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Volume 69 
Part 7 
Page o1022  
July 2013  

Received 22 March 2013
Accepted 28 May 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.045
wR = 0.102
Data-to-parameter ratio = 8.0
Details
Open access

2-Methyl-1,1-diphenyl-2-[(4S)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]propan-1-ol

aCollege of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu Province 730070, People's Republic of China
Correspondence e-mail: huylai@163.com

In the title compound, C25H25NO2, the phenyl ring on the 1,3-oxazole ring is disordered over two positions with occupancies of 0.600 (4) and 0.400 (4). The interplanar angle between these two disordered rings is 77.8 (2)°. There is an intramolecular O-H...N hydrogen bond of moderate strength. In the crystal, C-H...[pi] interactions interconnect neighbouring molecules. The absolute structure has been derived from the known absolute structure of the reagents.

Related literature

For the synthesis and applications of oxazolines, see: Ghosh et al. (1998[Ghosh, A. K., Mathivanan, P. & Cappiello, J. (1998). Tetrahedron Asymmetry, 9, 1-45.]); Johnson & Evans (2000[Johnson, J. S. & Evans, D. A. (2000). Acc. Chem. Res. 33, 325-335.]). For the categorization of hydrogen bonds, see: Gilli & Gilli (2009[Gilli, G. & Gilli, P. (2009). The Nature of the Hydrogen Bond. Outline of a Comprehensive Hydrogen Bond Theory, p. 61. International Union of Crystallography. Oxford Science Publications. New York, Oxford: Oxford University Press Inc.]).

[Scheme 1]

Experimental

Crystal data
  • C25H25NO2

  • Mr = 371.46

  • Orthorhombic, P 21 21 21

  • a = 9.5405 (2) Å

  • b = 10.9430 (9) Å

  • c = 19.2901 (6) Å

  • V = 2013.92 (18) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 293 K

  • 0.34 × 0.07 × 0.06 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). SAINT, APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.849, Tmax = 0.977

  • 5590 measured reflections

  • 2428 independent reflections

  • 2103 reflections with I > 2[sigma](I)

  • Rint = 0.040

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.102

  • S = 1.08

  • 2428 reflections

  • 305 parameters

  • 338 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2, Cg3 and Cg4 are the centroids of the C8-C13, C14-C19 and C20-C25 rings, respectively.

D-H...A D-H H...A D...A D-H...A
O2-H2...N6 0.86 (3) 1.89 (3) 2.712 (3) 159 (3)
C1-H1...Cg2i 0.98 2.80 3.771 (3) 173
C2-H2A...Cg2ii 0.97 2.86 3.589 (3) 132
C24B-H24B...Cg3iii 0.93 2.87 3.776 (6) 166
C24B-H24B...Cg4iii 0.93 2.97 3.785 (9) 147
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) x-1, y, z; (iii) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). SAINT, APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). SAINT, APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and DIAMOND (Brandenburg, 2010[Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FB2285 ).


Acknowledgements

This work was supported by the Key Laboratory of Polymer Materials of Gansu Province (Northwest Normal University).

References

Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2008). SAINT, APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Ghosh, A. K., Mathivanan, P. & Cappiello, J. (1998). Tetrahedron Asymmetry, 9, 1-45.  [Web of Science] [CrossRef] [ChemPort]
Gilli, G. & Gilli, P. (2009). The Nature of the Hydrogen Bond. Outline of a Comprehensive Hydrogen Bond Theory, p. 61. International Union of Crystallography. Oxford Science Publications. New York, Oxford: Oxford University Press Inc.
Johnson, J. S. & Evans, D. A. (2000). Acc. Chem. Res. 33, 325-335.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1022  [ doi:10.1107/S1600536813014670 ]

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