5,5'-[(1,4-Phenyl-enedimethyl-ene)bis-(sulfanedi-yl)]bis-(1-methyl-1H-1,2,3,4-tetra-zole).

The title mol-ecule, C(12)H(14)N(8)S(2), has point symmetry [Formula: see text] since it is situated on a crystallographic centre of symmetry. The 1-meth-yl/5-thio groups are in an anti-periplanar conformation. The dihedral angle between the benzene and tetra-zole rings is 84.33 (2)°. In the crystal, C-H⋯N hydrogen bonds link mol-ecules into ladder-like chains running along the b axis. There are also C-H⋯π inter-actions present in the crystal structure.

Related literature

For the pharmaceutical properties of ligands derived from tetra­zole, see: Armour et al. (1996 ▶); Segarra et al. (1998 ▶); Bronisz (2002 ▶); Semenov (2002 ▶); Upadhayaya et al. (2004 ▶); Wang et al. (2004 ▶); She et al. (2006 ▶); Wei et al. (2011 ▶). For the synthesis of the title compound, see: Wang et al. (2005 ▶). For graph-set motifs, see: Etter et al. (1990 ▶).

Experimental

Crystal data

C12H14N8S2

M = 334.43

Monoclinic,

a = 18.464 (4) Å

b = 7.6392 (18) Å

c = 13.625 (3) Å

β = 126.999 (4)°

V = 1534.8 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.36 mm−1

T = 296 K

0.25 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.916, T max = 0.965

6541 measured reflections

1758 independent reflections

1412 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.116

S = 1.07

1758 reflections

101 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811043182/fb2238sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811043182/fb2238Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811043182/fb2238Isup3.cml

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

C12H14N8S2	F(000) = 696
Mr = 334.43	Dx = 1.447 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2201 reflections
a = 18.464 (4) Å	θ = 3.0–26.9°
b = 7.6392 (18) Å	µ = 0.36 mm−1
c = 13.625 (3) Å	T = 296 K
β = 126.999 (4)°	Block, colorless
V = 1534.8 (6) Å3	0.25 × 0.10 × 0.10 mm
Z = 4

Bruker SMART APEXII diffractometer	1758 independent reflections
Radiation source: fine-focus sealed tube	1412 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 27.6°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −19→24
Tmin = 0.916, Tmax = 0.965	k = −9→9
6541 measured reflections	l = −17→15

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)] = 0.040	Hydrogen site location: difference Fourier map
wR(F2) = 0.116	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0582P)2 + 0.9815P] where P = (Fo2 + 2Fc2)/3
1758 reflections	(Δ/σ)max < 0.001
101 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.26 e Å−3
27 constraints

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	0.15096 (4)	0.07607 (7)	0.36393 (5)	0.04497 (19)
N1	0.16911 (15)	0.3872 (3)	0.27877 (19)	0.0558 (5)
N2	0.15595 (18)	0.5580 (3)	0.2902 (2)	0.0697 (6)
N3	0.12550 (16)	0.5769 (3)	0.3536 (2)	0.0652 (6)
N4	0.11760 (12)	0.4145 (2)	0.38467 (16)	0.0452 (4)
C1	−0.07348 (14)	−0.1014 (3)	−0.03169 (19)	0.0413 (5)
H1	−0.1225	−0.1697	−0.0523	0.050*
C2	0.00541 (14)	−0.1013 (3)	0.08832 (19)	0.0413 (4)
H2	0.0087	−0.1696	0.1474	0.050*
C3	0.07963 (13)	0.0003 (3)	0.12106 (17)	0.0384 (4)
C4	0.16597 (14)	−0.0016 (3)	0.25088 (19)	0.0444 (5)
H4A	0.2107	0.0712	0.2549	0.053*
H4B	0.1894	−0.1202	0.2718	0.053*
C5	0.14563 (12)	0.2996 (3)	0.33927 (16)	0.0390 (4)
C6	0.08800 (19)	0.3838 (4)	0.4606 (3)	0.0640 (7)
H6A	0.0387	0.3017	0.4203	0.096*
H6B	0.0683	0.4921	0.4731	0.096*
H6C	0.1375	0.3371	0.5385	0.096*

	U11	U22	U33	U12	U13	U23
S1	0.0542 (3)	0.0439 (3)	0.0376 (3)	−0.0049 (2)	0.0280 (2)	−0.0001 (2)
N1	0.0711 (13)	0.0491 (11)	0.0643 (12)	−0.0057 (9)	0.0497 (11)	0.0038 (9)
N2	0.0895 (17)	0.0488 (12)	0.0893 (17)	−0.0011 (11)	0.0636 (15)	0.0105 (11)
N3	0.0751 (14)	0.0451 (12)	0.0819 (16)	0.0064 (10)	0.0507 (14)	0.0054 (10)
N4	0.0409 (9)	0.0459 (10)	0.0497 (10)	0.0017 (7)	0.0278 (8)	0.0002 (8)
C1	0.0418 (10)	0.0438 (11)	0.0449 (11)	−0.0055 (8)	0.0296 (9)	−0.0073 (8)
C2	0.0474 (11)	0.0421 (11)	0.0411 (10)	−0.0026 (9)	0.0303 (9)	−0.0021 (8)
C3	0.0387 (10)	0.0404 (10)	0.0391 (10)	−0.0002 (8)	0.0250 (8)	−0.0078 (8)
C4	0.0408 (10)	0.0467 (12)	0.0445 (11)	0.0022 (9)	0.0250 (9)	−0.0040 (9)
C5	0.0336 (9)	0.0449 (11)	0.0335 (9)	−0.0040 (8)	0.0176 (8)	−0.0014 (8)
C6	0.0681 (16)	0.0732 (17)	0.0717 (17)	−0.0009 (13)	0.0532 (15)	−0.0078 (13)

S1—C5	1.732 (2)	C1—H1	0.9300
S1—C4	1.821 (2)	C2—C3	1.394 (3)
N1—C5	1.321 (3)	C2—H2	0.9300
N1—N2	1.353 (3)	C3—C1i	1.388 (3)
N2—N3	1.291 (3)	C3—C4	1.509 (3)
N3—N4	1.347 (3)	C4—H4A	0.9700
N4—C5	1.344 (3)	C4—H4B	0.9700
N4—C6	1.450 (3)	C6—H6A	0.9600
C1—C3i	1.388 (3)	C6—H6B	0.9600
C1—C2	1.389 (3)	C6—H6C	0.9600
C5—S1—C4	100.20 (10)	C3—C4—S1	113.41 (14)
C5—N1—N2	105.50 (19)	C3—C4—H4A	108.9
N3—N2—N1	111.44 (19)	S1—C4—H4A	108.9
N2—N3—N4	106.27 (19)	C3—C4—H4B	108.9
C5—N4—N3	108.20 (18)	S1—C4—H4B	108.9
C5—N4—C6	129.58 (19)	H4A—C4—H4B	107.7
N3—N4—C6	122.13 (19)	N1—C5—N4	108.57 (19)
C3i—C1—C2	120.44 (18)	N1—C5—S1	128.22 (17)
C3i—C1—H1	119.8	N4—C5—S1	123.19 (15)
C2—C1—H1	119.8	N4—C6—H6A	109.5
C1—C2—C3	120.64 (18)	N4—C6—H6B	109.5
C1—C2—H2	119.7	H6A—C6—H6B	109.5
C3—C2—H2	119.7	N4—C6—H6C	109.5
C1i—C3—C2	118.92 (18)	H6A—C6—H6C	109.5
C1i—C3—C4	120.31 (18)	H6B—C6—H6C	109.5
C2—C3—C4	120.77 (18)
C5—N1—N2—N3	−0.3 (3)	C5—S1—C4—C3	−76.96 (17)
N1—N2—N3—N4	−0.4 (3)	N2—N1—C5—N4	0.9 (2)
N2—N3—N4—C5	0.9 (3)	N2—N1—C5—S1	−177.38 (17)
N2—N3—N4—C6	177.8 (2)	N3—N4—C5—N1	−1.2 (2)
C3i—C1—C2—C3	0.0 (3)	C6—N4—C5—N1	−177.7 (2)
C1—C2—C3—C1i	0.0 (3)	N3—N4—C5—S1	177.23 (15)
C1—C2—C3—C4	−178.97 (18)	C6—N4—C5—S1	0.6 (3)
C1i—C3—C4—S1	119.20 (18)	C4—S1—C5—N1	−15.1 (2)
C2—C3—C4—S1	−61.8 (2)	C4—S1—C5—N4	166.87 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4B···N2ii	0.97	2.58	3.429 (3)	145
C6—H6A···Cgbenzeneiii	0.96	2.82	3.545 (4)	133

Table 1

Hydrogen-bond geometry (Å, °)

Cg benzene is the centroid of the benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4B⋯N2i	0.97	2.58	3.429 (3)	145
C6—H6A⋯Cgbenzeneii	0.96	2.82	3.545 (4)	133

Symmetry codes: (i) ; (ii) .