| Literature DB >> 22090888 |
Abstract
The asymmetric unit of the title compound, {[Co(3)Yb(2)(C(5)H(2)N(2)O(4))(6)(H(2)O)(4)]·2H(2)O}(n), contains one Yb(III) ion, two Co(II) ions (one situated on an inversion centre), three imidazole-4,5-dicarboxyl-ate ligands, two coordinated water mol-ecules and one uncoordinated water mol-ecule. The Yb(III) ion is seven-coordinated, in a monocapped trigonal prismatic coordination geometry, by six O atoms from three imidazole-4,5-dicarboxyl-ate ligands and one water O atom. Both Co(II) ions are six-coordinated in a slightly distorted octa-hedral geometry. The Co(II) ion that is located on an inversion center is coordinated by two O atoms from two water mol-ecules, as well as two O atoms and two N atoms from two imidazole-4,5-dicarboxyl-ate ligands. The second Co(II) ion is bonded to four O atoms and two N atoms from four imidazole-4,5-dicarboxyl-ate ligands. These metal coordination units are connected by bridging imidazole-4,5-dicarboxyl-ate ligands, generating a three-dimensional network. The crystal structure is further stabilized by N-H⋯O, O-H⋯O and C-H⋯O hydrogen-bonding inter-actions involving the water mol-ecules and the imidazole-4,5-dicarboxyl-ate ligands.Entities:
Year: 2011 PMID: 22090888 PMCID: PMC3212186 DOI: 10.1107/S1600536811028285
Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN: 1600-5368
| [Co3Yb2(C5H2N2O4)6(H2O)4]·2H2O | |
| Triclinic, | |
| Hall symbol: -P 1 | Mo |
| Cell parameters from 3204 reflections | |
| θ = 2.5–28.0° | |
| µ = 5.81 mm−1 | |
| α = 95.546 (1)° | |
| β = 96.886 (1)° | Block, red |
| γ = 97.177 (1)° | 0.20 × 0.18 × 0.15 mm |
| Bruker APEXII area-detector diffractometer | 3640 independent reflections |
| Radiation source: fine-focus sealed tube | 3350 reflections with |
| graphite | |
| φ and ω scans | θmax = 25.2°, θmin = 2.3° |
| Absorption correction: multi-scan ( | |
| 5347 measured reflections |
| Refinement on | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| Hydrogen site location: inferred from neighbouring sites | |
| H atoms treated by a mixture of independent and constrained refinement | |
| 3640 reflections | (Δ/σ)max = 0.001 |
| 376 parameters | Δρmax = 0.78 e Å−3 |
| 12 restraints | Δρmin = −0.78 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 |
| Yb1 | 0.29829 (3) | 0.41070 (2) | 0.243626 (10) | 0.01363 (7) | |
| Co1 | 0.5000 | 0.0000 | 0.5000 | 0.01581 (18) | |
| Co2 | 0.61668 (8) | 0.93516 (6) | 0.07597 (3) | 0.01372 (13) | |
| C1 | 0.4567 (6) | 0.1646 (5) | 0.3642 (2) | 0.0139 (9) | |
| C2 | 0.5695 (6) | 0.2898 (5) | 0.4232 (2) | 0.0144 (9) | |
| C3 | 0.7118 (6) | 0.3644 (5) | 0.5375 (2) | 0.0200 (9) | |
| H3 | 0.7531 | 0.3657 | 0.5890 | 0.024* | |
| C4 | 0.6687 (6) | 0.4428 (5) | 0.4231 (2) | 0.0149 (9) | |
| C5 | 0.7011 (6) | 0.5510 (5) | 0.3626 (2) | 0.0183 (9) | |
| C6 | 0.3753 (6) | 0.2247 (5) | 0.0775 (2) | 0.0147 (9) | |
| C7 | 0.2950 (6) | 0.3342 (5) | 0.0250 (2) | 0.0131 (8) | |
| C8 | 0.1892 (6) | 0.3962 (5) | −0.0851 (2) | 0.0210 (10) | |
| H8 | 0.1429 | 0.3890 | −0.1365 | 0.025* | |
| C9 | 0.2778 (6) | 0.4982 (5) | 0.0341 (2) | 0.0142 (9) | |
| C10 | 0.3400 (6) | 0.6297 (5) | 0.0970 (2) | 0.0147 (9) | |
| C11 | 0.8955 (6) | 1.2012 (5) | 0.1572 (2) | 0.0155 (9) | |
| C12 | 0.8402 (6) | 1.1020 (5) | 0.2173 (2) | 0.0139 (8) | |
| C13 | 0.6907 (6) | 0.8844 (5) | 0.2507 (2) | 0.0222 (10) | |
| H13 | 0.6135 | 0.7851 | 0.2494 | 0.027* | |
| C14 | 0.8922 (6) | 1.1069 (5) | 0.2941 (2) | 0.0132 (8) | |
| C15 | 1.0131 (6) | 1.2253 (5) | 0.3539 (2) | 0.0153 (9) | |
| O1 | 0.4104 (4) | 0.0283 (3) | 0.38480 (16) | 0.0192 (6) | |
| O2 | 0.4150 (4) | 0.1990 (3) | 0.29715 (16) | 0.0213 (7) | |
| O3 | 0.8522 (4) | 0.6467 (4) | 0.37243 (18) | 0.0270 (7) | |
| O4 | 0.5683 (5) | 0.5394 (4) | 0.30733 (18) | 0.0297 (8) | |
| O5 | 0.4029 (5) | 0.2590 (3) | 0.14763 (16) | 0.0240 (7) | |
| O6 | 0.4133 (4) | 0.0941 (3) | 0.04421 (15) | 0.0155 (6) | |
| O7 | 0.3723 (4) | 0.5930 (3) | 0.16348 (16) | 0.0205 (7) | |
| O8 | 0.3603 (4) | 0.7716 (3) | 0.07878 (15) | 0.0185 (6) | |
| O9 | 0.8149 (4) | 1.1523 (3) | 0.09059 (15) | 0.0190 (6) | |
| O10 | 1.0184 (4) | 1.3279 (3) | 0.17219 (16) | 0.0235 (7) | |
| O11 | 1.1107 (4) | 1.3474 (3) | 0.33394 (16) | 0.0205 (7) | |
| O12 | 1.0107 (4) | 1.2009 (3) | 0.42250 (16) | 0.0203 (7) | |
| N1 | 0.5995 (5) | 0.2438 (4) | 0.49534 (19) | 0.0155 (7) | |
| N2 | 0.7592 (5) | 0.4862 (4) | 0.4960 (2) | 0.0175 (8) | |
| N3 | 0.2427 (5) | 0.2739 (4) | −0.05004 (19) | 0.0180 (8) | |
| N4 | 0.2106 (5) | 0.5326 (4) | −0.0366 (2) | 0.0184 (8) | |
| N5 | 0.7125 (5) | 0.9638 (4) | 0.19128 (19) | 0.0168 (8) | |
| N6 | 0.7947 (5) | 0.9664 (4) | 0.3127 (2) | 0.0195 (8) | |
| H1 | 0.824 (6) | 0.579 (3) | 0.515 (2) | 0.029* | |
| H2 | 0.190 (7) | 0.628 (3) | −0.047 (3) | 0.029* | |
| H4 | 0.801 (7) | 0.937 (5) | 0.3580 (15) | 0.029* | |
| O1W | 0.7736 (4) | −0.0471 (4) | 0.47573 (18) | 0.0246 (7) | |
| H1W | 0.830 (6) | −0.099 (5) | 0.506 (2) | 0.037* | |
| H2W | 0.842 (6) | 0.037 (3) | 0.475 (3) | 0.037* | |
| O2W | 0.1488 (5) | 0.6362 (4) | 0.2758 (2) | 0.0290 (8) | |
| H3W | 0.055 (5) | 0.640 (5) | 0.297 (3) | 0.044* | |
| H4W | 0.181 (7) | 0.728 (3) | 0.266 (3) | 0.044* | |
| O3W | 0.1955 (5) | 0.9104 (4) | 0.2090 (2) | 0.0338 (8) | |
| H5W | 0.250 (7) | 0.888 (6) | 0.1694 (19) | 0.051* | |
| H6W | 0.281 (6) | 0.978 (6) | 0.240 (2) | 0.051* |
| Yb1 | 0.01749 (11) | 0.01215 (10) | 0.00990 (10) | −0.00135 (7) | −0.00088 (7) | 0.00222 (7) |
| Co1 | 0.0187 (4) | 0.0159 (4) | 0.0130 (4) | 0.0003 (3) | 0.0010 (3) | 0.0064 (3) |
| Co2 | 0.0201 (3) | 0.0096 (3) | 0.0100 (3) | 0.0011 (2) | −0.0023 (2) | 0.0004 (2) |
| C1 | 0.013 (2) | 0.015 (2) | 0.014 (2) | 0.0057 (17) | 0.0015 (17) | −0.0011 (17) |
| C2 | 0.017 (2) | 0.014 (2) | 0.012 (2) | 0.0024 (17) | 0.0014 (17) | 0.0046 (17) |
| C3 | 0.027 (3) | 0.020 (2) | 0.012 (2) | 0.0045 (19) | −0.0026 (18) | 0.0021 (18) |
| C4 | 0.012 (2) | 0.017 (2) | 0.016 (2) | 0.0047 (17) | 0.0015 (17) | 0.0040 (17) |
| C5 | 0.023 (2) | 0.013 (2) | 0.019 (2) | 0.0018 (18) | −0.0009 (19) | 0.0052 (18) |
| C6 | 0.014 (2) | 0.017 (2) | 0.013 (2) | 0.0027 (17) | 0.0016 (17) | 0.0026 (17) |
| C7 | 0.015 (2) | 0.013 (2) | 0.010 (2) | 0.0000 (17) | 0.0013 (16) | −0.0002 (16) |
| C8 | 0.029 (3) | 0.023 (2) | 0.011 (2) | 0.007 (2) | −0.0036 (18) | 0.0017 (18) |
| C9 | 0.018 (2) | 0.015 (2) | 0.009 (2) | 0.0014 (17) | −0.0010 (17) | 0.0022 (16) |
| C10 | 0.014 (2) | 0.019 (2) | 0.013 (2) | 0.0029 (17) | 0.0020 (16) | 0.0061 (17) |
| C11 | 0.017 (2) | 0.016 (2) | 0.014 (2) | 0.0041 (18) | −0.0013 (17) | 0.0034 (17) |
| C12 | 0.014 (2) | 0.011 (2) | 0.016 (2) | 0.0025 (16) | −0.0012 (17) | 0.0008 (17) |
| C13 | 0.025 (3) | 0.019 (2) | 0.019 (2) | −0.0059 (19) | −0.0009 (19) | 0.0025 (19) |
| C14 | 0.014 (2) | 0.014 (2) | 0.012 (2) | 0.0029 (17) | −0.0001 (16) | 0.0033 (17) |
| C15 | 0.015 (2) | 0.017 (2) | 0.015 (2) | 0.0079 (18) | 0.0012 (17) | 0.0022 (18) |
| O1 | 0.0273 (17) | 0.0132 (15) | 0.0150 (16) | −0.0028 (13) | −0.0022 (13) | 0.0040 (12) |
| O2 | 0.0328 (18) | 0.0164 (15) | 0.0131 (16) | 0.0015 (13) | −0.0028 (13) | 0.0036 (12) |
| O3 | 0.0205 (17) | 0.0268 (17) | 0.0309 (19) | −0.0070 (14) | −0.0046 (14) | 0.0122 (15) |
| O4 | 0.0334 (19) | 0.0232 (17) | 0.0273 (18) | −0.0096 (15) | −0.0108 (15) | 0.0125 (15) |
| O5 | 0.042 (2) | 0.0211 (16) | 0.0106 (16) | 0.0132 (15) | 0.0020 (14) | 0.0009 (13) |
| O6 | 0.0248 (16) | 0.0087 (14) | 0.0128 (15) | 0.0046 (12) | 0.0008 (12) | −0.0012 (12) |
| O7 | 0.0355 (19) | 0.0133 (14) | 0.0113 (15) | −0.0018 (13) | 0.0013 (13) | 0.0026 (12) |
| O8 | 0.0272 (17) | 0.0119 (14) | 0.0156 (15) | −0.0011 (13) | 0.0001 (13) | 0.0059 (12) |
| O9 | 0.0251 (17) | 0.0167 (15) | 0.0115 (15) | −0.0068 (13) | −0.0031 (13) | 0.0029 (12) |
| O10 | 0.0255 (17) | 0.0207 (16) | 0.0194 (17) | −0.0112 (14) | −0.0052 (13) | 0.0063 (13) |
| O11 | 0.0247 (17) | 0.0195 (16) | 0.0146 (16) | −0.0056 (13) | 0.0011 (13) | 0.0006 (13) |
| O12 | 0.0239 (17) | 0.0230 (16) | 0.0138 (16) | 0.0018 (13) | 0.0027 (13) | 0.0028 (13) |
| N1 | 0.0207 (19) | 0.0152 (18) | 0.0110 (18) | 0.0034 (15) | 0.0008 (14) | 0.0039 (14) |
| N2 | 0.021 (2) | 0.0134 (18) | 0.0153 (19) | −0.0031 (15) | −0.0032 (15) | 0.0006 (15) |
| N3 | 0.023 (2) | 0.0166 (18) | 0.0128 (18) | 0.0017 (15) | −0.0025 (15) | −0.0007 (15) |
| N4 | 0.027 (2) | 0.0142 (18) | 0.0155 (19) | 0.0071 (16) | 0.0000 (16) | 0.0045 (15) |
| N5 | 0.023 (2) | 0.0114 (17) | 0.0144 (18) | −0.0020 (15) | −0.0007 (15) | 0.0023 (14) |
| N6 | 0.028 (2) | 0.0189 (19) | 0.0108 (19) | −0.0012 (16) | −0.0019 (16) | 0.0080 (16) |
| O1W | 0.0204 (18) | 0.0289 (18) | 0.0264 (18) | 0.0038 (14) | 0.0031 (14) | 0.0127 (15) |
| O2W | 0.036 (2) | 0.0202 (17) | 0.035 (2) | 0.0044 (16) | 0.0169 (16) | 0.0079 (15) |
| O3W | 0.041 (2) | 0.0250 (19) | 0.035 (2) | 0.0032 (16) | 0.0108 (17) | −0.0038 (16) |
| Yb1—O4 | 2.191 (3) | C7—C9 | 1.386 (5) |
| Yb1—O10i | 2.209 (3) | C8—N3 | 1.320 (5) |
| Yb1—O7 | 2.246 (3) | C8—N4 | 1.344 (5) |
| Yb1—O11i | 2.266 (3) | C8—H8 | 0.9300 |
| Yb1—O5 | 2.282 (3) | C9—N4 | 1.366 (5) |
| Yb1—O2 | 2.285 (3) | C9—C10 | 1.479 (6) |
| Yb1—O2W | 2.328 (3) | C10—O8 | 1.254 (5) |
| Co1—N1ii | 2.082 (3) | C10—O7 | 1.257 (5) |
| Co1—N1 | 2.082 (3) | C11—O9 | 1.262 (5) |
| Co1—O1W | 2.100 (3) | C11—O10 | 1.265 (5) |
| Co1—O1Wii | 2.100 (3) | C11—C12 | 1.478 (5) |
| Co1—O1ii | 2.125 (3) | C12—C14 | 1.374 (5) |
| Co1—O1 | 2.125 (3) | C12—N5 | 1.376 (5) |
| Co2—N5 | 2.072 (3) | C13—N5 | 1.320 (5) |
| Co2—O9 | 2.120 (3) | C13—N6 | 1.330 (6) |
| Co2—O6iii | 2.120 (3) | C13—H13 | 0.9300 |
| Co2—O8 | 2.132 (3) | C14—N6 | 1.374 (5) |
| Co2—O6iv | 2.136 (3) | C14—C15 | 1.487 (6) |
| Co2—N3iii | 2.152 (3) | C15—O11 | 1.262 (5) |
| C1—O1 | 1.247 (5) | C15—O12 | 1.264 (5) |
| C1—O2 | 1.268 (5) | O6—Co2iii | 2.120 (3) |
| C1—C2 | 1.489 (5) | O6—Co2v | 2.136 (3) |
| C2—C4 | 1.378 (6) | O10—Yb1vi | 2.209 (3) |
| C2—N1 | 1.380 (5) | O11—Yb1vi | 2.266 (3) |
| C3—N1 | 1.312 (5) | N2—H1 | 0.867 (19) |
| C3—N2 | 1.347 (5) | N3—Co2iii | 2.152 (3) |
| C3—H3 | 0.9300 | N4—H2 | 0.863 (19) |
| C4—N2 | 1.374 (5) | N6—H4 | 0.865 (19) |
| C4—C5 | 1.496 (5) | O1W—H1W | 0.82 (4) |
| C5—O3 | 1.232 (5) | O1W—H2W | 0.804 (19) |
| C5—O4 | 1.264 (5) | O2W—H3W | 0.80 (4) |
| C6—O5 | 1.245 (5) | O2W—H4W | 0.811 (19) |
| C6—O6 | 1.265 (5) | O3W—H5W | 0.86 (4) |
| C6—C7 | 1.484 (5) | O3W—H6W | 0.87 (4) |
| C7—N3 | 1.376 (5) | ||
| O4—Yb1—O10i | 168.77 (11) | O5—C6—C7 | 122.9 (4) |
| O4—Yb1—O7 | 80.61 (11) | O6—C6—C7 | 113.7 (3) |
| O10i—Yb1—O7 | 89.98 (10) | N3—C7—C9 | 109.4 (3) |
| O4—Yb1—O11i | 104.42 (11) | N3—C7—C6 | 117.8 (3) |
| O10i—Yb1—O11i | 79.80 (11) | C9—C7—C6 | 132.4 (4) |
| O7—Yb1—O11i | 144.82 (11) | N3—C8—N4 | 110.9 (4) |
| O4—Yb1—O5 | 102.77 (12) | N3—C8—H8 | 124.6 |
| O10i—Yb1—O5 | 80.83 (11) | N4—C8—H8 | 124.6 |
| O7—Yb1—O5 | 76.85 (10) | N4—C9—C7 | 104.8 (3) |
| O11i—Yb1—O5 | 133.18 (10) | N4—C9—C10 | 120.7 (3) |
| O4—Yb1—O2 | 80.51 (11) | C7—C9—C10 | 133.8 (4) |
| O10i—Yb1—O2 | 110.72 (10) | O8—C10—O7 | 124.9 (4) |
| O7—Yb1—O2 | 140.86 (11) | O8—C10—C9 | 116.2 (3) |
| O11i—Yb1—O2 | 73.46 (11) | O7—C10—C9 | 118.9 (3) |
| O5—Yb1—O2 | 74.36 (10) | O9—C11—O10 | 122.2 (4) |
| O4—Yb1—O2W | 88.67 (13) | O9—C11—C12 | 116.5 (4) |
| O10i—Yb1—O2W | 82.67 (12) | O10—C11—C12 | 121.3 (4) |
| O7—Yb1—O2W | 72.93 (11) | C14—C12—N5 | 109.5 (3) |
| O11i—Yb1—O2W | 72.42 (11) | C14—C12—C11 | 136.1 (4) |
| O5—Yb1—O2W | 145.39 (11) | N5—C12—C11 | 114.2 (3) |
| O2—Yb1—O2W | 140.19 (11) | N5—C13—N6 | 110.4 (4) |
| N1ii—Co1—N1 | 180.000 (1) | N5—C13—H13 | 124.8 |
| N1ii—Co1—O1W | 93.48 (13) | N6—C13—H13 | 124.8 |
| N1—Co1—O1W | 86.52 (13) | N6—C14—C12 | 104.4 (3) |
| N1ii—Co1—O1Wii | 86.52 (13) | N6—C14—C15 | 120.5 (3) |
| N1—Co1—O1Wii | 93.48 (13) | C12—C14—C15 | 135.1 (4) |
| O1W—Co1—O1Wii | 180.000 (1) | O11—C15—O12 | 122.9 (4) |
| N1ii—Co1—O1ii | 77.93 (12) | O11—C15—C14 | 118.5 (4) |
| N1—Co1—O1ii | 102.07 (12) | O12—C15—C14 | 118.6 (4) |
| O1W—Co1—O1ii | 88.35 (12) | C1—O1—Co1 | 116.7 (3) |
| O1Wii—Co1—O1ii | 91.65 (12) | C1—O2—Yb1 | 135.6 (3) |
| N1ii—Co1—O1 | 102.07 (12) | C5—O4—Yb1 | 149.7 (3) |
| N1—Co1—O1 | 77.93 (12) | C6—O5—Yb1 | 141.9 (3) |
| O1W—Co1—O1 | 91.65 (12) | C6—O6—Co2iii | 118.5 (2) |
| O1Wii—Co1—O1 | 88.35 (12) | C6—O6—Co2v | 131.8 (3) |
| O1ii—Co1—O1 | 180.0 | Co2iii—O6—Co2v | 103.63 (11) |
| N5—Co2—O9 | 77.03 (12) | C10—O7—Yb1 | 145.5 (3) |
| N5—Co2—O6iii | 166.83 (12) | C10—O8—Co2 | 130.1 (3) |
| O9—Co2—O6iii | 95.87 (10) | C11—O9—Co2 | 116.9 (3) |
| N5—Co2—O8 | 97.27 (12) | C11—O10—Yb1vi | 138.7 (3) |
| O9—Co2—O8 | 160.59 (11) | C15—O11—Yb1vi | 139.5 (3) |
| O6iii—Co2—O8 | 92.93 (11) | C3—N1—C2 | 106.8 (3) |
| N5—Co2—O6iv | 113.16 (12) | C3—N1—Co1 | 138.9 (3) |
| O9—Co2—O6iv | 82.90 (11) | C2—N1—Co1 | 113.1 (3) |
| O6iii—Co2—O6iv | 76.37 (11) | C3—N2—C4 | 108.2 (3) |
| O8—Co2—O6iv | 82.41 (11) | C3—N2—H1 | 124 (3) |
| N5—Co2—N3iii | 95.60 (13) | C4—N2—H1 | 127 (3) |
| O9—Co2—N3iii | 111.27 (12) | C8—N3—C7 | 106.1 (3) |
| O6iii—Co2—N3iii | 76.47 (11) | C8—N3—Co2iii | 137.1 (3) |
| O8—Co2—N3iii | 87.60 (12) | C7—N3—Co2iii | 109.9 (3) |
| O6iv—Co2—N3iii | 150.46 (12) | C8—N4—C9 | 108.7 (3) |
| O1—C1—O2 | 123.8 (4) | C8—N4—H2 | 127 (3) |
| O1—C1—C2 | 116.2 (3) | C9—N4—H2 | 124 (3) |
| O2—C1—C2 | 120.0 (3) | C13—N5—C12 | 106.3 (3) |
| C4—C2—N1 | 108.8 (4) | C13—N5—Co2 | 138.5 (3) |
| C4—C2—C1 | 135.1 (4) | C12—N5—Co2 | 115.2 (3) |
| N1—C2—C1 | 115.9 (3) | C13—N6—C14 | 109.4 (4) |
| N1—C3—N2 | 110.7 (4) | C13—N6—H4 | 126 (3) |
| N1—C3—H3 | 124.6 | C14—N6—H4 | 125 (3) |
| N2—C3—H3 | 124.6 | Co1—O1W—H1W | 115 (4) |
| N2—C4—C2 | 105.4 (4) | Co1—O1W—H2W | 110 (4) |
| N2—C4—C5 | 120.7 (4) | H1W—O1W—H2W | 107 (3) |
| C2—C4—C5 | 133.8 (4) | Yb1—O2W—H3W | 128 (3) |
| O3—C5—O4 | 126.0 (4) | Yb1—O2W—H4W | 126 (3) |
| O3—C5—C4 | 116.9 (4) | H3W—O2W—H4W | 106 (3) |
| O4—C5—C4 | 117.0 (4) | H5W—O3W—H6W | 106 (3) |
| O5—C6—O6 | 123.4 (4) |
| H··· | ||||
| N2—H1···O12vii | 0.87 (3) | 2.18 (3) | 3.036 (4) | 172 (3) |
| O1W—H1W···O12viii | 0.82 (4) | 1.93 (4) | 2.747 (4) | 173 (4) |
| N4—H2···O9ix | 0.86 (3) | 2.07 (3) | 2.909 (4) | 166 (5) |
| O1W—H2W···O12v | 0.80 (3) | 2.07 (4) | 2.808 (4) | 153 (5) |
| O2W—H3W···O3x | 0.80 (4) | 2.08 (4) | 2.870 (5) | 168 (5) |
| N6—H4···O1Wiv | 0.87 (3) | 2.13 (3) | 2.948 (5) | 157 (4) |
| N6—H4···O3 | 0.87 (3) | 2.53 (4) | 3.026 (5) | 117 (3) |
| O2W—H4W···O3W | 0.81 (3) | 1.91 (4) | 2.686 (5) | 159 (5) |
| O3W—H5W···O8 | 0.86 (4) | 2.09 (4) | 2.928 (4) | 165 (5) |
| O3W—H6W···O2iv | 0.87 (4) | 2.08 (5) | 2.904 (4) | 158 (4) |
| C3—H3···O2Wxi | 0.93 | 2.43 | 3.365 (5) | 178 |
| C13—H13···O4 | 0.93 | 2.39 | 3.198 (5) | 145 |
| C13—H13···O7 | 0.93 | 2.46 | 3.232 (5) | 141 |
Hydrogen-bond geometry (Å, °)
| H⋯ | ||||
|---|---|---|---|---|
| N2—H1⋯O12i | 0.87 (3) | 2.18 (3) | 3.036 (4) | 172 (3) |
| O1 | 0.82 (4) | 1.93 (4) | 2.747 (4) | 173 (4) |
| N4—H2⋯O9iii | 0.86 (3) | 2.07 (3) | 2.909 (4) | 166 (5) |
| O1 | 0.80 (3) | 2.07 (4) | 2.808 (4) | 153 (5) |
| O2 | 0.80 (4) | 2.08 (4) | 2.870 (5) | 168 (5) |
| N6—H4⋯O1 | 0.87 (3) | 2.13 (3) | 2.948 (5) | 157 (4) |
| N6—H4⋯O3 | 0.87 (3) | 2.53 (4) | 3.026 (5) | 117 (3) |
| O2 | 0.81 (3) | 1.91 (4) | 2.686 (5) | 159 (5) |
| O3 | 0.86 (4) | 2.09 (4) | 2.928 (4) | 165 (5) |
| O3 | 0.87 (4) | 2.08 (5) | 2.904 (4) | 158 (4) |
| C3—H3⋯O2 | 0.93 | 2.43 | 3.365 (5) | 178 |
| C13—H13⋯O4 | 0.93 | 2.39 | 3.198 (5) | 145 |
| C13—H13⋯O7 | 0.93 | 2.46 | 3.232 (5) | 141 |
Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .