(1S*,5R*)-9-Phenyl-9-aza-bicyclo-[3.3.1]nonan-3-one.

In the title compound, C(14)H(17)NO, the piperidinone and piperidine rings both adopt a chair conformation. The chiral crystals were obtained from a racemic reaction product via spontaneous resolution.

Related literature

For the synthesis, see: Zhang (2003 ▶). For applications of the compound, see: Vernekar et al. (2010 ▶); Lazny et al. (2011 ▶). For puckering analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C14H17NO

M = 215.29

Orthorhombic,

a = 9.4028 (3) Å

b = 10.2524 (5) Å

c = 12.0473 (6) Å

V = 1161.38 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.40 × 0.40 × 0.35 mm

Data collection

Agilent Xcalibur Eos diffractometer

Absorption correction: multi-scan (ABSPACK in CrysAlis PRO; Agilent, 2011 ▶) T min = 0.918, T max = 1.000

3285 measured reflections

2218 independent reflections

1722 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.092

S = 1.02

2218 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.13 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812020065/fy2049sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812020065/fy2049Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536812020065/fy2049Isup4.cdx

Supplementary material file. DOI: 10.1107/S1600536812020065/fy2049Isup4.cml

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

C14H17NO	Dx = 1.231 Mg m−3
Mr = 215.29	Mo Kα radiation, λ = 0.7107 Å
Orthorhombic, P212121	Cell parameters from 1237 reflections
a = 9.4028 (3) Å	θ = 2.9–29.0°
b = 10.2524 (5) Å	µ = 0.08 mm−1
c = 12.0473 (6) Å	T = 293 K
V = 1161.38 (9) Å3	Block, colourless
Z = 4	0.40 × 0.40 × 0.35 mm
F(000) = 464

Agilent Xcalibur Eos diffractometer	2218 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1722 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.015
Detector resolution: 16.0874 pixels mm-1	θmax = 26.4°, θmin = 2.9°
ω scans	h = −11→7
Absorption correction: multi-scan (ABSPACK in CrysAlis PRO; Agilent, 2011)	k = −9→12
Tmin = 0.918, Tmax = 1.000	l = −8→15
3285 measured reflections

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0394P)2] where P = (Fo2 + 2Fc2)/3
2218 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.13 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	−0.58709 (17)	−0.01586 (16)	−0.68342 (15)	0.0838 (6)
N1	−0.19284 (14)	−0.18245 (14)	−0.65084 (12)	0.0368 (4)
C1	−0.31907 (18)	−0.26416 (18)	−0.63463 (16)	0.0409 (5)
H1	−0.2985	−0.3506	−0.6653	0.049*
C2	−0.4480 (2)	−0.20832 (19)	−0.69713 (16)	0.0472 (5)
H2A	−0.4367	−0.2265	−0.7757	0.057*
H2B	−0.5329	−0.2532	−0.6721	0.057*
C3	−0.4692 (2)	−0.0642 (2)	−0.68231 (16)	0.0510 (6)
C4	−0.3376 (2)	0.01633 (18)	−0.67070 (17)	0.0489 (5)
H4A	−0.3618	0.0971	−0.6332	0.059*
H4B	−0.3032	0.0386	−0.7442	0.059*
C5	−0.2173 (2)	−0.05077 (18)	−0.60634 (17)	0.0412 (5)
H5	−0.1302	0.0001	−0.6174	0.049*
C6	−0.2468 (2)	−0.0573 (2)	−0.48223 (17)	0.0494 (5)
H6A	−0.1612	−0.0854	−0.4442	0.059*
H6B	−0.2703	0.0293	−0.4556	0.059*
C7	−0.3672 (2)	−0.1497 (2)	−0.45334 (16)	0.0522 (6)
H7A	−0.3705	−0.1626	−0.3736	0.063*
H7B	−0.4571	−0.1122	−0.4766	0.063*
C8	−0.3452 (2)	−0.2797 (2)	−0.51068 (17)	0.0510 (5)
H8A	−0.4286	−0.3338	−0.4994	0.061*
H8B	−0.2646	−0.3239	−0.4774	0.061*
C9	−0.11420 (18)	−0.19480 (18)	−0.75009 (15)	0.0363 (4)
C10	−0.1472 (2)	−0.28634 (19)	−0.83142 (16)	0.0435 (5)
H10	−0.2261	−0.3400	−0.8221	0.052*
C11	−0.0647 (2)	−0.2989 (2)	−0.92593 (16)	0.0537 (6)
H11	−0.0896	−0.3602	−0.9794	0.064*
C12	0.0534 (2)	−0.2223 (2)	−0.94206 (16)	0.0597 (6)
H12	0.1084	−0.2308	−1.0058	0.072*
C13	0.0880 (2)	−0.1329 (2)	−0.8617 (2)	0.0605 (6)
H13	0.1680	−0.0807	−0.8712	0.073*
C14	0.0069 (2)	−0.1187 (2)	−0.76732 (18)	0.0497 (5)
H14	0.0333	−0.0574	−0.7142	0.060*

	U11	U22	U33	U12	U13	U23
O1	0.0585 (9)	0.0818 (13)	0.1110 (16)	0.0252 (10)	−0.0147 (10)	0.0074 (12)
N1	0.0385 (8)	0.0357 (8)	0.0362 (9)	−0.0040 (7)	0.0001 (7)	−0.0009 (7)
C1	0.0411 (10)	0.0361 (10)	0.0455 (12)	−0.0027 (9)	0.0024 (9)	0.0022 (9)
C2	0.0401 (10)	0.0537 (12)	0.0478 (13)	−0.0053 (10)	−0.0056 (9)	−0.0027 (11)
C3	0.0514 (12)	0.0589 (13)	0.0428 (13)	0.0091 (12)	−0.0071 (10)	0.0064 (11)
C4	0.0646 (13)	0.0389 (10)	0.0431 (12)	0.0059 (11)	0.0016 (11)	0.0032 (9)
C5	0.0461 (11)	0.0371 (10)	0.0405 (11)	−0.0071 (9)	0.0010 (9)	−0.0024 (9)
C6	0.0536 (11)	0.0577 (13)	0.0370 (12)	0.0021 (11)	−0.0035 (10)	−0.0052 (11)
C7	0.0590 (13)	0.0634 (13)	0.0343 (11)	−0.0013 (11)	0.0053 (10)	0.0057 (10)
C8	0.0501 (12)	0.0536 (12)	0.0494 (12)	−0.0058 (11)	0.0045 (10)	0.0128 (11)
C9	0.0371 (9)	0.0379 (10)	0.0340 (10)	0.0052 (9)	−0.0020 (8)	0.0040 (9)
C10	0.0425 (10)	0.0446 (11)	0.0434 (11)	0.0035 (10)	−0.0026 (9)	−0.0023 (10)
C11	0.0581 (13)	0.0581 (14)	0.0450 (13)	0.0129 (12)	−0.0016 (11)	−0.0081 (11)
C12	0.0618 (14)	0.0737 (16)	0.0436 (13)	0.0145 (13)	0.0173 (12)	0.0027 (12)
C13	0.0533 (13)	0.0651 (15)	0.0630 (16)	−0.0072 (12)	0.0156 (12)	0.0051 (13)
C14	0.0495 (11)	0.0528 (13)	0.0467 (13)	−0.0078 (11)	0.0043 (10)	−0.0023 (10)

O1—C3	1.215 (2)	C6—C7	1.517 (3)
N1—C1	1.466 (2)	C7—H7A	0.9700
N1—C5	1.471 (2)	C7—H7B	0.9700
N1—C9	1.412 (2)	C7—C8	1.516 (3)
C1—H1	0.9800	C8—H8A	0.9700
C1—C2	1.537 (3)	C8—H8B	0.9700
C1—C8	1.522 (3)	C9—C10	1.392 (3)
C2—H2A	0.9700	C9—C14	1.396 (3)
C2—H2B	0.9700	C10—H10	0.9300
C2—C3	1.501 (3)	C10—C11	1.384 (3)
C3—C4	1.494 (3)	C11—H11	0.9300
C4—H4A	0.9700	C11—C12	1.374 (3)
C4—H4B	0.9700	C12—H12	0.9300
C4—C5	1.534 (3)	C12—C13	1.373 (3)
C5—H5	0.9800	C13—H13	0.9300
C5—C6	1.522 (3)	C13—C14	1.376 (3)
C6—H6A	0.9700	C14—H14	0.9300
C6—H6B	0.9700
C1—N1—C5	110.46 (14)	C7—C6—C5	112.88 (17)
C9—N1—C1	119.07 (15)	C7—C6—H6A	109.0
C9—N1—C5	118.22 (14)	C7—C6—H6B	109.0
N1—C1—H1	107.9	C6—C7—H7A	109.6
N1—C1—C2	111.11 (15)	C6—C7—H7B	109.6
N1—C1—C8	108.76 (15)	H7A—C7—H7B	108.2
C2—C1—H1	107.9	C8—C7—C6	110.08 (16)
C8—C1—H1	107.9	C8—C7—H7A	109.6
C8—C1—C2	113.10 (16)	C8—C7—H7B	109.6
C1—C2—H2A	108.7	C1—C8—H8A	109.2
C1—C2—H2B	108.7	C1—C8—H8B	109.2
H2A—C2—H2B	107.6	C7—C8—C1	112.14 (16)
C3—C2—C1	114.39 (17)	C7—C8—H8A	109.2
C3—C2—H2A	108.7	C7—C8—H8B	109.2
C3—C2—H2B	108.7	H8A—C8—H8B	107.9
O1—C3—C2	121.5 (2)	C10—C9—N1	122.68 (16)
O1—C3—C4	122.1 (2)	C10—C9—C14	117.02 (18)
C4—C3—C2	116.42 (18)	C14—C9—N1	120.20 (17)
C3—C4—H4A	108.7	C9—C10—H10	119.4
C3—C4—H4B	108.7	C11—C10—C9	121.13 (19)
C3—C4—C5	114.20 (16)	C11—C10—H10	119.4
H4A—C4—H4B	107.6	C10—C11—H11	119.5
C5—C4—H4A	108.7	C12—C11—C10	121.1 (2)
C5—C4—H4B	108.7	C12—C11—H11	119.5
N1—C5—C4	110.04 (15)	C11—C12—H12	120.9
N1—C5—H5	108.0	C13—C12—C11	118.28 (19)
N1—C5—C6	110.25 (16)	C13—C12—H12	120.9
C4—C5—H5	108.0	C12—C13—H13	119.3
C6—C5—C4	112.44 (16)	C12—C13—C14	121.5 (2)
C6—C5—H5	108.0	C14—C13—H13	119.3
C5—C6—H6A	109.0	C9—C14—H14	119.5
C5—C6—H6B	109.0	C13—C14—C9	121.0 (2)
H6A—C6—H6B	107.8	C13—C14—H14	119.5
O1—C3—C4—C5	146.4 (2)	C5—N1—C1—C2	61.85 (19)
N1—C1—C2—C3	−46.2 (2)	C5—N1—C1—C8	−63.28 (19)
N1—C1—C8—C7	58.9 (2)	C5—N1—C9—C10	−142.12 (17)
N1—C5—C6—C7	−54.0 (2)	C5—N1—C9—C14	41.6 (2)
N1—C9—C10—C11	−177.64 (17)	C5—C6—C7—C8	49.0 (2)
N1—C9—C14—C13	177.52 (18)	C6—C7—C8—C1	−51.6 (2)
C1—N1—C5—C4	−63.47 (19)	C8—C1—C2—C3	76.4 (2)
C1—N1—C5—C6	61.12 (19)	C9—N1—C1—C2	−79.9 (2)
C1—N1—C9—C10	−3.3 (2)	C9—N1—C1—C8	155.02 (16)
C1—N1—C9—C14	−179.62 (16)	C9—N1—C5—C4	78.60 (18)
C1—C2—C3—O1	−148.4 (2)	C9—N1—C5—C6	−156.81 (15)
C1—C2—C3—C4	34.0 (2)	C9—C10—C11—C12	0.7 (3)
C2—C1—C8—C7	−65.0 (2)	C10—C9—C14—C13	1.0 (3)
C2—C3—C4—C5	−35.9 (2)	C10—C11—C12—C13	0.2 (3)
C3—C4—C5—N1	49.8 (2)	C11—C12—C13—C14	−0.4 (3)
C3—C4—C5—C6	−73.5 (2)	C12—C13—C14—C9	−0.2 (3)
C4—C5—C6—C7	69.2 (2)	C14—C9—C10—C11	−1.2 (3)