4-Hy-droxy-6-methyl-3-[3-(thio-phen-2-yl)acrylo-yl]-2H-pyran-2-one.

The title compound, C13H10O4S, crystallizes with two mol-ecules in the asymmetric unit in which the rings make dihedral angles of 3.9 (1) and 6.0 (1)°; this planarity is due in part to the presence of an intra-molecular O-H⋯O hydrogen bond, which generates an S(6) ring in each mol-ecule. Both mol-ecules represent E isomers with respect to the central C=C bond. In the crystal, mol-ecules are linked by C-H⋯O inter-actions into a three-dimensional network.

Related literature

For pharmacological properties of chalcones, see: Wattenberg et al. (1994 ▶); Dinkova-Kostova et al. (1998 ▶); Ram et al. (2000 ▶); Kidwai et al. (2001 ▶); Ballesteros et al. (1995 ▶). For their non-linear optical properties, see: Fichou et al. (1988 ▶) and for their importance, see: Tomazela et al. (2000 ▶). For precursors in the synthesis of flavonoids, see: Drexler & Amiridis (2003 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C13H10O4S

M = 262.27

Triclinic,

a = 8.0737 (4) Å

b = 9.9428 (5) Å

c = 15.0887 (8) Å

α = 87.770 (1)°

β = 87.779 (3)°

γ = 80.678 (4)°

V = 1193.70 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 293 K

0.5 × 0.4 × 0.2 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.875, T max = 0.947

25106 measured reflections

6954 independent reflections

5295 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.157

S = 1.06

6954 reflections

326 parameters

H-atom parameters constrained

Δρmax = 0.97 e Å−3

Δρmin = −0.30 e Å−3

Data collection: COLLECT (Nonius, 2002 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: EVALCCD (Duisenberg et al., 2003 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PARST (Nardelli, 1995 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813003826/ld2095sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813003826/ld2095Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813003826/ld2095Isup3.cml

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

C13H10O4S	Z = 4
Mr = 262.27	F(000) = 544
Triclinic, P1	Dx = 1.459 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0737 (4) Å	Cell parameters from 102968 reflections
b = 9.9428 (5) Å	θ = 2.9–27.5°
c = 15.0887 (8) Å	µ = 0.27 mm−1
α = 87.770 (1)°	T = 293 K
β = 87.779 (3)°	Block, brown
γ = 80.678 (4)°	0.5 × 0.4 × 0.2 mm
V = 1193.70 (11) Å3

Nonius KappaCCD diffractometer	6954 independent reflections
Radiation source: Enraf Nonius FR590	5295 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
Detector resolution: 9 pixels mm-1	θmax = 30.0°, θmin = 2.1°
CCD rotation images, thin slices scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	k = −13→13
Tmin = 0.875, Tmax = 0.947	l = −21→21
25106 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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0755P)2 + 0.747P] where P = (Fo2 + 2Fc2)/3
6954 reflections	(Δ/σ)max = 0.001
326 parameters	Δρmax = 0.97 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

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.

	x	y	z	Uiso*/Ueq
S2	0.46904 (7)	0.30887 (5)	0.54080 (4)	0.03338 (14)
S1	0.88623 (7)	0.31448 (5)	0.04850 (4)	0.03337 (14)
O2	0.57005 (19)	−0.13416 (14)	−0.19215 (9)	0.0300 (3)
O4	0.7556 (2)	−0.19703 (16)	0.10407 (10)	0.0363 (3)
O3	0.6293 (2)	−0.36848 (16)	0.03371 (11)	0.0417 (4)
H33	0.6698	−0.3296	0.0725	0.063*
O5	0.99995 (19)	−0.14198 (15)	0.30123 (10)	0.0311 (3)
O8	0.8369 (2)	−0.18574 (16)	0.60568 (10)	0.0351 (3)
O7	1.0375 (2)	−0.35666 (17)	0.53507 (11)	0.0423 (4)
H77	0.9792	−0.3154	0.5741	0.063*
O6	0.8273 (2)	0.03013 (16)	0.35590 (11)	0.0415 (4)
O1	0.6537 (2)	0.04135 (16)	−0.13444 (11)	0.0400 (4)
C17	0.9154 (2)	−0.15767 (19)	0.45626 (13)	0.0247 (4)
C4	0.6592 (2)	−0.15850 (18)	−0.04027 (12)	0.0237 (4)
C1	0.5297 (3)	−0.2617 (2)	−0.18823 (14)	0.0301 (4)
C5	0.6115 (3)	−0.2898 (2)	−0.03754 (14)	0.0281 (4)
C2	0.5453 (3)	−0.3400 (2)	−0.11347 (15)	0.0324 (4)
H2	0.5133	−0.4258	−0.1114	0.039*
C9	0.9119 (3)	0.1816 (2)	0.12658 (13)	0.0296 (4)
C3	0.6316 (2)	−0.0752 (2)	−0.12040 (13)	0.0263 (4)
C22	0.5087 (3)	0.1834 (2)	0.62381 (13)	0.0277 (4)
C14	1.0980 (3)	−0.2661 (2)	0.30732 (14)	0.0300 (4)
C25	0.3326 (3)	0.4103 (2)	0.60884 (17)	0.0385 (5)
H25	0.275	0.4954	0.5916	0.046*
C19	0.8208 (2)	−0.1100 (2)	0.53485 (13)	0.0269 (4)
C18	0.9056 (3)	−0.0812 (2)	0.37306 (13)	0.0275 (4)
C16	1.0214 (3)	−0.2859 (2)	0.46114 (14)	0.0291 (4)
C10	0.9849 (3)	0.2172 (2)	0.20074 (14)	0.0346 (5)
H10	1.0118	0.1582	0.2493	0.042*
C6	0.7344 (2)	−0.1158 (2)	0.03667 (13)	0.0269 (4)
C21	0.6233 (3)	0.0584 (2)	0.61300 (14)	0.0291 (4)
H21	0.6401	−0.0005	0.6624	0.035*
C23	0.4178 (3)	0.2221 (2)	0.69960 (14)	0.0325 (4)
H23	0.4214	0.1682	0.7515	0.039*
C20	0.7082 (2)	0.0192 (2)	0.53790 (13)	0.0281 (4)
H20	0.6947	0.0754	0.4871	0.034*
C15	1.1117 (3)	−0.3389 (2)	0.38406 (15)	0.0321 (4)
H15	1.18	−0.4237	0.3869	0.038*
C7	0.7857 (3)	0.0168 (2)	0.04186 (14)	0.0307 (4)
H7	0.77	0.0782	−0.0063	0.037*
C13	0.4714 (3)	−0.2980 (3)	−0.27485 (17)	0.0445 (6)
H13A	0.4448	−0.3887	−0.2704	0.067*
H13B	0.5586	−0.2938	−0.3195	0.067*
H13C	0.3732	−0.2349	−0.2907	0.067*
C24	0.3181 (3)	0.3516 (2)	0.69120 (16)	0.0374 (5)
H24	0.25	0.3927	0.7369	0.045*
C12	0.9682 (3)	0.4177 (2)	0.11694 (16)	0.0383 (5)
H12	0.9796	0.5076	0.1023	0.046*
C26	1.1800 (3)	−0.3059 (3)	0.22020 (16)	0.0414 (5)
H26A	1.2477	−0.3943	0.2264	0.062*
H26B	1.2496	−0.2403	0.2004	0.062*
H26C	1.0955	−0.3088	0.1776	0.062*
C11	1.0149 (3)	0.3533 (2)	0.19538 (15)	0.0377 (5)
H11	1.0615	0.3944	0.2405	0.045*
C8	0.8554 (3)	0.0524 (2)	0.11472 (14)	0.0318 (4)
H8	0.8688	−0.0112	0.1618	0.038*

	U11	U22	U33	U12	U13	U23
S2	0.0367 (3)	0.0325 (3)	0.0306 (3)	−0.0057 (2)	−0.0036 (2)	0.0072 (2)
S1	0.0414 (3)	0.0313 (3)	0.0277 (3)	−0.0072 (2)	−0.0059 (2)	0.00652 (19)
O2	0.0375 (8)	0.0285 (7)	0.0251 (7)	−0.0092 (6)	−0.0039 (6)	0.0036 (5)
O4	0.0454 (9)	0.0397 (8)	0.0232 (7)	−0.0067 (7)	−0.0021 (6)	0.0069 (6)
O3	0.0556 (10)	0.0352 (8)	0.0370 (9)	−0.0179 (7)	−0.0078 (7)	0.0151 (7)
O5	0.0372 (8)	0.0296 (7)	0.0260 (7)	−0.0057 (6)	0.0022 (6)	0.0035 (6)
O8	0.0415 (9)	0.0384 (8)	0.0233 (7)	−0.0013 (7)	−0.0040 (6)	0.0069 (6)
O7	0.0514 (10)	0.0375 (8)	0.0315 (8)	0.0106 (7)	−0.0033 (7)	0.0088 (6)
O6	0.0513 (10)	0.0331 (8)	0.0341 (8)	0.0057 (7)	0.0066 (7)	0.0135 (6)
O1	0.0604 (11)	0.0289 (7)	0.0338 (8)	−0.0165 (7)	−0.0139 (7)	0.0116 (6)
C17	0.0250 (9)	0.0250 (8)	0.0243 (9)	−0.0052 (7)	−0.0034 (7)	0.0028 (7)
C4	0.0244 (9)	0.0227 (8)	0.0235 (9)	−0.0036 (6)	0.0014 (7)	0.0035 (7)
C1	0.0271 (9)	0.0295 (9)	0.0345 (11)	−0.0064 (8)	−0.0013 (8)	−0.0029 (8)
C5	0.0283 (9)	0.0257 (9)	0.0301 (10)	−0.0057 (7)	0.0017 (7)	0.0060 (7)
C2	0.0319 (10)	0.0256 (9)	0.0407 (12)	−0.0084 (8)	−0.0013 (8)	0.0013 (8)
C9	0.0350 (10)	0.0291 (9)	0.0247 (9)	−0.0054 (8)	−0.0039 (8)	0.0043 (7)
C3	0.0277 (9)	0.0269 (9)	0.0243 (9)	−0.0048 (7)	−0.0020 (7)	0.0033 (7)
C22	0.0283 (9)	0.0285 (9)	0.0267 (9)	−0.0068 (7)	−0.0028 (7)	0.0037 (7)
C14	0.0300 (10)	0.0272 (9)	0.0349 (11)	−0.0105 (8)	0.0010 (8)	−0.0028 (8)
C25	0.0370 (12)	0.0305 (10)	0.0457 (13)	0.0024 (9)	−0.0084 (10)	0.0001 (9)
C19	0.0272 (9)	0.0281 (9)	0.0264 (9)	−0.0072 (7)	−0.0043 (7)	0.0017 (7)
C18	0.0287 (9)	0.0271 (9)	0.0268 (9)	−0.0059 (7)	0.0006 (7)	0.0035 (7)
C16	0.0298 (10)	0.0286 (9)	0.0287 (10)	−0.0044 (8)	−0.0058 (8)	0.0044 (8)
C10	0.0419 (12)	0.0382 (11)	0.0255 (10)	−0.0130 (9)	−0.0025 (8)	0.0048 (8)
C6	0.0261 (9)	0.0274 (9)	0.0258 (9)	−0.0003 (7)	0.0011 (7)	0.0009 (7)
C21	0.0301 (10)	0.0296 (9)	0.0279 (10)	−0.0064 (8)	−0.0030 (8)	0.0044 (8)
C23	0.0341 (11)	0.0337 (10)	0.0292 (10)	−0.0050 (8)	−0.0010 (8)	0.0020 (8)
C20	0.0271 (9)	0.0293 (9)	0.0278 (10)	−0.0045 (7)	−0.0031 (7)	0.0040 (7)
C15	0.0309 (10)	0.0272 (9)	0.0372 (11)	−0.0019 (8)	−0.0014 (8)	−0.0007 (8)
C7	0.0330 (10)	0.0292 (9)	0.0293 (10)	−0.0046 (8)	−0.0019 (8)	0.0049 (8)
C13	0.0505 (14)	0.0449 (13)	0.0406 (13)	−0.0123 (11)	−0.0105 (11)	−0.0052 (10)
C24	0.0352 (11)	0.0369 (11)	0.0383 (12)	0.0001 (9)	0.0007 (9)	−0.0060 (9)
C12	0.0479 (13)	0.0301 (10)	0.0389 (12)	−0.0129 (9)	−0.0022 (10)	0.0023 (9)
C26	0.0508 (14)	0.0373 (11)	0.0379 (12)	−0.0143 (10)	0.0099 (10)	−0.0064 (9)
C11	0.0468 (13)	0.0400 (11)	0.0293 (11)	−0.0156 (10)	−0.0020 (9)	−0.0037 (9)
C8	0.0346 (11)	0.0321 (10)	0.0274 (10)	−0.0034 (8)	0.0013 (8)	0.0042 (8)

S2—C25	1.708 (2)	C22—C21	1.435 (3)
S2—C22	1.735 (2)	C14—C15	1.340 (3)
S1—C12	1.707 (2)	C14—C26	1.487 (3)
S1—C9	1.728 (2)	C25—C24	1.361 (3)
O2—C1	1.358 (2)	C25—H25	0.93
O2—C3	1.396 (2)	C19—C20	1.450 (3)
O4—C6	1.273 (2)	C16—C15	1.421 (3)
O3—C5	1.303 (2)	C10—C11	1.412 (3)
O3—H33	0.82	C10—H10	0.93
O5—C14	1.356 (3)	C6—C7	1.450 (3)
O5—C18	1.399 (3)	C21—C20	1.339 (3)
O8—C19	1.281 (2)	C21—H21	0.93
O7—C16	1.295 (2)	C23—C24	1.408 (3)
O7—H77	0.82	C23—H23	0.93
O6—C18	1.206 (2)	C20—H20	0.93
O1—C3	1.210 (2)	C15—H15	0.93
C17—C16	1.417 (3)	C7—C8	1.339 (3)
C17—C19	1.439 (3)	C7—H7	0.93
C17—C18	1.440 (3)	C13—H13A	0.96
C4—C5	1.418 (3)	C13—H13B	0.96
C4—C6	1.440 (3)	C13—H13C	0.96
C4—C3	1.443 (3)	C24—H24	0.93
C1—C2	1.344 (3)	C12—C11	1.360 (3)
C1—C13	1.483 (3)	C12—H12	0.93
C5—C2	1.423 (3)	C26—H26A	0.96
C2—H2	0.93	C26—H26B	0.96
C9—C10	1.369 (3)	C26—H26C	0.96
C9—C8	1.450 (3)	C11—H11	0.93
C22—C23	1.368 (3)	C8—H8	0.93
C25—S2—C22	91.77 (11)	C9—C10—C11	112.55 (19)
C12—S1—C9	91.51 (10)	C9—C10—H10	123.7
C1—O2—C3	123.26 (16)	C11—C10—H10	123.7
C5—O3—H33	109.5	O4—C6—C4	118.89 (18)
C14—O5—C18	123.20 (16)	O4—C6—C7	117.96 (18)
C16—O7—H77	109.5	C4—C6—C7	123.15 (17)
C16—C17—C19	118.31 (17)	C20—C21—C22	125.64 (19)
C16—C17—C18	118.88 (18)	C20—C21—H21	117.2
C19—C17—C18	122.81 (17)	C22—C21—H21	117.2
C5—C4—C6	118.36 (17)	C22—C23—C24	113.3 (2)
C5—C4—C3	118.30 (17)	C22—C23—H23	123.4
C6—C4—C3	123.34 (17)	C24—C23—H23	123.4
C2—C1—O2	121.62 (19)	C21—C20—C19	120.74 (18)
C2—C1—C13	127.2 (2)	C21—C20—H20	119.6
O2—C1—C13	111.21 (19)	C19—C20—H20	119.6
O3—C5—C4	121.18 (18)	C14—C15—C16	119.67 (19)
O3—C5—C2	118.20 (18)	C14—C15—H15	120.2
C4—C5—C2	120.61 (18)	C16—C15—H15	120.2
C1—C2—C5	119.11 (18)	C8—C7—C6	121.25 (19)
C1—C2—H2	120.4	C8—C7—H7	119.4
C5—C2—H2	120.4	C6—C7—H7	119.4
C10—C9—C8	125.57 (19)	C1—C13—H13A	109.5
C10—C9—S1	111.12 (16)	C1—C13—H13B	109.5
C8—C9—S1	123.26 (15)	H13A—C13—H13B	109.5
O1—C3—O2	114.36 (17)	C1—C13—H13C	109.5
O1—C3—C4	128.67 (18)	H13A—C13—H13C	109.5
O2—C3—C4	116.96 (16)	H13B—C13—H13C	109.5
C23—C22—C21	125.88 (19)	C25—C24—C23	112.6 (2)
C23—C22—S2	110.40 (15)	C25—C24—H24	123.7
C21—C22—S2	123.71 (16)	C23—C24—H24	123.7
C15—C14—O5	121.52 (19)	C11—C12—S1	112.14 (17)
C15—C14—C26	127.2 (2)	C11—C12—H12	123.9
O5—C14—C26	111.28 (19)	S1—C12—H12	123.9
C24—C25—S2	111.97 (17)	C14—C26—H26A	109.5
C24—C25—H25	124	C14—C26—H26B	109.5
S2—C25—H25	124	H26A—C26—H26B	109.5
O8—C19—C17	118.31 (18)	C14—C26—H26C	109.5
O8—C19—C20	118.39 (19)	H26A—C26—H26C	109.5
C17—C19—C20	123.31 (17)	H26B—C26—H26C	109.5
O6—C18—O5	114.24 (18)	C12—C11—C10	112.6 (2)
O6—C18—C17	129.1 (2)	C12—C11—H11	123.7
O5—C18—C17	116.70 (17)	C10—C11—H11	123.7
O7—C16—C17	121.05 (19)	C7—C8—C9	125.68 (19)
O7—C16—C15	118.95 (19)	C7—C8—H8	117.2
C17—C16—C15	120.00 (18)	C9—C8—H8	117.2

D—H···A	D—H	H···A	D···A	D—H···A
O3—H33···O4	0.82	1.68	2.421 (2)	150
O7—H77···O8	0.82	1.65	2.400 (2)	150
C8—H8···O5	0.93	2.60	3.481 (3)	159
C10—H10···O6	0.93	2.59	3.280 (3)	132
C10—H10···O8i	0.93	2.59	3.288 (3)	132
C13—H13C···O6ii	0.96	2.58	3.507 (3)	164
C23—H23···O4iii	0.93	2.56	3.245 (3)	131
C25—H25···O7iv	0.93	2.38	3.240 (3)	153
C26—H26B···O1v	0.96	2.41	3.338 (3)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H33⋯O4	0.82	1.68	2.421 (2)	150
O7—H77⋯O8	0.82	1.65	2.400 (2)	150
C8—H8⋯O5	0.93	2.60	3.481 (3)	159
C10—H10⋯O6	0.93	2.59	3.280 (3)	132
C10—H10⋯O8i	0.93	2.59	3.288 (3)	132
C13—H13C⋯O6ii	0.96	2.58	3.507 (3)	164
C23—H23⋯O4iii	0.93	2.56	3.245 (3)	131
C25—H25⋯O7iv	0.93	2.38	3.240 (3)	153
C26—H26B⋯O1v	0.96	2.41	3.338 (3)	163

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