5-(Thio-phen-2-ylmeth-yl)-1,3,4-thia-diazol-2-amine.

In the title mol-ecule, C(7)H(7)N(3)S(2), the dihedral angle between the thio-phene and thia-diazole rings is 72.99 (5)°; the two rings are oriented so that the S atoms in each ring are on the same side. In the crystal, the three-dimensional network involves strong N-H⋯O hydrogen bonds, as well as C-H⋯π and π-π stacking inter-actions [centroid-centroid distances = 3.654 (1) and 3.495 (1) Å].

Related literature

For the anti­tumor activity of 2-amino-1,3,4-thia­diazole, 2-ethyl­amino-1,3,4-thia­diazole and 2,2′-(methyl­enediamino)­bis-1,3,4-thia­diazole, see: Olesan et al. (1955 ▶); Mishra et al. (1995 ▶). For their anti-HIV, anti­proliferative, germicidal and D2 dopamine­rgic activity, see: Mohareb et al. (2004 ▶). For the synthesis of the title compound, see: Sancak et al., (2007 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C7H7N3S2

M = 197.28

Monoclinic,

a = 11.2970 (6) Å

b = 6.6094 (3) Å

c = 11.2480 (6) Å

β = 97.243 (5)°

V = 833.15 (7) Å3

Z = 4

Cu Kα radiation

μ = 5.33 mm−1

T = 173 K

0.46 × 0.28 × 0.15 mm

Data collection

Agilent Xcalibur Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.209, T max = 0.450

4375 measured reflections

1539 independent reflections

1497 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.120

S = 1.09

1539 reflections

110 parameters

H-atom parameters constrained

Δρmax = 0.64 e Å−3

Δρmin = −0.38 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 datablock(s) I, global. DOI: 10.1107/S1600536812013633/hg5202sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013633/hg5202Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812013633/hg5202Isup3.cml

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

C7H7N3S2	F(000) = 408
Mr = 197.28	Dx = 1.573 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 2744 reflections
a = 11.2970 (6) Å	θ = 3.9–70.0°
b = 6.6094 (3) Å	µ = 5.33 mm−1
c = 11.2480 (6) Å	T = 173 K
β = 97.243 (5)°	Chunk, colorless
V = 833.15 (7) Å3	0.46 × 0.28 × 0.15 mm
Z = 4

Agilent Xcalibur Eos Gemini diffractometer	1539 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1497 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
Detector resolution: 16.1500 pixels mm-1	θmax = 70.1°, θmin = 3.9°
ω scans	h = −13→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −5→8
Tmin = 0.209, Tmax = 0.450	l = −12→13
4375 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045	H-atom parameters constrained
wR(F2) = 0.120	w = 1/[σ2(Fo2) + (0.0928P)2 + 0.0849P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.001
1539 reflections	Δρmax = 0.64 e Å−3
110 parameters	Δρmin = −0.38 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.035 (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	0.64166 (4)	0.57641 (7)	0.32224 (4)	0.0210 (2)
S2	0.82410 (4)	1.05521 (6)	0.34150 (3)	0.0182 (2)
N1	0.87197 (12)	1.0981 (2)	0.56747 (13)	0.0175 (4)
N2	0.91662 (12)	1.2714 (2)	0.51908 (13)	0.0179 (4)
N3	0.93579 (14)	1.4168 (2)	0.33358 (14)	0.0251 (4)
H3A	0.9732	1.5198	0.3665	0.030*
H3B	0.9220	1.4085	0.2568	0.030*
C1	0.48911 (16)	0.5889 (3)	0.30609 (17)	0.0216 (4)
H1	0.4395	0.5306	0.2430	0.026*
C2	0.44958 (15)	0.6943 (3)	0.39653 (16)	0.0226 (4)
H2	0.3693	0.7160	0.4030	0.027*
C3	0.54422 (16)	0.7680 (3)	0.48045 (16)	0.0206 (4)
H3	0.5323	0.8420	0.5483	0.025*
C4	0.65455 (15)	0.7192 (2)	0.45147 (15)	0.0171 (4)
C5	0.77380 (16)	0.7709 (3)	0.51957 (16)	0.0212 (4)
H5A	0.8306	0.6668	0.5044	0.025*
H5B	0.7667	0.7689	0.6046	0.025*
C6	0.82264 (14)	0.9732 (3)	0.48849 (14)	0.0159 (4)
C7	0.89906 (14)	1.2698 (3)	0.40174 (15)	0.0165 (4)

	U11	U22	U33	U12	U13	U23
S1	0.0161 (3)	0.0215 (4)	0.0250 (4)	−0.00005 (14)	0.0010 (2)	−0.00692 (15)
S2	0.0184 (3)	0.0192 (3)	0.0158 (3)	−0.00404 (13)	−0.0027 (2)	−0.00264 (13)
N1	0.0172 (7)	0.0156 (7)	0.0191 (7)	−0.0010 (5)	0.0000 (6)	0.0004 (5)
N2	0.0170 (7)	0.0175 (8)	0.0184 (7)	−0.0032 (5)	−0.0012 (5)	−0.0010 (5)
N3	0.0272 (9)	0.0290 (9)	0.0172 (8)	−0.0138 (6)	−0.0039 (6)	0.0017 (6)
C1	0.0172 (8)	0.0152 (8)	0.0311 (9)	−0.0020 (6)	−0.0017 (7)	0.0002 (7)
C2	0.0176 (8)	0.0169 (9)	0.0337 (10)	0.0024 (6)	0.0052 (7)	0.0078 (7)
C3	0.0248 (9)	0.0135 (9)	0.0239 (9)	0.0041 (6)	0.0054 (7)	0.0012 (6)
C4	0.0211 (8)	0.0084 (8)	0.0213 (9)	−0.0011 (6)	0.0007 (7)	0.0000 (6)
C5	0.0236 (9)	0.0130 (9)	0.0251 (9)	−0.0007 (6)	−0.0039 (7)	0.0016 (7)
C6	0.0139 (7)	0.0152 (8)	0.0179 (8)	0.0022 (6)	−0.0004 (6)	−0.0003 (6)
C7	0.0100 (7)	0.0184 (9)	0.0199 (8)	−0.0002 (6)	−0.0025 (6)	−0.0031 (6)

S1—C1	1.7119 (18)	C1—C2	1.354 (3)
S1—C4	1.7237 (17)	C1—H1	0.9300
S2—C6	1.7419 (17)	C2—C3	1.420 (3)
S2—C7	1.7445 (17)	C2—H2	0.9300
N1—C6	1.287 (2)	C3—C4	1.366 (2)
N1—N2	1.390 (2)	C3—H3	0.9300
N2—C7	1.310 (2)	C4—C5	1.503 (2)
N3—C7	1.336 (2)	C5—C6	1.505 (2)
N3—H3A	0.8600	C5—H5A	0.9700
N3—H3B	0.8600	C5—H5B	0.9700
C1—S1—C4	92.29 (9)	C3—C4—C5	127.66 (16)
C6—S2—C7	86.93 (8)	C3—C4—S1	110.36 (13)
C6—N1—N2	113.90 (14)	C5—C4—S1	121.96 (13)
C7—N2—N1	111.83 (14)	C4—C5—C6	114.53 (14)
C7—N3—H3A	120.0	C4—C5—H5A	108.6
C7—N3—H3B	120.0	C6—C5—H5A	108.6
H3A—N3—H3B	120.0	C4—C5—H5B	108.6
C2—C1—S1	111.59 (14)	C6—C5—H5B	108.6
C2—C1—H1	124.2	H5A—C5—H5B	107.6
S1—C1—H1	124.2	N1—C6—C5	123.32 (15)
C1—C2—C3	112.57 (16)	N1—C6—S2	113.61 (13)
C1—C2—H2	123.7	C5—C6—S2	123.00 (12)
C3—C2—H2	123.7	N2—C7—N3	123.65 (16)
C4—C3—C2	113.16 (16)	N2—C7—S2	113.71 (13)
C4—C3—H3	123.4	N3—C7—S2	122.63 (13)
C2—C3—H3	123.4
C6—N1—N2—C7	−0.27 (19)	N2—N1—C6—C5	176.73 (15)
C4—S1—C1—C2	−1.08 (14)	N2—N1—C6—S2	−0.36 (18)
S1—C1—C2—C3	0.4 (2)	C4—C5—C6—N1	136.56 (17)
C1—C2—C3—C4	0.7 (2)	C4—C5—C6—S2	−46.6 (2)
C2—C3—C4—C5	−179.68 (15)	C7—S2—C6—N1	0.64 (13)
C2—C3—C4—S1	−1.50 (19)	C7—S2—C6—C5	−176.45 (15)
C1—S1—C4—C3	1.47 (14)	N1—N2—C7—N3	−178.55 (16)
C1—S1—C4—C5	179.78 (14)	N1—N2—C7—S2	0.78 (18)
C3—C4—C5—C6	−87.1 (2)	C6—S2—C7—N2	−0.80 (13)
S1—C4—C5—C6	94.86 (17)	C6—S2—C7—N3	178.53 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···N1i	0.86	2.13	2.991 (2)	175
N3—H3A···N2ii	0.86	2.17	3.013 (2)	167
C1—H1···Cgiii	0.93	2.83	3.549 (2)	135

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the S1/C1–C4 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3B⋯N1i	0.86	2.13	2.991 (2)	175
N3—H3A⋯N2ii	0.86	2.17	3.013 (2)	167
C1—H1⋯Cgiii	0.93	2.83	3.549 (2)	135

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