Cimicidol-3-one: a cyclo­artenol triterpenoid from the rhizomes of Cimicifuga racemosa

The title compound [systematic name: (20R,24R)-11β,24,25-tri­hydr­oxy-9,19-cyclo­lanost-7-ene-3,16,23-trione], C₃₀H₄₄O₆, is a cyclo­artenol triterpenoid which was isolated from the rhizomes of Cimicifuga racemosa. The mol­ecule contains three six-membered rings adopting chair and distorted boat conformations, a five-membered ring exhibiting an envelope conformation and a three-membered ring. The mol­ecules are linked by three hydrogen bonds, forming a two-dimensional structure parallel to the (001) plane.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.050
• wR factor = 0.137
• Data-to-parameter ratio = 10.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.03 Ratio
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C25

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.47 Ratio

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               3368
           Count of symmetry unique reflns         3368
           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
   2 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

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

---

Computing details

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Siemens, 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.

(20R,24R)-11β,24,25-trihydroxy-9,19-cyclolanost-7-ene-3,16,23-trione

Crystal data

C30H44O6	Dx = 1.207 Mg m^−3
Mr = 500.65	Melting point: 472 K
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 8.809 (1) Å	Cell parameters from 29 reflections
b = 9.236 (2) Å	θ = 3.4–14.7°
c = 16.944 (3) Å	µ = 0.08 mm^−1
β = 91.88 (1)°	T = 296 K
V = 1377.9 (4) Å^3	Prism, colourless
Z = 2	0.52 × 0.50 × 0.44 mm
F(000) = 544

Data collection

Siemens P4 diffractometer	Rint = 0.017
Radiation source: normal-focus sealed tube	θmax = 27.5°, θmin = 1.2°
Graphite monochromator	h = 0→11
ω scans	k = 0→12
3702 measured reflections	l = −22→22
3368 independent reflections	3 standard reflections every 97 reflections
2585 reflections with I > 2σ(I)	intensity decay: 5.7%

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.050	w = 1/[σ^2(Fo^2) + (0.0926P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.137	(Δ/σ)max < 0.001
S = 0.98	Δρmax = 0.35 e Å^−3
3368 reflections	Δρmin = −0.21 e Å^−3
336 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.010 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: calculation of Flack Parameter suppressed
Secondary atom site location: difference Fourier map

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	0.9551 (4)	0.5337 (4)	−0.09063 (17)	0.0995 (12)
O2	0.8976 (2)	0.7557 (3)	0.26874 (13)	0.0574 (6)
H2O	0.9521	0.7295	0.3062	0.069*
O3	0.1298 (2)	0.6793 (3)	0.38039 (13)	0.0586 (6)
O4	0.1675 (3)	0.9126 (3)	0.53909 (19)	0.0794 (9)
O5	−0.0911 (4)	0.8338 (4)	0.5880 (3)	0.1272 (17)
H5O	−0.0527	0.9113	0.5759	0.153*
O6	0.1325 (4)	0.5235 (4)	0.6429 (2)	0.1028 (12)
H6O	0.1236	0.4615	0.6771	0.123*
C1	0.9202 (3)	0.6286 (4)	0.10430 (18)	0.0525 (8)
H1A	0.9187	0.5243	0.1107	0.063*
H1B	0.9781	0.6697	0.1485	0.063*
C2	0.9964 (3)	0.6668 (5)	0.02745 (18)	0.0603 (9)
H2A	1.0078	0.7710	0.0236	0.072*
H2B	1.0968	0.6237	0.0272	0.072*
C3	0.9033 (4)	0.6125 (4)	−0.04189 (19)	0.0547 (8)
C4	0.7391 (3)	0.6653 (4)	−0.04722 (16)	0.0441 (7)
C5	0.6628 (3)	0.6328 (3)	0.03295 (14)	0.0379 (6)
H5	0.6578	0.5272	0.0376	0.046*
C6	0.5002 (3)	0.6870 (4)	0.03321 (14)	0.0456 (7)
H6A	0.4978	0.7890	0.0197	0.055*
H6B	0.4397	0.6351	−0.0065	0.055*
C7	0.4326 (3)	0.6658 (4)	0.11268 (15)	0.0400 (6)
H7	0.3281	0.6525	0.1146	0.048*
C8	0.5128 (3)	0.6649 (3)	0.18037 (14)	0.0323 (5)
C9	0.6799 (3)	0.6996 (3)	0.18349 (14)	0.0338 (6)
C10	0.7591 (3)	0.6864 (3)	0.10404 (14)	0.0370 (6)
C11	0.7690 (3)	0.6612 (4)	0.26092 (15)	0.0392 (6)
H11	0.8073	0.5622	0.2556	0.047*
C12	0.6798 (3)	0.6678 (4)	0.33684 (15)	0.0432 (7)
H12A	0.6861	0.5739	0.3623	0.052*
H12B	0.7289	0.7374	0.3722	0.052*
C13	0.5126 (3)	0.7090 (3)	0.32656 (15)	0.0334 (6)
C14	0.4436 (3)	0.6183 (3)	0.25652 (15)	0.0343 (6)
C15	0.2719 (3)	0.6448 (4)	0.26300 (16)	0.0465 (8)
H15A	0.2405	0.7312	0.2343	0.056*
H15B	0.2138	0.5629	0.2428	0.056*
C16	0.2521 (3)	0.6635 (4)	0.35125 (16)	0.0421 (6)
C17	0.4054 (3)	0.6669 (3)	0.39456 (14)	0.0372 (6)
H17	0.4296	0.5663	0.4084	0.045*
C18	0.4987 (3)	0.8715 (3)	0.30985 (17)	0.0430 (7)
H18A	0.5315	0.9249	0.3559	0.052*
H18B	0.3947	0.8948	0.2966	0.052*
H18C	0.5611	0.8965	0.2665	0.052*
C19	0.7292 (3)	0.8326 (3)	0.13850 (16)	0.0384 (6)
H19A	0.6505	0.8913	0.1131	0.046*
H19B	0.8156	0.8866	0.1598	0.046*
C20	0.4093 (4)	0.7516 (4)	0.47247 (17)	0.0474 (7)
H20	0.3791	0.8517	0.4609	0.057*
C21	0.5675 (4)	0.7540 (5)	0.5113 (2)	0.0675 (11)
H21A	0.5629	0.7964	0.5628	0.081*
H21B	0.6340	0.8102	0.4796	0.081*
H21C	0.6055	0.6568	0.5158	0.081*
C22	0.2948 (4)	0.6872 (4)	0.52985 (17)	0.0511 (8)
H22A	0.2562	0.5970	0.5078	0.061*
H22B	0.3485	0.6644	0.5792	0.061*
C23	0.1623 (4)	0.7830 (4)	0.54736 (19)	0.0529 (8)
C24	0.0175 (4)	0.7184 (5)	0.5778 (2)	0.0659 (10)
H24	−0.0241	0.6510	0.5381	0.079*
C25	0.0297 (4)	0.6401 (5)	0.6568 (2)	0.0635 (10)
C26	−0.1205 (5)	0.5760 (5)	0.6780 (3)	0.0843 (13)
H26A	−0.1534	0.5087	0.6378	0.101*
H26B	−0.1944	0.6519	0.6820	0.101*
H26C	−0.1096	0.5266	0.7277	0.101*
C27	0.0956 (7)	0.7299 (9)	0.7210 (3)	0.130 (3)
H27A	0.0735	0.6871	0.7710	0.156*
H27B	0.0528	0.8254	0.7181	0.156*
H27C	0.2037	0.7357	0.7159	0.156*
C28	0.4733 (4)	0.4543 (3)	0.26524 (18)	0.0513 (8)
H28A	0.4238	0.4037	0.2221	0.062*
H28B	0.4341	0.4209	0.3142	0.062*
H28C	0.5806	0.4363	0.2648	0.062*
C29	0.6546 (5)	0.5867 (5)	−0.11555 (19)	0.0662 (10)
H29A	0.7056	0.6042	−0.1638	0.079*
H29B	0.5523	0.6222	−0.1204	0.079*
H29C	0.6531	0.4846	−0.1050	0.079*
C30	0.7455 (4)	0.8278 (4)	−0.0647 (2)	0.0547 (8)
H30A	0.7859	0.8780	−0.0191	0.066*
H30B	0.6450	0.8627	−0.0774	0.066*
H30C	0.8095	0.8445	−0.1085	0.066*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.108 (2)	0.118 (3)	0.0746 (17)	0.049 (2)	0.0281 (16)	−0.025 (2)
O2	0.0318 (10)	0.0875 (18)	0.0523 (13)	−0.0053 (11)	−0.0052 (9)	−0.0038 (12)
O3	0.0384 (11)	0.0852 (18)	0.0530 (12)	−0.0049 (13)	0.0130 (9)	0.0016 (13)
O4	0.0665 (17)	0.0537 (17)	0.119 (2)	−0.0018 (14)	0.0225 (16)	0.0021 (16)
O5	0.0594 (18)	0.085 (2)	0.239 (5)	0.0152 (19)	0.039 (2)	0.049 (3)
O6	0.088 (2)	0.091 (2)	0.133 (3)	0.0225 (19)	0.055 (2)	0.056 (2)
C1	0.0422 (15)	0.065 (2)	0.0505 (16)	0.0181 (15)	0.0097 (13)	−0.0025 (16)
C2	0.0417 (15)	0.076 (2)	0.064 (2)	0.0140 (18)	0.0169 (14)	0.002 (2)
C3	0.0622 (19)	0.0538 (19)	0.0496 (17)	0.0136 (17)	0.0231 (15)	0.0067 (16)
C4	0.0532 (16)	0.0423 (16)	0.0374 (13)	0.0010 (15)	0.0105 (12)	0.0028 (13)
C5	0.0450 (14)	0.0354 (15)	0.0338 (12)	0.0006 (12)	0.0064 (11)	0.0023 (11)
C6	0.0422 (14)	0.060 (2)	0.0340 (13)	−0.0004 (15)	−0.0005 (11)	0.0031 (14)
C7	0.0308 (12)	0.0496 (16)	0.0395 (13)	−0.0023 (13)	0.0010 (10)	−0.0001 (13)
C8	0.0296 (11)	0.0342 (13)	0.0333 (12)	0.0019 (11)	0.0027 (9)	−0.0020 (11)
C9	0.0300 (12)	0.0370 (15)	0.0343 (12)	0.0042 (11)	0.0010 (9)	−0.0007 (11)
C10	0.0338 (12)	0.0421 (16)	0.0355 (13)	0.0047 (12)	0.0072 (10)	0.0033 (12)
C11	0.0322 (12)	0.0439 (16)	0.0414 (14)	0.0076 (13)	−0.0017 (10)	−0.0026 (13)
C12	0.0376 (13)	0.0581 (18)	0.0335 (12)	0.0050 (15)	−0.0030 (10)	0.0003 (14)
C13	0.0311 (12)	0.0369 (14)	0.0322 (11)	−0.0005 (11)	0.0024 (9)	−0.0006 (11)
C14	0.0340 (12)	0.0382 (14)	0.0308 (12)	−0.0020 (11)	0.0015 (10)	0.0001 (11)
C15	0.0353 (13)	0.065 (2)	0.0389 (14)	−0.0104 (15)	0.0022 (10)	−0.0005 (14)
C16	0.0414 (14)	0.0450 (16)	0.0402 (14)	−0.0059 (14)	0.0061 (11)	0.0014 (13)
C17	0.0413 (13)	0.0368 (14)	0.0339 (12)	−0.0012 (13)	0.0049 (10)	0.0022 (12)
C18	0.0447 (15)	0.0392 (16)	0.0457 (15)	−0.0006 (13)	0.0093 (12)	−0.0022 (13)
C19	0.0351 (13)	0.0391 (15)	0.0411 (14)	−0.0005 (12)	0.0051 (11)	0.0012 (12)
C20	0.0628 (19)	0.0430 (17)	0.0372 (14)	−0.0008 (15)	0.0134 (13)	−0.0027 (13)
C21	0.074 (2)	0.090 (3)	0.0387 (16)	−0.025 (2)	0.0031 (16)	−0.0195 (18)
C22	0.0650 (19)	0.0502 (19)	0.0388 (14)	0.0015 (17)	0.0143 (13)	0.0033 (14)
C23	0.0488 (18)	0.058 (2)	0.0519 (18)	−0.0100 (16)	0.0009 (14)	0.0000 (16)
C24	0.0453 (18)	0.063 (2)	0.089 (3)	−0.0061 (17)	−0.0010 (17)	0.007 (2)
C25	0.0560 (19)	0.069 (3)	0.066 (2)	−0.0152 (19)	0.0200 (16)	−0.0072 (19)
C26	0.064 (2)	0.080 (3)	0.111 (3)	−0.018 (2)	0.033 (2)	0.003 (3)
C27	0.149 (6)	0.152 (7)	0.089 (4)	−0.076 (5)	0.010 (4)	−0.008 (4)
C28	0.071 (2)	0.0405 (17)	0.0431 (16)	−0.0062 (16)	0.0065 (15)	−0.0029 (14)
C29	0.083 (2)	0.074 (3)	0.0429 (17)	−0.017 (2)	0.0167 (16)	−0.0113 (17)
C30	0.0625 (19)	0.0488 (19)	0.0536 (18)	0.0032 (16)	0.0139 (15)	0.0144 (15)

Geometric parameters (Å, º)

O1—C3	1.202 (4)	C14—C15	1.540 (4)
O2—C11	1.433 (4)	C14—C28	1.543 (4)
O2—H2O	0.8200	C15—C16	1.521 (4)
O3—C16	1.209 (3)	C15—H15A	0.9700
O4—C23	1.206 (4)	C15—H15B	0.9700
O5—C24	1.446 (5)	C16—C17	1.515 (4)
O5—H5O	0.8200	C17—C20	1.534 (4)
O6—C25	1.432 (5)	C17—H17	0.9800
O6—H6O	0.8200	C18—H18A	0.9600
C1—C10	1.516 (4)	C18—H18B	0.9600
C1—C2	1.526 (4)	C18—H18C	0.9600
C1—H1A	0.9700	C19—H19A	0.9700
C1—H1B	0.9700	C19—H19B	0.9700
C2—C3	1.497 (5)	C20—C21	1.522 (5)
C2—H2A	0.9700	C20—C22	1.543 (4)
C2—H2B	0.9700	C20—H20	0.9800
C3—C4	1.527 (5)	C21—H21A	0.9600
C4—C30	1.531 (5)	C21—H21B	0.9600
C4—C29	1.538 (5)	C21—H21C	0.9600
C4—C5	1.564 (4)	C22—C23	1.502 (5)
C5—C6	1.518 (4)	C22—H22A	0.9700
C5—C10	1.532 (4)	C22—H22B	0.9700
C5—H5	0.9800	C23—C24	1.514 (5)
C6—C7	1.503 (4)	C24—C25	1.523 (6)
C6—H6A	0.9700	C24—H24	0.9800
C6—H6B	0.9700	C25—C27	1.472 (7)
C7—C8	1.327 (3)	C25—C26	1.503 (5)
C7—H7	0.9300	C26—H26A	0.9600
C8—C9	1.506 (3)	C26—H26B	0.9600
C8—C14	1.508 (3)	C26—H26C	0.9600
C9—C19	1.517 (4)	C27—H27A	0.9600
C9—C10	1.541 (3)	C27—H27B	0.9600
C9—C11	1.548 (3)	C27—H27C	0.9600
C10—C19	1.498 (4)	C28—H28A	0.9600
C11—C12	1.531 (4)	C28—H28B	0.9600
C11—H11	0.9800	C28—H28C	0.9600
C12—C13	1.526 (4)	C29—H29A	0.9600
C12—H12A	0.9700	C29—H29B	0.9600
C12—H12B	0.9700	C29—H29C	0.9600
C13—C18	1.531 (4)	C30—H30A	0.9600
C13—C14	1.559 (4)	C30—H30B	0.9600
C13—C17	1.563 (4)	C30—H30C	0.9600
C11—O2—H2O	109.5	O3—C16—C17	126.3 (2)
C24—O5—H5O	109.5	O3—C16—C15	123.2 (3)
C25—O6—H6O	109.5	C17—C16—C15	110.5 (2)
C10—C1—C2	110.8 (3)	C16—C17—C20	115.0 (2)
C10—C1—H1A	109.5	C16—C17—C13	101.4 (2)
C2—C1—H1A	109.5	C20—C17—C13	120.7 (2)
C10—C1—H1B	109.5	C16—C17—H17	106.2
C2—C1—H1B	109.5	C20—C17—H17	106.2
H1A—C1—H1B	108.1	C13—C17—H17	106.2
C3—C2—C1	110.3 (3)	C13—C18—H18A	109.5
C3—C2—H2A	109.6	C13—C18—H18B	109.5
C1—C2—H2A	109.6	H18A—C18—H18B	109.5
C3—C2—H2B	109.6	C13—C18—H18C	109.5
C1—C2—H2B	109.6	H18A—C18—H18C	109.5
H2A—C2—H2B	108.1	H18B—C18—H18C	109.5
O1—C3—C2	122.1 (3)	C10—C19—C9	61.49 (18)
O1—C3—C4	122.2 (4)	C10—C19—H19A	117.6
C2—C3—C4	115.6 (3)	C9—C19—H19A	117.6
C3—C4—C30	106.5 (3)	C10—C19—H19B	117.6
C3—C4—C29	109.1 (3)	C9—C19—H19B	117.6
C30—C4—C29	109.7 (3)	H19A—C19—H19B	114.7
C3—C4—C5	108.7 (2)	C21—C20—C17	111.9 (3)
C30—C4—C5	112.1 (3)	C21—C20—C22	110.0 (3)
C29—C4—C5	110.6 (2)	C17—C20—C22	110.4 (3)
C6—C5—C10	112.9 (2)	C21—C20—H20	108.1
C6—C5—C4	111.8 (2)	C17—C20—H20	108.1
C10—C5—C4	112.2 (2)	C22—C20—H20	108.1
C6—C5—H5	106.4	C20—C21—H21A	109.5
C10—C5—H5	106.4	C20—C21—H21B	109.5
C4—C5—H5	106.4	H21A—C21—H21B	109.5
C7—C6—C5	111.2 (2)	C20—C21—H21C	109.5
C7—C6—H6A	109.4	H21A—C21—H21C	109.5
C5—C6—H6A	109.4	H21B—C21—H21C	109.5
C7—C6—H6B	109.4	C23—C22—C20	115.2 (3)
C5—C6—H6B	109.4	C23—C22—H22A	108.5
H6A—C6—H6B	108.0	C20—C22—H22A	108.5
C8—C7—C6	124.0 (2)	C23—C22—H22B	108.5
C8—C7—H7	118.0	C20—C22—H22B	108.5
C6—C7—H7	118.0	H22A—C22—H22B	107.5
C7—C8—C9	121.4 (2)	O4—C23—C22	121.9 (3)
C7—C8—C14	121.5 (2)	O4—C23—C24	117.8 (4)
C9—C8—C14	116.9 (2)	C22—C23—C24	120.3 (3)
C8—C9—C19	116.8 (2)	O5—C24—C23	108.6 (3)
C8—C9—C10	115.0 (2)	O5—C24—C25	105.8 (3)
C19—C9—C10	58.65 (18)	C23—C24—C25	116.8 (3)
C8—C9—C11	116.7 (2)	O5—C24—H24	108.4
C19—C9—C11	117.8 (2)	C23—C24—H24	108.4
C10—C9—C11	119.4 (2)	C25—C24—H24	108.4
C19—C10—C1	119.5 (3)	O6—C25—C27	108.0 (5)
C19—C10—C5	119.8 (2)	O6—C25—C26	108.0 (4)
C1—C10—C5	112.5 (2)	C27—C25—C26	112.0 (4)
C19—C10—C9	59.86 (18)	O6—C25—C24	103.8 (3)
C1—C10—C9	118.4 (2)	C27—C25—C24	113.4 (4)
C5—C10—C9	117.2 (2)	C26—C25—C24	111.1 (4)
O2—C11—C12	108.9 (2)	C25—C26—H26A	109.5
O2—C11—C9	108.4 (2)	C25—C26—H26B	109.5
C12—C11—C9	116.3 (2)	H26A—C26—H26B	109.5
O2—C11—H11	107.6	C25—C26—H26C	109.5
C12—C11—H11	107.6	H26A—C26—H26C	109.5
C9—C11—H11	107.6	H26B—C26—H26C	109.5
C13—C12—C11	115.7 (2)	C25—C27—H27A	109.5
C13—C12—H12A	108.3	C25—C27—H27B	109.5
C11—C12—H12A	108.3	H27A—C27—H27B	109.5
C13—C12—H12B	108.3	C25—C27—H27C	109.5
C11—C12—H12B	108.3	H27A—C27—H27C	109.5
H12A—C12—H12B	107.4	H27B—C27—H27C	109.5
C12—C13—C18	109.7 (3)	C14—C28—H28A	109.5
C12—C13—C14	107.7 (2)	C14—C28—H28B	109.5
C18—C13—C14	111.0 (2)	H28A—C28—H28B	109.5
C12—C13—C17	117.3 (2)	C14—C28—H28C	109.5
C18—C13—C17	109.5 (2)	H28A—C28—H28C	109.5
C14—C13—C17	101.4 (2)	H28B—C28—H28C	109.5
C8—C14—C15	116.2 (2)	C4—C29—H29A	109.5
C8—C14—C28	106.9 (2)	C4—C29—H29B	109.5
C15—C14—C28	108.2 (3)	H29A—C29—H29B	109.5
C8—C14—C13	109.9 (2)	C4—C29—H29C	109.5
C15—C14—C13	102.7 (2)	H29A—C29—H29C	109.5
C28—C14—C13	113.2 (2)	H29B—C29—H29C	109.5
C16—C15—C14	103.4 (2)	C4—C30—H30A	109.5
C16—C15—H15A	111.1	C4—C30—H30B	109.5
C14—C15—H15A	111.1	H30A—C30—H30B	109.5
C16—C15—H15B	111.1	C4—C30—H30C	109.5
C14—C15—H15B	111.1	H30A—C30—H30C	109.5
H15A—C15—H15B	109.0	H30B—C30—H30C	109.5
C10—C1—C2—C3	−55.6 (4)	C11—C12—C13—C17	159.5 (3)
C1—C2—C3—O1	−124.5 (4)	C7—C8—C14—C15	−29.4 (4)
C1—C2—C3—C4	56.3 (4)	C9—C8—C14—C15	155.1 (3)
O1—C3—C4—C30	−111.1 (4)	C7—C8—C14—C28	91.5 (3)
C2—C3—C4—C30	68.1 (3)	C9—C8—C14—C28	−84.0 (3)
O1—C3—C4—C29	7.3 (5)	C7—C8—C14—C13	−145.4 (3)
C2—C3—C4—C29	−173.5 (3)	C9—C8—C14—C13	39.1 (3)
O1—C3—C4—C5	128.0 (4)	C12—C13—C14—C8	−67.0 (3)
C2—C3—C4—C5	−52.8 (4)	C18—C13—C14—C8	53.0 (3)
C3—C4—C5—C6	178.1 (3)	C17—C13—C14—C8	169.3 (2)
C30—C4—C5—C6	60.7 (3)	C12—C13—C14—C15	168.8 (2)
C29—C4—C5—C6	−62.1 (4)	C18—C13—C14—C15	−71.2 (3)
C3—C4—C5—C10	50.0 (3)	C17—C13—C14—C15	45.1 (3)
C30—C4—C5—C10	−67.4 (3)	C12—C13—C14—C28	52.3 (3)
C29—C4—C5—C10	169.8 (3)	C18—C13—C14—C28	172.4 (3)
C10—C5—C6—C7	−47.7 (4)	C17—C13—C14—C28	−71.4 (3)
C4—C5—C6—C7	−175.4 (3)	C8—C14—C15—C16	−151.8 (3)
C5—C6—C7—C8	28.7 (5)	C28—C14—C15—C16	88.1 (3)
C6—C7—C8—C9	5.9 (5)	C13—C14—C15—C16	−31.8 (3)
C6—C7—C8—C14	−169.5 (3)	C14—C15—C16—O3	−176.1 (3)
C7—C8—C9—C19	46.9 (4)	C14—C15—C16—C17	6.7 (4)
C14—C8—C9—C19	−137.6 (2)	O3—C16—C17—C20	−24.1 (5)
C7—C8—C9—C10	−19.1 (4)	C15—C16—C17—C20	153.0 (3)
C14—C8—C9—C10	156.5 (2)	O3—C16—C17—C13	−156.1 (3)
C7—C8—C9—C11	−166.3 (3)	C15—C16—C17—C13	21.0 (3)
C14—C8—C9—C11	9.3 (4)	C12—C13—C17—C16	−156.8 (3)
C2—C1—C10—C19	−92.7 (3)	C18—C13—C17—C16	77.5 (3)
C2—C1—C10—C5	55.9 (4)	C14—C13—C17—C16	−39.9 (3)
C2—C1—C10—C9	−162.2 (3)	C12—C13—C17—C20	74.9 (4)
C6—C5—C10—C19	−33.0 (3)	C18—C13—C17—C20	−50.9 (3)
C4—C5—C10—C19	94.5 (3)	C14—C13—C17—C20	−168.2 (3)
C6—C5—C10—C1	178.6 (3)	C1—C10—C19—C9	−107.7 (3)
C4—C5—C10—C1	−53.9 (3)	C5—C10—C19—C9	106.1 (2)
C6—C5—C10—C9	36.2 (4)	C8—C9—C19—C10	−104.3 (2)
C4—C5—C10—C9	163.7 (2)	C11—C9—C19—C10	109.2 (2)
C8—C9—C10—C19	107.3 (3)	C16—C17—C20—C21	−178.3 (3)
C11—C9—C10—C19	−106.4 (3)	C13—C17—C20—C21	−56.3 (4)
C8—C9—C10—C1	−143.2 (3)	C16—C17—C20—C22	58.8 (3)
C19—C9—C10—C1	109.5 (3)	C13—C17—C20—C22	−179.1 (3)
C11—C9—C10—C1	3.0 (4)	C21—C20—C22—C23	123.4 (3)
C8—C9—C10—C5	−3.1 (4)	C17—C20—C22—C23	−112.6 (3)
C19—C9—C10—C5	−110.4 (3)	C20—C22—C23—O4	−22.6 (5)
C11—C9—C10—C5	143.2 (3)	C20—C22—C23—C24	158.6 (3)
C8—C9—C11—O2	−153.7 (2)	O4—C23—C24—O5	2.3 (5)
C19—C9—C11—O2	−7.2 (3)	C22—C23—C24—O5	−178.9 (3)
C10—C9—C11—O2	60.6 (3)	O4—C23—C24—C25	−117.2 (4)
C8—C9—C11—C12	−30.6 (4)	C22—C23—C24—C25	61.6 (5)
C19—C9—C11—C12	115.9 (3)	O5—C24—C25—O6	177.5 (3)
C10—C9—C11—C12	−176.3 (3)	C23—C24—C25—O6	−61.6 (4)
O2—C11—C12—C13	123.9 (3)	O5—C24—C25—C27	−65.6 (5)
C9—C11—C12—C13	1.1 (4)	C23—C24—C25—C27	55.4 (5)
C11—C12—C13—C18	−74.8 (3)	O5—C24—C25—C26	61.6 (5)
C11—C12—C13—C14	46.1 (4)	C23—C24—C25—C26	−177.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O3^i	0.82	2.03	2.830 (3)	165
O5—H5O···O4	0.82	2.06	2.555 (4)	119
O6—H6O···O2^ii	0.82	2.12	2.908 (4)	161

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