1,3-Dimethyl-2,6-diphenyl-piperidin-4-one.

In the title moleclue, C(19)H(21)NO, the 4-piperidone ring adopts a chair conformation in which the two benzene rings and the methyl group attached to C atoms all have equatorial orientations. In the crystal structure, centrosymmetric dimers are formed through weak inter-molecular C-H⋯O hydrogen bonds [the dihedral angle between the aromatic rings is 58.51 (5)°].

Related literature

For general background, see: Badorrey et al. (1999 ▶); Grishina et al. (1994 ▶); Nalanishi et al. (1974 ▶); Perumal et al. (2001 ▶); Ponnuswamy et al. (2002 ▶). For a related crystal structure, see: Gayathri et al. (2008 ▶). For the synthetis, see: Noller & Baliah (1948 ▶). For puckering and asymmetry parameters, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶, 1995 ▶).

Experimental

Crystal data

C19H21NO

M = 279.37

Triclinic,

a = 5.9201 (2) Å

b = 10.9749 (3) Å

c = 12.8247 (3) Å

α = 80.2961 (12)°

β = 86.673 (2)°

γ = 76.4499 (11)°

V = 798.30 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 290 (2) K

0.28 × 0.21 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.943, T max = 0.987

12316 measured reflections

3143 independent reflections

2446 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.116

S = 1.02

3143 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809003419/lh2761sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003419/lh2761Isup2.hkl

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

C19H21NO	Z = 2
Mr = 279.37	F(000) = 300
Triclinic, P1	Dx = 1.162 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9201 (2) Å	Cell parameters from 873 reflections
b = 10.9749 (3) Å	θ = 1.9–20.8°
c = 12.8247 (3) Å	µ = 0.07 mm−1
α = 80.2961 (12)°	T = 290 K
β = 86.673 (2)°	Block, colorless
γ = 76.4499 (11)°	0.28 × 0.21 × 0.18 mm
V = 798.30 (4) Å3

Bruker SMART CCD area-detector diffractometer	3143 independent reflections
Radiation source: fine-focus sealed tube	2446 reflections with I > 2σ(I)
graphite	Rint = 0.019
φ and ω scans	θmax = 26.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→7
Tmin = 0.943, Tmax = 0.987	k = −13→13
12316 measured reflections	l = −15→14

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0539P)2 + 0.1409P] where P = (Fo2 + 2Fc2)/3
3143 reflections	(Δ/σ)max < 0.001
192 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.14 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
N1	0.17010 (18)	0.40892 (9)	0.73876 (8)	0.0419 (3)
O1	0.25711 (17)	0.47960 (11)	1.03053 (7)	0.0615 (3)
C1	0.1134 (2)	0.54013 (12)	0.76264 (10)	0.0419 (3)
H1	−0.0457	0.5582	0.7916	0.050*
C2	0.2788 (3)	0.55376 (14)	0.84570 (11)	0.0532 (4)
H2A	0.4336	0.5475	0.8146	0.064*
H2B	0.2276	0.6370	0.8665	0.064*
C3	0.2882 (2)	0.45443 (14)	0.94154 (10)	0.0485 (3)
C4	0.3367 (3)	0.32119 (14)	0.91755 (11)	0.0532 (4)
H4	0.4923	0.3030	0.8850	0.064*
C5	0.1607 (2)	0.31444 (12)	0.83478 (10)	0.0432 (3)
H5	0.0040	0.3339	0.8661	0.052*
C6	0.2066 (2)	0.18211 (12)	0.80603 (10)	0.0467 (3)
C7	0.4060 (3)	0.13480 (14)	0.75020 (12)	0.0571 (4)
H7	0.5153	0.1837	0.7319	0.069*
C8	0.4446 (3)	0.01556 (15)	0.72124 (14)	0.0711 (5)
H8	0.5799	−0.0148	0.6840	0.085*
C9	0.2867 (4)	−0.05793 (15)	0.74677 (15)	0.0748 (5)
H9	0.3126	−0.1374	0.7261	0.090*
C10	0.0903 (4)	−0.01377 (16)	0.80298 (17)	0.0791 (5)
H10	−0.0170	−0.0639	0.8214	0.095*
C11	0.0495 (3)	0.10595 (15)	0.83308 (14)	0.0656 (4)
H11	−0.0846	0.1348	0.8717	0.079*
C12	0.1264 (2)	0.63589 (12)	0.66384 (10)	0.0428 (3)
C13	−0.0613 (3)	0.73494 (13)	0.63339 (12)	0.0536 (4)
H13	−0.1987	0.7419	0.6733	0.064*
C14	−0.0475 (3)	0.82404 (14)	0.54407 (13)	0.0658 (4)
H14	−0.1752	0.8902	0.5245	0.079*
C15	0.1535 (3)	0.81493 (15)	0.48471 (13)	0.0675 (5)
H15	0.1629	0.8751	0.4252	0.081*
C16	0.3413 (3)	0.71672 (17)	0.51319 (13)	0.0687 (5)
H16	0.4776	0.7101	0.4725	0.082*
C17	0.3284 (3)	0.62776 (15)	0.60201 (12)	0.0579 (4)
H17	0.4565	0.5616	0.6207	0.070*
C18	0.0031 (3)	0.39902 (14)	0.66175 (12)	0.0623 (4)
H18A	−0.1504	0.4132	0.6928	0.093*
H18B	0.0439	0.3158	0.6422	0.093*
H18C	0.0069	0.4616	0.5999	0.093*
C19	0.3365 (4)	0.22361 (19)	1.01678 (14)	0.0942 (7)
H19A	0.4369	0.2368	1.0679	0.141*
H19B	0.3910	0.1398	0.9993	0.141*
H19C	0.1814	0.2326	1.0458	0.141*

	U11	U22	U33	U12	U13	U23
N1	0.0505 (6)	0.0408 (5)	0.0341 (6)	−0.0089 (5)	−0.0065 (4)	−0.0056 (4)
O1	0.0534 (6)	0.0987 (8)	0.0390 (6)	−0.0236 (5)	0.0017 (4)	−0.0217 (5)
C1	0.0439 (7)	0.0439 (7)	0.0377 (7)	−0.0076 (5)	−0.0009 (5)	−0.0097 (5)
C2	0.0664 (9)	0.0558 (8)	0.0426 (8)	−0.0190 (7)	−0.0068 (6)	−0.0132 (6)
C3	0.0408 (7)	0.0708 (9)	0.0369 (7)	−0.0152 (6)	−0.0045 (5)	−0.0120 (6)
C4	0.0567 (8)	0.0602 (8)	0.0391 (7)	−0.0083 (7)	−0.0098 (6)	−0.0021 (6)
C5	0.0426 (7)	0.0471 (7)	0.0378 (7)	−0.0091 (5)	0.0007 (5)	−0.0032 (5)
C6	0.0483 (8)	0.0455 (7)	0.0437 (7)	−0.0102 (6)	−0.0050 (6)	0.0006 (6)
C7	0.0632 (9)	0.0483 (8)	0.0588 (9)	−0.0138 (7)	0.0082 (7)	−0.0069 (7)
C8	0.0846 (12)	0.0519 (9)	0.0729 (11)	−0.0073 (8)	0.0069 (9)	−0.0134 (8)
C9	0.0964 (14)	0.0446 (8)	0.0832 (12)	−0.0136 (9)	−0.0167 (10)	−0.0081 (8)
C10	0.0831 (13)	0.0558 (9)	0.1021 (14)	−0.0323 (9)	−0.0123 (11)	0.0036 (10)
C11	0.0572 (9)	0.0586 (9)	0.0795 (11)	−0.0193 (7)	0.0017 (8)	0.0004 (8)
C12	0.0511 (7)	0.0410 (6)	0.0388 (7)	−0.0118 (5)	−0.0038 (5)	−0.0105 (5)
C13	0.0614 (9)	0.0448 (7)	0.0522 (8)	−0.0046 (6)	−0.0024 (6)	−0.0112 (6)
C14	0.0908 (12)	0.0407 (7)	0.0607 (10)	−0.0037 (7)	−0.0145 (9)	−0.0052 (7)
C15	0.1055 (14)	0.0528 (9)	0.0486 (9)	−0.0318 (9)	−0.0065 (9)	0.0003 (7)
C16	0.0750 (11)	0.0822 (11)	0.0516 (9)	−0.0312 (9)	0.0058 (8)	−0.0018 (8)
C17	0.0536 (9)	0.0651 (9)	0.0509 (9)	−0.0106 (7)	0.0006 (6)	−0.0018 (7)
C18	0.0852 (11)	0.0505 (8)	0.0540 (9)	−0.0167 (7)	−0.0292 (8)	−0.0049 (7)
C19	0.146 (2)	0.0797 (12)	0.0527 (11)	−0.0258 (12)	−0.0310 (11)	0.0125 (9)

N1—C18	1.4711 (16)	C9—C10	1.365 (3)
N1—C5	1.4777 (15)	C9—H9	0.9300
N1—C1	1.4800 (15)	C10—C11	1.395 (2)
O1—C3	1.2128 (15)	C10—H10	0.9300
C1—C12	1.5145 (18)	C11—H11	0.9300
C1—C2	1.5363 (18)	C12—C13	1.3820 (19)
C1—H1	0.9800	C12—C17	1.390 (2)
C2—C3	1.493 (2)	C13—C14	1.387 (2)
C2—H2A	0.9700	C13—H13	0.9300
C2—H2B	0.9700	C14—C15	1.367 (2)
C3—C4	1.503 (2)	C14—H14	0.9300
C4—C19	1.519 (2)	C15—C16	1.372 (2)
C4—C5	1.5520 (18)	C15—H15	0.9300
C4—H4	0.9800	C16—C17	1.381 (2)
C5—C6	1.5175 (18)	C16—H16	0.9300
C5—H5	0.9800	C17—H17	0.9300
C6—C11	1.383 (2)	C18—H18A	0.9600
C6—C7	1.384 (2)	C18—H18B	0.9600
C7—C8	1.384 (2)	C18—H18C	0.9600
C7—H7	0.9300	C19—H19A	0.9600
C8—C9	1.364 (3)	C19—H19B	0.9600
C8—H8	0.9300	C19—H19C	0.9600
C18—N1—C5	109.46 (10)	C8—C9—C10	119.37 (16)
C18—N1—C1	108.63 (10)	C8—C9—H9	120.3
C5—N1—C1	111.85 (9)	C10—C9—H9	120.3
N1—C1—C12	111.33 (10)	C9—C10—C11	120.50 (16)
N1—C1—C2	110.45 (10)	C9—C10—H10	119.7
C12—C1—C2	109.68 (10)	C11—C10—H10	119.7
N1—C1—H1	108.4	C6—C11—C10	120.59 (16)
C12—C1—H1	108.4	C6—C11—H11	119.7
C2—C1—H1	108.4	C10—C11—H11	119.7
C3—C2—C1	112.04 (11)	C13—C12—C17	118.07 (13)
C3—C2—H2A	109.2	C13—C12—C1	120.95 (12)
C1—C2—H2A	109.2	C17—C12—C1	120.97 (12)
C3—C2—H2B	109.2	C12—C13—C14	120.86 (15)
C1—C2—H2B	109.2	C12—C13—H13	119.6
H2A—C2—H2B	107.9	C14—C13—H13	119.6
O1—C3—C2	122.76 (13)	C15—C14—C13	120.18 (15)
O1—C3—C4	123.25 (13)	C15—C14—H14	119.9
C2—C3—C4	113.99 (11)	C13—C14—H14	119.9
C3—C4—C19	112.28 (13)	C14—C15—C16	119.84 (15)
C3—C4—C5	108.87 (11)	C14—C15—H15	120.1
C19—C4—C5	112.70 (13)	C16—C15—H15	120.1
C3—C4—H4	107.6	C15—C16—C17	120.21 (16)
C19—C4—H4	107.6	C15—C16—H16	119.9
C5—C4—H4	107.6	C17—C16—H16	119.9
N1—C5—C6	110.17 (10)	C16—C17—C12	120.83 (14)
N1—C5—C4	110.93 (10)	C16—C17—H17	119.6
C6—C5—C4	110.79 (10)	C12—C17—H17	119.6
N1—C5—H5	108.3	N1—C18—H18A	109.5
C6—C5—H5	108.3	N1—C18—H18B	109.5
C4—C5—H5	108.3	H18A—C18—H18B	109.5
C11—C6—C7	117.95 (13)	N1—C18—H18C	109.5
C11—C6—C5	121.26 (13)	H18A—C18—H18C	109.5
C7—C6—C5	120.78 (12)	H18B—C18—H18C	109.5
C6—C7—C8	120.81 (15)	C4—C19—H19A	109.5
C6—C7—H7	119.6	C4—C19—H19B	109.5
C8—C7—H7	119.6	H19A—C19—H19B	109.5
C9—C8—C7	120.77 (17)	C4—C19—H19C	109.5
C9—C8—H8	119.6	H19A—C19—H19C	109.5
C7—C8—H8	119.6	H19B—C19—H19C	109.5
C18—N1—C1—C12	−59.74 (14)	N1—C5—C6—C7	55.01 (16)
C5—N1—C1—C12	179.33 (10)	C4—C5—C6—C7	−68.12 (16)
C18—N1—C1—C2	178.16 (11)	C11—C6—C7—C8	0.9 (2)
C5—N1—C1—C2	57.22 (13)	C5—C6—C7—C8	−178.08 (14)
N1—C1—C2—C3	−52.14 (15)	C6—C7—C8—C9	0.2 (3)
C12—C1—C2—C3	−175.21 (11)	C7—C8—C9—C10	−1.1 (3)
C1—C2—C3—O1	−127.65 (13)	C8—C9—C10—C11	0.8 (3)
C1—C2—C3—C4	51.65 (16)	C7—C6—C11—C10	−1.1 (2)
O1—C3—C4—C19	1.3 (2)	C5—C6—C11—C10	177.82 (14)
C2—C3—C4—C19	−178.02 (14)	C9—C10—C11—C6	0.3 (3)
O1—C3—C4—C5	126.78 (13)	N1—C1—C12—C13	124.49 (13)
C2—C3—C4—C5	−52.51 (15)	C2—C1—C12—C13	−112.96 (14)
C18—N1—C5—C6	56.39 (14)	N1—C1—C12—C17	−56.44 (15)
C1—N1—C5—C6	176.84 (10)	C2—C1—C12—C17	66.11 (15)
C18—N1—C5—C4	179.44 (11)	C17—C12—C13—C14	−0.4 (2)
C1—N1—C5—C4	−60.11 (13)	C1—C12—C13—C14	178.66 (12)
C3—C4—C5—N1	55.96 (14)	C12—C13—C14—C15	0.0 (2)
C19—C4—C5—N1	−178.79 (13)	C13—C14—C15—C16	0.5 (2)
C3—C4—C5—C6	178.65 (11)	C14—C15—C16—C17	−0.5 (2)
C19—C4—C5—C6	−56.09 (17)	C15—C16—C17—C12	0.0 (2)
N1—C5—C6—C11	−123.92 (14)	C13—C12—C17—C16	0.5 (2)
C4—C5—C6—C11	112.95 (15)	C1—C12—C17—C16	−178.65 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1i	0.98	2.56	3.3535 (16)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O1i	0.98	2.56	3.3535 (16)	139

Symmetry code: (i) .