1-[2-(4-Bromo-benz-yloxy)-2-phenyl-ethyl]-1H-1,2,4-triazole.

In the mol-ecule of the title compound, C(17)H(16)BrN(3)O, the triazole ring is oriented at dihedral angles of 6.14 (9)° and 82.08 (9)°, respectively, with respect to the phenyl and bromo-benzene rings. The dihedral angle between the bromo-benzene and phenyl rings is 87.28 (7)°. The intra-molecular C-H⋯O hydrogen bond results in the formation of a planar five-membered ring, which is oriented at a dihedral angle of 0.13 (6)° with respect to the bromo-benzene ring. There is an inter-molecular C-H⋯π contact between a methyl-ene group and the bromo-benzene ring.

Related literature

For general backgroud, see: Paulvannan et al. (2001 ▶); Godefroi et al. (1969 ▶); Özel Güven et al. (2007a ▶,b ▶); Wahbi et al. (1995 ▶). For related literature, see: Peeters et al. (1979 ▶); Freer et al. (1986 ▶); Özel Güven et al. (2008a ▶,b ▶,c ▶,d ▶); Özel Güven, Tahtacı et al. (2008 ▶).

Experimental

Crystal data

C17H16BrN3O

M = 358.24

Monoclinic,

a = 10.2070 (2) Å

b = 13.7948 (3) Å

c = 11.4007 (2) Å

β = 100.317 (1)°

V = 1579.31 (5) Å3

Z = 4

Mo Kα radiation

μ = 2.61 mm−1

T = 120 (2) K

0.38 × 0.30 × 0.20 mm

Data collection

Bruker–Nonius Kappa CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.400, T max = 0.590

18914 measured reflections

3617 independent reflections

2901 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.082

S = 1.05

3617 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.53 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 ▶) and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808027748/xu2450sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027748/xu2450Isup2.hkl

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

C17H16BrN3O	F(000) = 728
Mr = 358.24	Dx = 1.507 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3224 reflections
a = 10.2070 (2) Å	θ = 2.9–27.5°
b = 13.7948 (3) Å	µ = 2.61 mm−1
c = 11.4007 (2) Å	T = 120 K
β = 100.317 (1)°	Block, colorless
V = 1579.31 (5) Å3	0.38 × 0.30 × 0.20 mm
Z = 4

Bruker–Nonius Kappa CCD diffractometer	3617 independent reflections
Radiation source: fine-focus sealed tube	2901 reflections with I > 2σ(I)
graphite	Rint = 0.051
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 3.3°
φ & ω scans	h = −13→12
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −17→17
Tmin = 0.400, Tmax = 0.590	l = −14→14
18914 measured reflections

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0282P)2 + 1.0904P] where P = (Fo2 + 2Fc2)/3
3617 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.53 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
Br	0.01308 (3)	0.204749 (18)	0.24099 (2)	0.03377 (10)
O	0.23831 (15)	0.48903 (11)	0.72395 (13)	0.0219 (3)
N1	0.43625 (18)	0.62535 (13)	0.70844 (15)	0.0209 (4)
N2	0.4116 (2)	0.71851 (14)	0.67091 (18)	0.0262 (4)
N3	0.4832 (2)	0.62873 (15)	0.52812 (17)	0.0264 (4)
C1	0.4421 (2)	0.71587 (17)	0.5630 (2)	0.0260 (5)
H1	0.4357	0.7703	0.5141	0.031*
C2	0.4777 (2)	0.57391 (17)	0.62277 (19)	0.0250 (5)
H2	0.4998	0.5085	0.6287	0.030*
C3	0.4052 (2)	0.59254 (17)	0.82170 (18)	0.0230 (5)
H3A	0.4249	0.6441	0.8800	0.028*
H3B	0.4615	0.5377	0.8500	0.028*
C4	0.2599 (2)	0.56308 (16)	0.81142 (18)	0.0209 (5)
H4	0.2028	0.6187	0.7839	0.025*
C5	0.2348 (2)	0.53134 (16)	0.93291 (18)	0.0203 (5)
C6	0.2718 (2)	0.43995 (17)	0.9773 (2)	0.0264 (5)
H6	0.3090	0.3959	0.9308	0.032*
C7	0.2536 (2)	0.41385 (19)	1.0911 (2)	0.0292 (5)
H7	0.2780	0.3523	1.1202	0.035*
C8	0.1994 (3)	0.47886 (19)	1.1609 (2)	0.0306 (6)
H8	0.1876	0.4614	1.2371	0.037*
C9	0.1627 (3)	0.57037 (19)	1.1170 (2)	0.0323 (6)
H9	0.1269	0.6147	1.1640	0.039*
C10	0.1791 (2)	0.59612 (18)	1.0031 (2)	0.0263 (5)
H10	0.1527	0.6572	0.9734	0.032*
C11	0.1027 (2)	0.45894 (17)	0.69514 (19)	0.0220 (5)
H11A	0.0452	0.5153	0.6806	0.026*
H11B	0.0788	0.4230	0.7613	0.026*
C12	0.0843 (2)	0.39583 (16)	0.58547 (18)	0.0199 (5)
C13	0.1877 (2)	0.37627 (17)	0.52494 (19)	0.0224 (5)
H13	0.2718	0.4021	0.5525	0.027*
C14	0.1669 (2)	0.31831 (17)	0.42329 (19)	0.0240 (5)
H14	0.2367	0.3050	0.3833	0.029*
C15	0.0416 (2)	0.28084 (16)	0.38240 (19)	0.0242 (5)
C16	−0.0634 (2)	0.30004 (17)	0.4409 (2)	0.0247 (5)
H16	−0.1475	0.2748	0.4125	0.030*
C17	−0.0413 (2)	0.35727 (17)	0.54222 (19)	0.0225 (5)
H17	−0.1114	0.3702	0.5820	0.027*

	U11	U22	U33	U12	U13	U23
Br	0.04619 (18)	0.02724 (15)	0.02419 (14)	−0.00004 (12)	−0.00363 (11)	−0.00854 (10)
O	0.0210 (8)	0.0264 (8)	0.0189 (7)	−0.0031 (7)	0.0056 (6)	−0.0072 (6)
N1	0.0236 (10)	0.0210 (10)	0.0190 (9)	−0.0032 (8)	0.0061 (8)	0.0008 (8)
N2	0.0307 (11)	0.0202 (10)	0.0295 (10)	−0.0027 (8)	0.0105 (9)	0.0003 (8)
N3	0.0287 (11)	0.0280 (11)	0.0247 (10)	0.0014 (9)	0.0107 (8)	0.0027 (8)
C1	0.0263 (12)	0.0263 (13)	0.0274 (12)	0.0006 (10)	0.0102 (10)	0.0078 (10)
C2	0.0322 (13)	0.0219 (12)	0.0222 (11)	0.0022 (10)	0.0082 (10)	0.0008 (9)
C3	0.0273 (12)	0.0274 (12)	0.0143 (10)	−0.0054 (10)	0.0040 (9)	−0.0010 (9)
C4	0.0250 (12)	0.0220 (11)	0.0165 (10)	−0.0026 (9)	0.0059 (9)	−0.0032 (9)
C5	0.0196 (11)	0.0245 (12)	0.0166 (10)	−0.0050 (9)	0.0026 (9)	−0.0037 (9)
C6	0.0304 (13)	0.0241 (12)	0.0247 (11)	0.0010 (10)	0.0047 (10)	−0.0028 (10)
C7	0.0306 (13)	0.0290 (13)	0.0261 (12)	−0.0018 (11)	0.0002 (10)	0.0080 (10)
C8	0.0322 (14)	0.0404 (15)	0.0207 (11)	−0.0049 (12)	0.0084 (10)	0.0043 (11)
C9	0.0379 (15)	0.0354 (14)	0.0270 (12)	0.0019 (12)	0.0150 (11)	−0.0017 (11)
C10	0.0315 (13)	0.0244 (12)	0.0247 (11)	−0.0008 (10)	0.0097 (10)	0.0010 (10)
C11	0.0217 (11)	0.0250 (12)	0.0197 (11)	−0.0049 (9)	0.0047 (9)	−0.0017 (9)
C12	0.0251 (12)	0.0189 (11)	0.0156 (10)	0.0004 (9)	0.0033 (9)	0.0027 (8)
C13	0.0232 (12)	0.0238 (12)	0.0196 (10)	−0.0020 (9)	0.0018 (9)	−0.0013 (9)
C14	0.0276 (12)	0.0247 (12)	0.0201 (11)	0.0017 (10)	0.0053 (10)	0.0003 (9)
C15	0.0345 (13)	0.0185 (11)	0.0176 (10)	−0.0005 (10)	−0.0009 (10)	0.0012 (9)
C16	0.0244 (12)	0.0233 (12)	0.0236 (11)	−0.0056 (10)	−0.0034 (9)	0.0044 (10)
C17	0.0217 (12)	0.0233 (12)	0.0229 (11)	0.0000 (9)	0.0048 (9)	0.0042 (9)

Br—C15	1.902 (2)	C1—H1	0.9300
O—C4	1.417 (3)	C2—H2	0.9300
O—C11	1.426 (3)	C3—C4	1.523 (3)
N1—C2	1.336 (3)	C3—H3A	0.9700
N1—N2	1.363 (3)	C3—H3B	0.9700
N1—C3	1.456 (3)	C4—C5	1.517 (3)
N2—C1	1.323 (3)	C4—H4	0.9800
N3—C2	1.327 (3)	C5—C10	1.387 (3)
C12—C13	1.387 (3)	C6—C5	1.386 (3)
C12—C11	1.507 (3)	C6—C7	1.390 (3)
C13—C14	1.393 (3)	C6—H6	0.9300
C13—H13	0.9300	C7—H7	0.9300
C14—H14	0.9300	C8—C7	1.379 (4)
C15—C14	1.381 (3)	C8—C9	1.385 (4)
C15—C16	1.385 (3)	C8—H8	0.9300
C16—C17	1.384 (3)	C9—H9	0.9300
C16—H16	0.9300	C10—C9	1.385 (3)
C17—C12	1.394 (3)	C10—H10	0.9300
C17—H17	0.9300	C11—H11A	0.9700
C1—N3	1.356 (3)	C11—H11B	0.9700
C4—O—C11	113.20 (16)	C7—C8—C9	119.6 (2)
C2—N1—N2	109.63 (18)	C7—C8—H8	120.2
C2—N1—C3	129.13 (19)	C9—C8—H8	120.2
N2—N1—C3	120.95 (18)	C8—C9—C10	120.2 (2)
C1—N2—N1	101.85 (19)	C8—C9—H9	119.9
C2—N3—C1	101.93 (19)	C10—C9—H9	119.9
N2—C1—N3	115.7 (2)	C9—C10—C5	120.4 (2)
N2—C1—H1	122.2	C9—C10—H10	119.8
N3—C1—H1	122.2	C5—C10—H10	119.8
N3—C2—N1	110.9 (2)	O—C11—C12	109.32 (18)
N3—C2—H2	124.5	O—C11—H11A	109.8
N1—C2—H2	124.5	C12—C11—H11A	109.8
N1—C3—C4	112.24 (18)	O—C11—H11B	109.8
N1—C3—H3A	109.2	C12—C11—H11B	109.8
C4—C3—H3A	109.2	H11A—C11—H11B	108.3
N1—C3—H3B	109.2	C13—C12—C17	118.9 (2)
C4—C3—H3B	109.2	C13—C12—C11	122.1 (2)
H3A—C3—H3B	107.9	C17—C12—C11	118.9 (2)
O—C4—C5	113.84 (18)	C12—C13—C14	120.6 (2)
O—C4—C3	105.84 (17)	C12—C13—H13	119.7
C5—C4—C3	109.14 (18)	C14—C13—H13	119.7
O—C4—H4	109.3	C15—C14—C13	119.3 (2)
C5—C4—H4	109.3	C15—C14—H14	120.3
C3—C4—H4	109.3	C13—C14—H14	120.3
C6—C5—C10	119.3 (2)	C14—C15—C16	121.0 (2)
C6—C5—C4	121.1 (2)	C14—C15—Br	118.98 (18)
C10—C5—C4	119.6 (2)	C16—C15—Br	119.97 (18)
C5—C6—C7	120.2 (2)	C17—C16—C15	119.1 (2)
C5—C6—H6	119.9	C17—C16—H16	120.4
C7—C6—H6	119.9	C15—C16—H16	120.4
C8—C7—C6	120.3 (2)	C16—C17—C12	121.0 (2)
C8—C7—H7	119.8	C16—C17—H17	119.5
C6—C7—H7	119.8	C12—C17—H17	119.5
C11—O—C4—C5	65.5 (2)	C4—C5—C10—C9	−176.2 (2)
C11—O—C4—C3	−174.60 (17)	C7—C6—C5—C10	−0.2 (3)
C4—O—C11—C12	168.62 (17)	C7—C6—C5—C4	177.1 (2)
C2—N1—N2—C1	−0.5 (2)	C5—C6—C7—C8	−0.5 (4)
C3—N1—N2—C1	−174.8 (2)	C9—C8—C7—C6	0.3 (4)
N2—N1—C2—N3	0.4 (3)	C7—C8—C9—C10	0.6 (4)
C3—N1—C2—N3	174.1 (2)	C5—C10—C9—C8	−1.3 (4)
N2—N1—C3—C4	83.5 (2)	C13—C12—C11—O	−1.9 (3)
C2—N1—C3—C4	−89.6 (3)	C17—C12—C11—O	179.24 (19)
N1—N2—C1—N3	0.4 (3)	C11—C12—C13—C14	−179.4 (2)
C1—N3—C2—N1	−0.1 (3)	C17—C12—C13—C14	−0.6 (3)
N2—C1—N3—C2	−0.2 (3)	C12—C13—C14—C15	0.5 (3)
N1—C3—C4—O	58.0 (2)	Br—C15—C14—C13	178.28 (17)
N1—C3—C4—C5	−179.15 (18)	C16—C15—C14—C13	0.0 (3)
O—C4—C5—C6	38.9 (3)	Br—C15—C16—C17	−178.62 (17)
O—C4—C5—C10	−143.9 (2)	C14—C15—C16—C17	−0.4 (3)
C3—C4—C5—C6	−79.1 (3)	C15—C16—C17—C12	0.2 (3)
C3—C4—C5—C10	98.1 (2)	C16—C17—C12—C11	179.1 (2)
C6—C5—C10—C9	1.1 (4)	C16—C17—C12—C13	0.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O	0.93	2.37	2.723 (3)	102
C11—H11A···Cg3i	0.97	2.84	3.687 (2)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O	0.93	2.37	2.723 (3)	102
C11—H11A⋯Cg3i	0.97	2.84	3.687 (2)	147

Symmetry code: (i) . Cg3 is the centroid of the C12–C17 ring.