4-Bromo-4'-(dimethyl-amino)stilbene.

In the title compound, C(16)H(16)BrN, the benzene rings are inclined to each other with a dihedral angle between their mean planes of 50.5 (3)° and the C=C bond adopts a cis conformation.

Related literature

For background information on photonic materials, see: He et al. (2008 ▶). For related systems of stilbene, see: Moreno-Fuquen et al. (2008 ▶, 2009 ▶). For literature related to the synthesis, see: Maryanoff & Reitz (1989 ▶).

Experimental

Crystal data

C16H16BrN

M = 302.21

Monoclinic,

a = 14.804 (2) Å

b = 6.0962 (5) Å

c = 15.2106 (10) Å

β = 95.331 (9)°

V = 1366.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 2.99 mm−1

T = 123 K

0.38 × 0.25 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.457, T max = 0.749

8606 measured reflections

2986 independent reflections

1533 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.075

wR(F 2) = 0.213

S = 0.99

2986 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.94 e Å−3

Δρmin = −0.54 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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: PARST95 (Nardelli, 1995 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809020492/hg2518sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020492/hg2518Isup2.hkl

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

C16H16BrN	F(000) = 616
Mr = 302.21	Dx = 1.469 Mg m−3
Monoclinic, P21/c	Melting point: 354(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 14.804 (2) Å	Cell parameters from 2824 reflections
b = 6.0962 (5) Å	θ = 2.7–29.0°
c = 15.2106 (10) Å	µ = 2.99 mm−1
β = 95.331 (9)°	T = 123 K
V = 1366.8 (2) Å3	Slab, yellow
Z = 4	0.38 × 0.25 × 0.10 mm

Bruker APEXII CCD diffractometer	2986 independent reflections
Radiation source: fine-focus sealed tube	1533 reflections with I > 2σ(I)
graphite	Rint = 0.064
φ and ω scans	θmax = 27.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −18→18
Tmin = 0.457, Tmax = 0.749	k = −7→7
8606 measured reflections	l = −19→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)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.213	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.1119P)2] where P = (Fo2 + 2Fc2)/3
2986 reflections	(Δ/σ)max < 0.001
165 parameters	Δρmax = 0.94 e Å−3
0 restraints	Δρmin = −0.54 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	0.36239 (6)	−0.41740 (14)	0.35579 (5)	0.0487 (4)
N1	−0.0563 (6)	0.4693 (11)	0.6162 (5)	0.055 (2)
C1	0.3671 (6)	−0.2184 (13)	0.4545 (5)	0.043 (2)
C2	0.4151 (6)	−0.2818 (16)	0.5312 (5)	0.055 (2)
H2	0.4433	−0.4217	0.5367	0.066*
C3	0.4210 (6)	−0.1319 (16)	0.6019 (5)	0.055 (2)
H3	0.4562	−0.1695	0.6552	0.066*
C4	0.3768 (5)	0.0699 (13)	0.5960 (5)	0.0394 (19)
C5	0.3297 (6)	0.1216 (13)	0.5151 (5)	0.046 (2)
H5	0.3014	0.2613	0.5089	0.055*
C6	0.3215 (6)	−0.0195 (14)	0.4429 (5)	0.050 (2)
H6	0.2871	0.0176	0.3892	0.061*
C7	0.3859 (6)	0.2246 (15)	0.6700 (5)	0.050 (2)
H7	0.4442	0.2300	0.7017	0.060*
C8	0.3242 (6)	0.3591 (14)	0.6993 (5)	0.047 (2)
H8	0.3483	0.4566	0.7442	0.056*
C9	0.2261 (6)	0.3859 (12)	0.6758 (4)	0.042 (2)
C10	0.1699 (6)	0.2157 (13)	0.6391 (4)	0.039 (2)
H10	0.1963	0.0776	0.6278	0.047*
C11	0.0804 (6)	0.2435 (12)	0.6198 (5)	0.041 (2)
H11	0.0458	0.1253	0.5936	0.049*
C12	0.0344 (6)	0.4455 (11)	0.6371 (5)	0.0369 (18)
C13	0.0914 (6)	0.6088 (12)	0.6775 (4)	0.042 (2)
H13	0.0663	0.7459	0.6924	0.050*
C14	0.1825 (6)	0.5720 (12)	0.6956 (5)	0.043 (2)
H14	0.2178	0.6859	0.7242	0.052*
C15	−0.1121 (6)	0.3046 (14)	0.5665 (6)	0.054 (2)
H15A	−0.0868	0.2745	0.5105	0.081*
H15B	−0.1742	0.3600	0.5547	0.081*
H15C	−0.1127	0.1692	0.6012	0.081*
C16	−0.1007 (6)	0.6780 (14)	0.6312 (6)	0.055 (2)
H16A	−0.0761	0.7393	0.6880	0.082*
H16B	−0.1661	0.6543	0.6319	0.082*
H16C	−0.0898	0.7805	0.5837	0.082*

	U11	U22	U33	U12	U13	U23
Br1	0.0677 (7)	0.0433 (5)	0.0349 (4)	0.0116 (4)	0.0043 (3)	−0.0004 (4)
N1	0.080 (7)	0.033 (4)	0.053 (4)	0.003 (4)	0.010 (4)	−0.008 (3)
C1	0.068 (6)	0.037 (5)	0.025 (4)	0.000 (4)	0.010 (4)	0.008 (3)
C2	0.057 (6)	0.069 (6)	0.038 (5)	0.022 (5)	0.001 (4)	0.001 (5)
C3	0.047 (6)	0.085 (7)	0.032 (4)	0.014 (5)	−0.001 (4)	0.005 (5)
C4	0.037 (5)	0.051 (5)	0.030 (4)	−0.010 (4)	0.002 (3)	−0.001 (4)
C5	0.061 (6)	0.043 (5)	0.036 (4)	0.003 (4)	0.014 (4)	0.006 (4)
C6	0.064 (6)	0.062 (6)	0.025 (4)	0.019 (5)	0.004 (4)	0.015 (4)
C7	0.058 (6)	0.059 (6)	0.031 (4)	−0.012 (5)	0.000 (4)	0.008 (4)
C8	0.066 (7)	0.052 (5)	0.024 (4)	−0.011 (5)	0.011 (4)	0.001 (4)
C9	0.075 (7)	0.030 (5)	0.020 (3)	−0.006 (4)	0.007 (3)	0.004 (3)
C10	0.065 (6)	0.036 (5)	0.019 (3)	−0.008 (4)	0.014 (3)	−0.007 (3)
C11	0.068 (7)	0.031 (4)	0.026 (4)	−0.017 (4)	0.012 (4)	0.001 (3)
C12	0.055 (6)	0.026 (4)	0.031 (4)	0.004 (4)	0.014 (3)	0.003 (3)
C13	0.082 (7)	0.021 (4)	0.024 (4)	−0.003 (4)	0.007 (4)	−0.004 (3)
C14	0.075 (7)	0.030 (4)	0.024 (4)	−0.011 (4)	0.005 (4)	−0.004 (3)
C15	0.068 (7)	0.038 (5)	0.055 (5)	−0.003 (4)	0.007 (4)	0.000 (4)
C16	0.069 (7)	0.045 (5)	0.049 (5)	0.006 (4)	0.001 (4)	−0.009 (4)

Br1—C1	1.927 (8)	C8—H8	0.9500
N1—C12	1.359 (11)	C9—C14	1.353 (11)
N1—C16	1.460 (10)	C9—C10	1.412 (10)
N1—C15	1.465 (11)	C10—C11	1.342 (11)
C1—C2	1.364 (10)	C10—H10	0.9500
C1—C6	1.391 (11)	C11—C12	1.443 (10)
C2—C3	1.408 (12)	C11—H11	0.9500
C2—H2	0.9500	C12—C13	1.408 (11)
C3—C4	1.392 (11)	C13—C14	1.371 (11)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.393 (10)	C14—H14	0.9500
C4—C7	1.465 (11)	C15—H15A	0.9800
C5—C6	1.392 (11)	C15—H15B	0.9800
C5—H5	0.9500	C15—H15C	0.9800
C6—H6	0.9500	C16—H16A	0.9800
C7—C8	1.334 (12)	C16—H16B	0.9800
C7—H7	0.9500	C16—H16C	0.9800
C8—C9	1.472 (12)
C12—N1—C16	120.5 (7)	C10—C9—C8	123.1 (7)
C12—N1—C15	123.1 (7)	C11—C10—C9	121.9 (8)
C16—N1—C15	115.9 (7)	C11—C10—H10	119.1
C2—C1—C6	124.3 (8)	C9—C10—H10	119.1
C2—C1—Br1	117.8 (6)	C10—C11—C12	122.7 (7)
C6—C1—Br1	117.9 (6)	C10—C11—H11	118.7
C1—C2—C3	117.4 (8)	C12—C11—H11	118.7
C1—C2—H2	121.3	N1—C12—C13	124.4 (7)
C3—C2—H2	121.3	N1—C12—C11	121.4 (7)
C4—C3—C2	121.9 (7)	C13—C12—C11	114.2 (8)
C4—C3—H3	119.0	C14—C13—C12	120.7 (7)
C2—C3—H3	119.0	C14—C13—H13	119.7
C3—C4—C5	116.8 (7)	C12—C13—H13	119.7
C3—C4—C7	120.7 (7)	C9—C14—C13	125.0 (7)
C5—C4—C7	122.4 (8)	C9—C14—H14	117.5
C6—C5—C4	123.8 (8)	C13—C14—H14	117.5
C6—C5—H5	118.1	N1—C15—H15A	109.5
C4—C5—H5	118.1	N1—C15—H15B	109.5
C1—C6—C5	115.7 (7)	H15A—C15—H15B	109.5
C1—C6—H6	122.2	N1—C15—H15C	109.5
C5—C6—H6	122.2	H15A—C15—H15C	109.5
C8—C7—C4	129.5 (8)	H15B—C15—H15C	109.5
C8—C7—H7	115.2	N1—C16—H16A	109.5
C4—C7—H7	115.2	N1—C16—H16B	109.5
C7—C8—C9	132.6 (8)	H16A—C16—H16B	109.5
C7—C8—H8	113.7	N1—C16—H16C	109.5
C9—C8—H8	113.7	H16A—C16—H16C	109.5
C14—C9—C10	115.4 (8)	H16B—C16—H16C	109.5
C14—C9—C8	121.3 (7)
C6—C1—C2—C3	−2.3 (14)	C14—C9—C10—C11	4.5 (10)
Br1—C1—C2—C3	177.7 (6)	C8—C9—C10—C11	178.7 (7)
C1—C2—C3—C4	2.7 (13)	C9—C10—C11—C12	−1.8 (10)
C2—C3—C4—C5	−2.9 (12)	C16—N1—C12—C13	3.1 (11)
C2—C3—C4—C7	−178.7 (8)	C15—N1—C12—C13	173.9 (7)
C3—C4—C5—C6	2.8 (12)	C16—N1—C12—C11	−177.6 (7)
C7—C4—C5—C6	178.5 (8)	C15—N1—C12—C11	−6.8 (11)
C2—C1—C6—C5	2.1 (13)	C10—C11—C12—N1	179.5 (7)
Br1—C1—C6—C5	−177.8 (6)	C10—C11—C12—C13	−1.1 (10)
C4—C5—C6—C1	−2.4 (12)	N1—C12—C13—C14	−179.3 (7)
C3—C4—C7—C8	−142.8 (9)	C11—C12—C13—C14	1.3 (9)
C5—C4—C7—C8	41.7 (13)	C10—C9—C14—C13	−4.4 (10)
C4—C7—C8—C9	7.1 (15)	C8—C9—C14—C13	−178.8 (7)
C7—C8—C9—C14	−160.7 (9)	C12—C13—C14—C9	1.5 (11)
C7—C8—C9—C10	25.4 (12)