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

The mol-ecule of the title heteroaryl chalcone, C(16)H(16)O(4)S, which consists of substituted thio-phene and benzene rings bridged by the prop-2-en-1-one group, is slightly twisted. The dihedral angle between the thio-phene and 3,4,5-trimethoxy-phenyl rings is 12.18 (4)°. The three meth-oxy groups have two different conformations; two meth-oxy groups are coplanar [C-O-C-C torsion angles = -1.38 (12) and 0.47 (12)°] whereas the third is (-)-synclinal with the benzene ring. In the crystal structure, adjacent mol-ecules are linked in a face-to-side manner into chains along the c axis by weak C-H⋯O(enone) inter-actions. These chains are stacked along the b axis by weak C-H⋯O(meth-oxy) inter-actions.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Chantrapromma et al. (2009 ▶); Patil et al. (2006 ▶; 2007 ▶); Suwunwong et al. (2009a ▶,b ▶). For background to and applications of chalcones, see: Dimmock et al. (1999 ▶); Go et al. (2005 ▶); Jung et al. (2008 ▶); Ni et al. (2004 ▶); Patil et al. (2007 ▶); Patil & Dharmaprakash (2008 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer, (1986 ▶).

Experimental

Crystal data

C16H16O4S

M = 304.36

Orthorhombic,

a = 25.3323 (8) Å

b = 3.9816 (1) Å

c = 14.0163 (4) Å

V = 1413.73 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 100 K

0.58 × 0.31 × 0.21 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.872, T max = 0.951

56940 measured reflections

7416 independent reflections

7177 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.099

S = 1.10

7416 reflections

193 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.66 e Å−3

Δρmin = −0.54 e Å−3

Absolute structure: Flack (1983 ▶), 3588 Friedel pairs

Flack parameter: 0.04 (4)

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; 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, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809021850/sj2627sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809021850/sj2627Isup2.hkl

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

C16H16O4S	Dx = 1.430 Mg m−3
Mr = 304.36	Melting point = 420–421 K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 7416 reflections
a = 25.3323 (8) Å	θ = 2.2–37.5°
b = 3.9816 (1) Å	µ = 0.24 mm−1
c = 14.0163 (4) Å	T = 100 K
V = 1413.73 (7) Å3	Block, pale yellow
Z = 4	0.58 × 0.31 × 0.21 mm
F(000) = 640

Bruker APEXII CCD area-detector diffractometer	7416 independent reflections
Radiation source: sealed tube	7177 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 37.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −43→43
Tmin = 0.872, Tmax = 0.951	k = −6→6
56940 measured reflections	l = −23→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)] = 0.033	H-atom parameters constrained
wR(F2) = 0.099	w = 1/[σ2(Fo2) + (0.0672P)2 + 0.1429P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.001
7416 reflections	Δρmax = 0.66 e Å−3
193 parameters	Δρmin = −0.54 e Å−3
1 restraint	Absolute structure: Flack (1983), 3588 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.04 (4)

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 120.0 (1) K.

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
S1	0.249987 (8)	0.46794 (6)	0.47989 (2)	0.01892 (5)
O1	0.25370 (3)	0.4617 (3)	0.68801 (7)	0.02618 (18)
O2	0.40965 (3)	0.51095 (18)	1.13056 (5)	0.01662 (11)
O3	0.49824 (2)	0.83176 (19)	1.08244 (5)	0.01615 (10)
O4	0.51691 (3)	1.02802 (19)	0.90201 (5)	0.01753 (11)
C1	0.28105 (4)	0.5872 (3)	0.37853 (6)	0.02121 (16)
H1A	0.2679	0.5465	0.3177	0.025*
C2	0.32771 (4)	0.7503 (3)	0.39595 (7)	0.02174 (16)
H2A	0.3493	0.8331	0.3477	0.026*
C3	0.34021 (3)	0.7815 (2)	0.49530 (5)	0.01517 (12)
H3A	0.3702	0.8844	0.5200	0.018*
C4	0.29890 (3)	0.6283 (2)	0.55061 (6)	0.01440 (12)
C5	0.29401 (3)	0.5880 (2)	0.65390 (6)	0.01617 (13)
C6	0.33914 (3)	0.6919 (2)	0.71401 (6)	0.01613 (13)
H6A	0.3662	0.8202	0.6878	0.019*
C7	0.34122 (3)	0.6018 (2)	0.80632 (6)	0.01549 (13)
H7A	0.3122	0.4836	0.8294	0.019*
C8	0.38341 (3)	0.6666 (2)	0.87483 (5)	0.01329 (11)
C9	0.37539 (3)	0.5559 (2)	0.96864 (6)	0.01372 (11)
H9A	0.3441	0.4479	0.9849	0.016*
C10	0.41415 (3)	0.6073 (2)	1.03751 (5)	0.01261 (11)
C11	0.46146 (3)	0.7683 (2)	1.01284 (5)	0.01296 (11)
C12	0.46951 (3)	0.8767 (2)	0.91840 (5)	0.01333 (12)
C13	0.43078 (3)	0.8266 (2)	0.84955 (6)	0.01399 (12)
H13A	0.4362	0.8985	0.7872	0.017*
C14	0.36101 (4)	0.3538 (2)	1.15750 (6)	0.01816 (14)
H14A	0.3619	0.3001	1.2243	0.027*
H14B	0.3563	0.1516	1.1212	0.027*
H14C	0.3322	0.5043	1.1452	0.027*
C15	0.54355 (3)	0.6178 (2)	1.07845 (8)	0.02027 (15)
H15A	0.5681	0.6817	1.1274	0.030*
H15B	0.5601	0.6391	1.0172	0.030*
H15C	0.5329	0.3890	1.0881	0.030*
C16	0.52661 (4)	1.1439 (3)	0.80695 (6)	0.01969 (15)
H16A	0.5598	1.2597	0.8049	0.030*
H16B	0.4989	1.2941	0.7880	0.030*
H16C	0.5276	0.9555	0.7642	0.030*

	U11	U22	U33	U12	U13	U23
S1	0.01673 (9)	0.02390 (10)	0.01613 (9)	−0.00032 (6)	−0.00311 (6)	0.00034 (9)
O1	0.0181 (3)	0.0441 (5)	0.0164 (3)	−0.0106 (3)	−0.0019 (2)	0.0083 (3)
O2	0.0169 (2)	0.0225 (3)	0.0104 (2)	−0.0028 (2)	0.00034 (19)	0.00240 (19)
O3	0.0152 (2)	0.0203 (3)	0.0130 (2)	−0.00066 (19)	−0.00317 (18)	−0.0026 (2)
O4	0.0148 (2)	0.0241 (3)	0.0136 (2)	−0.0053 (2)	0.0005 (2)	0.0021 (2)
C1	0.0243 (4)	0.0266 (4)	0.0127 (3)	0.0053 (3)	−0.0033 (3)	−0.0005 (3)
C2	0.0220 (4)	0.0247 (4)	0.0185 (3)	0.0027 (3)	0.0059 (3)	0.0038 (3)
C3	0.0144 (3)	0.0203 (3)	0.0108 (3)	0.0051 (2)	−0.0017 (2)	−0.0003 (2)
C4	0.0135 (3)	0.0168 (3)	0.0129 (3)	0.0002 (2)	−0.0012 (2)	0.0020 (2)
C5	0.0142 (3)	0.0215 (3)	0.0128 (3)	−0.0013 (3)	−0.0015 (2)	0.0025 (2)
C6	0.0147 (3)	0.0199 (3)	0.0138 (3)	−0.0014 (2)	−0.0017 (2)	0.0012 (2)
C7	0.0134 (3)	0.0206 (3)	0.0125 (3)	−0.0006 (2)	−0.0014 (2)	0.0006 (2)
C8	0.0123 (3)	0.0168 (3)	0.0108 (2)	0.0004 (2)	−0.0006 (2)	−0.0002 (2)
C9	0.0125 (3)	0.0169 (3)	0.0117 (3)	−0.0006 (2)	−0.0001 (2)	0.0002 (2)
C10	0.0128 (3)	0.0149 (3)	0.0101 (3)	0.0006 (2)	0.0003 (2)	0.0001 (2)
C11	0.0130 (3)	0.0153 (3)	0.0105 (2)	−0.0002 (2)	−0.0003 (2)	−0.0003 (2)
C12	0.0127 (3)	0.0157 (3)	0.0116 (3)	−0.0003 (2)	0.0010 (2)	−0.0007 (2)
C13	0.0129 (3)	0.0178 (3)	0.0113 (3)	0.0000 (2)	0.0002 (2)	0.0001 (2)
C14	0.0186 (3)	0.0206 (4)	0.0152 (3)	−0.0016 (3)	0.0039 (2)	0.0030 (3)
C15	0.0174 (3)	0.0188 (3)	0.0246 (4)	0.0001 (3)	−0.0066 (3)	−0.0001 (3)
C16	0.0171 (3)	0.0252 (4)	0.0168 (3)	−0.0013 (3)	0.0032 (3)	0.0051 (3)

S1—C1	1.6921 (11)	C7—C8	1.4598 (11)
S1—C4	1.7104 (8)	C7—H7A	0.9300
O1—C5	1.2347 (11)	C8—C9	1.4015 (11)
O2—C10	1.3642 (10)	C8—C13	1.4040 (11)
O2—C14	1.4325 (11)	C9—C10	1.3920 (11)
O3—C11	1.3725 (10)	C9—H9A	0.9300
O3—C15	1.4304 (12)	C10—C11	1.4023 (11)
O4—C12	1.3630 (10)	C11—C12	1.4073 (11)
O4—C16	1.4312 (11)	C12—C13	1.3905 (11)
C1—C2	1.3704 (15)	C13—H13A	0.9300
C1—H1A	0.9300	C14—H14A	0.9600
C2—C3	1.4335 (13)	C14—H14B	0.9600
C2—H2A	0.9300	C14—H14C	0.9600
C3—C4	1.4382 (12)	C15—H15A	0.9600
C3—H3A	0.9300	C15—H15B	0.9600
C4—C5	1.4619 (12)	C15—H15C	0.9600
C5—C6	1.4792 (12)	C16—H16A	0.9600
C6—C7	1.3437 (11)	C16—H16B	0.9600
C6—H6A	0.9300	C16—H16C	0.9600
C1—S1—C4	92.57 (5)	O2—C10—C9	124.24 (7)
C10—O2—C14	116.54 (7)	O2—C10—C11	115.83 (7)
C11—O3—C15	114.04 (7)	C9—C10—C11	119.93 (7)
C12—O4—C16	116.78 (7)	O3—C11—C10	119.29 (7)
C2—C1—S1	112.61 (7)	O3—C11—C12	120.91 (7)
C2—C1—H1A	123.7	C10—C11—C12	119.73 (7)
S1—C1—H1A	123.7	O4—C12—C13	124.62 (7)
C1—C2—C3	113.88 (8)	O4—C12—C11	114.94 (7)
C1—C2—H2A	123.1	C13—C12—C11	120.43 (7)
C3—C2—H2A	123.1	C12—C13—C8	119.54 (7)
C2—C3—C4	109.02 (8)	C12—C13—H13A	120.2
C2—C3—H3A	125.5	C8—C13—H13A	120.2
C4—C3—H3A	125.5	O2—C14—H14A	109.5
C3—C4—C5	129.94 (7)	O2—C14—H14B	109.5
C3—C4—S1	111.91 (6)	H14A—C14—H14B	109.5
C5—C4—S1	118.14 (6)	O2—C14—H14C	109.5
O1—C5—C4	119.89 (8)	H14A—C14—H14C	109.5
O1—C5—C6	122.19 (8)	H14B—C14—H14C	109.5
C4—C5—C6	117.90 (7)	O3—C15—H15A	109.5
C7—C6—C5	120.26 (8)	O3—C15—H15B	109.5
C7—C6—H6A	119.9	H15A—C15—H15B	109.5
C5—C6—H6A	119.9	O3—C15—H15C	109.5
C6—C7—C8	127.94 (8)	H15A—C15—H15C	109.5
C6—C7—H7A	116.0	H15B—C15—H15C	109.5
C8—C7—H7A	116.0	O4—C16—H16A	109.5
C9—C8—C13	120.22 (7)	O4—C16—H16B	109.5
C9—C8—C7	117.10 (7)	H16A—C16—H16B	109.5
C13—C8—C7	122.68 (7)	O4—C16—H16C	109.5
C10—C9—C8	120.15 (7)	H16A—C16—H16C	109.5
C10—C9—H9A	119.9	H16B—C16—H16C	109.5
C8—C9—H9A	119.9
C4—S1—C1—C2	−0.66 (8)	C14—O2—C10—C11	178.47 (7)
S1—C1—C2—C3	0.53 (11)	C8—C9—C10—O2	179.44 (8)
C1—C2—C3—C4	−0.06 (11)	C8—C9—C10—C11	−0.40 (12)
C2—C3—C4—C5	178.30 (9)	C15—O3—C11—C10	106.33 (9)
C2—C3—C4—S1	−0.43 (9)	C15—O3—C11—C12	−76.76 (10)
C1—S1—C4—C3	0.62 (7)	O2—C10—C11—O3	−2.98 (11)
C1—S1—C4—C5	−178.27 (7)	C9—C10—C11—O3	176.88 (8)
C3—C4—C5—O1	176.49 (10)	O2—C10—C11—C12	−179.93 (7)
S1—C4—C5—O1	−4.85 (13)	C9—C10—C11—C12	−0.07 (12)
C3—C4—C5—C6	−5.52 (14)	C16—O4—C12—C13	0.47 (12)
S1—C4—C5—C6	173.14 (7)	C16—O4—C12—C11	−179.67 (8)
O1—C5—C6—C7	10.94 (15)	O3—C11—C12—O4	3.51 (11)
C4—C5—C6—C7	−166.99 (8)	C10—C11—C12—O4	−179.59 (7)
C5—C6—C7—C8	176.81 (8)	O3—C11—C12—C13	−176.63 (8)
C6—C7—C8—C9	177.83 (9)	C10—C11—C12—C13	0.27 (12)
C6—C7—C8—C13	−3.34 (14)	O4—C12—C13—C8	179.86 (8)
C13—C8—C9—C10	0.69 (12)	C11—C12—C13—C8	0.01 (12)
C7—C8—C9—C10	179.55 (8)	C9—C8—C13—C12	−0.49 (12)
C14—O2—C10—C9	−1.38 (12)	C7—C8—C13—C12	−179.29 (8)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O1i	0.93	2.52	3.1827 (14)	129
C7—H7A···O1	0.93	2.48	2.8243 (12)	102
C15—H15B···O4	0.96	2.49	3.0396 (13)	116
C15—H15C···O3ii	0.96	2.39	3.3340 (11)	169
C7—H7A···O1	0.93	2.48	2.8243 (12)	102
C15—H15B···O4	0.96	2.49	3.0396 (13)	116

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O1i	0.93	2.52	3.1827 (14)	129
C15—H15C⋯O3ii	0.96	2.39	3.3340 (11)	169

Symmetry codes: (i) ; (ii) .