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Volume 69 
Part 2 
Pages o314-o315  
February 2013  

Received 15 January 2013
Accepted 24 January 2013
Online 31 January 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.003 Å
R = 0.049
wR = 0.145
Data-to-parameter ratio = 19.4
Details
Open access

1-(4-{2-[(E)-3-(4-Chlorophenyl)-3-oxoprop-1-en-1-yl]phenoxy}butyl)-1H-indole-3-carbaldehyde

aPost Graduate and Research Department of Physics, Agurchand Manmull Jain College, Chennai 600 114, India, and bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: seshadri_pr@yahoo.com

In the title compound, C28H24ClNO3, the dihedral angles between the central benzene ring and the indole ring system and the chlorobenzene ring are 70.81 (5) and 78.62 (5)°, respectively. The molecular structure is stabilized by a weak intramolecular C-H...O interaction. In the crystal, pairs of C-H...O hydrogen bonds link the molecules into inversion dimers with an R22(14) motif.

Related literature

For the biological activity of indole derivatives, see: Olgen & Coban (2003[Olgen, S. & Coban, T. (2003). Biol. Pharm. Bull. 26, 736-738.]); Ho et al. (1986[Ho, C. Y., Haegman, W. E. & Perisco, F. (1986). J. Med. Chem. 29, 118-121.]); Joshi & Chand (1982[Joshi, K. C. & Chand, P. (1982). Pharmazie, 37, 1-12.]); Rodriguez et al. (1985[Rodriguez, J. G., Temprano, F., Esteban-Calderon, C., Martinez-Ripoll, M. & Garcia-Blanco, S. (1985). Tetrahedron, 41, 3813-3823.]); Okabe & Adachi (1998[Okabe, N. & Adachi, Y. (1998). Acta Cryst. C54, 386-387.]); Merck (1973[Merck (1973). French Patent No. 2163554.]). For N-atom hybridization, see: Beddoes et al. (1986[Beddoes, R. L., Dalton, L., Joule, T. A., Mills, O. S., Street, J. D. & Watt, C. I. F. (1986). J. Chem. Soc. Perkin Trans. 2, pp. 787-797.]). For a related structure, see: Paramasivam et al. (2012[Paramasivam, S., Bhaskar, G., Seshadri, P. R. & Perumal, P. T. (2012). Acta Cryst. E68, o683-o684.]). For graph-set notation 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
  • C28H24ClNO3

  • Mr = 457.93

  • Monoclinic, P 21 /n

  • a = 8.7126 (3) Å

  • b = 19.1311 (6) Å

  • c = 13.9338 (4) Å

  • [beta] = 93.198 (2)°

  • V = 2318.89 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.20 mm-1

  • T = 298 K

  • 0.20 × 0.20 × 0.20 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • 22253 measured reflections

  • 5782 independent reflections

  • 4060 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.145

  • S = 1.03

  • 5782 reflections

  • 298 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.39 e Å-3

  • [Delta][rho]min = -0.46 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C8-H8...O2 0.93 2.26 2.850 (2) 121
C20-H20...O1i 0.93 2.52 3.374 (2) 152
Symmetry code: (i) -x, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). 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: ORTEP-3 for Windowa (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97, PLATON and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KP2444 ).


Acknowledgements

The authors acknowledge the Technology Business Incubator (TBI), CAS in Crystallography, University of Madras, Chennai 600 025, India, for the data collection.

References

Beddoes, R. L., Dalton, L., Joule, T. A., Mills, O. S., Street, J. D. & Watt, C. I. F. (1986). J. Chem. Soc. Perkin Trans. 2, pp. 787-797.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Ho, C. Y., Haegman, W. E. & Perisco, F. (1986). J. Med. Chem. 29, 118-121.
Joshi, K. C. & Chand, P. (1982). Pharmazie, 37, 1-12.  [ChemPort] [PubMed]
Merck (1973). French Patent No. 2163554.
Okabe, N. & Adachi, Y. (1998). Acta Cryst. C54, 386-387.  [CSD] [CrossRef] [details]
Olgen, S. & Coban, T. (2003). Biol. Pharm. Bull. 26, 736-738.  [CrossRef] [PubMed]
Paramasivam, S., Bhaskar, G., Seshadri, P. R. & Perumal, P. T. (2012). Acta Cryst. E68, o683-o684.  [CrossRef] [ChemPort] [details]
Rodriguez, J. G., Temprano, F., Esteban-Calderon, C., Martinez-Ripoll, M. & Garcia-Blanco, S. (1985). Tetrahedron, 41, 3813-3823.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o314-o315   [ doi:10.1107/S1600536813002456 ]

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