1,5-Bis(penta­fluoro­phen­yl)-3-phenyl­pent-2-ene-1,5-dione

Schwarzer, A.; Weber, E.

doi:10.1107/S1600536809041701

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2801

https://doi.org/10.1107/S1600536809041701

Open

access

1,5-Bis(pentafluorophenyl)-3-phenylpent-2-ene-1,5-dione

Anke Schwarzer ^a and Edwin Weber ^a ^*

^aInstitut für Organische Chemie, TU Bergakademie Freiberg, Leipziger Strasse 29, D-09596 Freiberg/Sachsen, Germany
^*Correspondence e-mail: edwin.weber@chemie.tu-freiberg.de

(Received 30 September 2009; accepted 12 October 2009; online 23 October 2009)

In the title compound, C₂₃H₈F₁₀O₂, the three arene rings are twisted one with respect to the other: the two perfluorinated arene rings are tilted to each other by an angle of 60.39 (7)°. They are inclined to the non-fluorinated phenyl unit by 38.85 (7) and 78.74 (7)°. The olefinic double bond adopts an E configuration. The carbonyl groups are not in a coplanar alignment with reference to the neighbouring arene rings. The crystal packing features a number of weak C—H⋯F interactions, which leads to the formation of a three-dimensional network.

Related literature

For a detailed discussion of fluorinated chalcones, see: Cesarin-Sobrinho et al. (2001 ); Cesarin-Sobrinho & Netto-Ferreira (2002 ).

Experimental

Crystal data

C₂₃H₈F₁₀O₂
M_r = 506.29
Monoclinic, P 2₁ /c
a = 10.9860 (3) Å
b = 15.8843 (4) Å
c = 11.4963 (3) Å
β = 101.528 (1)°
V = 1965.69 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 93 K
0.46 × 0.43 × 0.41 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
18281 measured reflections
3657 independent reflections
3210 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.092
S = 1.03
3657 reflections
316 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯F7ⁱ	0.95	2.54	3.4393 (17)	159
C16—H16B⋯F2ⁱⁱ	0.99	2.46	3.4004 (15)	159
C11—H11⋯F9ⁱⁱⁱ	0.95	2.56	3.2326 (18)	128
Symmetry codes: (i) x-1, y, z-1; (ii) x-1, y, z; (iii) -x, -y+1, -z+1.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809041701/su2150sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809041701/su2150Isup2.hkl

checkCIF report

Comment top

The title compound (Fig. 1) exhibits a non-planar structure, which can be described by the dihedral and torsion angles of the arene rings and carbonyl groups with respect to one another. While the two perfluorinated arene rings A (C1-C6) and C (C18-C23) are tilted to each other at an angle of 60.39 (7) °, they are inclined to the non-fluorinated phenyl ring B (C10-C15) by 38.85 (7) and 78.74 (7)°, respectively. The carbonyl groups are tilted with reference to the adjacent perfluoro arene units, with torsion angles C1-C6-C7-O1 and O2-C17-C18-C19 being 37.76 (19)° and 43.27 (18) °, respectively. The olefinic double bond is fixed in the (E)-configuration.

In the crystal structure of the title compound adjacent molecules are linked by two C—H···F contacts (C13-H13···F7ⁱ and C11-H11···F9ⁱⁱ), so forming a two dimensional network parallel to the ac plane [Table 1 and Fig. 2]. A third C-H···F interaction (C16-H16B···F2ⁱⁱⁱ) links these planes to form a three dimensional network. Although two polar carbonyl groups are present in the molecule, their oxygen atoms are not involved in the formation of intermolecular contacts.

Related literature top

For a detailed discussion of fluorinated chalcones, see: Cesarin-Sobrinho et al. (2001); Cesarin-Sobrinho & Netto-Ferreira (2002).

Experimental top

The title compound was obtained as a by-product during the synthesis of pentafluorochalcone from a 1:1 mixture of 2,3,4,5,6-pentafluoroacetophenone and benzaldehyde dissolved in sulfuric acid. After separation of the main product colourless single crystals were isolated from the filtrate on slow evaporation in air at rt.

Structure description top

For a detailed discussion of fluorinated chalcones, see: Cesarin-Sobrinho et al. (2001); Cesarin-Sobrinho & Netto-Ferreira (2002).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the molecular structure of the title compound, showing 50% probability displacement ellipsoids.
	Fig. 2. A partial view of the crystal packing, viewed along the b axis, of the title compound. C—H···F contacts as shown as broken lines - see Table 1 for details [Non-relevant H atoms have been omitted for clarity].

1,5-Bis(pentafluorophenyl)-3-phenylpent-2-ene-1,5-dione top

Crystal data top

C₂₃H₈F₁₀O₂	F(000) = 1008
M_r = 506.29	D_x = 1.711 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5070 reflections
a = 10.9860 (3) Å	θ = 3.1–36.1°
b = 15.8843 (4) Å	µ = 0.17 mm⁻¹
c = 11.4963 (3) Å	T = 93 K
β = 101.528 (1)°	Plate, colourless
V = 1965.69 (9) Å³	0.46 × 0.43 × 0.41 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3210 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.019
Graphite monochromator	θ_max = 25.5°, θ_min = 1.9°
phi and ω scans	h = −13→13
18281 measured reflections	k = −19→17
3657 independent reflections	l = −13→13

Refinement top

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) = 0.092	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0587P)² + 0.6558P] where P = (F_o² + 2F_c²)/3
3657 reflections	(Δ/σ)_max < 0.001
316 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₃H₈F₁₀O₂	V = 1965.69 (9) Å³
M_r = 506.29	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.9860 (3) Å	µ = 0.17 mm⁻¹
b = 15.8843 (4) Å	T = 93 K
c = 11.4963 (3) Å	0.46 × 0.43 × 0.41 mm
β = 101.528 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3210 reflections with I > 2σ(I)
18281 measured reflections	R_int = 0.019
3657 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.092	H-atom parameters constrained
S = 1.03	Δρ_max = 0.28 e Å⁻³
3657 reflections	Δρ_min = −0.20 e Å⁻³
316 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.26093 (9)	0.41039 (7)	0.53299 (8)	0.0240 (2)
O2	0.09160 (9)	0.23393 (6)	0.54477 (9)	0.0243 (2)
F1	0.49682 (7)	0.36112 (5)	0.53619 (7)	0.0238 (2)
F2	0.69999 (7)	0.39896 (6)	0.45459 (8)	0.0303 (2)
F3	0.68309 (8)	0.48896 (6)	0.24995 (8)	0.0302 (2)
F4	0.45871 (8)	0.54586 (6)	0.13327 (8)	0.0314 (2)
F5	0.25233 (7)	0.50954 (6)	0.21465 (7)	0.0272 (2)
F6	0.32482 (8)	0.25147 (6)	0.68712 (8)	0.0307 (2)
F7	0.43936 (9)	0.29180 (7)	0.90694 (10)	0.0468 (3)
F8	0.32401 (12)	0.38979 (7)	1.04497 (8)	0.0531 (3)
F9	0.08804 (12)	0.44422 (6)	0.96211 (8)	0.0453 (3)
F10	−0.02794 (8)	0.40693 (6)	0.73839 (8)	0.0308 (2)
C1	0.48305 (12)	0.40581 (8)	0.43569 (12)	0.0184 (3)
C2	0.58917 (12)	0.42447 (9)	0.39365 (13)	0.0211 (3)
C3	0.58098 (12)	0.47069 (9)	0.29088 (13)	0.0220 (3)
C4	0.46655 (13)	0.49898 (9)	0.23136 (12)	0.0218 (3)
C5	0.36102 (12)	0.47898 (9)	0.27382 (12)	0.0196 (3)
C6	0.36584 (12)	0.43131 (8)	0.37599 (12)	0.0178 (3)
C7	0.25245 (12)	0.40885 (8)	0.42556 (12)	0.0187 (3)
C8	0.14008 (12)	0.38285 (8)	0.34137 (12)	0.0184 (3)
H8	0.1444	0.3779	0.2599	0.022*
C9	0.03089 (12)	0.36557 (8)	0.37313 (12)	0.0173 (3)
C10	−0.07770 (12)	0.34003 (9)	0.28121 (12)	0.0186 (3)
C11	−0.09786 (12)	0.37620 (9)	0.16798 (12)	0.0216 (3)
H11	−0.0407	0.4165	0.1495	0.026*
C12	−0.20054 (14)	0.35365 (10)	0.08255 (13)	0.0277 (3)
H12	−0.2144	0.3793	0.0064	0.033*
C13	−0.28304 (14)	0.29369 (11)	0.10805 (15)	0.0340 (4)
H13	−0.3531	0.2780	0.0493	0.041*
C14	−0.26309 (14)	0.25668 (11)	0.21924 (16)	0.0346 (4)
H14	−0.3192	0.2151	0.2362	0.042*
C15	−0.16197 (13)	0.27982 (10)	0.30601 (14)	0.0256 (3)
H15	−0.1499	0.2548	0.3825	0.031*
C16	0.01318 (12)	0.37282 (9)	0.50062 (12)	0.0187 (3)
H16A	0.0422	0.4289	0.5322	0.022*
H16B	−0.0764	0.3683	0.5019	0.022*
C17	0.08369 (11)	0.30502 (8)	0.58018 (12)	0.0176 (3)
C18	0.14383 (12)	0.32769 (8)	0.70533 (12)	0.0191 (3)
C19	0.26301 (13)	0.29878 (9)	0.75257 (13)	0.0234 (3)
C20	0.32346 (15)	0.31974 (10)	0.86547 (14)	0.0310 (4)
C23	0.08752 (13)	0.37790 (9)	0.77799 (13)	0.0234 (3)
C22	0.14702 (17)	0.39821 (9)	0.89257 (13)	0.0312 (4)
C21	0.26522 (17)	0.36956 (10)	0.93524 (13)	0.0345 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0200 (5)	0.0339 (6)	0.0175 (5)	−0.0065 (4)	0.0026 (4)	−0.0014 (4)
O2	0.0289 (5)	0.0193 (5)	0.0244 (5)	0.0001 (4)	0.0045 (4)	−0.0027 (4)
F1	0.0226 (4)	0.0249 (4)	0.0223 (4)	0.0012 (3)	0.0007 (3)	0.0039 (3)
F2	0.0149 (4)	0.0330 (5)	0.0416 (5)	0.0055 (3)	0.0023 (3)	0.0001 (4)
F3	0.0225 (4)	0.0350 (5)	0.0374 (5)	−0.0061 (4)	0.0164 (4)	−0.0056 (4)
F4	0.0339 (5)	0.0360 (5)	0.0254 (5)	−0.0083 (4)	0.0086 (4)	0.0075 (4)
F5	0.0192 (4)	0.0343 (5)	0.0262 (4)	0.0008 (3)	0.0003 (3)	0.0086 (4)
F6	0.0234 (4)	0.0285 (5)	0.0384 (5)	0.0074 (3)	0.0019 (4)	0.0002 (4)
F7	0.0413 (6)	0.0345 (6)	0.0506 (6)	−0.0048 (4)	−0.0248 (5)	0.0138 (5)
F8	0.0928 (9)	0.0368 (6)	0.0194 (5)	−0.0223 (6)	−0.0137 (5)	0.0026 (4)
F9	0.0897 (8)	0.0268 (5)	0.0263 (5)	−0.0026 (5)	0.0279 (5)	−0.0046 (4)
F10	0.0317 (5)	0.0309 (5)	0.0343 (5)	0.0057 (4)	0.0172 (4)	−0.0005 (4)
C1	0.0190 (7)	0.0165 (7)	0.0191 (7)	−0.0013 (5)	0.0024 (5)	−0.0026 (5)
C2	0.0155 (6)	0.0198 (7)	0.0271 (7)	0.0012 (5)	0.0023 (5)	−0.0067 (6)
C3	0.0192 (7)	0.0221 (7)	0.0276 (8)	−0.0051 (5)	0.0116 (6)	−0.0080 (6)
C4	0.0265 (7)	0.0213 (7)	0.0182 (7)	−0.0052 (5)	0.0060 (6)	−0.0010 (5)
C5	0.0169 (6)	0.0214 (7)	0.0194 (7)	−0.0009 (5)	0.0005 (5)	−0.0021 (5)
C6	0.0170 (6)	0.0180 (7)	0.0184 (7)	−0.0021 (5)	0.0036 (5)	−0.0038 (5)
C7	0.0177 (6)	0.0177 (7)	0.0206 (7)	−0.0008 (5)	0.0037 (5)	0.0003 (5)
C8	0.0183 (6)	0.0196 (7)	0.0167 (7)	−0.0009 (5)	0.0024 (5)	0.0001 (5)
C9	0.0183 (6)	0.0145 (6)	0.0183 (7)	0.0023 (5)	0.0016 (5)	0.0009 (5)
C10	0.0149 (6)	0.0197 (7)	0.0206 (7)	0.0024 (5)	0.0019 (5)	−0.0030 (5)
C11	0.0190 (6)	0.0232 (7)	0.0219 (7)	0.0023 (5)	0.0024 (5)	−0.0022 (5)
C12	0.0268 (8)	0.0315 (8)	0.0217 (7)	0.0067 (6)	−0.0030 (6)	−0.0048 (6)
C13	0.0223 (7)	0.0379 (9)	0.0358 (9)	0.0000 (6)	−0.0083 (6)	−0.0116 (7)
C14	0.0231 (8)	0.0336 (9)	0.0449 (10)	−0.0102 (6)	0.0014 (7)	−0.0044 (7)
C15	0.0216 (7)	0.0266 (8)	0.0275 (8)	−0.0029 (6)	0.0025 (6)	0.0010 (6)
C16	0.0155 (6)	0.0212 (7)	0.0192 (7)	0.0008 (5)	0.0032 (5)	−0.0014 (5)
C17	0.0141 (6)	0.0201 (7)	0.0196 (7)	−0.0014 (5)	0.0062 (5)	−0.0006 (5)
C18	0.0232 (7)	0.0165 (7)	0.0179 (7)	−0.0032 (5)	0.0049 (5)	0.0021 (5)
C19	0.0258 (7)	0.0181 (7)	0.0250 (8)	−0.0019 (5)	0.0016 (6)	0.0038 (6)
C20	0.0342 (8)	0.0221 (8)	0.0301 (8)	−0.0071 (6)	−0.0094 (6)	0.0096 (6)
C23	0.0301 (7)	0.0187 (7)	0.0232 (7)	−0.0025 (6)	0.0096 (6)	0.0032 (6)
C22	0.0599 (11)	0.0179 (7)	0.0189 (7)	−0.0071 (7)	0.0154 (7)	−0.0008 (6)
C21	0.0597 (11)	0.0236 (8)	0.0150 (7)	−0.0159 (7)	−0.0044 (7)	0.0044 (6)

Geometric parameters (Å, º) top

O1—C7	1.2202 (17)	C9—C16	1.5210 (18)
O2—C17	1.2095 (17)	C10—C11	1.399 (2)
F1—C1	1.3386 (16)	C10—C15	1.399 (2)
F2—C2	1.3403 (16)	C11—C12	1.386 (2)
F3—C3	1.3322 (15)	C11—H11	0.9500
F4—C4	1.3397 (16)	C12—C13	1.386 (2)
F5—C5	1.3415 (16)	C12—H12	0.9500
F6—C19	1.3403 (17)	C13—C14	1.384 (2)
F7—C20	1.3427 (19)	C13—H13	0.9500
F8—C21	1.3365 (18)	C14—C15	1.386 (2)
F9—C22	1.3416 (18)	C14—H14	0.9500
F10—C23	1.3409 (17)	C15—H15	0.9500
C1—C2	1.3805 (19)	C16—C17	1.5208 (18)
C1—C6	1.3928 (19)	C16—H16A	0.9900
C2—C3	1.379 (2)	C16—H16B	0.9900
C3—C4	1.381 (2)	C17—C18	1.5021 (18)
C4—C5	1.3818 (19)	C18—C23	1.387 (2)
C5—C6	1.3896 (19)	C18—C19	1.391 (2)
C6—C7	1.5125 (18)	C19—C20	1.375 (2)
C7—C8	1.4676 (18)	C20—C21	1.373 (3)
C8—C9	1.3500 (19)	C23—C22	1.386 (2)
C8—H8	0.9500	C22—C21	1.371 (3)
C9—C10	1.4834 (18)

F1—C1—C2	117.28 (12)	C14—C13—C12	119.85 (14)
F1—C1—C6	120.89 (12)	C14—C13—H13	120.1
C2—C1—C6	121.83 (13)	C12—C13—H13	120.1
F2—C2—C3	120.39 (12)	C13—C14—C15	120.54 (15)
F2—C2—C1	119.64 (13)	C13—C14—H14	119.7
C3—C2—C1	119.96 (13)	C15—C14—H14	119.7
F3—C3—C2	120.22 (13)	C14—C15—C10	120.15 (14)
F3—C3—C4	120.10 (13)	C14—C15—H15	119.9
C2—C3—C4	119.67 (12)	C10—C15—H15	119.9
F4—C4—C3	119.80 (12)	C17—C16—C9	112.21 (11)
F4—C4—C5	120.52 (13)	C17—C16—H16A	109.2
C3—C4—C5	119.68 (13)	C9—C16—H16A	109.2
F5—C5—C4	117.54 (12)	C17—C16—H16B	109.2
F5—C5—C6	120.36 (12)	C9—C16—H16B	109.2
C4—C5—C6	122.07 (13)	H16A—C16—H16B	107.9
C5—C6—C1	116.76 (12)	O2—C17—C18	119.92 (12)
C5—C6—C7	123.49 (12)	O2—C17—C16	121.40 (12)
C1—C6—C7	119.72 (12)	C18—C17—C16	118.68 (11)
O1—C7—C8	123.86 (12)	C23—C18—C19	116.93 (13)
O1—C7—C6	118.34 (12)	C23—C18—C17	123.44 (12)
C8—C7—C6	117.74 (11)	C19—C18—C17	119.62 (12)
C9—C8—C7	123.69 (12)	F6—C19—C20	117.53 (13)
C9—C8—H8	118.2	F6—C19—C18	120.58 (12)
C7—C8—H8	118.2	C20—C19—C18	121.85 (14)
C8—C9—C10	119.63 (12)	F7—C20—C21	120.18 (14)
C8—C9—C16	122.47 (12)	F7—C20—C19	119.99 (16)
C10—C9—C16	117.88 (11)	C21—C20—C19	119.83 (15)
C11—C10—C15	118.81 (12)	F10—C23—C22	118.49 (13)
C11—C10—C9	120.37 (12)	F10—C23—C18	119.92 (13)
C15—C10—C9	120.82 (12)	C22—C23—C18	121.58 (14)
C12—C11—C10	120.53 (14)	F9—C22—C21	120.22 (15)
C12—C11—H11	119.7	F9—C22—C23	120.05 (16)
C10—C11—H11	119.7	C21—C22—C23	119.72 (15)
C13—C12—C11	120.11 (14)	F8—C21—C22	120.16 (16)
C13—C12—H12	119.9	F8—C21—C20	119.76 (16)
C11—C12—H12	119.9	C22—C21—C20	120.07 (14)

F1—C1—C2—F2	−1.07 (19)	C10—C11—C12—C13	−1.2 (2)
C6—C1—C2—F2	179.64 (12)	C11—C12—C13—C14	0.4 (2)
F1—C1—C2—C3	−179.66 (12)	C12—C13—C14—C15	0.8 (3)
C6—C1—C2—C3	1.0 (2)	C13—C14—C15—C10	−1.1 (2)
F2—C2—C3—F3	1.4 (2)	C11—C10—C15—C14	0.2 (2)
C1—C2—C3—F3	179.93 (12)	C9—C10—C15—C14	179.92 (14)
F2—C2—C3—C4	−177.77 (12)	C8—C9—C16—C17	−69.80 (16)
C1—C2—C3—C4	0.8 (2)	C10—C9—C16—C17	111.38 (13)
F3—C3—C4—F4	−1.0 (2)	C9—C16—C17—O2	−37.89 (17)
C2—C3—C4—F4	178.17 (12)	C9—C16—C17—C18	142.37 (12)
F3—C3—C4—C5	179.33 (12)	O2—C17—C18—C23	−137.78 (14)
C2—C3—C4—C5	−1.5 (2)	C16—C17—C18—C23	41.95 (18)
F4—C4—C5—F5	−1.3 (2)	O2—C17—C18—C19	43.27 (18)
C3—C4—C5—F5	178.44 (12)	C16—C17—C18—C19	−136.99 (13)
F4—C4—C5—C6	−179.26 (12)	C23—C18—C19—F6	−178.52 (12)
C3—C4—C5—C6	0.5 (2)	C17—C18—C19—F6	0.49 (19)
F5—C5—C6—C1	−176.62 (12)	C23—C18—C19—C20	−0.9 (2)
C4—C5—C6—C1	1.3 (2)	C17—C18—C19—C20	178.13 (13)
F5—C5—C6—C7	1.5 (2)	F6—C19—C20—F7	−1.1 (2)
C4—C5—C6—C7	179.47 (13)	C18—C19—C20—F7	−178.76 (13)
F1—C1—C6—C5	178.66 (12)	F6—C19—C20—C21	178.63 (13)
C2—C1—C6—C5	−2.1 (2)	C18—C19—C20—C21	0.9 (2)
F1—C1—C6—C7	0.43 (19)	C19—C18—C23—F10	−179.14 (12)
C2—C1—C6—C7	179.71 (12)	C17—C18—C23—F10	1.9 (2)
C5—C6—C7—O1	−140.34 (14)	C19—C18—C23—C22	−0.2 (2)
C1—C6—C7—O1	37.76 (19)	C17—C18—C23—C22	−179.15 (13)
C5—C6—C7—C8	42.30 (19)	F10—C23—C22—F9	1.6 (2)
C1—C6—C7—C8	−139.60 (13)	C18—C23—C22—F9	−177.41 (13)
O1—C7—C8—C9	6.5 (2)	F10—C23—C22—C21	−179.82 (13)
C6—C7—C8—C9	−176.30 (13)	C18—C23—C22—C21	1.2 (2)
C7—C8—C9—C10	179.78 (12)	F9—C22—C21—F8	−2.3 (2)
C7—C8—C9—C16	1.0 (2)	C23—C22—C21—F8	179.05 (13)
C8—C9—C10—C11	−36.74 (19)	F9—C22—C21—C20	177.44 (14)
C16—C9—C10—C11	142.12 (13)	C23—C22—C21—C20	−1.2 (2)
C8—C9—C10—C15	143.55 (14)	F7—C20—C21—F8	−0.4 (2)
C16—C9—C10—C15	−37.59 (18)	C19—C20—C21—F8	179.91 (13)
C15—C10—C11—C12	0.9 (2)	F7—C20—C21—C22	179.82 (13)
C9—C10—C11—C12	−178.77 (13)	C19—C20—C21—C22	0.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···F7ⁱ	0.95	2.54	3.4393 (17)	159
C16—H16B···F2ⁱⁱ	0.99	2.46	3.4004 (15)	159
C11—H11···F9ⁱⁱⁱ	0.95	2.56	3.2326 (18)	128

Symmetry codes: (i) x−1, y, z−1; (ii) x−1, y, z; (iii) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₃H₈F₁₀O₂
M_r	506.29
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	93
a, b, c (Å)	10.9860 (3), 15.8843 (4), 11.4963 (3)
β (°)	101.528 (1)
V (Å³)	1965.69 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.46 × 0.43 × 0.41

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	18281, 3657, 3210
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.092, 1.03
No. of reflections	3657
No. of parameters	316
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.20

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···F7ⁱ	0.95	2.54	3.4393 (17)	159
C16—H16B···F2ⁱⁱ	0.99	2.46	3.4004 (15)	159
C11—H11···F9ⁱⁱⁱ	0.95	2.56	3.2326 (18)	128

Symmetry codes: (i) x−1, y, z−1; (ii) x−1, y, z; (iii) −x, −y+1, −z+1.

References

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cesarin-Sobrinho, D. & Netto-Ferreira, J. C. (2002). Quim. Nova, 25, 62–68. CAS Google Scholar
Cesarin-Sobrinho, D., Netto-Ferreira, J. C. & Braz-Filho, R. (2001). Quim. Nova, 24, 604–611. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2801

https://doi.org/10.1107/S1600536809041701

Open

access