| Literature DB >> 22091027 |
Jerry P Jasinski, James A Golen, M S Siddegowda, H S Yathirajan, M T Swamy.
Abstract
In the title compound, C(14)H(13)NO, which has two mol-ecules in the asymmetric unit, the dihedral angles between the mean planes of the benzene rings are 84.6 (7) and 85.0 (6)°. N-H⋯O hydrogen bonds [forming R(2) (2)(8) ring motifs] and C-H⋯O hydrogen bonds dominate the crystal packing, forming zigzag chains parallel to the a axis. In addition, weak inter-molecular C-H⋯π inter-actions are observed.Entities:
Year: 2011 PMID: 22091027 PMCID: PMC3213448 DOI: 10.1107/S1600536811026717
Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN: 1600-5368
| C14H13NO | |
| Monoclinic, | Cu |
| Hall symbol: P 2yb | Cell parameters from 5082 reflections |
| θ = 4.6–70.4° | |
| µ = 0.61 mm−1 | |
| β = 98.152 (5)° | Block, colorless |
| 0.40 × 0.25 × 0.20 mm | |
| Oxford Diffraction Xcalibur Eos Gemini diffractometer | 3978 independent reflections |
| Radiation source: Enhance (Cu) X-ray Source | 3869 reflections with |
| graphite | |
| Detector resolution: 16.1500 pixels mm-1 | θmax = 70.5°, θmin = 5.7° |
| ω scans | |
| Absorption correction: multi-scan ( | |
| 6490 measured reflections |
| Refinement on | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| H atoms treated by a mixture of independent and constrained refinement | |
| (Δ/σ)max = 0.027 | |
| 3978 reflections | Δρmax = 0.21 e Å−3 |
| 303 parameters | Δρmin = −0.20 e Å−3 |
| 9 restraints | Extinction correction: |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0118 (13) |
| Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
| Refinement. Refinement of |
| N1 | 0.9797 (3) | 0.54261 (6) | 0.6365 (2) | 0.0459 (3) | |
| H1B | 1.121 (3) | 0.5307 (8) | 0.600 (3) | 0.055* | |
| H1A | 0.984 (5) | 0.5667 (6) | 0.706 (3) | 0.055* | |
| O2 | 1.0081 (2) | 0.62240 (4) | −0.11977 (17) | 0.0465 (3) | |
| O1 | 0.5496 (2) | 0.53784 (5) | 0.64407 (16) | 0.0459 (3) | |
| N2 | 0.5779 (3) | 0.61736 (6) | −0.1120 (2) | 0.0469 (4) | |
| H2B | 0.561 (5) | 0.5935 (6) | −0.185 (3) | 0.056* | |
| H2A | 0.431 (3) | 0.6281 (9) | −0.080 (3) | 0.056* | |
| C1 | 0.7494 (3) | 0.52226 (5) | 0.5965 (2) | 0.0359 (3) | |
| C2 | 0.7440 (3) | 0.47718 (6) | 0.4902 (2) | 0.0377 (3) | |
| H2C | 0.9097 | 0.4758 | 0.4381 | 0.045* | |
| C3 | 0.5167 (3) | 0.47744 (6) | 0.3416 (2) | 0.0406 (4) | |
| C4 | 0.4550 (5) | 0.51789 (8) | 0.2469 (3) | 0.0678 (6) | |
| H4A | 0.5534 | 0.5456 | 0.2759 | 0.081* | |
| C5 | 0.2520 (6) | 0.51860 (10) | 0.1106 (4) | 0.0824 (8) | |
| H5A | 0.2130 | 0.5467 | 0.0469 | 0.099* | |
| C6 | 0.1062 (5) | 0.47893 (10) | 0.0666 (3) | 0.0683 (6) | |
| H6A | −0.0353 | 0.4796 | −0.0254 | 0.082* | |
| C7 | 0.1684 (4) | 0.43851 (9) | 0.1575 (3) | 0.0577 (5) | |
| H7A | 0.0707 | 0.4108 | 0.1272 | 0.069* | |
| C8 | 0.3724 (4) | 0.43764 (7) | 0.2933 (2) | 0.0461 (4) | |
| H8A | 0.4138 | 0.4092 | 0.3543 | 0.055* | |
| C9 | 0.7419 (3) | 0.43519 (5) | 0.6105 (2) | 0.0375 (3) | |
| C10 | 0.5760 (4) | 0.43225 (7) | 0.7334 (3) | 0.0518 (4) | |
| H10A | 0.4577 | 0.4571 | 0.7451 | 0.062* | |
| C11 | 0.5795 (5) | 0.39352 (9) | 0.8402 (3) | 0.0606 (5) | |
| H11A | 0.4630 | 0.3921 | 0.9239 | 0.073* | |
| C12 | 0.7488 (5) | 0.35715 (8) | 0.8270 (3) | 0.0607 (5) | |
| H12A | 0.7521 | 0.3309 | 0.9020 | 0.073* | |
| C13 | 0.9135 (5) | 0.35925 (9) | 0.7036 (4) | 0.0738 (7) | |
| H13A | 1.0288 | 0.3340 | 0.6910 | 0.089* | |
| C14 | 0.9117 (4) | 0.39807 (8) | 0.5981 (3) | 0.0607 (5) | |
| H14A | 1.0294 | 0.3994 | 0.5151 | 0.073* | |
| C15 | 0.8083 (3) | 0.63780 (6) | −0.0712 (2) | 0.0355 (3) | |
| C16 | 0.8143 (3) | 0.68289 (5) | 0.0360 (2) | 0.0367 (3) | |
| H16A | 0.6495 | 0.6841 | 0.0892 | 0.044* | |
| C17 | 0.8148 (3) | 0.72535 (6) | −0.0840 (2) | 0.0373 (3) | |
| C18 | 0.9825 (4) | 0.72830 (7) | −0.2076 (2) | 0.0505 (4) | |
| H18A | 1.1005 | 0.7034 | −0.2201 | 0.061* | |
| C19 | 0.9779 (4) | 0.76758 (8) | −0.3129 (3) | 0.0594 (5) | |
| H19A | 1.0941 | 0.7694 | −0.3967 | 0.071* | |
| C20 | 0.8089 (5) | 0.80352 (7) | −0.2976 (3) | 0.0585 (5) | |
| H20A | 0.8061 | 0.8301 | −0.3710 | 0.070* | |
| C21 | 0.6427 (5) | 0.80100 (8) | −0.1751 (3) | 0.0654 (6) | |
| H21A | 0.5257 | 0.8260 | −0.1627 | 0.078* | |
| C22 | 0.6461 (4) | 0.76191 (7) | −0.0699 (3) | 0.0533 (5) | |
| H22A | 0.5294 | 0.7603 | 0.0137 | 0.064* | |
| C23 | 1.0422 (3) | 0.68233 (6) | 0.1827 (2) | 0.0404 (3) | |
| C24 | 1.1076 (5) | 0.64165 (8) | 0.2764 (3) | 0.0702 (6) | |
| H24A | 1.0119 | 0.6137 | 0.2462 | 0.084* | |
| C25 | 1.3098 (6) | 0.64110 (11) | 0.4128 (3) | 0.0848 (8) | |
| H25A | 1.3508 | 0.6129 | 0.4757 | 0.102* | |
| C26 | 1.4513 (5) | 0.68078 (11) | 0.4580 (3) | 0.0696 (6) | |
| H26A | 1.5922 | 0.6801 | 0.5505 | 0.084* | |
| C27 | 1.3884 (4) | 0.72136 (9) | 0.3690 (3) | 0.0608 (5) | |
| H27A | 1.4847 | 0.7491 | 0.4008 | 0.073* | |
| C28 | 1.1853 (4) | 0.72226 (7) | 0.2329 (2) | 0.0468 (4) | |
| H28A | 1.1432 | 0.7508 | 0.1727 | 0.056* |
| N1 | 0.0328 (6) | 0.0411 (8) | 0.0651 (9) | −0.0033 (6) | 0.0110 (6) | −0.0140 (7) |
| O2 | 0.0316 (5) | 0.0435 (7) | 0.0654 (7) | −0.0009 (5) | 0.0106 (5) | −0.0159 (5) |
| O1 | 0.0321 (5) | 0.0424 (6) | 0.0639 (7) | −0.0001 (5) | 0.0093 (5) | −0.0150 (6) |
| N2 | 0.0325 (6) | 0.0435 (8) | 0.0652 (9) | −0.0021 (6) | 0.0086 (6) | −0.0147 (7) |
| C1 | 0.0322 (7) | 0.0325 (8) | 0.0430 (8) | 0.0009 (5) | 0.0051 (6) | −0.0007 (6) |
| C2 | 0.0361 (7) | 0.0352 (8) | 0.0436 (8) | −0.0012 (6) | 0.0116 (6) | −0.0032 (7) |
| C3 | 0.0436 (8) | 0.0388 (9) | 0.0407 (8) | −0.0019 (6) | 0.0107 (6) | −0.0039 (7) |
| C4 | 0.0871 (15) | 0.0441 (11) | 0.0663 (13) | −0.0108 (10) | −0.0092 (11) | 0.0077 (9) |
| C5 | 0.107 (2) | 0.0650 (15) | 0.0660 (14) | −0.0016 (14) | −0.0202 (14) | 0.0137 (12) |
| C6 | 0.0713 (13) | 0.0847 (16) | 0.0442 (10) | 0.0011 (12) | −0.0085 (9) | −0.0065 (10) |
| C7 | 0.0624 (11) | 0.0665 (13) | 0.0438 (9) | −0.0133 (10) | 0.0061 (8) | −0.0125 (9) |
| C8 | 0.0545 (9) | 0.0452 (10) | 0.0398 (8) | −0.0061 (8) | 0.0109 (7) | −0.0068 (7) |
| C9 | 0.0368 (7) | 0.0332 (8) | 0.0423 (8) | −0.0013 (6) | 0.0048 (6) | −0.0052 (6) |
| C10 | 0.0547 (10) | 0.0487 (11) | 0.0557 (10) | 0.0113 (8) | 0.0204 (8) | 0.0036 (8) |
| C11 | 0.0734 (13) | 0.0576 (11) | 0.0565 (11) | 0.0015 (10) | 0.0284 (10) | 0.0067 (10) |
| C12 | 0.0769 (13) | 0.0434 (11) | 0.0636 (12) | 0.0004 (10) | 0.0164 (10) | 0.0106 (9) |
| C13 | 0.0837 (15) | 0.0440 (11) | 0.1012 (18) | 0.0193 (11) | 0.0389 (14) | 0.0163 (11) |
| C14 | 0.0657 (12) | 0.0439 (10) | 0.0795 (14) | 0.0133 (9) | 0.0346 (10) | 0.0054 (10) |
| C15 | 0.0327 (7) | 0.0324 (7) | 0.0418 (7) | −0.0002 (6) | 0.0066 (6) | −0.0006 (6) |
| C16 | 0.0357 (7) | 0.0337 (8) | 0.0430 (8) | −0.0020 (6) | 0.0129 (6) | −0.0041 (7) |
| C17 | 0.0363 (7) | 0.0358 (8) | 0.0399 (7) | −0.0021 (6) | 0.0055 (6) | −0.0057 (6) |
| C18 | 0.0531 (10) | 0.0481 (10) | 0.0534 (10) | 0.0080 (8) | 0.0186 (8) | 0.0042 (8) |
| C19 | 0.0686 (12) | 0.0591 (12) | 0.0550 (11) | 0.0016 (10) | 0.0245 (9) | 0.0069 (10) |
| C20 | 0.0752 (13) | 0.0429 (11) | 0.0583 (11) | −0.0010 (9) | 0.0123 (10) | 0.0104 (8) |
| C21 | 0.0786 (15) | 0.0409 (10) | 0.0818 (15) | 0.0171 (9) | 0.0294 (12) | 0.0066 (10) |
| C22 | 0.0597 (10) | 0.0404 (9) | 0.0655 (11) | 0.0073 (8) | 0.0291 (9) | 0.0050 (8) |
| C23 | 0.0451 (8) | 0.0399 (9) | 0.0381 (7) | −0.0005 (6) | 0.0123 (6) | −0.0036 (7) |
| C24 | 0.0878 (16) | 0.0478 (12) | 0.0684 (13) | −0.0088 (11) | −0.0116 (12) | 0.0077 (10) |
| C25 | 0.109 (2) | 0.0685 (16) | 0.0669 (14) | 0.0064 (15) | −0.0228 (14) | 0.0127 (12) |
| C26 | 0.0741 (13) | 0.0856 (16) | 0.0441 (10) | 0.0001 (12) | −0.0091 (9) | −0.0043 (11) |
| C27 | 0.0643 (12) | 0.0720 (14) | 0.0462 (9) | −0.0175 (10) | 0.0081 (9) | −0.0141 (10) |
| C28 | 0.0553 (10) | 0.0452 (10) | 0.0411 (8) | −0.0090 (8) | 0.0112 (7) | −0.0057 (7) |
| N1—C1 | 1.322 (2) | C12—H12A | 0.9500 |
| N1—H1B | 0.889 (13) | C13—C14 | 1.380 (3) |
| N1—H1A | 0.873 (13) | C13—H13A | 0.9500 |
| O2—C15 | 1.2306 (19) | C14—H14A | 0.9500 |
| O1—C1 | 1.2292 (19) | C15—C16 | 1.533 (2) |
| N2—C15 | 1.324 (2) | C16—C23 | 1.521 (2) |
| N2—H2B | 0.883 (13) | C16—C17 | 1.532 (2) |
| N2—H2A | 0.889 (13) | C16—H16A | 1.0000 |
| C1—C2 | 1.529 (2) | C17—C22 | 1.375 (2) |
| C2—C9 | 1.523 (2) | C17—C18 | 1.387 (2) |
| C2—C3 | 1.529 (2) | C18—C19 | 1.388 (3) |
| C2—H2C | 1.0000 | C18—H18A | 0.9500 |
| C3—C8 | 1.382 (2) | C19—C20 | 1.364 (3) |
| C3—C4 | 1.384 (3) | C19—H19A | 0.9500 |
| C4—C5 | 1.384 (3) | C20—C21 | 1.374 (4) |
| C4—H4A | 0.9500 | C20—H20A | 0.9500 |
| C5—C6 | 1.377 (4) | C21—C22 | 1.384 (3) |
| C5—H5A | 0.9500 | C21—H21A | 0.9500 |
| C6—C7 | 1.369 (4) | C22—H22A | 0.9500 |
| C6—H6A | 0.9500 | C23—C28 | 1.385 (2) |
| C7—C8 | 1.385 (3) | C23—C24 | 1.389 (3) |
| C7—H7A | 0.9500 | C24—C25 | 1.382 (3) |
| C8—H8A | 0.9500 | C24—H24A | 0.9500 |
| C9—C10 | 1.377 (3) | C25—C26 | 1.367 (4) |
| C9—C14 | 1.388 (3) | C25—H25A | 0.9500 |
| C10—C11 | 1.383 (3) | C26—C27 | 1.366 (4) |
| C10—H10A | 0.9500 | C26—H26A | 0.9500 |
| C11—C12 | 1.371 (3) | C27—C28 | 1.384 (3) |
| C11—H11A | 0.9500 | C27—H27A | 0.9500 |
| C12—C13 | 1.373 (4) | C28—H28A | 0.9500 |
| C1—N1—H1B | 120.8 (16) | C13—C14—C9 | 121.52 (19) |
| C1—N1—H1A | 115.9 (16) | C13—C14—H14A | 119.2 |
| H1B—N1—H1A | 123 (2) | C9—C14—H14A | 119.2 |
| C15—N2—H2B | 119.8 (16) | O2—C15—N2 | 122.28 (16) |
| C15—N2—H2A | 123.8 (16) | O2—C15—C16 | 120.98 (13) |
| H2B—N2—H2A | 116 (2) | N2—C15—C16 | 116.72 (13) |
| O1—C1—N1 | 122.46 (15) | C23—C16—C17 | 113.57 (13) |
| O1—C1—C2 | 121.11 (14) | C23—C16—C15 | 110.82 (13) |
| N1—C1—C2 | 116.42 (14) | C17—C16—C15 | 109.44 (12) |
| C9—C2—C1 | 109.27 (13) | C23—C16—H16A | 107.6 |
| C9—C2—C3 | 113.52 (13) | C17—C16—H16A | 107.6 |
| C1—C2—C3 | 111.11 (13) | C15—C16—H16A | 107.6 |
| C9—C2—H2C | 107.6 | C22—C17—C18 | 118.40 (16) |
| C1—C2—H2C | 107.6 | C22—C17—C16 | 119.72 (14) |
| C3—C2—H2C | 107.6 | C18—C17—C16 | 121.88 (14) |
| C8—C3—C4 | 117.79 (17) | C17—C18—C19 | 120.03 (18) |
| C8—C3—C2 | 121.97 (15) | C17—C18—H18A | 120.0 |
| C4—C3—C2 | 120.21 (16) | C19—C18—H18A | 120.0 |
| C5—C4—C3 | 121.0 (2) | C20—C19—C18 | 120.89 (19) |
| C5—C4—H4A | 119.5 | C20—C19—H19A | 119.6 |
| C3—C4—H4A | 119.5 | C18—C19—H19A | 119.6 |
| C4—C5—C6 | 120.5 (2) | C19—C20—C21 | 119.51 (19) |
| C4—C5—H5A | 119.7 | C19—C20—H20A | 120.2 |
| C6—C5—H5A | 119.7 | C21—C20—H20A | 120.2 |
| C7—C6—C5 | 119.0 (2) | C20—C21—C22 | 119.9 (2) |
| C7—C6—H6A | 120.5 | C20—C21—H21A | 120.1 |
| C5—C6—H6A | 120.5 | C22—C21—H21A | 120.1 |
| C6—C7—C8 | 120.59 (19) | C17—C22—C21 | 121.31 (19) |
| C6—C7—H7A | 119.7 | C17—C22—H22A | 119.3 |
| C8—C7—H7A | 119.7 | C21—C22—H22A | 119.3 |
| C3—C8—C7 | 121.11 (18) | C28—C23—C24 | 117.35 (17) |
| C3—C8—H8A | 119.4 | C28—C23—C16 | 121.97 (15) |
| C7—C8—H8A | 119.4 | C24—C23—C16 | 120.64 (16) |
| C10—C9—C14 | 117.65 (17) | C25—C24—C23 | 121.1 (2) |
| C10—C9—C2 | 122.44 (15) | C25—C24—H24A | 119.5 |
| C14—C9—C2 | 119.91 (15) | C23—C24—H24A | 119.5 |
| C9—C10—C11 | 120.79 (18) | C26—C25—C24 | 120.5 (2) |
| C9—C10—H10A | 119.6 | C26—C25—H25A | 119.7 |
| C11—C10—H10A | 119.6 | C24—C25—H25A | 119.7 |
| C12—C11—C10 | 120.97 (19) | C25—C26—C27 | 119.4 (2) |
| C12—C11—H11A | 119.5 | C25—C26—H26A | 120.3 |
| C10—C11—H11A | 119.5 | C27—C26—H26A | 120.3 |
| C11—C12—C13 | 119.0 (2) | C26—C27—C28 | 120.4 (2) |
| C11—C12—H12A | 120.5 | C26—C27—H27A | 119.8 |
| C13—C12—H12A | 120.5 | C28—C27—H27A | 119.8 |
| C12—C13—C14 | 120.0 (2) | C27—C28—C23 | 121.22 (18) |
| C12—C13—H13A | 120.0 | C27—C28—H28A | 119.4 |
| C14—C13—H13A | 120.0 | C23—C28—H28A | 119.4 |
| O1—C1—C2—C9 | −79.23 (19) | O2—C15—C16—C23 | −46.8 (2) |
| N1—C1—C2—C9 | 99.42 (17) | N2—C15—C16—C23 | 135.00 (15) |
| O1—C1—C2—C3 | 46.8 (2) | O2—C15—C16—C17 | 79.24 (18) |
| N1—C1—C2—C3 | −134.55 (16) | N2—C15—C16—C17 | −99.00 (16) |
| C9—C2—C3—C8 | −17.6 (2) | C23—C16—C17—C22 | −103.20 (18) |
| C1—C2—C3—C8 | −141.21 (16) | C15—C16—C17—C22 | 132.39 (17) |
| C9—C2—C3—C4 | 164.54 (19) | C23—C16—C17—C18 | 76.54 (19) |
| C1—C2—C3—C4 | 40.9 (2) | C15—C16—C17—C18 | −47.87 (19) |
| C8—C3—C4—C5 | 1.2 (4) | C22—C17—C18—C19 | 0.2 (3) |
| C2—C3—C4—C5 | 179.2 (2) | C16—C17—C18—C19 | −179.50 (18) |
| C3—C4—C5—C6 | 0.2 (5) | C17—C18—C19—C20 | −0.4 (3) |
| C4—C5—C6—C7 | −1.3 (5) | C18—C19—C20—C21 | 0.6 (4) |
| C5—C6—C7—C8 | 0.9 (4) | C19—C20—C21—C22 | −0.7 (4) |
| C4—C3—C8—C7 | −1.6 (3) | C18—C17—C22—C21 | −0.3 (3) |
| C2—C3—C8—C7 | −179.55 (17) | C16—C17—C22—C21 | 179.4 (2) |
| C6—C7—C8—C3 | 0.6 (3) | C20—C21—C22—C17 | 0.6 (4) |
| C1—C2—C9—C10 | 47.5 (2) | C17—C16—C23—C28 | 18.5 (2) |
| C3—C2—C9—C10 | −77.1 (2) | C15—C16—C23—C28 | 142.15 (16) |
| C1—C2—C9—C14 | −132.47 (18) | C17—C16—C23—C24 | −164.12 (19) |
| C3—C2—C9—C14 | 102.9 (2) | C15—C16—C23—C24 | −40.5 (2) |
| C14—C9—C10—C11 | −0.1 (3) | C28—C23—C24—C25 | −0.8 (4) |
| C2—C9—C10—C11 | 179.91 (18) | C16—C23—C24—C25 | −178.3 (2) |
| C9—C10—C11—C12 | 0.3 (3) | C23—C24—C25—C26 | −0.4 (5) |
| C10—C11—C12—C13 | −1.0 (4) | C24—C25—C26—C27 | 1.1 (5) |
| C11—C12—C13—C14 | 1.6 (4) | C25—C26—C27—C28 | −0.8 (4) |
| C12—C13—C14—C9 | −1.4 (4) | C26—C27—C28—C23 | −0.4 (3) |
| C10—C9—C14—C13 | 0.7 (3) | C24—C23—C28—C27 | 1.1 (3) |
| C2—C9—C14—C13 | −179.3 (2) | C16—C23—C28—C27 | 178.60 (17) |
| Cg1 and Cg4 are the centroids of the C3–C8 and C23–C28 rings, respectively. |
| H··· | ||||
| N1—H1B···O1i | 0.89 (1) | 2.20 (2) | 2.9409 (17) | 140 (2) |
| N1—H1A···O2ii | 0.87 (1) | 2.09 (1) | 2.9575 (19) | 177 (2) |
| N2—H2B···O1iii | 0.88 (1) | 2.07 (1) | 2.9526 (19) | 176 (2) |
| N2—H2A···O2iv | 0.89 (1) | 2.17 (2) | 2.9407 (18) | 145 (2) |
| N1—H1A···N2ii | 0.87 (1) | 3.06 (2) | 3.7246 (18) | 134.(2) |
| N2—H2B···N1iii | 0.88 (1) | 3.10 (2) | 3.7246 (18) | 130.(2) |
| C10—H10A···O1 | 0.95 | 2.50 | 3.093 (2) | 120. |
| C18—H18A···O2 | 0.95 | 2.51 | 3.099 (2) | 120 |
| C2—H2C···Cg1i | 1.00 | 2.96 | 3.9379 (18) | 165 |
| C16—H16A···Cg4iv | 1.00 | 2.95 | 3.9263 (18) | 166 |
Hydrogen-bond geometry (Å, °)
Cg1 and Cg4 are the centroids of the C3–C8 and C23–C28 rings, respectively.
| H⋯ | ||||
|---|---|---|---|---|
| N1—H1 | 0.89 (1) | 2.20 (2) | 2.9409 (17) | 140 (2) |
| N1—H1 | 0.87 (1) | 2.09 (1) | 2.9575 (19) | 177 (2) |
| N2—H2 | 0.88 (1) | 2.07 (1) | 2.9526 (19) | 176 (2) |
| N2—H2 | 0.89 (1) | 2.17 (2) | 2.9407 (18) | 145 (2) |
| N1—H1 | 0.87 (1) | 3.06 (2) | 3.7246 (18) | 134 (2) |
| N2—H2 | 0.88 (1) | 3.10 (2) | 3.7246 (18) | 130 (2) |
| C10—H10 | 0.95 | 2.50 | 3.093 (2) | 120 |
| C18—H18 | 0.95 | 2.51 | 3.099 (2) | 120 |
| C2—H2 | 1.00 | 2.96 | 3.9379 (18) | 165 |
| C16—H16 | 1.00 | 2.95 | 3.9263 (18) | 166 |
Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .