1,3-Benzothia-zol-2-amine.

In the crystal structure of the title compound, C(7)H(6)N(2)S, mol-ecules related by an inversion center are linked via N-H⋯N hydrogen bonds involving the amino groups, forming dimers. In turn, these dimers are linked via a second N-H⋯N hydrogen bond, forming an infinite two-dimensional network parallel to (011).

Related literature

For the original powder diffraction study of the title compound, see: Goubitz et al. (2001 ▶). For related structures containing the title compound, see: Martínez-Martínez et al. (2003 ▶); Padilla-Martínez et al. (2003 ▶); Wang et al. (2008 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C7H6N2S

M = 150.20

Monoclinic,

a = 14.606 (4) Å

b = 3.997 (1) Å

c = 11.565 (4) Å

β = 94.47 (2)°

V = 673.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.39 mm−1

T = 173 K

0.50 × 0.50 × 0.50 mm

Data collection

Stoe IPDS-2 diffractometer

Absorption correction: none

2783 measured reflections

1181 independent reflections

1061 reflections with I > 2σ(I)

R int = 0.086

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.143

S = 1.06

1181 reflections

99 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.31 e Å−3

Data collection: X-AREA (Stoe & Cie, 2006 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2006 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809027561/jh2090sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027561/jh2090Isup2.hkl

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

C7H6N2S	F(000) = 312
Mr = 150.20	Dx = 1.482 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 42133 reflections
a = 14.606 (4) Å	θ = 3.5–25.6°
b = 3.997 (1) Å	µ = 0.39 mm−1
c = 11.565 (4) Å	T = 173 K
β = 94.47 (2)°	Block, colourless
V = 673.1 (3) Å3	0.50 × 0.50 × 0.50 mm
Z = 4

Stoe IPDS-2 diffractometer	1061 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.086
graphite	θmax = 25.2°, θmin = 3.5°
φ and ω scans	h = −17→15
2783 measured reflections	k = −4→4
1181 independent reflections	l = −13→13

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.1031P)2 + 0.0494P] where P = (Fo2 + 2Fc2)/3
1181 reflections	(Δ/σ)max < 0.001
99 parameters	Δρmax = 0.38 e Å−3
2 restraints	Δρmin = −0.31 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.17155 (4)	0.19806 (15)	0.24812 (4)	0.0406 (3)
N1	0.12810 (12)	0.4914 (5)	0.04966 (13)	0.0373 (5)
N2	0.00290 (14)	0.2707 (6)	0.14135 (17)	0.0427 (7)
C1	0.25983 (15)	0.3777 (6)	0.17558 (17)	0.0391 (7)
C2	0.35252 (17)	0.3886 (7)	0.2091 (2)	0.0481 (8)
C3	0.40994 (17)	0.5406 (7)	0.1364 (2)	0.0523 (8)
C4	0.37475 (18)	0.6870 (6)	0.0321 (2)	0.0492 (8)
C5	0.28136 (17)	0.6797 (6)	−0.0011 (2)	0.0435 (7)
C6	0.22260 (15)	0.5222 (5)	0.07108 (17)	0.0381 (6)
C7	0.09342 (15)	0.3274 (5)	0.13327 (18)	0.0367 (7)
H2	0.37610	0.29340	0.28060	0.0580*
H2A	−0.009 (2)	0.116 (6)	0.182 (2)	0.062 (9)*
H2B	−0.0377 (18)	0.328 (7)	0.091 (2)	0.063 (9)*
H3	0.47420	0.54640	0.15710	0.0630*
H4	0.41550	0.79300	−0.01660	0.0590*
H5	0.25790	0.78020	−0.07170	0.0520*

	U11	U22	U33	U12	U13	U23
S1	0.0458 (5)	0.0516 (5)	0.0240 (4)	0.0062 (2)	0.0010 (3)	0.0025 (2)
N1	0.0421 (10)	0.0481 (10)	0.0218 (8)	0.0010 (8)	0.0038 (7)	−0.0002 (7)
N2	0.0419 (11)	0.0582 (12)	0.0282 (11)	−0.0013 (9)	0.0048 (8)	0.0087 (8)
C1	0.0429 (12)	0.0467 (11)	0.0278 (11)	0.0062 (9)	0.0038 (9)	−0.0062 (8)
C2	0.0472 (13)	0.0581 (14)	0.0376 (12)	0.0064 (11)	−0.0050 (10)	−0.0080 (10)
C3	0.0391 (12)	0.0645 (16)	0.0526 (15)	0.0011 (11)	−0.0001 (11)	−0.0144 (12)
C4	0.0458 (14)	0.0573 (15)	0.0456 (14)	−0.0084 (10)	0.0103 (11)	−0.0114 (10)
C5	0.0454 (13)	0.0546 (14)	0.0310 (11)	−0.0034 (10)	0.0067 (9)	−0.0056 (9)
C6	0.0443 (12)	0.0456 (11)	0.0242 (10)	0.0010 (9)	0.0023 (8)	−0.0057 (8)
C7	0.0425 (12)	0.0459 (13)	0.0215 (10)	0.0039 (9)	0.0017 (9)	−0.0031 (8)

S1—C1	1.747 (2)	C2—C3	1.375 (4)
S1—C7	1.760 (2)	C3—C4	1.402 (3)
N1—C6	1.389 (3)	C4—C5	1.388 (4)
N1—C7	1.303 (3)	C5—C6	1.393 (3)
N2—C7	1.352 (3)	C2—H2	0.9500
N2—H2B	0.83 (2)	C3—H3	0.9500
N2—H2A	0.80 (2)	C4—H4	0.9500
C1—C6	1.410 (3)	C5—H5	0.9500
C1—C2	1.380 (3)
C1—S1—C7	88.64 (10)	N1—C6—C1	115.36 (18)
C6—N1—C7	110.53 (17)	N1—C6—C5	125.68 (19)
H2A—N2—H2B	117 (3)	S1—C7—N1	116.18 (16)
C7—N2—H2B	123.7 (18)	S1—C7—N2	118.60 (16)
C7—N2—H2A	115 (2)	N1—C7—N2	125.1 (2)
C2—C1—C6	122.2 (2)	C1—C2—H2	121.00
S1—C1—C6	109.29 (16)	C3—C2—H2	121.00
S1—C1—C2	128.54 (17)	C2—C3—H3	120.00
C1—C2—C3	118.3 (2)	C4—C3—H3	120.00
C2—C3—C4	120.7 (2)	C3—C4—H4	119.00
C3—C4—C5	121.0 (2)	C5—C4—H4	120.00
C4—C5—C6	118.8 (2)	C4—C5—H5	121.00
C1—C6—C5	119.0 (2)	C6—C5—H5	121.00
C7—S1—C1—C2	−179.8 (2)	S1—C1—C6—N1	0.0 (2)
C7—S1—C1—C6	0.41 (17)	S1—C1—C6—C5	−179.83 (17)
C1—S1—C7—N1	−0.79 (18)	C2—C1—C6—N1	−179.8 (2)
C1—S1—C7—N2	−176.53 (19)	C2—C1—C6—C5	0.4 (3)
C7—N1—C6—C1	−0.6 (3)	C1—C2—C3—C4	1.4 (4)
C7—N1—C6—C5	179.2 (2)	C2—C3—C4—C5	−0.6 (4)
C6—N1—C7—S1	0.9 (2)	C3—C4—C5—C6	−0.3 (4)
C6—N1—C7—N2	176.3 (2)	C4—C5—C6—N1	−179.4 (2)
S1—C1—C2—C3	179.0 (2)	C4—C5—C6—C1	0.4 (3)
C6—C1—C2—C3	−1.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···N1i	0.83 (2)	2.14 (2)	2.964 (3)	172 (2)
N2—H2A···N2ii	0.80 (2)	2.46 (2)	3.217 (3)	157 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯N1i	0.83 (2)	2.14 (2)	2.964 (3)	172 (2)
N2—H2A⋯N2ii	0.80 (2)	2.46 (2)	3.217 (3)	157 (2)

Symmetry codes: (i) ; (ii) .