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

In the title compound, C(21)H(23)NO(2), the piperidine ring adopts a distorted boat conformation. The two phenyl rings form dihedral angles of 64.6 (1) and 87.8 (1)° with the best plane through the piperidine ring. The crystal packing is governed by inter-molecular C-H⋯O inter-actions.

Related literature

For the biological activity of piperidine derivatives, see: Ponnuswamy et al. (2002 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For puckering and asymmetry parameters, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C21H23NO2

M = 321.40

Monoclinic,

a = 7.5622 (4) Å

b = 10.6369 (5) Å

c = 11.1497 (7) Å

β = 100.373 (3)°

V = 882.21 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.977, T max = 0.985

12819 measured reflections

3457 independent reflections

2400 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.145

S = 1.02

3457 reflections

220 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.17 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/S1600536809028049/bt2989sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028049/bt2989Isup2.hkl

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

C21H23NO2	F(000) = 344
Mr = 321.40	Dx = 1.210 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3546 reflections
a = 7.5622 (4) Å	θ = 1.9–34.8°
b = 10.6369 (5) Å	µ = 0.08 mm−1
c = 11.1497 (7) Å	T = 293 K
β = 100.373 (3)°	Block, colorless
V = 882.21 (8) Å3	0.30 × 0.25 × 0.20 mm
Z = 2

Bruker Kappa APEXII area-detector diffractometer	3457 independent reflections
Radiation source: fine-focus sealed tube	2400 reflections with I > 2σ(I)
graphite	Rint = 0.042
ω and φ scans	θmax = 34.8°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −11→11
Tmin = 0.977, Tmax = 0.985	k = −17→11
12819 measured reflections	l = −16→16

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0853P)2] where P = (Fo2 + 2Fc2)/3
3457 reflections	(Δ/σ)max = 0.012
220 parameters	Δρmax = 0.23 e Å−3
1 restraint	Δρmin = −0.17 e Å−3

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	1.0626 (2)	0.57532 (19)	0.23859 (18)	0.0680 (5)
O2	0.4399 (3)	0.3113 (2)	−0.07440 (15)	0.0763 (5)
N1	0.7953 (2)	0.47573 (14)	0.20329 (14)	0.0393 (3)
C2	0.6053 (2)	0.47297 (17)	0.21592 (15)	0.0392 (3)
H2	0.5538	0.5559	0.1928	0.047*
C3	0.4980 (3)	0.3754 (2)	0.13125 (18)	0.0493 (4)
H3A	0.5087	0.2952	0.1735	0.059*
H3B	0.3722	0.3993	0.1187	0.059*
C4	0.5484 (3)	0.3556 (2)	0.00799 (18)	0.0507 (5)
C5	0.7355 (3)	0.3903 (2)	−0.00532 (17)	0.0492 (4)
C6	0.8617 (3)	0.38858 (19)	0.11952 (16)	0.0414 (4)
H6	0.9759	0.4240	0.1055	0.050*
C7	0.9060 (3)	0.57188 (19)	0.25158 (18)	0.0464 (4)
C8	0.8306 (4)	0.6735 (2)	0.3207 (2)	0.0600 (5)
H8A	0.7347	0.7155	0.2675	0.090*
H8B	0.9234	0.7330	0.3509	0.090*
H8C	0.7852	0.6371	0.3879	0.090*
C9	0.5778 (2)	0.44554 (17)	0.34515 (16)	0.0406 (4)
C10	0.6819 (3)	0.3583 (2)	0.41885 (18)	0.0508 (4)
H10	0.7759	0.3178	0.3912	0.061*
C11	0.6462 (4)	0.3315 (2)	0.5329 (2)	0.0606 (6)
H11	0.7158	0.2726	0.5819	0.073*
C12	0.5085 (4)	0.3913 (3)	0.5744 (2)	0.0670 (7)
H12	0.4851	0.3732	0.6517	0.080*
C13	0.4058 (4)	0.4773 (3)	0.5026 (3)	0.0726 (7)
H13	0.3123	0.5175	0.5310	0.087*
C14	0.4399 (3)	0.5051 (2)	0.3878 (2)	0.0571 (5)
H14	0.3696	0.5641	0.3393	0.069*
C15	0.7232 (4)	0.5268 (2)	−0.0542 (2)	0.0616 (6)
H15A	0.6699	0.5795	−0.0005	0.092*
H15B	0.6505	0.5286	−0.1341	0.092*
H15C	0.8416	0.5571	−0.0581	0.092*
C16	0.8096 (4)	0.3069 (3)	−0.0963 (2)	0.0699 (7)
H16A	0.7373	0.3168	−0.1758	0.105*
H16B	0.8067	0.2206	−0.0714	0.105*
H16C	0.9313	0.3308	−0.0988	0.105*
C17	0.9083 (2)	0.26144 (18)	0.17969 (16)	0.0417 (4)
C18	0.8065 (3)	0.1533 (2)	0.1580 (2)	0.0525 (5)
H18	0.7036	0.1538	0.0981	0.063*
C19	0.8543 (4)	0.0441 (2)	0.2235 (2)	0.0634 (6)
H19	0.7835	−0.0276	0.2077	0.076*
C20	1.0062 (4)	0.0418 (2)	0.3117 (2)	0.0654 (6)
H20	1.0375	−0.0309	0.3570	0.079*
C21	1.1104 (3)	0.1459 (3)	0.3327 (2)	0.0600 (6)
H21	1.2149	0.1434	0.3912	0.072*
C22	1.0634 (3)	0.2562 (2)	0.26817 (18)	0.0500 (4)
H22	1.1360	0.3270	0.2842	0.060*

	U11	U22	U33	U12	U13	U23
O1	0.0472 (8)	0.0620 (10)	0.0923 (12)	−0.0134 (8)	0.0056 (8)	0.0097 (9)
O2	0.0845 (12)	0.0894 (13)	0.0451 (9)	−0.0115 (11)	−0.0149 (8)	−0.0095 (9)
N1	0.0402 (7)	0.0397 (7)	0.0373 (7)	−0.0037 (6)	0.0051 (6)	0.0018 (6)
C2	0.0390 (8)	0.0421 (8)	0.0349 (8)	−0.0003 (7)	0.0023 (6)	0.0005 (6)
C3	0.0429 (9)	0.0589 (12)	0.0433 (10)	−0.0061 (8)	−0.0001 (7)	−0.0048 (8)
C4	0.0613 (12)	0.0512 (10)	0.0343 (9)	0.0020 (9)	−0.0058 (8)	0.0008 (7)
C5	0.0658 (12)	0.0487 (10)	0.0327 (8)	0.0094 (9)	0.0081 (8)	0.0039 (7)
C6	0.0429 (8)	0.0453 (9)	0.0368 (8)	0.0025 (7)	0.0093 (7)	0.0054 (7)
C7	0.0499 (10)	0.0398 (9)	0.0456 (9)	−0.0071 (8)	−0.0018 (8)	0.0104 (7)
C8	0.0766 (14)	0.0449 (11)	0.0548 (12)	−0.0111 (10)	0.0022 (10)	−0.0039 (9)
C9	0.0403 (8)	0.0428 (9)	0.0387 (8)	−0.0052 (7)	0.0069 (7)	−0.0029 (7)
C10	0.0585 (11)	0.0520 (10)	0.0434 (10)	0.0020 (9)	0.0134 (8)	0.0051 (8)
C11	0.0724 (14)	0.0623 (13)	0.0475 (11)	−0.0077 (11)	0.0120 (10)	0.0099 (10)
C12	0.0712 (14)	0.0869 (17)	0.0465 (11)	−0.0237 (13)	0.0207 (11)	−0.0022 (11)
C13	0.0619 (13)	0.0986 (19)	0.0638 (15)	−0.0010 (15)	0.0287 (12)	−0.0103 (14)
C14	0.0493 (10)	0.0683 (14)	0.0547 (12)	0.0055 (10)	0.0118 (9)	−0.0031 (10)
C15	0.0848 (16)	0.0563 (12)	0.0443 (11)	0.0116 (11)	0.0129 (11)	0.0159 (9)
C16	0.0966 (19)	0.0713 (14)	0.0444 (12)	0.0180 (14)	0.0198 (12)	−0.0011 (11)
C17	0.0436 (9)	0.0458 (9)	0.0364 (8)	0.0071 (8)	0.0093 (7)	0.0044 (7)
C18	0.0543 (11)	0.0496 (10)	0.0504 (11)	0.0035 (9)	0.0011 (9)	0.0042 (8)
C19	0.0725 (14)	0.0477 (12)	0.0696 (15)	0.0031 (11)	0.0117 (12)	0.0106 (10)
C20	0.0843 (16)	0.0561 (13)	0.0573 (13)	0.0203 (12)	0.0163 (12)	0.0162 (10)
C21	0.0579 (12)	0.0752 (15)	0.0446 (11)	0.0216 (11)	0.0027 (9)	0.0064 (10)
C22	0.0463 (10)	0.0573 (11)	0.0460 (10)	0.0080 (9)	0.0068 (8)	0.0006 (9)

O1—C7	1.219 (3)	C11—C12	1.370 (4)
O2—C4	1.211 (3)	C11—H11	0.9300
N1—C7	1.369 (2)	C12—C13	1.362 (4)
N1—C6	1.467 (2)	C12—H12	0.9300
N1—C2	1.469 (2)	C13—C14	1.383 (4)
C2—C9	1.521 (2)	C13—H13	0.9300
C2—C3	1.534 (3)	C14—H14	0.9300
C2—H2	0.9800	C15—H15A	0.9600
C3—C4	1.506 (3)	C15—H15B	0.9600
C3—H3A	0.9700	C15—H15C	0.9600
C3—H3B	0.9700	C16—H16A	0.9600
C4—C5	1.495 (3)	C16—H16B	0.9600
C5—C16	1.528 (3)	C16—H16C	0.9600
C5—C6	1.540 (3)	C17—C18	1.381 (3)
C5—C15	1.548 (3)	C17—C22	1.391 (3)
C6—C17	1.523 (3)	C18—C19	1.385 (3)
C6—H6	0.9800	C18—H18	0.9300
C7—C8	1.499 (3)	C19—C20	1.371 (4)
C8—H8A	0.9600	C19—H19	0.9300
C8—H8B	0.9600	C20—C21	1.355 (4)
C8—H8C	0.9600	C20—H20	0.9300
C9—C14	1.376 (3)	C21—C22	1.389 (3)
C9—C10	1.387 (3)	C21—H21	0.9300
C10—C11	1.376 (3)	C22—H22	0.9300
C10—H10	0.9300
C7—N1—C6	117.82 (15)	C9—C10—H10	120.0
C7—N1—C2	121.12 (15)	C12—C11—C10	120.3 (2)
C6—N1—C2	120.09 (15)	C12—C11—H11	119.9
N1—C2—C9	113.43 (14)	C10—C11—H11	119.9
N1—C2—C3	111.90 (14)	C13—C12—C11	120.0 (2)
C9—C2—C3	107.80 (15)	C13—C12—H12	120.0
N1—C2—H2	107.8	C11—C12—H12	120.0
C9—C2—H2	107.8	C12—C13—C14	120.4 (2)
C3—C2—H2	107.8	C12—C13—H13	119.8
C4—C3—C2	117.60 (17)	C14—C13—H13	119.8
C4—C3—H3A	107.9	C9—C14—C13	120.0 (2)
C2—C3—H3A	107.9	C9—C14—H14	120.0
C4—C3—H3B	107.9	C13—C14—H14	120.0
C2—C3—H3B	107.9	C5—C15—H15A	109.5
H3A—C3—H3B	107.2	C5—C15—H15B	109.5
O2—C4—C5	123.0 (2)	H15A—C15—H15B	109.5
O2—C4—C3	119.9 (2)	C5—C15—H15C	109.5
C5—C4—C3	117.11 (17)	H15A—C15—H15C	109.5
C4—C5—C16	112.9 (2)	H15B—C15—H15C	109.5
C4—C5—C6	110.54 (15)	C5—C16—H16A	109.5
C16—C5—C6	110.58 (18)	C5—C16—H16B	109.5
C4—C5—C15	105.60 (19)	H16A—C16—H16B	109.5
C16—C5—C15	108.50 (18)	C5—C16—H16C	109.5
C6—C5—C15	108.51 (18)	H16A—C16—H16C	109.5
N1—C6—C17	111.05 (14)	H16B—C16—H16C	109.5
N1—C6—C5	109.90 (15)	C18—C17—C22	117.57 (18)
C17—C6—C5	117.75 (17)	C18—C17—C6	125.84 (17)
N1—C6—H6	105.7	C22—C17—C6	116.52 (18)
C17—C6—H6	105.7	C17—C18—C19	121.5 (2)
C5—C6—H6	105.7	C17—C18—H18	119.3
O1—C7—N1	120.9 (2)	C19—C18—H18	119.3
O1—C7—C8	120.5 (2)	C20—C19—C18	119.9 (2)
N1—C7—C8	118.58 (18)	C20—C19—H19	120.1
C7—C8—H8A	109.5	C18—C19—H19	120.1
C7—C8—H8B	109.5	C21—C20—C19	119.7 (2)
H8A—C8—H8B	109.5	C21—C20—H20	120.1
C7—C8—H8C	109.5	C19—C20—H20	120.1
H8A—C8—H8C	109.5	C20—C21—C22	121.0 (2)
H8B—C8—H8C	109.5	C20—C21—H21	119.5
C14—C9—C10	119.22 (17)	C22—C21—H21	119.5
C14—C9—C2	118.71 (18)	C21—C22—C17	120.4 (2)
C10—C9—C2	122.00 (16)	C21—C22—H22	119.8
C11—C10—C9	120.1 (2)	C17—C22—H22	119.8
C11—C10—H10	120.0
C7—N1—C2—C9	−70.9 (2)	C6—N1—C7—C8	170.20 (17)
C6—N1—C2—C9	120.55 (17)	C2—N1—C7—C8	1.4 (3)
C7—N1—C2—C3	166.82 (16)	N1—C2—C9—C14	143.64 (19)
C6—N1—C2—C3	−1.7 (2)	C3—C2—C9—C14	−91.9 (2)
N1—C2—C3—C4	−35.4 (2)	N1—C2—C9—C10	−39.4 (2)
C9—C2—C3—C4	−160.78 (17)	C3—C2—C9—C10	85.1 (2)
C2—C3—C4—O2	−157.6 (2)	C14—C9—C10—C11	0.4 (3)
C2—C3—C4—C5	23.6 (3)	C2—C9—C10—C11	−176.5 (2)
O2—C4—C5—C16	−31.1 (3)	C9—C10—C11—C12	−0.4 (4)
C3—C4—C5—C16	147.7 (2)	C10—C11—C12—C13	0.3 (4)
O2—C4—C5—C6	−155.5 (2)	C11—C12—C13—C14	−0.2 (4)
C3—C4—C5—C6	23.3 (3)	C10—C9—C14—C13	−0.3 (3)
O2—C4—C5—C15	87.3 (3)	C2—C9—C14—C13	176.7 (2)
C3—C4—C5—C15	−93.9 (2)	C12—C13—C14—C9	0.2 (4)
C7—N1—C6—C17	107.34 (18)	N1—C6—C17—C18	104.0 (2)
C2—N1—C6—C17	−83.8 (2)	C5—C6—C17—C18	−23.9 (3)
C7—N1—C6—C5	−120.60 (18)	N1—C6—C17—C22	−73.0 (2)
C2—N1—C6—C5	48.3 (2)	C5—C6—C17—C22	159.13 (16)
C4—C5—C6—N1	−58.1 (2)	C22—C17—C18—C19	1.4 (3)
C16—C5—C6—N1	176.13 (18)	C6—C17—C18—C19	−175.6 (2)
C15—C5—C6—N1	57.2 (2)	C17—C18—C19—C20	−0.3 (4)
C4—C5—C6—C17	70.3 (2)	C18—C19—C20—C21	−1.2 (4)
C16—C5—C6—C17	−55.4 (2)	C19—C20—C21—C22	1.6 (4)
C15—C5—C6—C17	−174.30 (17)	C20—C21—C22—C17	−0.5 (3)
C6—N1—C7—O1	−9.6 (3)	C18—C17—C22—C21	−1.0 (3)
C2—N1—C7—O1	−178.35 (18)	C6—C17—C22—C21	176.26 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1	0.98	2.21	2.700 (3)	110
C8—H8A···O2i	0.96	2.53	3.442 (3)	159
C14—H14···O1ii	0.93	2.39	3.124 (3)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O2i	0.96	2.53	3.442 (3)	159
C14—H14⋯O1ii	0.93	2.39	3.124 (3)	135

Symmetry codes: (i) ; (ii) .