| Literature DB >> 21577604 |
Jerry P Jasinski, Ray J Butcher, Q N M Hakim Al-Arique, H S Yathirajan, B Narayana.
Abstract
In the cation of the title salt, C(Entities:
Year: 2009 PMID: 21577604 PMCID: PMC2970075 DOI: 10.1107/S1600536809032693
Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN: 1600-5368
| C11H12ClN2O+·C6H2N3O7− | |
| Monoclinic, | Cu |
| Hall symbol: -P 2yn | Cell parameters from 4324 reflections |
| θ = 4.1–74.1° | |
| µ = 2.40 mm−1 | |
| β = 97.642 (9)° | Chunk, pale yellow |
| 0.44 × 0.37 × 0.23 mm | |
| Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector | 3616 independent reflections |
| Radiation source: Enhance (Cu) X-ray Source | 3198 reflections with |
| graphite | |
| Detector resolution: 10.5081 pixels mm-1 | θmax = 74.0°, θmin = 4.1° |
| ω scans | |
| Absorption correction: multi-scan ( | |
| 6948 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 | |
| 3616 reflections | (Δ/σ)max < 0.001 |
| 281 parameters | Δρmax = 0.30 e Å−3 |
| 0 restraints | Δρmin = −0.29 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 |
| Cl1A | 0.86173 (5) | 0.88220 (3) | 0.687448 (19) | 0.02115 (12) | |
| O1A | 0.51748 (16) | 0.63234 (9) | 0.76768 (5) | 0.0210 (2) | |
| N1A | 0.37082 (17) | 0.50513 (9) | 0.69885 (6) | 0.0150 (3) | |
| C1A | 0.5193 (2) | 0.58121 (11) | 0.71692 (8) | 0.0162 (3) | |
| C2A | 0.6526 (2) | 0.58732 (11) | 0.66975 (7) | 0.0153 (3) | |
| C3A | 0.6432 (2) | 0.52080 (11) | 0.61613 (7) | 0.0154 (3) | |
| N4A | 0.50951 (17) | 0.44532 (10) | 0.60742 (6) | 0.0162 (3) | |
| H4AA | 0.5124 | 0.4000 | 0.5744 | 0.019* | |
| C5A | 0.3734 (2) | 0.43685 (11) | 0.64690 (7) | 0.0157 (3) | |
| C6A | 0.2346 (2) | 0.35986 (12) | 0.63478 (8) | 0.0196 (3) | |
| H6AA | 0.2378 | 0.3105 | 0.5994 | 0.024* | |
| C7A | 0.0949 (2) | 0.35698 (13) | 0.67466 (9) | 0.0226 (3) | |
| H7AA | 0.0018 | 0.3046 | 0.6677 | 0.027* | |
| C8A | 0.0903 (2) | 0.43233 (13) | 0.72609 (8) | 0.0227 (3) | |
| H8AA | −0.0095 | 0.4328 | 0.7524 | 0.027* | |
| C9A | 0.2275 (2) | 0.50377 (12) | 0.73803 (8) | 0.0190 (3) | |
| H9AA | 0.2254 | 0.5532 | 0.7734 | 0.023* | |
| C10A | 0.7963 (2) | 0.67205 (12) | 0.68363 (8) | 0.0171 (3) | |
| H10A | 0.9037 | 0.6568 | 0.6595 | 0.021* | |
| H10B | 0.8409 | 0.6754 | 0.7327 | 0.021* | |
| C11A | 0.7098 (2) | 0.77552 (12) | 0.65971 (8) | 0.0187 (3) | |
| H11A | 0.5904 | 0.7844 | 0.6778 | 0.022* | |
| H11B | 0.6843 | 0.7757 | 0.6097 | 0.022* | |
| C12A | 0.7717 (2) | 0.52487 (13) | 0.56313 (8) | 0.0202 (3) | |
| H12A | 0.9003 | 0.5188 | 0.5848 | 0.030* | |
| H12B | 0.7554 | 0.5914 | 0.5388 | 0.030* | |
| H12C | 0.7433 | 0.4671 | 0.5312 | 0.030* | |
| O1B | 0.57412 (15) | 0.30604 (8) | 0.51298 (5) | 0.0185 (2) | |
| O21B | 0.81068 (17) | 0.36265 (9) | 0.42333 (6) | 0.0246 (3) | |
| O22B | 0.75216 (16) | 0.25511 (9) | 0.33919 (6) | 0.0223 (3) | |
| O41B | 0.88575 (16) | −0.10609 (9) | 0.40701 (6) | 0.0233 (3) | |
| O42B | 0.78903 (17) | −0.16264 (9) | 0.49860 (6) | 0.0248 (3) | |
| O61B | 0.52961 (16) | 0.07476 (10) | 0.64703 (6) | 0.0250 (3) | |
| O62B | 0.61759 (18) | 0.23621 (9) | 0.64474 (6) | 0.0257 (3) | |
| N2B | 0.76693 (17) | 0.27587 (10) | 0.40009 (7) | 0.0174 (3) | |
| N4B | 0.81817 (17) | −0.09140 (10) | 0.45962 (7) | 0.0175 (3) | |
| N6B | 0.59534 (18) | 0.14919 (11) | 0.61918 (6) | 0.0180 (3) | |
| C1B | 0.6503 (2) | 0.21995 (11) | 0.50651 (7) | 0.0145 (3) | |
| C2B | 0.7355 (2) | 0.19261 (12) | 0.44702 (7) | 0.0153 (3) | |
| C3B | 0.7866 (2) | 0.09381 (12) | 0.43082 (7) | 0.0158 (3) | |
| H3BA | 0.8335 | 0.0804 | 0.3894 | 0.019* | |
| C4B | 0.76828 (19) | 0.01382 (12) | 0.47634 (7) | 0.0156 (3) | |
| C5B | 0.70412 (19) | 0.03312 (12) | 0.53788 (7) | 0.0157 (3) | |
| H5BA | 0.6955 | −0.0220 | 0.5691 | 0.019* | |
| C6B | 0.6534 (2) | 0.13254 (12) | 0.55290 (7) | 0.0151 (3) |
| Cl1A | 0.0225 (2) | 0.0160 (2) | 0.0248 (2) | −0.00529 (13) | 0.00290 (15) | −0.00297 (14) |
| O1A | 0.0287 (6) | 0.0192 (6) | 0.0158 (5) | −0.0004 (4) | 0.0054 (4) | −0.0034 (4) |
| N1A | 0.0175 (6) | 0.0129 (6) | 0.0149 (6) | 0.0017 (5) | 0.0037 (5) | 0.0018 (5) |
| C1A | 0.0202 (7) | 0.0121 (7) | 0.0157 (7) | 0.0020 (6) | 0.0006 (6) | 0.0025 (6) |
| C2A | 0.0158 (7) | 0.0143 (7) | 0.0154 (7) | 0.0002 (6) | 0.0009 (5) | 0.0019 (5) |
| C3A | 0.0154 (7) | 0.0140 (7) | 0.0167 (7) | 0.0020 (5) | 0.0018 (5) | 0.0017 (6) |
| N4A | 0.0189 (6) | 0.0144 (6) | 0.0159 (6) | 0.0004 (5) | 0.0044 (5) | −0.0028 (5) |
| C5A | 0.0187 (7) | 0.0128 (7) | 0.0156 (7) | 0.0032 (6) | 0.0023 (6) | 0.0027 (5) |
| C6A | 0.0218 (8) | 0.0136 (7) | 0.0232 (8) | 0.0012 (6) | 0.0023 (6) | 0.0006 (6) |
| C7A | 0.0205 (8) | 0.0169 (7) | 0.0303 (9) | −0.0027 (6) | 0.0035 (7) | 0.0057 (6) |
| C8A | 0.0225 (8) | 0.0234 (8) | 0.0237 (8) | 0.0017 (6) | 0.0089 (6) | 0.0076 (7) |
| C9A | 0.0226 (7) | 0.0190 (7) | 0.0165 (7) | 0.0039 (6) | 0.0069 (6) | 0.0048 (6) |
| C10A | 0.0176 (7) | 0.0171 (7) | 0.0163 (7) | −0.0007 (6) | 0.0010 (6) | −0.0011 (6) |
| C11A | 0.0180 (7) | 0.0150 (7) | 0.0221 (8) | −0.0044 (6) | −0.0002 (6) | −0.0017 (6) |
| C12A | 0.0213 (7) | 0.0221 (8) | 0.0183 (7) | −0.0019 (6) | 0.0063 (6) | −0.0027 (6) |
| O1B | 0.0219 (5) | 0.0163 (5) | 0.0175 (5) | 0.0027 (4) | 0.0037 (4) | −0.0018 (4) |
| O21B | 0.0309 (6) | 0.0177 (6) | 0.0261 (6) | −0.0055 (5) | 0.0071 (5) | −0.0003 (5) |
| O22B | 0.0257 (6) | 0.0268 (6) | 0.0149 (5) | 0.0026 (5) | 0.0045 (4) | 0.0025 (5) |
| O41B | 0.0264 (6) | 0.0222 (6) | 0.0226 (6) | 0.0026 (5) | 0.0085 (5) | −0.0070 (5) |
| O42B | 0.0296 (6) | 0.0152 (5) | 0.0313 (7) | 0.0001 (5) | 0.0103 (5) | 0.0018 (5) |
| O61B | 0.0266 (6) | 0.0304 (7) | 0.0199 (6) | −0.0034 (5) | 0.0096 (5) | 0.0024 (5) |
| O62B | 0.0412 (7) | 0.0208 (6) | 0.0149 (5) | 0.0088 (5) | 0.0029 (5) | −0.0030 (4) |
| N2B | 0.0148 (6) | 0.0188 (7) | 0.0190 (6) | 0.0009 (5) | 0.0039 (5) | 0.0017 (5) |
| N4B | 0.0141 (6) | 0.0172 (6) | 0.0210 (7) | −0.0015 (5) | 0.0018 (5) | −0.0039 (5) |
| N6B | 0.0177 (6) | 0.0220 (7) | 0.0143 (6) | 0.0041 (5) | 0.0027 (5) | 0.0012 (5) |
| C1B | 0.0129 (6) | 0.0157 (7) | 0.0148 (7) | −0.0008 (5) | 0.0010 (5) | −0.0021 (6) |
| C2B | 0.0141 (6) | 0.0178 (7) | 0.0140 (7) | −0.0020 (5) | 0.0016 (5) | 0.0011 (6) |
| C3B | 0.0131 (7) | 0.0198 (7) | 0.0145 (7) | −0.0007 (6) | 0.0025 (5) | −0.0026 (6) |
| C4B | 0.0138 (7) | 0.0155 (7) | 0.0175 (7) | −0.0005 (5) | 0.0019 (5) | −0.0036 (6) |
| C5B | 0.0125 (7) | 0.0166 (7) | 0.0178 (7) | −0.0014 (5) | 0.0011 (5) | 0.0007 (6) |
| C6B | 0.0136 (7) | 0.0186 (7) | 0.0133 (7) | −0.0003 (5) | 0.0028 (5) | −0.0011 (6) |
| Cl1A—C11A | 1.7979 (15) | C11A—H11A | 0.9900 |
| O1A—C1A | 1.2073 (19) | C11A—H11B | 0.9900 |
| N1A—C5A | 1.3582 (19) | C12A—H12A | 0.9800 |
| N1A—C9A | 1.3835 (19) | C12A—H12B | 0.9800 |
| N1A—C1A | 1.4636 (19) | C12A—H12C | 0.9800 |
| C1A—C2A | 1.440 (2) | O1B—C1B | 1.2489 (18) |
| C2A—C3A | 1.362 (2) | O21B—N2B | 1.2303 (18) |
| C2A—C10A | 1.507 (2) | O22B—N2B | 1.2337 (17) |
| C3A—N4A | 1.3659 (19) | O41B—N4B | 1.2307 (17) |
| C3A—C12A | 1.502 (2) | O42B—N4B | 1.2355 (18) |
| N4A—C5A | 1.3485 (19) | O61B—N6B | 1.2317 (18) |
| N4A—H4AA | 0.8800 | O62B—N6B | 1.2279 (18) |
| C5A—C6A | 1.409 (2) | N2B—C2B | 1.4572 (19) |
| C6A—C7A | 1.372 (2) | N4B—C4B | 1.4469 (19) |
| C6A—H6AA | 0.9500 | N6B—C6B | 1.4559 (19) |
| C7A—C8A | 1.412 (2) | C1B—C6B | 1.451 (2) |
| C7A—H7AA | 0.9500 | C1B—C2B | 1.452 (2) |
| C8A—C9A | 1.352 (2) | C2B—C3B | 1.370 (2) |
| C8A—H8AA | 0.9500 | C3B—C4B | 1.387 (2) |
| C9A—H9AA | 0.9500 | C3B—H3BA | 0.9500 |
| C10A—C11A | 1.517 (2) | C4B—C5B | 1.392 (2) |
| C10A—H10A | 0.9900 | C5B—C6B | 1.371 (2) |
| C10A—H10B | 0.9900 | C5B—H5BA | 0.9500 |
| C5A—N1A—C9A | 120.69 (13) | Cl1A—C11A—H11A | 109.5 |
| C5A—N1A—C1A | 122.17 (12) | C10A—C11A—H11B | 109.5 |
| C9A—N1A—C1A | 117.12 (13) | Cl1A—C11A—H11B | 109.5 |
| O1A—C1A—C2A | 126.96 (14) | H11A—C11A—H11B | 108.1 |
| O1A—C1A—N1A | 118.57 (14) | C3A—C12A—H12A | 109.5 |
| C2A—C1A—N1A | 114.47 (13) | C3A—C12A—H12B | 109.5 |
| C3A—C2A—C1A | 120.70 (14) | H12A—C12A—H12B | 109.5 |
| C3A—C2A—C10A | 123.83 (14) | C3A—C12A—H12C | 109.5 |
| C1A—C2A—C10A | 115.46 (13) | H12A—C12A—H12C | 109.5 |
| C2A—C3A—N4A | 120.25 (13) | H12B—C12A—H12C | 109.5 |
| C2A—C3A—C12A | 124.01 (14) | O21B—N2B—O22B | 123.36 (13) |
| N4A—C3A—C12A | 115.73 (13) | O21B—N2B—C2B | 118.35 (13) |
| C5A—N4A—C3A | 123.23 (13) | O22B—N2B—C2B | 118.27 (13) |
| C5A—N4A—H4AA | 118.4 | O41B—N4B—O42B | 122.99 (13) |
| C3A—N4A—H4AA | 118.4 | O41B—N4B—C4B | 118.67 (13) |
| N4A—C5A—N1A | 118.62 (13) | O42B—N4B—C4B | 118.33 (13) |
| N4A—C5A—C6A | 121.39 (14) | O62B—N6B—O61B | 123.63 (13) |
| N1A—C5A—C6A | 119.99 (14) | O62B—N6B—C6B | 118.15 (13) |
| C7A—C6A—C5A | 119.23 (15) | O61B—N6B—C6B | 118.20 (13) |
| C7A—C6A—H6AA | 120.4 | O1B—C1B—C6B | 125.86 (14) |
| C5A—C6A—H6AA | 120.4 | O1B—C1B—C2B | 122.74 (13) |
| C6A—C7A—C8A | 119.56 (15) | C6B—C1B—C2B | 111.23 (13) |
| C6A—C7A—H7AA | 120.2 | C3B—C2B—C1B | 125.03 (13) |
| C8A—C7A—H7AA | 120.2 | C3B—C2B—N2B | 117.04 (13) |
| C9A—C8A—C7A | 120.20 (15) | C1B—C2B—N2B | 117.92 (13) |
| C9A—C8A—H8AA | 119.9 | C2B—C3B—C4B | 118.42 (14) |
| C7A—C8A—H8AA | 119.9 | C2B—C3B—H3BA | 120.8 |
| C8A—C9A—N1A | 120.20 (15) | C4B—C3B—H3BA | 120.8 |
| C8A—C9A—H9AA | 119.9 | C3B—C4B—C5B | 121.21 (14) |
| N1A—C9A—H9AA | 119.9 | C3B—C4B—N4B | 119.28 (13) |
| C2A—C10A—C11A | 108.90 (12) | C5B—C4B—N4B | 119.51 (13) |
| C2A—C10A—H10A | 109.9 | C6B—C5B—C4B | 119.29 (14) |
| C11A—C10A—H10A | 109.9 | C6B—C5B—H5BA | 120.4 |
| C2A—C10A—H10B | 109.9 | C4B—C5B—H5BA | 120.4 |
| C11A—C10A—H10B | 109.9 | C5B—C6B—C1B | 124.09 (14) |
| H10A—C10A—H10B | 108.3 | C5B—C6B—N6B | 116.97 (13) |
| C10A—C11A—Cl1A | 110.85 (11) | C1B—C6B—N6B | 118.92 (13) |
| C10A—C11A—H11A | 109.5 | ||
| C5A—N1A—C1A—O1A | −172.72 (13) | C2A—C10A—C11A—Cl1A | 170.43 (10) |
| C9A—N1A—C1A—O1A | 6.0 (2) | O1B—C1B—C2B—C3B | −165.97 (15) |
| C5A—N1A—C1A—C2A | 8.26 (19) | C6B—C1B—C2B—C3B | 9.5 (2) |
| C9A—N1A—C1A—C2A | −173.04 (12) | O1B—C1B—C2B—N2B | 13.0 (2) |
| O1A—C1A—C2A—C3A | 176.59 (15) | C6B—C1B—C2B—N2B | −171.52 (12) |
| N1A—C1A—C2A—C3A | −4.5 (2) | O21B—N2B—C2B—C3B | −145.18 (14) |
| O1A—C1A—C2A—C10A | −4.5 (2) | O22B—N2B—C2B—C3B | 33.30 (19) |
| N1A—C1A—C2A—C10A | 174.42 (12) | O21B—N2B—C2B—C1B | 35.76 (19) |
| C1A—C2A—C3A—N4A | −1.8 (2) | O22B—N2B—C2B—C1B | −145.77 (14) |
| C10A—C2A—C3A—N4A | 179.40 (13) | C1B—C2B—C3B—C4B | −4.6 (2) |
| C1A—C2A—C3A—C12A | 177.36 (14) | N2B—C2B—C3B—C4B | 176.39 (13) |
| C10A—C2A—C3A—C12A | −1.5 (2) | C2B—C3B—C4B—C5B | −1.6 (2) |
| C2A—C3A—N4A—C5A | 5.2 (2) | C2B—C3B—C4B—N4B | 178.83 (13) |
| C12A—C3A—N4A—C5A | −174.00 (13) | O41B—N4B—C4B—C3B | 4.1 (2) |
| C3A—N4A—C5A—N1A | −1.5 (2) | O42B—N4B—C4B—C3B | −175.13 (13) |
| C3A—N4A—C5A—C6A | 177.89 (14) | O41B—N4B—C4B—C5B | −175.43 (13) |
| C9A—N1A—C5A—N4A | 175.85 (13) | O42B—N4B—C4B—C5B | 5.3 (2) |
| C1A—N1A—C5A—N4A | −5.5 (2) | C3B—C4B—C5B—C6B | 1.8 (2) |
| C9A—N1A—C5A—C6A | −3.5 (2) | N4B—C4B—C5B—C6B | −178.67 (13) |
| C1A—N1A—C5A—C6A | 175.12 (13) | C4B—C5B—C6B—C1B | 4.3 (2) |
| N4A—C5A—C6A—C7A | −177.42 (14) | C4B—C5B—C6B—N6B | −177.30 (13) |
| N1A—C5A—C6A—C7A | 2.0 (2) | O1B—C1B—C6B—C5B | 166.06 (15) |
| C5A—C6A—C7A—C8A | 1.3 (2) | C2B—C1B—C6B—C5B | −9.2 (2) |
| C6A—C7A—C8A—C9A | −3.1 (2) | O1B—C1B—C6B—N6B | −12.4 (2) |
| C7A—C8A—C9A—N1A | 1.6 (2) | C2B—C1B—C6B—N6B | 172.34 (12) |
| C5A—N1A—C9A—C8A | 1.8 (2) | O62B—N6B—C6B—C5B | 152.45 (14) |
| C1A—N1A—C9A—C8A | −176.96 (13) | O61B—N6B—C6B—C5B | −26.3 (2) |
| C3A—C2A—C10A—C11A | 100.58 (17) | O62B—N6B—C6B—C1B | −29.02 (19) |
| C1A—C2A—C10A—C11A | −78.29 (16) | O61B—N6B—C6B—C1B | 152.23 (13) |
| H··· | ||||
| N4A—H4AA···O1B | 0.88 | 1.82 | 2.6811 (16) | 167 |
| N4A—H4AA···O62B | 0.88 | 2.58 | 2.8632 (17) | 100 |
| C5B—H5BA···Cl1Ai | 0.95 | 2.79 | 3.6112 (16) | 146 |
| C7A—H7AA···O1Aii | 0.95 | 2.57 | 3.2446 (19) | 128 |
| C12A—H12C···O1B | 0.98 | 2.41 | 3.2477 (19) | 144 |
| C9A—H9AA···O61Biii | 0.95 | 2.61 | 3.2734 (19) | 127 |
| C12A—H12A···O21Biv | 0.98 | 2.62 | 3.340 (2) | 131 |
| C10A—H10B···O62Bv | 0.99 | 2.54 | 3.494 (2) | 161 |
| C11A—H11A···O22Bvi | 0.99 | 2.52 | 3.385 (2) | 146 |
| C11A—H11B···O42Bvii | 0.99 | 2.56 | 3.431 (2) | 147 |
Hydrogen-bond geometry (Å, °)
| H⋯ | ||||
|---|---|---|---|---|
| N4 | 0.88 | 1.82 | 2.6811 (16) | 167 |
| N4 | 0.88 | 2.58 | 2.8632 (17) | 100 |
| C5 | 0.95 | 2.79 | 3.6112 (16) | 146 |
| C7 | 0.95 | 2.57 | 3.2446 (19) | 128 |
| C12 | 0.98 | 2.41 | 3.2477 (19) | 144 |
| C9 | 0.95 | 2.61 | 3.2734 (19) | 127 |
| C12 | 0.98 | 2.62 | 3.340 (2) | 131 |
| C10 | 0.99 | 2.54 | 3.494 (2) | 161 |
| C11 | 0.99 | 2.52 | 3.385 (2) | 146 |
| C11 | 0.99 | 2.56 | 3.431 (2) | 147 |
Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .