| Literature DB >> 21580551 |
Janet Soleimannejad, Jafar Attar Gharamaleki, Hossein Aghabozorg, Yaghoub Mohammadzadeh Azar Golenji.
Abstract
The title compound, (C(10)H(10)N(2))[Sb(2)(C(7)H(2)NO(5))(2)(OH)(2)(H(2)O)(2)]·2H(2)O, consists of a binuclear anion, a diprotonated 4,4'-bipyridinium cation and two uncoordinated water mol-ecules. Each Sb(III) atom is six-coordinated by one chelating 4-oxidopyridine-2,6-dicarboxyl-ate ligand, one water mol-ecule, one OH group and one bridging O atom from a neighboring carboxyl-ate group in a distorted penta-gonal-pyramidal geometry, with the OH group at the apical position. The two pyridine rings in the bipyridinium cation are twisted with respect to each other, making a dihedral angle of 22.7 (1)°. The cations are connected to the anions by N-H⋯O hydrogen bonds, forming a chain. The coordinated water mol-ecules form hydrogen bonds with the oxido O atoms of the anion, building a two-dimensional sheet, which is further connected into a three-dimensional structure by O-H⋯O and C-H⋯O hydrogen bonds and C=O⋯π inter-actions [O⋯centroid distances = 3.1785 (17), 3.4737 (19) and 3.5685 (19) Å].Entities:
Year: 2010 PMID: 21580551 PMCID: PMC2983914 DOI: 10.1107/S1600536810010743
Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN: 1600-5368
| (C10H10N2)[Sb2(C7H2NO5)2(OH)2(H2O)2]·2H2O | |
| Triclinic, | |
| Hall symbol: -P 1 | Mo |
| Cell parameters from 16661 reflections | |
| θ = 2.5–27.5° | |
| µ = 2.06 mm−1 | |
| α = 80.255 (5)° | |
| β = 81.760 (5)° | Block, colourless |
| γ = 82.547 (5)° | 0.32 × 0.32 × 0.13 mm |
| Bruker SMART 1000 CCD diffractometer | 6323 independent reflections |
| Radiation source: fine-focus sealed tube | 5762 reflections with |
| graphite | |
| φ and ω scans | θmax = 27.6°, θmin = 1.2° |
| Absorption correction: multi-scan ( | |
| 29846 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-atom parameters constrained | |
| 6323 reflections | (Δ/σ)max = 0.002 |
| 415 parameters | Δρmax = 1.02 e Å−3 |
| 0 restraints | Δρmin = −0.61 e Å−3 |
| Sb1 | 0.580591 (16) | 0.703688 (13) | 0.358013 (7) | 0.01090 (4) | |
| Sb2 | 0.438680 (16) | 0.752017 (12) | 0.129483 (7) | 0.01011 (4) | |
| O1W | 0.11728 (19) | 0.69329 (15) | 0.33900 (9) | 0.0163 (3) | |
| H1A | 0.1420 | 0.6243 | 0.3712 | 0.020* | |
| H1B | 0.0115 | 0.6949 | 0.3314 | 0.020* | |
| O1 | 0.72456 (19) | 0.67130 (15) | 0.45745 (8) | 0.0150 (3) | |
| O2W | 0.9042 (2) | 0.8814 (2) | 0.17638 (12) | 0.0439 (6) | |
| H2A | 0.8878 | 0.9460 | 0.1396 | 0.053* | |
| H2B | 1.0123 | 0.8520 | 0.1710 | 0.053* | |
| O2 | 0.8151 (2) | 0.52864 (15) | 0.55669 (9) | 0.0170 (3) | |
| O3 | 0.7165 (2) | 0.08698 (15) | 0.46954 (9) | 0.0189 (3) | |
| O4 | 0.4341 (2) | 0.39130 (15) | 0.24797 (9) | 0.0172 (3) | |
| O5 | 0.49471 (19) | 0.58946 (14) | 0.26877 (8) | 0.0141 (3) | |
| O6 | 0.30385 (19) | 0.77857 (14) | 0.02920 (8) | 0.0145 (3) | |
| O7 | 0.1851 (2) | 0.91893 (15) | −0.06395 (9) | 0.0186 (3) | |
| O8 | 0.23816 (19) | 1.36547 (14) | 0.03077 (8) | 0.0144 (3) | |
| O9 | 0.5309 (2) | 1.06860 (15) | 0.25055 (9) | 0.0221 (4) | |
| O10 | 0.49467 (19) | 0.86694 (14) | 0.22539 (8) | 0.0137 (3) | |
| O11 | 0.80104 (18) | 0.69280 (15) | 0.29264 (8) | 0.0155 (3) | |
| H11A | 0.7985 | 0.7579 | 0.2560 | 0.019* | |
| O13 | 0.6824 (3) | 0.92019 (17) | 0.36682 (10) | 0.0296 (4) | |
| H13B | 0.6856 | 0.9689 | 0.4007 | 0.035* | |
| H13A | 0.6356 | 0.9734 | 0.3315 | 0.035* | |
| O15 | 0.4245 (2) | 0.51911 (15) | 0.10194 (9) | 0.0172 (3) | |
| H15B | 0.3615 | 0.4804 | 0.0792 | 0.021* | |
| H15A | 0.4127 | 0.4729 | 0.1465 | 0.021* | |
| O16 | 0.21023 (18) | 0.73191 (15) | 0.18620 (8) | 0.0146 (3) | |
| H16A | 0.2120 | 0.7088 | 0.2346 | 0.018* | |
| N1 | 0.6307 (2) | 0.48763 (17) | 0.39380 (10) | 0.0111 (3) | |
| N2 | 0.3608 (2) | 0.96575 (17) | 0.09960 (9) | 0.0109 (3) | |
| N3 | −0.1645 (2) | 0.95121 (18) | −0.40617 (10) | 0.0148 (4) | |
| H3A | −0.2043 | 1.0024 | −0.4440 | 0.018* | |
| N4 | 0.1423 (2) | 0.50965 (18) | −0.09767 (10) | 0.0141 (3) | |
| H4A | 0.1802 | 0.4608 | −0.0586 | 0.017* | |
| C1 | 0.7559 (3) | 0.5527 (2) | 0.49466 (12) | 0.0128 (4) | |
| C2 | 0.7105 (3) | 0.4426 (2) | 0.45717 (11) | 0.0111 (4) | |
| C3 | 0.7429 (3) | 0.3094 (2) | 0.48443 (12) | 0.0128 (4) | |
| H3 | 0.7997 | 0.2821 | 0.5279 | 0.015* | |
| C4 | 0.6890 (3) | 0.2126 (2) | 0.44593 (11) | 0.0131 (4) | |
| C5 | 0.6039 (3) | 0.2645 (2) | 0.37913 (12) | 0.0132 (4) | |
| H5 | 0.5654 | 0.2068 | 0.3516 | 0.016* | |
| C6 | 0.5793 (3) | 0.3989 (2) | 0.35577 (11) | 0.0113 (4) | |
| C7 | 0.4945 (3) | 0.4624 (2) | 0.28500 (11) | 0.0117 (4) | |
| C8 | 0.2517 (3) | 0.8969 (2) | −0.00416 (12) | 0.0128 (4) | |
| C9 | 0.2806 (3) | 1.0087 (2) | 0.03616 (11) | 0.0116 (4) | |
| C10 | 0.2339 (3) | 1.1418 (2) | 0.01168 (11) | 0.0117 (4) | |
| H10 | 0.1768 | 1.1676 | −0.0319 | 0.014* | |
| C11 | 0.2727 (3) | 1.2403 (2) | 0.05286 (11) | 0.0114 (4) | |
| C12 | 0.3553 (3) | 1.1902 (2) | 0.12072 (12) | 0.0129 (4) | |
| H12 | 0.3818 | 1.2491 | 0.1508 | 0.016* | |
| C13 | 0.3953 (3) | 1.0562 (2) | 0.14123 (11) | 0.0117 (4) | |
| C14 | 0.4814 (3) | 0.9955 (2) | 0.21167 (12) | 0.0133 (4) | |
| C15 | 0.1954 (3) | 0.6317 (2) | −0.11368 (12) | 0.0146 (4) | |
| H15 | 0.2685 | 0.6569 | −0.0829 | 0.017* | |
| C16 | 0.1420 (3) | 0.7203 (2) | −0.17571 (12) | 0.0142 (4) | |
| H16 | 0.1806 | 0.8044 | −0.1873 | 0.017* | |
| C17 | 0.0292 (3) | 0.6824 (2) | −0.22106 (11) | 0.0118 (4) | |
| C18 | −0.0372 (3) | 0.7772 (2) | −0.28624 (11) | 0.0118 (4) | |
| C19 | −0.0412 (3) | 0.9149 (2) | −0.28961 (12) | 0.0155 (4) | |
| H19 | −0.0004 | 0.9490 | −0.2510 | 0.019* | |
| C20 | −0.1056 (3) | 1.0000 (2) | −0.35033 (12) | 0.0170 (4) | |
| H20 | −0.1082 | 1.0916 | −0.3526 | 0.020* | |
| C21 | −0.1612 (3) | 0.8204 (2) | −0.40566 (12) | 0.0153 (4) | |
| H21 | −0.2014 | 0.7896 | −0.4455 | 0.018* | |
| C22 | −0.0982 (3) | 0.7308 (2) | −0.34594 (12) | 0.0139 (4) | |
| H22 | −0.0964 | 0.6397 | −0.3455 | 0.017* | |
| C23 | −0.0233 (3) | 0.5547 (2) | −0.20217 (12) | 0.0148 (4) | |
| H23 | −0.0977 | 0.5270 | −0.2314 | 0.018* | |
| C24 | 0.0355 (3) | 0.4695 (2) | −0.14003 (12) | 0.0154 (4) | |
| H24 | 0.0010 | 0.3841 | −0.1275 | 0.019* |
| Sb1 | 0.01408 (7) | 0.00955 (7) | 0.00914 (7) | −0.00086 (5) | −0.00371 (5) | −0.00003 (5) |
| Sb2 | 0.01203 (7) | 0.00898 (7) | 0.00915 (7) | −0.00093 (5) | −0.00270 (5) | 0.00010 (5) |
| O1W | 0.0153 (7) | 0.0179 (8) | 0.0148 (7) | −0.0018 (6) | −0.0057 (6) | 0.0032 (6) |
| O1 | 0.0225 (8) | 0.0107 (7) | 0.0125 (7) | −0.0030 (6) | −0.0072 (6) | 0.0011 (6) |
| O2W | 0.0242 (9) | 0.0498 (13) | 0.0392 (12) | 0.0090 (9) | 0.0027 (8) | 0.0303 (10) |
| O2 | 0.0273 (8) | 0.0135 (7) | 0.0117 (7) | −0.0020 (6) | −0.0095 (6) | −0.0005 (6) |
| O3 | 0.0331 (9) | 0.0092 (7) | 0.0156 (7) | −0.0017 (6) | −0.0117 (6) | 0.0016 (6) |
| O4 | 0.0273 (8) | 0.0122 (7) | 0.0145 (7) | −0.0043 (6) | −0.0110 (6) | 0.0000 (6) |
| O5 | 0.0191 (7) | 0.0102 (7) | 0.0139 (7) | −0.0020 (6) | −0.0069 (6) | 0.0003 (6) |
| O6 | 0.0214 (7) | 0.0097 (7) | 0.0134 (7) | −0.0017 (6) | −0.0070 (6) | −0.0001 (6) |
| O7 | 0.0302 (8) | 0.0138 (7) | 0.0139 (7) | −0.0005 (6) | −0.0122 (6) | −0.0013 (6) |
| O8 | 0.0220 (7) | 0.0084 (7) | 0.0128 (7) | −0.0002 (6) | −0.0066 (6) | 0.0011 (5) |
| O9 | 0.0396 (10) | 0.0115 (7) | 0.0190 (8) | −0.0024 (7) | −0.0175 (7) | −0.0012 (6) |
| O10 | 0.0197 (7) | 0.0086 (7) | 0.0135 (7) | −0.0017 (6) | −0.0063 (6) | 0.0001 (6) |
| O11 | 0.0145 (7) | 0.0172 (8) | 0.0131 (7) | −0.0020 (6) | −0.0030 (6) | 0.0035 (6) |
| O13 | 0.0574 (12) | 0.0132 (8) | 0.0231 (9) | −0.0055 (8) | −0.0228 (8) | −0.0006 (7) |
| O15 | 0.0258 (8) | 0.0110 (7) | 0.0162 (7) | −0.0043 (6) | −0.0087 (6) | 0.0006 (6) |
| O16 | 0.0139 (7) | 0.0180 (8) | 0.0112 (7) | −0.0031 (6) | −0.0021 (5) | 0.0012 (6) |
| N1 | 0.0140 (8) | 0.0104 (8) | 0.0089 (8) | −0.0012 (6) | −0.0033 (6) | 0.0001 (6) |
| N2 | 0.0131 (8) | 0.0098 (8) | 0.0096 (8) | −0.0008 (6) | −0.0028 (6) | 0.0000 (6) |
| N3 | 0.0184 (8) | 0.0148 (9) | 0.0105 (8) | −0.0016 (7) | −0.0050 (7) | 0.0030 (7) |
| N4 | 0.0177 (8) | 0.0129 (8) | 0.0106 (8) | 0.0020 (7) | −0.0042 (7) | 0.0003 (7) |
| C1 | 0.0151 (9) | 0.0120 (9) | 0.0110 (9) | −0.0006 (7) | −0.0016 (7) | −0.0018 (8) |
| C2 | 0.0124 (9) | 0.0135 (10) | 0.0079 (9) | −0.0028 (7) | −0.0020 (7) | −0.0012 (7) |
| C3 | 0.0160 (9) | 0.0126 (10) | 0.0094 (9) | −0.0013 (7) | −0.0041 (7) | 0.0015 (7) |
| C4 | 0.0170 (9) | 0.0115 (9) | 0.0103 (9) | −0.0012 (8) | −0.0024 (7) | 0.0000 (7) |
| C5 | 0.0161 (9) | 0.0129 (10) | 0.0113 (9) | −0.0022 (7) | −0.0034 (7) | −0.0014 (8) |
| C6 | 0.0122 (9) | 0.0127 (9) | 0.0090 (9) | −0.0013 (7) | −0.0025 (7) | −0.0011 (7) |
| C7 | 0.0129 (9) | 0.0110 (9) | 0.0100 (9) | 0.0005 (7) | −0.0022 (7) | 0.0010 (7) |
| C8 | 0.0155 (9) | 0.0111 (9) | 0.0114 (9) | −0.0024 (7) | −0.0016 (7) | −0.0003 (8) |
| C9 | 0.0127 (9) | 0.0123 (10) | 0.0097 (9) | −0.0014 (7) | −0.0012 (7) | −0.0012 (7) |
| C10 | 0.0130 (9) | 0.0130 (10) | 0.0090 (9) | −0.0018 (7) | −0.0038 (7) | 0.0005 (7) |
| C11 | 0.0132 (9) | 0.0104 (9) | 0.0095 (9) | −0.0004 (7) | −0.0002 (7) | 0.0002 (7) |
| C12 | 0.0161 (9) | 0.0112 (10) | 0.0113 (9) | −0.0014 (7) | −0.0032 (7) | −0.0003 (8) |
| C13 | 0.0137 (9) | 0.0114 (9) | 0.0099 (9) | −0.0011 (7) | −0.0023 (7) | −0.0010 (7) |
| C14 | 0.0167 (9) | 0.0117 (10) | 0.0111 (9) | −0.0010 (7) | −0.0041 (7) | 0.0005 (8) |
| C15 | 0.0153 (9) | 0.0144 (10) | 0.0157 (10) | −0.0015 (8) | −0.0054 (8) | −0.0045 (8) |
| C16 | 0.0166 (9) | 0.0115 (10) | 0.0153 (10) | −0.0033 (8) | −0.0035 (8) | −0.0012 (8) |
| C17 | 0.0121 (9) | 0.0118 (9) | 0.0105 (9) | 0.0002 (7) | 0.0001 (7) | −0.0016 (8) |
| C18 | 0.0121 (9) | 0.0115 (9) | 0.0112 (9) | −0.0021 (7) | −0.0017 (7) | 0.0007 (8) |
| C19 | 0.0215 (10) | 0.0133 (10) | 0.0129 (10) | −0.0029 (8) | −0.0054 (8) | −0.0019 (8) |
| C20 | 0.0224 (10) | 0.0133 (10) | 0.0158 (10) | −0.0026 (8) | −0.0053 (8) | −0.0007 (8) |
| C21 | 0.0179 (10) | 0.0169 (10) | 0.0120 (10) | −0.0035 (8) | −0.0051 (8) | −0.0010 (8) |
| C22 | 0.0177 (10) | 0.0118 (10) | 0.0128 (10) | −0.0031 (8) | −0.0040 (8) | −0.0011 (8) |
| C23 | 0.0171 (10) | 0.0147 (10) | 0.0140 (10) | −0.0035 (8) | −0.0061 (8) | −0.0012 (8) |
| C24 | 0.0195 (10) | 0.0120 (10) | 0.0152 (10) | −0.0032 (8) | −0.0048 (8) | 0.0004 (8) |
| Sb1—O11 | 1.9300 (15) | N3—H3A | 0.8500 |
| Sb1—O1 | 2.1816 (14) | N4—C15 | 1.340 (3) |
| Sb1—N1 | 2.1972 (17) | N4—C24 | 1.341 (3) |
| Sb1—O5 | 2.3381 (15) | N4—H4A | 0.8500 |
| Sb1—O13 | 2.4861 (17) | C1—C2 | 1.505 (3) |
| Sb1—O10 | 2.7617 (14) | C2—C3 | 1.372 (3) |
| Sb2—O16 | 1.9304 (14) | C3—C4 | 1.431 (3) |
| Sb2—O6 | 2.1559 (14) | C3—H3 | 0.9300 |
| Sb2—N2 | 2.1908 (17) | C4—C5 | 1.432 (3) |
| Sb2—O10 | 2.3468 (15) | C5—C6 | 1.366 (3) |
| Sb2—O15 | 2.5350 (15) | C5—H5 | 0.9300 |
| Sb2—O5 | 2.7959 (14) | C6—C7 | 1.513 (3) |
| O1W—H1A | 0.8500 | C8—C9 | 1.506 (3) |
| O1W—H1B | 0.8500 | C9—C10 | 1.378 (3) |
| O1—C1 | 1.293 (2) | C10—C11 | 1.428 (3) |
| O2W—H2A | 0.8589 | C10—H10 | 0.9300 |
| O2W—H2B | 0.8529 | C11—C12 | 1.435 (3) |
| O2—C1 | 1.230 (2) | C12—C13 | 1.366 (3) |
| O3—C4 | 1.284 (3) | C12—H12 | 0.9300 |
| O4—C7 | 1.235 (3) | C13—C14 | 1.507 (3) |
| O5—C7 | 1.285 (3) | C15—C16 | 1.380 (3) |
| O6—C8 | 1.297 (2) | C15—H15 | 0.9300 |
| O7—C8 | 1.223 (2) | C16—C17 | 1.402 (3) |
| O8—C11 | 1.281 (2) | C16—H16 | 0.9300 |
| O9—C14 | 1.230 (3) | C17—C23 | 1.393 (3) |
| O10—C14 | 1.291 (3) | C17—C18 | 1.487 (3) |
| O11—H11A | 0.8500 | C18—C22 | 1.397 (3) |
| O13—H13B | 0.8499 | C18—C19 | 1.399 (3) |
| O13—H13A | 0.8500 | C19—C20 | 1.378 (3) |
| O15—H15B | 0.8500 | C19—H19 | 0.9300 |
| O15—H15A | 0.8501 | C20—H20 | 0.9300 |
| O16—H16A | 0.8549 | C21—C22 | 1.383 (3) |
| N1—C2 | 1.348 (2) | C21—H21 | 0.9300 |
| N1—C6 | 1.350 (3) | C22—H22 | 0.9300 |
| N2—C9 | 1.347 (3) | C23—C24 | 1.381 (3) |
| N2—C13 | 1.353 (3) | C23—H23 | 0.9300 |
| N3—C21 | 1.336 (3) | C24—H24 | 0.9300 |
| N3—C20 | 1.342 (3) | ||
| O11—Sb1—O1 | 88.73 (6) | C2—C3—C4 | 120.02 (18) |
| O11—Sb1—N1 | 87.40 (6) | C2—C3—H3 | 120.0 |
| O1—Sb1—N1 | 72.28 (6) | C4—C3—H3 | 120.0 |
| O11—Sb1—O5 | 82.88 (6) | O3—C4—C3 | 122.05 (18) |
| O1—Sb1—O5 | 141.44 (5) | O3—C4—C5 | 122.18 (19) |
| N1—Sb1—O5 | 69.80 (6) | C3—C4—C5 | 115.77 (18) |
| O11—Sb1—O13 | 79.47 (7) | C6—C5—C4 | 120.04 (19) |
| O1—Sb1—O13 | 72.89 (5) | C6—C5—H5 | 120.0 |
| N1—Sb1—O13 | 142.91 (6) | C4—C5—H5 | 120.0 |
| O5—Sb1—O13 | 140.84 (5) | N1—C6—C5 | 122.63 (18) |
| O11—Sb1—O10 | 78.80 (5) | N1—C6—C7 | 113.70 (17) |
| O1—Sb1—O10 | 148.04 (5) | C5—C6—C7 | 123.67 (18) |
| N1—Sb1—O10 | 135.33 (5) | O4—C7—O5 | 125.85 (18) |
| O5—Sb1—O10 | 66.46 (5) | O4—C7—C6 | 119.32 (18) |
| O13—Sb1—O10 | 75.93 (5) | O5—C7—C6 | 114.82 (17) |
| O16—Sb2—O6 | 84.67 (6) | O7—C8—O6 | 123.94 (19) |
| O16—Sb2—N2 | 89.44 (6) | O7—C8—C9 | 121.27 (18) |
| O6—Sb2—N2 | 72.66 (6) | O6—C8—C9 | 114.78 (17) |
| O16—Sb2—O10 | 87.61 (6) | N2—C9—C10 | 122.26 (19) |
| O6—Sb2—O10 | 141.57 (5) | N2—C9—C8 | 112.91 (17) |
| N2—Sb2—O10 | 69.67 (6) | C10—C9—C8 | 124.82 (18) |
| O16—Sb2—O15 | 84.54 (6) | C9—C10—C11 | 120.29 (18) |
| O6—Sb2—O15 | 74.52 (5) | C9—C10—H10 | 119.9 |
| N2—Sb2—O15 | 147.04 (6) | C11—C10—H10 | 119.9 |
| O10—Sb2—O15 | 142.00 (5) | O8—C11—C10 | 122.67 (18) |
| O16—Sb2—O5 | 73.88 (5) | O8—C11—C12 | 121.74 (18) |
| O6—Sb2—O5 | 145.16 (5) | C10—C11—C12 | 115.58 (18) |
| N2—Sb2—O5 | 132.68 (5) | C13—C12—C11 | 120.15 (19) |
| O10—Sb2—O5 | 65.76 (5) | C13—C12—H12 | 119.9 |
| O15—Sb2—O5 | 76.35 (5) | C11—C12—H12 | 119.9 |
| H1A—O1W—H1B | 108.1 | N2—C13—C12 | 122.65 (18) |
| C1—O1—Sb1 | 120.34 (13) | N2—C13—C14 | 113.87 (17) |
| H2A—O2W—H2B | 107.6 | C12—C13—C14 | 123.48 (18) |
| C7—O5—Sb1 | 118.75 (12) | O9—C14—O10 | 125.98 (19) |
| C7—O5—Sb2 | 127.75 (12) | O9—C14—C13 | 119.46 (18) |
| Sb1—O5—Sb2 | 113.14 (6) | O10—C14—C13 | 114.56 (17) |
| C8—O6—Sb2 | 120.80 (13) | N4—C15—C16 | 120.29 (19) |
| C14—O10—Sb2 | 118.36 (12) | N4—C15—H15 | 119.9 |
| C14—O10—Sb1 | 127.57 (12) | C16—C15—H15 | 119.9 |
| Sb2—O10—Sb1 | 114.08 (5) | C15—C16—C17 | 119.5 (2) |
| Sb1—O11—H11A | 108.5 | C15—C16—H16 | 120.2 |
| Sb1—O13—H13B | 138.7 | C17—C16—H16 | 120.2 |
| Sb1—O13—H13A | 103.0 | C23—C17—C16 | 118.27 (18) |
| H13B—O13—H13A | 103.5 | C23—C17—C18 | 120.70 (19) |
| Sb2—O15—H15B | 137.7 | C16—C17—C18 | 121.00 (19) |
| Sb2—O15—H15A | 103.5 | C22—C18—C19 | 118.02 (18) |
| H15B—O15—H15A | 99.8 | C22—C18—C17 | 120.69 (19) |
| Sb2—O16—H16A | 113.5 | C19—C18—C17 | 121.29 (19) |
| C2—N1—C6 | 119.08 (17) | C20—C19—C18 | 119.8 (2) |
| C2—N1—Sb1 | 118.77 (13) | C20—C19—H19 | 120.1 |
| C6—N1—Sb1 | 122.11 (13) | C18—C19—H19 | 120.1 |
| C9—N2—C13 | 119.02 (17) | N3—C20—C19 | 120.3 (2) |
| C9—N2—Sb2 | 118.66 (13) | N3—C20—H20 | 119.9 |
| C13—N2—Sb2 | 122.29 (13) | C19—C20—H20 | 119.9 |
| C21—N3—C20 | 121.90 (18) | N3—C21—C22 | 120.11 (19) |
| C21—N3—H3A | 116.7 | N3—C21—H21 | 119.9 |
| C20—N3—H3A | 121.4 | C22—C21—H21 | 119.9 |
| C15—N4—C24 | 121.93 (18) | C21—C22—C18 | 119.90 (19) |
| C15—N4—H4A | 115.0 | C21—C22—H22 | 120.0 |
| C24—N4—H4A | 123.1 | C18—C22—H22 | 120.0 |
| O2—C1—O1 | 123.94 (19) | C24—C23—C17 | 119.90 (19) |
| O2—C1—C2 | 121.16 (19) | C24—C23—H23 | 120.0 |
| O1—C1—C2 | 114.88 (17) | C17—C23—H23 | 120.0 |
| N1—C2—C3 | 122.44 (19) | N4—C24—C23 | 120.1 (2) |
| N1—C2—C1 | 113.16 (17) | N4—C24—H24 | 120.0 |
| C3—C2—C1 | 124.39 (18) | C23—C24—H24 | 120.0 |
| O11—Sb1—O1—C1 | −94.49 (15) | Sb1—N1—C2—C1 | −0.4 (2) |
| N1—Sb1—O1—C1 | −6.82 (14) | O2—C1—C2—N1 | 173.49 (19) |
| O5—Sb1—O1—C1 | −17.6 (2) | O1—C1—C2—N1 | −5.3 (3) |
| O13—Sb1—O1—C1 | −173.86 (16) | O2—C1—C2—C3 | −5.3 (3) |
| O10—Sb1—O1—C1 | −160.75 (13) | O1—C1—C2—C3 | 175.91 (19) |
| O11—Sb1—O5—C7 | 98.21 (15) | N1—C2—C3—C4 | −0.9 (3) |
| O1—Sb1—O5—C7 | 19.31 (19) | C1—C2—C3—C4 | 177.82 (19) |
| N1—Sb1—O5—C7 | 8.37 (14) | C2—C3—C4—O3 | −179.9 (2) |
| O13—Sb1—O5—C7 | 161.79 (14) | C2—C3—C4—C5 | 0.5 (3) |
| O10—Sb1—O5—C7 | 179.06 (16) | O3—C4—C5—C6 | −179.3 (2) |
| O11—Sb1—O5—Sb2 | −75.41 (7) | C3—C4—C5—C6 | 0.2 (3) |
| O1—Sb1—O5—Sb2 | −154.31 (7) | C2—N1—C6—C5 | 0.4 (3) |
| N1—Sb1—O5—Sb2 | −165.25 (8) | Sb1—N1—C6—C5 | −177.52 (15) |
| O13—Sb1—O5—Sb2 | −11.83 (12) | C2—N1—C6—C7 | −178.94 (17) |
| O10—Sb1—O5—Sb2 | 5.44 (4) | Sb1—N1—C6—C7 | 3.1 (2) |
| O16—Sb2—O5—C7 | 85.91 (16) | C4—C5—C6—N1 | −0.7 (3) |
| O6—Sb2—O5—C7 | 31.7 (2) | C4—C5—C6—C7 | 178.54 (18) |
| N2—Sb2—O5—C7 | 159.63 (15) | Sb1—O5—C7—O4 | 171.21 (16) |
| O10—Sb2—O5—C7 | −179.36 (17) | Sb2—O5—C7—O4 | −16.2 (3) |
| O15—Sb2—O5—C7 | −2.28 (15) | Sb1—O5—C7—C6 | −9.6 (2) |
| O16—Sb2—O5—Sb1 | −101.17 (7) | Sb2—O5—C7—C6 | 163.02 (12) |
| O6—Sb2—O5—Sb1 | −155.40 (7) | N1—C6—C7—O4 | −176.23 (18) |
| N2—Sb2—O5—Sb1 | −27.44 (10) | C5—C6—C7—O4 | 4.4 (3) |
| O10—Sb2—O5—Sb1 | −6.43 (5) | N1—C6—C7—O5 | 4.5 (3) |
| O15—Sb2—O5—Sb1 | 170.65 (7) | C5—C6—C7—O5 | −174.85 (19) |
| O16—Sb2—O6—C8 | 95.22 (15) | Sb2—O6—C8—O7 | 174.97 (16) |
| N2—Sb2—O6—C8 | 4.14 (15) | Sb2—O6—C8—C9 | −4.5 (2) |
| O10—Sb2—O6—C8 | 15.9 (2) | C13—N2—C9—C10 | 0.6 (3) |
| O15—Sb2—O6—C8 | −178.98 (16) | Sb2—N2—C9—C10 | −177.32 (15) |
| O5—Sb2—O6—C8 | 146.75 (13) | C13—N2—C9—C8 | 179.79 (17) |
| O16—Sb2—O10—C14 | −100.59 (15) | Sb2—N2—C9—C8 | 1.8 (2) |
| O6—Sb2—O10—C14 | −22.27 (19) | O7—C8—C9—N2 | −177.86 (19) |
| N2—Sb2—O10—C14 | −10.30 (14) | O6—C8—C9—N2 | 1.6 (3) |
| O15—Sb2—O10—C14 | −178.59 (13) | O7—C8—C9—C10 | 1.3 (3) |
| O5—Sb2—O10—C14 | −173.98 (16) | O6—C8—C9—C10 | −179.23 (19) |
| O16—Sb2—O10—Sb1 | 78.87 (7) | N2—C9—C10—C11 | 1.2 (3) |
| O6—Sb2—O10—Sb1 | 157.19 (7) | C8—C9—C10—C11 | −177.87 (18) |
| N2—Sb2—O10—Sb1 | 169.16 (8) | C9—C10—C11—O8 | 177.21 (19) |
| O15—Sb2—O10—Sb1 | 0.88 (11) | C9—C10—C11—C12 | −2.1 (3) |
| O5—Sb2—O10—Sb1 | 5.48 (5) | O8—C11—C12—C13 | −177.93 (19) |
| O11—Sb1—O10—C14 | −100.08 (17) | C10—C11—C12—C13 | 1.4 (3) |
| O1—Sb1—O10—C14 | −31.2 (2) | C9—N2—C13—C12 | −1.4 (3) |
| N1—Sb1—O10—C14 | −174.64 (15) | Sb2—N2—C13—C12 | 176.48 (15) |
| O5—Sb1—O10—C14 | 172.88 (17) | C9—N2—C13—C14 | 178.68 (17) |
| O13—Sb1—O10—C14 | −18.26 (16) | Sb2—N2—C13—C14 | −3.4 (2) |
| O11—Sb1—O10—Sb2 | 80.52 (7) | C11—C12—C13—N2 | 0.3 (3) |
| O1—Sb1—O10—Sb2 | 149.42 (8) | C11—C12—C13—C14 | −179.77 (18) |
| N1—Sb1—O10—Sb2 | 5.96 (11) | Sb2—O10—C14—O9 | −168.47 (18) |
| O5—Sb1—O10—Sb2 | −6.53 (5) | Sb1—O10—C14—O9 | 12.2 (3) |
| O13—Sb1—O10—Sb2 | 162.33 (8) | Sb2—O10—C14—C13 | 12.0 (2) |
| O11—Sb1—N1—C2 | 92.96 (15) | Sb1—O10—C14—C13 | −167.43 (12) |
| O1—Sb1—N1—C2 | 3.46 (14) | N2—C13—C14—O9 | 174.43 (19) |
| O5—Sb1—N1—C2 | 176.33 (16) | C12—C13—C14—O9 | −5.5 (3) |
| O13—Sb1—N1—C2 | 24.3 (2) | N2—C13—C14—O10 | −6.0 (3) |
| O10—Sb1—N1—C2 | 164.14 (12) | C12—C13—C14—O10 | 174.13 (19) |
| O11—Sb1—N1—C6 | −89.12 (16) | C24—N4—C15—C16 | −0.7 (3) |
| O1—Sb1—N1—C6 | −178.62 (17) | N4—C15—C16—C17 | 1.2 (3) |
| O5—Sb1—N1—C6 | −5.75 (14) | C15—C16—C17—C23 | −0.9 (3) |
| O13—Sb1—N1—C6 | −157.80 (14) | C15—C16—C17—C18 | 177.29 (19) |
| O10—Sb1—N1—C6 | −17.93 (19) | C23—C17—C18—C22 | −23.5 (3) |
| O16—Sb2—N2—C9 | −87.61 (15) | C16—C17—C18—C22 | 158.33 (19) |
| O6—Sb2—N2—C9 | −3.03 (14) | C23—C17—C18—C19 | 156.3 (2) |
| O10—Sb2—N2—C9 | −175.27 (16) | C16—C17—C18—C19 | −21.9 (3) |
| O15—Sb2—N2—C9 | −8.6 (2) | C22—C18—C19—C20 | 0.6 (3) |
| O5—Sb2—N2—C9 | −154.87 (13) | C17—C18—C19—C20 | −179.2 (2) |
| O16—Sb2—N2—C13 | 94.50 (16) | C21—N3—C20—C19 | −0.8 (3) |
| O6—Sb2—N2—C13 | 179.08 (17) | C18—C19—C20—N3 | 0.0 (3) |
| O10—Sb2—N2—C13 | 6.84 (14) | C20—N3—C21—C22 | 0.9 (3) |
| O15—Sb2—N2—C13 | 173.56 (13) | N3—C21—C22—C18 | −0.2 (3) |
| O5—Sb2—N2—C13 | 27.24 (18) | C19—C18—C22—C21 | −0.5 (3) |
| Sb1—O1—C1—O2 | −169.95 (16) | C17—C18—C22—C21 | 179.29 (19) |
| Sb1—O1—C1—C2 | 8.8 (2) | C16—C17—C23—C24 | 0.2 (3) |
| C6—N1—C2—C3 | 0.4 (3) | C18—C17—C23—C24 | −178.03 (19) |
| Sb1—N1—C2—C3 | 178.41 (15) | C15—N4—C24—C23 | −0.1 (3) |
| C6—N1—C2—C1 | −178.42 (17) | C17—C23—C24—N4 | 0.3 (3) |
| H··· | ||||
| O1W—H1A···O2i | 0.85 | 1.88 | 2.725 (2) | 177 |
| O1W—H1B···O11ii | 0.85 | 1.87 | 2.704 (2) | 167 |
| O2W—H2A···O7iii | 0.86 | 1.85 | 2.703 (2) | 171 |
| O2W—H2B···O16iv | 0.85 | 1.86 | 2.669 (2) | 157 |
| O11—H11A···O2W | 0.85 | 1.90 | 2.688 (2) | 154 |
| O16—H16A···O1W | 0.85 | 1.88 | 2.684 (2) | 155 |
| O13—H13A···O9 | 0.85 | 1.83 | 2.672 (2) | 173 |
| O13—H13B···O3v | 0.85 | 1.92 | 2.764 (2) | 173 |
| O15—H15A···O4 | 0.85 | 1.88 | 2.709 (2) | 166 |
| O15—H15B···O8vi | 0.85 | 1.98 | 2.823 (2) | 171 |
| N3—H3A···O3vii | 0.85 | 1.78 | 2.624 (2) | 171 |
| N4—H4A···O8vi | 0.85 | 1.80 | 2.648 (2) | 173 |
| C3—H3···O1Wi | 0.93 | 2.60 | 3.460 (3) | 154 |
| C5—H5···O9vi | 0.93 | 2.53 | 3.434 (3) | 164 |
| C12—H12···O4v | 0.93 | 2.55 | 3.470 (3) | 172 |
| C15—H15···O6 | 0.93 | 2.59 | 3.415 (3) | 149 |
| C19—H19···O2Wiii | 0.93 | 2.60 | 3.484 (3) | 160 |
| C20—H20···O1Wviii | 0.93 | 2.25 | 3.172 (3) | 172 |
| C21—H21···O1ix | 0.93 | 2.44 | 3.358 (3) | 170 |
| C22—H22···O2ix | 0.93 | 2.45 | 3.107 (3) | 128 |
| C24—H24···O16x | 0.93 | 2.57 | 3.261 (3) | 131 |
Hydrogen-bond geometry (Å, °)
| H⋯ | ||||
|---|---|---|---|---|
| O1 | 0.85 | 1.88 | 2.725 (2) | 177 |
| O1 | 0.85 | 1.87 | 2.704 (2) | 167 |
| O2 | 0.86 | 1.85 | 2.703 (2) | 171 |
| O2 | 0.85 | 1.86 | 2.669 (2) | 157 |
| O11—H11 | 0.85 | 1.90 | 2.688 (2) | 154 |
| O16—H16 | 0.85 | 1.88 | 2.684 (2) | 155 |
| O13—H13 | 0.85 | 1.83 | 2.672 (2) | 173 |
| O13—H13 | 0.85 | 1.92 | 2.764 (2) | 173 |
| O15—H15 | 0.85 | 1.88 | 2.709 (2) | 166 |
| O15—H15 | 0.85 | 1.98 | 2.823 (2) | 171 |
| N3—H3 | 0.85 | 1.78 | 2.624 (2) | 171 |
| N4—H4 | 0.85 | 1.80 | 2.648 (2) | 173 |
| C3—H3⋯O1 | 0.93 | 2.60 | 3.460 (3) | 154 |
| C5—H5⋯O9vi | 0.93 | 2.53 | 3.434 (3) | 164 |
| C12—H12⋯O4v | 0.93 | 2.55 | 3.470 (3) | 172 |
| C15—H15⋯O6 | 0.93 | 2.59 | 3.415 (3) | 149 |
| C19—H19⋯O2 | 0.93 | 2.60 | 3.484 (3) | 160 |
| C20—H20⋯O1 | 0.93 | 2.25 | 3.172 (3) | 172 |
| C21—H21⋯O1ix | 0.93 | 2.44 | 3.358 (3) | 170 |
| C22—H22⋯O2ix | 0.93 | 2.45 | 3.107 (3) | 128 |
| C24—H24⋯O16x | 0.93 | 2.57 | 3.261 (3) | 131 |
Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) ; (ix) ; (x) .