(E)-3-(2,4-Dichloro-phen-yl)-1-(2-thien-yl)prop-2-en-1-one.

In the title chalcone derivative, C(13)H(8)Cl(2)OS, the prop-2-en-1-one unit and the thio-phene and 2,4-dichloro-phenyl rings are each essentially planar. The inter-planar angle between the thio-phene and 2,4-dichloro-phenyl rings is 19.87 (6)°. Weak intra-molecular C-H⋯O and C-H⋯Cl inter-actions involving the prop-2-en-1-one unit generate an S(5)S(5) ring motif. In the crystal structure, mol-ecules are linked into head-to-tail zigzag chains along the a axis and adjacent chains are cross-linked. These cross-linked chains are arranged into sheets parallel to the ab plane. The crystal structure is stabilized by weak C-H⋯O, C-H⋯Cl and C-H⋯π inter-actions. A π-π inter-action was also observed with a centroid-centroid distance of 3.6845 (6) Å.

Related literature

For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For related structures, see, for example: Fun et al. (2008a ▶,b ▶). For background on the applications of substituted chalcones, see, for example: Agrinskaya et al. (1999 ▶); Chopra et al. (2007 ▶); Goto et al. (1991 ▶); Gu et al. (2008a ▶,b ▶,c ▶); Patil et al. (2007a ▶,b ▶,c ▶); Sarojini et al. (2006 ▶); Wang et al. (2004 ▶).

Experimental

Crystal data

C13H8Cl2OS

M = 283.16

Monoclinic,

a = 9.5701 (4) Å

b = 13.9544 (6) Å

c = 10.4748 (4) Å

β = 118.735 (3)°

V = 1226.59 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.68 mm−1

T = 100.0 (1) K

0.58 × 0.24 × 0.13 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.695, T max = 0.919

41878 measured reflections

4435 independent reflections

3831 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.082

S = 1.06

4435 reflections

162 parameters

H-atom parameters constrained

Δρmax = 0.60 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808026524/ww2127sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026524/ww2127Isup2.hkl

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

C13H8Cl2OS	F000 = 576
Mr = 283.16	Dx = 1.533 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4435 reflections
a = 9.5701 (4) Å	θ = 2.4–32.5º
b = 13.9544 (6) Å	µ = 0.68 mm−1
c = 10.4748 (4) Å	T = 100.0 (1) K
β = 118.735 (3)º	Needle, colorless
V = 1226.59 (9) Å3	0.58 × 0.24 × 0.13 mm
Z = 4

Bruker SMART APEX2 CCD area-detector diffractometer	4435 independent reflections
Radiation source: fine-focus sealed tube	3831 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.031
Detector resolution: 8.33 pixels mm-1	θmax = 32.5º
T = 100.0(1) K	θmin = 2.4º
ω scans	h = −14→14
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −21→21
Tmin = 0.695, Tmax = 0.919	l = −15→15
41878 measured reflections

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)] = 0.029	H-atom parameters constrained
wR(F2) = 0.082	w = 1/[σ2(Fo2) + (0.0403P)2 + 0.4876P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
4435 reflections	Δρmax = 0.60 e Å−3
162 parameters	Δρmin = −0.28 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
Cl1	−0.05796 (3)	0.558919 (18)	0.18442 (3)	0.01990 (7)
Cl2	−0.34903 (3)	0.43921 (2)	0.48214 (3)	0.02181 (7)
S1	0.55248 (3)	0.18039 (2)	0.20853 (3)	0.02097 (7)
O1	0.30678 (11)	0.32994 (6)	0.13125 (9)	0.02122 (16)
C1	0.64865 (14)	0.08866 (9)	0.32542 (13)	0.0239 (2)
H1A	0.7245	0.0504	0.3162	0.042 (5)*
C2	0.60409 (14)	0.07946 (9)	0.43128 (13)	0.0222 (2)
H2A	0.6448	0.0331	0.5039	0.030 (4)*
C3	0.48923 (13)	0.14851 (8)	0.41751 (12)	0.01776 (19)
H3A	0.4462	0.1531	0.4802	0.025 (4)*
C4	0.44866 (12)	0.20851 (7)	0.29930 (11)	0.01483 (17)
C5	0.32870 (12)	0.28469 (7)	0.24030 (11)	0.01551 (18)
C6	0.23178 (13)	0.30140 (8)	0.31373 (11)	0.01662 (18)
H6A	0.2532	0.2670	0.3972	0.033 (4)*
C7	0.11366 (13)	0.36566 (7)	0.26054 (12)	0.01658 (18)
H7A	0.0995	0.4012	0.1800	0.022 (4)*
C8	0.00490 (12)	0.38454 (7)	0.31897 (11)	0.01508 (17)
C9	−0.01998 (13)	0.31711 (8)	0.40561 (12)	0.01814 (19)
H9A	0.0373	0.2601	0.4292	0.032 (4)*
C10	−0.12712 (13)	0.33288 (8)	0.45700 (12)	0.01822 (19)
H10A	−0.1418	0.2872	0.5141	0.030 (4)*
C11	−0.21239 (12)	0.41837 (8)	0.42150 (12)	0.01651 (18)
C12	−0.19070 (12)	0.48797 (7)	0.33822 (11)	0.01626 (18)
H12A	−0.2472	0.5453	0.3164	0.023 (4)*
C13	−0.08277 (12)	0.47006 (7)	0.28828 (11)	0.01535 (18)

	U11	U22	U33	U12	U13	U23
Cl1	0.02152 (13)	0.01786 (12)	0.02316 (13)	0.00278 (8)	0.01301 (10)	0.00674 (9)
Cl2	0.02120 (13)	0.02533 (13)	0.02547 (14)	0.00247 (9)	0.01647 (11)	0.00112 (10)
S1	0.02269 (14)	0.02431 (14)	0.02117 (13)	0.00481 (10)	0.01474 (11)	0.00138 (10)
O1	0.0269 (4)	0.0218 (4)	0.0201 (4)	0.0047 (3)	0.0155 (3)	0.0046 (3)
C1	0.0216 (5)	0.0255 (5)	0.0248 (5)	0.0084 (4)	0.0113 (4)	0.0015 (4)
C2	0.0221 (5)	0.0233 (5)	0.0201 (5)	0.0049 (4)	0.0092 (4)	0.0019 (4)
C3	0.0195 (5)	0.0187 (4)	0.0167 (4)	0.0009 (4)	0.0100 (4)	−0.0006 (4)
C4	0.0159 (4)	0.0156 (4)	0.0155 (4)	0.0001 (3)	0.0096 (4)	−0.0013 (3)
C5	0.0176 (4)	0.0152 (4)	0.0154 (4)	−0.0004 (3)	0.0093 (4)	−0.0019 (3)
C6	0.0191 (5)	0.0178 (4)	0.0159 (4)	0.0006 (4)	0.0107 (4)	−0.0001 (3)
C7	0.0191 (4)	0.0160 (4)	0.0178 (4)	0.0001 (3)	0.0114 (4)	−0.0007 (3)
C8	0.0162 (4)	0.0147 (4)	0.0154 (4)	0.0005 (3)	0.0084 (4)	−0.0001 (3)
C9	0.0211 (5)	0.0148 (4)	0.0216 (5)	0.0023 (3)	0.0127 (4)	0.0018 (4)
C10	0.0215 (5)	0.0162 (4)	0.0208 (5)	0.0005 (4)	0.0133 (4)	0.0016 (4)
C11	0.0160 (4)	0.0187 (4)	0.0170 (4)	0.0000 (3)	0.0097 (4)	−0.0015 (3)
C12	0.0155 (4)	0.0162 (4)	0.0173 (4)	0.0018 (3)	0.0081 (4)	0.0006 (3)
C13	0.0158 (4)	0.0148 (4)	0.0154 (4)	−0.0003 (3)	0.0075 (3)	0.0016 (3)

Cl1—C13	1.7396 (10)	C6—C7	1.3367 (15)
Cl2—C11	1.7310 (11)	C6—H6A	0.9300
S1—C1	1.7033 (12)	C7—C8	1.4629 (14)
S1—C4	1.7186 (10)	C7—H7A	0.9300
O1—C5	1.2317 (13)	C8—C13	1.4042 (14)
C1—C2	1.3720 (17)	C8—C9	1.4048 (15)
C1—H1A	0.9425	C9—C10	1.3858 (16)
C2—C3	1.4160 (16)	C9—H9A	0.9300
C2—H2A	0.9300	C10—C11	1.3912 (15)
C3—C4	1.3865 (15)	C10—H10A	0.9301
C3—H3A	0.9302	C11—C12	1.3862 (15)
C4—C5	1.4656 (14)	C12—C13	1.3866 (15)
C5—C6	1.4806 (14)	C12—H12A	0.9299
C1—S1—C4	91.72 (6)	C6—C7—H7A	117.4
C2—C1—S1	112.39 (9)	C8—C7—H7A	117.4
C2—C1—H1A	125.7	C13—C8—C9	116.67 (9)
S1—C1—H1A	121.9	C13—C8—C7	121.62 (9)
C1—C2—C3	112.43 (11)	C9—C8—C7	121.69 (9)
C1—C2—H2A	123.8	C10—C9—C8	122.10 (10)
C3—C2—H2A	123.8	C10—C9—H9A	119.0
C4—C3—C2	111.85 (10)	C8—C9—H9A	118.9
C4—C3—H3A	124.1	C9—C10—C11	118.74 (10)
C2—C3—H3A	124.1	C9—C10—H10A	120.6
C3—C4—C5	129.85 (9)	C11—C10—H10A	120.6
C3—C4—S1	111.60 (8)	C12—C11—C10	121.53 (10)
C5—C4—S1	118.44 (8)	C12—C11—Cl2	118.77 (8)
O1—C5—C4	120.84 (9)	C10—C11—Cl2	119.70 (8)
O1—C5—C6	122.07 (10)	C11—C12—C13	118.37 (10)
C4—C5—C6	117.04 (9)	C11—C12—H12A	120.8
C7—C6—C5	120.30 (10)	C13—C12—H12A	120.8
C7—C6—H6A	119.9	C12—C13—C8	122.57 (9)
C5—C6—H6A	119.8	C12—C13—Cl1	117.25 (8)
C6—C7—C8	125.15 (10)	C8—C13—Cl1	120.18 (8)
C4—S1—C1—C2	−0.23 (10)	C6—C7—C8—C9	−21.13 (17)
S1—C1—C2—C3	−0.06 (14)	C13—C8—C9—C10	0.92 (16)
C1—C2—C3—C4	0.42 (15)	C7—C8—C9—C10	−177.58 (10)
C2—C3—C4—C5	175.55 (11)	C8—C9—C10—C11	−0.07 (17)
C2—C3—C4—S1	−0.59 (12)	C9—C10—C11—C12	−0.93 (17)
C1—S1—C4—C3	0.47 (9)	C9—C10—C11—Cl2	179.10 (9)
C1—S1—C4—C5	−176.16 (9)	C10—C11—C12—C13	0.99 (16)
C3—C4—C5—O1	−178.54 (11)	Cl2—C11—C12—C13	−179.04 (8)
S1—C4—C5—O1	−2.62 (14)	C11—C12—C13—C8	−0.07 (16)
C3—C4—C5—C6	−1.06 (16)	C11—C12—C13—Cl1	−179.86 (8)
S1—C4—C5—C6	174.85 (7)	C9—C8—C13—C12	−0.86 (15)
O1—C5—C6—C7	1.53 (16)	C7—C8—C13—C12	177.65 (10)
C4—C5—C6—C7	−175.91 (10)	C9—C8—C13—Cl1	178.93 (8)
C5—C6—C7—C8	176.55 (10)	C7—C8—C13—Cl1	−2.57 (14)
C6—C7—C8—C13	160.45 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O1i	0.93	2.52	3.4512 (17)	175
C7—H7A···Cl1	0.93	2.68	3.0573 (11)	105
C7—H7A···O1	0.93	2.48	2.8116 (17)	101
C10—H10A···Cg1ii	0.93	3.33	3.8233 (13)	115
C12—H12A···Cg1iii	0.93	2.87	3.6907 (13)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O1i	0.93	2.52	3.4512 (17)	175
C7—H7A⋯Cl1	0.93	2.68	3.0573 (11)	105
C7—H7A⋯O1	0.93	2.48	2.8116 (17)	101
C10—H10A⋯Cg1ii	0.93	3.33	3.8233 (13)	115
C12—H12A⋯Cg1iii	0.93	2.87	3.6907 (13)	148

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of the S1/C1–C4 ring.