Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805023652/hg6209sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805023652/hg6209Isup2.hkl |
CCDC reference: 283922
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
C5H16N2+·2C6H2N3O7? | F(000) = 1160 |
Mr = 560.41 | Dx = 1.562 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 11.3271 (14) Å | θ = 15–50° |
b = 26.9657 (12) Å | µ = 1.21 mm−1 |
c = 8.0667 (6) Å | T = 293 K |
β = 104.764 (4)° | Needle, red |
V = 2382.6 (4) Å3 | 0.25 × 0.20 × 0.15 mm |
Z = 4 |
Enraf–Nonius CAD-4 diffractometer | 3473 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.040 |
Graphite monochromator | θmax = 74.9°, θmin = 3.3° |
ω–2θ scans | h = −14→5 |
Absorption correction: ψ scan (North et al., 1968) | k = −33→10 |
Tmin = 0.760, Tmax = 0.835 | l = −9→10 |
5478 measured reflections | 2 standard reflections every 100 reflections |
4900 independent reflections | intensity decay: 1% |
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)] = 0.060 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.171 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.092P)2 + 0.6389P] where P = (Fo2 + 2Fc2)/3 |
4900 reflections | (Δ/σ)max < 0.001 |
408 parameters | Δρmax = 0.42 e Å−3 |
0 restraints | Δρmin = −0.32 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 | ||
O1A | 0.10400 (19) | 0.33171 (11) | 0.7074 (3) | 0.0893 (9) | |
O2A | 0.0216 (2) | 0.31823 (14) | 0.9837 (3) | 0.1053 (10) | |
O3A | 0.1382 (3) | 0.28729 (14) | 1.2041 (4) | 0.1153 (12) | |
O4A | 0.5704 (2) | 0.28269 (11) | 1.2853 (4) | 0.0970 (9) | |
O5A | 0.6501 (2) | 0.30896 (10) | 1.0859 (3) | 0.0796 (7) | |
O6A | 0.3948 (3) | 0.32344 (14) | 0.5184 (4) | 0.1110 (11) | |
O7A | 0.2359 (2) | 0.36781 (10) | 0.5005 (3) | 0.0841 (7) | |
N1A | 0.1217 (2) | 0.30411 (10) | 1.0615 (4) | 0.0657 (7) | |
N2A | 0.5613 (2) | 0.29867 (9) | 1.1414 (4) | 0.0649 (7) | |
N3A | 0.3140 (2) | 0.33907 (10) | 0.5781 (3) | 0.0640 (7) | |
C1A | 0.2046 (2) | 0.32357 (10) | 0.8078 (4) | 0.0540 (7) | |
C2A | 0.2247 (2) | 0.30947 (10) | 0.9860 (4) | 0.0520 (6) | |
C3A | 0.3397 (3) | 0.30140 (10) | 1.0925 (4) | 0.0544 (7) | |
C4A | 0.4402 (2) | 0.30583 (9) | 1.0298 (4) | 0.0522 (7) | |
C5A | 0.4303 (2) | 0.31729 (10) | 0.8598 (4) | 0.0510 (6) | |
C6A | 0.3174 (2) | 0.32632 (9) | 0.7549 (3) | 0.0498 (6) | |
H3A | 0.337 (3) | 0.2953 (12) | 1.193 (4) | 0.058 (9)* | |
H5A | 0.500 (3) | 0.3190 (10) | 0.813 (4) | 0.053 (8)* | |
O1B | 0.15789 (14) | 0.47321 (7) | −0.3495 (2) | 0.0445 (4) | |
O2B | 0.1033 (2) | 0.47287 (11) | −0.0399 (3) | 0.0889 (9) | |
O3B | 0.20159 (19) | 0.41760 (8) | 0.1245 (3) | 0.0614 (5) | |
O4B | 0.63352 (19) | 0.41767 (9) | 0.2019 (2) | 0.0698 (6) | |
O5B | 0.70768 (18) | 0.42925 (10) | −0.0153 (3) | 0.0758 (7) | |
O6B | 0.43662 (18) | 0.45323 (8) | −0.5684 (2) | 0.0610 (5) | |
O7B | 0.28214 (18) | 0.50057 (9) | −0.5804 (2) | 0.0664 (6) | |
N1B | 0.19081 (19) | 0.44619 (8) | 0.0045 (3) | 0.0468 (5) | |
N2B | 0.62181 (19) | 0.42712 (8) | 0.0513 (3) | 0.0486 (5) | |
N3B | 0.36183 (18) | 0.47231 (8) | −0.5032 (2) | 0.0450 (5) | |
C1B | 0.26255 (19) | 0.46288 (8) | −0.2599 (3) | 0.0343 (4) | |
C2B | 0.2891 (2) | 0.44868 (8) | −0.0814 (3) | 0.0363 (5) | |
C3B | 0.4031 (2) | 0.43643 (8) | 0.0182 (3) | 0.0376 (5) | |
C4B | 0.5005 (2) | 0.43756 (8) | −0.0543 (3) | 0.0373 (5) | |
C5B | 0.4848 (2) | 0.44918 (8) | −0.2263 (3) | 0.0366 (5) | |
C6B | 0.3705 (2) | 0.46119 (8) | −0.3232 (3) | 0.0364 (5) | |
H3B | 0.411 (3) | 0.4273 (12) | 0.128 (4) | 0.067 (9)* | |
H5B | 0.549 (2) | 0.4498 (8) | −0.270 (3) | 0.031 (6)* | |
N4 | 0.0200 (2) | 0.45868 (9) | 0.3060 (3) | 0.0468 (5) | |
H4A | 0.055 (3) | 0.4604 (13) | 0.221 (5) | 0.077 (11)* | |
H4B | 0.077 (3) | 0.4630 (13) | 0.416 (5) | 0.075 (10)* | |
H4C | −0.041 (3) | 0.4833 (12) | 0.298 (4) | 0.061 (8)* | |
N5 | −0.1383 (2) | 0.33234 (9) | 0.6331 (3) | 0.0502 (5) | |
H5N | −0.064 (3) | 0.3330 (12) | 0.703 (4) | 0.066 (9)* | |
C7 | −0.0328 (2) | 0.40798 (11) | 0.3023 (3) | 0.0475 (6) | |
H7A | 0.031 (3) | 0.3801 (12) | 0.302 (4) | 0.064 (9)* | |
H7B | −0.101 (3) | 0.4031 (13) | 0.194 (5) | 0.079 (10)* | |
C8 | −0.0813 (2) | 0.40039 (10) | 0.4585 (3) | 0.0442 (5) | |
H8A | −0.014 (2) | 0.4046 (10) | 0.555 (3) | 0.044 (7)* | |
H8B | −0.145 (3) | 0.4247 (12) | 0.465 (4) | 0.063 (9)* | |
C9 | −0.1301 (3) | 0.34806 (11) | 0.4582 (4) | 0.0519 (6) | |
H9B | −0.211 (3) | 0.3458 (12) | 0.388 (4) | 0.070 (9)* | |
H9A | −0.080 (3) | 0.3243 (12) | 0.424 (4) | 0.064 (9)* | |
C10 | −0.2198 (4) | 0.36402 (16) | 0.7022 (6) | 0.0921 (13) | |
H10A | −0.2217 | 0.3524 | 0.8140 | 0.138* | |
H10B | −0.3006 | 0.3628 | 0.6274 | 0.138* | |
H10C | −0.1904 | 0.3975 | 0.7105 | 0.138* | |
C11 | −0.1745 (3) | 0.27941 (12) | 0.6313 (5) | 0.0770 (10) | |
H11A | −0.1794 | 0.2698 | 0.7440 | 0.116* | |
H11B | −0.1149 | 0.2593 | 0.5971 | 0.116* | |
H11C | −0.2527 | 0.2749 | 0.5517 | 0.116* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0418 (11) | 0.135 (2) | 0.0796 (15) | 0.0088 (13) | −0.0059 (10) | 0.0460 (16) |
O2A | 0.0568 (14) | 0.182 (3) | 0.0716 (16) | 0.0149 (17) | 0.0067 (12) | 0.0114 (18) |
O3A | 0.0842 (19) | 0.152 (3) | 0.105 (2) | −0.0082 (18) | 0.0149 (16) | 0.065 (2) |
O4A | 0.0751 (16) | 0.106 (2) | 0.0825 (17) | −0.0009 (14) | −0.0299 (13) | 0.0278 (15) |
O5A | 0.0464 (12) | 0.0848 (16) | 0.0938 (17) | 0.0102 (11) | −0.0076 (11) | −0.0147 (13) |
O6A | 0.101 (2) | 0.160 (3) | 0.0737 (17) | 0.036 (2) | 0.0250 (16) | 0.0044 (18) |
O7A | 0.0771 (16) | 0.0925 (18) | 0.0705 (15) | 0.0075 (13) | −0.0039 (12) | 0.0215 (13) |
N1A | 0.0559 (14) | 0.0654 (16) | 0.0673 (16) | −0.0051 (12) | 0.0001 (12) | 0.0078 (13) |
N2A | 0.0551 (15) | 0.0509 (14) | 0.0698 (17) | 0.0073 (11) | −0.0190 (12) | −0.0026 (12) |
N3A | 0.0634 (15) | 0.0694 (16) | 0.0506 (14) | 0.0064 (13) | −0.0013 (12) | −0.0007 (12) |
C1A | 0.0434 (13) | 0.0490 (14) | 0.0594 (16) | 0.0031 (11) | −0.0056 (11) | 0.0064 (12) |
C2A | 0.0486 (14) | 0.0425 (13) | 0.0574 (15) | 0.0007 (11) | −0.0002 (12) | 0.0015 (11) |
C3A | 0.0567 (16) | 0.0434 (14) | 0.0510 (16) | 0.0011 (12) | −0.0086 (13) | 0.0023 (12) |
C4A | 0.0456 (14) | 0.0390 (13) | 0.0582 (15) | 0.0065 (10) | −0.0123 (12) | −0.0045 (11) |
C5A | 0.0450 (14) | 0.0407 (13) | 0.0584 (16) | 0.0059 (11) | −0.0028 (12) | −0.0101 (11) |
C6A | 0.0481 (14) | 0.0414 (13) | 0.0518 (14) | 0.0022 (11) | −0.0023 (11) | −0.0030 (11) |
O1B | 0.0329 (8) | 0.0575 (10) | 0.0405 (8) | 0.0053 (7) | 0.0048 (6) | 0.0045 (7) |
O2B | 0.0717 (14) | 0.124 (2) | 0.0858 (16) | 0.0550 (15) | 0.0484 (13) | 0.0553 (15) |
O3B | 0.0667 (12) | 0.0717 (13) | 0.0526 (11) | 0.0058 (10) | 0.0278 (9) | 0.0205 (10) |
O4B | 0.0618 (12) | 0.0942 (16) | 0.0419 (10) | 0.0262 (11) | −0.0077 (9) | 0.0028 (10) |
O5B | 0.0390 (10) | 0.113 (2) | 0.0719 (14) | 0.0190 (11) | 0.0083 (10) | 0.0066 (13) |
O6B | 0.0550 (11) | 0.0910 (15) | 0.0414 (9) | −0.0020 (10) | 0.0200 (8) | −0.0054 (10) |
O7B | 0.0542 (11) | 0.0928 (15) | 0.0501 (11) | 0.0076 (11) | 0.0093 (9) | 0.0342 (11) |
N1B | 0.0459 (11) | 0.0522 (12) | 0.0462 (11) | 0.0075 (9) | 0.0186 (9) | 0.0081 (9) |
N2B | 0.0425 (11) | 0.0506 (12) | 0.0450 (12) | 0.0132 (9) | −0.0028 (9) | −0.0045 (9) |
N3B | 0.0392 (10) | 0.0615 (13) | 0.0336 (10) | −0.0061 (9) | 0.0077 (8) | 0.0057 (9) |
C1B | 0.0344 (10) | 0.0333 (10) | 0.0340 (10) | 0.0024 (8) | 0.0066 (8) | 0.0024 (8) |
C2B | 0.0385 (11) | 0.0382 (11) | 0.0339 (11) | 0.0044 (9) | 0.0121 (9) | 0.0015 (9) |
C3B | 0.0458 (12) | 0.0346 (11) | 0.0303 (11) | 0.0062 (9) | 0.0056 (9) | 0.0001 (8) |
C4B | 0.0356 (11) | 0.0354 (11) | 0.0363 (11) | 0.0073 (9) | 0.0006 (9) | −0.0034 (9) |
C5B | 0.0324 (10) | 0.0403 (11) | 0.0369 (11) | 0.0003 (9) | 0.0086 (9) | −0.0026 (9) |
C6B | 0.0362 (11) | 0.0423 (12) | 0.0302 (10) | −0.0020 (9) | 0.0077 (8) | 0.0026 (9) |
N4 | 0.0393 (11) | 0.0612 (14) | 0.0411 (11) | 0.0079 (10) | 0.0127 (9) | 0.0079 (10) |
N5 | 0.0419 (11) | 0.0514 (12) | 0.0524 (12) | −0.0031 (9) | 0.0030 (10) | 0.0066 (10) |
C7 | 0.0411 (12) | 0.0586 (16) | 0.0392 (12) | 0.0063 (11) | 0.0035 (10) | 0.0011 (11) |
C8 | 0.0387 (12) | 0.0482 (14) | 0.0419 (12) | 0.0018 (10) | 0.0034 (10) | 0.0034 (10) |
C9 | 0.0464 (14) | 0.0536 (16) | 0.0462 (14) | −0.0056 (12) | −0.0053 (11) | 0.0031 (12) |
C10 | 0.091 (3) | 0.093 (3) | 0.111 (3) | 0.024 (2) | 0.061 (2) | 0.024 (2) |
C11 | 0.079 (2) | 0.0607 (19) | 0.077 (2) | −0.0209 (16) | −0.0054 (17) | 0.0179 (16) |
O1A—C1A | 1.238 (3) | C1B—C2B | 1.445 (3) |
O2A—N1A | 1.209 (3) | C2B—C3B | 1.376 (3) |
O3A—N1A | 1.206 (4) | C3B—C4B | 1.374 (3) |
O4A—N2A | 1.218 (4) | C3B—H3B | 0.90 (3) |
O5A—N2A | 1.233 (4) | C4B—C5B | 1.389 (3) |
O6A—N3A | 1.213 (4) | C5B—C6B | 1.370 (3) |
O7A—N3A | 1.222 (3) | C5B—H5B | 0.89 (2) |
N1A—C2A | 1.454 (4) | N4—C7 | 1.490 (4) |
N2A—C4A | 1.449 (3) | N4—H4A | 0.88 (4) |
N3A—C6A | 1.458 (4) | N4—H4B | 0.96 (4) |
C1A—C2A | 1.448 (4) | N4—H4C | 0.95 (3) |
C1A—C6A | 1.448 (4) | N5—C10 | 1.468 (4) |
C2A—C3A | 1.383 (4) | N5—C11 | 1.484 (4) |
C3A—C4A | 1.363 (4) | N5—C9 | 1.499 (4) |
C3A—H3A | 0.83 (3) | N5—H5N | 0.88 (3) |
C4A—C5A | 1.382 (4) | C7—C8 | 1.511 (4) |
C5A—C6A | 1.364 (4) | C7—H7A | 1.05 (3) |
C5A—H5A | 0.96 (3) | C7—H7B | 1.02 (4) |
O1B—C1B | 1.253 (3) | C8—C9 | 1.516 (4) |
O2B—N1B | 1.203 (3) | C8—H8A | 0.94 (3) |
O3B—N1B | 1.219 (3) | C8—H8B | 0.98 (3) |
O4B—N2B | 1.215 (3) | C9—H9B | 0.95 (4) |
O5B—N2B | 1.226 (3) | C9—H9A | 0.94 (3) |
O6B—N3B | 1.219 (3) | C10—H10A | 0.9600 |
O7B—N3B | 1.223 (3) | C10—H10B | 0.9600 |
N1B—C2B | 1.455 (3) | C10—H10C | 0.9600 |
N2B—C4B | 1.447 (3) | C11—H11A | 0.9600 |
N3B—C6B | 1.462 (3) | C11—H11B | 0.9600 |
C1B—C6B | 1.441 (3) | C11—H11C | 0.9600 |
O3A—N1A—O2A | 120.7 (3) | C6B—C5B—C4B | 119.0 (2) |
O3A—N1A—C2A | 119.4 (3) | C6B—C5B—H5B | 121.4 (15) |
O2A—N1A—C2A | 119.8 (3) | C4B—C5B—H5B | 119.5 (15) |
O4A—N2A—O5A | 123.2 (3) | C5B—C6B—C1B | 124.70 (19) |
O4A—N2A—C4A | 118.4 (3) | C5B—C6B—N3B | 115.47 (19) |
O5A—N2A—C4A | 118.4 (3) | C1B—C6B—N3B | 119.83 (19) |
O6A—N3A—O7A | 122.5 (3) | C7—N4—H4A | 107 (2) |
O6A—N3A—C6A | 118.2 (3) | C7—N4—H4B | 108 (2) |
O7A—N3A—C6A | 119.1 (3) | H4A—N4—H4B | 112 (3) |
O1A—C1A—C2A | 125.6 (3) | C7—N4—H4C | 110.8 (18) |
O1A—C1A—C6A | 122.1 (3) | H4A—N4—H4C | 113 (3) |
C2A—C1A—C6A | 112.2 (2) | H4B—N4—H4C | 106 (3) |
C3A—C2A—C1A | 122.9 (3) | C10—N5—C11 | 111.3 (3) |
C3A—C2A—N1A | 117.0 (3) | C10—N5—C9 | 112.9 (2) |
C1A—C2A—N1A | 120.1 (2) | C11—N5—C9 | 110.2 (2) |
C4A—C3A—C2A | 119.9 (3) | C10—N5—H5N | 110 (2) |
C4A—C3A—H3A | 128 (2) | C11—N5—H5N | 104 (2) |
C2A—C3A—H3A | 112 (2) | C9—N5—H5N | 108 (2) |
C3A—C4A—C5A | 121.6 (2) | N4—C7—C8 | 109.7 (2) |
C3A—C4A—N2A | 120.4 (3) | N4—C7—H7A | 112.5 (17) |
C5A—C4A—N2A | 118.1 (3) | C8—C7—H7A | 107.8 (16) |
C6A—C5A—C4A | 118.8 (3) | N4—C7—H7B | 110 (2) |
C6A—C5A—H5A | 119.0 (17) | C8—C7—H7B | 110.0 (19) |
C4A—C5A—H5A | 122.2 (17) | H7A—C7—H7B | 106 (3) |
C5A—C6A—C1A | 124.5 (3) | C7—C8—C9 | 109.6 (2) |
C5A—C6A—N3A | 115.8 (3) | C7—C8—H8A | 106.4 (15) |
C1A—C6A—N3A | 119.7 (2) | C9—C8—H8A | 109.4 (16) |
O2B—N1B—O3B | 121.5 (2) | C7—C8—H8B | 112.3 (18) |
O2B—N1B—C2B | 120.2 (2) | C9—C8—H8B | 110.4 (18) |
O3B—N1B—C2B | 118.2 (2) | H8A—C8—H8B | 109 (2) |
O4B—N2B—O5B | 123.4 (2) | N5—C9—C8 | 111.8 (2) |
O4B—N2B—C4B | 118.3 (2) | N5—C9—H9B | 105 (2) |
O5B—N2B—C4B | 118.2 (2) | C8—C9—H9B | 111 (2) |
O6B—N3B—O7B | 123.2 (2) | N5—C9—H9A | 106 (2) |
O6B—N3B—C6B | 117.6 (2) | C8—C9—H9A | 113 (2) |
O7B—N3B—C6B | 119.2 (2) | H9B—C9—H9A | 110 (3) |
O1B—C1B—C6B | 124.48 (19) | N5—C10—H10A | 109.5 |
O1B—C1B—C2B | 124.1 (2) | N5—C10—H10B | 109.5 |
C6B—C1B—C2B | 111.36 (18) | H10A—C10—H10B | 109.5 |
C3B—C2B—C1B | 124.9 (2) | N5—C10—H10C | 109.5 |
C3B—C2B—N1B | 115.40 (19) | H10A—C10—H10C | 109.5 |
C1B—C2B—N1B | 119.72 (19) | H10B—C10—H10C | 109.5 |
C4B—C3B—C2B | 118.8 (2) | N5—C11—H11A | 109.5 |
C4B—C3B—H3B | 122 (2) | N5—C11—H11B | 109.5 |
C2B—C3B—H3B | 119 (2) | H11A—C11—H11B | 109.5 |
C3B—C4B—C5B | 121.1 (2) | N5—C11—H11C | 109.5 |
C3B—C4B—N2B | 119.3 (2) | H11A—C11—H11C | 109.5 |
C5B—C4B—N2B | 119.5 (2) | H11B—C11—H11C | 109.5 |
O1A—C1A—C2A—C3A | −179.3 (3) | O1B—C1B—C2B—N1B | −0.5 (3) |
C6A—C1A—C2A—C3A | 2.1 (4) | C6B—C1B—C2B—N1B | −177.6 (2) |
O1A—C1A—C2A—N1A | −0.5 (5) | O2B—N1B—C2B—C3B | 150.7 (3) |
C6A—C1A—C2A—N1A | −179.1 (2) | O3B—N1B—C2B—C3B | −27.2 (3) |
O3A—N1A—C2A—C3A | −9.0 (4) | O2B—N1B—C2B—C1B | −29.8 (4) |
O2A—N1A—C2A—C3A | 168.2 (3) | O3B—N1B—C2B—C1B | 152.3 (2) |
O3A—N1A—C2A—C1A | 172.1 (3) | C1B—C2B—C3B—C4B | 0.1 (4) |
O2A—N1A—C2A—C1A | −10.6 (4) | N1B—C2B—C3B—C4B | 179.5 (2) |
C1A—C2A—C3A—C4A | −1.1 (4) | C2B—C3B—C4B—C5B | −2.2 (3) |
N1A—C2A—C3A—C4A | −180.0 (2) | C2B—C3B—C4B—N2B | 177.0 (2) |
C2A—C3A—C4A—C5A | −1.4 (4) | O4B—N2B—C4B—C3B | −0.1 (3) |
C2A—C3A—C4A—N2A | 178.5 (2) | O5B—N2B—C4B—C3B | −178.7 (2) |
O4A—N2A—C4A—C3A | 9.0 (4) | O4B—N2B—C4B—C5B | 179.1 (2) |
O5A—N2A—C4A—C3A | −171.1 (3) | O5B—N2B—C4B—C5B | 0.5 (3) |
O4A—N2A—C4A—C5A | −171.1 (3) | C3B—C4B—C5B—C6B | 2.1 (3) |
O5A—N2A—C4A—C5A | 8.7 (4) | N2B—C4B—C5B—C6B | −177.1 (2) |
C3A—C4A—C5A—C6A | 2.7 (4) | C4B—C5B—C6B—C1B | 0.1 (3) |
N2A—C4A—C5A—C6A | −177.1 (2) | C4B—C5B—C6B—N3B | −179.3 (2) |
C4A—C5A—C6A—C1A | −1.7 (4) | O1B—C1B—C6B—C5B | −179.0 (2) |
C4A—C5A—C6A—N3A | 178.9 (2) | C2B—C1B—C6B—C5B | −1.9 (3) |
O1A—C1A—C6A—C5A | −179.4 (3) | O1B—C1B—C6B—N3B | 0.4 (3) |
C2A—C1A—C6A—C5A | −0.7 (4) | C2B—C1B—C6B—N3B | 177.5 (2) |
O1A—C1A—C6A—N3A | 0.0 (4) | O6B—N3B—C6B—C5B | 27.0 (3) |
C2A—C1A—C6A—N3A | 178.8 (2) | O7B—N3B—C6B—C5B | −151.9 (2) |
O6A—N3A—C6A—C5A | 27.4 (4) | O6B—N3B—C6B—C1B | −152.4 (2) |
O7A—N3A—C6A—C5A | −147.2 (3) | O7B—N3B—C6B—C1B | 28.6 (3) |
O6A—N3A—C6A—C1A | −152.1 (3) | N4—C7—C8—C9 | −177.6 (2) |
O7A—N3A—C6A—C1A | 33.3 (4) | C10—N5—C9—C8 | 60.5 (3) |
O1B—C1B—C2B—C3B | 178.9 (2) | C11—N5—C9—C8 | −174.4 (2) |
C6B—C1B—C2B—C3B | 1.8 (3) | C7—C8—C9—N5 | 159.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5N···O1A | 0.88 (3) | 1.89 (3) | 2.655 (3) | 143 (3) |
N5—H5N···O2A | 0.88 (3) | 2.26 (3) | 2.968 (3) | 137 (3) |
N4—H4A···O2B | 0.88 (4) | 2.33 (4) | 3.188 (3) | 166 (3) |
N4—H4A···O3B | 0.88 (4) | 2.31 (4) | 3.023 (3) | 138 (3) |
N4—H4B···O1Bi | 0.96 (4) | 1.90 (4) | 2.846 (3) | 167 (3) |
N4—H4B···O7Bi | 0.96 (4) | 2.53 (3) | 3.089 (3) | 118 (3) |
N4—H4C···O1Bii | 0.95 (3) | 1.89 (3) | 2.814 (3) | 164 (3) |
N4—H4C···O2Bii | 0.95 (3) | 2.34 (3) | 2.905 (3) | 117 (2) |
C7—H7A···O7A | 1.05 (3) | 2.48 (3) | 3.243 (4) | 129 (2) |
C8—H8A···O1A | 0.94 (3) | 2.52 (3) | 3.117 (3) | 122 (2) |
C8—H8A···O1Bi | 0.94 (3) | 2.66 (3) | 3.384 (3) | 135 (2) |
C3B—H3B···O6Bi | 0.90 (3) | 2.49 (3) | 3.290 (3) | 148 (3) |
C3A—H3A···O6Ai | 0.83 (3) | 2.65 (3) | 3.385 (4) | 147 (3) |
C7—H7B···O5Biii | 1.02 (4) | 2.48 (4) | 3.419 (3) | 153 (3) |
C11—H11C···O4Aiv | 0.96 | 2.55 | 3.469 (4) | 161 |
Symmetry codes: (i) x, y, z+1; (ii) −x, −y+1, −z; (iii) x−1, y, z; (iv) x−1, y, z−1. |