2-[5-(Benzo[d]thia-zol-2-yl)thio-phen-2-yl]benzo[d]thia-zole.

The structure of the title compound, C(18)H(10)N(2)S(3), consists of a central thio-phene ring and two terminal thia-zole rings. The two S atoms of the thia-zole rings are trans to the thio-phene S atom sulfur. The thia-zole rings are approximately coplanar with the thio-phene ring, with dihedral angles of 6.23 (11) and 4.81 (11)° between them. In the crystal, zigzag chains are formed along [010] by weak C-H⋯N inter-actions.

Related literature

For the synthesis of thio­phene derivatives, see: Kaleta et al. (2006 ▶); Minetto et al. (2005 ▶); Bayh et al. (2005 ▶). For their conformation, see: Alberti et al. (1986 ▶); Hagen (1986 ▶); Salman (1982 ▶) and for their applications, see: Seed et al. (2003 ▶); Cheylan et al. (2006 ▶); Karimian (2009 ▶); Kiryanov et al. (2001 ▶); Shi et al. (1996 ▶).

Experimental

Crystal data

C18H10N2S3

M = 350.48

Monoclinic,

a = 15.7297 (14) Å

b = 8.2396 (5) Å

c = 12.8160 (12) Å

β = 112.872 (11)°

V = 1530.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.48 mm−1

T = 200 K

0.34 × 0.15 × 0.01 mm

Data collection

Oxford XCalibur diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.839, T max = 1.000

5789 measured reflections

3086 independent reflections

1452 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.051

S = 0.72

3086 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.30 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶) and PARST (Nardelli, 1995 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810004009/ez2199sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810004009/ez2199Isup2.hkl

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

C18H10N2S3	F(000) = 720
Mr = 350.48	Dx = 1.521 (1) Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.7297 (14) Å	Cell parameters from 1275 reflections
b = 8.2396 (5) Å	θ = 4.2–26.2°
c = 12.8160 (12) Å	µ = 0.48 mm−1
β = 112.872 (11)°	T = 200 K
V = 1530.4 (2) Å3	Needles, yellow
Z = 4	0.34 × 0.15 × 0.01 mm

Oxford XCalibur diffractometer	3086 independent reflections
Radiation source: fine-focus sealed tube	1452 reflections with I > 2σ(I)
graphite	Rint = 0.053
Detector resolution: 15.9809 pixels mm-1	θmax = 26.3°, θmin = 4.2°
ω scans	h = −19→19
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −9→10
Tmin = 0.839, Tmax = 1.000	l = −9→15
5789 measured reflections

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.051	H-atom parameters constrained
S = 0.72	w = 1/[σ2(Fo2) + (0.006P)2] where P = (Fo2 + 2Fc2)/3
3086 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

	x	y	z	Uiso*/Ueq
S1	0.19188 (5)	−0.01268 (9)	0.55789 (7)	0.0372 (2)
S2	0.40390 (5)	0.14749 (8)	0.43819 (7)	0.0294 (2)
S3	0.65397 (5)	0.41064 (8)	0.64495 (7)	0.0351 (2)
N1	0.22730 (15)	−0.0478 (2)	0.3780 (2)	0.0306 (7)
N2	0.57525 (15)	0.3239 (2)	0.4337 (2)	0.0258 (6)
C1	0.11335 (19)	−0.1200 (3)	0.4461 (3)	0.0294 (8)
C2	0.1446 (2)	−0.1266 (3)	0.3573 (3)	0.0299 (8)
C3	0.0918 (2)	−0.2090 (3)	0.2584 (3)	0.0393 (9)
H3	0.1119	−0.2156	0.1975	0.047*
C4	0.0108 (2)	−0.2802 (3)	0.2499 (3)	0.0421 (9)
H4	−0.0250	−0.3369	0.1825	0.051*
C5	−0.0200 (2)	−0.2717 (3)	0.3369 (3)	0.0436 (9)
H5	−0.0766	−0.3220	0.3284	0.052*
C6	0.0300 (2)	−0.1917 (3)	0.4350 (3)	0.0383 (9)
H6	0.0084	−0.1851	0.4946	0.046*
C7	0.25959 (18)	0.0157 (3)	0.4775 (3)	0.0252 (7)
C8	0.34453 (18)	0.1056 (3)	0.5237 (3)	0.0233 (7)
C9	0.38812 (19)	0.1676 (3)	0.6290 (3)	0.0321 (8)
H9	0.3656	0.1568	0.6875	0.039*
C10	0.46999 (19)	0.2493 (3)	0.6426 (2)	0.0292 (8)
H10	0.5091	0.2988	0.7115	0.035*
C11	0.48737 (18)	0.2503 (3)	0.5468 (2)	0.0242 (7)
C12	0.56531 (19)	0.3212 (3)	0.5304 (3)	0.0252 (8)
C13	0.70982 (19)	0.4587 (3)	0.5569 (3)	0.0278 (8)
C14	0.6576 (2)	0.4025 (3)	0.4477 (3)	0.0280 (8)
C15	0.6891 (2)	0.4295 (3)	0.3612 (3)	0.0372 (8)
H15	0.6546	0.3929	0.2862	0.045*
C16	0.7711 (2)	0.5105 (3)	0.3873 (3)	0.0401 (9)
H16	0.7925	0.5313	0.3287	0.048*
C17	0.8235 (2)	0.5627 (3)	0.4957 (3)	0.0392 (9)
H17	0.8806	0.6163	0.5109	0.047*
C18	0.79350 (19)	0.5377 (3)	0.5819 (3)	0.0370 (9)
H18	0.8291	0.5735	0.6567	0.044*

	U11	U22	U33	U12	U13	U23
S1	0.0338 (5)	0.0475 (5)	0.0327 (6)	−0.0084 (4)	0.0156 (4)	−0.0013 (4)
S2	0.0278 (4)	0.0338 (4)	0.0285 (5)	−0.0019 (4)	0.0131 (4)	−0.0010 (4)
S3	0.0355 (5)	0.0414 (5)	0.0292 (6)	−0.0081 (4)	0.0136 (4)	−0.0030 (4)
N1	0.0267 (16)	0.0288 (16)	0.039 (2)	−0.0070 (12)	0.0154 (14)	−0.0019 (12)
N2	0.0235 (14)	0.0293 (14)	0.0270 (18)	−0.0032 (12)	0.0124 (13)	0.0000 (12)
C1	0.0301 (18)	0.0262 (18)	0.031 (2)	0.0001 (15)	0.0110 (16)	0.0036 (14)
C2	0.0319 (19)	0.0250 (18)	0.031 (2)	0.0034 (15)	0.0107 (17)	0.0043 (15)
C3	0.046 (2)	0.045 (2)	0.032 (2)	−0.0112 (17)	0.0211 (19)	−0.0050 (17)
C4	0.037 (2)	0.047 (2)	0.037 (3)	−0.0182 (17)	0.0080 (19)	−0.0047 (17)
C5	0.035 (2)	0.048 (2)	0.048 (3)	−0.0127 (17)	0.016 (2)	0.0046 (19)
C6	0.033 (2)	0.046 (2)	0.039 (3)	−0.0050 (17)	0.0173 (19)	0.0065 (18)
C7	0.0272 (19)	0.0201 (16)	0.031 (2)	0.0017 (15)	0.0142 (17)	0.0023 (16)
C8	0.0214 (17)	0.0226 (16)	0.028 (2)	−0.0018 (14)	0.0125 (16)	0.0004 (15)
C9	0.0338 (19)	0.0379 (18)	0.030 (2)	−0.0021 (15)	0.0182 (18)	0.0067 (16)
C10	0.0250 (18)	0.0350 (18)	0.025 (2)	−0.0007 (15)	0.0066 (16)	−0.0008 (15)
C11	0.0260 (18)	0.0194 (16)	0.025 (2)	0.0006 (14)	0.0079 (17)	0.0001 (14)
C12	0.0295 (19)	0.0170 (16)	0.029 (2)	0.0018 (14)	0.0107 (17)	0.0010 (14)
C13	0.0241 (18)	0.0270 (18)	0.036 (2)	0.0003 (14)	0.0154 (17)	0.0032 (15)
C14	0.0318 (19)	0.0253 (17)	0.029 (2)	0.0035 (15)	0.0148 (17)	0.0016 (15)
C15	0.045 (2)	0.0423 (19)	0.029 (2)	−0.0049 (17)	0.0191 (18)	−0.0056 (16)
C16	0.041 (2)	0.0410 (19)	0.051 (3)	−0.0025 (17)	0.033 (2)	0.0007 (19)
C17	0.031 (2)	0.0324 (18)	0.056 (3)	−0.0053 (16)	0.020 (2)	−0.0017 (18)
C18	0.0306 (19)	0.039 (2)	0.033 (2)	−0.0048 (15)	0.0033 (17)	−0.0002 (16)

S1—C1	1.728 (3)	C6—H6	0.9500
S1—C7	1.761 (3)	C7—C8	1.438 (3)
S2—C11	1.720 (3)	C8—C9	1.353 (3)
S2—C8	1.729 (3)	C9—C10	1.403 (3)
S3—C13	1.725 (3)	C9—H9	0.9500
S3—C12	1.747 (3)	C10—C11	1.357 (3)
N1—C7	1.286 (3)	C10—H10	0.9500
N1—C2	1.384 (3)	C11—C12	1.445 (3)
N2—C12	1.308 (3)	C13—C18	1.389 (3)
N2—C14	1.397 (3)	C13—C14	1.398 (4)
C1—C6	1.394 (3)	C14—C15	1.396 (4)
C1—C2	1.404 (4)	C15—C16	1.374 (3)
C2—C3	1.392 (3)	C15—H15	0.9500
C3—C4	1.368 (4)	C16—C17	1.380 (4)
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.379 (4)	C17—C18	1.375 (4)
C4—H4	0.9500	C17—H17	0.9500
C5—C6	1.366 (4)	C18—H18	0.9500
C5—H5	0.9500
?···?	?
C1—S1—C7	89.01 (14)	C8—C9—H9	123.5
C11—S2—C8	90.91 (14)	C10—C9—H9	123.5
C13—S3—C12	89.42 (14)	C11—C10—C9	112.8 (3)
C7—N1—C2	111.1 (3)	C11—C10—H10	123.6
C12—N2—C14	109.4 (2)	C9—C10—H10	123.6
C6—C1—C2	120.8 (3)	C10—C11—C12	127.9 (3)
C6—C1—S1	129.9 (3)	C10—C11—S2	111.7 (2)
C2—C1—S1	109.2 (2)	C12—C11—S2	120.3 (2)
N1—C2—C3	125.9 (3)	N2—C12—C11	124.4 (3)
N1—C2—C1	115.2 (3)	N2—C12—S3	116.0 (2)
C3—C2—C1	118.9 (3)	C11—C12—S3	119.5 (2)
C4—C3—C2	119.3 (3)	C18—C13—C14	121.4 (3)
C4—C3—H3	120.4	C18—C13—S3	129.3 (3)
C2—C3—H3	120.4	C14—C13—S3	109.2 (2)
C3—C4—C5	121.5 (3)	C15—C14—N2	124.7 (3)
C3—C4—H4	119.3	C15—C14—C13	119.4 (3)
C5—C4—H4	119.3	N2—C14—C13	115.9 (3)
C6—C5—C4	120.8 (3)	C16—C15—C14	118.3 (3)
C6—C5—H5	119.6	C16—C15—H15	120.9
C4—C5—H5	119.6	C14—C15—H15	120.9
C5—C6—C1	118.6 (3)	C15—C16—C17	122.2 (3)
C5—C6—H6	120.7	C15—C16—H16	118.9
C1—C6—H6	120.7	C17—C16—H16	118.9
N1—C7—C8	124.3 (3)	C18—C17—C16	120.3 (3)
N1—C7—S1	115.5 (2)	C18—C17—H17	119.8
C8—C7—S1	120.2 (2)	C16—C17—H17	119.8
C9—C8—C7	129.4 (3)	C17—C18—C13	118.3 (3)
C9—C8—S2	111.5 (2)	C17—C18—H18	120.8
C7—C8—S2	119.1 (2)	C13—C18—H18	120.8
C8—C9—C10	113.0 (3)
C7—S1—C1—C6	−178.8 (3)	C9—C10—C11—C12	−179.3 (2)
C7—S1—C1—C2	0.3 (2)	C9—C10—C11—S2	−0.9 (3)
C7—N1—C2—C3	−179.5 (3)	C8—S2—C11—C10	0.7 (2)
C7—N1—C2—C1	0.5 (3)	C8—S2—C11—C12	179.2 (2)
C6—C1—C2—N1	178.7 (2)	C14—N2—C12—C11	179.5 (2)
S1—C1—C2—N1	−0.5 (3)	C14—N2—C12—S3	−0.6 (3)
C6—C1—C2—C3	−1.3 (4)	C10—C11—C12—N2	−176.7 (3)
S1—C1—C2—C3	179.5 (2)	S2—C11—C12—N2	5.1 (4)
N1—C2—C3—C4	−179.5 (3)	C10—C11—C12—S3	3.4 (4)
C1—C2—C3—C4	0.5 (4)	S2—C11—C12—S3	−174.81 (13)
C2—C3—C4—C5	0.3 (5)	C13—S3—C12—N2	0.6 (2)
C3—C4—C5—C6	−0.3 (5)	C13—S3—C12—C11	−179.5 (2)
C4—C5—C6—C1	−0.6 (5)	C12—S3—C13—C18	−179.6 (3)
C2—C1—C6—C5	1.4 (4)	C12—S3—C13—C14	−0.4 (2)
S1—C1—C6—C5	−179.6 (2)	C12—N2—C14—C15	−178.8 (3)
C2—N1—C7—C8	−180.0 (2)	C12—N2—C14—C13	0.2 (3)
C2—N1—C7—S1	−0.3 (3)	C18—C13—C14—C15	−1.5 (4)
C1—S1—C7—N1	0.0 (2)	S3—C13—C14—C15	179.3 (2)
C1—S1—C7—C8	179.7 (2)	C18—C13—C14—N2	179.4 (2)
N1—C7—C8—C9	−174.9 (3)	S3—C13—C14—N2	0.2 (3)
S1—C7—C8—C9	5.4 (4)	N2—C14—C15—C16	179.2 (2)
N1—C7—C8—S2	5.6 (4)	C13—C14—C15—C16	0.3 (4)
S1—C7—C8—S2	−174.02 (14)	C14—C15—C16—C17	1.2 (4)
C11—S2—C8—C9	−0.3 (2)	C15—C16—C17—C18	−1.4 (5)
C11—S2—C8—C7	179.2 (2)	C16—C17—C18—C13	0.1 (4)
C7—C8—C9—C10	−179.6 (2)	C14—C13—C18—C17	1.3 (4)
S2—C8—C9—C10	−0.1 (3)	S3—C13—C18—C17	−179.7 (2)
C8—C9—C10—C11	0.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···N1i	0.95	2.63	3.444 (4)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯N1i	0.95	2.63	3.444 (4)	144

Symmetry code: (i) .