(E)-1-(2-Thien-yl)-3-(2,4,5-trimethoxy-phen-yl)prop-2-en-1-one.

In the title mol-ecule, C(16)H(16)O(4)S, the enone fragment, thio-phene ring and benzene ring are individually essentially planar. The thio-phene ring is disordered over two sites, corresponding to a rotation of approximately 180° about the single C-C bond to which it is attached. The approximate ratio of occupancies for the major and minor components is 0.872 (2):0.128 (2). The major component of the thio-phene ring and the benzene ring are twisted from each other by 13.92 (19)°. An intra-molecular C-H⋯O hydrogen bond generates an S(5)S(5) ring motif. The crystal structure is stabilized by inter-molecular C-H⋯O hydrogen-bonding inter-actions. In addition, a π-π stacking inter-action, with a centroid-centroid distance of 3.852 (2) Å, and short S⋯O [2.9378 (12) Å] and O⋯O [2.5811 (16) Å] contacts are observed.

Related literature

For related literature, see: Chantrapromma et al. (2005 ▶, 2006 ▶); Fun et al. (2006 ▶); Patil, Fun et al. (2007 ▶); Patil, Dharmaprakash et al.(2007 ▶). For bond-length data, see: Allen et al. (1987 ▶); Patil et al. (2006 ▶). For graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H16O4S

M = 304.35

Monoclinic,

a = 7.5391 (1) Å

b = 7.9225 (1) Å

c = 24.3399 (3) Å

β = 97.021 (1)°

V = 1442.88 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 100.0 (1) K

0.25 × 0.22 × 0.14 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.942, T max = 0.967

33027 measured reflections

4256 independent reflections

3174 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.120

S = 1.07

4256 reflections

211 parameters

120 restraints

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808021375/lh2658sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021375/lh2658Isup2.hkl

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

C16H16O4S	F000 = 640
Mr = 304.35	Dx = 1.401 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4291 reflections
a = 7.53910 (10) Å	θ = 2.7–28.4º
b = 7.92250 (10) Å	µ = 0.24 mm−1
c = 24.3399 (3) Å	T = 100.0 (1) K
β = 97.0210 (10)º	Block, yellow
V = 1442.88 (3) Å3	0.25 × 0.22 × 0.14 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	4256 independent reflections
Radiation source: fine-focus sealed tube	3174 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.063
T = 100.0(1) K	θmax = 30.1º
φ and ω scans	θmin = 1.7º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −10→10
Tmin = 0.942, Tmax = 0.967	k = −11→10
33027 measured reflections	l = −34→34

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)] = 0.046	H-atom parameters constrained
wR(F2) = 0.120	w = 1/[σ2(Fo2) + (0.0532P)2 + 0.4695P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
4256 reflections	Δρmax = 0.41 e Å−3
211 parameters	Δρmin = −0.22 e Å−3
120 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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	Occ. (<1)
O1	0.21432 (18)	−0.07151 (14)	0.09237 (4)	0.0317 (3)
O2	0.17726 (15)	0.05965 (14)	−0.21790 (4)	0.0241 (2)
O3	0.32216 (15)	−0.21704 (14)	−0.24632 (4)	0.0245 (2)
O4	0.38751 (16)	−0.41134 (14)	−0.05568 (4)	0.0256 (3)
C4	0.1783 (2)	0.22121 (18)	0.08330 (6)	0.0207 (3)
S1	0.17822 (8)	0.24407 (6)	0.153399 (18)	0.02221 (15)	0.870 (2)
C1	0.1475 (5)	0.4570 (4)	0.14728 (11)	0.0232 (6)	0.870 (2)
H1A	0.1413	0.5286	0.1773	0.028*	0.870 (2)
C2	0.1330 (9)	0.5112 (4)	0.09346 (15)	0.0270 (8)	0.870 (2)
H2A	0.1119	0.6223	0.0822	0.032*	0.870 (2)
C3	0.1544 (10)	0.3750 (7)	0.05759 (18)	0.0335 (12)	0.870 (2)
H3A	0.1526	0.3883	0.0196	0.040*	0.870 (2)
S1X	0.1377 (15)	0.3871 (9)	0.0437 (3)	0.0239 (13)	0.130 (2)
C1X	0.145 (7)	0.511 (3)	0.1014 (8)	0.036 (8)*	0.130 (2)
H1XA	0.1481	0.6281	0.1003	0.043*	0.130 (2)
C2X	0.147 (4)	0.421 (2)	0.1494 (9)	0.027 (6)*	0.130 (2)
H2XA	0.1296	0.4635	0.1839	0.032*	0.130 (2)
C3X	0.180 (3)	0.253 (2)	0.1369 (6)	0.0335 (12)	0.130 (2)
H3XA	0.2008	0.1699	0.1640	0.040*	0.130 (2)
C5	0.2048 (2)	0.05105 (19)	0.06134 (6)	0.0227 (3)
C6	0.2186 (2)	0.03664 (19)	0.00174 (6)	0.0237 (3)
H6A	0.1975	0.1315	−0.0206	0.028*
C7	0.2608 (2)	−0.10914 (19)	−0.02109 (6)	0.0224 (3)
H7A	0.2816	−0.2009	0.0027	0.027*
C8	0.2776 (2)	−0.13959 (18)	−0.07931 (6)	0.0203 (3)
C9	0.3410 (2)	−0.29444 (19)	−0.09632 (6)	0.0205 (3)
C10	0.3580 (2)	−0.32485 (19)	−0.15198 (6)	0.0210 (3)
H10A	0.4022	−0.4277	−0.1627	0.025*
C11	0.3088 (2)	−0.20143 (19)	−0.19118 (6)	0.0200 (3)
C12	0.2371 (2)	−0.04789 (19)	−0.17534 (6)	0.0204 (3)
C13	0.2256 (2)	−0.01779 (19)	−0.12019 (6)	0.0211 (3)
H13A	0.1823	0.0857	−0.1097	0.025*
C14	0.0920 (2)	0.2100 (2)	−0.20310 (6)	0.0280 (4)
H14A	0.0559	0.2753	−0.2358	0.042*
H14B	0.1736	0.2746	−0.1780	0.042*
H14C	−0.0113	0.1815	−0.1855	0.042*
C15	0.3832 (2)	−0.3757 (2)	−0.26506 (7)	0.0305 (4)
H15A	0.3869	−0.3710	−0.3043	0.046*
H15B	0.3028	−0.4635	−0.2568	0.046*
H15C	0.5007	−0.3988	−0.2467	0.046*
C16	0.4083 (2)	−0.5814 (2)	−0.07198 (7)	0.0278 (3)
H16B	0.4405	−0.6498	−0.0397	0.042*
H16C	0.5006	−0.5879	−0.0958	0.042*
H16D	0.2979	−0.6215	−0.0914	0.042*

	U11	U22	U33	U12	U13	U23
O1	0.0575 (8)	0.0197 (6)	0.0187 (5)	0.0009 (5)	0.0076 (5)	0.0019 (4)
O2	0.0354 (6)	0.0222 (5)	0.0150 (5)	0.0045 (5)	0.0046 (4)	0.0008 (4)
O3	0.0346 (6)	0.0249 (6)	0.0151 (5)	0.0023 (5)	0.0077 (4)	−0.0036 (4)
O4	0.0389 (6)	0.0205 (5)	0.0167 (5)	0.0049 (5)	0.0009 (4)	−0.0005 (4)
C4	0.0270 (7)	0.0213 (7)	0.0144 (6)	−0.0020 (6)	0.0050 (5)	−0.0017 (5)
S1	0.0312 (3)	0.0219 (2)	0.0139 (2)	−0.00063 (17)	0.0044 (2)	−0.00192 (18)
C1	0.0330 (13)	0.0168 (12)	0.0206 (11)	0.0017 (12)	0.0061 (7)	−0.0042 (9)
C2	0.0443 (19)	0.0168 (11)	0.0206 (11)	−0.0016 (8)	0.0072 (15)	−0.0015 (7)
C3	0.0466 (19)	0.0352 (17)	0.020 (2)	−0.0016 (12)	0.0106 (17)	−0.0004 (13)
S1X	0.041 (3)	0.0111 (18)	0.022 (3)	−0.0021 (16)	0.014 (2)	−0.0060 (17)
C3X	0.0466 (19)	0.0352 (17)	0.020 (2)	−0.0016 (12)	0.0106 (17)	−0.0004 (13)
C5	0.0312 (8)	0.0208 (7)	0.0167 (7)	−0.0011 (6)	0.0048 (6)	−0.0011 (5)
C6	0.0353 (8)	0.0201 (7)	0.0164 (7)	−0.0018 (6)	0.0058 (6)	0.0006 (5)
C7	0.0277 (8)	0.0234 (7)	0.0163 (6)	−0.0010 (6)	0.0025 (6)	−0.0002 (5)
C8	0.0269 (7)	0.0190 (7)	0.0153 (6)	−0.0026 (6)	0.0042 (5)	−0.0023 (5)
C9	0.0242 (7)	0.0203 (7)	0.0166 (7)	−0.0006 (6)	0.0005 (5)	−0.0002 (5)
C10	0.0256 (7)	0.0207 (7)	0.0172 (7)	0.0005 (6)	0.0042 (5)	−0.0033 (5)
C11	0.0228 (7)	0.0234 (7)	0.0140 (6)	−0.0023 (6)	0.0037 (5)	−0.0021 (5)
C12	0.0246 (7)	0.0207 (7)	0.0163 (6)	−0.0017 (6)	0.0039 (5)	0.0006 (5)
C13	0.0286 (8)	0.0184 (7)	0.0169 (7)	−0.0009 (6)	0.0047 (6)	−0.0022 (5)
C14	0.0395 (9)	0.0243 (8)	0.0201 (7)	0.0073 (7)	0.0030 (6)	0.0005 (6)
C15	0.0429 (10)	0.0298 (9)	0.0196 (7)	0.0075 (7)	0.0064 (7)	−0.0071 (6)
C16	0.0396 (9)	0.0207 (7)	0.0221 (7)	0.0019 (7)	−0.0002 (6)	−0.0007 (6)

O1—C5	1.2268 (18)	C3X—H3XA	0.9300
O2—C12	1.3741 (17)	C5—C6	1.472 (2)
O2—C14	1.4206 (19)	C6—C7	1.337 (2)
O3—C11	1.3637 (17)	C6—H6A	0.9300
O3—C15	1.4319 (19)	C7—C8	1.4582 (19)
O4—C9	1.3692 (17)	C7—H7A	0.9300
O4—C16	1.4182 (18)	C8—C9	1.398 (2)
C4—C3X	1.328 (13)	C8—C13	1.407 (2)
C4—C3	1.371 (5)	C9—C10	1.3972 (19)
C4—C5	1.473 (2)	C10—C11	1.385 (2)
C4—S1X	1.636 (7)	C10—H10A	0.9300
C4—S1	1.7158 (15)	C11—C12	1.404 (2)
S1—C1	1.707 (3)	C12—C13	1.376 (2)
C1—C2	1.370 (4)	C13—H13A	0.9300
C1—H1A	0.9300	C14—H14A	0.9600
C2—C3	1.410 (6)	C14—H14B	0.9600
C2—H2A	0.9300	C14—H14C	0.9600
C3—H3A	0.9300	C15—H15A	0.9600
S1X—C1X	1.708 (18)	C15—H15B	0.9600
C1X—C2X	1.368 (17)	C15—H15C	0.9600
C1X—H1XA	0.9300	C16—H16B	0.9600
C2X—C3X	1.391 (17)	C16—H16C	0.9600
C2X—H2XA	0.9300	C16—H16D	0.9600
C12—O2—C14	116.47 (11)	C6—C7—H7A	116.6
C11—O3—C15	117.29 (12)	C8—C7—H7A	116.6
C9—O4—C16	117.89 (11)	C9—C8—C13	117.93 (13)
C3X—C4—C3	105.4 (8)	C9—C8—C7	120.43 (13)
C3X—C4—C5	123.0 (8)	C13—C8—C7	121.61 (13)
C3—C4—C5	131.6 (2)	O4—C9—C10	122.55 (13)
C3X—C4—S1X	113.9 (8)	O4—C9—C8	116.52 (12)
C5—C4—S1X	123.0 (3)	C10—C9—C8	120.92 (13)
C3—C4—S1	110.1 (2)	C11—C10—C9	119.84 (14)
C5—C4—S1	118.30 (11)	C11—C10—H10A	120.1
S1X—C4—S1	118.6 (3)	C9—C10—H10A	120.1
C1—S1—C4	91.96 (10)	O3—C11—C10	124.62 (13)
C2—C1—S1	112.8 (2)	O3—C11—C12	115.23 (13)
C2—C1—H1A	123.6	C10—C11—C12	120.15 (13)
S1—C1—H1A	123.6	O2—C12—C13	125.01 (13)
C1—C2—C3	110.5 (3)	O2—C12—C11	115.59 (12)
C1—C2—H2A	124.7	C13—C12—C11	119.36 (13)
C3—C2—H2A	124.7	C12—C13—C8	121.70 (14)
C4—C3—C2	114.6 (3)	C12—C13—H13A	119.2
C4—C3—H3A	122.7	C8—C13—H13A	119.2
C2—C3—H3A	122.7	O2—C14—H14A	109.5
C4—S1X—C1X	89.5 (9)	O2—C14—H14B	109.5
C2X—C1X—S1X	113.4 (16)	H14A—C14—H14B	109.5
C2X—C1X—H1XA	123.3	O2—C14—H14C	109.5
S1X—C1X—H1XA	123.3	H14A—C14—H14C	109.5
C1X—C2X—C3X	107.3 (17)	H14B—C14—H14C	109.5
C1X—C2X—H2XA	126.4	O3—C15—H15A	109.5
C3X—C2X—H2XA	126.4	O3—C15—H15B	109.5
C4—C3X—C2X	114.5 (14)	H15A—C15—H15B	109.5
C4—C3X—H3XA	122.8	O3—C15—H15C	109.5
C2X—C3X—H3XA	122.8	H15A—C15—H15C	109.5
O1—C5—C6	122.66 (14)	H15B—C15—H15C	109.5
O1—C5—C4	120.09 (13)	O4—C16—H16B	109.5
C6—C5—C4	117.25 (13)	O4—C16—H16C	109.5
C7—C6—C5	121.74 (14)	H16B—C16—H16C	109.5
C7—C6—H6A	119.1	O4—C16—H16D	109.5
C5—C6—H6A	119.1	H16B—C16—H16D	109.5
C6—C7—C8	126.89 (14)	H16C—C16—H16D	109.5
C3X—C4—S1—C1	13 (12)	S1—C4—C5—C6	−175.26 (11)
C3—C4—S1—C1	−0.2 (4)	O1—C5—C6—C7	−7.0 (3)
C5—C4—S1—C1	178.97 (18)	C4—C5—C6—C7	173.08 (15)
S1X—C4—S1—C1	−4.5 (5)	C5—C6—C7—C8	179.63 (14)
C4—S1—C1—C2	1.5 (4)	C6—C7—C8—C9	173.21 (16)
S1—C1—C2—C3	−2.2 (7)	C6—C7—C8—C13	−8.9 (3)
C3X—C4—C3—C2	−2.2 (11)	C16—O4—C9—C10	−16.9 (2)
C5—C4—C3—C2	179.9 (4)	C16—O4—C9—C8	164.24 (14)
S1X—C4—C3—C2	155 (5)	C13—C8—C9—O4	−178.88 (13)
S1—C4—C3—C2	−1.0 (7)	C7—C8—C9—O4	−0.9 (2)
C1—C2—C3—C4	2.1 (8)	C13—C8—C9—C10	2.2 (2)
C3X—C4—S1X—C1X	6(2)	C7—C8—C9—C10	−179.86 (14)
C3—C4—S1X—C1X	−18 (4)	O4—C9—C10—C11	−179.94 (14)
C5—C4—S1X—C1X	−175.8 (18)	C8—C9—C10—C11	−1.1 (2)
S1—C4—S1X—C1X	7.8 (19)	C15—O3—C11—C10	3.3 (2)
C4—S1X—C1X—C2X	−11 (4)	C15—O3—C11—C12	−175.89 (14)
S1X—C1X—C2X—C3X	12 (5)	C9—C10—C11—O3	179.05 (13)
C3—C4—C3X—C2X	4(2)	C9—C10—C11—C12	−1.8 (2)
C5—C4—C3X—C2X	−178.2 (17)	C14—O2—C12—C13	−2.3 (2)
S1X—C4—C3X—C2X	0(3)	C14—O2—C12—C11	175.38 (14)
S1—C4—C3X—C2X	−163 (13)	O3—C11—C12—O2	4.99 (19)
C1X—C2X—C3X—C4	−8(4)	C10—C11—C12—O2	−174.20 (13)
C3X—C4—C5—O1	6.3 (12)	O3—C11—C12—C13	−177.23 (13)
C3—C4—C5—O1	−176.2 (4)	C10—C11—C12—C13	3.6 (2)
S1X—C4—C5—O1	−171.6 (5)	O2—C12—C13—C8	175.11 (14)
S1—C4—C5—O1	4.8 (2)	C11—C12—C13—C8	−2.4 (2)
C3X—C4—C5—C6	−173.8 (12)	C9—C8—C13—C12	−0.4 (2)
C3—C4—C5—C6	3.7 (5)	C7—C8—C13—C12	−178.33 (14)
S1X—C4—C5—C6	8.3 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1i	0.93	2.55	3.363 (4)	146
C7—H7A···O1	0.93	2.52	2.8416 (18)	101
C7—H7A···O4	0.93	2.39	2.7477 (19)	103
C16—H16B···O4ii	0.96	2.56	3.2952 (19)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O1i	0.93	2.55	3.363 (4)	146
C7—H7A⋯O1	0.93	2.52	2.8416 (18)	101
C7—H7A⋯O4	0.93	2.39	2.7477 (19)	103
C16—H16B⋯O4ii	0.96	2.56	3.2952 (19)	133

Symmetry codes: (i) ; (ii) .