1-[4-Bromo-2-(tri-fluoro-meth-oxy)phen-yl]-3-methyl-1H-1,2,4-triazole.

In the title compound, C10H7BrF3N3O, the dihedral angle between the benzene and triazole rings is 23.17 (12)° and the C atom of the -CF3 group deviates from its attached ring plane by 1.147 (3) Å. In the crystal, mol-ecules are linked by C-H⋯N inter-actions, generating C(7) chains running along [010].

Related literature

For the anti­bacterial activity of 1,2,4-triazoles, see: Gabriela et al. (2009 ▶); Palekar et al. (2009 ▶). For their anti­viral activity, see: Upmanyu et al. (2006 ▶). For anti­microbial agents, see: Badr & Barwa (2011 ▶), and for anti­mycotic activity such as voriconazole, see: Haber (2001 ▶).

Experimental

Crystal data

C10H7BrF3N3O

M = 322.10

Monoclinic,

a = 5.2389 (3) Å

b = 16.1548 (8) Å

c = 14.0315 (7) Å

β = 92.673 (3)°

V = 1186.24 (11) Å3

Z = 4

Mo Kα radiation

μ = 3.50 mm−1

T = 293 K

0.33 × 0.21 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.419, T max = 0.613

37092 measured reflections

3499 independent reflections

2373 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.135

S = 0.99

3499 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.68 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT-Plus (Bruker, 2009 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814010083/hb7221sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814010083/hb7221Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814010083/hb7221Isup3.cml

CCDC reference: 1000730

Additional supporting information: crystallographic information; 3D view; checkCIF report

C10H7BrF3N3O	Prism
Mr = 322.10	Dx = 1.804 Mg m−3
Monoclinic, P21/n	Melting point: 453 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 5.2389 (3) Å	Cell parameters from 25 reflections
b = 16.1548 (8) Å	θ = 1.9–30.1°
c = 14.0315 (7) Å	µ = 3.50 mm−1
β = 92.673 (3)°	T = 293 K
V = 1186.24 (11) Å3	Prism, colourless
Z = 4	0.33 × 0.21 × 0.14 mm
F(000) = 632

Bruker APEXII CCD diffractometer	3499 independent reflections
Radiation source: fine-focus sealed tube	2373 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
ω scans	θmax = 30.1°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −7→7
Tmin = 0.419, Tmax = 0.613	k = −22→22
37092 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)] = 0.038	H-atom parameters constrained
wR(F2) = 0.135	w = 1/[σ2(Fo2) + (0.0871P)2 + 0.1014P] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max = 0.001
3499 reflections	Δρmax = 0.41 e Å−3
165 parameters	Δρmin = −0.68 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0045 (16)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C1	−0.1456 (5)	0.66662 (15)	0.14761 (15)	0.0523 (5)
C2	0.0451 (4)	0.63544 (14)	0.20903 (15)	0.0524 (5)
H2	0.1392	0.6703	0.2500	0.063*
C3	0.0922 (4)	0.55182 (13)	0.20808 (14)	0.0453 (4)
C4	−0.0376 (4)	0.49886 (12)	0.14480 (14)	0.0427 (4)
C5	−0.2245 (4)	0.53249 (14)	0.08273 (16)	0.0524 (5)
H5	−0.3122	0.4982	0.0392	0.063*
C6	−0.2820 (5)	0.61578 (15)	0.08462 (17)	0.0559 (5)
H6	−0.4107	0.6374	0.0441	0.067*
N1	0.0066 (3)	0.41252 (11)	0.14056 (12)	0.0446 (4)
C7	0.2131 (4)	0.36565 (15)	0.16360 (18)	0.0541 (5)
H7	0.3662	0.3859	0.1905	0.065*
C8	−0.0743 (4)	0.28860 (13)	0.10549 (17)	0.0508 (5)
C9	−0.2132 (6)	0.21249 (15)	0.0729 (3)	0.0708 (8)
H9A	−0.3924	0.2244	0.0646	0.106*
H9B	−0.1874	0.1697	0.1198	0.106*
H9C	−0.1494	0.1944	0.0134	0.106*
C10	0.2286 (6)	0.50572 (18)	0.36008 (19)	0.0688 (7)
N2	−0.1818 (3)	0.36208 (11)	0.10201 (14)	0.0492 (4)
N3	0.1693 (4)	0.28792 (12)	0.14296 (18)	0.0582 (5)
O1	0.2873 (3)	0.51928 (11)	0.26983 (13)	0.0592 (4)
F1	0.0294 (6)	0.45837 (17)	0.36571 (16)	0.1342 (11)
F2	0.4236 (6)	0.46877 (15)	0.40292 (16)	0.1310 (10)
F3	0.1867 (5)	0.57307 (12)	0.40782 (12)	0.0998 (6)
Br1	−0.22139 (7)	0.780974 (16)	0.14867 (2)	0.07657 (17)

	U11	U22	U33	U12	U13	U23
C1	0.0645 (12)	0.0470 (11)	0.0453 (11)	0.0065 (9)	0.0010 (9)	0.0023 (8)
C2	0.0605 (12)	0.0480 (11)	0.0478 (11)	−0.0036 (9)	−0.0062 (9)	−0.0017 (8)
C3	0.0458 (10)	0.0467 (10)	0.0425 (10)	0.0017 (8)	−0.0066 (8)	0.0012 (8)
C4	0.0415 (9)	0.0416 (10)	0.0447 (10)	0.0022 (7)	−0.0012 (7)	−0.0007 (8)
C5	0.0536 (11)	0.0507 (11)	0.0514 (12)	0.0059 (9)	−0.0128 (9)	−0.0030 (9)
C6	0.0634 (13)	0.0511 (12)	0.0520 (12)	0.0118 (10)	−0.0099 (10)	0.0037 (9)
N1	0.0415 (8)	0.0438 (9)	0.0479 (9)	0.0036 (6)	−0.0040 (6)	−0.0028 (7)
C7	0.0411 (10)	0.0539 (12)	0.0664 (14)	0.0093 (9)	−0.0077 (9)	−0.0052 (10)
C8	0.0507 (11)	0.0471 (12)	0.0547 (12)	0.0030 (8)	0.0024 (9)	−0.0046 (9)
C9	0.0684 (16)	0.0487 (14)	0.095 (2)	−0.0032 (10)	0.0046 (14)	−0.0127 (12)
C10	0.0948 (19)	0.0510 (13)	0.0577 (15)	0.0047 (12)	−0.0265 (13)	0.0011 (10)
N2	0.0410 (8)	0.0462 (9)	0.0598 (10)	−0.0013 (7)	−0.0046 (7)	−0.0023 (8)
N3	0.0511 (10)	0.0518 (11)	0.0713 (14)	0.0114 (8)	−0.0016 (9)	−0.0039 (8)
O1	0.0567 (8)	0.0600 (9)	0.0589 (9)	0.0055 (7)	−0.0205 (7)	−0.0029 (7)
F1	0.181 (2)	0.139 (2)	0.0812 (14)	−0.080 (2)	−0.0096 (15)	0.0274 (13)
F2	0.177 (2)	0.1229 (19)	0.0866 (14)	0.0713 (17)	−0.0627 (15)	−0.0062 (13)
F3	0.1628 (19)	0.0694 (11)	0.0658 (10)	0.0264 (12)	−0.0112 (11)	−0.0113 (8)
Br1	0.1162 (3)	0.04531 (19)	0.0671 (2)	0.01567 (12)	−0.00788 (17)	0.00117 (10)

C1—C6	1.381 (3)	N1—N2	1.372 (2)
C1—C2	1.383 (3)	C7—N3	1.307 (3)
C1—Br1	1.890 (2)	C7—H7	0.9300
C2—C3	1.373 (3)	C8—N2	1.314 (3)
C2—H2	0.9300	C8—N3	1.358 (3)
C3—C4	1.388 (3)	C8—C9	1.490 (3)
C3—O1	1.410 (2)	C9—H9A	0.9600
C4—C5	1.390 (3)	C9—H9B	0.9600
C4—N1	1.416 (3)	C9—H9C	0.9600
C5—C6	1.379 (3)	C10—F1	1.299 (4)
C5—H5	0.9300	C10—F2	1.306 (3)
C6—H6	0.9300	C10—F3	1.302 (3)
N1—C7	1.347 (3)	C10—O1	1.335 (3)
C6—C1—C2	121.3 (2)	N3—C7—N1	110.9 (2)
C6—C1—Br1	118.93 (17)	N3—C7—H7	124.6
C2—C1—Br1	119.80 (17)	N1—C7—H7	124.6
C3—C2—C1	118.5 (2)	N2—C8—N3	114.54 (19)
C3—C2—H2	120.8	N2—C8—C9	122.1 (2)
C1—C2—H2	120.8	N3—C8—C9	123.3 (2)
C2—C3—C4	121.97 (18)	C8—C9—H9A	109.5
C2—C3—O1	119.08 (18)	C8—C9—H9B	109.5
C4—C3—O1	118.86 (18)	H9A—C9—H9B	109.5
C5—C4—C3	118.01 (19)	C8—C9—H9C	109.5
C5—C4—N1	118.07 (18)	H9A—C9—H9C	109.5
C3—C4—N1	123.91 (18)	H9B—C9—H9C	109.5
C4—C5—C6	121.1 (2)	F1—C10—F2	108.4 (3)
C4—C5—H5	119.4	F1—C10—F3	107.8 (3)
C6—C5—H5	119.4	F2—C10—F3	107.0 (2)
C1—C6—C5	119.0 (2)	F1—C10—O1	112.0 (2)
C1—C6—H6	120.5	F2—C10—O1	107.6 (3)
C5—C6—H6	120.5	F3—C10—O1	113.8 (2)
C7—N1—N2	108.42 (17)	C8—N2—N1	102.87 (16)
C7—N1—C4	132.43 (18)	C7—N3—C8	103.32 (18)
N2—N1—C4	119.06 (16)	C10—O1—C3	116.85 (18)
C6—C1—C2—C3	−1.7 (3)	C3—C4—N1—N2	157.37 (19)
Br1—C1—C2—C3	178.63 (17)	N2—N1—C7—N3	−0.5 (3)
C1—C2—C3—C4	2.8 (3)	C4—N1—C7—N3	−176.8 (2)
C1—C2—C3—O1	179.54 (19)	N3—C8—N2—N1	−0.3 (3)
C2—C3—C4—C5	−1.6 (3)	C9—C8—N2—N1	178.3 (2)
O1—C3—C4—C5	−178.29 (19)	C7—N1—N2—C8	0.4 (2)
C2—C3—C4—N1	179.3 (2)	C4—N1—N2—C8	177.29 (19)
O1—C3—C4—N1	2.6 (3)	N1—C7—N3—C8	0.3 (3)
C3—C4—C5—C6	−0.8 (3)	N2—C8—N3—C7	0.0 (3)
N1—C4—C5—C6	178.4 (2)	C9—C8—N3—C7	−178.5 (3)
C2—C1—C6—C5	−0.6 (4)	F1—C10—O1—C3	55.1 (3)
Br1—C1—C6—C5	179.06 (18)	F2—C10—O1—C3	174.1 (2)
C4—C5—C6—C1	1.9 (4)	F3—C10—O1—C3	−67.6 (3)
C5—C4—N1—C7	154.2 (2)	C2—C3—O1—C10	81.4 (3)
C3—C4—N1—C7	−26.6 (3)	C4—C3—O1—C10	−101.8 (2)
C5—C4—N1—N2	−21.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N3i	0.93	2.59	3.511 (3)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯N3i	0.93	2.59	3.511 (3)	169

Symmetry code: (i) .