N-[2-(2-Chloro­phen­yl)-2-hy­droxy­eth­yl]propan-2-aminium 4-methyl­benzoate

Hai Feng; Bin Tao Xing; Xin Huang; Ya Jian Zhou; Ying Song

doi:10.1107/S1600536810033878

. 2010 Sep 25;66(Pt 10):o2605. doi: 10.1107/S1600536810033878

N-[2-(2-Chlorophenyl)-2-hydroxyethyl]propan-2-aminium 4-methylbenzoate

Hai Feng ^a,^*, Bin Tao Xing ^a, Xin Huang ^a, Ya Jian Zhou ^a, Ying Song ^a

PMCID: PMC2983265 PMID: 21587582

Abstract

The title compound, C₁₁H₁₇ClNO⁺·C₈H₇O₂ ⁻, was obtained by the reaction of chlorprenaline {or 1-(2-chlorophenyl)-2-[(1-methylethyl)amino]ethanol} and p-toluic acid. The chlorprenaline is twisted moderately with a C—C—C—C torsion angle of 109.6 (2)°. The two molecules are linked by classical O—H⋯O and N—H⋯O hydrogen bonds. Further N—H⋯O hydrogen bonds link two of these units into dimers.

Related literature

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

Experimental

Crystal data

C₁₁H₁₇ClNO⁺·C₈H₇O₂ ⁻
M _r = 349.84
Monoclinic,
a = 8.5966 (4) Å
b = 8.1288 (3) Å
c = 26.8949 (12) Å
β = 91.600 (1)°
V = 1878.68 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 296 K
0.37 × 0.30 × 0.22 mm

Data collection

Rigaku R-AXIS RAPID/ZJUG CCD diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.913, T _max = 0.953
27924 measured reflections
4271 independent reflections
2763 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.125
S = 1.00
4271 reflections
222 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.31 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/S1600536810033878/rk2225sup1.cif

e-66-o2605-sup1.cif^{(20.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033878/rk2225Isup2.hkl

e-66-o2605-Isup2.hkl^{(205.1KB, 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
O1—H101⋯O3	0.82	1.88	2.6986 (18)	173
N1—H103⋯O2	0.90	1.91	2.7835 (18)	164
N1—H102⋯O3ⁱ	0.90	1.89	2.7824 (19)	174

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Symmetry code: (i) Inline graphic .

Acknowledgments

This project was supported by the Zhejiang Provincial Natural Science Foundation of China (grant No. Y206174).

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 p-toluic acid instead of oxalic acid and following a similar synthetic procedure yields the title compound, I.

In I, the chlorprenaline molecule and the p-toluic molecule are linked to each other by the classical N1—H103···O2 hydogen bond [2.7835 (18)Å] and the O1—H101···O3 hydogen bond [2.6986 (18)Å] (Fig. 1 & Table 1). The chlorprenaline in I are twisted moderately as compared with those of other compounds. The C7—C2—C1—C8 torsion angle of 109.6 (2)° is larger than the value of the similar torsion angle of 91.9 (2)° (Tang et al., 2009a). The C12–O2 distance of 1.248 (2)Å is much shorter than the similar distance of 1.292 (8)Å (Takwale & Pant, 1971). The C9–N1 distance of 1.507 (2)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 O—H···O and N—H···O hydrogen bonds are found in the cystal structure (Fig. 2) 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 (7 ml) and then p-toluylic acid (0.31 g, 0.0023 mol) was added.The mixture was dissovled by heating to 343 K where a clear solution resulted. The resulting solution was concentrated at ambient temperature. Colourless crystals of title compound separated from the solution in about 70% yield after one day.