2-Cyclo­hexyl-4-[(3,5-dimethyl­piperidin-1-yl)meth­yl]-5-methyl­phenol

Gui-Yun Duan; Feng-Guang Guo; Cheng-Cai Xia

doi:10.1107/S1600536809001305

. 2009 Feb 4;65(Pt 3):o456. doi: 10.1107/S1600536809001305

2-Cyclohexyl-4-[(3,5-dimethylpiperidin-1-yl)methyl]-5-methylphenol

Gui-Yun Duan ^a,^*, Feng-Guang Guo ^a, Cheng-Cai Xia ^a

PMCID: PMC2968627 PMID: 21582128

Abstract

The title compound, C₂₁H₃₃NO, crystallizes with three independent molecules in the asymmetric unit. The cyclohexane and piperidine rings adopt chair conformations. The crystal packing is stabilized by intermolecular O—H⋯N and C—H⋯O hydrogen bonds, and by weak π–π stacking interactions [centroid–centroid distance = 3.876 (2) Å].

Related literature

For the biological activity of amidomethylphenol derivatives, see: Zhang et al. (1986 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₁H₃₃NO
M _r = 315.48
Triclinic,
a = 12.0551 (7) Å
b = 16.5513 (10) Å
c = 16.7371 (10) Å
α = 78.969 (1)°
β = 69.354 (1)°
γ = 71.951 (1)°
V = 2958.6 (3) Å³
Z = 6
Mo Kα radiation
μ = 0.06 mm⁻¹
T = 273 (2) K
0.18 × 0.15 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
15478 measured reflections
10326 independent reflections
6658 reflections with I > 2σ(I)
R _int = 0.016

Refinement

R[F ² > 2σ(F ²)] = 0.067
wR(F ²) = 0.219
S = 1.03
10326 reflections
634 parameters
1296 restraints
H-atom parameters constrained
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.60 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809001305/hg2466sup1.cif

e-65-0o456-sup1.cif^{(43.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001305/hg2466Isup2.hkl

e-65-0o456-Isup2.hkl^{(504.9KB, 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
O1—H1⋯N1ⁱ	0.82	2.03	2.843 (3)	170
C13—H13B⋯O1ⁱ	0.96	2.52	3.335 (4)	143
O2—H2⋯N2ⁱⁱ	0.82	2.03	2.845 (3)	171
C34—H34C⋯O2ⁱⁱ	0.96	2.49	3.348 (4)	149
O3—H3⋯N3ⁱⁱⁱ	0.82	2.02	2.831 (3)	174
C55—H55C⋯O3ⁱⁱⁱ	0.96	2.58	3.404 (4)	145

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

supplementary crystallographic information

Comment

4-amidomethyl-phenol derivatives have anti-inflammatory active [Zhang et al., 1986]. The title compound is a derivative of it. In this paper, we report the crystal structure of the title compound.

The title compound, C₂₁H₃₃NO, crystallizes with three independent molecules in the asymmetric unit; all bond lengths are normal (Allen et al., 1987). The cyclohexane (C7—C12; C28—C33; C49—C54) and piperidine ring (N1/C15—C19; N2/C36—C40; N3/C57—C61) adopt chair conformations. The relatively short distance of 3.876 (2)Å between the centroids of benzene ring C43—C48 [at (–X,-Y,1-Z)] indicates the presence of weak π-π interactions, which contribute to the stability of the crystal packing. The crystal packing is also stabilized by intermolecular O—H···N and C—H···O hydrogen bonds,

Experimental

The title compound was prepared by reaction of 2-cyclohexyl-5-methylphenol (1.90 g, 0.01 mol) with 3,5-dimethylpiperidine(1.13 g, 0.01 mol) and 36% formaldehyde solution(1.00 g, 0.012 mol) in 10 mL of 95% alcohol under reflux for 3 h. After removing of the solvent, the residue was recrystallized from ethanol to afford 2.74 g of the title compound with yield of 87%. Crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of a methanol solution at room temperature for two weeks.