5-({3-[(5-Amino-1,3,4-thia-diazol-2-yl)sulfanylmeth-yl]benz-yl}sulfan-yl)-1,3,4-thia-diazol-2-amine.

In the title compound, C(12)H(12)N(6)S(4), the two terminal thia-diazole rings are twisted with respect to the central benzene ring, making dihedral angles of 54.28 (4) and 76.56 (3)°. The dihedral angle between the two thia-diazole rings is 27.77 (4)°. Inter-molecular N-H⋯N hydrogen bonds stabilize the crystal packing, linking the mol-ecules into a tape along the b axis.

Related literature

For the synthesis and reactivity of thia­diazole derivatives, see: Cho et al. (1993 ▶, 2001 ▶) and for the synthesis and reactivity of macrocyclic compounds with thia­diazole derivatives, see: Cho et al. (2002 ▶, 2006 ▶). For related structures of thia­diazole derivatives, see: Kang, Cho & Jang (2012 ▶); Kang, Cho & Jeon (2012 ▶).

Experimental

Crystal data

C12H12N6S4

M = 368.52

Monoclinic,

a = 16.3579 (10) Å

b = 6.1382 (4) Å

c = 30.7095 (18) Å

β = 90.373 (1)°

V = 3083.4 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.62 mm−1

T = 296 K

0.14 × 0.12 × 0.06 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.91, T max = 0.96

22777 measured reflections

3836 independent reflections

2387 reflections with I > 2σ(I)

R int = 0.082

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.077

S = 0.88

3836 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.35 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812013116/is5100sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013116/is5100Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812013116/is5100Isup3.cml

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

C12H12N6S4	F(000) = 1520
Mr = 368.52	Dx = 1.588 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3247 reflections
a = 16.3579 (10) Å	θ = 2.5–22.1°
b = 6.1382 (4) Å	µ = 0.62 mm−1
c = 30.7095 (18) Å	T = 296 K
β = 90.373 (1)°	Block, colourless
V = 3083.4 (3) Å3	0.14 × 0.12 × 0.06 mm
Z = 8

Bruker SMART CCD area-detector diffractometer	2387 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.082
φ and ω scans	θmax = 28.3°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −21→21
Tmin = 0.91, Tmax = 0.96	k = −8→8
22777 measured reflections	l = −40→40
3836 independent 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077	H-atom parameters constrained
S = 0.88	w = 1/[σ2(Fo2) + (0.028P)2] where P = (Fo2 + 2Fc2)/3
3836 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C1	0.07088 (13)	0.5674 (4)	0.54356 (7)	0.0349 (5)
C2	0.04110 (13)	0.4333 (3)	0.57612 (7)	0.0355 (5)
H2	0.0609	0.2917	0.5784	0.043*
C3	−0.01744 (12)	0.5042 (4)	0.60545 (7)	0.0354 (5)
C4	−0.04693 (13)	0.7144 (4)	0.60143 (8)	0.0427 (6)
H4	−0.0857	0.7658	0.6209	0.051*
C5	−0.01915 (14)	0.8485 (4)	0.56860 (8)	0.0462 (6)
H5	−0.0406	0.9881	0.5657	0.055*
C6	0.04010 (14)	0.7777 (4)	0.54005 (7)	0.0428 (6)
H6	0.0594	0.8706	0.5185	0.051*
C7	0.13626 (13)	0.4864 (4)	0.51346 (7)	0.0400 (5)
H7A	0.1306	0.5602	0.4857	0.048*
H7B	0.128	0.332	0.5084	0.048*
S8	0.24002 (3)	0.52863 (9)	0.534089 (19)	0.03947 (16)
C9	0.24017 (12)	0.3680 (3)	0.58115 (7)	0.0327 (5)
S10	0.22830 (4)	0.08693 (9)	0.580246 (18)	0.03689 (15)
C11	0.24370 (12)	0.0940 (4)	0.63625 (7)	0.0324 (5)
N12	0.25717 (11)	0.2911 (3)	0.65155 (6)	0.0376 (4)
N13	0.25390 (10)	0.4480 (3)	0.61950 (6)	0.0357 (4)
N14	0.24306 (11)	−0.0849 (3)	0.66089 (6)	0.0426 (5)
H14A	0.2518	−0.0752	0.6885	0.051*
H14B	0.2339	−0.21	0.6492	0.051*
C15	−0.04979 (13)	0.3540 (4)	0.64040 (7)	0.0430 (6)
H15A	−0.0909	0.2599	0.6274	0.052*
H15B	−0.0766	0.4418	0.6624	0.052*
S16	0.02620 (4)	0.18512 (10)	0.66701 (2)	0.04862 (18)
C17	0.07177 (13)	0.3682 (3)	0.70332 (7)	0.0363 (5)
S18	0.06869 (4)	0.64865 (10)	0.69824 (2)	0.04757 (18)
C19	0.12945 (13)	0.6580 (4)	0.74495 (7)	0.0391 (5)
N20	0.14884 (12)	0.4662 (3)	0.76028 (6)	0.0430 (5)
N21	0.11434 (12)	0.2993 (3)	0.73582 (6)	0.0455 (5)
N22	0.15219 (12)	0.8447 (3)	0.76364 (6)	0.0564 (6)
H22A	0.1812	0.8428	0.7871	0.068*
H22B	0.1378	0.9669	0.7522	0.068*

	U11	U22	U33	U12	U13	U23
C1	0.0349 (12)	0.0417 (14)	0.0280 (12)	−0.0008 (10)	−0.0064 (10)	−0.0027 (10)
C2	0.0362 (12)	0.0349 (13)	0.0352 (13)	0.0035 (10)	−0.0030 (10)	−0.0004 (10)
C3	0.0317 (12)	0.0423 (14)	0.0321 (12)	−0.0024 (10)	−0.0065 (10)	−0.0041 (10)
C4	0.0346 (13)	0.0476 (15)	0.0459 (15)	0.0054 (11)	−0.0044 (11)	−0.0113 (12)
C5	0.0479 (14)	0.0370 (14)	0.0536 (16)	0.0071 (11)	−0.0094 (13)	−0.0018 (12)
C6	0.0462 (14)	0.0424 (15)	0.0396 (14)	−0.0021 (11)	−0.0070 (12)	0.0072 (11)
C7	0.0456 (13)	0.0470 (14)	0.0274 (12)	−0.0006 (11)	−0.0020 (10)	0.0012 (10)
S8	0.0410 (3)	0.0396 (3)	0.0378 (3)	−0.0032 (3)	0.0021 (3)	0.0052 (3)
C9	0.0325 (12)	0.0314 (12)	0.0342 (12)	0.0007 (9)	−0.0004 (10)	−0.0016 (10)
S10	0.0477 (3)	0.0329 (3)	0.0300 (3)	−0.0021 (3)	−0.0028 (3)	−0.0039 (2)
C11	0.0291 (11)	0.0390 (13)	0.0293 (12)	0.0001 (10)	−0.0014 (9)	0.0001 (10)
N12	0.0464 (11)	0.0360 (11)	0.0303 (10)	−0.0010 (9)	−0.0045 (9)	−0.0034 (8)
N13	0.0402 (11)	0.0322 (11)	0.0346 (11)	0.0009 (8)	−0.0033 (9)	−0.0035 (8)
N14	0.0574 (13)	0.0386 (11)	0.0317 (11)	−0.0075 (10)	−0.0053 (9)	0.0026 (9)
C15	0.0394 (13)	0.0529 (15)	0.0368 (13)	−0.0049 (11)	0.0008 (11)	−0.0068 (11)
S16	0.0673 (4)	0.0363 (4)	0.0422 (4)	−0.0041 (3)	−0.0036 (3)	0.0014 (3)
C17	0.0404 (13)	0.0365 (13)	0.0320 (13)	−0.0004 (10)	0.0039 (10)	0.0041 (10)
S18	0.0620 (4)	0.0349 (3)	0.0455 (4)	−0.0020 (3)	−0.0187 (3)	0.0072 (3)
C19	0.0411 (13)	0.0430 (15)	0.0331 (13)	−0.0007 (11)	−0.0043 (10)	0.0065 (11)
N20	0.0550 (13)	0.0369 (12)	0.0370 (11)	0.0018 (10)	−0.0075 (10)	0.0058 (9)
N21	0.0605 (13)	0.0370 (12)	0.0389 (12)	0.0034 (10)	−0.0054 (10)	0.0045 (9)
N22	0.0771 (16)	0.0392 (12)	0.0525 (14)	−0.0017 (11)	−0.0322 (12)	0.0058 (10)

C1—C2	1.386 (3)	S10—C11	1.737 (2)
C1—C6	1.390 (3)	C11—N12	1.316 (3)
C1—C7	1.503 (3)	C11—N14	1.334 (3)
C2—C3	1.389 (3)	N12—N13	1.378 (2)
C2—H2	0.93	N14—H14A	0.86
C3—C4	1.383 (3)	N14—H14B	0.86
C3—C15	1.513 (3)	C15—S16	1.810 (2)
C4—C5	1.381 (3)	C15—H15A	0.97
C4—H4	0.93	C15—H15B	0.97
C5—C6	1.381 (3)	S16—C17	1.747 (2)
C5—H5	0.93	C17—N21	1.285 (3)
C6—H6	0.93	C17—S18	1.729 (2)
C7—S8	1.826 (2)	S18—C19	1.741 (2)
C7—H7A	0.97	C19—N20	1.306 (3)
C7—H7B	0.97	C19—N22	1.333 (3)
S8—C9	1.749 (2)	N20—N21	1.388 (2)
C9—N13	1.294 (2)	N22—H22A	0.86
C9—S10	1.737 (2)	N22—H22B	0.86
C2—C1—C6	118.6 (2)	C9—S10—C11	86.78 (10)
C2—C1—C7	120.16 (19)	N12—C11—N14	123.81 (19)
C6—C1—C7	121.2 (2)	N12—C11—S10	113.52 (16)
C1—C2—C3	121.9 (2)	N14—C11—S10	122.66 (17)
C1—C2—H2	119	C11—N12—N13	112.45 (17)
C3—C2—H2	119	C9—N13—N12	113.00 (17)
C4—C3—C2	118.4 (2)	C11—N14—H14A	120
C4—C3—C15	120.6 (2)	C11—N14—H14B	120
C2—C3—C15	121.0 (2)	H14A—N14—H14B	120
C5—C4—C3	120.3 (2)	C3—C15—S16	115.29 (15)
C5—C4—H4	119.8	C3—C15—H15A	108.5
C3—C4—H4	119.8	S16—C15—H15A	108.5
C4—C5—C6	120.8 (2)	C3—C15—H15B	108.5
C4—C5—H5	119.6	S16—C15—H15B	108.5
C6—C5—H5	119.6	H15A—C15—H15B	107.5
C5—C6—C1	119.9 (2)	C17—S16—C15	102.05 (11)
C5—C6—H6	120	N21—C17—S18	114.41 (17)
C1—C6—H6	120	N21—C17—S16	120.73 (17)
C1—C7—S8	113.78 (15)	S18—C17—S16	124.80 (13)
C1—C7—H7A	108.8	C17—S18—C19	86.69 (11)
S8—C7—H7A	108.8	N20—C19—N22	123.6 (2)
C1—C7—H7B	108.8	N20—C19—S18	113.79 (17)
S8—C7—H7B	108.8	N22—C19—S18	122.63 (17)
H7A—C7—H7B	107.7	C19—N20—N21	111.92 (18)
C9—S8—C7	101.71 (10)	C17—N21—N20	113.17 (18)
N13—C9—S10	114.22 (16)	C19—N22—H22A	120
N13—C9—S8	122.50 (16)	C19—N22—H22B	120
S10—C9—S8	123.17 (12)	H22A—N22—H22B	120

D—H···A	D—H	H···A	D···A	D—H···A
N14—H14A···N20i	0.86	2.27	3.005 (3)	144
N14—H14B···N13ii	0.86	2.31	3.142 (2)	162
N22—H22A···N12iii	0.86	2.15	3.007 (3)	171
N22—H22B···N21iv	0.86	2.14	2.982 (3)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N14—H14A⋯N20i	0.86	2.27	3.005 (3)	144
N14—H14B⋯N13ii	0.86	2.31	3.142 (2)	162
N22—H22A⋯N12iii	0.86	2.15	3.007 (3)	171
N22—H22B⋯N21iv	0.86	2.14	2.982 (3)	168

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .