6-Meth-oxy-1,3-benzothia-zol-2-amine.

The title compound, C(8)H(8)N(2)OS, is almost planar, the C-C-O-C torsion angle associated with the meth-oxy group being 0.72 (1)°. Inter-molecular amine N-H⋯N hydrogen-bonding inter-actions form inversion dimers [graph set R(2) (2)(8)] which are extended into chains along the b axis through amine N-H⋯O hydrogen bonds.

Related literature

For information on various important biological activities of amino­benzothia­zoles, see: Hutchinson et al. (2002 ▶); Benavides et al. (1985 ▶); La’cova et al. (1991 ▶). For their pharmaceutical applications, see: Suter & Zutter (1967 ▶); Sawhney et al. (1978 ▶); Bensimon et al. (1994 ▶); Foscolos et al. (1977 ▶); Shirke et al. (1990 ▶); Paget et al. (1969 ▶); Domino et al. (1952 ▶). For anti­microbial and pesticidal activities, see: Pattan et al. (2002 ▶); Kaufmann (1935 ▶). For related structures see: Saeed et al. (2007 ▶); Sun et al. (2011 ▶). For graph-set analysis, see: Etter et al. (1990 ▶).

Experimental

Crystal data

C8H8N2OS

M = 180.23

Orthorhombic,

a = 15.060 (2) Å

b = 6.6997 (11) Å

c = 16.649 (3) Å

V = 1679.8 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.33 mm−1

T = 130 K

0.47 × 0.23 × 0.14 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.859, T max = 0.955

14745 measured reflections

2010 independent reflections

1771 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.094

S = 1.06

2010 reflections

110 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.20 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and local programs.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812028152/zs2217sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028152/zs2217Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812028152/zs2217Isup3.mol

Supplementary material file. DOI: 10.1107/S1600536812028152/zs2217Isup4.cml

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

C8H8N2OS	Dx = 1.425 Mg m−3
Mr = 180.23	Melting point = 418–420 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3739 reflections
a = 15.060 (2) Å	θ = 2.5–28.3°
b = 6.6997 (11) Å	µ = 0.33 mm−1
c = 16.649 (3) Å	T = 130 K
V = 1679.8 (5) Å3	Prism, colourless
Z = 8	0.47 × 0.23 × 0.14 mm
F(000) = 752

Bruker SMART APEX CCD diffractometer	2010 independent reflections
Radiation source: sealed tube	1771 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scans	θmax = 27.9°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −19→19
Tmin = 0.859, Tmax = 0.955	k = −8→8
14745 measured reflections	l = −21→20

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)] = 0.033	Hydrogen site location: difference Fourier map
wR(F2) = 0.094	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0541P)2 + 0.5583P] where P = (Fo2 + 2Fc2)/3
2010 reflections	(Δ/σ)max = 0.001
110 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.20 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	0.67080 (2)	0.21698 (5)	0.37026 (2)	0.02447 (13)
O1	0.68079 (6)	0.55013 (14)	0.09070 (6)	0.0234 (2)
N1	0.56180 (7)	0.50795 (17)	0.40573 (6)	0.0217 (2)
N2	0.58824 (8)	0.28778 (19)	0.51177 (7)	0.0292 (3)
H2A	0.5525	0.3536	0.5442	0.035*
H2B	0.6160	0.1805	0.5290	0.035*
C1	0.60027 (9)	0.3510 (2)	0.43608 (8)	0.0220 (3)
C2	0.58749 (8)	0.53507 (19)	0.32593 (8)	0.0191 (3)
C3	0.56017 (9)	0.6894 (2)	0.27627 (8)	0.0225 (3)
H3A	0.5211	0.7892	0.2962	0.027*
C4	0.58993 (9)	0.6982 (2)	0.19719 (8)	0.0220 (3)
H4A	0.5710	0.8036	0.1630	0.026*
C5	0.64762 (8)	0.55186 (19)	0.16817 (8)	0.0193 (3)
C6	0.67681 (8)	0.3964 (2)	0.21681 (8)	0.0209 (3)
H6A	0.7162	0.2973	0.1968	0.025*
C7	0.64648 (8)	0.39071 (19)	0.29540 (8)	0.0193 (3)
C8	0.65274 (10)	0.7074 (2)	0.03804 (9)	0.0281 (3)
H8A	0.5878	0.7068	0.0340	0.042*
H8B	0.6786	0.6867	−0.0153	0.042*
H8C	0.6726	0.8360	0.0595	0.042*

	U11	U22	U33	U12	U13	U23
S1	0.0272 (2)	0.0253 (2)	0.0208 (2)	0.00985 (13)	0.00107 (13)	0.00191 (12)
O1	0.0249 (5)	0.0256 (5)	0.0195 (5)	0.0008 (4)	0.0041 (4)	0.0015 (4)
N1	0.0242 (5)	0.0232 (5)	0.0177 (5)	0.0041 (4)	−0.0009 (4)	−0.0017 (4)
N2	0.0358 (7)	0.0314 (7)	0.0203 (6)	0.0133 (5)	0.0027 (5)	0.0039 (5)
C1	0.0220 (6)	0.0253 (7)	0.0187 (6)	0.0030 (5)	−0.0011 (5)	−0.0028 (5)
C2	0.0178 (6)	0.0215 (6)	0.0180 (6)	0.0010 (5)	−0.0013 (5)	−0.0027 (5)
C3	0.0230 (6)	0.0224 (6)	0.0223 (6)	0.0058 (5)	0.0005 (5)	−0.0014 (5)
C4	0.0220 (6)	0.0220 (6)	0.0220 (7)	0.0020 (5)	−0.0016 (5)	0.0017 (5)
C5	0.0177 (6)	0.0222 (6)	0.0181 (6)	−0.0034 (5)	0.0012 (5)	−0.0020 (5)
C6	0.0182 (6)	0.0217 (6)	0.0229 (7)	0.0026 (5)	0.0010 (5)	−0.0027 (5)
C7	0.0182 (6)	0.0196 (6)	0.0202 (6)	0.0018 (5)	−0.0027 (5)	−0.0012 (5)
C8	0.0339 (8)	0.0290 (8)	0.0213 (7)	−0.0006 (6)	0.0037 (6)	0.0052 (6)

S1—C7	1.7443 (13)	C3—C4	1.3920 (19)
S1—C1	1.7705 (14)	C3—H3A	0.9500
O1—C5	1.3832 (16)	C4—C5	1.3962 (18)
O1—C8	1.4342 (17)	C4—H4A	0.9500
N1—C1	1.3028 (18)	C5—C6	1.3908 (18)
N1—C2	1.3956 (17)	C6—C7	1.3864 (18)
N2—C1	1.3417 (18)	C6—H6A	0.9500
N2—H2A	0.8800	C8—H8A	0.9800
N2—H2B	0.8800	C8—H8B	0.9800
C2—C3	1.3864 (18)	C8—H8C	0.9800
C2—C7	1.4083 (18)
C7—S1—C1	88.73 (6)	C5—C4—H4A	120.1
C5—O1—C8	117.23 (10)	O1—C5—C6	114.99 (11)
C1—N1—C2	110.55 (11)	O1—C5—C4	123.59 (12)
C1—N2—H2A	120.0	C6—C5—C4	121.42 (12)
C1—N2—H2B	120.0	C7—C6—C5	117.76 (12)
H2A—N2—H2B	120.0	C7—C6—H6A	121.1
N1—C1—N2	123.98 (13)	C5—C6—H6A	121.1
N1—C1—S1	115.86 (10)	C6—C7—C2	121.99 (12)
N2—C1—S1	120.15 (11)	C6—C7—S1	128.57 (10)
C3—C2—N1	125.63 (12)	C2—C7—S1	109.44 (10)
C3—C2—C7	118.96 (12)	O1—C8—H8A	109.5
N1—C2—C7	115.41 (11)	O1—C8—H8B	109.5
C2—C3—C4	120.01 (12)	H8A—C8—H8B	109.5
C2—C3—H3A	120.0	O1—C8—H8C	109.5
C4—C3—H3A	120.0	H8A—C8—H8C	109.5
C3—C4—C5	119.86 (12)	H8B—C8—H8C	109.5
C3—C4—H4A	120.1
C2—N1—C1—N2	179.99 (13)	C3—C4—C5—C6	−0.3 (2)
C2—N1—C1—S1	−0.87 (15)	O1—C5—C6—C7	179.48 (11)
C7—S1—C1—N1	0.50 (11)	C4—C5—C6—C7	0.19 (19)
C7—S1—C1—N2	179.67 (12)	C5—C6—C7—C2	0.6 (2)
C1—N1—C2—C3	−178.88 (13)	C5—C6—C7—S1	−179.95 (10)
C1—N1—C2—C7	0.90 (17)	C3—C2—C7—C6	−1.2 (2)
N1—C2—C3—C4	−179.23 (12)	N1—C2—C7—C6	179.05 (12)
C7—C2—C3—C4	1.0 (2)	C3—C2—C7—S1	179.27 (10)
C2—C3—C4—C5	−0.3 (2)	N1—C2—C7—S1	−0.53 (15)
C8—O1—C5—C6	180.00 (11)	C1—S1—C7—C6	−179.51 (13)
C8—O1—C5—C4	−0.72 (18)	C1—S1—C7—C2	0.04 (10)
C3—C4—C5—O1	−179.55 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1i	0.88	2.13	2.9774 (16)	163
N2—H2B···O1ii	0.88	2.10	2.9655 (16)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N1i	0.88	2.13	2.9774 (16)	163
N2—H2B⋯O1ii	0.88	2.10	2.9655 (16)	170

Symmetry codes: (i) ; (ii) .