Bis(acetyl­acetonato-κ²O,O′)[2,2′-methyl­enebis(4,6-xylenolato)-κ²O,O′]titanium(IV)

The title compound, [Ti(C₅H₇O₂)₂(C₁₇H₁₈O₂)], was synthesized by the reaction of Ti(acac)₂Cl₂ (acac = acetyl­acetonate) with one equivalent of the diol {[HOC₆H₂(Me)₂](μ-CH₂)[(Me)₂C₆H₂OH]} in the presence of sodium acetate. The coordination about the Ti atom is slightly distorted octa­hedral and the bis­phenoxo ligand adopts an `open book' conformation.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.040
• wR factor = 0.127
• Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.25 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.71 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1

Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Ti1         (4)       4.30

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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S1. Comment

Titanium complexes containing aryloxides with bulky substituents are of interest in homogeneous catalysis, particularly in relation to polymerization processes (Priya et al., 2004; Fokken et al.,1996; Groysman et al., 2003). When bulky phenolate ligands are employed instead of metallocenes better results were obtained in polymerization of olefins (Hanava et al., 2003). The utility of titanium aryloxides in catalytic reactions such as olefin polymerization, oxidation, epoxidation and carbon-carbon coupling reactions are well documented (Chuck et al., 2006). Here, we report the mixed ligand complex [(–OC(CH₃)CHC(CH₃)O–)₂Ti{(–OC₆H₂(Me)₂)(µ-CH₂) ((Me)₂C₆H₂O–)}].

The coordination about the titanium(IV) center is distorted octahedral (Table 1). The acetylacetonate ligands are planar within 0.01 Å but are not coplanar with the metal. Instead, the O1, O2, C1, C2, C3 plane makes a dihedral angle of 16.1 (2)° with the Ti1 O1 O2 plane while the corresponding angle for the other acetylacetonate ligand is 14.0 (1)°. The bisphenoxo ligand adopts a open book conformation with the dihedral angle between the two aromatic rings being 106.79 (8)°. The two Ti—O—C angles associated with this ligand differ significantly (Table 1). This is attributed to packing considerations since the rings containing C20 through C26 in two adjacent molecules are parallel, partially interleaved and separated by 3.74 Å while C12 and C13 in the other ring make contacts, respectively, with H8 (2.88 Å) and H10B (2.89 Å) in the molecule at x,-1 + y,z. The former interaction tends to open up the Ti—O6—C20 angle while the latter acts to decrease the Ti—O5—C11 angle.

Related literature

For related literature, see: Chuck et al. (2006); Fokken et al. (1996); Groysman et al. (2003); Hanava et al. (2003); Priya et al. (2004).

S2. Experimental

To a solution of Ti(acac)₂Cl₂ (0.225 g, 0.71 mmol) in CH₃CN (15 ml), a mixture of diol (0.181 g, 0.71 mmol) and sodium acetate (0.116 g, 1.42 mmol) in the same solvent (15 ml) was added dropwise at 300 K and the mixture was refluxed for 8 h. The reaction mixture was cooled to room temperature and filtered through celite. The filtrate was concentrated to a small volume (3 ml) and hexane was added (2 ml). Storage of the solution at 263 K yielded dark red blocks of the title compound (0.237 g, 67%; m.p.: 419–421 K). Analysis, calculated for C₂₇H₃₂O₆Ti: C 64.77, H 6.45; found: C 64.62, H 6.46%. Spectroscopic analysis: ¹H NMR (300 MHz, 298 K, CDCl₃, δ, p.p.m.): 7.12–7.26 (m, 4 H, phenyl), 5.95 (s, 1 H, CH, acac), 4.41 (s, 2 H, CH₂), 2.08 (m, 6 H, CH₃), 1.42 (s, 18 H, tert-butyl).

S3. Refinement

H atoms were placed in calculated positions (C—H = 0.95–0.98 Å) and included as riding contributions with isotropic displacement parameters 1.2–1.5 times those of the attached carbon atoms.

Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures

Fig. 1. Perspective view of the title compound. Displacement ellipsoids are drawn at the 50% level and H-atoms are drawn as spheres of arbitrary radius.

Bis(acetylacetonato-κ²O,O')[2,2'-methylenebis(4,6-xylenolato)-κ²O,O'] titanium(IV)

Crystal data

[Ti(C5H7O2)2(C17H18O2)]	Z = 2
Mr = 500.43	F(000) = 528
Triclinic, P1	Dx = 1.272 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3605 (9) Å	Cell parameters from 25 reflections
b = 9.3419 (7) Å	θ = 18.2–23.1°
c = 17.652 (1) Å	µ = 0.37 mm^−1
α = 92.472 (5)°	T = 298 K
β = 95.599 (7)°	Block, red
γ = 107.209 (7)°	0.46 × 0.40 × 0.26 mm
V = 1306.9 (2) Å^3

Data collection

Enraf–Nonius CAD-4 diffractometer	3123 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
Graphite monochromator	θmax = 25.1°, θmin = 2.3°
θ/2θ scans	h = 0→9
Absorption correction: empirical (using intensity measurements) ψ scans (North et al., 1968)	k = −11→10
Tmin = 0.850, Tmax = 0.911	l = −21→20
4973 measured reflections	2 standard reflections every 2 min
4628 independent reflections	intensity decay: <1%

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) = 0.127	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.063P)^2 + 0.4456P] where P = (Fo^2 + 2Fc^2)/3
4628 reflections	(Δ/σ)max = 0.001
314 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.34 e Å^−3

Special details

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. H-atoms were placed in calculated positions (C—H = 0.95 - 0.98 Å) and included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached carbon atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Ti1	0.83024 (6)	0.95224 (5)	0.68559 (3)	0.04474 (16)
O1	0.7004 (3)	0.8836 (2)	0.57985 (11)	0.0600 (5)
O2	1.0249 (2)	0.9282 (2)	0.63419 (10)	0.0541 (5)
O3	0.8816 (2)	1.1664 (2)	0.65189 (10)	0.0516 (5)
O4	0.6234 (2)	0.9907 (2)	0.71662 (11)	0.0531 (5)
O5	0.7537 (2)	0.7554 (2)	0.70880 (10)	0.0508 (5)
O6	0.9587 (2)	1.02024 (19)	0.77511 (10)	0.0476 (4)
C1	0.7354 (5)	0.8132 (4)	0.52428 (17)	0.0732 (10)
C2	0.5923 (6)	0.7500 (6)	0.4607 (2)	0.1285 (19)
H2A	0.5136	0.6618	0.4762	0.193*
H2B	0.6367	0.7243	0.4156	0.193*
H2C	0.5361	0.8241	0.4499	0.193*
C3	0.8900 (5)	0.7935 (5)	0.5200 (2)	0.0895 (12)
H3	0.9025	0.7357	0.4780	0.107*
C4	1.0287 (4)	0.8529 (4)	0.57311 (17)	0.0637 (8)
C5	1.1956 (5)	0.8313 (5)	0.5618 (2)	0.0929 (13)
H5A	1.2845	0.9137	0.5879	0.111*
H5B	1.2076	0.8273	0.5083	0.111*
H5C	1.2015	0.7390	0.5820	0.111*
C6	0.8209 (3)	1.2722 (3)	0.67020 (15)	0.0481 (6)
C7	0.9100 (4)	1.4253 (3)	0.64689 (19)	0.0692 (9)
H7A	1.0217	1.4601	0.6736	0.083*
H7B	0.8488	1.4937	0.6593	0.083*
H7C	0.9164	1.4201	0.5929	0.083*
C8	0.6801 (3)	1.2504 (3)	0.70863 (16)	0.0529 (7)
H8	0.6478	1.3342	0.7224	0.063*
C9	0.5848 (3)	1.1124 (3)	0.72778 (14)	0.0477 (6)
C10	0.4241 (4)	1.0942 (4)	0.76311 (19)	0.0669 (9)
H10A	0.3294	1.0519	0.7251	0.080*
H10B	0.4213	1.1906	0.7830	0.080*
H10C	0.4191	1.0286	0.8038	0.080*
C11	0.7272 (3)	0.6725 (3)	0.77042 (14)	0.0434 (6)
C12	0.5619 (3)	0.5910 (3)	0.78049 (16)	0.0507 (7)
C13	0.5362 (4)	0.5020 (3)	0.84165 (17)	0.0552 (7)
H13	0.4264	0.4485	0.8488	0.066*
C14	0.6676 (4)	0.4898 (3)	0.89250 (16)	0.0499 (6)
C15	0.8289 (3)	0.5727 (3)	0.88113 (15)	0.0466 (6)
H15	0.9186	0.5661	0.9149	0.056*
C16	0.8635 (3)	0.6658 (3)	0.82145 (14)	0.0414 (6)
C17	0.4165 (4)	0.6007 (4)	0.7242 (2)	0.0755 (10)
H17A	0.3135	0.5307	0.7356	0.113*
H17B	0.4368	0.5769	0.6733	0.113*
H17C	0.4074	0.7008	0.7282	0.113*
C18	0.6375 (5)	0.3883 (4)	0.9572 (2)	0.0732 (9)
H18A	0.7436	0.3836	0.9814	0.088*
H18B	0.5694	0.2893	0.9376	0.088*
H18C	0.5804	0.4274	0.9938	0.088*
C19	1.0431 (3)	0.7572 (3)	0.81441 (15)	0.0432 (6)
H19A	1.0531	0.7811	0.7618	0.052*
H19B	1.1177	0.6977	0.8278	0.052*
C20	1.0499 (3)	1.0264 (3)	0.84343 (13)	0.0397 (5)
C21	1.0956 (3)	1.1597 (3)	0.89035 (15)	0.0439 (6)
C22	1.1872 (3)	1.1633 (3)	0.96104 (15)	0.0480 (6)
H22	1.2159	1.2506	0.9933	0.058*
C23	1.2369 (3)	1.0433 (3)	0.98512 (14)	0.0470 (6)
C24	1.1904 (3)	0.9132 (3)	0.93643 (15)	0.0448 (6)
H24	1.2227	0.8309	0.9519	0.054*
C25	1.0974 (3)	0.9015 (3)	0.86565 (14)	0.0399 (5)
C26	1.0431 (4)	1.2922 (3)	0.86477 (19)	0.0668 (9)
H26A	1.0880	1.3752	0.9026	0.080*
H26B	0.9223	1.2659	0.8582	0.080*
H26C	1.0855	1.3202	0.8172	0.080*
C27	1.3356 (4)	1.0516 (4)	1.06257 (16)	0.0612 (8)
H27A	1.3620	1.1512	1.0867	0.073*
H27B	1.4381	1.0282	1.0565	0.073*
H27C	1.2693	0.9807	1.0937	0.073*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ti1	0.0526 (3)	0.0502 (3)	0.0340 (3)	0.0202 (2)	0.00336 (19)	0.00056 (19)
O1	0.0672 (13)	0.0742 (14)	0.0399 (11)	0.0279 (11)	−0.0059 (9)	0.0002 (10)
O2	0.0589 (12)	0.0664 (12)	0.0435 (11)	0.0275 (10)	0.0117 (9)	0.0018 (9)
O3	0.0589 (12)	0.0553 (11)	0.0485 (11)	0.0248 (9)	0.0173 (9)	0.0113 (9)
O4	0.0501 (11)	0.0556 (11)	0.0554 (12)	0.0167 (9)	0.0127 (9)	0.0044 (9)
O5	0.0581 (11)	0.0503 (11)	0.0426 (10)	0.0164 (9)	−0.0002 (8)	0.0008 (8)
O6	0.0576 (11)	0.0481 (10)	0.0382 (10)	0.0195 (9)	0.0016 (8)	−0.0011 (8)
C1	0.097 (3)	0.085 (2)	0.0383 (17)	0.036 (2)	−0.0102 (16)	−0.0087 (16)
C2	0.140 (4)	0.160 (5)	0.075 (3)	0.055 (4)	−0.043 (3)	−0.050 (3)
C3	0.111 (3)	0.123 (3)	0.0485 (19)	0.062 (3)	0.0014 (19)	−0.024 (2)
C4	0.083 (2)	0.074 (2)	0.0461 (17)	0.0388 (18)	0.0187 (16)	0.0100 (15)
C5	0.102 (3)	0.126 (3)	0.075 (2)	0.065 (3)	0.031 (2)	0.004 (2)
C6	0.0546 (16)	0.0529 (16)	0.0370 (14)	0.0190 (13)	−0.0016 (11)	0.0021 (11)
C7	0.082 (2)	0.0534 (18)	0.072 (2)	0.0177 (16)	0.0174 (18)	0.0075 (15)
C8	0.0530 (16)	0.0559 (17)	0.0537 (17)	0.0238 (14)	0.0055 (13)	−0.0030 (13)
C9	0.0443 (15)	0.0617 (17)	0.0366 (14)	0.0184 (13)	−0.0010 (11)	−0.0065 (12)
C10	0.0517 (18)	0.082 (2)	0.069 (2)	0.0227 (16)	0.0139 (15)	−0.0076 (17)
C11	0.0513 (15)	0.0360 (13)	0.0438 (14)	0.0165 (12)	0.0031 (12)	−0.0059 (11)
C12	0.0463 (15)	0.0465 (15)	0.0566 (17)	0.0128 (12)	0.0025 (12)	−0.0093 (13)
C13	0.0477 (16)	0.0434 (15)	0.070 (2)	0.0061 (12)	0.0136 (14)	−0.0020 (14)
C14	0.0574 (17)	0.0361 (13)	0.0533 (16)	0.0089 (12)	0.0107 (13)	−0.0006 (12)
C15	0.0558 (16)	0.0381 (13)	0.0475 (15)	0.0187 (12)	0.0019 (12)	−0.0026 (11)
C16	0.0461 (14)	0.0336 (12)	0.0456 (14)	0.0146 (11)	0.0073 (11)	−0.0060 (10)
C17	0.0539 (19)	0.081 (2)	0.086 (3)	0.0190 (17)	−0.0121 (17)	0.0027 (19)
C18	0.084 (2)	0.0562 (18)	0.077 (2)	0.0113 (17)	0.0199 (19)	0.0170 (16)
C19	0.0445 (14)	0.0425 (14)	0.0461 (14)	0.0189 (11)	0.0053 (11)	0.0003 (11)
C20	0.0351 (13)	0.0477 (14)	0.0355 (13)	0.0114 (11)	0.0056 (10)	−0.0013 (11)
C21	0.0365 (13)	0.0457 (14)	0.0484 (15)	0.0122 (11)	0.0043 (11)	−0.0039 (12)
C22	0.0387 (14)	0.0526 (16)	0.0483 (15)	0.0096 (12)	0.0030 (11)	−0.0118 (12)
C23	0.0361 (13)	0.0606 (17)	0.0400 (14)	0.0088 (12)	0.0048 (11)	−0.0011 (12)
C24	0.0378 (13)	0.0491 (15)	0.0480 (15)	0.0127 (11)	0.0056 (11)	0.0090 (12)
C25	0.0342 (13)	0.0448 (14)	0.0414 (13)	0.0112 (11)	0.0100 (10)	0.0027 (11)
C26	0.0651 (19)	0.0509 (17)	0.081 (2)	0.0219 (15)	−0.0137 (16)	−0.0161 (16)
C27	0.0547 (18)	0.075 (2)	0.0468 (16)	0.0123 (15)	−0.0026 (13)	0.0025 (15)

Geometric parameters (Å, º)

Ti1—O6	1.798 (2)	C11—C16	1.400 (4)
Ti1—O5	1.839 (2)	C12—C13	1.386 (4)
Ti1—O4	1.989 (2)	C12—C17	1.520 (4)
Ti1—O2	2.002 (2)	C13—C14	1.385 (4)
Ti1—O1	2.040 (2)	C13—H13	0.9300
Ti1—O3	2.046 (2)	C14—C15	1.381 (4)
O1—C1	1.263 (4)	C14—C18	1.508 (4)
O2—C4	1.270 (3)	C15—C16	1.393 (4)
O3—C6	1.280 (3)	C15—H15	0.9300
O4—C9	1.283 (3)	C16—C19	1.512 (4)
O5—C11	1.360 (3)	C17—H17A	0.9600
O6—C20	1.352 (3)	C17—H17B	0.9600
C1—C3	1.367 (5)	C17—H17C	0.9600
C1—C2	1.518 (5)	C18—H18A	0.9600
C2—H2A	0.9600	C18—H18B	0.9600
C2—H2B	0.9600	C18—H18C	0.9600
C2—H2C	0.9600	C19—C25	1.515 (3)
C3—C4	1.376 (5)	C19—H19A	0.9700
C3—H3	0.9300	C19—H19B	0.9700
C4—C5	1.499 (5)	C20—C21	1.396 (3)
C5—H5A	0.9600	C20—C25	1.398 (3)
C5—H5B	0.9600	C21—C22	1.392 (4)
C5—H5C	0.9600	C21—C26	1.504 (4)
C6—C8	1.383 (4)	C22—C23	1.376 (4)
C6—C7	1.500 (4)	C22—H22	0.9300
C7—H7A	0.9600	C23—C24	1.390 (4)
C7—H7B	0.9600	C23—C27	1.513 (4)
C7—H7C	0.9600	C24—C25	1.388 (3)
C8—C9	1.376 (4)	C24—H24	0.9300
C8—H8	0.9300	C26—H26A	0.9600
C9—C10	1.503 (4)	C26—H26B	0.9600
C10—H10A	0.9600	C26—H26C	0.9600
C10—H10B	0.9600	C27—H27A	0.9600
C10—H10C	0.9600	C27—H27B	0.9600
C11—C12	1.399 (4)	C27—H27C	0.9600
O6—Ti1—O5	95.80 (8)	C12—C11—C16	120.8 (2)
O6—Ti1—O4	96.15 (8)	C13—C12—C11	118.5 (3)
O5—Ti1—O4	90.98 (8)	C13—C12—C17	121.9 (3)
O6—Ti1—O2	92.84 (8)	C11—C12—C17	119.6 (3)
O5—Ti1—O2	95.41 (8)	C14—C13—C12	122.5 (3)
O4—Ti1—O2	168.39 (8)	C14—C13—H13	118.7
O6—Ti1—O1	175.50 (9)	C12—C13—H13	118.7
O5—Ti1—O1	87.13 (8)	C15—C14—C13	117.4 (3)
O4—Ti1—O1	87.20 (8)	C15—C14—C18	120.9 (3)
O2—Ti1—O1	83.46 (8)	C13—C14—C18	121.7 (3)
O6—Ti1—O3	90.75 (8)	C14—C15—C16	123.0 (3)
O5—Ti1—O3	171.80 (8)	C14—C15—H15	118.5
O4—Ti1—O3	83.40 (8)	C16—C15—H15	118.5
O2—Ti1—O3	89.17 (8)	C15—C16—C11	117.7 (2)
O1—Ti1—O3	86.64 (8)	C15—C16—C19	119.9 (2)
C1—O1—Ti1	129.8 (2)	C11—C16—C19	122.4 (2)
C4—O2—Ti1	130.9 (2)	C12—C17—H17A	109.5
C6—O3—Ti1	130.3 (2)	C12—C17—H17B	109.5
C9—O4—Ti1	132.1 (2)	H17A—C17—H17B	109.5
C11—O5—Ti1	140.2 (2)	C12—C17—H17C	109.5
C20—O6—Ti1	162.5 (2)	H17A—C17—H17C	109.5
O1—C1—C3	123.7 (3)	H17B—C17—H17C	109.5
O1—C1—C2	115.3 (3)	C14—C18—H18A	109.5
C3—C1—C2	121.1 (3)	C14—C18—H18B	109.5
C1—C2—H2A	109.5	H18A—C18—H18B	109.5
C1—C2—H2B	109.5	C14—C18—H18C	109.5
H2A—C2—H2B	109.5	H18A—C18—H18C	109.5
C1—C2—H2C	109.5	H18B—C18—H18C	109.5
H2A—C2—H2C	109.5	C16—C19—C25	111.9 (2)
H2B—C2—H2C	109.5	C16—C19—H19A	109.2
C1—C3—C4	124.9 (3)	C25—C19—H19A	109.2
C1—C3—H3	117.6	C16—C19—H19B	109.2
C4—C3—H3	117.6	C25—C19—H19B	109.2
O2—C4—C3	123.2 (3)	H19A—C19—H19B	107.9
O2—C4—C5	115.7 (3)	O6—C20—C21	118.5 (2)
C3—C4—C5	121.1 (3)	O6—C20—C25	120.1 (2)
C4—C5—H5A	109.5	C21—C20—C25	121.4 (2)
C4—C5—H5B	109.5	C22—C21—C20	117.8 (2)
H5A—C5—H5B	109.5	C22—C21—C26	122.1 (2)
C4—C5—H5C	109.5	C20—C21—C26	120.1 (2)
H5A—C5—H5C	109.5	C23—C22—C21	122.8 (2)
H5B—C5—H5C	109.5	C23—C22—H22	118.6
O3—C6—C8	123.4 (3)	C21—C22—H22	118.6
O3—C6—C7	116.4 (3)	C22—C23—C24	117.7 (2)
C8—C6—C7	120.3 (3)	C22—C23—C27	121.1 (3)
C6—C7—H7A	109.5	C24—C23—C27	121.2 (3)
C6—C7—H7B	109.5	C25—C24—C23	122.4 (2)
H7A—C7—H7B	109.5	C25—C24—H24	118.8
C6—C7—H7C	109.5	C23—C24—H24	118.8
H7A—C7—H7C	109.5	C24—C25—C20	118.0 (2)
H7B—C7—H7C	109.5	C24—C25—C19	121.7 (2)
C9—C8—C6	124.0 (3)	C20—C25—C19	120.3 (2)
C9—C8—H8	118.0	C21—C26—H26A	109.5
C6—C8—H8	118.0	C21—C26—H26B	109.5
O4—C9—C8	123.6 (2)	H26A—C26—H26B	109.5
O4—C9—C10	115.0 (3)	C21—C26—H26C	109.5
C8—C9—C10	121.4 (3)	H26A—C26—H26C	109.5
C9—C10—H10A	109.5	H26B—C26—H26C	109.5
C9—C10—H10B	109.5	C23—C27—H27A	109.5
H10A—C10—H10B	109.5	C23—C27—H27B	109.5
C9—C10—H10C	109.5	H27A—C27—H27B	109.5
H10A—C10—H10C	109.5	C23—C27—H27C	109.5
H10B—C10—H10C	109.5	H27A—C27—H27C	109.5
O5—C11—C12	118.7 (2)	H27B—C27—H27C	109.5
O5—C11—C16	120.4 (2)