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

The title compound, C(20)H(19)F(2)NO, exhibits a chair-chair conformation, with the aryl groups in the heterocycle in equatorial orientations and oriented at an angle of 33.35 (3)° to one another. A crystallographic mirror plane, passing through the N atom, the C and O atoms of the carbonyl group and the C atom in the 7-position, bis-ects the mol-ecule. The mol-ecular structure is stabilized by one C-H⋯N inter-action and the crystal structure is stabilized by a weak C-H⋯π inter-action.

Related literature

For related literature, see: Barker et al. (2005 ▶); Dunitz et al. (1997 ▶); Evans et al. (1997 ▶); Jeyaraman et al. (1981 ▶); Padegimas et al. (1972 ▶); Smith-Verdier et al. (1983 ▶); Web et al. (1967 ▶); Wiechert et al. (1997 ▶); Cremer & Pople (1975 ▶); Ramachandran et al. (2007 ▶); Vijayalakshmi et al. (2000 ▶).

Experimental

Crystal data

C20H19F2NO

M = 327.36

Orthorhombic,

a = 7.3844 (2) Å

b = 21.5172 (10) Å

c = 10.2608 (4) Å

V = 1630.36 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 (2) K

0.35 × 0.19 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.967, T max = 0.986

11640 measured reflections

2069 independent reflections

1507 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.154

S = 1.03

2069 reflections

118 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker–Nonius, 2004 ▶); cell refinement: APEX2; data reduction: SAINT-Plus (Bruker–Nonius, 2004 ▶); 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/S1600536808024690/bx2166sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024690/bx2166Isup2.hkl

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

C20H19F2NO	F000 = 688
Mr = 327.36	Dx = 1.334 Mg m−3
Orthorhombic, Pnma	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 3860 reflections
a = 7.3844 (2) Å	θ = 2.2–27.8º
b = 21.5172 (10) Å	µ = 0.10 mm−1
c = 10.2608 (4) Å	T = 298 (2) K
V = 1630.36 (11) Å3	Needle, colourless
Z = 4	0.35 × 0.19 × 0.15 mm

Bruker APEXII CCD area-detector diffractometer	2069 independent reflections
Radiation source: fine-focus sealed tube	1507 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.023
T = 298(2) K	θmax = 28.3º
φ and ω scans	θmin = 1.9º
Absorption correction: multi-scan(SADABS; Bruker, 1999)	h = −9→9
Tmin = 0.967, Tmax = 0.986	k = −28→27
11640 measured reflections	l = −13→13

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)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.154	w = 1/[σ2(Fo2) + (0.0736P)2 + 0.4778P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2069 reflections	Δρmax = 0.27 e Å−3
118 parameters	Δρmin = −0.25 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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 andgoodness of fit S are based on F2, conventional R-factors R are basedon F, with F set to zero for negative F2. The threshold expression ofF2 > σ(F2) is used only for calculating R-factors(gt) etc. and isnot relevant to the choice of reflections for refinement. R-factors basedon 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	0.9282 (2)	0.30645 (7)	0.60735 (13)	0.0415 (4)
H1	0.8910	0.3052	0.6990	0.050*
C2	0.75387 (19)	0.30789 (7)	0.52202 (15)	0.0444 (4)
H2	0.6813	0.3441	0.5468	0.053*
C3	0.7856 (2)	0.30939 (8)	0.37344 (15)	0.0482 (4)
H3A	0.6707	0.3166	0.3302	0.058*
H3B	0.8646	0.3441	0.3529	0.058*
C4	0.8693 (3)	0.2500	0.3196 (2)	0.0501 (6)
H4A	0.8565	0.2500	0.2255	0.060*
H4B	0.9978	0.2500	0.3394	0.060*
C5	0.6479 (3)	0.2500	0.5518 (2)	0.0460 (5)
C6	1.0432 (2)	0.36362 (7)	0.58774 (14)	0.0436 (4)
C7	1.1855 (2)	0.36471 (8)	0.49973 (17)	0.0509 (4)
H7	1.2153	0.3294	0.4522	0.061*
C8	1.2815 (2)	0.41854 (9)	0.4838 (2)	0.0603 (5)
C9	1.2457 (3)	0.47171 (9)	0.5505 (2)	0.0723 (6)
H9	1.3139	0.5075	0.5371	0.087*
C10	1.1056 (3)	0.47077 (9)	0.6385 (2)	0.0767 (7)
H10	1.0775	0.5065	0.6853	0.092*
C11	1.0059 (3)	0.41717 (8)	0.65820 (19)	0.0599 (5)
H11	0.9128	0.4170	0.7193	0.072*
F1	1.42123 (18)	0.41845 (6)	0.39681 (15)	0.0962 (5)
N1	1.0305 (2)	0.2500	0.57975 (17)	0.0395 (4)
O1	0.4936 (2)	0.2500	0.59191 (18)	0.0638 (5)
H1A	1.127 (3)	0.2500	0.629 (2)	0.047 (6)*

	U11	U22	U33	U12	U13	U23
C1	0.0426 (8)	0.0480 (9)	0.0338 (7)	0.0033 (6)	0.0003 (6)	−0.0020 (6)
C2	0.0364 (7)	0.0515 (10)	0.0454 (8)	0.0071 (6)	0.0012 (6)	−0.0016 (7)
C3	0.0432 (8)	0.0592 (10)	0.0423 (8)	−0.0006 (7)	−0.0067 (6)	0.0080 (7)
C4	0.0439 (11)	0.0734 (16)	0.0331 (10)	0.000	−0.0014 (9)	0.000
C5	0.0361 (11)	0.0656 (15)	0.0362 (10)	0.000	0.0020 (8)	0.000
C6	0.0450 (8)	0.0426 (9)	0.0431 (7)	0.0051 (6)	−0.0104 (6)	−0.0028 (6)
C7	0.0511 (9)	0.0455 (9)	0.0560 (9)	−0.0018 (7)	−0.0026 (7)	−0.0016 (7)
C8	0.0528 (10)	0.0552 (11)	0.0731 (12)	−0.0072 (8)	−0.0096 (9)	0.0110 (9)
C9	0.0659 (12)	0.0455 (11)	0.1056 (17)	−0.0076 (9)	−0.0312 (12)	0.0070 (11)
C10	0.0815 (14)	0.0464 (11)	0.1024 (16)	0.0107 (10)	−0.0309 (13)	−0.0217 (11)
C11	0.0610 (10)	0.0555 (11)	0.0632 (10)	0.0109 (8)	−0.0095 (9)	−0.0158 (8)
F1	0.0816 (9)	0.0895 (10)	0.1176 (11)	−0.0267 (7)	0.0191 (8)	0.0147 (8)
N1	0.0367 (9)	0.0412 (10)	0.0407 (9)	0.000	−0.0063 (7)	0.000
O1	0.0408 (9)	0.0867 (14)	0.0639 (11)	0.000	0.0146 (8)	0.000

C1—N1	1.4585 (17)	C5—C2i	1.5025 (19)
C1—C6	1.508 (2)	C6—C7	1.386 (2)
C1—C2	1.557 (2)	C6—C11	1.388 (2)
C1—H1	0.9800	C7—C8	1.368 (2)
C2—C5	1.5025 (19)	C7—H7	0.9300
C2—C3	1.543 (2)	C8—C9	1.359 (3)
C2—H2	0.9800	C8—F1	1.364 (2)
C3—C4	1.523 (2)	C9—C10	1.373 (3)
C3—H3A	0.9700	C9—H9	0.9300
C3—H3B	0.9700	C10—C11	1.383 (3)
C4—C3i	1.523 (2)	C10—H10	0.9300
C4—H4A	0.9700	C11—H11	0.9300
C4—H4B	0.9700	N1—C1i	1.4585 (17)
C5—O1	1.212 (2)	N1—H1A	0.87 (2)
N1—C1—C6	111.20 (12)	O1—C5—C2	123.98 (8)
N1—C1—C2	109.63 (12)	O1—C5—C2i	123.98 (8)
C6—C1—C2	111.97 (12)	C2—C5—C2i	112.01 (17)
N1—C1—H1	108.0	C7—C6—C11	118.42 (16)
C6—C1—H1	108.0	C7—C6—C1	121.85 (13)
C2—C1—H1	108.0	C11—C6—C1	119.73 (15)
C5—C2—C3	107.30 (14)	C8—C7—C6	119.02 (16)
C5—C2—C1	107.44 (13)	C8—C7—H7	120.5
C3—C2—C1	115.49 (12)	C6—C7—H7	120.5
C5—C2—H2	108.8	C9—C8—F1	118.52 (17)
C3—C2—H2	108.8	C9—C8—C7	123.5 (2)
C1—C2—H2	108.8	F1—C8—C7	117.96 (17)
C4—C3—C2	113.73 (14)	C8—C9—C10	117.71 (19)
C4—C3—H3A	108.8	C8—C9—H9	121.1
C2—C3—H3A	108.8	C10—C9—H9	121.1
C4—C3—H3B	108.8	C9—C10—C11	120.63 (18)
C2—C3—H3B	108.8	C9—C10—H10	119.7
H3A—C3—H3B	107.7	C11—C10—H10	119.7
C3i—C4—C3	114.07 (18)	C10—C11—C6	120.68 (19)
C3i—C4—H4A	108.7	C10—C11—H11	119.7
C3—C4—H4A	108.7	C6—C11—H11	119.7
C3i—C4—H4B	108.7	C1i—N1—C1	112.78 (16)
C3—C4—H4B	108.7	C1i—N1—H1A	108.1 (8)
H4A—C4—H4B	107.6	C1—N1—H1A	108.1 (8)
N1—C1—C2—C5	57.58 (16)	C2—C1—C6—C11	84.78 (17)
C6—C1—C2—C5	−178.52 (13)	C11—C6—C7—C8	−1.2 (2)
N1—C1—C2—C3	−62.09 (17)	C1—C6—C7—C8	178.18 (15)
C6—C1—C2—C3	61.81 (17)	C6—C7—C8—C9	0.4 (3)
C5—C2—C3—C4	−52.65 (18)	C6—C7—C8—F1	179.86 (15)
C1—C2—C3—C4	67.10 (18)	F1—C8—C9—C10	−179.43 (17)
C2—C3—C4—C3i	44.0 (2)	C7—C8—C9—C10	0.1 (3)
C3—C2—C5—O1	−113.3 (2)	C8—C9—C10—C11	0.4 (3)
C1—C2—C5—O1	122.0 (2)	C9—C10—C11—C6	−1.2 (3)
C3—C2—C5—C2i	65.0 (2)	C7—C6—C11—C10	1.6 (3)
C1—C2—C5—C2i	−59.8 (2)	C1—C6—C11—C10	−177.76 (16)
N1—C1—C6—C7	28.45 (19)	C6—C1—N1—C1i	175.53 (10)
C2—C1—C6—C7	−94.57 (16)	C2—C1—N1—C1i	−60.11 (18)
N1—C1—C6—C11	−152.20 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4B···N1	0.97	2.48	2.923 (3)	108
C11—H11···Cg1ii	0.93	2.93	3.862 (2)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4B⋯N1	0.97	2.48	2.923 (3)	108
C11—H11⋯Cg1i	0.93	2.93	3.862 (2)	175

Symmetry code: (i) . Cg1 is the centroid of the C6–C11 ring.