1-Formyl-c-3,t-3-dimethyl-r-2,c-6-di-phenyl-piperidin-4-one.

In the title compound, C(20)H(21)NO(2), the piperidine ring adopts a distorted boat conformation. The phenyl rings substituted at the 2- and 6-positions of the piperidine ring subtend angles of 86.0 (1) and 67.3 (1)° with the mean plane of the piperidine ring (all six non-H atoms). The crystal packing features C-H⋯O inter-actions.

Related literature

For the biological activity of piperidine derivatives, see: Aridoss et al. (2009 ▶); Nalanishi et al. (1974 ▶); Michael (2001 ▶); Pinder (1992 ▶); Rubiralta et al. (1991 ▶). 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

C20H21NO2

M = 307.38

Monoclinic,

a = 10.6604 (6) Å

b = 15.7278 (7) Å

c = 10.8066 (5) Å

β = 110.120 (2)°

V = 1701.31 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX CCD detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.985, T max = 0.985

16240 measured reflections

4162 independent reflections

2769 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.125

S = 1.04

4162 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.13 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶); data reduction: SAINT-Plus; 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/S1600536812007015/bt5783sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007015/bt5783Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812007015/bt5783Isup3.cml

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

C20H21NO2	F(000) = 656
Mr = 307.38	Dx = 1.200 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2769 reflections
a = 10.6604 (6) Å	θ = 2.3–28.3°
b = 15.7278 (7) Å	µ = 0.08 mm−1
c = 10.8066 (5) Å	T = 293 K
β = 110.120 (2)°	Block, yellow
V = 1701.31 (15) Å3	0.20 × 0.20 × 0.20 mm
Z = 4

Bruker SMART APEX CCD detector diffractometer	4162 independent reflections
Radiation source: fine-focus sealed tube	2769 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
ω scans	θmax = 28.3°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −13→9
Tmin = 0.985, Tmax = 0.985	k = −17→20
16240 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)] = 0.042	H-atom parameters constrained
wR(F2) = 0.125	w = 1/[σ2(Fo2) + (0.0489P)2 + 0.2736P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
4162 reflections	Δρmax = 0.19 e Å−3
209 parameters	Δρmin = −0.13 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: 0.0063 (15)

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
O1	0.33930 (11)	0.19983 (7)	0.96574 (9)	0.0689 (3)
O2	0.12616 (13)	0.21093 (8)	0.35746 (10)	0.0845 (4)
N1	0.20536 (10)	0.17426 (7)	0.75311 (10)	0.0487 (3)
C2	0.31776 (13)	0.17185 (9)	0.70280 (12)	0.0483 (3)
H2	0.3914	0.2017	0.7688	0.058*
C3	0.28375 (14)	0.22558 (9)	0.57618 (13)	0.0554 (4)
C4	0.15392 (15)	0.19561 (10)	0.47344 (13)	0.0597 (4)
C5	0.05906 (14)	0.14749 (10)	0.52365 (12)	0.0598 (4)
H5A	0.0781	0.0872	0.5226	0.072*
H5B	−0.0312	0.1567	0.4633	0.072*
C6	0.06466 (13)	0.17169 (9)	0.66235 (13)	0.0530 (3)
H6	0.0275	0.2290	0.6582	0.064*
C7	0.22970 (15)	0.19192 (9)	0.88088 (13)	0.0563 (4)
H7	0.1558	0.1988	0.9071	0.068*
C8	0.36733 (12)	0.08118 (9)	0.69907 (12)	0.0477 (3)
C9	0.45199 (14)	0.04765 (10)	0.81673 (13)	0.0583 (4)
H9	0.4758	0.0808	0.8926	0.070*
C10	0.50188 (17)	−0.03415 (12)	0.82365 (16)	0.0715 (5)
H10	0.5580	−0.0555	0.9038	0.086*
C11	0.46891 (17)	−0.08374 (11)	0.71304 (19)	0.0732 (5)
H11	0.5018	−0.1389	0.7177	0.088*
C12	0.38724 (18)	−0.05151 (12)	0.59586 (18)	0.0781 (5)
H12	0.3655	−0.0847	0.5201	0.094*
C13	0.33629 (16)	0.03008 (11)	0.58839 (15)	0.0683 (4)
H13	0.2803	0.0508	0.5077	0.082*
C14	0.40046 (17)	0.22591 (12)	0.52432 (16)	0.0751 (5)
H14A	0.4797	0.2455	0.5923	0.113*
H14B	0.3801	0.2631	0.4495	0.113*
H14C	0.4148	0.1693	0.4986	0.113*
C15	0.25767 (18)	0.31820 (10)	0.60864 (17)	0.0709 (4)
H15A	0.1843	0.3194	0.6409	0.106*
H15B	0.2363	0.3523	0.5304	0.106*
H15C	0.3362	0.3404	0.6747	0.106*
C16	−0.01874 (13)	0.11249 (10)	0.71207 (13)	0.0553 (4)
C17	−0.14145 (15)	0.13908 (12)	0.71422 (15)	0.0681 (4)
H17	−0.1720	0.1935	0.6854	0.082*
C18	−0.21912 (18)	0.08524 (16)	0.75901 (18)	0.0855 (6)
H18	−0.3018	0.1035	0.7599	0.103*
C19	−0.1747 (2)	0.00528 (16)	0.8021 (2)	0.0905 (6)
H19	−0.2269	−0.0307	0.8326	0.109*
C20	−0.0538 (2)	−0.02166 (14)	0.8001 (2)	0.0942 (6)
H20	−0.0238	−0.0761	0.8291	0.113*
C21	0.02406 (18)	0.03149 (12)	0.75529 (19)	0.0774 (5)
H21	0.1063	0.0126	0.7542	0.093*

	U11	U22	U33	U12	U13	U23
O1	0.0658 (7)	0.0879 (8)	0.0450 (5)	−0.0068 (6)	0.0089 (5)	−0.0128 (5)
O2	0.0962 (9)	0.1036 (10)	0.0445 (6)	0.0147 (7)	0.0125 (5)	0.0114 (5)
N1	0.0453 (6)	0.0573 (7)	0.0408 (5)	0.0030 (5)	0.0113 (4)	−0.0060 (5)
C2	0.0450 (7)	0.0562 (8)	0.0407 (6)	0.0011 (6)	0.0112 (5)	−0.0026 (5)
C3	0.0598 (8)	0.0586 (9)	0.0485 (7)	0.0094 (7)	0.0194 (6)	0.0058 (6)
C4	0.0674 (9)	0.0618 (9)	0.0452 (7)	0.0186 (7)	0.0135 (6)	0.0028 (6)
C5	0.0524 (8)	0.0704 (10)	0.0453 (7)	0.0085 (7)	0.0024 (6)	−0.0057 (6)
C6	0.0457 (7)	0.0581 (9)	0.0497 (7)	0.0070 (6)	0.0095 (5)	−0.0057 (6)
C7	0.0590 (8)	0.0627 (9)	0.0473 (7)	−0.0003 (7)	0.0182 (6)	−0.0084 (6)
C8	0.0401 (6)	0.0572 (8)	0.0456 (6)	0.0030 (6)	0.0144 (5)	0.0026 (5)
C9	0.0570 (8)	0.0741 (10)	0.0458 (7)	0.0094 (7)	0.0201 (6)	0.0095 (6)
C10	0.0744 (10)	0.0827 (12)	0.0666 (9)	0.0262 (9)	0.0358 (8)	0.0315 (8)
C11	0.0781 (11)	0.0592 (10)	0.0960 (12)	0.0132 (8)	0.0477 (10)	0.0143 (9)
C12	0.0754 (11)	0.0703 (12)	0.0831 (11)	0.0124 (9)	0.0204 (9)	−0.0172 (9)
C13	0.0650 (9)	0.0731 (11)	0.0552 (8)	0.0185 (8)	0.0057 (7)	−0.0085 (7)
C14	0.0763 (11)	0.0899 (13)	0.0677 (9)	0.0150 (9)	0.0357 (8)	0.0199 (8)
C15	0.0842 (11)	0.0568 (10)	0.0740 (10)	0.0053 (8)	0.0302 (9)	0.0061 (7)
C16	0.0469 (7)	0.0628 (9)	0.0522 (7)	−0.0006 (7)	0.0117 (6)	−0.0136 (6)
C17	0.0517 (8)	0.0876 (12)	0.0619 (9)	0.0046 (8)	0.0157 (7)	−0.0091 (8)
C18	0.0546 (10)	0.1252 (18)	0.0783 (11)	−0.0028 (11)	0.0249 (8)	−0.0087 (11)
C19	0.0761 (13)	0.1046 (17)	0.0937 (13)	−0.0247 (12)	0.0330 (10)	−0.0060 (12)
C20	0.0880 (14)	0.0718 (13)	0.1283 (17)	−0.0076 (10)	0.0441 (13)	0.0039 (11)
C21	0.0652 (10)	0.0650 (11)	0.1073 (13)	0.0013 (8)	0.0365 (10)	−0.0046 (9)

O1—C7	1.2183 (17)	C10—H10	0.9300
O2—C4	1.2088 (16)	C11—C12	1.364 (2)
N1—C7	1.3433 (16)	C11—H11	0.9300
N1—C2	1.4768 (16)	C12—C13	1.385 (2)
N1—C6	1.4837 (16)	C12—H12	0.9300
C2—C8	1.5261 (19)	C13—H13	0.9300
C2—C3	1.5416 (18)	C14—H14A	0.9600
C2—H2	0.9800	C14—H14B	0.9600
C3—C4	1.521 (2)	C14—H14C	0.9600
C3—C14	1.530 (2)	C15—H15A	0.9600
C3—C15	1.546 (2)	C15—H15B	0.9600
C4—C5	1.506 (2)	C15—H15C	0.9600
C5—C6	1.5276 (18)	C16—C21	1.379 (2)
C5—H5A	0.9700	C16—C17	1.381 (2)
C5—H5B	0.9700	C17—C18	1.383 (3)
C6—C16	1.508 (2)	C17—H17	0.9300
C6—H6	0.9800	C18—C19	1.368 (3)
C7—H7	0.9300	C18—H18	0.9300
C8—C13	1.3834 (19)	C19—C20	1.364 (3)
C8—C9	1.3856 (18)	C19—H19	0.9300
C9—C10	1.384 (2)	C20—C21	1.378 (3)
C9—H9	0.9300	C20—H20	0.9300
C10—C11	1.368 (2)	C21—H21	0.9300
C7—N1—C2	119.30 (11)	C9—C10—H10	119.9
C7—N1—C6	118.63 (11)	C12—C11—C10	119.29 (16)
C2—N1—C6	121.31 (10)	C12—C11—H11	120.4
N1—C2—C8	111.46 (11)	C10—C11—H11	120.4
N1—C2—C3	109.86 (10)	C11—C12—C13	120.72 (16)
C8—C2—C3	117.81 (11)	C11—C12—H12	119.6
N1—C2—H2	105.6	C13—C12—H12	119.6
C8—C2—H2	105.6	C8—C13—C12	121.03 (14)
C3—C2—H2	105.6	C8—C13—H13	119.5
C4—C3—C14	112.59 (12)	C12—C13—H13	119.5
C4—C3—C2	110.81 (12)	C3—C14—H14A	109.5
C14—C3—C2	110.75 (11)	C3—C14—H14B	109.5
C4—C3—C15	105.55 (12)	H14A—C14—H14B	109.5
C14—C3—C15	108.19 (13)	C3—C14—H14C	109.5
C2—C3—C15	108.72 (11)	H14A—C14—H14C	109.5
O2—C4—C5	121.24 (14)	H14B—C14—H14C	109.5
O2—C4—C3	122.13 (15)	C3—C15—H15A	109.5
C5—C4—C3	116.61 (11)	C3—C15—H15B	109.5
C4—C5—C6	115.08 (12)	H15A—C15—H15B	109.5
C4—C5—H5A	108.5	C3—C15—H15C	109.5
C6—C5—H5A	108.5	H15A—C15—H15C	109.5
C4—C5—H5B	108.5	H15B—C15—H15C	109.5
C6—C5—H5B	108.5	C21—C16—C17	118.60 (16)
H5A—C5—H5B	107.5	C21—C16—C6	121.60 (13)
N1—C6—C16	111.54 (11)	C17—C16—C6	119.79 (14)
N1—C6—C5	110.17 (11)	C16—C17—C18	120.33 (18)
C16—C6—C5	111.52 (12)	C16—C17—H17	119.8
N1—C6—H6	107.8	C18—C17—H17	119.8
C16—C6—H6	107.8	C19—C18—C17	120.22 (18)
C5—C6—H6	107.8	C19—C18—H18	119.9
O1—C7—N1	126.23 (14)	C17—C18—H18	119.9
O1—C7—H7	116.9	C20—C19—C18	119.9 (2)
N1—C7—H7	116.9	C20—C19—H19	120.0
C13—C8—C9	117.32 (13)	C18—C19—H19	120.0
C13—C8—C2	125.71 (12)	C19—C20—C21	120.2 (2)
C9—C8—C2	116.97 (12)	C19—C20—H20	119.9
C10—C9—C8	121.34 (14)	C21—C20—H20	119.9
C10—C9—H9	119.3	C20—C21—C16	120.67 (17)
C8—C9—H9	119.3	C20—C21—H21	119.7
C11—C10—C9	120.28 (14)	C16—C21—H21	119.7
C11—C10—H10	119.9
C7—N1—C2—C8	96.72 (14)	C6—N1—C7—O1	−176.66 (14)
C6—N1—C2—C8	−93.42 (13)	N1—C2—C8—C13	100.41 (16)
C7—N1—C2—C3	−130.81 (13)	C3—C2—C8—C13	−27.9 (2)
C6—N1—C2—C3	39.05 (16)	N1—C2—C8—C9	−80.34 (14)
N1—C2—C3—C4	−55.83 (14)	C3—C2—C8—C9	151.32 (13)
C8—C2—C3—C4	73.26 (15)	C13—C8—C9—C10	−1.0 (2)
N1—C2—C3—C14	178.49 (12)	C2—C8—C9—C10	179.73 (13)
C8—C2—C3—C14	−52.43 (17)	C8—C9—C10—C11	0.5 (2)
N1—C2—C3—C15	59.74 (15)	C9—C10—C11—C12	0.5 (3)
C8—C2—C3—C15	−171.17 (12)	C10—C11—C12—C13	−0.9 (3)
C14—C3—C4—O2	−34.5 (2)	C9—C8—C13—C12	0.5 (2)
C2—C3—C4—O2	−159.11 (14)	C2—C8—C13—C12	179.78 (15)
C15—C3—C4—O2	83.37 (17)	C11—C12—C13—C8	0.4 (3)
C14—C3—C4—C5	147.10 (14)	N1—C6—C16—C21	−47.78 (18)
C2—C3—C4—C5	22.44 (17)	C5—C6—C16—C21	75.87 (17)
C15—C3—C4—C5	−95.08 (15)	N1—C6—C16—C17	132.58 (13)
O2—C4—C5—C6	−148.57 (14)	C5—C6—C16—C17	−103.77 (15)
C3—C4—C5—C6	29.89 (18)	C21—C16—C17—C18	0.0 (2)
C7—N1—C6—C16	−53.53 (16)	C6—C16—C17—C18	179.70 (14)
C2—N1—C6—C16	136.54 (12)	C16—C17—C18—C19	0.3 (3)
C7—N1—C6—C5	−177.94 (13)	C17—C18—C19—C20	−0.4 (3)
C2—N1—C6—C5	12.13 (18)	C18—C19—C20—C21	0.2 (3)
C4—C5—C6—N1	−47.61 (17)	C19—C20—C21—C16	0.1 (3)
C4—C5—C6—C16	−172.03 (12)	C17—C16—C21—C20	−0.2 (3)
C2—N1—C7—O1	−6.5 (2)	C6—C16—C21—C20	−179.87 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1i	0.98	2.59	3.2951 (17)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1i	0.98	2.59	3.2951 (17)	129

Symmetry code: (i) .