| Literature DB >> 21836982 |
Shahzad Sharif, Islam Ullah Khan, Tariq Mahmood, Sung Kwon Kang.
Abstract
In the title compound, C(15)H(14)N(2)O(5)S, two similar mol-ecules comprise the asymmetric unit, which are linked by strong inter-molecular C-H⋯π inter-actions. Both mol-ecules are bent, with dihedral angles of 71.94 (16) and 74.62 (15)° between the benzene rings. An intra-molecular N-H⋯O hydrogen bond occurs in each mol-ecule. In the crystal, inter-molecular N-H⋯O and O-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network.Entities:
Year: 2011 PMID: 21836982 PMCID: PMC3151891 DOI: 10.1107/S1600536811020307
Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN: 1600-5368
| C15H14N2O5S | |
| Monoclinic, | Mo |
| Hall symbol: P 2yb | Cell parameters from 1295 reflections |
| θ = 2.8–18.7° | |
| µ = 0.24 mm−1 | |
| β = 109.47 (3)° | Block, violet |
| 0.25 × 0.12 × 0.09 mm | |
| Bruker APEXII CCD diffractometer | 2926 independent reflections |
| graphite | 1470 reflections with |
| φ and ω scans | θmax = 25.5°, θmin = 2.8° |
| Absorption correction: multi-scan ( | |
| 2926 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 | |
| 2926 reflections | (Δ/σ)max < 0.001 |
| 415 parameters | Δρmax = 0.26 e Å−3 |
| 1 restraint | Δρmin = −0.24 e Å−3 |
| Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. |
| Refinement. Refinement of |
| C1 | 0.9116 (7) | 0.1951 (5) | 0.4462 (5) | 0.0489 (17) | |
| C2 | 0.8856 (6) | 0.1876 (4) | 0.3361 (5) | 0.0378 (15) | |
| C3 | 0.9664 (8) | 0.2491 (5) | 0.2895 (6) | 0.069 (2) | |
| H3 | 0.9489 | 0.2433 | 0.2157 | 0.082* | |
| C4 | 1.0705 (8) | 0.3179 (6) | 0.3474 (7) | 0.068 (2) | |
| H4 | 1.124 | 0.3585 | 0.3143 | 0.081* | |
| C5 | 1.0948 (8) | 0.3260 (6) | 0.4565 (7) | 0.078 (2) | |
| H5 | 1.1645 | 0.3736 | 0.4972 | 0.094* | |
| C6 | 1.0181 (8) | 0.2652 (6) | 0.5064 (6) | 0.0547 (18) | |
| H6 | 1.0374 | 0.271 | 0.5804 | 0.066* | |
| C7 | 0.8274 (7) | 0.1297 (5) | 0.4990 (5) | 0.0444 (16) | |
| O8 | 0.7297 (6) | 0.0692 (4) | 0.4533 (4) | 0.0761 (16) | |
| O9 | 0.8716 (5) | 0.1415 (4) | 0.6050 (4) | 0.0753 (14) | |
| H9 | 0.8211 | 0.1043 | 0.63 | 0.113* | |
| N10 | 0.7746 (6) | 0.1191 (4) | 0.2728 (4) | 0.0556 (15) | |
| H10 | 0.7657 | 0.0613 | 0.3017 | 0.067* | |
| S11 | 0.6629 (2) | 0.13965 (13) | 0.15141 (13) | 0.0496 (5) | |
| O12 | 0.5537 (5) | 0.0600 (3) | 0.1345 (3) | 0.0650 (13) | |
| O13 | 0.7415 (4) | 0.1479 (3) | 0.0766 (3) | 0.0601 (12) | |
| C14 | 0.5771 (6) | 0.2586 (5) | 0.1545 (5) | 0.0409 (16) | |
| C15 | 0.5660 (7) | 0.3302 (5) | 0.0747 (5) | 0.0505 (18) | |
| H15 | 0.6111 | 0.3183 | 0.0225 | 0.061* | |
| C16 | 0.4882 (7) | 0.4181 (5) | 0.0734 (5) | 0.0523 (19) | |
| H16 | 0.48 | 0.4663 | 0.0196 | 0.063* | |
| C17 | 0.4204 (6) | 0.4379 (5) | 0.1504 (5) | 0.0374 (15) | |
| C18 | 0.4315 (7) | 0.3678 (5) | 0.2282 (5) | 0.0485 (18) | |
| H18 | 0.3873 | 0.3809 | 0.2806 | 0.058* | |
| C19 | 0.5082 (7) | 0.2768 (5) | 0.2307 (5) | 0.0479 (17) | |
| H19 | 0.5134 | 0.228 | 0.2834 | 0.057* | |
| N20 | 0.3395 (5) | 0.5312 (4) | 0.1386 (4) | 0.0434 (13) | |
| H20 | 0.3362 | 0.5668 | 0.0827 | 0.052* | |
| C21 | 0.2673 (6) | 0.5729 (5) | 0.2010 (5) | 0.0411 (16) | |
| O22 | 0.2672 (5) | 0.5316 (3) | 0.2864 (3) | 0.0580 (13) | |
| C23 | 0.1884 (7) | 0.6728 (4) | 0.1635 (5) | 0.059 (2) | |
| H23A | 0.2015 | 0.6925 | 0.0967 | 0.088* | |
| H23B | 0.2307 | 0.7246 | 0.217 | 0.088* | |
| H23C | 0.0825 | 0.6653 | 0.1527 | 0.088* | |
| C24 | −0.0124 (7) | 0.9059 (5) | 0.1004 (5) | 0.0449 (16) | |
| C25 | 0.0910 (7) | 0.9800 (5) | 0.1592 (5) | 0.0437 (17) | |
| C26 | 0.1722 (7) | 1.0380 (5) | 0.1075 (6) | 0.061 (2) | |
| H26 | 0.2361 | 1.09 | 0.1449 | 0.074* | |
| C27 | 0.1581 (7) | 1.0185 (6) | 0.0021 (6) | 0.064 (2) | |
| H27 | 0.2137 | 1.0569 | −0.0312 | 0.077* | |
| C28 | 0.0617 (8) | 0.9422 (6) | −0.0555 (6) | 0.071 (2) | |
| H28 | 0.0553 | 0.9272 | −0.1261 | 0.085* | |
| C29 | −0.0240 (7) | 0.8892 (5) | −0.0065 (6) | 0.0510 (18) | |
| H29 | −0.0924 | 0.8405 | −0.0463 | 0.061* | |
| C30 | −0.1013 (7) | 0.8458 (5) | 0.1504 (6) | 0.0479 (17) | |
| O31 | −0.1843 (5) | 0.7725 (4) | 0.0872 (4) | 0.0677 (14) | |
| H31 | −0.2313 | 0.7413 | 0.12 | 0.101* | |
| O32 | −0.1066 (5) | 0.8583 (4) | 0.2407 (4) | 0.0691 (15) | |
| N33 | 0.1094 (5) | 0.9963 (4) | 0.2685 (4) | 0.0555 (15) | |
| H33 | 0.0295 | 0.9965 | 0.2869 | 0.067* | |
| S34 | 0.2731 (2) | 1.01499 (13) | 0.36347 (14) | 0.0574 (5) | |
| O35 | 0.3439 (5) | 1.1036 (3) | 0.3377 (4) | 0.0690 (14) | |
| O36 | 0.2365 (5) | 1.0137 (4) | 0.4614 (3) | 0.0713 (13) | |
| C37 | 0.3874 (7) | 0.9084 (5) | 0.3622 (5) | 0.0471 (17) | |
| C38 | 0.4644 (7) | 0.9058 (5) | 0.2911 (6) | 0.059 (2) | |
| H38 | 0.4576 | 0.9616 | 0.2457 | 0.07* | |
| C39 | 0.5520 (7) | 0.8235 (6) | 0.2842 (6) | 0.0584 (19) | |
| H39 | 0.6053 | 0.8234 | 0.2358 | 0.07* | |
| C40 | 0.5584 (7) | 0.7408 (5) | 0.3516 (5) | 0.0498 (18) | |
| C41 | 0.4833 (7) | 0.7435 (5) | 0.4263 (5) | 0.0540 (19) | |
| H41 | 0.4912 | 0.6889 | 0.4733 | 0.065* | |
| C42 | 0.3979 (7) | 0.8271 (5) | 0.4301 (5) | 0.0530 (18) | |
| H42 | 0.3462 | 0.8289 | 0.4794 | 0.064* | |
| N43 | 0.6463 (5) | 0.6529 (4) | 0.3513 (4) | 0.0563 (15) | |
| H43 | 0.6701 | 0.6161 | 0.4089 | 0.068* | |
| C44 | 0.6993 (7) | 0.6179 (6) | 0.2710 (6) | 0.0548 (19) | |
| O45 | 0.6655 (5) | 0.6604 (4) | 0.1829 (4) | 0.0682 (14) | |
| C46 | 0.7926 (7) | 0.5216 (6) | 0.2971 (5) | 0.071 (2) | |
| H46A | 0.8045 | 0.5004 | 0.3695 | 0.106* | |
| H46B | 0.8903 | 0.5345 | 0.291 | 0.106* | |
| H46C | 0.7426 | 0.4684 | 0.2475 | 0.106* |
| C1 | 0.055 (4) | 0.049 (5) | 0.045 (4) | 0.016 (4) | 0.019 (4) | 0.011 (4) |
| C2 | 0.038 (4) | 0.027 (4) | 0.051 (4) | 0.014 (3) | 0.019 (4) | 0.012 (4) |
| C3 | 0.077 (6) | 0.060 (5) | 0.071 (6) | −0.005 (4) | 0.027 (5) | 0.003 (4) |
| C4 | 0.050 (5) | 0.063 (6) | 0.081 (6) | −0.001 (4) | 0.009 (5) | 0.017 (5) |
| C5 | 0.063 (6) | 0.059 (6) | 0.094 (7) | −0.003 (4) | 0.002 (5) | 0.006 (5) |
| C6 | 0.049 (4) | 0.051 (5) | 0.057 (5) | −0.004 (4) | 0.007 (4) | 0.004 (4) |
| C7 | 0.050 (4) | 0.048 (4) | 0.035 (4) | 0.010 (4) | 0.013 (3) | 0.004 (4) |
| O8 | 0.091 (4) | 0.081 (4) | 0.056 (3) | −0.030 (3) | 0.023 (3) | 0.005 (3) |
| O9 | 0.083 (4) | 0.088 (4) | 0.054 (3) | −0.007 (3) | 0.022 (3) | 0.003 (3) |
| N10 | 0.081 (4) | 0.034 (3) | 0.046 (3) | 0.006 (3) | 0.014 (3) | 0.008 (3) |
| S11 | 0.0681 (12) | 0.0425 (11) | 0.0387 (10) | −0.0015 (10) | 0.0186 (9) | −0.0069 (9) |
| O12 | 0.101 (4) | 0.038 (3) | 0.063 (3) | −0.023 (3) | 0.038 (3) | −0.013 (2) |
| O13 | 0.079 (3) | 0.056 (3) | 0.057 (3) | −0.001 (3) | 0.038 (3) | −0.010 (3) |
| C14 | 0.044 (4) | 0.036 (4) | 0.041 (4) | 0.002 (3) | 0.011 (3) | 0.001 (3) |
| C15 | 0.073 (5) | 0.053 (5) | 0.038 (4) | 0.003 (4) | 0.035 (4) | 0.007 (4) |
| C16 | 0.065 (5) | 0.054 (5) | 0.040 (4) | 0.011 (4) | 0.020 (4) | 0.015 (3) |
| C17 | 0.041 (4) | 0.033 (4) | 0.039 (4) | 0.001 (3) | 0.014 (3) | 0.002 (3) |
| C18 | 0.055 (4) | 0.052 (5) | 0.051 (4) | 0.010 (3) | 0.033 (4) | 0.018 (4) |
| C19 | 0.064 (4) | 0.052 (5) | 0.033 (4) | −0.004 (4) | 0.023 (4) | 0.013 (4) |
| N20 | 0.051 (3) | 0.048 (4) | 0.037 (3) | 0.004 (3) | 0.023 (3) | 0.012 (3) |
| C21 | 0.043 (4) | 0.042 (4) | 0.034 (4) | −0.011 (3) | 0.006 (3) | −0.005 (3) |
| O22 | 0.077 (3) | 0.058 (3) | 0.051 (3) | 0.004 (3) | 0.036 (3) | 0.001 (3) |
| C23 | 0.069 (5) | 0.052 (5) | 0.052 (4) | 0.014 (4) | 0.017 (4) | −0.008 (4) |
| C24 | 0.043 (4) | 0.048 (4) | 0.045 (4) | 0.004 (3) | 0.016 (3) | 0.011 (4) |
| C25 | 0.046 (4) | 0.048 (5) | 0.042 (4) | 0.013 (3) | 0.020 (4) | 0.009 (3) |
| C26 | 0.065 (5) | 0.061 (5) | 0.058 (5) | −0.001 (4) | 0.022 (4) | −0.004 (4) |
| C27 | 0.065 (5) | 0.064 (6) | 0.063 (5) | 0.008 (4) | 0.023 (4) | 0.026 (5) |
| C28 | 0.068 (5) | 0.089 (7) | 0.053 (5) | −0.002 (5) | 0.017 (4) | 0.008 (5) |
| C29 | 0.055 (5) | 0.056 (5) | 0.043 (4) | 0.007 (4) | 0.017 (4) | 0.004 (4) |
| C30 | 0.052 (5) | 0.046 (5) | 0.048 (5) | 0.013 (4) | 0.021 (4) | 0.010 (4) |
| O31 | 0.071 (3) | 0.070 (3) | 0.064 (3) | −0.015 (3) | 0.025 (3) | −0.010 (3) |
| O32 | 0.080 (4) | 0.076 (4) | 0.065 (3) | −0.010 (3) | 0.041 (3) | 0.000 (3) |
| N33 | 0.051 (3) | 0.070 (4) | 0.046 (3) | 0.009 (3) | 0.016 (3) | −0.011 (3) |
| S34 | 0.0712 (13) | 0.0507 (13) | 0.0499 (11) | −0.0118 (10) | 0.0194 (10) | −0.0137 (10) |
| O35 | 0.088 (4) | 0.042 (3) | 0.079 (3) | −0.022 (3) | 0.029 (3) | −0.008 (3) |
| O36 | 0.101 (4) | 0.064 (3) | 0.056 (3) | −0.014 (3) | 0.037 (3) | −0.017 (3) |
| C37 | 0.055 (5) | 0.047 (5) | 0.038 (4) | −0.011 (3) | 0.013 (4) | −0.002 (4) |
| C38 | 0.064 (5) | 0.052 (5) | 0.062 (5) | −0.010 (4) | 0.024 (4) | 0.024 (4) |
| C39 | 0.052 (5) | 0.067 (5) | 0.062 (5) | 0.007 (4) | 0.027 (4) | 0.026 (4) |
| C40 | 0.041 (4) | 0.065 (5) | 0.045 (4) | −0.001 (4) | 0.015 (4) | 0.008 (4) |
| C41 | 0.058 (5) | 0.065 (6) | 0.038 (4) | −0.002 (4) | 0.014 (4) | 0.010 (4) |
| C42 | 0.063 (5) | 0.059 (5) | 0.042 (4) | −0.004 (4) | 0.025 (4) | −0.012 (4) |
| N43 | 0.058 (4) | 0.062 (4) | 0.045 (3) | 0.003 (3) | 0.012 (3) | 0.019 (3) |
| C44 | 0.047 (4) | 0.066 (6) | 0.048 (5) | −0.021 (4) | 0.013 (4) | −0.005 (4) |
| O45 | 0.098 (4) | 0.065 (4) | 0.050 (3) | −0.020 (3) | 0.036 (3) | −0.006 (3) |
| C46 | 0.057 (5) | 0.084 (6) | 0.066 (5) | 0.004 (5) | 0.014 (4) | −0.015 (5) |
| C1—C2 | 1.387 (8) | C24—C29 | 1.389 (8) |
| C1—C6 | 1.389 (9) | C24—C25 | 1.403 (8) |
| C1—C7 | 1.482 (8) | C24—C30 | 1.450 (8) |
| C2—C3 | 1.379 (8) | C25—C26 | 1.399 (8) |
| C2—N10 | 1.412 (7) | C25—N33 | 1.402 (7) |
| C3—C4 | 1.356 (9) | C26—C27 | 1.370 (8) |
| C3—H3 | 0.93 | C26—H26 | 0.93 |
| C4—C5 | 1.378 (9) | C27—C28 | 1.386 (9) |
| C4—H4 | 0.93 | C27—H27 | 0.93 |
| C5—C6 | 1.374 (9) | C28—C29 | 1.372 (9) |
| C5—H5 | 0.93 | C28—H28 | 0.93 |
| C6—H6 | 0.93 | C29—H29 | 0.93 |
| C7—O8 | 1.206 (7) | C30—O32 | 1.215 (7) |
| C7—O9 | 1.322 (7) | C30—O31 | 1.332 (8) |
| O9—H9 | 0.82 | O31—H31 | 0.82 |
| N10—S11 | 1.611 (5) | N33—S34 | 1.641 (5) |
| N10—H10 | 0.86 | N33—H33 | 0.86 |
| S11—O13 | 1.415 (4) | S34—O35 | 1.429 (4) |
| S11—O12 | 1.423 (4) | S34—O36 | 1.438 (4) |
| S11—C14 | 1.754 (6) | S34—C37 | 1.758 (7) |
| C14—C19 | 1.380 (7) | C37—C38 | 1.358 (8) |
| C14—C15 | 1.382 (8) | C37—C42 | 1.366 (8) |
| C15—C16 | 1.355 (8) | C38—C39 | 1.371 (9) |
| C15—H15 | 0.93 | C38—H38 | 0.93 |
| C16—C17 | 1.386 (7) | C39—C40 | 1.383 (8) |
| C16—H16 | 0.93 | C39—H39 | 0.93 |
| C17—C18 | 1.348 (8) | C40—C41 | 1.385 (8) |
| C17—N20 | 1.414 (7) | C40—N43 | 1.412 (7) |
| C18—C19 | 1.382 (8) | C41—C42 | 1.363 (8) |
| C18—H18 | 0.93 | C41—H41 | 0.93 |
| C19—H19 | 0.93 | C42—H42 | 0.93 |
| N20—C21 | 1.340 (7) | N43—C44 | 1.385 (8) |
| N20—H20 | 0.86 | N43—H43 | 0.86 |
| C21—O22 | 1.244 (6) | C44—O45 | 1.224 (7) |
| C21—C23 | 1.497 (8) | C44—C46 | 1.503 (9) |
| C23—H23A | 0.96 | C46—H46A | 0.96 |
| C23—H23B | 0.96 | C46—H46B | 0.96 |
| C23—H23C | 0.96 | C46—H46C | 0.96 |
| C2—C1—C6 | 118.9 (7) | C29—C24—C25 | 118.1 (6) |
| C2—C1—C7 | 120.8 (6) | C29—C24—C30 | 120.7 (7) |
| C6—C1—C7 | 120.3 (7) | C25—C24—C30 | 121.2 (6) |
| C3—C2—C1 | 119.3 (6) | C26—C25—N33 | 120.9 (6) |
| C3—C2—N10 | 120.8 (6) | C26—C25—C24 | 119.5 (6) |
| C1—C2—N10 | 119.8 (6) | N33—C25—C24 | 119.6 (6) |
| C4—C3—C2 | 122.3 (7) | C27—C26—C25 | 120.4 (6) |
| C4—C3—H3 | 118.9 | C27—C26—H26 | 119.8 |
| C2—C3—H3 | 118.9 | C25—C26—H26 | 119.8 |
| C3—C4—C5 | 118.2 (8) | C26—C27—C28 | 120.7 (7) |
| C3—C4—H4 | 120.9 | C26—C27—H27 | 119.7 |
| C5—C4—H4 | 120.9 | C28—C27—H27 | 119.7 |
| C6—C5—C4 | 121.3 (7) | C29—C28—C27 | 118.8 (7) |
| C6—C5—H5 | 119.3 | C29—C28—H28 | 120.6 |
| C4—C5—H5 | 119.3 | C27—C28—H28 | 120.6 |
| C5—C6—C1 | 119.9 (7) | C28—C29—C24 | 122.4 (7) |
| C5—C6—H6 | 120.1 | C28—C29—H29 | 118.8 |
| C1—C6—H6 | 120.1 | C24—C29—H29 | 118.8 |
| O8—C7—O9 | 121.3 (6) | O32—C30—O31 | 120.0 (6) |
| O8—C7—C1 | 125.3 (6) | O32—C30—C24 | 125.8 (7) |
| O9—C7—C1 | 113.4 (6) | O31—C30—C24 | 114.2 (6) |
| C7—O9—H9 | 109.5 | C30—O31—H31 | 109.5 |
| C2—N10—S11 | 125.8 (4) | C25—N33—S34 | 124.4 (4) |
| C2—N10—H10 | 117.1 | C25—N33—H33 | 117.8 |
| S11—N10—H10 | 117.1 | S34—N33—H33 | 117.8 |
| O13—S11—O12 | 117.5 (3) | O35—S34—O36 | 119.3 (3) |
| O13—S11—N10 | 112.5 (3) | O35—S34—N33 | 109.3 (3) |
| O12—S11—N10 | 103.2 (3) | O36—S34—N33 | 103.7 (3) |
| O13—S11—C14 | 107.3 (3) | O35—S34—C37 | 107.7 (3) |
| O12—S11—C14 | 109.7 (3) | O36—S34—C37 | 109.1 (3) |
| N10—S11—C14 | 106.0 (3) | N33—S34—C37 | 107.1 (3) |
| C19—C14—C15 | 119.9 (6) | C38—C37—C42 | 119.3 (6) |
| C19—C14—S11 | 119.9 (5) | C38—C37—S34 | 119.4 (6) |
| C15—C14—S11 | 119.9 (5) | C42—C37—S34 | 121.2 (5) |
| C16—C15—C14 | 119.0 (6) | C37—C38—C39 | 122.1 (6) |
| C16—C15—H15 | 120.5 | C37—C38—H38 | 118.9 |
| C14—C15—H15 | 120.5 | C39—C38—H38 | 118.9 |
| C15—C16—C17 | 121.7 (6) | C38—C39—C40 | 117.8 (6) |
| C15—C16—H16 | 119.2 | C38—C39—H39 | 121.1 |
| C17—C16—H16 | 119.2 | C40—C39—H39 | 121.1 |
| C18—C17—C16 | 119.2 (6) | C39—C40—C41 | 120.6 (7) |
| C18—C17—N20 | 124.7 (5) | C39—C40—N43 | 122.2 (6) |
| C16—C17—N20 | 116.1 (5) | C41—C40—N43 | 117.2 (6) |
| C17—C18—C19 | 120.5 (6) | C42—C41—C40 | 119.3 (6) |
| C17—C18—H18 | 119.7 | C42—C41—H41 | 120.3 |
| C19—C18—H18 | 119.7 | C40—C41—H41 | 120.3 |
| C14—C19—C18 | 119.7 (6) | C41—C42—C37 | 120.8 (6) |
| C14—C19—H19 | 120.1 | C41—C42—H42 | 119.6 |
| C18—C19—H19 | 120.1 | C37—C42—H42 | 119.6 |
| C21—N20—C17 | 130.0 (5) | C44—N43—C40 | 128.8 (6) |
| C21—N20—H20 | 115 | C44—N43—H43 | 115.6 |
| C17—N20—H20 | 115 | C40—N43—H43 | 115.6 |
| O22—C21—N20 | 121.9 (6) | O45—C44—N43 | 121.7 (7) |
| O22—C21—C23 | 121.6 (6) | O45—C44—C46 | 122.7 (7) |
| N20—C21—C23 | 116.5 (6) | N43—C44—C46 | 115.5 (6) |
| C21—C23—H23A | 109.5 | C44—C46—H46A | 109.5 |
| C21—C23—H23B | 109.5 | C44—C46—H46B | 109.5 |
| H23A—C23—H23B | 109.5 | H46A—C46—H46B | 109.5 |
| C21—C23—H23C | 109.5 | C44—C46—H46C | 109.5 |
| H23A—C23—H23C | 109.5 | H46A—C46—H46C | 109.5 |
| H23B—C23—H23C | 109.5 | H46B—C46—H46C | 109.5 |
| H··· | ||||
| O9—H9···O22i | 0.82 | 1.84 | 2.649 (6) | 168 |
| N10—H10···O8 | 0.86 | 2.13 | 2.624 (7) | 116 |
| N20—H20···O13ii | 0.86 | 2.24 | 3.073 (6) | 164 |
| O31—H31···O45iii | 0.82 | 1.81 | 2.623 (6) | 174 |
| N33—H33···O32 | 0.86 | 2.17 | 2.641 (7) | 114 |
| N43—H43···O36i | 0.86 | 2.11 | 2.958 (7) | 168 |
| C23—H23B···Cg1 | 0.96 | 2.74 | 3.6110 (15) | 151 |
| C46—H46C···Cg2 | 0.96 | 2.71 | 3.5821 (13) | 151 |
Hydrogen-bond geometry (Å, °)
Cg1 and Cg2 are the centroids of the C37–C42 and C14–C19 rings, respectively.
| H⋯ | ||||
|---|---|---|---|---|
| O9—H9⋯O22i | 0.82 | 1.84 | 2.649 (6) | 168 |
| N10—H10⋯O8 | 0.86 | 2.13 | 2.624 (7) | 116 |
| N20—H20⋯O13ii | 0.86 | 2.24 | 3.073 (6) | 164 |
| O31—H31⋯O45iii | 0.82 | 1.81 | 2.623 (6) | 174 |
| N33—H33⋯O32 | 0.86 | 2.17 | 2.641 (7) | 114 |
| N43—H43⋯O36i | 0.86 | 2.11 | 2.958 (7) | 168 |
| C23—H23 | 0.96 | 2.74 | 3.6110 (15) | 151 |
| C46—H46 | 0.96 | 2.71 | 3.5821 (13) | 151 |
Symmetry codes: (i) ; (ii) ; (iii) .