N,N'-Bis(1,3-thia-zol-2-yl)methyl-ene-diamine.

In the title compound, C(7)H(8)N(4)S(2), the dihedral angle between the thia-zoline rings is 71.25 (13)°. In the crystal, inter-molecular N-H⋯N hydrogen bonds connect the mol-ecules into zigzag chains parallel to the ab plane.

Related literature

For applications of thia­zole compounds see: Raman et al. (2000 ▶); Karimian (2009 ▶); Shi et al. (1996 ▶). For related structures containing an amino­thia­zole moiety, see: Odabaşoğlu & Büyükgüngör, (2006 ▶); Zhao et al. (2006 ▶).

Experimental

Crystal data

C7H8N4S2

M = 212.31

Monoclinic,

a = 7.8598 (16) Å

b = 8.9291 (18) Å

c = 13.672 (3) Å

β = 96.39 (3)°

V = 953.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.52 mm−1

T = 298 K

0.45 × 0.35 × 0.3 mm

Data collection

Stoe IPDS 2T diffractometer

7352 measured reflections

2551 independent reflections

1544 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.162

S = 1.10

2551 reflections

126 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.33 e Å−3

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811047659/bt5707sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811047659/bt5707Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811047659/bt5707Isup3.cml

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

C7H8N4S2	F(000) = 440
Mr = 212.31	Dx = 1.479 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2551 reflections
a = 7.8598 (16) Å	θ = 2.9–29.2°
b = 8.9291 (18) Å	µ = 0.52 mm−1
c = 13.672 (3) Å	T = 298 K
β = 96.39 (3)°	Block, colorless
V = 953.6 (3) Å3	0.45 × 0.35 × 0.3 mm
Z = 4

Stoe IPDS 2T diffractometer	1544 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.055
graphite	θmax = 29.2°, θmin = 2.9°
Detector resolution: 0.15 mm pixels mm-1	h = −10→10
rotation method scans	k = −10→12
7352 measured reflections	l = −18→16
2551 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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.0781P)2] where P = (Fo2 + 2Fc2)/3
2551 reflections	(Δ/σ)max < 0.001
126 parameters	Δρmax = 0.35 e Å−3
2 restraints	Δρmin = −0.33 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	0.17187 (10)	0.85527 (11)	0.66273 (7)	0.0600 (3)
S2	0.38487 (10)	0.58898 (11)	0.36382 (7)	0.0638 (3)
N2	0.2786 (3)	0.9024 (3)	0.4824 (2)	0.0534 (7)
N3	0.1223 (3)	0.6689 (3)	0.4651 (2)	0.0517 (7)
N4	0.1924 (3)	0.4157 (3)	0.4539 (2)	0.0503 (6)
C1	0.3071 (4)	0.9249 (3)	0.5804 (2)	0.0458 (7)
C5	0.2187 (3)	0.5568 (3)	0.4343 (2)	0.0445 (6)
N1	0.4391 (3)	0.9984 (3)	0.6235 (2)	0.0540 (7)
C3	0.4335 (4)	1.0032 (4)	0.7244 (3)	0.0609 (9)
H3	0.5177	1.0521	0.7658	0.073*
C4	0.1332 (4)	0.8213 (4)	0.4347 (3)	0.0543 (8)
H4A	0.0294	0.8727	0.4476	0.065*
H4B	0.1386	0.8234	0.3642	0.065*
C6	0.3067 (4)	0.3273 (4)	0.4103 (3)	0.0596 (9)
H6	0.3066	0.2236	0.4161	0.072*
C2	0.3025 (4)	0.9349 (5)	0.7596 (3)	0.0663 (10)
H2	0.2841	0.9306	0.8255	0.080*
C7	0.4177 (4)	0.3987 (4)	0.3592 (3)	0.0637 (9)
H7	0.5004	0.3523	0.3261	0.076*
H3A	0.031 (3)	0.645 (4)	0.489 (2)	0.053 (9)*
H2A	0.358 (4)	0.924 (5)	0.447 (3)	0.084 (13)*

	U11	U22	U33	U12	U13	U23
S1	0.0549 (4)	0.0643 (6)	0.0650 (5)	−0.0030 (4)	0.0247 (4)	0.0069 (4)
S2	0.0533 (5)	0.0637 (6)	0.0801 (6)	−0.0071 (4)	0.0333 (4)	−0.0008 (5)
N2	0.0617 (15)	0.0475 (16)	0.0529 (16)	−0.0179 (12)	0.0145 (12)	0.0007 (12)
N3	0.0445 (13)	0.0392 (15)	0.0749 (18)	−0.0073 (10)	0.0228 (12)	−0.0046 (12)
N4	0.0464 (13)	0.0423 (15)	0.0648 (17)	−0.0020 (10)	0.0173 (11)	0.0001 (12)
C1	0.0502 (15)	0.0326 (15)	0.0568 (18)	0.0012 (11)	0.0156 (13)	0.0033 (13)
C5	0.0365 (12)	0.0482 (17)	0.0498 (16)	−0.0050 (11)	0.0098 (11)	−0.0066 (14)
N1	0.0539 (15)	0.0482 (16)	0.0615 (16)	−0.0081 (11)	0.0131 (12)	−0.0041 (13)
C3	0.0624 (19)	0.066 (2)	0.0543 (19)	0.0030 (16)	0.0080 (15)	−0.0124 (16)
C4	0.0527 (16)	0.0458 (18)	0.065 (2)	−0.0034 (13)	0.0072 (14)	0.0001 (15)
C6	0.0561 (16)	0.0466 (19)	0.078 (2)	0.0090 (14)	0.0169 (15)	−0.0049 (17)
C2	0.067 (2)	0.084 (3)	0.0508 (19)	0.0105 (18)	0.0172 (16)	−0.0026 (18)
C7	0.0522 (17)	0.067 (2)	0.075 (2)	0.0116 (15)	0.0218 (16)	−0.0061 (18)

S1—C2	1.735 (4)	N4—C6	1.380 (4)
S1—C1	1.746 (3)	C1—N1	1.311 (4)
S2—C7	1.721 (4)	N1—C3	1.385 (5)
S2—C5	1.731 (3)	C3—C2	1.332 (5)
N2—C1	1.349 (4)	C3—H3	0.9300
N2—C4	1.446 (4)	C4—H4A	0.9700
N2—H2A	0.850 (19)	C4—H4B	0.9700
N3—C5	1.351 (4)	C6—C7	1.338 (5)
N3—C4	1.428 (4)	C6—H6	0.9300
N3—H3A	0.850 (18)	C2—H2	0.9300
N4—C5	1.309 (4)	C7—H7	0.9300
C2—S1—C1	89.70 (17)	C2—C3—H3	121.4
C7—S2—C5	88.96 (16)	N1—C3—H3	121.4
C1—N2—C4	123.9 (3)	N3—C4—N2	114.6 (3)
C1—N2—H2A	118 (3)	N3—C4—H4A	108.6
C4—N2—H2A	117 (3)	N2—C4—H4A	108.6
C5—N3—C4	124.1 (3)	N3—C4—H4B	108.6
C5—N3—H3A	117 (2)	N2—C4—H4B	108.6
C4—N3—H3A	116 (2)	H4A—C4—H4B	107.6
C5—N4—C6	109.7 (3)	C7—C6—N4	116.5 (3)
N1—C1—N2	123.8 (3)	C7—C6—H6	121.7
N1—C1—S1	113.4 (2)	N4—C6—H6	121.7
N2—C1—S1	122.8 (2)	C3—C2—S1	109.1 (3)
N4—C5—N3	122.8 (2)	C3—C2—H2	125.4
N4—C5—S2	114.8 (2)	S1—C2—H2	125.4
N3—C5—S2	122.3 (2)	C6—C7—S2	110.0 (2)
C1—N1—C3	110.6 (3)	C6—C7—H7	125.0
C2—C3—N1	117.2 (3)	S2—C7—H7	125.0
C4—N2—C1—N1	179.9 (3)	N2—C1—N1—C3	179.9 (3)
C4—N2—C1—S1	1.1 (4)	S1—C1—N1—C3	−1.1 (3)
C2—S1—C1—N1	1.1 (3)	C1—N1—C3—C2	0.5 (5)
C2—S1—C1—N2	−179.9 (3)	C5—N3—C4—N2	−77.4 (4)
C6—N4—C5—N3	178.0 (3)	C1—N2—C4—N3	−60.5 (4)
C6—N4—C5—S2	−0.9 (4)	C5—N4—C6—C7	0.3 (5)
C4—N3—C5—N4	−171.6 (3)	N1—C3—C2—S1	0.3 (4)
C4—N3—C5—S2	7.2 (5)	C1—S1—C2—C3	−0.8 (3)
C7—S2—C5—N4	1.0 (3)	N4—C6—C7—S2	0.4 (5)
C7—S2—C5—N3	−177.9 (3)	C5—S2—C7—C6	−0.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1i	0.85 (2)	2.07 (2)	2.918 (4)	171 (4)
N3—H3A···N4ii	0.85 (2)	2.07 (2)	2.919 (3)	179 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N1i	0.85 (2)	2.07 (2)	2.918 (4)	171 (4)
N3—H3A⋯N4ii	0.85 (2)	2.07 (2)	2.919 (3)	179 (4)

Symmetry codes: (i) ; (ii) .