[Journal logo]

Volume 68 
Part 12 
Page o3375  
December 2012  

Received 24 October 2012
Accepted 10 November 2012
Online 17 November 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.054
wR = 0.137
Data-to-parameter ratio = 21.7
Details
Open access

2-Hydroxy-5-[(E)-2-methylbenzylidene]-8-(2-methylphenyl)-9-phenyl-3,10-diazahexacyclo[10.7.1.13,7.02,11.07,11.016,20]henicosa-1(20),12,14,16,18-pentaen-6-one

aDepartment of Chemistry, College of Sciences, King Saud University, PO Box 2455, Riyadh 11451, Saudi Arabia,bSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and cDepartment of Physics, The Madura College, Madurai 625 011, India
Correspondence e-mail: ambujasureshj@yahoo.com

In the title compound, C40H34N2O2, the central piperidine ring adopts a half-chair conformation and the fused pyrrolidine rings adopt twisted envelope (with the C atom bearing the methylphenyl ring as the flap atom) and envelope (with the C atom bound to the N atom, common to the pyridinone and pyrrolidine rings being the flap atom) conformations. The molecular structure features weak intramolecular N-H...O and C-H...O interactions. In the crystal, O-H...O hydrogen bonds generate a C(7) chain along the b-axis direction. C-H...O interactions also occur.

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For similar structures, see: Kumar et al. (2010[Kumar, R. S., Osman, H., Abdul Rahim, A. S., Hemamalini, M. & Fun, H.-K. (2010). Acta Cryst. E66, o3045.], 2011[Kumar, R. S., Osman, H., Rahim, A. S. A., Hemamalini, M. & Fun, H.-K. (2011). Acta Cryst. E67, o2881-o2882.], 2012[Kumar, R. S., Osman, H., Almansour, A. I., Arshad, S. & Razak, I. A. (2012). Acta Cryst. E68, o2094-o2095.]). For the importance of pyrrolidine, see: Asano et al. (2000[Asano, N., Nash, R. J., Molyneux, R. J. & Fleet, G. W. J. (2000). Tetrahedron Asymmetry, 11, 1645-1680.]); Shorvon (2001[Shorvon, S. (2001). Lancet, 358, 1885-92.]); Watson et al. (2001[Watson, A. A., Fleet, G. W. J., Asano, N., Molyneux, R. J. & Nash, R. J. (2001). Phytochemistry, 56, 265-295.]); Winchester & Fleet (1992[Winchester, B. & Fleet, G. W. J. (1992). Glycobiology, 2, 199-210.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C40H34N2O2

  • Mr = 574.69

  • Monoclinic, P 21 /c

  • a = 14.0679 (2) Å

  • b = 7.7245 (1) Å

  • c = 26.9686 (3) Å

  • [beta] = 92.596 (1)°

  • V = 2927.60 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 293 K

  • 0.21 × 0.15 × 0.13 mm

Data collection
  • Bruker Kappa APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.973, Tmax = 0.978

  • 33520 measured reflections

  • 8777 independent reflections

  • 6575 reflections with I > 2[sigma](I)

  • Rint = 0.047

Refinement
  • R[F2 > 2[sigma](F2)] = 0.054

  • wR(F2) = 0.137

  • S = 1.02

  • 8777 reflections

  • 404 parameters

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

  • [Delta][rho]max = 0.48 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2...O1i 0.82 2.02 2.7828 (15) 155
C1-H1A...O2ii 0.97 2.46 3.3040 (16) 145
C57-H57B...O1 0.96 2.59 3.3859 (18) 141
N2-H2A...O2 0.92 (2) 2.27 (2) 2.8016 (18) 117 (2)
Symmetry codes: (i) x, y-1, z; (ii) [-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: PK2453 ).


Acknowledgements

This project was supported by the Research Center, College of Science, King Saud University.

References

Asano, N., Nash, R. J., Molyneux, R. J. & Fleet, G. W. J. (2000). Tetrahedron Asymmetry, 11, 1645-1680.  [ISI] [CrossRef] [ChemPort]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
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] [ISI]
Kumar, R. S., Osman, H., Abdul Rahim, A. S., Hemamalini, M. & Fun, H.-K. (2010). Acta Cryst. E66, o3045.  [CSD] [CrossRef] [details]
Kumar, R. S., Osman, H., Rahim, A. S. A., Hemamalini, M. & Fun, H.-K. (2011). Acta Cryst. E67, o2881-o2882.  [CSD] [CrossRef] [details]
Kumar, R. S., Osman, H., Almansour, A. I., Arshad, S. & Razak, I. A. (2012). Acta Cryst. E68, o2094-o2095.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shorvon, S. (2001). Lancet, 358, 1885-92.  [ISI] [CrossRef] [PubMed] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Watson, A. A., Fleet, G. W. J., Asano, N., Molyneux, R. J. & Nash, R. J. (2001). Phytochemistry, 56, 265-295.  [ISI] [CrossRef] [PubMed] [ChemPort]
Winchester, B. & Fleet, G. W. J. (1992). Glycobiology, 2, 199-210.  [CrossRef] [PubMed] [ChemPort] [ISI]


Acta Cryst (2012). E68, o3375  [ doi:10.1107/S160053681204648X ]

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.