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The three title compounds, namely (Z)-1-(4,5-dinitroimidazol-1-yl)-3-morpholinopropan-2-one 2,4-dinitrophenylhydrazone, C16H17N9O9, (IV), (Z)-3-morpholino-1-(4-morpholino-5-nitroimidazol-1-yl)propan-2-one 2,4-dinitrophenylhydrazone, C20H25N9O8, (Va), and (E)-3-morpholino-1-(4-morpholino-5-nitroimidazol-1-yl)propan-2-one 2,4-dinitrophenylhydrazone tetrahydrofuran solvate, C20H25N9O8·C4H8O, (Vb), have been prepared and their structures determined. In (IV), the C-4 nitro group is nearly perpendicular to the imidazole ring and the C-4-NO2 bond length is comparable to the value for a normal single Csp2-NO2 bond. In (IV), (Va) and (Vb), the C-5 nitro group deviates insignificantly from the imidazole plane and the C-5-NO2 bond length is far shorter in all three compounds than C-4-NO2 in (IV). In consequence, the C-4 nitro group in (IV) is easily replaced by morpholine, while the C-5 nitro group in (IV), (Va) and (Vb) shows an extraordinary stability on treatment with the amine. The E configuration in (Vb) is stabilized by a three-centre hydrogen bond.
Supporting information
CCDC references: 163931; 163932; 163933
For all compounds, data collection: KM-4 Software (Kuma Diffraction, 1991); cell refinement: KM-4 Software; data reduction: KM-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
(IV) (
Z)-1-(4,5-dinitroimidazol-1-yl)-3-morpholinopropan-2-one
2,4-dinitrophenylhydrazone
top
Crystal data top
C16H17N9O9 | F(000) = 992 |
Mr = 479.39 | Dx = 1.551 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54178 Å |
a = 9.0382 (7) Å | Cell parameters from 49 reflections |
b = 19.2008 (13) Å | θ = 14.4–35.9° |
c = 11.9087 (8) Å | µ = 1.12 mm−1 |
β = 96.579 (6)° | T = 293 K |
V = 2053.0 (3) Å3 | Prism, yellow |
Z = 4 | 0.43 × 0.22 × 0.18 mm |
Data collection top
Kuma KM-4 diffractometer | Rint = 0.017 |
Radiation source: fine-focus sealed tube | θmax = 70.1°, θmin = 4.4° |
Graphite monochromator | h = −11→10 |
ω/2θ scans | k = 0→23 |
4027 measured reflections | l = 0→14 |
3851 independent reflections | 2 standard reflections every 100 reflections |
3135 reflections with I > 2σ(I) | intensity decay: 3.7% |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.127 | All H-atom parameters refined |
S = 1.08 | Calculated w = 1/[σ2(Fo2) + (0.0674P)2 + 0.5232P] where P = (Fo2 + 2Fc2)/3 |
3851 reflections | (Δ/σ)max < 0.001 |
375 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.25752 (15) | 0.65795 (8) | 1.11034 (11) | 0.0415 (3) | |
C2 | 0.2022 (2) | 0.71521 (11) | 1.15519 (17) | 0.0541 (5) | |
N3 | 0.2722 (2) | 0.73276 (8) | 1.25267 (15) | 0.0578 (4) | |
C4 | 0.37949 (19) | 0.68461 (9) | 1.27170 (14) | 0.0444 (4) | |
C5 | 0.37352 (18) | 0.63746 (9) | 1.18701 (13) | 0.0393 (4) | |
C6 | 0.2061 (2) | 0.62955 (12) | 0.99913 (15) | 0.0492 (4) | |
C7 | 0.29988 (17) | 0.65246 (9) | 0.90886 (14) | 0.0394 (4) | |
C8 | 0.41305 (19) | 0.70944 (9) | 0.93221 (15) | 0.0422 (4) | |
N9 | 0.28839 (15) | 0.62582 (8) | 0.81027 (12) | 0.0439 (3) | |
N10 | 0.18812 (17) | 0.57209 (8) | 0.78763 (13) | 0.0469 (4) | |
C11 | 0.19044 (17) | 0.53541 (9) | 0.69125 (13) | 0.0410 (4) | |
C12 | 0.10082 (18) | 0.47585 (9) | 0.66530 (15) | 0.0447 (4) | |
C13 | 0.1098 (2) | 0.43736 (10) | 0.56836 (16) | 0.0489 (4) | |
C14 | 0.2066 (2) | 0.45791 (10) | 0.49539 (16) | 0.0510 (4) | |
C15 | 0.2943 (2) | 0.51690 (11) | 0.51555 (17) | 0.0529 (4) | |
C16 | 0.2867 (2) | 0.55486 (10) | 0.61103 (15) | 0.0491 (4) | |
N17 | −0.00566 (19) | 0.45181 (10) | 0.73865 (14) | 0.0582 (4) | |
O18 | −0.01693 (17) | 0.48265 (9) | 0.82804 (13) | 0.0700 (4) | |
O19 | −0.0826 (2) | 0.40184 (12) | 0.70885 (17) | 0.1019 (7) | |
N20 | 0.2155 (2) | 0.41769 (11) | 0.39266 (17) | 0.0718 (5) | |
O21 | 0.1312 (3) | 0.36869 (11) | 0.37305 (19) | 0.1066 (7) | |
O22 | 0.3060 (3) | 0.43594 (13) | 0.33007 (18) | 0.1137 (8) | |
N23 | 0.54698 (14) | 0.68306 (7) | 0.99897 (11) | 0.0388 (3) | |
C24 | 0.6390 (2) | 0.74094 (11) | 1.04680 (18) | 0.0517 (5) | |
C25 | 0.7778 (2) | 0.71309 (16) | 1.1134 (2) | 0.0704 (7) | |
O26 | 0.86181 (15) | 0.67108 (11) | 1.04582 (16) | 0.0840 (6) | |
C27 | 0.7726 (2) | 0.61397 (15) | 1.0000 (3) | 0.0738 (7) | |
C28 | 0.6340 (2) | 0.63977 (11) | 0.92951 (18) | 0.0494 (4) | |
N29 | 0.4856 (2) | 0.68843 (10) | 1.37304 (14) | 0.0615 (5) | |
O30 | 0.4647 (3) | 0.65756 (14) | 1.45398 (16) | 0.1131 (8) | |
O31 | 0.5875 (3) | 0.72788 (17) | 1.36971 (19) | 0.1423 (12) | |
N32 | 0.4635 (2) | 0.57824 (9) | 1.17602 (15) | 0.0572 (4) | |
O33 | 0.5700 (2) | 0.57225 (12) | 1.24768 (17) | 0.1012 (7) | |
O34 | 0.4326 (2) | 0.53839 (8) | 1.09758 (16) | 0.0814 (5) | |
H2A | 0.121 (3) | 0.7411 (13) | 1.115 (2) | 0.072 (7)* | |
H6A | 0.206 (3) | 0.5790 (13) | 1.008 (2) | 0.067 (7)* | |
H6B | 0.104 (3) | 0.6484 (13) | 0.979 (2) | 0.074 (7)* | |
H8A | 0.371 (2) | 0.7485 (10) | 0.9772 (16) | 0.046 (5)* | |
H8B | 0.435 (2) | 0.7302 (10) | 0.8578 (17) | 0.048 (5)* | |
H10A | 0.130 (3) | 0.5591 (11) | 0.8327 (19) | 0.057 (6)* | |
H13A | 0.055 (3) | 0.3988 (13) | 0.5556 (18) | 0.061 (6)* | |
H15A | 0.360 (3) | 0.5293 (13) | 0.464 (2) | 0.074 (7)* | |
H16A | 0.351 (3) | 0.5942 (12) | 0.6306 (19) | 0.062 (6)* | |
H24A | 0.663 (2) | 0.7742 (12) | 0.9842 (19) | 0.061 (6)* | |
H24B | 0.586 (3) | 0.7672 (12) | 1.0971 (19) | 0.062 (6)* | |
H25A | 0.753 (3) | 0.6824 (12) | 1.180 (2) | 0.066 (7)* | |
H25B | 0.838 (3) | 0.7492 (14) | 1.147 (2) | 0.077 (7)* | |
H27A | 0.832 (3) | 0.5897 (14) | 0.945 (2) | 0.087 (8)* | |
H27B | 0.745 (3) | 0.5818 (15) | 1.063 (2) | 0.093 (9)* | |
H28A | 0.578 (2) | 0.6009 (11) | 0.9030 (17) | 0.050 (5)* | |
H28B | 0.650 (3) | 0.6671 (11) | 0.8631 (19) | 0.060 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0341 (7) | 0.0523 (8) | 0.0387 (7) | −0.0024 (6) | 0.0060 (5) | −0.0004 (6) |
C2 | 0.0470 (10) | 0.0615 (11) | 0.0560 (11) | 0.0128 (9) | 0.0145 (9) | 0.0004 (9) |
N3 | 0.0651 (11) | 0.0509 (9) | 0.0599 (10) | 0.0033 (8) | 0.0177 (8) | −0.0078 (7) |
C4 | 0.0433 (9) | 0.0506 (9) | 0.0402 (9) | −0.0126 (7) | 0.0090 (7) | −0.0020 (7) |
C5 | 0.0349 (8) | 0.0435 (8) | 0.0404 (8) | −0.0026 (6) | 0.0076 (6) | 0.0032 (7) |
C6 | 0.0386 (9) | 0.0691 (13) | 0.0399 (9) | −0.0122 (8) | 0.0041 (7) | −0.0012 (8) |
C7 | 0.0304 (8) | 0.0483 (9) | 0.0389 (8) | −0.0004 (6) | 0.0014 (6) | 0.0029 (7) |
C8 | 0.0394 (9) | 0.0442 (9) | 0.0428 (9) | −0.0026 (7) | 0.0039 (7) | 0.0032 (7) |
N9 | 0.0369 (7) | 0.0523 (8) | 0.0420 (8) | −0.0064 (6) | 0.0018 (6) | 0.0002 (6) |
N10 | 0.0387 (8) | 0.0612 (9) | 0.0411 (8) | −0.0117 (7) | 0.0050 (6) | −0.0026 (7) |
C11 | 0.0331 (8) | 0.0495 (9) | 0.0392 (8) | −0.0008 (7) | −0.0005 (6) | 0.0042 (7) |
C12 | 0.0357 (8) | 0.0513 (9) | 0.0459 (9) | −0.0035 (7) | −0.0008 (7) | 0.0075 (8) |
C13 | 0.0447 (10) | 0.0440 (9) | 0.0559 (11) | −0.0006 (8) | −0.0034 (8) | −0.0004 (8) |
C14 | 0.0501 (10) | 0.0506 (10) | 0.0510 (10) | 0.0072 (8) | 0.0004 (8) | −0.0058 (8) |
C15 | 0.0510 (10) | 0.0599 (11) | 0.0491 (10) | −0.0021 (9) | 0.0116 (8) | −0.0002 (9) |
C16 | 0.0480 (10) | 0.0526 (10) | 0.0472 (10) | −0.0100 (8) | 0.0083 (8) | −0.0010 (8) |
N17 | 0.0491 (9) | 0.0713 (11) | 0.0537 (10) | −0.0187 (8) | 0.0030 (7) | 0.0073 (8) |
O18 | 0.0604 (9) | 0.0886 (11) | 0.0643 (9) | −0.0198 (8) | 0.0209 (7) | 0.0002 (8) |
O19 | 0.1081 (15) | 0.1161 (15) | 0.0847 (12) | −0.0740 (13) | 0.0247 (11) | −0.0094 (11) |
N20 | 0.0758 (13) | 0.0704 (12) | 0.0702 (12) | 0.0098 (10) | 0.0124 (10) | −0.0212 (10) |
O21 | 0.1185 (17) | 0.0879 (13) | 0.1162 (16) | −0.0206 (12) | 0.0254 (13) | −0.0558 (12) |
O22 | 0.1310 (19) | 0.1294 (18) | 0.0902 (14) | −0.0242 (15) | 0.0531 (14) | −0.0446 (13) |
N23 | 0.0305 (7) | 0.0444 (7) | 0.0420 (7) | −0.0035 (5) | 0.0059 (5) | −0.0031 (6) |
C24 | 0.0413 (10) | 0.0582 (11) | 0.0565 (11) | −0.0099 (8) | 0.0095 (8) | −0.0160 (9) |
C25 | 0.0376 (10) | 0.0998 (18) | 0.0722 (15) | −0.0066 (11) | −0.0003 (10) | −0.0290 (14) |
O26 | 0.0305 (7) | 0.1152 (14) | 0.1062 (13) | −0.0015 (8) | 0.0077 (7) | −0.0403 (11) |
C27 | 0.0364 (10) | 0.0844 (16) | 0.1005 (19) | 0.0095 (10) | 0.0077 (11) | −0.0242 (15) |
C28 | 0.0377 (9) | 0.0535 (10) | 0.0593 (11) | −0.0057 (8) | 0.0148 (8) | −0.0127 (9) |
N29 | 0.0585 (10) | 0.0810 (12) | 0.0448 (9) | −0.0250 (9) | 0.0048 (7) | −0.0072 (8) |
O30 | 0.1150 (16) | 0.157 (2) | 0.0605 (10) | −0.0520 (15) | −0.0173 (10) | 0.0412 (12) |
O31 | 0.1189 (18) | 0.214 (3) | 0.0881 (14) | −0.114 (2) | −0.0140 (13) | 0.0025 (16) |
N32 | 0.0602 (10) | 0.0530 (9) | 0.0595 (10) | 0.0132 (8) | 0.0116 (8) | 0.0071 (8) |
O33 | 0.0874 (13) | 0.1199 (16) | 0.0908 (13) | 0.0512 (12) | −0.0141 (10) | 0.0138 (12) |
O34 | 0.1040 (13) | 0.0529 (8) | 0.0899 (12) | 0.0110 (9) | 0.0223 (10) | −0.0158 (8) |
Geometric parameters (Å, º) top
N1—C2 | 1.344 (2) | C14—N20 | 1.457 (3) |
N1—C5 | 1.367 (2) | C15—C16 | 1.359 (3) |
N1—C6 | 1.458 (2) | C15—H15A | 0.93 (3) |
C2—N3 | 1.301 (3) | C16—H16A | 0.97 (2) |
C2—H2A | 0.97 (3) | N17—O19 | 1.214 (2) |
N3—C4 | 1.340 (2) | N17—O18 | 1.233 (2) |
C4—C5 | 1.352 (2) | N20—O21 | 1.216 (3) |
C4—N29 | 1.455 (2) | N20—O22 | 1.220 (3) |
C5—N32 | 1.413 (2) | N23—C24 | 1.464 (2) |
C6—C7 | 1.509 (2) | N23—C28 | 1.464 (2) |
C6—H6A | 0.98 (2) | C24—C25 | 1.504 (3) |
C6—H6B | 0.99 (3) | C24—H24A | 1.02 (2) |
C7—N9 | 1.274 (2) | C24—H24B | 0.96 (2) |
C7—C8 | 1.502 (2) | C25—O26 | 1.420 (3) |
C8—N23 | 1.461 (2) | C25—H25A | 1.03 (2) |
C8—H8A | 1.02 (2) | C25—H25B | 0.94 (3) |
C8—H8B | 1.01 (2) | O26—C27 | 1.432 (3) |
N9—N10 | 1.379 (2) | C27—C28 | 1.509 (3) |
N10—C11 | 1.349 (2) | C27—H27A | 1.01 (3) |
N10—H10A | 0.83 (2) | C27—H27B | 1.03 (3) |
C11—C16 | 1.414 (2) | C28—H28A | 0.94 (2) |
C11—C12 | 1.415 (2) | C28—H28B | 0.97 (2) |
C12—C13 | 1.381 (3) | N29—O30 | 1.165 (2) |
C12—N17 | 1.447 (2) | N29—O31 | 1.197 (2) |
C13—C14 | 1.360 (3) | N32—O34 | 1.215 (2) |
C13—H13A | 0.90 (2) | N32—O33 | 1.217 (2) |
C14—C15 | 1.388 (3) | | |
| | | |
C2—N1—C5 | 105.17 (15) | C16—C15—H15A | 120.7 (15) |
C2—N1—C6 | 124.94 (16) | C14—C15—H15A | 119.3 (15) |
C5—N1—C6 | 129.74 (15) | C15—C16—C11 | 121.17 (18) |
N3—C2—N1 | 113.67 (18) | C15—C16—H16A | 122.2 (13) |
N3—C2—H2A | 124.8 (14) | C11—C16—H16A | 116.5 (13) |
N1—C2—H2A | 121.5 (14) | O19—N17—O18 | 122.07 (18) |
C2—N3—C4 | 103.92 (16) | O19—N17—C12 | 118.29 (18) |
N3—C4—C5 | 111.70 (16) | O18—N17—C12 | 119.63 (16) |
N3—C4—N29 | 120.06 (17) | O21—N20—O22 | 123.7 (2) |
C5—C4—N29 | 128.24 (17) | O21—N20—C14 | 118.5 (2) |
C4—C5—N1 | 105.53 (15) | O22—N20—C14 | 117.8 (2) |
C4—C5—N32 | 129.35 (16) | C8—N23—C24 | 110.30 (14) |
N1—C5—N32 | 125.12 (15) | C8—N23—C28 | 110.78 (14) |
N1—C6—C7 | 113.06 (14) | C24—N23—C28 | 109.45 (14) |
N1—C6—H6A | 105.8 (14) | N23—C24—C25 | 109.73 (18) |
C7—C6—H6A | 112.1 (14) | N23—C24—H24A | 110.4 (13) |
N1—C6—H6B | 105.9 (14) | C25—C24—H24A | 111.8 (13) |
C7—C6—H6B | 107.6 (14) | N23—C24—H24B | 109.9 (14) |
H6A—C6—H6B | 112 (2) | C25—C24—H24B | 107.9 (14) |
N9—C7—C8 | 116.43 (15) | H24A—C24—H24B | 107.0 (18) |
N9—C7—C6 | 123.13 (15) | O26—C25—C24 | 111.80 (18) |
C8—C7—C6 | 120.44 (15) | O26—C25—H25A | 106.7 (14) |
N23—C8—C7 | 110.64 (13) | C24—C25—H25A | 111.3 (14) |
N23—C8—H8A | 107.8 (11) | O26—C25—H25B | 109.6 (16) |
C7—C8—H8A | 110.1 (11) | C24—C25—H25B | 111.8 (16) |
N23—C8—H8B | 112.5 (11) | H25A—C25—H25B | 105 (2) |
C7—C8—H8B | 108.7 (11) | C25—O26—C27 | 109.66 (17) |
H8A—C8—H8B | 107.0 (15) | O26—C27—C28 | 110.8 (2) |
C7—N9—N10 | 117.57 (14) | O26—C27—H27A | 106.3 (16) |
C11—N10—N9 | 118.88 (15) | C28—C27—H27A | 105.0 (16) |
C11—N10—H10A | 117.8 (15) | O26—C27—H27B | 110.6 (17) |
N9—N10—H10A | 123.2 (15) | C28—C27—H27B | 110.7 (17) |
N10—C11—C16 | 120.51 (16) | H27A—C27—H27B | 113 (2) |
N10—C11—C12 | 122.93 (16) | N23—C28—C27 | 109.71 (17) |
C16—C11—C12 | 116.55 (16) | N23—C28—H28A | 109.9 (12) |
C13—C12—C11 | 121.89 (17) | C27—C28—H28A | 107.8 (12) |
C13—C12—N17 | 116.13 (17) | N23—C28—H28B | 107.1 (13) |
C11—C12—N17 | 121.98 (16) | C27—C28—H28B | 115.8 (14) |
C14—C13—C12 | 118.84 (18) | H28A—C28—H28B | 106.4 (17) |
C14—C13—H13A | 121.2 (15) | O30—N29—O31 | 123.2 (2) |
C12—C13—H13A | 119.9 (15) | O30—N29—C4 | 120.43 (17) |
C13—C14—C15 | 121.52 (18) | O31—N29—C4 | 116.18 (19) |
C13—C14—N20 | 118.96 (19) | O34—N32—O33 | 124.97 (19) |
C15—C14—N20 | 119.50 (19) | O34—N32—C5 | 119.62 (17) |
C16—C15—C14 | 120.00 (19) | O33—N32—C5 | 115.39 (18) |
| | | |
C5—N1—C2—N3 | 0.0 (2) | C13—C14—C15—C16 | 1.3 (3) |
C6—N1—C2—N3 | −175.99 (17) | N20—C14—C15—C16 | 179.91 (19) |
N1—C2—N3—C4 | 0.5 (2) | C14—C15—C16—C11 | 0.0 (3) |
C2—N3—C4—C5 | −0.8 (2) | N10—C11—C16—C15 | 177.54 (17) |
C2—N3—C4—N29 | 178.02 (17) | C12—C11—C16—C15 | −1.5 (3) |
N3—C4—C5—N1 | 0.87 (19) | C13—C12—N17—O19 | −2.6 (3) |
N29—C4—C5—N1 | −177.87 (16) | C11—C12—N17—O19 | 177.3 (2) |
N3—C4—C5—N32 | −178.40 (17) | C13—C12—N17—O18 | 178.20 (17) |
N29—C4—C5—N32 | 2.9 (3) | C11—C12—N17—O18 | −1.9 (3) |
C2—N1—C5—C4 | −0.52 (18) | C13—C14—N20—O21 | 3.2 (3) |
C6—N1—C5—C4 | 175.22 (16) | C15—C14—N20—O21 | −175.5 (2) |
C2—N1—C5—N32 | 178.78 (17) | C13—C14—N20—O22 | −178.0 (2) |
C6—N1—C5—N32 | −5.5 (3) | C15—C14—N20—O22 | 3.3 (3) |
C2—N1—C6—C7 | 96.5 (2) | C7—C8—N23—C24 | −164.91 (14) |
C5—N1—C6—C7 | −78.5 (2) | C7—C8—N23—C28 | 73.76 (18) |
N1—C6—C7—N9 | 169.24 (16) | C8—N23—C24—C25 | −178.91 (16) |
N1—C6—C7—C8 | −11.1 (2) | C28—N23—C24—C25 | −56.8 (2) |
N9—C7—C8—N23 | −102.43 (17) | N23—C24—C25—O26 | 58.2 (3) |
C6—C7—C8—N23 | 77.9 (2) | C24—C25—O26—C27 | −58.8 (3) |
C8—C7—N9—N10 | 178.28 (14) | C25—O26—C27—C28 | 58.9 (3) |
C6—C7—N9—N10 | −2.0 (2) | C8—N23—C28—C27 | 179.28 (17) |
C7—N9—N10—C11 | −169.32 (15) | C24—N23—C28—C27 | 57.4 (2) |
N9—N10—C11—C16 | −4.5 (2) | O26—C27—C28—N23 | −58.9 (3) |
N9—N10—C11—C12 | 174.50 (15) | N3—C4—N29—O30 | 94.2 (3) |
N10—C11—C12—C13 | −177.15 (16) | C5—C4—N29—O30 | −87.2 (3) |
C16—C11—C12—C13 | 1.9 (2) | N3—C4—N29—O31 | −81.2 (3) |
N10—C11—C12—N17 | 3.0 (3) | C5—C4—N29—O31 | 97.4 (3) |
C16—C11—C12—N17 | −178.03 (16) | C4—C5—N32—O34 | 173.61 (19) |
C11—C12—C13—C14 | −0.7 (3) | N1—C5—N32—O34 | −5.5 (3) |
N17—C12—C13—C14 | 179.20 (16) | C4—C5—N32—O33 | −7.6 (3) |
C12—C13—C14—C15 | −0.9 (3) | N1—C5—N32—O33 | 173.31 (19) |
C12—C13—C14—N20 | −179.56 (17) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N10—H10A···O18 | 0.83 (2) | 1.98 (2) | 2.611 (2) | 133 (2) |
C6—H6A···O34 | 0.98 (2) | 2.33 (2) | 2.842 (2) | 112.0 (18) |
C6—H6B···O26i | 0.99 (3) | 2.46 (3) | 3.320 (2) | 145.4 (19) |
C13—H13A···O19 | 0.90 (2) | 2.32 (2) | 2.637 (3) | 100.6 (16) |
C16—H16A···N9 | 0.98 (2) | 2.36 (2) | 2.735 (2) | 102.5 (16) |
Symmetry code: (i) x−1, y, z. |
(Va) (
Z)-1-(4-morpholino-5-nitroimidazol-1-yl)-3-morpholinopropan-2-one
2,4-dinitrophenylhydrazone
top
Crystal data top
C20H25N9O8 | Z = 2 |
Mr = 519.49 | F(000) = 544 |
Triclinic, P1 | Dx = 1.471 Mg m−3 |
a = 8.0664 (6) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 12.3698 (10) Å | Cell parameters from 38 reflections |
c = 13.2280 (13) Å | θ = 11.4–32.2° |
α = 111.282 (8)° | µ = 0.99 mm−1 |
β = 106.037 (7)° | T = 293 K |
γ = 90.735 (6)° | Prism, orange-brown |
V = 1172.55 (13) Å3 | 0.52 × 0.22 × 0.16 mm |
Data collection top
Kuma KM-4 diffractometer | Rint = 0.006 |
Radiation source: fine-focus sealed tube | θmax = 70.1°, θmin = 3.8° |
Graphite monochromator | h = −9→9 |
ω/2θ scans | k = −14→14 |
4407 measured reflections | l = −15→9 |
4205 independent reflections | 2 standard reflections every 100 reflections |
3575 reflections with I > 2σ(I) | intensity decay: 1.5% |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.106 | All H-atom parameters refined |
S = 1.04 | Calculated w = 1/[σ2(Fo2) + (0.0491P)2 + 0.3977P] where P = (Fo2 + 2Fc2)/3 |
4205 reflections | (Δ/σ)max < 0.001 |
434 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.73219 (17) | 1.07067 (11) | 0.30647 (11) | 0.0394 (3) | |
C2 | 0.6685 (2) | 1.11499 (15) | 0.22835 (15) | 0.0463 (4) | |
N3 | 0.67492 (19) | 1.22982 (12) | 0.26953 (12) | 0.0460 (3) | |
C4 | 0.75053 (19) | 1.26521 (14) | 0.38352 (13) | 0.0389 (3) | |
C5 | 0.79154 (19) | 1.16700 (14) | 0.40960 (13) | 0.0385 (3) | |
C6 | 0.7411 (2) | 0.94624 (14) | 0.28057 (15) | 0.0422 (4) | |
C7 | 0.5930 (2) | 0.88658 (14) | 0.29834 (13) | 0.0393 (3) | |
C8 | 0.4642 (2) | 0.95597 (15) | 0.34888 (14) | 0.0425 (4) | |
N9 | 0.56507 (18) | 0.77586 (12) | 0.26820 (12) | 0.0436 (3) | |
N10 | 0.67787 (19) | 0.70925 (12) | 0.21650 (12) | 0.0440 (3) | |
C11 | 0.6358 (2) | 0.59151 (14) | 0.17102 (13) | 0.0385 (3) | |
C12 | 0.7496 (2) | 0.51144 (14) | 0.13154 (13) | 0.0401 (4) | |
C13 | 0.7023 (2) | 0.39187 (15) | 0.08657 (14) | 0.0427 (4) | |
C14 | 0.5388 (2) | 0.34943 (14) | 0.07772 (13) | 0.0417 (4) | |
C15 | 0.4218 (2) | 0.42414 (15) | 0.11317 (15) | 0.0440 (4) | |
C16 | 0.4690 (2) | 0.54187 (15) | 0.15885 (15) | 0.0430 (4) | |
N17 | 0.92190 (19) | 0.55118 (14) | 0.13470 (13) | 0.0515 (4) | |
O18 | 0.9583 (2) | 0.65417 (13) | 0.15356 (15) | 0.0784 (5) | |
O19 | 1.02297 (19) | 0.47958 (15) | 0.11587 (17) | 0.0819 (5) | |
N20 | 0.4870 (2) | 0.22401 (13) | 0.02960 (12) | 0.0509 (4) | |
O21 | 0.5888 (2) | 0.15919 (12) | −0.00444 (13) | 0.0696 (4) | |
O22 | 0.3422 (2) | 0.18844 (13) | 0.02456 (15) | 0.0751 (4) | |
N23 | 0.34041 (16) | 0.98898 (12) | 0.26465 (12) | 0.0418 (3) | |
C24 | 0.2622 (3) | 1.09188 (16) | 0.31848 (18) | 0.0537 (5) | |
C25 | 0.1331 (3) | 1.1214 (2) | 0.2287 (2) | 0.0688 (6) | |
O26 | 0.00152 (17) | 1.02646 (14) | 0.15767 (13) | 0.0710 (4) | |
C27 | 0.0784 (3) | 0.9277 (2) | 0.1037 (2) | 0.0696 (6) | |
C28 | 0.2033 (2) | 0.89255 (17) | 0.19029 (16) | 0.0516 (4) | |
N29 | 0.77156 (18) | 1.38129 (12) | 0.45242 (12) | 0.0429 (3) | |
C30 | 0.7001 (3) | 1.45843 (15) | 0.39385 (16) | 0.0483 (4) | |
C31 | 0.7593 (3) | 1.58446 (17) | 0.47139 (19) | 0.0587 (5) | |
O32 | 0.71433 (18) | 1.61231 (11) | 0.57372 (12) | 0.0631 (4) | |
C33 | 0.7967 (3) | 1.54175 (19) | 0.63176 (18) | 0.0642 (5) | |
C34 | 0.7386 (3) | 1.41346 (18) | 0.56284 (16) | 0.0542 (5) | |
N35 | 0.88102 (17) | 1.15388 (13) | 0.50996 (12) | 0.0458 (3) | |
O36 | 0.97978 (18) | 1.23815 (13) | 0.58793 (12) | 0.0681 (4) | |
O37 | 0.85794 (18) | 1.05837 (12) | 0.51830 (11) | 0.0586 (3) | |
H2A | 0.621 (3) | 1.0625 (18) | 0.1504 (18) | 0.060 (6)* | |
H6A | 0.739 (2) | 0.9113 (15) | 0.2004 (16) | 0.044 (5)* | |
H6B | 0.854 (3) | 0.9345 (17) | 0.3272 (17) | 0.055 (5)* | |
H8A | 0.404 (2) | 0.9072 (16) | 0.3772 (15) | 0.046 (5)* | |
H8B | 0.525 (2) | 1.0270 (16) | 0.4113 (16) | 0.044 (5)* | |
H10A | 0.787 (3) | 0.738 (2) | 0.227 (2) | 0.074 (7)* | |
H13A | 0.784 (3) | 0.3422 (16) | 0.0594 (16) | 0.052 (5)* | |
H15A | 0.304 (3) | 0.3929 (17) | 0.1039 (17) | 0.056 (5)* | |
H16A | 0.392 (3) | 0.5946 (17) | 0.1850 (17) | 0.057 (5)* | |
H24A | 0.352 (3) | 1.156 (2) | 0.3630 (19) | 0.070 (6)* | |
H24B | 0.202 (3) | 1.0778 (18) | 0.3721 (18) | 0.061 (6)* | |
H25A | 0.192 (3) | 1.140 (2) | 0.183 (2) | 0.084 (8)* | |
H25B | 0.081 (4) | 1.189 (2) | 0.264 (2) | 0.093 (8)* | |
H27A | 0.144 (3) | 0.950 (2) | 0.062 (2) | 0.071 (7)* | |
H27B | −0.018 (4) | 0.864 (2) | 0.057 (2) | 0.093 (8)* | |
H28A | 0.251 (3) | 0.8224 (17) | 0.1480 (17) | 0.056 (5)* | |
H28B | 0.141 (3) | 0.8710 (18) | 0.2378 (19) | 0.065 (6)* | |
H30A | 0.743 (3) | 1.4382 (16) | 0.3261 (17) | 0.052 (5)* | |
H30B | 0.573 (3) | 1.4442 (17) | 0.3670 (17) | 0.058 (6)* | |
H31A | 0.886 (3) | 1.6000 (19) | 0.4900 (19) | 0.070 (6)* | |
H31B | 0.697 (3) | 1.6353 (19) | 0.4332 (18) | 0.066 (6)* | |
H33A | 0.762 (3) | 1.563 (2) | 0.702 (2) | 0.084 (7)* | |
H33B | 0.926 (3) | 1.557 (2) | 0.653 (2) | 0.075 (7)* | |
H34A | 0.801 (3) | 1.367 (2) | 0.604 (2) | 0.072 (7)* | |
H34B | 0.609 (3) | 1.3981 (18) | 0.5514 (18) | 0.064 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0435 (7) | 0.0400 (7) | 0.0372 (7) | 0.0059 (5) | 0.0123 (5) | 0.0174 (6) |
C2 | 0.0573 (10) | 0.0452 (9) | 0.0354 (9) | 0.0050 (7) | 0.0106 (7) | 0.0170 (7) |
N3 | 0.0575 (8) | 0.0440 (8) | 0.0363 (7) | 0.0048 (6) | 0.0102 (6) | 0.0178 (6) |
C4 | 0.0358 (7) | 0.0434 (8) | 0.0379 (8) | 0.0017 (6) | 0.0108 (6) | 0.0164 (7) |
C5 | 0.0356 (7) | 0.0450 (8) | 0.0354 (8) | 0.0033 (6) | 0.0086 (6) | 0.0172 (7) |
C6 | 0.0444 (9) | 0.0408 (8) | 0.0456 (9) | 0.0090 (7) | 0.0176 (7) | 0.0181 (7) |
C7 | 0.0410 (8) | 0.0435 (8) | 0.0356 (8) | 0.0071 (6) | 0.0112 (6) | 0.0177 (7) |
C8 | 0.0446 (9) | 0.0464 (9) | 0.0384 (8) | 0.0052 (7) | 0.0165 (7) | 0.0154 (7) |
N9 | 0.0449 (7) | 0.0439 (8) | 0.0454 (8) | 0.0088 (6) | 0.0167 (6) | 0.0185 (6) |
N10 | 0.0422 (7) | 0.0410 (7) | 0.0505 (8) | 0.0076 (6) | 0.0165 (6) | 0.0173 (6) |
C11 | 0.0409 (8) | 0.0411 (8) | 0.0366 (8) | 0.0075 (6) | 0.0101 (6) | 0.0195 (7) |
C12 | 0.0375 (8) | 0.0486 (9) | 0.0392 (8) | 0.0075 (7) | 0.0124 (6) | 0.0218 (7) |
C13 | 0.0467 (9) | 0.0476 (9) | 0.0389 (8) | 0.0137 (7) | 0.0148 (7) | 0.0206 (7) |
C14 | 0.0494 (9) | 0.0407 (8) | 0.0363 (8) | 0.0056 (7) | 0.0106 (7) | 0.0181 (7) |
C15 | 0.0399 (8) | 0.0499 (9) | 0.0451 (9) | 0.0040 (7) | 0.0119 (7) | 0.0220 (7) |
C16 | 0.0383 (8) | 0.0468 (9) | 0.0474 (9) | 0.0098 (7) | 0.0129 (7) | 0.0217 (7) |
N17 | 0.0441 (8) | 0.0602 (9) | 0.0523 (9) | 0.0069 (7) | 0.0198 (7) | 0.0199 (7) |
O18 | 0.0672 (9) | 0.0561 (9) | 0.1051 (12) | −0.0097 (7) | 0.0485 (9) | 0.0069 (8) |
O19 | 0.0527 (8) | 0.0879 (11) | 0.1270 (15) | 0.0280 (8) | 0.0462 (9) | 0.0510 (11) |
N20 | 0.0656 (10) | 0.0455 (8) | 0.0416 (8) | 0.0048 (7) | 0.0150 (7) | 0.0177 (6) |
O21 | 0.0967 (11) | 0.0471 (7) | 0.0720 (9) | 0.0164 (7) | 0.0443 (8) | 0.0165 (7) |
O22 | 0.0630 (9) | 0.0574 (8) | 0.0946 (12) | −0.0102 (7) | 0.0179 (8) | 0.0222 (8) |
N23 | 0.0370 (7) | 0.0442 (7) | 0.0451 (8) | 0.0055 (5) | 0.0150 (6) | 0.0160 (6) |
C24 | 0.0506 (10) | 0.0420 (9) | 0.0668 (12) | 0.0087 (8) | 0.0205 (9) | 0.0167 (9) |
C25 | 0.0559 (12) | 0.0678 (14) | 0.0952 (17) | 0.0204 (10) | 0.0273 (12) | 0.0416 (13) |
O26 | 0.0439 (7) | 0.0884 (11) | 0.0782 (10) | 0.0206 (7) | 0.0169 (7) | 0.0298 (8) |
C27 | 0.0469 (11) | 0.0908 (17) | 0.0578 (12) | 0.0138 (11) | 0.0102 (10) | 0.0170 (12) |
C28 | 0.0430 (9) | 0.0516 (10) | 0.0499 (10) | 0.0029 (7) | 0.0148 (8) | 0.0073 (8) |
N29 | 0.0458 (7) | 0.0419 (7) | 0.0400 (7) | 0.0031 (6) | 0.0123 (6) | 0.0149 (6) |
C30 | 0.0526 (10) | 0.0452 (9) | 0.0507 (10) | 0.0074 (7) | 0.0188 (8) | 0.0200 (8) |
C31 | 0.0596 (12) | 0.0467 (10) | 0.0700 (13) | 0.0048 (9) | 0.0245 (10) | 0.0189 (9) |
O32 | 0.0667 (9) | 0.0500 (7) | 0.0627 (8) | 0.0102 (6) | 0.0212 (7) | 0.0089 (6) |
C33 | 0.0677 (13) | 0.0626 (12) | 0.0475 (11) | 0.0079 (10) | 0.0132 (10) | 0.0073 (9) |
C34 | 0.0626 (12) | 0.0568 (11) | 0.0420 (10) | 0.0067 (9) | 0.0182 (8) | 0.0157 (8) |
N35 | 0.0375 (7) | 0.0598 (9) | 0.0413 (8) | 0.0097 (6) | 0.0097 (6) | 0.0222 (7) |
O36 | 0.0572 (8) | 0.0793 (10) | 0.0493 (8) | −0.0048 (7) | −0.0083 (6) | 0.0218 (7) |
O37 | 0.0674 (8) | 0.0638 (8) | 0.0559 (8) | 0.0187 (6) | 0.0174 (6) | 0.0363 (7) |
Geometric parameters (Å, º) top
N1—C2 | 1.326 (2) | N20—O21 | 1.216 (2) |
N1—C5 | 1.398 (2) | N20—O22 | 1.218 (2) |
N1—C6 | 1.458 (2) | N23—C28 | 1.459 (2) |
C2—N3 | 1.318 (2) | N23—C24 | 1.462 (2) |
C2—H2A | 0.96 (2) | C24—C25 | 1.507 (3) |
N3—C4 | 1.358 (2) | C24—H24A | 0.95 (2) |
C4—N29 | 1.371 (2) | C24—H24B | 1.02 (2) |
C4—C5 | 1.398 (2) | C25—O26 | 1.416 (3) |
C5—N35 | 1.393 (2) | C25—H25A | 0.95 (3) |
C6—C7 | 1.511 (2) | C25—H25B | 0.97 (3) |
C6—H6A | 0.985 (19) | O26—C27 | 1.421 (3) |
C6—H6B | 1.00 (2) | C27—C28 | 1.500 (3) |
C7—N9 | 1.277 (2) | C27—H27A | 0.96 (2) |
C7—C8 | 1.501 (2) | C27—H27B | 0.99 (3) |
C8—N23 | 1.460 (2) | C28—H28A | 0.99 (2) |
C8—H8A | 0.997 (19) | C28—H28B | 1.01 (2) |
C8—H8B | 0.966 (18) | N29—C30 | 1.465 (2) |
N9—N10 | 1.3887 (19) | N29—C34 | 1.469 (2) |
N10—C11 | 1.355 (2) | C30—C31 | 1.503 (3) |
N10—H10A | 0.90 (2) | C30—H30A | 1.00 (2) |
C11—C16 | 1.414 (2) | C30—H30B | 0.98 (2) |
C11—C12 | 1.418 (2) | C31—O32 | 1.421 (3) |
C12—C13 | 1.382 (2) | C31—H31A | 0.98 (2) |
C12—N17 | 1.453 (2) | C31—H31B | 1.00 (2) |
C13—C14 | 1.372 (2) | O32—C33 | 1.419 (3) |
C13—H13A | 0.96 (2) | C33—C34 | 1.505 (3) |
C14—C15 | 1.385 (2) | C33—H33A | 0.99 (3) |
C14—N20 | 1.451 (2) | C33—H33B | 1.00 (2) |
C15—C16 | 1.361 (2) | C34—H34A | 0.98 (2) |
C15—H15A | 0.98 (2) | C34—H34B | 1.02 (2) |
C16—H16A | 0.95 (2) | N35—O36 | 1.2366 (19) |
N17—O19 | 1.217 (2) | N35—O37 | 1.2421 (19) |
N17—O18 | 1.221 (2) | | |
| | | |
C2—N1—C5 | 105.40 (13) | C8—N23—C24 | 111.65 (14) |
C2—N1—C6 | 123.78 (14) | N23—C24—C25 | 109.88 (18) |
C5—N1—C6 | 130.74 (13) | N23—C24—H24A | 108.8 (14) |
N3—C2—N1 | 114.14 (15) | C25—C24—H24A | 109.9 (13) |
N3—C2—H2A | 127.1 (12) | N23—C24—H24B | 110.8 (12) |
N1—C2—H2A | 118.7 (12) | C25—C24—H24B | 110.0 (12) |
C2—N3—C4 | 105.76 (14) | H24A—C24—H24B | 107.4 (18) |
N3—C4—N29 | 120.30 (14) | O26—C25—C24 | 111.46 (18) |
N3—C4—C5 | 108.80 (14) | O26—C25—H25A | 108.7 (16) |
N29—C4—C5 | 130.88 (15) | C24—C25—H25A | 108.9 (16) |
N35—C5—N1 | 121.31 (14) | O26—C25—H25B | 109.6 (16) |
N35—C5—C4 | 132.72 (15) | C24—C25—H25B | 110.1 (16) |
N1—C5—C4 | 105.85 (13) | H25A—C25—H25B | 108 (2) |
N1—C6—C7 | 113.23 (13) | C25—O26—C27 | 109.50 (17) |
N1—C6—H6A | 106.2 (10) | O26—C27—C28 | 110.72 (18) |
C7—C6—H6A | 110.2 (10) | O26—C27—H27A | 108.0 (14) |
N1—C6—H6B | 110.0 (11) | C28—C27—H27A | 107.2 (14) |
C7—C6—H6B | 109.8 (11) | O26—C27—H27B | 106.2 (15) |
H6A—C6—H6B | 107.2 (15) | C28—C27—H27B | 109.6 (16) |
N9—C7—C8 | 115.96 (14) | H27A—C27—H27B | 115 (2) |
N9—C7—C6 | 123.18 (14) | N23—C28—C27 | 110.01 (18) |
C8—C7—C6 | 120.80 (14) | N23—C28—H28A | 111.7 (12) |
N23—C8—C7 | 110.63 (13) | C27—C28—H28A | 107.3 (11) |
N23—C8—H8A | 111.5 (11) | N23—C28—H28B | 109.0 (12) |
C7—C8—H8A | 107.8 (10) | C27—C28—H28B | 110.2 (12) |
N23—C8—H8B | 107.9 (11) | H28A—C28—H28B | 108.5 (17) |
C7—C8—H8B | 109.1 (11) | C4—N29—C30 | 114.86 (14) |
H8A—C8—H8B | 110.0 (15) | C4—N29—C34 | 118.69 (14) |
C7—N9—N10 | 117.09 (14) | C30—N29—C34 | 112.13 (15) |
C11—N10—N9 | 117.25 (14) | N29—C30—C31 | 110.52 (16) |
C11—N10—H10A | 118.3 (15) | N29—C30—H30A | 106.8 (11) |
N9—N10—H10A | 122.6 (15) | C31—C30—H30A | 110.8 (11) |
N10—C11—C16 | 120.13 (15) | N29—C30—H30B | 110.7 (12) |
N10—C11—C12 | 123.81 (15) | C31—C30—H30B | 110.0 (12) |
C16—C11—C12 | 116.05 (15) | H30A—C30—H30B | 108.0 (16) |
C13—C12—C11 | 122.04 (15) | O32—C31—C30 | 111.64 (16) |
C13—C12—N17 | 116.41 (14) | O32—C31—H31A | 109.2 (13) |
C11—C12—N17 | 121.54 (15) | C30—C31—H31A | 109.2 (13) |
C14—C13—C12 | 118.94 (15) | O32—C31—H31B | 105.8 (12) |
C14—C13—H13A | 122.9 (11) | C30—C31—H31B | 109.0 (13) |
C12—C13—H13A | 118.1 (11) | H31A—C31—H31B | 112.1 (18) |
C13—C14—C15 | 121.17 (15) | C33—O32—C31 | 108.87 (16) |
C13—C14—N20 | 119.44 (15) | O32—C33—C34 | 112.06 (17) |
C15—C14—N20 | 119.39 (15) | O32—C33—H33A | 106.4 (15) |
C16—C15—C14 | 119.94 (16) | C34—C33—H33A | 108.4 (15) |
C16—C15—H15A | 119.7 (12) | O32—C33—H33B | 111.4 (13) |
C14—C15—H15A | 120.4 (12) | C34—C33—H33B | 109.2 (13) |
C15—C16—C11 | 121.83 (15) | H33A—C33—H33B | 109 (2) |
C15—C16—H16A | 121.4 (12) | N29—C34—C33 | 109.72 (17) |
C11—C16—H16A | 116.8 (12) | N29—C34—H34A | 109.7 (14) |
O19—N17—O18 | 122.64 (16) | C33—C34—H34A | 110.3 (14) |
O19—N17—C12 | 118.43 (16) | N29—C34—H34B | 110.3 (12) |
O18—N17—C12 | 118.90 (15) | C33—C34—H34B | 108.1 (12) |
O21—N20—O22 | 122.90 (16) | H34A—C34—H34B | 108.7 (18) |
O21—N20—C14 | 118.91 (16) | O36—N35—O37 | 122.36 (15) |
O22—N20—C14 | 118.19 (15) | O36—N35—C5 | 118.72 (15) |
C28—N23—C8 | 110.78 (14) | O37—N35—C5 | 118.91 (14) |
C28—N23—C24 | 109.26 (14) | | |
| | | |
C5—N1—C2—N3 | −1.9 (2) | C12—C11—C16—C15 | 0.8 (2) |
C6—N1—C2—N3 | −179.00 (15) | C13—C12—N17—O19 | −11.7 (2) |
N1—C2—N3—C4 | 0.8 (2) | C11—C12—N17—O19 | 169.18 (17) |
C2—N3—C4—N29 | −177.97 (15) | C13—C12—N17—O18 | 166.65 (17) |
C2—N3—C4—C5 | 0.67 (18) | C11—C12—N17—O18 | −12.4 (3) |
C2—N1—C5—N35 | −174.39 (15) | C13—C14—N20—O21 | −1.7 (2) |
C6—N1—C5—N35 | 2.4 (2) | C15—C14—N20—O21 | 177.81 (16) |
C2—N1—C5—C4 | 2.16 (17) | C13—C14—N20—O22 | 178.69 (16) |
C6—N1—C5—C4 | 178.97 (15) | C15—C14—N20—O22 | −1.8 (2) |
N3—C4—C5—N35 | 174.22 (16) | C7—C8—N23—C28 | 81.26 (17) |
N29—C4—C5—N35 | −7.3 (3) | C7—C8—N23—C24 | −156.72 (15) |
N3—C4—C5—N1 | −1.78 (17) | C28—N23—C24—C25 | −56.0 (2) |
N29—C4—C5—N1 | 176.67 (16) | C8—N23—C24—C25 | −178.92 (16) |
C2—N1—C6—C7 | −98.34 (19) | N23—C24—C25—O26 | 57.9 (2) |
C5—N1—C6—C7 | 85.4 (2) | C24—C25—O26—C27 | −59.3 (3) |
N1—C6—C7—N9 | 171.61 (15) | C25—O26—C27—C28 | 59.9 (3) |
N1—C6—C7—C8 | −5.6 (2) | C8—N23—C28—C27 | −179.45 (15) |
N9—C7—C8—N23 | −100.75 (17) | C24—N23—C28—C27 | 57.1 (2) |
C6—C7—C8—N23 | 76.68 (19) | O26—C27—C28—N23 | −59.6 (2) |
C8—C7—N9—N10 | 177.17 (14) | N3—C4—N29—C30 | 2.6 (2) |
C6—C7—N9—N10 | −0.2 (2) | C5—C4—N29—C30 | −175.67 (16) |
C7—N9—N10—C11 | −171.55 (14) | N3—C4—N29—C34 | 139.26 (17) |
N9—N10—C11—C16 | 11.3 (2) | C5—C4—N29—C34 | −39.0 (3) |
N9—N10—C11—C12 | −169.78 (14) | C4—N29—C30—C31 | −169.12 (15) |
N10—C11—C12—C13 | 179.44 (15) | C34—N29—C30—C31 | 51.4 (2) |
C16—C11—C12—C13 | −1.6 (2) | N29—C30—C31—O32 | −56.2 (2) |
N10—C11—C12—N17 | −1.5 (2) | C30—C31—O32—C33 | 60.7 (2) |
C16—C11—C12—N17 | 177.38 (14) | C31—O32—C33—C34 | −61.4 (2) |
C11—C12—C13—C14 | 1.4 (2) | C4—N29—C34—C33 | 170.89 (16) |
N17—C12—C13—C14 | −177.71 (14) | C30—N29—C34—C33 | −51.4 (2) |
C12—C13—C14—C15 | −0.1 (2) | O32—C33—C34—N29 | 56.8 (2) |
C12—C13—C14—N20 | 179.41 (14) | N1—C5—N35—O36 | 155.78 (15) |
C13—C14—C15—C16 | −0.7 (3) | C4—C5—N35—O36 | −19.7 (3) |
N20—C14—C15—C16 | 179.73 (15) | N1—C5—N35—O37 | −24.7 (2) |
C14—C15—C16—C11 | 0.4 (3) | C4—C5—N35—O37 | 159.78 (17) |
N10—C11—C16—C15 | 179.73 (15) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N10—H10A···O18 | 0.90 (2) | 2.00 (2) | 2.635 (2) | 127 (2) |
N10—H10A···O36i | 0.90 (2) | 2.56 (2) | 3.087 (2) | 118.6 (18) |
C15—H15A···O19ii | 0.98 (2) | 2.54 (2) | 3.305 (2) | 134.9 (15) |
C27—H27B···O22iii | 0.99 (3) | 2.51 (3) | 3.373 (3) | 146 (2) |
C34—H34A···O36 | 0.98 (2) | 2.16 (2) | 2.979 (3) | 140.7 (19) |
C6—H6B···O37 | 1.00 (2) | 2.425 (19)) | 2.804 (2) | 101.8 (13) |
C13—H13A···O19 | 0.96 (2) | 2.315 (18) | 2.662 (2) | 100.4 (13) |
C16—H16A···N9 | 0.95 (2) | 2.339 (19) | 2.712 (2) | 102.8 (14) |
Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) x−1, y, z; (iii) −x, −y+1, −z. |
(Vb) (
E)-1-(4-morpholino-5-nitroimidazol-1-yl)-3-morpholinopropan-2-one
2,4-dinitrophenylhydrazone tetrahydrofuran solvate
top
Crystal data top
C20H25N9O8·C4H8O | F(000) = 1248 |
Mr = 591.59 | Dx = 1.384 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
a = 7.2885 (6) Å | Cell parameters from 48 reflections |
b = 27.686 (2) Å | θ = 10.2–28.2° |
c = 14.3642 (11) Å | µ = 0.91 mm−1 |
β = 101.707 (8)° | T = 293 K |
V = 2838.2 (4) Å3 | Prism, yellow |
Z = 4 | 0.48 × 0.22 × 0.16 mm |
Data collection top
Kuma KM-4 diffractometer | Rint = 0.041 |
Radiation source: fine-focus sealed tube | θmax = 70.1°, θmin = 3.2° |
Graphite monochromator | h = −8→8 |
ω/2θ scans | k = 0→33 |
5307 measured reflections | l = 0→17 |
5120 independent reflections | 2 standard reflections every 100 reflections |
3957 reflections with I > 2σ(I) | intensity decay: 2.3% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.046 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.154 | w = 1/[σ2(Fo2) + (0.0886P)2 + 0.7418P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
5120 reflections | Δρmax = 0.29 e Å−3 |
480 parameters | Δρmin = −0.26 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0018 (3) |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.1121 (2) | 0.69548 (6) | 1.08522 (12) | 0.0499 (4) | |
C2 | 0.0221 (3) | 0.68264 (9) | 1.15328 (17) | 0.0602 (5) | |
H2A | −0.106 (4) | 0.6812 (9) | 1.1404 (17) | 0.066 (7)* | |
N3 | 0.1319 (3) | 0.67271 (7) | 1.23545 (13) | 0.0591 (5) | |
C4 | 0.3087 (3) | 0.67921 (7) | 1.22124 (14) | 0.0470 (4) | |
C5 | 0.3001 (3) | 0.69378 (7) | 1.12786 (14) | 0.0460 (4) | |
C6 | 0.0212 (3) | 0.70581 (8) | 0.98759 (16) | 0.0555 (5) | |
H6A | 0.069 (4) | 0.7365 (11) | 0.9698 (18) | 0.076 (8)* | |
H6B | −0.121 (4) | 0.7073 (9) | 0.9868 (18) | 0.071 (7)* | |
C7 | 0.0499 (3) | 0.66694 (7) | 0.91831 (14) | 0.0465 (4) | |
C8 | −0.0201 (3) | 0.67836 (9) | 0.81489 (16) | 0.0579 (5) | |
H8A | −0.140 (4) | 0.6584 (9) | 0.7918 (18) | 0.070 (7)* | |
H8B | −0.044 (4) | 0.7121 (10) | 0.8058 (18) | 0.071 (7)* | |
N9 | 0.1215 (2) | 0.62758 (5) | 0.95407 (11) | 0.0463 (4) | |
N10 | 0.1480 (2) | 0.59195 (6) | 0.89081 (12) | 0.0484 (4) | |
H10A | 0.138 (4) | 0.6023 (9) | 0.8235 (19) | 0.074 (7)* | |
C11 | 0.2004 (3) | 0.54785 (6) | 0.92643 (13) | 0.0440 (4) | |
C12 | 0.2437 (3) | 0.50920 (7) | 0.86987 (14) | 0.0504 (5) | |
C13 | 0.2854 (3) | 0.46356 (7) | 0.90715 (16) | 0.0546 (5) | |
H13A | 0.315 (4) | 0.4364 (10) | 0.8647 (18) | 0.071 (7)* | |
C14 | 0.2896 (3) | 0.45574 (7) | 1.00123 (16) | 0.0540 (5) | |
C15 | 0.2543 (3) | 0.49279 (8) | 1.06065 (16) | 0.0539 (5) | |
H15A | 0.259 (4) | 0.4873 (9) | 1.1247 (18) | 0.066 (7)* | |
C16 | 0.2098 (3) | 0.53765 (7) | 1.02363 (15) | 0.0498 (5) | |
H16A | 0.188 (3) | 0.5630 (8) | 1.0628 (16) | 0.052 (6)* | |
N17 | 0.2525 (3) | 0.51526 (7) | 0.77067 (13) | 0.0656 (5) | |
O18 | 0.2275 (3) | 0.55514 (6) | 0.73499 (12) | 0.0806 (5) | |
O19 | 0.2858 (4) | 0.48048 (7) | 0.72570 (15) | 0.1124 (9) | |
N20 | 0.3347 (3) | 0.40767 (7) | 1.03980 (17) | 0.0691 (5) | |
O21 | 0.3558 (4) | 0.37516 (7) | 0.98588 (17) | 0.1009 (7) | |
O22 | 0.3472 (3) | 0.40182 (7) | 1.12488 (16) | 0.0962 (7) | |
N23 | 0.1065 (2) | 0.66360 (6) | 0.75425 (11) | 0.0498 (4) | |
C24 | 0.2820 (3) | 0.69039 (9) | 0.77605 (16) | 0.0610 (6) | |
H24A | 0.345 (4) | 0.6829 (9) | 0.8402 (19) | 0.069 (7)* | |
H24B | 0.259 (3) | 0.7271 (9) | 0.7716 (17) | 0.065 (7)* | |
C25 | 0.4054 (4) | 0.67636 (13) | 0.70876 (19) | 0.0752 (7) | |
H25A | 0.508 (5) | 0.6950 (11) | 0.722 (2) | 0.084 (9)* | |
H25B | 0.428 (3) | 0.6430 (10) | 0.7146 (17) | 0.060 (7)* | |
O26 | 0.3173 (3) | 0.68507 (7) | 0.61315 (12) | 0.0783 (5) | |
C27 | 0.1506 (5) | 0.65728 (11) | 0.59126 (18) | 0.0759 (7) | |
H27A | 0.181 (4) | 0.6235 (10) | 0.5974 (18) | 0.070 (7)* | |
H27B | 0.094 (4) | 0.6639 (11) | 0.529 (2) | 0.092 (9)* | |
C28 | 0.0181 (4) | 0.67064 (10) | 0.65387 (16) | 0.0654 (6) | |
H28A | −0.015 (4) | 0.7043 (12) | 0.648 (2) | 0.092 (9)* | |
H28B | −0.088 (4) | 0.6518 (10) | 0.6421 (19) | 0.077 (8)* | |
N29 | 0.4603 (2) | 0.67297 (6) | 1.29370 (11) | 0.0510 (4) | |
C30 | 0.4251 (4) | 0.66881 (11) | 1.38966 (16) | 0.0619 (6) | |
H30A | 0.376 (4) | 0.6374 (10) | 1.3960 (18) | 0.071 (7)* | |
H30B | 0.338 (4) | 0.6923 (9) | 1.3949 (17) | 0.065 (7)* | |
C31 | 0.6037 (4) | 0.67689 (15) | 1.45917 (19) | 0.0862 (9) | |
H31A | 0.640 (5) | 0.7126 (13) | 1.451 (2) | 0.102 (11)* | |
H31B | 0.598 (4) | 0.6712 (11) | 1.530 (2) | 0.096 (9)* | |
O32 | 0.7439 (3) | 0.64355 (10) | 1.44543 (13) | 0.1021 (8) | |
C33 | 0.7824 (4) | 0.64937 (15) | 1.35289 (19) | 0.0880 (10) | |
H33A | 0.879 (4) | 0.6236 (11) | 1.342 (2) | 0.086 (8)* | |
H33B | 0.819 (5) | 0.6877 (12) | 1.341 (2) | 0.102 (11)* | |
C34 | 0.6102 (3) | 0.64076 (9) | 1.27819 (17) | 0.0611 (6) | |
H34A | 0.631 (3) | 0.6454 (9) | 1.2142 (19) | 0.066 (7)* | |
H34B | 0.577 (4) | 0.6052 (11) | 1.281 (2) | 0.090 (9)* | |
N35 | 0.4393 (2) | 0.71253 (6) | 1.08388 (12) | 0.0493 (4) | |
O36 | 0.5983 (2) | 0.71781 (6) | 1.13290 (12) | 0.0645 (4) | |
O37 | 0.3992 (2) | 0.72388 (6) | 0.99953 (11) | 0.0641 (4) | |
O38 | 0.1803 (5) | 0.49375 (11) | 0.2749 (2) | 0.1338 (10) | |
C39 | 0.2463 (9) | 0.45782 (18) | 0.3413 (4) | 0.1502 (19) | |
H39A | 0.3779 | 0.4516 | 0.3429 | 0.180* | |
H39B | 0.1769 | 0.4281 | 0.3246 | 0.180* | |
C40 | 0.2215 (16) | 0.4744 (3) | 0.4300 (4) | 0.232 (4) | |
H40A | 0.3293 | 0.4664 | 0.4792 | 0.278* | |
H40B | 0.1107 | 0.4601 | 0.4463 | 0.278* | |
C41 | 0.1998 (14) | 0.5275 (3) | 0.4192 (5) | 0.206 (3) | |
H41A | 0.0809 | 0.5379 | 0.4328 | 0.247* | |
H41B | 0.3003 | 0.5442 | 0.4617 | 0.247* | |
C42 | 0.2072 (9) | 0.53680 (18) | 0.3225 (5) | 0.154 (2) | |
H42A | 0.1102 | 0.5596 | 0.2951 | 0.185* | |
H42B | 0.3279 | 0.5504 | 0.3183 | 0.185* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0459 (9) | 0.0503 (9) | 0.0543 (9) | 0.0052 (7) | 0.0117 (7) | −0.0074 (7) |
C2 | 0.0452 (13) | 0.0716 (14) | 0.0667 (14) | −0.0008 (10) | 0.0179 (10) | −0.0081 (11) |
N3 | 0.0493 (11) | 0.0713 (11) | 0.0614 (11) | −0.0024 (8) | 0.0223 (8) | −0.0028 (8) |
C4 | 0.0461 (11) | 0.0444 (9) | 0.0537 (11) | 0.0018 (8) | 0.0176 (8) | −0.0058 (8) |
C5 | 0.0438 (11) | 0.0438 (9) | 0.0523 (10) | 0.0021 (7) | 0.0144 (8) | −0.0046 (8) |
C6 | 0.0557 (14) | 0.0501 (11) | 0.0591 (12) | 0.0128 (9) | 0.0075 (9) | −0.0009 (9) |
C7 | 0.0431 (10) | 0.0439 (9) | 0.0519 (10) | 0.0020 (7) | 0.0079 (8) | 0.0018 (8) |
C8 | 0.0572 (14) | 0.0581 (13) | 0.0561 (12) | 0.0106 (10) | 0.0066 (10) | 0.0064 (10) |
N9 | 0.0481 (9) | 0.0420 (8) | 0.0485 (8) | 0.0028 (6) | 0.0092 (7) | −0.0014 (6) |
N10 | 0.0582 (10) | 0.0407 (8) | 0.0462 (9) | 0.0051 (7) | 0.0104 (7) | −0.0007 (6) |
C11 | 0.0385 (10) | 0.0416 (9) | 0.0508 (10) | −0.0007 (7) | 0.0066 (7) | 0.0012 (7) |
C12 | 0.0509 (11) | 0.0454 (10) | 0.0554 (11) | 0.0017 (8) | 0.0116 (9) | −0.0017 (8) |
C13 | 0.0485 (12) | 0.0457 (10) | 0.0688 (13) | 0.0034 (8) | 0.0102 (9) | −0.0025 (9) |
C14 | 0.0426 (11) | 0.0439 (10) | 0.0732 (14) | 0.0023 (8) | 0.0060 (9) | 0.0093 (9) |
C15 | 0.0486 (12) | 0.0555 (11) | 0.0555 (12) | 0.0003 (9) | 0.0056 (9) | 0.0099 (9) |
C16 | 0.0474 (11) | 0.0480 (10) | 0.0535 (11) | 0.0025 (8) | 0.0092 (8) | 0.0010 (9) |
N17 | 0.0861 (14) | 0.0543 (10) | 0.0601 (11) | 0.0103 (9) | 0.0239 (10) | −0.0034 (8) |
O18 | 0.1287 (16) | 0.0575 (9) | 0.0612 (10) | 0.0091 (10) | 0.0326 (10) | 0.0039 (7) |
O19 | 0.194 (3) | 0.0744 (12) | 0.0812 (13) | 0.0399 (14) | 0.0562 (16) | −0.0084 (10) |
N20 | 0.0621 (12) | 0.0528 (11) | 0.0886 (15) | 0.0045 (9) | 0.0060 (10) | 0.0163 (10) |
O21 | 0.1301 (19) | 0.0478 (10) | 0.1218 (17) | 0.0204 (10) | 0.0187 (14) | 0.0039 (10) |
O22 | 0.1158 (17) | 0.0744 (12) | 0.0950 (15) | 0.0190 (11) | 0.0134 (12) | 0.0337 (11) |
N23 | 0.0550 (10) | 0.0470 (8) | 0.0459 (9) | −0.0009 (7) | 0.0069 (7) | 0.0054 (7) |
C24 | 0.0654 (15) | 0.0602 (13) | 0.0552 (12) | −0.0113 (10) | 0.0066 (10) | 0.0078 (10) |
C25 | 0.0704 (17) | 0.091 (2) | 0.0653 (15) | −0.0112 (15) | 0.0169 (12) | 0.0172 (14) |
O26 | 0.0855 (13) | 0.0919 (12) | 0.0607 (10) | −0.0145 (10) | 0.0226 (9) | 0.0175 (9) |
C27 | 0.098 (2) | 0.0811 (18) | 0.0488 (13) | −0.0124 (15) | 0.0145 (13) | 0.0059 (12) |
C28 | 0.0709 (16) | 0.0701 (15) | 0.0508 (12) | −0.0077 (12) | 0.0018 (11) | 0.0101 (10) |
N29 | 0.0491 (10) | 0.0591 (10) | 0.0475 (9) | 0.0087 (7) | 0.0163 (7) | −0.0043 (7) |
C30 | 0.0630 (15) | 0.0759 (16) | 0.0508 (12) | 0.0070 (12) | 0.0213 (10) | −0.0050 (11) |
C31 | 0.0678 (17) | 0.138 (3) | 0.0531 (14) | 0.0227 (17) | 0.0133 (12) | −0.0179 (16) |
O32 | 0.0830 (13) | 0.166 (2) | 0.0564 (10) | 0.0498 (14) | 0.0132 (9) | 0.0063 (12) |
C33 | 0.0656 (17) | 0.140 (3) | 0.0602 (15) | 0.0383 (18) | 0.0159 (12) | 0.0001 (16) |
C34 | 0.0664 (15) | 0.0659 (14) | 0.0554 (12) | 0.0229 (11) | 0.0228 (10) | 0.0012 (10) |
N35 | 0.0501 (10) | 0.0445 (8) | 0.0566 (10) | 0.0006 (7) | 0.0182 (8) | −0.0027 (7) |
O36 | 0.0452 (9) | 0.0729 (10) | 0.0777 (10) | −0.0012 (7) | 0.0177 (7) | 0.0041 (8) |
O37 | 0.0783 (11) | 0.0627 (9) | 0.0546 (9) | −0.0101 (7) | 0.0210 (8) | 0.0021 (7) |
O38 | 0.194 (3) | 0.108 (2) | 0.1058 (18) | −0.0040 (19) | 0.045 (2) | 0.0038 (16) |
C39 | 0.206 (6) | 0.108 (3) | 0.139 (4) | 0.021 (3) | 0.043 (4) | 0.015 (3) |
C40 | 0.389 (14) | 0.180 (7) | 0.112 (4) | −0.050 (7) | 0.017 (6) | 0.027 (4) |
C41 | 0.320 (11) | 0.164 (6) | 0.134 (5) | −0.022 (6) | 0.046 (6) | −0.039 (4) |
C42 | 0.202 (6) | 0.101 (3) | 0.174 (5) | −0.038 (3) | 0.069 (4) | −0.018 (3) |
Geometric parameters (Å, º) top
N1—C2 | 1.331 (3) | C24—H24B | 1.03 (3) |
N1—C5 | 1.384 (3) | C25—O26 | 1.414 (3) |
N1—C6 | 1.453 (3) | C25—H25A | 0.90 (3) |
C2—N3 | 1.314 (3) | C25—H25B | 0.94 (3) |
C2—H2A | 0.91 (3) | O26—C27 | 1.419 (4) |
N3—C4 | 1.357 (3) | C27—C28 | 1.493 (4) |
C4—N29 | 1.367 (3) | C27—H27A | 0.96 (3) |
C4—C5 | 1.390 (3) | C27—H27B | 0.92 (3) |
C5—N35 | 1.399 (3) | C28—H28A | 0.96 (3) |
C6—C7 | 1.509 (3) | C28—H28B | 0.92 (3) |
C6—H6A | 0.97 (3) | N29—C30 | 1.457 (3) |
C6—H6B | 1.04 (3) | N29—C34 | 1.462 (3) |
C7—N9 | 1.271 (2) | C30—C31 | 1.488 (4) |
C7—C8 | 1.503 (3) | C30—H30A | 0.95 (3) |
C8—N23 | 1.450 (3) | C30—H30B | 0.92 (3) |
C8—H8A | 1.03 (3) | C31—O32 | 1.420 (4) |
C8—H8B | 0.95 (3) | C31—H31A | 1.04 (3) |
N9—N10 | 1.381 (2) | C31—H31B | 1.03 (3) |
N10—C11 | 1.349 (2) | O32—C33 | 1.422 (3) |
N10—H10A | 1.00 (3) | C33—C34 | 1.496 (4) |
C11—C16 | 1.413 (3) | C33—H33A | 1.03 (3) |
C11—C12 | 1.417 (3) | C33—H33B | 1.12 (3) |
C12—C13 | 1.382 (3) | C34—H34A | 0.97 (3) |
C12—N17 | 1.449 (3) | C34—H34B | 1.02 (3) |
C13—C14 | 1.363 (3) | N35—O37 | 1.228 (2) |
C13—H13A | 1.02 (3) | N35—O36 | 1.237 (2) |
C14—C15 | 1.391 (3) | O38—C42 | 1.369 (5) |
C14—N20 | 1.453 (3) | O38—C39 | 1.395 (5) |
C15—C16 | 1.364 (3) | C39—C40 | 1.400 (9) |
C15—H15A | 0.93 (2) | C39—H39A | 0.9700 |
C16—H16A | 0.93 (2) | C39—H39B | 0.9700 |
N17—O19 | 1.211 (2) | C40—C41 | 1.484 (10) |
N17—O18 | 1.215 (2) | C40—H40A | 0.9700 |
N20—O21 | 1.217 (3) | C40—H40B | 0.9700 |
N20—O22 | 1.218 (3) | C41—C42 | 1.423 (8) |
N23—C24 | 1.457 (3) | C41—H41A | 0.9700 |
N23—C28 | 1.468 (3) | C41—H41B | 0.9700 |
C24—C25 | 1.499 (4) | C42—H42A | 0.9700 |
C24—H24A | 0.97 (3) | C42—H42B | 0.9700 |
| | | |
C2—N1—C5 | 104.89 (18) | H25A—C25—H25B | 115 (3) |
C2—N1—C6 | 124.4 (2) | C25—O26—C27 | 108.8 (2) |
C5—N1—C6 | 130.59 (18) | O26—C27—C28 | 111.2 (2) |
N3—C2—N1 | 114.5 (2) | O26—C27—H27A | 109.7 (16) |
N3—C2—H2A | 125.7 (16) | C28—C27—H27A | 110.6 (16) |
N1—C2—H2A | 119.8 (16) | O26—C27—H27B | 108 (2) |
C2—N3—C4 | 105.13 (18) | C28—C27—H27B | 108 (2) |
N3—C4—N29 | 120.97 (18) | H27A—C27—H27B | 110 (2) |
N3—C4—C5 | 109.00 (18) | N23—C28—C27 | 110.5 (2) |
N29—C4—C5 | 129.98 (19) | N23—C28—H28A | 105.6 (18) |
N1—C5—C4 | 106.46 (17) | C27—C28—H28A | 111.7 (18) |
N1—C5—N35 | 122.09 (17) | N23—C28—H28B | 106.8 (17) |
C4—C5—N35 | 130.45 (18) | C27—C28—H28B | 111.8 (17) |
N1—C6—C7 | 113.54 (16) | H28A—C28—H28B | 110 (3) |
N1—C6—H6A | 107.9 (16) | C4—N29—C30 | 117.38 (18) |
C7—C6—H6A | 110.2 (15) | C4—N29—C34 | 118.36 (17) |
N1—C6—H6B | 106.1 (14) | C30—N29—C34 | 112.13 (18) |
C7—C6—H6B | 107.1 (14) | N29—C30—C31 | 109.0 (2) |
H6A—C6—H6B | 112 (2) | N29—C30—H30A | 107.8 (16) |
N9—C7—C8 | 127.52 (18) | C31—C30—H30A | 111.7 (16) |
N9—C7—C6 | 116.46 (18) | N29—C30—H30B | 106.1 (15) |
C8—C7—C6 | 115.92 (17) | C31—C30—H30B | 111.2 (16) |
N23—C8—C7 | 113.86 (18) | H30A—C30—H30B | 111 (2) |
N23—C8—H8A | 104.8 (14) | O32—C31—C30 | 111.4 (2) |
C7—C8—H8A | 107.5 (14) | O32—C31—H31A | 113 (2) |
N23—C8—H8B | 108.3 (16) | C30—C31—H31A | 105.9 (19) |
C7—C8—H8B | 110.9 (16) | O32—C31—H31B | 102.1 (18) |
H8A—C8—H8B | 111 (2) | C30—C31—H31B | 115.5 (19) |
C7—N9—N10 | 116.58 (16) | H31A—C31—H31B | 109 (2) |
C11—N10—N9 | 117.62 (16) | C31—O32—C33 | 109.9 (2) |
C11—N10—H10A | 126.0 (15) | O32—C33—C34 | 110.9 (2) |
N9—N10—H10A | 116.1 (15) | O32—C33—H33A | 109.0 (16) |
N10—C11—C16 | 120.60 (17) | C34—C33—H33A | 106.4 (17) |
N10—C11—C12 | 123.02 (17) | O32—C33—H33B | 110.6 (18) |
C16—C11—C12 | 116.36 (17) | C34—C33—H33B | 103.3 (18) |
C13—C12—C11 | 121.70 (19) | H33A—C33—H33B | 116 (3) |
C13—C12—N17 | 115.88 (18) | N29—C34—C33 | 109.7 (2) |
C11—C12—N17 | 122.39 (17) | N29—C34—H34A | 109.1 (15) |
C14—C13—C12 | 119.2 (2) | C33—C34—H34A | 113.1 (15) |
C14—C13—H13A | 120.7 (15) | N29—C34—H34B | 113.2 (18) |
C12—C13—H13A | 120.1 (15) | C33—C34—H34B | 107.4 (17) |
C13—C14—C15 | 121.43 (19) | H34A—C34—H34B | 104 (2) |
C13—C14—N20 | 118.8 (2) | O37—N35—O36 | 122.66 (17) |
C15—C14—N20 | 119.8 (2) | O37—N35—C5 | 119.40 (18) |
C16—C15—C14 | 119.4 (2) | O36—N35—C5 | 117.93 (17) |
C16—C15—H15A | 119.7 (15) | C42—O38—C39 | 106.5 (4) |
C14—C15—H15A | 120.9 (15) | O38—C39—C40 | 107.4 (5) |
C15—C16—C11 | 121.8 (2) | O38—C39—H39A | 110.2 |
C15—C16—H16A | 120.4 (13) | C40—C39—H39A | 110.2 |
C11—C16—H16A | 117.8 (13) | O38—C39—H39B | 110.2 |
O19—N17—O18 | 121.8 (2) | C40—C39—H39B | 110.2 |
O19—N17—C12 | 119.09 (19) | H39A—C39—H39B | 108.5 |
O18—N17—C12 | 119.14 (17) | C39—C40—C41 | 105.1 (5) |
O21—N20—O22 | 123.1 (2) | C39—C40—H40A | 110.7 |
O21—N20—C14 | 118.8 (2) | C41—C40—H40A | 110.7 |
O22—N20—C14 | 118.0 (2) | C39—C40—H40B | 110.7 |
C8—N23—C24 | 111.44 (18) | C41—C40—H40B | 110.7 |
C8—N23—C28 | 110.28 (18) | H40A—C40—H40B | 108.8 |
C24—N23—C28 | 109.55 (17) | C42—C41—C40 | 104.9 (5) |
N23—C24—C25 | 110.2 (2) | C42—C41—H41A | 110.8 |
N23—C24—H24A | 108.7 (16) | C40—C41—H41A | 110.8 |
C25—C24—H24A | 109.3 (16) | C42—C41—H41B | 110.8 |
N23—C24—H24B | 111.5 (14) | C40—C41—H41B | 110.8 |
C25—C24—H24B | 109.1 (14) | H41A—C41—H41B | 108.8 |
H24A—C24—H24B | 108 (2) | O38—C42—C41 | 107.5 (4) |
O26—C25—C24 | 111.6 (2) | O38—C42—H42A | 110.2 |
O26—C25—H25A | 107.9 (19) | C41—C42—H42A | 110.2 |
C24—C25—H25A | 107 (2) | O38—C42—H42B | 110.2 |
O26—C25—H25B | 106.9 (15) | C41—C42—H42B | 110.2 |
C24—C25—H25B | 108.3 (15) | H42A—C42—H42B | 108.5 |
| | | |
C5—N1—C2—N3 | −0.1 (3) | C11—C12—N17—O19 | −178.2 (3) |
C6—N1—C2—N3 | 176.86 (19) | C13—C12—N17—O18 | −176.0 (2) |
N1—C2—N3—C4 | −0.3 (3) | C11—C12—N17—O18 | 2.2 (3) |
C2—N3—C4—N29 | 178.49 (19) | C13—C14—N20—O21 | −4.6 (3) |
C2—N3—C4—C5 | 0.5 (2) | C15—C14—N20—O21 | 176.4 (2) |
C2—N1—C5—C4 | 0.4 (2) | C13—C14—N20—O22 | 176.3 (2) |
C6—N1—C5—C4 | −176.28 (18) | C15—C14—N20—O22 | −2.8 (3) |
C2—N1—C5—N35 | −169.24 (18) | C7—C8—N23—C24 | −65.0 (2) |
C6—N1—C5—N35 | 14.1 (3) | C7—C8—N23—C28 | 173.15 (19) |
N3—C4—C5—N1 | −0.6 (2) | C8—N23—C24—C25 | −176.84 (19) |
N29—C4—C5—N1 | −178.32 (18) | C28—N23—C24—C25 | −54.5 (3) |
N3—C4—C5—N35 | 167.88 (19) | N23—C24—C25—O26 | 58.6 (3) |
N29—C4—C5—N35 | −9.8 (3) | C24—C25—O26—C27 | −60.4 (3) |
C2—N1—C6—C7 | −107.1 (2) | C25—O26—C27—C28 | 60.3 (3) |
C5—N1—C6—C7 | 69.0 (3) | C8—N23—C28—C27 | 177.8 (2) |
N1—C6—C7—N9 | 10.8 (3) | C24—N23—C28—C27 | 54.8 (3) |
N1—C6—C7—C8 | −172.62 (19) | O26—C27—C28—N23 | −58.4 (3) |
N9—C7—C8—N23 | −45.9 (3) | N3—C4—N29—C30 | −12.1 (3) |
C6—C7—C8—N23 | 137.9 (2) | C5—C4—N29—C30 | 165.4 (2) |
C8—C7—N9—N10 | 3.9 (3) | N3—C4—N29—C34 | 127.5 (2) |
C6—C7—N9—N10 | −179.97 (17) | C5—C4—N29—C34 | −55.0 (3) |
C7—N9—N10—C11 | −171.47 (18) | C4—N29—C30—C31 | −163.4 (2) |
N9—N10—C11—C16 | 6.0 (3) | C34—N29—C30—C31 | 54.6 (3) |
N9—N10—C11—C12 | −175.82 (17) | N29—C30—C31—O32 | −57.8 (4) |
N10—C11—C12—C13 | −175.83 (19) | C30—C31—O32—C33 | 61.1 (4) |
C16—C11—C12—C13 | 2.4 (3) | C31—O32—C33—C34 | −59.9 (4) |
N10—C11—C12—N17 | 6.1 (3) | C4—N29—C34—C33 | 164.2 (2) |
C16—C11—C12—N17 | −175.6 (2) | C30—N29—C34—C33 | −54.2 (3) |
C11—C12—C13—C14 | −1.6 (3) | O32—C33—C34—N29 | 56.2 (3) |
N17—C12—C13—C14 | 176.6 (2) | N1—C5—N35—O37 | −11.9 (3) |
C12—C13—C14—C15 | −0.6 (3) | C4—C5—N35—O37 | −178.79 (19) |
C12—C13—C14—N20 | −179.67 (19) | N1—C5—N35—O36 | 166.79 (17) |
C13—C14—C15—C16 | 1.8 (3) | C4—C5—N35—O36 | −0.1 (3) |
N20—C14—C15—C16 | −179.17 (19) | C42—O38—C39—C40 | 29.8 (7) |
C14—C15—C16—C11 | −0.8 (3) | O38—C39—C40—C41 | −19.1 (9) |
N10—C11—C16—C15 | 177.07 (19) | C39—C40—C41—C42 | 2.1 (10) |
C12—C11—C16—C15 | −1.2 (3) | C39—O38—C42—C41 | −28.2 (7) |
C13—C12—N17—O19 | 3.6 (4) | C40—C41—C42—O38 | 15.9 (9) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N10—H10A···O18 | 1.00 (3) | 2.02 (3) | 2.629 (2) | 117.1 (19) |
N10—H10A···N23 | 1.00 (3) | 1.96 (3) | 2.763 (2) | 136 (2) |
C2—H2A···O36i | 0.91 (3) | 2.37 (3) | 3.195 (3) | 151 (2) |
C15—H15A···O38ii | 0.93 (2) | 2.35 (3) | 3.230 (4) | 159 (2) |
C24—H24A···O37 | 0.97 (3) | 2.51 (3) | 3.284 (3) | 136.8 (19) |
C34—H34A···O36 | 0.97 (3) | 2.31 (3) | 2.973 (3) | 125.1 (19) |
C34—H34B···O19iii | 1.02 (3) | 2.58 (3) | 3.444 (3) | 142 (2) |
C6—H6A···O37 | 0.97 (3) | 2.38 (3) | 2.771 (3) | 103.2 (19) |
C16—H16A···N9 | 0.93 (2) | 2.36 (2) | 2.711 (2) | 102.0 (15) |
Symmetry codes: (i) x−1, y, z; (ii) x, y, z+1; (iii) −x+1, −y+1, −z+2. |
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