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Volume 69 
Part 8 
Pages o1286-o1287  
August 2013  

Received 9 March 2013
Accepted 10 July 2013
Online 20 July 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.042
wR = 0.125
Data-to-parameter ratio = 13.5
Details
Open access

5-(4-Chlorophenyl)-7-(4-methylphenyl)-4-(pyrrolidin-1-yl)-7H-pyrrolo[2,3-d]pyrimidine

aDepartment of Physics, Sardar Patel University, Vallabh Vidya Nagar, Gujarat 388 120, India, and bOrganic Syntheses Laboratory, M. G. Science Institute, Navarangpura, Ahmedabad 380 009, India
Correspondence e-mail: u_h_patel@yahoo.com

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 [theta] = 0.407 (3) Å and [varphi] = 270.5 (4)°, and the pseudo-rotation parameters are [rho] = 72.5 (3)° and [tau] = 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...[pi] interactions are of type III. [pi]-[pi] interactions involving the centroids of symmetry-related pyrrole rings of molecule B are 4.390 Å, contributing further to the stability of the molecule.

Related literature

For background to and the biological activity of pyrrolo[2,3-d]pyrimidines, see: Chadwick (1990[Chadwick, D. J. (1990). The Chemistry of Heterocyclic Compounds, Vol. 48, edited by R. A. Jones, pp. 1-104. New York: Willey & Sons.]); Hulzenlaub et al. (1972[Hulzenlaub, W., Tolman, R. L. & Robins, R. K. (1972). J. Med. Chem. 15, 879-883.]); Ohgi et al. (1979[Ohgi, T., Kondo, T. & Goto, T. (1979). J. Am. Chem. Soc. 101, 3629-3633.]); Smith et al. (1972[Smith, C. W., Sidwell, R. W., Robins, R. K. & Tolman, R. L. (1972). J. Med. Chem. 15, 883-887.]). For our crystallographic investigations of heterocyclic compounds, see: Patel et al. (2007[Patel, U. H., Patel, P. D. & Thakker, N. (2007). Acta Cryst. C63, o337-o339.], 2012[Patel, U. H., Gandhi, S. A., Barot, V. M. & Patel, M. C. (2012). Acta Cryst. E68, o2926-o2927.]). For C-H...[pi] interactions, see: Malone et al. (1997[Malone, J. F., Murray, C. M., Charlton, M. H., Docherty, R. & Lavery, A. J. (1997). J. Chem. Soc. Faraday Trans. 93, 3429-3436.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C23H21ClN4

  • Mr = 388.72

  • Triclinic, [P \overline 1]

  • a = 8.967 (3) Å

  • b = 15.367 (5) Å

  • c = 15.960 (2) Å

  • [alpha] = 69.210 (17)°

  • [beta] = 75.653 (16)°

  • [gamma] = 76.52 (3)°

  • V = 1966.2 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.21 mm-1

  • T = 293 K

  • 0.3 × 0.2 × 0.2 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.951, Tmax = 0.959

  • 7458 measured reflections

  • 6864 independent reflections

  • 3569 reflections with I > 2[sigma](I)

  • Rint = 0.027

  • 2 standard reflections every 1 min intensity decay: none

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.125

  • S = 1.01

  • 6864 reflections

  • 507 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3 and Cg4 are the centroids of the N6/C5/C4/C9/N8/C7, N34/C33/C32/C37/N36/C35, C17-C22 and C45-C50 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C18-H18...Cg1i 0.93 2.68 3.483 (3) 144
C46-H46...Cg2ii 0.93 2.73 3.549 (3) 147
C25-H251...Cg3 0.97 2.79 3.462 (3) 127
C53-H531...Cg4 0.97 2.84 3.506 (3) 127
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x, -y+1, -z+2.

Data collection: CAD-4 Software (Enraf-Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; 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: 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: GG2114 ).


Acknowledgements

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.

References

Chadwick, D. J. (1990). The Chemistry of Heterocyclic Compounds, Vol. 48, edited by R. A. Jones, pp. 1-104. New York: Willey & Sons.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Hulzenlaub, W., Tolman, R. L. & Robins, R. K. (1972). J. Med. Chem. 15, 879-883.  [PubMed] [Web of Science]
Malone, J. F., Murray, C. M., Charlton, M. H., Docherty, R. & Lavery, A. J. (1997). J. Chem. Soc. Faraday Trans. 93, 3429-3436.  [CrossRef] [ChemPort]
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [IUCr Journals]
Ohgi, T., Kondo, T. & Goto, T. (1979). J. Am. Chem. Soc. 101, 3629-3633.  [CrossRef] [ChemPort] [Web of Science]
Patel, U. H., Gandhi, S. A., Barot, V. M. & Patel, M. C. (2012). Acta Cryst. E68, o2926-o2927.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Patel, U. H., Patel, P. D. & Thakker, N. (2007). Acta Cryst. C63, o337-o339.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Smith, C. W., Sidwell, R. W., Robins, R. K. & Tolman, R. L. (1972). J. Med. Chem. 15, 883-887.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1286-o1287   [ doi:10.1107/S1600536813019168 ]

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