(2E)-1-(5-Chloro-thio-phen-2-yl)-3-(2,3-dimeth-oxy-phen-yl)prop-2-en-1-one.

In the title compound, C(15)H(13)ClO(3)S, the chloro-thio-phene and dimeth-oxy-phenyl groups are linked by a prop-2-en-1-one group. The C=C double bond exhibits an E conformation. The mol-ecule is non-planar, with a dihedral angle of 31.12 (5)° between the chloro-thio-phene and dimeth-oxy-phenyl rings. The meth-oxy group at position 3 is coplanar with the benzene ring to which it is attached, with a C-O-C-C torsion angle of -3.8 (3)°. The meth-oxy group attached at position 2 of the benzene ring is in a (+)synclinal conformation, as indicated by the C-O-C-C torsion angle of -73.6 (2)°. In the crystal, two different C-H⋯O inter-molecular inter-actions generate chains of mol-ecules extending along the b axis.

Related literature

For general background to chalcones and their biological properties, see: Choudary et al. (1999 ▶); Tomazela et al. (2000 ▶). For a related structure, see: Benmekhbi et al. (2009 ▶).

Experimental

Crystal data

C15H13ClO3S

M = 308.76

Monoclinic,

a = 11.6139 (8) Å

b = 8.5605 (5) Å

c = 14.4174 (9) Å

β = 99.907 (2)°

V = 1412.02 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.42 mm−1

T = 296 K

0.20 × 0.18 × 0.16 mm

Data collection

Bruker SMART APEX CCD detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.920, T max = 0.936

9286 measured reflections

3087 independent reflections

2348 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.102

S = 1.07

3087 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and CAMERON (Watkin et al., 1996 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811037135/pv2439sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037135/pv2439Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811037135/pv2439Isup3.cml

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

C15H13ClO3S	F(000) = 640
Mr = 308.76	Dx = 1.452 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3087 reflections
a = 11.6139 (8) Å	θ = 1.8–27.0°
b = 8.5605 (5) Å	µ = 0.42 mm−1
c = 14.4174 (9) Å	T = 296 K
β = 99.907 (2)°	Block, yellow
V = 1412.02 (16) Å3	0.20 × 0.18 × 0.16 mm
Z = 4

Bruker SMART APEX CCD detector diffractometer	3087 independent reflections
Radiation source: fine-focus sealed tube	2348 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω scans	θmax = 27.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −14→14
Tmin = 0.920, Tmax = 0.936	k = −8→10
9286 measured reflections	l = −18→14

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0494P)2 + 0.1854P] where P = (Fo2 + 2Fc2)/3
3087 reflections	(Δ/σ)max = 0.001
183 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.22862 (5)	0.40719 (7)	1.17836 (4)	0.06157 (19)
S1	0.33583 (4)	0.57846 (6)	1.03539 (3)	0.04070 (15)
O1	0.46583 (12)	0.75106 (18)	0.91191 (10)	0.0540 (4)
O2	0.80027 (11)	0.99907 (15)	0.81682 (8)	0.0413 (3)
O3	0.97557 (11)	1.20940 (17)	0.83929 (10)	0.0509 (4)
C1	0.33815 (16)	0.5228 (2)	1.14971 (13)	0.0387 (4)
C2	0.43004 (17)	0.5799 (2)	1.21037 (13)	0.0451 (5)
H2	0.4440	0.5608	1.2748	0.054*
C3	0.50212 (16)	0.6722 (2)	1.16311 (13)	0.0427 (5)
H3	0.5697	0.7210	1.1936	0.051*
C4	0.46355 (14)	0.6834 (2)	1.06827 (12)	0.0358 (4)
C5	0.51284 (15)	0.7641 (2)	0.99432 (13)	0.0384 (4)
C6	0.61819 (15)	0.8604 (2)	1.02313 (13)	0.0407 (4)
H6	0.6442	0.8791	1.0868	0.049*
C7	0.67724 (15)	0.9214 (2)	0.96006 (13)	0.0382 (4)
H7	0.6509	0.8949	0.8975	0.046*
C8	0.77860 (15)	1.0250 (2)	0.97828 (12)	0.0357 (4)
C9	0.82092 (16)	1.0873 (2)	1.06805 (13)	0.0431 (5)
H9	0.7857	1.0592	1.1188	0.052*
C10	0.91330 (17)	1.1886 (3)	1.08140 (14)	0.0485 (5)
H10	0.9406	1.2280	1.1413	0.058*
C11	0.96713 (16)	1.2336 (2)	1.00634 (14)	0.0466 (5)
H11	1.0293	1.3036	1.0161	0.056*
C12	0.92801 (15)	1.1742 (2)	0.91742 (13)	0.0396 (4)
C13	0.83426 (15)	1.0682 (2)	0.90333 (12)	0.0347 (4)
C14	0.73927 (19)	1.0981 (3)	0.74504 (15)	0.0540 (6)
H14C	0.6614	1.1159	0.7566	0.081*
H14B	0.7358	1.0488	0.6848	0.081*
H14A	0.7796	1.1960	0.7454	0.081*
C15	1.0673 (2)	1.3220 (3)	0.84993 (18)	0.0660 (7)
H15C	1.0407	1.4174	0.8742	0.099*
H15A	1.0896	1.3416	0.7899	0.099*
H15B	1.1334	1.2829	0.8929	0.099*

	U11	U22	U33	U12	U13	U23
Cl1	0.0603 (3)	0.0672 (4)	0.0591 (4)	−0.0213 (3)	0.0158 (3)	0.0057 (3)
S1	0.0417 (3)	0.0445 (3)	0.0344 (3)	−0.00324 (19)	0.00221 (18)	0.0015 (2)
O1	0.0592 (8)	0.0645 (10)	0.0361 (8)	−0.0086 (7)	0.0025 (6)	0.0093 (7)
O2	0.0537 (7)	0.0392 (8)	0.0328 (7)	0.0012 (6)	0.0124 (6)	−0.0022 (6)
O3	0.0484 (8)	0.0632 (10)	0.0446 (8)	−0.0134 (7)	0.0174 (6)	0.0012 (7)
C1	0.0436 (10)	0.0360 (10)	0.0382 (10)	−0.0011 (8)	0.0122 (8)	0.0004 (8)
C2	0.0542 (11)	0.0497 (13)	0.0315 (9)	−0.0044 (9)	0.0074 (8)	−0.0008 (9)
C3	0.0438 (10)	0.0453 (12)	0.0374 (10)	−0.0059 (8)	0.0026 (8)	−0.0015 (9)
C4	0.0362 (9)	0.0339 (10)	0.0377 (10)	0.0025 (7)	0.0078 (7)	−0.0004 (8)
C5	0.0405 (9)	0.0382 (11)	0.0370 (10)	0.0060 (8)	0.0084 (8)	0.0046 (8)
C6	0.0443 (10)	0.0441 (11)	0.0343 (10)	−0.0009 (8)	0.0087 (8)	0.0013 (8)
C7	0.0438 (10)	0.0370 (11)	0.0349 (9)	0.0048 (8)	0.0101 (8)	0.0029 (8)
C8	0.0373 (9)	0.0365 (10)	0.0339 (9)	0.0061 (7)	0.0078 (7)	0.0024 (8)
C9	0.0453 (10)	0.0518 (13)	0.0333 (9)	0.0036 (9)	0.0100 (8)	0.0032 (9)
C10	0.0472 (11)	0.0616 (14)	0.0350 (10)	0.0001 (10)	0.0019 (8)	−0.0040 (9)
C11	0.0388 (10)	0.0536 (13)	0.0462 (12)	−0.0048 (8)	0.0042 (8)	−0.0020 (10)
C12	0.0374 (9)	0.0438 (12)	0.0394 (10)	0.0033 (8)	0.0116 (8)	0.0039 (9)
C13	0.0381 (9)	0.0337 (10)	0.0332 (9)	0.0049 (7)	0.0083 (7)	−0.0010 (8)
C14	0.0607 (13)	0.0573 (14)	0.0412 (11)	0.0048 (10)	0.0009 (9)	0.0042 (10)
C15	0.0583 (13)	0.0776 (18)	0.0665 (16)	−0.0211 (12)	0.0230 (11)	0.0056 (13)

Cl1—C1	1.7173 (19)	C7—C8	1.461 (3)
S1—C1	1.7115 (19)	C7—H7	0.9300
S1—C4	1.7292 (18)	C8—C13	1.401 (2)
O1—C5	1.224 (2)	C8—C9	1.408 (3)
O2—C13	1.376 (2)	C9—C10	1.367 (3)
O2—C14	1.428 (2)	C9—H9	0.9300
O3—C12	1.371 (2)	C10—C11	1.394 (3)
O3—C15	1.425 (2)	C10—H10	0.9300
C1—C2	1.350 (3)	C11—C12	1.381 (3)
C2—C3	1.409 (3)	C11—H11	0.9300
C2—H2	0.9300	C12—C13	1.405 (3)
C3—C4	1.367 (2)	C14—H14C	0.9600
C3—H3	0.9300	C14—H14B	0.9600
C4—C5	1.467 (2)	C14—H14A	0.9600
C5—C6	1.474 (3)	C15—H15C	0.9600
C6—C7	1.336 (3)	C15—H15A	0.9600
C6—H6	0.9300	C15—H15B	0.9600
C1—S1—C4	90.57 (9)	C10—C9—C8	120.74 (18)
C13—O2—C14	115.51 (15)	C10—C9—H9	119.6
C12—O3—C15	117.37 (17)	C8—C9—H9	119.6
C2—C1—S1	113.76 (14)	C9—C10—C11	120.79 (18)
C2—C1—Cl1	126.07 (15)	C9—C10—H10	119.6
S1—C1—Cl1	120.16 (11)	C11—C10—H10	119.6
C1—C2—C3	111.04 (17)	C12—C11—C10	119.92 (19)
C1—C2—H2	124.5	C12—C11—H11	120.0
C3—C2—H2	124.5	C10—C11—H11	120.0
C4—C3—C2	113.79 (17)	O3—C12—C11	124.53 (17)
C4—C3—H3	123.1	O3—C12—C13	115.79 (16)
C2—C3—H3	123.1	C11—C12—C13	119.67 (17)
C3—C4—C5	131.18 (17)	O2—C13—C8	119.14 (16)
C3—C4—S1	110.84 (14)	O2—C13—C12	120.23 (16)
C5—C4—S1	117.97 (13)	C8—C13—C12	120.53 (17)
O1—C5—C4	119.86 (17)	O2—C14—H14C	109.5
O1—C5—C6	122.29 (18)	O2—C14—H14B	109.5
C4—C5—C6	117.85 (16)	H14C—C14—H14B	109.5
C7—C6—C5	121.68 (17)	O2—C14—H14A	109.5
C7—C6—H6	119.2	H14C—C14—H14A	109.5
C5—C6—H6	119.2	H14B—C14—H14A	109.5
C6—C7—C8	127.37 (18)	O3—C15—H15C	109.5
C6—C7—H7	116.3	O3—C15—H15A	109.5
C8—C7—H7	116.3	H15C—C15—H15A	109.5
C13—C8—C9	118.32 (17)	O3—C15—H15B	109.5
C13—C8—C7	119.08 (16)	H15C—C15—H15B	109.5
C9—C8—C7	122.57 (17)	H15A—C15—H15B	109.5
C4—S1—C1—C2	0.09 (17)	C13—C8—C9—C10	0.6 (3)
C4—S1—C1—Cl1	179.16 (12)	C7—C8—C9—C10	−177.48 (18)
S1—C1—C2—C3	−0.1 (2)	C8—C9—C10—C11	0.5 (3)
Cl1—C1—C2—C3	−179.14 (15)	C9—C10—C11—C12	−0.8 (3)
C1—C2—C3—C4	0.1 (3)	C15—O3—C12—C11	−3.8 (3)
C2—C3—C4—C5	−178.76 (19)	C15—O3—C12—C13	177.16 (18)
C2—C3—C4—S1	−0.1 (2)	C10—C11—C12—O3	−179.22 (18)
C1—S1—C4—C3	−0.02 (15)	C10—C11—C12—C13	−0.2 (3)
C1—S1—C4—C5	178.87 (15)	C14—O2—C13—C8	109.94 (19)
C3—C4—C5—O1	176.0 (2)	C14—O2—C13—C12	−73.6 (2)
S1—C4—C5—O1	−2.6 (2)	C9—C8—C13—O2	174.84 (15)
C3—C4—C5—C6	−4.6 (3)	C7—C8—C13—O2	−7.0 (2)
S1—C4—C5—C6	176.79 (13)	C9—C8—C13—C12	−1.6 (3)
O1—C5—C6—C7	−9.3 (3)	C7—C8—C13—C12	176.61 (16)
C4—C5—C6—C7	171.31 (17)	O3—C12—C13—O2	4.1 (3)
C5—C6—C7—C8	176.47 (17)	C11—C12—C13—O2	−175.02 (16)
C6—C7—C8—C13	175.42 (18)	O3—C12—C13—C8	−179.52 (16)
C6—C7—C8—C9	−6.5 (3)	C11—C12—C13—C8	1.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1i	0.93	2.53	3.209 (2)	130
C15—H15A···O2ii	0.96	2.55	3.423 (3)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.93	2.53	3.209 (2)	130
C15—H15A⋯O2ii	0.96	2.55	3.423 (3)	151

Symmetry codes: (i) ; (ii) .