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Volume 69 
Part 5 
Page o627  
May 2013  

Received 30 December 2012
Accepted 24 March 2013
Online 5 April 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.045
wR = 0.130
Data-to-parameter ratio = 15.3
Details
Open access

9-(2-Chlorobenzylidene)anthracen-10(9H)-one

aDepartment of Chemistry, College of Sciences, King Saud University, PO Box 2455, Riyadh 11451, Saudi Arabia, and bDepartment of Physics, The Madura College, Madurai 625 011, India
Correspondence e-mail: ambujasureshj@yahoo.com

In the title compound, C21H13ClO, the central anthracene system is distorted towards a boat conformation and the outer rings are not coplanar with the central ring [dihedral angles = 7.79 (1) and 11.90 (1)°]. The crystal structure features inversion dimers with graph-set motif R22(18) formed by C-H...O interactions.

Related literature

For ring conformations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For anthracene derivatives see: Alston et al. (1979[Alston, P. V., Ottenbrite, R. M. & Newby, J. (1979). J. Org. Chem. 44, 4939-4943.]); Kaplan & Conroy (1963[Kaplan, F. & Conroy, H. (1963). J. Org. Chem. 28, 1593-1596.]); Meek et al. (1960[Meek, J. S., Wilgus, D. R. & Dann, J. R. (1960). J. Am. Chem. Soc. 82, 2566-2569.]); Singh & Ningombom (2010[Singh, M. D. & Ningombom, A. (2010). Indian J. Chem. Sect. B, 49, 789-794.]); Verma & Singh (1977[Verma, S. M. & Singh, M. D. (1977). J. Org. Chem. 42, 3736-3740.]). For hydrogen bonding, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C21H13ClO

  • Mr = 316.76

  • Triclinic, [P \overline 1]

  • a = 7.9106 (10) Å

  • b = 8.3598 (10) Å

  • c = 12.6906 (15) Å

  • [alpha] = 82.813 (7)°

  • [beta] = 83.979 (7)°

  • [gamma] = 67.741 (6)°

  • V = 769.09 (16) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.25 mm-1

  • T = 293 K

  • 0.21 × 0.19 × 0.17 mm

Data collection
  • Bruker Kappa APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.]) Tmin = 0.967, Tmax = 0.974

  • 11698 measured reflections

  • 3182 independent reflections

  • 2715 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.130

  • S = 1.06

  • 3182 reflections

  • 208 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.50 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C17-H17...O1i 0.93 2.60 3.482 (2) 159
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KJ2220 ).


Acknowledgements

This project was supported by Research Center, Deanship of Scientific Research, College of Science, King Saud University.

References

Alston, P. V., Ottenbrite, R. M. & Newby, J. (1979). J. Org. Chem. 44, 4939-4943.  [CrossRef] [ChemPort]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Kaplan, F. & Conroy, H. (1963). J. Org. Chem. 28, 1593-1596.  [CrossRef] [ChemPort]
Meek, J. S., Wilgus, D. R. & Dann, J. R. (1960). J. Am. Chem. Soc. 82, 2566-2569.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Singh, M. D. & Ningombom, A. (2010). Indian J. Chem. Sect. B, 49, 789-794.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Verma, S. M. & Singh, M. D. (1977). J. Org. Chem. 42, 3736-3740.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o627  [ doi:10.1107/S160053681300809X ]

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