(E)-Ethyl 3-(3-bromo-phen-yl)-2-cyano-acrylate.

The title mol-ecule, C(12)H(10)BrNO(2), adopts an E configuration with respect to the C=C bond of the acrylate unit. In the crystal structure, mol-ecules are connected by a pair of inter-molecular C-H⋯O hydrogen bonds, forming a centrosymmetric dimer.

Related literature

For the synthesis, see: Lapworth & Baker (1927 ▶). For the title compound as an inter­mediate in drug synthesis, see: Obniska et al. (2005 ▶).

Experimental

Crystal data

C12H10BrNO2

M = 280.12

Monoclinic,

a = 7.6147 (7) Å

b = 21.6015 (19) Å

c = 7.6044 (7) Å

β = 110.370 (1)°

V = 1172.62 (18) Å3

Z = 4

Mo Kα radiation

μ = 3.49 mm−1

T = 298 K

0.17 × 0.14 × 0.09 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (; Sheldrick, 1996 ▶) T min = 0.597, T max = 0.751

10143 measured reflections

2698 independent reflections

1730 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.081

S = 1.00

2698 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.33 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809039518/is2461sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039518/is2461Isup2.hkl

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

C12H10BrNO2	F(000) = 560
Mr = 280.12	Dx = 1.587 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2803 reflections
a = 7.6147 (7) Å	θ = 2.9–25.8°
b = 21.6015 (19) Å	µ = 3.49 mm−1
c = 7.6044 (7) Å	T = 298 K
β = 110.370 (1)°	Block, colorless
V = 1172.62 (18) Å3	0.17 × 0.14 × 0.09 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	2698 independent reflections
Radiation source: fine-focus sealed tube	1730 reflections with I > 2σ(I)
graphite	Rint = 0.038
φ and ω scans	θmax = 27.6°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.597, Tmax = 0.751	k = −28→28
10143 measured reflections	l = −8→9

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) = 0.081	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0337P)2 + 0.2149P] where P = (Fo2 + 2Fc2)/3
2698 reflections	(Δ/σ)max = 0.001
146 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.33 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
Br1	1.32627 (4)	0.459872 (14)	0.80815 (5)	0.06743 (14)
C5	1.1401 (4)	0.40161 (12)	0.6781 (4)	0.0491 (7)
C6	0.9564 (4)	0.42010 (12)	0.6053 (4)	0.0464 (6)
H6	0.9240	0.4608	0.6193	0.056*
C7	0.6257 (4)	0.39971 (12)	0.4366 (4)	0.0481 (6)
H7	0.6060	0.4373	0.4862	0.058*
C1	0.8179 (3)	0.37725 (11)	0.5098 (4)	0.0460 (6)
N1	0.4728 (3)	0.27353 (12)	0.1299 (4)	0.0694 (7)
C8	0.4721 (3)	0.37490 (11)	0.3089 (3)	0.0438 (6)
C4	1.1939 (4)	0.34169 (14)	0.6612 (4)	0.0626 (8)
H4	1.3192	0.3301	0.7101	0.075*
C2	0.8709 (4)	0.31640 (13)	0.4958 (4)	0.0629 (8)
H2	0.7806	0.2870	0.4362	0.075*
C10	−0.0327 (4)	0.40634 (13)	0.0878 (4)	0.0579 (8)
H10A	−0.0360	0.4404	0.0035	0.069*
H10B	−0.0578	0.4225	0.1957	0.069*
C11	−0.1756 (4)	0.35851 (14)	−0.0101 (5)	0.0682 (9)
H11A	−0.1452	0.3412	−0.1122	0.102*
H11B	−0.2972	0.3774	−0.0577	0.102*
H11C	−0.1759	0.3263	0.0768	0.102*
C3	1.0573 (4)	0.29951 (14)	0.5701 (5)	0.0754 (10)
H3	1.0912	0.2588	0.5582	0.090*
O2	0.1493 (2)	0.37612 (8)	0.1469 (2)	0.0517 (5)
O1	0.2787 (3)	0.46073 (9)	0.3104 (3)	0.0703 (6)
C12	0.4724 (3)	0.31789 (13)	0.2110 (4)	0.0500 (7)
C9	0.2926 (4)	0.40931 (13)	0.2581 (4)	0.0493 (7)

	U11	U22	U33	U12	U13	U23
Br1	0.04546 (19)	0.0595 (2)	0.0794 (2)	−0.00844 (14)	−0.00088 (15)	−0.00303 (16)
C5	0.0422 (15)	0.0497 (16)	0.0478 (16)	−0.0039 (12)	0.0061 (13)	0.0000 (12)
C6	0.0477 (16)	0.0381 (14)	0.0488 (16)	0.0000 (11)	0.0109 (12)	0.0000 (12)
C7	0.0445 (15)	0.0409 (14)	0.0548 (17)	−0.0001 (11)	0.0119 (13)	−0.0013 (12)
C1	0.0394 (14)	0.0436 (14)	0.0476 (16)	−0.0031 (11)	0.0058 (12)	0.0004 (12)
N1	0.0519 (15)	0.0609 (16)	0.092 (2)	−0.0110 (12)	0.0204 (14)	−0.0237 (15)
C8	0.0381 (14)	0.0438 (14)	0.0474 (16)	−0.0023 (11)	0.0123 (12)	−0.0003 (12)
C4	0.0421 (16)	0.0558 (17)	0.076 (2)	0.0073 (13)	0.0024 (15)	−0.0037 (15)
C2	0.0503 (17)	0.0469 (16)	0.074 (2)	−0.0019 (13)	−0.0010 (15)	−0.0078 (14)
C10	0.0349 (15)	0.0605 (18)	0.073 (2)	0.0057 (13)	0.0125 (14)	−0.0015 (15)
C11	0.0390 (16)	0.077 (2)	0.079 (2)	−0.0025 (15)	0.0092 (15)	0.0018 (17)
C3	0.0539 (19)	0.0490 (17)	0.102 (3)	0.0099 (14)	0.0000 (18)	−0.0102 (17)
O2	0.0350 (10)	0.0511 (11)	0.0634 (12)	−0.0005 (8)	0.0098 (9)	−0.0070 (9)
O1	0.0505 (12)	0.0600 (13)	0.0904 (16)	0.0028 (10)	0.0119 (11)	−0.0251 (11)
C12	0.0329 (14)	0.0529 (16)	0.0594 (18)	−0.0069 (12)	0.0098 (13)	−0.0009 (14)
C9	0.0410 (15)	0.0534 (17)	0.0505 (17)	−0.0041 (12)	0.0120 (13)	−0.0033 (13)

Br1—C5	1.896 (2)	C4—H4	0.9300
C5—C6	1.372 (3)	C2—C3	1.382 (4)
C5—C4	1.377 (4)	C2—H2	0.9300
C6—C1	1.401 (3)	C10—O2	1.454 (3)
C6—H6	0.9300	C10—C11	1.497 (4)
C7—C8	1.344 (3)	C10—H10A	0.9700
C7—C1	1.456 (3)	C10—H10B	0.9700
C7—H7	0.9300	C11—H11A	0.9600
C1—C2	1.390 (4)	C11—H11B	0.9600
N1—C12	1.140 (3)	C11—H11C	0.9600
C8—C12	1.439 (4)	C3—H3	0.9300
C8—C9	1.484 (4)	O2—C9	1.333 (3)
C4—C3	1.374 (4)	O1—C9	1.197 (3)
C6—C5—C4	122.0 (2)	O2—C10—C11	107.1 (2)
C6—C5—Br1	119.3 (2)	O2—C10—H10A	110.3
C4—C5—Br1	118.7 (2)	C11—C10—H10A	110.3
C5—C6—C1	119.6 (2)	O2—C10—H10B	110.3
C5—C6—H6	120.2	C11—C10—H10B	110.3
C1—C6—H6	120.2	H10A—C10—H10B	108.6
C8—C7—C1	130.5 (2)	C10—C11—H11A	109.5
C8—C7—H7	114.8	C10—C11—H11B	109.5
C1—C7—H7	114.8	H11A—C11—H11B	109.5
C2—C1—C6	118.6 (2)	C10—C11—H11C	109.5
C2—C1—C7	124.5 (2)	H11A—C11—H11C	109.5
C6—C1—C7	116.9 (2)	H11B—C11—H11C	109.5
C7—C8—C12	123.9 (2)	C4—C3—C2	121.3 (3)
C7—C8—C9	118.6 (2)	C4—C3—H3	119.3
C12—C8—C9	117.5 (2)	C2—C3—H3	119.3
C3—C4—C5	118.2 (3)	C9—O2—C10	115.9 (2)
C3—C4—H4	120.9	N1—C12—C8	178.3 (3)
C5—C4—H4	120.9	O1—C9—O2	124.2 (3)
C3—C2—C1	120.2 (3)	O1—C9—C8	124.0 (2)
C3—C2—H2	119.9	O2—C9—C8	111.8 (2)
C1—C2—H2	119.9
C4—C5—C6—C1	−0.3 (4)	C7—C1—C2—C3	−179.9 (3)
Br1—C5—C6—C1	−179.72 (19)	C5—C4—C3—C2	0.5 (5)
C5—C6—C1—C2	1.6 (4)	C1—C2—C3—C4	0.9 (5)
C5—C6—C1—C7	179.8 (2)	C11—C10—O2—C9	−171.7 (2)
C8—C7—C1—C2	−17.9 (5)	C10—O2—C9—O1	0.5 (4)
C8—C7—C1—C6	164.1 (3)	C10—O2—C9—C8	−179.3 (2)
C1—C7—C8—C12	−1.8 (5)	C7—C8—C9—O1	7.3 (4)
C1—C7—C8—C9	−178.8 (3)	C12—C8—C9—O1	−169.9 (3)
C6—C5—C4—C3	−0.8 (5)	C7—C8—C9—O2	−172.8 (2)
Br1—C5—C4—C3	178.7 (2)	C12—C8—C9—O2	9.9 (3)
C6—C1—C2—C3	−1.9 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1i	0.93	2.47	3.323 (3)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1i	0.93	2.47	3.323 (3)	152

Symmetry code: (i) .