1,1'-(4,4'-Bipiperidine-1,1'-di-yl)bis-(2,2,2-trifluoro-ethanone).

The title compound, C(14)H(18)F(6)N(2)O(2), has a central center of symmetry with both piperidine rings occurring in regular chair conformations. Even though the structure is fairly compact with no sizable voids, the shortest H⋯O distance is as long as 2.58 Å.

Related literature

For applications of and structures related to 4,4′-bipiperidine compounds, see: Medina et al. (1991 ▶); Li et al. (2009 ▶); Wang et al. (2007 ▶); Melchiorre et al. (2001 ▶); Adams et al. (2006 ▶); Angeloni & Orpen (2001 ▶); De las Casas Engel et al. (2010 ▶). For a related synthesis, see: Schenck et al. (2004 ▶). For inter­pretation of C—H⋯F bond configurations, see: Shimoni & Glusker (1994 ▶). For the use of a large specimen for data collection, see: Görbitz (1999 ▶).

Experimental

Crystal data

C14H18F6N2O2

M = 360.30

Triclinic,

a = 6.6825 (12) Å

b = 6.7350 (12) Å

c = 9.3089 (16) Å

α = 99.952 (2)°

β = 108.564 (2)°

γ = 101.542 (2)°

V = 376.30 (12) Å3

Z = 1

Mo Kα radiation

μ = 0.16 mm−1

T = 105 K

1.00 × 0.50 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.921, T max = 0.962

3303 measured reflections

1731 independent reflections

1586 reflections with I > 2σ(I)

R int = 0.009

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.080

S = 1.06

1731 reflections

109 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT-Plus (Bruker, 2007 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811022434/ng5179sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811022434/ng5179Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811022434/ng5179Isup3.cml

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

C14H18F6N2O2	Z = 1
Mr = 360.30	F(000) = 186
Triclinic, P1	Dx = 1.590 Mg m−3
Hall symbol: -P 1	Melting point: 397 K
a = 6.6825 (12) Å	Mo Kα radiation, λ = 0.71073 Å
b = 6.7350 (12) Å	Cell parameters from 2545 reflections
c = 9.3089 (16) Å	θ = 2.4–28.3°
α = 99.952 (2)°	µ = 0.16 mm−1
β = 108.564 (2)°	T = 105 K
γ = 101.542 (2)°	Rods, colourless
V = 376.30 (12) Å3	1.00 × 0.50 × 0.25 mm

Bruker APEXII CCD diffractometer	1731 independent reflections
Radiation source: fine-focus sealed tube	1586 reflections with I > 2σ(I)
graphite	Rint = 0.009
Detector resolution: 8.3 pixels mm-1	θmax = 28.6°, θmin = 2.4°
Sets of exposures each taken over 0.5° ω rotation scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2007)	k = −8→8
Tmin = 0.921, Tmax = 0.962	l = −12→12
3303 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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0398P)2 + 0.1258P] where P = (Fo2 + 2Fc2)/3
1731 reflections	(Δ/σ)max = 0.008
109 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.23 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
F1	0.11060 (12)	0.31663 (10)	0.84127 (9)	0.03113 (19)
F2	0.00855 (11)	0.51373 (11)	0.68885 (8)	0.02834 (18)
F3	0.13374 (10)	0.63747 (10)	0.93992 (7)	0.02236 (16)
O1	0.49112 (14)	0.43556 (12)	0.82275 (10)	0.02475 (19)
N1	0.47091 (14)	0.76768 (13)	0.81595 (10)	0.01700 (19)
C2	0.68525 (17)	0.82626 (17)	0.80093 (12)	0.0199 (2)
H21	0.7640	0.7193	0.8255	0.024*
H22	0.7745	0.9622	0.8764	0.024*
C3	0.65544 (17)	0.84357 (16)	0.63442 (12)	0.0186 (2)
H31	0.5798	0.7036	0.5607	0.022*
H32	0.8014	0.8906	0.6274	0.022*
C4	0.52192 (16)	0.99793 (15)	0.58605 (11)	0.0155 (2)
H41	0.6099	1.1413	0.6534	0.019*
C5	0.30751 (16)	0.94359 (15)	0.61687 (11)	0.0166 (2)
H51	0.2321	1.0545	0.5987	0.020*
H52	0.2099	0.8101	0.5418	0.020*
C6	0.34705 (17)	0.92258 (15)	0.78370 (12)	0.0171 (2)
H61	0.4304	1.0600	0.8592	0.021*
H62	0.2047	0.8779	0.7965	0.021*
C7	0.39316 (17)	0.57031 (16)	0.82058 (11)	0.0176 (2)
C8	0.15978 (18)	0.51030 (16)	0.82412 (13)	0.0210 (2)

	U11	U22	U33	U12	U13	U23
F1	0.0357 (4)	0.0179 (3)	0.0457 (4)	0.0046 (3)	0.0226 (3)	0.0114 (3)
F2	0.0223 (3)	0.0307 (4)	0.0252 (3)	0.0026 (3)	0.0040 (3)	0.0043 (3)
F3	0.0247 (3)	0.0240 (3)	0.0250 (3)	0.0098 (3)	0.0148 (3)	0.0082 (3)
O1	0.0318 (4)	0.0201 (4)	0.0305 (4)	0.0140 (3)	0.0164 (4)	0.0093 (3)
N1	0.0180 (4)	0.0177 (4)	0.0194 (4)	0.0078 (3)	0.0087 (3)	0.0080 (3)
C2	0.0169 (5)	0.0246 (5)	0.0218 (5)	0.0080 (4)	0.0078 (4)	0.0110 (4)
C3	0.0184 (5)	0.0217 (5)	0.0207 (5)	0.0093 (4)	0.0093 (4)	0.0095 (4)
C4	0.0164 (4)	0.0152 (4)	0.0163 (5)	0.0055 (4)	0.0065 (4)	0.0052 (4)
C5	0.0175 (5)	0.0175 (4)	0.0174 (5)	0.0073 (4)	0.0072 (4)	0.0063 (4)
C6	0.0211 (5)	0.0160 (4)	0.0185 (5)	0.0090 (4)	0.0093 (4)	0.0065 (4)
C7	0.0218 (5)	0.0174 (5)	0.0157 (4)	0.0070 (4)	0.0086 (4)	0.0043 (4)
C8	0.0238 (5)	0.0171 (5)	0.0233 (5)	0.0053 (4)	0.0103 (4)	0.0058 (4)

F1—C8	1.3299 (12)	C3—H31	0.9900
F2—C8	1.3478 (13)	C3—H32	0.9900
F3—C8	1.3363 (12)	C4—C5	1.5354 (14)
O1—C7	1.2199 (13)	C4—C4i	1.5404 (19)
N1—C7	1.3403 (13)	C4—H41	1.0000
N1—C2	1.4654 (13)	C5—C6	1.5268 (13)
N1—C6	1.4694 (12)	C5—H51	0.9900
C2—C3	1.5267 (14)	C5—H52	0.9900
C2—H21	0.9900	C6—H61	0.9900
C2—H22	0.9900	C6—H62	0.9900
C3—C4	1.5352 (13)	C7—C8	1.5433 (15)
C7—N1—C2	118.28 (8)	C6—C5—C4	112.24 (8)
C7—N1—C6	127.41 (9)	C6—C5—H51	109.2
C2—N1—C6	112.38 (8)	C4—C5—H51	109.2
N1—C2—C3	110.03 (8)	C6—C5—H52	109.2
N1—C2—H21	109.7	C4—C5—H52	109.2
C3—C2—H21	109.7	H51—C5—H52	107.9
N1—C2—H22	109.7	N1—C6—C5	109.91 (8)
C3—C2—H22	109.7	N1—C6—H61	109.7
H21—C2—H22	108.2	C5—C6—H61	109.7
C2—C3—C4	111.99 (8)	N1—C6—H62	109.7
C2—C3—H31	109.2	C5—C6—H62	109.7
C4—C3—H31	109.2	H61—C6—H62	108.2
C2—C3—H32	109.2	O1—C7—N1	125.64 (10)
C4—C3—H32	109.2	O1—C7—C8	117.66 (9)
H31—C3—H32	107.9	N1—C7—C8	116.70 (9)
C5—C4—C3	109.77 (8)	F1—C8—F3	107.55 (8)
C5—C4—C4i	111.59 (10)	F1—C8—F2	107.07 (9)
C3—C4—C4i	111.60 (10)	F3—C8—F2	107.07 (9)
C5—C4—H41	107.9	F1—C8—C7	110.32 (9)
C3—C4—H41	107.9	F3—C8—C7	113.47 (9)
C4i—C4—H41	107.9	F2—C8—C7	111.08 (8)
C7—N1—C2—C3	104.98 (10)	C2—N1—C7—O1	4.65 (15)
C6—N1—C2—C3	−60.38 (11)	C6—N1—C7—O1	167.54 (10)
N1—C2—C3—C4	55.87 (11)	C2—N1—C7—C8	−175.62 (8)
C2—C3—C4—C5	−51.51 (11)	C6—N1—C7—C8	−12.72 (15)
C2—C3—C4—C4i	−175.77 (10)	O1—C7—C8—F1	4.75 (13)
C3—C4—C5—C6	51.41 (11)	N1—C7—C8—F1	−175.01 (8)
C4i—C4—C5—C6	175.67 (9)	O1—C7—C8—F3	125.51 (10)
C7—N1—C6—C5	−103.67 (11)	N1—C7—C8—F3	−54.25 (12)
C2—N1—C6—C5	60.06 (11)	O1—C7—C8—F2	−113.81 (10)
C4—C5—C6—N1	−55.39 (11)	N1—C7—C8—F2	66.43 (12)