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

Asiri, A.M.; Khan, S.A.; Tahir, M.N.

doi:10.1107/S1600536810028709

organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page o2099

https://doi.org/10.1107/S1600536810028709

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

Abdullah M. Asiri,^a,^b Salman A. Khan ^b and M. Nawaz Tahir ^c ^*

^aThe Center of Excellence for Advanced Materials Research, King Abdul Aziz University, Jeddah 21589, PO Box 80203, Saudi Arabia, ^bDepartment of Chemistry, Faculty of Science, King Abdul Aziz University, Jeddah 21589, PO Box 80203, Saudi Arabia, and ^cUniversity of Sargodha, Department of Physics, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 12 July 2010; accepted 18 July 2010; online 24 July 2010)

In the title compound, C₁₈H₂₀O₄S, the thiophene and benzene rings are oriented at a dihedral angle of 10.83 (11)°. The central chain makes dihedral angles of 1.86 (13) and 9.25 (12)° with the benzene and thiophene rings, respectively. In the crystal, molecules are linked through weak intermolecular C—H⋯O interactions. π–π interactions are also observed between the benzene rings with a centroid–centroid distance of 3.6832 (12) Å. The slippage between the benzene rings is 0.956 Å.

Related literature

For the biological activity of 1,3-diphenyl-2-propene-1-ones, see: Gökhan-Kelekçi et al. (2007 ); Ducki et al. (2009 ); dos Santos et al. (2008 ); Hussain et al. (2009 ); Dandia et al. (2006 ); Valla et al. (2006 ); Ye et al. (2004 ). For related structures, see: Asiri et al. (2009 ): Hussain et al. (2010 ): Fun et al. (2010 ).

Experimental

Crystal data

C₁₈H₂₀O₄S
M_r = 332.40
Tetragonal, I 4₁ /a
a = 19.5263 (5) Å
c = 17.9952 (4) Å
V = 6861.2 (3) Å³
Z = 16
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 296 K
0.26 × 0.18 × 0.16 mm

Data collection

Bruker KAPPA APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.966, T_max = 0.975
25995 measured reflections
3106 independent reflections
2225 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.113
S = 1.05
3106 reflections
213 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9C⋯O3ⁱ	0.96	2.55	3.209 (3)	126
C14—H14⋯O4ⁱⁱ	0.93	2.57	3.483 (3)	168
Symmetry codes: (i) $[y+{\script{1\over 4}}, -x-{\script{1\over 4}}, -z+{\script{3\over 4}}]$ ; (ii) $[-y+{\script{1\over 4}}, x-{\script{1\over 4}}, z-{\script{1\over 4}}]$ .

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810028709/si2278sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810028709/si2278Isup2.hkl

checkCIF report

Comment top

1,3-Diphenyl-2-propene-1-one, are considered to be precursors of flavonoids when found as naturally occurring compounds, but it could be considered that their true importance is extended in two branches: The biological activity associated with them, including anti-inflammatory (Gökhan-Kelekçi et al., 2007), antimitotic (Ducki, et al., 2009), anti-leishmanial (dos Santos, et al., 2008), anti-invasive (Hussain, et al., 2009), anti-fungal (Dandia et al., 2006) antimalarial (Valla et al., 2006) and anti-tumor (Ye et al., 2004) properties; as well as their recognized synthetic utility in the preparation of pharmacologically interesting heterocyclic systems. On the bases of these aspects in this paper we are reporting the synthesis and crystal structure of the title compound (I), (Fig. 1).

The crystal structures of (II) i.e., (2E,2^'E)-1,1^'-bis(2,5-dimethyl-3-thienyl)-3,3^'-(p-phenylene) diprop-2-en-1-one (Asiri et al., 2009) has been published which contain the 2,5-dimethylthiophen-3-yl moiety. Similarly, the crystal structures of (III) 2,3-dimethyl-N-[(E)-2,4,5-trimethoxybenzylidene]aniline (Hussain et al., 2010) and (IV) 4-[(E)-(2,4,5-trimethoxybenzylidene)amino]-1,5-dimethyl-2- phenyl-1H-pyrazol-3(2H)-one (Fun et al., 2010) have been published which contain the 2,4,5-trimethoxyphenyl moiety.

In (I), the group A (C1—C6/O1/O2/O3) of 2,4,5-trimethoxyphenyl moiety, the central chain B (C10—C12/O4) and 2,5-dimethylthiophen-3-yl C (C13—C18/S1) are planar with r. m. s. deviation of 0.0033, 0.0160 and 0.0031 Å, respectively. The dihedral angle between A/B, A/C and B/C is 1.80 (10), 10.65 (9) and 9.23 (12)°, respectively. Overall 2,4,5-trimethoxyphenyl group has a maximum deviation 0.0338 Å and in it the C9 deviates at maximum 0.0834 (20) Å. The molecules are interlinked through H-bondings of C—H···O type (Table 1, Fig. 2). There exist π—π interaction between the centroids of phenyl rings at a distance of 3.6832 (12) Å [symmetry: - x, - y, 1 - z].

Related literature top

For the biological activity of 1,3-diphenyl-2-propene-1-ones, see: Gökhan-Kelekçi et al. (2007); Ducki et al. (2009); dos Santos et al. (2008); Hussain et al. (2009); Dandia et al. (2006); Valla et al. (2006); Ye et al. (2004). For related structures, see: Asiri et al. (2009): Hussain et al. (2010): Fun et al. (2010).

Experimental top

A solution of 3-acetyl-2,5-dimethythiophene (0.38 g, 0.0025 mol) and 2,4,5-trimethoxy benzaldehyde (0.49 g, 0.0025 mol) in ethanolic solution of NaOH (3.0 g in 10 ml of methanol) was stirred for 16 h at room temperature. The solution was poured into ice cold water of pH = 2 (pH adjusted by HCl). The solid was separated and dissolved in CH₂Cl₂, washed with saturated solution of NaHCO₃ and evaporated to dryness. The residual was recrystallized from methanol/chloroform to affoard yellow prisms.

Yield: 72%; m. p. 380–381 K.

IR (KBr) v_max cm^-1: 3016 (Ar—H), 2924 (C—H), 1642 (C═O), 1572(C═ C). 1H NMR (DMSO-d₆) (δ/p.p.m.): 8.01 (s, 1H, CH_aromatic), 7.98 (s, CH_aromatic), 7.20 (d, C═CH, J = 15.6 Hz), 7.08 (d, C═CH, J=15.0 Hz), 6.51 (s, 1H, C3, CH_thiophene), 3.94 (s, OCH₃), 3.73 (s, OCH₃), 3.62 (s, OCH₃),2.44 (s, 3H, –CH₃), 2.17 (s, 3H, CH₃).

Structure description top

For the biological activity of 1,3-diphenyl-2-propene-1-ones, see: Gökhan-Kelekçi et al. (2007); Ducki et al. (2009); dos Santos et al. (2008); Hussain et al. (2009); Dandia et al. (2006); Valla et al. (2006); Ye et al. (2004). For related structures, see: Asiri et al. (2009): Hussain et al. (2010): Fun et al. (2010).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with the atom numbering scheme. The thermal ellipsoids are drawn at the 50% probability level. H-atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The partial packing (PLATON; Spek, 2009) which shows that molecules are interlinked through H-bondings.

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

Crystal data top

C₁₈H₂₀O₄S	D_x = 1.287 Mg m⁻³
M_r = 332.40	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4₁/a	Cell parameters from 2225 reflections
Hall symbol: -I 4ad	θ = 2.1–25.2°
a = 19.5263 (5) Å	µ = 0.21 mm⁻¹
c = 17.9952 (4) Å	T = 296 K
V = 6861.2 (3) Å³	Prism, yellow
Z = 16	0.26 × 0.18 × 0.16 mm
F(000) = 2816

Data collection top

Bruker KAPPA APEXII CCD diffractometer	3106 independent reflections
Radiation source: fine-focus sealed tube	2225 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
Detector resolution: 8.10 pixels mm^-1	θ_max = 25.2°, θ_min = 2.1°
ω scans	h = −20→23
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −23→23
T_min = 0.966, T_max = 0.975	l = −21→21
25995 measured reflections

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.113	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0466P)² + 4.0141P] where P = (F_o² + 2F_c²)/3
3106 reflections	(Δ/σ)_max = 0.001
213 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₈H₂₀O₄S	Z = 16
M_r = 332.40	Mo Kα radiation
Tetragonal, I4₁/a	µ = 0.21 mm⁻¹
a = 19.5263 (5) Å	T = 296 K
c = 17.9952 (4) Å	0.26 × 0.18 × 0.16 mm
V = 6861.2 (3) Å³

Data collection top

Bruker KAPPA APEXII CCD diffractometer	3106 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2225 reflections with I > 2σ(I)
T_min = 0.966, T_max = 0.975	R_int = 0.038
25995 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.05	Δρ_max = 0.19 e Å⁻³
3106 reflections	Δρ_min = −0.15 e Å⁻³
213 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
S1	0.35094 (3)	0.20431 (3)	0.27680 (3)	0.0714 (2)
O1	0.12845 (9)	0.01126 (9)	0.64860 (7)	0.0807 (6)
O2	−0.03254 (9)	−0.15317 (9)	0.54859 (9)	0.0813 (6)
O3	0.00824 (9)	−0.12701 (10)	0.41648 (8)	0.0862 (7)
O4	0.27754 (9)	0.14060 (9)	0.50556 (8)	0.0818 (6)
C1	0.12078 (10)	−0.00807 (10)	0.52048 (10)	0.0514 (7)
C2	0.09748 (11)	−0.02371 (11)	0.59198 (10)	0.0556 (7)
C3	0.04661 (11)	−0.07194 (11)	0.60327 (11)	0.0600 (7)
C4	0.01787 (11)	−0.10560 (11)	0.54363 (12)	0.0600 (8)
C5	0.04047 (11)	−0.09097 (12)	0.47106 (11)	0.0604 (8)
C6	0.09028 (11)	−0.04341 (11)	0.46095 (11)	0.0569 (7)
C7	0.10721 (14)	−0.00049 (14)	0.72270 (11)	0.0754 (9)
C8	−0.05983 (14)	−0.16834 (16)	0.61946 (14)	0.0904 (11)
C9	0.03306 (14)	−0.12099 (15)	0.34337 (12)	0.0829 (10)
C10	0.17351 (10)	0.04257 (11)	0.51010 (10)	0.0553 (7)
C11	0.20201 (11)	0.06423 (11)	0.44711 (11)	0.0581 (7)
C12	0.25438 (11)	0.11732 (11)	0.44709 (11)	0.0579 (7)
C13	0.28009 (11)	0.14298 (11)	0.37456 (10)	0.0536 (7)
C14	0.25098 (12)	0.12648 (12)	0.30381 (11)	0.0622 (8)
C15	0.28342 (12)	0.15590 (12)	0.24581 (11)	0.0636 (8)
C16	0.26802 (14)	0.14998 (15)	0.16401 (12)	0.0857 (10)
C17	0.33529 (11)	0.18552 (11)	0.36833 (11)	0.0577 (7)
C18	0.38074 (14)	0.21495 (14)	0.42741 (13)	0.0810 (10)
H3	0.03178	−0.08165	0.65123	0.0720*
H6	0.10480	−0.03382	0.41285	0.0683*
H7A	0.05890	0.00783	0.72682	0.1132*
H7B	0.13148	0.02983	0.75542	0.1132*
H7C	0.11684	−0.04708	0.73613	0.1132*
H8A	−0.02460	−0.18752	0.65031	0.1355*
H8B	−0.09654	−0.20070	0.61437	0.1355*
H8C	−0.07688	−0.12709	0.64183	0.1355*
H9A	0.02961	−0.07418	0.32751	0.1242*
H9B	0.00640	−0.14950	0.31093	0.1242*
H9C	0.08010	−0.13520	0.34178	0.1242*
H10	0.18992	0.06293	0.55329	0.0664*
H11	0.18819	0.04507	0.40224	0.0697*
H14	0.21311	0.09805	0.29830	0.0747*
H16A	0.30512	0.12692	0.13955	0.1286*
H16B	0.26257	0.19491	0.14319	0.1286*
H16C	0.22655	0.12433	0.15719	0.1286*
H18A	0.35531	0.24738	0.45650	0.1215*
H18B	0.41902	0.23751	0.40458	0.1215*
H18C	0.39698	0.17880	0.45898	0.1215*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0843 (4)	0.0798 (4)	0.0502 (3)	−0.0019 (3)	0.0108 (3)	0.0054 (3)
O1	0.1053 (13)	0.0996 (12)	0.0372 (7)	−0.0388 (10)	−0.0040 (8)	−0.0007 (8)
O2	0.0825 (11)	0.0952 (12)	0.0662 (10)	−0.0260 (10)	0.0093 (8)	−0.0140 (9)
O3	0.0853 (12)	0.1182 (14)	0.0552 (9)	−0.0282 (10)	0.0079 (8)	−0.0337 (9)
O4	0.0953 (12)	0.1074 (13)	0.0426 (8)	−0.0294 (10)	−0.0032 (8)	−0.0034 (8)
C1	0.0545 (12)	0.0567 (12)	0.0430 (10)	0.0055 (10)	−0.0006 (8)	−0.0037 (9)
C2	0.0648 (13)	0.0599 (12)	0.0421 (10)	−0.0002 (11)	−0.0039 (9)	−0.0020 (9)
C3	0.0685 (14)	0.0697 (14)	0.0417 (10)	−0.0026 (12)	0.0018 (9)	0.0004 (10)
C4	0.0582 (13)	0.0642 (14)	0.0575 (12)	−0.0024 (11)	0.0040 (10)	−0.0072 (10)
C5	0.0594 (13)	0.0720 (14)	0.0497 (12)	0.0016 (12)	0.0015 (10)	−0.0171 (10)
C6	0.0582 (12)	0.0691 (14)	0.0434 (10)	0.0050 (11)	0.0060 (9)	−0.0084 (9)
C7	0.0982 (18)	0.0905 (17)	0.0376 (11)	−0.0146 (14)	−0.0026 (11)	0.0011 (10)
C8	0.093 (2)	0.104 (2)	0.0743 (16)	−0.0267 (17)	0.0136 (14)	0.0047 (14)
C9	0.0979 (19)	0.100 (2)	0.0507 (13)	−0.0002 (16)	−0.0021 (12)	−0.0240 (12)
C10	0.0624 (13)	0.0620 (13)	0.0416 (10)	0.0028 (10)	−0.0034 (9)	−0.0044 (9)
C11	0.0659 (13)	0.0673 (14)	0.0411 (10)	−0.0020 (11)	−0.0016 (9)	−0.0048 (9)
C12	0.0644 (13)	0.0685 (14)	0.0408 (10)	0.0026 (11)	−0.0012 (9)	−0.0016 (9)
C13	0.0584 (12)	0.0586 (12)	0.0439 (10)	0.0069 (10)	0.0009 (9)	0.0003 (9)
C14	0.0656 (14)	0.0786 (15)	0.0425 (11)	0.0027 (11)	−0.0005 (10)	−0.0003 (10)
C15	0.0700 (14)	0.0767 (15)	0.0440 (11)	0.0121 (12)	0.0002 (10)	−0.0011 (10)
C16	0.0957 (19)	0.120 (2)	0.0414 (12)	0.0123 (16)	−0.0012 (12)	0.0040 (12)
C17	0.0666 (14)	0.0611 (13)	0.0454 (11)	0.0065 (11)	0.0041 (9)	−0.0021 (9)
C18	0.0866 (18)	0.0967 (19)	0.0597 (14)	−0.0225 (15)	0.0038 (12)	−0.0086 (13)

Geometric parameters (Å, º) top

S1—C15	1.715 (2)	C15—C16	1.507 (3)
S1—C17	1.715 (2)	C17—C18	1.499 (3)
O1—C2	1.368 (2)	C3—H3	0.9300
O1—C7	1.415 (2)	C6—H6	0.9300
O2—C4	1.356 (3)	C7—H7A	0.9600
O2—C8	1.414 (3)	C7—H7B	0.9600
O3—C5	1.362 (3)	C7—H7C	0.9600
O3—C9	1.407 (3)	C8—H8A	0.9600
O4—C12	1.232 (3)	C8—H8B	0.9600
C1—C2	1.399 (3)	C8—H8C	0.9600
C1—C6	1.407 (3)	C9—H9A	0.9600
C1—C10	1.440 (3)	C9—H9B	0.9600
C2—C3	1.384 (3)	C9—H9C	0.9600
C3—C4	1.378 (3)	C10—H10	0.9300
C4—C5	1.408 (3)	C11—H11	0.9300
C5—C6	1.357 (3)	C14—H14	0.9300
C10—C11	1.332 (3)	C16—H16A	0.9600
C11—C12	1.456 (3)	C16—H16B	0.9600
C12—C13	1.486 (3)	C16—H16C	0.9600
C13—C14	1.431 (3)	C18—H18A	0.9600
C13—C17	1.365 (3)	C18—H18B	0.9600
C14—C15	1.349 (3)	C18—H18C	0.9600

O2···O3	2.559 (2)	H6···C9	2.5300
O2···C9ⁱ	3.410 (3)	H6···C11	2.7700
O3···O2	2.559 (2)	H6···H9A	2.2700
O3···C9ⁱ	3.209 (3)	H6···H9C	2.4100
O4···C18	2.854 (3)	H6···H11	2.2500
O1···H10	2.3200	H6···H10^viii	2.5900
O3···H9Cⁱ	2.5500	H7A···C3	2.7300
O4···H10	2.4400	H7A···H3	2.2800
O4···H18A	2.7300	H7A···H9A^iv	2.3700
O4···H18C	2.5900	H7B···C16^v	2.9300
O4···H8Cⁱⁱ	2.7600	H7B···H16A^v	2.4700
O4···H9Aⁱⁱⁱ	2.8400	H7B···C1ⁱⁱⁱ	2.9100
O4···H14ⁱⁱⁱ	2.5700	H7B···C6ⁱⁱⁱ	3.0400
C4···C6^iv	3.596 (3)	H7C···C3	2.8000
C6···C4^iv	3.596 (3)	H7C···H3	2.3600
C7···C16^v	3.464 (3)	H7C···C15^ix	2.8900
C9···O3^vi	3.209 (3)	H8A···C3	2.7800
C9···O2^vi	3.410 (3)	H8A···H3	2.3400
C16···C7^vii	3.464 (3)	H8C···C3	2.7300
C18···O4	2.854 (3)	H8C···H3	2.3100
C1···H7B^viii	2.9100	H8C···O4^xiii	2.7600
C2···H16A^ix	2.9000	H9A···C6	2.7400
C3···H8C	2.7300	H9A···H6	2.2700
C3···H8A	2.7800	H9A···H7A^iv	2.3700
C3···H7A	2.7300	H9A···O4^viii	2.8400
C3···H7C	2.8000	H9C···C6	2.8000
C6···H7B^viii	3.0400	H9C···H6	2.4100
C6···H9C	2.8000	H9C···O3^vi	2.5500
C6···H11	2.7800	H10···O1	2.3200
C6···H9A	2.7400	H10···O4	2.4400
C7···H3	2.5200	H10···H6ⁱⁱⁱ	2.5900
C8···H3	2.5300	H11···C6	2.7800
C9···H6	2.5300	H11···C14	2.6800
C11···H6	2.7700	H11···H6	2.2500
C11···H14	2.7700	H11···H14	2.1900
C12···H14ⁱⁱⁱ	3.0200	H14···C11	2.7700
C12···H18C	3.0400	H14···H11	2.1900
C12···H16Cⁱⁱⁱ	3.0600	H14···O4^viii	2.5700
C13···H16Cⁱⁱⁱ	3.0300	H14···C12^viii	3.0200
C14···H11	2.6800	H16A···C2^x	2.9000
C15···H7C^x	2.8900	H16A···H7B^vii	2.4700
C16···H7B^vii	2.9300	H16B···C17^xi	3.0200
C17···H16B^xi	3.0200	H16C···C12^viii	3.0600
C18···H18B^xii	3.1000	H16C···C13^viii	3.0300
H3···C7	2.5200	H18A···O4	2.7300
H3···C8	2.5300	H18B···C18^xiv	3.1000
H3···H7A	2.2800	H18B···H18B^xiv	2.5000
H3···H7C	2.3600	H18B···H18B^xii	2.5000
H3···H8A	2.3400	H18C···O4	2.5900
H3···H8C	2.3100	H18C···C12	3.0400

C15—S1—C17	93.29 (10)	O1—C7—H7A	109.00
C2—O1—C7	119.44 (18)	O1—C7—H7B	109.00
C4—O2—C8	118.45 (19)	O1—C7—H7C	109.00
C5—O3—C9	118.16 (19)	H7A—C7—H7B	109.00
C2—C1—C6	117.12 (18)	H7A—C7—H7C	109.00
C2—C1—C10	120.13 (17)	H7B—C7—H7C	109.00
C6—C1—C10	122.75 (17)	O2—C8—H8A	109.00
O1—C2—C1	115.63 (18)	O2—C8—H8B	109.00
O1—C2—C3	123.22 (17)	O2—C8—H8C	109.00
C1—C2—C3	121.15 (18)	H8A—C8—H8B	109.00
C2—C3—C4	120.17 (19)	H8A—C8—H8C	109.00
O2—C4—C3	124.82 (19)	H8B—C8—H8C	109.00
O2—C4—C5	115.31 (19)	O3—C9—H9A	109.00
C3—C4—C5	119.9 (2)	O3—C9—H9B	109.00
O3—C5—C4	114.78 (19)	O3—C9—H9C	109.00
O3—C5—C6	126.01 (19)	H9A—C9—H9B	109.00
C4—C5—C6	119.20 (19)	H9A—C9—H9C	109.00
C1—C6—C5	122.49 (18)	H9B—C9—H9C	109.00
C1—C10—C11	128.86 (18)	C1—C10—H10	116.00
C10—C11—C12	121.32 (19)	C11—C10—H10	116.00
O4—C12—C11	121.34 (19)	C10—C11—H11	119.00
O4—C12—C13	120.12 (19)	C12—C11—H11	119.00
C11—C12—C13	118.53 (18)	C13—C14—H14	123.00
C12—C13—C14	124.86 (19)	C15—C14—H14	123.00
C12—C13—C17	122.97 (18)	C15—C16—H16A	109.00
C14—C13—C17	112.18 (18)	C15—C16—H16B	109.00
C13—C14—C15	114.0 (2)	C15—C16—H16C	109.00
S1—C15—C14	110.12 (16)	H16A—C16—H16B	109.00
S1—C15—C16	120.88 (17)	H16A—C16—H16C	109.00
C14—C15—C16	129.0 (2)	H16B—C16—H16C	109.00
S1—C17—C13	110.47 (15)	C17—C18—H18A	109.00
S1—C17—C18	119.58 (17)	C17—C18—H18B	109.00
C13—C17—C18	129.96 (19)	C17—C18—H18C	109.00
C2—C3—H3	120.00	H18A—C18—H18B	109.00
C4—C3—H3	120.00	H18A—C18—H18C	109.00
C1—C6—H6	119.00	H18B—C18—H18C	109.00
C5—C6—H6	119.00

C17—S1—C15—C14	−0.40 (19)	O2—C4—C5—O3	−0.1 (3)
C17—S1—C15—C16	−179.6 (2)	O2—C4—C5—C6	179.3 (2)
C15—S1—C17—C13	0.38 (18)	C3—C4—C5—O3	−179.7 (2)
C15—S1—C17—C18	179.9 (2)	C3—C4—C5—C6	−0.3 (3)
C7—O1—C2—C1	178.9 (2)	O3—C5—C6—C1	179.6 (2)
C7—O1—C2—C3	−1.5 (3)	C4—C5—C6—C1	0.3 (3)
C8—O2—C4—C3	2.2 (3)	C1—C10—C11—C12	178.9 (2)
C8—O2—C4—C5	−177.3 (2)	C10—C11—C12—O4	5.2 (3)
C9—O3—C5—C4	−173.0 (2)	C10—C11—C12—C13	−175.2 (2)
C9—O3—C5—C6	7.6 (3)	O4—C12—C13—C14	−171.4 (2)
C6—C1—C2—O1	179.65 (19)	O4—C12—C13—C17	8.8 (3)
C6—C1—C2—C3	0.0 (3)	C11—C12—C13—C14	9.0 (3)
C10—C1—C2—O1	−0.7 (3)	C11—C12—C13—C17	−170.8 (2)
C10—C1—C2—C3	179.7 (2)	C12—C13—C14—C15	−179.9 (2)
C2—C1—C6—C5	−0.2 (3)	C17—C13—C14—C15	0.0 (3)
C10—C1—C6—C5	−179.8 (2)	C12—C13—C17—S1	179.55 (17)
C2—C1—C10—C11	−180.0 (2)	C12—C13—C17—C18	0.2 (4)
C6—C1—C10—C11	−0.3 (3)	C14—C13—C17—S1	−0.3 (2)
O1—C2—C3—C4	−179.6 (2)	C14—C13—C17—C18	−179.7 (2)
C1—C2—C3—C4	0.0 (3)	C13—C14—C15—S1	0.3 (3)
C2—C3—C4—O2	−179.4 (2)	C13—C14—C15—C16	179.4 (2)
C2—C3—C4—C5	0.2 (3)

Symmetry codes: (i) −y−1/4, x−1/4, −z+3/4; (ii) −y+1/4, x+1/4, −z+5/4; (iii) y+1/4, −x+1/4, z+1/4; (iv) −x, −y, −z+1; (v) −y+1/4, x−1/4, z+3/4; (vi) y+1/4, −x−1/4, −z+3/4; (vii) y+1/4, −x+1/4, z−3/4; (viii) −y+1/4, x−1/4, z−1/4; (ix) −x+1/2, −y, z+1/2; (x) −x+1/2, −y, z−1/2; (xi) −x+1/2, −y+1/2, −z+1/2; (xii) −y+3/4, x−1/4, −z+3/4; (xiii) y−1/4, −x+1/4, −z+5/4; (xiv) y+1/4, −x+3/4, −z+3/4.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9C···O3^vi	0.96	2.55	3.209 (3)	126
C14—H14···O4^viii	0.93	2.57	3.483 (3)	168

Symmetry codes: (vi) y+1/4, −x−1/4, −z+3/4; (viii) −y+1/4, x−1/4, z−1/4.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₀O₄S
M_r	332.40
Crystal system, space group	Tetragonal, I4₁/a
Temperature (K)	296
a, c (Å)	19.5263 (5), 17.9952 (4)
V (Å³)	6861.2 (3)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.26 × 0.18 × 0.16

Data collection
Diffractometer	Bruker KAPPA APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.966, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	25995, 3106, 2225
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.113, 1.05
No. of reflections	3106
No. of parameters	213
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.15

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9C···O3ⁱ	0.96	2.55	3.209 (3)	126
C14—H14···O4ⁱⁱ	0.93	2.57	3.483 (3)	168

Symmetry codes: (i) y+1/4, −x−1/4, −z+3/4; (ii) −y+1/4, x−1/4, z−1/4.

Acknowledgements

The authors would like to thank the Chemistry Department, King Abdul Aziz University, Jeddah, Saudi Arabia for providing research facilities and the Deanship of Scientific Research for the financial support of this work via grant No. (3–045/430).

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