2,6-Bis(3-methoxy-phen-yl)-3-methyl-piperidin-4-one.

In the mol-ecule of the title compound, C(20)H(23)NO(3), the bulky methoxy-phenyl substituents at the equatorial 2,6-positions crowd the vicinity of the equatorial amino H atom and prevent it from forming inter-molecular hydrogen bonds. The piperidine ring adopts a distorted chair conformation.

Related literature

For the crystal structure of a related piperidinone compound, see: Nithya et al. (2009 ▶).

Experimental

Crystal data

C20H23NO3

M = 325.39

Monoclinic,

a = 28.695 (3) Å

b = 10.9717 (12) Å

c = 11.3946 (13) Å

β = 95.078 (2)°

V = 3573.3 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 290 K

0.35 × 0.12 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: none

12581 measured reflections

3148 independent reflections

1751 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.154

S = 1.04

3148 reflections

224 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (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: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809045346/ci2955sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045346/ci2955Isup2.hkl

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

C20H23NO3	F(000) = 1392
Mr = 325.39	Dx = 1.210 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1065 reflections
a = 28.695 (3) Å	θ = 2.0–20.8°
b = 10.9717 (12) Å	µ = 0.08 mm−1
c = 11.3946 (13) Å	T = 290 K
β = 95.078 (2)°	Plate, colourless
V = 3573.3 (7) Å3	0.35 × 0.12 × 0.08 mm
Z = 8

Bruker SMART CCD area-detector diffractometer	1751 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.058
graphite	θmax = 25.0°, θmin = 1.4°
φ and ω scans	h = −33→34
12581 measured reflections	k = −13→11
3148 independent reflections	l = −13→13

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0658P)2 + 0.6442P] where P = (Fo2 + 2Fc2)/3
3148 reflections	(Δ/σ)max = 0.001
224 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.58419 (9)	0.8518 (2)	0.9145 (2)	0.1002 (10)
O2	0.76371 (8)	0.5426 (2)	0.51929 (18)	0.0750 (7)
O3	0.57121 (8)	0.17943 (18)	1.10361 (17)	0.0647 (6)
N1	0.65515 (8)	0.5548 (2)	0.83450 (19)	0.0438 (6)
H1N	0.6737 (9)	0.493 (2)	0.850 (2)	0.042 (8)*
C1	0.68070 (10)	0.6693 (3)	0.8526 (2)	0.0460 (7)
H1	0.6910	0.6772	0.9366	0.055*
C2	0.64767 (11)	0.7743 (3)	0.8172 (3)	0.0585 (9)
H2A	0.6627	0.8505	0.8419	0.070*
H2B	0.6420	0.7760	0.7320	0.070*
C3	0.60185 (12)	0.7651 (3)	0.8696 (3)	0.0588 (9)
C4	0.57864 (10)	0.6416 (3)	0.8627 (2)	0.0488 (8)
H4	0.5697	0.6251	0.7792	0.059*
C5	0.61533 (9)	0.5452 (2)	0.9056 (2)	0.0405 (7)
H5	0.6262	0.5630	0.9878	0.049*
C6	0.59593 (9)	0.4172 (2)	0.8989 (2)	0.0392 (7)
C7	0.59208 (9)	0.3507 (2)	1.0002 (2)	0.0429 (7)
H7	0.6019	0.3850	1.0729	0.051*
C8	0.57388 (10)	0.2338 (3)	0.9957 (2)	0.0456 (7)
C9	0.56020 (11)	0.1801 (3)	0.8898 (3)	0.0573 (8)
H9	0.5487	0.1009	0.8864	0.069*
C10	0.56400 (11)	0.2471 (3)	0.7879 (3)	0.0646 (9)
H10	0.5544	0.2123	0.7153	0.078*
C11	0.58152 (10)	0.3632 (3)	0.7912 (2)	0.0525 (8)
H11	0.5838	0.4061	0.7216	0.063*
C12	0.72330 (10)	0.6733 (3)	0.7837 (2)	0.0445 (7)
C13	0.72600 (10)	0.6065 (3)	0.6817 (2)	0.0500 (8)
H13	0.7013	0.5558	0.6550	0.060*
C14	0.76509 (11)	0.6143 (3)	0.6189 (3)	0.0549 (8)
C15	0.80184 (12)	0.6882 (3)	0.6568 (3)	0.0686 (10)
H15	0.8284	0.6922	0.6155	0.082*
C16	0.79871 (12)	0.7568 (3)	0.7577 (3)	0.0716 (10)
H16	0.8232	0.8085	0.7834	0.086*
C17	0.76009 (11)	0.7498 (3)	0.8206 (3)	0.0597 (9)
H17	0.7587	0.7967	0.8882	0.072*
C18	0.80099 (13)	0.5566 (3)	0.4451 (3)	0.0848 (12)
H18A	0.8021	0.6396	0.4189	0.127*
H18B	0.7958	0.5036	0.3782	0.127*
H18C	0.8301	0.5359	0.4885	0.127*
C19	0.55104 (15)	0.0625 (3)	1.1084 (3)	0.0877 (12)
H19A	0.5192	0.0654	1.0746	0.132*
H19B	0.5518	0.0365	1.1890	0.132*
H19C	0.5684	0.0060	1.0650	0.132*
C20	0.53454 (12)	0.6374 (3)	0.9252 (3)	0.0826 (11)
H20A	0.5421	0.6511	1.0079	0.124*
H20B	0.5201	0.5589	0.9136	0.124*
H20C	0.5134	0.6994	0.8939	0.124*

	U11	U22	U33	U12	U13	U23
O1	0.119 (2)	0.0536 (16)	0.135 (2)	0.0140 (15)	0.0511 (19)	−0.0246 (15)
O2	0.0798 (17)	0.0788 (16)	0.0713 (14)	−0.0245 (13)	0.0343 (13)	−0.0180 (13)
O3	0.0959 (17)	0.0445 (13)	0.0538 (13)	−0.0223 (12)	0.0074 (11)	0.0049 (10)
N1	0.0422 (15)	0.0342 (15)	0.0560 (15)	0.0009 (13)	0.0100 (12)	0.0041 (12)
C1	0.0515 (19)	0.0455 (18)	0.0403 (15)	−0.0075 (16)	0.0001 (14)	−0.0005 (13)
C2	0.069 (2)	0.0394 (19)	0.068 (2)	−0.0052 (16)	0.0137 (17)	−0.0052 (15)
C3	0.071 (2)	0.042 (2)	0.064 (2)	0.0102 (18)	0.0113 (17)	−0.0019 (15)
C4	0.0485 (19)	0.051 (2)	0.0485 (17)	0.0065 (16)	0.0123 (14)	−0.0005 (14)
C5	0.0421 (17)	0.0418 (17)	0.0381 (14)	−0.0016 (14)	0.0074 (12)	−0.0017 (12)
C6	0.0373 (16)	0.0382 (17)	0.0431 (16)	0.0028 (13)	0.0092 (13)	−0.0022 (13)
C7	0.0485 (18)	0.0393 (18)	0.0410 (16)	−0.0024 (14)	0.0049 (13)	−0.0036 (13)
C8	0.0482 (19)	0.0446 (19)	0.0447 (16)	−0.0016 (15)	0.0075 (13)	−0.0012 (14)
C9	0.068 (2)	0.0440 (19)	0.060 (2)	−0.0164 (16)	0.0096 (16)	−0.0051 (15)
C10	0.086 (3)	0.060 (2)	0.0469 (18)	−0.019 (2)	0.0026 (16)	−0.0138 (16)
C11	0.063 (2)	0.055 (2)	0.0407 (17)	−0.0082 (17)	0.0069 (14)	−0.0025 (14)
C12	0.0453 (18)	0.0438 (17)	0.0438 (16)	−0.0059 (15)	0.0006 (14)	0.0074 (13)
C13	0.0480 (19)	0.0487 (19)	0.0536 (18)	−0.0162 (15)	0.0067 (15)	−0.0026 (14)
C14	0.057 (2)	0.053 (2)	0.0560 (19)	−0.0118 (17)	0.0130 (16)	0.0019 (16)
C15	0.060 (2)	0.077 (2)	0.072 (2)	−0.019 (2)	0.0216 (18)	0.0035 (19)
C16	0.062 (2)	0.077 (2)	0.077 (2)	−0.032 (2)	0.0088 (19)	−0.002 (2)
C17	0.061 (2)	0.064 (2)	0.0535 (18)	−0.0187 (19)	0.0034 (16)	−0.0029 (16)
C18	0.089 (3)	0.094 (3)	0.077 (2)	−0.020 (2)	0.042 (2)	−0.012 (2)
C19	0.140 (4)	0.054 (2)	0.071 (2)	−0.031 (2)	0.021 (2)	0.0032 (18)
C20	0.074 (3)	0.076 (3)	0.103 (3)	0.017 (2)	0.039 (2)	0.011 (2)

O1—C3	1.212 (3)	C9—C10	1.388 (4)
O2—C14	1.379 (3)	C9—H9	0.93
O2—C18	1.429 (3)	C10—C11	1.368 (4)
O3—C8	1.375 (3)	C10—H10	0.93
O3—C19	1.411 (3)	C11—H11	0.93
N1—C1	1.460 (3)	C12—C13	1.382 (4)
N1—C5	1.462 (3)	C12—C17	1.384 (4)
N1—H1N	0.87 (3)	C13—C14	1.385 (4)
C1—C12	1.511 (4)	C13—H13	0.93
C1—C2	1.524 (4)	C14—C15	1.369 (4)
C1—H1	0.98	C15—C16	1.384 (4)
C2—C3	1.495 (4)	C15—H15	0.93
C2—H2A	0.97	C16—C17	1.374 (4)
C2—H2B	0.97	C16—H16	0.93
C3—C4	1.509 (4)	C17—H17	0.93
C4—C20	1.507 (4)	C18—H18A	0.96
C4—C5	1.541 (4)	C18—H18B	0.96
C4—H4	0.98	C18—H18C	0.96
C5—C6	1.511 (3)	C19—H19A	0.96
C5—H5	0.98	C19—H19B	0.96
C6—C7	1.379 (3)	C19—H19C	0.96
C6—C11	1.392 (3)	C20—H20A	0.96
C7—C8	1.384 (4)	C20—H20B	0.96
C7—H7	0.93	C20—H20C	0.96
C8—C9	1.368 (4)
C14—O2—C18	117.2 (2)	C10—C9—H9	120.9
C8—O3—C19	119.0 (2)	C11—C10—C9	121.7 (3)
C1—N1—C5	113.0 (2)	C11—C10—H10	119.2
C1—N1—H1N	110.2 (17)	C9—C10—H10	119.2
C5—N1—H1N	109.0 (16)	C10—C11—C6	120.0 (3)
N1—C1—C12	111.8 (2)	C10—C11—H11	120.0
N1—C1—C2	108.7 (2)	C6—C11—H11	120.0
C12—C1—C2	110.7 (2)	C13—C12—C17	118.6 (3)
N1—C1—H1	108.5	C13—C12—C1	122.0 (3)
C12—C1—H1	108.5	C17—C12—C1	119.4 (3)
C2—C1—H1	108.5	C12—C13—C14	120.6 (3)
C3—C2—C1	113.0 (2)	C12—C13—H13	119.7
C3—C2—H2A	109.0	C14—C13—H13	119.7
C1—C2—H2A	109.0	C15—C14—O2	124.2 (3)
C3—C2—H2B	109.0	C15—C14—C13	120.7 (3)
C1—C2—H2B	109.0	O2—C14—C13	115.1 (3)
H2A—C2—H2B	107.8	C14—C15—C16	118.6 (3)
O1—C3—C2	122.1 (3)	C14—C15—H15	120.7
O1—C3—C4	121.8 (3)	C16—C15—H15	120.7
C2—C3—C4	116.1 (3)	C17—C16—C15	121.2 (3)
C20—C4—C3	112.9 (3)	C17—C16—H16	119.4
C20—C4—C5	114.0 (2)	C15—C16—H16	119.4
C3—C4—C5	108.3 (2)	C16—C17—C12	120.3 (3)
C20—C4—H4	107.1	C16—C17—H17	119.9
C3—C4—H4	107.1	C12—C17—H17	119.9
C5—C4—H4	107.1	O2—C18—H18A	109.5
N1—C5—C6	110.0 (2)	O2—C18—H18B	109.5
N1—C5—C4	108.7 (2)	H18A—C18—H18B	109.5
C6—C5—C4	112.6 (2)	O2—C18—H18C	109.5
N1—C5—H5	108.5	H18A—C18—H18C	109.5
C6—C5—H5	108.5	H18B—C18—H18C	109.5
C4—C5—H5	108.5	O3—C19—H19A	109.5
C7—C6—C11	118.3 (3)	O3—C19—H19B	109.5
C7—C6—C5	120.4 (2)	H19A—C19—H19B	109.5
C11—C6—C5	121.3 (2)	O3—C19—H19C	109.5
C6—C7—C8	121.1 (3)	H19A—C19—H19C	109.5
C6—C7—H7	119.4	H19B—C19—H19C	109.5
C8—C7—H7	119.4	C4—C20—H20A	109.5
C9—C8—O3	124.5 (3)	C4—C20—H20B	109.5
C9—C8—C7	120.7 (3)	H20A—C20—H20B	109.5
O3—C8—C7	114.8 (2)	C4—C20—H20C	109.5
C8—C9—C10	118.2 (3)	H20A—C20—H20C	109.5
C8—C9—H9	120.9	H20B—C20—H20C	109.5
C5—N1—C1—C12	176.5 (2)	C6—C7—C8—C9	1.5 (4)
C5—N1—C1—C2	−61.0 (3)	C6—C7—C8—O3	−178.7 (2)
N1—C1—C2—C3	48.7 (3)	O3—C8—C9—C10	178.6 (3)
C12—C1—C2—C3	171.8 (2)	C7—C8—C9—C10	−1.6 (4)
C1—C2—C3—O1	134.6 (3)	C8—C9—C10—C11	1.0 (5)
C1—C2—C3—C4	−45.8 (4)	C9—C10—C11—C6	−0.2 (5)
O1—C3—C4—C20	−4.6 (4)	C7—C6—C11—C10	0.1 (4)
C2—C3—C4—C20	175.7 (3)	C5—C6—C11—C10	−179.9 (3)
O1—C3—C4—C5	−131.9 (3)	N1—C1—C12—C13	26.1 (4)
C2—C3—C4—C5	48.5 (3)	C2—C1—C12—C13	−95.1 (3)
C1—N1—C5—C6	−170.0 (2)	N1—C1—C12—C17	−156.6 (3)
C1—N1—C5—C4	66.3 (3)	C2—C1—C12—C17	82.1 (3)
C20—C4—C5—N1	177.2 (3)	C17—C12—C13—C14	1.2 (4)
C3—C4—C5—N1	−56.3 (3)	C1—C12—C13—C14	178.5 (3)
C20—C4—C5—C6	55.1 (3)	C18—O2—C14—C15	−6.7 (5)
C3—C4—C5—C6	−178.3 (2)	C18—O2—C14—C13	173.8 (3)
N1—C5—C6—C7	124.1 (3)	C12—C13—C14—C15	0.1 (5)
C4—C5—C6—C7	−114.6 (3)	C12—C13—C14—O2	179.5 (3)
N1—C5—C6—C11	−56.0 (3)	O2—C14—C15—C16	179.3 (3)
C4—C5—C6—C11	65.4 (3)	C13—C14—C15—C16	−1.3 (5)
C11—C6—C7—C8	−0.7 (4)	C14—C15—C16—C17	1.2 (5)
C5—C6—C7—C8	179.2 (2)	C15—C16—C17—C12	0.0 (5)
C19—O3—C8—C9	−3.2 (4)	C13—C12—C17—C16	−1.2 (4)
C19—O3—C8—C7	177.0 (3)	C1—C12—C17—C16	−178.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O3i	0.97	2.45	3.170 (4)	131
C19—H19C···O1ii	0.96	2.48	3.392 (4)	159