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Volume 67 
Part 2 
Page o373  
February 2011  

Received 31 December 2010
Accepted 6 January 2011
Online 12 January 2011

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Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.006 Å
R = 0.082
wR = 0.161
Data-to-parameter ratio = 15.5
Details
Open access

3-Chloro-N'-[(2-hydroxynaphthalen-1-yl)methylidene]benzohydrazide

Tian-Yi Lia* and Wei Lia

aSchool of Chemical Engineering, Changchun University of Technology, Changchun 130012, People's Republic of China
Correspondence e-mail: cooperationwell@126.com

The title compound, C18H13ClN2O2, was prepared by the reaction of 2-hydroxy-1-naphthaldehyde with 3-chlorobenzohydrazide in methanol. An intramolecular O-H...N hydrogen bond influences the molecular conformation; the benzene ring and naphthyl ring system form a dihedral angle of 17.1 (3)°. In the crystal, intermolecular N-H...O hydrogen bonds link the molecules into chains propagated in [101].

Related literature

For Schiff base compounds, see: Bessy et al. (2006[Bessy, R. B. N., Prathapachandra, K. M. R. & Suresh, E. (2006). Struct. Chem. 17, 201-208.]); Podyachev et al. (2007[Podyachev, S. N., Litvinov, I. A., Shagidullin, R. R., Buzykin, B. I., Bauer, I., Osyanina, D. V., Avvakumova, L. V., Sudakova, S. N., Habicher, W. D. & Konovalov, A. I. (2007). Spectrochim. Acta Part A, 66, 250-261.]); Raj & Kurup (2007[Raj, B. N. B. & Kurup, M. R. P. (2007). Spectrochim. Acta Part A, 66, 898-903.]); Pouralimardan et al. (2007[Pouralimardan, O., Chamayou, A.-C., Janiak, C. & Hosseini-Monfared, H. (2007). Inorg. Chim. Acta, 360, 1599-1608.]); Bacchi et al. (2006[Bacchi, A., Carcelli, M., Pelizzi, G., Solinas, C. & Sorace, L. (2006). Inorg. Chim. Acta, 359, 2275-2280.]); Dinda et al. (2002[Dinda, R., Sengupta, P., Ghosh, S., Mayer-Figge, H. & Sheldrick, W. S. (2002). J. Chem. Soc. Dalton Trans. pp. 4434-4439.]). For reference bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For details of the synthesis, see: Zhu (2010[Zhu, H.-Y. (2010). Acta Cryst. E66, o2562.]).

[Scheme 1]

Experimental

Crystal data

  • C18H13ClN2O2

  • Mr = 324.75

  • Monoclinic, P 21 /n

  • a = 7.158 (2) Å

  • b = 30.886 (3) Å

  • c = 7.3733 (12) Å

  • [beta] = 108.924 (2)°

  • V = 1541.9 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.26 mm-1

  • T = 298 K

  • 0.20 × 0.20 × 0.18 mm
Data collection

  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.950, Tmax = 0.955

  • 8306 measured reflections

  • 3288 independent reflections

  • 1635 reflections with I > 2[sigma](I)

  • Rint = 0.062
Refinement

  • R[F2 > 2[sigma](F2)] = 0.082

  • wR(F2) = 0.161

  • S = 1.04

  • 3288 reflections

  • 212 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.35 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2...O2i 0.90 (3) 1.99 (2) 2.860 (4) 162 (4)
O1-H1...N1 0.82 1.85 2.574 (4) 146
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: CV5033 ).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bacchi, A., Carcelli, M., Pelizzi, G., Solinas, C. & Sorace, L. (2006). Inorg. Chim. Acta, 359, 2275-2280.  [ChemPort]
Bessy, R. B. N., Prathapachandra, K. M. R. & Suresh, E. (2006). Struct. Chem. 17, 201-208.  [ChemPort]
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Dinda, R., Sengupta, P., Ghosh, S., Mayer-Figge, H. & Sheldrick, W. S. (2002). J. Chem. Soc. Dalton Trans. pp. 4434-4439.  [CrossRef]
Podyachev, S. N., Litvinov, I. A., Shagidullin, R. R., Buzykin, B. I., Bauer, I., Osyanina, D. V., Avvakumova, L. V., Sudakova, S. N., Habicher, W. D. & Konovalov, A. I. (2007). Spectrochim. Acta Part A, 66, 250-261.  [ChemPort]
Pouralimardan, O., Chamayou, A.-C., Janiak, C. & Hosseini-Monfared, H. (2007). Inorg. Chim. Acta, 360, 1599-1608.  [ISI] [CSD] [CrossRef] [ChemPort]
Raj, B. N. B. & Kurup, M. R. P. (2007). Spectrochim. Acta Part A, 66, 898-903.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Zhu, H.-Y. (2010). Acta Cryst. E66, o2562.  [CrossRef] [details]

Acta Cryst (2011). E67, o373  [ doi:10.1107/S1600536811000912 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.