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Volume 69 
Part 7 
Pages o1062-o1063  
July 2013  

Received 7 May 2013
Accepted 1 June 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.053
wR = 0.161
Data-to-parameter ratio = 19.4
Details
Open access

Ethyl 8''-chloro-1'-methyl-2,12''-dioxo-12''H-dispiro[indoline-3,2'-pyrrolidine- 3',6''-indolo[2,1-b]quinazoline]-4'-carboxylate

aDepartment of Physics, S.M.K. Fomra Institute of Technology, Thaiyur, Chennai 603 103, India,bOrganic Chemistry Division, CSIR Central Leather Research Institute, Adyar, Chennai 600 020, India, and cDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India
Correspondence e-mail: a_sp59@yahoo.in

In the title compound, C29H23ClN4O4, the quinazoline-indole system and the indolin-2-one system are each essentially planar, with maximum deviations from their mean planes of 0.150 (2) and 0.072 (2) Å, respectively. The central pyrrolidine ring adopts a twisted conformation on the C-C bond involving the spiro C atoms. Its mean plane forms dihedral angles of 83.37 (9) and 86.56 (8)°, respectively, with the indole rings of the indolin-2-one and quinazoline-indole systems. In the crystal, molecules are linked via pairs of N-H...O hydrogen bonds, forming inversion dimers. The dimers are linked via C-H...O hydrogen bonds, forming chains propagating along [001].

Related literature

For quinazoline structures, see: Li & Feng (2009[Li, M.-J. & Feng, C.-J. (2009). Acta Cryst. E65, o2145.]); Li et al. (2010[Li, D.-L., Wu, Y., Wang, Q., He, G. & Yu, L.-T. (2010). Acta Cryst. E66, o447.]); Priya et al. (2011a[Priya, M. G. R., Srinivasan, T., Girija, K., Chandran, N. R. & Velmurugan, D. (2011a). Acta Cryst. E67, o2310.]). For the biological activity of quinazoline derivatives, see: Wolfe et al. (1990[Wolfe, J. F., Rathman, T. L., Sleevi, M. C., Campbell, J. S. A. & Greenwood, T. D. (1990). J. Med. Chem. 33, 161-166.]); Tereshima et al. (1995[Tereshima, K., Shimamura, H., Kawase, A., Tanaka, Y., Tanimura, T., Ishizuka, Y. & Sato, M. (1995). Chem. Pharm. Bull. 45, 2021-2023.]); Pandeya et al. (1999[Pandeya, S. N., Sriram, D., Nath, G. & Declera, E. (1999). Pharm. Acta Helv. 74, 11-17.]); Priya et al. (2011b[Priya, M. G. R., Zulykama, Y., Girija, K., Murugesh, S. & Perumal, P. T. (2011b). Indian J. Chem. Sect. B, 50, 98-102.]). For ring conformations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C29H23ClN4O4

  • Mr = 526.96

  • Triclinic, [P \overline 1]

  • a = 8.9341 (9) Å

  • b = 11.7697 (12) Å

  • c = 13.3828 (14) Å

  • [alpha] = 72.776 (5)°

  • [beta] = 89.574 (5)°

  • [gamma] = 74.995 (5)°

  • V = 1294.6 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.19 mm-1

  • T = 293 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker. (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, U. S. A.]) Tmin = 0.945, Tmax = 0.963

  • 16756 measured reflections

  • 6722 independent reflections

  • 5191 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.053

  • wR(F2) = 0.161

  • S = 1.04

  • 6722 reflections

  • 346 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.59 e Å-3

  • [Delta][rho]min = -0.50 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N4-H4...O4i 0.86 1.98 2.808 (2) 160
C20-H20C...O1ii 0.96 2.53 3.369 (6) 146
Symmetry codes: (i) -x+1, -y, -z; (ii) -x, -y, -z+1.

Data collection: APEX2 (Bruker, 2008[Bruker. (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, U. S. A.]); cell refinement: SAINT (Bruker, 2008[Bruker. (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, U. S. A.]); 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 Windows (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 and PLATON.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2600 ).


Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and BioPhysics, University of Madras, Chennai, India, for the data collection.

References

Bruker. (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, U. S. A.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Li, M.-J. & Feng, C.-J. (2009). Acta Cryst. E65, o2145.  [CSD] [CrossRef] [IUCr Journals]
Li, D.-L., Wu, Y., Wang, Q., He, G. & Yu, L.-T. (2010). Acta Cryst. E66, o447.  [CSD] [CrossRef] [IUCr Journals]
Pandeya, S. N., Sriram, D., Nath, G. & Declera, E. (1999). Pharm. Acta Helv. 74, 11-17.  [CrossRef] [PubMed] [ChemPort]
Priya, M. G. R., Srinivasan, T., Girija, K., Chandran, N. R. & Velmurugan, D. (2011a). Acta Cryst. E67, o2310.  [CSD] [CrossRef] [IUCr Journals]
Priya, M. G. R., Zulykama, Y., Girija, K., Murugesh, S. & Perumal, P. T. (2011b). Indian J. Chem. Sect. B, 50, 98-102.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Tereshima, K., Shimamura, H., Kawase, A., Tanaka, Y., Tanimura, T., Ishizuka, Y. & Sato, M. (1995). Chem. Pharm. Bull. 45, 2021-2023.
Wolfe, J. F., Rathman, T. L., Sleevi, M. C., Campbell, J. S. A. & Greenwood, T. D. (1990). J. Med. Chem. 33, 161-166.  [CrossRef] [ChemPort] [PubMed] [Web of Science]


Acta Cryst (2013). E69, o1062-o1063   [ doi:10.1107/S1600536813015146 ]

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