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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): o2030.
Published online 2010 July 17. doi:  10.1107/S1600536810027261
PMCID: PMC3007272

4,4′-Diphenyl-2,2′-bi-1,3-thia­zole

Abstract

In the centrosymmetric title compound, C18H12N2S24, 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 [triangle]); Craig et al. (1988 [triangle]); Curtis et al. (2004 [triangle]).

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Object name is e-66-o2030-scheme1.jpg

Experimental

Crystal data

  • C18H12N2S2
  • M r = 320.42
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2030-efi1.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Supplementary Material

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

Acknowledgments

I thank the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

2,2'-Bithiazole and other 4,4'-disubstituted derivatives possess a pair of nitrogen-donor sites that renders such molecules capable of chelating metal atoms. The crystal structure of the parent compound as well as those of the methyl and ethyl substituted derivatives have been reported (Bolognesi et al., 1987; Craig et al., 1988, Curtis et al., 2004). These molecules are centrosymmetric compounds having an inversion center midway along the Cazolyl–Cazolyl bond. In the parent compound, this bond is 1.468 (6) Å (Bolognesi et al., 1987). The bond is somewhat shortened to 1.455 (2) Å in the phenyl analog (Scheme I, Fig. 1).

Experimental

The organic compound was returned unchanged in an attempted reaction of lead(II) nitrate (0.13 mmol, 0.04 g) with 4,4'-diphenyl-2,2'-bithiazole (0.25 mmol, 0.08 g) in the presence of potassium thiocyanate (0.25 mmol, 0.03 g) in a methanol/THF mixture. Crystals were obtained after one week of setting the mixture aside.

Refinement

Hydrogen atoms were placed in calculated positions (C–H 0.95 Å) and included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C).

Figures

Fig. 1.
Displacement ellipsoid plot (Barbour, 2001) of C18H12N2S2 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. The molecule lies on an inversion center.

Crystal data

C18H12N2S2F(000) = 332
Mr = 320.42Dx = 1.419 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4091 reflections
a = 5.7769 (4) Åθ = 2.4–28.3°
b = 7.6573 (5) ŵ = 0.35 mm1
c = 17.1960 (12) ÅT = 100 K
β = 99.614 (1)°Prism, colorless
V = 749.99 (9) Å30.30 × 0.10 × 0.10 mm
Z = 2

Data collection

Bruker SMART APEX diffractometer1730 independent reflections
Radiation source: fine-focus sealed tube1575 reflections with I > 2σ(I)
graphiteRint = 0.026
ω scansθmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −7→7
Tmin = 0.902, Tmax = 0.966k = −9→9
6993 measured reflectionsl = −21→22

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0421P)2 + 0.350P] where P = (Fo2 + 2Fc2)/3
1730 reflections(Δ/σ)max = 0.001
100 parametersΔρmax = 0.42 e Å3
0 restraintsΔρmin = −0.24 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
S10.76174 (5)0.35670 (4)0.446214 (17)0.01797 (12)
N10.35546 (18)0.49301 (13)0.39798 (6)0.0151 (2)
C10.2750 (2)0.43006 (15)0.25545 (7)0.0139 (2)
C20.0586 (2)0.51551 (16)0.24862 (7)0.0156 (2)
H20.01320.56900.29360.019*
C3−0.0906 (2)0.52260 (16)0.17611 (7)0.0179 (3)
H3−0.23770.58040.17190.022*
C4−0.0255 (2)0.44574 (17)0.10999 (7)0.0198 (3)
H4−0.12780.45050.06070.024*
C50.1903 (2)0.36157 (16)0.11614 (7)0.0193 (3)
H50.23550.30940.07080.023*
C60.3399 (2)0.35345 (15)0.18827 (7)0.0165 (3)
H60.48680.29570.19210.020*
C70.4293 (2)0.41960 (15)0.33292 (7)0.0140 (2)
C80.6444 (2)0.34026 (16)0.34867 (7)0.0167 (3)
H80.71860.28350.31030.020*
C90.5133 (2)0.46895 (15)0.46100 (7)0.0150 (2)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.01731 (17)0.02092 (18)0.01515 (17)0.00472 (11)0.00112 (12)−0.00100 (11)
N10.0165 (5)0.0146 (5)0.0145 (5)−0.0003 (4)0.0035 (4)0.0003 (4)
C10.0159 (6)0.0113 (5)0.0149 (6)−0.0023 (4)0.0038 (4)0.0007 (4)
C20.0166 (6)0.0142 (6)0.0167 (6)−0.0010 (4)0.0046 (5)−0.0004 (4)
C30.0156 (6)0.0155 (6)0.0221 (6)−0.0006 (4)0.0014 (5)0.0004 (5)
C40.0229 (7)0.0179 (6)0.0167 (6)−0.0023 (5)−0.0020 (5)−0.0003 (5)
C50.0256 (7)0.0179 (6)0.0147 (6)−0.0011 (5)0.0044 (5)−0.0030 (4)
C60.0180 (6)0.0149 (6)0.0172 (6)0.0006 (4)0.0040 (5)−0.0007 (4)
C70.0168 (6)0.0115 (5)0.0145 (5)−0.0017 (4)0.0043 (4)−0.0004 (4)
C80.0187 (6)0.0176 (6)0.0141 (5)0.0006 (4)0.0034 (4)−0.0013 (4)
C90.0164 (6)0.0134 (5)0.0157 (6)0.0001 (4)0.0041 (4)0.0001 (4)

Geometric parameters (Å, °)

S1—C81.7056 (12)C3—H30.9500
S1—C91.7278 (12)C4—C51.3914 (18)
N1—C91.3076 (15)C4—H40.9500
N1—C71.3817 (15)C5—C61.3897 (17)
C1—C21.3981 (16)C5—H50.9500
C1—C61.4013 (16)C6—H60.9500
C1—C71.4762 (16)C7—C81.3690 (17)
C2—C31.3934 (17)C8—H80.9500
C2—H20.9500C9—C9i1.455 (2)
C3—C41.3870 (18)
C8—S1—C988.74 (6)C6—C5—H5119.9
C9—N1—C7110.30 (10)C4—C5—H5119.9
C2—C1—C6119.02 (11)C5—C6—C1120.33 (11)
C2—C1—C7119.86 (11)C5—C6—H6119.8
C6—C1—C7121.11 (11)C1—C6—H6119.8
C3—C2—C1120.28 (11)C8—C7—N1114.40 (11)
C3—C2—H2119.9C8—C7—C1126.45 (11)
C1—C2—H2119.9N1—C7—C1119.14 (10)
C4—C3—C2120.33 (11)C7—C8—S1111.12 (9)
C4—C3—H3119.8C7—C8—H8124.4
C2—C3—H3119.8S1—C8—H8124.4
C3—C4—C5119.76 (11)N1—C9—C9i123.47 (14)
C3—C4—H4120.1N1—C9—S1115.44 (9)
C5—C4—H4120.1C9i—C9—S1121.09 (12)
C6—C5—C4120.27 (11)
C6—C1—C2—C30.60 (17)C6—C1—C7—C80.67 (18)
C7—C1—C2—C3−178.53 (11)C2—C1—C7—N10.83 (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—C60.36 (19)C1—C7—C8—S1−179.35 (9)
C4—C5—C6—C1−0.06 (18)C9—S1—C8—C70.34 (10)
C2—C1—C6—C5−0.41 (17)C7—N1—C9—C9i−179.94 (14)
C7—C1—C6—C5178.71 (11)C7—N1—C9—S10.14 (13)
C9—N1—C7—C80.13 (15)C8—S1—C9—N1−0.28 (10)
C9—N1—C7—C1179.22 (10)C8—S1—C9—C9i179.80 (14)
C2—C1—C7—C8179.79 (12)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NK2046).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bolognesi, A., Catellani, M., Destri, S. & Porzio, W. (1987). Acta Cryst. C43, 1171–1173.
  • Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Craig, D. C., Goodwin, H. A., Onggo, D. & Rae, A. D. (1988). Aust. J. Chem.41, 1625–1644.
  • Curtis, D., Cao, J. & Kampf, J. F. (2004). J. Am. Chem. Soc.126, 4318–4328. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography