Methyl (2Z)-2-bromo-meth-yl-3-(3-chloro-phen-yl)prop-2-enoate.

There are two independent mol-ecules (A and B) in the asymmetric unit of the title compound C11H10BrClO2, which represents the Z isomer. The methyl-acrylate moieties are essentially planar, within 0.084 (2) and 0.027 (5) Å in mol-ecules A and B, respectively. The benzene ring makes dihedral angles of 13.17 (7) and 27.89 (9)° with the methyl-acrylate moiety in mol-ecules A and B, respectively. The methyl-bromide moiety is almost orthogonal to the benzene ring, making dihedral angles of 81.46 (16)° in mol-ecule A and 79.61 (16)° in mol-ecule B. The methyl-acrylate moiety exhibits an extended trans conformation in both mol-ecules. In the crystal, pairs of C-H⋯O hydrogen bonds result in the formation of quasi-centrosymmetric R 2 (2)(14) AB dimers.

Related literature

For the uses of cinnamic acid and its derivatives, see: De et al. (2011 ▶); Sharma (2011 ▶). For an extended acrylate conformation, see: Schweizer & Dunitz (1982 ▶). For a related structure, see: Swaminathan et al. (2013 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶)

Experimental

Crystal data

C11H10BrClO2

M = 289.54

Triclinic,

a = 7.4523 (3) Å

b = 11.7003 (4) Å

c = 14.3121 (5) Å

α = 72.078 (2)°

β = 76.539 (2)°

γ = 76.773 (2)°

V = 1137.98 (7) Å3

Z = 4

Mo Kα radiation

μ = 3.82 mm−1

T = 296 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.330, T max = 0.466

27124 measured reflections

6597 independent reflections

4205 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.092

S = 1.00

6597 reflections

273 parameters

H-atom parameters constrained

Δρmax = 0.85 e Å−3

Δρmin = −0.49 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813012117/ld2100sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813012117/ld2100Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813012117/ld2100Isup3.cml

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

C11H10BrClO2	Z = 4
Mr = 289.54	F(000) = 576
Triclinic, P1	Dx = 1.690 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4523 (3) Å	Cell parameters from 4205 reflections
b = 11.7003 (4) Å	θ = 2.7–30.0°
c = 14.3121 (5) Å	µ = 3.82 mm−1
α = 72.078 (2)°	T = 296 K
β = 76.539 (2)°	Block, colourless
γ = 76.773 (2)°	0.30 × 0.25 × 0.20 mm
V = 1137.98 (7) Å3

Bruker Kappa APEXII CCD diffractometer	6597 independent reflections
Radiation source: fine-focus sealed tube	4205 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
ω & φ scans	θmax = 30.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −10→8
Tmin = 0.330, Tmax = 0.466	k = −16→16
27124 measured reflections	l = −20→19

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0394P)2 + 0.4208P] where P = (Fo2 + 2Fc2)/3
6597 reflections	(Δ/σ)max < 0.001
273 parameters	Δρmax = 0.85 e Å−3
0 restraints	Δρmin = −0.49 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
C1A	0.2876 (3)	0.7438 (2)	0.31195 (17)	0.0375 (5)
H1A	0.3090	0.7571	0.3690	0.045*
C1B	0.7397 (3)	0.6245 (2)	0.15677 (18)	0.0427 (5)
H1B	0.7468	0.6413	0.2151	0.051*
C2A	0.2785 (3)	0.8381 (2)	0.22676 (18)	0.0427 (5)
C2B	0.7449 (3)	0.7153 (2)	0.06871 (19)	0.0471 (6)
C3A	0.2509 (4)	0.8220 (3)	0.14019 (19)	0.0520 (6)
H3A	0.2441	0.8869	0.0832	0.062*
C3B	0.7299 (4)	0.6945 (3)	−0.0185 (2)	0.0535 (7)
H3B	0.7325	0.7568	−0.0775	0.064*
C4A	0.2337 (4)	0.7075 (3)	0.13990 (19)	0.0535 (7)
H4A	0.2181	0.6947	0.0815	0.064*
C4B	0.7111 (4)	0.5795 (3)	−0.0165 (2)	0.0622 (8)
H4B	0.7003	0.5643	−0.0748	0.075*
C5A	0.2392 (4)	0.6116 (2)	0.22469 (17)	0.0449 (6)
H5A	0.2258	0.5351	0.2232	0.054*
C5B	0.7082 (4)	0.4864 (3)	0.07061 (18)	0.0515 (6)
H5B	0.6956	0.4092	0.0705	0.062*
C6A	0.2651 (3)	0.6286 (2)	0.31333 (16)	0.0349 (5)
C6B	0.7240 (3)	0.5078 (2)	0.15876 (17)	0.0387 (5)
C7A	0.2722 (3)	0.5341 (2)	0.40719 (15)	0.0332 (5)
H7A	0.3350	0.5491	0.4501	0.040*
C7B	0.7119 (3)	0.4161 (2)	0.25545 (17)	0.0362 (5)
H7B	0.6619	0.4469	0.3105	0.043*
C8A	0.2045 (3)	0.42983 (19)	0.44251 (15)	0.0322 (5)
C8B	0.7620 (3)	0.2947 (2)	0.27668 (17)	0.0357 (5)
C9A	0.2376 (3)	0.3555 (2)	0.54369 (16)	0.0345 (5)
C9B	0.7259 (3)	0.2279 (2)	0.38432 (18)	0.0400 (5)
C10A	0.2170 (4)	0.1673 (3)	0.6645 (2)	0.0570 (7)
H10A	0.3460	0.1550	0.6707	0.085*
H10B	0.1820	0.0900	0.6734	0.085*
H10C	0.1399	0.2051	0.7143	0.085*
C10B	0.7412 (6)	0.0366 (3)	0.5018 (2)	0.0936 (13)
H10D	0.8176	0.0562	0.5383	0.140*
H10E	0.7731	−0.0486	0.5051	0.140*
H10F	0.6116	0.0554	0.5303	0.140*
C11A	0.0906 (3)	0.3861 (2)	0.39206 (17)	0.0383 (5)
H11A	0.0254	0.4555	0.3480	0.046*
H11B	−0.0026	0.3441	0.4417	0.046*
C11B	0.8615 (3)	0.2251 (2)	0.20373 (19)	0.0462 (6)
H11C	0.9573	0.1618	0.2332	0.055*
H11D	0.9236	0.2794	0.1455	0.055*
O1A	0.2956 (3)	0.38962 (15)	0.60031 (12)	0.0480 (4)
O1B	0.6636 (3)	0.27411 (17)	0.45134 (13)	0.0552 (5)
O2A	0.1916 (2)	0.24515 (15)	0.56628 (12)	0.0459 (4)
O2B	0.7732 (3)	0.10769 (17)	0.39833 (14)	0.0643 (5)
Cl1A	0.30217 (12)	0.98211 (6)	0.22889 (6)	0.0646 (2)
Cl1B	0.76375 (14)	0.86058 (7)	0.06837 (6)	0.0776 (2)
Br1A	0.24789 (4)	0.27505 (2)	0.314378 (19)	0.04929 (9)
Br1B	0.69480 (5)	0.14955 (3)	0.16130 (2)	0.06111 (10)

	U11	U22	U33	U12	U13	U23
C1A	0.0424 (12)	0.0350 (13)	0.0363 (12)	−0.0070 (9)	−0.0090 (10)	−0.0092 (10)
C1B	0.0519 (14)	0.0411 (14)	0.0362 (13)	−0.0080 (11)	−0.0114 (10)	−0.0091 (11)
C2A	0.0468 (13)	0.0323 (13)	0.0462 (14)	−0.0061 (10)	−0.0112 (11)	−0.0048 (11)
C2B	0.0503 (14)	0.0406 (14)	0.0472 (15)	−0.0100 (11)	−0.0118 (11)	−0.0034 (12)
C3A	0.0648 (17)	0.0471 (16)	0.0375 (14)	−0.0092 (13)	−0.0129 (12)	0.0006 (12)
C3B	0.0583 (16)	0.0582 (18)	0.0349 (14)	−0.0101 (13)	−0.0069 (11)	−0.0004 (12)
C4A	0.0760 (18)	0.0533 (17)	0.0336 (13)	−0.0131 (14)	−0.0172 (12)	−0.0079 (12)
C4B	0.089 (2)	0.064 (2)	0.0360 (15)	−0.0127 (16)	−0.0175 (14)	−0.0123 (14)
C5A	0.0637 (15)	0.0401 (14)	0.0341 (13)	−0.0130 (12)	−0.0100 (11)	−0.0104 (11)
C5B	0.0742 (18)	0.0477 (16)	0.0380 (14)	−0.0128 (13)	−0.0145 (12)	−0.0139 (12)
C6A	0.0366 (11)	0.0365 (13)	0.0316 (11)	−0.0061 (9)	−0.0060 (9)	−0.0092 (10)
C6B	0.0420 (12)	0.0416 (14)	0.0335 (12)	−0.0084 (10)	−0.0078 (9)	−0.0097 (10)
C7A	0.0395 (11)	0.0313 (12)	0.0298 (11)	−0.0065 (9)	−0.0075 (9)	−0.0082 (9)
C7B	0.0410 (12)	0.0378 (13)	0.0323 (12)	−0.0108 (10)	−0.0070 (9)	−0.0096 (10)
C8A	0.0348 (11)	0.0355 (12)	0.0285 (11)	−0.0031 (9)	−0.0063 (9)	−0.0133 (10)
C8B	0.0356 (11)	0.0383 (13)	0.0366 (12)	−0.0089 (9)	−0.0074 (9)	−0.0123 (10)
C9A	0.0384 (11)	0.0318 (12)	0.0336 (12)	−0.0063 (9)	−0.0038 (9)	−0.0109 (10)
C9B	0.0486 (13)	0.0337 (13)	0.0403 (13)	−0.0108 (10)	−0.0143 (10)	−0.0064 (11)
C10A	0.0814 (19)	0.0398 (15)	0.0432 (15)	−0.0159 (14)	−0.0144 (14)	0.0049 (12)
C10B	0.176 (4)	0.0428 (18)	0.0502 (19)	−0.021 (2)	−0.019 (2)	0.0061 (15)
C11A	0.0401 (12)	0.0402 (13)	0.0383 (12)	−0.0075 (10)	−0.0080 (10)	−0.0145 (10)
C11B	0.0472 (13)	0.0444 (15)	0.0469 (14)	−0.0084 (11)	−0.0044 (11)	−0.0144 (12)
O1A	0.0712 (11)	0.0431 (10)	0.0357 (9)	−0.0166 (8)	−0.0183 (8)	−0.0075 (8)
O1B	0.0819 (13)	0.0480 (11)	0.0358 (9)	−0.0105 (9)	−0.0100 (9)	−0.0121 (8)
O2A	0.0687 (11)	0.0326 (9)	0.0382 (9)	−0.0164 (8)	−0.0133 (8)	−0.0037 (7)
O2B	0.1103 (17)	0.0354 (11)	0.0442 (11)	−0.0108 (10)	−0.0138 (10)	−0.0073 (9)
Cl1A	0.0915 (5)	0.0330 (4)	0.0676 (5)	−0.0149 (3)	−0.0219 (4)	−0.0024 (3)
Cl1B	0.1185 (7)	0.0414 (4)	0.0735 (5)	−0.0251 (4)	−0.0339 (5)	0.0048 (4)
Br1A	0.06512 (17)	0.04343 (16)	0.04765 (16)	−0.00739 (12)	−0.01453 (12)	−0.02202 (12)
Br1B	0.0890 (2)	0.05188 (18)	0.05424 (18)	−0.01782 (15)	−0.01588 (15)	−0.02436 (14)

C1A—C2A	1.373 (3)	C7A—H7A	0.9300
C1A—C6A	1.389 (3)	C7B—C8B	1.340 (3)
C1A—H1A	0.9300	C7B—H7B	0.9300
C1B—C2B	1.375 (3)	C8A—C11A	1.488 (3)
C1B—C6B	1.388 (3)	C8A—C9A	1.486 (3)
C1B—H1B	0.9300	C8B—C11B	1.480 (3)
C2A—C3A	1.376 (3)	C8B—C9B	1.489 (3)
C2A—Cl1A	1.743 (2)	C9A—O1A	1.202 (3)
C2B—C3B	1.376 (4)	C9A—O2A	1.335 (3)
C2B—Cl1B	1.736 (3)	C9B—O1B	1.194 (3)
C3A—C4A	1.375 (4)	C9B—O2B	1.333 (3)
C3A—H3A	0.9300	C10A—O2A	1.448 (3)
C3B—C4B	1.375 (4)	C10A—H10A	0.9600
C3B—H3B	0.9300	C10A—H10B	0.9600
C4A—C5A	1.378 (3)	C10A—H10C	0.9600
C4A—H4A	0.9300	C10B—O2B	1.452 (4)
C4B—C5B	1.380 (4)	C10B—H10D	0.9600
C4B—H4B	0.9300	C10B—H10E	0.9600
C5A—C6A	1.405 (3)	C10B—H10F	0.9600
C5A—H5A	0.9300	C11A—Br1A	1.971 (2)
C5B—C6B	1.395 (3)	C11A—H11A	0.9700
C5B—H5B	0.9300	C11A—H11B	0.9700
C6A—C7A	1.457 (3)	C11B—Br1B	1.969 (2)
C6B—C7B	1.465 (3)	C11B—H11C	0.9700
C7A—C8A	1.335 (3)	C11B—H11D	0.9700
C2A—C1A—C6A	120.3 (2)	C8B—C7B—H7B	115.1
C2A—C1A—H1A	119.9	C6B—C7B—H7B	115.1
C6A—C1A—H1A	119.9	C7A—C8A—C11A	125.72 (19)
C2B—C1B—C6B	120.1 (2)	C7A—C8A—C9A	116.34 (18)
C2B—C1B—H1B	119.9	C11A—C8A—C9A	117.84 (19)
C6B—C1B—H1B	119.9	C7B—C8B—C11B	125.4 (2)
C1A—C2A—C3A	121.8 (2)	C7B—C8B—C9B	115.7 (2)
C1A—C2A—Cl1A	118.87 (18)	C11B—C8B—C9B	118.7 (2)
C3A—C2A—Cl1A	119.3 (2)	O1A—C9A—O2A	123.0 (2)
C1B—C2B—C3B	121.5 (2)	O1A—C9A—C8A	125.0 (2)
C1B—C2B—Cl1B	119.2 (2)	O2A—C9A—C8A	112.00 (18)
C3B—C2B—Cl1B	119.3 (2)	O1B—C9B—O2B	122.9 (2)
C4A—C3A—C2A	118.4 (2)	O1B—C9B—C8B	125.4 (2)
C4A—C3A—H3A	120.8	O2B—C9B—C8B	111.7 (2)
C2A—C3A—H3A	120.8	O2A—C10A—H10A	109.5
C4B—C3B—C2B	118.5 (3)	O2A—C10A—H10B	109.5
C4B—C3B—H3B	120.7	H10A—C10A—H10B	109.5
C2B—C3B—H3B	120.7	O2A—C10A—H10C	109.5
C3A—C4A—C5A	121.1 (2)	H10A—C10A—H10C	109.5
C3A—C4A—H4A	119.5	H10B—C10A—H10C	109.5
C5A—C4A—H4A	119.5	O2B—C10B—H10D	109.5
C3B—C4B—C5B	121.0 (2)	O2B—C10B—H10E	109.5
C3B—C4B—H4B	119.5	H10D—C10B—H10E	109.5
C5B—C4B—H4B	119.5	O2B—C10B—H10F	109.5
C4A—C5A—C6A	120.3 (2)	H10D—C10B—H10F	109.5
C4A—C5A—H5A	119.8	H10E—C10B—H10F	109.5
C6A—C5A—H5A	119.8	C8A—C11A—Br1A	111.48 (15)
C4B—C5B—C6B	120.2 (3)	C8A—C11A—H11A	109.3
C4B—C5B—H5B	119.9	Br1A—C11A—H11A	109.3
C6B—C5B—H5B	119.9	C8A—C11A—H11B	109.3
C1A—C6A—C5A	118.0 (2)	Br1A—C11A—H11B	109.3
C1A—C6A—C7A	116.98 (19)	H11A—C11A—H11B	108.0
C5A—C6A—C7A	125.0 (2)	C8B—C11B—Br1B	113.16 (16)
C1B—C6B—C5B	118.5 (2)	C8B—C11B—H11C	108.9
C1B—C6B—C7B	117.6 (2)	Br1B—C11B—H11C	108.9
C5B—C6B—C7B	123.7 (2)	C8B—C11B—H11D	108.9
C8A—C7A—C6A	131.42 (19)	Br1B—C11B—H11D	108.9
C8A—C7A—H7A	114.3	H11C—C11B—H11D	107.8
C6A—C7A—H7A	114.3	C9A—O2A—C10A	115.59 (19)
C8B—C7B—C6B	129.8 (2)	C9B—O2B—C10B	114.8 (2)
C6A—C1A—C2A—C3A	−1.3 (4)	C1B—C6B—C7B—C8B	−153.1 (2)
C6A—C1A—C2A—Cl1A	178.57 (18)	C5B—C6B—C7B—C8B	31.3 (4)
C6B—C1B—C2B—C3B	1.7 (4)	C6A—C7A—C8A—C11A	−3.2 (4)
C6B—C1B—C2B—Cl1B	179.77 (19)	C6A—C7A—C8A—C9A	−179.4 (2)
C1A—C2A—C3A—C4A	−0.5 (4)	C6B—C7B—C8B—C11B	6.4 (4)
Cl1A—C2A—C3A—C4A	179.6 (2)	C6B—C7B—C8B—C9B	−178.6 (2)
C1B—C2B—C3B—C4B	−0.6 (4)	C7A—C8A—C9A—O1A	11.0 (3)
Cl1B—C2B—C3B—C4B	−178.7 (2)	C11A—C8A—C9A—O1A	−165.5 (2)
C2A—C3A—C4A—C5A	1.6 (4)	C7A—C8A—C9A—O2A	−170.21 (19)
C2B—C3B—C4B—C5B	−0.3 (4)	C11A—C8A—C9A—O2A	13.3 (3)
C3A—C4A—C5A—C6A	−0.8 (4)	C7B—C8B—C9B—O1B	−2.9 (3)
C3B—C4B—C5B—C6B	0.1 (5)	C11B—C8B—C9B—O1B	172.4 (2)
C2A—C1A—C6A—C5A	2.0 (3)	C7B—C8B—C9B—O2B	177.7 (2)
C2A—C1A—C6A—C7A	−178.6 (2)	C11B—C8B—C9B—O2B	−7.0 (3)
C4A—C5A—C6A—C1A	−1.0 (4)	C7A—C8A—C11A—Br1A	95.1 (2)
C4A—C5A—C6A—C7A	179.6 (2)	C9A—C8A—C11A—Br1A	−88.7 (2)
C2B—C1B—C6B—C5B	−1.9 (4)	C7B—C8B—C11B—Br1B	−101.0 (2)
C2B—C1B—C6B—C7B	−177.7 (2)	C9B—C8B—C11B—Br1B	84.2 (2)
C4B—C5B—C6B—C1B	1.0 (4)	O1A—C9A—O2A—C10A	−0.3 (3)
C4B—C5B—C6B—C7B	176.5 (2)	C8A—C9A—O2A—C10A	−179.1 (2)
C1A—C6A—C7A—C8A	157.6 (2)	O1B—C9B—O2B—C10B	0.7 (4)
C5A—C6A—C7A—C8A	−23.1 (4)	C8B—C9B—O2B—C10B	−179.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C1A—H1A···O1Bi	0.93	2.53	3.429 (3)	161
C1B—H1B···O1Ai	0.93	2.51	3.380 (3)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1A—H1A⋯O1B i	0.93	2.53	3.429 (3)	161
C1B—H1B⋯O1A i	0.93	2.51	3.380 (3)	156

Symmetry code: (i) .