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
CCDC reference: 610716
Key indicators
- Single-crystal X-ray study
- T = 297 K
- Mean (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
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+·2H2O | F(000) = 792 |
Mr = 377.37 | Dx = 1.528 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: P 2c -2n | Cell parameters from 25 reflections |
a = 7.1911 (6) Å | θ = 13.1–17.4° |
b = 12.1574 (12) Å | µ = 0.25 mm−1 |
c = 18.7595 (12) Å | T = 297 K |
V = 1640.1 (2) Å3 | Prism, pale brown |
Z = 4 | 0.44 × 0.30 × 0.15 mm |
Data collection top
Rigaku AFC-7R diffractometer | 1462 reflections with I > 2σ(I) |
Radiation source: Rigaku rotating anode | Rint = 0.022 |
Graphite monochromator | θmax = 27.5°, θmin = 3.3° |
ω–2θ scans | h = −4→9 |
Absorption correction: ψ scan (TEXSAN for Windows; Molecular Structure Corporation, 1999) | k = −7→15 |
Tmin = 0.899, Tmax = 0.964 | l = 0→24 |
2366 measured reflections | 3 standard reflections every 150 min |
1943 independent reflections | intensity decay: 0.9% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H 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 reflections | Δρmax = 0.28 e Å−3 |
226 parameters | Δρmin = −0.35 e Å−3 |
1 restraint | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute 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 | x | y | z | Uiso*/Ueq | |
S5 | 0.26072 (17) | 0.03932 (8) | 0.09999 (7) | 0.0246 (3) | |
O2 | 0.4155 (6) | 0.1969 (3) | 0.3909 (2) | 0.0387 (12) | |
O51 | 0.4202 (5) | 0.0683 (3) | 0.0557 (2) | 0.0365 (11) | |
O52 | 0.2211 (5) | −0.0773 (3) | 0.1015 (2) | 0.0390 (10) | |
O53 | 0.0952 (5) | 0.1033 (3) | 0.08118 (19) | 0.0377 (11) | |
O71 | 0.1935 (7) | −0.1155 (3) | 0.3624 (2) | 0.0391 (13) | |
O72 | 0.2579 (6) | 0.0196 (3) | 0.4383 (2) | 0.0421 (13) | |
C1 | 0.3012 (7) | 0.0515 (4) | 0.3147 (2) | 0.0247 (12) | |
C2 | 0.3862 (6) | 0.1547 (4) | 0.3251 (2) | 0.0263 (12) | |
C3 | 0.4422 (7) | 0.2172 (4) | 0.2672 (3) | 0.0313 (12) | |
C4 | 0.4081 (7) | 0.1802 (4) | 0.1987 (3) | 0.0287 (14) | |
C5 | 0.3185 (6) | 0.0797 (4) | 0.1879 (2) | 0.0240 (12) | |
C6 | 0.2689 (6) | 0.0147 (4) | 0.2451 (2) | 0.0233 (12) | |
C7 | 0.2495 (7) | −0.0150 (4) | 0.3770 (3) | 0.0272 (10)* | |
O31 | 0.8267 (6) | 0.0366 (3) | 0.33370 (19) | 0.0391 (11) | |
N11 | 0.7700 (7) | −0.0426 (4) | 0.08595 (19) | 0.0290 (12) | |
C11 | 0.7344 (6) | −0.0751 (4) | 0.1604 (2) | 0.0247 (12) | |
C21 | 0.7972 (7) | −0.0078 (4) | 0.2136 (3) | 0.0273 (12) | |
C31 | 0.7602 (7) | −0.0362 (4) | 0.2844 (3) | 0.0283 (14) | |
C32 | 0.7874 (9) | 0.0144 (6) | 0.4072 (3) | 0.044 (2) | |
C41 | 0.6626 (7) | −0.1318 (4) | 0.2994 (3) | 0.0320 (14) | |
C51 | 0.6010 (7) | −0.1974 (4) | 0.2436 (3) | 0.0350 (16) | |
C61 | 0.6372 (7) | −0.1698 (4) | 0.1741 (3) | 0.0313 (12) | |
O1W | 0.6532 (9) | 0.2563 (4) | 0.5198 (3) | 0.0537 (16) | |
O2W | 0.5686 (9) | 0.7293 (4) | 0.4729 (3) | 0.0647 (19) | |
H2 | 0.373 (11) | 0.154 (6) | 0.417 (4) | 0.05 (2)* | |
H3 | 0.503600 | 0.285400 | 0.274400 | 0.0380* | |
H4 | 0.445500 | 0.223600 | 0.159100 | 0.0340* | |
H6 | 0.213100 | −0.055000 | 0.237400 | 0.0280* | |
H71 | 0.185 (8) | −0.155 (5) | 0.400 (3) | 0.022 (15)* | |
H11A | 0.672 (11) | −0.015 (5) | 0.070 (4) | 0.043 (18)* | |
H11B | 0.784 (10) | −0.102 (7) | 0.062 (4) | 0.06 (2)* | |
H11C | 0.870 (11) | 0.004 (6) | 0.084 (4) | 0.06 (2)* | |
H21 | 0.865900 | 0.056800 | 0.202600 | 0.0340* | |
H23A | 0.863400 | 0.059500 | 0.436500 | 0.0530* | |
H23B | 0.660400 | 0.029100 | 0.416700 | 0.0530* | |
H23C | 0.813300 | −0.060900 | 0.417100 | 0.0530* | |
H41 | 0.636100 | −0.152200 | 0.347000 | 0.0380* | |
H51 | 0.533800 | −0.262600 | 0.253800 | 0.0420* | |
H61 | 0.595600 | −0.215400 | 0.136200 | 0.0380* | |
H11W | 0.573 (12) | 0.241 (8) | 0.482 (5) | 0.08 (2)* | |
H12W | 0.667 (12) | 0.195 (7) | 0.543 (5) | 0.07 (2)* | |
H21W | 0.516 (11) | 0.689 (7) | 0.508 (4) | 0.09 (2)* | |
H22W | 0.598 (11) | 0.790 (7) | 0.494 (4) | 0.06 (2)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S5 | 0.0312 (5) | 0.0262 (5) | 0.0165 (4) | 0.0007 (5) | −0.0015 (5) | 0.0012 (5) |
O2 | 0.051 (2) | 0.038 (2) | 0.027 (2) | −0.0052 (18) | −0.0057 (17) | −0.0096 (17) |
O51 | 0.0357 (19) | 0.047 (2) | 0.0267 (17) | 0.0000 (16) | 0.0057 (15) | 0.0044 (16) |
O52 | 0.064 (2) | 0.0269 (14) | 0.0262 (15) | −0.0080 (16) | −0.004 (2) | −0.0035 (18) |
O53 | 0.0351 (18) | 0.042 (2) | 0.036 (2) | 0.0061 (16) | −0.0072 (15) | 0.0041 (16) |
O71 | 0.064 (3) | 0.033 (2) | 0.0204 (18) | −0.0042 (19) | 0.0074 (16) | 0.0032 (15) |
O72 | 0.061 (3) | 0.044 (2) | 0.0212 (18) | −0.0065 (19) | −0.0016 (18) | −0.0016 (18) |
C1 | 0.025 (2) | 0.029 (2) | 0.020 (2) | 0.0023 (17) | −0.0017 (16) | −0.0003 (18) |
C2 | 0.029 (2) | 0.027 (2) | 0.023 (2) | 0.0036 (18) | −0.0044 (17) | −0.0054 (18) |
C3 | 0.032 (2) | 0.029 (2) | 0.033 (2) | −0.008 (2) | −0.006 (2) | −0.0055 (19) |
C4 | 0.036 (3) | 0.023 (2) | 0.027 (2) | −0.0025 (18) | 0.0011 (19) | 0.0015 (19) |
C5 | 0.026 (2) | 0.025 (2) | 0.021 (2) | 0.0014 (18) | −0.0034 (17) | −0.0034 (17) |
C6 | 0.025 (2) | 0.026 (2) | 0.019 (2) | 0.0004 (18) | −0.0021 (18) | −0.0015 (16) |
C7 | 0.031 (2) | 0.030 (2) | 0.020 (2) | 0.004 (2) | −0.0019 (19) | −0.0027 (19) |
O31 | 0.055 (2) | 0.041 (2) | 0.0213 (18) | −0.0048 (18) | 0.0022 (17) | −0.0026 (15) |
N11 | 0.034 (2) | 0.037 (2) | 0.016 (2) | 0.001 (2) | −0.0007 (17) | 0.0005 (16) |
C11 | 0.028 (2) | 0.028 (2) | 0.018 (2) | 0.0041 (18) | 0.0000 (17) | 0.0022 (17) |
C21 | 0.029 (2) | 0.030 (2) | 0.023 (2) | −0.0013 (18) | −0.0012 (18) | 0.0027 (19) |
C31 | 0.030 (2) | 0.030 (2) | 0.025 (3) | 0.004 (2) | −0.0003 (19) | −0.0007 (18) |
C32 | 0.048 (4) | 0.066 (4) | 0.017 (2) | 0.008 (3) | 0.001 (2) | −0.001 (2) |
C41 | 0.037 (3) | 0.032 (2) | 0.027 (2) | 0.002 (2) | 0.008 (2) | 0.007 (2) |
C51 | 0.031 (2) | 0.030 (3) | 0.044 (3) | 0.000 (2) | 0.004 (2) | 0.004 (2) |
C61 | 0.035 (2) | 0.029 (2) | 0.030 (2) | 0.003 (2) | 0.000 (2) | −0.0022 (19) |
O1W | 0.083 (4) | 0.039 (2) | 0.039 (2) | 0.002 (2) | 0.018 (3) | 0.000 (2) |
O2W | 0.104 (4) | 0.046 (3) | 0.044 (3) | −0.021 (3) | 0.035 (3) | −0.014 (2) |
Geometric parameters (Å, º) top
S5—O51 | 1.459 (4) | C1—C2 | 1.409 (7) |
S5—O52 | 1.446 (4) | C2—C3 | 1.385 (7) |
S5—O53 | 1.465 (4) | C3—C4 | 1.383 (8) |
S5—C5 | 1.770 (4) | C4—C5 | 1.396 (7) |
O2—C2 | 1.353 (5) | C5—C6 | 1.380 (6) |
O71—C7 | 1.315 (6) | C3—H3 | 0.9490 |
O72—C7 | 1.226 (7) | C4—H4 | 0.9500 |
O2—H2 | 0.78 (7) | C6—H6 | 0.9486 |
O71—H71 | 0.86 (6) | C11—C21 | 1.367 (7) |
O31—C31 | 1.367 (6) | C11—C61 | 1.371 (7) |
O31—C32 | 1.433 (7) | C21—C31 | 1.398 (8) |
O1W—H11W | 0.93 (9) | C31—C41 | 1.387 (7) |
O1W—H12W | 0.87 (9) | C41—C51 | 1.389 (8) |
O2W—H22W | 0.86 (9) | C51—C61 | 1.371 (8) |
O2W—H21W | 0.90 (8) | C21—H21 | 0.9505 |
N11—C11 | 1.474 (5) | C32—H23A | 0.9494 |
N11—H11A | 0.84 (8) | C32—H23B | 0.9475 |
N11—H11C | 0.92 (8) | C32—H23C | 0.9525 |
N11—H11B | 0.86 (8) | C41—H41 | 0.9461 |
C1—C7 | 1.469 (7) | C51—H51 | 0.9479 |
C1—C6 | 1.400 (6) | C61—H61 | 0.9499 |
| | | |
O51—S5—O52 | 113.7 (2) | O71—C7—O72 | 121.9 (5) |
O51—S5—O53 | 111.9 (2) | C4—C3—H3 | 119.92 |
O51—S5—C5 | 106.2 (2) | C2—C3—H3 | 120.19 |
O52—S5—O53 | 111.4 (2) | C3—C4—H4 | 119.71 |
O52—S5—C5 | 107.4 (2) | C5—C4—H4 | 120.21 |
O53—S5—C5 | 105.5 (2) | C1—C6—H6 | 119.85 |
C2—O2—H2 | 105 (6) | C5—C6—H6 | 120.17 |
C7—O71—H71 | 112 (4) | N11—C11—C61 | 119.4 (4) |
C31—O31—C32 | 117.4 (4) | C21—C11—C61 | 122.3 (4) |
H11W—O1W—H12W | 106 (8) | N11—C11—C21 | 118.3 (4) |
H21W—O2W—H22W | 103 (7) | C11—C21—C31 | 118.9 (4) |
C11—N11—H11B | 107 (5) | O31—C31—C21 | 114.6 (4) |
H11A—N11—H11B | 104 (7) | O31—C31—C41 | 125.6 (5) |
H11A—N11—H11C | 114 (7) | C21—C31—C41 | 119.7 (5) |
C11—N11—H11C | 110 (5) | C31—C41—C51 | 119.3 (5) |
H11B—N11—H11C | 114 (7) | C41—C51—C61 | 121.0 (5) |
C11—N11—H11A | 107 (5) | C11—C61—C51 | 118.7 (5) |
C2—C1—C7 | 119.3 (4) | C11—C21—H21 | 120.51 |
C2—C1—C6 | 119.1 (4) | C31—C21—H21 | 120.62 |
C6—C1—C7 | 121.6 (4) | O31—C32—H23B | 109.60 |
C1—C2—C3 | 120.4 (4) | O31—C32—H23A | 109.56 |
O2—C2—C1 | 122.1 (4) | H23A—C32—H23C | 109.24 |
O2—C2—C3 | 117.5 (4) | O31—C32—H23C | 109.27 |
C2—C3—C4 | 119.9 (4) | H23A—C32—H23B | 109.70 |
C3—C4—C5 | 120.1 (5) | H23B—C32—H23C | 109.46 |
C4—C5—C6 | 120.5 (4) | C51—C41—H41 | 119.78 |
S5—C5—C6 | 120.3 (4) | C31—C41—H41 | 120.88 |
S5—C5—C4 | 119.1 (4) | C41—C51—H51 | 119.39 |
C1—C6—C5 | 120.0 (4) | C61—C51—H51 | 119.56 |
O71—C7—C1 | 115.0 (5) | C51—C61—H61 | 120.60 |
O72—C7—C1 | 123.0 (4) | C11—C61—H61 | 120.68 |
| | | |
O51—S5—C5—C4 | 41.6 (4) | O2—C2—C3—C4 | −177.1 (4) |
O51—S5—C5—C6 | −140.9 (4) | C1—C2—C3—C4 | 2.5 (7) |
O52—S5—C5—C4 | 163.7 (4) | C2—C3—C4—C5 | −0.4 (7) |
O52—S5—C5—C6 | −18.9 (4) | C3—C4—C5—C6 | −2.2 (7) |
O53—S5—C5—C4 | −77.3 (4) | C3—C4—C5—S5 | 175.2 (4) |
O53—S5—C5—C6 | 100.1 (4) | S5—C5—C6—C1 | −174.7 (4) |
C32—O31—C31—C21 | 177.7 (5) | C4—C5—C6—C1 | 2.7 (7) |
C32—O31—C31—C41 | −2.1 (8) | N11—C11—C21—C31 | 178.4 (4) |
C6—C1—C2—O2 | 177.6 (4) | C61—C11—C21—C31 | −0.3 (7) |
C6—C1—C7—O72 | −172.1 (5) | C21—C11—C61—C51 | 0.4 (7) |
C6—C1—C7—O71 | 8.1 (7) | N11—C11—C61—C51 | −178.3 (4) |
C6—C1—C2—C3 | −2.0 (7) | C11—C21—C31—C41 | 0.5 (7) |
C7—C1—C2—C3 | 177.7 (4) | C11—C21—C31—O31 | −179.3 (4) |
C2—C1—C7—O72 | 8.2 (8) | O31—C31—C41—C51 | 179.1 (5) |
C2—C1—C7—O71 | −171.6 (5) | C21—C31—C41—C51 | −0.8 (7) |
C2—C1—C6—C5 | −0.6 (7) | C31—C41—C51—C61 | 0.8 (8) |
C7—C1—C6—C5 | 179.7 (5) | C41—C51—C61—C11 | −0.6 (8) |
C7—C1—C2—O2 | −2.7 (7) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O72 | 0.78 (7) | 1.88 (7) | 2.593 (5) | 153 (8) |
O71—H71···O2Wi | 0.86 (6) | 1.84 (6) | 2.649 (7) | 157 (6) |
N11—H11A···O51 | 0.84 (7) | 2.09 (8) | 2.910 (6) | 166 (7) |
N11—H11A···O72ii | 0.84 (7) | 2.52 (8) | 2.791 (5) | 100 (6) |
N11—H11B···O1Wiii | 0.86 (8) | 1.95 (8) | 2.797 (7) | 170 (5) |
N11—H11C···O53iv | 0.92 (8) | 2.02 (8) | 2.937 (6) | 178 (10) |
O1W—H11W···O2 | 0.93 (9) | 2.12 (9) | 3.048 (7) | 174 (9) |
O1W—H12W···O52v | 0.87 (9) | 1.98 (9) | 2.811 (6) | 161 (7) |
O2W—H21W···O53vi | 0.90 (8) | 1.90 (8) | 2.804 (7) | 180 (10) |
O2W—H22W···O51vii | 0.86 (9) | 2.08 (8) | 2.911 (6) | 161 (7) |
C6—H6···O52 | 0.95 | 2.56 | 2.937 (5) | 104 |
Symmetry codes: (i) x−1/2, −y+1/2, z; (ii) −x+1, −y, z−1/2; (iii) −x+3/2, y−1/2, z−1/2; (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. |