Diethyl 3,4-dimethyl­thieno[2,3-b]thio­phene-2,5-dicarboxyl­ate

Akkurt, M.; Kennedy, A.R.; Younes, S.H.H.; Mohamed, S.K.; Miller, G.J.

doi:10.1107/S160053681204593X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 12| December 2012| Pages o3332-o3333

doi:10.1107/S160053681204593X

Open

access

Diethyl 3,4-dimethylthieno[2,3-b]thiophene-2,5-dicarboxylate

Mehmet Akkurt,^a ^* Alan R. Kennedy,^b ^* Sabry H. H. Younes,^c Shaaban K. Mohamed ^d,^e and Gary J. Miller ^f ^*

^aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^bDepartment of Pure & Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, Scotland, ^cDepartment of Chemistry, Faculty of Science, Sohag University, 82524 Sohag, Egypt, ^dChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^eChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, and ^fAnalytical Sciences, Manchester Metropolitan University, Manchester M1 5GD, England
^*Correspondence e-mail: akkurt@erciyes.edu.tr, a.r.Kennedy@strath.ac.uk, G.Miller@mmu.ac.uk

(Received 6 November 2012; accepted 7 November 2012; online 10 November 2012)

In the title compound, C₁₄H₁₆O₄S₂, the thieno[2,3-b]thiophene ring systems are planar [maximum deviation = 0.008 (2) Å]. The molecular conformation is stabilized by intramolecular C—H⋯O hydrogen bonds, while the crystal packing is stabilized by C—H⋯O, C—H⋯π and π–π stacking [centroid–centroid distance = 3.6605 (14) Å] interactions, which lead to supramolecular layers in the ab plane.

Related literature

For the use of thienthiophenes as versatile precursors for the synthesis of various heterocycles, see: Mabkhot et al. (2010 , 2012 ); Litvinov (2005 ). For their industrial applications, see: Lee & Sotzing (2001 ); Heeney et al. (2005 ); Gather et al. (2008 ); He et al. (2009 ). For pharmaceutical values of thieno[2,3-b]thiophenes, see: Jarak et al. (2006 ); Egbertson et al. (1999 ). For bond lengths and bond angles in similar compounds, see: Umadevi et al. (2009 ); Gunasekaran et al. (2009 ); Wang et al. (2008 ). For the synthesis of the title compound, see: Comel & Kirsch (2001a ,b ). For graph-set descriptions of hydrogen-bond ring motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₄H₁₆O₄S₂
M_r = 312.39
Triclinic, $[P \overline 1]$
a = 7.3497 (3) Å
b = 8.4720 (4) Å
c = 12.8629 (5) Å
α = 102.770 (3)°
β = 99.545 (3)°
γ = 107.779 (4)°
V = 719.96 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.38 mm⁻¹
T = 123 K
0.30 × 0.08 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.966, T_max = 1.000
6901 measured reflections
3486 independent reflections
2661 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.106
S = 1.04
3486 reflections
185 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the S2/C1–C4 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯O1	0.98	2.22	2.980 (3)	133
C8—H8A⋯O3	0.98	2.23	2.909 (3)	125
C11—H11A⋯O4ⁱ	0.98	2.53	3.471 (3)	161
C8—H8C⋯Cg2ⁱⁱ	0.98	2.74	3.578 (3)	144
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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, 2012 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681204593X/tk5168sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681204593X/tk5168Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681204593X/tk5168Isup3.cml

checkCIF report

Comment top

Thienothiophene compounds are a great class of sulfur heterocyclic chemistry due their utilities in various applications in industrial and medicinal fields. They have wide variety applications in optical and electronic systems (Gather et al., 2008; He et al., 2009). Besides, thieno[2,3-b]thiophenes showed useful reactivities as co-polymerization agents (Lee & Sotzing, 2001) and as semiconductors (Heeney et al., 2005). They have been developed and tested as potential antitumor, antiviral, antiglaucoma drugs, antiproliferation agents, or as inhibitors of platelet aggregation (Jarak et al., 2006; Egbertson et al., 1999). In addition, thienothiophenes have been used as versatile precursors for synthesis of various heterocycles (Mabkhot et al., 2012, Mabkhot et al., 2010; Litvinov, 2005). In view of such important applications, we herein report the crystal structure determination of the title compound (I) to investigate the relationship between its structure and antibacterial activity.

In the title compound, C₁₄H₁₆O₄S₂, the thieno[2,3-b]thiophene ring systems are planar with a maximum deviation of 0.008 (2) Å for C2. The values of the bond lengths and bond angles in (I) are in the normal range and comparable to those reported for the similar compounds (Umadevi et al., 2009; Gunasekaran et al., 2009; Wang et al., 2008). The O1–C9–C2–S2, O2–C9–C2–S2, O3–C12–C6–S1 and O4–C12–C6–S1 bond angles are 175.95 (19), -4.8 (3), 176.14 (16) and 4.0 (3)°, respectively.

The intramolecular C7—H7A···O1 and C8—H8A···O3 interactions form six- membered rings, producing S(6) ring motif (Table 1; Bernstein et al., 1995). In the crystal, the molecules are linked by intermolecular C—H···O hydrogen bonds (Table 1, Fig. 2), and are further consolidated by C—H···π interactions and π-π stacking [Cg1···Cg1(-x, 1 - y, 1 - z) = 3.6605 (14) Å; where Cg1 is a centroid of the S1/C1/C4–C6 ring] interactions.

Related literature top

For the use of thienthiophenes as versatile precursors for the synthesis of various heterocycles, see: Mabkhot et al. (2010, 2012); Litvinov (2005). For their industrial applications, see: Lee & Sotzing (2001); Heeney et al. (2005); Gather et al. (2008); He et al. (2009). For pharmaceutical values of thieno[2,3-b]thiophenes, see: Jarak et al. (2006); Egbertson et al. (1999). For bond lengths and bond angles in similar compounds, see: Umadevi et al. (2009); Gunasekaran et al. (2009); Wang et al. (2008). For the synthesis of the title compound, see: Comel & Kirsch (2001a,b). For graph-set descriptions of hydrogen-bond ring motifs, see: Bernstein et al. (1995).

Experimental top

The title compound was prepared according to the reported method in literature (Comel & Kirsch, 2001a,b). Single crystals suitable for X-ray analysis were grown in an ethanol solution of (I) at room temperature over 24 h. M.pt: 413 K.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); 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, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the molecular structure of (I) with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
	Fig. 2. View of the packing and hydrogen bonding of (I) down the a axis. H atoms not involved in hydrogen bonds have been omitted for clarity.

Diethyl 3,4-dimethylthieno[2,3-b]thiophene-2,5-dicarboxylate top

Crystal data top

C₁₄H₁₆O₄S₂	Z = 2
M_r = 312.39	F(000) = 328
Triclinic, P1	D_x = 1.441 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3497 (3) Å	Cell parameters from 2806 reflections
b = 8.4720 (4) Å	θ = 3.2–29.4°
c = 12.8629 (5) Å	µ = 0.38 mm⁻¹
α = 102.770 (3)°	T = 123 K
β = 99.545 (3)°	Rod, colourless
γ = 107.779 (4)°	0.30 × 0.08 × 0.06 mm
V = 719.96 (6) Å³

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	3486 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2661 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
Detector resolution: 16.0727 pixels mm^-1	θ_max = 29.5°, θ_min = 3.2°
ω scans	h = −9→10
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −11→11
T_min = 0.966, T_max = 1.000	l = −17→17
6901 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0365P)² + 0.4173P] where P = (F_o² + 2F_c²)/3
3486 reflections	(Δ/σ)_max = 0.002
185 parameters	Δρ_max = 0.53 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₄H₁₆O₄S₂	γ = 107.779 (4)°
M_r = 312.39	V = 719.96 (6) Å³
Triclinic, P1	Z = 2
a = 7.3497 (3) Å	Mo Kα radiation
b = 8.4720 (4) Å	µ = 0.38 mm⁻¹
c = 12.8629 (5) Å	T = 123 K
α = 102.770 (3)°	0.30 × 0.08 × 0.06 mm
β = 99.545 (3)°

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	3486 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	2661 reflections with I > 2σ(I)
T_min = 0.966, T_max = 1.000	R_int = 0.025
6901 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.04	Δρ_max = 0.53 e Å⁻³
3486 reflections	Δρ_min = −0.34 e Å⁻³
185 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 on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.19179 (8)	0.66605 (7)	0.37995 (4)	0.0197 (2)
S2	0.42025 (8)	0.92886 (7)	0.61200 (4)	0.0196 (2)
O1	0.6436 (2)	0.8879 (2)	0.90039 (13)	0.0290 (5)
O2	0.6126 (2)	1.1054 (2)	0.83495 (12)	0.0258 (5)
O3	0.0104 (2)	0.1626 (2)	0.26378 (12)	0.0222 (5)
O4	−0.0238 (2)	0.3735 (2)	0.19133 (13)	0.0273 (5)
C1	0.3073 (3)	0.7294 (3)	0.51711 (17)	0.0180 (6)
C2	0.4771 (3)	0.8283 (3)	0.71229 (17)	0.0198 (7)
C3	0.4109 (3)	0.6525 (3)	0.67430 (17)	0.0179 (6)
C4	0.3115 (3)	0.5931 (3)	0.55924 (17)	0.0167 (6)
C5	0.2161 (3)	0.4277 (3)	0.47680 (17)	0.0173 (6)
C6	0.1453 (3)	0.4496 (3)	0.37738 (18)	0.0187 (6)
C7	0.4314 (3)	0.5352 (3)	0.74333 (19)	0.0241 (7)
C8	0.2012 (3)	0.2576 (3)	0.49704 (18)	0.0215 (7)
C9	0.5860 (3)	0.9392 (3)	0.82492 (18)	0.0208 (7)
C10	0.7119 (4)	1.2220 (3)	0.94621 (19)	0.0270 (8)
C11	0.7189 (4)	1.3989 (3)	0.9461 (2)	0.0333 (8)
C12	0.0360 (3)	0.3267 (3)	0.26830 (18)	0.0200 (7)
C13	−0.0980 (3)	0.0358 (3)	0.15737 (18)	0.0238 (7)
C14	−0.1327 (4)	−0.1397 (3)	0.1742 (2)	0.0339 (8)
H7A	0.51440	0.60450	0.81710	0.0360*
H7B	0.49260	0.45630	0.70920	0.0360*
H7C	0.30070	0.46780	0.74890	0.0360*
H8A	0.09500	0.16430	0.43900	0.0320*
H8B	0.17240	0.25770	0.56880	0.0320*
H8C	0.32650	0.23930	0.49660	0.0320*
H10A	0.84740	1.22180	0.96810	0.0320*
H10B	0.63870	1.18320	0.99940	0.0320*
H11A	0.79250	1.43660	0.89370	0.0500*
H11B	0.78470	1.47890	1.02010	0.0500*
H11C	0.58420	1.39800	0.92450	0.0500*
H13A	−0.02020	0.05130	0.10210	0.0290*
H13B	−0.22530	0.04930	0.13110	0.0290*
H14A	−0.00580	−0.14950	0.20290	0.0510*
H14B	−0.20110	−0.22920	0.10380	0.0510*
H14C	−0.21400	−0.15490	0.22700	0.0510*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0227 (3)	0.0181 (3)	0.0164 (3)	0.0062 (2)	0.0022 (2)	0.0049 (2)
S2	0.0231 (3)	0.0171 (3)	0.0170 (3)	0.0065 (2)	0.0030 (2)	0.0041 (2)
O1	0.0353 (9)	0.0283 (10)	0.0183 (8)	0.0094 (8)	−0.0007 (7)	0.0051 (7)
O2	0.0300 (9)	0.0246 (10)	0.0164 (8)	0.0088 (7)	−0.0017 (7)	0.0003 (7)
O3	0.0253 (8)	0.0173 (9)	0.0181 (8)	0.0045 (7)	0.0002 (6)	0.0020 (6)
O4	0.0327 (9)	0.0233 (10)	0.0199 (8)	0.0064 (7)	−0.0002 (7)	0.0045 (7)
C1	0.0162 (10)	0.0191 (12)	0.0167 (10)	0.0050 (9)	0.0030 (8)	0.0037 (9)
C2	0.0196 (11)	0.0256 (13)	0.0152 (10)	0.0092 (9)	0.0043 (8)	0.0063 (9)
C3	0.0156 (10)	0.0218 (12)	0.0186 (11)	0.0074 (9)	0.0055 (8)	0.0083 (9)
C4	0.0130 (10)	0.0188 (12)	0.0187 (10)	0.0050 (8)	0.0053 (8)	0.0063 (9)
C5	0.0157 (10)	0.0173 (12)	0.0201 (11)	0.0065 (9)	0.0059 (8)	0.0061 (9)
C6	0.0171 (10)	0.0175 (12)	0.0199 (11)	0.0054 (9)	0.0048 (8)	0.0033 (9)
C7	0.0279 (12)	0.0230 (13)	0.0210 (11)	0.0095 (10)	0.0029 (9)	0.0074 (10)
C8	0.0225 (11)	0.0188 (12)	0.0218 (11)	0.0063 (9)	0.0035 (9)	0.0063 (9)
C9	0.0164 (11)	0.0251 (13)	0.0203 (11)	0.0071 (9)	0.0053 (9)	0.0052 (9)
C10	0.0321 (13)	0.0239 (14)	0.0191 (12)	0.0081 (10)	0.0013 (10)	0.0010 (10)
C11	0.0400 (15)	0.0257 (15)	0.0266 (13)	0.0098 (12)	−0.0010 (11)	0.0023 (11)
C12	0.0172 (11)	0.0207 (12)	0.0200 (11)	0.0046 (9)	0.0058 (8)	0.0041 (9)
C13	0.0221 (11)	0.0187 (13)	0.0211 (11)	0.0023 (9)	0.0009 (9)	−0.0025 (9)
C14	0.0379 (15)	0.0217 (14)	0.0345 (15)	0.0076 (11)	0.0043 (11)	0.0012 (11)

Geometric parameters (Å, º) top

S1—C1	1.711 (2)	C10—C11	1.484 (4)
S1—C6	1.751 (3)	C13—C14	1.501 (4)
S2—C1	1.712 (2)	C7—H7A	0.9800
S2—C2	1.758 (2)	C7—H7B	0.9800
O1—C9	1.214 (3)	C7—H7C	0.9800
O2—C9	1.334 (3)	C8—H8A	0.9800
O2—C10	1.465 (3)	C8—H8B	0.9800
O3—C12	1.331 (3)	C8—H8C	0.9800
O3—C13	1.459 (3)	C10—H10A	0.9900
O4—C12	1.211 (3)	C10—H10B	0.9900
C1—C4	1.386 (3)	C11—H11A	0.9800
C2—C3	1.360 (3)	C11—H11B	0.9800
C2—C9	1.475 (3)	C11—H11C	0.9800
C3—C4	1.437 (3)	C13—H13A	0.9900
C3—C7	1.495 (3)	C13—H13B	0.9900
C4—C5	1.441 (3)	C14—H14A	0.9800
C5—C6	1.373 (3)	C14—H14B	0.9800
C5—C8	1.495 (4)	C14—H14C	0.9800
C6—C12	1.472 (3)

C1—S1—C6	89.57 (11)	C3—C7—H7C	109.00
C1—S2—C2	89.39 (11)	H7A—C7—H7B	109.00
C9—O2—C10	114.48 (17)	H7A—C7—H7C	109.00
C12—O3—C13	115.57 (17)	H7B—C7—H7C	109.00
S1—C1—S2	132.34 (15)	C5—C8—H8A	109.00
S1—C1—C4	113.81 (17)	C5—C8—H8B	109.00
S2—C1—C4	113.85 (16)	C5—C8—H8C	109.00
S2—C2—C3	113.92 (16)	H8A—C8—H8B	110.00
S2—C2—C9	118.18 (18)	H8A—C8—H8C	109.00
C3—C2—C9	127.9 (2)	H8B—C8—H8C	109.00
C2—C3—C4	111.0 (2)	O2—C10—H10A	110.00
C2—C3—C7	124.9 (2)	O2—C10—H10B	110.00
C4—C3—C7	124.1 (2)	C11—C10—H10A	110.00
C1—C4—C3	111.8 (2)	C11—C10—H10B	110.00
C1—C4—C5	112.16 (19)	H10A—C10—H10B	108.00
C3—C4—C5	136.0 (2)	C10—C11—H11A	109.00
C4—C5—C6	110.3 (2)	C10—C11—H11B	109.00
C4—C5—C8	124.45 (19)	C10—C11—H11C	109.00
C6—C5—C8	125.3 (2)	H11A—C11—H11B	109.00
S1—C6—C5	114.18 (18)	H11A—C11—H11C	109.00
S1—C6—C12	113.10 (17)	H11B—C11—H11C	109.00
C5—C6—C12	132.7 (2)	O3—C13—H13A	110.00
O1—C9—O2	123.4 (2)	O3—C13—H13B	110.00
O1—C9—C2	125.1 (2)	C14—C13—H13A	110.00
O2—C9—C2	111.59 (19)	C14—C13—H13B	110.00
O2—C10—C11	108.25 (19)	H13A—C13—H13B	109.00
O3—C12—O4	124.3 (2)	C13—C14—H14A	109.00
O3—C12—C6	113.56 (19)	C13—C14—H14B	109.00
O4—C12—C6	122.1 (2)	C13—C14—H14C	109.00
O3—C13—C14	106.76 (18)	H14A—C14—H14B	110.00
C3—C7—H7A	109.00	H14A—C14—H14C	109.00
C3—C7—H7B	109.00	H14B—C14—H14C	109.00

C6—S1—C1—S2	179.7 (2)	C9—C2—C3—C7	2.3 (4)
C6—S1—C1—C4	0.3 (2)	S2—C2—C9—O1	−175.95 (19)
C1—S1—C6—C5	−0.3 (2)	S2—C2—C9—O2	4.8 (3)
C1—S1—C6—C12	179.25 (18)	C3—C2—C9—O1	4.7 (4)
C2—S2—C1—S1	−179.2 (2)	C3—C2—C9—O2	−174.6 (2)
C2—S2—C1—C4	0.3 (2)	C2—C3—C4—C1	−0.5 (3)
C1—S2—C2—C3	−0.6 (2)	C2—C3—C4—C5	179.2 (3)
C1—S2—C2—C9	180.0 (2)	C7—C3—C4—C1	177.4 (2)
C10—O2—C9—O1	−2.0 (3)	C7—C3—C4—C5	−3.0 (4)
C10—O2—C9—C2	177.3 (2)	C1—C4—C5—C6	−0.1 (3)
C9—O2—C10—C11	−176.3 (2)	C1—C4—C5—C8	178.6 (2)
C13—O3—C12—O4	−0.1 (3)	C3—C4—C5—C6	−179.8 (3)
C13—O3—C12—C6	179.74 (19)	C3—C4—C5—C8	−1.0 (4)
C12—O3—C13—C14	−172.8 (2)	C4—C5—C6—S1	0.3 (3)
S1—C1—C4—C3	179.62 (17)	C4—C5—C6—C12	−179.2 (2)
S1—C1—C4—C5	−0.1 (3)	C8—C5—C6—S1	−178.41 (19)
S2—C1—C4—C3	0.1 (3)	C8—C5—C6—C12	2.1 (4)
S2—C1—C4—C5	−179.66 (17)	S1—C6—C12—O3	176.14 (16)
S2—C2—C3—C4	0.7 (3)	S1—C6—C12—O4	−4.0 (3)
S2—C2—C3—C7	−177.17 (19)	C5—C6—C12—O3	−4.4 (4)
C9—C2—C3—C4	−179.9 (2)	C5—C6—C12—O4	175.5 (3)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the S2/C1–C4 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O1	0.98	2.22	2.980 (3)	133
C8—H8A···O3	0.98	2.23	2.909 (3)	125
C11—H11A···O4ⁱ	0.98	2.53	3.471 (3)	161
C8—H8C···Cg2ⁱⁱ	0.98	2.74	3.578 (3)	144

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₆O₄S₂
M_r	312.39
Crystal system, space group	Triclinic, P1
Temperature (K)	123
a, b, c (Å)	7.3497 (3), 8.4720 (4), 12.8629 (5)
α, β, γ (°)	102.770 (3), 99.545 (3), 107.779 (4)
V (Å³)	719.96 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.38
Crystal size (mm)	0.30 × 0.08 × 0.06

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.966, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6901, 3486, 2661
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.692

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.106, 1.04
No. of reflections	3486
No. of parameters	185
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.34

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009), WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the S2/C1–C4 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O1	0.98	2.22	2.980 (3)	133
C8—H8A···O3	0.98	2.23	2.909 (3)	125
C11—H11A···O4ⁱ	0.98	2.53	3.471 (3)	161
C8—H8C···Cg2ⁱⁱ	0.98	2.74	3.578 (3)	144

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

Acknowledgements

SHHY thanks Sohag University for facilitating this collaborative project with Manchester Metropolitan University. Our gratitude is extended to Erciyes University and the University of Strathclyde for supporting this study.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Comel, A. & Kirsch, G. (2001a). J. Heterocycl. Chem. 38, 1167–1171. CAS Google Scholar
Comel, A. & Kirsch, G. (2001b). J. Heterocycl. Chem. 38, 1167–1171. CAS Google Scholar
Egbertson, M. S., Cook, J. J., Hednar, H., Prugh, J. D., Hednar, R. A., Gaul, S. L., Gould, R. J., Hartman, G. D., Homnick, C. F., Holahan, L. M. M., Libby, L. A., Lynch, J. J., Sitko, G. R., Stranieri, M. T. & Vassallo, L. M. (1999). J. Med. Chem. 42, 2409–2421. Web of Science CrossRef PubMed CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Gather, M. C., Heeny, M., Zhang, W., Whitehead, K. S., Bradley, D. D. C., McCulloch, I. & Campbell, A. J. (2008). Chem. Commun. 9, 1079–1081. Web of Science CrossRef Google Scholar
Gunasekaran, B., Sureshbabu, R., Mohanakrishnan, A. K., Chakkaravarthi, G. & Manivannan, V. (2009). Acta Cryst. E65, o2455. Web of Science CSD CrossRef IUCr Journals Google Scholar
He, M., Li, J., Sorensen, M. L., Zhang, F., Hancock, R. R., Fong, H. H., Pozdin, V. A., Smilgies, D. & Malliaras, G. G. (2009). J. Am. Chem. Soc. 131, 11930–11938. Web of Science CrossRef PubMed CAS Google Scholar
Heeney, M., Bailey, C., Genevicius, K., Shkunov, M., Sparrowe, D., Tierney, S. & McCulloch, U. (2005). J. Am. Chem. Soc. 127, 1078–1079. Web of Science CrossRef PubMed CAS Google Scholar
Jarak, I., Kralj, M., Piantanida, I., Suman, L., Zinic, M., Pavelic, K. & Karminski-Zamola, G. (2006). Bioorg. Med. Chem. 14, 2859–2868. Web of Science CrossRef PubMed CAS Google Scholar
Lee, K. & Sotzing, G. A. (2001). Macromolecules, 34, 5746–5747. Web of Science CrossRef CAS Google Scholar
Litvinov, V. P. (2005). Russ. Chem. Rev. 74, 217–248. CrossRef CAS Google Scholar
Mabkhot, N. Y., Barakat, A., Al-Majid, A. M. & Alshahrani, S. A. (2012). Int. J. Mol. Sci. 13, 2263–2275. Web of Science CrossRef CAS PubMed Google Scholar
Mabkhot, Y. N., Kheder, N. A. & Al-Majid, A. M. (2010). Molecules, 15, 9418–9426. Web of Science CrossRef CAS PubMed Google Scholar
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Umadevi, M., Sureshbabu, R., Mohanakrishnan, A. K., Chakkaravarthi, G. & Manivannan, V. (2009). Acta Cryst. E65, o2790. Web of Science CrossRef IUCr Journals Google Scholar
Wang, X., Li, Y. & Liu, M.-G. (2008). Acta Cryst. E64, o1180. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 12| December 2012| Pages o3332-o3333

doi:10.1107/S160053681204593X

Open

access