| Literature DB >> 22199864 |
Hoong-Kun Fun, Suhana Arshad, S Samshuddin, B Narayana, B K Sarojini.
Abstract
In the title compound, C(25)H(21)F(2)N(3)O(3)S, the morpholine ring adopts a chair conformation. The 1,3,4-oxadiazole-2(3H)-thione group makes dihedral angles of 78.69 (8), 53.56 (7) and 55.30 (9)° with the benzene rings. In the crystal, O-H⋯O, C-H⋯S and C-H⋯F hydrogen bonds linked the mol-ecules into layers lying parallel to the ab plane. Weak C-H⋯π inter-actions also occur.Entities:
Year: 2011 PMID: 22199864 PMCID: PMC3239015 DOI: 10.1107/S1600536811048471
Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN: 1600-5368
| C25H21F2N3O3S | |
| Monoclinic, | Mo |
| Hall symbol: -C 2yc | Cell parameters from 6002 reflections |
| θ = 2.3–27.3° | |
| µ = 0.19 mm−1 | |
| β = 94.202 (2)° | Block, colourless |
| 0.48 × 0.25 × 0.17 mm | |
| Bruker SMART APEXII DUO CCD area-detector diffractometer | 6182 independent reflections |
| Radiation source: fine-focus sealed tube | 4139 reflections with |
| graphite | |
| φ and ω scans | θmax = 29.1°, θmin = 1.6° |
| Absorption correction: multi-scan ( | |
| 23057 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 atoms treated by a mixture of independent and constrained refinement | |
| 6182 reflections | (Δ/σ)max < 0.001 |
| 311 parameters | Δρmax = 0.24 e Å−3 |
| 0 restraints | Δρmin = −0.24 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 |
| S1 | 0.15583 (3) | 0.82030 (5) | 0.44595 (2) | 0.06259 (17) | |
| F1 | 0.77333 (9) | 0.33903 (13) | 0.20221 (6) | 0.0943 (5) | |
| F2 | 0.46943 (11) | 1.25156 (10) | 0.31200 (6) | 0.1043 (5) | |
| O1 | 0.29532 (7) | 0.74319 (10) | 0.40602 (4) | 0.0469 (3) | |
| O2 | 0.38526 (11) | 1.29292 (12) | 0.42547 (7) | 0.0812 (5) | |
| O3 | 0.39200 (10) | 0.53070 (12) | 0.41580 (6) | 0.0697 (5) | |
| N1 | 0.39553 (9) | 0.85596 (11) | 0.44436 (5) | 0.0439 (3) | |
| N2 | 0.31768 (8) | 0.88887 (11) | 0.45963 (5) | 0.0420 (3) | |
| N3 | 0.32987 (9) | 1.09806 (11) | 0.48147 (6) | 0.0462 (3) | |
| C1 | 0.64272 (12) | 0.56922 (18) | 0.24724 (7) | 0.0583 (5) | |
| H1A | 0.6243 | 0.6433 | 0.2366 | 0.070* | |
| C2 | 0.69619 (13) | 0.5084 (2) | 0.21659 (8) | 0.0673 (6) | |
| H2A | 0.7141 | 0.5411 | 0.1858 | 0.081* | |
| C3 | 0.72171 (12) | 0.4003 (2) | 0.23261 (8) | 0.0616 (5) | |
| C4 | 0.69747 (13) | 0.34894 (18) | 0.27745 (9) | 0.0635 (5) | |
| H4A | 0.7161 | 0.2744 | 0.2873 | 0.076* | |
| C5 | 0.64462 (12) | 0.41028 (16) | 0.30795 (8) | 0.0569 (5) | |
| H5A | 0.6277 | 0.3764 | 0.3388 | 0.068* | |
| C6 | 0.61605 (10) | 0.52180 (14) | 0.29362 (6) | 0.0456 (4) | |
| C7 | 0.55723 (10) | 0.58586 (14) | 0.32581 (6) | 0.0451 (4) | |
| C8 | 0.50339 (11) | 0.52572 (14) | 0.35719 (7) | 0.0504 (4) | |
| H8A | 0.5062 | 0.4445 | 0.3594 | 0.061* | |
| C9 | 0.44575 (11) | 0.58574 (14) | 0.38513 (7) | 0.0498 (4) | |
| C10 | 0.43949 (10) | 0.70772 (13) | 0.38186 (6) | 0.0432 (4) | |
| C11 | 0.49340 (10) | 0.76946 (13) | 0.35017 (6) | 0.0428 (4) | |
| C12 | 0.55155 (11) | 0.70777 (14) | 0.32334 (7) | 0.0473 (4) | |
| H12A | 0.5878 | 0.7488 | 0.3031 | 0.057* | |
| C13 | 0.48645 (11) | 0.89862 (13) | 0.34198 (6) | 0.0442 (4) | |
| C14 | 0.41390 (13) | 0.94776 (16) | 0.31948 (8) | 0.0605 (5) | |
| H14A | 0.3680 | 0.8998 | 0.3111 | 0.073* | |
| C15 | 0.40759 (16) | 1.06664 (18) | 0.30901 (9) | 0.0715 (6) | |
| H15A | 0.3585 | 1.0987 | 0.2935 | 0.086* | |
| C16 | 0.47502 (17) | 1.13499 (16) | 0.32200 (9) | 0.0669 (6) | |
| C17 | 0.54758 (16) | 1.09168 (18) | 0.34457 (10) | 0.0725 (6) | |
| H17A | 0.5925 | 1.1412 | 0.3533 | 0.087* | |
| C18 | 0.55406 (13) | 0.97158 (16) | 0.35447 (8) | 0.0591 (5) | |
| H18A | 0.6038 | 0.9405 | 0.3695 | 0.071* | |
| C19 | 0.37959 (10) | 0.77082 (13) | 0.41218 (6) | 0.0410 (3) | |
| C20 | 0.25662 (11) | 0.82095 (14) | 0.43819 (6) | 0.0434 (4) | |
| C21 | 0.30977 (12) | 0.98278 (14) | 0.49890 (7) | 0.0497 (4) | |
| H21A | 0.2528 | 0.9833 | 0.5093 | 0.060* | |
| H21B | 0.3460 | 0.9643 | 0.5301 | 0.060* | |
| C22 | 0.28404 (13) | 1.13579 (17) | 0.43316 (8) | 0.0602 (5) | |
| H22A | 0.2249 | 1.1204 | 0.4352 | 0.072* | |
| H22B | 0.3030 | 1.0927 | 0.4033 | 0.072* | |
| C23 | 0.29823 (15) | 1.26587 (18) | 0.42564 (9) | 0.0719 (6) | |
| H23A | 0.2698 | 1.2908 | 0.3925 | 0.086* | |
| H23B | 0.2744 | 1.3088 | 0.4539 | 0.086* | |
| C24 | 0.42904 (15) | 1.25413 (18) | 0.47370 (12) | 0.0814 (7) | |
| H24A | 0.4074 | 1.2946 | 0.5034 | 0.098* | |
| H24B | 0.4879 | 1.2729 | 0.4731 | 0.098* | |
| C25 | 0.41867 (12) | 1.12362 (16) | 0.48025 (10) | 0.0644 (5) | |
| H25A | 0.4414 | 1.0825 | 0.4510 | 0.077* | |
| H25B | 0.4484 | 1.0978 | 0.5129 | 0.077* | |
| H1O3 | 0.3975 (15) | 0.462 (2) | 0.4167 (10) | 0.085 (8)* |
| S1 | 0.0450 (3) | 0.0795 (4) | 0.0650 (3) | −0.0045 (2) | 0.0151 (2) | 0.0078 (2) |
| F1 | 0.0814 (9) | 0.1175 (12) | 0.0876 (9) | 0.0413 (8) | 0.0312 (7) | −0.0178 (8) |
| F2 | 0.1615 (16) | 0.0372 (6) | 0.1162 (11) | −0.0069 (7) | 0.0247 (11) | 0.0151 (7) |
| O1 | 0.0495 (7) | 0.0439 (6) | 0.0489 (6) | −0.0027 (5) | 0.0138 (5) | −0.0051 (5) |
| O2 | 0.0963 (12) | 0.0428 (7) | 0.1116 (12) | 0.0026 (7) | 0.0566 (10) | 0.0151 (8) |
| O3 | 0.0916 (11) | 0.0357 (7) | 0.0894 (10) | −0.0003 (7) | 0.0576 (9) | 0.0079 (6) |
| N1 | 0.0444 (7) | 0.0367 (7) | 0.0522 (7) | −0.0046 (5) | 0.0149 (6) | −0.0034 (6) |
| N2 | 0.0448 (8) | 0.0333 (6) | 0.0500 (7) | −0.0026 (5) | 0.0170 (6) | −0.0023 (5) |
| N3 | 0.0476 (8) | 0.0344 (7) | 0.0585 (8) | 0.0001 (6) | 0.0167 (6) | −0.0009 (6) |
| C1 | 0.0570 (11) | 0.0596 (11) | 0.0609 (10) | 0.0109 (9) | 0.0209 (9) | 0.0060 (9) |
| C2 | 0.0602 (13) | 0.0873 (15) | 0.0574 (10) | 0.0148 (11) | 0.0241 (9) | 0.0043 (10) |
| C3 | 0.0450 (10) | 0.0789 (14) | 0.0621 (11) | 0.0153 (9) | 0.0114 (8) | −0.0157 (10) |
| C4 | 0.0587 (12) | 0.0581 (11) | 0.0748 (13) | 0.0153 (9) | 0.0117 (10) | −0.0077 (10) |
| C5 | 0.0599 (11) | 0.0527 (10) | 0.0597 (10) | 0.0059 (8) | 0.0163 (9) | 0.0002 (8) |
| C6 | 0.0416 (9) | 0.0453 (9) | 0.0509 (8) | 0.0004 (7) | 0.0105 (7) | −0.0044 (7) |
| C7 | 0.0450 (9) | 0.0416 (8) | 0.0501 (8) | −0.0016 (7) | 0.0129 (7) | −0.0034 (7) |
| C8 | 0.0615 (11) | 0.0322 (8) | 0.0603 (10) | 0.0012 (7) | 0.0230 (8) | 0.0000 (7) |
| C9 | 0.0603 (11) | 0.0364 (8) | 0.0557 (9) | −0.0037 (7) | 0.0249 (8) | 0.0004 (7) |
| C10 | 0.0481 (9) | 0.0341 (8) | 0.0492 (8) | −0.0036 (6) | 0.0165 (7) | −0.0048 (6) |
| C11 | 0.0440 (9) | 0.0343 (8) | 0.0513 (8) | −0.0074 (6) | 0.0123 (7) | −0.0036 (6) |
| C12 | 0.0454 (9) | 0.0416 (8) | 0.0569 (9) | −0.0088 (7) | 0.0179 (8) | −0.0020 (7) |
| C13 | 0.0510 (10) | 0.0348 (8) | 0.0488 (8) | −0.0092 (7) | 0.0174 (7) | −0.0038 (6) |
| C14 | 0.0619 (12) | 0.0458 (10) | 0.0732 (12) | −0.0109 (9) | 0.0013 (10) | 0.0040 (9) |
| C15 | 0.0857 (16) | 0.0513 (11) | 0.0769 (13) | 0.0032 (11) | 0.0012 (12) | 0.0133 (10) |
| C16 | 0.0993 (17) | 0.0350 (9) | 0.0689 (12) | −0.0083 (10) | 0.0234 (12) | 0.0032 (8) |
| C17 | 0.0840 (16) | 0.0447 (11) | 0.0906 (15) | −0.0277 (11) | 0.0186 (13) | −0.0078 (10) |
| C18 | 0.0573 (11) | 0.0458 (10) | 0.0753 (12) | −0.0151 (8) | 0.0122 (9) | −0.0045 (9) |
| C19 | 0.0456 (9) | 0.0325 (7) | 0.0464 (8) | −0.0056 (6) | 0.0137 (7) | 0.0005 (6) |
| C20 | 0.0472 (9) | 0.0408 (8) | 0.0434 (8) | −0.0030 (7) | 0.0127 (7) | 0.0057 (6) |
| C21 | 0.0621 (11) | 0.0389 (8) | 0.0509 (9) | −0.0035 (7) | 0.0232 (8) | −0.0050 (7) |
| C22 | 0.0640 (12) | 0.0498 (10) | 0.0677 (12) | 0.0024 (9) | 0.0110 (10) | 0.0033 (9) |
| C23 | 0.0871 (16) | 0.0531 (11) | 0.0778 (13) | 0.0152 (11) | 0.0208 (12) | 0.0155 (10) |
| C24 | 0.0629 (13) | 0.0455 (11) | 0.139 (2) | −0.0091 (9) | 0.0271 (15) | 0.0061 (13) |
| C25 | 0.0505 (11) | 0.0415 (10) | 0.1024 (16) | −0.0016 (8) | 0.0153 (10) | 0.0027 (10) |
| S1—C20 | 1.6445 (17) | C8—H8A | 0.9300 |
| F1—C3 | 1.365 (2) | C9—C10 | 1.398 (2) |
| F2—C16 | 1.356 (2) | C10—C11 | 1.412 (2) |
| O1—C20 | 1.3834 (18) | C10—C19 | 1.464 (2) |
| O1—C19 | 1.3868 (19) | C11—C12 | 1.387 (2) |
| O2—C23 | 1.431 (3) | C11—C13 | 1.492 (2) |
| O2—C24 | 1.436 (3) | C12—H12A | 0.9300 |
| O3—C9 | 1.3577 (18) | C13—C14 | 1.378 (3) |
| O3—H1O3 | 0.78 (3) | C13—C18 | 1.386 (2) |
| N1—C19 | 1.283 (2) | C14—C15 | 1.385 (3) |
| N1—N2 | 1.3871 (18) | C14—H14A | 0.9300 |
| N2—C20 | 1.334 (2) | C15—C16 | 1.355 (3) |
| N2—C21 | 1.4749 (19) | C15—H15A | 0.9300 |
| N3—C21 | 1.432 (2) | C16—C17 | 1.353 (3) |
| N3—C22 | 1.448 (3) | C17—C18 | 1.396 (3) |
| N3—C25 | 1.458 (2) | C17—H17A | 0.9300 |
| C1—C2 | 1.386 (2) | C18—H18A | 0.9300 |
| C1—C6 | 1.391 (2) | C21—H21A | 0.9700 |
| C1—H1A | 0.9300 | C21—H21B | 0.9700 |
| C2—C3 | 1.353 (3) | C22—C23 | 1.516 (3) |
| C2—H2A | 0.9300 | C22—H22A | 0.9700 |
| C3—C4 | 1.362 (3) | C22—H22B | 0.9700 |
| C4—C5 | 1.380 (2) | C23—H23A | 0.9700 |
| C4—H4A | 0.9300 | C23—H23B | 0.9700 |
| C5—C6 | 1.392 (2) | C24—C25 | 1.509 (3) |
| C5—H5A | 0.9300 | C24—H24A | 0.9700 |
| C6—C7 | 1.485 (2) | C24—H24B | 0.9700 |
| C7—C12 | 1.395 (2) | C25—H25A | 0.9700 |
| C7—C8 | 1.397 (2) | C25—H25B | 0.9700 |
| C8—C9 | 1.387 (2) | ||
| C20—O1—C19 | 105.32 (12) | C13—C14—H14A | 119.1 |
| C23—O2—C24 | 110.36 (15) | C15—C14—H14A | 119.1 |
| C9—O3—H1O3 | 113.7 (18) | C16—C15—C14 | 118.1 (2) |
| C19—N1—N2 | 103.95 (13) | C16—C15—H15A | 120.9 |
| C20—N2—N1 | 112.27 (12) | C14—C15—H15A | 120.9 |
| C20—N2—C21 | 126.91 (14) | C17—C16—C15 | 122.69 (18) |
| N1—N2—C21 | 120.62 (13) | C17—C16—F2 | 118.7 (2) |
| C21—N3—C22 | 114.98 (15) | C15—C16—F2 | 118.6 (2) |
| C21—N3—C25 | 115.67 (14) | C16—C17—C18 | 119.03 (19) |
| C22—N3—C25 | 111.09 (15) | C16—C17—H17A | 120.5 |
| C2—C1—C6 | 121.44 (18) | C18—C17—H17A | 120.5 |
| C2—C1—H1A | 119.3 | C13—C18—C17 | 120.1 (2) |
| C6—C1—H1A | 119.3 | C13—C18—H18A | 119.9 |
| C3—C2—C1 | 118.32 (18) | C17—C18—H18A | 119.9 |
| C3—C2—H2A | 120.8 | N1—C19—O1 | 113.05 (13) |
| C1—C2—H2A | 120.8 | N1—C19—C10 | 126.79 (15) |
| C2—C3—C4 | 123.01 (17) | O1—C19—C10 | 120.12 (13) |
| C2—C3—F1 | 118.72 (18) | N2—C20—O1 | 105.36 (13) |
| C4—C3—F1 | 118.27 (19) | N2—C20—S1 | 130.84 (12) |
| C3—C4—C5 | 118.36 (19) | O1—C20—S1 | 123.79 (12) |
| C3—C4—H4A | 120.8 | N3—C21—N2 | 115.25 (13) |
| C5—C4—H4A | 120.8 | N3—C21—H21A | 108.5 |
| C4—C5—C6 | 121.45 (17) | N2—C21—H21A | 108.5 |
| C4—C5—H5A | 119.3 | N3—C21—H21B | 108.5 |
| C6—C5—H5A | 119.3 | N2—C21—H21B | 108.5 |
| C1—C6—C5 | 117.43 (15) | H21A—C21—H21B | 107.5 |
| C1—C6—C7 | 121.40 (15) | N3—C22—C23 | 109.02 (18) |
| C5—C6—C7 | 121.14 (15) | N3—C22—H22A | 109.9 |
| C12—C7—C8 | 118.31 (14) | C23—C22—H22A | 109.9 |
| C12—C7—C6 | 120.54 (14) | N3—C22—H22B | 109.9 |
| C8—C7—C6 | 121.07 (14) | C23—C22—H22B | 109.9 |
| C9—C8—C7 | 120.80 (15) | H22A—C22—H22B | 108.3 |
| C9—C8—H8A | 119.6 | O2—C23—C22 | 111.55 (16) |
| C7—C8—H8A | 119.6 | O2—C23—H23A | 109.3 |
| O3—C9—C8 | 122.70 (15) | C22—C23—H23A | 109.3 |
| O3—C9—C10 | 116.67 (14) | O2—C23—H23B | 109.3 |
| C8—C9—C10 | 120.62 (14) | C22—C23—H23B | 109.3 |
| C9—C10—C11 | 119.10 (14) | H23A—C23—H23B | 108.0 |
| C9—C10—C19 | 120.39 (13) | O2—C24—C25 | 110.3 (2) |
| C11—C10—C19 | 120.48 (14) | O2—C24—H24A | 109.6 |
| C12—C11—C10 | 119.26 (14) | C25—C24—H24A | 109.6 |
| C12—C11—C13 | 118.65 (13) | O2—C24—H24B | 109.6 |
| C10—C11—C13 | 121.99 (13) | C25—C24—H24B | 109.6 |
| C11—C12—C7 | 121.89 (14) | H24A—C24—H24B | 108.1 |
| C11—C12—H12A | 119.1 | N3—C25—C24 | 108.40 (16) |
| C7—C12—H12A | 119.1 | N3—C25—H25A | 110.0 |
| C14—C13—C18 | 118.30 (16) | C24—C25—H25A | 110.0 |
| C14—C13—C11 | 120.80 (15) | N3—C25—H25B | 110.0 |
| C18—C13—C11 | 120.83 (17) | C24—C25—H25B | 110.0 |
| C13—C14—C15 | 121.73 (19) | H25A—C25—H25B | 108.4 |
| C19—N1—N2—C20 | 2.31 (17) | C18—C13—C14—C15 | 0.4 (3) |
| C19—N1—N2—C21 | 177.47 (14) | C11—C13—C14—C15 | −176.60 (18) |
| C6—C1—C2—C3 | 0.5 (3) | C13—C14—C15—C16 | −0.6 (3) |
| C1—C2—C3—C4 | −0.2 (3) | C14—C15—C16—C17 | 0.1 (3) |
| C1—C2—C3—F1 | 178.97 (19) | C14—C15—C16—F2 | −179.89 (19) |
| C2—C3—C4—C5 | −0.2 (3) | C15—C16—C17—C18 | 0.7 (3) |
| F1—C3—C4—C5 | −179.36 (19) | F2—C16—C17—C18 | −179.34 (19) |
| C3—C4—C5—C6 | 0.2 (3) | C14—C13—C18—C17 | 0.4 (3) |
| C2—C1—C6—C5 | −0.5 (3) | C11—C13—C18—C17 | 177.39 (17) |
| C2—C1—C6—C7 | −178.59 (18) | C16—C17—C18—C13 | −0.9 (3) |
| C4—C5—C6—C1 | 0.1 (3) | N2—N1—C19—O1 | −1.38 (17) |
| C4—C5—C6—C7 | 178.19 (18) | N2—N1—C19—C10 | 176.19 (14) |
| C1—C6—C7—C12 | −24.7 (3) | C20—O1—C19—N1 | 0.08 (17) |
| C5—C6—C7—C12 | 157.23 (18) | C20—O1—C19—C10 | −177.68 (13) |
| C1—C6—C7—C8 | 152.03 (18) | C9—C10—C19—N1 | 125.76 (19) |
| C5—C6—C7—C8 | −26.0 (3) | C11—C10—C19—N1 | −52.3 (2) |
| C12—C7—C8—C9 | 0.0 (3) | C9—C10—C19—O1 | −56.8 (2) |
| C6—C7—C8—C9 | −176.80 (17) | C11—C10—C19—O1 | 125.07 (16) |
| C7—C8—C9—O3 | 179.61 (18) | N1—N2—C20—O1 | −2.28 (16) |
| C7—C8—C9—C10 | 0.9 (3) | C21—N2—C20—O1 | −177.07 (14) |
| O3—C9—C10—C11 | −179.50 (17) | N1—N2—C20—S1 | 176.89 (12) |
| C8—C9—C10—C11 | −0.8 (3) | C21—N2—C20—S1 | 2.1 (2) |
| O3—C9—C10—C19 | 2.4 (3) | C19—O1—C20—N2 | 1.33 (15) |
| C8—C9—C10—C19 | −178.88 (17) | C19—O1—C20—S1 | −177.92 (12) |
| C9—C10—C11—C12 | −0.4 (3) | C22—N3—C21—N2 | 54.9 (2) |
| C19—C10—C11—C12 | 177.73 (16) | C25—N3—C21—N2 | −76.8 (2) |
| C9—C10—C11—C13 | 175.85 (17) | C20—N2—C21—N3 | −116.90 (18) |
| C19—C10—C11—C13 | −6.0 (3) | N1—N2—C21—N3 | 68.7 (2) |
| C10—C11—C12—C7 | 1.4 (3) | C21—N3—C22—C23 | 168.57 (15) |
| C13—C11—C12—C7 | −174.96 (17) | C25—N3—C22—C23 | −57.65 (19) |
| C8—C7—C12—C11 | −1.2 (3) | C24—O2—C23—C22 | −57.5 (2) |
| C6—C7—C12—C11 | 175.63 (16) | N3—C22—C23—O2 | 56.2 (2) |
| C12—C11—C13—C14 | 116.54 (19) | C23—O2—C24—C25 | 59.3 (2) |
| C10—C11—C13—C14 | −59.7 (2) | C21—N3—C25—C24 | −166.88 (18) |
| C12—C11—C13—C18 | −60.4 (2) | C22—N3—C25—C24 | 59.7 (2) |
| C10—C11—C13—C18 | 123.36 (18) | O2—C24—C25—N3 | −59.7 (2) |
| Cg1 is the centroid of the C7–C12 ring. |
| H··· | ||||
| O3—H1O3···O2i | 0.79 (2) | 1.95 (2) | 2.728 (2) | 167 (2) |
| C5—H5A···S1ii | 0.93 | 2.80 | 3.639 (2) | 151 |
| C12—H12A···F1iii | 0.93 | 2.47 | 3.292 (2) | 148 |
| C23—H23A···F1iv | 0.97 | 2.51 | 3.462 (3) | 167 |
| C1—H1A···Cg1v | 0.93 | 2.91 | 3.414 (2) | 115 |
Hydrogen-bond geometry (Å, °)
Cg1 is the centroid of the C7–C12 ring.
| H⋯ | ||||
|---|---|---|---|---|
| O3—H1 | 0.79 (2) | 1.95 (2) | 2.728 (2) | 167 (2) |
| C5—H5 | 0.93 | 2.80 | 3.639 (2) | 151 |
| C12—H12 | 0.93 | 2.47 | 3.292 (2) | 148 |
| C23—H23 | 0.97 | 2.51 | 3.462 (3) | 167 |
| C1—H1 | 0.93 | 2.91 | 3.414 (2) | 115 |
Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .