4,4′-Diphenyl-2,2′-bi-1,3-thia­zole

Ng, S.W.

doi:10.1107/S1600536810027261

organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page o2030

https://doi.org/10.1107/S1600536810027261

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4,4′-Diphenyl-2,2′-bi-1,3-thiazole

Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 8 July 2010; accepted 9 July 2010; online 17 July 2010)

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 ); Craig et al. (1988 ); Curtis et al. (2004 ).

Experimental

Crystal data

C₁₈H₁₂N₂S₂
M_r = 320.42
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.028
wR(F²) = 0.079
S = 1.04
1730 reflections
100 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −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 ).

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810027261/nk2046Isup2.hkl

checkCIF report

Comment top

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 C_azolyl–C_azolyl 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).

Related literature top

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

Experimental top

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.

Structure description top

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

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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).

Figures top

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.

4,4'-Diphenyl-2,2'-bi-1,3-thiazole top

Crystal data top

C₁₈H₁₂N₂S₂	F(000) = 332
M_r = 320.42	D_x = 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

Data collection top

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

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.079	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0421P)² + 0.350P] where P = (F_o² + 2F_c²)/3
1730 reflections	(Δ/σ)_max = 0.001
100 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₈H₁₂N₂S₂	V = 749.99 (9) Å³
M_r = 320.42	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.7769 (4) Å	µ = 0.35 mm⁻¹
b = 7.6573 (5) Å	T = 100 K
c = 17.1960 (12) Å	0.30 × 0.10 × 0.10 mm
β = 99.614 (1)°

Data collection top

Bruker SMART APEX diffractometer	1730 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1575 reflections with I > 2σ(I)
T_min = 0.902, T_max = 0.966	R_int = 0.026
6993 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.079	H-atom parameters constrained
S = 1.04	Δρ_max = 0.42 e Å⁻³
1730 reflections	Δρ_min = −0.24 e Å⁻³
100 parameters

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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₂N₂S₂
M_r	320.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	5.7769 (4), 7.6573 (5), 17.1960 (12)
β (°)	99.614 (1)
V (Å³)	749.99 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.30 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.902, 0.966
No. of measured, independent and observed [I > 2σ(I)] reflections	6993, 1730, 1575
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.079, 1.04
No. of reflections	1730
No. of parameters	100
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.24

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Acknowledgements

I thank the University of Malaya for supporting this study.

References

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