3,4-Di-methyl-thieno[2,3-b]thio-phene-2,5-dicarbo-nitrile.

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

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 = 218.31

Triclinic,

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[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.132

S = 0.99

4912 reflections

257 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813017960/rz5077sup1.cif

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813017960/rz5077Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H6N2S2	Z = 4
Mr = 218.31	F(000) = 448
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0565P)2] where P = (Fo2 + 2Fc2)/3
4912 reflections	(Δ/σ)max = 0.001
257 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)