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The crystal structure of the anhydrous 1:1 proton-transfer compound of 5-sulfosalicylic acid (3-carboxy-4-hydroxy­benzene­sulfonic acid) with 4-amino­benzoic acid, viz. 4-carboxy­anilinium 3-carboxy-4-hydroxy­benzene­sulfonate, C7H8NO2+·C7H5O6S, displays a hydrogen-bonded polymeric network structure involving primarily all aminium H-atom donors and sulfonate O-atom acceptors, and is propagated through homomolecular cyclic tail-to-tail interactions between the carboxylic acid substituent groups of both cation and anion species. In addition, there are some cation–anion π–π stacking associations.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805000152/bt6575sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805000152/bt6575Isup2.hkl
Contains datablock I

CCDC reference: 263689

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.040
  • wR factor = 0.117
  • Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for O711 - C71 .. 12.97 su PLAT230_ALERT_2_B Hirshfeld Test Diff for C11 - C61 .. 10.40 su PLAT230_ALERT_2_B Hirshfeld Test Diff for C41 - C51 .. 15.58 su
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for S5
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

4-carboxyanilinium 3-carboxy-4-hydroxybenzenesulfonate top
Crystal data top
C7H8NO2+·C7H5O6SF(000) = 1472
Mr = 355.31Dx = 1.591 Mg m3
Monoclinic, C2/cMelting point: 520.2–522.0 (decomposition) K
Hall symbol: -C 2ycMo Kα radiation, λ = 0.71073 Å
a = 32.264 (3) ÅCell parameters from 5543 reflections
b = 7.6517 (7) Åθ = 2.2–27.5°
c = 12.0672 (11) ŵ = 0.26 mm1
β = 95.242 (2)°T = 295 K
V = 2966.6 (5) Å3Cut block, pale brown
Z = 80.40 × 0.30 × 0.30 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
3011 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.058
Graphite monochromatorθmax = 27.5°, θmin = 2.5°
φ and ω scansh = 3241
8997 measured reflectionsk = 99
3361 independent reflectionsl = 1315
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0727P)2 + 1.1096P]
where P = (Fo2 + 2Fc2)/3
3361 reflections(Δ/σ)max = 0.001
241 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.49 e Å3
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
S50.286144 (10)1.04900 (4)0.36352 (3)0.0278 (1)
O20.44023 (4)0.74973 (18)0.21549 (10)0.0446 (4)
O510.29822 (4)1.18682 (16)0.44260 (11)0.0473 (4)
O520.26749 (4)0.90349 (16)0.41780 (11)0.0481 (4)
O530.26144 (4)1.1087 (2)0.26601 (11)0.0607 (5)
O710.48044 (3)0.90583 (18)0.38494 (10)0.0450 (4)
O720.44446 (4)1.05993 (19)0.50015 (11)0.0520 (5)
C10.40719 (4)0.92840 (19)0.34718 (11)0.0288 (4)
C20.40597 (5)0.82465 (19)0.25054 (12)0.0313 (4)
C30.36806 (5)0.7956 (2)0.18831 (12)0.0354 (4)
C40.33189 (5)0.8656 (2)0.22140 (12)0.0323 (4)
C50.33285 (4)0.96546 (17)0.31868 (11)0.0266 (4)
C60.37011 (4)0.99681 (19)0.38061 (11)0.0283 (4)
C70.44717 (5)0.9632 (2)0.41168 (12)0.0345 (4)
O7110.44997 (4)0.6931 (2)0.76322 (11)0.0545 (4)
O7210.48067 (4)0.6443 (2)0.60826 (11)0.0598 (5)
N410.28955 (4)0.53986 (18)0.42905 (12)0.0326 (4)
C110.40746 (4)0.6362 (2)0.59709 (12)0.0328 (4)
C210.40444 (5)0.5516 (2)0.49460 (13)0.0352 (4)
C310.36569 (5)0.5224 (2)0.43884 (12)0.0335 (4)
C410.33058 (4)0.57955 (17)0.48501 (11)0.0283 (4)
C510.33299 (5)0.6678 (2)0.58549 (13)0.0346 (4)
C610.37182 (5)0.6950 (2)0.64159 (13)0.0361 (4)
C710.44815 (5)0.6608 (2)0.66330 (14)0.0389 (5)
H20.4589 (8)0.773 (3)0.259 (2)0.063 (7)*
H30.3672000.7284000.1239000.0430*
H40.3068000.8464000.1790000.0390*
H60.3706001.0638000.4450000.0340*
H720.4665 (9)1.072 (3)0.530 (2)0.070 (8)*
H210.4284000.5149000.4638000.0420*
H310.3633000.4646000.3708000.0400*
H41A0.2706 (7)0.564 (3)0.4700 (19)0.050 (6)*
H41B0.2838 (8)0.592 (4)0.366 (2)0.073 (8)*
H41C0.2878 (7)0.420 (3)0.4147 (18)0.058 (6)*
H510.3091000.7080000.6147000.0420*
H610.3740000.7530000.7096000.0430*
H7210.5061 (11)0.652 (4)0.659 (3)0.112 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S50.0243 (2)0.0266 (2)0.0314 (2)0.0019 (1)0.0040 (1)0.0000 (1)
O20.0341 (6)0.0599 (8)0.0398 (6)0.0057 (5)0.0036 (5)0.0134 (5)
O510.0396 (6)0.0375 (6)0.0634 (8)0.0023 (5)0.0033 (5)0.0201 (5)
O520.0428 (7)0.0337 (6)0.0711 (8)0.0002 (5)0.0227 (6)0.0022 (5)
O530.0478 (8)0.0881 (10)0.0430 (7)0.0271 (7)0.0132 (6)0.0071 (7)
O710.0259 (5)0.0666 (8)0.0415 (6)0.0038 (5)0.0030 (5)0.0112 (6)
O720.0284 (6)0.0808 (10)0.0448 (7)0.0029 (6)0.0082 (5)0.0268 (6)
C10.0263 (7)0.0335 (7)0.0260 (7)0.0019 (5)0.0014 (5)0.0013 (5)
C20.0315 (7)0.0342 (7)0.0283 (7)0.0002 (6)0.0034 (5)0.0009 (5)
C30.0374 (8)0.0403 (8)0.0278 (7)0.0032 (6)0.0012 (6)0.0079 (6)
C40.0308 (7)0.0353 (7)0.0293 (7)0.0039 (6)0.0054 (5)0.0023 (5)
C50.0251 (6)0.0278 (7)0.0266 (6)0.0006 (5)0.0001 (5)0.0022 (5)
C60.0277 (7)0.0321 (7)0.0244 (6)0.0018 (5)0.0008 (5)0.0008 (5)
C70.0276 (7)0.0447 (9)0.0305 (7)0.0013 (6)0.0012 (6)0.0014 (6)
O7110.0363 (6)0.0782 (9)0.0462 (7)0.0100 (6)0.0110 (5)0.0186 (6)
O7210.0300 (6)0.1024 (12)0.0461 (7)0.0077 (7)0.0016 (5)0.0036 (7)
N410.0296 (7)0.0325 (7)0.0343 (7)0.0011 (5)0.0046 (5)0.0003 (5)
C110.0298 (7)0.0335 (7)0.0341 (7)0.0020 (6)0.0028 (6)0.0019 (6)
C210.0301 (7)0.0423 (8)0.0335 (8)0.0010 (6)0.0047 (6)0.0004 (6)
C310.0358 (8)0.0365 (8)0.0281 (7)0.0007 (6)0.0026 (6)0.0021 (5)
C410.0290 (7)0.0251 (6)0.0298 (7)0.0003 (5)0.0033 (5)0.0044 (5)
C510.0291 (7)0.0369 (8)0.0371 (7)0.0059 (6)0.0002 (6)0.0040 (6)
C610.0361 (8)0.0379 (8)0.0332 (7)0.0021 (6)0.0033 (6)0.0070 (6)
C710.0320 (8)0.0415 (8)0.0421 (8)0.0005 (6)0.0033 (6)0.0016 (6)
Geometric parameters (Å, º) top
S5—O511.4514 (13)C2—C31.393 (2)
S5—O521.4502 (13)C3—C41.376 (2)
S5—O531.4343 (14)C4—C51.399 (2)
S5—C51.7667 (14)C5—C61.3773 (19)
O2—C21.347 (2)C3—H30.9302
O71—C71.2298 (19)C4—H40.9290
O72—C71.309 (2)C6—H60.9298
O2—H20.78 (2)C11—C211.391 (2)
O72—H720.77 (3)C11—C611.388 (2)
O711—C711.227 (2)C11—C711.485 (2)
O721—C711.298 (2)C21—C311.383 (2)
O721—H7210.98 (4)C31—C411.378 (2)
N41—C411.4620 (19)C41—C511.384 (2)
N41—H41C0.93 (2)C51—C611.384 (2)
N41—H41B0.86 (3)C21—H210.9312
N41—H41A0.84 (2)C31—H310.9296
C1—C71.469 (2)C51—H510.9288
C1—C21.408 (2)C61—H610.9300
C1—C61.3986 (19)
O51—S5—O52111.00 (8)O71—C7—O72122.75 (15)
O51—S5—O53113.81 (8)C2—C3—H3119.75
O51—S5—C5106.20 (7)C4—C3—H3119.75
O52—S5—O53113.12 (8)C3—C4—H4119.87
O52—S5—C5105.15 (7)C5—C4—H4120.00
O53—S5—C5106.83 (7)C1—C6—H6119.85
C2—O2—H2107.2 (18)C5—C6—H6119.79
C7—O72—H72108.7 (18)C21—C11—C61120.10 (13)
C71—O721—H721110 (2)C21—C11—C71121.59 (13)
H41A—N41—H41C107 (2)C61—C11—C71118.28 (14)
H41B—N41—H41C107 (2)C11—C21—C31119.63 (14)
H41A—N41—H41B108 (2)C21—C31—C41119.47 (14)
C41—N41—H41A111.0 (16)N41—C41—C31119.36 (12)
C41—N41—H41B115.0 (18)N41—C41—C51118.82 (13)
C41—N41—H41C109.1 (14)C31—C41—C51121.77 (13)
C6—C1—C7120.81 (12)C41—C51—C61118.54 (14)
C2—C1—C7119.85 (13)C11—C61—C51120.46 (14)
C2—C1—C6119.33 (13)O711—C71—O721123.64 (16)
O2—C2—C3117.90 (13)O711—C71—C11120.98 (15)
O2—C2—C1122.56 (14)O721—C71—C11115.37 (14)
C1—C2—C3119.53 (14)C11—C21—H21120.12
C2—C3—C4120.50 (14)C31—C21—H21120.25
C3—C4—C5120.12 (14)C21—C31—H31120.33
C4—C5—C6120.12 (13)C41—C31—H31120.20
S5—C5—C6119.83 (10)C41—C51—H51120.80
S5—C5—C4120.04 (11)C61—C51—H51120.66
C1—C6—C5120.36 (12)C11—C61—H61119.84
O72—C7—C1114.46 (14)C51—C61—H61119.70
O71—C7—C1122.79 (13)
O51—S5—C5—C4162.57 (12)C3—C4—C5—C61.2 (2)
O51—S5—C5—C618.36 (13)C3—C4—C5—S5177.86 (11)
O52—S5—C5—C479.70 (13)C4—C5—C6—C10.4 (2)
O52—S5—C5—C699.37 (12)S5—C5—C6—C1178.70 (11)
O53—S5—C5—C440.76 (14)C21—C11—C61—C511.0 (2)
O53—S5—C5—C6140.17 (12)C61—C11—C21—C311.7 (2)
C7—C1—C2—O22.1 (2)C71—C11—C61—C51176.96 (14)
C2—C1—C7—O710.3 (2)C21—C11—C71—O711161.05 (16)
C2—C1—C7—O72179.51 (14)C21—C11—C71—O72118.4 (2)
C6—C1—C7—O71179.83 (15)C61—C11—C71—O71116.9 (2)
C6—C1—C7—O720.3 (2)C61—C11—C71—O721163.64 (15)
C6—C1—C2—O2177.72 (14)C71—C11—C21—C31176.18 (14)
C7—C1—C2—C3178.49 (14)C11—C21—C31—C410.8 (2)
C2—C1—C6—C51.1 (2)C21—C31—C41—C510.8 (2)
C7—C1—C6—C5179.08 (13)C21—C31—C41—N41176.55 (13)
C6—C1—C2—C31.6 (2)C31—C41—C51—C611.5 (2)
O2—C2—C3—C4178.58 (14)N41—C41—C51—C61175.86 (13)
C1—C2—C3—C40.8 (2)C41—C51—C61—C110.6 (2)
C2—C3—C4—C50.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O710.78 (2)1.91 (2)2.6089 (18)149 (2)
N41—H41A···O52i0.84 (2)1.93 (2)2.7589 (19)170 (2)
N41—H41B···O53ii0.86 (3)2.06 (2)2.7959 (19)142 (2)
N41—H41B···O520.86 (3)2.53 (3)2.8721 (19)104 (2)
N41—H41C···O51iii0.93 (2)1.84 (2)2.7192 (19)156 (2)
O72—H72···O71iv0.77 (3)1.92 (3)2.6923 (17)175 (3)
O721—H721···O711v0.98 (4)1.66 (4)2.6303 (19)172 (3)
C6—H6···O510.932.522.8932 (19)105
Symmetry codes: (i) x+1/2, y+3/2, z+1; (ii) x+1/2, y1/2, z+1/2; (iii) x, y1, z; (iv) x+1, y+2, z+1; (v) x+1, y, z+3/2.
 

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