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Volume 69 
Part 10 
Page o1581  
October 2013  

Received 7 September 2013
Accepted 15 September 2013
Online 21 September 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.053
wR = 0.161
Data-to-parameter ratio = 23.5
Details
Open access

14a-Hydroxy-12-methyl-10-(4-methylphenyl)-8,9,9a,10,12,13,14,14a-octahydro-10a,14-methano-5H-indeno[2',1':4,5]azepino[3,4-b]pyrrolizine-5,15(7H,11H)-dione

aDepartment of Physics, The Madura College, Madurai 625 011, India,bDepartment of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, India, and cDepartment of Food Science and Technology, University of Ruhuna, Mapalana, Kamburupitiya 81100, Sri Lanka
Correspondence e-mail: plakshmannilantha@ymail.com

In the title compound, C27H28N2O3, each of the pyrrolidine rings adopts a twisted conformation, as does the cyclopentane ring. The indane ring has an r.m.s deviation of 0.0693 Å. The dihedral angle between the mean plane of the pyrrolizine ring and indane system is 82.58 (1)°. The piperidine ring has the methyl substituent in an equatorial position and adopts a twisted chair conformation. The molecular structure is stabilized by a weak intramolecular O-H...N interaction.

Related literature

For the importance of pyrrazole derivatives, see: Mahajan et al. (1991[Mahajan, R. N., Havaldar, F. H. & Fernandes, P. S. (1991). J. Indian Chem. Soc. 68, 245-249.]); Katayama & Oshiyama (1997[Katayama, H. & Oshiyama, T. (1997). Can. J. Chem. 75, 913-919.]); Baraldi et al. (1998[Baraldi, P. G., Manfredini, S., Romagnoli, R., Stevanato, L., Zaid, A. N. & Manservigi, R. (1998). Nucleosides Nucleotides, 17, 2165-2171.]). For additional conformation analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C27H28N2O3

  • Mr = 428.51

  • Monoclinic, P 21 /c

  • a = 16.8684 (6) Å

  • b = 8.3754 (3) Å

  • c = 15.9930 (6) Å

  • [beta] = 96.658 (1)°

  • V = 2244.25 (14) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 293 K

  • 0.21 × 0.19 × 0.18 mm

Data collection
  • Bruker Kappa APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.]) Tmin = 0.967, Tmax = 0.974

  • 28459 measured reflections

  • 6850 independent reflections

  • 4500 reflections with I > 2[sigma](I)

  • Rint = 0.030

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

  • wR(F2) = 0.161

  • S = 1.02

  • 6850 reflections

  • 291 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...N2 0.82 2.13 2.6497 (16) 121
Symmetry code: (i) [-x, y-{\script{1\over 2}}, -z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5254 ).


Acknowledgements

JS and RAN thank the management of Madura College for their encouragement and support. RRK thanks the DST, New Delhi, for funds under the fast-track scheme (No. SR/FT/CS-073/2009).

References

Baraldi, P. G., Manfredini, S., Romagnoli, R., Stevanato, L., Zaid, A. N. & Manservigi, R. (1998). Nucleosides Nucleotides, 17, 2165-2171.  [CrossRef] [ChemPort]
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Katayama, H. & Oshiyama, T. (1997). Can. J. Chem. 75, 913-919.  [CrossRef] [ChemPort] [Web of Science]
Mahajan, R. N., Havaldar, F. H. & Fernandes, P. S. (1991). J. Indian Chem. Soc. 68, 245-249.  [ChemPort]
Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.
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 (2013). E69, o1581  [ doi:10.1107/S1600536813025592 ]

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