1-[2-(2,6-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 2.54 (13) and 44.43 (12)°, respectively with respect to the furan and dichloro-benzene rings. The dihedral angle between the dichloro-benzene and furan rings is 46.75 (12)°. In the crystal structure, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric dimers and π-π contacts between dichloro-benzene rings [centroid-centroid distance = 3.583 (2) Å] may further stabilize the structure. Inter-molecular C-H⋯π contacts between the triazole and furan rings also occur.

Related literature

For general background to 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 ▶); Özel Güven et al. (2009 ▶); Peeters et al. (1979 ▶).

Experimental

Crystal data

C15H13Cl2N3O2

M = 338.18

Monoclinic,

a = 10.5853 (3) Å

b = 12.4960 (2) Å

c = 12.5850 (3) Å

β = 114.455 (1)°

V = 1515.32 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.44 mm−1

T = 120 K

0.40 × 0.40 × 0.10 mm

Data collection

Bruker–Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.837, T max = 0.955

33067 measured reflections

3438 independent reflections

2775 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.180

S = 1.04

3438 reflections

200 parameters

H-atom parameters constrained

Δρmax = 1.20 e Å−3

Δρmin = −0.76 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809052568/xu2704sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809052568/xu2704Isup2.hkl

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

C15H13Cl2N3O2	F(000) = 696
Mr = 338.18	Dx = 1.482 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 23020 reflections
a = 10.5853 (3) Å	θ = 2.9–27.5°
b = 12.4960 (2) Å	µ = 0.44 mm−1
c = 12.5850 (3) Å	T = 120 K
β = 114.455 (1)°	Plate, colorless
V = 1515.32 (6) Å3	0.40 × 0.40 × 0.10 mm
Z = 4

Bruker–Nonius KappaCCD diffractometer	3438 independent reflections
Radiation source: fine-focus sealed tube	2775 reflections with I > 2σ(I)
graphite	Rint = 0.058
φ and ω scans	θmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −13→13
Tmin = 0.837, Tmax = 0.955	k = −14→15
33067 measured reflections	l = −16→16

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)] = 0.067	H-atom parameters constrained
wR(F2) = 0.180	w = 1/[σ2(Fo2) + (0.0984P)2 + 1.9705P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3438 reflections	Δρmax = 1.20 e Å−3
200 parameters	Δρmin = −0.76 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: 0.051 (5)

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 > 2sigma(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	0.32066 (8)	0.66344 (7)	1.08482 (8)	0.0470 (3)
Cl2	0.29005 (8)	0.31220 (7)	0.82358 (9)	0.0497 (3)
O1	0.07950 (17)	0.54757 (14)	0.86960 (15)	0.0231 (4)
O2	−0.1088 (3)	0.5914 (2)	0.5685 (2)	0.0483 (6)
N1	−0.0576 (2)	0.71549 (17)	0.93071 (19)	0.0226 (5)
N2	−0.0121 (2)	0.81516 (18)	0.9183 (2)	0.0284 (5)
N3	0.0458 (2)	0.7770 (2)	1.1089 (2)	0.0298 (5)
C1	0.0483 (3)	0.8475 (2)	1.0282 (3)	0.0300 (6)
H1	0.0898	0.9144	1.0487	0.036*
C2	−0.0207 (3)	0.6947 (2)	1.0435 (2)	0.0255 (5)
H2	−0.0393	0.6309	1.0724	0.031*
C3	−0.1260 (3)	0.6463 (2)	0.8301 (2)	0.0248 (5)
H3A	−0.2023	0.6846	0.7706	0.030*
H3B	−0.1638	0.5842	0.8530	0.030*
C4	−0.0241 (2)	0.6098 (2)	0.7800 (2)	0.0228 (5)
H4	0.0197	0.6727	0.7628	0.027*
C5	−0.0952 (3)	0.5454 (2)	0.6705 (2)	0.0250 (5)
C6	−0.1805 (4)	0.5198 (4)	0.4817 (3)	0.0582 (11)
H6	−0.2048	0.5311	0.4026	0.070*
C7	−0.2101 (3)	0.4328 (3)	0.5259 (3)	0.0457 (9)
H7	−0.2564	0.3726	0.4847	0.055*
C8	−0.1574 (3)	0.4484 (3)	0.6500 (3)	0.0429 (8)
H8	−0.1646	0.4016	0.7047	0.051*
C9	0.2081 (3)	0.5444 (2)	0.8579 (2)	0.0244 (5)
H9A	0.2416	0.6164	0.8565	0.029*
H9B	0.1961	0.5086	0.7859	0.029*
C10	0.3091 (2)	0.4839 (2)	0.9611 (2)	0.0224 (5)
C11	0.3640 (3)	0.5315 (2)	1.0718 (2)	0.0283 (6)
C12	0.4517 (3)	0.4781 (3)	1.1713 (3)	0.0424 (8)
H12	0.4849	0.5122	1.2435	0.051*
C13	0.4890 (3)	0.3753 (3)	1.1629 (3)	0.0459 (9)
H13	0.5469	0.3388	1.2297	0.055*
C14	0.4416 (3)	0.3250 (2)	1.0558 (4)	0.0427 (9)
H14	0.4695	0.2555	1.0500	0.051*
C15	0.3507 (3)	0.3794 (2)	0.9559 (3)	0.0304 (6)

	U11	U22	U33	U12	U13	U23
Cl1	0.0272 (4)	0.0521 (5)	0.0535 (5)	0.0023 (3)	0.0085 (3)	−0.0273 (4)
Cl2	0.0340 (4)	0.0412 (5)	0.0711 (6)	−0.0067 (3)	0.0191 (4)	−0.0283 (4)
O1	0.0144 (8)	0.0260 (9)	0.0257 (9)	0.0012 (6)	0.0052 (7)	0.0068 (7)
O2	0.0633 (16)	0.0525 (15)	0.0306 (12)	−0.0134 (12)	0.0208 (11)	−0.0054 (10)
N1	0.0183 (10)	0.0227 (11)	0.0247 (11)	−0.0008 (8)	0.0069 (8)	0.0013 (8)
N2	0.0284 (12)	0.0243 (12)	0.0289 (12)	−0.0032 (9)	0.0082 (9)	0.0016 (9)
N3	0.0262 (11)	0.0356 (13)	0.0269 (12)	0.0010 (10)	0.0105 (9)	−0.0031 (9)
C1	0.0244 (13)	0.0283 (14)	0.0341 (15)	−0.0025 (10)	0.0089 (11)	−0.0028 (11)
C2	0.0228 (12)	0.0282 (13)	0.0282 (13)	0.0003 (10)	0.0131 (11)	0.0020 (10)
C3	0.0172 (11)	0.0250 (13)	0.0271 (13)	−0.0020 (9)	0.0041 (10)	−0.0012 (10)
C4	0.0168 (11)	0.0230 (12)	0.0233 (12)	0.0005 (9)	0.0032 (9)	0.0040 (9)
C5	0.0201 (12)	0.0264 (13)	0.0247 (13)	0.0046 (9)	0.0057 (10)	0.0000 (10)
C6	0.065 (3)	0.077 (3)	0.0307 (17)	−0.009 (2)	0.0176 (17)	−0.0201 (17)
C7	0.0299 (15)	0.0392 (18)	0.051 (2)	0.0080 (13)	−0.0004 (14)	−0.0203 (15)
C8	0.0333 (16)	0.0322 (16)	0.0470 (19)	−0.0052 (12)	0.0004 (14)	0.0062 (13)
C9	0.0177 (11)	0.0308 (13)	0.0254 (13)	0.0016 (9)	0.0096 (10)	0.0038 (10)
C10	0.0152 (11)	0.0240 (12)	0.0286 (13)	0.0001 (9)	0.0095 (10)	0.0050 (10)
C11	0.0165 (11)	0.0400 (15)	0.0289 (14)	0.0013 (10)	0.0098 (10)	0.0039 (11)
C12	0.0208 (13)	0.080 (3)	0.0261 (15)	0.0038 (14)	0.0098 (12)	0.0119 (15)
C13	0.0222 (14)	0.068 (2)	0.0461 (19)	0.0056 (14)	0.0131 (13)	0.0354 (17)
C14	0.0233 (14)	0.0281 (15)	0.080 (3)	0.0056 (11)	0.0243 (16)	0.0228 (15)
C15	0.0190 (12)	0.0248 (13)	0.0472 (17)	−0.0040 (10)	0.0134 (12)	−0.0008 (11)

N1—N2	1.367 (3)	C7—C8	1.438 (5)
C1—N2	1.324 (4)	C7—H7	0.9300
C1—N3	1.352 (4)	C8—H8	0.9300
C1—H1	0.9300	C9—O1	1.429 (3)
C2—N3	1.323 (4)	C9—H9A	0.9700
C2—N1	1.333 (3)	C9—H9B	0.9700
C2—H2	0.9300	C10—C9	1.501 (3)
C3—N1	1.455 (3)	C10—C11	1.401 (4)
C3—H3A	0.9700	C10—C15	1.389 (4)
C3—H3B	0.9700	C11—Cl1	1.737 (3)
C4—O1	1.434 (3)	C11—C12	1.383 (4)
C4—C3	1.527 (4)	C12—C13	1.361 (6)
C4—C5	1.501 (4)	C12—H12	0.9300
C4—H4	0.9800	C13—C14	1.380 (6)
C5—O2	1.359 (4)	C13—H13	0.9300
C5—C8	1.352 (4)	C14—C15	1.403 (4)
C6—O2	1.373 (4)	C14—H14	0.9300
C6—C7	1.317 (6)	C15—Cl2	1.733 (3)
C6—H6	0.9300
C9—O1—C4	112.62 (18)	C6—C7—C8	107.1 (3)
C5—O2—C6	106.5 (3)	C6—C7—H7	126.5
N2—N1—C3	120.9 (2)	C8—C7—H7	126.5
C2—N1—N2	109.7 (2)	C5—C8—C7	105.6 (3)
C2—N1—C3	129.2 (2)	C5—C8—H8	127.2
C1—N2—N1	101.5 (2)	C7—C8—H8	127.2
C2—N3—C1	102.1 (2)	O1—C9—C10	107.01 (19)
N2—C1—N3	115.7 (2)	O1—C9—H9A	110.3
N2—C1—H1	122.1	O1—C9—H9B	110.3
N3—C1—H1	122.1	C10—C9—H9A	110.3
N1—C2—H2	124.5	C10—C9—H9B	110.3
N3—C2—N1	110.9 (2)	H9A—C9—H9B	108.6
N3—C2—H2	124.5	C11—C10—C9	120.1 (2)
N1—C3—C4	110.8 (2)	C15—C10—C9	124.0 (2)
N1—C3—H3A	109.5	C15—C10—C11	115.9 (2)
N1—C3—H3B	109.5	C10—C11—Cl1	118.7 (2)
C4—C3—H3A	109.5	C12—C11—C10	122.9 (3)
C4—C3—H3B	109.5	C12—C11—Cl1	118.5 (3)
H3A—C3—H3B	108.1	C11—C12—H12	120.3
O1—C4—C3	106.1 (2)	C13—C12—C11	119.5 (3)
O1—C4—C5	111.1 (2)	C13—C12—H12	120.3
O1—C4—H4	109.3	C12—C13—C14	120.5 (3)
C3—C4—H4	109.3	C12—C13—H13	119.8
C5—C4—C3	111.5 (2)	C14—C13—H13	119.8
C5—C4—H4	109.3	C13—C14—C15	119.5 (3)
O2—C5—C4	117.2 (2)	C13—C14—H14	120.3
C8—C5—O2	110.3 (3)	C15—C14—H14	120.3
C8—C5—C4	132.5 (3)	C10—C15—Cl2	120.2 (2)
O2—C6—H6	124.7	C10—C15—C14	121.8 (3)
C7—C6—O2	110.6 (3)	C14—C15—Cl2	118.1 (2)
C7—C6—H6	124.7
C2—N1—N2—C1	−1.0 (3)	C7—C6—O2—C5	−0.4 (4)
C3—N1—N2—C1	−176.9 (2)	O2—C6—C7—C8	1.3 (4)
N3—C1—N2—N1	0.4 (3)	C6—C7—C8—C5	−1.7 (4)
N2—C1—N3—C2	0.3 (3)	C10—C9—O1—C4	176.0 (2)
N3—C2—N1—N2	1.3 (3)	C11—C10—C9—O1	−73.1 (3)
N3—C2—N1—C3	176.7 (2)	C15—C10—C9—O1	104.8 (3)
N1—C2—N3—C1	−1.0 (3)	C9—C10—C11—Cl1	−3.8 (3)
C4—C3—N1—C2	−107.0 (3)	C9—C10—C11—C12	176.5 (2)
C4—C3—N1—N2	68.0 (3)	C15—C10—C11—Cl1	178.21 (19)
C3—C4—O1—C9	−156.0 (2)	C15—C10—C11—C12	−1.5 (4)
C5—C4—O1—C9	82.6 (3)	C9—C10—C15—Cl2	2.2 (3)
O1—C4—C3—N1	63.3 (3)	C9—C10—C15—C14	−177.5 (2)
C5—C4—C3—N1	−175.5 (2)	C11—C10—C15—Cl2	−179.85 (19)
O1—C4—C5—O2	−132.0 (2)	C11—C10—C15—C14	0.4 (4)
O1—C4—C5—C8	51.7 (4)	C10—C11—C12—C13	0.9 (4)
C3—C4—C5—O2	109.7 (3)	Cl1—C11—C12—C13	−178.8 (2)
C3—C4—C5—C8	−66.6 (4)	C11—C12—C13—C14	0.9 (4)
C4—C5—O2—C6	−177.9 (3)	C12—C13—C14—C15	−2.0 (4)
C8—C5—O2—C6	−0.8 (4)	C13—C14—C15—Cl2	−178.4 (2)
O2—C5—C8—C7	1.5 (4)	C13—C14—C15—C10	1.3 (4)
C4—C5—C8—C7	178.0 (3)

Cg1 and Cg2 are the centroids of the N1–N3/C1/C2 and O2/C5–C8 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1i	0.93	2.44	3.363 (3)	173
C9—H9B···Cl2	0.97	2.62	3.109 (3)	112
C1—H1···Cg2ii	0.93	2.79	3.488 (4)	133
C7—H7···Cg1iii	0.93	2.93	3.570 (4)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.93	2.44	3.363 (3)	173
C9—H9B⋯Cl2	0.97	2.62	3.109 (3)	112
C1—H1⋯Cg2ii	0.93	2.79	3.488 (4)	133
C7—H7⋯Cg1iii	0.93	2.93	3.570 (4)	127

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 and Cg2 are the centroids of the N1–N3/C1/C2 and O2/C5–C8 rings, respectively.