Bis[(5-phenyl-1,3,4-thia-diazol-2-yl)sulfan-yl]methane.

The asymmetric unit of the title compound, C(17)H(12)N(4)S(4), contains one half-mol-ecule situated on a twofold rotational axis. In the mol-ecule, the thia-diazole and attached phenyl rings are twisted by 5.8 (3)°.

Related literature

For biological activity of 1,3,4-thia­diazole derivatives, see: Nakagawa et al. (1996 ▶); Wang et al. (1999 ▶); Carvalho et al. (2004 ▶); Riente et al. (2009 ▶); Poorrajab et al. (2009 ▶).

Experimental

Crystal data

C17H12N4S4

M = 400.55

Orthorhombic,

a = 10.805 (2) Å

b = 19.287 (4) Å

c = 4.0738 (8) Å

V = 848.9 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.57 mm−1

T = 113 K

0.20 × 0.18 × 0.10 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.895, T max = 0.945

6754 measured reflections

1477 independent reflections

1421 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.124

S = 1.03

1477 reflections

115 parameters

H-atom parameters constrained

Δρmax = 0.54 e Å−3

Δρmin = −0.55 e Å−3

Absolute structure: Flack (1983 ▶), 554 Friedel pairs

Flack parameter: 0.16 (14)

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810044442/cv2783sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810044442/cv2783Isup2.hkl

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

C17H12N4S4	F(000) = 412
Mr = 400.55	Dx = 1.567 Mg m−3
Orthorhombic, P21212	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2ab	Cell parameters from 2856 reflections
a = 10.805 (2) Å	θ = 2.1–27.9°
b = 19.287 (4) Å	µ = 0.57 mm−1
c = 4.0738 (8) Å	T = 113 K
V = 848.9 (3) Å3	Prism, colourless
Z = 2	0.20 × 0.18 × 0.10 mm

Rigaku Saturn CCD area-detector diffractometer	1477 independent reflections
Radiation source: rotating anode	1421 reflections with I > 2σ(I)
confocal	Rint = 0.028
Detector resolution: 7.31 pixels mm-1	θmax = 25.0°, θmin = 2.1°
φ and ω scans	h = −12→12
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −22→22
Tmin = 0.895, Tmax = 0.945	l = −4→4
6754 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.029	w = 1/[σ2(Fo2) + (0.110P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.124	(Δ/σ)max = 0.001
S = 1.02	Δρmax = 0.54 e Å−3
1477 reflections	Δρmin = −0.55 e Å−3
115 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.049 (10)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 554 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.16 (14)

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	Occ. (<1)
S1	0.19317 (6)	0.33910 (3)	0.3294 (2)	0.0215 (3)
S2	0.13644 (6)	0.47579 (4)	0.6577 (2)	0.0216 (3)
N1	−0.0251 (2)	0.29797 (13)	0.4770 (7)	0.0223 (6)
N2	−0.0161 (2)	0.36481 (13)	0.6002 (7)	0.0231 (6)
C1	−0.0141 (3)	0.16581 (16)	0.1495 (9)	0.0260 (7)
H1	−0.0904	0.1795	0.2453	0.031*
C2	−0.0048 (3)	0.10272 (16)	−0.0079 (9)	0.0289 (8)
H2	−0.0748	0.0731	−0.0206	0.035*
C3	0.1073 (3)	0.08236 (15)	−0.1485 (9)	0.0279 (7)
H3	0.1136	0.0389	−0.2568	0.033*
C4	0.2085 (3)	0.12546 (15)	−0.1299 (9)	0.0262 (7)
H4	0.2847	0.1117	−0.2264	0.031*
C5	0.1999 (3)	0.18852 (16)	0.0284 (8)	0.0234 (7)
H5	0.2704	0.2178	0.0420	0.028*
C6	0.0885 (3)	0.20960 (14)	0.1682 (8)	0.0196 (6)
C7	0.0747 (2)	0.27771 (15)	0.3277 (7)	0.0181 (6)
C8	0.0919 (3)	0.39217 (14)	0.5395 (8)	0.0192 (7)
C9	0.0000	0.5000	0.8888 (11)	0.0229 (10)
H9A	0.0223	0.5394	1.0330	0.027*	0.50
H9B	−0.0223	0.4606	1.0330	0.027*	0.50

	U11	U22	U33	U12	U13	U23
S1	0.0163 (4)	0.0229 (4)	0.0252 (5)	−0.0010 (3)	0.0012 (4)	−0.0011 (3)
S2	0.0221 (4)	0.0204 (4)	0.0223 (5)	−0.0011 (3)	−0.0018 (4)	0.0005 (3)
N1	0.0199 (12)	0.0197 (12)	0.0273 (14)	0.0005 (9)	−0.0006 (12)	0.0018 (12)
N2	0.0229 (12)	0.0200 (12)	0.0263 (15)	0.0006 (10)	0.0035 (11)	−0.0007 (12)
C1	0.0198 (14)	0.0279 (15)	0.0303 (18)	0.0002 (11)	0.0039 (16)	0.0029 (17)
C2	0.0258 (14)	0.0254 (15)	0.036 (2)	−0.0019 (12)	−0.0060 (17)	−0.0012 (16)
C3	0.0374 (17)	0.0206 (13)	0.0257 (17)	0.0052 (13)	0.0029 (17)	−0.0019 (15)
C4	0.0244 (14)	0.0254 (14)	0.0289 (18)	0.0079 (12)	0.0013 (15)	0.0031 (16)
C5	0.0208 (14)	0.0232 (14)	0.0260 (17)	0.0012 (12)	−0.0002 (15)	0.0041 (14)
C6	0.0189 (14)	0.0209 (14)	0.0191 (15)	0.0028 (11)	−0.0046 (13)	0.0043 (14)
C7	0.0162 (13)	0.0216 (13)	0.0166 (14)	0.0000 (11)	−0.0015 (13)	0.0033 (13)
C8	0.0206 (14)	0.0198 (12)	0.0170 (15)	0.0038 (11)	−0.0010 (13)	−0.0001 (12)
C9	0.029 (2)	0.0235 (19)	0.016 (2)	−0.0003 (17)	0.000	0.000

S1—C8	1.726 (3)	C2—H2	0.9500
S1—C7	1.744 (3)	C3—C4	1.376 (5)
S2—C8	1.751 (3)	C3—H3	0.9500
S2—C9	1.810 (2)	C4—C5	1.380 (5)
N1—C7	1.298 (4)	C4—H4	0.9500
N1—N2	1.387 (4)	C5—C6	1.391 (4)
N2—C8	1.304 (4)	C5—H5	0.9500
C1—C2	1.379 (5)	C6—C7	1.473 (4)
C1—C6	1.396 (4)	C9—S2i	1.810 (2)
C1—H1	0.9500	C9—H9A	0.9900
C2—C3	1.396 (4)	C9—H9B	0.9900
C8—S1—C7	86.51 (14)	C4—C5—H5	119.8
C8—S2—C9	99.02 (10)	C6—C5—H5	119.8
C7—N1—N2	113.0 (2)	C5—C6—C1	119.2 (3)
C8—N2—N1	111.8 (2)	C5—C6—C7	121.9 (3)
C2—C1—C6	120.1 (3)	C1—C6—C7	118.9 (3)
C2—C1—H1	119.9	N1—C7—C6	124.0 (3)
C6—C1—H1	119.9	N1—C7—S1	113.8 (2)
C1—C2—C3	120.1 (3)	C6—C7—S1	122.2 (2)
C1—C2—H2	119.9	N2—C8—S1	114.9 (2)
C3—C2—H2	119.9	N2—C8—S2	124.5 (2)
C4—C3—C2	119.8 (3)	S1—C8—S2	120.57 (17)
C4—C3—H3	120.1	S2—C9—S2i	117.3 (2)
C2—C3—H3	120.1	S2—C9—H9A	108.0
C3—C4—C5	120.3 (3)	S2i—C9—H9A	108.0
C3—C4—H4	119.9	S2—C9—H9B	108.0
C5—C4—H4	119.9	S2i—C9—H9B	108.0
C4—C5—C6	120.5 (3)	H9A—C9—H9B	107.2
C7—N1—N2—C8	−0.5 (4)	C1—C6—C7—N1	5.7 (5)
C6—C1—C2—C3	0.1 (5)	C5—C6—C7—S1	4.3 (4)
C1—C2—C3—C4	0.0 (5)	C1—C6—C7—S1	−173.9 (3)
C2—C3—C4—C5	0.3 (6)	C8—S1—C7—N1	−1.1 (2)
C3—C4—C5—C6	−0.6 (5)	C8—S1—C7—C6	178.6 (3)
C4—C5—C6—C1	0.7 (5)	N1—N2—C8—S1	−0.4 (3)
C4—C5—C6—C7	−177.6 (3)	N1—N2—C8—S2	179.9 (2)
C2—C1—C6—C5	−0.4 (5)	C7—S1—C8—N2	0.8 (3)
C2—C1—C6—C7	177.9 (3)	C7—S1—C8—S2	−179.5 (2)
N2—N1—C7—C6	−178.6 (2)	C9—S2—C8—N2	4.3 (3)
N2—N1—C7—S1	1.1 (3)	C9—S2—C8—S1	−175.34 (19)
C5—C6—C7—N1	−176.0 (3)	C8—S2—C9—S2i	−76.74 (11)