2-Benz­yloxy-1-naphthaldehyde

Gao, R.; Li, W.-H.; Liu, P.; Wang, P.-A.

doi:10.1107/S1600536809004486

Volume 65
Part 3
Page o534
March 2009

Received 25 December 2008
Accepted 7 February 2009
Online 18 February 2009

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.006 Å
R = 0.084
wR = 0.285
Data-to-parameter ratio = 12.5
Details

2-Benzyloxy-1-naphthaldehyde

Rong Gao,^a Wen-Hong Li,^a Peng Liu ^b and Ping-An Wang ^b ^*

^aDepartment of Chemical Engineering, Northwest University, Taibai North Road 229, 710069 Xi-An, People's Republic of China, and ^bDepartment of Chemistry, School of Pharmacy, Fourth Military Medical University, Changle West Road 17, 710032 Xi-An, People's Republic of China
Correspondence e-mail: ping_an1718@yahoo.com.cn

In the title compound, C₁₈H₁₄O₂, the dihedral angle between the phenyl and naphthyl ring systems is 21.8 (3)°. The packing of molecules in the crystal structure is stabilized by weak intermolecular C-HO hydrogen bonds.

Related literature

For the preparation of 2-benzyloxy-1-naphthaldehyde, see: Quideau et al. (2001). For synthetic use of the title compound, see: Knight & Little (2001).

Experimental

Crystal data

C₁₈H₁₄O₂
M_r = 262.29
Monoclinic, P 2₁ /c
a = 10.427 (7) Å
b = 8.128 (6) Å
c = 15.787 (11) Å
= 94.746 (11)°
V = 1333.3 (16) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 296 K
0.39 × 0.26 × 0.16 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.968, T_max = 0.987
5088 measured reflections
2262 independent reflections
1354 reflections with I > 2(I)
R_int = 0.038

Refinement

R[F² > 2(F²)] = 0.084
wR(F²) = 0.285
S = 1.04
2262 reflections
181 parameters
H-atom parameters constrained
_max = 0.41 e Å^-3
_min = -0.53 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C12-H12AO1ⁱ	0.97	2.48	3.381 (4)	155
C14-H14O1ⁱ	0.93	2.72	3.544 (5)	148
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); 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: Mercury (Macrae et al., 2006) and CAMERON (Watkin et al., 1996).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WN2303 ).

Acknowledgements

We thank the Natural Science Foundation of China (grant No. 20802092) for financial support.

References

Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Knight, D. W. & Little, P. B. (2001). J. Chem. Soc. Perkin Trans. 1, pp. 1771-1777.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.
Quideau, S., Pouységu, L., Oxoby, M. & Looney, M. A. (2001). Tetrahedron, 57, 319-329.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, Oxford, England.

organic compounds