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

The title compound, C(20)H(19)F(2)NO, exists in a twin-chair conformation with an equatorial orientation of the two 2-fluoro-phenyl groups on both sides of the secondary amine group. The benzene rings are orientated at an angle of 25.68 (4)° with respect to one another and the F atoms point upwards (towards the carbonyl group). The crystal is stabilized by an inter-molecular N-H⋯π inter-action.

Related literature

3-Aza­bicyclo­nona­nes are present in numerous naturally occurring diterpenoid/norditerpenoid alkaloids and display broad-spectrum biological activity, see: Hardick et al. (1996 ▶); Jeyaraman et al. (1981 ▶); For related structures, see: Parthiban et al. (2008a ▶,b ▶, 2009 ▶); Parthiban, Ramkumar, Kim et al. (2008 ▶); Parthiban, Ramkumar, Santan et al. (2008 ▶); Parthiban, Thirumurugan et al. (2008 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C20H19F2NO

M = 327.36

Triclinic,

a = 7.4699 (3) Å

b = 10.6621 (4) Å

c = 10.7131 (4) Å

α = 78.027 (2)°

β = 78.946 (2)°

γ = 87.201 (2)°

V = 819.16 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.42 × 0.38 × 0.12 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.960, T max = 0.989

11219 measured reflections

3913 independent reflections

2564 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.156

S = 0.81

3913 reflections

221 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus; 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/S1600536809022065/bq2146sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022065/bq2146Isup2.hkl

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

C20H19F2NO	Z = 2
Mr = 327.36	F(000) = 344
Triclinic, P1	Dx = 1.327 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4699 (3) Å	Cell parameters from 3420 reflections
b = 10.6621 (4) Å	θ = 2.5–27.4°
c = 10.7131 (4) Å	µ = 0.10 mm−1
α = 78.027 (2)°	T = 298 K
β = 78.946 (2)°	Block, colourless
γ = 87.201 (2)°	0.42 × 0.38 × 0.12 mm
V = 819.16 (5) Å3

Bruker APEXII CCD area-detector diffractometer	3913 independent reflections
Radiation source: fine-focus sealed tube	2564 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 28.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −9→9
Tmin = 0.960, Tmax = 0.989	k = −14→14
11219 measured reflections	l = −14→14

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) = 0.156	H atoms treated by a mixture of independent and constrained refinement
S = 0.81	w = 1/[σ2(Fo2) + (0.1P)2 + 0.2685P] where P = (Fo2 + 2Fc2)/3
3913 reflections	(Δ/σ)max < 0.001
221 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.20 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 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 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	0.2684 (2)	0.16060 (16)	0.96799 (14)	0.0419 (4)
H1	0.3499	0.0869	0.9585	0.050*
C2	0.3813 (2)	0.27242 (18)	0.98432 (15)	0.0481 (4)
H2	0.4408	0.2431	1.0594	0.058*
C3	0.2715 (3)	0.39499 (18)	1.00204 (17)	0.0546 (5)
H3A	0.1694	0.3730	1.0734	0.066*
H3B	0.3485	0.4532	1.0261	0.066*
C4	0.1990 (3)	0.46430 (18)	0.88289 (19)	0.0595 (5)
H4A	0.1607	0.5502	0.8941	0.071*
H4B	0.0925	0.4196	0.8758	0.071*
C5	0.3381 (3)	0.47348 (18)	0.75758 (18)	0.0591 (5)
H5A	0.4243	0.5403	0.7526	0.071*
H5B	0.2755	0.4987	0.6847	0.071*
C6	0.4445 (2)	0.34774 (19)	0.74473 (16)	0.0506 (4)
H6	0.5433	0.3651	0.6689	0.061*
C7	0.3290 (2)	0.23549 (16)	0.73240 (14)	0.0431 (4)
H7	0.4101	0.1616	0.7234	0.052*
C8	0.5261 (2)	0.3061 (2)	0.86420 (17)	0.0540 (5)
C9	0.1194 (2)	0.12155 (15)	1.08599 (14)	0.0397 (4)
C10	−0.0618 (2)	0.15942 (16)	1.08968 (16)	0.0463 (4)
H10	−0.0971	0.2074	1.0153	0.056*
C11	−0.1906 (3)	0.12692 (19)	1.20224 (18)	0.0560 (5)
H11	−0.3111	0.1535	1.2026	0.067*
C12	−0.1423 (3)	0.05585 (19)	1.31351 (17)	0.0595 (5)
H12	−0.2294	0.0355	1.3891	0.071*
C13	0.0352 (3)	0.01505 (18)	1.31262 (16)	0.0569 (5)
H13	0.0693	−0.0347	1.3866	0.068*
C14	0.1613 (2)	0.04921 (16)	1.20018 (15)	0.0470 (4)
C15	0.2390 (2)	0.26888 (15)	0.61458 (14)	0.0415 (4)
C16	0.3352 (2)	0.25928 (19)	0.49306 (16)	0.0524 (4)
C17	0.2607 (3)	0.2853 (2)	0.38267 (16)	0.0638 (5)
H17	0.3306	0.2767	0.3031	0.077*
C18	0.0817 (3)	0.3240 (2)	0.39162 (17)	0.0641 (5)
H18	0.0289	0.3419	0.3180	0.077*
C19	−0.0185 (3)	0.3362 (2)	0.50969 (18)	0.0586 (5)
H19	−0.1396	0.3630	0.5158	0.070*
C20	0.0587 (2)	0.30888 (17)	0.62043 (15)	0.0483 (4)
H20	−0.0116	0.3176	0.6998	0.058*
F1	0.33764 (16)	0.01112 (12)	1.20093 (11)	0.0726 (4)
F2	0.51212 (16)	0.21980 (16)	0.48284 (11)	0.0853 (4)
N1	0.19010 (18)	0.19950 (13)	0.85064 (11)	0.0397 (3)
O1	0.68765 (18)	0.30314 (19)	0.86537 (14)	0.0831 (5)
H1A	0.129 (3)	0.1358 (19)	0.8399 (17)	0.050 (5)*

	U11	U22	U33	U12	U13	U23
C1	0.0392 (9)	0.0502 (9)	0.0351 (7)	0.0105 (7)	−0.0090 (6)	−0.0071 (6)
C2	0.0358 (9)	0.0718 (12)	0.0383 (8)	−0.0009 (8)	−0.0129 (7)	−0.0095 (7)
C3	0.0525 (11)	0.0631 (11)	0.0508 (9)	−0.0147 (8)	−0.0022 (8)	−0.0209 (8)
C4	0.0605 (12)	0.0489 (10)	0.0693 (12)	0.0008 (8)	−0.0086 (9)	−0.0159 (9)
C5	0.0642 (13)	0.0551 (11)	0.0563 (10)	−0.0146 (9)	−0.0138 (9)	−0.0020 (8)
C6	0.0322 (9)	0.0761 (12)	0.0394 (8)	−0.0063 (8)	−0.0011 (6)	−0.0058 (8)
C7	0.0383 (9)	0.0550 (9)	0.0346 (7)	0.0099 (7)	−0.0049 (6)	−0.0096 (6)
C8	0.0326 (9)	0.0790 (13)	0.0511 (9)	−0.0024 (8)	−0.0082 (7)	−0.0138 (9)
C9	0.0453 (9)	0.0394 (8)	0.0346 (7)	0.0037 (6)	−0.0101 (6)	−0.0068 (6)
C10	0.0446 (10)	0.0486 (9)	0.0438 (8)	0.0023 (7)	−0.0109 (7)	−0.0035 (7)
C11	0.0452 (10)	0.0608 (11)	0.0579 (10)	−0.0033 (8)	−0.0012 (8)	−0.0098 (8)
C12	0.0694 (14)	0.0598 (11)	0.0437 (9)	−0.0146 (10)	0.0050 (8)	−0.0087 (8)
C13	0.0797 (14)	0.0511 (10)	0.0377 (8)	−0.0041 (9)	−0.0130 (8)	−0.0011 (7)
C14	0.0542 (11)	0.0456 (9)	0.0423 (8)	0.0080 (7)	−0.0159 (7)	−0.0064 (7)
C15	0.0440 (9)	0.0463 (9)	0.0330 (7)	−0.0007 (7)	−0.0048 (6)	−0.0073 (6)
C16	0.0469 (10)	0.0682 (12)	0.0413 (8)	−0.0012 (8)	−0.0013 (7)	−0.0152 (8)
C17	0.0727 (14)	0.0846 (14)	0.0337 (8)	−0.0122 (11)	−0.0027 (8)	−0.0149 (8)
C18	0.0746 (14)	0.0775 (14)	0.0419 (9)	−0.0108 (11)	−0.0218 (9)	−0.0032 (9)
C19	0.0521 (11)	0.0728 (13)	0.0504 (10)	0.0027 (9)	−0.0182 (8)	−0.0036 (8)
C20	0.0469 (10)	0.0581 (10)	0.0377 (8)	0.0034 (8)	−0.0067 (7)	−0.0068 (7)
F1	0.0669 (8)	0.0863 (9)	0.0600 (7)	0.0256 (6)	−0.0257 (6)	0.0019 (6)
F2	0.0542 (7)	0.1445 (13)	0.0570 (7)	0.0195 (7)	0.0026 (5)	−0.0363 (7)
N1	0.0402 (8)	0.0478 (8)	0.0312 (6)	−0.0022 (6)	−0.0083 (5)	−0.0062 (5)
O1	0.0315 (8)	0.1455 (16)	0.0696 (9)	−0.0015 (8)	−0.0105 (6)	−0.0143 (9)

C1—N1	1.4617 (19)	C9—C14	1.386 (2)
C1—C9	1.516 (2)	C9—C10	1.389 (2)
C1—C2	1.551 (3)	C10—C11	1.384 (2)
C1—H1	0.9800	C10—H10	0.9300
C2—C8	1.506 (2)	C11—C12	1.374 (3)
C2—C3	1.535 (3)	C11—H11	0.9300
C2—H2	0.9800	C12—C13	1.374 (3)
C3—C4	1.518 (3)	C12—H12	0.9300
C3—H3A	0.9700	C13—C14	1.374 (2)
C3—H3B	0.9700	C13—H13	0.9300
C4—C5	1.520 (3)	C14—F1	1.361 (2)
C4—H4A	0.9700	C15—C16	1.382 (2)
C4—H4B	0.9700	C15—C20	1.386 (2)
C5—C6	1.542 (3)	C16—F2	1.358 (2)
C5—H5A	0.9700	C16—C17	1.373 (3)
C5—H5B	0.9700	C17—C18	1.371 (3)
C6—C8	1.498 (2)	C17—H17	0.9300
C6—C7	1.550 (3)	C18—C19	1.368 (3)
C6—H6	0.9800	C18—H18	0.9300
C7—N1	1.4703 (19)	C19—C20	1.388 (2)
C7—C15	1.513 (2)	C19—H19	0.9300
C7—H7	0.9800	C20—H20	0.9300
C8—O1	1.208 (2)	N1—H1A	0.88 (2)
N1—C1—C9	110.56 (13)	O1—C8—C6	124.57 (16)
N1—C1—C2	109.45 (13)	O1—C8—C2	123.79 (16)
C9—C1—C2	110.71 (13)	C6—C8—C2	111.61 (14)
N1—C1—H1	108.7	C14—C9—C10	116.13 (14)
C9—C1—H1	108.7	C14—C9—C1	120.38 (14)
C2—C1—H1	108.7	C10—C9—C1	123.42 (13)
C8—C2—C3	107.64 (15)	C11—C10—C9	121.07 (15)
C8—C2—C1	107.86 (14)	C11—C10—H10	119.5
C3—C2—C1	114.94 (14)	C9—C10—H10	119.5
C8—C2—H2	108.8	C12—C11—C10	120.71 (18)
C3—C2—H2	108.8	C12—C11—H11	119.6
C1—C2—H2	108.8	C10—C11—H11	119.6
C4—C3—C2	114.55 (14)	C13—C12—C11	119.71 (16)
C4—C3—H3A	108.6	C13—C12—H12	120.1
C2—C3—H3A	108.6	C11—C12—H12	120.1
C4—C3—H3B	108.6	C14—C13—C12	118.66 (16)
C2—C3—H3B	108.6	C14—C13—H13	120.7
H3A—C3—H3B	107.6	C12—C13—H13	120.7
C3—C4—C5	113.26 (16)	F1—C14—C13	118.33 (15)
C3—C4—H4A	108.9	F1—C14—C9	117.96 (15)
C5—C4—H4A	108.9	C13—C14—C9	123.70 (16)
C3—C4—H4B	108.9	C16—C15—C20	116.11 (15)
C5—C4—H4B	108.9	C16—C15—C7	120.57 (15)
H4A—C4—H4B	107.7	C20—C15—C7	123.31 (13)
C4—C5—C6	114.00 (15)	F2—C16—C17	118.29 (15)
C4—C5—H5A	108.8	F2—C16—C15	118.14 (15)
C6—C5—H5A	108.8	C17—C16—C15	123.57 (17)
C4—C5—H5B	108.8	C18—C17—C16	118.98 (16)
C6—C5—H5B	108.8	C18—C17—H17	120.5
H5A—C5—H5B	107.6	C16—C17—H17	120.5
C8—C6—C5	107.17 (15)	C19—C18—C17	119.53 (17)
C8—C6—C7	107.89 (15)	C19—C18—H18	120.2
C5—C6—C7	115.27 (14)	C17—C18—H18	120.2
C8—C6—H6	108.8	C18—C19—C20	120.73 (18)
C5—C6—H6	108.8	C18—C19—H19	119.6
C7—C6—H6	108.8	C20—C19—H19	119.6
N1—C7—C15	110.02 (13)	C15—C20—C19	121.07 (15)
N1—C7—C6	109.92 (13)	C15—C20—H20	119.5
C15—C7—C6	111.89 (13)	C19—C20—H20	119.5
N1—C7—H7	108.3	C1—N1—C7	112.94 (12)
C15—C7—H7	108.3	C1—N1—H1A	109.7 (12)
C6—C7—H7	108.3	C7—N1—H1A	106.9 (12)
N1—C1—C2—C8	−57.90 (16)	C9—C10—C11—C12	−0.1 (3)
C9—C1—C2—C8	179.98 (13)	C10—C11—C12—C13	−0.9 (3)
N1—C1—C2—C3	62.16 (17)	C11—C12—C13—C14	1.4 (3)
C9—C1—C2—C3	−59.96 (17)	C12—C13—C14—F1	178.41 (16)
C8—C2—C3—C4	52.2 (2)	C12—C13—C14—C9	−0.9 (3)
C1—C2—C3—C4	−68.03 (19)	C10—C9—C14—F1	−179.44 (15)
C2—C3—C4—C5	−43.7 (2)	C1—C9—C14—F1	−2.3 (2)
C3—C4—C5—C6	44.4 (2)	C10—C9—C14—C13	−0.1 (3)
C4—C5—C6—C8	−53.8 (2)	C1—C9—C14—C13	177.01 (16)
C4—C5—C6—C7	66.3 (2)	N1—C7—C15—C16	−155.80 (16)
C8—C6—C7—N1	56.93 (17)	C6—C7—C15—C16	81.71 (19)
C5—C6—C7—N1	−62.77 (17)	N1—C7—C15—C20	23.5 (2)
C8—C6—C7—C15	179.48 (13)	C6—C7—C15—C20	−98.96 (18)
C5—C6—C7—C15	59.78 (17)	C20—C15—C16—F2	−179.68 (16)
C5—C6—C8—O1	−113.1 (2)	C7—C15—C16—F2	−0.3 (3)
C7—C6—C8—O1	122.2 (2)	C20—C15—C16—C17	−0.9 (3)
C5—C6—C8—C2	64.94 (19)	C7—C15—C16—C17	178.47 (18)
C7—C6—C8—C2	−59.75 (19)	F2—C16—C17—C18	179.38 (18)
C3—C2—C8—O1	113.9 (2)	C15—C16—C17—C18	0.6 (3)
C1—C2—C8—O1	−121.6 (2)	C16—C17—C18—C19	0.1 (3)
C3—C2—C8—C6	−64.20 (19)	C17—C18—C19—C20	−0.4 (3)
C1—C2—C8—C6	60.36 (19)	C16—C15—C20—C19	0.5 (3)
N1—C1—C9—C14	162.27 (15)	C7—C15—C20—C19	−178.81 (17)
C2—C1—C9—C14	−76.27 (19)	C18—C19—C20—C15	0.1 (3)
N1—C1—C9—C10	−20.8 (2)	C9—C1—N1—C7	−178.60 (13)
C2—C1—C9—C10	100.64 (18)	C2—C1—N1—C7	59.20 (17)
C14—C9—C10—C11	0.6 (2)	C15—C7—N1—C1	177.51 (13)
C1—C9—C10—C11	−176.38 (16)	C6—C7—N1—C1	−58.84 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cgi	0.90 (4)	2.72 (2)	3.58 (16)	167.3 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cgi	0.90 (4)	2.72 (2)	3.58 (16)	167.3 (19)

Symmetry code: (i) . Cg is the centroid of C9–C14 phenyl ring.