5,5'-Bis[(2,2,2-trifluoro-eth-oxy)meth-yl]-2,2'-bipyridine.

The complete molecule of the title compound, C(16)H(14)F(6)N(2)O(2), is generated by crystallographic inversion symmetry, which results in two short intramolecular C-H⋯N hydrogen-bond contacts per molecule. In the crystal, aromatic π-π stacking [centroid-centroid distance = 3.457 (2) Å] and weak C-H⋯π inter-actions occur. A short H⋯H [2.32 (3) Å] contact is present.

Related literature

For related structures and background to the anti-planar geometry of bpy, see: Lu, Tu, Wu et al. (2010 ▶); Iyer et al. (2005 ▶); Heirtzler et al. (2002 ▶); Maury et al. (2001 ▶); Vogtle et al. (1990 ▶). For background to the bipyridine (bpy) ligand, see: Bain et al. (1989 ▶); Chambron & Sauvage (1986 ▶, 1987 ▶); Grätzel (2001 ▶); Haga et al. (2000 ▶); Lu, Tu, Hou et al. (2010 ▶); Lu, Tu, Wen et al. (2010 ▶); Lu et al. (2007 ▶). For C—H⋯H—C inter­actions, see: Wolstenholme & Cameron (2006 ▶).

Experimental

Crystal data

C16H14F6N2O2

M = 380.29

Triclinic,

a = 4.6573 (2) Å

b = 5.6842 (3) Å

c = 15.7273 (8) Å

α = 94.298 (3)°

β = 98.473 (3)°

γ = 105.689 (4)°

V = 393.57 (3) Å3

Z = 1

Mo Kα radiation

μ = 0.15 mm−1

T = 100 K

0.2 × 0.14 × 0.12 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.664, T max = 0.746

6627 measured reflections

1577 independent reflections

1348 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.104

S = 1.12

1577 reflections

146 parameters

All H-atom parameters refined

Δρmax = 0.29 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811000730/fk2030sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000730/fk2030Isup2.hkl

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

C16H14F6N2O2	Z = 1
Mr = 380.29	F(000) = 194
Triclinic, P1	Dx = 1.605 Mg m−3Dm = 1.53 Mg m−3Dm measured by w/v
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.6573 (2) Å	Cell parameters from 3201 reflections
b = 5.6842 (3) Å	θ = 2.6–27.1°
c = 15.7273 (8) Å	µ = 0.15 mm−1
α = 94.298 (3)°	T = 100 K
β = 98.473 (3)°	Prism, colourless
γ = 105.689 (4)°	0.2 × 0.14 × 0.12 mm
V = 393.57 (3) Å3

Bruker APEXII CCD area-detector diffractometer	1348 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 26.4°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −5→5
Tmin = 0.664, Tmax = 0.746	k = −7→7
6627 measured reflections	l = −19→19
1577 independent 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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	All H-atom parameters refined
S = 1.12	w = 1/[σ2(Fo2) + (0.0595P)2 + 0.094P] where P = (Fo2 + 2Fc2)/3
1577 reflections	(Δ/σ)max < 0.001
146 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	1.8989 (2)	1.22574 (16)	0.98212 (6)	0.0271 (3)
F2	1.8270 (2)	1.35589 (16)	0.85765 (6)	0.0299 (3)
F3	1.4537 (2)	1.23169 (17)	0.92410 (6)	0.0294 (3)
O	1.4170 (2)	0.88799 (19)	0.79273 (7)	0.0225 (3)
N	0.6609 (3)	0.3432 (2)	0.58189 (8)	0.0173 (3)
C1	1.1096 (3)	0.6201 (3)	0.67039 (9)	0.0160 (3)
C2	0.8935 (3)	0.3918 (3)	0.64727 (10)	0.0174 (3)
C3	0.6289 (3)	0.5286 (2)	0.53652 (8)	0.0144 (3)
C4	0.8268 (3)	0.7658 (3)	0.55708 (10)	0.0181 (3)
C5	1.0718 (3)	0.8098 (3)	0.62300 (10)	0.0189 (3)
C6	1.3693 (3)	0.6554 (3)	0.74291 (10)	0.0187 (3)
C7	1.6509 (4)	0.9271 (3)	0.86434 (10)	0.0214 (4)
C8	1.7066 (3)	1.1854 (3)	0.90685 (10)	0.0204 (3)
H2	0.903 (4)	0.259 (4)	0.6804 (12)	0.025 (5)*
H4	0.789 (4)	0.887 (3)	0.5248 (11)	0.023 (4)*
H5	1.215 (4)	0.970 (4)	0.6343 (12)	0.029 (5)*
H6A	1.556 (4)	0.658 (3)	0.7197 (11)	0.021 (4)*
H6B	1.327 (4)	0.527 (3)	0.7796 (12)	0.024 (4)*
H7A	1.594 (4)	0.813 (4)	0.9065 (12)	0.026 (5)*
H7B	1.843 (4)	0.916 (3)	0.8461 (12)	0.028 (5)*

	U11	U22	U33	U12	U13	U23
F1	0.0318 (5)	0.0225 (5)	0.0219 (5)	0.0071 (4)	−0.0072 (4)	−0.0029 (4)
F2	0.0381 (6)	0.0217 (5)	0.0283 (5)	0.0050 (4)	0.0051 (4)	0.0072 (4)
F3	0.0266 (5)	0.0305 (5)	0.0318 (5)	0.0125 (4)	0.0036 (4)	−0.0048 (4)
O	0.0264 (6)	0.0187 (5)	0.0205 (6)	0.0106 (4)	−0.0067 (5)	−0.0044 (4)
N	0.0208 (6)	0.0119 (6)	0.0188 (6)	0.0044 (5)	0.0024 (5)	0.0025 (5)
C1	0.0161 (7)	0.0164 (7)	0.0168 (7)	0.0063 (6)	0.0046 (6)	−0.0002 (6)
C2	0.0223 (8)	0.0126 (7)	0.0182 (7)	0.0065 (6)	0.0031 (6)	0.0027 (5)
C3	0.0162 (7)	0.0125 (7)	0.0156 (7)	0.0044 (5)	0.0054 (6)	0.0023 (5)
C4	0.0208 (7)	0.0133 (7)	0.0198 (7)	0.0035 (6)	0.0026 (6)	0.0055 (6)
C5	0.0187 (7)	0.0139 (7)	0.0217 (8)	0.0006 (6)	0.0028 (6)	0.0022 (6)
C6	0.0192 (7)	0.0156 (7)	0.0210 (8)	0.0061 (6)	0.0015 (6)	−0.0002 (6)
C7	0.0236 (8)	0.0205 (8)	0.0188 (8)	0.0084 (6)	−0.0033 (7)	0.0004 (6)
C8	0.0212 (8)	0.0209 (8)	0.0183 (7)	0.0074 (6)	−0.0008 (6)	0.0015 (6)

F1—C8	1.3386 (17)	C3—C4	1.396 (2)
F2—C8	1.3411 (18)	C3—C3i	1.481 (3)
F3—C8	1.3347 (18)	C4—C5	1.377 (2)
O—C7	1.4053 (18)	C4—H4	0.926 (19)
O—C6	1.4304 (17)	C5—H5	0.96 (2)
N—C2	1.3322 (19)	C6—H6A	0.990 (19)
N—C3	1.3446 (18)	C6—H6B	0.960 (19)
C1—C5	1.390 (2)	C7—C8	1.505 (2)
C1—C2	1.394 (2)	C7—H7A	0.98 (2)
C1—C6	1.494 (2)	C7—H7B	1.00 (2)
C2—H2	0.96 (2)
C7—O—C6	111.24 (11)	O—C6—H6A	108.1 (10)
C2—N—C3	117.65 (12)	C1—C6—H6A	110.2 (10)
C5—C1—C2	117.07 (14)	O—C6—H6B	109.2 (11)
C5—C1—C6	122.24 (13)	C1—C6—H6B	110.7 (11)
C2—C1—C6	120.69 (13)	H6A—C6—H6B	109.9 (14)
N—C2—C1	124.41 (13)	O—C7—C8	107.27 (12)
N—C2—H2	115.6 (11)	O—C7—H7A	111.5 (11)
C1—C2—H2	119.9 (11)	C8—C7—H7A	108.4 (11)
N—C3—C4	122.04 (13)	O—C7—H7B	111.4 (10)
N—C3—C3i	117.10 (15)	C8—C7—H7B	107.4 (11)
C4—C3—C3i	120.85 (15)	H7A—C7—H7B	110.6 (16)
C5—C4—C3	119.25 (13)	F3—C8—F1	107.01 (12)
C5—C4—H4	122.6 (11)	F3—C8—F2	106.48 (12)
C3—C4—H4	118.2 (11)	F1—C8—F2	107.15 (12)
C4—C5—C1	119.49 (14)	F3—C8—C7	112.67 (13)
C4—C5—H5	119.0 (11)	F1—C8—C7	110.74 (12)
C1—C5—H5	121.5 (11)	F2—C8—C7	112.46 (13)
O—C6—C1	108.60 (11)
C3—N—C2—C1	−1.6 (2)	C6—C1—C5—C4	−179.74 (13)
C5—C1—C2—N	1.9 (2)	C7—O—C6—C1	177.45 (12)
C6—C1—C2—N	−177.87 (13)	C5—C1—C6—O	41.49 (19)
C2—N—C3—C4	−1.1 (2)	C2—C1—C6—O	−138.72 (14)
C2—N—C3—C3i	179.43 (14)	C6—O—C7—C8	174.02 (13)
N—C3—C4—C5	3.4 (2)	O—C7—C8—F3	52.09 (17)
C3i—C3—C4—C5	−177.17 (15)	O—C7—C8—F1	171.89 (12)
C3—C4—C5—C1	−3.0 (2)	O—C7—C8—F2	−68.27 (17)
C2—C1—C5—C4	0.5 (2)

Cg is the centroid of the N,C1–C5 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···Ni	0.925 (17)	2.464 (18)	2.809 (2)	102.3 (12)
C6—H6A···Cgii	0.990 (19)	2.59	3.5089 (16)	155

	hpd(Å)	hcd(Å)	sa(°)
C6-H6A···πiii	2.57 (2)	2.59 (2)	6.4 (2)

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the N,C1–C5 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯Ni	0.925 (17)	2.464 (18)	2.809 (2)	102.3 (12)
C6—H6A⋯Cgii	0.990 (19)	2.59	3.5089 (16)	155

Symmetry codes: (i) ; (ii) .