4-Sulfamoylanilinium chloride.

In the crystal structure of the title compound, C(6)H(9)N(2)O(2)S(+)·Cl(-), the chloride anions are sandwiched between layers of 4-sulfonamido-anilinium anions. The components interact by way of N-H⋯Cl and N-H⋯O hydrogen bonds, building up a three-dimensional network.

Related literature

For the biological activity of diamines, see: Pasini & Zunino (1987 ▶); Otsuka et al. (1990 ▶); Michalson & Smuszkovicz (1989 ▶); Reedijk et al. (1996 ▶). For their use in asymmetric catalysis, see: Blaser (1992 ▶). For related structures, see: Chatterjee et al. (1981 ▶); Gelbrich et al. (2008 ▶); Gelmboldt et al. (2004 ▶); Smith et al. (2001 ▶).

Experimental

Crystal data

C6H9N2O2S+·Cl−

M = 208.66

Orthorhombic,

a = 7.4608 (2) Å

b = 7.7278 (2) Å

c = 31.694 (2) Å

V = 1827.35 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.61 mm−1

T = 298 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.982, T max = 0.994

2906 measured reflections

1989 independent reflections

1442 reflections with I > 2σ(I)

R int = 0.033

2 standard reflections every 120 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.182

S = 1.07

1989 reflections

110 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.44 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810019471/dn2568sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810019471/dn2568Isup2.hkl

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

C6H9N2O2S+·Cl−	F(000) = 864
Mr = 208.66	Dx = 1.517 Mg m−3
Orthorhombic, Pbnb	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2bc 2ab	Cell parameters from 25 reflections
a = 7.4608 (2) Å	θ = 10–15°
b = 7.7278 (2) Å	µ = 0.61 mm−1
c = 31.694 (2) Å	T = 298 K
V = 1827.35 (13) Å3	Prism, colourless
Z = 8	0.3 × 0.2 × 0.1 mm

Enraf–Nonius CAD-4 diffractometer	1442 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
graphite	θmax = 27.0°, θmin = 2.6°
Non–profiled ω/2θ scans	h = −9→2
Absorption correction: ψ scan (North et al., 1968)	k = −1→9
Tmin = 0.982, Tmax = 0.994	l = −1→40
2906 measured reflections	2 standard reflections every 120 min
1989 independent reflections	intensity decay: none

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.182	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.1231P)2 + 0.2341P] where P = (Fo2 + 2Fc2)/3
1989 reflections	(Δ/σ)max = 0.001
110 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.44 e Å−3

Experimental. Number of psi-scan sets used was 5 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied (North et al., 1968).

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	−0.01848 (14)	0.91801 (12)	0.80899 (3)	0.0494 (3)
O1	0.0885 (5)	1.0213 (4)	0.78197 (10)	0.0826 (11)
O2	−0.1835 (5)	0.9862 (4)	0.82564 (9)	0.0718 (10)
N1	0.4306 (4)	0.7241 (3)	0.95815 (9)	0.0394 (6)
H1A	0.4863	0.8185	0.9675	0.059*
H1B	0.5114	0.6443	0.9512	0.059*
H1C	0.3596	0.6828	0.9783	0.059*
N2	−0.0703 (5)	0.7452 (5)	0.78407 (10)	0.0623 (9)
H21	0.0127	0.7023	0.7694	0.075*
H22	−0.1381	0.6733	0.7963	0.075*
C1	0.3224 (4)	0.7679 (3)	0.92096 (9)	0.0317 (6)
C2	0.1373 (4)	0.7587 (4)	0.92407 (10)	0.0402 (7)
H2	0.0833	0.7210	0.9489	0.048*
C3	0.0345 (4)	0.8064 (5)	0.88976 (10)	0.0433 (7)
H3	−0.0898	0.8026	0.8915	0.052*
C4	0.1162 (4)	0.8597 (4)	0.85296 (9)	0.0368 (7)
C5	0.3026 (5)	0.8677 (4)	0.84957 (11)	0.0438 (8)
H5	0.3563	0.9039	0.8246	0.053*
C6	0.4060 (4)	0.8208 (4)	0.88399 (11)	0.0444 (7)
H6	0.5304	0.8246	0.8824	0.053*
Cl1	0.72981 (10)	1.00078 (9)	0.97197 (3)	0.0408 (3)

	U11	U22	U33	U12	U13	U23
S1	0.0590 (6)	0.0496 (5)	0.0396 (5)	0.0060 (4)	−0.0092 (4)	0.0052 (4)
O1	0.097 (3)	0.084 (2)	0.066 (2)	−0.0156 (19)	−0.015 (2)	0.0379 (16)
O2	0.0707 (18)	0.084 (2)	0.0607 (19)	0.0399 (17)	−0.0180 (16)	−0.0076 (15)
N1	0.0340 (12)	0.0321 (13)	0.0521 (16)	−0.0016 (10)	−0.0096 (11)	0.0030 (11)
N2	0.067 (2)	0.075 (2)	0.0450 (17)	−0.0057 (18)	−0.0046 (16)	−0.0158 (15)
C1	0.0284 (12)	0.0237 (12)	0.0432 (16)	0.0010 (11)	−0.0005 (12)	−0.0017 (11)
C2	0.0327 (15)	0.0508 (17)	0.0373 (15)	−0.0017 (14)	0.0024 (12)	0.0058 (13)
C3	0.0273 (13)	0.0593 (19)	0.0431 (18)	0.0005 (14)	−0.0008 (13)	0.0031 (15)
C4	0.0395 (16)	0.0311 (14)	0.0397 (17)	0.0025 (12)	−0.0044 (13)	−0.0011 (12)
C5	0.0416 (17)	0.0449 (18)	0.0450 (19)	−0.0025 (14)	0.0098 (13)	0.0050 (14)
C6	0.0306 (14)	0.0488 (18)	0.0536 (19)	−0.0019 (14)	0.0052 (14)	0.0001 (15)
Cl1	0.0310 (4)	0.0328 (5)	0.0586 (6)	−0.0038 (3)	0.0016 (3)	0.0013 (3)

S1—O1	1.417 (3)	C1—C2	1.386 (4)
S1—O2	1.439 (4)	C1—C6	1.389 (4)
S1—N2	1.599 (3)	C2—C3	1.381 (4)
S1—C4	1.776 (3)	C2—H2	0.9300
N1—C1	1.468 (4)	C3—C4	1.379 (4)
N1—H1A	0.8900	C3—H3	0.9300
N1—H1B	0.8900	C4—C5	1.396 (5)
N1—H1C	0.8900	C5—C6	1.384 (5)
N2—H21	0.8433	C5—H5	0.9300
N2—H22	0.8457	C6—H6	0.9300
O1—S1—O2	119.8 (2)	C6—C1—N1	119.9 (3)
O1—S1—N2	107.9 (2)	C3—C2—C1	118.9 (3)
O2—S1—N2	106.3 (2)	C3—C2—H2	120.5
O1—S1—C4	107.35 (18)	C1—C2—H2	120.5
O2—S1—C4	106.81 (16)	C4—C3—C2	120.0 (3)
N2—S1—C4	108.23 (17)	C4—C3—H3	120.0
C1—N1—H1A	109.5	C2—C3—H3	120.0
C1—N1—H1B	109.5	C3—C4—C5	121.2 (3)
H1A—N1—H1B	109.5	C3—C4—S1	119.3 (2)
C1—N1—H1C	109.5	C5—C4—S1	119.5 (2)
H1A—N1—H1C	109.5	C6—C5—C4	118.9 (3)
H1B—N1—H1C	109.5	C6—C5—H5	120.5
S1—N2—H21	115.1	C4—C5—H5	120.5
S1—N2—H22	117.9	C5—C6—C1	119.4 (3)
H21—N2—H22	115.7	C5—C6—H6	120.3
C2—C1—C6	121.5 (3)	C1—C6—H6	120.3
C2—C1—N1	118.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1	0.89	2.30	3.122 (3)	153
N1—H1B···Cl1i	0.89	2.32	3.097 (3)	146
N1—H1C···Cl1ii	0.89	2.33	3.189 (3)	162
N2—H21···O1iii	0.84	2.22	2.963 (5)	147
N2—H22···O2iv	0.85	2.17	3.019 (5)	178

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl1	0.89	2.30	3.122 (3)	153
N1—H1B⋯Cl1i	0.89	2.32	3.097 (3)	146
N1—H1C⋯Cl1ii	0.89	2.33	3.189 (3)	162
N2—H21⋯O1iii	0.84	2.22	2.963 (5)	147
N2—H22⋯O2iv	0.85	2.17	3.019 (5)	178

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