| Literature DB >> 24454252 |
P B Sreeja1, M Sithambaresan2, N Aiswarya3, M R Prathapachandra Kurup3.
Abstract
The asymmetric unit of the title compound, C14H11FN2O, contains two independent mol-ecules, both of which adopt the E conformation with respect to the azomethine C=N bond. The mol-ecules are non-planar, with dihedral angles of 26.92 (12) and 11.36 (11)° between the benzene and phenyl rings. In the crystal, mol-ecules are linked through N-H⋯O=C and N-H⋯N hydrogen bonds into chains along [101]. C-H⋯O contacts link these chains into layers parallel to (001). The three-dimensional crystal packing is stabilized by π-π inter-actions, the shortest separation between the centroids of benzene rings being 3.884 (1) Å.Entities:
Year: 2013 PMID: 24454252 PMCID: PMC3885076 DOI: 10.1107/S1600536813031747
Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN: 1600-5368
| C14H11FN2O | |
| Monoclinic, | Mo |
| Hall symbol: -P 2yn | Cell parameters from 4473 reflections |
| θ = 4.7–48.2° | |
| µ = 0.10 mm−1 | |
| β = 104.126 (4)° | Block, colourless |
| 0.35 × 0.30 × 0.25 mm | |
| Bruker Kappa APEXII CCD area-detector diffractometer | 6111 independent reflections |
| Radiation source: fine-focus sealed tube | 3320 reflections with |
| Graphite monochromator | |
| Detector resolution: 8.33 pixels mm-1 | θmax = 28.3°, θmin = 2.5° |
| ω and φ scan | |
| Absorption correction: multi-scan ( | |
| 18766 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 | |
| 5972 reflections | (Δ/σ)max = 0.001 |
| 333 parameters | Δρmax = 0.21 e Å−3 |
| 2 restraints | Δρmin = −0.17 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 |
| F1 | 0.46744 (16) | 0.52151 (9) | 0.31008 (10) | 0.0961 (5) | |
| F2 | 0.04425 (16) | 0.24110 (10) | 0.23115 (9) | 0.0973 (5) | |
| O1 | 0.42500 (14) | 0.14776 (8) | 0.21005 (9) | 0.0613 (4) | |
| O2 | 0.28675 (14) | 0.15829 (9) | −0.13577 (9) | 0.0630 (4) | |
| N1 | 0.44609 (15) | 0.29885 (10) | 0.23441 (10) | 0.0513 (4) | |
| N2 | 0.54248 (16) | 0.24863 (9) | 0.28584 (10) | 0.0505 (4) | |
| N3 | 0.16870 (15) | 0.19149 (9) | 0.00186 (10) | 0.0490 (4) | |
| N4 | 0.30586 (16) | 0.16402 (10) | 0.01524 (11) | 0.0512 (4) | |
| C1 | 0.3744 (2) | 0.50230 (12) | 0.23098 (15) | 0.0591 (5) | |
| C2 | 0.2916 (3) | 0.55868 (13) | 0.18222 (19) | 0.0736 (6) | |
| H2 | 0.3001 | 0.6092 | 0.2028 | 0.088* | |
| C3 | 0.1957 (3) | 0.53942 (15) | 0.1024 (2) | 0.0862 (8) | |
| H3 | 0.1382 | 0.5770 | 0.0680 | 0.103* | |
| C4 | 0.1845 (3) | 0.46473 (16) | 0.07311 (19) | 0.0900 (8) | |
| H4 | 0.1194 | 0.4517 | 0.0187 | 0.108* | |
| C5 | 0.2685 (2) | 0.40901 (13) | 0.12344 (15) | 0.0706 (6) | |
| H5 | 0.2595 | 0.3585 | 0.1026 | 0.085* | |
| C6 | 0.36690 (19) | 0.42641 (11) | 0.20489 (13) | 0.0506 (5) | |
| C7 | 0.46029 (19) | 0.36878 (12) | 0.25810 (13) | 0.0539 (5) | |
| H7 | 0.5304 | 0.3832 | 0.3095 | 0.065* | |
| C8 | 0.52872 (18) | 0.17362 (11) | 0.26640 (11) | 0.0464 (4) | |
| C9 | 0.64558 (19) | 0.12175 (11) | 0.31359 (12) | 0.0490 (4) | |
| C10 | 0.6233 (3) | 0.04460 (14) | 0.30166 (17) | 0.0771 (7) | |
| H10 | 0.5351 | 0.0268 | 0.2689 | 0.093* | |
| C11 | 0.7297 (3) | −0.00725 (16) | 0.33747 (19) | 0.0953 (9) | |
| H11 | 0.7136 | −0.0596 | 0.3280 | 0.114* | |
| C12 | 0.8586 (3) | 0.01828 (16) | 0.38681 (18) | 0.0840 (8) | |
| H12 | 0.9303 | −0.0166 | 0.4118 | 0.101* | |
| C13 | 0.8819 (2) | 0.09439 (17) | 0.39922 (19) | 0.0865 (8) | |
| H13 | 0.9699 | 0.1119 | 0.4327 | 0.104* | |
| C14 | 0.7759 (2) | 0.14642 (14) | 0.36265 (16) | 0.0711 (6) | |
| H14 | 0.7932 | 0.1988 | 0.3714 | 0.085* | |
| C15 | −0.0531 (2) | 0.24951 (13) | 0.15067 (14) | 0.0599 (5) | |
| C16 | −0.1862 (3) | 0.27441 (13) | 0.15287 (17) | 0.0698 (6) | |
| H16 | −0.2083 | 0.2854 | 0.2084 | 0.084* | |
| C17 | −0.2853 (2) | 0.28265 (13) | 0.07180 (19) | 0.0710 (6) | |
| H17 | −0.3766 | 0.2990 | 0.0718 | 0.085* | |
| C18 | −0.2513 (2) | 0.26703 (13) | −0.00981 (16) | 0.0674 (6) | |
| H18 | −0.3194 | 0.2730 | −0.0650 | 0.081* | |
| C19 | −0.1169 (2) | 0.24265 (12) | −0.01023 (14) | 0.0565 (5) | |
| H19 | −0.0948 | 0.2323 | −0.0660 | 0.068* | |
| C20 | −0.01365 (19) | 0.23326 (10) | 0.07091 (13) | 0.0488 (4) | |
| C21 | 0.1288 (2) | 0.20552 (11) | 0.07427 (13) | 0.0514 (5) | |
| H21 | 0.1920 | 0.1979 | 0.1311 | 0.062* | |
| C22 | 0.35624 (18) | 0.14576 (10) | −0.05743 (12) | 0.0461 (4) | |
| C23 | 0.49959 (18) | 0.11042 (10) | −0.03891 (12) | 0.0476 (4) | |
| C24 | 0.5548 (2) | 0.09675 (15) | −0.11316 (16) | 0.0715 (6) | |
| H24 | 0.5039 | 0.1104 | −0.1719 | 0.086* | |
| C25 | 0.6874 (3) | 0.06241 (17) | −0.1000 (2) | 0.0918 (8) | |
| H25 | 0.7244 | 0.0524 | −0.1505 | 0.110* | |
| C26 | 0.7637 (3) | 0.04326 (15) | −0.0146 (2) | 0.0873 (8) | |
| H26 | 0.8531 | 0.0210 | −0.0067 | 0.105* | |
| C27 | 0.7102 (2) | 0.05644 (14) | 0.05883 (18) | 0.0747 (7) | |
| H27 | 0.7626 | 0.0433 | 0.1174 | 0.090* | |
| C28 | 0.5777 (2) | 0.08945 (12) | 0.04711 (14) | 0.0604 (5) | |
| H28 | 0.5406 | 0.0976 | 0.0979 | 0.073* | |
| H4' | 0.3472 (19) | 0.1550 (11) | 0.0722 (7) | 0.060 (6)* | |
| H2' | 0.6116 (18) | 0.2682 (12) | 0.3300 (12) | 0.077 (7)* |
| F1 | 0.0962 (10) | 0.0799 (10) | 0.0961 (10) | −0.0050 (8) | −0.0077 (9) | −0.0251 (8) |
| F2 | 0.0970 (10) | 0.1417 (14) | 0.0495 (7) | 0.0320 (9) | 0.0106 (7) | −0.0092 (8) |
| O1 | 0.0577 (8) | 0.0644 (9) | 0.0510 (7) | −0.0008 (6) | −0.0076 (6) | −0.0029 (6) |
| O2 | 0.0597 (8) | 0.0844 (11) | 0.0418 (7) | 0.0165 (7) | 0.0064 (6) | 0.0050 (7) |
| N1 | 0.0475 (9) | 0.0575 (11) | 0.0449 (8) | 0.0057 (7) | 0.0036 (7) | 0.0017 (7) |
| N2 | 0.0483 (9) | 0.0535 (10) | 0.0430 (8) | 0.0049 (7) | −0.0015 (7) | −0.0018 (7) |
| N3 | 0.0430 (8) | 0.0565 (10) | 0.0446 (8) | 0.0079 (7) | 0.0054 (7) | −0.0006 (7) |
| N4 | 0.0448 (8) | 0.0657 (11) | 0.0392 (8) | 0.0139 (7) | 0.0027 (7) | 0.0006 (8) |
| C1 | 0.0513 (11) | 0.0597 (14) | 0.0664 (13) | −0.0037 (9) | 0.0146 (10) | −0.0060 (11) |
| C2 | 0.0728 (15) | 0.0510 (13) | 0.1003 (18) | 0.0042 (11) | 0.0276 (14) | 0.0002 (12) |
| C3 | 0.0769 (16) | 0.0693 (17) | 0.102 (2) | 0.0155 (13) | 0.0025 (15) | 0.0153 (15) |
| C4 | 0.0893 (18) | 0.0762 (18) | 0.0841 (17) | 0.0092 (14) | −0.0184 (14) | 0.0068 (14) |
| C5 | 0.0721 (14) | 0.0571 (14) | 0.0712 (14) | 0.0045 (11) | −0.0045 (12) | 0.0013 (11) |
| C6 | 0.0443 (10) | 0.0538 (12) | 0.0536 (11) | 0.0000 (8) | 0.0120 (8) | 0.0014 (9) |
| C7 | 0.0508 (11) | 0.0570 (13) | 0.0499 (11) | 0.0003 (9) | 0.0047 (8) | −0.0034 (9) |
| C8 | 0.0449 (10) | 0.0579 (12) | 0.0339 (9) | 0.0026 (8) | 0.0049 (7) | −0.0002 (8) |
| C9 | 0.0527 (11) | 0.0529 (12) | 0.0392 (9) | 0.0048 (8) | 0.0066 (8) | 0.0013 (8) |
| C10 | 0.0804 (16) | 0.0602 (15) | 0.0766 (15) | 0.0064 (11) | −0.0081 (13) | −0.0036 (12) |
| C11 | 0.115 (2) | 0.0582 (16) | 0.097 (2) | 0.0206 (14) | −0.0042 (17) | 0.0005 (14) |
| C12 | 0.0837 (18) | 0.0819 (19) | 0.0815 (17) | 0.0333 (14) | 0.0107 (14) | 0.0127 (14) |
| C13 | 0.0576 (13) | 0.091 (2) | 0.0985 (19) | 0.0129 (13) | −0.0052 (13) | 0.0154 (16) |
| C14 | 0.0556 (12) | 0.0655 (15) | 0.0806 (15) | 0.0029 (10) | −0.0058 (11) | 0.0068 (12) |
| C15 | 0.0647 (13) | 0.0636 (13) | 0.0505 (11) | 0.0088 (10) | 0.0124 (10) | −0.0022 (10) |
| C16 | 0.0799 (16) | 0.0693 (15) | 0.0690 (14) | 0.0092 (12) | 0.0351 (13) | −0.0027 (11) |
| C17 | 0.0558 (13) | 0.0658 (15) | 0.0957 (18) | 0.0097 (10) | 0.0266 (13) | 0.0038 (13) |
| C18 | 0.0555 (12) | 0.0709 (15) | 0.0712 (14) | 0.0073 (10) | 0.0064 (11) | 0.0061 (12) |
| C19 | 0.0539 (11) | 0.0628 (13) | 0.0524 (11) | 0.0068 (9) | 0.0123 (9) | 0.0023 (10) |
| C20 | 0.0527 (11) | 0.0445 (11) | 0.0491 (10) | 0.0036 (8) | 0.0121 (9) | −0.0005 (8) |
| C21 | 0.0500 (10) | 0.0604 (12) | 0.0407 (10) | 0.0085 (9) | 0.0052 (8) | 0.0004 (9) |
| C22 | 0.0465 (10) | 0.0460 (11) | 0.0436 (10) | 0.0009 (8) | 0.0070 (8) | 0.0003 (8) |
| C23 | 0.0442 (10) | 0.0446 (11) | 0.0535 (11) | −0.0015 (8) | 0.0108 (8) | −0.0041 (8) |
| C24 | 0.0652 (14) | 0.0886 (18) | 0.0640 (13) | 0.0070 (12) | 0.0222 (11) | −0.0062 (12) |
| C25 | 0.0751 (17) | 0.112 (2) | 0.101 (2) | 0.0148 (15) | 0.0460 (16) | −0.0117 (17) |
| C26 | 0.0539 (14) | 0.0893 (19) | 0.121 (2) | 0.0176 (12) | 0.0263 (15) | 0.0003 (17) |
| C27 | 0.0528 (12) | 0.0787 (16) | 0.0863 (17) | 0.0179 (11) | 0.0046 (12) | 0.0043 (13) |
| C28 | 0.0532 (11) | 0.0659 (14) | 0.0599 (12) | 0.0128 (10) | 0.0091 (10) | 0.0017 (10) |
| F1—C1 | 1.346 (2) | C11—H11 | 0.9300 |
| F2—C15 | 1.347 (2) | C12—C13 | 1.350 (4) |
| O1—C8 | 1.231 (2) | C12—H12 | 0.9300 |
| O2—C22 | 1.223 (2) | C13—C14 | 1.380 (3) |
| N1—C7 | 1.266 (2) | C13—H13 | 0.9300 |
| N1—N2 | 1.372 (2) | C14—H14 | 0.9300 |
| N2—C8 | 1.338 (2) | C15—C16 | 1.370 (3) |
| N2—H2' | 0.887 (9) | C15—C20 | 1.372 (3) |
| N3—C21 | 1.263 (2) | C16—C17 | 1.362 (3) |
| N3—N4 | 1.382 (2) | C16—H16 | 0.9300 |
| N4—C22 | 1.337 (2) | C17—C18 | 1.371 (3) |
| N4—H4' | 0.865 (9) | C17—H17 | 0.9300 |
| C1—C2 | 1.363 (3) | C18—C19 | 1.373 (3) |
| C1—C6 | 1.375 (3) | C18—H18 | 0.9300 |
| C2—C3 | 1.367 (4) | C19—C20 | 1.384 (3) |
| C2—H2 | 0.9300 | C19—H19 | 0.9300 |
| C3—C4 | 1.368 (4) | C20—C21 | 1.453 (3) |
| C3—H3 | 0.9300 | C21—H21 | 0.9300 |
| C4—C5 | 1.370 (3) | C22—C23 | 1.484 (2) |
| C4—H4 | 0.9300 | C23—C24 | 1.370 (3) |
| C5—C6 | 1.388 (3) | C23—C28 | 1.377 (3) |
| C5—H5 | 0.9300 | C24—C25 | 1.388 (3) |
| C6—C7 | 1.453 (3) | C24—H24 | 0.9300 |
| C7—H7 | 0.9300 | C25—C26 | 1.356 (4) |
| C8—C9 | 1.487 (2) | C25—H25 | 0.9300 |
| C9—C10 | 1.365 (3) | C26—C27 | 1.347 (4) |
| C9—C14 | 1.368 (3) | C26—H26 | 0.9300 |
| C10—C11 | 1.378 (3) | C27—C28 | 1.380 (3) |
| C10—H10 | 0.9300 | C27—H27 | 0.9300 |
| C11—C12 | 1.363 (4) | C28—H28 | 0.9300 |
| C7—N1—N2 | 116.26 (15) | C14—C13—H13 | 119.8 |
| C8—N2—N1 | 118.79 (15) | C9—C14—C13 | 120.6 (2) |
| C8—N2—H2' | 123.7 (15) | C9—C14—H14 | 119.7 |
| N1—N2—H2' | 117.5 (15) | C13—C14—H14 | 119.7 |
| C21—N3—N4 | 115.38 (15) | F2—C15—C16 | 118.13 (19) |
| C22—N4—N3 | 119.63 (14) | F2—C15—C20 | 118.40 (18) |
| C22—N4—H4' | 126.0 (13) | C16—C15—C20 | 123.5 (2) |
| N3—N4—H4' | 113.9 (13) | C17—C16—C15 | 118.4 (2) |
| F1—C1—C2 | 118.3 (2) | C17—C16—H16 | 120.8 |
| F1—C1—C6 | 117.84 (19) | C15—C16—H16 | 120.8 |
| C2—C1—C6 | 123.8 (2) | C16—C17—C18 | 120.3 (2) |
| C1—C2—C3 | 118.7 (2) | C16—C17—H17 | 119.8 |
| C1—C2—H2 | 120.7 | C18—C17—H17 | 119.8 |
| C3—C2—H2 | 120.7 | C17—C18—C19 | 120.1 (2) |
| C2—C3—C4 | 119.9 (2) | C17—C18—H18 | 119.9 |
| C2—C3—H3 | 120.1 | C19—C18—H18 | 119.9 |
| C4—C3—H3 | 120.1 | C18—C19—C20 | 121.1 (2) |
| C3—C4—C5 | 120.4 (2) | C18—C19—H19 | 119.4 |
| C3—C4—H4 | 119.8 | C20—C19—H19 | 119.4 |
| C5—C4—H4 | 119.8 | C15—C20—C19 | 116.53 (18) |
| C4—C5—C6 | 121.3 (2) | C15—C20—C21 | 120.25 (17) |
| C4—C5—H5 | 119.4 | C19—C20—C21 | 123.20 (18) |
| C6—C5—H5 | 119.4 | N3—C21—C20 | 121.54 (16) |
| C1—C6—C5 | 115.95 (18) | N3—C21—H21 | 119.2 |
| C1—C6—C7 | 121.65 (18) | C20—C21—H21 | 119.2 |
| C5—C6—C7 | 122.37 (19) | O2—C22—N4 | 121.02 (16) |
| N1—C7—C6 | 119.94 (17) | O2—C22—C23 | 121.70 (17) |
| N1—C7—H7 | 120.0 | N4—C22—C23 | 117.27 (15) |
| C6—C7—H7 | 120.0 | C24—C23—C28 | 118.78 (18) |
| O1—C8—N2 | 121.89 (16) | C24—C23—C22 | 117.03 (17) |
| O1—C8—C9 | 120.36 (18) | C28—C23—C22 | 124.17 (18) |
| N2—C8—C9 | 117.73 (15) | C23—C24—C25 | 119.5 (2) |
| C10—C9—C14 | 118.38 (19) | C23—C24—H24 | 120.3 |
| C10—C9—C8 | 117.23 (18) | C25—C24—H24 | 120.3 |
| C14—C9—C8 | 124.25 (19) | C26—C25—C24 | 120.9 (3) |
| C9—C10—C11 | 120.9 (2) | C26—C25—H25 | 119.6 |
| C9—C10—H10 | 119.5 | C24—C25—H25 | 119.6 |
| C11—C10—H10 | 119.5 | C27—C26—C25 | 120.0 (2) |
| C12—C11—C10 | 119.9 (3) | C27—C26—H26 | 120.0 |
| C12—C11—H11 | 120.0 | C25—C26—H26 | 120.0 |
| C10—C11—H11 | 120.0 | C26—C27—C28 | 120.0 (2) |
| C13—C12—C11 | 119.7 (2) | C26—C27—H27 | 120.0 |
| C13—C12—H12 | 120.2 | C28—C27—H27 | 120.0 |
| C11—C12—H12 | 120.2 | C23—C28—C27 | 120.8 (2) |
| C12—C13—C14 | 120.5 (2) | C23—C28—H28 | 119.6 |
| C12—C13—H13 | 119.8 | C27—C28—H28 | 119.6 |
| C7—N1—N2—C8 | 177.11 (17) | C12—C13—C14—C9 | 0.3 (4) |
| C21—N3—N4—C22 | 178.37 (18) | F2—C15—C16—C17 | −179.7 (2) |
| F1—C1—C2—C3 | −179.3 (2) | C20—C15—C16—C17 | 0.8 (4) |
| C6—C1—C2—C3 | −0.3 (4) | C15—C16—C17—C18 | −0.7 (4) |
| C1—C2—C3—C4 | 0.0 (4) | C16—C17—C18—C19 | 0.3 (4) |
| C2—C3—C4—C5 | 0.2 (5) | C17—C18—C19—C20 | 0.1 (3) |
| C3—C4—C5—C6 | −0.1 (4) | F2—C15—C20—C19 | 179.99 (19) |
| F1—C1—C6—C5 | 179.36 (19) | C16—C15—C20—C19 | −0.5 (3) |
| C2—C1—C6—C5 | 0.4 (3) | F2—C15—C20—C21 | 1.8 (3) |
| F1—C1—C6—C7 | −2.7 (3) | C16—C15—C20—C21 | −178.7 (2) |
| C2—C1—C6—C7 | 178.3 (2) | C18—C19—C20—C15 | 0.0 (3) |
| C4—C5—C6—C1 | −0.2 (3) | C18—C19—C20—C21 | 178.2 (2) |
| C4—C5—C6—C7 | −178.1 (2) | N4—N3—C21—C20 | −178.78 (17) |
| N2—N1—C7—C6 | 177.19 (16) | C15—C20—C21—N3 | −178.67 (19) |
| C1—C6—C7—N1 | 176.73 (19) | C19—C20—C21—N3 | 3.3 (3) |
| C5—C6—C7—N1 | −5.5 (3) | N3—N4—C22—O2 | 5.5 (3) |
| N1—N2—C8—O1 | −7.2 (3) | N3—N4—C22—C23 | −174.97 (16) |
| N1—N2—C8—C9 | 171.27 (15) | O2—C22—C23—C24 | 4.0 (3) |
| O1—C8—C9—C10 | −9.0 (3) | N4—C22—C23—C24 | −175.59 (18) |
| N2—C8—C9—C10 | 172.51 (19) | O2—C22—C23—C28 | −174.60 (19) |
| O1—C8—C9—C14 | 166.5 (2) | N4—C22—C23—C28 | 5.8 (3) |
| N2—C8—C9—C14 | −12.0 (3) | C28—C23—C24—C25 | −0.1 (3) |
| C14—C9—C10—C11 | −0.5 (4) | C22—C23—C24—C25 | −178.8 (2) |
| C8—C9—C10—C11 | 175.3 (2) | C23—C24—C25—C26 | −0.9 (4) |
| C9—C10—C11—C12 | 1.0 (4) | C24—C25—C26—C27 | 1.0 (4) |
| C10—C11—C12—C13 | −0.9 (4) | C25—C26—C27—C28 | 0.0 (4) |
| C11—C12—C13—C14 | 0.3 (4) | C24—C23—C28—C27 | 1.1 (3) |
| C10—C9—C14—C13 | −0.1 (4) | C22—C23—C28—C27 | 179.6 (2) |
| C8—C9—C14—C13 | −175.6 (2) | C26—C27—C28—C23 | −1.0 (4) |
| H··· | ||||
| N2—H2′···O2i | 0.89 (1) | 2.09 (2) | 2.875 (2) | 147 (2) |
| N2—H2′···N3i | 0.89 (1) | 2.60 (2) | 3.339 (2) | 142 (2) |
| N4—H4′···O1 | 0.87 (1) | 2.03 (1) | 2.882 (2) | 171 (2) |
| C7—H7···O2i | 0.93 | 2.53 | 3.213 (2) | 131 |
| C14—H14···O2i | 0.93 | 2.49 | 3.402 (3) | 166 |
| C16—H16···O2ii | 0.93 | 2.55 | 3.450 (3) | 164 |
| C21—H21···O1 | 0.93 | 2.44 | 3.250 (2) | 145 |
| C28—H28···O1 | 0.93 | 2.40 | 3.312 (2) | 166 |
Hydrogen-bond geometry (Å, °)
|
|
| H⋯ |
|
|
|---|---|---|---|---|
| N2—H2′⋯O2i | 0.89 (1) | 2.09 (2) | 2.875 (2) | 147 (2) |
| N2—H2′⋯N3i | 0.89 (1) | 2.60 (2) | 3.339 (2) | 142 (2) |
| N4—H4′⋯O1 | 0.87 (1) | 2.03 (1) | 2.882 (2) | 171 (2) |
| C7—H7⋯O2i | 0.93 | 2.53 | 3.213 (2) | 131 |
| C14—H14⋯O2i | 0.93 | 2.49 | 3.402 (3) | 166 |
| C16—H16⋯O2ii | 0.93 | 2.55 | 3.450 (3) | 164 |
| C21—H21⋯O1 | 0.93 | 2.44 | 3.250 (2) | 145 |
| C28—H28⋯O1 | 0.93 | 2.40 | 3.312 (2) | 166 |
Symmetry codes: (i) ; (ii) .