2-Hydrazinyl-4-methyl-1,3-benzothia-zole.

The title compound, C(8)H(9)N(3)S, is almost planar (r.m.s. deviation = 0.019 Å) apart from the terminal -NH(2) grouping [deviation of the N atom = 0.286 (2) Å]. In the crystal, mol-ecules are linked by N-H⋯N hydrogen bonds, generating (001) sheets.

Related literature

For related structures and their biactivity, see Sun & Cui (2008 ▶); Liu & Liu (2011 ▶); Liuet al. (2011a ▶,b ▶). For the synthesis, see: Patel et al. (2010 ▶).

Experimental

Crystal data

C8H9N3S

M = 179.24

Monoclinic,

a = 3.893 (2) Å

b = 7.312 (4) Å

c = 14.137 (8) Å

β = 93.416 (13)°

V = 401.7 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.34 mm−1

T = 113 K

0.28 × 0.18 × 0.10 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.910, T max = 0.967

4186 measured reflections

1864 independent reflections

1614 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.057

S = 1.02

1864 reflections

122 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack (1983 ▶), 836 Friedel pairs

Flack parameter: −0.09 (6)

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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) global, I. DOI: 10.1107/S1600536811020149/hb5894sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020149/hb5894Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811020149/hb5894Isup3.cml

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

C8H9N3S	F(000) = 188
Mr = 179.24	Dx = 1.482 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 3.893 (2) Å	Cell parameters from 1356 reflections
b = 7.312 (4) Å	θ = 2.9–27.9°
c = 14.137 (8) Å	µ = 0.34 mm−1
β = 93.416 (13)°	T = 113 K
V = 401.7 (4) Å3	Prism, colorless
Z = 2	0.28 × 0.18 × 0.10 mm

Rigaku Saturn CCD area-detector diffractometer	1864 independent reflections
Radiation source: rotating anode	1614 reflections with I > 2σ(I)
multilayer	Rint = 0.043
Detector resolution: 14.63 pixels mm-1	θmax = 27.9°, θmin = 1.4°
ω and φ scans	h = −5→5
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −9→9
Tmin = 0.910, Tmax = 0.967	l = −18→18
4186 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)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.057	w = 1/[σ2(Fo2) + (0.006P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
1864 reflections	Δρmax = 0.28 e Å−3
122 parameters	Δρmin = −0.20 e Å−3
5 restraints	Absolute structure: Flack (1983), 836 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.09 (6)

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	0.74281 (13)	0.41481 (6)	0.33097 (3)	0.01462 (12)
C5	0.2809 (5)	0.8047 (3)	0.18122 (14)	0.0144 (5)
N3	0.9465 (5)	0.4807 (2)	0.52579 (12)	0.0163 (4)
C2	0.5274 (5)	0.4513 (3)	0.13713 (13)	0.0163 (5)
H2A	0.6107	0.3333	0.1221	0.020*
N1	0.4899 (4)	0.7443 (2)	0.34709 (11)	0.0136 (4)
C4	0.2524 (5)	0.7352 (3)	0.08962 (14)	0.0158 (5)
H4	0.1480	0.8083	0.0403	0.019*
C6	0.4388 (5)	0.6942 (3)	0.25178 (13)	0.0127 (4)
C7	0.6412 (5)	0.6127 (3)	0.39382 (13)	0.0130 (4)
N2	0.7110 (4)	0.6159 (2)	0.49033 (12)	0.0150 (4)
C3	0.3711 (5)	0.5633 (3)	0.06809 (13)	0.0185 (5)
H3	0.3451	0.5208	0.0046	0.022*
C1	0.5572 (5)	0.5186 (3)	0.22906 (13)	0.0124 (4)
C8	0.1482 (5)	0.9932 (3)	0.20484 (14)	0.0182 (5)
H8A	0.3296	1.0618	0.2404	0.027*
H8B	−0.0518	0.9812	0.2433	0.027*
H8C	0.0810	1.0585	0.1461	0.027*
H2	0.761 (6)	0.7236 (19)	0.5172 (16)	0.060 (10)*
H3A	0.861 (4)	0.423 (3)	0.5774 (10)	0.043 (7)*
H3B	1.153 (3)	0.531 (3)	0.5428 (12)	0.038 (8)*

	U11	U22	U33	U12	U13	U23
S1	0.0167 (3)	0.0120 (2)	0.0151 (2)	0.0012 (3)	0.00115 (18)	0.0003 (2)
C5	0.0078 (11)	0.0166 (11)	0.0191 (11)	−0.0007 (10)	0.0026 (9)	0.0030 (9)
N3	0.0141 (11)	0.0180 (10)	0.0163 (9)	0.0006 (8)	−0.0015 (7)	0.0049 (8)
C2	0.0142 (11)	0.0169 (14)	0.0180 (10)	−0.0005 (9)	0.0029 (8)	−0.0029 (9)
N1	0.0139 (10)	0.0126 (9)	0.0142 (9)	0.0000 (7)	0.0007 (7)	0.0017 (7)
C4	0.0124 (12)	0.0188 (11)	0.0163 (11)	−0.0008 (9)	0.0004 (8)	0.0044 (9)
C6	0.0091 (10)	0.0132 (10)	0.0160 (10)	−0.0037 (9)	0.0032 (8)	0.0004 (9)
C7	0.0125 (11)	0.0137 (10)	0.0133 (10)	−0.0043 (9)	0.0033 (9)	−0.0010 (9)
N2	0.0186 (11)	0.0117 (9)	0.0145 (9)	0.0011 (8)	−0.0009 (7)	0.0004 (8)
C3	0.0189 (13)	0.0231 (12)	0.0133 (10)	−0.0065 (9)	0.0009 (9)	−0.0015 (10)
C1	0.0113 (11)	0.0129 (11)	0.0129 (10)	0.0004 (9)	0.0005 (8)	0.0027 (8)
C8	0.0167 (13)	0.0162 (10)	0.0215 (11)	0.0010 (10)	−0.0008 (9)	0.0034 (9)

S1—C1	1.746 (2)	N1—C7	1.289 (2)
S1—C7	1.756 (2)	N1—C6	1.399 (2)
C5—C4	1.389 (3)	C4—C3	1.379 (3)
C5—C6	1.397 (3)	C4—H4	0.9500
C5—C8	1.516 (3)	C6—C1	1.407 (2)
N3—N2	1.420 (2)	C7—N2	1.375 (3)
N3—H3A	0.923 (9)	N2—H2	0.891 (9)
N3—H3B	0.903 (9)	C3—H3	0.9500
C2—C3	1.387 (3)	C8—H8A	0.9800
C2—C1	1.388 (2)	C8—H8B	0.9800
C2—H2A	0.9500	C8—H8C	0.9800
C1—S1—C7	87.97 (10)	N1—C7—S1	117.74 (15)
C4—C5—C6	117.47 (18)	N2—C7—S1	118.61 (15)
C4—C5—C8	121.90 (18)	C7—N2—N3	115.08 (15)
C6—C5—C8	120.64 (17)	C7—N2—H2	117.6 (16)
N2—N3—H3A	110.0 (13)	N3—N2—H2	110.2 (17)
N2—N3—H3B	110.7 (14)	C4—C3—C2	121.44 (19)
H3A—N3—H3B	109.6 (12)	C4—C3—H3	119.3
C3—C2—C1	117.26 (17)	C2—C3—H3	119.3
C3—C2—H2A	121.4	C2—C1—C6	121.80 (18)
C1—C2—H2A	121.4	C2—C1—S1	128.72 (15)
C7—N1—C6	109.43 (16)	C6—C1—S1	109.47 (14)
C3—C4—C5	121.98 (19)	C5—C8—H8A	109.5
C3—C4—H4	119.0	C5—C8—H8B	109.5
C5—C4—H4	119.0	H8A—C8—H8B	109.5
C5—C6—N1	124.57 (18)	C5—C8—H8C	109.5
C5—C6—C1	120.04 (17)	H8A—C8—H8C	109.5
N1—C6—C1	115.39 (17)	H8B—C8—H8C	109.5
N1—C7—N2	123.57 (18)
C6—C5—C4—C3	0.6 (3)	N1—C7—N2—N3	−165.94 (18)
C8—C5—C4—C3	−179.61 (17)	S1—C7—N2—N3	17.4 (2)
C4—C5—C6—N1	179.46 (18)	C5—C4—C3—C2	−0.4 (3)
C8—C5—C6—N1	−0.3 (3)	C1—C2—C3—C4	0.5 (3)
C4—C5—C6—C1	−0.9 (3)	C3—C2—C1—C6	−0.9 (3)
C8—C5—C6—C1	179.27 (16)	C3—C2—C1—S1	−179.19 (14)
C7—N1—C6—C5	179.87 (19)	C5—C6—C1—C2	1.1 (3)
C7—N1—C6—C1	0.3 (2)	N1—C6—C1—C2	−179.26 (17)
C6—N1—C7—N2	−176.41 (18)	C5—C6—C1—S1	179.73 (15)
C6—N1—C7—S1	0.3 (2)	N1—C6—C1—S1	−0.6 (2)
C1—S1—C7—N1	−0.54 (17)	C7—S1—C1—C2	179.11 (18)
C1—S1—C7—N2	176.31 (16)	C7—S1—C1—C6	0.61 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N3i	0.89 (1)	2.30 (2)	2.996 (3)	135 (2)
N3—H3A···N1ii	0.92 (1)	2.21 (1)	3.077 (3)	156.(2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N3i	0.89 (1)	2.30 (2)	2.996 (3)	135 (2)
N3—H3A⋯N1ii	0.92 (1)	2.21 (1)	3.077 (3)	156 (2)

Symmetry codes: (i) ; (ii) .