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Stability Determination for Cyclized 2,4-Dinitophenyl Hydrazone Derivative of Glucose

Stability Determination for Cyclized 2,4-Dinitophenyl Hydrazone Derivative of Glucose

<p> Supporting Information</p><p>Stability determination for cyclized 2,4-dinitophenyl hydrazone derivative of glucose Muhammed Alzweiria,b, Sara Al-Marabeha,d, Sanaa K. Bardaweela, Rawhi Alfarc</p><p> and Yusuf M. Al-Hiaria</p><p> aDepartment of Pharmaceutical Sciences, Faculty of Pharmacy, The University of Jordan, Amman-11942, Jordan.</p><p> bFaculty of Pharmacy, Al-Zaytoonah Private University of Jordan, Amman 11733, Jordan</p><p> cDepartment of Physics, School of Science, Al-Balqa Applied University, Salt, Jordan.</p><p> dFaculty of Pharmacy, Zarqa University, Zarqa 13132, Jordan.</p><p>*Corresponding author; E-Mail: [email protected]</p><p>Lecturer at Zarqa University Pharmaceutical Sciences Department Faculty of Pharmacy Zarqa University Zarqa 13132 Jordan</p><p>Table 1: Crystal data and structure refinement</p><p>S1 Table 2: Atomic coordinates and equivalent isotropic displacement parameters</p><p>Table 3: Bond lengths [Å[ and angles [°]</p><p>Table 4: Anisotropic displacement parameters</p><p>Table 5: Hydrogen coordinates and isotropic displacement parameters</p><p>Table 6: Torsion angles [°]</p><p>Table 7: Hydrogen bonds [Å and °].</p><p>Table 1: Crystal data and structure refinement</p><p>Identification code CCDC # 960088</p><p>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°.</p><p>Volume 875.7(2) Å 3 Z 2</p><p>Density (calculated) 1.541 Mg/m3</p><p>Absorption coefficient 1.143 mm-1 F (000) 428</p><p>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</p><p>Refinement method Full-matrix least-squares on F2 Data / restraints / parameters 2742 / 1 / 296</p><p>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)</p><p>S3 Extinction coefficient 0.0021(16)</p><p>Largest diff. peak and hole 0.465 and -0.450 e. Å-3</p><p>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. ______</p><p> x y z U(eq)</p><p>______</p><p>O(1) 7767(3) 6181(7) 7029(3) 23(1)</p><p>N(1) 9746(3) 6229(10) 7019(3) 25(1)</p><p>C(1') 11124(4) 5492(10) 8615(4) 23(1)</p><p>O(2) 9193(3) 10994(7) 5968(3) 27(1)</p><p>N(2) 10098(4) 4878(9) 7888(3) 25(1)</p><p>C(2') 11531(4) 4162(11) 9507(4) 24(1)</p><p>C(2) 8719(4) 7776(10) 6960(4) 22(1)</p><p>O(3) 6754(3) 11451(9) 4871(3) 28(1)</p><p>N(3) 10904(4) 2106(9) 9739(3) 26(1)</p><p>C(3') 12634(4) 4772(11) 10223(4) 23(1)</p><p>C(3) 8338(4) 9159(10) 6001(4) 22(1)</p><p>C(4) 7145(4) 10465(10) 5845(4) 23(1)</p><p>N(4) 14429(4) 7257(10) 10798(3) 27(1)</p><p>O(4) 5091(3) 9785(8) 5858(3) 26(1)</p><p>C(4') 13264(4) 6682(12) 10045(4) 25(1)</p><p>C(5) 6234(4) 8664(10) 6003(4) 21(1)</p><p>C(5') 12897(4) 8072(11) 9187(4) 27(1)</p><p>S4 O(5) 5240(3) 4261(8) 6541(3) 29(1)</p><p>C(6) 6728(4) 7565(11) 7032(4) 24(1)</p><p>C(6') 11823(4) 7423(11) 8479(4) 26(1)</p><p>O(6) 11295(3) 1128(8) 10546(3) 34(1)</p><p>C(7) 5866(5) 5862(12) 7309(4) 26(1)</p><p>O(7) 9972(3) 1372(8) 9106(3) 31(1)</p><p>C(8) 7784(5) 7646(12) 3144(4) 33(1)</p><p>O(8) 14786(3) 5915(10) 11508(3) 37(1)</p><p>C(9) 7568(4) 5458(11) 3671(4) 28(1)</p><p>O(9) 14965(4) 9044(10) 10660(3) 43(1)</p><p>O(10) 8702(3) 4637(8) 4369(3) 30(1)</p><p>Table 3: Bond lengths [Å[ and angles [°]</p><p>______</p><p>O(1)-C(6) 1.440(6)</p><p>O(1)-C(2) 1.448(6)</p><p>N(1)-N(2) 1.394(7)</p><p>N(1)-C(2) 1.456(6)</p><p>N(1)-H(1A) 0.8800</p><p>C(1')-N(2) 1.364(7)</p><p>C(1')-C(6') 1.389(8)</p><p>C(1')-C(2') 1.417(8)</p><p>O(2)-C(3) 1.432(6)</p><p>S5 O(2)-H(2) 0.8400</p><p>N(2)-H(2A) 0.99(7)</p><p>C(2')-C(3') 1.417(7)</p><p>C(2')-N(3) 1.440(7)</p><p>C(2)-C(3) 1.509(8)</p><p>C(2)-H(2") 1.0000</p><p>O(3)-C(4) 1.430(7)</p><p>O(3)-H(3) 0.81(7)</p><p>N(3)-O(6) 1.225(6)</p><p>N(3)-O(7) 1.248(6)</p><p>C(3')-C(4') 1.351(8)</p><p>C(3')-H(3') 1.08(6)</p><p>C(3)-C(4) 1.527(6)</p><p>C(3)-H(3") 0.83(6)</p><p>C(4)-C(5) 1.525(7)</p><p>C(4)-H(4") 1.0000</p><p>N(4)-O(9) 1.213(7)</p><p>N(4)-O(8) 1.217(7)</p><p>N(4)-C(4') 1.485(6)</p><p>O(4)-C(5) 1.433(6)</p><p>O(4)-H(4) 0.91(8)</p><p>C(4')-C(5') 1.394(8)</p><p>C(5)-C(6) 1.528(7)</p><p>C(5)-H(5") 1.06(5)</p><p>S6 C(5')-C(6') 1.394(8)</p><p>C(5')-H(5') 1.00(6)</p><p>O(5)-C(7) 1.417(7)</p><p>O(5)-H(5) 0.8400</p><p>C(6)-C(7) 1.521(8)</p><p>C(6)-H(6") 1.0000</p><p>C(6')-H(6') 0.91(5)</p><p>C(7)-H(7B) 0.93(7)</p><p>C(7)-H(7A) 0.95(7)</p><p>C(8)-C(9) 1.480(9)</p><p>C(8)-H(8A) 0.9800</p><p>C(8)-H(8B) 0.9800</p><p>C(8)-H(8C) 0.9800</p><p>C(9)-O(10) 1.462(7)</p><p>C(9)-H(9A) 0.9900</p><p>C(9)-H(9B) 0.9900</p><p>O(10)-H(10) 0.8400</p><p>C(6)-O(1)-C(2) 111.2(4)</p><p>N(2)-N(1)-C(2) 111.3(4)</p><p>N(2)-N(1)-H(1A) 124.3</p><p>C(2)-N(1)-H(1A) 124.3</p><p>N(2)-C(1')-C(6') 120.0(5)</p><p>N(2)-C(1')-C(2') 121.9(5)</p><p>S7 C(6')-C(1')-C(2') 118.1(5)</p><p>C(3)-O(2)-H(2) 109.5</p><p>C(1')-N(2)-N(1) 119.5(5)</p><p>C(1')-N(2)-H(2A) 111(4)</p><p>N(1)-N(2)-H(2A) 129(4)</p><p>C(3')-C(2')-C(1') 120.3(5)</p><p>C(3')-C(2')-N(3) 115.8(5)</p><p>C(1')-C(2')-N(3) 123.9(5)</p><p>O(1)-C(2)-N(1) 107.1(4)</p><p>O(1)-C(2)-C(3) 110.6(4)</p><p>N(1)-C(2)-C(3) 110.1(4)</p><p>O(1)-C(2)-H(2") 109.7</p><p>N(1)-C(2)-H(2") 109.7</p><p>C(3)-C(2)-H(2") 109.7</p><p>C(4)-O(3)-H(3) 109(4)</p><p>O(6)-N(3)-O(7) 121.9(5)</p><p>O(6)-N(3)-C(2') 119.5(5)</p><p>O(7)-N(3)-C(2') 118.7(5)</p><p>C(4')-C(3')-C(2') 118.4(5)</p><p>C(4')-C(3')-H(3') 127(3)</p><p>C(2')-C(3')-H(3') 114(3)</p><p>O(2)-C(3)-C(2) 111.8(4)</p><p>O(2)-C(3)-C(4) 107.0(4)</p><p>C(2)-C(3)-C(4) 111.1(4)</p><p>S8 O(2)-C(3)-H(3") 104(4)</p><p>C(2)-C(3)-H(3") 110(4)</p><p>C(4)-C(3)-H(3") 112(4)</p><p>O(3)-C(4)-C(5) 111.4(4)</p><p>O(3)-C(4)-C(3) 108.3(4)</p><p>C(5)-C(4)-C(3) 109.6(4)</p><p>O(3)-C(4)-H(4") 109.2</p><p>C(5)-C(4)-H(4") 109.2</p><p>C(3)-C(4)-H(4") 109.2</p><p>O(9)-N(4)-O(8) 124.2(5)</p><p>O(9)-N(4)-C(4') 117.4(5)</p><p>O(8)-N(4)-C(4') 118.4(5)</p><p>C(5)-O(4)-H(4) 116(3)</p><p>C(3')-C(4')-C(5') 123.6(5)</p><p>C(3')-C(4')-N(4) 117.5(5)</p><p>C(5')-C(4')-N(4) 118.9(5)</p><p>O(4)-C(5)-C(4) 112.1(4)</p><p>O(4)-C(5)-C(6) 111.1(4)</p><p>C(4)-C(5)-C(6) 109.1(4)</p><p>O(4)-C(5)-H(5") 112(3)</p><p>C(4)-C(5)-H(5") 102(3)</p><p>C(6)-C(5)-H(5") 110(3)</p><p>C(6')-C(5')-C(4') 117.4(5)</p><p>C(6')-C(5')-H(5') 117(3)</p><p>S9 C(4')-C(5')-H(5') 126(3)</p><p>C(7)-O(5)-H(5) 109.5</p><p>O(1)-C(6)-C(7) 108.6(5)</p><p>O(1)-C(6)-C(5) 105.5(4)</p><p>C(7)-C(6)-C(5) 114.4(4)</p><p>O(1)-C(6)-H(6") 109.4</p><p>C(7)-C(6)-H(6") 109.4</p><p>C(5)-C(6)-H(6") 109.4</p><p>C(1')-C(6')-C(5') 122.2(5)</p><p>C(1')-C(6')-H(6') 119(3)</p><p>C(5')-C(6')-H(6') 119(3)</p><p>O(5)-C(7)-C(6) 113.5(4)</p><p>O(5)-C(7)-H(7B) 117(4)</p><p>C(6)-C(7)-H(7B) 104(4)</p><p>O(5)-C(7)-H(7A) 106(4)</p><p>C(6)-C(7)-H(7A) 110(3)</p><p>H(7B)-C(7)-H(7A) 106(5)</p><p>C(9)-C(8)-H(8A) 109.5</p><p>C(9)-C(8)-H(8B) 109.5</p><p>H(8A)-C(8)-H(8B) 109.5</p><p>C(9)-C(8)-H(8C) 109.5</p><p>H(8A)-C(8)-H(8C) 109.5</p><p>H(8B)-C(8)-H(8C) 109.5</p><p>O(10)-C(9)-C(8) 109.3(4)</p><p>S10 O(10)-C(9)-H(9A) 109.8</p><p>C(8)-C(9)-H(9A) 109.8</p><p>O(10)-C(9)-H(9B) 109.8</p><p>C(8)-C(9)-H(9B) 109.8</p><p>H(9A)-C(9)-H(9B) 108.3</p><p>C(9)-O(10)-H(10) 109.5</p><p>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 ] ______</p><p>U11 U22 U33 U23 U13 U12</p><p>______</p><p>O(1) 11(2) 20(2) 36(2) -2(2) 3(1) -1(1)</p><p>N(1) 14(2) 33(3) 27(2) 3(2) 4(2) 8(2)</p><p>C(1') 15(2) 23(3) 31(3) -5(2) 6(2) 3(2)</p><p>O(2) 14(2) 26(2) 40(2) 5(2) 8(1) 1(2)</p><p>N(2) 13(2) 27(3) 30(2) -1(2) 0(2) 2(2)</p><p>C(2') 14(2) 27(3) 28(3) -3(2) 5(2) 2(2)</p><p>C(2) 12(2) 21(3) 32(3) -5(2) 5(2) -1(2)</p><p>O(3) 13(2) 29(2) 38(2) 5(2) 4(1) 3(2)</p><p>N(3) 22(2) 24(3) 32(2) -1(2) 9(2) -2(2)</p><p>C(3') 20(2) 20(3) 27(2) 0(2) 4(2) 4(2)</p><p>C(3) 14(2) 17(3) 32(3) -5(2) 5(2) 0(2)</p><p>C(4) 13(2) 20(3) 32(2) -2(2) 3(2) 0(2)</p><p>S11 N(4) 14(2) 34(3) 31(2) -4(2) 5(2) -2(2)</p><p>O(4) 10(2) 20(2) 43(2) -4(2) 3(1) 4(2)</p><p>C(4') 12(2) 31(3) 27(2) -5(2) -2(2) 1(2)</p><p>C(5) 10(2) 15(3) 36(3) 1(2) 5(2) 3(2)</p><p>C(5') 12(2) 28(3) 40(3) -5(3) 6(2) -2(2)</p><p>O(5) 17(2) 27(2) 39(2) 0(2) 2(2) -1(2)</p><p>C(6) 18(2) 24(3) 29(3) -5(2) 6(2) 0(2)</p><p>C(6') 19(2) 28(3) 29(3) 4(3) 4(2) -1(2)</p><p>O(6) 29(2) 33(3) 37(2) 10(2) 7(2) 0(2)</p><p>C(7) 19(2) 28(3) 31(3) -1(3) 7(2) 3(2)</p><p>O(7) 19(2) 32(2) 36(2) -3(2) 2(2) -2(2)</p><p>C(8) 21(2) 36(4) 40(3) 0(3) 9(2) 2(2)</p><p>O(8) 22(2) 48(3) 33(2) -1(2) -2(2) 1(2)</p><p>C(9) 18(2) 26(3) 37(3) -5(2) 6(2) -5(2)</p><p>O(9) 24(2) 54(3) 45(2) -4(2) 5(2) -20(2)</p><p>O(10) 15(2) 30(2) 44(2) 4(2) 9(2) 0(2)</p><p>______</p><p>Table 5: Hydrogen coordinates ( x 104) and isotropic displacement parameters (Å2 x 10 3) ______x y z U(eq) ______</p><p>S12 H(1A) 10099 6155 6564 30</p><p>H(2) 9605 10490 5625 40</p><p>H(2A) 9640(60) 3590(130) 8110(40) 23(14)</p><p>H(2") 8933 8960 7521 27</p><p>H(3) 6390(50) 12710(130) 4870(40) 13(14)</p><p>H(3') 12900(50) 3520(120) 10840(40) 13(12)</p><p>H(3") 8320(50) 8210(120) 5540(40) 16(14)</p><p>H(4") 7264 11833 6330 27</p><p>H(4) 5110(50) 11350(140) 6080(40) 14(13)</p><p>H(5") 6190(40) 7300(100) 5460(30) 4(11)</p><p>H(5') 13350(50) 9470(120) 9020(40) 12(12)</p><p>H(5) 4728 5058 6104 44</p><p>H(6") 6975 8913 7526 29</p><p>H(6') 11570(40) 8280(100) 7910(40) 3(11)</p><p>H(7B) 5400(60) 6900(140) 7560(40) 27(16)</p><p>H(7A) 6300(50) 4840(130) 7840(40) 15(13)</p><p>H(8A) 7024 8207 2679 49</p><p>H(8B) 8340 7229 2785 49</p><p>H(8C) 8129 8950 3617 49</p><p>H(9A) 6996 5861 4026 33</p><p>H(9B) 7217 4134 3196 33</p><p>H(10) 9273 5158 4192 45 ______</p><p>S13 Table 6: Torsion angles [°] ______</p><p>C(6')-C(1')-N(2)-N(1) -1.2(7)</p><p>C(2')-C(1')-N(2)-N(1) -179.2(4)</p><p>C(2)-N(1)-N(2)-C(1') -107.2(5)</p><p>N(2)-C(1')-C(2')-C(3') 176.6(4)</p><p>C(6')-C(1')-C(2')-C(3') -1.4(7)</p><p>N(2)-C(1')-C(2')-N(3) -1.3(7)</p><p>C(6')-C(1')-C(2')-N(3) -179.3(5)</p><p>C(6)-O(1)-C(2)-N(1) 176.9(4)</p><p>C(6)-O(1)-C(2)-C(3) -63.2(5)</p><p>N(2)-N(1)-C(2)-O(1) -58.1(5)</p><p>N(2)-N(1)-C(2)-C(3) -178.4(4)</p><p>C(3')-C(2')-N(3)-O(6) 5.1(7)</p><p>C(1')-C(2')-N(3)-O(6) -176.9(5)</p><p>C(3')-C(2')-N(3)-O(7) -174.8(4)</p><p>C(1')-C(2')-N(3)-O(7) 3.1(7)</p><p>C(1')-C(2')-C(3')-C(4') 1.8(7)</p><p>N(3)-C(2')-C(3')-C(4') 179.8(5)</p><p>O(1)-C(2)-C(3)-O(2) 171.9(4)</p><p>N(1)-C(2)-C(3)-O(2) -69.9(5)</p><p>O(1)-C(2)-C(3)-C(4) 52.5(6)</p><p>N(1)-C(2)-C(3)-C(4) 170.6(4)</p><p>O(2)-C(3)-C(4)-O(3) 65.5(5)</p><p>C(2)-C(3)-C(4)-O(3) -172.1(4)</p><p>S14 O(2)-C(3)-C(4)-C(5) -172.8(4)</p><p>C(2)-C(3)-C(4)-C(5) -50.5(6)</p><p>C(2')-C(3')-C(4')-C(5') -0.9(8)</p><p>C(2')-C(3')-C(4')-N(4) -178.9(4)</p><p>O(9)-N(4)-C(4')-C(3') -176.4(5)</p><p>O(8)-N(4)-C(4')-C(3') 3.8(7)</p><p>O(9)-N(4)-C(4')-C(5') 5.5(7)</p><p>O(8)-N(4)-C(4')-C(5') -174.3(5)</p><p>O(3)-C(4)-C(5)-O(4) -59.7(6)</p><p>C(3)-C(4)-C(5)-O(4) -179.5(4)</p><p>O(3)-C(4)-C(5)-C(6) 176.9(4)</p><p>C(3)-C(4)-C(5)-C(6) 57.0(5)</p><p>C(3')-C(4')-C(5')-C(6') -0.4(8)</p><p>N(4)-C(4')-C(5')-C(6') 177.6(5)</p><p>C(2)-O(1)-C(6)-C(7) -168.8(4)</p><p>C(2)-O(1)-C(6)-C(5) 68.2(5)</p><p>O(4)-C(5)-C(6)-O(1) 171.2(4)</p><p>C(4)-C(5)-C(6)-O(1) -64.8(5)</p><p>O(4)-C(5)-C(6)-C(7) 51.9(6)</p><p>C(4)-C(5)-C(6)-C(7) 176.0(4)</p><p>N(2)-C(1')-C(6')-C(5') -177.9(5)</p><p>C(2')-C(1')-C(6')-C(5') 0.1(8)</p><p>C(4')-C(5')-C(6')-C(1') 0.8(8)</p><p>O(1)-C(6)-C(7)-O(5) -75.3(6)</p><p>S15 C(5)-C(6)-C(7)-O(5) 42.2(6)</p><p>______</p><p>Table 7: Hydrogen bonds [Å and °]. ______</p><p>D-H...A d(D-H) d(H...A) d(D...A) <(DHA)</p><p>______</p><p>O(2)-H(2)...O(10)#1 0.84 2.05 2.774(5) 144.8</p><p>N(2)-H(2A)...O(7) 0.99(7) 1.82(7) 2.629(7) 136(5)</p><p>O(3)-H(3)...O(4)#2 0.81(7) 2.06(7) 2.773(6) 146(6)</p><p>O(4)-H(4)...O(5)#3 0.91(8) 1.71(8) 2.619(6) 176(5)</p><p>O(5)-H(5)...O(3)#4 0.84 2.01 2.834(6) 167.2</p><p>O(10)-H(10)...O(2)#5 0.84 1.95 2.774(5) 167.7</p><p>______</p><p>Symmetry transformations used to generate equivalent atoms: </p><p>#1 -x+2,y+1/2,-z+1 #2 -x+1,y+1/2,-z+1 #3 x,y+1,z </p><p>#4 -x+1,y-1/2,-z+1 #5 -x+2,y-1/2,-z+1 </p><p>S16</p>

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