Tetra-methyl 1,4-dimethyl-13,14-dioxa-penta-cyclo-[8.2.1.1(4,7).0(2,9).0(3,8)]tetra-deca-5,11-diene-5,6,11,12-tetra-carboxyl-ate.

In the title compound, C(22)H(24)O(14), the relative stereochemistry at the cyclo-butane ring is cis-anti-cis and the methyl groups in the bicyclic rings are syn to each other. The two carboxyl-ate groups attached to the same -C=C- bond are disordered over two sets of sites in a 0.603 (2):0.397 (2) ratio. In the crystal, weak C-H⋯O hydrogen bonds connect mol-ecules into C(12) chains along [001] incorporating R(2) (2) (2)(10) rings.

Related literature

For related structures, see: Lough et al. (2012a ▶,b ▶). For the synthetic background, see: Ballantine et al. (2009 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C22H24O10

M = 448.41

Orthorhombic,

a = 11.5170 (14) Å

b = 13.9586 (15) Å

c = 26.413 (3) Å

V = 4246.1 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 147 K

0.33 × 0.22 × 0.06 mm

Data collection

Bruker Kappa APEX DUO CCD diffractometer

Absorption correction: multi-scan (Bruker, 2007 ▶) T min = 0.964, T max = 0.993

19411 measured reflections

4850 independent reflections

2974 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.096

S = 0.90

4850 reflections

322 parameters

32 restraints

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812039219/hb6952sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039219/hb6952Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812039219/hb6952Isup3.cml

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

C22H24O10	F(000) = 1888
Mr = 448.41	Dx = 1.403 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5611 reflections
a = 11.5170 (14) Å	θ = 2.4–27.4°
b = 13.9586 (15) Å	µ = 0.11 mm−1
c = 26.413 (3) Å	T = 147 K
V = 4246.1 (8) Å3	Plate, colourless
Z = 8	0.33 × 0.22 × 0.06 mm

Bruker Kappa APEX DUO CCD diffractometer	4850 independent reflections
Radiation source: fine-focus sealed tube	2974 reflections with I > 2σ(I)
Bruker Triumph monochromator	Rint = 0.055
φ and ω scans	θmax = 27.5°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −14→14
Tmin = 0.964, Tmax = 0.993	k = −10→18
19411 measured reflections	l = −34→18

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H-atom parameters constrained
S = 0.90	w = 1/[σ2(Fo2) + (0.0451P)2] where P = (Fo2 + 2Fc2)/3
4850 reflections	(Δ/σ)max = 0.001
322 parameters	Δρmax = 0.26 e Å−3
32 restraints	Δρmin = −0.20 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.81775 (11)	0.24086 (8)	−0.04639 (4)	0.0228 (3)
O2	0.87040 (10)	0.50450 (8)	0.06438 (4)	0.0202 (3)
O3	0.77858 (13)	0.36303 (10)	−0.19294 (4)	0.0398 (4)
O4	0.85192 (11)	0.49305 (9)	−0.15417 (4)	0.0263 (3)
O5	1.15910 (11)	0.28111 (9)	−0.10455 (4)	0.0268 (3)
O6	1.06300 (11)	0.35923 (9)	−0.16646 (4)	0.0269 (3)
O7	0.6189 (2)	0.3994 (2)	0.18885 (7)	0.0503 (7)	0.603 (2)
O8	0.5320 (9)	0.4330 (6)	0.1139 (5)	0.0327 (14)	0.603 (2)
O9	0.8653 (3)	0.3827 (2)	0.22013 (8)	0.0435 (8)	0.603 (2)
O10	0.9341 (6)	0.2732 (5)	0.1670 (5)	0.0290 (14)	0.603 (2)
C17	0.6234 (3)	0.4210 (2)	0.14455 (12)	0.0264 (8)	0.603 (2)
C19	0.8778 (3)	0.3546 (3)	0.17727 (10)	0.0249 (6)	0.603 (2)
C18	0.4202 (12)	0.4196 (9)	0.1391 (6)	0.0454 (6)	0.603 (2)
H18A	0.3578	0.4217	0.1139	0.068*	0.603 (2)
H18B	0.4085	0.4706	0.1640	0.068*	0.603 (2)
H18C	0.4193	0.3573	0.1562	0.068*	0.603 (2)
C20	0.9776 (10)	0.2224 (9)	0.2114 (6)	0.0436 (9)	0.603 (2)
H20A	1.0204	0.1653	0.2006	0.065*	0.603 (2)
H20B	0.9123	0.2033	0.2329	0.065*	0.603 (2)
H20C	1.0295	0.2646	0.2306	0.065*	0.603 (2)
O7A	0.6002 (3)	0.4831 (3)	0.18225 (12)	0.0503 (7)	0.397 (2)
O8A	0.5296 (14)	0.4105 (11)	0.1152 (8)	0.0327 (14)	0.397 (2)
O9A	0.7972 (4)	0.3518 (3)	0.21445 (14)	0.0435 (8)	0.397 (2)
O10A	0.9507 (10)	0.2917 (9)	0.1692 (8)	0.0290 (14)	0.397 (2)
C17A	0.6182 (4)	0.4469 (4)	0.14155 (16)	0.0264 (8)	0.397 (2)
C19A	0.8570 (5)	0.3462 (4)	0.17719 (13)	0.0249 (6)	0.397 (2)
C18A	0.4166 (19)	0.4198 (14)	0.1398 (10)	0.0454 (6)	0.397 (2)
H18D	0.3558	0.3959	0.1171	0.068*	0.397 (2)
H18E	0.4020	0.4873	0.1477	0.068*	0.397 (2)
H18F	0.4163	0.3823	0.1712	0.068*	0.397 (2)
C20A	0.9845 (17)	0.2309 (13)	0.2116 (8)	0.0436 (9)	0.397 (2)
H20D	1.0628	0.2059	0.2058	0.065*	0.397 (2)
H20E	0.9297	0.1775	0.2146	0.065*	0.397 (2)
H20F	0.9836	0.2686	0.2429	0.065*	0.397 (2)
C1	0.85556 (16)	0.34792 (12)	−0.11010 (5)	0.0196 (4)
C2	0.77038 (16)	0.32925 (12)	−0.06633 (5)	0.0200 (4)
C3	0.80888 (15)	0.40228 (12)	−0.02535 (5)	0.0170 (4)
H3A	0.8102	0.4708	−0.0364	0.020*
C4	0.75885 (15)	0.38416 (12)	0.02843 (5)	0.0172 (4)
H4A	0.6914	0.3392	0.0302	0.021*
C5	0.74926 (15)	0.47494 (12)	0.06159 (5)	0.0190 (4)
C6	0.73289 (15)	0.43738 (12)	0.11604 (5)	0.0200 (4)
C7	0.83590 (16)	0.40288 (12)	0.13030 (5)	0.0201 (4)
C8	0.91584 (16)	0.41679 (12)	0.08511 (5)	0.0190 (4)
H8A	1.0007	0.4176	0.0931	0.023*
C9	0.87811 (15)	0.34188 (12)	0.04533 (5)	0.0175 (4)
H9A	0.8773	0.2737	0.0569	0.021*
C10	0.92895 (15)	0.36020 (12)	−0.00825 (5)	0.0173 (4)
H10A	0.9962	0.4054	−0.0098	0.021*
C11	0.93701 (15)	0.27200 (12)	−0.04294 (5)	0.0204 (4)
H11A	0.9934	0.2218	−0.0318	0.024*
C12	0.95736 (16)	0.31197 (12)	−0.09594 (5)	0.0198 (4)
C13	0.82498 (16)	0.40042 (13)	−0.15740 (5)	0.0221 (4)
C14	0.83509 (19)	0.54896 (15)	−0.20023 (6)	0.0398 (5)
H14A	0.8350	0.6174	−0.1919	0.060*
H14B	0.7607	0.5317	−0.2157	0.060*
H14C	0.8983	0.5354	−0.2240	0.060*
C15	1.07098 (16)	0.31541 (12)	−0.12149 (5)	0.0194 (4)
C16	1.16955 (17)	0.36413 (15)	−0.19566 (6)	0.0331 (5)
H16A	1.1593	0.4087	−0.2240	0.050*
H16B	1.1885	0.3004	−0.2088	0.050*
H16C	1.2329	0.3867	−0.1739	0.050*
C21	0.64336 (16)	0.31957 (14)	−0.07817 (6)	0.0292 (5)
H21A	0.6325	0.2705	−0.1043	0.044*
H21B	0.6134	0.3810	−0.0905	0.044*
H21C	0.6013	0.3009	−0.0475	0.044*
C22	0.67345 (17)	0.55607 (13)	0.04345 (6)	0.0271 (4)
H22A	0.6715	0.6066	0.0692	0.041*
H22B	0.5946	0.5323	0.0375	0.041*
H22C	0.7051	0.5821	0.0119	0.041*

	U11	U22	U33	U12	U13	U23
O1	0.0276 (8)	0.0218 (7)	0.0189 (5)	−0.0031 (6)	0.0024 (5)	0.0019 (5)
O2	0.0201 (7)	0.0184 (6)	0.0221 (5)	−0.0020 (5)	0.0006 (5)	0.0023 (5)
O3	0.0495 (10)	0.0499 (9)	0.0200 (6)	−0.0059 (8)	−0.0140 (6)	−0.0024 (6)
O4	0.0292 (8)	0.0311 (8)	0.0185 (5)	−0.0006 (6)	−0.0042 (5)	0.0084 (5)
O5	0.0239 (8)	0.0290 (7)	0.0275 (6)	0.0066 (6)	−0.0018 (5)	−0.0016 (5)
O6	0.0217 (7)	0.0445 (8)	0.0145 (5)	0.0040 (6)	0.0054 (5)	0.0052 (5)
O7	0.0397 (13)	0.0895 (19)	0.0218 (9)	−0.0210 (16)	0.0109 (8)	−0.0115 (13)
O8	0.0193 (9)	0.037 (4)	0.0422 (9)	0.005 (2)	0.0050 (8)	0.001 (3)
O9	0.059 (2)	0.0560 (19)	0.0152 (8)	0.0237 (16)	0.0032 (13)	0.0002 (10)
O10	0.027 (2)	0.037 (3)	0.0225 (12)	0.007 (2)	−0.0007 (18)	0.009 (2)
C17	0.0282 (13)	0.029 (2)	0.0216 (10)	−0.0092 (13)	0.0044 (9)	−0.0074 (11)
C19	0.0325 (18)	0.0246 (12)	0.0175 (8)	−0.0020 (12)	0.0043 (9)	0.0009 (8)
C18	0.0207 (14)	0.0459 (14)	0.0696 (15)	0.0047 (11)	0.0146 (12)	−0.0102 (12)
C20	0.0403 (17)	0.055 (2)	0.0354 (10)	0.0094 (18)	−0.0040 (12)	0.0208 (13)
O7A	0.0397 (13)	0.0895 (19)	0.0218 (9)	−0.0210 (16)	0.0109 (8)	−0.0115 (13)
O8A	0.0193 (9)	0.037 (4)	0.0422 (9)	0.005 (2)	0.0050 (8)	0.001 (3)
O9A	0.059 (2)	0.0560 (19)	0.0152 (8)	0.0237 (16)	0.0032 (13)	0.0002 (10)
O10A	0.027 (2)	0.037 (3)	0.0225 (12)	0.007 (2)	−0.0007 (18)	0.009 (2)
C17A	0.0282 (13)	0.029 (2)	0.0216 (10)	−0.0092 (13)	0.0044 (9)	−0.0074 (11)
C19A	0.0325 (18)	0.0246 (12)	0.0175 (8)	−0.0020 (12)	0.0043 (9)	0.0009 (8)
C18A	0.0207 (14)	0.0459 (14)	0.0696 (15)	0.0047 (11)	0.0146 (12)	−0.0102 (12)
C20A	0.0403 (17)	0.055 (2)	0.0354 (10)	0.0094 (18)	−0.0040 (12)	0.0208 (13)
C1	0.0212 (10)	0.0244 (10)	0.0131 (7)	−0.0023 (8)	0.0007 (7)	−0.0009 (7)
C2	0.0200 (10)	0.0245 (10)	0.0154 (7)	−0.0012 (8)	0.0022 (7)	0.0018 (7)
C3	0.0158 (9)	0.0204 (9)	0.0149 (7)	−0.0001 (7)	0.0007 (6)	0.0033 (7)
C4	0.0166 (9)	0.0206 (9)	0.0144 (7)	−0.0027 (8)	0.0015 (6)	0.0000 (6)
C5	0.0169 (9)	0.0218 (9)	0.0182 (7)	−0.0023 (8)	0.0009 (7)	0.0004 (7)
C6	0.0243 (10)	0.0210 (9)	0.0148 (7)	−0.0039 (8)	0.0026 (7)	−0.0051 (7)
C7	0.0263 (11)	0.0189 (9)	0.0149 (7)	−0.0030 (8)	0.0012 (7)	−0.0037 (7)
C8	0.0197 (10)	0.0216 (10)	0.0158 (7)	0.0011 (8)	−0.0012 (7)	0.0030 (7)
C9	0.0207 (10)	0.0189 (9)	0.0128 (7)	−0.0001 (7)	0.0017 (6)	0.0021 (6)
C10	0.0170 (9)	0.0205 (9)	0.0144 (7)	0.0004 (8)	0.0014 (6)	0.0033 (7)
C11	0.0201 (10)	0.0244 (10)	0.0167 (7)	0.0027 (8)	0.0017 (7)	0.0025 (7)
C12	0.0235 (10)	0.0230 (10)	0.0127 (7)	0.0005 (8)	0.0016 (7)	−0.0008 (7)
C13	0.0187 (10)	0.0326 (11)	0.0149 (7)	0.0027 (8)	0.0032 (7)	0.0003 (7)
C14	0.0407 (14)	0.0500 (14)	0.0286 (9)	0.0003 (11)	−0.0041 (9)	0.0220 (9)
C15	0.0226 (11)	0.0201 (9)	0.0156 (7)	0.0021 (8)	−0.0001 (7)	−0.0042 (7)
C16	0.0278 (12)	0.0469 (13)	0.0245 (8)	−0.0030 (10)	0.0118 (8)	−0.0023 (8)
C21	0.0227 (11)	0.0459 (13)	0.0191 (8)	−0.0075 (10)	0.0002 (7)	−0.0012 (8)
C22	0.0269 (11)	0.0277 (11)	0.0266 (8)	0.0062 (9)	0.0004 (8)	0.0005 (8)

O1—C11	1.443 (2)	C20A—H20F	0.9800
O1—C2	1.448 (2)	C1—C12	1.329 (2)
O2—C8	1.4396 (19)	C1—C13	1.490 (2)
O2—C5	1.457 (2)	C1—C2	1.539 (2)
O3—C13	1.200 (2)	C2—C21	1.502 (3)
O4—C13	1.332 (2)	C2—C3	1.552 (2)
O4—C14	1.4584 (19)	C3—C4	1.554 (2)
O5—C15	1.208 (2)	C3—C10	1.569 (2)
O6—C15	1.3393 (19)	C3—H3A	1.0000
O6—C16	1.451 (2)	C4—C5	1.544 (2)
O7—C17	1.210 (3)	C4—C9	1.560 (2)
O8—C17	1.338 (3)	C4—H4A	1.0000
O8—C18	1.461 (3)	C5—C22	1.508 (2)
O9—C19	1.207 (3)	C5—C6	1.542 (2)
O10—C19	1.337 (3)	C6—C7	1.335 (2)
O10—C20	1.458 (3)	C7—C8	1.520 (2)
C17—C6	1.486 (3)	C8—C9	1.545 (2)
C19—C7	1.492 (3)	C8—H8A	1.0000
C18—H18A	0.9800	C9—C10	1.553 (2)
C18—H18B	0.9800	C9—H9A	1.0000
C18—H18C	0.9800	C10—C11	1.537 (2)
C20—H20A	0.9800	C10—H10A	1.0000
C20—H20B	0.9800	C11—C12	1.525 (2)
C20—H20C	0.9800	C11—H11A	1.0000
O7A—C17A	1.206 (4)	C12—C15	1.473 (2)
O8A—C17A	1.337 (4)	C14—H14A	0.9800
O8A—C18A	1.460 (4)	C14—H14B	0.9800
O9A—C19A	1.203 (4)	C14—H14C	0.9800
O10A—C19A	1.337 (4)	C16—H16A	0.9800
O10A—C20A	1.459 (4)	C16—H16B	0.9800
C17A—C6	1.488 (4)	C16—H16C	0.9800
C19A—C7	1.490 (4)	C21—H21A	0.9800
C18A—H18D	0.9800	C21—H21B	0.9800
C18A—H18E	0.9800	C21—H21C	0.9800
C18A—H18F	0.9800	C22—H22A	0.9800
C20A—H20D	0.9800	C22—H22B	0.9800
C20A—H20E	0.9800	C22—H22C	0.9800
C11—O1—C2	97.18 (12)	C17A—C6—C5	120.0 (2)
C8—O2—C5	97.27 (12)	C6—C7—C19A	124.8 (3)
C13—O4—C14	115.79 (13)	C6—C7—C19	133.23 (19)
C15—O6—C16	115.78 (14)	C6—C7—C8	105.71 (12)
C17—O8—C18	113.7 (10)	C19A—C7—C8	128.5 (3)
C19—O10—C20	114.7 (8)	C19—C7—C8	121.00 (19)
O7—C17—O8	125.6 (7)	O2—C8—C7	100.78 (13)
O7—C17—C6	124.4 (3)	O2—C8—C9	102.40 (12)
O8—C17—C6	110.0 (7)	C7—C8—C9	106.10 (13)
O9—C19—O10	121.6 (6)	O2—C8—H8A	115.3
O9—C19—C7	126.5 (3)	C7—C8—H8A	115.3
O10—C19—C7	111.9 (6)	C9—C8—H8A	115.3
C17A—O8A—C18A	114.4 (17)	C8—C9—C10	113.73 (13)
C19A—O10A—C20A	115.1 (14)	C8—C9—C4	100.73 (13)
O7A—C17A—O8A	119.5 (12)	C10—C9—C4	90.51 (11)
O7A—C17A—C6	126.5 (5)	C8—C9—H9A	116.0
O8A—C17A—C6	114.0 (11)	C10—C9—H9A	116.0
O9A—C19A—O10A	128.9 (10)	C4—C9—H9A	116.0
O9A—C19A—C7	123.5 (5)	C11—C10—C9	115.72 (13)
O10A—C19A—C7	107.6 (10)	C11—C10—C3	100.46 (13)
O8A—C18A—H18D	109.5	C9—C10—C3	89.52 (12)
O8A—C18A—H18E	109.5	C11—C10—H10A	115.7
H18D—C18A—H18E	109.5	C9—C10—H10A	115.7
O8A—C18A—H18F	109.5	C3—C10—H10A	115.7
H18D—C18A—H18F	109.5	O1—C11—C12	101.45 (12)
H18E—C18A—H18F	109.5	O1—C11—C10	102.78 (13)
O10A—C20A—H20D	109.5	C12—C11—C10	105.27 (13)
O10A—C20A—H20E	109.5	O1—C11—H11A	115.2
H20D—C20A—H20E	109.5	C12—C11—H11A	115.2
O10A—C20A—H20F	109.5	C10—C11—H11A	115.2
H20D—C20A—H20F	109.5	C1—C12—C15	129.97 (14)
H20E—C20A—H20F	109.5	C1—C12—C11	105.13 (14)
C12—C1—C13	129.05 (15)	C15—C12—C11	124.67 (15)
C12—C1—C2	106.68 (13)	O3—C13—O4	125.16 (15)
C13—C1—C2	124.23 (15)	O3—C13—C1	123.18 (17)
O1—C2—C21	111.47 (14)	O4—C13—C1	111.62 (14)
O1—C2—C1	100.22 (13)	O4—C14—H14A	109.5
C21—C2—C1	118.67 (13)	O4—C14—H14B	109.5
O1—C2—C3	101.44 (12)	H14A—C14—H14B	109.5
C21—C2—C3	118.86 (15)	O4—C14—H14C	109.5
C1—C2—C3	103.33 (13)	H14A—C14—H14C	109.5
C2—C3—C4	115.13 (14)	H14B—C14—H14C	109.5
C2—C3—C10	101.93 (13)	O5—C15—O6	124.55 (16)
C4—C3—C10	90.16 (11)	O5—C15—C12	124.31 (15)
C2—C3—H3A	115.4	O6—C15—C12	111.12 (15)
C4—C3—H3A	115.4	O6—C16—H16A	109.5
C10—C3—H3A	115.4	O6—C16—H16B	109.5
C5—C4—C3	114.29 (13)	H16A—C16—H16B	109.5
C5—C4—C9	102.18 (13)	O6—C16—H16C	109.5
C3—C4—C9	89.81 (12)	H16A—C16—H16C	109.5
C5—C4—H4A	115.7	H16B—C16—H16C	109.5
C3—C4—H4A	115.7	C2—C21—H21A	109.5
C9—C4—H4A	115.7	C2—C21—H21B	109.5
O2—C5—C22	110.97 (14)	H21A—C21—H21B	109.5
O2—C5—C6	99.57 (12)	C2—C21—H21C	109.5
C22—C5—C6	118.73 (14)	H21A—C21—H21C	109.5
O2—C5—C4	101.11 (13)	H21B—C21—H21C	109.5
C22—C5—C4	118.51 (13)	C5—C22—H22A	109.5
C6—C5—C4	104.99 (13)	C5—C22—H22B	109.5
C7—C6—C17	123.8 (2)	H22A—C22—H22B	109.5
C7—C6—C17A	133.9 (2)	C5—C22—H22C	109.5
C7—C6—C5	106.09 (14)	H22A—C22—H22C	109.5
C17—C6—C5	128.9 (2)	H22B—C22—H22C	109.5
C18—O8—C17—O7	1.3 (6)	C17A—C6—C7—C8	−179.3 (3)
C18—O8—C17—C6	−179.2 (4)	C5—C6—C7—C8	−0.99 (17)
C20—O10—C19—O9	0.2 (4)	O9A—C19A—C7—C6	−25.8 (5)
C20—O10—C19—C7	179.9 (2)	O10A—C19A—C7—C6	154.4 (5)
C18A—O8A—C17A—O7A	0.3 (6)	O9A—C19A—C7—C19	121 (2)
C18A—O8A—C17A—C6	−179.8 (4)	O10A—C19A—C7—C19	−59 (2)
C20A—O10A—C19A—O9A	0.1 (4)	O9A—C19A—C7—C8	167.3 (4)
C20A—O10A—C19A—C7	179.9 (2)	O10A—C19A—C7—C8	−12.5 (4)
C11—O1—C2—C21	176.12 (12)	O9—C19—C7—C6	−51.3 (4)
C11—O1—C2—C1	49.62 (12)	O10—C19—C7—C6	129.0 (4)
C11—O1—C2—C3	−56.37 (13)	O9—C19—C7—C19A	−89 (2)
C12—C1—C2—O1	−31.08 (16)	O10—C19—C7—C19A	91.3 (19)
C13—C1—C2—O1	151.18 (16)	O9—C19—C7—C8	132.0 (3)
C12—C1—C2—C21	−152.58 (16)	O10—C19—C7—C8	−47.6 (3)
C13—C1—C2—C21	29.7 (2)	C5—O2—C8—C7	−51.98 (13)
C12—C1—C2—C3	73.39 (17)	C5—O2—C8—C9	57.35 (13)
C13—C1—C2—C3	−104.35 (18)	C6—C7—C8—O2	33.57 (16)
O1—C2—C3—C4	−62.06 (17)	C19A—C7—C8—O2	−157.5 (3)
C21—C2—C3—C4	60.5 (2)	C19—C7—C8—O2	−148.9 (2)
C1—C2—C3—C4	−165.59 (14)	C6—C7—C8—C9	−72.84 (16)
O1—C2—C3—C10	33.81 (14)	C19A—C7—C8—C9	96.0 (3)
C21—C2—C3—C10	156.36 (14)	C19—C7—C8—C9	104.6 (2)
C1—C2—C3—C10	−69.72 (15)	O2—C8—C9—C10	60.81 (17)
C2—C3—C4—C5	−153.67 (15)	C7—C8—C9—C10	166.05 (13)
C10—C3—C4—C5	103.05 (15)	O2—C8—C9—C4	−34.53 (14)
C2—C3—C4—C9	103.03 (15)	C7—C8—C9—C4	70.71 (14)
C10—C3—C4—C9	−0.25 (12)	C5—C4—C9—C8	−0.31 (14)
C8—O2—C5—C22	176.56 (12)	C3—C4—C9—C8	114.53 (12)
C8—O2—C5—C6	50.64 (13)	C5—C4—C9—C10	−114.60 (12)
C8—O2—C5—C4	−56.84 (12)	C3—C4—C9—C10	0.25 (12)
C3—C4—C5—O2	−60.95 (16)	C8—C9—C10—C11	156.40 (14)
C9—C4—C5—O2	34.43 (13)	C4—C9—C10—C11	−101.64 (15)
C3—C4—C5—C22	60.5 (2)	C8—C9—C10—C3	−102.21 (15)
C9—C4—C5—C22	155.88 (15)	C4—C9—C10—C3	−0.25 (12)
C3—C4—C5—C6	−164.12 (14)	C2—C3—C10—C11	0.57 (14)
C9—C4—C5—C6	−68.74 (15)	C4—C3—C10—C11	116.34 (12)
O7—C17—C6—C7	21.3 (4)	C2—C3—C10—C9	−115.52 (12)
O8—C17—C6—C7	−158.1 (4)	C4—C3—C10—C9	0.25 (12)
O7—C17—C6—C17A	−116.9 (14)	C2—O1—C11—C12	−50.97 (13)
O8—C17—C6—C17A	63.7 (13)	C2—O1—C11—C10	57.78 (12)
O7—C17—C6—C5	−173.1 (2)	C9—C10—C11—O1	59.43 (16)
O8—C17—C6—C5	7.5 (3)	C3—C10—C11—O1	−35.13 (14)
O7A—C17A—C6—C7	51.7 (6)	C9—C10—C11—C12	165.26 (14)
O8A—C17A—C6—C7	−128.1 (6)	C3—C10—C11—C12	70.70 (15)
O7A—C17A—C6—C17	101.9 (14)	C13—C1—C12—C15	2.2 (3)
O8A—C17A—C6—C17	−77.9 (14)	C2—C1—C12—C15	−175.43 (17)
O7A—C17A—C6—C5	−126.4 (4)	C13—C1—C12—C11	176.74 (17)
O8A—C17A—C6—C5	53.8 (5)	C2—C1—C12—C11	−0.86 (18)
O2—C5—C6—C7	−31.31 (16)	O1—C11—C12—C1	32.81 (17)
C22—C5—C6—C7	−151.73 (16)	C10—C11—C12—C1	−74.00 (17)
C4—C5—C6—C7	73.01 (17)	O1—C11—C12—C15	−152.24 (15)
O2—C5—C6—C17	161.13 (19)	C10—C11—C12—C15	100.94 (18)
C22—C5—C6—C17	40.7 (3)	C14—O4—C13—O3	−7.5 (3)
C4—C5—C6—C17	−94.5 (2)	C14—O4—C13—C1	174.64 (15)
O2—C5—C6—C17A	147.2 (3)	C12—C1—C13—O3	99.2 (2)
C22—C5—C6—C17A	26.8 (3)	C2—C1—C13—O3	−83.6 (2)
C4—C5—C6—C17A	−108.4 (3)	C12—C1—C13—O4	−82.9 (2)
C17—C6—C7—C19A	−2.0 (3)	C2—C1—C13—O4	94.3 (2)
C17A—C6—C7—C19A	11.3 (5)	C16—O6—C15—O5	0.1 (2)
C5—C6—C7—C19A	−170.4 (3)	C16—O6—C15—C12	−178.24 (14)
C17—C6—C7—C19	−9.7 (4)	C1—C12—C15—O5	178.80 (18)
C17A—C6—C7—C19	3.7 (5)	C11—C12—C15—O5	5.2 (3)
C5—C6—C7—C19	−178.0 (3)	C1—C12—C15—O6	−2.9 (3)
C17—C6—C7—C8	167.37 (18)	C11—C12—C15—O6	−176.48 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O2i	1.00	2.45	3.332 (2)	146
C14—H14C···O7ii	0.98	2.48	3.063 (3)	118

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯O2i	1.00	2.45	3.332 (2)	146
C14—H14C⋯O7ii	0.98	2.48	3.063 (3)	118

Symmetry codes: (i) ; (ii) .