(4E)-N-[(2-Bromo­phen­yl)meth­oxy]-1,3-dimethyl-2,6-diphenyl­piperidin-4-imine

Chennan Ramalingan; Seik Weng Ng; Edward R T Tiekink

doi:10.1107/S1600536812028887

. 2012 Jun 30;68(Pt 7):o2267. doi: 10.1107/S1600536812028887

(4E)-N-[(2-Bromophenyl)methoxy]-1,3-dimethyl-2,6-diphenylpiperidin-4-imine

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

PMCID: PMC3394050 PMID: 22798915

Abstract

In the title compound, C₂₆H₂₇BrN₂O, the piperidine ring has a chair conformation and all ring substituents occupy equatorial positions, apart from the double-bonded N atom, which occupies a bisectional position. The dihedral angle formed between the phenyl rings is 61.18 (19)°, and the phenyl rings form dihedral angles of 49.78 (19) and 69.2 (18)° with the bromobenzene ring. The latter is coplanar with the methoxy(methylidene)amine fragment [N—O—C—C torsion angle = −171.7 (2)°]. Linear supramolecular chains, approximately along [112], sustained by C—H⋯π interactions, feature in the crystal packing.

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 structure of the chloro derivative, see: Ramalingan et al. (2012 ▶). For the synthesis, see: Ramalingan et al. (2006 ▶).

Experimental

Crystal data

C₂₆H₂₇BrN₂O
M _r = 463.41
Triclinic,
a = 10.4425 (6) Å
b = 11.2544 (6) Å
c = 11.7035 (6) Å
α = 106.635 (5)°
β = 104.289 (5)°
γ = 113.558 (5)°
V = 1101.14 (14) Å³
Z = 2
Mo Kα radiation
μ = 1.89 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T _min = 0.705, T _max = 1.000
16609 measured reflections
5097 independent reflections
4176 reflections with I > 2σ(I)
R _int = 0.060

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.109
S = 1.08
5097 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.80 e Å⁻³
Δρ_min = −0.47 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/S1600536812028887/bt5957sup1.cif

e-68-o2267-sup1.cif^{(22.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028887/bt5957Isup2.hkl

e-68-o2267-Isup2.hkl^{(249.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812028887/bt5957Isup3.cml

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

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

Cg1 is the centroid of the C21–C26 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯Cg1ⁱ	0.95	2.77	3.626 (4)	150

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Symmetry code: (i) Inline graphic .

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

The original synthesis (Ramalingan et al., 2006) of the title compound, (I), was motivated by the diverse range of molecules possessing a 2,6-diarylpiperidine core that exhibit potent biological activities (Ramachandran et al., 2011; Ramalingan et al., 2004). Herein, the crystal and molecular structure of (I) is described.

In (I), Fig. 1, the piperidine ring has a chair conformation and all ring-substituents bound to C occupy equatorial positions, as found for the chloro derivative (Ramalingan et al., 2012), but the the double bonded N atom occupies a bisectional position. The dihedral angle formed between the C15–C20 and C21–C26 phenyl rings is 61.18 (19)°, and each forms a dihedral angle of 49.78 (19) and 69.2 (18)°, respectively, with the bromobenzene ring, which occupies a position co-planar to the methoxy(methylidene)amine residue as seen in the N1—O1—C7—C6 torsion angle of -171.7 (2)°. This is in contrast to the orthogonal disposition in the chloro derivative (Ramalingan et al., 2012). The conformation about the imine C8═N1 bond [1.281 (4) Å] is E.

In the crystal packing, linear supramolecular chains are formed via C—H···π interactions, Fig. 2 and Table 1. These assemble into layers parallel to (1 0 1) and stack without specific intermolecular interactions between the chains, Fig. 3.

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: 378–378 K.