Experimental. Crystal data

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1 organic compounds Acta Crystallographica Section E Structure Reports Online ISSN Bromo-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-(4-methoxybenzylideneamino)-1H-pyrazole-3-carbonitrile Guohui Zhu, Shuyan Li* and Zhiping Yang Department of Food and Biotechnology, Zhangzhou Vocational Technical College, Zhangzhou, People s Republic of China Correspondence lisy910@163.com Received 12 February 2008; accepted 27 February 2008 Key indicators: single-crystal X-ray study; T = 293 K; mean (C C) = Å; R factor = 0.050; wr factor = 0.161; data-to-parameter ratio = Experimental Crystal data C 19 H 10 BrCl 2 F 3 N 4 O M r = Monoclinic, P2 1 =c a = (7) Å b = (9) Å c = (11) Å = (13) Data collection Bruker P4/SMART CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2002) T min = 0.568, T max = Refinement R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections V = 2062 (2) Å 3 Z =4 Mo K radiation = 2.30 mm 1 T = 293 (2) K mm measured reflections 4681 independent reflections 4061 reflections with I > 2(I) R int = parameters H-atom parameters constrained max = 0.87 e Å 3 min = 1.22 e Å 3 The title compound, C 19 H 10 BrCl 2 F 3 N 4 O, 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. Related literature For the insecticidal properties of similar compounds, see: Philippe (1997, 2000). For a related structure, see: Zhong et al. (2005). Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; 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. This work was supported by the National Natural Science Foundation of Fujian Province (No. B ). Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2465). References 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 Philippe, J. (2000). US Patent No Sheldrick, G. M. (2008). Acta Cryst. A64, Zhong, P., Yang, Z. & Shi, Q. (2005). Acta Cryst. E61, o786 o787. o646 Zhu et al. doi: /s

2 supporting information [doi: /s ] 4-Bromo-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-(4-methoxybenzylideneamino)-1H-pyrazole-3-carbonitrile Guohui Zhu, Shuyan Li and Zhiping Yang S1. Comment 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. S2. Experimental 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 K). S3. Refinement 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 U iso (H) = 1.2 eq (C) and 0.96 Å, U iso = 1.5U eq (C) for CH 3 atoms. The low U eq 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 CF 3 group using a disorder model were unsuccessful. sup-1

3 Figure 1 The molecular structure of (I) showing the atom numbering scheme and displacement ellipsoids at the 30% probability level. 4-Bromo-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-(4- methoxybenzylideneamino)-1h-pyrazole-3- carbonitrile Crystal data C 19 H 10 BrCl 2 F 3 N 4 O M r = Monoclinic, P2 1 /c Hall symbol: -P 2ybc a = (7) Å b = (9) Å c = (11) Å β = (13) V = 2062 (2) Å 3 Z = 4 F(000) = 1024 D x = Mg m 3 Melting point = K Mo Kα radiation, λ = Å Cell parameters from 3780 reflections θ = µ = 2.30 mm 1 T = 293 K Block, colorless mm sup-2

4 Data collection Bruker P4 CCD diffractometer Radiation source: fine-focus sealed tube Graphite monochromator ω scans Absorption correction: multi-scan (SADABS; Bruker, 2002) T min = 0.568, T max = Refinement Refinement on F 2 Least-squares matrix: full R[F 2 > 2σ(F 2 )] = wr(f 2 ) = S = reflections 271 parameters 0 restraints Primary atom site location: structure-invariant direct methods measured reflections 4681 independent reflections 4061 reflections with I > 2σ(I) R int = θ max = 27.6, θ min = 2.8 h = k = l = Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained w = 1/[σ 2 (F o2 ) + (0.1058P) P] where P = (F o 2 + 2F c2 )/3 (Δ/σ) max = Δρ max = 0.87 e Å 3 Δρ min = 1.22 e Å 3 Special details 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 F 2 against ALL reflections. The weighted R-factor wr and goodness of fit S are based on F 2, conventional R-factors R are based on F, with F set to zero for negative F 2. The threshold expression of F 2 > σ(f 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R- factors based on All data will be even larger. Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 ) x y z U iso */U eq Br (4) (2) (3) (17) Cl (9) (7) (6) (3) Cl (9) (6) (5) (2) O (3) (2) (2) (7) N (3) (3) (3) (9) N (2) (18) (16) (5) N (2) (16) (15) (5) N (2) (17) (16) (5) C (3) (2) (18) (6) C (3) (19) (2) (6) C (3) (18) (18) (5) C (3) (2) (2) (7) C (3) (18) (17) (5) C (3) (2) (18) (5) C (3) (19) (2) (6) H * sup-3

5 C (3) (2) (2) (6) C (3) (2) (2) (6) H * C (3) (2) (18) (5) C (4) (2) (3) (8) C (3) (2) (2) (6) H * C (3) (2) (19) (6) C (3) (2) (2) (7) H * C (3) (2) (2) (6) H * C (3) (2) (2) (6) C (3) (3) (2) (7) H * C (3) (2) (2) (7) H * C (5) (3) (4) (15) H19C * H19B * H19A * F (3) (16) (2) (10) F (3) (2) (3) (11) F (4) (3) (2) (15) Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 Br (3) (2) (3) (12) (19) (13) Cl (5) (5) (4) (4) (4) (3) Cl (5) (5) (4) (4) (4) (3) O (15) (15) (18) (12) (13) (13) N (19) (19) (2) (15) (17) (16) N (13) (12) (11) (10) (10) (9) N (12) (10) (10) (9) (9) (8) N (13) (11) (12) (9) (10) (9) C (14) (13) (13) (10) (11) (10) C (15) (12) (14) (10) (11) (10) C (13) (11) (13) (10) (10) (9) C (17) (15) (16) (12) (13) (12) C (13) (11) (12) (9) (10) (9) C (14) (12) (13) (10) (11) (10) C (14) (13) (17) (10) (12) (11) C (14) (12) (16) (10) (12) (11) C (16) (13) (14) (12) (12) (11) C (14) (13) (13) (10) (10) (10) C (19) (16) (2) (14) (16) (15) C (16) (13) (15) (11) (12) (11) sup-4

6 C (15) (12) (13) (11) (11) (10) C (17) (13) (17) (12) (13) (12) C (17) (12) (16) (11) (13) (11) C (16) (16) (15) (11) (12) (11) C (17) (17) (19) (13) (14) (14) C (17) (13) (16) (12) (13) (11) C (3) (2) (4) (2) (3) (2) F (18) (11) (3) (11) (18) (14) F (16) (18) (3) (14) (18) (19) F (4) (2) (18) (2) (2) (16) Geometric parameters (Å, º) Br1 C (3) C8 C (4) Cl1 C (3) C9 C (4) Cl2 C (3) C9 H O1 C (4) C11 F (5) O1 C (5) C11 F (5) N1 C (5) C11 F (4) N2 C (4) C12 C (4) N2 N (3) C12 H N3 C (3) C13 C (4) N3 C (3) C13 C (4) N4 C (4) C14 C (4) N4 C (4) C14 H C1 C (4) C15 C (5) C1 C (4) C15 H C2 C (4) C16 C (5) C5 C (4) C17 C (5) C5 C (4) C17 H C6 C (4) C18 H C7 C (5) C19 H19C C7 H C19 H19B C8 C (4) C19 H19A C16 O1 C (3) F3 C11 F (3) C1 N2 N (2) F3 C11 F (4) N2 N3 C (2) F2 C11 F (3) N2 N3 C (2) F3 C11 C (3) C3 N3 C (2) F2 C11 C (3) C12 N4 C (3) F1 C11 C (3) N2 C1 C (2) N4 C12 C (3) N2 C1 C (3) N4 C12 H C2 C1 C (3) C13 C12 H C3 C2 C (2) C18 C13 C (3) C3 C2 Br (2) C18 C13 C (3) C1 C2 Br (2) C14 C13 C (3) N3 C3 N (2) C15 C14 C (3) sup-5

7 N3 C3 C (2) C15 C14 H N4 C3 C (2) C13 C14 H N1 C4 C (5) C16 C15 C (3) C6 C5 C (2) C16 C15 H C6 C5 N (2) C14 C15 H C10 C5 N (2) O1 C16 C (3) C5 C6 C (3) O1 C16 C (3) C5 C6 Cl (2) C15 C16 C (3) C7 C6 Cl (2) C18 C17 C (3) C8 C7 C (3) C18 C17 H C8 C7 H C16 C17 H C6 C7 H C17 C18 C (3) C7 C8 C (3) C17 C18 H C7 C8 C (3) C13 C18 H C9 C8 C (3) O1 C19 H19C C8 C9 C (3) O1 C19 H19B C8 C9 H H19C C19 H19B C10 C9 H O1 C19 H19A C9 C10 C (2) H19C C19 H19A C9 C10 Cl (2) H19B C19 H19A C5 C10 Cl (2) sup-6