(E)-1-(2,5-Dichloro-3-thien-yl)-3-[4-(dimethyl-amino)phen-yl]prop-2-en-1-one.

In the title compound, C(15)H(13)Cl(2)NOS, the benzene and thio-phene rings make a dihedral angle of 10.8 (1)°. The dimethyl-amino substituent and the α,β-unsaturated carbonyl group are almost coplanar with respect to the aromatic ring, forming dihedral angles of 4.73 (3)° and 5.0 (2)°, respectively. In the crystal structure, mol-ecules are connected into two-dimensional layers by weak C-H⋯Cl hydrogen bonds and C-Cl⋯O [Cl⋯O = 3.073 (2) Å] inter-actions. These layers are stacked with short C(meth-yl)-H⋯π contacts betweeen the layers.

Related literature

For applications of chalcone derivatives, see: Indira et al. (2002 ▶); Sarojini et al. (2006 ▶); Tomar et al. (2007 ▶).

Experimental

Crystal data

C15H13Cl2NOS

M = 326.22

Triclinic,

a = 7.2637 (9) Å

b = 8.1136 (9) Å

c = 13.478 (2) Å

α = 89.011 (9)°

β = 79.71 (1)°

γ = 73.07 (1)°

V = 747.2 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.57 mm−1

T = 295 K

0.6 × 0.3 × 0.3 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with an Eos detector

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.785, T max = 1.000

8710 measured reflections

3152 independent reflections

2403 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.109

S = 1.10

3152 reflections

184 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.40 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: Stereochemical Workstation Operation Manual (Siemens, 1989 ▶) and SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810014364/im2193sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014364/im2193Isup2.hkl

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

C15H13Cl2NOS	Z = 2
Mr = 326.22	F(000) = 336
Triclinic, P1	Dx = 1.450 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2637 (9) Å	Cell parameters from 5611 reflections
b = 8.1136 (9) Å	θ = 2.6–28.2°
c = 13.478 (2) Å	µ = 0.57 mm−1
α = 89.011 (9)°	T = 295 K
β = 79.71 (1)°	Block, yellow
γ = 73.07 (1)°	0.6 × 0.3 × 0.3 mm
V = 747.2 (2) Å3

Oxford Diffraction Xcalibur diffractometer with an Eos detector	3152 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2403 reflections with I > 2σ(I)
graphite	Rint = 0.018
Detector resolution: 16.1544 pixels mm-1	θmax = 28.3°, θmin = 2.6°
ω scan	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −10→10
Tmin = 0.785, Tmax = 1.000	l = −17→17
8710 measured reflections

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) = 0.109	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0546P)2 + 0.1725P] where P = (Fo2 + 2Fc2)/3
3152 reflections	(Δ/σ)max = 0.001
184 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.40 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
S1	0.67788 (8)	0.11979 (8)	1.11606 (4)	0.05238 (18)
Cl2	0.49256 (8)	0.25700 (9)	0.94627 (4)	0.0620 (2)
C2	0.6887 (3)	0.2294 (3)	1.00611 (14)	0.0407 (4)
C3	0.8555 (3)	0.2780 (2)	0.98033 (14)	0.0383 (4)
C4	0.9777 (3)	0.2234 (3)	1.05438 (15)	0.0431 (5)
H4A	1.0980	0.2443	1.0507	0.052*
Cl5	1.00237 (10)	0.05512 (9)	1.23148 (4)	0.0699 (2)
C5	0.9014 (3)	0.1398 (3)	1.12908 (15)	0.0454 (5)
C6	0.9255 (3)	0.3667 (3)	0.89011 (15)	0.0432 (5)
O6	1.0970 (2)	0.3669 (2)	0.87491 (13)	0.0636 (5)
C7	0.7927 (3)	0.4499 (3)	0.82226 (16)	0.0473 (5)
H7A	0.6621	0.4519	0.8378	0.057*
C8	0.8548 (3)	0.5232 (3)	0.73845 (16)	0.0456 (5)
H8A	0.9845	0.5242	0.7283	0.055*
C9	0.7452 (3)	0.6010 (2)	0.66156 (15)	0.0412 (4)
C10	0.5490 (3)	0.6086 (3)	0.66361 (15)	0.0435 (5)
H10A	0.4820	0.5665	0.7188	0.052*
C11	0.4534 (3)	0.6765 (3)	0.58656 (15)	0.0435 (5)
H11A	0.3233	0.6795	0.5908	0.052*
C12	0.5478 (3)	0.7420 (2)	0.50101 (14)	0.0399 (4)
C13	0.7440 (3)	0.7332 (3)	0.49862 (16)	0.0489 (5)
H13A	0.8125	0.7735	0.4432	0.059*
C14	0.8364 (3)	0.6662 (3)	0.57683 (16)	0.0500 (5)
H14A	0.9662	0.6641	0.5731	0.060*
N15	0.4527 (3)	0.8088 (2)	0.42422 (14)	0.0527 (5)
C16	0.2469 (4)	0.8283 (3)	0.4313 (2)	0.0669 (7)
H16A	0.2267	0.7165	0.4308	0.100*
H16B	0.2015	0.8906	0.3749	0.100*
H16C	0.1756	0.8906	0.4929	0.100*
C17	0.5519 (4)	0.8642 (4)	0.33356 (17)	0.0657 (7)
H17A	0.5962	0.9594	0.3497	0.098*
H17B	0.4636	0.8996	0.2868	0.098*
H17C	0.6623	0.7707	0.3037	0.098*

	U11	U22	U33	U12	U13	U23
S1	0.0501 (3)	0.0691 (4)	0.0431 (3)	−0.0253 (3)	−0.0097 (2)	0.0124 (3)
Cl2	0.0468 (3)	0.0961 (5)	0.0581 (4)	−0.0360 (3)	−0.0242 (3)	0.0189 (3)
C2	0.0371 (10)	0.0488 (11)	0.0378 (10)	−0.0123 (9)	−0.0117 (8)	0.0027 (8)
C3	0.0376 (10)	0.0399 (10)	0.0387 (10)	−0.0103 (8)	−0.0124 (8)	0.0024 (8)
C4	0.0383 (10)	0.0475 (12)	0.0464 (11)	−0.0125 (9)	−0.0160 (9)	0.0042 (9)
Cl5	0.0750 (4)	0.0881 (5)	0.0490 (3)	−0.0178 (3)	−0.0300 (3)	0.0209 (3)
C5	0.0479 (11)	0.0516 (12)	0.0372 (10)	−0.0104 (9)	−0.0162 (9)	0.0060 (9)
C6	0.0400 (10)	0.0458 (11)	0.0467 (11)	−0.0139 (9)	−0.0138 (9)	0.0059 (9)
O6	0.0461 (9)	0.0881 (12)	0.0681 (11)	−0.0317 (8)	−0.0226 (8)	0.0325 (9)
C7	0.0437 (11)	0.0525 (12)	0.0500 (12)	−0.0165 (10)	−0.0170 (9)	0.0138 (10)
C8	0.0436 (11)	0.0482 (12)	0.0490 (12)	−0.0165 (9)	−0.0139 (9)	0.0072 (9)
C9	0.0448 (11)	0.0398 (11)	0.0408 (10)	−0.0144 (9)	−0.0091 (8)	0.0057 (8)
C10	0.0447 (11)	0.0474 (12)	0.0389 (10)	−0.0165 (9)	−0.0046 (8)	0.0086 (9)
C11	0.0382 (10)	0.0496 (12)	0.0436 (11)	−0.0148 (9)	−0.0078 (8)	0.0083 (9)
C12	0.0451 (11)	0.0370 (10)	0.0379 (10)	−0.0119 (8)	−0.0085 (8)	0.0044 (8)
C13	0.0474 (12)	0.0568 (13)	0.0456 (12)	−0.0226 (10)	−0.0054 (9)	0.0145 (10)
C14	0.0404 (11)	0.0612 (14)	0.0528 (13)	−0.0217 (10)	−0.0098 (9)	0.0138 (10)
N15	0.0540 (11)	0.0618 (12)	0.0466 (10)	−0.0205 (9)	−0.0163 (8)	0.0205 (8)
C16	0.0601 (15)	0.0778 (17)	0.0707 (16)	−0.0228 (13)	−0.0302 (13)	0.0236 (13)
C17	0.0734 (17)	0.0800 (17)	0.0454 (13)	−0.0247 (14)	−0.0132 (12)	0.0191 (12)

S1—C2	1.717 (2)	C10—C11	1.371 (3)
S1—C5	1.717 (2)	C10—H10A	0.9300
Cl2—C2	1.7175 (19)	C11—C12	1.411 (3)
C2—C3	1.366 (3)	C11—H11A	0.9300
C3—C4	1.433 (3)	C12—N15	1.364 (3)
C3—C6	1.489 (3)	C12—C13	1.401 (3)
C4—C5	1.333 (3)	C13—C14	1.371 (3)
C4—H4A	0.9300	C13—H13A	0.9300
Cl5—C5	1.718 (2)	C14—H14A	0.9300
C6—O6	1.226 (2)	N15—C17	1.439 (3)
C6—C7	1.462 (3)	N15—C16	1.443 (3)
C7—C8	1.335 (3)	C16—H16A	0.9600
C7—H7A	0.9300	C16—H16B	0.9600
C8—C9	1.444 (3)	C16—H16C	0.9600
C8—H8A	0.9300	C17—H17A	0.9600
C9—C14	1.391 (3)	C17—H17B	0.9600
C9—C10	1.403 (3)	C17—H17C	0.9600
C2—S1—C5	89.86 (10)	C10—C11—C12	121.54 (19)
C3—C2—S1	113.70 (14)	C10—C11—H11A	119.2
C3—C2—Cl2	130.86 (16)	C12—C11—H11A	119.2
S1—C2—Cl2	115.43 (11)	N15—C12—C13	121.88 (18)
C2—C3—C4	110.04 (18)	N15—C12—C11	121.47 (19)
C2—C3—C6	130.73 (17)	C13—C12—C11	116.65 (18)
C4—C3—C6	119.18 (17)	C14—C13—C12	120.89 (19)
C5—C4—C3	113.12 (18)	C14—C13—H13A	119.6
C5—C4—H4A	123.4	C12—C13—H13A	119.6
C3—C4—H4A	123.4	C13—C14—C9	123.04 (19)
C4—C5—S1	113.29 (15)	C13—C14—H14A	118.5
C4—C5—Cl5	127.12 (17)	C9—C14—H14A	118.5
S1—C5—Cl5	119.59 (13)	C12—N15—C17	121.73 (19)
O6—C6—C7	121.58 (19)	C12—N15—C16	121.05 (19)
O6—C6—C3	117.89 (17)	C17—N15—C16	117.22 (19)
C7—C6—C3	120.54 (17)	N15—C16—H16A	109.5
C8—C7—C6	121.49 (19)	N15—C16—H16B	109.5
C8—C7—H7A	119.3	H16A—C16—H16B	109.5
C6—C7—H7A	119.3	N15—C16—H16C	109.5
C7—C8—C9	127.96 (19)	H16A—C16—H16C	109.5
C7—C8—H8A	116.0	H16B—C16—H16C	109.5
C9—C8—H8A	116.0	N15—C17—H17A	109.5
C14—C9—C10	116.05 (18)	N15—C17—H17B	109.5
C14—C9—C8	120.06 (18)	H17A—C17—H17B	109.5
C10—C9—C8	123.80 (18)	N15—C17—H17C	109.5
C11—C10—C9	121.81 (18)	H17A—C17—H17C	109.5
C11—C10—H10A	119.1	H17B—C17—H17C	109.5
C9—C10—H10A	119.1
C5—S1—C2—C3	0.36 (17)	C6—C7—C8—C9	176.1 (2)
C5—S1—C2—Cl2	179.45 (13)	C7—C8—C9—C14	−177.7 (2)
S1—C2—C3—C4	−0.3 (2)	C7—C8—C9—C10	−1.0 (4)
Cl2—C2—C3—C4	−179.25 (16)	C14—C9—C10—C11	0.0 (3)
S1—C2—C3—C6	176.89 (17)	C8—C9—C10—C11	−176.8 (2)
Cl2—C2—C3—C6	−2.0 (4)	C9—C10—C11—C12	0.1 (3)
C2—C3—C4—C5	0.1 (3)	C10—C11—C12—N15	179.72 (19)
C6—C3—C4—C5	−177.47 (18)	C10—C11—C12—C13	0.3 (3)
C3—C4—C5—S1	0.1 (2)	N15—C12—C13—C14	179.7 (2)
C3—C4—C5—Cl5	−179.88 (15)	C11—C12—C13—C14	−0.9 (3)
C2—S1—C5—C4	−0.28 (18)	C12—C13—C14—C9	1.0 (4)
C2—S1—C5—Cl5	179.74 (14)	C10—C9—C14—C13	−0.5 (3)
C2—C3—C6—O6	−166.3 (2)	C8—C9—C14—C13	176.4 (2)
C4—C3—C6—O6	10.7 (3)	C13—C12—N15—C17	4.0 (3)
C2—C3—C6—C7	13.5 (3)	C11—C12—N15—C17	−175.4 (2)
C4—C3—C6—C7	−169.47 (18)	C13—C12—N15—C16	−175.5 (2)
O6—C6—C7—C8	3.0 (3)	C11—C12—N15—C16	5.2 (3)
C3—C6—C7—C8	−176.8 (2)

Cg is the centroid of the phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16B···Cl5i	0.96	2.72	3.664 (2)	168
C16—H16A···Cgii	0.96	3.01	3.899 (3)	155

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16B⋯Cl5i	0.96	2.72	3.664 (2)	168
C16—H16A⋯Cgii	0.96	3.01	3.899 (3)	155

Symmetry codes: (i) ; (ii) .