3,5-Dimethyl-2,6-di-phenyl-piperidine.

In the title compound, C19H23N, the piperidine ring has a chair conformation. The phenyl rings are inclined to one another by 52.76 (16)°. One of the methyl substituents on the piperidine ring is axial while the other is equatorial, like the phenyl rings. In the crystal, mol-ecules are linked via C-H⋯π inter-actions, forming zigzag chains along [001].

Related literature

For the biological activity of piperidine derivatives, see: Parthiban et al. (2005 ▶, 2009a ▶,b ▶, 2011 ▶); Aridoss et al. (2007 ▶). For related structures, see: Aravindhan et al. (2009 ▶); Sugumar et al. (2013 ▶). For ring puckering analysis, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C19H23N

M = 265.38

Orthorhombic,

a = 10.1689 (8) Å

b = 43.141 (3) Å

c = 7.2658 (5) Å

V = 3187.5 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.06 mm−1

T = 293 K

0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.978, T max = 0.984

8658 measured reflections

3900 independent reflections

2652 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.216

S = 0.78

3900 reflections

181 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S160053681400470X/su2706sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681400470X/su2706Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681400470X/su2706Isup3.cml

CCDC reference: 989359

Additional supporting information: crystallographic information; 3D view; checkCIF report

C19H23N	Z = 8
Mr = 265.38	F(000) = 1152
Orthorhombic, Iba2	Dx = 1.106 Mg m−3
Hall symbol: I 2 -2 c	Mo Kα radiation, λ = 0.71073 Å
a = 10.1689 (8) Å	µ = 0.06 mm−1
b = 43.141 (3) Å	T = 293 K
c = 7.2658 (5) Å	Block, colourless
V = 3187.5 (4) Å3	0.35 × 0.30 × 0.25 mm

Bruker Kappa APEXII CCD diffractometer	3900 independent reflections
Radiation source: fine-focus sealed tube	2652 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
ω and φ scan	θmax = 28.3°, θmin = 0.9°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −9→13
Tmin = 0.978, Tmax = 0.984	k = −57→45
8658 measured reflections	l = −9→9

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.216	H-atom parameters constrained
S = 0.78	w = 1/[σ2(Fo2) + (0.2P)2] where P = (Fo2 + 2Fc2)/3
3900 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.22 e Å−3
1 restraint	Δρmin = −0.24 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
C1	0.2691 (3)	0.31401 (6)	0.3689 (4)	0.0682 (6)
H1	0.3282	0.3302	0.3853	0.082*
C2	0.2822 (3)	0.28735 (6)	0.4756 (5)	0.0776 (7)
H2	0.3496	0.2857	0.5614	0.093*
C3	0.1939 (3)	0.26338 (6)	0.4524 (5)	0.0800 (8)
H3	0.2025	0.2453	0.5211	0.096*
C4	0.0933 (3)	0.26627 (6)	0.3277 (4)	0.0763 (7)
H4	0.0329	0.2503	0.3138	0.092*
C5	0.0812 (2)	0.29289 (5)	0.2223 (3)	0.0661 (6)
H5	0.0121	0.2946	0.1391	0.079*
C6	0.1706 (2)	0.31695 (5)	0.2394 (3)	0.0562 (5)
C7	0.1597 (2)	0.34446 (5)	0.1132 (3)	0.0573 (5)
H7	0.0660	0.3479	0.0886	0.069*
C8	0.2284 (2)	0.33925 (6)	−0.0733 (3)	0.0670 (6)
H8	0.1847	0.3219	−0.1349	0.080*
C9	0.2068 (3)	0.36835 (7)	−0.1906 (4)	0.0779 (7)
H9A	0.2541	0.3660	−0.3058	0.093*
H9B	0.1140	0.3701	−0.2194	0.093*
C10	0.2518 (3)	0.39803 (6)	−0.0974 (4)	0.0702 (7)
H10	0.3471	0.3968	−0.0789	0.084*
C11	0.1862 (2)	0.40069 (5)	0.0914 (4)	0.0635 (6)
H11	0.0910	0.4027	0.0734	0.076*
C12	0.2343 (2)	0.42859 (5)	0.1987 (4)	0.0662 (6)
C13	0.1532 (3)	0.45364 (6)	0.2290 (6)	0.0918 (10)
H13	0.0681	0.4535	0.1821	0.110*
C14	0.1971 (4)	0.47910 (6)	0.3290 (8)	0.1080 (13)
H14	0.1413	0.4958	0.3498	0.130*
C15	0.3227 (4)	0.47958 (7)	0.3968 (6)	0.1008 (12)
H15	0.3521	0.4965	0.4651	0.121*
C16	0.4041 (4)	0.45530 (6)	0.3639 (5)	0.0914 (9)
H16	0.4902	0.4559	0.4070	0.110*
C17	0.3604 (3)	0.42965 (7)	0.2667 (4)	0.0780 (7)
H17	0.4168	0.4130	0.2474	0.094*
C18	0.2231 (5)	0.42606 (9)	−0.2189 (6)	0.1090 (12)
H18A	0.2522	0.4446	−0.1579	0.163*
H18B	0.1303	0.4274	−0.2414	0.163*
H18C	0.2688	0.4239	−0.3338	0.163*
C19	0.3720 (3)	0.33137 (7)	−0.0545 (5)	0.0794 (8)
H19A	0.4097	0.3285	−0.1745	0.119*
H19B	0.3813	0.3126	0.0154	0.119*
H19C	0.4167	0.3480	0.0075	0.119*
N1	0.21151 (19)	0.37261 (4)	0.1973 (3)	0.0599 (5)
H1A	0.2533	0.3727	0.3002	0.072*

	U11	U22	U33	U12	U13	U23
C1	0.0619 (13)	0.0621 (12)	0.0804 (17)	−0.0039 (9)	−0.0054 (12)	−0.0084 (12)
C2	0.0826 (18)	0.0710 (15)	0.0793 (18)	0.0082 (13)	−0.0061 (14)	−0.0033 (14)
C3	0.097 (2)	0.0625 (14)	0.0808 (18)	0.0029 (13)	0.0222 (16)	−0.0044 (13)
C4	0.0858 (17)	0.0669 (14)	0.0760 (16)	−0.0181 (12)	0.0179 (15)	−0.0179 (13)
C5	0.0602 (12)	0.0750 (13)	0.0630 (12)	−0.0131 (10)	0.0065 (11)	−0.0173 (11)
C6	0.0497 (10)	0.0601 (11)	0.0588 (11)	−0.0007 (8)	0.0057 (9)	−0.0152 (10)
C7	0.0464 (9)	0.0628 (11)	0.0628 (13)	−0.0018 (8)	−0.0011 (10)	−0.0086 (10)
C8	0.0657 (15)	0.0756 (14)	0.0598 (13)	−0.0068 (11)	0.0001 (11)	−0.0185 (11)
C9	0.0816 (16)	0.0959 (18)	0.0561 (13)	−0.0100 (14)	−0.0074 (12)	−0.0069 (13)
C10	0.0691 (14)	0.0829 (16)	0.0587 (14)	−0.0036 (12)	−0.0055 (11)	0.0032 (12)
C11	0.0549 (11)	0.0617 (13)	0.0740 (14)	0.0011 (9)	−0.0030 (12)	−0.0011 (11)
C12	0.0715 (14)	0.0552 (11)	0.0721 (15)	−0.0054 (10)	0.0068 (13)	−0.0006 (11)
C13	0.0821 (17)	0.0632 (14)	0.130 (3)	−0.0011 (12)	0.012 (2)	−0.0039 (17)
C14	0.126 (3)	0.0569 (15)	0.141 (3)	−0.0040 (16)	0.025 (3)	−0.0173 (19)
C15	0.132 (3)	0.0689 (18)	0.102 (2)	−0.0337 (18)	0.016 (2)	−0.0117 (17)
C16	0.099 (2)	0.0863 (18)	0.089 (2)	−0.0260 (16)	−0.0070 (18)	−0.0075 (15)
C17	0.0792 (16)	0.0765 (15)	0.0784 (17)	−0.0010 (13)	−0.0083 (14)	−0.0101 (13)
C18	0.138 (3)	0.107 (3)	0.081 (2)	−0.005 (2)	−0.019 (2)	0.026 (2)
C19	0.0694 (16)	0.0872 (17)	0.0817 (17)	0.0035 (13)	0.0160 (14)	−0.0152 (14)
N1	0.0650 (11)	0.0579 (10)	0.0569 (11)	−0.0023 (7)	−0.0026 (9)	−0.0064 (9)

C1—C6	1.380 (4)	C10—H10	0.9800
C1—C2	1.394 (4)	C11—N1	1.458 (3)
C1—H1	0.9300	C11—C12	1.516 (4)
C2—C3	1.380 (4)	C11—H11	0.9800
C2—H2	0.9300	C12—C17	1.374 (4)
C3—C4	1.372 (5)	C12—C13	1.378 (4)
C3—H3	0.9300	C13—C14	1.391 (5)
C4—C5	1.386 (4)	C13—H13	0.9300
C4—H4	0.9300	C14—C15	1.369 (6)
C5—C6	1.385 (3)	C14—H14	0.9300
C5—H5	0.9300	C15—C16	1.356 (5)
C6—C7	1.504 (3)	C15—H15	0.9300
C7—N1	1.458 (3)	C16—C17	1.386 (4)
C7—C8	1.541 (3)	C16—H16	0.9300
C7—H7	0.9800	C17—H17	0.9300
C8—C19	1.506 (4)	C18—H18A	0.9600
C8—C9	1.533 (4)	C18—H18B	0.9600
C8—H8	0.9800	C18—H18C	0.9600
C9—C10	1.519 (4)	C19—H19A	0.9600
C9—H9A	0.9700	C19—H19B	0.9600
C9—H9B	0.9700	C19—H19C	0.9600
C10—C18	1.525 (4)	N1—H1A	0.8600
C10—C11	1.530 (4)
C6—C1—C2	121.6 (2)	C11—C10—H10	108.2
C6—C1—H1	119.2	N1—C11—C12	109.3 (2)
C2—C1—H1	119.2	N1—C11—C10	109.5 (2)
C3—C2—C1	119.2 (3)	C12—C11—C10	112.3 (2)
C3—C2—H2	120.4	N1—C11—H11	108.5
C1—C2—H2	120.4	C12—C11—H11	108.5
C4—C3—C2	119.8 (3)	C10—C11—H11	108.5
C4—C3—H3	120.1	C17—C12—C13	118.4 (3)
C2—C3—H3	120.1	C17—C12—C11	120.8 (2)
C3—C4—C5	120.5 (2)	C13—C12—C11	120.8 (3)
C3—C4—H4	119.8	C12—C13—C14	120.7 (3)
C5—C4—H4	119.8	C12—C13—H13	119.7
C6—C5—C4	120.8 (2)	C14—C13—H13	119.7
C6—C5—H5	119.6	C15—C14—C13	120.0 (3)
C4—C5—H5	119.6	C15—C14—H14	120.0
C1—C6—C5	118.0 (2)	C13—C14—H14	120.0
C1—C6—C7	122.80 (19)	C16—C15—C14	119.6 (3)
C5—C6—C7	119.2 (2)	C16—C15—H15	120.2
N1—C7—C6	112.05 (18)	C14—C15—H15	120.2
N1—C7—C8	109.02 (19)	C15—C16—C17	120.7 (3)
C6—C7—C8	112.79 (19)	C15—C16—H16	119.6
N1—C7—H7	107.6	C17—C16—H16	119.6
C6—C7—H7	107.6	C12—C17—C16	120.6 (3)
C8—C7—H7	107.6	C12—C17—H17	119.7
C19—C8—C9	112.0 (2)	C16—C17—H17	119.7
C19—C8—C7	113.1 (2)	C10—C18—H18A	109.5
C9—C8—C7	107.7 (2)	C10—C18—H18B	109.5
C19—C8—H8	107.9	H18A—C18—H18B	109.5
C9—C8—H8	107.9	C10—C18—H18C	109.5
C7—C8—H8	107.9	H18A—C18—H18C	109.5
C10—C9—C8	113.5 (2)	H18B—C18—H18C	109.5
C10—C9—H9A	108.9	C8—C19—H19A	109.5
C8—C9—H9A	108.9	C8—C19—H19B	109.5
C10—C9—H9B	108.9	H19A—C19—H19B	109.5
C8—C9—H9B	108.9	C8—C19—H19C	109.5
H9A—C9—H9B	107.7	H19A—C19—H19C	109.5
C9—C10—C18	110.7 (3)	H19B—C19—H19C	109.5
C9—C10—C11	109.4 (2)	C11—N1—C7	114.0 (2)
C18—C10—C11	112.1 (3)	C11—N1—H1A	123.0
C9—C10—H10	108.2	C7—N1—H1A	123.0
C18—C10—H10	108.2
C6—C1—C2—C3	−0.5 (4)	C9—C10—C11—N1	54.0 (3)
C1—C2—C3—C4	−1.2 (5)	C18—C10—C11—N1	177.1 (2)
C2—C3—C4—C5	1.2 (4)	C9—C10—C11—C12	175.7 (2)
C3—C4—C5—C6	0.6 (4)	C18—C10—C11—C12	−61.2 (3)
C2—C1—C6—C5	2.2 (4)	N1—C11—C12—C17	52.2 (3)
C2—C1—C6—C7	−175.6 (2)	C10—C11—C12—C17	−69.6 (3)
C4—C5—C6—C1	−2.3 (3)	N1—C11—C12—C13	−128.4 (3)
C4—C5—C6—C7	175.7 (2)	C10—C11—C12—C13	109.8 (3)
C1—C6—C7—N1	−30.0 (3)	C17—C12—C13—C14	−1.2 (5)
C5—C6—C7—N1	152.2 (2)	C11—C12—C13—C14	179.4 (3)
C1—C6—C7—C8	93.5 (3)	C12—C13—C14—C15	0.7 (6)
C5—C6—C7—C8	−84.3 (2)	C13—C14—C15—C16	0.8 (7)
N1—C7—C8—C19	67.8 (3)	C14—C15—C16—C17	−1.8 (6)
C6—C7—C8—C19	−57.4 (3)	C13—C12—C17—C16	0.2 (5)
N1—C7—C8—C9	−56.5 (2)	C11—C12—C17—C16	179.6 (3)
C6—C7—C8—C9	178.34 (19)	C15—C16—C17—C12	1.3 (5)
C19—C8—C9—C10	−69.9 (3)	C12—C11—N1—C7	175.44 (19)
C7—C8—C9—C10	55.1 (3)	C10—C11—N1—C7	−61.1 (3)
C8—C9—C10—C18	−178.0 (3)	C6—C7—N1—C11	−171.69 (18)
C8—C9—C10—C11	−54.1 (3)	C8—C7—N1—C11	62.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cg1i	0.93	2.90	3.187 (2)	170
C18—H18C···Cg2ii	0.96	2.99	3.762 (5)	139

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of rings C1–C6 and C12–C17, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯Cg1i	0.93	2.90	3.187 (2)	170
C18—H18C⋯Cg2ii	0.96	2.99	3.762 (5)	139

Symmetry codes: (i) ; (ii) .