| Literature DB >> 21836845 |
Iran Sheikhshoaie, Vratislav Langer, Seyed Ali Yasrebi.
Abstract
In the title benzil-idene Schiff baseEntities:
Year: 2011 PMID: 21836845 PMCID: PMC3152014 DOI: 10.1107/S1600536811020101
Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN: 1600-5368
| [Mo(C15H12N2O3)O2(CH4O)] | |
| Monoclinic, | Mo |
| Hall symbol: -C 2yc | Cell parameters from 5066 reflections |
| θ = 2.5–32.3° | |
| µ = 0.82 mm−1 | |
| β = 112.993 (8)° | Block, orange |
| 0.58 × 0.54 × 0.46 mm | |
| Bruker SMART CCD diffractometer | 5867 independent reflections |
| Radiation source: fine-focus sealed tube | 4401 reflections with |
| graphite | |
| ω scans | θmax = 32.8°, θmin = 2.5° |
| Absorption correction: multi-scan ( | |
| 27788 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 | |
| 5867 reflections | (Δ/σ)max = 0.001 |
| 229 parameters | Δρmax = 1.38 e Å−3 |
| 0 restraints | Δρmin = −1.80 e Å−3 |
| Experimental. Data were collected at 173 K using a Siemens |
| 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 |
| Mo1 | 0.169567 (7) | 0.55438 (2) | 0.093970 (13) | 0.01640 (7) | |
| O1 | 0.23804 (6) | 0.54087 (18) | 0.09191 (12) | 0.0191 (3) | |
| O2 | 0.11949 (6) | 0.47242 (19) | 0.13716 (13) | 0.0209 (3) | |
| O3 | 0.02944 (7) | 0.4772 (2) | 0.13247 (15) | 0.0299 (4) | |
| O4 | 0.17354 (6) | 0.74754 (19) | 0.12674 (13) | 0.0244 (4) | |
| O5 | 0.13736 (7) | 0.5485 (2) | −0.03385 (13) | 0.0254 (4) | |
| N1 | 0.19324 (7) | 0.3025 (2) | 0.11307 (13) | 0.0163 (3) | |
| N2 | 0.24201 (7) | 0.2753 (2) | 0.12187 (14) | 0.0176 (4) | |
| C1 | 0.11885 (8) | 0.1902 (3) | 0.12040 (16) | 0.0185 (4) | |
| C2 | 0.09645 (8) | 0.3331 (3) | 0.12693 (16) | 0.0187 (4) | |
| C3 | 0.04804 (9) | 0.3332 (3) | 0.12641 (17) | 0.0226 (4) | |
| C4 | 0.02337 (9) | 0.1919 (3) | 0.11911 (19) | 0.0285 (5) | |
| H4 | −0.0093 | 0.1918 | 0.1170 | 0.034* | |
| C5 | 0.04618 (10) | 0.0501 (3) | 0.1148 (2) | 0.0282 (5) | |
| H5 | 0.0291 | −0.0456 | 0.1111 | 0.034* | |
| C6 | 0.09347 (9) | 0.0485 (3) | 0.11585 (19) | 0.0236 (5) | |
| H6 | 0.1089 | −0.0482 | 0.1135 | 0.028* | |
| C7 | 0.16837 (8) | 0.1801 (3) | 0.12059 (16) | 0.0189 (4) | |
| H7 | 0.1832 | 0.0799 | 0.1264 | 0.023* | |
| C8 | −0.02257 (10) | 0.4859 (4) | 0.1098 (2) | 0.0357 (6) | |
| H8A | −0.0409 | 0.4339 | 0.0452 | 0.054* | |
| H8B | −0.0327 | 0.5958 | 0.1053 | 0.054* | |
| H8C | −0.0297 | 0.4340 | 0.1633 | 0.054* | |
| C9 | 0.26226 (8) | 0.4068 (3) | 0.11017 (16) | 0.0171 (4) | |
| C10 | 0.31418 (8) | 0.4117 (3) | 0.11898 (17) | 0.0186 (4) | |
| C11 | 0.33256 (9) | 0.5503 (3) | 0.09429 (18) | 0.0212 (4) | |
| H11 | 0.3115 | 0.6383 | 0.0706 | 0.025* | |
| C12 | 0.38163 (10) | 0.5592 (3) | 0.1044 (2) | 0.0265 (5) | |
| H12 | 0.3938 | 0.6532 | 0.0874 | 0.032* | |
| C13 | 0.41308 (10) | 0.4306 (3) | 0.1396 (2) | 0.0279 (5) | |
| H13 | 0.4466 | 0.4370 | 0.1470 | 0.033* | |
| C14 | 0.39471 (9) | 0.2927 (3) | 0.1637 (2) | 0.0277 (5) | |
| H14 | 0.4158 | 0.2048 | 0.1873 | 0.033* | |
| C15 | 0.34575 (9) | 0.2829 (3) | 0.15337 (18) | 0.0228 (5) | |
| H15 | 0.3336 | 0.1883 | 0.1697 | 0.027* | |
| O1M | 0.21855 (6) | 0.51974 (19) | 0.26524 (12) | 0.0200 (3) | |
| H1M | 0.2288 | 0.6039 | 0.2964 | 0.030* | |
| C1M | 0.21418 (10) | 0.4038 (3) | 0.33394 (17) | 0.0240 (5) | |
| H1AM | 0.2338 | 0.4359 | 0.4035 | 0.036* | |
| H1BM | 0.2263 | 0.3030 | 0.3206 | 0.036* | |
| H1CM | 0.1794 | 0.3935 | 0.3244 | 0.036* |
| Mo1 | 0.01570 (10) | 0.01803 (10) | 0.01522 (9) | 0.00265 (7) | 0.00577 (7) | 0.00205 (7) |
| O1 | 0.0194 (8) | 0.0192 (8) | 0.0205 (7) | 0.0034 (6) | 0.0098 (6) | 0.0041 (6) |
| O2 | 0.0171 (8) | 0.0222 (8) | 0.0249 (8) | 0.0010 (6) | 0.0099 (7) | −0.0004 (6) |
| O3 | 0.0191 (9) | 0.0358 (10) | 0.0363 (10) | 0.0057 (7) | 0.0126 (8) | 0.0020 (8) |
| O4 | 0.0271 (9) | 0.0205 (8) | 0.0273 (9) | 0.0058 (7) | 0.0126 (7) | 0.0045 (7) |
| O5 | 0.0224 (9) | 0.0332 (10) | 0.0186 (8) | 0.0054 (7) | 0.0058 (7) | 0.0033 (7) |
| N1 | 0.0156 (9) | 0.0190 (8) | 0.0143 (8) | 0.0003 (7) | 0.0058 (7) | −0.0004 (6) |
| N2 | 0.0152 (8) | 0.0213 (9) | 0.0167 (8) | 0.0019 (7) | 0.0066 (7) | −0.0006 (7) |
| C1 | 0.0159 (10) | 0.0238 (11) | 0.0145 (9) | −0.0014 (8) | 0.0046 (8) | −0.0003 (8) |
| C2 | 0.0159 (10) | 0.0254 (11) | 0.0138 (9) | 0.0005 (8) | 0.0047 (8) | 0.0019 (8) |
| C3 | 0.0163 (10) | 0.0308 (12) | 0.0197 (10) | 0.0008 (9) | 0.0060 (8) | 0.0007 (9) |
| C4 | 0.0172 (11) | 0.0400 (14) | 0.0291 (12) | −0.0050 (10) | 0.0099 (10) | 0.0022 (11) |
| C5 | 0.0220 (12) | 0.0321 (13) | 0.0308 (13) | −0.0080 (10) | 0.0107 (10) | −0.0001 (10) |
| C6 | 0.0212 (11) | 0.0248 (11) | 0.0234 (11) | −0.0041 (9) | 0.0074 (9) | −0.0007 (9) |
| C7 | 0.0177 (10) | 0.0217 (10) | 0.0163 (9) | 0.0008 (8) | 0.0055 (8) | 0.0000 (8) |
| C8 | 0.0194 (12) | 0.0552 (18) | 0.0344 (14) | 0.0113 (12) | 0.0125 (11) | 0.0076 (13) |
| C9 | 0.0184 (10) | 0.0207 (10) | 0.0115 (8) | 0.0011 (8) | 0.0050 (8) | −0.0002 (7) |
| C10 | 0.0181 (10) | 0.0236 (11) | 0.0154 (9) | −0.0003 (8) | 0.0079 (8) | −0.0022 (8) |
| C11 | 0.0208 (11) | 0.0233 (11) | 0.0209 (10) | 0.0015 (9) | 0.0095 (9) | 0.0031 (9) |
| C12 | 0.0248 (12) | 0.0288 (12) | 0.0285 (12) | −0.0037 (10) | 0.0133 (10) | 0.0024 (10) |
| C13 | 0.0198 (11) | 0.0356 (14) | 0.0304 (13) | −0.0017 (10) | 0.0120 (10) | −0.0005 (10) |
| C14 | 0.0214 (12) | 0.0304 (13) | 0.0335 (13) | 0.0034 (10) | 0.0130 (10) | 0.0012 (10) |
| C15 | 0.0205 (11) | 0.0228 (11) | 0.0280 (12) | 0.0021 (9) | 0.0128 (9) | 0.0023 (9) |
| O1M | 0.0241 (8) | 0.0205 (8) | 0.0152 (7) | −0.0036 (6) | 0.0076 (6) | −0.0017 (6) |
| C1M | 0.0307 (13) | 0.0247 (11) | 0.0149 (10) | 0.0001 (9) | 0.0071 (9) | 0.0027 (8) |
| Mo1—O1 | 2.0281 (19) | C6—H6 | 0.9500 |
| Mo1—O2 | 1.9391 (17) | C7—H7 | 0.9500 |
| Mo1—O4 | 1.7096 (18) | C8—H8A | 0.9800 |
| Mo1—O5 | 1.7093 (19) | C8—H8B | 0.9800 |
| Mo1—N1 | 2.248 (2) | C8—H8C | 0.9800 |
| Mo1—O1M | 2.3374 (18) | C9—C10 | 1.482 (3) |
| O1—C9 | 1.321 (3) | C10—C15 | 1.400 (3) |
| O2—C2 | 1.350 (3) | C10—C11 | 1.404 (3) |
| O3—C3 | 1.364 (3) | C11—C12 | 1.394 (4) |
| O3—C8 | 1.435 (3) | C11—H11 | 0.9500 |
| N1—C7 | 1.306 (3) | C12—C13 | 1.399 (4) |
| N1—N2 | 1.409 (3) | C12—H12 | 0.9500 |
| N2—C9 | 1.313 (3) | C13—C14 | 1.396 (4) |
| C1—C2 | 1.409 (3) | C13—H13 | 0.9500 |
| C1—C6 | 1.411 (3) | C14—C15 | 1.391 (3) |
| C1—C7 | 1.457 (3) | C14—H14 | 0.9500 |
| C2—C3 | 1.420 (3) | C15—H15 | 0.9500 |
| C3—C4 | 1.392 (4) | O1M—C1M | 1.441 (3) |
| C4—C5 | 1.399 (4) | O1M—H1M | 0.8400 |
| C4—H4 | 0.9500 | C1M—H1AM | 0.9800 |
| C5—C6 | 1.384 (4) | C1M—H1BM | 0.9800 |
| C5—H5 | 0.9500 | C1M—H1CM | 0.9800 |
| O4—Mo1—O5 | 105.93 (8) | N1—C7—H7 | 118.5 |
| O4—Mo1—O2 | 103.86 (8) | C1—C7—H7 | 118.5 |
| O5—Mo1—O2 | 99.42 (9) | O3—C8—H8A | 109.5 |
| O4—Mo1—O1 | 95.61 (7) | O3—C8—H8B | 109.5 |
| O5—Mo1—O1 | 96.80 (8) | H8A—C8—H8B | 109.5 |
| O2—Mo1—O1 | 150.03 (7) | O3—C8—H8C | 109.5 |
| O4—Mo1—N1 | 155.24 (8) | H8A—C8—H8C | 109.5 |
| O5—Mo1—N1 | 96.81 (7) | H8B—C8—H8C | 109.5 |
| O2—Mo1—N1 | 81.49 (7) | N2—C9—O1 | 122.2 (2) |
| O1—Mo1—N1 | 71.67 (6) | N2—C9—C10 | 121.1 (2) |
| C9—O1—Mo1 | 120.49 (14) | O1—C9—C10 | 116.7 (2) |
| C2—O2—Mo1 | 134.07 (14) | C15—C10—C11 | 119.1 (2) |
| C3—O3—C8 | 116.8 (2) | C15—C10—C9 | 121.7 (2) |
| C7—N1—N2 | 116.36 (18) | C11—C10—C9 | 119.2 (2) |
| C7—N1—Mo1 | 128.46 (15) | C12—C11—C10 | 120.3 (2) |
| N2—N1—Mo1 | 115.13 (13) | C12—C11—H11 | 119.9 |
| C9—N2—N1 | 110.11 (18) | C10—C11—H11 | 119.9 |
| C2—C1—C6 | 119.7 (2) | C11—C12—C13 | 120.4 (2) |
| C2—C1—C7 | 122.9 (2) | C11—C12—H12 | 119.8 |
| C6—C1—C7 | 117.3 (2) | C13—C12—H12 | 119.8 |
| O2—C2—C1 | 123.0 (2) | C14—C13—C12 | 119.3 (2) |
| O2—C2—C3 | 117.3 (2) | C14—C13—H13 | 120.4 |
| C1—C2—C3 | 119.6 (2) | C12—C13—H13 | 120.4 |
| O3—C3—C4 | 125.4 (2) | C15—C14—C13 | 120.6 (2) |
| O3—C3—C2 | 115.2 (2) | C15—C14—H14 | 119.7 |
| C4—C3—C2 | 119.4 (2) | C13—C14—H14 | 119.7 |
| C3—C4—C5 | 120.8 (2) | C14—C15—C10 | 120.4 (2) |
| C3—C4—H4 | 119.6 | C14—C15—H15 | 119.8 |
| C5—C4—H4 | 119.6 | C10—C15—H15 | 119.8 |
| C6—C5—C4 | 120.3 (2) | C1M—O1M—H1M | 109.5 |
| C6—C5—H5 | 119.9 | O1M—C1M—H1AM | 109.5 |
| C4—C5—H5 | 119.9 | O1M—C1M—H1BM | 109.5 |
| C5—C6—C1 | 120.2 (2) | H1AM—C1M—H1BM | 109.5 |
| C5—C6—H6 | 119.9 | O1M—C1M—H1CM | 109.5 |
| C1—C6—H6 | 119.9 | H1AM—C1M—H1CM | 109.5 |
| N1—C7—C1 | 123.0 (2) | H1BM—C1M—H1CM | 109.5 |
| O4—Mo1—O1—C9 | 152.56 (16) | O2—C2—C3—C4 | −178.1 (2) |
| O5—Mo1—O1—C9 | −100.61 (16) | C1—C2—C3—C4 | −0.2 (3) |
| O2—Mo1—O1—C9 | 21.8 (2) | O3—C3—C4—C5 | −179.1 (2) |
| N1—Mo1—O1—C9 | −5.67 (15) | C2—C3—C4—C5 | 1.6 (4) |
| O4—Mo1—O2—C2 | 174.04 (19) | C3—C4—C5—C6 | −1.2 (4) |
| O5—Mo1—O2—C2 | 64.9 (2) | C4—C5—C6—C1 | −0.6 (4) |
| O1—Mo1—O2—C2 | −56.9 (3) | C2—C1—C6—C5 | 1.9 (3) |
| N1—Mo1—O2—C2 | −30.6 (2) | C7—C1—C6—C5 | −179.6 (2) |
| O4—Mo1—N1—C7 | 120.7 (2) | N2—N1—C7—C1 | 175.46 (18) |
| O5—Mo1—N1—C7 | −82.56 (19) | Mo1—N1—C7—C1 | −1.8 (3) |
| O2—Mo1—N1—C7 | 15.99 (19) | C2—C1—C7—N1 | −9.5 (3) |
| O1—Mo1—N1—C7 | −177.5 (2) | C6—C1—C7—N1 | 172.0 (2) |
| O4—Mo1—N1—N2 | −56.6 (2) | N1—N2—C9—O1 | −0.6 (3) |
| O5—Mo1—N1—N2 | 100.14 (14) | N1—N2—C9—C10 | 178.14 (18) |
| O2—Mo1—N1—N2 | −161.31 (14) | Mo1—O1—C9—N2 | 5.8 (3) |
| O1—Mo1—N1—N2 | 5.20 (13) | Mo1—O1—C9—C10 | −173.01 (14) |
| C7—N1—N2—C9 | 178.27 (19) | N2—C9—C10—C15 | −8.8 (3) |
| Mo1—N1—N2—C9 | −4.1 (2) | O1—C9—C10—C15 | 170.0 (2) |
| Mo1—O2—C2—C1 | 30.2 (3) | N2—C9—C10—C11 | 172.5 (2) |
| Mo1—O2—C2—C3 | −151.97 (17) | O1—C9—C10—C11 | −8.6 (3) |
| C6—C1—C2—O2 | 176.2 (2) | C15—C10—C11—C12 | −0.3 (3) |
| C7—C1—C2—O2 | −2.2 (3) | C9—C10—C11—C12 | 178.3 (2) |
| C6—C1—C2—C3 | −1.5 (3) | C10—C11—C12—C13 | −0.2 (4) |
| C7—C1—C2—C3 | −179.9 (2) | C11—C12—C13—C14 | 0.5 (4) |
| C8—O3—C3—C4 | −12.9 (4) | C12—C13—C14—C15 | −0.3 (4) |
| C8—O3—C3—C2 | 166.5 (2) | C13—C14—C15—C10 | −0.3 (4) |
| O2—C2—C3—O3 | 2.5 (3) | C11—C10—C15—C14 | 0.5 (3) |
| C1—C2—C3—O3 | −179.6 (2) | C9—C10—C15—C14 | −178.1 (2) |
| H··· | ||||
| O1M—H1M···N2i | 0.84 | 1.87 | 2.700 (3) | 173 |
| C1M—H1BM···O1ii | 0.98 | 2.58 | 3.402 (3) | 141 |
| C6—H6···O4iii | 0.95 | 2.53 | 3.450 (3) | 162 |
| C11—H11···O1 | 0.95 | 2.44 | 2.767 (3) | 100 |
| C15—H15···O1Mii | 0.95 | 2.54 | 3.427 (3) | 156 |
| Cis-dioxo molybdenum complex | Mo=O | Mo-N | Mo–O(solv)1 | N—Mo=O | O=Mo=O | |
| [MoO2(bnms)(MeOH)I | 1.709 | 2.248 | 2.337 | 155.24 | 105.93 | |
| 1.709 | 96.81 | |||||
| [MoO2(sae)(MeOH)]a | 1.697 | 2.252 | 2.339 | 158.9 | 106.1 | |
| 1.704 | 94.2 | |||||
| [MoO2(cysS-OR)(MeOH)]b | 1.699 | 2.291 | 2.385 | 160.8 | 105.9 | |
| 1.709 | 92.5 | |||||
| [MoO2(hbhy)(EtOH)]c | 1.696 | 2.234 | 2.356 | 158.44 | 106.03 | |
| 1.699 | 93.84 | |||||
| [MoO2(doin)(MeOH)]d | 1.700 | 2.250 | 2.331 | 159.54 | 106.65 | |
| 1.714 | 93.16 | |||||
| [MoO2(hpmp)(MeOH)]e | 1.703 | 2.274 | 2.355 | 159.38 | 107.05 | |
| 1.709 | 93.07 | |||||
| [MoO2(hpemp)(MeOH)]f | 1.707 | 2.268 | 2.387 | 159.81 | 106.36 | |
| 1.699 | 93.53 | |||||
| [MoO2(moip)(MeOH)]g | 1.700 | 2.251 | 2.349 | 158.82 | 105.61 | |
| 1.702 | 95.01 | |||||
| [MoO2(ssh)(MeOH)]h | 1.692 | 2.234 | 2.349 | 157.6 | 106.4 | |
| 1.705 | 93.7 | |||||
| [MoO2(hmt)(MeOH)]i | 1.727 | 2.273 | 2.351 | 156.41 | 105.26 | |
| 1.704 | 95.29 | |||||
| MoO2(bhpd)(MeOH)j | 1.988 | 2.284 | 2.301 | 160.49 | 105.9 | |
| 1.717 | 90.93 |
| Complex | νs(Mo═O)1 | νs(Mo═O)2 | ν(C═N) | |
| [MoO2(bnms)(MeOH)I | 939 | 915 | 1627 | |
| [MoO2(sae)(MeOH)]a | 928 | 906 | 1641 | |
| [MoO2(cysS-OR)(MeOH)]b | 995 | 980 | 1626 | |
| [MoO2(hbhy)(EtOH)]c | - | - | - | |
| [MoO2(doin)(MeOH)]d | - | - | - | |
| [MoO2(hpmp)(MeOH)]e | 924 | 900 | 1638 | |
| [MoO2(hpemp)(MeOH)]f | 920 | 909 | 1638 | |
| [MoO2(moip)(MeOH)]g | - | - | - | |
| [MoO2(ssh)(MeOH)]h | 939 | 911 | 1637 | |
| [MoO2(hmt)(MeOH)]i | 932 | 901 | 1626 | |
| MoO2(bhpd)(MeOH)j | 939 | 914 | 1579 |
Selected geometric parameters (Å, °)
| Mo1—O1 | 2.0281 (19) |
| Mo1—O2 | 1.9391 (17) |
| Mo1—O4 | 1.7096 (18) |
| Mo1—O5 | 1.7093 (19) |
| Mo1—N1 | 2.248 (2) |
| Mo1—O1 | 2.3374 (18) |
Hydrogen-bond geometry (Å, °)
| H⋯ | ||||
|---|---|---|---|---|
| O1 | 0.84 | 1.87 | 2.700 (3) | 173 |
| C1 | 0.98 | 2.58 | 3.402 (3) | 141 |
| C6—H6⋯O4iii | 0.95 | 2.53 | 3.450 (3) | 162 |
| C11—H11⋯O1 | 0.95 | 2.44 | 2.767 (3) | 100 |
| C15—H15⋯O1 | 0.95 | 2.54 | 3.427 (3) | 156 |
Symmetry codes: (i) ; (ii) ; (iii) .