1,3,5-Tris(4-formyl­phenoxy­methyl)-2,4,6-tri­methyl­benzene ethyl acetate solvate

In the crystal structure of the title compound, C₃₃H₃₀O₆·C₄H₈O₂, two 4-formyl­phenoxy pendant arms protrude on one side of the mean plane of the central benzene ring and the other protrudes on the opposite side. The mol­ecules are arranged in chains parallel to the a axis that propagate via edge-to-face aryl-aryl intractions. Each chain is connected to four adjacent chains, also by edge-to-face interactions, to produce a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.053
• wR factor = 0.147
• Data-to-parameter ratio = 18.6

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT413_ALERT_2_C Short Inter XH3 .. XHn     H31    ..  H34A     =       2.10 Ang.

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

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

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Computing details

Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT and XPREP (Siemens, 1995); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and WinGX32 (Farrugia, 1999); software used to prepare material for publication: enCIFer (CCDC, 2003).

2,4,6-Trimethyl-1,3,5-tris(4-formylphenoxymethyl)benzene ethyl acetate solvate

Crystal data

C33H30O6·C4H8O2	F(000) = 1296
Mr = 610.67	Dx = 1.277 Mg m^−3
Monoclinic, P21/n	Melting point: 475 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 9.242 (2) Å	Cell parameters from 8567 reflections
b = 27.044 (7) Å	θ = 2.3–28.2°
c = 12.722 (3) Å	µ = 0.09 mm^−1
β = 92.862 (4)°	T = 150 K
V = 3176.0 (14) Å^3	Multi-faceted, colourless
Z = 4	0.35 × 0.26 × 0.15 mm

Data collection

Bruker SMART1000 CCD diffractometer	7627 independent reflections
Radiation source: sealed tube	5510 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
ω scans	θmax = 28.3°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	h = −12→12
Tmin = 0.876, Tmax = 0.990	k = −35→34
31250 measured reflections	l = −16→16

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.147	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0723P)^2 + 1.0037P] where P = (Fo^2 + 2Fc^2)/3
7627 reflections	(Δ/σ)max < 0.001
409 parameters	Δρmax = 0.32 e Å^−3
6 restraints	Δρmin = −0.20 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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.53486 (17)	0.40503 (6)	0.60168 (13)	0.0314 (4)
C2	0.57762 (17)	0.38046 (6)	0.51137 (13)	0.0313 (4)
C3	0.67207 (17)	0.40375 (6)	0.44448 (13)	0.0294 (3)
C4	0.72042 (17)	0.45233 (6)	0.46482 (12)	0.0294 (3)
C5	0.67280 (17)	0.47703 (6)	0.55351 (12)	0.0286 (3)
C6	0.58070 (17)	0.45367 (6)	0.62249 (12)	0.0306 (3)
C7	0.43548 (18)	0.37911 (7)	0.67439 (14)	0.0359 (4)
H7A	0.4570	0.3433	0.6771	0.043*
H7B	0.4478	0.3928	0.7465	0.043*
C8	0.17832 (18)	0.36503 (6)	0.68005 (14)	0.0337 (4)
C9	0.19702 (19)	0.33303 (6)	0.76550 (14)	0.0347 (4)
H9	0.2913	0.3253	0.7940	0.042*
C10	0.07550 (19)	0.31271 (7)	0.80813 (14)	0.0378 (4)
H10	0.0873	0.2907	0.8662	0.045*
C11	−0.06375 (19)	0.32378 (7)	0.76779 (15)	0.0399 (4)
C12	−0.0806 (2)	0.35570 (7)	0.68120 (15)	0.0437 (4)
H12	−0.1748	0.3633	0.6524	0.052*
C13	0.0389 (2)	0.37600 (7)	0.63801 (15)	0.0416 (4)
H13	0.0270	0.3976	0.5793	0.050*
C14	−0.1888 (2)	0.30124 (8)	0.81520 (17)	0.0496 (5)
H14	−0.1704	0.2806	0.8748	0.059*
C15	0.5220 (2)	0.32896 (6)	0.48516 (16)	0.0424 (4)
H15A	0.5960	0.3045	0.5069	0.064*
H15B	0.5006	0.3263	0.4091	0.064*
H15C	0.4336	0.3227	0.5225	0.064*
C16	0.71523 (19)	0.37607 (6)	0.34805 (13)	0.0347 (4)
H16A	0.8091	0.3884	0.3245	0.042*
H16B	0.7246	0.3403	0.3633	0.042*
C17	0.57229 (18)	0.34932 (6)	0.19311 (13)	0.0319 (4)
C18	0.4474 (2)	0.35705 (7)	0.12843 (14)	0.0382 (4)
H18	0.3908	0.3859	0.1370	0.046*
C19	0.40656 (19)	0.32293 (7)	0.05253 (14)	0.0366 (4)
H19	0.3218	0.3283	0.0086	0.044*
C20	0.48925 (19)	0.28037 (6)	0.03983 (13)	0.0338 (4)
C21	0.6148 (2)	0.27388 (7)	0.10332 (14)	0.0398 (4)
H21	0.6726	0.2454	0.0937	0.048*
C22	0.65776 (19)	0.30778 (6)	0.18008 (14)	0.0362 (4)
H22	0.7437	0.3028	0.2228	0.043*
C23	0.4467 (2)	0.24225 (7)	−0.03752 (15)	0.0446 (5)
H23	0.5078	0.2141	−0.0404	0.054*
C24	0.8198 (2)	0.47763 (7)	0.39038 (15)	0.0423 (4)
H24A	0.9181	0.4791	0.4228	0.064*
H24B	0.7847	0.5113	0.3757	0.064*
H24C	0.8207	0.4589	0.3245	0.064*
C25	0.71473 (18)	0.52995 (6)	0.57510 (13)	0.0317 (4)
H25A	0.7637	0.5439	0.5143	0.038*
H25B	0.6273	0.5500	0.5865	0.038*
C26	0.84450 (17)	0.57652 (6)	0.70922 (13)	0.0313 (3)
C27	0.8096 (2)	0.62106 (6)	0.65970 (14)	0.0363 (4)
H27	0.7596	0.6216	0.5926	0.044*
C28	0.8493 (2)	0.66476 (6)	0.71047 (15)	0.0403 (4)
H28	0.8245	0.6954	0.6777	0.048*
C29	0.92417 (19)	0.66500 (6)	0.80748 (14)	0.0370 (4)
C30	0.9591 (2)	0.62006 (7)	0.85553 (15)	0.0404 (4)
H30	1.0106	0.6197	0.9221	0.049*
C31	0.9198 (2)	0.57630 (7)	0.80750 (15)	0.0395 (4)
H31	0.9437	0.5458	0.8410	0.047*
C32	0.9645 (2)	0.71189 (7)	0.85977 (17)	0.0480 (5)
H32	0.9380	0.7417	0.8245	0.058*
C33	0.5317 (2)	0.48163 (7)	0.71738 (14)	0.0405 (4)
H33A	0.6110	0.4829	0.7714	0.061*
H33B	0.4482	0.4648	0.7457	0.061*
H33C	0.5040	0.5153	0.6965	0.061*
C34	0.0734 (2)	0.44918 (8)	0.8848 (2)	0.0561 (6)
H34A	−0.0019	0.4742	0.8928	0.084*	0.50
H34B	0.0515	0.4200	0.9267	0.084*	0.50
H34C	0.0765	0.4398	0.8105	0.084*	0.50
H34D	0.0859	0.4151	0.8605	0.084*	0.50
H34E	0.0325	0.4694	0.8266	0.084*	0.50
H34F	0.0076	0.4495	0.9428	0.084*	0.50
C35	0.2158 (2)	0.46964 (8)	0.92161 (16)	0.0466 (5)
C36	0.3385 (2)	0.54130 (9)	0.98904 (17)	0.0521 (5)
H36A	0.3966	0.5485	0.9276	0.063*
H36B	0.3962	0.5194	1.0375	0.063*
C37	0.3035 (2)	0.58852 (9)	1.04422 (19)	0.0563 (5)
H37A	0.3936	0.6051	1.0677	0.084*
H37B	0.2466	0.5811	1.1052	0.084*
H37C	0.2474	0.6102	0.9957	0.084*
O1	0.28870 (12)	0.38756 (5)	0.63175 (10)	0.0377 (3)
O2	−0.31452 (15)	0.30681 (6)	0.78448 (13)	0.0599 (4)
O3	0.60068 (14)	0.38482 (4)	0.26747 (10)	0.0411 (3)
O4	0.34181 (16)	0.24312 (5)	−0.09789 (12)	0.0533 (4)
O5	0.81140 (13)	0.53118 (4)	0.66817 (9)	0.0351 (3)
O6	1.02915 (17)	0.71504 (5)	0.94454 (13)	0.0578 (4)
O7	0.32936 (17)	0.44799 (6)	0.92173 (15)	0.0687 (5)
O8	0.20456 (15)	0.51678 (5)	0.95454 (12)	0.0504 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0286 (8)	0.0310 (8)	0.0340 (8)	0.0007 (6)	−0.0054 (6)	0.0076 (7)
C2	0.0309 (8)	0.0254 (8)	0.0365 (9)	0.0015 (6)	−0.0090 (7)	0.0035 (7)
C3	0.0296 (8)	0.0275 (8)	0.0302 (8)	0.0040 (6)	−0.0068 (6)	0.0001 (6)
C4	0.0283 (8)	0.0296 (8)	0.0298 (8)	0.0013 (6)	−0.0042 (6)	0.0011 (6)
C5	0.0304 (8)	0.0253 (8)	0.0292 (8)	0.0023 (6)	−0.0063 (6)	−0.0001 (6)
C6	0.0313 (8)	0.0313 (8)	0.0285 (8)	0.0046 (6)	−0.0052 (6)	0.0018 (6)
C7	0.0312 (8)	0.0370 (9)	0.0388 (9)	0.0003 (7)	−0.0051 (7)	0.0118 (7)
C8	0.0339 (8)	0.0311 (8)	0.0356 (9)	−0.0014 (7)	−0.0025 (7)	0.0025 (7)
C9	0.0343 (9)	0.0319 (9)	0.0371 (9)	−0.0007 (7)	−0.0066 (7)	0.0047 (7)
C10	0.0397 (9)	0.0344 (9)	0.0388 (9)	−0.0045 (7)	−0.0033 (7)	0.0069 (7)
C11	0.0356 (9)	0.0418 (10)	0.0418 (10)	−0.0064 (7)	−0.0044 (8)	0.0027 (8)
C12	0.0338 (9)	0.0480 (11)	0.0482 (11)	−0.0024 (8)	−0.0101 (8)	0.0060 (9)
C13	0.0392 (10)	0.0439 (10)	0.0408 (10)	−0.0008 (8)	−0.0083 (8)	0.0122 (8)
C14	0.0429 (11)	0.0550 (12)	0.0499 (11)	−0.0123 (9)	−0.0068 (9)	0.0052 (9)
C15	0.0466 (10)	0.0266 (9)	0.0532 (11)	−0.0036 (7)	−0.0050 (9)	0.0022 (8)
C16	0.0397 (9)	0.0304 (8)	0.0331 (9)	0.0054 (7)	−0.0074 (7)	−0.0044 (7)
C17	0.0396 (9)	0.0281 (8)	0.0277 (8)	0.0019 (7)	−0.0011 (7)	−0.0011 (6)
C18	0.0418 (10)	0.0371 (9)	0.0351 (9)	0.0122 (8)	−0.0046 (7)	−0.0030 (7)
C19	0.0329 (9)	0.0416 (10)	0.0344 (9)	0.0048 (7)	−0.0071 (7)	−0.0010 (7)
C20	0.0398 (9)	0.0308 (8)	0.0305 (8)	−0.0007 (7)	−0.0014 (7)	−0.0014 (7)
C21	0.0464 (10)	0.0334 (9)	0.0387 (9)	0.0112 (8)	−0.0079 (8)	−0.0062 (7)
C22	0.0368 (9)	0.0358 (9)	0.0350 (9)	0.0086 (7)	−0.0068 (7)	−0.0046 (7)
C23	0.0562 (12)	0.0349 (10)	0.0415 (10)	0.0028 (8)	−0.0102 (9)	−0.0052 (8)
C24	0.0471 (10)	0.0361 (10)	0.0447 (10)	−0.0061 (8)	0.0107 (8)	−0.0058 (8)
C25	0.0387 (9)	0.0264 (8)	0.0291 (8)	0.0011 (7)	−0.0075 (7)	−0.0003 (6)
C26	0.0318 (8)	0.0270 (8)	0.0346 (9)	0.0015 (6)	−0.0020 (7)	−0.0041 (6)
C27	0.0457 (10)	0.0317 (9)	0.0307 (8)	0.0013 (7)	−0.0054 (7)	−0.0004 (7)
C28	0.0518 (11)	0.0264 (9)	0.0425 (10)	0.0009 (7)	−0.0009 (8)	0.0010 (7)
C29	0.0370 (9)	0.0332 (9)	0.0406 (10)	−0.0014 (7)	0.0009 (7)	−0.0085 (7)
C30	0.0400 (10)	0.0414 (10)	0.0386 (10)	0.0029 (8)	−0.0108 (8)	−0.0084 (8)
C31	0.0442 (10)	0.0321 (9)	0.0409 (10)	0.0058 (7)	−0.0118 (8)	−0.0005 (7)
C32	0.0523 (12)	0.0356 (10)	0.0556 (12)	−0.0003 (8)	−0.0013 (10)	−0.0112 (9)
C33	0.0454 (10)	0.0428 (10)	0.0334 (9)	0.0039 (8)	0.0035 (8)	−0.0009 (8)
C34	0.0585 (13)	0.0378 (11)	0.0732 (15)	0.0044 (9)	0.0153 (11)	−0.0049 (10)
C35	0.0522 (12)	0.0440 (11)	0.0449 (11)	0.0116 (9)	0.0144 (9)	0.0068 (9)
C36	0.0417 (10)	0.0653 (14)	0.0490 (12)	0.0043 (10)	−0.0010 (9)	−0.0009 (10)
C37	0.0482 (12)	0.0582 (13)	0.0614 (14)	0.0015 (10)	−0.0068 (10)	−0.0012 (11)
O1	0.0318 (6)	0.0402 (7)	0.0404 (7)	−0.0009 (5)	−0.0041 (5)	0.0144 (5)
O2	0.0371 (8)	0.0751 (11)	0.0665 (10)	−0.0131 (7)	−0.0063 (7)	0.0052 (8)
O3	0.0545 (8)	0.0309 (6)	0.0362 (7)	0.0122 (5)	−0.0161 (6)	−0.0075 (5)
O4	0.0606 (9)	0.0443 (8)	0.0524 (8)	−0.0034 (7)	−0.0225 (7)	−0.0071 (6)
O5	0.0414 (6)	0.0250 (6)	0.0376 (7)	0.0030 (5)	−0.0123 (5)	−0.0028 (5)
O6	0.0608 (9)	0.0504 (9)	0.0607 (9)	0.0009 (7)	−0.0098 (7)	−0.0238 (7)
O7	0.0565 (9)	0.0642 (10)	0.0866 (12)	0.0183 (8)	0.0150 (9)	−0.0035 (9)
O8	0.0445 (8)	0.0445 (8)	0.0617 (9)	0.0081 (6)	−0.0005 (6)	−0.0006 (7)

Geometric parameters (Å, º)

C1—C2	1.401 (2)	C21—C22	1.383 (2)
C1—C6	1.403 (2)	C21—H21	0.9500
C1—C7	1.509 (2)	C22—H22	0.9500
C2—C3	1.399 (2)	C23—O4	1.207 (2)
C2—C15	1.516 (2)	C23—H23	0.9500
C3—C4	1.407 (2)	C24—H24A	0.9800
C3—C16	1.508 (2)	C24—H24B	0.9800
C4—C5	1.401 (2)	C24—H24C	0.9800
C4—C24	1.515 (2)	C25—O5	1.4476 (19)
C5—C6	1.403 (2)	C25—H25A	0.9900
C5—C25	1.505 (2)	C25—H25B	0.9900
C6—C33	1.513 (2)	C26—O5	1.3618 (19)
C7—O1	1.4537 (19)	C26—C27	1.390 (2)
C7—H7A	0.9900	C26—C31	1.400 (2)
C7—H7B	0.9900	C27—C28	1.388 (2)
C8—O1	1.361 (2)	C27—H27	0.9500
C8—C9	1.394 (2)	C28—C29	1.384 (3)
C8—C13	1.402 (2)	C28—H28	0.9500
C9—C10	1.385 (2)	C29—C30	1.391 (3)
C9—H9	0.9500	C29—C32	1.471 (2)
C10—C11	1.394 (2)	C30—C31	1.373 (3)
C10—H10	0.9500	C30—H30	0.9500
C11—C12	1.402 (3)	C31—H31	0.9500
C11—C14	1.464 (3)	C32—O6	1.209 (2)
C12—C13	1.373 (3)	C32—H32	0.9500
C12—H12	0.9500	C33—H33A	0.9800
C13—H13	0.9500	C33—H33B	0.9800
C14—O2	1.216 (2)	C33—H33C	0.9800
C14—H14	0.9500	C34—C35	1.482 (3)
C15—H15A	0.9800	C34—H34A	0.9800
C15—H15B	0.9800	C34—H34B	0.9800
C15—H15C	0.9800	C34—H34C	0.9800
C16—O3	1.456 (2)	C34—H34D	0.9800
C16—H16A	0.9900	C34—H34E	0.9800
C16—H16B	0.9900	C34—H34F	0.9800
C17—O3	1.364 (2)	C35—O7	1.202 (2)
C17—C22	1.388 (2)	C35—O8	1.347 (2)
C17—C18	1.399 (2)	C36—O8	1.453 (3)
C18—C19	1.375 (2)	C36—C37	1.500 (3)
C18—H18	0.9500	C36—H36A	0.9900
C19—C20	1.395 (2)	C36—H36B	0.9900
C19—H19	0.9500	C37—H37A	0.9800
C20—C21	1.391 (2)	C37—H37B	0.9800
C20—C23	1.465 (2)	C37—H37C	0.9800
C2—C1—C6	120.30 (15)	C4—C24—H24B	109.5
C2—C1—C7	119.19 (15)	H24A—C24—H24B	109.5
C6—C1—C7	120.49 (16)	C4—C24—H24C	109.5
C3—C2—C1	119.69 (15)	H24A—C24—H24C	109.5
C3—C2—C15	119.66 (16)	H24B—C24—H24C	109.5
C1—C2—C15	120.65 (16)	O5—C25—C5	108.30 (12)
C2—C3—C4	120.70 (15)	O5—C25—H25A	110.0
C2—C3—C16	118.03 (15)	C5—C25—H25A	110.0
C4—C3—C16	121.23 (15)	O5—C25—H25B	110.0
C5—C4—C3	118.92 (15)	C5—C25—H25B	110.0
C5—C4—C24	120.84 (15)	H25A—C25—H25B	108.4
C3—C4—C24	120.23 (15)	O5—C26—C27	124.33 (15)
C4—C5—C6	120.92 (14)	O5—C26—C31	115.51 (14)
C4—C5—C25	120.82 (15)	C27—C26—C31	120.16 (15)
C6—C5—C25	118.23 (14)	C28—C27—C26	118.49 (16)
C1—C6—C5	119.42 (15)	C28—C27—H27	120.8
C1—C6—C33	121.30 (15)	C26—C27—H27	120.8
C5—C6—C33	119.28 (15)	C29—C28—C27	121.87 (16)
O1—C7—C1	106.47 (13)	C29—C28—H28	119.1
O1—C7—H7A	110.4	C27—C28—H28	119.1
C1—C7—H7A	110.4	C28—C29—C30	118.84 (16)
O1—C7—H7B	110.4	C28—C29—C32	120.75 (17)
C1—C7—H7B	110.4	C30—C29—C32	120.40 (17)
H7A—C7—H7B	108.6	C31—C30—C29	120.46 (17)
O1—C8—C9	124.31 (15)	C31—C30—H30	119.8
O1—C8—C13	115.36 (15)	C29—C30—H30	119.8
C9—C8—C13	120.32 (16)	C30—C31—C26	120.18 (16)
C10—C9—C8	118.72 (16)	C30—C31—H31	119.9
C10—C9—H9	120.6	C26—C31—H31	119.9
C8—C9—H9	120.6	O6—C32—C29	124.52 (19)
C9—C10—C11	121.49 (16)	O6—C32—H32	117.7
C9—C10—H10	119.3	C29—C32—H32	117.7
C11—C10—H10	119.3	C6—C33—H33A	109.5
C10—C11—C12	119.07 (17)	C6—C33—H33B	109.5
C10—C11—C14	119.51 (17)	H33A—C33—H33B	109.5
C12—C11—C14	121.40 (17)	C6—C33—H33C	109.5
C13—C12—C11	120.05 (17)	H33A—C33—H33C	109.5
C13—C12—H12	120.0	H33B—C33—H33C	109.5
C11—C12—H12	120.0	C35—C34—H34A	109.5
C12—C13—C8	120.34 (17)	C35—C34—H34B	109.5
C12—C13—H13	119.8	H34A—C34—H34B	109.5
C8—C13—H13	119.8	C35—C34—H34C	109.5
O2—C14—C11	125.3 (2)	H34A—C34—H34C	109.5
O2—C14—H14	117.4	H34B—C34—H34C	109.5
C11—C14—H14	117.4	C35—C34—H34D	109.5
C2—C15—H15A	109.5	H34A—C34—H34D	141.1
C2—C15—H15B	109.5	H34B—C34—H34D	56.3
H15A—C15—H15B	109.5	H34C—C34—H34D	56.3
C2—C15—H15C	109.5	C35—C34—H34E	109.5
H15A—C15—H15C	109.5	H34A—C34—H34E	56.3
H15B—C15—H15C	109.5	H34B—C34—H34E	141.1
O3—C16—C3	106.24 (13)	H34C—C34—H34E	56.3
O3—C16—H16A	110.5	H34D—C34—H34E	109.5
C3—C16—H16A	110.5	C35—C34—H34F	109.5
O3—C16—H16B	110.5	H34A—C34—H34F	56.3
C3—C16—H16B	110.5	H34B—C34—H34F	56.3
H16A—C16—H16B	108.7	H34C—C34—H34F	141.1
O3—C17—C22	124.17 (15)	H34D—C34—H34F	109.5
O3—C17—C18	115.28 (14)	H34E—C34—H34F	109.5
C22—C17—C18	120.55 (15)	O7—C35—O8	122.8 (2)
C19—C18—C17	120.16 (16)	O7—C35—C34	125.5 (2)
C19—C18—H18	119.9	O8—C35—C34	111.74 (17)
C17—C18—H18	119.9	O8—C36—C37	109.22 (17)
C18—C19—C20	120.14 (16)	O8—C36—H36A	109.8
C18—C19—H19	119.9	C37—C36—H36A	109.8
C20—C19—H19	119.9	O8—C36—H36B	109.8
C21—C20—C19	118.85 (15)	C37—C36—H36B	109.8
C21—C20—C23	119.27 (16)	H36A—C36—H36B	108.3
C19—C20—C23	121.88 (16)	C36—C37—H37A	109.5
C22—C21—C20	121.86 (16)	C36—C37—H37B	109.5
C22—C21—H21	119.1	H37A—C37—H37B	109.5
C20—C21—H21	119.1	C36—C37—H37C	109.5
C21—C22—C17	118.41 (16)	H37A—C37—H37C	109.5
C21—C22—H22	120.8	H37B—C37—H37C	109.5
C17—C22—H22	120.8	C8—O1—C7	117.88 (12)
O4—C23—C20	126.41 (18)	C17—O3—C16	118.82 (13)
O4—C23—H23	116.8	C26—O5—C25	116.87 (12)
C20—C23—H23	116.8	C35—O8—C36	116.60 (16)
C4—C24—H24A	109.5
C6—C1—C2—C3	3.1 (2)	C4—C3—C16—O3	−93.21 (17)
C7—C1—C2—C3	−178.72 (13)	O3—C17—C18—C19	−178.37 (16)
C6—C1—C2—C15	−176.66 (15)	C22—C17—C18—C19	1.3 (3)
C7—C1—C2—C15	1.5 (2)	C17—C18—C19—C20	0.1 (3)
C1—C2—C3—C4	−2.4 (2)	C18—C19—C20—C21	−1.6 (3)
C15—C2—C3—C4	177.38 (15)	C18—C19—C20—C23	177.78 (18)
C1—C2—C3—C16	−179.90 (14)	C19—C20—C21—C22	1.6 (3)
C15—C2—C3—C16	−0.2 (2)	C23—C20—C21—C22	−177.80 (18)
C2—C3—C4—C5	0.2 (2)	C20—C21—C22—C17	−0.1 (3)
C16—C3—C4—C5	177.67 (14)	O3—C17—C22—C21	178.33 (17)
C2—C3—C4—C24	−178.49 (15)	C18—C17—C22—C21	−1.3 (3)
C16—C3—C4—C24	−1.0 (2)	C21—C20—C23—O4	−179.5 (2)
C3—C4—C5—C6	1.3 (2)	C19—C20—C23—O4	1.2 (3)
C24—C4—C5—C6	179.95 (15)	C4—C5—C25—O5	−111.81 (16)
C3—C4—C5—C25	−176.50 (14)	C6—C5—C25—O5	70.38 (18)
C24—C4—C5—C25	2.2 (2)	O5—C26—C27—C28	179.78 (17)
C2—C1—C6—C5	−1.6 (2)	C31—C26—C27—C28	−0.8 (3)
C7—C1—C6—C5	−179.82 (14)	C26—C27—C28—C29	1.0 (3)
C2—C1—C6—C33	177.78 (15)	C27—C28—C29—C30	−0.6 (3)
C7—C1—C6—C33	−0.4 (2)	C27—C28—C29—C32	−179.77 (18)
C4—C5—C6—C1	−0.5 (2)	C28—C29—C30—C31	−0.1 (3)
C25—C5—C6—C1	177.26 (14)	C32—C29—C30—C31	179.09 (18)
C4—C5—C6—C33	−179.98 (15)	C29—C30—C31—C26	0.3 (3)
C25—C5—C6—C33	−2.2 (2)	O5—C26—C31—C30	179.61 (17)
C2—C1—C7—O1	−84.96 (18)	C27—C26—C31—C30	0.2 (3)
C6—C1—C7—O1	93.23 (18)	C28—C29—C32—O6	179.6 (2)
O1—C8—C9—C10	179.55 (16)	C30—C29—C32—O6	0.5 (3)
C13—C8—C9—C10	−0.4 (3)	C9—C8—O1—C7	−2.3 (2)
C8—C9—C10—C11	−0.3 (3)	C13—C8—O1—C7	177.68 (16)
C9—C10—C11—C12	0.9 (3)	C1—C7—O1—C8	175.86 (14)
C9—C10—C11—C14	179.75 (18)	C22—C17—O3—C16	−8.9 (3)
C10—C11—C12—C13	−0.7 (3)	C18—C17—O3—C16	170.78 (16)
C14—C11—C12—C13	−179.56 (19)	C3—C16—O3—C17	−150.11 (15)
C11—C12—C13—C8	0.0 (3)	C27—C26—O5—C25	−9.9 (2)
O1—C8—C13—C12	−179.39 (18)	C31—C26—O5—C25	170.69 (15)
C9—C8—C13—C12	0.6 (3)	C5—C25—O5—C26	−170.68 (14)
C10—C11—C14—O2	−177.3 (2)	O7—C35—O8—C36	1.2 (3)
C12—C11—C14—O2	1.5 (3)	C34—C35—O8—C36	−177.88 (18)
C2—C3—C16—O3	84.32 (17)	C37—C36—O8—C35	−167.76 (18)