1-(2-Azido-acet-yl)-3-methyl-2,6-diphenyl-piperidin-4-one.

In the title compound, C(20)H(20)N(4)O(2), the piperidine ring adopts a distorted boat conformation. The two phenyl rings form dihedral angles of 82.87 (1) and 84.40 (1)° with respect to the piperidine ring. The crystal packing is stabilized by inter-molecular C-H⋯O and C-H⋯N inter-actions.

Related literature

For the biological activity of piperidines, see: Aridoss et al. (2008 ▶, 2010 ▶). For ring conformational analysis, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶). For related structures, see: Jeyaraman et al. (1999 ▶); Keana & Cai (1990 ▶); Ponnuswamy et al. (2002 ▶).

Experimental

Crystal data

C20H20N4O2

M = 348.40

Monoclinic,

a = 11.0418 (3) Å

b = 15.7844 (5) Å

c = 10.5684 (3) Å

β = 108.458 (2)°

V = 1747.19 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 292 K

0.25 × 0.23 × 0.2 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.978, T max = 0.983

16435 measured reflections

4286 independent reflections

3147 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.138

S = 1.05

4286 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.18 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/S1600536810039097/bt5365sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810039097/bt5365Isup2.hkl

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

C20H20N4O2	F(000) = 736
Mr = 348.40	Dx = 1.324 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1520 reflections
a = 11.0418 (3) Å	θ = 1.9–28.5°
b = 15.7844 (5) Å	µ = 0.09 mm−1
c = 10.5684 (3) Å	T = 292 K
β = 108.458 (2)°	Block, colourless
V = 1747.19 (9) Å3	0.25 × 0.23 × 0.2 mm
Z = 4

Bruker SMART APEXII area-detector diffractometer	4286 independent reflections
Radiation source: fine-focus sealed tube	3147 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω and φ scans	θmax = 28.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −14→14
Tmin = 0.978, Tmax = 0.983	k = −19→21
16435 measured reflections	l = −14→13

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0678P)2 + 0.3241P] where P = (Fo2 + 2Fc2)/3
4286 reflections	(Δ/σ)max < 0.001
236 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.18 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
C1	0.59213 (13)	0.02968 (9)	0.33092 (13)	0.0366 (3)
H1	0.5050	0.0521	0.3073	0.044*
C2	0.57944 (14)	−0.06647 (9)	0.32572 (15)	0.0411 (3)
H2A	0.5489	−0.0853	0.3976	0.049*
H2B	0.5166	−0.0827	0.2421	0.049*
C3	0.70355 (14)	−0.10988 (9)	0.33785 (14)	0.0392 (3)
C4	0.80956 (13)	−0.05375 (9)	0.32448 (14)	0.0386 (3)
H4	0.8441	−0.0228	0.4087	0.046*
C5	0.75819 (13)	0.01278 (9)	0.21275 (13)	0.0360 (3)
H5	0.7324	−0.0182	0.1281	0.043*
C6	0.86401 (14)	0.07294 (9)	0.20829 (14)	0.0387 (3)
C7	0.92891 (16)	0.12263 (10)	0.31632 (17)	0.0498 (4)
H7	0.9025	0.1239	0.3916	0.060*
C8	1.03309 (18)	0.17048 (12)	0.3130 (2)	0.0638 (5)
H8	1.0764	0.2034	0.3863	0.077*
C9	1.07271 (18)	0.16958 (12)	0.2027 (2)	0.0661 (5)
H9	1.1430	0.2015	0.2012	0.079*
C10	1.00821 (19)	0.12146 (13)	0.0946 (2)	0.0670 (5)
H10	1.0341	0.1211	0.0190	0.080*
C11	0.90476 (17)	0.07345 (11)	0.09768 (17)	0.0536 (4)
H11	0.8617	0.0408	0.0238	0.064*
C12	0.91822 (16)	−0.10347 (11)	0.30249 (19)	0.0556 (4)
H12A	0.9447	−0.1471	0.3688	0.083*
H12B	0.9887	−0.0661	0.3093	0.083*
H12C	0.8903	−0.1287	0.2154	0.083*
C13	0.66501 (13)	0.06839 (9)	0.46567 (14)	0.0386 (3)
C14	0.70059 (15)	0.02104 (11)	0.58243 (15)	0.0489 (4)
H14	0.6877	−0.0373	0.5783	0.059*
C15	0.75481 (18)	0.05956 (14)	0.70438 (17)	0.0639 (5)
H15	0.7784	0.0269	0.7816	0.077*
C16	0.77431 (18)	0.14548 (15)	0.71305 (19)	0.0683 (6)
H16	0.8088	0.1713	0.7958	0.082*
C17	0.74226 (18)	0.19344 (12)	0.5977 (2)	0.0645 (5)
H17	0.7572	0.2515	0.6025	0.077*
C18	0.68785 (16)	0.15484 (10)	0.47485 (17)	0.0506 (4)
H18	0.6664	0.1874	0.3976	0.061*
C19	0.56623 (15)	0.09208 (9)	0.10767 (14)	0.0416 (3)
C20	0.43631 (16)	0.12667 (11)	0.10659 (16)	0.0531 (4)
H20A	0.3892	0.0822	0.1339	0.064*
H20B	0.4493	0.1726	0.1705	0.064*
N1	0.64214 (11)	0.05607 (7)	0.22287 (11)	0.0364 (3)
N2	0.36126 (14)	0.15755 (9)	−0.02523 (14)	0.0570 (4)
N3	0.38863 (12)	0.22845 (9)	−0.05698 (13)	0.0475 (3)
N4	0.39979 (17)	0.29178 (11)	−0.09966 (16)	0.0670 (4)
O1	0.71688 (12)	−0.18542 (7)	0.35828 (12)	0.0547 (3)
O2	0.59960 (12)	0.09701 (8)	0.00863 (11)	0.0566 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0380 (7)	0.0361 (7)	0.0357 (7)	0.0033 (5)	0.0116 (6)	0.0017 (6)
C2	0.0417 (7)	0.0383 (8)	0.0434 (8)	−0.0047 (6)	0.0138 (6)	−0.0010 (6)
C3	0.0512 (8)	0.0315 (7)	0.0369 (7)	0.0001 (6)	0.0168 (6)	0.0005 (6)
C4	0.0421 (7)	0.0328 (7)	0.0418 (8)	0.0028 (5)	0.0146 (6)	0.0015 (6)
C5	0.0416 (7)	0.0327 (7)	0.0337 (7)	−0.0015 (5)	0.0119 (6)	−0.0024 (5)
C6	0.0421 (7)	0.0339 (7)	0.0391 (7)	−0.0004 (5)	0.0114 (6)	0.0043 (6)
C7	0.0534 (9)	0.0450 (9)	0.0493 (9)	−0.0079 (7)	0.0137 (7)	−0.0027 (7)
C8	0.0559 (10)	0.0492 (10)	0.0768 (13)	−0.0137 (8)	0.0077 (9)	−0.0012 (9)
C9	0.0519 (10)	0.0532 (10)	0.0941 (15)	−0.0071 (8)	0.0244 (10)	0.0206 (10)
C10	0.0680 (12)	0.0710 (13)	0.0728 (13)	−0.0020 (10)	0.0375 (11)	0.0185 (10)
C11	0.0605 (10)	0.0582 (10)	0.0459 (9)	−0.0059 (8)	0.0222 (8)	0.0021 (7)
C12	0.0505 (9)	0.0487 (9)	0.0719 (11)	0.0104 (7)	0.0254 (9)	0.0090 (8)
C13	0.0379 (7)	0.0405 (8)	0.0376 (7)	0.0066 (5)	0.0124 (6)	−0.0014 (6)
C14	0.0516 (9)	0.0536 (10)	0.0410 (8)	0.0025 (7)	0.0139 (7)	0.0029 (7)
C15	0.0606 (11)	0.0864 (15)	0.0393 (9)	0.0048 (9)	0.0083 (8)	0.0006 (9)
C16	0.0568 (10)	0.0925 (16)	0.0474 (10)	0.0053 (10)	0.0049 (8)	−0.0255 (10)
C17	0.0606 (11)	0.0529 (10)	0.0714 (13)	0.0038 (8)	0.0087 (9)	−0.0231 (9)
C18	0.0559 (9)	0.0409 (8)	0.0501 (9)	0.0066 (7)	0.0099 (7)	−0.0051 (7)
C19	0.0483 (8)	0.0361 (7)	0.0344 (7)	−0.0034 (6)	0.0044 (6)	−0.0004 (6)
C20	0.0542 (9)	0.0537 (10)	0.0445 (9)	0.0093 (7)	0.0057 (7)	0.0037 (7)
N1	0.0403 (6)	0.0343 (6)	0.0330 (6)	0.0011 (5)	0.0093 (5)	0.0010 (5)
N2	0.0614 (8)	0.0418 (8)	0.0505 (8)	0.0023 (6)	−0.0070 (7)	0.0026 (6)
N3	0.0451 (7)	0.0496 (8)	0.0402 (7)	0.0029 (6)	0.0029 (6)	−0.0050 (6)
N4	0.0798 (11)	0.0576 (10)	0.0584 (10)	−0.0084 (8)	0.0145 (8)	0.0053 (8)
O1	0.0714 (8)	0.0328 (6)	0.0688 (8)	0.0034 (5)	0.0347 (6)	0.0067 (5)
O2	0.0614 (7)	0.0684 (8)	0.0369 (6)	0.0013 (6)	0.0112 (5)	0.0091 (5)

C1—N1	1.4771 (17)	C10—H10	0.9300
C1—C2	1.5235 (19)	C11—H11	0.9300
C1—C13	1.5243 (19)	C12—H12A	0.9600
C1—H1	0.9800	C12—H12B	0.9600
C2—C3	1.501 (2)	C12—H12C	0.9600
C2—H2A	0.9700	C13—C18	1.386 (2)
C2—H2B	0.9700	C13—C14	1.389 (2)
C3—O1	1.2123 (16)	C14—C15	1.379 (2)
C3—C4	1.510 (2)	C14—H14	0.9300
C4—C12	1.512 (2)	C15—C16	1.372 (3)
C4—C5	1.5476 (19)	C15—H15	0.9300
C4—H4	0.9800	C16—C17	1.383 (3)
C5—N1	1.4856 (17)	C16—H16	0.9300
C5—C6	1.5179 (19)	C17—C18	1.387 (2)
C5—H5	0.9800	C17—H17	0.9300
C6—C11	1.379 (2)	C18—H18	0.9300
C6—C7	1.384 (2)	C19—O2	1.2172 (18)
C7—C8	1.386 (2)	C19—N1	1.3645 (18)
C7—H7	0.9300	C19—C20	1.532 (2)
C8—C9	1.369 (3)	C20—N2	1.461 (2)
C8—H8	0.9300	C20—H20A	0.9700
C9—C10	1.369 (3)	C20—H20B	0.9700
C9—H9	0.9300	N2—N3	1.233 (2)
C10—C11	1.380 (3)	N3—N4	1.119 (2)
N1—C1—C2	107.80 (11)	C10—C11—C6	121.20 (17)
N1—C1—C13	113.16 (11)	C10—C11—H11	119.4
C2—C1—C13	116.63 (12)	C6—C11—H11	119.4
N1—C1—H1	106.2	C4—C12—H12A	109.5
C2—C1—H1	106.2	C4—C12—H12B	109.5
C13—C1—H1	106.2	H12A—C12—H12B	109.5
C3—C2—C1	112.38 (12)	C4—C12—H12C	109.5
C3—C2—H2A	109.1	H12A—C12—H12C	109.5
C1—C2—H2A	109.1	H12B—C12—H12C	109.5
C3—C2—H2B	109.1	C18—C13—C14	118.28 (14)
C1—C2—H2B	109.1	C18—C13—C1	119.39 (13)
H2A—C2—H2B	107.9	C14—C13—C1	122.12 (13)
O1—C3—C2	121.36 (13)	C15—C14—C13	120.68 (17)
O1—C3—C4	122.66 (13)	C15—C14—H14	119.7
C2—C3—C4	115.97 (11)	C13—C14—H14	119.7
C3—C4—C12	112.72 (12)	C16—C15—C14	120.73 (18)
C3—C4—C5	111.22 (12)	C16—C15—H15	119.6
C12—C4—C5	110.61 (12)	C14—C15—H15	119.6
C3—C4—H4	107.3	C15—C16—C17	119.44 (17)
C12—C4—H4	107.3	C15—C16—H16	120.3
C5—C4—H4	107.3	C17—C16—H16	120.3
N1—C5—C6	113.86 (11)	C16—C17—C18	119.93 (18)
N1—C5—C4	111.92 (10)	C16—C17—H17	120.0
C6—C5—C4	110.39 (11)	C18—C17—H17	120.0
N1—C5—H5	106.7	C17—C18—C13	120.90 (17)
C6—C5—H5	106.7	C17—C18—H18	119.6
C4—C5—H5	106.7	C13—C18—H18	119.6
C11—C6—C7	118.25 (14)	O2—C19—N1	121.75 (14)
C11—C6—C5	119.41 (13)	O2—C19—C20	120.57 (13)
C7—C6—C5	122.12 (13)	N1—C19—C20	117.68 (13)
C6—C7—C8	120.36 (16)	N2—C20—C19	111.92 (14)
C6—C7—H7	119.8	N2—C20—H20A	109.2
C8—C7—H7	119.8	C19—C20—H20A	109.2
C9—C8—C7	120.50 (18)	N2—C20—H20B	109.2
C9—C8—H8	119.8	C19—C20—H20B	109.2
C7—C8—H8	119.8	H20A—C20—H20B	107.9
C8—C9—C10	119.64 (16)	C19—N1—C1	122.20 (12)
C8—C9—H9	120.2	C19—N1—C5	115.31 (11)
C10—C9—H9	120.2	C1—N1—C5	117.91 (10)
C9—C10—C11	120.04 (17)	N3—N2—C20	116.64 (14)
C9—C10—H10	120.0	N4—N3—N2	171.04 (17)
C11—C10—H10	120.0
N1—C1—C2—C3	57.25 (15)	N1—C1—C13—C14	−135.96 (14)
C13—C1—C2—C3	−71.29 (15)	C2—C1—C13—C14	−10.06 (19)
C1—C2—C3—O1	167.38 (13)	C18—C13—C14—C15	1.3 (2)
C1—C2—C3—C4	−12.02 (17)	C1—C13—C14—C15	−173.35 (14)
O1—C3—C4—C12	15.3 (2)	C13—C14—C15—C16	0.3 (3)
C2—C3—C4—C12	−165.33 (13)	C14—C15—C16—C17	−1.7 (3)
O1—C3—C4—C5	140.15 (14)	C15—C16—C17—C18	1.6 (3)
C2—C3—C4—C5	−40.45 (16)	C16—C17—C18—C13	−0.1 (3)
C3—C4—C5—N1	47.54 (15)	C14—C13—C18—C17	−1.4 (2)
C12—C4—C5—N1	173.60 (12)	C1—C13—C18—C17	173.41 (14)
C3—C4—C5—C6	175.48 (11)	O2—C19—C20—N2	4.4 (2)
C12—C4—C5—C6	−58.46 (16)	N1—C19—C20—N2	−175.73 (13)
N1—C5—C6—C11	−118.49 (15)	O2—C19—N1—C1	−163.94 (13)
C4—C5—C6—C11	114.64 (15)	C20—C19—N1—C1	16.16 (19)
N1—C5—C6—C7	67.05 (17)	O2—C19—N1—C5	−8.5 (2)
C4—C5—C6—C7	−59.82 (18)	C20—C19—N1—C5	171.63 (12)
C11—C6—C7—C8	−0.9 (2)	C2—C1—N1—C19	104.11 (14)
C5—C6—C7—C8	173.64 (15)	C13—C1—N1—C19	−125.40 (13)
C6—C7—C8—C9	0.4 (3)	C2—C1—N1—C5	−50.76 (15)
C7—C8—C9—C10	0.5 (3)	C13—C1—N1—C5	79.74 (14)
C8—C9—C10—C11	−0.7 (3)	C6—C5—N1—C19	76.01 (15)
C9—C10—C11—C6	0.2 (3)	C4—C5—N1—C19	−157.92 (12)
C7—C6—C11—C10	0.6 (2)	C6—C5—N1—C1	−127.41 (12)
C5—C6—C11—C10	−174.06 (16)	C4—C5—N1—C1	−1.34 (16)
N1—C1—C13—C18	49.44 (17)	C19—C20—N2—N3	−79.48 (19)
C2—C1—C13—C18	175.34 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1i	0.93	2.57	3.464 (2)	162
C5—H5···N2ii	0.98	2.52	3.353 (2)	142
C2—H2B···O2ii	0.97	2.56	3.4933 (19)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O1i	0.93	2.57	3.464 (2)	162
C5—H5⋯N2ii	0.98	2.52	3.353 (2)	142
C2—H2B⋯O2ii	0.97	2.56	3.4933 (19)	161

Symmetry codes: (i) ; (ii) .