3,4-Di­methyl­thieno[2,3-b]thio­phene-2,5-dicarbo­nitrile

Mabkhot, Y.N.; Al-Showiman, S.S.; Barakat, A.; Choudhary, M.I.; Yousuf, S.

doi:10.1107/S1600536813017960

organic compounds

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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Page o1272

doi:10.1107/S1600536813017960

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3,4-Dimethylthieno[2,3-b]thiophene-2,5-dicarbonitrile

Yahia Nasser Mabkhot,^a ‡ S. S. Al-Showiman,^a Assem Barakat,^a,^b M. Iqbal Choudhary ^c,^a and Sammer Yousuf ^c ^*

^aDepartment of Chemistry, College of Science, King Saud University, PO Box 2455, Riyadh 11451, Saudi Arabia, ^bDepartment of Chemistry, Faculty of Science, Alexandria University, PO Box 426, Ibrahimia- 21321 Alexandria, Egypt, and ^cH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
^*Correspondence e-mail: dr.sammer.yousuf@gmail.com

(Received 24 June 2013; accepted 29 June 2013; online 17 July 2013)

The asymmetric unit of the title compound, C₁₀H₆N₂S₂, contains two crystallographically independent but conformationally similar molecules. The fused thiophene ring cores are almost planar [maximum deviation = 0.027 (3) Å] with the thiophene rings forming dihedral angles of 0.5 (4)° in one molecule and 1.91 (4)° in the other. The crystal packing is stabilized only by van der Waals interactions.

Related literature

For the biological activity of thiophene derivatives, see: Mabkhot et al. (2013 ); Mishra et al. (2011 ). For the synthesis of fused heterocyclic compounds, see: Cornel & Kirsch (2001 ); Mashraqui et al. (1999 ). For crystal data for related thiophene compounds, see: Gunasekaran et al. (2009 ); Mashraqui et al. (2004 ).

Experimental

Crystal data

C₁₀H₆N₂S₂
M_r = 218.31
Triclinic, $[P \overline 1]$
a = 7.2573 (11) Å
b = 10.1538 (15) Å
c = 13.665 (2) Å
α = 94.467 (3)°
β = 99.120 (4)°
γ = 95.850 (4)°
V = 984.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.50 mm⁻¹
T = 273 K
0.37 × 0.15 × 0.11 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.838, T_max = 0.947
13821 measured reflections
4912 independent reflections
3074 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.132
S = 0.99
4912 reflections
257 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813017960/rz5077sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813017960/rz5077Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813017960/rz5077Isup3.cml

checkCIF report

Comment top

Thiophene moieties containing heterocyclic compounds are known to have a number of biological activities, including anti-inflammatory, anti-oxidant and anti-glycation properties etc. (Mabkhot et al., 2013; Mishra et al. 2011). The title compound is a thiophene derivative, composed of two fused thiophene rings. It was synthesized as part of our ongoing research towards the synthesis of novel chemical entities with diverse biological activities.

The title, compound C₁₀H₆N₂S₂, contains two independent (S1–S2/C1–C6 and S3–S4/C11–C16) in the asymmetric unit (Fig. 1). Structurally it is similar to the previous reported compound diethyl 3,4-bis(acetoxymethyl)thieno-[2,3-b]thiophene-2,5-dicarboxylate (Gunasekaran et al., 2009) with the difference that four acetoxy methyl substituents has been replaced by two nitrile and two methyl substituents. The fused thiophene ring cores are almost planar [maximum deviation 0.027 (3) Å for atom C16] as indicated by the dihedral angles formed by the thiophene rings of 0.5 (4)° in one molecule and 1.91 (4)° in the other. The crystal packing (Fig. 2) is stabilized only by van der Waals interactions.

Related literature top

For the biological activity of thiophene derivatives, see: Mabkhot et al. (2013); Mishra et al. (2011). For the synthesis of fused heterocyclic compounds, see: Cornel et al. (2001); Mashraqui et al. (1999). For crystal data for related thiophene compounds, see: Gunasekaran et al. (2009); Mashraqui et al. (2004).

Experimental top

The title compound was synthesized by following the procedure described in the literature (Mashraqui et al., 1999; Cornel et al., 2001). The compound was crystallized by using a mixture of dimethyl formamide (DMF) and dichloromethane (CH₂Cl₂) (1:1 v/v) at room temperature to obtain light brown crystals. M. p. 498 K. Anal. calcd. for C₁₀H₆N₂S₂: C, 55.04; H, 2.75; N, 12.84. Found: C, 54.82; H, 2.92; N, 12.97.

Spectral Data: IR (KBr, cm^-1): 2964, 2213 cm-1; ¹H-NMR (400 MHz, CDCl₃): δ 2.69 (s, 6H, CH₃); ¹³C-NMR (100 MHz, CDCl₃): δ 14.8 (2 CH₃), 108.5 (2 CAr), 113.3 (2 CN), 134.1 (CAr), 143.1 (2 CAr), 150.8 p.p.m. (CAr).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Partial packing diagram of the title compound. Hydrogen atoms are omitted for clarity.

3,4-Dimethylthieno[2,3-b]thiophene-2,5-dicarbonitrile top

Crystal data top

C₁₀H₆N₂S₂	Z = 4
M_r = 218.31	F(000) = 448
Triclinic, P1	D_x = 1.473 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2573 (11) Å	Cell parameters from 1631 reflections
b = 10.1538 (15) Å	θ = 1.5–28.4°
c = 13.665 (2) Å	µ = 0.50 mm⁻¹
α = 94.467 (3)°	T = 273 K
β = 99.120 (4)°	Block, brown
γ = 95.850 (4)°	0.37 × 0.15 × 0.11 mm
V = 984.5 (3) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4912 independent reflections
Radiation source: fine-focus sealed tube	3074 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
ω scan	θ_max = 28.4°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→9
T_min = 0.838, T_max = 0.947	k = −13→13
13821 measured reflections	l = −18→18

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.132	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0565P)²] where P = (F_o² + 2F_c²)/3
4912 reflections	(Δ/σ)_max = 0.001
257 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₀H₆N₂S₂	γ = 95.850 (4)°
M_r = 218.31	V = 984.5 (3) Å³
Triclinic, P1	Z = 4
a = 7.2573 (11) Å	Mo Kα radiation
b = 10.1538 (15) Å	µ = 0.50 mm⁻¹
c = 13.665 (2) Å	T = 273 K
α = 94.467 (3)°	0.37 × 0.15 × 0.11 mm
β = 99.120 (4)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4912 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	3074 reflections with I > 2σ(I)
T_min = 0.838, T_max = 0.947	R_int = 0.053
13821 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.132	H-atom parameters constrained
S = 0.99	Δρ_max = 0.37 e Å⁻³
4912 reflections	Δρ_min = −0.24 e Å⁻³
257 parameters

Special details top

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	0.18703 (11)	0.32325 (7)	0.83846 (5)	0.0460 (2)
S2	0.24419 (10)	0.62763 (7)	0.91346 (5)	0.0435 (2)
S3	0.38935 (11)	1.16617 (7)	0.61752 (6)	0.0477 (2)
S4	0.37946 (11)	0.89010 (8)	0.70279 (5)	0.0473 (2)
N1	0.1667 (4)	−0.0317 (3)	0.8989 (2)	0.0718 (9)
N2	0.3550 (4)	0.8848 (3)	1.1405 (2)	0.0706 (9)
N3	0.2705 (5)	1.3690 (3)	0.4034 (3)	0.0902 (11)
N4	0.2415 (4)	0.5277 (3)	0.6753 (2)	0.0827 (10)
C1	0.1990 (4)	0.2211 (3)	0.9361 (2)	0.0424 (7)
C2	0.2290 (4)	0.2874 (3)	1.0280 (2)	0.0381 (6)
C3	0.2441 (3)	0.4276 (2)	1.02172 (19)	0.0336 (6)
C4	0.2755 (4)	0.5432 (3)	1.0910 (2)	0.0384 (6)
C5	0.2804 (4)	0.6552 (3)	1.0431 (2)	0.0396 (7)
C6	0.2251 (4)	0.4597 (3)	0.9243 (2)	0.0371 (6)
C7	0.1799 (4)	0.0807 (3)	0.9144 (2)	0.0520 (8)
C8	0.2489 (4)	0.2224 (3)	1.1236 (2)	0.0471 (7)
H8A	0.2582	0.1294	1.1097	0.071*
H8B	0.1410	0.2332	1.1547	0.071*
H8C	0.3601	0.2632	1.1674	0.071*
C9	0.3013 (4)	0.5424 (3)	1.20166 (19)	0.0447 (7)
H9A	0.3111	0.6320	1.2319	0.067*
H9B	0.4138	0.5039	1.2246	0.067*
H9C	0.1954	0.4909	1.2196	0.067*
C10	0.3195 (4)	0.7857 (3)	1.0941 (2)	0.0474 (7)
C11	0.2885 (4)	1.1564 (3)	0.4924 (2)	0.0457 (7)
C12	0.2220 (4)	1.0317 (3)	0.4497 (2)	0.0410 (7)
C13	0.2546 (3)	0.9366 (3)	0.52151 (18)	0.0341 (6)
C14	0.2139 (4)	0.7963 (3)	0.5223 (2)	0.0389 (6)
C15	0.2732 (4)	0.7597 (3)	0.6151 (2)	0.0441 (7)
C16	0.3434 (4)	0.9965 (3)	0.6131 (2)	0.0378 (6)
C17	0.2795 (5)	1.2748 (3)	0.4434 (3)	0.0590 (9)
C18	0.1286 (4)	0.9979 (3)	0.34337 (19)	0.0452 (7)
H18A	0.1082	1.0783	0.3128	0.068*
H18B	0.0102	0.9451	0.3412	0.068*
H18C	0.2077	0.9486	0.3081	0.068*
C19	0.1235 (4)	0.6996 (3)	0.4357 (2)	0.0453 (7)
H19A	0.1213	0.6108	0.4554	0.068*
H19B	0.1938	0.7076	0.3822	0.068*
H19C	−0.0028	0.7184	0.4140	0.068*
C20	0.2548 (4)	0.6297 (3)	0.6466 (2)	0.0546 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0602 (5)	0.0394 (4)	0.0360 (4)	0.0018 (3)	0.0067 (3)	−0.0035 (3)
S2	0.0552 (5)	0.0359 (4)	0.0397 (4)	0.0042 (3)	0.0079 (3)	0.0063 (3)
S3	0.0538 (5)	0.0395 (4)	0.0488 (5)	0.0045 (3)	0.0102 (4)	−0.0032 (3)
S4	0.0534 (5)	0.0508 (5)	0.0343 (4)	0.0019 (4)	0.0001 (3)	0.0040 (3)
N1	0.100 (2)	0.0396 (16)	0.075 (2)	−0.0008 (16)	0.0267 (18)	−0.0085 (15)
N2	0.096 (2)	0.0385 (16)	0.074 (2)	0.0009 (15)	0.0168 (18)	−0.0122 (15)
N3	0.126 (3)	0.067 (2)	0.096 (3)	0.034 (2)	0.044 (2)	0.036 (2)
N4	0.094 (2)	0.059 (2)	0.083 (2)	−0.0117 (17)	−0.0187 (18)	0.0285 (18)
C1	0.0446 (16)	0.0374 (16)	0.0437 (17)	0.0029 (13)	0.0064 (13)	−0.0007 (13)
C2	0.0362 (15)	0.0378 (15)	0.0390 (16)	0.0041 (12)	0.0023 (12)	0.0039 (13)
C3	0.0340 (14)	0.0327 (14)	0.0331 (15)	0.0031 (11)	0.0038 (11)	0.0025 (12)
C4	0.0351 (15)	0.0411 (16)	0.0375 (16)	0.0034 (12)	0.0030 (12)	0.0016 (13)
C5	0.0426 (16)	0.0355 (15)	0.0387 (16)	0.0024 (12)	0.0038 (13)	−0.0002 (13)
C6	0.0396 (15)	0.0341 (15)	0.0364 (16)	0.0044 (12)	0.0046 (12)	−0.0001 (12)
C7	0.063 (2)	0.0372 (17)	0.055 (2)	0.0003 (15)	0.0145 (16)	−0.0051 (15)
C8	0.0604 (19)	0.0353 (16)	0.0450 (18)	0.0048 (14)	0.0022 (14)	0.0143 (14)
C9	0.0579 (18)	0.0425 (16)	0.0303 (15)	0.0027 (14)	0.0015 (13)	−0.0020 (13)
C10	0.0543 (18)	0.0351 (16)	0.0538 (19)	0.0085 (14)	0.0114 (15)	0.0007 (15)
C11	0.0480 (17)	0.0458 (18)	0.0489 (18)	0.0131 (14)	0.0175 (14)	0.0102 (15)
C12	0.0351 (15)	0.0507 (18)	0.0424 (17)	0.0122 (13)	0.0152 (13)	0.0097 (14)
C13	0.0290 (13)	0.0421 (16)	0.0314 (15)	0.0047 (12)	0.0072 (11)	0.0005 (12)
C14	0.0345 (14)	0.0447 (17)	0.0368 (16)	0.0044 (12)	0.0060 (12)	0.0004 (13)
C15	0.0454 (16)	0.0437 (17)	0.0422 (17)	0.0028 (13)	0.0050 (13)	0.0048 (14)
C16	0.0367 (15)	0.0398 (15)	0.0370 (16)	0.0055 (12)	0.0077 (12)	−0.0003 (12)
C17	0.070 (2)	0.050 (2)	0.067 (2)	0.0178 (17)	0.0297 (19)	0.0122 (18)
C18	0.0427 (16)	0.063 (2)	0.0307 (15)	0.0129 (14)	0.0007 (13)	0.0102 (14)
C19	0.0459 (17)	0.0402 (16)	0.0440 (17)	−0.0025 (13)	0.0009 (13)	−0.0084 (13)
C20	0.057 (2)	0.050 (2)	0.052 (2)	−0.0026 (16)	−0.0051 (15)	0.0129 (16)

Geometric parameters (Å, º) top

S1—C6	1.714 (3)	C8—H8A	0.9600
S1—C1	1.750 (3)	C8—H8B	0.9600
S2—C6	1.716 (3)	C8—H8C	0.9600
S2—C5	1.745 (3)	C9—H9A	0.9600
S3—C16	1.716 (3)	C9—H9B	0.9600
S3—C11	1.741 (3)	C9—H9C	0.9600
S4—C16	1.703 (3)	C11—C12	1.360 (4)
S4—C15	1.742 (3)	C11—C17	1.423 (4)
N1—C7	1.136 (4)	C12—C13	1.439 (3)
N2—C10	1.130 (4)	C12—C18	1.501 (4)
N3—C17	1.140 (4)	C13—C16	1.377 (3)
N4—C20	1.137 (4)	C13—C14	1.427 (4)
C1—C2	1.351 (4)	C14—C15	1.365 (4)
C1—C7	1.421 (4)	C14—C19	1.495 (4)
C2—C3	1.428 (3)	C15—C20	1.420 (4)
C2—C8	1.502 (4)	C18—H18A	0.9600
C3—C6	1.384 (3)	C18—H18B	0.9600
C3—C4	1.425 (4)	C18—H18C	0.9600
C4—C5	1.356 (4)	C19—H19A	0.9600
C4—C9	1.495 (4)	C19—H19B	0.9600
C5—C10	1.428 (4)	C19—H19C	0.9600

C6—S1—C1	89.13 (13)	H9B—C9—H9C	109.5
C6—S2—C5	88.80 (13)	N2—C10—C5	175.0 (4)
C16—S3—C11	88.88 (14)	C12—C11—C17	125.3 (3)
C16—S4—C15	88.73 (13)	C12—C11—S3	115.1 (2)
C2—C1—C7	126.0 (3)	C17—C11—S3	119.6 (2)
C2—C1—S1	114.5 (2)	C11—C12—C13	110.0 (3)
C7—C1—S1	119.5 (2)	C11—C12—C18	125.1 (3)
C1—C2—C3	110.7 (2)	C13—C12—C18	124.9 (3)
C1—C2—C8	124.6 (3)	C16—C13—C14	111.9 (2)
C3—C2—C8	124.6 (2)	C16—C13—C12	112.0 (2)
C6—C3—C4	111.9 (2)	C14—C13—C12	136.0 (3)
C6—C3—C2	112.3 (2)	C15—C14—C13	110.0 (2)
C4—C3—C2	135.9 (2)	C15—C14—C19	123.4 (3)
C5—C4—C3	110.8 (2)	C13—C14—C19	126.5 (3)
C5—C4—C9	124.2 (3)	C14—C15—C20	127.2 (3)
C3—C4—C9	125.0 (2)	C14—C15—S4	114.8 (2)
C4—C5—C10	123.0 (3)	C20—C15—S4	118.0 (2)
C4—C5—S2	114.7 (2)	C13—C16—S4	114.5 (2)
C10—C5—S2	122.2 (2)	C13—C16—S3	114.0 (2)
C3—C6—S1	113.3 (2)	S4—C16—S3	131.48 (17)
C3—C6—S2	113.8 (2)	N3—C17—C11	179.2 (4)
S1—C6—S2	132.84 (17)	C12—C18—H18A	109.5
N1—C7—C1	178.6 (4)	C12—C18—H18B	109.5
C2—C8—H8A	109.5	H18A—C18—H18B	109.5
C2—C8—H8B	109.5	C12—C18—H18C	109.5
H8A—C8—H8B	109.5	H18A—C18—H18C	109.5
C2—C8—H8C	109.5	H18B—C18—H18C	109.5
H8A—C8—H8C	109.5	C14—C19—H19A	109.5
H8B—C8—H8C	109.5	C14—C19—H19B	109.5
C4—C9—H9A	109.5	H19A—C19—H19B	109.5
C4—C9—H9B	109.5	C14—C19—H19C	109.5
H9A—C9—H9B	109.5	H19A—C19—H19C	109.5
C4—C9—H9C	109.5	H19B—C19—H19C	109.5
H9A—C9—H9C	109.5	N4—C20—C15	177.4 (4)

C6—S1—C1—C2	0.4 (2)	C16—S3—C11—C12	0.6 (2)
C6—S1—C1—C7	−178.9 (2)	C16—S3—C11—C17	180.0 (2)
C7—C1—C2—C3	179.1 (3)	C17—C11—C12—C13	−179.8 (3)
S1—C1—C2—C3	−0.1 (3)	S3—C11—C12—C13	−0.4 (3)
C7—C1—C2—C8	0.5 (5)	C17—C11—C12—C18	0.3 (5)
S1—C1—C2—C8	−178.6 (2)	S3—C11—C12—C18	179.7 (2)
C1—C2—C3—C6	−0.3 (3)	C11—C12—C13—C16	0.0 (3)
C8—C2—C3—C6	178.3 (2)	C18—C12—C13—C16	179.8 (2)
C1—C2—C3—C4	−179.5 (3)	C11—C12—C13—C14	178.1 (3)
C8—C2—C3—C4	−1.0 (5)	C18—C12—C13—C14	−2.0 (5)
C6—C3—C4—C5	−0.6 (3)	C16—C13—C14—C15	0.6 (3)
C2—C3—C4—C5	178.7 (3)	C12—C13—C14—C15	−177.5 (3)
C6—C3—C4—C9	179.9 (2)	C16—C13—C14—C19	−178.2 (2)
C2—C3—C4—C9	−0.9 (5)	C12—C13—C14—C19	3.7 (5)
C3—C4—C5—C10	−176.6 (3)	C13—C14—C15—C20	178.6 (3)
C9—C4—C5—C10	3.0 (4)	C19—C14—C15—C20	−2.5 (5)
C3—C4—C5—S2	0.9 (3)	C13—C14—C15—S4	−0.4 (3)
C9—C4—C5—S2	−179.5 (2)	C19—C14—C15—S4	178.5 (2)
C6—S2—C5—C4	−0.8 (2)	C16—S4—C15—C14	0.1 (2)
C6—S2—C5—C10	176.8 (3)	C16—S4—C15—C20	−179.0 (2)
C4—C3—C6—S1	180.00 (18)	C14—C13—C16—S4	−0.6 (3)
C2—C3—C6—S1	0.5 (3)	C12—C13—C16—S4	177.97 (17)
C4—C3—C6—S2	0.0 (3)	C14—C13—C16—S3	−178.12 (18)
C2—C3—C6—S2	−179.51 (18)	C12—C13—C16—S3	0.5 (3)
C1—S1—C6—C3	−0.5 (2)	C15—S4—C16—C13	0.3 (2)
C1—S1—C6—S2	179.6 (2)	C15—S4—C16—S3	177.3 (2)
C5—S2—C6—C3	0.5 (2)	C11—S3—C16—C13	−0.6 (2)
C5—S2—C6—S1	−179.6 (2)	C11—S3—C16—S4	−177.5 (2)

Experimental details

Crystal data
Chemical formula	C₁₀H₆N₂S₂
M_r	218.31
Crystal system, space group	Triclinic, P1
Temperature (K)	273
a, b, c (Å)	7.2573 (11), 10.1538 (15), 13.665 (2)
α, β, γ (°)	94.467 (3), 99.120 (4), 95.850 (4)
V (Å³)	984.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.50
Crystal size (mm)	0.37 × 0.15 × 0.11

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.838, 0.947
No. of measured, independent and observed [I > 2σ(I)] reflections	13821, 4912, 3074
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.132, 0.99
No. of reflections	4912
No. of parameters	257
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.24

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Footnotes

‡Additional correspondence author, e-mail: yahia@ksu.edu.sa.

Acknowledgements

The authors extend their appreciation to the Deanship of Scientific Research at the King Saud University (Riyadh) for funding this study through the research grant No. RGP-VPP-007.

References

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