Imaza-lil: 1-[2-(2,4-dichloro-phen-yl)-2-(prop-2-en-yloxy)eth-yl]-1H-imidazole.

In the title compound, C(14)H(14)Cl(2)N(2)O, the imidazole ring is almost parallel to the benzene ring, the dihedral angle between them being 7.3 (2)°. In the crystal, there is an inter-molecular C-Cl⋯π inter-action (Cl⋯centroid = 3.36 Å and C-Cl⋯centroid = 89.2°). In addition, a Cl⋯Cl contact of 3.411 (1) Å and an inter-molecular C-H⋯N hydrogen bond are observed. These inter-actions contribute to the stabilization of the crystal packing.

Related literature

For information on the toxicity of the title compound, see: Sisman & Türkez (2010 ▶). For related structures, see: Bisaha et al. (2005 ▶).

Experimental

Crystal data

C14H14Cl2N2O

M = 297.17

Monoclinic,

a = 7.9374 (6) Å

b = 13.4144 (12) Å

c = 13.479 (1) Å

β = 103.386 (5)°

V = 1396.19 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.46 mm−1

T = 173 K

0.20 × 0.09 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.914, T max = 0.964

12201 measured reflections

3040 independent reflections

2282 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.119

S = 1.08

3040 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811018241/wn2433sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018241/wn2433Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811018241/wn2433Isup3.cml

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

C14H14Cl2N2O	F(000) = 616
Mr = 297.17	Dx = 1.414 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2420 reflections
a = 7.9374 (6) Å	θ = 2.2–28.4°
b = 13.4144 (12) Å	µ = 0.46 mm−1
c = 13.479 (1) Å	T = 173 K
β = 103.386 (5)°	Plate, colourless
V = 1396.19 (19) Å3	0.20 × 0.09 × 0.08 mm
Z = 4

Bruker APEXII CCD diffractometer	3040 independent reflections
Radiation source: fine-focus sealed tube	2282 reflections with I > 2σ(I)
graphite	Rint = 0.069
φ and ω scans	θmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→10
Tmin = 0.914, Tmax = 0.964	k = −17→14
12201 measured reflections	l = −17→17

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0525P)2 + 0.2498P] where P = (Fo2 + 2Fc2)/3
3040 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.27 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	0.41595 (8)	0.69956 (5)	0.57733 (5)	0.0410 (2)
Cl2	0.77994 (7)	0.98990 (4)	0.47431 (5)	0.03569 (19)
O1	0.0431 (2)	0.71310 (11)	0.25901 (12)	0.0294 (4)
N1	−0.1440 (2)	0.69576 (14)	0.40437 (15)	0.0289 (4)
N2	−0.3936 (3)	0.60867 (17)	0.34432 (19)	0.0465 (6)
C1	0.4327 (3)	0.78309 (16)	0.48568 (17)	0.0282 (5)
C2	0.5822 (3)	0.84344 (16)	0.51200 (18)	0.0285 (5)
H2	0.6668	0.8363	0.5742	0.034*
C3	0.5937 (3)	0.91175 (16)	0.44116 (18)	0.0279 (5)
C4	0.4636 (3)	0.91953 (16)	0.34627 (18)	0.0297 (5)
H4	0.4775	0.9689	0.2982	0.036*
C5	0.3172 (3)	0.85669 (16)	0.32241 (18)	0.0277 (5)
H5	0.2343	0.8632	0.2594	0.033*
C6	0.2977 (3)	0.78727 (15)	0.39102 (17)	0.0255 (5)
C7	0.1325 (3)	0.72205 (16)	0.36550 (17)	0.0253 (5)
H7	0.1605	0.6540	0.3949	0.030*
C8	−0.0025 (3)	0.76633 (17)	0.40885 (19)	0.0311 (5)
H8A	0.0469	0.7854	0.4806	0.037*
H8B	−0.0474	0.8274	0.3704	0.037*
C9	−0.3009 (3)	0.68361 (19)	0.3287 (2)	0.0377 (6)
H9	−0.3345	0.7269	0.2718	0.045*
C10	−0.2883 (4)	0.5710 (2)	0.4355 (2)	0.0505 (7)
H10	−0.3197	0.5139	0.4688	0.061*
C11	−0.1353 (4)	0.6230 (2)	0.4733 (2)	0.0440 (6)
H11	−0.0471	0.6102	0.5328	0.053*
C12	0.1149 (3)	0.63442 (17)	0.21546 (18)	0.0312 (5)
H12A	0.2426	0.6410	0.2344	0.037*
H12B	0.0777	0.6401	0.1403	0.037*
C13	0.0682 (3)	0.53464 (18)	0.24568 (19)	0.0350 (6)
H13	−0.0508	0.5167	0.2311	0.042*
C14	0.1862 (4)	0.4672 (2)	0.2933 (2)	0.0451 (7)
H14B	0.3060	0.4833	0.3087	0.054*
H14A	0.1493	0.4037	0.3112	0.054*

	U11	U22	U33	U12	U13	U23
Cl1	0.0519 (4)	0.0404 (4)	0.0294 (3)	−0.0131 (3)	0.0066 (3)	0.0096 (3)
Cl2	0.0339 (3)	0.0338 (3)	0.0442 (4)	−0.0075 (2)	0.0189 (3)	−0.0031 (3)
O1	0.0340 (8)	0.0319 (8)	0.0244 (8)	0.0010 (7)	0.0111 (7)	−0.0023 (7)
N1	0.0320 (10)	0.0296 (10)	0.0285 (10)	0.0003 (8)	0.0139 (9)	−0.0005 (8)
N2	0.0390 (12)	0.0524 (14)	0.0515 (15)	−0.0104 (11)	0.0170 (11)	−0.0142 (12)
C1	0.0376 (12)	0.0253 (11)	0.0253 (12)	0.0009 (10)	0.0147 (10)	0.0020 (9)
C2	0.0310 (12)	0.0305 (12)	0.0256 (12)	0.0001 (10)	0.0098 (10)	−0.0012 (10)
C3	0.0286 (11)	0.0249 (11)	0.0347 (13)	−0.0021 (9)	0.0168 (10)	−0.0065 (10)
C4	0.0362 (12)	0.0251 (11)	0.0337 (13)	0.0022 (9)	0.0203 (11)	0.0035 (10)
C5	0.0305 (12)	0.0288 (12)	0.0256 (12)	0.0033 (9)	0.0104 (10)	0.0002 (10)
C6	0.0315 (12)	0.0233 (11)	0.0253 (11)	0.0030 (9)	0.0142 (10)	−0.0022 (9)
C7	0.0313 (11)	0.0236 (11)	0.0225 (11)	−0.0007 (9)	0.0090 (10)	−0.0019 (9)
C8	0.0399 (13)	0.0259 (12)	0.0324 (13)	−0.0017 (10)	0.0183 (11)	−0.0032 (10)
C9	0.0362 (13)	0.0440 (14)	0.0357 (14)	0.0031 (11)	0.0136 (12)	−0.0004 (12)
C10	0.0503 (16)	0.0398 (15)	0.066 (2)	−0.0085 (13)	0.0237 (16)	0.0085 (14)
C11	0.0441 (15)	0.0475 (15)	0.0410 (15)	−0.0023 (12)	0.0109 (13)	0.0163 (13)
C12	0.0367 (13)	0.0334 (12)	0.0277 (12)	−0.0062 (10)	0.0159 (11)	−0.0058 (10)
C13	0.0403 (13)	0.0357 (13)	0.0319 (13)	−0.0111 (11)	0.0143 (11)	−0.0077 (11)
C14	0.0631 (18)	0.0383 (14)	0.0387 (15)	−0.0040 (13)	0.0219 (14)	−0.0038 (12)

Cl1—C1	1.696 (2)	C5—H5	0.9500
Cl2—C3	1.783 (2)	C6—C7	1.547 (3)
O1—C12	1.392 (3)	C7—C8	1.461 (3)
O1—C7	1.452 (3)	C7—H7	1.0000
N1—C11	1.338 (3)	C8—H8A	0.9900
N1—C9	1.425 (3)	C8—H8B	0.9900
N1—C8	1.459 (3)	C9—H9	0.9500
N2—C9	1.291 (3)	C10—C11	1.391 (4)
N2—C10	1.410 (4)	C10—H10	0.9500
C1—C2	1.412 (3)	C11—H11	0.9500
C1—C6	1.465 (3)	C12—C13	1.471 (3)
C2—C3	1.342 (3)	C12—H12A	0.9900
C2—H2	0.9500	C12—H12B	0.9900
C3—C4	1.450 (3)	C13—C14	1.353 (4)
C4—C5	1.411 (3)	C13—H13	0.9500
C4—H4	0.9500	C14—H14B	0.9500
C5—C6	1.346 (3)	C14—H14A	0.9500
C12—O1—C7	108.98 (17)	C6—C7—H7	109.2
C11—N1—C9	108.0 (2)	N1—C8—C7	110.39 (18)
C11—N1—C8	121.9 (2)	N1—C8—H8A	109.6
C9—N1—C8	129.8 (2)	C7—C8—H8A	109.6
C9—N2—C10	100.1 (2)	N1—C8—H8B	109.6
C2—C1—C6	126.8 (2)	C7—C8—H8B	109.6
C2—C1—Cl1	113.51 (18)	H8A—C8—H8B	108.1
C6—C1—Cl1	119.65 (16)	N2—C9—N1	114.1 (2)
C3—C2—C1	113.9 (2)	N2—C9—H9	122.9
C3—C2—H2	123.1	N1—C9—H9	122.9
C1—C2—H2	123.1	C11—C10—N2	115.5 (2)
C2—C3—C4	121.7 (2)	C11—C10—H10	122.2
C2—C3—Cl2	114.37 (18)	N2—C10—H10	122.2
C4—C3—Cl2	123.96 (17)	N1—C11—C10	102.2 (2)
C5—C4—C3	122.6 (2)	N1—C11—H11	128.9
C5—C4—H4	118.7	C10—C11—H11	128.9
C3—C4—H4	118.7	O1—C12—C13	114.76 (18)
C6—C5—C4	118.4 (2)	O1—C12—H12A	108.6
C6—C5—H5	120.8	C13—C12—H12A	108.6
C4—C5—H5	120.8	O1—C12—H12B	108.6
C5—C6—C1	116.6 (2)	C13—C12—H12B	108.6
C5—C6—C7	117.7 (2)	H12A—C12—H12B	107.6
C1—C6—C7	125.69 (19)	C14—C13—C12	123.3 (2)
O1—C7—C8	101.13 (18)	C14—C13—H13	118.4
O1—C7—C6	117.51 (17)	C12—C13—H13	118.4
C8—C7—C6	110.10 (17)	C13—C14—H14B	120.0
O1—C7—H7	109.2	C13—C14—H14A	120.0
C8—C7—H7	109.2	H14B—C14—H14A	120.0
C6—C1—C2—C3	1.4 (3)	C1—C6—C7—O1	−160.79 (18)
Cl1—C1—C2—C3	−178.10 (16)	C5—C6—C7—C8	−93.1 (2)
C1—C2—C3—C4	−1.0 (3)	C1—C6—C7—C8	84.2 (3)
C1—C2—C3—Cl2	179.00 (15)	C11—N1—C8—C7	80.7 (3)
C2—C3—C4—C5	0.3 (3)	C9—N1—C8—C7	−93.6 (3)
Cl2—C3—C4—C5	−179.78 (16)	O1—C7—C8—N1	67.1 (2)
C3—C4—C5—C6	0.4 (3)	C6—C7—C8—N1	−167.88 (18)
C4—C5—C6—C1	−0.1 (3)	C10—N2—C9—N1	−0.1 (3)
C4—C5—C6—C7	177.48 (18)	C11—N1—C9—N2	0.2 (3)
C2—C1—C6—C5	−0.8 (3)	C8—N1—C9—N2	175.2 (2)
Cl1—C1—C6—C5	178.64 (16)	C9—N2—C10—C11	0.0 (3)
C2—C1—C6—C7	−178.2 (2)	C9—N1—C11—C10	−0.2 (3)
Cl1—C1—C6—C7	1.3 (3)	C8—N1—C11—C10	−175.6 (2)
C12—O1—C7—C8	−152.67 (17)	N2—C10—C11—N1	0.2 (3)
C12—O1—C7—C6	87.5 (2)	C7—O1—C12—C13	73.9 (2)
C5—C6—C7—O1	21.8 (3)	O1—C12—C13—C14	−120.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···N2i	0.95	2.66	3.562 (3)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯N2i	0.95	2.66	3.562 (3)	159

Symmetry code: (i) .