[Journal logo]

Volume 69 
Part 6 
Pages o854-o855  
June 2013  

Received 26 March 2013
Accepted 27 April 2013
Online 11 May 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.040
wR = 0.114
Data-to-parameter ratio = 12.8
Details
Open access

Ethyl 1''-benzyl-2''-oxo-2',3',5',6',7',7a'-hexahydro-1'H-dispiro[indeno[1,2-b]quinoxaline-11,2'-pyrrolizine-3',3''-indoline]-1'-carboxylate monohydrate

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, C38H32N4O3·H2O, the quinoxaline-indene and pyrrolizine systems are essentially planar, with maximum deviations from their mean planes of 0.162 and 0.563 Å, respectively. The pyrrolizine ring forms dihedral angles of 88.53 (5) and 89.95 (8)° with the quinoxaline-indene system and the indoline ring, respectively. The central pyrrolidine ring has an envelope conformation with the C atom bearing the quinoxaline-indene system as the flap. The pyrrolidine ring of the indole system adopts an envelope conformation with the C atom bonded to the pyrrolizine ring N atom as the flap. The five-membered ring attached to the central pyrolidine ring adopts a twisted conformation. In the crystal, O-H...N and O-H...O hydrogen bonds between water molecules and pyrrolizine N and carbonyl O atoms together with C-H...O interactions result in chains along [100].

Related literature

For general background to spiro compounds and their biological activity, see: Pradhan et al. (2006[Pradhan, R., Patra, M., Behera, A. K. & Behera, R. K. (2006). Tetrahedron, 62, 779-828.]); Saeedi et al. (2010[Saeedi, M., Heravi, M. M., Beheshtiha, Y. S. & Oskooie, H. A. (2010). Tetrahedron, 66, 5345-5348.]); Dandia et al. (2011[Dandia, A., Singh, R., Bhaskarana, S. & Samant, S. D. (2011). Green Chem. 13, 1852-1859.]); He et al. (2003[He, W., Meyers, M. R., Hanney, B., Sapada, A., Blider, G., Galzeinski, H., Amin, D., Needle, S., Page, K., Jayyosi, Z. & Perrone, H. (2003). Bioorg. Med. Chem. Lett. 13, 3097-3100.]). 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.]). 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.]).

[Scheme 1]

Experimental

Crystal data
  • C38H32N4O3·H2O

  • Mr = 610.69

  • Triclinic, [P \overline 1]

  • a = 11.0527 (3) Å

  • b = 11.5834 (3) Å

  • c = 12.2015 (3) Å

  • [alpha] = 97.370 (1)°

  • [beta] = 92.037 (1)°

  • [gamma] = 96.810 (1)°

  • V = 1536.25 (7) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.25 × 0.22 × 0.19 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 = 0.979, Tmax = 0.984

  • 21165 measured reflections

  • 5410 independent reflections

  • 4751 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.114

  • S = 1.02

  • 5410 reflections

  • 422 parameters

  • 3 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O4-H4A...N2 0.99 (2) 2.03 (2) 2.996 (2) 164 (2)
O4-H4B...O1i 0.99 (2) 2.31 (2) 3.222 (2) 154 (2)
C2-H2...O1ii 0.93 2.50 3.393 (2) 162
C24-H24A...O4iii 0.97 2.56 3.495 (3) 163
Symmetry codes: (i) x+1, y, z; (ii) -x, -y+1, -z+2; (iii) -x+1, -y+1, -z+2.

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: BX2437 ).


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]
Dandia, A., Singh, R., Bhaskarana, S. & Samant, S. D. (2011). Green Chem. 13, 1852-1859.  [ISI] [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
He, W., Meyers, M. R., Hanney, B., Sapada, A., Blider, G., Galzeinski, H., Amin, D., Needle, S., Page, K., Jayyosi, Z. & Perrone, H. (2003). Bioorg. Med. Chem. Lett. 13, 3097-3100.  [CrossRef] [PubMed] [ChemPort]
Pradhan, R., Patra, M., Behera, A. K. & Behera, R. K. (2006). Tetrahedron, 62, 779-828.  [ISI] [CrossRef] [ChemPort]
Saeedi, M., Heravi, M. M., Beheshtiha, Y. S. & Oskooie, H. A. (2010). Tetrahedron, 66, 5345-5348.  [ISI] [CrossRef] [ChemPort]
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, o854-o855   [ doi:10.1107/S1600536813011537 ]

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.