11-{[2-(3-Fluoro-phen-yl)eth-yl](meth-yl)amino}-penta-cyclo-[5.4.0.0.0.0]undecan-8-one.

In the title compound, C(20)H(22)FNO, the distances close to the carbonyl and amine are: N-O = 3.232 (4) Å and N-C = 2.666 (5) Å. The crystal packing is unremarkable.

Related literature

For in vitro σ-receptor affinity of tris­homocubane derivatives related to the title compound, see: Nguyen et al. (1996 ▶); Liu et al. (1999 ▶). For in vivo pharmacology of related tris­homocubanes, see: Liu et al. (2001 ▶, 2007 ▶). For rationalization of observed structure–affinity relationships of tris­homocubanes at σ-receptors using mol­ecular modeling, see: Banister et al. (2010 ▶). For X-ray crystallographic studies of biologically active tris­homocubanes related to the title compound, see: Hambley et al. (2000 ▶).

Experimental

Crystal data

C20H22FNO

M = 311.39

Monoclinic,

a = 10.5450 (18) Å

b = 10.980 (2) Å

c = 13.822 (3) Å

β = 95.214 (8)°

V = 1593.8 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 150 K

0.25 × 0.20 × 0.15 mm

Data collection

Bruker–Nonius APEXII FR591 diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ▶) T min = 0.684, T max = 0.746

17270 measured reflections

2773 independent reflections

1566 reflections with I > 2σ(I)

R int = 0.087

Refinement

R[F 2 > 2σ(F 2)] = 0.087

wR(F 2) = 0.271

S = 1.14

2773 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.69 e Å−3

Δρmin = −0.48 e Å−3

Data collection: APEX2 (Bruker–Nonius, 2003 ▶); cell refinement: SAINT (Bruker–Nonius, 2003); data reduction: SAINT and XPREP (Bruker–Nonius, 2003 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶), WinGX (Farrugia, 1999 ▶) and POV-RAY (Cason, 2002 ▶); software used to prepare material for publication: enCIFer (Allen et al., 2004 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810038523/rk2233sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038523/rk2233Isup2.hkl

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

C20H22FNO	F(000) = 664
Mr = 311.39	Dx = 1.298 Mg m−3
Monoclinic, P21/n	Melting point: 363.5 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 10.5450 (18) Å	Cell parameters from 2297 reflections
b = 10.980 (2) Å	θ = 2.7–23.1°
c = 13.822 (3) Å	µ = 0.09 mm−1
β = 95.214 (8)°	T = 150 K
V = 1593.8 (5) Å3	Block, colourless
Z = 4	0.25 × 0.20 × 0.15 mm

Bruker–Nonius APEXII FR591 diffractometer	2773 independent reflections
Radiation source: rotating anode	1566 reflections with I > 2σ(I)
graphite	Rint = 0.087
ω and φ scans	θmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	h = −12→12
Tmin = 0.684, Tmax = 0.746	k = −13→12
17270 measured reflections	l = −16→16

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)] = 0.087	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.271	H-atom parameters constrained
S = 1.14	w = 1/[σ2(Fo2) + (0.1415P)2 + 0.2766P] where P = (Fo2 + 2Fc2)/3
2773 reflections	(Δ/σ)max < 0.001
209 parameters	Δρmax = 0.69 e Å−3
0 restraints	Δρmin = −0.47 e Å−3

Experimental. The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 150 K under a cold nitrogen gas stream supplied by an Oxford Cryosystems Cryostream and data were collected at this temperature.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.5938 (5)	0.3609 (4)	0.6172 (5)	0.0588 (17)
C2	0.5803 (4)	0.2626 (4)	0.6825 (3)	0.0399 (11)
H2	0.5450	0.2744	0.7426	0.048*
C3	0.6209 (3)	0.1482 (3)	0.6545 (3)	0.0250 (9)
C4	0.6703 (4)	0.1374 (4)	0.5656 (3)	0.0382 (11)
H4	0.6988	0.0598	0.5462	0.046*
C5	0.6797 (5)	0.2343 (6)	0.5047 (4)	0.0609 (16)
H5	0.7123	0.2220	0.4436	0.073*
C6	0.6442 (6)	0.3449 (6)	0.5291 (5)	0.0680 (18)
H6	0.6532	0.4120	0.4869	0.082*
C7	0.6123 (5)	0.0379 (4)	0.7189 (3)	0.0503 (13)
H7A	0.6156	0.0645	0.7875	0.060*
H7B	0.6865	−0.0156	0.7121	0.060*
C8	0.4885 (4)	−0.0351 (4)	0.6931 (3)	0.0304 (10)
H8A	0.4162	0.0131	0.7137	0.036*
H8B	0.4758	−0.0436	0.6216	0.036*
C9	0.5715 (4)	−0.2420 (4)	0.6958 (4)	0.0490 (13)
H9A	0.6587	−0.2249	0.7233	0.074*
H9B	0.5661	−0.2326	0.6250	0.074*
H9C	0.5486	−0.3256	0.7119	0.074*
C10	0.4948 (4)	−0.1550 (4)	0.8423 (3)	0.0348 (11)
H10	0.5795	−0.1212	0.8675	0.042*
C11	0.3871 (4)	−0.0811 (4)	0.8822 (3)	0.0408 (12)
H11	0.3956	0.0094	0.8774	0.049*
C12	0.3700 (5)	−0.1303 (4)	0.9854 (4)	0.0506 (13)
H12	0.3736	−0.0702	1.0400	0.061*
C13	0.4537 (4)	−0.2406 (5)	0.9980 (3)	0.0502 (14)
H13	0.5343	−0.2286	1.0409	0.060*
C14	0.4724 (4)	−0.2781 (4)	0.8898 (3)	0.0479 (13)
H14	0.5445	−0.3364	0.8851	0.057*
C15	0.3636 (5)	−0.3402 (5)	1.0322 (4)	0.0542 (14)
H15A	0.4011	−0.4229	1.0328	0.065*
H15B	0.3314	−0.3216	1.0957	0.065*
C16	0.2635 (4)	−0.3182 (5)	0.9450 (3)	0.0470 (13)
H16	0.1859	−0.3705	0.9451	0.056*
C17	0.3392 (4)	−0.3332 (4)	0.8509 (4)	0.0469 (13)
H17	0.3429	−0.4186	0.8262	0.056*
C18	0.2639 (4)	−0.2484 (4)	0.7847 (3)	0.0379 (11)
C19	0.2540 (4)	−0.1331 (5)	0.8456 (3)	0.0429 (12)
H19	0.1893	−0.0720	0.8196	0.052*
C20	0.2372 (4)	−0.1834 (4)	0.9485 (3)	0.0435 (12)
H20	0.1614	−0.1557	0.9812	0.052*
N1	0.4837 (3)	−0.1570 (3)	0.7364 (2)	0.0259 (8)
O1	0.2010 (3)	−0.2730 (3)	0.70829 (19)	0.0431 (9)
F1	0.5547 (4)	0.4710 (3)	0.6455 (4)	0.128 (2)

	U11	U22	U33	U12	U13	U23
C1	0.035 (3)	0.016 (2)	0.119 (5)	0.004 (2)	−0.030 (3)	−0.007 (3)
C2	0.023 (2)	0.053 (3)	0.043 (3)	−0.007 (2)	−0.0052 (18)	−0.016 (2)
C3	0.028 (2)	0.026 (2)	0.020 (2)	−0.0055 (18)	−0.0039 (16)	0.0031 (16)
C4	0.036 (2)	0.045 (3)	0.033 (3)	0.001 (2)	0.0019 (19)	−0.007 (2)
C5	0.044 (3)	0.104 (5)	0.034 (3)	−0.023 (3)	−0.001 (2)	0.017 (3)
C6	0.056 (4)	0.070 (4)	0.074 (4)	−0.032 (3)	−0.019 (3)	0.038 (4)
C7	0.053 (3)	0.047 (3)	0.046 (3)	−0.028 (2)	−0.021 (2)	0.021 (2)
C8	0.028 (2)	0.036 (2)	0.026 (2)	−0.0048 (19)	−0.0042 (17)	0.0024 (18)
C9	0.039 (3)	0.044 (3)	0.063 (3)	0.007 (2)	0.001 (2)	−0.011 (2)
C10	0.031 (2)	0.041 (3)	0.030 (2)	−0.017 (2)	−0.0098 (18)	0.0099 (19)
C11	0.046 (3)	0.050 (3)	0.027 (2)	−0.023 (2)	0.009 (2)	−0.006 (2)
C12	0.066 (3)	0.043 (3)	0.040 (3)	−0.015 (3)	−0.009 (2)	−0.005 (2)
C13	0.031 (2)	0.090 (4)	0.028 (2)	−0.011 (3)	−0.0097 (19)	0.012 (2)
C14	0.040 (3)	0.044 (3)	0.056 (3)	−0.014 (2)	−0.015 (2)	0.020 (2)
C15	0.057 (3)	0.059 (3)	0.045 (3)	−0.008 (3)	−0.006 (2)	0.018 (2)
C16	0.046 (3)	0.070 (4)	0.023 (2)	−0.028 (3)	−0.003 (2)	0.006 (2)
C17	0.042 (3)	0.037 (3)	0.058 (3)	−0.016 (2)	−0.013 (2)	0.010 (2)
C18	0.033 (2)	0.051 (3)	0.028 (2)	−0.019 (2)	−0.0031 (19)	0.008 (2)
C19	0.039 (3)	0.058 (3)	0.033 (3)	−0.006 (2)	0.005 (2)	0.001 (2)
C20	0.039 (3)	0.060 (3)	0.032 (3)	−0.002 (2)	0.006 (2)	0.008 (2)
N1	0.0248 (17)	0.0248 (18)	0.0278 (19)	−0.0006 (15)	0.0002 (13)	0.0012 (14)
O1	0.0350 (16)	0.070 (2)	0.0232 (16)	−0.0208 (16)	−0.0058 (13)	0.0024 (14)
F1	0.088 (3)	0.038 (2)	0.246 (6)	0.0133 (19)	−0.048 (3)	−0.037 (2)

C1—F1	1.347 (6)	C10—H10	1.0000
C1—C6	1.384 (9)	C11—C12	1.551 (7)
C1—C2	1.422 (7)	C11—C19	1.557 (6)
C2—C3	1.393 (6)	C11—H11	1.0000
C2—H2	0.9500	C12—C13	1.499 (7)
C3—C4	1.382 (6)	C12—C20	1.560 (7)
C3—C7	1.511 (6)	C12—H12	1.0000
C4—C5	1.366 (7)	C13—C15	1.551 (7)
C4—H4	0.9500	C13—C14	1.581 (7)
C5—C6	1.323 (8)	C13—H13	1.0000
C5—H5	0.9500	C14—C17	1.579 (6)
C6—H6	0.9500	C14—H14	1.0000
C7—C8	1.546 (6)	C15—C16	1.546 (6)
C7—H7A	0.9900	C15—H15A	0.9900
C7—H7B	0.9900	C15—H15B	0.9900
C8—N1	1.469 (5)	C16—C20	1.508 (7)
C8—H8A	0.9900	C16—C17	1.595 (7)
C8—H8B	0.9900	C16—H16	1.0000
C9—N1	1.463 (5)	C17—C18	1.484 (6)
C9—H9A	0.9800	C17—H17	1.0000
C9—H9B	0.9800	C18—O1	1.225 (5)
C9—H9C	0.9800	C18—C19	1.529 (7)
C10—N1	1.458 (5)	C19—C20	1.550 (6)
C10—C14	1.531 (6)	C19—H19	1.0000
C10—C11	1.538 (6)	C20—H20	1.0000
F1—C1—C6	121.4 (6)	C13—C12—H12	117.7
F1—C1—C2	116.5 (6)	C11—C12—H12	117.7
C6—C1—C2	122.0 (5)	C20—C12—H12	117.7
C3—C2—C1	117.2 (4)	C12—C13—C15	103.6 (4)
C3—C2—H2	121.4	C12—C13—C14	102.9 (3)
C1—C2—H2	121.4	C15—C13—C14	103.7 (4)
C4—C3—C2	118.3 (4)	C12—C13—H13	115.0
C4—C3—C7	120.2 (4)	C15—C13—H13	115.0
C2—C3—C7	121.5 (4)	C14—C13—H13	115.0
C5—C4—C3	122.4 (5)	C10—C14—C17	111.0 (3)
C5—C4—H4	118.8	C10—C14—C13	102.3 (4)
C3—C4—H4	118.8	C17—C14—C13	103.8 (4)
C6—C5—C4	121.3 (5)	C10—C14—H14	113.0
C6—C5—H5	119.3	C17—C14—H14	113.0
C4—C5—H5	119.3	C13—C14—H14	113.0
C5—C6—C1	118.7 (5)	C16—C15—C13	92.6 (3)
C5—C6—H6	120.6	C16—C15—H15A	113.2
C1—C6—H6	120.6	C13—C15—H15A	113.2
C3—C7—C8	112.0 (3)	C16—C15—H15B	113.2
C3—C7—H7A	109.2	C13—C15—H15B	113.2
C8—C7—H7A	109.2	H15A—C15—H15B	110.5
C3—C7—H7B	109.2	C20—C16—C15	104.1 (4)
C8—C7—H7B	109.2	C20—C16—C17	103.6 (4)
H7A—C7—H7B	107.9	C15—C16—C17	105.2 (4)
N1—C8—C7	116.0 (3)	C20—C16—H16	114.2
N1—C8—H8A	108.3	C15—C16—H16	114.2
C7—C8—H8A	108.3	C17—C16—H16	114.2
N1—C8—H8B	108.3	C18—C17—C14	112.3 (3)
C7—C8—H8B	108.3	C18—C17—C16	99.1 (4)
H8A—C8—H8B	107.4	C14—C17—C16	100.2 (4)
N1—C9—H9A	109.5	C18—C17—H17	114.4
N1—C9—H9B	109.5	C14—C17—H17	114.4
H9A—C9—H9B	109.5	C16—C17—H17	114.4
N1—C9—H9C	109.5	O1—C18—C17	127.6 (4)
H9A—C9—H9C	109.5	O1—C18—C19	126.7 (4)
H9B—C9—H9C	109.5	C17—C18—C19	103.9 (4)
N1—C10—C14	114.6 (3)	C18—C19—C20	103.2 (4)
N1—C10—C11	112.0 (3)	C18—C19—C11	112.2 (4)
C14—C10—C11	99.4 (3)	C20—C19—C11	90.4 (3)
N1—C10—H10	110.1	C18—C19—H19	115.9
C14—C10—H10	110.1	C20—C19—H19	115.9
C11—C10—H10	110.1	C11—C19—H19	115.9
C10—C11—C12	107.3 (4)	C16—C20—C19	106.5 (4)
C10—C11—C19	111.3 (3)	C16—C20—C12	102.4 (4)
C12—C11—C19	89.7 (3)	C19—C20—C12	89.6 (3)
C10—C11—H11	115.2	C16—C20—H20	118.0
C12—C11—H11	115.2	C19—C20—H20	118.0
C19—C11—H11	115.2	C12—C20—H20	118.0
C13—C12—C11	105.8 (4)	C10—N1—C9	113.5 (3)
C13—C12—C20	103.8 (4)	C10—N1—C8	113.1 (3)
C11—C12—C20	90.3 (3)	C9—N1—C8	112.3 (3)
F1—C1—C2—C3	−179.7 (4)	C13—C14—C17—C18	104.4 (4)
C6—C1—C2—C3	0.5 (6)	C10—C14—C17—C16	−109.2 (4)
C1—C2—C3—C4	−0.6 (6)	C13—C14—C17—C16	0.0 (4)
C1—C2—C3—C7	179.2 (4)	C20—C16—C17—C18	−41.0 (4)
C2—C3—C4—C5	−0.4 (6)	C15—C16—C17—C18	−150.0 (4)
C7—C3—C4—C5	179.8 (4)	C20—C16—C17—C14	73.7 (4)
C3—C4—C5—C6	1.6 (7)	C15—C16—C17—C14	−35.3 (5)
C4—C5—C6—C1	−1.6 (8)	C14—C17—C18—O1	137.7 (5)
F1—C1—C6—C5	−179.2 (5)	C16—C17—C18—O1	−117.2 (5)
C2—C1—C6—C5	0.6 (8)	C14—C17—C18—C19	−56.7 (5)
C4—C3—C7—C8	−85.8 (5)	C16—C17—C18—C19	48.4 (4)
C2—C3—C7—C8	94.4 (5)	O1—C18—C19—C20	127.7 (4)
C3—C7—C8—N1	167.1 (4)	C17—C18—C19—C20	−38.0 (4)
N1—C10—C11—C12	154.8 (3)	O1—C18—C19—C11	−136.4 (4)
C14—C10—C11—C12	33.3 (4)	C17—C18—C19—C11	58.0 (4)
N1—C10—C11—C19	58.2 (4)	C10—C11—C19—C18	3.5 (5)
C14—C10—C11—C19	−63.3 (4)	C12—C11—C19—C18	−105.0 (4)
C10—C11—C12—C13	−7.4 (5)	C10—C11—C19—C20	108.1 (4)
C19—C11—C12—C13	104.9 (4)	C12—C11—C19—C20	−0.5 (4)
C10—C11—C12—C20	−111.8 (4)	C15—C16—C20—C19	128.1 (4)
C19—C11—C12—C20	0.5 (4)	C17—C16—C20—C19	18.3 (4)
C11—C12—C13—C15	−128.9 (4)	C15—C16—C20—C12	34.8 (4)
C20—C12—C13—C15	−34.7 (4)	C17—C16—C20—C12	−75.0 (4)
C11—C12—C13—C14	−21.1 (4)	C18—C19—C20—C16	10.6 (4)
C20—C12—C13—C14	73.1 (4)	C11—C19—C20—C16	−102.3 (4)
N1—C10—C14—C17	−55.1 (5)	C18—C19—C20—C12	113.4 (4)
C11—C10—C14—C17	64.4 (5)	C11—C19—C20—C12	0.5 (4)
N1—C10—C14—C13	−165.3 (3)	C13—C12—C20—C16	0.0 (4)
C11—C10—C14—C13	−45.8 (4)	C11—C12—C20—C16	106.3 (4)
C12—C13—C14—C10	42.8 (4)	C13—C12—C20—C19	−106.8 (4)
C15—C13—C14—C10	150.5 (4)	C11—C12—C20—C19	−0.5 (4)
C12—C13—C14—C17	−72.8 (4)	C14—C10—N1—C9	−58.3 (5)
C15—C13—C14—C17	34.9 (5)	C11—C10—N1—C9	−170.6 (3)
C12—C13—C15—C16	53.3 (4)	C14—C10—N1—C8	172.2 (3)
C14—C13—C15—C16	−53.9 (4)	C11—C10—N1—C8	59.9 (4)
C13—C15—C16—C20	−53.6 (4)	C7—C8—N1—C10	61.1 (5)
C13—C15—C16—C17	55.0 (4)	C7—C8—N1—C9	−69.0 (5)
C10—C14—C17—C18	−4.9 (6)