(E)-1-(2-Thien­yl)-3-(3,4,5-trimethoxy­phen­yl)prop-2-en-1-one

Suwunwong, T.; Chantrapromma, S.; Pakdeevanich, P.; Fun, H.-K.

doi:10.1107/S1600536809021850

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Pages o1575-o1576

doi:10.1107/S1600536809021850

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(E)-1-(2-Thienyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one †

Thitipone Suwunwong,^a Suchada Chantrapromma,^a ^*‡ Paradorn Pakdeevanich ^b and Hoong-Kun Fun ^c §

^aCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, ^bDepartment of Physics, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: suchada.c@psu.ac.th

(Received 21 May 2009; accepted 9 June 2009; online 13 June 2009)

The molecule of the title heteroaryl chalcone, C₁₆H₁₆O₄S, which consists of substituted thiophene and benzene rings bridged by the prop-2-en-1-one group, is slightly twisted. The dihedral angle between the thiophene and 3,4,5-trimethoxyphenyl rings is 12.18 (4)°. The three methoxy groups have two different conformations; two methoxy 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 molecules are linked in a face-to-side manner into chains along the c axis by weak C—H⋯O(enone) interactions. These chains are stacked along the b axis by weak C—H⋯O(methoxy) interactions.

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_r = 304.36
Orthorhombic, P n a 2₁
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[F² > 2σ(F²)] = 0.033
wR(F²) = 0.099
S = 1.10
7416 reflections
193 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.66 e Å⁻³
Δρ_min = −0.54 e Å⁻³
Absolute structure: Flack (1983 ), 3588 Friedel pairs
Flack parameter: 0.04 (4)

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) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x, y-1, z.

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 ).

Supporting information

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

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

checkCIF report

Comment top

Chalcone or 1,3-diaryl-2-propen-1-one, originally isolated from natural sources, and its derivatives are known to display a variety of biological activities, demonstrating analgesic, anti-inflammatory, antibacterial and antimycotic properties (Dimmock et al., 1999; Go et al., 2005; Ni et al., 2004). Moreover synthetic chalcones have also been found to be non-linear optical (NLO) (Patil & Dharmaprakash, 2008) and electro-active fluorescent materials (Jung et al., 2008). We have previously reported the synthesis and crystal structures of chalcone derivatives (Chantrapromma et al., 2009; Suwunwong et al., 2009a, b). Our research into the NLO and biological properties of chalcone derivatives led us to synthesize the title heteroaryl chalcone (I). (I) crystallizes in the non-centrosymmetric orthorhombic space group Pna2₁ and should therefore exhibit second-order nonlinear optical properties.

The molecule of the title heteroaryl chalcone (Fig. 1) exists in an E configuration with respect to the C6═C7 double bond [1.3437 (11) Å] with a C5–C6–C7–C8 torsion angle 176.81 (8)°. The whole molecule is twisted as shown by the interplanar angle between thiophene and 3,4,5-trimethoxyphenyl rings being 12.18 (4)°. The propenone unit (C5—C7/O1) is also twisted with the O1–C5–C6–C7 torsion angle 10.94 (15)°. The three substituted methoxy groups of 3,4,5-trimethoxyphenyl unit have two different orientations: two methoxy groups (at the C10 and C12 positions) are co-planar with the phenyl ring with torsion angles C14–O2–C10–C9 = -1.38 (12)° and C16–O4–C12–C13 = 0.47 (12)° whereas the one at C11 is (-)-syn-clinally attached with the C15–O3–C11–C12 torsion angle -76.76 (10)°. In the structure, weak intramolecular C7—H7A···O1 and C15—H15B···O4 interactions generate S(5) and S(6) ring motifs, respectively (Bernstein et al., 1995). The bond distances have normal values (Allen et al., 1987) and bond lengths and angles are comparable with closely related structures (Chantrapromma et al., 2009; Patil et al., 2006; 2007; Suwunwong et al., 2009a, b).

In the crystal packing, the adjacent molecules are linked in a face-to-side manner into chains along the c axis through the enone unit by weak C1—H1A···O1 interactions (Fig. 2, Table 1). Weak C15—H15C···O3 interactions involving one of methoxy groups further stack these chains along the b axis (Fig. 3, Table 1).

Related literature top

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 top

The title compound was synthesized by the condensation of 3,4,5-trimethoxybenzaldehyde (0.40 g, 2 mmol) with 2-acetylthiophene (0.35 ml, 2 mmol) in ethanol (30 ml) in the presence of 30% NaOH (aq) (5 ml). After stirring for 3 h in ice bath at 278 K, the resulting pale yellow solid was collected by filtration, washed with distilled water, dried in air and purified by repeated recrystallization from acetone (72% yield). Pale yellow block-shaped single crystals of the title compound suitable for x-ray structure determination were recrystalized from acetone/ethanol (1:1 v/v) by the slow evaporation of the solvent at room temperature after several days, Mp. 420–421 K.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The crystal packing of the title compound viewed along the b axis, showing chains running along the c axis. Weak C—H···O interactions are shown as dashed lines.
	Fig. 3. The crystal packing of the title compound viewed along the a axis, showing chains stacking along the b axis. Weak C—H···O interactions are shown as dashed lines and hydrogen atoms not involved in C—H···O interactions were omitted for clarity.

(E)-1-(2-Thienyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one top

Crystal data top

C₁₆H₁₆O₄S	D_x = 1.430 Mg m⁻³
M_r = 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

Data collection top

Bruker APEXII CCD area-detector diffractometer	7416 independent reflections
Radiation source: sealed tube	7177 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ϕ and ω scans	θ_max = 37.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −43→43
T_min = 0.872, T_max = 0.951	k = −6→6
56940 measured reflections	l = −23→24

Refinement top

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(F_o²) + (0.0672P)² + 0.1429P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max = 0.001
7416 reflections	Δρ_max = 0.66 e Å⁻³
193 parameters	Δρ_min = −0.54 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 3588 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (4)

Crystal data top

C₁₆H₁₆O₄S	V = 1413.73 (7) Å³
M_r = 304.36	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 25.3323 (8) Å	µ = 0.24 mm⁻¹
b = 3.9816 (1) Å	T = 100 K
c = 14.0163 (4) Å	0.58 × 0.31 × 0.21 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	7416 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	7177 reflections with I > 2σ(I)
T_min = 0.872, T_max = 0.951	R_int = 0.028
56940 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.099	Δρ_max = 0.66 e Å⁻³
S = 1.10	Δρ_min = −0.54 e Å⁻³
7416 reflections	Absolute structure: Flack (1983), 3588 Friedel pairs
193 parameters	Absolute structure parameter: 0.04 (4)
1 restraint

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x+1/2, y+1/2, z−1/2; (ii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆O₄S
M_r	304.36
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	100
a, b, c (Å)	25.3323 (8), 3.9816 (1), 14.0163 (4)
V (Å³)	1413.73 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.58 × 0.31 × 0.21

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.872, 0.951
No. of measured, independent and observed [I > 2σ(I)] reflections	56940, 7416, 7177
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.857

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.099, 1.10
No. of reflections	7416
No. of parameters	193
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.66, −0.54
Absolute structure	Flack (1983), 3588 Friedel pairs
Absolute structure parameter	0.04 (4)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x+1/2, y+1/2, z−1/2; (ii) x, y−1, z.

Footnotes

†This paper is dedicated to the late Her Royal Highness Princess Galyani Vadhana Krom Luang Naradhiwas Rajanagarindra for her patronage of Science in Thailand.

‡Thomson Reuters ResearcherID: A-5085-2009.

§Additional correspondence author, e-mail: hkfun@usm.my; Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

Financial support from the Prince of Songkla University through the Crystal Materials Research Unit is gratefully acknowledged. TS thanks the Graduate School, Prince of Songkla University, for partial financial support. The authors also thank Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

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