(E)-1-(2,5-Dichloro-3-thien-yl)-3-(3,4-dimeth-oxy-phen-yl)prop-2-en-1-one.

In the title compound, C(15)H(12)Cl(2)O(3)S, the prop-2-en-1-one (enone) fragment is almost planar [C-C-C-O = 2.2 (4)°] and it subtends dihedral angles of 11.9 (2) and 11.0 (2)° with the thio-phene and benzene rings, respectively. The dihedral angle between the aromatic rings is 3.47 (16)°. In the crystal, weak C-H⋯O and C-H⋯Cl inter-actions link the mol-ecules, leading to R(2) (2)(14), R(2) (2)(24) and C(11) supra-molecular motifs occurring within the three-dimensional network. Weak aromatic π-π stacking [centroid-centroid separations = 3.6823 (15) and 3.8722 (15) Å] may also help to consolidate the packing.

Related literature

For a related structure and background references, see: Jasinski et al. (2010 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H12Cl2O3S

M = 343.21

Monoclinic,

a = 8.9331 (2) Å

b = 8.9997 (2) Å

c = 18.8210 (5) Å

β = 100.181 (1)°

V = 1489.29 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.58 mm−1

T = 120 K

0.24 × 0.12 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan [SADABS (Bruker, 2003 ▶) and Blessing (1995 ▶)] T min = 0.873, T max = 0.944

22032 measured reflections

3424 independent reflections

2834 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.113

S = 1.10

3424 reflections

193 parameters

H-atom parameters constrained

Δρmax = 0.72 e Å−3

Δρmin = −0.41 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: COLLECT; data reduction: DENZO (Otwinowski & Minor, 1997 ▶); 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: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810035142/ng5014sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035142/ng5014Isup2.hkl

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

C15H12Cl2O3S	F(000) = 704
Mr = 343.21	Dx = 1.531 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 20728 reflections
a = 8.9331 (2) Å	θ = 2.9–27.5°
b = 8.9997 (2) Å	µ = 0.58 mm−1
c = 18.8210 (5) Å	T = 120 K
β = 100.181 (1)°	Fragment, yellow
V = 1489.29 (6) Å3	0.24 × 0.12 × 0.10 mm
Z = 4

Nonius KappaCCD diffractometer	3424 independent reflections
Radiation source: fine-focus sealed tube	2834 reflections with I > 2σ(I)
graphite	Rint = 0.056
ω and φ scans	θmax = 27.6°, θmin = 3.2°
Absorption correction: multi-scan [SADABS (Bruker, 2003) and Blessing (1995)]	h = −11→11
Tmin = 0.873, Tmax = 0.944	k = −11→11
22032 measured reflections	l = −24→24

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)] = 0.048	H-atom parameters constrained
wR(F2) = 0.113	w = 1/[σ2(Fo2) + (0.034P)2 + 1.9239P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
3424 reflections	Δρmax = 0.72 e Å−3
193 parameters	Δρmin = −0.41 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.011 (2)

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	0.4943 (3)	0.2226 (3)	0.72975 (12)	0.0218 (5)
C2	0.5681 (3)	0.2506 (3)	0.67246 (14)	0.0253 (5)
H2	0.6632	0.2050	0.6705	0.030*
C3	0.5013 (3)	0.3471 (3)	0.61723 (14)	0.0273 (5)
H3	0.5512	0.3644	0.5774	0.033*
C4	0.3644 (3)	0.4175 (3)	0.61939 (13)	0.0248 (5)
C5	0.2908 (3)	0.3901 (3)	0.67817 (13)	0.0227 (5)
H5	0.1977	0.4388	0.6809	0.027*
C6	0.3533 (3)	0.2927 (3)	0.73192 (12)	0.0207 (5)
C7	0.2948 (3)	0.5123 (3)	0.55890 (14)	0.0269 (5)
H7	0.3459	0.5142	0.5187	0.032*
C8	0.1686 (3)	0.5971 (3)	0.55235 (13)	0.0232 (5)
H8	0.1154	0.6027	0.5918	0.028*
C9	0.1115 (3)	0.6799 (3)	0.48719 (13)	0.0230 (5)
C10	−0.0865 (3)	0.8706 (3)	0.43372 (13)	0.0217 (5)
C11	−0.0291 (3)	0.7698 (3)	0.48589 (12)	0.0213 (5)
C12	−0.1241 (3)	0.7591 (3)	0.53941 (13)	0.0265 (5)
H12	−0.1035	0.6955	0.5803	0.032*
C13	−0.2457 (3)	0.8490 (3)	0.52538 (14)	0.0298 (6)
C14	0.6852 (3)	0.0533 (3)	0.78546 (16)	0.0382 (7)
H14A	0.7073	−0.0128	0.8274	0.057*
H14B	0.7672	0.1264	0.7875	0.057*
H14C	0.6776	−0.0053	0.7411	0.057*
C15	0.1441 (3)	0.3186 (3)	0.79360 (15)	0.0317 (6)
H15A	0.1087	0.2819	0.8368	0.047*
H15B	0.0709	0.2905	0.7505	0.047*
H15C	0.1532	0.4270	0.7960	0.047*
O1	0.5440 (2)	0.1289 (2)	0.78610 (9)	0.0284 (4)
O2	0.28886 (19)	0.25494 (19)	0.78990 (9)	0.0265 (4)
O3	0.1727 (2)	0.6738 (2)	0.43354 (10)	0.0417 (5)
S1	−0.25196 (7)	0.95280 (7)	0.44816 (4)	0.02811 (19)
Cl1	−0.01562 (8)	0.92675 (7)	0.35926 (3)	0.03212 (19)
Cl2	−0.38786 (8)	0.86816 (11)	0.57543 (4)	0.0513 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0237 (11)	0.0212 (12)	0.0189 (11)	−0.0020 (9)	−0.0004 (9)	−0.0012 (9)
C2	0.0203 (11)	0.0268 (13)	0.0298 (13)	−0.0032 (10)	0.0076 (10)	−0.0045 (10)
C3	0.0309 (13)	0.0281 (13)	0.0250 (13)	−0.0083 (11)	0.0105 (10)	0.0000 (10)
C4	0.0299 (13)	0.0216 (12)	0.0238 (12)	−0.0040 (10)	0.0073 (10)	0.0007 (10)
C5	0.0266 (12)	0.0204 (12)	0.0213 (12)	−0.0007 (9)	0.0050 (10)	−0.0023 (9)
C6	0.0256 (11)	0.0190 (11)	0.0182 (11)	−0.0033 (9)	0.0056 (9)	−0.0021 (9)
C7	0.0264 (12)	0.0298 (14)	0.0260 (13)	−0.0011 (10)	0.0084 (10)	0.0025 (10)
C8	0.0204 (11)	0.0237 (12)	0.0267 (12)	0.0006 (9)	0.0074 (10)	−0.0039 (10)
C9	0.0220 (11)	0.0271 (13)	0.0208 (12)	0.0034 (10)	0.0062 (9)	−0.0009 (10)
C10	0.0195 (11)	0.0242 (12)	0.0211 (12)	0.0005 (9)	0.0025 (9)	−0.0032 (9)
C11	0.0213 (11)	0.0247 (12)	0.0180 (11)	0.0003 (9)	0.0040 (9)	−0.0030 (9)
C12	0.0261 (12)	0.0357 (14)	0.0181 (12)	0.0048 (11)	0.0051 (10)	−0.0003 (10)
C13	0.0265 (12)	0.0410 (15)	0.0232 (13)	0.0034 (11)	0.0077 (10)	−0.0050 (11)
C14	0.0296 (14)	0.0439 (17)	0.0400 (16)	0.0158 (12)	0.0033 (12)	0.0039 (13)
C15	0.0320 (13)	0.0358 (15)	0.0307 (14)	0.0038 (11)	0.0152 (11)	−0.0037 (11)
O1	0.0297 (9)	0.0313 (10)	0.0242 (9)	0.0095 (8)	0.0045 (7)	0.0036 (7)
O2	0.0308 (9)	0.0277 (9)	0.0230 (9)	0.0043 (7)	0.0106 (7)	0.0036 (7)
O3	0.0426 (11)	0.0582 (14)	0.0277 (10)	0.0238 (10)	0.0159 (9)	0.0103 (9)
S1	0.0233 (3)	0.0303 (4)	0.0296 (3)	0.0064 (3)	0.0016 (2)	−0.0019 (3)
Cl1	0.0378 (4)	0.0324 (4)	0.0278 (3)	−0.0019 (3)	0.0102 (3)	0.0059 (3)
Cl2	0.0363 (4)	0.0820 (6)	0.0411 (4)	0.0219 (4)	0.0215 (3)	0.0036 (4)

C1—O1	1.367 (3)	C9—C11	1.491 (3)
C1—C2	1.383 (3)	C10—C11	1.368 (3)
C1—C6	1.415 (3)	C10—Cl1	1.713 (2)
C2—C3	1.404 (4)	C10—S1	1.717 (2)
C2—H2	0.9500	C11—C12	1.430 (3)
C3—C4	1.385 (4)	C12—C13	1.343 (4)
C3—H3	0.9500	C12—H12	0.9500
C4—C5	1.405 (3)	C13—Cl2	1.718 (3)
C4—C7	1.470 (3)	C13—S1	1.720 (3)
C5—C6	1.380 (3)	C14—O1	1.435 (3)
C5—H5	0.9500	C14—H14A	0.9800
C6—O2	1.364 (3)	C14—H14B	0.9800
C7—C8	1.348 (3)	C14—H14C	0.9800
C7—H7	0.9500	C15—O2	1.427 (3)
C8—C9	1.448 (3)	C15—H15A	0.9800
C8—H8	0.9500	C15—H15B	0.9800
C9—O3	1.231 (3)	C15—H15C	0.9800
O1—C1—C2	125.7 (2)	C11—C10—Cl1	129.58 (18)
O1—C1—C6	114.9 (2)	C11—C10—S1	113.31 (18)
C2—C1—C6	119.4 (2)	Cl1—C10—S1	117.10 (14)
C1—C2—C3	119.4 (2)	C10—C11—C12	110.9 (2)
C1—C2—H2	120.3	C10—C11—C9	125.4 (2)
C3—C2—H2	120.3	C12—C11—C9	123.7 (2)
C4—C3—C2	121.5 (2)	C13—C12—C11	112.4 (2)
C4—C3—H3	119.2	C13—C12—H12	123.8
C2—C3—H3	119.2	C11—C12—H12	123.8
C3—C4—C5	118.8 (2)	C12—C13—Cl2	127.1 (2)
C3—C4—C7	119.9 (2)	C12—C13—S1	113.43 (19)
C5—C4—C7	121.3 (2)	Cl2—C13—S1	119.47 (16)
C6—C5—C4	120.3 (2)	O1—C14—H14A	109.5
C6—C5—H5	119.9	O1—C14—H14B	109.5
C4—C5—H5	119.9	H14A—C14—H14B	109.5
O2—C6—C5	124.9 (2)	O1—C14—H14C	109.5
O2—C6—C1	114.6 (2)	H14A—C14—H14C	109.5
C5—C6—C1	120.6 (2)	H14B—C14—H14C	109.5
C8—C7—C4	129.2 (2)	O2—C15—H15A	109.5
C8—C7—H7	115.4	O2—C15—H15B	109.5
C4—C7—H7	115.4	H15A—C15—H15B	109.5
C7—C8—C9	122.1 (2)	O2—C15—H15C	109.5
C7—C8—H8	118.9	H15A—C15—H15C	109.5
C9—C8—H8	118.9	H15B—C15—H15C	109.5
O3—C9—C8	122.1 (2)	C1—O1—C14	116.9 (2)
O3—C9—C11	120.4 (2)	C6—O2—C15	116.97 (19)
C8—C9—C11	117.5 (2)	C10—S1—C13	89.97 (12)
O1—C1—C2—C3	178.3 (2)	S1—C10—C11—C12	0.2 (3)
C6—C1—C2—C3	−0.5 (4)	Cl1—C10—C11—C9	−2.3 (4)
C1—C2—C3—C4	1.3 (4)	S1—C10—C11—C9	179.10 (19)
C2—C3—C4—C5	−0.5 (4)	O3—C9—C11—C10	−12.1 (4)
C2—C3—C4—C7	−177.2 (2)	C8—C9—C11—C10	170.1 (2)
C3—C4—C5—C6	−1.1 (4)	O3—C9—C11—C12	166.6 (3)
C7—C4—C5—C6	175.6 (2)	C8—C9—C11—C12	−11.1 (4)
C4—C5—C6—O2	−177.8 (2)	C10—C11—C12—C13	0.4 (3)
C4—C5—C6—C1	1.9 (4)	C9—C11—C12—C13	−178.6 (2)
O1—C1—C6—O2	−0.3 (3)	C11—C12—C13—Cl2	179.3 (2)
C2—C1—C6—O2	178.7 (2)	C11—C12—C13—S1	−0.8 (3)
O1—C1—C6—C5	179.9 (2)	C2—C1—O1—C14	0.1 (4)
C2—C1—C6—C5	−1.1 (3)	C6—C1—O1—C14	178.9 (2)
C3—C4—C7—C8	−175.4 (3)	C5—C6—O2—C15	1.8 (3)
C5—C4—C7—C8	8.0 (4)	C1—C6—O2—C15	−178.0 (2)
C4—C7—C8—C9	−177.4 (2)	C11—C10—S1—C13	−0.5 (2)
C7—C8—C9—O3	2.2 (4)	Cl1—C10—S1—C13	−179.29 (16)
C7—C8—C9—C11	179.9 (2)	C12—C13—S1—C10	0.7 (2)
Cl1—C10—C11—C12	178.78 (19)	Cl2—C13—S1—C10	−179.34 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3i	0.95	2.53	3.227 (3)	130
C12—H12···O1ii	0.95	2.55	3.441 (3)	157
C14—H14A···O3iii	0.98	2.53	3.474 (3)	161
C15—H15B···Cl1iv	0.98	2.82	3.647 (3)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O3i	0.95	2.53	3.227 (3)	130
C12—H12⋯O1ii	0.95	2.55	3.441 (3)	157
C14—H14A⋯O3iii	0.98	2.53	3.474 (3)	161
C15—H15B⋯Cl1iv	0.98	2.82	3.647 (3)	142

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .