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Volume 69 
Part 6 
Page o822  
June 2013  

Received 26 March 2013
Accepted 27 April 2013
Online 4 May 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.047
wR = 0.134
Data-to-parameter ratio = 15.4
Details
Open access

Ethyl 1''-benzyl-1'-methyl-2''-oxodispiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolidine-2',3''-indoline]-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, C36H30N4O3, the quinoxaline-indene system is roughly planar, with a maximum deviation from the mean plane of 0.218 Å for the C atom shared with the central pyrrolidine ring. This latter ring forms dihedral angles of 84.54 (7) and 83.91 (8)° with the quinoxaline-indene system and the indole ring, respectively. The central pyrrolidine ring has an envelope conformation with the N atom as the flap, while the pyrrolidine and five-membered rings of the indole group adopt twisted conformation and envelope (with the C atom bearing the quinoxaline-indene system as the flap) conformations, respectively. In the crystal, molecules are linked via weak C-H...N hydrogen bonds, forming a chain running along [100].

Related literature

For details of the synthesis, see: Azizian et al. (2005[Azizian, J., Mohammadizadeh, M. R., Karimi, N., Kazemizadeh, Z., Mohammadi, A. A. & Karimi, A. R. (2005). Heteroat. Chem. 16, 549-552.]). For uses of pyrrolidine and quinoxaline derivatives, see: Amal Raj et al. (2003[Amal Raj, A., Raghunathan, R., Sridevi Kumari, M. R. & Raman, N. (2003). Bioorg. Med. Chem. 11, 407-409.]); Zarranz et al. (2003[Zarranz, B., Jago, A., Aldana, I. & Monge, A. (2003). Bioorg. Med. Chem. 11, 2149-2156.]). For a related structure, see: Srinivasan et al. (2012[Srinivasan, T., Suhitha, S., Purushothaman, S., Raghunathan, R. & Velmurugan, D. (2012). Acta Cryst. E68, o2469.]). 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
  • C36H30N4O3

  • Mr = 566.64

  • Triclinic, [P \overline 1]

  • a = 11.1927 (2) Å

  • b = 11.4535 (3) Å

  • c = 12.1206 (3) Å

  • [alpha] = 87.637 (2)°

  • [beta] = 86.048 (1)°

  • [gamma] = 70.564 (2)°

  • V = 1461.50 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 293 K

  • 0.35 × 0.30 × 0.25 mm

Data collection
  • Bruker APEXII CCD area detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.971, Tmax = 0.980

  • 21785 measured reflections

  • 5987 independent reflections

  • 4956 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.134

  • S = 1.04

  • 5987 reflections

  • 388 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.36 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C27-H27...N4i 0.93 2.60 3.446 (2) 152
Symmetry code: (i) x-1, y, z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2503 ).


Acknowledgements

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

References

Amal Raj, A., Raghunathan, R., Sridevi Kumari, M. R. & Raman, N. (2003). Bioorg. Med. Chem. 11, 407-409.  [PubMed]
Azizian, J., Mohammadizadeh, M. R., Karimi, N., Kazemizadeh, Z., Mohammadi, A. A. & Karimi, A. R. (2005). Heteroat. Chem. 16, 549-552.  [ISI] [CrossRef] [ChemPort]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Srinivasan, T., Suhitha, S., Purushothaman, S., Raghunathan, R. & Velmurugan, D. (2012). Acta Cryst. E68, o2469.  [CSD] [CrossRef] [details]
Zarranz, B., Jago, A., Aldana, I. & Monge, A. (2003). Bioorg. Med. Chem. 11, 2149-2156.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o822  [ doi:10.1107/S1600536813011525 ]

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