(4-Bromo-3,5-dimethyl-1H-pyrazol-1-yl)(2,6-difluoro­phen­yl)methanone

Mei, X.-D.; Liang, Y.-H.; Wang, Z.-Y.

doi:10.1107/S1600536809052532

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o115

doi:10.1107/S1600536809052532

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(4-Bromo-3,5-dimethyl-1H-pyrazol-1-yl)(2,6-difluorophenyl)methanone

Xiang-Dong Mei,^a Yan-Hui Liang ^a and Zhong-Yue Wang ^a ^*

^aKey Laboratory of Pesticide Chemistry and Applications, Ministry of Agriculture, Institute of Plant Protection, Chinese Academy of Agricultural Sciences, Beijing 100193, People's Republic of China
^*Correspondence e-mail: wangzhy0301@sina.com

(Received 27 November 2009; accepted 7 December 2009; online 12 December 2009)

There are two molecules in the asymmetric unit of the title compound, C₁₂H₉BrF₂N₂O. They have very similar conformations: the dihedral angles between their pyrazole and benzene ring systems are 78.4 (3) and 78.6 (4)°. In the crystal, weak aromatic π–π stacking [centroid–centroid separation = 3.696 (5) Å] helps to establish the packing.

Related literature

For background to pyrazole derivatives in agrochemical and medicinal research, see: Sabbagh et al. (2009 ); Zheng et al. (2009 ).

Experimental

Crystal data

C₁₂H₉BrF₂N₂O
M_r = 315.12
Monoclinic, P 2₁ /c
a = 7.116 (3) Å
b = 29.304 (10) Å
c = 11.674 (4) Å
β = 91.533 (5)°
V = 2433.5 (15) Å³
Z = 8
Mo Kα radiation
μ = 3.39 mm⁻¹
T = 173 K
0.17 × 0.17 × 0.17 mm

Data collection

Rigaku Saturn724+ CCD diffractometer
Absorption correction: numerical (CrystalClear; Rigaku, 2008 ) T_min = 0.596, T_max = 0.596
15188 measured reflections
4276 independent reflections
3819 reflections with I > 2σ(I)
R_int = 0.060

Refinement

R[F² > 2σ(F²)] = 0.077
wR(F²) = 0.158
S = 1.27
4276 reflections
329 parameters
H-atom parameters constrained
Δρ_max = 1.08 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809052532/hb5260sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809052532/hb5260Isup2.hkl

checkCIF report

Related literature top

For background to pyrazole derivatives in agrochemical and medicinal research, see: Sabbagh et al. (2009); Zheng et al. (2009).

Experimental top

The title compound (0.2 g) was dissolved in ethanol (50 ml) at room temperature. Colourless crystals of compound (I) were obtained through slow evaporation after two weeks.

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELX97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound showing 50% probability displacement ellipsoids and atom-numbering scheme.

(4-Bromo-3,5-dimethyl-1H-pyrazol-1-yl)(2,6-difluorophenyl)methanone top

Crystal data top

C₁₂H₉BrF₂N₂O	F(000) = 1248
M_r = 315.12	D_x = 1.720 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 768 reflections
a = 7.116 (3) Å	θ = 2.2–27.5°
b = 29.304 (10) Å	µ = 3.39 mm⁻¹
c = 11.674 (4) Å	T = 173 K
β = 91.533 (5)°	Block, colourless
V = 2433.5 (15) Å³	0.17 × 0.17 × 0.17 mm
Z = 8

Data collection top

Rigaku Saturn724+ CCD diffractometer	4276 independent reflections
Radiation source: sealed tube	3819 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.060
ω scans at fixed χ = 45°	θ_max = 25.0°, θ_min = 2.8°
Absorption correction: numerical (CrystalClear; Rigaku, 2008)	h = −6→8
T_min = 0.596, T_max = 0.596	k = −34→34
15188 measured reflections	l = −12→13

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.158	H-atom parameters constrained
S = 1.27	w = 1/[σ²(F_o²) + (0.0402P)² + 7.5951P] where P = (F_o² + 2F_c²)/3
4276 reflections	(Δ/σ)_max < 0.001
329 parameters	Δρ_max = 1.08 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₁₂H₉BrF₂N₂O	V = 2433.5 (15) Å³
M_r = 315.12	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.116 (3) Å	µ = 3.39 mm⁻¹
b = 29.304 (10) Å	T = 173 K
c = 11.674 (4) Å	0.17 × 0.17 × 0.17 mm
β = 91.533 (5)°

Data collection top

Rigaku Saturn724+ CCD diffractometer	4276 independent reflections
Absorption correction: numerical (CrystalClear; Rigaku, 2008)	3819 reflections with I > 2σ(I)
T_min = 0.596, T_max = 0.596	R_int = 0.060
15188 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.077	0 restraints
wR(F²) = 0.158	H-atom parameters constrained
S = 1.27	Δρ_max = 1.08 e Å⁻³
4276 reflections	Δρ_min = −0.47 e Å⁻³
329 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Br1	0.48772 (10)	0.41014 (2)	0.89703 (6)	0.0409 (2)
Br2	1.00200 (10)	0.31950 (3)	1.09739 (6)	0.0491 (3)
F1	0.7911 (6)	0.30667 (16)	1.4485 (4)	0.0586 (12)
F2	0.1573 (5)	0.32948 (15)	1.3484 (3)	0.0503 (11)
F3	0.6692 (7)	0.42324 (19)	0.6390 (5)	0.0780 (16)
F4	1.3057 (7)	0.4580 (2)	0.6345 (6)	0.0889 (18)
O1	0.5532 (8)	0.26916 (16)	1.2410 (4)	0.0534 (14)
O2	1.0003 (10)	0.48031 (17)	0.8138 (4)	0.0649 (17)
N1	0.5031 (7)	0.34346 (17)	1.1966 (4)	0.0298 (12)
N2	0.4946 (7)	0.38788 (17)	1.2406 (5)	0.0322 (12)
N3	0.9873 (7)	0.40262 (16)	0.8255 (4)	0.0290 (12)
N4	0.9923 (7)	0.36189 (17)	0.7664 (4)	0.0303 (12)
C1	0.4918 (9)	0.4144 (2)	1.1501 (6)	0.0323 (15)
C2	0.4947 (9)	0.3874 (2)	1.0474 (5)	0.0304 (14)
C3	0.5023 (8)	0.3431 (2)	1.0775 (5)	0.0287 (14)
C4	0.4855 (11)	0.4650 (2)	1.1623 (6)	0.0431 (17)
H4A	0.4898	0.4731	1.2438	0.065*
H4B	0.3690	0.4767	1.1265	0.065*
H4C	0.5936	0.4785	1.1247	0.065*
C5	0.5039 (10)	0.3009 (2)	1.0060 (6)	0.0380 (16)
H5A	0.4885	0.3092	0.9250	0.057*
H5B	0.4005	0.2809	1.0279	0.057*
H5C	0.6238	0.2850	1.0183	0.057*
C6	0.5157 (10)	0.3064 (2)	1.2725 (5)	0.0351 (15)
C7	0.4758 (9)	0.3177 (2)	1.3954 (5)	0.0302 (14)
C8	0.6131 (9)	0.3157 (2)	1.4813 (6)	0.0362 (16)
C9	0.5761 (11)	0.3226 (2)	1.5946 (6)	0.0434 (18)
H9A	0.6742	0.3219	1.6513	0.052*
C10	0.3931 (10)	0.3306 (2)	1.6239 (6)	0.0387 (16)
H10A	0.3650	0.3341	1.7025	0.046*
C11	0.2501 (10)	0.3337 (2)	1.5433 (6)	0.0409 (17)
H11A	0.1250	0.3405	1.5642	0.049*
C12	0.2950 (9)	0.3266 (2)	1.4315 (6)	0.0355 (15)
C13	0.9966 (9)	0.3303 (2)	0.8459 (6)	0.0330 (15)
C14	0.9948 (9)	0.3504 (2)	0.9562 (5)	0.0325 (15)
C15	0.9901 (9)	0.3960 (2)	0.9434 (5)	0.0339 (15)
C16	1.0047 (12)	0.2810 (2)	0.8158 (7)	0.051 (2)
H16A	1.0217	0.2777	0.7332	0.076*
H16B	0.8872	0.2661	0.8369	0.076*
H16C	1.1105	0.2666	0.8575	0.076*
C17	0.9875 (11)	0.4331 (3)	1.0304 (6)	0.0481 (19)
H17A	0.9903	0.4197	1.1074	0.072*
H17B	0.8729	0.4512	1.0195	0.072*
H17C	1.0977	0.4527	1.0217	0.072*
C18	0.9919 (10)	0.4439 (2)	0.7649 (6)	0.0378 (16)
C19	0.9876 (10)	0.4396 (2)	0.6374 (6)	0.0374 (16)
C20	0.8243 (12)	0.4300 (3)	0.5776 (7)	0.052 (2)
C21	0.8162 (19)	0.4272 (3)	0.4604 (8)	0.087 (4)
H21A	0.7018	0.4200	0.4206	0.105*
C22	0.975 (2)	0.4350 (3)	0.4030 (8)	0.100 (5)
H22A	0.9711	0.4331	0.3217	0.120*
C23	1.141 (2)	0.4456 (4)	0.4571 (10)	0.090 (4)
H23A	1.2508	0.4512	0.4148	0.108*
C24	1.1454 (13)	0.4478 (3)	0.5754 (7)	0.058 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0507 (5)	0.0423 (4)	0.0296 (4)	−0.0035 (3)	0.0003 (3)	0.0051 (3)
Br2	0.0450 (4)	0.0693 (6)	0.0328 (4)	−0.0021 (4)	−0.0021 (3)	0.0171 (4)
F1	0.036 (2)	0.073 (3)	0.067 (3)	0.004 (2)	0.001 (2)	−0.013 (2)
F2	0.039 (2)	0.071 (3)	0.041 (2)	0.006 (2)	−0.0080 (19)	−0.004 (2)
F3	0.055 (3)	0.076 (4)	0.102 (4)	−0.014 (3)	−0.013 (3)	0.008 (3)
F4	0.049 (3)	0.093 (4)	0.126 (5)	−0.006 (3)	0.018 (3)	−0.001 (4)
O1	0.095 (4)	0.021 (2)	0.044 (3)	0.013 (3)	0.016 (3)	0.000 (2)
O2	0.124 (5)	0.029 (3)	0.042 (3)	0.000 (3)	0.002 (3)	−0.002 (2)
N1	0.036 (3)	0.027 (3)	0.026 (3)	−0.002 (2)	0.001 (2)	−0.003 (2)
N2	0.040 (3)	0.024 (3)	0.033 (3)	0.000 (2)	0.002 (2)	0.000 (2)
N3	0.037 (3)	0.023 (3)	0.027 (3)	0.001 (2)	0.000 (2)	−0.003 (2)
N4	0.039 (3)	0.025 (3)	0.027 (3)	−0.003 (2)	0.001 (2)	−0.005 (2)
C1	0.039 (4)	0.025 (3)	0.033 (4)	−0.001 (3)	0.004 (3)	0.000 (3)
C2	0.040 (4)	0.028 (3)	0.024 (3)	0.001 (3)	0.007 (3)	0.001 (3)
C3	0.029 (3)	0.028 (3)	0.029 (3)	−0.001 (3)	0.004 (3)	−0.002 (3)
C4	0.058 (5)	0.027 (4)	0.044 (4)	−0.007 (3)	−0.001 (4)	0.000 (3)
C5	0.047 (4)	0.035 (4)	0.032 (4)	−0.005 (3)	0.001 (3)	−0.006 (3)
C6	0.044 (4)	0.035 (4)	0.027 (4)	0.002 (3)	0.004 (3)	0.002 (3)
C7	0.041 (4)	0.020 (3)	0.030 (4)	0.000 (3)	0.002 (3)	0.000 (3)
C8	0.034 (4)	0.027 (3)	0.047 (4)	0.002 (3)	0.001 (3)	−0.004 (3)
C9	0.056 (5)	0.043 (4)	0.031 (4)	−0.006 (3)	−0.011 (3)	0.000 (3)
C10	0.053 (5)	0.029 (4)	0.033 (4)	0.002 (3)	−0.004 (3)	0.005 (3)
C11	0.038 (4)	0.040 (4)	0.045 (4)	−0.001 (3)	0.010 (3)	0.000 (3)
C12	0.036 (4)	0.037 (4)	0.034 (4)	−0.003 (3)	−0.001 (3)	−0.007 (3)
C13	0.036 (4)	0.025 (3)	0.038 (4)	−0.003 (3)	−0.002 (3)	0.000 (3)
C14	0.033 (4)	0.034 (4)	0.030 (4)	−0.003 (3)	0.001 (3)	0.002 (3)
C15	0.040 (4)	0.040 (4)	0.022 (3)	0.004 (3)	0.000 (3)	−0.004 (3)
C16	0.072 (5)	0.032 (4)	0.048 (5)	−0.010 (4)	0.002 (4)	0.005 (3)
C17	0.063 (5)	0.051 (5)	0.030 (4)	0.002 (4)	0.004 (4)	−0.014 (3)
C18	0.053 (4)	0.027 (4)	0.034 (4)	0.009 (3)	0.003 (3)	−0.004 (3)
C19	0.055 (4)	0.021 (3)	0.036 (4)	0.006 (3)	−0.002 (3)	0.003 (3)
C20	0.067 (6)	0.037 (4)	0.052 (5)	−0.003 (4)	−0.008 (4)	0.008 (4)
C21	0.167 (12)	0.046 (5)	0.047 (6)	−0.006 (6)	−0.051 (7)	0.008 (4)
C22	0.231 (18)	0.044 (6)	0.025 (5)	0.015 (8)	0.011 (8)	0.012 (4)
C23	0.147 (12)	0.062 (7)	0.065 (7)	0.016 (7)	0.052 (7)	0.016 (6)
C24	0.072 (6)	0.048 (5)	0.055 (5)	0.000 (4)	0.013 (5)	0.003 (4)

Geometric parameters (Å, º) top

Br1—C2	1.877 (6)	C7—C12	1.389 (9)
Br2—C14	1.881 (6)	C8—C9	1.371 (10)
F1—C8	1.358 (8)	C9—C10	1.375 (10)
F2—C12	1.363 (8)	C9—H9A	0.9500
F3—C20	1.347 (9)	C10—C11	1.370 (10)
F4—C24	1.351 (10)	C10—H10A	0.9500
O1—C6	1.185 (8)	C11—C12	1.368 (9)
O2—C18	1.210 (8)	C11—H11A	0.9500
N1—C3	1.390 (8)	C13—C14	1.416 (9)
N1—N2	1.401 (7)	C13—C16	1.489 (9)
N1—C6	1.403 (8)	C14—C15	1.345 (9)
N2—C1	1.311 (8)	C15—C17	1.487 (9)
N3—N4	1.380 (7)	C16—H16A	0.9800
N3—C15	1.390 (8)	C16—H16B	0.9800
N3—C18	1.403 (8)	C16—H16C	0.9800
N4—C13	1.311 (8)	C17—H17A	0.9800
C1—C2	1.438 (9)	C17—H17B	0.9800
C1—C4	1.491 (8)	C17—H17C	0.9800
C2—C3	1.346 (9)	C18—C19	1.494 (9)
C3—C5	1.491 (8)	C19—C20	1.369 (10)
C4—H4A	0.9800	C19—C24	1.373 (11)
C4—H4B	0.9800	C20—C21	1.371 (12)
C4—H4C	0.9800	C21—C22	1.350 (16)
C5—H5A	0.9800	C21—H21A	0.9500
C5—H5B	0.9800	C22—C23	1.358 (17)
C5—H5C	0.9800	C22—H22A	0.9500
C6—C7	1.506 (8)	C23—C24	1.382 (13)
C7—C8	1.382 (9)	C23—H23A	0.9500

C3—N1—N2	112.0 (5)	C10—C11—H11A	121.4
C3—N1—C6	128.7 (5)	F2—C12—C11	119.2 (6)
N2—N1—C6	119.3 (5)	F2—C12—C7	116.7 (6)
C1—N2—N1	104.8 (5)	C11—C12—C7	124.1 (6)
N4—N3—C15	112.0 (5)	N4—C13—C14	110.5 (5)
N4—N3—C18	119.5 (5)	N4—C13—C16	121.2 (6)
C15—N3—C18	128.3 (5)	C14—C13—C16	128.3 (6)
C13—N4—N3	104.9 (5)	C15—C14—C13	108.3 (6)
N2—C1—C2	110.2 (5)	C15—C14—Br2	125.1 (5)
N2—C1—C4	120.9 (6)	C13—C14—Br2	126.6 (5)
C2—C1—C4	128.9 (6)	C14—C15—N3	104.4 (5)
C3—C2—C1	108.3 (5)	C14—C15—C17	130.6 (6)
C3—C2—Br1	125.9 (5)	N3—C15—C17	125.1 (6)
C1—C2—Br1	125.7 (5)	C13—C16—H16A	109.5
C2—C3—N1	104.7 (5)	C13—C16—H16B	109.5
C2—C3—C5	130.8 (6)	H16A—C16—H16B	109.5
N1—C3—C5	124.5 (6)	C13—C16—H16C	109.5
C1—C4—H4A	109.5	H16A—C16—H16C	109.5
C1—C4—H4B	109.5	H16B—C16—H16C	109.5
H4A—C4—H4B	109.5	C15—C17—H17A	109.5
C1—C4—H4C	109.5	C15—C17—H17B	109.5
H4A—C4—H4C	109.5	H17A—C17—H17B	109.5
H4B—C4—H4C	109.5	C15—C17—H17C	109.5
C3—C5—H5A	109.5	H17A—C17—H17C	109.5
C3—C5—H5B	109.5	H17B—C17—H17C	109.5
H5A—C5—H5B	109.5	O2—C18—N3	121.6 (6)
C3—C5—H5C	109.5	O2—C18—C19	123.0 (6)
H5A—C5—H5C	109.5	N3—C18—C19	115.4 (5)
H5B—C5—H5C	109.5	C20—C19—C24	117.6 (7)
O1—C6—N1	121.9 (6)	C20—C19—C18	121.3 (7)
O1—C6—C7	123.2 (6)	C24—C19—C18	121.0 (7)
N1—C6—C7	114.9 (5)	F3—C20—C19	117.2 (7)
C8—C7—C12	115.5 (6)	F3—C20—C21	120.6 (9)
C8—C7—C6	122.2 (6)	C19—C20—C21	122.2 (9)
C12—C7—C6	122.0 (6)	C22—C21—C20	118.1 (10)
F1—C8—C9	120.4 (6)	C22—C21—H21A	120.9
F1—C8—C7	116.8 (6)	C20—C21—H21A	120.9
C9—C8—C7	122.9 (6)	C21—C22—C23	122.5 (10)
C8—C9—C10	118.3 (7)	C21—C22—H22A	118.8
C8—C9—H9A	120.9	C23—C22—H22A	118.8
C10—C9—H9A	120.9	C22—C23—C24	118.1 (11)
C11—C10—C9	122.1 (7)	C22—C23—H23A	120.9
C11—C10—H10A	119.0	C24—C23—H23A	120.9
C9—C10—H10A	119.0	F4—C24—C19	117.4 (8)
C12—C11—C10	117.2 (7)	F4—C24—C23	121.2 (9)
C12—C11—H11A	121.4	C19—C24—C23	121.4 (10)

C3—N1—N2—C1	−1.0 (7)	C8—C7—C12—C11	1.0 (10)
C6—N1—N2—C1	177.4 (6)	C6—C7—C12—C11	175.0 (6)
C15—N3—N4—C13	0.5 (7)	N3—N4—C13—C14	−0.1 (7)
C18—N3—N4—C13	176.6 (6)	N3—N4—C13—C16	−179.4 (6)
N1—N2—C1—C2	1.1 (7)	N4—C13—C14—C15	−0.3 (8)
N1—N2—C1—C4	−179.2 (6)	C16—C13—C14—C15	178.9 (7)
N2—C1—C2—C3	−0.9 (8)	N4—C13—C14—Br2	−179.3 (5)
C4—C1—C2—C3	179.4 (7)	C16—C13—C14—Br2	−0.1 (11)
N2—C1—C2—Br1	178.8 (5)	C13—C14—C15—N3	0.6 (7)
C4—C1—C2—Br1	−0.9 (11)	Br2—C14—C15—N3	179.6 (4)
C1—C2—C3—N1	0.3 (7)	C13—C14—C15—C17	−179.6 (7)
Br1—C2—C3—N1	−179.4 (4)	Br2—C14—C15—C17	−0.6 (11)
C1—C2—C3—C5	178.5 (6)	N4—N3—C15—C14	−0.7 (7)
Br1—C2—C3—C5	−1.2 (11)	C18—N3—C15—C14	−176.4 (6)
N2—N1—C3—C2	0.4 (7)	N4—N3—C15—C17	179.5 (6)
C6—N1—C3—C2	−177.8 (6)	C18—N3—C15—C17	3.8 (11)
N2—N1—C3—C5	−177.9 (6)	N4—N3—C18—O2	−175.1 (7)
C6—N1—C3—C5	3.8 (10)	C15—N3—C18—O2	0.3 (11)
C3—N1—C6—O1	10.4 (11)	N4—N3—C18—C19	4.4 (9)
N2—N1—C6—O1	−167.7 (6)	C15—N3—C18—C19	179.8 (6)
C3—N1—C6—C7	−168.9 (6)	O2—C18—C19—C20	−103.7 (9)
N2—N1—C6—C7	13.0 (8)	N3—C18—C19—C20	76.9 (8)
O1—C6—C7—C8	67.7 (10)	O2—C18—C19—C24	72.5 (10)
N1—C6—C7—C8	−113.0 (7)	N3—C18—C19—C24	−107.0 (8)
O1—C6—C7—C12	−105.9 (8)	C24—C19—C20—F3	−178.2 (7)
N1—C6—C7—C12	73.4 (8)	C18—C19—C20—F3	−2.0 (10)
C12—C7—C8—F1	179.5 (6)	C24—C19—C20—C21	1.8 (11)
C6—C7—C8—F1	5.5 (9)	C18—C19—C20—C21	178.1 (7)
C12—C7—C8—C9	−1.1 (9)	F3—C20—C21—C22	179.0 (8)
C6—C7—C8—C9	−175.1 (6)	C19—C20—C21—C22	−1.1 (13)
F1—C8—C9—C10	−178.6 (6)	C20—C21—C22—C23	−0.2 (16)
C7—C8—C9—C10	2.0 (10)	C21—C22—C23—C24	0.6 (16)
C8—C9—C10—C11	−2.8 (10)	C20—C19—C24—F4	179.0 (7)
C9—C10—C11—C12	2.6 (10)	C18—C19—C24—F4	2.7 (11)
C10—C11—C12—F2	−179.8 (6)	C20—C19—C24—C23	−1.3 (12)
C10—C11—C12—C7	−1.7 (10)	C18—C19—C24—C23	−177.6 (8)
C8—C7—C12—F2	179.0 (6)	C22—C23—C24—F4	179.9 (9)
C6—C7—C12—F2	−7.0 (9)	C22—C23—C24—C19	0.2 (14)

Experimental details

Crystal data
Chemical formula	C₁₂H₉BrF₂N₂O
M_r	315.12
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	7.116 (3), 29.304 (10), 11.674 (4)
β (°)	91.533 (5)
V (Å³)	2433.5 (15)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	3.39
Crystal size (mm)	0.17 × 0.17 × 0.17

Data collection
Diffractometer	Rigaku Saturn724+ CCD diffractometer
Absorption correction	Numerical (CrystalClear; Rigaku, 2008)
T_min, T_max	0.596, 0.596
No. of measured, independent and observed [I > 2σ(I)] reflections	15188, 4276, 3819
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.077, 0.158, 1.27
No. of reflections	4276
No. of parameters	329
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.08, −0.47

Computer programs: CrystalClear (Rigaku, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELX97 (Sheldrick, 2008).

Acknowledgements

This work was supported by National Technology System for the Grape Industry, the Major State Basic Research Development Program of China (No. 2006CB101907 and No. 2010CB126106), and the 863 high-tech key project of China (2006AA10A203).

References

Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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