N-(2-Fluoro­benz­yloxy)-1,3,5-trimethyl-2,6-diphenyl­piperidin-4-imine

Chennan Ramalingan; Seik Weng Ng; Edward R T Tiekink

doi:10.1107/S1600536812029327

. 2012 Jul 4;68(Pt 8):o2312–o2313. doi: 10.1107/S1600536812029327

N-(2-Fluorobenzyloxy)-1,3,5-trimethyl-2,6-diphenylpiperidin-4-imine

Chennan Ramalingan ^a,^‡, Seik Weng Ng ^b,^c, Edward R T Tiekink ^b,^*

PMCID: PMC3414181 PMID: 22904788

Abstract

In the title compound, C₂₇H₂₉FN₂O, the piperidine ring has a twisted boat conformation and all ring substituents occupy equatorial positions. The dihedral angle formed between the phenyl rings is 66.71 (12)°, and the phenyl rings form dihedral angles of 46.60 (13) and 43.75 (13)° with the fluorobenzene ring, which occupies a position coplanar to the methoxy(methylidene)amine residue [N—O—C—C torsion angle = −179.5 (2)°]. In the crystal, a complex network of C—H⋯π interactions connects the molecules into a three-dimensional architecture.

Related literature

For the biological activity of molecules having a 2,6-diarylpiperidine core, see: Ramachandran et al. (2011 ▶); Ramalingan et al. (2004 ▶). For the structures of related chloro and bromo derivatives, see: Ramalingan et al. (2012a ▶,b ▶). For the synthesis, see: Ramalingan et al. (2006 ▶).

Experimental

Crystal data

C₂₇H₂₉FN₂O
M _r = 416.52
Orthorhombic,
a = 7.4004 (3) Å
b = 22.4857 (9) Å
c = 13.4465 (5) Å
V = 2237.54 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.30 × 0.20 × 0.15 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T _min = 0.930, T _max = 1.000
14812 measured reflections
2693 independent reflections
2311 reflections with I > 2σ(I)
R _int = 0.058

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.101
S = 1.03
2693 reflections
280 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812029327/pv2563sup1.cif

e-68-o2312-sup1.cif^{(23.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029327/pv2563Isup2.hkl

e-68-o2312-Isup2.hkl^{(132.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812029327/pv2563Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

Cg1–Cg3 are the centroids of the C1–C6, C16–C21 and C22–C27 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯Cg1ⁱ	0.99	2.96	3.721 (3)	135
C13—H13A⋯Cg2ⁱⁱ	0.98	2.91	3.577 (3)	127
C18—H18⋯Cg3ⁱⁱⁱ	0.95	2.90	3.700 (3)	143
C21—H21⋯Cg2^iv	0.95	2.51	3.446 (3)	167
C25—H25⋯Cg3^v	0.95	2.74	3.654 (3)	160

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

Acknowledgments

The authors are grateful for facilities provided by the Chairman/Management of Kalasalingam University, and thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).

supplementary crystallographic information

Comment

In a program aimed towards synthesizing efficient biological agents, the title compound, (I), was generated (Ramalingan et al., 2006) as molecules with a 2,6-diarylpiperidine core are known to exhibit potent biological activities (Ramachandran et al., 2011; Ramalingan et al., 2004). Herein, the crystal and molecular structure of the title compound is described.

In the title molecule (Fig. 1), the piperidine ring adopts a twist-boat conformation and all ring-substituents occupy equatorial positions. In the chloro (Ramalingan et al., 2012b) and bromo (Ramalingan et al., 2012b) analogues of the title compound, which lack a C-bound methyl substituent and where the piperidine ring adopts a chair conformation, all C-bound substituents are found in equatorial positions and the N-bound methyl group is in a bisectional position (Ramalingan et al., 2012a, 2012b). The dihedral angle formed between the C15–C20 and C21–C26 benzene rings in the title compound is 66.71 (12)°, and each forms a dihedral angle of 46.60 (13) and 43.75 (13)°, respectively, with the fluorobenzene ring, which occupies a position co-planar to the methoxy(methylidene)amine residue, as seen in the N1—O1—C7—C6 torsion angle of -179.5 (2)°. In the aforementioned chloro and bromo derivatives, orthogonal and co-planar orientations were observed in this region of the respective molecule, respectively. The conformation about the imine C8═N1 bond [1.278 (3) Å] is E.

A complex network of C—H···π interactions connects the molecules into a three-dimensional architecture (Table 1 and Fig. 2).

Experimental

For full details of the synthesis, refer to Ramalingan et al. (2006). Re-crystallization was performed by slow evaporation of an ethanolic solution of (I) which afforded colourless crystals. M.pt: 378–379 K.