3-Hy­droxy­anilinium p-toluene­sulfonate

Impichira Pykkat Bincy; Rengasamy Gopalakrishnan

doi:10.1107/S1600536813018692

. 2013 Jul 20;69(Pt 8):o1277. doi: 10.1107/S1600536813018692

3-Hydroxyanilinium p-toluenesulfonate

Impichira Pykkat Bincy ^a, Rengasamy Gopalakrishnan ^a,^*

PMCID: PMC3793772 PMID: 24109359

Abstract

The asymmetric unit of the title salt, C₆H₈NO⁺·C₇H₇O₃S⁻, contains two cations and two anions. In the crystal, the cations and anions are linked through extensive N—H⋯O and O—H⋯O hydrogen-bonding interactions, which result in R ₄ ⁴(18) and R ₂ ¹(4) ring motifs, forming a three-dimensional network.

Related literature

For related structures of 4-toluenesulfonate salts, see: Koshima et al. (2004 ▶); Biradha & Mahata (2005 ▶); Sivakumar et al. (2012 ▶). graphic file with name e-69-o1277-scheme1.jpg

Experimental

Crystal data

C₆H₈NO⁺·C₇H₇O₃S⁻
M _r = 281.32
Triclinic,
a = 9.5775 (3) Å
b = 10.8224 (3) Å
c = 14.1445 (4) Å
α = 96.787 (2)°
β = 109.701 (1)°
γ = 91.324 (2)°
V = 1367.50 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.910, T _max = 0.953
32207 measured reflections
8651 independent reflections
6679 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.122
S = 1.03
8651 reflections
372 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813018692/kp2454sup1.cif

e-69-o1277-sup1.cif^{(33.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813018692/kp2454Isup2.hkl

e-69-o1277-Isup2.hkl^{(423.1KB, hkl)}

Click here for additional data file.^{(5KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813018692/kp2454Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7⋯O6ⁱ	0.82	1.95	2.7657 (16)	173 (2)
N2—H2C⋯O4ⁱ	0.89 (1)	2.06 (1)	2.9441 (18)	170 (2)
N2—H2B⋯O3ⁱ	0.89 (1)	2.31 (2)	2.9020 (17)	124 (2)
N2—H2A⋯O3ⁱⁱ	0.90 (1)	1.89 (1)	2.7784 (18)	170 (2)
N2—H2B⋯O5ⁱⁱ	0.89 (1)	2.20 (2)	2.9395 (19)	141 (2)
N1—H1B⋯O5ⁱⁱⁱ	0.89 (1)	2.15 (2)	2.9406 (19)	147 (2)
N1—H1B⋯O6ⁱⁱⁱ	0.89 (1)	2.32 (2)	3.1087 (19)	147 (2)
N1—H1C⋯O2^iv	0.89 (1)	1.86 (1)	2.7410 (18)	177 (2)
O8—H8⋯O1	0.82	1.94	2.7216 (17)	160
N1—H1A⋯O1	0.90 (1)	1.95 (1)	2.8007 (17)	158 (2)

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

Acknowledgments

The authors thank thank Dr Babu Varghese, Senior Scientific Officer, SAIF, IIT Madras, Chennai, India, for the data collection.

supplementary crystallographic information

Comment

The asymmetric unit of the title salt (Fig.1) contains two hydroxyanilinium cations [C₆H₈N₁O₁]⁺ and two 4-toluenesulfonate anions [C₇H₇O₃S₁]^-. The aminophenol molecule exists as hydroxyanilinium cation due to the protonation. The 4-toluenesulfonic acid exists as 4-toluenesulfonate due to a proton transfer. The hydroxyl oxygen atoms O7 and O8 attached to the phenyl ring deviate from the ring plane by 0.0528 (1)° and 0.0157 (1)Å, respectively. The crystal packing is stabilsed by intermolcular N—H···O and O—H···O hydrogen bonds (Table 1, Fig.2) involving R⁴₄(18), R¹₂(4) ring motifs.

Experimental

The title compound was obtained by addition of 3-aminophenol and 4-toluenesulfonic acid in an equimolar ratio using methanol as solvent. After a filtration of resulting solution into a clean beaker, which was covered and kept at room temperature for slow evaporation. After a period of 2 weeks, block-like colourless crystals suitable for X-ray diffraction analysis were obtained.