(2E)-1-(5-Chloro-thio-phen-2-yl)-3-(2,4,5-trimeth-oxy-phen-yl)prop-2-en-1-one.

In the title mol-ecule, C(16)H(15)ClO(4)S, the chloro-thio-phene and trimeth-oxy-phenyl rings make a dihedral angle of 31.12 (5)°. The C=C double bond exhibits an E conformation. In the crystal, C-H⋯O inter-actions generate bifurcated bonds, linking the mol-ecules into chains along the b axis.

Related literature

For general background to chalcones, see: Tomazela et al. (2000 ▶); Uchida et al. (1998 ▶); Zyss & Chemla (1987 ▶). For related structures, see: Benmekhbi et al. (2009 ▶).

Experimental

Crystal data

C16H15ClO4S

M = 338.79

Monoclinic,

a = 18.2795 (12) Å

b = 9.0393 (7) Å

c = 9.8673 (6) Å

β = 99.390 (4)°

V = 1608.57 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.38 mm−1

T = 296 K

0.20 × 0.18 × 0.18 mm

Data collection

Bruker SMART APEX CCD detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.928, T max = 0.935

11590 measured reflections

4590 independent reflections

1621 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.197

S = 0.94

4590 reflections

202 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.32 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, 1999 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811028236/pv2418sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028236/pv2418Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811028236/pv2418Isup3.cml

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

C16H15ClO4S	F(000) = 704
Mr = 338.79	Dx = 1.399 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4590 reflections
a = 18.2795 (12) Å	θ = 2.3–30.5°
b = 9.0393 (7) Å	µ = 0.38 mm−1
c = 9.8673 (6) Å	T = 296 K
β = 99.390 (4)°	Block, yellow
V = 1608.57 (19) Å3	0.20 × 0.18 × 0.18 mm
Z = 4

Bruker SMART APEX CCD detector diffractometer	4590 independent reflections
Radiation source: fine-focus sealed tube	1621 reflections with I > 2σ(I)
graphite	Rint = 0.065
ω scans	θmax = 30.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −26→26
Tmin = 0.928, Tmax = 0.935	k = −12→12
11590 measured reflections	l = −13→11

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.197	H-atom parameters constrained
S = 0.94	w = 1/[σ2(Fo2) + (0.0776P)2] where P = (Fo2 + 2Fc2)/3
4590 reflections	(Δ/σ)max = 0.001
202 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.32 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	1.19089 (6)	0.43556 (14)	0.13180 (12)	0.0853 (4)
S1	1.03627 (5)	0.43686 (11)	0.18651 (10)	0.0602 (3)
O1	0.88221 (14)	0.3967 (3)	0.2335 (3)	0.0681 (8)
O2	0.66429 (13)	0.1207 (3)	0.2390 (3)	0.0726 (8)
O3	0.55841 (13)	−0.2151 (3)	−0.1240 (3)	0.0709 (8)
O4	0.66030 (14)	−0.1426 (3)	−0.2658 (3)	0.0810 (9)
C1	1.10339 (19)	0.3619 (4)	0.1052 (4)	0.0596 (10)
C2	1.0792 (2)	0.2480 (5)	0.0231 (4)	0.0704 (12)
H2	1.1088	0.1949	−0.0279	0.085*
C3	1.00321 (19)	0.2181 (4)	0.0233 (4)	0.0547 (9)
H3	0.9770	0.1434	−0.0282	0.066*
C4	0.97267 (17)	0.3111 (4)	0.1075 (3)	0.0489 (9)
C5	0.89668 (19)	0.3155 (4)	0.1409 (4)	0.0553 (10)
C6	0.84197 (18)	0.2173 (4)	0.0627 (4)	0.0539 (9)
H6	0.8521	0.1744	−0.0179	0.065*
C7	0.77806 (18)	0.1879 (4)	0.1045 (4)	0.0537 (9)
H7	0.7700	0.2364	0.1839	0.064*
C8	0.71877 (17)	0.0894 (4)	0.0419 (4)	0.0474 (9)
C9	0.71853 (19)	0.0245 (4)	−0.0852 (4)	0.0520 (9)
H9	0.7561	0.0484	−0.1348	0.062*
C10	0.66447 (19)	−0.0742 (4)	−0.1407 (4)	0.0555 (10)
C11	0.60855 (18)	−0.1124 (4)	−0.0638 (4)	0.0535 (10)
C12	0.60767 (18)	−0.0500 (4)	0.0619 (4)	0.0541 (10)
H12	0.5708	−0.0757	0.1123	0.065*
C13	0.66189 (18)	0.0522 (4)	0.1149 (4)	0.0516 (9)
C14	0.6146 (2)	0.0767 (5)	0.3268 (4)	0.0876 (15)
H14A	0.5646	0.0937	0.2821	0.131*
H14C	0.6240	0.1331	0.4102	0.131*
H14B	0.6213	−0.0266	0.3477	0.131*
C15	0.5106 (2)	−0.2793 (4)	−0.0396 (5)	0.0771 (13)
H15C	0.5398	−0.3263	0.0383	0.116*
H15A	0.4792	−0.3515	−0.0916	0.116*
H15B	0.4805	−0.2034	−0.0084	0.116*
C16	0.7194 (2)	−0.1165 (5)	−0.3418 (4)	0.0914 (16)
H16B	0.7202	−0.0137	−0.3658	0.137*
H16C	0.7118	−0.1753	−0.4239	0.137*
H16A	0.7657	−0.1430	−0.2866	0.137*

	U11	U22	U33	U12	U13	U23
Cl1	0.0596 (6)	0.1155 (10)	0.0833 (9)	−0.0246 (6)	0.0194 (5)	−0.0174 (7)
S1	0.0600 (6)	0.0680 (7)	0.0544 (7)	−0.0145 (5)	0.0151 (4)	−0.0090 (5)
O1	0.0639 (16)	0.083 (2)	0.0595 (19)	−0.0111 (14)	0.0169 (13)	−0.0174 (16)
O2	0.0636 (17)	0.089 (2)	0.074 (2)	−0.0108 (14)	0.0351 (14)	−0.0162 (17)
O3	0.0568 (15)	0.0707 (18)	0.087 (2)	−0.0218 (14)	0.0168 (14)	−0.0001 (15)
O4	0.0796 (19)	0.103 (2)	0.063 (2)	−0.0404 (17)	0.0187 (15)	−0.0202 (17)
C1	0.052 (2)	0.070 (3)	0.057 (3)	−0.008 (2)	0.0081 (17)	0.007 (2)
C2	0.063 (2)	0.079 (3)	0.072 (3)	0.000 (2)	0.019 (2)	−0.017 (2)
C3	0.053 (2)	0.052 (2)	0.059 (3)	−0.0082 (18)	0.0088 (17)	−0.018 (2)
C4	0.051 (2)	0.054 (2)	0.042 (2)	−0.0120 (17)	0.0071 (16)	0.0042 (18)
C5	0.058 (2)	0.060 (2)	0.047 (3)	−0.0123 (19)	0.0077 (17)	0.009 (2)
C6	0.053 (2)	0.064 (2)	0.047 (2)	−0.0090 (18)	0.0144 (17)	−0.0016 (19)
C7	0.055 (2)	0.055 (2)	0.052 (2)	0.0010 (18)	0.0088 (17)	0.0050 (19)
C8	0.0426 (18)	0.048 (2)	0.052 (2)	−0.0011 (16)	0.0083 (16)	0.0051 (18)
C9	0.050 (2)	0.062 (2)	0.046 (2)	−0.0100 (18)	0.0128 (16)	0.0075 (19)
C10	0.054 (2)	0.060 (2)	0.052 (2)	−0.0082 (19)	0.0065 (17)	0.004 (2)
C11	0.0377 (18)	0.052 (2)	0.070 (3)	0.0009 (16)	0.0071 (17)	0.007 (2)
C12	0.0421 (19)	0.056 (2)	0.068 (3)	0.0032 (17)	0.0200 (17)	0.007 (2)
C13	0.0451 (19)	0.055 (2)	0.057 (3)	0.0070 (18)	0.0159 (16)	0.002 (2)
C14	0.073 (3)	0.127 (4)	0.070 (3)	−0.002 (3)	0.032 (2)	0.000 (3)
C15	0.049 (2)	0.065 (3)	0.121 (4)	−0.011 (2)	0.024 (2)	0.010 (3)
C16	0.102 (3)	0.118 (4)	0.062 (3)	−0.052 (3)	0.033 (2)	−0.021 (3)

Cl1—C1	1.713 (4)	C7—C8	1.460 (5)
S1—C1	1.711 (4)	C7—H7	0.9300
S1—C4	1.719 (3)	C8—C9	1.384 (5)
O1—C5	1.234 (4)	C8—C13	1.399 (4)
O2—C13	1.367 (4)	C9—C10	1.377 (5)
O2—C14	1.411 (4)	C9—H9	0.9300
O3—C11	1.370 (4)	C10—C11	1.412 (4)
O3—C15	1.426 (4)	C11—C12	1.365 (5)
O4—C10	1.372 (4)	C12—C13	1.393 (5)
O4—C16	1.430 (4)	C12—H12	0.9300
C1—C2	1.340 (5)	C14—H14A	0.9600
C2—C3	1.415 (5)	C14—H14C	0.9600
C2—H2	0.9300	C14—H14B	0.9600
C3—C4	1.363 (4)	C15—H15C	0.9600
C3—H3	0.9300	C15—H15A	0.9600
C4—C5	1.480 (4)	C15—H15B	0.9600
C5—C6	1.460 (5)	C16—H16B	0.9600
C6—C7	1.327 (4)	C16—H16C	0.9600
C6—H6	0.9300	C16—H16A	0.9600
C1—S1—C4	90.51 (18)	O4—C10—C9	125.5 (3)
C13—O2—C14	119.5 (3)	O4—C10—C11	115.8 (3)
C11—O3—C15	116.9 (3)	C9—C10—C11	118.7 (4)
C10—O4—C16	117.5 (3)	C12—C11—O3	124.6 (3)
C2—C1—S1	113.4 (3)	C12—C11—C10	120.3 (3)
C2—C1—Cl1	126.8 (3)	O3—C11—C10	115.1 (3)
S1—C1—Cl1	119.8 (2)	C11—C12—C13	120.1 (3)
C1—C2—C3	111.9 (3)	C11—C12—H12	119.9
C1—C2—H2	124.0	C13—C12—H12	119.9
C3—C2—H2	124.0	O2—C13—C12	123.6 (3)
C4—C3—C2	112.5 (3)	O2—C13—C8	115.8 (3)
C4—C3—H3	123.7	C12—C13—C8	120.6 (3)
C2—C3—H3	123.7	O2—C14—H14A	109.5
C3—C4—C5	130.2 (3)	O2—C14—H14C	109.5
C3—C4—S1	111.7 (2)	H14A—C14—H14C	109.5
C5—C4—S1	118.1 (3)	O2—C14—H14B	109.5
O1—C5—C6	122.8 (3)	H14A—C14—H14B	109.5
O1—C5—C4	120.2 (3)	H14C—C14—H14B	109.5
C6—C5—C4	116.9 (3)	O3—C15—H15C	109.5
C7—C6—C5	121.3 (3)	O3—C15—H15A	109.5
C7—C6—H6	119.4	H15C—C15—H15A	109.5
C5—C6—H6	119.4	O3—C15—H15B	109.5
C6—C7—C8	128.4 (4)	H15C—C15—H15B	109.5
C6—C7—H7	115.8	H15A—C15—H15B	109.5
C8—C7—H7	115.8	O4—C16—H16B	109.5
C9—C8—C13	118.2 (3)	O4—C16—H16C	109.5
C9—C8—C7	122.3 (3)	H16B—C16—H16C	109.5
C13—C8—C7	119.4 (3)	O4—C16—H16A	109.5
C10—C9—C8	122.1 (3)	H16B—C16—H16A	109.5
C10—C9—H9	119.0	H16C—C16—H16A	109.5
C8—C9—H9	119.0
C4—S1—C1—C2	−0.1 (3)	C16—O4—C10—C9	4.0 (6)
C4—S1—C1—Cl1	179.0 (2)	C16—O4—C10—C11	−174.8 (4)
S1—C1—C2—C3	0.4 (5)	C8—C9—C10—O4	179.8 (3)
Cl1—C1—C2—C3	−178.7 (3)	C8—C9—C10—C11	−1.4 (5)
C1—C2—C3—C4	−0.5 (5)	C15—O3—C11—C12	−11.5 (5)
C2—C3—C4—C5	−177.9 (4)	C15—O3—C11—C10	167.5 (3)
C2—C3—C4—S1	0.4 (4)	O4—C10—C11—C12	−179.8 (3)
C1—S1—C4—C3	−0.2 (3)	C9—C10—C11—C12	1.3 (5)
C1—S1—C4—C5	178.3 (3)	O4—C10—C11—O3	1.1 (5)
C3—C4—C5—O1	170.7 (4)	C9—C10—C11—O3	−177.8 (3)
S1—C4—C5—O1	−7.5 (5)	O3—C11—C12—C13	179.2 (3)
C3—C4—C5—C6	−7.5 (6)	C10—C11—C12—C13	0.2 (5)
S1—C4—C5—C6	174.3 (3)	C14—O2—C13—C12	6.9 (5)
O1—C5—C6—C7	−13.6 (6)	C14—O2—C13—C8	−172.4 (3)
C4—C5—C6—C7	164.6 (3)	C11—C12—C13—O2	179.2 (3)
C5—C6—C7—C8	−177.8 (3)	C11—C12—C13—C8	−1.6 (5)
C6—C7—C8—C9	−8.4 (6)	C9—C8—C13—O2	−179.2 (3)
C6—C7—C8—C13	168.2 (4)	C7—C8—C13—O2	4.0 (5)
C13—C8—C9—C10	0.0 (5)	C9—C8—C13—C12	1.5 (5)
C7—C8—C9—C10	176.6 (3)	C7—C8—C13—C12	−175.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1i	0.93	2.71	3.476 (4)	140
C6—H6···O1i	0.93	2.68	3.597 (5)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1i	0.93	2.71	3.476 (4)	140
C6—H6⋯O1i	0.93	2.68	3.597 (5)	169

Symmetry code: (i) .