c-3,t-3-Dimethyl-r-2,c-6-diphenyl-piperidin-4-one.

In the title compound, C(19)H(21)NO, the piperidine ring adopts a chair conformation. The two phenyl rings attached to the piperidine ring at 2 and 6 positions occupy equatorial orientations and the dihedral angle between them is 57.53 (11)°. In the crystal, the mol-ecules are connected via weak inter-molecular C-H⋯π inter-actions, leading to a zigzag chains.

Related literature

For general background to piperidine derivatives, see: Badorrey et al. (1999 ▶); Nalanishi et al. (1974 ▶); Elena et al. (2002 ▶). For hybridization, see: Beddoes et al. (1986 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For ring conformational analysis, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶). For the synthesis of the title compound, see Noller & Baliah (1948 ▶).

Experimental

Crystal data

C19H21NO

M = 279.37

Triclinic,

a = 6.0293 (4) Å

b = 10.8198 (6) Å

c = 12.1649 (6) Å

α = 98.559 (2)°

β = 92.836 (3)°

γ = 96.677 (3)°

V = 777.62 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 293 K

0.20 × 0.20 × 0.18 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.986, T max = 0.987

15310 measured reflections

3556 independent reflections

1930 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.168

S = 1.06

3556 reflections

197 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809041580/bt5058sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041580/bt5058Isup2.hkl

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

C19H21NO	Z = 2
Mr = 279.37	F(000) = 300
Triclinic, P1	Dx = 1.193 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.0293 (4) Å	Cell parameters from 3556 reflections
b = 10.8198 (6) Å	θ = 1.7–28.2°
c = 12.1649 (6) Å	µ = 0.07 mm−1
α = 98.559 (2)°	T = 293 K
β = 92.836 (3)°	Block, colourless
γ = 96.677 (3)°	0.20 × 0.20 × 0.18 mm
V = 777.62 (8) Å3

Bruker Kappa APEXII area-detector diffractometer	3556 independent reflections
Radiation source: fine-focus sealed tube	1930 reflections with I > 2σ(I)
graphite	Rint = 0.036
ω and φ scans	θmax = 28.2°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −8→7
Tmin = 0.986, Tmax = 0.987	k = −14→13
15310 measured reflections	l = −15→15

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)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.168	w = 1/[σ2(Fo2) + (0.0729P)2 + 0.1205P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.014
3556 reflections	Δρmax = 0.18 e Å−3
197 parameters	Δρmin = −0.19 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.020 (5)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C2	0.1988 (3)	0.24655 (18)	0.32290 (15)	0.0425 (5)
H2	0.0400	0.2403	0.3379	0.051*
C3	0.3320 (3)	0.22876 (19)	0.43103 (15)	0.0468 (5)
C4	0.2694 (3)	0.0952 (2)	0.45372 (16)	0.0493 (5)
C5	0.2448 (4)	−0.00903 (19)	0.35615 (16)	0.0524 (6)
H5A	0.1674	−0.0845	0.3778	0.063*
H5B	0.3923	−0.0271	0.3353	0.063*
C6	0.1161 (3)	0.02397 (18)	0.25591 (15)	0.0442 (5)
H6	−0.0376	0.0336	0.2750	0.053*
C7	0.2596 (3)	0.37123 (18)	0.28453 (15)	0.0455 (5)
C8	0.1269 (4)	0.4668 (2)	0.30562 (18)	0.0588 (6)
H8	0.0030	0.4548	0.3472	0.071*
C9	0.1733 (5)	0.5791 (2)	0.2668 (2)	0.0723 (7)
H9	0.0818	0.6421	0.2825	0.087*
C10	0.3532 (5)	0.5982 (2)	0.2053 (2)	0.0750 (8)
H10	0.3836	0.6738	0.1781	0.090*
C11	0.4897 (5)	0.5055 (2)	0.18330 (19)	0.0704 (7)
H11	0.6138	0.5187	0.1421	0.084*
C12	0.4420 (4)	0.3928 (2)	0.22252 (17)	0.0551 (6)
H12	0.5344	0.3301	0.2069	0.066*
C13	0.2732 (5)	0.3230 (2)	0.52803 (18)	0.0740 (8)
H13A	0.1152	0.3097	0.5367	0.111*
H13B	0.3139	0.4072	0.5133	0.111*
H13C	0.3535	0.3117	0.5952	0.111*
C14	0.5846 (4)	0.2435 (2)	0.41959 (19)	0.0644 (7)
H14A	0.6588	0.2207	0.4839	0.097*
H14B	0.6361	0.3294	0.4137	0.097*
H14C	0.6176	0.1895	0.3540	0.097*
C15	0.1096 (4)	−0.07639 (18)	0.15558 (16)	0.0460 (5)
C16	0.2873 (4)	−0.0837 (2)	0.08964 (18)	0.0605 (6)
H16	0.4134	−0.0243	0.1061	0.073*
C17	0.2818 (5)	−0.1775 (2)	−0.0003 (2)	0.0728 (7)
H17	0.4041	−0.1810	−0.0438	0.087*
C18	0.0987 (5)	−0.2653 (2)	−0.0261 (2)	0.0726 (7)
H18	0.0952	−0.3285	−0.0872	0.087*
C19	−0.0791 (5)	−0.2598 (2)	0.0383 (2)	0.0732 (7)
H19	−0.2041	−0.3199	0.0214	0.088*
C20	−0.0753 (4)	−0.1654 (2)	0.12890 (19)	0.0620 (6)
H20	−0.1982	−0.1621	0.1720	0.074*
N1	0.2245 (3)	0.14438 (15)	0.23353 (13)	0.0435 (4)
O1	0.2492 (3)	0.07213 (16)	0.54724 (12)	0.0687 (5)
H1	0.168 (4)	0.1575 (19)	0.1717 (19)	0.058 (7)*

	U11	U22	U33	U12	U13	U23
C2	0.0418 (11)	0.0477 (12)	0.0367 (10)	0.0071 (9)	0.0038 (8)	0.0012 (8)
C3	0.0453 (12)	0.0570 (13)	0.0363 (10)	0.0018 (9)	0.0019 (8)	0.0053 (9)
C4	0.0431 (12)	0.0697 (15)	0.0359 (11)	0.0030 (10)	0.0002 (8)	0.0143 (10)
C5	0.0626 (14)	0.0528 (13)	0.0438 (11)	0.0061 (10)	0.0021 (10)	0.0155 (10)
C6	0.0457 (12)	0.0475 (12)	0.0408 (10)	0.0046 (9)	0.0043 (8)	0.0118 (9)
C7	0.0534 (13)	0.0460 (12)	0.0343 (10)	0.0066 (9)	−0.0041 (8)	−0.0013 (8)
C8	0.0655 (16)	0.0525 (14)	0.0571 (13)	0.0139 (11)	−0.0024 (11)	0.0016 (11)
C9	0.093 (2)	0.0524 (15)	0.0708 (16)	0.0209 (13)	−0.0092 (15)	0.0045 (12)
C10	0.113 (2)	0.0494 (15)	0.0612 (15)	0.0044 (15)	−0.0152 (15)	0.0155 (12)
C11	0.094 (2)	0.0629 (16)	0.0531 (14)	−0.0037 (14)	0.0060 (12)	0.0151 (12)
C12	0.0680 (15)	0.0488 (13)	0.0489 (12)	0.0079 (11)	0.0092 (10)	0.0065 (10)
C13	0.096 (2)	0.0789 (17)	0.0410 (12)	0.0077 (14)	−0.0001 (12)	−0.0051 (12)
C14	0.0462 (14)	0.0788 (17)	0.0677 (15)	−0.0021 (12)	−0.0080 (10)	0.0215 (13)
C15	0.0554 (13)	0.0428 (11)	0.0402 (10)	0.0039 (9)	−0.0023 (9)	0.0113 (9)
C16	0.0711 (16)	0.0504 (13)	0.0572 (14)	0.0011 (11)	0.0117 (12)	0.0015 (11)
C17	0.096 (2)	0.0644 (16)	0.0565 (14)	0.0135 (14)	0.0155 (13)	−0.0003 (12)
C18	0.110 (2)	0.0549 (14)	0.0486 (14)	0.0124 (15)	−0.0144 (11)	0.0005 (11)
C19	0.0874 (18)	0.0583 (15)	0.0652 (15)	−0.0101 (13)	−0.0227 (10)	0.0058 (12)
C20	0.0625 (15)	0.0627 (15)	0.0569 (14)	−0.0055 (12)	−0.0061 (11)	0.0103 (11)
N1	0.0562 (11)	0.0423 (10)	0.0321 (9)	0.0055 (8)	0.0016 (7)	0.0071 (7)
O1	0.0743 (11)	0.0921 (12)	0.0396 (8)	−0.0042 (9)	0.0012 (7)	0.0223 (8)

C2—N1	1.458 (2)	C10—H10	0.9300
C2—C7	1.504 (3)	C11—C12	1.380 (3)
C2—C3	1.555 (3)	C11—H11	0.9300
C2—H2	0.9800	C12—H12	0.9300
C3—C4	1.520 (3)	C13—H13A	0.9600
C3—C13	1.525 (3)	C13—H13B	0.9600
C3—C14	1.528 (3)	C13—H13C	0.9600
C4—O1	1.209 (2)	C14—H14A	0.9600
C4—C5	1.499 (3)	C14—H14B	0.9600
C5—C6	1.522 (3)	C14—H14C	0.9600
C5—H5A	0.9700	C15—C16	1.372 (3)
C5—H5B	0.9700	C15—C20	1.377 (3)
C6—N1	1.457 (2)	C16—C17	1.372 (3)
C6—C15	1.504 (3)	C16—H16	0.9300
C6—H6	0.9800	C17—C18	1.362 (4)
C7—C12	1.381 (3)	C17—H17	0.9300
C7—C8	1.382 (3)	C18—C19	1.360 (4)
C8—C9	1.371 (3)	C18—H18	0.9300
C8—H8	0.9300	C19—C20	1.383 (3)
C9—C10	1.361 (4)	C19—H19	0.9300
C9—H9	0.9300	C20—H20	0.9300
C10—C11	1.374 (4)	N1—H1	0.85 (2)
N1—C2—C7	109.70 (15)	C10—C11—C12	119.8 (2)
N1—C2—C3	109.78 (16)	C10—C11—H11	120.1
C7—C2—C3	114.76 (15)	C12—C11—H11	120.1
N1—C2—H2	107.4	C11—C12—C7	121.2 (2)
C7—C2—H2	107.4	C11—C12—H12	119.4
C3—C2—H2	107.4	C7—C12—H12	119.4
C4—C3—C13	109.95 (17)	C3—C13—H13A	109.5
C4—C3—C14	106.01 (17)	C3—C13—H13B	109.5
C13—C3—C14	110.43 (18)	H13A—C13—H13B	109.5
C4—C3—C2	108.99 (15)	C3—C13—H13C	109.5
C13—C3—C2	109.16 (18)	H13A—C13—H13C	109.5
C14—C3—C2	112.25 (16)	H13B—C13—H13C	109.5
O1—C4—C5	120.6 (2)	C3—C14—H14A	109.5
O1—C4—C3	121.75 (19)	C3—C14—H14B	109.5
C5—C4—C3	117.57 (16)	H14A—C14—H14B	109.5
C4—C5—C6	112.35 (17)	C3—C14—H14C	109.5
C4—C5—H5A	109.1	H14A—C14—H14C	109.5
C6—C5—H5A	109.1	H14B—C14—H14C	109.5
C4—C5—H5B	109.1	C16—C15—C20	118.2 (2)
C6—C5—H5B	109.1	C16—C15—C6	121.47 (18)
H5A—C5—H5B	107.9	C20—C15—C6	120.3 (2)
N1—C6—C15	111.07 (15)	C17—C16—C15	121.0 (2)
N1—C6—C5	107.32 (16)	C17—C16—H16	119.5
C15—C6—C5	111.89 (17)	C15—C16—H16	119.5
N1—C6—H6	108.8	C18—C17—C16	120.4 (2)
C15—C6—H6	108.8	C18—C17—H17	119.8
C5—C6—H6	108.8	C16—C17—H17	119.8
C12—C7—C8	117.4 (2)	C17—C18—C19	119.4 (2)
C12—C7—C2	121.77 (19)	C17—C18—H18	120.3
C8—C7—C2	120.70 (19)	C19—C18—H18	120.3
C9—C8—C7	121.6 (2)	C18—C19—C20	120.5 (2)
C9—C8—H8	119.2	C18—C19—H19	119.8
C7—C8—H8	119.2	C20—C19—H19	119.8
C10—C9—C8	120.0 (3)	C15—C20—C19	120.4 (2)
C10—C9—H9	120.0	C15—C20—H20	119.8
C8—C9—H9	120.0	C19—C20—H20	119.8
C9—C10—C11	119.9 (2)	C6—N1—C2	111.51 (15)
C9—C10—H10	120.0	C6—N1—H1	107.9 (14)
C11—C10—H10	120.0	C2—N1—H1	111.3 (15)
N1—C2—C3—C4	−50.7 (2)	C7—C8—C9—C10	0.4 (4)
C7—C2—C3—C4	−174.77 (16)	C8—C9—C10—C11	−0.8 (4)
N1—C2—C3—C13	−170.78 (17)	C9—C10—C11—C12	0.8 (4)
C7—C2—C3—C13	65.1 (2)	C10—C11—C12—C7	−0.5 (3)
N1—C2—C3—C14	66.4 (2)	C8—C7—C12—C11	0.0 (3)
C7—C2—C3—C14	−57.6 (2)	C2—C7—C12—C11	176.84 (19)
C13—C3—C4—O1	−22.3 (3)	N1—C6—C15—C16	39.6 (3)
C14—C3—C4—O1	97.1 (2)	C5—C6—C15—C16	−80.3 (2)
C2—C3—C4—O1	−141.9 (2)	N1—C6—C15—C20	−141.7 (2)
C13—C3—C4—C5	160.91 (19)	C5—C6—C15—C20	98.4 (2)
C14—C3—C4—C5	−79.7 (2)	C20—C15—C16—C17	−0.3 (3)
C2—C3—C4—C5	41.3 (2)	C6—C15—C16—C17	178.5 (2)
O1—C4—C5—C6	139.4 (2)	C15—C16—C17—C18	0.2 (4)
C3—C4—C5—C6	−43.7 (2)	C16—C17—C18—C19	−0.3 (4)
C4—C5—C6—N1	53.0 (2)	C17—C18—C19—C20	0.5 (4)
C4—C5—C6—C15	175.09 (16)	C16—C15—C20—C19	0.5 (3)
N1—C2—C7—C12	−41.6 (2)	C6—C15—C20—C19	−178.3 (2)
C3—C2—C7—C12	82.6 (2)	C18—C19—C20—C15	−0.6 (4)
N1—C2—C7—C8	135.14 (19)	C15—C6—N1—C2	170.45 (16)
C3—C2—C7—C8	−100.7 (2)	C5—C6—N1—C2	−67.0 (2)
C12—C7—C8—C9	0.0 (3)	C7—C2—N1—C6	−165.75 (16)
C2—C7—C8—C9	−176.82 (19)	C3—C2—N1—C6	67.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···Cg3i	0.93	2.95	3.648	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯Cg3i	0.93	2.95	3.648	133

Symmetry codes: (i) . Cg3 is the centroid of the C15–C20 ring.