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

In the title compound, C(26)H(27)BrN(2)O, the piperidine ring has a chair conformation and all ring substituents occupy equatorial positions, apart from the double-bonded N atom, which occupies a bis-ectional 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 bromo-benzene ring. The latter is coplanar with the meth-oxy(methyl-idene)amine fragment [N-O-C-C torsion angle = -171.7 (2)°]. Linear supra-molecular chains, approximately along [112], sustained by C-H⋯π inter-actions, 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 = 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

Δρmax = 0.80 e Å−3

Δρmin = −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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812028887/bt5957sup1.cif

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

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

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

C26H27BrN2O	Z = 2
Mr = 463.41	F(000) = 480
Triclinic, P1	Dx = 1.398 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.4425 (6) Å	Cell parameters from 3935 reflections
b = 11.2544 (6) Å	θ = 2.2–27.5°
c = 11.7035 (6) Å	µ = 1.89 mm−1
α = 106.635 (5)°	T = 100 K
β = 104.289 (5)°	Prism, colourless
γ = 113.558 (5)°	0.30 × 0.25 × 0.20 mm
V = 1101.14 (14) Å3

Agilent SuperNova Dual diffractometer with an Atlas detector	5097 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4176 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.060
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.2°
ω scan	h = −13→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −14→14
Tmin = 0.705, Tmax = 1.000	l = −15→15
16609 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0415P)2 + 0.7452P] where P = (Fo2 + 2Fc2)/3
5097 reflections	(Δ/σ)max = 0.001
271 parameters	Δρmax = 0.80 e Å−3
0 restraints	Δρmin = −0.47 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
Br1	0.34353 (4)	0.50273 (3)	0.06043 (3)	0.01907 (11)
O1	0.5312 (2)	0.3306 (2)	0.32446 (19)	0.0175 (5)
N1	0.6428 (3)	0.4466 (3)	0.4478 (2)	0.0167 (5)
N2	0.9330 (3)	0.3545 (2)	0.6563 (2)	0.0136 (5)
C1	0.2741 (3)	0.3069 (3)	0.0280 (3)	0.0144 (6)
C2	0.1471 (4)	0.2010 (3)	−0.0865 (3)	0.0195 (7)
H2	0.0955	0.2262	−0.1457	0.023*
C3	0.0963 (4)	0.0579 (3)	−0.1135 (3)	0.0217 (7)
H3	0.0098	−0.0158	−0.1919	0.026*
C4	0.1719 (4)	0.0225 (3)	−0.0257 (3)	0.0201 (7)
H4	0.1381	−0.0757	−0.0448	0.024*
C5	0.2961 (4)	0.1291 (3)	0.0890 (3)	0.0186 (6)
H5	0.3452	0.1032	0.1491	0.022*
C6	0.3511 (3)	0.2740 (3)	0.1189 (3)	0.0140 (6)
C7	0.4854 (3)	0.3926 (3)	0.2434 (3)	0.0169 (6)
H7A	0.5713	0.4472	0.2236	0.020*
H7B	0.4564	0.4597	0.2892	0.020*
C8	0.7003 (3)	0.4035 (3)	0.5256 (3)	0.0155 (6)
C9	0.6668 (3)	0.2537 (3)	0.4985 (3)	0.0175 (6)
H9A	0.5930	0.1878	0.4064	0.021*
H9B	0.6199	0.2216	0.5558	0.021*
C10	0.8151 (3)	0.2486 (3)	0.5232 (3)	0.0143 (6)
H10	0.8553	0.2735	0.4591	0.017*
C11	0.9663 (3)	0.5032 (3)	0.6808 (3)	0.0134 (6)
H11	1.0066	0.5283	0.6168	0.016*
C12	0.8204 (3)	0.5149 (3)	0.6595 (3)	0.0156 (6)
H12	0.7814	0.4915	0.7247	0.019*
C13	0.8565 (4)	0.6682 (3)	0.6841 (3)	0.0202 (7)
H13A	0.7629	0.6732	0.6726	0.030*
H13B	0.8958	0.6943	0.6218	0.030*
H13C	0.9338	0.7351	0.7735	0.030*
C14	1.0753 (3)	0.3510 (3)	0.6710 (3)	0.0163 (6)
H14A	1.0553	0.2535	0.6543	0.024*
H14B	1.1532	0.4181	0.7602	0.024*
H14C	1.1122	0.3791	0.6084	0.024*
C15	0.7794 (3)	0.0967 (3)	0.4983 (3)	0.0163 (6)
C16	0.7581 (4)	0.0031 (3)	0.3793 (3)	0.0217 (7)
H16	0.7705	0.0358	0.3142	0.026*
C17	0.7188 (4)	−0.1383 (3)	0.3541 (3)	0.0276 (8)
H17	0.7037	−0.2016	0.2718	0.033*
C18	0.7016 (4)	−0.1870 (3)	0.4482 (3)	0.0245 (7)
H18	0.6760	−0.2831	0.4313	0.029*
C19	0.7219 (4)	−0.0947 (3)	0.5671 (3)	0.0215 (7)
H19	0.7103	−0.1276	0.6322	0.026*
C20	0.7592 (3)	0.0458 (3)	0.5917 (3)	0.0183 (6)
H20	0.7711	0.1080	0.6731	0.022*
C21	1.0900 (3)	0.6096 (3)	0.8177 (3)	0.0139 (6)
C22	1.0586 (4)	0.6152 (3)	0.9273 (3)	0.0157 (6)
H22	0.9584	0.5521	0.9163	0.019*
C23	1.1716 (4)	0.7117 (3)	1.0529 (3)	0.0202 (7)
H23	1.1477	0.7146	1.1266	0.024*
C24	1.3185 (4)	0.8035 (3)	1.0709 (3)	0.0220 (7)
H24	1.3960	0.8684	1.1567	0.026*
C25	1.3518 (4)	0.8000 (3)	0.9626 (3)	0.0226 (7)
H25	1.4522	0.8631	0.9741	0.027*
C26	1.2381 (4)	0.7042 (3)	0.8374 (3)	0.0186 (6)
H26	1.2617	0.7031	0.7639	0.022*

	U11	U22	U33	U12	U13	U23
Br1	0.02166 (19)	0.01454 (16)	0.02196 (17)	0.01032 (14)	0.00659 (13)	0.00942 (12)
O1	0.0184 (12)	0.0116 (10)	0.0135 (10)	0.0054 (9)	−0.0008 (9)	0.0035 (8)
N1	0.0165 (14)	0.0104 (12)	0.0142 (12)	0.0046 (11)	0.0012 (11)	0.0016 (10)
N2	0.0120 (13)	0.0097 (12)	0.0143 (12)	0.0037 (10)	0.0018 (10)	0.0049 (10)
C1	0.0162 (16)	0.0123 (14)	0.0195 (15)	0.0084 (13)	0.0095 (13)	0.0094 (12)
C2	0.0195 (17)	0.0192 (16)	0.0176 (15)	0.0092 (14)	0.0044 (13)	0.0089 (13)
C3	0.0189 (17)	0.0183 (16)	0.0154 (15)	0.0061 (14)	−0.0003 (13)	0.0027 (13)
C4	0.0206 (18)	0.0136 (15)	0.0223 (16)	0.0075 (14)	0.0070 (14)	0.0064 (13)
C5	0.0219 (17)	0.0173 (16)	0.0189 (15)	0.0120 (14)	0.0068 (13)	0.0090 (13)
C6	0.0125 (15)	0.0150 (15)	0.0153 (14)	0.0076 (13)	0.0060 (12)	0.0064 (12)
C7	0.0143 (16)	0.0144 (15)	0.0180 (15)	0.0073 (13)	0.0009 (13)	0.0070 (12)
C8	0.0132 (15)	0.0135 (15)	0.0165 (15)	0.0050 (13)	0.0043 (12)	0.0065 (12)
C9	0.0165 (16)	0.0108 (14)	0.0176 (15)	0.0037 (13)	0.0020 (13)	0.0056 (12)
C10	0.0166 (16)	0.0112 (14)	0.0118 (14)	0.0060 (13)	0.0040 (12)	0.0039 (11)
C11	0.0149 (15)	0.0103 (14)	0.0140 (14)	0.0064 (12)	0.0050 (12)	0.0049 (11)
C12	0.0174 (16)	0.0134 (15)	0.0158 (15)	0.0080 (13)	0.0058 (13)	0.0069 (12)
C13	0.0217 (18)	0.0159 (16)	0.0185 (16)	0.0102 (14)	0.0024 (13)	0.0058 (13)
C14	0.0163 (16)	0.0148 (15)	0.0169 (15)	0.0080 (13)	0.0062 (13)	0.0062 (12)
C15	0.0136 (16)	0.0128 (15)	0.0178 (15)	0.0067 (13)	0.0024 (12)	0.0043 (12)
C16	0.0249 (18)	0.0193 (16)	0.0207 (16)	0.0112 (15)	0.0091 (14)	0.0087 (13)
C17	0.032 (2)	0.0167 (17)	0.0256 (18)	0.0128 (16)	0.0097 (16)	0.0005 (14)
C18	0.0226 (18)	0.0115 (15)	0.0364 (19)	0.0099 (14)	0.0093 (15)	0.0071 (14)
C19	0.0177 (17)	0.0171 (16)	0.0283 (18)	0.0079 (14)	0.0058 (14)	0.0122 (14)
C20	0.0185 (17)	0.0122 (15)	0.0181 (15)	0.0066 (13)	0.0042 (13)	0.0033 (12)
C21	0.0153 (16)	0.0082 (13)	0.0170 (15)	0.0063 (12)	0.0046 (12)	0.0052 (11)
C22	0.0164 (16)	0.0122 (14)	0.0193 (15)	0.0083 (13)	0.0058 (13)	0.0078 (12)
C23	0.0286 (19)	0.0157 (15)	0.0176 (15)	0.0152 (15)	0.0060 (14)	0.0062 (13)
C24	0.0246 (18)	0.0120 (15)	0.0174 (16)	0.0102 (14)	−0.0027 (14)	−0.0007 (12)
C25	0.0171 (17)	0.0145 (15)	0.0285 (18)	0.0072 (14)	0.0033 (14)	0.0060 (13)
C26	0.0208 (17)	0.0144 (15)	0.0227 (16)	0.0099 (14)	0.0095 (14)	0.0089 (13)

Br1—C1	1.906 (3)	C12—C13	1.531 (4)
O1—N1	1.421 (3)	C12—H12	1.0000
O1—C7	1.428 (3)	C13—H13A	0.9800
N1—C8	1.281 (4)	C13—H13B	0.9800
N2—C14	1.471 (4)	C13—H13C	0.9800
N2—C10	1.477 (4)	C14—H14A	0.9800
N2—C11	1.487 (3)	C14—H14B	0.9800
C1—C2	1.386 (4)	C14—H14C	0.9800
C1—C6	1.398 (4)	C15—C16	1.385 (4)
C2—C3	1.385 (4)	C15—C20	1.394 (4)
C2—H2	0.9500	C16—C17	1.392 (4)
C3—C4	1.386 (4)	C16—H16	0.9500
C3—H3	0.9500	C17—C18	1.382 (5)
C4—C5	1.378 (4)	C17—H17	0.9500
C4—H4	0.9500	C18—C19	1.383 (4)
C5—C6	1.392 (4)	C18—H18	0.9500
C5—H5	0.9500	C19—C20	1.389 (4)
C6—C7	1.501 (4)	C19—H19	0.9500
C7—H7A	0.9900	C20—H20	0.9500
C7—H7B	0.9900	C21—C22	1.392 (4)
C8—C9	1.494 (4)	C21—C26	1.394 (4)
C8—C12	1.500 (4)	C22—C23	1.392 (4)
C9—C10	1.532 (4)	C22—H22	0.9500
C9—H9A	0.9900	C23—C24	1.384 (5)
C9—H9B	0.9900	C23—H23	0.9500
C10—C15	1.516 (4)	C24—C25	1.389 (5)
C10—H10	1.0000	C24—H24	0.9500
C11—C21	1.521 (4)	C25—C26	1.391 (4)
C11—C12	1.547 (4)	C25—H25	0.9500
C11—H11	1.0000	C26—H26	0.9500
N1—O1—C7	106.7 (2)	C13—C12—C11	111.2 (2)
C8—N1—O1	111.9 (2)	C8—C12—H12	107.7
C14—N2—C10	108.7 (2)	C13—C12—H12	107.7
C14—N2—C11	108.3 (2)	C11—C12—H12	107.7
C10—N2—C11	111.8 (2)	C12—C13—H13A	109.5
C2—C1—C6	122.0 (3)	C12—C13—H13B	109.5
C2—C1—Br1	118.1 (2)	H13A—C13—H13B	109.5
C6—C1—Br1	119.8 (2)	C12—C13—H13C	109.5
C3—C2—C1	119.2 (3)	H13A—C13—H13C	109.5
C3—C2—H2	120.4	H13B—C13—H13C	109.5
C1—C2—H2	120.4	N2—C14—H14A	109.5
C2—C3—C4	119.9 (3)	N2—C14—H14B	109.5
C2—C3—H3	120.1	H14A—C14—H14B	109.5
C4—C3—H3	120.1	N2—C14—H14C	109.5
C5—C4—C3	120.2 (3)	H14A—C14—H14C	109.5
C5—C4—H4	119.9	H14B—C14—H14C	109.5
C3—C4—H4	119.9	C16—C15—C20	118.6 (3)
C4—C5—C6	121.5 (3)	C16—C15—C10	120.6 (3)
C4—C5—H5	119.3	C20—C15—C10	120.8 (3)
C6—C5—H5	119.3	C15—C16—C17	120.7 (3)
C5—C6—C1	117.2 (3)	C15—C16—H16	119.7
C5—C6—C7	122.7 (3)	C17—C16—H16	119.7
C1—C6—C7	120.1 (3)	C18—C17—C16	120.3 (3)
O1—C7—C6	108.7 (2)	C18—C17—H17	119.9
O1—C7—H7A	110.0	C16—C17—H17	119.9
C6—C7—H7A	110.0	C17—C18—C19	119.6 (3)
O1—C7—H7B	110.0	C17—C18—H18	120.2
C6—C7—H7B	110.0	C19—C18—H18	120.2
H7A—C7—H7B	108.3	C18—C19—C20	120.1 (3)
N1—C8—C9	127.9 (3)	C18—C19—H19	119.9
N1—C8—C12	117.7 (3)	C20—C19—H19	119.9
C9—C8—C12	114.4 (2)	C19—C20—C15	120.7 (3)
C8—C9—C10	109.9 (2)	C19—C20—H20	119.6
C8—C9—H9A	109.7	C15—C20—H20	119.6
C10—C9—H9A	109.7	C22—C21—C26	118.0 (3)
C8—C9—H9B	109.7	C22—C21—C11	120.8 (3)
C10—C9—H9B	109.7	C26—C21—C11	121.2 (3)
H9A—C9—H9B	108.2	C21—C22—C23	121.1 (3)
N2—C10—C15	112.0 (2)	C21—C22—H22	119.5
N2—C10—C9	111.4 (2)	C23—C22—H22	119.5
C15—C10—C9	109.2 (2)	C24—C23—C22	120.2 (3)
N2—C10—H10	108.1	C24—C23—H23	119.9
C15—C10—H10	108.1	C22—C23—H23	119.9
C9—C10—H10	108.1	C23—C24—C25	119.5 (3)
N2—C11—C21	110.4 (2)	C23—C24—H24	120.3
N2—C11—C12	111.9 (2)	C25—C24—H24	120.3
C21—C11—C12	110.9 (2)	C24—C25—C26	120.0 (3)
N2—C11—H11	107.8	C24—C25—H25	120.0
C21—C11—H11	107.8	C26—C25—H25	120.0
C12—C11—H11	107.8	C25—C26—C21	121.2 (3)
C8—C12—C13	113.6 (2)	C25—C26—H26	119.4
C8—C12—C11	108.7 (2)	C21—C26—H26	119.4
C7—O1—N1—C8	−175.3 (2)	N1—C8—C12—C11	−123.9 (3)
C6—C1—C2—C3	−1.4 (5)	C9—C8—C12—C11	54.0 (3)
Br1—C1—C2—C3	178.8 (2)	N2—C11—C12—C8	−53.8 (3)
C1—C2—C3—C4	0.5 (5)	C21—C11—C12—C8	−177.5 (2)
C2—C3—C4—C5	0.9 (5)	N2—C11—C12—C13	−179.6 (2)
C3—C4—C5—C6	−1.5 (5)	C21—C11—C12—C13	56.7 (3)
C4—C5—C6—C1	0.6 (4)	N2—C10—C15—C16	−138.9 (3)
C4—C5—C6—C7	179.6 (3)	C9—C10—C15—C16	97.3 (3)
C2—C1—C6—C5	0.9 (4)	N2—C10—C15—C20	44.5 (4)
Br1—C1—C6—C5	−179.3 (2)	C9—C10—C15—C20	−79.3 (3)
C2—C1—C6—C7	−178.2 (3)	C20—C15—C16—C17	−0.6 (5)
Br1—C1—C6—C7	1.7 (4)	C10—C15—C16—C17	−177.2 (3)
N1—O1—C7—C6	−171.7 (2)	C15—C16—C17—C18	−0.5 (5)
C5—C6—C7—O1	−5.5 (4)	C16—C17—C18—C19	0.8 (5)
C1—C6—C7—O1	173.5 (2)	C17—C18—C19—C20	0.0 (5)
O1—N1—C8—C9	2.3 (4)	C18—C19—C20—C15	−1.2 (5)
O1—N1—C8—C12	179.8 (2)	C16—C15—C20—C19	1.4 (5)
N1—C8—C9—C10	122.8 (3)	C10—C15—C20—C19	178.0 (3)
C12—C8—C9—C10	−54.8 (3)	N2—C11—C21—C22	−72.3 (3)
C14—N2—C10—C15	61.1 (3)	C12—C11—C21—C22	52.3 (3)
C11—N2—C10—C15	−179.4 (2)	N2—C11—C21—C26	107.5 (3)
C14—N2—C10—C9	−176.3 (2)	C12—C11—C21—C26	−127.9 (3)
C11—N2—C10—C9	−56.8 (3)	C26—C21—C22—C23	−0.2 (4)
C8—C9—C10—N2	54.5 (3)	C11—C21—C22—C23	179.6 (3)
C8—C9—C10—C15	178.7 (2)	C21—C22—C23—C24	−0.7 (4)
C14—N2—C11—C21	−59.2 (3)	C22—C23—C24—C25	1.0 (4)
C10—N2—C11—C21	−179.0 (2)	C23—C24—C25—C26	−0.4 (4)
C14—N2—C11—C12	176.7 (2)	C24—C25—C26—C21	−0.5 (4)
C10—N2—C11—C12	56.9 (3)	C22—C21—C26—C25	0.8 (4)
N1—C8—C12—C13	0.5 (4)	C11—C21—C26—C25	−179.0 (3)
C9—C8—C12—C13	178.3 (3)

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

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

Symmetry code: (i) .