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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°].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270102003025/sk1537sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270102003025/sk1537Isup2.hkl
Contains datablock I

CCDC reference: 184488

Computing details top

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 top
Crystal data top
C6H7NO3SF(000) = 360
Mr = 173.20Dx = 1.514 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 1617 reflections
a = 7.5113 (14) Åθ = 2.8–28.7°
b = 7.2791 (13) ŵ = 0.38 mm1
c = 13.898 (3) ÅT = 120 K
V = 759.9 (3) Å3Plate, colourless
Z = 40.20 × 0.10 × 0.04 mm
Data collection top
Kappa-CCD
diffractometer
1617 independent reflections
Radiation source: fine-focus sealed X-ray tube1549 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
φ scans, and ω scans with κ offsetsθmax = 28.7°, θmin = 2.8°
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
h = 510
Tmin = 0.945, Tmax = 0.985k = 99
4761 measured reflectionsl = 1617
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.025H-atom parameters constrained
wR(F2) = 0.069 w = 1/[σ2(Fo2) + (0.0457P)2 + 0.1146P]
where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max < 0.001
1617 reflectionsΔρmax = 0.22 e Å3
100 parametersΔρmin = 0.35 e Å3
1 restraintAbsolute structure: Flack (1983), 592 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.02 (7)
Special details top

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 (Å2) top
xyzUiso*/Ueq
C10.0293 (2)0.2343 (2)0.42449 (13)0.0139 (3)
N10.05215 (19)0.2164 (2)0.32054 (11)0.0142 (3)
C20.1118 (2)0.1113 (3)0.48595 (14)0.0207 (4)
C30.0816 (2)0.1259 (3)0.58410 (13)0.0206 (4)
C40.0316 (2)0.2614 (2)0.61903 (14)0.0142 (3)
S40.08527 (5)0.26595 (4)0.74334 (4)0.01210 (11)
O410.21749 (13)0.11767 (13)0.75534 (9)0.0151 (2)
O420.07569 (15)0.22985 (17)0.79710 (11)0.0192 (3)
O430.16743 (14)0.44428 (16)0.76069 (9)0.0184 (3)
C50.1114 (2)0.3859 (3)0.55683 (13)0.0199 (4)
C60.0796 (2)0.3731 (3)0.45813 (14)0.0200 (4)
H1A0.05300.17940.28890.017*
H1B0.12470.12650.30410.017*
H1C0.09920.32110.30120.017*
H20.18800.01830.46130.025*
H30.13810.04340.62740.025*
H50.18720.47930.58130.024*
H60.13200.45830.41480.024*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0114 (7)0.0156 (8)0.0146 (8)0.0021 (5)0.0002 (6)0.0001 (6)
N10.0137 (6)0.0147 (7)0.0142 (7)0.0004 (5)0.0005 (5)0.0001 (6)
C20.0223 (8)0.0232 (9)0.0167 (9)0.0095 (7)0.0021 (7)0.0004 (7)
C30.0235 (8)0.0214 (9)0.0169 (9)0.0094 (7)0.0020 (6)0.0042 (7)
C40.0152 (7)0.0153 (8)0.0121 (8)0.0017 (6)0.0004 (6)0.0005 (6)
S40.01201 (17)0.01238 (17)0.01191 (19)0.00041 (11)0.00027 (15)0.0011 (2)
O410.0149 (5)0.0130 (5)0.0174 (6)0.0021 (4)0.0017 (5)0.0013 (5)
O420.0134 (6)0.0271 (8)0.0170 (8)0.0010 (4)0.0028 (4)0.0005 (5)
O430.0222 (5)0.0135 (5)0.0195 (7)0.0023 (4)0.0032 (5)0.0026 (5)
C50.0234 (8)0.0190 (8)0.0175 (9)0.0092 (6)0.0019 (7)0.0008 (7)
C60.0253 (9)0.0185 (9)0.0162 (9)0.0076 (7)0.0021 (6)0.0025 (7)
Geometric parameters (Å, º) top
C1—C21.384 (2)S4—O421.4454 (13)
C2—C31.387 (2)S4—O431.4574 (12)
C3—C41.389 (2)N1—H1A0.943
C4—C51.388 (2)N1—H1B0.882
C5—C61.395 (3)N1—H1C0.882
C6—C11.381 (2)C2—H20.9500
C1—N11.461 (2)C3—H30.9500
C4—S41.774 (2)C5—H50.9500
S4—O411.4762 (10)C6—H60.9500
C6—C1—C2121.97 (19)C5—C4—C3120.66 (18)
C6—C1—N1118.01 (16)C5—C4—S4119.71 (13)
C2—C1—N1119.99 (15)C3—C4—S4119.51 (14)
C1—N1—H1A112.9O42—S4—O43115.50 (8)
C1—N1—H1B113.3O42—S4—O41111.80 (7)
C1—N1—H1C105.8O43—S4—O41110.35 (6)
H1A—N1—H1B100.6O42—S4—C4108.04 (9)
H1B—N1—H1C108.3O43—S4—C4105.91 (8)
H1C—N1—H1A116.1O41—S4—C4104.43 (8)
C1—C2—C3118.94 (17)C4—C5—C6119.64 (16)
C1—C2—H2120.5C4—C5—H5120.2
C3—C2—H2120.5C6—C5—H5120.2
C2—C3—C4119.88 (17)C1—C6—C5118.87 (17)
C2—C3—H3120.1C1—C6—H6120.6
C4—C3—H3120.1C5—C6—H6120.6
C3—C4—S4—O4176.94 (14)C2—C1—N1—H1A110.8
C3—C4—S4—O4242.22 (15)C2—C1—N1—H1B2.7
C3—C4—S4—O43166.54 (13)C2—C1—N1—H1C121.2
C5—C4—S4—O4199.14 (14)C6—C1—N1—H1A67.5
C5—C4—S4—O42141.70 (13)C6—C1—N1—H1B179.0
C5—C4—S4—O4317.39 (15)C6—C1—N1—H1C60.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O41i0.941.842.767 (2)166
N1—H1B···O41ii0.882.032.877 (2)162
N1—H1B···O42iii0.882.382.816 (2)111
N1—H1C···O43iv0.881.872.746 (2)172
C3—H3···O41v0.952.393.331 (3)170
C2—H2···Cg(1)v0.953.163.949 (2)142
C5—H5···Cg(1)vi0.953.183.979 (2)143
Symmetry codes: (i) x+1/2, y, z1/2; (ii) x, y, z1/2; (iii) x1/2, y, z1/2; (iv) x, y+1, z1/2; (v) x1/2, y, z; (vi) x+1/2, y+1, z.
 

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