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Conformational Space of Tetrakis(2-naphthalenyl)ethene – a Naphthologous AIE Luminogen

Sergey Pogodin • Naela Assadi • Israel Agranat Organic Chemistry, Institute of Chemistry, The Hebrew University of Jerusalem, Philadelphia Building, #201/205, Edmond J. Safra Campus, Jerusalem 91904, Israel Email: [email protected]

Table of content

Table S1. Total and relative energies of B3LYP/6-31G(d) optimized conformations of 2-NA4E. 2 Table S2. Total and relative energies of B3LYP/6-31G(d) optimized conformations of Ph4E. 3 Coordinates of the optimized conformations of 2-NA4E. 4 Coordinates of the optimized conformations of Ph4E. 19

1 Table S1. Total and relative energies of B3LYP/6-31G(d) optimized conformations of 2-NA4E. Electronic energy including thermal correction Zero Point to

ΔETot ΔZPE ΔH298 ΔG298 ETot Energy Energy (E) Enthalpy (H) Free energy (G) kJ/mo kJ/mo kJ/mo kJ/mo Hartree Hartree Hartree Hartree l l l l Hartree m n p q D2 1Z ,1Z ,2Z ,2Z M 0.98 0.47 0.70 2.34 -1617.38203809 -1616.817823 -1616.786590 -1616.785646 -1616.882083 m n p q D2 1E ,1E ,2E ,2E M 0.95 1.30 1.19 5.02 -1617.38205239 -1616.817507 -1616.786402 -1616.785458 -1616.881061 m n p q C2 1Z ,1Z ,2E ,2E M 0.00 0.29 0.21 2.25 -1617.38241284 -1616.817894 -1616.786776 -1616.785832 -1616.882118 m n p q C2 1Z ,1E ,2E ,2Z M 0.43 0.37 0.44 1.24 -1617.38224886 -1616.817862 -1616.786690 -1616.785745 -1616.882500 m n p q C2 1Z ,1E ,2Z ,2E M -0.87 -0.59 -0.72 2.02 -1617.38274381 -1616.818228 -1616.787134 -1616.786189 -1616.882206 m n p q C1 1Z ,1E ,2E ,2E M 0.03 0.40 0.19 1.68 -1617.38240160 -1616.817850 -1616.786784 -1616.785839 -1616.882335 m n p q C1 1Z ,1Z ,2Z ,2E M 0.00 0.00 0.00 0.00 -1617.38241238 -1616.818003 -1616.786857 -1616.785913 -1616.882974 m n p q C1 1Z ,1E ,2E ,2E TS 32.00 30.48 28.86 32.11 -1617.37022255 -1616.806392 -1616.775866 -1616.774922 -1616.870745 C2 -1617.37015834 m n p q h 1Z ,1Z ,2Z ,2Z SP2 32.17 30.21 26.33 38.95 -1616.806496 -1616.776830 -1616.775886 -1616.868140 C2 -1617.36967355 m n p q h 1E ,1E ,2E ,2E SP2 33.45 31.13 27.38 39.61 -1616.806147 -1616.776427 -1616.775483 -1616.867888 m n p q Ci 1Z ,1E ,2Z ,2E TS 31.27 29.88 28.28 31.21 -1617.37050263 -1616.806622 -1616.776087 -1616.775143 -1616.871086 C2 -1617.36877519 m n p q v 1Z ,1Z ,2Z ,2Z SP3 35.80 32.28 26.67 42.33 -1616.805710 -1616.776699 -1616.775755 -1616.866851 m n p q Cs 1Z ,1Z ,2E ,2E SP2 33.21 30.87 27.14 37.01 -1617.36976241 -1616.806246 -1616.776520 -1616.775576 -1616.868876 m n p q Cs 1Z ,1Z ,2Z ,2Z SP2 31.98 30.06 26.21 36.89 -1617.37023286 -1616.806552 -1616.776875 -1616.775931 -1616.868922

2 Table S2. Total and relative energies of B3LYP/6-31G(d) optimized conformations of Ph4E. Electronic energy including thermal correction Zero Point to

ΔETot ΔZPE ΔH298 ΔG298 ETot Energy Energy (E) Enthalpy (H) Free energy (G) kJ/mo kJ/mo kJ/mo kJ/mo Hartree Hartree Hartree Hartree l l l l Hartree m n p q D2 1M ,1M ,2M ,2M M 0.00 0.00 0.00 1.73 -1002.80512806 -1002.428139 -1002.407525 -1002.406581 -1002.478260 m n p q C2 1M ,1M ,2M ,2M M -0.23 0.11 -0.07 1.06 -1002.80521429 -1002.428100 -1002.407550 -1002.406606 -1002.478514 m n p q C2 1M ,1M ,2M ,2M M 0.00 0.00 0.00 0.01 -1002.80512794 -1002.428139 -1002.407525 -1002.406581 -1002.478916 m n p q C2 1M ,1M ,2M ,2M M 0.00 0.00 0.00 0.00 -1002.80512796 -1002.428140 -1002.407525 -1002.406581 -1002.478919 C2 -1002.79383117 m n p q h 1P ,1M ,2M ,2P SP2 29.66 27.39 23.71 32.66 -1002.417709 -1002.398493 -1002.397549 -1002.466480 m n p q Ci 1P ,1M ,2M ,2P TS 29.10 27.75 26.11 27.48 -1002.79404252 -1002.417571 -1002.397580 -1002.396636 -1002.468454 C2 -1002.79306085 m n p q v 1P ,1M ,2P ,2M SP3 31.68 28.28 22.82 34.99 -1002.417369 -1002.398832 -1002.397888 -1002.465593 m n p q Cs 1P ,1P ,2M ,2M SP2 30.86 28.33 24.85 30.44 -1002.79337490 -1002.417351 -1002.398061 -1002.397117 -1002.467324

3 Coordinates of the optimized C 37 r5337 21 a533721 25 d53372125 0 C 38 r5337 22 a533721 26 d53372125 0 C 39 r5337 23 a533721 27 d53372125 0 conformations of 2-NA4E. C 40 r5337 24 a533721 28 d53372125 0 H 33 r5733 17 a573317 13 d57331713 0 H 34 r5733 18 a573317 14 d57331713 0 2-NA4E, D2-ZZZZ, ΔG298=2.34 kJ/mol H 35 r5733 19 a573317 15 d57331713 0 0 1 H 36 r5733 20 a573317 16 d57331713 0 C H 37 r6137 21 a613721 25 d61372125 0 C 1 r21 H 38 r6137 22 a613721 26 d61372125 0 X 1 1. 2 90. H 39 r6137 23 a613721 27 d61372125 0 X 2 1. 1 90. 3 d4213 0 H 40 r6137 24 a613721 28 d61372125 0 C 1 r51 2 a512 3 90. 0 H 49 r6549 33 a654933 17 d65493317 0 C 1 r51 2 a512 3 -90. 0 H 50 r6549 34 a654933 18 d65493317 0 C 2 r51 1 a512 4 90. 0 H 51 r6549 35 a654933 19 d65493317 0 C 2 r51 1 a512 4 -90. 0 H 52 r6549 36 a654933 20 d65493317 0 C 5 r95 1 a951 2 d9512 0 H 53 r6953 37 a695337 21 d69533721 0 C 6 r95 1 a951 2 d9512 0 H 54 r6953 38 a695337 22 d69533721 0 C 7 r95 2 a951 1 d9512 0 H 55 r6953 39 a695337 23 d69533721 0 C 8 r95 2 a951 1 d9512 0 H 56 r6953 40 a695337 24 d69533721 0 C 5 r135 9 a1359 1 d13591 0 C 6 r135 10 a1359 1 d13591 0 r21=1.36539421 C 7 r135 11 a1359 2 d13591 0 r51=1.49429018 C 8 r135 12 a1359 2 d13591 0 r95=1.42708305 C 13 r1713 5 a17135 9 d171359 0 r135=1.38446835 C 14 r1713 6 a17135 10 d171359 0 r1713=1.41865216 C 15 r1713 7 a17135 11 d171359 0 r2117=1.43290372 C 16 r1713 8 a17135 12 d171359 0 r2521=1.4210129 C 17 r2117 13 a211713 5 d2117135 0 r2913=1.08657669 C 18 r2117 14 a211713 6 d2117135 0 r3317=1.42177118 C 19 r2117 15 a211713 7 d2117135 0 r3721=1.4196523 C 20 r2117 16 a211713 8 d2117135 0 r4125=1.08773314 C 21 r2521 17 a252117 13 d25211713 0 r459=1.08621603 C 22 r2521 18 a252117 14 d25211713 0 r4933=1.37666496 C 23 r2521 19 a252117 15 d25211713 0 r5337=1.37724199 C 24 r2521 20 a252117 16 d25211713 0 r5733=1.08750125 H 13 r2913 5 a29135 9 d291359 0 r6137=1.08769396 H 14 r2913 6 a29135 10 d291359 0 r6549=1.0867147 H 15 r2913 7 a29135 11 d291359 0 r6953=1.08671114 H 16 r2913 8 a29135 12 d291359 0 a512=122.91582779 C 17 r3317 13 a331713 5 d3317135 0 a951=119.73913659 C 18 r3317 14 a331713 6 d3317135 0 a1359=118.44093538 C 19 r3317 15 a331713 7 d3317135 0 a17135=121.79606504 C 20 r3317 16 a331713 8 d3317135 0 a211713=119.11111598 C 21 r3721 17 a372117 13 d37211713 0 a252117=118.38405407 C 22 r3721 18 a372117 14 d37211713 0 a29135=119.61209412 C 23 r3721 19 a372117 15 d37211713 0 a331713=122.10002117 C 24 r3721 20 a372117 16 d37211713 0 a372117=119.00800807 H 25 r4125 21 a412521 17 d41252117 0 a412521=118.79954369 H 26 r4125 22 a412521 18 d41252117 0 a4595=118.81980694 H 27 r4125 23 a412521 19 d41252117 0 a493317=120.82111836 H 28 r4125 24 a412521 20 d41252117 0 a533721=120.79379425 H 9 r459 5 a4595 13 d459513 0 a573317=118.69750534 H 10 r459 6 a4595 14 d459513 0 a613721=118.75407563 H 11 r459 7 a4595 15 d459513 0 a654933=120.06706545 H 12 r459 8 a4595 16 d459513 0 a695337=120.10819073 C 33 r4933 17 a493317 13 d49331713 0 d4213=168.18570093 C 34 r4933 18 a493317 14 d49331713 0 d9512=-228.43162514 C 35 r4933 19 a493317 15 d49331713 0 d13591=-177.03795194 C 36 r4933 20 a493317 16 d49331713 0 d171359=-1.1078051

4 d2117135=0.16913284 H 9 r459 5 a4595 13 d459513 0 d25211713=0.33480196 H 10 r459 6 a4595 14 d459513 0 d291359=179.02458831 H 11 r459 7 a4595 15 d459513 0 d3317135=-179.99407984 H 12 r459 8 a4595 16 d459513 0 d37211713=-180.00485556 C 33 r4933 17 a493317 13 d49331713 0 d41252117=179.79190517 C 34 r4933 18 a493317 14 d49331713 0 d459513=-178.78937899 C 35 r4933 19 a493317 15 d49331713 0 d49331713=179.99745561 C 36 r4933 20 a493317 16 d49331713 0 d53372125=179.58371225 C 37 r5337 21 a533721 25 d53372125 0 d57331713=0.27646408 C 38 r5337 22 a533721 26 d53372125 0 d61372125=-0.38399488 C 39 r5337 23 a533721 27 d53372125 0 d65493317=180.16551522 C 40 r5337 24 a533721 28 d53372125 0 d69533721=179.97786599 H 33 r5733 17 a573317 13 d57331713 0 H 34 r5733 18 a573317 14 d57331713 0

2-NA4E, D2-EEEE, ΔG298=5.02 kJ/mol H 35 r5733 19 a573317 15 d57331713 0 0 1 H 36 r5733 20 a573317 16 d57331713 0 C H 37 r6137 21 a613721 25 d61372125 0 C 1 r21 H 38 r6137 22 a613721 26 d61372125 0 X 1 1. 2 90. H 39 r6137 23 a613721 27 d61372125 0 X 2 1. 1 90. 3 d4213 0 H 40 r6137 24 a613721 28 d61372125 0 C 1 r51 2 a512 3 90. 0 H 49 r6549 33 a654933 17 d65493317 0 C 1 r51 2 a512 3 -90. 0 H 50 r6549 34 a654933 18 d65493317 0 C 2 r51 1 a512 4 90. 0 H 51 r6549 35 a654933 19 d65493317 0 C 2 r51 1 a512 4 -90. 0 H 52 r6549 36 a654933 20 d65493317 0 C 5 r95 1 a951 2 d9512 0 H 53 r6953 37 a695337 21 d69533721 0 C 6 r95 1 a951 2 d9512 0 H 54 r6953 38 a695337 22 d69533721 0 C 7 r95 2 a951 1 d9512 0 H 55 r6953 39 a695337 23 d69533721 0 C 8 r95 2 a951 1 d9512 0 H 56 r6953 40 a695337 24 d69533721 0 C 5 r135 9 a1359 1 d13591 0 C 6 r135 10 a1359 1 d13591 0 r21=1.37056515 C 7 r135 11 a1359 2 d13591 0 r51=1.493685 C 8 r135 12 a1359 2 d13591 0 r95=1.42742261 C 13 r1713 5 a17135 9 d171359 0 r135=1.38659583 C 14 r1713 6 a17135 10 d171359 0 r1713=1.41801633 C 15 r1713 7 a17135 11 d171359 0 r2117=1.43285959 C 16 r1713 8 a17135 12 d171359 0 r2521=1.4208579 C 17 r2117 13 a211713 5 d2117135 0 r2913=1.0869671 C 18 r2117 14 a211713 6 d2117135 0 r3317=1.42202079 C 19 r2117 15 a211713 7 d2117135 0 r3721=1.41967028 C 20 r2117 16 a211713 8 d2117135 0 r4125=1.08764576 C 21 r2521 17 a252117 13 d25211713 0 r459=1.08492415 C 22 r2521 18 a252117 14 d25211713 0 r4933=1.37657143 C 23 r2521 19 a252117 15 d25211713 0 r5337=1.37731995 C 24 r2521 20 a252117 16 d25211713 0 r5733=1.08757624 H 13 r2913 5 a29135 9 d291359 0 r6137=1.08765959 H 14 r2913 6 a29135 10 d291359 0 r6549=1.08671345 H 15 r2913 7 a29135 11 d291359 0 r6953=1.08671396 H 16 r2913 8 a29135 12 d291359 0 a512=122.39561241 C 17 r3317 13 a331713 5 d3317135 0 a951=120.7695943 C 18 r3317 14 a331713 6 d3317135 0 a1359=118.20654831 C 19 r3317 15 a331713 7 d3317135 0 a17135=121.96447637 C 20 r3317 16 a331713 8 d3317135 0 a211713=119.07682257 C 21 r3721 17 a372117 13 d37211713 0 a252117=118.3141139 C 22 r3721 18 a372117 14 d37211713 0 a29135=119.63491422 C 23 r3721 19 a372117 15 d37211713 0 a331713=122.11680507 C 24 r3721 20 a372117 16 d37211713 0 a372117=118.99931376 H 25 r4125 21 a412521 17 d41252117 0 a412521=118.80293705 H 26 r4125 22 a412521 18 d41252117 0 a4595=118.81031534 H 27 r4125 23 a412521 19 d41252117 0 a493317=120.8139355 H 28 r4125 24 a412521 20 d41252117 0 a533721=120.78722394

5 a573317=118.7015914 C 21 r3721 17 a372117 13 d37211713 0 a613721=118.74496526 C 22 r3721 18 a372117 14 d37211713 0 a654933=120.08050588 C 23 r3721a 19 a372117a 15 d37211713a 0 a695337=120.10055042 C 24 r3721a 20 a372117a 16 d37211713a 0 d4213=193.34825042 H 25 r4125 21 a412521 17 d41252117 0 d9512=46.85460568 H 26 r4125 22 a412521 18 d41252117 0 d13591=-177.48399001 C 27 r4125a 11 a412521a 7 d41252117a 0 d171359=-1.60868241 C 28 r4125a 12 a412521a 8 d41252117a 0 d2117135=1.08623065 H 9 r459 5 a4595 13 d459513 0 d25211713=0.14586591 H 10 r459 6 a4595 14 d459513 0 d291359=178.7173827 H 11 r459a 7 a4595a 15 d459513a 0 d3317135=-179.00981596 H 12 r459a 8 a4595a 16 d459513a 0 d37211713=-180.18259481 C 33 r4933 17 a493317 13 d49331713 0 d41252117=178.89591941 C 34 r4933 18 a493317 14 d49331713 0 d459513=-178.55868431 C 39 r4933a 23 a493317a 19 d49331713a 0 d49331713=180.04342241 C 40 r4933a 24 a493317a 20 d49331713a 0 d53372125=179.84451935 C 37 r5337 21 a533721 25 d53372125 0 d57331713=0.0276382 C 38 r5337 22 a533721 26 d53372125 0 d61372125=-0.251924 C 43 r5337a 27 a533721a 11 d53372125a 0 d65493317=180.03172915 C 44 r5337a 28 a533721a 12 d53372125a 0 d69533721=179.88855839 H 33 r5733 17 a573317 13 d57331713 0 H 34 r5733 18 a573317 14 d57331713 0

2-NA4E, C2-ZZEE, ΔG298=2.25 kJ/mol H 39 r5733a 23 a573317a 19 d57331713a 0 0 1 H 40 r5733a 24 a573317a 20 d57331713a 0 C H 37 r6137 21 a613721 25 d61372125 0 C 1 r21 H 38 r6137 22 a613721 26 d61372125 0 X 1 1. 2 90. H 43 r6137a 27 a613721a 11 d61372125a 0 X 2 1. 1 90. 3 d4213 0 H 44 r6137a 28 a613721a 12 d61372125a 0 C 1 r51 2 a512 3 90. 0 H 49 r6549 33 a654933 17 d65493317 0 C 1 r51 2 a512 3 -90. 0 H 50 r6549 34 a654933 18 d65493317 0 C 2 r51a 1 a512a 4 90. 0 H 51 r6549a 39 a654933a 23 d65493317a 0 C 2 r51a 1 a512a 4 -90. 0 H 52 r6549a 40 a654933a 24 d65493317a 0 C 5 r95 1 a951 2 d9512 0 H 53 r6953 37 a695337 21 d69533721 0 C 6 r95 1 a951 2 d9512 0 H 54 r6953 38 a695337 22 d69533721 0 C 7 r95a 2 a951a 1 d9512a 0 H 55 r6953a 43 a695337a 27 d69533721a 0 C 8 r95a 2 a951a 1 d9512a 0 H 56 r6953a 44 a695337a 28 d69533721a 0 C 5 r135 9 a1359 1 d13591 0 C 6 r135 10 a1359 1 d13591 0 r21=1.36828368 C 7 r135a 11 a1359a 2 d13591a 0 r51=1.4929063 C 8 r135a 12 a1359a 2 d13591a 0 r51a=1.49478689 C 13 r1713 5 a17135 9 d171359 0 r95=1.42779827 C 14 r1713 6 a17135 10 d171359 0 r95a=1.38596233 C 15 r1713a 7 a17135a 11 d171359a 0 r135=1.38486382 C 16 r1713a 8 a17135a 12 d171359a 0 r135a=1.42731935 C 17 r2117 13 a211713 5 d2117135 0 r1713=1.41855474 C 18 r2117 14 a211713 6 d2117135 0 r1713a=1.37357317 C 19 r2117a 15 a211713a 7 d2117135a 0 r2117=1.43268139 C 20 r2117a 16 a211713a 8 d2117135a 0 r2117a=1.42106432 C 21 r2521 17 a252117 13 d25211713 0 r2521=1.42133434 C 22 r2521 18 a252117 14 d25211713 0 r2521a=1.43250036 C 23 r2521a 19 a252117a 15 d25211713a 0 r2913=1.08636812 C 24 r2521a 20 a252117a 16 d25211713a 0 r2913a=1.08510983 H 13 r2913 5 a29135 9 d291359 0 r3317=1.42161335 H 14 r2913 6 a29135 10 d291359 0 r3317a=1.08763264 H 15 r2913a 7 a29135a 11 d291359a 0 r3721=1.41958468 H 16 r2913a 8 a29135a 12 d291359a 0 r3721a=1.41959986 C 17 r3317 13 a331713 5 d3317135 0 r4125=1.08772589 C 18 r3317 14 a331713 6 d3317135 0 r4125a=1.4218299 H 19 r3317a 15 a331713a 7 d3317135a 0 r459=1.08621403 H 20 r3317a 16 a331713a 8 d3317135a 0 r459a=1.08703324

6 r4933=1.37672185 d3317135a=-180.57342749 r4933a=1.37742524 d37211713=-179.87804904 r5337=1.37742172 d37211713a=-179.66799142 r5337a=1.37672558 d41252117=179.79165466 r5733=1.08745214 d41252117a=179.15804631 r5733a=1.08765239 d459513=-178.83431856 r6137=1.08768138 d459513a=-178.66917234 r6137a=1.08758513 d49331713=179.87557783 r6549=1.08669352 d49331713a=180.25906701 r6549a=1.0867367 d53372125=179.59154424 r6953=1.08672599 d53372125a=179.82631329 r6953a=1.08673931 d57331713=0.16470425 a512=122.82397651 d57331713a=0.3488129 a512a=122.431427 d61372125=-0.36448057 a951=119.92999294 d61372125a=-0.10984018 a951a=120.82675341 d65493317=180.17885095 a1359=118.38360737 d65493317a=180.10750358 a1359a=118.22877878 d69533721=179.98668105 a17135=121.83215856 d69533721a=180.0120301 a17135a=121.23955428 a211713=119.12488749 2-NA4E, C2-ZEEZ, ΔG298=1.24 kJ/mol a211713a=121.16661982 0 1 a252117=118.36059922 C a252117a=118.30998608 C 1 r21 a29135=119.61053342 X 1 1. 2 90. a29135a=118.84483525 X 2 1. 1 90. 3 d4213 0 a331713=122.06005001 C 1 r51 2 a512 3 d5123 0 a331713a=120.02517197 C 1 r51a 2 a512a 3 -d5123 0 a372117=119.00098821 C 2 r51 1 a512 4 d5123 0 a372117a=122.68445624 C 2 r51a 1 a512a 4 -d5123 0 a412521=118.79769154 C 5 r95 1 a951 2 d9512 0 a412521a=122.11128988 C 6 r95a 1 a951a 2 d9512a 0 a4595=118.82757897 C 7 r95 2 a951 1 d9512 0 a4595a=119.63877237 C 8 r95a 2 a951a 1 d9512a 0 a493317=120.81324895 C 5 r135 9 a1359 1 d13591 0 a493317a=120.78562971 C 6 r135a 10 a1359a 1 d13591a 0 a533721=120.78059979 C 7 r135 11 a1359 2 d13591 0 a533721a=120.81241504 C 8 r135a 12 a1359a 2 d13591a 0 a573317=118.71479085 C 13 r1713 5 a17135 9 d171359 0 a573317a=118.76083036 C 14 r1713a 6 a17135a 10 d171359a 0 a613721=118.76606013 C 15 r1713 7 a17135 11 d171359 0 a613721a=118.71367034 C 16 r1713a 8 a17135a 12 d171359a 0 a654933=120.07493408 C 17 r2117 13 a211713 5 d2117135 0 a654933a=120.10452089 C 18 r2117a 14 a211713a 6 d2117135a 0 a695337=120.09261219 C 19 r2117 15 a211713 7 d2117135 0 a695337a=120.08440264 C 20 r2117a 16 a211713a 8 d2117135a 0 d4213=167.53219271 C 21 r2521 17 a252117 13 d25211713 0 d9512=-227.2390843 C 22 r2521a 18 a252117a 14 d25211713a 0 d9512a=-224.78311592 C 23 r2521 19 a252117 15 d25211713 0 d13591=-177.38152891 C 24 r2521a 20 a252117a 16 d25211713a 0 d13591a=-177.28326961 H 13 r2913 5 a29135 9 d291359 0 d171359=-1.21599262 H 14 r2913a 6 a29135a 10 d291359a 0 d171359a=-0.88810197 H 15 r2913 7 a29135 11 d291359 0 d2117135=0.17833388 H 16 r2913a 8 a29135a 12 d291359a 0 d2117135a=-0.25063013 C 17 r3317 13 a331713 5 d3317135 0 d25211713=0.42765361 C 22 r3317a 18 a331713a 14 d3317135a 0 d25211713a=0.75327948 C 19 r3317 15 a331713 7 d3317135 0 d291359=179.02470914 C 24 r3317a 20 a331713a 16 d3317135a 0 d291359a=178.57320782 C 21 r3721 17 a372117 13 d37211713 0 d3317135=-179.91630714 C 26 r3721a 10 a372117a 6 d37211713a 0

7 C 23 r3721 19 a372117 15 d37211713 0 r5337=1.37736574 C 28 r3721a 12 a372117a 8 d37211713a 0 r5337a=1.37665051 H 25 r4125 21 a412521 17 d41252117 0 r5733=1.08750885 H 18 r4125a 14 a412521a 6 d41252117a 0 r5733a=1.08765743 H 27 r4125 23 a412521 19 d41252117 0 r6137=1.08770608 H 20 r4125a 16 a412521a 8 d41252117a 0 r6137a=1.08755768 H 9 r459 5 a4595 13 d459513 0 r6549=1.08672006 H 10 r459a 6 a4595a 14 d459513a 0 r6549a=1.08671607 H 11 r459 7 a4595 15 d459513 0 r6953=1.08671641 H 12 r459a 8 a4595a 16 d459513a 0 r6953a=1.08671028 C 33 r4933 17 a493317 13 d49331713 0 a512=122.42206363 C 34 r4933a 22 a493317a 18 d49331713a 0 a512a=122.93894788 C 35 r4933 19 a493317 15 d49331713 0 a951=119.95740028 C 36 r4933a 24 a493317a 20 d49331713a 0 a951a=120.66199725 C 37 r5337 21 a533721 25 d53372125 0 a1359=118.43437717 C 38 r5337a 26 a533721a 10 d53372125a 0 a1359a=118.2472358 C 39 r5337 23 a533721 27 d53372125 0 a17135=121.8158281 C 40 r5337a 28 a533721a 12 d53372125a 0 a17135a=121.20383495 H 33 r5733 17 a573317 13 d57331713 0 a211713=119.09843542 H 34 r5733a 22 a573317a 18 d57331713a 0 a211713a=121.18705841 H 35 r5733 19 a573317 15 d57331713 0 a252117=118.37639146 H 36 r5733a 24 a573317a 20 d57331713a 0 a252117a=118.32418814 H 37 r6137 21 a613721 25 d61372125 0 a29135=119.59679559 H 38 r6137a 26 a613721a 10 d61372125a 0 a29135a=118.84270983 H 39 r6137 23 a613721 27 d61372125 0 a331713=122.10807061 H 40 r6137a 28 a613721a 12 d61372125a 0 a331713a=122.67829069 H 49 r6549 33 a654933 17 d65493317 0 a372117=119.00932025 H 50 r6549a 34 a654933a 18 d65493317a 0 a372117a=122.11827494 H 51 r6549 35 a654933 19 d65493317 0 a412521=118.78929044 H 52 r6549a 36 a654933a 20 d65493317a 0 a412521a=120.02071776 H 53 r6953 37 a695337 21 d69533721 0 a4595=118.84647574 H 54 r6953a 38 a695337a 22 d69533721a 0 a4595a=119.59486196 H 55 r6953 39 a695337 23 d69533721 0 a493317=120.82332788 H 56 r6953a 40 a695337a 24 d69533721a 0 a493317a=120.7819255 a533721=120.79335051 r21=1.36774487 a533721a=120.80971722 r51=1.49426928 a573317=118.69790838 r51a=1.49337243 a573317a=118.75441793 r95=1.42728109 a613721=118.75537722 r95a=1.38658521 a613721a=118.70422372 r135=1.38407188 a654933=120.06742294 r135a=1.42762471 a654933a=120.09212566 r1713=1.41901834 a695337=120.10537376 r1713a=1.37351006 a695337a=120.08127697 r2117=1.4327299 d4213=167.48421506 r2117a=1.42110463 d5123=90.1860112 r2521=1.42134897 d9512=-230.34055819 r2521a=1.43275389 d9512a=-222.55654925 r2913=1.08661649 d13591=-177.31549293 r2913a=1.0849037 d13591a=-177.01392009 r3317=1.42156237 d171359=-1.04338171 r3317a=1.41959969 d171359a=-1.07273238 r3721=1.4195287 d2117135=0.09629272 r3721a=1.42185362 d2117135a=-0.20841597 r4125=1.0877352 d25211713=0.36198035 r4125a=1.08765183 d25211713a=0.82651676 r459=1.0861827 d291359=179.09157271 r459a=1.08703808 d291359a=178.39712111 r4933=1.37679203 d3317135=-180.05448285 r4933a=1.37740545 d3317135a=-179.55342843

8 d37211713=-179.97144121 C 24 r3721a 20 a372117a 16 d37211713a 0 d37211713a=-181.0153344 H 25 r4125 21 a412521 17 d41252117 0 d41252117=179.85387087 H 26 r4125a 22 a412521a 18 d41252117a 0 d41252117a=179.49080406 H 27 r4125 23 a412521 19 d41252117 0 d459513=-178.82652249 H 28 r4125a 24 a412521a 20 d41252117a 0 d459513a=-178.62741727 H 9 r459 5 a4595 13 d459513 0 d49331713=179.97026914 H 10 r459a 6 a4595a 14 d459513a 0 d49331713a=180.21277191 H 11 r459 7 a4595 15 d459513 0 d53372125=179.57427024 H 12 r459a 8 a4595a 16 d459513a 0 d53372125a=179.93887074 C 33 r4933 17 a493317 13 d49331713 0 d57331713=0.24681759 C 34 r4933a 18 a493317a 14 d49331713a 0 d57331713a=0.29746488 C 35 r4933 19 a493317 15 d49331713 0 d61372125=-0.39963685 C 36 r4933a 20 a493317a 16 d49331713a 0 d61372125a=-0.04473598 C 37 r5337 21 a533721 25 d53372125 0 d65493317=180.1691997 C 38 r5337a 22 a533721a 26 d53372125a 0 d65493317a=179.88944484 C 39 r5337 23 a533721 27 d53372125 0 d69533721=179.98111109 C 40 r5337a 24 a533721a 28 d53372125a 0 d69533721a=179.99684793 H 33 r5733 17 a573317 13 d57331713 0 H 34 r5733a 18 a573317a 14 d57331713a 0 2-NA4E, C2-ZEZE, ΔG298=2.02 kJ/mol H 35 r5733 19 a573317 15 d57331713 0 0 1 H 36 r5733a 20 a573317a 16 d57331713a 0 C H 37 r6137 21 a613721 25 d61372125 0 C 1 r21 H 38 r6137a 22 a613721a 26 d61372125a 0 X 1 1. 2 90. H 39 r6137 23 a613721 27 d61372125 0 X 2 1. 1 90. 3 d4213 0 H 40 r6137a 24 a613721a 28 d61372125a 0 C 1 r51 2 a512 3 d5123 0 H 49 r6549 33 a654933 17 d65493317 0 C 1 r51a 2 a512a 3 -d5123 0 H 50 r6549a 34 a654933a 18 d65493317a 0 C 2 r51 1 a512 4 d5123 0 H 51 r6549 35 a654933 19 d65493317 0 C 2 r51a 1 a512a 4 -d5123 0 H 52 r6549a 36 a654933a 20 d65493317a 0 C 5 r95 1 a951 2 d9512 0 H 53 r6953 37 a695337 21 d69533721 0 C 6 r95a 1 a951a 2 d9512a 0 H 54 r6953a 38 a695337a 22 d69533721a 0 C 7 r95 2 a951 1 d9512 0 H 55 r6953 39 a695337 23 d69533721 0 C 8 r95a 2 a951a 1 d9512a 0 H 56 r6953a 40 a695337a 24 d69533721a 0 C 5 r135 9 a1359 1 d13591 0 C 6 r135a 10 a1359a 1 d13591a 0 r21=1.36850514 C 7 r135 11 a1359 2 d13591 0 r51=1.49374746 C 8 r135a 12 a1359a 2 d13591a 0 r51a=1.49336183 C 13 r1713 5 a17135 9 d171359 0 r95=1.42770478 C 14 r1713a 6 a17135a 10 d171359a 0 r95a=1.4278437 C 15 r1713 7 a17135 11 d171359 0 r135=1.38607822 C 16 r1713a 8 a17135a 12 d171359a 0 r135a=1.38451732 C 17 r2117 13 a211713 5 d2117135 0 r1713=1.41863531 C 18 r2117a 14 a211713a 6 d2117135a 0 r1713a=1.41895133 C 19 r2117 15 a211713 7 d2117135 0 r2117=1.43230112 C 20 r2117a 16 a211713a 8 d2117135a 0 r2117a=1.43253184 C 21 r2521 17 a252117 13 d25211713 0 r2521=1.42153845 C 22 r2521a 18 a252117a 14 d25211713a 0 r2521a=1.4217278 C 23 r2521 19 a252117 15 d25211713 0 r2913=1.08709577 C 24 r2521a 20 a252117a 16 d25211713a 0 r2913a=1.08636622 H 13 r2913 5 a29135 9 d291359 0 r3317=1.42162142 H 14 r2913a 6 a29135a 10 d291359a 0 r3317a=1.42141445 H 15 r2913 7 a29135 11 d291359 0 r3721=1.41934966 H 16 r2913a 8 a29135a 12 d291359a 0 r3721a=1.41942254 C 17 r3317 13 a331713 5 d3317135 0 r4125=1.08764713 C 18 r3317a 14 a331713a 6 d3317135a 0 r4125a=1.08772521 C 19 r3317 15 a331713 7 d3317135 0 r459=1.08503623 C 20 r3317a 16 a331713a 8 d3317135a 0 r459a=1.0861052 C 21 r3721 17 a372117 13 d37211713 0 r4933=1.37690337 C 22 r3721a 18 a372117a 14 d37211713a 0 r4933a=1.37689256 C 23 r3721 19 a372117 15 d37211713 0 r5337=1.37764022

9 r5337a=1.37756651 d37211713a=-180.10708358 r5733=1.08760346 d41252117=178.92045818 r5733a=1.0874698 d41252117a=180.17377715 r6137=1.08766014 d459513=-178.44039055 r6137a=1.08767068 d459513a=-181.1846126 r6549=1.08673742 d49331713=180.18573392 r6549a=1.086694 d49331713a=180.12029483 r6953=1.08671865 d53372125=179.72384584 r6953a=1.08671499 d53372125a=180.387925 a512=123.0489385 d57331713=0.13964622 a512a=122.27302103 d57331713a=-0.16719385 a951=121.12027168 d61372125=-0.34637575 a951a=120.13673118 d61372125a=0.36062263 a1359=118.21449062 d65493317=180.00744841 a1359a=118.40223795 d65493317a=179.82254456 a17135=121.98254939 d69533721=179.91103537 a17135a=121.83862751 d69533721a=180.00944546 a211713=119.06324204 a211713a=119.10511581 2-NA4E, C1-ZEEE, ΔG298=1.68 kJ/mol a252117=118.2980081 0 1 a252117a=118.36277178 C 0.0255905819 -0.010773005 0.1695596659 a29135=119.6130712 C -0.0126343148 -0.2070874348 1.5246093877 a29135a=119.57403724 C 0.2940217883 -1.1200183101 -0.7939555004 a331713=122.12275711 C -0.1951455152 1.3311884053 -0.4502421756 a331713a=122.07740675 C 0.0078552227 0.926611941 2.4963267051 a372117=119.01196214 C -0.0750171359 -1.5618449432 2.1486461751 a372117a=119.00615496 C 1.3590338738 -2.0433225663 -0.5683591136 a412521=118.79094435 C -1.2964885145 2.1477722516 -0.0534300658 a412521a=118.79557537 C -0.9435843241 0.9765310256 3.5598271114 a4595=118.88123397 C -0.9731839478 -2.5578693142 1.6588414967 a4595a=118.85835934 C -0.4494728527 -1.2490949669 -1.9574471373 a493317=120.81404185 C 0.6309044422 1.792172979 -1.463175037 a493317a=120.8104722 C 0.9685782072 1.921120017 2.425522785 a533721=120.78591755 C 0.6929904987 -1.8631725417 3.2633441149 a533721a=120.78139167 C -0.1999869232 -2.2809472112 -2.8974177895 a573317=118.7239291 C 0.428446887 3.0521983092 -2.0823488904 a573317a=118.72435898 C 1.013042455 2.9872748811 3.3607889196 a613721=118.76641599 C 0.6308150681 -3.1297547952 3.8983357538 a613721a=118.7749536 C 0.8644176045 -3.2073067998 -2.6485560521 a654933=120.07699892 C -0.6751820468 3.8640242042 -1.6642918303 a654933a=120.06799363 C 0.0380812788 3.0353792517 4.4092447255 a695337=120.09831624 C -0.267047728 -4.1216707232 3.386334492 a695337a=120.09582877 C 1.6333679756 -3.0476809278 -1.46446168 d4213=12.53042254 C -1.5276746823 3.367238597 -0.6413836228 d5123=89.84589628 C -0.9348230581 2.0009021303 4.4748506595 d9512=46.44290662 C -1.0649644008 -3.7903305965 2.2579235731 d9512a=-131.4859612 H -1.2522319313 -0.5458621896 -2.163393448 d13591=-176.7361564 H 1.4642530506 1.1797409916 -1.7980293585 d13591a=-182.29701129 H 1.7114186862 1.8931439091 1.6332412697 d171359=-1.56037217 H 1.3700857928 -1.1147409767 3.6671851913 d171359a=1.0898435 C -0.9706557125 -2.425161096 -4.0838354349 d2117135=1.03647057 C 1.2848739684 3.5363194084 -3.1088673077 d2117135a=-0.09535723 C 1.9967218246 4.0111613454 3.2923259234 d25211713=0.12382113 C 1.4292523204 -3.4473464862 5.0311455316 d25211713a=-0.40274638 C 1.115149516 -4.2372267757 -3.5929539584 d291359=178.74201499 C -0.8790482519 5.1227817276 -2.288029979 d291359a=180.95384581 C 0.0827924995 4.1043040275 5.3420647466 d3317135=-179.16090241 C -0.3318591355 -5.3872071434 4.0260907628 d3317135a=-180.00901235 H 2.4552490877 -3.7348409139 -1.2765010232 d37211713=-180.28481048 H -2.3781511101 3.9692810993 -0.3296141146

10 H -1.6768643495 2.0291268653 5.2696472463 H 1.6195719913 2.1624108241 0.2891915798 H -1.7623681673 -4.5312759283 1.8737162896 H 1.3432822106 0.8532491651 3.6011283565 H 1.9636268389 -1.9361310449 0.32604657 H 2.1245264713 -1.7333155576 1.1969955041 H -1.9629902341 1.7858775141 0.7226414444 C -1.8503109567 -4.5224290719 -1.0898249654 H -1.6889610849 0.1900379914 3.6340583322 C 1.8569855763 4.4829434831 -1.08120415 H -1.5971220891 -2.3245846229 0.8025829548 C 1.055482788 2.9585802227 5.271749647 C -0.7037288441 -3.4356637472 -4.9796345992 C 2.8952452804 -3.9438963437 2.5533101548 C 1.062458335 4.7630940916 -3.6928539963 C 0.0099353873 -4.807094791 -3.1712026795 C 2.0136443201 5.035542108 4.2122238105 C 0.0385402625 4.7306491253 -3.2040910662 C 1.3451969874 -4.6848779501 5.628474829 C -1.0969019646 4.6345124394 4.6149744544 C 0.349387539 -4.3509355648 -4.7321114452 C 1.1346504757 -4.6758792576 4.6117058934 C -0.0300650917 5.5645048751 -3.2787990114 H 1.6795233848 -2.6731883498 -3.4243638271 C 1.0474733882 5.0830840481 5.2471405645 H -1.5996628916 2.574934778 -3.4781092928 C 0.4561292039 -5.6646219313 5.1213563513 H -2.4788429571 3.8029546949 2.4213495196 H -1.7768992409 -1.7199528272 -4.2721692091 H -1.0017906124 -3.0061562075 4.8479531732 H 2.1214491536 2.9180485658 -3.4263070429 H 1.6564214122 -0.6367849392 -2.0407085542 H 2.7352232415 3.9738142788 2.4949625589 H -1.5805590887 0.5473804081 -2.0809143018 H 2.1094170612 -2.692624121 5.419178825 H -1.9746888607 1.8263331944 1.0487759632 H 1.9243100354 -4.9381207921 -3.4005569548 H -1.4497362945 -1.0151883848 3.4715505853 H -1.7188156505 5.7354699228 -1.9679783528 C -1.8486959163 -5.6570007998 -1.8695754732 H -0.6596621592 4.1379251897 6.136222719 C 1.8581816671 5.6124662874 -1.8684312698 H -1.0159868017 -6.1369524613 3.6351253593 C 0.7814087822 4.0691877669 6.0380371549 H -1.29939929 -3.534212941 -5.8832037564 C 3.1566470784 -5.0502078548 3.3300766196 H 1.7249231812 5.1215655444 -4.4762033586 C -0.9094119701 -5.8014103561 -2.9205770087 H 2.7693339023 5.8137250924 4.1466870794 C 0.9401568315 5.7379873474 -2.9401776826 H 1.9611283167 -4.9150839485 6.4936881266 C -0.3052103968 4.9156307262 5.706768241 H 0.5505351313 -5.1442814276 -5.4470244563 C 2.2680004486 -5.4202412824 4.3694867882 H -0.1954537858 6.5309538525 -3.7473959083 H -2.5685467419 -4.4106099517 -0.2809834768 H 1.0711228496 5.8966498108 5.9672138097 H 2.5586681631 4.3849909424 -0.2562450471 H 0.3984779478 -6.637684413 5.6017560948 H 1.8877112871 2.3057306364 5.5247463987 H 3.5746368869 -3.6589816301 1.753364619 2-NA4E, C1-ZZZE, ΔG298=0.0 kJ/mol H 0.7317872575 -4.9142083996 -3.9777734613 0 1 H -0.6665994681 4.8240041169 -4.0269554937 C 0.0190992937 -0.0264179116 0.0408089883 H -1.9321634442 5.2822288341 4.3584176346 C 0.0209548085 -0.0203260197 1.4081746309 H 0.4507296873 -4.9572793988 5.409282812 C 0.0248336118 -1.2851526647 -0.763806199 H -2.5688552387 -6.4485674863 -1.6803617889 C 0.0161109482 1.2241388733 -0.7746504601 H 2.5641127325 6.4143029015 -1.6693784389 C -0.2536287504 1.2058772841 2.2163027548 H 1.3983366343 4.3005010486 6.902256463 C 0.3047519046 -1.2466807826 2.21362178 H 4.0471997622 -5.6456509049 3.147502475 C 0.9482451163 -1.436031935 -1.8413764656 H -0.9180012478 -6.7018586457 -3.5289117899 C -0.886909718 1.3567908452 -1.8724841855 H 0.9508741081 6.6344397331 -3.5543692721 C -1.351521322 2.0637036677 1.9046533441 H -0.5118726264 5.7892291841 6.3192125924 C -0.5690735206 -1.6209253543 3.278317653 H 2.4850596491 -6.2957121694 4.9756186427 C -0.8902085139 -2.2984346073 -0.5338496402

C 0.9130564611 2.2509688316 -0.5312936736 2-NA4E, C1-ZEEZ, ΔG298=32.1 kJ/mol C 0.5148270446 1.5031433063 3.3308784127 0 1 C 1.4375956218 -2.0105726486 1.9919657619 C -0.0009021892 -0.0122185959 -0.0146822732 C -0.9130682988 -3.478564506 -1.320503411 C -0.0132047352 -0.0018127469 1.339205361 C 0.9380833963 3.4261061552 -1.3256350251 C -0.0345577701 -1.2801107889 -0.8177062359 C 0.2589121565 2.6415480877 4.137768705 C -0.0331387759 1.255316671 -0.8231338294 C 1.7333060106 -3.15578252 2.775794787 C 0.0325510482 -1.2656020423 2.1534465082 C 0.0343168616 -3.6248596954 -2.3854833282 C 0.0392186509 1.2654309573 2.1410404245 C 0.0117819423 3.5534959085 -2.411086425 C -1.1107403319 -2.2027354211 -0.6674338741 C -0.8389897687 3.4986379648 3.8037705238 C 1.1517097389 1.802335574 -1.3940508665 C 0.8365226994 -3.5301052191 3.8284138168 C 1.284402316 -1.9208077665 2.3335634369 C 0.9590666976 -2.5709737162 -2.6158935462 C -1.0150279627 1.5972317623 3.0411591394 C -0.8953153424 2.4866039178 -2.6539922824 C 0.940249916 -1.5590175675 -1.7597450465 C -1.632575217 3.1673405418 2.6718947333 C -1.2365453256 1.8886631482 -1.0655998832 C -0.3169745998 -2.7295865611 4.0494076404 C -1.0833589838 -1.7887402257 2.7790956263 H -1.613243525 -2.1960906023 0.2707513891 C 1.1308747945 2.1107493581 2.0684430035

11 C 0.9095390711 -2.7403666736 -2.5449741908 C 1 r21 C -1.3174353889 3.0636209118 -1.8586639937 X 1 1. 2 90. C -1.0108007861 -2.9557074498 3.5851821676 X 2 1. 1 90. 3 180. 0 C 1.2158221001 3.2952920319 2.8464689958 C 1 r51 2 a512 3 d5123 0 C -0.1716560581 -3.6633029999 -2.3727272351 C 1 r51 2 a512 3 -d5123 0 C -0.1188200388 3.601888463 -2.4282307245 C 2 r51 1 a512 4 d5123 0 C 0.2540831643 -3.6052401846 3.755226861 C 2 r51 1 a512 4 -d5123 0 C 0.1419367505 3.6230120241 3.7344917023 C 5 r95 1 a951 2 d9512 0 C -1.1757976152 -3.3519776444 -1.4187409326 C 6 r95 1 a951 2 -d9512 0 C 1.1090525466 2.9375352196 -2.1694329482 C 7 r95 2 a951 1 d9512 0 C 1.3899730308 -3.0530835372 3.1060132889 C 8 r95 2 a951 1 -d9512 0 C -0.9682295485 2.7397080206 3.803491476 C 5 r135 9 a1359 1 d13591 0 H 1.7623564314 -0.8661929916 -1.9155078009 C 6 r135 10 a1359 1 -d13591 0 H -2.1519130773 1.4836184664 -0.6409499828 C 7 r135 11 a1359 2 d13591 0 H -2.0541712963 -1.3163195844 2.6485131078 C 8 r135 12 a1359 2 -d13591 0 H 1.9553796176 1.870091044 1.4037561144 C 13 r1713 5 a17135 9 d171359 0 C 1.9181999417 -3.0381796177 -3.5016342387 C 14 r1713 6 a17135 10 -d171359 0 C -2.5505829322 3.7242614291 -2.1086025027 C 15 r1713 7 a17135 11 d171359 0 C -2.1540992318 -3.5038094199 4.2274688682 C 16 r1713 8 a17135 12 -d171359 0 C 2.3351544304 4.1678917362 2.7742808124 C 17 r2117 13 a211713 5 d2117135 0 C -0.2019975268 -4.8437634768 -3.1618502609 C 18 r2117 14 a211713 6 -d2117135 0 C -0.2002462328 4.7761452849 -3.2230951052 C 19 r2117 15 a211713 7 d2117135 0 C 0.3254831822 -4.7726387729 4.5611459812 C 20 r2117 16 a211713 8 -d2117135 0 C 0.2273645354 4.8083974452 4.511392993 C 21 r2521 17 a252117 13 d25211713 0 H -2.0086696206 -4.0393979323 -1.2895060436 C 22 r2521 18 a252117 14 -d25211713 0 H 2.0251834639 3.345694715 -2.5904033444 C 23 r2521 19 a252117 15 d25211713 0 H 2.3535201109 -3.5425550405 3.2280252594 C 24 r2521 20 a252117 16 -d25211713 0 H -1.7891579597 2.9804356299 4.475176485 H 13 r2913 5 a29135 9 d291359 0 H -1.893835243 -1.9826790558 0.0496977153 H 14 r2913 6 a29135 10 -d291359 0 H 2.106339454 1.3222904844 -1.1965674507 H 15 r2913 7 a29135 11 d291359 0 H 2.1632656638 -1.5110974403 1.8442979298 H 16 r2913 8 a29135 12 -d291359 0 H -1.874662427 0.9392107037 3.1184472672 C 17 r3317 13 a331713 5 d3317135 0 C 1.8616628168 -4.1914489198 -4.2509249863 C 18 r3317 14 a331713 6 -d3317135 0 C -2.5972579608 4.8610293187 -2.8837284249 C 19 r3317 15 a331713 7 d3317135 0 C -2.0525596941 -4.6369852869 5.0025353557 C 20 r3317 16 a331713 8 -d3317135 0 C 2.3893769315 5.3105334664 3.5404955539 C 21 r3721 17 a372117 13 d37211713 0 C 0.790936504 -5.1038390363 -4.0795974449 C 22 r3721 18 a372117 14 -d37211713 0 C -1.4107275799 5.3927060672 -3.4468543563 C 23 r3721 19 a372117 15 d37211713 0 C -0.8003585972 -5.2781250993 5.1715395914 C 24 r3721 20 a372117 16 -d37211713 0 C 1.3250900144 5.6346398318 4.4175783257 H 25 r4125 21 a412521 17 d41252117 0 H 2.7385493026 -2.33615268 -3.6328325361 H 26 r4125 22 a412521 18 -d41252117 0 H -3.4602337357 3.3149150727 -1.675370942 H 27 r4125 23 a412521 19 d41252117 0 H -3.1145856795 -3.0100293645 4.0976184931 H 28 r4125 24 a412521 20 -d41252117 0 H 3.1504481598 3.9181391483 2.0992183853 H 9 r459 5 a4595 13 d459513 0 H -1.0254409669 -5.5415940816 -3.0278919252 H 10 r459 6 a4595 14 -d459513 0 H 0.712994516 5.1816904751 -3.6526958753 H 11 r459 7 a4595 15 d459513 0 H 1.2883160229 -5.2623546962 4.6877177923 H 12 r459 8 a4595 16 -d459513 0 H -0.5915118052 5.0538668748 5.1838472605 C 33 r4933 17 a493317 13 d49331713 0 H 2.6393229803 -4.406700708 -4.9788888033 C 34 r4933 18 a493317 14 -d49331713 0 H -3.5470104467 5.356405803 -3.0669357124 C 35 r4933 19 a493317 15 d49331713 0 H -2.9346009073 -5.0446505002 5.489169536 C 36 r4933 20 a493317 16 -d49331713 0 H 3.250567474 5.970106237 3.474578805 C 37 r5337 21 a533721 25 d53372125 0 H 0.7572959906 -6.0109846152 -4.6770116364 C 38 r5337 22 a533721 26 -d53372125 0 H -1.4609372652 6.2907606473 -4.0566489092 C 39 r5337 23 a533721 27 d53372125 0 H -0.7330242743 -6.1720290283 5.7857374634 C 40 r5337 24 a533721 28 -d53372125 0 H 1.379294998 6.5395915068 5.0168014026 H 33 r5733 17 a573317 13 d57331713 0 H 34 r5733 18 a573317 14 -d57331713 0 2-NA4E, C2h-ZZZZ, ΔG298=38.95 kJ/mol H 35 r5733 19 a573317 15 d57331713 0 0 1 H 36 r5733 20 a573317 16 -d57331713 0 C H 37 r6137 21 a613721 25 d61372125 0

12 H 38 r6137 22 a613721 26 -d61372125 0 d57331713=0.12938969 H 39 r6137 23 a613721 27 d61372125 0 d61372125=0.02744841 H 40 r6137 24 a613721 28 -d61372125 0 d65493317=180.00940728 H 49 r6549 33 a654933 17 d65493317 0 d69533721=180.01757466 H 50 r6549 34 a654933 18 -d65493317 0 H 51 r6549 35 a654933 19 d65493317 0 2-NA4E, C2h-EEEE, ΔG298=39.61 kJ/mol H 52 r6549 36 a654933 20 -d65493317 0 0 1 H 53 r6953 37 a695337 21 d69533721 0 C H 54 r6953 38 a695337 22 -d69533721 0 C 1 r21 H 55 r6953 39 a695337 23 d69533721 0 X 1 1. 2 90. H 56 r6953 40 a695337 24 -d69533721 0 X 2 1. 1 90. 3 180. 0 C 1 r51 2 a512 3 d5123 0 r21=1.35224841 C 1 r51 2 a512 3 -d5123 0 r51=1.50199287 C 2 r51 1 a512 4 d5123 0 r95=1.42453844 C 2 r51 1 a512 4 -d5123 0 r135=1.38206994 C 5 r95 1 a951 2 d9512 0 r1713=1.4196295 C 6 r95 1 a951 2 -d9512 0 r2117=1.43195029 C 7 r95 2 a951 1 d9512 0 r2521=1.41992974 C 8 r95 2 a951 1 -d9512 0 r2913=1.08702149 C 5 r135 9 a1359 1 d13591 0 r3317=1.42126727 C 6 r135 10 a1359 1 -d13591 0 r3721=1.42016679 C 7 r135 11 a1359 2 d13591 0 r4125=1.08769821 C 8 r135 12 a1359 2 -d13591 0 r459=1.08576561 C 13 r1713 5 a17135 9 d171359 0 r4933=1.37667491 C 14 r1713 6 a17135 10 -d171359 0 r5337=1.37684457 C 15 r1713 7 a17135 11 d171359 0 r5733=1.08756428 C 16 r1713 8 a17135 12 -d171359 0 r6137=1.08767112 C 17 r2117 13 a211713 5 d2117135 0 r6549=1.08674626 C 18 r2117 14 a211713 6 -d2117135 0 r6953=1.0866908 C 19 r2117 15 a211713 7 d2117135 0 a512=122.23545989 C 20 r2117 16 a211713 8 -d2117135 0 a951=121.14834373 C 21 r2521 17 a252117 13 d25211713 0 a1359=118.50860016 C 22 r2521 18 a252117 14 -d25211713 0 a17135=121.84910715 C 23 r2521 19 a252117 15 d25211713 0 a211713=119.03671129 C 24 r2521 20 a252117 16 -d25211713 0 a252117=118.36658978 H 13 r2913 5 a29135 9 d291359 0 a29135=119.61200616 H 14 r2913 6 a29135 10 -d291359 0 a331713=122.17616085 H 15 r2913 7 a29135 11 d291359 0 a372117=119.03546949 H 16 r2913 8 a29135 12 -d291359 0 a412521=118.82623565 C 17 r3317 13 a331713 5 d3317135 0 a4595=119.38262364 C 18 r3317 14 a331713 6 -d3317135 0 a493317=120.8224749 C 19 r3317 15 a331713 7 d3317135 0 a533721=120.77732406 C 20 r3317 16 a331713 8 -d3317135 0 a573317=118.73798616 C 21 r3721 17 a372117 13 d37211713 0 a613721=118.75862377 C 22 r3721 18 a372117 14 -d37211713 0 a654933=120.06736302 C 23 r3721 19 a372117 15 d37211713 0 a695337=120.12447535 C 24 r3721 20 a372117 16 -d37211713 0 d5123=87.85272346 H 25 r4125 21 a412521 17 d41252117 0 d9512=110.73350482 H 26 r4125 22 a412521 18 -d41252117 0 d13591=-177.85202036 H 27 r4125 23 a412521 19 d41252117 0 d171359=-0.266909 H 28 r4125 24 a412521 20 -d41252117 0 d2117135=0.12177088 H 9 r459 5 a4595 13 d459513 0 d25211713=-0.11915003 H 10 r459 6 a4595 14 -d459513 0 d291359=179.71412374 H 11 r459 7 a4595 15 d459513 0 d3317135=-179.98069932 H 12 r459 8 a4595 16 -d459513 0 d37211713=-180.05538793 C 33 r4933 17 a493317 13 d49331713 0 d41252117=180.48413035 C 34 r4933 18 a493317 14 -d49331713 0 d459513=179.30393094 C 35 r4933 19 a493317 15 d49331713 0 d49331713=180.09201785 C 36 r4933 20 a493317 16 -d49331713 0 d53372125=180.01343831 C 37 r5337 21 a533721 25 d53372125 0

13 C 38 r5337 22 a533721 26 -d53372125 0 d25211713=-0.10727164 C 39 r5337 23 a533721 27 d53372125 0 d291359=180.30156104 C 40 r5337 24 a533721 28 -d53372125 0 d3317135=-179.55023438 H 33 r5733 17 a573317 13 d57331713 0 d37211713=-180.0852111 H 34 r5733 18 a573317 14 -d57331713 0 d41252117=179.93800979 H 35 r5733 19 a573317 15 d57331713 0 d459513=180.18093427 H 36 r5733 20 a573317 16 -d57331713 0 d49331713=180.05757856 H 37 r6137 21 a613721 25 d61372125 0 d53372125=180.11903157 H 38 r6137 22 a613721 26 -d61372125 0 d57331713=-0.04336568 H 39 r6137 23 a613721 27 d61372125 0 d61372125=0.07392611 H 40 r6137 24 a613721 28 -d61372125 0 d65493317=179.92356701 H 49 r6549 33 a654933 17 d65493317 0 d69533721=179.97901862 H 50 r6549 34 a654933 18 -d65493317 0 H 51 r6549 35 a654933 19 d65493317 0 2-NA4E, Ci-ZEZE, ΔG298=31.21 kJ/mol H 52 r6549 36 a654933 20 -d65493317 0 0 1 H 53 r6953 37 a695337 21 d69533721 0 C H 54 r6953 38 a695337 22 -d69533721 0 C 1 r21 H 55 r6953 39 a695337 23 d69533721 0 X 1 1. 2 90. H 56 r6953 40 a695337 24 -d69533721 0 X 2 1. 1 90. 3 180. 0 C 1 r51 2 a512 3 d5123 0 r21=1.35299757 C 1 r51a 2 a512a 3 -d5123 0 r51=1.50244425 C 2 r51a 1 a512a 4 d5123 0 r95=1.42481891 C 2 r51 1 a512 4 -d5123 0 r135=1.38230524 C 5 r95 1 a951 2 d9512 0 r1713=1.41978259 C 6 r95a 1 a951a 2 -d9512a 0 r2117=1.43216679 C 7 r95a 2 a951a 1 d9512a 0 r2521=1.41969317 C 8 r95 2 a951 1 -d9512 0 r2913=1.08697584 C 5 r135 9 a1359 1 d13591 0 r3317=1.4215412 C 6 r135a 10 a1359a 1 -d13591a 0 r3721=1.42039255 C 7 r135a 11 a1359a 2 d13591a 0 r4125=1.0875912 C 8 r135 12 a1359 2 -d13591 0 r459=1.08569419 C 13 r1713 5 a17135 9 d171359 0 r4933=1.3765843 C 14 r1713a 6 a17135a 10 -d171359a 0 r5337=1.37671806 C 15 r1713a 7 a17135a 11 d171359a 0 r5733=1.0877202 C 16 r1713 8 a17135 12 -d171359 0 r6137=1.0876339 C 17 r2117 13 a211713 5 d2117135 0 r6549=1.08674695 C 18 r2117a 14 a211713a 6 -d2117135a 0 r6953=1.08668487 C 19 r2117a 15 a211713a 7 d2117135a 0 a512=121.83940869 C 20 r2117 16 a211713 8 -d2117135 0 a951=119.16915076 C 21 r2521 17 a252117 13 d25211713 0 a1359=118.49416221 C 22 r2521a 18 a252117a 14 -d25211713a 0 a17135=121.79719025 C 23 r2521a 19 a252117a 15 d25211713a 0 a211713=119.06656585 C 24 r2521 20 a252117 16 -d25211713 0 a252117=118.38995589 H 13 r2913 5 a29135 9 d291359 0 a29135=120.17663422 H 14 r2913a 6 a29135a 10 -d291359a 0 a331713=122.14562225 H 15 r2913a 7 a29135a 11 d291359a 0 a372117=118.99634453 H 16 r2913 8 a29135 12 -d291359 0 a412521=118.8641043 C 17 r3317 13 a331713 5 d3317135 0 a4595=118.75195947 C 18 r3317a 14 a331713a 6 -d3317135a 0 a493317=120.84349172 C 19 r3317a 15 a331713a 7 d3317135a 0 a533721=120.81359178 C 20 r3317 16 a331713 8 -d3317135 0 a573317=118.75114543 C 21 r3721 17 a372117 13 d37211713 0 a613721=118.73904714 C 22 r3721a 18 a372117a 14 -d37211713a 0 a654933=120.06828708 C 23 r3721a 19 a372117a 15 d37211713a 0 a695337=120.13201226 C 24 r3721 20 a372117 16 -d37211713 0 d5123=92.99902471 H 25 r4125 21 a412521 17 d41252117 0 d9512=68.29820947 H 26 r4125a 22 a412521a 18 -d41252117a 0 d13591=-178.03845454 H 27 r4125a 23 a412521a 19 d41252117a 0 d171359=-0.41900174 H 28 r4125 24 a412521 20 -d41252117 0 d2117135=0.38603087 H 9 r459 5 a4595 13 d459513 0

14 H 10 r459a 6 a4595a 14 -d459513a 0 r6549a=1.0867129 H 11 r459a 7 a4595a 15 d459513a 0 r6953=1.08663907 H 12 r459 8 a4595 16 -d459513 0 r6953a=1.08670646 C 33 r4933 17 a493317 13 d49331713 0 a512=122.31315439 C 34 r4933a 18 a493317a 14 -d49331713a 0 a512a=123.19625303 C 35 r4933a 19 a493317a 15 d49331713a 0 a951=118.61472425 C 36 r4933 20 a493317 16 -d49331713 0 a951a=119.96592483 C 37 r5337 21 a533721 25 d53372125 0 a1359=118.60417921 C 38 r5337a 22 a533721a 26 -d53372125a 0 a1359a=118.28272697 C 39 r5337a 23 a533721a 27 d53372125a 0 a17135=121.77131136 C 40 r5337 24 a533721 28 -d53372125 0 a17135a=121.90818464 H 33 r5733 17 a573317 13 d57331713 0 a211713=119.00968277 H 34 r5733a 18 a573317a 14 -d57331713a 0 a211713a=119.11764547 H 35 r5733a 19 a573317a 15 d57331713a 0 a252117=118.42663681 H 36 r5733 20 a573317 16 -d57331713 0 a252117a=118.28816521 H 37 r6137 21 a613721 25 d61372125 0 a29135=120.04690577 H 38 r6137a 22 a613721a 26 -d61372125a 0 a29135a=119.74736657 H 39 r6137a 23 a613721a 27 d61372125a 0 a331713=122.19603479 H 40 r6137 24 a613721 28 -d61372125 0 a331713a=122.08094475 H 49 r6549 33 a654933 17 d65493317 0 a372117=118.99484849 H 50 r6549a 34 a654933a 18 -d65493317a 0 a372117a=119.04139049 H 51 r6549a 35 a654933a 19 d65493317a 0 a412521=118.83120381 H 52 r6549 36 a654933 20 -d65493317 0 a412521a=118.83858258 H 53 r6953 37 a695337 21 d69533721 0 a4595=118.74760539 H 54 r6953a 38 a695337a 22 -d69533721a 0 a4595a=119.23617548 H 55 r6953a 39 a695337a 23 d69533721a 0 a493317=120.84151748 H 56 r6953 40 a695337 24 -d69533721 0 a493317a=120.81952834 a533721=120.81866145 r21=1.35449819 a533721a=120.77056276 r51=1.5045085 a573317=118.7725378 r51a=1.49994046 a573317a=118.73745565 r95=1.42422343 a613721=118.7219741 r95a=1.42623135 a613721a=118.77912252 r135=1.38166611 a654933=120.05885604 r135a=1.38282319 a654933a=120.06333962 r1713=1.42060163 a695337=120.13240232 r1713a=1.41986314 a695337a=120.11890322 r2117=1.43201561 d5123=92.2025586 r2117a=1.43156857 d9512=84.30458067 r2521=1.42018056 d9512a=-123.62114676 r2521a=1.42043087 d13591=-177.16514691 r2913=1.08775488 d13591a=-182.7652418 r2913a=1.08535082 d171359=-0.41233765 r3317=1.42117672 d171359a=1.09317075 r3317a=1.42119925 d2117135=-0.00936639 r3721=1.42030377 d2117135a=-0.19562759 r3721a=1.41975381 d25211713=0.19729381 r4125=1.087621 d25211713a=-0.34703584 r4125a=1.08766015 d291359=180.43249633 r459=1.08628316 d291359a=181.44145991 r459a=1.08529665 d3317135=-179.70784754 r4933=1.37676716 d3317135a=-180.11774466 r4933a=1.37687158 d37211713=-179.77048189 r5337=1.37681414 d37211713a=-180.07004507 r5337a=1.37717526 d41252117=180.0270389 r5733=1.08779609 d41252117a=180.20313478 r5733a=1.08751125 d459513=180.39332929 r6137=1.08760549 d459513a=178.79561825 r6137a=1.0876652 d49331713=179.74428754 r6549=1.08673076 d49331713a=180.08502072

15 d53372125=180.08485178 H 12 r459 8 a4595 16 -d459513 0 d53372125a=180.34457731 C 33 r4933 17 a493317 13 d49331713 0 d57331713=-0.35644452 C 34 r4933 18 a493317 14 -d49331713 0 d57331713a=-0.16049303 C 35 r4933 19 a493317 15 d49331713 0 d61372125=0.05646391 C 36 r4933 20 a493317 16 -d49331713 0 d61372125a=0.32656368 C 37 r5337 21 a533721 25 d53372125 0 d65493317=179.9734078 C 38 r5337 22 a533721 26 -d53372125 0 d65493317a=179.84110741 C 39 r5337 23 a533721 27 d53372125 0 d69533721=179.96685624 C 40 r5337 24 a533721 28 -d53372125 0 d69533721a=180.02779548 H 33 r5733 17 a573317 13 d57331713 0 H 34 r5733 18 a573317 14 -d57331713 0 2-NA4E, C2v-ZZZZ, ΔG298=42.33 kJ/mol H 35 r5733 19 a573317 15 d57331713 0 0 1 H 36 r5733 20 a573317 16 -d57331713 0 C H 37 r6137 21 a613721 25 d61372125 0 C 1 r21 H 38 r6137 22 a613721 26 -d61372125 0 X 1 1. 2 90. H 39 r6137 23 a613721 27 d61372125 0 X 2 1. 1 90. 3 0. 0 H 40 r6137 24 a613721 28 -d61372125 0 C 1 r51 2 a512 3 d5123 0 H 49 r6549 33 a654933 17 d65493317 0 C 1 r51 2 a512 3 -d5123 0 H 50 r6549 34 a654933 18 -d65493317 0 C 2 r51 1 a512 4 d5123 0 H 51 r6549 35 a654933 19 d65493317 0 C 2 r51 1 a512 4 -d5123 0 H 52 r6549 36 a654933 20 -d65493317 0 C 5 r95 1 a951 2 d9512 0 H 53 r6953 37 a695337 21 d69533721 0 C 6 r95 1 a951 2 -d9512 0 H 54 r6953 38 a695337 22 -d69533721 0 C 7 r95 2 a951 1 d9512 0 H 55 r6953 39 a695337 23 d69533721 0 C 8 r95 2 a951 1 -d9512 0 H 56 r6953 40 a695337 24 -d69533721 0 C 5 r135 9 a1359 1 d13591 0 C 6 r135 10 a1359 1 -d13591 0 r21=1.34834733 C 7 r135 11 a1359 2 d13591 0 r51=1.50224009 C 8 r135 12 a1359 2 -d13591 0 r95=1.42364771 C 13 r1713 5 a17135 9 d171359 0 r135=1.38105175 C 14 r1713 6 a17135 10 -d171359 0 r1713=1.41985952 C 15 r1713 7 a17135 11 d171359 0 r2117=1.4323225 C 16 r1713 8 a17135 12 -d171359 0 r2521=1.41995938 C 17 r2117 13 a211713 5 d2117135 0 r2913=1.08749062 C 18 r2117 14 a211713 6 -d2117135 0 r3317=1.42123007 C 19 r2117 15 a211713 7 d2117135 0 r3721=1.42050134 C 20 r2117 16 a211713 8 -d2117135 0 r4125=1.08767621 C 21 r2521 17 a252117 13 d25211713 0 r459=1.08644747 C 22 r2521 18 a252117 14 -d25211713 0 r4933=1.37658129 C 23 r2521 19 a252117 15 d25211713 0 r5337=1.37668592 C 24 r2521 20 a252117 16 -d25211713 0 r5733=1.08764244 H 13 r2913 5 a29135 9 d291359 0 r6137=1.08767511 H 14 r2913 6 a29135 10 -d291359 0 r6549=1.08674036 H 15 r2913 7 a29135 11 d291359 0 r6953=1.08669016 H 16 r2913 8 a29135 12 -d291359 0 a512=122.4715412 C 17 r3317 13 a331713 5 d3317135 0 a951=120.07469314 C 18 r3317 14 a331713 6 -d3317135 0 a1359=118.74233738 C 19 r3317 15 a331713 7 d3317135 0 a17135=121.7100237 C 20 r3317 16 a331713 8 -d3317135 0 a211713=119.01451002 C 21 r3721 17 a372117 13 d37211713 0 a252117=118.44774041 C 22 r3721 18 a372117 14 -d37211713 0 a29135=119.77759862 C 23 r3721 19 a372117 15 d37211713 0 a331713=122.1915072 C 24 r3721 20 a372117 16 -d37211713 0 a372117=118.99118115 H 25 r4125 21 a412521 17 d41252117 0 a412521=118.82718314 H 26 r4125 22 a412521 18 -d41252117 0 a4595=119.08320277 H 27 r4125 23 a412521 19 d41252117 0 a493317=120.8413378 H 28 r4125 24 a412521 20 -d41252117 0 a533721=120.80683012 H 9 r459 5 a4595 13 d459513 0 a573317=118.7354352 H 10 r459 6 a4595 14 -d459513 0 a613721=118.73797265 H 11 r459 7 a4595 15 d459513 0 a654933=120.06964071

16 a695337=120.12645514 C 24 r3721a 20 a372117a 16 -d37211713a 0 d5123=90.60777496 H 25 r4125 21 a412521 17 d41252117 0 d9512=94.29087296 H 26 r4125 22 a412521 18 -d41252117 0 d13591=-177.77728335 C 27 r4125a 23 a412521a 19 d41252117a 0 d171359=-0.42418793 C 28 r4125a 24 a412521a 20 -d41252117a 0 d2117135=0.25872847 H 9 r459 5 a4595 13 d459513 0 d25211713=-0.07188168 H 10 r459 6 a4595 14 -d459513 0 d291359=179.65947656 H 11 r459a 7 a4595a 15 d459513a 0 d3317135=-179.73060163 H 12 r459a 8 a4595a 16 -d459513a 0 d37211713=-179.98492079 C 33 r4933 17 a493317 13 d49331713 0 d41252117=180.26145095 C 34 r4933 18 a493317 14 -d49331713 0 d459513=179.83559238 C 39 r4933a 23 a493317a 19 d49331713a 0 d49331713=179.98822868 C 40 r4933a 24 a493317a 20 -d49331713a 0 d53372125=180.08263945 C 37 r5337 21 a533721 25 d53372125 0 d57331713=-0.00062176 C 38 r5337 22 a533721 26 -d53372125 0 d61372125=0.05955056 C 43 r5337a 27 a533721a 11 d53372125a 0 d65493317=180.00916834 C 44 r5337a 28 a533721a 12 -d53372125a 0 d69533721=179.99590968 H 33 r5733 17 a573317 13 d57331713 0 H 34 r5733 18 a573317 14 -d57331713 0 2-NA4E, Cs-ZZEE, ΔG298=37.01 kJ/mol H 39 r5733a 23 a573317a 19 d57331713a 0 0 1 H 40 r5733a 24 a573317a 20 -d57331713a 0 C H 37 r6137 21 a613721 25 d61372125 0 C 1 r21 H 38 r6137 22 a613721 26 -d61372125 0 X 1 1. 2 90. H 43 r6137a 27 a613721a 11 d61372125a 0 X 2 1. 1 90. 3 180. 0 H 44 r6137a 28 a613721a 12 -d61372125a 0 C 1 r51 2 a512 3 d5123 0 H 49 r6549 33 a654933 17 d65493317 0 C 1 r51 2 a512 3 -d5123 0 H 50 r6549 34 a654933 18 -d65493317 0 C 2 r51a 1 a512a 4 d5123a 0 H 51 r6549a 39 a654933a 23 d65493317a 0 C 2 r51a 1 a512a 4 -d5123a 0 H 52 r6549a 40 a654933a 24 -d65493317a 0 C 5 r95 1 a951 2 d9512 0 H 53 r6953 37 a695337 21 d69533721 0 C 6 r95 1 a951 2 -d9512 0 H 54 r6953 38 a695337 22 -d69533721 0 C 7 r95a 2 a951a 1 d9512a 0 H 55 r6953a 43 a695337a 27 d69533721a 0 C 8 r95a 2 a951a 1 -d9512a 0 H 56 r6953a 44 a695337a 28 -d69533721a 0 C 5 r135 9 a1359 1 d13591 0 C 6 r135 10 a1359 1 -d13591 0 r21=1.35219314 C 7 r135a 11 a1359a 2 d13591a 0 r51=1.50196903 C 8 r135a 12 a1359a 2 -d13591a 0 r51a=1.50292068 C 13 r1713 5 a17135 9 d171359 0 r95=1.4246851 C 14 r1713 6 a17135 10 -d171359 0 r95a=1.38205065 C 15 r1713a 7 a17135a 11 d171359a 0 r135=1.38212476 C 16 r1713a 8 a17135a 12 -d171359a 0 r135a=1.42450977 C 17 r2117 13 a211713 5 d2117135 0 r1713=1.41945521 C 18 r2117 14 a211713 6 -d2117135 0 r1713a=1.37482795 C 19 r2117a 15 a211713a 7 d2117135a 0 r2117=1.43207434 C 20 r2117a 16 a211713a 8 -d2117135a 0 r2117a=1.41966535 C 21 r2521 17 a252117 13 d25211713 0 r2521=1.41996311 C 22 r2521 18 a252117 14 -d25211713 0 r2521a=1.4323019 C 23 r2521a 19 a252117a 15 d25211713a 0 r2913=1.08689795 C 24 r2521a 20 a252117a 16 -d25211713a 0 r2913a=1.08590379 H 13 r2913 5 a29135 9 d291359 0 r3317=1.421203 H 14 r2913 6 a29135 10 -d291359 0 r3317a=1.08761684 H 15 r2913a 7 a29135a 11 d291359a 0 r3721=1.42024369 H 16 r2913a 8 a29135a 12 -d291359a 0 r3721a=1.42044214 C 17 r3317 13 a331713 5 d3317135 0 r4125=1.08768309 C 18 r3317 14 a331713 6 -d3317135 0 r4125a=1.42151118 H 19 r3317a 15 a331713a 7 d3317135a 0 r459=1.0858711 H 20 r3317a 16 a331713a 8 -d3317135a 0 r459a=1.0870063 C 21 r3721 17 a372117 13 d37211713 0 r4933=1.37665317 C 22 r3721 18 a372117 14 -d37211713 0 r4933a=1.37672151 C 23 r3721a 19 a372117a 15 d37211713a 0 r5337=1.37688775

17 r5337a=1.37650421 d37211713a=-179.9158312 r5733=1.08751068 d41252117=180.51303719 r5733a=1.08763545 d41252117a=180.20007572 r6137=1.08767526 d459513=179.23594905 r6137a=1.08770192 d459513a=179.66631164 r6549=1.08671748 d49331713=180.12143536 r6549a=1.0866841 d49331713a=179.86305878 r6953=1.08670343 d53372125=179.99339537 r6953a=1.0867427 d53372125a=179.89050106 a512=122.24860695 d57331713=0.1846609 a512a=121.99847667 d57331713a=-0.0751458 a951=121.2229724 d61372125=0.02504275 a951a=122.13374922 d61372125a=0.00507535 a1359=118.53191153 d65493317=180.01513755 a1359a=118.52669669 d65493317a=180.02454839 a17135=121.84056669 d69533721=180.03259078 a17135a=121.19931673 d69533721a=180.07463969 a211713=119.03734757 a211713a=121.03395201 2-NA4E, Cs-ZZZZ, ΔG298=36.89 kJ/mol a252117=118.37503533 0 1 a252117a=118.37983059 C a29135=119.57906163 C 1 r21 a29135a=118.75804126 X 1 1. 2 90. a331713=122.14746973 X 2 1. 1 90. 3 0. 0 a331713a=120.10722012 C 1 r51 2 a512 3 d5123 0 a372117=119.01589514 C 1 r51a 2 a512a 3 -d5123 0 a372117a=122.62408082 C 2 r51a 1 a512a 4 d5123 0 a412521=118.82804444 C 2 r51 1 a512 4 -d5123 0 a412521a=118.78586921 C 5 r95 1 a951 2 d9512 0 a4595=119.39231986 C 6 r95a 1 a951a 2 -d9512a 0 a4595a=120.16554859 C 7 r95a 2 a951a 1 d9512a 0 a493317=120.81005341 C 8 r95 2 a951 1 -d9512 0 a493317a=120.80906231 C 5 r135 9 a1359 1 d13591 0 a533721=120.76875483 C 6 r135a 10 a1359a 1 -d13591a 0 a533721a=120.84639225 C 7 r135a 11 a1359a 2 d13591a 0 a573317=118.73708904 C 8 r135 12 a1359 2 -d13591 0 a573317a=118.72383262 C 13 r1713 5 a17135 9 d171359 0 a613721=118.77315983 C 14 r1713a 6 a17135a 10 -d171359a 0 a613721a=118.74638871 C 15 r1713a 7 a17135a 11 d171359a 0 a654933=120.07230325 C 16 r1713 8 a17135 12 -d171359 0 a654933a=120.12611407 C 17 r2117 13 a211713 5 d2117135 0 a695337=120.11700581 C 18 r2117a 14 a211713a 6 -d2117135a 0 a695337a=120.07387979 C 19 r2117a 15 a211713a 7 d2117135a 0 d5123=87.77372388 C 20 r2117 16 a211713 8 -d2117135 0 d5123a=87.34128049 C 21 r2521 17 a252117 13 d25211713 0 d9512=110.68700083 C 22 r2521a 18 a252117a 14 -d25211713a 0 d9512a=112.21441336 C 23 r2521a 19 a252117a 15 d25211713a 0 d13591=-177.7831668 C 24 r2521 20 a252117 16 -d25211713 0 d13591a=-177.79122589 H 13 r2913 5 a29135 9 d291359 0 d171359=-0.13132355 H 14 r2913a 6 a29135a 10 -d291359a 0 d171359a=-0.1804403 H 15 r2913a 7 a29135a 11 d291359a 0 d2117135=0.03671637 H 16 r2913 8 a29135 12 -d291359 0 d2117135a=-0.04236561 C 17 r3317 13 a331713 5 d3317135 0 d25211713=-0.13687625 C 18 r3317a 14 a331713a 6 -d3317135a 0 d25211713a=0.03551295 C 19 r3317a 15 a331713a 7 d3317135a 0 d291359=179.80862944 C 20 r3317 16 a331713 8 -d3317135 0 d291359a=179.78990877 C 21 r3721 17 a372117 13 d37211713 0 d3317135=-180.08790097 C 22 r3721a 18 a372117a 14 -d37211713a 0 d3317135a=-179.99763874 C 23 r3721a 19 a372117a 15 d37211713a 0 d37211713=-180.06995252 C 24 r3721 20 a372117 16 -d37211713 0

18 H 25 r4125 21 a412521 17 d41252117 0 r5733=1.08768227 H 26 r4125a 22 a412521a 18 -d41252117a 0 r5733a=1.08768199 H 27 r4125a 23 a412521a 19 d41252117a 0 r6137=1.0876399 H 28 r4125 24 a412521 20 -d41252117 0 r6137a=1.08763998 H 9 r459 5 a4595 13 d459513 0 r6549=1.08673906 H 10 r459a 6 a4595a 14 -d459513a 0 r6549a=1.08673898 H 11 r459a 7 a4595a 15 d459513a 0 r6953=1.08668559 H 12 r459 8 a4595 16 -d459513 0 r6953a=1.08668559 C 33 r4933 17 a493317 13 d49331713 0 a512=123.28786046 C 34 r4933a 18 a493317a 14 -d49331713a 0 a512a=123.30166672 C 35 r4933a 19 a493317a 15 d49331713a 0 a951=118.81031963 C 36 r4933 20 a493317 16 -d49331713 0 a951a=118.80055802 C 37 r5337 21 a533721 25 d53372125 0 a1359=118.61640792 C 38 r5337a 22 a533721a 26 -d53372125a 0 a1359a=118.61429952 C 39 r5337a 23 a533721a 27 d53372125a 0 a17135=121.72973344 C 40 r5337 24 a533721 28 -d53372125 0 a17135a=121.72977217 H 33 r5733 17 a573317 13 d57331713 0 a211713=119.04644354 H 34 r5733a 18 a573317a 14 -d57331713a 0 a211713a=119.04777122 H 35 r5733a 19 a573317a 15 d57331713a 0 a252117=118.42625847 H 36 r5733 20 a573317 16 -d57331713 0 a252117a=118.42565316 H 37 r6137 21 a613721 25 d61372125 0 a29135=119.89800486 H 38 r6137a 22 a613721a 26 -d61372125a 0 a29135a=119.90191445 H 39 r6137a 23 a613721a 27 d61372125a 0 a331713=122.15160005 H 40 r6137 24 a613721 28 -d61372125 0 a331713a=122.15022385 H 49 r6549 33 a654933 17 d65493317 0 a372117=119.00615133 H 50 r6549a 34 a654933a 18 -d65493317a 0 a372117a=119.00638444 H 51 r6549a 35 a654933a 19 d65493317a 0 a412521=118.8337286 H 52 r6549 36 a654933 20 -d65493317 0 a412521a=118.83386157 H 53 r6953 37 a695337 21 d69533721 0 a4595=118.87425736 H 54 r6953a 38 a695337a 22 -d69533721a 0 a4595a=118.87311716 H 55 r6953a 39 a695337a 23 d69533721a 0 a493317=120.84169037 H 56 r6953 40 a695337 24 -d69533721 0 a493317a=120.84167417 a533721=120.8021719 r21=1.35181167 a533721a=120.80197053 r51=1.50179565 a573317=118.76674162 r51a=1.50181223 a573317a=118.76649589 r95=1.4250468 a613721=118.74507776 r95a=1.42506376 a613721a=118.74523742 r135=1.38116868 a654933=120.07351298 r135a=1.38117072 a654933a=120.07371681 r1713=1.42082412 a695337=120.1260249 r1713a=1.42083149 a695337a=120.12599623 r2117=1.43183019 d5123=89.99598626 r2117a=1.43182389 d9512=106.44171908 r2521=1.42077472 d9512a=-106.41071235 r2521a=1.42077249 d13591=-176.75949713 r2913=1.08657144 d13591a=-183.24441902 r2913a=1.08657802 d171359=-0.94259108 r3317=1.42087615 d171359a=0.93354999 r3317a=1.42087403 d2117135=0.05881405 r3721=1.41996561 d2117135a=-0.05239392 r3721a=1.41996536 d25211713=0.40743552 r4125=1.08764185 d25211713a=-0.40853944 r4125a=1.08764227 d291359=178.76595704 r459=1.08644311 d291359a=181.23937018 r459a=1.08644194 d3317135=-179.91818607 r4933=1.37692657 d3317135a=-180.07883977 r4933a=1.37692762 d37211713=-179.84609576 r5337=1.37708474 d37211713a=-180.15855445 r5337a=1.37708491 d41252117=179.80040555

19 d41252117a=180.19883765 H 23 r3721 19 a372117 15 d37211713 0 d459513=181.12606458 H 24 r3721 20 a372117 16 d37211713 0 d459513a=178.88930729 H 25 r4125 21 a412521 17 d41252117 0 d49331713=179.87789071 H 26 r4125 22 a412521 18 d41252117 0 d49331713a=180.12632333 H 27 r4125 23 a412521 19 d41252117 0 d53372125=179.65689378 H 28 r4125 24 a412521 20 d41252117 0 d53372125a=180.34100982 H 9 r459 5 a4595 13 d459513 0 d57331713=-0.06083031 H 10 r459 6 a4595 14 d459513 0 d57331713a=0.06404735 H 11 r459 7 a4595 15 d459513 0 d61372125=-0.31547296 H 12 r459 8 a4595 16 d459513 0 d61372125a=0.31188846 d65493317=180.04177516 r21=1.36618383 d65493317a=179.95778474 r51=1.4953625 d69533721=179.99286549 r95=1.40613173 d69533721a=180.00514272 r135=1.40522286 r1713=1.39409689 Coordinates of the optimized r2117=1.39621722 r2521=1.39651002 conformations of 2-NA4E. r2913=1.08551586 r3317=1.08696486 Ph4E, D2, ΔG298=1.73 kJ/mol r3721=1.08680576 0 1 r4125=1.08702659 C r459=3.21306484 C 1 r21 a512=122.68962016 X 1 1. 2 90. a951=120.46730132 X 2 1. 1 90. 3 d4213 0 a1359=118.14126123 C 1 r51 2 a512 3 90. 0 a17135=120.91102836 C 1 r51 2 a512 3 -90. 0 a211713=120.27768014 C 2 r51 1 a512 4 90. 0 a252117=119.48800916 C 2 r51 1 a512 4 -90. 0 a29135=119.20605699 C 5 r95 1 a951 2 d9512 0 a331713=119.604671 C 6 r95 1 a951 2 d9512 0 a372117=120.25555155 C 7 r95 2 a951 1 d9512 0 a412521=120.11741531 C 8 r95 2 a951 1 d9512 0 a4595=59.80021185 C 5 r135 9 a1359 1 d13591 0 d4213=168.0119894 C 6 r135 10 a1359 1 d13591 0 d9512=-227.13239174 C 7 r135 11 a1359 2 d13591 0 d13591=-177.30178205 C 8 r135 12 a1359 2 d13591 0 d171359=-0.97808667 C 13 r1713 5 a17135 9 d171359 0 d2117135=-0.07439285 C 14 r1713 6 a17135 10 d171359 0 d25211713=0.55578503 C 15 r1713 7 a17135 11 d171359 0 d291359=178.9315201 C 16 r1713 8 a17135 12 d171359 0 d3317135=-180.29960912 C 17 r2117 13 a211713 5 d2117135 0 d37211713=-179.88856228 C 18 r2117 14 a211713 6 d2117135 0 d41252117=179.72150639 C 19 r2117 15 a211713 7 d2117135 0 d459513=254.01453079 C 20 r2117 16 a211713 8 d2117135 0

C 21 r2521 17 a252117 13 d25211713 0 Ph4E, C2, ΔG298=1.06 kJ/mol C 22 r2521 18 a252117 14 d25211713 0 0 1 C 23 r2521 19 a252117 15 d25211713 0 C C 24 r2521 20 a252117 16 d25211713 0 C 1 r21 H 13 r2913 5 a29135 9 d291359 0 X 1 1. 2 90. H 14 r2913 6 a29135 10 d291359 0 X 2 1. 1 90. 3 d4213 0 H 15 r2913 7 a29135 11 d291359 0 C 1 r51 2 a512 3 90. 0 H 16 r2913 8 a29135 12 d291359 0 C 1 r51 2 a512 3 -90. 0 H 17 r3317 13 a331713 5 d3317135 0 C 2 r51a 1 a512a 4 90. 0 H 18 r3317 14 a331713 6 d3317135 0 C 2 r51a 1 a512a 4 -90. 0 H 19 r3317 15 a331713 7 d3317135 0 C 5 r95 1 a951 2 d9512 0 H 20 r3317 16 a331713 8 d3317135 0 C 6 r95 1 a951 2 d9512 0 H 21 r3721 17 a372117 13 d37211713 0 C 7 r95a 2 a951a 1 d9512a 0 H 22 r3721 18 a372117 14 d37211713 0 C 8 r95a 2 a951a 1 d9512a 0

20 C 5 r135 9 a1359 1 d13591 0 C 6 r135 10 a1359 1 d13591 0 r21=1.36610167 C 7 r135a 11 a1359a 2 d13591a 0 r51=1.49539516 C 8 r135a 12 a1359a 2 d13591a 0 r51a=1.49530455 C 13 r1713 5 a17135 9 d171359 0 r95=1.40619569 C 14 r1713 6 a17135 10 d171359 0 r95a=1.40614187 C 15 r1713a 7 a17135a 11 d171359a 0 r135=1.40521086 C 16 r1713a 8 a17135a 12 d171359a 0 r135a=1.40522882 C 17 r2117 13 a211713 5 d2117135 0 r1713=1.39407897 C 18 r2117 14 a211713 6 d2117135 0 r1713a=1.39404044 C 19 r2117a 15 a211713a 7 d2117135a 0 r2117=1.3961636 C 20 r2117a 16 a211713a 8 d2117135a 0 r2117a=1.39620836 C 21 r2521 17 a252117 13 d25211713 0 r2521=1.39649191 C 22 r2521 18 a252117 14 d25211713 0 r2521a=1.3964446 C 23 r2521a 19 a252117a 15 d25211713a 0 r2913=1.08553666 C 24 r2521a 20 a252117a 16 d25211713a 0 r2913a=1.08555386 H 13 r2913 5 a29135 9 d291359 0 r3317=1.0869632 H 14 r2913 6 a29135 10 d291359 0 r3317a=1.08696642 H 15 r2913a 7 a29135a 11 d291359a 0 r3721=1.08682349 H 16 r2913a 8 a29135a 12 d291359a 0 r3721a=1.08681523 H 17 r3317 13 a331713 5 d3317135 0 r4125=1.08703161 H 18 r3317 14 a331713 6 d3317135 0 r4125a=1.08703785 H 19 r3317a 15 a331713a 7 d3317135a 0 r459=1.08641818 H 20 r3317a 16 a331713a 8 d3317135a 0 r459a=1.08648882 H 21 r3721 17 a372117 13 d37211713 0 a512=122.69494426 H 22 r3721 18 a372117 14 d37211713 0 a512a=122.68059556 H 23 r3721a 19 a372117a 15 d37211713a 0 a951=120.48946378 H 24 r3721a 20 a372117a 16 d37211713a 0 a951a=120.49458355 H 25 r4125 21 a412521 17 d41252117 0 a1359=118.13431473 H 26 r4125 22 a412521 18 d41252117 0 a1359a=118.13829411 H 27 r4125a 11 a412521a 7 d41252117a 0 a17135=120.92448253 H 28 r4125a 12 a412521a 8 d41252117a 0 a17135a=120.92002633 H 9 r459 5 a4595 13 d459513 0 a211713=120.26883069 H 10 r459 6 a4595 14 d459513 0 a211713a=120.27312739 H 11 r459a 7 a4595a 15 d459513a 0 a252117=119.48900098 H 12 r459a 8 a4595a 16 d459513a 0 a252117a=119.48753764 X 33 r4933 17 a493317 13 d49331713 0 a29135=119.22100769 X 34 r4933 18 a493317 14 d49331713 0 a29135a=119.22409882 X 39 r4933a 23 a493317a 19 d49331713a 0 a331713=119.60689782 X 40 r4933a 24 a493317a 20 d49331713a 0 a331713a=119.6077455 X 37 r5337 21 a533721 25 d53372125 0 a372117=120.26176296 X 38 r5337 22 a533721 26 d53372125 0 a372117a=120.25713537 X 43 r5337a 27 a533721a 11 d53372125a 0 a412521=120.11381059 X 44 r5337a 28 a533721a 12 d53372125a 0 a412521a=119.66775138 X 33 r5733 17 a573317 13 d57331713 0 a4595=119.24340482 X 34 r5733 18 a573317 14 d57331713 0 a4595a=119.25804245 X 39 r5733a 23 a573317a 19 d57331713a 0 d4213=168.05421285 X 40 r5733a 24 a573317a 20 d57331713a 0 d9512=-227.04529071 X 37 r6137 21 a613721 25 d61372125 0 d9512a=-227.25011836 X 38 r6137 22 a613721 26 d61372125 0 d13591=-177.21815803 X 43 r6137a 27 a613721a 11 d61372125a 0 d13591a=-177.35123306 X 44 r6137a 28 a613721a 12 d61372125a 0 d171359=-0.9700429 X 49 r6549 33 a654933 17 d65493317 0 d171359a=-1.01516163 X 50 r6549 34 a654933 18 d65493317 0 d2117135=-0.07452178 X 51 r6549a 39 a654933a 23 d65493317a 0 d2117135a=-0.07745615 X 52 r6549a 40 a654933a 24 d65493317a 0 d25211713=0.55676975 X 53 r6953 37 a695337 21 d69533721 0 d25211713a=0.58478106 X 54 r6953 38 a695337 22 d69533721 0 d291359=178.90979094 X 55 r6953a 43 a695337a 27 d69533721a 0 d291359a=178.93017468 X 56 r6953a 44 a695337a 28 d69533721a 0 d3317135=-180.30392613

21 d3317135a=-180.28289226 C 7 r135 11 a1359 2 d13591 0 d37211713=-179.8945626 C 8 r135a 12 a1359a 2 d13591a 0 d37211713a=-179.86202852 C 13 r1713 5 a17135 9 d171359 0 d41252117=179.70610439 C 14 r1713a 6 a17135a 10 d171359a 0 d41252117a=179.15505691 C 15 r1713 7 a17135 11 d171359 0 d459513=-178.70039224 C 16 r1713a 8 a17135a 12 d171359a 0 d459513a=-178.70010981 C 17 r2117 13 a211713 5 d2117135 0 r4933=1.37672185 C 18 r2117a 14 a211713a 6 d2117135a 0 r4933a=1.37742524 C 19 r2117 15 a211713 7 d2117135 0 r5337=1.37742172 C 20 r2117a 16 a211713a 8 d2117135a 0 r5337a=1.37672558 C 21 r2521 17 a252117 13 d25211713 0 r5733=1.08745214 C 22 r2521a 18 a252117a 14 d25211713a 0 r5733a=1.08765239 C 23 r2521 19 a252117 15 d25211713 0 r6137=1.08768138 C 24 r2521a 20 a252117a 16 d25211713a 0 r6137a=1.08758513 H 13 r2913 5 a29135 9 d291359 0 r6549=1.08669352 H 14 r2913a 6 a29135a 10 d291359a 0 r6549a=1.0867367 H 15 r2913 7 a29135 11 d291359 0 r6953=1.08672599 H 16 r2913a 8 a29135a 12 d291359a 0 r6953a=1.08673931 H 17 r3317 13 a331713 5 d3317135 0 a493317=120.81324895 H 22 r3317a 18 a331713a 14 d3317135a 0 a493317a=120.78562971 H 19 r3317 15 a331713 7 d3317135 0 a533721=120.78059979 H 24 r3317a 20 a331713a 16 d3317135a 0 a533721a=120.81241504 H 21 r3721 17 a372117 13 d37211713 0 a573317=118.71479085 H 26 r3721a 10 a372117a 6 d37211713a 0 a573317a=118.76083036 H 23 r3721 19 a372117 15 d37211713 0 a613721=118.76606013 H 28 r3721a 12 a372117a 8 d37211713a 0 a613721a=118.71367034 H 25 r4125 21 a412521 17 d41252117 0 a654933=120.07493408 H 18 r4125a 14 a412521a 6 d41252117a 0 a654933a=120.10452089 H 27 r4125 23 a412521 19 d41252117 0 a695337=120.09261219 H 20 r4125a 16 a412521a 8 d41252117a 0 a695337a=120.08440264 H 9 r459 5 a4595 13 d459513 0 d49331713=179.87557783 H 10 r459a 6 a4595a 14 d459513a 0 d49331713a=180.25906701 H 11 r459 7 a4595 15 d459513 0 d53372125=179.59154424 H 12 r459a 8 a4595a 16 d459513a 0 d53372125a=179.82631329 X 33 r4933 17 a493317 13 d49331713 0 d57331713=0.16470425 X 34 r4933a 22 a493317a 18 d49331713a 0 d57331713a=0.3488129 X 35 r4933 19 a493317 15 d49331713 0 d61372125=-0.36448057 X 36 r4933a 24 a493317a 20 d49331713a 0 d61372125a=-0.10984018 X 37 r5337 21 a533721 25 d53372125 0 d65493317=180.17885095 X 38 r5337a 26 a533721a 10 d53372125a 0 d65493317a=180.10750358 X 39 r5337 23 a533721 27 d53372125 0 d69533721=179.98668105 X 40 r5337a 28 a533721a 12 d53372125a 0 d69533721a=180.0120301 X 33 r5733 17 a573317 13 d57331713 0 X 34 r5733a 22 a573317a 18 d57331713a 0

Ph4E, C2, ΔG298=0.01 kJ/mol X 35 r5733 19 a573317 15 d57331713 0 0 1 X 36 r5733a 24 a573317a 20 d57331713a 0 C X 37 r6137 21 a613721 25 d61372125 0 C 1 r21 X 38 r6137a 26 a613721a 10 d61372125a 0 X 1 1. 2 90. X 39 r6137 23 a613721 27 d61372125 0 X 2 1. 1 90. 3 d4213 0 X 40 r6137a 28 a613721a 12 d61372125a 0 C 1 r51 2 a512 3 d5123 0 X 49 r6549 33 a654933 17 d65493317 0 C 1 r51a 2 a512a 3 -d5123 0 X 50 r6549a 34 a654933a 18 d65493317a 0 C 2 r51 1 a512 4 d5123 0 X 51 r6549 35 a654933 19 d65493317 0 C 2 r51a 1 a512a 4 -d5123 0 X 52 r6549a 36 a654933a 20 d65493317a 0 C 5 r95 1 a951 2 d9512 0 X 53 r6953 37 a695337 21 d69533721 0 C 6 r95a 1 a951a 2 d9512a 0 X 54 r6953a 38 a695337a 22 d69533721a 0 C 7 r95 2 a951 1 d9512 0 X 55 r6953 39 a695337 23 d69533721 0 C 8 r95a 2 a951a 1 d9512a 0 X 56 r6953a 40 a695337a 24 d69533721a 0 C 5 r135 9 a1359 1 d13591 0 C 6 r135a 10 a1359a 1 d13591a 0 r21=1.36605935

22 r51=1.49539243 d37211713=-179.88563964 r51a=1.49541577 d37211713a=-180.8101267 r95=1.40619884 d41252117=179.71024293 r95a=1.40607743 d41252117a=179.70556051 r135=1.40515655 d459513=-178.713858 r135a=1.40524679 d459513a=-178.72394678 r1713=1.39415756 r4933=1.37679203 r1713a=1.3940645 r4933a=1.37740545 r2117=1.39615186 r5337=1.37736574 r2117a=1.39625895 r5337a=1.37665051 r2521=1.39656343 r5733=1.08750885 r2521a=1.39645092 r5733a=1.08765743 r2913=1.08552068 r6137=1.08770608 r2913a=1.08552187 r6137a=1.08755768 r3317=1.08696934 r6549=1.08672006 r3317a=1.08681271 r6549a=1.08671607 r3721=1.08680829 r6953=1.08671641 r3721a=1.08702633 r6953a=1.08671028 r4125=1.08702855 a493317=120.82332788 r4125a=1.08696394 a493317a=120.7819255 r459=1.08640875 a533721=120.79335051 r459a=1.0864122 a533721a=120.80971722 a512=122.68667655 a573317=118.69790838 a512a=122.68353173 a573317a=118.75441793 a951=120.45956736 a613721=118.75537722 a951a=120.46589005 a613721a=118.70422372 a1359=118.14010295 a654933=120.06742294 a1359a=118.14295853 a654933a=120.09212566 a17135=120.91183973 a695337=120.10537376 a17135a=120.90860245 a695337a=120.08127697 a211713=120.27772219 d49331713=179.97026914 a211713a=120.27879365 d49331713a=180.21277191 a252117=119.48718338 d53372125=179.57427024 a252117a=119.48899787 d53372125a=179.93887074 a29135=119.20999992 d57331713=0.24681759 a29135a=119.20297698 d57331713a=0.29746488 a331713=119.59900187 d61372125=-0.39963685 a331713a=120.24871743 d61372125a=-0.04473598 a372117=120.26026298 d65493317=180.1691997 a372117a=119.67501156 d65493317a=179.88944484 a412521=120.11322558 d69533721=179.98111109 a412521a=119.60878185 d69533721a=179.99684793 a4595=119.23612307 a4595a=119.2437296 Ph4E, C2, ΔG298=0.0 kJ/mol d4213=168.04050681 0 1 d5123=89.99088197 C d9512=-227.10370937 C 1 r21 d9512a=-227.18847895 X 1 1. 2 90. d13591=-177.29501286 X 2 1. 1 90. 3 d4213 0 d13591a=-177.3068976 C 1 r51 2 a512 3 d5123 0 d171359=-0.989385 C 1 r51a 2 a512a 3 -d5123 0 d171359a=-0.97885814 C 2 r51 1 a512 4 d5123 0 d2117135=-0.07186991 C 2 r51a 1 a512a 4 -d5123 0 d2117135a=-0.07091661 C 5 r95 1 a951 2 d9512 0 d25211713=0.56333179 C 6 r95a 1 a951a 2 d9512a 0 d25211713a=0.55218453 C 7 r95 2 a951 1 d9512 0 d291359=178.9233112 C 8 r95a 2 a951a 1 d9512a 0 d291359a=178.93615885 C 5 r135 9 a1359 1 d13591 0 d3317135=-180.29582529 C 6 r135a 10 a1359a 1 d13591a 0 d3317135a=-179.89199105 C 7 r135 11 a1359 2 d13591 0

23 C 8 r135a 12 a1359a 2 d13591a 0 r51a=1.4953558 C 13 r1713 5 a17135 9 d171359 0 r95=1.40525153 C 14 r1713a 6 a17135a 10 d171359a 0 r95a=1.4061786 C 15 r1713 7 a17135 11 d171359 0 r135=1.4060879 C 16 r1713a 8 a17135a 12 d171359a 0 r135a=1.40518679 C 17 r2117 13 a211713 5 d2117135 0 r1713=1.39392548 C 18 r2117a 14 a211713a 6 d2117135a 0 r1713a=1.39413574 C 19 r2117 15 a211713 7 d2117135 0 r2117=1.39645966 C 20 r2117a 16 a211713a 8 d2117135a 0 r2117a=1.39617259 C 21 r2521 17 a252117 13 d25211713 0 r2521=1.39625703 C 22 r2521a 18 a252117a 14 d25211713a 0 r2521a=1.39654809 C 23 r2521 19 a252117 15 d25211713 0 r2913=1.0864121 C 24 r2521a 20 a252117a 16 d25211713a 0 r2913a=1.08551954 H 13 r2913 5 a29135 9 d291359 0 r3317=1.08703108 H 14 r2913a 6 a29135a 10 d291359a 0 r3317a=1.0869701 H 15 r2913 7 a29135 11 d291359 0 r3721=1.0868089 H 16 r2913a 8 a29135a 12 d291359a 0 r3721a=1.08680844 H 17 r3317 13 a331713 5 d3317135 0 r4125=1.08696595 H 18 r3317a 14 a331713a 6 d3317135a 0 r4125a=1.08702761 H 19 r3317 15 a331713 7 d3317135 0 r459=1.08552185 H 20 r3317a 16 a331713a 8 d3317135a 0 r459a=1.08641095 H 21 r3721 17 a372117 13 d37211713 0 a512=122.68008204 H 22 r3721a 18 a372117a 14 d37211713a 0 a512a=122.6902101 H 23 r3721 19 a372117 15 d37211713 0 a951=121.33100976 H 24 r3721a 20 a372117a 16 d37211713a 0 a951a=120.46293089 H 25 r4125 21 a412521 17 d41252117 0 a1359=118.14100423 H 26 r4125a 22 a412521a 18 d41252117a 0 a1359a=118.13926732 H 27 r4125 23 a412521 19 d41252117 0 a17135=120.96343505 H 28 r4125a 24 a412521a 20 d41252117a 0 a17135a=120.91186133 H 9 r459 5 a4595 13 d459513 0 a211713=120.20180205 H 10 r459a 6 a4595a 14 d459513a 0 a211713a=120.27868783 H 11 r459 7 a4595 15 d459513 0 a252117=119.48758099 H 12 r459a 8 a4595a 16 d459513a 0 a252117a=119.48634576 X 33 r4933 17 a493317 13 d49331713 0 a29135=119.24250874 X 34 r4933a 18 a493317a 14 d49331713a 0 a29135a=119.20924355 X 35 r4933 19 a493317 15 d49331713 0 a331713=119.67410288 X 36 r4933a 20 a493317a 16 d49331713a 0 a331713a=119.59798269 X 37 r5337 21 a533721 25 d53372125 0 a372117=120.25970889 X 38 r5337a 22 a533721a 26 d53372125a 0 a372117a=120.26061421 X 39 r5337 23 a533721 27 d53372125 0 a412521=120.11425593 X 40 r5337a 24 a533721a 28 d53372125a 0 a412521a=120.1155607 X 33 r5733 17 a573317 13 d57331713 0 a4595=119.20149875 X 34 r5733a 18 a573317a 14 d57331713a 0 a4595a=119.23795548 X 35 r5733 19 a573317 15 d57331713 0 d4213=11.9573075 X 36 r5733a 20 a573317a 16 d57331713a 0 d5123=89.99815987 X 37 r6137 21 a613721 25 d61372125 0 d9512=49.96619587 X 38 r6137a 22 a613721a 26 d61372125a 0 d9512a=-132.85538289 X 39 r6137 23 a613721 27 d61372125 0 d13591=-177.2869094 X 40 r6137a 24 a613721a 28 d61372125a 0 d13591a=-182.68403698 X 49 r6549 33 a654933 17 d65493317 0 d171359=-1.57186362 X 50 r6549a 34 a654933a 18 d65493317a 0 d171359a=0.96956271 X 51 r6549 35 a654933 19 d65493317 0 d2117135=1.12571767 X 52 r6549a 36 a654933a 20 d65493317a 0 d2117135a=0.07625402 X 53 r6953 37 a695337 21 d69533721 0 d25211713=-0.04124722 X 54 r6953a 38 a695337a 22 d69533721a 0 d25211713a=-0.55028101 X 55 r6953 39 a695337 23 d69533721 0 d291359=178.73282478 X 56 r6953a 40 a695337a 24 d69533721a 0 d291359a=181.05956567 d3317135=-179.19168957 r21=1.3660976 d3317135a=-179.69658227 r51=1.49539793 d37211713=-180.48204477

24 d37211713a=-180.10885416 C 13 r1713 5 a17135 9 d171359 0 d41252117=179.22378405 C 14 r1713 6 a17135 10 -d171359 0 d41252117a=180.27452805 C 15 r1713 7 a17135 11 d171359 0 d459513=-178.94269555 C 16 r1713 8 a17135 12 -d171359 0 d459513a=-181.26265262 C 17 r2117 13 a211713 5 d2117135 0 r4933=1.37690337 C 18 r2117 14 a211713 6 -d2117135 0 r4933a=1.37689256 C 19 r2117 15 a211713 7 d2117135 0 r5337=1.37764022 C 20 r2117 16 a211713 8 -d2117135 0 r5337a=1.37756651 C 21 r2521 17 a252117 13 d25211713 0 r5733=1.08760346 C 22 r2521 18 a252117 14 -d25211713 0 r5733a=1.0874698 C 23 r2521 19 a252117 15 d25211713 0 r6137=1.08766014 C 24 r2521 20 a252117 16 -d25211713 0 r6137a=1.08767068 H 13 r2913 5 a29135 9 d291359 0 r6549=1.08673742 H 14 r2913 6 a29135 10 -d291359 0 r6549a=1.086694 H 15 r2913 7 a29135 11 d291359 0 r6953=1.08671865 H 16 r2913 8 a29135 12 -d291359 0 r6953a=1.08671499 H 17 r3317 13 a331713 5 d3317135 0 a493317=120.81404185 H 18 r3317 14 a331713 6 -d3317135 0 a493317a=120.8104722 H 19 r3317 15 a331713 7 d3317135 0 a533721=120.78591755 H 20 r3317 16 a331713 8 -d3317135 0 a533721a=120.78139167 H 21 r3721 17 a372117 13 d37211713 0 a573317=118.7239291 H 22 r3721 18 a372117 14 -d37211713 0 a573317a=118.72435898 H 23 r3721 19 a372117 15 d37211713 0 a613721=118.76641599 H 24 r3721 20 a372117 16 -d37211713 0 a613721a=118.7749536 H 25 r4125 21 a412521 17 d41252117 0 a654933=120.07699892 H 26 r4125 22 a412521 18 -d41252117 0 a654933a=120.06799363 H 27 r4125 23 a412521 19 d41252117 0 a695337=120.09831624 H 28 r4125 24 a412521 20 -d41252117 0 a695337a=120.09582877 H 9 r459 5 a4595 13 d459513 0 d49331713=180.18573392 H 10 r459 6 a4595 14 -d459513 0 d49331713a=180.12029483 H 11 r459 7 a4595 15 d459513 0 d53372125=179.72384584 H 12 r459 8 a4595 16 -d459513 0 d53372125a=180.387925 d57331713=0.13964622 r21=1.35172938 d57331713a=-0.16719385 r51=1.50270697 d61372125=-0.34637575 r95=1.40292809 d61372125a=0.36062263 r135=1.40277888 d65493317=180.00744841 r1713=1.39495726 d65493317a=179.82254456 r2117=1.39536532 d69533721=179.91103537 r2521=1.39573387 d69533721a=180.00944546 r2913=1.086211 r3317=1.08697489

Ph4E, C2h, ΔG298=32.66 kJ/mol r3721=1.08674602 0 1 r4125=1.08703088 C r459=3.02598494 C 1 r21 a512=122.16703125 X 1 1. 2 90. a951=121.71060221 X 2 1. 1 90. 3 180. 0 a1359=118.30407943 C 1 r51 2 a512 3 d5123 0 a17135=120.92075349 C 1 r51 2 a512 3 -d5123 0 a211713=120.19347701 C 2 r51 1 a512 4 d5123 0 a252117=119.48034433 C 2 r51 1 a512 4 -d5123 0 a29135=119.16797947 C 5 r95 1 a951 2 d9512 0 a331713=119.66414124 C 6 r95 1 a951 2 -d9512 0 a372117=120.27751618 C 7 r95 2 a951 1 d9512 0 a412521=120.11390035 C 8 r95 2 a951 1 -d9512 0 a4595=86.19654937 C 5 r135 9 a1359 1 d13591 0 d5123=87.66311729 C 6 r135 10 a1359 1 -d13591 0 d9512=110.48888575 C 7 r135 11 a1359 2 d13591 0 d13591=-177.79755565 C 8 r135 12 a1359 2 -d13591 0 d171359=-0.23576486

25 d2117135=0.048603 X 35 r4933a 19 a493317a 15 d49331713a 0 d25211713=-0.04143811 X 36 r4933 20 a493317 16 -d49331713 0 d291359=179.81903272 X 37 r5337 21 a533721 25 d53372125 0 d3317135=-179.94547134 X 38 r5337a 22 a533721a 26 -d53372125a 0 d37211713=-179.96517337 X 39 r5337a 23 a533721a 27 d53372125a 0 d41252117=180.32936093 X 40 r5337 24 a533721 28 -d53372125 0 d459513=204.5256819 X 33 r5733 17 a573317 13 d57331713 0 X 34 r5733a 18 a573317a 14 -d57331713a 0

Ph4E, Ci, ΔG298=27.48 kJ/mol X 35 r5733a 19 a573317a 15 d57331713a 0 0 1 X 36 r5733 20 a573317 16 -d57331713 0 C X 37 r6137 21 a613721 25 d61372125 0 C 1 r21 X 38 r6137a 22 a613721a 26 -d61372125a 0 X 1 1. 2 90. X 39 r6137a 23 a613721a 27 d61372125a 0 X 2 1. 1 90. 3 180. 0 X 40 r6137 24 a613721 28 -d61372125 0 C 1 r51 2 a512 3 d5123 0 X 49 r6549 33 a654933 17 d65493317 0 C 1 r51a 2 a512a 3 -d5123 0 X 50 r6549a 34 a654933a 18 -d65493317a 0 C 2 r51a 1 a512a 4 d5123 0 X 51 r6549a 35 a654933a 19 d65493317a 0 C 2 r51 1 a512 4 -d5123 0 X 52 r6549 36 a654933 20 -d65493317 0 C 5 r95 1 a951 2 d9512 0 X 53 r6953 37 a695337 21 d69533721 0 C 6 r95a 1 a951a 2 -d9512a 0 X 54 r6953a 38 a695337a 22 -d69533721a 0 C 7 r95a 2 a951a 1 d9512a 0 X 55 r6953a 39 a695337a 23 d69533721a 0 C 8 r95 2 a951 1 -d9512 0 X 56 r6953 40 a695337 24 -d69533721 0 C 5 r135 9 a1359 1 d13591 0 C 6 r135a 10 a1359a 1 -d13591a 0 r21=1.35373768 C 7 r135a 11 a1359a 2 d13591a 0 r51=1.50424287 C 8 r135 12 a1359 2 -d13591 0 r51a=1.50144637 C 13 r1713 5 a17135 9 d171359 0 r95=1.40247936 C 14 r1713a 6 a17135a 10 -d171359a 0 r95a=1.40418934 C 15 r1713a 7 a17135a 11 d171359a 0 r135=1.40285384 C 16 r1713 8 a17135 12 -d171359 0 r135a=1.40356705 C 17 r2117 13 a211713 5 d2117135 0 r1713=1.39542577 C 18 r2117a 14 a211713a 6 -d2117135a 0 r1713a=1.39490395 C 19 r2117a 15 a211713a 7 d2117135a 0 r2117=1.39549746 C 20 r2117 16 a211713 8 -d2117135 0 r2117a=1.39504018 C 21 r2521 17 a252117 13 d25211713 0 r2521=1.39557069 C 22 r2521a 18 a252117a 14 -d25211713a 0 r2521a=1.39588357 C 23 r2521a 19 a252117a 15 d25211713a 0 r2913=1.08688944 C 24 r2521 20 a252117 16 -d25211713 0 r2913a=1.08507089 H 13 r2913 5 a29135 9 d291359 0 r3317=1.08703618 H 14 r2913a 6 a29135a 10 -d291359a 0 r3317a=1.08699751 H 15 r2913a 7 a29135a 11 d291359a 0 r3721=1.08671661 H 16 r2913 8 a29135 12 -d291359 0 r3721a=1.08676325 H 17 r3317 13 a331713 5 d3317135 0 r4125=1.08696924 H 18 r3317a 14 a331713a 6 -d3317135a 0 r4125a=1.08701858 H 19 r3317a 15 a331713a 7 d3317135a 0 r459=1.08654648 H 20 r3317 16 a331713 8 -d3317135 0 r459a=1.08570532 H 21 r3721 17 a372117 13 d37211713 0 a512=122.22412834 H 22 r3721a 18 a372117a 14 -d37211713a 0 a512a=122.7688367 H 23 r3721a 19 a372117a 15 d37211713a 0 a951=119.5348662 H 24 r3721 20 a372117 16 -d37211713 0 a951a=121.00132844 H 25 r4125 21 a412521 17 d41252117 0 a1359=118.32101095 H 26 r4125a 22 a412521a 18 -d41252117a 0 a1359a=118.05814113 H 27 r4125a 23 a412521a 19 d41252117a 0 a17135=120.86803739 H 28 r4125 24 a412521 20 -d41252117 0 a17135a=121.00848642 H 9 r459 5 a4595 13 d459513 0 a211713=120.21114806 H 10 r459a 6 a4595a 14 -d459513a 0 a211713a=120.26730584 H 11 r459a 7 a4595a 15 d459513a 0 a252117=119.49287556 H 12 r459 8 a4595 16 -d459513 0 a252117a=119.38895349 X 33 r4933 17 a493317 13 d49331713 0 a29135=119.6586327 X 34 r4933a 18 a493317a 14 -d49331713a 0 a29135a=119.33695602

26 a331713=119.66122998 d61372125a=0.32656368 a331713a=119.5805641 d65493317=179.9734078 a372117=120.2319671 d65493317a=179.84110741 a372117a=120.31836293 d69533721=179.96685624 a412521=120.1272944 d69533721a=180.02779548 a412521a=120.1408637 a4595=119.16872442 Ph4E, C2v, ΔG298=34.99 kJ/mol a4595a=119.71253073 0 1 d5123=92.17231974 C d9512=81.21073946 C 1 r21 d9512a=-122.0500304 X 1 1. 2 90. d13591=-177.57196821 X 2 1. 1 90. 3 0. 0 d13591a=-182.67113158 C 1 r51 2 a512 3 d5123 0 d171359=-0.21325299 C 1 r51 2 a512 3 -d5123 0 d171359a=0.8709335 C 2 r51 1 a512 4 -d5123 0 d2117135=0.10045489 C 2 r51 1 a512 4 d5123 0 d2117135a=-0.05947661 C 5 r95 1 a951 2 d9512 0 d25211713=-0.08061388 C 6 r95 1 a951 2 -d9512 0 d25211713a=-0.36985197 C 7 r95 2 a951 1 -d9512 0 d291359=180.78489524 C 8 r95 2 a951 1 d9512 0 d291359a=181.22281403 C 5 r135 9 a1359 1 d13591 0 d3317135=-179.60397696 C 6 r135 10 a1359 1 -d13591 0 d3317135a=-179.89115266 C 7 r135 11 a1359 2 -d13591 0 d37211713=-179.95165849 C 8 r135 12 a1359 2 d13591 0 d37211713a=-180.07916672 C 13 r1713 5 a17135 9 d171359 0 d41252117=180.17741648 C 14 r1713 6 a17135 10 -d171359 0 d41252117a=180.14729994 C 15 r1713 7 a17135 11 -d171359 0 d459513=180.19008213 C 16 r1713 8 a17135 12 d171359 0 d459513a=178.98851079 C 17 r2117 13 a211713 5 d2117135 0 r4933=1.37676716 C 18 r2117 14 a211713 6 -d2117135 0 r4933a=1.37687158 C 19 r2117 15 a211713 7 -d2117135 0 r5337=1.37681414 C 20 r2117 16 a211713 8 d2117135 0 r5337a=1.37717526 C 21 r2521 17 a252117 13 d25211713 0 r5733=1.08779609 C 22 r2521 18 a252117 14 -d25211713 0 r5733a=1.08751125 C 23 r2521 19 a252117 15 -d25211713 0 r6137=1.08760549 C 24 r2521 20 a252117 16 d25211713 0 r6137a=1.0876652 H 13 r2913 5 a29135 9 d291359 0 r6549=1.08673076 H 14 r2913 6 a29135 10 -d291359 0 r6549a=1.0867129 H 15 r2913 7 a29135 11 -d291359 0 r6953=1.08663907 H 16 r2913 8 a29135 12 d291359 0 r6953a=1.08670646 H 17 r3317 13 a331713 5 d3317135 0 a493317=120.84151748 H 18 r3317 14 a331713 6 -d3317135 0 a493317a=120.81952834 H 19 r3317 15 a331713 7 -d3317135 0 a533721=120.81866145 H 20 r3317 16 a331713 8 d3317135 0 a533721a=120.77056276 H 21 r3721 17 a372117 13 d37211713 0 a573317=118.7725378 H 22 r3721 18 a372117 14 -d37211713 0 a573317a=118.73745565 H 23 r3721 19 a372117 15 -d37211713 0 a613721=118.7219741 H 24 r3721 20 a372117 16 d37211713 0 a613721a=118.77912252 H 25 r4125 21 a412521 17 d41252117 0 a654933=120.05885604 H 26 r4125 22 a412521 18 -d41252117 0 a654933a=120.06333962 H 27 r4125 23 a412521 19 -d41252117 0 a695337=120.13240232 H 28 r4125 24 a412521 20 d41252117 0 a695337a=120.11890322 H 9 r459 5 a4595 13 d459513 0 d49331713=179.74428754 H 10 r459 6 a4595 14 -d459513 0 d49331713a=180.08502072 H 11 r459 7 a4595 15 -d459513 0 d53372125=180.08485178 H 12 r459 8 a4595 16 d459513 0 d53372125a=180.34457731 d57331713=-0.35644452 r21=1.34797919 d57331713a=-0.16049303 r51=1.50257556 d61372125=0.05646391 r95=1.40197599

27 r135=1.401976 C 23 r2521a 19 a252117a 15 d25211713a 0 r1713=1.39522758 C 24 r2521 20 a252117 16 -d25211713 0 r2117=1.39567277 H 13 r2913 5 a29135 9 d291359 0 r2521=1.3956728 H 14 r2913a 6 a29135a 10 -d291359a 0 r2913=1.08682827 H 15 r2913a 7 a29135a 11 d291359a 0 r3317=1.08701309 H 16 r2913 8 a29135 12 -d291359 0 r3721=1.08675396 H 17 r3317 13 a331713 5 d3317135 0 r4125=1.08701307 H 18 r3317a 14 a331713a 6 -d3317135a 0 r459=3.41907827 H 19 r3317a 15 a331713a 7 d3317135a 0 a512=122.43238755 H 20 r3317 16 a331713 8 -d3317135 0 a951=120.72642564 H 21 r3721 17 a372117 13 d37211713 0 a1359=118.50787425 H 22 r3721a 18 a372117a 14 -d37211713a 0 a17135=120.7863757 H 23 r3721a 19 a372117a 15 d37211713a 0 a211713=120.18610076 H 24 r3721 20 a372117 16 -d37211713 0 a252117=119.54588567 H 25 r4125 21 a412521 17 d41252117 0 a29135=119.41578037 H 26 r4125a 22 a412521a 18 -d41252117a 0 a331713=119.69690652 H 27 r4125a 23 a412521a 19 d41252117a 0 a372117=120.22704046 H 28 r4125 24 a412521 20 -d41252117 0 a412521=120.11693355 H 9 r459 5 a4595 13 d459513 0 a4595=78.89868424 H 10 r459a 6 a4595a 14 -d459513a 0 d5123=89.9999583 H 11 r459a 7 a4595a 15 d459513a 0 d9512=91.1572249 H 12 r459 8 a4595 16 -d459513 0 d13591=-177.73590546 X 33 r4933 17 a493317 13 d49331713 0 d171359=-0.40386299 X 34 r4933a 18 a493317a 14 -d49331713a 0 d2117135=0.24556903 X 35 r4933a 19 a493317a 15 d49331713a 0 d25211713=-0.07766967 X 36 r4933 20 a493317 16 -d49331713 0 d291359=179.91568438 X 37 r5337 21 a533721 25 d53372125 0 d3317135=-179.6651094 X 38 r5337a 22 a533721a 26 -d53372125a 0 d37211713=-180.00556756 X 39 r5337a 23 a533721a 27 d53372125a 0 d41252117=180.16737068 X 40 r5337 24 a533721 28 -d53372125 0 d459513=208.41899467 X 33 r5733 17 a573317 13 d57331713 0 X 34 r5733a 18 a573317a 14 -d57331713a 0

Ph4E, Cs, ΔG298=30.44 kJ/mol X 35 r5733a 19 a573317a 15 d57331713a 0 0 1 X 36 r5733 20 a573317 16 -d57331713 0 C X 37 r6137 21 a613721 25 d61372125 0 C 1 r21 X 38 r6137a 22 a613721a 26 -d61372125a 0 X 1 1. 2 90. X 39 r6137a 23 a613721a 27 d61372125a 0 X 2 1. 1 90. 3 0. 0 X 40 r6137 24 a613721 28 -d61372125 0 C 1 r51 2 a512 3 d5123 0 X 49 r6549 33 a654933 17 d65493317 0 C 1 r51a 2 a512a 3 -d5123 0 X 50 r6549a 34 a654933a 18 -d65493317a 0 C 2 r51a 1 a512a 4 d5123 0 X 51 r6549a 35 a654933a 19 d65493317a 0 C 2 r51 1 a512 4 -d5123 0 X 52 r6549 36 a654933 20 -d65493317 0 C 5 r95 1 a951 2 d9512 0 X 53 r6953 37 a695337 21 d69533721 0 C 6 r95a 1 a951a 2 -d9512a 0 X 54 r6953a 38 a695337a 22 -d69533721a 0 C 7 r95a 2 a951a 1 d9512a 0 X 55 r6953a 39 a695337a 23 d69533721a 0 C 8 r95 2 a951 1 -d9512 0 X 56 r6953 40 a695337 24 -d69533721 0 C 5 r135 9 a1359 1 d13591 0 C 6 r135a 10 a1359a 1 -d13591a 0 r21=1.34969849 C 7 r135a 11 a1359a 2 d13591a 0 r51=1.50261329 C 8 r135 12 a1359 2 -d13591 0 r51a=1.50265097 C 13 r1713 5 a17135 9 d171359 0 r95=1.40275119 C 14 r1713a 6 a17135a 10 -d171359a 0 r95a=1.40274109 C 15 r1713a 7 a17135a 11 d171359a 0 r135=1.40187539 C 16 r1713 8 a17135 12 -d171359 0 r135a=1.40187693 C 17 r2117 13 a211713 5 d2117135 0 r1713=1.39568581 C 18 r2117a 14 a211713a 6 -d2117135a 0 r1713a=1.39568337 C 19 r2117a 15 a211713a 7 d2117135a 0 r2117=1.39509384 C 20 r2117 16 a211713 8 -d2117135 0 r2117a=1.39509701 C 21 r2521 17 a252117 13 d25211713 0 r2521=1.39615706 C 22 r2521a 18 a252117a 14 -d25211713a 0 r2521a=1.39615117

28 r2913=1.08637464 r6137a=1.08763998 r2913a=1.08637569 r6549=1.08673906 r3317=1.08702008 r6549a=1.08673898 r3317a=1.08702039 r6953=1.08668559 r3721=1.08675723 r6953a=1.08668559 r3721a=1.08675723 a493317=120.84169037 r4125=1.08700055 a493317a=120.84167417 r4125a=1.08700096 a533721=120.8021719 r459=1.08684365 a533721a=120.80197053 r459a=1.08684352 a573317=118.76674162 a512=122.75716195 a573317a=118.76649589 a512a=122.75513616 a613721=118.74507776 a951=120.080405 a613721a=118.74523742 a951a=120.08109559 a654933=120.07351298 a1359=118.41875328 a654933a=120.07371681 a1359a=118.41896149 a695337=120.1260249 a17135=120.82644158 a695337a=120.12599623 a17135a=120.8264051 d49331713=179.87789071 a211713=120.19719425 d49331713a=180.12632333 a211713a=120.19697932 d53372125=179.65689378 a252117=119.52476471 d53372125a=180.34100982 a252117a=119.52496023 d57331713=-0.06083031 a29135=119.42929492 d57331713a=0.06404735 a29135a=119.4290817 d61372125=-0.31547296 a331713=119.6653162 d61372125a=0.31188846 a331713a=119.66573142 d65493317=180.04177516 a372117=120.24640621 d65493317a=179.95778474 a372117a=120.24635495 d69533721=179.99286549 a412521=120.11649591 d69533721a=180.00514272 a412521a=120.11634253 a4595=119.37090749 a4595a=119.37003871 d5123=90.00471853 d9512=101.76788224 d9512a=-101.76080336 d13591=-177.32959032 d13591a=-182.66739674 d171359=-0.60246489 d171359a=0.59738575 d2117135=0.03816596 d2117135a=-0.03450985 d25211713=0.23799172 d25211713a=-0.23889247 d291359=179.36155543 d291359a=180.62983804 d3317135=-179.83519288 d3317135a=-180.16436295 d37211713=-179.85342474 d37211713a=-180.14768542 d41252117=179.98646881 d41252117a=180.0116729 d459513=180.65339501 d459513a=179.34941884 r4933=1.37692657 r4933a=1.37692762 r5337=1.37708474 r5337a=1.37708491 r5733=1.08768227 r5733a=1.08768199 r6137=1.0876399

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