Cimigenol-3-O-β-D-xylopranoside methanol solvate

The title compound, (23R,24S)-16b,23:16a,24-diep­oxy-15a,25-dihydr­oxy-9,19-cyclo­lanostane-3-O-β-D-xylopyran­oside methanol solvate, C₃₅H₅₆O₉·CH₄O, is a cyclo­artane triterpene glycoside which was isolated from the rhizomes of Actaea asiatica. The mol­ecule contains five six-membered rings, two five-membered rings and a three-membered ring. The crystal structure is stabilized by intra- and inter­molecular O—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.007 Å
• Disorder in solvent or counterion
• R factor = 0.057
• wR factor = 0.183
• Data-to-parameter ratio = 10.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      50.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT413_ALERT_2_C Short Inter XH3 .. XHn     H2A    ..  H29A    ..       2.14 Ang.

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           28.32
           From the CIF: _reflns_number_total               4482
           Count of symmetry unique reflns         4664
           Completeness (_total/calc)             96.10%
           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 C5     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C17    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C20    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C23    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C24    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C31    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C32    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C33    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C34    = .          S

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

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

(23R, 24S)-16b,23:16a,24-diepoxy-15a,25-dihydroxy-9, 19-cyclolanostane-3-O-b-D-xylopyranoside

Crystal data

C35H56O9·CH4O	F(000) = 712
Mr = 652.84	Dx = 1.252 Mg m^−3
Monoclinic, P21	Melting point: 268 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 14.500 (3) Å	Cell parameters from 3138 reflections
b = 6.9301 (14) Å	θ = 2.7–26.4°
c = 17.267 (4) Å	µ = 0.09 mm^−1
β = 93.352 (4)°	T = 294 K
V = 1732.1 (6) Å^3	Block, colourless
Z = 2	0.22 × 0.18 × 0.10 mm

Data collection

Bruker SMART 1000 diffractometer	4482 independent reflections
Radiation source: fine-focus sealed tube	2630 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
φ and ω scans	θmax = 28.3°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −18→19
Tmin = 0.981, Tmax = 0.991	k = −9→8
10507 measured reflections	l = −12→22

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.183	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0865P)^2 + 0.4276P] where P = (Fo^2 + 2Fc^2)/3
4482 reflections	(Δ/σ)max = 0.001
449 parameters	Δρmax = 0.37 e Å^−3
27 restraints	Δρmin = −0.28 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	Occ. (<1)
O1	0.0685 (2)	0.6504 (5)	0.77002 (19)	0.0404 (8)
O2	0.2307 (3)	1.2168 (6)	0.2991 (2)	0.0530 (10)
H2	0.2125	1.1787	0.2559	0.080*
O3	0.4451 (2)	1.2107 (5)	0.2602 (2)	0.0435 (9)
O4	0.3335 (2)	1.0563 (5)	0.18862 (18)	0.0393 (8)
O5	0.2841 (3)	1.2263 (6)	0.0432 (2)	0.0558 (11)
H5	0.2644	1.3112	0.0136	0.084*
O6	−0.1036 (3)	0.7206 (6)	0.8355 (2)	0.0510 (9)
H6	−0.1040	0.8097	0.8667	0.076*
O7	−0.1433 (3)	0.4648 (7)	0.9613 (2)	0.0625 (12)
H7	−0.1943	0.5077	0.9473	0.094*
O8	−0.0860 (3)	0.0677 (6)	0.9306 (2)	0.0582 (11)
H8	−0.1194	0.0849	0.9667	0.087*
O9	0.0770 (2)	0.3564 (6)	0.8289 (2)	0.0494 (10)
C1	0.2000 (4)	0.5072 (8)	0.5946 (3)	0.0518 (14)
H1A	0.2568	0.4350	0.5903	0.062*
H1B	0.1510	0.4409	0.5645	0.062*
C2	0.1760 (5)	0.5181 (8)	0.6801 (3)	0.0568 (16)
H2A	0.1672	0.3887	0.6998	0.068*
H2B	0.2270	0.5767	0.7106	0.068*
C3	0.0888 (4)	0.6356 (7)	0.6891 (3)	0.0402 (12)
H3	0.0372	0.5691	0.6612	0.048*
C4	0.0950 (3)	0.8417 (7)	0.6561 (3)	0.0362 (11)
C5	0.1231 (3)	0.8227 (7)	0.5704 (3)	0.0360 (11)
H5A	0.0746	0.7436	0.5445	0.043*
C6	0.1207 (4)	1.0126 (8)	0.5261 (3)	0.0503 (14)
H6A	0.1626	1.1040	0.5522	0.060*
H6B	0.0589	1.0663	0.5250	0.060*
C7	0.1492 (3)	0.9800 (9)	0.4428 (3)	0.0498 (14)
H7A	0.1123	0.8772	0.4187	0.060*
H7B	0.1384	1.0966	0.4125	0.060*
C8	0.2510 (3)	0.9263 (7)	0.4443 (3)	0.0349 (11)
H8A	0.2841	1.0338	0.4702	0.042*
C9	0.2731 (3)	0.7465 (7)	0.4956 (3)	0.0339 (10)
C10	0.2114 (3)	0.7093 (7)	0.5631 (3)	0.0346 (11)
C11	0.3121 (3)	0.5708 (8)	0.4537 (3)	0.0409 (12)
H11A	0.2607	0.5017	0.4281	0.049*
H11B	0.3404	0.4852	0.4927	0.049*
C12	0.3836 (4)	0.6122 (8)	0.3930 (3)	0.0431 (12)
H12A	0.4439	0.5692	0.4134	0.052*
H12B	0.3675	0.5376	0.3466	0.052*
C13	0.3897 (3)	0.8272 (7)	0.3707 (3)	0.0342 (11)
C14	0.2901 (3)	0.9103 (7)	0.3637 (3)	0.0315 (10)
C15	0.3080 (3)	1.1068 (7)	0.3262 (3)	0.0373 (11)
H15	0.3409	1.1850	0.3662	0.045*
C16	0.3780 (3)	1.0627 (7)	0.2652 (3)	0.0338 (11)
C17	0.4242 (3)	0.8698 (8)	0.2888 (3)	0.0362 (11)
H17	0.3990	0.7700	0.2533	0.043*
C18	0.4522 (3)	0.9282 (9)	0.4338 (3)	0.0460 (13)
H18A	0.4251	0.9172	0.4830	0.069*
H18B	0.4585	1.0620	0.4208	0.069*
H18C	0.5120	0.8682	0.4368	0.069*
C19	0.3063 (3)	0.7942 (8)	0.5770 (3)	0.0390 (11)
H19A	0.3106	0.9294	0.5913	0.047*
H19B	0.3539	0.7127	0.6016	0.047*
C20	0.5298 (3)	0.8809 (9)	0.2797 (3)	0.0461 (13)
H20	0.5565	0.9625	0.3217	0.055*
C21	0.5783 (4)	0.6852 (10)	0.2857 (4)	0.0650 (18)
H21A	0.5457	0.5943	0.2523	0.097*
H21B	0.5792	0.6401	0.3383	0.097*
H21C	0.6406	0.6984	0.2702	0.097*
C22	0.5470 (4)	0.9815 (10)	0.2023 (3)	0.0564 (16)
H22A	0.6115	1.0190	0.2021	0.068*
H22B	0.5344	0.8915	0.1600	0.068*
C23	0.4865 (3)	1.1594 (9)	0.1895 (3)	0.0452 (13)
H23	0.5223	1.2674	0.1703	0.054*
C24	0.4000 (3)	1.1200 (8)	0.1351 (3)	0.0384 (11)
H24	0.4131	1.0142	0.0998	0.046*
C25	0.3637 (3)	1.2957 (8)	0.0876 (3)	0.0411 (12)
C26	0.4351 (4)	1.3507 (11)	0.0298 (4)	0.0684 (18)
H26A	0.4551	1.2368	0.0039	0.103*
H26B	0.4873	1.4106	0.0570	0.103*
H26C	0.4080	1.4392	−0.0077	0.103*
C27	0.3366 (4)	1.4641 (9)	0.1355 (4)	0.0622 (16)
H27A	0.3161	1.5679	0.1020	0.093*
H27B	0.3889	1.5057	0.1680	0.093*
H27C	0.2875	1.4268	0.1673	0.093*
C28	0.2263 (3)	0.7921 (8)	0.3082 (3)	0.0424 (13)
H28A	0.2151	0.6684	0.3309	0.064*
H28B	0.2551	0.7745	0.2600	0.064*
H28C	0.1688	0.8591	0.2989	0.064*
C29	0.1653 (4)	0.9595 (8)	0.7060 (3)	0.0482 (13)
H29A	0.1733	1.0835	0.6827	0.072*
H29B	0.2234	0.8926	0.7098	0.072*
H29C	0.1432	0.9760	0.7570	0.072*
C30	−0.0014 (4)	0.9357 (9)	0.6572 (3)	0.0542 (15)
H30A	−0.0252	0.9186	0.7075	0.081*
H30B	−0.0424	0.8758	0.6187	0.081*
H30C	0.0033	1.0709	0.6462	0.081*
C31	0.0157 (3)	0.5048 (7)	0.7985 (3)	0.0375 (11)
H31	−0.0253	0.4519	0.7567	0.045*
C32	−0.0412 (3)	0.5761 (7)	0.8640 (3)	0.0366 (11)
H32	−0.0001	0.6297	0.9056	0.044*
C33	−0.0960 (3)	0.4079 (8)	0.8955 (3)	0.0394 (12)
H33	−0.1417	0.3655	0.8550	0.047*
C34	−0.0343 (3)	0.2387 (8)	0.9182 (3)	0.0403 (12)
H34	0.0033	0.2705	0.9655	0.048*
C35	0.0280 (4)	0.1894 (8)	0.8546 (4)	0.0560 (15)
H35A	0.0722	0.0924	0.8731	0.067*
H35B	−0.0086	0.1352	0.8111	0.067*
O10	0.7960 (3)	0.0174 (9)	0.0551 (3)	0.0493 (17)	0.691 (7)
H10	0.8335	−0.0306	0.0896	0.074*	0.691 (7)
C36	0.7549 (9)	0.1927 (18)	0.0845 (8)	0.125 (5)	0.691 (7)
H36A	0.7459	0.1779	0.1389	0.187*	0.691 (7)
H36B	0.6964	0.2157	0.0571	0.187*	0.691 (7)
H36C	0.7953	0.3000	0.0770	0.187*	0.691 (7)
O10'	0.6922 (8)	0.335 (2)	0.0543 (8)	0.061 (4)	0.309 (7)
H10'	0.7417	0.3130	0.0354	0.092*	0.309 (7)
C36'	0.7061 (14)	0.464 (3)	0.1179 (10)	0.073 (5)	0.309 (7)
H36D	0.7699	0.5021	0.1227	0.110*	0.309 (7)
H36E	0.6900	0.4010	0.1647	0.110*	0.309 (7)
H36F	0.6680	0.5760	0.1091	0.110*	0.309 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0522 (19)	0.0346 (19)	0.0344 (18)	−0.0096 (16)	0.0020 (15)	−0.0026 (15)
O2	0.060 (2)	0.052 (2)	0.047 (2)	0.024 (2)	0.0054 (19)	0.013 (2)
O3	0.0486 (18)	0.039 (2)	0.043 (2)	−0.0094 (17)	0.0025 (16)	−0.0010 (17)
O4	0.0370 (16)	0.044 (2)	0.0363 (18)	−0.0099 (16)	0.0004 (14)	0.0083 (16)
O5	0.056 (2)	0.056 (3)	0.053 (2)	−0.014 (2)	−0.0114 (18)	0.016 (2)
O6	0.056 (2)	0.039 (2)	0.057 (2)	0.0103 (19)	−0.0012 (18)	0.0039 (19)
O7	0.072 (3)	0.065 (3)	0.054 (2)	0.020 (2)	0.031 (2)	0.010 (2)
O8	0.077 (3)	0.037 (2)	0.062 (3)	−0.002 (2)	0.021 (2)	0.003 (2)
O9	0.0485 (19)	0.045 (2)	0.056 (2)	0.0113 (18)	0.0118 (18)	0.0088 (19)
C1	0.073 (4)	0.029 (3)	0.055 (3)	0.002 (3)	0.020 (3)	0.002 (3)
C2	0.093 (4)	0.030 (3)	0.050 (3)	0.013 (3)	0.024 (3)	0.012 (3)
C3	0.054 (3)	0.032 (3)	0.035 (3)	−0.009 (2)	0.008 (2)	−0.006 (2)
C4	0.042 (2)	0.031 (3)	0.036 (3)	0.001 (2)	0.003 (2)	−0.003 (2)
C5	0.040 (2)	0.025 (2)	0.043 (3)	−0.002 (2)	0.000 (2)	−0.004 (2)
C6	0.053 (3)	0.039 (3)	0.060 (3)	0.018 (3)	0.016 (3)	0.012 (3)
C7	0.047 (3)	0.059 (4)	0.044 (3)	0.019 (3)	0.007 (2)	0.018 (3)
C8	0.032 (2)	0.033 (3)	0.039 (3)	0.003 (2)	−0.005 (2)	−0.003 (2)
C9	0.035 (2)	0.027 (2)	0.039 (3)	0.004 (2)	−0.004 (2)	0.000 (2)
C10	0.041 (2)	0.024 (2)	0.039 (3)	0.001 (2)	0.000 (2)	−0.001 (2)
C11	0.053 (3)	0.028 (2)	0.041 (3)	0.010 (2)	0.003 (2)	0.007 (2)
C12	0.050 (3)	0.033 (3)	0.047 (3)	0.010 (2)	0.002 (2)	−0.001 (2)
C13	0.031 (2)	0.033 (3)	0.037 (3)	0.003 (2)	−0.006 (2)	−0.002 (2)
C14	0.034 (2)	0.032 (2)	0.028 (2)	0.001 (2)	−0.0039 (19)	0.000 (2)
C15	0.045 (3)	0.030 (3)	0.037 (3)	0.004 (2)	−0.001 (2)	0.001 (2)
C16	0.037 (2)	0.035 (3)	0.028 (2)	−0.003 (2)	−0.0035 (19)	−0.001 (2)
C17	0.032 (2)	0.041 (3)	0.036 (3)	0.001 (2)	−0.002 (2)	−0.003 (2)
C18	0.039 (2)	0.056 (3)	0.042 (3)	−0.004 (3)	−0.007 (2)	−0.002 (3)
C19	0.042 (2)	0.035 (3)	0.039 (3)	0.007 (2)	−0.008 (2)	−0.001 (2)
C20	0.035 (2)	0.058 (4)	0.045 (3)	0.003 (3)	−0.001 (2)	0.000 (3)
C21	0.050 (3)	0.065 (5)	0.079 (5)	0.016 (3)	0.003 (3)	0.006 (4)
C22	0.040 (3)	0.068 (4)	0.062 (4)	0.005 (3)	0.010 (3)	0.007 (3)
C23	0.043 (3)	0.047 (3)	0.046 (3)	−0.009 (2)	0.007 (2)	0.003 (3)
C24	0.039 (2)	0.038 (3)	0.039 (3)	−0.008 (2)	0.007 (2)	0.004 (2)
C25	0.043 (3)	0.040 (3)	0.040 (3)	−0.007 (2)	0.003 (2)	0.002 (2)
C26	0.063 (4)	0.070 (4)	0.074 (4)	−0.004 (4)	0.019 (3)	0.026 (4)
C27	0.077 (4)	0.046 (3)	0.063 (4)	0.009 (3)	0.000 (3)	−0.001 (3)
C28	0.038 (2)	0.049 (3)	0.039 (3)	−0.006 (2)	−0.009 (2)	0.001 (2)
C29	0.061 (3)	0.033 (3)	0.051 (3)	−0.006 (3)	0.011 (3)	−0.008 (3)
C30	0.054 (3)	0.054 (4)	0.055 (3)	0.013 (3)	0.008 (3)	−0.002 (3)
C31	0.041 (2)	0.035 (3)	0.036 (3)	−0.005 (2)	−0.003 (2)	0.001 (2)
C32	0.038 (2)	0.035 (3)	0.036 (3)	0.006 (2)	−0.005 (2)	0.001 (2)
C33	0.043 (3)	0.042 (3)	0.033 (3)	0.005 (2)	0.003 (2)	0.000 (2)
C34	0.048 (3)	0.038 (3)	0.035 (3)	−0.002 (2)	0.002 (2)	0.001 (2)
C35	0.075 (4)	0.035 (3)	0.061 (4)	0.010 (3)	0.028 (3)	0.009 (3)
O10	0.040 (3)	0.067 (4)	0.040 (3)	−0.004 (3)	−0.007 (2)	−0.013 (3)
C36	0.104 (8)	0.174 (12)	0.095 (8)	−0.041 (9)	−0.003 (7)	0.015 (9)
O10'	0.040 (6)	0.084 (9)	0.059 (7)	−0.011 (7)	−0.005 (5)	0.036 (7)
C36'	0.062 (9)	0.103 (12)	0.054 (10)	−0.023 (10)	−0.006 (8)	0.026 (10)

Geometric parameters (Å, º)

O1—C31	1.375 (6)	C16—C17	1.540 (7)
O1—C3	1.449 (6)	C17—C20	1.550 (6)
O2—C15	1.413 (6)	C17—H17	0.9800
O2—H2	0.8200	C18—H18A	0.9600
O3—C16	1.420 (6)	C18—H18B	0.9600
O3—C23	1.435 (6)	C18—H18C	0.9600
O4—C16	1.438 (5)	C19—H19A	0.9700
O4—C24	1.443 (6)	C19—H19B	0.9700
O5—C25	1.431 (6)	C20—C21	1.528 (9)
O5—H5	0.8200	C20—C22	1.541 (8)
O6—C32	1.418 (6)	C20—H20	0.9800
O6—H6	0.8200	C21—H21A	0.9600
O7—C33	1.418 (6)	C21—H21B	0.9600
O7—H7	0.8200	C21—H21C	0.9600
O8—C34	1.425 (7)	C22—C23	1.522 (8)
O8—H8	0.8200	C22—H22A	0.9700
O9—C31	1.437 (6)	C22—H22B	0.9700
O9—C35	1.441 (7)	C23—C24	1.547 (7)
C1—C10	1.515 (7)	C23—H23	0.9800
C1—C2	1.540 (7)	C24—C25	1.543 (7)
C1—H1A	0.9700	C24—H24	0.9800
C1—H1B	0.9700	C25—C27	1.496 (8)
C2—C3	1.519 (8)	C25—C26	1.528 (8)
C2—H2A	0.9700	C26—H26A	0.9600
C2—H2B	0.9700	C26—H26B	0.9600
C3—C4	1.542 (7)	C26—H26C	0.9600
C3—H3	0.9800	C27—H27A	0.9600
C4—C29	1.531 (7)	C27—H27B	0.9600
C4—C30	1.544 (7)	C27—H27C	0.9600
C4—C5	1.563 (7)	C28—H28A	0.9600
C5—C10	1.514 (6)	C28—H28B	0.9600
C5—C6	1.521 (7)	C28—H28C	0.9600
C5—H5A	0.9800	C29—H29A	0.9600
C6—C7	1.537 (7)	C29—H29B	0.9600
C6—H6A	0.9700	C29—H29C	0.9600
C6—H6B	0.9700	C30—H30A	0.9600
C7—C8	1.521 (6)	C30—H30B	0.9600
C7—H7A	0.9700	C30—H30C	0.9600
C7—H7B	0.9700	C31—C32	1.521 (7)
C8—C14	1.538 (6)	C31—H31	0.9800
C8—C9	1.551 (7)	C32—C33	1.529 (7)
C8—H8A	0.9800	C32—H32	0.9800
C9—C19	1.496 (7)	C33—C34	1.513 (7)
C9—C10	1.531 (7)	C33—H33	0.9800
C9—C11	1.540 (7)	C34—C35	1.501 (7)
C10—C19	1.503 (6)	C34—H34	0.9800
C11—C12	1.544 (7)	C35—H35A	0.9700
C11—H11A	0.9700	C35—H35B	0.9700
C11—H11B	0.9700	O10—C36	1.458 (9)
C12—C13	1.542 (7)	O10—H10	0.8503
C12—H12A	0.9700	C36—H36A	0.9600
C12—H12B	0.9700	C36—H36B	0.9600
C13—C18	1.543 (7)	C36—H36C	0.9600
C13—C14	1.553 (6)	O10'—C36'	1.423 (10)
C13—C17	1.557 (7)	O10'—H10'	0.8200
C14—C28	1.530 (6)	C36'—H36D	0.9600
C14—C15	1.537 (7)	C36'—H36E	0.9600
C15—C16	1.535 (7)	C36'—H36F	0.9600
C15—H15	0.9800
C31—O1—C3	116.3 (4)	C13—C18—H18C	109.5
C15—O2—H2	109.5	H18A—C18—H18C	109.5
C16—O3—C23	101.2 (4)	H18B—C18—H18C	109.5
C16—O4—C24	107.3 (3)	C9—C19—C10	61.4 (3)
C25—O5—H5	109.5	C9—C19—H19A	117.6
C32—O6—H6	109.5	C10—C19—H19A	117.6
C33—O7—H7	109.5	C9—C19—H19B	117.6
C34—O8—H8	109.5	C10—C19—H19B	117.6
C31—O9—C35	112.4 (4)	H19A—C19—H19B	114.7
C10—C1—C2	109.6 (4)	C21—C20—C22	111.3 (5)
C10—C1—H1A	109.8	C21—C20—C17	113.7 (5)
C2—C1—H1A	109.8	C22—C20—C17	108.7 (4)
C10—C1—H1B	109.8	C21—C20—H20	107.6
C2—C1—H1B	109.8	C22—C20—H20	107.6
H1A—C1—H1B	108.2	C17—C20—H20	107.6
C3—C2—C1	111.0 (5)	C20—C21—H21A	109.5
C3—C2—H2A	109.4	C20—C21—H21B	109.5
C1—C2—H2A	109.4	H21A—C21—H21B	109.5
C3—C2—H2B	109.4	C20—C21—H21C	109.5
C1—C2—H2B	109.4	H21A—C21—H21C	109.5
H2A—C2—H2B	108.0	H21B—C21—H21C	109.5
O1—C3—C2	110.7 (4)	C23—C22—C20	111.8 (5)
O1—C3—C4	108.1 (4)	C23—C22—H22A	109.3
C2—C3—C4	113.1 (4)	C20—C22—H22A	109.3
O1—C3—H3	108.3	C23—C22—H22B	109.3
C2—C3—H3	108.3	C20—C22—H22B	109.3
C4—C3—H3	108.3	H22A—C22—H22B	107.9
C29—C4—C3	109.7 (4)	O3—C23—C22	110.1 (4)
C29—C4—C30	110.0 (4)	O3—C23—C24	101.2 (4)
C3—C4—C30	108.3 (4)	C22—C23—C24	112.6 (5)
C29—C4—C5	112.1 (4)	O3—C23—H23	110.8
C3—C4—C5	107.2 (4)	C22—C23—H23	110.8
C30—C4—C5	109.5 (4)	C24—C23—H23	110.8
C10—C5—C6	113.7 (4)	O4—C24—C25	111.2 (4)
C10—C5—C4	113.0 (4)	O4—C24—C23	102.4 (4)
C6—C5—C4	113.8 (4)	C25—C24—C23	115.0 (4)
C10—C5—H5A	105.1	O4—C24—H24	109.3
C6—C5—H5A	105.1	C25—C24—H24	109.3
C4—C5—H5A	105.1	C23—C24—H24	109.3
C5—C6—C7	110.1 (5)	O5—C25—C27	109.2 (5)
C5—C6—H6A	109.6	O5—C25—C26	106.9 (5)
C7—C6—H6A	109.6	C27—C25—C26	112.1 (5)
C5—C6—H6B	109.6	O5—C25—C24	105.0 (4)
C7—C6—H6B	109.6	C27—C25—C24	114.5 (4)
H6A—C6—H6B	108.2	C26—C25—C24	108.7 (4)
C8—C7—C6	109.4 (4)	C25—C26—H26A	109.5
C8—C7—H7A	109.8	C25—C26—H26B	109.5
C6—C7—H7A	109.8	H26A—C26—H26B	109.5
C8—C7—H7B	109.8	C25—C26—H26C	109.5
C6—C7—H7B	109.8	H26A—C26—H26C	109.5
H7A—C7—H7B	108.2	H26B—C26—H26C	109.5
C7—C8—C14	114.2 (4)	C25—C27—H27A	109.5
C7—C8—C9	112.0 (4)	C25—C27—H27B	109.5
C14—C8—C9	112.6 (4)	H27A—C27—H27B	109.5
C7—C8—H8A	105.7	C25—C27—H27C	109.5
C14—C8—H8A	105.7	H27A—C27—H27C	109.5
C9—C8—H8A	105.7	H27B—C27—H27C	109.5
C19—C9—C10	59.5 (3)	C14—C28—H28A	109.5
C19—C9—C11	120.6 (4)	C14—C28—H28B	109.5
C10—C9—C11	118.1 (4)	H28A—C28—H28B	109.5
C19—C9—C8	113.8 (4)	C14—C28—H28C	109.5
C10—C9—C8	117.3 (4)	H28A—C28—H28C	109.5
C11—C9—C8	115.9 (4)	H28B—C28—H28C	109.5
C19—C10—C5	123.6 (4)	C4—C29—H29A	109.5
C19—C10—C1	115.0 (4)	C4—C29—H29B	109.5
C5—C10—C1	109.8 (4)	H29A—C29—H29B	109.5
C19—C10—C9	59.1 (3)	C4—C29—H29C	109.5
C5—C10—C9	120.7 (4)	H29A—C29—H29C	109.5
C1—C10—C9	120.7 (4)	H29B—C29—H29C	109.5
C9—C11—C12	116.8 (4)	C4—C30—H30A	109.5
C9—C11—H11A	108.1	C4—C30—H30B	109.5
C12—C11—H11A	108.1	H30A—C30—H30B	109.5
C9—C11—H11B	108.1	C4—C30—H30C	109.5
C12—C11—H11B	108.1	H30A—C30—H30C	109.5
H11A—C11—H11B	107.3	H30B—C30—H30C	109.5
C13—C12—C11	113.6 (4)	O1—C31—O9	108.1 (4)
C13—C12—H12A	108.9	O1—C31—C32	111.4 (4)
C11—C12—H12A	108.9	O9—C31—C32	108.2 (4)
C13—C12—H12B	108.9	O1—C31—H31	109.7
C11—C12—H12B	108.9	O9—C31—H31	109.7
H12A—C12—H12B	107.7	C32—C31—H31	109.7
C12—C13—C18	107.6 (4)	O6—C32—C31	109.6 (4)
C12—C13—C14	108.1 (4)	O6—C32—C33	109.2 (4)
C18—C13—C14	113.1 (4)	C31—C32—C33	109.5 (4)
C12—C13—C17	115.9 (4)	O6—C32—H32	109.6
C18—C13—C17	110.4 (4)	C31—C32—H32	109.6
C14—C13—C17	101.9 (3)	C33—C32—H32	109.6
C28—C14—C15	108.7 (4)	O7—C33—C34	108.4 (4)
C28—C14—C8	111.4 (4)	O7—C33—C32	111.0 (4)
C15—C14—C8	113.5 (4)	C34—C33—C32	111.8 (4)
C28—C14—C13	112.1 (4)	O7—C33—H33	108.5
C15—C14—C13	100.5 (4)	C34—C33—H33	108.5
C8—C14—C13	110.2 (3)	C32—C33—H33	108.5
O2—C15—C16	115.1 (4)	O8—C34—C35	105.4 (4)
O2—C15—C14	117.8 (4)	O8—C34—C33	112.0 (4)
C16—C15—C14	104.3 (4)	C35—C34—C33	111.0 (4)
O2—C15—H15	106.2	O8—C34—H34	109.4
C16—C15—H15	106.2	C35—C34—H34	109.4
C14—C15—H15	106.2	C33—C34—H34	109.4
O3—C16—O4	103.8 (3)	O9—C35—C34	111.8 (5)
O3—C16—C15	112.4 (4)	O9—C35—H35A	109.3
O4—C16—C15	110.9 (4)	C34—C35—H35A	109.3
O3—C16—C17	110.8 (3)	O9—C35—H35B	109.3
O4—C16—C17	112.4 (4)	C34—C35—H35B	109.3
C15—C16—C17	106.6 (4)	H35A—C35—H35B	107.9
C16—C17—C20	110.3 (4)	C36—O10—H10	109.9
C16—C17—C13	104.3 (4)	C36'—O10'—H10'	109.5
C20—C17—C13	118.3 (4)	O10'—C36'—H36D	109.5
C16—C17—H17	107.8	O10'—C36'—H36E	109.5
C20—C17—H17	107.8	H36D—C36'—H36E	109.5
C13—C17—H17	107.8	O10'—C36'—H36F	109.5
C13—C18—H18A	109.5	H36D—C36'—H36F	109.5
C13—C18—H18B	109.5	H36E—C36'—H36F	109.5
H18A—C18—H18B	109.5
C10—C1—C2—C3	57.7 (7)	C8—C14—C15—C16	159.1 (3)
C31—O1—C3—C2	−88.0 (5)	C13—C14—C15—C16	41.4 (4)
C31—O1—C3—C4	147.7 (4)	C23—O3—C16—O4	−47.1 (4)
C1—C2—C3—O1	−178.1 (4)	C23—O3—C16—C15	−167.1 (4)
C1—C2—C3—C4	−56.7 (6)	C23—O3—C16—C17	73.8 (4)
O1—C3—C4—C29	54.5 (5)	C24—O4—C16—O3	28.2 (5)
C2—C3—C4—C29	−68.3 (5)	C24—O4—C16—C15	149.1 (4)
O1—C3—C4—C30	−65.5 (5)	C24—O4—C16—C17	−91.6 (4)
C2—C3—C4—C30	171.6 (4)	O2—C15—C16—O3	87.4 (5)
O1—C3—C4—C5	176.5 (4)	C14—C15—C16—O3	−141.9 (4)
C2—C3—C4—C5	53.6 (5)	O2—C15—C16—O4	−28.3 (6)
C29—C4—C5—C10	64.9 (5)	C14—C15—C16—O4	102.4 (4)
C3—C4—C5—C10	−55.5 (5)	O2—C15—C16—C17	−151.1 (4)
C30—C4—C5—C10	−172.7 (4)	C14—C15—C16—C17	−20.4 (5)
C29—C4—C5—C6	−66.7 (6)	O3—C16—C17—C20	−14.4 (5)
C3—C4—C5—C6	172.9 (4)	O4—C16—C17—C20	101.3 (4)
C30—C4—C5—C6	55.6 (6)	C15—C16—C17—C20	−136.9 (4)
C10—C5—C6—C7	48.7 (6)	O3—C16—C17—C13	113.6 (4)
C4—C5—C6—C7	−180.0 (4)	O4—C16—C17—C13	−130.7 (4)
C5—C6—C7—C8	−68.2 (6)	C15—C16—C17—C13	−8.9 (5)
C6—C7—C8—C14	−174.0 (4)	C12—C13—C17—C16	151.5 (4)
C6—C7—C8—C9	56.5 (6)	C18—C13—C17—C16	−85.9 (4)
C7—C8—C9—C19	−94.8 (5)	C14—C13—C17—C16	34.5 (4)
C14—C8—C9—C19	134.9 (4)	C12—C13—C17—C20	−85.5 (6)
C7—C8—C9—C10	−28.1 (6)	C18—C13—C17—C20	37.0 (6)
C14—C8—C9—C10	−158.5 (4)	C14—C13—C17—C20	157.4 (5)
C7—C8—C9—C11	119.0 (5)	C11—C9—C19—C10	−106.6 (5)
C14—C8—C9—C11	−11.4 (6)	C8—C9—C19—C10	108.8 (4)
C6—C5—C10—C19	50.3 (6)	C5—C10—C19—C9	−108.4 (5)
C4—C5—C10—C19	−81.4 (6)	C1—C10—C19—C9	112.1 (5)
C6—C5—C10—C1	−168.4 (5)	C16—C17—C20—C21	−168.1 (5)
C4—C5—C10—C1	59.9 (5)	C13—C17—C20—C21	72.0 (6)
C6—C5—C10—C9	−20.9 (6)	C16—C17—C20—C22	−43.5 (6)
C4—C5—C10—C9	−152.6 (4)	C13—C17—C20—C22	−163.4 (5)
C2—C1—C10—C19	86.0 (6)	C21—C20—C22—C23	170.4 (5)
C2—C1—C10—C5	−58.9 (6)	C17—C20—C22—C23	44.4 (7)
C2—C1—C10—C9	153.6 (4)	C16—O3—C23—C22	−72.9 (4)
C11—C9—C10—C19	110.8 (5)	C16—O3—C23—C24	46.4 (4)
C8—C9—C10—C19	−102.8 (5)	C20—C22—C23—O3	13.0 (6)
C19—C9—C10—C5	113.3 (5)	C20—C22—C23—C24	−99.2 (6)
C11—C9—C10—C5	−135.9 (4)	C16—O4—C24—C25	−122.5 (4)
C8—C9—C10—C5	10.5 (6)	C16—O4—C24—C23	0.9 (5)
C19—C9—C10—C1	−102.6 (5)	O3—C23—C24—O4	−29.0 (5)
C11—C9—C10—C1	8.1 (7)	C22—C23—C24—O4	88.6 (5)
C8—C9—C10—C1	154.5 (5)	O3—C23—C24—C25	91.8 (5)
C19—C9—C11—C12	−103.2 (5)	C22—C23—C24—C25	−150.7 (5)
C10—C9—C11—C12	−172.5 (4)	O4—C24—C25—O5	−63.5 (5)
C8—C9—C11—C12	40.6 (6)	C23—C24—C25—O5	−179.2 (4)
C9—C11—C12—C13	−12.5 (6)	O4—C24—C25—C27	56.3 (6)
C11—C12—C13—C18	81.8 (5)	C23—C24—C25—C27	−59.5 (6)
C11—C12—C13—C14	−40.7 (6)	O4—C24—C25—C26	−177.6 (5)
C11—C12—C13—C17	−154.2 (4)	C23—C24—C25—C26	66.7 (6)
C7—C8—C14—C28	−46.9 (6)	C3—O1—C31—O9	90.5 (5)
C9—C8—C14—C28	82.3 (5)	C3—O1—C31—C32	−150.7 (4)
C7—C8—C14—C15	76.2 (5)	C35—O9—C31—O1	−175.3 (4)
C9—C8—C14—C15	−154.6 (4)	C35—O9—C31—C32	63.9 (5)
C7—C8—C14—C13	−172.0 (4)	O1—C31—C32—O6	62.3 (5)
C9—C8—C14—C13	−42.8 (5)	O9—C31—C32—O6	−179.0 (4)
C12—C13—C14—C28	−53.9 (5)	O1—C31—C32—C33	−178.1 (4)
C18—C13—C14—C28	−172.9 (4)	O9—C31—C32—C33	−59.4 (5)
C17—C13—C14—C28	68.7 (5)	O6—C32—C33—O7	−65.5 (5)
C12—C13—C14—C15	−169.2 (4)	C31—C32—C33—O7	174.6 (4)
C18—C13—C14—C15	71.7 (5)	O6—C32—C33—C34	173.3 (4)
C17—C13—C14—C15	−46.7 (4)	C31—C32—C33—C34	53.4 (5)
C12—C13—C14—C8	70.8 (5)	O7—C33—C34—O8	70.7 (5)
C18—C13—C14—C8	−48.3 (5)	C32—C33—C34—O8	−166.6 (4)
C17—C13—C14—C8	−166.7 (4)	O7—C33—C34—C35	−171.8 (5)
C28—C14—C15—O2	52.7 (5)	C32—C33—C34—C35	−49.1 (6)
C8—C14—C15—O2	−71.8 (5)	C31—O9—C35—C34	−60.5 (6)
C13—C14—C15—O2	170.5 (4)	O8—C34—C35—O9	172.9 (5)
C28—C14—C15—C16	−76.4 (5)	C33—C34—C35—O9	51.4 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O6^i	0.82	2.19	2.880 (5)	143
O2—H2···O4	0.82	2.32	2.726 (5)	111
O5—H5···O10^ii	0.82	2.02	2.841 (7)	175
O6—H6···O8^iii	0.82	2.11	2.916 (6)	168
O7—H7···O5^iv	0.82	2.01	2.727 (6)	146
O8—H8···O10^v	0.82	2.07	2.846 (6)	159
O10—H10···O9^vi	0.85	2.02	2.867 (6)	180
O10′—H10′···O7^vii	0.82	2.40	3.087 (13)	142

Symmetry codes: (i) −x, y+1/2, −z+1; (ii) −x+1, y+3/2, −z; (iii) x, y+1, z; (iv) −x, y−1/2, −z+1; (v) x−1, y, z+1; (vi) −x+1, y−1/2, −z+1; (vii) x+1, y, z−1.