r-2,c-6-Bis(2-methoxy­phen­yl)-t-3,t-5-dimethyl­piperidin-4-one acetic acid solvate

G Aridoss; S Sundaramoorthy; D Velmurugan; K S Park; Y T Jeong

doi:10.1107/S1600536810017721

. 2010 May 22;66(Pt 6):o1428. doi: 10.1107/S1600536810017721

r-2,c-6-Bis(2-methoxyphenyl)-t-3,t-5-dimethylpiperidin-4-one acetic acid solvate

G Aridoss ^a, S Sundaramoorthy ^b, D Velmurugan ^b, K S Park ^a, Y T Jeong ^a,^*

PMCID: PMC2979382 PMID: 21579504

Abstract

In the title compound, C₂₁H₂₅NO₃·C₂H₄O₂, the piperidone ring adopts a chair conformation. The two methoxy groups are nearly coplanar with the aromatic rings to which they are attached. The dihedral angle between the two aromatic rings is 60.9 (2)°. There are two short intramolecular N—H⋯O contacts. The crystal packing is stabilized by intermolecular O—H⋯N and C—H⋯O interactions.

Related literature

For related structures see: Aridoss et al. (2008 ▶),(2009 ▶); Gayathri et al. (2008 ▶). For the synthesis of the title compound, see Noller & Baliah (1948 ▶). For ring conformational analysis, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C₂₁H₂₅NO₃·C₂H₄O₂
M _r = 399.47
Triclinic,
a = 9.3059 (5) Å
b = 10.7052 (8) Å
c = 11.8950 (7) Å
α = 94.432 (3)°
β = 93.341 (2)°
γ = 109.502 (3)°
V = 1109.21 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 292 K
0.25 × 0.23 × 0.2 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.979, T _max = 0.983
19986 measured reflections
5528 independent reflections
3271 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.173
S = 1.00
5528 reflections
271 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810017721/bt5268sup1.cif

e-66-o1428-sup1.cif^{(23KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017721/bt5268Isup2.hkl

e-66-o1428-Isup2.hkl^{(265.2KB, hkl)}

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
O5—H5A⋯N1ⁱ	0.82	1.82	2.642 (2)	178
N1—H1⋯O2	0.869 (18)	2.210 (16)	2.835 (2)	128.6 (14)
N1—H1⋯O3	0.869 (17)	2.322 (18)	2.9241 (17)	126.6 (14)
C19—H19⋯O4ⁱⁱ	0.93	2.51	3.441 (2)	175
C22—H22C⋯O5ⁱⁱⁱ	0.96	2.54	3.482 (3)	167

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

Acknowledgments

GA and YTJ are grateful for the support provided by the second stage of the BK21 program, Republic of Korea. SS and DV thank the TBI X-ray Facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection and the University Grants Commission (UGC&SAP) for financial support.

supplementary crystallographic information

Comment

In continuation of our work on establishing the crystal structure and conformation of 2,6-diaryl piperidine-4-ones and their derivatives (Aridoss et al., 2008, 2009 and Gayathri et al., 2008), we are reporting here the crystal structure of the title compound wherein the piperidone ring adopts chair conformation irrespective of the substituents' on both sides of carbonyl and secondary nitrogen in the ring.

In the present structure, the piperidone ring adopts a chair conformation with atoms N1 and C3 deviating by -0.584 (2) and 0.628 (6) Å, respectively,from the least-sqaures plane defined by the remaining atoms (C1/C2/C4/C5) in the ring. When compared with the reported structures of piperidone derivatives (Gayathri et al., 2008), it is clear that the conformation of the piperidone ring is highly influenced by the substitutions at various positions. The molecule is stabilized by N—H···O intramolecular interaction wherein, N1 atom act as a donor to O2 and O3, generating two S(6) motifs. The crystal packing is stabilized by N—H···O, O—H···N and C—H···O intra and intermolecular interactions. The sum of the bond angles around the atom N1(336.6 (3)°) of the piperidone ring in the molecule is in accordance with sp³ hybridization.

The puckering parameters (Cremer & Pople, 1975) and the smallest displacement asymmetry parameters (Nardelli, 1983) for the piperidine ring are q₂ = 0.041 (1) Å, q₃ = 0.534 (4) Å; Q_T = 0.536 (1) Å and θ = 4.40 (1)°,φ₂ = 135.887 (8)°, respectively.

Experimental

The title compound was prepared by the condensation of 3-pentanone, 2-methoxybenzaldehyde and ammonium acetate in 1:2:1 molar ratio in ethanol as reported by Noller and Baliah (1948) with slight modification. Diffraction quality white crystal was obtained by recrystalization of the crude sample from ethanol.