3-Isopropyl-2,6-bis-(4-meth-oxy-phen-yl)-piperidin-4-one.

In the title compound, C(22)H(27)NO(3), the piperidine ring adopts a slightly distorted chair conformation. The dihedral angle between the two aromatic rings is 60.4 (1)°. In the crystal, the amino group forms a rather long N-H⋯O contact to a methoxy O atom. There are also C-H⋯O interactions present.

Related literature

For the biological activity of piperidine derivatives, see: Bochringer & n class="Chemical">Soehne (1961 ▶); El-Subbagh et al. (2000 ▶); Ganellin & Spickett (1965 ▶); Hagenbach & Gysin (1952 ▶); Jerom & Spencer (1988 ▶); Katritzky & Fan (1990 ▶); Perumal et al. (2001 ▶); Ravindran et al. (1991 ▶); Severs et al. (1965 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For asymmetry parameters, see: Nardelli (1983 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C22H27NO3

M = 353.45

Orthorhombic,

a = 7.5547 (3) Å

b = 11.8792 (6) Å

c = 22.1103 (10) Å

V = 1984.26 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEX CCD detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.983, T max = 0.986

10956 measured reflections

2801 independent reflections

1835 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.121

S = 1.03

2801 reflections

241 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.13 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536812030966/bt5928sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030966/bt5928Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812030966/bt5928Isup3.cml

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

C22H27NO3	F(000) = 760
Mr = 353.45	Dx = 1.183 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2938 reflections
a = 7.5547 (3) Å	θ = 1.8–28.3°
b = 11.8792 (6) Å	µ = 0.08 mm−1
c = 22.1103 (10) Å	T = 293 K
V = 1984.26 (16) Å3	Black, white crystalline
Z = 4	0.22 × 0.20 × 0.18 mm

Bruker SMART APEX CCD detector diffractometer	2801 independent reflections
Radiation source: fine-focus sealed tube	1835 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
ω scans	θmax = 28.3°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −10→9
Tmin = 0.983, Tmax = 0.986	k = −15→8
10956 measured reflections	l = −27→29

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0621P)2 + 0.0599P] where P = (Fo2 + 2Fc2)/3
2801 reflections	(Δ/σ)max = 0.015
241 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.13 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
H1	0.161 (4)	0.568 (2)	0.1225 (11)	0.049 (7)*
O1	0.3703 (3)	0.80940 (17)	−0.10981 (8)	0.0655 (6)
O2	0.6143 (3)	0.2871 (2)	0.15552 (10)	0.0773 (7)
O3	−0.2117 (3)	0.5919 (2)	0.37078 (10)	0.0865 (8)
N1	0.2620 (3)	0.53392 (18)	0.13369 (9)	0.0446 (5)
C2	0.3533 (3)	0.4891 (2)	0.08036 (10)	0.0433 (6)
H2	0.2910	0.4212	0.0669	0.052*
C3	0.5444 (3)	0.4554 (2)	0.09959 (11)	0.0451 (6)
H3	0.5993	0.5241	0.1155	0.054*
C4	0.5323 (4)	0.3749 (3)	0.15235 (13)	0.0556 (7)
C5	0.4118 (4)	0.4096 (3)	0.20247 (12)	0.0676 (9)
H5A	0.4656	0.4711	0.2247	0.081*
H5B	0.3966	0.3470	0.2302	0.081*
C6	0.2300 (3)	0.4469 (2)	0.17908 (12)	0.0507 (6)
H6	0.1737	0.3825	0.1592	0.061*
C7	0.3092 (5)	0.7822 (3)	−0.16890 (12)	0.0731 (9)
H7A	0.3785	0.7215	−0.1850	0.110*
H7B	0.3206	0.8469	−0.1946	0.110*
H7C	0.1872	0.7599	−0.1670	0.110*
C8	−0.3714 (6)	0.5342 (4)	0.38404 (18)	0.1054 (14)
H8A	−0.4477	0.5363	0.3493	0.158*
H8B	−0.4292	0.5699	0.4176	0.158*
H8C	−0.3453	0.4574	0.3941	0.158*
C9	0.3520 (3)	0.5733 (2)	0.02940 (10)	0.0413 (5)
C10	0.4059 (3)	0.6843 (2)	0.03831 (12)	0.0508 (6)
H10	0.4390	0.7076	0.0768	0.061*
C11	0.4112 (4)	0.7599 (2)	−0.00879 (13)	0.0555 (7)
H11	0.4486	0.8333	−0.0019	0.067*
C12	0.3614 (3)	0.7275 (2)	−0.06612 (11)	0.0470 (6)
C13	0.3080 (4)	0.6181 (2)	−0.07623 (11)	0.0518 (7)
H13	0.2749	0.5950	−0.1148	0.062*
C14	0.3041 (3)	0.5433 (2)	−0.02846 (11)	0.0493 (6)
H14	0.2676	0.4697	−0.0357	0.059*
C15	0.6625 (3)	0.4165 (2)	0.04695 (12)	0.0470 (6)
H15	0.6556	0.4757	0.0162	0.056*
C16	0.8571 (3)	0.4099 (3)	0.06599 (13)	0.0578 (7)
H16A	0.8910	0.4792	0.0851	0.087*
H16B	0.9296	0.3976	0.0309	0.087*
H16C	0.8728	0.3488	0.0939	0.087*
C17	0.6047 (4)	0.3087 (3)	0.01612 (14)	0.0691 (8)
H17A	0.4828	0.3150	0.0043	0.104*
H17B	0.6181	0.2467	0.0436	0.104*
H17C	0.6765	0.2961	−0.0191	0.104*
C18	0.1107 (3)	0.4866 (2)	0.22900 (11)	0.0489 (6)
C19	−0.0469 (3)	0.4320 (2)	0.24044 (12)	0.0521 (6)
H19	−0.0796	0.3720	0.2159	0.063*
C20	−0.1579 (4)	0.4634 (3)	0.28710 (12)	0.0577 (7)
H20	−0.2627	0.4243	0.2939	0.069*
C21	−0.1124 (4)	0.5531 (3)	0.32367 (12)	0.0579 (7)
C22	0.0451 (4)	0.6089 (3)	0.31305 (13)	0.0625 (8)
H22	0.0774	0.6689	0.3377	0.075*
C23	0.1547 (4)	0.5767 (2)	0.26643 (13)	0.0577 (7)
H23	0.2597	0.6156	0.2598	0.069*

	U11	U22	U33	U12	U13	U23
O1	0.0953 (15)	0.0511 (11)	0.0502 (11)	−0.0043 (11)	0.0027 (10)	0.0050 (9)
O2	0.0696 (13)	0.0697 (14)	0.0927 (15)	0.0253 (12)	0.0052 (11)	0.0272 (12)
O3	0.0879 (16)	0.1049 (19)	0.0665 (14)	−0.0023 (15)	0.0205 (12)	−0.0176 (13)
N1	0.0394 (10)	0.0469 (13)	0.0475 (12)	0.0030 (10)	−0.0020 (9)	0.0051 (10)
C2	0.0364 (10)	0.0433 (14)	0.0503 (13)	−0.0006 (10)	−0.0025 (10)	0.0002 (11)
C3	0.0401 (11)	0.0420 (14)	0.0532 (14)	0.0022 (10)	−0.0056 (11)	0.0021 (13)
C4	0.0427 (13)	0.0603 (18)	0.0638 (17)	0.0085 (13)	−0.0080 (12)	0.0113 (15)
C5	0.0638 (17)	0.085 (2)	0.0543 (16)	0.0188 (17)	−0.0014 (14)	0.0201 (16)
C6	0.0504 (13)	0.0529 (16)	0.0487 (14)	0.0018 (12)	0.0016 (11)	0.0082 (13)
C7	0.108 (2)	0.068 (2)	0.0435 (16)	0.0003 (19)	0.0086 (17)	0.0070 (15)
C8	0.096 (3)	0.137 (4)	0.083 (2)	−0.012 (3)	0.038 (2)	−0.014 (2)
C9	0.0333 (10)	0.0407 (14)	0.0499 (14)	0.0004 (10)	−0.0019 (10)	−0.0008 (11)
C10	0.0588 (15)	0.0479 (16)	0.0457 (14)	−0.0043 (13)	−0.0080 (12)	−0.0018 (13)
C11	0.0693 (17)	0.0400 (15)	0.0572 (16)	−0.0103 (13)	−0.0047 (14)	−0.0029 (13)
C12	0.0519 (13)	0.0414 (16)	0.0478 (14)	0.0024 (12)	0.0057 (11)	0.0012 (12)
C13	0.0661 (16)	0.0472 (16)	0.0420 (14)	0.0008 (12)	−0.0071 (12)	−0.0036 (12)
C14	0.0567 (14)	0.0383 (14)	0.0529 (15)	−0.0021 (11)	−0.0056 (12)	−0.0028 (12)
C15	0.0413 (11)	0.0454 (14)	0.0543 (14)	0.0048 (11)	−0.0024 (11)	−0.0031 (12)
C16	0.0431 (13)	0.0596 (18)	0.0706 (18)	0.0027 (12)	−0.0004 (13)	−0.0089 (15)
C17	0.0547 (16)	0.0677 (19)	0.085 (2)	0.0008 (15)	−0.0062 (15)	−0.0205 (17)
C18	0.0478 (13)	0.0529 (16)	0.0461 (13)	0.0025 (12)	−0.0039 (11)	0.0104 (13)
C19	0.0509 (13)	0.0556 (16)	0.0498 (14)	−0.0027 (13)	−0.0045 (12)	0.0008 (13)
C20	0.0513 (13)	0.073 (2)	0.0485 (14)	−0.0068 (14)	0.0014 (12)	0.0042 (14)
C21	0.0625 (15)	0.0669 (19)	0.0443 (14)	0.0046 (14)	0.0016 (13)	0.0002 (14)
C22	0.0728 (18)	0.0581 (19)	0.0566 (17)	−0.0064 (15)	−0.0047 (15)	−0.0039 (15)
C23	0.0561 (15)	0.0556 (17)	0.0615 (17)	−0.0095 (14)	−0.0029 (13)	0.0068 (14)

O1—C12	1.373 (3)	C10—C11	1.376 (4)
O1—C7	1.423 (3)	C10—H10	0.9300
O2—C4	1.215 (3)	C11—C12	1.377 (4)
O3—C21	1.364 (3)	C11—H11	0.9300
O3—C8	1.419 (5)	C12—C13	1.379 (4)
N1—C6	1.461 (3)	C13—C14	1.381 (4)
N1—C2	1.466 (3)	C13—H13	0.9300
N1—H1	0.90 (3)	C14—H14	0.9300
C2—C9	1.507 (3)	C15—C17	1.515 (4)
C2—C3	1.557 (3)	C15—C16	1.531 (3)
C2—H2	0.9800	C15—H15	0.9800
C3—C4	1.512 (4)	C16—H16A	0.9600
C3—C15	1.538 (3)	C16—H16B	0.9600
C3—H3	0.9800	C16—H16C	0.9600
C4—C5	1.493 (4)	C17—H17A	0.9600
C5—C6	1.533 (4)	C17—H17B	0.9600
C5—H5A	0.9700	C17—H17C	0.9600
C5—H5B	0.9700	C18—C19	1.380 (4)
C6—C18	1.501 (4)	C18—C23	1.392 (4)
C6—H6	0.9800	C19—C20	1.381 (4)
C7—H7A	0.9600	C19—H19	0.9300
C7—H7B	0.9600	C20—C21	1.382 (4)
C7—H7C	0.9600	C20—H20	0.9300
C8—H8A	0.9600	C21—C22	1.382 (4)
C8—H8B	0.9600	C22—C23	1.377 (4)
C8—H8C	0.9600	C22—H22	0.9300
C9—C14	1.377 (3)	C23—H23	0.9300
C9—C10	1.393 (4)
C12—O1—C7	118.0 (2)	C9—C10—H10	119.4
C21—O3—C8	117.5 (3)	C10—C11—C12	120.4 (3)
C6—N1—C2	111.9 (2)	C10—C11—H11	119.8
C6—N1—H1	111.7 (16)	C12—C11—H11	119.8
C2—N1—H1	109.9 (16)	O1—C12—C11	115.9 (2)
N1—C2—C9	110.95 (19)	O1—C12—C13	124.6 (2)
N1—C2—C3	108.06 (19)	C11—C12—C13	119.5 (2)
C9—C2—C3	112.40 (18)	C12—C13—C14	119.3 (2)
N1—C2—H2	108.4	C12—C13—H13	120.4
C9—C2—H2	108.4	C14—C13—H13	120.4
C3—C2—H2	108.4	C9—C14—C13	122.6 (2)
C4—C3—C15	115.4 (2)	C9—C14—H14	118.7
C4—C3—C2	108.5 (2)	C13—C14—H14	118.7
C15—C3—C2	114.1 (2)	C17—C15—C16	111.0 (2)
C4—C3—H3	106.0	C17—C15—C3	115.3 (2)
C15—C3—H3	106.0	C16—C15—C3	111.4 (2)
C2—C3—H3	106.0	C17—C15—H15	106.2
O2—C4—C5	120.4 (3)	C16—C15—H15	106.2
O2—C4—C3	123.9 (3)	C3—C15—H15	106.2
C5—C4—C3	115.8 (2)	C15—C16—H16A	109.5
C4—C5—C6	112.1 (2)	C15—C16—H16B	109.5
C4—C5—H5A	109.2	H16A—C16—H16B	109.5
C6—C5—H5A	109.2	C15—C16—H16C	109.5
C4—C5—H5B	109.2	H16A—C16—H16C	109.5
C6—C5—H5B	109.2	H16B—C16—H16C	109.5
H5A—C5—H5B	107.9	C15—C17—H17A	109.5
N1—C6—C18	112.5 (2)	C15—C17—H17B	109.5
N1—C6—C5	106.8 (2)	H17A—C17—H17B	109.5
C18—C6—C5	112.4 (2)	C15—C17—H17C	109.5
N1—C6—H6	108.4	H17A—C17—H17C	109.5
C18—C6—H6	108.4	H17B—C17—H17C	109.5
C5—C6—H6	108.4	C19—C18—C23	117.3 (2)
O1—C7—H7A	109.5	C19—C18—C6	120.4 (2)
O1—C7—H7B	109.5	C23—C18—C6	122.4 (2)
H7A—C7—H7B	109.5	C18—C19—C20	122.3 (3)
O1—C7—H7C	109.5	C18—C19—H19	118.9
H7A—C7—H7C	109.5	C20—C19—H19	118.9
H7B—C7—H7C	109.5	C19—C20—C21	119.6 (3)
O3—C8—H8A	109.5	C19—C20—H20	120.2
O3—C8—H8B	109.5	C21—C20—H20	120.2
H8A—C8—H8B	109.5	O3—C21—C22	116.2 (3)
O3—C8—H8C	109.5	O3—C21—C20	124.8 (3)
H8A—C8—H8C	109.5	C22—C21—C20	119.0 (3)
H8B—C8—H8C	109.5	C23—C22—C21	120.8 (3)
C14—C9—C10	117.0 (2)	C23—C22—H22	119.6
C14—C9—C2	121.6 (2)	C21—C22—H22	119.6
C10—C9—C2	121.3 (2)	C22—C23—C18	121.0 (3)
C11—C10—C9	121.3 (2)	C22—C23—H23	119.5
C11—C10—H10	119.4	C18—C23—H23	119.5
C6—N1—C2—C9	168.49 (19)	C10—C11—C12—C13	−0.7 (4)
C6—N1—C2—C3	−67.9 (2)	O1—C12—C13—C14	−179.8 (2)
N1—C2—C3—C4	54.9 (3)	C11—C12—C13—C14	0.5 (4)
C9—C2—C3—C4	177.7 (2)	C10—C9—C14—C13	−0.1 (4)
N1—C2—C3—C15	−174.9 (2)	C2—C9—C14—C13	−177.6 (2)
C9—C2—C3—C15	−52.1 (3)	C12—C13—C14—C9	−0.1 (4)
C15—C3—C4—O2	3.0 (4)	C4—C3—C15—C17	61.6 (3)
C2—C3—C4—O2	132.5 (3)	C2—C3—C15—C17	−65.1 (3)
C15—C3—C4—C5	−177.4 (2)	C4—C3—C15—C16	−66.0 (3)
C2—C3—C4—C5	−47.9 (3)	C2—C3—C15—C16	167.3 (2)
O2—C4—C5—C6	−131.9 (3)	N1—C6—C18—C19	120.8 (3)
C3—C4—C5—C6	48.5 (4)	C5—C6—C18—C19	−118.7 (3)
C2—N1—C6—C18	−170.4 (2)	N1—C6—C18—C23	−61.0 (3)
C2—N1—C6—C5	65.9 (3)	C5—C6—C18—C23	59.5 (3)
C4—C5—C6—N1	−53.8 (3)	C23—C18—C19—C20	−0.5 (4)
C4—C5—C6—C18	−177.6 (3)	C6—C18—C19—C20	177.9 (2)
N1—C2—C9—C14	−131.8 (2)	C18—C19—C20—C21	0.7 (4)
C3—C2—C9—C14	107.1 (3)	C8—O3—C21—C22	−178.0 (3)
N1—C2—C9—C10	50.7 (3)	C8—O3—C21—C20	1.6 (5)
C3—C2—C9—C10	−70.4 (3)	C19—C20—C21—O3	179.7 (3)
C14—C9—C10—C11	−0.2 (4)	C19—C20—C21—C22	−0.8 (4)
C2—C9—C10—C11	177.4 (2)	O3—C21—C22—C23	−179.7 (3)
C9—C10—C11—C12	0.6 (4)	C20—C21—C22—C23	0.7 (4)
C7—O1—C12—C11	−175.9 (3)	C21—C22—C23—C18	−0.5 (4)
C7—O1—C12—C13	4.4 (4)	C19—C18—C23—C22	0.4 (4)
C10—C11—C12—O1	179.6 (2)	C6—C18—C23—C22	−177.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.90 (2)	2.66 (2)	3.538 (2)	167.4 (17)
C16—H16A···O1ii	0.96	2.57	3.474 (4)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.90 (2)	2.66 (2)	3.538 (2)	167.4 (17)
C16—H16A⋯O1ii	0.96	2.57	3.474 (4)	156

Symmetry codes: (i) ; (ii) .