A rearranged labdane diterpene glycoside

The title compound, 13(R)-9β-methyl-1(10),14-dienefried­labda-13-O-α-L-2′-acetyl­rhamonopyanoside or 3-methyl-5-(1,2,5,5-tetra­methyl-1,2,3,4,4a,5,6,7-octa­hydro­naphth­yl)pent-1-en-3-yl 2-O-acetyl­rhamnopyanoside, C₂₈H₄₆O₆, is a bicyclic diterpenoid glycoside. The rearranged methyl group (from C10 to C9) is in a β orientation and a double bond is formed between C1 and C10 in the rearrangement. The L-rhamnose group on the cyclo­hexane ring is equatorial and the configuration of the C atom to which the methyl­ene group is attached is R. The cyclo­hexene, cyclo­hexane and L-rhamnose rings in the mol­ecule adopt half-chair, chair and chair conformations, respectively. In the crystal structure, mol­ecules are linked by O—H...O hydrogen bonds. The L-2′-acetyl-rhamnose hydr­oxy groups serve as hydrogen-bond donors, forming mol­ecular chains along the b axis.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.038
• wR factor = 0.082
• Data-to-parameter ratio = 10.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.72 Ratio
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C14    -   C15     ..       8.83 su

Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.39 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C27

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           27.09
           From the CIF: _reflns_number_total               3289
           Count of symmetry unique reflns         3289
           Completeness (_total/calc)            100.00%
           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
   2 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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

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Computing details

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 1994; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

3-methyl-5-(1,2,5,5-tetramethyl-1,2,3,4,4a,5,6,7-octahydronaphthyl)pent- 1-en-3-yl 2-O-acetylrhamnopyanoside

Crystal data

C28H46O6	F(000) = 524
Mr = 478.65	Dx = 1.137 Mg m^−3
Monoclinic, P21	Melting point: 420 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 11.542 (2) Å	Cell parameters from 42 reflections
b = 8.793 (2) Å	θ = 2.7–14.3°
c = 14.095 (2) Å	µ = 0.08 mm^−1
β = 102.14 (1)°	T = 293 K
V = 1398.6 (4) Å^3	Prism, colourless
Z = 2	0.58 × 0.40 × 0.16 mm

Data collection

Siemens P4 diffractometer	Rint = 0.020
Radiation source: normal-focus sealed tube	θmax = 27.1°, θmin = 1.5°
Graphite monochromator	h = 0→14
ω scans	k = 0→11
3583 measured reflections	l = −18→17
3289 independent reflections	3 standard reflections every 97 reflections
1841 reflections with I > 2σ(I)	intensity decay: 3.0%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.082	w = 1/[σ^2(Fo^2) + (0.04P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.81	(Δ/σ)max < 0.001
3289 reflections	Δρmax = 0.12 e Å^−3
320 parameters	Δρmin = −0.13 e Å^−3
2 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0125 (13)

Special details

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

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

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.36225 (14)	0.6720 (2)	0.67652 (10)	0.0490 (5)
O2	0.36092 (18)	0.4913 (2)	0.55450 (12)	0.0596 (5)
O3	0.08799 (19)	0.3232 (2)	0.60387 (13)	0.0680 (6)
H3O	0.0635	0.2493	0.5701	0.082*
O4	0.01118 (17)	0.6164 (3)	0.53205 (15)	0.0709 (6)
H4O	−0.0328	0.5519	0.5474	0.085*
O5	0.18951 (18)	0.6820 (2)	0.43272 (11)	0.0631 (6)
O6	0.1872 (2)	0.9349 (3)	0.42272 (15)	0.0792 (7)
C1	0.2812 (2)	0.8781 (4)	1.0021 (2)	0.0544 (8)
C2	0.1991 (3)	1.0113 (4)	0.9892 (2)	0.0709 (9)
H2A	0.2379	1.0980	0.9669	0.085*
H2B	0.1808	1.0377	1.0513	0.085*
C3	0.0843 (3)	0.9771 (4)	0.9164 (2)	0.0677 (9)
H3A	0.0423	1.0715	0.8976	0.081*
H3B	0.0343	0.9131	0.9470	0.081*
C4	0.1073 (2)	0.8971 (3)	0.82555 (19)	0.0580 (8)
C5	0.1711 (2)	0.7450 (3)	0.85551 (18)	0.0455 (7)
H5	0.2066	0.7141	0.8012	0.055*
C6	0.0930 (2)	0.6128 (3)	0.87389 (19)	0.0573 (8)
H6A	0.0301	0.5976	0.8171	0.069*
H6B	0.0566	0.6377	0.9280	0.069*
C7	0.1639 (2)	0.4659 (3)	0.8963 (2)	0.0585 (8)
H7A	0.1881	0.4320	0.8379	0.070*
H7B	0.1129	0.3881	0.9142	0.070*
C8	0.2745 (2)	0.4816 (4)	0.97817 (19)	0.0521 (8)
H8	0.3223	0.3897	0.9771	0.063*
C9	0.3527 (2)	0.6201 (3)	0.96211 (16)	0.0411 (6)
C10	0.2724 (2)	0.7589 (3)	0.94321 (17)	0.0422 (7)
C11	0.4076 (2)	0.5836 (3)	0.87336 (17)	0.0449 (6)
H11A	0.4649	0.5024	0.8911	0.054*
H11B	0.3454	0.5460	0.8214	0.054*
C12	0.4687 (2)	0.7167 (3)	0.83465 (16)	0.0485 (7)
H12A	0.5463	0.7310	0.8762	0.058*
H12B	0.4230	0.8084	0.8383	0.058*
C13	0.4833 (2)	0.6958 (4)	0.72948 (17)	0.0525 (7)
C14	0.5238 (3)	0.8442 (5)	0.6929 (2)	0.0879 (13)
H14	0.4703	0.9244	0.6880	0.105*
C15	0.6204 (4)	0.8740 (7)	0.6682 (2)	0.153 (2)
H15A	0.6778	0.7989	0.6713	0.183*
H15B	0.6341	0.9711	0.6467	0.183*
C16	0.5615 (3)	0.5616 (5)	0.7199 (2)	0.0840 (12)
H16A	0.5260	0.4703	0.7380	0.101*
H16B	0.6379	0.5757	0.7617	0.101*
H16C	0.5704	0.5534	0.6538	0.101*
C17	0.2378 (3)	0.4858 (4)	1.07661 (19)	0.0737 (10)
H17A	0.1938	0.5771	1.0813	0.088*
H17B	0.3074	0.4839	1.1278	0.088*
H17C	0.1894	0.3989	1.0823	0.088*
C18	−0.0106 (3)	0.8719 (5)	0.7529 (2)	0.0892 (12)
H18A	−0.0409	0.9678	0.7260	0.107*
H18B	−0.0668	0.8260	0.7856	0.107*
H18C	0.0021	0.8061	0.7017	0.107*
C19	0.1867 (3)	0.9969 (4)	0.7767 (2)	0.0823 (11)
H19A	0.1974	0.9490	0.7179	0.099*
H19B	0.2624	1.0097	0.8198	0.099*
H19C	0.1502	1.0945	0.7617	0.099*
C20	0.4563 (2)	0.6392 (4)	1.04927 (16)	0.0578 (8)
H20A	0.5073	0.7193	1.0362	0.069*
H20B	0.5002	0.5459	1.0604	0.069*
H20C	0.4261	0.6645	1.1058	0.069*
C21	0.3407 (3)	0.6435 (3)	0.57607 (18)	0.0548 (8)
H21	0.3920	0.7092	0.5466	0.066*
C22	0.2122 (2)	0.6891 (4)	0.53807 (16)	0.0549 (8)
H22	0.1984	0.7924	0.5593	0.066*
C23	0.1316 (2)	0.5784 (3)	0.57355 (18)	0.0505 (7)
H23	0.1431	0.5914	0.6440	0.061*
C24	0.1598 (3)	0.4157 (3)	0.55485 (18)	0.0550 (8)
H24	0.1401	0.3948	0.4850	0.066*
C25	0.2902 (3)	0.3835 (3)	0.5949 (2)	0.0556 (8)
H25	0.3068	0.3956	0.6656	0.067*
C26	0.3282 (3)	0.2264 (4)	0.5707 (3)	0.0904 (12)
H26A	0.3122	0.2137	0.5015	0.109*
H26B	0.2851	0.1515	0.5988	0.109*
H26C	0.4116	0.2142	0.5964	0.109*
C27	0.1794 (2)	0.8131 (4)	0.3839 (2)	0.0558 (7)
C28	0.1572 (3)	0.7892 (4)	0.27674 (19)	0.0821 (11)
H28A	0.1534	0.6822	0.2630	0.098*	0.50
H28B	0.2204	0.8340	0.2516	0.098*	0.50
H28C	0.0834	0.8361	0.2467	0.098*	0.50
H28D	0.1514	0.8860	0.2446	0.098*	0.50
H28E	0.0845	0.7342	0.2559	0.098*	0.50
H28F	0.2214	0.7321	0.2608	0.098*	0.50
H1	0.3451 (15)	0.880 (3)	1.0562 (12)	0.059 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0516 (10)	0.0610 (12)	0.0327 (9)	−0.0048 (10)	0.0052 (8)	−0.0039 (9)
O2	0.0761 (14)	0.0573 (13)	0.0489 (11)	−0.0002 (12)	0.0209 (10)	−0.0087 (10)
O3	0.0878 (15)	0.0541 (14)	0.0628 (12)	−0.0155 (13)	0.0174 (12)	−0.0022 (11)
O4	0.0597 (12)	0.0703 (15)	0.0749 (14)	−0.0019 (12)	−0.0037 (11)	0.0141 (12)
O5	0.1016 (16)	0.0496 (12)	0.0336 (10)	−0.0047 (13)	0.0044 (10)	0.0008 (10)
O6	0.112 (2)	0.0550 (15)	0.0699 (14)	−0.0109 (14)	0.0174 (13)	0.0052 (13)
C1	0.0449 (18)	0.067 (2)	0.0507 (18)	0.0019 (17)	0.0093 (14)	−0.0107 (17)
C2	0.071 (2)	0.067 (2)	0.077 (2)	0.0081 (19)	0.0195 (17)	−0.0248 (18)
C3	0.063 (2)	0.071 (2)	0.0689 (19)	0.0255 (18)	0.0143 (16)	−0.0085 (17)
C4	0.0580 (19)	0.063 (2)	0.0517 (17)	0.0201 (17)	0.0089 (14)	0.0002 (15)
C5	0.0426 (15)	0.0528 (17)	0.0413 (15)	0.0064 (14)	0.0090 (12)	−0.0006 (12)
C6	0.0419 (15)	0.068 (2)	0.0571 (17)	−0.0033 (17)	−0.0007 (13)	0.0011 (16)
C7	0.0569 (18)	0.057 (2)	0.0642 (18)	−0.0100 (16)	0.0175 (15)	0.0037 (16)
C8	0.0474 (18)	0.057 (2)	0.0527 (16)	0.0059 (15)	0.0122 (14)	0.0149 (14)
C9	0.0351 (13)	0.0522 (17)	0.0359 (13)	0.0009 (14)	0.0071 (11)	0.0053 (12)
C10	0.0373 (14)	0.0529 (18)	0.0384 (14)	−0.0008 (13)	0.0124 (12)	0.0016 (13)
C11	0.0405 (14)	0.0490 (17)	0.0447 (14)	0.0090 (14)	0.0077 (11)	0.0029 (13)
C12	0.0438 (14)	0.066 (2)	0.0364 (14)	−0.0014 (15)	0.0102 (12)	−0.0020 (14)
C13	0.0440 (15)	0.075 (2)	0.0406 (14)	−0.0078 (17)	0.0139 (12)	−0.0028 (15)
C14	0.091 (3)	0.126 (4)	0.0501 (19)	−0.055 (3)	0.0228 (18)	−0.007 (2)
C15	0.178 (4)	0.221 (6)	0.070 (2)	−0.111 (5)	0.050 (3)	−0.018 (3)
C16	0.059 (2)	0.135 (4)	0.062 (2)	0.023 (2)	0.0213 (16)	−0.011 (2)
C17	0.0625 (19)	0.102 (3)	0.0606 (18)	0.001 (2)	0.0217 (15)	0.0252 (19)
C18	0.081 (2)	0.100 (3)	0.074 (2)	0.051 (2)	−0.0107 (18)	−0.002 (2)
C19	0.109 (3)	0.066 (2)	0.077 (2)	0.028 (2)	0.032 (2)	0.0172 (19)
C20	0.0500 (16)	0.077 (2)	0.0438 (15)	0.0086 (16)	0.0047 (12)	0.0054 (15)
C21	0.0685 (19)	0.058 (2)	0.0384 (15)	−0.0054 (17)	0.0117 (14)	−0.0060 (14)
C22	0.077 (2)	0.0517 (18)	0.0313 (14)	−0.0003 (18)	0.0016 (13)	−0.0042 (14)
C23	0.0582 (17)	0.0508 (19)	0.0378 (14)	0.0008 (16)	−0.0009 (13)	0.0004 (14)
C24	0.076 (2)	0.0504 (19)	0.0365 (15)	−0.0062 (17)	0.0066 (14)	−0.0028 (13)
C25	0.074 (2)	0.0473 (19)	0.0487 (16)	0.0012 (17)	0.0202 (15)	−0.0021 (14)
C26	0.115 (3)	0.063 (3)	0.101 (3)	0.010 (2)	0.041 (2)	−0.004 (2)
C27	0.0613 (18)	0.053 (2)	0.0509 (17)	−0.0127 (17)	0.0075 (14)	0.0059 (17)
C28	0.117 (3)	0.078 (2)	0.0457 (18)	−0.021 (2)	0.0045 (18)	0.0153 (17)

Geometric parameters (Å, º)

O1—C21	1.407 (3)	C12—H12B	0.970
O1—C13	1.455 (3)	C13—C16	1.509 (4)
O2—C21	1.403 (3)	C13—C14	1.512 (5)
O2—C25	1.444 (3)	C14—C15	1.264 (4)
O3—C24	1.437 (3)	C14—H14	0.930
O3—H3O	0.820	C15—H15A	0.930
O4—C23	1.429 (3)	C15—H15B	0.930
O4—H4O	0.820	C16—H16A	0.960
O5—C27	1.335 (4)	C16—H16B	0.960
O5—C22	1.454 (3)	C16—H16C	0.960
O6—C27	1.198 (4)	C17—H17A	0.960
C1—C10	1.328 (4)	C17—H17B	0.960
C1—C2	1.493 (4)	C17—H17C	0.960
C1—H1	0.943 (10)	C18—H18A	0.960
C2—C3	1.526 (4)	C18—H18B	0.960
C2—H2A	0.970	C18—H18C	0.960
C2—H2B	0.970	C19—H19A	0.960
C3—C4	1.532 (4)	C19—H19B	0.960
C3—H3A	0.970	C19—H19C	0.960
C3—H3B	0.970	C20—H20A	0.960
C4—C19	1.533 (4)	C20—H20B	0.960
C4—C18	1.538 (4)	C20—H20C	0.960
C4—C5	1.542 (4)	C21—C22	1.521 (4)
C5—C10	1.517 (3)	C21—H21	0.980
C5—C6	1.526 (4)	C22—C23	1.503 (4)
C5—H5	0.980	C22—H22	0.980
C6—C7	1.526 (4)	C23—C24	1.503 (4)
C6—H6A	0.970	C23—H23	0.980
C6—H6B	0.970	C24—C25	1.519 (4)
C7—C8	1.537 (4)	C24—H24	0.980
C7—H7A	0.970	C25—C26	1.510 (4)
C7—H7B	0.970	C25—H25	0.980
C8—C17	1.534 (3)	C26—H26A	0.960
C8—C9	1.561 (4)	C26—H26B	0.960
C8—H8	0.980	C26—H26C	0.960
C9—C10	1.521 (4)	C27—C28	1.492 (4)
C9—C20	1.532 (3)	C28—H28A	0.960
C9—C11	1.550 (3)	C28—H28B	0.960
C11—C12	1.525 (4)	C28—H28C	0.960
C11—H11A	0.970	C28—H28D	0.960
C11—H11B	0.970	C28—H28E	0.960
C12—C13	1.538 (3)	C28—H28F	0.960
C12—H12A	0.970
C21—O1—C13	119.29 (19)	H15A—C15—H15B	120.0
C21—O2—C25	114.0 (2)	C13—C16—H16A	109.5
C24—O3—H3O	109.5	C13—C16—H16B	109.5
C23—O4—H4O	109.5	H16A—C16—H16B	109.5
C27—O5—C22	117.9 (2)	C13—C16—H16C	109.5
C10—C1—C2	125.4 (3)	H16A—C16—H16C	109.5
C10—C1—H1	117.6 (17)	H16B—C16—H16C	109.5
C2—C1—H1	117.0 (17)	C8—C17—H17A	109.5
C1—C2—C3	111.5 (3)	C8—C17—H17B	109.5
C1—C2—H2A	109.3	H17A—C17—H17B	109.5
C3—C2—H2A	109.3	C8—C17—H17C	109.5
C1—C2—H2B	109.3	H17A—C17—H17C	109.5
C3—C2—H2B	109.3	H17B—C17—H17C	109.5
H2A—C2—H2B	108.0	C4—C18—H18A	109.5
C2—C3—C4	112.0 (2)	C4—C18—H18B	109.5
C2—C3—H3A	109.2	H18A—C18—H18B	109.5
C4—C3—H3A	109.2	C4—C18—H18C	109.5
C2—C3—H3B	109.2	H18A—C18—H18C	109.5
C4—C3—H3B	109.2	H18B—C18—H18C	109.5
H3A—C3—H3B	107.9	C4—C19—H19A	109.5
C3—C4—C19	109.7 (3)	C4—C19—H19B	109.5
C3—C4—C18	109.8 (2)	H19A—C19—H19B	109.5
C19—C4—C18	108.2 (3)	C4—C19—H19C	109.5
C3—C4—C5	109.0 (2)	H19A—C19—H19C	109.5
C19—C4—C5	108.8 (2)	H19B—C19—H19C	109.5
C18—C4—C5	111.2 (3)	C9—C20—H20A	109.5
C10—C5—C6	107.7 (2)	C9—C20—H20B	109.5
C10—C5—C4	113.3 (2)	H20A—C20—H20B	109.5
C6—C5—C4	116.2 (2)	C9—C20—H20C	109.5
C10—C5—H5	106.3	H20A—C20—H20C	109.5
C6—C5—H5	106.3	H20B—C20—H20C	109.5
C4—C5—H5	106.3	O2—C21—O1	112.7 (2)
C5—C6—C7	111.7 (2)	O2—C21—C22	111.7 (2)
C5—C6—H6A	109.3	O1—C21—C22	105.1 (2)
C7—C6—H6A	109.3	O2—C21—H21	109.1
C5—C6—H6B	109.3	O1—C21—H21	109.1
C7—C6—H6B	109.3	C22—C21—H21	109.1
H6A—C6—H6B	107.9	O5—C22—C23	108.7 (2)
C6—C7—C8	113.9 (2)	O5—C22—C21	107.5 (2)
C6—C7—H7A	108.8	C23—C22—C21	109.8 (2)
C8—C7—H7A	108.8	O5—C22—H22	110.3
C6—C7—H7B	108.8	C23—C22—H22	110.3
C8—C7—H7B	108.8	C21—C22—H22	110.3
H7A—C7—H7B	107.7	O4—C23—C24	112.2 (2)
C17—C8—C7	109.7 (2)	O4—C23—C22	109.2 (2)
C17—C8—C9	113.0 (2)	C24—C23—C22	112.7 (2)
C7—C8—C9	112.1 (2)	O4—C23—H23	107.5
C17—C8—H8	107.3	C24—C23—H23	107.5
C7—C8—H8	107.3	C22—C23—H23	107.5
C9—C8—H8	107.3	O3—C24—C23	106.6 (2)
C10—C9—C20	113.3 (2)	O3—C24—C25	110.0 (2)
C10—C9—C11	111.2 (2)	C23—C24—C25	110.3 (2)
C20—C9—C11	106.71 (19)	O3—C24—H24	110.0
C10—C9—C8	107.55 (19)	C23—C24—H24	110.0
C20—C9—C8	110.3 (2)	C25—C24—H24	110.0
C11—C9—C8	107.6 (2)	O2—C25—C26	107.2 (2)
C1—C10—C5	121.2 (3)	O2—C25—C24	109.2 (2)
C1—C10—C9	124.0 (2)	C26—C25—C24	113.5 (3)
C5—C10—C9	114.5 (2)	O2—C25—H25	108.9
C12—C11—C9	115.3 (2)	C26—C25—H25	108.9
C12—C11—H11A	108.4	C24—C25—H25	108.9
C9—C11—H11A	108.4	C25—C26—H26A	109.5
C12—C11—H11B	108.4	C25—C26—H26B	109.5
C9—C11—H11B	108.4	H26A—C26—H26B	109.5
H11A—C11—H11B	107.5	C25—C26—H26C	109.5
C11—C12—C13	114.0 (2)	H26A—C26—H26C	109.5
C11—C12—H12A	108.8	H26B—C26—H26C	109.5
C13—C12—H12A	108.8	O6—C27—O5	123.1 (3)
C11—C12—H12B	108.8	O6—C27—C28	124.7 (3)
C13—C12—H12B	108.8	O5—C27—C28	112.2 (3)
H12A—C12—H12B	107.7	C27—C28—H28A	109.5
O1—C13—C16	111.7 (3)	C27—C28—H28B	109.5
O1—C13—C14	106.4 (2)	H28A—C28—H28B	109.5
C16—C13—C14	114.3 (3)	C27—C28—H28C	109.5
O1—C13—C12	102.89 (18)	H28A—C28—H28C	109.5
C16—C13—C12	111.7 (2)	H28B—C28—H28C	109.5
C14—C13—C12	109.3 (3)	C27—C28—H28D	109.5
C15—C14—C13	128.8 (5)	C27—C28—H28E	109.5
C15—C14—H14	115.6	H28D—C28—H28E	109.5
C13—C14—H14	115.6	C27—C28—H28F	109.5
C14—C15—H15A	120.0	H28D—C28—H28F	109.5
C14—C15—H15B	120.0	H28E—C28—H28F	109.5
C10—C1—C2—C3	15.5 (4)	C9—C11—C12—C13	−159.8 (2)
C1—C2—C3—C4	−44.8 (4)	C21—O1—C13—C16	−58.1 (3)
C2—C3—C4—C19	−58.7 (3)	C21—O1—C13—C14	67.1 (3)
C2—C3—C4—C18	−177.5 (3)	C21—O1—C13—C12	−178.0 (2)
C2—C3—C4—C5	60.4 (3)	C11—C12—C13—O1	57.1 (3)
C3—C4—C5—C10	−45.6 (3)	C11—C12—C13—C16	−62.8 (3)
C19—C4—C5—C10	74.0 (3)	C11—C12—C13—C14	169.8 (3)
C18—C4—C5—C10	−166.8 (2)	O1—C13—C14—C15	−134.1 (4)
C3—C4—C5—C6	79.9 (3)	C16—C13—C14—C15	−10.4 (5)
C19—C4—C5—C6	−160.4 (2)	C12—C13—C14—C15	115.5 (4)
C18—C4—C5—C6	−41.3 (3)	C25—O2—C21—O1	58.4 (3)
C10—C5—C6—C7	−55.5 (3)	C25—O2—C21—C22	−59.6 (3)
C4—C5—C6—C7	176.2 (2)	C13—O1—C21—O2	81.0 (3)
C5—C6—C7—C8	52.5 (3)	C13—O1—C21—C22	−157.2 (2)
C6—C7—C8—C17	76.1 (3)	C27—O5—C22—C23	134.6 (3)
C6—C7—C8—C9	−50.3 (3)	C27—O5—C22—C21	−106.6 (3)
C17—C8—C9—C10	−73.3 (3)	O2—C21—C22—O5	−65.2 (3)
C7—C8—C9—C10	51.3 (3)	O1—C21—C22—O5	172.3 (2)
C17—C8—C9—C20	50.8 (3)	O2—C21—C22—C23	52.9 (3)
C7—C8—C9—C20	175.4 (2)	O1—C21—C22—C23	−69.6 (3)
C17—C8—C9—C11	166.8 (2)	O5—C22—C23—O4	−58.7 (3)
C7—C8—C9—C11	−68.6 (3)	C21—C22—C23—O4	−176.1 (2)
C2—C1—C10—C5	−2.1 (4)	O5—C22—C23—C24	66.8 (3)
C2—C1—C10—C9	−175.7 (3)	C21—C22—C23—C24	−50.6 (3)
C6—C5—C10—C1	−112.2 (3)	O4—C23—C24—O3	−64.0 (3)
C4—C5—C10—C1	17.8 (3)	C22—C23—C24—O3	172.2 (2)
C6—C5—C10—C9	62.0 (3)	O4—C23—C24—C25	176.6 (2)
C4—C5—C10—C9	−168.0 (2)	C22—C23—C24—C25	52.8 (3)
C20—C9—C10—C1	−7.7 (4)	C21—O2—C25—C26	−176.4 (2)
C11—C9—C10—C1	−127.9 (3)	C21—O2—C25—C24	60.2 (3)
C8—C9—C10—C1	114.5 (3)	O3—C24—C25—O2	−172.3 (2)
C20—C9—C10—C5	178.3 (2)	C23—C24—C25—O2	−55.0 (3)
C11—C9—C10—C5	58.1 (3)	O3—C24—C25—C26	68.1 (3)
C8—C9—C10—C5	−59.5 (3)	C23—C24—C25—C26	−174.5 (2)
C10—C9—C11—C12	51.7 (3)	C22—O5—C27—O6	−0.6 (4)
C20—C9—C11—C12	−72.4 (3)	C22—O5—C27—C28	179.6 (2)
C8—C9—C11—C12	169.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O4^i	0.82	1.91	2.714 (3)	165
O4—H4O···O6^i	0.82	2.17	2.968 (3)	163

Symmetry code: (i) −x, y−1/2, −z+1.