Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S205252062000373X/xk5066sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S205252062000373X/xk5066furazidin_formIIsup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S205252062000373X/xk5066furazidin_formIsup3.hkl | |
Text file https://doi.org/10.1107/S205252062000373X/xk5066sup4.txt | |
Text file https://doi.org/10.1107/S205252062000373X/xk5066sup5.txt | |
Text file https://doi.org/10.1107/S205252062000373X/xk5066sup6.txt | |
Text file https://doi.org/10.1107/S205252062000373X/xk5066sup7.txt | |
Text file https://doi.org/10.1107/S205252062000373X/xk5066sup8.txt | |
Text file https://doi.org/10.1107/S205252062000373X/xk5066sup9.txt | |
Portable Document Format (PDF) file https://doi.org/10.1107/S205252062000373X/xk5066sup10.pdf |
CCDC references: 1993854; 1993855
For both structures, program(s) used to refine structure: GSAS-II (Toby & Von Dreele, J. Appl. Cryst. 46, 544-549, 2013).
C10H8N4O5 | β = 106.848 (14)° |
Mr = 264.2 | V = 1087.80 (18) Å3 |
Monoclinic, P21/c | Z = 4 |
Hall symbol: -P 2ybc | Dx = 1.613 Mg m−3 |
a = 11.670 (7) Å | Cu Kα radiation |
b = 11.4666 (12) Å | T = 300 K |
c = 8.494 (4) Å |
Least-squares matrix: full | R(F2) = 0.04496 |
Rp = 0.071 | 1921 data points |
Rwp = 0.096 | 32 parameters |
Rexp = 0.316 | Background function: Background function: "chebyschev" function with 24 terms: 6.39(6), -11.28(29), -1.7(8), 1.0(22), 209.4(24), 78(4), -2446.0(10), -1372.6(11), 20455.6(21), 11208(3), -117679.9(15), -34269(4), 414751.5(7), 26568.1(15), -893273.9(17), 87213.0(23), 1.1848209(23)e6, -251999(5), -945917.0(18), 281839(4), 417242.8(5), -151823.0(10), -78161(3), 32564(7), |
x | y | z | Uiso*/Ueq | ||
H1 | 0.82787 | −0.06253 | 1.00513 | 0.010* | |
H5 | 0.84740 | 0.19903 | 1.07817 | 0.010* | |
H9 | 0.68180 | 0.04856 | 0.80219 | 0.010* | |
H13 | 0.39344 | 0.37273 | 0.39885 | 0.010* | |
H17 | 0.59001 | 0.09301 | 0.52272 | 0.010* | |
H21 | 0.49048 | 0.07430 | 0.64569 | 0.010* | |
H25 | 0.99900 | −0.18311 | 1.23761 | 0.010* | |
H29 | 1.18276 | −0.11085 | 1.50229 | 0.010* | |
C1 | 1.10762 | 0.05823 | 1.41747 | 0.010* | |
C5 | 0.96242 | 0.00211 | 1.20938 | 0.010* | |
C9 | 1.02283 | −0.09617 | 1.28110 | 0.010* | |
C13 | 0.86302 | 0.01664 | 1.06979 | 0.010* | |
C17 | 0.81292 | 0.11971 | 1.01347 | 0.010* | |
C21 | 0.71606 | 0.12834 | 0.86814 | 0.010* | |
C25 | 0.53259 | 0.33898 | 0.61528 | 0.010* | |
C29 | 0.43200 | 0.19445 | 0.44159 | 0.010* | |
C33 | 0.52767 | 0.13693 | 0.57693 | 0.010* | |
C37 | 1.11655 | −0.05989 | 1.41512 | 0.010* | |
N1 | 0.67265 | 0.22973 | 0.81809 | 0.010* | |
N5 | 0.58263 | 0.23383 | 0.67964 | 0.010* | |
N9 | 0.44356 | 0.31104 | 0.47203 | 0.010* | |
N13 | 1.17586 | 0.13997 | 1.52647 | 0.010* | |
O1 | 1.01514 | 0.09787 | 1.29468 | 0.010* | |
O5 | 1.26275 | 0.10219 | 1.63454 | 0.010* | |
O9 | 1.14515 | 0.24256 | 1.50909 | 0.010* | |
O13 | 0.56028 | 0.43441 | 0.67232 | 0.010* | |
O17 | 0.36065 | 0.14639 | 0.32818 | 0.010* |
H1—C13 | 1.0786 | C25—O13 | 1.2024 |
H5—C17 | 1.0784 | C29—C33 | 1.5030 |
H9—C21 | 1.0866 | C29—N9 | 1.3609 |
H13—N9 | 1.0091 | C29—O17 | 1.2083 |
H17—C33 | 1.0904 | C33—H17 | 1.0904 |
H21—C33 | 1.0919 | C33—H21 | 1.0919 |
H25—C9 | 1.0715 | C33—C29 | 1.5030 |
H29—C37 | 1.0748 | C33—N5 | 1.4432 |
C1—C37 | 1.3590 | C37—H29 | 1.0748 |
C1—N13 | 1.3937 | C37—C1 | 1.3590 |
C1—O1 | 1.3442 | C37—C9 | 1.394 |
C5—C9 | 1.3745 | N1—C21 | 1.2900 |
C5—C13 | 1.4078 | N1—N5 | 1.3314 |
C5—O1 | 1.3605 | N5—C25 | 1.3814 |
C9—H25 | 1.0715 | N5—C33 | 1.4432 |
C9—C5 | 1.3745 | N5—N1 | 1.3314 |
C9—C37 | 1.394 | N9—H13 | 1.0091 |
C13—H1 | 1.0786 | N9—C25 | 1.3891 |
C13—C5 | 1.4078 | N9—C29 | 1.3609 |
C13—C17 | 1.3435 | N13—C1 | 1.3937 |
C17—H5 | 1.0784 | N13—O5 | 1.2325 |
C17—C13 | 1.3435 | N13—O9 | 1.2261 |
C17—C21 | 1.4150 | O1—C1 | 1.3442 |
C21—H9 | 1.0866 | O1—C5 | 1.3605 |
C21—C17 | 1.4150 | O5—N13 | 1.2325 |
C21—N1 | 1.2900 | O9—N13 | 1.2261 |
C25—N5 | 1.3814 | O13—C25 | 1.2024 |
C25—N9 | 1.3891 | O17—C29 | 1.2083 |
C37—C1—N13 | 130.432 | C33—C29—O17 | 126.661 |
C37—C1—O1 | 111.923 | N9—C29—O17 | 127.372 |
N13—C1—O1 | 117.625 | H17—C33—H21 | 109.84 |
C9—C5—C13 | 131.449 | H17—C33—C29 | 108.566 |
C9—C5—O1 | 109.328 | H21—C33—C29 | 112.046 |
C13—C5—O1 | 119.214 | H17—C33—N5 | 112.139 |
H25—C9—C5 | 124.159 | H21—C33—N5 | 111.035 |
H25—C9—C37 | 128.531 | C29—C33—N5 | 103.056 |
C5—C9—C37 | 107.31 | H29—C37—C1 | 125.073 |
H1—C13—C5 | 115.348 | H29—C37—C9 | 129.608 |
H1—C13—C17 | 119.802 | C1—C37—C9 | 105.312 |
C5—C13—C17 | 124.841 | C21—N1—N5 | 117.189 |
H5—C17—C13 | 120.056 | C25—N5—C33 | 111.713 |
H5—C17—C21 | 118.114 | C25—N5—N1 | 121.01 |
C13—C17—C21 | 121.822 | C33—N5—N1 | 127.253 |
H9—C21—C17 | 118.189 | H13—N9—C25 | 122.056 |
H9—C21—N1 | 122.557 | H13—N9—C29 | 124.317 |
C17—C21—N1 | 119.251 | C25—N9—C29 | 113.627 |
N5—C25—N9 | 105.567 | C1—N13—O5 | 116.533 |
N5—C25—O13 | 126.973 | C1—N13—O9 | 118.324 |
N9—C25—O13 | 127.458 | O5—N13—O9 | 125.141 |
C33—C29—N9 | 105.961 | C1—O1—C5 | 106.127 |
C20H16N8O10 | β = 92.16 (3)° |
Mr = 528.39 | γ = 97.31 (11)° |
Triclinic, P1 | V = 1138.5 (4) Å3 |
Hall symbol: -P 1 | Z = 2 |
a = 22.18 (2) Å | Dx = 1.541 Mg m−3 |
b = 12.546 (7) Å | Cu Kα radiation |
c = 5.3092 (16) Å | T = 300 K |
α = 51.074 (3)° |
Least-squares matrix: full | R(F2) = 0.00000 |
Rp = 0.073 | 1921 data points |
Rwp = 0.132 | 10 parameters |
Rexp = 0.013 | Background function: Background function: "chebyschev" function with 24 terms: 4846.854, -11028.729, -20160.862, 256317.539, 592987.724, -5.249158441e6, -3.631253229e6, 4.6716624983e7, 2.478157997e6, -2.22566966249e8, 5.3300222852e7, 6.38125053237e8, -2.55142761173e8, -1.156971410908e9, 5.82828782201e8, 1.333696204767e9, -7.80463244314e8, -9.38678820304e8, 6.25995183217e8, 3.54965933309e8, -2.79499578917e8, -4.3505635500e7, 5.3561337350e7, -6.779782588e6, |
x | y | z | Uiso*/Ueq | ||
H1 | 0.73437 | 0.64832 | 0.61697 | 0.010* | |
H3 | 0.62066 | 0.52561 | 0.48475 | 0.010* | |
H5 | 0.63637 | 0.70515 | 0.70368 | 0.010* | |
H7 | 0.39286 | 0.75947 | 0.76895 | 0.010* | |
H9 | 0.56380 | 0.71649 | 1.02060 | 0.010* | |
H11 | 0.57257 | 0.86694 | 0.60450 | 0.010* | |
H13 | 0.67816 | 0.42391 | 0.32840 | 0.010* | |
H15 | 0.78138 | 0.35187 | 0.24815 | 0.010* | |
C1 | 0.82279 | 0.46783 | 0.40575 | 0.010* | |
C3 | 0.74039 | 0.52654 | 0.46840 | 0.010* | |
C5 | 0.72384 | 0.44947 | 0.36647 | 0.010* | |
C7 | 0.70785 | 0.59186 | 0.54957 | 0.010* | |
C9 | 0.64674 | 0.58407 | 0.54803 | 0.010* | |
C11 | 0.61283 | 0.64767 | 0.63013 | 0.010* | |
C13 | 0.45912 | 0.67848 | 0.67324 | 0.010* | |
C15 | 0.48324 | 0.81449 | 0.82113 | 0.010* | |
C17 | 0.54189 | 0.77530 | 0.78740 | 0.010* | |
C19 | 0.77679 | 0.41206 | 0.32570 | 0.010* | |
N1 | 0.55450 | 0.63368 | 0.61499 | 0.010* | |
N3 | 0.52151 | 0.69179 | 0.69055 | 0.010* | |
N5 | 0.43833 | 0.75280 | 0.75654 | 0.010* | |
N7 | 0.88518 | 0.46110 | 0.41877 | 0.010* | |
O1 | 0.80179 | 0.53803 | 0.49165 | 0.010* | |
O3 | 0.90364 | 0.39190 | 0.35136 | 0.010* | |
O5 | 0.91767 | 0.52278 | 0.49571 | 0.010* | |
O7 | 0.42825 | 0.61607 | 0.60001 | 0.010* | |
O9 | 0.47708 | 0.88773 | 0.89374 | 0.010* | |
H17 | 0.04669 | 0.90902 | 0.96963 | 0.010* | |
H19 | 0.10363 | 0.76403 | 0.75563 | 0.010* | |
H21 | 0.15591 | 0.92637 | 0.99388 | 0.010* | |
H23 | 0.40287 | 0.90144 | 0.95446 | 0.010* | |
H25 | 0.24945 | 1.06139 | 0.86481 | 0.010* | |
H27 | 0.24527 | 0.90839 | 1.27639 | 0.010* | |
H29 | 0.00265 | 0.69269 | 0.64518 | 0.010* | |
H31 | −0.11852 | 0.68967 | 0.59237 | 0.010* | |
C21 | −0.10609 | 0.80451 | 0.77935 | 0.010* | |
C23 | −0.00865 | 0.81021 | 0.81570 | 0.010* | |
C25 | −0.02653 | 0.73908 | 0.69938 | 0.010* | |
C27 | 0.04779 | 0.85095 | 0.88210 | 0.010* | |
C29 | 0.10147 | 0.82288 | 0.84010 | 0.010* | |
C31 | 0.15694 | 0.86719 | 0.90797 | 0.010* | |
C33 | 0.31258 | 0.84759 | 0.89330 | 0.010* | |
C35 | 0.33497 | 0.98019 | 1.05233 | 0.010* | |
C37 | 0.26695 | 0.96216 | 1.03632 | 0.010* | |
C39 | −0.08910 | 0.73637 | 0.67384 | 0.010* | |
N9 | 0.20693 | 0.83653 | 0.86463 | 0.010* | |
N11 | 0.25843 | 0.88000 | 0.92881 | 0.010* | |
N13 | 0.35739 | 0.90881 | 0.96795 | 0.010* | |
N15 | −0.16289 | 0.83235 | 0.80984 | 0.010* | |
O11 | −0.05809 | 0.84979 | 0.86689 | 0.010* | |
O13 | −0.20670 | 0.79634 | 0.71446 | 0.010* | |
O15 | −0.16667 | 0.89097 | 0.92750 | 0.010* | |
O17 | 0.31939 | 0.77775 | 0.81175 | 0.010* | |
O19 | 0.36417 | 1.04487 | 1.12393 | 0.010* |
H1—C7 | 1.0828 | H17—C27 | 1.0853 |
H3—C9 | 1.0830 | H19—C29 | 1.0841 |
H5—C11 | 1.09 | H21—C31 | 1.0910 |
H7—N5 | 1.0308 | H23—O9 | 1.7392 |
H7—O17 | 1.7172 | H23—N13 | 1.0341 |
H9—C17 | 1.1006 | H25—C37 | 1.0961 |
H11—C17 | 1.0844 | H27—C37 | 1.0928 |
H13—C5 | 1.0744 | H29—C25 | 1.0773 |
H15—C19 | 1.0787 | H31—C39 | 1.0754 |
C1—C19 | 1.3678 | C21—C39 | 1.3734 |
C1—N7 | 1.3937 | C21—N15 | 1.3908 |
C1—O1 | 1.3512 | C21—O11 | 1.3466 |
C3—C5 | 1.3838 | C23—C25 | 1.3853 |
C3—C7 | 1.4127 | C23—C27 | 1.4084 |
C3—O1 | 1.3605 | C23—O11 | 1.3616 |
C5—H13 | 1.0744 | C25—H29 | 1.0773 |
C5—C3 | 1.3838 | C25—C23 | 1.3853 |
C5—C19 | 1.3905 | C25—C39 | 1.3877 |
C7—H1 | 1.0828 | C27—H17 | 1.0853 |
C7—C3 | 1.4127 | C27—C23 | 1.4084 |
C7—C9 | 1.3468 | C27—C29 | 1.3479 |
C9—H3 | 1.0830 | C29—H19 | 1.0841 |
C9—C7 | 1.3468 | C29—C27 | 1.3479 |
C9—C11 | 1.4167 | C29—C31 | 1.4134 |
C11—H5 | 1.09 | C31—H21 | 1.0910 |
C11—C9 | 1.4167 | C31—C29 | 1.4134 |
C11—N1 | 1.2898 | C31—N9 | 1.2920 |
C13—N3 | 1.3792 | C33—N11 | 1.3716 |
C13—N5 | 1.3858 | C33—N13 | 1.3760 |
C13—O7 | 1.2081 | C33—O17 | 1.2221 |
C15—C17 | 1.5026 | C35—C37 | 1.5041 |
C15—N5 | 1.3494 | C35—N13 | 1.3727 |
C15—O9 | 1.2217 | C35—O19 | 1.2075 |
C17—H9 | 1.1006 | C37—H25 | 1.0961 |
C17—H11 | 1.0844 | C37—H27 | 1.0928 |
C17—C15 | 1.5026 | C37—C35 | 1.5041 |
C17—N3 | 1.4510 | C37—N11 | 1.4511 |
C19—H15 | 1.0787 | C39—H31 | 1.0754 |
C19—C1 | 1.3678 | C39—C21 | 1.3734 |
C19—C5 | 1.3905 | C39—C25 | 1.3877 |
N1—C11 | 1.2898 | N9—C31 | 1.2920 |
N1—N3 | 1.3241 | N9—N11 | 1.3284 |
N3—C13 | 1.3792 | N11—C33 | 1.3716 |
N3—C17 | 1.4510 | N11—C37 | 1.4511 |
N3—N1 | 1.3241 | N11—N9 | 1.3284 |
N5—H7 | 1.0308 | N13—H23 | 1.0341 |
N5—C13 | 1.3858 | N13—C33 | 1.3760 |
N5—C15 | 1.3494 | N13—C35 | 1.3727 |
N7—C1 | 1.3937 | N15—C21 | 1.3908 |
N7—O3 | 1.2415 | N15—O13 | 1.2424 |
N7—O5 | 1.2322 | N15—O15 | 1.2390 |
O1—C1 | 1.3512 | O11—C21 | 1.3466 |
O1—C3 | 1.3605 | O11—C23 | 1.3616 |
O3—N7 | 1.2415 | O13—N15 | 1.2424 |
O5—N7 | 1.2322 | O15—N15 | 1.2390 |
O7—C13 | 1.2081 | O17—H7 | 1.7172 |
O9—C15 | 1.2217 | O17—C33 | 1.2221 |
O9—H23 | 1.7392 | O19—C35 | 1.2075 |
C19—C1—N7 | 131.106 | C39—C21—N15 | 131.144 |
C19—C1—O1 | 111.839 | C39—C21—O11 | 111.9 |
N7—C1—O1 | 117.038 | N15—C21—O11 | 116.955 |
C5—C3—C7 | 134.101 | C25—C23—C27 | 134.363 |
C5—C3—O1 | 109.435 | C25—C23—O11 | 109.899 |
C7—C3—O1 | 116.464 | C27—C23—O11 | 115.72 |
H13—C5—C3 | 125.354 | H29—C25—C23 | 126.248 |
H13—C5—C19 | 127.272 | H29—C25—C39 | 126.794 |
C3—C5—C19 | 107.374 | C23—C25—C39 | 106.941 |
H1—C7—C3 | 116.82 | H17—C27—C23 | 116.428 |
H1—C7—C9 | 120.819 | H17—C27—C29 | 119.78 |
C3—C7—C9 | 122.356 | C23—C27—C29 | 123.789 |
H3—C9—C7 | 120.134 | H19—C29—C27 | 121.082 |
H3—C9—C11 | 116.188 | H19—C29—C31 | 117.375 |
C7—C9—C11 | 123.672 | C27—C29—C31 | 121.539 |
H5—C11—C9 | 119.676 | H21—C31—C29 | 118.714 |
H5—C11—N1 | 122.828 | H21—C31—N9 | 122.561 |
C9—C11—N1 | 117.495 | C29—C31—N9 | 118.725 |
N3—C13—N5 | 105.705 | N11—C33—N13 | 106.558 |
N3—C13—O7 | 127.975 | N11—C33—O17 | 126.455 |
N5—C13—O7 | 126.319 | N13—C33—O17 | 126.987 |
C17—C15—N5 | 106.775 | C37—C35—N13 | 106.3 |
C17—C15—O9 | 126.879 | C37—C35—O19 | 126.98 |
N5—C15—O9 | 126.346 | N13—C35—O19 | 126.719 |
H9—C17—H11 | 109.402 | H25—C37—H27 | 108.787 |
H9—C17—C15 | 110.123 | H25—C37—C35 | 112.057 |
H11—C17—C15 | 110.441 | H27—C37—C35 | 109.642 |
H9—C17—N3 | 112.349 | H25—C37—N11 | 111.487 |
H11—C17—N3 | 112.096 | H27—C37—N11 | 112.44 |
C15—C17—N3 | 102.255 | C35—C37—N11 | 102.349 |
H15—C19—C1 | 126.564 | H31—C39—C21 | 126.816 |
H15—C19—C5 | 128.088 | H31—C39—C25 | 127.654 |
C1—C19—C5 | 105.348 | C21—C39—C25 | 105.524 |
C11—N1—N3 | 118.95 | C31—N9—N11 | 117.485 |
C13—N3—C17 | 111.706 | C33—N11—C37 | 111.818 |
C13—N3—N1 | 119.565 | C33—N11—N9 | 119.72 |
C17—N3—N1 | 128.71 | C37—N11—N9 | 128.461 |
H7—N5—C13 | 122.941 | H23—N13—C33 | 121.648 |
H7—N5—C15 | 123.529 | H23—N13—C35 | 125.396 |
C13—N5—C15 | 113.529 | C33—N13—C35 | 112.943 |
C1—N7—O3 | 116.476 | C21—N15—O13 | 116.843 |
C1—N7—O5 | 118.547 | C21—N15—O15 | 118.694 |
O3—N7—O5 | 124.977 | O13—N15—O15 | 124.462 |
C1—O1—C3 | 106.003 | C21—O11—C23 | 105.729 |