| Literature DB >> 21201371 |
Hua Sun1, Chun-Xia Ren, Bin Shen, Zhi-Qiang Liu, Yu-Qiang Ding.
Abstract
The reaction of 1,4-bis-(4,5-dihydro-1H-imidazol-2-yl)benzene (bib) with silver(I) nitrate in a 1:1 molar ratio generates the metallacyclic title complex, [Ag(2)(C(12)H(14)N(4))(2)](NO(3))(2)·2H(2)O, in which the bib ligand displays a cis configuration. Each bib ligand acts as a bidentate bridging ligand connecting a pair of Ag(I) ions to form a [2 + 2] metallamacrocycle in which the Ag⋯Ag distance is 6.77 (2) Å. Each Ag(I) ion has weak contacts (2.91 Å) with the nitrate anion. The uncoordinated water mol-ecules make hydrogen bonds with nitrate O atoms, forming chains. The H atoms attached to the uncoordinated nitro-gen inter-act with these chains through N-H⋯O hydrogen bonds, forming layers parallel to the (11) plane.Entities:
Year: 2008 PMID: 21201371 PMCID: PMC2960425 DOI: 10.1107/S1600536808001633
Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN: 1600-5368
| [Ag2(C12H14N4)2](NO3)2·2H2O | |
| Triclinic, | |
| Hall symbol: -P 1 | Mo |
| Cell parameters from 2137 reflections | |
| θ = 2.5–23.9º | |
| µ = 1.40 mm−1 | |
| α = 97.496 (3)º | |
| β = 95.354 (3)º | Block, colourless |
| γ = 101.613 (3)º | 0.30 × 0.25 × 0.20 mm |
| Bruker SMART CCD area-detector diffractometer | 5316 independent reflections |
| Radiation source: fine-focus sealed tube | 3797 reflections with |
| Monochromator: graphite | |
| θmax = 25.5º | |
| φ and ω scans | θmin = 1.9º |
| Absorption correction: multi-scan(SADABS; Bruker, 1998) | |
| 7650 measured reflections |
| Refinement on | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| H-atom parameters constrained | |
| | |
| (Δ/σ)max = 0.001 | |
| 5316 reflections | Δρmax = 2.17 e Å−3 |
| 397 parameters | Δρmin = −0.82 e Å−3 |
| 3 restraints | Extinction correction: none |
| Primary atom site location: structure-invariant direct methods |
| 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 |
| Ag1 | 0.72496 (4) | 0.29100 (4) | 0.19588 (3) | 0.04584 (17) | |
| Ag2 | 1.24475 (4) | 0.78014 (4) | 0.21805 (3) | 0.04782 (17) | |
| N1 | 0.5471 (5) | 0.3689 (5) | −0.0866 (4) | 0.0556 (13) | |
| H1 | 0.5461 | 0.4098 | −0.1374 | 0.067* | |
| N2 | 0.6169 (4) | 0.3282 (4) | 0.0656 (3) | 0.0444 (11) | |
| N3 | 1.0950 (5) | 0.8764 (5) | −0.0663 (4) | 0.0562 (13) | |
| H3 | 1.0437 | 0.8590 | −0.1234 | 0.067* | |
| N4 | 1.1847 (4) | 0.8423 (4) | 0.0829 (3) | 0.0446 (11) | |
| N5 | 0.7991 (4) | 0.2146 (4) | 0.3188 (3) | 0.0425 (10) | |
| N6 | 0.9176 (5) | 0.1613 (4) | 0.4484 (3) | 0.0487 (12) | |
| H6 | 0.9871 | 0.1636 | 0.4901 | 0.058* | |
| N7 | 1.3532 (4) | 0.7500 (4) | 0.3484 (3) | 0.0443 (11) | |
| N8 | 1.4423 (4) | 0.6791 (4) | 0.4819 (4) | 0.0510 (12) | |
| H8 | 1.4496 | 0.6282 | 0.5248 | 0.061* | |
| C1 | 0.4473 (5) | 0.2619 (6) | −0.0755 (4) | 0.0510 (14) | |
| H1A | 0.4548 | 0.1880 | −0.1209 | 0.061* | |
| H1B | 0.3586 | 0.2768 | −0.0886 | 0.061* | |
| C2 | 0.4810 (6) | 0.2495 (6) | 0.0358 (4) | 0.0542 (15) | |
| H2A | 0.4184 | 0.2796 | 0.0775 | 0.065* | |
| H2B | 0.4796 | 0.1632 | 0.0433 | 0.065* | |
| C3 | 0.6420 (5) | 0.3957 (5) | −0.0059 (4) | 0.0389 (12) | |
| C4 | 0.7598 (5) | 0.4977 (5) | −0.0017 (4) | 0.0373 (11) | |
| C5 | 0.7993 (5) | 0.5387 (5) | −0.0918 (4) | 0.0458 (13) | |
| H5 | 0.7540 | 0.4984 | −0.1549 | 0.055* | |
| C6 | 0.9054 (5) | 0.6390 (5) | −0.0876 (4) | 0.0478 (14) | |
| H6A | 0.9299 | 0.6661 | −0.1479 | 0.057* | |
| C7 | 0.9754 (5) | 0.6992 (5) | 0.0054 (4) | 0.0385 (12) | |
| C8 | 0.9353 (5) | 0.6586 (5) | 0.0946 (4) | 0.0449 (13) | |
| H8A | 0.9803 | 0.6992 | 0.1576 | 0.054* | |
| C9 | 0.8298 (5) | 0.5590 (5) | 0.0907 (4) | 0.0430 (12) | |
| H9 | 0.8053 | 0.5327 | 0.1512 | 0.052* | |
| C10 | 1.0863 (5) | 0.8076 (5) | 0.0097 (4) | 0.0391 (12) | |
| C11 | 1.2038 (6) | 0.9842 (6) | −0.0381 (5) | 0.0585 (16) | |
| H11A | 1.1718 | 1.0604 | −0.0223 | 0.070* | |
| H11B | 1.2607 | 0.9934 | −0.0918 | 0.070* | |
| C12 | 1.2758 (6) | 0.9513 (5) | 0.0572 (4) | 0.0529 (15) | |
| H12A | 1.3596 | 0.9307 | 0.0428 | 0.064* | |
| H12B | 1.2929 | 1.0206 | 0.1130 | 0.064* | |
| C13 | 0.7201 (6) | 0.0958 (5) | 0.3396 (4) | 0.0517 (14) | |
| H13A | 0.7169 | 0.0290 | 0.2837 | 0.062* | |
| H13B | 0.6301 | 0.1034 | 0.3487 | 0.062* | |
| C14 | 0.7918 (6) | 0.0695 (5) | 0.4389 (4) | 0.0488 (14) | |
| H14A | 0.7433 | 0.0841 | 0.4968 | 0.059* | |
| H14B | 0.8055 | −0.0153 | 0.4319 | 0.059* | |
| C15 | 0.9071 (5) | 0.2413 (5) | 0.3818 (4) | 0.0407 (12) | |
| C16 | 1.0166 (5) | 0.3512 (5) | 0.3846 (4) | 0.0379 (11) | |
| C17 | 0.9944 (5) | 0.4653 (5) | 0.3636 (4) | 0.0404 (12) | |
| H17 | 0.9080 | 0.4733 | 0.3454 | 0.048* | |
| C18 | 1.0980 (5) | 0.5674 (4) | 0.3691 (4) | 0.0349 (11) | |
| H18 | 1.0814 | 0.6428 | 0.3532 | 0.042* | |
| C19 | 1.2278 (5) | 0.5569 (5) | 0.3987 (4) | 0.0380 (12) | |
| C20 | 1.2499 (5) | 0.4421 (5) | 0.4183 (4) | 0.0422 (12) | |
| H20 | 1.3363 | 0.4335 | 0.4360 | 0.051* | |
| C21 | 1.1465 (5) | 0.3411 (5) | 0.4119 (4) | 0.0413 (12) | |
| H21 | 1.1633 | 0.2651 | 0.4260 | 0.050* | |
| C22 | 1.3392 (5) | 0.6637 (5) | 0.4076 (4) | 0.0359 (11) | |
| C23 | 1.4810 (6) | 0.8388 (6) | 0.3862 (5) | 0.0539 (15) | |
| H23A | 1.4667 | 0.9226 | 0.4044 | 0.065* | |
| H23B | 1.5407 | 0.8402 | 0.3340 | 0.065* | |
| C24 | 1.5388 (5) | 0.7930 (5) | 0.4794 (4) | 0.0530 (14) | |
| H24A | 1.6260 | 0.7763 | 0.4711 | 0.064* | |
| H24B | 1.5450 | 0.8528 | 0.5409 | 0.064* | |
| N9 | 0.9177 (6) | 0.9780 (5) | −0.2608 (4) | 0.0576 (13) | |
| O1 | 0.8766 (5) | 0.8843 (4) | −0.2188 (4) | 0.0705 (13) | |
| O2 | 1.0326 (5) | 1.0387 (4) | −0.2346 (4) | 0.0724 (13) | |
| O3 | 0.8422 (6) | 1.0092 (5) | −0.3252 (4) | 0.0875 (16) | |
| N10 | 0.4137 (5) | 0.4736 (5) | −0.2932 (3) | 0.0514 (12) | |
| O4 | 0.3505 (5) | 0.5295 (5) | −0.3486 (3) | 0.0719 (13) | |
| O5 | 0.3607 (4) | 0.3683 (5) | −0.2766 (3) | 0.0703 (13) | |
| O6 | 0.5283 (4) | 0.5234 (4) | −0.2531 (3) | 0.0635 (12) | |
| O1W | 1.1003 (4) | 0.2239 (4) | 0.6372 (3) | 0.0721 (13) | |
| H11W | 1.0637 | 0.1943 | 0.6860 | 0.108* | |
| H12W | 1.1775 | 0.2658 | 0.6616 | 0.108* | |
| O2W | 0.5808 (5) | 0.7918 (5) | −0.2779 (4) | 0.0920 (16) | |
| H21W | 0.6639 | 0.8127 | −0.2803 | 0.138* | |
| H22W | 0.5669 | 0.7283 | −0.2473 | 0.138* |
| Ag1 | 0.0469 (3) | 0.0491 (3) | 0.0405 (3) | 0.0061 (2) | −0.00367 (19) | 0.01590 (19) |
| Ag2 | 0.0504 (3) | 0.0478 (3) | 0.0440 (3) | 0.0056 (2) | −0.00285 (19) | 0.0163 (2) |
| N1 | 0.051 (3) | 0.065 (3) | 0.045 (3) | −0.005 (2) | −0.012 (2) | 0.024 (2) |
| N2 | 0.044 (3) | 0.051 (3) | 0.036 (2) | 0.005 (2) | −0.0003 (19) | 0.014 (2) |
| N3 | 0.059 (3) | 0.062 (3) | 0.043 (3) | 0.000 (3) | −0.007 (2) | 0.024 (2) |
| N4 | 0.049 (3) | 0.041 (3) | 0.040 (2) | 0.001 (2) | 0.000 (2) | 0.010 (2) |
| N5 | 0.039 (2) | 0.044 (3) | 0.042 (2) | 0.004 (2) | −0.004 (2) | 0.012 (2) |
| N6 | 0.049 (3) | 0.050 (3) | 0.046 (3) | 0.007 (2) | −0.007 (2) | 0.020 (2) |
| N7 | 0.042 (3) | 0.044 (3) | 0.044 (2) | 0.005 (2) | −0.005 (2) | 0.011 (2) |
| N8 | 0.043 (3) | 0.052 (3) | 0.055 (3) | −0.002 (2) | −0.010 (2) | 0.023 (2) |
| C1 | 0.045 (3) | 0.059 (4) | 0.046 (3) | 0.005 (3) | −0.006 (3) | 0.015 (3) |
| C2 | 0.049 (3) | 0.060 (4) | 0.051 (3) | 0.002 (3) | −0.002 (3) | 0.019 (3) |
| C3 | 0.039 (3) | 0.047 (3) | 0.031 (3) | 0.012 (2) | −0.002 (2) | 0.007 (2) |
| C4 | 0.040 (3) | 0.041 (3) | 0.034 (3) | 0.013 (2) | 0.004 (2) | 0.012 (2) |
| C5 | 0.052 (3) | 0.047 (3) | 0.034 (3) | 0.003 (3) | −0.001 (2) | 0.008 (2) |
| C6 | 0.053 (3) | 0.058 (4) | 0.033 (3) | 0.009 (3) | 0.006 (2) | 0.017 (3) |
| C7 | 0.039 (3) | 0.042 (3) | 0.036 (3) | 0.012 (2) | −0.002 (2) | 0.009 (2) |
| C8 | 0.045 (3) | 0.053 (3) | 0.034 (3) | 0.006 (3) | −0.004 (2) | 0.013 (2) |
| C9 | 0.044 (3) | 0.053 (3) | 0.032 (3) | 0.003 (3) | 0.002 (2) | 0.016 (2) |
| C10 | 0.044 (3) | 0.040 (3) | 0.036 (3) | 0.010 (2) | 0.007 (2) | 0.012 (2) |
| C11 | 0.058 (4) | 0.057 (4) | 0.058 (4) | −0.002 (3) | 0.004 (3) | 0.025 (3) |
| C12 | 0.052 (4) | 0.051 (3) | 0.051 (3) | −0.003 (3) | 0.008 (3) | 0.015 (3) |
| C13 | 0.045 (3) | 0.052 (3) | 0.055 (4) | −0.001 (3) | −0.002 (3) | 0.022 (3) |
| C14 | 0.052 (3) | 0.049 (3) | 0.047 (3) | 0.004 (3) | 0.008 (3) | 0.019 (3) |
| C15 | 0.041 (3) | 0.041 (3) | 0.042 (3) | 0.008 (2) | 0.004 (2) | 0.015 (2) |
| C16 | 0.039 (3) | 0.041 (3) | 0.034 (3) | 0.007 (2) | 0.001 (2) | 0.011 (2) |
| C17 | 0.040 (3) | 0.046 (3) | 0.039 (3) | 0.016 (2) | 0.004 (2) | 0.012 (2) |
| C18 | 0.038 (3) | 0.027 (2) | 0.040 (3) | 0.007 (2) | 0.001 (2) | 0.010 (2) |
| C19 | 0.041 (3) | 0.043 (3) | 0.031 (3) | 0.009 (2) | 0.004 (2) | 0.009 (2) |
| C20 | 0.036 (3) | 0.045 (3) | 0.050 (3) | 0.012 (2) | 0.004 (2) | 0.017 (2) |
| C21 | 0.040 (3) | 0.037 (3) | 0.048 (3) | 0.009 (2) | 0.000 (2) | 0.014 (2) |
| C22 | 0.034 (3) | 0.040 (3) | 0.038 (3) | 0.012 (2) | 0.005 (2) | 0.014 (2) |
| C23 | 0.045 (3) | 0.047 (3) | 0.063 (4) | −0.006 (3) | 0.002 (3) | 0.013 (3) |
| C24 | 0.043 (3) | 0.057 (4) | 0.052 (3) | −0.001 (3) | −0.007 (3) | 0.013 (3) |
| N9 | 0.073 (4) | 0.060 (3) | 0.045 (3) | 0.027 (3) | 0.003 (3) | 0.010 (3) |
| O1 | 0.076 (3) | 0.061 (3) | 0.073 (3) | 0.010 (2) | −0.001 (2) | 0.020 (2) |
| O2 | 0.080 (4) | 0.068 (3) | 0.070 (3) | 0.010 (3) | 0.006 (3) | 0.024 (3) |
| O3 | 0.103 (4) | 0.096 (4) | 0.069 (3) | 0.042 (3) | −0.018 (3) | 0.025 (3) |
| N10 | 0.049 (3) | 0.069 (4) | 0.038 (3) | 0.017 (3) | 0.003 (2) | 0.013 (2) |
| O4 | 0.069 (3) | 0.090 (4) | 0.062 (3) | 0.029 (3) | −0.009 (2) | 0.026 (3) |
| O5 | 0.063 (3) | 0.078 (3) | 0.066 (3) | 0.004 (3) | −0.002 (2) | 0.026 (3) |
| O6 | 0.047 (3) | 0.077 (3) | 0.062 (3) | 0.005 (2) | −0.004 (2) | 0.015 (2) |
| O1W | 0.068 (3) | 0.077 (3) | 0.067 (3) | 0.004 (2) | −0.015 (2) | 0.031 (3) |
| O2W | 0.079 (3) | 0.127 (5) | 0.071 (3) | 0.016 (3) | 0.005 (3) | 0.027 (3) |
| Ag1—N5 | 2.087 (4) | C8—H8A | 0.9300 |
| Ag1—N2 | 2.104 (4) | C9—H9 | 0.9300 |
| Ag2—N7 | 2.076 (4) | C11—C12 | 1.530 (8) |
| Ag2—N4 | 2.089 (4) | C11—H11A | 0.9700 |
| N1—C3 | 1.344 (7) | C11—H11B | 0.9700 |
| N1—C1 | 1.439 (7) | C12—H12A | 0.9700 |
| N1—H1 | 0.8600 | C12—H12B | 0.9700 |
| N2—C3 | 1.296 (7) | C13—C14 | 1.542 (7) |
| N2—C2 | 1.486 (7) | C13—H13A | 0.9700 |
| N3—C10 | 1.339 (6) | C13—H13B | 0.9700 |
| N3—C11 | 1.447 (7) | C14—H14A | 0.9700 |
| N3—H3 | 0.8600 | C14—H14B | 0.9700 |
| N4—C10 | 1.300 (7) | C15—C16 | 1.480 (7) |
| N4—C12 | 1.473 (7) | C16—C17 | 1.385 (7) |
| N5—C15 | 1.291 (7) | C16—C21 | 1.390 (7) |
| N5—C13 | 1.474 (7) | C17—C18 | 1.381 (7) |
| N6—C15 | 1.343 (6) | C17—H17 | 0.9300 |
| N6—C14 | 1.466 (7) | C18—C19 | 1.397 (7) |
| N6—H6 | 0.8600 | C18—H18 | 0.9300 |
| N7—C22 | 1.308 (7) | C19—C20 | 1.386 (7) |
| N7—C23 | 1.480 (7) | C19—C22 | 1.459 (7) |
| N8—C22 | 1.352 (7) | C20—C21 | 1.371 (7) |
| N8—C24 | 1.447 (7) | C20—H20 | 0.9300 |
| N8—H8 | 0.8600 | C21—H21 | 0.9300 |
| C1—C2 | 1.517 (7) | C23—C24 | 1.515 (8) |
| C1—H1A | 0.9700 | C23—H23A | 0.9700 |
| C1—H1B | 0.9700 | C23—H23B | 0.9700 |
| C2—H2A | 0.9700 | C24—H24A | 0.9700 |
| C2—H2B | 0.9700 | C24—H24B | 0.9700 |
| C3—C4 | 1.475 (7) | N9—O3 | 1.234 (6) |
| C4—C9 | 1.382 (7) | N9—O2 | 1.236 (7) |
| C4—C5 | 1.402 (7) | N9—O1 | 1.258 (7) |
| C5—C6 | 1.386 (7) | N10—O5 | 1.239 (6) |
| C5—H5 | 0.9300 | N10—O6 | 1.240 (6) |
| C6—C7 | 1.385 (7) | N10—O4 | 1.243 (6) |
| C6—H6A | 0.9300 | O1W—H11W | 0.8499 |
| C7—C8 | 1.390 (7) | O1W—H12W | 0.8500 |
| C7—C10 | 1.475 (7) | O2W—H21W | 0.8500 |
| C8—C9 | 1.378 (7) | O2W—H22W | 0.8499 |
| N5—Ag1—N2 | 166.51 (18) | N3—C11—H11B | 111.5 |
| N7—Ag2—N4 | 164.37 (18) | C12—C11—H11B | 111.5 |
| C3—N1—C1 | 110.0 (5) | H11A—C11—H11B | 109.3 |
| C3—N1—H1 | 125.0 | N4—C12—C11 | 105.0 (5) |
| C1—N1—H1 | 125.0 | N4—C12—H12A | 110.8 |
| C3—N2—C2 | 107.1 (4) | C11—C12—H12A | 110.8 |
| C3—N2—Ag1 | 136.2 (4) | N4—C12—H12B | 110.8 |
| C2—N2—Ag1 | 116.2 (3) | C11—C12—H12B | 110.8 |
| C10—N3—C11 | 109.9 (5) | H12A—C12—H12B | 108.8 |
| C10—N3—H3 | 125.1 | N5—C13—C14 | 105.5 (4) |
| C11—N3—H3 | 125.1 | N5—C13—H13A | 110.6 |
| C10—N4—C12 | 107.7 (4) | C14—C13—H13A | 110.6 |
| C10—N4—Ag2 | 136.8 (4) | N5—C13—H13B | 110.6 |
| C12—N4—Ag2 | 115.5 (3) | C14—C13—H13B | 110.6 |
| C15—N5—C13 | 107.1 (4) | H13A—C13—H13B | 108.8 |
| C15—N5—Ag1 | 135.4 (4) | N6—C14—C13 | 100.8 (4) |
| C13—N5—Ag1 | 117.3 (3) | N6—C14—H14A | 111.6 |
| C15—N6—C14 | 109.1 (4) | C13—C14—H14A | 111.6 |
| C15—N6—H6 | 125.4 | N6—C14—H14B | 111.6 |
| C14—N6—H6 | 125.4 | C13—C14—H14B | 111.6 |
| C22—N7—C23 | 107.4 (4) | H14A—C14—H14B | 109.4 |
| C22—N7—Ag2 | 134.8 (4) | N5—C15—N6 | 115.9 (5) |
| C23—N7—Ag2 | 117.7 (4) | N5—C15—C16 | 124.9 (5) |
| C22—N8—C24 | 110.8 (4) | N6—C15—C16 | 119.2 (5) |
| C22—N8—H8 | 124.6 | C17—C16—C21 | 118.5 (5) |
| C24—N8—H8 | 124.6 | C17—C16—C15 | 122.4 (5) |
| N1—C1—C2 | 101.7 (4) | C21—C16—C15 | 119.1 (4) |
| N1—C1—H1A | 111.4 | C18—C17—C16 | 121.4 (5) |
| C2—C1—H1A | 111.4 | C18—C17—H17 | 119.3 |
| N1—C1—H1B | 111.4 | C16—C17—H17 | 119.3 |
| C2—C1—H1B | 111.4 | C17—C18—C19 | 119.6 (4) |
| H1A—C1—H1B | 109.3 | C17—C18—H18 | 120.2 |
| N2—C2—C1 | 104.6 (4) | C19—C18—H18 | 120.2 |
| N2—C2—H2A | 110.8 | C20—C19—C18 | 118.9 (5) |
| C1—C2—H2A | 110.8 | C20—C19—C22 | 120.1 (5) |
| N2—C2—H2B | 110.8 | C18—C19—C22 | 121.1 (4) |
| C1—C2—H2B | 110.8 | C21—C20—C19 | 121.0 (5) |
| H2A—C2—H2B | 108.9 | C21—C20—H20 | 119.5 |
| N2—C3—N1 | 114.1 (5) | C19—C20—H20 | 119.5 |
| N2—C3—C4 | 125.2 (5) | C20—C21—C16 | 120.6 (5) |
| N1—C3—C4 | 120.6 (5) | C20—C21—H21 | 119.7 |
| C9—C4—C5 | 118.3 (5) | C16—C21—H21 | 119.7 |
| C9—C4—C3 | 121.3 (4) | N7—C22—N8 | 113.6 (5) |
| C5—C4—C3 | 120.3 (5) | N7—C22—C19 | 126.5 (5) |
| C6—C5—C4 | 120.4 (5) | N8—C22—C19 | 119.9 (4) |
| C6—C5—H5 | 119.8 | N7—C23—C24 | 106.2 (4) |
| C4—C5—H5 | 119.8 | N7—C23—H23A | 110.5 |
| C7—C6—C5 | 120.7 (5) | C24—C23—H23A | 110.5 |
| C7—C6—H6A | 119.6 | N7—C23—H23B | 110.5 |
| C5—C6—H6A | 119.6 | C24—C23—H23B | 110.5 |
| C6—C7—C8 | 118.6 (5) | H23A—C23—H23B | 108.7 |
| C6—C7—C10 | 120.5 (5) | N8—C24—C23 | 101.8 (4) |
| C8—C7—C10 | 120.8 (5) | N8—C24—H24A | 111.4 |
| C9—C8—C7 | 120.8 (5) | C23—C24—H24A | 111.4 |
| C9—C8—H8A | 119.6 | N8—C24—H24B | 111.4 |
| C7—C8—H8A | 119.6 | C23—C24—H24B | 111.4 |
| C8—C9—C4 | 121.1 (5) | H24A—C24—H24B | 109.3 |
| C8—C9—H9 | 119.5 | O3—N9—O2 | 121.3 (6) |
| C4—C9—H9 | 119.5 | O3—N9—O1 | 119.7 (6) |
| N4—C10—N3 | 114.4 (5) | O2—N9—O1 | 118.9 (5) |
| N4—C10—C7 | 124.5 (5) | O5—N10—O6 | 120.0 (5) |
| N3—C10—C7 | 121.1 (5) | O5—N10—O4 | 119.6 (5) |
| N3—C11—C12 | 101.6 (4) | O6—N10—O4 | 120.4 (5) |
| N3—C11—H11A | 111.5 | H11W—O1W—H12W | 107.7 |
| C12—C11—H11A | 111.5 | H21W—O2W—H22W | 107.7 |
| H··· | ||||
| N1—H1···O6 | 0.86 | 2.12 | 2.980 (6) | 173 |
| N1—H1···O5 | 0.86 | 2.46 | 3.029 (6) | 124 |
| N3—H3···O1 | 0.86 | 2.13 | 2.915 (7) | 151 |
| N3—H3···O2 | 0.86 | 2.64 | 3.143 (6) | 119 |
| N6—H6···O1W | 0.86 | 2.13 | 2.912 (6) | 150 |
| N8—H8···O4i | 0.86 | 2.33 | 3.073 (7) | 145 |
| O1W—H11W···O2ii | 0.85 | 2.12 | 2.852 (6) | 144 |
| O1W—H12W···O5i | 0.85 | 2.04 | 2.888 (7) | 178 |
| O2W—H21W···O1 | 0.85 | 2.22 | 3.021 (7) | 157 |
| O2W—H22W···O6 | 0.85 | 2.21 | 2.973 (7) | 150 |
Hydrogen-bond geometry (Å, °)
| H⋯ | ||||
|---|---|---|---|---|
| N1—H1⋯O6 | 0.86 | 2.12 | 2.980 (6) | 173 |
| N1—H1⋯O5 | 0.86 | 2.46 | 3.029 (6) | 124 |
| N3—H3⋯O1 | 0.86 | 2.13 | 2.915 (7) | 151 |
| N3—H3⋯O2 | 0.86 | 2.64 | 3.143 (6) | 119 |
| N6—H6⋯O1 | 0.86 | 2.13 | 2.912 (6) | 150 |
| N8—H8⋯O4i | 0.86 | 2.33 | 3.073 (7) | 145 |
| O1 | 0.85 | 2.12 | 2.852 (6) | 144 |
| O1 | 0.85 | 2.04 | 2.888 (7) | 178 |
| O2 | 0.85 | 2.22 | 3.021 (7) | 157 |
| O2 | 0.85 | 2.21 | 2.973 (7) | 150 |
Symmetry codes: (i) ; (ii) .