| Literature DB >> 21589548 |
J Kanchanadevi, V Dhayalan, A K Mohanakrishnan, G Anbalagan, G Chakkaravarthi, V Manivannan.
Abstract
In the title compound, C(24)H(17)NO(4)S, the phenyl ring makes a dihedral angle of 88.12 (5)° with the carbazole unit. The mol-ecular structure is stabilized by weak intra-molecular C-H⋯O inter-actions and the crystal packing exhibits weak inter-molecular C-H⋯O and C-H⋯π inter-actions. Two C atoms of the 2,3-dihydro-1,4-dioxine fragment are disordered over two positions with site-occupancy factors of 0.718 (11) and 0.282 (11).Entities:
Year: 2010 PMID: 21589548 PMCID: PMC3011594 DOI: 10.1107/S1600536810047343
Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN: 1600-5368
| C24H17NO4S | |
| Orthorhombic, | Mo |
| Hall symbol: -P 2ac 2ab | Cell parameters from 5557 reflections |
| θ = 2.3–27.8° | |
| µ = 0.20 mm−1 | |
| Block, colourless | |
| 0.26 × 0.22 × 0.20 mm |
| Bruker Kappa APEXII diffractometer | 4813 independent reflections |
| Radiation source: fine-focus sealed tube | 3469 reflections with |
| graphite | |
| ω and φ scans | θmax = 28.3°, θmin = 2.3° |
| Absorption correction: multi-scan ( | |
| 19551 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 | |
| 4813 reflections | (Δ/σ)max < 0.001 |
| 290 parameters | Δρmax = 0.28 e Å−3 |
| 1 restraint | Δρmin = −0.36 e Å−3 |
| Occ. (<1) | |||||
| S1 | 0.75886 (3) | 0.20738 (3) | 0.50676 (2) | 0.04410 (14) | |
| O1 | 0.68946 (12) | 0.14774 (9) | 0.48039 (8) | 0.0645 (4) | |
| O2 | 0.86322 (10) | 0.20175 (9) | 0.48726 (7) | 0.0609 (4) | |
| O3 | 1.18355 (9) | 0.45554 (8) | 0.71672 (8) | 0.0547 (3) | |
| O4 | 1.10235 (10) | 0.45229 (9) | 0.86231 (7) | 0.0614 (4) | |
| N1 | 0.75360 (10) | 0.20284 (8) | 0.59811 (8) | 0.0412 (3) | |
| C1 | 0.71502 (13) | 0.30481 (11) | 0.48204 (9) | 0.0429 (4) | |
| C2 | 0.61251 (14) | 0.32135 (13) | 0.48674 (10) | 0.0541 (5) | |
| H2 | 0.5677 | 0.2819 | 0.5041 | 0.065* | |
| C3 | 0.57779 (19) | 0.39686 (16) | 0.46545 (12) | 0.0728 (6) | |
| H3 | 0.5089 | 0.4087 | 0.4678 | 0.087* | |
| C4 | 0.6445 (3) | 0.45467 (16) | 0.44081 (14) | 0.0850 (7) | |
| H4 | 0.6205 | 0.5057 | 0.4266 | 0.102* | |
| C5 | 0.7463 (2) | 0.43862 (16) | 0.43669 (15) | 0.0840 (8) | |
| H5 | 0.7908 | 0.4788 | 0.4200 | 0.101* | |
| C6 | 0.78291 (17) | 0.36299 (14) | 0.45719 (12) | 0.0636 (6) | |
| H6 | 0.8518 | 0.3514 | 0.4544 | 0.076* | |
| C7 | 0.81876 (11) | 0.24936 (10) | 0.64551 (8) | 0.0348 (3) | |
| C8 | 0.90603 (11) | 0.29052 (10) | 0.62968 (8) | 0.0379 (3) | |
| H8 | 0.9320 | 0.2914 | 0.5818 | 0.046* | |
| C9 | 0.95611 (11) | 0.33194 (9) | 0.68816 (8) | 0.0343 (3) | |
| C10 | 1.04706 (12) | 0.37570 (10) | 0.67599 (9) | 0.0397 (4) | |
| H10 | 1.0742 | 0.3780 | 0.6284 | 0.048* | |
| C11 | 1.09563 (11) | 0.41443 (10) | 0.73221 (9) | 0.0396 (4) | |
| C12 | 1.2233 (3) | 0.5044 (3) | 0.7720 (3) | 0.0511 (10) | 0.718 (11) |
| H12A | 1.1901 | 0.5573 | 0.7710 | 0.061* | 0.718 (11) |
| H12B | 1.2950 | 0.5128 | 0.7631 | 0.061* | 0.718 (11) |
| C12A | 1.2432 (9) | 0.4744 (9) | 0.7890 (7) | 0.054 (3) | 0.282 (11) |
| H12C | 1.2765 | 0.4249 | 0.8057 | 0.064* | 0.282 (11) |
| H12D | 1.2956 | 0.5143 | 0.7780 | 0.064* | 0.282 (11) |
| C13 | 1.2089 (3) | 0.4664 (3) | 0.8461 (2) | 0.0523 (11) | 0.718 (11) |
| H13A | 1.2450 | 0.4147 | 0.8478 | 0.063* | 0.718 (11) |
| H13B | 1.2375 | 0.5018 | 0.8838 | 0.063* | 0.718 (11) |
| C13A | 1.1788 (7) | 0.5065 (9) | 0.8505 (5) | 0.054 (3) | 0.282 (11) |
| H13C | 1.2189 | 0.5128 | 0.8951 | 0.065* | 0.282 (11) |
| H13D | 1.1512 | 0.5595 | 0.8371 | 0.065* | 0.282 (11) |
| C14 | 1.05574 (12) | 0.41171 (10) | 0.80512 (9) | 0.0424 (4) | |
| C15 | 0.96920 (13) | 0.36957 (10) | 0.81897 (9) | 0.0428 (4) | |
| H15 | 0.9442 | 0.3674 | 0.8671 | 0.051* | |
| C16 | 0.91622 (11) | 0.32886 (10) | 0.76166 (8) | 0.0355 (3) | |
| C17 | 0.82565 (11) | 0.28589 (10) | 0.77520 (9) | 0.0385 (3) | |
| H17 | 0.7989 | 0.2837 | 0.8229 | 0.046* | |
| C18 | 0.77697 (11) | 0.24729 (9) | 0.71804 (8) | 0.0345 (3) | |
| C19 | 0.68351 (11) | 0.20045 (9) | 0.71441 (9) | 0.0369 (3) | |
| C20 | 0.61522 (12) | 0.17749 (11) | 0.76943 (10) | 0.0456 (4) | |
| H20 | 0.6249 | 0.1938 | 0.8183 | 0.055* | |
| C21 | 0.53295 (14) | 0.13020 (12) | 0.75009 (12) | 0.0569 (5) | |
| H21 | 0.4869 | 0.1139 | 0.7862 | 0.068* | |
| C22 | 0.51865 (14) | 0.10687 (13) | 0.67716 (13) | 0.0599 (5) | |
| H22 | 0.4619 | 0.0759 | 0.6650 | 0.072* | |
| C23 | 0.58604 (14) | 0.12802 (12) | 0.62164 (11) | 0.0540 (5) | |
| H23 | 0.5763 | 0.1112 | 0.5729 | 0.065* | |
| C24 | 0.66883 (12) | 0.17543 (10) | 0.64165 (9) | 0.0406 (4) |
| S1 | 0.0514 (2) | 0.0484 (3) | 0.0325 (2) | 0.00302 (18) | −0.00712 (17) | −0.00640 (17) |
| O1 | 0.0849 (10) | 0.0577 (9) | 0.0509 (8) | −0.0113 (7) | −0.0220 (7) | −0.0092 (7) |
| O2 | 0.0564 (8) | 0.0862 (11) | 0.0400 (7) | 0.0196 (7) | 0.0003 (6) | −0.0129 (7) |
| O3 | 0.0468 (6) | 0.0591 (8) | 0.0582 (8) | −0.0183 (6) | 0.0014 (6) | 0.0065 (6) |
| O4 | 0.0638 (8) | 0.0722 (9) | 0.0484 (8) | −0.0254 (7) | −0.0039 (6) | −0.0135 (7) |
| N1 | 0.0462 (7) | 0.0441 (8) | 0.0334 (7) | −0.0060 (6) | −0.0073 (5) | 0.0000 (6) |
| C1 | 0.0489 (9) | 0.0498 (10) | 0.0300 (8) | 0.0005 (8) | −0.0015 (7) | 0.0029 (7) |
| C2 | 0.0510 (10) | 0.0658 (12) | 0.0456 (10) | 0.0058 (9) | 0.0012 (8) | 0.0040 (9) |
| C3 | 0.0784 (14) | 0.0827 (16) | 0.0572 (13) | 0.0317 (11) | 0.0006 (11) | 0.0054 (11) |
| C4 | 0.129 (2) | 0.0613 (15) | 0.0647 (15) | 0.0263 (12) | 0.0033 (14) | 0.0147 (11) |
| C5 | 0.113 (2) | 0.0669 (16) | 0.0722 (17) | −0.0160 (15) | 0.0085 (14) | 0.0251 (13) |
| C6 | 0.0626 (11) | 0.0692 (14) | 0.0588 (13) | −0.0094 (10) | 0.0055 (10) | 0.0160 (10) |
| C7 | 0.0390 (7) | 0.0341 (8) | 0.0313 (8) | 0.0031 (6) | −0.0038 (6) | −0.0002 (6) |
| C8 | 0.0414 (8) | 0.0449 (9) | 0.0275 (7) | −0.0010 (7) | 0.0033 (6) | 0.0006 (7) |
| C9 | 0.0365 (7) | 0.0359 (8) | 0.0304 (8) | 0.0018 (6) | 0.0033 (6) | 0.0012 (6) |
| C10 | 0.0427 (8) | 0.0435 (9) | 0.0329 (8) | −0.0023 (7) | 0.0065 (6) | 0.0039 (7) |
| C11 | 0.0379 (7) | 0.0352 (8) | 0.0456 (9) | −0.0025 (6) | 0.0013 (6) | 0.0051 (7) |
| C12 | 0.0400 (17) | 0.047 (2) | 0.066 (3) | −0.0101 (15) | −0.0075 (15) | −0.0009 (18) |
| C12A | 0.053 (5) | 0.051 (6) | 0.057 (6) | −0.002 (4) | −0.019 (4) | −0.005 (5) |
| C13 | 0.0498 (17) | 0.049 (2) | 0.058 (2) | −0.0055 (16) | −0.0143 (15) | −0.0046 (17) |
| C13A | 0.045 (4) | 0.048 (6) | 0.070 (5) | −0.003 (4) | −0.010 (3) | −0.007 (4) |
| C14 | 0.0490 (9) | 0.0400 (9) | 0.0383 (9) | −0.0039 (7) | −0.0035 (7) | −0.0036 (7) |
| C15 | 0.0494 (9) | 0.0476 (10) | 0.0314 (8) | −0.0075 (7) | 0.0058 (7) | −0.0049 (7) |
| C16 | 0.0389 (7) | 0.0356 (8) | 0.0321 (8) | 0.0010 (6) | 0.0040 (6) | −0.0014 (6) |
| C17 | 0.0427 (8) | 0.0420 (9) | 0.0308 (8) | −0.0030 (7) | 0.0075 (6) | −0.0014 (7) |
| C18 | 0.0359 (7) | 0.0311 (8) | 0.0364 (8) | 0.0017 (6) | 0.0027 (6) | 0.0013 (6) |
| C19 | 0.0357 (7) | 0.0312 (8) | 0.0438 (9) | 0.0023 (6) | −0.0007 (6) | 0.0037 (7) |
| C20 | 0.0417 (8) | 0.0439 (9) | 0.0513 (10) | −0.0004 (7) | 0.0059 (7) | 0.0032 (8) |
| C21 | 0.0424 (9) | 0.0562 (12) | 0.0721 (13) | −0.0059 (8) | 0.0055 (9) | 0.0094 (10) |
| C22 | 0.0437 (9) | 0.0555 (12) | 0.0805 (15) | −0.0141 (8) | −0.0105 (9) | 0.0095 (10) |
| C23 | 0.0534 (10) | 0.0525 (11) | 0.0561 (11) | −0.0090 (8) | −0.0173 (9) | 0.0040 (9) |
| C24 | 0.0407 (8) | 0.0345 (8) | 0.0466 (10) | 0.0011 (7) | −0.0075 (7) | 0.0063 (7) |
| S1—O1 | 1.4201 (14) | C10—H10 | 0.9300 |
| S1—O2 | 1.4237 (15) | C11—C14 | 1.417 (2) |
| S1—N1 | 1.6509 (15) | C12—C13 | 1.486 (7) |
| S1—C1 | 1.7535 (19) | C12—H12A | 0.9700 |
| O3—C11 | 1.3695 (19) | C12—H12B | 0.9700 |
| O3—C12 | 1.381 (4) | C12A—C13A | 1.492 (19) |
| O3—C12A | 1.555 (11) | C12A—H12C | 0.9700 |
| O4—C13A | 1.360 (8) | C12A—H12D | 0.9700 |
| O4—C14 | 1.372 (2) | C13—H13A | 0.9700 |
| O4—C13 | 1.454 (4) | C13—H13B | 0.9700 |
| N1—C7 | 1.4315 (19) | C13A—H13C | 0.9700 |
| N1—C24 | 1.438 (2) | C13A—H13D | 0.9700 |
| C1—C2 | 1.381 (2) | C14—C15 | 1.357 (2) |
| C1—C6 | 1.382 (3) | C15—C16 | 1.414 (2) |
| C2—C3 | 1.373 (3) | C15—H15 | 0.9300 |
| C2—H2 | 0.9300 | C16—C17 | 1.407 (2) |
| C3—C4 | 1.367 (4) | C17—C18 | 1.369 (2) |
| C3—H3 | 0.9300 | C17—H17 | 0.9300 |
| C4—C5 | 1.370 (4) | C18—C19 | 1.453 (2) |
| C4—H4 | 0.9300 | C19—C24 | 1.388 (2) |
| C5—C6 | 1.379 (3) | C19—C20 | 1.392 (2) |
| C5—H5 | 0.9300 | C20—C21 | 1.378 (3) |
| C6—H6 | 0.9300 | C20—H20 | 0.9300 |
| C7—C8 | 1.364 (2) | C21—C22 | 1.383 (3) |
| C7—C18 | 1.420 (2) | C21—H21 | 0.9300 |
| C8—C9 | 1.417 (2) | C22—C23 | 1.383 (3) |
| C8—H8 | 0.9300 | C22—H22 | 0.9300 |
| C9—C10 | 1.414 (2) | C23—C24 | 1.387 (2) |
| C9—C16 | 1.427 (2) | C23—H23 | 0.9300 |
| C10—C11 | 1.357 (2) | ||
| O1—S1—O2 | 119.73 (9) | C13A—C12A—O3 | 113.9 (9) |
| O1—S1—N1 | 106.04 (8) | C13A—C12A—H12C | 108.8 |
| O2—S1—N1 | 106.52 (7) | O3—C12A—H12C | 108.8 |
| O1—S1—C1 | 109.09 (9) | C13A—C12A—H12D | 108.8 |
| O2—S1—C1 | 108.35 (9) | O3—C12A—H12D | 108.8 |
| N1—S1—C1 | 106.32 (8) | H12C—C12A—H12D | 107.7 |
| C11—O3—C12 | 117.3 (2) | O4—C13—C12 | 111.7 (4) |
| C11—O3—C12A | 110.8 (5) | O4—C13—H13A | 109.3 |
| C13A—O4—C14 | 122.0 (4) | C12—C13—H13A | 109.3 |
| C14—O4—C13 | 111.0 (2) | O4—C13—H13B | 109.3 |
| C7—N1—C24 | 107.84 (13) | C12—C13—H13B | 109.3 |
| C7—N1—S1 | 123.16 (11) | H13A—C13—H13B | 107.9 |
| C24—N1—S1 | 126.29 (11) | O4—C13A—C12A | 108.0 (10) |
| C2—C1—C6 | 121.28 (19) | O4—C13A—H13C | 110.1 |
| C2—C1—S1 | 119.03 (15) | C12A—C13A—H13C | 110.1 |
| C6—C1—S1 | 119.69 (15) | O4—C13A—H13D | 110.1 |
| C3—C2—C1 | 119.1 (2) | C12A—C13A—H13D | 110.1 |
| C3—C2—H2 | 120.5 | H13C—C13A—H13D | 108.4 |
| C1—C2—H2 | 120.5 | C15—C14—O4 | 118.97 (15) |
| C4—C3—C2 | 119.9 (2) | C15—C14—C11 | 119.94 (15) |
| C4—C3—H3 | 120.0 | O4—C14—C11 | 121.08 (15) |
| C2—C3—H3 | 120.0 | C14—C15—C16 | 121.36 (15) |
| C3—C4—C5 | 121.1 (2) | C14—C15—H15 | 119.3 |
| C3—C4—H4 | 119.5 | C16—C15—H15 | 119.3 |
| C5—C4—H4 | 119.5 | C17—C16—C15 | 121.85 (14) |
| C4—C5—C6 | 120.0 (2) | C17—C16—C9 | 119.45 (14) |
| C4—C5—H5 | 120.0 | C15—C16—C9 | 118.70 (14) |
| C6—C5—H5 | 120.0 | C18—C17—C16 | 119.86 (14) |
| C5—C6—C1 | 118.6 (2) | C18—C17—H17 | 120.1 |
| C5—C6—H6 | 120.7 | C16—C17—H17 | 120.1 |
| C1—C6—H6 | 120.7 | C17—C18—C7 | 120.05 (14) |
| C8—C7—C18 | 122.16 (14) | C17—C18—C19 | 132.47 (14) |
| C8—C7—N1 | 130.11 (14) | C7—C18—C19 | 107.48 (13) |
| C18—C7—N1 | 107.73 (13) | C24—C19—C20 | 120.28 (15) |
| C7—C8—C9 | 118.27 (14) | C24—C19—C18 | 108.45 (14) |
| C7—C8—H8 | 120.9 | C20—C19—C18 | 131.24 (15) |
| C9—C8—H8 | 120.9 | C21—C20—C19 | 118.73 (18) |
| C10—C9—C8 | 121.46 (14) | C21—C20—H20 | 120.6 |
| C10—C9—C16 | 118.34 (14) | C19—C20—H20 | 120.6 |
| C8—C9—C16 | 120.18 (14) | C20—C21—C22 | 120.22 (18) |
| C11—C10—C9 | 121.40 (15) | C20—C21—H21 | 119.9 |
| C11—C10—H10 | 119.3 | C22—C21—H21 | 119.9 |
| C9—C10—H10 | 119.3 | C21—C22—C23 | 122.16 (17) |
| C10—C11—O3 | 118.47 (15) | C21—C22—H22 | 118.9 |
| C10—C11—C14 | 120.25 (14) | C23—C22—H22 | 118.9 |
| O3—C11—C14 | 121.27 (15) | C22—C23—C24 | 117.21 (18) |
| O3—C12—C13 | 111.0 (4) | C22—C23—H23 | 121.4 |
| O3—C12—H12A | 109.4 | C24—C23—H23 | 121.4 |
| C13—C12—H12A | 109.4 | C23—C24—C19 | 121.38 (16) |
| O3—C12—H12B | 109.4 | C23—C24—N1 | 130.11 (16) |
| C13—C12—H12B | 109.4 | C19—C24—N1 | 108.42 (13) |
| H12A—C12—H12B | 108.0 | ||
| O1—S1—N1—C7 | 174.92 (13) | O3—C12A—C13A—O4 | 55.0 (17) |
| O2—S1—N1—C7 | 46.36 (15) | C13A—O4—C14—C15 | −168.7 (8) |
| C1—S1—N1—C7 | −69.05 (14) | C13—O4—C14—C15 | 158.0 (3) |
| O1—S1—N1—C24 | −26.04 (16) | C13A—O4—C14—C11 | 10.2 (8) |
| O2—S1—N1—C24 | −154.61 (14) | C13—O4—C14—C11 | −23.1 (3) |
| C1—S1—N1—C24 | 89.99 (15) | C10—C11—C14—C15 | 0.6 (3) |
| O1—S1—C1—C2 | 39.85 (17) | O3—C11—C14—C15 | −179.12 (16) |
| O2—S1—C1—C2 | 171.74 (14) | C10—C11—C14—O4 | −178.27 (16) |
| N1—S1—C1—C2 | −74.10 (15) | O3—C11—C14—O4 | 2.0 (3) |
| O1—S1—C1—C6 | −139.10 (16) | O4—C14—C15—C16 | 177.91 (16) |
| O2—S1—C1—C6 | −7.21 (17) | C11—C14—C15—C16 | −1.0 (3) |
| N1—S1—C1—C6 | 106.94 (16) | C14—C15—C16—C17 | −179.13 (16) |
| C6—C1—C2—C3 | 0.7 (3) | C14—C15—C16—C9 | 0.7 (2) |
| S1—C1—C2—C3 | −178.21 (16) | C10—C9—C16—C17 | 179.83 (15) |
| C1—C2—C3—C4 | −0.7 (3) | C8—C9—C16—C17 | −1.4 (2) |
| C2—C3—C4—C5 | 0.2 (4) | C10—C9—C16—C15 | 0.0 (2) |
| C3—C4—C5—C6 | 0.4 (4) | C8—C9—C16—C15 | 178.78 (15) |
| C4—C5—C6—C1 | −0.3 (4) | C15—C16—C17—C18 | −179.92 (15) |
| C2—C1—C6—C5 | −0.2 (3) | C9—C16—C17—C18 | 0.3 (2) |
| S1—C1—C6—C5 | 178.73 (18) | C16—C17—C18—C7 | 1.1 (2) |
| C24—N1—C7—C8 | −177.15 (16) | C16—C17—C18—C19 | −178.74 (16) |
| S1—N1—C7—C8 | −14.8 (2) | C8—C7—C18—C17 | −1.5 (2) |
| C24—N1—C7—C18 | 2.68 (17) | N1—C7—C18—C17 | 178.69 (14) |
| S1—N1—C7—C18 | 165.04 (11) | C8—C7—C18—C19 | 178.43 (14) |
| C18—C7—C8—C9 | 0.3 (2) | N1—C7—C18—C19 | −1.41 (16) |
| N1—C7—C8—C9 | −179.87 (15) | C17—C18—C19—C24 | 179.46 (17) |
| C7—C8—C9—C10 | 179.83 (15) | C7—C18—C19—C24 | −0.42 (17) |
| C7—C8—C9—C16 | 1.1 (2) | C17—C18—C19—C20 | −2.7 (3) |
| C8—C9—C10—C11 | −179.13 (15) | C7—C18—C19—C20 | 177.44 (16) |
| C16—C9—C10—C11 | −0.4 (2) | C24—C19—C20—C21 | −0.4 (2) |
| C9—C10—C11—O3 | 179.82 (14) | C18—C19—C20—C21 | −178.10 (16) |
| C9—C10—C11—C14 | 0.1 (2) | C19—C20—C21—C22 | −0.5 (3) |
| C12—O3—C11—C10 | 170.5 (3) | C20—C21—C22—C23 | 1.4 (3) |
| C12A—O3—C11—C10 | −164.0 (6) | C21—C22—C23—C24 | −1.1 (3) |
| C12—O3—C11—C14 | −9.7 (3) | C22—C23—C24—C19 | 0.1 (3) |
| C12A—O3—C11—C14 | 15.8 (6) | C22—C23—C24—N1 | 176.05 (17) |
| C11—O3—C12—C13 | 37.2 (6) | C20—C19—C24—C23 | 0.7 (2) |
| C12A—O3—C12—C13 | −42.9 (14) | C18—C19—C24—C23 | 178.81 (15) |
| C11—O3—C12A—C13A | −44.9 (14) | C20—C19—C24—N1 | −176.06 (14) |
| C12—O3—C12A—C13A | 65.6 (16) | C18—C19—C24—N1 | 2.09 (17) |
| C13A—O4—C13—C12 | −66.6 (9) | C7—N1—C24—C23 | −179.30 (17) |
| C14—O4—C13—C12 | 50.7 (5) | S1—N1—C24—C23 | 19.0 (3) |
| O3—C12—C13—O4 | −59.1 (7) | C7—N1—C24—C19 | −2.97 (17) |
| C14—O4—C13A—C12A | −37.8 (15) | S1—N1—C24—C19 | −164.63 (12) |
| C13—O4—C13A—C12A | 40.2 (10) |
| Cg1, Cg4, Cg5 and Cg7 are the centroids of the N1/C7/C18/C19/C24, C1–C6, C7–C9/C16–C18 and C19–C24 rings, respectively. |
| H··· | ||||
| C6—H6···O2 | 0.93 | 2.52 | 2.894 (3) | 104 |
| C8—H8···O2 | 0.93 | 2.42 | 3.005 (2) | 120 |
| C23—H23···O1 | 0.93 | 2.32 | 2.908 (3) | 121 |
| C10—H10···O1i | 0.93 | 2.52 | 3.411 (2) | 161 |
| C12—H12A···Cg1ii | 0.97 | 2.98 | 3.670 (5) | 129 |
| C12—H12B···Cg7ii | 0.97 | 2.78 | 3.411 (5) | 124 |
| C13—H13A···Cg5iii | 0.97 | 2.77 | 3.680 (5) | 157 |
| C20—H20···Cg4iv | 0.93 | 2.94 | 3.689 (2) | 138 |
| C12A—H12C···Cg5iii | 0.97 | 2.53 | 3.446 (14) | 158 |
| C12A—H12D···Cg7ii | 0.97 | 2.69 | 3.585 (14) | 153 |
| C13A—H13D···Cg1ii | 0.97 | 2.92 | 3.585 (14) | 127 |
Hydrogen-bond geometry (Å, °)
Cg1, Cg4, Cg5 and Cg7 are the centroids of the N1/C7/C18/C19/C24, C1–C6, C7–C9/C16–C18 and C19–C24 rings, respectively.
| H⋯ | ||||
|---|---|---|---|---|
| C8—H8⋯O2 | 0.93 | 2.42 | 3.005 (2) | 120 |
| C23—H23⋯O1 | 0.93 | 2.32 | 2.908 (3) | 121 |
| C10—H10⋯O1i | 0.93 | 2.52 | 3.411 (2) | 161 |
| C12—H12 | 0.97 | 2.98 | 3.670 (5) | 129 |
| C12—H12 | 0.97 | 2.78 | 3.411 (5) | 124 |
| C13—H13 | 0.97 | 2.77 | 3.680 (5) | 157 |
| C20—H20⋯ | 0.93 | 2.94 | 3.689 (2) | 138 |
| C12 | 0.97 | 2.53 | 3.446 (14) | 158 |
| C12 | 0.97 | 2.69 | 3.585 (14) | 153 |
| C13 | 0.97 | 2.92 | 3.585 (14) | 127 |
Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .