2,4-Bis(4-fluoro-phen-yl)-3-aza-bicyclo-[3.3.1]nonan-9-one.

In the title compound, C(20)H(19)F(2)NO, a crystallographic mirror plane bis-ects the mol-ecule, passing through the N, O and two C atoms of the central ring system. The mol-ecule exists in a twin-chair conformation with equatorial dispositions of the 4-fluoro-phenyl groups on both sides of the secondary amino groups; the dihedral angle between the aromatic ring planes is 28.67 (3)°.

Related literature

For chemical background, see: Buxton & Roberts (1996 ▶); Evans & Seddon (1997 ▶); Ramachandran et al. (2007 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C20H19F2NO

M = 327.36

Orthorhombic,

a = 7.6153 (3) Å

b = 21.1392 (9) Å

c = 10.0878 (4) Å

V = 1623.95 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 (2) K

0.35 × 0.32 × 0.30 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.967, T max = 0.971

11360 measured reflections

2064 independent reflections

1596 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.141

S = 0.91

2064 reflections

118 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.19 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..

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808024744/hb2763sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024744/hb2763Isup2.hkl

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

C20H19F2NO	F(000) = 688
Mr = 327.36	Dx = 1.339 Mg m−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 4451 reflections
a = 7.6153 (3) Å	θ = 3.4–28.0°
b = 21.1392 (9) Å	µ = 0.10 mm−1
c = 10.0878 (4) Å	T = 298 K
V = 1623.95 (11) Å3	Block, colourless
Z = 4	0.35 × 0.32 × 0.30 mm

Bruker APEXII CCD diffractometer	2064 independent reflections
Radiation source: fine-focus sealed tube	1596 reflections with I > 2σ(I)
graphite	Rint = 0.020
ω scans	θmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −8→10
Tmin = 0.967, Tmax = 0.971	k = −28→28
11360 measured reflections	l = −13→12

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 0.91	w = 1/[σ2(Fo2) + (0.0897P)2 + 0.3733P] where P = (Fo2 + 2Fc2)/3
2064 reflections	(Δ/σ)max < 0.001
118 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.19 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	0.92315 (17)	0.30735 (5)	0.39201 (12)	0.0391 (3)
H1	0.8839	0.3055	0.2996	0.047*
C2	0.75726 (16)	0.30901 (5)	0.48153 (14)	0.0421 (3)
H2	0.6864	0.3460	0.4576	0.051*
C3	0.79266 (19)	0.31054 (6)	0.63140 (13)	0.0473 (3)
H3A	0.8701	0.3458	0.6508	0.057*
H3B	0.6827	0.3181	0.6773	0.057*
C4	0.8751 (3)	0.2500	0.68562 (18)	0.0492 (4)
H4A	0.9993	0.2500	0.6644	0.059*
H4B	0.8642	0.2500	0.7814	0.059*
C5	0.6527 (2)	0.2500	0.45348 (18)	0.0435 (4)
C6	1.03437 (17)	0.36590 (5)	0.40791 (12)	0.0400 (3)
C7	0.9916 (2)	0.41937 (6)	0.33533 (16)	0.0543 (4)
H7	0.8976	0.4179	0.2766	0.065*
C8	1.0856 (2)	0.47481 (7)	0.34848 (19)	0.0666 (5)
H8	1.0550	0.5107	0.3003	0.080*
C9	1.2238 (2)	0.47573 (7)	0.4334 (2)	0.0643 (5)
C10	1.2733 (2)	0.42414 (8)	0.50616 (19)	0.0641 (4)
H10	1.3688	0.4261	0.5634	0.077*
C11	1.1771 (2)	0.36882 (7)	0.49220 (15)	0.0519 (4)
H11	1.2091	0.3331	0.5404	0.062*
F1	1.31755 (17)	0.53023 (5)	0.44594 (17)	0.1030 (5)
H111	1.121 (3)	0.2500	0.369 (2)	0.047 (5)*
N1	1.0241 (2)	0.2500	0.41923 (15)	0.0384 (3)
O1	0.50237 (19)	0.2500	0.41536 (17)	0.0626 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0441 (7)	0.0372 (6)	0.0359 (6)	0.0013 (5)	−0.0009 (5)	0.0021 (4)
C2	0.0395 (6)	0.0368 (6)	0.0500 (7)	0.0045 (5)	−0.0010 (5)	0.0018 (5)
C3	0.0493 (7)	0.0465 (7)	0.0461 (7)	−0.0017 (6)	0.0077 (6)	−0.0072 (5)
C4	0.0529 (10)	0.0585 (10)	0.0361 (9)	0.000	0.0003 (8)	0.000
C5	0.0384 (9)	0.0483 (9)	0.0437 (9)	0.000	−0.0027 (7)	0.000
C6	0.0440 (7)	0.0352 (5)	0.0406 (6)	0.0016 (5)	0.0073 (5)	0.0021 (4)
C7	0.0567 (8)	0.0455 (7)	0.0605 (8)	0.0048 (6)	0.0044 (7)	0.0137 (6)
C8	0.0694 (10)	0.0390 (7)	0.0915 (12)	0.0051 (7)	0.0242 (10)	0.0157 (7)
C9	0.0586 (9)	0.0382 (7)	0.0961 (13)	−0.0091 (6)	0.0292 (9)	−0.0104 (7)
C10	0.0558 (9)	0.0579 (9)	0.0787 (11)	−0.0105 (7)	0.0011 (8)	−0.0110 (8)
C11	0.0529 (8)	0.0455 (7)	0.0572 (8)	−0.0038 (6)	−0.0029 (6)	0.0043 (6)
F1	0.0834 (8)	0.0474 (6)	0.1782 (14)	−0.0225 (5)	0.0323 (8)	−0.0170 (6)
N1	0.0377 (8)	0.0341 (7)	0.0434 (8)	0.000	0.0057 (6)	0.000
O1	0.0421 (8)	0.0693 (10)	0.0763 (11)	0.000	−0.0159 (7)	0.000

C1—N1	1.4613 (14)	C5—C2i	1.5067 (15)
C1—C6	1.5083 (16)	C6—C11	1.381 (2)
C1—C2	1.5533 (18)	C6—C7	1.3856 (17)
C1—H1	0.9800	C7—C8	1.380 (2)
C2—C5	1.5067 (15)	C7—H7	0.9300
C2—C3	1.536 (2)	C8—C9	1.357 (3)
C2—H2	0.9800	C8—H8	0.9300
C3—C4	1.5266 (17)	C9—F1	1.3613 (17)
C3—H3A	0.9700	C9—C10	1.367 (3)
C3—H3B	0.9700	C10—C11	1.387 (2)
C4—C3i	1.5266 (17)	C10—H10	0.9300
C4—H4A	0.9700	C11—H11	0.9300
C4—H4B	0.9700	N1—C1i	1.4613 (14)
C5—O1	1.208 (2)	N1—H111	0.89 (2)
N1—C1—C6	111.44 (10)	O1—C5—C2	124.12 (7)
N1—C1—C2	109.70 (10)	O1—C5—C2i	124.12 (7)
C6—C1—C2	112.11 (9)	C2—C5—C2i	111.76 (14)
N1—C1—H1	107.8	C11—C6—C7	118.28 (12)
C6—C1—H1	107.8	C11—C6—C1	122.96 (11)
C2—C1—H1	107.8	C7—C6—C1	118.76 (12)
C5—C2—C3	107.16 (11)	C8—C7—C6	121.34 (15)
C5—C2—C1	107.58 (11)	C8—C7—H7	119.3
C3—C2—C1	115.47 (11)	C6—C7—H7	119.3
C5—C2—H2	108.8	C9—C8—C7	118.37 (14)
C3—C2—H2	108.8	C9—C8—H8	120.8
C1—C2—H2	108.8	C7—C8—H8	120.8
C4—C3—C2	114.02 (11)	C8—C9—F1	118.51 (16)
C4—C3—H3A	108.7	C8—C9—C10	122.75 (14)
C2—C3—H3A	108.7	F1—C9—C10	118.74 (18)
C4—C3—H3B	108.7	C9—C10—C11	118.19 (16)
C2—C3—H3B	108.7	C9—C10—H10	120.9
H3A—C3—H3B	107.6	C11—C10—H10	120.9
C3i—C4—C3	113.91 (16)	C6—C11—C10	121.05 (14)
C3i—C4—H4A	108.8	C6—C11—H11	119.5
C3—C4—H4A	108.8	C10—C11—H11	119.5
C3i—C4—H4B	108.8	C1i—N1—C1	112.11 (14)
C3—C4—H4B	108.8	C1i—N1—H111	109.1 (7)
H4A—C4—H4B	107.7	C1—N1—H111	109.1 (7)
N1—C1—C2—C5	−58.02 (14)	C2—C1—C6—C7	−84.10 (15)
C6—C1—C2—C5	177.61 (10)	C11—C6—C7—C8	−1.5 (2)
N1—C1—C2—C3	61.57 (13)	C1—C6—C7—C8	178.21 (13)
C6—C1—C2—C3	−62.80 (13)	C6—C7—C8—C9	0.9 (2)
C5—C2—C3—C4	52.64 (16)	C7—C8—C9—F1	179.55 (15)
C1—C2—C3—C4	−67.17 (15)	C7—C8—C9—C10	0.0 (3)
C2—C3—C4—C3i	−43.3 (2)	C8—C9—C10—C11	−0.2 (3)
C3—C2—C5—O1	113.4 (2)	F1—C9—C10—C11	−179.77 (15)
C1—C2—C5—O1	−121.84 (19)	C7—C6—C11—C10	1.3 (2)
C3—C2—C5—C2i	−65.39 (17)	C1—C6—C11—C10	−178.44 (14)
C1—C2—C5—C2i	59.35 (18)	C9—C10—C11—C6	−0.4 (2)
N1—C1—C6—C11	−27.77 (17)	C6—C1—N1—C1i	−174.53 (8)
C2—C1—C6—C11	95.62 (15)	C2—C1—N1—C1i	60.72 (16)
N1—C1—C6—C7	152.51 (13)