c-3,t-3-Dimethyl-4-oxo-r-2,c-6-diphenyl-piperidine-1-carboxamide.

In the title compound, C(26)H(26)N(2)O(2), the piperidinone ring adopts a distorted boat conformation. The two phenyl rings substituted at positions 2 and 6 of the piperidinone ring occupy axial and equatorial orientations, which are approximately perpendicular to each other [89.14 (8)°]. The phenyl-carbamoyl group adopts an extended conformation. The crystal structure is stabilized by inter-molecular C-H⋯O inter-actions.

Related literature

For general background to the pharmaceutical activity of piperidine derivatives, see: Mobio et al. (1989 ▶); Palani et al. (2002 ▶). For hybridization, see: Beddoes et al. (1986 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For ring conformational analysis, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C26H26N2O2

M = 398.49

Triclinic,

a = 9.6648 (2) Å

b = 10.7938 (3) Å

c = 11.4233 (3) Å

α = 101.303 (2)°

β = 90.158 (1)°

γ = 113.191 (1)°

V = 1069.91 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.12 × 0.12 × 0.10 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.991, T max = 0.992

26776 measured reflections

6362 independent reflections

4483 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.129

S = 1.03

6362 reflections

278 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (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: 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/S1600536809041579/bt5059sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041579/bt5059Isup2.hkl

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

C26H26N2O2	Z = 2
Mr = 398.49	F(000) = 424
Triclinic, P1	Dx = 1.237 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6648 (2) Å	Cell parameters from 6362 reflections
b = 10.7938 (3) Å	θ = 2.1–30.3°
c = 11.4233 (3) Å	µ = 0.08 mm−1
α = 101.303 (2)°	T = 293 K
β = 90.158 (1)°	Block, colourless
γ = 113.191 (1)°	0.12 × 0.12 × 0.10 mm
V = 1069.91 (5) Å3

Bruker Kappa APEXII area-detector diffractometer	6362 independent reflections
Radiation source: fine-focus sealed tube	4483 reflections with I > 2σ(I)
graphite	Rint = 0.027
ω and φ scans	θmax = 30.3°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −13→13
Tmin = 0.991, Tmax = 0.992	k = −15→15
26776 measured reflections	l = −16→16

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)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.129	w = 1/[σ2(Fo2) + (0.0562P)2 + 0.1478P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.010
6362 reflections	Δρmax = 0.23 e Å−3
278 parameters	Δρmin = −0.16 e Å−3
1 restraint	Extinction correction: SHELXS97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.034 (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 > 2sigma(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
C2	0.44729 (12)	0.65312 (11)	0.17958 (10)	0.0397 (2)
H2	0.4661	0.5889	0.1148	0.048*
C3	0.27465 (12)	0.60768 (12)	0.17189 (11)	0.0464 (3)
C4	0.23264 (13)	0.71273 (13)	0.25470 (11)	0.0482 (3)
C5	0.34974 (13)	0.85807 (13)	0.28686 (12)	0.0486 (3)
H5A	0.3981	0.8718	0.3656	0.058*
H5B	0.2979	0.9197	0.2936	0.058*
C6	0.47423 (12)	0.90306 (11)	0.20204 (10)	0.0414 (2)
H6	0.4324	0.9268	0.1356	0.050*
C7	0.60634 (12)	0.79834 (11)	0.05299 (10)	0.0397 (2)
C8	0.78032 (12)	0.96713 (11)	−0.05439 (10)	0.0404 (2)
C9	0.77964 (15)	0.88317 (13)	−0.16236 (11)	0.0503 (3)
H9	0.7057	0.7938	−0.1843	0.060*
C10	0.89077 (17)	0.93379 (15)	−0.23770 (13)	0.0628 (4)
H10	0.8916	0.8770	−0.3101	0.075*
C11	0.99929 (16)	1.06556 (15)	−0.20790 (14)	0.0628 (4)
H11	1.0729	1.0980	−0.2596	0.075*
C12	0.99842 (15)	1.14898 (14)	−0.10158 (14)	0.0582 (3)
H12	1.0711	1.2390	−0.0812	0.070*
C13	0.89053 (14)	1.10043 (12)	−0.02441 (11)	0.0485 (3)
H13	0.8916	1.1575	0.0484	0.058*
C14	0.52831 (12)	0.64977 (11)	0.29232 (10)	0.0419 (2)
C15	0.48157 (15)	0.66344 (14)	0.40654 (12)	0.0550 (3)
H15	0.3888	0.6690	0.4183	0.066*
C16	0.5715 (2)	0.66892 (17)	0.50407 (14)	0.0684 (4)
H16	0.5387	0.6785	0.5805	0.082*
C17	0.70797 (18)	0.66035 (16)	0.48857 (15)	0.0683 (4)
H17	0.7680	0.6646	0.5543	0.082*
C18	0.75602 (15)	0.64543 (15)	0.37601 (15)	0.0630 (4)
H18	0.8486	0.6392	0.3651	0.076*
C19	0.66678 (13)	0.63960 (13)	0.27891 (13)	0.0510 (3)
H19	0.6999	0.6286	0.2027	0.061*
C20	0.19496 (16)	0.46380 (14)	0.19745 (15)	0.0632 (4)
H20A	0.2215	0.4659	0.2791	0.095*
H20B	0.2257	0.4003	0.1447	0.095*
H20C	0.0876	0.4347	0.1847	0.095*
C21	0.22210 (16)	0.60584 (16)	0.04407 (13)	0.0628 (4)
H21A	0.1147	0.5793	0.0374	0.094*
H21B	0.2470	0.5409	−0.0124	0.094*
H21C	0.2718	0.6962	0.0275	0.094*
C22	0.60341 (13)	1.03354 (12)	0.26859 (11)	0.0474 (3)
C23	0.70016 (15)	1.02965 (15)	0.35611 (12)	0.0587 (3)
H23	0.6878	0.9455	0.3737	0.070*
C24	0.81482 (18)	1.1497 (2)	0.41752 (16)	0.0796 (5)
H24	0.8786	1.1460	0.4766	0.095*
C25	0.8349 (2)	1.27372 (19)	0.3918 (2)	0.0935 (6)
H25	0.9122	1.3543	0.4334	0.112*
C26	0.7412 (2)	1.27938 (16)	0.3048 (2)	0.0903 (6)
H26	0.7558	1.3639	0.2870	0.108*
C27	0.62430 (18)	1.15950 (14)	0.24296 (15)	0.0664 (4)
H27	0.5603	1.1640	0.1845	0.080*
N1	0.52148 (10)	0.79071 (9)	0.15014 (8)	0.0386 (2)
N2	0.67000 (12)	0.92692 (11)	0.02715 (9)	0.0469 (2)
O1	0.62406 (11)	0.69939 (9)	−0.00520 (8)	0.0565 (2)
O2	0.11166 (10)	0.68212 (11)	0.29595 (10)	0.0686 (3)
H2A	0.6752 (17)	0.9942 (16)	0.0847 (14)	0.061 (4)*

	U11	U22	U33	U12	U13	U23
C2	0.0345 (5)	0.0362 (5)	0.0476 (6)	0.0130 (4)	0.0116 (4)	0.0097 (4)
C3	0.0332 (5)	0.0434 (6)	0.0576 (7)	0.0109 (4)	0.0071 (5)	0.0091 (5)
C4	0.0336 (5)	0.0558 (7)	0.0562 (7)	0.0185 (5)	0.0092 (5)	0.0132 (5)
C5	0.0407 (6)	0.0486 (6)	0.0588 (7)	0.0219 (5)	0.0163 (5)	0.0078 (5)
C6	0.0381 (5)	0.0406 (5)	0.0475 (6)	0.0186 (4)	0.0088 (4)	0.0081 (4)
C7	0.0360 (5)	0.0403 (5)	0.0425 (5)	0.0149 (4)	0.0079 (4)	0.0090 (4)
C8	0.0395 (5)	0.0421 (6)	0.0443 (6)	0.0190 (5)	0.0088 (4)	0.0145 (4)
C9	0.0519 (7)	0.0447 (6)	0.0498 (6)	0.0154 (5)	0.0129 (5)	0.0084 (5)
C10	0.0709 (9)	0.0624 (8)	0.0555 (8)	0.0271 (7)	0.0264 (7)	0.0123 (6)
C11	0.0537 (8)	0.0642 (9)	0.0750 (9)	0.0229 (7)	0.0297 (7)	0.0265 (7)
C12	0.0436 (7)	0.0491 (7)	0.0772 (9)	0.0112 (5)	0.0121 (6)	0.0187 (6)
C13	0.0466 (6)	0.0443 (6)	0.0531 (7)	0.0171 (5)	0.0063 (5)	0.0099 (5)
C14	0.0374 (5)	0.0363 (5)	0.0525 (6)	0.0135 (4)	0.0101 (5)	0.0134 (4)
C15	0.0532 (7)	0.0634 (8)	0.0559 (7)	0.0281 (6)	0.0154 (6)	0.0192 (6)
C16	0.0810 (10)	0.0730 (10)	0.0530 (8)	0.0312 (8)	0.0074 (7)	0.0168 (7)
C17	0.0655 (9)	0.0618 (9)	0.0740 (10)	0.0196 (7)	−0.0122 (7)	0.0197 (7)
C18	0.0425 (7)	0.0569 (8)	0.0917 (11)	0.0185 (6)	0.0011 (7)	0.0237 (7)
C19	0.0410 (6)	0.0506 (7)	0.0660 (8)	0.0195 (5)	0.0136 (5)	0.0199 (6)
C20	0.0460 (7)	0.0478 (7)	0.0863 (10)	0.0084 (6)	0.0184 (7)	0.0154 (7)
C21	0.0466 (7)	0.0664 (9)	0.0634 (8)	0.0150 (6)	−0.0062 (6)	0.0037 (7)
C22	0.0423 (6)	0.0429 (6)	0.0523 (6)	0.0161 (5)	0.0160 (5)	0.0012 (5)
C23	0.0482 (7)	0.0603 (8)	0.0567 (7)	0.0163 (6)	0.0078 (6)	0.0002 (6)
C24	0.0541 (8)	0.0866 (10)	0.0687 (10)	0.0134 (8)	0.0045 (7)	−0.0170 (8)
C25	0.0692 (11)	0.0643 (9)	0.1014 (14)	0.0008 (8)	0.0184 (10)	−0.0282 (8)
C26	0.0941 (13)	0.0401 (8)	0.1177 (16)	0.0155 (8)	0.0353 (12)	−0.0011 (8)
C27	0.0710 (9)	0.0430 (7)	0.0821 (10)	0.0227 (6)	0.0206 (8)	0.0062 (6)
N1	0.0362 (4)	0.0361 (4)	0.0446 (5)	0.0151 (4)	0.0113 (4)	0.0094 (4)
N2	0.0549 (6)	0.0398 (5)	0.0472 (5)	0.0194 (4)	0.0190 (4)	0.0108 (4)
O1	0.0640 (6)	0.0426 (5)	0.0640 (5)	0.0224 (4)	0.0311 (4)	0.0117 (4)
O2	0.0388 (5)	0.0738 (7)	0.0890 (7)	0.0197 (4)	0.0237 (5)	0.0137 (5)

C2—N1	1.4802 (13)	C14—C15	1.3816 (17)
C2—C14	1.5193 (16)	C14—C19	1.3917 (16)
C2—C3	1.5395 (15)	C15—C16	1.389 (2)
C2—H2	0.9800	C15—H15	0.9300
C3—C4	1.5132 (17)	C16—C17	1.368 (2)
C3—C20	1.5256 (18)	C16—H16	0.9300
C3—C21	1.5384 (19)	C17—C18	1.370 (2)
C4—O2	1.2075 (14)	C17—H17	0.9300
C4—C5	1.5001 (17)	C18—C19	1.379 (2)
C5—C6	1.5339 (15)	C18—H18	0.9300
C5—H5A	0.9700	C19—H19	0.9300
C5—H5B	0.9700	C20—H20A	0.9600
C6—N1	1.4786 (13)	C20—H20B	0.9600
C6—C22	1.5201 (16)	C20—H20C	0.9600
C6—H6	0.9800	C21—H21A	0.9600
C7—O1	1.2159 (13)	C21—H21B	0.9600
C7—N2	1.3715 (15)	C21—H21C	0.9600
C7—N1	1.3779 (13)	C22—C27	1.3839 (19)
C8—C9	1.3783 (16)	C22—C23	1.385 (2)
C8—C13	1.3856 (16)	C23—C24	1.381 (2)
C8—N2	1.4115 (14)	C23—H23	0.9300
C9—C10	1.3856 (17)	C24—C25	1.366 (3)
C9—H9	0.9300	C24—H24	0.9300
C10—C11	1.368 (2)	C25—C26	1.369 (3)
C10—H10	0.9300	C25—H25	0.9300
C11—C12	1.365 (2)	C26—C27	1.392 (2)
C11—H11	0.9300	C26—H26	0.9300
C12—C13	1.3765 (18)	C27—H27	0.9300
C12—H12	0.9300	N2—H2A	0.864 (16)
C13—H13	0.9300
N1—C2—C14	109.54 (9)	C14—C15—C16	120.74 (13)
N1—C2—C3	110.26 (9)	C14—C15—H15	119.6
C14—C2—C3	119.32 (9)	C16—C15—H15	119.6
N1—C2—H2	105.6	C17—C16—C15	120.48 (14)
C14—C2—H2	105.6	C17—C16—H16	119.8
C3—C2—H2	105.6	C15—C16—H16	119.8
C4—C3—C20	111.63 (10)	C16—C17—C18	119.82 (14)
C4—C3—C21	106.12 (11)	C16—C17—H17	120.1
C20—C3—C21	109.08 (11)	C18—C17—H17	120.1
C4—C3—C2	110.60 (9)	C17—C18—C19	119.84 (13)
C20—C3—C2	111.34 (10)	C17—C18—H18	120.1
C21—C3—C2	107.87 (10)	C19—C18—H18	120.1
O2—C4—C5	120.53 (11)	C18—C19—C14	121.52 (13)
O2—C4—C3	122.26 (11)	C18—C19—H19	119.2
C5—C4—C3	117.19 (9)	C14—C19—H19	119.2
C4—C5—C6	117.78 (10)	C3—C20—H20A	109.5
C4—C5—H5A	107.9	C3—C20—H20B	109.5
C6—C5—H5A	107.9	H20A—C20—H20B	109.5
C4—C5—H5B	107.9	C3—C20—H20C	109.5
C6—C5—H5B	107.9	H20A—C20—H20C	109.5
H5A—C5—H5B	107.2	H20B—C20—H20C	109.5
N1—C6—C22	113.61 (9)	C3—C21—H21A	109.5
N1—C6—C5	112.05 (9)	C3—C21—H21B	109.5
C22—C6—C5	108.49 (9)	H21A—C21—H21B	109.5
N1—C6—H6	107.5	C3—C21—H21C	109.5
C22—C6—H6	107.5	H21A—C21—H21C	109.5
C5—C6—H6	107.5	H21B—C21—H21C	109.5
O1—C7—N2	122.47 (10)	C27—C22—C23	118.93 (13)
O1—C7—N1	122.90 (10)	C27—C22—C6	119.72 (13)
N2—C7—N1	114.63 (9)	C23—C22—C6	121.35 (12)
C9—C8—C13	119.39 (10)	C24—C23—C22	120.53 (16)
C9—C8—N2	123.48 (10)	C24—C23—H23	119.7
C13—C8—N2	117.08 (10)	C22—C23—H23	119.7
C8—C9—C10	119.03 (12)	C25—C24—C23	120.28 (19)
C8—C9—H9	120.5	C25—C24—H24	119.9
C10—C9—H9	120.5	C23—C24—H24	119.9
C11—C10—C9	121.42 (13)	C24—C25—C26	119.99 (16)
C11—C10—H10	119.3	C24—C25—H25	120.0
C9—C10—H10	119.3	C26—C25—H25	120.0
C12—C11—C10	119.36 (12)	C25—C26—C27	120.40 (18)
C12—C11—H11	120.3	C25—C26—H26	119.8
C10—C11—H11	120.3	C27—C26—H26	119.8
C11—C12—C13	120.31 (12)	C22—C27—C26	119.87 (18)
C11—C12—H12	119.8	C22—C27—H27	120.1
C13—C12—H12	119.8	C26—C27—H27	120.1
C12—C13—C8	120.47 (12)	C7—N1—C6	121.29 (9)
C12—C13—H13	119.8	C7—N1—C2	116.56 (8)
C8—C13—H13	119.8	C6—N1—C2	120.31 (8)
C15—C14—C19	117.59 (12)	C7—N2—C8	125.58 (9)
C15—C14—C2	126.22 (10)	C7—N2—H2A	115.1 (10)
C19—C14—C2	116.09 (10)	C8—N2—H2A	113.3 (10)
N1—C2—C3—C4	−57.33 (13)	C16—C17—C18—C19	0.2 (2)
C14—C2—C3—C4	70.71 (13)	C17—C18—C19—C14	0.6 (2)
N1—C2—C3—C20	177.95 (10)	C15—C14—C19—C18	−1.17 (18)
C14—C2—C3—C20	−54.01 (14)	C2—C14—C19—C18	175.36 (11)
N1—C2—C3—C21	58.31 (12)	N1—C6—C22—C27	129.49 (12)
C14—C2—C3—C21	−173.65 (10)	C5—C6—C22—C27	−105.18 (13)
C20—C3—C4—O2	−29.31 (18)	N1—C6—C22—C23	−51.43 (14)
C21—C3—C4—O2	89.41 (15)	C5—C6—C22—C23	73.89 (13)
C2—C3—C4—O2	−153.86 (13)	C27—C22—C23—C24	0.55 (19)
C20—C3—C4—C5	149.20 (12)	C6—C22—C23—C24	−178.53 (12)
C21—C3—C4—C5	−92.08 (13)	C22—C23—C24—C25	−0.6 (2)
C2—C3—C4—C5	24.65 (15)	C23—C24—C25—C26	0.0 (3)
O2—C4—C5—C6	−158.95 (12)	C24—C25—C26—C27	0.7 (3)
C3—C4—C5—C6	22.51 (17)	C23—C22—C27—C26	0.1 (2)
C4—C5—C6—N1	−36.49 (15)	C6—C22—C27—C26	179.15 (13)
C4—C5—C6—C22	−162.73 (11)	C25—C26—C27—C22	−0.7 (2)
C13—C8—C9—C10	0.85 (19)	O1—C7—N1—C6	−166.29 (11)
N2—C8—C9—C10	178.19 (12)	N2—C7—N1—C6	13.92 (15)
C8—C9—C10—C11	−1.0 (2)	O1—C7—N1—C2	−1.72 (16)
C9—C10—C11—C12	0.1 (2)	N2—C7—N1—C2	178.49 (10)
C10—C11—C12—C13	0.8 (2)	C22—C6—N1—C7	−71.04 (14)
C11—C12—C13—C8	−0.9 (2)	C5—C6—N1—C7	165.56 (10)
C9—C8—C13—C12	0.09 (19)	C22—C6—N1—C2	124.96 (11)
N2—C8—C13—C12	−177.42 (12)	C5—C6—N1—C2	1.56 (14)
N1—C2—C14—C15	100.75 (13)	C14—C2—N1—C7	107.12 (10)
C3—C2—C14—C15	−27.62 (17)	C3—C2—N1—C7	−119.65 (10)
N1—C2—C14—C19	−75.44 (12)	C14—C2—N1—C6	−88.14 (11)
C3—C2—C14—C19	156.19 (10)	C3—C2—N1—C6	45.08 (13)
C19—C14—C15—C16	1.00 (19)	O1—C7—N2—C8	−10.60 (19)
C2—C14—C15—C16	−175.14 (12)	N1—C7—N2—C8	169.19 (11)
C14—C15—C16—C17	−0.2 (2)	C9—C8—N2—C7	39.03 (18)
C15—C16—C17—C18	−0.4 (2)	C13—C8—N2—C7	−143.58 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O2i	0.93	2.56	3.4488 (17)	161
C20—H20B···O1ii	0.96	2.52	3.4520 (17)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯O2i	0.93	2.56	3.4488 (17)	161
C20—H20B⋯O1ii	0.96	2.52	3.4520 (17)	162

Symmetry codes: (i) ; (ii) .