1-(2-Hydr-oxy-5-methyl-phen-yl)-3-(3-methylthiophen-2-yl)prop-2-en-1-one.

In the structure of the title compound, C(15)H(14)O(2)S, the benzene ring is nearly coplanar with the thio-phene ring. The hydroxy group substituted at C2 position is in an antiperi-planar conformation with respect to the phenyl ring. The crystal structure exhibits weak intramolecular O-H⋯O hydrogen bonding.

Related literature

For the bioactivity of related compounds, see: Ratty (1988 ▶); Sato et al. (1996 ▶); Tencate et al. (1973 ▶); Murakami et al. (1992 ▶); Gerdin & Srensso (1983 ▶); Shahidi et al.(1988 ▶); Jayashree et al. (2008 ▶); Nijveldt et al. (2001 ▶); Varma & Kinoshita (1976 ▶). For related structures, see: Jasinski et al. (2009 ▶, 2010 ▶).

Experimental

Crystal data

C15H14O2S

M = 258.33

Orthorhombic,

a = 13.6680 (12) Å

b = 13.3750 (8) Å

c = 14.5410 (14) Å

V = 2658.2 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.23 mm−1

T = 293 K

0.27 × 0.25 × 0.23 mm

Data collection

MacScience DIPLabo 32001 diffractometer

4360 measured reflections

2335 independent reflections

1742 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.182

S = 1.07

2335 reflections

166 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.35 e Å−3

Data collection: XPRESS (MacScience, 2002 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810017058/jh2143sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017058/jh2143Isup2.hkl

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

C15H14O2S	F(000) = 1088
Mr = 258.33	Dx = 1.291 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4360 reflections
a = 13.6680 (12) Å	θ = 3.2–25.0°
b = 13.3750 (8) Å	µ = 0.23 mm−1
c = 14.5410 (14) Å	T = 293 K
V = 2658.2 (4) Å3	Rectangular, orange
Z = 8	0.27 × 0.25 × 0.23 mm

MacScience DIPLabo 32001 diffractometer	1742 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.016
graphite	θmax = 25.0°, θmin = 3.2°
Detector resolution: 10.0 pixels mm-1	h = −15→16
ω scans	k = −15→15
4360 measured reflections	l = −17→17
2335 independent reflections

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)] = 0.058	H-atom parameters constrained
wR(F2) = 0.182	w = 1/[σ2(Fo2) + (0.1131P)2 + 0.2932P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2335 reflections	Δρmax = 0.24 e Å−3
166 parameters	Δρmin = −0.35 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: 0.009975

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
S14	0.03308 (6)	0.63213 (6)	0.34076 (5)	0.0917 (3)
O1	−0.30633 (16)	0.21283 (14)	0.47357 (17)	0.1086 (9)
O10	−0.14602 (14)	0.28250 (13)	0.41732 (14)	0.0902 (7)
C2	−0.32536 (19)	0.3053 (2)	0.5061 (2)	0.0824 (9)
C3	−0.4133 (2)	0.3227 (3)	0.5511 (2)	0.0998 (11)
C4	−0.4358 (2)	0.4136 (3)	0.5850 (2)	0.0968 (13)
C5	−0.37207 (18)	0.4947 (2)	0.57621 (16)	0.0817 (9)
C6	−0.28521 (17)	0.47858 (19)	0.53026 (16)	0.0714 (8)
C7	−0.25907 (16)	0.38552 (17)	0.49421 (16)	0.0681 (8)
C8	−0.3971 (2)	0.5955 (3)	0.6154 (2)	0.1067 (14)
C9	−0.16789 (18)	0.36901 (17)	0.44277 (16)	0.0692 (8)
C11	−0.10438 (16)	0.45228 (18)	0.41721 (15)	0.0685 (8)
C12	−0.02561 (16)	0.43481 (19)	0.36459 (17)	0.0702 (8)
C13	0.04379 (16)	0.5047 (2)	0.32810 (16)	0.0724 (8)
C15	0.1358 (3)	0.6508 (3)	0.2772 (2)	0.1040 (12)
C16	0.1769 (2)	0.5658 (3)	0.2486 (2)	0.0996 (13)
C17	0.12548 (19)	0.4798 (2)	0.27636 (17)	0.0830 (9)
C18	0.1554 (2)	0.3751 (3)	0.2526 (2)	0.1080 (14)
H1	−0.25310	0.21280	0.44750	0.1630*
H3	−0.45760	0.27050	0.55800	0.1200*
H4	−0.49520	0.42260	0.61500	0.1160*
H6	−0.24220	0.53190	0.52300	0.0860*
H8A	−0.35680	0.64560	0.58720	0.1600*
H8B	−0.38590	0.59510	0.68060	0.1600*
H8C	−0.46470	0.61010	0.60350	0.1600*
H11	−0.11840	0.51680	0.43720	0.0820*
H12	−0.01450	0.36810	0.34970	0.0840*
H15	0.16080	0.71380	0.26380	0.1250*
H16	0.23380	0.56360	0.21360	0.1200*
H18A	0.14980	0.33340	0.30610	0.1620*
H18B	0.22200	0.37500	0.23160	0.1620*
H18C	0.11370	0.34980	0.20490	0.1620*

	U11	U22	U33	U12	U13	U23
S14	0.1046 (6)	0.0844 (6)	0.0861 (6)	−0.0070 (3)	0.0065 (4)	0.0020 (3)
O1	0.0995 (14)	0.0704 (12)	0.156 (2)	−0.0136 (9)	−0.0070 (13)	0.0142 (12)
O10	0.0902 (12)	0.0694 (11)	0.1110 (14)	0.0007 (9)	0.0016 (10)	−0.0092 (9)
C2	0.0757 (14)	0.0763 (16)	0.0953 (18)	−0.0082 (12)	−0.0099 (13)	0.0177 (14)
C3	0.0765 (17)	0.104 (2)	0.119 (2)	−0.0175 (16)	−0.0017 (16)	0.0356 (19)
C4	0.0715 (16)	0.125 (3)	0.094 (2)	−0.0003 (16)	0.0098 (14)	0.0259 (19)
C5	0.0724 (14)	0.106 (2)	0.0666 (14)	0.0062 (13)	0.0035 (11)	0.0083 (13)
C6	0.0704 (13)	0.0763 (15)	0.0676 (13)	−0.0012 (11)	−0.0008 (10)	0.0029 (11)
C7	0.0659 (13)	0.0703 (14)	0.0681 (13)	−0.0029 (10)	−0.0056 (10)	0.0109 (11)
C8	0.103 (2)	0.124 (3)	0.093 (2)	0.0186 (18)	0.0217 (17)	−0.0114 (19)
C9	0.0698 (13)	0.0652 (14)	0.0725 (14)	0.0004 (10)	−0.0066 (11)	0.0009 (11)
C11	0.0684 (13)	0.0682 (14)	0.0688 (13)	−0.0007 (10)	0.0007 (10)	−0.0006 (11)
C12	0.0714 (14)	0.0743 (15)	0.0650 (13)	0.0034 (10)	−0.0034 (11)	0.0013 (11)
C13	0.0704 (13)	0.0843 (17)	0.0624 (13)	0.0039 (11)	−0.0001 (10)	0.0043 (11)
C15	0.110 (2)	0.112 (2)	0.090 (2)	−0.0278 (19)	0.0034 (17)	0.0192 (18)
C16	0.0887 (19)	0.130 (3)	0.0801 (17)	−0.0134 (18)	0.0133 (14)	0.0117 (17)
C17	0.0744 (14)	0.106 (2)	0.0685 (14)	0.0040 (13)	0.0009 (11)	0.0094 (14)
C18	0.093 (2)	0.125 (3)	0.106 (2)	0.0234 (18)	0.0195 (18)	0.0011 (19)

S14—C13	1.721 (3)	C15—C16	1.335 (5)
S14—C15	1.699 (4)	C16—C17	1.407 (5)
O1—C2	1.350 (3)	C17—C18	1.499 (5)
O10—C9	1.251 (3)	C3—H3	0.9300
O1—H1	0.8200	C4—H4	0.9300
C2—C7	1.415 (3)	C6—H6	0.9300
C2—C3	1.388 (4)	C8—H8A	0.9600
C3—C4	1.348 (5)	C8—H8B	0.9600
C4—C5	1.397 (4)	C8—H8C	0.9600
C5—C6	1.379 (3)	C11—H11	0.9300
C5—C8	1.503 (5)	C12—H12	0.9300
C6—C7	1.397 (3)	C15—H15	0.9300
C7—C9	1.470 (3)	C16—H16	0.9300
C9—C11	1.460 (3)	C18—H18A	0.9600
C11—C12	1.341 (3)	C18—H18B	0.9600
C12—C13	1.434 (3)	C18—H18C	0.9600
C13—C17	1.387 (3)
C13—S14—C15	90.98 (16)	C2—C3—H3	119.00
C2—O1—H1	109.00	C4—C3—H3	119.00
O1—C2—C7	121.9 (2)	C3—C4—H4	119.00
C3—C2—C7	119.0 (3)	C5—C4—H4	119.00
O1—C2—C3	119.1 (3)	C5—C6—H6	119.00
C2—C3—C4	121.4 (3)	C7—C6—H6	119.00
C3—C4—C5	121.7 (3)	C5—C8—H8A	109.00
C4—C5—C6	117.4 (3)	C5—C8—H8B	109.00
C4—C5—C8	121.3 (2)	C5—C8—H8C	109.00
C6—C5—C8	121.3 (2)	H8A—C8—H8B	110.00
C5—C6—C7	122.8 (2)	H8A—C8—H8C	109.00
C2—C7—C6	117.8 (2)	H8B—C8—H8C	109.00
C6—C7—C9	122.8 (2)	C9—C11—H11	120.00
C2—C7—C9	119.4 (2)	C12—C11—H11	120.00
O10—C9—C11	119.2 (2)	C11—C12—H12	116.00
C7—C9—C11	121.3 (2)	C13—C12—H12	116.00
O10—C9—C7	119.5 (2)	S14—C15—H15	123.00
C9—C11—C12	119.3 (2)	C16—C15—H15	124.00
C11—C12—C13	129.0 (2)	C15—C16—H16	123.00
S14—C13—C12	123.37 (18)	C17—C16—H16	123.00
C12—C13—C17	125.2 (2)	C17—C18—H18A	110.00
S14—C13—C17	111.37 (19)	C17—C18—H18B	109.00
S14—C15—C16	113.1 (3)	C17—C18—H18C	110.00
C15—C16—C17	113.4 (3)	H18A—C18—H18B	109.00
C13—C17—C18	124.7 (2)	H18A—C18—H18C	109.00
C16—C17—C18	124.1 (2)	H18B—C18—H18C	109.00
C13—C17—C16	111.2 (2)
C15—S14—C13—C12	−177.8 (2)	C2—C7—C9—C11	170.9 (2)
C15—S14—C13—C17	0.4 (2)	C6—C7—C9—C11	−7.2 (4)
C13—S14—C15—C16	−0.7 (3)	C2—C7—C9—O10	−6.3 (4)
O1—C2—C7—C6	180.0 (2)	C6—C7—C9—O10	175.6 (2)
C3—C2—C7—C6	1.1 (4)	O10—C9—C11—C12	2.1 (3)
C3—C2—C7—C9	−177.1 (2)	C7—C9—C11—C12	−175.2 (2)
O1—C2—C7—C9	1.8 (4)	C9—C11—C12—C13	177.0 (2)
O1—C2—C3—C4	179.9 (3)	C11—C12—C13—S14	−4.3 (4)
C7—C2—C3—C4	−1.3 (4)	C11—C12—C13—C17	177.8 (2)
C2—C3—C4—C5	0.3 (5)	S14—C13—C17—C16	0.0 (3)
C3—C4—C5—C8	−179.1 (3)	C12—C13—C17—C16	178.1 (2)
C3—C4—C5—C6	0.8 (4)	C12—C13—C17—C18	−1.7 (4)
C8—C5—C6—C7	179.0 (2)	S14—C13—C17—C18	−179.8 (2)
C4—C5—C6—C7	−0.9 (4)	S14—C15—C16—C17	0.8 (4)
C5—C6—C7—C2	−0.1 (4)	C15—C16—C17—C13	−0.5 (4)
C5—C6—C7—C9	178.1 (2)	C15—C16—C17—C18	179.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O10	0.82	1.79	2.518 (3)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O10	0.82	1.79	2.518 (3)	147