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

Abdulrahman I Almansour; Raju Suresh Kumar; Natarajan Arumugam; Hasnah Osman; J Suresh

doi:10.1107/S160053681204648X

. 2012 Nov 17;68(Pt 12):o3375. doi: 10.1107/S160053681204648X

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, J Suresh ^c,^*

PMCID: PMC3588971 PMID: 23476207

Abstract

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 ▶). 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,
a = 14.0679 (2) Å
b = 7.7245 (1) Å
c = 26.9686 (3) Å
β = 92.596 (1)°
V = 2927.60 (7) Å³
Z = 4
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.047

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.137
S = 1.02
8777 reflections
404 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.27 e Å⁻³

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 Material

Click here for additional data file.^{(30.4KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681204648X/pk2453sup1.cif

e-68-o3375-sup1.cif^{(30.4KB, cif)}

Click here for additional data file.^{(429.3KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681204648X/pk2453Isup2.hkl

e-68-o3375-Isup2.hkl^{(429.3KB, hkl)}

Click here for additional data file.^{(11.8KB, cml)}

Supplementary material file. DOI: 10.1107/S160053681204648X/pk2453Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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)

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

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

supplementary crystallographic information

Comment

The pyrrolidine ring system has been the subject of research for more than three decades. Many natural and synthetic compounds with pyrrolidine moieties have received much attention because of their remarkable biological properties (Shorvon, 2001; Watson et al., 2001; Asano et al., 2000; Winchester et al., 1992). Recognizing the importance of such compounds in drug discovery and as a part of our ongoing research in the construction of novel heterocycles, has prompted us to investigate the 1,3-dipolar cycloaddition of bisarylmethylidene pyridinones with azomethine ylide generated in situ from acenaphthenequinone and proline, we and report the crystal structure of the resulting pyrrolidine cyclo-adduct in this paper.

In the title compound,C₄₀H₃₄N₂ O₂, the piperidine ring (N1/C1—C4/C9) adopts a half-chair conformation [Q = 0.6188 (2) Å, θ = 142.52 (2)°, φ = 123.6 (2)°; Cremer & Pople, 1975] which is in close agreement with those of the other related structures (Kumar et al. 2010; Kumar et al.2011; Kumar et al. 2012). The two fused pyrrolidine rings with atom sequences (N1/C4/C7—C9) and (N2/C4—C7), adopt a twisted envelope conformation (C9 atom as the flap) and an envelope conformation (C5 atom as the flap) respectively. The puckering parameters are Q = 0.4648 (15) Å, φ =325.20 (19)° for the N1/C4/C7—C9) pyrrolidine ring and Q = 0.3918 (16) Å, φ = 77.9 (2)° for the (N2/C4—C7) pyrrolidine ring. In the structure, the aryl ring C22—C27 is not coplanar with the mean plane of the piperidone ring [torsion angle C1—C2—C21—C22 is 5.77 (3)] °, which is due to non-bonded interactions between one of the ortho H atoms in the aryl ring and the equatorial H atom at the 2-position of the piperidone ring (H12A/H1A or H1B).

The molecular structure features weak intra-molecular N—H···O and C—H···O interactions. Intermolecular O2—H2···O1 bonds form an infinite one-dimensional chain parallel to the b axis, in a C₁¹(7) motif (Bernstein et al., 1995).

Experimental

A mixture of 3,5-bis[(E)-(2-methylphenyl)methylidene]tetrahydro-4(1H)-pyridinone (1 mmol), acenaphthenequinone (1 mmol), and phenylglycine (1 mmol) were dissolved in methanol (5 ml) and refluxed in a water bath for 1 h. After completion of the reaction as evident from TLC, the mixture was poured into water (50 ml). The precipitated solid was filtered and washed with water to obtain the product which was further purified by recrystallization from ethyl acetate. Yield 89%, melting point 212–213°C