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Cytosine: para-sulphonato-calix[4]arene assemblies: in solution, in the solid-state and on the surface of hybrid silver nanoparticles

Yannick Tauran 1,2, Moez Rhimi 3, Ryohei Ueno 4, Marie Grosso 1, Arnaud Brioude 1, Erwann Janneau 5, Kinga Suwinska 6,7,*, Rima Kassab 8, Patrick Shahgaldian9, Alessandro Cumbo 9, Bernard Fenet 10, Beomjoon Kim 2,4 and Anthony W. Coleman 1,*

1 LMI, CNRS UMR 5615 Univ. Lyon 1, Villeurbanne, F69622, France ; E-mail: yannick.tauran@ univ-lyon 1.fr 2 LIMMS/CNRS-IIS (UMI 2820), University of Tokyo, Tokyo, Japan; E-mail: [email protected] 3 BMSSI UMR5086-CNRS/Univ. Lyon 1, Institut de Biologie et Chimie des Proteines FR3302, 7 Passage du Vercors, Lyon, F69367, France ; E-mail: [email protected] 4 CIRMM, Institute of Industrial Science, University of Tokyo, Tokyo, Japan; E-mail: [email protected] 5 Centre de diffractométrie Henri Longchambon, Univ. Lyon 1, Villeurbanne, F69622, France ; E-mail: [email protected] 6 Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, PL-01 224 Warszawa, Poland; E-mail: [email protected] 7 Faculty of Biology and Environmental Sciences, Cardinal Stefan, Wyszynski University in Warsaw, Wo´ycickiego 1/3, PL-01 938, Warszawa, Poland; 8 University of Balamand, Faculty of Sciences- Department of Chemistry P.O Box : 100 – Tripoli-Lebanon; E-mail : [email protected] 9 Fachhochschule Nordwestschweiz, Hochschule für Lifesciences, Gründenstrasse 40, 4132 Muttenz, Switzerland; E-mail : [email protected] 10 Centre Commun RMN, Univ. Lyon 1, Villeurbanne, F69622 France ; E-mail : [email protected]

* Dr Antony W. Coleman; E-Mail: [email protected] 1.fr; Tel.: +33 4-42-43-10-27; Fax: +33 4-72-44 -06-18.

* Dr Kinga Suwinska; E-Mail: [email protected]; Tel.: +48-22343-3399 Supporting Information

Figure S1 A graph of the 1/ΔIf vs. 1/[H]0 for cytosine / para-sulphonato-calix[4]arene complex with n= 0,5

Figure S2 A graph of the 1/ΔIf vs. 1/[H]0 for cytosine / para –sulphonato-calix[4]arene

complex with n= 2 Figure S3 A graph of the 1/ΔIf vs. 1/[H]0 for cytosine / para-sulphonato-calix[4]arene silver nanoparticles with n= 1

Figure S4 A graph of the 1/ΔIf vs. 1/[H]0 for cytosine / para-sulphonato-calix[4]arene silver nanoparticles with n= 2 Figure S5 TEM picture of para-sulphonato-calix[4]arene capped silver nanoparticles. The

black bar represent 100 nm.

TEM Imaging protocole:

The TEM sample was prepared by dropping 6 μL of 1.10-4M solution of para-sulphonato- calix[4]arene capped silver nanoparticles on carbon coated grid (50 mesh, Ted Pella). After 30 seconds, the sample was wicked from the grid by touching its edge with a piece of filter paper. TEM studies were conducted by using a Topcon EM 002B microscope, operating with an accelerating voltage of 200 kV. Diffusion NMR experiments

Table S1 List of calculated Ka from diffusion coefficients of the complex cytosine / para- sulphonato-calix[4]arene cytosine concentration (mM) 0,92 0,84 0,78 0,77 0,74 para-sulphonato-calix[4]arene concentration (mM) 0,09 0,41 0,92 4,46 8,32 cytosine diffusion coefficient (10-6 cm2s-1) 7,545 6,368 5,521 4,087 3,688 para-sulphonato-calix[4]arene diffusion coefficient (10-6 cm2s-1) 3,175 3,2855 3,3375 3,2555 3,1805 Mole fraction of the complex 0,0422 0,3059 0,4956 0,8169 0,9063 Ka (M-1) 862,09 2880,41 1842,82 1165,06 1265,24

Crystal data

2(C28H20O16S4)·8(C4H6N3O)·CH4O·18(H2O) Z = 1

Mr = 2734.71 F(000) = 1430.000

-3 Triclinic, P¯1 Dx = 1.595 Mg m Hall symbol: -P 1 Mo K radiation,  = 0.7107 Å a = 12.423 (1) Å Cell parameters from 7049 reflections b = 14.894 (2) Å  = 3.4–29.4° c = 17.357 (1) Å  = 0.27 mm-1  = 71.444 (9)° T = 100 K  = 71.745 (8)° Block, colorless  = 75.420 (9)° 0.33 × 0.19 × 0.15 mm V = 2849.8 (5) Å3

Data collection

Xcalibur, Atlas, Gemini ultra 12946 independent reflections diffractometer Radiation source: Enhance (Mo) X-ray Source 9331 reflections with I > 2.0(I) graphite Rint = 0.058

-1 Detector resolution: 10.4685 pixels mm max = 29.5°, min = 3.4°  scans h = -1515 Absorption correction: analytical k = -1719 CrysAlis PRO, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)

Tmin = 0.943, Tmax = 0.970 l = 023 25103 measured reflections

Refinement

Refinement on F2 Hydrogen site location: difference Fourier map Least-squares matrix: full H-atom parameters constrained R[F2 > 2(F2)] = 0.067 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/ [A0*T0(x) + A1*T1(x) ···+ An-1]*Tn-1(x)] where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1- 2 2 (deltaF/6*sigmaF) ] Ai are: 674. 0.107E + 04 607. 216. 37.8

2 wR(F ) = 0.196 (/)max = 0.002

-3 S = 0.90 max = 1.87 e Å

-3 12946 reflections min = -1.15 e Å 884 parameters Extinction correction: Larson (1970), Equation 22 45 restraints Extinction coefficient: 43 (9) Primary atom site location: structure-invariant direct methods

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq Occ. (<1) S1 0.58225 (8) 0.29029 (6) 0.69870 (6) 0.0151 O2 0.6558 (3) 0.3322 (2) 0.72241 (18) 0.0233 O3 0.4605 (2) 0.3103 (2) 0.74307 (17) 0.0214 O4 0.6210 (2) 0.18665 (19) 0.70693 (17) 0.0198 C5 0.5921 (3) 0.3434 (2) 0.5907 (2) 0.0141 C6 0.6501 (3) 0.4203 (2) 0.5459 (2) 0.0131 C7 0.6548 (3) 0.4604 (2) 0.4607 (2) 0.0123 C8 0.6005 (3) 0.4219 (3) 0.4218 (2) 0.0132 O9 0.6080 (2) 0.46400 (19) 0.33924 (16) 0.0171 H91 0.5675 0.4492 0.3178 0.0263* C10 0.5423 (3) 0.3442 (3) 0.4671 (2) 0.0148 C11 0.5395 (3) 0.3057 (2) 0.5515 (2) 0.0139 H111 0.5015 0.2539 0.5825 0.0170* C12 0.4877 (3) 0.2991 (3) 0.4255 (2) 0.0159 C13 0.5801 (3) 0.2425 (3) 0.3692 (2) 0.0157 C14 0.6395 (3) 0.1551 (3) 0.4046 (2) 0.0180 C15 0.7264 (3) 0.1028 (3) 0.3538 (3) 0.0198 S16 0.79747 (9) -0.00998 (7) 0.40228 (7) 0.0224 O17 0.7102 (3) -0.0624 (2) 0.4610 (2) 0.0289 O18 0.8661 (4) -0.0554 (2) 0.3362 (3) 0.0652 O19 0.8650 (4) 0.0117 (3) 0.4473 (4) 0.0673 C20 0.7542 (3) 0.1399 (3) 0.2673 (3) 0.0189 C21 0.6977 (3) 0.2285 (3) 0.2294 (2) 0.0168 C22 0.6092 (3) 0.2797 (3) 0.2815 (2) 0.0163 O23 0.5457 (2) 0.3661 (2) 0.25244 (17) 0.0195 H231 0.5654 0.3850 0.2013 0.0286* C24 0.7374 (3) 0.2684 (3) 0.1345 (2) 0.0187 C25 0.8521 (3) 0.3014 (3) 0.1110 (2) 0.0162 C26 0.8586 (3) 0.3884 (3) 0.1227 (2) 0.0164 O27 0.7561 (2) 0.4420 (2) 0.15120 (18) 0.0200 H271 0.7500 0.4900 0.1656 0.0302* C28 0.9649 (3) 0.4168 (3) 0.1062 (2) 0.0146 C29 1.0656 (3) 0.3548 (3) 0.0791 (2) 0.0150 C30 1.0593 (3) 0.2684 (3) 0.0681 (2) 0.0169 C31 0.9527 (3) 0.2414 (3) 0.0841 (2) 0.0156 H311 0.9493 0.1817 0.0775 0.0189* S32 1.18356 (8) 0.18304 (6) 0.04277 (6) 0.0154 O33 1.2838 (2) 0.2286 (2) 0.02315 (18) 0.0209 O34 1.1743 (2) 0.1590 (2) -0.02969 (17) 0.0208 O35 1.1787 (3) 0.1016 (2) 0.11668 (18) 0.0223 H291 1.1371 0.3719 0.0684 0.0180* C36 0.9727 (3) 0.5091 (3) 0.1222 (2) 0.0158 C37 0.9564 (3) 0.4984 (2) 0.2150 (2) 0.0134 C38 0.8494 (3) 0.5307 (2) 0.2660 (2) 0.0126 O39 0.7655 (2) 0.57936 (18) 0.22451 (16) 0.0153 H391 0.7005 0.5869 0.2551 0.0232* C40 0.8320 (3) 0.5156 (2) 0.3525 (2) 0.0146 C41 0.7168 (3) 0.5445 (2) 0.4108 (2) 0.0139 H411 0.7314 0.5711 0.4504 0.0174* H412 0.6690 0.5932 0.3781 0.0169* C42 0.9264 (3) 0.4727 (2) 0.3869 (2) 0.0133 C43 1.0330 (3) 0.4433 (2) 0.3370 (2) 0.0128 C44 1.0482 (3) 0.4540 (2) 0.2519 (2) 0.0136 H441 1.1204 0.4330 0.2193 0.0159* S45 1.15040 (7) 0.39463 (6) 0.38387 (5) 0.0130 O46 1.1575 (2) 0.4646 (2) 0.42237 (18) 0.0202 O47 1.2519 (2) 0.37717 (19) 0.31556 (17) 0.0172 O48 1.1240 (2) 0.30370 (19) 0.44469 (17) 0.0181 H421 0.9177 0.4634 0.4444 0.0158* H361 1.0494 0.5249 0.0919 0.0188* H362 0.9159 0.5609 0.1010 0.0185* H242 0.6811 0.3224 0.1151 0.0223* H241 0.7460 0.2184 0.1075 0.0218* H201 0.8115 0.1045 0.2339 0.0228* H141 0.6223 0.1300 0.4627 0.0216* H122 0.4400 0.2546 0.4686 0.0188* H121 0.4401 0.3479 0.3924 0.0191* H61 0.6854 0.4448 0.5727 0.0149* O49 0.3225 (2) 0.1653 (2) 0.81735 (17) 0.0185 H491 0.2987 0.1617 0.8677 0.0280* H492 0.3625 0.2075 0.7957 0.0280* O50 0.6712 (2) 0.4623 (2) 0.79953 (18) 0.0213 H501 0.6931 0.5091 0.7626 0.0322* H502 0.6623 0.4283 0.7751 0.0323* O51 0.2843 (2) 0.2282 (2) 0.61944 (18) 0.0202 C52 0.1833 (3) 0.2514 (2) 0.6529 (2) 0.0155 N53 0.1451 (3) 0.2425 (2) 0.7393 (2) 0.0146 C54 0.0358 (3) 0.2725 (2) 0.7805 (2) 0.0156 N55 0.0103 (3) 0.2618 (2) 0.8620 (2) 0.0184 H551 -0.0579 0.2819 0.8884 0.0221* H552 0.0635 0.2408 0.8887 0.0221* C56 -0.0471 (3) 0.3129 (3) 0.7324 (2) 0.0167 C57 -0.0128 (3) 0.3184 (3) 0.6499 (2) 0.0185 N58 0.0984 (3) 0.2873 (2) 0.6109 (2) 0.0163 H581 0.1179 0.2960 0.5571 0.0202* H571 -0.0664 0.3437 0.6183 0.0222* H561 -0.1230 0.3343 0.7577 0.0196* H531 0.1950 0.2202 0.7672 0.0171* O59 0.4299 (3) 0.8806 (2) 0.88440 (19) 0.0269 C60 0.4600 (3) 0.9083 (3) 0.8080 (3) 0.0195 N61 0.4173 (3) 0.9968 (2) 0.7636 (2) 0.0207 C62 0.4481 (4) 1.0267 (3) 0.6785 (3) 0.0223 C63 0.5259 (3) 0.9700 (3) 0.6319 (3) 0.0211 C64 0.5770 (3) 0.8789 (3) 0.6747 (2) 0.0169 N65 0.5412 (3) 0.8514 (2) 0.7595 (2) 0.0194 H651 0.5805 0.8010 0.7856 0.0231* N66 0.6578 (3) 0.8214 (2) 0.6351 (2) 0.0193 H662 0.6864 0.7657 0.6624 0.0230* H661 0.6844 0.8408 0.5824 0.0231* H631 0.5460 0.9902 0.5738 0.0261* H621 0.4142 1.0872 0.6519 0.0270* H611 0.3741 1.0373 0.7913 0.0245* O67 1.0774 (3) -0.0031 (2) 0.89558 (19) 0.0239 C68 0.9827 (3) 0.0370 (3) 0.8841 (3) 0.0194 N69 0.9660 (3) 0.0670 (2) 0.8044 (2) 0.0186 C70 0.8630 (4) 0.1083 (3) 0.7865 (3) 0.0198 N71 0.8568 (3) 0.1290 (3) 0.7092 (2) 0.0233 H711 0.7914 0.1523 0.6969 0.0280* H712 0.9153 0.1117 0.6707 0.0283* C72 0.7673 (4) 0.1284 (3) 0.8533 (3) 0.0227 C73 0.7828 (4) 0.0998 (3) 0.9314 (3) 0.0240 N74 0.8880 (3) 0.0564 (2) 0.9458 (2) 0.0210 H741 0.8929 0.0331 0.9967 0.0249* H731 0.7205 0.1088 0.9773 0.0285* H721 0.6962 0.1599 0.8432 0.0270* H691 1.0250 0.0587 0.7631 0.0221* O75 0.2186 (3) 0.6453 (2) 0.07916 (18) 0.0234 H751 0.2420 0.6120 0.1202 0.0349* H752 0.2714 0.6734 0.0475 0.0350* O76 0.4187 (3) 0.3554 (2) 0.9008 (2) 0.0276 H761 0.3671 0.3219 0.9306 0.0412* H762 0.4360 0.3460 0.8551 0.0410* O77 0.6777 (3) 0.7147 (2) 0.8474 (2) 0.0321 H771 0.6733 0.6577 0.8695 0.0482* H772 0.6831 0.7352 0.8844 0.0480* O78 0.2930 (3) 0.4631 (2) 0.0374 (2) 0.0346 H781 0.3441 0.4747 -0.0060 0.0512* H782 0.2683 0.5139 0.0509 0.0514* O79 0.5670 (3) 0.3060 (3) 0.0037 (2) 0.0424 H791 0.5683 0.2520 0.0358 0.0472* H792 0.5234 0.3205 -0.0270 0.0472* O80 0.5242 (3) 0.4501 (3) 0.0974 (2) 0.0374 H801 0.4760 0.4879 0.1203 0.0551* H802 0.4923 0.4346 0.0699 0.0545* O81 0.1208 (6) 0.7929 (5) 0.4655 (4) 0.0336 0.6638 O82 0.0868 (13) 0.8237 (10) 0.4572 (9) 0.0295 0.3362 C83 0.0701 (4) 0.8058 (3) 0.5345 (3) 0.0244 N84 -0.0234 (6) 0.8735 (5) 0.5486 (4) 0.0185 0.6638 N85 -0.0294 (13) 0.8555 (11) 0.5817 (8) 0.0195 0.3362 C86 -0.0840 (6) 0.8905 (5) 0.6242 (4) 0.0219 0.6638 H851 -0.0865 0.8800 0.5592 0.0212* 0.3362 C87 -0.0501 (15) 0.8461 (12) 0.6647 (11) 0.0200 0.3362 N88 -0.1366 (10) 0.8982 (8) 0.7038 (7) 0.0263 0.3362 C89 -0.0442 (8) 0.8306 (7) 0.6955 (6) 0.0277 0.6638 H891 -0.0814 0.8387 0.7492 0.0359* 0.6638 C90 0.0493 (9) 0.7622 (6) 0.6843 (5) 0.0248 0.6638 C91 0.0282 (19) 0.7782 (15) 0.7074 (12) 0.0252 0.3362 C92 0.1209 (13) 0.7273 (9) 0.6642 (8) 0.0238 0.3362 H901 0.0753 0.7218 0.7305 0.0298* 0.6638 N93 0.1061 (7) 0.7496 (7) 0.6056 (6) 0.0275 0.6638 N94 0.1398 (15) 0.7423 (15) 0.5810 (13) 0.0270 0.3362 H931 0.1550 0.6976 0.6027 0.0302* 0.6638 H941 0.2012 0.7104 0.5550 0.0242* 0.3362 H921 0.1711 0.6808 0.6924 0.0280* 0.3362 H911 0.0192 0.7697 0.7645 0.0322* 0.3362 N95 -0.1717 (5) 0.9609 (4) 0.6273 (4) 0.0277 0.6638 H882 -0.1968 0.9203 0.6848 0.0320* 0.3362 H951 -0.2106 0.9722 0.6748 0.0600* 0.6638 H952 -0.1904 0.9958 0.5819 0.0600* 0.6638 H881 -0.1402 0.9016 0.7532 0.0320* 0.3362 H841 -0.0487 0.9080 0.5055 0.0258* 0.6638 O96 0.6710 (4) 0.9839 (3) 0.7782 (3) 0.0512 H961 0.7138 0.9639 0.8106 0.0764* H962 0.6386 1.0377 0.7837 0.0764* O97 0.4986 (7) 0.8884 (6) 0.0535 (5) 0.0450 0.5000 C98 0.500000 (10) 1.000000 (10) 0.000000 (10) 0.0634 H985 0.5550 1.0249 0.0129 0.0960* 0.5000 H984 0.5214 1.0037 -0.0591 0.0960* 0.5000 H986 0.5756 0.9631 -0.0151 0.0960* 0.5000 H971 0.5555 0.8546 0.0314 0.0680* 0.5000

Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23 S1 0.0178 (4) 0.0134 (4) 0.0123 (4) -0.0007 (3) -0.0043 (3) -0.0018 (3) O2 0.0342 (16) 0.0242 (15) 0.0164 (14) -0.0080 (12) -0.0109 (12) -0.0051 (11) O3 0.0230 (14) 0.0213 (14) 0.0131 (13) -0.0003 (11) -0.0001 (10) -0.0026 (10) O4 0.0265 (14) 0.0125 (13) 0.0174 (14) 0.0007 (10) -0.0080 (11) -0.0007 (10) C5 0.0107 (15) 0.0122 (16) 0.0154 (17) 0.0035 (12) -0.0006 (12) -0.0050 (13) C6 0.0128 (15) 0.0133 (16) 0.0121 (16) 0.0020 (12) -0.0035 (12) -0.0049 (13) C7 0.0122 (15) 0.0097 (15) 0.0125 (16) 0.0022 (12) -0.0008 (12) -0.0049 (12) C8 0.0117 (15) 0.0139 (16) 0.0130 (17) 0.0029 (12) -0.0028 (12) -0.0066 (13) O9 0.0209 (13) 0.0195 (13) 0.0100 (12) -0.0055 (10) -0.0035 (10) -0.0016 (10) C10 0.0113 (15) 0.0122 (16) 0.0188 (18) 0.0016 (12) -0.0011 (13) -0.0067 (13) C11 0.0125 (15) 0.0108 (16) 0.0148 (17) 0.0020 (12) -0.0007 (12) -0.0044 (13) C12 0.0139 (16) 0.0173 (17) 0.0158 (18) -0.0019 (13) -0.0009 (13) -0.0067 (14) C13 0.0134 (16) 0.0176 (17) 0.0191 (18) -0.0033 (13) -0.0018 (13) -0.0105 (14) C14 0.0222 (18) 0.0164 (17) 0.0147 (18) -0.0062 (14) -0.0011 (14) -0.0043 (14) C15 0.0210 (18) 0.0130 (17) 0.024 (2) -0.0029 (14) -0.0051 (15) -0.0038 (14) S16 0.0227 (5) 0.0127 (4) 0.0277 (5) -0.0020 (3) -0.0021 (4) -0.0046 (4) O17 0.0306 (16) 0.0222 (15) 0.0217 (16) -0.0008 (12) -0.0002 (12) 0.0013 (12) O18 0.088 (3) 0.0153 (16) 0.036 (2) 0.0194 (18) 0.031 (2) 0.0018 (15) O19 0.067 (3) 0.0227 (18) 0.138 (5) -0.0036 (18) -0.077 (3) -0.008 (2) C20 0.0178 (17) 0.0159 (17) 0.023 (2) -0.0008 (14) -0.0004 (14) -0.0113 (15) C21 0.0150 (16) 0.0196 (18) 0.0175 (18) -0.0029 (13) -0.0024 (13) -0.0088 (14) C22 0.0130 (16) 0.0192 (18) 0.0192 (19) -0.0015 (13) -0.0043 (13) -0.0092 (14) O23 0.0192 (13) 0.0220 (14) 0.0149 (13) 0.0018 (11) -0.0050 (10) -0.0051 (10) C24 0.0197 (18) 0.0206 (18) 0.0166 (19) -0.0014 (14) -0.0024 (14) -0.0097 (14) C25 0.0201 (18) 0.0186 (18) 0.0101 (16) -0.0022 (14) -0.0037 (13) -0.0050 (13) C26 0.0152 (17) 0.0185 (18) 0.0124 (17) 0.0028 (13) -0.0026 (13) -0.0048 (13) O27 0.0162 (13) 0.0214 (14) 0.0232 (15) 0.0030 (10) -0.0033 (10) -0.0136 (11) C28 0.0180 (17) 0.0152 (17) 0.0080 (16) -0.0001 (13) -0.0006 (12) -0.0040 (13) C29 0.0155 (16) 0.0178 (17) 0.0097 (16) -0.0031 (13) -0.0006 (12) -0.0034 (13) C30 0.0218 (18) 0.0153 (17) 0.0108 (17) 0.0003 (14) -0.0020 (13) -0.0042 (13) C31 0.0172 (17) 0.0163 (17) 0.0118 (17) -0.0017 (13) 0.0006 (13) -0.0068 (13) S32 0.0162 (4) 0.0149 (4) 0.0118 (4) 0.0014 (3) -0.0014 (3) -0.0043 (3) O33 0.0151 (13) 0.0199 (14) 0.0237 (15) -0.0034 (10) 0.0024 (10) -0.0075 (11) O34 0.0224 (14) 0.0227 (14) 0.0159 (14) 0.0034 (11) -0.0039 (11) -0.0098 (11) O35 0.0262 (15) 0.0186 (14) 0.0171 (14) 0.0003 (11) -0.0069 (11) 0.0003 (11) C36 0.0159 (17) 0.0167 (17) 0.0114 (17) 0.0009 (13) -0.0042 (13) -0.0013 (13) C37 0.0162 (16) 0.0078 (15) 0.0129 (17) -0.0027 (12) -0.0008 (12) -0.0007 (12) C38 0.0132 (16) 0.0091 (15) 0.0133 (17) -0.0003 (12) -0.0035 (12) -0.0010 (12) O39 0.0121 (12) 0.0163 (12) 0.0139 (12) 0.0030 (9) -0.0029 (9) -0.0036 (10) C40 0.0150 (16) 0.0103 (16) 0.0150 (17) -0.0013 (12) -0.0004 (13) -0.0028 (13) C41 0.0133 (16) 0.0122 (16) 0.0134 (17) 0.0015 (12) -0.0010 (12) -0.0045 (13) C42 0.0188 (17) 0.0080 (15) 0.0118 (16) -0.0040 (12) -0.0005 (13) -0.0027 (12) C43 0.0118 (15) 0.0118 (16) 0.0142 (17) -0.0011 (12) -0.0048 (12) -0.0019 (12) C44 0.0129 (16) 0.0122 (16) 0.0144 (17) 0.0003 (12) -0.0015 (12) -0.0054 (13) S45 0.0127 (4) 0.0127 (4) 0.0122 (4) 0.0009 (3) -0.0032 (3) -0.0037 (3) O46 0.0216 (14) 0.0188 (13) 0.0254 (15) 0.0006 (11) -0.0121 (11) -0.0098 (11) O47 0.0137 (12) 0.0169 (13) 0.0175 (13) 0.0017 (10) -0.0022 (10) -0.0046 (10) O48 0.0206 (13) 0.0174 (13) 0.0139 (13) -0.0029 (10) -0.0041 (10) -0.0014 (10) O49 0.0211 (13) 0.0209 (14) 0.0130 (13) -0.0020 (10) -0.0014 (10) -0.0079 (10) O50 0.0248 (14) 0.0195 (14) 0.0180 (14) -0.0024 (11) -0.0040 (11) -0.0052 (11) O51 0.0179 (13) 0.0183 (13) 0.0196 (14) 0.0007 (10) 0.0005 (10) -0.0065 (11) C52 0.0215 (18) 0.0069 (15) 0.0152 (17) -0.0005 (13) -0.0028 (13) -0.0021 (12) N53 0.0162 (15) 0.0118 (14) 0.0143 (15) 0.0012 (11) -0.0046 (11) -0.0034 (11) C54 0.0176 (17) 0.0083 (15) 0.0181 (18) -0.0004 (12) -0.0024 (13) -0.0031 (13) N55 0.0164 (15) 0.0197 (16) 0.0160 (16) 0.0021 (12) -0.0031 (12) -0.0056 (12) C56 0.0158 (17) 0.0135 (17) 0.0178 (18) 0.0019 (13) -0.0038 (13) -0.0039 (13) C57 0.0197 (18) 0.0144 (17) 0.0205 (19) 0.0002 (13) -0.0076 (14) -0.0033 (14) N58 0.0199 (15) 0.0137 (14) 0.0121 (15) 0.0004 (11) -0.0024 (11) -0.0030 (11) O59 0.0330 (17) 0.0257 (15) 0.0180 (15) -0.0014 (12) -0.0012 (12) -0.0081 (12) C60 0.0202 (18) 0.0183 (18) 0.022 (2) -0.0011 (14) -0.0053 (14) -0.0094 (15) N61 0.0202 (16) 0.0188 (16) 0.0225 (17) 0.0025 (12) -0.0032 (13) -0.0112 (13) C62 0.0235 (19) 0.0144 (18) 0.026 (2) 0.0006 (14) -0.0081 (16) -0.0029 (15) C63 0.0232 (19) 0.0176 (18) 0.0183 (19) 0.0025 (14) -0.0055 (15) -0.0032 (14) C64 0.0165 (17) 0.0152 (17) 0.0197 (19) -0.0011 (13) -0.0062 (14) -0.0051 (14) N65 0.0236 (17) 0.0159 (15) 0.0171 (16) 0.0026 (12) -0.0058 (13) -0.0059 (12) N66 0.0184 (15) 0.0171 (15) 0.0189 (16) 0.0016 (12) -0.0030 (12) -0.0055 (12) O67 0.0240 (15) 0.0236 (15) 0.0228 (15) 0.0034 (11) -0.0087 (11) -0.0072 (12) C68 0.0242 (19) 0.0133 (17) 0.0188 (19) -0.0007 (14) -0.0051 (15) -0.0039 (14) N69 0.0196 (16) 0.0175 (16) 0.0176 (16) -0.0031 (12) -0.0028 (12) -0.0050 (12) C70 0.0246 (19) 0.0142 (17) 0.021 (2) -0.0027 (14) -0.0078 (15) -0.0040 (14) N71 0.0256 (18) 0.0275 (18) 0.0170 (17) -0.0011 (14) -0.0071 (13) -0.0071 (14) C72 0.0212 (19) 0.0190 (19) 0.023 (2) -0.0002 (15) -0.0064 (15) -0.0012 (15) C73 0.026 (2) 0.0199 (19) 0.022 (2) -0.0011 (15) -0.0045 (16) -0.0037 (15) N74 0.0240 (17) 0.0195 (16) 0.0162 (16) 0.0007 (13) -0.0053 (13) -0.0037 (13) O75 0.0242 (14) 0.0267 (15) 0.0156 (14) -0.0010 (12) -0.0038 (11) -0.0043 (11) O76 0.0324 (17) 0.0308 (16) 0.0204 (15) -0.0093 (13) -0.0028 (12) -0.0087 (12) O77 0.048 (2) 0.0232 (16) 0.0225 (16) 0.0073 (14) -0.0158 (14) -0.0058 (12) O78 0.0383 (19) 0.0319 (18) 0.0299 (18) -0.0056 (14) -0.0032 (14) -0.0087 (14) O79 0.040 (2) 0.049 (2) 0.037 (2) -0.0170 (17) -0.0202 (16) 0.0095 (17) O80 0.0357 (19) 0.046 (2) 0.0260 (18) 0.0061 (15) -0.0065 (14) -0.0151 (15) O81 0.038 (4) 0.028 (4) 0.021 (3) 0.004 (3) -0.006 (3) 0.001 (3) O82 0.035 (6) 0.029 (6) 0.015 (4) 0.007 (4) -0.010 (4) 0.000 (4) C83 0.030 (2) 0.0184 (19) 0.023 (2) -0.0072 (16) -0.0069 (17) -0.0001 (15) N84 0.022 (2) 0.013 (3) 0.018 (4) -0.008 (2) -0.006 (3) 0.004 (3) N85 0.025 (4) 0.009 (5) 0.015 (6) 0.000 (3) -0.006 (5) 0.007 (5) C86 0.031 (3) 0.018 (3) 0.022 (3) -0.011 (2) -0.009 (2) -0.005 (2) C87 0.030 (5) 0.017 (5) 0.018 (5) -0.006 (4) -0.010 (4) -0.007 (4) N88 0.029 (4) 0.019 (4) 0.031 (4) -0.003 (3) -0.007 (3) -0.009 (3) C89 0.037 (4) 0.028 (4) 0.021 (4) -0.012 (3) -0.008 (3) -0.005 (3) C90 0.038 (5) 0.016 (4) 0.023 (4) -0.009 (3) -0.016 (4) 0.002 (3) C91 0.036 (5) 0.026 (5) 0.018 (5) -0.010 (4) -0.005 (5) -0.010 (4) C92 0.036 (5) 0.016 (5) 0.019 (5) -0.005 (4) -0.015 (4) 0.003 (4) N93 0.028 (5) 0.017 (2) 0.037 (6) 0.002 (3) -0.016 (4) -0.004 (3) N94 0.027 (5) 0.017 (3) 0.037 (6) 0.002 (4) -0.016 (4) -0.004 (3) N95 0.030 (3) 0.025 (3) 0.029 (3) -0.008 (2) -0.004 (2) -0.009 (2) O96 0.053 (3) 0.046 (2) 0.059 (3) -0.0042 (19) -0.024 (2) -0.013 (2) O97 0.036 (4) 0.048 (5) 0.042 (5) 0.001 (3) 0.000 (3) -0.015 (4) C98 0.053 (5) 0.092 (8) 0.066 (7) -0.022 (5) -0.003 (5) -0.053 (6)

Geometric parameters (Å, º)

S1—O2 1.443 (3) N55—H552 0.863 S1—O3 1.469 (3) C56—C57 1.341 (6) S1—O4 1.471 (3) C56—H561 0.929 S1—C5 1.765 (4) C57—N58 1.369 (5) C5—C6 1.391 (5) C57—H571 0.926 C5—C11 1.382 (5) N58—H581 0.861 C6—C7 1.397 (5) O59—C60 1.220 (5) C6—H61 0.927 C60—N61 1.368 (5) C7—C8 1.402 (5) C60—N65 1.391 (5) C7—C41 1.512 (5) N61—C62 1.356 (5) C8—O9 1.353 (4) N61—H611 0.862 C8—C10 1.402 (5) C62—C63 1.354 (6) O9—H91 0.814 C62—H621 0.931 C10—C11 1.386 (5) C63—C64 1.420 (5) C10—C12 1.509 (5) C63—H631 0.926 C11—H111 0.932 C64—N65 1.352 (5) C12—C13 1.523 (5) C64—N66 1.313 (5) C12—H122 0.976 N65—H651 0.863 C12—H121 0.969 N66—H662 0.864 C13—C14 1.382 (5) N66—H661 0.848 C13—C22 1.405 (5) O67—C68 1.224 (5) C14—C15 1.402 (5) C68—N69 1.377 (5) C14—H141 0.930 C68—N74 1.360 (5) C15—S16 1.769 (4) N69—C70 1.358 (5) C15—C20 1.386 (6) N69—H691 0.865 S16—O17 1.432 (3) C70—N71 1.301 (5) S16—O18 1.446 (4) C70—C72 1.424 (6) S16—O19 1.458 (4) N71—H711 0.863 C20—C21 1.392 (5) N71—H712 0.867 C20—H201 0.932 C72—C73 1.346 (6) C21—C22 1.414 (5) C72—H721 0.931 C21—C24 1.524 (5) C73—N74 1.365 (5) C22—O23 1.363 (5) C73—H731 0.939 O23—H231 0.817 N74—H741 0.857 C24—C25 1.516 (5) O75—H751 0.819 C24—H242 0.970 O75—H752 0.821 C24—H241 0.969 O76—H761 0.847 C25—C26 1.400 (5) O76—H762 0.803 C25—C31 1.384 (5) O77—H771 0.820 C26—O27 1.360 (4) O77—H772 0.819 C26—C28 1.403 (5) O78—H781 0.821 O27—H271 0.809 O78—H782 0.820 C28—C29 1.403 (5) O79—H791 0.820 C28—C36 1.517 (5) O79—H792 0.819 C29—C30 1.382 (5) O80—H801 0.810 C29—H291 0.932 O80—H802 0.820 C30—C31 1.400 (5) O81—C83 1.217 (8) C30—S32 1.771 (4) O82—C83 1.241 (14) C31—H311 0.946 C83—N84 1.348 (9) S32—O33 1.463 (3) C83—N93 1.386 (11) S32—O34 1.456 (3) C83—N85 1.427 (17) S32—O35 1.456 (3) C83—N94 1.35 (2) C36—C37 1.520 (5) N84—C86 1.360 (10) C36—H361 0.981 N84—H841 0.862 C36—H362 0.968 N85—H851 0.860 C37—C38 1.412 (5) N85—C87 1.35 (2) C37—C44 1.399 (5) C86—C89 1.424 (10) C38—O39 1.374 (4) C86—N95 1.309 (9) C38—C40 1.399 (5) C87—N88 1.29 (2) O39—H391 0.819 C87—C91 1.41 (3) C40—C41 1.522 (5) N88—H882 0.859 C40—C42 1.398 (5) N88—H881 0.862 C41—H411 0.976 C89—H891 0.934 C41—H412 0.966 C89—C90 1.346 (14) C42—C43 1.388 (5) C90—H901 0.931 C42—H421 0.938 C90—N93 1.376 (12) C43—C44 1.391 (5) C91—C92 1.36 (2) C43—S45 1.775 (4) C91—H911 0.931 C44—H441 0.935 C92—N94 1.34 (2) S45—O46 1.438 (3) C92—H921 0.931 S45—O47 1.469 (3) N93—H931 0.860 S45—O48 1.467 (3) N94—H941 0.867 O49—H491 0.818 N95—H951 0.860 O49—H492 0.821 N95—H952 0.860 O50—H501 0.820 O96—H961 0.830 O50—H502 0.802 O96—H962 0.821 O51—C52 1.219 (5) O97—C98 1.627 (8) C52—N53 1.397 (5) O97—H971 0.821 C52—N58 1.371 (5) C98—H986i 0.965 N53—C54 1.359 (5) C98—H985i 0.964 N53—H531 0.842 C98—H984i 0.963 C54—N55 1.315 (5) C98—H985 0.964 C54—C56 1.423 (5) C98—H984 0.963 N55—H551 0.857 C98—H986 0.965

O2—S1—O3 113.08 (18) N55—C54—C56 123.0 (3) O2—S1—O4 112.58 (17) C54—N55—H551 120.3 O3—S1—O4 110.90 (17) C54—N55—H552 120.5 O2—S1—C5 107.23 (17) H551—N55—H552 118.7 O3—S1—C5 106.86 (16) C54—C56—C57 118.3 (3) O4—S1—C5 105.67 (16) C54—C56—H561 120.7 S1—C5—C6 122.0 (3) C57—C56—H561 121.0 S1—C5—C11 117.5 (3) C56—C57—N58 122.4 (4) C6—C5—C11 120.6 (3) C56—C57—H571 118.9 C5—C6—C7 119.9 (3) N58—C57—H571 118.7 C5—C6—H61 119.9 C52—N58—C57 122.2 (3) C7—C6—H61 120.3 C52—N58—H581 118.2 C6—C7—C8 118.9 (3) C57—N58—H581 119.3 C6—C7—C41 120.8 (3) O59—C60—N61 123.0 (4) C8—C7—C41 120.3 (3) O59—C60—N65 121.9 (4) C7—C8—O9 116.1 (3) N61—C60—N65 115.1 (4) C7—C8—C10 121.1 (3) C60—N61—C62 123.1 (3) O9—C8—C10 122.8 (3) C60—N61—H611 118.0 C8—O9—H91 117.3 C62—N61—H611 118.6 C8—C10—C11 118.6 (3) N61—C62—C63 121.3 (4) C8—C10—C12 121.9 (3) N61—C62—H621 119.0 C11—C10—C12 119.5 (3) C63—C62—H621 119.8 C10—C11—C5 120.9 (3) C62—C63—C64 118.1 (4) C10—C11—H111 119.6 C62—C63—H631 121.1 C5—C11—H111 119.4 C64—C63—H631 120.7 C10—C12—C13 110.2 (3) C63—C64—N65 118.3 (3) C10—C12—H122 109.4 C63—C64—N66 122.4 (4) C13—C12—H122 108.1 N65—C64—N66 119.3 (3) C10—C12—H121 110.6 C60—N65—C64 124.0 (3) C13—C12—H121 109.4 C60—N65—H651 117.2 H122—C12—H121 109.1 C64—N65—H651 117.6 C12—C13—C14 119.8 (3) C64—N66—H662 120.8 C12—C13—C22 120.8 (3) C64—N66—H661 119.2 C14—C13—C22 119.3 (3) H662—N66—H661 120.0 C13—C14—C15 120.6 (4) O67—C68—N69 120.4 (4) C13—C14—H141 120.3 O67—C68—N74 124.5 (4) C15—C14—H141 119.1 N69—C68—N74 115.0 (3) C14—C15—S16 118.7 (3) C68—N69—C70 124.3 (4) C14—C15—C20 119.7 (4) C68—N69—H691 117.8 S16—C15—C20 121.6 (3) C70—N69—H691 117.9 C15—S16—O17 107.01 (19) N69—C70—N71 118.7 (4) C15—S16—O18 107.1 (2) N69—C70—C72 118.2 (4) O17—S16—O18 113.3 (2) N71—C70—C72 123.2 (4) C15—S16—O19 105.2 (2) C70—N71—H711 120.1 O17—S16—O19 109.7 (3) C70—N71—H712 120.7 O18—S16—O19 113.8 (3) H711—N71—H712 118.5 C15—C20—C21 121.4 (4) C70—C72—C73 117.8 (4) C15—C20—H201 119.1 C70—C72—H721 120.9 C21—C20—H201 119.5 C73—C72—H721 121.3 C20—C21—C22 118.2 (4) C72—C73—N74 121.2 (4) C20—C21—C24 118.8 (3) C72—C73—H731 120.0 C22—C21—C24 122.9 (3) N74—C73—H731 118.8 C21—C22—C13 120.8 (3) C73—N74—C68 123.4 (4) C21—C22—O23 124.2 (3) C73—N74—H741 118.5 C13—C22—O23 115.0 (3) C68—N74—H741 117.6 C22—O23—H231 111.7 H751—O75—H752 105.6 C21—C24—C25 110.4 (3) H761—O76—H762 105.8 C21—C24—H242 110.1 H771—O77—H772 105.0 C25—C24—H242 109.1 H781—O78—H782 105.7 C21—C24—H241 109.0 H791—O79—H792 115.7 C25—C24—H241 108.9 H801—O80—H802 105.5 H242—C24—H241 109.3 O81—C83—N84 124.0 (5) C24—C25—C26 120.9 (3) O81—C83—N93 121.0 (5) C24—C25—C31 119.8 (3) N84—C83—N93 114.9 (5) C26—C25—C31 119.1 (3) O82—C83—N85 119.6 (8) C25—C26—O27 115.5 (3) O82—C83—N94 125.9 (10) C25—C26—C28 121.3 (3) N85—C83—N94 114.5 (9) O27—C26—C28 123.2 (3) C83—N84—C86 126.5 (6) C26—O27—H271 123.7 C83—N84—H841 116.5 C26—C28—C29 118.4 (3) C86—N84—H841 116.9 C26—C28—C36 121.5 (3) C83—N85—H851 116.9 C29—C28—C36 119.9 (3) C83—N85—C87 123.7 (13) C28—C29—C30 120.3 (3) H851—N85—C87 117.3 C28—C29—H291 119.8 N84—C86—C89 116.5 (7) C30—C29—H291 119.9 N84—C86—N95 119.2 (6) C29—C30—C31 120.7 (3) C89—C86—N95 124.3 (7) C29—C30—S32 122.0 (3) N85—C87—N88 121.8 (16) C31—C30—S32 117.0 (3) N85—C87—C91 117.3 (16) C30—C31—C25 120.1 (3) N88—C87—C91 121.0 (15) C30—C31—H311 120.1 C87—N88—H882 119.2 C25—C31—H311 119.8 C87—N88—H881 120.8 C30—S32—O33 107.54 (18) H882—N88—H881 118.9 C30—S32—O34 105.65 (17) C86—C89—H891 120.9 O33—S32—O34 112.08 (17) C86—C89—C90 119.0 (8) C30—S32—O35 106.05 (17) H891—C89—C90 120.1 O33—S32—O35 112.37 (18) C89—C90—H901 119.8 O34—S32—O35 112.60 (18) C89—C90—N93 121.1 (9) C28—C36—C37 111.8 (3) H901—C90—N93 119.2 C28—C36—H361 108.2 C87—C91—C92 119.8 (16) C37—C36—H361 108.2 C87—C91—H911 121.0 C28—C36—H362 109.9 C92—C91—H911 119.1 C37—C36—H362 109.9 C91—C92—N94 120.4 (15) H361—C36—H362 108.7 C91—C92—H921 120.1 C36—C37—C38 121.6 (3) N94—C92—H921 119.4 C36—C37—C44 119.8 (3) C83—N93—C90 122.0 (7) C38—C37—C44 118.6 (3) C83—N93—H931 119.1 C37—C38—O39 115.4 (3) C90—N93—H931 117.4 C37—C38—C40 121.7 (3) C83—N94—C92 124.2 (14) O39—C38—C40 122.9 (3) C83—N94—H941 117.6 C38—O39—H391 114.6 C92—N94—H941 118.1 C38—C40—C41 123.6 (3) C86—N95—H951 120.0 C38—C40—C42 118.0 (3) C86—N95—H952 120.0 C41—C40—C42 118.4 (3) H951—N95—H952 120.0 C40—C41—C7 112.7 (3) H961—O96—H962 105.6 C40—C41—H411 107.8 C98—O97—H971 109.1 C7—C41—H411 108.0 O97—C98—O97i 179.993 C40—C41—H412 109.2 O97—C98—H986i 109.2 C7—C41—H412 109.8 O97i—C98—H986i 70.8 H411—C41—H412 109.2 O97—C98—H985i 70.7 C40—C42—C43 120.8 (3) O97i—C98—H985i 109.3 C40—C42—H421 119.8 H986i—C98—H985i 70.3 C43—C42—H421 119.3 O97—C98—H984i 70.6 C42—C43—C44 120.9 (3) O97i—C98—H984i 109.4 C42—C43—S45 118.4 (3) H986i—C98—H984i 70.2 C44—C43—S45 120.8 (3) H985i—C98—H984i 109.6 C37—C44—C43 119.8 (3) O97—C98—H985 109.3 C37—C44—H441 120.4 O97i—C98—H985 70.7 C43—C44—H441 119.8 H986i—C98—H985 109.7 C43—S45—O46 106.57 (16) H985i—C98—H985 180.0 C43—S45—O47 106.12 (16) H984i—C98—H985 70.4 O46—S45—O47 113.54 (17) O97—C98—H984 109.4 C43—S45—O48 106.24 (16) O97i—C98—H984 70.6 O46—S45—O48 113.13 (17) H986i—C98—H984 109.8 O47—S45—O48 110.63 (16) H985i—C98—H984 70.4 H491—O49—H492 108.2 H984i—C98—H984 180.0 H501—O50—H502 105.0 O97—C98—H986 70.8 O51—C52—N53 121.3 (3) O97i—C98—H986 109.2 O51—C52—N58 124.1 (3) H986i—C98—H986 180.0 N53—C52—N58 114.5 (3) H985i—C98—H986 109.7 C52—N53—C54 125.0 (3) H984i—C98—H986 109.8 C52—N53—H531 117.0 H985—C98—H984 109.6 C54—N53—H531 117.8 H985—C98—H986 70.3 N53—C54—N55 119.6 (3) H984—C98—H986 70.2 N53—C54—C56 117.5 (3)

Symmetry code: (i) -x+1, -y+2, -z.

Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A O9—H91···O23 0.81 2.04 2.774 (7) 150 O23— 0.82 1.92 2.649 (7) 149 H231···O80 O27— 0.81 1.99 2.773 (7) 162 H271···O39 C29— 0.93 2.47 3.373 (7) 164 (1) H291···O78ii O39— 0.82 2.19 2.860 (7) 139 (1) H391···O3iii O39—H391···O9 0.82 2.26 2.797 (7) 123 C24— 0.97 2.38 3.332 (7) 168 H242···O80 O49— 0.82 1.96 2.704 (7) 152 (1) H491···O34iv O49—H492···O3 0.82 2.00 2.824 (7) 180 (1) O50— 0.82 1.93 2.744 (7) 174 (1) H501···O47v O50—H502···O2 0.80 1.96 2.754 (7) 172 N55— 0.86 2.02 2.853 (7) 165 (1) H551···O75vi N55— 0.86 2.16 3.004 (7) 166 (1) H552···O34iv N58— 0.86 1.90 2.738 (7) 165 (1) H581···O48vii N53— 0.84 1.92 2.760 (7) 172 H531···O49 N65— 0.86 1.85 2.694 (7) 166 H651···O77 N66— 0.86 2.03 2.839 (7) 156 (1) H662···O47v N66— 0.85 2.12 2.924 (7) 158 (1) H661···O17viii C63— 0.93 2.51 3.221 (7) 134 (1) H631···O17viii C62— 0.93 2.33 3.236 (7) 163 (1) H621···O51viii N61— 0.86 2.00 2.805 (7) 155 (1) H611···O49viii N71—H711···O4 0.86 2.01 2.846 (7) 162 N74— 0.86 1.91 2.752 (7) 167 (1) H741···O67ix C73— 0.94 2.56 3.493 (7) 172 (1) H731···O59x N69— 0.87 1.83 2.689 (7) 170 (1) H691···O18xi O75— 0.82 1.92 2.726 (7) 168 (1) H751···O50iii O75— 0.82 1.98 2.757 (7) 157 (1) H752···O79xii O76— 0.85 1.96 2.774 (7) 161 (1) H761···O33iv O76—H762···O3 0.80 2.09 2.884 (7) 171 O77— 0.82 2.05 2.782 (7) 148 (1) H771···O78iii O77— 0.82 2.03 2.841 (7) 172 (1) H772···O33v O78— 0.82 2.15 2.920 (7) 157 (1) H781···O80xii O78— 0.82 2.07 2.883 (7) 175 H782···O75 O79— 0.82 2.02 2.838 (7) 179 (1) H791···O59iii O79— 0.82 1.95 2.769 (7) 179 (1) H792···O76xiii O80— 0.81 2.05 2.822 (7) 159 (1) H801···O50iii O80— 0.82 2.38 2.939 (7) 126 H802···O79 N85— 0.86 2.39 3.082 (7) 138 (1) H851···O19xiv C86— 1.20 2.39 3.195 (7) 123 (1) H851···O19xiv C86— 1.20 2.47 3.288 (7) 123 (1) H851···O82 C89— 0.93 2.59 3.504 (7) 168 (1) H891···O35iii C92— 1.20 2.46 3.272 (7) 123 (1) H931···O81 N95— 0.86 1.96 2.798 (7) 165 (1) H951···O96vii N95— 0.86 2.17 2.884 (7) 140 (1) H952···O19xiv N88— 0.86 2.14 2.995 (7) 169 (1) H881···O35iii N84— 0.86 1.85 2.653 (7) 155 (1) H841···O19xiv O96— 0.83 1.99 2.810 (7) 172 (1) H961···O35v O96— 0.82 2.19 2.862 (7) 139 (1) H962···O4viii O97— 0.82 2.18 2.994 (7) 174 (1) H971···O33xv

Symmetry codes: (ii) x+1, y, z; (iii) -x+1, -y+1, -z+1; (iv) x-1, y, z+1; (v) -x+2, -y+1, -z+1; (vi) -x, -y+1, -z+1; (vii) x-1, y, z; (viii) x, y+1, z; (ix) -x+2, -y, -z+2; (x) -x+1, -y+1, -z+2; (xi) -x+2, -y, -z+1; (xii) -x+1, -y+1, -z; (xiii) x, y, z-1; (xiv) x-1, y+1, z; (xv) -x+2, -y+1, -z. CIF File

data_global _audit_creation_date "12-03-30" _audit_creation_method CRYSTALS_ver_14.40

_oxford_structure_analysis_title 's1d7 in P -1' _chemical_name_systematic ? _chemical_melting_point ?

#looking for refcif

# Check this file using the IUCr facility at: # http://checkcif.iucr.org/

# The content below is held in the file 'script/refcif.dat'. This is a text # file which you may edit to reflect local conditions. # Items which need looking at are represented by a '?'. # Items for which there are choices are prefixed with 'choose from'.

_publ_contact_letter ; Please consider this CIF submission for publication as a Short Format Paper in Acta Crystallographica E. ; _publ_contact_author_name 'Anthony Other' _publ_contact_author_address ; Chemical Crystallography Laboratory, Department of Chemistry, University of Nowhere, Nowhere, NO1 4T, UK. ;

_publ_contact_author_phone '+44 1865 000000' _publ_contact_author_fax '+44 1865 000000' _publ_contact_author_email '[email protected]' _publ_requested_journal 'Section E' _publ_requested_category EO # choose from: FI FM FO CI CM CO AD _publ_requested_coeditor_name 'Prof William Clegg'

_publ_section_title # Title of paper - generally just the systematic or trivial name ; ? ;

# The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address _publ_author_footnote 'Other, Anthony N.' # Author 1 ; ? # Address for author 1 ; ; ? # Footnote for author 1 ; 'Else, S. O.' # Author 2 ; ? # Address 2 ; ; ? # Footnote 2 ;

_publ_section_abstract # Text of the abstract # (a) The Abstract must be self-contained and comprehensible # without the rest of the paper. This means no references # to atom names or to compound numbers; compounds must be # identified as the title compound, or by name or by some other # means such as derivatives of each other (e.g. "the # corresponding ketone"). # (b) The chemical formula of "the title compound" must be given. # (c) Any crystallographic molecular symmetry should be # mentioned, and also the presence of more than one molecule # in the asymmetric unit (i.e. anything other than Z'=1). ; ? ;

_publ_section_related_literature # Not in version 2.3.1 ############################################################### # Essential references (e.g. to the origin of the material studied, related # structural studies, and to information supporting the reported structure) # should be cited in this section, with appropriate very brief explanatory # text, for example `The synthesis of the complex is described by Jones # (2001). The anhydrous complex has essentially the same coordination # geometry (Smith, 2003).' In addition, all references included in the # supplementary materials, but not elsewhere in the published article, # should be given here. The simple text `For related literature, see:...' # may be used, but further details should be provided in the Comment # section, which forms part of the supplementary material. ############################################################### ; ? ;

_publ_section_comment # Text of the paper # Note that atoms are referenced as N2, not N(2) or N~2~ # If text containing () occur within (), the outer ones should be [] # Figures should be referenced as Fig. ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures - Start each caption on a new line after a blank line ; Fig. 1. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius.

;

_publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; In the absence of significant anomalous scattering, Friedel pairs were merged.

The absolute configuration was arbitrarily assigned.

The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal.

Changes in illuminated volume were kept to a minimum, and were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997).

G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098.

The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints (Cooper et al, 2010).

Cooper, R. I., Thompson, A. L. & Watkin, D. J. (2010). J. Appl. Cryst. 43, 1100-1107.

;

_publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ;

# Hand-made tables can be put in the cif. The number of columns # is set in the loop header. # The contants of each column can either be a piece of text # without any spaces (eg a number) or other text enclosed in " " # Remove the leading # in the following example

#geom_extra_table_head_A #; #Table 2. #Molecular parameters deviating most from MOGUL averages #; # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 #_geom_extra_tableA_col_4 # #Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d" #N5-C6-C4 129 124 "7 (\%)" #C3-O10-C2 105 109 "2 (\%)" #C6-O7 1.25 1.22 ".02 (\%A)" #

data_1

_exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K.

Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. ; _refine_special_details ; ? ; #------# _oxford_ data items, April 2010: # There is some uncertainty about the correct way of forming local data # names, e.g.

# _atom_site_special_shape_oxford # or # _oxford_atom_site_special_shape

# see: # http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace

# A reserved prefix, e.g. foo, must be used in the following way # " If the data file contains items defined in a DDL1 dictionary, the # local data names assigned under the reserved prefix must contain it as # their first component, e.g. _foo_atom_site_my_item. "

# However, this seems to say the opposite: # http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html

# According to advice from the IUCr, CRYSTALS is correct #------# End of 'script/refcif.dat' #end of refcif _cell_length_a 12.4230(10) _cell_length_b 14.894(2) _cell_length_c 17.3570(10) _cell_angle_alpha 71.444(9) _cell_angle_beta 71.745(8) _cell_angle_gamma 75.420(9) _cell_volume 2849.8(5)

_symmetry_cell_setting 'triclinic' _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' '-x,-y,-z'

loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z 1

# Given Formula = C60 H60 N3 O12 S6 # Dc = 1.41 Fooo = 1432.00 Mu = 3.07 M = 1207.55 # Found Formula = C44.50 H65 N12 O29.50 S4 # Dc = 1.59 FOOO = 1432.00 Mu = 2.72 M = 1368.33

_chemical_formula_sum 'C89 H128 N24 O59 S8' _chemical_formula_moiety ; 2(C28 H20 O16 S4), 8(C4 H6 N3 O), C H4 O, 18(H2 O) ; _chemical_compound_source ? _chemical_formula_weight 2734.71

_cell_measurement_reflns_used 7049 _cell_measurement_theta_min 3.4045 _cell_measurement_theta_max 29.4302 _cell_measurement_temperature 100

_exptl_crystal_description 'block' _exptl_crystal_colour 'colorless' _exptl_crystal_size_min 0.146 _exptl_crystal_size_mid 0.193 _exptl_crystal_size_max 0.332

_exptl_crystal_density_diffrn 1.595 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1430.000 _exptl_absorpt_coefficient_mu 0.272

# Sheldrick geometric approximatio 0.95 0.96 _exptl_absorpt_correction_T_min 0.943 _exptl_absorpt_correction_T_max 0.970 _exptl_absorpt_correction_type 'analytical' _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator 'graphite' _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_detector_area_resol_mean 10.4685 _diffrn_measurement_method \w

# If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Gemini, (Oxford Diffraction, 2006)' _computing_cell_refinement 'CrysAlis, (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis, (Oxford Diffraction, 2002)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ?

_diffrn_ambient_temperature 100 _diffrn_reflns_number 25103 _reflns_number_total 12946 _diffrn_reflns_av_R_equivalents 0.058 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 12946 # Theoretical number of reflections is about 31748

_diffrn_reflns_theta_min 3.411 _diffrn_reflns_theta_max 29.494 _diffrn_measured_fraction_theta_max 0.815

_diffrn_reflns_theta_full 26.198 _diffrn_measured_fraction_theta_full 0.982

_diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 23 _reflns_limit_h_min -15 _reflns_limit_h_max 15 _reflns_limit_k_min -17 _reflns_limit_k_max 19 _reflns_limit_l_min 0 _reflns_limit_l_max 23

_oxford_diffrn_Wilson_B_factor 1.74 _oxford_diffrn_Wilson_scale 0.44

_atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap

_refine_diff_density_min -1.15 _refine_diff_density_max 1.87

# The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold

# The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 12946 _refine_ls_number_restraints 45 _refine_ls_number_parameters 884 _oxford_refine_ls_R_factor_ref 0.0949 _refine_ls_wR_factor_ref 0.1957 _refine_ls_goodness_of_fit_ref 0.9014 _refine_ls_shift/su_max 0.0014569 _refine_ls_shift/su_mean 0.0000224

# The values computed with all filters except I/sigma _oxford_reflns_number_all 12946 _refine_ls_R_factor_all 0.0949 _refine_ls_wR_factor_all 0.1957

# The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 9331 _refine_ls_R_factor_gt 0.0671 _refine_ls_wR_factor_gt 0.1519

# choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration '.'

_refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr #undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 674. 0.107E+04 607. 216. 37.8 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C., Guagliardi, A., Grazia, A., Moliterni, G., Polidori, G. & Spagna, R. (1999). J. App. Cryst. 32, 115-119.

Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294.

Oxford Diffraction, (2010). CrysAlisPro.

Oxford Diffraction, (2006). Gemini User Manual.

Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982.

Watkin D.J. (1994). Acta Cryst, A50, 411-437.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint

loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens S1 S 0.58225(8) 0.29029(6) 0.69870(6) 0.0151 1.0000 Uani ...... O2 O 0.6558(3) 0.3322(2) 0.72241(18) 0.0233 1.0000 Uani ...... O3 O 0.4605(2) 0.3103(2) 0.74307(17) 0.0214 1.0000 Uani ...... O4 O 0.6210(2) 0.18665(19) 0.70693(17) 0.0198 1.0000 Uani ...... C5 C 0.5921(3) 0.3434(2) 0.5907(2) 0.0141 1.0000 Uani ...... C6 C 0.6501(3) 0.4203(2) 0.5459(2) 0.0131 1.0000 Uani ...... C7 C 0.6548(3) 0.4604(2) 0.4607(2) 0.0123 1.0000 Uani ...... C8 C 0.6005(3) 0.4219(3) 0.4218(2) 0.0132 1.0000 Uani ...... O9 O 0.6080(2) 0.46400(19) 0.33924(16) 0.0171 1.0000 Uani ...... H91 H 0.5675 0.4492 0.3178 0.0263 1.0000 Uiso R . . . . . C10 C 0.5423(3) 0.3442(3) 0.4671(2) 0.0148 1.0000 Uani ...... C11 C 0.5395(3) 0.3057(2) 0.5515(2) 0.0139 1.0000 Uani ...... H111 H 0.5015 0.2539 0.5825 0.0170 1.0000 Uiso R . . . . . C12 C 0.4877(3) 0.2991(3) 0.4255(2) 0.0159 1.0000 Uani ...... C13 C 0.5801(3) 0.2425(3) 0.3692(2) 0.0157 1.0000 Uani ...... C14 C 0.6395(3) 0.1551(3) 0.4046(2) 0.0180 1.0000 Uani ...... C15 C 0.7264(3) 0.1028(3) 0.3538(3) 0.0198 1.0000 Uani ...... S16 S 0.79747(9) -0.00998(7) 0.40228(7) 0.0224 1.0000 Uani ...... O17 O 0.7102(3) -0.0624(2) 0.4610(2) 0.0289 1.0000 Uani ...... O18 O 0.8661(4) -0.0554(2) 0.3362(3) 0.0652 1.0000 Uani ...... O19 O 0.8650(4) 0.0117(3) 0.4473(4) 0.0673 1.0000 Uani ...... C20 C 0.7542(3) 0.1399(3) 0.2673(3) 0.0189 1.0000 Uani ...... C21 C 0.6977(3) 0.2285(3) 0.2294(2) 0.0168 1.0000 Uani ...... C22 C 0.6092(3) 0.2797(3) 0.2815(2) 0.0163 1.0000 Uani ...... O23 O 0.5457(2) 0.3661(2) 0.25244(17) 0.0195 1.0000 Uani ...... H231 H 0.5654 0.3850 0.2013 0.0286 1.0000 Uiso R . . . . . C24 C 0.7374(3) 0.2684(3) 0.1345(2) 0.0187 1.0000 Uani ...... C25 C 0.8521(3) 0.3014(3) 0.1110(2) 0.0162 1.0000 Uani ...... C26 C 0.8586(3) 0.3884(3) 0.1227(2) 0.0164 1.0000 Uani ...... O27 O 0.7561(2) 0.4420(2) 0.15120(18) 0.0200 1.0000 Uani ...... H271 H 0.7500 0.4900 0.1656 0.0302 1.0000 Uiso R . . . . . C28 C 0.9649(3) 0.4168(3) 0.1062(2) 0.0146 1.0000 Uani ...... C29 C 1.0656(3) 0.3548(3) 0.0791(2) 0.0150 1.0000 Uani ...... C30 C 1.0593(3) 0.2684(3) 0.0681(2) 0.0169 1.0000 Uani ...... C31 C 0.9527(3) 0.2414(3) 0.0841(2) 0.0156 1.0000 Uani ...... H311 H 0.9493 0.1817 0.0775 0.0189 1.0000 Uiso R . . . . . S32 S 1.18356(8) 0.18304(6) 0.04277(6) 0.0154 1.0000 Uani ...... O33 O 1.2838(2) 0.2286(2) 0.02315(18) 0.0209 1.0000 Uani ...... O34 O 1.1743(2) 0.1590(2) -0.02969(17) 0.0208 1.0000 Uani ...... O35 O 1.1787(3) 0.1016(2) 0.11668(18) 0.0223 1.0000 Uani ...... H291 H 1.1371 0.3719 0.0684 0.0180 1.0000 Uiso R . . . . . C36 C 0.9727(3) 0.5091(3) 0.1222(2) 0.0158 1.0000 Uani ...... C37 C 0.9564(3) 0.4984(2) 0.2150(2) 0.0134 1.0000 Uani ...... C38 C 0.8494(3) 0.5307(2) 0.2660(2) 0.0126 1.0000 Uani ...... O39 O 0.7655(2) 0.57936(18) 0.22451(16) 0.0153 1.0000 Uani ...... H391 H 0.7005 0.5869 0.2551 0.0232 1.0000 Uiso R . . . . . C40 C 0.8320(3) 0.5156(2) 0.3525(2) 0.0146 1.0000 Uani ...... C41 C 0.7168(3) 0.5445(2) 0.4108(2) 0.0139 1.0000 Uani ...... H411 H 0.7314 0.5711 0.4504 0.0174 1.0000 Uiso R . . . . . H412 H 0.6690 0.5932 0.3781 0.0169 1.0000 Uiso R . . . . . C42 C 0.9264(3) 0.4727(2) 0.3869(2) 0.0133 1.0000 Uani ...... C43 C 1.0330(3) 0.4433(2) 0.3370(2) 0.0128 1.0000 Uani ...... C44 C 1.0482(3) 0.4540(2) 0.2519(2) 0.0136 1.0000 Uani ...... H441 H 1.1204 0.4330 0.2193 0.0159 1.0000 Uiso R . . . . . S45 S 1.15040(7) 0.39463(6) 0.38387(5) 0.0130 1.0000 Uani ...... O46 O 1.1575(2) 0.4646(2) 0.42237(18) 0.0202 1.0000 Uani ...... O47 O 1.2519(2) 0.37717(19) 0.31556(17) 0.0172 1.0000 Uani ...... O48 O 1.1240(2) 0.30370(19) 0.44469(17) 0.0181 1.0000 Uani ...... H421 H 0.9177 0.4634 0.4444 0.0158 1.0000 Uiso R . . . . . H361 H 1.0494 0.5249 0.0919 0.0188 1.0000 Uiso R . . . . . H362 H 0.9159 0.5609 0.1010 0.0185 1.0000 Uiso R . . . . . H242 H 0.6811 0.3224 0.1151 0.0223 1.0000 Uiso R . . . . . H241 H 0.7460 0.2184 0.1075 0.0218 1.0000 Uiso R . . . . . H201 H 0.8115 0.1045 0.2339 0.0228 1.0000 Uiso R . . . . . H141 H 0.6223 0.1300 0.4627 0.0216 1.0000 Uiso R . . . . . H122 H 0.4400 0.2546 0.4686 0.0188 1.0000 Uiso R . . . . . H121 H 0.4401 0.3479 0.3924 0.0191 1.0000 Uiso R . . . . . H61 H 0.6854 0.4448 0.5727 0.0149 1.0000 Uiso R . . . . . O49 O 0.3225(2) 0.1653(2) 0.81735(17) 0.0185 1.0000 Uani ...... H491 H 0.2987 0.1617 0.8677 0.0280 1.0000 Uiso R . . . . . H492 H 0.3625 0.2075 0.7957 0.0280 1.0000 Uiso R . . . . . O50 O 0.6712(2) 0.4623(2) 0.79953(18) 0.0213 1.0000 Uani ...... H501 H 0.6931 0.5091 0.7626 0.0322 1.0000 Uiso R . . . . . H502 H 0.6623 0.4283 0.7751 0.0323 1.0000 Uiso R . . . . . O51 O 0.2843(2) 0.2282(2) 0.61944(18) 0.0202 1.0000 Uani ...... C52 C 0.1833(3) 0.2514(2) 0.6529(2) 0.0155 1.0000 Uani ...... N53 N 0.1451(3) 0.2425(2) 0.7393(2) 0.0146 1.0000 Uani ...... C54 C 0.0358(3) 0.2725(2) 0.7805(2) 0.0156 1.0000 Uani ...... N55 N 0.0103(3) 0.2618(2) 0.8620(2) 0.0184 1.0000 Uani ...... H551 H -0.0579 0.2819 0.8884 0.0221 1.0000 Uiso R . . . . . H552 H 0.0635 0.2408 0.8887 0.0221 1.0000 Uiso R . . . . . C56 C -0.0471(3) 0.3129(3) 0.7324(2) 0.0167 1.0000 Uani ...... C57 C -0.0128(3) 0.3184(3) 0.6499(2) 0.0185 1.0000 Uani ...... N58 N 0.0984(3) 0.2873(2) 0.6109(2) 0.0163 1.0000 Uani ...... H581 H 0.1179 0.2960 0.5571 0.0202 1.0000 Uiso R . . . . . H571 H -0.0664 0.3437 0.6183 0.0222 1.0000 Uiso R . . . . . H561 H -0.1230 0.3343 0.7577 0.0196 1.0000 Uiso R . . . . . H531 H 0.1950 0.2202 0.7672 0.0171 1.0000 Uiso R . . . . . O59 O 0.4299(3) 0.8806(2) 0.88440(19) 0.0269 1.0000 Uani ...... C60 C 0.4600(3) 0.9083(3) 0.8080(3) 0.0195 1.0000 Uani ...... N61 N 0.4173(3) 0.9968(2) 0.7636(2) 0.0207 1.0000 Uani ...... C62 C 0.4481(4) 1.0267(3) 0.6785(3) 0.0223 1.0000 Uani ...... C63 C 0.5259(3) 0.9700(3) 0.6319(3) 0.0211 1.0000 Uani ...... C64 C 0.5770(3) 0.8789(3) 0.6747(2) 0.0169 1.0000 Uani ...... N65 N 0.5412(3) 0.8514(2) 0.7595(2) 0.0194 1.0000 Uani ...... H651 H 0.5805 0.8010 0.7856 0.0231 1.0000 Uiso R . . . . . N66 N 0.6578(3) 0.8214(2) 0.6351(2) 0.0193 1.0000 Uani ...... H662 H 0.6864 0.7657 0.6624 0.0230 1.0000 Uiso R . . . . . H661 H 0.6844 0.8408 0.5824 0.0231 1.0000 Uiso R . . . . . H631 H 0.5460 0.9902 0.5738 0.0261 1.0000 Uiso R . . . . . H621 H 0.4142 1.0872 0.6519 0.0270 1.0000 Uiso R . . . . . H611 H 0.3741 1.0373 0.7913 0.0245 1.0000 Uiso R . . . . . O67 O 1.0774(3) -0.0031(2) 0.89558(19) 0.0239 1.0000 Uani ...... C68 C 0.9827(3) 0.0370(3) 0.8841(3) 0.0194 1.0000 Uani ...... N69 N 0.9660(3) 0.0670(2) 0.8044(2) 0.0186 1.0000 Uani ...... C70 C 0.8630(4) 0.1083(3) 0.7865(3) 0.0198 1.0000 Uani ...... N71 N 0.8568(3) 0.1290(3) 0.7092(2) 0.0233 1.0000 Uani ...... H711 H 0.7914 0.1523 0.6969 0.0280 1.0000 Uiso R . . . . . H712 H 0.9153 0.1117 0.6707 0.0283 1.0000 Uiso R . . . . . C72 C 0.7673(4) 0.1284(3) 0.8533(3) 0.0227 1.0000 Uani ...... C73 C 0.7828(4) 0.0998(3) 0.9314(3) 0.0240 1.0000 Uani ...... N74 N 0.8880(3) 0.0564(2) 0.9458(2) 0.0210 1.0000 Uani ...... H741 H 0.8929 0.0331 0.9967 0.0249 1.0000 Uiso R . . . . . H731 H 0.7205 0.1088 0.9773 0.0285 1.0000 Uiso R . . . . . H721 H 0.6962 0.1599 0.8432 0.0270 1.0000 Uiso R . . . . . H691 H 1.0250 0.0587 0.7631 0.0221 1.0000 Uiso R . . . . . O75 O 0.2186(3) 0.6453(2) 0.07916(18) 0.0234 1.0000 Uani ...... H751 H 0.2420 0.6120 0.1202 0.0349 1.0000 Uiso R . . . . . H752 H 0.2714 0.6734 0.0475 0.0350 1.0000 Uiso R . . . . . O76 O 0.4187(3) 0.3554(2) 0.9008(2) 0.0276 1.0000 Uani ...... H761 H 0.3671 0.3219 0.9306 0.0412 1.0000 Uiso R . . . . . H762 H 0.4360 0.3460 0.8551 0.0410 1.0000 Uiso R . . . . . O77 O 0.6777(3) 0.7147(2) 0.8474(2) 0.0321 1.0000 Uani ...... H771 H 0.6733 0.6577 0.8695 0.0482 1.0000 Uiso R . . . . . H772 H 0.6831 0.7352 0.8844 0.0480 1.0000 Uiso R . . . . . O78 O 0.2930(3) 0.4631(2) 0.0374(2) 0.0346 1.0000 Uani ...... H781 H 0.3441 0.4747 -0.0060 0.0512 1.0000 Uiso R . . . . . H782 H 0.2683 0.5139 0.0509 0.0514 1.0000 Uiso R . . . . . O79 O 0.5670(3) 0.3060(3) 0.0037(2) 0.0424 1.0000 Uani ...... H791 H 0.5683 0.2520 0.0358 0.0472 1.0000 Uiso R . . . . . H792 H 0.5234 0.3205 -0.0270 0.0472 1.0000 Uiso R . . . . . O80 O 0.5242(3) 0.4501(3) 0.0974(2) 0.0374 1.0000 Uani ...... H801 H 0.4760 0.4879 0.1203 0.0551 1.0000 Uiso R . . . . . H802 H 0.4923 0.4346 0.0699 0.0545 1.0000 Uiso R . . . . . O81 O 0.1208(6) 0.7929(5) 0.4655(4) 0.0336 0.6638 Uani . U . 1 1 . O82 O 0.0868(13) 0.8237(10) 0.4572(9) 0.0295 0.3362 Uani . U . 1 2 . C83 C 0.0701(4) 0.8058(3) 0.5345(3) 0.0244 1.0000 Uani ...... N84 N -0.0234(6) 0.8735(5) 0.5486(4) 0.0185 0.6638 Uani . U . 1 1 . N85 N -0.0294(13) 0.8555(11) 0.5817(8) 0.0195 0.3362 Uani . U . 1 2 . C86 C -0.0840(6) 0.8905(5) 0.6242(4) 0.0219 0.6638 Uani . U . 1 1 . H851 H -0.0865 0.8800 0.5592 0.0212 0.3362 Uiso R . . 1 2 . C87 C -0.0501(15) 0.8461(12) 0.6647(11) 0.0200 0.3362 Uani . U . 1 2 . N88 N -0.1366(10) 0.8982(8) 0.7038(7) 0.0263 0.3362 Uani . U . 1 2 . C89 C -0.0442(8) 0.8306(7) 0.6955(6) 0.0277 0.6638 Uani . U . 1 1 . H891 H -0.0814 0.8387 0.7492 0.0359 0.6638 Uiso R . . 1 1 . C90 C 0.0493(9) 0.7622(6) 0.6843(5) 0.0248 0.6638 Uani . U . 1 1 . C91 C 0.0282(19) 0.7782(15) 0.7074(12) 0.0252 0.3362 Uani . U . 1 2 . C92 C 0.1209(13) 0.7273(9) 0.6642(8) 0.0238 0.3362 Uani . U . 1 2 . H901 H 0.0753 0.7218 0.7305 0.0298 0.6638 Uiso R . . 1 1 . N93 N 0.1061(7) 0.7496(7) 0.6056(6) 0.0275 0.6638 Uani . U . 1 1 . N94 N 0.1398(15) 0.7423(15) 0.5810(13) 0.0270 0.3362 Uani . U . 1 2 . H931 H 0.1550 0.6976 0.6027 0.0302 0.6638 Uiso R . . 1 1 . H941 H 0.2012 0.7104 0.5550 0.0242 0.3362 Uiso R . . 1 2 . H921 H 0.1711 0.6808 0.6924 0.0280 0.3362 Uiso R . . 1 2 . H911 H 0.0192 0.7697 0.7645 0.0322 0.3362 Uiso R . . 1 2 . N95 N -0.1717(5) 0.9609(4) 0.6273(4) 0.0277 0.6638 Uani . U . 1 1 . H882 H -0.1968 0.9203 0.6848 0.0320 0.3362 Uiso R . . 1 2 . H951 H -0.2106 0.9722 0.6748 0.0600 0.6638 Uiso R . . 1 1 . H952 H -0.1904 0.9958 0.5819 0.0600 0.6638 Uiso R . . 1 1 . H881 H -0.1402 0.9016 0.7532 0.0320 0.3362 Uiso R . . 1 2 . H841 H -0.0487 0.9080 0.5055 0.0258 0.6638 Uiso R . . 1 1 . O96 O 0.6710(4) 0.9839(3) 0.7782(3) 0.0512 1.0000 Uani ...... H961 H 0.7138 0.9639 0.8106 0.0764 1.0000 Uiso R . . . . . H962 H 0.6386 1.0377 0.7837 0.0764 1.0000 Uiso R . . . . . O97 O 0.4986(7) 0.8884(6) 0.0535(5) 0.0450 0.5000 Uani ...... C98 C 0.500000(10) 1.000000(10) 0.000000(10) 0.0634 1.0000 Uani S . . . . . H985 H 0.5550 1.0249 0.0129 0.0960 0.5000 Uiso R . . . . . H984 H 0.5214 1.0037 -0.0591 0.0960 0.5000 Uiso R . . . . . H986 H 0.5756 0.9631 -0.0151 0.0960 0.5000 Uiso R . . . . . H971 H 0.5555 0.8546 0.0314 0.0680 0.5000 Uiso R . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0178(4) 0.0134(4) 0.0123(4) -0.0018(3) -0.0043(3) -0.0007(3) O2 0.0342(16) 0.0242(15) 0.0164(14) -0.0051(11) -0.0109(12) -0.0080(12) O3 0.0230(14) 0.0213(14) 0.0131(13) -0.0026(10) -0.0001(10) -0.0003(11) O4 0.0265(14) 0.0125(13) 0.0174(14) -0.0007(10) -0.0080(11) 0.0007(10) C5 0.0107(15) 0.0122(16) 0.0154(17) -0.0050(13) -0.0006(12) 0.0035(12) C6 0.0128(15) 0.0133(16) 0.0121(16) -0.0049(13) -0.0035(12) 0.0020(12) C7 0.0122(15) 0.0097(15) 0.0125(16) -0.0049(12) -0.0008(12) 0.0022(12) C8 0.0117(15) 0.0139(16) 0.0130(17) -0.0066(13) -0.0028(12) 0.0029(12) O9 0.0209(13) 0.0195(13) 0.0100(12) -0.0016(10) -0.0035(10) -0.0055(10) C10 0.0113(15) 0.0122(16) 0.0188(18) -0.0067(13) -0.0011(13) 0.0016(12) C11 0.0125(15) 0.0108(16) 0.0148(17) -0.0044(13) -0.0007(12) 0.0020(12) C12 0.0139(16) 0.0173(17) 0.0158(18) -0.0067(14) -0.0009(13) -0.0019(13) C13 0.0134(16) 0.0176(17) 0.0191(18) -0.0105(14) -0.0018(13) -0.0033(13) C14 0.0222(18) 0.0164(17) 0.0147(18) -0.0043(14) -0.0011(14) -0.0062(14) C15 0.0210(18) 0.0130(17) 0.024(2) -0.0038(14) -0.0051(15) -0.0029(14) S16 0.0227(5) 0.0127(4) 0.0277(5) -0.0046(4) -0.0021(4) -0.0020(3) O17 0.0306(16) 0.0222(15) 0.0217(16) 0.0013(12) -0.0002(12) -0.0008(12) O18 0.088(3) 0.0153(16) 0.036(2) 0.0018(15) 0.031(2) 0.0194(18) O19 0.067(3) 0.0227(18) 0.138(5) -0.008(2) -0.077(3) -0.0036(18) C20 0.0178(17) 0.0159(17) 0.023(2) -0.0113(15) -0.0004(14) -0.0008(14) C21 0.0150(16) 0.0196(18) 0.0175(18) -0.0088(14) -0.0024(13) -0.0029(13) C22 0.0130(16) 0.0192(18) 0.0192(19) -0.0092(14) -0.0043(13) -0.0015(13) O23 0.0192(13) 0.0220(14) 0.0149(13) -0.0051(10) -0.0050(10) 0.0018(11) C24 0.0197(18) 0.0206(18) 0.0166(19) -0.0097(14) -0.0024(14) -0.0014(14) C25 0.0201(18) 0.0186(18) 0.0101(16) -0.0050(13) -0.0037(13) -0.0022(14) C26 0.0152(17) 0.0185(18) 0.0124(17) -0.0048(13) -0.0026(13) 0.0028(13) O27 0.0162(13) 0.0214(14) 0.0232(15) -0.0136(11) -0.0033(10) 0.0030(10) C28 0.0180(17) 0.0152(17) 0.0080(16) -0.0040(13) -0.0006(12) -0.0001(13) C29 0.0155(16) 0.0178(17) 0.0097(16) -0.0034(13) -0.0006(12) -0.0031(13) C30 0.0218(18) 0.0153(17) 0.0108(17) -0.0042(13) -0.0020(13) 0.0003(14) C31 0.0172(17) 0.0163(17) 0.0118(17) -0.0068(13) 0.0006(13) -0.0017(13) S32 0.0162(4) 0.0149(4) 0.0118(4) -0.0043(3) -0.0014(3) 0.0014(3) O33 0.0151(13) 0.0199(14) 0.0237(15) -0.0075(11) 0.0024(10) -0.0034(10) O34 0.0224(14) 0.0227(14) 0.0159(14) -0.0098(11) -0.0039(11) 0.0034(11) O35 0.0262(15) 0.0186(14) 0.0171(14) 0.0003(11) -0.0069(11) 0.0003(11) C36 0.0159(17) 0.0167(17) 0.0114(17) -0.0013(13) -0.0042(13) 0.0009(13) C37 0.0162(16) 0.0078(15) 0.0129(17) -0.0007(12) -0.0008(12) -0.0027(12) C38 0.0132(16) 0.0091(15) 0.0133(17) -0.0010(12) -0.0035(12) -0.0003(12) O39 0.0121(12) 0.0163(12) 0.0139(12) -0.0036(10) -0.0029(9) 0.0030(9) C40 0.0150(16) 0.0103(16) 0.0150(17) -0.0028(13) -0.0004(13) -0.0013(12) C41 0.0133(16) 0.0122(16) 0.0134(17) -0.0045(13) -0.0010(12) 0.0015(12) C42 0.0188(17) 0.0080(15) 0.0118(16) -0.0027(12) -0.0005(13) -0.0040(12) C43 0.0118(15) 0.0118(16) 0.0142(17) -0.0019(12) -0.0048(12) -0.0011(12) C44 0.0129(16) 0.0122(16) 0.0144(17) -0.0054(13) -0.0015(12) 0.0003(12) S45 0.0127(4) 0.0127(4) 0.0122(4) -0.0037(3) -0.0032(3) 0.0009(3) O46 0.0216(14) 0.0188(13) 0.0254(15) -0.0098(11) -0.0121(11) 0.0006(11) O47 0.0137(12) 0.0169(13) 0.0175(13) -0.0046(10) -0.0022(10) 0.0017(10) O48 0.0206(13) 0.0174(13) 0.0139(13) -0.0014(10) -0.0041(10) -0.0029(10) O49 0.0211(13) 0.0209(14) 0.0130(13) -0.0079(10) -0.0014(10) -0.0020(10) O50 0.0248(14) 0.0195(14) 0.0180(14) -0.0052(11) -0.0040(11) -0.0024(11) O51 0.0179(13) 0.0183(13) 0.0196(14) -0.0065(11) 0.0005(10) 0.0007(10) C52 0.0215(18) 0.0069(15) 0.0152(17) -0.0021(12) -0.0028(13) -0.0005(13) N53 0.0162(15) 0.0118(14) 0.0143(15) -0.0034(11) -0.0046(11) 0.0012(11) C54 0.0176(17) 0.0083(15) 0.0181(18) -0.0031(13) -0.0024(13) -0.0004(12) N55 0.0164(15) 0.0197(16) 0.0160(16) -0.0056(12) -0.0031(12) 0.0021(12) C56 0.0158(17) 0.0135(17) 0.0178(18) -0.0039(13) -0.0038(13) 0.0019(13) C57 0.0197(18) 0.0144(17) 0.0205(19) -0.0033(14) -0.0076(14) 0.0002(13) N58 0.0199(15) 0.0137(14) 0.0121(15) -0.0030(11) -0.0024(11) 0.0004(11) O59 0.0330(17) 0.0257(15) 0.0180(15) -0.0081(12) -0.0012(12) -0.0014(12) C60 0.0202(18) 0.0183(18) 0.022(2) -0.0094(15) -0.0053(14) -0.0011(14) N61 0.0202(16) 0.0188(16) 0.0225(17) -0.0112(13) -0.0032(13) 0.0025(12) C62 0.0235(19) 0.0144(18) 0.026(2) -0.0029(15) -0.0081(16) 0.0006(14) C63 0.0232(19) 0.0176(18) 0.0183(19) -0.0032(14) -0.0055(15) 0.0025(14) C64 0.0165(17) 0.0152(17) 0.0197(19) -0.0051(14) -0.0062(14) -0.0011(13) N65 0.0236(17) 0.0159(15) 0.0171(16) -0.0059(12) -0.0058(13) 0.0026(12) N66 0.0184(15) 0.0171(15) 0.0189(16) -0.0055(12) -0.0030(12) 0.0016(12) O67 0.0240(15) 0.0236(15) 0.0228(15) -0.0072(12) -0.0087(11) 0.0034(11) C68 0.0242(19) 0.0133(17) 0.0188(19) -0.0039(14) -0.0051(15) -0.0007(14) N69 0.0196(16) 0.0175(16) 0.0176(16) -0.0050(12) -0.0028(12) -0.0031(12) C70 0.0246(19) 0.0142(17) 0.021(2) -0.0040(14) -0.0078(15) -0.0027(14) N71 0.0256(18) 0.0275(18) 0.0170(17) -0.0071(14) -0.0071(13) -0.0011(14) C72 0.0212(19) 0.0190(19) 0.023(2) -0.0012(15) -0.0064(15) -0.0002(15) C73 0.026(2) 0.0199(19) 0.022(2) -0.0037(15) -0.0045(16) -0.0011(15) N74 0.0240(17) 0.0195(16) 0.0162(16) -0.0037(13) -0.0053(13) 0.0007(13) O75 0.0242(14) 0.0267(15) 0.0156(14) -0.0043(11) -0.0038(11) -0.0010(12) O76 0.0324(17) 0.0308(16) 0.0204(15) -0.0087(12) -0.0028(12) -0.0093(13) O77 0.048(2) 0.0232(16) 0.0225(16) -0.0058(12) -0.0158(14) 0.0073(14) O78 0.0383(19) 0.0319(18) 0.0299(18) -0.0087(14) -0.0032(14) -0.0056(14) O79 0.040(2) 0.049(2) 0.037(2) 0.0095(17) -0.0202(16) -0.0170(17) O80 0.0357(19) 0.046(2) 0.0260(18) -0.0151(15) -0.0065(14) 0.0061(15) O81 0.038(4) 0.028(4) 0.021(3) 0.001(3) -0.006(3) 0.004(3) O82 0.035(6) 0.029(6) 0.015(4) 0.000(4) -0.010(4) 0.007(4) C83 0.030(2) 0.0184(19) 0.023(2) -0.0001(15) -0.0069(17) -0.0072(16) N84 0.022(2) 0.013(3) 0.018(4) 0.004(3) -0.006(3) -0.008(2) N85 0.025(4) 0.009(5) 0.015(6) 0.007(5) -0.006(5) 0.000(3) C86 0.031(3) 0.018(3) 0.022(3) -0.005(2) -0.009(2) -0.011(2) C87 0.030(5) 0.017(5) 0.018(5) -0.007(4) -0.010(4) -0.006(4) N88 0.029(4) 0.019(4) 0.031(4) -0.009(3) -0.007(3) -0.003(3) C89 0.037(4) 0.028(4) 0.021(4) -0.005(3) -0.008(3) -0.012(3) C90 0.038(5) 0.016(4) 0.023(4) 0.002(3) -0.016(4) -0.009(3) C91 0.036(5) 0.026(5) 0.018(5) -0.010(4) -0.005(5) -0.010(4) C92 0.036(5) 0.016(5) 0.019(5) 0.003(4) -0.015(4) -0.005(4) N93 0.028(5) 0.017(2) 0.037(6) -0.004(3) -0.016(4) 0.002(3) N94 0.027(5) 0.017(3) 0.037(6) -0.004(3) -0.016(4) 0.002(4) N95 0.030(3) 0.025(3) 0.029(3) -0.009(2) -0.004(2) -0.008(2) O96 0.053(3) 0.046(2) 0.059(3) -0.013(2) -0.024(2) -0.0042(19) O97 0.036(4) 0.048(5) 0.042(5) -0.015(4) 0.000(3) 0.001(3) C98 0.053(5) 0.092(8) 0.066(7) -0.053(6) -0.003(5) -0.022(5)

_refine_ls_extinction_coef 43(9) _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 1.434(8) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 . O2 . 1.443(3) yes S1 . O3 . 1.469(3) yes S1 . O4 . 1.471(3) yes S1 . C5 . 1.765(4) yes C5 . C6 . 1.391(5) yes C5 . C11 . 1.382(5) yes C6 . C7 . 1.397(5) yes C6 . H61 . 0.927 no C7 . C8 . 1.402(5) yes C7 . C41 . 1.512(5) yes C8 . O9 . 1.353(4) yes C8 . C10 . 1.402(5) yes O9 . H91 . 0.814 no C10 . C11 . 1.386(5) yes C10 . C12 . 1.509(5) yes C11 . H111 . 0.932 no C12 . C13 . 1.523(5) yes C12 . H122 . 0.976 no C12 . H121 . 0.969 no C13 . C14 . 1.382(5) yes C13 . C22 . 1.405(5) yes C14 . C15 . 1.402(5) yes C14 . H141 . 0.930 no C15 . S16 . 1.769(4) yes C15 . C20 . 1.386(6) yes S16 . O17 . 1.432(3) yes S16 . O18 . 1.446(4) yes S16 . O19 . 1.458(4) yes C20 . C21 . 1.392(5) yes C20 . H201 . 0.932 no C21 . C22 . 1.414(5) yes C21 . C24 . 1.524(5) yes C22 . O23 . 1.363(5) yes O23 . H231 . 0.817 no C24 . C25 . 1.516(5) yes C24 . H242 . 0.970 no C24 . H241 . 0.969 no C25 . C26 . 1.400(5) yes C25 . C31 . 1.384(5) yes C26 . O27 . 1.360(4) yes C26 . C28 . 1.403(5) yes O27 . H271 . 0.809 no C28 . C29 . 1.403(5) yes C28 . C36 . 1.517(5) yes C29 . C30 . 1.382(5) yes C29 . H291 . 0.932 no C30 . C31 . 1.400(5) yes C30 . S32 . 1.771(4) yes C31 . H311 . 0.946 no S32 . O33 . 1.463(3) yes S32 . O34 . 1.456(3) yes S32 . O35 . 1.456(3) yes C36 . C37 . 1.520(5) yes C36 . H361 . 0.981 no C36 . H362 . 0.968 no C37 . C38 . 1.412(5) yes C37 . C44 . 1.399(5) yes C38 . O39 . 1.374(4) yes C38 . C40 . 1.399(5) yes O39 . H391 . 0.819 no C40 . C41 . 1.522(5) yes C40 . C42 . 1.398(5) yes C41 . H411 . 0.976 no C41 . H412 . 0.966 no C42 . C43 . 1.388(5) yes C42 . H421 . 0.938 no C43 . C44 . 1.391(5) yes C43 . S45 . 1.775(4) yes C44 . H441 . 0.935 no S45 . O46 . 1.438(3) yes S45 . O47 . 1.469(3) yes S45 . O48 . 1.467(3) yes O49 . H491 . 0.818 no O49 . H492 . 0.821 no O50 . H501 . 0.820 no O50 . H502 . 0.802 no O51 . C52 . 1.219(5) yes C52 . N53 . 1.397(5) yes C52 . N58 . 1.371(5) yes N53 . C54 . 1.359(5) yes N53 . H531 . 0.842 no C54 . N55 . 1.315(5) yes C54 . C56 . 1.423(5) yes N55 . H551 . 0.857 no N55 . H552 . 0.863 no C56 . C57 . 1.341(6) yes C56 . H561 . 0.929 no C57 . N58 . 1.369(5) yes C57 . H571 . 0.926 no N58 . H581 . 0.861 no O59 . C60 . 1.220(5) yes C60 . N61 . 1.368(5) yes C60 . N65 . 1.391(5) yes N61 . C62 . 1.356(5) yes N61 . H611 . 0.862 no C62 . C63 . 1.354(6) yes C62 . H621 . 0.931 no C63 . C64 . 1.420(5) yes C63 . H631 . 0.926 no C64 . N65 . 1.352(5) yes C64 . N66 . 1.313(5) yes N65 . H651 . 0.863 no N66 . H662 . 0.864 no N66 . H661 . 0.848 no O67 . C68 . 1.224(5) yes C68 . N69 . 1.377(5) yes C68 . N74 . 1.360(5) yes N69 . C70 . 1.358(5) yes N69 . H691 . 0.865 no C70 . N71 . 1.301(5) yes C70 . C72 . 1.424(6) yes N71 . H711 . 0.863 no N71 . H712 . 0.867 no C72 . C73 . 1.346(6) yes C72 . H721 . 0.931 no C73 . N74 . 1.365(5) yes C73 . H731 . 0.939 no N74 . H741 . 0.857 no O75 . H751 . 0.819 no O75 . H752 . 0.821 no O76 . H761 . 0.847 no O76 . H762 . 0.803 no O77 . H771 . 0.820 no O77 . H772 . 0.819 no O78 . H781 . 0.821 no O78 . H782 . 0.820 no O79 . H791 . 0.820 no O79 . H792 . 0.819 no O80 . H801 . 0.810 no O80 . H802 . 0.820 no O81 . C83 . 1.217(8) yes O82 . C83 . 1.241(14) yes C83 . N84 . 1.348(9) yes C83 . N93 . 1.386(11) yes C83 . N85 . 1.427(17) yes C83 . N94 . 1.35(2) yes N84 . C86 . 1.360(10) yes N84 . H841 . 0.862 no N85 . H851 . 0.860 no N85 . C87 . 1.35(2) yes C86 . C89 . 1.424(10) yes C86 . N95 . 1.309(9) yes C87 . N88 . 1.29(2) yes C87 . C91 . 1.41(3) yes N88 . H882 . 0.859 no N88 . H881 . 0.862 no C89 . H891 . 0.934 no C89 . C90 . 1.346(14) yes C90 . H901 . 0.931 no C90 . N93 . 1.376(12) yes C91 . C92 . 1.36(2) yes C91 . H911 . 0.931 no C92 . N94 . 1.34(2) yes C92 . H921 . 0.931 no N93 . H931 . 0.860 no N94 . H941 . 0.867 no N95 . H951 . 0.860 no N95 . H952 . 0.860 no O96 . H961 . 0.830 no O96 . H962 . 0.821 no O97 . C98 . 1.627(8) yes O97 . H971 . 0.821 no C98 . H986 2_675 0.965 no C98 . H985 2_675 0.964 no C98 . H984 2_675 0.963 no C98 . H985 . 0.964 no C98 . H984 . 0.963 no C98 . H986 . 0.965 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O2 . S1 . O3 . 113.08(18) yes O2 . S1 . O4 . 112.58(17) yes O3 . S1 . O4 . 110.90(17) yes O2 . S1 . C5 . 107.23(17) yes O3 . S1 . C5 . 106.86(16) yes O4 . S1 . C5 . 105.67(16) yes S1 . C5 . C6 . 122.0(3) yes S1 . C5 . C11 . 117.5(3) yes C6 . C5 . C11 . 120.6(3) yes C5 . C6 . C7 . 119.9(3) yes C5 . C6 . H61 . 119.9 no C7 . C6 . H61 . 120.3 no C6 . C7 . C8 . 118.9(3) yes C6 . C7 . C41 . 120.8(3) yes C8 . C7 . C41 . 120.3(3) yes C7 . C8 . O9 . 116.1(3) yes C7 . C8 . C10 . 121.1(3) yes O9 . C8 . C10 . 122.8(3) yes C8 . O9 . H91 . 117.3 no C8 . C10 . C11 . 118.6(3) yes C8 . C10 . C12 . 121.9(3) yes C11 . C10 . C12 . 119.5(3) yes C10 . C11 . C5 . 120.9(3) yes C10 . C11 . H111 . 119.6 no C5 . C11 . H111 . 119.4 no C10 . C12 . C13 . 110.2(3) yes C10 . C12 . H122 . 109.4 no C13 . C12 . H122 . 108.1 no C10 . C12 . H121 . 110.6 no C13 . C12 . H121 . 109.4 no H122 . C12 . H121 . 109.1 no C12 . C13 . C14 . 119.8(3) yes C12 . C13 . C22 . 120.8(3) yes C14 . C13 . C22 . 119.3(3) yes C13 . C14 . C15 . 120.6(4) yes C13 . C14 . H141 . 120.3 no C15 . C14 . H141 . 119.1 no C14 . C15 . S16 . 118.7(3) yes C14 . C15 . C20 . 119.7(4) yes S16 . C15 . C20 . 121.6(3) yes C15 . S16 . O17 . 107.01(19) yes C15 . S16 . O18 . 107.1(2) yes O17 . S16 . O18 . 113.3(2) yes C15 . S16 . O19 . 105.2(2) yes O17 . S16 . O19 . 109.7(3) yes O18 . S16 . O19 . 113.8(3) yes C15 . C20 . C21 . 121.4(4) yes C15 . C20 . H201 . 119.1 no C21 . C20 . H201 . 119.5 no C20 . C21 . C22 . 118.2(4) yes C20 . C21 . C24 . 118.8(3) yes C22 . C21 . C24 . 122.9(3) yes C21 . C22 . C13 . 120.8(3) yes C21 . C22 . O23 . 124.2(3) yes C13 . C22 . O23 . 115.0(3) yes C22 . O23 . H231 . 111.7 no C21 . C24 . C25 . 110.4(3) yes C21 . C24 . H242 . 110.1 no C25 . C24 . H242 . 109.1 no C21 . C24 . H241 . 109.0 no C25 . C24 . H241 . 108.9 no H242 . C24 . H241 . 109.3 no C24 . C25 . C26 . 120.9(3) yes C24 . C25 . C31 . 119.8(3) yes C26 . C25 . C31 . 119.1(3) yes C25 . C26 . O27 . 115.5(3) yes C25 . C26 . C28 . 121.3(3) yes O27 . C26 . C28 . 123.2(3) yes C26 . O27 . H271 . 123.7 no C26 . C28 . C29 . 118.4(3) yes C26 . C28 . C36 . 121.5(3) yes C29 . C28 . C36 . 119.9(3) yes C28 . C29 . C30 . 120.3(3) yes C28 . C29 . H291 . 119.8 no C30 . C29 . H291 . 119.9 no C29 . C30 . C31 . 120.7(3) yes C29 . C30 . S32 . 122.0(3) yes C31 . C30 . S32 . 117.0(3) yes C30 . C31 . C25 . 120.1(3) yes C30 . C31 . H311 . 120.1 no C25 . C31 . H311 . 119.8 no C30 . S32 . O33 . 107.54(18) yes C30 . S32 . O34 . 105.65(17) yes O33 . S32 . O34 . 112.08(17) yes C30 . S32 . O35 . 106.05(17) yes O33 . S32 . O35 . 112.37(18) yes O34 . S32 . O35 . 112.60(18) yes C28 . C36 . C37 . 111.8(3) yes C28 . C36 . H361 . 108.2 no C37 . C36 . H361 . 108.2 no C28 . C36 . H362 . 109.9 no C37 . C36 . H362 . 109.9 no H361 . C36 . H362 . 108.7 no C36 . C37 . C38 . 121.6(3) yes C36 . C37 . C44 . 119.8(3) yes C38 . C37 . C44 . 118.6(3) yes C37 . C38 . O39 . 115.4(3) yes C37 . C38 . C40 . 121.7(3) yes O39 . C38 . C40 . 122.9(3) yes C38 . O39 . H391 . 114.6 no C38 . C40 . C41 . 123.6(3) yes C38 . C40 . C42 . 118.0(3) yes C41 . C40 . C42 . 118.4(3) yes C40 . C41 . C7 . 112.7(3) yes C40 . C41 . H411 . 107.8 no C7 . C41 . H411 . 108.0 no C40 . C41 . H412 . 109.2 no C7 . C41 . H412 . 109.8 no H411 . C41 . H412 . 109.2 no C40 . C42 . C43 . 120.8(3) yes C40 . C42 . H421 . 119.8 no C43 . C42 . H421 . 119.3 no C42 . C43 . C44 . 120.9(3) yes C42 . C43 . S45 . 118.4(3) yes C44 . C43 . S45 . 120.8(3) yes C37 . C44 . C43 . 119.8(3) yes C37 . C44 . H441 . 120.4 no C43 . C44 . H441 . 119.8 no C43 . S45 . O46 . 106.57(16) yes C43 . S45 . O47 . 106.12(16) yes O46 . S45 . O47 . 113.54(17) yes C43 . S45 . O48 . 106.24(16) yes O46 . S45 . O48 . 113.13(17) yes O47 . S45 . O48 . 110.63(16) yes H491 . O49 . H492 . 108.2 no H501 . O50 . H502 . 105.0 no O51 . C52 . N53 . 121.3(3) yes O51 . C52 . N58 . 124.1(3) yes N53 . C52 . N58 . 114.5(3) yes C52 . N53 . C54 . 125.0(3) yes C52 . N53 . H531 . 117.0 no C54 . N53 . H531 . 117.8 no N53 . C54 . N55 . 119.6(3) yes N53 . C54 . C56 . 117.5(3) yes N55 . C54 . C56 . 123.0(3) yes C54 . N55 . H551 . 120.3 no C54 . N55 . H552 . 120.5 no H551 . N55 . H552 . 118.7 no C54 . C56 . C57 . 118.3(3) yes C54 . C56 . H561 . 120.7 no C57 . C56 . H561 . 121.0 no C56 . C57 . N58 . 122.4(4) yes C56 . C57 . H571 . 118.9 no N58 . C57 . H571 . 118.7 no C52 . N58 . C57 . 122.2(3) yes C52 . N58 . H581 . 118.2 no C57 . N58 . H581 . 119.3 no O59 . C60 . N61 . 123.0(4) yes O59 . C60 . N65 . 121.9(4) yes N61 . C60 . N65 . 115.1(4) yes C60 . N61 . C62 . 123.1(3) yes C60 . N61 . H611 . 118.0 no C62 . N61 . H611 . 118.6 no N61 . C62 . C63 . 121.3(4) yes N61 . C62 . H621 . 119.0 no C63 . C62 . H621 . 119.8 no C62 . C63 . C64 . 118.1(4) yes C62 . C63 . H631 . 121.1 no C64 . C63 . H631 . 120.7 no C63 . C64 . N65 . 118.3(3) yes C63 . C64 . N66 . 122.4(4) yes N65 . C64 . N66 . 119.3(3) yes C60 . N65 . C64 . 124.0(3) yes C60 . N65 . H651 . 117.2 no C64 . N65 . H651 . 117.6 no C64 . N66 . H662 . 120.8 no C64 . N66 . H661 . 119.2 no H662 . N66 . H661 . 120.0 no O67 . C68 . N69 . 120.4(4) yes O67 . C68 . N74 . 124.5(4) yes N69 . C68 . N74 . 115.0(3) yes C68 . N69 . C70 . 124.3(4) yes C68 . N69 . H691 . 117.8 no C70 . N69 . H691 . 117.9 no N69 . C70 . N71 . 118.7(4) yes N69 . C70 . C72 . 118.2(4) yes N71 . C70 . C72 . 123.2(4) yes C70 . N71 . H711 . 120.1 no C70 . N71 . H712 . 120.7 no H711 . N71 . H712 . 118.5 no C70 . C72 . C73 . 117.8(4) yes C70 . C72 . H721 . 120.9 no C73 . C72 . H721 . 121.3 no C72 . C73 . N74 . 121.2(4) yes C72 . C73 . H731 . 120.0 no N74 . C73 . H731 . 118.8 no C73 . N74 . C68 . 123.4(4) yes C73 . N74 . H741 . 118.5 no C68 . N74 . H741 . 117.6 no H751 . O75 . H752 . 105.6 no H761 . O76 . H762 . 105.8 no H771 . O77 . H772 . 105.0 no H781 . O78 . H782 . 105.7 no H791 . O79 . H792 . 115.7 no H801 . O80 . H802 . 105.5 no O81 . C83 . N84 . 124.0(5) yes O81 . C83 . N93 . 121.0(5) yes N84 . C83 . N93 . 114.9(5) yes O82 . C83 . N85 . 119.6(8) yes O82 . C83 . N94 . 125.9(10) yes N85 . C83 . N94 . 114.5(9) yes C83 . N84 . C86 . 126.5(6) yes C83 . N84 . H841 . 116.5 no C86 . N84 . H841 . 116.9 no C83 . N85 . H851 . 116.9 no C83 . N85 . C87 . 123.7(13) yes H851 . N85 . C87 . 117.3 no N84 . C86 . C89 . 116.5(7) yes N84 . C86 . N95 . 119.2(6) yes C89 . C86 . N95 . 124.3(7) yes N85 . C87 . N88 . 121.8(16) yes N85 . C87 . C91 . 117.3(16) yes N88 . C87 . C91 . 121.0(15) yes C87 . N88 . H882 . 119.2 no C87 . N88 . H881 . 120.8 no H882 . N88 . H881 . 118.9 no C86 . C89 . H891 . 120.9 no C86 . C89 . C90 . 119.0(8) yes H891 . C89 . C90 . 120.1 no C89 . C90 . H901 . 119.8 no C89 . C90 . N93 . 121.1(9) yes H901 . C90 . N93 . 119.2 no C87 . C91 . C92 . 119.8(16) yes C87 . C91 . H911 . 121.0 no C92 . C91 . H911 . 119.1 no C91 . C92 . N94 . 120.4(15) yes C91 . C92 . H921 . 120.1 no N94 . C92 . H921 . 119.4 no C83 . N93 . C90 . 122.0(7) yes C83 . N93 . H931 . 119.1 no C90 . N93 . H931 . 117.4 no C83 . N94 . C92 . 124.2(14) yes C83 . N94 . H941 . 117.6 no C92 . N94 . H941 . 118.1 no C86 . N95 . H951 . 120.0 no C86 . N95 . H952 . 120.0 no H951 . N95 . H952 . 120.0 no H961 . O96 . H962 . 105.6 no C98 . O97 . H971 . 109.1 no O97 . C98 . O97 2_675 179.993 yes O97 . C98 . H986 2_675 109.2 no O97 2_675 C98 . H986 2_675 70.8 no O97 . C98 . H985 2_675 70.7 no O97 2_675 C98 . H985 2_675 109.3 no H986 2_675 C98 . H985 2_675 70.3 no O97 . C98 . H984 2_675 70.6 no O97 2_675 C98 . H984 2_675 109.4 no H986 2_675 C98 . H984 2_675 70.2 no H985 2_675 C98 . H984 2_675 109.6 no O97 . C98 . H985 . 109.3 no O97 2_675 C98 . H985 . 70.7 no H986 2_675 C98 . H985 . 109.7 no H985 2_675 C98 . H985 . 180.0 no H984 2_675 C98 . H985 . 70.4 no O97 . C98 . H984 . 109.4 no O97 2_675 C98 . H984 . 70.6 no H986 2_675 C98 . H984 . 109.8 no H985 2_675 C98 . H984 . 70.4 no H984 2_675 C98 . H984 . 180.0 no O97 . C98 . H986 . 70.8 no O97 2_675 C98 . H986 . 109.2 no H986 2_675 C98 . H986 . 180.0 no H985 2_675 C98 . H986 . 109.7 no H984 2_675 C98 . H986 . 109.8 no H985 . C98 . H984 . 109.6 no H985 . C98 . H986 . 70.3 no H984 . C98 . H986 . 70.2 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag O9 . H91 . O23 . 150.00 0.814 2.038 2.774(7) yes O23 . H231 . O80 . 149.00 0.817 1.915 2.649(7) yes O27 . H271 . O39 . 162.00 0.809 1.993 2.773(7) yes C29 . H291 . O78 1_655 163.68(12) 0.932 2.468 3.373(7) yes O39 . H391 . O3 2_666 139.09(10) 0.819 2.190 2.860(7) yes O39 . H391 . O9 . 123.00 0.819 2.261 2.797(7) yes C24 . H242 . O80 . 168.00 0.970 2.376 3.332(7) yes O49 . H491 . O34 1_456 151.77(12) 0.818 1.956 2.704(7) yes O49 . H492 . O3 . 179.85(11) 0.821 2.003 2.824(7) yes O50 . H501 . O47 2_766 174.24(12) 0.820 1.928 2.744(7) yes O50 . H502 . O2 . 172.00 0.802 1.957 2.754(7) yes N55 . H551 . O75 2_566 164.77(12) 0.857 2.018 2.853(7) yes N55 . H552 . O34 1_456 165.97(12) 0.863 2.160 3.004(7) yes N58 . H581 . O48 1_455 164.96(13) 0.861 1.897 2.738(7) yes N53 . H531 . O49 . 172.00 0.842 1.923 2.760(7) yes N65 . H651 . O77 . 166.00 0.863 1.848 2.694(7) yes N66 . H662 . O47 2_766 156.39(13) 0.864 2.026 2.839(7) yes N66 . H661 . O17 1_565 158.08(12) 0.848 2.120 2.924(7) yes C63 . H631 . O17 1_565 134.34(11) 0.926 2.505 3.221(7) yes C62 . H621 . O51 1_565 163.20(12) 0.931 2.333 3.236(7) yes N61 . H611 . O49 1_565 154.93(13) 0.862 2.000 2.805(7) yes N71 . H711 . O4 . 162.00 0.863 2.013 2.846(7) yes N74 . H741 . O67 2_757 167.43(14) 0.857 1.910 2.752(7) yes C73 . H731 . O59 2_667 171.82(12) 0.939 2.561 3.493(7) yes N69 . H691 . O18 2_756 169.96(18) 0.865 1.834 2.689(7) yes O75 . H751 . O50 2_666 167.72(12) 0.819 1.920 2.726(7) yes O75 . H752 . O79 2_665 156.75(14) 0.821 1.984 2.757(7) yes O76 . H761 . O33 1_456 160.86(13) 0.847 1.960 2.774(7) yes O76 . H762 . O3 . 171.00 0.803 2.088 2.884(7) yes O77 . H771 . O78 2_666 147.79(14) 0.820 2.053 2.782(7) yes O77 . H772 . O33 2_766 171.92(12) 0.819 2.028 2.841(7) yes O78 . H781 . O80 2_665 156.90(13) 0.821 2.148 2.920(7) yes O78 . H782 . O75 . 175.00 0.820 2.065 2.883(7) yes O79 . H791 . O59 2_666 179.36(14) 0.820 2.018 2.838(7) yes O79 . H792 . O76 1_554 179.41(15) 0.819 1.949 2.769(7) yes O80 . H801 . O50 2_666 158.70(14) 0.810 2.052 2.822(7) yes O80 . H802 . O79 . 126.00 0.820 2.385 2.939(7) yes N85 . H851 . O19 1_465 138.2(4) 0.860 2.387 3.082(7) yes C86 . H851 . O19 1_465 122.5(11) 1.198 2.387 3.195(7) yes C86 . H851 . O82 . 123.3(11) 1.198 2.474 3.288(7) yes C89 . H891 . O35 2_666 167.9(2) 0.934 2.586 3.504(7) yes C92 . H931 . O81 . 123.2(9) 1.200 2.458 3.272(7) yes N95 . H951 . O96 1_455 165.1(2) 0.860 1.958 2.798(7) yes N95 . H952 . O19 1_465 140.33(19) 0.860 2.170 2.884(7) yes N88 . H881 . O35 2_666 169.0(3) 0.862 2.144 2.995(7) yes N84 . H841 . O19 1_465 155.1(3) 0.862 1.846 2.653(7) yes O96 . H961 . O35 2_766 171.77(15) 0.830 1.986 2.810(7) yes O96 . H962 . O4 1_565 138.99(14) 0.821 2.192 2.862(7) yes O97 . H971 . O33 2_765 174.4(2) 0.821 2.176 2.994(7) yes

_iucr_refine_instruction_details_constraints ; # # Punched on 30/03/12 at 11:44:50 # #LIST 12 BLOCK SCALE X'S, U'S CONT EXTPARAM RIDE C ( 6,X'S) H ( 61,X'S) RIDE O ( 9,X'S) H ( 91,X'S) RIDE C ( 11,X'S) H ( 111,X'S) RIDE C ( 12,X'S) H ( 122,X'S) H ( 121,X'S) RIDE C ( 14,X'S) H ( 141,X'S) RIDE C ( 20,X'S) H ( 201,X'S) RIDE O ( 23,X'S) H ( 231,X'S) RIDE C ( 24,X'S) H ( 242,X'S) H ( 241,X'S) RIDE O ( 27,X'S) H ( 271,X'S) RIDE C ( 29,X'S) H ( 291,X'S) RIDE C ( 31,X'S) H ( 311,X'S) RIDE C ( 36,X'S) H ( 361,X'S) H ( 362,X'S) RIDE O ( 39,X'S) H ( 391,X'S) RIDE C ( 41,X'S) H ( 411,X'S) H ( 412,X'S) RIDE C ( 42,X'S) H ( 421,X'S) RIDE C ( 44,X'S) H ( 441,X'S) RIDE O ( 49,X'S) H ( 491,X'S) H ( 492,X'S) RIDE O ( 50,X'S) H ( 501,X'S) H ( 502,X'S) RIDE N ( 53,X'S) H ( 531,X'S) RIDE N ( 55,X'S) H ( 551,X'S) H ( 552,X'S) RIDE C ( 56,X'S) H ( 561,X'S) RIDE C ( 57,X'S) H ( 571,X'S) RIDE N ( 58,X'S) H ( 581,X'S) RIDE N ( 61,X'S) H ( 611,X'S) RIDE C ( 62,X'S) H ( 621,X'S) RIDE C ( 63,X'S) H ( 631,X'S) RIDE N ( 65,X'S) H ( 651,X'S) RIDE N ( 66,X'S) H ( 662,X'S) H ( 661,X'S) RIDE N ( 69,X'S) H ( 691,X'S) RIDE N ( 71,X'S) H ( 711,X'S) H ( 712,X'S) RIDE C ( 72,X'S) H ( 721,X'S) RIDE C ( 73,X'S) H ( 731,X'S) RIDE N ( 74,X'S) H ( 741,X'S) RIDE O ( 75,X'S) H ( 751,X'S) H ( 752,X'S) RIDE O ( 76,X'S) H ( 761,X'S) H ( 762,X'S) RIDE O ( 77,X'S) H ( 771,X'S) H ( 772,X'S) RIDE O ( 78,X'S) H ( 781,X'S) H ( 782,X'S) RIDE O ( 79,X'S) H ( 791,X'S) H ( 792,X'S) RIDE O ( 80,X'S) H ( 801,X'S) H ( 802,X'S) RIDE N ( 84,X'S) H ( 841,X'S) RIDE N ( 85,X'S) H ( 851,X'S) RIDE N ( 88,X'S) H ( 882,X'S) H ( 881,X'S) RIDE C ( 89,X'S) H ( 891,X'S) RIDE C ( 90,X'S) H ( 901,X'S) RIDE C ( 91,X'S) H ( 911,X'S) RIDE C ( 92,X'S) H ( 921,X'S) RIDE N ( 93,X'S) H ( 931,X'S) RIDE N ( 94,X'S) H ( 941,X'S) RIDE N ( 95,X'S) H ( 951,X'S) H ( 952,X'S) RIDE O ( 96,X'S) H ( 961,X'S) H ( 962,X'S) RIDE O ( 97,X'S) H ( 971,X'S) REM TOO MANY H ATOMS ON C ( 98), - 6 RIDE C ( 98,X'S) H ( 986,X'S) H ( 985,X'S) H ( 984,X'S) END ;

_iucr_refine_instruction_details_restraints ; # # Punched on 30/03/12 at 11:44:50 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) U(IJ)'S 0.0, 0.0050000 = N(84) TO N(85) U(IJ)'S 0.0, 0.0050000 = O(81) TO O(82) U(IJ)'S 0.0, 0.0010000 = N(93) TO N(94) U(IJ)'S 0.0, 0.0050000 = C(90) TO C(92) U(IJ)'S 0.0, 0.0050000 = C(89) TO C(91) U(IJ)'S 0.0, 0.0050000 = C(86) TO C(87) U(IJ)'S 0.0, 0.0050000 = N(88) TO N(95) END ;

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