Supporting Information

Stability determination for cyclized 2,4-dinitophenyl hydrazone derivative of glucose Muhammed Alzweiria,b, Sara Al-Marabeha,d, Sanaa K. Bardaweela, Rawhi Alfarc

and Yusuf M. Al-Hiaria

aDepartment of Pharmaceutical Sciences, Faculty of Pharmacy, The University of Jordan, Amman-11942, Jordan.

bFaculty of Pharmacy, Al-Zaytoonah Private University of Jordan, Amman 11733, Jordan

cDepartment of Physics, School of Science, Al-Balqa Applied University, Salt, Jordan.

dFaculty of Pharmacy, Zarqa University, Zarqa 13132, Jordan.

*Corresponding author; E-Mail: [email protected]

Lecturer at Zarqa University Pharmaceutical Sciences Department Faculty of Pharmacy Zarqa University Zarqa 13132 Jordan

Table 1: Crystal data and structure refinement

S1 Table 2: Atomic coordinates and equivalent isotropic displacement parameters

Table 3: Bond lengths [Å[ and angles [°]

Table 4: Anisotropic displacement parameters

Table 5: Hydrogen coordinates and isotropic displacement parameters

Table 6: Torsion angles [°]

Table 7: Hydrogen bonds [Å and °].

Table 1: Crystal data and structure refinement

Identification code CCDC # 960088

S2 Empirical formula C14 H22 N4 O10 Formula weight 406.36 Temperature 293(2) K Wavelength 1.54184 Å Crystal system Monoclinic Space group P 21 Unit cell dimensions a = 11.7794(13) Å = 90°. b = 5.4626(7) Å = 108.539(14) °. c = 14.354(2) Å  = 90°.

Volume 875.7(2) Å 3 Z 2

Density (calculated) 1.541 Mg/m3

Absorption coefficient 1.143 mm-1 F (000) 428

Crystal size 0.4627 x 0.0408 x 0.018 mm3 Theta range for data collection 3.25 to 66.58°. Index ranges -14<=h<=13, -6<=k<=5, -17<=l<=11 Reflections collected 2742 Independent reflections 2742 [R (int) = 0.0564] Completeness to theta = 66.58° 98.2 % Absorption correction Semi-empirical from equivalents Max. and min. transmission 0.980 and 0.946

Refinement method Full-matrix least-squares on F2 Data / restraints / parameters 2742 / 1 / 296

Goodness-of-fit on F2 1.061 Final R indices [I>2\s(I)] R1 = 0.0703, wR2 = 0.1737 R indices (all data) R1 = 0.0781, wR2 = 0.1826 Absolute structure parameter 0.1(5)

S3 Extinction coefficient 0.0021(16)

Largest diff. peak and hole 0.465 and -0.450 e. Å-3

Table 2: Atomic coordinates (x 104) and equivalent isotropic displacement parameters (Å2 x 103) U(eq) is defined as one third of the trace of the orthogonalized Uij tensor. ______

x y z U(eq)

______

O(1) 7767(3) 6181(7) 7029(3) 23(1)

N(1) 9746(3) 6229(10) 7019(3) 25(1)

C(1') 11124(4) 5492(10) 8615(4) 23(1)

O(2) 9193(3) 10994(7) 5968(3) 27(1)

N(2) 10098(4) 4878(9) 7888(3) 25(1)

C(2') 11531(4) 4162(11) 9507(4) 24(1)

C(2) 8719(4) 7776(10) 6960(4) 22(1)

O(3) 6754(3) 11451(9) 4871(3) 28(1)

N(3) 10904(4) 2106(9) 9739(3) 26(1)

C(3') 12634(4) 4772(11) 10223(4) 23(1)

C(3) 8338(4) 9159(10) 6001(4) 22(1)

C(4) 7145(4) 10465(10) 5845(4) 23(1)

N(4) 14429(4) 7257(10) 10798(3) 27(1)

O(4) 5091(3) 9785(8) 5858(3) 26(1)

C(4') 13264(4) 6682(12) 10045(4) 25(1)

C(5) 6234(4) 8664(10) 6003(4) 21(1)

C(5') 12897(4) 8072(11) 9187(4) 27(1)

S4 O(5) 5240(3) 4261(8) 6541(3) 29(1)

C(6) 6728(4) 7565(11) 7032(4) 24(1)

C(6') 11823(4) 7423(11) 8479(4) 26(1)

O(6) 11295(3) 1128(8) 10546(3) 34(1)

C(7) 5866(5) 5862(12) 7309(4) 26(1)

O(7) 9972(3) 1372(8) 9106(3) 31(1)

C(8) 7784(5) 7646(12) 3144(4) 33(1)

O(8) 14786(3) 5915(10) 11508(3) 37(1)

C(9) 7568(4) 5458(11) 3671(4) 28(1)

O(9) 14965(4) 9044(10) 10660(3) 43(1)

O(10) 8702(3) 4637(8) 4369(3) 30(1)

Table 3: Bond lengths [Å[ and angles [°]

______

O(1)-C(6) 1.440(6)

O(1)-C(2) 1.448(6)

N(1)-N(2) 1.394(7)

N(1)-C(2) 1.456(6)

N(1)-H(1A) 0.8800

C(1')-N(2) 1.364(7)

C(1')-C(6') 1.389(8)

C(1')-C(2') 1.417(8)

O(2)-C(3) 1.432(6)

S5 O(2)-H(2) 0.8400

N(2)-H(2A) 0.99(7)

C(2')-C(3') 1.417(7)

C(2')-N(3) 1.440(7)

C(2)-C(3) 1.509(8)

C(2)-H(2") 1.0000

O(3)-C(4) 1.430(7)

O(3)-H(3) 0.81(7)

N(3)-O(6) 1.225(6)

N(3)-O(7) 1.248(6)

C(3')-C(4') 1.351(8)

C(3')-H(3') 1.08(6)

C(3)-C(4) 1.527(6)

C(3)-H(3") 0.83(6)

C(4)-C(5) 1.525(7)

C(4)-H(4") 1.0000

N(4)-O(9) 1.213(7)

N(4)-O(8) 1.217(7)

N(4)-C(4') 1.485(6)

O(4)-C(5) 1.433(6)

O(4)-H(4) 0.91(8)

C(4')-C(5') 1.394(8)

C(5)-C(6) 1.528(7)

C(5)-H(5") 1.06(5)

S6 C(5')-C(6') 1.394(8)

C(5')-H(5') 1.00(6)

O(5)-C(7) 1.417(7)

O(5)-H(5) 0.8400

C(6)-C(7) 1.521(8)

C(6)-H(6") 1.0000

C(6')-H(6') 0.91(5)

C(7)-H(7B) 0.93(7)

C(7)-H(7A) 0.95(7)

C(8)-C(9) 1.480(9)

C(8)-H(8A) 0.9800

C(8)-H(8B) 0.9800

C(8)-H(8C) 0.9800

C(9)-O(10) 1.462(7)

C(9)-H(9A) 0.9900

C(9)-H(9B) 0.9900

O(10)-H(10) 0.8400

C(6)-O(1)-C(2) 111.2(4)

N(2)-N(1)-C(2) 111.3(4)

N(2)-N(1)-H(1A) 124.3

C(2)-N(1)-H(1A) 124.3

N(2)-C(1')-C(6') 120.0(5)

N(2)-C(1')-C(2') 121.9(5)

S7 C(6')-C(1')-C(2') 118.1(5)

C(3)-O(2)-H(2) 109.5

C(1')-N(2)-N(1) 119.5(5)

C(1')-N(2)-H(2A) 111(4)

N(1)-N(2)-H(2A) 129(4)

C(3')-C(2')-C(1') 120.3(5)

C(3')-C(2')-N(3) 115.8(5)

C(1')-C(2')-N(3) 123.9(5)

O(1)-C(2)-N(1) 107.1(4)

O(1)-C(2)-C(3) 110.6(4)

N(1)-C(2)-C(3) 110.1(4)

O(1)-C(2)-H(2") 109.7

N(1)-C(2)-H(2") 109.7

C(3)-C(2)-H(2") 109.7

C(4)-O(3)-H(3) 109(4)

O(6)-N(3)-O(7) 121.9(5)

O(6)-N(3)-C(2') 119.5(5)

O(7)-N(3)-C(2') 118.7(5)

C(4')-C(3')-C(2') 118.4(5)

C(4')-C(3')-H(3') 127(3)

C(2')-C(3')-H(3') 114(3)

O(2)-C(3)-C(2) 111.8(4)

O(2)-C(3)-C(4) 107.0(4)

C(2)-C(3)-C(4) 111.1(4)

S8 O(2)-C(3)-H(3") 104(4)

C(2)-C(3)-H(3") 110(4)

C(4)-C(3)-H(3") 112(4)

O(3)-C(4)-C(5) 111.4(4)

O(3)-C(4)-C(3) 108.3(4)

C(5)-C(4)-C(3) 109.6(4)

O(3)-C(4)-H(4") 109.2

C(5)-C(4)-H(4") 109.2

C(3)-C(4)-H(4") 109.2

O(9)-N(4)-O(8) 124.2(5)

O(9)-N(4)-C(4') 117.4(5)

O(8)-N(4)-C(4') 118.4(5)

C(5)-O(4)-H(4) 116(3)

C(3')-C(4')-C(5') 123.6(5)

C(3')-C(4')-N(4) 117.5(5)

C(5')-C(4')-N(4) 118.9(5)

O(4)-C(5)-C(4) 112.1(4)

O(4)-C(5)-C(6) 111.1(4)

C(4)-C(5)-C(6) 109.1(4)

O(4)-C(5)-H(5") 112(3)

C(4)-C(5)-H(5") 102(3)

C(6)-C(5)-H(5") 110(3)

C(6')-C(5')-C(4') 117.4(5)

C(6')-C(5')-H(5') 117(3)

S9 C(4')-C(5')-H(5') 126(3)

C(7)-O(5)-H(5) 109.5

O(1)-C(6)-C(7) 108.6(5)

O(1)-C(6)-C(5) 105.5(4)

C(7)-C(6)-C(5) 114.4(4)

O(1)-C(6)-H(6") 109.4

C(7)-C(6)-H(6") 109.4

C(5)-C(6)-H(6") 109.4

C(1')-C(6')-C(5') 122.2(5)

C(1')-C(6')-H(6') 119(3)

C(5')-C(6')-H(6') 119(3)

O(5)-C(7)-C(6) 113.5(4)

O(5)-C(7)-H(7B) 117(4)

C(6)-C(7)-H(7B) 104(4)

O(5)-C(7)-H(7A) 106(4)

C(6)-C(7)-H(7A) 110(3)

H(7B)-C(7)-H(7A) 106(5)

C(9)-C(8)-H(8A) 109.5

C(9)-C(8)-H(8B) 109.5

H(8A)-C(8)-H(8B) 109.5

C(9)-C(8)-H(8C) 109.5

H(8A)-C(8)-H(8C) 109.5

H(8B)-C(8)-H(8C) 109.5

O(10)-C(9)-C(8) 109.3(4)

S10 O(10)-C(9)-H(9A) 109.8

C(8)-C(9)-H(9A) 109.8

O(10)-C(9)-H(9B) 109.8

C(8)-C(9)-H(9B) 109.8

H(9A)-C(9)-H(9B) 108.3

C(9)-O(10)-H(10) 109.5

Table 4: Anisotropic displacement parameters (Å2 x 103) The anisotropic displacement factor exponent takes the form: -22[ h2 a*2U11 + ... + 2 h k a* b* U12 ] ______

U11 U22 U33 U23 U13 U12

______

O(1) 11(2) 20(2) 36(2) -2(2) 3(1) -1(1)

N(1) 14(2) 33(3) 27(2) 3(2) 4(2) 8(2)

C(1') 15(2) 23(3) 31(3) -5(2) 6(2) 3(2)

O(2) 14(2) 26(2) 40(2) 5(2) 8(1) 1(2)

N(2) 13(2) 27(3) 30(2) -1(2) 0(2) 2(2)

C(2') 14(2) 27(3) 28(3) -3(2) 5(2) 2(2)

C(2) 12(2) 21(3) 32(3) -5(2) 5(2) -1(2)

O(3) 13(2) 29(2) 38(2) 5(2) 4(1) 3(2)

N(3) 22(2) 24(3) 32(2) -1(2) 9(2) -2(2)

C(3') 20(2) 20(3) 27(2) 0(2) 4(2) 4(2)

C(3) 14(2) 17(3) 32(3) -5(2) 5(2) 0(2)

C(4) 13(2) 20(3) 32(2) -2(2) 3(2) 0(2)

S11 N(4) 14(2) 34(3) 31(2) -4(2) 5(2) -2(2)

O(4) 10(2) 20(2) 43(2) -4(2) 3(1) 4(2)

C(4') 12(2) 31(3) 27(2) -5(2) -2(2) 1(2)

C(5) 10(2) 15(3) 36(3) 1(2) 5(2) 3(2)

C(5') 12(2) 28(3) 40(3) -5(3) 6(2) -2(2)

O(5) 17(2) 27(2) 39(2) 0(2) 2(2) -1(2)

C(6) 18(2) 24(3) 29(3) -5(2) 6(2) 0(2)

C(6') 19(2) 28(3) 29(3) 4(3) 4(2) -1(2)

O(6) 29(2) 33(3) 37(2) 10(2) 7(2) 0(2)

C(7) 19(2) 28(3) 31(3) -1(3) 7(2) 3(2)

O(7) 19(2) 32(2) 36(2) -3(2) 2(2) -2(2)

C(8) 21(2) 36(4) 40(3) 0(3) 9(2) 2(2)

O(8) 22(2) 48(3) 33(2) -1(2) -2(2) 1(2)

C(9) 18(2) 26(3) 37(3) -5(2) 6(2) -5(2)

O(9) 24(2) 54(3) 45(2) -4(2) 5(2) -20(2)

O(10) 15(2) 30(2) 44(2) 4(2) 9(2) 0(2)

______

Table 5: Hydrogen coordinates ( x 104) and isotropic displacement parameters (Å2 x 10 3) ______x y z U(eq) ______

S12 H(1A) 10099 6155 6564 30

H(2) 9605 10490 5625 40

H(2A) 9640(60) 3590(130) 8110(40) 23(14)

H(2") 8933 8960 7521 27

H(3) 6390(50) 12710(130) 4870(40) 13(14)

H(3') 12900(50) 3520(120) 10840(40) 13(12)

H(3") 8320(50) 8210(120) 5540(40) 16(14)

H(4") 7264 11833 6330 27

H(4) 5110(50) 11350(140) 6080(40) 14(13)

H(5") 6190(40) 7300(100) 5460(30) 4(11)

H(5') 13350(50) 9470(120) 9020(40) 12(12)

H(5) 4728 5058 6104 44

H(6") 6975 8913 7526 29

H(6') 11570(40) 8280(100) 7910(40) 3(11)

H(7B) 5400(60) 6900(140) 7560(40) 27(16)

H(7A) 6300(50) 4840(130) 7840(40) 15(13)

H(8A) 7024 8207 2679 49

H(8B) 8340 7229 2785 49

H(8C) 8129 8950 3617 49

H(9A) 6996 5861 4026 33

H(9B) 7217 4134 3196 33

H(10) 9273 5158 4192 45 ______

S13 Table 6: Torsion angles [°] ______

C(6')-C(1')-N(2)-N(1) -1.2(7)

C(2')-C(1')-N(2)-N(1) -179.2(4)

C(2)-N(1)-N(2)-C(1') -107.2(5)

N(2)-C(1')-C(2')-C(3') 176.6(4)

C(6')-C(1')-C(2')-C(3') -1.4(7)

N(2)-C(1')-C(2')-N(3) -1.3(7)

C(6')-C(1')-C(2')-N(3) -179.3(5)

C(6)-O(1)-C(2)-N(1) 176.9(4)

C(6)-O(1)-C(2)-C(3) -63.2(5)

N(2)-N(1)-C(2)-O(1) -58.1(5)

N(2)-N(1)-C(2)-C(3) -178.4(4)

C(3')-C(2')-N(3)-O(6) 5.1(7)

C(1')-C(2')-N(3)-O(6) -176.9(5)

C(3')-C(2')-N(3)-O(7) -174.8(4)

C(1')-C(2')-N(3)-O(7) 3.1(7)

C(1')-C(2')-C(3')-C(4') 1.8(7)

N(3)-C(2')-C(3')-C(4') 179.8(5)

O(1)-C(2)-C(3)-O(2) 171.9(4)

N(1)-C(2)-C(3)-O(2) -69.9(5)

O(1)-C(2)-C(3)-C(4) 52.5(6)

N(1)-C(2)-C(3)-C(4) 170.6(4)

O(2)-C(3)-C(4)-O(3) 65.5(5)

C(2)-C(3)-C(4)-O(3) -172.1(4)

S14 O(2)-C(3)-C(4)-C(5) -172.8(4)

C(2)-C(3)-C(4)-C(5) -50.5(6)

C(2')-C(3')-C(4')-C(5') -0.9(8)

C(2')-C(3')-C(4')-N(4) -178.9(4)

O(9)-N(4)-C(4')-C(3') -176.4(5)

O(8)-N(4)-C(4')-C(3') 3.8(7)

O(9)-N(4)-C(4')-C(5') 5.5(7)

O(8)-N(4)-C(4')-C(5') -174.3(5)

O(3)-C(4)-C(5)-O(4) -59.7(6)

C(3)-C(4)-C(5)-O(4) -179.5(4)

O(3)-C(4)-C(5)-C(6) 176.9(4)

C(3)-C(4)-C(5)-C(6) 57.0(5)

C(3')-C(4')-C(5')-C(6') -0.4(8)

N(4)-C(4')-C(5')-C(6') 177.6(5)

C(2)-O(1)-C(6)-C(7) -168.8(4)

C(2)-O(1)-C(6)-C(5) 68.2(5)

O(4)-C(5)-C(6)-O(1) 171.2(4)

C(4)-C(5)-C(6)-O(1) -64.8(5)

O(4)-C(5)-C(6)-C(7) 51.9(6)

C(4)-C(5)-C(6)-C(7) 176.0(4)

N(2)-C(1')-C(6')-C(5') -177.9(5)

C(2')-C(1')-C(6')-C(5') 0.1(8)

C(4')-C(5')-C(6')-C(1') 0.8(8)

O(1)-C(6)-C(7)-O(5) -75.3(6)

S15 C(5)-C(6)-C(7)-O(5) 42.2(6)

______

Table 7: Hydrogen bonds [Å and °]. ______

D-H...A d(D-H) d(H...A) d(D...A) <(DHA)

______

O(2)-H(2)...O(10)#1 0.84 2.05 2.774(5) 144.8

N(2)-H(2A)...O(7) 0.99(7) 1.82(7) 2.629(7) 136(5)

O(3)-H(3)...O(4)#2 0.81(7) 2.06(7) 2.773(6) 146(6)

O(4)-H(4)...O(5)#3 0.91(8) 1.71(8) 2.619(6) 176(5)

O(5)-H(5)...O(3)#4 0.84 2.01 2.834(6) 167.2

O(10)-H(10)...O(2)#5 0.84 1.95 2.774(5) 167.7

______

Symmetry transformations used to generate equivalent atoms:

#1 -x+2,y+1/2,-z+1 #2 -x+1,y+1/2,-z+1 #3 x,y+1,z

#4 -x+1,y-1/2,-z+1 #5 -x+2,y-1/2,-z+1

S16