Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806002996/cv6640sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806002996/cv6640Isup2.hkl |
CCDC reference: 298423
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.
C10H9N7O3 | Z = 4 |
Mr = 275.24 | F(000) = 568 |
Triclinic, P1 | Dx = 1.487 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.7412 (19) Å | Cell parameters from 1528 reflections |
b = 10.530 (2) Å | θ = 2.4–22.4° |
c = 13.881 (3) Å | µ = 0.12 mm−1 |
α = 81.964 (3)° | T = 298 K |
β = 89.058 (3)° | Block, colourless |
γ = 76.467 (3)° | 0.40 × 0.38 × 0.28 mm |
V = 1229.8 (4) Å3 |
Bruker SMART CCD area-detector diffractometer | 4273 independent reflections |
Radiation source: fine-focus sealed tube | 3416 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.014 |
φ and ω scans | θmax = 25.0°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→9 |
Tmin = 0.955, Tmax = 0.968 | k = −12→8 |
6260 measured reflections | l = −16→16 |
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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.139 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0643P)2 + 0.1542P] where P = (Fo2 + 2Fc2)/3 |
4273 reflections | (Δ/σ)max < 0.001 |
361 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.37799 (19) | 0.44865 (16) | 0.84885 (13) | 0.0587 (5) | |
O2 | 0.1215 (2) | 0.85965 (16) | 0.87452 (14) | 0.0627 (5) | |
O3 | 0.6580 (2) | 0.74972 (19) | 0.89096 (15) | 0.0704 (5) | |
O4 | 0.30287 (19) | 0.27619 (15) | 0.56331 (12) | 0.0539 (4) | |
O5 | −0.0171 (2) | 0.64580 (16) | 0.63154 (15) | 0.0685 (5) | |
O6 | 0.1006 (2) | 0.28786 (17) | 0.86618 (13) | 0.0668 (5) | |
N1 | 0.5668 (3) | 0.4539 (2) | 0.66567 (16) | 0.0600 (6) | |
N2 | 0.7100 (3) | 0.1992 (2) | 0.85962 (16) | 0.0665 (6) | |
N3 | 0.5847 (3) | 0.2667 (2) | 0.89786 (16) | 0.0657 (6) | |
N4 | 0.5192 (2) | 0.36691 (18) | 0.83064 (15) | 0.0522 (5) | |
N5 | 0.2498 (2) | 0.65297 (19) | 0.86509 (15) | 0.0522 (5) | |
N6 | 0.3900 (2) | 0.81687 (19) | 0.87963 (13) | 0.0484 (5) | |
N7 | 0.5296 (2) | 0.5956 (2) | 0.87216 (15) | 0.0525 (5) | |
N8 | 0.1776 (2) | 0.0294 (2) | 0.57196 (16) | 0.0589 (6) | |
N9 | 0.5751 (2) | −0.0074 (2) | 0.64232 (16) | 0.0591 (6) | |
N10 | 0.5279 (2) | 0.1203 (2) | 0.62374 (16) | 0.0564 (6) | |
N11 | 0.3771 (2) | 0.14781 (18) | 0.59594 (14) | 0.0457 (5) | |
N12 | 0.1463 (2) | 0.46196 (18) | 0.59808 (15) | 0.0510 (5) | |
N13 | 0.0302 (2) | 0.47130 (18) | 0.75356 (16) | 0.0503 (5) | |
N14 | 0.2062 (2) | 0.27395 (17) | 0.71977 (14) | 0.0467 (5) | |
C1 | 0.7230 (3) | 0.2597 (2) | 0.76616 (18) | 0.0487 (6) | |
C2 | 0.8311 (3) | 0.2323 (3) | 0.6931 (2) | 0.0598 (7) | |
H2B | 0.9162 | 0.1595 | 0.7009 | 0.072* | |
C3 | 0.8043 (3) | 0.3188 (3) | 0.6094 (2) | 0.0637 (7) | |
H3B | 0.8744 | 0.3067 | 0.5585 | 0.076* | |
C4 | 0.6740 (3) | 0.4251 (3) | 0.5985 (2) | 0.0685 (8) | |
H4A | 0.6610 | 0.4804 | 0.5393 | 0.082* | |
C5 | 0.5993 (3) | 0.3682 (2) | 0.74659 (17) | 0.0440 (5) | |
C6 | 0.3898 (3) | 0.5737 (2) | 0.86318 (17) | 0.0472 (6) | |
C7 | 0.2598 (3) | 0.7752 (2) | 0.87333 (16) | 0.0477 (6) | |
C8 | 0.5198 (3) | 0.7221 (3) | 0.88086 (17) | 0.0499 (6) | |
C9 | 0.1225 (3) | 0.9943 (2) | 0.8837 (2) | 0.0758 (9) | |
H9B | 0.0162 | 1.0458 | 0.8839 | 0.114* | |
H9C | 0.1771 | 1.0300 | 0.8299 | 0.114* | |
H9D | 0.1748 | 0.9965 | 0.9435 | 0.114* | |
C10 | 0.6603 (4) | 0.8833 (3) | 0.9030 (3) | 0.0873 (10) | |
H10B | 0.7672 | 0.8901 | 0.9089 | 0.131* | |
H10C | 0.6043 | 0.9061 | 0.9605 | 0.131* | |
H10D | 0.6108 | 0.9426 | 0.8474 | 0.131* | |
C11 | 0.4507 (3) | −0.0615 (2) | 0.62583 (16) | 0.0435 (5) | |
C12 | 0.4345 (3) | −0.1907 (2) | 0.63291 (17) | 0.0552 (7) | |
H12B | 0.5175 | −0.2625 | 0.6526 | 0.066* | |
C13 | 0.2913 (3) | −0.2056 (3) | 0.60960 (19) | 0.0624 (7) | |
H13B | 0.2739 | −0.2900 | 0.6130 | 0.075* | |
C14 | 0.1685 (3) | −0.0958 (3) | 0.5803 (2) | 0.0685 (8) | |
H14B | 0.0720 | −0.1119 | 0.5654 | 0.082* | |
C15 | 0.3213 (3) | 0.0383 (2) | 0.59527 (15) | 0.0414 (5) | |
C16 | 0.2131 (3) | 0.3396 (2) | 0.63354 (17) | 0.0434 (5) | |
C17 | 0.0543 (3) | 0.5229 (2) | 0.6633 (2) | 0.0502 (6) | |
C18 | 0.1115 (3) | 0.3483 (2) | 0.77727 (18) | 0.0476 (6) | |
C19 | −0.1174 (3) | 0.7185 (3) | 0.6996 (3) | 0.0889 (11) | |
H19A | −0.1636 | 0.8061 | 0.6683 | 0.133* | |
H19B | −0.0557 | 0.7231 | 0.7550 | 0.133* | |
H19C | −0.1991 | 0.6743 | 0.7203 | 0.133* | |
C20 | 0.0084 (4) | 0.3641 (3) | 0.9347 (2) | 0.0903 (11) | |
H20A | 0.0100 | 0.3097 | 0.9964 | 0.135* | |
H20B | −0.0981 | 0.3957 | 0.9109 | 0.135* | |
H20C | 0.0522 | 0.4378 | 0.9424 | 0.135* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0530 (10) | 0.0490 (10) | 0.0779 (12) | −0.0137 (8) | 0.0164 (9) | −0.0206 (9) |
O2 | 0.0565 (11) | 0.0479 (10) | 0.0800 (13) | −0.0046 (8) | −0.0030 (9) | −0.0092 (9) |
O3 | 0.0569 (11) | 0.0819 (14) | 0.0868 (14) | −0.0307 (10) | 0.0089 (10) | −0.0369 (11) |
O4 | 0.0644 (11) | 0.0397 (9) | 0.0540 (10) | −0.0053 (8) | 0.0170 (8) | −0.0083 (8) |
O5 | 0.0575 (11) | 0.0415 (10) | 0.0975 (15) | 0.0038 (8) | 0.0051 (10) | −0.0057 (9) |
O6 | 0.0964 (14) | 0.0523 (11) | 0.0552 (11) | −0.0213 (9) | 0.0284 (10) | −0.0167 (9) |
N1 | 0.0681 (14) | 0.0519 (13) | 0.0554 (13) | −0.0108 (10) | 0.0010 (11) | 0.0034 (11) |
N2 | 0.0712 (15) | 0.0567 (14) | 0.0605 (15) | 0.0004 (11) | −0.0063 (12) | 0.0044 (11) |
N3 | 0.0787 (16) | 0.0608 (15) | 0.0509 (13) | −0.0101 (12) | 0.0026 (12) | 0.0043 (11) |
N4 | 0.0587 (13) | 0.0419 (12) | 0.0521 (12) | −0.0044 (9) | 0.0076 (10) | −0.0068 (10) |
N5 | 0.0473 (12) | 0.0475 (12) | 0.0636 (14) | −0.0126 (9) | 0.0086 (10) | −0.0119 (10) |
N6 | 0.0565 (12) | 0.0512 (12) | 0.0404 (11) | −0.0175 (10) | 0.0048 (9) | −0.0089 (9) |
N7 | 0.0493 (12) | 0.0563 (13) | 0.0559 (13) | −0.0148 (10) | 0.0085 (10) | −0.0183 (10) |
N8 | 0.0472 (12) | 0.0581 (14) | 0.0722 (15) | −0.0139 (10) | −0.0025 (10) | −0.0091 (11) |
N9 | 0.0471 (12) | 0.0578 (14) | 0.0707 (15) | −0.0060 (10) | −0.0077 (11) | −0.0125 (11) |
N10 | 0.0456 (12) | 0.0586 (14) | 0.0686 (14) | −0.0140 (10) | 0.0030 (10) | −0.0182 (11) |
N11 | 0.0427 (11) | 0.0389 (11) | 0.0554 (12) | −0.0058 (8) | 0.0076 (9) | −0.0131 (9) |
N12 | 0.0473 (11) | 0.0384 (11) | 0.0636 (13) | −0.0054 (9) | 0.0091 (10) | −0.0031 (10) |
N13 | 0.0449 (11) | 0.0412 (12) | 0.0692 (14) | −0.0124 (9) | 0.0132 (10) | −0.0201 (10) |
N14 | 0.0549 (12) | 0.0364 (10) | 0.0508 (12) | −0.0125 (9) | 0.0129 (9) | −0.0112 (9) |
C1 | 0.0502 (14) | 0.0448 (14) | 0.0519 (15) | −0.0116 (11) | −0.0042 (11) | −0.0083 (11) |
C2 | 0.0470 (15) | 0.0618 (17) | 0.0740 (19) | −0.0104 (12) | −0.0009 (13) | −0.0250 (15) |
C3 | 0.0610 (17) | 0.084 (2) | 0.0565 (17) | −0.0309 (15) | 0.0131 (13) | −0.0239 (15) |
C4 | 0.078 (2) | 0.078 (2) | 0.0509 (16) | −0.0278 (16) | 0.0046 (15) | 0.0010 (14) |
C5 | 0.0508 (13) | 0.0379 (13) | 0.0452 (13) | −0.0130 (10) | 0.0007 (11) | −0.0079 (10) |
C6 | 0.0552 (15) | 0.0458 (14) | 0.0444 (13) | −0.0163 (11) | 0.0096 (11) | −0.0121 (11) |
C7 | 0.0522 (15) | 0.0479 (14) | 0.0416 (13) | −0.0102 (11) | 0.0026 (11) | −0.0048 (11) |
C8 | 0.0535 (15) | 0.0633 (17) | 0.0402 (13) | −0.0234 (13) | 0.0071 (11) | −0.0170 (12) |
C9 | 0.081 (2) | 0.0472 (16) | 0.093 (2) | −0.0006 (14) | −0.0019 (17) | −0.0126 (15) |
C10 | 0.086 (2) | 0.091 (2) | 0.107 (3) | −0.0486 (18) | 0.0055 (19) | −0.042 (2) |
C11 | 0.0475 (13) | 0.0435 (13) | 0.0377 (12) | −0.0047 (10) | 0.0004 (10) | −0.0097 (10) |
C12 | 0.0704 (17) | 0.0450 (14) | 0.0450 (14) | −0.0045 (12) | −0.0016 (12) | −0.0043 (11) |
C13 | 0.084 (2) | 0.0470 (15) | 0.0602 (17) | −0.0251 (14) | −0.0031 (15) | −0.0060 (13) |
C14 | 0.0645 (18) | 0.0680 (19) | 0.081 (2) | −0.0314 (15) | −0.0083 (15) | −0.0078 (15) |
C15 | 0.0457 (13) | 0.0414 (13) | 0.0383 (12) | −0.0101 (10) | 0.0091 (10) | −0.0110 (10) |
C16 | 0.0418 (12) | 0.0376 (13) | 0.0537 (14) | −0.0127 (10) | 0.0095 (10) | −0.0111 (11) |
C17 | 0.0374 (13) | 0.0380 (13) | 0.0764 (18) | −0.0107 (10) | 0.0032 (12) | −0.0091 (12) |
C18 | 0.0522 (14) | 0.0410 (14) | 0.0558 (15) | −0.0192 (11) | 0.0122 (11) | −0.0146 (11) |
C19 | 0.0633 (19) | 0.0596 (19) | 0.132 (3) | 0.0157 (14) | 0.0124 (19) | −0.0268 (19) |
C20 | 0.124 (3) | 0.084 (2) | 0.072 (2) | −0.029 (2) | 0.047 (2) | −0.0386 (18) |
O1—N4 | 1.372 (2) | N12—C17 | 1.332 (3) |
O1—C6 | 1.386 (3) | N13—C18 | 1.322 (3) |
O2—C7 | 1.324 (3) | N13—C17 | 1.328 (3) |
O2—C9 | 1.443 (3) | N14—C16 | 1.304 (3) |
O3—C8 | 1.321 (3) | N14—C18 | 1.336 (3) |
O3—C10 | 1.444 (3) | C1—C5 | 1.375 (3) |
O4—N11 | 1.372 (2) | C1—C2 | 1.389 (3) |
O4—C16 | 1.387 (3) | C2—C3 | 1.359 (4) |
O5—C17 | 1.315 (3) | C2—H2B | 0.9300 |
O5—C19 | 1.451 (3) | C3—C4 | 1.391 (4) |
O6—C18 | 1.320 (3) | C3—H3B | 0.9300 |
O6—C20 | 1.444 (3) | C4—H4A | 0.9300 |
N1—C4 | 1.325 (3) | C9—H9B | 0.9600 |
N1—C5 | 1.328 (3) | C9—H9C | 0.9600 |
N2—N3 | 1.307 (3) | C9—H9D | 0.9600 |
N2—C1 | 1.379 (3) | C10—H10B | 0.9600 |
N3—N4 | 1.331 (3) | C10—H10C | 0.9600 |
N4—C5 | 1.351 (3) | C10—H10D | 0.9600 |
N5—C6 | 1.312 (3) | C11—C15 | 1.378 (3) |
N5—C7 | 1.331 (3) | C11—C12 | 1.390 (3) |
N6—C7 | 1.321 (3) | C12—C13 | 1.347 (4) |
N6—C8 | 1.322 (3) | C12—H12B | 0.9300 |
N7—C6 | 1.307 (3) | C13—C14 | 1.399 (4) |
N7—C8 | 1.337 (3) | C13—H13B | 0.9300 |
N8—C14 | 1.329 (3) | C14—H14B | 0.9300 |
N8—C15 | 1.330 (3) | C19—H19A | 0.9600 |
N9—N10 | 1.301 (3) | C19—H19B | 0.9600 |
N9—C11 | 1.377 (3) | C19—H19C | 0.9600 |
N10—N11 | 1.333 (3) | C20—H20A | 0.9600 |
N11—C15 | 1.354 (3) | C20—H20B | 0.9600 |
N12—C16 | 1.313 (3) | C20—H20C | 0.9600 |
N4—O1—C6 | 113.69 (18) | O2—C9—H9B | 109.5 |
C7—O2—C9 | 117.1 (2) | O2—C9—H9C | 109.5 |
C8—O3—C10 | 117.9 (2) | H9B—C9—H9C | 109.5 |
N11—O4—C16 | 113.48 (16) | O2—C9—H9D | 109.5 |
C17—O5—C19 | 116.9 (2) | H9B—C9—H9D | 109.5 |
C18—O6—C20 | 117.4 (2) | H9C—C9—H9D | 109.5 |
C4—N1—C5 | 111.4 (2) | O3—C10—H10B | 109.5 |
N3—N2—C1 | 108.1 (2) | O3—C10—H10C | 109.5 |
N2—N3—N4 | 107.2 (2) | H10B—C10—H10C | 109.5 |
N3—N4—C5 | 112.89 (19) | O3—C10—H10D | 109.5 |
N3—N4—O1 | 119.56 (19) | H10B—C10—H10D | 109.5 |
C5—N4—O1 | 127.33 (19) | H10C—C10—H10D | 109.5 |
C6—N5—C7 | 111.3 (2) | N9—C11—C15 | 109.2 (2) |
C7—N6—C8 | 113.5 (2) | N9—C11—C12 | 133.0 (2) |
C6—N7—C8 | 110.9 (2) | C15—C11—C12 | 117.8 (2) |
C14—N8—C15 | 110.9 (2) | C13—C12—C11 | 116.0 (2) |
N10—N9—C11 | 108.31 (19) | C13—C12—H12B | 122.0 |
N9—N10—N11 | 107.28 (19) | C11—C12—H12B | 122.0 |
N10—N11—C15 | 112.81 (18) | C12—C13—C14 | 120.8 (2) |
N10—N11—O4 | 118.89 (18) | C12—C13—H13B | 119.6 |
C15—N11—O4 | 127.96 (19) | C14—C13—H13B | 119.6 |
C16—N12—C17 | 111.4 (2) | N8—C14—C13 | 125.7 (3) |
C18—N13—C17 | 113.5 (2) | N8—C14—H14B | 117.1 |
C16—N14—C18 | 111.0 (2) | C13—C14—H14B | 117.1 |
C5—C1—N2 | 109.0 (2) | N8—C15—N11 | 128.8 (2) |
C5—C1—C2 | 117.7 (2) | N8—C15—C11 | 128.8 (2) |
N2—C1—C2 | 133.3 (2) | N11—C15—C11 | 102.4 (2) |
C3—C2—C1 | 115.6 (2) | N14—C16—N12 | 130.7 (2) |
C3—C2—H2B | 122.2 | N14—C16—O4 | 118.8 (2) |
C1—C2—H2B | 122.2 | N12—C16—O4 | 110.5 (2) |
C2—C3—C4 | 121.2 (3) | O5—C17—N13 | 119.5 (2) |
C2—C3—H3B | 119.4 | O5—C17—N12 | 114.1 (2) |
C4—C3—H3B | 119.4 | N13—C17—N12 | 126.4 (2) |
N1—C4—C3 | 125.2 (3) | O6—C18—N13 | 119.0 (2) |
N1—C4—H4A | 117.4 | O6—C18—N14 | 114.0 (2) |
C3—C4—H4A | 117.4 | N13—C18—N14 | 127.0 (2) |
N1—C5—N4 | 128.4 (2) | O5—C19—H19A | 109.5 |
N1—C5—C1 | 128.9 (2) | O5—C19—H19B | 109.5 |
N4—C5—C1 | 102.76 (19) | H19A—C19—H19B | 109.5 |
N7—C6—N5 | 130.5 (2) | O5—C19—H19C | 109.5 |
N7—C6—O1 | 118.7 (2) | H19A—C19—H19C | 109.5 |
N5—C6—O1 | 110.8 (2) | H19B—C19—H19C | 109.5 |
N6—C7—O2 | 119.5 (2) | O6—C20—H20A | 109.5 |
N6—C7—N5 | 126.7 (2) | O6—C20—H20B | 109.5 |
O2—C7—N5 | 113.8 (2) | H20A—C20—H20B | 109.5 |
O3—C8—N6 | 119.5 (2) | O6—C20—H20C | 109.5 |
O3—C8—N7 | 113.5 (2) | H20A—C20—H20C | 109.5 |
N6—C8—N7 | 127.0 (2) | H20B—C20—H20C | 109.5 |
C1—N2—N3—N4 | 0.3 (3) | C10—O3—C8—N7 | −178.8 (2) |
N2—N3—N4—C5 | 0.0 (3) | C7—N6—C8—O3 | −177.3 (2) |
N2—N3—N4—O1 | 175.0 (2) | C7—N6—C8—N7 | 3.2 (3) |
C6—O1—N4—N3 | 109.2 (2) | C6—N7—C8—O3 | 179.5 (2) |
C6—O1—N4—C5 | −76.6 (3) | C6—N7—C8—N6 | −0.9 (3) |
C11—N9—N10—N11 | 0.0 (3) | N10—N9—C11—C15 | 0.3 (3) |
N9—N10—N11—C15 | −0.2 (3) | N10—N9—C11—C12 | 179.3 (2) |
N9—N10—N11—O4 | −173.99 (18) | N9—C11—C12—C13 | −179.5 (3) |
C16—O4—N11—N10 | −98.7 (2) | C15—C11—C12—C13 | −0.5 (3) |
C16—O4—N11—C15 | 88.6 (3) | C11—C12—C13—C14 | 0.0 (4) |
N3—N2—C1—C5 | −0.5 (3) | C15—N8—C14—C13 | 0.1 (4) |
N3—N2—C1—C2 | 179.7 (3) | C12—C13—C14—N8 | 0.3 (5) |
C5—C1—C2—C3 | 1.4 (3) | C14—N8—C15—N11 | 180.0 (2) |
N2—C1—C2—C3 | −178.9 (3) | C14—N8—C15—C11 | −0.8 (4) |
C1—C2—C3—C4 | −1.6 (4) | N10—N11—C15—N8 | 179.7 (2) |
C5—N1—C4—C3 | 0.4 (4) | O4—N11—C15—N8 | −7.2 (4) |
C2—C3—C4—N1 | 0.8 (5) | N10—N11—C15—C11 | 0.3 (2) |
C4—N1—C5—N4 | 178.7 (2) | O4—N11—C15—C11 | 173.44 (19) |
C4—N1—C5—C1 | −0.6 (4) | N9—C11—C15—N8 | −179.7 (2) |
N3—N4—C5—N1 | −179.7 (2) | C12—C11—C15—N8 | 1.0 (4) |
O1—N4—C5—N1 | 5.7 (4) | N9—C11—C15—N11 | −0.3 (2) |
N3—N4—C5—C1 | −0.3 (3) | C12—C11—C15—N11 | −179.6 (2) |
O1—N4—C5—C1 | −174.8 (2) | C18—N14—C16—N12 | 1.4 (4) |
N2—C1—C5—N1 | 179.9 (2) | C18—N14—C16—O4 | −178.2 (2) |
C2—C1—C5—N1 | −0.3 (4) | C17—N12—C16—N14 | −2.2 (4) |
N2—C1—C5—N4 | 0.5 (3) | C17—N12—C16—O4 | 177.40 (19) |
C2—C1—C5—N4 | −179.7 (2) | N11—O4—C16—N14 | −0.8 (3) |
C8—N7—C6—N5 | −2.7 (4) | N11—O4—C16—N12 | 179.54 (18) |
C8—N7—C6—O1 | 177.1 (2) | C19—O5—C17—N13 | 1.0 (3) |
C7—N5—C6—N7 | 3.3 (4) | C19—O5—C17—N12 | −179.1 (2) |
C7—N5—C6—O1 | −176.49 (19) | C18—N13—C17—O5 | −178.5 (2) |
N4—O1—C6—N7 | −9.7 (3) | C18—N13—C17—N12 | 1.6 (4) |
N4—O1—C6—N5 | 170.17 (18) | C16—N12—C17—O5 | −179.4 (2) |
C8—N6—C7—O2 | 177.9 (2) | C16—N12—C17—N13 | 0.5 (4) |
C8—N6—C7—N5 | −2.5 (3) | C20—O6—C18—N13 | −4.5 (4) |
C9—O2—C7—N6 | −0.6 (3) | C20—O6—C18—N14 | 176.1 (2) |
C9—O2—C7—N5 | 179.7 (2) | C17—N13—C18—O6 | 178.1 (2) |
C6—N5—C7—N6 | −0.4 (3) | C17—N13—C18—N14 | −2.6 (3) |
C6—N5—C7—O2 | 179.3 (2) | C16—N14—C18—O6 | −179.4 (2) |
C10—O3—C8—N6 | 1.7 (4) | C16—N14—C18—N13 | 1.3 (3) |