Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805033908/su6227sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805033908/su6227Isup2.hkl |
CCDC reference: 289897
Data collection: CAD-4-PC Software (Nonius, 1996); cell refinement: CAD-4-PC Software; data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
C16H13N3O2 | F(000) = 584 |
Mr = 279.29 | Dx = 1.348 Mg m−3 |
Monoclinic, Pc | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: P -2yc | Cell parameters from 25 reflections |
a = 7.439 (1) Å | θ = 3.9–19.4° |
b = 11.215 (1) Å | µ = 0.75 mm−1 |
c = 16.541 (1) Å | T = 299 K |
β = 93.96 (1)° | Needle, orange |
V = 1376.7 (2) Å3 | 0.68 × 0.20 × 0.10 mm |
Z = 4 |
Nonius CAD-4 diffractometer | Rint = 0.014 |
Radiation source: fine-focus sealed tube | θmax = 67.9°, θmin = 3.9° |
Graphite monochromator | h = −8→0 |
ω/2θ scans | k = −13→1 |
2913 measured reflections | l = −19→19 |
2497 independent reflections | 3 standard reflections every 120 min |
2233 reflections with I > 2σ(I) | intensity decay: 1.0% |
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) = 0.119 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0853P)2 + 0.028P] where P = (Fo2 + 2Fc2)/3 |
2497 reflections | (Δ/σ)max = 0.001 |
379 parameters | Δρmax = 0.16 e Å−3 |
2 restraints | Δρmin = −0.20 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 | 0.6479 (4) | 0.0074 (2) | 0.56618 (15) | 0.0832 (8) | |
O2 | 0.7853 (5) | −0.1592 (3) | 0.55330 (19) | 0.0948 (9) | |
N1 | 0.8025 (3) | 0.1310 (2) | 0.43538 (14) | 0.0483 (5) | |
N2 | 0.9293 (3) | 0.3181 (3) | 0.43035 (18) | 0.0605 (7) | |
H2N | 0.9479 | 0.3789 | 0.4002 | 0.073* | |
N3 | 0.7053 (4) | −0.0717 (2) | 0.52474 (16) | 0.0588 (6) | |
C1 | 0.7217 (3) | 0.0378 (3) | 0.39533 (16) | 0.0462 (6) | |
C2 | 0.8469 (4) | 0.2242 (3) | 0.39204 (18) | 0.0505 (7) | |
C3 | 0.8129 (4) | 0.2303 (3) | 0.3059 (2) | 0.0604 (8) | |
H3 | 0.8457 | 0.2976 | 0.2775 | 0.073* | |
C4 | 0.7332 (4) | 0.1377 (3) | 0.26650 (19) | 0.0620 (8) | |
H4 | 0.7107 | 0.1407 | 0.2105 | 0.074* | |
C5 | 0.6829 (4) | 0.0351 (3) | 0.30994 (17) | 0.0529 (7) | |
C6 | 0.6003 (4) | −0.0644 (3) | 0.2731 (2) | 0.0651 (9) | |
H6 | 0.5757 | −0.0644 | 0.2172 | 0.078* | |
C7 | 0.5544 (5) | −0.1619 (3) | 0.3166 (2) | 0.0661 (8) | |
H7 | 0.4986 | −0.2270 | 0.2907 | 0.079* | |
C8 | 0.5923 (4) | −0.1624 (3) | 0.4001 (2) | 0.0603 (8) | |
H8 | 0.5636 | −0.2287 | 0.4304 | 0.072* | |
C9 | 0.6720 (4) | −0.0653 (3) | 0.43729 (18) | 0.0504 (6) | |
C10 | 0.9608 (4) | 0.3268 (3) | 0.5174 (2) | 0.0646 (8) | |
H10A | 1.0658 | 0.3764 | 0.5301 | 0.078* | |
H10B | 0.9865 | 0.2480 | 0.5395 | 0.078* | |
C11 | 0.8005 (4) | 0.3792 (3) | 0.55762 (18) | 0.0563 (7) | |
C12 | 0.7751 (7) | 0.5012 (3) | 0.5620 (3) | 0.0828 (11) | |
H12 | 0.8612 | 0.5523 | 0.5430 | 0.099* | |
C13 | 0.6242 (9) | 0.5482 (5) | 0.5940 (3) | 0.1075 (18) | |
H13 | 0.6086 | 0.6304 | 0.5963 | 0.129* | |
C14 | 0.4991 (8) | 0.4743 (6) | 0.6219 (3) | 0.1050 (17) | |
H14 | 0.3967 | 0.5060 | 0.6430 | 0.126* | |
C15 | 0.5216 (6) | 0.3532 (5) | 0.6195 (2) | 0.0809 (11) | |
H15 | 0.4355 | 0.3032 | 0.6395 | 0.097* | |
C16 | 0.6725 (5) | 0.3054 (3) | 0.58721 (19) | 0.0618 (8) | |
H16 | 0.6874 | 0.2231 | 0.5855 | 0.074* | |
O3 | 0.1486 (5) | 0.2968 (2) | 0.13557 (17) | 0.0872 (8) | |
O4 | 0.3004 (6) | 0.1769 (4) | 0.0676 (2) | 0.1184 (12) | |
N4 | 0.2999 (3) | 0.2281 (2) | 0.29424 (14) | 0.0507 (6) | |
N5 | 0.4277 (4) | 0.3376 (3) | 0.40077 (18) | 0.0663 (7) | |
H5N | 0.4694 | 0.3440 | 0.4502 | 0.080* | |
N6 | 0.2144 (4) | 0.2006 (3) | 0.12596 (18) | 0.0671 (7) | |
C17 | 0.2232 (3) | 0.1241 (3) | 0.26696 (19) | 0.0499 (6) | |
C18 | 0.3450 (4) | 0.2359 (3) | 0.37237 (19) | 0.0549 (7) | |
C19 | 0.3129 (4) | 0.1431 (4) | 0.4288 (2) | 0.0657 (9) | |
H19 | 0.3458 | 0.1528 | 0.4836 | 0.079* | |
C20 | 0.2355 (4) | 0.0426 (4) | 0.4017 (2) | 0.0663 (9) | |
H20 | 0.2132 | −0.0181 | 0.4380 | 0.080* | |
C21 | 0.1865 (4) | 0.0272 (3) | 0.3178 (2) | 0.0598 (8) | |
C22 | 0.1118 (5) | −0.0777 (3) | 0.2848 (3) | 0.0768 (11) | |
H22 | 0.0852 | −0.1396 | 0.3194 | 0.092* | |
C23 | 0.0767 (6) | −0.0923 (4) | 0.2038 (3) | 0.0828 (11) | |
H23 | 0.0276 | −0.1633 | 0.1834 | 0.099* | |
C24 | 0.1147 (5) | −0.0001 (3) | 0.1517 (3) | 0.0724 (9) | |
H24 | 0.0936 | −0.0093 | 0.0960 | 0.087* | |
C25 | 0.1841 (4) | 0.1053 (3) | 0.1832 (2) | 0.0567 (7) | |
C26 | 0.4415 (4) | 0.4442 (3) | 0.3536 (2) | 0.0658 (8) | |
H26A | 0.4711 | 0.4229 | 0.2993 | 0.079* | |
H26B | 0.5388 | 0.4931 | 0.3775 | 0.079* | |
C27 | 0.2689 (4) | 0.5159 (3) | 0.3488 (2) | 0.0547 (7) | |
C28 | 0.2263 (5) | 0.5870 (3) | 0.4127 (2) | 0.0669 (9) | |
H28 | 0.3081 | 0.5953 | 0.4575 | 0.080* | |
C29 | 0.0630 (7) | 0.6461 (3) | 0.4108 (3) | 0.0805 (11) | |
H29 | 0.0359 | 0.6943 | 0.4540 | 0.097* | |
C30 | −0.0576 (7) | 0.6340 (3) | 0.3463 (3) | 0.0839 (12) | |
H30 | −0.1672 | 0.6740 | 0.3457 | 0.101* | |
C31 | −0.0202 (5) | 0.5637 (4) | 0.2819 (3) | 0.0747 (10) | |
H31 | −0.1038 | 0.5558 | 0.2378 | 0.090* | |
C32 | 0.1439 (5) | 0.5041 (3) | 0.2831 (2) | 0.0602 (8) | |
H32 | 0.1700 | 0.4561 | 0.2396 | 0.072* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.123 (2) | 0.0750 (15) | 0.0531 (13) | −0.0014 (15) | 0.0195 (14) | 0.0002 (12) |
O2 | 0.117 (2) | 0.0860 (18) | 0.0783 (18) | 0.0235 (18) | −0.0164 (17) | 0.0178 (15) |
N1 | 0.0330 (11) | 0.0640 (14) | 0.0488 (12) | 0.0063 (10) | 0.0094 (9) | 0.0059 (11) |
N2 | 0.0479 (14) | 0.0699 (16) | 0.0655 (15) | −0.0020 (12) | 0.0175 (12) | 0.0104 (13) |
N3 | 0.0659 (17) | 0.0584 (15) | 0.0517 (14) | −0.0065 (13) | 0.0005 (12) | 0.0047 (12) |
C1 | 0.0317 (13) | 0.0605 (16) | 0.0472 (14) | 0.0124 (11) | 0.0089 (11) | 0.0014 (12) |
C2 | 0.0308 (13) | 0.0645 (18) | 0.0578 (16) | 0.0076 (12) | 0.0143 (11) | 0.0083 (14) |
C3 | 0.0430 (16) | 0.081 (2) | 0.0595 (18) | 0.0107 (15) | 0.0206 (14) | 0.0172 (16) |
C4 | 0.0508 (17) | 0.092 (2) | 0.0441 (15) | 0.0162 (17) | 0.0102 (13) | 0.0079 (16) |
C5 | 0.0352 (14) | 0.078 (2) | 0.0468 (14) | 0.0160 (13) | 0.0105 (11) | 0.0006 (14) |
C6 | 0.0529 (18) | 0.091 (2) | 0.0516 (17) | 0.0201 (17) | 0.0028 (13) | −0.0132 (17) |
C7 | 0.0566 (18) | 0.071 (2) | 0.070 (2) | 0.0100 (16) | −0.0005 (15) | −0.0149 (17) |
C8 | 0.0573 (19) | 0.0599 (17) | 0.0637 (19) | 0.0103 (15) | 0.0033 (14) | −0.0051 (14) |
C9 | 0.0406 (14) | 0.0586 (16) | 0.0526 (15) | 0.0109 (12) | 0.0070 (12) | −0.0017 (12) |
C10 | 0.0443 (17) | 0.077 (2) | 0.072 (2) | −0.0063 (15) | −0.0015 (14) | 0.0044 (17) |
C11 | 0.0547 (16) | 0.0664 (17) | 0.0471 (15) | −0.0025 (14) | −0.0022 (12) | 0.0017 (13) |
C12 | 0.108 (3) | 0.065 (2) | 0.076 (2) | −0.003 (2) | 0.017 (2) | 0.0035 (18) |
C13 | 0.155 (5) | 0.086 (3) | 0.084 (3) | 0.037 (3) | 0.027 (3) | −0.001 (2) |
C14 | 0.115 (4) | 0.139 (5) | 0.063 (2) | 0.048 (4) | 0.021 (2) | −0.003 (3) |
C15 | 0.068 (2) | 0.118 (3) | 0.058 (2) | 0.004 (2) | 0.0135 (16) | 0.002 (2) |
C16 | 0.0587 (18) | 0.073 (2) | 0.0536 (16) | −0.0015 (16) | 0.0025 (13) | −0.0012 (15) |
O3 | 0.123 (2) | 0.0691 (15) | 0.0680 (15) | 0.0051 (16) | −0.0037 (15) | 0.0073 (13) |
O4 | 0.135 (3) | 0.136 (3) | 0.091 (2) | 0.024 (3) | 0.054 (2) | 0.022 (2) |
N4 | 0.0319 (11) | 0.0672 (15) | 0.0533 (13) | 0.0110 (10) | 0.0047 (10) | 0.0053 (11) |
N5 | 0.0482 (15) | 0.0868 (19) | 0.0623 (16) | 0.0112 (14) | −0.0082 (12) | −0.0016 (14) |
N6 | 0.0672 (18) | 0.0761 (19) | 0.0576 (15) | 0.0016 (15) | 0.0019 (13) | 0.0001 (14) |
C17 | 0.0294 (13) | 0.0602 (16) | 0.0605 (16) | 0.0130 (12) | 0.0068 (11) | 0.0065 (13) |
C18 | 0.0326 (14) | 0.075 (2) | 0.0570 (16) | 0.0182 (13) | 0.0033 (12) | 0.0036 (14) |
C19 | 0.0476 (17) | 0.095 (3) | 0.0547 (17) | 0.0268 (18) | 0.0067 (13) | 0.0130 (17) |
C20 | 0.0506 (17) | 0.078 (2) | 0.073 (2) | 0.0183 (16) | 0.0175 (15) | 0.0277 (18) |
C21 | 0.0369 (15) | 0.0675 (19) | 0.076 (2) | 0.0123 (13) | 0.0114 (14) | 0.0179 (16) |
C22 | 0.057 (2) | 0.065 (2) | 0.110 (3) | 0.0013 (17) | 0.018 (2) | 0.018 (2) |
C23 | 0.064 (2) | 0.072 (2) | 0.111 (3) | −0.0054 (19) | 0.001 (2) | −0.001 (2) |
C24 | 0.061 (2) | 0.072 (2) | 0.084 (2) | 0.0044 (17) | −0.0035 (18) | −0.0066 (18) |
C25 | 0.0414 (15) | 0.0633 (17) | 0.0661 (18) | 0.0105 (13) | 0.0077 (13) | 0.0053 (14) |
C26 | 0.0383 (16) | 0.084 (2) | 0.076 (2) | −0.0065 (16) | 0.0044 (13) | −0.0047 (19) |
C27 | 0.0516 (16) | 0.0555 (16) | 0.0575 (16) | −0.0101 (13) | 0.0066 (12) | 0.0024 (13) |
C28 | 0.079 (2) | 0.0577 (18) | 0.0638 (19) | −0.0130 (17) | 0.0030 (17) | −0.0019 (14) |
C29 | 0.108 (3) | 0.0545 (18) | 0.082 (2) | 0.008 (2) | 0.031 (2) | −0.0018 (17) |
C30 | 0.081 (3) | 0.062 (2) | 0.110 (3) | 0.021 (2) | 0.020 (2) | 0.012 (2) |
C31 | 0.065 (2) | 0.072 (2) | 0.085 (2) | 0.0080 (18) | −0.0098 (18) | 0.0122 (19) |
C32 | 0.0598 (18) | 0.0660 (18) | 0.0555 (16) | 0.0010 (15) | 0.0076 (13) | 0.0019 (14) |
O1—N3 | 1.217 (4) | O3—N6 | 1.200 (4) |
O2—N3 | 1.225 (4) | O4—N6 | 1.224 (4) |
N1—C2 | 1.323 (4) | N4—C18 | 1.316 (4) |
N1—C1 | 1.356 (4) | N4—C17 | 1.362 (4) |
N2—C2 | 1.354 (4) | N5—C18 | 1.364 (5) |
N2—C10 | 1.446 (5) | N5—C26 | 1.435 (5) |
N2—H2N | 0.8617 | N5—H5N | 0.8571 |
N3—C9 | 1.452 (4) | N6—C25 | 1.455 (4) |
C1—C9 | 1.411 (4) | C17—C21 | 1.412 (4) |
C1—C5 | 1.422 (4) | C17—C25 | 1.412 (4) |
C2—C3 | 1.432 (4) | C18—C19 | 1.429 (5) |
C3—C4 | 1.342 (5) | C19—C20 | 1.328 (5) |
C3—H3 | 0.9300 | C19—H19 | 0.9300 |
C4—C5 | 1.420 (5) | C20—C21 | 1.422 (5) |
C4—H4 | 0.9300 | C20—H20 | 0.9300 |
C5—C6 | 1.393 (5) | C21—C22 | 1.396 (6) |
C6—C7 | 1.365 (6) | C22—C23 | 1.357 (6) |
C6—H6 | 0.9300 | C22—H22 | 0.9300 |
C7—C8 | 1.390 (5) | C23—C24 | 1.387 (6) |
C7—H7 | 0.9300 | C23—H23 | 0.9300 |
C8—C9 | 1.366 (4) | C24—C25 | 1.377 (5) |
C8—H8 | 0.9300 | C24—H24 | 0.9300 |
C10—C11 | 1.522 (5) | C26—C27 | 1.512 (5) |
C10—H10A | 0.9700 | C26—H26A | 0.9700 |
C10—H10B | 0.9700 | C26—H26B | 0.9700 |
C11—C16 | 1.377 (5) | C27—C28 | 1.379 (5) |
C11—C12 | 1.385 (5) | C27—C32 | 1.388 (5) |
C12—C13 | 1.378 (7) | C28—C29 | 1.382 (6) |
C12—H12 | 0.9300 | C28—H28 | 0.9300 |
C13—C14 | 1.351 (8) | C29—C30 | 1.352 (7) |
C13—H13 | 0.9300 | C29—H29 | 0.9300 |
C14—C15 | 1.369 (7) | C30—C31 | 1.370 (6) |
C14—H14 | 0.9300 | C30—H30 | 0.9300 |
C15—C16 | 1.384 (5) | C31—C32 | 1.391 (5) |
C15—H15 | 0.9300 | C31—H31 | 0.9300 |
C16—H16 | 0.9300 | C32—H32 | 0.9300 |
C2—N1—C1 | 117.6 (2) | C18—N4—C17 | 117.1 (3) |
C2—N2—C10 | 123.8 (3) | C18—N5—C26 | 123.9 (3) |
C2—N2—H2N | 115.5 | C18—N5—H5N | 121.5 |
C10—N2—H2N | 120.1 | C26—N5—H5N | 114.5 |
O1—N3—O2 | 123.2 (3) | O3—N6—O4 | 122.7 (4) |
O1—N3—C9 | 118.9 (3) | O3—N6—C25 | 119.4 (3) |
O2—N3—C9 | 117.9 (3) | O4—N6—C25 | 117.8 (3) |
N1—C1—C9 | 120.9 (2) | N4—C17—C21 | 123.8 (3) |
N1—C1—C5 | 123.7 (3) | N4—C17—C25 | 120.4 (3) |
C9—C1—C5 | 115.4 (3) | C21—C17—C25 | 115.7 (3) |
N1—C2—N2 | 118.9 (3) | N4—C18—N5 | 118.2 (3) |
N1—C2—C3 | 122.9 (3) | N4—C18—C19 | 123.4 (3) |
N2—C2—C3 | 118.2 (3) | N5—C18—C19 | 118.4 (3) |
C4—C3—C2 | 119.2 (3) | C20—C19—C18 | 119.1 (3) |
C4—C3—H3 | 120.4 | C20—C19—H19 | 120.4 |
C2—C3—H3 | 120.4 | C18—C19—H19 | 120.4 |
C3—C4—C5 | 120.3 (3) | C19—C20—C21 | 120.5 (3) |
C3—C4—H4 | 119.9 | C19—C20—H20 | 119.7 |
C5—C4—H4 | 119.9 | C21—C20—H20 | 119.7 |
C6—C5—C4 | 123.4 (3) | C22—C21—C17 | 120.3 (4) |
C6—C5—C1 | 120.3 (3) | C22—C21—C20 | 123.6 (3) |
C4—C5—C1 | 116.3 (3) | C17—C21—C20 | 116.1 (3) |
C7—C6—C5 | 122.0 (3) | C23—C22—C21 | 122.1 (4) |
C7—C6—H6 | 119.0 | C23—C22—H22 | 118.9 |
C5—C6—H6 | 119.0 | C21—C22—H22 | 118.9 |
C6—C7—C8 | 119.1 (3) | C22—C23—C24 | 119.3 (4) |
C6—C7—H7 | 120.5 | C22—C23—H23 | 120.4 |
C8—C7—H7 | 120.5 | C24—C23—H23 | 120.4 |
C9—C8—C7 | 119.8 (3) | C25—C24—C23 | 119.5 (4) |
C9—C8—H8 | 120.1 | C25—C24—H24 | 120.2 |
C7—C8—H8 | 120.1 | C23—C24—H24 | 120.2 |
C8—C9—C1 | 123.5 (3) | C24—C25—C17 | 123.0 (3) |
C8—C9—N3 | 116.6 (3) | C24—C25—N6 | 117.1 (3) |
C1—C9—N3 | 119.9 (3) | C17—C25—N6 | 119.9 (3) |
N2—C10—C11 | 112.5 (3) | N5—C26—C27 | 112.3 (3) |
N2—C10—H10A | 109.1 | N5—C26—H26A | 109.2 |
C11—C10—H10A | 109.1 | C27—C26—H26A | 109.2 |
N2—C10—H10B | 109.1 | N5—C26—H26B | 109.2 |
C11—C10—H10B | 109.1 | C27—C26—H26B | 109.2 |
H10A—C10—H10B | 107.8 | H26A—C26—H26B | 107.9 |
C16—C11—C12 | 118.4 (4) | C28—C27—C32 | 118.6 (3) |
C16—C11—C10 | 120.4 (3) | C28—C27—C26 | 120.4 (3) |
C12—C11—C10 | 121.2 (3) | C32—C27—C26 | 120.8 (3) |
C13—C12—C11 | 121.1 (4) | C27—C28—C29 | 120.5 (4) |
C13—C12—H12 | 119.5 | C27—C28—H28 | 119.7 |
C11—C12—H12 | 119.5 | C29—C28—H28 | 119.7 |
C14—C13—C12 | 119.7 (5) | C30—C29—C28 | 120.3 (4) |
C14—C13—H13 | 120.2 | C30—C29—H29 | 119.9 |
C12—C13—H13 | 120.2 | C28—C29—H29 | 119.9 |
C13—C14—C15 | 120.6 (5) | C29—C30—C31 | 120.8 (4) |
C13—C14—H14 | 119.7 | C29—C30—H30 | 119.6 |
C15—C14—H14 | 119.7 | C31—C30—H30 | 119.6 |
C14—C15—C16 | 120.0 (4) | C30—C31—C32 | 119.4 (4) |
C14—C15—H15 | 120.0 | C30—C31—H31 | 120.3 |
C16—C15—H15 | 120.0 | C32—C31—H31 | 120.3 |
C11—C16—C15 | 120.2 (4) | C27—C32—C31 | 120.4 (3) |
C11—C16—H16 | 119.9 | C27—C32—H32 | 119.8 |
C15—C16—H16 | 119.9 | C31—C32—H32 | 119.8 |
C2—N1—C1—C9 | 179.4 (2) | C18—N4—C17—C21 | 1.6 (4) |
C2—N1—C1—C5 | 0.2 (3) | C18—N4—C17—C25 | −175.0 (2) |
C1—N1—C2—N2 | −179.4 (2) | C17—N4—C18—N5 | 177.8 (2) |
C1—N1—C2—C3 | 0.1 (4) | C17—N4—C18—C19 | −1.8 (4) |
C10—N2—C2—N1 | −4.6 (4) | C26—N5—C18—N4 | 10.9 (4) |
C10—N2—C2—C3 | 175.8 (3) | C26—N5—C18—C19 | −169.5 (3) |
N1—C2—C3—C4 | −0.3 (4) | N4—C18—C19—C20 | 0.8 (4) |
N2—C2—C3—C4 | 179.3 (3) | N5—C18—C19—C20 | −178.8 (3) |
C2—C3—C4—C5 | 0.1 (4) | C18—C19—C20—C21 | 0.5 (4) |
C3—C4—C5—C6 | −179.8 (3) | N4—C17—C21—C22 | −178.3 (3) |
C3—C4—C5—C1 | 0.1 (4) | C25—C17—C21—C22 | −1.6 (4) |
N1—C1—C5—C6 | 179.6 (3) | N4—C17—C21—C20 | −0.4 (4) |
C9—C1—C5—C6 | 0.4 (4) | C25—C17—C21—C20 | 176.4 (3) |
N1—C1—C5—C4 | −0.3 (4) | C19—C20—C21—C22 | 177.2 (3) |
C9—C1—C5—C4 | −179.5 (2) | C19—C20—C21—C17 | −0.7 (4) |
C4—C5—C6—C7 | 179.7 (3) | C17—C21—C22—C23 | 1.9 (5) |
C1—C5—C6—C7 | −0.2 (4) | C20—C21—C22—C23 | −175.9 (3) |
C5—C6—C7—C8 | −0.5 (5) | C21—C22—C23—C24 | −0.5 (6) |
C6—C7—C8—C9 | 1.0 (5) | C22—C23—C24—C25 | −1.3 (6) |
C7—C8—C9—C1 | −0.8 (4) | C23—C24—C25—C17 | 1.6 (5) |
C7—C8—C9—N3 | 179.2 (3) | C23—C24—C25—N6 | −177.5 (3) |
N1—C1—C9—C8 | −179.1 (3) | N4—C17—C25—C24 | 176.7 (3) |
C5—C1—C9—C8 | 0.1 (4) | C21—C17—C25—C24 | −0.1 (4) |
N1—C1—C9—N3 | 0.9 (4) | N4—C17—C25—N6 | −4.2 (4) |
C5—C1—C9—N3 | −179.9 (2) | C21—C17—C25—N6 | 179.0 (3) |
O1—N3—C9—C8 | −126.1 (3) | O3—N6—C25—C24 | 125.7 (3) |
O2—N3—C9—C8 | 51.6 (4) | O4—N6—C25—C24 | −51.1 (5) |
O1—N3—C9—C1 | 53.9 (4) | O3—N6—C25—C17 | −53.4 (4) |
O2—N3—C9—C1 | −128.4 (3) | O4—N6—C25—C17 | 129.8 (4) |
C2—N2—C10—C11 | −86.2 (4) | C18—N5—C26—C27 | 79.1 (4) |
N2—C10—C11—C16 | 93.7 (4) | N5—C26—C27—C28 | 78.8 (4) |
N2—C10—C11—C12 | −83.2 (4) | N5—C26—C27—C32 | −96.0 (4) |
C16—C11—C12—C13 | −1.0 (6) | C32—C27—C28—C29 | −0.6 (5) |
C10—C11—C12—C13 | 176.0 (4) | C26—C27—C28—C29 | −175.5 (3) |
C11—C12—C13—C14 | 0.3 (8) | C27—C28—C29—C30 | 0.5 (6) |
C12—C13—C14—C15 | 0.6 (8) | C28—C29—C30—C31 | −0.2 (6) |
C13—C14—C15—C16 | −0.8 (7) | C29—C30—C31—C32 | 0.0 (6) |
C12—C11—C16—C15 | 0.8 (5) | C28—C27—C32—C31 | 0.4 (5) |
C10—C11—C16—C15 | −176.2 (3) | C26—C27—C32—C31 | 175.3 (3) |
C14—C15—C16—C11 | 0.1 (6) | C30—C31—C32—C27 | −0.1 (5) |