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

Fun, H.-K.; Jebas, S.R.; Patil, P.S.; Dharmaprakash, S.M.

doi:10.1107/S1600536808021375

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Pages o1510-o1511

doi:10.1107/S1600536808021375

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

Hoong-Kun Fun,^a ^* Samuel Robinson Jebas,^a ‡ P. S. Patil ^b and S. M. Dharmaprakash ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Studies in Physics, Mangalore University, Mangalagangotri, Mangalore 574 199, India
^*Correspondence e-mail: hkfun@usm.my

(Received 9 July 2008; accepted 9 July 2008; online 16 July 2008)

In the title molecule, C₁₆H₁₆O₄S, the enone fragment, thiophene ring and benzene ring are individually essentially planar. The thiophene 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 thiophene ring and the benzene ring are twisted from each other by 13.92 (19)°. An intramolecular C—H⋯O hydrogen bond generates an S(5)S(5) ring motif. The crystal structure is stabilized by intermolecular C—H⋯O hydrogen-bonding interactions. In addition, a π–π stacking interaction, 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_r = 304.35
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.045
wR(F²) = 0.120
S = 1.07
4256 reflections
211 parameters
120 restraints
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.22 e Å⁻³

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) x, y+1, z; (ii) -x+1, -y-1, -z.

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 ).

Supporting information

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

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

checkCIF report

Comment top

The title compound (I) has been synthesized as part of our crystallographic studies on nonlinear optical materials (Chantrapromma et al., 2005, 2006; Fun et al., 2006; Patil, Fun et al., 2007; Patil, Dharmaprakash et al., 2007). We report herein the crystal structure of the title compound, (I).

In the title molecular structure (I), the thiophene ring is disordered over two sites (atoms of the minor occupancy component are labelled with the suffix X), corresponding to a rotation of approximately 180° about the C4—C5 bond. The bond lengths and bond angles are found to have normal values (Allen et al., 1987) and agree with a related structure (Patil et al., 2006) with the execption of some parameters of the thiophene ring, which are probably a consequence of the disorder. The benzene and thiophene rings are individually planar, with maximum deviations of 0.019 (2) Å for atom C12 and -0.074 (2)Å for atom C1X. The molecule is twisted about the C7—C8 bond with a dihedral angle of 13.93 (19)° between the benzene ring and S1/C1—C4 [15.9 (19)° for S1X/C1X—C3X].

Intramolecular hydrogen bond C—H···O generates ring motif S(5)S(5) (Bernstein et al., 1995). The crystal packing is stabilized by intra and intermolecular C—H···O interactions. π—π interactions between the S1/C1—C4 (centroid Cg1) and C8—C13 (centroid Cg3) rings [Cg1···Cg3ⁱ=3.852 (2) Å] [symmetry code: (i) -x,-y,-z] together with S···O=2.9378 (12)Å and O···O=2.5811 (16)Å short contacts are observed.

Related literature top

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 top

2,4,5-trimethoxybenzaldehyde (0.01 mol, 1.96 g m) in ethanol (30 ml) was mixed with 2-acetylthiophene (0.01 mol, 1.07 ml) in 30 ml ethanol and the mixture was treated with 10 ml of 10% sodium hydroxide solution and stirred at room temperature for 8 h. The precipitate obtained was poured into ice-cold water (500 ml) and left to stand for 5 h. The resulting crude solid was filtered, dried and recrystallized from N, N-dimethylformamide (DMF) by slow evaporation.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (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, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom numbering scheme. Open bonds indicate the minor disorder component. Dashed lines indicate hydrogen bonds.
	Fig. 2. The crystal packing of the major component of the title compound,viewed along the c axis. Hydrogen bonds are shown as dashed lines.
	Fig. 3. The crystal packing of the minor component of the title compound, viewed along the c axis. Hydrogen bonds are shown as dashed lines.

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

Crystal data top

C₁₆H₁₆O₄S	F(000) = 640
M_r = 304.35	D_x = 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 = 7.5391 (1) Å	θ = 2.7–28.4°
b = 7.9225 (1) Å	µ = 0.24 mm⁻¹
c = 24.3399 (3) Å	T = 100 K
β = 97.021 (1)°	Block, yellow
V = 1442.88 (3) Å³	0.25 × 0.22 × 0.14 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4256 independent reflections
Radiation source: fine-focus sealed tube	3174 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
ϕ and ω scans	θ_max = 30.1°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→10
T_min = 0.942, T_max = 0.967	k = −11→10
33027 measured reflections	l = −34→34

Refinement top

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0532P)² + 0.4695P] where P = (F_o² + 2F_c²)/3
4256 reflections	(Δ/σ)_max < 0.001
211 parameters	Δρ_max = 0.41 e Å⁻³
120 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₆H₁₆O₄S	V = 1442.88 (3) Å³
M_r = 304.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.5391 (1) Å	µ = 0.24 mm⁻¹
b = 7.9225 (1) Å	T = 100 K
c = 24.3399 (3) Å	0.25 × 0.22 × 0.14 mm
β = 97.021 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4256 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3174 reflections with I > 2σ(I)
T_min = 0.942, T_max = 0.967	R_int = 0.063
33027 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	120 restraints
wR(F²) = 0.120	H-atom parameters constrained
S = 1.07	Δρ_max = 0.41 e Å⁻³
4256 reflections	Δρ_min = −0.22 e Å⁻³
211 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, y+1, z; (ii) −x+1, −y−1, −z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆O₄S
M_r	304.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	7.5391 (1), 7.9225 (1), 24.3399 (3)
β (°)	97.021 (1)
V (Å³)	1442.88 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.25 × 0.22 × 0.14

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.942, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	33027, 4256, 3174
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.706

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.120, 1.07
No. of reflections	4256
No. of parameters	211
No. of restraints	120
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.22

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

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) x, y+1, z; (ii) −x+1, −y−1, −z.

Footnotes

‡Permanent address: Department of Physics, Karunya University, Karunya Nagar, Coimbatore 641 114, India.

Acknowledgements

HKF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks Universiti Sains Malaysia for a post-doctoral research fellowship. This work was supported by the Department of Science and Technology (DST), Government of India (grant No. SR/S2/LOP-17/2006).

References

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