Synthesis and structure of, and bonding in some derivatives of 2,6,9,10-tetraoxatricyclo[3.3.1.1^3,8]decane

Five derivatives of 2,6,9,10-tetraoxatricyclo[3.3.1.1^3,8]decane were synthesized and their molecular structures in the solid state were determined by means of X-ray diffraction analysis. In addition, the structures of all the molecules were optimized at different levels of computational quantum chemistry (HF/6-31G*, B3LYP/6-31G*). Experimentally determined bond lengths were compared with their calculated counterparts, and striking differences between the Hartree-Fock (HF) results and the experimental data could be traced back to the lack of correlation energy in the geometry optimizations. Two of the compounds under consideration are diastereomers and their relative stability was not only calculated with a conventional ab initio method (ZPE+MP2/6-31G*//HF/6-31G*), but also within the framework of density functional theory (B3LYP/6-31G*). In some of the calculations the influence of the solvent was included in single point calculations by means of an electrostatic model. Moreover, combining experimental as well as computational results, the exclusive axial orientation of a Cl atom in one of the compounds could be explained by an interplay of kinetic and energetic effects.

Computing details

Data reduction: Xtal ADDREF for (3); Xtal DIFDAT SORTRF ADDREF for (4), 5ax, 5eq, (6). For all compounds, program(s) used to solve structure: Xtal; program(s) used to refine structure: Xtal CRYLSQ; molecular graphics: Xtal; software used to prepare material for publication: Xtal BONDLA CIFIO.

Figures

(3)

Crystal data

C14H19ClO8	F(000) = 736
Mr = 350.75	Dx = 1.424 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 8.117 (1) Å	θ = 29.1–53.4°
b = 8.5598 (7) Å	µ = 2.43 mm^−1
c = 23.786 (3) Å	T = 293 K
β = 98.19 (5)°	Irregular, colourless
V = 1635.8 (4) Å^3	0.40 × 0.40 × 0.20 mm
Z = 4

Data collection

CAD4 diffractometer	3203 reflections with F^2 > .00 sig(F^2)
Radiation source: fine-focus sealed tu	Rint = 0.013
Graphite monochromator	θmax = 72.6°, θmin = 3.8°
ω/2θ scans	h = −10→8
Absorption correction: empirical (using intensity measurements) A.C.T.North, D.C.Phillips, F.S.Matthews, Acta Cryst. A24, 351-359 (1968). The Tmin/Tmax values give below are relative values.	k = 0→10
Tmin = 0.810, Tmax = 0.999	l = 0→27
3274 measured reflections	3 standard reflections every 400 reflections
3203 independent reflections	intensity decay: 9%

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	0 constraints
R[F^2 > 2σ(F^2)] = 0.058	All H-atom parameters refined
wR(F^2) = 0.091	w = 1/[3σ^2(F^2)]
S = 1.03	(Δ/σ)max = 0.0004
3203 reflections	Δρmax = 0.41 e Å^−3
284 parameters	Δρmin = −0.50 e Å^−3

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

	x	y	z	Uiso*/Ueq
Cl	0.52269 (9)	−0.03693 (8)	0.34939 (3)	0.0680 (4)
O4	0.39775 (19)	0.39401 (18)	0.39468 (7)	0.0425 (9)
O7	0.3326 (2)	0.08834 (19)	0.41908 (7)	0.0477 (9)
O8	0.1841 (2)	0.12900 (18)	0.32881 (7)	0.0447 (9)
O10	0.1954 (2)	0.39719 (18)	0.31983 (7)	0.0440 (9)
O13	0.2685 (2)	0.3484 (2)	0.49694 (7)	0.0605 (11)
O15	0.0029 (3)	0.2817 (3)	0.49171 (8)	0.0851 (15)
O20	0.5636 (2)	0.4769 (2)	0.31188 (9)	0.0657 (12)
O21	0.7148 (3)	0.2606 (3)	0.32754 (10)	0.0815 (15)
C1	0.1738 (3)	0.1299 (3)	0.38761 (10)	0.0404 (12)
C2	0.1217 (3)	0.2947 (3)	0.40576 (10)	0.0393 (12)
C3	0.2220 (3)	0.4207 (3)	0.37970 (10)	0.0402 (12)
C5	0.4417 (3)	0.2740 (3)	0.35783 (10)	0.0412 (12)
C6	0.4744 (3)	0.1269 (3)	0.39502 (11)	0.0471 (13)
C9	0.2807 (3)	0.2562 (3)	0.31257 (10)	0.0422 (12)
C11	0.1820 (5)	0.5871 (3)	0.39321 (15)	0.0551 (17)
C12	0.1226 (3)	0.3065 (3)	0.46887 (11)	0.0462 (14)
C14	0.2786 (5)	0.3656 (5)	0.55775 (13)	0.069 (2)
C16	0.0523 (4)	0.0042 (4)	0.39858 (17)	0.0577 (18)
C17	0.3000 (5)	0.2332 (4)	0.25155 (12)	0.0552 (17)
C18	0.6151 (4)	0.1415 (4)	0.44374 (15)	0.0620 (19)
C19	0.5913 (3)	0.3327 (3)	0.33090 (12)	0.0526 (15)
C22	0.6882 (7)	0.5451 (7)	0.2807 (3)	0.092 (3)
H2	0.011 (3)	0.304 (2)	0.3893 (9)	0.037 (6)*
H111	0.216 (3)	0.605 (3)	0.4341 (13)	0.081 (10)*
H112	0.262 (4)	0.652 (3)	0.3797 (12)	0.079 (10)*
H113	0.066 (4)	0.607 (4)	0.3729 (13)	0.089 (11)*
H141	0.248 (4)	0.268 (4)	0.5761 (14)	0.112 (14)*
H142	0.404 (6)	0.404 (5)	0.5700 (18)	0.18 (2)*
H143	0.211 (4)	0.454 (4)	0.5658 (16)	0.122 (15)*
H161	−0.059 (3)	0.031 (3)	0.3790 (12)	0.075 (10)*
H162	0.050 (4)	−0.005 (3)	0.4400 (13)	0.084 (11)*
H163	0.086 (4)	−0.083 (3)	0.3860 (12)	0.074 (10)*
H171	0.380 (4)	0.142 (4)	0.2455 (12)	0.089 (10)*
H172	0.196 (4)	0.215 (3)	0.2314 (12)	0.080 (11)*
H173	0.350 (3)	0.315 (3)	0.2367 (11)	0.067 (9)*
H181	0.582 (3)	0.234 (3)	0.4663 (11)	0.070 (9)*
H182	0.713 (4)	0.164 (4)	0.4283 (13)	0.089 (11)*
H183	0.619 (4)	0.044 (4)	0.4676 (13)	0.089 (11)*
H221	0.708 (6)	0.477 (6)	0.252 (2)	0.19 (3)*
H222	0.771 (7)	0.569 (6)	0.307 (2)	0.21 (3)*
H223	0.642 (7)	0.617 (7)	0.256 (2)	0.21 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl	0.0726 (5)	0.0474 (4)	0.0850 (6)	0.0187 (4)	0.0150 (4)	−0.0056 (4)
O4	0.0435 (9)	0.0383 (9)	0.0460 (10)	−0.0016 (7)	0.0077 (8)	−0.0067 (8)
O7	0.0448 (9)	0.0421 (10)	0.0559 (11)	0.0060 (8)	0.0061 (8)	0.0113 (8)
O8	0.0521 (10)	0.0347 (9)	0.0463 (10)	−0.0017 (8)	0.0033 (8)	−0.0042 (8)
O10	0.0546 (10)	0.0365 (9)	0.0410 (9)	0.0084 (8)	0.0067 (8)	0.0027 (7)
O13	0.0540 (11)	0.0832 (14)	0.0433 (11)	−0.0074 (10)	0.0037 (9)	−0.0085 (10)
O15	0.0628 (13)	0.135 (2)	0.0612 (14)	−0.0290 (14)	0.0227 (11)	−0.0098 (14)
O20	0.0661 (13)	0.0568 (12)	0.0803 (15)	−0.0046 (10)	0.0316 (11)	0.0148 (11)
O21	0.0601 (13)	0.0859 (16)	0.1055 (18)	0.0147 (12)	0.0361 (13)	0.0164 (14)
C1	0.0415 (13)	0.0351 (12)	0.0440 (14)	0.0005 (10)	0.0040 (11)	0.0025 (11)
C2	0.0412 (13)	0.0357 (12)	0.0406 (13)	0.0019 (11)	0.0045 (11)	0.0018 (11)
C3	0.0483 (13)	0.0339 (12)	0.0390 (13)	0.0037 (10)	0.0083 (11)	−0.0012 (10)
C5	0.0412 (13)	0.0371 (13)	0.0463 (14)	0.0013 (10)	0.0090 (11)	−0.0035 (11)
C6	0.0416 (13)	0.0436 (14)	0.0568 (16)	0.0057 (11)	0.0095 (12)	0.0015 (12)
C9	0.0510 (14)	0.0327 (12)	0.0429 (13)	0.0030 (11)	0.0062 (11)	−0.0020 (11)
C11	0.069 (2)	0.0333 (14)	0.066 (2)	0.0043 (14)	0.0190 (17)	−0.0025 (14)
C12	0.0501 (15)	0.0409 (13)	0.0485 (15)	−0.0019 (11)	0.0101 (12)	0.0002 (12)
C14	0.084 (3)	0.085 (3)	0.0374 (16)	−0.006 (2)	0.0067 (16)	−0.0061 (17)
C16	0.0592 (19)	0.0381 (16)	0.078 (2)	−0.0067 (13)	0.0166 (18)	0.0015 (15)
C17	0.069 (2)	0.0566 (18)	0.0406 (15)	−0.0001 (16)	0.0107 (15)	−0.0052 (14)
C18	0.0466 (17)	0.073 (2)	0.064 (2)	0.0074 (16)	0.0012 (15)	0.0089 (18)
C19	0.0516 (16)	0.0524 (16)	0.0552 (17)	−0.0022 (13)	0.0118 (13)	−0.0015 (13)
C22	0.087 (3)	0.102 (3)	0.095 (3)	−0.025 (3)	0.042 (3)	0.025 (3)

Geometric parameters (Å, º)

Cl—C6	1.849 (3)	C5—C6	1.540 (3)
O4—C5	1.428 (3)	C5—C9	1.577 (3)
O4—C3	1.438 (3)	C6—C18	1.512 (4)
O7—C6	1.396 (3)	C9—C17	1.495 (4)
O7—C1	1.440 (3)	C11—H112	0.94 (3)
O8—C1	1.413 (3)	C11—H111	0.98 (3)
O8—C9	1.427 (3)	C11—H113	1.01 (3)
O10—C9	1.414 (3)	C14—H143	0.97 (4)
O10—C3	1.424 (3)	C14—H141	0.99 (3)
O13—C12	1.323 (3)	C14—H142	1.07 (4)
O13—C14	1.444 (4)	C16—H163	0.86 (3)
O15—C12	1.198 (4)	C16—H161	0.98 (3)
O20—C19	1.323 (3)	C16—H162	0.99 (3)
O20—C22	1.459 (6)	C17—H173	0.91 (3)
O21—C19	1.190 (4)	C17—H172	0.92 (3)
C1—C16	1.507 (4)	C17—H171	1.04 (3)
C1—C2	1.552 (3)	C18—H182	0.94 (3)
C2—H2	0.93 (2)	C18—H183	1.00 (3)
C2—C12	1.503 (4)	C18—H181	1.01 (3)
C2—C3	1.534 (3)	C22—H222	0.87 (5)
C3—C11	1.506 (4)	C22—H223	0.90 (6)
C5—C19	1.536 (4)	C22—H221	0.92 (5)
H221···H223	1.32 (8)	Cl···H161	3.42 (3)
H111···H112	1.46 (4)	H2···H222	3.42 (6)
H172···H173	1.51 (4)	O15···H161	3.42 (3)
H162···H163	1.51 (4)	C5···H183	3.42 (3)
H171···H173	1.51 (4)	C22···H172^i	3.42 (3)
H161···H163	1.52 (4)	C18···H183	3.42 (3)
H222···H223	1.54 (7)	C12···H113	3.42 (3)
H221···H222	1.54 (7)	H171···H173	3.43 (4)
H181···H182	1.61 (4)	C11···H172^i	3.43 (3)
H171···H172	1.61 (4)	O20···C3	3.434 (3)
H142···H143	1.61 (6)	O4···H143	3.44 (4)
H112···H113	1.62 (4)	O21···H173	3.44 (2)
H161···H162	1.62 (4)	H142···H222	3.44 (7)
H141···H143	1.64 (5)	C3···C19	3.448 (4)
H182···H183	1.65 (4)	C3···H142	3.45 (4)
H181···H183	1.65 (4)	C14···H113	3.46 (3)
H141···H142	1.74 (6)	O20···C14	3.456 (4)
H111···H113	1.76 (4)	O20···H112	3.46 (3)
O20···H222	1.88 (5)	C16···H113	3.46 (3)
C1···H163	1.95 (3)	C17···H113	3.47 (3)
O20···H221	1.96 (5)	H113···H172^i	3.48 (5)
O20···H223	1.97 (6)	O15···H113	3.48 (3)
O13···H142	1.97 (4)	C16···H141	3.48 (4)
C12···H2	1.98 (2)	C11···H143	3.48 (4)
O13···H143	1.99 (4)	H173···H223	3.49 (6)
C9···H172	1.99 (3)	Cl···H221	3.49 (5)
C1···H2	2.00 (2)	O15···C11	3.489 (4)
C6···H182	2.01 (3)	O21···C9	3.491 (3)
C3···H112	2.01 (3)	C19···H2	3.50 (2)
C6···H181	2.01 (3)	O20···H171	3.50 (3)
C3···H113	2.02 (3)	H111···H143	3.50 (5)
C3···H2	2.03 (2)	O21···H223	3.51 (6)
C9···H173	2.03 (3)	O21···H143	3.51 (4)
O13···H141	2.03 (3)	C16···H112	3.52 (3)
C3···H111	2.04 (3)	C3···H171^i	3.53 (3)
C1···H161	2.06 (3)	O15···H163	3.53 (3)
C1···H162	2.06 (3)	C6···H171	3.53 (3)
C6···H183	2.07 (3)	H172···H173	3.54 (4)
C9···H171	2.13 (3)	Cl···H112	3.54 (3)
O13···O15	2.216 (3)	O10···C6	3.539 (3)
O20···O21	2.223 (3)	C12···H182	3.55 (3)
C3···C9	2.231 (3)	C22···H113	3.55 (3)
O4···O10	2.244 (2)	O13···H183	3.55 (3)
C3···C5	2.300 (3)	C14···H111	3.56 (3)
O8···O10	2.309 (2)	O21···C2	3.564 (3)
O10···C5	2.326 (3)	C9···C11	3.576 (4)
O7···C18	2.330 (4)	C3···C17	3.580 (4)
O7···O8	2.334 (2)	Cl···C17	3.582 (3)
O20···C5	2.345 (3)	C5···C11	3.583 (4)
O8···C16	2.354 (4)	H161···H183	3.59 (4)
C1···C9	2.356 (4)	C2···H143	3.59 (4)
O8···C17	2.356 (4)	O21···C17	3.595 (4)
C12···C14	2.359 (4)	C6···C16	3.596 (4)
O4···C9	2.362 (3)	Cl···H181	3.60 (3)
O13···C2	2.366 (3)	C6···H163	3.61 (3)
O4···C6	2.369 (3)	O21···H222	3.61 (5)
C19···C22	2.370 (7)	O15···C3	3.609 (3)
O7···C16	2.370 (4)	H111···H162	3.61 (4)
O10···C2	2.378 (3)	O7···O10	3.613 (2)
O15···C2	2.384 (3)	O20···H141	3.61 (3)
O10···C17	2.392 (4)	C2···H182	3.61 (3)
O4···C19	2.393 (3)	C6···C17	3.619 (4)
O10···C11	2.399 (4)	C5···H112	3.62 (3)
O4···C11	2.405 (4)	O21···H181	3.62 (3)
O7···C5	2.408 (3)	C22···H143	3.63 (4)
H2···H161	2.41 (4)	H171···H221	3.63 (6)
C1···C6	2.421 (3)	O15···H111	3.63 (3)
O8···C2	2.425 (3)	Cl···H173	3.63 (3)
O21···C5	2.430 (3)	C11···H173^i	3.63 (3)
O4···H142	2.43 (4)	H2···H112	3.63 (4)
O8···C5	2.445 (3)	C1···C17	3.640 (4)
O4···C2	2.446 (3)	C1···C18	3.642 (4)
O8···H172	2.45 (3)	O15···C16	3.652 (4)
O7···C2	2.449 (3)	O4···C17	3.653 (3)
O15···H2	2.45 (2)	C9···C16	3.655 (4)
O8···H163	2.47 (3)	O15···H142	3.66 (4)
O7···H183	2.47 (3)	C11···H222	3.66 (5)
O4···H112	2.48 (3)	O13···C6	3.663 (3)
O7···H181	2.50 (3)	O13···H162	3.67 (3)
O10···H113	2.51 (3)	C1···H181	3.67 (3)
O4···H181	2.51 (3)	C14···H183	3.68 (3)
O7···H163	2.51 (3)	C14···H181	3.68 (3)
O10···H2	2.51 (2)	Cl···H142	3.68 (4)
C19···H221	2.53 (5)	C14···H181	3.68 (3)
C1···C3	2.531 (3)	C11···C17^i	3.686 (5)
C1···C12	2.534 (4)	C3···H181	3.69 (3)
O21···H182	2.54 (3)	C5···H2	3.69 (2)
O7···H162	2.55 (3)	C19···H223	3.69 (6)
C2···C16	2.550 (4)	O13···C18	3.697 (4)
O21···H221	2.57 (5)	O15···H183	3.70 (3)
C3···C12	2.567 (4)	C17···H223	3.70 (5)
C5···C18	2.574 (4)	C2···C14	3.708 (4)
C2···C11	2.576 (4)	C5···C22	3.715 (7)
C9···C19	2.581 (4)	O8···H221	3.72 (5)
C6···C9	2.581 (3)	O20···C6	3.717 (3)
O10···H173	2.59 (3)	O10···H222	3.72 (5)
O8···H161	2.59 (3)	C16···H111	3.72 (3)
O4···H111	2.59 (3)	O21···C16	3.722 (4)
H161···H182	2.59 (4)	C18···H141	3.73 (3)
C6···C19	2.597 (4)	C11···C16	3.730 (4)
C16···H2	2.60 (2)	C18···H111	3.73 (3)
C19···H222	2.61 (6)	O8···C19	3.731 (3)
O15···H141	2.62 (3)	C22···H141	3.73 (3)
O10···H172	2.62 (3)	C22···H171	3.74 (3)
O10···H112	2.62 (3)	C14···C19	3.742 (5)
O8···H2	2.62 (2)	C9···H171^i	3.75 (3)
C12···H141	2.63 (3)	C6···H183	3.75 (3)
O10···H171^i	2.63 (3)	C18···H143	3.75 (4)
O4···O20	2.636 (3)	O10···C12	3.757 (3)
C12···H143	2.64 (4)	C22···H142	3.76 (4)
O8···C6	2.641 (3)	O15···O15	3.758 (4)
O15···C14	2.644 (4)	O8···C12	3.759 (3)
C5···C17	2.647 (4)	C18···H162	3.76 (3)
Cl···O7	2.647 (2)	C9···H112	3.76 (3)
O13···H111	2.65 (3)	C12···H162	3.76 (3)
O21···H2	2.66 (2)	O8···C22	3.767 (6)
H2···H113	2.66 (4)	O7···O15	3.769 (3)
O21···C22	2.674 (7)	C9···H223	3.77 (5)
H113···H163	2.68 (4)	C18···H162	3.78 (3)
C1···C5	2.681 (3)	C3···H172^i	3.78 (3)
O20···H173	2.69 (3)	O4···H183	3.78 (3)
C5···H181	2.69 (3)	O7···C18	3.782 (4)
H113···H222	2.69 (6)	O4···H173	3.78 (3)
H112···H163	2.69 (4)	C16···H173	3.78 (3)
O15···H143	2.70 (3)	C12···H181	3.79 (3)
O8···H171	2.72 (3)	Cl···H163	3.79 (3)
C2···H161	2.72 (3)	Cl···C14	3.792 (4)
O21···H223	2.73 (6)	C22···H161^i	3.80 (3)
Cl···C18	2.730 (4)	O7···C19	3.800 (3)
C5···H182	2.74 (3)	C17···H171^i	3.80 (3)
H183···H183	2.74 (4)	C17···H173	3.80 (3)
O21···H222	2.74 (5)	C3···H173	3.80 (3)
C2···C9	2.739 (4)	O13···H112	3.81 (3)
O4···O7	2.748 (2)	O20···C17^i	3.812 (4)
Cl···C5	2.756 (2)	C1···H172	3.82 (3)
C19···H173	2.76 (2)	C14···H112	3.82 (3)
H112···H172^i	2.76 (4)	O15···C12	3.822 (4)
O8···C3	2.773 (3)	O10···H173^i	3.82 (3)
C2···H162	2.78 (3)	O13···C5	3.828 (3)
C11···H2	2.79 (2)	Cl···C17	3.835 (3)
C19···H182	2.79 (3)	C19···H172	3.84 (3)
O15···H182	2.80 (3)	O13···H181	3.84 (3)
O15···H162	2.80 (3)	C2···H181	3.84 (3)
C12···H162	2.80 (3)	C9···H163	3.84 (3)
C2···H113	2.80 (3)	C9···H113	3.85 (3)
O4···O13	2.810 (2)	C12···H183	3.85 (3)
C2···H111	2.82 (3)	C11···H162	3.86 (3)
C12···H111	2.82 (3)	C17···H163^i	3.86 (3)
O10···C1	2.819 (3)	O13···H113	3.86 (3)
O13···C3	2.829 (3)	C12···H163	3.86 (3)
Cl···H182	2.83 (3)	O15···C14	3.867 (5)
O21···H161	2.84 (3)	C11···H141	3.87 (4)
O15···H111	2.85 (3)	O7···H112	3.87 (3)
H112···H142	2.85 (5)	C3···C16	3.871 (4)
C5···H171	2.88 (3)	O7···H181	3.87 (3)
O7···C9	2.891 (3)	C16···H183	3.87 (3)
O4···C1	2.891 (3)	O8···O20	3.875 (2)
C5···H173	2.89 (3)	C6···C12	3.877 (4)
O7···C12	2.893 (3)	O10···H223	3.88 (5)
Cl···H183	2.89 (3)	C9···H161	3.88 (3)
H113···H143	2.90 (5)	C18···H2	3.89 (2)
O7···H183	2.90 (3)	C19···H161	3.89 (3)
O13···H181	2.91 (3)	O13···O15	3.888 (3)
H2···H162	2.91 (4)	C14···C22	3.889 (7)
H113···H171^i	2.92 (4)	C22···H221	3.89 (5)
O4···C18	2.926 (4)	C5···H143	3.90 (4)
H172···H223	2.93 (6)	O8···C17	3.901 (4)
C11···H163	2.93 (3)	C12···H112	3.90 (3)
O21···C6	2.931 (4)	C1···H183	3.90 (3)
C17···C19	2.934 (4)	C16···H223	3.90 (5)
O15···H162	2.94 (3)	C16···H221	3.91 (5)
C19···H171	2.95 (3)	C12···H111	3.91 (3)
H2···H182	2.96 (4)	C1···H183	3.91 (3)
O20···H142	2.97 (4)	C18···H142	3.91 (4)
O20···C9	2.975 (3)	C17···H221	3.91 (5)
C2···C5	2.987 (4)	Cl···H223	3.91 (6)
O7···O13	2.989 (3)	O13···H142	3.91 (5)
Cl···H171	3.00 (3)	C1···C11	3.916 (4)
O20···H172^i	3.01 (3)	O20···H182	3.92 (3)
H143···H222	3.02 (6)	C6···H162	3.92 (3)
H111···H181	3.02 (4)	C11···H181	3.92 (3)
H2···H143	3.03 (4)	C3···H172	3.92 (3)
H112···H171^i	3.04 (4)	O15···C11	3.925 (4)
H111···H163	3.04 (4)	O20···H171^i	3.93 (3)
O15···H143	3.05 (4)	C5···H221	3.94 (5)
Cl···O21	3.069 (2)	C6···H161	3.95 (3)
Cl···O8	3.0706 (18)	C5···H111	3.95 (3)
C9···H2	3.07 (2)	C9···C18	3.957 (4)
H162···H182	3.07 (4)	O21···C1	3.957 (3)
H162···H162	3.08 (5)	C5···C12	3.963 (4)
C11···C12	3.080 (4)	C1···H223	3.96 (5)
C19···H223	3.08 (6)	O8···O21	3.968 (3)
O8···H223	3.09 (5)	O21···H142	3.97 (4)
O7···C3	3.088 (3)	C22···H2	3.98 (2)
C12···C16	3.089 (4)	C1···H173	3.98 (3)
O13···H2	3.09 (2)	C1···H171	3.98 (3)
Cl···H141	3.10 (3)	O21···H183	3.99 (3)
O8···H173	3.10 (3)	O13···H183	3.99 (3)
O10···O20	3.097 (3)	C14···H2	3.99 (2)
H111···H142	3.11 (5)	O20···C11	3.992 (4)
H112···H173^i	3.12 (4)	C5···H222	3.99 (6)
H141···H183	3.12 (5)	O8···H172	3.99 (3)
C18···C19	3.126 (5)	O20···H172	3.99 (3)
O4···C12	3.128 (3)	O13···C16	4.008 (4)
O7···H182	3.13 (3)	C1···H182	4.01 (3)
H141···H222	3.14 (6)	C2···H143	4.01 (4)
O4···O8	3.136 (2)	Cl···O4	4.0134 (17)
O10···H172^i	3.16 (3)	C3···H222	4.03 (5)
O21···C18	3.158 (4)	C16···C18	4.027 (5)
H163···H173	3.16 (4)	C14···H182	4.04 (3)
H2···H111	3.16 (3)	O4···C22	4.050 (6)
H113···H141	3.16 (5)	C11···C14	4.092 (6)
O8···H173	3.16 (3)	C3···C17^i	4.096 (4)
C17···H112	3.17 (3)	O10···C16	4.098 (4)
O20···C17	3.180 (4)	O10···O21	4.101 (3)
C12···H142	3.18 (4)	C3···C18	4.102 (4)
H173···H221	3.19 (6)	O4···O13	4.106 (2)
O7···H2	3.20 (2)	C17···C22	4.113 (7)
O13···C11	3.203 (4)	O8···C18	4.123 (3)
O21···H221	3.20 (5)	C9···C12	4.125 (4)
O13···C1	3.207 (3)	Cl···H222	4.13 (6)
O8···H162	3.21 (3)	O4···C14	4.136 (4)
H161···H221	3.22 (6)	O7···C14	4.137 (4)
O4···H2	3.22 (2)	C5···C16	4.139 (4)
Cl···H172	3.22 (3)	Cl···H173	4.14 (3)
O7···H161	3.23 (3)	O7···C17	4.146 (3)
H142···H181	3.23 (5)	C2···C17	4.164 (4)
O4···H113	3.23 (3)	Cl···C16	4.165 (4)
Cl···C9	3.230 (2)	Cl···H223	4.17 (6)
O10···H111	3.23 (3)	C5···C14	4.172 (5)
C3···C6	3.231 (3)	Cl···H172	4.17 (3)
O10···C19	3.234 (3)	C2···C18	4.189 (4)
O4···H182	3.24 (3)	O10···O13	4.191 (2)
H141···H161	3.24 (5)	C1···C19	4.198 (4)
H162···H183	3.24 (4)	Cl···O10	4.1979 (18)
C16···H182	3.24 (3)	O21···C14	4.201 (5)
C2···C6	3.246 (4)	Cl···C22	4.201 (6)
Cl···C19	3.253 (3)	C19···C22	4.203 (7)
C19···H142	3.26 (4)	O8···C11	4.211 (3)
O20···H143	3.26 (3)	C3···C14	4.220 (4)
H161···H223	3.26 (6)	O20···C18	4.229 (4)
O21···H171	3.27 (3)	Cl···C22	4.230 (6)
C2···H163	3.27 (3)	C18···C18	4.237 (5)
O15···C1	3.275 (3)	C12···C12	4.238 (4)
H141···H162	3.28 (4)	C17···C22	4.245 (7)
C19···H143	3.29 (4)	O15···O21	4.260 (3)
C11···H171^i	3.30 (3)	C12···C14	4.277 (5)
O10···H171	3.30 (3)	Cl···O20	4.279 (2)
H143···H181	3.30 (5)	O10···C22	4.281 (6)
H113···H173^i	3.31 (4)	C9···C22	4.283 (6)
H171···H222	3.31 (6)	O8···O10	4.287 (2)
O15···C16	3.311 (4)	O7···O21	4.297 (3)
H143···H182	3.32 (5)	Cl···C16	4.306 (3)
H221···H223	3.33 (8)	C14···C18	4.308 (6)
C19···H181	3.34 (3)	C12···C18	4.315 (4)
O10···C17^i	3.343 (4)	O4···O15	4.316 (3)
C14···H222	3.35 (5)	C11···C14	4.319 (5)
O21···C22	3.351 (7)	O8···O20	4.344 (3)
C2···H112	3.35 (3)	O21···C3	4.349 (3)
C11···H142	3.35 (4)	O10···O21	4.354 (3)
H142···H181	3.36 (5)	C17···C17^i	4.355 (5)
H141···H163	3.37 (5)	C17···C17	4.355 (5)
H2···H163	3.37 (4)	C12···C18	4.361 (4)
C18···H161	3.38 (3)	O4···C16	4.368 (4)
C12···H161	3.38 (3)	C14···C16	4.372 (6)
H111···H143	3.39 (5)	C9···C17^i	4.375 (4)
H181···H183	3.39 (4)	O21···C12	4.386 (3)
C5···H142	3.40 (4)	C11···C14	4.386 (5)
C5···H172	3.40 (3)	C11···C19	4.403 (5)
C12···H143	3.40 (4)	C14···C18	4.427 (6)
O4···C14	3.401 (4)	C2···C19	4.430 (4)
Cl···C1	3.409 (3)	Cl···C11	4.462 (3)
O15···C18	3.410 (4)	Cl···O20	4.509 (2)
O15···H181	3.41 (3)	Cl···O10	4.5639 (17)
O4···O21	3.413 (3)	Cl···C9	4.619 (2)
C22···H173	3.42 (3)	Cl···C2	4.658 (3)
C5—O4—C3	106.72 (16)	H112—C11—H111	98 (2)
C6—O7—C1	117.24 (18)	H112—C11—H113	112 (2)
C1—O8—C9	112.09 (17)	H112—C11—C3	108.0 (18)
C9—O10—C3	103.63 (16)	H111—C11—H113	124 (2)
C12—O13—C14	116.9 (2)	H111—C11—C3	108.5 (17)
C19—O20—C22	116.8 (3)	H113—C11—C3	105.6 (18)
O8—C1—O7	109.79 (19)	O15—C12—O13	123.0 (2)
O8—C1—C16	107.4 (2)	O15—C12—C2	123.5 (2)
O8—C1—C2	109.70 (18)	O13—C12—C2	113.5 (2)
O7—C1—C16	107.1 (2)	H143—C14—H141	113 (3)
O7—C1—C2	109.85 (18)	H143—C14—H142	104 (3)
C16—C1—C2	112.9 (2)	H143—C14—O13	109 (2)
H2—C2—C12	106.2 (14)	H141—C14—H142	115 (3)
H2—C2—C3	107.7 (13)	H141—C14—O13	112 (2)
H2—C2—C1	104.5 (13)	H142—C14—O13	103 (2)
C12—C2—C3	115.4 (2)	H163—C16—H161	111 (2)
C12—C2—C1	112.1 (2)	H163—C16—H162	109 (3)
C3—C2—C1	110.2 (2)	H163—C16—C1	108 (2)
O10—C3—O4	103.24 (18)	H161—C16—H162	110 (2)
O10—C3—C11	109.9 (2)	H161—C16—C1	109.5 (17)
O10—C3—C2	106.90 (18)	H162—C16—C1	109.7 (17)
O4—C3—C11	109.5 (2)	H173—C17—H172	111 (2)
O4—C3—C2	110.69 (18)	H173—C17—H171	102 (2)
C11—C3—C2	115.8 (2)	H173—C17—C9	112.9 (17)
O4—C5—C19	107.58 (19)	H172—C17—H171	110 (2)
O4—C5—C6	105.9 (2)	H172—C17—C9	108 (2)
O4—C5—C9	103.51 (18)	H171—C17—C9	112.9 (16)
C19—C5—C6	115.2 (2)	H182—C18—H183	116 (3)
C19—C5—C9	112.0 (2)	H182—C18—H181	111 (2)
C6—C5—C9	111.79 (19)	H182—C18—C6	107.7 (18)
O7—C6—C18	106.4 (2)	H183—C18—H181	110 (2)
O7—C6—C5	110.1 (2)	H183—C18—C6	108.8 (16)
O7—C6—Cl	108.51 (16)	H181—C18—C6	103.8 (14)
C18—C6—C5	115.0 (2)	O21—C19—O20	124.4 (3)
C18—C6—Cl	108.2 (2)	O21—C19—C5	125.6 (3)
C5—C6—Cl	108.46 (18)	O20—C19—C5	110.0 (2)
O10—C9—O8	108.7 (2)	H222—C22—H223	121 (5)
O10—C9—C17	110.6 (2)	H222—C22—H221	118 (5)
O10—C9—C5	101.92 (17)	H222—C22—O20	105 (4)
O8—C9—C17	107.5 (2)	H223—C22—H221	93 (5)
O8—C9—C5	108.83 (18)	H223—C22—O20	111 (4)
C17—C9—C5	119.0 (2)	H221—C22—O20	109 (3)
C5—O4—C3—O10	−34.8 (2)	H2—C2—C3—O10	−57.1 (14)
C5—O4—C3—C2	79.3 (2)	H2—C2—C3—C11	65.7 (14)
C5—O4—C3—C11	−151.8 (2)	C1—C2—C12—O13	88.4 (3)
C3—O4—C5—C6	−107.5 (2)	C1—C2—C12—O15	−92.1 (3)
C3—O4—C5—C9	10.2 (2)	C3—C2—C12—O13	−38.8 (3)
C3—O4—C5—C19	128.88 (19)	C3—C2—C12—O15	140.7 (3)
C6—O7—C1—O8	29.5 (3)	H2—C2—C12—O13	−158.1 (14)
C6—O7—C1—C2	−91.2 (2)	H2—C2—C12—O15	21.4 (14)
C6—O7—C1—C16	145.9 (2)	O4—C3—C11—H111	−59.5 (18)
C1—O7—C6—Cl	−89.0 (2)	O4—C3—C11—H112	45.7 (17)
C1—O7—C6—C5	29.5 (3)	O4—C3—C11—H113	165.6 (19)
C1—O7—C6—C18	154.7 (2)	O10—C3—C11—H111	−172.3 (18)
C9—O8—C1—O7	−71.0 (2)	O10—C3—C11—H112	−67.1 (17)
C9—O8—C1—C2	49.8 (2)	O10—C3—C11—H113	53 (2)
C9—O8—C1—C16	172.9 (2)	C2—C3—C11—H111	66.5 (18)
C1—O8—C9—O10	−66.9 (2)	C2—C3—C11—H112	171.7 (17)
C1—O8—C9—C5	43.4 (2)	C2—C3—C11—H113	−68 (2)
C1—O8—C9—C17	173.4 (2)	O4—C5—C6—Cl	177.39 (14)
C9—O10—C3—O4	47.0 (2)	O4—C5—C6—O7	58.8 (2)
C9—O10—C3—C2	−69.8 (2)	O4—C5—C6—C18	−61.4 (3)
C9—O10—C3—C11	163.8 (2)	C9—C5—C6—Cl	65.4 (2)
C3—O10—C9—O8	75.7 (2)	C9—C5—C6—O7	−53.2 (3)
C3—O10—C9—C5	−39.1 (2)	C9—C5—C6—C18	−173.4 (2)
C3—O10—C9—C17	−166.6 (2)	C19—C5—C6—Cl	−63.9 (2)
C14—O13—C12—O15	−0.7 (4)	C19—C5—C6—O7	177.5 (2)
C14—O13—C12—C2	178.7 (3)	C19—C5—C6—C18	57.3 (3)
C12—O13—C14—H141	58 (2)	O4—C5—C9—O8	−97.0 (2)
C12—O13—C14—H142	−178 (2)	O4—C5—C9—O10	17.7 (2)
C12—O13—C14—H143	−67 (2)	O4—C5—C9—C17	139.5 (2)
C22—O20—C19—O21	5.3 (4)	C6—C5—C9—O8	16.5 (3)
C22—O20—C19—C5	−175.0 (3)	C6—C5—C9—O10	131.2 (2)
C19—O20—C22—H221	52 (3)	C6—C5—C9—C17	−107.0 (3)
C19—O20—C22—H222	−76 (4)	C19—C5—C9—O8	147.4 (2)
C19—O20—C22—H223	152 (4)	C19—C5—C9—O10	−97.9 (2)
O7—C1—C2—C3	75.5 (2)	C19—C5—C9—C17	24.0 (3)
O7—C1—C2—C12	−54.4 (3)	O4—C5—C19—O20	−47.1 (3)
O7—C1—C2—H2	−169.0 (14)	O4—C5—C19—O21	132.6 (3)
O8—C1—C2—C3	−45.3 (2)	C6—C5—C19—O20	−164.9 (2)
O8—C1—C2—C12	−175.21 (19)	C6—C5—C19—O21	14.9 (4)
O8—C1—C2—H2	70.2 (14)	C9—C5—C19—O20	66.0 (3)
C16—C1—C2—C3	−165.1 (2)	C9—C5—C19—O21	−114.3 (3)
C16—C1—C2—C12	65.0 (3)	Cl—C6—C18—H181	178.9 (16)
C16—C1—C2—H2	−49.6 (14)	Cl—C6—C18—H182	62 (2)
O7—C1—C16—H161	177.7 (18)	Cl—C6—C18—H183	−64 (2)
O7—C1—C16—H162	56.8 (18)	O7—C6—C18—H181	−64.6 (17)
O7—C1—C16—H163	−62 (2)	O7—C6—C18—H182	178 (2)
O8—C1—C16—H161	−64.4 (18)	O7—C6—C18—H183	52 (2)
O8—C1—C16—H162	174.7 (18)	C5—C6—C18—H181	57.5 (17)
O8—C1—C16—H163	56 (2)	C5—C6—C18—H182	−60 (2)
C2—C1—C16—H161	56.7 (18)	C5—C6—C18—H183	174 (2)
C2—C1—C16—H162	−64.2 (18)	O8—C9—C17—H171	−72.1 (18)
C2—C1—C16—H163	177 (2)	O8—C9—C17—H172	50 (2)
C1—C2—C3—O4	−55.5 (2)	O8—C9—C17—H173	173.4 (18)
C1—C2—C3—O10	56.3 (2)	O10—C9—C17—H171	169.4 (18)
C1—C2—C3—C11	179.1 (2)	O10—C9—C17—H172	−68 (2)
C12—C2—C3—O4	72.7 (3)	O10—C9—C17—H173	54.9 (18)
C12—C2—C3—O10	−175.6 (2)	C5—C9—C17—H171	52.0 (18)
C12—C2—C3—C11	−52.7 (3)	C5—C9—C17—H172	174 (2)
H2—C2—C3—O4	−168.9 (14)	C5—C9—C17—H173	−62.5 (18)

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

(4)

Crystal data

C15H22O9	F(000) = 736
Mr = 346.33	Dx = 1.346 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54179 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 10.858 (3) Å	θ = 10.2–18.9°
b = 14.1170 (8) Å	µ = 0.96 mm^−1
c = 11.519 (4) Å	T = 293 K
β = 104.508 (10)°	Irregular, colourless
V = 1709.4 (8) Å^3	0.70 × 0.40 × 0.30 mm
Z = 4

Data collection

CAD4 diffractometer	Rint = 0.05
Radiation source: Cu anode	θmax = 72.9°, θmin = 4.2°
Graphite monochromator	h = −13→13
ω/2θ scans	k = 0→17
5250 measured reflections	l = −14→14
3070 independent reflections	3 standard reflections every 400 reflections
3070 reflections with F^2 > .00 sig(F^2)	intensity decay: 2%

Refinement

Refinement on F^2	0 constraints
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.049	w = 1/[3.52σ^2(F^2)]
wR(F^2) = 0.064	(Δ/σ)max = 0.014
S = 1.00	Δρmax = 0.22 e Å^−3
3070 reflections	Δρmin = −0.26 e Å^−3
306 parameters	Extinction correction: Zachariasen, Eq22 p292 "Cryst. Comp." Munksgaard 1970
0 restraints	Extinction coefficient: 12819 (300)

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

	x	y	z	Uiso*/Ueq
C1	0.61867 (16)	0.59383 (12)	0.73642 (16)	0.0410 (8)
C2	0.55643 (16)	0.62774 (12)	0.60703 (16)	0.0407 (9)
C3	0.64992 (15)	0.61591 (11)	0.52765 (15)	0.0378 (8)
O4	0.76710 (10)	0.66296 (8)	0.57926 (10)	0.0387 (6)
C5	0.83809 (15)	0.60217 (11)	0.67071 (14)	0.0358 (8)
C6	0.83776 (15)	0.64780 (12)	0.79286 (15)	0.0391 (8)
O7	0.70913 (10)	0.66195 (8)	0.79660 (10)	0.0404 (6)
O8	0.67856 (10)	0.50520 (8)	0.73011 (10)	0.0410 (6)
C9	0.76029 (15)	0.50722 (12)	0.65149 (15)	0.0375 (8)
O10	0.68539 (10)	0.51847 (8)	0.53235 (10)	0.0397 (6)
C11	0.5993 (2)	0.64663 (16)	0.4007 (2)	0.0492 (11)
C12	0.50307 (18)	0.72644 (14)	0.60173 (17)	0.0499 (10)
O13	0.37777 (13)	0.72275 (11)	0.58906 (16)	0.0822 (10)
C14	0.3131 (4)	0.8139 (3)	0.5785 (6)	0.115 (3)
O15	0.56002 (14)	0.79893 (10)	0.60561 (14)	0.0726 (9)
C16	0.5245 (2)	0.57904 (18)	0.8113 (2)	0.0562 (12)
C17	0.8291 (2)	0.41445 (14)	0.6631 (2)	0.0472 (10)
C18	0.8990 (2)	0.74434 (16)	0.8081 (2)	0.0539 (11)
C19	0.97037 (16)	0.59317 (13)	0.64697 (17)	0.0453 (9)
O20	1.05153 (11)	0.54664 (11)	0.73245 (12)	0.0629 (8)
C22	1.1768 (2)	0.5316 (3)	0.7136 (3)	0.084 (2)
O21	0.99644 (14)	0.62242 (14)	0.56084 (14)	0.0970 (11)
O24	0.89800 (11)	0.58257 (9)	0.88125 (10)	0.0491 (7)
C25	0.8974 (3)	0.6075 (3)	1.0018 (2)	0.0804 (18)
H2	0.4892 (14)	0.5868 (10)	0.5796 (14)	0.033 (4)*
H111	0.5927 (16)	0.7174 (15)	0.3997 (16)	0.065 (6)*
H112	0.6540 (17)	0.6313 (14)	0.3539 (16)	0.064 (6)*
H113	0.520 (2)	0.6137 (14)	0.3644 (17)	0.074 (7)*
H141	0.327 (3)	0.848 (3)	0.647 (3)	0.173 (18)*
H142	0.329 (3)	0.841 (3)	0.511 (3)	0.17 (2)*
H143	0.226 (3)	0.790 (2)	0.563 (3)	0.159 (15)*
H161	0.567 (2)	0.5572 (16)	0.887 (2)	0.091 (9)*
H162	0.4802 (17)	0.6379 (15)	0.8072 (16)	0.065 (6)*
H163	0.4637 (19)	0.5265 (15)	0.7756 (18)	0.072 (7)*
H171	0.8792 (19)	0.4082 (15)	0.740 (2)	0.077 (8)*
H172	0.7692 (15)	0.3613 (13)	0.6493 (15)	0.048 (5)*
H173	0.8848 (17)	0.4088 (13)	0.6070 (17)	0.068 (6)*
H181	0.8799 (16)	0.7723 (13)	0.8808 (17)	0.060 (6)*
H182	0.8618 (19)	0.7806 (16)	0.738 (2)	0.077 (8)*
H183	0.9905 (19)	0.7372 (15)	0.8173 (18)	0.080 (7)*
H211	1.223 (2)	0.498 (2)	0.787 (2)	0.104 (10)*
H212	1.178 (3)	0.493 (3)	0.649 (3)	0.161 (16)*
H213	1.210 (2)	0.595 (2)	0.703 (2)	0.110 (11)*
H251	0.924 (2)	0.5569 (17)	1.046 (2)	0.101 (10)*
H252	0.818 (2)	0.6237 (19)	1.005 (2)	0.108 (10)*
H253	0.948 (3)	0.676 (3)	1.017 (3)	0.180 (17)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0371 (9)	0.0400 (9)	0.0491 (11)	−0.0025 (8)	0.0170 (9)	−0.0050 (8)
C2	0.0316 (9)	0.0385 (9)	0.0506 (12)	−0.0028 (8)	0.0074 (9)	−0.0064 (9)
C3	0.0351 (9)	0.0354 (9)	0.0417 (10)	−0.0014 (7)	0.0072 (8)	−0.0029 (8)
O4	0.0342 (6)	0.0371 (6)	0.0426 (7)	−0.0027 (5)	0.0055 (6)	0.0033 (6)
C5	0.0328 (9)	0.0383 (9)	0.0363 (9)	0.0004 (7)	0.0085 (8)	0.0019 (8)
C6	0.0343 (9)	0.0425 (9)	0.0409 (10)	0.0020 (8)	0.0103 (8)	−0.0019 (8)
O7	0.0343 (6)	0.0426 (7)	0.0453 (7)	−0.0011 (5)	0.0118 (6)	−0.0091 (6)
O8	0.0414 (6)	0.0364 (6)	0.0498 (7)	−0.0008 (5)	0.0202 (6)	0.0006 (5)
C9	0.0377 (9)	0.0376 (9)	0.0398 (10)	0.0000 (7)	0.0144 (8)	−0.0008 (8)
O10	0.0406 (7)	0.0364 (6)	0.0402 (7)	0.0004 (5)	0.0068 (6)	−0.0052 (5)
C11	0.0499 (12)	0.0505 (12)	0.0445 (12)	0.0018 (10)	0.0067 (11)	−0.0002 (10)
C12	0.0475 (11)	0.0487 (11)	0.0510 (12)	0.0076 (10)	0.0078 (10)	−0.0088 (10)
O13	0.0437 (8)	0.0723 (10)	0.1259 (14)	0.0169 (8)	0.0122 (9)	−0.0282 (10)
C14	0.080 (2)	0.100 (3)	0.157 (4)	0.050 (2)	0.013 (3)	−0.035 (3)
O15	0.0737 (10)	0.0450 (8)	0.0967 (12)	0.0065 (7)	0.0170 (9)	0.0011 (8)
C16	0.0491 (12)	0.0610 (14)	0.0675 (16)	−0.0027 (12)	0.0316 (13)	−0.0024 (13)
C17	0.0499 (12)	0.0392 (10)	0.0550 (14)	0.0073 (9)	0.0182 (12)	0.0013 (10)
C18	0.0474 (12)	0.0524 (12)	0.0605 (15)	−0.0122 (10)	0.0111 (12)	−0.0129 (12)
C19	0.0376 (9)	0.0518 (10)	0.0491 (11)	0.0017 (9)	0.0158 (9)	0.0031 (9)
O20	0.0346 (7)	0.1013 (11)	0.0543 (8)	0.0159 (7)	0.0137 (7)	0.0166 (8)
C22	0.0400 (12)	0.124 (3)	0.092 (2)	0.0232 (16)	0.0261 (15)	0.021 (2)
O21	0.0636 (9)	0.1543 (17)	0.0884 (12)	0.0413 (10)	0.0480 (9)	0.0659 (12)
O24	0.0507 (8)	0.0598 (8)	0.0359 (7)	0.0124 (6)	0.0094 (6)	0.0019 (6)
C25	0.098 (2)	0.105 (2)	0.0405 (14)	0.038 (2)	0.0220 (15)	0.0090 (15)

Geometric parameters (Å, º)

C1—O8	1.420 (2)	C12—O13	1.332 (2)
C1—O7	1.424 (2)	O13—C14	1.457 (4)
C1—C16	1.509 (3)	C14—H141	0.91 (4)
C1—C2	1.550 (2)	C14—H142	0.93 (4)
C2—H2	0.923 (15)	C14—H143	0.97 (3)
C2—C12	1.504 (3)	C16—H161	0.93 (2)
C2—C3	1.536 (3)	C16—H162	0.96 (2)
C3—O10	1.426 (2)	C16—H163	1.01 (2)
C3—O4	1.4263 (19)	C17—H171	0.92 (2)
C3—C11	1.492 (3)	C17—H172	0.980 (18)
O4—C5	1.4260 (18)	C17—H173	0.99 (2)
C5—C19	1.533 (3)	C18—H182	0.96 (2)
C5—C6	1.548 (2)	C18—H183	0.98 (2)
C5—C9	1.570 (2)	C18—H181	0.99 (2)
C6—O24	1.407 (2)	C19—O21	1.173 (3)
C6—O7	1.422 (2)	C19—O20	1.320 (2)
C6—C18	1.508 (3)	O20—C22	1.446 (3)
O8—C9	1.418 (2)	C22—H212	0.93 (4)
C9—O10	1.418 (2)	C22—H213	0.98 (3)
C9—C17	1.497 (3)	C22—H211	0.99 (2)
C11—H112	0.92 (2)	O24—C25	1.434 (3)
C11—H113	0.97 (2)	C25—H251	0.88 (2)
C11—H111	1.00 (2)	C25—H252	0.91 (3)
C12—O15	1.191 (2)	C25—H253	1.11 (4)
H251···H252	1.48 (3)	H173···H182	3.40 (3)
H112···H113	1.51 (3)	C18···O21	3.405 (3)
H141···H143	1.51 (4)	C11···O15	3.406 (3)
H171···H172	1.53 (2)	C2···O10	3.409 (2)
H161···H163	1.54 (3)	C16···H211	3.41 (3)
H211···H212	1.54 (4)	H142···H211	3.41 (4)
H111···H112	1.54 (3)	C9···O21	3.413 (3)
H171···H173	1.55 (3)	H2···H172	3.41 (2)
H142···H143	1.57 (5)	C12···H111	3.418 (18)
H212···H213	1.58 (4)	C3···C19	3.421 (2)
H252···H253	1.58 (4)	O21···H183	3.42 (2)
H141···H142	1.58 (5)	H142···H172	3.42 (4)
H182···H183	1.59 (3)	O21···H143	3.44 (3)
H172···H173	1.60 (3)	C3···H212	3.44 (4)
H161···H162	1.61 (3)	O15···H162	3.445 (18)
H181···H182	1.61 (3)	H2···H161	3.45 (3)
H162···H163	1.61 (3)	H182···H253	3.45 (4)
H181···H183	1.63 (3)	H143···H172	3.45 (4)
H211···H213	1.66 (4)	H173···H213	3.46 (3)
H111···H113	1.66 (3)	C11···H2	3.456 (15)
H251···H253	1.75 (5)	C16···H252	3.46 (2)
O13···H143	1.86 (3)	C9···H113	3.46 (2)
O24···H251	1.88 (3)	O15···H252	3.46 (3)
O13···H142	1.91 (4)	C22···H251	3.46 (3)
O20···H211	1.94 (2)	H143···H173	3.46 (4)
O24···H252	1.94 (3)	C18···O20	3.466 (3)
O20···H213	1.96 (3)	O8···C14	3.472 (5)
C1···H162	1.98 (2)	C5···H172	3.477 (19)
C12···H2	1.988 (15)	C18···H171	3.48 (2)
C1···H2	1.994 (14)	C6···H171	3.48 (2)
C9···H171	2.00 (2)	O13···H163	3.49 (2)
C6···H182	2.02 (2)	O15···H162	3.51 (2)
C1···H161	2.02 (3)	C9···H141	3.52 (4)
O20···H212	2.02 (4)	O15···H163	3.53 (2)
O24···H253	2.02 (3)	O24···C25	3.528 (4)
O13···H141	2.02 (4)	C19···H181	3.530 (18)
C6···H181	2.023 (19)	C14···H172	3.53 (2)
C3···H2	2.024 (17)	O15···H143	3.53 (3)
C3···H112	2.02 (2)	C22···H162	3.533 (19)
C3···H111	2.038 (19)	O7···H251	3.54 (2)
C6···H183	2.05 (2)	C6···O21	3.542 (3)
C3···H113	2.047 (17)	C3···O13	3.543 (2)
C9···H172	2.063 (19)	C2···H113	3.54 (2)
H181···H253	2.07 (4)	C9···H2	3.546 (14)
C1···H163	2.08 (2)	C6···O10	3.548 (2)
C9···H173	2.09 (2)	C12···H163	3.55 (2)
O20···O21	2.195 (2)	H142···H161	3.55 (5)
O13···O15	2.218 (2)	O4···O20	3.5522 (17)
C3···C9	2.229 (2)	C22···H173	3.552 (18)
O4···O10	2.2359 (15)	H181···H251	3.55 (3)
O13···H2	2.286 (15)	C14···H172	3.554 (18)
C3···C5	2.289 (2)	C14···H171	3.56 (2)
O8···O10	2.3053 (19)	H2···H112	3.56 (3)
C5···O10	2.3155 (18)	O21···H211	3.56 (2)
C2···O13	2.325 (2)	C19···H253	3.57 (4)
O7···O24	2.3259 (16)	O8···H252	3.57 (2)
O7···O8	2.3379 (15)	O10···H213	3.57 (3)
O7···C18	2.342 (3)	O10···H163	3.57 (2)
C19···C22	2.347 (3)	C9···C11	3.570 (3)
O8···C17	2.354 (3)	C5···C11	3.571 (3)
O8···C16	2.355 (3)	C25···H161	3.57 (2)
O4···C9	2.358 (2)	O13···H111	3.57 (2)
C1···C9	2.360 (3)	H142···H213	3.57 (4)
C12···C14	2.362 (5)	H113···H162	3.57 (3)
O4···C19	2.364 (2)	C12···H112	3.574 (18)
O7···C16	2.364 (3)	O21···H182	3.57 (2)
C5···O24	2.364 (2)	C3···C17	3.576 (3)
C5···O20	2.380 (2)	H183···H252	3.58 (4)
C2···O10	2.384 (2)	H183···H253	3.58 (4)
O10···C17	2.384 (2)	O4···H212	3.59 (4)
O4···C11	2.393 (2)	O10···C22	3.590 (4)
C5···O21	2.394 (3)	C6···C16	3.595 (3)
O10···C11	2.395 (2)	C19···H212	3.60 (3)
O4···C6	2.396 (2)	O4···O24	3.5961 (18)
C6···C25	2.398 (3)	C17···O21	3.600 (3)
C5···O7	2.407 (2)	C11···H141	3.60 (3)
C2···O8	2.412 (2)	C6···C17	3.609 (3)
C2···O15	2.417 (2)	H183···H213	3.61 (4)
C1···C6	2.426 (2)	O7···O10	3.6112 (18)
O7···H181	2.430 (17)	C6···H161	3.61 (3)
C18···O24	2.435 (3)	C16···H141	3.61 (4)
C5···O8	2.436 (2)	H2···H112	3.62 (2)
C2···O7	2.437 (2)	O10···O21	3.621 (2)
C2···O4	2.439 (2)	C22···H182	3.63 (2)
O7···H252	2.46 (2)	O24···H161	3.63 (2)
H111···H162	2.48 (3)	C1···C18	3.634 (3)
O4···H182	2.49 (2)	H113···H212	3.64 (4)
H2···H163	2.49 (3)	C14···H113	3.639 (18)
O10···H2	2.498 (14)	C1···C17	3.649 (3)
O21···H213	2.51 (2)	C9···C16	3.652 (3)
C12···H142	2.51 (4)	C19···H173	3.65 (2)
C19···H213	2.52 (2)	O4···C17	3.656 (2)
O10···H2	2.519 (17)	C14···H161	3.66 (2)
O8···H161	2.52 (3)	O13···H173	3.667 (17)
C18···H253	2.53 (3)	C18···H212	3.67 (4)
C3···C12	2.527 (3)	O13···H113	3.67 (2)
C1···C3	2.531 (3)	C16···H142	3.67 (4)
H112···H212	2.53 (4)	C2···H2	3.675 (15)
C6···H252	2.53 (3)	C5···H2	3.675 (15)
O8···H172	2.534 (19)	O15···H211	3.68 (3)
O8···H163	2.53 (2)	O10···O13	3.6800 (19)
C5···C18	2.539 (3)	C22···H173	3.68 (2)
O7···H161	2.54 (3)	C9···H212	3.68 (4)
O7···H162	2.54 (2)	C2···C14	3.683 (5)
O15···H142	2.54 (3)	O20···C25	3.683 (3)
C2···C11	2.547 (3)	C3···O21	3.687 (2)
O4···H111	2.548 (16)	C14···H213	3.69 (3)
O8···H171	2.55 (2)	C18···H253	3.70 (4)
C1···C12	2.552 (3)	O8···C11	3.700 (2)
O10···H112	2.555 (19)	C18···O21	3.701 (3)
C2···C16	2.557 (4)	C3···H181	3.70 (2)
O7···H182	2.56 (2)	C5···C25	3.705 (3)
C6···C9	2.571 (2)	C1···H141	3.71 (4)
O7···H111	2.58 (2)	C3···H182	3.71 (2)
O24···H183	2.59 (2)	O8···C25	3.715 (3)
H113···H163	2.59 (3)	O4···H181	3.717 (18)
C6···C19	2.589 (3)	C5···H112	3.719 (17)
C9···C19	2.596 (3)	C16···C22	3.719 (4)
C6···H253	2.60 (3)	C5···C22	3.722 (3)
C16···H2	2.602 (16)	C6···H111	3.72 (2)
O8···H2	2.603 (14)	C1···H182	3.73 (2)
H183···H253	2.61 (4)	C1···C25	3.729 (3)
O21···H181	2.607 (18)	C14···H2	3.732 (16)
H2···H113	2.61 (3)	O4···C25	3.733 (4)
O4···O21	2.615 (2)	O15···C16	3.735 (3)
O21···H173	2.62 (2)	O13···C17	3.737 (3)
C22···O21	2.617 (4)	O10···C12	3.738 (2)
O4···H112	2.617 (17)	O21···O21	3.738 (3)
O10···H173	2.626 (18)	C12···H113	3.74 (2)
C5···H182	2.63 (2)	C14···H162	3.74 (2)
C14···O15	2.629 (5)	O8···C19	3.744 (2)
C6···O8	2.634 (2)	C17···H113	3.75 (2)
O8···H141	2.64 (4)	C17···H251	3.75 (2)
O10···H172	2.637 (18)	C25···H143	3.75 (3)
C2···H162	2.64 (2)	C22···H171	3.75 (2)
O10···H113	2.651 (18)	C17···C18	3.754 (3)
C5···C17	2.653 (3)	O15···H113	3.76 (2)
C19···H212	2.66 (3)	O8···C12	3.763 (2)
C1···C5	2.677 (3)	C9···H112	3.764 (18)
H163···H211	2.68 (3)	C18···H251	3.77 (2)
O24···H181	2.685 (19)	C17···H182	3.77 (2)
H251···H251	2.69 (4)	C25···C25	3.771 (5)
C25···H181	2.69 (2)	C18···H111	3.77 (2)
O21···H212	2.70 (3)	C11···O13	3.777 (3)
H181···H252	2.72 (3)	C16···H112	3.787 (18)
C12···H141	2.72 (4)	C12···H172	3.789 (15)
O20···O24	2.721 (2)	C11···C12	3.790 (3)
O20···H171	2.72 (2)	C17···H143	3.79 (3)
O4···O7	2.7302 (19)	C17···O21	3.792 (3)
C2···H113	2.73 (2)	O7···C19	3.796 (2)
C2···C9	2.737 (2)	O4···H173	3.796 (18)
O24···H251	2.74 (2)	O8···H142	3.80 (4)
O8···H113	2.74 (2)	O8···H2	3.805 (14)
O15···H111	2.74 (2)	C17···H212	3.81 (4)
C12···H111	2.74 (2)	C11···H211	3.82 (3)
C12···H162	2.74 (2)	C22···H181	3.82 (2)
H2···H162	2.74 (3)	C17···H143	3.83 (3)
O13···H162	2.754 (18)	C3···H173	3.837 (18)
H112···H181	2.75 (3)	O8···H143	3.84 (3)
C3···O8	2.760 (2)	C25···H182	3.84 (2)
C11···H2	2.761 (17)	O13···H111	3.844 (16)
C19···H173	2.764 (18)	O20···H252	3.85 (2)
O15···H141	2.78 (4)	O24···O24	3.8458 (17)
C2···H163	2.79 (2)	C1···H181	3.847 (17)
C19···H183	2.80 (2)	C9···H163	3.85 (2)
C5···H183	2.80 (2)	C14···H253	3.85 (3)
O8···O24	2.7969 (16)	C1···H171	3.85 (2)
H141···H172	2.80 (4)	C12···H162	3.85 (2)
O20···H173	2.801 (18)	C22···H142	3.85 (3)
H112···H163	2.80 (3)	C18···H252	3.86 (2)
H173···H183	2.81 (3)	C6···H112	3.86 (2)
C2···H111	2.82 (2)	C17···H2	3.863 (14)
O7···C25	2.817 (3)	O20···H182	3.87 (2)
C1···O10	2.835 (2)	C12···H112	3.87 (2)
H163···H213	2.84 (3)	C3···C16	3.877 (4)
O10···H212	2.85 (4)	C2···H142	3.88 (4)
C5···H171	2.86 (2)	C5···H212	3.88 (4)
H171···H251	2.87 (3)	C6···O15	3.878 (2)
C1···O4	2.879 (2)	C18···H211	3.88 (3)
H161···H252	2.88 (3)	C18···H172	3.880 (17)
H113···H141	2.89 (4)	C17···H181	3.88 (2)
O7···C9	2.888 (2)	O21···H112	3.884 (17)
O7···C12	2.891 (2)	O7···O13	3.8843 (18)
C9···O24	2.896 (2)	C9···H161	3.89 (3)
O20···H251	2.90 (3)	O21···H182	3.89 (2)
O4···C18	2.903 (3)	C1···C11	3.892 (3)
C5···H173	2.905 (19)	C22···H183	3.89 (2)
H211···H251	2.91 (4)	C12···H182	3.89 (2)
H2···H113	2.91 (3)	C11···H172	3.899 (17)
O21···H253	2.91 (4)	C22···H252	3.90 (3)
O24···H171	2.93 (2)	O20···H182	3.90 (2)
H182···H252	2.93 (3)	C5···H181	3.91 (2)
H162···H213	2.94 (3)	O15···H161	3.91 (2)
C6···O20	2.953 (2)	C1···H172	3.908 (19)
O15···H112	2.954 (18)	C6···C12	3.909 (2)
C18···C25	2.955 (4)	O15···C18	3.909 (3)
H171···H183	2.96 (3)	C22···O21	3.909 (4)
H112···H211	2.97 (3)	O13···H113	3.915 (19)
H143···H253	2.97 (4)	C5···H111	3.915 (17)
H141···H171	2.97 (4)	C9···C18	3.920 (3)
C3···O15	2.979 (2)	C11···H182	3.92 (2)
C17···C19	2.982 (3)	C5···H252	3.92 (3)
H182···H253	2.98 (4)	C5···H253	3.93 (4)
C2···C5	2.983 (2)	C2···H182	3.93 (2)
C11···C12	2.989 (3)	C6···H162	3.93 (2)
O20···H183	2.99 (2)	C16···O24	3.932 (3)
O4···H181	2.99 (2)	O21···H172	3.934 (19)
C17···O20	2.997 (3)	C5···C12	3.936 (3)
C19···O24	2.997 (3)	C19···H172	3.939 (18)
C22···H163	3.02 (2)	O10···O10	3.9410 (19)
O4···O15	3.029 (2)	C19···O21	3.944 (3)
O13···H172	3.050 (16)	C14···C17	3.944 (7)
C18···C19	3.052 (3)	C11···C22	3.947 (5)
C12···H143	3.06 (3)	C16···H212	3.95 (3)
C9···H2	3.065 (15)	C3···H163	3.95 (2)
O7···O15	3.0686 (18)	C2···H111	3.95 (2)
C3···O7	3.072 (2)	O7···H113	3.95 (2)
H211···H252	3.07 (4)	C3···H172	3.956 (18)
O4···C12	3.076 (2)	O13···C22	3.958 (4)
C16···H111	3.08 (2)	C14···H163	3.96 (2)
C1···O24	3.078 (2)	C9···H113	3.958 (18)
O13···H213	3.08 (3)	O20···H172	3.961 (17)
C19···H171	3.08 (2)	C5···H213	3.96 (3)
O7···H112	3.08 (2)	O20···C25	3.970 (4)
H172···H183	3.09 (3)	O4···C18	3.971 (3)
O15···H2	3.087 (15)	O21···C25	3.974 (4)
H2···H2	3.11 (2)	O24···H173	3.97 (2)
C6···H251	3.11 (2)	C12···H161	3.98 (2)
H163···H212	3.11 (4)	C11···C18	3.980 (4)
C9···O20	3.115 (2)	O15···C16	3.982 (3)
C19···H211	3.12 (2)	O8···H112	3.992 (18)
O4···O8	3.1210 (17)	C19···H181	3.99 (2)
O21···H212	3.13 (3)	C17···H212	3.99 (3)
H113···H172	3.13 (3)	C2···H172	4.002 (15)
C18···H252	3.14 (3)	O8···H251	4.00 (2)
C11···H163	3.14 (2)	C6···H251	4.01 (2)
O8···H162	3.15 (2)	C3···O10	4.009 (2)
C17···H183	3.15 (2)	C5···H253	4.01 (3)
C12···C16	3.151 (3)	O4···O7	4.0100 (18)
H112···H182	3.15 (3)	C11···H252	4.02 (3)
O7···H253	3.15 (3)	C17···C22	4.028 (4)
C25···H251	3.16 (3)	C18···H143	4.03 (3)
C25···H183	3.16 (2)	C5···O15	4.032 (2)
C22···H112	3.16 (2)	C11···C16	4.034 (3)
O10···H171	3.17 (2)	C19···H251	4.04 (2)
H173···H212	3.17 (4)	C11···C16	4.037 (3)
H173···H181	3.17 (3)	C22···O24	4.042 (4)
O7···H2	3.176 (14)	O20···O21	4.062 (2)
H171···H253	3.18 (4)	C22···C25	4.072 (5)
H181···H212	3.18 (4)	C3···C18	4.082 (3)
C19···H182	3.18 (2)	O10···O20	4.0847 (18)
H2···H111	3.18 (3)	O8···O20	4.085 (2)
H111···H181	3.18 (3)	O10···C11	4.096 (3)
O7···H183	3.19 (2)	C18···C25	4.098 (4)
H142···H162	3.19 (4)	O8···C18	4.106 (2)
H111···H161	3.19 (3)	C9···C12	4.111 (3)
H182···H211	3.20 (3)	O10···C16	4.114 (3)
O4···H253	3.20 (4)	C16···C25	4.114 (4)
O4···H2	3.204 (16)	O10···C12	4.116 (2)
C12···H113	3.21 (2)	O21···O24	4.130 (2)
O4···H252	3.22 (3)	C18···C22	4.134 (5)
C17···H141	3.22 (4)	C5···C16	4.134 (3)
O24···H182	3.22 (2)	C1···C11	4.153 (3)
H143···H213	3.22 (4)	O7···C17	4.156 (3)
O10···C19	3.222 (2)	C2···C17	4.159 (3)
H141···H161	3.23 (5)	O8···C11	4.182 (3)
O4···H113	3.235 (18)	C9···C25	4.182 (3)
O10···H111	3.23 (2)	C2···C3	4.185 (2)
O8···H173	3.24 (2)	C2···C18	4.195 (3)
O7···H163	3.24 (2)	C14···C16	4.196 (5)
H143···H171	3.24 (4)	C1···C19	4.197 (3)
C25···H182	3.25 (2)	O10···O24	4.2014 (19)
C3···C6	3.252 (2)	C1···C11	4.213 (3)
O15···H161	3.25 (2)	C11···O13	4.213 (3)
C1···O15	3.253 (2)	C2···C11	4.218 (3)
H143···H172	3.26 (4)	O15···C16	4.223 (3)
O15···H182	3.259 (19)	C1···O10	4.228 (2)
C18···H173	3.271 (18)	C11···C14	4.239 (5)
C11···H212	3.27 (4)	C17···C25	4.251 (3)
C2···C6	3.274 (2)	C11···O21	4.258 (3)
C1···O13	3.288 (2)	C3···O7	4.265 (2)
H171···H182	3.30 (3)	C3···C22	4.268 (4)
O7···C11	3.298 (3)	O10···C16	4.271 (3)
C11···O15	3.298 (3)	C2···O24	4.274 (2)
C1···H111	3.31 (2)	C6···C11	4.276 (3)
H111···H252	3.31 (3)	C14···C17	4.286 (5)
C11···H181	3.316 (19)	C9···O13	4.288 (2)
H173···H212	3.32 (4)	O7···O20	4.289 (2)
O15···H111	3.325 (19)	O7···O15	4.299 (2)
C3···H2	3.326 (14)	C3···O24	4.309 (2)
C1···H252	3.33 (2)	O13···O21	4.311 (2)
H143···H183	3.33 (3)	C6···C22	4.331 (4)
C16···H213	3.34 (2)	O15···C25	4.335 (4)
C18···H112	3.34 (2)	O10···O15	4.3378 (18)
C25···H171	3.34 (2)	C14···O21	4.338 (5)
H182···H212	3.34 (4)	O4···O13	4.340 (2)
O13···C16	3.341 (3)	C18···O20	4.341 (3)
O4···H183	3.342 (18)	O8···O10	4.3454 (17)
O21···H173	3.34 (2)	O10···O21	4.348 (2)
C2···H112	3.34 (2)	C19···C25	4.358 (4)
C2···H161	3.35 (3)	C9···C14	4.358 (6)
O10···H113	3.35 (2)	O4···C16	4.361 (3)
O15···H113	3.35 (2)	C2···C2	4.367 (2)
C16···H113	3.35 (2)	C12···C18	4.368 (3)
C5···H181	3.359 (19)	C11···C19	4.373 (3)
H141···H163	3.36 (4)	C9···C11	4.376 (3)
H142···H161	3.36 (4)	C3···O8	4.377 (2)
C1···H113	3.37 (2)	C12···C16	4.379 (4)
H182···H251	3.37 (3)	C2···C9	4.381 (2)
C11···H162	3.37 (2)	C17···C22	4.390 (5)
H162···H211	3.38 (3)	C9···C22	4.412 (3)
O21···H183	3.38 (2)	C19···C22	4.425 (4)
C25···H211	3.39 (3)	C18···C19	4.426 (3)
C17···O24	3.401 (3)	C2···C19	4.429 (3)
O8—C1—O7	110.54 (12)	O15—C12—O13	122.96 (19)
O8—C1—C16	106.98 (16)	O15—C12—C2	127.11 (18)
O8—C1—C2	108.53 (14)	O13—C12—C2	109.91 (16)
O7—C1—C16	107.39 (16)	C12—O13—C14	115.6 (2)
O7—C1—C2	109.93 (14)	H141—C14—H142	119 (3)
C16—C1—C2	113.44 (15)	H141—C14—H143	107 (3)
H2—C2—C12	107.6 (9)	H141—C14—O13	115 (2)
H2—C2—C3	108.2 (11)	H142—C14—H143	111 (3)
H2—C2—C1	104.7 (9)	H142—C14—O13	104 (2)
C12—C2—C3	112.45 (16)	H143—C14—O13	98 (2)
C12—C2—C1	113.31 (16)	H161—C16—H162	117.4 (19)
C3—C2—C1	110.17 (14)	H161—C16—H163	105.0 (18)
O10—C3—O4	103.25 (12)	H161—C16—C1	109.5 (16)
O10—C3—C11	110.33 (15)	H162—C16—H163	110.4 (16)
O10—C3—C2	107.14 (14)	H162—C16—C1	104.9 (13)
O4—C3—C11	110.13 (15)	H163—C16—C1	109.7 (13)
O4—C3—C2	110.78 (14)	H171—C17—H172	106.8 (17)
C11—C3—C2	114.56 (15)	H171—C17—H173	108.2 (17)
C5—O4—C3	106.76 (12)	H171—C17—C9	109.3 (14)
O4—C5—C19	105.98 (14)	H172—C17—H173	108.7 (15)
O4—C5—C6	107.29 (13)	H172—C17—C9	111.0 (10)
O4—C5—C9	103.73 (11)	H173—C17—C9	112.6 (11)
C19—C5—C6	114.34 (13)	H182—C18—H183	110.5 (18)
C19—C5—C9	113.52 (14)	H182—C18—H181	111.5 (17)
C6—C5—C9	111.08 (14)	H182—C18—C6	107.7 (12)
O24—C6—O7	110.62 (14)	H183—C18—H181	111.7 (15)
O24—C6—C18	113.32 (14)	H183—C18—C6	109.0 (13)
O24—C6—C5	106.20 (14)	H181—C18—C6	106.1 (11)
O7—C6—C18	106.12 (15)	O21—C19—O20	123.27 (18)
O7—C6—C5	108.17 (12)	O21—C19—C5	123.86 (16)
C18—C6—C5	112.36 (17)	O20—C19—C5	112.85 (16)
C6—O7—C1	116.94 (13)	C19—O20—C22	116.0 (2)
C9—O8—C1	112.50 (13)	H212—C22—H213	111 (3)
O10—C9—O8	108.74 (12)	H212—C22—H211	107 (3)
O10—C9—C17	109.69 (15)	H212—C22—O20	114 (2)
O10—C9—C5	101.47 (13)	H213—C22—H211	115 (2)
O8—C9—C17	107.67 (16)	H213—C22—O20	105.9 (16)
O8—C9—C5	109.13 (14)	H211—C22—O20	103.9 (16)
C17—C9—C5	119.68 (14)	C6—O24—C25	115.23 (18)
C9—O10—C3	103.23 (12)	H251—C25—H252	111 (2)
H112—C11—H113	105.3 (17)	H251—C25—H253	122 (2)
H112—C11—H111	106.4 (17)	H251—C25—O24	106.0 (17)
H112—C11—C3	111.8 (11)	H252—C25—H253	102 (2)
H113—C11—H111	114.7 (15)	H252—C25—O24	109.8 (15)
H113—C11—C3	110.6 (12)	H253—C25—O24	104.4 (18)
H111—C11—C3	108.0 (10)
O7—C1—C2—C3	74.73 (17)	C9—C5—C6—O24	61.99 (16)
O7—C1—C2—C12	−52.2 (2)	C19—C5—C6—O7	173.15 (13)
O7—C1—C2—H2	−169.2 (11)	C19—C5—C6—C18	56.3 (2)
O8—C1—C2—C3	−46.27 (18)	C19—C5—C6—O24	−68.08 (17)
O8—C1—C2—C12	−173.23 (14)	O4—C5—C9—O8	−96.08 (14)
O8—C1—C2—H2	69.8 (11)	O4—C5—C9—O10	18.59 (16)
C16—C1—C2—C3	−165.03 (16)	O4—C5—C9—C17	139.34 (17)
C16—C1—C2—C12	68.0 (2)	C6—C5—C9—O8	18.88 (16)
C16—C1—C2—H2	−48.9 (11)	C6—C5—C9—O10	133.55 (13)
C2—C1—O7—C6	−93.74 (16)	C6—C5—C9—C17	−105.7 (2)
O8—C1—O7—C6	26.0 (2)	C19—C5—C9—O8	149.38 (13)
C16—C1—O7—C6	142.41 (15)	C19—C5—C9—O10	−95.95 (15)
C2—C1—O8—C9	51.10 (16)	C19—C5—C9—C17	24.8 (2)
O7—C1—O8—C9	−69.53 (16)	O4—C5—C19—O20	173.27 (14)
C16—C1—O8—C9	173.86 (13)	O4—C5—C19—O21	−8.4 (2)
C2—C1—C16—H161	178.4 (15)	C6—C5—C19—O20	55.3 (2)
C2—C1—C16—H162	−54.8 (11)	C6—C5—C19—O21	−126.4 (2)
C2—C1—C16—H163	63.8 (12)	C9—C5—C19—O20	−73.54 (19)
O7—C1—C16—H161	−59.9 (15)	C9—C5—C19—O21	104.8 (2)
O7—C1—C16—H162	66.8 (11)	C5—C6—O7—C1	33.52 (18)
O7—C1—C16—H163	−174.6 (12)	C18—C6—O7—C1	154.29 (15)
O8—C1—C16—H161	58.8 (15)	O24—C6—O7—C1	−82.41 (17)
O8—C1—C16—H162	−174.5 (11)	C5—C6—C18—H181	169.7 (10)
O8—C1—C16—H163	−55.9 (12)	C5—C6—C18—H182	50.1 (15)
C1—C2—C3—O4	−54.65 (17)	C5—C6—C18—H183	−69.8 (13)
C1—C2—C3—O10	57.29 (16)	O7—C6—C18—H181	51.7 (10)
C1—C2—C3—C11	−179.98 (15)	O7—C6—C18—H182	−67.9 (15)
C12—C2—C3—O4	72.79 (16)	O7—C6—C18—H183	172.2 (13)
C12—C2—C3—O10	−175.27 (12)	O24—C6—C18—H181	−69.9 (10)
C12—C2—C3—C11	−52.5 (2)	O24—C6—C18—H182	170.5 (15)
H2—C2—C3—O4	−168.5 (9)	O24—C6—C18—H183	50.6 (13)
H2—C2—C3—O10	−56.6 (9)	C5—C6—O24—C25	−174.5 (2)
H2—C2—C3—C11	66.2 (9)	O7—C6—O24—C25	−57.4 (2)
C1—C2—C12—O13	−99.72 (18)	C18—C6—O24—C25	61.7 (3)
C1—C2—C12—O15	81.6 (3)	C1—O8—C9—C5	42.11 (15)
C3—C2—C12—O13	134.53 (16)	C1—O8—C9—O10	−67.76 (15)
C3—C2—C12—O15	−44.1 (3)	C1—O8—C9—C17	173.45 (13)
H2—C2—C12—O13	15.5 (11)	C5—C9—O10—C3	−39.80 (16)
H2—C2—C12—O15	−163.2 (11)	O8—C9—O10—C3	75.16 (15)
C2—C3—O4—C5	79.63 (15)	C17—C9—O10—C3	−167.33 (16)
O10—C3—O4—C5	−34.78 (16)	C5—C9—C17—H171	62.1 (15)
C11—C3—O4—C5	−152.58 (15)	C5—C9—C17—H172	179.7 (11)
C2—C3—O10—C9	−69.42 (15)	C5—C9—C17—H173	−58.2 (11)
O4—C3—O10—C9	47.59 (16)	O8—C9—C17—H171	−63.1 (15)
C11—C3—O10—C9	165.25 (15)	O8—C9—C17—H172	54.4 (11)
C2—C3—C11—H111	70.7 (11)	O8—C9—C17—H173	176.6 (11)
C2—C3—C11—H112	−172.6 (13)	O10—C9—C17—H171	178.7 (15)
C2—C3—C11—H113	−55.6 (14)	O10—C9—C17—H172	−63.8 (11)
O4—C3—C11—H111	−55.0 (11)	O10—C9—C17—H173	58.4 (11)
O4—C3—C11—H112	61.8 (13)	C2—C12—O13—C14	−178.0 (3)
O4—C3—C11—H113	178.7 (14)	O15—C12—O13—C14	0.8 (4)
O10—C3—C11—H111	−168.3 (11)	C12—O13—C14—H141	−73 (3)
O10—C3—C11—H112	−51.6 (13)	C12—O13—C14—H142	60 (2)
O10—C3—C11—H113	65.4 (14)	C12—O13—C14—H143	175 (2)
C3—O4—C5—C6	−107.96 (14)	C5—C19—O20—C22	177.3 (2)
C3—O4—C5—C9	9.68 (17)	O21—C19—O20—C22	−1.0 (3)
C3—O4—C5—C19	129.49 (14)	C19—O20—C22—H211	178.5 (16)
O4—C5—C6—O7	55.95 (16)	C19—O20—C22—H212	−65 (2)
O4—C5—C6—C18	−60.86 (17)	C19—O20—C22—H213	57.0 (15)
O4—C5—C6—O24	174.72 (12)	C6—O24—C25—H251	169.7 (17)
C9—C5—C6—O7	−56.78 (16)	C6—O24—C25—H252	49.3 (18)
C9—C5—C6—C18	−173.59 (14)	C6—O24—C25—H253	−60.0 (17)

(5ax)

Crystal data

C13H20O7	F(000) = 616
Mr = 288.3	Dx = 1.36 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 11.498 (3) Å	θ = 14.8–21.2°
b = 8.4175 (8) Å	µ = 0.11 mm^−1
c = 15.632 (4) Å	T = 293 K
β = 111.47 (1)°	Irregular, colourless
V = 1408.0 (5) Å^3	0.50 × 0.50 × 0.40 mm
Z = 4

Data collection

CAD4 diffractometer	Rint = 0.03
Radiation source: Cu anode	θmax = 27.4°, θmin = 1.9°
Graphite monochromator	h = −14→13
ω/2θ scans	k = −7→10
4175 measured reflections	l = 0→20
3196 independent reflections	3 standard reflections every 400 reflections
3196 reflections with F^2 > .00 sig(F^2)	intensity decay: 1%

Refinement

Refinement on F^2	0 constraints
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.063	w = 1/[(7.15σ^2(F^2)]
wR(F^2) = 0.064	(Δ/σ)max = 0.007
S = 1.00	Δρmax = 0.33 e Å^−3
3196 reflections	Δρmin = −0.25 e Å^−3
262 parameters	Extinction correction: Zachariasen, Eq22 p292 "Cryst. Comp." Munksgaard 1970
0 restraints	Extinction coefficient: 2211 (120)

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

	x	y	z	Uiso*/Ueq
C1	0.75057 (14)	0.48645 (19)	0.52768 (10)	0.0339 (7)
C2	0.66132 (14)	0.63060 (18)	0.49095 (10)	0.0302 (7)
C3	0.58435 (14)	0.61156 (18)	0.38780 (11)	0.0321 (7)
O4	0.66201 (10)	0.58960 (12)	0.33649 (7)	0.0351 (5)
C5	0.70268 (14)	0.42482 (18)	0.34992 (11)	0.0339 (7)
C6	0.83948 (15)	0.4233 (2)	0.41315 (12)	0.0403 (8)
O7	0.85421 (9)	0.49483 (13)	0.50026 (7)	0.0409 (6)
O8	0.68135 (10)	0.34491 (12)	0.49378 (7)	0.0345 (5)
C9	0.61653 (14)	0.35120 (18)	0.39690 (11)	0.0323 (7)
O10	0.51881 (9)	0.46433 (12)	0.37753 (7)	0.0355 (5)
C11	0.49233 (18)	0.7443 (2)	0.34676 (15)	0.0464 (9)
C12	0.73104 (14)	0.7867 (2)	0.51287 (11)	0.0338 (7)
O13	0.74202 (12)	0.83846 (14)	0.59621 (8)	0.0522 (7)
C14	0.8075 (3)	0.9888 (3)	0.62356 (17)	0.0681 (14)
O15	0.77094 (12)	0.85830 (14)	0.46402 (8)	0.0496 (7)
C16	0.8009 (2)	0.4749 (3)	0.63127 (13)	0.0538 (11)
C17	0.56180 (18)	0.1889 (2)	0.36743 (14)	0.0416 (9)
C18	0.8993 (2)	0.2588 (3)	0.42789 (19)	0.0565 (11)
C19	0.6800 (2)	0.3544 (2)	0.25581 (13)	0.0467 (10)
O20	0.75870 (15)	0.43166 (16)	0.21817 (10)	0.0738 (9)
H14a	0.8108 (18)	1.009 (3)	0.6841 (14)	0.085 (7)*
H14b	0.7609 (18)	1.081 (2)	0.5776 (13)	0.085 (7)*
H14c	0.888 (2)	0.981 (3)	0.6216 (17)	0.121 (12)*
H18a	0.982 (2)	0.269 (2)	0.4704 (13)	0.083 (7)*
H18b	0.9076 (17)	0.223 (2)	0.3686 (13)	0.073 (7)*
H18c	0.8475 (17)	0.183 (2)	0.4493 (12)	0.074 (7)*
H17a	0.5088 (17)	0.192 (2)	0.3015 (12)	0.070 (6)*
H17b	0.5135 (16)	0.162 (2)	0.4013 (11)	0.055 (6)*
H17c	0.6274 (17)	0.109 (2)	0.3800 (11)	0.063 (6)*
H16a	0.7346 (17)	0.477 (2)	0.6572 (12)	0.071 (7)*
H16b	0.8658 (16)	0.560 (2)	0.6590 (11)	0.060 (6)*
H16c	0.8454 (16)	0.378 (2)	0.6499 (12)	0.062 (6)*
H11a	0.5373 (18)	0.847 (2)	0.3466 (13)	0.082 (7)*
H11b	0.4384 (17)	0.757 (2)	0.3809 (13)	0.077 (7)*
H11c	0.4402 (17)	0.715 (2)	0.2831 (13)	0.074 (7)*
H19a	0.7009 (14)	0.2406 (19)	0.2634 (10)	0.042 (5)*
H19b	0.5869 (11)	0.3721 (14)	0.2032 (8)	0.013 (3)*
H2a	0.6042 (12)	0.6255 (15)	0.5225 (8)	0.023 (4)*
H6a	0.8860 (13)	0.4965 (18)	0.3852 (9)	0.039 (4)*
H20	0.731 (4)	0.364 (4)	0.142 (3)	0.28 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0402 (9)	0.0253 (8)	0.0336 (9)	−0.0041 (7)	0.0103 (7)	−0.0003 (7)
C2	0.0361 (8)	0.0265 (8)	0.0320 (8)	−0.0025 (7)	0.0171 (7)	−0.0026 (7)
C3	0.0348 (8)	0.0253 (8)	0.0360 (9)	−0.0007 (7)	0.0125 (7)	−0.0017 (7)
O4	0.0496 (7)	0.0256 (6)	0.0342 (6)	0.0024 (5)	0.0202 (5)	0.0010 (5)
C5	0.0431 (9)	0.0227 (8)	0.0397 (9)	−0.0003 (7)	0.0195 (8)	−0.0021 (7)
C6	0.0389 (9)	0.0321 (9)	0.0556 (11)	−0.0007 (7)	0.0239 (9)	−0.0017 (9)
O7	0.0329 (6)	0.0364 (7)	0.0500 (7)	−0.0014 (5)	0.0109 (5)	−0.0040 (6)
O8	0.0433 (6)	0.0256 (6)	0.0330 (6)	−0.0043 (5)	0.0121 (5)	0.0019 (5)
C9	0.0336 (8)	0.0266 (8)	0.0364 (9)	−0.0014 (7)	0.0124 (7)	−0.0022 (7)
O10	0.0332 (6)	0.0258 (6)	0.0450 (7)	−0.0014 (5)	0.0111 (5)	−0.0049 (5)
C11	0.0459 (11)	0.0325 (10)	0.0515 (12)	0.0076 (9)	0.0069 (10)	−0.0005 (9)
C12	0.0377 (8)	0.0294 (9)	0.0330 (9)	0.0012 (7)	0.0115 (7)	−0.0010 (7)
O13	0.0851 (10)	0.0331 (7)	0.0403 (7)	−0.0149 (7)	0.0251 (7)	−0.0107 (6)
C14	0.107 (2)	0.0340 (12)	0.0489 (14)	−0.0197 (13)	0.0118 (14)	−0.0131 (11)
O15	0.0703 (8)	0.0379 (7)	0.0469 (7)	−0.0170 (6)	0.0290 (7)	−0.0038 (6)
C16	0.0718 (14)	0.0416 (12)	0.0357 (11)	−0.0028 (11)	0.0053 (10)	0.0029 (9)
C17	0.0460 (10)	0.0276 (9)	0.0518 (12)	−0.0074 (8)	0.0187 (10)	−0.0053 (9)
C18	0.0432 (11)	0.0402 (12)	0.0860 (17)	0.0070 (10)	0.0235 (12)	−0.0048 (12)
C19	0.0708 (13)	0.0323 (10)	0.0466 (11)	0.0001 (9)	0.0331 (11)	−0.0051 (9)
O20	0.1242 (13)	0.0508 (9)	0.0733 (10)	−0.0132 (9)	0.0682 (10)	−0.0092 (8)

Geometric parameters (Å, º)

C1—O7	1.408 (2)	C11—H11c	0.986 (17)
C1—O8	1.4231 (18)	C11—H11a	1.01 (2)
C1—C16	1.510 (2)	C12—O15	1.189 (2)
C1—C2	1.557 (2)	C12—O13	1.335 (2)
C2—H2a	0.956 (16)	O13—C14	1.455 (3)
C2—C12	1.512 (2)	C14—H14c	0.93 (3)
C2—C3	1.538 (2)	C14—H14a	0.95 (2)
C3—O4	1.414 (2)	C14—H14b	1.062 (19)
C3—O10	1.4287 (18)	C16—H16c	0.948 (18)
C3—C11	1.511 (2)	C16—H16a	0.99 (2)
O4—C5	1.4542 (18)	C16—H16b	1.010 (17)
C5—C19	1.517 (3)	C17—H17b	0.92 (2)
C5—C6	1.521 (2)	C17—H17c	0.977 (18)
C5—C9	1.561 (3)	C17—H17a	0.987 (17)
C6—H6a	1.014 (17)	C18—H18a	0.941 (18)
C6—O7	1.441 (2)	C18—H18c	1.01 (2)
C6—C18	1.526 (3)	C18—H18b	1.01 (2)
O8—C9	1.4232 (18)	C19—H19a	0.985 (16)
C9—O10	1.4185 (18)	C19—H19b	1.096 (11)
C9—C17	1.504 (2)	C19—O20	1.406 (3)
C11—H11b	0.96 (2)	O20—H20	1.25 (4)
H17b···H17c	1.53 (3)	O7···O7	3.3566 (18)
H16b···H16c	1.55 (3)	O7···C18	3.357 (2)
H18a···H18b	1.55 (2)	C2···H16c	3.364 (16)
H14a···H14c	1.56 (4)	C17···H14b	3.369 (17)
H16a···H16c	1.56 (3)	C17···H2a	3.383 (15)
H17a···H17b	1.56 (3)	C11···H14a	3.387 (19)
H11b···H11c	1.58 (3)	C2···H11c	3.388 (16)
H14b···H14c	1.61 (3)	H18b···H20	3.39 (4)
H11a···H11b	1.61 (3)	C6···H18a	3.39 (2)
H17a···H17c	1.62 (2)	C11···H17c	3.391 (18)
H18a···H18c	1.63 (3)	C5···H17b	3.40 (2)
H11a···H11c	1.63 (3)	C9···H6a	3.398 (16)
H16a···H16b	1.65 (3)	C18···O20	3.406 (3)
O15···H20	1.65 (5)	C16···H14b	3.41 (2)
H14a···H14b	1.67 (3)	C2···H20	3.41 (5)
H18b···H18c	1.68 (3)	C5···H20	3.42 (5)
H19a···H19b	1.711 (18)	H18b···H11c	3.42 (3)
O13···H14a	1.94 (2)	H18b···H17c	3.43 (3)
O7···H6a	1.962 (17)	H14c···H16c	3.43 (3)
O20···H19b	1.967 (13)	C3···C19	3.437 (3)
O20···H19a	1.968 (17)	C12···H16a	3.44 (2)
O13···H14c	1.98 (3)	H18a···H16b	3.44 (3)
C9···H17b	2.000 (18)	H17c···H19b	3.44 (2)
C6···H18a	2.02 (2)	H14a···H17a	3.44 (3)
C1···H2a	2.027 (14)	H17a···H16a	3.44 (2)
C1···H16c	2.036 (16)	C17···H16c	3.446 (15)
C3···H2a	2.036 (14)	H16c···H2a	3.46 (2)
C12···H2a	2.038 (14)	H19a···H20	3.46 (4)
C3···H11b	2.05 (2)	C18···H14c	3.47 (3)
C9···H17a	2.049 (17)	H16c···H6a	3.49 (3)
C3···H11c	2.050 (16)	C1···H14b	3.49 (2)
C5···H19a	2.053 (16)	C16···H11c	3.496 (18)
C19···H20	2.06 (5)	O4···C19	3.503 (3)
C5···H6a	2.064 (15)	C2···O10	3.503 (2)
C9···H17c	2.068 (18)	H17b···H11b	3.50 (3)
C6···H18b	2.08 (2)	C6···H17c	3.508 (18)
O13···H14b	2.09 (2)	H19b···H6a	3.51 (2)
C1···H16b	2.089 (15)	C2···H17b	3.52 (2)
C3···H11a	2.09 (2)	C6···H19b	3.523 (10)
C6···H18c	2.09 (2)	C14···H11b	3.53 (2)
C18···H6a	2.097 (15)	C3···H19b	3.528 (13)
C1···H16a	2.10 (2)	C9···H14b	3.530 (19)
H19b···H20	2.19 (5)	C19···H14c	3.53 (2)
O13···O15	2.216 (2)	O15···H14a	3.53 (2)
C3···C9	2.218 (2)	C6···O10	3.539 (2)
C5···H19b	2.234 (11)	H18c···H16c	3.55 (3)
O4···O10	2.2378 (17)	C3···H16a	3.55 (2)
C3···C5	2.294 (2)	O20···H17a	3.56 (2)
H19a···H20	2.29 (5)	O15···H19b	3.557 (15)
O8···O10	2.3063 (13)	C12···H17b	3.56 (2)
O7···O8	2.3251 (16)	H14b···H19b	3.56 (2)
C5···O10	2.331 (2)	C17···O20	3.572 (3)
H18b···H6a	2.34 (2)	C3···C17	3.573 (2)
H18b···H19a	2.35 (2)	H16a···H11c	3.57 (2)
C2···O13	2.3478 (18)	C16···H14a	3.57 (2)
O7···C16	2.349 (3)	C9···C11	3.575 (2)
O8···C17	2.351 (2)	H18b···H20	3.58 (4)
O8···C16	2.355 (2)	C19···H19a	3.582 (16)
C1···C9	2.355 (2)	H6a···H6a	3.587 (17)
C12···C14	2.355 (3)	C5···H19a	3.587 (17)
O4···C9	2.357 (2)	C3···H2a	3.588 (15)
H18a···H6a	2.36 (2)	H18a···H19b^i	3.59 (2)
C5···O20	2.373 (3)	C6···C17	3.595 (3)
C2···O10	2.3792 (17)	C1···H18a	3.60 (2)
O10···C17	2.388 (2)	H11c···H2a	3.60 (2)
O13···H2a	2.391 (12)	C18···H14b	3.60 (2)
O4···C19	2.397 (2)	O8···H6a	3.601 (17)
O4···C11	2.399 (3)	H16b···H11b	3.60 (3)
O4···C6	2.4020 (19)	C19···H18b	3.605 (19)
O10···C11	2.402 (2)	C5···C11	3.605 (3)
H17c···H11a	2.41 (3)	C11···H17b	3.606 (17)
C2···O15	2.414 (2)	H14b···H16a	3.61 (3)
C2···O8	2.4147 (18)	O8···C14	3.612 (3)
C1···C6	2.424 (3)	H14c···H16b	3.61 (3)
C5···O7	2.4306 (17)	C18···O20	3.614 (3)
O7···C18	2.434 (3)	C6···H6a	3.615 (12)
H16a···H2a	2.44 (2)	C3···H6a	3.616 (16)
H18c···H17c	2.44 (3)	C19···O20	3.621 (2)
C2···O4	2.442 (2)	C6···C16	3.622 (3)
C5···O8	2.444 (2)	H17b···H19a	3.62 (3)
C2···O7	2.452 (2)	O15···C17	3.626 (2)
O8···H17b	2.477 (16)	O7···O10	3.6336 (16)
O8···H16c	2.495 (15)	C14···H16a	3.63 (2)
O7···H16b	2.497 (18)	C3···O13	3.637 (2)
H17a···H16c	2.50 (2)	H18c···H17b	3.64 (3)
H14c···H19b	2.51 (3)	O7···H18b	3.637 (17)
O10···H2a	2.512 (12)	C1···H11b	3.64 (2)
H17a···H19a	2.52 (3)	C18···H20	3.64 (4)
O4···H6a	2.528 (15)	C1···C17	3.644 (2)
H17c···H19a	2.53 (3)	C19···H6a	3.645 (15)
C3···C12	2.535 (2)	C9···C16	3.649 (2)
C6···C19	2.539 (2)	O4···C17	3.653 (2)
C1···C12	2.541 (2)	O8···H18a	3.66 (2)
O20···H6a	2.542 (13)	O15···H11b	3.660 (19)
O7···H18a	2.54 (2)	O10···C16	3.664 (3)
H17a···H19b	2.54 (3)	C17···H20	3.67 (4)
H14a···H11c	2.55 (3)	O15···C18	3.676 (3)
O10···H11c	2.545 (19)	C14···H16b	3.677 (18)
C1···C3	2.546 (2)	C2···H2a	3.680 (14)
O15···H14c	2.55 (2)	O15···C19	3.680 (3)
C6···C9	2.555 (3)	C18···H6a	3.687 (13)
C2···C16	2.555 (2)	C17···C18	3.689 (3)
C5···C18	2.556 (3)	C1···H18a	3.69 (2)
C12···H14c	2.56 (2)	C14···H18b	3.69 (2)
C2···C11	2.562 (2)	C9···H18b	3.69 (2)
C9···C19	2.564 (3)	C5···H2a	3.694 (15)
O10···H17a	2.565 (19)	C6···H16c	3.70 (2)
O8···H14b	2.57 (2)	C2···C14	3.697 (3)
O7···H16c	2.57 (2)	O7···O13	3.7009 (18)
O10···H17b	2.575 (17)	C3···H14a	3.705 (17)
O10···H2a	2.575 (16)	O15···H6a	3.707 (16)
H11b···H2a	2.58 (2)	C16···H6a	3.709 (17)
O4···H20	2.58 (4)	O8···C19	3.715 (3)
O8···H17c	2.588 (17)	C2···H6a	3.716 (17)
O4···H11c	2.600 (18)	O4···H14c	3.72 (2)
C16···H2a	2.608 (12)	C11···O20	3.720 (3)
H11a···H20	2.61 (5)	O10···H19a	3.722 (18)
C14···O15	2.615 (3)	C5···H11c	3.724 (19)
O15···H14b	2.61 (2)	O4···H17a	3.728 (19)
O8···H2a	2.619 (13)	O15···H18b	3.728 (16)
H16b···H11c	2.62 (3)	O7···H20	3.74 (4)
O4···H11a	2.63 (2)	O10···C12	3.7438 (18)
O20···H19a	2.638 (16)	C9···H11c	3.745 (18)
O10···H11b	2.64 (2)	C6···H19a	3.745 (16)
O8···H18c	2.64 (2)	C14···H17c	3.746 (16)
C5···C17	2.639 (3)	O13···C17	3.746 (3)
O15···H11a	2.643 (17)	O13···H11a	3.748 (17)
O8···H16a	2.645 (19)	O10···H14c	3.75 (2)
C6···O8	2.647 (2)	O8···C12	3.758 (2)
C12···H14b	2.65 (2)	O15···H17b	3.760 (17)
O7···H18a	2.66 (2)	C18···H16b	3.76 (2)
O4···H19b	2.668 (12)	C3···H17a	3.767 (18)
C1···C5	2.678 (2)	C5···H20	3.77 (4)
H14b···H18c	2.69 (3)	C16···H11a	3.777 (17)
C12···H20	2.70 (5)	C9···O20	3.779 (3)
C19···H17a	2.70 (2)	O13···H17a	3.78 (2)
C17···H19a	2.701 (18)	C11···H14c	3.78 (2)
O15···H17c	2.703 (17)	C14···H17b	3.787 (19)
H16a···H11b	2.71 (3)	O15···H16b	3.789 (17)
C2···C9	2.721 (2)	O8···H19a	3.792 (17)
H17c···H20	2.73 (5)	O4···C18	3.793 (2)
C2···H11b	2.726 (17)	O7···C19	3.796 (2)
C5···H18c	2.727 (18)	O8···C11	3.796 (3)
H14a···H16a	2.73 (3)	O13···H18a	3.80 (2)
O13···H16b	2.732 (17)	O15···C18	3.804 (3)
O7···H18c	2.74 (2)	C11···H14b	3.81 (2)
C2···H16a	2.745 (18)	C11···C17	3.816 (3)
C18···H19a	2.746 (13)	O15···H19a	3.817 (17)
C11···H2a	2.759 (12)	C14···H2a	3.823 (13)
C19···H6a	2.761 (13)	C19···H17b	3.83 (2)
H17b···H2a	2.76 (2)	C6···H20	3.83 (4)
C9···H19a	2.765 (18)	C17···H16b	3.835 (16)
C6···H19a	2.766 (14)	C16···H11c	3.84 (2)
C3···O8	2.7701 (18)	O10···C14	3.842 (3)
H14b···H16c	2.77 (3)	C6···C12	3.843 (3)
C12···H11a	2.782 (16)	C11···H17a	3.852 (19)
O20···H17c	2.79 (2)	C1···H17b	3.852 (16)
C19···H18b	2.792 (17)	C12···O20	3.855 (3)
O10···H16a	2.81 (2)	C12···H18c	3.86 (2)
O15···O20	2.810 (2)	O13···H20	3.86 (5)
O4···O20	2.816 (2)	C9···H11b	3.86 (2)
O4···O7	2.8163 (14)	C18···H14c	3.87 (3)
H18c···H19a	2.82 (2)	C9···H16c	3.874 (15)
H17b···H11a	2.83 (3)	C18···H16c	3.88 (2)
C5···H18b	2.83 (2)	C1···H17c	3.880 (17)
C1···O10	2.8401 (16)	C18···H19b	3.880 (13)
C6···O20	2.843 (3)	C12···H18b	3.882 (18)
C2···H11a	2.844 (18)	C3···C16	3.882 (2)
C9···H18c	2.85 (2)	O13···H17c	3.882 (17)
C5···H17a	2.854 (18)	C11···C14	3.887 (3)
O15···H18a	2.86 (2)	C6···O15	3.889 (2)
O7···H6a	2.867 (13)	C3···H17b	3.892 (17)
H14c···H18b	2.87 (3)	C1···H6a	3.895 (15)
C2···H16b	2.874 (15)	O13···H18b	3.90 (2)
O7···C12	2.878 (2)	O4···H20	3.90 (5)
O7···C9	2.8824 (18)	C5···C12	3.907 (2)
O4···H19a	2.888 (18)	C19···H18a	3.908 (17)
H14c···H11c	2.89 (3)	O8···O10	3.9129 (18)
C5···H17c	2.890 (18)	C1···O10	3.914 (2)
C17···H11a	2.90 (2)	C6···C6	3.915 (2)
O15···H18c	2.91 (2)	C6···H16b	3.916 (18)
O8···H11b	2.91 (2)	O20···H11c	3.92 (2)
C3···O15	2.9095 (19)	C14···H18a	3.92 (2)
H14b···H17c	2.91 (2)	O8···H18b	3.92 (2)
H18c···H6a	2.91 (3)	C1···C11	3.921 (2)
C1···O4	2.915 (2)	O13···H11b	3.922 (16)
C9···H19b	2.925 (13)	C3···O20	3.931 (2)
C17···C19	2.927 (3)	C11···H14a	3.93 (2)
O20···H18b	2.931 (17)	C9···H16a	3.935 (18)
H14b···H11b	2.93 (3)	C17···H11b	3.94 (2)
C12···H16b	2.945 (16)	C11···H18b	3.94 (2)
C14···H11c	2.952 (18)	O13···H16a	3.94 (2)
O13···H17b	2.95 (2)	C16···H18c	3.94 (2)
O20···H11a	2.96 (2)	O8···H14c	3.94 (2)
H18a···H6a	2.96 (2)	C9···H11b	3.94 (2)
O4···O15	2.9716 (15)	C6···H16b	3.95 (2)
C2···C5	2.976 (3)	C14···H17a	3.950 (17)
H16b···H11a	2.98 (2)	O4···H14a	3.953 (18)
H17a···H11a	2.98 (3)	C12···H11c	3.956 (16)
H16a···H11c	2.98 (3)	O7···H14b	3.96 (2)
H19a···H6a	2.99 (2)	C17···H11b	3.96 (2)
O13···H11c	3.010 (16)	O4···H19b	3.961 (14)
H18c···H20	3.02 (4)	C12···H6a	3.966 (17)
C11···C12	3.031 (2)	C2···H14c	3.97 (2)
H16b···H2a	3.035 (19)	C11···C16	3.967 (4)
C18···C19	3.045 (3)	O20···H18c	3.972 (19)
C19···H17c	3.05 (2)	C1···H2a	3.975 (14)
C17···H18c	3.058 (19)	O8···H14a	3.98 (2)
O4···C12	3.063 (2)	C17···H18b	3.98 (2)
C9···H2a	3.067 (14)	O15···H18b	3.98 (2)
H14c···H18c	3.08 (3)	C11···O13	3.982 (2)
H2a···H2a	3.076 (18)	C6···H20	3.98 (4)
H17a···H16b	3.08 (2)	C11···O13	3.985 (2)
C17···H19b	3.097 (14)	C9···H18a	3.99 (2)
O20···H18b	3.101 (18)	C16···H14a	4.00 (2)
O10···H14a	3.102 (17)	O15···H11c	4.005 (16)
O15···H2a	3.104 (15)	C12···H16c	4.009 (18)
C3···O7	3.1129 (18)	C5···O15	4.011 (2)
C12···H14a	3.11 (2)	C12···H17b	4.011 (16)
O8···C18	3.123 (3)	C2···H18a	4.01 (2)
H19a···H6a	3.14 (2)	C3···H14c	4.02 (2)
O13···C16	3.139 (2)	C5···H11a	4.02 (2)
C12···C16	3.142 (3)	C12···C18	4.024 (3)
C1···H6a	3.152 (17)	C12···H11c	4.024 (17)
O4···O8	3.1522 (16)	C9···H14a	4.032 (17)
C3···H20	3.16 (4)	C11···H16c	4.04 (2)
C1···O13	3.164 (2)	C2···O8	4.039 (2)
H18b···H19b	3.17 (2)	C16···H18a	4.04 (2)
H11a···H2a	3.18 (2)	C11···C16	4.044 (3)
C16···H17a^i	3.180 (16)	O10···O10	4.052 (2)
C11···H16a	3.19 (2)	C16···C17^i	4.052 (3)
O10···H19b	3.194 (14)	O10···O13	4.0693 (19)
O7···O15	3.1939 (16)	O15···C16	4.088 (3)
C18···H17c	3.196 (19)	C9···C12	4.088 (2)
O13···H16a	3.20 (2)	C14···C16	4.095 (3)
C11···O15	3.201 (2)	O10···C16	4.104 (2)
C9···C18	3.202 (3)	C6···C18	4.110 (3)
O8···H17a	3.203 (17)	C3···O8	4.127 (2)
C1···H18c	3.21 (2)	O7···C17	4.139 (2)
H14a···H16c	3.21 (3)	C5···C16	4.142 (3)
H16b···H6a	3.21 (3)	C12···C17	4.145 (2)
O8···H2a	3.208 (14)	C3···O20	4.151 (3)
O4···H18b	3.21 (2)	C2···C17	4.152 (2)
C14···H19b	3.211 (12)	C16···C18	4.163 (4)
C11···H16b	3.212 (16)	O7···O20	4.170 (2)
O7···H2a	3.214 (15)	C2···C9	4.172 (3)
H14c···H18a	3.22 (4)	C1···C19	4.175 (3)
O4···H11b	3.22 (2)	O4···C18	4.180 (3)
O4···H2a	3.225 (15)	O8···C11	4.201 (2)
O7···H16a	3.23 (2)	C14···C19	4.228 (4)
H14b···H17b	3.23 (2)	C2···C17	4.236 (3)
C9···H2a	3.226 (16)	C14···C18	4.242 (4)
O4···O20	3.2284 (19)	O4···C14	4.266 (3)
C3···C6	3.229 (2)	C3···C14	4.276 (3)
O8···H16b	3.231 (16)	C11···C14	4.280 (4)
O20···H18c	3.236 (18)	C14···C18	4.283 (4)
H14a···H19b	3.24 (3)	O10···O15	4.2850 (16)
O10···H17c	3.239 (18)	O8···O15	4.2902 (16)
O10···C19	3.240 (3)	C3···O10	4.296 (2)
O4···H19a	3.242 (16)	C14···C17	4.309 (3)
C2···C6	3.247 (3)	C17···O20	4.314 (3)
C12···H11b	3.249 (17)	C14···C16	4.329 (3)
C12···H18a	3.25 (2)	C18···C19	4.330 (3)
C19···H18c	3.267 (17)	O20···O20	4.346 (2)
O10···H11a	3.28 (2)	O20···O20	4.346 (2)
O7···H18b	3.28 (2)	C5···O20	4.348 (2)
C11···H20	3.29 (4)	O10···O20	4.350 (2)
H17b···H11b	3.31 (3)	O13···C18	4.354 (3)
C14···H16c	3.313 (18)	O4···O13	4.3569 (18)
C1···C18	3.314 (3)	C1···C18	4.387 (3)
H14a···H11b	3.32 (3)	O10···C12	4.388 (2)
C1···O15	3.319 (2)	C5···C19	4.388 (3)
H16c···H11b	3.32 (3)	C3···C16	4.390 (3)
C16···H11b	3.32 (2)	O4···C16	4.396 (2)
H18a···H20^i	3.32 (4)	C1···C11	4.409 (3)
C5···H18a	3.335 (19)	C2···C2	4.409 (3)
H18b···H16b	3.34 (3)	C12···C17	4.415 (3)
H6a···H20	3.34 (4)	C1···C14	4.416 (3)
H16c···H19b^i	3.34 (2)	C2···C19	4.420 (3)
C14···H18c	3.35 (2)	C2···C3	4.432 (3)
C6···O7	3.350 (2)	C11···C19	4.438 (3)
C12···H17c	3.356 (17)
O7—C1—O8	110.41 (13)	H11b—C11—H11a	110.0 (18)
O7—C1—C16	107.13 (14)	H11b—C11—C3	109.9 (11)
O7—C1—C2	111.45 (13)	H11c—C11—H11a	109.5 (16)
O8—C1—C16	106.74 (14)	H11c—C11—C3	108.5 (11)
O8—C1—C2	108.17 (11)	H11a—C11—C3	110.8 (11)
C16—C1—C2	112.83 (15)	O15—C12—O13	122.73 (15)
H2a—C2—C12	109.3 (8)	O15—C12—C2	126.32 (15)
H2a—C2—C3	107.2 (7)	O13—C12—C2	110.95 (15)
H2a—C2—C1	105.1 (7)	C12—O13—C14	115.12 (17)
C12—C2—C3	112.46 (13)	H14c—C14—H14a	111.5 (19)
C12—C2—C1	111.75 (12)	H14c—C14—H14b	107 (2)
C3—C2—C1	110.74 (13)	H14c—C14—O13	109.7 (16)
O4—C3—O10	103.86 (12)	H14a—C14—H14b	111.8 (17)
O4—C3—C11	110.20 (15)	H14a—C14—O13	105.9 (13)
O4—C3—C2	111.59 (12)	H14b—C14—O13	111.1 (10)
O10—C3—C11	109.58 (12)	H16c—C16—H16a	107.5 (17)
O10—C3—C2	106.60 (12)	H16c—C16—H16b	104.2 (14)
C11—C3—C2	114.40 (14)	H16c—C16—C1	109.7 (11)
C3—O4—C5	106.22 (12)	H16a—C16—H16b	111.8 (16)
O4—C5—C19	107.49 (13)	H16a—C16—C1	112.9 (9)
O4—C5—C6	107.66 (12)	H16b—C16—C1	110.3 (10)
O4—C5—C9	102.75 (13)	H17b—C17—H17c	107.3 (16)
C19—C5—C6	113.35 (16)	H17b—C17—H17a	109.5 (15)
C19—C5—C9	112.81 (14)	H17b—C17—C9	108.5 (11)
C6—C5—C9	111.98 (14)	H17c—C17—H17a	111.3 (15)
H6a—C6—O7	104.8 (8)	H17c—C17—C9	111.2 (10)
H6a—C6—C5	107.4 (7)	H17a—C17—C9	109.0 (11)
H6a—C6—C18	109.7 (9)	H18a—C18—H18c	113.0 (16)
O7—C6—C5	110.26 (15)	H18a—C18—H18b	105.5 (18)
O7—C6—C18	110.24 (16)	H18a—C18—C6	107.5 (13)
C5—C6—C18	114.05 (14)	H18c—C18—H18b	112.4 (16)
C1—O7—C6	116.55 (11)	H18c—C18—C6	109.7 (12)
C1—O8—C9	111.64 (11)	H18b—C18—C6	108.6 (11)
O10—C9—O8	108.51 (13)	H19a—C19—H19b	110.6 (10)
O10—C9—C17	109.53 (13)	H19a—C19—O20	109.6 (11)
O10—C9—C5	102.86 (12)	H19a—C19—C5	108.4 (9)
O8—C9—C17	106.83 (13)	H19b—C19—O20	103.0 (8)
O8—C9—C5	109.88 (11)	H19b—C19—C5	116.6 (8)
C17—C9—C5	118.88 (16)	O20—C19—C5	108.46 (15)
C9—O10—C3	102.37 (11)	H20—O20—C19	102 (2)
H11b—C11—H11c	108.1 (16)
O7—C1—C2—C3	75.55 (15)	C9—C5—C6—O7	−52.22 (17)
O7—C1—C2—C12	−50.68 (17)	C9—C5—C6—C18	72.4 (2)
O7—C1—C2—H2a	−169.1 (7)	C9—C5—C6—H6a	−165.8 (10)
O8—C1—C2—C3	−46.01 (19)	C19—C5—C6—O7	178.75 (14)
O8—C1—C2—C12	−172.24 (14)	C19—C5—C6—C18	−56.6 (2)
O8—C1—C2—H2a	69.4 (7)	C19—C5—C6—H6a	65.1 (10)
C16—C1—C2—C3	−163.86 (16)	O4—C5—C9—O8	−98.12 (12)
C16—C1—C2—C12	69.9 (2)	O4—C5—C9—O10	17.27 (13)
C16—C1—C2—H2a	−48.5 (7)	O4—C5—C9—C17	138.44 (13)
C2—C1—O7—C6	−88.64 (15)	C6—C5—C9—O8	17.14 (18)
O8—C1—O7—C6	31.62 (16)	C6—C5—C9—O10	132.53 (13)
C16—C1—O7—C6	147.49 (14)	C6—C5—C9—C17	−106.30 (16)
C2—C1—O8—C9	51.13 (18)	C19—C5—C9—O8	146.45 (13)
O7—C1—O8—C9	−71.07 (14)	C19—C5—C9—O10	−98.16 (14)
C16—C1—O8—C9	172.81 (15)	C19—C5—C9—C17	23.01 (18)
C2—C1—C16—H16a	52.4 (12)	O4—C5—C19—O20	65.54 (17)
C2—C1—C16—H16b	−73.5 (12)	O4—C5—C19—H19a	−175.6 (10)
C2—C1—C16—H16c	172.3 (13)	O4—C5—C19—H19b	−50.1 (8)
O7—C1—C16—H16a	175.4 (12)	C6—C5—C19—O20	−53.30 (18)
O7—C1—C16—H16b	49.5 (12)	C6—C5—C19—H19a	65.6 (10)
O7—C1—C16—H16c	−64.7 (13)	C6—C5—C19—H19b	−168.9 (8)
O8—C1—C16—H16a	−66.3 (12)	C9—C5—C19—O20	178.09 (13)
O8—C1—C16—H16b	167.8 (12)	C9—C5—C19—H19a	−63.0 (10)
O8—C1—C16—H16c	53.6 (13)	C9—C5—C19—H19b	62.5 (8)
C1—C2—C3—O4	−55.63 (17)	C5—C6—O7—C1	27.30 (18)
C1—C2—C3—O10	57.13 (17)	C18—C6—O7—C1	−99.51 (16)
C1—C2—C3—C11	178.41 (16)	H6a—C6—O7—C1	142.5 (8)
C12—C2—C3—O4	70.20 (17)	C5—C6—C18—H18a	−176.7 (15)
C12—C2—C3—O10	−177.04 (13)	C5—C6—C18—H18b	69.7 (11)
C12—C2—C3—C11	−55.8 (2)	C5—C6—C18—H18c	−53.5 (10)
H2a—C2—C3—O4	−169.7 (8)	O7—C6—C18—H18a	−52.0 (15)
H2a—C2—C3—O10	−56.9 (8)	O7—C6—C18—H18b	−165.7 (11)
H2a—C2—C3—C11	64.3 (8)	O7—C6—C18—H18c	71.2 (10)
C1—C2—C12—O13	−86.55 (17)	H6a—C6—C18—H18a	62.9 (17)
C1—C2—C12—O15	94.22 (19)	H6a—C6—C18—H18b	−50.8 (14)
C3—C2—C12—O13	148.17 (14)	H6a—C6—C18—H18c	−173.9 (13)
C3—C2—C12—O15	−31.1 (2)	C1—O8—C9—C5	42.23 (17)
H2a—C2—C12—O13	29.3 (7)	C1—O8—C9—O10	−69.52 (16)
H2a—C2—C12—O15	−149.9 (7)	C1—O8—C9—C17	172.46 (15)
C2—C3—O4—C5	77.98 (13)	C5—C9—O10—C3	−39.13 (13)
O10—C3—O4—C5	−36.48 (12)	O8—C9—O10—C3	77.24 (14)
C11—C3—O4—C5	−153.78 (12)	C17—C9—O10—C3	−166.48 (15)
C2—C3—O10—C9	−69.88 (15)	C5—C9—C17—H17a	−60.9 (13)
O4—C3—O10—C9	48.09 (13)	C5—C9—C17—H17b	179.9 (10)
C11—C3—O10—C9	165.81 (15)	C5—C9—C17—H17c	62.2 (12)
C2—C3—C11—H11a	67.0 (13)	O8—C9—C17—H17a	174.2 (13)
C2—C3—C11—H11b	−54.8 (11)	O8—C9—C17—H17b	55.0 (10)
C2—C3—C11—H11c	−172.7 (14)	O8—C9—C17—H17c	−62.7 (12)
O4—C3—C11—H11a	−59.6 (13)	O10—C9—C17—H17a	56.9 (14)
O4—C3—C11—H11b	178.6 (11)	O10—C9—C17—H17b	−62.3 (10)
O4—C3—C11—H11c	60.6 (14)	O10—C9—C17—H17c	179.9 (12)
O10—C3—C11—H11a	−173.3 (13)	C2—C12—O13—C14	−179.74 (16)
O10—C3—C11—H11b	64.9 (11)	O15—C12—O13—C14	−0.5 (2)
O10—C3—C11—H11c	−53.1 (14)	C12—O13—C14—H14a	−178.0 (12)
C3—O4—C5—C6	−106.86 (15)	C12—O13—C14—H14b	60.3 (14)
C3—O4—C5—C9	11.48 (12)	C12—O13—C14—H14c	−57.6 (16)
C3—O4—C5—C19	130.70 (14)	C5—C19—O20—H20	−179.7 (17)
O4—C5—C6—O7	60.00 (18)	H19a—C19—O20—H20	62.2 (19)
O4—C5—C6—C18	−175.34 (18)	H19b—C19—O20—H20	−55.5 (18)
O4—C5—C6—H6a	−53.6 (10)

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

(5eq)

Crystal data

C13H20O7	F(000) = 616
Mr = 288.3	Dx = 1.379 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54179 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 8.629 (6) Å	θ = 16.8–52.7°
b = 11.047 (7) Å	µ = 0.95 mm^−1
c = 14.573 (4) Å	T = 293 K
β = 91.66 (1)°	Irregular, colourless
V = 1388.6 (14) Å^3	0.6 × 0.5 × 0.3 mm
Z = 4

Data collection

CAD4 diffractometer	Rint = 0.025
Radiation source: Cu anode	θmax = 73.1°, θmin = 5.0°
Graphite monochromator	h = −10→10
ω/2θ scans	k = −13→13
5792 measured reflections	l = 0→18
2782 independent reflections	3 standard reflections every 400 reflections
2782 reflections with F^2 > .00 sig(F^2)	intensity decay: 5%

Refinement

Refinement on F^2	0 constraints
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.047	w = 1/[7.54σ^2(F^2)]
wR(F^2) = 0.063	(Δ/σ)max = 0.004
S = 1	Δρmax = 0.27 e Å^−3
2782 reflections	Δρmin = −0.20 e Å^−3
262 parameters	Extinction correction: Zachariasen, Eq22 p292 "Cryst. Comp." Munksgaard 1970
0 restraints	Extinction coefficient: 1517 (36)

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

	x	y	z	Uiso*/Ueq
O4	0.71347 (9)	0.32689 (10)	0.31261 (6)	0.0419 (5)
O7	0.42081 (9)	0.22533 (9)	0.32337 (6)	0.0400 (5)
O8	0.38370 (9)	0.42930 (10)	0.35447 (6)	0.0421 (5)
O10	0.63501 (11)	0.50011 (10)	0.37652 (6)	0.0442 (6)
O13	0.56252 (12)	0.17965 (12)	0.57358 (7)	0.0568 (7)
O15	0.69584 (13)	0.12555 (11)	0.45127 (8)	0.0665 (7)
O20	0.56389 (14)	0.43815 (15)	0.09358 (7)	0.0651 (8)
C1	0.41143 (14)	0.31336 (14)	0.39349 (10)	0.0382 (7)
C2	0.56438 (15)	0.31937 (14)	0.45261 (9)	0.0373 (7)
C3	0.69248 (14)	0.38261 (15)	0.39943 (9)	0.0394 (7)
C5	0.58992 (14)	0.37031 (15)	0.25275 (9)	0.0371 (7)
C6	0.47202 (14)	0.27002 (15)	0.23595 (9)	0.0389 (8)
C9	0.51729 (15)	0.47470 (15)	0.30873 (9)	0.0404 (8)
C11	0.8452 (2)	0.3929 (2)	0.45086 (13)	0.0563 (10)
C12	0.61582 (15)	0.19739 (16)	0.48890 (10)	0.0420 (8)
C14	0.6061 (3)	0.0677 (2)	0.61842 (18)	0.0705 (14)
C16	0.27196 (18)	0.2814 (2)	0.44988 (13)	0.0525 (10)
C17	0.4694 (2)	0.58994 (19)	0.26197 (13)	0.0551 (10)
C18	0.5307 (2)	0.1618 (2)	0.18573 (12)	0.0536 (10)
C19	0.67270 (18)	0.4118 (2)	0.16623 (10)	0.0512 (10)
H2	0.5438 (15)	0.3687 (14)	0.5039 (10)	0.052 (4)*
H6	0.3787 (14)	0.3062 (14)	0.2016 (9)	0.041 (4)*
H111	0.8846 (17)	0.3105 (18)	0.4615 (11)	0.061 (5)*
H112	0.8300 (18)	0.4344 (17)	0.5097 (11)	0.079 (6)*
H113	0.9177 (18)	0.4405 (18)	0.4152 (11)	0.073 (6)*
H141	0.715 (2)	0.056 (2)	0.6182 (13)	0.097 (7)*
H142	0.545 (2)	0.006 (2)	0.6012 (15)	0.117 (9)*
H143	0.592 (3)	0.083 (3)	0.6818 (17)	0.150 (11)*
H161	0.2866 (17)	0.1937 (16)	0.4669 (10)	0.062 (5)*
H162	0.1838 (16)	0.2892 (14)	0.4118 (9)	0.049 (4)*
H163	0.2731 (18)	0.3474 (16)	0.5003 (11)	0.072 (6)*
H171	0.390 (2)	0.573 (2)	0.2151 (12)	0.086 (6)*
H172	0.423 (2)	0.649 (2)	0.3022 (13)	0.100 (8)*
H173	0.563 (2)	0.631 (2)	0.2331 (12)	0.095 (7)*
H181	0.4562 (16)	0.0958 (16)	0.1818 (10)	0.057 (5)*
H182	0.6275 (17)	0.1339 (16)	0.2134 (10)	0.061 (5)*
H183	0.5545 (18)	0.1886 (17)	0.1236 (11)	0.067 (5)*
H191	0.7436 (16)	0.4878 (15)	0.1807 (10)	0.058 (5)*
H192	0.7493 (18)	0.3469 (16)	0.1539 (11)	0.066 (5)*
H20	0.594 (3)	0.508 (3)	0.0672 (16)	0.141 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O4	0.0349 (4)	0.0558 (8)	0.0349 (5)	0.0045 (5)	0.0009 (3)	−0.0027 (6)
O7	0.0429 (5)	0.0404 (7)	0.0369 (5)	−0.0051 (4)	0.0056 (4)	−0.0053 (6)
O8	0.0390 (4)	0.0409 (7)	0.0467 (6)	0.0064 (4)	0.0077 (4)	−0.0005 (6)
O10	0.0530 (5)	0.0388 (6)	0.0403 (5)	−0.0068 (5)	−0.0057 (4)	−0.0008 (6)
O13	0.0764 (7)	0.0465 (8)	0.0478 (6)	0.0059 (6)	0.0083 (5)	0.0116 (6)
O15	0.0807 (7)	0.0549 (8)	0.0642 (7)	0.0250 (7)	0.0060 (6)	−0.0060 (8)
O20	0.0767 (7)	0.0787 (11)	0.0394 (6)	−0.0082 (8)	−0.0042 (5)	0.0092 (8)
C1	0.0370 (6)	0.0365 (9)	0.0415 (7)	0.0017 (6)	0.0070 (5)	−0.0034 (8)
C2	0.0444 (7)	0.0358 (9)	0.0318 (7)	0.0006 (6)	0.0044 (6)	−0.0057 (8)
C3	0.0405 (6)	0.0422 (9)	0.0354 (7)	−0.0030 (6)	−0.0014 (5)	−0.0034 (9)
C5	0.0358 (6)	0.0433 (10)	0.0323 (6)	−0.0000 (6)	0.0001 (5)	−0.0012 (8)
C6	0.0394 (6)	0.0437 (10)	0.0335 (7)	0.0005 (6)	−0.0010 (5)	−0.0017 (8)
C9	0.0422 (6)	0.0398 (10)	0.0390 (7)	−0.0023 (6)	−0.0020 (6)	−0.0002 (8)
C11	0.0500 (8)	0.0629 (13)	0.0551 (10)	−0.0120 (9)	−0.0149 (8)	0.0045 (12)
C12	0.0454 (7)	0.0398 (9)	0.0407 (8)	0.0000 (7)	−0.0027 (6)	−0.0057 (9)
C14	0.0826 (14)	0.0500 (13)	0.0779 (15)	−0.0078 (11)	−0.0132 (12)	0.0250 (13)
C16	0.0431 (7)	0.0592 (13)	0.0560 (10)	−0.0009 (8)	0.0173 (7)	−0.0010 (11)
C17	0.0683 (10)	0.0434 (11)	0.0530 (10)	0.0031 (9)	−0.0077 (9)	0.0039 (11)
C18	0.0678 (10)	0.0503 (11)	0.0427 (9)	0.0043 (9)	0.0033 (8)	−0.0134 (10)
C19	0.0507 (8)	0.0669 (14)	0.0361 (8)	−0.0068 (9)	0.0052 (6)	0.0037 (10)

Geometric parameters (Å, º)

O4—C3	1.4233 (17)	C5—C9	1.555 (2)
O4—C5	1.4400 (16)	C6—H6	1.018 (13)
O7—C1	1.4146 (18)	C6—C18	1.497 (3)
O7—C6	1.4472 (16)	C9—C17	1.497 (3)
O8—C1	1.419 (2)	C11—H113	0.978 (17)
O8—C9	1.4385 (17)	C11—H111	0.98 (2)
O10—C9	1.4242 (17)	C11—H112	0.985 (17)
O10—C3	1.426 (2)	C14—H142	0.90 (2)
O13—C12	1.3438 (18)	C14—H141	0.94 (2)
O13—C14	1.443 (3)	C14—H143	0.95 (3)
O15—C12	1.196 (2)	C16—H162	0.932 (14)
O20—H20	0.91 (3)	C16—H161	1.007 (17)
O20—C19	1.425 (2)	C16—H163	1.035 (17)
C1—C16	1.518 (2)	C17—H172	0.97 (2)
C1—C2	1.557 (2)	C17—H171	0.972 (18)
C2—H2	0.946 (15)	C17—H173	1.03 (2)
C2—C12	1.510 (2)	C18—H182	0.967 (15)
C2—C3	1.536 (2)	C18—H181	0.972 (16)
C3—C11	1.501 (2)	C18—H183	0.980 (17)
C5—C6	1.519 (2)	C19—H192	0.995 (17)
C5—C19	1.537 (2)	C19—H191	1.057 (16)
H141···H143	1.46 (3)	C3···H163	3.330 (18)
H142···H143	1.50 (4)	H172···H181^ii	3.34 (2)
H171···H172	1.54 (3)	C2···H162	3.337 (14)
H182···H183	1.56 (2)	C14···H191	3.339 (15)
H161···H162	1.58 (2)	C11···H113	3.339 (17)
H141···H142	1.58 (3)	C17···H6	3.342 (15)
H181···H183	1.59 (2)	H161···H183	3.34 (2)
H181···H182	1.59 (2)	C14···H172	3.35 (2)
H112···H113	1.59 (2)	O20···C18	3.351 (3)
H191···H192	1.61 (2)	H142···H181	3.36 (3)
H172···H173	1.61 (3)	O7···C14	3.356 (3)
H111···H112	1.62 (3)	C6···H141	3.37 (2)
H111···H113	1.62 (3)	C16···H111	3.367 (15)
H162···H163	1.62 (2)	C9···H192	3.370 (16)
H171···H173	1.64 (3)	H111···H20	3.37 (4)
H161···H163	1.77 (2)	O13···H142	3.38 (2)
C19···H20	1.90 (3)	C12···H20	3.38 (3)
O13···H143	1.91 (3)	C2···H113	3.388 (17)
O13···H142	1.97 (3)	H163···H182	3.39 (2)
O13···H141	1.99 (2)	H171···H181^ii	3.39 (2)
C12···H2	2.005 (16)	O10···H183	3.393 (17)
C1···H162	2.008 (14)	C5···H181	3.395 (17)
O7···H6	2.011 (13)	C12···H163	3.398 (16)
C6···H183	2.016 (17)	C17···H141	3.40 (2)
C1···H163	2.024 (16)	O4···H183	3.404 (17)
C3···H2	2.025 (14)	H111···H163	3.41 (2)
C3···H111	2.028 (16)	H111···H181^i	3.41 (2)
C1···H161	2.029 (16)	C3···C19	3.413 (2)
C5···H192	2.037 (16)	O7···H143	3.41 (3)
C9···H171	2.04 (2)	C11···H112	3.425 (17)
C1···H2	2.040 (14)	C6···H171	3.43 (2)
C6···H182	2.048 (17)	H162···H173	3.43 (2)
O20···H191	2.050 (14)	H113···H163	3.43 (2)
C3···H112	2.051 (16)	C3···H191	3.434 (15)
C3···H113	2.053 (16)	O7···H141	3.44 (2)
O20···H192	2.066 (16)	H143···H182	3.44 (3)
C5···H6	2.074 (13)	H181···H191	3.44 (2)
H191···H20	2.08 (3)	C17···H2	3.447 (14)
C18···H6	2.082 (14)	O15···H173	3.448 (18)
C6···H181	2.083 (17)	C11···H181	3.448 (16)
C9···H172	2.09 (2)	C19···H182	3.449 (16)
C9···H173	2.09 (2)	H141···H20^i	3.45 (3)
C5···H191	2.151 (15)	H2···H162	3.46 (2)
C3···C9	2.225 (2)	C18···H163	3.466 (16)
O13···O15	2.2308 (17)	C6···H191	3.470 (16)
O4···O10	2.2415 (18)	C11···H181^i	3.474 (15)
O15···H20	2.25 (2)	O15···H192	3.477 (18)
C3···C5	2.2937 (19)	H142···H171^i	3.48 (3)
O8···O10	2.3189 (19)	H142···H182	3.48 (3)
H6···H183	2.32 (2)	C18···H111	3.482 (15)
O7···O8	2.322 (2)	C14···H181	3.482 (16)
O13···H2	2.325 (16)	C5···H172	3.48 (2)
O10···C5	2.3280 (18)	O8···H181^ii	3.489 (15)
O13···C2	2.344 (2)	C19···H142	3.49 (2)
H2···H163	2.35 (2)	O15···C14	3.496 (3)
O4···C19	2.348 (2)	H111···H173	3.50 (3)
O7···C18	2.350 (2)	O15···H182	3.501 (14)
O4···C9	2.352 (2)	C18···H143	3.51 (3)
O4···H192	2.353 (16)	O8···H143	3.51 (2)
O7···C16	2.360 (2)	C12···H172	3.51 (2)
O8···C17	2.360 (2)	O13···C17	3.512 (3)
H173···H191	2.37 (3)	H2···H163	3.51 (2)
C1···C9	2.367 (2)	C14···H142	3.51 (2)
O8···C16	2.368 (2)	C17···H182	3.520 (15)
O10···C2	2.372 (2)	H113···H183^i	3.53 (2)
C12···C14	2.373 (3)	O10···C6	3.531 (2)
O10···C17	2.382 (2)	H6···H20	3.53 (3)
H6···H141	2.38 (2)	O15···H143	3.53 (3)
O4···C11	2.398 (2)	O10···C18	3.534 (3)
O10···C11	2.399 (2)	O7···H172	3.541 (18)
O8···C2	2.4128 (18)	H6···H162	3.54 (2)
O7···C5	2.417 (2)	C1···H142	3.54 (3)
C1···C6	2.417 (2)	C16···H113	3.549 (17)
O4···C6	2.418 (2)	C6···C17	3.555 (3)
O15···C2	2.423 (2)	C9···H182	3.556 (16)
O8···C5	2.4375 (18)	C11···H183	3.556 (19)
H6···H181	2.44 (2)	C3···C17	3.569 (3)
O20···C5	2.4419 (18)	O13···H111	3.570 (16)
O7···H161	2.445 (15)	O10···C16	3.571 (3)
O4···C2	2.4447 (17)	H112···H183	3.57 (3)
O7···C2	2.4547 (17)	C9···C11	3.574 (3)
H183···H192	2.46 (2)	C17···H162^ii	3.579 (14)
H182···H191	2.47 (2)	H162···H172	3.58 (2)
O8···H162	2.480 (15)	C16···H171	3.58 (2)
H141···H171^i	2.49 (3)	H142···H161	3.58 (3)
H113···H181	2.49 (2)	C2···H172	3.589 (19)
O10···H2	2.502 (15)	C5···C11	3.589 (2)
H20···H20	2.51 (3)	O13···C3	3.590 (2)
O15···H191	2.519 (16)	C11···H182	3.592 (17)
O8···H163	2.523 (16)	H2···H113	3.60 (2)
C6···C9	2.523 (3)	C3···H182	3.601 (17)
C3···C12	2.525 (2)	C6···C16	3.609 (2)
O7···H181	2.537 (16)	C19···H143	3.62 (2)
C1···C3	2.542 (2)	C9···H20	3.62 (2)
H192···H20	2.55 (3)	H172···H192	3.62 (3)
C5···C18	2.548 (3)	C12···H191	3.621 (16)
O7···H162	2.548 (14)	O4···O20	3.6231 (17)
O15···H141	2.551 (19)	O15···H161	3.624 (15)
C2···C11	2.557 (3)	O7···O10	3.626 (2)
C2···C16	2.557 (3)	C6···H162	3.629 (14)
C1···C12	2.558 (2)	C16···H142	3.63 (3)
O8···H172	2.57 (2)	C2···H2	3.631 (16)
C6···C19	2.567 (3)	C1···C18	3.634 (3)
O10···H163	2.570 (17)	C3···H192	3.647 (16)
C12···H141	2.57 (2)	C1···C17	3.649 (3)
H112···H163	2.57 (3)	O4···C17	3.652 (3)
H2···H112	2.57 (2)	O10···C2	3.659 (2)
O10···H113	2.574 (16)	O20···H111	3.671 (18)
O8···H171	2.58 (2)	C9···C16	3.678 (3)
O4···H111	2.595 (15)	O4···H182	3.682 (18)
O8···C6	2.595 (2)	C18···H173	3.685 (19)
C9···C19	2.599 (2)	C6···H172	3.687 (19)
O4···H113	2.601 (17)	C18···H142	3.69 (2)
O10···H173	2.604 (19)	O13···H173	3.69 (2)
O8···H6	2.610 (13)	C5···H2	3.694 (14)
O15···H111	2.615 (18)	C2···C14	3.694 (3)
O13···H172	2.62 (2)	O15···H112	3.695 (19)
O15···H142	2.63 (2)	O13···H191	3.699 (15)
O8···H2	2.632 (14)	O20···C16	3.703 (3)
O10···H112	2.634 (16)	O8···H141	3.704 (18)
O7···H182	2.634 (15)	C5···H113	3.718 (16)
C16···H2	2.636 (13)	C6···H143	3.72 (2)
O4···H191	2.637 (16)	C3···H2	3.722 (15)
C5···C17	2.645 (3)	O15···H161	3.725 (17)
C2···H163	2.645 (16)	O10···C12	3.729 (3)
O15···C14	2.655 (3)	C17···H143	3.74 (3)
O10···H172	2.67 (2)	C11···C18	3.749 (3)
O4···H182	2.669 (17)	C14···H161	3.750 (16)
H163···H183	2.67 (2)	C14···H2	3.751 (16)
C12···H111	2.675 (16)	O4···H191	3.765 (17)
C1···C5	2.675 (2)	O8···C19	3.765 (2)
C9···H6	2.688 (14)	C9···H113	3.766 (16)
C5···H182	2.696 (18)	O8···C12	3.766 (2)
O20···H6	2.702 (14)	C16···H6	3.770 (13)
H111···H162	2.71 (2)	C9···H141	3.772 (19)
H112···H181^i	2.73 (2)	C6···H20	3.77 (3)
H182···H192	2.73 (2)	O13···H112	3.773 (18)
C2···H112	2.729 (17)	C11···H163	3.775 (15)
C2···C9	2.731 (2)	O4···H173	3.78 (2)
C19···H183	2.734 (19)	C1···H112	3.776 (18)
O20···H20	2.74 (2)	C11···C18^i	3.785 (3)
H111···H183^i	2.74 (2)	C17···H181^ii	3.786 (14)
C9···H191	2.744 (15)	C12···H6^i	3.787 (13)
C11···H2	2.748 (13)	C2···H142	3.79 (3)
C12···H142	2.76 (2)	O13···C19	3.798 (3)
H173···H182	2.76 (2)	O10···H181	3.802 (14)
C5···H183	2.763 (18)	O15···O20^i	3.808 (2)
C2···H111	2.764 (15)	O7···C19	3.808 (2)
H6···H143	2.77 (3)	C3···H173	3.81 (2)
O10···H2	2.770 (14)	C12···C14	3.810 (3)
O4···O7	2.772 (2)	O10···H192	3.814 (16)
O8···C3	2.774 (2)	C9···H163	3.815 (16)
H112···H113	2.78 (2)	O20···H162	3.815 (15)
C2···H161	2.783 (16)	C11···C11	3.816 (3)
O20···H171	2.78 (2)	C1···H182	3.818 (16)
C19···H173	2.79 (2)	C9···H163	3.819 (16)
H161···H192	2.79 (2)	O20···H182	3.820 (17)
O7···H142	2.79 (3)	C5···H182	3.821 (17)
O20···H183	2.79 (2)	C5···H141	3.82 (2)
H173···H20	2.79 (3)	C14···C19	3.831 (4)
C1···H6	2.804 (13)	C1···H2	3.833 (16)
H113···H183	2.81 (3)	O7···O13	3.8453 (16)
O13···H161	2.810 (15)	O4···H181	3.851 (16)
C18···H192	2.830 (17)	C14···H20	3.85 (2)
H142···H161	2.84 (3)	O7···C17	3.857 (3)
C6···H192	2.836 (16)	C6···H161	3.861 (15)
H2···H172	2.84 (2)	C19···H163	3.862 (17)
O10···C1	2.840 (2)	C16···H141	3.86 (2)
H113···H162	2.84 (2)	C6···H142	3.87 (2)
H143···H181	2.85 (3)	O13···C11	3.867 (3)
C12···H161	2.850 (15)	O15···H143	3.87 (3)
C19···H6	2.853 (13)	C1···H171	3.87 (2)
H112···H183^i	2.86 (2)	C9···H162	3.871 (15)
H113···H182	2.86 (2)	C11···C16	3.883 (3)
C5···H171	2.87 (2)	C17···H6^ii	3.886 (14)
H6···H182	2.87 (2)	C3···C16	3.887 (3)
O10···H182	2.873 (16)	C3···H182	3.890 (16)
H142···H191	2.87 (3)	C6···H171	3.89 (2)
O7···C9	2.887 (3)	C9···C18	3.897 (3)
C18···H113	2.894 (19)	O20···H163	3.899 (17)
O4···C1	2.895 (2)	O20···H141	3.90 (2)
O15···H142	2.90 (2)	O7···H191	3.909 (16)
C17···H191	2.905 (15)	C17···H192	3.909 (17)
C5···H173	2.91 (2)	C1···C11	3.912 (3)
H171···H20	2.91 (3)	C12···H113	3.913 (18)
O20···C6	2.912 (2)	C14···H182	3.914 (16)
O7···C12	2.9173 (18)	C16···C19	3.923 (3)
C12···H142	2.93 (2)	C18···H172	3.924 (18)
O15···C3	2.938 (3)	C17···H143	3.93 (2)
O20···H173	2.95 (2)	C5···C12	3.937 (2)
H6···H171	2.95 (3)	C6···C12	3.938 (2)
C14···H6^i	2.962 (13)	C1···H181	3.938 (16)
H143···H172	2.97 (4)	C1···H172	3.94 (2)
H2···H161	2.98 (2)	C9···H112	3.950 (16)
C2···C5	2.981 (2)	C2···H6	3.954 (13)
O4···H173	2.99 (2)	O4···H143	3.95 (2)
O13···H192	2.991 (16)	O10···H6	3.956 (13)
C11···C12	2.992 (3)	C19···H172	3.96 (2)
H2···H2	3.00 (2)	C16···H20	3.96 (3)
C17···C19	3.006 (3)	O4···C17	3.962 (3)
O4···C18	3.011 (2)	C5···H111	3.963 (15)
O4···O15	3.012 (2)	C3···H163	3.964 (16)
O15···O20	3.015 (2)	O10···C1	3.965 (2)
H142···H142	3.03 (3)	O8···C2	3.967 (2)
H141···H161	3.03 (3)	C17···H192	3.968 (17)
O10···H191	3.033 (15)	C19···H181	3.969 (17)
C18···C19	3.038 (3)	C2···H141	3.97 (2)
O20···H141	3.05 (2)	O15···C6	3.971 (2)
H143···H192	3.07 (3)	C6···C14	3.975 (3)
O20···H161	3.071 (16)	O20···C14	3.978 (4)
H162···H171	3.08 (3)	C3···H172	3.98 (2)
C9···H2	3.079 (14)	O10···H192	3.987 (18)
O4···C12	3.079 (2)	C3···H6	3.988 (13)
H2···H111	3.09 (2)	C2···H163	3.991 (18)
O8···H2	3.091 (15)	C12···H162	3.993 (14)
C12···H143	3.09 (3)	C5···H173	3.99 (2)
O15···H2	3.095 (15)	O10···O13	4.003 (3)
O7···C3	3.097 (2)	O15···H6^i	4.003 (13)
O20···C17	3.101 (3)	O8···O10	4.0050 (17)
C5···H20	3.11 (3)	C18···H112	4.009 (17)
H113···H113	3.11 (2)	C19···H141	4.01 (2)
H143···H191	3.11 (3)	C1···H171	4.01 (2)
H163···H192	3.11 (2)	O8···C11	4.017 (2)
C19···H171	3.12 (2)	C3···H173	4.02 (2)
H143···H171^i	3.12 (3)	C11···C16	4.018 (4)
H6···H172	3.13 (2)	C14···C18	4.020 (3)
O8···H112	3.129 (17)	C16···H113	4.021 (18)
C11···H163	3.134 (18)	C11···H173	4.04 (2)
H113···H163	3.14 (2)	O15···C16	4.042 (3)
H142···H192	3.14 (3)	O15···C5	4.045 (2)
O4···O8	3.138 (2)	O13···O15	4.052 (3)
C12···C16	3.145 (3)	O8···C18	4.070 (3)
O15···C19	3.147 (3)	O15···C18	4.105 (2)
H161···H20	3.17 (3)	C14···C17^i	4.106 (4)
O7···O15	3.173 (2)	C9···C12	4.108 (3)
C19···H182	3.173 (18)	C3···C18	4.115 (3)
C11···H183^i	3.185 (16)	C16···C18	4.118 (3)
O7···H183	3.189 (17)	O10···C16	4.122 (3)
C14···H171^i	3.193 (19)	C14···C16	4.127 (4)
C17···H20	3.19 (2)	O8···C14	4.135 (3)
O20···C9	3.198 (2)	C14···C14	4.140 (4)
O8···H161	3.199 (17)	O13···C14	4.144 (3)
O7···H171	3.203 (19)	C2···C17	4.146 (3)
C11···H162	3.204 (15)	C5···C16	4.148 (3)
O7···H163	3.207 (16)	O7···C17	4.150 (3)
C16···H183	3.212 (16)	O8···O20	4.1503 (18)
C12···H112	3.214 (18)	C3···C18	4.165 (3)
O20···O20	3.2166 (19)	O20···C12	4.181 (3)
O10···H171	3.219 (18)	C1···C19	4.203 (2)
O4···H2	3.220 (14)	O8···C11	4.204 (3)
O15···C11	3.223 (3)	O10···O20	4.2072 (18)
O7···H2	3.224 (14)	O8···C3	4.213 (2)
O10···H111	3.225 (17)	C1···C14	4.216 (4)
C18···H112	3.233 (16)	C14···C17	4.223 (4)
O4···H112	3.241 (16)	O13···C6^i	4.232 (3)
O10···C19	3.241 (2)	C2···C9	4.232 (2)
H171···H191	3.25 (2)	C16···C17	4.239 (3)
O13···C16	3.246 (2)	O13···C9	4.250 (3)
O13···C1	3.251 (2)	C2···C18	4.263 (3)
H141···H20	3.25 (3)	C2···C17	4.297 (3)
C3···C6	3.253 (2)	C6···C17	4.298 (3)
H112···H162	3.26 (2)	O7···O20	4.302 (2)
O13···H6^i	3.264 (13)	C18···C19	4.303 (3)
O8···H173	3.26 (2)	O10···O15	4.307 (3)
O13···H163	3.264 (16)	O4···C18	4.308 (3)
C14···H192	3.275 (16)	C12···C19	4.317 (3)
O4···H6	3.278 (13)	C3···C16	4.319 (3)
C2···C6	3.279 (2)	O15···C17	4.322 (3)
C9···H2	3.288 (15)	O10···O10	4.3436 (18)
C14···H161	3.288 (17)	C6···C14	4.354 (4)
H112···H112	3.29 (2)	O4···O13	4.3696 (17)
H173···H192	3.30 (3)	C11···C19	4.371 (3)
H161···H171	3.30 (2)	C2···C2	4.377 (3)
O15···C1	3.304 (2)	O20···C12	4.379 (3)
C16···H192	3.305 (16)	O4···C16	4.383 (3)
C19···H161	3.306 (16)	C12···C17	4.404 (3)
C16···H112	3.317 (19)	C9···C18	4.413 (3)
H162···H183	3.32 (2)	C14···C16	4.417 (3)
H6···H192	3.32 (2)	C2···C19	4.423 (2)
C18···H191	3.325 (15)	C17···C18	4.431 (4)
C3—O4—C5	106.46 (10)	C17—C9—C5	120.15 (13)
C1—O7—C6	115.26 (12)	H113—C11—H111	111.0 (14)
C1—O8—C9	111.86 (10)	H113—C11—H112	108.4 (15)
C9—O10—C3	102.66 (11)	H113—C11—C3	110.0 (9)
C12—O13—C14	116.69 (15)	H111—C11—H112	110.4 (14)
H20—O20—C19	107.5 (14)	H111—C11—C3	107.7 (9)
O7—C1—O8	110.10 (11)	H112—C11—C3	109.4 (9)
O7—C1—C16	107.10 (13)	O15—C12—O13	122.82 (16)
O7—C1—C2	111.33 (11)	O15—C12—C2	126.85 (14)
O8—C1—C16	107.43 (12)	O13—C12—C2	110.30 (13)
O8—C1—C2	108.29 (11)	H142—C14—H141	118 (2)
C16—C1—C2	112.52 (13)	H142—C14—H143	109 (2)
H2—C2—C12	107.3 (9)	H142—C14—O13	112.5 (15)
H2—C2—C3	106.9 (9)	H141—C14—H143	100.5 (18)
H2—C2—C1	106.7 (8)	H141—C14—O13	110.9 (13)
C12—C2—C3	111.97 (12)	H143—C14—O13	104.1 (18)
C12—C2—C1	113.07 (12)	H162—C16—H161	109.3 (13)
C3—C2—C1	110.56 (11)	H162—C16—H163	110.4 (13)
O4—C3—O10	103.76 (10)	H162—C16—C1	107.6 (9)
O4—C3—C11	110.12 (12)	H161—C16—H163	120.3 (13)
O4—C3—C2	111.33 (12)	H161—C16—C1	105.1 (9)
O10—C3—C11	110.02 (14)	H163—C16—C1	103.2 (9)
O10—C3—C2	106.36 (11)	H172—C17—H171	105.0 (16)
C11—C3—C2	114.62 (13)	H172—C17—H173	107.1 (17)
O4—C5—C6	109.59 (13)	H172—C17—C9	114.1 (12)
O4—C5—C19	104.05 (11)	H171—C17—H173	110.2 (15)
O4—C5—C9	103.41 (10)	H171—C17—C9	109.5 (13)
C6—C5—C19	114.22 (12)	H173—C17—C9	110.8 (11)
C6—C5—C9	110.31 (11)	H182—C18—H181	110.3 (14)
C19—C5—C9	114.40 (14)	H182—C18—H183	106.2 (13)
H6—C6—O7	108.1 (7)	H182—C18—C6	110.6 (10)
H6—C6—C18	110.3 (8)	H181—C18—H183	109.1 (13)
H6—C6—C5	108.0 (8)	H181—C18—C6	113.3 (9)
O7—C6—C18	105.91 (14)	H183—C18—C6	107.1 (11)
O7—C6—C5	109.09 (10)	H192—C19—H191	103.0 (13)
C18—C6—C5	115.26 (13)	H192—C19—O20	116.1 (9)
O10—C9—O8	108.20 (11)	H192—C19—C5	105.1 (10)
O10—C9—C17	109.28 (13)	H191—C19—O20	110.6 (8)
O10—C9—C5	102.70 (10)	H191—C19—C5	110.7 (8)
O8—C9—C17	107.05 (12)	O20—C19—C5	111.02 (12)
O8—C9—C5	108.97 (12)
C5—O4—C3—O10	−35.43 (12)	C1—C2—C12—O15	88.02 (18)
C5—O4—C3—C2	78.58 (14)	C3—C2—C12—O13	140.41 (12)
C5—O4—C3—C11	−153.15 (14)	C3—C2—C12—O15	−37.7 (2)
C3—O4—C5—C6	−106.84 (12)	H2—C2—C12—O13	23.4 (8)
C3—O4—C5—C9	10.78 (13)	H2—C2—C12—O15	−154.7 (8)
C3—O4—C5—C19	130.61 (13)	O4—C3—C11—H111	−62.2 (10)
C6—O7—C1—O8	27.26 (13)	O4—C3—C11—H112	177.8 (11)
C6—O7—C1—C2	−92.85 (13)	O4—C3—C11—H113	58.8 (12)
C6—O7—C1—C16	143.76 (12)	O10—C3—C11—H111	−176.0 (10)
C1—O7—C6—C5	34.40 (14)	O10—C3—C11—H112	64.0 (11)
C1—O7—C6—C18	159.02 (11)	O10—C3—C11—H113	−54.9 (12)
C1—O7—C6—H6	−82.8 (9)	C2—C3—C11—H111	64.2 (10)
C9—O8—C1—O7	−70.82 (12)	C2—C3—C11—H112	−55.8 (12)
C9—O8—C1—C2	51.11 (14)	C2—C3—C11—H113	−174.7 (12)
C9—O8—C1—C16	172.88 (12)	O4—C5—C6—O7	54.51 (14)
C1—O8—C9—O10	−68.37 (14)	O4—C5—C6—C18	−64.43 (15)
C1—O8—C9—C5	42.59 (13)	O4—C5—C6—H6	171.7 (8)
C1—O8—C9—C17	173.96 (12)	C9—C5—C6—O7	−58.70 (14)
C9—O10—C3—O4	46.91 (11)	C9—C5—C6—C18	−177.65 (12)
C9—O10—C3—C2	−70.62 (12)	C9—C5—C6—H6	58.5 (8)
C9—O10—C3—C11	164.69 (12)	C19—C5—C6—O7	170.78 (12)
C3—O10—C9—O8	76.50 (12)	C19—C5—C6—C18	51.84 (18)
C3—O10—C9—C5	−38.65 (12)	C19—C5—C6—H6	−72.0 (8)
C3—O10—C9—C17	−167.28 (12)	O4—C5—C9—O8	−97.30 (12)
C14—O13—C12—O15	−0.2 (2)	O4—C5—C9—O10	17.28 (13)
C14—O13—C12—C2	−178.37 (14)	O4—C5—C9—C17	138.77 (13)
C12—O13—C14—H141	52.4 (13)	C6—C5—C9—O8	19.81 (14)
C12—O13—C14—H142	−82.9 (16)	C6—C5—C9—O10	134.39 (11)
C12—O13—C14—H143	159.7 (15)	C6—C5—C9—C17	−104.12 (15)
H20—O20—C19—C5	136.0 (17)	C19—C5—C9—O8	150.23 (11)
H20—O20—C19—H191	12.7 (19)	C19—C5—C9—O10	−95.19 (13)
H20—O20—C19—H192	−104 (2)	C19—C5—C9—C17	26.30 (18)
O7—C1—C2—C3	74.26 (16)	O4—C5—C19—O20	169.91 (14)
O7—C1—C2—C12	−52.18 (15)	O4—C5—C19—H191	−66.9 (9)
O7—C1—C2—H2	−169.8 (10)	O4—C5—C19—H192	43.7 (10)
O8—C1—C2—C3	−46.91 (15)	C6—C5—C19—O20	50.5 (2)
O8—C1—C2—C12	−173.35 (11)	C6—C5—C19—H191	173.7 (9)
O8—C1—C2—H2	69.0 (10)	C6—C5—C19—H192	−75.8 (10)
C16—C1—C2—C3	−165.50 (14)	C9—C5—C19—O20	−78.00 (17)
C16—C1—C2—C12	68.06 (17)	C9—C5—C19—H191	45.2 (9)
C16—C1—C2—H2	−49.6 (10)	C9—C5—C19—H192	155.7 (10)
O7—C1—C16—H161	51.9 (9)	O7—C6—C18—H181	53.1 (10)
O7—C1—C16—H162	−64.5 (10)	O7—C6—C18—H182	−71.2 (10)
O7—C1—C16—H163	178.8 (9)	O7—C6—C18—H183	173.4 (10)
O8—C1—C16—H161	170.1 (9)	C5—C6—C18—H181	173.8 (10)
O8—C1—C16—H162	53.8 (10)	C5—C6—C18—H182	49.4 (10)
O8—C1—C16—H163	−63.0 (9)	C5—C6—C18—H183	−65.9 (10)
C2—C1—C16—H161	−70.8 (9)	H6—C6—C18—H181	−63.5 (13)
C2—C1—C16—H162	172.9 (10)	H6—C6—C18—H182	172.1 (13)
C2—C1—C16—H163	56.1 (9)	H6—C6—C18—H183	56.8 (13)
C1—C2—C3—O4	−54.17 (16)	O8—C9—C17—H171	−63.8 (11)
C1—C2—C3—O10	58.21 (14)	O8—C9—C17—H172	53.5 (12)
C1—C2—C3—C11	−179.99 (15)	O8—C9—C17—H173	174.5 (11)
C12—C2—C3—O4	72.88 (14)	O10—C9—C17—H171	179.3 (11)
C12—C2—C3—O10	−174.74 (11)	O10—C9—C17—H172	−63.4 (12)
C12—C2—C3—C11	−52.94 (18)	O10—C9—C17—H173	57.5 (11)
H2—C2—C3—O4	−169.9 (9)	C5—C9—C17—H171	61.1 (11)
H2—C2—C3—O10	−57.5 (9)	C5—C9—C17—H172	178.4 (12)
H2—C2—C3—C11	64.3 (9)	C5—C9—C17—H173	−60.7 (11)
C1—C2—C12—O13	−93.91 (14)

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+1/2, y+1/2, −z+1/2.

(6)

Crystal data

C14H22O6	Z = 2
Mr = 286.32	F(000) = 308
Triclinic, P1	Dx = 1.347 Mg m^−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54179 Å
a = 8.070 (2) Å	Cell parameters from 25 reflections
b = 8.753 (2) Å	θ = 10.2–18.9°
c = 11.084 (3) Å	µ = 0.88 mm^−1
α = 77.03 (2)°	T = 293 K
β = 72.27 (2)°	Irregular, colourless
γ = 73.14 (2)°	0.60 × 0.50 × 0.36 mm
V = 705.7 (3) Å^3

Data collection

CAD4 diffractometer	θmax = 74.7°, θmin = 4.2°
ω/2θ scans	h = −9→10
2934 measured reflections	k = −9→10
2669 independent reflections	l = 0→13
2669 reflections with F^2 > .00 sig(F^2)	3 standard reflections every 400 reflections
Rint = 0.012	intensity decay: 2%

Refinement

Refinement on F^2	0 constraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.072	w = 1/(11.2σ^2(F^2))
wR(F^2) = 0.075	(Δ/σ)max = 0.019
S = 1.00	Δρmax = 0.40 e Å^−3
2669 reflections	Δρmin = −0.36 e Å^−3
266 parameters	Extinction correction: Zachariasen, Eq22 p292 "Cryst. Comp." Munksgaard 1970
0 restraints	Extinction coefficient: 723 (45)

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

	x	y	z	Uiso*/Ueq
O4	0.3532 (2)	0.65090 (19)	0.33419 (16)	0.0392 (17)
O7	0.6344 (2)	0.7754 (2)	0.17963 (17)	0.0415 (18)
O8	0.4787 (2)	0.76057 (19)	0.03985 (17)	0.0403 (17)
O10	0.2767 (2)	0.6099 (2)	0.16687 (18)	0.045 (2)
O13	0.7868 (3)	0.2705 (2)	0.2239 (2)	0.073 (3)
O20	0.1108 (3)	1.0684 (2)	0.2873 (2)	0.059 (2)
C1	0.6220 (3)	0.6781 (3)	0.0958 (3)	0.038 (2)
C2	0.5864 (3)	0.5119 (3)	0.1685 (3)	0.038 (2)
C3	0.3915 (4)	0.5354 (3)	0.2496 (3)	0.041 (3)
C5	0.3130 (3)	0.8101 (3)	0.2583 (2)	0.034 (2)
C6	0.4699 (4)	0.8856 (3)	0.2317 (3)	0.039 (3)
C9	0.3069 (4)	0.7687 (3)	0.1299 (3)	0.038 (2)
C12	0.7197 (4)	0.4070 (3)	0.2422 (3)	0.045 (3)
C14	0.7688 (7)	0.4711 (5)	0.3378 (4)	0.074 (5)
C19	0.1414 (4)	0.8993 (3)	0.3428 (3)	0.044 (3)
C15	−0.0234 (5)	0.8336 (5)	0.3708 (4)	0.060 (4)
C16	0.7921 (5)	0.6598 (4)	−0.0066 (4)	0.054 (3)
C11	0.3367 (6)	0.3830 (4)	0.3272 (4)	0.057 (4)
C17	0.1737 (6)	0.8747 (4)	0.0571 (4)	0.056 (4)
C18	0.4963 (5)	0.9322 (4)	0.3460 (4)	0.052 (3)
H2	0.597 (3)	0.444 (2)	0.105 (2)	0.024 (6)*
H6	0.443 (3)	0.984 (3)	0.164 (3)	0.055 (8)*
H14	0.177 (3)	0.888 (3)	0.430 (2)	0.050 (8)*
H16	−0.008 (3)	1.102 (3)	0.285 (3)	0.058 (9)*
H121	0.831 (5)	0.385 (4)	0.395 (4)	0.141 (16)*
H122	0.83856	0.54257	0.29693	0.04723*
H123	0.656 (5)	0.507 (5)	0.391 (4)	0.16 (2)*
H151	−0.121 (4)	0.881 (3)	0.443 (3)	0.071 (10)*
H152	0.018 (4)	0.716 (4)	0.397 (3)	0.089 (12)*
H153	−0.078 (4)	0.838 (4)	0.301 (3)	0.099 (13)*
H171	0.902 (4)	0.630 (3)	0.035 (3)	0.103 (13)*
H172	0.809 (4)	0.581 (4)	−0.062 (3)	0.100 (13)*
H173	0.799 (4)	0.753 (4)	−0.065 (3)	0.124 (16)*
H181	0.364 (4)	0.315 (3)	0.264 (3)	0.079 (12)*
H182	0.207 (4)	0.406 (3)	0.378 (3)	0.068 (10)*
H183	0.414 (4)	0.338 (4)	0.392 (3)	0.093 (12)*
H191	0.190 (4)	0.826 (3)	−0.024 (3)	0.093 (12)*
H192	0.054 (5)	0.863 (4)	0.119 (4)	0.111 (15)*
H193	0.191 (4)	0.965 (3)	0.042 (3)	0.081 (13)*
H201	0.389 (3)	1.011 (3)	0.378 (2)	0.050 (8)*
H202	0.514 (3)	0.842 (3)	0.418 (3)	0.070 (10)*
H203	0.617 (3)	0.960 (3)	0.324 (2)	0.059 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O4	0.0466 (11)	0.0303 (9)	0.0363 (11)	−0.0027 (8)	−0.0143 (9)	0.0003 (8)
O7	0.0348 (10)	0.0397 (10)	0.0498 (12)	−0.0052 (8)	−0.0126 (9)	−0.0086 (9)
O8	0.0422 (11)	0.0375 (10)	0.0363 (11)	−0.0010 (8)	−0.0140 (9)	−0.0016 (8)
O10	0.0484 (12)	0.0349 (10)	0.0598 (14)	−0.0083 (9)	−0.0292 (10)	−0.0034 (9)
O13	0.0836 (17)	0.0424 (12)	0.095 (2)	0.0175 (11)	−0.0556 (15)	−0.0137 (12)
O20	0.0461 (13)	0.0358 (11)	0.0868 (18)	0.0025 (10)	−0.0215 (13)	−0.0007 (11)
C1	0.0345 (15)	0.0388 (14)	0.0385 (16)	−0.0020 (12)	−0.0094 (13)	−0.0077 (12)
C2	0.0383 (15)	0.0347 (13)	0.0384 (16)	−0.0015 (12)	−0.0164 (13)	−0.0032 (12)
C3	0.0479 (17)	0.0323 (13)	0.0443 (17)	−0.0057 (12)	−0.0215 (14)	0.0011 (12)
C5	0.0325 (15)	0.0312 (12)	0.0352 (15)	−0.0034 (11)	−0.0117 (12)	0.0005 (11)
C6	0.0313 (14)	0.0372 (14)	0.0462 (18)	−0.0015 (12)	−0.0144 (13)	−0.0057 (13)
C9	0.0419 (16)	0.0281 (13)	0.0436 (16)	−0.0036 (11)	−0.0208 (13)	0.0000 (11)
C12	0.0378 (16)	0.0432 (15)	0.0473 (18)	0.0018 (13)	−0.0159 (14)	−0.0039 (14)
C14	0.094 (3)	0.059 (2)	0.085 (3)	−0.004 (2)	−0.063 (3)	−0.008 (2)
C19	0.0362 (16)	0.0396 (15)	0.050 (2)	−0.0010 (12)	−0.0119 (15)	−0.0052 (14)
C15	0.038 (2)	0.064 (2)	0.073 (3)	−0.0135 (17)	−0.004 (2)	−0.012 (2)
C16	0.050 (2)	0.053 (2)	0.049 (2)	−0.0065 (16)	−0.0008 (17)	−0.0104 (17)
C11	0.065 (2)	0.0378 (17)	0.066 (3)	−0.0187 (16)	−0.017 (2)	0.0062 (17)
C17	0.060 (2)	0.048 (2)	0.062 (2)	0.0049 (18)	−0.038 (2)	−0.0081 (19)
C18	0.048 (2)	0.054 (2)	0.061 (2)	−0.0036 (16)	−0.0227 (18)	−0.0194 (18)

Geometric parameters (Å, º)

O4—C3	1.437 (4)	C9—C17	1.510 (5)
O4—C5	1.460 (3)	C12—C14	1.500 (7)
O7—C1	1.435 (4)	C14—H122	0.914 (5)
O7—C6	1.438 (3)	C14—H123	0.93 (4)
O8—C1	1.412 (3)	C14—H121	0.99 (4)
O8—C9	1.433 (3)	C19—H14	1.06 (3)
O10—C3	1.423 (4)	C19—C15	1.519 (5)
O10—C9	1.429 (3)	C15—H153	0.99 (4)
O13—C12	1.194 (3)	C15—H152	0.99 (3)
O20—H16	0.92 (3)	C15—H151	1.01 (3)
O20—C19	1.450 (3)	C16—H173	0.92 (3)
C1—C16	1.484 (4)	C16—H172	0.98 (4)
C1—C2	1.557 (4)	C16—H171	1.07 (4)
C2—H2	0.99 (2)	C11—H181	0.96 (3)
C2—C12	1.514 (4)	C11—H182	1.01 (3)
C2—C3	1.536 (4)	C11—H183	1.04 (4)
C3—C11	1.520 (4)	C17—H193	0.82 (3)
C5—C6	1.516 (4)	C17—H192	1.02 (3)
C5—C19	1.522 (3)	C17—H191	1.03 (4)
C5—C9	1.563 (4)	C18—H201	0.96 (2)
C6—H6	1.03 (2)	C18—H202	1.00 (3)
C6—C18	1.505 (6)	C18—H203	1.02 (3)
H172···H173	1.48 (5)	C2···H173	3.32 (3)
H121···H123	1.51 (5)	O13···H171	3.32 (3)
H202···H203	1.52 (4)	H151···H183	3.32 (4)
H152···H153	1.55 (5)	C12···H172	3.33 (3)
H192···H193	1.55 (5)	O13···C3	3.329 (3)
H121···H122	1.56 (3)	C1···H123	3.33 (4)
H191···H193	1.56 (5)	C3···C14	3.334 (7)
H201···H202	1.59 (3)	C11···H152	3.34 (3)
H122···H123	1.59 (4)	C15···C17	3.340 (6)
H171···H173	1.61 (5)	H193···H193	3.34 (5)
H151···H153	1.62 (5)	H182···H201	3.35 (3)
H151···H152	1.63 (4)	C17···H173	3.35 (4)
H182···H183	1.65 (4)	H201···H203	3.36 (4)
H181···H182	1.65 (4)	C14···H2	3.36 (3)
H181···H183	1.66 (5)	C6···H193	3.36 (4)
H191···H192	1.67 (5)	H171···H193	3.36 (4)
H171···H172	1.68 (6)	O8···H181	3.36 (3)
H201···H203	1.71 (3)	C15···H121	3.36 (4)
C12···H123	1.90 (5)	C15···H14	3.37 (3)
C9···H193	1.91 (3)	O13···C11	3.372 (5)
C19···H16	1.93 (2)	C17···H191	3.37 (3)
H153···H192	1.97 (5)	C11···H123	3.38 (5)
C3···H181	1.97 (3)	H183···H203	3.38 (4)
C12···H2	1.97 (2)	H123···H182	3.38 (6)
C9···H192	2.00 (4)	C11···H202	3.39 (3)
C6···H201	2.00 (3)	C16···H122	3.392 (4)
C12···H122	2.009 (4)	C19···H121	3.39 (4)
C19···H152	2.01 (3)	O4···H201	3.40 (3)
C5···H6	2.02 (2)	C16···H181	3.40 (4)
C1···H173	2.03 (3)	C15···H122	3.397 (5)
O7···H6	2.03 (2)	C11···H172	3.40 (4)
C3···H2	2.037 (18)	H6···H16	3.41 (3)
C5···H14	2.04 (2)	H202···H203	3.41 (4)
O20···H14	2.05 (2)	C17···C17	3.408 (6)
O13···H16	2.05 (2)	H121···H151	3.41 (5)
C3···H183	2.07 (3)	C5···H203	3.41 (3)
C9···H191	2.09 (4)	C17···H2	3.42 (2)
C6···H203	2.09 (3)	C18···H183	3.42 (3)
C1···H2	2.09 (2)	C3···C19	3.430 (4)
C1···H172	2.09 (3)	H6···H6	3.43 (4)
C1···H171	2.10 (3)	C5···H151	3.43 (3)
C12···H121	2.10 (5)	C19···H14	3.44 (2)
C19···H151	2.10 (3)	C18···H151	3.44 (3)
C18···H6	2.11 (3)	C2···H191	3.44 (3)
C3···H182	2.12 (3)	C14···H202	3.44 (3)
C15···H14	2.12 (3)	C11···H151	3.44 (3)
C6···H202	2.14 (3)	H2···H173	3.45 (4)
H14···H201	2.15 (4)	C18···H151	3.45 (3)
C19···H153	2.19 (4)	C3···H172	3.45 (4)
C3···C9	2.220 (3)	C2···H121	3.45 (4)
O4···O10	2.253 (3)	H151···H192	3.46 (5)
O7···O8	2.317 (3)	C2···H182	3.46 (3)
O13···H2	2.32 (2)	O4···C14	3.466 (5)
C3···C5	2.318 (4)	C9···H14	3.47 (3)
O8···O10	2.323 (2)	H16···H203	3.47 (4)
H6···H201	2.33 (4)	H172···H191	3.47 (4)
O13···C14	2.331 (6)	C14···H183	3.47 (3)
O10···C5	2.336 (4)	H16···H201	3.48 (4)
O8···C17	2.338 (4)	O4···H153	3.48 (3)
H153···H203	2.34 (4)	H16···H191	3.49 (5)
O7···C16	2.344 (4)	C11···H123	3.49 (5)
O4···C19	2.344 (3)	C16···H172	3.50 (3)
O13···C2	2.344 (3)	O20···C16	3.496 (4)
O7···C18	2.350 (4)	O10···C16	3.504 (5)
C15···H16	2.35 (2)	H121···H183	3.51 (5)
O8···C16	2.357 (4)	O13···C17	3.515 (6)
O4···C9	2.361 (3)	H16···H151	3.52 (5)
C1···C9	2.370 (4)	H121···H183	3.52 (6)
H14···H151	2.38 (4)	H172···H182	3.52 (5)
H14···H152	2.38 (5)	C5···H191	3.52 (4)
O10···C11	2.392 (4)	O10···C6	3.523 (4)
O20···C5	2.397 (3)	O7···H192	3.52 (4)
O10···C2	2.400 (3)	H2···H123	3.52 (6)
O10···C17	2.403 (4)	C6···H123	3.53 (4)
O4···C11	2.407 (4)	H2···H172	3.53 (4)
O8···C2	2.407 (3)	C16···H6	3.53 (2)
O4···H14	2.41 (2)	H171···H173	3.53 (4)
O4···C6	2.412 (3)	C6···C17	3.536 (6)
O7···C5	2.422 (3)	H152···H203	3.54 (4)
C1···C6	2.426 (4)	C18···H123	3.54 (4)
H183···H202	2.44 (4)	C18···H183	3.54 (3)
O4···C2	2.442 (3)	H151···H202	3.54 (3)
O8···C5	2.450 (3)	H192···H203	3.55 (4)
H2···H172	2.46 (3)	H172···H172	3.55 (5)
O7···H171	2.46 (3)	O13···C1	3.555 (3)
O7···H203	2.47 (3)	H202···H202	3.56 (5)
O20···C15	2.466 (5)	O10···H122	3.557 (2)
O8···H173	2.48 (3)	C15···H201	3.56 (2)
H16···H151	2.48 (4)	C17···H171	3.56 (4)
O7···C2	2.482 (4)	C14···H182	3.56 (3)
O13···H191	2.48 (4)	H173···H191	3.56 (6)
O8···H193	2.48 (3)	O13···H171	3.57 (3)
O10···H192	2.48 (3)	C9···C11	3.575 (4)
O13···H121	2.49 (5)	O20···H172	3.58 (3)
H16···H153	2.49 (5)	H191···H203	3.58 (4)
C6···C9	2.500 (5)	H14···H203	3.58 (4)
O4···H152	2.50 (3)	C6···C16	3.581 (4)
H2···H181	2.50 (3)	C18···H202	3.58 (3)
H171···H171	2.50 (4)	H6···H191	3.58 (4)
O8···H191	2.51 (3)	C16···H16	3.59 (2)
H6···H203	2.52 (4)	C15···H202	3.59 (3)
C2···C16	2.521 (4)	C3···C17	3.589 (5)
C1···C3	2.528 (4)	H151···H181	3.59 (4)
O8···H6	2.54 (3)	H153···H191	3.59 (4)
C6···C19	2.540 (4)	H182···H202	3.60 (4)
O10···H2	2.541 (17)	H183···H203	3.60 (4)
C3···C12	2.542 (4)	C14···H14	3.60 (2)
O10···H181	2.55 (3)	O13···H153	3.60 (3)
H173···H193	2.56 (5)	C5···C11	3.604 (4)
C5···C18	2.557 (6)	H122···H203	3.60 (2)
H151···H201	2.56 (3)	C12···H171	3.61 (3)
C18···H14	2.57 (2)	C14···H152	3.61 (4)
H171···H172	2.57 (4)	C15···H193	3.61 (3)
H14···H151	2.57 (4)	H122···H192	3.61 (3)
O8···C6	2.575 (4)	O4···O20	3.616 (2)
O10···H172	2.58 (4)	H201···H201	3.62 (4)
O20···H6	2.58 (2)	C14···H182	3.62 (3)
C9···H6	2.59 (3)	H122···H182	3.62 (3)
C2···C11	2.588 (5)	C18···H201	3.63 (3)
C5···C15	2.588 (4)	C11···H152	3.63 (3)
O7···H122	2.5935 (16)	O7···O10	3.635 (3)
O4···H123	2.60 (4)	H122···H183	3.64 (3)
H14···H202	2.60 (4)	C9···H16	3.64 (2)
O20···H201	2.61 (3)	C1···C17	3.639 (5)
O4···H183	2.61 (3)	H6···H173	3.64 (4)
H14···H16	2.61 (3)	O13···C16	3.644 (4)
C1···C12	2.618 (4)	C5···H123	3.65 (4)
C19···H201	2.62 (3)	C17···H6	3.65 (2)
O10···H191	2.62 (3)	C15···H182	3.66 (2)
O4···H182	2.62 (3)	O13···H172	3.66 (3)
O10···H182	2.62 (3)	C9···C16	3.661 (4)
O20···H173	2.63 (3)	C14···H153	3.66 (4)
C2···C14	2.625 (7)	C1···C18	3.663 (5)
C15···H192	2.64 (4)	C2···H2	3.66 (2)
H2···H191	2.65 (3)	O4···H122	3.667 (2)
O7···H173	2.65 (3)	C1···H6	3.67 (2)
C16···H2	2.65 (2)	O20···H182	3.67 (3)
C5···H152	2.65 (3)	C17···H152	3.68 (3)
H181···H201	2.66 (4)	C14···H152	3.68 (3)
C9···C19	2.658 (4)	C1···H193	3.68 (3)
O7···H202	2.66 (3)	C6···H181	3.68 (3)
O8···H2	2.662 (18)	C6···H122	3.680 (3)
H151···H203	2.67 (5)	O13···H172	3.68 (3)
C12···H183	2.67 (3)	O10···H171	3.68 (4)
C2···H181	2.67 (3)	C3···C15	3.687 (4)
C5···C17	2.674 (6)	C6···H193	3.69 (3)
C2···H123	2.68 (5)	C6···H16	3.70 (2)
C6···H14	2.69 (2)	O4···C17	3.706 (5)
C2···H172	2.70 (3)	C3···H192	3.71 (3)
C1···C5	2.706 (3)	C16···C16	3.711 (5)
H152···H182	2.72 (4)	C6···H173	3.71 (3)
C5···H201	2.72 (3)	C1···H2	3.71 (3)
O8···H172	2.72 (3)	O20···C12	3.724 (3)
H14···H121	2.72 (4)	O4···H192	3.72 (4)
O4···O7	2.738 (2)	C9···H172	3.73 (4)
O8···C3	2.746 (3)	C5···H182	3.73 (3)
C2···C9	2.746 (3)	C6···H173	3.74 (3)
H122···H171	2.76 (3)	O13···H151	3.74 (3)
H123···H183	2.77 (6)	C12···H172	3.74 (3)
C11···H2	2.773 (19)	O4···H151	3.74 (2)
O20···H151	2.77 (3)	C11···H203	3.74 (2)
H121···H152	2.78 (6)	C18···H122	3.743 (3)
C5···H193	2.79 (3)	C3···H14	3.75 (2)
H16···H173	2.79 (4)	O10···C12	3.755 (3)
H16···H121	2.79 (5)	C16···H6	3.75 (2)
H152···H182	2.80 (4)	C18···H203	3.76 (3)
C1···H6	2.80 (2)	C11···H121	3.76 (4)
C2···H183	2.80 (3)	C11···C18	3.757 (5)
C19···H6	2.81 (2)	C5···H2	3.77 (2)
H6···H173	2.81 (4)	C14···C16	3.775 (6)
O20···H153	2.81 (4)	O13···C16	3.775 (4)
H6···H193	2.82 (5)	O7···C19	3.777 (3)
O20···C6	2.828 (3)	C1···H193	3.78 (3)
C5···H192	2.83 (4)	C12···H173	3.79 (3)
H172···H181	2.84 (5)	O8···C12	3.800 (3)
O4···H202	2.84 (3)	C15···C18	3.801 (6)
O13···H123	2.84 (5)	C14···H123	3.80 (4)
C5···H202	2.85 (3)	O20···H202	3.81 (3)
H123···H183	2.85 (6)	C9···H182	3.81 (3)
O13···H122	2.854 (2)	O8···C19	3.809 (3)
O10···C1	2.857 (4)	C5···H121	3.81 (4)
C17···H153	2.86 (3)	C14···H172	3.81 (3)
O8···H6	2.86 (2)	O13···H192	3.82 (3)
H123···H202	2.87 (5)	C3···H122	3.820 (3)
H122···H153	2.87 (4)	C14···C11	3.823 (8)
O4···C1	2.876 (3)	O8···C6	3.824 (3)
O7···C9	2.878 (4)	C16···H191	3.83 (4)
C19···H192	2.88 (5)	O20···C14	3.829 (4)
C2···H171	2.88 (3)	C3···H123	3.83 (5)
O20···H193	2.88 (4)	C16···H192	3.83 (5)
O13···O20	2.888 (3)	C9···H6	3.83 (2)
O10···H152	2.90 (3)	C19···H173	3.84 (3)
O4···H121	2.91 (4)	C3···C16	3.843 (4)
C2···H122	2.914 (3)	O10···C2	3.843 (4)
O7···H123	2.92 (4)	C6···H153	3.84 (4)
H16···H192	2.93 (5)	O13···H14	3.85 (3)
H123···H123	2.93 (5)	O4···H203	3.86 (3)
H192···H193	2.93 (5)	C9···H181	3.86 (3)
C3···H123	2.94 (5)	O8···H193	3.86 (3)
H122···H152	2.94 (4)	O10···H173	3.86 (4)
O4···C15	2.947 (4)	O13···C15	3.866 (4)
H151···H182	2.95 (4)	C6···H171	3.87 (3)
O8···H2	2.95 (3)	C3···H2	3.87 (2)
C15···H203	2.95 (3)	C15···H183	3.88 (3)
O7···C14	2.955 (4)	C1···H191	3.88 (3)
H183···H201	2.97 (5)	O10···H6	3.88 (3)
O10···H2	2.97 (2)	C9···H173	3.88 (3)
C19···C18	2.972 (5)	C18···C18	3.879 (6)
H6···H202	2.97 (4)	O20···C11	3.880 (5)
C12···H16	2.97 (2)	O20···C15	3.883 (6)
C12···H171	2.98 (3)	C6···C14	3.886 (5)
C16···H171	2.98 (3)	C9···C18	3.894 (6)
O13···H183	2.99 (3)	O7···H14	3.89 (2)
C5···H153	2.99 (3)	C1···H203	3.89 (3)
C12···C11	2.999 (5)	O13···H193	3.90 (4)
H16···H193	3.00 (4)	O13···H193	3.90 (3)
H14···H153	3.01 (5)	C3···H153	3.90 (3)
H2···H2	3.02 (3)	O8···C2	3.903 (4)
H152···H192	3.03 (5)	C1···H202	3.91 (3)
C2···C5	3.026 (3)	C11···H121	3.91 (4)
H121···H182	3.04 (5)	O7···C17	3.916 (4)
O4···H123	3.04 (4)	C11···H173	3.92 (5)
H191···H192	3.04 (4)	O7···H121	3.92 (3)
H14···H16	3.04 (4)	C6···C15	3.928 (5)
O4···C18	3.050 (5)	C19···H16	3.93 (3)
O7···C12	3.059 (3)	C3···H121	3.93 (4)
C5···H16	3.06 (2)	C1···C11	3.929 (5)
O20···H192	3.07 (5)	C3···H191	3.93 (3)
C1···H122	3.068 (3)	O13···C19	3.933 (3)
C9···H153	3.07 (3)	C17···H172	3.94 (3)
O10···H193	3.08 (3)	C5···H173	3.94 (3)
H171···H192	3.09 (6)	C1···H181	3.94 (3)
O7···C3	3.097 (4)	C3···H6	3.94 (2)
H171···H191	3.10 (5)	O20···H171	3.95 (3)
C11···H201	3.11 (3)	C11···H122	3.947 (5)
C3···H152	3.11 (3)	C12···H182	3.95 (3)
C9···H2	3.119 (17)	C2···H6	3.95 (2)
O4···O8	3.120 (2)	O13···H192	3.95 (4)
C12···H181	3.13 (3)	O10···H14	3.96 (3)
H191···H193	3.13 (4)	C9···H173	3.96 (3)
H173···H181	3.13 (6)	C19···H203	3.96 (3)
O10···H153	3.13 (3)	C14···C11	3.963 (7)
H2···H183	3.13 (4)	C12···C16	3.971 (4)
O4···C12	3.134 (3)	O7···H191	3.98 (3)
H14···H14	3.14 (3)	C6···H192	3.99 (4)
C12···C16	3.142 (4)	C15···C11	3.996 (5)
H153···H202	3.14 (4)	C5···H183	4.00 (3)
O20···H151	3.15 (3)	C14···C18	4.003 (5)
H2···H171	3.15 (4)	C16···H122	4.004 (3)
C19···C17	3.149 (6)	C19···C19	4.005 (4)
H6···H181	3.15 (4)	C16···H2	4.01 (3)
H151···H202	3.16 (5)	C9···H172	4.01 (3)
O7···H201	3.16 (2)	O20···C19	4.017 (4)
C9···C15	3.167 (4)	O10···C1	4.018 (4)
O8···H192	3.17 (3)	C2···H171	4.03 (3)
C19···H193	3.17 (3)	O13···C18	4.049 (5)
H6···H14	3.18 (3)	C5···C12	4.057 (3)
O4···H181	3.18 (3)	O8···C18	4.062 (5)
H122···H182	3.19 (3)	O8···O10	4.065 (3)
C17···H192	3.19 (4)	C16···C17	4.066 (6)
C9···H152	3.20 (3)	C19···C15	4.080 (6)
C18···H153	3.20 (3)	C6···C12	4.081 (4)
O20···C18	3.202 (5)	C16···C11	4.114 (7)
H6···H193	3.21 (4)	C14···C15	4.122 (7)
O20···C17	3.209 (5)	O10···C16	4.122 (4)
C18···H181	3.21 (3)	O7···C17	4.135 (5)
C17···H6	3.22 (3)	C5···C16	4.144 (4)
H201···H202	3.22 (5)	O7···C15	4.152 (6)
H153···H193	3.22 (4)	O4···O13	4.158 (2)
O13···H181	3.22 (3)	C9···C12	4.161 (4)
C1···C14	3.223 (5)	O8···O20	4.161 (3)
O20···C9	3.224 (3)	C2···C17	4.161 (5)
O13···H203	3.22 (3)	O8···O8	4.178 (3)
O7···H193	3.22 (3)	O7···O13	4.186 (3)
O20···H121	3.23 (3)	C5···C14	4.193 (5)
O7···H172	3.23 (3)	C15···C11	4.194 (5)
O7···H153	3.24 (4)	O8···C11	4.199 (4)
C19···H202	3.24 (3)	O8···O13	4.210 (4)
C14···H183	3.24 (4)	C6···C17	4.219 (5)
H181···H203	3.24 (3)	C3···C18	4.224 (5)
O13···H173	3.24 (3)	C1···C19	4.224 (4)
O4···H6	3.25 (2)	O7···O20	4.227 (2)
O4···H2	3.25 (2)	O8···C11	4.227 (5)
C16···H193	3.25 (3)	O10···O20	4.229 (3)
C3···C6	3.257 (4)	O7···O8	4.244 (2)
O10···H183	3.26 (3)	O8···C3	4.268 (4)
O8···H171	3.26 (3)	O13···C17	4.273 (4)
O20···H152	3.27 (3)	C3···C16	4.282 (6)
O10···C15	3.273 (4)	C2···C9	4.290 (4)
O4···C14	3.274 (5)	C2···C17	4.301 (5)
C17···H193	3.27 (3)	C12···C17	4.303 (6)
O10···C19	3.275 (4)	C14···C19	4.314 (5)
C12···H191	3.29 (4)	O13···C9	4.316 (4)
H192···H192	3.29 (5)	O4···C16	4.324 (4)
C17···H16	3.29 (3)	C2···C18	4.331 (5)
C14···H16	3.29 (2)	C14···C15	4.332 (6)
O20···H181	3.30 (3)	C16···C17	4.335 (7)
H16···H152	3.30 (4)	C11···C18	4.345 (5)
O7···H2	3.30 (2)	C3···C14	4.348 (5)
C2···C6	3.304 (4)	C14···C16	4.354 (5)
C14···H171	3.31 (3)	C19···C11	4.357 (4)
C19···H151	3.31 (3)	O10···C14	4.358 (5)
C9···H2	3.31 (2)	O10···O13	4.373 (3)
O20···H14	3.31 (2)	C14···C11	4.390 (7)
H122···H202	3.31 (2)	C2···C2	4.431 (5)
H122···H172	3.32 (3)	C15···C18	4.435 (5)
C15···H182	3.32 (3)	C15···C18	4.439 (6)
H121···H182	3.32 (6)
C3—O4—C5	106.32 (19)	C14—C12—C2	121.2 (3)
C1—O7—C6	115.2 (2)	H122—C14—H123	119 (3)
C1—O8—C9	112.8 (2)	H122—C14—H121	109 (3)
C3—O10—C9	102.3 (2)	H122—C14—C12	110.4 (4)
H16—O20—C19	106.9 (15)	H123—C14—H121	104 (3)
O8—C1—O7	108.88 (18)	H123—C14—C12	101 (3)
O8—C1—C16	108.9 (2)	H121—C14—C12	113 (3)
O8—C1—C2	108.2 (2)	H14—C19—O20	107.9 (13)
O7—C1—C16	106.8 (3)	H14—C19—C15	109.2 (13)
O7—C1—C2	112.0 (2)	H14—C19—C5	102.7 (11)
C16—C1—C2	112.0 (2)	O20—C19—C15	112.3 (2)
H2—C2—C12	102.3 (11)	O20—C19—C5	107.5 (2)
H2—C2—C3	105.7 (12)	C15—C19—C5	116.6 (3)
H2—C2—C1	108.4 (11)	H153—C15—H152	103 (3)
C12—C2—C3	113.0 (2)	H153—C15—H151	108 (3)
C12—C2—C1	116.9 (3)	H153—C15—C19	120.1 (19)
C3—C2—C1	109.63 (19)	H152—C15—H151	109 (2)
O10—C3—O4	103.96 (18)	H152—C15—C19	105 (2)
O10—C3—C11	108.7 (3)	H151—C15—C19	111 (2)
O10—C3—C2	108.4 (2)	H173—C16—H172	102 (3)
O4—C3—C11	108.9 (2)	H173—C16—H171	107 (3)
O4—C3—C2	110.4 (3)	H173—C16—C1	112.4 (19)
C11—C3—C2	115.8 (2)	H172—C16—H171	110 (2)
O4—C5—C6	108.3 (2)	H172—C16—C1	114.8 (18)
O4—C5—C19	103.63 (18)	H171—C16—C1	109.5 (16)
O4—C5—C9	102.7 (2)	H181—C11—H182	114 (3)
C6—C5—C19	113.5 (2)	H181—C11—H183	113 (2)
C6—C5—C9	108.6 (2)	H181—C11—C3	103.3 (16)
C19—C5—C9	119.0 (2)	H182—C11—H183	107 (2)
H6—C6—O7	110.1 (12)	H182—C11—C3	112.0 (14)
H6—C6—C18	111.7 (17)	H183—C11—C3	106.8 (19)
H6—C6—C5	103.3 (16)	H193—C17—H192	115 (3)
O7—C6—C18	106.0 (2)	H193—C17—H191	114 (3)
O7—C6—C5	110.1 (2)	H193—C17—C9	106 (2)
C18—C6—C5	115.7 (2)	H192—C17—H191	109 (3)
O10—C9—O8	108.48 (18)	H192—C17—C9	103 (2)
O10—C9—C17	109.7 (3)	H191—C17—C9	108.9 (15)
O10—C9—C5	102.6 (2)	H201—C18—H202	108 (2)
O8—C9—C17	105.1 (2)	H201—C18—H203	120 (2)
O8—C9—C5	109.6 (2)	H201—C18—C6	106 (2)
C17—C9—C5	120.9 (2)	H202—C18—H203	98 (2)
O13—C12—C14	119.4 (3)	H202—C18—C6	115 (2)
O13—C12—C2	119.4 (3)	H203—C18—C6	110.6 (16)
C5—O4—C3—O10	−34.0 (2)	O10—C3—C11—H183	−174.8 (17)
C5—O4—C3—C2	82.1 (2)	C2—C3—C11—H181	−56.1 (19)
C5—O4—C3—C11	−149.7 (3)	C2—C3—C11—H182	−180 (2)
C3—O4—C5—C6	−107.1 (2)	C2—C3—C11—H183	63.1 (17)
C3—O4—C5—C9	7.7 (2)	O4—C5—C6—O7	51.3 (3)
C3—O4—C5—C19	132.1 (2)	O4—C5—C6—C18	−68.8 (3)
C6—O7—C1—O8	26.3 (3)	O4—C5—C6—H6	168.8 (15)
C6—O7—C1—C2	−93.3 (2)	C9—C5—C6—O7	−59.5 (3)
C6—O7—C1—C16	143.7 (2)	C9—C5—C6—C18	−179.6 (2)
C1—O7—C6—C5	35.9 (3)	C9—C5—C6—H6	58.0 (15)
C1—O7—C6—C18	161.7 (2)	C19—C5—C6—O7	165.8 (2)
C1—O7—C6—H6	−77.3 (19)	C19—C5—C6—C18	45.6 (3)
C9—O8—C1—O7	−70.1 (3)	C19—C5—C6—H6	−76.7 (15)
C9—O8—C1—C2	51.9 (3)	O4—C5—C9—O8	−94.4 (2)
C9—O8—C1—C16	173.8 (3)	O4—C5—C9—O10	20.7 (2)
C1—O8—C9—O10	−68.5 (3)	O4—C5—C9—C17	143.2 (3)
C1—O8—C9—C5	42.8 (3)	C6—C5—C9—O8	20.1 (2)
C1—O8—C9—C17	174.2 (3)	C6—C5—C9—O10	135.25 (19)
C9—O10—C3—O4	47.8 (2)	C6—C5—C9—C17	−102.3 (3)
C9—O10—C3—C2	−69.7 (2)	C19—C5—C9—O8	152.0 (2)
C9—O10—C3—C11	163.8 (2)	C19—C5—C9—O10	−92.9 (2)
C3—O10—C9—O8	74.4 (3)	C19—C5—C9—C17	29.5 (4)
C3—O10—C9—C5	−41.5 (2)	O4—C5—C19—O20	168.5 (2)
C3—O10—C9—C17	−171.3 (2)	O4—C5—C19—C15	−64.4 (3)
H16—O20—C19—C5	133 (2)	O4—C5—C19—H14	54.9 (14)
H16—O20—C19—C15	3 (2)	C6—C5—C19—O20	51.3 (3)
H16—O20—C19—H14	−117 (2)	C6—C5—C19—C15	178.3 (3)
O7—C1—C2—C3	73.5 (3)	C6—C5—C19—H14	−62.4 (14)
O7—C1—C2—C12	−56.7 (3)	C9—C5—C19—O20	−78.4 (3)
O7—C1—C2—H2	−171.6 (12)	C9—C5—C19—C15	48.7 (3)
O8—C1—C2—C3	−46.5 (3)	C9—C5—C19—H14	168.0 (14)
O8—C1—C2—C12	−176.7 (2)	O7—C6—C18—H201	176.7 (16)
O8—C1—C2—H2	68.4 (12)	O7—C6—C18—H202	−64.1 (16)
C16—C1—C2—C3	−166.5 (3)	O7—C6—C18—H203	45.8 (13)
C16—C1—C2—C12	63.3 (4)	C5—C6—C18—H201	−60.9 (16)
C16—C1—C2—H2	−51.6 (13)	C5—C6—C18—H202	58.3 (16)
O7—C1—C16—H171	45.9 (17)	C5—C6—C18—H203	168.2 (13)
O7—C1—C16—H172	170 (2)	H6—C6—C18—H201	57 (2)
O7—C1—C16—H173	−74 (3)	H6—C6—C18—H202	176 (2)
O8—C1—C16—H171	163.4 (17)	H6—C6—C18—H203	−74 (2)
O8—C1—C16—H172	−72 (2)	O8—C9—C17—H191	56.5 (18)
O8—C1—C16—H173	44 (3)	O8—C9—C17—H192	172 (2)
C2—C1—C16—H171	−77.1 (18)	O8—C9—C17—H193	−67 (2)
C2—C1—C16—H172	47 (2)	O10—C9—C17—H191	−59.9 (18)
C2—C1—C16—H173	164 (3)	O10—C9—C17—H192	55 (2)
C1—C2—C3—O4	−55.3 (3)	O10—C9—C17—H193	176 (2)
C1—C2—C3—O10	58.0 (3)	C5—C9—C17—H191	−178.9 (18)
C1—C2—C3—C11	−179.7 (3)	C5—C9—C17—H192	−64 (2)
C12—C2—C3—O4	77.1 (3)	C5—C9—C17—H193	57 (2)
C12—C2—C3—O10	−169.7 (2)	O13—C12—C14—H121	−15 (2)
C12—C2—C3—C11	−47.3 (4)	O13—C12—C14—H122	108.1 (4)
H2—C2—C3—O4	−171.9 (11)	O13—C12—C14—H123	−125 (2)
H2—C2—C3—O10	−58.7 (12)	C2—C12—C14—H121	165 (2)
H2—C2—C3—C11	63.7 (12)	C2—C12—C14—H122	−72.0 (4)
C1—C2—C12—O13	−127.3 (3)	C2—C12—C14—H123	55 (2)
C1—C2—C12—C14	52.7 (4)	O20—C19—C15—H151	−69.1 (17)
C3—C2—C12—O13	104.0 (3)	O20—C19—C15—H152	173 (2)
C3—C2—C12—C14	−75.9 (4)	O20—C19—C15—H153	59 (2)
H2—C2—C12—O13	−9.1 (12)	C5—C19—C15—H151	166.2 (17)
H2—C2—C12—C14	171.0 (12)	C5—C19—C15—H152	48 (2)
O4—C3—C11—H181	178.8 (18)	C5—C19—C15—H153	−66 (2)
O4—C3—C11—H182	55 (2)	H14—C19—C15—H151	50 (2)
O4—C3—C11—H183	−62.1 (17)	H14—C19—C15—H152	−67 (2)
O10—C3—C11—H181	66.1 (18)	H14—C19—C15—H153	178 (2)
O10—C3—C11—H182	−57 (2)