4,4'-Diphenyl-2,2'-bi-1,3-thia-zole.

In the centrosymmetric title compound, C(18)H(12)N(2)S(24), the five- (r.m.s. deviation = 0.002 Å) and six-membered (r.m.s. deviation = 0.002 Å) rings are essentially coplanar [dihedral angle between rings = 1.9 (1)°].

Related literature

For the crystal structures of other 4,4′-disubstituted compounds, see: Bolognesi et al. (1987 ▶); Craig et al. (1988 ▶); Curtis et al. (2004 ▶).

Experimental

Crystal data

C18H12N2S2

M = 320.42

Monoclinic,

a = 5.7769 (4) Å

b = 7.6573 (5) Å

c = 17.1960 (12) Å

β = 99.614 (1)°

V = 749.99 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.35 mm−1

T = 100 K

0.30 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.902, T max = 0.966

6993 measured reflections

1730 independent reflections

1575 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.079

S = 1.04

1730 reflections

100 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.24 e Å−3

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: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810027261/nk2046sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810027261/nk2046Isup2.hkl

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

C18H12N2S2	F(000) = 332
Mr = 320.42	Dx = 1.419 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4091 reflections
a = 5.7769 (4) Å	θ = 2.4–28.3°
b = 7.6573 (5) Å	µ = 0.35 mm−1
c = 17.1960 (12) Å	T = 100 K
β = 99.614 (1)°	Prism, colorless
V = 749.99 (9) Å3	0.30 × 0.10 × 0.10 mm
Z = 2

Bruker SMART APEX diffractometer	1730 independent reflections
Radiation source: fine-focus sealed tube	1575 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω scans	θmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.902, Tmax = 0.966	k = −9→9
6993 measured reflections	l = −21→22

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0421P)2 + 0.350P] where P = (Fo2 + 2Fc2)/3
1730 reflections	(Δ/σ)max = 0.001
100 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

	x	y	z	Uiso*/Ueq
S1	0.76174 (5)	0.35670 (4)	0.446214 (17)	0.01797 (12)
N1	0.35546 (18)	0.49301 (13)	0.39798 (6)	0.0151 (2)
C1	0.2750 (2)	0.43006 (15)	0.25545 (7)	0.0139 (2)
C2	0.0586 (2)	0.51551 (16)	0.24862 (7)	0.0156 (2)
H2	0.0132	0.5690	0.2936	0.019*
C3	−0.0906 (2)	0.52260 (16)	0.17611 (7)	0.0179 (3)
H3	−0.2377	0.5804	0.1719	0.022*
C4	−0.0255 (2)	0.44574 (17)	0.10999 (7)	0.0198 (3)
H4	−0.1278	0.4505	0.0607	0.024*
C5	0.1903 (2)	0.36157 (16)	0.11614 (7)	0.0193 (3)
H5	0.2355	0.3094	0.0708	0.023*
C6	0.3399 (2)	0.35345 (15)	0.18827 (7)	0.0165 (3)
H6	0.4868	0.2957	0.1921	0.020*
C7	0.4293 (2)	0.41960 (15)	0.33292 (7)	0.0140 (2)
C8	0.6444 (2)	0.34026 (16)	0.34867 (7)	0.0167 (3)
H8	0.7186	0.2835	0.3103	0.020*
C9	0.5133 (2)	0.46895 (15)	0.46100 (7)	0.0150 (2)

	U11	U22	U33	U12	U13	U23
S1	0.01731 (17)	0.02092 (18)	0.01515 (17)	0.00472 (11)	0.00112 (12)	−0.00100 (11)
N1	0.0165 (5)	0.0146 (5)	0.0145 (5)	−0.0003 (4)	0.0035 (4)	0.0003 (4)
C1	0.0159 (6)	0.0113 (5)	0.0149 (6)	−0.0023 (4)	0.0038 (4)	0.0007 (4)
C2	0.0166 (6)	0.0142 (6)	0.0167 (6)	−0.0010 (4)	0.0046 (5)	−0.0004 (4)
C3	0.0156 (6)	0.0155 (6)	0.0221 (6)	−0.0006 (4)	0.0014 (5)	0.0004 (5)
C4	0.0229 (7)	0.0179 (6)	0.0167 (6)	−0.0023 (5)	−0.0020 (5)	−0.0003 (5)
C5	0.0256 (7)	0.0179 (6)	0.0147 (6)	−0.0011 (5)	0.0044 (5)	−0.0030 (4)
C6	0.0180 (6)	0.0149 (6)	0.0172 (6)	0.0006 (4)	0.0040 (5)	−0.0007 (4)
C7	0.0168 (6)	0.0115 (5)	0.0145 (5)	−0.0017 (4)	0.0043 (4)	−0.0004 (4)
C8	0.0187 (6)	0.0176 (6)	0.0141 (5)	0.0006 (4)	0.0034 (4)	−0.0013 (4)
C9	0.0164 (6)	0.0134 (5)	0.0157 (6)	0.0001 (4)	0.0041 (4)	0.0001 (4)

S1—C8	1.7056 (12)	C3—H3	0.9500
S1—C9	1.7278 (12)	C4—C5	1.3914 (18)
N1—C9	1.3076 (15)	C4—H4	0.9500
N1—C7	1.3817 (15)	C5—C6	1.3897 (17)
C1—C2	1.3981 (16)	C5—H5	0.9500
C1—C6	1.4013 (16)	C6—H6	0.9500
C1—C7	1.4762 (16)	C7—C8	1.3690 (17)
C2—C3	1.3934 (17)	C8—H8	0.9500
C2—H2	0.9500	C9—C9i	1.455 (2)
C3—C4	1.3870 (18)
C8—S1—C9	88.74 (6)	C6—C5—H5	119.9
C9—N1—C7	110.30 (10)	C4—C5—H5	119.9
C2—C1—C6	119.02 (11)	C5—C6—C1	120.33 (11)
C2—C1—C7	119.86 (11)	C5—C6—H6	119.8
C6—C1—C7	121.11 (11)	C1—C6—H6	119.8
C3—C2—C1	120.28 (11)	C8—C7—N1	114.40 (11)
C3—C2—H2	119.9	C8—C7—C1	126.45 (11)
C1—C2—H2	119.9	N1—C7—C1	119.14 (10)
C4—C3—C2	120.33 (11)	C7—C8—S1	111.12 (9)
C4—C3—H3	119.8	C7—C8—H8	124.4
C2—C3—H3	119.8	S1—C8—H8	124.4
C3—C4—C5	119.76 (11)	N1—C9—C9i	123.47 (14)
C3—C4—H4	120.1	N1—C9—S1	115.44 (9)
C5—C4—H4	120.1	C9i—C9—S1	121.09 (12)
C6—C5—C4	120.27 (11)
C6—C1—C2—C3	0.60 (17)	C6—C1—C7—C8	0.67 (18)
C7—C1—C2—C3	−178.53 (11)	C2—C1—C7—N1	0.83 (16)
C1—C2—C3—C4	−0.32 (18)	C6—C1—C7—N1	−178.29 (11)
C2—C3—C4—C5	−0.17 (18)	N1—C7—C8—S1	−0.35 (13)
C3—C4—C5—C6	0.36 (19)	C1—C7—C8—S1	−179.35 (9)
C4—C5—C6—C1	−0.06 (18)	C9—S1—C8—C7	0.34 (10)
C2—C1—C6—C5	−0.41 (17)	C7—N1—C9—C9i	−179.94 (14)
C7—C1—C6—C5	178.71 (11)	C7—N1—C9—S1	0.14 (13)
C9—N1—C7—C8	0.13 (15)	C8—S1—C9—N1	−0.28 (10)
C9—N1—C7—C1	179.22 (10)	C8—S1—C9—C9i	179.80 (14)
C2—C1—C7—C8	179.79 (12)