A quasi-diamondoid hydrogen-bonded framework in an­hydro­us sulfanilic acid

The title compound (C₆H₇NO₃S) exists as a zwitterion (4-ammonio­benzene­sulfonate), ⁺H₃NC₆H₄SO₃^-, and these units are linked into a three-dimensional framework by two distinct two-centre N-H...O hydrogen bonds [H...O 1.84 and 1.87 Å; N...O 2.767 (2) and 2.746 (2) Å; N-H...O 166 and 172°] and a planar three-centre N-H...(O)₂ hydrogen bond [H...O 2.03 and 2.37 Å; N...O 2.816 (2) and 2.877 (2) Å; N-H...O 162 and 111°; O...H...O 86°].

Computing details

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2002); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PRPKAPPA (Ferguson, 1999).

4-Aminobenzenesulfonic acid

Crystal data

C6H7NO3S	F(000) = 360
Mr = 173.20	Dx = 1.514 Mg m^−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 1617 reflections
a = 7.5113 (14) Å	θ = 2.8–28.7°
b = 7.2791 (13) Å	µ = 0.38 mm^−1
c = 13.898 (3) Å	T = 120 K
V = 759.9 (3) Å^3	Plate, colourless
Z = 4	0.20 × 0.10 × 0.04 mm

Data collection

Kappa-CCD diffractometer	1617 independent reflections
Radiation source: fine-focus sealed X-ray tube	1549 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
φ scans, and ω scans with κ offsets	θmax = 28.7°, θmin = 2.8°
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	h = −5→10
Tmin = 0.945, Tmax = 0.985	k = −9→9
4761 measured reflections	l = −16→17

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.025	H-atom parameters constrained
wR(F^2) = 0.069	w = 1/[σ^2(Fo^2) + (0.0457P)^2 + 0.1146P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max < 0.001
1617 reflections	Δρmax = 0.22 e Å^−3
100 parameters	Δρmin = −0.35 e Å^−3
1 restraint	Absolute structure: Flack (1983), 592 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (7)

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891]which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	−0.0293 (2)	0.2343 (2)	0.42449 (13)	0.0139 (3)
N1	−0.05215 (19)	0.2164 (2)	0.32054 (11)	0.0142 (3)
C2	−0.1118 (2)	0.1113 (3)	0.48595 (14)	0.0207 (4)
C3	−0.0816 (2)	0.1259 (3)	0.58410 (13)	0.0206 (4)
C4	0.0316 (2)	0.2614 (2)	0.61903 (14)	0.0142 (3)
S4	0.08527 (5)	0.26595 (4)	0.74334 (4)	0.01210 (11)
O41	0.21749 (13)	0.11767 (13)	0.75534 (9)	0.0151 (2)
O42	−0.07569 (15)	0.22985 (17)	0.79710 (11)	0.0192 (3)
O43	0.16743 (14)	0.44428 (16)	0.76069 (9)	0.0184 (3)
C5	0.1114 (2)	0.3859 (3)	0.55683 (13)	0.0199 (4)
C6	0.0796 (2)	0.3731 (3)	0.45813 (14)	0.0200 (4)
H1A	0.0530	0.1794	0.2889	0.017*
H1B	−0.1247	0.1265	0.3041	0.017*
H1C	−0.0992	0.3211	0.3012	0.017*
H2	−0.1880	0.0183	0.4613	0.025*
H3	−0.1381	0.0434	0.6274	0.025*
H5	0.1872	0.4793	0.5813	0.024*
H6	0.1320	0.4583	0.4148	0.024*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0114 (7)	0.0156 (8)	0.0146 (8)	0.0021 (5)	0.0002 (6)	0.0001 (6)
N1	0.0137 (6)	0.0147 (7)	0.0142 (7)	0.0004 (5)	−0.0005 (5)	0.0001 (6)
C2	0.0223 (8)	0.0232 (9)	0.0167 (9)	−0.0095 (7)	−0.0021 (7)	0.0004 (7)
C3	0.0235 (8)	0.0214 (9)	0.0169 (9)	−0.0094 (7)	−0.0020 (6)	0.0042 (7)
C4	0.0152 (7)	0.0153 (8)	0.0121 (8)	0.0017 (6)	−0.0004 (6)	0.0005 (6)
S4	0.01201 (17)	0.01238 (17)	0.01191 (19)	0.00041 (11)	−0.00027 (15)	−0.0011 (2)
O41	0.0149 (5)	0.0130 (5)	0.0174 (6)	0.0021 (4)	−0.0017 (5)	−0.0013 (5)
O42	0.0134 (6)	0.0271 (8)	0.0170 (8)	−0.0010 (4)	0.0028 (4)	−0.0005 (5)
O43	0.0222 (5)	0.0135 (5)	0.0195 (7)	−0.0023 (4)	−0.0032 (5)	−0.0026 (5)
C5	0.0234 (8)	0.0190 (8)	0.0175 (9)	−0.0092 (6)	−0.0019 (7)	0.0008 (7)
C6	0.0253 (9)	0.0185 (9)	0.0162 (9)	−0.0076 (7)	0.0021 (6)	0.0025 (7)

Geometric parameters (Å, º)

C1—C2	1.384 (2)	S4—O42	1.4454 (13)
C2—C3	1.387 (2)	S4—O43	1.4574 (12)
C3—C4	1.389 (2)	N1—H1A	0.943
C4—C5	1.388 (2)	N1—H1B	0.882
C5—C6	1.395 (3)	N1—H1C	0.882
C6—C1	1.381 (2)	C2—H2	0.9500
C1—N1	1.461 (2)	C3—H3	0.9500
C4—S4	1.774 (2)	C5—H5	0.9500
S4—O41	1.4762 (10)	C6—H6	0.9500
C6—C1—C2	121.97 (19)	C5—C4—C3	120.66 (18)
C6—C1—N1	118.01 (16)	C5—C4—S4	119.71 (13)
C2—C1—N1	119.99 (15)	C3—C4—S4	119.51 (14)
C1—N1—H1A	112.9	O42—S4—O43	115.50 (8)
C1—N1—H1B	113.3	O42—S4—O41	111.80 (7)
C1—N1—H1C	105.8	O43—S4—O41	110.35 (6)
H1A—N1—H1B	100.6	O42—S4—C4	108.04 (9)
H1B—N1—H1C	108.3	O43—S4—C4	105.91 (8)
H1C—N1—H1A	116.1	O41—S4—C4	104.43 (8)
C1—C2—C3	118.94 (17)	C4—C5—C6	119.64 (16)
C1—C2—H2	120.5	C4—C5—H5	120.2
C3—C2—H2	120.5	C6—C5—H5	120.2
C2—C3—C4	119.88 (17)	C1—C6—C5	118.87 (17)
C2—C3—H3	120.1	C1—C6—H6	120.6
C4—C3—H3	120.1	C5—C6—H6	120.6
C3—C4—S4—O41	76.94 (14)	C2—C1—N1—H1A	−110.8
C3—C4—S4—O42	−42.22 (15)	C2—C1—N1—H1B	2.7
C3—C4—S4—O43	−166.54 (13)	C2—C1—N1—H1C	121.2
C5—C4—S4—O41	−99.14 (14)	C6—C1—N1—H1A	67.5
C5—C4—S4—O42	141.70 (13)	C6—C1—N1—H1B	−179.0
C5—C4—S4—O43	17.39 (15)	C6—C1—N1—H1C	−60.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O41^i	0.94	1.84	2.767 (2)	166
N1—H1B···O41^ii	0.88	2.03	2.877 (2)	162
N1—H1B···O42^iii	0.88	2.38	2.816 (2)	111
N1—H1C···O43^iv	0.88	1.87	2.746 (2)	172
C3—H3···O41^v	0.95	2.39	3.331 (3)	170
C2—H2···Cg(1)^v	0.95	3.16	3.949 (2)	142
C5—H5···Cg(1)^vi	0.95	3.18	3.979 (2)	143

Symmetry codes: (i) −x+1/2, y, z−1/2; (ii) −x, −y, z−1/2; (iii) −x−1/2, y, z−1/2; (iv) −x, −y+1, z−1/2; (v) x−1/2, −y, z; (vi) x+1/2, −y+1, z.