Fully and partially fluorinated flavone derivatives

In the crystal structures of the fully and partially fluorinated flavone derivatives 5,6,7,8-tetra­fluoro-2-(2,3,4,5,6-penta­fluoro­phen­yl)-4H-1-benzopyran-4-one, C₁₅HF₉O₂, (I), and 5,6,7,8-tetra­fluoro-2-phenyl-4H-1-benzopyran-4-one, C₁₅H₆F₄O₂, (II), the penta­fluoro­phenyl group and the pyran­one moiety in (I) are twisted due to repulsion of the F substituents, and a CO(δ⁻)...π(δ⁺) inter­molecular inter­action is observed between the carbonyl O atom and the penta­fluoro­phenyl group. In (II), on the other hand, the phenyl group and the pyran­one moiety are almost coplanar, and arene–perfluoro­arene inter­actions are observed in the head-to-tail inter­molecular columnar stacking between the phenyl group and the tetra­fluoro­phenyl­ene moiety.

S1. Comment

Flavone derivatives are one of the very important yellow pigments in natural plants. In particular, related compounds with the flavone framework have been widely investigated as unique biologically active reagents (Havsteen, 1983; Das & Rosazza, 2006). More than 100 flavone derivatives and nine naphthoflavone derivatives were found in a search of the Cambridge Structural Database (CSD, Version 5.30 of November 2008; Allen, 2002) and the crystal structure of flavone was determined by Waller et al. (2003). However, only two kinds of fluorinated flavone derivatives have been reported to date: 3-[1-(2,2-dimethylhydrazinylidene)ethyl]-6,7-difluoro-2-phenyl-4H-1-benzopyran-4-one (Vales et al., 2001) and 3-(4-fluorophenyl)-1H-naphtho[2,1-b]pyran-1-one (Neuman et al., 1989). Here, we report the first perfluorinated derivatives of the flavone framework, synthesized in order to understand the influence of fluorination effects on molecular structure and crystal packing, 5,6,7,8-tetrafluoro-2-(2,3,4,5,6-pentafluorophenyl)-4H-1-benzopyran-4-one, (I), and 5,6,7,8-tetrafluoro-2-phenyl-4H-1-benzopyran-4-one, (II).

Fully fluorinated aromatic compounds show an interaction with anion species (Quiñonero et al., 2002) and/or aromatic hydrocarbons (Patrick & Prosser, 1960; Williams, 1993; Hori et al., 2009), based on reversion of the charge orientation of the quadrupole moments compared with aromatic compounds. Accordingly, the three compounds (I), (II) and the non-fluorinated flavone (Waller et al., 2003) show completely different arrangements in these molecular packings. For example, three kinds of electrostatic interactions, dipole–π, arene–perfluoroarene and π–π interactions, are dominantly observed in (I), (II) and flavone, respectively.

The molecular structures of (I) and (II) are shown in Fig. 1. The molecule of (II) was found to be slightly disordered, with site-occupancy ratios of 0.938 (2) and 0.062 (2), respectively, for components A and B; only the major component, A, is shown here. In Fig. 2, the relationship between the disordered components A and B is shown. The minor B component is related to the major A component by an approximate twofold rotation about the molecular length. This sort of disorder is often found in planar molecules with weak intermolecular contacts (Ferguson et al., 1999). Hereinafter, we only discuss the major component, A. The hydrogen-bond geometries of (I) and component A of (II) are summarized in Tables 1 and 2, respectively. Selected bond lengths and angles for (I), component A of (II) and flavone (two crystallographically independent molecules, flavone-1 and flavone-2) are given in Table 3.

In the molecular structure of (I), the benzopyranone ring system (rings A and C) is planar and the r.m.s. deviation of atoms C1–C9/O1 is 0.018 Å. The pentafluorophenyl group and the pyranone moiety are highly twisted with respect to each other and the dihedral angle between the planes of the two rings defined by atoms C10–C15 (ring B) and C1–C3/O1/C4/C5 (ring C) is 52.78 (4)° (Fig. 1). On the other hand, in component A of (II), the phenyl group and the pyranone moiety are almost coplanar and the dihedral angle between the planes of the two rings defined by rings B and C is 7.88 (8)°, the benzopyranone ring system also being planar (r.m.s. deviation of the ten atoms is 0.015 Å). The difference can be explained by the repulsion of the F-substitution on atom C15. The carbonyl double bonds in (I) and component A of (II) are slightly [Text missing?] but significantly more localized than those in non-fluorinated flavone (Table 3). The C1—C5—C6 bond angles in the fluorinated compounds, (I) and component A of (II), are larger than those of non-fluorinated flavone. This is considered to be due to basic steric effects and electrostatic repulsion between atoms O2 and F1. Due to the influence of the F-substitution at F1, the C2—C1—C5 and C3—O1—C4 bond angles of the two fluorinated compounds are smaller than those of the non-fluorinated flavone (Table 3). The r.m.s. deviations of the structural overlay (Macrae et al., 2006) of the 12 atoms in the benzopyranone ring system (C1–C10/O1/O2) in (I), (II) and flavone are small, e.g. 0.04 Å between (I) and flavone-1 and (I) and flavone-2, and 0.03 Å between (II) and flavone-1, (II) and flavone-2, and (I) and (II).

The crystal packings of (I), (II) and flavone are quite different, as shown in Figs. 3, 4 and 5, respectively. In the crystal structure of (I), no remarkable intermolecular π–π stacking is observed for either the pentafluorophenyl group or the pyranone moiety, while the π planes of the pentafluorophenyl (B) and tetrafluorobenzopyranone (A and C) rings are arranged in an anti-parallel way. Carbonyl atom O2 at (x, y, z) interacts closely with a pentafluorophenyl group at (x + 1/2, -y + 1/2, z - 1/2), and vice versa the pentafluorophenyl group at (x, y, z) interacts with another carbonyl atom O2ⁱⁱⁱ [symmetry code: (iii) x - 1/2, -y + 1/2, z + 1/2]; the O2···CgBⁱⁱ distance [symmetry code: (ii) x + 1/2, -y + 1/2, z - 1/2] is 2.9228 (15) Å, where CgB is the centroid of the pentafluorophenyl ring B. Thus, the negative charge orientation of the O atom and the positive charge of the centroid of the fluorinated ring interact, which can be classified as a dipole–π interaction. Accordingly, the molecules are in a head-to-tail arrangement diagonally in the ac plane. Intermolecular C—F···π interactions are also observed, with distances between the F atoms and the ring centroids F4···CgB, F6···CgA and F9···CgC of 3.0765 (13), 3.1580 (13), and 3.1332 (13) Å, respectively. Intermolecular interactions induced by fluorination are also observed, which are the weak hydrogen bond (Desiraju, 1996; Thalladi et al., 1998) C2—H2···F5ⁱ [symmetry code: (i) x + 1, y, z; Table 1] and the dipole–dipole interaction between C1═ O2 and C9ⁱ—F4ⁱ [the C1···F4ⁱ and O2···C9ⁱ short intermolecular distances are 2.973 (2) and 2.916 (2) Å, respectively].

Intermolecular π–π interactions were clearly observed in the crystal structures of (II) and flavone, which are highly coplanar molecules. Both crystals show remarkable π–π stacking along the a axis to give columnar layers. In the layers, the carbonyl C═O groups are arranged in an interdigitating manner by the dipole–dipole repulsion in both structures. However, the structures of (II) and flavone are clearly different in their stacking positions. In (II), phenyl group B and tetrafluorophenylene moiety A interact closely by head-to-tail arrangement of the molecules, clearly showing an arene–perfluoroarene interaction; the intermolecular distances between the two centroids of the rings, CgC···CgCⁱⁱ [symmetry code: (ii) -x + 2, -y + 1, -z + 2] and CgA···CgBⁱⁱⁱ [symmetry code: (iii) -x + 1, -y + 1, -z + 2] are 3.5015 (11) and 3.5371 (12) Å, respectively. The corresponding perpendicular distances are 3.3605 (6) and 3.4481 (6) Å, respectively. In contrast, the phenyl groups are overlapped by a head-to-head arrangement of the flavones (Waller et al., 2003), showing π–π stacking; the intermolecular distances CgC···CgCⁱ [symmetry code: (i) x + 1/2, -y + 3/2, -z + 1] and CgB···CgBⁱ are 3.7904 (15) and 3.8128 (15) Å, respectively. The corresponding perpendicular distances are 3.4176 (7) and 3.4707 (7) Å, respectively. Thus, the phenyl group preferentially interacts with the tetrafluorophenylene moiety through an arene–perfluoroarene interaction, as opposed to with the phenyl group through a π–π interaction. In addition, the weak intermolecular hydrogen bond C12A—H12A···F2Aⁱ [symmetry code: (i) x - 1/2, -y + 3/2, z - 1/2] [Not the same symop (i) as above - please clarify] is observed in (II), as shown in Table 2. Intermolecular C—F···π interactions are also observed in (II), of the form C6A—F1A···CgBⁱⁱ, with F1A···CgBⁱⁱ = 3.3769 (16) Å and the C6A—F1A···CgBⁱⁱ angle = 86.32 (9)°.

S2. Experimental

The two fluorinated flavone derivatives were obtained from the elimination process of the corresponding dibenzoylmethanide derivatives. Crystals of (I) and (II) were obtained in poor yield from the synthetic processes involving bis(pentafluorobenzoyl)methane and benzoylpentafluorobenzoylmethane, respectively (Uhlemann et al., 1972; Hori et al., 2009). The compounds were crystallized by slow evaporation of an MeOH solution to give crystals suitable for X-ray crystallography.

S3. Refinement

For the disordered structure of (II), after refinement of the major component with unit occupancy, it was noted in a difference map in the molecular plane that there were a large number of small maxima in the 0.2–0.7 e Å^-3 range, which could be seen to be a minor component of (II) related to the major component by an approximate twofold rotation about the molecular length. The various minor peaks were then labelled B atoms to correspond exactly with the major A component. Refinement then continued with the major and minor occupancies refined as linked free variables, with the SAME command (SHELXL97; Sheldrick, 2008) employed to force the geometry of the minor component to conform with that of the major component. Atoms of the minor B component were refined isotropically, with one global U_iso value for the ring atoms and another U_iso value for the exocyclic atoms.

In both (I) and (II) all H atoms were placed in geometrically idealized positions and refined as riding, with aromatic C—H = 0.95 Å and with U_iso(H) = 1.2U_eq(C).

Computing details

For both compounds, data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); 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

	Fig. 1. (Top) The molecular structure of (I) and (bottom) that of component A of (II) at 100 K, showing the atom-labelling schemes. Displacement ellipsoids are drawn at the 50% probably level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The major (solid lines) and minor (open lines) components A and B of (II). The occupancy of component B is 6.2%. Displacement ellipsoids are drawn at the 50% probably level.
	Fig. 3. A view of part of the crystal structure of (I), approximately along the c axis.
	Fig. 4. A view of part of the crystal structure of (II), approximately along the a axis, showing the intermolecular columnar stacking through arene–perfluoroarene interactions.
	Fig. 5. A view of part of the crystal structure of flavone, approximately along the a axis, showing the head-to-head stacking through the phenyl moieties (Waller et al., 2003).

(I) 5,6,7,8-tetrafluoro-2-(2,3,4,5,6-pentafluorophenyl)-4H-1-benzopyran-4-one

Crystal data

C15HF9O2	F(000) = 752
Mr = 384.16	Dx = 1.929 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4991 reflections
a = 6.2221 (7) Å	θ = 3.2–27.7°
b = 25.234 (3) Å	µ = 0.21 mm^−1
c = 8.4624 (9) Å	T = 100 K
β = 95.355 (1)°	Plate, pale yellow
V = 1322.8 (2) Å^3	0.30 × 0.20 × 0.06 mm
Z = 4

Data collection

Bruker APEXII CCD area-detector diffractometer	2998 independent reflections
Radiation source: fine-focus sealed tube	2433 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 8.333 pixels mm^-1	θmax = 27.5°, θmin = 2.6°
ϕ and ω scans	h = −8→8
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	k = −32→32
Tmin = 0.939, Tmax = 0.987	l = −10→10
14615 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.094	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0399P)^2 + 0.7568P] where P = (Fo^2 + 2Fc^2)/3
2998 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

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 > 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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.47044 (17)	0.28350 (4)	0.86414 (13)	0.0216 (2)
O2	0.9748 (2)	0.35152 (5)	0.66183 (15)	0.0342 (3)
C1	0.8208 (3)	0.33202 (7)	0.7199 (2)	0.0260 (4)
C2	0.7914 (3)	0.27518 (7)	0.7334 (2)	0.0253 (4)
H2	0.8937	0.2522	0.6925	0.030*
C3	0.6258 (2)	0.25388 (6)	0.80134 (18)	0.0209 (3)
C4	0.4829 (3)	0.33742 (6)	0.85302 (18)	0.0212 (3)
C5	0.6485 (3)	0.36368 (7)	0.78325 (19)	0.0236 (3)
C6	0.6374 (3)	0.41904 (7)	0.7765 (2)	0.0291 (4)
C7	0.4739 (3)	0.44657 (7)	0.8372 (2)	0.0315 (4)
C8	0.3146 (3)	0.41949 (7)	0.9084 (2)	0.0292 (4)
C9	0.3195 (3)	0.36525 (7)	0.9166 (2)	0.0245 (3)
C10	0.5833 (3)	0.19674 (6)	0.81544 (19)	0.0212 (3)
C11	0.3860 (3)	0.17514 (6)	0.75820 (19)	0.0215 (3)
C12	0.3425 (3)	0.12197 (7)	0.7676 (2)	0.0246 (4)
C13	0.4990 (3)	0.08787 (7)	0.8354 (2)	0.0264 (4)
C14	0.6979 (3)	0.10787 (7)	0.8915 (2)	0.0268 (4)
C15	0.7377 (3)	0.16150 (7)	0.8818 (2)	0.0242 (3)
F1	0.78575 (19)	0.44679 (4)	0.70727 (14)	0.0413 (3)
F2	0.4661 (2)	0.49931 (4)	0.82780 (14)	0.0431 (3)
F3	0.15662 (19)	0.44623 (4)	0.96917 (14)	0.0392 (3)
F4	0.16640 (16)	0.33909 (4)	0.98643 (12)	0.0293 (2)
F5	0.23387 (15)	0.20657 (4)	0.68324 (12)	0.0276 (2)
F6	0.15002 (16)	0.10308 (4)	0.70889 (13)	0.0344 (3)
F7	0.45777 (18)	0.03650 (4)	0.84682 (13)	0.0369 (3)
F8	0.84812 (18)	0.07552 (4)	0.96071 (13)	0.0380 (3)
F9	0.93097 (16)	0.17974 (4)	0.94313 (13)	0.0340 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0211 (6)	0.0197 (6)	0.0247 (6)	−0.0012 (4)	0.0064 (5)	−0.0009 (4)
O2	0.0305 (7)	0.0442 (8)	0.0292 (7)	−0.0115 (6)	0.0092 (5)	0.0026 (6)
C1	0.0244 (8)	0.0339 (9)	0.0196 (8)	−0.0064 (7)	0.0010 (7)	0.0009 (7)
C2	0.0210 (8)	0.0322 (9)	0.0231 (8)	0.0011 (7)	0.0039 (6)	−0.0012 (7)
C3	0.0194 (8)	0.0246 (8)	0.0185 (8)	0.0022 (6)	0.0012 (6)	−0.0013 (6)
C4	0.0247 (8)	0.0201 (8)	0.0182 (8)	−0.0020 (6)	−0.0013 (6)	−0.0002 (6)
C5	0.0253 (8)	0.0260 (9)	0.0189 (8)	−0.0052 (7)	−0.0020 (6)	0.0010 (6)
C6	0.0329 (9)	0.0270 (9)	0.0261 (9)	−0.0101 (7)	−0.0040 (7)	0.0050 (7)
C7	0.0424 (11)	0.0204 (8)	0.0292 (9)	−0.0010 (7)	−0.0090 (8)	0.0015 (7)
C8	0.0348 (10)	0.0263 (9)	0.0255 (9)	0.0057 (7)	−0.0034 (7)	−0.0038 (7)
C9	0.0266 (8)	0.0259 (9)	0.0209 (8)	−0.0015 (7)	0.0011 (6)	−0.0003 (6)
C10	0.0220 (8)	0.0235 (8)	0.0184 (8)	0.0022 (6)	0.0043 (6)	−0.0017 (6)
C11	0.0203 (8)	0.0232 (8)	0.0212 (8)	0.0057 (6)	0.0025 (6)	−0.0006 (6)
C12	0.0237 (8)	0.0244 (8)	0.0256 (9)	0.0003 (7)	0.0011 (7)	−0.0044 (7)
C13	0.0350 (9)	0.0183 (8)	0.0261 (9)	0.0039 (7)	0.0045 (7)	−0.0016 (6)
C14	0.0290 (9)	0.0285 (9)	0.0225 (8)	0.0120 (7)	0.0007 (7)	0.0022 (7)
C15	0.0216 (8)	0.0306 (9)	0.0202 (8)	0.0021 (7)	0.0007 (6)	−0.0013 (7)
F1	0.0439 (7)	0.0325 (6)	0.0472 (7)	−0.0155 (5)	0.0033 (5)	0.0115 (5)
F2	0.0594 (8)	0.0186 (5)	0.0490 (7)	−0.0013 (5)	−0.0074 (6)	0.0034 (5)
F3	0.0461 (7)	0.0310 (6)	0.0403 (7)	0.0138 (5)	0.0032 (5)	−0.0063 (5)
F4	0.0301 (5)	0.0306 (5)	0.0288 (5)	0.0025 (4)	0.0112 (4)	0.0003 (4)
F5	0.0219 (5)	0.0231 (5)	0.0365 (6)	0.0045 (4)	−0.0039 (4)	0.0008 (4)
F6	0.0295 (6)	0.0246 (5)	0.0473 (7)	−0.0035 (4)	−0.0056 (5)	−0.0024 (5)
F7	0.0458 (7)	0.0190 (5)	0.0453 (7)	0.0035 (4)	0.0001 (5)	0.0011 (4)
F8	0.0386 (6)	0.0334 (6)	0.0400 (6)	0.0132 (5)	−0.0067 (5)	0.0068 (5)
F9	0.0249 (5)	0.0380 (6)	0.0369 (6)	0.0008 (4)	−0.0080 (4)	0.0023 (5)

Geometric parameters (Å, º)

O1—C4	1.3666 (19)	C8—F3	1.334 (2)
O1—C3	1.3679 (19)	C8—C9	1.371 (2)
O2—C1	1.220 (2)	C9—F4	1.3404 (19)
C1—C2	1.452 (2)	C10—C15	1.388 (2)
C1—C5	1.478 (2)	C10—C11	1.389 (2)
C2—C3	1.339 (2)	C11—F5	1.3474 (18)
C2—H2	0.9500	C11—C12	1.373 (2)
C3—C10	1.472 (2)	C12—F6	1.3404 (19)
C4—C9	1.385 (2)	C12—C13	1.383 (2)
C4—C5	1.401 (2)	C13—F7	1.3266 (19)
C5—C6	1.399 (2)	C13—C14	1.379 (2)
C6—F1	1.337 (2)	C14—F8	1.3343 (19)
C6—C7	1.371 (3)	C14—C15	1.380 (2)
C7—F2	1.334 (2)	C15—F9	1.3459 (19)
C7—C8	1.387 (3)
C4—O1—C3	118.08 (12)	F3—C8—C7	120.04 (16)
O2—C1—C2	122.66 (17)	C9—C8—C7	120.05 (17)
O2—C1—C5	123.48 (16)	F4—C9—C8	120.06 (15)
C2—C1—C5	113.86 (14)	F4—C9—C4	119.95 (14)
C3—C2—C1	122.57 (16)	C8—C9—C4	119.99 (16)
C3—C2—H2	118.7	C15—C10—C11	116.44 (15)
C1—C2—H2	118.7	C15—C10—C3	122.51 (15)
C2—C3—O1	123.20 (15)	C11—C10—C3	121.03 (14)
C2—C3—C10	125.37 (15)	F5—C11—C12	117.95 (14)
O1—C3—C10	111.41 (13)	F5—C11—C10	119.51 (14)
O1—C4—C9	115.44 (14)	C12—C11—C10	122.45 (15)
O1—C4—C5	123.26 (15)	F6—C12—C11	120.04 (15)
C9—C4—C5	121.29 (15)	F6—C12—C13	120.17 (15)
C6—C5—C4	116.99 (16)	C11—C12—C13	119.79 (16)
C6—C5—C1	124.03 (15)	F7—C13—C14	120.38 (15)
C4—C5—C1	118.97 (15)	F7—C13—C12	120.30 (16)
F1—C6—C7	117.74 (16)	C14—C13—C12	119.32 (16)
F1—C6—C5	120.50 (17)	F8—C14—C13	119.77 (16)
C7—C6—C5	121.74 (16)	F8—C14—C15	120.29 (16)
F2—C7—C6	120.51 (17)	C13—C14—C15	119.89 (15)
F2—C7—C8	119.58 (17)	F9—C15—C14	118.10 (15)
C6—C7—C8	119.90 (16)	F9—C15—C10	119.77 (15)
F3—C8—C9	119.91 (17)	C14—C15—C10	122.10 (15)
O2—C1—C2—C3	177.97 (16)	O1—C4—C9—F4	1.5 (2)
C5—C1—C2—C3	−1.7 (2)	C5—C4—C9—F4	−178.19 (15)
C1—C2—C3—O1	−0.2 (3)	O1—C4—C9—C8	−178.58 (15)
C1—C2—C3—C10	178.40 (15)	C5—C4—C9—C8	1.7 (3)
C4—O1—C3—C2	1.7 (2)	C2—C3—C10—C15	53.2 (2)
C4—O1—C3—C10	−177.04 (13)	O1—C3—C10—C15	−128.04 (16)
C3—O1—C4—C9	179.09 (14)	C2—C3—C10—C11	−124.98 (18)
C3—O1—C4—C5	−1.2 (2)	O1—C3—C10—C11	53.74 (19)
O1—C4—C5—C6	178.39 (14)	C15—C10—C11—F5	−175.78 (14)
C9—C4—C5—C6	−1.9 (2)	C3—C10—C11—F5	2.5 (2)
O1—C4—C5—C1	−0.8 (2)	C15—C10—C11—C12	0.8 (2)
C9—C4—C5—C1	178.92 (15)	C3—C10—C11—C12	179.10 (15)
O2—C1—C5—C6	3.3 (3)	F5—C11—C12—F6	−2.7 (2)
C2—C1—C5—C6	−176.97 (16)	C10—C11—C12—F6	−179.26 (15)
O2—C1—C5—C4	−177.56 (16)	F5—C11—C12—C13	176.28 (15)
C2—C1—C5—C4	2.2 (2)	C10—C11—C12—C13	−0.3 (3)
C4—C5—C6—F1	−177.89 (15)	F6—C12—C13—F7	−1.9 (2)
C1—C5—C6—F1	1.3 (3)	C11—C12—C13—F7	179.20 (15)
C4—C5—C6—C7	0.9 (3)	F6—C12—C13—C14	178.36 (15)
C1—C5—C6—C7	180.00 (16)	C11—C12—C13—C14	−0.6 (3)
F1—C6—C7—F2	−0.6 (3)	F7—C13—C14—F8	−1.4 (2)
C5—C6—C7—F2	−179.34 (15)	C12—C13—C14—F8	178.35 (15)
F1—C6—C7—C8	179.17 (15)	F7—C13—C14—C15	−178.79 (15)
C5—C6—C7—C8	0.4 (3)	C12—C13—C14—C15	1.0 (3)
F2—C7—C8—F3	−1.0 (2)	F8—C14—C15—F9	0.2 (2)
C6—C7—C8—F3	179.22 (16)	C13—C14—C15—F9	177.58 (15)
F2—C7—C8—C9	179.07 (16)	F8—C14—C15—C10	−177.87 (15)
C6—C7—C8—C9	−0.7 (3)	C13—C14—C15—C10	−0.5 (3)
F3—C8—C9—F4	−0.4 (3)	C11—C10—C15—F9	−178.43 (14)
C7—C8—C9—F4	179.51 (15)	C3—C10—C15—F9	3.3 (2)
F3—C8—C9—C4	179.75 (15)	C11—C10—C15—C14	−0.4 (2)
C7—C8—C9—C4	−0.4 (3)	C3—C10—C15—C14	−178.64 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···F5^i	0.95	2.42	3.3126 (19)	157

Symmetry code: (i) x+1, y, z.

(II) 5,6,7,8-tetrafluoro-2-phenyl-4H-1-benzopyran-4-one

Crystal data

C15H6F4O2	F(000) = 592
Mr = 294.20	Dx = 1.679 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1813 reflections
a = 7.5400 (11) Å	θ = 2.8–27.8°
b = 6.4742 (10) Å	µ = 0.15 mm^−1
c = 23.920 (4) Å	T = 100 K
β = 94.635 (2)°	Prismatic, pale yellow
V = 1163.9 (3) Å^3	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection

Bruker APEXII CCD area-detector diffractometer	2654 independent reflections
Radiation source: fine-focus sealed tube	1979 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
Detector resolution: 8.333 pixels mm^-1	θmax = 27.9°, θmin = 1.7°
ϕ and ω scans	h = −9→9
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	k = −8→5
Tmin = 0.955, Tmax = 0.985	l = −31→26
6192 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.094	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0373P)^2 + 0.4193P] where P = (Fo^2 + 2Fc^2)/3
2654 reflections	(Δ/σ)max = 0.001
238 parameters	Δρmax = 0.25 e Å^−3
57 restraints	Δρmin = −0.16 e Å^−3

Special details

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 > 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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1A	0.9015 (2)	0.2512 (3)	1.05707 (7)	0.0227 (4)	0.938 (2)
C2A	0.8533 (2)	0.2554 (3)	0.99739 (7)	0.0227 (4)	0.938 (2)
H2A	0.8876	0.1422	0.9754	0.027*	0.938 (2)
C3A	0.7625 (2)	0.4110 (3)	0.97134 (7)	0.0214 (4)	0.938 (2)
C4A	0.7530 (2)	0.5915 (3)	1.05683 (7)	0.0220 (4)	0.938 (2)
C5A	0.8444 (2)	0.4355 (3)	1.08735 (7)	0.0216 (4)	0.938 (2)
C6A	0.8793 (2)	0.4668 (3)	1.14526 (7)	0.0247 (4)	0.938 (2)
C7A	0.8271 (2)	0.6452 (3)	1.17037 (7)	0.0273 (4)	0.938 (2)
C8A	0.7384 (2)	0.7974 (3)	1.13874 (8)	0.0274 (4)	0.938 (2)
C9A	0.6996 (2)	0.7709 (3)	1.08234 (7)	0.0247 (4)	0.938 (2)
C10A	0.7074 (3)	0.4292 (3)	0.91119 (7)	0.0223 (4)	0.938 (2)
C11A	0.6345 (3)	0.6102 (3)	0.88843 (8)	0.0264 (4)	0.938 (2)
H11A	0.6195	0.7258	0.9120	0.032*	0.938 (2)
C12A	0.5831 (3)	0.6239 (3)	0.83139 (9)	0.0315 (4)	0.938 (2)
H12A	0.5338	0.7488	0.8162	0.038*	0.938 (2)
C13A	0.6037 (3)	0.4563 (4)	0.79684 (8)	0.0309 (5)	0.938 (2)
H13A	0.5676	0.4658	0.7579	0.037*	0.938 (2)
C14A	0.6769 (3)	0.2744 (3)	0.81867 (9)	0.0293 (5)	0.938 (2)
H14A	0.6912	0.1596	0.7947	0.035*	0.938 (2)
C15A	0.7295 (2)	0.2597 (3)	0.87568 (8)	0.0267 (4)	0.938 (2)
H15A	0.7804	0.1351	0.8906	0.032*	0.938 (2)
F1A	0.96454 (16)	0.32372 (19)	1.17779 (5)	0.0344 (3)	0.938 (2)
F2A	0.86160 (17)	0.6723 (2)	1.22578 (4)	0.0377 (3)	0.938 (2)
F3A	0.69073 (17)	0.97080 (19)	1.16361 (5)	0.0369 (3)	0.938 (2)
F4A	0.61061 (17)	0.91801 (18)	1.05211 (5)	0.0315 (3)	0.938 (2)
O1A	0.71037 (15)	0.58076 (18)	1.00029 (5)	0.0232 (3)	0.938 (2)
O2A	0.9843 (2)	0.1084 (2)	1.08037 (7)	0.0288 (3)	0.938 (2)
C1B	0.667 (4)	0.830 (3)	1.0454 (8)	0.030 (3)*	0.062 (2)
C2B	0.643 (3)	0.757 (3)	0.9885 (8)	0.030 (3)*	0.062 (2)
H2B	0.5796	0.8433	0.9618	0.036*	0.062 (2)
C3B	0.703 (4)	0.580 (3)	0.9704 (7)	0.030 (3)*	0.062 (2)
C4B	0.8116 (16)	0.4950 (19)	1.0635 (4)	0.030 (3)*	0.062 (2)
C5B	0.759 (3)	0.681 (2)	1.0859 (5)	0.030 (3)*	0.062 (2)
C6B	0.792 (3)	0.719 (3)	1.1430 (5)	0.030 (3)*	0.062 (2)
C7B	0.877 (2)	0.571 (3)	1.1777 (4)	0.030 (3)*	0.062 (2)
C8B	0.929 (3)	0.385 (3)	1.1552 (5)	0.030 (3)*	0.062 (2)
C9B	0.897 (3)	0.347 (2)	1.0981 (5)	0.030 (3)*	0.062 (2)
C10B	0.688 (3)	0.497 (3)	0.9101 (4)	0.030 (3)*	0.062 (2)
C11B	0.740 (3)	0.335 (3)	0.9042 (5)	0.030 (3)*	0.062 (2)
H11B	0.7858	0.2649	0.9372	0.036*	0.062 (2)
C12B	0.743 (5)	0.222 (4)	0.8524 (10)	0.030 (3)*	0.062 (2)
H12B	0.7891	0.0865	0.8497	0.036*	0.062 (2)
C13B	0.672 (6)	0.336 (5)	0.8071 (12)	0.030 (3)*	0.062 (2)
H13B	0.6754	0.2806	0.7704	0.036*	0.062 (2)
C14B	0.595 (5)	0.526 (6)	0.8135 (11)	0.030 (3)*	0.062 (2)
H14B	0.5324	0.5926	0.7825	0.036*	0.062 (2)
C15B	0.611 (5)	0.621 (5)	0.8660 (11)	0.030 (3)*	0.062 (2)
H15B	0.5732	0.7586	0.8717	0.036*	0.062 (2)
F1B	0.753 (4)	0.889 (4)	1.1709 (11)	0.078 (6)*	0.062 (2)
F2B	0.918 (4)	0.575 (4)	1.2335 (7)	0.078 (6)*	0.062 (2)
F3B	1.016 (4)	0.234 (4)	1.1855 (10)	0.078 (6)*	0.062 (2)
F4B	0.952 (6)	0.165 (5)	1.0780 (16)	0.078 (6)*	0.062 (2)
O1B	0.783 (2)	0.442 (3)	1.0078 (6)	0.030 (3)*	0.062 (2)
O2B	0.602 (6)	0.989 (5)	1.0642 (15)	0.078 (6)*	0.062 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0189 (9)	0.0217 (9)	0.0273 (10)	−0.0016 (7)	0.0015 (7)	0.0002 (8)
C2A	0.0235 (9)	0.0196 (8)	0.0253 (9)	−0.0001 (7)	0.0026 (7)	−0.0032 (7)
C3A	0.0183 (8)	0.0213 (9)	0.0252 (9)	−0.0028 (7)	0.0046 (7)	−0.0021 (7)
C4A	0.0194 (8)	0.0216 (9)	0.0254 (9)	−0.0032 (7)	0.0047 (7)	−0.0007 (7)
C5A	0.0182 (8)	0.0223 (9)	0.0248 (9)	−0.0029 (7)	0.0042 (7)	0.0000 (7)
C6A	0.0210 (9)	0.0266 (10)	0.0266 (9)	−0.0025 (7)	0.0019 (7)	0.0041 (8)
C7A	0.0275 (10)	0.0315 (10)	0.0231 (9)	−0.0077 (8)	0.0026 (7)	−0.0035 (8)
C8A	0.0270 (10)	0.0229 (10)	0.0333 (10)	−0.0037 (8)	0.0094 (8)	−0.0062 (8)
C9A	0.0222 (9)	0.0218 (9)	0.0303 (10)	−0.0015 (7)	0.0039 (7)	0.0006 (8)
C10A	0.0171 (8)	0.0225 (10)	0.0274 (9)	−0.0008 (7)	0.0023 (7)	0.0005 (7)
C11A	0.0252 (10)	0.0246 (9)	0.0288 (10)	−0.0005 (8)	−0.0012 (9)	0.0017 (9)
C12A	0.0318 (10)	0.0305 (11)	0.0314 (11)	0.0010 (9)	−0.0032 (9)	0.0074 (9)
C13A	0.0290 (10)	0.0395 (14)	0.0240 (10)	−0.0013 (10)	0.0011 (8)	0.0028 (9)
C14A	0.0280 (10)	0.0336 (12)	0.0266 (11)	−0.0002 (11)	0.0047 (10)	−0.0038 (9)
C15A	0.0232 (9)	0.0264 (10)	0.0308 (11)	0.0034 (8)	0.0048 (8)	0.0002 (8)
F1A	0.0384 (7)	0.0349 (7)	0.0290 (6)	0.0033 (6)	−0.0025 (5)	0.0035 (5)
F2A	0.0477 (8)	0.0426 (7)	0.0226 (6)	−0.0054 (6)	0.0012 (5)	−0.0085 (5)
F3A	0.0446 (8)	0.0283 (6)	0.0389 (7)	−0.0027 (5)	0.0102 (5)	−0.0121 (5)
F4A	0.0348 (6)	0.0227 (7)	0.0371 (7)	0.0048 (5)	0.0041 (5)	0.0005 (5)
O1A	0.0245 (6)	0.0206 (6)	0.0244 (7)	0.0032 (5)	0.0012 (5)	0.0001 (5)
O2A	0.0308 (9)	0.0273 (8)	0.0277 (7)	0.0047 (6)	−0.0014 (6)	0.0017 (6)

Geometric parameters (Å, º)

C1A—O2A	1.224 (2)	C1B—O2B	1.241 (18)
C1A—C2A	1.445 (2)	C1B—C2B	1.438 (17)
C1A—C5A	1.478 (2)	C1B—C5B	1.497 (16)
C2A—C3A	1.342 (2)	C2B—C3B	1.316 (17)
C2A—H2A	0.9500	C2B—H2B	0.9500
C3A—O1A	1.373 (2)	C3B—O1B	1.370 (17)
C3A—C10A	1.470 (2)	C3B—C10B	1.534 (15)
C4A—O1A	1.366 (2)	C4B—O1B	1.373 (14)
C4A—C9A	1.387 (2)	C4B—C5B	1.3900
C4A—C5A	1.395 (2)	C4B—C9B	1.3900
C5A—C6A	1.404 (2)	C5B—C6B	1.3900
C6A—F1A	1.340 (2)	C6B—F1B	1.333 (17)
C6A—C7A	1.374 (3)	C6B—C7B	1.3900
C7A—F2A	1.341 (2)	C7B—F2B	1.346 (16)
C7A—C8A	1.382 (3)	C7B—C8B	1.3900
C8A—F3A	1.334 (2)	C8B—F3B	1.352 (16)
C8A—C9A	1.368 (3)	C8B—C9B	1.3900
C9A—F4A	1.342 (2)	C9B—F4B	1.352 (17)
C10A—C11A	1.387 (3)	C10B—C11B	1.1373
C10A—C15A	1.406 (3)	C10B—C15B	1.409 (17)
C11A—C12A	1.391 (3)	C11B—C12B	1.438 (18)
C11A—H11A	0.9500	C11B—H11B	0.9500
C12A—C13A	1.380 (3)	C12B—C13B	1.383 (19)
C12A—H12A	0.9500	C12B—H12B	0.9500
C13A—C14A	1.385 (3)	C13B—C14B	1.374 (19)
C13A—H13A	0.9500	C13B—H13B	0.9500
C14A—C15A	1.392 (3)	C14B—C15B	1.395 (19)
C14A—H14A	0.9500	C14B—H14B	0.9500
C15A—H15A	0.9500	C15B—H15B	0.9500
O2A—C1A—C2A	122.87 (16)	O2B—C1B—C2B	126 (2)
O2A—C1A—C5A	122.99 (17)	O2B—C1B—C5B	118 (2)
C2A—C1A—C5A	114.13 (16)	C2B—C1B—C5B	114.7 (15)
C3A—C2A—C1A	123.44 (16)	C3B—C2B—C1B	125.2 (18)
C3A—C2A—H2A	118.3	C3B—C2B—H2B	117.4
C1A—C2A—H2A	118.3	C1B—C2B—H2B	117.4
C2A—C3A—O1A	121.50 (16)	C2B—C3B—O1B	119.8 (15)
C2A—C3A—C10A	127.42 (16)	C2B—C3B—C10B	127.6 (16)
O1A—C3A—C10A	111.08 (14)	O1B—C3B—C10B	112.5 (13)
O1A—C4A—C9A	115.13 (15)	O1B—C4B—C5B	124.3 (9)
O1A—C4A—C5A	123.22 (15)	O1B—C4B—C9B	115.7 (9)
C9A—C4A—C5A	121.65 (16)	C5B—C4B—C9B	120.0
C4A—C5A—C6A	117.23 (16)	C6B—C5B—C4B	120.0
C4A—C5A—C1A	118.63 (16)	C6B—C5B—C1B	124.0 (8)
C6A—C5A—C1A	124.13 (16)	C4B—C5B—C1B	116.0 (8)
F1A—C6A—C7A	117.90 (16)	F1B—C6B—C5B	127.5 (13)
F1A—C6A—C5A	121.11 (16)	F1B—C6B—C7B	112.5 (14)
C7A—C6A—C5A	120.99 (16)	C5B—C6B—C7B	120.0
F2A—C7A—C6A	120.15 (17)	F2B—C7B—C8B	110.6 (13)
F2A—C7A—C8A	119.64 (17)	F2B—C7B—C6B	129.4 (13)
C6A—C7A—C8A	120.20 (17)	C8B—C7B—C6B	120.0
F3A—C8A—C9A	120.11 (17)	F3B—C8B—C9B	116.0 (13)
F3A—C8A—C7A	119.46 (17)	F3B—C8B—C7B	124.0 (13)
C9A—C8A—C7A	120.43 (17)	C9B—C8B—C7B	120.0
F4A—C9A—C8A	120.02 (16)	F4B—C9B—C8B	117.9 (16)
F4A—C9A—C4A	120.50 (16)	F4B—C9B—C4B	122.1 (16)
C8A—C9A—C4A	119.48 (16)	C8B—C9B—C4B	120.0
C11A—C10A—C15A	119.01 (17)	C11B—C10B—C15B	123.9 (14)
C11A—C10A—C3A	121.58 (17)	C11B—C10B—C3B	116.0 (8)
C15A—C10A—C3A	119.41 (17)	C15B—C10B—C3B	120.1 (17)
C10A—C11A—C12A	120.62 (19)	C10B—C11B—C12B	127.2 (15)
C10A—C11A—H11A	119.7	C10B—C11B—H11B	116.4
C12A—C11A—H11A	119.7	C12B—C11B—H11B	116.4
C13A—C12A—C11A	120.08 (18)	C13B—C12B—C11B	112 (2)
C13A—C12A—H12A	120.0	C13B—C12B—H12B	124.0
C11A—C12A—H12A	120.0	C11B—C12B—H12B	124.0
C12A—C13A—C14A	120.22 (18)	C14B—C13B—C12B	122 (2)
C12A—C13A—H13A	119.9	C14B—C13B—H13B	119.0
C14A—C13A—H13A	119.9	C12B—C13B—H13B	119.0
C13A—C14A—C15A	120.1 (2)	C13B—C14B—C15B	119 (2)
C13A—C14A—H14A	120.0	C13B—C14B—H14B	120.4
C15A—C14A—H14A	120.0	C15B—C14B—H14B	120.4
C14A—C15A—C10A	119.99 (19)	C14B—C15B—C10B	115.2 (19)
C14A—C15A—H15A	120.0	C14B—C15B—H15B	122.4
C10A—C15A—H15A	120.0	C10B—C15B—H15B	122.4
C4A—O1A—C3A	119.06 (13)	C3B—O1B—C4B	119.8 (14)
O2A—C1A—C2A—C3A	−179.99 (18)	O2B—C1B—C2B—C3B	−175 (4)
C5A—C1A—C2A—C3A	−0.9 (2)	C5B—C1B—C2B—C3B	−4 (5)
C1A—C2A—C3A—O1A	0.8 (3)	C1B—C2B—C3B—O1B	5 (5)
C1A—C2A—C3A—C10A	−179.91 (17)	C1B—C2B—C3B—C10B	−177 (3)
O1A—C4A—C5A—C6A	−179.94 (16)	O1B—C4B—C5B—C6B	179.1 (12)
C9A—C4A—C5A—C6A	0.4 (2)	C9B—C4B—C5B—C6B	0.0
O1A—C4A—C5A—C1A	1.3 (2)	O1B—C4B—C5B—C1B	0 (2)
C9A—C4A—C5A—C1A	−178.33 (16)	C9B—C4B—C5B—C1B	−180 (2)
O2A—C1A—C5A—C4A	178.99 (17)	O2B—C1B—C5B—C6B	−7 (4)
C2A—C1A—C5A—C4A	−0.1 (2)	C2B—C1B—C5B—C6B	−178.4 (18)
O2A—C1A—C5A—C6A	0.3 (3)	O2B—C1B—C5B—C4B	173 (3)
C2A—C1A—C5A—C6A	−178.82 (16)	C2B—C1B—C5B—C4B	1 (3)
C4A—C5A—C6A—F1A	179.20 (15)	C4B—C5B—C6B—F1B	179 (3)
C1A—C5A—C6A—F1A	−2.1 (3)	C1B—C5B—C6B—F1B	−2 (2)
C4A—C5A—C6A—C7A	−0.8 (2)	C4B—C5B—C6B—C7B	0.0
C1A—C5A—C6A—C7A	177.92 (16)	C1B—C5B—C6B—C7B	180 (2)
F1A—C6A—C7A—F2A	0.0 (3)	F1B—C6B—C7B—F2B	2 (3)
C5A—C6A—C7A—F2A	179.99 (16)	C5B—C6B—C7B—F2B	−179 (2)
F1A—C6A—C7A—C8A	−179.83 (16)	F1B—C6B—C7B—C8B	−179 (2)
C5A—C6A—C7A—C8A	0.1 (3)	C5B—C6B—C7B—C8B	0.0
F2A—C7A—C8A—F3A	1.1 (3)	F2B—C7B—C8B—F3B	−3 (3)
C6A—C7A—C8A—F3A	−179.07 (16)	C6B—C7B—C8B—F3B	178 (3)
F2A—C7A—C8A—C9A	−178.98 (16)	F2B—C7B—C8B—C9B	178.9 (17)
C6A—C7A—C8A—C9A	0.9 (3)	C6B—C7B—C8B—C9B	0.0
F3A—C8A—C9A—F4A	−1.2 (3)	F3B—C8B—C9B—F4B	1 (3)
C7A—C8A—C9A—F4A	178.82 (16)	C7B—C8B—C9B—F4B	179 (3)
F3A—C8A—C9A—C4A	178.74 (15)	F3B—C8B—C9B—C4B	−179 (2)
C7A—C8A—C9A—C4A	−1.2 (3)	C7B—C8B—C9B—C4B	0.0
O1A—C4A—C9A—F4A	0.9 (2)	O1B—C4B—C9B—F4B	2 (3)
C5A—C4A—C9A—F4A	−179.48 (15)	C5B—C4B—C9B—F4B	−179 (3)
O1A—C4A—C9A—C8A	−179.11 (15)	O1B—C4B—C9B—C8B	−179.2 (11)
C5A—C4A—C9A—C8A	0.5 (3)	C5B—C4B—C9B—C8B	0.0
C2A—C3A—C10A—C11A	−171.40 (18)	C2B—C3B—C10B—C11B	−176 (3)
O1A—C3A—C10A—C11A	8.0 (2)	O1B—C3B—C10B—C11B	2 (3)
C2A—C3A—C10A—C15A	8.3 (3)	C2B—C3B—C10B—C15B	4 (5)
O1A—C3A—C10A—C15A	−172.29 (16)	O1B—C3B—C10B—C15B	−179 (3)
C15A—C10A—C11A—C12A	0.3 (3)	C15B—C10B—C11B—C12B	2 (3)
C3A—C10A—C11A—C12A	−179.96 (17)	C3B—C10B—C11B—C12B	−179 (3)
C10A—C11A—C12A—C13A	0.3 (3)	C10B—C11B—C12B—C13B	−1 (4)
C11A—C12A—C13A—C14A	−0.5 (3)	C11B—C12B—C13B—C14B	−5 (6)
C12A—C13A—C14A—C15A	0.2 (3)	C12B—C13B—C14B—C15B	9 (7)
C13A—C14A—C15A—C10A	0.4 (3)	C13B—C14B—C15B—C10B	−8 (6)
C11A—C10A—C15A—C14A	−0.6 (3)	C11B—C10B—C15B—C14B	3 (5)
C3A—C10A—C15A—C14A	179.63 (18)	C3B—C10B—C15B—C14B	−177 (3)
C9A—C4A—O1A—C3A	178.19 (14)	C2B—C3B—O1B—C4B	−4 (4)
C5A—C4A—O1A—C3A	−1.5 (2)	C10B—C3B—O1B—C4B	178 (2)
C2A—C3A—O1A—C4A	0.4 (2)	C5B—C4B—O1B—C3B	2 (3)
C10A—C3A—O1A—C4A	−179.02 (14)	C9B—C4B—O1B—C3B	−179 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12A—H12A···F2A^i	0.95	2.48	3.198 (2)	132

Symmetry code: (i) x−1/2, −y+3/2, z−1/2.