Crystal structure of 3-(tri-phenyl-phosphoranyl-idene)-2,5-di-hydro-furan-2,5-dione tetra-hydro-furan monosolvate.

The title pseudo-polymorph of 3-(tri-phenyl-phospho-ranyl-idene)-2,5-di-hydro-furan-2,5-dione crystallizes with a tetra-hydro-furan solvent mol-ecule, viz. C22H17O3P·C4H8O. The succinic anhydride ring is approximately planar (r.m.s. deviation = 0.032 Å). The tetra-hydro-furan mol-ecule is disordered over two orientations about a pseudo-twofold axis with refined occupancy ratio 0.718 (4):0.282 (4). In the crystal, C-H⋯O hydrogen bonds link mol-ecules of the di-hydro-furan-2,5-dione derivative into chains parallel to the b axis and arranged into layers stacked along [100] alternating with hydrogen-bonded tetra-hydro-furan layers.

Chemical context

Pseudopolymorphs are solvated forms of a compound that have different crystal structures and/or differ in the nature of the included solvent (Kumar et al., 1999 ▸). The investigation of this phenomenon plays an important role for both fundamental and applied reasons. Phospho­rus ylides are useful inter­mediates, which have been used in many reactions and are involved in the synthesis of organic compounds (Selva et al., 2014 ▸; Kolodiazhnyi, 1999 ▸; Balema et al., 2002 ▸). In this paper, the structure of the pseudopolymorph of 3-(tri­phenyl­phospho­ranyl­idene)-2,5-di­hydro­furan-2,5-dione (Geoffroy et al., 1993 ▸), crystallized with a THF solvent mol­ecule, is described.

Structural commentary

In the title compound (Fig. 1 ▸), the succinic anhydride ring is almost planar (r.m.s. deviation = 0.032 Å), with the C4 methyl­enic carbon atom displaced by only 0.118 (2) Å out of the least-squares mean plane through atoms C1, C2, C3 and O1 [maximum deviation of 0.007 (2) Å for C2]. The phospho­rus atom deviates from the least-squares mean plane of the succinic anhydride ring by 0.1855 (4) Å. The arrangement of the phenyl rings is propeller-wise, which is common arrangement for Ph3P-X fragments. The THF solvent mol­ecule is disordered over two orientations related by a pseudo-twofold axis. As recently reported by Islamov et al. (2017 ▸), mol­ecules located in general positions rotate more easily than those located on symmetry elements, and the presence of disorder increases the number of minima on the profile of the rotational barrier, making the barrier even lower (Karlen et al., 2010 ▸). However, since the quality of the anisotropic displace­ment parameters of the THF atoms is low, an attempt to determine the height of the rotational barrier using TLS analysis (Dunitz et al., 1988 ▸) was unsuccessful.

Figure 1

The mol­ecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. Only the major component of the disordered THF mol­ecule is shown.

Supra­molecular features

In the crystal, 3-(tri­phenyl­phospho­ranyl­idene)-2,5-di­hydro­furan-2,5-dione mol­ecules inter­act through C—H⋯O hydrogen bonds (Table 1 ▸), forming chains running parallel to the b axis. Alternating layers of chains and THF mol­ecules are stacked parallel to the bc plane (Fig. 2 ▸) and connected by C—H⋯O hydrogen bonds (Table 1 ▸).

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O4F i	0.92 (2)	2.59 (2)	3.253 (8)	129.4 (18)
C22—H22⋯O2ii	0.95 (2)	2.55 (2)	3.386 (2)	148.2 (16)
C20—H20⋯O4	1.00 (3)	2.58 (2)	3.452 (4)	145.8 (19)
C21—H21⋯O4F iii	0.94 (2)	2.43 (2)	3.283 (6)	151 (2)

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

Figure 2

Crystal packing of the title compound viewed along the b axis.

Database survey

A search of the Cambridge Structural Database (Version 5.39, update February 2018; Groom et al., 2016 ▸) revealed 426 structures containing the Ph3P=C fragment. The distribution histogram of the P=C distance [with a mean value of 1.729 Å and a standard deviation of 0.030 Å] is shown in Fig. 3 ▸. The P=C distance in the title compound is 1.717 (2) Å, which in good agreement with that of the di­chloro­methane pseudopolymorph [1.717 (6) Å; Geoffroy et al., 1993 ▸]. In spite of the differences in the crystal packing, the conformation of the mol­ecule is very similar to that of the CH2Cl2 solvate (r.m.s. deviation = 0.032 Å; Fig. 4 ▸).

Figure 3

Distribution histogram of the P=C distance in Ph3P=C fragments.

Figure 4

Structure overlay of THF solvate (green) and CH2Cl2 solvate (blue; Geoffroy et al., 1993 ▸).

Synthesis and crystallization

To a stirred solution maleic anhydride (0.17 g, 1.72 mmol) in tetra­hydro­furan THF (5 mL) was added tri­phenyl­phosphine (0.45 g, 1.72 mmol) at room temperature. The reaction mixture was stirred at room temperature for 24 h, then the solution was filtered and concentrated under reduced pressure. The reaction mixture was allowed to cool in the freezer (243 K, three days) and yellowish crystals precipitated. The crystals were separated from solvent and dried to give 0.56 g (90%) of the title compound. 1H NMR (CDCl3, δ, ppm, J, Hz): 1.78 (m, CH2 from THF), 3.14 (s, 2H, CH2), 3.67 (m, OCH2 from THF), 7.44–7.72 (m, 15H, Ph). 31P{1H} NMR (CDCl3, δ, ppm, J, Hz): +13.6 (s).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. The THF mol­ecule is disordered over two sites with an occupancy ratio of 0.718 (4):0.282 (4). EADP and SAME restraints were used to model this disordered mol­ecule. The H atoms of the 3-(tri­phenyl­phosphor­anyl­idene) di­hydro­furan-2,5-dione mol­ecule were located in difference-Fourier maps and refined freely. The THF H atoms were placed geometrically and refined using a riding-model approximation with C—H = 0.99 Å, and with U iso(H) = 1.2U eq(C).

Table 2

Experimental details

Crystal data
Chemical formula	C22H17O3P·C4H8O
M r	432.43
Crystal system, space group	Monoclinic, P21/c
Temperature (K)	130
a, b, c (Å)	12.1287 (5), 10.5530 (4), 17.5838 (8)
β (°)	104.435 (4)
V (Å3)	2179.57 (16)
Z	4
Radiation type	Mo Kα
μ (mm−1)	0.16
Crystal size (mm)	0.20 × 0.15 × 0.05
Data collection
Diffractometer	Agilent Xcalibur Sapphire3 CCD
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2014 ▸)
T min, T max	0.995, 1
No. of measured, independent and observed [I > 2σ(I)] reflections	30663, 7381, 5123
R int	0.061
(sin θ/λ)max (Å−1)	0.758
Refinement
R[F 2 > 2σ(F 2)], wR(F 2), S	0.062, 0.130, 1.03
No. of reflections	7381
No. of parameters	370
No. of restraints	10
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)	0.55, −0.39

Computer programs: CrysAlis PRO (Agilent, 2014 ▸), SHELXS97 (Sheldrick, 2015a ▸), SHELXL2014 (Sheldrick, 2015b ▸), Mercury (Macrae et al., 2008 ▸), publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989018011775/rz5234sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989018011775/rz5234Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989018011775/rz5234Isup3.cdx

CCDC reference: 1862873

Additional supporting information: crystallographic information; 3D view; checkCIF report

C22H17O3P·C4H8O	F(000) = 912
Mr = 432.43	Dx = 1.318 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.1287 (5) Å	Cell parameters from 5863 reflections
b = 10.5530 (4) Å	θ = 3.0–32.6°
c = 17.5838 (8) Å	µ = 0.16 mm−1
β = 104.435 (4)°	T = 130 K
V = 2179.57 (16) Å3	Needles, pale yellow
Z = 4	0.20 × 0.15 × 0.05 mm

Agilent Xcalibur Sapphire3 CCD diffractometer	5123 reflections with I > 2σ(I)
Radiation source: sealed x-ray tube	Rint = 0.061
ω scans	θmax = 32.6°, θmin = 3.0°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −18→17
Tmin = 0.995, Tmax = 1	k = −15→15
30663 measured reflections	l = −26→26
7381 independent reflections

Refinement on F2	10 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.062	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.130	w = 1/[σ2(Fo2) + (0.0367P)2 + 1.6405P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
7381 reflections	Δρmax = 0.55 e Å−3
370 parameters	Δρmin = −0.39 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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
P1	0.35862 (4)	0.49261 (4)	0.15957 (2)	0.01719 (10)
O1	0.20198 (11)	0.76108 (12)	0.01566 (8)	0.0267 (3)
O2	0.35896 (12)	0.79120 (13)	0.11583 (8)	0.0325 (3)
O3	0.05937 (12)	0.67737 (15)	−0.07627 (8)	0.0365 (4)
C1	0.26851 (14)	0.58651 (16)	0.09179 (10)	0.0196 (3)
C2	0.28856 (15)	0.71485 (17)	0.08280 (10)	0.0228 (4)
C3	0.13225 (15)	0.66384 (19)	−0.01654 (11)	0.0252 (4)
C4	0.16138 (15)	0.54664 (18)	0.03290 (11)	0.0223 (3)
C5	0.32090 (14)	0.33056 (16)	0.13491 (9)	0.0184 (3)
C6	0.39680 (15)	0.24576 (18)	0.11459 (10)	0.0223 (4)
C7	0.36203 (17)	0.12181 (18)	0.09439 (11)	0.0263 (4)
C8	0.25270 (17)	0.08421 (18)	0.09336 (11)	0.0272 (4)
C9	0.17691 (17)	0.16811 (18)	0.11337 (11)	0.0259 (4)
C10	0.21095 (15)	0.29100 (17)	0.13488 (11)	0.0224 (3)
C11	0.34766 (14)	0.51365 (17)	0.25923 (9)	0.0191 (3)
C12	0.30953 (17)	0.62921 (19)	0.28046 (11)	0.0259 (4)
C13	0.30127 (18)	0.6482 (2)	0.35722 (12)	0.0302 (4)
C14	0.33144 (17)	0.5526 (2)	0.41208 (11)	0.0293 (4)
C15	0.36981 (17)	0.4372 (2)	0.39104 (11)	0.0278 (4)
C16	0.37760 (15)	0.41676 (18)	0.31450 (11)	0.0237 (4)
C17	0.50533 (14)	0.51511 (16)	0.15815 (10)	0.0194 (3)
C18	0.53141 (16)	0.56868 (18)	0.09223 (11)	0.0241 (4)
C19	0.64382 (17)	0.5776 (2)	0.08833 (12)	0.0304 (4)
C20	0.73049 (16)	0.5328 (2)	0.14956 (12)	0.0303 (4)
C21	0.70505 (16)	0.4806 (2)	0.21537 (11)	0.0283 (4)
C22	0.59299 (15)	0.47212 (19)	0.22015 (11)	0.0247 (4)
H4A	0.1714 (16)	0.476 (2)	0.0002 (12)	0.023 (5)*
H4B	0.0986 (18)	0.530 (2)	0.0566 (12)	0.028 (6)*
H6	0.4736 (18)	0.273 (2)	0.1138 (12)	0.027 (5)*
H7	0.4134 (16)	0.064 (2)	0.0801 (12)	0.021 (5)*
H8	0.2294 (18)	0.001 (2)	0.0810 (12)	0.028 (6)*
H9	0.1041 (19)	0.142 (2)	0.1131 (13)	0.033 (6)*
H10	0.1598 (18)	0.349 (2)	0.1476 (13)	0.031 (6)*
H12	0.2872 (18)	0.696 (2)	0.2434 (13)	0.033 (6)*
H13	0.273 (2)	0.728 (2)	0.3708 (14)	0.044 (7)*
H14	0.3238 (19)	0.566 (2)	0.4650 (14)	0.036 (6)*
H15	0.3900 (19)	0.370 (2)	0.4293 (14)	0.035 (6)*
H16	0.4058 (18)	0.332 (2)	0.2995 (13)	0.033 (6)*
H18	0.4709 (18)	0.601 (2)	0.0507 (13)	0.032 (6)*
H19	0.6601 (19)	0.614 (2)	0.0407 (14)	0.039 (6)*
H20	0.811 (2)	0.539 (2)	0.1460 (14)	0.039 (6)*
H21	0.7635 (19)	0.451 (2)	0.2572 (14)	0.037 (6)*
O4	0.9797 (3)	0.6888 (3)	0.1470 (2)	0.0667 (10)	0.718 (4)
C23	0.9886 (4)	0.7506 (4)	0.2223 (2)	0.0567 (10)	0.718 (4)
H23A	0.9324	0.7145	0.2485	0.068*	0.718 (4)
H23B	1.0658	0.7385	0.2570	0.068*	0.718 (4)
C24	0.9665 (11)	0.8833 (6)	0.2065 (6)	0.0645 (14)	0.718 (4)
H24A	1.0263	0.9358	0.2408	0.077*	0.718 (4)
H24B	0.8917	0.9074	0.2153	0.077*	0.718 (4)
C25	0.9668 (12)	0.9006 (11)	0.1196 (4)	0.076 (2)	0.718 (4)
H25A	0.9144	0.9690	0.0946	0.092*	0.718 (4)
H25B	1.0442	0.9189	0.1136	0.092*	0.718 (4)
C26	0.9267 (7)	0.7765 (9)	0.0877 (3)	0.0600 (12)	0.718 (4)
H26A	0.8428	0.7709	0.0770	0.072*	0.718 (4)
H26B	0.9496	0.7601	0.0383	0.072*	0.718 (4)
O4F	1.0380 (5)	0.9389 (7)	0.1713 (4)	0.057 (2)	0.282 (4)
C23F	0.965 (3)	0.9030 (19)	0.2222 (17)	0.0645 (14)	0.282 (4)
H23C	0.8965	0.9582	0.2132	0.077*	0.282 (4)
H23D	1.0061	0.9077	0.2782	0.077*	0.282 (4)
C24F	0.9329 (11)	0.7719 (12)	0.1986 (6)	0.0567 (10)	0.282 (4)
H24C	0.8575	0.7504	0.2072	0.068*	0.282 (4)
H24D	0.9902	0.7114	0.2281	0.068*	0.282 (4)
C25F	0.930 (2)	0.771 (3)	0.1100 (8)	0.0600 (12)	0.282 (4)
H25C	0.9780	0.7024	0.0974	0.072*	0.282 (4)
H25D	0.8510	0.7605	0.0774	0.072*	0.282 (4)
C26F	0.975 (3)	0.894 (3)	0.0982 (12)	0.076 (2)	0.282 (4)
H26C	1.0239	0.8877	0.0612	0.092*	0.282 (4)
H26D	0.9116	0.9534	0.0759	0.092*	0.282 (4)
H22	0.5776 (17)	0.437 (2)	0.2658 (12)	0.026 (5)*

	U11	U22	U33	U12	U13	U23
P1	0.01787 (19)	0.0168 (2)	0.01680 (18)	0.00042 (16)	0.00412 (14)	−0.00023 (17)
O1	0.0279 (7)	0.0222 (7)	0.0280 (7)	0.0025 (5)	0.0034 (5)	0.0065 (5)
O2	0.0379 (8)	0.0195 (7)	0.0358 (8)	−0.0044 (6)	0.0013 (6)	−0.0017 (6)
O3	0.0282 (7)	0.0449 (9)	0.0310 (7)	0.0028 (6)	−0.0029 (6)	0.0112 (7)
C1	0.0203 (8)	0.0182 (8)	0.0191 (8)	0.0000 (6)	0.0027 (6)	0.0005 (6)
C2	0.0236 (8)	0.0212 (9)	0.0231 (8)	0.0020 (7)	0.0048 (7)	0.0006 (7)
C3	0.0203 (8)	0.0301 (10)	0.0254 (9)	0.0035 (7)	0.0061 (7)	0.0043 (8)
C4	0.0182 (8)	0.0238 (9)	0.0236 (8)	−0.0002 (7)	0.0024 (6)	0.0026 (7)
C5	0.0208 (8)	0.0170 (8)	0.0165 (7)	0.0008 (6)	0.0032 (6)	0.0013 (6)
C6	0.0224 (8)	0.0235 (9)	0.0204 (8)	0.0040 (7)	0.0041 (7)	0.0007 (7)
C7	0.0340 (10)	0.0213 (9)	0.0228 (9)	0.0082 (8)	0.0056 (7)	−0.0008 (7)
C8	0.0369 (10)	0.0159 (8)	0.0269 (9)	−0.0010 (8)	0.0043 (8)	0.0005 (7)
C9	0.0270 (9)	0.0205 (9)	0.0300 (9)	−0.0020 (7)	0.0066 (7)	0.0012 (7)
C10	0.0237 (8)	0.0183 (8)	0.0257 (9)	0.0017 (7)	0.0069 (7)	0.0010 (7)
C11	0.0190 (7)	0.0204 (8)	0.0186 (7)	−0.0006 (6)	0.0060 (6)	−0.0012 (6)
C12	0.0340 (10)	0.0216 (9)	0.0236 (9)	0.0040 (8)	0.0097 (7)	0.0020 (7)
C13	0.0427 (11)	0.0242 (10)	0.0281 (9)	0.0053 (8)	0.0170 (8)	−0.0012 (8)
C14	0.0375 (11)	0.0318 (10)	0.0218 (9)	0.0002 (8)	0.0135 (8)	0.0002 (8)
C15	0.0346 (10)	0.0272 (10)	0.0228 (9)	0.0023 (8)	0.0095 (8)	0.0037 (8)
C16	0.0269 (9)	0.0234 (9)	0.0221 (8)	0.0013 (7)	0.0082 (7)	0.0012 (7)
C17	0.0195 (7)	0.0201 (8)	0.0185 (7)	−0.0013 (6)	0.0047 (6)	−0.0016 (6)
C18	0.0237 (8)	0.0275 (9)	0.0217 (8)	0.0009 (7)	0.0069 (7)	0.0009 (7)
C19	0.0286 (10)	0.0383 (12)	0.0273 (10)	−0.0018 (8)	0.0125 (8)	0.0016 (9)
C20	0.0208 (9)	0.0387 (12)	0.0322 (10)	−0.0040 (8)	0.0084 (7)	−0.0051 (9)
C21	0.0208 (8)	0.0373 (11)	0.0246 (9)	0.0006 (8)	0.0014 (7)	−0.0034 (8)
C22	0.0238 (8)	0.0293 (10)	0.0206 (8)	−0.0004 (7)	0.0048 (7)	−0.0001 (7)
O4	0.079 (2)	0.0495 (17)	0.083 (2)	0.0060 (15)	0.0406 (17)	−0.0007 (16)
C23	0.059 (3)	0.069 (3)	0.039 (2)	0.002 (2)	0.0074 (19)	0.0047 (19)
C24	0.061 (2)	0.058 (3)	0.079 (5)	−0.004 (3)	0.027 (3)	−0.022 (3)
C25	0.050 (3)	0.061 (3)	0.113 (6)	−0.007 (2)	0.012 (5)	0.018 (4)
C26	0.0586 (19)	0.092 (3)	0.029 (3)	−0.0256 (19)	0.011 (3)	−0.001 (3)
O4F	0.051 (4)	0.076 (5)	0.037 (3)	−0.041 (3)	−0.004 (3)	0.012 (3)
C23F	0.061 (2)	0.058 (3)	0.079 (5)	−0.004 (3)	0.027 (3)	−0.022 (3)
C24F	0.059 (3)	0.069 (3)	0.039 (2)	0.002 (2)	0.0074 (19)	0.0047 (19)
C25F	0.0586 (19)	0.092 (3)	0.029 (3)	−0.0256 (19)	0.011 (3)	−0.001 (3)
C26F	0.050 (3)	0.061 (3)	0.113 (6)	−0.007 (2)	0.012 (5)	0.018 (4)

P1—C1	1.7168 (17)	C17—C22	1.395 (2)
P1—C5	1.7952 (18)	C18—C19	1.385 (3)
P1—C17	1.8016 (17)	C18—H18	0.96 (2)
P1—C11	1.8039 (17)	C19—C20	1.387 (3)
O1—C3	1.360 (2)	C19—H19	0.98 (2)
O1—C2	1.455 (2)	C20—C21	1.384 (3)
O2—C2	1.212 (2)	C20—H20	1.00 (2)
O3—C3	1.201 (2)	C21—C22	1.385 (3)
C1—C2	1.392 (2)	C21—H21	0.94 (2)
C1—C4	1.506 (2)	C22—H22	0.95 (2)
C3—C4	1.502 (3)	O4—C26	1.423 (8)
C4—H4A	0.97 (2)	O4—C23	1.455 (5)
C4—H4B	0.97 (2)	C23—C24	1.440 (9)
C5—C6	1.393 (2)	C23—H23A	0.9900
C5—C10	1.397 (2)	C23—H23B	0.9900
C6—C7	1.393 (3)	C24—C25	1.540 (10)
C6—H6	0.98 (2)	C24—H24A	0.9900
C7—C8	1.380 (3)	C24—H24B	0.9900
C7—H7	0.95 (2)	C25—C26	1.460 (7)
C8—C9	1.383 (3)	C25—H25A	0.9900
C8—H8	0.94 (2)	C25—H25B	0.9900
C9—C10	1.385 (3)	C26—H26A	0.9900
C9—H9	0.93 (2)	C26—H26B	0.9900
C10—H10	0.94 (2)	O4F—C26F	1.404 (19)
C11—C12	1.388 (3)	O4F—C23F	1.461 (17)
C11—C16	1.395 (2)	C23F—C24F	1.468 (15)
C12—C13	1.393 (3)	C23F—H23C	0.9900
C12—H12	0.95 (2)	C23F—H23D	0.9900
C13—C14	1.381 (3)	C24F—C25F	1.549 (14)
C13—H13	0.96 (3)	C24F—H24C	0.9900
C14—C15	1.386 (3)	C24F—H24D	0.9900
C14—H14	0.97 (2)	C25F—C26F	1.445 (15)
C15—C16	1.389 (3)	C25F—H25C	0.9900
C15—H15	0.97 (2)	C25F—H25D	0.9900
C16—H16	1.02 (2)	C26F—H26C	0.9900
C17—C18	1.395 (2)	C26F—H26D	0.9900
C1—P1—C5	107.60 (8)	C17—C18—H18	119.1 (13)
C1—P1—C17	111.98 (8)	C18—C19—C20	120.22 (18)
C5—P1—C17	108.38 (8)	C18—C19—H19	118.5 (13)
C1—P1—C11	114.52 (8)	C20—C19—H19	121.3 (13)
C5—P1—C11	106.01 (8)	C21—C20—C19	120.07 (18)
C17—P1—C11	108.03 (8)	C21—C20—H20	120.2 (14)
C3—O1—C2	109.44 (14)	C19—C20—H20	119.7 (14)
C2—C1—C4	109.82 (15)	C20—C21—C22	120.18 (18)
C2—C1—P1	122.78 (13)	C20—C21—H21	120.4 (14)
C4—C1—P1	127.38 (13)	C22—C21—H21	119.4 (14)
O2—C2—C1	135.62 (17)	C21—C22—C17	119.98 (17)
O2—C2—O1	116.47 (16)	C21—C22—H22	118.8 (12)
C1—C2—O1	107.90 (15)	C17—C22—H22	121.3 (12)
O3—C3—O1	121.34 (18)	C26—O4—C23	107.1 (4)
O3—C3—C4	128.29 (19)	C24—C23—O4	107.0 (5)
O1—C3—C4	110.37 (15)	C24—C23—H23A	110.3
C3—C4—C1	101.89 (15)	O4—C23—H23A	110.3
C3—C4—H4A	109.7 (12)	C24—C23—H23B	110.3
C1—C4—H4A	114.2 (12)	O4—C23—H23B	110.3
C3—C4—H4B	107.5 (13)	H23A—C23—H23B	108.6
C1—C4—H4B	113.0 (12)	C23—C24—C25	105.1 (6)
H4A—C4—H4B	110.0 (17)	C23—C24—H24A	110.7
C6—C5—C10	119.98 (16)	C25—C24—H24A	110.7
C6—C5—P1	121.94 (13)	C23—C24—H24B	110.7
C10—C5—P1	118.06 (13)	C25—C24—H24B	110.7
C5—C6—C7	119.43 (17)	H24A—C24—H24B	108.8
C5—C6—H6	120.6 (13)	C26—C25—C24	101.1 (6)
C7—C6—H6	120.0 (13)	C26—C25—H25A	111.6
C8—C7—C6	120.15 (18)	C24—C25—H25A	111.6
C8—C7—H7	120.1 (12)	C26—C25—H25B	111.6
C6—C7—H7	119.7 (12)	C24—C25—H25B	111.6
C7—C8—C9	120.65 (18)	H25A—C25—H25B	109.4
C7—C8—H8	120.5 (13)	O4—C26—C25	104.8 (7)
C9—C8—H8	118.8 (13)	O4—C26—H26A	110.8
C8—C9—C10	119.81 (18)	C25—C26—H26A	110.8
C8—C9—H9	120.0 (14)	O4—C26—H26B	110.8
C10—C9—H9	120.2 (14)	C25—C26—H26B	110.8
C9—C10—C5	119.96 (17)	H26A—C26—H26B	108.9
C9—C10—H10	120.4 (13)	C26F—O4F—C23F	101.3 (16)
C5—C10—H10	119.6 (13)	O4F—C23F—C24F	103.2 (12)
C12—C11—C16	120.19 (16)	O4F—C23F—H23C	111.1
C12—C11—P1	118.66 (14)	C24F—C23F—H23C	111.1
C16—C11—P1	121.14 (13)	O4F—C23F—H23D	111.1
C11—C12—C13	119.78 (18)	C24F—C23F—H23D	111.1
C11—C12—H12	121.6 (14)	H23C—C23F—H23D	109.1
C13—C12—H12	118.6 (14)	C23F—C24F—C25F	103.2 (14)
C14—C13—C12	120.07 (18)	C23F—C24F—H24C	111.1
C14—C13—H13	121.2 (15)	C25F—C24F—H24C	111.1
C12—C13—H13	118.7 (15)	C23F—C24F—H24D	111.1
C13—C14—C15	120.23 (18)	C25F—C24F—H24D	111.1
C13—C14—H14	119.8 (14)	H24C—C24F—H24D	109.1
C15—C14—H14	120.0 (14)	C26F—C25F—C24F	102.9 (14)
C14—C15—C16	120.24 (18)	C26F—C25F—H25C	111.2
C14—C15—H15	120.3 (14)	C24F—C25F—H25C	111.2
C16—C15—H15	119.5 (14)	C26F—C25F—H25D	111.2
C15—C16—C11	119.48 (17)	C24F—C25F—H25D	111.2
C15—C16—H16	119.8 (13)	H25C—C25F—H25D	109.1
C11—C16—H16	120.7 (13)	O4F—C26F—C25F	108.1 (17)
C18—C17—C22	119.64 (16)	O4F—C26F—H26C	110.1
C18—C17—P1	119.62 (13)	C25F—C26F—H26C	110.1
C22—C17—P1	120.61 (13)	O4F—C26F—H26D	110.1
C19—C18—C17	119.90 (17)	C25F—C26F—H26D	110.1
C19—C18—H18	121.0 (13)	H26C—C26F—H26D	108.4

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O4Fi	0.92 (2)	2.59 (2)	3.253 (8)	129.4 (18)
C22—H22···O2ii	0.95 (2)	2.55 (2)	3.386 (2)	148.2 (16)
C20—H20···O4	1.00 (3)	2.58 (2)	3.452 (4)	145.8 (19)
C21—H21···O4Fiii	0.94 (2)	2.43 (2)	3.283 (6)	151 (2)