6-Meth-oxy-meth-oxy-7-trifluoro-methyl-1,3-benzodioxole-5-carbaldehyde.

The title compound, C(11)H(9)F(3)O(5), crystallizes with three mol-ecules in the asymmetric unit. One -CF(3) group is disordered by rotation, with the F atoms split over two sets of sites with occupancies which converged to 0.888 (6) and 0.112 (6). Weak π-π inter-actions are observed between adjacent benzene rings [the shortest centroid-centroid distance is 3.8858 (4) Å], resulting in the formation of a supra-molecular chain along [100].

Related literature

For the enhancement of the biological activity of F and CF3 containing mol­ecules compared to their unfluorinated analogues, see: Vrábel et al. (2007 ▶); Wilson & Danishefsky (2010 ▶); Bravo et al. (1994 ▶); Jung et al. (2002 ▶). For the synthesis of the title compound, an inter­mediate for the synthesis of biologic­ally active compounds, see: Corey et al. (1996 ▶); Weeratunga et al. (1987 ▶); Wu et al. (2004 ▶).

Experimental

Crystal data

C11H9F3O5

M = 278.18

Triclinic,

a = 9.3608 (10) Å

b = 12.6895 (14) Å

c = 14.6765 (16) Å

α = 97.007 (2)°

β = 93.625 (2)°

γ = 102.983 (2)°

V = 1678.7 (3) Å3

Z = 6

Mo Kα radiation

μ = 0.16 mm−1

T = 173 K

0.10 × 0.10 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.984, T max = 0.984

8355 measured reflections

5842 independent reflections

4928 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.122

S = 1.03

5842 reflections

545 parameters

18 restraints

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812022490/bh2420sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022490/bh2420Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812022490/bh2420Isup3.cml

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

C11H9F3O5	Z = 6
Mr = 278.18	F(000) = 852
Triclinic, P1	Dx = 1.651 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3608 (10) Å	Cell parameters from 4637 reflections
b = 12.6895 (14) Å	θ = 2.8–27.5°
c = 14.6765 (16) Å	µ = 0.16 mm−1
α = 97.007 (2)°	T = 173 K
β = 93.625 (2)°	Block, colourless
γ = 102.983 (2)°	0.10 × 0.10 × 0.10 mm
V = 1678.7 (3) Å3

Bruker APEXII CCD diffractometer	5842 independent reflections
Radiation source: fine-focus sealed tube	4928 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→11
Tmin = 0.984, Tmax = 0.984	k = −15→10
8355 measured reflections	l = −17→16

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0634P)2 + 0.6455P] where P = (Fo2 + 2Fc2)/3
5842 reflections	(Δ/σ)max = 0.002
545 parameters	Δρmax = 0.28 e Å−3
18 restraints	Δρmin = −0.28 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.4148 (2)	0.44220 (14)	0.24627 (12)	0.0258 (4)
C2	0.5685 (2)	0.46616 (14)	0.26506 (12)	0.0259 (4)
C3	0.6377 (2)	0.50456 (16)	0.36188 (13)	0.0322 (4)
C4	0.6498 (2)	0.45487 (14)	0.19079 (12)	0.0255 (4)
C5	0.8251 (2)	0.46037 (18)	0.09341 (13)	0.0340 (4)
H5A	0.8685	0.5324	0.0751	0.041*
H5B	0.8944	0.4126	0.0825	0.041*
C6	0.5815 (2)	0.41995 (14)	0.10140 (12)	0.0253 (4)
C7	0.4337 (2)	0.39694 (14)	0.08251 (12)	0.0254 (4)
H7	0.3894	0.3732	0.0212	0.030*
C8	0.3471 (2)	0.40933 (14)	0.15670 (12)	0.0261 (4)
C9	0.1878 (2)	0.39213 (16)	0.13658 (13)	0.0325 (4)
H9	0.1311	0.4092	0.1854	0.039*
C10	0.2684 (2)	0.36310 (17)	0.36009 (14)	0.0368 (5)
H10A	0.3165	0.3032	0.3405	0.044*
H10B	0.2849	0.3801	0.4281	0.044*
C11	0.0396 (3)	0.4048 (2)	0.3714 (2)	0.0561 (7)
H11A	−0.0659	0.3744	0.3546	0.084*
H11B	0.0701	0.4737	0.3463	0.084*
H11C	0.0591	0.4183	0.4387	0.084*
C12	0.4460 (2)	0.79048 (15)	0.33160 (12)	0.0260 (4)
C13	0.6003 (2)	0.82136 (15)	0.34819 (12)	0.0278 (4)
C14	0.6724 (2)	0.88593 (18)	0.43803 (14)	0.0377 (5)
C15	0.6789 (2)	0.78481 (15)	0.27987 (12)	0.0261 (4)
C16	0.8521 (2)	0.74583 (17)	0.19183 (14)	0.0350 (5)
H16A	0.9085	0.7991	0.1557	0.042*
H16B	0.9093	0.6907	0.2018	0.042*
C17	0.6090 (2)	0.72025 (14)	0.19871 (12)	0.0242 (4)
C18	0.4606 (2)	0.69090 (14)	0.18152 (12)	0.0257 (4)
H18	0.4149	0.6471	0.1256	0.031*
C19	0.3766 (2)	0.72763 (14)	0.24954 (12)	0.0253 (4)
C20	0.2158 (2)	0.70242 (17)	0.23068 (13)	0.0327 (4)
H20	0.1615	0.7387	0.2713	0.039*
C21	0.3062 (3)	0.7483 (2)	0.45855 (15)	0.0446 (6)
H21A	0.3602	0.6894	0.4546	0.054*
H21B	0.3214	0.7851	0.5230	0.054*
C22	0.0704 (3)	0.7777 (2)	0.4588 (2)	0.0585 (7)
H22A	−0.0336	0.7405	0.4440	0.088*
H22B	0.0947	0.8390	0.4234	0.088*
H22C	0.0887	0.8052	0.5248	0.088*
C23	0.5757 (2)	0.86851 (15)	0.85712 (13)	0.0308 (4)
C24	0.4215 (2)	0.85065 (15)	0.84339 (13)	0.0306 (4)
C25	0.3445 (3)	0.84013 (18)	0.74898 (14)	0.0396 (5)
C26	0.3451 (2)	0.84472 (14)	0.92068 (13)	0.0281 (4)
C27	0.1749 (2)	0.82327 (18)	1.02165 (13)	0.0353 (5)
H27A	0.1154	0.8752	1.0431	0.042*
H27B	0.1220	0.7488	1.0302	0.042*
C28	0.4178 (2)	0.85820 (14)	1.00856 (12)	0.0263 (4)
C29	0.5655 (2)	0.87629 (14)	1.02279 (13)	0.0282 (4)
H29	0.6132	0.8862	1.0834	0.034*
C30	0.6474 (2)	0.88013 (15)	0.94515 (13)	0.0300 (4)
C31	0.8066 (2)	0.89239 (17)	0.96167 (17)	0.0410 (5)
H31	0.8616	0.8853	0.9099	0.049*
C32	0.7103 (3)	0.97212 (17)	0.75019 (14)	0.0423 (5)
H32A	0.7049	0.9627	0.6820	0.051*
H32B	0.6487	1.0232	0.7702	0.051*
C33	0.9564 (3)	0.9601 (2)	0.7452 (2)	0.0651 (8)
H33A	1.0551	0.9917	0.7766	0.098*
H33B	0.9573	0.9680	0.6796	0.098*
H33C	0.9271	0.8825	0.7519	0.098*
F1	0.78370 (14)	0.52599 (14)	0.36687 (9)	0.0609 (4)
F2	0.59564 (16)	0.43130 (10)	0.41881 (8)	0.0491 (3)
F3	0.60334 (15)	0.59570 (9)	0.39913 (8)	0.0439 (3)
F4	0.63938 (19)	0.83087 (13)	0.50907 (9)	0.0677 (5)
F5	0.81807 (15)	0.91193 (15)	0.44024 (11)	0.0737 (5)
F6	0.63210 (16)	0.97844 (11)	0.45818 (9)	0.0548 (4)
F7	0.3831 (3)	0.93019 (15)	0.71022 (16)	0.0706 (9)	0.888 (6)
F7B	0.302 (3)	0.9299 (16)	0.7436 (13)	0.074 (6)	0.112 (6)
F8	0.3705 (3)	0.7592 (2)	0.69059 (10)	0.0583 (7)	0.888 (6)
F8B	0.431 (2)	0.827 (2)	0.6842 (10)	0.067 (5)	0.112 (6)
F9	0.1981 (2)	0.8201 (3)	0.74828 (13)	0.0635 (7)	0.888 (6)
F9B	0.231 (2)	0.7631 (17)	0.7437 (11)	0.059 (5)	0.112 (6)
O1	0.79772 (14)	0.47249 (11)	0.18950 (9)	0.0330 (3)
O2	0.68690 (14)	0.41280 (11)	0.04150 (9)	0.0324 (3)
O3	0.12449 (15)	0.35701 (13)	0.06032 (10)	0.0409 (4)
O4	0.33447 (15)	0.45868 (11)	0.31963 (9)	0.0315 (3)
O5	0.12040 (16)	0.32932 (12)	0.33439 (10)	0.0430 (4)
O6	0.82681 (14)	0.80063 (12)	0.27905 (9)	0.0368 (3)
O7	0.71247 (14)	0.69427 (11)	0.14359 (9)	0.0320 (3)
O8	0.14850 (15)	0.63790 (12)	0.16616 (10)	0.0402 (4)
O9	0.36529 (15)	0.82610 (11)	0.39864 (9)	0.0332 (3)
O10	0.15914 (18)	0.70333 (13)	0.43583 (11)	0.0484 (4)
O11	0.19842 (15)	0.82781 (12)	0.92587 (9)	0.0376 (3)
O12	0.31665 (14)	0.85179 (11)	1.07222 (9)	0.0321 (3)
O13	0.87177 (16)	0.91108 (14)	1.03801 (12)	0.0492 (4)
O14	0.65266 (17)	0.86765 (11)	0.78023 (10)	0.0403 (4)
O15	0.85359 (18)	1.01619 (12)	0.78551 (11)	0.0475 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0318 (10)	0.0228 (9)	0.0231 (9)	0.0070 (7)	0.0041 (7)	0.0030 (7)
C2	0.0323 (10)	0.0223 (9)	0.0223 (9)	0.0061 (7)	−0.0012 (7)	0.0028 (7)
C3	0.0376 (11)	0.0331 (10)	0.0251 (10)	0.0095 (9)	−0.0019 (8)	0.0012 (8)
C4	0.0261 (9)	0.0228 (9)	0.0270 (9)	0.0049 (7)	−0.0013 (7)	0.0040 (7)
C5	0.0247 (10)	0.0436 (12)	0.0313 (10)	0.0075 (9)	0.0026 (8)	−0.0035 (9)
C6	0.0287 (10)	0.0223 (9)	0.0237 (9)	0.0041 (7)	0.0028 (7)	0.0018 (7)
C7	0.0296 (10)	0.0237 (9)	0.0208 (9)	0.0040 (7)	−0.0016 (7)	0.0010 (7)
C8	0.0269 (10)	0.0233 (9)	0.0266 (9)	0.0032 (7)	0.0006 (7)	0.0037 (7)
C9	0.0303 (10)	0.0374 (11)	0.0290 (10)	0.0057 (8)	0.0030 (8)	0.0060 (8)
C10	0.0416 (12)	0.0398 (11)	0.0304 (10)	0.0076 (9)	0.0090 (9)	0.0113 (9)
C11	0.0421 (14)	0.0574 (15)	0.0715 (17)	0.0114 (12)	0.0225 (12)	0.0110 (13)
C12	0.0320 (10)	0.0260 (9)	0.0216 (9)	0.0095 (8)	0.0053 (7)	0.0037 (7)
C13	0.0333 (10)	0.0260 (9)	0.0229 (9)	0.0066 (8)	−0.0004 (8)	0.0012 (7)
C14	0.0393 (12)	0.0420 (12)	0.0280 (10)	0.0080 (9)	−0.0018 (9)	−0.0049 (9)
C15	0.0258 (9)	0.0259 (9)	0.0257 (9)	0.0040 (7)	0.0004 (7)	0.0049 (7)
C16	0.0259 (10)	0.0394 (11)	0.0363 (11)	0.0050 (8)	0.0046 (8)	−0.0034 (9)
C17	0.0291 (10)	0.0234 (9)	0.0203 (9)	0.0055 (7)	0.0047 (7)	0.0036 (7)
C18	0.0293 (10)	0.0244 (9)	0.0219 (9)	0.0039 (7)	−0.0008 (7)	0.0029 (7)
C19	0.0264 (9)	0.0266 (9)	0.0234 (9)	0.0058 (7)	0.0024 (7)	0.0061 (7)
C20	0.0291 (10)	0.0427 (11)	0.0270 (10)	0.0087 (9)	0.0045 (8)	0.0059 (9)
C21	0.0489 (14)	0.0646 (15)	0.0299 (11)	0.0241 (12)	0.0136 (10)	0.0188 (10)
C22	0.0427 (14)	0.0707 (18)	0.0671 (17)	0.0150 (13)	0.0168 (12)	0.0199 (14)
C23	0.0410 (11)	0.0205 (9)	0.0317 (10)	0.0068 (8)	0.0114 (8)	0.0032 (8)
C24	0.0410 (11)	0.0240 (9)	0.0263 (10)	0.0075 (8)	0.0019 (8)	0.0023 (7)
C25	0.0499 (14)	0.0379 (12)	0.0304 (11)	0.0103 (10)	0.0011 (10)	0.0043 (9)
C26	0.0305 (10)	0.0224 (9)	0.0310 (10)	0.0064 (7)	0.0004 (8)	0.0033 (7)
C27	0.0286 (10)	0.0443 (12)	0.0326 (10)	0.0080 (9)	0.0039 (8)	0.0044 (9)
C28	0.0310 (10)	0.0208 (9)	0.0268 (9)	0.0049 (7)	0.0036 (8)	0.0037 (7)
C29	0.0322 (10)	0.0222 (9)	0.0293 (10)	0.0044 (8)	−0.0004 (8)	0.0058 (7)
C30	0.0325 (10)	0.0214 (9)	0.0362 (11)	0.0048 (8)	0.0055 (8)	0.0060 (8)
C31	0.0351 (11)	0.0374 (12)	0.0532 (14)	0.0076 (9)	0.0125 (10)	0.0149 (10)
C32	0.0579 (14)	0.0348 (11)	0.0305 (11)	0.0005 (10)	0.0124 (10)	0.0057 (9)
C33	0.0581 (16)	0.0467 (14)	0.086 (2)	0.0018 (12)	0.0384 (15)	−0.0041 (14)
F1	0.0348 (7)	0.1043 (12)	0.0347 (7)	0.0138 (7)	−0.0097 (6)	−0.0128 (7)
F2	0.0797 (10)	0.0418 (7)	0.0255 (6)	0.0151 (7)	−0.0074 (6)	0.0086 (5)
F3	0.0665 (9)	0.0327 (6)	0.0298 (6)	0.0150 (6)	−0.0069 (6)	−0.0059 (5)
F4	0.1021 (12)	0.0654 (10)	0.0266 (7)	0.0079 (9)	−0.0151 (7)	0.0041 (6)
F5	0.0385 (8)	0.1045 (13)	0.0585 (9)	0.0084 (8)	−0.0117 (7)	−0.0416 (9)
F6	0.0660 (9)	0.0422 (7)	0.0490 (8)	0.0134 (7)	−0.0026 (7)	−0.0187 (6)
F7	0.100 (2)	0.0513 (11)	0.0553 (13)	0.0039 (11)	−0.0237 (12)	0.0275 (9)
F7B	0.090 (10)	0.087 (9)	0.060 (8)	0.041 (8)	0.001 (7)	0.027 (7)
F8	0.0898 (16)	0.0586 (14)	0.0277 (8)	0.0307 (12)	−0.0052 (8)	−0.0091 (8)
F8B	0.071 (8)	0.080 (10)	0.044 (7)	0.015 (7)	−0.002 (6)	−0.001 (6)
F9	0.0491 (11)	0.102 (2)	0.0359 (9)	0.0194 (12)	−0.0100 (7)	−0.0001 (11)
F9B	0.042 (7)	0.065 (9)	0.056 (7)	−0.011 (6)	−0.016 (6)	0.012 (7)
O1	0.0248 (7)	0.0443 (8)	0.0283 (7)	0.0074 (6)	−0.0019 (5)	0.0019 (6)
O2	0.0266 (7)	0.0425 (8)	0.0255 (7)	0.0059 (6)	0.0037 (5)	−0.0018 (6)
O3	0.0273 (7)	0.0540 (9)	0.0351 (8)	0.0020 (7)	−0.0033 (6)	−0.0017 (7)
O4	0.0358 (7)	0.0327 (7)	0.0260 (7)	0.0067 (6)	0.0094 (6)	0.0026 (5)
O5	0.0402 (9)	0.0381 (8)	0.0459 (9)	0.0005 (7)	0.0076 (7)	0.0018 (7)
O6	0.0254 (7)	0.0481 (9)	0.0310 (7)	0.0023 (6)	0.0004 (6)	−0.0042 (6)
O7	0.0250 (7)	0.0414 (8)	0.0275 (7)	0.0067 (6)	0.0041 (5)	−0.0026 (6)
O8	0.0291 (7)	0.0477 (9)	0.0380 (8)	0.0017 (6)	−0.0017 (6)	−0.0002 (7)
O9	0.0367 (8)	0.0392 (8)	0.0259 (7)	0.0136 (6)	0.0089 (6)	0.0018 (6)
O10	0.0526 (10)	0.0443 (9)	0.0478 (9)	0.0061 (7)	0.0148 (8)	0.0091 (7)
O11	0.0298 (7)	0.0524 (9)	0.0307 (7)	0.0103 (6)	−0.0004 (6)	0.0070 (6)
O12	0.0287 (7)	0.0409 (8)	0.0264 (7)	0.0072 (6)	0.0041 (5)	0.0044 (6)
O13	0.0317 (8)	0.0565 (10)	0.0582 (11)	0.0059 (7)	−0.0002 (7)	0.0138 (8)
O14	0.0552 (9)	0.0282 (7)	0.0364 (8)	0.0045 (6)	0.0207 (7)	0.0017 (6)
O15	0.0506 (10)	0.0347 (8)	0.0508 (9)	−0.0011 (7)	0.0165 (8)	−0.0044 (7)

C1—O4	1.373 (2)	C18—C19	1.408 (3)
C1—C8	1.395 (3)	C18—H18	0.9500
C1—C2	1.404 (3)	C19—C20	1.467 (3)
C2—C4	1.380 (3)	C20—O8	1.212 (2)
C2—C3	1.500 (2)	C20—H20	0.9500
C3—F1	1.327 (2)	C21—O10	1.369 (3)
C3—F3	1.332 (2)	C21—O9	1.443 (2)
C3—F2	1.336 (2)	C21—H21A	0.9900
C4—O1	1.354 (2)	C21—H21B	0.9900
C4—C6	1.397 (3)	C22—O10	1.416 (3)
C5—O2	1.425 (2)	C22—H22A	0.9800
C5—O1	1.445 (2)	C22—H22B	0.9800
C5—H5A	0.9900	C22—H22C	0.9800
C5—H5B	0.9900	C23—O14	1.377 (2)
C6—C7	1.352 (3)	C23—C30	1.393 (3)
C6—O2	1.373 (2)	C23—C24	1.407 (3)
C7—C8	1.412 (3)	C24—C26	1.379 (3)
C7—H7	0.9500	C24—C25	1.497 (3)
C8—C9	1.464 (3)	C25—F9B	1.266 (15)
C9—O3	1.216 (2)	C25—F8B	1.304 (16)
C9—H9	0.9500	C25—F7B	1.300 (18)
C10—O5	1.368 (2)	C25—F7	1.326 (3)
C10—O4	1.446 (2)	C25—F9	1.336 (3)
C10—H10A	0.9900	C25—F8	1.331 (3)
C10—H10B	0.9900	C26—O11	1.350 (2)
C11—O5	1.427 (3)	C26—C28	1.392 (3)
C11—H11A	0.9800	C27—O12	1.427 (2)
C11—H11B	0.9800	C27—O11	1.443 (2)
C11—H11C	0.9800	C27—H27A	0.9900
C12—O9	1.372 (2)	C27—H27B	0.9900
C12—C19	1.394 (3)	C28—C29	1.348 (3)
C12—C13	1.406 (3)	C28—O12	1.368 (2)
C13—C15	1.377 (3)	C29—C30	1.413 (3)
C13—C14	1.497 (3)	C29—H29	0.9500
C14—F6	1.318 (3)	C30—C31	1.465 (3)
C14—F5	1.326 (3)	C31—O13	1.211 (3)
C14—F4	1.339 (3)	C31—H31	0.9500
C15—O6	1.355 (2)	C32—O15	1.373 (3)
C15—C17	1.393 (3)	C32—O14	1.447 (2)
C16—O7	1.422 (2)	C32—H32A	0.9900
C16—O6	1.440 (2)	C32—H32B	0.9900
C16—H16A	0.9900	C33—O15	1.435 (3)
C16—H16B	0.9900	C33—H33A	0.9800
C17—C18	1.353 (3)	C33—H33B	0.9800
C17—O7	1.371 (2)	C33—H33C	0.9800
O4—C1—C8	121.40 (16)	O8—C20—C19	123.64 (18)
O4—C1—C2	116.80 (15)	O8—C20—H20	118.2
C8—C1—C2	121.70 (16)	C19—C20—H20	118.2
C4—C2—C1	116.89 (16)	O10—C21—O9	112.04 (17)
C4—C2—C3	122.85 (17)	O10—C21—H21A	109.2
C1—C2—C3	120.25 (16)	O9—C21—H21A	109.2
F1—C3—F3	106.24 (16)	O10—C21—H21B	109.2
F1—C3—F2	106.72 (16)	O9—C21—H21B	109.2
F3—C3—F2	105.70 (16)	H21A—C21—H21B	107.9
F1—C3—C2	112.31 (16)	O10—C22—H22A	109.5
F3—C3—C2	112.74 (16)	O10—C22—H22B	109.5
F2—C3—C2	112.61 (16)	H22A—C22—H22B	109.5
O1—C4—C2	128.95 (16)	O10—C22—H22C	109.5
O1—C4—C6	109.80 (16)	H22A—C22—H22C	109.5
C2—C4—C6	121.24 (17)	H22B—C22—H22C	109.5
O2—C5—O1	107.09 (14)	O14—C23—C30	120.96 (18)
O2—C5—H5A	110.3	O14—C23—C24	117.75 (17)
O1—C5—H5A	110.3	C30—C23—C24	121.18 (17)
O2—C5—H5B	110.3	C26—C24—C23	117.07 (17)
O1—C5—H5B	110.3	C26—C24—C25	121.70 (18)
H5A—C5—H5B	108.6	C23—C24—C25	121.22 (18)
C7—C6—O2	128.38 (16)	F9B—C25—F8B	113.5 (12)
C7—C6—C4	122.35 (17)	F9B—C25—F7B	107.7 (12)
O2—C6—C4	109.26 (16)	F8B—C25—F7B	109.0 (12)
C6—C7—C8	117.95 (16)	F7—C25—F9	105.5 (2)
C6—C7—H7	121.0	F7—C25—F8	106.5 (2)
C8—C7—H7	121.0	F9—C25—F8	105.2 (2)
C1—C8—C7	119.84 (17)	F7—C25—C24	112.52 (18)
C1—C8—C9	121.52 (17)	F9—C25—C24	113.25 (18)
C7—C8—C9	118.57 (16)	F8—C25—C24	113.20 (18)
O3—C9—C8	123.04 (18)	O11—C26—C24	128.49 (17)
O3—C9—H9	118.5	O11—C26—C28	110.13 (16)
C8—C9—H9	118.5	C24—C26—C28	121.38 (18)
O5—C10—O4	111.60 (16)	O12—C27—O11	106.96 (15)
O5—C10—H10A	109.3	O12—C27—H27A	110.3
O4—C10—H10A	109.3	O11—C27—H27A	110.3
O5—C10—H10B	109.3	O12—C27—H27B	110.3
O4—C10—H10B	109.3	O11—C27—H27B	110.3
H10A—C10—H10B	108.0	H27A—C27—H27B	108.6
O5—C11—H11A	109.5	C29—C28—O12	128.65 (17)
O5—C11—H11B	109.5	C29—C28—C26	122.17 (17)
H11A—C11—H11B	109.5	O12—C28—C26	109.17 (16)
O5—C11—H11C	109.5	C28—C29—C30	118.16 (17)
H11A—C11—H11C	109.5	C28—C29—H29	120.9
H11B—C11—H11C	109.5	C30—C29—H29	120.9
O9—C12—C19	120.80 (16)	C23—C30—C29	120.00 (18)
O9—C12—C13	117.59 (16)	C23—C30—C31	122.72 (18)
C19—C12—C13	121.61 (16)	C29—C30—C31	117.23 (18)
C15—C13—C12	116.53 (16)	O13—C31—C30	123.3 (2)
C15—C13—C14	122.72 (17)	O13—C31—H31	118.4
C12—C13—C14	120.69 (17)	C30—C31—H31	118.4
F6—C14—F5	106.30 (18)	O15—C32—O14	111.72 (18)
F6—C14—F4	105.33 (17)	O15—C32—H32A	109.3
F5—C14—F4	106.69 (18)	O14—C32—H32A	109.3
F6—C14—C13	113.57 (17)	O15—C32—H32B	109.3
F5—C14—C13	112.56 (17)	O14—C32—H32B	109.3
F4—C14—C13	111.84 (17)	H32A—C32—H32B	107.9
O6—C15—C13	128.50 (16)	O15—C33—H33A	109.5
O6—C15—C17	109.80 (16)	O15—C33—H33B	109.5
C13—C15—C17	121.68 (17)	H33A—C33—H33B	109.5
O7—C16—O6	107.78 (15)	O15—C33—H33C	109.5
O7—C16—H16A	110.2	H33A—C33—H33C	109.5
O6—C16—H16A	110.2	H33B—C33—H33C	109.5
O7—C16—H16B	110.2	C4—O1—C5	106.13 (13)
O6—C16—H16B	110.2	C6—O2—C5	106.07 (14)
H16A—C16—H16B	108.5	C1—O4—C10	116.60 (14)
C18—C17—O7	128.01 (16)	C10—O5—C11	112.88 (17)
C18—C17—C15	122.36 (17)	C15—O6—C16	106.43 (14)
O7—C17—C15	109.63 (15)	C17—O7—C16	106.33 (14)
C17—C18—C19	117.56 (16)	C12—O9—C21	116.13 (15)
C17—C18—H18	121.2	C21—O10—C22	112.81 (19)
C19—C18—H18	121.2	C26—O11—C27	106.53 (14)
C12—C19—C18	120.25 (16)	C28—O12—C27	106.64 (14)
C12—C19—C20	120.90 (17)	C23—O14—C32	116.82 (15)
C18—C19—C20	118.80 (16)	C32—O15—C33	113.45 (18)
O4—C1—C2—C4	−176.86 (15)	C26—C24—C25—F9B	−42.5 (13)
C8—C1—C2—C4	−0.5 (3)	C23—C24—C25—F9B	138.4 (12)
O4—C1—C2—C3	1.8 (2)	C26—C24—C25—F8B	−167.6 (12)
C8—C1—C2—C3	178.13 (16)	C23—C24—C25—F8B	13.2 (12)
C4—C2—C3—F1	0.1 (3)	C26—C24—C25—F7B	72.8 (13)
C1—C2—C3—F1	−178.42 (17)	C23—C24—C25—F7B	−106.4 (13)
C4—C2—C3—F3	120.10 (19)	C26—C24—C25—F7	116.7 (3)
C1—C2—C3—F3	−58.4 (2)	C23—C24—C25—F7	−62.4 (3)
C4—C2—C3—F2	−120.39 (19)	C26—C24—C25—F9	−2.8 (3)
C1—C2—C3—F2	61.1 (2)	C23—C24—C25—F9	178.0 (2)
C1—C2—C4—O1	179.94 (17)	C26—C24—C25—F8	−122.5 (2)
C3—C2—C4—O1	1.4 (3)	C23—C24—C25—F8	58.3 (3)
C1—C2—C4—C6	−0.7 (3)	C23—C24—C26—O11	−179.62 (17)
C3—C2—C4—C6	−179.32 (17)	C25—C24—C26—O11	1.2 (3)
O1—C4—C6—C7	−179.61 (16)	C23—C24—C26—C28	1.4 (3)
C2—C4—C6—C7	0.9 (3)	C25—C24—C26—C28	−177.84 (17)
O1—C4—C6—O2	1.2 (2)	O11—C26—C28—C29	179.98 (16)
C2—C4—C6—O2	−178.25 (16)	C24—C26—C28—C29	−0.8 (3)
O2—C6—C7—C8	179.14 (17)	O11—C26—C28—O12	−1.0 (2)
C4—C6—C7—C8	0.1 (3)	C24—C26—C28—O12	178.14 (16)
O4—C1—C8—C7	177.74 (16)	O12—C28—C29—C30	−179.55 (17)
C2—C1—C8—C7	1.5 (3)	C26—C28—C29—C30	−0.8 (3)
O4—C1—C8—C9	0.7 (3)	O14—C23—C30—C29	−177.40 (16)
C2—C1—C8—C9	−175.48 (17)	C24—C23—C30—C29	−1.3 (3)
C6—C7—C8—C1	−1.3 (3)	O14—C23—C30—C31	0.2 (3)
C6—C7—C8—C9	175.79 (16)	C24—C23—C30—C31	176.32 (17)
C1—C8—C9—O3	−175.27 (18)	C28—C29—C30—C23	1.8 (3)
C7—C8—C9—O3	7.7 (3)	C28—C29—C30—C31	−175.92 (17)
O9—C12—C13—C15	−179.89 (15)	C23—C30—C31—O13	174.0 (2)
C19—C12—C13—C15	−1.0 (3)	C29—C30—C31—O13	−8.3 (3)
O9—C12—C13—C14	3.1 (3)	C2—C4—O1—C5	−173.78 (18)
C19—C12—C13—C14	−178.07 (17)	C6—C4—O1—C5	6.8 (2)
C15—C13—C14—F6	126.8 (2)	O2—C5—O1—C4	−12.1 (2)
C12—C13—C14—F6	−56.4 (3)	C7—C6—O2—C5	172.08 (18)
C15—C13—C14—F5	5.9 (3)	C4—C6—O2—C5	−8.79 (19)
C12—C13—C14—F5	−177.21 (18)	O1—C5—O2—C6	12.8 (2)
C15—C13—C14—F4	−114.2 (2)	C8—C1—O4—C10	83.8 (2)
C12—C13—C14—F4	62.7 (2)	C2—C1—O4—C10	−99.78 (19)
C12—C13—C15—O6	−178.52 (17)	O5—C10—O4—C1	−103.73 (19)
C14—C13—C15—O6	−1.5 (3)	O4—C10—O5—C11	−67.4 (2)
C12—C13—C15—C17	−0.2 (3)	C13—C15—O6—C16	−179.92 (19)
C14—C13—C15—C17	176.76 (18)	C17—C15—O6—C16	1.6 (2)
O6—C15—C17—C18	179.50 (16)	O7—C16—O6—C15	−2.1 (2)
C13—C15—C17—C18	0.9 (3)	C18—C17—O7—C16	179.16 (18)
O6—C15—C17—O7	−0.6 (2)	C15—C17—O7—C16	−0.75 (19)
C13—C15—C17—O7	−179.15 (16)	O6—C16—O7—C17	1.7 (2)
O7—C17—C18—C19	179.76 (16)	C19—C12—O9—C21	81.4 (2)
C15—C17—C18—C19	−0.3 (3)	C13—C12—O9—C21	−99.8 (2)
O9—C12—C19—C18	−179.54 (15)	O10—C21—O9—C12	−102.7 (2)
C13—C12—C19—C18	1.6 (3)	O9—C21—O10—C22	−71.9 (2)
O9—C12—C19—C20	3.1 (3)	C24—C26—O11—C27	177.13 (19)
C13—C12—C19—C20	−175.78 (17)	C28—C26—O11—C27	−3.8 (2)
C17—C18—C19—C12	−0.9 (3)	O12—C27—O11—C26	7.0 (2)
C17—C18—C19—C20	176.55 (16)	C29—C28—O12—C27	−175.68 (19)
C12—C19—C20—O8	−170.82 (18)	C26—C28—O12—C27	5.4 (2)
C18—C19—C20—O8	11.7 (3)	O11—C27—O12—C28	−7.6 (2)
O14—C23—C24—C26	175.93 (16)	C30—C23—O14—C32	−89.6 (2)
C30—C23—C24—C26	−0.3 (3)	C24—C23—O14—C32	94.2 (2)
O14—C23—C24—C25	−4.9 (3)	O15—C32—O14—C23	94.5 (2)
C30—C23—C24—C25	178.90 (17)	O14—C32—O15—C33	71.4 (2)