2-Bromo-2-(5-bromo-1H-1,2,4-triazol-1-yl)-1-(2,4-difluoro-phen-yl)ethanone.

In the title compound, C(10)H(5)Br(2)F(2)N(3)O, the mean planes of the benzene and triazole rings form a dihedral angle of 84.86 (2)°. In the crystal structure, weak inter-molecular C-H⋯O hydrogen bonds link mol-ecules into extended chains propagating along the c axis.

Related literature

For general properties of 1,2,4-triazole derivatives, see: Garfunkle et al. (2008 ▶); Yu et al. (2009 ▶). For their anti­microbial activity, see: Luo et al. (2009 ▶); Zhang et al. (2010 ▶).

Experimental

Crystal data

C10H5Br2F2N3O

M = 380.99

Monoclinic,

a = 9.273 (2) Å

b = 9.375 (2) Å

c = 14.982 (3) Å

β = 104.916 (3)°

V = 1258.5 (5) Å3

Z = 4

Mo Kα radiation

μ = 6.46 mm−1

T = 298 K

0.26 × 0.25 × 0.25 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.199, T max = 0.203

6096 measured reflections

2206 independent reflections

1577 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.100

S = 1.04

2206 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.61 e Å−3

Δρmin = −0.49 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; 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: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810011359/lh5016sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011359/lh5016Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H5Br2F2N3O	F(000) = 728
Mr = 380.99	Dx = 2.011 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1838 reflections
a = 9.273 (2) Å	θ = 2.3–22.5°
b = 9.375 (2) Å	µ = 6.46 mm−1
c = 14.982 (3) Å	T = 298 K
β = 104.916 (3)°	Block, colourless
V = 1258.5 (5) Å3	0.26 × 0.25 × 0.25 mm
Z = 4

Bruker SMART CCD diffractometer	2206 independent reflections
Radiation source: fine-focus sealed tube	1577 reflections with I > 2σ(I)
graphite	Rint = 0.036
φ and ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→11
Tmin = 0.199, Tmax = 0.203	k = −10→11
6096 measured reflections	l = −15→17

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0482P)2 + 0.5764P] where P = (Fo2 + 2Fc2)/3
2206 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.61 e Å−3
0 restraints	Δρmin = −0.49 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.88429 (6)	0.61973 (5)	0.21078 (5)	0.0741 (2)
Br2	0.65968 (6)	0.75021 (7)	0.40152 (3)	0.0777 (2)
C1	0.7324 (6)	1.0030 (5)	0.1617 (4)	0.0783 (17)
H1	0.7343	1.0949	0.1387	0.094*
C2	0.7921 (5)	0.7951 (5)	0.1945 (3)	0.0512 (11)
C3	0.5841 (4)	0.7348 (5)	0.2679 (3)	0.0426 (10)
H3	0.5927	0.6355	0.2496	0.051*
C4	0.4187 (5)	0.7796 (4)	0.2384 (3)	0.0426 (10)
C5	0.3310 (4)	0.7498 (4)	0.1425 (3)	0.0375 (9)
C6	0.3760 (5)	0.6720 (4)	0.0765 (3)	0.0424 (10)
C7	0.2865 (5)	0.6440 (5)	−0.0092 (3)	0.0502 (11)
H7	0.3205	0.5910	−0.0521	0.060*
C8	0.1455 (6)	0.6970 (5)	−0.0291 (3)	0.0576 (12)
C9	0.0924 (5)	0.7769 (6)	0.0313 (4)	0.0656 (14)
H9	−0.0044	0.8127	0.0152	0.079*
C10	0.1867 (5)	0.8030 (5)	0.1170 (3)	0.0553 (12)
H10	0.1525	0.8579	0.1591	0.066*
F1	0.5154 (3)	0.6180 (3)	0.09542 (17)	0.0645 (8)
F2	0.0553 (3)	0.6703 (4)	−0.11300 (19)	0.0911 (10)
N1	0.8368 (5)	0.9052 (4)	0.1564 (3)	0.0719 (13)
N2	0.6690 (4)	0.8238 (4)	0.2223 (2)	0.0450 (9)
N3	0.6279 (4)	0.9620 (4)	0.2011 (3)	0.0602 (10)
O1	0.3620 (4)	0.8357 (4)	0.2925 (2)	0.0640 (9)

	U11	U22	U33	U12	U13	U23
Br1	0.0500 (3)	0.0474 (3)	0.1299 (5)	0.0074 (2)	0.0324 (3)	−0.0047 (3)
Br2	0.0597 (4)	0.1177 (5)	0.0494 (3)	−0.0031 (3)	0.0025 (2)	−0.0060 (3)
C1	0.075 (4)	0.046 (3)	0.133 (5)	0.008 (3)	0.063 (4)	0.018 (3)
C2	0.039 (3)	0.041 (3)	0.075 (3)	−0.001 (2)	0.016 (2)	−0.010 (2)
C3	0.039 (2)	0.044 (2)	0.045 (2)	−0.0020 (19)	0.0114 (19)	−0.0029 (19)
C4	0.039 (2)	0.042 (2)	0.051 (2)	−0.0024 (19)	0.019 (2)	−0.0017 (19)
C5	0.034 (2)	0.038 (2)	0.044 (2)	−0.0016 (18)	0.0159 (17)	−0.0005 (18)
C6	0.034 (2)	0.047 (2)	0.049 (2)	0.012 (2)	0.016 (2)	0.004 (2)
C7	0.045 (3)	0.063 (3)	0.042 (2)	0.013 (2)	0.011 (2)	−0.003 (2)
C8	0.055 (3)	0.064 (3)	0.047 (3)	0.008 (3)	0.001 (2)	−0.003 (2)
C9	0.036 (3)	0.088 (4)	0.068 (3)	0.014 (3)	0.005 (2)	−0.013 (3)
C10	0.037 (3)	0.067 (3)	0.063 (3)	0.006 (2)	0.016 (2)	−0.020 (2)
F1	0.0477 (16)	0.085 (2)	0.0583 (16)	0.0246 (14)	0.0088 (12)	−0.0174 (14)
F2	0.067 (2)	0.136 (3)	0.0549 (17)	0.030 (2)	−0.0130 (15)	−0.0225 (18)
N1	0.065 (3)	0.048 (3)	0.120 (4)	0.000 (2)	0.056 (3)	0.006 (2)
N2	0.036 (2)	0.037 (2)	0.064 (2)	−0.0055 (16)	0.0180 (17)	−0.0069 (17)
N3	0.058 (3)	0.038 (2)	0.096 (3)	0.0038 (19)	0.039 (2)	0.006 (2)
O1	0.052 (2)	0.085 (2)	0.058 (2)	0.0053 (18)	0.0201 (16)	−0.0244 (18)

Br1—C2	1.840 (4)	C5—C6	1.378 (5)
Br2—C3	1.948 (4)	C5—C10	1.387 (6)
C1—N3	1.314 (6)	C6—F1	1.348 (4)
C1—N1	1.351 (6)	C6—C7	1.362 (6)
C1—H1	0.9300	C7—C8	1.358 (6)
C2—N1	1.297 (6)	C7—H7	0.9300
C2—N2	1.339 (5)	C8—F2	1.342 (5)
C3—N2	1.435 (5)	C8—C9	1.361 (7)
C3—C4	1.541 (6)	C9—C10	1.376 (6)
C3—H3	0.9800	C9—H9	0.9300
C4—O1	1.196 (5)	C10—H10	0.9300
C4—C5	1.483 (6)	N2—N3	1.365 (5)
N3—C1—N1	116.8 (4)	F1—C6—C5	119.9 (4)
N3—C1—H1	121.6	C7—C6—C5	123.7 (4)
N1—C1—H1	121.6	C8—C7—C6	117.1 (4)
N1—C2—N2	111.8 (4)	C8—C7—H7	121.5
N1—C2—Br1	125.4 (3)	C6—C7—H7	121.5
N2—C2—Br1	122.8 (3)	F2—C8—C7	118.1 (4)
N2—C3—C4	109.4 (3)	F2—C8—C9	118.7 (4)
N2—C3—Br2	110.5 (3)	C7—C8—C9	123.2 (4)
C4—C3—Br2	110.1 (3)	C8—C9—C10	117.8 (4)
N2—C3—H3	108.9	C8—C9—H9	121.1
C4—C3—H3	108.9	C10—C9—H9	121.1
Br2—C3—H3	108.9	C9—C10—C5	122.0 (4)
O1—C4—C5	120.8 (4)	C9—C10—H10	119.0
O1—C4—C3	120.2 (4)	C5—C10—H10	119.0
C5—C4—C3	119.0 (3)	C2—N1—C1	101.5 (4)
C6—C5—C10	116.2 (4)	C2—N2—N3	109.1 (4)
C6—C5—C4	127.1 (4)	C2—N2—C3	130.4 (4)
C10—C5—C4	116.7 (4)	N3—N2—C3	120.5 (3)
F1—C6—C7	116.4 (3)	C1—N3—N2	100.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1i	0.93	2.55	3.229 (5)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O1i	0.93	2.55	3.229 (5)	130

Symmetry code: (i) .