3,3,5,5-Tetra-methyl-r-2,c-6-diphenyl-piperidin-4-one.

The piperidone ring of the title compound, C(21)H(25)NO, adopts a chair conformation with the two phenyl groups equatorially oriented and cis to each other. In the crystal, mol-ecules are linked by weak N-H⋯O hydrogen bonds, forming chains parallel to [100].

Related literature

For some bioactive properties of piperidones, see: Mobio et al. (1989 ▶). For piperidone ring conformations in related compounds, see: Parthiban et al. (2008 ▶); Lakshminarayana et al. (2009 ▶); Ravichandran et al. (2010 ▶). For the synthesis, see: Noller & Baliah (1948 ▶). For ring puckering parameters, see: Nardelli (1983 ▶); Cremer & Pople (1975 ▶).

Experimental

Crystal data

C21H25NO

M = 307.42

Triclinic,

a = 6.9227 (11) Å

b = 11.540 (2) Å

c = 12.472 (2) Å

α = 64.771 (4)°

β = 80.755 (5)°

γ = 72.675 (4)°

V = 859.8 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 295 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.919, T max = 0.986

12752 measured reflections

2659 independent reflections

2123 reflections with I > 2σ(I)

R int = 0.032

θmax = 24.0°

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.152

S = 1.15

2659 reflections

217 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812018983/lr2058sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018983/lr2058Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812018983/lr2058Isup3.cml

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

C21H25NO	Z = 2
Mr = 307.42	F(000) = 332
Triclinic, P1	Dx = 1.187 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9227 (11) Å	Cell parameters from 4779 reflections
b = 11.540 (2) Å	θ = 2.1–23.8°
c = 12.472 (2) Å	µ = 0.07 mm−1
α = 64.771 (4)°	T = 295 K
β = 80.755 (5)°	Block, colourless
γ = 72.675 (4)°	0.30 × 0.25 × 0.20 mm
V = 859.8 (3) Å3

Bruker Kappa APEXII CCD diffractometer	2659 independent reflections
Radiation source: fine-focus sealed tube	2123 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
ω and φ scan	θmax = 24.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −7→7
Tmin = 0.919, Tmax = 0.986	k = −13→13
12752 measured reflections	l = −14→14

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)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.152	w = 1/[σ2(Fo2) + (0.0562P)2 + 0.4957P] where P = (Fo2 + 2Fc2)/3
S = 1.15	(Δ/σ)max < 0.001
2659 reflections	Δρmax = 0.23 e Å−3
217 parameters	Δρmin = −0.18 e Å−3
0 restraints	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 (4)

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
C1	0.7201 (4)	0.4000 (2)	0.1945 (2)	0.0372 (6)
H1	0.7165	0.4280	0.1087	0.045*
C2	0.9321 (4)	0.3963 (2)	0.2220 (2)	0.0407 (6)
C3	1.0898 (4)	0.2903 (2)	0.1901 (2)	0.0435 (6)
C4	1.0442 (4)	0.1603 (2)	0.2102 (2)	0.0446 (6)
C5	0.8169 (4)	0.1810 (2)	0.1951 (2)	0.0386 (6)
H5	0.7920	0.2263	0.1100	0.046*
C6	0.5498 (4)	0.4960 (2)	0.2302 (2)	0.0394 (6)
C7	0.4653 (4)	0.4602 (3)	0.3438 (2)	0.0496 (7)
H7	0.5133	0.3750	0.4003	0.059*
C8	0.3102 (5)	0.5492 (3)	0.3749 (3)	0.0633 (8)
H8	0.2544	0.5234	0.4518	0.076*
C9	0.2383 (5)	0.6751 (3)	0.2932 (3)	0.0657 (9)
H9	0.1351	0.7354	0.3144	0.079*
C10	0.3196 (5)	0.7116 (3)	0.1799 (3)	0.0641 (9)
H10	0.2705	0.7970	0.1239	0.077*
C11	0.4734 (4)	0.6232 (2)	0.1478 (3)	0.0514 (7)
H11	0.5265	0.6493	0.0703	0.062*
C12	0.7552 (4)	0.0522 (2)	0.2417 (2)	0.0408 (6)
C13	0.7551 (4)	−0.0084 (3)	0.1664 (3)	0.0533 (7)
H13	0.7920	0.0311	0.0866	0.064*
C14	0.7008 (5)	−0.1267 (3)	0.2086 (3)	0.0647 (9)
H14	0.7004	−0.1655	0.1568	0.078*
C15	0.6482 (5)	−0.1867 (3)	0.3250 (3)	0.0655 (9)
H15	0.6137	−0.2669	0.3532	0.079*
C16	0.6461 (4)	−0.1284 (3)	0.4009 (3)	0.0597 (8)
H16	0.6098	−0.1689	0.4807	0.072*
C17	0.6982 (4)	−0.0093 (2)	0.3588 (2)	0.0483 (7)
H17	0.6945	0.0300	0.4108	0.058*
C18	0.9507 (5)	0.3605 (3)	0.3540 (3)	0.0632 (8)
H18A	0.9024	0.2832	0.4010	0.095*
H18B	0.8713	0.4332	0.3736	0.095*
H18C	1.0900	0.3429	0.3700	0.095*
C19	0.9807 (4)	0.5297 (3)	0.1504 (3)	0.0569 (8)
H19A	1.1159	0.5236	0.1653	0.085*
H19B	0.8867	0.5960	0.1733	0.085*
H19C	0.9702	0.5535	0.0675	0.085*
C20	1.1125 (5)	0.0629 (3)	0.3352 (3)	0.0691 (9)
H20A	1.2464	0.0646	0.3447	0.104*
H20B	1.1131	−0.0249	0.3467	0.104*
H20C	1.0207	0.0879	0.3927	0.104*
C21	1.1721 (5)	0.1079 (3)	0.1211 (3)	0.0707 (10)
H21A	1.1335	0.1695	0.0422	0.106*
H21B	1.1507	0.0238	0.1359	0.106*
H21C	1.3126	0.0973	0.1293	0.106*
N1	0.6901 (3)	0.26610 (18)	0.25244 (18)	0.0388 (5)
O1	1.2574 (3)	0.30563 (19)	0.1531 (2)	0.0641 (6)
H1A	0.554 (4)	0.268 (2)	0.251 (2)	0.042 (7)*

	U11	U22	U33	U12	U13	U23
C1	0.0395 (14)	0.0324 (12)	0.0436 (14)	−0.0100 (10)	−0.0031 (10)	−0.0179 (11)
C2	0.0389 (14)	0.0400 (14)	0.0502 (15)	−0.0132 (11)	−0.0018 (11)	−0.0225 (12)
C3	0.0344 (15)	0.0428 (14)	0.0531 (15)	−0.0111 (11)	−0.0032 (11)	−0.0179 (12)
C4	0.0370 (15)	0.0330 (13)	0.0583 (16)	−0.0050 (10)	0.0008 (11)	−0.0169 (12)
C5	0.0393 (14)	0.0320 (12)	0.0441 (14)	−0.0047 (10)	−0.0036 (10)	−0.0171 (11)
C6	0.0391 (14)	0.0319 (13)	0.0546 (16)	−0.0104 (10)	−0.0028 (11)	−0.0230 (12)
C7	0.0482 (16)	0.0434 (15)	0.0598 (17)	−0.0111 (12)	0.0030 (13)	−0.0254 (13)
C8	0.0566 (19)	0.073 (2)	0.078 (2)	−0.0182 (16)	0.0122 (15)	−0.0510 (18)
C9	0.0520 (19)	0.0570 (19)	0.105 (3)	−0.0006 (14)	−0.0078 (17)	−0.055 (2)
C10	0.063 (2)	0.0361 (15)	0.094 (2)	0.0003 (13)	−0.0180 (18)	−0.0303 (16)
C11	0.0548 (17)	0.0365 (14)	0.0644 (18)	−0.0099 (12)	−0.0086 (13)	−0.0207 (13)
C12	0.0366 (14)	0.0295 (12)	0.0541 (16)	−0.0022 (10)	−0.0059 (11)	−0.0176 (11)
C13	0.0601 (19)	0.0417 (15)	0.0627 (18)	−0.0091 (13)	−0.0059 (14)	−0.0266 (14)
C14	0.070 (2)	0.0442 (17)	0.093 (2)	−0.0083 (14)	−0.0144 (18)	−0.0399 (17)
C15	0.0576 (19)	0.0381 (16)	0.102 (3)	−0.0130 (13)	−0.0099 (17)	−0.0264 (17)
C16	0.0537 (19)	0.0442 (16)	0.073 (2)	−0.0170 (13)	−0.0043 (14)	−0.0122 (15)
C17	0.0473 (16)	0.0415 (14)	0.0591 (17)	−0.0146 (12)	−0.0013 (12)	−0.0211 (13)
C18	0.0543 (19)	0.086 (2)	0.0630 (19)	−0.0170 (16)	−0.0097 (14)	−0.0406 (17)
C19	0.0506 (18)	0.0462 (16)	0.085 (2)	−0.0197 (13)	0.0024 (14)	−0.0335 (15)
C20	0.0489 (18)	0.0526 (18)	0.084 (2)	−0.0073 (14)	−0.0257 (16)	−0.0032 (16)
C21	0.0541 (19)	0.0559 (18)	0.108 (3)	−0.0136 (14)	0.0245 (17)	−0.0487 (18)
N1	0.0331 (12)	0.0320 (11)	0.0558 (13)	−0.0103 (8)	0.0015 (9)	−0.0217 (9)
O1	0.0380 (12)	0.0621 (13)	0.0986 (16)	−0.0187 (9)	0.0098 (10)	−0.0387 (12)

C1—N1	1.464 (3)	C11—H11	0.9300
C1—C6	1.513 (3)	C12—C17	1.375 (4)
C1—C2	1.545 (3)	C12—C13	1.390 (4)
C1—H1	0.9800	C13—C14	1.383 (4)
C2—C19	1.523 (3)	C13—H13	0.9300
C2—C3	1.525 (3)	C14—C15	1.359 (5)
C2—C18	1.534 (4)	C14—H14	0.9300
C3—O1	1.213 (3)	C15—C16	1.372 (4)
C3—C4	1.532 (3)	C15—H15	0.9300
C4—C21	1.523 (4)	C16—C17	1.383 (4)
C4—C20	1.531 (4)	C16—H16	0.9300
C4—C5	1.550 (3)	C17—H17	0.9300
C5—N1	1.460 (3)	C18—H18A	0.9600
C5—C12	1.514 (3)	C18—H18B	0.9600
C5—H5	0.9800	C18—H18C	0.9600
C6—C7	1.378 (4)	C19—H19A	0.9600
C6—C11	1.385 (3)	C19—H19B	0.9600
C7—C8	1.381 (4)	C19—H19C	0.9600
C7—H7	0.9300	C20—H20A	0.9600
C8—C9	1.367 (4)	C20—H20B	0.9600
C8—H8	0.9300	C20—H20C	0.9600
C9—C10	1.367 (5)	C21—H21A	0.9600
C9—H9	0.9300	C21—H21B	0.9600
C10—C11	1.378 (4)	C21—H21C	0.9600
C10—H10	0.9300	N1—H1A	0.94 (3)
N1—C1—C6	110.46 (19)	C17—C12—C13	117.6 (2)
N1—C1—C2	109.22 (19)	C17—C12—C5	121.9 (2)
C6—C1—C2	113.51 (18)	C13—C12—C5	120.5 (2)
N1—C1—H1	107.8	C14—C13—C12	120.9 (3)
C6—C1—H1	107.8	C14—C13—H13	119.6
C2—C1—H1	107.8	C12—C13—H13	119.6
C19—C2—C3	109.0 (2)	C15—C14—C13	120.5 (3)
C19—C2—C18	108.4 (2)	C15—C14—H14	119.8
C3—C2—C18	107.4 (2)	C13—C14—H14	119.8
C19—C2—C1	110.9 (2)	C14—C15—C16	119.7 (3)
C3—C2—C1	108.89 (19)	C14—C15—H15	120.2
C18—C2—C1	112.2 (2)	C16—C15—H15	120.2
O1—C3—C2	119.9 (2)	C15—C16—C17	120.0 (3)
O1—C3—C4	118.9 (2)	C15—C16—H16	120.0
C2—C3—C4	121.1 (2)	C17—C16—H16	120.0
C21—C4—C20	108.7 (2)	C12—C17—C16	121.4 (3)
C21—C4—C3	108.7 (2)	C12—C17—H17	119.3
C20—C4—C3	106.0 (2)	C16—C17—H17	119.3
C21—C4—C5	109.6 (2)	C2—C18—H18A	109.5
C20—C4—C5	112.4 (2)	C2—C18—H18B	109.5
C3—C4—C5	111.33 (19)	H18A—C18—H18B	109.5
N1—C5—C12	109.7 (2)	C2—C18—H18C	109.5
N1—C5—C4	110.6 (2)	H18A—C18—H18C	109.5
C12—C5—C4	113.06 (19)	H18B—C18—H18C	109.5
N1—C5—H5	107.7	C2—C19—H19A	109.5
C12—C5—H5	107.7	C2—C19—H19B	109.5
C4—C5—H5	107.7	H19A—C19—H19B	109.5
C7—C6—C11	118.1 (2)	C2—C19—H19C	109.5
C7—C6—C1	121.7 (2)	H19A—C19—H19C	109.5
C11—C6—C1	120.2 (2)	H19B—C19—H19C	109.5
C6—C7—C8	120.9 (3)	C4—C20—H20A	109.5
C6—C7—H7	119.5	C4—C20—H20B	109.5
C8—C7—H7	119.5	H20A—C20—H20B	109.5
C9—C8—C7	120.3 (3)	C4—C20—H20C	109.5
C9—C8—H8	119.8	H20A—C20—H20C	109.5
C7—C8—H8	119.8	H20B—C20—H20C	109.5
C8—C9—C10	119.4 (3)	C4—C21—H21A	109.5
C8—C9—H9	120.3	C4—C21—H21B	109.5
C10—C9—H9	120.3	H21A—C21—H21B	109.5
C9—C10—C11	120.7 (3)	C4—C21—H21C	109.5
C9—C10—H10	119.6	H21A—C21—H21C	109.5
C11—C10—H10	119.6	H21B—C21—H21C	109.5
C10—C11—C6	120.5 (3)	C5—N1—C1	111.10 (19)
C10—C11—H11	119.7	C5—N1—H1A	109.0 (15)
C6—C11—H11	119.7	C1—N1—H1A	111.2 (15)
N1—C1—C2—C19	172.5 (2)	N1—C1—C6—C11	−141.9 (2)
C6—C1—C2—C19	−63.7 (3)	C2—C1—C6—C11	95.1 (3)
N1—C1—C2—C3	52.6 (3)	C11—C6—C7—C8	−0.6 (4)
C6—C1—C2—C3	176.3 (2)	C1—C6—C7—C8	179.8 (2)
N1—C1—C2—C18	−66.1 (3)	C6—C7—C8—C9	−0.3 (4)
C6—C1—C2—C18	57.6 (3)	C7—C8—C9—C10	0.8 (5)
C19—C2—C3—O1	25.8 (3)	C8—C9—C10—C11	−0.4 (5)
C18—C2—C3—O1	−91.4 (3)	C9—C10—C11—C6	−0.5 (4)
C1—C2—C3—O1	146.9 (2)	C7—C6—C11—C10	1.0 (4)
C19—C2—C3—C4	−157.6 (2)	C1—C6—C11—C10	−179.4 (2)
C18—C2—C3—C4	85.2 (3)	N1—C5—C12—C17	−37.9 (3)
C1—C2—C3—C4	−36.5 (3)	C4—C5—C12—C17	86.1 (3)
O1—C3—C4—C21	−30.6 (3)	N1—C5—C12—C13	142.3 (2)
C2—C3—C4—C21	152.7 (2)	C4—C5—C12—C13	−93.7 (3)
O1—C3—C4—C20	86.0 (3)	C17—C12—C13—C14	−0.4 (4)
C2—C3—C4—C20	−90.6 (3)	C5—C12—C13—C14	179.4 (2)
O1—C3—C4—C5	−151.4 (2)	C12—C13—C14—C15	−0.6 (4)
C2—C3—C4—C5	31.9 (3)	C13—C14—C15—C16	0.9 (5)
C21—C4—C5—N1	−163.2 (2)	C14—C15—C16—C17	−0.2 (4)
C20—C4—C5—N1	75.8 (3)	C13—C12—C17—C16	1.2 (4)
C3—C4—C5—N1	−42.9 (3)	C5—C12—C17—C16	−178.6 (2)
C21—C4—C5—C12	73.3 (3)	C15—C16—C17—C12	−0.9 (4)
C20—C4—C5—C12	−47.7 (3)	C12—C5—N1—C1	−169.68 (19)
C3—C4—C5—C12	−166.4 (2)	C4—C5—N1—C1	64.9 (2)
N1—C1—C6—C7	37.7 (3)	C6—C1—N1—C5	163.89 (19)
C2—C1—C6—C7	−85.3 (3)	C2—C1—N1—C5	−70.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.94 (3)	2.39 (3)	3.258 (3)	153 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.94 (3)	2.39 (3)	3.258 (3)	153 (2)

Symmetry code: (i) .