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Volume 70 
Part 5 
Page o540  
May 2014  

Received 12 December 2013
Accepted 30 March 2014
Online 12 April 2014

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.039
wR = 0.111
Data-to-parameter ratio = 15.5
Details
Open access

Methyl 1-ethyl-3'-[hy­droxy(naphthalen-1-yl)meth­yl]-1'-methyl-2-oxo­spiro­[indo­line-3,2'-pyrrolidine]-3'-carboxyl­ate

aDepartment of Life Sciences and Chemistry, Roskilde University, DK-4000 Roskilde, Denmark,bDepartment of Chemistry, Technical University of Denmark, 2800 Kgs. Lyngby, Denmark,cDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, and dDepartment of Physics, Presidency College, Chennai 600 005, India
Correspondence e-mail: vinothdlsc@gmail.com

In the title compound, C27H28N2O4, the pyrrolidine ring adopts a twist conformation. The plane of the indole ring is almost perpendicular to that of the pyrrolidine ring, making a dihedral angle of 88.50 (6)°. The planes of the naphthyl ring system and the pyrrolidine ring are tilted by an angle of 55.86 (5)°. The mol­ecular conformation is stabilized by intra­molecular O-H...O and O-H...N hydrogen bonds.

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.]); For uses of pyrrolidine derivative, see: Amal Raj et al. (2003[Amal Raj, A., Raghunathan, R., Sridevi Kumari, M. R. & Raman, N. (2003). Bioorg. Med. Chem. 11, 407-409.]); For conformation studies, see: Nardelli (1983[Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.]).

[Scheme 1]

Experimental

Crystal data
  • C27H28N2O4

  • Mr = 444.51

  • Orthorhombic, P b c a

  • a = 16.7802 (3) Å

  • b = 14.6690 (3) Å

  • c = 18.4735 (4) Å

  • V = 4547.23 (16) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.25 × 0.20 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.979, Tmax = 0.983

  • 44640 measured reflections

  • 4636 independent reflections

  • 3429 reflections with I > 2[sigma](I)

  • Rint = 0.041

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.111

  • S = 1.02

  • 4636 reflections

  • 299 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.14 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O4 0.82 2.37 2.9121 (16) 124
O1-H1...N1 0.82 2.39 2.9439 (17) 126

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supporting information for this paper is available from the IUCr electronic archives (Reference: BT6950 ).


References

Amal Raj, A., Raghunathan, R., Sridevi Kumari, M. R. & Raman, N. (2003). Bioorg. Med. Chem. 11, 407-409.  [PubMed]
Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.  [CrossRef] [IUCr Journals]
Pradhan, R., Patra, M., Behera, A. K. & Behera, R. K. (2006). Tetrahedron, 62, 779-828.  [Web of Science] [CrossRef] [ChemPort]
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]


Acta Cryst (2014). E70, o540  [ doi:10.1107/S1600536814007065 ]

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