[2-(2-Chloro­phen­yl)-2-hy­droxy­eth­yl](isoprop­yl)ammonium 4-hy­droxy­benzoate

Ling Zhou; Yang Guang Qi; Ge Zhang; Yu Yun Xu; Hai Feng

doi:10.1107/S1600536810051536

. 2010 Dec 18;67(Pt 1):o192. doi: 10.1107/S1600536810051536

[2-(2-Chlorophenyl)-2-hydroxyethyl](isopropyl)ammonium 4-hydroxybenzoate

Ling Zhou ^a, Yang Guang Qi ^a, Ge Zhang ^a, Yu Yun Xu ^a, Hai Feng ^a,^*

PMCID: PMC3050334 PMID: 21522694

Abstract

The title molecular salt, C₁₁H₁₇ClNO⁺·C₇H₅O₃ ⁻, was obtained by the reaction of racemic clorprenaline and 4-hydroxybenzoic acid. In the crystal, the components are connected by O—H⋯O and N—H⋯O hydrogen bonds, resulting in a two-dimensional hydrogen-bonded network.

Related literature

For related structures, see: Takwale & Pant (1971 ▶); Tang et al. (2009 ▶). For hydrogen bonding, see: Feng et al. (2010 ▶).

Experimental

Crystal data

C₁₁H₁₇ClNO⁺·C₇H₅O₃ ⁻
M _r = 351.82
Monoclinic,
a = 9.4033 (4) Å
b = 12.2591 (4) Å
c = 15.9290 (7) Å
β = 96.144 (1)°
V = 1825.68 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 296 K
0.50 × 0.38 × 0.21 mm

Data collection

Rigaku R-AXIS RAPID/ZJUG diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.894, T _max = 0.953
17614 measured reflections
4131 independent reflections
2891 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.110
S = 1.00
4131 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Data collection: PROCESS-AUTO (Rigaku/MSC, 2006) ▶; cell refinement: PROCESS-AUTO ▶; data reduction: CrystalStructure (Rigaku/MSC, 2007) ▶; 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, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810051536/ds2076sup1.cif

e-67-0o192-sup1.cif^{(20.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051536/ds2076Isup2.hkl

e-67-0o192-Isup2.hkl^{(198.4KB, 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—H1B⋯O2	0.90	1.91	2.8090 (18)	177
N1—H1A⋯O3ⁱ	0.90	1.87	2.7671 (18)	178
O1—H101⋯O2ⁱ	0.82	1.94	2.7568 (16)	174
O4—H401⋯O3ⁱⁱ	0.82	1.86	2.6601 (18)	165

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

Acknowledgments

This project was supported by the Zhejiang Science and Technology Department Foundation of China (grant No. 2007 C21127) and the Key Scientific and Technological Research Project of Science and Technology Department of Zhejiang Province of China (grant No. 2008 C12051).

supplementary crystallographic information

Comment

A recent study reports the structure of N-[2-(2-chlorophenyl)-2-hydroxyethyl]- propan-2-aminium-4-methylbenzoate (Feng et al., 2010), which was synthesized by p-Toluic acid and clorprenaline (Tang et al., 2009). In the present study, reaction of 4-Hydroxybenzoic acid instead of p-Toluic acid with racemic clorprenaline yields the title compound, (I) following a similar synthetic procedure.

In (I), the clorprenaline molecule and the 4-Hydroxybenzoic acid molecule are linked to each other by the N—H···O and the O—H···O hydogen bonds (Fig. 1 & Table 1). The clorprenaline in (I) are twisted moderately as compared with those of other compounds. The C(12)-O(2) distance of 1.257 (2)Å is much shorter than the similar distance of 1.292 (8)Å (Takwale et al., 1971). The C(9)-N(1) distance of 1.509 (2)Å is longer than the value of the similar bond distance of 1.473 (4)Å (Tang et al., 2009b) and comparable to the similar bond distance of 1.503 (2)Å (Feng et al., 2010). The C(1)—C(6)—C(7)—C(8) torsion angle of 95.72 (19)° is larger than the value of the C(7)—C(2)—C(1)—C(8) torsion angle of 91.9 (2)° (Tang et al., 2009).

Experimental

Racemic clorprenaline was prepared from clorprenaline hydrochloride purchased from ShangHai Shengxin Medicine & Chemical Co., Ltd. ShangHai, China. Clorprenaline hydrochloride and NaOH in a molar ratio of 1:1 were mixed and dissolved in a methanol-water solution (1:1 v/v). The precipitate formed was filtered off, washed with water and dried. It was used without further purification. Racemic clorprenaline (0.5 g, 0.0023 mol) was dissolved in methanol (6 ml) and then 4-Hydroxybenzoic acid (0.29 g, 0.0023 mol) was added.The mixture was dissolved by stirring for 1h at room temperature. The resulting solution was concentrated at ambient temperature. Colorless crystals of (I) were separated from the solution in about 68% yield after two day.