4-Sulfamoylanilinium perchlorate.

In the crystal of the title salt, C6H9N2O2S(+)·ClO4 (-), the components are linked by N-H⋯O hydrogen bonds, forming a three-dimensional network. The cations are connected along a and b axes, leading to linear and zigzag C(3) and C(8) chain motifs, respectively. A cation-anion inter-action along the c axis leads to a C 2 (2)(12) chain motif. R 3 (3)(18) and R 3 (3)(20) ring motifs are observed as cation-anion-type inter-actions. These hydrogen-bonding ring and chain motifs are localized at z = 0 or 1, leading to alternate hydro-philic and hydro-phobic regions along the c axis as a result of the stacking of anions and the aromatic cationic parts.

Related literature

For the first use of sulfanilamide, see: Buttle et al. (1936 ▶). For related structures, see: Ravikumar et al. (2013 ▶); Pandiarajan et al. (2011 ▶); Topacli & Kesimli (2001 ▶). For graph-set motifs, see Etter et al. (1990 ▶).

Experimental

Crystal data

C6H9N2O2S+·ClO4 −

M = 272.66

Monoclinic,

a = 4.9158 (10) Å

b = 10.514 (2) Å

c = 9.814 (2) Å

β = 93.716 (3)°

V = 506.15 (18) Å3

Z = 2

Mo Kα radiation

μ = 0.60 mm−1

T = 293 K

0.24 × 0.16 × 0.12 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

5796 measured reflections

2367 independent reflections

2361 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.022

wR(F 2) = 0.061

S = 1.08

2367 reflections

166 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.26 e Å−3

Absolute structure: Flack (1983 ▶), 1287 Friedel pairs

Flack parameter: 0.00 (4)

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/S1600536813017972/ng5332sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813017972/ng5332Isup2.hkl

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

C6H9N2O2S+·ClO4−	F(000) = 280
Mr = 272.66	Dx = 1.789 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2412 reflections
a = 4.9158 (10) Å	θ = 2.5–24.7°
b = 10.514 (2) Å	µ = 0.60 mm−1
c = 9.814 (2) Å	T = 293 K
β = 93.716 (3)°	Needle, colourless
V = 506.15 (18) Å3	0.24 × 0.16 × 0.12 mm
Z = 2

Bruker SMART APEX CCD area-detector diffractometer	2361 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
Graphite monochromator	θmax = 28.0°, θmin = 2.1°
ω scans	h = −6→6
5796 measured reflections	k = −13→13
2367 independent reflections	l = −12→12

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)] = 0.022	w = 1/[σ2(Fo2) + (0.0315P)2 + 0.1129P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.061	(Δ/σ)max = 0.001
S = 1.08	Δρmax = 0.31 e Å−3
2367 reflections	Δρmin = −0.26 e Å−3
166 parameters	Extinction correction: SHELXTL/PC (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
5 restraints	Extinction coefficient: 0.189 (7)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1287 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.00 (4)

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	0.8057 (3)	0.53210 (15)	0.53535 (15)	0.0244 (3)
C2	1.0030 (3)	0.46394 (16)	0.47189 (16)	0.0295 (3)
H2	1.0919	0.3964	0.5169	0.035*
C3	1.0672 (3)	0.49695 (19)	0.34095 (16)	0.0293 (3)
H3	1.1998	0.4523	0.2973	0.035*
C4	0.9310 (3)	0.59698 (15)	0.27676 (15)	0.0235 (3)
C5	0.7316 (3)	0.66524 (16)	0.33789 (17)	0.0281 (3)
H5	0.6419	0.7320	0.2920	0.034*
C6	0.6676 (3)	0.63237 (17)	0.46891 (17)	0.0294 (3)
H6	0.5338	0.6768	0.5119	0.035*
N1	0.9084 (3)	0.58560 (16)	0.80644 (15)	0.0315 (3)
N2	0.9994 (3)	0.63135 (15)	0.13833 (15)	0.0279 (3)
O1	0.4527 (2)	0.51671 (14)	0.71892 (14)	0.0380 (3)
O2	0.8370 (3)	0.36510 (13)	0.72799 (14)	0.0385 (3)
H1A	1.0834 (17)	0.578 (3)	0.797 (3)	0.070 (9)*
H1B	0.847 (5)	0.665 (3)	0.803 (3)	0.047 (7)*
H2A	1.120 (4)	0.584 (2)	0.100 (3)	0.055 (7)*
H2B	1.052 (5)	0.7108 (9)	0.134 (3)	0.053 (8)*
H2C	0.863 (4)	0.617 (3)	0.078 (2)	0.048 (7)*
Cl1	0.58672 (7)	0.34769 (3)	0.07752 (4)	0.02621 (11)
O3	0.8773 (2)	0.34793 (17)	0.06980 (15)	0.0409 (3)
O4	0.4686 (3)	0.26701 (16)	−0.02835 (16)	0.0477 (4)
O5	0.4874 (3)	0.47611 (13)	0.05900 (15)	0.0399 (3)
O6	0.5169 (3)	0.30181 (14)	0.20823 (15)	0.0445 (3)
S1	0.73500 (7)	0.49156 (3)	0.70441 (4)	0.02528 (11)

	U11	U22	U33	U12	U13	U23
C1	0.0265 (7)	0.0256 (7)	0.0217 (7)	−0.0006 (6)	0.0055 (5)	0.0017 (5)
C2	0.0328 (7)	0.0291 (8)	0.0268 (7)	0.0085 (6)	0.0034 (6)	0.0022 (6)
C3	0.0318 (7)	0.0310 (8)	0.0258 (7)	0.0071 (7)	0.0066 (5)	−0.0021 (6)
C4	0.0246 (6)	0.0244 (7)	0.0217 (6)	−0.0033 (5)	0.0026 (5)	0.0002 (5)
C5	0.0295 (8)	0.0260 (8)	0.0289 (7)	0.0051 (6)	0.0039 (6)	0.0046 (6)
C6	0.0286 (7)	0.0294 (8)	0.0311 (8)	0.0067 (6)	0.0091 (6)	0.0020 (7)
N1	0.0303 (7)	0.0361 (8)	0.0285 (7)	0.0003 (6)	0.0048 (6)	−0.0044 (6)
N2	0.0309 (7)	0.0293 (7)	0.0239 (6)	−0.0016 (6)	0.0045 (5)	0.0020 (6)
O1	0.0264 (6)	0.0523 (9)	0.0362 (6)	−0.0018 (5)	0.0090 (5)	0.0027 (6)
O2	0.0532 (8)	0.0281 (7)	0.0355 (6)	0.0052 (6)	0.0131 (5)	0.0080 (5)
Cl1	0.02693 (18)	0.02327 (17)	0.02901 (19)	−0.00278 (13)	0.00626 (12)	−0.00363 (14)
O3	0.0255 (6)	0.0483 (7)	0.0495 (7)	0.0003 (6)	0.0069 (5)	−0.0073 (7)
O4	0.0489 (8)	0.0478 (8)	0.0466 (9)	−0.0168 (7)	0.0033 (7)	−0.0193 (7)
O5	0.0413 (7)	0.0271 (7)	0.0522 (8)	0.0048 (6)	0.0092 (6)	0.0027 (6)
O6	0.0560 (8)	0.0424 (8)	0.0366 (7)	−0.0042 (6)	0.0155 (6)	0.0060 (6)
S1	0.02663 (18)	0.02599 (19)	0.02388 (17)	0.00010 (14)	0.00668 (12)	0.00191 (14)

C1—C2	1.386 (2)	N1—S1	1.6113 (16)
C1—C6	1.393 (2)	N1—H1A	0.875 (5)
C1—S1	1.7692 (15)	N1—H1B	0.88 (3)
C2—C3	1.387 (2)	N2—H2A	0.877 (5)
C2—H2	0.9300	N2—H2B	0.876 (5)
C3—C4	1.377 (2)	N2—H2C	0.876 (5)
C3—H3	0.9300	O1—S1	1.4289 (13)
C4—C5	1.383 (2)	O2—S1	1.4345 (14)
C4—N2	1.466 (2)	Cl1—O6	1.4328 (14)
C5—C6	1.387 (2)	Cl1—O4	1.4345 (14)
C5—H5	0.9300	Cl1—O3	1.4355 (12)
C6—H6	0.9300	Cl1—O5	1.4432 (14)
C2—C1—C6	121.01 (14)	H1A—N1—H1B	115 (3)
C2—C1—S1	118.86 (12)	C4—N2—H2A	117.2 (19)
C6—C1—S1	120.12 (12)	C4—N2—H2B	111.4 (18)
C1—C2—C3	119.67 (15)	H2A—N2—H2B	108 (3)
C1—C2—H2	120.2	C4—N2—H2C	111.9 (18)
C3—C2—H2	120.2	H2A—N2—H2C	97 (3)
C4—C3—C2	118.80 (15)	H2B—N2—H2C	110 (3)
C4—C3—H3	120.6	O6—Cl1—O4	109.89 (10)
C2—C3—H3	120.6	O6—Cl1—O3	110.16 (9)
C3—C4—C5	122.36 (15)	O4—Cl1—O3	108.68 (9)
C3—C4—N2	118.57 (14)	O6—Cl1—O5	109.20 (9)
C5—C4—N2	119.06 (14)	O4—Cl1—O5	110.13 (10)
C4—C5—C6	118.85 (14)	O3—Cl1—O5	108.75 (9)
C4—C5—H5	120.6	O1—S1—O2	119.15 (9)
C6—C5—H5	120.6	O1—S1—N1	107.62 (8)
C5—C6—C1	119.31 (14)	O2—S1—N1	107.65 (9)
C5—C6—H6	120.3	O1—S1—C1	107.46 (7)
C1—C6—H6	120.3	O2—S1—C1	106.66 (7)
S1—N1—H1A	111 (2)	N1—S1—C1	107.86 (8)
S1—N1—H1B	112.7 (17)
C6—C1—C2—C3	0.9 (3)	C2—C1—C6—C5	−0.8 (2)
S1—C1—C2—C3	−177.99 (13)	S1—C1—C6—C5	178.07 (13)
C1—C2—C3—C4	−0.3 (3)	C2—C1—S1—O1	−147.96 (13)
C2—C3—C4—C5	−0.3 (3)	C6—C1—S1—O1	33.10 (16)
C2—C3—C4—N2	−179.92 (15)	C2—C1—S1—O2	−19.12 (16)
C3—C4—C5—C6	0.4 (2)	C6—C1—S1—O2	161.93 (14)
N2—C4—C5—C6	−179.99 (15)	C2—C1—S1—N1	96.28 (15)
C4—C5—C6—C1	0.2 (2)	C6—C1—S1—N1	−82.67 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.88 (1)	2.12 (1)	2.953 (2)	160 (3)
N1—H1B···O6ii	0.88 (3)	2.30 (3)	3.086 (2)	149 (2)
N2—H2A···O5i	0.88 (1)	2.19 (1)	3.044 (2)	164 (3)
N2—H2B···O2iii	0.88 (1)	2.16 (2)	2.876 (2)	139 (2)
N2—H2C···O4iv	0.88 (1)	2.30 (2)	2.858 (2)	122 (2)
N2—H2C···O5	0.88 (1)	2.37 (2)	3.058 (2)	136 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.88 (1)	2.12 (1)	2.953 (2)	160 (3)
N1—H1B⋯O6ii	0.88 (3)	2.30 (3)	3.086 (2)	149 (2)
N2—H2A⋯O5i	0.88 (1)	2.19 (1)	3.044 (2)	164 (3)
N2—H2B⋯O2iii	0.88 (1)	2.16 (2)	2.876 (2)	139 (2)
N2—H2C⋯O4iv	0.88 (1)	2.30 (2)	2.858 (2)	122 (2)
N2—H2C⋯O5	0.88 (1)	2.37 (2)	3.058 (2)	136 (2)

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