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Volume 68 
Part 1 
Page o85  
January 2012  

Received 23 November 2011
Accepted 2 December 2011
Online 10 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.009 Å
R = 0.082
wR = 0.268
Data-to-parameter ratio = 15.9
Details
Open access

(E)-2-[(1-Benzylpiperidin-4-yl)iminomethyl]phenol

aState Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing 210093, People's Republic of China, and bSchool of Life Science and Technology, University of Electronic Science and Technology of China, Chengdu 610054, People's Republic of China
Correspondence e-mail: fangrq@uestc.edu.cn

There are two molecules in the asymmetric unit of the title compound, C19H22N2O. Both molecules have an E conformation about their C=N bonds and both piperdine rings adopt chair conformations with their N atoms adopting pyramidal geometries [bond angle sums = 329.8 (4) and 330.2 (4)°]. Both molecules feature an intramolecular O-H...N hydrogen bond, which generates an S(6) ring. The dihedral angles between the phenyl and benzene ring planes are 45.97 (18) and 66.0 (2)°. Short O-H...O contacts occur in the crystal.

Related literature

For a related structure, see: Stilinovic et al. (2008[Stilinovic, V., Cincic, D. & Kaitner, B. (2008). Acta. Chim. Solv. 55, 874-879.]).

[Scheme 1]

Experimental

Crystal data
  • C19H22N2O

  • Mr = 294.39

  • Monoclinic, P 21 /c

  • a = 10.603 (2) Å

  • b = 9.6330 (19) Å

  • c = 32.595 (7) Å

  • [beta] = 95.60 (3)°

  • V = 3313.3 (11) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 293 K

  • 0.40 × 0.40 × 0.20 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.971, Tmax = 0.986

  • 6837 measured reflections

  • 6473 independent reflections

  • 2764 reflections with I > 2[sigma](I)

  • Rint = 0.117

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.082

  • wR(F2) = 0.268

  • S = 1.09

  • 6473 reflections

  • 406 parameters

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

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...N1 1.01 (8) 1.73 (7) 2.597 (5) 141 (6)
O2-H2A...N3 1.05 (7) 1.66 (7) 2.588 (6) 144 (5)
O1-H1...O1i 1.01 (8) 2.49 (7) 2.869 (7) 102 (5)
Symmetry code: (i) -x+1, -y+1, -z+2.

Data collection: CAD-4 Software (Enraf-Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); 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.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6532 ).


Acknowledgements

We are grateful to the China Postdoctoral Science Foundation (20110491380) and the Fundamental Research Funds for the Central Universities (ZYGX2009J085) for support.

References

Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Stilinovic, V., Cincic, D. & Kaitner, B. (2008). Acta. Chim. Solv. 55, 874-879.  [ChemPort]


Acta Cryst (2012). E68, o85  [ doi:10.1107/S160053681105197X ]

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