organic compounds
3-Amino-4-methoxybenzenesulfonic acid exists in the solid state in the zwitterionic form as 3-ammonio-4-methoxybenzenesulfonate, C7H9NO4S. The zwitterions are linked by the ammonium H atoms into a layer structure.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680500293X/is6043sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680500293X/is6043Isup2.hkl |
CCDC reference: 269790
Computing details top
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
3-Ammonio-4-methoxybenzenesulfonate top
Crystal data top
C7H9NO4S | Z = 2 |
Mr = 203.21 | F(000) = 212 |
Triclinic, P1 | Dx = 1.678 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.321 (2) Å | Cell parameters from 3869 reflections |
b = 8.234 (2) Å | θ = 3.1–27.5° |
c = 8.354 (2) Å | µ = 0.38 mm−1 |
α = 62.05 (3)° | T = 295 K |
β = 65.34 (3)° | Prism, colorless |
γ = 74.04 (3)° | 0.34 × 0.26 × 0.19 mm |
V = 402.3 (1) Å3 |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 1830 independent reflections |
Radiation source: fine-focus sealed tube | 1713 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.011 |
ω scans | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −9→8 |
Tmin = 0.810, Tmax = 0.931 | k = −10→10 |
3979 measured reflections | l = −10→10 |
Refinement top
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)] = 0.028 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.084 | All H-atom parameters refined |
S = 1.04 | w = 1/[σ2(Fo2) + (0.053P)2 + 0.1821P] where P = (Fo2 + 2Fc2)/3 |
1830 reflections | (Δ/σ)max = 0.001 |
154 parameters | Δρmax = 0.33 e Å−3 |
9 restraints | Δρmin = −0.38 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
S1 | 0.20715 (5) | 0.17966 (4) | 0.70736 (4) | 0.0182 (1) | |
O1 | 0.3589 (2) | 0.0521 (1) | 0.7911 (2) | 0.0259 (2) | |
O2 | 0.1115 (2) | 0.0881 (1) | 0.6530 (2) | 0.0252 (2) | |
O3 | 0.0620 (2) | 0.2766 (2) | 0.8221 (2) | 0.0293 (3) | |
O4 | 0.6393 (2) | 0.7397 (1) | −0.0404 (1) | 0.0241 (2) | |
N1 | 0.3040 (2) | 0.8525 (2) | 0.1882 (2) | 0.0201 (2) | |
C1 | 0.3461 (2) | 0.3464 (2) | 0.4875 (2) | 0.0185 (3) | |
C2 | 0.2715 (2) | 0.5314 (2) | 0.4307 (2) | 0.0185 (3) | |
C3 | 0.3757 (2) | 0.6567 (2) | 0.2520 (2) | 0.0178 (3) | |
C4 | 0.5540 (2) | 0.6018 (2) | 0.1294 (2) | 0.0186 (3) | |
C5 | 0.6265 (2) | 0.4157 (2) | 0.1873 (2) | 0.0218 (3) | |
C6 | 0.5224 (2) | 0.2889 (2) | 0.3667 (2) | 0.0220 (3) | |
C7 | 0.8295 (3) | 0.6943 (2) | −0.1674 (2) | 0.0306 (3) | |
H1n1 | 0.313 (3) | 0.904 (3) | 0.069 (2) | 0.042 (6)* | |
H1n2 | 0.179 (2) | 0.872 (3) | 0.249 (3) | 0.034 (5)* | |
H1n3 | 0.370 (3) | 0.910 (3) | 0.206 (3) | 0.033 (5)* | |
H2 | 0.152 (2) | 0.574 (2) | 0.510 (2) | 0.029 (5)* | |
H5 | 0.744 (2) | 0.373 (3) | 0.106 (2) | 0.033 (5)* | |
H6 | 0.575 (3) | 0.163 (1) | 0.404 (2) | 0.027 (4)* | |
H71 | 0.936 (3) | 0.651 (3) | −0.117 (3) | 0.052 (6)* | |
H72 | 0.853 (3) | 0.800 (2) | −0.286 (2) | 0.051 (6)* | |
H73 | 0.828 (3) | 0.597 (2) | −0.198 (3) | 0.046 (6)* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0171 (2) | 0.0166 (2) | 0.0171 (2) | −0.0018 (1) | −0.0062 (1) | −0.0035 (1) |
O1 | 0.0238 (5) | 0.0233 (5) | 0.0243 (5) | −0.0021 (4) | −0.0128 (4) | −0.0007 (4) |
O2 | 0.0216 (5) | 0.0266 (5) | 0.0277 (5) | −0.0069 (4) | −0.0078 (4) | −0.0093 (4) |
O3 | 0.0292 (6) | 0.0277 (5) | 0.0241 (5) | −0.0007 (4) | −0.0032 (4) | −0.0113 (4) |
O4 | 0.0213 (5) | 0.0215 (5) | 0.0186 (5) | −0.0020 (4) | −0.0020 (4) | −0.0038 (4) |
N1 | 0.0170 (6) | 0.0163 (5) | 0.0213 (6) | −0.0017 (4) | −0.0056 (5) | −0.0039 (4) |
C1 | 0.0178 (6) | 0.0174 (6) | 0.0179 (6) | −0.0033 (5) | −0.0067 (5) | −0.0040 (5) |
C2 | 0.0164 (6) | 0.0194 (6) | 0.0183 (6) | −0.0014 (5) | −0.0059 (5) | −0.0065 (5) |
C3 | 0.0169 (6) | 0.0151 (6) | 0.0202 (6) | −0.0009 (5) | −0.0084 (5) | −0.0049 (5) |
C4 | 0.0169 (6) | 0.0204 (6) | 0.0177 (6) | −0.0030 (5) | −0.0067 (5) | −0.0057 (5) |
C5 | 0.0171 (6) | 0.0227 (7) | 0.0228 (7) | 0.0003 (5) | −0.0047 (5) | −0.0101 (5) |
C6 | 0.0210 (7) | 0.0167 (6) | 0.0251 (7) | 0.0003 (5) | −0.0082 (5) | −0.0069 (5) |
C7 | 0.0248 (7) | 0.0343 (8) | 0.0226 (7) | −0.0032 (6) | 0.0002 (6) | −0.0107 (6) |
Geometric parameters (Å, º) top
S1—O1 | 1.465 (1) | C4—C5 | 1.391 (2) |
S1—O2 | 1.464 (1) | C5—C6 | 1.391 (2) |
S1—O3 | 1.445 (1) | N1—H1n1 | 0.86 (1) |
S1—C1 | 1.771 (2) | N1—H1n2 | 0.86 (1) |
O4—C4 | 1.354 (2) | N1—H1n3 | 0.86 (1) |
O4—C7 | 1.434 (2) | C2—H2 | 0.95 (1) |
N1—C3 | 1.457 (2) | C5—H5 | 0.95 (1) |
C1—C2 | 1.387 (2) | C6—H6 | 0.95 (1) |
C1—C6 | 1.390 (2) | C7—H71 | 0.95 (1) |
C2—C3 | 1.384 (2) | C7—H72 | 0.95 (1) |
C3—C4 | 1.397 (2) | C7—H73 | 0.95 (1) |
O1—S1—O2 | 111.1 (1) | C3—N1—H1n1 | 113 (2) |
O1—S1—O3 | 114.4 (1) | C3—N1—H1n2 | 112 (1) |
O2—S1—O3 | 112.6 (1) | H1n1—N1—H1n2 | 104 (2) |
C1—S1—O1 | 105.0 (1) | C3—N1—H1n3 | 110 (1) |
C1—S1—O2 | 105.4 (1) | H1n1—N1—H1n3 | 109 (2) |
C1—S1—O3 | 107.6 (1) | H1n2—N1—H1n3 | 108 (2) |
C4—O4—C7 | 117.8 (1) | C3—C2—H2 | 119 (1) |
C2—C1—C6 | 120.4 (1) | C1—C2—H2 | 122 (1) |
C2—C1—S1 | 120.0 (1) | C4—C5—H5 | 121 (1) |
C6—C1—S1 | 119.5 (1) | C6—C5—H5 | 119 (1) |
C1—C2—C3 | 118.7 (1) | C5—C6—H6 | 118 (1) |
C2—C3—C4 | 121.7 (1) | C1—C6—H6 | 121 (1) |
C2—C3—N1 | 120.4 (1) | O4—C7—H71 | 114 (2) |
C4—C3—N1 | 117.9 (1) | O4—C7—H72 | 106 (1) |
O4—C4—C5 | 125.9 (1) | H71—C7—H72 | 115 (2) |
O4—C4—C3 | 115.1 (1) | O4—C7—H73 | 114 (1) |
C3—C4—C5 | 119.1 (1) | H71—C7—H73 | 103 (2) |
C4—C5—C6 | 119.5 (1) | H72—C7—H73 | 105 (2) |
C1—C6—C6 | 120.6 (1) | ||
O3—S1—C1—C2 | −17.6 (1) | C7—O4—C4—C3 | 176.1 (1) |
O2—S1—C1—C2 | 102.8 (1) | C2—C3—C4—O4 | −179.8 (1) |
O1—S1—C1—C2 | −139.8 (1) | N1—C3—C4—O4 | −1.3 (2) |
O3—S1—C1—C6 | 166.9 (1) | C2—C3—C4—C5 | 1.1 (2) |
O2—S1—C1—C6 | −72.7 (1) | N1—C3—C4—C5 | 179.6 (1) |
O1—S1—C1—C6 | 44.7 (1) | O4—C4—C5—C6 | −180.0 (1) |
C6—C1—C2—C3 | 0.1 (2) | C3—C4—C5—C6 | −1.0 (2) |
S1—C1—C2—C3 | −175.3 (1) | C4—C5—C6—C1 | 0.5 (2) |
C1—C2—C3—C4 | −0.7 (2) | C2—C1—C6—C5 | 0.0 (2) |
C1—C2—C3—N1 | −179.1 (1) | S1—C1—C6—C5 | 175.5 (1) |
C7—O4—C4—C5 | −4.9 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1n1···O1i | 0.86 (1) | 1.98 (1) | 2.829 (2) | 171 (2) |
N1—H1n2···O2ii | 0.86 (1) | 1.93 (1) | 2.770 (2) | 169 (2) |
N1—H1n3···O1iii | 0.86 (1) | 2.10 (1) | 2.878 (2) | 151 (2) |
Symmetry codes: (i) x, y+1, z−1; (ii) −x, −y+1, −z+1; (iii) −x+1, −y+1, −z+1. |