1H-Pyrazolo[4,3-g]benzothia-zol-7-amine.

The mol-ecule of the title compound, C(8)H(6)N(4)S, is almost planar [maximum deviation from the mean plane = 0.020 (1) Å for the S atom]. In the crystal, a supra-molecular three-dimensional arrangement arises from N-H⋯N hydrogen bonds and weak aromatic stacking interactions along the a axis [centroid-centroid separation = 3.582 (2) Å].

Related literature

For background on DNA inter­calation agents, see: Cagnoli et al. (1968 ▶); Martínez & Chacón-García (2005 ▶); Chakrabarty et al. (2008 ▶). For further synthetic details, see: Salazar & Dorta (2004 ▶).

Experimental

Crystal data

C8H6N4S

M = 190.23

Monoclinic,

a = 4.499 (2) Å

b = 14.979 (8) Å

c = 12.112 (7) Å

β = 92.442 (19)°

V = 815.6 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.35 mm−1

T = 293 K

0.50 × 0.48 × 0.28 mm

Data collection

Rigaku AFC7S Mercury diffractometer

Absorption correction: multi-scan (Jacobson, 1998 ▶) T min = 0.837, T max = 0.904

8415 measured reflections

1564 independent reflections

1356 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.117

S = 1.12

1564 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.39 e Å−3

Data collection: CrystalClear (Rigaku, 2002 ▶); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXTL-NT (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL-NT; molecular graphics: SHELXTL-NT and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL-NT and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I. DOI: 10.1107/S1600536809012550/hb2931sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809012550/hb2931Isup2.hkl

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

C8H6N4S	F(000) = 392
Mr = 190.23	Dx = 1.549 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybc	Cell parameters from 5546 reflections
a = 4.499 (2) Å	θ = 1.4–27.8°
b = 14.979 (8) Å	µ = 0.35 mm−1
c = 12.112 (7) Å	T = 293 K
β = 92.442 (19)°	Block, light brown
V = 815.6 (7) Å3	0.50 × 0.48 × 0.28 mm
Z = 4

Rigaku AFC7S Mercury diffractometer	1564 independent reflections
Radiation source: Normal-focus sealed tube	1356 reflections with I > 2σ(I)
graphite	Rint = 0.027
ω scans	θmax = 27.8°, θmin = 2.2°
Absorption correction: multi-scan (Jacobson, 1998)	h = −5→5
Tmin = 0.837, Tmax = 0.904	k = −17→17
8415 measured reflections	l = −10→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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0537P)2 + 0.4259P] where P = (Fo2 + 2Fc2)/3
1564 reflections	(Δ/σ)max = 0.001
118 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.38 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	1.01959 (12)	0.29819 (4)	0.80928 (4)	0.0375 (2)
N1	0.4558 (5)	0.03847 (13)	0.69844 (15)	0.0469 (5)
N2	0.6362 (4)	0.11194 (12)	0.70868 (14)	0.0399 (5)
H2	0.7275	0.1305	0.6432	0.048*
N3	0.8801 (4)	0.31237 (12)	1.01512 (15)	0.0374 (4)
N4	1.2153 (5)	0.42105 (13)	0.95801 (16)	0.0467 (5)
H6	1.3202	0.4479	0.8999	0.056*
H5	1.2408	0.4424	1.0345	0.056*
C1	0.3414 (6)	0.02732 (16)	0.79596 (19)	0.0447 (6)
H1	0.2103	−0.0183	0.8125	0.054*
C2	0.4424 (5)	0.09335 (14)	0.87253 (17)	0.0364 (5)
C3	0.3893 (5)	0.11384 (15)	0.98363 (18)	0.0425 (5)
H3	0.2600	0.0790	1.0233	0.051*
C4	0.5305 (5)	0.18567 (15)	1.03243 (18)	0.0408 (5)
H4	0.4976	0.1996	1.1057	0.049*
C5	0.7267 (5)	0.23892 (14)	0.97160 (16)	0.0352 (5)
C6	1.0420 (5)	0.34903 (14)	0.94037 (17)	0.0354 (5)
C7	0.7767 (5)	0.22046 (13)	0.86132 (16)	0.0319 (5)
C8	0.6336 (5)	0.14676 (14)	0.81177 (16)	0.0333 (5)

	U11	U22	U33	U12	U13	U23
S1	0.0429 (4)	0.0374 (4)	0.0325 (4)	−0.0007 (2)	0.0051 (2)	0.00195 (19)
N1	0.0621 (14)	0.0372 (11)	0.0414 (11)	−0.0055 (9)	0.0022 (9)	−0.0022 (8)
N2	0.0526 (12)	0.0365 (10)	0.0308 (10)	−0.0003 (9)	0.0058 (8)	−0.0021 (7)
N3	0.0424 (11)	0.0372 (10)	0.0326 (10)	0.0027 (8)	0.0028 (8)	−0.0032 (7)
N4	0.0574 (13)	0.0421 (11)	0.0405 (11)	−0.0088 (9)	0.0014 (9)	0.0000 (8)
C1	0.0550 (15)	0.0365 (12)	0.0426 (13)	−0.0047 (10)	0.0028 (10)	0.0023 (9)
C2	0.0414 (13)	0.0312 (11)	0.0367 (11)	0.0028 (9)	0.0031 (9)	0.0043 (8)
C3	0.0489 (14)	0.0417 (13)	0.0375 (12)	−0.0020 (10)	0.0084 (10)	0.0051 (9)
C4	0.0503 (14)	0.0439 (13)	0.0290 (11)	0.0011 (10)	0.0091 (10)	0.0018 (8)
C5	0.0385 (12)	0.0340 (11)	0.0331 (11)	0.0060 (9)	0.0029 (8)	0.0005 (8)
C6	0.0363 (12)	0.0334 (11)	0.0364 (11)	0.0055 (9)	−0.0002 (8)	0.0019 (8)
C7	0.0346 (12)	0.0323 (11)	0.0289 (10)	0.0054 (9)	0.0038 (8)	0.0016 (8)
C8	0.0384 (12)	0.0312 (11)	0.0303 (10)	0.0083 (9)	0.0011 (8)	0.0007 (8)

S1—C7	1.734 (2)	C1—C2	1.418 (3)
S1—C6	1.760 (2)	C1—H1	0.9300
N1—C1	1.319 (3)	C2—C8	1.405 (3)
N1—N2	1.370 (3)	C2—C3	1.411 (3)
N2—C8	1.354 (3)	C3—C4	1.371 (3)
N2—H2	0.9500	C3—H3	0.9300
N3—C6	1.307 (3)	C4—C5	1.419 (3)
N3—C5	1.391 (3)	C4—H4	0.9300
N4—C6	1.343 (3)	C5—C7	1.392 (3)
N4—H6	0.9529	C7—C8	1.400 (3)
N4—H5	0.9822
C7—S1—C6	88.59 (10)	C2—C3—H3	120.4
C1—N1—N2	105.85 (18)	C3—C4—C5	120.3 (2)
C8—N2—N1	111.39 (18)	C3—C4—H4	119.9
C8—N2—H2	132.7	C5—C4—H4	119.9
N1—N2—H2	115.8	N3—C5—C7	115.03 (19)
C6—N3—C5	110.62 (18)	N3—C5—C4	123.89 (19)
C6—N4—H6	121.6	C7—C5—C4	121.1 (2)
C6—N4—H5	117.1	N3—C6—N4	124.3 (2)
H6—N4—H5	121.2	N3—C6—S1	115.53 (17)
N1—C1—C2	111.8 (2)	N4—C6—S1	120.12 (16)
N1—C1—H1	124.1	C5—C7—C8	118.54 (19)
C2—C1—H1	124.1	C5—C7—S1	110.22 (16)
C8—C2—C3	120.5 (2)	C8—C7—S1	131.23 (16)
C8—C2—C1	103.94 (19)	N2—C8—C7	132.6 (2)
C3—C2—C1	135.5 (2)	N2—C8—C2	107.05 (19)
C4—C3—C2	119.2 (2)	C7—C8—C2	120.32 (19)
C4—C3—H3	120.4

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N3i	0.95	1.92	2.864 (3)	170
N4—H5···N1ii	0.98	2.19	3.123 (3)	158
N4—H6···N1iii	0.95	2.09	3.019 (3)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N3i	0.95	1.92	2.864 (3)	170
N4—H5⋯N1ii	0.98	2.19	3.123 (3)	158
N4—H6⋯N1iii	0.95	2.09	3.019 (3)	164

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