Methyl (2Z)-2-bromo-methyl-3-(2,4-dichloro-phen-yl)prop-2-enoate.

In the title compound C11H9BrCl2O2, which represents the Z isomer, the methyl-acrylate moiety is essentially planar within 0.039 (2) Å and has an extended trans configuration. The benzene ring makes a dihedral angle of 28.3 (1)° with the mean plane of the methyl-acrylate moiety. The crystal packing is characterized by C-H⋯O hydrogen bonding and halogen-halogen inter-actions [Cl⋯Cl = 3.486 (3) Å], resulting in the formation of R 2 (2)(11) ring motifs and connecting the mol-ecules into chains propagating along the b axis.

Related literature

For the uses of cinnamic acid and its derivatives, see: Xiao et al. (2008 ▶); De Fraine & Martin (1991 ▶). For the extended conformation of acrylate, see: Schweizer & Dunitz (1982 ▶). For a related structure, see: Karthikeyan et al. (2012 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶). For type I halogen inter­actions, see: Johnson & Lemmerer (2012 ▶); Schmidt et al. (2011 ▶).

Experimental

Crystal data

C11H9BrCl2O2

M = 323.99

Triclinic,

a = 7.9174 (3) Å

b = 8.8032 (3) Å

c = 9.3585 (3) Å

α = 78.374 (2)°

β = 86.599 (2)°

γ = 73.528 (2)°

V = 612.67 (4) Å3

Z = 2

Mo Kα radiation

μ = 3.77 mm−1

T = 293 K

0.25 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.405, T max = 0.470

16418 measured reflections

3748 independent reflections

2262 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.102

S = 1.00

3748 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.59 e Å−3

Δρmin = −0.29 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, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); 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/S1600536813007368/ld2096sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813007368/ld2096Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813007368/ld2096Isup3.cml

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

C11H9BrCl2O2	Z = 2
Mr = 323.99	F(000) = 320
Triclinic, P1	Dx = 1.756 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9174 (3) Å	Cell parameters from 3748 reflections
b = 8.8032 (3) Å	θ = 2.2–30.6°
c = 9.3585 (3) Å	µ = 3.77 mm−1
α = 78.374 (2)°	T = 293 K
β = 86.599 (2)°	Block, yellow
γ = 73.528 (2)°	0.25 × 0.25 × 0.20 mm
V = 612.67 (4) Å3

Bruker Kappa APEXII CCD diffractometer	3748 independent reflections
Radiation source: fine-focus sealed tube	2262 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
ω and φ scans	θmax = 30.6°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −11→11
Tmin = 0.405, Tmax = 0.470	k = −12→12
16418 measured reflections	l = −13→13

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0538P)2 + 0.0238P] where P = (Fo2 + 2Fc2)/3
3748 reflections	(Δ/σ)max = 0.005
146 parameters	Δρmax = 0.59 e Å−3
0 restraints	Δρmin = −0.29 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
C1	0.2787 (3)	0.5411 (3)	−0.0226 (3)	0.0472 (6)
H1	0.2484	0.5224	0.0756	0.057*
C2	0.3057 (3)	0.4177 (3)	−0.0979 (3)	0.0485 (6)
H2	0.2935	0.3175	−0.0513	0.058*
C3	0.3509 (3)	0.4437 (3)	−0.2424 (3)	0.0456 (6)
C4	0.3696 (3)	0.5905 (3)	−0.3132 (3)	0.0449 (5)
H4	0.4001	0.6071	−0.4115	0.054*
C5	0.3424 (3)	0.7123 (3)	−0.2360 (2)	0.0409 (5)
C6	0.2948 (3)	0.6937 (3)	−0.0878 (2)	0.0402 (5)
C7	0.2786 (3)	0.8231 (3)	−0.0076 (2)	0.0424 (5)
H7	0.3505	0.8903	−0.0403	0.051*
C8	0.1750 (3)	0.8592 (3)	0.1064 (2)	0.0416 (5)
C9	0.1931 (3)	0.9985 (3)	0.1650 (3)	0.0457 (6)
C10	0.1030 (4)	1.1546 (4)	0.3480 (3)	0.0701 (9)
H10A	0.2227	1.1438	0.3718	0.105*
H10B	0.0324	1.1564	0.4349	0.105*
H10C	0.0585	1.2534	0.2792	0.105*
C11	0.0395 (3)	0.7785 (3)	0.1709 (3)	0.0468 (6)
H11A	0.0034	0.7295	0.0983	0.056*
H11B	−0.0630	0.8590	0.1971	0.056*
O1	0.2835 (3)	1.0836 (2)	0.1128 (2)	0.0692 (6)
O2	0.0964 (3)	1.0191 (2)	0.2845 (2)	0.0595 (5)
Cl1	0.38993 (11)	0.28780 (9)	−0.33786 (9)	0.0670 (2)
Cl2	0.36663 (10)	0.89643 (7)	−0.32891 (7)	0.05947 (19)
Br1	0.12451 (4)	0.61222 (3)	0.34428 (3)	0.06038 (13)

	U11	U22	U33	U12	U13	U23
C1	0.0551 (14)	0.0448 (14)	0.0415 (13)	−0.0184 (12)	0.0036 (11)	−0.0025 (11)
C2	0.0534 (14)	0.0381 (12)	0.0556 (15)	−0.0199 (11)	0.0025 (11)	−0.0029 (11)
C3	0.0462 (13)	0.0407 (13)	0.0532 (14)	−0.0157 (11)	0.0046 (11)	−0.0124 (11)
C4	0.0493 (13)	0.0464 (14)	0.0414 (12)	−0.0179 (11)	0.0048 (10)	−0.0085 (11)
C5	0.0454 (12)	0.0358 (12)	0.0416 (12)	−0.0158 (10)	0.0019 (10)	−0.0019 (10)
C6	0.0416 (12)	0.0376 (12)	0.0413 (12)	−0.0122 (10)	0.0002 (9)	−0.0059 (10)
C7	0.0494 (13)	0.0381 (12)	0.0404 (12)	−0.0159 (10)	−0.0009 (10)	−0.0036 (10)
C8	0.0465 (12)	0.0391 (12)	0.0363 (12)	−0.0106 (10)	−0.0047 (10)	−0.0009 (10)
C9	0.0576 (14)	0.0415 (13)	0.0359 (12)	−0.0124 (11)	−0.0025 (10)	−0.0038 (10)
C10	0.079 (2)	0.0678 (19)	0.072 (2)	−0.0185 (16)	0.0056 (16)	−0.0375 (17)
C11	0.0469 (13)	0.0488 (14)	0.0442 (13)	−0.0151 (11)	−0.0003 (10)	−0.0054 (11)
O1	0.1119 (17)	0.0591 (12)	0.0510 (11)	−0.0479 (12)	0.0175 (11)	−0.0140 (9)
O2	0.0707 (12)	0.0581 (12)	0.0577 (12)	−0.0226 (10)	0.0141 (9)	−0.0268 (10)
Cl1	0.0846 (5)	0.0527 (4)	0.0762 (5)	−0.0307 (4)	0.0176 (4)	−0.0297 (4)
Cl2	0.0858 (5)	0.0439 (3)	0.0512 (4)	−0.0290 (3)	0.0154 (3)	−0.0039 (3)
Br1	0.0792 (2)	0.0610 (2)	0.04088 (16)	−0.02708 (15)	0.00521 (12)	−0.00037 (12)

C1—C2	1.371 (4)	C7—H7	0.9300
C1—C6	1.397 (3)	C8—C11	1.484 (3)
C1—H1	0.9300	C8—C9	1.485 (3)
C2—C3	1.369 (4)	C9—O1	1.195 (3)
C2—H2	0.9300	C9—O2	1.331 (3)
C3—C4	1.372 (3)	C10—O2	1.451 (3)
C3—Cl1	1.731 (3)	C10—H10A	0.9600
C4—C5	1.372 (3)	C10—H10B	0.9600
C4—H4	0.9300	C10—H10C	0.9600
C5—C6	1.404 (3)	C11—Br1	1.961 (2)
C5—Cl2	1.735 (2)	C11—H11A	0.9700
C6—C7	1.459 (3)	C11—H11B	0.9700
C7—C8	1.340 (3)
C2—C1—C6	122.5 (2)	C6—C7—H7	115.3
C2—C1—H1	118.7	C7—C8—C11	125.5 (2)
C6—C1—H1	118.7	C7—C8—C9	115.8 (2)
C3—C2—C1	119.2 (2)	C11—C8—C9	118.6 (2)
C3—C2—H2	120.4	O1—C9—O2	122.9 (2)
C1—C2—H2	120.4	O1—C9—C8	124.8 (2)
C2—C3—C4	121.3 (2)	O2—C9—C8	112.3 (2)
C2—C3—Cl1	119.7 (2)	O2—C10—H10A	109.5
C4—C3—Cl1	118.97 (19)	O2—C10—H10B	109.5
C5—C4—C3	118.6 (2)	H10A—C10—H10B	109.5
C5—C4—H4	120.7	O2—C10—H10C	109.5
C3—C4—H4	120.7	H10A—C10—H10C	109.5
C4—C5—C6	122.9 (2)	H10B—C10—H10C	109.5
C4—C5—Cl2	117.39 (18)	C8—C11—Br1	112.60 (15)
C6—C5—Cl2	119.75 (18)	C8—C11—H11A	109.1
C1—C6—C5	115.5 (2)	Br1—C11—H11A	109.1
C1—C6—C7	123.4 (2)	C8—C11—H11B	109.1
C5—C6—C7	120.9 (2)	Br1—C11—H11B	109.1
C8—C7—C6	129.4 (2)	H11A—C11—H11B	107.8
C8—C7—H7	115.3	C9—O2—C10	116.2 (2)
C6—C1—C2—C3	0.2 (4)	C1—C6—C7—C8	−34.5 (4)
C1—C2—C3—C4	0.0 (4)	C5—C6—C7—C8	150.7 (2)
C1—C2—C3—Cl1	178.65 (19)	C6—C7—C8—C11	−5.0 (4)
C2—C3—C4—C5	0.1 (4)	C6—C7—C8—C9	178.8 (2)
Cl1—C3—C4—C5	−178.53 (18)	C7—C8—C9—O1	4.7 (4)
C3—C4—C5—C6	−0.5 (4)	C11—C8—C9—O1	−171.8 (2)
C3—C4—C5—Cl2	−179.85 (18)	C7—C8—C9—O2	−175.2 (2)
C2—C1—C6—C5	−0.5 (4)	C11—C8—C9—O2	8.4 (3)
C2—C1—C6—C7	−175.6 (2)	C7—C8—C11—Br1	98.2 (2)
C4—C5—C6—C1	0.7 (3)	C9—C8—C11—Br1	−85.7 (2)
Cl2—C5—C6—C1	−179.97 (18)	O1—C9—O2—C10	1.3 (4)
C4—C5—C6—C7	175.9 (2)	C8—C9—O2—C10	−178.8 (2)
Cl2—C5—C6—C7	−4.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1i	0.93	2.33	3.238 (3)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.93	2.33	3.238 (3)	167

Symmetry code: (i) .