1-(3-Bromo-2-thien-yl)ethanone.

In the title compound, C(6)H(5)BrOS, the non-H and aromatic H atoms lie on a crystallographic mirror plane. In the crystal, mol-ecules are linked into chains propagating along the c axis by inter-molecular C-H⋯O hydrogen bonds.

Related literature

For the uses of acetyl thio­phenes, see: Ashalatha et al. (2009 ▶); Bando et al. (2010 ▶); Ito & Furukawa (1990 ▶); Lutz et al. (2005 ▶); Nakayama et al. (1989 ▶); Pelly et al. (2005 ▶); Yasuhara et al. (2002 ▶).

Experimental

Crystal data

C6H5BrOS

M = 205.07

Orthorhombic,

a = 6.8263 (17) Å

b = 13.149 (4) Å

c = 16.007 (4) Å

V = 1436.8 (7) Å3

Z = 8

Mo Kα radiation

μ = 5.92 mm−1

T = 293 K

0.25 × 0.21 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.313, T max = 0.384

12363 measured reflections

973 independent reflections

790 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.067

S = 1.06

973 reflections

56 parameters

H-atom parameters constrained

Δρmax = 0.68 e Å−3

Δρmin = −0.48 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 ▶) and ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810034677/ci5166sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810034677/ci5166Isup2.hkl

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

C6H5BrOS	F(000) = 800
Mr = 205.07	Dx = 1.896 Mg m−3
Orthorhombic, Cmca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2bc 2	Cell parameters from 1982 reflections
a = 6.8263 (17) Å	θ = 2.5–28.4°
b = 13.149 (4) Å	µ = 5.92 mm−1
c = 16.007 (4) Å	T = 293 K
V = 1436.8 (7) Å3	Block, yellow
Z = 8	0.25 × 0.21 × 0.20 mm

Bruker APEXII CCD area-detector diffractometer	973 independent reflections
Radiation source: fine-focus sealed tube	790 reflections with I > 2σ(I)
graphite	Rint = 0.041
ω and φ scans	θmax = 28.4°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −9→9
Tmin = 0.313, Tmax = 0.384	k = −17→17
12363 measured reflections	l = −21→20

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.067	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0333P)2 + 1.3829P] where P = (Fo2 + 2Fc2)/3
973 reflections	(Δ/σ)max = 0.001
56 parameters	Δρmax = 0.68 e Å−3
0 restraints	Δρmin = −0.48 e Å−3

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	Occ. (<1)
Br1	0.00000	0.01659 (3)	0.38478 (2)	0.0547 (1)
S5	0.00000	0.33480 (6)	0.30339 (5)	0.0463 (3)
O8	0.00000	0.19098 (19)	0.51639 (13)	0.0584 (9)
C2	0.00000	0.1452 (2)	0.33378 (18)	0.0365 (9)
C3	0.00000	0.1547 (3)	0.2458 (2)	0.0448 (10)
C4	0.00000	0.2530 (3)	0.2207 (2)	0.0479 (10)
C6	0.00000	0.2366 (2)	0.37465 (17)	0.0357 (9)
C7	0.00000	0.2587 (2)	0.46527 (19)	0.0389 (9)
C9	0.00000	0.3685 (3)	0.4922 (2)	0.0541 (11)
H3	0.00000	0.09970	0.20930	0.0540*
H4	0.00000	0.27350	0.16510	0.0570*
H9A	0.13140	0.39450	0.49060	0.0810*	0.500
H9B	−0.05010	0.37360	0.54810	0.0810*	0.500
H9C	−0.08130	0.40740	0.45510	0.0810*	0.500

	U11	U22	U33	U12	U13	U23
Br1	0.0910 (3)	0.0316 (2)	0.0415 (2)	0.0000	0.0000	−0.0009 (1)
S5	0.0590 (5)	0.0401 (4)	0.0397 (4)	0.0000	0.0000	0.0117 (3)
O8	0.106 (2)	0.0408 (13)	0.0285 (12)	0.0000	0.0000	0.0023 (10)
C2	0.0400 (16)	0.0399 (16)	0.0297 (14)	0.0000	0.0000	0.0021 (12)
C3	0.0512 (18)	0.0519 (18)	0.0314 (15)	0.0000	0.0000	−0.0035 (13)
C4	0.0526 (19)	0.063 (2)	0.0281 (14)	0.0000	0.0000	0.0069 (14)
C6	0.0428 (16)	0.0333 (14)	0.0309 (15)	0.0000	0.0000	0.0057 (11)
C7	0.0482 (17)	0.0354 (15)	0.0332 (15)	0.0000	0.0000	−0.0021 (12)
C9	0.079 (2)	0.0385 (16)	0.0448 (19)	0.0000	0.0000	−0.0061 (14)

Br1—C2	1.878 (3)	C3—H3	0.93
S5—C4	1.706 (4)	C4—H4	0.93
S5—C6	1.723 (3)	C9—H9A	0.96
O8—C7	1.209 (4)	C9—H9B	0.96
C2—C3	1.414 (4)	C9—H9C	0.96
C2—C6	1.368 (4)	C9—H9Ai	0.96
C3—C4	1.354 (6)	C9—H9Bi	0.96
C6—C7	1.479 (4)	C9—H9Ci	0.96
C7—C9	1.507 (5)
Br1···O8	3.114 (3)	C3···C3xi	3.4158 (11)
Br1···Br1ii	3.7144 (12)	C3···C3ix	3.4158 (11)
Br1···O8ii	3.155 (3)	C3···C3vi	3.4158 (11)
Br1···S5iii	3.8453 (15)	C4···O8xvi	3.352 (4)
Br1···Br1iv	3.7144 (12)	C4···O8xvii	3.352 (4)
Br1···O8iv	3.155 (3)	C4···S5x	3.5993 (17)
Br1···S5v	3.8453 (15)	C4···S5xi	3.5993 (17)
S5···C4vi	3.5993 (17)	C4···C4x	3.5397 (16)
S5···Br1vii	3.8453 (15)	C4···C4xi	3.5397 (16)
S5···Br1viii	3.8453 (15)	C4···S5ix	3.5993 (17)
S5···C4ix	3.5993 (17)	C4···S5vi	3.5993 (17)
S5···C4x	3.5993 (17)	C4···C4ix	3.5397 (16)
S5···C4xi	3.5993 (17)	C4···C4vi	3.5397 (16)
S5···H9Ci	2.6700	C7···C7xiv	3.5970 (17)
S5···H9C	2.6700	C7···C7xviii	3.5970 (17)
O8···Br1	3.114 (3)	C7···C7xix	3.5970 (17)
O8···C4xii	3.352 (4)	C7···C7xv	3.5970 (17)
O8···C4xiii	3.352 (4)	C9···C9xx	3.467 (6)
O8···Br1ii	3.155 (3)	C9···C9xxi	3.467 (6)
O8···Br1iv	3.155 (3)	H4···O8xvi	2.4300
O8···H4xii	2.4300	H4···O8xvii	2.4300
O8···H4xiii	2.4300	H9A···O8xviii	2.7600
O8···H9Axiv	2.7600	H9A···O8xv	2.7600
O8···H9Axv	2.7600	H9C···S5	2.6700
C3···C3x	3.4158 (11)
C4—S5—C6	92.36 (16)	C7—C9—H9B	109.00
Br1—C2—C3	120.8 (2)	C7—C9—H9C	109.00
Br1—C2—C6	125.7 (2)	C7—C9—H9Ai	109.00
C3—C2—C6	113.5 (3)	C7—C9—H9Bi	109.00
C2—C3—C4	112.3 (3)	C7—C9—H9Ci	109.00
S5—C4—C3	111.8 (2)	H9A—C9—H9B	109.00
S5—C6—C2	110.0 (2)	H9A—C9—H9C	109.00
S5—C6—C7	120.1 (2)	H9A—C9—H9Ai	138.00
C2—C6—C7	129.9 (2)	H9A—C9—H9Bi	71.00
O8—C7—C6	121.3 (3)	H9B—C9—H9C	109.00
O8—C7—C9	120.8 (3)	H9Ai—C9—H9B	71.00
C6—C7—C9	118.0 (2)	H9B—C9—H9Ci	138.00
C2—C3—H3	124.00	H9Bi—C9—H9C	138.00
C4—C3—H3	124.00	H9C—C9—H9Ci	71.00
S5—C4—H4	124.00	H9Ai—C9—H9Bi	109.00
C3—C4—H4	124.00	H9Ai—C9—H9Ci	109.00
C7—C9—H9A	109.00	H9Bi—C9—H9Ci	109.00
C6—S5—C4—C3	0.00	C3—C2—C6—S5	0.00
C4—S5—C6—C2	0.00	C3—C2—C6—C7	180.00
C4—S5—C6—C7	−180.00	C2—C3—C4—S5	0.00
Br1—C2—C3—C4	−180.00	S5—C6—C7—O8	−180.00
C6—C2—C3—C4	0.00	S5—C6—C7—C9	0.00
Br1—C2—C6—S5	180.00	C2—C6—C7—O8	0.00
Br1—C2—C6—C7	0.00	C2—C6—C7—C9	−180.00

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O8xvi	0.93	2.43	3.352 (4)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O8i	0.93	2.43	3.352 (4)	174

Symmetry code: (i) .