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Volume 64 
Part 9 
Page o1725  
September 2008  

Received 11 July 2008
Accepted 4 August 2008
Online 9 August 2008

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Key indicators
Single-crystal X-ray study
T = 291 K
Mean [sigma](C-C) = 0.003 Å
R = 0.050
wR = 0.117
Data-to-parameter ratio = 15.4
Details
Open access

2-(6-Methyl-2-pyridyl)-1,1-diphenylethanol

Wei-Jin Gua* and Bing-Xiang Wanga

aDepartment of Applied Chemistry, Nanjing Normal University, Nanjing 210097, People's Republic of China
Correspondence e-mail: llyyjz@nju.edu.cn

The title compound, C20H19NO, was prepared from 2,6-lutidine and benzophenone. There are two symmetry-independent molecules in the asymmetric unit. Each molecule is involved in one intramolecular O-H...N hydrogen bond. In the crystal structure, helical chains are formed along the b axis by weak [pi]-[pi] interactions between neighbouring molecules [centroid-centroid distances between the pyridyl rings of the two independent molecules = 4.041 (3) and 4.051 (3) Å].

Related literature

For related literature, see: Berg & Holm (1985[Berg, J. M. & Holm, R. H. (1985). J. Am. Chem. Soc. 107, 917-925.]); Dehnicke et al. (2001[Dehnicke, K., Weller, F. & Strahle, J. (2001). Chem. Soc. Rev. 30, 125-135.]); Gibson et al. (2007[Gibson, V. C., Redshaw, C., Clegg, W. & Elsegood, M. R. J. (2007). Polyhedron, 26, 3161-3167.]); Koning et al. (2000[Koning, B., Buter, J., Hulst, R., Stroetinga, R. & Kellogg, R. M. (2000). Eur. J. Org. Chem. pp. 2735-2743.]); Yip et al. (2003[Yip, K.-L., Yu, W.-Y., Chan, P.-M., Zhu, N.-Y. & Che, C.-M. (2003). Dalton Trans, pp. 3556-3566.]).

[Scheme 1]

Experimental

Crystal data

  • C20H19NO

  • Mr = 289.36

  • Monoclinic, P 21 /c

  • a = 13.466 (2) Å

  • b = 8.022 (1) Å

  • c = 30.220 (3) Å

  • [beta] = 102.874 (3)°

  • V = 3182.4 (7) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 291 (2) K

  • 0.30 × 0.26 × 0.24 mm
Data collection

  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.98, Tmax = 0.98

  • 24109 measured reflections

  • 6247 independent reflections

  • 4901 reflections with I > 2[sigma](I)

  • Rint = 0.039
Refinement

  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.116

  • S = 1.02

  • 6247 reflections

  • 405 parameters

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

  • [Delta][rho]max = 0.12 e Å-3

  • [Delta][rho]min = -0.12 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1A...N1 0.96 (2) 1.89 (2) 2.724 (2) 144 (2)
O2-H2A...N2 0.96 (2) 1.92 (2) 2.718 (2) 139 (2)
C18-H18...O2i 0.93 2.70 3.518 (2) 147
C38-H38...O1ii 0.93 2.65 3.472 (2) 147
Symmetry codes: (i) -x, -y+1, -z; (ii) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SMART; data reduction: SAINT (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2078 ).

Acknowledgements

We thank the Natural Science Foundation of the Jiangsu Higher Education Institutions of China (grant No. 07KJD150101) for financial support.

References

Berg, J. M. & Holm, R. H. (1985). J. Am. Chem. Soc. 107, 917-925.  [CrossRef] [ChemPort] [ISI]
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Dehnicke, K., Weller, F. & Strahle, J. (2001). Chem. Soc. Rev. 30, 125-135.  [CrossRef] [ChemPort]
Gibson, V. C., Redshaw, C., Clegg, W. & Elsegood, M. R. J. (2007). Polyhedron, 26, 3161-3167.  [CrossRef] [ChemPort]
Koning, B., Buter, J., Hulst, R., Stroetinga, R. & Kellogg, R. M. (2000). Eur. J. Org. Chem. pp. 2735-2743.  [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Yip, K.-L., Yu, W.-Y., Chan, P.-M., Zhu, N.-Y. & Che, C.-M. (2003). Dalton Trans, pp. 3556-3566.

Acta Cryst (2008). E64, o1725  [ doi:10.1107/S1600536808025026 ]

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