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

Fang, R.-Q.; Xiao, Z.-P.; Zuo, Y.

doi:10.1107/S160053681105197X

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 (C-C) = 0.009 Å
R = 0.082
wR = 0.268
Data-to-parameter ratio = 15.9
Details

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

Rui-Qin Fang,^a,^b ^* Zhu-Ping Xiao ^a and Yun Zuo ^b

^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-HN 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-HO contacts occur in the crystal.

Related literature

For a related structure, see: Stilinovic et al. (2008).

Experimental

Crystal data

C₁₉H₂₂N₂O
M_r = 294.39
Monoclinic, P 2₁ /c
a = 10.603 (2) Å
b = 9.6330 (19) Å
c = 32.595 (7) Å
= 95.60 (3)°
V = 3313.3 (11) Å³
Z = 8
Mo K radiation
= 0.07 mm^-1
T = 293 K
0.40 × 0.40 × 0.20 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.971, T_max = 0.986
6837 measured reflections
6473 independent reflections
2764 reflections with I > 2(I)
R_int = 0.117
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2(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
_max = 0.22 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1N1	1.01 (8)	1.73 (7)	2.597 (5)	141 (6)
O2-H2AN3	1.05 (7)	1.66 (7)	2.588 (6)	144 (5)
O1-H1O1ⁱ	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); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); 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 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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Stilinovic, V., Cincic, D. & Kaitner, B. (2008). Acta. Chim. Solv. 55, 874-879.

organic compounds