1-(2,5-Dichloro-3-thien-yl)ethanone: infinite sheets mediated by O⋯Cl halogen bonds.

In the title compound, C(6)H(4)Cl(2)OS, the acetyl group is almost coplanar with the thio-phene ring [dihedral angle = 4.01 (2)°]. In the crystal, short inter-molecular O⋯Cl contacts [2.9494 (14) and 3.1191 (14) Å] link the mol-ecules into infinite (100) sheets and aromatic π-π stacking [centroid-centroid separation = 3.5422 (10) Å] consolidates the packing.

Related literature

For a related structure and background references, see: Jasinski et al. (2010 ▶). For a related structure, see: Wen & Rasmussen (2007 ▶). For reference structural data, see: Allen et al. (1987 ▶). For a discussion of halogen bonding, see: Metrangalo & Resnati (2001 ▶).

Experimental

Crystal data

C6H4Cl2OS

M = 195.05

Orthorhombic,

a = 13.0980 (3) Å

b = 7.1790 (1) Å

c = 16.3290 (3) Å

V = 1535.42 (5) Å3

Z = 8

Mo Kα radiation

μ = 1.04 mm−1

T = 120 K

0.22 × 0.14 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2003 ▶) T min = 0.804, T max = 0.922

12928 measured reflections

1758 independent reflections

1538 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.078

S = 1.07

1758 reflections

92 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.28 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor 1997 ▶), SCALEPACK and SORTAV (Blessing, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810035154/jj2050sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035154/jj2050Isup2.hkl

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

C6H4Cl2OS	F(000) = 784
Mr = 195.05	Dx = 1.688 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 12696 reflections
a = 13.0980 (3) Å	θ = 2.9–27.5°
b = 7.1790 (1) Å	µ = 1.04 mm−1
c = 16.3290 (3) Å	T = 120 K
V = 1535.42 (5) Å3	Cut block, colourless
Z = 8	0.22 × 0.14 × 0.08 mm

Nonius KappaCCD diffractometer	1758 independent reflections
Radiation source: fine-focus sealed tube	1538 reflections with I > 2σ(I)
graphite	Rint = 0.050
ω and φ scans	θmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −17→17
Tmin = 0.804, Tmax = 0.922	k = −9→9
12928 measured reflections	l = −21→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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0196P)2 + 1.1699P] where P = (Fo2 + 2Fc2)/3
1758 reflections	(Δ/σ)max = 0.002
92 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.28 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
C1	0.36993 (13)	0.4974 (3)	0.44792 (10)	0.0181 (4)
C2	0.36763 (13)	0.5824 (2)	0.52170 (11)	0.0178 (4)
H2	0.3618	0.7134	0.5285	0.021*
C3	0.37494 (12)	0.4537 (2)	0.58881 (10)	0.0153 (4)
C4	0.38165 (13)	0.2736 (2)	0.56061 (11)	0.0172 (4)
C5	0.37563 (13)	0.5245 (3)	0.67461 (11)	0.0181 (4)
C6	0.37733 (14)	0.3927 (3)	0.74569 (11)	0.0227 (4)
H6A	0.3730	0.4634	0.7969	0.034*
H6B	0.4410	0.3210	0.7448	0.034*
H6C	0.3191	0.3074	0.7418	0.034*
O1	0.37515 (11)	0.69263 (19)	0.68546 (8)	0.0299 (3)
S1	0.38011 (3)	0.25777 (6)	0.45563 (3)	0.02062 (14)
Cl1	0.36483 (4)	0.60020 (7)	0.35316 (3)	0.02524 (14)
Cl2	0.39243 (4)	0.06821 (6)	0.61358 (3)	0.02400 (14)

	U11	U22	U33	U12	U13	U23
C1	0.0175 (9)	0.0234 (10)	0.0134 (9)	−0.0004 (7)	−0.0011 (6)	0.0017 (7)
C2	0.0191 (9)	0.0176 (8)	0.0168 (9)	0.0001 (7)	0.0000 (7)	0.0017 (7)
C3	0.0154 (8)	0.0162 (8)	0.0144 (9)	0.0004 (6)	0.0010 (6)	0.0010 (7)
C4	0.0174 (9)	0.0179 (8)	0.0163 (8)	−0.0007 (7)	0.0008 (7)	0.0006 (7)
C5	0.0190 (9)	0.0198 (8)	0.0154 (9)	0.0003 (7)	0.0005 (6)	−0.0007 (7)
C6	0.0310 (11)	0.0227 (10)	0.0145 (10)	0.0001 (7)	0.0021 (7)	0.0022 (7)
O1	0.0548 (10)	0.0174 (7)	0.0175 (7)	0.0006 (6)	−0.0007 (6)	−0.0024 (6)
S1	0.0244 (3)	0.0215 (3)	0.0160 (3)	−0.00193 (17)	0.00004 (17)	−0.00486 (17)
Cl1	0.0251 (3)	0.0372 (3)	0.0134 (2)	0.00171 (19)	−0.00100 (16)	0.00583 (18)
Cl2	0.0332 (3)	0.0138 (2)	0.0250 (3)	0.00051 (17)	−0.00035 (19)	0.00208 (17)

C1—C2	1.351 (2)	C4—Cl2	1.7151 (18)
C1—Cl1	1.7156 (18)	C4—S1	1.7181 (19)
C1—S1	1.7303 (19)	C5—O1	1.220 (2)
C2—C3	1.437 (2)	C5—C6	1.498 (2)
C2—H2	0.9500	C6—H6A	0.9800
C3—C4	1.376 (2)	C6—H6B	0.9800
C3—C5	1.490 (2)	C6—H6C	0.9800
C2—C1—Cl1	127.54 (15)	Cl2—C4—S1	116.58 (10)
C2—C1—S1	112.71 (13)	O1—C5—C3	118.28 (16)
Cl1—C1—S1	119.75 (10)	O1—C5—C6	120.83 (16)
C1—C2—C3	112.84 (16)	C3—C5—C6	120.88 (16)
C1—C2—H2	123.6	C5—C6—H6A	109.5
C3—C2—H2	123.6	C5—C6—H6B	109.5
C4—C3—C2	110.71 (15)	H6A—C6—H6B	109.5
C4—C3—C5	129.40 (16)	C5—C6—H6C	109.5
C2—C3—C5	119.88 (15)	H6A—C6—H6C	109.5
C3—C4—Cl2	130.13 (14)	H6B—C6—H6C	109.5
C3—C4—S1	113.28 (13)	C4—S1—C1	90.45 (8)
Cl1—C1—C2—C3	−179.10 (13)	C4—C3—C5—O1	175.49 (17)
S1—C1—C2—C3	0.4 (2)	C2—C3—C5—O1	−3.7 (3)
C1—C2—C3—C4	−0.5 (2)	C4—C3—C5—C6	−4.2 (3)
C1—C2—C3—C5	178.80 (15)	C2—C3—C5—C6	176.57 (15)
C2—C3—C4—Cl2	179.62 (14)	C3—C4—S1—C1	−0.14 (14)
C5—C3—C4—Cl2	0.4 (3)	Cl2—C4—S1—C1	−179.47 (11)
C2—C3—C4—S1	0.40 (19)	C2—C1—S1—C4	−0.18 (14)
C5—C3—C4—S1	−178.85 (14)	Cl1—C1—S1—C4	179.40 (11)