(Z)-Methyl 2-bromo-methyl-3-(2-chloro-phen-yl)acrylate.

In the title compound, C(11)H(10)BrClO(2), the dihedral angle between the benzene ring and the plane of the acrylate unit is 62.1 (1)°. The crystal packing is stabilzed by inter-molecular C-H⋯O hydrogen bonds and C-Cl⋯π inter-actions [Cl⋯centroid = 3.829 (1) Å and C-Cl⋯centroid = 165.3 (1)°].

Related literature

For background to the applications of acrylates, see: de Fraine & Martin (1991 ▶); Zhang & Ji (1992 ▶). For related structures, see: Wang et al. (2011 ▶); Ren et al. (2008 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C11H10BrClO2

M = 289.55

Monoclinic,

a = 10.0657 (7) Å

b = 10.2174 (7) Å

c = 11.3598 (7) Å

β = 97.649 (2)°

V = 1157.91 (13) Å3

Z = 4

Mo Kα radiation

μ = 3.76 mm−1

T = 293 K

0.24 × 0.22 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.390, T max = 0.548

14580 measured reflections

3336 independent reflections

2139 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.089

S = 0.99

3336 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.57 e Å−3

Δρmin = −0.54 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811039663/kj2189sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039663/kj2189Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811039663/kj2189Isup3.cml

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

C11H10BrClO2	F(000) = 576
Mr = 289.55	Dx = 1.661 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3345 reflections
a = 10.0657 (7) Å	θ = 2.0–29.9°
b = 10.2174 (7) Å	µ = 3.76 mm−1
c = 11.3598 (7) Å	T = 293 K
β = 97.649 (2)°	Block, yellow
V = 1157.91 (13) Å3	0.24 × 0.22 × 0.16 mm
Z = 4

Bruker APEXII CCD diffractometer	3336 independent reflections
Radiation source: fine-focus sealed tube	2139 reflections with I > 2σ(I)
graphite	Rint = 0.034
Detector resolution: 10.0 pixels mm-1	θmax = 29.9°, θmin = 2.0°
ω scans	h = −14→14
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −14→14
Tmin = 0.390, Tmax = 0.548	l = −15→15
14580 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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0394P)2 + 0.4461P] where P = (Fo2 + 2Fc2)/3
3336 reflections	(Δ/σ)max = 0.001
137 parameters	Δρmax = 0.57 e Å−3
0 restraints	Δρmin = −0.54 e Å−3

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
Br1	0.83211 (3)	0.03430 (3)	0.63091 (2)	0.06228 (12)
Cl1	0.43126 (7)	0.24881 (8)	1.00168 (6)	0.06382 (19)
O2	0.91325 (15)	0.14097 (17)	1.01998 (13)	0.0471 (4)
C1	0.4117 (2)	0.1427 (2)	0.8812 (2)	0.0437 (5)
C6	0.5234 (2)	0.0869 (2)	0.84130 (19)	0.0391 (5)
C7	0.6602 (2)	0.1162 (2)	0.89910 (19)	0.0381 (5)
H7	0.6767	0.1091	0.9814	0.046*
C8	0.7621 (2)	0.1522 (2)	0.84211 (18)	0.0358 (4)
C10	0.8961 (2)	0.1833 (2)	0.90868 (18)	0.0387 (5)
O1	0.98111 (17)	0.2408 (2)	0.86463 (16)	0.0634 (5)
C9	0.7514 (2)	0.1773 (2)	0.71290 (19)	0.0439 (5)
H9A	0.7964	0.2589	0.6994	0.053*
H9B	0.6578	0.1863	0.6804	0.053*
C5	0.4999 (3)	0.0026 (2)	0.7449 (2)	0.0504 (6)
H5	0.5724	−0.0379	0.7171	0.061*
C2	0.2834 (2)	0.1184 (3)	0.8258 (2)	0.0552 (6)
H2	0.2102	0.1580	0.8533	0.066*
C3	0.2648 (3)	0.0354 (3)	0.7298 (3)	0.0602 (7)
H3	0.1786	0.0187	0.6922	0.072*
C11	1.0420 (2)	0.1709 (3)	1.0877 (2)	0.0585 (7)
H11A	1.1113	0.1245	1.0547	0.088*
H11B	1.0416	0.1447	1.1688	0.088*
H11C	1.0583	0.2633	1.0845	0.088*
C4	0.3727 (3)	−0.0228 (3)	0.6893 (3)	0.0576 (7)
H4	0.3599	−0.0792	0.6246	0.069*

	U11	U22	U33	U12	U13	U23
Br1	0.06623 (19)	0.0758 (2)	0.04610 (15)	−0.00412 (14)	0.01240 (12)	−0.01212 (13)
Cl1	0.0517 (4)	0.0854 (5)	0.0558 (4)	0.0079 (3)	0.0125 (3)	−0.0115 (3)
O2	0.0394 (8)	0.0644 (11)	0.0359 (8)	0.0020 (8)	−0.0008 (6)	−0.0001 (7)
C1	0.0385 (11)	0.0485 (14)	0.0449 (12)	0.0006 (10)	0.0091 (9)	0.0080 (10)
C6	0.0320 (10)	0.0409 (12)	0.0442 (11)	−0.0023 (9)	0.0042 (8)	0.0075 (10)
C7	0.0343 (10)	0.0416 (13)	0.0381 (10)	0.0038 (9)	0.0032 (8)	0.0036 (9)
C8	0.0309 (10)	0.0375 (12)	0.0383 (10)	0.0040 (9)	0.0023 (8)	0.0034 (9)
C10	0.0333 (10)	0.0448 (13)	0.0380 (10)	0.0053 (9)	0.0053 (8)	−0.0013 (9)
O1	0.0381 (9)	0.0980 (15)	0.0530 (10)	−0.0153 (9)	0.0023 (7)	0.0131 (10)
C9	0.0365 (11)	0.0537 (14)	0.0406 (11)	0.0007 (10)	0.0015 (9)	0.0071 (10)
C5	0.0447 (13)	0.0450 (14)	0.0617 (15)	−0.0032 (11)	0.0073 (11)	−0.0004 (11)
C2	0.0329 (11)	0.0706 (18)	0.0627 (15)	0.0017 (12)	0.0087 (10)	0.0129 (14)
C3	0.0400 (13)	0.0667 (18)	0.0700 (17)	−0.0132 (13)	−0.0064 (12)	0.0111 (14)
C11	0.0447 (13)	0.082 (2)	0.0447 (13)	0.0099 (13)	−0.0091 (10)	−0.0104 (13)
C4	0.0533 (15)	0.0524 (16)	0.0642 (16)	−0.0124 (13)	−0.0026 (12)	−0.0010 (13)

Br1—C9	1.966 (2)	C9—H9A	0.9700
Cl1—C1	1.737 (3)	C9—H9B	0.9700
O2—C10	1.326 (3)	C5—C4	1.375 (4)
O2—C11	1.449 (3)	C5—H5	0.9300
C1—C2	1.381 (3)	C2—C3	1.375 (4)
C1—C6	1.389 (3)	C2—H2	0.9300
C6—C5	1.389 (4)	C3—C4	1.371 (4)
C6—C7	1.475 (3)	C3—H3	0.9300
C7—C8	1.336 (3)	C11—H11A	0.9600
C7—H7	0.9300	C11—H11B	0.9600
C8—C9	1.480 (3)	C11—H11C	0.9600
C8—C10	1.490 (3)	C4—H4	0.9300
C10—O1	1.201 (3)
C10—O2—C11	115.55 (19)	Br1—C9—H9B	109.4
C2—C1—C6	121.7 (2)	H9A—C9—H9B	108.0
C2—C1—Cl1	118.14 (19)	C4—C5—C6	121.9 (3)
C6—C1—Cl1	120.10 (18)	C4—C5—H5	119.0
C1—C6—C5	116.9 (2)	C6—C5—H5	119.0
C1—C6—C7	121.3 (2)	C3—C2—C1	119.5 (2)
C5—C6—C7	121.8 (2)	C3—C2—H2	120.3
C8—C7—C6	124.9 (2)	C1—C2—H2	120.3
C8—C7—H7	117.6	C4—C3—C2	120.2 (2)
C6—C7—H7	117.6	C4—C3—H3	119.9
C7—C8—C9	124.71 (19)	C2—C3—H3	119.9
C7—C8—C10	120.97 (19)	O2—C11—H11A	109.5
C9—C8—C10	114.06 (18)	O2—C11—H11B	109.5
O1—C10—O2	123.2 (2)	H11A—C11—H11B	109.5
O1—C10—C8	122.7 (2)	O2—C11—H11C	109.5
O2—C10—C8	114.11 (18)	H11A—C11—H11C	109.5
C8—C9—Br1	111.16 (15)	H11B—C11—H11C	109.5
C8—C9—H9A	109.4	C3—C4—C5	119.7 (3)
Br1—C9—H9A	109.4	C3—C4—H4	120.2
C8—C9—H9B	109.4	C5—C4—H4	120.2
C2—C1—C6—C5	−1.7 (3)	C7—C8—C10—O2	16.2 (3)
Cl1—C1—C6—C5	179.72 (18)	C9—C8—C10—O2	−169.36 (19)
C2—C1—C6—C7	178.3 (2)	C7—C8—C9—Br1	−106.0 (2)
Cl1—C1—C6—C7	−0.2 (3)	C10—C8—C9—Br1	79.8 (2)
C1—C6—C7—C8	−130.5 (2)	C1—C6—C5—C4	1.4 (4)
C5—C6—C7—C8	49.6 (3)	C7—C6—C5—C4	−178.6 (2)
C6—C7—C8—C9	4.5 (4)	C6—C1—C2—C3	1.1 (4)
C6—C7—C8—C10	178.3 (2)	Cl1—C1—C2—C3	179.6 (2)
C11—O2—C10—O1	1.2 (3)	C1—C2—C3—C4	0.0 (4)
C11—O2—C10—C8	−179.3 (2)	C2—C3—C4—C5	−0.3 (4)
C7—C8—C10—O1	−164.3 (2)	C6—C5—C4—C3	−0.5 (4)
C9—C8—C10—O1	10.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O2	0.93	2.39	2.740 (3)	102
C2—H2···O1i	0.93	2.48	3.373 (3)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.93	2.48	3.373 (3)	162

Symmetry code: (i) .