| Literature DB >> 22219945 |
Chunli Wu1, Wei Lei, Huiyan Ma, Jiabin Qiao, Aixing Li.
Abstract
The asymmetric unit of the title compound, C(12)H(9)F(2)N(3)O, contains two independent mol-ecules (A and B) in which the benzene and cyclo-propane rings form dihedral angles of 33.0 (1) and 29.7 (1)°, respectively. In the crystal, weak inter-molecular C-H⋯O hydrogen bonds link alternating A and B mol-ecules into chains along [010].Entities:
Year: 2011 PMID: 22219945 PMCID: PMC3247327 DOI: 10.1107/S1600536811040037
Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN: 1600-5368
| C12H9F2N3O | |
| Triclinic, | Melting point: 362.15 K |
| Mo | |
| Cell parameters from 2449 reflections | |
| θ = 4.9–52.5° | |
| α = 73.652 (1)° | µ = 0.12 mm−1 |
| β = 84.202 (2)° | |
| γ = 69.260 (1)° | Block, colourless |
| 0.49 × 0.40 × 0.38 mm | |
| Rigaku R-AXIS CCD detector diffractometer | 4080 independent reflections |
| Radiation source: fine-focus sealed tube | 2816 reflections with |
| graphite | |
| φ and ω scans | θmax = 25.0°, θmin = 2.4° |
| Absorption correction: multi-scan ( | |
| 5900 measured reflections |
| Refinement on | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| H-atom parameters constrained | |
| (Δ/σ)max < 0.001 | |
| 4080 reflections | Δρmax = 0.14 e Å−3 |
| 326 parameters | Δρmin = −0.16 e Å−3 |
| 0 restraints | Extinction correction: |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0200 (19) |
| 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 |
| F1 | 1.40947 (15) | 0.64219 (16) | 0.00685 (15) | 0.1017 (5) | |
| F2 | 0.96387 (13) | 0.81942 (11) | 0.18986 (12) | 0.0717 (4) | |
| F3 | 0.93617 (18) | 0.62666 (18) | 0.51796 (17) | 0.1195 (6) | |
| F4 | 0.49568 (16) | 0.58407 (11) | 0.69708 (13) | 0.0857 (4) | |
| C1 | 1.2783 (2) | 0.6334 (2) | 0.0552 (2) | 0.0647 (6) | |
| C2 | 1.2443 (2) | 0.5265 (2) | 0.0588 (2) | 0.0668 (6) | |
| H2A | 1.3102 | 0.4597 | 0.0302 | 0.080* | |
| C3 | 1.1099 (2) | 0.52091 (19) | 0.10591 (18) | 0.0584 (5) | |
| H3A | 1.0851 | 0.4485 | 0.1102 | 0.070* | |
| C4 | 1.0094 (2) | 0.62149 (17) | 0.14757 (16) | 0.0478 (5) | |
| C5 | 1.0544 (2) | 0.72398 (18) | 0.14347 (17) | 0.0512 (5) | |
| C6 | 1.1876 (2) | 0.7330 (2) | 0.09827 (18) | 0.0591 (6) | |
| H6A | 1.2151 | 0.8033 | 0.0969 | 0.071* | |
| C7 | 0.8640 (2) | 0.61067 (19) | 0.19488 (18) | 0.0556 (5) | |
| C8 | 0.7238 (2) | 0.72473 (17) | 0.16397 (16) | 0.0463 (5) | |
| C9 | 0.5788 (2) | 0.7042 (2) | 0.1994 (2) | 0.0678 (6) | |
| H9A | 0.4949 | 0.7541 | 0.1470 | 0.081* | |
| H9B | 0.5817 | 0.6175 | 0.2403 | 0.081* | |
| C10 | 0.6327 (3) | 0.7735 (2) | 0.26206 (19) | 0.0700 (6) | |
| H10A | 0.6689 | 0.7291 | 0.3413 | 0.084* | |
| H10B | 0.5820 | 0.8658 | 0.2480 | 0.084* | |
| N2 | 0.7482 (2) | 0.78048 (16) | −0.04611 (14) | 0.0591 (5) | |
| N3 | 0.7144 (2) | 0.99200 (16) | −0.08345 (15) | 0.0647 (5) | |
| C13 | 0.8010 (3) | 0.6783 (3) | 0.5629 (2) | 0.0762 (7) | |
| C14 | 0.7534 (3) | 0.8061 (2) | 0.5600 (2) | 0.0788 (7) | |
| H14A | 0.8135 | 0.8558 | 0.5296 | 0.095* | |
| C15 | 0.6152 (3) | 0.8589 (2) | 0.6032 (2) | 0.0691 (7) | |
| H15A | 0.5821 | 0.9455 | 0.6030 | 0.083* | |
| C16 | 0.5225 (2) | 0.78710 (18) | 0.64746 (18) | 0.0573 (6) | |
| C17 | 0.5794 (3) | 0.65813 (19) | 0.64870 (19) | 0.0604 (6) | |
| C18 | 0.7182 (3) | 0.6007 (2) | 0.6075 (2) | 0.0690 (6) | |
| H18A | 0.7540 | 0.5134 | 0.6100 | 0.083* | |
| C19 | 0.3729 (3) | 0.8500 (2) | 0.69230 (19) | 0.0678 (6) | |
| C20 | 0.2382 (2) | 0.83360 (19) | 0.65607 (17) | 0.0582 (5) | |
| C21 | 0.1380 (3) | 0.7875 (3) | 0.7494 (2) | 0.0928 (9) | |
| H21A | 0.0900 | 0.7320 | 0.7342 | 0.111* | |
| H21B | 0.1660 | 0.7684 | 0.8303 | 0.111* | |
| C22 | 0.0889 (3) | 0.9228 (3) | 0.6814 (2) | 0.0884 (8) | |
| H22A | 0.0864 | 0.9871 | 0.7204 | 0.106* | |
| H22B | 0.0105 | 0.9507 | 0.6244 | 0.106* | |
| N6 | 0.2577 (2) | 0.69776 (17) | 0.41577 (15) | 0.0633 (5) | |
| N5 | 0.26550 (18) | 0.87964 (14) | 0.44550 (14) | 0.0533 (4) | |
| C12 | 0.7074 (2) | 0.94269 (18) | 0.02927 (17) | 0.0536 (5) | |
| H12A | 0.6907 | 0.9894 | 0.0846 | 0.064* | |
| C11 | 0.7406 (3) | 0.8883 (2) | −0.12474 (18) | 0.0662 (6) | |
| H11A | 0.7525 | 0.8930 | −0.2042 | 0.079* | |
| N1 | 0.72688 (16) | 0.81780 (13) | 0.05495 (12) | 0.0423 (4) | |
| N4 | 0.25081 (17) | 0.79612 (14) | 0.54907 (13) | 0.0464 (4) | |
| C24 | 0.2467 (2) | 0.68990 (19) | 0.52741 (19) | 0.0588 (5) | |
| H24A | 0.2371 | 0.6190 | 0.5847 | 0.071* | |
| C23 | 0.2694 (2) | 0.81488 (19) | 0.37037 (18) | 0.0542 (5) | |
| H23A | 0.2797 | 0.8479 | 0.2904 | 0.065* | |
| O1 | 0.85746 (19) | 0.50900 (16) | 0.25590 (17) | 0.0984 (6) | |
| O2 | 0.3590 (2) | 0.9191 (2) | 0.75643 (18) | 0.1132 (7) |
| F1 | 0.0625 (9) | 0.1236 (13) | 0.1359 (14) | −0.0376 (9) | 0.0205 (9) | −0.0597 (11) |
| F2 | 0.0660 (8) | 0.0637 (8) | 0.0980 (10) | −0.0180 (6) | −0.0012 (7) | −0.0458 (7) |
| F3 | 0.0818 (12) | 0.1246 (14) | 0.1586 (17) | −0.0256 (10) | −0.0010 (10) | −0.0595 (13) |
| F4 | 0.1023 (11) | 0.0479 (7) | 0.1065 (11) | −0.0320 (7) | −0.0159 (8) | −0.0061 (7) |
| C1 | 0.0459 (12) | 0.0778 (16) | 0.0745 (15) | −0.0183 (11) | −0.0014 (10) | −0.0297 (13) |
| C2 | 0.0566 (14) | 0.0630 (14) | 0.0824 (16) | −0.0086 (11) | −0.0069 (11) | −0.0345 (12) |
| C3 | 0.0601 (13) | 0.0419 (11) | 0.0718 (14) | −0.0118 (10) | −0.0159 (11) | −0.0146 (10) |
| C4 | 0.0504 (11) | 0.0401 (10) | 0.0495 (11) | −0.0122 (9) | −0.0116 (9) | −0.0065 (8) |
| C5 | 0.0519 (12) | 0.0468 (11) | 0.0566 (12) | −0.0101 (9) | −0.0101 (9) | −0.0215 (9) |
| C6 | 0.0542 (13) | 0.0580 (13) | 0.0741 (15) | −0.0230 (10) | −0.0108 (11) | −0.0225 (11) |
| C7 | 0.0643 (13) | 0.0430 (12) | 0.0546 (12) | −0.0207 (10) | −0.0066 (10) | −0.0001 (9) |
| C8 | 0.0522 (11) | 0.0431 (11) | 0.0444 (11) | −0.0203 (9) | −0.0006 (9) | −0.0075 (8) |
| C9 | 0.0594 (13) | 0.0629 (14) | 0.0797 (16) | −0.0295 (11) | 0.0040 (11) | −0.0068 (12) |
| C10 | 0.0797 (16) | 0.0751 (15) | 0.0522 (13) | −0.0272 (13) | 0.0119 (11) | −0.0155 (11) |
| N2 | 0.0828 (13) | 0.0495 (10) | 0.0472 (10) | −0.0189 (9) | −0.0041 (8) | −0.0197 (8) |
| N3 | 0.0933 (14) | 0.0466 (10) | 0.0496 (11) | −0.0238 (9) | −0.0031 (9) | −0.0048 (8) |
| C13 | 0.0669 (16) | 0.0743 (17) | 0.0896 (18) | −0.0180 (14) | −0.0208 (13) | −0.0258 (14) |
| C14 | 0.0871 (19) | 0.0678 (16) | 0.0901 (18) | −0.0367 (15) | −0.0249 (15) | −0.0121 (14) |
| C15 | 0.0893 (18) | 0.0437 (12) | 0.0798 (16) | −0.0221 (12) | −0.0336 (14) | −0.0140 (11) |
| C16 | 0.0774 (15) | 0.0406 (11) | 0.0577 (13) | −0.0164 (10) | −0.0262 (11) | −0.0146 (9) |
| C17 | 0.0800 (16) | 0.0407 (11) | 0.0635 (14) | −0.0227 (11) | −0.0236 (11) | −0.0075 (10) |
| C18 | 0.0771 (16) | 0.0447 (12) | 0.0835 (16) | −0.0082 (12) | −0.0308 (13) | −0.0198 (11) |
| C19 | 0.0935 (18) | 0.0516 (13) | 0.0608 (14) | −0.0151 (12) | −0.0176 (12) | −0.0253 (11) |
| C20 | 0.0743 (14) | 0.0527 (12) | 0.0469 (12) | −0.0143 (11) | −0.0016 (10) | −0.0210 (10) |
| C21 | 0.117 (2) | 0.112 (2) | 0.0538 (15) | −0.0430 (19) | 0.0201 (14) | −0.0304 (15) |
| C22 | 0.0852 (18) | 0.094 (2) | 0.0825 (18) | −0.0074 (15) | 0.0070 (14) | −0.0493 (16) |
| N6 | 0.0885 (13) | 0.0544 (11) | 0.0570 (11) | −0.0311 (10) | 0.0008 (9) | −0.0215 (9) |
| N5 | 0.0702 (11) | 0.0415 (9) | 0.0490 (10) | −0.0234 (8) | 0.0010 (8) | −0.0078 (8) |
| C12 | 0.0735 (14) | 0.0383 (11) | 0.0507 (12) | −0.0181 (10) | −0.0012 (10) | −0.0151 (9) |
| C11 | 0.0932 (17) | 0.0598 (14) | 0.0409 (12) | −0.0215 (12) | −0.0025 (11) | −0.0111 (11) |
| N1 | 0.0511 (9) | 0.0361 (8) | 0.0403 (8) | −0.0138 (7) | −0.0024 (7) | −0.0117 (7) |
| N4 | 0.0597 (10) | 0.0391 (8) | 0.0428 (9) | −0.0187 (7) | −0.0004 (7) | −0.0121 (7) |
| C24 | 0.0857 (15) | 0.0456 (12) | 0.0534 (13) | −0.0350 (11) | 0.0014 (10) | −0.0105 (9) |
| C23 | 0.0663 (13) | 0.0528 (12) | 0.0447 (11) | −0.0221 (10) | 0.0050 (9) | −0.0140 (9) |
| O1 | 0.0834 (12) | 0.0565 (10) | 0.1217 (15) | −0.0247 (9) | −0.0031 (10) | 0.0301 (10) |
| O2 | 0.1266 (16) | 0.1143 (15) | 0.1246 (16) | −0.0233 (12) | −0.0190 (12) | −0.0879 (14) |
| F1—C1 | 1.357 (3) | C13—C14 | 1.365 (3) |
| F2—C5 | 1.354 (2) | C14—C15 | 1.364 (3) |
| F3—C13 | 1.348 (3) | C14—H14A | 0.9300 |
| F4—C17 | 1.348 (2) | C15—C16 | 1.390 (3) |
| C1—C6 | 1.366 (3) | C15—H15A | 0.9300 |
| C1—C2 | 1.366 (3) | C16—C17 | 1.382 (3) |
| C2—C3 | 1.371 (3) | C16—C19 | 1.483 (3) |
| C2—H2A | 0.9300 | C17—C18 | 1.371 (3) |
| C3—C4 | 1.396 (3) | C18—H18A | 0.9300 |
| C3—H3A | 0.9300 | C19—O2 | 1.215 (2) |
| C4—C5 | 1.378 (3) | C19—C20 | 1.493 (3) |
| C4—C7 | 1.486 (3) | C20—N4 | 1.437 (2) |
| C5—C6 | 1.364 (3) | C20—C22 | 1.498 (3) |
| C6—H6A | 0.9300 | C20—C21 | 1.502 (3) |
| C7—O1 | 1.209 (2) | C21—C22 | 1.464 (4) |
| C7—C8 | 1.498 (3) | C21—H21A | 0.9700 |
| C8—N1 | 1.436 (2) | C21—H21B | 0.9700 |
| C8—C9 | 1.494 (3) | C22—H22A | 0.9700 |
| C8—C10 | 1.503 (3) | C22—H22B | 0.9700 |
| C9—C10 | 1.470 (3) | N6—C24 | 1.303 (3) |
| C9—H9A | 0.9700 | N6—C23 | 1.342 (3) |
| C9—H9B | 0.9700 | N5—C23 | 1.305 (2) |
| C10—H10A | 0.9700 | N5—N4 | 1.363 (2) |
| C10—H10B | 0.9700 | C12—N1 | 1.327 (2) |
| N2—C11 | 1.309 (3) | C12—H12A | 0.9300 |
| N2—N1 | 1.361 (2) | C11—H11A | 0.9300 |
| N3—C12 | 1.307 (2) | N4—C24 | 1.330 (2) |
| N3—C11 | 1.348 (3) | C24—H24A | 0.9300 |
| C13—C18 | 1.364 (3) | C23—H23A | 0.9300 |
| F1—C1—C6 | 117.4 (2) | C17—C16—C15 | 116.4 (2) |
| F1—C1—C2 | 118.9 (2) | C17—C16—C19 | 124.0 (2) |
| C6—C1—C2 | 123.7 (2) | C15—C16—C19 | 119.55 (19) |
| C1—C2—C3 | 117.9 (2) | F4—C17—C18 | 118.42 (19) |
| C1—C2—H2A | 121.1 | F4—C17—C16 | 117.9 (2) |
| C3—C2—H2A | 121.1 | C18—C17—C16 | 123.6 (2) |
| C2—C3—C4 | 121.47 (19) | C13—C18—C17 | 116.4 (2) |
| C2—C3—H3A | 119.3 | C13—C18—H18A | 121.8 |
| C4—C3—H3A | 119.3 | C17—C18—H18A | 121.8 |
| C5—C4—C3 | 116.77 (19) | O2—C19—C16 | 119.7 (2) |
| C5—C4—C7 | 124.50 (17) | O2—C19—C20 | 119.5 (2) |
| C3—C4—C7 | 118.72 (17) | C16—C19—C20 | 120.83 (17) |
| F2—C5—C6 | 117.88 (17) | N4—C20—C19 | 116.14 (18) |
| F2—C5—C4 | 118.42 (18) | N4—C20—C22 | 116.23 (18) |
| C6—C5—C4 | 123.66 (18) | C19—C20—C22 | 117.79 (19) |
| C5—C6—C1 | 116.47 (19) | N4—C20—C21 | 117.26 (19) |
| C5—C6—H6A | 121.8 | C19—C20—C21 | 118.64 (19) |
| C1—C6—H6A | 121.8 | C22—C20—C21 | 58.42 (17) |
| O1—C7—C4 | 120.29 (19) | C22—C21—C20 | 60.67 (17) |
| O1—C7—C8 | 119.54 (19) | C22—C21—H21A | 117.7 |
| C4—C7—C8 | 120.14 (16) | C20—C21—H21A | 117.7 |
| N1—C8—C9 | 116.98 (16) | C22—C21—H21B | 117.7 |
| N1—C8—C7 | 115.56 (15) | C20—C21—H21B | 117.7 |
| C9—C8—C7 | 118.05 (17) | H21A—C21—H21B | 114.8 |
| N1—C8—C10 | 117.75 (16) | C21—C22—C20 | 60.91 (16) |
| C9—C8—C10 | 58.74 (14) | C21—C22—H22A | 117.7 |
| C7—C8—C10 | 117.95 (17) | C20—C22—H22A | 117.7 |
| C10—C9—C8 | 60.96 (14) | C21—C22—H22B | 117.7 |
| C10—C9—H9A | 117.7 | C20—C22—H22B | 117.7 |
| C8—C9—H9A | 117.7 | H22A—C22—H22B | 114.8 |
| C10—C9—H9B | 117.7 | C24—N6—C23 | 102.17 (16) |
| C8—C9—H9B | 117.7 | C23—N5—N4 | 102.04 (15) |
| H9A—C9—H9B | 114.8 | N3—C12—N1 | 111.64 (17) |
| C9—C10—C8 | 60.30 (14) | N3—C12—H12A | 124.2 |
| C9—C10—H10A | 117.7 | N1—C12—H12A | 124.2 |
| C8—C10—H10A | 117.7 | N2—C11—N3 | 115.84 (18) |
| C9—C10—H10B | 117.7 | N2—C11—H11A | 122.1 |
| C8—C10—H10B | 117.7 | N3—C11—H11A | 122.1 |
| H10A—C10—H10B | 114.9 | C12—N1—N2 | 108.90 (15) |
| C11—N2—N1 | 101.85 (15) | C12—N1—C8 | 132.04 (15) |
| C12—N3—C11 | 101.76 (17) | N2—N1—C8 | 119.02 (14) |
| F3—C13—C18 | 118.3 (2) | C24—N4—N5 | 108.55 (15) |
| F3—C13—C14 | 118.2 (3) | C24—N4—C20 | 131.78 (17) |
| C18—C13—C14 | 123.4 (3) | N5—N4—C20 | 119.64 (15) |
| C15—C14—C13 | 118.1 (2) | N6—C24—N4 | 111.46 (18) |
| C15—C14—H14A | 120.9 | N6—C24—H24A | 124.3 |
| C13—C14—H14A | 120.9 | N4—C24—H24A | 124.3 |
| C14—C15—C16 | 122.0 (2) | N5—C23—N6 | 115.78 (18) |
| C14—C15—H15A | 119.0 | N5—C23—H23A | 122.1 |
| C16—C15—H15A | 119.0 | N6—C23—H23A | 122.1 |
| F1—C1—C2—C3 | −178.8 (2) | C17—C16—C19—O2 | 132.8 (2) |
| C6—C1—C2—C3 | 1.6 (4) | C15—C16—C19—O2 | −45.8 (3) |
| C1—C2—C3—C4 | 0.9 (3) | C17—C16—C19—C20 | −49.5 (3) |
| C2—C3—C4—C5 | −2.6 (3) | C15—C16—C19—C20 | 131.9 (2) |
| C2—C3—C4—C7 | 178.48 (19) | O2—C19—C20—N4 | 156.3 (2) |
| C3—C4—C5—F2 | −175.89 (17) | C16—C19—C20—N4 | −21.4 (3) |
| C7—C4—C5—F2 | 2.9 (3) | O2—C19—C20—C22 | 11.7 (3) |
| C3—C4—C5—C6 | 2.1 (3) | C16—C19—C20—C22 | −166.0 (2) |
| C7—C4—C5—C6 | −179.09 (19) | O2—C19—C20—C21 | −55.6 (3) |
| F2—C5—C6—C1 | 178.18 (18) | C16—C19—C20—C21 | 126.7 (2) |
| C4—C5—C6—C1 | 0.2 (3) | N4—C20—C21—C22 | −105.5 (2) |
| F1—C1—C6—C5 | 178.23 (19) | C19—C20—C21—C22 | 106.7 (2) |
| C2—C1—C6—C5 | −2.1 (3) | N4—C20—C22—C21 | 107.2 (2) |
| C5—C4—C7—O1 | −137.7 (2) | C19—C20—C22—C21 | −108.2 (2) |
| C3—C4—C7—O1 | 41.0 (3) | C11—N3—C12—N1 | −0.4 (2) |
| C5—C4—C7—C8 | 44.3 (3) | N1—N2—C11—N3 | −0.8 (3) |
| C3—C4—C7—C8 | −136.94 (19) | C12—N3—C11—N2 | 0.8 (3) |
| O1—C7—C8—N1 | −152.1 (2) | N3—C12—N1—N2 | −0.1 (2) |
| C4—C7—C8—N1 | 25.9 (2) | N3—C12—N1—C8 | −177.66 (18) |
| O1—C7—C8—C9 | −6.6 (3) | C11—N2—N1—C12 | 0.5 (2) |
| C4—C7—C8—C9 | 171.43 (17) | C11—N2—N1—C8 | 178.46 (17) |
| O1—C7—C8—C10 | 60.9 (3) | C9—C8—N1—C12 | 93.1 (2) |
| C4—C7—C8—C10 | −121.1 (2) | C7—C8—N1—C12 | −121.0 (2) |
| N1—C8—C9—C10 | −107.59 (19) | C10—C8—N1—C12 | 26.0 (3) |
| C7—C8—C9—C10 | 107.3 (2) | C9—C8—N1—N2 | −84.3 (2) |
| N1—C8—C10—C9 | 106.28 (19) | C7—C8—N1—N2 | 61.6 (2) |
| C7—C8—C10—C9 | −107.5 (2) | C10—C8—N1—N2 | −151.36 (17) |
| F3—C13—C14—C15 | 178.6 (2) | C23—N5—N4—C24 | −0.2 (2) |
| C18—C13—C14—C15 | −0.7 (4) | C23—N5—N4—C20 | −178.35 (17) |
| C13—C14—C15—C16 | −1.0 (3) | C19—C20—N4—C24 | 115.3 (2) |
| C14—C15—C16—C17 | 1.9 (3) | C22—C20—N4—C24 | −99.5 (3) |
| C14—C15—C16—C19 | −179.5 (2) | C21—C20—N4—C24 | −33.2 (3) |
| C15—C16—C17—F4 | 176.35 (18) | C19—C20—N4—N5 | −67.0 (2) |
| C19—C16—C17—F4 | −2.2 (3) | C22—C20—N4—N5 | 78.1 (2) |
| C15—C16—C17—C18 | −1.1 (3) | C21—C20—N4—N5 | 144.4 (2) |
| C19—C16—C17—C18 | −179.7 (2) | C23—N6—C24—N4 | 0.2 (2) |
| F3—C13—C18—C17 | −177.9 (2) | N5—N4—C24—N6 | 0.0 (2) |
| C14—C13—C18—C17 | 1.4 (3) | C20—N4—C24—N6 | 177.81 (19) |
| F4—C17—C18—C13 | −177.89 (19) | N4—N5—C23—N6 | 0.4 (2) |
| C16—C17—C18—C13 | −0.5 (3) | C24—N6—C23—N5 | −0.4 (2) |
| H··· | ||||
| C12—H12A···O2i | 0.93 | 2.35 | 3.268 (2) | 171. |
| C24—H24A···O1ii | 0.93 | 2.37 | 3.265 (3) | 161. |
Hydrogen-bond geometry (Å, °)
| H⋯ | ||||
|---|---|---|---|---|
| C12—H12 | 0.93 | 2.35 | 3.268 (2) | 171 |
| C24—H24 | 0.93 | 2.37 | 3.265 (3) | 161 |
Symmetry codes: (i) ; (ii) .