r-2,c-6-Bis(3-methoxy-phen-yl)-t-3,t-5-dimethyl-piperidin-4-one.

In the title compound, C(21)H(25)NO(3), the piperidinone ring adopts a chair conformation with an equatorial orientation of all substituents; the 3-methoxy-phenyl groups make a dihedral angle of 60.26 (15)°. The carbonyl group O atom is disordered over two positions in a 0.643 (3):0.357 (3) ratio. The crystal structure is stabilized by N-H⋯O and C-H⋯O hydrogen bonding.

Related literature

For related literature, see: Angle et al. (1995 ▶); Balamurugan et al. (2008 ▶); Gayathri et al. (2008 ▶); Katritzky et al. (1990 ▶); Ramachandran et al. (2007 ▶); Thiruvalluvar et al. (2007 ▶; Cremer & Pople (1975 ▶); Noller & Baliah (1948 ▶).

Experimental

Crystal data

C21H25NO3

M = 339.42

Monoclinic,

a = 20.9885 (6) Å

b = 9.7699 (2) Å

c = 19.8153 (5) Å

β = 109.459 (2)°

V = 3831.14 (17) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 298 (2) K

0.25 × 0.23 × 0.22 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.931, T max = 0.983

23076 measured reflections

4624 independent reflections

2715 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.163

S = 0.92

4624 reflections

239 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.12 e Å−3

Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker–Nonius, 2004 ▶); cell refinement: APEX2; data reduction: SAINT-Plus (Bruker–Nonius, 2004 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808023490/bx2164sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023490/bx2164Isup2.hkl

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

C21H25NO3	F000 = 1456
Mr = 339.42	Dx = 1.177 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5862 reflections
a = 20.9885 (6) Å	θ = 2.4–22.6º
b = 9.7699 (2) Å	µ = 0.08 mm−1
c = 19.8153 (5) Å	T = 298 (2) K
β = 109.459 (2)º	Block, colourless
V = 3831.14 (17) Å3	0.25 × 0.23 × 0.22 mm
Z = 8

Bruker APEXII CCD area-detector diffractometer	4624 independent reflections
Radiation source: fine-focus sealed tube	2715 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.031
T = 298(2) K	θmax = 28.3º
φ and ω scans	θmin = 2.1º
Absorption correction: multi-scan(SADABS; Bruker, 1999)	h = −27→27
Tmin = 0.931, Tmax = 0.983	k = −13→12
23076 measured reflections	l = −26→23

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)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.163	w = 1/[σ2(Fo2) + (0.1P)2 + 0.5P] where P = (Fo2 + 2Fc2)/3
S = 0.92	(Δ/σ)max < 0.001
4624 reflections	Δρmax = 0.12 e Å−3
239 parameters	Δρmin = −0.14 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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 andgoodness of fit S are based on F2, conventional R-factors R are basedon F, with F set to zero for negative F2. The threshold expression ofF2 > σ(F2) is used only for calculating R-factors(gt) etc. and isnot relevant to the choice of reflections for refinement. R-factors basedon 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	Occ. (<1)
C1	0.34428 (7)	0.63001 (15)	0.18001 (8)	0.0440 (4)
H1	0.3033	0.6627	0.1881	0.053*
C2	0.32387 (8)	0.52388 (16)	0.11928 (8)	0.0477 (4)
H2	0.3651	0.4956	0.1101	0.057*
C3	0.29531 (8)	0.39913 (18)	0.14380 (9)	0.0548 (4)
C4	0.33555 (7)	0.33955 (15)	0.21586 (8)	0.0461 (4)
H4	0.3776	0.3020	0.2122	0.055*
C5	0.35427 (7)	0.45552 (15)	0.27161 (8)	0.0425 (4)
H5	0.3127	0.4922	0.2767	0.051*
C6	0.38064 (8)	0.75142 (15)	0.16328 (8)	0.0456 (4)
C7	0.44600 (8)	0.73763 (15)	0.16225 (8)	0.0445 (4)
H7	0.4668	0.6523	0.1703	0.053*
C8	0.48077 (8)	0.84985 (17)	0.14930 (8)	0.0499 (4)
C9	0.44996 (11)	0.97624 (18)	0.13621 (11)	0.0715 (6)
H9	0.4730	1.0519	0.1276	0.086*
C10	0.38482 (12)	0.9890 (2)	0.13608 (13)	0.0872 (7)
H10	0.3637	1.0740	0.1266	0.105*
C11	0.35003 (10)	0.87908 (19)	0.14962 (11)	0.0712 (6)
H11	0.3060	0.8902	0.1496	0.085*
C12	0.27530 (10)	0.5817 (2)	0.04956 (10)	0.0764 (6)
H12A	0.2658	0.5130	0.0129	0.115*
H12B	0.2955	0.6597	0.0353	0.115*
H12C	0.2340	0.6089	0.0566	0.115*
C13	0.29752 (10)	0.22367 (18)	0.23642 (11)	0.0678 (5)
H13A	0.2563	0.2582	0.2408	0.102*
H13B	0.3249	0.1853	0.2813	0.102*
H13C	0.2873	0.1541	0.2001	0.102*
C14	0.39959 (8)	0.40590 (15)	0.34391 (8)	0.0461 (4)
C15	0.37474 (10)	0.3865 (2)	0.39968 (10)	0.0731 (6)
H15	0.3298	0.4061	0.3934	0.088*
C16	0.41662 (12)	0.3379 (3)	0.46462 (11)	0.0924 (8)
H16	0.3991	0.3236	0.5014	0.111*
C17	0.48319 (11)	0.3104 (2)	0.47607 (10)	0.0742 (6)
H17	0.5109	0.2784	0.5203	0.089*
C18	0.50881 (8)	0.33063 (16)	0.42127 (8)	0.0516 (4)
C19	0.46682 (7)	0.37783 (15)	0.35542 (8)	0.0453 (4)
H19	0.4843	0.3908	0.3185	0.054*
C20	0.58679 (12)	0.9383 (3)	0.14770 (15)	0.0956 (7)
H20A	0.5679	0.9847	0.1027	0.143*
H20B	0.6315	0.9069	0.1527	0.143*
H20C	0.5889	1.0000	0.1860	0.143*
C21	0.62095 (10)	0.2629 (2)	0.49353 (11)	0.0866 (7)
H21A	0.6201	0.3258	0.5305	0.130*
H21B	0.6657	0.2595	0.4907	0.130*
H21C	0.6082	0.1734	0.5045	0.130*
H1A	0.4028 (8)	0.6278 (19)	0.2787 (10)	0.056 (5)*
N1	0.38767 (6)	0.56426 (13)	0.24572 (7)	0.0424 (3)
O1	0.54531 (6)	0.82403 (13)	0.15007 (6)	0.0624 (4)
O2A	0.2376 (3)	0.3574 (6)	0.1104 (2)	0.0878 (14)	0.760 (15)
O2B	0.2601 (7)	0.3246 (17)	0.1015 (7)	0.0878 (14)	0.241 (15)
O3	0.57452 (6)	0.30761 (13)	0.42644 (6)	0.0666 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0379 (8)	0.0520 (8)	0.0419 (9)	0.0083 (6)	0.0128 (7)	0.0066 (7)
C2	0.0397 (8)	0.0609 (10)	0.0385 (8)	−0.0020 (7)	0.0078 (7)	0.0035 (7)
C3	0.0445 (9)	0.0689 (11)	0.0451 (10)	−0.0112 (8)	0.0068 (8)	−0.0042 (8)
C4	0.0391 (8)	0.0486 (8)	0.0500 (9)	−0.0030 (6)	0.0141 (7)	−0.0003 (7)
C5	0.0369 (8)	0.0504 (8)	0.0408 (8)	0.0042 (6)	0.0135 (7)	0.0057 (7)
C6	0.0491 (9)	0.0479 (9)	0.0378 (8)	0.0066 (7)	0.0118 (7)	0.0070 (7)
C7	0.0465 (9)	0.0443 (8)	0.0388 (8)	0.0021 (6)	0.0090 (7)	0.0038 (6)
C8	0.0545 (10)	0.0541 (9)	0.0385 (9)	−0.0053 (7)	0.0121 (7)	−0.0006 (7)
C9	0.0908 (15)	0.0483 (10)	0.0834 (14)	−0.0055 (9)	0.0396 (12)	0.0099 (9)
C10	0.1054 (18)	0.0477 (11)	0.123 (2)	0.0209 (11)	0.0568 (16)	0.0256 (11)
C11	0.0696 (12)	0.0581 (11)	0.0941 (15)	0.0189 (9)	0.0382 (11)	0.0208 (10)
C12	0.0677 (12)	0.0969 (15)	0.0493 (11)	−0.0041 (11)	−0.0012 (10)	0.0147 (10)
C13	0.0672 (12)	0.0599 (11)	0.0748 (13)	−0.0141 (9)	0.0218 (10)	0.0068 (9)
C14	0.0486 (9)	0.0487 (8)	0.0406 (9)	0.0013 (7)	0.0145 (7)	0.0051 (7)
C15	0.0605 (11)	0.1109 (16)	0.0525 (11)	0.0134 (11)	0.0252 (10)	0.0182 (10)
C16	0.0858 (16)	0.148 (2)	0.0511 (12)	0.0181 (15)	0.0330 (12)	0.0295 (13)
C17	0.0761 (14)	0.0975 (15)	0.0408 (10)	0.0060 (11)	0.0085 (10)	0.0208 (10)
C18	0.0518 (10)	0.0504 (9)	0.0447 (10)	0.0002 (7)	0.0052 (8)	0.0068 (7)
C19	0.0481 (9)	0.0474 (8)	0.0384 (9)	−0.0018 (7)	0.0119 (7)	0.0058 (7)
C20	0.0824 (15)	0.0931 (16)	0.1168 (19)	−0.0398 (13)	0.0406 (15)	−0.0121 (14)
C21	0.0678 (13)	0.0993 (16)	0.0654 (14)	0.0113 (11)	−0.0141 (11)	0.0136 (11)
N1	0.0438 (7)	0.0441 (7)	0.0345 (7)	−0.0023 (5)	0.0066 (6)	0.0032 (6)
O1	0.0527 (7)	0.0679 (8)	0.0662 (8)	−0.0140 (5)	0.0191 (6)	0.0032 (6)
O2A	0.051 (2)	0.120 (2)	0.0707 (14)	−0.040 (2)	−0.0090 (14)	0.0095 (14)
O2B	0.051 (2)	0.120 (2)	0.0707 (14)	−0.040 (2)	−0.0090 (14)	0.0095 (14)
O3	0.0498 (7)	0.0787 (9)	0.0574 (8)	0.0069 (6)	−0.0005 (6)	0.0176 (6)

C1—N1	1.4654 (19)	C12—H12A	0.9600
C1—C6	1.506 (2)	C12—H12B	0.9600
C1—C2	1.537 (2)	C12—H12C	0.9600
C1—H1	0.9800	C13—H13A	0.9600
C2—C3	1.508 (2)	C13—H13B	0.9600
C2—C12	1.526 (2)	C13—H13C	0.9600
C2—H2	0.9800	C14—C19	1.380 (2)
C3—O2B	1.169 (13)	C14—C15	1.383 (2)
C3—O2A	1.240 (4)	C15—C16	1.378 (3)
C3—C4	1.513 (2)	C15—H15	0.9300
C4—C13	1.517 (2)	C16—C17	1.366 (3)
C4—C5	1.539 (2)	C16—H16	0.9300
C4—H4	0.9800	C17—C18	1.377 (2)
C5—N1	1.4570 (18)	C17—H17	0.9300
C5—C14	1.511 (2)	C18—O3	1.3671 (19)
C5—H5	0.9800	C18—C19	1.388 (2)
C6—C7	1.385 (2)	C19—H19	0.9300
C6—C11	1.388 (2)	C20—O1	1.426 (2)
C7—C8	1.387 (2)	C20—H20A	0.9600
C7—H7	0.9300	C20—H20B	0.9600
C8—O1	1.3730 (19)	C20—H20C	0.9600
C8—C9	1.378 (2)	C21—O3	1.430 (2)
C9—C10	1.372 (3)	C21—H21A	0.9600
C9—H9	0.9300	C21—H21B	0.9600
C10—C11	1.374 (3)	C21—H21C	0.9600
C10—H10	0.9300	N1—H1A	0.881 (18)
C11—H11	0.9300
N1—C1—C6	109.30 (12)	C2—C12—H12A	109.5
N1—C1—C2	109.18 (12)	C2—C12—H12B	109.5
C6—C1—C2	112.85 (12)	H12A—C12—H12B	109.5
N1—C1—H1	108.5	C2—C12—H12C	109.5
C6—C1—H1	108.5	H12A—C12—H12C	109.5
C2—C1—H1	108.5	H12B—C12—H12C	109.5
C3—C2—C12	111.93 (14)	C4—C13—H13A	109.5
C3—C2—C1	109.26 (12)	C4—C13—H13B	109.5
C12—C2—C1	112.75 (14)	H13A—C13—H13B	109.5
C3—C2—H2	107.6	C4—C13—H13C	109.5
C12—C2—H2	107.6	H13A—C13—H13C	109.5
C1—C2—H2	107.6	H13B—C13—H13C	109.5
O2B—C3—O2A	30.7 (7)	C19—C14—C15	118.53 (15)
O2B—C3—C2	119.8 (7)	C19—C14—C5	120.44 (13)
O2A—C3—C2	121.1 (2)	C15—C14—C5	121.03 (14)
O2B—C3—C4	117.2 (7)	C16—C15—C14	120.02 (17)
O2A—C3—C4	121.1 (2)	C16—C15—H15	120.0
C2—C3—C4	117.27 (13)	C14—C15—H15	120.0
C3—C4—C13	111.25 (13)	C17—C16—C15	121.45 (17)
C3—C4—C5	108.85 (13)	C17—C16—H16	119.3
C13—C4—C5	112.82 (13)	C15—C16—H16	119.3
C3—C4—H4	107.9	C16—C17—C18	119.18 (17)
C13—C4—H4	107.9	C16—C17—H17	120.4
C5—C4—H4	107.9	C18—C17—H17	120.4
N1—C5—C14	110.05 (12)	O3—C18—C17	124.51 (15)
N1—C5—C4	108.76 (11)	O3—C18—C19	115.71 (14)
C14—C5—C4	111.95 (12)	C17—C18—C19	119.78 (16)
N1—C5—H5	108.7	C14—C19—C18	121.04 (14)
C14—C5—H5	108.7	C14—C19—H19	119.5
C4—C5—H5	108.7	C18—C19—H19	119.5
C7—C6—C11	118.74 (15)	O1—C20—H20A	109.5
C7—C6—C1	120.24 (13)	O1—C20—H20B	109.5
C11—C6—C1	121.02 (14)	H20A—C20—H20B	109.5
C6—C7—C8	120.69 (14)	O1—C20—H20C	109.5
C6—C7—H7	119.7	H20A—C20—H20C	109.5
C8—C7—H7	119.7	H20B—C20—H20C	109.5
O1—C8—C9	124.48 (15)	O3—C21—H21A	109.5
O1—C8—C7	115.50 (14)	O3—C21—H21B	109.5
C9—C8—C7	120.02 (16)	H21A—C21—H21B	109.5
C10—C9—C8	119.12 (16)	O3—C21—H21C	109.5
C10—C9—H9	120.4	H21A—C21—H21C	109.5
C8—C9—H9	120.4	H21B—C21—H21C	109.5
C9—C10—C11	121.50 (17)	C5—N1—C1	113.77 (12)
C9—C10—H10	119.3	C5—N1—H1A	110.5 (11)
C11—C10—H10	119.3	C1—N1—H1A	108.3 (11)
C10—C11—C6	119.93 (17)	C8—O1—C20	117.83 (15)
C10—C11—H11	120.0	C18—O3—C21	118.55 (15)
C6—C11—H11	120.0
N1—C1—C2—C3	51.68 (16)	O1—C8—C9—C10	179.28 (18)
C6—C1—C2—C3	173.44 (13)	C7—C8—C9—C10	−0.1 (3)
N1—C1—C2—C12	176.82 (13)	C8—C9—C10—C11	0.9 (4)
C6—C1—C2—C12	−61.42 (17)	C9—C10—C11—C6	−0.5 (4)
C12—C2—C3—O2B	32.9 (11)	C7—C6—C11—C10	−0.6 (3)
C1—C2—C3—O2B	158.5 (11)	C1—C6—C11—C10	178.52 (18)
C12—C2—C3—O2A	−2.9 (5)	N1—C5—C14—C19	−46.64 (19)
C1—C2—C3—O2A	122.7 (5)	C4—C5—C14—C19	74.44 (17)
C12—C2—C3—C4	−174.39 (15)	N1—C5—C14—C15	133.92 (17)
C1—C2—C3—C4	−48.78 (18)	C4—C5—C14—C15	−105.00 (18)
O2B—C3—C4—C13	−32.1 (10)	C19—C14—C15—C16	−1.0 (3)
O2A—C3—C4—C13	3.0 (5)	C5—C14—C15—C16	178.4 (2)
C2—C3—C4—C13	174.50 (15)	C14—C15—C16—C17	1.2 (4)
O2B—C3—C4—C5	−157.0 (10)	C15—C16—C17—C18	−0.6 (4)
O2A—C3—C4—C5	−121.9 (5)	C16—C17—C18—O3	179.6 (2)
C2—C3—C4—C5	49.58 (18)	C16—C17—C18—C19	−0.3 (3)
C3—C4—C5—N1	−53.41 (15)	C15—C14—C19—C18	0.2 (2)
C13—C4—C5—N1	−177.41 (13)	C5—C14—C19—C18	−179.21 (14)
C3—C4—C5—C14	−175.24 (12)	O3—C18—C19—C14	−179.43 (14)
C13—C4—C5—C14	60.77 (17)	C17—C18—C19—C14	0.4 (3)
N1—C1—C6—C7	50.27 (18)	C14—C5—N1—C1	−172.98 (12)
C2—C1—C6—C7	−71.42 (18)	C4—C5—N1—C1	64.05 (16)
N1—C1—C6—C11	−128.84 (17)	C6—C1—N1—C5	172.93 (12)
C2—C1—C6—C11	109.47 (18)	C2—C1—N1—C5	−63.19 (15)
C11—C6—C7—C8	1.3 (2)	C9—C8—O1—C20	9.7 (3)
C1—C6—C7—C8	−177.79 (14)	C7—C8—O1—C20	−170.90 (17)
C6—C7—C8—O1	179.56 (13)	C17—C18—O3—C21	−1.7 (3)
C6—C7—C8—C9	−1.0 (2)	C19—C18—O3—C21	178.11 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.881 (18)	2.414 (19)	3.2784 (18)	167.1 (15)
C2—H2···O3i	0.98	2.47	3.335 (2)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.881 (18)	2.414 (19)	3.2784 (18)	167.1 (15)
C2—H2⋯O3i	0.98	2.47	3.335 (2)	146

Symmetry code: (i) .