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Volume 64 
Part 12 
Page o2497  
December 2008  

Received 9 October 2008
Accepted 25 November 2008
Online 29 November 2008

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Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.002 Å
R = 0.033
wR = 0.096
Data-to-parameter ratio = 13.0
Details
Open access

(4-Chlorophenyl)(2-hydroxy-7-methoxynaphthalen-1-yl)methanone

Ryosuke Mitsui,a Kosuke Nakaema,a Keiichi Noguchib and Noriyuki Yonezawaa*

aDepartment of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology, 2-24-16 Naka-machi, Koganei, Tokyo 184-8588, Japan, and bInstrumentation Analysis Center, Tokyo University of Agriculture & Technology, 2-24-16 Naka-machi, Koganei, Tokyo 184-8588, Japan
Correspondence e-mail: yonezawa@cc.tuat.ac.jp

The title compound, C18H13ClO3, has an intramolecular O-H...O=C hydrogen bond between the carbonyl group and the hydroxy substituent on the naphthalene ring system. The angle between the C=O bond plane and the naphthalene ring system is relatively small [20.96 (8)°]. The angle between the benzene ring and the carbonyl group is rather large [35.65 (9)°] compared to that in an analogous compound [3.43 (11)°] having a methoxy group instead of a hydroxy substituent.

Related literature

For the structures of closely related compounds, see: Nakaema et al. (2007[Nakaema, K., Okamoto, A., Noguchi, K. & Yonezawa, N. (2007). Acta Cryst. E63, o4120.], 2008[Nakaema, K., Watanabe, S., Okamoto, A., Noguchi, K. & Yonezawa, N. (2008). Acta Cryst. E64, o807.]); Mitsui et al. (2008[Mitsui, R., Nakaema, K., Noguchi, K., Okamoto, A. & Yonezawa, N. (2008). Acta Cryst. E64, o1278.]).

[Scheme 1]

Experimental

Crystal data

  • C18H13ClO3

  • Mr = 312.73

  • Orthorhombic, P b c a

  • a = 17.8030 (3) Å

  • b = 8.68121 (10) Å

  • c = 18.8683 (3) Å

  • V = 2916.14 (8) Å3

  • Z = 8

  • Cu K[alpha] radiation

  • [mu] = 2.41 mm-1

  • T = 123 K

  • 0.60 × 0.15 × 0.05 mm
Data collection

  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: numerical (NUMABS; Higashi, 1999[Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.485, Tmax = 0.886

  • 49864 measured reflections

  • 2669 independent reflections

  • 2347 reflections with I > 2[sigma](I)

  • Rint = 0.033
Refinement

  • R[F2 > 2[sigma](F2)] = 0.033

  • wR(F2) = 0.096

  • S = 1.08

  • 2669 reflections

  • 205 parameters

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

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2...O1 0.94 (2) 1.71 (2) 2.5573 (16) 148 (2)

Data collection: PROCESS-AUTO (Rigaku, 1998[Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004[Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); program(s) used to solve structure: SIR2004 (Burla et al., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.]); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2069 ).

Acknowledgements

This work was financially supported by SEIKI KOGYO CO., Ltd, Tokorozawa, Saitama, Japan.

References

Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.  [ISI] [CrossRef] [ChemPort] [details]
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.
Mitsui, R., Nakaema, K., Noguchi, K., Okamoto, A. & Yonezawa, N. (2008). Acta Cryst. E64, o1278.  [CSD] [CrossRef] [details]
Nakaema, K., Okamoto, A., Noguchi, K. & Yonezawa, N. (2007). Acta Cryst. E63, o4120.  [CSD] [CrossRef] [details]
Nakaema, K., Watanabe, S., Okamoto, A., Noguchi, K. & Yonezawa, N. (2008). Acta Cryst. E64, o807.  [CSD] [CrossRef] [details]
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]

Acta Cryst (2008). E64, o2497  [ doi:10.1107/S1600536808039603 ]

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