1-[2-(2,4-Dichloro-benz-yloxy)-2-(2-fur-yl)eth-yl]-1H-1,2,4-triazole.

In the mol-ecule of the title compound, C(15)H(13)Cl(2)N(3)O(2), the triazole ring is oriented at dihedral angles of 14.8 (2) and 81.5 (1)° to the furan and dichloro-benzene rings, respectively. The dihedral angle between the dichloro-benzene and furan rings is 86.3 (2)°. An intra-molecular C-H⋯O hydrogen bond results in the formation of a planar [maximum deviation 0.012 (2) Å] five-membered ring, which is oriented at a dihedral angle of 0.90 (7)° with respect to the dichloro-benzene ring. There is an inter-molecular C-H⋯π contact between the methyl-ene group and the dichloro-benzene ring.

Related literature

For general background to the use of ether structures containing 1H-imidazole and 1H-1,2,4-triazole rings as anti­fungal agents, see: Caira et al. (2004 ▶); Godefroi et al. (1969 ▶); Özel Güven et al. (2007a ▶,b ▶); Paulvannan et al. (2001 ▶); Peeters et al. (1996 ▶); Wahbi et al. (1995 ▶). For related structures, see: Freer et al. (1986 ▶); Özel Güven et al. (2008a ▶,b ▶,c ▶,d ▶,e ▶,f ▶); Peeters et al. (1979 ▶).

Experimental

Crystal data

C15H13Cl2N3O2

M = 338.18

Monoclinic,

a = 10.6057 (2) Å

b = 13.3560 (3) Å

c = 11.1919 (2) Å

β = 101.170 (1)°

V = 1555.30 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.43 mm−1

T = 120 K

0.50 × 0.35 × 0.20 mm

Data collection

Bruker–Nonius Kappa CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.815, T max = 0.920

6687 measured reflections

3547 independent reflections

2522 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.161

S = 1.06

3547 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.77 e Å−3

Δρmin = −0.33 e Å−3

Data collection: COLLECT (Nonius, 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 (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809044018/ci2951sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044018/ci2951Isup2.hkl

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

C15H13Cl2N3O2	F(000) = 696
Mr = 338.18	Dx = 1.444 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3274 reflections
a = 10.6057 (2) Å	θ = 2.9–27.5°
b = 13.3560 (3) Å	µ = 0.43 mm−1
c = 11.1919 (2) Å	T = 120 K
β = 101.170 (1)°	Plate, colourless
V = 1555.30 (5) Å3	0.50 × 0.35 × 0.20 mm
Z = 4

Bruker–Nonius Kappa CCD diffractometer	3547 independent reflections
Radiation source: fine-focus sealed tube	2522 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −13→13
Tmin = 0.815, Tmax = 0.920	k = −17→17
6687 measured reflections	l = −14→14

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0852P)2 + 0.4221P] where P = (Fo2 + 2Fc2)/3
3547 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 0.77 e Å−3
0 restraints	Δρmin = −0.32 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
Cl1	0.48306 (8)	0.29223 (6)	0.76970 (7)	0.0823 (3)
Cl2	0.66147 (6)	0.12991 (6)	0.39547 (7)	0.0719 (3)
O1	0.26246 (14)	0.02290 (13)	0.27553 (13)	0.0523 (4)
O2	0.20740 (18)	0.07592 (15)	0.01684 (16)	0.0673 (5)
N1	0.06121 (18)	−0.11249 (15)	0.27806 (16)	0.0498 (5)
N2	0.0878 (2)	−0.20960 (17)	0.3093 (2)	0.0648 (6)
N3	0.0001 (2)	−0.13162 (18)	0.45167 (19)	0.0644 (6)
C1	0.0492 (3)	−0.2156 (2)	0.4135 (3)	0.0657 (7)
H1	0.0556	−0.2746	0.4583	0.079*
C2	0.0106 (3)	−0.0688 (2)	0.3648 (2)	0.0598 (6)
H2	−0.0142	−0.0019	0.3637	0.072*
C3	0.0914 (2)	−0.0710 (2)	0.16712 (19)	0.0550 (6)
H3A	0.0425	−0.0100	0.1464	0.066*
H3B	0.0658	−0.1183	0.1011	0.066*
C4	0.2337 (2)	−0.04811 (18)	0.17976 (19)	0.0495 (5)
H4	0.2831	−0.1093	0.2036	0.059*
C5	0.2625 (2)	−0.01101 (19)	0.0610 (2)	0.0505 (5)
C6	0.2450 (3)	0.0932 (3)	−0.0918 (2)	0.0760 (8)
H6	0.2218	0.1486	−0.1416	0.091*
C7	0.3176 (4)	0.0206 (3)	−0.1140 (3)	0.0926 (11)
H7	0.3551	0.0147	−0.1823	0.111*
C8	0.3303 (3)	−0.0490 (3)	−0.0155 (3)	0.0884 (10)
H8	0.3765	−0.1086	−0.0071	0.106*
C9	0.3934 (2)	0.05052 (18)	0.30581 (19)	0.0460 (5)
H9A	0.4171	0.0885	0.2396	0.055*
H9B	0.4468	−0.0089	0.3191	0.055*
C10	0.4136 (2)	0.11323 (16)	0.41992 (18)	0.0430 (5)
C11	0.3143 (2)	0.13351 (19)	0.4814 (2)	0.0528 (6)
H11	0.2325	0.1087	0.4508	0.063*
C12	0.3349 (2)	0.1896 (2)	0.5868 (2)	0.0590 (6)
H12	0.2674	0.2025	0.6267	0.071*
C13	0.4554 (2)	0.22648 (19)	0.6326 (2)	0.0547 (6)
C14	0.5566 (2)	0.20958 (18)	0.5743 (2)	0.0532 (6)
H14	0.6379	0.2351	0.6052	0.064*
C15	0.5333 (2)	0.15318 (17)	0.4678 (2)	0.0470 (5)

	U11	U22	U33	U12	U13	U23
Cl1	0.1025 (6)	0.0819 (6)	0.0616 (4)	−0.0194 (4)	0.0135 (4)	−0.0290 (4)
Cl2	0.0461 (4)	0.0894 (6)	0.0834 (5)	−0.0112 (3)	0.0204 (3)	−0.0183 (4)
O1	0.0435 (8)	0.0694 (11)	0.0444 (8)	−0.0108 (7)	0.0093 (6)	−0.0156 (7)
O2	0.0722 (12)	0.0746 (13)	0.0579 (10)	0.0045 (10)	0.0191 (8)	0.0056 (9)
N1	0.0488 (10)	0.0542 (12)	0.0468 (10)	−0.0102 (9)	0.0101 (8)	−0.0052 (8)
N2	0.0735 (14)	0.0536 (13)	0.0701 (14)	−0.0059 (11)	0.0206 (11)	−0.0055 (10)
N3	0.0621 (13)	0.0746 (16)	0.0615 (12)	0.0017 (11)	0.0249 (10)	0.0094 (11)
C1	0.0627 (16)	0.0617 (17)	0.0743 (17)	−0.0078 (13)	0.0171 (13)	0.0120 (13)
C2	0.0644 (15)	0.0610 (16)	0.0577 (13)	0.0051 (12)	0.0213 (11)	0.0013 (12)
C3	0.0521 (13)	0.0703 (16)	0.0415 (11)	−0.0148 (11)	0.0069 (9)	−0.0046 (10)
C4	0.0505 (12)	0.0546 (14)	0.0431 (11)	−0.0075 (10)	0.0086 (9)	−0.0083 (10)
C5	0.0482 (12)	0.0583 (14)	0.0466 (11)	−0.0061 (11)	0.0133 (9)	−0.0116 (10)
C6	0.081 (2)	0.095 (2)	0.0525 (14)	−0.0173 (18)	0.0141 (13)	0.0096 (15)
C7	0.101 (2)	0.125 (3)	0.0621 (17)	−0.008 (2)	0.0413 (17)	−0.0092 (18)
C8	0.099 (2)	0.100 (3)	0.0766 (19)	0.0192 (19)	0.0428 (18)	−0.0125 (17)
C9	0.0430 (11)	0.0520 (13)	0.0437 (10)	−0.0073 (10)	0.0101 (8)	−0.0030 (9)
C10	0.0439 (11)	0.0428 (12)	0.0416 (10)	−0.0036 (9)	0.0067 (8)	0.0020 (8)
C11	0.0455 (12)	0.0633 (16)	0.0495 (12)	−0.0082 (10)	0.0094 (9)	−0.0073 (10)
C12	0.0594 (14)	0.0677 (16)	0.0518 (13)	−0.0041 (12)	0.0157 (11)	−0.0110 (11)
C13	0.0670 (15)	0.0499 (14)	0.0456 (12)	−0.0063 (11)	0.0072 (10)	−0.0063 (10)
C14	0.0548 (13)	0.0495 (14)	0.0508 (12)	−0.0109 (10)	−0.0009 (10)	0.0008 (10)
C15	0.0434 (11)	0.0479 (13)	0.0493 (11)	−0.0030 (9)	0.0083 (9)	0.0026 (9)

Cl1—C13	1.742 (2)	C5—C8	1.321 (3)
Cl2—C15	1.740 (2)	C6—H6	0.93
O1—C4	1.419 (3)	C7—C6	1.293 (5)
O1—C9	1.413 (2)	C7—H7	0.93
O2—C5	1.350 (3)	C8—C7	1.428 (5)
O2—C6	1.370 (3)	C8—H8	0.93
N1—N2	1.358 (3)	C9—H9A	0.97
N1—C2	1.332 (3)	C9—H9B	0.97
N1—C3	1.451 (3)	C10—C15	1.386 (3)
N2—C1	1.311 (3)	C10—C11	1.391 (3)
N3—C1	1.341 (4)	C10—C9	1.508 (3)
N3—C2	1.305 (3)	C11—C12	1.379 (3)
C1—H1	0.93	C11—H11	0.93
C2—H2	0.93	C12—H12	0.93
C3—H3A	0.97	C13—C12	1.373 (3)
C3—H3B	0.97	C14—C13	1.378 (4)
C4—C3	1.519 (3)	C14—C15	1.391 (3)
C4—C5	1.504 (3)	C14—H14	0.93
C4—H4	0.98
C9—O1—C4	114.40 (16)	C6—C7—C8	108.0 (3)
C5—O2—C6	106.9 (2)	C6—C7—H7	126.0
N2—N1—C3	121.0 (2)	C8—C7—H7	126.0
C2—N1—N2	108.9 (2)	C5—C8—C7	105.6 (3)
C2—N1—C3	130.1 (2)	C5—C8—H8	127.2
C1—N2—N1	101.6 (2)	C7—C8—H8	127.2
C2—N3—C1	101.9 (2)	O1—C9—C10	108.67 (17)
N2—C1—N3	116.1 (2)	O1—C9—H9A	110.0
N2—C1—H1	121.9	O1—C9—H9B	110.0
N3—C1—H1	121.9	C10—C9—H9A	110.0
N1—C2—H2	124.3	C10—C9—H9B	110.0
N3—C2—N1	111.4 (2)	H9A—C9—H9B	108.3
N3—C2—H2	124.3	C11—C10—C9	122.02 (19)
N1—C3—C4	112.17 (18)	C15—C10—C9	120.72 (19)
N1—C3—H3A	109.2	C15—C10—C11	117.3 (2)
N1—C3—H3B	109.2	C10—C11—H11	119.4
C4—C3—H3A	109.2	C12—C11—C10	121.3 (2)
C4—C3—H3B	109.2	C12—C11—H11	119.4
H3A—C3—H3B	107.9	C11—C12—H12	120.1
O1—C4—C5	113.35 (19)	C13—C12—C11	119.8 (2)
O1—C4—C3	105.63 (18)	C13—C12—H12	120.1
O1—C4—H4	109.0	C12—C13—Cl1	119.7 (2)
C3—C4—H4	109.0	C12—C13—C14	121.2 (2)
C5—C4—C3	110.63 (18)	C14—C13—Cl1	119.08 (19)
C5—C4—H4	109.0	C13—C14—C15	118.0 (2)
O2—C5—C4	117.3 (2)	C13—C14—H14	121.0
C8—C5—O2	110.1 (3)	C15—C14—H14	121.0
C8—C5—C4	132.5 (3)	C10—C15—Cl2	119.41 (17)
O2—C6—H6	125.3	C10—C15—C14	122.5 (2)
C7—C6—O2	109.3 (3)	C14—C15—Cl2	118.09 (18)
C7—C6—H6	125.3
C9—O1—C4—C3	177.01 (19)	C3—C4—C5—C8	−113.9 (3)
C9—O1—C4—C5	−61.7 (3)	O2—C5—C8—C7	0.9 (4)
C4—O1—C9—C10	−171.48 (18)	C4—C5—C8—C7	178.2 (3)
C6—O2—C5—C4	−178.8 (2)	C8—C7—C6—O2	−0.2 (4)
C6—O2—C5—C8	−1.0 (3)	C5—C8—C7—C6	−0.4 (4)
C5—O2—C6—C7	0.8 (3)	C11—C10—C9—O1	2.1 (3)
C2—N1—N2—C1	0.4 (3)	C15—C10—C9—O1	−177.9 (2)
C3—N1—N2—C1	178.7 (2)	C9—C10—C11—C12	178.9 (2)
N2—N1—C2—N3	−0.9 (3)	C15—C10—C11—C12	−1.1 (4)
C3—N1—C2—N3	−179.0 (2)	C9—C10—C15—Cl2	−0.3 (3)
N2—N1—C3—C4	−77.0 (3)	C9—C10—C15—C14	−178.6 (2)
C2—N1—C3—C4	100.9 (3)	C11—C10—C15—Cl2	179.67 (18)
N1—N2—C1—N3	0.2 (3)	C11—C10—C15—C14	1.4 (3)
C2—N3—C1—N2	−0.7 (3)	C10—C11—C12—C13	0.0 (4)
C1—N3—C2—N1	1.0 (3)	Cl1—C13—C12—C11	−176.9 (2)
O1—C4—C3—N1	−60.3 (3)	C14—C13—C12—C11	0.9 (4)
C5—C4—C3—N1	176.7 (2)	C15—C14—C13—Cl1	177.24 (18)
O1—C4—C5—O2	−55.2 (3)	C15—C14—C13—C12	−0.6 (4)
O1—C4—C5—C8	127.7 (3)	C13—C14—C15—C10	−0.6 (4)
C3—C4—C5—O2	63.3 (3)	C13—C14—C15—Cl2	−178.91 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1	0.93	2.35	2.702 (3)	102
C9—H9B···Cg1i	0.97	2.90	3.775 (3)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O1	0.93	2.35	2.702 (3)	102
C9—H9B⋯Cg1i	0.97	2.90	3.775 (3)	151

Symmetry code: (i) . Cg1 is the centroid of the C10—C15 ring.