(E)-1,2-Bis(3-bromo-4-methyl-phen-yl)ethene.

In the structure of the title compound, C(16)H(14)Br(2), the central C=C bond length is 1.329 (4) Å and the two benzene rings are approximately coplanar with the double bond, with twist angles of 7.5 (2) and 13.6 (2)°.

Related literature

For related literature, see: Daik et al. (1998 ▶); Harada & Ogawa et al. (2004 ▶); Ogawa et al. (1992 ▶); Mallory et al. (2001 ▶).

Experimental

Crystal data

C16H14Br2

M = 366.09

Monoclinic,

a = 6.3301 (4) Å

b = 7.6499 (5) Å

c = 28.164 (2) Å

β = 91.208 (1)°

V = 1363.55 (16) Å3

Z = 4

Mo Kα radiation

μ = 5.92 mm−1

T = 173 (2) K

0.27 × 0.19 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.303, T max = 0.578

14025 measured reflections

2793 independent reflections

2393 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.054

S = 1.08

2793 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: APEX2; data reduction: SAINT-Plus (Bruker, 2006 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990 ▶); program(s) used to refine structure: SHELXTL (Sheldrick, 2003 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807067645/pv2061sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807067645/pv2061Isup2.hkl

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

C16H14Br2	Z = 4
Mr = 366.09	F000 = 720
Monoclinic, P21/c	Dx = 1.783 Mg m−3
Hall symbol: -P2ybc	Melting point: 424.75 K
a = 6.3301 (4) Å	Mo Kα radiation λ = 0.71073 Å
b = 7.6499 (5) Å	µ = 5.92 mm−1
c = 28.164 (2) Å	T = 173 (2) K
β = 91.208 (1)º	Prism, colourless
V = 1363.55 (16) Å3	0.27 × 0.19 × 0.10 mm

Bruker APEXII CCD area-detector diffractometer	2793 independent reflections
Monochromator: graphite	2393 reflections with I > 2σ(I)
T = 173(2) K	Rint = 0.027
P = 101 kPa	θmax = 26.4º
φ and ω scans	θmin = 2.8º
Absorption correction: multi-scan(SADABS; Sheldrick, 2004)	h = −7→7
Tmin = 0.303, Tmax = 0.578	k = −9→9
14025 measured reflections	l = −35→35

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.025	H-atom parameters constrained
wR(F2) = 0.054	w = 1/[σ2(Fo2) + (0.0179P)2 + 1.6865P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.001
2793 reflections	Δρmax = 0.43 e Å−3
165 parameters	Δρmin = −0.32 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.08255 (4)	0.93057 (4)	0.562520 (9)	0.02689 (8)
C1	0.0145 (4)	0.8529 (3)	0.62456 (8)	0.0197 (5)
C2	−0.1806 (4)	0.7739 (3)	0.63183 (9)	0.0217 (5)
C3	−0.2158 (4)	0.7151 (3)	0.67779 (10)	0.0241 (6)
H3	−0.3476	0.6620	0.6844	0.029*
C4	−0.0673 (4)	0.7309 (3)	0.71400 (9)	0.0237 (6)
H4	−0.0972	0.6867	0.7446	0.028*
C5	0.1280 (4)	0.8119 (3)	0.70600 (9)	0.0213 (6)
C6	0.1650 (4)	0.8749 (3)	0.66049 (9)	0.0212 (5)
H6	0.2939	0.9332	0.6541	0.025*
C7	0.2912 (4)	0.8315 (4)	0.74343 (9)	0.0241 (6)
H7	0.4101	0.9015	0.7361	0.029*
C8	−0.3452 (4)	0.7506 (4)	0.59307 (10)	0.0282 (6)
H8A	−0.2872	0.6792	0.5676	0.034*
H8B	−0.3865	0.8653	0.5804	0.034*
H8C	−0.4693	0.6922	0.6060	0.034*
Br2	0.44176 (4)	0.73105 (4)	0.971236 (9)	0.02871 (8)
C11	0.5297 (4)	0.7870 (3)	0.90906 (9)	0.0205 (5)
C12	0.7254 (4)	0.8675 (3)	0.90274 (9)	0.0218 (5)
C13	0.7768 (4)	0.9044 (3)	0.85612 (10)	0.0243 (6)
H13	0.9102	0.9558	0.8501	0.029*
C14	0.6420 (4)	0.8695 (4)	0.81816 (9)	0.0253 (6)
H14	0.6834	0.8991	0.7869	0.030*
C15	0.4454 (4)	0.7913 (3)	0.82503 (9)	0.0218 (6)
C16	0.3931 (4)	0.7476 (3)	0.87155 (9)	0.0224 (6)
H16	0.2629	0.6906	0.8774	0.027*
C17	0.2894 (4)	0.7613 (4)	0.78658 (9)	0.0250 (6)
H17	0.1761	0.6842	0.7932	0.030*
C18	0.8708 (4)	0.9153 (4)	0.94351 (10)	0.0279 (6)
H18A	0.8014	1.0011	0.9638	0.033*
H18B	1.0011	0.9656	0.9313	0.033*
H18C	0.9047	0.8104	0.9621	0.033*

	U11	U22	U33	U12	U13	U23
Br1	0.02994 (15)	0.03138 (16)	0.01930 (14)	−0.00196 (12)	−0.00088 (10)	0.00574 (11)
C1	0.0243 (14)	0.0192 (13)	0.0157 (12)	0.0034 (11)	0.0018 (10)	0.0006 (10)
C2	0.0207 (13)	0.0217 (14)	0.0226 (13)	0.0025 (11)	−0.0021 (10)	−0.0016 (11)
C3	0.0214 (13)	0.0219 (14)	0.0291 (15)	0.0000 (11)	0.0031 (11)	0.0012 (11)
C4	0.0295 (15)	0.0221 (14)	0.0196 (13)	0.0031 (11)	0.0033 (11)	−0.0001 (11)
C5	0.0252 (14)	0.0196 (13)	0.0190 (13)	0.0025 (11)	0.0001 (11)	−0.0042 (10)
C6	0.0193 (13)	0.0224 (14)	0.0218 (13)	−0.0019 (11)	0.0014 (10)	−0.0017 (11)
C7	0.0253 (14)	0.0256 (15)	0.0213 (14)	0.0010 (11)	0.0001 (11)	−0.0028 (11)
C8	0.0247 (14)	0.0314 (16)	0.0283 (15)	−0.0022 (12)	−0.0052 (11)	−0.0001 (12)
Br2	0.03120 (16)	0.03709 (17)	0.01781 (14)	−0.00261 (12)	−0.00030 (11)	0.00279 (12)
C11	0.0259 (14)	0.0184 (13)	0.0172 (13)	0.0044 (11)	0.0003 (10)	0.0014 (10)
C12	0.0221 (13)	0.0169 (13)	0.0262 (14)	0.0042 (10)	−0.0029 (11)	−0.0014 (11)
C13	0.0192 (13)	0.0218 (14)	0.0321 (15)	0.0008 (11)	0.0027 (11)	0.0016 (11)
C14	0.0298 (15)	0.0249 (14)	0.0213 (14)	0.0026 (12)	0.0030 (11)	0.0018 (11)
C15	0.0251 (14)	0.0185 (13)	0.0217 (13)	0.0028 (11)	−0.0017 (11)	−0.0011 (10)
C16	0.0216 (13)	0.0216 (14)	0.0240 (14)	−0.0008 (11)	−0.0008 (10)	0.0009 (11)
C17	0.0287 (15)	0.0243 (14)	0.0218 (14)	−0.0022 (12)	−0.0013 (11)	−0.0023 (11)
C18	0.0272 (15)	0.0248 (15)	0.0314 (15)	−0.0020 (12)	−0.0052 (12)	−0.0019 (12)

Br1—C1	1.904 (2)	Br2—C11	1.898 (3)
C1—C6	1.386 (3)	C11—C16	1.385 (4)
C1—C2	1.393 (4)	C11—C12	1.398 (4)
C2—C3	1.393 (4)	C12—C13	1.389 (4)
C2—C8	1.504 (4)	C12—C18	1.502 (4)
C3—C4	1.378 (4)	C13—C14	1.380 (4)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.405 (4)	C14—C15	1.398 (4)
C4—H4	0.9500	C14—H14	0.9500
C5—C6	1.394 (4)	C15—C16	1.399 (4)
C5—C7	1.468 (4)	C15—C17	1.468 (4)
C6—H6	0.9500	C16—H16	0.9500
C7—C17	1.329 (4)	C17—H17	0.9500
C7—H7	0.9500	C18—H18A	0.9800
C8—H8A	0.9800	C18—H18B	0.9800
C8—H8B	0.9800	C18—H18C	0.9800
C8—H8C	0.9800
C6—C1—C2	122.9 (2)	C16—C11—C12	122.7 (2)
C6—C1—Br1	117.82 (19)	C16—C11—Br2	117.7 (2)
C2—C1—Br1	119.25 (19)	C12—C11—Br2	119.67 (19)
C3—C2—C1	115.9 (2)	C13—C12—C11	115.9 (2)
C3—C2—C8	120.9 (2)	C13—C12—C18	121.4 (2)
C1—C2—C8	123.2 (2)	C11—C12—C18	122.7 (2)
C4—C3—C2	122.6 (3)	C14—C13—C12	122.7 (3)
C4—C3—H3	118.7	C14—C13—H13	118.7
C2—C3—H3	118.7	C12—C13—H13	118.7
C3—C4—C5	120.6 (2)	C13—C14—C15	120.9 (2)
C3—C4—H4	119.7	C13—C14—H14	119.6
C5—C4—H4	119.7	C15—C14—H14	119.6
C6—C5—C4	117.7 (2)	C14—C15—C16	117.5 (2)
C6—C5—C7	119.7 (2)	C14—C15—C17	123.5 (2)
C4—C5—C7	122.6 (2)	C16—C15—C17	119.0 (2)
C1—C6—C5	120.2 (2)	C11—C16—C15	120.4 (2)
C1—C6—H6	119.9	C11—C16—H16	119.8
C5—C6—H6	119.9	C15—C16—H16	119.8
C17—C7—C5	126.6 (3)	C7—C17—C15	126.4 (3)
C17—C7—H7	116.7	C7—C17—H17	116.8
C5—C7—H7	116.7	C15—C17—H17	116.8
C2—C8—H8A	109.5	C12—C18—H18A	109.5
C2—C8—H8B	109.5	C12—C18—H18B	109.5
H8A—C8—H8B	109.5	H18A—C18—H18B	109.5
C2—C8—H8C	109.5	C12—C18—H18C	109.5
H8A—C8—H8C	109.5	H18A—C18—H18C	109.5
H8B—C8—H8C	109.5	H18B—C18—H18C	109.5
Br2—C11—C12—C18	−1.0 (3)	C6—C5—C7—C17	−171.7 (3)
Br1—C1—C2—C8	−1.7 (4)	C16—C15—C17—C7	162.7 (3)
C4—C5—C7—C17	8.2 (4)	C5—C7—C17—C15	−175.4 (2)
C14—C15—C17—C7	−14.1 (4)