Acta Cryst. (2007). E63, o3949 [ doi:10.1107/S1600536807041967 ]
In the molecule of the title compound, C21H15FN4O3, intramolecular C-H
O and C-HF hydrogen bonds result in the formation of one six- and one five-membered ring. In the crystal structure, intermolecular C-HO hydrogen bonds link the molecules into chains along the a axis. The packing is further stabilized by ![[pi]](http://journals.iucr.org/logos/entities/pi_rmgif.gif)
- interactions [centroid-centroid distance 3.632 (2) Å].
The title compound was prepared according to the literature method (Han et al., 2007). Single crystals suitable for X-ray analysis were obtained by slow evaporation of an ethyl acetate solution at room temperature over a period of 6 d.
H atoms were positioned geometrically with C—H = 0.93, 0.98 and 0.97 Å for aromatic, methine and methylene H atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C)
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b), PARST (Nardelli, 1995) and PLATON (Spek, 2003).
![[Figure 1]](./hk2319fig1thm.gif)
| Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. |
![[Figure 2]](./hk2319fig2thm.gif)
| Fig. 2. A packing diagram for (I). Hydrogen bonds are shown as dashed lines. |
| C21H15FN4O3 | Z = 2 |
| Mr = 390.37 | F000 = 404 |
| Triclinic, P1 | Dx = 1.398 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation λ = 0.71073 Å |
| a = 9.8423 (9) Å | Cell parameters from 2193 reflections |
| b = 9.9736 (10) Å | θ = 2.3–24.9º |
| c = 11.4000 (11) Å | µ = 0.10 mm−1 |
| α = 64.459 (1)º | T = 298 (2) K |
| β = 67.157 (1)º | Block, yellow |
| γ = 76.313 (1)º | 0.36 × 0.30 × 0.26 mm |
| V = 927.28 (15) Å3 |
| Siemens SMART 1000 CCD area-detector diffractometer | 3560 independent reflections |
| Radiation source: fine-focus sealed tube | 2877 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.013 |
| Detector resolution: 8.33 pixels mm-1 | θmax = 26.0º |
| T = 293(2) K | θmin = 2.1º |
| ω scans | h = −12→6 |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −12→12 |
| Tmin = 0.964, Tmax = 0.974 | l = −14→14 |
| 5202 measured reflections |
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.042 | w = 1/[σ2(Fo2) + (0.0541P)2 + 0.1733P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.114 | (Δ/σ)max < 0.001 |
| S = 1.05 | Δρmax = 0.14 e Å−3 |
| 3560 reflections | Δρmin = −0.18 e Å−3 |
| 263 parameters | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.026 (3) |
| Secondary atom site location: difference Fourier map |
| C21H15FN4O3 | γ = 76.313 (1)º |
| Mr = 390.37 | V = 927.28 (15) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 9.8423 (9) Å | Mo Kα |
| b = 9.9736 (10) Å | µ = 0.10 mm−1 |
| c = 11.4000 (11) Å | T = 298 (2) K |
| α = 64.459 (1)º | 0.36 × 0.30 × 0.26 mm |
| β = 67.157 (1)º |
| Siemens SMART 1000 CCD area-detector diffractometer | 3560 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2877 reflections with I > 2σ(I) |
| Tmin = 0.964, Tmax = 0.974 | Rint = 0.013 |
| 5202 measured reflections |
| R[F2 > 2σ(F2)] = 0.042 | 263 parameters |
| wR(F2) = 0.114 | H-atom parameters constrained |
| S = 1.05 | Δρmax = 0.14 e Å−3 |
| 3560 reflections | Δρmin = −0.18 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 F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R– factors based on ALL data will be even larger. |
| x | y | z | Uiso*/Ueq | ||
| F1 | 0.89959 (13) | 0.26256 (12) | −0.41995 (10) | 0.0754 (4) | |
| O1 | 0.65340 (14) | −0.09185 (13) | −0.12652 (11) | 0.0621 (3) | |
| O2 | 0.72673 (11) | 0.03294 (11) | −0.00182 (9) | 0.0444 (3) | |
| O3 | 0.94370 (14) | −0.10059 (14) | −0.05293 (12) | 0.0660 (4) | |
| N1 | 0.68866 (14) | 0.36422 (13) | −0.13452 (12) | 0.0433 (3) | |
| N2 | 0.77269 (15) | 0.47243 (14) | −0.24241 (14) | 0.0539 (4) | |
| N3 | 0.80732 (16) | 0.55330 (15) | −0.19591 (15) | 0.0592 (4) | |
| N4 | 0.59613 (19) | −0.25912 (19) | 0.39906 (15) | 0.0761 (5) | |
| C1 | 0.85535 (18) | 0.17262 (17) | −0.45709 (16) | 0.0487 (4) | |
| C2 | 0.9011 (2) | 0.2013 (2) | −0.59553 (17) | 0.0607 (5) | |
| H2B | 0.9598 | 0.2790 | −0.6596 | 0.073* | |
| C3 | 0.8578 (2) | 0.1122 (2) | −0.63630 (19) | 0.0696 (5) | |
| H3B | 0.8860 | 0.1305 | −0.7294 | 0.084* | |
| C4 | 0.7734 (2) | −0.0035 (3) | −0.5410 (2) | 0.0749 (6) | |
| H4B | 0.7447 | −0.0634 | −0.5697 | 0.090* | |
| C5 | 0.73070 (19) | −0.0316 (2) | −0.40328 (18) | 0.0592 (5) | |
| H5A | 0.6746 | −0.1115 | −0.3398 | 0.071* | |
| C6 | 0.76984 (16) | 0.05731 (16) | −0.35668 (15) | 0.0420 (3) | |
| C7 | 0.72116 (16) | 0.01687 (16) | −0.20536 (15) | 0.0416 (3) | |
| C8 | 0.75139 (16) | 0.11471 (15) | −0.14647 (14) | 0.0406 (3) | |
| H8A | 0.8533 | 0.1432 | −0.1937 | 0.049* | |
| C9 | 0.64266 (17) | 0.25315 (16) | −0.15857 (15) | 0.0430 (3) | |
| H9A | 0.6338 | 0.2963 | −0.2498 | 0.052* | |
| H9B | 0.5460 | 0.2246 | −0.0924 | 0.052* | |
| C10 | 0.66910 (16) | 0.37656 (15) | −0.01425 (15) | 0.0424 (3) | |
| C11 | 0.74604 (18) | 0.49795 (17) | −0.05488 (18) | 0.0501 (4) | |
| C12 | 0.7507 (2) | 0.5446 (2) | 0.0431 (2) | 0.0672 (5) | |
| H12A | 0.8022 | 0.6253 | 0.0175 | 0.081* | |
| C13 | 0.6769 (2) | 0.4668 (2) | 0.1771 (2) | 0.0705 (5) | |
| H13A | 0.6782 | 0.4951 | 0.2444 | 0.085* | |
| C14 | 0.5989 (2) | 0.3452 (2) | 0.21693 (19) | 0.0648 (5) | |
| H14A | 0.5497 | 0.2954 | 0.3098 | 0.078* | |
| C15 | 0.59284 (19) | 0.29725 (18) | 0.12321 (16) | 0.0532 (4) | |
| H15A | 0.5409 | 0.2166 | 0.1497 | 0.064* | |
| C16 | 0.82944 (17) | −0.07994 (16) | 0.03048 (15) | 0.0424 (3) | |
| C17 | 0.78394 (16) | −0.17652 (15) | 0.17859 (15) | 0.0413 (3) | |
| C18 | 0.64180 (19) | −0.16715 (19) | 0.26721 (16) | 0.0554 (4) | |
| H18A | 0.5741 | −0.0926 | 0.2332 | 0.066* | |
| C19 | 0.6977 (3) | −0.3626 (2) | 0.44441 (19) | 0.0743 (6) | |
| H19A | 0.6687 | −0.4275 | 0.5360 | 0.089* | |
| C20 | 0.8409 (2) | −0.37952 (19) | 0.36566 (19) | 0.0638 (5) | |
| H20A | 0.9073 | −0.4527 | 0.4033 | 0.077* | |
| C21 | 0.88514 (19) | −0.28663 (17) | 0.22992 (17) | 0.0528 (4) | |
| H21A | 0.9815 | −0.2972 | 0.1731 | 0.063* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| F1 | 0.1104 (9) | 0.0647 (7) | 0.0472 (6) | −0.0452 (6) | −0.0100 (6) | −0.0125 (5) |
| O1 | 0.0804 (8) | 0.0543 (7) | 0.0468 (7) | −0.0304 (6) | −0.0125 (6) | −0.0097 (5) |
| O2 | 0.0525 (6) | 0.0432 (6) | 0.0325 (5) | 0.0024 (5) | −0.0155 (5) | −0.0117 (4) |
| O3 | 0.0592 (7) | 0.0693 (8) | 0.0489 (7) | 0.0123 (6) | −0.0107 (6) | −0.0192 (6) |
| N1 | 0.0509 (7) | 0.0341 (6) | 0.0392 (7) | −0.0053 (5) | −0.0133 (6) | −0.0090 (5) |
| N2 | 0.0618 (8) | 0.0377 (7) | 0.0470 (8) | −0.0077 (6) | −0.0109 (6) | −0.0067 (6) |
| N3 | 0.0655 (9) | 0.0405 (7) | 0.0637 (9) | −0.0134 (6) | −0.0132 (7) | −0.0150 (7) |
| N4 | 0.0797 (11) | 0.0737 (11) | 0.0437 (8) | 0.0012 (9) | −0.0101 (8) | −0.0072 (8) |
| C1 | 0.0556 (9) | 0.0452 (8) | 0.0424 (8) | −0.0058 (7) | −0.0139 (7) | −0.0152 (7) |
| C2 | 0.0640 (11) | 0.0623 (11) | 0.0390 (9) | −0.0032 (9) | −0.0076 (8) | −0.0133 (8) |
| C3 | 0.0701 (12) | 0.0952 (15) | 0.0451 (10) | 0.0061 (11) | −0.0163 (9) | −0.0368 (10) |
| C4 | 0.0765 (13) | 0.1037 (16) | 0.0658 (12) | −0.0143 (12) | −0.0180 (10) | −0.0523 (12) |
| C5 | 0.0573 (10) | 0.0714 (11) | 0.0567 (10) | −0.0162 (9) | −0.0099 (8) | −0.0334 (9) |
| C6 | 0.0418 (8) | 0.0440 (8) | 0.0396 (8) | −0.0017 (6) | −0.0125 (6) | −0.0169 (6) |
| C7 | 0.0432 (8) | 0.0391 (7) | 0.0398 (8) | −0.0059 (6) | −0.0135 (6) | −0.0112 (6) |
| C8 | 0.0461 (8) | 0.0405 (8) | 0.0317 (7) | −0.0070 (6) | −0.0117 (6) | −0.0098 (6) |
| C9 | 0.0489 (8) | 0.0402 (8) | 0.0398 (8) | −0.0040 (6) | −0.0180 (7) | −0.0116 (6) |
| C10 | 0.0435 (8) | 0.0372 (7) | 0.0462 (8) | 0.0025 (6) | −0.0169 (7) | −0.0166 (6) |
| C11 | 0.0509 (9) | 0.0380 (8) | 0.0607 (10) | −0.0013 (7) | −0.0186 (8) | −0.0189 (7) |
| C12 | 0.0780 (13) | 0.0521 (10) | 0.0888 (15) | −0.0037 (9) | −0.0355 (11) | −0.0356 (10) |
| C13 | 0.0881 (14) | 0.0685 (12) | 0.0761 (14) | 0.0069 (11) | −0.0382 (11) | −0.0431 (11) |
| C14 | 0.0776 (13) | 0.0669 (11) | 0.0501 (10) | 0.0029 (10) | −0.0199 (9) | −0.0275 (9) |
| C15 | 0.0581 (10) | 0.0512 (9) | 0.0469 (9) | −0.0086 (8) | −0.0127 (8) | −0.0176 (7) |
| C16 | 0.0473 (8) | 0.0415 (8) | 0.0420 (8) | 0.0001 (6) | −0.0176 (7) | −0.0185 (7) |
| C17 | 0.0503 (8) | 0.0387 (7) | 0.0411 (8) | −0.0015 (6) | −0.0210 (7) | −0.0163 (6) |
| C18 | 0.0585 (10) | 0.0539 (9) | 0.0438 (9) | 0.0045 (8) | −0.0190 (8) | −0.0124 (7) |
| C19 | 0.1031 (17) | 0.0611 (11) | 0.0426 (10) | −0.0030 (11) | −0.0272 (11) | −0.0043 (8) |
| C20 | 0.0812 (13) | 0.0489 (10) | 0.0616 (11) | 0.0050 (9) | −0.0412 (10) | −0.0109 (8) |
| C21 | 0.0559 (10) | 0.0469 (9) | 0.0571 (10) | 0.0020 (7) | −0.0272 (8) | −0.0165 (8) |
| F1—C1 | 1.3525 (19) | C8—H8A | 0.9800 |
| O1—C7 | 1.2103 (17) | C9—H9A | 0.9700 |
| O2—C8 | 1.4376 (16) | C9—H9B | 0.9700 |
| O2—C16 | 1.3482 (17) | C10—C11 | 1.390 (2) |
| O3—C16 | 1.2001 (18) | C10—C15 | 1.394 (2) |
| N1—N2 | 1.3600 (17) | C11—C12 | 1.401 (3) |
| N1—C9 | 1.4501 (19) | C12—H12A | 0.9300 |
| N1—C10 | 1.3643 (19) | C13—C12 | 1.359 (3) |
| N3—N2 | 1.299 (2) | C13—H13A | 0.9300 |
| N3—C11 | 1.376 (2) | C14—C15 | 1.370 (2) |
| N4—C19 | 1.336 (2) | C14—C13 | 1.401 (3) |
| C1—C2 | 1.377 (2) | C14—H14A | 0.9300 |
| C2—C3 | 1.369 (3) | C15—H15A | 0.9300 |
| C2—H2B | 0.9300 | C16—C17 | 1.481 (2) |
| C3—C4 | 1.369 (3) | C17—C18 | 1.382 (2) |
| C3—H3B | 0.9300 | C17—C21 | 1.386 (2) |
| C4—H4B | 0.9300 | C18—N4 | 1.336 (2) |
| C5—C4 | 1.372 (3) | C18—H18A | 0.9300 |
| C5—H5A | 0.9300 | C19—H19A | 0.9300 |
| C6—C1 | 1.384 (2) | C20—C19 | 1.363 (3) |
| C6—C5 | 1.394 (2) | C20—H20A | 0.9300 |
| C7—C6 | 1.489 (2) | C21—C20 | 1.369 (2) |
| C7—C8 | 1.533 (2) | C21—H21A | 0.9300 |
| C8—C9 | 1.524 (2) | ||
| C16—O2—C8 | 115.43 (11) | C8—C9—H9B | 109.2 |
| N2—N1—C10 | 109.94 (12) | H9A—C9—H9B | 107.9 |
| N2—N1—C9 | 119.71 (12) | N1—C10—C11 | 104.16 (13) |
| C10—N1—C9 | 130.22 (12) | N1—C10—C15 | 133.48 (14) |
| N3—N2—N1 | 108.89 (13) | C11—C10—C15 | 122.35 (15) |
| N2—N3—C11 | 108.38 (13) | N3—C11—C10 | 108.63 (14) |
| C18—N4—C19 | 116.17 (17) | N3—C11—C12 | 130.90 (16) |
| F1—C1—C2 | 116.89 (15) | C10—C11—C12 | 120.47 (16) |
| F1—C1—C6 | 119.52 (13) | C13—C12—C11 | 117.14 (17) |
| C2—C1—C6 | 123.58 (16) | C13—C12—H12A | 121.4 |
| C3—C2—C1 | 118.23 (17) | C11—C12—H12A | 121.4 |
| C3—C2—H2B | 120.9 | C12—C13—C14 | 121.96 (18) |
| C1—C2—H2B | 120.9 | C12—C13—H13A | 119.0 |
| C2—C3—C4 | 120.45 (17) | C14—C13—H13A | 119.0 |
| C2—C3—H3B | 119.8 | C15—C14—C13 | 122.02 (18) |
| C4—C3—H3B | 119.8 | C15—C14—H14A | 119.0 |
| C3—C4—C5 | 120.44 (18) | C13—C14—H14A | 119.0 |
| C3—C4—H4B | 119.8 | C14—C15—C10 | 116.06 (16) |
| C5—C4—H4B | 119.8 | C14—C15—H15A | 122.0 |
| C4—C5—C6 | 121.31 (17) | C10—C15—H15A | 122.0 |
| C4—C5—H5A | 119.3 | O3—C16—O2 | 123.21 (14) |
| C6—C5—H5A | 119.3 | O3—C16—C17 | 124.15 (14) |
| C1—C6—C5 | 115.97 (14) | O2—C16—C17 | 112.63 (12) |
| C1—C6—C7 | 126.34 (14) | C18—C17—C21 | 118.07 (14) |
| C5—C6—C7 | 117.65 (14) | C18—C17—C16 | 122.75 (13) |
| O1—C7—C6 | 120.59 (13) | C21—C17—C16 | 119.08 (14) |
| O1—C7—C8 | 118.64 (13) | N4—C18—C17 | 123.69 (15) |
| C6—C7—C8 | 120.73 (12) | N4—C18—H18A | 118.2 |
| O2—C8—C9 | 106.13 (11) | C17—C18—H18A | 118.2 |
| O2—C8—C7 | 108.81 (11) | N4—C19—C20 | 124.51 (17) |
| C9—C8—C7 | 110.90 (12) | N4—C19—H19A | 117.7 |
| O2—C8—H8A | 110.3 | C20—C19—H19A | 117.7 |
| C9—C8—H8A | 110.3 | C19—C20—C21 | 118.61 (16) |
| C7—C8—H8A | 110.3 | C19—C20—H20A | 120.7 |
| N1—C9—C8 | 112.17 (12) | C21—C20—H20A | 120.7 |
| N1—C9—H9A | 109.2 | C20—C21—C17 | 118.91 (16) |
| C8—C9—H9A | 109.2 | C20—C21—H21A | 120.5 |
| N1—C9—H9B | 109.2 | C17—C21—H21A | 120.5 |
| C16—O2—C8—C9 | −168.65 (11) | C8—C7—C6—C5 | −176.13 (14) |
| C16—O2—C8—C7 | 71.94 (15) | O1—C7—C8—O2 | 15.96 (19) |
| C8—O2—C16—O3 | 9.4 (2) | C6—C7—C8—O2 | −165.99 (12) |
| C8—O2—C16—C17 | −169.32 (11) | O1—C7—C8—C9 | −100.42 (16) |
| C10—N1—N2—N3 | −0.08 (17) | C6—C7—C8—C9 | 77.63 (16) |
| C9—N1—N2—N3 | −176.40 (12) | O2—C8—C9—N1 | 75.59 (14) |
| N2—N1—C9—C8 | 91.87 (15) | C7—C8—C9—N1 | −166.39 (11) |
| C10—N1—C9—C8 | −83.59 (18) | N1—C10—C11—N3 | 0.26 (16) |
| N2—N1—C10—C11 | −0.11 (15) | C15—C10—C11—N3 | −179.16 (14) |
| C9—N1—C10—C11 | 175.70 (14) | N1—C10—C11—C12 | −179.94 (14) |
| N2—N1—C10—C15 | 179.21 (16) | C15—C10—C11—C12 | 0.6 (2) |
| C9—N1—C10—C15 | −5.0 (3) | N1—C10—C15—C14 | −179.72 (16) |
| C11—N3—N2—N1 | 0.24 (17) | C11—C10—C15—C14 | −0.5 (2) |
| N2—N3—C11—C10 | −0.32 (18) | N3—C11—C12—C13 | 179.43 (17) |
| N2—N3—C11—C12 | 179.91 (17) | C10—C11—C12—C13 | −0.3 (3) |
| C18—N4—C19—C20 | −0.4 (3) | C14—C13—C12—C11 | −0.1 (3) |
| F1—C1—C2—C3 | −179.88 (15) | C13—C14—C15—C10 | 0.1 (3) |
| C6—C1—C2—C3 | 1.0 (3) | C15—C14—C13—C12 | 0.2 (3) |
| C1—C2—C3—C4 | −1.1 (3) | C18—C17—C21—C20 | −0.8 (2) |
| C2—C3—C4—C5 | 0.1 (3) | C16—C17—C21—C20 | −177.42 (15) |
| C6—C5—C4—C3 | 0.9 (3) | C21—C17—C18—N4 | −0.7 (3) |
| C5—C6—C1—F1 | −179.08 (14) | C16—C17—C18—N4 | 175.74 (16) |
| C7—C6—C1—F1 | −1.4 (2) | O3—C16—C17—C18 | −167.62 (16) |
| C5—C6—C1—C2 | 0.0 (2) | O2—C16—C17—C18 | 11.0 (2) |
| C7—C6—C1—C2 | 177.67 (15) | O3—C16—C17—C21 | 8.8 (2) |
| C1—C6—C5—C4 | −1.0 (3) | O2—C16—C17—C21 | −172.55 (13) |
| C7—C6—C5—C4 | −178.86 (17) | C17—C18—N4—C19 | 1.3 (3) |
| O1—C7—C6—C1 | −175.75 (15) | C21—C20—C19—N4 | −1.1 (3) |
| C8—C7—C6—C1 | 6.2 (2) | C17—C21—C20—C19 | 1.7 (3) |
| O1—C7—C6—C5 | 1.9 (2) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C3—H3B···O3i | 0.93 | 2.50 | 3.355 (2) | 154 |
| C8—H8A···F1 | 0.98 | 2.23 | 2.747 (2) | 112 |
| C9—H9B···O1ii | 0.97 | 2.53 | 3.464 (2) | 161 |
| C18—H18A···O2 | 0.93 | 2.43 | 2.758 (2) | 101 |
| Symmetry codes: (i) −x+2, −y, −z−1; (ii) −x+1, −y, −z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C3—H3B···O3i | 0.93 | 2.50 | 3.355 (2) | 154 |
| C8—H8A···F1 | 0.98 | 2.23 | 2.747 (2) | 112 |
| C9—H9B···O1ii | 0.97 | 2.53 | 3.464 (2) | 161 |
| C18—H18A···O2 | 0.93 | 2.43 | 2.758 (2) | 101 |
| Symmetry codes: (i) −x+2, −y, −z−1; (ii) −x+1, −y, −z. |
This project was supported by the Natural Science Foundation of Shandong Province (grant Nos. Z2006B01 and Y2006B07).
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We have recently reported the structure of 2-(1H-benzotriazol-1-yl)-1-(4 -chlorobenzoyl)ethyl isonicotinate (II) (Han et al., 2007). As part of our ongoing studies of triazole derivatives, the title compound, (I), was synthesized and its crystal structure is reported here.
In the molecule of the title compound, (I), the bond lengths and angles are generally within normal ranges (Allen et al., 1987), and are comparable to those in the related compound (II). In (I), the benzotriazole ring system is essentially planar with a dihedral angle of 0.45 (1)° between triazole A (N1—N3/C10/C11) and benzene B (C10—C15) rings. Rings C (N4/C17—C21) and D (C1—C6) are oriented with respect to the benzotriazole system at dihedral angles of 87.82 (1)° and 0.78 (1)°, respectively, while the dihedral angle between them is 87.62 (1)°. The intramolecular C—H···O and C—H···F hydrogen bonds (Table 1) cause to the formation of one six- and one five-membered rings (Fig. 1).
In the crystal structure, the intermolecular C—H···O hydrogen bonds (Table 1), link the molecules into chains along the a axis (Fig. 2). The packing is further stabilized by π-π interactions involving the C1—C6 benzene rings: Cg3···Cg3iv = 3.632 Å [symmetry code: (iv) 2 − x, −y, −1 − z, Cg3 is the centroid of th benzene ring].