1,2-Diphenyl-2-[(1-phenyl­eth­yl)amino]­ethanol

Qing-Gao Hou; Chang-Qiu Zhao

doi:10.1107/S1600536812027420

. 2012 Jun 27;68(Pt 7):o2220. doi: 10.1107/S1600536812027420

1,2-Diphenyl-2-[(1-phenylethyl)amino]ethanol

Qing-Gao Hou ^a, Chang-Qiu Zhao ^a,^*

PMCID: PMC3394014 PMID: 22798879

Abstract

In the molecule of the title compound, C₂₂H₂₃NO, there are two chiral atoms (R* for the C atom attached to the OH group and S* for the C atom attached to the phenyl ring). In the crystal, neighbouring molecules are connected into a chain along the b axis by N—H⋯O hydrogen bonds.

Related literature

For background to the synthesis of chiral organic compounds, see: Alcaide et al. (1981 ▶)

Experimental

Crystal data

C₂₂H₂₃NO
M _r = 317.41
Orthorhombic,
a = 6.307 (4) Å
b = 12.801 (7) Å
c = 22.490 (12) Å
V = 1815.7 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 298 K
0.50 × 0.29 × 0.21 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.966, T _max = 0.985
11619 measured reflections
4471 independent reflections
2660 reflections with I > 2σ(I)
R _int = 0.071

Refinement

R[F ² > 2σ(F ²)] = 0.059
wR(F ²) = 0.160
S = 1.00
4471 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; 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 datablock(s) I, global. DOI: 10.1107/S1600536812027420/ds2194sup1.cif

e-68-o2220-sup1.cif^{(19.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812027420/ds2194Isup2.hkl

e-68-o2220-Isup2.hkl^{(219.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812027420/ds2194Isup3.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
N1—H1A⋯O1ⁱ	0.90	2.04	2.908 (2)	160

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank the National Natural Science Foundation of China (grant No. 20772055) for the financial support of this study.

supplementary crystallographic information

Comment

In the molecule of chiral title compound 1,2-dipheny1-2-((1-phenylethyl)amino)ethanol,which derived from (R_p) phenylamine,accroding to the Cram rules and the molecular structure, two chiral atoms: C1(R*) and C8(S*) are observed. In the crystal structure, intermolecular N—H···O hydrogen bonds connect the same neighbour molecules into a one-dimensional chain,giving rise along b axis. The angle of C1-O1-H1,O1-N1-H1A, C8-N1-H1A and C15-N1-H1A are 109.47°, 160.4°, 108.11° and 108.19°. The torsion angle of O1-C1-C8-N1 is 56.46 (0.22)°. The arrangement between two neighbour molecules are same.

Experimental

Benzil (0.75 g, 3.6 mmol) was added to a stirred ethanol solution of R-phenylethylamine (0.87 g, 3.96 mmol) in a round-bottomed flask under a nitrogen atmosphere and heated until ethanol refluxed. This reaction took about 31 h. In the ice bath environment, sodium borohydride (0.27 g, 7.92 mmol) was added to the mixture in batches. Then drained ethanol, white solid was obtained. The crude product was extracted with dichloromethane three times. The organic phase was dried over anhydrous magnesium sulfate and then evaporated. The pure product was obtained after recrystallized with petroleum ether. Single crystal of the title compound suitable for X–ray diffraction were obtained by slow evaporation of petroleum ether solution of the title compound.