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The 1:1 proton-transfer compound of m-anisidine with 5-sulfosalicylic acid, 3-methoxy­anilinium 3-carb­oxy-4-hydroxy­benzene­sulfonate dihydrate, C7H10NO+·C7H5O6S-·2H2O, is a three-dimensional framework structure built from hydrogen-bonding inter­actions involving the aminium group of the cation, the two water mol­ecules of solvation and the sulfonate, carboxyl­ate and phenolic substituent groups of the anion.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806017090/bt2078sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806017090/bt2078Isup2.hkl
Contains datablock I

CCDC reference: 610716

Key indicators

  • Single-crystal X-ray study
  • T = 297 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.037
  • wR factor = 0.129
  • Data-to-parameter ratio = 8.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
Alert level G ABSTY01_ALERT_1_G Extra text has been found in the _exptl_absorpt_correction_type field, which should be only a single keyword. A literature citation should be included in the _exptl_absorpt_process_details field. REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 27.49 From the CIF: _reflns_number_total 1943 Count of symmetry unique reflns 1944 Completeness (_total/calc) 99.95% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: MSC/AFC Diffractmeter Control Software (Molecular Structure Corporation, 1999); cell refinement: MSC/AFC Diffractmeter Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

3-methoxyanilinium 3-carboxy-4-hydroxybenzenesulfonate dihydrate top
Crystal data top
C7H5O6S·C7H10NO+·2H2OF(000) = 792
Mr = 377.37Dx = 1.528 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2c -2nCell parameters from 25 reflections
a = 7.1911 (6) Åθ = 13.1–17.4°
b = 12.1574 (12) ŵ = 0.25 mm1
c = 18.7595 (12) ÅT = 297 K
V = 1640.1 (2) Å3Prism, pale brown
Z = 40.44 × 0.30 × 0.15 mm
Data collection top
Rigaku AFC-7R
diffractometer
1462 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anodeRint = 0.022
Graphite monochromatorθmax = 27.5°, θmin = 3.3°
ω–2θ scansh = 49
Absorption correction: ψ scan
(TEXSAN for Windows; Molecular Structure Corporation, 1999)
k = 715
Tmin = 0.899, Tmax = 0.964l = 024
2366 measured reflections3 standard reflections every 150 min
1943 independent reflections intensity decay: 0.9%
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)] = 0.037H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.129 w = 1/[σ2(Fo2) + (0.1P)2 + 2.5948P]
where P = (Fo2 + 2Fc2)/3
S = 0.84(Δ/σ)max = 0.002
1943 reflectionsΔρmax = 0.28 e Å3
226 parametersΔρmin = 0.35 e Å3
1 restraintAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.13 (14)
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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) top
xyzUiso*/Ueq
S50.26072 (17)0.03932 (8)0.09999 (7)0.0246 (3)
O20.4155 (6)0.1969 (3)0.3909 (2)0.0387 (12)
O510.4202 (5)0.0683 (3)0.0557 (2)0.0365 (11)
O520.2211 (5)0.0773 (3)0.1015 (2)0.0390 (10)
O530.0952 (5)0.1033 (3)0.08118 (19)0.0377 (11)
O710.1935 (7)0.1155 (3)0.3624 (2)0.0391 (13)
O720.2579 (6)0.0196 (3)0.4383 (2)0.0421 (13)
C10.3012 (7)0.0515 (4)0.3147 (2)0.0247 (12)
C20.3862 (6)0.1547 (4)0.3251 (2)0.0263 (12)
C30.4422 (7)0.2172 (4)0.2672 (3)0.0313 (12)
C40.4081 (7)0.1802 (4)0.1987 (3)0.0287 (14)
C50.3185 (6)0.0797 (4)0.1879 (2)0.0240 (12)
C60.2689 (6)0.0147 (4)0.2451 (2)0.0233 (12)
C70.2495 (7)0.0150 (4)0.3770 (3)0.0272 (10)*
O310.8267 (6)0.0366 (3)0.33370 (19)0.0391 (11)
N110.7700 (7)0.0426 (4)0.08595 (19)0.0290 (12)
C110.7344 (6)0.0751 (4)0.1604 (2)0.0247 (12)
C210.7972 (7)0.0078 (4)0.2136 (3)0.0273 (12)
C310.7602 (7)0.0362 (4)0.2844 (3)0.0283 (14)
C320.7874 (9)0.0144 (6)0.4072 (3)0.044 (2)
C410.6626 (7)0.1318 (4)0.2994 (3)0.0320 (14)
C510.6010 (7)0.1974 (4)0.2436 (3)0.0350 (16)
C610.6372 (7)0.1698 (4)0.1741 (3)0.0313 (12)
O1W0.6532 (9)0.2563 (4)0.5198 (3)0.0537 (16)
O2W0.5686 (9)0.7293 (4)0.4729 (3)0.0647 (19)
H20.373 (11)0.154 (6)0.417 (4)0.05 (2)*
H30.5036000.2854000.2744000.0380*
H40.4455000.2236000.1591000.0340*
H60.2131000.0550000.2374000.0280*
H710.185 (8)0.155 (5)0.400 (3)0.022 (15)*
H11A0.672 (11)0.015 (5)0.070 (4)0.043 (18)*
H11B0.784 (10)0.102 (7)0.062 (4)0.06 (2)*
H11C0.870 (11)0.004 (6)0.084 (4)0.06 (2)*
H210.8659000.0568000.2026000.0340*
H23A0.8634000.0595000.4365000.0530*
H23B0.6604000.0291000.4167000.0530*
H23C0.8133000.0609000.4171000.0530*
H410.6361000.1522000.3470000.0380*
H510.5338000.2626000.2538000.0420*
H610.5956000.2154000.1362000.0380*
H11W0.573 (12)0.241 (8)0.482 (5)0.08 (2)*
H12W0.667 (12)0.195 (7)0.543 (5)0.07 (2)*
H21W0.516 (11)0.689 (7)0.508 (4)0.09 (2)*
H22W0.598 (11)0.790 (7)0.494 (4)0.06 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S50.0312 (5)0.0262 (5)0.0165 (4)0.0007 (5)0.0015 (5)0.0012 (5)
O20.051 (2)0.038 (2)0.027 (2)0.0052 (18)0.0057 (17)0.0096 (17)
O510.0357 (19)0.047 (2)0.0267 (17)0.0000 (16)0.0057 (15)0.0044 (16)
O520.064 (2)0.0269 (14)0.0262 (15)0.0080 (16)0.004 (2)0.0035 (18)
O530.0351 (18)0.042 (2)0.036 (2)0.0061 (16)0.0072 (15)0.0041 (16)
O710.064 (3)0.033 (2)0.0204 (18)0.0042 (19)0.0074 (16)0.0032 (15)
O720.061 (3)0.044 (2)0.0212 (18)0.0065 (19)0.0016 (18)0.0016 (18)
C10.025 (2)0.029 (2)0.020 (2)0.0023 (17)0.0017 (16)0.0003 (18)
C20.029 (2)0.027 (2)0.023 (2)0.0036 (18)0.0044 (17)0.0054 (18)
C30.032 (2)0.029 (2)0.033 (2)0.008 (2)0.006 (2)0.0055 (19)
C40.036 (3)0.023 (2)0.027 (2)0.0025 (18)0.0011 (19)0.0015 (19)
C50.026 (2)0.025 (2)0.021 (2)0.0014 (18)0.0034 (17)0.0034 (17)
C60.025 (2)0.026 (2)0.019 (2)0.0004 (18)0.0021 (18)0.0015 (16)
C70.031 (2)0.030 (2)0.020 (2)0.004 (2)0.0019 (19)0.0027 (19)
O310.055 (2)0.041 (2)0.0213 (18)0.0048 (18)0.0022 (17)0.0026 (15)
N110.034 (2)0.037 (2)0.016 (2)0.001 (2)0.0007 (17)0.0005 (16)
C110.028 (2)0.028 (2)0.018 (2)0.0041 (18)0.0000 (17)0.0022 (17)
C210.029 (2)0.030 (2)0.023 (2)0.0013 (18)0.0012 (18)0.0027 (19)
C310.030 (2)0.030 (2)0.025 (3)0.004 (2)0.0003 (19)0.0007 (18)
C320.048 (4)0.066 (4)0.017 (2)0.008 (3)0.001 (2)0.001 (2)
C410.037 (3)0.032 (2)0.027 (2)0.002 (2)0.008 (2)0.007 (2)
C510.031 (2)0.030 (3)0.044 (3)0.000 (2)0.004 (2)0.004 (2)
C610.035 (2)0.029 (2)0.030 (2)0.003 (2)0.000 (2)0.0022 (19)
O1W0.083 (4)0.039 (2)0.039 (2)0.002 (2)0.018 (3)0.000 (2)
O2W0.104 (4)0.046 (3)0.044 (3)0.021 (3)0.035 (3)0.014 (2)
Geometric parameters (Å, º) top
S5—O511.459 (4)C1—C21.409 (7)
S5—O521.446 (4)C2—C31.385 (7)
S5—O531.465 (4)C3—C41.383 (8)
S5—C51.770 (4)C4—C51.396 (7)
O2—C21.353 (5)C5—C61.380 (6)
O71—C71.315 (6)C3—H30.9490
O72—C71.226 (7)C4—H40.9500
O2—H20.78 (7)C6—H60.9486
O71—H710.86 (6)C11—C211.367 (7)
O31—C311.367 (6)C11—C611.371 (7)
O31—C321.433 (7)C21—C311.398 (8)
O1W—H11W0.93 (9)C31—C411.387 (7)
O1W—H12W0.87 (9)C41—C511.389 (8)
O2W—H22W0.86 (9)C51—C611.371 (8)
O2W—H21W0.90 (8)C21—H210.9505
N11—C111.474 (5)C32—H23A0.9494
N11—H11A0.84 (8)C32—H23B0.9475
N11—H11C0.92 (8)C32—H23C0.9525
N11—H11B0.86 (8)C41—H410.9461
C1—C71.469 (7)C51—H510.9479
C1—C61.400 (6)C61—H610.9499
O51—S5—O52113.7 (2)O71—C7—O72121.9 (5)
O51—S5—O53111.9 (2)C4—C3—H3119.92
O51—S5—C5106.2 (2)C2—C3—H3120.19
O52—S5—O53111.4 (2)C3—C4—H4119.71
O52—S5—C5107.4 (2)C5—C4—H4120.21
O53—S5—C5105.5 (2)C1—C6—H6119.85
C2—O2—H2105 (6)C5—C6—H6120.17
C7—O71—H71112 (4)N11—C11—C61119.4 (4)
C31—O31—C32117.4 (4)C21—C11—C61122.3 (4)
H11W—O1W—H12W106 (8)N11—C11—C21118.3 (4)
H21W—O2W—H22W103 (7)C11—C21—C31118.9 (4)
C11—N11—H11B107 (5)O31—C31—C21114.6 (4)
H11A—N11—H11B104 (7)O31—C31—C41125.6 (5)
H11A—N11—H11C114 (7)C21—C31—C41119.7 (5)
C11—N11—H11C110 (5)C31—C41—C51119.3 (5)
H11B—N11—H11C114 (7)C41—C51—C61121.0 (5)
C11—N11—H11A107 (5)C11—C61—C51118.7 (5)
C2—C1—C7119.3 (4)C11—C21—H21120.51
C2—C1—C6119.1 (4)C31—C21—H21120.62
C6—C1—C7121.6 (4)O31—C32—H23B109.60
C1—C2—C3120.4 (4)O31—C32—H23A109.56
O2—C2—C1122.1 (4)H23A—C32—H23C109.24
O2—C2—C3117.5 (4)O31—C32—H23C109.27
C2—C3—C4119.9 (4)H23A—C32—H23B109.70
C3—C4—C5120.1 (5)H23B—C32—H23C109.46
C4—C5—C6120.5 (4)C51—C41—H41119.78
S5—C5—C6120.3 (4)C31—C41—H41120.88
S5—C5—C4119.1 (4)C41—C51—H51119.39
C1—C6—C5120.0 (4)C61—C51—H51119.56
O71—C7—C1115.0 (5)C51—C61—H61120.60
O72—C7—C1123.0 (4)C11—C61—H61120.68
O51—S5—C5—C441.6 (4)O2—C2—C3—C4177.1 (4)
O51—S5—C5—C6140.9 (4)C1—C2—C3—C42.5 (7)
O52—S5—C5—C4163.7 (4)C2—C3—C4—C50.4 (7)
O52—S5—C5—C618.9 (4)C3—C4—C5—C62.2 (7)
O53—S5—C5—C477.3 (4)C3—C4—C5—S5175.2 (4)
O53—S5—C5—C6100.1 (4)S5—C5—C6—C1174.7 (4)
C32—O31—C31—C21177.7 (5)C4—C5—C6—C12.7 (7)
C32—O31—C31—C412.1 (8)N11—C11—C21—C31178.4 (4)
C6—C1—C2—O2177.6 (4)C61—C11—C21—C310.3 (7)
C6—C1—C7—O72172.1 (5)C21—C11—C61—C510.4 (7)
C6—C1—C7—O718.1 (7)N11—C11—C61—C51178.3 (4)
C6—C1—C2—C32.0 (7)C11—C21—C31—C410.5 (7)
C7—C1—C2—C3177.7 (4)C11—C21—C31—O31179.3 (4)
C2—C1—C7—O728.2 (8)O31—C31—C41—C51179.1 (5)
C2—C1—C7—O71171.6 (5)C21—C31—C41—C510.8 (7)
C2—C1—C6—C50.6 (7)C31—C41—C51—C610.8 (8)
C7—C1—C6—C5179.7 (5)C41—C51—C61—C110.6 (8)
C7—C1—C2—O22.7 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O720.78 (7)1.88 (7)2.593 (5)153 (8)
O71—H71···O2Wi0.86 (6)1.84 (6)2.649 (7)157 (6)
N11—H11A···O510.84 (7)2.09 (8)2.910 (6)166 (7)
N11—H11A···O72ii0.84 (7)2.52 (8)2.791 (5)100 (6)
N11—H11B···O1Wiii0.86 (8)1.95 (8)2.797 (7)170 (5)
N11—H11C···O53iv0.92 (8)2.02 (8)2.937 (6)178 (10)
O1W—H11W···O20.93 (9)2.12 (9)3.048 (7)174 (9)
O1W—H12W···O52v0.87 (9)1.98 (9)2.811 (6)161 (7)
O2W—H21W···O53vi0.90 (8)1.90 (8)2.804 (7)180 (10)
O2W—H22W···O51vii0.86 (9)2.08 (8)2.911 (6)161 (7)
C6—H6···O520.952.562.937 (5)104
Symmetry codes: (i) x1/2, y+1/2, z; (ii) x+1, y, z1/2; (iii) x+3/2, y1/2, z1/2; (iv) x+1, y, z; (v) x+1, y, z+1/2; (vi) x+1/2, y+1/2, z+1/2; (vii) x+1, y+1, z+1/2.
 

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