seco-Dukunolide F: a new tetra­nortriterpenoid from Lansium domesticum Corr.

The title compound, methyl 2-[4-(3-fur­yl)-6b,10a-dihydr­oxy-3a,7,9,9-tetra­methyl-6,10-dioxo-2,3,3a,6b,7,8,9,10,10a,11-deca­hydro-1aH,4H,6H-benzo[h][1]benzoxireno[3,2,1a-de]isochro­men-8-yl]acetate, C₂₇H₃₂O₉, is a new tetra­nor­tri­ter­pen­oid which was isolated for the first time from the seeds of Lansium domesticum Coor. The four six-membered rings adopt chair, boat, envelope and screw-boat conformations. The furan substituent is planar and is attached equatorially to the lactone ring. O—H...O hydrogen bonds link the mol­ecules into chains along [100] and adjacent chains are inter­connected by C—H...O inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.042
• wR factor = 0.120
• Data-to-parameter ratio = 9.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.36 Ratio
PLAT230_ALERT_2_B Hirshfeld Test Diff for    O5     -   C19     ..      20.58 su

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.44 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O5     -   C18     ..       5.03 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O5

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           27.00
           From the CIF: _reflns_number_total               2973
           Count of symmetry unique reflns         2979
           Completeness (_total/calc)             99.80%
           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
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15    = .          R

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

   9 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

Author Response: K. Chantrapromma and K. Chaiyadej are involved in the extraction, crystallisation and bioactivity testing of the title compound. X.-L Yu is involved in data collection at Sun Yat-Sen University. H. K. Fun, S. Chantrapromma and N. Boonnak are involved in structure determination, literature survey and write-up the manuscript. All co-authors are involved in the preparing of this manuscript.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

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).

methyl 2-[4-(3-furyl)-6 b,10a-dihydroxy-3a,7,9,9- tetramethyl-6,10-dioxo-2,3,3a,6 b,7,8,9,10,10a,11-decahydro- 1aH,4H,6H-benzo[h][1]benzoxireno[3,2,1a-de]isochromen- 8-yl]acetate

Crystal data

C27H32O9	Dx = 1.385 Mg m^−3
Mr = 500.53	Melting point = 508–510 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2973 reflections
a = 7.9634 (5) Å	θ = 1.7–27.0°
b = 14.6700 (9) Å	µ = 0.10 mm^−1
c = 20.5420 (13) Å	T = 297 K
V = 2399.8 (3) Å^3	Block, colourless
Z = 4	0.50 × 0.39 × 0.34 mm
F(000) = 1064

Data collection

Siemens SMART CCD area-detector diffractometer	2973 independent reflections
Radiation source: fine-focus sealed tube	2814 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 8.33 pixels mm^-1	θmax = 27.0°, θmin = 1.7°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −18→16
Tmin = 0.952, Tmax = 0.965	l = −18→26
14158 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.120	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0826P)^2 + 0.3239P] where P = (Fo^2 + 2Fc^2)/3
2973 reflections	(Δ/σ)max = 0.001
332 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.21 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	0.3417 (3)	0.42137 (16)	0.94558 (8)	0.0573 (5)
O2	−0.0711 (2)	0.67442 (11)	0.71401 (8)	0.0439 (4)
O3	0.1010 (3)	0.73760 (11)	0.78354 (10)	0.0545 (5)
O4	0.3539 (2)	0.41907 (12)	0.67264 (9)	0.0487 (4)
O5	−0.4622 (3)	0.6333 (2)	0.55878 (12)	0.0829 (8)
O6	0.8865 (2)	0.63985 (16)	0.90276 (11)	0.0609 (5)
O7	0.7483 (3)	0.65404 (16)	0.99688 (9)	0.0663 (6)
O8	0.0867 (2)	0.45683 (14)	0.87279 (10)	0.0518 (5)
H8	0.1006	0.4433	0.9111	0.078*
O9	0.2410 (2)	0.61846 (11)	0.87195 (7)	0.0369 (3)
H9	0.1402	0.6201	0.8799	0.055*
C1	0.4535 (3)	0.57717 (13)	0.79440 (10)	0.0302 (4)
H1	0.4736	0.5336	0.7591	0.036*
C2	0.5847 (3)	0.55552 (14)	0.84822 (10)	0.0311 (4)
H2	0.6949	0.5597	0.8273	0.037*
C3	0.5687 (3)	0.45551 (14)	0.87311 (11)	0.0351 (5)
C4	0.3840 (3)	0.44180 (14)	0.89109 (10)	0.0357 (5)
C5	0.2447 (3)	0.46152 (14)	0.84100 (10)	0.0349 (4)
C6	0.2696 (3)	0.56225 (13)	0.81715 (9)	0.0305 (4)
C7	0.1472 (3)	0.57899 (14)	0.76116 (10)	0.0324 (4)
C8	0.1266 (3)	0.51765 (14)	0.71362 (10)	0.0333 (4)
C9	0.2140 (3)	0.42807 (14)	0.71819 (11)	0.0355 (4)
C10	0.2387 (4)	0.39123 (15)	0.78561 (11)	0.0428 (5)
H10A	0.3427	0.3569	0.7863	0.051*
H10B	0.1482	0.3488	0.7947	0.051*
C11	0.2032 (3)	0.36382 (16)	0.66361 (12)	0.0454 (6)
H11	0.2145	0.2993	0.6752	0.055*
C12	0.0932 (4)	0.3833 (2)	0.60616 (13)	0.0576 (7)
H12A	0.0439	0.3269	0.5907	0.069*
H12B	0.1607	0.4087	0.5713	0.069*
C13	−0.0456 (4)	0.44992 (17)	0.62364 (13)	0.0462 (6)
H13A	−0.1218	0.4209	0.6541	0.055*
H13B	−0.1088	0.4646	0.5847	0.055*
C14	0.0207 (3)	0.53885 (15)	0.65406 (10)	0.0352 (5)
C15	−0.1284 (3)	0.59405 (15)	0.67925 (11)	0.0375 (5)
H15	−0.1918	0.5558	0.7097	0.045*
C16	0.0602 (3)	0.66868 (15)	0.75522 (11)	0.0374 (5)
C17	−0.2467 (3)	0.62764 (17)	0.62785 (11)	0.0429 (5)
C18	−0.3890 (4)	0.5846 (2)	0.60684 (14)	0.0579 (7)
H18	−0.4295	0.5298	0.6232	0.070*
C19	−0.3648 (4)	0.7108 (2)	0.54919 (13)	0.0539 (7)
H19	−0.3857	0.7567	0.5190	0.065*
C20	−0.2354 (4)	0.70785 (19)	0.59097 (13)	0.0537 (7)
H20	−0.1518	0.7518	0.5948	0.064*
C21	0.5865 (3)	0.62539 (16)	0.90388 (11)	0.0377 (5)
H21A	0.5461	0.6834	0.8876	0.045*
H21B	0.5099	0.6054	0.9377	0.045*
C22	0.7582 (3)	0.63864 (15)	0.93302 (12)	0.0409 (5)
C23	0.9047 (6)	0.6673 (4)	1.0301 (2)	0.1045 (18)
H23A	0.8845	0.6727	1.0760	0.157*
H23B	0.9573	0.7220	1.0144	0.157*
H23C	0.9770	0.6162	1.0221	0.157*
C24	0.6749 (4)	0.4372 (2)	0.93380 (13)	0.0525 (6)
H24A	0.6700	0.3736	0.9444	0.079*
H24B	0.6321	0.4724	0.9696	0.079*
H24C	0.7893	0.4543	0.9255	0.079*
C25	0.6328 (4)	0.39005 (18)	0.82026 (14)	0.0530 (6)
H25A	0.5990	0.3289	0.8307	0.079*
H25B	0.7531	0.3931	0.8182	0.079*
H25C	0.5863	0.4072	0.7789	0.079*
C26	0.4792 (3)	0.67209 (16)	0.76549 (12)	0.0411 (5)
H26A	0.4241	0.6756	0.7240	0.062*
H26B	0.5971	0.6834	0.7600	0.062*
H26C	0.4325	0.7170	0.7943	0.062*
C27	0.1257 (3)	0.5937 (2)	0.60509 (11)	0.0473 (6)
H27A	0.1526	0.6521	0.6233	0.071*
H27B	0.0626	0.6019	0.5657	0.071*
H27C	0.2275	0.5612	0.5956	0.071*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0551 (11)	0.0791 (14)	0.0376 (9)	−0.0112 (11)	−0.0024 (9)	0.0142 (9)
O2	0.0460 (9)	0.0398 (8)	0.0459 (8)	0.0130 (8)	−0.0100 (8)	−0.0092 (7)
O3	0.0607 (12)	0.0374 (8)	0.0654 (11)	0.0095 (9)	−0.0170 (10)	−0.0152 (8)
O4	0.0477 (10)	0.0460 (9)	0.0524 (9)	0.0068 (8)	0.0031 (8)	−0.0095 (8)
O5	0.0605 (14)	0.115 (2)	0.0735 (15)	0.0209 (16)	−0.0235 (12)	−0.0099 (15)
O6	0.0365 (9)	0.0694 (13)	0.0766 (13)	−0.0076 (9)	0.0001 (10)	−0.0141 (11)
O7	0.0734 (14)	0.0827 (15)	0.0428 (9)	−0.0353 (13)	−0.0116 (10)	−0.0063 (9)
O8	0.0376 (9)	0.0617 (11)	0.0561 (11)	−0.0122 (9)	0.0038 (8)	0.0099 (9)
O9	0.0314 (7)	0.0451 (8)	0.0343 (7)	−0.0004 (7)	0.0018 (6)	−0.0121 (6)
C1	0.0329 (10)	0.0286 (9)	0.0291 (9)	−0.0005 (8)	0.0023 (8)	−0.0029 (7)
C2	0.0275 (9)	0.0340 (10)	0.0319 (9)	−0.0008 (8)	0.0013 (8)	−0.0038 (8)
C3	0.0362 (11)	0.0331 (10)	0.0360 (10)	0.0008 (9)	−0.0037 (9)	0.0006 (8)
C4	0.0430 (12)	0.0308 (9)	0.0333 (10)	−0.0033 (9)	−0.0048 (9)	0.0014 (8)
C5	0.0331 (10)	0.0365 (10)	0.0349 (10)	−0.0049 (9)	−0.0027 (9)	0.0028 (8)
C6	0.0318 (10)	0.0297 (9)	0.0299 (9)	0.0000 (8)	−0.0014 (8)	−0.0040 (7)
C7	0.0325 (10)	0.0302 (9)	0.0346 (9)	0.0006 (8)	−0.0026 (8)	−0.0022 (8)
C8	0.0345 (10)	0.0322 (9)	0.0334 (9)	0.0006 (8)	−0.0022 (9)	−0.0009 (8)
C9	0.0365 (11)	0.0310 (9)	0.0389 (10)	0.0022 (8)	−0.0063 (9)	−0.0043 (8)
C10	0.0548 (14)	0.0291 (9)	0.0447 (11)	−0.0038 (10)	−0.0163 (11)	0.0007 (9)
C11	0.0524 (14)	0.0370 (11)	0.0468 (12)	0.0066 (11)	−0.0092 (11)	−0.0107 (10)
C12	0.0745 (19)	0.0511 (14)	0.0473 (13)	0.0182 (14)	−0.0175 (14)	−0.0188 (11)
C13	0.0501 (14)	0.0436 (12)	0.0448 (12)	0.0044 (11)	−0.0175 (11)	−0.0093 (10)
C14	0.0372 (11)	0.0355 (10)	0.0328 (9)	0.0042 (9)	−0.0043 (9)	−0.0043 (8)
C15	0.0345 (10)	0.0415 (11)	0.0364 (10)	0.0016 (9)	−0.0022 (9)	−0.0018 (9)
C16	0.0400 (11)	0.0330 (10)	0.0393 (11)	0.0044 (9)	−0.0028 (10)	−0.0031 (9)
C17	0.0370 (11)	0.0519 (13)	0.0399 (11)	0.0091 (11)	−0.0013 (10)	−0.0062 (10)
C18	0.0403 (13)	0.0752 (19)	0.0584 (16)	0.0004 (13)	−0.0068 (12)	0.0011 (14)
C19	0.0569 (16)	0.0574 (15)	0.0475 (13)	0.0195 (14)	−0.0149 (13)	0.0008 (11)
C20	0.0604 (16)	0.0499 (13)	0.0509 (14)	0.0132 (13)	−0.0118 (14)	−0.0016 (11)
C21	0.0346 (10)	0.0408 (11)	0.0379 (10)	−0.0014 (9)	0.0002 (9)	−0.0097 (9)
C22	0.0421 (13)	0.0334 (10)	0.0473 (12)	−0.0076 (10)	−0.0056 (11)	−0.0042 (9)
C23	0.113 (4)	0.124 (4)	0.076 (2)	−0.071 (3)	−0.053 (3)	0.022 (2)
C24	0.0473 (14)	0.0549 (14)	0.0554 (14)	−0.0043 (12)	−0.0184 (12)	0.0130 (12)
C25	0.0540 (15)	0.0404 (12)	0.0646 (16)	0.0093 (12)	0.0039 (13)	−0.0078 (12)
C26	0.0438 (12)	0.0363 (11)	0.0432 (12)	−0.0018 (10)	0.0031 (10)	0.0057 (10)
C27	0.0441 (13)	0.0621 (15)	0.0358 (11)	0.0069 (12)	0.0034 (10)	0.0052 (11)

Geometric parameters (Å, º)

O1—C4	1.207 (3)	C11—C12	1.497 (3)
O2—C16	1.348 (3)	C11—H11	0.98
O2—C15	1.452 (3)	C12—C13	1.518 (4)
O3—C16	1.211 (3)	C12—H12A	0.97
O4—C11	1.460 (3)	C12—H12B	0.97
O4—C9	1.461 (3)	C13—C14	1.540 (3)
O5—C18	1.351 (4)	C13—H13A	0.97
O5—C19	1.389 (4)	C13—H13B	0.97
O6—C22	1.196 (3)	C14—C15	1.528 (3)
O7—C22	1.333 (3)	C14—C27	1.535 (3)
O7—C23	1.433 (4)	C15—C17	1.499 (3)
O8—C5	1.420 (3)	C15—H15	0.98
O8—H8	0.82	C17—C18	1.367 (4)
O9—C6	1.414 (2)	C17—C20	1.402 (4)
O9—H9	0.82	C18—H18	0.93
C1—C26	1.528 (3)	C19—C20	1.342 (4)
C1—C6	1.553 (3)	C19—H19	0.93
C1—C2	1.553 (3)	C20—H20	0.93
C1—H1	0.98	C21—C22	1.506 (3)
C2—C21	1.536 (3)	C21—H21A	0.97
C2—C3	1.559 (3)	C21—H21B	0.97
C2—H2	0.98	C23—H23A	0.96
C3—C24	1.530 (3)	C23—H23B	0.96
C3—C4	1.530 (3)	C23—H23C	0.96
C3—C25	1.537 (3)	C24—H24A	0.96
C4—C5	1.540 (3)	C24—H24B	0.96
C5—C10	1.536 (3)	C24—H24C	0.96
C5—C6	1.569 (3)	C25—H25A	0.96
C6—C7	1.528 (3)	C25—H25B	0.96
C7—C8	1.338 (3)	C25—H25C	0.96
C7—C16	1.492 (3)	C26—H26A	0.96
C8—C9	1.490 (3)	C26—H26B	0.96
C8—C14	1.518 (3)	C26—H26C	0.96
C9—C11	1.467 (3)	C27—H27A	0.96
C9—C10	1.499 (3)	C27—H27B	0.96
C10—H10A	0.97	C27—H27C	0.96
C10—H10B	0.97
C16—O2—C15	120.11 (17)	C14—C13—H13A	109.0
C11—O4—C9	60.31 (15)	C12—C13—H13B	109.0
C18—O5—C19	107.2 (2)	C14—C13—H13B	109.0
C22—O7—C23	116.1 (3)	H13A—C13—H13B	107.8
C5—O8—H8	109.5	C8—C14—C15	105.50 (17)
C6—O9—H9	109.5	C8—C14—C27	109.46 (19)
C26—C1—C6	111.82 (18)	C15—C14—C27	111.56 (19)
C26—C1—C2	111.91 (18)	C8—C14—C13	110.12 (19)
C6—C1—C2	113.02 (16)	C15—C14—C13	108.7 (2)
C26—C1—H1	106.5	C27—C14—C13	111.4 (2)
C6—C1—H1	106.5	O2—C15—C17	106.07 (18)
C2—C1—H1	106.5	O2—C15—C14	110.68 (18)
C21—C2—C1	113.56 (17)	C17—C15—C14	115.11 (18)
C21—C2—C3	112.63 (17)	O2—C15—H15	108.3
C1—C2—C3	111.78 (17)	C17—C15—H15	108.3
C21—C2—H2	106.1	C14—C15—H15	108.3
C1—C2—H2	106.1	O3—C16—O2	117.2 (2)
C3—C2—H2	106.1	O3—C16—C7	124.9 (2)
C24—C3—C4	108.2 (2)	O2—C16—C7	117.81 (19)
C24—C3—C25	106.4 (2)	C18—C17—C20	105.7 (3)
C4—C3—C25	114.1 (2)	C18—C17—C15	126.3 (3)
C24—C3—C2	112.77 (19)	C20—C17—C15	128.0 (2)
C4—C3—C2	106.34 (17)	O5—C18—C17	110.1 (3)
C25—C3—C2	109.23 (19)	O5—C18—H18	124.9
O1—C4—C3	121.6 (2)	C17—C18—H18	124.9
O1—C4—C5	117.8 (2)	C20—C19—O5	108.2 (3)
C3—C4—C5	120.42 (18)	C20—C19—H19	125.9
O8—C5—C10	106.3 (2)	O5—C19—H19	125.9
O8—C5—C4	108.78 (17)	C19—C20—C17	108.8 (3)
C10—C5—C4	113.04 (19)	C19—C20—H20	125.6
O8—C5—C6	107.52 (18)	C17—C20—H20	125.6
C10—C5—C6	113.87 (17)	C22—C21—C2	113.00 (19)
C4—C5—C6	107.14 (17)	C22—C21—H21A	109.0
O9—C6—C7	113.77 (17)	C2—C21—H21A	109.0
O9—C6—C1	108.00 (16)	C22—C21—H21B	109.0
C7—C6—C1	110.65 (16)	C2—C21—H21B	109.0
O9—C6—C5	106.28 (16)	H21A—C21—H21B	107.8
C7—C6—C5	107.82 (16)	O6—C22—O7	124.0 (3)
C1—C6—C5	110.23 (16)	O6—C22—C21	124.8 (2)
C8—C7—C16	118.46 (19)	O7—C22—C21	111.1 (2)
C8—C7—C6	121.30 (18)	O7—C23—H23A	109.5
C16—C7—C6	119.98 (18)	O7—C23—H23B	109.5
C7—C8—C9	119.33 (19)	H23A—C23—H23B	109.5
C7—C8—C14	121.23 (19)	O7—C23—H23C	109.5
C9—C8—C14	119.41 (18)	H23A—C23—H23C	109.5
O4—C9—C11	59.82 (16)	H23B—C23—H23C	109.5
O4—C9—C8	113.30 (18)	C3—C24—H24A	109.5
C11—C9—C8	119.39 (19)	C3—C24—H24B	109.5
O4—C9—C10	117.3 (2)	H24A—C24—H24B	109.5
C11—C9—C10	118.81 (19)	C3—C24—H24C	109.5
C8—C9—C10	115.93 (18)	H24A—C24—H24C	109.5
C9—C10—C5	116.50 (18)	H24B—C24—H24C	109.5
C9—C10—H10A	108.2	C3—C25—H25A	109.5
C5—C10—H10A	108.2	C3—C25—H25B	109.5
C9—C10—H10B	108.2	H25A—C25—H25B	109.5
C5—C10—H10B	108.2	C3—C25—H25C	109.5
H10A—C10—H10B	107.3	H25A—C25—H25C	109.5
O4—C11—C9	59.87 (14)	H25B—C25—H25C	109.5
O4—C11—C12	118.3 (2)	C1—C26—H26A	109.5
C9—C11—C12	120.9 (2)	C1—C26—H26B	109.5
O4—C11—H11	115.4	H26A—C26—H26B	109.5
C9—C11—H11	115.4	C1—C26—H26C	109.5
C12—C11—H11	115.4	H26A—C26—H26C	109.5
C11—C12—C13	111.3 (2)	H26B—C26—H26C	109.5
C11—C12—H12A	109.4	C14—C27—H27A	109.5
C13—C12—H12A	109.4	C14—C27—H27B	109.5
C11—C12—H12B	109.4	H27A—C27—H27B	109.5
C13—C12—H12B	109.4	C14—C27—H27C	109.5
H12A—C12—H12B	108.0	H27A—C27—H27C	109.5
C12—C13—C14	113.0 (2)	H27B—C27—H27C	109.5
C12—C13—H13A	109.0
C26—C1—C2—C21	56.5 (2)	O4—C9—C10—C5	112.6 (2)
C6—C1—C2—C21	−70.8 (2)	C11—C9—C10—C5	−178.5 (2)
C26—C1—C2—C3	−174.73 (18)	C8—C9—C10—C5	−25.6 (3)
C6—C1—C2—C3	58.0 (2)	O8—C5—C10—C9	103.5 (2)
C21—C2—C3—C24	−40.9 (3)	C4—C5—C10—C9	−137.2 (2)
C1—C2—C3—C24	−170.1 (2)	C6—C5—C10—C9	−14.6 (3)
C21—C2—C3—C4	77.5 (2)	C9—O4—C11—C12	111.2 (2)
C1—C2—C3—C4	−51.7 (2)	C8—C9—C11—O4	101.4 (2)
C21—C2—C3—C25	−158.9 (2)	C10—C9—C11—O4	−106.6 (2)
C1—C2—C3—C25	71.8 (2)	O4—C9—C11—C12	−107.0 (3)
C24—C3—C4—O1	1.0 (3)	C8—C9—C11—C12	−5.6 (4)
C25—C3—C4—O1	119.2 (3)	C10—C9—C11—C12	146.4 (3)
C2—C3—C4—O1	−120.4 (2)	O4—C11—C12—C13	−92.7 (3)
C24—C3—C4—C5	175.9 (2)	C9—C11—C12—C13	−22.7 (4)
C25—C3—C4—C5	−65.9 (3)	C11—C12—C13—C14	54.3 (3)
C2—C3—C4—C5	54.6 (2)	C7—C8—C14—C15	−38.2 (3)
O1—C4—C5—O8	3.9 (3)	C9—C8—C14—C15	143.9 (2)
C3—C4—C5—O8	−171.21 (19)	C7—C8—C14—C27	81.9 (3)
O1—C4—C5—C10	−113.9 (2)	C9—C8—C14—C27	−96.0 (2)
C3—C4—C5—C10	71.0 (3)	C7—C8—C14—C13	−155.3 (2)
O1—C4—C5—C6	119.9 (2)	C9—C8—C14—C13	26.8 (3)
C3—C4—C5—C6	−55.3 (2)	C12—C13—C14—C8	−56.2 (3)
C26—C1—C6—O9	−69.1 (2)	C12—C13—C14—C15	−171.3 (2)
C2—C1—C6—O9	58.3 (2)	C12—C13—C14—C27	65.4 (3)
C26—C1—C6—C7	56.1 (2)	C16—O2—C15—C17	−167.6 (2)
C2—C1—C6—C7	−176.58 (16)	C16—O2—C15—C14	−42.1 (3)
C26—C1—C6—C5	175.23 (17)	C8—C14—C15—O2	56.4 (2)
C2—C1—C6—C5	−57.4 (2)	C27—C14—C15—O2	−62.3 (2)
O8—C5—C6—O9	51.9 (2)	C13—C14—C15—O2	174.48 (18)
C10—C5—C6—O9	169.34 (19)	C8—C14—C15—C17	176.7 (2)
C4—C5—C6—O9	−64.9 (2)	C27—C14—C15—C17	57.9 (3)
O8—C5—C6—C7	−70.4 (2)	C13—C14—C15—C17	−65.3 (3)
C10—C5—C6—C7	47.0 (2)	C15—O2—C16—O3	−179.0 (2)
C4—C5—C6—C7	172.77 (17)	C15—O2—C16—C7	2.6 (3)
O8—C5—C6—C1	168.67 (16)	C8—C7—C16—O3	−158.8 (3)
C10—C5—C6—C1	−73.9 (2)	C6—C7—C16—O3	15.4 (4)
C4—C5—C6—C1	51.9 (2)	C8—C7—C16—O2	19.3 (3)
O9—C6—C7—C8	−162.1 (2)	C6—C7—C16—O2	−166.4 (2)
C1—C6—C7—C8	76.1 (2)	O2—C15—C17—C18	−144.0 (3)
C5—C6—C7—C8	−44.5 (3)	C14—C15—C17—C18	93.3 (3)
O9—C6—C7—C16	23.8 (3)	O2—C15—C17—C20	36.7 (3)
C1—C6—C7—C16	−98.0 (2)	C14—C15—C17—C20	−86.0 (3)
C5—C6—C7—C16	141.4 (2)	C19—O5—C18—C17	−0.8 (3)
C16—C7—C8—C9	179.3 (2)	C20—C17—C18—O5	1.1 (3)
C6—C7—C8—C9	5.1 (3)	C15—C17—C18—O5	−178.3 (2)
C16—C7—C8—C14	1.4 (3)	C18—O5—C19—C20	0.1 (3)
C6—C7—C8—C14	−172.77 (19)	O5—C19—C20—C17	0.5 (3)
C11—O4—C9—C8	−111.6 (2)	C18—C17—C20—C19	−1.0 (3)
C11—O4—C9—C10	109.1 (2)	C15—C17—C20—C19	178.4 (2)
C7—C8—C9—O4	−107.5 (2)	C1—C2—C21—C22	−147.41 (19)
C14—C8—C9—O4	70.4 (3)	C3—C2—C21—C22	84.2 (2)
C7—C8—C9—C11	−174.8 (2)	C23—O7—C22—O6	−3.7 (5)
C14—C8—C9—C11	3.1 (3)	C23—O7—C22—C21	179.7 (3)
C7—C8—C9—C10	32.4 (3)	C2—C21—C22—O6	38.4 (3)
C14—C8—C9—C10	−149.7 (2)	C2—C21—C22—O7	−145.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8···O1	0.82	2.07	2.575 (3)	119
O9—H9···O6^i	0.82	2.09	2.910 (2)	174
C2—H2···O6	0.98	2.47	2.926 (3)	108
C18—H18···O4^i	0.93	2.58	3.452 (3)	157
C19—H19···O1^ii	0.93	2.55	3.096 (4)	118
C27—H27A···O2	0.96	2.60	2.977 (3)	104

Symmetry codes: (i) x−1, y, z; (ii) −x, y+1/2, −z+3/2.