| Literature DB >> 21579542 |
Peter Grundt1, Kelsi A Douglas, Bogdana Krivogorsky, Victor N Nemykin.
Abstract
There are two independent mol-ecules in the asymmetric unit of the title compound, C(15)H(6)Cl(2)N(2)O(2). The conjugated four-ring system is essentially planar in each mol-ecule [maximum deviation = 0.089 (2) Å]. In the crystal, weak inter-molecular C-H⋯Cl, C-H⋯O and C-H⋯·N inter-actions help to stabilize the packing.Entities:
Year: 2010 PMID: 21579542 PMCID: PMC2979507 DOI: 10.1107/S1600536810018969
Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN: 1600-5368
| C15H6Cl2N2O2 | |
| Triclinic, | |
| Hall symbol: -P 1 | Melting point: 200 K |
| Mo | |
| Cell parameters from 28356 reflections | |
| θ = 3.1–27.5° | |
| α = 94.908 (7)° | µ = 0.54 mm−1 |
| β = 96.709 (7)° | |
| γ = 107.395 (8)° | Block, yellow |
| 0.54 × 0.48 × 0.35 mm |
| Rigaku R-AXIS RAPID-II imaging plate diffractometer | 5585 independent reflections |
| Radiation source: Sealed tube (Mo) | 4830 reflections with |
| graphite | |
| Detector resolution: 10 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
| ω scans | |
| Absorption correction: multi-scan ( | |
| 31502 measured reflections |
| Refinement on | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| All H-atom parameters refined | |
| Method = Modified Sheldrick
| |
| (Δ/σ)max = 0.001 | |
| 5571 reflections | Δρmax = 0.53 e Å−3 |
| 416 parameters | Δρmin = −0.36 e Å−3 |
| 84 restraints | Extinction correction: Larson (1970), Equation 22 |
| 0 constraints | Extinction coefficient: 43 (4) |
| Primary atom site location: structure-invariant direct methods |
| Experimental. The crystal was placed in the cold stream of an X-stream 2000 liquid nitrogen generator with open-flow nitrogen cryostat with a nominal stability of 0.1 K. 1H NMR (DMSO-d6, 500 MHz): d 7.75-7.78 (m, 2H), 7.98-8.00 (m, 2H), 8.33 (d, J 7.5, 1H), 8.41 (d, J 1.9, 1H). 13C NMR (DMSO-d6, 125 MHz): d 115.6, 118.3, 122.6, 127.0, 127.4, 129.9, 130.1, 132.3, 135.6, 141.6, 144.4, 146.1, 147.3, 157.6, 178.4. |
| Refinement. Crystals for Windows program eliminates all reflections with [Sin theta/lambda]**2 less than 0.01 in order to eliminate reflections that may be poorly measured in the vicinity of the beam stop. Such filter eliminated 14 reflections, which resulted in difference between 5585 measured unique reflections and 5571 reflections used for refinement. |
| Cl1A | 0.12767 (7) | 0.19849 (5) | −0.30745 (3) | 0.0154 | |
| Cl2A | 0.22470 (8) | −0.16786 (5) | −0.51632 (3) | 0.0203 | |
| O1A | 0.5092 (2) | 0.25603 (14) | −0.16905 (8) | 0.0172 | |
| O2A | 0.8111 (2) | −0.15104 (14) | −0.30107 (8) | 0.0181 | |
| C1A | 1.1319 (3) | −0.08669 (19) | −0.17069 (12) | 0.0162 | |
| C2A | 1.2819 (3) | −0.0485 (2) | −0.10617 (12) | 0.0183 | |
| C3A | 1.2850 (3) | 0.0523 (2) | −0.04843 (12) | 0.0208 | |
| C4A | 1.1391 (3) | 0.1145 (2) | −0.05462 (12) | 0.0185 | |
| N5A | 0.8403 (2) | 0.14280 (16) | −0.12490 (10) | 0.0151 | |
| C6A | 0.5402 (3) | 0.16629 (19) | −0.20790 (11) | 0.0137 | |
| C7A | 0.2640 (3) | 0.09548 (18) | −0.33341 (11) | 0.0137 | |
| C8A | 0.1974 (3) | 0.01396 (19) | −0.40464 (11) | 0.0154 | |
| C9A | 0.3055 (3) | −0.06961 (19) | −0.42595 (11) | 0.0151 | |
| C10A | 0.4729 (3) | −0.07980 (19) | −0.37831 (11) | 0.0146 | |
| N11A | 0.6952 (2) | 0.01079 (16) | −0.24828 (9) | 0.0130 | |
| C12A | 0.8273 (3) | −0.06404 (19) | −0.24787 (11) | 0.0140 | |
| C13A | 0.9855 (3) | 0.07665 (19) | −0.11960 (11) | 0.0142 | |
| C14A | 0.7090 (3) | 0.10816 (18) | −0.18691 (11) | 0.0134 | |
| C15A | 0.4331 (3) | 0.09159 (18) | −0.28464 (11) | 0.0129 | |
| C16A | 0.5321 (3) | 0.00196 (19) | −0.30772 (11) | 0.0141 | |
| C17A | 0.9828 (3) | −0.02472 (18) | −0.17809 (11) | 0.0139 | |
| Cl1B | 0.89170 (7) | 0.34858 (5) | 0.34019 (3) | 0.0173 | |
| Cl2B | 0.70190 (7) | 0.70635 (5) | 0.52404 (3) | 0.0192 | |
| O1B | 0.5337 (2) | 0.26130 (14) | 0.19080 (9) | 0.0189 | |
| O2B | 0.1512 (2) | 0.64871 (14) | 0.28391 (8) | 0.0169 | |
| C1B | −0.1458 (3) | 0.55847 (19) | 0.14382 (12) | 0.0163 | |
| C2B | −0.2819 (3) | 0.5080 (2) | 0.07583 (12) | 0.0193 | |
| C3B | −0.2635 (3) | 0.4038 (2) | 0.02547 (12) | 0.0192 | |
| C4B | −0.1086 (3) | 0.3521 (2) | 0.04302 (12) | 0.0176 | |
| N5B | 0.1872 (3) | 0.34718 (16) | 0.12667 (10) | 0.0153 | |
| C6B | 0.4831 (3) | 0.34864 (19) | 0.22288 (11) | 0.0148 | |
| C7B | 0.7333 (3) | 0.44170 (19) | 0.35489 (12) | 0.0146 | |
| C8B | 0.7737 (3) | 0.5271 (2) | 0.42418 (12) | 0.0165 | |
| C9B | 0.6463 (3) | 0.60188 (19) | 0.43630 (11) | 0.0151 | |
| C10B | 0.4808 (3) | 0.59806 (19) | 0.38219 (11) | 0.0144 | |
| N11B | 0.2930 (2) | 0.49043 (16) | 0.24801 (9) | 0.0130 | |
| C12B | 0.1523 (3) | 0.55777 (19) | 0.23644 (11) | 0.0138 | |
| C13B | 0.0312 (3) | 0.40238 (18) | 0.11173 (11) | 0.0139 | |
| C14B | 0.3049 (3) | 0.39217 (19) | 0.19191 (11) | 0.0140 | |
| C15B | 0.5689 (3) | 0.43274 (19) | 0.29911 (11) | 0.0139 | |
| C16B | 0.4478 (3) | 0.51304 (19) | 0.31342 (11) | 0.0135 | |
| C17B | 0.0111 (3) | 0.50602 (19) | 0.16292 (11) | 0.0141 | |
| H1A | 1.130 (2) | −0.1539 (13) | −0.2094 (9) | 0.0204* | |
| H2A | 1.380 (2) | −0.0909 (13) | −0.1021 (9) | 0.0206* | |
| H3A | 1.388 (2) | 0.0793 (14) | −0.0051 (9) | 0.0251* | |
| H4A | 1.142 (2) | 0.1815 (13) | −0.0153 (9) | 0.0215* | |
| H5A | 0.083 (2) | 0.0145 (13) | −0.4368 (9) | 0.0178* | |
| H6A | 0.541 (2) | −0.1385 (13) | −0.3938 (9) | 0.0187* | |
| H1B | −0.159 (2) | 0.6286 (13) | 0.1773 (9) | 0.0204* | |
| H2B | −0.388 (2) | 0.5439 (14) | 0.0634 (9) | 0.0248* | |
| H3B | −0.355 (2) | 0.3688 (14) | −0.0209 (9) | 0.0224* | |
| H4B | −0.094 (2) | 0.2847 (13) | 0.0083 (9) | 0.0208* | |
| H5B | 0.885 (2) | 0.5353 (13) | 0.4615 (9) | 0.0195* | |
| H6B | 0.398 (2) | 0.6491 (12) | 0.3915 (9) | 0.0160* |
| Cl1A | 0.0147 (2) | 0.0165 (2) | 0.0164 (2) | 0.00768 (18) | 0.00158 (17) | 0.00171 (18) |
| Cl2A | 0.0192 (2) | 0.0251 (3) | 0.0143 (2) | 0.0077 (2) | −0.00299 (18) | −0.00561 (19) |
| O1A | 0.0188 (7) | 0.0163 (7) | 0.0172 (7) | 0.0078 (6) | 0.0020 (6) | −0.0021 (6) |
| O2A | 0.0182 (7) | 0.0184 (7) | 0.0177 (7) | 0.0084 (6) | 0.0001 (6) | −0.0036 (6) |
| C1A | 0.0174 (10) | 0.0143 (9) | 0.0181 (10) | 0.0060 (8) | 0.0036 (8) | 0.0031 (8) |
| C2A | 0.0166 (10) | 0.0196 (10) | 0.0207 (10) | 0.0089 (8) | 0.0013 (8) | 0.0042 (8) |
| C3A | 0.0202 (10) | 0.0255 (11) | 0.0166 (10) | 0.0097 (9) | −0.0037 (8) | 0.0014 (8) |
| C4A | 0.0196 (10) | 0.0208 (10) | 0.0138 (9) | 0.0067 (8) | −0.0007 (8) | −0.0015 (8) |
| N5A | 0.0154 (8) | 0.0161 (8) | 0.0138 (8) | 0.0061 (7) | 0.0005 (6) | 0.0000 (6) |
| C6A | 0.0131 (9) | 0.0135 (9) | 0.0146 (9) | 0.0039 (7) | 0.0020 (7) | 0.0031 (7) |
| C7A | 0.0137 (9) | 0.0125 (9) | 0.0154 (9) | 0.0042 (7) | 0.0033 (7) | 0.0026 (7) |
| C8A | 0.0122 (9) | 0.0187 (10) | 0.0144 (9) | 0.0048 (8) | −0.0011 (7) | 0.0024 (8) |
| C9A | 0.0150 (9) | 0.0151 (9) | 0.0121 (9) | 0.0016 (8) | 0.0004 (7) | −0.0015 (7) |
| C10A | 0.0134 (9) | 0.0133 (9) | 0.0162 (9) | 0.0039 (7) | 0.0012 (7) | −0.0005 (7) |
| N11A | 0.0126 (8) | 0.0131 (8) | 0.0122 (8) | 0.0038 (6) | −0.0005 (6) | −0.0011 (6) |
| C12A | 0.0120 (9) | 0.0138 (9) | 0.0156 (9) | 0.0025 (7) | 0.0027 (7) | 0.0024 (7) |
| C13A | 0.0140 (9) | 0.0137 (9) | 0.0150 (9) | 0.0043 (7) | 0.0021 (7) | 0.0030 (7) |
| C14A | 0.0145 (9) | 0.0116 (9) | 0.0147 (9) | 0.0046 (7) | 0.0028 (7) | 0.0010 (7) |
| C15A | 0.0124 (9) | 0.0121 (9) | 0.0138 (9) | 0.0028 (7) | 0.0027 (7) | 0.0024 (7) |
| C16A | 0.0125 (9) | 0.0145 (9) | 0.0147 (9) | 0.0033 (7) | 0.0013 (7) | 0.0027 (7) |
| C17A | 0.0133 (9) | 0.0130 (9) | 0.0148 (9) | 0.0034 (7) | 0.0014 (7) | 0.0028 (7) |
| Cl1B | 0.0148 (2) | 0.0186 (2) | 0.0217 (2) | 0.00967 (18) | 0.00275 (18) | 0.00399 (19) |
| Cl2B | 0.0183 (2) | 0.0231 (3) | 0.0153 (2) | 0.00847 (19) | −0.00197 (18) | −0.00346 (19) |
| O1B | 0.0201 (7) | 0.0182 (7) | 0.0213 (7) | 0.0103 (6) | 0.0049 (6) | 0.0004 (6) |
| O2B | 0.0170 (7) | 0.0174 (7) | 0.0167 (7) | 0.0085 (6) | −0.0007 (5) | −0.0024 (6) |
| C1B | 0.0173 (9) | 0.0151 (9) | 0.0173 (9) | 0.0070 (8) | 0.0013 (8) | 0.0010 (8) |
| C2B | 0.0168 (10) | 0.0214 (10) | 0.0210 (10) | 0.0097 (8) | −0.0012 (8) | 0.0028 (8) |
| C3B | 0.0179 (10) | 0.0207 (10) | 0.0162 (10) | 0.0052 (8) | −0.0038 (8) | −0.0006 (8) |
| C4B | 0.0207 (10) | 0.0163 (9) | 0.0157 (9) | 0.0068 (8) | 0.0010 (8) | −0.0003 (8) |
| N5B | 0.0162 (8) | 0.0149 (8) | 0.0153 (8) | 0.0059 (7) | 0.0022 (6) | 0.0011 (7) |
| C6B | 0.0120 (9) | 0.0157 (9) | 0.0165 (9) | 0.0035 (7) | 0.0031 (7) | 0.0038 (8) |
| C7B | 0.0126 (9) | 0.0141 (9) | 0.0197 (10) | 0.0065 (7) | 0.0045 (7) | 0.0048 (8) |
| C8B | 0.0148 (9) | 0.0190 (10) | 0.0156 (9) | 0.0057 (8) | −0.0010 (8) | 0.0039 (8) |
| C9B | 0.0160 (9) | 0.0143 (9) | 0.0128 (9) | 0.0024 (7) | 0.0013 (7) | −0.0001 (7) |
| C10B | 0.0123 (9) | 0.0158 (9) | 0.0157 (9) | 0.0055 (7) | 0.0022 (7) | 0.0009 (8) |
| N11B | 0.0117 (7) | 0.0142 (8) | 0.0128 (8) | 0.0048 (6) | 0.0002 (6) | −0.0001 (6) |
| C12B | 0.0120 (9) | 0.0141 (9) | 0.0155 (9) | 0.0039 (7) | 0.0022 (7) | 0.0027 (7) |
| C13B | 0.0145 (9) | 0.0117 (9) | 0.0158 (9) | 0.0035 (7) | 0.0030 (7) | 0.0034 (7) |
| C14B | 0.0141 (9) | 0.0126 (9) | 0.0166 (9) | 0.0053 (7) | 0.0049 (7) | 0.0022 (7) |
| C15B | 0.0124 (9) | 0.0137 (9) | 0.0162 (9) | 0.0045 (7) | 0.0034 (7) | 0.0030 (7) |
| C16B | 0.0106 (8) | 0.0144 (9) | 0.0152 (9) | 0.0034 (7) | 0.0009 (7) | 0.0029 (7) |
| C17B | 0.0145 (9) | 0.0137 (9) | 0.0144 (9) | 0.0045 (7) | 0.0024 (7) | 0.0034 (7) |
| Cl1A—C7A | 1.7272 (19) | C1A—C2A | 1.379 (3) |
| Cl2A—C9A | 1.7358 (19) | C1A—H1A | 0.937 (15) |
| Cl1B—C7B | 1.7276 (19) | C2A—C3A | 1.399 (3) |
| Cl2B—C9B | 1.734 (2) | C2A—H2A | 0.929 (16) |
| O1A—C6A | 1.213 (2) | C3A—C4A | 1.379 (3) |
| O2A—C12A | 1.221 (2) | C3A—H3A | 0.937 (16) |
| O1B—C6B | 1.211 (2) | C4A—C13A | 1.399 (3) |
| O2B—C12B | 1.221 (2) | C4A—H4A | 0.937 (15) |
| N5A—C13A | 1.405 (2) | C14A—C6A | 1.518 (3) |
| N5A—C14A | 1.275 (2) | C15B—C7B | 1.387 (3) |
| N11A—C16A | 1.419 (2) | C15B—C16B | 1.405 (3) |
| N11A—C12A | 1.396 (2) | C15B—C6B | 1.480 (3) |
| N11A—C14A | 1.395 (2) | C7B—C8B | 1.387 (3) |
| N5B—C13B | 1.401 (2) | C8B—C9B | 1.389 (3) |
| N5B—C14B | 1.277 (3) | C8B—H5B | 0.931 (15) |
| N11B—C16B | 1.421 (2) | C9B—C10B | 1.390 (3) |
| N11B—C12B | 1.394 (2) | C10B—C16B | 1.384 (3) |
| N11B—C14B | 1.396 (2) | C10B—H6B | 0.930 (15) |
| C15A—C7A | 1.386 (3) | C12B—C17B | 1.467 (3) |
| C15A—C16A | 1.401 (3) | C17B—C1B | 1.399 (3) |
| C15A—C6A | 1.477 (3) | C17B—C13B | 1.410 (3) |
| C7A—C8A | 1.389 (3) | C1B—C2B | 1.378 (3) |
| C8A—C9A | 1.389 (3) | C1B—H1B | 0.942 (15) |
| C8A—H5A | 0.925 (15) | C2B—C3B | 1.402 (3) |
| C9A—C10A | 1.390 (3) | C2B—H2B | 0.947 (16) |
| C10A—C16A | 1.380 (3) | C3B—C4B | 1.377 (3) |
| C10A—H6A | 0.938 (15) | C3B—H3B | 0.937 (16) |
| C12A—C17A | 1.465 (3) | C4B—C13B | 1.399 (3) |
| C17A—C1A | 1.397 (3) | C4B—H4B | 0.936 (16) |
| C17A—C13A | 1.412 (3) | C14B—C6B | 1.517 (3) |
| Cl1A—C7A—C15A | 121.65 (15) | Cl1B—C7B—C15B | 121.43 (15) |
| Cl1A—C7A—C8A | 118.05 (15) | Cl1B—C7B—C8B | 118.59 (15) |
| C15A—C7A—C8A | 120.30 (18) | C15B—C7B—C8B | 119.98 (18) |
| C7A—C15A—C6A | 132.59 (18) | C7B—C15B—C6B | 132.47 (18) |
| C7A—C15A—C16A | 118.79 (17) | C7B—C15B—C16B | 118.96 (18) |
| C6A—C15A—C16A | 108.62 (16) | C6B—C15B—C16B | 108.54 (16) |
| C15A—C6A—O1A | 129.87 (18) | C15B—C6B—O1B | 130.04 (18) |
| C15A—C6A—C14A | 104.37 (15) | C15B—C6B—C14B | 104.47 (16) |
| O1A—C6A—C14A | 125.75 (17) | O1B—C6B—C14B | 125.46 (18) |
| C6A—C14A—N5A | 126.26 (17) | C6B—C14B—N11B | 107.35 (16) |
| C6A—C14A—N11A | 107.38 (16) | C6B—C14B—N5B | 126.40 (17) |
| N5A—C14A—N11A | 126.35 (17) | N11B—C14B—N5B | 126.25 (17) |
| C14A—N5A—C13A | 115.81 (17) | C14B—N11B—C16B | 110.20 (15) |
| N5A—C13A—C4A | 118.48 (17) | C14B—N11B—C12B | 122.59 (16) |
| N5A—C13A—C17A | 122.13 (17) | C16B—N11B—C12B | 127.14 (16) |
| C4A—C13A—C17A | 119.38 (18) | N11B—C16B—C15B | 109.35 (16) |
| C13A—C4A—C3A | 119.69 (19) | N11B—C16B—C10B | 127.71 (17) |
| C13A—C4A—H4A | 120.2 (10) | C15B—C16B—C10B | 122.94 (18) |
| C3A—C4A—H4A | 120.2 (10) | C16B—C10B—C9B | 115.54 (18) |
| C4A—C3A—C2A | 120.96 (19) | C16B—C10B—H6B | 122.2 (10) |
| C4A—C3A—H3A | 119.0 (10) | C9B—C10B—H6B | 122.3 (10) |
| C2A—C3A—H3A | 120.0 (10) | C10B—C9B—C8B | 123.79 (18) |
| C3A—C2A—C1A | 120.04 (19) | C10B—C9B—Cl2B | 119.12 (15) |
| C3A—C2A—H2A | 121.2 (10) | C8B—C9B—Cl2B | 117.08 (15) |
| C1A—C2A—H2A | 118.8 (10) | C9B—C8B—C7B | 118.75 (18) |
| C2A—C1A—C17A | 119.86 (19) | C9B—C8B—H5B | 120.6 (10) |
| C2A—C1A—H1A | 119.9 (10) | C7B—C8B—H5B | 120.6 (10) |
| C17A—C1A—H1A | 120.2 (10) | N11B—C12B—O2B | 121.91 (17) |
| C13A—C17A—C1A | 120.07 (18) | N11B—C12B—C17B | 112.41 (16) |
| C13A—C17A—C12A | 120.66 (17) | O2B—C12B—C17B | 125.68 (17) |
| C1A—C17A—C12A | 119.26 (17) | C12B—C17B—C13B | 120.36 (17) |
| C17A—C12A—N11A | 112.36 (16) | C12B—C17B—C1B | 119.93 (17) |
| C17A—C12A—O2A | 125.53 (18) | C13B—C17B—C1B | 119.70 (18) |
| N11A—C12A—O2A | 122.11 (17) | C17B—C13B—N5B | 122.53 (17) |
| C12A—N11A—C14A | 122.65 (16) | C17B—C13B—C4B | 119.38 (18) |
| C12A—N11A—C16A | 127.27 (16) | N5B—C13B—C4B | 118.09 (17) |
| C14A—N11A—C16A | 110.08 (15) | C13B—N5B—C14B | 115.64 (16) |
| N11A—C16A—C15A | 109.50 (16) | C13B—C4B—C3B | 120.22 (19) |
| N11A—C16A—C10A | 127.57 (18) | C13B—C4B—H4B | 119.5 (10) |
| C15A—C16A—C10A | 122.93 (18) | C3B—C4B—H4B | 120.2 (10) |
| C16A—C10A—C9A | 115.95 (18) | C4B—C3B—C2B | 120.39 (19) |
| C16A—C10A—H6A | 122.5 (10) | C4B—C3B—H3B | 118.8 (10) |
| C9A—C10A—H6A | 121.5 (10) | C2B—C3B—H3B | 120.8 (10) |
| C10A—C9A—C8A | 123.45 (18) | C3B—C2B—C1B | 120.12 (19) |
| C10A—C9A—Cl2A | 118.47 (15) | C3B—C2B—H2B | 120.2 (10) |
| C8A—C9A—Cl2A | 118.07 (15) | C1B—C2B—H2B | 119.6 (10) |
| C9A—C8A—C7A | 118.51 (17) | C17B—C1B—C2B | 120.18 (18) |
| C9A—C8A—H5A | 120.8 (10) | C17B—C1B—H1B | 120.2 (10) |
| C7A—C8A—H5A | 120.6 (10) | C2B—C1B—H1B | 119.6 (10) |
| H··· | ||||
| C1B—H1B···Cl1Ai | 0.94 (2) | 2.73 (2) | 3.637 (2) | 162 (1) |
| C2A—H2A···O1Bii | 0.93 (2) | 2.54 (2) | 3.264 (3) | 135 (1) |
| C4B—H4B···N5Aiii | 0.94 (2) | 2.56 (2) | 3.422 (3) | 154 (1) |
| C10A—H6A···Cl2Biv | 0.94 (2) | 2.67 (2) | 3.585 (2) | 165 (1) |
Hydrogen-bond geometry (Å, °)
| H⋯ | ||||
|---|---|---|---|---|
| C1 | 0.94 (2) | 2.73 (2) | 3.637 (2) | 162 (1) |
| C2 | 0.93 (2) | 2.54 (2) | 3.264 (3) | 135 (1) |
| C4 | 0.94 (2) | 2.56 (2) | 3.422 (3) | 154 (1) |
| C10 | 0.94 (2) | 2.67 (2) | 3.585 (2) | 165 (1) |
Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .