(4-Hydroxy­phen­yl)methanaminium 2-(4-sulfanylphen­yl)acetate

Ying-Jie Cai; Xi-Bin Dai; Lian Liu; Jin Li; Hai-Yan Li

doi:10.1107/S1600536809034540

. 2009 Sep 5;65(Pt 10):o2341. doi: 10.1107/S1600536809034540

(4-Hydroxyphenyl)methanaminium 2-(4-sulfanylphenyl)acetate

Ying-Jie Cai ^a, Xi-Bin Dai ^a, Lian Liu ^a, Jin Li ^a, Hai-Yan Li ^a,^*

PMCID: PMC2970201 PMID: 21577812

Abstract

In the title molecular salt, C₇H₁₀NO⁺·C₈H₇O₂S⁻, the crystal structure is stabilized by intermolecular N—H⋯O, O—H⋯N and C—H⋯O hydrogen bonds.

Related literature

For related molecular salts, see: Xia et al. (2003 ▶); He et al. (2008 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₇H₁₀NO⁺·C₈H₇O₂S⁻
M _r = 291.37
Monoclinic,
a = 6.545 (5) Å
b = 14.792 (12) Å
c = 14.868 (11) Å
β = 104.78 (4)°
V = 1391.8 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 293 K
0.32 × 0.28 × 0.26 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.927, T _max = 0.940
6838 measured reflections
2447 independent reflections
1895 reflections with I > 2σ(I)
R _int = 0.061
??? standard reflections every ??? reflections intensity decay: ???%

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.182
S = 1.11
2447 reflections
191 parameters
22 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809034540/hb5068sup1.cif

e-65-o2341-sup1.cif^{(18.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034540/hb5068Isup2.hkl

e-65-o2341-Isup2.hkl^{(120.3KB, hkl)}

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
N1—H1A⋯O1ⁱ	0.845 (19)	1.99 (2)	2.782 (4)	156 (4)
N1—H1C⋯O2ⁱⁱ	0.89 (2)	1.87 (2)	2.752 (4)	169 (5)
N1—H1B⋯O1ⁱⁱⁱ	0.872 (18)	1.885 (19)	2.749 (4)	171 (3)
O3—H3B⋯N1^iv	0.82	2.54	3.267 (4)	149
C6—H6⋯O3ⁱⁱⁱ	0.93	2.60	3.521 (4)	171

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

Acknowledgments

This project was supported by the Education Commission of Hubei Province (D20091703) and the Natural Science Foundation of Hubei Province (2008CDB038).

supplementary crystallographic information

Comment

There has been much research interest in the intermolecular interactions between carboxylic acid and amine. (Xia et al., 2003; He et al., 2008). The title compound (I) is presented in Fig.1, all bond lengths are within normal ranges (Allen et al., 1987) (Table 1). The carboxylate cation and aminium anion are linked via N—H···O, O—H···N and C—H···O intermolecular hydrogen bonds (Table 2) into three network along the a axis. (Fig. 2).

Experimental

A mixture of 2-(4-mercaptophenyl)acetic acid (336 mg, 2 mmol), and 4-(aminomethyl)phenol (246 mg, 2 mmol) was stirred in methanol (10 ml) for 1 h. After keeping the solution in air for 3 d, colourless blocks of (I) were formed.