Received 9 March 2013
The title compound, C23H21ClN4, contains two molecules (A and B) in the asymmetric unit, which are related to one another by a pseudo-inversion center. The non-aromatic pyrrolidine ring in each independent molecule adopts a half-chair conformation; the ring puckering parameters are = 0.407 (3) Å and = 270.5 (4)°, and the pseudo-rotation parameters are = 72.5 (3)° and = 42.2 (2)° for an N-C bond of molecule A, and the corresponding values are 0.415 (3) Å, 271.6 (4)°, 73.6 (3)° and 42.6 (2)° for molecule B. The dihedral angles between the central fused-ring system and the substituted chlorophenyl and methylphenyl rings are 66.35 and 45.59°, respectively, for molecule A, and 64.51 and 41.89° for molecule B. The geometry of all four intramolecular C-H interactions are of type III. - interactions involving the centroids of symmetry-related pyrrole rings of molecule B are 4.390 Å, contributing further to the stability of the molecule.
For background to and the biological activity of pyrrolo[2,3-d]pyrimidines, see: Chadwick (1990); Hulzenlaub et al. (1972); Ohgi et al. (1979); Smith et al. (1972). For our crystallographic investigations of heterocyclic compounds, see: Patel et al. (2007, 2012). For C-H interactions, see: Malone et al. (1997). For puckering parameters, see: Cremer & Pople (1975).
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GG2114 ).
The authors are thankful to Department of Physics, SPU, for providing the financial support to carry out this work and to Dr Babu Varghese of RSIC, IIT Madras, for helping us with the data collection. RDM is thankful to the UGC, New Delhi, for the UGC teacher fellowship under the FIP scheme and to Gujarat Arts and Science College, Ahmedabad, for allowing the research work to be carried out under the FIP scheme.
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