N-[2-(2-Chloro­phen­yl)-2-hy­droxy­eth­yl]propan-2-aminium benzoate

Hai Feng; Ya Jian Zhou; Bin Tao Xing; Yang Guang Qi; Zheng Wu

doi:10.1107/S1600536810040274

. 2010 Oct 23;66(Pt 11):o2910. doi: 10.1107/S1600536810040274

N-[2-(2-Chlorophenyl)-2-hydroxyethyl]propan-2-aminium benzoate

Hai Feng ^a,^*, Ya Jian Zhou ^a, Bin Tao Xing ^a, Yang Guang Qi ^a, Zheng Wu ^b

PMCID: PMC3009367 PMID: 21589084

Abstract

In the title compound, C₁₁H₁₇ClNO⁺·C₇H₅O₂ ⁻, obtained by the reaction of chlorprenaline {or 1-(2-chlorophenyl)-2-[(1-methylethyl)amino]ethanol} and benzoic acid, the chlorprenaline is twisted moderately [C—C—C—C torsion angle = −76.00 (17)°] compared with related compounds. The molecules as usual form dimers. In the crystal structure, the two components are connected by classical O—H⋯O and N—H⋯O hydrogen bonds.

Related literature

For related structures, see: Feld et al. (1981 ▶); Feng et al. (2010 ▶); Tang et al. (2009a ▶,b ▶).

Experimental

Crystal data

C₁₁H₁₇ClNO⁺·C₇H₅O₂ ⁻
M _r = 335.82
Monoclinic,
a = 7.8343 (3) Å
b = 13.1260 (5) Å
c = 17.7308 (7) Å
β = 94.330 (1)°
V = 1818.11 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 296 K
0.53 × 0.48 × 0.46 mm

Data collection

Rigaku R-AXIS RAPID/ZJUG diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.871, T _max = 0.904
17400 measured reflections
4123 independent reflections
3186 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.110
S = 1.00
4123 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.32 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 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810040274/rk2237sup1.cif

e-66-o2910-sup1.cif^{(20KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040274/rk2237Isup2.hkl

e-66-o2910-Isup2.hkl^{(198KB, 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⋯O2	0.90	1.85	2.7231 (15)	162
O1—H1⋯O3	0.82	1.93	2.7219 (15)	162
N1—H1B⋯O3ⁱ	0.90	1.88	2.7710 (15)	169

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the Key Scientific and Technological Research Project of the Science and Technology Department of Zhejiang Province of China (grant No. 2009 C32078).

supplementary crystallographic information

Comment

A recent study reports the structure of bis{N-[2-(2-chlorophenyl)-2-hydroxyethyl]propan-2-aminium} oxalate (Tang et al., 2009b), which was synthesized by oxalic acid and chlorprenaline (Tang et al., 2009a). Here using benzoic acid instead of oxalic acid and following a similar synthetic procedure yields the title compound, I.

In I (Fig. 1), the chlorprenaline molecule and the benzoic acid molecule are linked to each other by the N1—H1A···O2 hydogen bond (2.7231 (15)Å) and the O1—H1···O3 hydogen bond (2.7219 (15)Å) (Fig. 2 & Table 1). The chlorprenaline in I are twisted moderately as compared with those of other compounds. The C12—O2 distance of 1.2456 (18)Å is much shorter than the similar distance of 1.2675 (15)Å (Feld et al., 1981). The C1—C6—C7—C8 torsion angle of -76.00 (17)° (104.0 (17)°) is larger than the value of the similar torsion angle of 91.9 (2)° (Tang et al., 2009a). The C9—N1 distance of 1.5096 (17)Å is longer than the value of the similar bond distance of 1.473 (4)Å (Tang et al., 2009b), as similar as the value of the similar bond distance of 1.503 (2)Å (Feng et al., 2010).

Classical hydrogen bonds (O—H···O and N—H···O) are found in the cystal structure (Fig. 2 & Table 1) are essential forces in crystal formation.

Experimental

Racemic chlorprenaline was prepared by chlorprenaline hydrochloride purchased from ShangHai Shengxin Medicine & Chemical Co., Ltd. ShangHai, China. chlorprenaline 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 chlorprenaline (0.5 g, 0.0023 mol) was dissolved in methanol (5 ml) and then Benzoic acid (0.3 g, 0.0023 mol) was added. The mixture was dissovled by heating to 323 K where a clear solution resulted. The resulting solution was concentrated at ambient temperature. Colourless crystals of I separated from the solution in about 68% yield after one day.