1-Formyl-t-3,t-5-dimethyl-r-2,c-6-diphenyl-piperidin-4-one.

In the title compound, C(20)H(21)NO(2), the piperidine ring adopts a distorted boat conformation. The dihedral angle between the two phenyl rings is 61.33 (18)°. In the crystal, inter-molecular C-H⋯O inter-actions link the mol-ecules into zigzag C(5) chains running parallel to [100].

Related literature

For general background to piperidine derivatives, see: Perumal et al. (2001 ▶); Dimmock et al. (2001 ▶). For asymmetry parameters, see: Nardelli (1983 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the synthesis, see: Jeyaraman et al. (1999 ▶).

Experimental

Crystal data

C20H21NO2

M = 307.38

Orthorhombic,

a = 7.4303 (4) Å

b = 15.3567 (6) Å

c = 29.6732 (13) Å

V = 3385.9 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 292 K

0.22 × 0.19 × 0.16 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.983, T max = 0.988

16882 measured reflections

4198 independent reflections

2097 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.194

S = 1.02

4198 reflections

213 parameters

25 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.23 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 datablocks global, I. DOI: 10.1107/S1600536810018490/ci5087sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018490/ci5087Isup2.hkl

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

C20H21NO2	F(000) = 1312
Mr = 307.38	Dx = 1.206 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1246 reflections
a = 7.4303 (4) Å	θ = 1.4–28.4°
b = 15.3567 (6) Å	µ = 0.08 mm−1
c = 29.6732 (13) Å	T = 292 K
V = 3385.9 (3) Å3	Block, colourless
Z = 8	0.22 × 0.19 × 0.16 mm

Bruker SMART APEXII area-detector diffractometer	4198 independent reflections
Radiation source: fine-focus sealed tube	2097 reflections with I > 2σ(I)
graphite	Rint = 0.030
ω and φ scans	θmax = 28.4°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −9→6
Tmin = 0.983, Tmax = 0.988	k = −20→18
16882 measured reflections	l = −39→38

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.194	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0741P)2 + 1.1948P] where P = (Fo2 + 2Fc2)/3
4198 reflections	(Δ/σ)max = 0.001
213 parameters	Δρmax = 0.37 e Å−3
25 restraints	Δρmin = −0.22 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.0192 (4)	0.2060 (2)	0.13459 (14)	0.1697 (16)
O2	0.6395 (3)	0.38855 (13)	0.21978 (6)	0.0841 (6)
N1	0.2046 (3)	0.31856 (13)	0.14813 (8)	0.0690 (6)
C2	0.3721 (3)	0.27494 (15)	0.13546 (9)	0.0645 (7)
H2	0.3426	0.2132	0.1317	0.077*
C3	0.5024 (3)	0.28034 (15)	0.17521 (8)	0.0565 (6)
H3	0.6204	0.2596	0.1651	0.068*
C4	0.5235 (3)	0.37170 (15)	0.19238 (8)	0.0563 (6)
C5	0.3986 (3)	0.44063 (14)	0.17429 (8)	0.0535 (6)
H5	0.4444	0.4570	0.1445	0.064*
C6	0.2059 (3)	0.40703 (16)	0.16730 (8)	0.0586 (6)
H6	0.1498	0.4034	0.1971	0.070*
C7	0.0458 (5)	0.2769 (3)	0.14840 (17)	0.1186 (15)
C8	0.4415 (4)	0.30662 (16)	0.09006 (9)	0.0715 (8)
C9	0.3332 (6)	0.2922 (2)	0.05318 (12)	0.1179 (14)
H9	0.2243	0.2632	0.0569	0.141*
C10	0.3834 (9)	0.3199 (3)	0.01118 (15)	0.1455 (18)
H10	0.3106	0.3078	−0.0135	0.175*
C11	0.5382 (9)	0.3649 (3)	0.00538 (13)	0.1369 (17)
H11	0.5679	0.3869	−0.0229	0.164*
C12	0.6510 (6)	0.3778 (3)	0.04115 (13)	0.1199 (14)
H12	0.7601	0.4065	0.0371	0.144*
C13	0.6019 (5)	0.3479 (2)	0.08344 (10)	0.0854 (9)
H13	0.6794	0.3560	0.1077	0.103*
C14	0.4401 (4)	0.22289 (18)	0.21443 (10)	0.0781 (8)
H14A	0.5236	0.2281	0.2390	0.117*
H14B	0.4348	0.1633	0.2047	0.117*
H14C	0.3229	0.2413	0.2242	0.117*
C15	0.3989 (4)	0.52323 (17)	0.20290 (10)	0.0779 (8)
H15A	0.3343	0.5128	0.2304	0.117*
H15B	0.3418	0.5695	0.1865	0.117*
H15C	0.5207	0.5393	0.2098	0.117*
C16	0.0934 (3)	0.46917 (17)	0.13948 (9)	0.0627 (6)
C17	−0.0611 (4)	0.50498 (19)	0.15754 (11)	0.0781 (8)
H17	−0.0950	0.4895	0.1866	0.094*
C18	−0.1656 (4)	0.5623 (2)	0.13407 (17)	0.1041 (12)
H18	−0.2686	0.5855	0.1472	0.125*
C19	−0.1192 (6)	0.5849 (2)	0.09201 (18)	0.1146 (14)
H19	−0.1902	0.6241	0.0760	0.138*
C20	0.0328 (6)	0.5506 (2)	0.07227 (12)	0.1109 (12)
H20	0.0638	0.5662	0.0430	0.133*
C21	0.1400 (5)	0.4924 (2)	0.09632 (10)	0.0881 (9)
H21	0.2432	0.4694	0.0832	0.106*
H7	−0.076 (5)	0.287 (2)	0.1562 (11)	0.106*

	U11	U22	U33	U12	U13	U23
O1	0.113 (2)	0.099 (2)	0.298 (4)	−0.0455 (18)	−0.089 (2)	0.053 (2)
O2	0.0795 (13)	0.0781 (13)	0.0947 (14)	−0.0123 (10)	−0.0379 (11)	−0.0045 (10)
N1	0.0443 (11)	0.0572 (12)	0.1055 (16)	−0.0146 (10)	−0.0220 (11)	0.0253 (11)
C2	0.0677 (16)	0.0427 (12)	0.0832 (17)	−0.0081 (12)	−0.0297 (13)	0.0010 (12)
C3	0.0484 (12)	0.0515 (13)	0.0695 (14)	−0.0012 (11)	−0.0139 (11)	0.0017 (11)
C4	0.0486 (12)	0.0571 (14)	0.0631 (14)	−0.0099 (11)	−0.0099 (11)	0.0045 (11)
C5	0.0527 (12)	0.0480 (12)	0.0597 (13)	−0.0046 (10)	0.0025 (10)	0.0044 (10)
C6	0.0474 (12)	0.0678 (15)	0.0606 (13)	0.0004 (11)	0.0032 (10)	0.0163 (12)
C7	0.085 (2)	0.078 (2)	0.193 (4)	−0.038 (2)	−0.057 (3)	0.057 (2)
C8	0.096 (2)	0.0484 (13)	0.0705 (17)	0.0024 (14)	−0.0257 (15)	−0.0083 (12)
C9	0.172 (4)	0.095 (2)	0.087 (2)	−0.018 (2)	−0.062 (2)	0.0030 (19)
C10	0.222 (5)	0.127 (4)	0.087 (3)	−0.001 (4)	−0.060 (3)	−0.003 (2)
C11	0.222 (5)	0.120 (3)	0.069 (2)	0.018 (3)	0.006 (3)	−0.008 (2)
C12	0.153 (4)	0.123 (3)	0.083 (2)	−0.004 (3)	0.030 (3)	−0.015 (2)
C13	0.101 (2)	0.089 (2)	0.0661 (17)	−0.0029 (19)	0.0057 (16)	−0.0164 (15)
C14	0.0777 (18)	0.0679 (17)	0.0887 (19)	−0.0093 (14)	−0.0188 (15)	0.0189 (14)
C15	0.094 (2)	0.0595 (16)	0.0801 (18)	0.0007 (15)	0.0063 (16)	−0.0074 (14)
C16	0.0525 (13)	0.0661 (15)	0.0696 (15)	0.0061 (12)	−0.0013 (11)	0.0106 (12)
C17	0.0534 (15)	0.0730 (18)	0.108 (2)	0.0041 (14)	0.0022 (15)	0.0017 (16)
C18	0.0604 (18)	0.070 (2)	0.182 (4)	0.0121 (16)	−0.019 (2)	0.005 (2)
C19	0.095 (3)	0.075 (2)	0.174 (4)	0.011 (2)	−0.054 (3)	0.029 (3)
C20	0.137 (3)	0.098 (3)	0.097 (2)	0.008 (3)	−0.023 (2)	0.037 (2)
C21	0.097 (2)	0.089 (2)	0.0784 (18)	0.0259 (17)	0.0042 (16)	0.0265 (16)

O1—C7	1.180 (5)	C10—H10	0.93
O2—C4	1.213 (3)	C11—C12	1.367 (6)
N1—C7	1.342 (4)	C11—H11	0.93
N1—C2	1.462 (3)	C12—C13	1.385 (4)
N1—C6	1.473 (3)	C12—H12	0.93
C2—C8	1.522 (4)	C13—H13	0.93
C2—C3	1.528 (3)	C14—H14A	0.96
C2—H2	0.98	C14—H14B	0.96
C3—C4	1.501 (3)	C14—H14C	0.96
C3—C14	1.532 (3)	C15—H15A	0.96
C3—H3	0.98	C15—H15B	0.96
C4—C5	1.507 (3)	C15—H15C	0.96
C5—C15	1.526 (3)	C16—C21	1.374 (4)
C5—C6	1.536 (3)	C16—C17	1.381 (4)
C5—H5	0.98	C17—C18	1.365 (4)
C6—C16	1.513 (3)	C17—H17	0.93
C6—H6	0.98	C18—C19	1.341 (5)
C7—H7	0.95 (4)	C18—H18	0.93
C8—C13	1.363 (4)	C19—C20	1.378 (5)
C8—C9	1.376 (4)	C19—H19	0.93
C9—C10	1.369 (6)	C20—C21	1.393 (4)
C9—H9	0.93	C20—H20	0.93
C10—C11	1.353 (7)	C21—H21	0.93
C7—N1—C2	122.1 (3)	C9—C10—H10	119.8
C7—N1—C6	116.3 (3)	C10—C11—C12	119.8 (4)
C2—N1—C6	121.11 (17)	C10—C11—H11	120.1
N1—C2—C8	111.7 (2)	C12—C11—H11	120.1
N1—C2—C3	108.4 (2)	C11—C12—C13	119.6 (4)
C8—C2—C3	116.8 (2)	C11—C12—H12	120.2
N1—C2—H2	106.4	C13—C12—H12	120.2
C8—C2—H2	106.4	C8—C13—C12	121.0 (3)
C3—C2—H2	106.4	C8—C13—H13	119.5
C4—C3—C2	112.28 (19)	C12—C13—H13	119.5
C4—C3—C14	108.2 (2)	C3—C14—H14A	109.5
C2—C3—C14	111.3 (2)	C3—C14—H14B	109.5
C4—C3—H3	108.3	H14A—C14—H14B	109.5
C2—C3—H3	108.3	C3—C14—H14C	109.5
C14—C3—H3	108.3	H14A—C14—H14C	109.5
O2—C4—C3	120.1 (2)	H14B—C14—H14C	109.5
O2—C4—C5	121.8 (2)	C5—C15—H15A	109.5
C3—C4—C5	118.12 (19)	C5—C15—H15B	109.5
C4—C5—C15	112.6 (2)	H15A—C15—H15B	109.5
C4—C5—C6	112.73 (18)	C5—C15—H15C	109.5
C15—C5—C6	110.8 (2)	H15A—C15—H15C	109.5
C4—C5—H5	106.7	H15B—C15—H15C	109.5
C15—C5—H5	106.7	C21—C16—C17	117.9 (3)
C6—C5—H5	106.7	C21—C16—C6	122.2 (2)
N1—C6—C16	111.6 (2)	C17—C16—C6	119.9 (2)
N1—C6—C5	111.58 (19)	C18—C17—C16	122.1 (3)
C16—C6—C5	112.11 (19)	C18—C17—H17	118.9
N1—C6—H6	107.1	C16—C17—H17	118.9
C16—C6—H6	107.1	C19—C18—C17	119.7 (3)
C5—C6—H6	107.1	C19—C18—H18	120.1
O1—C7—N1	125.8 (5)	C17—C18—H18	120.1
O1—C7—H7	94 (2)	C18—C19—C20	120.5 (3)
N1—C7—H7	140 (2)	C18—C19—H19	119.8
C13—C8—C9	118.1 (3)	C20—C19—H19	119.8
C13—C8—C2	124.9 (2)	C19—C20—C21	119.8 (3)
C9—C8—C2	117.0 (3)	C19—C20—H20	120.1
C10—C9—C8	121.0 (4)	C21—C20—H20	120.1
C10—C9—H9	119.5	C16—C21—C20	120.0 (3)
C8—C9—H9	119.5	C16—C21—H21	120.0
C11—C10—C9	120.4 (4)	C20—C21—H21	120.0
C11—C10—H10	119.8
C7—N1—C2—C8	109.2 (3)	C6—N1—C7—O1	−179.9 (4)
C6—N1—C2—C8	−79.4 (3)	N1—C2—C8—C13	117.9 (3)
C7—N1—C2—C3	−120.7 (3)	C3—C2—C8—C13	−7.7 (4)
C6—N1—C2—C3	50.6 (3)	N1—C2—C8—C9	−62.1 (3)
N1—C2—C3—C4	−51.5 (3)	C3—C2—C8—C9	172.3 (3)
C8—C2—C3—C4	75.6 (3)	C13—C8—C9—C10	−1.2 (5)
N1—C2—C3—C14	69.9 (2)	C2—C8—C9—C10	178.8 (4)
C8—C2—C3—C14	−162.9 (2)	C8—C9—C10—C11	−2.3 (7)
C2—C3—C4—O2	−170.3 (2)	C9—C10—C11—C12	4.3 (8)
C14—C3—C4—O2	66.4 (3)	C10—C11—C12—C13	−2.7 (7)
C2—C3—C4—C5	9.2 (3)	C9—C8—C13—C12	2.7 (5)
C14—C3—C4—C5	−114.1 (2)	C2—C8—C13—C12	−177.3 (3)
O2—C4—C5—C15	−16.0 (3)	C11—C12—C13—C8	−0.8 (6)
C3—C4—C5—C15	164.5 (2)	N1—C6—C16—C21	−66.4 (3)
O2—C4—C5—C6	−142.4 (2)	C5—C6—C16—C21	59.5 (3)
C3—C4—C5—C6	38.2 (3)	N1—C6—C16—C17	114.1 (3)
C7—N1—C6—C16	−65.6 (3)	C5—C6—C16—C17	−120.0 (3)
C2—N1—C6—C16	122.6 (2)	C21—C16—C17—C18	−0.5 (4)
C7—N1—C6—C5	168.1 (3)	C6—C16—C17—C18	179.0 (3)
C2—N1—C6—C5	−3.7 (3)	C16—C17—C18—C19	0.3 (5)
C4—C5—C6—N1	−40.9 (3)	C17—C18—C19—C20	0.2 (6)
C15—C5—C6—N1	−168.1 (2)	C18—C19—C20—C21	−0.5 (6)
C4—C5—C6—C16	−166.8 (2)	C17—C16—C21—C20	0.1 (5)
C15—C5—C6—C16	65.9 (3)	C6—C16—C21—C20	−179.4 (3)
C2—N1—C7—O1	−8.2 (6)	C19—C20—C21—C16	0.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2i	0.98	2.48	3.398 (3)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2i	0.98	2.48	3.398 (3)	156

Symmetry code: (i) .