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

Paramasivam, S.; Purushothaman, S.; Seshadri, P.R.; Raghunathan, R.

doi:10.1107/S1600536813002456

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 (C-C) = 0.003 Å
R = 0.049
wR = 0.145
Data-to-parameter ratio = 19.4
Details

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

S. Paramasivam,^a Santhanagopalan Purushothaman,^b P. R. Seshadri ^a ^* and Raghavachary Raghunathan ^b

^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-HO interaction. In the crystal, pairs of C-HO 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); Ho et al. (1986); Joshi & Chand (1982); Rodriguez et al. (1985); Okabe & Adachi (1998); Merck (1973). For N-atom hybridization, see: Beddoes et al. (1986). For a related structure, see: Paramasivam et al. (2012). For graph-set notation see: Bernstein et al. (1995).

Experimental

Crystal data

C₂₈H₂₄ClNO₃
M_r = 457.93
Monoclinic, P 2₁ /n
a = 8.7126 (3) Å
b = 19.1311 (6) Å
c = 13.9338 (4) Å
= 93.198 (2)°
V = 2318.89 (13) Å³
Z = 4
Mo K radiation
= 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(I)
R_int = 0.026

Refinement

R[F² > 2(F²)] = 0.049
wR(F²) = 0.145
S = 1.03
5782 reflections
298 parameters
H-atom parameters constrained
_max = 0.39 e Å^-3
_min = -0.46 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C8-H8O2	0.93	2.26	2.850 (2)	121
C20-H20O1ⁱ	0.93	2.52	3.374 (2)	152
Symmetry code: (i) -x, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windowa (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97, PLATON and publCIF (Westrip, 2010).

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.
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
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.
Merck (1973). French Patent No. 2163554.
Okabe, N. & Adachi, Y. (1998). Acta Cryst. C54, 386-387.
Olgen, S. & Coban, T. (2003). Biol. Pharm. Bull. 26, 736-738.
Paramasivam, S., Bhaskar, G., Seshadri, P. R. & Perumal, P. T. (2012). Acta Cryst. E68, o683-o684.
Rodriguez, J. G., Temprano, F., Esteban-Calderon, C., Martinez-Ripoll, M. & Garcia-Blanco, S. (1985). Tetrahedron, 41, 3813-3823.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.