4-Sulfamoylanilinium nitrate.

In the crystal structure of the title compound, C(6)H(9)N(2)O(2)S(+)·NO(3) (-), the cations and anions are connected by N-H⋯O hydrogen bonds into a three-dimensional network.

Related literature

For the biological importance of the title compound, see: Kent (2000 ▶). For related structures, see: Alléaume & Decap (1965a ▶,b ▶); Buttle et al. (1936 ▶); Chatterjee et al. (1981 ▶); Gelbrich et al. (2007 ▶, 2008 ▶); Gelmboldt et al. (2004 ▶); Hughes et al. (1999 ▶); O’Connell & Maslen (1967 ▶); O’Connor & Maslen (1965 ▶); Smith et al. (2001 ▶); Zaouali Zgolli et al. (2010 ▶). For the polymorphism of sulfanilamide, see: Burger (1973 ▶). For hydrogen-bond motifs, see: Etter et al. (1990 ▶).

Experimental

Crystal data

C6H9N2O2S+·NO3 −

M = 235.22

Monoclinic,

a = 14.1489 (19) Å

b = 8.1786 (11) Å

c = 8.6931 (12) Å

β = 107.129 (2)°

V = 961.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.34 mm−1

T = 293 K

0.24 × 0.22 × 0.19 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

4345 measured reflections

1694 independent reflections

1689 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.061

S = 1.15

1694 reflections

157 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.25 e Å−3

Absolute structure: Flack (1983 ▶), 840 Friedel pairs

Flack parameter: 0.06 (5)

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL/PC (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL/PC; molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL/PC.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811038827/bt5645sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811038827/bt5645Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811038827/bt5645Isup3.cml

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

C6H9N2O2S+·NO3−	F(000) = 488
Mr = 235.22	Dx = 1.625 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 2432 reflections
a = 14.1489 (19) Å	θ = 2.3–24.3°
b = 8.1786 (11) Å	µ = 0.34 mm−1
c = 8.6931 (12) Å	T = 293 K
β = 107.129 (2)°	Block, colourless
V = 961.3 (2) Å3	0.24 × 0.22 × 0.19 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	1689 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.017
graphite	θmax = 25.0°, θmin = 2.9°
ω scans	h = −16→16
4345 measured reflections	k = −9→9
1694 independent reflections	l = −10→10

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.025	w = 1/[σ2(Fo2) + (0.043P)2 + 0.0928P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.061	(Δ/σ)max = 0.001
S = 1.15	Δρmax = 0.17 e Å−3
1694 reflections	Δρmin = −0.25 e Å−3
157 parameters	Extinction correction: SHELXTL/PC, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
2 restraints	Extinction coefficient: 0.050 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 840 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.06 (5)

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	0.29701 (12)	0.3638 (2)	0.66596 (19)	0.0342 (3)
C2	0.20184 (13)	0.3652 (2)	0.5630 (2)	0.0403 (3)
H2	0.1737	0.2705	0.5098	0.048*
C3	0.14895 (12)	0.5103 (2)	0.5403 (2)	0.0428 (4)
H3	0.0845	0.5138	0.4721	0.051*
C4	0.19244 (12)	0.6488 (2)	0.6193 (2)	0.0334 (3)
C5	0.28819 (14)	0.6483 (2)	0.7208 (2)	0.0414 (4)
H5	0.3166	0.7437	0.7723	0.050*
C6	0.34101 (13)	0.5037 (2)	0.7443 (2)	0.0424 (4)
H6	0.4055	0.5005	0.8122	0.051*
N1	0.39052 (16)	0.1289 (2)	0.8816 (2)	0.0511 (4)
N2	0.13535 (11)	0.79981 (18)	0.59414 (18)	0.0374 (3)
N3	0.55860 (12)	0.64779 (19)	0.6987 (2)	0.0447 (3)
O1	0.45798 (12)	0.21351 (19)	0.6684 (2)	0.0596 (4)
O2	0.30328 (10)	0.05499 (16)	0.60456 (18)	0.0520 (3)
O3	0.51772 (13)	0.76152 (19)	0.7468 (2)	0.0658 (4)
O4	0.53047 (11)	0.60273 (18)	0.55635 (17)	0.0557 (3)
O5	0.63098 (11)	0.57493 (19)	0.79609 (15)	0.0522 (3)
S1	0.36568 (3)	0.17908 (4)	0.69713 (4)	0.03650 (14)
H1A	0.343 (2)	0.088 (3)	0.900 (3)	0.060 (7)*
H1B	0.4231 (19)	0.194 (4)	0.932 (3)	0.056 (7)*
H1N	0.156 (2)	0.875 (4)	0.678 (4)	0.074 (8)*
H2N	0.0721 (18)	0.783 (3)	0.599 (3)	0.045 (5)*
H3N	0.1270 (18)	0.837 (3)	0.503 (3)	0.052 (6)*

	U11	U22	U33	U12	U13	U23
C1	0.0360 (7)	0.0310 (8)	0.0390 (7)	0.0001 (6)	0.0165 (6)	0.0030 (6)
C2	0.0376 (8)	0.0324 (7)	0.0484 (8)	−0.0050 (7)	0.0086 (7)	−0.0025 (7)
C3	0.0317 (7)	0.0412 (9)	0.0502 (9)	−0.0028 (6)	0.0038 (6)	0.0022 (7)
C4	0.0359 (8)	0.0308 (7)	0.0362 (7)	0.0028 (6)	0.0146 (6)	0.0036 (5)
C5	0.0417 (9)	0.0318 (8)	0.0459 (9)	−0.0015 (7)	0.0057 (7)	−0.0045 (7)
C6	0.0344 (7)	0.0372 (9)	0.0495 (9)	0.0017 (6)	0.0030 (6)	−0.0006 (6)
N1	0.0581 (10)	0.0410 (8)	0.0550 (9)	0.0039 (8)	0.0179 (8)	0.0072 (8)
N2	0.0387 (8)	0.0359 (7)	0.0399 (7)	0.0054 (6)	0.0152 (6)	0.0053 (6)
N3	0.0447 (9)	0.0421 (8)	0.0486 (9)	−0.0043 (6)	0.0154 (7)	−0.0024 (7)
O1	0.0491 (8)	0.0516 (7)	0.0924 (11)	0.0044 (6)	0.0430 (7)	0.0048 (7)
O2	0.0521 (8)	0.0368 (7)	0.0682 (8)	0.0014 (5)	0.0194 (6)	−0.0139 (6)
O3	0.0643 (9)	0.0538 (9)	0.0795 (11)	0.0092 (7)	0.0214 (7)	−0.0178 (8)
O4	0.0622 (8)	0.0551 (8)	0.0420 (6)	0.0030 (7)	0.0033 (6)	−0.0058 (6)
O5	0.0586 (8)	0.0551 (8)	0.0402 (6)	0.0095 (6)	0.0105 (5)	−0.0017 (6)
S1	0.0357 (2)	0.0304 (2)	0.0475 (2)	0.00160 (14)	0.01862 (14)	−0.00021 (15)

C1—C2	1.380 (2)	N1—S1	1.5911 (19)
C1—C6	1.382 (2)	N1—H1A	0.81 (3)
C1—S1	1.7737 (16)	N1—H1B	0.75 (3)
C2—C3	1.386 (2)	N2—H1N	0.93 (3)
C2—H2	0.9300	N2—H2N	0.92 (2)
C3—C4	1.372 (2)	N2—H3N	0.83 (3)
C3—H3	0.9300	N3—O3	1.232 (2)
C4—C5	1.382 (2)	N3—O4	1.239 (2)
C4—N2	1.457 (2)	N3—O5	1.269 (2)
C5—C6	1.382 (3)	O1—S1	1.4283 (14)
C5—H5	0.9300	O2—S1	1.4277 (14)
C6—H6	0.9300
C2—C1—C6	121.65 (15)	S1—N1—H1A	110.7 (19)
C2—C1—S1	119.47 (12)	S1—N1—H1B	109 (2)
C6—C1—S1	118.87 (13)	H1A—N1—H1B	125 (3)
C1—C2—C3	118.84 (15)	C4—N2—H1N	114.6 (19)
C1—C2—H2	120.6	C4—N2—H2N	111.9 (14)
C3—C2—H2	120.6	H1N—N2—H2N	98 (2)
C4—C3—C2	119.44 (14)	C4—N2—H3N	112.0 (17)
C4—C3—H3	120.3	H1N—N2—H3N	115 (2)
C2—C3—H3	120.3	H2N—N2—H3N	104 (2)
C3—C4—C5	121.88 (15)	O3—N3—O4	121.26 (17)
C3—C4—N2	118.52 (14)	O3—N3—O5	119.70 (17)
C5—C4—N2	119.60 (16)	O4—N3—O5	119.05 (16)
C6—C5—C4	118.85 (16)	O2—S1—O1	119.14 (9)
C6—C5—H5	120.6	O2—S1—N1	107.54 (11)
C4—C5—H5	120.6	O1—S1—N1	106.58 (11)
C5—C6—C1	119.34 (15)	O2—S1—C1	107.43 (8)
C5—C6—H6	120.3	O1—S1—C1	107.05 (8)
C1—C6—H6	120.3	N1—S1—C1	108.78 (8)
C6—C1—C2—C3	−1.1 (2)	C2—C1—C6—C5	0.8 (3)
S1—C1—C2—C3	179.76 (14)	S1—C1—C6—C5	179.95 (14)
C1—C2—C3—C4	0.5 (3)	C2—C1—S1—O2	−1.42 (15)
C2—C3—C4—C5	0.4 (3)	C6—C1—S1—O2	179.42 (14)
C2—C3—C4—N2	−179.77 (16)	C2—C1—S1—O1	127.65 (14)
C3—C4—C5—C6	−0.7 (3)	C6—C1—S1—O1	−51.51 (16)
N2—C4—C5—C6	179.48 (16)	C2—C1—S1—N1	−117.54 (15)
C4—C5—C6—C1	0.1 (3)	C6—C1—S1—N1	63.29 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.81 (3)	2.33 (3)	2.992 (2)	139 (2)
N1—H1B···O4ii	0.75 (3)	2.30 (3)	3.045 (3)	172 (3)
N2—H1N···O5iii	0.93 (3)	2.01 (3)	2.866 (2)	151 (3)
N2—H2N···O1iii	0.92 (2)	1.97 (2)	2.858 (2)	163 (2)
N2—H3N···O5iv	0.83 (3)	1.95 (3)	2.770 (2)	171 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.81 (3)	2.33 (3)	2.992 (2)	139 (2)
N1—H1B⋯O4ii	0.75 (3)	2.30 (3)	3.045 (3)	172 (3)
N2—H1N⋯O5iii	0.93 (3)	2.01 (3)	2.866 (2)	151 (3)
N2—H2N⋯O1iii	0.92 (2)	1.97 (2)	2.858 (2)	163 (2)
N2—H3N⋯O5iv	0.83 (3)	1.95 (3)	2.770 (2)	171 (2)

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