Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806029515/cs2018sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806029515/cs2018Isup2.hkl |
CCDC reference: 620768
Data collection: CrysAlis CCD (Oxford Diffraction, 2001); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 and enCIFer (Allen et al., 2004).
C8H11N3O3 | Dx = 1.378 Mg m−3 |
Mr = 197.20 | Melting point: 383 K K |
Tetragonal, P43 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 4cw | Cell parameters from 32167 reflections |
a = 16.887 (6) Å | θ = 3.1–35.0° |
c = 13.332 (5) Å | µ = 0.11 mm−1 |
V = 3802 (2) Å3 | T = 100 K |
Z = 16 | Prism, colourless |
F(000) = 1664 | 0.63 × 0.52 × 0.35 mm |
Kuma KM4 CCD area-detector diffractometer | 7874 independent reflections |
Radiation source: fine-focus sealed tube | 6125 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
ω scans | θmax = 37.5°, θmin = 3.1° |
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2001) | h = −26→23 |
Tmin = 0.929, Tmax = 0.963 | k = −21→27 |
37699 measured reflections | l = −17→22 |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.115 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.071P)2] where P = (Fo2 + 2Fc2)/3 |
7874 reflections | (Δ/σ)max < 0.001 |
513 parameters | Δρmax = 0.48 e Å−3 |
1 restraint | Δρmin = −0.36 e Å−3 |
Experimental. crystallization from DMF |
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. The absolute structure Flack parameter is inconclusive for CHNO compound. Absolute structure not discussed. |
x | y | z | Uiso*/Ueq | ||
N1A | 0.70036 (8) | 0.52791 (8) | −0.02037 (10) | 0.0147 (3) | |
N2A | 0.78154 (8) | 0.51636 (8) | −0.03002 (10) | 0.0155 (3) | |
C3A | 0.78984 (10) | 0.43787 (10) | −0.03228 (11) | 0.0152 (3) | |
N3A | 0.86082 (8) | 0.40294 (9) | −0.04468 (11) | 0.0194 (3) | |
H3A1 | 0.9037 | 0.4321 | −0.0516 | 0.023* | |
H3A2 | 0.8644 | 0.3510 | −0.0458 | 0.023* | |
C4A | 0.71427 (10) | 0.39882 (10) | −0.02344 (12) | 0.0148 (3) | |
C5A | 0.65956 (10) | 0.45906 (10) | −0.01628 (12) | 0.0157 (3) | |
H5A | 0.6038 | 0.4533 | −0.0097 | 0.019* | |
C1A | 0.66713 (10) | 0.60456 (10) | −0.01792 (11) | 0.0162 (3) | |
O1A | 0.59496 (7) | 0.61043 (8) | −0.01590 (10) | 0.0226 (3) | |
C2A | 0.72431 (10) | 0.67128 (10) | −0.01700 (14) | 0.0200 (3) | |
H2A1 | 0.7552 | 0.6708 | −0.0792 | 0.030* | |
H2A2 | 0.7600 | 0.6657 | 0.0405 | 0.030* | |
H2A3 | 0.6954 | 0.7214 | −0.0117 | 0.030* | |
C6A | 0.69975 (10) | 0.31378 (10) | −0.02540 (12) | 0.0160 (3) | |
O6A | 0.75112 (8) | 0.26354 (7) | −0.02915 (11) | 0.0243 (3) | |
O7A | 0.62150 (7) | 0.29713 (7) | −0.02309 (9) | 0.0192 (2) | |
C7A | 0.60000 (11) | 0.21360 (10) | −0.02919 (14) | 0.0207 (3) | |
H7A1 | 0.6149 | 0.1858 | 0.0334 | 0.025* | |
H7A2 | 0.6276 | 0.1880 | −0.0861 | 0.025* | |
C8A | 0.51138 (11) | 0.21063 (12) | −0.04439 (14) | 0.0256 (4) | |
H8A1 | 0.4943 | 0.1553 | −0.0497 | 0.038* | |
H8A2 | 0.4975 | 0.2389 | −0.1061 | 0.038* | |
H8A3 | 0.4849 | 0.2357 | 0.0128 | 0.038* | |
N1B | 0.62325 (8) | −0.07923 (8) | −0.05593 (10) | 0.0146 (3) | |
N2B | 0.61118 (8) | −0.15995 (8) | −0.04260 (10) | 0.0158 (3) | |
C3B | 0.53251 (10) | −0.16743 (10) | −0.04173 (11) | 0.0153 (3) | |
N3B | 0.49696 (9) | −0.23804 (9) | −0.02556 (12) | 0.0209 (3) | |
H3B1 | 0.5258 | −0.2807 | −0.0152 | 0.025* | |
H3B2 | 0.4450 | −0.2414 | −0.0254 | 0.025* | |
C4B | 0.49370 (9) | −0.09188 (9) | −0.05555 (11) | 0.0147 (3) | |
C5B | 0.55395 (9) | −0.03839 (9) | −0.06403 (12) | 0.0154 (3) | |
H5B | 0.5486 | 0.0171 | −0.0738 | 0.018* | |
C1B | 0.69976 (9) | −0.04680 (10) | −0.05951 (12) | 0.0154 (3) | |
O1B | 0.70693 (7) | 0.02492 (7) | −0.06251 (9) | 0.0200 (2) | |
C2B | 0.76622 (10) | −0.10523 (10) | −0.05829 (13) | 0.0194 (3) | |
H2B1 | 0.7607 | −0.1415 | −0.1152 | 0.029* | |
H2B2 | 0.7647 | −0.1354 | 0.0045 | 0.029* | |
H2B3 | 0.8168 | −0.0771 | −0.0634 | 0.029* | |
C6B | 0.40835 (10) | −0.07816 (9) | −0.05750 (11) | 0.0154 (3) | |
O6B | 0.35887 (7) | −0.13051 (7) | −0.05231 (10) | 0.0225 (3) | |
O7B | 0.39068 (7) | −0.00061 (7) | −0.06476 (9) | 0.0191 (2) | |
C7B | 0.30717 (10) | 0.02022 (10) | −0.05846 (14) | 0.0210 (3) | |
H7B1 | 0.2818 | −0.0080 | −0.0019 | 0.025* | |
H7B2 | 0.2795 | 0.0055 | −0.1212 | 0.025* | |
C8B | 0.30300 (11) | 0.10842 (11) | −0.04233 (14) | 0.0244 (4) | |
H8B1 | 0.2475 | 0.1248 | −0.0369 | 0.037* | |
H8B2 | 0.3278 | 0.1356 | −0.0992 | 0.037* | |
H8B3 | 0.3310 | 0.1223 | 0.0196 | 0.037* | |
N1C | 0.01782 (8) | −0.00079 (9) | −0.05932 (11) | 0.0165 (3) | |
N2C | −0.06377 (8) | 0.01086 (8) | −0.05705 (11) | 0.0170 (3) | |
C3C | −0.07160 (10) | 0.08937 (10) | −0.05517 (12) | 0.0164 (3) | |
N3C | −0.14403 (9) | 0.12397 (9) | −0.05203 (14) | 0.0260 (3) | |
H3C1 | −0.1870 | 0.0945 | −0.0512 | 0.031* | |
H3C2 | −0.1481 | 0.1759 | −0.0508 | 0.031* | |
C4C | 0.00407 (10) | 0.12862 (10) | −0.05552 (12) | 0.0157 (3) | |
C5C | 0.05886 (10) | 0.06857 (10) | −0.05807 (13) | 0.0166 (3) | |
H5C | 0.1148 | 0.0743 | −0.0588 | 0.020* | |
C1C | 0.05042 (10) | −0.07720 (10) | −0.06280 (13) | 0.0178 (3) | |
O1C | 0.12252 (7) | −0.08368 (7) | −0.06662 (11) | 0.0245 (3) | |
C2C | −0.00724 (10) | −0.14406 (10) | −0.06131 (14) | 0.0208 (3) | |
H2C1 | −0.0426 | −0.1399 | −0.1193 | 0.031* | |
H2C2 | −0.0385 | −0.1418 | 0.0006 | 0.031* | |
H2C3 | 0.0215 | −0.1944 | −0.0642 | 0.031* | |
C6C | 0.01798 (10) | 0.21369 (10) | −0.05072 (11) | 0.0159 (3) | |
O6C | −0.03495 (8) | 0.26289 (7) | −0.04565 (10) | 0.0220 (3) | |
O7C | 0.09531 (7) | 0.23157 (7) | −0.05256 (10) | 0.0194 (2) | |
C7C | 0.11517 (10) | 0.31519 (10) | −0.04406 (13) | 0.0201 (3) | |
H7C1 | 0.0948 | 0.3372 | 0.0198 | 0.024* | |
H7C2 | 0.0919 | 0.3455 | −0.1004 | 0.024* | |
C8C | 0.20495 (11) | 0.31965 (11) | −0.04708 (16) | 0.0273 (4) | |
H8C1 | 0.2217 | 0.3749 | −0.0396 | 0.041* | |
H8C2 | 0.2240 | 0.2990 | −0.1114 | 0.041* | |
H8C3 | 0.2270 | 0.2880 | 0.0078 | 0.041* | |
N1D | 0.09337 (8) | 0.60341 (8) | −0.05500 (10) | 0.0153 (2) | |
N2D | 0.10333 (8) | 0.68533 (8) | −0.05801 (11) | 0.0164 (3) | |
C3D | 0.18154 (10) | 0.69497 (9) | −0.05153 (11) | 0.0147 (3) | |
N3D | 0.21495 (9) | 0.76747 (9) | −0.05148 (13) | 0.0230 (3) | |
H3D1 | 0.1850 | 0.8100 | −0.0558 | 0.028* | |
H3D2 | 0.2667 | 0.7723 | −0.0471 | 0.028* | |
C4D | 0.22180 (10) | 0.61992 (10) | −0.04407 (11) | 0.0146 (3) | |
C5D | 0.16309 (10) | 0.56408 (10) | −0.04728 (12) | 0.0152 (3) | |
H5D | 0.1699 | 0.5083 | −0.0446 | 0.018* | |
C1D | 0.01774 (9) | 0.56863 (10) | −0.05765 (12) | 0.0166 (3) | |
O1D | 0.01262 (8) | 0.49680 (8) | −0.05167 (10) | 0.0245 (3) | |
C2D | −0.05075 (10) | 0.62425 (11) | −0.06884 (13) | 0.0204 (3) | |
H2D1 | −0.0467 | 0.6664 | −0.0185 | 0.031* | |
H2D3 | −0.1004 | 0.5952 | −0.0592 | 0.031* | |
H2D2 | −0.0500 | 0.6476 | −0.1361 | 0.031* | |
C6D | 0.30720 (10) | 0.60728 (10) | −0.03765 (11) | 0.0150 (3) | |
O6D | 0.35621 (7) | 0.65981 (7) | −0.03678 (10) | 0.0216 (3) | |
O7D | 0.32498 (7) | 0.52980 (7) | −0.03240 (9) | 0.0173 (2) | |
C7D | 0.40862 (10) | 0.50955 (10) | −0.03342 (13) | 0.0189 (3) | |
H7D1 | 0.4366 | 0.5361 | 0.0224 | 0.023* | |
H7D2 | 0.4333 | 0.5261 | −0.0975 | 0.023* | |
C8D | 0.41276 (12) | 0.42080 (11) | −0.02165 (16) | 0.0271 (4) | |
H8D1 | 0.4681 | 0.4036 | −0.0254 | 0.041* | |
H8D2 | 0.3824 | 0.3955 | −0.0754 | 0.041* | |
H8D3 | 0.3905 | 0.4057 | 0.0435 | 0.041* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0118 (7) | 0.0121 (7) | 0.0203 (5) | 0.0002 (5) | 0.0006 (5) | 0.0012 (5) |
N2A | 0.0112 (7) | 0.0148 (7) | 0.0204 (6) | 0.0003 (5) | 0.0008 (5) | 0.0008 (5) |
C3A | 0.0138 (8) | 0.0158 (8) | 0.0160 (6) | 0.0015 (6) | 0.0000 (5) | 0.0000 (5) |
N3A | 0.0137 (7) | 0.0138 (7) | 0.0308 (7) | 0.0018 (5) | 0.0033 (5) | −0.0015 (6) |
C4A | 0.0135 (8) | 0.0130 (8) | 0.0178 (6) | −0.0019 (6) | −0.0007 (5) | 0.0001 (5) |
C5A | 0.0125 (8) | 0.0143 (8) | 0.0204 (6) | −0.0020 (6) | 0.0002 (6) | 0.0008 (6) |
C1A | 0.0168 (8) | 0.0138 (8) | 0.0180 (6) | 0.0020 (6) | 0.0005 (6) | 0.0006 (5) |
O1A | 0.0165 (6) | 0.0188 (7) | 0.0324 (6) | 0.0025 (5) | 0.0008 (5) | 0.0010 (5) |
C2A | 0.0195 (9) | 0.0132 (8) | 0.0272 (7) | −0.0002 (6) | 0.0028 (6) | 0.0002 (6) |
C6A | 0.0149 (8) | 0.0143 (8) | 0.0189 (6) | −0.0024 (6) | −0.0006 (6) | 0.0001 (5) |
O6A | 0.0191 (7) | 0.0153 (6) | 0.0385 (7) | 0.0042 (5) | −0.0002 (5) | −0.0003 (5) |
O7A | 0.0158 (6) | 0.0126 (6) | 0.0291 (6) | −0.0026 (4) | −0.0005 (5) | −0.0002 (5) |
C7A | 0.0238 (9) | 0.0091 (8) | 0.0293 (8) | −0.0047 (6) | −0.0023 (7) | 0.0001 (6) |
C8A | 0.0251 (10) | 0.0232 (10) | 0.0284 (8) | −0.0065 (8) | −0.0041 (7) | −0.0006 (7) |
N1B | 0.0131 (6) | 0.0106 (6) | 0.0201 (5) | −0.0003 (5) | 0.0004 (5) | 0.0002 (5) |
N2B | 0.0145 (7) | 0.0115 (6) | 0.0214 (6) | −0.0019 (5) | −0.0008 (5) | 0.0021 (5) |
C3B | 0.0151 (8) | 0.0148 (8) | 0.0160 (6) | −0.0014 (6) | 0.0003 (5) | 0.0014 (5) |
N3B | 0.0151 (7) | 0.0144 (7) | 0.0333 (7) | −0.0019 (6) | −0.0019 (6) | 0.0044 (6) |
C4B | 0.0135 (8) | 0.0138 (8) | 0.0167 (6) | −0.0001 (5) | −0.0005 (5) | −0.0002 (5) |
C5B | 0.0149 (8) | 0.0132 (7) | 0.0180 (6) | 0.0015 (6) | −0.0002 (6) | 0.0004 (5) |
C1B | 0.0122 (7) | 0.0162 (8) | 0.0179 (6) | −0.0022 (6) | 0.0004 (5) | −0.0001 (6) |
O1B | 0.0167 (6) | 0.0147 (6) | 0.0286 (6) | −0.0033 (5) | 0.0003 (5) | 0.0007 (5) |
C2B | 0.0128 (8) | 0.0182 (8) | 0.0271 (7) | 0.0002 (6) | 0.0019 (6) | 0.0009 (6) |
C6B | 0.0146 (8) | 0.0152 (8) | 0.0165 (6) | 0.0012 (6) | −0.0003 (6) | 0.0004 (6) |
O6B | 0.0150 (6) | 0.0182 (6) | 0.0344 (6) | −0.0041 (5) | 0.0007 (5) | −0.0007 (5) |
O7B | 0.0128 (6) | 0.0154 (6) | 0.0291 (6) | 0.0020 (4) | −0.0004 (5) | 0.0018 (5) |
C7B | 0.0122 (8) | 0.0224 (9) | 0.0283 (7) | 0.0042 (6) | −0.0001 (6) | −0.0012 (7) |
C8B | 0.0210 (10) | 0.0227 (10) | 0.0296 (8) | 0.0050 (7) | −0.0020 (7) | −0.0019 (7) |
N1C | 0.0107 (7) | 0.0146 (6) | 0.0242 (6) | 0.0007 (5) | 0.0001 (5) | 0.0008 (5) |
N2C | 0.0105 (6) | 0.0148 (7) | 0.0255 (6) | 0.0021 (5) | 0.0008 (5) | 0.0003 (5) |
C3C | 0.0147 (8) | 0.0149 (8) | 0.0195 (6) | 0.0005 (6) | −0.0012 (6) | 0.0001 (6) |
N3C | 0.0149 (8) | 0.0158 (7) | 0.0473 (9) | 0.0018 (6) | −0.0011 (7) | −0.0028 (7) |
C4C | 0.0139 (8) | 0.0160 (8) | 0.0172 (6) | −0.0017 (6) | −0.0008 (6) | −0.0009 (6) |
C5C | 0.0136 (8) | 0.0149 (8) | 0.0212 (6) | −0.0021 (6) | −0.0002 (6) | 0.0000 (6) |
C1C | 0.0168 (8) | 0.0144 (8) | 0.0220 (7) | 0.0022 (6) | 0.0012 (6) | 0.0006 (6) |
O1C | 0.0159 (6) | 0.0188 (6) | 0.0387 (7) | 0.0045 (5) | 0.0021 (5) | 0.0004 (5) |
C2C | 0.0178 (8) | 0.0139 (8) | 0.0307 (8) | 0.0022 (6) | 0.0033 (7) | −0.0001 (7) |
C6C | 0.0147 (8) | 0.0155 (8) | 0.0176 (6) | −0.0021 (6) | 0.0002 (5) | 0.0004 (5) |
O6C | 0.0200 (6) | 0.0135 (6) | 0.0325 (6) | 0.0026 (5) | −0.0013 (5) | −0.0012 (5) |
O7C | 0.0156 (6) | 0.0128 (6) | 0.0299 (6) | −0.0023 (4) | 0.0007 (5) | −0.0012 (5) |
C7C | 0.0211 (9) | 0.0124 (8) | 0.0269 (8) | −0.0048 (6) | 0.0009 (6) | −0.0003 (6) |
C8C | 0.0225 (10) | 0.0221 (10) | 0.0373 (10) | −0.0082 (7) | 0.0049 (8) | −0.0052 (8) |
N1D | 0.0131 (7) | 0.0133 (6) | 0.0196 (6) | −0.0012 (5) | 0.0002 (5) | 0.0022 (5) |
N2D | 0.0153 (7) | 0.0124 (7) | 0.0216 (6) | −0.0012 (5) | −0.0001 (5) | 0.0013 (5) |
C3D | 0.0135 (8) | 0.0146 (8) | 0.0160 (6) | −0.0007 (6) | 0.0002 (5) | 0.0002 (5) |
N3D | 0.0143 (7) | 0.0122 (7) | 0.0425 (9) | −0.0010 (5) | 0.0012 (6) | −0.0022 (6) |
C4D | 0.0125 (8) | 0.0149 (8) | 0.0164 (6) | 0.0014 (6) | 0.0000 (5) | 0.0003 (5) |
C5D | 0.0122 (8) | 0.0142 (8) | 0.0191 (6) | 0.0011 (6) | −0.0011 (5) | 0.0014 (5) |
C1D | 0.0124 (7) | 0.0190 (8) | 0.0185 (6) | −0.0021 (6) | 0.0001 (6) | 0.0024 (6) |
O1D | 0.0201 (7) | 0.0177 (6) | 0.0357 (7) | −0.0045 (5) | 0.0022 (6) | 0.0024 (5) |
C2D | 0.0129 (8) | 0.0211 (9) | 0.0273 (8) | −0.0003 (6) | −0.0004 (6) | 0.0035 (6) |
C6D | 0.0132 (8) | 0.0150 (8) | 0.0167 (6) | 0.0014 (6) | −0.0008 (5) | −0.0006 (5) |
O6D | 0.0158 (6) | 0.0166 (6) | 0.0324 (6) | −0.0018 (5) | −0.0019 (5) | −0.0009 (5) |
O7D | 0.0116 (6) | 0.0151 (6) | 0.0253 (5) | 0.0028 (4) | −0.0011 (4) | 0.0005 (4) |
C7D | 0.0109 (8) | 0.0214 (9) | 0.0243 (7) | 0.0043 (6) | −0.0016 (6) | −0.0016 (6) |
C8D | 0.0214 (10) | 0.0223 (10) | 0.0377 (9) | 0.0068 (7) | 0.0032 (8) | 0.0079 (8) |
N1A—C5A | 1.353 (2) | N1C—C5C | 1.361 (2) |
N1A—N2A | 1.391 (2) | N1C—N2C | 1.392 (2) |
N1A—C1A | 1.411 (2) | N1C—C1C | 1.404 (2) |
N2A—C3A | 1.333 (2) | N2C—C3C | 1.332 (2) |
C3A—N3A | 1.346 (2) | C3C—N3C | 1.356 (2) |
C3A—C4A | 1.441 (2) | C3C—C4C | 1.440 (2) |
N3A—H3A1 | 0.88 | N3C—H3C1 | 0.8800 |
N3A—H3A2 | 0.88 | N3C—H3C2 | 0.8800 |
C4A—C5A | 1.377 (2) | C4C—C5C | 1.373 (2) |
C4A—C6A | 1.457 (2) | C4C—C6C | 1.457 (2) |
C5A—H5A | 0.95 | C5C—H5C | 0.9500 |
C1A—O1A | 1.223 (2) | C1C—O1C | 1.224 (2) |
C1A—C2A | 1.484 (2) | C1C—C2C | 1.491 (2) |
C2A—H2A1 | 0.98 | C2C—H2C1 | 0.9800 |
C2A—H2A2 | 0.98 | C2C—H2C2 | 0.9800 |
C2A—H2A3 | 0.98 | C2C—H2C3 | 0.9800 |
C6A—O6A | 1.214 (2) | C6C—O6C | 1.222 (2) |
C6A—O7A | 1.351 (2) | C6C—O7C | 1.341 (2) |
O7A—C7A | 1.459 (2) | O7C—C7C | 1.456 (2) |
C7A—C8A | 1.511 (3) | C7C—C8C | 1.518 (3) |
C7A—H7A1 | 0.9900 | C7C—H7C1 | 0.9900 |
C7A—H7A2 | 0.9900 | C7C—H7C2 | 0.9900 |
C8A—H8A1 | 0.9800 | C8C—H8C1 | 0.9800 |
C8A—H8A2 | 0.9800 | C8C—H8C2 | 0.9800 |
C8A—H8A3 | 0.9800 | C8C—H8C3 | 0.9800 |
N1B—C5B | 1.363 (2) | N1D—C5D | 1.356 (2) |
N1B—N2B | 1.390 (2) | N1D—N2D | 1.394 (2) |
N1B—C1B | 1.404 (2) | N1D—C1D | 1.406 (2) |
N2B—C3B | 1.335 (2) | N2D—C3D | 1.333 (2) |
C3B—N3B | 1.352 (2) | C3D—N3D | 1.348 (2) |
C3B—C4B | 1.446 (2) | C3D—C4D | 1.442 (2) |
N3B—H3B1 | 0.8800 | N3D—H3D1 | 0.8800 |
N3B—H3B2 | 0.8800 | N3D—H3D2 | 0.8800 |
C4B—C5B | 1.365 (2) | C4D—C5D | 1.369 (2) |
C4B—C6B | 1.460 (2) | C4D—C6D | 1.460 (2) |
C5B—H5B | 0.9500 | C5D—H5D | 0.9500 |
C1B—O1B | 1.218 (2) | C1D—O1D | 1.219 (2) |
C1B—C2B | 1.494 (2) | C1D—C2D | 1.497 (2) |
C2B—H2B1 | 0.9800 | C2D—H2D1 | 0.9800 |
C2B—H2B2 | 0.9800 | C2D—H2D3 | 0.9800 |
C2B—H2B3 | 0.9800 | C2D—H2D2 | 0.9800 |
C6B—O6B | 1.219 (2) | C6D—O6D | 1.213 (2) |
C6B—O7B | 1.347 (2) | C6D—O7D | 1.344 (2) |
O7B—C7B | 1.456 (2) | O7D—C7D | 1.453 (2) |
C7B—C8B | 1.507 (2) | C7D—C8D | 1.508 (2) |
C7B—H7B1 | 0.9900 | C7D—H7D1 | 0.9900 |
C7B—H7B2 | 0.9900 | C7D—H7D2 | 0.9900 |
C8B—H8B1 | 0.9800 | C8D—H8D1 | 0.9800 |
C8B—H8B2 | 0.9800 | C8D—H8D2 | 0.9800 |
C8B—H8B3 | 0.9800 | C8D—H8D3 | 0.9800 |
C5A—N1A—N2A | 112.66 (13) | C5C—N1C—N2C | 112.45 (13) |
C5A—N1A—C1A | 125.80 (14) | C5C—N1C—C1C | 126.29 (14) |
N2A—N1A—C1A | 121.52 (13) | N2C—N1C—C1C | 121.26 (13) |
C3A—N2A—N1A | 104.19 (13) | C3C—N2C—N1C | 103.85 (13) |
N2A—C3A—N3A | 122.13 (16) | N2C—C3C—N3C | 121.25 (15) |
N2A—C3A—C4A | 111.10 (14) | N2C—C3C—C4C | 111.71 (14) |
N3A—C3A—C4A | 126.73 (16) | N3C—C3C—C4C | 127.04 (16) |
C3A—N3A—H3A1 | 120.0 | C3C—N3C—H3C1 | 120.0 |
C3A—N3A—H3A2 | 120.0 | C3C—N3C—H3C2 | 120.0 |
H3A1—N3A—H3A2 | 120.0 | H3C1—N3C—H3C2 | 120.0 |
C5A—C4A—C3A | 105.17 (14) | C5C—C4C—C3C | 104.96 (14) |
C5A—C4A—C6A | 128.04 (15) | C5C—C4C—C6C | 128.36 (15) |
C3A—C4A—C6A | 126.76 (15) | C3C—C4C—C6C | 126.65 (15) |
N1A—C5A—C4A | 106.88 (14) | N1C—C5C—C4C | 107.03 (14) |
N1A—C5A—H5A | 126.6 | N1C—C5C—H5C | 126.5 |
C4A—C5A—H5A | 126.6 | C4C—C5C—H5C | 126.5 |
O1A—C1A—N1A | 118.11 (15) | O1C—C1C—N1C | 118.29 (15) |
O1A—C1A—C2A | 125.92 (15) | O1C—C1C—C2C | 125.63 (15) |
N1A—C1A—C2A | 115.97 (14) | N1C—C1C—C2C | 116.08 (14) |
C1A—C2A—H2A1 | 109.5 | C1C—C2C—H2C1 | 109.5 |
C1A—C2A—H2A2 | 109.5 | C1C—C2C—H2C2 | 109.5 |
H2A1—C2A—H2A2 | 109.5 | H2C1—C2C—H2C2 | 109.5 |
C1A—C2A—H2A3 | 109.5 | C1C—C2C—H2C3 | 109.5 |
H2A1—C2A—H2A3 | 109.5 | H2C1—C2C—H2C3 | 109.5 |
H2A2—C2A—H2A3 | 109.5 | H2C2—C2C—H2C3 | 109.5 |
O6A—C6A—O7A | 123.64 (15) | O6C—C6C—O7C | 124.08 (15) |
O6A—C6A—C4A | 124.69 (15) | O6C—C6C—C4C | 123.69 (15) |
O7A—C6A—C4A | 111.67 (14) | O7C—C6C—C4C | 112.23 (14) |
C6A—O7A—C7A | 116.32 (13) | C6C—O7C—C7C | 116.20 (13) |
O7A—C7A—C8A | 106.63 (15) | O7C—C7C—C8C | 106.02 (14) |
O7A—C7A—H7A1 | 110.4 | O7C—C7C—H7C1 | 110.5 |
C8A—C7A—H7A1 | 110.4 | C8C—C7C—H7C1 | 110.5 |
O7A—C7A—H7A2 | 110.4 | O7C—C7C—H7C2 | 110.5 |
C8A—C7A—H7A2 | 110.4 | C8C—C7C—H7C2 | 110.5 |
H7A1—C7A—H7A2 | 108.6 | H7C1—C7C—H7C2 | 108.7 |
C7A—C8A—H8A1 | 109.5 | C7C—C8C—H8C1 | 109.5 |
C7A—C8A—H8A2 | 109.5 | C7C—C8C—H8C2 | 109.5 |
H8A1—C8A—H8A2 | 109.5 | H8C1—C8C—H8C2 | 109.5 |
C7A—C8A—H8A3 | 109.5 | C7C—C8C—H8C3 | 109.5 |
H8A1—C8A—H8A3 | 109.5 | H8C1—C8C—H8C3 | 109.5 |
H8A2—C8A—H8A3 | 109.5 | H8C2—C8C—H8C3 | 109.5 |
C5B—N1B—N2B | 112.38 (13) | C5D—N1D—N2D | 112.55 (13) |
C5B—N1B—C1B | 126.16 (14) | C5D—N1D—C1D | 125.88 (14) |
N2B—N1B—C1B | 121.46 (13) | N2D—N1D—C1D | 121.55 (13) |
C3B—N2B—N1B | 103.88 (13) | C3D—N2D—N1D | 103.81 (13) |
N2B—C3B—N3B | 121.78 (15) | N2D—C3D—N3D | 121.69 (15) |
N2B—C3B—C4B | 111.50 (14) | N2D—C3D—C4D | 111.36 (14) |
N3B—C3B—C4B | 126.67 (15) | N3D—C3D—C4D | 126.94 (15) |
C3B—N3B—H3B1 | 120.0 | C3D—N3D—H3D1 | 120.0 |
C3B—N3B—H3B2 | 120.0 | C3D—N3D—H3D2 | 120.0 |
H3B1—N3B—H3B2 | 120.0 | H3D1—N3D—H3D2 | 120.0 |
C5B—C4B—C3B | 104.87 (14) | C5D—C4D—C3D | 105.18 (14) |
C5B—C4B—C6B | 129.00 (15) | C5D—C4D—C6D | 128.05 (15) |
C3B—C4B—C6B | 126.12 (14) | C3D—C4D—C6D | 126.75 (15) |
N1B—C5B—C4B | 107.37 (14) | N1D—C5D—C4D | 107.09 (14) |
N1B—C5B—H5B | 126.3 | N1D—C5D—H5D | 126.5 |
C4B—C5B—H5B | 126.3 | C4D—C5D—H5D | 126.5 |
O1B—C1B—N1B | 118.72 (15) | O1D—C1D—N1D | 118.58 (15) |
O1B—C1B—C2B | 125.61 (15) | O1D—C1D—C2D | 125.17 (15) |
N1B—C1B—C2B | 115.67 (14) | N1D—C1D—C2D | 116.24 (14) |
C1B—C2B—H2B1 | 109.5 | C1D—C2D—H2D1 | 109.5 |
C1B—C2B—H2B2 | 109.5 | C1D—C2D—H2D3 | 109.5 |
H2B1—C2B—H2B2 | 109.5 | H2D1—C2D—H2D3 | 109.5 |
C1B—C2B—H2B3 | 109.5 | C1D—C2D—H2D2 | 109.5 |
H2B1—C2B—H2B3 | 109.5 | H2D1—C2D—H2D2 | 109.5 |
H2B2—C2B—H2B3 | 109.5 | H2D3—C2D—H2D2 | 109.5 |
O6B—C6B—O7B | 123.90 (15) | O6D—C6D—O7D | 123.96 (15) |
O6B—C6B—C4B | 124.12 (15) | O6D—C6D—C4D | 124.57 (15) |
O7B—C6B—C4B | 111.98 (14) | O7D—C6D—C4D | 111.47 (14) |
C6B—O7B—C7B | 116.45 (13) | C6D—O7D—C7D | 116.47 (13) |
O7B—C7B—C8B | 107.00 (14) | O7D—C7D—C8D | 106.13 (14) |
O7B—C7B—H7B1 | 110.3 | O7D—C7D—H7D1 | 110.5 |
C8B—C7B—H7B1 | 110.3 | C8D—C7D—H7D1 | 110.5 |
O7B—C7B—H7B2 | 110.3 | O7D—C7D—H7D2 | 110.5 |
C8B—C7B—H7B2 | 110.3 | C8D—C7D—H7D2 | 110.5 |
H7B1—C7B—H7B2 | 108.6 | H7D1—C7D—H7D2 | 108.7 |
C7B—C8B—H8B1 | 109.5 | C7D—C8D—H8D1 | 109.5 |
C7B—C8B—H8B2 | 109.5 | C7D—C8D—H8D2 | 109.5 |
H8B1—C8B—H8B2 | 109.5 | H8D1—C8D—H8D2 | 109.5 |
C7B—C8B—H8B3 | 109.5 | C7D—C8D—H8D3 | 109.5 |
H8B1—C8B—H8B3 | 109.5 | H8D1—C8D—H8D3 | 109.5 |
H8B2—C8B—H8B3 | 109.5 | H8D2—C8D—H8D3 | 109.5 |
C5A—N1A—N2A—C3A | 0.28 (17) | C5C—N1C—N2C—C3C | 0.47 (19) |
C1A—N1A—N2A—C3A | −178.30 (13) | C1C—N1C—N2C—C3C | −179.34 (14) |
N1A—N2A—C3A—N3A | 177.63 (15) | N1C—N2C—C3C—N3C | −179.60 (16) |
N1A—N2A—C3A—C4A | −0.38 (16) | N1C—N2C—C3C—C4C | −0.39 (18) |
N2A—C3A—C4A—C5A | 0.35 (18) | N2C—C3C—C4C—C5C | 0.19 (19) |
N3A—C3A—C4A—C5A | −177.54 (16) | N3C—C3C—C4C—C5C | 179.34 (18) |
N2A—C3A—C4A—C6A | 178.40 (15) | N2C—C3C—C4C—C6C | −177.95 (15) |
N3A—C3A—C4A—C6A | 0.5 (3) | N3C—C3C—C4C—C6C | 1.2 (3) |
N2A—N1A—C5A—C4A | −0.07 (18) | N2C—N1C—C5C—C4C | −0.36 (19) |
C1A—N1A—C5A—C4A | 178.45 (14) | C1C—N1C—C5C—C4C | 179.43 (15) |
C3A—C4A—C5A—N1A | −0.16 (17) | C3C—C4C—C5C—N1C | 0.11 (17) |
C6A—C4A—C5A—N1A | −178.17 (15) | C6C—C4C—C5C—N1C | 178.21 (15) |
C5A—N1A—C1A—O1A | −3.1 (2) | C5C—N1C—C1C—O1C | −1.2 (2) |
N2A—N1A—C1A—O1A | 175.31 (14) | N2C—N1C—C1C—O1C | 178.62 (15) |
C5A—N1A—C1A—C2A | 176.31 (15) | C5C—N1C—C1C—C2C | 178.74 (16) |
N2A—N1A—C1A—C2A | −5.3 (2) | N2C—N1C—C1C—C2C | −1.5 (2) |
C5A—C4A—C6A—O6A | −177.91 (17) | C5C—C4C—C6C—O6C | −177.69 (17) |
C3A—C4A—C6A—O6A | 4.5 (3) | C3C—C4C—C6C—O6C | 0.0 (3) |
C5A—C4A—C6A—O7A | 2.4 (2) | C5C—C4C—C6C—O7C | 2.3 (2) |
C3A—C4A—C6A—O7A | −175.19 (14) | C3C—C4C—C6C—O7C | −179.94 (14) |
O6A—C6A—O7A—C7A | −2.3 (2) | O6C—C6C—O7C—C7C | 2.4 (2) |
C4A—C6A—O7A—C7A | 177.41 (13) | C4C—C6C—O7C—C7C | −177.66 (13) |
C6A—O7A—C7A—C8A | −169.86 (14) | C6C—O7C—C7C—C8C | 179.49 (14) |
C5B—N1B—N2B—C3B | −0.61 (17) | C5D—N1D—N2D—C3D | −0.20 (17) |
C1B—N1B—N2B—C3B | 179.09 (13) | C1D—N1D—N2D—C3D | 178.47 (13) |
N1B—N2B—C3B—N3B | −176.95 (14) | N1D—N2D—C3D—N3D | −179.65 (15) |
N1B—N2B—C3B—C4B | 0.63 (16) | N1D—N2D—C3D—C4D | −0.19 (17) |
N2B—C3B—C4B—C5B | −0.45 (17) | N2D—C3D—C4D—C5D | 0.49 (18) |
N3B—C3B—C4B—C5B | 176.99 (16) | N3D—C3D—C4D—C5D | 179.92 (16) |
N2B—C3B—C4B—C6B | −179.34 (14) | N2D—C3D—C4D—C6D | 178.79 (14) |
N3B—C3B—C4B—C6B | −1.9 (3) | N3D—C3D—C4D—C6D | −1.8 (3) |
N2B—N1B—C5B—C4B | 0.34 (18) | N2D—N1D—C5D—C4D | 0.52 (18) |
C1B—N1B—C5B—C4B | −179.34 (14) | C1D—N1D—C5D—C4D | −178.09 (14) |
C3B—C4B—C5B—N1B | 0.05 (17) | C3D—C4D—C5D—N1D | −0.58 (17) |
C6B—C4B—C5B—N1B | 178.90 (15) | C6D—C4D—C5D—N1D | −178.85 (14) |
C5B—N1B—C1B—O1B | 6.0 (2) | C5D—N1D—C1D—O1D | 0.7 (2) |
N2B—N1B—C1B—O1B | −173.65 (14) | N2D—N1D—C1D—O1D | −177.76 (14) |
C5B—N1B—C1B—C2B | −174.56 (15) | C5D—N1D—C1D—C2D | −178.67 (15) |
N2B—N1B—C1B—C2B | 5.8 (2) | N2D—N1D—C1D—C2D | 2.8 (2) |
C5B—C4B—C6B—O6B | 177.68 (16) | C5D—C4D—C6D—O6D | 178.70 (16) |
C3B—C4B—C6B—O6B | −3.7 (3) | C3D—C4D—C6D—O6D | 0.8 (2) |
C5B—C4B—C6B—O7B | −2.9 (2) | C5D—C4D—C6D—O7D | −1.5 (2) |
C3B—C4B—C6B—O7B | 175.70 (14) | C3D—C4D—C6D—O7D | −179.46 (14) |
O6B—C6B—O7B—C7B | 4.6 (2) | O6D—C6D—O7D—C7D | −4.8 (2) |
C4B—C6B—O7B—C7B | −174.80 (13) | C4D—C6D—O7D—C7D | 175.47 (13) |
C6B—O7B—C7B—C8B | 166.16 (13) | C6D—O7D—C7D—C8D | 177.23 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3A—H3A2···O6A | 0.88 | 2.43 | 3.003 (2) | 124 |
N3A—H3A2···O6Ci | 0.88 | 2.26 | 2.948 (2) | 135 |
N3A—H3A1···O1Di | 0.88 | 2.14 | 3.015 (2) | 173 |
N3B—H3B2···O6B | 0.88 | 2.40 | 2.977 (2) | 124 |
N3B—H3B2···O6Dii | 0.88 | 2.25 | 2.941 (2) | 136 |
N3B—H3B1···O1Aii | 0.88 | 2.18 | 3.050 (2) | 171 |
N3C—H3C2···O6C | 0.88 | 2.41 | 2.984 (2) | 123 |
N3C—H3C2···O6Aiii | 0.88 | 2.27 | 2.964 (2) | 135 |
N3C—H3C1···O1Biii | 0.88 | 2.15 | 3.025 (2) | 175 |
N3D—H3D2···O6D | 0.88 | 2.43 | 3.006 (2) | 123 |
N3D—H3D1···O1Civ | 0.88 | 2.09 | 2.966 (2) | 175 |
N3D—H3D2···O6Biv | 0.88 | 2.26 | 2.979 (2) | 139 |
Symmetry codes: (i) x+1, y, z; (ii) x, y−1, z; (iii) x−1, y, z; (iv) x, y+1, z. |