(E)-2-Bromo-methyl-3-(o-tol-yl)acrylo-nitrile.

The title compound C11H10BrN, has an E conformation at the C=C bond of the acrylo-nitrile unit. The vinyl group makes a dihedral angle of 44.53 (12)° with the benzene ring. In the crystal, weak C-H⋯π inter-actions involving the benzene ring are observed.

Related literature

For the biological activity of cyano­acrylates, see: Zhang et al. (2009 ▶); Obniska et al. (2005 ▶); For related structures, see: Ye et al. (2009 ▶); Suresh et al. (2012 ▶).

Experimental

Crystal data

C11H10BrN

M = 236.11

Monoclinic,

a = 7.5473 (8) Å

b = 11.7362 (10) Å

c = 11.5228 (11) Å

β = 96.436 (3)°

V = 1014.22 (17) Å3

Z = 4

Mo Kα radiation

μ = 4.00 mm−1

T = 295 K

0.20 × 0.20 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.435, T max = 0.535

8718 measured reflections

1960 independent reflections

1261 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.085

S = 1.00

1960 reflections

119 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.26 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: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813021041/gk2587sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813021041/gk2587Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813021041/gk2587Isup3.cml

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

C11H10BrN	F(000) = 472
Mr = 236.11	Dx = 1.546 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1980 reflections
a = 7.5473 (8) Å	θ = 2.5–25.8°
b = 11.7362 (10) Å	µ = 4.00 mm−1
c = 11.5228 (11) Å	T = 295 K
β = 96.436 (3)°	Block, colourless
V = 1014.22 (17) Å3	0.20 × 0.20 × 0.15 mm
Z = 4

Bruker APEXII CCD diffractometer	1960 independent reflections
Radiation source: fine-focus sealed tube	1261 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
Detector resolution: 0 pixels mm-1	θmax = 25.9°, θmin = 2.5°
ω and φ scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −14→13
Tmin = 0.435, Tmax = 0.535	l = −14→14
8718 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.036P)2 + 0.5483P] where P = (Fo2 + 2Fc2)/3
1960 reflections	(Δ/σ)max < 0.001
119 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

	x	y	z	Uiso*/Ueq
C1	0.7824 (4)	−0.0112 (3)	0.5604 (3)	0.0451 (8)
C2	0.8374 (5)	0.0182 (4)	0.6742 (3)	0.0587 (10)
H2	0.8886	−0.0372	0.7252	0.070*
C3	0.8186 (5)	0.1269 (4)	0.7146 (3)	0.0702 (12)
H3	0.8563	0.1443	0.7922	0.084*
C4	0.7448 (5)	0.2096 (4)	0.6414 (3)	0.0634 (11)
H4	0.7307	0.2831	0.6691	0.076*
C5	0.6911 (5)	0.1840 (3)	0.5260 (3)	0.0508 (9)
H5	0.6417	0.2406	0.4759	0.061*
C6	0.7101 (4)	0.0752 (3)	0.4843 (3)	0.0398 (8)
C7	0.6525 (4)	0.0464 (3)	0.3617 (3)	0.0411 (7)
H7	0.5936	−0.0227	0.3480	0.049*
C8	0.6760 (4)	0.1091 (3)	0.2682 (2)	0.0410 (8)
C9	0.7740 (5)	0.2128 (3)	0.2782 (3)	0.0496 (9)
C10	0.6063 (5)	0.0732 (3)	0.1480 (3)	0.0530 (9)
H10A	0.5312	0.1331	0.1112	0.064*
H10B	0.5336	0.0055	0.1521	0.064*
C11	0.8037 (5)	−0.1309 (3)	0.5196 (3)	0.0582 (9)
H11A	0.8550	−0.1767	0.5838	0.087*
H11B	0.8807	−0.1316	0.4587	0.087*
H11C	0.6892	−0.1611	0.4903	0.087*
N1	0.8572 (5)	0.2944 (3)	0.2831 (3)	0.0750 (10)
Br1	0.79897 (5)	0.04122 (4)	0.05323 (3)	0.07015 (19)

	U11	U22	U33	U12	U13	U23
C1	0.0373 (19)	0.053 (2)	0.0457 (18)	−0.0111 (16)	0.0080 (14)	0.0050 (16)
C2	0.057 (2)	0.076 (3)	0.0429 (19)	−0.011 (2)	0.0049 (17)	0.0097 (18)
C3	0.071 (3)	0.101 (4)	0.039 (2)	−0.023 (3)	0.0111 (19)	−0.011 (2)
C4	0.069 (3)	0.069 (3)	0.057 (2)	−0.013 (2)	0.026 (2)	−0.022 (2)
C5	0.053 (2)	0.050 (2)	0.052 (2)	−0.0022 (17)	0.0165 (16)	−0.0044 (16)
C6	0.0321 (17)	0.049 (2)	0.0398 (16)	−0.0060 (14)	0.0106 (14)	−0.0021 (14)
C7	0.0353 (17)	0.043 (2)	0.0452 (17)	0.0012 (15)	0.0058 (14)	−0.0036 (15)
C8	0.0381 (18)	0.043 (2)	0.0412 (17)	0.0057 (16)	0.0041 (14)	0.0000 (15)
C9	0.062 (2)	0.048 (2)	0.0392 (18)	0.005 (2)	0.0082 (16)	0.0103 (16)
C10	0.051 (2)	0.062 (2)	0.0444 (18)	0.0072 (17)	−0.0035 (15)	−0.0007 (15)
C11	0.055 (2)	0.053 (2)	0.065 (2)	−0.0032 (18)	0.0013 (18)	0.0105 (18)
N1	0.099 (3)	0.059 (2)	0.068 (2)	−0.011 (2)	0.0173 (18)	0.0085 (17)
Br1	0.0798 (3)	0.0886 (4)	0.0435 (2)	0.0105 (2)	0.01345 (18)	−0.00341 (19)

C1—C2	1.374 (4)	C7—C8	1.334 (4)
C1—C6	1.409 (4)	C7—H7	0.9300
C1—C11	1.495 (5)	C8—C9	1.422 (5)
C2—C3	1.371 (6)	C8—C10	1.486 (4)
C2—H2	0.9300	C9—N1	1.143 (4)
C3—C4	1.364 (6)	C10—Br1	1.950 (3)
C3—H3	0.9300	C10—H10A	0.9700
C4—C5	1.379 (5)	C10—H10B	0.9700
C4—H4	0.9300	C11—H11A	0.9600
C5—C6	1.378 (4)	C11—H11B	0.9600
C5—H5	0.9300	C11—H11C	0.9600
C6—C7	1.470 (4)
C2—C1—C6	117.9 (3)	C8—C7—H7	116.6
C2—C1—C11	120.2 (3)	C6—C7—H7	116.6
C6—C1—C11	121.8 (3)	C7—C8—C9	121.4 (3)
C3—C2—C1	121.7 (4)	C7—C8—C10	122.1 (3)
C3—C2—H2	119.2	C9—C8—C10	116.4 (3)
C1—C2—H2	119.2	N1—C9—C8	177.2 (4)
C4—C3—C2	120.2 (3)	C8—C10—Br1	111.6 (2)
C4—C3—H3	119.9	C8—C10—H10A	109.3
C2—C3—H3	119.9	Br1—C10—H10A	109.3
C3—C4—C5	119.8 (4)	C8—C10—H10B	109.3
C3—C4—H4	120.1	Br1—C10—H10B	109.3
C5—C4—H4	120.1	H10A—C10—H10B	108.0
C6—C5—C4	120.5 (3)	C1—C11—H11A	109.5
C6—C5—H5	119.8	C1—C11—H11B	109.5
C4—C5—H5	119.8	H11A—C11—H11B	109.5
C5—C6—C1	119.9 (3)	C1—C11—H11C	109.5
C5—C6—C7	121.1 (3)	H11A—C11—H11C	109.5
C1—C6—C7	119.0 (3)	H11B—C11—H11C	109.5
C8—C7—C6	126.7 (3)
C6—C1—C2—C3	1.8 (5)	C2—C1—C6—C7	179.2 (3)
C11—C1—C2—C3	−179.6 (3)	C11—C1—C6—C7	0.6 (4)
C1—C2—C3—C4	−0.4 (5)	C5—C6—C7—C8	41.9 (5)
C2—C3—C4—C5	−0.9 (5)	C1—C6—C7—C8	−139.4 (3)
C3—C4—C5—C6	0.5 (5)	C6—C7—C8—C9	3.9 (5)
C4—C5—C6—C1	1.0 (5)	C6—C7—C8—C10	−177.8 (3)
C4—C5—C6—C7	179.6 (3)	C7—C8—C10—Br1	−114.5 (3)
C2—C1—C6—C5	−2.1 (4)	C9—C8—C10—Br1	63.9 (3)
C11—C1—C6—C5	179.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···Cg1i	0.93	2.97	3.654 (7)	131
C11—H11B···Cg1ii	0.96	2.86	3.699 (1)	146

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯Cg1i	0.93	2.97	3.654 (7)	131
C11—H11B⋯Cg1ii	0.96	2.86	3.699 (1)	146

Symmetry codes: (i) ; (ii) .