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

Almansour, A.I.; Kumar, R.S.; Arumugam, N.; Osman, H.; Suresh, J.

doi:10.1107/S160053681204648X

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 (C-C) = 0.002 Å
R = 0.054
wR = 0.137
Data-to-parameter ratio = 21.7
Details

2-Hydroxy-5-[(E)-2-methylbenzylidene]-8-(2-methylphenyl)-9-phenyl-3,10-diazahexacyclo[10.7.1.1^3,7.0^2,11.0^7,11.0^16,20]henicosa-1(20),12,14,16,18-pentaen-6-one

Abdulrahman I. Almansour,^a Raju Suresh Kumar,^a Natarajan Arumugam,^a Hasnah Osman ^b and J. Suresh ^c ^*

^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-HO and C-HO interactions. In the crystal, O-HO hydrogen bonds generate a C(7) chain along the b-axis direction. C-HO interactions also occur.

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995). For similar structures, see: Kumar et al. (2010, 2011, 2012). For the importance of pyrrolidine, see: Asano et al. (2000); Shorvon (2001); Watson et al. (2001); Winchester & Fleet (1992). For puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₄₀H₃₄N₂O₂
M_r = 574.69
Monoclinic, P 2₁ /c
a = 14.0679 (2) Å
b = 7.7245 (1) Å
c = 26.9686 (3) Å
= 92.596 (1)°
V = 2927.60 (7) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.973, T_max = 0.978
33520 measured reflections
8777 independent reflections
6575 reflections with I > 2(I)
R_int = 0.047

Refinement

R[F² > 2(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
_max = 0.48 e Å^-3
_min = -0.27 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2O1ⁱ	0.82	2.02	2.7828 (15)	155
C1-H1AO2ⁱⁱ	0.97	2.46	3.3040 (16)	145
C57-H57BO1	0.96	2.59	3.3859 (18)	141
N2-H2AO2	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); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); 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.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Kumar, R. S., Osman, H., Abdul Rahim, A. S., Hemamalini, M. & Fun, H.-K. (2010). Acta Cryst. E66, o3045.
Kumar, R. S., Osman, H., Rahim, A. S. A., Hemamalini, M. & Fun, H.-K. (2011). Acta Cryst. E67, o2881-o2882.
Kumar, R. S., Osman, H., Almansour, A. I., Arshad, S. & Razak, I. A. (2012). Acta Cryst. E68, o2094-o2095.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shorvon, S. (2001). Lancet, 358, 1885-92.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Watson, A. A., Fleet, G. W. J., Asano, N., Molyneux, R. J. & Nash, R. J. (2001). Phytochemistry, 56, 265-295.
Winchester, B. & Fleet, G. W. J. (1992). Glycobiology, 2, 199-210.