1,1,1,5,5,5-Hexafluoro-2,4-dimeth-oxy-pentane-2,4-diol.

The title compound, C(7)H(10)F(6)O(4), was isolated as an unexpected product from a reaction of tantalum(V) methoxide with hexa-fluoro-acetyl-acetone in a methanol solution. The asymmetric unit consists of one half-mol-ecule with the middle C atom lying on a twofold axis. The crystal structure is stabilized by O-H⋯O and an array of C-H⋯F hydrogen-bonding inter-actions. These inter-actions link the mol-ecules into a stable supra-molecular three-dimensional network. The mol-ecules pack in a ribbon-like form in the ac plane as a result of these inter-actions.

Related literature

For metal complexes with acetyl­acetone derivatives, see: Viljoen et al. (2010 ▶); Steyn et al. (2008 ▶); Cole et al. (2005 ▶).

Experimental

Crystal data

C7H10F6O4

M = 272.15

Monoclinic,

a = 17.829 (5) Å

b = 6.713 (5) Å

c = 9.347 (5) Å

β = 109.509 (5)°

V = 1054.5 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 100 K

0.75 × 0.28 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.936, T max = 0.963

5850 measured reflections

1277 independent reflections

1049 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.079

S = 1.05

1277 reflections

98 parameters

All H-atom parameters refined

Δρmax = 0.39 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT-Plus (Bruker, 2007 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005) ▶; software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811044813/pv2464sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811044813/pv2464Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811044813/pv2464Isup3.cml

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

C7H10F6O4	F(000) = 552
Mr = 272.15	Dx = 1.714 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.829 (5) Å	Cell parameters from 2123 reflections
b = 6.713 (5) Å	θ = 3.3–28.1°
c = 9.347 (5) Å	µ = 0.20 mm−1
β = 109.509 (5)°	T = 100 K
V = 1054.5 (10) Å3	Needle, colourless
Z = 4	0.75 × 0.28 × 0.19 mm

Bruker APEXII CCD diffractometer	1049 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 28°, θmin = 3.8°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −23→21
Tmin = 0.936, Tmax = 0.963	k = −8→8
5850 measured reflections	l = −11→12
1277 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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079	All H-atom parameters refined
S = 1.05	w = 1/[σ2(Fo2) + (0.0386P)2 + 0.4659P] where P = (Fo2 + 2Fc2)/3
1277 reflections	(Δ/σ)max < 0.001
98 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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 > 2σ(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	0.67222 (4)	0.00201 (11)	0.36009 (8)	0.0251 (2)
F2	0.61085 (5)	−0.06716 (11)	0.12475 (8)	0.0263 (2)
F3	0.69105 (4)	0.18291 (12)	0.18451 (9)	0.0286 (2)
O1	0.59145 (5)	0.34897 (12)	0.35035 (9)	0.0176 (2)
O2	0.54269 (5)	0.31437 (13)	0.08511 (9)	0.0192 (2)
C1	0.63589 (7)	0.08280 (19)	0.22390 (13)	0.0192 (3)
C2	0.56606 (7)	0.21774 (18)	0.22550 (12)	0.0153 (3)
C3	0.5	0.0899 (2)	0.25	0.0150 (3)
C4	0.64796 (10)	0.5018 (2)	0.34926 (19)	0.0311 (3)
H3	0.4785 (8)	0.008 (2)	0.1636 (14)	0.016 (3)*
H4A	0.6446 (9)	0.598 (3)	0.4222 (18)	0.032 (4)*
H4B	0.6369 (10)	0.559 (3)	0.251 (2)	0.043 (5)*
H4C	0.7027 (13)	0.450 (3)	0.383 (2)	0.056 (6)*
H2	0.4960 (10)	0.351 (3)	0.0706 (18)	0.036 (5)*

	U11	U22	U33	U12	U13	U23
F1	0.0227 (4)	0.0299 (4)	0.0202 (4)	0.0092 (3)	0.0038 (3)	0.0038 (3)
F2	0.0285 (4)	0.0259 (4)	0.0241 (4)	0.0068 (3)	0.0083 (3)	−0.0070 (3)
F3	0.0198 (4)	0.0341 (5)	0.0382 (5)	0.0039 (3)	0.0179 (3)	0.0044 (3)
O1	0.0171 (4)	0.0168 (4)	0.0207 (4)	−0.0048 (3)	0.0085 (3)	−0.0045 (3)
O2	0.0164 (5)	0.0238 (5)	0.0187 (4)	0.0031 (4)	0.0076 (3)	0.0064 (3)
C1	0.0181 (6)	0.0226 (6)	0.0171 (6)	0.0024 (5)	0.0062 (5)	−0.0007 (4)
C2	0.0159 (6)	0.0162 (5)	0.0143 (6)	0.0011 (4)	0.0057 (4)	0.0001 (4)
C3	0.0149 (8)	0.0148 (8)	0.0152 (8)	0	0.0049 (6)	0
C4	0.0336 (8)	0.0291 (8)	0.0342 (8)	−0.0165 (6)	0.0159 (7)	−0.0074 (6)

F1—C1	1.3354 (15)	C1—C2	1.5438 (17)
F2—C1	1.3399 (16)	C2—C3	1.5352 (15)
F3—C1	1.3402 (15)	C3—C2i	1.5352 (15)
O1—C2	1.4107 (15)	C3—H3	0.945 (13)
O1—C4	1.4405 (17)	C4—H4A	0.954 (17)
O2—C2	1.3968 (15)	C4—H4B	0.950 (17)
O2—H2	0.835 (17)	C4—H4C	0.98 (2)
C2—O1—C4	118.10 (10)	O1—C2—C1	109.72 (9)
C2—O2—H2	104.9 (11)	C3—C2—C1	109.55 (11)
F1—C1—F2	107.32 (11)	C2—C3—C2i	112.00 (14)
F1—C1—F3	107.38 (10)	C2—C3—H3	108.1 (8)
F2—C1—F3	107.00 (10)	C2i—C3—H3	109.8 (8)
F1—C1—C2	111.41 (10)	O1—C4—H4A	105.3 (10)
F2—C1—C2	111.35 (10)	O1—C4—H4B	111.8 (11)
F3—C1—C2	112.12 (11)	H4A—C4—H4B	112.1 (14)
O2—C2—O1	113.56 (11)	O1—C4—H4C	111.7 (12)
O2—C2—C3	113.38 (9)	H4A—C4—H4C	107.4 (15)
O1—C2—C3	106.02 (9)	H4B—C4—H4C	108.4 (15)
O2—C2—C1	104.60 (9)
C4—O1—C2—O2	−48.50 (14)	F3—C1—C2—O1	−71.61 (13)
C4—O1—C2—C3	−173.64 (11)	F1—C1—C2—C3	−67.23 (11)
C4—O1—C2—C1	68.14 (14)	F2—C1—C2—C3	52.54 (12)
F1—C1—C2—O2	170.92 (9)	F3—C1—C2—C3	172.38 (8)
F2—C1—C2—O2	−69.30 (12)	O2—C2—C3—C2i	−71.42 (8)
F3—C1—C2—O2	50.54 (12)	O1—C2—C3—C2i	53.84 (6)
F1—C1—C2—O1	48.77 (13)	C1—C2—C3—C2i	172.17 (10)
F2—C1—C2—O1	168.55 (9)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.835 (17)	1.935 (17)	2.6648 (14)	145.4 (16)
O2—H2···O2ii	0.835 (17)	2.640 (17)	3.073 (2)	113.7 (14)
C4—H4A···F3iii	0.954 (17)	2.741 (17)	3.644 (2)	158.4 (13)
C3—H3···F2iv	0.945 (13)	2.663 (13)	3.4022 (17)	135.5 (10)
C4—H4A···F1v	0.954 (17)	2.853 (17)	3.383 (3)	116.1 (11)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.835 (17)	1.935 (17)	2.6648 (14)	145.4 (16)
O2—H2⋯O2ii	0.835 (17)	2.640 (17)	3.073 (2)	113.7 (14)
C4—H4A⋯F3iii	0.954 (17)	2.741 (17)	3.644 (2)	158.4 (13)
C3—H3⋯F2iv	0.945 (13)	2.663 (13)	3.4022 (17)	135.5 (10)
C4—H4A⋯F1v	0.954 (17)	2.853 (17)	3.383 (3)	116.1 (11)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .