(4E)-N-[(2-Chloro-phen-yl)meth-oxy]-1,3-dimethyl-2,6-diphenyl-piperidin-4-imine.

In the title compound, C(26)H(27)ClN(2)O, the piperidine ring has a chair conformation and all of the ring substituents at Csp(3) atoms occupy equatorial positions. The dihedral angle formed between the phenyl rings is 48.11 (9)°. The chloro-benzene ring occupies a position orthogonal to the meth-oxy(methyl-idene)amine residue [N-O-C-C torsion angle = -87.90 (15)°]. The conformation about the imine C=N bond [1.278 (2) Å] is E, and the chloro substituent is anti to the piperidine N atom. Helical supra-molecular chains along [010] are sustained by C-H⋯π inter-actions 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 bromo derivative, see: Ramalingan et al. (2012 ▶). For the synthesis, see: Ramalingan et al. (2006 ▶).

Experimental

Crystal data

C26H27ClN2O

M = 418.95

Monoclinic,

a = 20.3043 (8) Å

b = 6.8811 (3) Å

c = 32.2244 (12) Å

β = 98.478 (4)°

V = 4453.1 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.19 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 = 0.846, T max = 1.000

14305 measured reflections

5108 independent reflections

3847 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.118

S = 1.02

5108 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.28 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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812028899/bt5958sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028899/bt5958Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812028899/bt5958Isup3.cml

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

C26H27ClN2O	F(000) = 1776
Mr = 418.95	Dx = 1.250 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4543 reflections
a = 20.3043 (8) Å	θ = 2.2–27.5°
b = 6.8811 (3) Å	µ = 0.19 mm−1
c = 32.2244 (12) Å	T = 100 K
β = 98.478 (4)°	Prism, colourless
V = 4453.1 (3) Å3	0.30 × 0.25 × 0.20 mm
Z = 8

Agilent SuperNova Dual diffractometer with an Atlas detector	5108 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3847 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.041
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.2°
ω scan	h = −19→26
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −8→8
Tmin = 0.846, Tmax = 1.000	l = −41→40
14305 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0478P)2 + 2.1668P] where P = (Fo2 + 2Fc2)/3
5108 reflections	(Δ/σ)max = 0.001
271 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Cl1	0.76604 (2)	0.38812 (7)	0.564062 (15)	0.03838 (15)
O1	0.63144 (6)	0.72592 (17)	0.47058 (3)	0.0276 (3)
N1	0.64825 (7)	0.6556 (2)	0.43184 (4)	0.0244 (3)
N2	0.56479 (6)	0.9658 (2)	0.32797 (4)	0.0210 (3)
C1	0.68498 (8)	0.3178 (2)	0.54424 (5)	0.0233 (4)
C2	0.66062 (9)	0.1447 (3)	0.55791 (5)	0.0287 (4)
H2	0.6880	0.0643	0.5773	0.034*
C3	0.59581 (9)	0.0907 (3)	0.54287 (5)	0.0280 (4)
H3	0.5783	−0.0271	0.5521	0.034*
C4	0.55655 (8)	0.2081 (3)	0.51448 (5)	0.0258 (4)
H4	0.5122	0.1705	0.5041	0.031*
C5	0.58196 (8)	0.3814 (2)	0.50108 (5)	0.0221 (4)
H5	0.5546	0.4610	0.4815	0.027*
C6	0.64648 (8)	0.4393 (2)	0.51585 (5)	0.0199 (3)
C7	0.67419 (9)	0.6302 (3)	0.50347 (5)	0.0256 (4)
H7A	0.6815	0.7164	0.5283	0.031*
H7B	0.7179	0.6071	0.4943	0.031*
C8	0.61070 (8)	0.7273 (2)	0.40023 (5)	0.0227 (4)
C9	0.55388 (8)	0.8646 (3)	0.40074 (5)	0.0260 (4)
H9A	0.5550	0.9163	0.4295	0.031*
H9B	0.5115	0.7929	0.3932	0.031*
C10	0.55575 (8)	1.0353 (2)	0.37012 (5)	0.0219 (4)
H10	0.5940	1.1217	0.3810	0.026*
C11	0.62664 (8)	0.8506 (2)	0.33000 (5)	0.0214 (4)
H11	0.6646	0.9332	0.3431	0.026*
C12	0.62416 (8)	0.6675 (2)	0.35738 (5)	0.0223 (4)
H12	0.5858	0.5863	0.3443	0.027*
C13	0.68726 (9)	0.5454 (3)	0.35879 (5)	0.0286 (4)
H13A	0.6845	0.4323	0.3769	0.043*
H13B	0.7261	0.6240	0.3700	0.043*
H13C	0.6917	0.5016	0.3304	0.043*
C14	0.56727 (9)	1.1334 (3)	0.30007 (5)	0.0288 (4)
H14A	0.5749	1.0881	0.2723	0.043*
H14B	0.6037	1.2199	0.3118	0.043*
H14C	0.5250	1.2040	0.2975	0.043*
C15	0.49163 (8)	1.1488 (2)	0.36936 (5)	0.0213 (3)
C16	0.49022 (8)	1.3168 (2)	0.39308 (5)	0.0237 (4)
H16	0.5306	1.3691	0.4074	0.028*
C17	0.43008 (9)	1.4094 (3)	0.39607 (5)	0.0271 (4)
H17	0.4296	1.5236	0.4126	0.033*
C18	0.37128 (9)	1.3360 (3)	0.37519 (5)	0.0277 (4)
H18	0.3302	1.3975	0.3778	0.033*
C19	0.37231 (9)	1.1719 (3)	0.35031 (5)	0.0295 (4)
H19	0.3320	1.1231	0.3352	0.035*
C20	0.43214 (8)	1.0787 (3)	0.34742 (5)	0.0269 (4)
H20	0.4325	0.9663	0.3304	0.032*
C21	0.63939 (8)	0.7940 (2)	0.28645 (5)	0.0220 (4)
C22	0.69737 (9)	0.8528 (3)	0.27206 (5)	0.0283 (4)
H22	0.7291	0.9288	0.2897	0.034*
C23	0.70963 (10)	0.8021 (3)	0.23233 (6)	0.0354 (5)
H23	0.7494	0.8442	0.2228	0.042*
C24	0.66437 (10)	0.6911 (3)	0.20661 (6)	0.0346 (5)
H24	0.6727	0.6571	0.1793	0.042*
C25	0.60686 (10)	0.6291 (3)	0.22063 (6)	0.0340 (4)
H25	0.5758	0.5511	0.2030	0.041*
C26	0.59421 (9)	0.6802 (3)	0.26037 (5)	0.0289 (4)
H26	0.5545	0.6373	0.2698	0.035*

	U11	U22	U33	U12	U13	U23
Cl1	0.0221 (2)	0.0391 (3)	0.0494 (3)	−0.00554 (19)	−0.00987 (19)	0.0090 (2)
O1	0.0368 (7)	0.0258 (7)	0.0208 (6)	0.0004 (5)	0.0067 (5)	0.0050 (5)
N1	0.0284 (8)	0.0227 (8)	0.0231 (7)	−0.0036 (6)	0.0070 (6)	0.0011 (6)
N2	0.0207 (7)	0.0217 (7)	0.0205 (7)	0.0014 (6)	0.0030 (5)	0.0023 (6)
C1	0.0201 (8)	0.0235 (9)	0.0254 (8)	−0.0021 (7)	0.0002 (6)	−0.0009 (7)
C2	0.0303 (10)	0.0243 (10)	0.0293 (9)	0.0004 (7)	−0.0023 (7)	0.0061 (8)
C3	0.0324 (10)	0.0208 (9)	0.0302 (9)	−0.0057 (7)	0.0029 (7)	0.0031 (8)
C4	0.0230 (9)	0.0264 (9)	0.0271 (9)	−0.0069 (7)	0.0005 (7)	−0.0020 (8)
C5	0.0224 (9)	0.0249 (9)	0.0182 (8)	−0.0005 (7)	0.0002 (6)	0.0003 (7)
C6	0.0230 (8)	0.0215 (9)	0.0154 (7)	−0.0013 (6)	0.0042 (6)	−0.0005 (7)
C7	0.0275 (9)	0.0259 (10)	0.0222 (8)	−0.0054 (7)	0.0000 (7)	0.0034 (7)
C8	0.0211 (9)	0.0205 (9)	0.0264 (9)	−0.0034 (7)	0.0036 (7)	0.0053 (7)
C9	0.0264 (9)	0.0273 (10)	0.0256 (9)	0.0020 (7)	0.0088 (7)	0.0045 (7)
C10	0.0217 (9)	0.0226 (9)	0.0211 (8)	−0.0029 (7)	0.0017 (6)	−0.0015 (7)
C11	0.0178 (8)	0.0231 (9)	0.0230 (8)	−0.0016 (6)	0.0020 (6)	0.0004 (7)
C12	0.0191 (8)	0.0241 (9)	0.0238 (8)	−0.0010 (7)	0.0033 (6)	0.0025 (7)
C13	0.0287 (10)	0.0310 (10)	0.0266 (9)	0.0065 (8)	0.0058 (7)	0.0053 (8)
C14	0.0345 (10)	0.0281 (10)	0.0244 (9)	0.0041 (8)	0.0057 (7)	0.0051 (8)
C15	0.0237 (9)	0.0211 (9)	0.0194 (8)	−0.0012 (7)	0.0041 (6)	0.0016 (7)
C16	0.0292 (9)	0.0235 (9)	0.0187 (8)	−0.0060 (7)	0.0047 (7)	−0.0001 (7)
C17	0.0384 (11)	0.0199 (9)	0.0255 (9)	0.0007 (7)	0.0129 (7)	−0.0006 (7)
C18	0.0287 (10)	0.0285 (10)	0.0275 (9)	0.0063 (7)	0.0092 (7)	0.0026 (8)
C19	0.0229 (9)	0.0339 (10)	0.0309 (9)	−0.0002 (7)	0.0008 (7)	−0.0027 (8)
C20	0.0251 (9)	0.0260 (9)	0.0295 (9)	−0.0011 (7)	0.0031 (7)	−0.0078 (8)
C21	0.0223 (9)	0.0219 (9)	0.0213 (8)	0.0037 (7)	0.0018 (6)	0.0038 (7)
C22	0.0309 (10)	0.0261 (10)	0.0286 (9)	−0.0006 (7)	0.0069 (7)	0.0043 (8)
C23	0.0391 (11)	0.0359 (11)	0.0347 (10)	0.0077 (9)	0.0173 (8)	0.0091 (9)
C24	0.0441 (12)	0.0369 (11)	0.0234 (9)	0.0187 (9)	0.0069 (8)	0.0024 (8)
C25	0.0356 (11)	0.0360 (11)	0.0273 (9)	0.0094 (8)	−0.0058 (8)	−0.0036 (8)
C26	0.0233 (9)	0.0362 (11)	0.0261 (9)	0.0011 (8)	−0.0004 (7)	−0.0018 (8)

Cl1—C1	1.7439 (17)	C12—C13	1.527 (2)
O1—N1	1.4266 (17)	C12—H12	1.0000
O1—C7	1.4280 (19)	C13—H13A	0.9800
N1—C8	1.278 (2)	C13—H13B	0.9800
N2—C14	1.467 (2)	C13—H13C	0.9800
N2—C11	1.479 (2)	C14—H14A	0.9800
N2—C10	1.477 (2)	C14—H14B	0.9800
C1—C2	1.386 (2)	C14—H14C	0.9800
C1—C6	1.391 (2)	C15—C16	1.389 (2)
C2—C3	1.384 (2)	C15—C20	1.393 (2)
C2—H2	0.9500	C16—C17	1.393 (2)
C3—C4	1.382 (2)	C16—H16	0.9500
C3—H3	0.9500	C17—C18	1.377 (3)
C4—C5	1.393 (2)	C17—H17	0.9500
C4—H4	0.9500	C18—C19	1.387 (3)
C5—C6	1.385 (2)	C18—H18	0.9500
C5—H5	0.9500	C19—C20	1.389 (2)
C6—C7	1.506 (2)	C19—H19	0.9500
C7—H7A	0.9900	C20—H20	0.9500
C7—H7B	0.9900	C21—C26	1.391 (2)
C8—C9	1.493 (2)	C21—C22	1.388 (2)
C8—C12	1.504 (2)	C22—C23	1.385 (2)
C9—C10	1.538 (2)	C22—H22	0.9500
C9—H9A	0.9900	C23—C24	1.375 (3)
C9—H9B	0.9900	C23—H23	0.9500
C10—C15	1.515 (2)	C24—C25	1.380 (3)
C10—H10	1.0000	C24—H24	0.9500
C11—C21	1.515 (2)	C25—C26	1.388 (2)
C11—C12	1.543 (2)	C25—H25	0.9500
C11—H11	1.0000	C26—H26	0.9500
N1—O1—C7	107.18 (12)	C13—C12—C11	111.60 (13)
C8—N1—O1	112.01 (13)	C8—C12—H12	107.7
C14—N2—C11	110.05 (12)	C13—C12—H12	107.7
C14—N2—C10	109.23 (13)	C11—C12—H12	107.7
C11—N2—C10	110.66 (12)	C12—C13—H13A	109.5
C2—C1—C6	122.22 (15)	C12—C13—H13B	109.5
C2—C1—Cl1	118.92 (13)	H13A—C13—H13B	109.5
C6—C1—Cl1	118.84 (13)	C12—C13—H13C	109.5
C3—C2—C1	118.97 (16)	H13A—C13—H13C	109.5
C3—C2—H2	120.5	H13B—C13—H13C	109.5
C1—C2—H2	120.5	N2—C14—H14A	109.5
C4—C3—C2	120.05 (16)	N2—C14—H14B	109.5
C4—C3—H3	120.0	H14A—C14—H14B	109.5
C2—C3—H3	120.0	N2—C14—H14C	109.5
C3—C4—C5	120.12 (16)	H14A—C14—H14C	109.5
C3—C4—H4	119.9	H14B—C14—H14C	109.5
C5—C4—H4	119.9	C16—C15—C20	118.76 (16)
C6—C5—C4	120.97 (15)	C16—C15—C10	120.51 (15)
C6—C5—H5	119.5	C20—C15—C10	120.56 (15)
C4—C5—H5	119.5	C15—C16—C17	120.54 (16)
C5—C6—C1	117.67 (15)	C15—C16—H16	119.7
C5—C6—C7	122.10 (15)	C17—C16—H16	119.7
C1—C6—C7	120.18 (14)	C18—C17—C16	120.28 (16)
O1—C7—C6	112.89 (13)	C18—C17—H17	119.9
O1—C7—H7A	109.0	C16—C17—H17	119.9
C6—C7—H7A	109.0	C17—C18—C19	119.67 (16)
O1—C7—H7B	109.0	C17—C18—H18	120.2
C6—C7—H7B	109.0	C19—C18—H18	120.2
H7A—C7—H7B	107.8	C18—C19—C20	120.18 (16)
N1—C8—C9	127.36 (15)	C18—C19—H19	119.9
N1—C8—C12	117.26 (15)	C20—C19—H19	119.9
C9—C8—C12	115.38 (14)	C19—C20—C15	120.51 (16)
C8—C9—C10	112.57 (13)	C19—C20—H20	119.7
C8—C9—H9A	109.1	C15—C20—H20	119.7
C10—C9—H9A	109.1	C26—C21—C22	118.62 (15)
C8—C9—H9B	109.1	C26—C21—C11	121.13 (15)
C10—C9—H9B	109.1	C22—C21—C11	120.25 (15)
H9A—C9—H9B	107.8	C23—C22—C21	120.83 (18)
N2—C10—C15	112.02 (13)	C23—C22—H22	119.6
N2—C10—C9	111.17 (13)	C21—C22—H22	119.6
C15—C10—C9	107.56 (13)	C24—C23—C22	120.14 (18)
N2—C10—H10	108.7	C24—C23—H23	119.9
C15—C10—H10	108.7	C22—C23—H23	119.9
C9—C10—H10	108.7	C23—C24—C25	119.79 (17)
N2—C11—C21	110.91 (13)	C23—C24—H24	120.1
N2—C11—C12	111.35 (12)	C25—C24—H24	120.1
C21—C11—C12	110.13 (13)	C24—C25—C26	120.29 (18)
N2—C11—H11	108.1	C24—C25—H25	119.9
C21—C11—H11	108.1	C26—C25—H25	119.9
C12—C11—H11	108.1	C21—C26—C25	120.32 (17)
C8—C12—C13	112.86 (14)	C21—C26—H26	119.8
C8—C12—C11	109.08 (14)	C25—C26—H26	119.8
C7—O1—N1—C8	177.41 (14)	N1—C8—C12—C11	−131.39 (16)
C6—C1—C2—C3	0.0 (3)	C9—C8—C12—C11	49.02 (18)
Cl1—C1—C2—C3	178.66 (13)	N2—C11—C12—C8	−55.90 (17)
C1—C2—C3—C4	0.4 (3)	C21—C11—C12—C8	−179.37 (13)
C2—C3—C4—C5	−0.3 (3)	N2—C11—C12—C13	178.71 (13)
C3—C4—C5—C6	−0.1 (2)	C21—C11—C12—C13	55.24 (18)
C4—C5—C6—C1	0.4 (2)	N2—C10—C15—C16	−138.80 (15)
C4—C5—C6—C7	−177.07 (15)	C9—C10—C15—C16	98.76 (17)
C2—C1—C6—C5	−0.3 (2)	N2—C10—C15—C20	46.1 (2)
Cl1—C1—C6—C5	−179.05 (12)	C9—C10—C15—C20	−76.34 (18)
C2—C1—C6—C7	177.20 (16)	C20—C15—C16—C17	2.3 (2)
Cl1—C1—C6—C7	−1.5 (2)	C10—C15—C16—C17	−172.88 (14)
N1—O1—C7—C6	−87.90 (15)	C15—C16—C17—C18	−0.6 (2)
C5—C6—C7—O1	−9.4 (2)	C16—C17—C18—C19	−1.5 (3)
C1—C6—C7—O1	173.12 (14)	C17—C18—C19—C20	1.9 (3)
O1—N1—C8—C9	−1.6 (2)	C18—C19—C20—C15	−0.1 (3)
O1—N1—C8—C12	178.88 (13)	C16—C15—C20—C19	−2.0 (2)
N1—C8—C9—C10	133.48 (17)	C10—C15—C20—C19	173.19 (15)
C12—C8—C9—C10	−47.0 (2)	N2—C11—C21—C26	−60.8 (2)
C14—N2—C10—C15	60.47 (17)	C12—C11—C21—C26	62.9 (2)
C11—N2—C10—C15	−178.23 (13)	N2—C11—C21—C22	120.20 (16)
C14—N2—C10—C9	−179.16 (13)	C12—C11—C21—C22	−116.07 (17)
C11—N2—C10—C9	−57.86 (17)	C26—C21—C22—C23	1.0 (3)
C8—C9—C10—N2	49.92 (19)	C11—C21—C22—C23	−179.98 (16)
C8—C9—C10—C15	172.88 (14)	C21—C22—C23—C24	−0.4 (3)
C14—N2—C11—C21	−54.15 (17)	C22—C23—C24—C25	−0.4 (3)
C10—N2—C11—C21	−174.97 (13)	C23—C24—C25—C26	0.7 (3)
C14—N2—C11—C12	−177.17 (13)	C22—C21—C26—C25	−0.7 (3)
C10—N2—C11—C12	62.01 (17)	C11—C21—C26—C25	−179.72 (16)
N1—C8—C12—C13	−6.7 (2)	C24—C25—C26—C21	−0.1 (3)
C9—C8—C12—C13	173.67 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···Cg1i	0.95	2.69	3.556 (2)	151
C3—H3···Cg2ii	0.95	2.90	3.6852 (19)	141

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C15–C20 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯Cg1i	0.95	2.69	3.556 (2)	151
C3—H3⋯Cg2ii	0.95	2.90	3.6852 (19)	141

Symmetry codes: (i) ; (ii) .