An ent-kaurane diterpenoid from Isodon japonica

The title compound, 1β,7β-dihydr­oxy-6β,15β-diacet­oxy-16α,17:7α,20-diep­oxy-ent-kaurane or Maoyecrystal B, C₂₄H₃₄O₈·H₂O, crystallizes with one mol­ecule of water of crystallization. It is a natural diterpenoid composed of four fused rings with the expected cis and trans junctions. Mol­ecules are linked together by O—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.039
• wR factor = 0.087
• Data-to-parameter ratio = 9.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT731_ALERT_1_B Bond    Calc     0.83(5), Rep   0.822(10) ......       5.00 su-Rat
              O9   -H0B     1.555   1.555
PLAT735_ALERT_1_B D-H     Calc     0.83(5), Rep   0.822(10) ......       5.00 su-Rat
              O9   -H2#     1.555   1.555

Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.68 mm
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.58 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C4     -   C19     ..       5.64 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O8
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

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           27.50
           From the CIF: _reflns_number_total               3003
           Count of symmetry unique reflns         3003
           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
   7 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   3 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
   3 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, 1997b); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL.

1β,7β-dihydroxy-6β,15β-diacetoxy-16α,17:7α,20-diepoxy-ent-kaurane

Crystal data

C24H34O8·H2O	Dx = 1.345 Mg m^−3
Mr = 468.53	Melting point: 474 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
a = 9.492 (2) Å	Cell parameters from 28 reflections
b = 14.909 (4) Å	θ = 2.8–13.6°
c = 16.354 (4) Å	µ = 0.10 mm^−1
V = 2314.2 (8) Å^3	T = 294 K
Z = 4	Prism, colourless
F(000) = 1008	0.68 × 0.68 × 0.44 mm

Data collection

Siemens P4 diffractometer	Rint = 0.015
Radiation source: normal-focus sealed tube	θmax = 27.5°, θmin = 1.9°
Graphite monochromator	h = 0→12
ω scans	k = 0→19
3354 measured reflections	l = −1→21
3003 independent reflections	3 standard reflections every 97 reflections
2210 reflections with I > 2σ(I)	intensity decay: 2.4%

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)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.087	w = 1/[σ^2(Fo^2) + (0.0466P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.96	(Δ/σ)max < 0.001
3003 reflections	Δρmax = 0.20 e Å^−3
311 parameters	Δρmin = −0.15 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: 0.0094 (10)

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	1.01900 (15)	0.38744 (11)	0.28115 (10)	0.0338 (4)
O2	0.72314 (18)	0.17258 (11)	0.42276 (12)	0.0400 (4)
H2O	0.7375	0.1184	0.4257	0.048*
O3	0.65670 (16)	0.46964 (10)	0.27049 (10)	0.0323 (4)
O4	0.7510 (2)	0.60440 (12)	0.24395 (15)	0.0620 (6)
O5	0.91558 (19)	0.46033 (11)	0.17605 (10)	0.0358 (4)
H5O	0.9000	0.5116	0.1917	0.043*
O6	0.58035 (15)	0.30260 (11)	0.19630 (11)	0.0314 (4)
O7	0.45387 (19)	0.39210 (13)	0.11464 (13)	0.0504 (5)
O8	0.6939 (3)	0.25681 (18)	0.00405 (13)	0.0709 (7)
C1	0.8541 (3)	0.21942 (16)	0.42762 (15)	0.0327 (6)
H1	0.9313	0.1761	0.4225	0.039*
C2	0.8628 (3)	0.2641 (2)	0.51088 (16)	0.0423 (7)
H2A	0.8536	0.2191	0.5534	0.051*
H2B	0.9540	0.2927	0.5170	0.051*
C3	0.7475 (3)	0.33332 (18)	0.52026 (15)	0.0424 (7)
H3A	0.7513	0.3578	0.5752	0.051*
H3B	0.6569	0.3041	0.5136	0.051*
C4	0.7587 (3)	0.41029 (17)	0.45865 (15)	0.0376 (6)
C5	0.7628 (2)	0.36849 (14)	0.37094 (13)	0.0269 (5)
H5	0.6676	0.3458	0.3606	0.032*
C6	0.7908 (2)	0.43839 (15)	0.30430 (15)	0.0269 (5)
H6	0.8384	0.4897	0.3296	0.032*
C7	0.8873 (2)	0.40011 (16)	0.23929 (15)	0.0285 (5)
C8	0.8400 (2)	0.31033 (16)	0.20316 (14)	0.0264 (5)
C9	0.8196 (2)	0.24230 (14)	0.27517 (13)	0.0259 (5)
H9	0.7183	0.2302	0.2791	0.031*
C10	0.8637 (2)	0.28744 (15)	0.35664 (14)	0.0265 (5)
C11	0.8913 (3)	0.15257 (17)	0.25601 (16)	0.0375 (6)
H11A	0.9924	0.1592	0.2623	0.045*
H11B	0.8596	0.1078	0.2949	0.045*
C12	0.8594 (3)	0.12003 (16)	0.16961 (15)	0.0404 (7)
H12A	0.7654	0.0946	0.1685	0.048*
H12B	0.9253	0.0728	0.1554	0.048*
C13	0.8690 (3)	0.19507 (17)	0.10519 (15)	0.0378 (6)
H13	0.9137	0.1736	0.0549	0.045*
C14	0.9479 (3)	0.27467 (17)	0.14063 (16)	0.0378 (6)
H14A	0.9689	0.3190	0.0990	0.045*
H14B	1.0347	0.2562	0.1670	0.045*
C15	0.7072 (2)	0.31427 (16)	0.14824 (14)	0.0291 (5)
H15	0.7039	0.3715	0.1189	0.035*
C16	0.7271 (3)	0.23696 (17)	0.08781 (15)	0.0404 (6)
C17	0.6113 (4)	0.1918 (2)	0.0475 (2)	0.0668 (10)
H17A	0.6235	0.1291	0.0333	0.080*
H17B	0.5163	0.2085	0.0632	0.080*
C18	0.6263 (4)	0.4687 (2)	0.46492 (18)	0.0568 (9)
H18A	0.5450	0.4335	0.4512	0.068*
H18B	0.6340	0.5183	0.4277	0.068*
H18C	0.6171	0.4909	0.5198	0.068*
C19	0.8852 (4)	0.4697 (2)	0.48101 (18)	0.0590 (9)
H19A	0.8761	0.4896	0.5366	0.071*
H19B	0.8879	0.5208	0.4453	0.071*
H19C	0.9706	0.4359	0.4751	0.071*
C20	1.0148 (2)	0.32072 (17)	0.34482 (15)	0.0336 (6)
H20A	1.0494	0.3463	0.3955	0.040*
H20B	1.0753	0.2708	0.3303	0.040*
C21	0.6501 (3)	0.55592 (17)	0.24686 (17)	0.0397 (6)
C22	0.5048 (3)	0.5832 (2)	0.2239 (2)	0.0582 (9)
H22A	0.4420	0.5333	0.2310	0.070*	0.50
H22B	0.5035	0.6019	0.1677	0.070*	0.50
H22C	0.4750	0.6320	0.2581	0.070*	0.50
H22D	0.5050	0.6448	0.2069	0.070*	0.50
H22E	0.4436	0.5762	0.2702	0.070*	0.50
H22F	0.4720	0.5461	0.1798	0.070*	0.50
C23	0.4636 (3)	0.34688 (17)	0.17536 (17)	0.0356 (6)
C24	0.3508 (3)	0.3321 (2)	0.2364 (2)	0.0661 (10)
H24A	0.3852	0.2938	0.2791	0.079*	0.50
H24B	0.2713	0.3044	0.2104	0.079*	0.50
H24C	0.3228	0.3887	0.2593	0.079*	0.50
H24D	0.2677	0.3641	0.2201	0.079*	0.50
H24E	0.3815	0.3535	0.2888	0.079*	0.50
H24F	0.3301	0.2692	0.2399	0.079*	0.50
O9	0.1993 (3)	0.48854 (15)	0.08138 (19)	0.0666 (7)
H0A	0.271 (2)	0.459 (2)	0.091 (2)	0.089 (13)*
H0B	0.128 (4)	0.465 (4)	0.101 (4)	0.20 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0186 (8)	0.0377 (9)	0.0450 (10)	−0.0049 (7)	0.0000 (8)	0.0027 (8)
O2	0.0327 (9)	0.0357 (9)	0.0516 (11)	−0.0061 (8)	−0.0008 (9)	0.0069 (9)
O3	0.0256 (8)	0.0277 (8)	0.0435 (10)	0.0047 (7)	0.0000 (8)	−0.0011 (8)
O4	0.0460 (12)	0.0359 (10)	0.1041 (17)	−0.0013 (10)	0.0000 (13)	0.0180 (12)
O5	0.0360 (9)	0.0309 (9)	0.0405 (10)	−0.0027 (8)	0.0087 (9)	0.0034 (8)
O6	0.0223 (8)	0.0329 (9)	0.0391 (10)	0.0020 (7)	−0.0009 (7)	0.0045 (8)
O7	0.0369 (10)	0.0555 (12)	0.0589 (12)	0.0092 (10)	−0.0060 (10)	0.0183 (11)
O8	0.1008 (19)	0.0765 (14)	0.0353 (10)	0.0229 (16)	−0.0176 (14)	−0.0085 (11)
C1	0.0245 (12)	0.0377 (13)	0.0360 (14)	0.0014 (11)	−0.0007 (11)	0.0040 (11)
C2	0.0394 (15)	0.0541 (17)	0.0334 (14)	−0.0047 (14)	−0.0014 (13)	0.0078 (13)
C3	0.0434 (16)	0.0514 (16)	0.0324 (14)	−0.0066 (14)	0.0068 (12)	−0.0050 (12)
C4	0.0397 (15)	0.0399 (14)	0.0333 (13)	−0.0055 (13)	0.0051 (12)	−0.0095 (12)
C5	0.0213 (11)	0.0306 (11)	0.0289 (12)	−0.0012 (10)	0.0028 (10)	−0.0055 (10)
C6	0.0225 (11)	0.0233 (11)	0.0348 (13)	−0.0005 (10)	−0.0011 (10)	−0.0040 (10)
C7	0.0224 (11)	0.0297 (12)	0.0334 (13)	−0.0033 (10)	0.0024 (11)	0.0053 (11)
C8	0.0195 (10)	0.0315 (12)	0.0284 (12)	0.0030 (10)	0.0036 (10)	0.0015 (11)
C9	0.0206 (11)	0.0235 (11)	0.0335 (12)	0.0043 (9)	−0.0022 (10)	0.0001 (10)
C10	0.0201 (11)	0.0306 (12)	0.0289 (12)	0.0006 (10)	−0.0009 (10)	0.0002 (10)
C11	0.0386 (14)	0.0304 (12)	0.0436 (15)	0.0115 (11)	−0.0034 (13)	0.0003 (12)
C12	0.0434 (15)	0.0317 (13)	0.0460 (16)	0.0129 (13)	0.0034 (14)	−0.0071 (12)
C13	0.0405 (15)	0.0397 (14)	0.0331 (14)	0.0072 (13)	0.0084 (12)	−0.0095 (12)
C14	0.0329 (14)	0.0413 (14)	0.0392 (15)	0.0022 (13)	0.0115 (12)	−0.0006 (13)
C15	0.0257 (11)	0.0310 (12)	0.0305 (13)	−0.0003 (11)	0.0000 (10)	0.0018 (11)
C16	0.0453 (16)	0.0421 (14)	0.0337 (14)	0.0073 (14)	−0.0035 (13)	−0.0056 (12)
C17	0.067 (2)	0.062 (2)	0.071 (2)	0.010 (2)	−0.0282 (19)	−0.030 (2)
C18	0.073 (2)	0.0526 (18)	0.0446 (17)	0.0174 (18)	0.0162 (17)	−0.0098 (16)
C19	0.080 (2)	0.0546 (19)	0.0426 (18)	−0.0210 (18)	0.0019 (17)	−0.0144 (16)
C20	0.0222 (11)	0.0440 (14)	0.0347 (14)	0.0006 (12)	0.0004 (11)	0.0020 (12)
C21	0.0429 (15)	0.0309 (13)	0.0452 (15)	0.0092 (13)	0.0013 (14)	−0.0027 (12)
C22	0.0471 (16)	0.0411 (15)	0.086 (3)	0.0154 (14)	−0.0105 (19)	0.0013 (17)
C23	0.0244 (12)	0.0317 (13)	0.0508 (16)	−0.0022 (11)	−0.0046 (12)	0.0019 (14)
C24	0.0308 (15)	0.071 (2)	0.097 (3)	0.0076 (16)	0.0121 (18)	0.030 (2)
O9	0.0542 (15)	0.0402 (11)	0.105 (2)	0.0110 (12)	−0.0139 (16)	−0.0032 (13)

Geometric parameters (Å, º)

O1—C7	1.438 (3)	C11—H11A	0.9700
O1—C20	1.441 (3)	C11—H11B	0.9700
O2—C1	1.428 (3)	C12—C13	1.539 (3)
O2—H2O	0.8200	C12—H12A	0.9700
O3—C21	1.345 (3)	C12—H12B	0.9700
O3—C6	1.464 (3)	C13—C16	1.511 (4)
O4—C21	1.201 (3)	C13—C14	1.518 (4)
O5—C7	1.396 (3)	C13—H13	0.9800
O5—H5O	0.8200	C14—H14A	0.9700
O6—C23	1.334 (3)	C14—H14B	0.9700
O6—C15	1.449 (3)	C15—C16	1.530 (3)
O7—C23	1.204 (3)	C15—H15	0.9800
O8—C17	1.435 (4)	C16—C17	1.448 (4)
O8—C16	1.437 (3)	C17—H17A	0.9700
C1—C2	1.518 (4)	C17—H17B	0.9700
C1—C10	1.544 (3)	C18—H18A	0.9600
C1—H1	0.9800	C18—H18B	0.9600
C2—C3	1.512 (4)	C18—H18C	0.9600
C2—H2A	0.9700	C19—H19A	0.9600
C2—H2B	0.9700	C19—H19B	0.9600
C3—C4	1.531 (4)	C19—H19C	0.9600
C3—H3A	0.9700	C20—H20A	0.9700
C3—H3B	0.9700	C20—H20B	0.9700
C4—C18	1.532 (4)	C21—C22	1.486 (4)
C4—C19	1.536 (4)	C22—H22A	0.9600
C4—C5	1.564 (3)	C22—H22B	0.9600
C5—C6	1.531 (3)	C22—H22C	0.9600
C5—C10	1.559 (3)	C22—H22D	0.9600
C5—H5	0.9800	C22—H22E	0.9600
C6—C7	1.515 (3)	C22—H22F	0.9600
C6—H6	0.9800	C23—C24	1.481 (4)
C7—C8	1.531 (3)	C24—H24A	0.9600
C8—C14	1.542 (3)	C24—H24B	0.9600
C8—C15	1.549 (3)	C24—H24C	0.9600
C8—C9	1.566 (3)	C24—H24D	0.9600
C9—C11	1.533 (3)	C24—H24E	0.9600
C9—C10	1.550 (3)	C24—H24F	0.9600
C9—H9	0.9800	O9—H0A	0.827 (10)
C10—C20	1.530 (3)	O9—H0B	0.822 (10)
C11—C12	1.524 (3)
C7—O1—C20	114.27 (16)	C8—C14—H14B	111.5
C1—O2—H2O	109.5	H14A—C14—H14B	109.3
C21—O3—C6	116.97 (19)	O6—C15—C16	111.27 (19)
C7—O5—H5O	109.5	O6—C15—C8	110.93 (17)
C23—O6—C15	119.44 (18)	C16—C15—C8	104.21 (19)
C17—O8—C16	60.56 (19)	O6—C15—H15	110.1
O2—C1—C2	108.2 (2)	C16—C15—H15	110.1
O2—C1—C10	109.30 (19)	C8—C15—H15	110.1
C2—C1—C10	112.5 (2)	O8—C16—C17	59.67 (19)
O2—C1—H1	108.9	O8—C16—C13	117.4 (2)
C2—C1—H1	108.9	C17—C16—C13	124.8 (2)
C10—C1—H1	108.9	O8—C16—C15	115.7 (2)
C3—C2—C1	110.6 (2)	C17—C16—C15	123.4 (2)
C3—C2—H2A	109.5	C13—C16—C15	107.5 (2)
C1—C2—H2A	109.5	O8—C17—C16	59.8 (2)
C3—C2—H2B	109.5	O8—C17—H17A	117.8
C1—C2—H2B	109.5	C16—C17—H17A	117.8
H2A—C2—H2B	108.1	O8—C17—H17B	117.8
C2—C3—C4	113.3 (2)	C16—C17—H17B	117.8
C2—C3—H3A	108.9	H17A—C17—H17B	114.9
C4—C3—H3A	108.9	C4—C18—H18A	109.5
C2—C3—H3B	108.9	C4—C18—H18B	109.5
C4—C3—H3B	108.9	H18A—C18—H18B	109.5
H3A—C3—H3B	107.7	C4—C18—H18C	109.5
C3—C4—C18	109.0 (2)	H18A—C18—H18C	109.5
C3—C4—C19	109.3 (2)	H18B—C18—H18C	109.5
C18—C4—C19	107.3 (2)	C4—C19—H19A	109.5
C3—C4—C5	107.85 (19)	C4—C19—H19B	109.5
C18—C4—C5	108.0 (2)	H19A—C19—H19B	109.5
C19—C4—C5	115.4 (2)	C4—C19—H19C	109.5
C6—C5—C10	108.31 (18)	H19A—C19—H19C	109.5
C6—C5—C4	112.70 (18)	H19B—C19—H19C	109.5
C10—C5—C4	117.5 (2)	O1—C20—C10	109.94 (18)
C6—C5—H5	105.8	O1—C20—H20A	109.7
C10—C5—H5	105.8	C10—C20—H20A	109.7
C4—C5—H5	105.8	O1—C20—H20B	109.7
O3—C6—C7	112.38 (19)	C10—C20—H20B	109.7
O3—C6—C5	109.56 (17)	H20A—C20—H20B	108.2
C7—C6—C5	110.36 (18)	O4—C21—O3	123.4 (2)
O3—C6—H6	108.1	O4—C21—C22	124.4 (2)
C7—C6—H6	108.1	O3—C21—C22	112.2 (2)
C5—C6—H6	108.1	C21—C22—H22A	109.5
O5—C7—O1	105.68 (17)	C21—C22—H22B	109.5
O5—C7—C6	113.20 (19)	H22A—C22—H22B	109.5
O1—C7—C6	103.96 (18)	C21—C22—H22C	109.5
O5—C7—C8	109.45 (19)	H22A—C22—H22C	109.5
O1—C7—C8	108.91 (18)	H22B—C22—H22C	109.5
C6—C7—C8	115.01 (18)	C21—C22—H22D	109.5
C7—C8—C14	111.27 (19)	H22A—C22—H22D	141.1
C7—C8—C15	115.44 (18)	H22B—C22—H22D	56.3
C14—C8—C15	99.72 (19)	H22C—C22—H22D	56.3
C7—C8—C9	108.20 (18)	C21—C22—H22E	109.5
C14—C8—C9	110.94 (18)	H22A—C22—H22E	56.3
C15—C8—C9	111.11 (18)	H22B—C22—H22E	141.1
C11—C9—C10	115.75 (19)	H22C—C22—H22E	56.3
C11—C9—C8	110.88 (19)	H22D—C22—H22E	109.5
C10—C9—C8	109.38 (17)	C21—C22—H22F	109.5
C11—C9—H9	106.8	H22A—C22—H22F	56.3
C10—C9—H9	106.8	H22B—C22—H22F	56.3
C8—C9—H9	106.8	H22C—C22—H22F	141.1
C20—C10—C1	111.30 (19)	H22D—C22—H22F	109.5
C20—C10—C9	106.58 (19)	H22E—C22—H22F	109.5
C1—C10—C9	110.19 (18)	O7—C23—O6	123.6 (2)
C20—C10—C5	110.08 (19)	O7—C23—C24	125.7 (2)
C1—C10—C5	111.10 (18)	O6—C23—C24	110.7 (2)
C9—C10—C5	107.42 (17)	C23—C24—H24A	109.5
C12—C11—C9	112.3 (2)	C23—C24—H24B	109.5
C12—C11—H11A	109.2	H24A—C24—H24B	109.5
C9—C11—H11A	109.2	C23—C24—H24C	109.5
C12—C11—H11B	109.2	H24A—C24—H24C	109.5
C9—C11—H11B	109.2	H24B—C24—H24C	109.5
H11A—C11—H11B	107.9	C23—C24—H24D	109.5
C11—C12—C13	113.0 (2)	H24A—C24—H24D	141.1
C11—C12—H12A	109.0	H24B—C24—H24D	56.3
C13—C12—H12A	109.0	H24C—C24—H24D	56.3
C11—C12—H12B	109.0	C23—C24—H24E	109.5
C13—C12—H12B	109.0	H24A—C24—H24E	56.3
H12A—C12—H12B	107.8	H24B—C24—H24E	141.1
C16—C13—C14	100.84 (19)	H24C—C24—H24E	56.3
C16—C13—C12	112.1 (2)	H24D—C24—H24E	109.5
C14—C13—C12	109.6 (2)	C23—C24—H24F	109.5
C16—C13—H13	111.3	H24A—C24—H24F	56.3
C14—C13—H13	111.3	H24B—C24—H24F	56.3
C12—C13—H13	111.3	H24C—C24—H24F	141.1
C13—C14—C8	101.26 (19)	H24D—C24—H24F	109.5
C13—C14—H14A	111.5	H24E—C24—H24F	109.5
C8—C14—H14A	111.5	H0A—O9—H0B	112 (4)
C13—C14—H14B	111.5
O2—C1—C2—C3	−63.3 (3)	C8—C9—C10—C1	−176.12 (18)
C10—C1—C2—C3	57.6 (3)	C11—C9—C10—C5	−171.2 (2)
C1—C2—C3—C4	−62.6 (3)	C8—C9—C10—C5	62.7 (2)
C2—C3—C4—C18	171.8 (2)	C6—C5—C10—C20	49.3 (2)
C2—C3—C4—C19	−71.3 (3)	C4—C5—C10—C20	−79.7 (2)
C2—C3—C4—C5	54.8 (3)	C6—C5—C10—C1	173.08 (18)
C3—C4—C5—C6	−173.5 (2)	C4—C5—C10—C1	44.0 (3)
C18—C4—C5—C6	68.9 (3)	C6—C5—C10—C9	−66.3 (2)
C19—C4—C5—C6	−51.1 (3)	C4—C5—C10—C9	164.59 (19)
C3—C4—C5—C10	−46.5 (3)	C10—C9—C11—C12	−171.3 (2)
C18—C4—C5—C10	−164.1 (2)	C8—C9—C11—C12	−45.9 (3)
C19—C4—C5—C10	75.9 (3)	C9—C11—C12—C13	43.7 (3)
C21—O3—C6—C7	−91.0 (2)	C11—C12—C13—C16	−94.9 (3)
C21—O3—C6—C5	146.0 (2)	C11—C12—C13—C14	16.2 (3)
C10—C5—C6—O3	133.77 (18)	C16—C13—C14—C8	47.9 (2)
C4—C5—C6—O3	−94.5 (2)	C12—C13—C14—C8	−70.5 (2)
C10—C5—C6—C7	9.5 (2)	C7—C8—C14—C13	−171.94 (19)
C4—C5—C6—C7	141.2 (2)	C15—C8—C14—C13	−49.6 (2)
C20—O1—C7—O5	−174.78 (17)	C9—C8—C14—C13	67.5 (2)
C20—O1—C7—C6	65.8 (2)	C23—O6—C15—C16	−99.3 (2)
C20—O1—C7—C8	−57.3 (2)	C23—O6—C15—C8	145.2 (2)
O3—C6—C7—O5	56.6 (2)	C7—C8—C15—O6	−89.1 (2)
C5—C6—C7—O5	179.24 (18)	C14—C8—C15—O6	151.66 (18)
O3—C6—C7—O1	170.80 (16)	C9—C8—C15—O6	34.6 (2)
C5—C6—C7—O1	−66.6 (2)	C7—C8—C15—C16	151.1 (2)
O3—C6—C7—C8	−70.2 (2)	C14—C8—C15—C16	31.8 (2)
C5—C6—C7—C8	52.4 (3)	C9—C8—C15—C16	−85.2 (2)
O5—C7—C8—C14	53.9 (2)	C17—O8—C16—C13	116.2 (3)
O1—C7—C8—C14	−61.2 (2)	C17—O8—C16—C15	−115.2 (3)
C6—C7—C8—C14	−177.4 (2)	C14—C13—C16—O8	104.9 (3)
O5—C7—C8—C15	−58.8 (2)	C12—C13—C16—O8	−138.5 (2)
O1—C7—C8—C15	−173.91 (17)	C14—C13—C16—C17	175.5 (3)
C6—C7—C8—C15	69.9 (3)	C12—C13—C16—C17	−67.9 (4)
O5—C7—C8—C9	175.99 (17)	C14—C13—C16—C15	−27.5 (2)
O1—C7—C8—C9	60.9 (2)	C12—C13—C16—C15	89.0 (2)
C6—C7—C8—C9	−55.3 (2)	O6—C15—C16—O8	103.9 (3)
C7—C8—C9—C11	−132.55 (19)	C8—C15—C16—O8	−136.4 (2)
C14—C8—C9—C11	−10.2 (3)	O6—C15—C16—C17	34.7 (3)
C15—C8—C9—C11	99.7 (2)	C8—C15—C16—C17	154.3 (3)
C7—C8—C9—C10	−3.7 (2)	O6—C15—C16—C13	−122.7 (2)
C14—C8—C9—C10	118.6 (2)	C8—C15—C16—C13	−3.1 (2)
C15—C8—C9—C10	−131.42 (19)	C13—C16—C17—O8	−104.0 (3)
O2—C1—C10—C20	−164.56 (19)	C15—C16—C17—O8	102.5 (3)
C2—C1—C10—C20	75.3 (3)	C7—O1—C20—C10	−5.9 (3)
O2—C1—C10—C9	−46.5 (2)	C1—C10—C20—O1	−177.00 (17)
C2—C1—C10—C9	−166.7 (2)	C9—C10—C20—O1	62.8 (2)
O2—C1—C10—C5	72.4 (2)	C5—C10—C20—O1	−53.4 (2)
C2—C1—C10—C5	−47.8 (3)	C6—O3—C21—O4	8.3 (4)
C11—C9—C10—C20	70.9 (2)	C6—O3—C21—C22	−172.5 (2)
C8—C9—C10—C20	−55.2 (2)	C15—O6—C23—O7	5.4 (4)
C11—C9—C10—C1	−50.0 (3)	C15—O6—C23—C24	−174.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O9^i	0.82	2.03	2.842 (3)	170
O5—H5O···O4	0.82	2.15	2.879 (3)	147
O9—H0B···O5^ii	0.82 (1)	2.37 (3)	3.135 (3)	156 (6)
O9—H0A···O7	0.83 (1)	2.04 (1)	2.864 (3)	176 (4)

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