(E)-3-(4-Bromo-5-methyl-thio-phen-2-yl)acrylo-nitrile.

In the title structure, C8H6BrNS, the molecules are planar with the exception of the methyl H atoms. In the crystal, molecules are linked by intermolecular C-H⋯N interactions to form ribbons parallel to the b axis. Groups of ribbons are arranged in a herringbone pattern to form a layered structure parallel to the ab plane.

Related literature

For related structures and their applications, see: Perner et al. (2003 ▶); Kose (2004 ▶); Chandra et al. (2006 ▶); Zhao et al. (2009 ▶); Pu et al. (2010 ▶); Dinçalp et al. (2011 ▶).

Experimental

Crystal data

C8H6BrNS

M = 228.11

Orthorhombic,

a = 6.1347 (5) Å

b = 7.1124 (3) Å

c = 19.8245 (13) Å

V = 864.99 (10) Å3

Z = 4

Mo Kα radiation

μ = 4.92 mm−1

T = 150 K

0.40 × 0.30 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: empirical (using intensity measurements) (DENZO/SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.243, T max = 0.639

3294 measured reflections

1910 independent reflections

1769 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.120

S = 1.05

1910 reflections

102 parameters

H-atom parameters constrained

Δρmax = 0.74 e Å−3

Δρmin = −1.12 e Å−3

Absolute structure: Flack (1983 ▶), 699 Friedel pairs

Absolute structure parameter: 0.03 (2)

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and SCALEPACK; 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 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and CHEMDRAW Ultra (Cambridge Soft, 2001 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813019752/hg5330sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813019752/hg5330Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813019752/hg5330Isup3.cml

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

C8H6BrNS	F(000) = 448
Mr = 228.11	Dx = 1.752 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1769 reflections
a = 6.1347 (5) Å	θ = 3.0–28.4°
b = 7.1124 (3) Å	µ = 4.92 mm−1
c = 19.8245 (13) Å	T = 150 K
V = 864.99 (10) Å3	Plate, yellow
Z = 4	0.40 × 0.30 × 0.10 mm

Nonius KappaCCD diffractometer	1910 independent reflections
Radiation source: fine-focus sealed tube	1769 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.060
CCD scans	θmax = 27.4°, θmin = 3.0°
Absorption correction: empirical (using intensity measurements) (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	h = −4→7
Tmin = 0.243, Tmax = 0.639	k = −9→7
3294 measured reflections	l = −25→20

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.048	w = 1/[σ2(Fo2) + (0.0412P)2 + 2.3854P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.120	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.74 e Å−3
1910 reflections	Δρmin = −1.12 e Å−3
102 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.030 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 699 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.03 (2)

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	−0.4336 (10)	−0.1420 (8)	0.7590 (3)	0.0265 (11)
C2	−0.2429 (10)	−0.1841 (9)	0.7200 (3)	0.0264 (12)
H2	−0.1959	−0.3079	0.7159	0.032*
C3	−0.1322 (9)	−0.0462 (8)	0.6895 (3)	0.0258 (12)
H3	−0.1824	0.0764	0.6946	0.031*
C4	0.0617 (10)	−0.0763 (7)	0.6489 (3)	0.0235 (11)
C5	0.1860 (10)	0.0569 (8)	0.6186 (3)	0.0222 (11)
H5	0.1553	0.1849	0.6203	0.027*
C6	0.3668 (10)	−0.0199 (8)	0.5843 (3)	0.0241 (12)
C7	0.3838 (8)	−0.2120 (7)	0.5887 (2)	0.0191 (11)
C8	0.5528 (11)	−0.3400 (7)	0.5583 (3)	0.0264 (12)
H8A	0.5059	−0.3791	0.5142	0.040*
H8B	0.5713	−0.4485	0.5865	0.040*
H8C	0.6888	−0.2741	0.5546	0.040*
N1	−0.5883 (9)	−0.1203 (8)	0.7912 (3)	0.0331 (11)
S1	0.1701 (3)	−0.2987 (2)	0.63524 (7)	0.0246 (3)
Br1	0.57000 (10)	0.12692 (8)	0.53635 (3)	0.0319 (2)

	U11	U22	U33	U12	U13	U23
C1	0.022 (3)	0.028 (3)	0.030 (3)	−0.001 (3)	0.000 (2)	0.000 (2)
C2	0.024 (3)	0.027 (3)	0.029 (3)	0.003 (2)	0.001 (2)	−0.005 (2)
C3	0.023 (3)	0.025 (3)	0.029 (3)	0.006 (2)	−0.002 (2)	−0.003 (2)
C4	0.016 (2)	0.025 (3)	0.030 (3)	0.003 (2)	−0.002 (2)	−0.001 (2)
C5	0.023 (3)	0.018 (2)	0.026 (3)	0.004 (2)	−0.006 (2)	−0.006 (2)
C6	0.025 (3)	0.024 (3)	0.023 (3)	−0.001 (2)	−0.001 (2)	−0.004 (2)
C7	0.021 (3)	0.019 (2)	0.017 (2)	0.002 (2)	−0.0057 (19)	0.0017 (19)
C8	0.032 (3)	0.019 (3)	0.028 (3)	0.002 (2)	0.002 (2)	0.003 (2)
N1	0.031 (3)	0.031 (2)	0.038 (3)	−0.008 (3)	0.002 (2)	−0.004 (2)
S1	0.0240 (7)	0.0207 (6)	0.0291 (7)	0.0007 (6)	0.0021 (6)	−0.0004 (5)
Br1	0.0332 (3)	0.0259 (3)	0.0368 (3)	−0.0021 (3)	0.0065 (3)	0.0040 (2)

C1—N1	1.154 (8)	C5—H5	0.9300
C1—C2	1.434 (8)	C6—C7	1.373 (7)
C2—C3	1.338 (8)	C6—Br1	1.884 (6)
C2—H2	0.9300	C7—C8	1.506 (8)
C3—C4	1.452 (8)	C7—S1	1.717 (5)
C3—H3	0.9300	C8—H8A	0.9600
C4—C5	1.356 (8)	C8—H8B	0.9600
C4—S1	1.737 (5)	C8—H8C	0.9600
C5—C6	1.412 (8)
N1—C1—C2	175.6 (7)	C7—C6—C5	114.5 (5)
C3—C2—C1	120.3 (5)	C7—C6—Br1	122.3 (4)
C3—C2—H2	119.8	C5—C6—Br1	123.3 (4)
C1—C2—H2	119.8	C6—C7—C8	128.9 (5)
C2—C3—C4	123.9 (5)	C6—C7—S1	109.5 (4)
C2—C3—H3	118.0	C8—C7—S1	121.6 (4)
C4—C3—H3	118.0	C7—C8—H8A	109.5
C5—C4—C3	127.1 (5)	C7—C8—H8B	109.5
C5—C4—S1	110.6 (4)	H8A—C8—H8B	109.5
C3—C4—S1	122.3 (4)	C7—C8—H8C	109.5
C4—C5—C6	112.6 (5)	H8A—C8—H8C	109.5
C4—C5—H5	123.7	H8B—C8—H8C	109.5
C6—C5—H5	123.7	C7—S1—C4	92.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N1i	0.93	2.59	3.501 (8)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯N1i	0.93	2.59	3.501 (8)	166

Symmetry code: (i) .