2-Amino-6-nitro-1,3-benzothia-zol-3-ium hydrogen sulfate.

In the title molecular salt, C(7)H(6)N(3)O(2)S(+)·HSO(4) (-), the 2-amino-6-nitro-1,3-benzothia-zole ring system is essentially planar [mean deviation = 0.0605 (4) Å]. In the crystal, N-H⋯O and O-H⋯O hydrogen-bonding inter-actions result in a layer motif.

Related literature

For related compounds, see Glidewell et al. (2001 ▶); Lynch (2002 ▶); Lynch & Duckhouse (2001 ▶); You et al. (2009 ▶).

Experimental

Crystal data

C7H6N3O2S+·HSO4 −

M = 293.28

Monoclinic,

a = 7.849 (6) Å

b = 16.219 (12) Å

c = 9.191 (7) Å

β = 108.584 (10)°

V = 1109.0 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.51 mm−1

T = 291 K

0.16 × 0.14 × 0.12 mm

Data collection

Bruker 1K CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.923, T max = 0.942

5436 measured reflections

1958 independent reflections

1586 reflections with I > 2σ(I)

R int = 0.097

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.159

S = 0.98

1958 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.60 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811027620/ff2020sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811027620/ff2020Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811027620/ff2020Isup3.cml

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

C7H6N3O2S+·HSO4−	F(000) = 600
Mr = 293.28	Dx = 1.757 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2618 reflections
a = 7.849 (6) Å	θ = 2.3–28.0°
b = 16.219 (12) Å	µ = 0.51 mm−1
c = 9.191 (7) Å	T = 291 K
β = 108.584 (10)°	Block, colourless
V = 1109.0 (14) Å3	0.16 × 0.14 × 0.12 mm
Z = 4

Bruker 1K CCD area-detector diffractometer	1958 independent reflections
Radiation source: fine-focus sealed tube	1586 reflections with I > 2σ(I)
graphite	Rint = 0.097
φ and ω scans	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→6
Tmin = 0.923, Tmax = 0.942	k = −19→18
5436 measured reflections	l = −8→10

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.1126P)2] where P = (Fo2 + 2Fc2)/3
1958 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.60 e Å−3

Experimental. The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses.

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
C1	0.7190 (4)	0.12918 (17)	0.4541 (3)	0.0400 (7)
C2	0.7416 (4)	−0.00938 (16)	0.5027 (3)	0.0379 (7)
C3	0.7086 (5)	−0.09352 (18)	0.4792 (4)	0.0483 (8)
H3	0.6294	−0.1131	0.3874	0.058*
C4	0.7959 (5)	−0.14661 (19)	0.5950 (4)	0.0501 (8)
H4	0.7790	−0.2032	0.5815	0.060*
C5	0.9089 (4)	−0.11571 (17)	0.7315 (4)	0.0427 (7)
C6	0.9441 (4)	−0.03251 (17)	0.7588 (3)	0.0427 (7)
H6	1.0207	−0.0132	0.8520	0.051*
C7	0.8588 (4)	0.02045 (17)	0.6393 (3)	0.0387 (7)
N1	0.6668 (3)	0.05352 (15)	0.4010 (3)	0.0412 (6)
H1A	0.5927	0.0447	0.3107	0.049*
N2	0.6630 (4)	0.19655 (15)	0.3774 (3)	0.0524 (8)
H2A	0.5874	0.1941	0.2861	0.063*
H2B	0.7014	0.2436	0.4178	0.063*
N3	0.9911 (4)	−0.17264 (18)	0.8562 (3)	0.0538 (7)
O1	1.0531 (3)	−0.14566 (16)	0.9864 (3)	0.0651 (7)
O2	0.9914 (5)	−0.24573 (18)	0.8252 (3)	0.0885 (10)
O3	0.4172 (3)	0.88694 (13)	1.0011 (3)	0.0602 (7)
H3A	0.3934	0.9305	1.0357	0.090*
O4	0.6040 (3)	0.96348 (13)	0.8861 (2)	0.0479 (6)
O5	0.7360 (3)	0.90117 (14)	1.1335 (3)	0.0607 (7)
O6	0.6226 (3)	0.81597 (13)	0.9086 (3)	0.0549 (7)
S1	0.87176 (11)	0.12757 (5)	0.63686 (9)	0.0506 (3)
S2	0.60859 (9)	0.89227 (4)	0.98544 (8)	0.0401 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0477 (16)	0.0359 (15)	0.0280 (16)	−0.0021 (12)	0.0003 (13)	0.0006 (12)
C2	0.0509 (16)	0.0330 (14)	0.0274 (15)	−0.0023 (12)	0.0092 (13)	0.0000 (11)
C3	0.067 (2)	0.0398 (16)	0.0321 (16)	−0.0075 (15)	0.0077 (14)	−0.0101 (13)
C4	0.072 (2)	0.0347 (15)	0.0430 (19)	0.0010 (15)	0.0172 (16)	0.0014 (14)
C5	0.0461 (16)	0.0434 (17)	0.0365 (17)	0.0047 (13)	0.0103 (14)	0.0073 (13)
C6	0.0451 (16)	0.0452 (16)	0.0315 (16)	−0.0033 (13)	0.0034 (13)	0.0035 (13)
C7	0.0449 (15)	0.0351 (15)	0.0312 (15)	−0.0024 (12)	0.0053 (12)	−0.0006 (11)
N1	0.0530 (14)	0.0383 (13)	0.0239 (12)	−0.0053 (11)	0.0005 (10)	−0.0023 (10)
N2	0.0697 (18)	0.0341 (13)	0.0363 (15)	−0.0036 (12)	−0.0073 (13)	−0.0003 (11)
N3	0.0579 (16)	0.0541 (17)	0.0479 (19)	0.0046 (13)	0.0149 (14)	0.0168 (14)
O1	0.0650 (15)	0.0766 (18)	0.0433 (16)	−0.0019 (13)	0.0025 (12)	0.0191 (13)
O2	0.131 (3)	0.0496 (15)	0.073 (2)	0.0216 (16)	0.0161 (17)	0.0176 (14)
O3	0.0525 (14)	0.0479 (13)	0.081 (2)	−0.0029 (10)	0.0230 (14)	−0.0050 (12)
O4	0.0656 (14)	0.0382 (11)	0.0354 (12)	0.0087 (10)	0.0099 (10)	0.0037 (9)
O5	0.0633 (15)	0.0678 (16)	0.0346 (13)	−0.0024 (11)	−0.0077 (11)	−0.0017 (11)
O6	0.0696 (15)	0.0379 (12)	0.0450 (14)	0.0118 (10)	0.0013 (11)	−0.0044 (10)
S1	0.0641 (6)	0.0364 (5)	0.0329 (5)	−0.0078 (3)	−0.0104 (4)	−0.0014 (3)
S2	0.0452 (5)	0.0362 (5)	0.0297 (5)	0.0029 (3)	−0.0010 (4)	−0.0023 (3)

C1—N2	1.299 (4)	C6—H6	0.9300
C1—N1	1.336 (3)	C7—S1	1.741 (3)
C1—S1	1.725 (3)	N1—H1A	0.8600
C2—N1	1.382 (3)	N2—H2A	0.8600
C2—C7	1.386 (4)	N2—H2B	0.8600
C2—C3	1.393 (4)	N3—O1	1.220 (4)
C3—C4	1.370 (4)	N3—O2	1.220 (4)
C3—H3	0.9300	O3—S2	1.557 (3)
C4—C5	1.380 (5)	O3—H3A	0.8200
C4—H4	0.9300	O4—S2	1.466 (2)
C5—C6	1.384 (4)	O5—S2	1.416 (2)
C5—N3	1.453 (4)	O6—S2	1.446 (2)
C6—C7	1.387 (4)
N2—C1—N1	124.2 (3)	C2—C7—S1	111.2 (2)
N2—C1—S1	123.5 (2)	C6—C7—S1	127.8 (2)
N1—C1—S1	112.3 (2)	C1—N1—C2	114.6 (2)
N1—C2—C7	111.8 (2)	C1—N1—H1A	122.7
N1—C2—C3	126.9 (3)	C2—N1—H1A	122.7
C7—C2—C3	121.3 (3)	C1—N2—H2A	120.0
C4—C3—C2	118.2 (3)	C1—N2—H2B	120.0
C4—C3—H3	120.9	H2A—N2—H2B	120.0
C2—C3—H3	120.9	O1—N3—O2	123.3 (3)
C3—C4—C5	119.7 (3)	O1—N3—C5	118.9 (3)
C3—C4—H4	120.2	O2—N3—C5	117.8 (3)
C5—C4—H4	120.2	S2—O3—H3A	109.5
C4—C5—C6	123.5 (3)	C1—S1—C7	90.14 (13)
C4—C5—N3	118.8 (3)	O5—S2—O6	114.58 (14)
C6—C5—N3	117.6 (3)	O5—S2—O4	112.84 (14)
C5—C6—C7	116.2 (3)	O6—S2—O4	111.16 (15)
C5—C6—H6	121.9	O5—S2—O3	108.89 (16)
C7—C6—H6	121.9	O6—S2—O3	102.90 (14)
C2—C7—C6	121.0 (3)	O4—S2—O3	105.57 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4i	0.86	1.97	2.825 (4)	171
N2—H2A···O6i	0.86	2.02	2.867 (4)	170
N2—H2B···O6ii	0.86	2.10	2.888 (4)	151
O3—H3A···O4iii	0.82	1.86	2.664 (4)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O4i	0.86	1.97	2.825 (4)	171
N2—H2A⋯O6i	0.86	2.02	2.867 (4)	170
N2—H2B⋯O6ii	0.86	2.10	2.888 (4)	151
O3—H3A⋯O4iii	0.82	1.86	2.664 (4)	166

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