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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3281.
Published online 2010 November 24. doi:  10.1107/S1600536810048063
PMCID: PMC3011372

4-Amino-3-ammonio­benzene­sulfonate

Abstract

The title compound, C6H8N2O3S, crystallized as a sulfonate–aminium zwitterion. In the crystal, inter­molecular N—H(...)O hydrogen bonds generate an extensive three-dimensional network, which consolidates the packing.

Related literature

For the crystal structures of isomers of the title compound, see: Rubin-Preminger & Bernstein (2003 [triangle]). For details of the synthesis, see: Miranda et al. (2008 [triangle]).

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Object name is e-66-o3281-scheme1.jpg

Experimental

Crystal data

  • C6H8N2O3S
  • M r = 188.20
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3281-efi1.jpg
  • a = 5.602 (1) Å
  • b = 8.4135 (15) Å
  • c = 16.221 (3) Å
  • β = 95.613 (2)°
  • V = 760.9 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.39 mm−1
  • T = 295 K
  • 0.35 × 0.25 × 0.15 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.875, T max = 0.944
  • 4039 measured reflections
  • 1490 independent reflections
  • 1351 reflections with I > 2σ(I)
  • R int = 0.019

Refinement

  • R[F 2 > 2σ(F 2)] = 0.031
  • wR(F 2) = 0.087
  • S = 1.09
  • 1490 reflections
  • 122 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.34 e Å−3
  • Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810048063/cv2799sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048063/cv2799Isup2.hkl

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

supplementary crystallographic information

Comment

The title compound (I) (Fig. 1) is a zwitterion of 4-amino-3-ammoniobenzenesulfonate. The bond lengths and angles in (I) are normal and comparable with those observed in the related compounds (Rubin-Preminger & Bernstein, 2003). In the crystal structure, intermolecular N—H···O hydrogen bonds generate an extensive three-dumensional network which consolidate the crystal packing.

Experimental

The title compound was synthesized according to the method reported in the literature (Miranda et al., 2008). Orange single crystals suitable for X-ray diffraction were obtained by slow evaporation of a water solution of the compound.

Refinement

C-bound H atoms and N(amino)-bound H atoms were geometrically positioned (C—H = 0.93 Å, N—H = 0.86 Å) and included in the riding model approximation, with Uiso(H) = 1.2 Ueq(C, N). H atoms attached to N(ammonio) were located from an electron density map, and isotropically refined with the N—H bond length restrained to 0.91 (3) Å.

Figures

Fig. 1.
The molecular structure of (I), with displacement ellipsoids drawn at the 30% probability level.

Crystal data

C6H8N2O3SF(000) = 392
Mr = 188.20Dx = 1.643 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2332 reflections
a = 5.602 (1) Åθ = 2.4–27.7°
b = 8.4135 (15) ŵ = 0.39 mm1
c = 16.221 (3) ÅT = 295 K
β = 95.613 (2)°Block, orange
V = 760.9 (2) Å30.35 × 0.25 × 0.15 mm
Z = 4

Data collection

Bruker SMART APEXII CCD area-detector diffractometer1490 independent reflections
Radiation source: fine-focus sealed tube1351 reflections with I > 2σ(I)
graphiteRint = 0.019
phi and ω scansθmax = 26.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −6→6
Tmin = 0.875, Tmax = 0.944k = −9→10
4039 measured reflectionsl = −17→19

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.087w = 1/[σ2(Fo2) + (0.0446P)2 + 0.3348P] where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
1490 reflectionsΔρmax = 0.34 e Å3
122 parametersΔρmin = −0.33 e Å3
0 restraintsExtinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.022 (3)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
C10.1329 (3)0.2272 (2)1.04906 (10)0.0265 (4)
C20.1963 (3)0.15996 (19)0.97641 (10)0.0263 (4)
H20.33480.09880.97690.032*
C30.0532 (3)0.18407 (19)0.90339 (10)0.0263 (4)
C4−0.1567 (3)0.2754 (2)0.90017 (10)0.0300 (4)
C5−0.2178 (3)0.3403 (2)0.97466 (11)0.0341 (4)
H5−0.35700.40050.97470.041*
C6−0.0764 (3)0.3168 (2)1.04811 (11)0.0314 (4)
H6−0.12070.36081.09700.038*
H1A0.266 (4)0.065 (3)0.8377 (14)0.052 (7)*
H1B0.132 (4)0.185 (3)0.7858 (16)0.045 (6)*
H1C0.012 (4)0.033 (3)0.8111 (15)0.055 (7)*
N10.1219 (3)0.1112 (2)0.82725 (9)0.0304 (3)
N2−0.2985 (3)0.3022 (2)0.82732 (11)0.0502 (5)
H2B−0.42600.35920.82740.060*
H2A−0.25970.26190.78180.060*
O10.1572 (3)0.16078 (16)1.20518 (8)0.0413 (4)
O20.4779 (3)0.07161 (18)1.12735 (8)0.0518 (4)
O30.4413 (2)0.34942 (17)1.16250 (8)0.0424 (4)
S10.31916 (8)0.20155 (5)1.14202 (2)0.02874 (18)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0281 (9)0.0290 (8)0.0218 (8)0.0004 (6)−0.0011 (6)−0.0005 (6)
C20.0269 (8)0.0274 (8)0.0243 (8)0.0028 (6)0.0004 (6)0.0009 (6)
C30.0302 (9)0.0259 (8)0.0222 (8)0.0004 (6)0.0005 (6)−0.0006 (6)
C40.0303 (9)0.0298 (8)0.0285 (9)0.0012 (7)−0.0045 (7)0.0012 (7)
C50.0277 (9)0.0369 (9)0.0368 (10)0.0073 (7)−0.0004 (7)−0.0027 (7)
C60.0309 (9)0.0363 (9)0.0275 (9)0.0036 (7)0.0045 (7)−0.0054 (7)
N10.0352 (9)0.0334 (8)0.0217 (7)0.0054 (7)−0.0010 (6)−0.0001 (6)
N20.0538 (11)0.0559 (11)0.0364 (9)0.0241 (9)−0.0188 (8)−0.0073 (8)
O10.0556 (9)0.0457 (8)0.0228 (6)−0.0086 (6)0.0054 (6)−0.0029 (5)
O20.0625 (9)0.0574 (9)0.0324 (7)0.0326 (8)−0.0104 (6)−0.0080 (6)
O30.0452 (8)0.0432 (8)0.0366 (7)−0.0086 (6)−0.0072 (6)−0.0032 (6)
S10.0343 (3)0.0307 (3)0.0203 (2)0.00447 (16)−0.00195 (17)−0.00273 (15)

Geometric parameters (Å, °)

C1—C21.385 (2)C5—H50.9300
C1—C61.393 (2)C6—H60.9300
C1—S11.7611 (17)N1—H1A0.90 (2)
C2—C31.379 (2)N1—H1B0.92 (3)
C2—H20.9300N1—H1C0.92 (3)
C3—C41.401 (2)N2—H2B0.8600
C3—N11.464 (2)N2—H2A0.8600
C4—N21.376 (2)O1—S11.4739 (14)
C4—C51.399 (2)O2—S11.4435 (14)
C5—C61.379 (2)O3—S11.4428 (14)
C2—C1—C6119.85 (15)C1—C6—H6120.0
C2—C1—S1119.92 (13)C3—N1—H1A109.1 (15)
C6—C1—S1120.23 (13)C3—N1—H1B111.8 (14)
C3—C2—C1119.66 (15)H1A—N1—H1B108 (2)
C3—C2—H2120.2C3—N1—H1C108.5 (14)
C1—C2—H2120.2H1A—N1—H1C108 (2)
C2—C3—C4121.88 (15)H1B—N1—H1C111 (2)
C2—C3—N1118.96 (15)C4—N2—H2B120.0
C4—C3—N1119.16 (15)C4—N2—H2A120.0
N2—C4—C5120.55 (16)H2B—N2—H2A120.0
N2—C4—C3122.25 (16)O3—S1—O2113.91 (10)
C5—C4—C3117.20 (15)O3—S1—O1110.55 (8)
C6—C5—C4121.48 (16)O2—S1—O1111.67 (9)
C6—C5—H5119.3O3—S1—C1108.61 (8)
C4—C5—H5119.3O2—S1—C1105.94 (8)
C5—C6—C1119.93 (16)O1—S1—C1105.68 (8)
C5—C6—H6120.0
C6—C1—C2—C30.9 (3)C4—C5—C6—C10.2 (3)
S1—C1—C2—C3−178.25 (13)C2—C1—C6—C5−1.0 (3)
C1—C2—C3—C40.0 (3)S1—C1—C6—C5178.15 (14)
C1—C2—C3—N1−179.58 (15)C2—C1—S1—O3106.55 (15)
C2—C3—C4—N2178.93 (17)C6—C1—S1—O3−72.59 (16)
N1—C3—C4—N2−1.5 (3)C2—C1—S1—O2−16.19 (17)
C2—C3—C4—C5−0.8 (3)C6—C1—S1—O2164.66 (15)
N1—C3—C4—C5178.80 (16)C2—C1—S1—O1−134.81 (14)
N2—C4—C5—C6−179.04 (18)C6—C1—S1—O146.04 (17)
C3—C4—C5—C60.7 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1B···O1i0.92 (3)1.86 (3)2.778 (2)178 (2)
N1—H1C···O1ii0.92 (3)1.89 (3)2.792 (2)165 (2)
N1—H1A···O2iii0.90 (2)1.88 (3)2.759 (2)165 (2)
N2—H2B···O3iv0.862.463.047 (2)126

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2799).

References

  • Bruker (2005). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Miranda, F. da S., Signori, A. M., Vicente, J., de Souza, B., Priebe, J. P., Szpoganicz, B., Sanches, N. G. & Neves, A. (2008). Tetrahedron, 64, 5410–5415.
  • Rubin-Preminger, J. M. & Bernstein, J. (2003). Helv. Chim. Acta, 86, 3037–3054.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography