2β,24-Dihydroxy­urs-12-en-27-oic acid methanol solvate from the rhizome of Astilbe chinensis

The title compound, a novel triterpenoid, C₃₀H₄₈O₄·CH₄O, was isolated from the rhizome of Astilbe chinensis (Maxim.) Franch. et Sav. It contains five fused six-membered rings, which adopt half-chair conformations. In the crystal structure, inter­molecular O—H...O hydrogen bonds link the mol­ecules, forming an extensive network, which may be effective in the stabilization of the structure.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.044
• wR factor = 0.109
• Data-to-parameter ratio = 8.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
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           25.01
           From the CIF: _reflns_number_total               2764
           Count of symmetry unique reflns         2766
           Completeness (_total/calc)             99.93%
           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 C3     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C17    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C18    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C19    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C20    = .          S

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

  12 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
   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

---

Computing details

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

2 b,24-dihydroxyurs-12-en-27-oic acid methanol solvate

Crystal data

C30H48O4·CH4O	F(000) = 556
Mr = 504.73	Dx = 1.154 Mg m^−3
Monoclinic, P21	Melting point: 508 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 11.068 (3) Å	Cell parameters from 1996 reflections
b = 7.9037 (18) Å	θ = 2.9–22.8°
c = 16.677 (4) Å	µ = 0.08 mm^−1
β = 95.487 (4)°	T = 294 K
V = 1452.2 (6) Å^3	Plate, colorless
Z = 2	0.32 × 0.28 × 0.20 mm

Data collection

Bruker CCD area-detector diffractometer	2764 independent reflections
Radiation source: fine-focus sealed tube	2013 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.976, Tmax = 0.985	k = −9→6
7442 measured reflections	l = −19→15

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.110	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0617P)^2] where P = (Fo^2 + 2Fc^2)/3
2764 reflections	(Δ/σ)max = 0.002
336 parameters	Δρmax = 0.16 e Å^−3
1 restraint	Δρmin = −0.25 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	0.3451 (2)	0.4922 (5)	0.70011 (13)	0.0690 (8)
H1	0.4119	0.5275	0.7181	0.103*
O2	0.2393 (2)	0.1974 (4)	0.72067 (12)	0.0586 (7)
H2	0.2734	0.2827	0.7394	0.088*
O3	0.42138 (19)	0.3733 (3)	0.25983 (14)	0.0462 (6)
H3	0.4934	0.3743	0.2520	0.069*
O4	0.43757 (19)	0.1022 (3)	0.22756 (13)	0.0474 (6)
C1	0.2348 (3)	0.5833 (5)	0.48279 (19)	0.0461 (9)
H1A	0.3104	0.6092	0.4604	0.055*
H1B	0.1746	0.6646	0.4613	0.055*
C2	0.2534 (3)	0.6026 (5)	0.57458 (19)	0.0509 (10)
H2A	0.2833	0.7155	0.5877	0.061*
H2B	0.1759	0.5897	0.5965	0.061*
C3	0.3420 (3)	0.4742 (6)	0.61361 (19)	0.0521 (11)
H3A	0.4229	0.5013	0.5979	0.063*
C4	0.3143 (3)	0.2884 (5)	0.59109 (18)	0.0425 (9)
C5	0.2860 (3)	0.2758 (4)	0.49791 (18)	0.0358 (8)
H5	0.3631	0.3051	0.4770	0.043*
C6	0.2590 (3)	0.0968 (4)	0.46586 (18)	0.0418 (8)
H6A	0.3131	0.0169	0.4953	0.050*
H6B	0.1763	0.0663	0.4743	0.050*
C7	0.2757 (3)	0.0868 (4)	0.37686 (18)	0.0440 (9)
H7A	0.2589	−0.0279	0.3583	0.053*
H7B	0.3598	0.1114	0.3694	0.053*
C8	0.1930 (2)	0.2103 (4)	0.32449 (16)	0.0323 (7)
C9	0.2040 (3)	0.3906 (4)	0.36236 (16)	0.0335 (7)
H9	0.2866	0.4280	0.3549	0.040*
C10	0.1934 (3)	0.4047 (4)	0.45575 (17)	0.0340 (8)
C11	0.1206 (3)	0.5130 (5)	0.31231 (18)	0.0494 (9)
H11A	0.0375	0.4938	0.3240	0.059*
H11B	0.1422	0.6281	0.3280	0.059*
C12	0.1280 (3)	0.4941 (5)	0.22406 (18)	0.0417 (8)
H12	0.0920	0.5786	0.1911	0.050*
C13	0.1808 (3)	0.3689 (4)	0.18791 (17)	0.0322 (7)
C14	0.2347 (2)	0.2146 (4)	0.23480 (16)	0.0298 (7)
C15	0.1972 (3)	0.0496 (4)	0.18869 (18)	0.0354 (8)
H15A	0.2475	−0.0424	0.2114	0.043*
H15B	0.1137	0.0236	0.1971	0.043*
C16	0.2083 (3)	0.0580 (4)	0.09875 (18)	0.0396 (8)
H16A	0.1790	−0.0473	0.0741	0.048*
H16B	0.2933	0.0695	0.0899	0.048*
C17	0.1372 (3)	0.2053 (5)	0.05756 (17)	0.0372 (8)
C18	0.1866 (3)	0.3732 (4)	0.09621 (17)	0.0326 (7)
H18	0.1299	0.4618	0.0757	0.039*
C19	0.3134 (3)	0.4265 (4)	0.07159 (18)	0.0387 (8)
H19	0.3735	0.3451	0.0951	0.046*
C20	0.3156 (3)	0.4225 (5)	−0.02051 (19)	0.0443 (9)
H20	0.2575	0.5072	−0.0432	0.053*
C21	0.2749 (3)	0.2522 (5)	−0.05515 (19)	0.0512 (10)
H21A	0.2743	0.2557	−0.1133	0.061*
H21B	0.3325	0.1661	−0.0350	0.061*
C22	0.1498 (3)	0.2047 (6)	−0.03332 (18)	0.0481 (9)
H22A	0.1298	0.0927	−0.0544	0.058*
H22B	0.0912	0.2833	−0.0594	0.058*
C23	0.4281 (3)	0.1821 (7)	0.6166 (2)	0.0663 (13)
H23A	0.4911	0.2102	0.5831	0.099*
H23B	0.4087	0.0641	0.6107	0.099*
H23C	0.4554	0.2056	0.6718	0.099*
C24	0.2082 (3)	0.2197 (6)	0.63611 (17)	0.0467 (9)
H24A	0.1404	0.2975	0.6281	0.056*
H24B	0.1820	0.1119	0.6127	0.056*
C25	0.0624 (3)	0.3788 (5)	0.47933 (18)	0.0421 (8)
H25A	0.0531	0.4377	0.5287	0.063*
H25B	0.0478	0.2603	0.4865	0.063*
H25C	0.0054	0.4223	0.4374	0.063*
C26	0.0614 (3)	0.1458 (5)	0.32095 (19)	0.0511 (10)
H26A	0.0305	0.1638	0.3721	0.077*
H26B	0.0595	0.0271	0.3086	0.077*
H26C	0.0121	0.2062	0.2800	0.077*
C27	0.3744 (3)	0.2230 (5)	0.23998 (16)	0.0330 (7)
C28	0.0015 (3)	0.1904 (6)	0.0694 (2)	0.0528 (10)
H28A	−0.0274	0.0803	0.0525	0.079*
H28B	−0.0431	0.2754	0.0378	0.079*
H28C	−0.0097	0.2062	0.1253	0.079*
C29	0.3485 (3)	0.6020 (5)	0.1051 (2)	0.0567 (10)
H29A	0.4326	0.6230	0.0991	0.085*
H29B	0.3353	0.6067	0.1611	0.085*
H29C	0.2996	0.6863	0.0760	0.085*
C30	0.4400 (3)	0.4697 (6)	−0.0466 (2)	0.0615 (11)
H30A	0.5014	0.4018	−0.0176	0.092*
H30B	0.4559	0.5871	−0.0353	0.092*
H30C	0.4408	0.4498	−0.1033	0.092*
O5	0.6514 (3)	0.4051 (5)	0.2382 (2)	0.0821 (10)
H5A	0.6846	0.4946	0.2520	0.123*
C31	0.7162 (5)	0.3261 (6)	0.1804 (3)	0.0933 (16)
H31A	0.7423	0.4096	0.1440	0.140*
H31B	0.6648	0.2451	0.1509	0.140*
H31C	0.7857	0.2694	0.2068	0.140*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0553 (17)	0.111 (2)	0.0400 (14)	−0.0227 (18)	0.0007 (11)	−0.0191 (16)
O2	0.0690 (18)	0.075 (2)	0.0320 (13)	0.0065 (17)	0.0059 (11)	0.0045 (14)
O3	0.0319 (13)	0.0507 (16)	0.0566 (15)	−0.0049 (12)	0.0082 (11)	−0.0099 (13)
O4	0.0383 (13)	0.0525 (16)	0.0511 (14)	0.0181 (13)	0.0023 (10)	−0.0042 (13)
C1	0.054 (2)	0.045 (2)	0.042 (2)	−0.0046 (18)	0.0113 (15)	−0.0054 (18)
C2	0.056 (2)	0.054 (2)	0.044 (2)	−0.010 (2)	0.0121 (16)	−0.0143 (19)
C3	0.039 (2)	0.079 (3)	0.039 (2)	−0.019 (2)	0.0064 (15)	−0.015 (2)
C4	0.0321 (18)	0.064 (3)	0.0315 (18)	0.0049 (17)	0.0041 (14)	−0.0002 (17)
C5	0.0303 (17)	0.045 (2)	0.0330 (18)	0.0018 (15)	0.0075 (13)	0.0013 (16)
C6	0.051 (2)	0.041 (2)	0.0341 (18)	0.0101 (18)	0.0073 (15)	0.0050 (17)
C7	0.062 (2)	0.032 (2)	0.0393 (19)	0.0075 (18)	0.0096 (16)	0.0017 (17)
C8	0.0319 (16)	0.0319 (18)	0.0335 (16)	−0.0001 (16)	0.0053 (12)	0.0008 (16)
C9	0.0348 (17)	0.0331 (18)	0.0332 (17)	0.0046 (15)	0.0060 (13)	0.0003 (15)
C10	0.0305 (17)	0.037 (2)	0.0348 (18)	0.0010 (16)	0.0056 (13)	−0.0016 (16)
C11	0.062 (2)	0.047 (2)	0.039 (2)	0.023 (2)	0.0053 (16)	−0.0013 (18)
C12	0.048 (2)	0.040 (2)	0.0355 (18)	0.0160 (18)	−0.0006 (14)	0.0042 (17)
C13	0.0308 (16)	0.0337 (18)	0.0321 (17)	0.0025 (15)	0.0026 (13)	0.0015 (15)
C14	0.0300 (15)	0.0293 (17)	0.0297 (16)	0.0002 (15)	0.0009 (12)	−0.0036 (15)
C15	0.0404 (19)	0.0273 (19)	0.0383 (18)	−0.0007 (15)	0.0022 (14)	−0.0005 (14)
C16	0.048 (2)	0.033 (2)	0.0375 (19)	−0.0034 (16)	0.0017 (15)	−0.0098 (15)
C17	0.0344 (16)	0.043 (2)	0.0322 (16)	0.0006 (18)	−0.0037 (12)	−0.0027 (17)
C18	0.0339 (17)	0.0329 (18)	0.0302 (17)	0.0068 (15)	−0.0002 (13)	0.0026 (15)
C19	0.0416 (19)	0.038 (2)	0.0367 (18)	0.0017 (16)	0.0053 (14)	0.0020 (15)
C20	0.049 (2)	0.044 (2)	0.0406 (19)	0.0057 (18)	0.0070 (15)	0.0077 (17)
C21	0.064 (2)	0.059 (3)	0.0307 (18)	0.006 (2)	0.0063 (15)	−0.0005 (17)
C22	0.055 (2)	0.050 (2)	0.0375 (18)	0.006 (2)	−0.0072 (15)	−0.0046 (18)
C23	0.049 (2)	0.108 (4)	0.041 (2)	0.024 (2)	0.0024 (15)	0.008 (2)
C24	0.0469 (19)	0.062 (2)	0.0316 (18)	−0.004 (2)	0.0036 (14)	0.0036 (18)
C25	0.0339 (18)	0.057 (2)	0.0361 (18)	0.0045 (18)	0.0051 (13)	−0.0035 (18)
C26	0.046 (2)	0.064 (3)	0.046 (2)	−0.0171 (19)	0.0146 (16)	−0.0064 (19)
C27	0.0352 (16)	0.039 (2)	0.0240 (15)	0.0062 (18)	0.0000 (12)	0.0022 (16)
C28	0.0396 (19)	0.058 (3)	0.058 (2)	−0.007 (2)	−0.0073 (15)	−0.001 (2)
C29	0.067 (3)	0.046 (2)	0.059 (2)	−0.012 (2)	0.0168 (18)	−0.0017 (19)
C30	0.068 (3)	0.065 (3)	0.056 (2)	0.002 (2)	0.0234 (19)	0.008 (2)
O5	0.0564 (17)	0.085 (2)	0.110 (2)	−0.0215 (17)	0.0338 (16)	−0.033 (2)
C31	0.102 (4)	0.074 (4)	0.113 (4)	−0.001 (3)	0.058 (3)	−0.010 (3)

Geometric parameters (Å, º)

O1—C3	1.447 (4)	C15—H15B	0.9700
O1—H1	0.8200	C16—C17	1.531 (5)
O2—C24	1.430 (3)	C16—H16A	0.9700
O2—H2	0.8200	C16—H16B	0.9700
O3—C27	1.326 (4)	C17—C22	1.535 (4)
O3—H3	0.8200	C17—C28	1.537 (4)
O4—C27	1.213 (4)	C17—C18	1.552 (5)
C1—C2	1.532 (4)	C18—C19	1.558 (4)
C1—C10	1.538 (5)	C18—H18	0.9800
C1—H1A	0.9700	C19—C29	1.531 (5)
C1—H1B	0.9700	C19—C20	1.539 (4)
C2—C3	1.514 (5)	C19—H19	0.9800
C2—H2A	0.9700	C20—C21	1.516 (5)
C2—H2B	0.9700	C20—C30	1.529 (5)
C3—C4	1.539 (5)	C20—H20	0.9800
C3—H3A	0.9800	C21—C22	1.512 (5)
C4—C23	1.539 (5)	C21—H21A	0.9700
C4—C24	1.552 (5)	C21—H21B	0.9700
C4—C5	1.559 (4)	C22—H22A	0.9700
C5—C6	1.532 (5)	C22—H22B	0.9700
C5—C10	1.564 (4)	C23—H23A	0.9600
C5—H5	0.9800	C23—H23B	0.9600
C6—C7	1.515 (4)	C23—H23C	0.9600
C6—H6A	0.9700	C24—H24A	0.9700
C6—H6B	0.9700	C24—H24B	0.9700
C7—C8	1.550 (4)	C25—H25A	0.9600
C7—H7A	0.9700	C25—H25B	0.9600
C7—H7B	0.9700	C25—H25C	0.9600
C8—C26	1.539 (4)	C26—H26A	0.9600
C8—C9	1.559 (5)	C26—H26B	0.9600
C8—C14	1.607 (4)	C26—H26C	0.9600
C9—C11	1.529 (4)	C28—H28A	0.9600
C9—C10	1.577 (4)	C28—H28B	0.9600
C9—H9	0.9800	C28—H28C	0.9600
C10—C25	1.552 (4)	C29—H29A	0.9600
C11—C12	1.489 (4)	C29—H29B	0.9600
C11—H11A	0.9700	C29—H29C	0.9600
C11—H11B	0.9700	C30—H30A	0.9600
C12—C13	1.324 (5)	C30—H30B	0.9600
C12—H12	0.9300	C30—H30C	0.9600
C13—C18	1.537 (4)	O5—C31	1.400 (5)
C13—C14	1.538 (5)	O5—H5A	0.8200
C14—C27	1.541 (4)	C31—H31A	0.9600
C14—C15	1.550 (4)	C31—H31B	0.9600
C15—C16	1.518 (4)	C31—H31C	0.9600
C15—H15A	0.9700
C3—O1—H1	109.5	C17—C16—H16B	109.0
C24—O2—H2	109.5	H16A—C16—H16B	107.8
C27—O3—H3	109.5	C16—C17—C22	110.4 (3)
C2—C1—C10	113.1 (3)	C16—C17—C28	110.6 (3)
C2—C1—H1A	109.0	C22—C17—C28	108.0 (2)
C10—C1—H1A	109.0	C16—C17—C18	108.5 (2)
C2—C1—H1B	109.0	C22—C17—C18	110.5 (3)
C10—C1—H1B	109.0	C28—C17—C18	108.8 (3)
H1A—C1—H1B	107.8	C13—C18—C17	110.3 (3)
C3—C2—C1	112.5 (3)	C13—C18—C19	113.1 (2)
C3—C2—H2A	109.1	C17—C18—C19	114.4 (2)
C1—C2—H2A	109.1	C13—C18—H18	106.1
C3—C2—H2B	109.1	C17—C18—H18	106.1
C1—C2—H2B	109.1	C19—C18—H18	106.1
H2A—C2—H2B	107.8	C29—C19—C20	110.8 (3)
O1—C3—C2	108.4 (3)	C29—C19—C18	110.6 (3)
O1—C3—C4	108.8 (3)	C20—C19—C18	111.0 (2)
C2—C3—C4	115.4 (3)	C29—C19—H19	108.1
O1—C3—H3A	108.0	C20—C19—H19	108.1
C2—C3—H3A	108.0	C18—C19—H19	108.1
C4—C3—H3A	108.0	C21—C20—C30	110.6 (3)
C3—C4—C23	108.4 (3)	C21—C20—C19	111.5 (3)
C3—C4—C24	111.0 (3)	C30—C20—C19	112.3 (3)
C23—C4—C24	108.2 (3)	C21—C20—H20	107.4
C3—C4—C5	108.7 (3)	C30—C20—H20	107.4
C23—C4—C5	108.8 (3)	C19—C20—H20	107.4
C24—C4—C5	111.7 (3)	C22—C21—C20	112.0 (3)
C6—C5—C4	114.9 (3)	C22—C21—H21A	109.2
C6—C5—C10	110.4 (2)	C20—C21—H21A	109.2
C4—C5—C10	117.9 (3)	C22—C21—H21B	109.2
C6—C5—H5	103.9	C20—C21—H21B	109.2
C4—C5—H5	103.9	H21A—C21—H21B	107.9
C10—C5—H5	103.9	C21—C22—C17	114.1 (3)
C7—C6—C5	110.6 (3)	C21—C22—H22A	108.7
C7—C6—H6A	109.5	C17—C22—H22A	108.7
C5—C6—H6A	109.5	C21—C22—H22B	108.7
C7—C6—H6B	109.5	C17—C22—H22B	108.7
C5—C6—H6B	109.5	H22A—C22—H22B	107.6
H6A—C6—H6B	108.1	C4—C23—H23A	109.5
C6—C7—C8	113.5 (3)	C4—C23—H23B	109.5
C6—C7—H7A	108.9	H23A—C23—H23B	109.5
C8—C7—H7A	108.9	C4—C23—H23C	109.5
C6—C7—H7B	108.9	H23A—C23—H23C	109.5
C8—C7—H7B	108.9	H23B—C23—H23C	109.5
H7A—C7—H7B	107.7	O2—C24—C4	113.5 (3)
C26—C8—C7	108.6 (3)	O2—C24—H24A	108.9
C26—C8—C9	110.8 (3)	C4—C24—H24A	108.9
C7—C8—C9	109.2 (2)	O2—C24—H24B	108.9
C26—C8—C14	109.1 (2)	C4—C24—H24B	108.9
C7—C8—C14	109.3 (2)	H24A—C24—H24B	107.7
C9—C8—C14	109.9 (2)	C10—C25—H25A	109.5
C11—C9—C8	109.7 (2)	C10—C25—H25B	109.5
C11—C9—C10	113.4 (3)	H25A—C25—H25B	109.5
C8—C9—C10	117.0 (2)	C10—C25—H25C	109.5
C11—C9—H9	105.2	H25A—C25—H25C	109.5
C8—C9—H9	105.2	H25B—C25—H25C	109.5
C10—C9—H9	105.2	C8—C26—H26A	109.5
C1—C10—C25	107.9 (3)	C8—C26—H26B	109.5
C1—C10—C5	107.6 (2)	H26A—C26—H26B	109.5
C25—C10—C5	112.8 (3)	C8—C26—H26C	109.5
C1—C10—C9	107.8 (3)	H26A—C26—H26C	109.5
C25—C10—C9	113.6 (2)	H26B—C26—H26C	109.5
C5—C10—C9	106.9 (2)	O4—C27—O3	121.9 (3)
C12—C11—C9	112.9 (3)	O4—C27—C14	123.2 (3)
C12—C11—H11A	109.0	O3—C27—C14	114.8 (3)
C9—C11—H11A	109.0	C17—C28—H28A	109.5
C12—C11—H11B	109.0	C17—C28—H28B	109.5
C9—C11—H11B	109.0	H28A—C28—H28B	109.5
H11A—C11—H11B	107.8	C17—C28—H28C	109.5
C13—C12—C11	126.4 (3)	H28A—C28—H28C	109.5
C13—C12—H12	116.8	H28B—C28—H28C	109.5
C11—C12—H12	116.8	C19—C29—H29A	109.5
C12—C13—C18	119.9 (3)	C19—C29—H29B	109.5
C12—C13—C14	121.9 (3)	H29A—C29—H29B	109.5
C18—C13—C14	118.2 (3)	C19—C29—H29C	109.5
C13—C14—C27	109.4 (3)	H29A—C29—H29C	109.5
C13—C14—C15	110.0 (2)	H29B—C29—H29C	109.5
C27—C14—C15	106.5 (2)	C20—C30—H30A	109.5
C13—C14—C8	110.9 (2)	C20—C30—H30B	109.5
C27—C14—C8	108.9 (2)	H30A—C30—H30B	109.5
C15—C14—C8	110.9 (2)	C20—C30—H30C	109.5
C16—C15—C14	114.2 (3)	H30A—C30—H30C	109.5
C16—C15—H15A	108.7	H30B—C30—H30C	109.5
C14—C15—H15A	108.7	C31—O5—H5A	109.5
C16—C15—H15B	108.7	O5—C31—H31A	109.5
C14—C15—H15B	108.7	O5—C31—H31B	109.5
H15A—C15—H15B	107.6	H31A—C31—H31B	109.5
C15—C16—C17	112.9 (3)	O5—C31—H31C	109.5
C15—C16—H16A	109.0	H31A—C31—H31C	109.5
C17—C16—H16A	109.0	H31B—C31—H31C	109.5
C15—C16—H16B	109.0
C10—C1—C2—C3	55.9 (4)	C12—C13—C14—C8	12.0 (4)
C1—C2—C3—O1	−174.8 (3)	C18—C13—C14—C8	−166.5 (2)
C1—C2—C3—C4	−52.6 (4)	C26—C8—C14—C13	77.3 (3)
O1—C3—C4—C23	−72.9 (3)	C7—C8—C14—C13	−164.1 (3)
C2—C3—C4—C23	165.0 (3)	C9—C8—C14—C13	−44.3 (3)
O1—C3—C4—C24	45.8 (4)	C26—C8—C14—C27	−162.1 (3)
C2—C3—C4—C24	−76.3 (3)	C7—C8—C14—C27	−43.5 (3)
O1—C3—C4—C5	169.0 (2)	C9—C8—C14—C27	76.2 (3)
C2—C3—C4—C5	47.0 (4)	C26—C8—C14—C15	−45.2 (3)
C3—C4—C5—C6	178.8 (3)	C7—C8—C14—C15	73.4 (3)
C23—C4—C5—C6	61.0 (4)	C9—C8—C14—C15	−166.9 (2)
C24—C4—C5—C6	−58.4 (4)	C13—C14—C15—C16	44.3 (3)
C3—C4—C5—C10	−48.4 (4)	C27—C14—C15—C16	−74.2 (3)
C23—C4—C5—C10	−166.3 (3)	C8—C14—C15—C16	167.4 (3)
C24—C4—C5—C10	74.4 (4)	C14—C15—C16—C17	−55.6 (4)
C4—C5—C6—C7	−160.4 (2)	C15—C16—C17—C22	−178.8 (3)
C10—C5—C6—C7	63.4 (3)	C15—C16—C17—C28	−59.4 (4)
C5—C6—C7—C8	−59.1 (4)	C15—C16—C17—C18	59.9 (3)
C6—C7—C8—C26	−71.5 (3)	C12—C13—C18—C17	−128.1 (3)
C6—C7—C8—C9	49.4 (4)	C14—C13—C18—C17	50.4 (3)
C6—C7—C8—C14	169.6 (3)	C12—C13—C18—C19	102.3 (3)
C26—C8—C9—C11	−59.2 (3)	C14—C13—C18—C19	−79.1 (4)
C7—C8—C9—C11	−178.7 (2)	C16—C17—C18—C13	−55.4 (3)
C14—C8—C9—C11	61.4 (3)	C22—C17—C18—C13	−176.6 (2)
C26—C8—C9—C10	71.8 (3)	C28—C17—C18—C13	65.0 (3)
C7—C8—C9—C10	−47.7 (3)	C16—C17—C18—C19	73.5 (3)
C14—C8—C9—C10	−167.6 (2)	C22—C17—C18—C19	−47.8 (3)
C2—C1—C10—C25	68.5 (3)	C28—C17—C18—C19	−166.2 (3)
C2—C1—C10—C5	−53.5 (3)	C13—C18—C19—C29	−58.7 (3)
C2—C1—C10—C9	−168.4 (2)	C17—C18—C19—C29	173.9 (3)
C6—C5—C10—C1	−173.2 (3)	C13—C18—C19—C20	177.9 (3)
C4—C5—C10—C1	52.1 (3)	C17—C18—C19—C20	50.5 (3)
C6—C5—C10—C25	68.0 (3)	C29—C19—C20—C21	−177.1 (3)
C4—C5—C10—C25	−66.8 (4)	C18—C19—C20—C21	−53.8 (4)
C6—C5—C10—C9	−57.6 (3)	C29—C19—C20—C30	58.2 (4)
C4—C5—C10—C9	167.7 (3)	C18—C19—C20—C30	−178.5 (3)
C11—C9—C10—C1	−63.2 (3)	C30—C20—C21—C22	−177.7 (3)
C8—C9—C10—C1	167.5 (3)	C19—C20—C21—C22	56.6 (4)
C11—C9—C10—C25	56.3 (4)	C20—C21—C22—C17	−55.5 (4)
C8—C9—C10—C25	−73.0 (3)	C16—C17—C22—C21	−70.2 (4)
C11—C9—C10—C5	−178.6 (3)	C28—C17—C22—C21	168.8 (3)
C8—C9—C10—C5	52.1 (3)	C18—C17—C22—C21	49.9 (4)
C8—C9—C11—C12	−45.0 (4)	C3—C4—C24—O2	−70.3 (4)
C10—C9—C11—C12	−177.9 (3)	C23—C4—C24—O2	48.5 (4)
C9—C11—C12—C13	12.2 (5)	C5—C4—C24—O2	168.2 (3)
C11—C12—C13—C18	−176.6 (3)	C13—C14—C27—O4	−134.9 (3)
C11—C12—C13—C14	4.9 (5)	C15—C14—C27—O4	−16.1 (4)
C12—C13—C14—C27	−108.2 (3)	C8—C14—C27—O4	103.6 (3)
C18—C13—C14—C27	73.3 (3)	C13—C14—C27—O3	45.6 (3)
C12—C13—C14—C15	135.1 (3)	C15—C14—C27—O3	164.4 (2)
C18—C13—C14—C15	−43.4 (3)	C8—C14—C27—O3	−75.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4^i	0.82	1.91	2.728 (3)	173
O5—H5A···O2^i	0.82	1.85	2.667 (4)	178
O2—H2···O1	0.82	1.97	2.645 (5)	138
O3—H3···O5	0.82	1.80	2.618 (3)	173

Symmetry code: (i) −x+1, y+1/2, −z+1.