7-Oxogedunin

The title compound, 1-(3-furyl)-4b,7,7,10a,12a-penta­methyl-1,6a,7,10a,10b,11,12,12a-octa­hydro­naphtho­[2,1-f]­oxireno­[2,3-d]­isochromene-3,5,8(3aH,4bH,6H)-trione, C₂₆H₃₀O₆, has been isolated from Xyl­ocarpus granatum Koenig. All four rings are trans-fused. The four six-membered rings adopt distorted sofa, chair, twist-boat and half-chair conformations. The furan substituent is planar and attached equatorially to the lactone ring of the gedunin skeleton. The crystal structure is stabilized by C—H...O intramolecular and intermolecular interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.047
• wR factor = 0.110
• Data-to-parameter ratio = 7.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.93
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.00
           From the CIF: _reflns_number_total               2330
           Count of symmetry unique reflns         2335
           Completeness (_total/calc)             99.79%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present           no

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

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

---

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

1-(3-furyl)-4 b,7,7,10a,12a-pentamethyl-1,6a,7,10a,10b,11,12,12a- octahydronaphtho[2,1-f]oxireno[2,3-d]isochromene-3,5,8(3aH,4bH,6H)-trione

Crystal data

C26H30O6	Dx = 1.301 Mg m^−3
Mr = 438.50	Melting point = 533–535 K
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 7.6623 (12) Å	Cell parameters from 3780 reflections
b = 11.1298 (18) Å	θ = 1.6–28.3°
c = 13.350 (2) Å	µ = 0.09 mm^−1
β = 100.547 (3)°	T = 293 K
V = 1119.2 (3) Å^3	Plate, colorless
Z = 2	0.25 × 0.19 × 0.08 mm
F(000) = 468

Data collection

Siemens SMART CCD area detector diffractometer	2330 independent reflections
Radiation source: fine-focus sealed tube	2052 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
Detector resolution: 8.33 pixels mm^-1	θmax = 26.0°, θmin = 1.6°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −13→13
Tmin = 0.977, Tmax = 0.993	l = −16→16
8802 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.110	H-atom parameters constrained
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0538P)^2 + 0.1209P] where P = (Fo^2 + 2Fc^2)/3
2330 reflections	(Δ/σ)max < 0.001
294 parameters	Δρmax = 0.19 e Å^−3
1 restraint	Δρmin = −0.22 e Å^−3

Special details

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

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

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

	x	y	z	Uiso*/Ueq
O1	0.1781 (4)	0.1681 (3)	1.0009 (2)	0.0918 (11)
O2	0.5747 (3)	0.4522 (3)	0.64031 (19)	0.0640 (8)
O5	0.5713 (3)	0.6475 (3)	0.36168 (19)	0.0621 (7)
O3	0.2527 (3)	0.7087 (2)	0.51167 (18)	0.0485 (6)
O4	0.2930 (3)	0.5894 (2)	0.32426 (17)	0.0486 (6)
O6	−0.2004 (4)	0.4147 (3)	0.1606 (2)	0.0780 (10)
C1	0.1490 (4)	0.4382 (3)	0.7851 (2)	0.0336 (7)
C2	0.0036 (4)	0.3460 (3)	0.7886 (2)	0.0418 (8)
H2A	−0.1019	0.3527	0.7418	0.050*
C3	0.0204 (5)	0.2571 (3)	0.8548 (3)	0.0484 (9)
H3A	−0.0748	0.2048	0.8532	0.058*
C4	0.1809 (5)	0.2364 (3)	0.9307 (3)	0.0538 (9)
C5	0.3512 (5)	0.3044 (3)	0.9224 (2)	0.0460 (8)
C6	0.3259 (4)	0.3696 (3)	0.8180 (2)	0.0371 (7)
H6A	0.3199	0.3042	0.7683	0.045*
C7	0.4893 (4)	0.4431 (4)	0.8028 (3)	0.0528 (9)
H7A	0.5012	0.5131	0.8468	0.063*
H7B	0.5955	0.3947	0.8211	0.063*
C8	0.4699 (4)	0.4825 (4)	0.6933 (3)	0.0454 (9)
C9	0.3050 (4)	0.5563 (3)	0.6543 (2)	0.0359 (7)
C10	0.1448 (3)	0.4753 (3)	0.6729 (2)	0.0308 (6)
H10A	0.1614	0.3996	0.6383	0.037*
C11	−0.0236 (4)	0.5286 (3)	0.6100 (2)	0.0444 (8)
H11A	−0.0237	0.6152	0.6184	0.053*
H11B	−0.1272	0.4963	0.6327	0.053*
C12	−0.0299 (4)	0.4971 (3)	0.4978 (3)	0.0436 (8)
H12A	−0.1107	0.5520	0.4560	0.052*
H12B	−0.0775	0.4166	0.4855	0.052*
C13	0.1535 (4)	0.5029 (3)	0.4636 (2)	0.0326 (6)
C14	0.2766 (4)	0.5824 (3)	0.5383 (2)	0.0342 (7)
C15	0.4123 (4)	0.6502 (3)	0.4967 (3)	0.0453 (8)
H15A	0.5203	0.6709	0.5452	0.054*
C16	0.4339 (4)	0.6307 (3)	0.3897 (3)	0.0448 (8)
C17	0.1252 (4)	0.5634 (3)	0.3577 (2)	0.0399 (7)
H17A	0.0622	0.6394	0.3616	0.048*
C18	0.0223 (4)	0.4901 (3)	0.2732 (2)	0.0443 (8)
C19	0.0916 (6)	0.4112 (4)	0.2063 (3)	0.0662 (11)
H19A	0.2103	0.3919	0.2085	0.079*
C20	−0.0468 (8)	0.3705 (5)	0.1401 (3)	0.0748 (13)
H20A	−0.0388	0.3184	0.0867	0.090*
C21	−0.1544 (5)	0.4886 (4)	0.2420 (3)	0.0574 (10)
H21A	−0.2344	0.5323	0.2721	0.069*
C22	0.3961 (6)	0.3883 (4)	1.0151 (3)	0.0642 (11)
H22A	0.4106	0.3417	1.0766	0.096*
H22B	0.3015	0.4451	1.0143	0.096*
H22C	0.5043	0.4306	1.0122	0.096*
C23	0.5000 (6)	0.2108 (5)	0.9290 (3)	0.0732 (12)
H23A	0.4982	0.1591	0.9864	0.110*
H23B	0.6126	0.2510	0.9371	0.110*
H23C	0.4823	0.1639	0.8677	0.110*
C24	0.1085 (5)	0.5429 (4)	0.8538 (3)	0.0530 (9)
H24A	0.0198	0.5943	0.8157	0.079*
H24B	0.2149	0.5882	0.8767	0.079*
H24C	0.0657	0.5110	0.9117	0.079*
C25	0.3216 (6)	0.6778 (3)	0.7107 (3)	0.0587 (10)
H25A	0.4090	0.7265	0.6869	0.088*
H25B	0.3570	0.6643	0.7826	0.088*
H25C	0.2091	0.7183	0.6978	0.088*
C26	0.2393 (5)	0.3790 (3)	0.4574 (2)	0.0438 (8)
H26A	0.3440	0.3874	0.4280	0.066*
H26B	0.1567	0.3267	0.4156	0.066*
H26C	0.2706	0.3456	0.5245	0.066*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.110 (2)	0.094 (3)	0.0705 (19)	−0.023 (2)	0.0160 (17)	0.040 (2)
O2	0.0319 (12)	0.102 (2)	0.0614 (16)	0.0095 (14)	0.0169 (12)	0.0213 (16)
O5	0.0501 (14)	0.0780 (19)	0.0634 (17)	−0.0167 (14)	0.0247 (12)	0.0089 (15)
O3	0.0663 (15)	0.0293 (12)	0.0528 (14)	−0.0011 (11)	0.0190 (12)	0.0026 (11)
O4	0.0474 (13)	0.0593 (16)	0.0405 (13)	−0.0092 (12)	0.0122 (10)	0.0064 (11)
O6	0.080 (2)	0.089 (2)	0.0566 (18)	−0.0281 (19)	−0.0088 (15)	0.0046 (17)
C1	0.0335 (15)	0.0342 (15)	0.0353 (15)	0.0001 (13)	0.0120 (12)	−0.0038 (13)
C2	0.0386 (18)	0.050 (2)	0.0392 (17)	−0.0049 (15)	0.0147 (14)	−0.0037 (16)
C3	0.055 (2)	0.049 (2)	0.047 (2)	−0.0187 (17)	0.0235 (17)	−0.0053 (17)
C4	0.076 (3)	0.045 (2)	0.0430 (19)	−0.0054 (19)	0.0179 (18)	0.0047 (17)
C5	0.053 (2)	0.051 (2)	0.0330 (17)	0.0027 (17)	0.0057 (15)	0.0053 (15)
C6	0.0361 (17)	0.0392 (17)	0.0365 (16)	0.0007 (14)	0.0077 (13)	−0.0017 (14)
C7	0.0368 (18)	0.074 (3)	0.0456 (19)	−0.0034 (18)	0.0015 (14)	0.0102 (19)
C8	0.0249 (15)	0.062 (2)	0.0490 (19)	−0.0151 (15)	0.0050 (14)	0.0057 (17)
C9	0.0344 (16)	0.0349 (17)	0.0400 (17)	−0.0066 (13)	0.0106 (13)	−0.0007 (14)
C10	0.0267 (14)	0.0316 (16)	0.0356 (15)	0.0018 (12)	0.0093 (12)	−0.0012 (12)
C11	0.0308 (16)	0.057 (2)	0.0469 (19)	0.0072 (15)	0.0115 (14)	0.0106 (16)
C12	0.0299 (17)	0.053 (2)	0.0463 (18)	0.0005 (15)	0.0042 (13)	0.0118 (16)
C13	0.0320 (15)	0.0308 (15)	0.0347 (15)	0.0002 (13)	0.0051 (12)	0.0025 (13)
C14	0.0341 (16)	0.0293 (16)	0.0400 (17)	0.0027 (13)	0.0087 (13)	0.0027 (14)
C15	0.0450 (18)	0.0440 (19)	0.0474 (19)	−0.0151 (16)	0.0092 (15)	0.0049 (16)
C16	0.046 (2)	0.0406 (19)	0.049 (2)	−0.0060 (15)	0.0116 (16)	0.0112 (16)
C17	0.0345 (16)	0.0439 (18)	0.0420 (17)	0.0019 (15)	0.0092 (13)	0.0075 (15)
C18	0.051 (2)	0.0437 (19)	0.0367 (17)	−0.0012 (16)	0.0046 (15)	0.0097 (15)
C19	0.077 (3)	0.075 (3)	0.048 (2)	−0.003 (2)	0.013 (2)	−0.005 (2)
C20	0.104 (4)	0.071 (3)	0.048 (2)	−0.015 (3)	0.010 (2)	−0.010 (2)
C21	0.057 (2)	0.063 (3)	0.049 (2)	−0.004 (2)	0.0003 (17)	0.0036 (19)
C22	0.074 (3)	0.079 (3)	0.0351 (18)	−0.002 (2)	−0.0014 (18)	0.001 (2)
C23	0.079 (3)	0.076 (3)	0.062 (2)	0.022 (3)	0.006 (2)	0.021 (2)
C24	0.062 (2)	0.050 (2)	0.052 (2)	0.0065 (18)	0.0248 (18)	−0.0042 (18)
C25	0.082 (3)	0.049 (2)	0.046 (2)	−0.024 (2)	0.0169 (19)	−0.0066 (18)
C26	0.051 (2)	0.0404 (19)	0.0398 (18)	0.0012 (16)	0.0091 (15)	−0.0004 (15)

Geometric parameters (Å, º)

O1—C4	1.210 (4)	C11—H11B	0.9700
O2—C8	1.211 (4)	C12—C13	1.556 (4)
O5—C16	1.195 (4)	C12—H12A	0.9700
O3—C15	1.431 (4)	C12—H12B	0.9700
O3—C14	1.453 (4)	C13—C14	1.523 (4)
O4—C16	1.340 (4)	C13—C26	1.536 (4)
O4—C17	1.464 (4)	C13—C17	1.545 (4)
O6—C20	1.349 (6)	C14—C15	1.473 (4)
O6—C21	1.357 (5)	C15—C16	1.483 (5)
C1—C2	1.522 (4)	C15—H15A	0.9800
C1—C6	1.548 (4)	C17—C18	1.495 (5)
C1—C10	1.548 (4)	C17—H17A	0.9800
C1—C24	1.550 (5)	C18—C21	1.341 (5)
C2—C3	1.318 (5)	C18—C19	1.422 (5)
C2—H2A	0.9300	C19—C20	1.330 (6)
C3—C4	1.462 (5)	C19—H19A	0.9300
C3—H3A	0.9300	C20—H20A	0.9300
C4—C5	1.529 (5)	C21—H21A	0.9300
C5—C23	1.535 (6)	C22—H22A	0.9600
C5—C22	1.538 (5)	C22—H22B	0.9600
C5—C6	1.552 (4)	C22—H22C	0.9600
C6—C7	1.540 (5)	C23—H23A	0.9600
C6—H6A	0.9800	C23—H23B	0.9600
C7—C8	1.507 (5)	C23—H23C	0.9600
C7—H7A	0.9700	C24—H24A	0.9600
C7—H7B	0.9700	C24—H24B	0.9600
C8—C9	1.517 (5)	C24—H24C	0.9600
C9—C25	1.542 (5)	C25—H25A	0.9600
C9—C14	1.552 (4)	C25—H25B	0.9600
C9—C10	1.579 (4)	C25—H25C	0.9600
C10—C11	1.525 (4)	C26—H26A	0.9600
C10—H10A	0.9800	C26—H26B	0.9600
C11—C12	1.530 (5)	C26—H26C	0.9600
C11—H11A	0.9700
C15—O3—C14	61.4 (2)	C14—C13—C12	108.5 (2)
C16—O4—C17	121.1 (2)	C26—C13—C12	113.4 (3)
C20—O6—C21	106.0 (3)	C17—C13—C12	107.7 (2)
C2—C1—C6	105.4 (3)	O3—C14—C15	58.6 (2)
C2—C1—C10	108.9 (2)	O3—C14—C13	111.5 (2)
C6—C1—C10	105.6 (2)	C15—C14—C13	116.5 (3)
C2—C1—C24	105.2 (2)	O3—C14—C9	114.5 (2)
C6—C1—C24	117.6 (3)	C15—C14—C9	119.5 (3)
C10—C1—C24	113.7 (3)	C13—C14—C9	120.0 (2)
C3—C2—C1	123.0 (3)	O3—C15—C14	60.00 (19)
C3—C2—H2A	118.5	O3—C15—C16	116.7 (3)
C1—C2—H2A	118.5	C14—C15—C16	119.9 (3)
C2—C3—C4	123.4 (3)	O3—C15—H15A	116.1
C2—C3—H3A	118.3	C14—C15—H15A	116.1
C4—C3—H3A	118.3	C16—C15—H15A	116.1
O1—C4—C3	120.2 (4)	O5—C16—O4	120.0 (3)
O1—C4—C5	120.2 (4)	O5—C16—C15	122.6 (3)
C3—C4—C5	119.5 (3)	O4—C16—C15	117.4 (3)
C4—C5—C23	107.2 (3)	O4—C17—C18	104.4 (2)
C4—C5—C22	108.1 (3)	O4—C17—C13	112.4 (2)
C23—C5—C22	108.1 (3)	C18—C17—C13	114.8 (3)
C4—C5—C6	109.2 (3)	O4—C17—H17A	108.3
C23—C5—C6	109.8 (3)	C18—C17—H17A	108.3
C22—C5—C6	114.3 (3)	C13—C17—H17A	108.3
C7—C6—C1	113.0 (3)	C21—C18—C19	105.6 (4)
C7—C6—C5	113.4 (3)	C21—C18—C17	127.1 (3)
C1—C6—C5	116.4 (2)	C19—C18—C17	127.2 (3)
C7—C6—H6A	104.1	C20—C19—C18	106.5 (4)
C1—C6—H6A	104.1	C20—C19—H19A	126.8
C5—C6—H6A	104.1	C18—C19—H19A	126.8
C8—C7—C6	110.2 (3)	C19—C20—O6	111.1 (4)
C8—C7—H7A	109.6	C19—C20—H20A	124.5
C6—C7—H7A	109.6	O6—C20—H20A	124.5
C8—C7—H7B	109.6	C18—C21—O6	110.8 (4)
C6—C7—H7B	109.6	C18—C21—H21A	124.6
H7A—C7—H7B	108.1	O6—C21—H21A	124.6
O2—C8—C7	121.8 (3)	C5—C22—H22A	109.5
O2—C8—C9	123.4 (3)	C5—C22—H22B	109.5
C7—C8—C9	114.7 (3)	H22A—C22—H22B	109.5
C8—C9—C25	108.6 (3)	C5—C22—H22C	109.5
C8—C9—C14	113.5 (2)	H22A—C22—H22C	109.5
C25—C9—C14	107.8 (3)	H22B—C22—H22C	109.5
C8—C9—C10	105.1 (2)	C5—C23—H23A	109.5
C25—C9—C10	114.9 (3)	C5—C23—H23B	109.5
C14—C9—C10	107.0 (2)	H23A—C23—H23B	109.5
C11—C10—C1	120.2 (2)	C5—C23—H23C	109.5
C11—C10—C9	107.2 (3)	H23A—C23—H23C	109.5
C1—C10—C9	115.1 (2)	H23B—C23—H23C	109.5
C11—C10—H10A	104.2	C1—C24—H24A	109.5
C1—C10—H10A	104.2	C1—C24—H24B	109.5
C9—C10—H10A	104.2	H24A—C24—H24B	109.5
C10—C11—C12	108.8 (3)	C1—C24—H24C	109.5
C10—C11—H11A	109.9	H24A—C24—H24C	109.5
C12—C11—H11A	109.9	H24B—C24—H24C	109.5
C10—C11—H11B	109.9	C9—C25—H25A	109.5
C12—C11—H11B	109.9	C9—C25—H25B	109.5
H11A—C11—H11B	108.3	H25A—C25—H25B	109.5
C11—C12—C13	114.1 (3)	C9—C25—H25C	109.5
C11—C12—H12A	108.7	H25A—C25—H25C	109.5
C13—C12—H12A	108.7	H25B—C25—H25C	109.5
C11—C12—H12B	108.7	C13—C26—H26A	109.5
C13—C12—H12B	108.7	C13—C26—H26B	109.5
H12A—C12—H12B	107.6	H26A—C26—H26B	109.5
C14—C13—C26	109.7 (2)	C13—C26—H26C	109.5
C14—C13—C17	108.2 (2)	H26A—C26—H26C	109.5
C26—C13—C17	109.3 (2)	H26B—C26—H26C	109.5
C6—C1—C2—C3	32.8 (4)	C15—O3—C14—C13	−108.7 (3)
C10—C1—C2—C3	145.7 (3)	C15—O3—C14—C9	110.9 (3)
C24—C1—C2—C3	−92.1 (4)	C26—C13—C14—O3	151.2 (2)
C1—C2—C3—C4	−1.0 (5)	C17—C13—C14—O3	32.0 (3)
C2—C3—C4—O1	166.4 (4)	C12—C13—C14—O3	−84.5 (3)
C2—C3—C4—C5	−11.9 (5)	C26—C13—C14—C15	86.6 (3)
O1—C4—C5—C23	52.6 (5)	C17—C13—C14—C15	−32.6 (4)
C3—C4—C5—C23	−129.0 (4)	C12—C13—C14—C15	−149.1 (3)
O1—C4—C5—C22	−63.7 (5)	C26—C13—C14—C9	−70.9 (3)
C3—C4—C5—C22	114.7 (4)	C17—C13—C14—C9	169.9 (2)
O1—C4—C5—C6	171.5 (4)	C12—C13—C14—C9	53.4 (3)
C3—C4—C5—C6	−10.2 (4)	C8—C9—C14—O3	−127.0 (3)
C2—C1—C6—C7	170.8 (3)	C25—C9—C14—O3	−6.6 (4)
C10—C1—C6—C7	55.6 (3)	C10—C9—C14—O3	117.5 (3)
C24—C1—C6—C7	−72.4 (3)	C8—C9—C14—C15	−60.6 (4)
C2—C1—C6—C5	−55.4 (3)	C25—C9—C14—C15	59.8 (4)
C10—C1—C6—C5	−170.6 (3)	C10—C9—C14—C15	−176.1 (3)
C24—C1—C6—C5	61.3 (4)	C8—C9—C14—C13	96.3 (3)
C4—C5—C6—C7	178.8 (3)	C25—C9—C14—C13	−143.4 (3)
C23—C5—C6—C7	−64.0 (4)	C10—C9—C14—C13	−19.2 (3)
C22—C5—C6—C7	57.7 (4)	C14—O3—C15—C16	110.7 (3)
C4—C5—C6—C1	45.2 (4)	C13—C14—C15—O3	100.1 (3)
C23—C5—C6—C1	162.4 (3)	C9—C14—C15—O3	−102.2 (3)
C22—C5—C6—C1	−75.9 (4)	O3—C14—C15—C16	−105.5 (4)
C1—C6—C7—C8	−56.3 (4)	C13—C14—C15—C16	−5.4 (5)
C5—C6—C7—C8	168.5 (3)	C9—C14—C15—C16	152.3 (3)
C6—C7—C8—O2	−119.2 (4)	C17—O4—C16—O5	177.5 (3)
C6—C7—C8—C9	57.6 (4)	C17—O4—C16—C15	−0.7 (5)
O2—C8—C9—C25	−116.2 (4)	O3—C15—C16—O5	137.5 (4)
C7—C8—C9—C25	67.0 (4)	C14—C15—C16—O5	−153.4 (3)
O2—C8—C9—C14	3.7 (5)	O3—C15—C16—O4	−44.4 (4)
C7—C8—C9—C14	−173.0 (3)	C14—C15—C16—O4	24.7 (5)
O2—C8—C9—C10	120.4 (4)	C16—O4—C17—C18	−165.2 (3)
C7—C8—C9—C10	−56.4 (4)	C16—O4—C17—C13	−40.1 (4)
C2—C1—C10—C11	58.0 (4)	C14—C13—C17—O4	54.8 (3)
C6—C1—C10—C11	170.8 (3)	C26—C13—C17—O4	−64.7 (3)
C24—C1—C10—C11	−58.9 (4)	C12—C13—C17—O4	171.8 (3)
C2—C1—C10—C9	−171.4 (2)	C14—C13—C17—C18	173.9 (3)
C6—C1—C10—C9	−58.6 (3)	C26—C13—C17—C18	54.5 (3)
C24—C1—C10—C9	71.7 (3)	C12—C13—C17—C18	−69.1 (3)
C8—C9—C10—C11	−164.8 (3)	O4—C17—C18—C21	−147.3 (3)
C25—C9—C10—C11	75.9 (3)	C13—C17—C18—C21	89.2 (4)
C14—C9—C10—C11	−43.8 (3)	O4—C17—C18—C19	29.9 (5)
C8—C9—C10—C1	58.6 (3)	C13—C17—C18—C19	−93.6 (4)
C25—C9—C10—C1	−60.7 (4)	C21—C18—C19—C20	1.0 (5)
C14—C9—C10—C1	179.6 (2)	C17—C18—C19—C20	−176.7 (3)
C1—C10—C11—C12	−150.9 (3)	C18—C19—C20—O6	−1.5 (5)
C9—C10—C11—C12	75.1 (3)	C21—O6—C20—C19	1.5 (5)
C10—C11—C12—C13	−38.9 (4)	C19—C18—C21—O6	−0.1 (4)
C11—C12—C13—C14	−21.1 (4)	C17—C18—C21—O6	177.6 (3)
C11—C12—C13—C26	101.0 (3)	C20—O6—C21—C18	−0.8 (4)
C11—C12—C13—C17	−138.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···O2^i	0.97	2.35	3.288 (4)	162
C21—H21A···O5^i	0.93	2.43	3.361 (5)	176
C23—H23A···O1	0.96	2.50	2.846 (6)	101

Symmetry code: (i) x−1, y, z.