(10S,13R,14R)-17-(2-Hydr­oxy-1,5-dimethyl­hex-4-en­yl)-4,4,10,13,14-penta­methyl-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetra­deca­hydro-1H-cyclo­penta­[a]phenanthren-3-ol

The title compound, C₃₀H₅₀O₂, was isolated from the wood-rotting fungus Inonotus obliquus. It is a lanostane-type triterpene. There are one cyclo­hexane ring, two cyclohexene rings and one cyclo­pentane ring in the molecule.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.051
• wR factor = 0.139
• Data-to-parameter ratio = 9.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C22

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
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) ...       3.33 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.00 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C15
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT411_ALERT_2_C Short Inter H...H Contact  H3     ..  H18     ..       2.13 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           25.00
           From the CIF: _reflns_number_total               2759
           Count of symmetry unique reflns         2757
           Completeness (_total/calc)            100.07%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         2
           Fraction of Friedel pairs measured     0.001
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   8 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
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXL97.

(10S,13R,14R)-17-(2-Hydroxy-1,5-dimethylhex-4-enyl)-4,4,10,13,14- pentamethyl-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H- cyclopenta[a]phenanthren-3-ol

Crystal data

C30H50O2	Dx = 1.081 Mg m^−3
Mr = 442.70	Melting point = 452.2–454.6 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
a = 7.4504 (11) Å	Cell parameters from 2191 reflections
b = 12.746 (2) Å	θ = 2.8–26.3°
c = 28.639 (6) Å	µ = 0.07 mm^−1
V = 2719.7 (9) Å^3	T = 294 K
Z = 4	Plate, white
F(000) = 984	0.24 × 0.22 × 0.04 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2759 independent reflections
Radiation source: fine-focus sealed tube	1563 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.088
φ and ω scans	θmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.985, Tmax = 0.997	k = −14→15
13212 measured reflections	l = −19→34

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)] = 0.051	H-atom parameters constrained
wR(F^2) = 0.139	w = 1/[σ^2(Fo^2) + (0.0365P)^2 + 1.7113P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
2759 reflections	Δρmax = 0.23 e Å^−3
300 parameters	Δρmin = −0.23 e Å^−3
0 restraints	Extinction correction: SHELXL97
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0026 (5)

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	0.3950 (6)	0.7160 (3)	0.46602 (11)	0.0593 (11)
H1	0.4575	0.7675	0.4714	0.089*
O2	0.3833 (5)	0.3880 (3)	0.01077 (12)	0.0516 (10)
H2	0.2803	0.3687	0.0161	0.077*
C1	0.2239 (7)	0.6574 (4)	0.34481 (16)	0.0498 (15)
H1A	0.2631	0.7229	0.3309	0.060*
H1B	0.1038	0.6428	0.3335	0.060*
C2	0.2178 (7)	0.6703 (5)	0.39802 (16)	0.0519 (15)
H2A	0.1388	0.7281	0.4060	0.062*
H2B	0.1698	0.6070	0.4121	0.062*
C3	0.4033 (7)	0.6914 (4)	0.41720 (16)	0.0461 (14)
H3	0.4468	0.7548	0.4015	0.055*
C4	0.5386 (7)	0.6052 (4)	0.40632 (17)	0.0448 (13)
C5	0.5368 (7)	0.5886 (4)	0.35229 (16)	0.0408 (13)
H5	0.5776	0.6557	0.3393	0.049*
C6	0.6705 (7)	0.5092 (5)	0.33474 (16)	0.0534 (15)
H6A	0.6248	0.4389	0.3398	0.064*
H6B	0.7825	0.5163	0.3517	0.064*
C7	0.7028 (7)	0.5269 (5)	0.28278 (17)	0.0608 (17)
H7A	0.7885	0.5836	0.2790	0.073*
H7B	0.7558	0.4641	0.2696	0.073*
C8	0.5380 (8)	0.5530 (4)	0.25619 (16)	0.0440 (14)
C9	0.3795 (7)	0.5720 (4)	0.27597 (16)	0.0419 (13)
C10	0.3501 (7)	0.5691 (4)	0.32923 (16)	0.0409 (13)
C11	0.2127 (7)	0.5925 (5)	0.24714 (16)	0.0587 (17)
H11A	0.1703	0.6626	0.2544	0.070*
H11B	0.1205	0.5437	0.2572	0.070*
C12	0.2305 (8)	0.5835 (5)	0.19331 (17)	0.0563 (16)
H12A	0.1219	0.5524	0.1808	0.068*
H12B	0.2422	0.6533	0.1801	0.068*
C13	0.3903 (6)	0.5179 (4)	0.17849 (15)	0.0393 (12)
C14	0.5565 (7)	0.5644 (4)	0.20381 (16)	0.0414 (13)
C15	0.7091 (7)	0.5046 (5)	0.17978 (16)	0.0633 (17)
H15A	0.7225	0.4349	0.1929	0.076*
H15B	0.8218	0.5420	0.1829	0.076*
C16	0.6497 (7)	0.4988 (5)	0.12797 (16)	0.0510 (15)
H16A	0.7166	0.5490	0.1094	0.061*
H16B	0.6711	0.4291	0.1156	0.061*
C17	0.4467 (7)	0.5248 (4)	0.12665 (15)	0.0415 (13)
H17	0.4346	0.5982	0.1170	0.050*
C18	0.3481 (7)	0.4575 (4)	0.09054 (15)	0.0432 (13)
H18	0.3721	0.3843	0.0989	0.052*
C19	0.4287 (8)	0.4737 (4)	0.04147 (15)	0.0447 (13)
H19	0.5596	0.4760	0.0445	0.054*
C20	0.3685 (8)	0.5732 (4)	0.01839 (16)	0.0506 (14)
H20A	0.3846	0.6308	0.0401	0.061*
H20B	0.2412	0.5679	0.0117	0.061*
C21	0.4661 (8)	0.5989 (4)	−0.02610 (16)	0.0511 (15)
H21	0.5509	0.5504	−0.0362	0.061*
C22	0.4446 (8)	0.6820 (4)	−0.05214 (18)	0.0522 (15)
C23	0.5539 (9)	0.7037 (5)	−0.09452 (18)	0.0733 (19)
H23A	0.6341	0.7611	−0.0884	0.110*
H23B	0.4760	0.7216	−0.1200	0.110*
H23C	0.6223	0.6424	−0.1025	0.110*
C24	0.3096 (12)	0.7631 (6)	−0.0406 (3)	0.131 (4)
H24A	0.2337	0.7380	−0.0159	0.196*
H24B	0.2380	0.7778	−0.0676	0.196*
H24C	0.3694	0.8260	−0.0306	0.196*
C25	0.5027 (8)	0.5066 (4)	0.43531 (16)	0.0592 (17)
H25A	0.5292	0.5206	0.4675	0.089*
H25B	0.5774	0.4505	0.4243	0.089*
H25C	0.3788	0.4870	0.4323	0.089*
C26	0.7266 (8)	0.6456 (5)	0.42014 (18)	0.0608 (17)
H26A	0.7269	0.6644	0.4526	0.091*
H26B	0.7560	0.7061	0.4017	0.091*
H26C	0.8139	0.5916	0.4148	0.091*
C27	0.2654 (9)	0.4632 (4)	0.34109 (17)	0.0611 (17)
H27A	0.1667	0.4500	0.3204	0.092*
H27B	0.2229	0.4642	0.3727	0.092*
H27C	0.3535	0.4087	0.3376	0.092*
C28	0.3599 (9)	0.4035 (4)	0.19271 (16)	0.0564 (16)
H28A	0.3480	0.3992	0.2260	0.085*
H28B	0.4602	0.3619	0.1828	0.085*
H28C	0.2524	0.3779	0.1782	0.085*
C29	0.5879 (9)	0.6811 (4)	0.19410 (18)	0.072 (2)
H29A	0.4882	0.7210	0.2058	0.108*
H29B	0.5991	0.6921	0.1611	0.108*
H29C	0.6960	0.7035	0.2094	0.108*
C30	0.1447 (7)	0.4696 (5)	0.09006 (18)	0.0555 (15)
H30A	0.0953	0.4394	0.1180	0.083*
H30B	0.0963	0.4342	0.0633	0.083*
H30C	0.1143	0.5427	0.0886	0.083*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.063 (3)	0.065 (3)	0.050 (2)	−0.015 (2)	0.005 (2)	−0.0212 (19)
O2	0.054 (2)	0.055 (2)	0.046 (2)	−0.005 (2)	−0.008 (2)	−0.0089 (19)
C1	0.039 (3)	0.066 (4)	0.045 (3)	0.002 (3)	0.006 (3)	−0.005 (3)
C2	0.043 (3)	0.067 (4)	0.046 (3)	0.001 (3)	0.006 (3)	−0.007 (3)
C3	0.047 (4)	0.053 (3)	0.038 (3)	−0.005 (3)	0.002 (3)	−0.005 (3)
C4	0.041 (3)	0.049 (3)	0.044 (3)	−0.002 (3)	−0.001 (3)	0.002 (3)
C5	0.037 (3)	0.044 (3)	0.042 (3)	0.004 (3)	0.002 (3)	0.003 (3)
C6	0.045 (4)	0.072 (4)	0.043 (3)	0.014 (3)	−0.002 (3)	0.001 (3)
C7	0.042 (4)	0.095 (5)	0.045 (3)	0.009 (4)	−0.003 (3)	−0.004 (3)
C8	0.039 (3)	0.054 (4)	0.038 (3)	−0.001 (3)	−0.002 (3)	−0.001 (3)
C9	0.033 (3)	0.057 (3)	0.036 (3)	−0.001 (3)	−0.001 (3)	0.002 (3)
C10	0.037 (3)	0.045 (3)	0.041 (3)	−0.003 (3)	0.006 (3)	−0.001 (3)
C11	0.040 (3)	0.089 (5)	0.047 (3)	0.012 (3)	−0.004 (3)	−0.004 (3)
C12	0.042 (3)	0.085 (4)	0.042 (3)	0.015 (3)	−0.002 (3)	−0.002 (3)
C13	0.031 (3)	0.049 (3)	0.038 (3)	0.002 (3)	0.002 (2)	0.003 (3)
C14	0.034 (3)	0.054 (3)	0.036 (3)	−0.006 (3)	−0.001 (3)	−0.002 (2)
C15	0.039 (4)	0.103 (5)	0.048 (3)	0.007 (4)	0.003 (3)	−0.013 (4)
C16	0.036 (3)	0.074 (4)	0.042 (3)	−0.004 (3)	0.001 (3)	−0.003 (3)
C17	0.040 (3)	0.048 (3)	0.036 (2)	−0.002 (3)	−0.001 (2)	−0.003 (3)
C18	0.047 (4)	0.047 (3)	0.036 (3)	0.002 (3)	−0.006 (3)	0.001 (2)
C19	0.053 (4)	0.041 (3)	0.039 (3)	0.002 (3)	−0.004 (3)	−0.005 (3)
C20	0.059 (4)	0.051 (3)	0.042 (3)	0.004 (3)	0.001 (3)	0.000 (3)
C21	0.062 (4)	0.046 (3)	0.046 (3)	0.004 (3)	0.007 (3)	−0.004 (3)
C22	0.063 (4)	0.047 (3)	0.047 (3)	0.000 (3)	0.008 (3)	0.000 (3)
C23	0.095 (5)	0.063 (4)	0.061 (4)	−0.013 (4)	0.013 (4)	−0.001 (3)
C24	0.162 (9)	0.101 (6)	0.130 (7)	0.067 (6)	0.071 (7)	0.060 (5)
C25	0.077 (5)	0.057 (4)	0.044 (3)	−0.001 (4)	0.000 (3)	0.006 (3)
C26	0.050 (4)	0.078 (4)	0.053 (3)	0.002 (4)	−0.008 (3)	−0.008 (3)
C27	0.073 (4)	0.062 (4)	0.049 (3)	−0.020 (4)	0.011 (3)	−0.004 (3)
C28	0.073 (4)	0.054 (3)	0.042 (3)	−0.013 (3)	0.001 (3)	0.004 (3)
C29	0.092 (5)	0.075 (4)	0.050 (3)	−0.032 (4)	0.001 (4)	−0.002 (3)
C30	0.036 (3)	0.077 (4)	0.054 (3)	−0.006 (3)	−0.007 (3)	0.000 (3)

Geometric parameters (Å, º)

O1—C3	1.434 (5)	C15—H15B	0.9700
O1—H1	0.8200	C16—C17	1.549 (7)
O2—C19	1.442 (5)	C16—H16A	0.9700
O2—H2	0.8200	C16—H16B	0.9700
C1—C2	1.533 (6)	C17—C18	1.531 (6)
C1—C10	1.534 (7)	C17—H17	0.9800
C1—H1A	0.9700	C18—C30	1.524 (7)
C1—H1B	0.9700	C18—C19	1.542 (6)
C2—C3	1.512 (7)	C18—H18	0.9800
C2—H2A	0.9700	C19—C20	1.500 (6)
C2—H2B	0.9700	C19—H19	0.9800
C3—C4	1.524 (7)	C20—C21	1.503 (7)
C3—H3	0.9800	C20—H20A	0.9700
C4—C25	1.529 (7)	C20—H20B	0.9700
C4—C26	1.544 (8)	C21—C22	1.305 (7)
C4—C5	1.562 (6)	C21—H21	0.9300
C5—C6	1.507 (7)	C22—C24	1.480 (8)
C5—C10	1.560 (7)	C22—C23	1.487 (7)
C5—H5	0.9800	C23—H23A	0.9600
C6—C7	1.524 (6)	C23—H23B	0.9600
C6—H6A	0.9700	C23—H23C	0.9600
C6—H6B	0.9700	C24—H24A	0.9600
C7—C8	1.482 (7)	C24—H24B	0.9600
C7—H7A	0.9700	C24—H24C	0.9600
C7—H7B	0.9700	C25—H25A	0.9600
C8—C9	1.332 (7)	C25—H25B	0.9600
C8—C14	1.514 (6)	C25—H25C	0.9600
C9—C11	1.515 (7)	C26—H26A	0.9600
C9—C10	1.541 (6)	C26—H26B	0.9600
C10—C27	1.529 (7)	C26—H26C	0.9600
C11—C12	1.552 (6)	C27—H27A	0.9600
C11—H11A	0.9700	C27—H27B	0.9600
C11—H11B	0.9700	C27—H27C	0.9600
C12—C13	1.515 (7)	C28—H28A	0.9600
C12—H12A	0.9700	C28—H28B	0.9600
C12—H12B	0.9700	C28—H28C	0.9600
C13—C28	1.531 (7)	C29—H29A	0.9600
C13—C17	1.545 (6)	C29—H29B	0.9600
C13—C14	1.552 (7)	C29—H29C	0.9600
C14—C15	1.532 (7)	C30—H30A	0.9600
C14—C29	1.532 (7)	C30—H30B	0.9600
C15—C16	1.550 (6)	C30—H30C	0.9600
C15—H15A	0.9700
C3—O1—H1	109.5	H15A—C15—H15B	109.0
C19—O2—H2	109.5	C17—C16—C15	107.0 (4)
C2—C1—C10	112.7 (4)	C17—C16—H16A	110.3
C2—C1—H1A	109.1	C15—C16—H16A	110.3
C10—C1—H1A	109.1	C17—C16—H16B	110.3
C2—C1—H1B	109.1	C15—C16—H16B	110.3
C10—C1—H1B	109.1	H16A—C16—H16B	108.6
H1A—C1—H1B	107.8	C18—C17—C13	119.1 (4)
C3—C2—C1	110.7 (4)	C18—C17—C16	111.4 (4)
C3—C2—H2A	109.5	C13—C17—C16	103.3 (4)
C1—C2—H2A	109.5	C18—C17—H17	107.5
C3—C2—H2B	109.5	C13—C17—H17	107.5
C1—C2—H2B	109.5	C16—C17—H17	107.5
H2A—C2—H2B	108.1	C30—C18—C17	115.2 (4)
O1—C3—C2	110.7 (4)	C30—C18—C19	111.4 (4)
O1—C3—C4	112.7 (4)	C17—C18—C19	110.7 (4)
C2—C3—C4	113.7 (4)	C30—C18—H18	106.3
O1—C3—H3	106.4	C17—C18—H18	106.3
C2—C3—H3	106.4	C19—C18—H18	106.3
C4—C3—H3	106.4	O2—C19—C20	107.6 (4)
C3—C4—C25	111.4 (4)	O2—C19—C18	111.3 (4)
C3—C4—C26	107.9 (4)	C20—C19—C18	113.5 (4)
C25—C4—C26	107.1 (5)	O2—C19—H19	108.1
C3—C4—C5	107.1 (4)	C20—C19—H19	108.1
C25—C4—C5	115.2 (4)	C18—C19—H19	108.1
C26—C4—C5	107.9 (4)	C19—C20—C21	114.4 (5)
C6—C5—C10	109.9 (4)	C19—C20—H20A	108.7
C6—C5—C4	114.5 (4)	C21—C20—H20A	108.7
C10—C5—C4	116.7 (4)	C19—C20—H20B	108.7
C6—C5—H5	104.8	C21—C20—H20B	108.7
C10—C5—H5	104.8	H20A—C20—H20B	107.6
C4—C5—H5	104.8	C22—C21—C20	127.0 (5)
C5—C6—C7	109.3 (5)	C22—C21—H21	116.5
C5—C6—H6A	109.8	C20—C21—H21	116.5
C7—C6—H6A	109.8	C21—C22—C24	121.4 (5)
C5—C6—H6B	109.8	C21—C22—C23	123.4 (5)
C7—C6—H6B	109.8	C24—C22—C23	115.2 (5)
H6A—C6—H6B	108.3	C22—C23—H23A	109.5
C8—C7—C6	113.8 (4)	C22—C23—H23B	109.5
C8—C7—H7A	108.8	H23A—C23—H23B	109.5
C6—C7—H7A	108.8	C22—C23—H23C	109.5
C8—C7—H7B	108.8	H23A—C23—H23C	109.5
C6—C7—H7B	108.8	H23B—C23—H23C	109.5
H7A—C7—H7B	107.7	C22—C24—H24A	109.5
C9—C8—C7	123.8 (4)	C22—C24—H24B	109.5
C9—C8—C14	119.0 (5)	H24A—C24—H24B	109.5
C7—C8—C14	117.1 (5)	C22—C24—H24C	109.5
C8—C9—C11	121.8 (4)	H24A—C24—H24C	109.5
C8—C9—C10	122.9 (5)	H24B—C24—H24C	109.5
C11—C9—C10	115.3 (4)	C4—C25—H25A	109.5
C27—C10—C1	109.3 (4)	C4—C25—H25B	109.5
C27—C10—C9	107.4 (4)	H25A—C25—H25B	109.5
C1—C10—C9	110.9 (4)	C4—C25—H25C	109.5
C27—C10—C5	114.5 (4)	H25A—C25—H25C	109.5
C1—C10—C5	107.9 (4)	H25B—C25—H25C	109.5
C9—C10—C5	106.8 (4)	C4—C26—H26A	109.5
C9—C11—C12	117.3 (4)	C4—C26—H26B	109.5
C9—C11—H11A	108.0	H26A—C26—H26B	109.5
C12—C11—H11A	108.0	C4—C26—H26C	109.5
C9—C11—H11B	108.0	H26A—C26—H26C	109.5
C12—C11—H11B	108.0	H26B—C26—H26C	109.5
H11A—C11—H11B	107.2	C10—C27—H27A	109.5
C13—C12—C11	112.7 (4)	C10—C27—H27B	109.5
C13—C12—H12A	109.0	H27A—C27—H27B	109.5
C11—C12—H12A	109.0	C10—C27—H27C	109.5
C13—C12—H12B	109.0	H27A—C27—H27C	109.5
C11—C12—H12B	109.0	H27B—C27—H27C	109.5
H12A—C12—H12B	107.8	C13—C28—H28A	109.5
C12—C13—C28	109.5 (5)	C13—C28—H28B	109.5
C12—C13—C17	116.8 (4)	H28A—C28—H28B	109.5
C28—C13—C17	110.5 (4)	C13—C28—H28C	109.5
C12—C13—C14	106.6 (4)	H28A—C28—H28C	109.5
C28—C13—C14	110.9 (4)	H28B—C28—H28C	109.5
C17—C13—C14	102.2 (4)	C14—C29—H29A	109.5
C8—C14—C15	117.7 (5)	C14—C29—H29B	109.5
C8—C14—C29	106.7 (4)	H29A—C29—H29B	109.5
C15—C14—C29	106.7 (5)	C14—C29—H29C	109.5
C8—C14—C13	110.7 (4)	H29A—C29—H29C	109.5
C15—C14—C13	101.1 (4)	H29B—C29—H29C	109.5
C29—C14—C13	114.1 (4)	C18—C30—H30A	109.5
C14—C15—C16	104.0 (4)	C18—C30—H30B	109.5
C14—C15—H15A	111.0	H30A—C30—H30B	109.5
C16—C15—H15A	111.0	C18—C30—H30C	109.5
C14—C15—H15B	111.0	H30A—C30—H30C	109.5
C16—C15—H15B	111.0	H30B—C30—H30C	109.5
C10—C1—C2—C3	57.7 (6)	C11—C12—C13—C17	−166.2 (5)
C1—C2—C3—O1	173.0 (4)	C11—C12—C13—C14	−52.8 (6)
C1—C2—C3—C4	−58.9 (6)	C9—C8—C14—C15	−157.3 (5)
O1—C3—C4—C25	54.5 (6)	C7—C8—C14—C15	26.2 (7)
C2—C3—C4—C25	−72.5 (6)	C9—C8—C14—C29	82.9 (6)
O1—C3—C4—C26	−62.8 (6)	C7—C8—C14—C29	−93.6 (6)
C2—C3—C4—C26	170.2 (4)	C9—C8—C14—C13	−41.7 (7)
O1—C3—C4—C5	−178.6 (4)	C7—C8—C14—C13	141.8 (5)
C2—C3—C4—C5	54.3 (6)	C12—C13—C14—C8	63.7 (5)
C3—C4—C5—C6	177.1 (4)	C28—C13—C14—C8	−55.5 (5)
C25—C4—C5—C6	−58.3 (6)	C17—C13—C14—C8	−173.2 (4)
C26—C4—C5—C6	61.2 (6)	C12—C13—C14—C15	−170.8 (5)
C3—C4—C5—C10	−52.5 (6)	C28—C13—C14—C15	70.0 (5)
C25—C4—C5—C10	72.1 (6)	C17—C13—C14—C15	−47.7 (5)
C26—C4—C5—C10	−168.3 (4)	C12—C13—C14—C29	−56.6 (5)
C10—C5—C6—C7	66.0 (6)	C28—C13—C14—C29	−175.8 (4)
C4—C5—C6—C7	−160.4 (5)	C17—C13—C14—C29	66.4 (5)
C5—C6—C7—C8	−40.2 (7)	C8—C14—C15—C16	159.7 (5)
C6—C7—C8—C9	7.8 (9)	C29—C14—C15—C16	−80.5 (5)
C6—C7—C8—C14	−175.9 (5)	C13—C14—C15—C16	39.0 (5)
C7—C8—C9—C11	−176.6 (6)	C14—C15—C16—C17	−16.3 (6)
C14—C8—C9—C11	7.1 (8)	C12—C13—C17—C18	−82.8 (6)
C7—C8—C9—C10	0.1 (9)	C28—C13—C17—C18	43.3 (6)
C14—C8—C9—C10	−176.2 (5)	C14—C13—C17—C18	161.4 (4)
C2—C1—C10—C27	72.2 (6)	C12—C13—C17—C16	153.1 (5)
C2—C1—C10—C9	−169.5 (5)	C28—C13—C17—C16	−80.8 (5)
C2—C1—C10—C5	−52.9 (6)	C14—C13—C17—C16	37.3 (5)
C8—C9—C10—C27	−99.8 (6)	C15—C16—C17—C18	−142.2 (5)
C11—C9—C10—C27	77.0 (6)	C15—C16—C17—C13	−13.2 (6)
C8—C9—C10—C1	140.7 (5)	C13—C17—C18—C30	54.1 (7)
C11—C9—C10—C1	−42.4 (6)	C16—C17—C18—C30	174.1 (5)
C8—C9—C10—C5	23.5 (7)	C13—C17—C18—C19	−178.3 (4)
C11—C9—C10—C5	−159.6 (5)	C16—C17—C18—C19	−58.3 (6)
C6—C5—C10—C27	63.0 (5)	C30—C18—C19—O2	−70.1 (6)
C4—C5—C10—C27	−69.6 (6)	C17—C18—C19—O2	160.2 (4)
C6—C5—C10—C1	−175.1 (4)	C30—C18—C19—C20	51.4 (6)
C4—C5—C10—C1	52.4 (6)	C17—C18—C19—C20	−78.3 (6)
C6—C5—C10—C9	−55.8 (5)	O2—C19—C20—C21	−65.2 (6)
C4—C5—C10—C9	171.6 (4)	C18—C19—C20—C21	171.2 (4)
C8—C9—C11—C12	3.8 (9)	C19—C20—C21—C22	−177.5 (5)
C10—C9—C11—C12	−173.1 (5)	C20—C21—C22—C24	−2.0 (10)
C9—C11—C12—C13	21.2 (8)	C20—C21—C22—C23	176.8 (5)
C11—C12—C13—C28	67.3 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.82	2.01	2.825 (5)	175
O2—H2···O1^ii	0.82	2.22	2.775 (5)	125

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