| Literature DB >> 21578446 |
V H H Surendra Babu, M Krishnaiah, G Syam Prasad, Rajni Kant.
Abstract
In the title compound, C(17)H(20)BrClNO(4)P, inter-molecular C-H⋯O and N-H⋯OEntities:
Year: 2009 PMID: 21578446 PMCID: PMC2971341 DOI: 10.1107/S1600536809043062
Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN: 1600-5368
| C17H20BrClNO4P | |
| Triclinic, | |
| Hall symbol: -P 1 | Mo |
| Cell parameters from 5846 reflections | |
| θ = 3.0–30.4° | |
| µ = 2.37 mm−1 | |
| α = 82.921 (13)° | |
| β = 80.372 (15)° | Rectangular, colorless |
| γ = 70.701 (16)° | 0.30 × 0.24 × 0.18 mm |
| Oxford Diffraction Xcalibur diffractometer | 5846 independent reflections |
| Radiation source: fine-focus sealed tube | 2891 reflections with |
| graphite | |
| ω–2θ scans | θmax = 30.4°, θmin = 3.0° |
| Absorption correction: multi-scan ( | |
| 12477 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 | |
| 5846 reflections | (Δ/σ)max < 0.001 |
| 226 parameters | Δρmax = 0.60 e Å−3 |
| 0 restraints | Δρmin = −0.54 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 |
| Br2 | 0.84116 (6) | 0.35425 (7) | 0.05533 (3) | 0.0831 (2) | |
| P1 | 0.10786 (13) | 0.17964 (11) | 0.33103 (6) | 0.0449 (2) | |
| Cl3 | −0.27410 (17) | 0.89126 (14) | 0.07732 (7) | 0.0780 (4) | |
| C14 | −0.2049 (4) | 0.7262 (4) | 0.3792 (2) | 0.0411 (7) | |
| C16 | 0.2724 (4) | 0.3699 (3) | 0.2163 (2) | 0.0376 (7) | |
| N4 | 0.0040 (4) | 0.4840 (3) | 0.3349 (2) | 0.0485 (7) | |
| H4 | 0.0234 | 0.4629 | 0.3927 | 0.058* | |
| O8 | −0.1765 (4) | 0.6665 (3) | 0.46936 (17) | 0.0567 (7) | |
| H8 | −0.2379 | 0.7304 | 0.5067 | 0.085* | |
| C9 | −0.1081 (4) | 0.6286 (4) | 0.3084 (2) | 0.0382 (7) | |
| C15 | 0.0895 (5) | 0.3672 (4) | 0.2688 (2) | 0.0423 (8) | |
| H15 | 0.0074 | 0.3829 | 0.2217 | 0.051* | |
| O5 | 0.2300 (4) | 0.1371 (3) | 0.40377 (17) | 0.0572 (7) | |
| C11 | −0.2492 (5) | 0.8281 (4) | 0.1956 (3) | 0.0502 (9) | |
| O6 | 0.1667 (4) | 0.0744 (3) | 0.24775 (18) | 0.0593 (7) | |
| C19 | 0.6080 (5) | 0.3641 (5) | 0.1206 (3) | 0.0524 (9) | |
| C10 | −0.1319 (4) | 0.6816 (4) | 0.2156 (2) | 0.0419 (8) | |
| H10 | −0.0691 | 0.6189 | 0.1669 | 0.050* | |
| O7 | −0.0912 (4) | 0.1837 (4) | 0.3670 (2) | 0.0753 (8) | |
| C17 | 0.3277 (5) | 0.3198 (4) | 0.1277 (2) | 0.0487 (8) | |
| H17 | 0.2498 | 0.2873 | 0.0994 | 0.058* | |
| C13 | −0.3194 (5) | 0.8713 (4) | 0.3567 (3) | 0.0537 (9) | |
| H13 | −0.3830 | 0.9349 | 0.4049 | 0.064* | |
| C18 | 0.4954 (5) | 0.3157 (5) | 0.0789 (2) | 0.0538 (9) | |
| H18 | 0.5308 | 0.2806 | 0.0187 | 0.065* | |
| C20 | 0.5580 (6) | 0.4167 (6) | 0.2087 (3) | 0.0685 (12) | |
| H20 | 0.6367 | 0.4491 | 0.2365 | 0.082* | |
| C12 | −0.3424 (5) | 0.9249 (4) | 0.2649 (3) | 0.0588 (10) | |
| H12 | −0.4188 | 1.0238 | 0.2503 | 0.071* | |
| C21 | 0.3876 (5) | 0.4210 (5) | 0.2563 (3) | 0.0581 (10) | |
| H21 | 0.3510 | 0.4587 | 0.3158 | 0.070* | |
| C22 | 0.1764 (8) | −0.0834 (5) | 0.2531 (3) | 0.0801 (14) | |
| H22A | 0.0584 | −0.0939 | 0.2786 | 0.096* | |
| H22B | 0.2633 | −0.1438 | 0.2948 | 0.096* | |
| C23 | 0.2321 (8) | −0.1402 (6) | 0.1596 (4) | 0.0888 (16) | |
| H23A | 0.2394 | −0.2471 | 0.1633 | 0.133* | |
| H23B | 0.3491 | −0.1299 | 0.1348 | 0.133* | |
| H23C | 0.1447 | −0.0812 | 0.1189 | 0.133* | |
| C24 | −0.1716 (7) | 0.1893 (7) | 0.4638 (4) | 0.0946 (17) | |
| H24A | −0.1842 | 0.0893 | 0.4873 | 0.114* | |
| H24B | −0.0929 | 0.2121 | 0.5011 | 0.114* | |
| C25 | −0.3443 (8) | 0.3037 (8) | 0.4734 (5) | 0.139 (3) | |
| H25A | −0.3946 | 0.3076 | 0.5388 | 0.208* | |
| H25B | −0.4236 | 0.2788 | 0.4386 | 0.208* | |
| H25C | −0.3319 | 0.4024 | 0.4495 | 0.208* |
| Br2 | 0.0512 (3) | 0.1413 (5) | 0.0571 (3) | −0.0336 (3) | −0.00024 (19) | −0.0086 (3) |
| P1 | 0.0521 (5) | 0.0414 (5) | 0.0367 (5) | −0.0119 (4) | 0.0040 (4) | −0.0078 (4) |
| Cl3 | 0.0924 (8) | 0.0726 (7) | 0.0466 (6) | 0.0013 (6) | −0.0128 (5) | 0.0068 (5) |
| C14 | 0.0396 (17) | 0.0430 (19) | 0.0380 (17) | −0.0091 (14) | −0.0025 (14) | −0.0076 (14) |
| C16 | 0.0396 (17) | 0.0295 (16) | 0.0382 (17) | −0.0026 (13) | −0.0092 (13) | −0.0004 (13) |
| N4 | 0.0571 (18) | 0.0409 (16) | 0.0337 (14) | 0.0050 (13) | −0.0057 (13) | −0.0092 (12) |
| O8 | 0.0659 (16) | 0.0500 (15) | 0.0417 (14) | 0.0012 (12) | −0.0063 (12) | −0.0128 (11) |
| C9 | 0.0331 (16) | 0.0372 (18) | 0.0404 (17) | −0.0076 (13) | 0.0013 (13) | −0.0060 (14) |
| C15 | 0.0479 (19) | 0.0409 (18) | 0.0328 (16) | −0.0046 (15) | −0.0060 (14) | −0.0085 (14) |
| O5 | 0.0761 (18) | 0.0456 (15) | 0.0406 (14) | −0.0071 (13) | −0.0073 (12) | −0.0033 (11) |
| C11 | 0.046 (2) | 0.053 (2) | 0.047 (2) | −0.0094 (17) | −0.0110 (16) | 0.0035 (17) |
| O6 | 0.0845 (19) | 0.0450 (15) | 0.0504 (15) | −0.0265 (13) | 0.0051 (13) | −0.0142 (12) |
| C19 | 0.0420 (19) | 0.065 (2) | 0.048 (2) | −0.0172 (17) | −0.0069 (16) | 0.0058 (18) |
| C10 | 0.0411 (18) | 0.0381 (18) | 0.0394 (18) | −0.0041 (14) | 0.0005 (14) | −0.0077 (14) |
| O7 | 0.0709 (19) | 0.092 (2) | 0.0655 (19) | −0.0371 (17) | 0.0143 (15) | −0.0151 (16) |
| C17 | 0.052 (2) | 0.062 (2) | 0.0355 (18) | −0.0195 (18) | −0.0062 (15) | −0.0102 (16) |
| C13 | 0.056 (2) | 0.041 (2) | 0.050 (2) | 0.0055 (17) | −0.0049 (17) | −0.0109 (16) |
| C18 | 0.054 (2) | 0.070 (3) | 0.0354 (18) | −0.0170 (19) | 0.0011 (16) | −0.0130 (17) |
| C20 | 0.061 (3) | 0.100 (3) | 0.054 (2) | −0.033 (2) | −0.007 (2) | −0.019 (2) |
| C12 | 0.056 (2) | 0.042 (2) | 0.065 (3) | 0.0038 (17) | −0.0085 (19) | −0.0071 (18) |
| C21 | 0.056 (2) | 0.079 (3) | 0.043 (2) | −0.022 (2) | −0.0002 (17) | −0.0222 (19) |
| C22 | 0.115 (4) | 0.065 (3) | 0.068 (3) | −0.048 (3) | 0.019 (3) | −0.023 (2) |
| C23 | 0.113 (4) | 0.074 (3) | 0.086 (4) | −0.040 (3) | 0.018 (3) | −0.042 (3) |
| C24 | 0.077 (3) | 0.105 (4) | 0.080 (3) | −0.023 (3) | 0.021 (3) | 0.015 (3) |
| C25 | 0.086 (4) | 0.154 (6) | 0.115 (5) | 0.015 (4) | 0.039 (4) | 0.002 (4) |
| Br2—C19 | 1.894 (4) | C10—H10 | 0.9300 |
| P1—O5 | 1.471 (3) | O7—C24 | 1.433 (6) |
| P1—O6 | 1.548 (3) | C17—C18 | 1.378 (5) |
| P1—O7 | 1.553 (3) | C17—H17 | 0.9300 |
| P1—C15 | 1.815 (3) | C13—C12 | 1.375 (5) |
| Cl3—C11 | 1.755 (4) | C13—H13 | 0.9300 |
| C14—O8 | 1.372 (4) | C18—H18 | 0.9300 |
| C14—C13 | 1.375 (5) | C20—C21 | 1.389 (6) |
| C14—C9 | 1.394 (4) | C20—H20 | 0.9300 |
| C16—C17 | 1.364 (5) | C12—H12 | 0.9300 |
| C16—C21 | 1.377 (5) | C21—H21 | 0.9300 |
| C16—C15 | 1.515 (5) | C22—C23 | 1.452 (6) |
| N4—C9 | 1.379 (4) | C22—H22A | 0.9700 |
| N4—C15 | 1.440 (4) | C22—H22B | 0.9700 |
| N4—H4 | 0.8600 | C23—H23A | 0.9600 |
| O8—H8 | 0.8200 | C23—H23B | 0.9600 |
| C9—C10 | 1.388 (4) | C23—H23C | 0.9600 |
| C15—H15 | 0.9800 | C24—C25 | 1.413 (7) |
| C11—C12 | 1.367 (5) | C24—H24A | 0.9700 |
| C11—C10 | 1.385 (5) | C24—H24B | 0.9700 |
| O6—C22 | 1.420 (5) | C25—H25A | 0.9600 |
| C19—C18 | 1.358 (5) | C25—H25B | 0.9600 |
| C19—C20 | 1.365 (6) | C25—H25C | 0.9600 |
| O5—P1—O6 | 115.61 (15) | C12—C13—C14 | 121.8 (3) |
| O5—P1—O7 | 115.13 (17) | C12—C13—H13 | 119.1 |
| O6—P1—O7 | 104.18 (16) | C14—C13—H13 | 119.1 |
| O5—P1—C15 | 114.15 (16) | C19—C18—C17 | 118.7 (3) |
| O6—P1—C15 | 100.95 (15) | C19—C18—H18 | 120.7 |
| O7—P1—C15 | 105.21 (17) | C17—C18—H18 | 120.7 |
| O8—C14—C13 | 124.4 (3) | C19—C20—C21 | 118.9 (4) |
| O8—C14—C9 | 115.3 (3) | C19—C20—H20 | 120.6 |
| C13—C14—C9 | 120.3 (3) | C21—C20—H20 | 120.6 |
| C17—C16—C21 | 118.2 (3) | C11—C12—C13 | 117.8 (3) |
| C17—C16—C15 | 120.3 (3) | C11—C12—H12 | 121.1 |
| C21—C16—C15 | 121.4 (3) | C13—C12—H12 | 121.1 |
| C9—N4—C15 | 122.0 (3) | C16—C21—C20 | 120.7 (3) |
| C9—N4—H4 | 119.0 | C16—C21—H21 | 119.6 |
| C15—N4—H4 | 119.0 | C20—C21—H21 | 119.6 |
| C14—O8—H8 | 109.5 | O6—C22—C23 | 109.5 (4) |
| N4—C9—C10 | 123.9 (3) | O6—C22—H22A | 109.8 |
| N4—C9—C14 | 117.9 (3) | C23—C22—H22A | 109.8 |
| C10—C9—C14 | 118.2 (3) | O6—C22—H22B | 109.8 |
| N4—C15—C16 | 115.6 (3) | C23—C22—H22B | 109.8 |
| N4—C15—P1 | 108.2 (2) | H22A—C22—H22B | 108.2 |
| C16—C15—P1 | 110.7 (2) | C22—C23—H23A | 109.5 |
| N4—C15—H15 | 107.4 | C22—C23—H23B | 109.5 |
| C16—C15—H15 | 107.4 | H23A—C23—H23B | 109.5 |
| P1—C15—H15 | 107.4 | C22—C23—H23C | 109.5 |
| C12—C11—C10 | 122.0 (3) | H23A—C23—H23C | 109.5 |
| C12—C11—Cl3 | 119.5 (3) | H23B—C23—H23C | 109.5 |
| C10—C11—Cl3 | 118.5 (3) | C25—C24—O7 | 110.6 (5) |
| C22—O6—P1 | 126.1 (3) | C25—C24—H24A | 109.5 |
| C18—C19—C20 | 121.5 (4) | O7—C24—H24A | 109.5 |
| C18—C19—Br2 | 119.0 (3) | C25—C24—H24B | 109.5 |
| C20—C19—Br2 | 119.6 (3) | O7—C24—H24B | 109.5 |
| C11—C10—C9 | 119.9 (3) | H24A—C24—H24B | 108.1 |
| C11—C10—H10 | 120.0 | C24—C25—H25A | 109.5 |
| C9—C10—H10 | 120.0 | C24—C25—H25B | 109.5 |
| C24—O7—P1 | 124.8 (3) | H25A—C25—H25B | 109.5 |
| C16—C17—C18 | 122.0 (3) | C24—C25—H25C | 109.5 |
| C16—C17—H17 | 119.0 | H25A—C25—H25C | 109.5 |
| C18—C17—H17 | 119.0 | H25B—C25—H25C | 109.5 |
| C15—N4—C9—C10 | −8.0 (5) | N4—C9—C10—C11 | 179.2 (3) |
| C15—N4—C9—C14 | 171.1 (3) | C14—C9—C10—C11 | 0.1 (5) |
| O8—C14—C9—N4 | 0.3 (4) | O5—P1—O7—C24 | 16.9 (4) |
| C13—C14—C9—N4 | −179.6 (3) | O6—P1—O7—C24 | 144.5 (4) |
| O8—C14—C9—C10 | 179.5 (3) | C15—P1—O7—C24 | −109.7 (4) |
| C13—C14—C9—C10 | −0.4 (5) | C21—C16—C17—C18 | 1.5 (5) |
| C9—N4—C15—C16 | 88.1 (4) | C15—C16—C17—C18 | −177.9 (3) |
| C9—N4—C15—P1 | −147.2 (3) | O8—C14—C13—C12 | −180.0 (4) |
| C17—C16—C15—N4 | −150.5 (3) | C9—C14—C13—C12 | −0.1 (6) |
| C21—C16—C15—N4 | 30.1 (4) | C20—C19—C18—C17 | −0.3 (6) |
| C17—C16—C15—P1 | 86.1 (3) | Br2—C19—C18—C17 | 178.5 (3) |
| C21—C16—C15—P1 | −93.3 (3) | C16—C17—C18—C19 | −0.4 (6) |
| O5—P1—C15—N4 | −65.4 (3) | C18—C19—C20—C21 | −0.2 (7) |
| O6—P1—C15—N4 | 169.9 (2) | Br2—C19—C20—C21 | −179.0 (3) |
| O7—P1—C15—N4 | 61.7 (3) | C10—C11—C12—C13 | −1.4 (6) |
| O5—P1—C15—C16 | 62.1 (3) | Cl3—C11—C12—C13 | 180.0 (3) |
| O6—P1—C15—C16 | −62.6 (3) | C14—C13—C12—C11 | 0.9 (6) |
| O7—P1—C15—C16 | −170.7 (2) | C17—C16—C21—C20 | −2.1 (6) |
| O5—P1—O6—C22 | 66.1 (4) | C15—C16—C21—C20 | 177.3 (4) |
| O7—P1—O6—C22 | −61.3 (4) | C19—C20—C21—C16 | 1.4 (7) |
| C15—P1—O6—C22 | −170.2 (4) | P1—O6—C22—C23 | 178.3 (3) |
| C12—C11—C10—C9 | 0.9 (6) | P1—O7—C24—C25 | 132.8 (5) |
| Cl3—C11—C10—C9 | 179.5 (3) |
| H··· | ||||
| N4—H4···O8i | 0.86 | 2.47 | 3.287 (4) | 159 |
| C24—H24A···O5ii | 0.97 | 2.53 | 3.472 (7) | 163 |
| O8—H8···O5i | 0.82 | 1.90 | 2.615 (4) | 145 |
| C15—H15···Br2iii | 0.98 | 2.99 | 3.945 (4) | 164 |
| N4—H4···O8 | 0.86 | 2.27 | 2.626 (4) | 104 |
Hydrogen-bond geometry (Å, °)
| H⋯ | ||||
|---|---|---|---|---|
| N4—H4⋯O8i | 0.86 | 2.47 | 3.287 (4) | 159 |
| C24—H24 | 0.97 | 2.53 | 3.472 (7) | 163 |
| O8—H8⋯O5i | 0.82 | 1.90 | 2.615 (4) | 145 |
| C15—H15⋯Br2iii | 0.98 | 2.99 | 3.945 (4) | 164 |
| N4—H4⋯O8 | 0.86 | 2.27 | 2.626 (4) | 104 |
Symmetry codes: (i) ; (ii) ; (iii) .