Acta Cryst. (2008). E64, o646 [ doi:10.1107/S1600536808005539 ]
The title compound, C19H10BrCl2F3N4O, is an imine with an overall Y shape. The dihedral angles between the pyrazole ring and the methoxy- and trifluoromethyl-substituted benzene ring planes are 88.4 (2) and 65.8 (2)°, respectively.
The title compound was prepared by literature methods (Zhong et al., 2005, Philippe, 2000). Colourless single crystals suitable for X-ray analysis were obtained by slow evaporation of an anhydrous ethanol-acetone (2:1) solution of (I) (m.p. 435–437 K).
All H atoms were initially located in a difference Fourier map but were eventually placed in their geometrically idealized positions and constrained to ride on their parent atoms, with C—H = 0.93 Å, and with Uiso(H) = 1.2eq(C) and 0.96 Å, Uiso = 1.5Ueq (C) for CH3 atoms. The low Ueq of C11 as compared to its neighbours may be attributed to the high displacement parameters for atoms F1, F2 and F3, indicating either large thermal motion or rotational disorder of the trifluoromethyl group. However, attempts to represent the CF3 group using a disorder model were unsuccessful.
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
![[Figure 1]](./sj2465fig1thm.gif)
| Fig. 1. The molecular structure of (I) showing the atom numbering scheme and displacement ellipsoids at the 30% probability level. |
| C19H10BrCl2F3N4O | F000 = 1024 |
| Mr = 518.12 | Dx = 1.669 Mg m−3 |
| Monoclinic, P21/c | Melting point = 435–437 K |
| Hall symbol: -P 2ybc | Mo Kα radiation λ = 0.71073 Å |
| a = 10.215 (7) Å | Cell parameters from 3780 reflections |
| b = 13.407 (9) Å | θ = 2.6–24.2º |
| c = 15.108 (11) Å | µ = 2.30 mm−1 |
| β = 94.634 (13)º | T = 293 (2) K |
| V = 2062 (2) Å3 | Block, colorless |
| Z = 4 | 0.28 × 0.25 × 0.23 mm |
| Bruker P4 CCD diffractometer | 4681 independent reflections |
| Radiation source: fine-focus sealed tube | 4061 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.028 |
| T = 293(2) K | θmax = 27.6º |
| ω scans | θmin = 2.8º |
| Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −13→10 |
| Tmin = 0.568, Tmax = 0.618 | k = −17→17 |
| 15375 measured reflections | l = −19→19 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.049 | H-atom parameters constrained |
| wR(F2) = 0.160 | w = 1/[σ2(Fo2) + (0.1058P)2 + 1.2139P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.02 | (Δ/σ)max = 0.001 |
| 4681 reflections | Δρmax = 0.87 e Å−3 |
| 271 parameters | Δρmin = −1.22 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
| C19H10BrCl2F3N4O | V = 2062 (2) Å3 |
| Mr = 518.12 | Z = 4 |
| Monoclinic, P21/c | Mo Kα |
| a = 10.215 (7) Å | µ = 2.30 mm−1 |
| b = 13.407 (9) Å | T = 293 (2) K |
| c = 15.108 (11) Å | 0.28 × 0.25 × 0.23 mm |
| β = 94.634 (13)º |
| Bruker P4 CCD diffractometer | 4681 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2002) | 4061 reflections with I > 2σ(I) |
| Tmin = 0.568, Tmax = 0.618 | Rint = 0.028 |
| 15375 measured reflections |
| R[F2 > 2σ(F2)] = 0.049 | 271 parameters |
| wR(F2) = 0.160 | H-atom parameters constrained |
| S = 1.02 | Δρmax = 0.87 e Å−3 |
| 4681 reflections | Δρmin = −1.22 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 > σ(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 | ||
| Br1 | 0.47949 (4) | 0.47599 (2) | 0.18806 (3) | 0.06204 (17) | |
| Cl1 | 0.47167 (9) | 0.15617 (7) | −0.07867 (6) | 0.0635 (3) | |
| Cl2 | 0.21780 (9) | 0.09133 (6) | 0.21206 (5) | 0.0598 (2) | |
| O1 | −0.1317 (3) | 0.5592 (2) | −0.2291 (2) | 0.0705 (7) | |
| N1 | 0.7437 (3) | 0.2820 (3) | 0.3107 (3) | 0.0722 (9) | |
| N2 | 0.5089 (2) | 0.17560 (18) | 0.16494 (16) | 0.0440 (5) | |
| N3 | 0.4063 (2) | 0.19538 (16) | 0.10558 (15) | 0.0401 (5) | |
| N4 | 0.2718 (2) | 0.32184 (17) | 0.03993 (16) | 0.0440 (5) | |
| C1 | 0.5457 (3) | 0.2656 (2) | 0.19544 (18) | 0.0426 (6) | |
| C2 | 0.4669 (3) | 0.34164 (19) | 0.1561 (2) | 0.0431 (6) | |
| C3 | 0.3773 (3) | 0.29447 (18) | 0.09722 (18) | 0.0393 (5) | |
| C4 | 0.6555 (3) | 0.2745 (2) | 0.2597 (2) | 0.0510 (7) | |
| C5 | 0.3380 (3) | 0.11449 (18) | 0.06234 (17) | 0.0372 (5) | |
| C6 | 0.2496 (3) | 0.0587 (2) | 0.10637 (18) | 0.0404 (5) | |
| C7 | 0.1868 (3) | −0.02304 (19) | 0.0660 (2) | 0.0455 (6) | |
| H7 | 0.1275 | −0.0603 | 0.0959 | 0.055* | |
| C8 | 0.2134 (3) | −0.0482 (2) | −0.0186 (2) | 0.0444 (6) | |
| C9 | 0.2998 (3) | 0.0065 (2) | −0.0649 (2) | 0.0467 (6) | |
| H9 | 0.3161 | −0.0110 | −0.1225 | 0.056* | |
| C10 | 0.3616 (3) | 0.0880 (2) | −0.02374 (18) | 0.0412 (5) | |
| C11 | 0.1513 (4) | −0.1404 (2) | −0.0601 (3) | 0.0606 (8) | |
| C12 | 0.2714 (3) | 0.4090 (2) | 0.0053 (2) | 0.0468 (6) | |
| H12 | 0.3433 | 0.4503 | 0.0194 | 0.056* | |
| C13 | 0.1648 (3) | 0.4469 (2) | −0.05455 (19) | 0.0423 (6) | |
| C14 | 0.1740 (3) | 0.5440 (2) | −0.0862 (2) | 0.0499 (7) | |
| H14 | 0.2473 | 0.5823 | −0.0682 | 0.060* | |
| C15 | 0.0759 (3) | 0.5846 (2) | −0.1438 (2) | 0.0485 (6) | |
| H15 | 0.0826 | 0.6499 | −0.1637 | 0.058* | |
| C16 | −0.0316 (3) | 0.5275 (2) | −0.1712 (2) | 0.0474 (6) | |
| C17 | −0.0425 (3) | 0.4296 (3) | −0.1403 (2) | 0.0556 (7) | |
| H17 | −0.1157 | 0.3913 | −0.1586 | 0.067* | |
| C18 | 0.0549 (3) | 0.3903 (2) | −0.0829 (2) | 0.0499 (7) | |
| H18 | 0.0476 | 0.3252 | −0.0627 | 0.060* | |
| C19 | −0.1250 (5) | 0.6581 (3) | −0.2612 (4) | 0.0878 (15) | |
| H19C | −0.2005 | 0.6714 | −0.3015 | 0.132* | |
| H19B | −0.0467 | 0.6660 | −0.2916 | 0.132* | |
| H19A | −0.1233 | 0.7039 | −0.2123 | 0.132* | |
| F1 | 0.2269 (3) | −0.21908 (16) | −0.0449 (2) | 0.0972 (10) | |
| F2 | 0.0391 (3) | −0.1633 (2) | −0.0287 (3) | 0.1064 (11) | |
| F3 | 0.1310 (4) | −0.1354 (3) | −0.1460 (2) | 0.1269 (15) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Br1 | 0.0722 (3) | 0.0340 (2) | 0.0776 (3) | −0.00455 (12) | −0.00746 (19) | −0.01343 (13) |
| Cl1 | 0.0740 (5) | 0.0690 (5) | 0.0497 (4) | −0.0276 (4) | 0.0184 (4) | −0.0037 (3) |
| Cl2 | 0.0782 (5) | 0.0583 (5) | 0.0453 (4) | 0.0063 (4) | 0.0197 (4) | 0.0037 (3) |
| O1 | 0.0646 (15) | 0.0602 (15) | 0.0822 (18) | 0.0061 (12) | −0.0225 (13) | 0.0004 (13) |
| N1 | 0.0669 (19) | 0.0670 (19) | 0.079 (2) | 0.0077 (15) | −0.0188 (17) | −0.0201 (16) |
| N2 | 0.0514 (13) | 0.0380 (12) | 0.0416 (11) | 0.0037 (10) | −0.0028 (10) | −0.0017 (9) |
| N3 | 0.0520 (12) | 0.0308 (10) | 0.0366 (10) | −0.0008 (9) | −0.0025 (9) | −0.0019 (8) |
| N4 | 0.0547 (13) | 0.0327 (11) | 0.0434 (12) | 0.0007 (9) | −0.0037 (10) | −0.0006 (9) |
| C1 | 0.0483 (14) | 0.0377 (13) | 0.0412 (13) | 0.0013 (10) | 0.0008 (11) | −0.0060 (10) |
| C2 | 0.0517 (15) | 0.0309 (12) | 0.0460 (14) | −0.0012 (10) | −0.0002 (11) | −0.0049 (10) |
| C3 | 0.0478 (13) | 0.0294 (11) | 0.0407 (13) | −0.0014 (10) | 0.0045 (10) | −0.0017 (9) |
| C4 | 0.0555 (17) | 0.0464 (15) | 0.0501 (16) | 0.0048 (12) | −0.0012 (13) | −0.0126 (12) |
| C5 | 0.0458 (13) | 0.0271 (11) | 0.0381 (12) | 0.0005 (9) | 0.0002 (10) | −0.0006 (9) |
| C6 | 0.0481 (14) | 0.0325 (12) | 0.0410 (13) | 0.0050 (10) | 0.0052 (11) | 0.0046 (10) |
| C7 | 0.0440 (14) | 0.0331 (13) | 0.0596 (17) | −0.0016 (10) | 0.0057 (12) | 0.0084 (11) |
| C8 | 0.0461 (14) | 0.0305 (12) | 0.0551 (16) | −0.0028 (10) | −0.0045 (12) | −0.0017 (11) |
| C9 | 0.0571 (16) | 0.0409 (13) | 0.0419 (14) | −0.0053 (12) | 0.0019 (12) | −0.0070 (11) |
| C10 | 0.0477 (14) | 0.0372 (13) | 0.0392 (13) | −0.0059 (10) | 0.0053 (10) | −0.0023 (10) |
| C11 | 0.0627 (19) | 0.0413 (16) | 0.075 (2) | −0.0116 (14) | −0.0131 (16) | −0.0049 (15) |
| C12 | 0.0539 (16) | 0.0358 (13) | 0.0498 (15) | −0.0028 (11) | −0.0012 (12) | 0.0000 (11) |
| C13 | 0.0527 (15) | 0.0331 (12) | 0.0407 (13) | −0.0004 (11) | 0.0027 (11) | −0.0002 (10) |
| C14 | 0.0570 (17) | 0.0344 (13) | 0.0567 (17) | −0.0059 (12) | −0.0056 (13) | 0.0023 (12) |
| C15 | 0.0604 (17) | 0.0320 (12) | 0.0522 (16) | 0.0032 (11) | −0.0007 (13) | 0.0019 (11) |
| C16 | 0.0513 (16) | 0.0440 (16) | 0.0461 (15) | 0.0069 (11) | −0.0005 (12) | −0.0038 (11) |
| C17 | 0.0546 (17) | 0.0481 (17) | 0.0628 (19) | −0.0122 (13) | −0.0031 (14) | −0.0011 (14) |
| C18 | 0.0614 (17) | 0.0363 (13) | 0.0522 (16) | −0.0082 (12) | 0.0061 (13) | 0.0024 (11) |
| C19 | 0.091 (3) | 0.059 (2) | 0.106 (4) | 0.020 (2) | −0.035 (3) | 0.006 (2) |
| F1 | 0.0977 (18) | 0.0389 (11) | 0.150 (3) | 0.0004 (11) | −0.0223 (18) | −0.0259 (14) |
| F2 | 0.0762 (16) | 0.0812 (18) | 0.164 (3) | −0.0395 (14) | 0.0210 (18) | −0.0324 (19) |
| F3 | 0.198 (4) | 0.095 (2) | 0.0784 (18) | −0.074 (2) | −0.044 (2) | −0.0037 (16) |
| Br1—C2 | 1.867 (3) | C8—C11 | 1.503 (4) |
| Cl1—C10 | 1.714 (3) | C9—C10 | 1.384 (4) |
| Cl2—C6 | 1.712 (3) | C9—H9 | 0.9300 |
| O1—C16 | 1.359 (4) | C11—F3 | 1.299 (5) |
| O1—C19 | 1.416 (5) | C11—F2 | 1.311 (5) |
| N1—C4 | 1.142 (5) | C11—F1 | 1.317 (4) |
| N2—C1 | 1.334 (4) | C12—C13 | 1.450 (4) |
| N2—N3 | 1.349 (3) | C12—H12 | 0.9300 |
| N3—C3 | 1.365 (3) | C13—C18 | 1.393 (4) |
| N3—C5 | 1.420 (3) | C13—C14 | 1.393 (4) |
| N4—C12 | 1.280 (4) | C14—C15 | 1.385 (4) |
| N4—C3 | 1.376 (4) | C14—H14 | 0.9300 |
| C1—C2 | 1.402 (4) | C15—C16 | 1.374 (5) |
| C1—C4 | 1.428 (4) | C15—H15 | 0.9300 |
| C2—C3 | 1.377 (4) | C16—C17 | 1.401 (5) |
| C5—C6 | 1.383 (4) | C17—C18 | 1.370 (5) |
| C5—C10 | 1.388 (4) | C17—H17 | 0.9300 |
| C6—C7 | 1.386 (4) | C18—H18 | 0.9300 |
| C7—C8 | 1.371 (5) | C19—H19C | 0.9600 |
| C7—H7 | 0.9300 | C19—H19B | 0.9600 |
| C8—C9 | 1.380 (4) | C19—H19A | 0.9600 |
| C16—O1—C19 | 117.3 (3) | F3—C11—F2 | 107.5 (3) |
| C1—N2—N3 | 103.5 (2) | F3—C11—F1 | 105.0 (4) |
| N2—N3—C3 | 113.8 (2) | F2—C11—F1 | 105.5 (3) |
| N2—N3—C5 | 118.8 (2) | F3—C11—C8 | 113.7 (3) |
| C3—N3—C5 | 127.3 (2) | F2—C11—C8 | 113.2 (3) |
| C12—N4—C3 | 118.5 (3) | F1—C11—C8 | 111.4 (3) |
| N2—C1—C2 | 112.0 (2) | N4—C12—C13 | 123.5 (3) |
| N2—C1—C4 | 119.7 (3) | N4—C12—H12 | 118.3 |
| C2—C1—C4 | 128.3 (3) | C13—C12—H12 | 118.3 |
| C3—C2—C1 | 105.6 (2) | C18—C13—C14 | 118.6 (3) |
| C3—C2—Br1 | 129.7 (2) | C18—C13—C12 | 123.2 (3) |
| C1—C2—Br1 | 124.6 (2) | C14—C13—C12 | 118.2 (3) |
| N3—C3—N4 | 118.1 (2) | C15—C14—C13 | 121.1 (3) |
| N3—C3—C2 | 105.0 (2) | C15—C14—H14 | 119.4 |
| N4—C3—C2 | 136.8 (2) | C13—C14—H14 | 119.4 |
| N1—C4—C1 | 179.6 (5) | C16—C15—C14 | 119.4 (3) |
| C6—C5—C10 | 118.8 (2) | C16—C15—H15 | 120.3 |
| C6—C5—N3 | 120.5 (2) | C14—C15—H15 | 120.3 |
| C10—C5—N3 | 120.7 (2) | O1—C16—C15 | 124.1 (3) |
| C5—C6—C7 | 120.8 (3) | O1—C16—C17 | 115.5 (3) |
| C5—C6—Cl2 | 119.4 (2) | C15—C16—C17 | 120.3 (3) |
| C7—C6—Cl2 | 119.8 (2) | C18—C17—C16 | 119.8 (3) |
| C8—C7—C6 | 119.1 (3) | C18—C17—H17 | 120.1 |
| C8—C7—H7 | 120.5 | C16—C17—H17 | 120.1 |
| C6—C7—H7 | 120.5 | C17—C18—C13 | 120.8 (3) |
| C7—C8—C9 | 121.6 (3) | C17—C18—H18 | 119.6 |
| C7—C8—C11 | 118.9 (3) | C13—C18—H18 | 119.6 |
| C9—C8—C11 | 119.5 (3) | O1—C19—H19C | 109.5 |
| C8—C9—C10 | 118.7 (3) | O1—C19—H19B | 109.5 |
| C8—C9—H9 | 120.7 | H19C—C19—H19B | 109.5 |
| C10—C9—H9 | 120.7 | O1—C19—H19A | 109.5 |
| C9—C10—C5 | 121.0 (2) | H19C—C19—H19A | 109.5 |
| C9—C10—Cl1 | 119.8 (2) | H19B—C19—H19A | 109.5 |
| C5—C10—Cl1 | 119.2 (2) |
This work was supported by the National Natural Science Foundation of Fujian Province (No. B0610033).
Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Winsonsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565–?.
Philippe, J. (1997). US Patent No. 6 001 384.
Philippe, J. (2000). US Patent No. 6 096 329.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Zhong, P., Yang, Z. & Shi, Q. (2005). Acta Cryst. E61, o786–o787.
The title compound, (I), (Fig. 1) is similar to the very effective insecticides used to treat animals such as cows and sheep (Philippe, 1997, 2000) and its structure is reported here, Fig 1. The molecule contains three essentially planar rings and the dihedral angles between the pyrazole ring (C1—C3, N2, N3) and the ring planes of the (C5—C7) and (C13—C17) benzene rings are 88.4 (2)° and 65.8 (2)°, respectively.