[Journal logo]

Volume 69 
Part 8 
Page o1269  
August 2013  

Received 8 June 2013
Accepted 11 July 2013
Online 17 July 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.044
wR = 0.125
Data-to-parameter ratio = 18.4
Details
Open access

Ethyl 1,4-bis(4-chlorophenyl)-2-methyl-1H-pyrrole-3-carboxylate

aDepartment of Studies in Chemistry, Manasagangotri, University of Mysore, Mysore 570 006, India,bDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India, and cSER-CAT, APS, Argonne National Laboratory, Argonne, IL 60439, USA
Correspondence e-mail: kmantelingu@yahoo.com

In the title molecule, C20H17Cl2NO2, the pyrrole moiety makes dihedral angles of 63.42 (11) and 70.43 (12)° with the chlorobenzene rings. The ethoxycarbonyl unit is present in a synperiplanar conformation with respect to the pyrrole ring, as indicated by the dihedral angle of 14.5 (3)°. In the crystal, molecules are linked into chains parallel to the a-axis direction by weak C-H...O hydrogen bonds.

Related literature

For the biological importance of pyrroles, see: Banwell et al. (2006[Banwell, M. G., Hamel, E., Hockless, D. C. R., Verdier-Pinard, P., Willis, A. C. & Wong, D. J. (2006). Bioorg. Med. Chem. 14, 4627-4638.]); Mohamed et al. (2009[Mohamed, M. S., El-Domany, R. A. & El-Hameed, R. H. A. (2009). Acta Pharm. 59, 145-158.]); Sosa et al. (2002[Sosa, A. C. B., Yakushijin, K. & Horne, D. A. (2002). J. Org. Chem. 67, 4498-4500.]).

[Scheme 1]

Experimental

Crystal data
  • C20H17Cl2NO2

  • Mr = 374.25

  • Triclinic, [P \overline 1]

  • a = 8.037 (2) Å

  • b = 9.797 (3) Å

  • c = 12.510 (4) Å

  • [alpha] = 72.774 (16)°

  • [beta] = 86.838 (16)°

  • [gamma] = 76.804 (16)°

  • V = 915.9 (5) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.37 mm-1

  • T = 296 K

  • 0.15 × 0.15 × 0.15 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2001[Sheldrick, G. M. (2001). SADABS, University of Göttingen, Germany.]) Tmin = 0.947, Tmax = 0.947

  • 15843 measured reflections

  • 4196 independent reflections

  • 2759 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.125

  • S = 1.03

  • 4196 reflections

  • 228 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2...O8i 0.93 2.58 3.453 (3) 157
C6-H6C...O8 0.96 2.42 3.041 (3) 122
Symmetry code: (i) x+1, y, z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). 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: FB2292 ).


Acknowledgements

C and KNN would like to thank the University of Mysore for awarding RFSMS fellowships [DV5/Physics/389/RFSMS/2009-2010/10.07.2012 and No. F4-1/2006(BSR)/7-131/2007, respectively].

References

Banwell, M. G., Hamel, E., Hockless, D. C. R., Verdier-Pinard, P., Willis, A. C. & Wong, D. J. (2006). Bioorg. Med. Chem. 14, 4627-4638.  [CrossRef] [PubMed] [ChemPort]
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Mohamed, M. S., El-Domany, R. A. & El-Hameed, R. H. A. (2009). Acta Pharm. 59, 145-158.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2001). SADABS, University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sosa, A. C. B., Yakushijin, K. & Horne, D. A. (2002). J. Org. Chem. 67, 4498-4500.  [CrossRef] [PubMed] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1269  [ doi:10.1107/S1600536813019247 ]

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.