Ethyl 3-methyl-2,6-diphenyl-piperidine-1-carboxyl-ate.

In the title compound, C(21)H(25)NO(2), the piperidine ring adopts a twisted boat conformation characterized by puckering parameters θ = 89.5 (1) and ϕ = 257.5 (2)°. The phenyl groups are located in equatorial and axial positions on the central piperidine ring, while the methyl group is in an equatorial position. The dihedral angle between the phenyl rings is 49.8 (1)°. An intra-molecular C-H⋯O inter-action occurs. The crystal structure features weak inter-molecular C-H⋯O inter-actions and a stabilizing inter-molecular C-H⋯π contact involving the axial phenyl ring.

Related literature

For the biological activity of related piperidines, see: Parthiban et al. (2009 ▶); Aridoss et al. (2007 ▶). For ring conformational analysis, see: Cremer & Pople (1975 ▶); Nardelli (1995 ▶). For the conformation of piperidine derivatives, see: Ravindran et al. (1991 ▶); Krishna Kumar & Krishna Pillay (1996 ▶). For the synthesis of the title compound, see: Sampath et al. (2003 ▶); Noller & Baliah (1948 ▶).

Experimental

Crystal data

C21H25NO2

M = 323.42

Monoclinic,

a = 10.4113 (3) Å

b = 10.6073 (6) Å

c = 16.2782 (6) Å

β = 95.960 (2)°

V = 1787.98 (13) Å3

Z = 4

Cu Kα radiation

μ = 0.60 mm−1

T = 293 K

0.26 × 0.22 × 0.18 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

3698 measured reflections

3502 independent reflections

2428 reflections with I > 2σ(I)

R int = 0.012

Standard reflections: 3; every 60 minutes intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.136

S = 1.03

3502 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms, 1996 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 and PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811019155/bh2353sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811019155/bh2353Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811019155/bh2353Isup3.cml

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

C21H25NO2	F(000) = 696
Mr = 323.42	Dx = 1.201 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 10.4113 (3) Å	θ = 0–90°
b = 10.6073 (6) Å	µ = 0.60 mm−1
c = 16.2782 (6) Å	T = 293 K
β = 95.960 (2)°	Needle, colourless
V = 1787.98 (13) Å3	0.26 × 0.22 × 0.18 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.012
Radiation source: fine-focus sealed tube	θmax = 72.0°, θmin = 4.8°
graphite	h = 0→12
ω scans	k = 0→13
3698 measured reflections	l = −20→19
3502 independent reflections	3 standard reflections every 60 min
2428 reflections with I > 2σ(I)	intensity decay: none

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045	H-atom parameters constrained
wR(F2) = 0.136	w = 1/[σ2(Fo2) + (0.0736P)2 + 0.2748P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
3502 reflections	Δρmax = 0.17 e Å−3
218 parameters	Δρmin = −0.20 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraints	Extinction coefficient: 0.0022 (4)
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
O1	0.92030 (13)	0.42372 (12)	0.12110 (7)	0.0586 (4)
O2	0.99447 (12)	0.61660 (11)	0.15872 (7)	0.0516 (3)
N1	0.90776 (13)	0.49725 (13)	0.25183 (8)	0.0427 (3)
C2	0.81474 (15)	0.39802 (16)	0.26812 (10)	0.0455 (4)
H2	0.7841	0.3620	0.2142	0.055*
C3	0.69751 (17)	0.45929 (18)	0.30030 (11)	0.0516 (4)
H3A	0.6370	0.3939	0.3123	0.062*
H3B	0.6550	0.5127	0.2574	0.062*
C4	0.73118 (18)	0.5382 (2)	0.37787 (12)	0.0584 (5)
H4A	0.7073	0.4918	0.4254	0.070*
H4B	0.6810	0.6153	0.3735	0.070*
C5	0.87457 (16)	0.57150 (17)	0.39184 (10)	0.0470 (4)
H5	0.9212	0.4975	0.4155	0.056*
C6	0.92925 (15)	0.60452 (16)	0.30998 (9)	0.0414 (4)
H6	0.8820	0.6777	0.2857	0.050*
C7	1.07053 (16)	0.63999 (16)	0.32679 (9)	0.0435 (4)
C8	1.16351 (18)	0.55226 (19)	0.35314 (13)	0.0587 (5)
H8	1.1416	0.4675	0.3555	0.070*
C9	1.2899 (2)	0.5901 (2)	0.37612 (15)	0.0718 (6)
H9	1.3516	0.5301	0.3942	0.086*
C10	1.3249 (2)	0.7134 (2)	0.37269 (14)	0.0680 (6)
H10	1.4095	0.7378	0.3888	0.082*
C11	1.2344 (2)	0.8007 (2)	0.34532 (14)	0.0686 (6)
H11	1.2576	0.8851	0.3421	0.082*
C12	1.10831 (19)	0.76434 (18)	0.32231 (12)	0.0563 (5)
H12	1.0477	0.8249	0.3034	0.068*
C13	0.87742 (17)	0.28998 (16)	0.31910 (10)	0.0459 (4)
C14	0.81423 (19)	0.22492 (19)	0.37698 (11)	0.0565 (5)
H14	0.7339	0.2528	0.3897	0.068*
C15	0.8691 (2)	0.1193 (2)	0.41592 (12)	0.0676 (6)
H15	0.8256	0.0768	0.4546	0.081*
C16	0.9876 (2)	0.0766 (2)	0.39778 (13)	0.0685 (6)
H16	1.0241	0.0051	0.4237	0.082*
C17	1.0513 (2)	0.1403 (2)	0.34120 (13)	0.0657 (5)
H17	1.1318	0.1121	0.3291	0.079*
C18	0.99719 (19)	0.24578 (18)	0.30200 (12)	0.0558 (5)
H18	1.0416	0.2879	0.2636	0.067*
C19	0.8953 (2)	0.6789 (2)	0.45370 (11)	0.0642 (5)
H19A	0.9856	0.6992	0.4622	0.096*
H19B	0.8659	0.6536	0.5052	0.096*
H19C	0.8476	0.7515	0.4328	0.096*
C20	0.93902 (16)	0.50599 (16)	0.17288 (10)	0.0440 (4)
C21	1.0362 (2)	0.6314 (2)	0.07700 (12)	0.0637 (5)
H21A	0.9644	0.6169	0.0351	0.076*
H21B	1.1039	0.5713	0.0688	0.076*
C22	1.0848 (3)	0.7612 (2)	0.07088 (15)	0.0802 (7)
H22A	1.1132	0.7740	0.0172	0.120*
H22B	1.1558	0.7744	0.1125	0.120*
H22C	1.0169	0.8199	0.0789	0.120*

	U11	U22	U33	U12	U13	U23
O1	0.0793 (9)	0.0536 (8)	0.0446 (7)	−0.0032 (7)	0.0148 (6)	−0.0103 (6)
O2	0.0663 (8)	0.0519 (7)	0.0388 (6)	−0.0084 (6)	0.0165 (5)	0.0009 (5)
N1	0.0506 (8)	0.0425 (7)	0.0355 (7)	−0.0050 (6)	0.0076 (6)	−0.0007 (6)
C2	0.0476 (9)	0.0477 (9)	0.0408 (8)	−0.0065 (7)	0.0024 (7)	0.0012 (7)
C3	0.0453 (9)	0.0592 (11)	0.0500 (10)	−0.0015 (8)	0.0038 (7)	0.0055 (8)
C4	0.0522 (10)	0.0690 (13)	0.0566 (11)	−0.0021 (9)	0.0179 (8)	−0.0046 (9)
C5	0.0513 (9)	0.0530 (10)	0.0378 (8)	−0.0001 (8)	0.0095 (7)	−0.0017 (7)
C6	0.0464 (9)	0.0409 (8)	0.0376 (8)	0.0002 (7)	0.0068 (6)	−0.0019 (6)
C7	0.0476 (9)	0.0451 (9)	0.0386 (8)	−0.0019 (7)	0.0077 (7)	−0.0015 (7)
C8	0.0526 (11)	0.0519 (11)	0.0712 (12)	−0.0010 (9)	0.0048 (9)	0.0060 (9)
C9	0.0508 (11)	0.0749 (15)	0.0881 (16)	0.0031 (10)	0.0001 (10)	0.0103 (12)
C10	0.0519 (11)	0.0813 (15)	0.0705 (13)	−0.0152 (11)	0.0052 (9)	−0.0012 (11)
C11	0.0689 (13)	0.0583 (12)	0.0788 (14)	−0.0205 (11)	0.0080 (11)	−0.0033 (11)
C12	0.0594 (11)	0.0460 (10)	0.0630 (11)	−0.0039 (9)	0.0044 (9)	−0.0018 (8)
C13	0.0528 (9)	0.0429 (9)	0.0414 (8)	−0.0076 (7)	0.0023 (7)	−0.0010 (7)
C14	0.0594 (11)	0.0592 (11)	0.0507 (10)	−0.0094 (9)	0.0047 (8)	0.0073 (9)
C15	0.0900 (16)	0.0600 (12)	0.0514 (11)	−0.0104 (11)	0.0015 (10)	0.0136 (9)
C16	0.0953 (16)	0.0522 (12)	0.0539 (11)	0.0051 (11)	−0.0124 (11)	0.0025 (9)
C17	0.0695 (13)	0.0556 (12)	0.0705 (13)	0.0114 (10)	0.0005 (10)	−0.0046 (10)
C18	0.0613 (11)	0.0481 (10)	0.0591 (10)	0.0012 (9)	0.0116 (9)	−0.0002 (8)
C19	0.0748 (13)	0.0732 (14)	0.0466 (10)	−0.0042 (11)	0.0162 (9)	−0.0146 (9)
C20	0.0492 (9)	0.0448 (9)	0.0389 (8)	0.0021 (7)	0.0094 (7)	0.0016 (7)
C21	0.0800 (13)	0.0707 (13)	0.0445 (10)	−0.0055 (11)	0.0266 (9)	0.0037 (9)
C22	0.0898 (16)	0.0844 (16)	0.0706 (13)	−0.0249 (13)	0.0288 (12)	0.0115 (12)

O1—C20	1.2148 (19)	C10—C11	1.362 (3)
O2—C20	1.338 (2)	C10—H10	0.9300
O2—C21	1.4500 (19)	C11—C12	1.382 (3)
N1—C20	1.3612 (19)	C11—H11	0.9300
N1—C2	1.473 (2)	C12—H12	0.9300
N1—C6	1.482 (2)	C13—C18	1.387 (2)
C2—C13	1.522 (2)	C13—C14	1.388 (2)
C2—C3	1.523 (2)	C14—C15	1.382 (3)
C2—H2	0.9800	C14—H14	0.9300
C3—C4	1.525 (3)	C15—C16	1.375 (3)
C3—H3A	0.9700	C15—H15	0.9300
C3—H3B	0.9700	C16—C17	1.368 (3)
C4—C5	1.528 (2)	C16—H16	0.9300
C4—H4A	0.9700	C17—C18	1.379 (3)
C4—H4B	0.9700	C17—H17	0.9300
C5—C19	1.521 (2)	C18—H18	0.9300
C5—C6	1.543 (2)	C19—H19A	0.9600
C5—H5	0.9800	C19—H19B	0.9600
C6—C7	1.515 (2)	C19—H19C	0.9600
C6—H6	0.9800	C21—C22	1.474 (3)
C7—C8	1.379 (2)	C21—H21A	0.9700
C7—C12	1.381 (2)	C21—H21B	0.9700
C8—C9	1.389 (3)	C22—H22A	0.9600
C8—H8	0.9300	C22—H22B	0.9600
C9—C10	1.361 (3)	C22—H22C	0.9600
C9—H9	0.9300
C20—O2—C21	115.37 (14)	C10—C11—C12	120.3 (2)
C20—N1—C2	116.41 (13)	C10—C11—H11	119.9
C20—N1—C6	121.04 (13)	C12—C11—H11	119.9
C2—N1—C6	119.48 (12)	C7—C12—C11	121.33 (19)
N1—C2—C13	112.56 (13)	C7—C12—H12	119.3
N1—C2—C3	108.81 (14)	C11—C12—H12	119.3
C13—C2—C3	116.58 (14)	C18—C13—C14	117.88 (17)
N1—C2—H2	106.0	C18—C13—C2	119.25 (15)
C13—C2—H2	106.0	C14—C13—C2	122.56 (16)
C3—C2—H2	106.0	C15—C14—C13	120.83 (19)
C2—C3—C4	113.29 (15)	C15—C14—H14	119.6
C2—C3—H3A	108.9	C13—C14—H14	119.6
C4—C3—H3A	108.9	C16—C15—C14	120.4 (2)
C2—C3—H3B	108.9	C16—C15—H15	119.8
C4—C3—H3B	108.9	C14—C15—H15	119.8
H3A—C3—H3B	107.7	C17—C16—C15	119.4 (2)
C3—C4—C5	112.78 (14)	C17—C16—H16	120.3
C3—C4—H4A	109.0	C15—C16—H16	120.3
C5—C4—H4A	109.0	C16—C17—C18	120.6 (2)
C3—C4—H4B	109.0	C16—C17—H17	119.7
C5—C4—H4B	109.0	C18—C17—H17	119.7
H4A—C4—H4B	107.8	C17—C18—C13	120.92 (19)
C19—C5—C4	109.96 (15)	C17—C18—H18	119.5
C19—C5—C6	111.23 (15)	C13—C18—H18	119.5
C4—C5—C6	111.50 (14)	C5—C19—H19A	109.5
C19—C5—H5	108.0	C5—C19—H19B	109.5
C4—C5—H5	108.0	H19A—C19—H19B	109.5
C6—C5—H5	108.0	C5—C19—H19C	109.5
N1—C6—C7	112.66 (13)	H19A—C19—H19C	109.5
N1—C6—C5	109.43 (13)	H19B—C19—H19C	109.5
C7—C6—C5	109.80 (13)	O1—C20—O2	123.46 (15)
N1—C6—H6	108.3	O1—C20—N1	124.70 (16)
C7—C6—H6	108.3	O2—C20—N1	111.84 (14)
C5—C6—H6	108.3	O2—C21—C22	107.49 (17)
C8—C7—C12	117.81 (17)	O2—C21—H21A	110.2
C8—C7—C6	121.71 (16)	C22—C21—H21A	110.2
C12—C7—C6	120.28 (16)	O2—C21—H21B	110.2
C7—C8—C9	120.24 (19)	C22—C21—H21B	110.2
C7—C8—H8	119.9	H21A—C21—H21B	108.5
C9—C8—H8	119.9	C21—C22—H22A	109.5
C10—C9—C8	121.1 (2)	C21—C22—H22B	109.5
C10—C9—H9	119.4	H22A—C22—H22B	109.5
C8—C9—H9	119.4	C21—C22—H22C	109.5
C9—C10—C11	119.2 (2)	H22A—C22—H22C	109.5
C9—C10—H10	120.4	H22B—C22—H22C	109.5
C11—C10—H10	120.4
C20—N1—C2—C13	108.65 (16)	C8—C9—C10—C11	−0.8 (4)
C6—N1—C2—C13	−90.94 (17)	C9—C10—C11—C12	0.8 (3)
C20—N1—C2—C3	−120.56 (16)	C8—C7—C12—C11	−1.5 (3)
C6—N1—C2—C3	39.84 (19)	C6—C7—C12—C11	173.46 (16)
N1—C2—C3—C4	−57.33 (19)	C10—C11—C12—C7	0.4 (3)
C13—C2—C3—C4	71.2 (2)	N1—C2—C13—C18	−41.5 (2)
C2—C3—C4—C5	17.3 (2)	C3—C2—C13—C18	−168.23 (16)
C3—C4—C5—C19	163.67 (16)	N1—C2—C13—C14	145.07 (16)
C3—C4—C5—C6	39.8 (2)	C3—C2—C13—C14	18.3 (2)
C20—N1—C6—C7	−62.3 (2)	C18—C13—C14—C15	−0.2 (3)
C2—N1—C6—C7	138.25 (14)	C2—C13—C14—C15	173.29 (17)
C20—N1—C6—C5	175.28 (14)	C13—C14—C15—C16	−0.1 (3)
C2—N1—C6—C5	15.8 (2)	C14—C15—C16—C17	0.5 (3)
C19—C5—C6—N1	179.64 (15)	C15—C16—C17—C18	−0.5 (3)
C4—C5—C6—N1	−57.23 (19)	C16—C17—C18—C13	0.2 (3)
C19—C5—C6—C7	55.50 (19)	C14—C13—C18—C17	0.2 (3)
C4—C5—C6—C7	178.64 (15)	C2—C13—C18—C17	−173.55 (17)
N1—C6—C7—C8	−53.5 (2)	C21—O2—C20—O1	−2.2 (3)
C5—C6—C7—C8	68.8 (2)	C21—O2—C20—N1	177.33 (15)
N1—C6—C7—C12	131.73 (16)	C2—N1—C20—O1	−17.4 (2)
C5—C6—C7—C12	−106.04 (18)	C6—N1—C20—O1	−177.46 (16)
C12—C7—C8—C9	1.6 (3)	C2—N1—C20—O2	163.14 (14)
C6—C7—C8—C9	−173.36 (18)	C6—N1—C20—O2	3.1 (2)
C7—C8—C9—C10	−0.4 (3)	C20—O2—C21—C22	175.60 (17)

Cg1 is the centroid of the C13–C18 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1	0.98	2.28	2.749 (2)	109
C18—H18···O1	0.93	2.91	3.519 (2)	125
C14—H14···O2i	0.93	2.82	3.406 (2)	122
C10—H10···O1ii	0.93	2.67	3.460 (3)	144
C3—H3B···Cg1iii	0.97	2.70	3.666 (2)	172

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C13–C18 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯O1	0.93	2.91	3.519 (2)	125
C14—H14⋯O2i	0.93	2.82	3.406 (2)	122
C10—H10⋯O1ii	0.93	2.67	3.460 (3)	144
C3—H3B⋯Cg1iii	0.97	2.70	3.666 (2)	172

Symmetry codes: (i) ; (ii) ; (iii) .