2-(4-Sulfamoylphen-yl)hydrazin-1-ium chloride.

The hydrazinium residue in the cation of the title salt, C(6)H(10)N(3)O(2)S(+)·Cl(-), is twisted out of the plane of the benzene ring to which it is attached [N-N-C-C torsion angle = 25.9 (2)°] and the amino group is almost perpendicular to the benzene ring [N-S-C-C torsion angle = 88.71 (16)°]. In the crystal, the cations are linked by N-H⋯O hydrogen bonds and π-π inter-actions [ring centroid distance = 3.7280 (11) Å], forming layers in the bc plane that are connected by N-H⋯Cl hydrogen bonds.

Related literature

For background to the biological applications of related sulfonamides, see: Croitoru et al. (2004 ▶); Dogruer et al. (2010 ▶). For related structures, see: Asiri et al. (2011 ▶, 2012 ▶).

Experimental

Crystal data

C6H10N3O2S+·Cl−

M = 223.68

Monoclinic,

a = 10.2203 (8) Å

b = 9.8883 (7) Å

c = 9.1948 (8) Å

β = 107.647 (9)°

V = 885.51 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.64 mm−1

T = 100 K

0.35 × 0.30 × 0.25 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.808, T max = 0.857

3570 measured reflections

2026 independent reflections

1767 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.084

S = 1.03

2026 reflections

142 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.43 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812011452/hb6680sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812011452/hb6680Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812011452/hb6680Isup3.cml

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

C6H10N3O2S+·Cl−	F(000) = 464
Mr = 223.68	Dx = 1.678 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2194 reflections
a = 10.2203 (8) Å	θ = 2.3–27.5°
b = 9.8883 (7) Å	µ = 0.64 mm−1
c = 9.1948 (8) Å	T = 100 K
β = 107.647 (9)°	Irregular, light-brown
V = 885.51 (12) Å3	0.35 × 0.30 × 0.25 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	2026 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1767 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.024
Detector resolution: 10.4041 pixels mm-1	θmax = 27.5°, θmin = 2.9°
ω scan	h = −13→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −12→12
Tmin = 0.808, Tmax = 0.857	l = −9→11
3570 measured reflections

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0404P)2 + 0.3504P] where P = (Fo2 + 2Fc2)/3
2026 reflections	(Δ/σ)max < 0.001
142 parameters	Δρmax = 0.39 e Å−3
6 restraints	Δρmin = −0.43 e Å−3

	x	y	z	Uiso*/Ueq
Cl1	0.86073 (5)	−0.03338 (4)	0.61107 (5)	0.01345 (14)
S1	0.21204 (4)	0.40936 (4)	0.48750 (5)	0.00899 (13)
O1	0.17687 (13)	0.36536 (13)	0.33148 (14)	0.0118 (3)
N3	0.13229 (16)	0.31234 (16)	0.57265 (18)	0.0114 (3)
N1	0.89021 (16)	0.26661 (17)	0.72569 (19)	0.0124 (3)
N2	0.80635 (16)	0.32732 (16)	0.80730 (17)	0.0119 (3)
O2	0.18027 (13)	0.54566 (12)	0.51886 (15)	0.0129 (3)
C1	0.38970 (18)	0.38531 (18)	0.5743 (2)	0.0095 (4)
C2	0.46066 (19)	0.28593 (18)	0.5230 (2)	0.0112 (4)
H2A	0.4148	0.2318	0.4374	0.013*
C3	0.59980 (19)	0.26604 (18)	0.5979 (2)	0.0108 (4)
H3A	0.6489	0.1979	0.5635	0.013*
C4	0.66731 (18)	0.34606 (18)	0.7235 (2)	0.0094 (4)
C5	0.59489 (19)	0.44578 (18)	0.7736 (2)	0.0119 (4)
H5A	0.6405	0.5005	0.8588	0.014*
C6	0.45657 (19)	0.46530 (18)	0.6994 (2)	0.0118 (4)
H6A	0.4073	0.5333	0.7338	0.014*
H1	0.874 (2)	0.1789 (11)	0.710 (3)	0.021 (6)*
H2	0.879 (2)	0.302 (2)	0.6347 (16)	0.027 (7)*
H3	0.9755 (12)	0.284 (2)	0.779 (2)	0.030 (7)*
H4	0.842 (2)	0.4043 (16)	0.851 (3)	0.032 (7)*
H5	0.145 (3)	0.339 (2)	0.6667 (14)	0.029 (7)*
H6	0.148 (2)	0.2263 (11)	0.564 (3)	0.024 (6)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0161 (2)	0.0110 (2)	0.0118 (2)	0.00202 (17)	0.00197 (18)	0.00096 (16)
S1	0.0077 (2)	0.0090 (2)	0.0098 (2)	0.00040 (16)	0.00203 (17)	0.00041 (16)
O1	0.0122 (6)	0.0137 (6)	0.0087 (6)	−0.0005 (5)	0.0018 (5)	0.0004 (5)
N3	0.0117 (8)	0.0114 (8)	0.0114 (8)	−0.0016 (6)	0.0041 (6)	−0.0003 (6)
N1	0.0074 (8)	0.0142 (8)	0.0154 (8)	0.0007 (6)	0.0030 (7)	−0.0008 (7)
N2	0.0094 (7)	0.0115 (7)	0.0133 (8)	0.0004 (6)	0.0014 (6)	−0.0020 (6)
O2	0.0119 (6)	0.0097 (6)	0.0163 (7)	0.0020 (5)	0.0029 (5)	0.0001 (5)
C1	0.0077 (8)	0.0104 (8)	0.0105 (9)	−0.0006 (7)	0.0028 (7)	0.0019 (7)
C2	0.0110 (8)	0.0108 (8)	0.0112 (9)	−0.0022 (7)	0.0025 (7)	−0.0017 (7)
C3	0.0105 (8)	0.0094 (8)	0.0135 (9)	0.0011 (7)	0.0052 (7)	0.0002 (7)
C4	0.0077 (8)	0.0096 (8)	0.0104 (8)	0.0002 (7)	0.0020 (7)	0.0043 (7)
C5	0.0136 (9)	0.0104 (8)	0.0106 (9)	−0.0011 (7)	0.0020 (7)	−0.0020 (7)
C6	0.0122 (9)	0.0111 (9)	0.0125 (9)	0.0009 (7)	0.0044 (7)	−0.0008 (7)

S1—O2	1.4358 (13)	N2—H4	0.887 (10)
S1—O1	1.4366 (13)	C1—C2	1.386 (3)
S1—N3	1.6076 (16)	C1—C6	1.392 (3)
S1—C1	1.7640 (18)	C2—C3	1.393 (3)
N3—H5	0.876 (10)	C2—H2A	0.9500
N3—H6	0.873 (10)	C3—C4	1.397 (3)
N1—N2	1.431 (2)	C3—H3A	0.9500
N1—H1	0.886 (10)	C4—C5	1.392 (3)
N1—H2	0.883 (10)	C5—C6	1.384 (3)
N1—H3	0.877 (10)	C5—H5A	0.9500
N2—C4	1.408 (2)	C6—H6A	0.9500
O2—S1—O1	118.78 (8)	C2—C1—C6	120.49 (16)
O2—S1—N3	106.47 (8)	C2—C1—S1	120.96 (14)
O1—S1—N3	107.17 (8)	C6—C1—S1	118.52 (14)
O2—S1—C1	107.46 (8)	C1—C2—C3	119.51 (16)
O1—S1—C1	108.83 (8)	C1—C2—H2A	120.2
N3—S1—C1	107.66 (8)	C3—C2—H2A	120.2
S1—N3—H5	110.8 (16)	C2—C3—C4	120.19 (17)
S1—N3—H6	113.8 (16)	C2—C3—H3A	119.9
H5—N3—H6	114 (2)	C4—C3—H3A	119.9
N2—N1—H1	112.5 (15)	C5—C4—C3	119.70 (16)
N2—N1—H2	113.9 (15)	C5—C4—N2	117.49 (16)
H1—N1—H2	106 (2)	C3—C4—N2	122.76 (16)
N2—N1—H3	106.2 (16)	C6—C5—C4	120.12 (17)
H1—N1—H3	113 (2)	C6—C5—H5A	119.9
H2—N1—H3	106 (2)	C4—C5—H5A	119.9
C4—N2—N1	115.70 (14)	C5—C6—C1	120.00 (17)
C4—N2—H4	110.0 (16)	C5—C6—H6A	120.0
N1—N2—H4	111.8 (17)	C1—C6—H6A	120.0
O2—S1—C1—C2	−156.96 (14)	C2—C3—C4—C5	0.0 (3)
O1—S1—C1—C2	−27.13 (17)	C2—C3—C4—N2	177.52 (17)
N3—S1—C1—C2	88.71 (16)	N1—N2—C4—C5	−156.52 (16)
O2—S1—C1—C6	25.25 (17)	N1—N2—C4—C3	25.9 (2)
O1—S1—C1—C6	155.08 (14)	C3—C4—C5—C6	0.1 (3)
N3—S1—C1—C6	−89.07 (16)	N2—C4—C5—C6	−177.47 (17)
C6—C1—C2—C3	0.3 (3)	C4—C5—C6—C1	−0.1 (3)
S1—C1—C2—C3	−177.48 (14)	C2—C1—C6—C5	−0.1 (3)
C1—C2—C3—C4	−0.2 (3)	S1—C1—C6—C5	177.71 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1	0.89 (1)	2.28 (1)	3.1319 (17)	162 (2)
N1—H2···O2i	0.88 (2)	2.03 (2)	2.835 (2)	152 (2)
N1—H3···Cl1ii	0.88 (2)	2.46 (2)	3.2136 (18)	144 (2)
N1—H3···O1iii	0.88 (2)	2.46 (2)	3.083 (2)	129 (2)
N2—H4···Cl1iv	0.89 (2)	2.67 (2)	3.3647 (16)	137 (2)
N3—H5···Cl1v	0.88 (1)	2.42 (2)	3.2656 (17)	163 (2)
N3—H6···Cl1vi	0.87 (1)	2.48 (2)	3.2467 (17)	147 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl1	0.89 (1)	2.28 (1)	3.1319 (17)	162 (2)
N1—H2⋯O2i	0.88 (2)	2.03 (2)	2.835 (2)	152 (2)
N1—H3⋯Cl1ii	0.88 (2)	2.46 (2)	3.2136 (18)	144 (2)
N1—H3⋯O1iii	0.88 (2)	2.46 (2)	3.083 (2)	129 (2)
N2—H4⋯Cl1iv	0.89 (2)	2.67 (2)	3.3647 (16)	137 (2)
N3—H5⋯Cl1v	0.88 (1)	2.42 (2)	3.2656 (17)	163 (2)
N3—H6⋯Cl1vi	0.87 (1)	2.48 (2)	3.2467 (17)	147 (2)

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