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

In the mol-ecule of the title compound, C(17)H(15)Cl(2)N(3)O, the triazole ring is oriented at dihedral angles of 9.24 (6) and 82.49 (6)°, respectively, with respect to the phenyl and dichloro-benzene rings. The dihedral angle between the dichloro-benzene and phenyl rings is 88.57 (5)°. An intra-molecular C-H⋯O contact results in the formation of a planar five-membered 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 structures, see: Peeters et al. (1979 ▶); Freer et al. (1986 ▶); Özel Güven et al. (2008a ▶,b ▶,c ▶,d ▶,e ▶,f ▶).

Experimental

Crystal data

C17H15Cl2N3O

M = 348.22

Monoclinic,

a = 10.5630 (3) Å

b = 13.7933 (5) Å

c = 11.4437 (4) Å

β = 101.840 (2)°

V = 1631.86 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.41 mm−1

T = 296 (2) K

0.35 × 0.25 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.871, T max = 0.942

17794 measured reflections

4055 independent reflections

3135 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.104

S = 1.04

4055 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808039196/su2082sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808039196/su2082Isup2.hkl

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

C17H15Cl2N3O	F000 = 720
Mr = 348.22	Dx = 1.417 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1196 reflections
a = 10.5630 (3) Å	θ = 2.3–28.3º
b = 13.7933 (5) Å	µ = 0.41 mm−1
c = 11.4437 (4) Å	T = 296 (2) K
β = 101.840 (2)º	Rod-shaped, colorless
V = 1631.86 (10) Å3	0.35 × 0.25 × 0.15 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	4055 independent reflections
Radiation source: fine-focus sealed tube	3135 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.026
Detector resolution: 7.40 pixels mm-1	θmax = 28.3º
T = 296(2) K	θmin = 2.3º
ω scans	h = −14→14
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −18→18
Tmin = 0.871, Tmax = 0.942	l = −15→14
17794 measured reflections

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)] = 0.037	H-atom parameters constrained
wR(F2) = 0.104	w = 1/[σ2(Fo2) + (0.0424P)2 + 0.5043P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
4055 reflections	Δρmax = 0.32 e Å−3
208 parameters	Δρmin = −0.24 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
Cl1	0.52852 (6)	0.29276 (4)	−0.26180 (4)	0.07651 (18)
Cl2	0.34215 (4)	0.12684 (4)	0.09114 (5)	0.06649 (16)
O1	0.74240 (10)	0.02400 (8)	0.22002 (9)	0.0471 (3)
N1	0.93446 (12)	−0.11684 (10)	0.21096 (11)	0.0455 (3)
N2	0.90960 (15)	−0.21005 (11)	0.17678 (14)	0.0566 (4)
N3	0.99426 (14)	−0.12858 (12)	0.04041 (13)	0.0576 (4)
C1	0.94814 (17)	−0.21219 (14)	0.07456 (16)	0.0558 (4)
H1	0.9437	−0.2683	0.0288	0.067*
C2	0.98325 (16)	−0.07037 (14)	0.12863 (15)	0.0541 (4)
H2	1.0065	−0.0052	0.1329	0.065*
C3	0.90367 (16)	−0.08020 (14)	0.32066 (13)	0.0508 (4)
H3A	0.9575	−0.0242	0.3472	0.061*
H3B	0.9237	−0.1296	0.3820	0.061*
C4	0.76226 (14)	−0.05147 (12)	0.30597 (12)	0.0420 (3)
H4	0.7075	−0.1069	0.2751	0.050*
C5	0.73484 (14)	−0.02155 (11)	0.42542 (12)	0.0399 (3)
C6	0.77537 (18)	0.06624 (13)	0.47606 (15)	0.0557 (4)
H6	0.8178	0.1096	0.4351	0.067*
C7	0.7537 (2)	0.09083 (14)	0.58750 (16)	0.0615 (5)
H7	0.7809	0.1507	0.6207	0.074*
C8	0.6926 (2)	0.02748 (16)	0.64868 (17)	0.0668 (5)
H8	0.6784	0.0440	0.7237	0.080*
C9	0.6523 (2)	−0.06017 (17)	0.59975 (18)	0.0803 (7)
H9	0.6113	−0.1037	0.6418	0.096*
C10	0.6723 (2)	−0.08442 (14)	0.48764 (16)	0.0612 (5)
H10	0.6431	−0.1438	0.4541	0.073*
C11	0.61158 (14)	0.05336 (12)	0.18708 (13)	0.0423 (3)
H11A	0.5879	0.0904	0.2514	0.051*
H11B	0.5560	−0.0032	0.1725	0.051*
C12	0.59372 (13)	0.11430 (10)	0.07624 (12)	0.0384 (3)
C13	0.69449 (15)	0.13512 (12)	0.01952 (13)	0.0462 (4)
H13	0.7767	0.1113	0.0512	0.055*
C14	0.67532 (17)	0.19065 (13)	−0.08330 (14)	0.0516 (4)
H14	0.7441	0.2042	−0.1201	0.062*
C15	0.55413 (17)	0.22549 (12)	−0.13037 (13)	0.0493 (4)
C16	0.45097 (16)	0.20677 (11)	−0.07723 (14)	0.0472 (4)
H16	0.3689	0.2305	−0.1097	0.057*
C17	0.47304 (14)	0.15158 (11)	0.02584 (13)	0.0414 (3)

	U11	U22	U33	U12	U13	U23
Cl1	0.0977 (4)	0.0735 (3)	0.0540 (3)	0.0099 (3)	0.0054 (2)	0.0273 (2)
Cl2	0.0427 (2)	0.0853 (4)	0.0740 (3)	0.0131 (2)	0.0178 (2)	0.0169 (2)
O1	0.0397 (5)	0.0633 (7)	0.0391 (5)	0.0109 (5)	0.0102 (4)	0.0171 (5)
N1	0.0429 (7)	0.0529 (8)	0.0419 (7)	0.0123 (6)	0.0114 (5)	0.0047 (6)
N2	0.0617 (9)	0.0497 (8)	0.0615 (9)	0.0087 (7)	0.0194 (7)	0.0056 (7)
N3	0.0511 (8)	0.0718 (10)	0.0559 (8)	0.0001 (7)	0.0246 (7)	−0.0063 (7)
C1	0.0504 (9)	0.0594 (11)	0.0600 (10)	0.0083 (8)	0.0170 (8)	−0.0083 (8)
C2	0.0532 (9)	0.0570 (10)	0.0563 (10)	−0.0027 (8)	0.0214 (8)	−0.0003 (8)
C3	0.0498 (9)	0.0656 (11)	0.0367 (7)	0.0176 (8)	0.0081 (6)	0.0062 (7)
C4	0.0447 (8)	0.0478 (8)	0.0340 (7)	0.0067 (6)	0.0093 (6)	0.0057 (6)
C5	0.0413 (7)	0.0441 (8)	0.0342 (7)	0.0067 (6)	0.0074 (6)	0.0038 (6)
C6	0.0672 (11)	0.0508 (10)	0.0492 (9)	−0.0085 (8)	0.0125 (8)	0.0027 (7)
C7	0.0751 (12)	0.0524 (10)	0.0533 (10)	0.0016 (9)	0.0043 (9)	−0.0124 (8)
C8	0.0790 (13)	0.0802 (14)	0.0453 (9)	0.0048 (11)	0.0223 (9)	−0.0111 (9)
C9	0.1129 (18)	0.0828 (15)	0.0574 (11)	−0.0245 (13)	0.0460 (12)	−0.0075 (11)
C10	0.0840 (13)	0.0552 (10)	0.0509 (9)	−0.0154 (9)	0.0291 (9)	−0.0069 (8)
C11	0.0389 (7)	0.0511 (9)	0.0378 (7)	0.0090 (6)	0.0103 (6)	0.0060 (6)
C12	0.0407 (7)	0.0402 (8)	0.0334 (6)	0.0047 (6)	0.0055 (5)	−0.0018 (6)
C13	0.0413 (8)	0.0567 (9)	0.0402 (8)	0.0082 (7)	0.0073 (6)	0.0060 (7)
C14	0.0535 (9)	0.0578 (10)	0.0448 (8)	0.0019 (7)	0.0128 (7)	0.0085 (7)
C15	0.0646 (10)	0.0430 (9)	0.0373 (7)	0.0048 (7)	0.0033 (7)	0.0056 (6)
C16	0.0493 (9)	0.0432 (8)	0.0442 (8)	0.0108 (7)	−0.0014 (7)	−0.0013 (6)
C17	0.0405 (7)	0.0412 (8)	0.0418 (7)	0.0050 (6)	0.0064 (6)	−0.0037 (6)

Cl1—C15	1.7404 (16)	C6—H6	0.9300
Cl2—C17	1.7351 (16)	C7—H7	0.9300
O1—C4	1.4178 (17)	C8—C7	1.362 (3)
O1—C11	1.4148 (17)	C8—C9	1.363 (3)
N1—N2	1.354 (2)	C8—H8	0.9300
N1—C2	1.328 (2)	C9—C10	1.383 (2)
N1—C3	1.4508 (19)	C9—H9	0.9300
N3—C1	1.341 (2)	C10—H10	0.9300
N3—C2	1.314 (2)	C11—H11A	0.9700
C1—N2	1.315 (2)	C11—H11B	0.9700
C1—H1	0.9300	C12—C11	1.5010 (19)
C2—H2	0.9300	C12—C13	1.386 (2)
C3—H3A	0.9700	C12—C17	1.386 (2)
C3—H3B	0.9700	C13—C14	1.384 (2)
C4—C3	1.521 (2)	C13—H13	0.9300
C4—H4	0.9800	C14—H14	0.9300
C5—C4	1.5117 (19)	C15—C14	1.370 (2)
C5—C6	1.373 (2)	C15—C16	1.377 (2)
C5—C10	1.375 (2)	C16—H16	0.9300
C6—C7	1.383 (2)	C17—C16	1.383 (2)
C11—O1—C4	113.10 (11)	C7—C8—C9	119.91 (17)
N2—N1—C3	121.08 (14)	C7—C8—H8	120.0
C2—N1—N2	109.51 (14)	C9—C8—H8	120.0
C2—N1—C3	129.37 (15)	C8—C9—C10	120.08 (19)
C1—N2—N1	101.60 (14)	C8—C9—H9	120.0
C2—N3—C1	101.94 (14)	C10—C9—H9	120.0
N2—C1—N3	115.92 (16)	C5—C10—C9	120.59 (18)
N2—C1—H1	122.0	C5—C10—H10	119.7
N3—C1—H1	122.0	C9—C10—H10	119.7
N1—C2—H2	124.5	O1—C11—C12	109.39 (11)
N3—C2—N1	111.02 (16)	O1—C11—H11A	109.8
N3—C2—H2	124.5	O1—C11—H11B	109.8
N1—C3—C4	112.62 (13)	C12—C11—H11A	109.8
N1—C3—H3A	109.1	C12—C11—H11B	109.8
N1—C3—H3B	109.1	H11A—C11—H11B	108.2
C4—C3—H3A	109.1	C13—C12—C11	122.44 (13)
C4—C3—H3B	109.1	C17—C12—C11	120.33 (13)
H3A—C3—H3B	107.8	C17—C12—C13	117.22 (13)
O1—C4—C3	105.67 (12)	C12—C13—H13	119.3
O1—C4—C5	113.48 (12)	C14—C13—C12	121.37 (14)
O1—C4—H4	109.3	C14—C13—H13	119.3
C3—C4—H4	109.3	C13—C14—H14	120.3
C5—C4—C3	109.70 (12)	C15—C14—C13	119.37 (15)
C5—C4—H4	109.3	C15—C14—H14	120.3
C6—C5—C4	121.44 (14)	C14—C15—Cl1	119.59 (14)
C6—C5—C10	118.65 (15)	C14—C15—C16	121.40 (14)
C10—C5—C4	119.86 (14)	C15—C16—C17	118.01 (14)
C5—C6—C7	120.62 (17)	C15—C16—H16	121.0
C5—C6—H6	119.7	C16—C15—Cl1	119.00 (13)
C7—C6—H6	119.7	C17—C16—H16	121.0
C6—C7—H7	119.9	C12—C17—Cl2	119.60 (12)
C8—C7—C6	120.13 (17)	C16—C17—Cl2	117.76 (12)
C8—C7—H7	119.9	C16—C17—C12	122.62 (14)
C11—O1—C4—C5	−65.39 (16)	C6—C5—C10—C9	−0.9 (3)
C11—O1—C4—C3	174.37 (13)	C5—C6—C7—C8	0.5 (3)
C4—O1—C11—C12	−166.09 (12)	C9—C8—C7—C6	−0.2 (3)
C2—N1—N2—C1	0.78 (17)	C7—C8—C9—C10	−0.6 (4)
C3—N1—N2—C1	178.59 (14)	C8—C9—C10—C5	1.2 (4)
N2—N1—C2—N3	−0.86 (19)	C13—C12—C11—O1	0.3 (2)
C3—N1—C2—N3	−178.43 (14)	C17—C12—C11—O1	179.72 (13)
N2—N1—C3—C4	−81.93 (18)	C11—C12—C13—C14	179.31 (15)
C2—N1—C3—C4	95.4 (2)	C17—C12—C13—C14	−0.1 (2)
C1—N3—C2—N1	0.51 (19)	C11—C12—C17—Cl2	−0.4 (2)
C2—N3—C1—N2	0.0 (2)	C11—C12—C17—C16	−178.91 (14)
N3—C1—N2—N1	−0.5 (2)	C13—C12—C17—Cl2	179.09 (12)
O1—C4—C3—N1	−61.74 (18)	C13—C12—C17—C16	0.5 (2)
C5—C4—C3—N1	175.58 (14)	C12—C13—C14—C15	−0.3 (3)
C6—C5—C4—O1	−42.85 (19)	Cl1—C15—C14—C13	−178.35 (13)
C6—C5—C4—C3	75.08 (19)	C16—C15—C14—C13	0.3 (3)
C10—C5—C4—O1	139.60 (16)	Cl1—C15—C16—C17	178.75 (12)
C10—C5—C4—C3	−102.47 (18)	C14—C15—C16—C17	0.1 (2)
C4—C5—C6—C7	−177.53 (16)	Cl2—C17—C16—C15	−179.10 (12)
C10—C5—C6—C7	0.0 (3)	C12—C17—C16—C15	−0.5 (2)
C4—C5—C10—C9	176.68 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1	0.93	2.37	2.7191 (18)	102

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O1	0.93	2.37	2.7191 (18)	102

Symmetry code: (i) .