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

The asymmetric unit of the title compound, C(20)H(18)N(4)S(4), contains one half-mol-ecule situated on a twofold rotation axis, in which the thia-diazole and phenyl rings are twisted by 7.2 (3)°. In the crystal, weak inter-molecular C-H⋯π inter-actions link the mol-ecules into layers parallel to (103).

Related literature

For the biological activity of 1,3,4-triazole derivatives, see: Nakagawa et al. (1996 ▶); Wang et al. (1999 ▶). For the crystal structure of bis­(5-phenyl-1,3,4-thia­diazol-2-ylsulfan­yl)meth­ane, see: Wang et al. (2010 ▶).

Experimental

Crystal data

C20H18N4S4

M = 442.62

Monoclinic,

a = 5.7976 (7) Å

b = 13.4393 (14) Å

c = 12.9784 (12) Å

β = 99.120 (7)°

V = 998.44 (18) Å3

Z = 2

Mo Kα radiation

μ = 0.49 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 = 0.908, T max = 0.953

9992 measured reflections

2384 independent reflections

1870 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.088

S = 1.06

2384 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.22 e Å−3

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/S1600536811006064/cv5053sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811006064/cv5053Isup2.hkl

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

C20H18N4S4	F(000) = 460
Mr = 442.62	Dx = 1.472 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3630 reflections
a = 5.7976 (7) Å	θ = 1.5–27.9°
b = 13.4393 (14) Å	µ = 0.49 mm−1
c = 12.9784 (12) Å	T = 113 K
β = 99.120 (7)°	Prism, colorless
V = 998.44 (18) Å3	0.20 × 0.18 × 0.10 mm
Z = 2

Rigaku Saturn CCD area-detector diffractometer	2384 independent reflections
Radiation source: rotating anode	1870 reflections with I > 2σ(I)
multilayer	Rint = 0.038
Detector resolution: 14.63 pixels mm-1	θmax = 27.9°, θmin = 2.2°
φ and ω scans	h = −7→7
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −17→17
Tmin = 0.908, Tmax = 0.953	l = −15→16
9992 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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0495P)2] where P = (Fo2 + 2Fc2)/3
2384 reflections	(Δ/σ)max = 0.001
127 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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
S1	1.18924 (6)	0.48167 (3)	0.35236 (3)	0.01929 (12)
S2	0.94277 (7)	0.60479 (3)	0.17655 (3)	0.02206 (13)
N1	0.8027 (2)	0.39565 (9)	0.36814 (10)	0.0221 (3)
N2	0.7508 (2)	0.46308 (10)	0.28684 (10)	0.0206 (3)
C1	1.3577 (3)	0.34573 (11)	0.54385 (12)	0.0210 (3)
H1	1.4506	0.3955	0.5185	0.025*
C2	1.4532 (3)	0.28628 (12)	0.62747 (12)	0.0213 (3)
H2	1.6099	0.2969	0.6601	0.026*
C3	1.3224 (3)	0.21206 (12)	0.66341 (12)	0.0237 (4)
H3	1.3889	0.1710	0.7199	0.028*
C4	1.0921 (3)	0.19787 (12)	0.61620 (13)	0.0259 (4)
H4	1.0013	0.1469	0.6409	0.031*
C5	0.9936 (3)	0.25738 (12)	0.53341 (12)	0.0216 (3)
H5	0.8363	0.2469	0.5015	0.026*
C6	1.1262 (3)	0.33270 (11)	0.49711 (11)	0.0173 (3)
C7	1.0225 (3)	0.39663 (11)	0.40992 (12)	0.0171 (3)
C8	0.9342 (3)	0.51325 (11)	0.27088 (12)	0.0175 (3)
C9	0.6507 (3)	0.59299 (11)	0.10328 (12)	0.0211 (3)
H9A	0.5373	0.5895	0.1527	0.025*
H9B	0.6143	0.6531	0.0597	0.025*
C10	0.6215 (2)	0.50122 (11)	0.03322 (12)	0.0205 (3)
H10A	0.6445	0.4405	0.0769	0.025*
H10B	0.7419	0.5018	−0.0130	0.025*

	U11	U22	U33	U12	U13	U23
S1	0.01581 (19)	0.0215 (2)	0.0199 (2)	−0.00349 (15)	0.00081 (16)	0.00081 (15)
S2	0.0213 (2)	0.0229 (2)	0.0209 (2)	−0.00350 (16)	−0.00005 (17)	0.00217 (16)
N1	0.0185 (7)	0.0276 (7)	0.0199 (7)	−0.0024 (6)	0.0025 (6)	0.0024 (6)
N2	0.0171 (6)	0.0260 (7)	0.0185 (7)	−0.0008 (6)	0.0021 (5)	0.0017 (5)
C1	0.0198 (8)	0.0196 (8)	0.0232 (9)	−0.0048 (6)	0.0025 (7)	−0.0012 (6)
C2	0.0160 (7)	0.0247 (8)	0.0224 (9)	−0.0007 (6)	−0.0003 (6)	−0.0022 (7)
C3	0.0249 (8)	0.0251 (9)	0.0208 (8)	0.0021 (7)	0.0027 (7)	0.0039 (7)
C4	0.0235 (8)	0.0267 (9)	0.0286 (9)	−0.0040 (7)	0.0072 (7)	0.0057 (7)
C5	0.0155 (7)	0.0267 (8)	0.0223 (9)	−0.0040 (6)	0.0025 (6)	−0.0008 (7)
C6	0.0189 (7)	0.0175 (7)	0.0159 (8)	−0.0003 (6)	0.0041 (6)	−0.0036 (6)
C7	0.0168 (7)	0.0184 (7)	0.0169 (8)	−0.0024 (6)	0.0052 (6)	−0.0038 (6)
C8	0.0172 (7)	0.0208 (8)	0.0140 (8)	0.0004 (6)	0.0010 (6)	−0.0040 (6)
C9	0.0194 (8)	0.0221 (8)	0.0207 (9)	0.0017 (6)	−0.0008 (7)	0.0015 (6)
C10	0.0184 (8)	0.0224 (8)	0.0194 (8)	0.0023 (6)	−0.0007 (6)	0.0003 (6)

S1—C8	1.7289 (15)	C3—H3	0.9500
S1—C7	1.7400 (15)	C4—C5	1.388 (2)
S2—C8	1.7417 (16)	C4—H4	0.9500
S2—C9	1.8126 (15)	C5—C6	1.397 (2)
N1—C7	1.303 (2)	C5—H5	0.9500
N1—N2	1.3872 (17)	C6—C7	1.471 (2)
N2—C8	1.303 (2)	C9—C10	1.526 (2)
C1—C2	1.390 (2)	C9—H9A	0.9900
C1—C6	1.393 (2)	C9—H9B	0.9900
C1—H1	0.9500	C10—C10i	1.531 (3)
C2—C3	1.379 (2)	C10—H10A	0.9900
C2—H2	0.9500	C10—H10B	0.9900
C3—C4	1.391 (2)
C8—S1—C7	86.82 (7)	C1—C6—C7	120.63 (14)
C8—S2—C9	100.29 (7)	C5—C6—C7	120.18 (13)
C7—N1—N2	112.95 (13)	N1—C7—C6	124.58 (14)
C8—N2—N1	112.01 (12)	N1—C7—S1	113.64 (12)
C2—C1—C6	120.32 (15)	C6—C7—S1	121.78 (11)
C2—C1—H1	119.8	N2—C8—S1	114.58 (12)
C6—C1—H1	119.8	N2—C8—S2	126.30 (12)
C3—C2—C1	120.49 (14)	S1—C8—S2	119.11 (9)
C3—C2—H2	119.8	C10—C9—S2	112.94 (11)
C1—C2—H2	119.8	C10—C9—H9A	109.0
C2—C3—C4	119.44 (15)	S2—C9—H9A	109.0
C2—C3—H3	120.3	C10—C9—H9B	109.0
C4—C3—H3	120.3	S2—C9—H9B	109.0
C5—C4—C3	120.70 (15)	H9A—C9—H9B	107.8
C5—C4—H4	119.6	C9—C10—C10i	111.00 (16)
C3—C4—H4	119.6	C9—C10—H10A	109.4
C4—C5—C6	119.84 (15)	C10i—C10—H10A	109.4
C4—C5—H5	120.1	C9—C10—H10B	109.4
C6—C5—H5	120.1	C10i—C10—H10B	109.4
C1—C6—C5	119.19 (14)	H10A—C10—H10B	108.0
C7—N1—N2—C8	−0.54 (19)	C1—C6—C7—S1	6.9 (2)
C6—C1—C2—C3	1.7 (2)	C5—C6—C7—S1	−172.53 (12)
C1—C2—C3—C4	−0.9 (2)	C8—S1—C7—N1	0.48 (12)
C2—C3—C4—C5	0.2 (3)	C8—S1—C7—C6	−179.80 (13)
C3—C4—C5—C6	−0.2 (3)	N1—N2—C8—S1	0.93 (17)
C2—C1—C6—C5	−1.8 (2)	N1—N2—C8—S2	−179.93 (11)
C2—C1—C6—C7	178.80 (14)	C7—S1—C8—N2	−0.81 (13)
C4—C5—C6—C1	1.1 (2)	C7—S1—C8—S2	179.98 (10)
C4—C5—C6—C7	−179.52 (15)	C9—S2—C8—N2	−7.85 (16)
N2—N1—C7—C6	−179.79 (13)	C9—S2—C8—S1	171.26 (9)
N2—N1—C7—S1	−0.08 (17)	C8—S2—C9—C10	−75.00 (13)
C1—C6—C7—N1	−173.44 (15)	S2—C9—C10—C10i	−175.61 (14)
C5—C6—C7—N1	7.2 (2)

Cg is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···Cgii	0.99	2.70	3.540 (2)	144

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯Cgi	0.99	2.70	3.540 (2)	144

Symmetry code: (i) .