(25R)-Spirost-5-en-3-ol dimeth­yl sulfoxide solvate

In the crystal structure of the title compound, C₂₇H₄₂O₃·C₂H₆OS, inter­molecular O—H...O hydrogen bonds link the hydrox­yl groups with the dimeth­yl sulfoxide solvent mol­ecules.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.063
• wR factor = 0.199
• Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level A
REFI017_ALERT_1_A  _refine_diff_density_max is missing
            Maximum value of final difference map (e A-3).
            The following tests will not be performed
            DIFMN_01,DIFMX_01,DIFMX_02
REFI018_ALERT_1_A  _refine_diff_density_min is missing
            Minimum value of final difference map (e A-3).
            The following tests will not be performed
            DIFMN_01,DIFMN_02,DIFMN_03
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............       0.00 Deg.
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.00
PLAT037_ALERT_1_A _diffrn_reflns_theta_full .......... Not Given .          ?
PLAT038_ALERT_1_A _diffrn_measured_fraction_theta_max  Not Given .          ?
PLAT039_ALERT_1_A _diffrn_measured_fraction_theta_full Not Given .          ?
PLAT095_ALERT_1_A No Residual Density Maximum Given ..............          ?
PLAT096_ALERT_1_A No Residual Density Minimum Given ..............          ?

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.76 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.43 Ratio
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for          S
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          1

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           25.07
           From the CIF: _reflns_number_total               4891
           Count of symmetry unique reflns         2893
           Completeness (_total/calc)            169.06%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1998
           Fraction of Friedel pairs measured     0.691
           Are heavy atom types Z>Si present        yes

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

  10 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
   4 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: RAPID-AUTO (Rigaku, 2000); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1990); software used to prepare material for publication: SHELXL97.

(25R)-spirost-5-en-3-ol dimethyl sulfoxide solvate

Crystal data

C27H42O3·C2H6OS	Dx = 1.163 Mg m^−3
Mr = 492.73	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 15087 reflections
a = 7.4688 (15) Å	θ = 2.1–25.1°
b = 9.6157 (19) Å	µ = 0.15 mm^−1
c = 39.192 (8) Å	T = 293 K
V = 2814.7 (10) Å^3	Needle, colourless
Z = 4	0.55 × 0.12 × 0.08 mm
F(000) = 1080

Data collection

Rigaku R-AXIS RAPID IP diffractometer	4891 independent reflections
Radiation source: fine-focus sealed tube	2574 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.070
Detector resolution: 10.00 pixels mm^-1	θmax = 25.1°, θmin = 2.1°
ω scans	h = −8→8
Absorption correction: empirical (using intensity measurements) (ABSCOR; Higashi, 1995)	k = −11→11
Tmin = 0.923, Tmax = 0.988	l = −45→45
15087 measured reflections

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)] = 0.063	H-atom parameters constrained
wR(F^2) = 0.199	w = 1/[σ^2(Fo^2) + (0.094P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
4891 reflections	Δρmax = 0.43 e Å^−3
308 parameters	Δρmin = −0.26 e Å^−3
0 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.1 (2)

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
S	0.8591 (3)	0.7839 (3)	0.55419 (4)	0.0973 (7)
O1	0.3893 (5)	0.9054 (3)	0.90512 (8)	0.0529 (9)
O2	0.4954 (4)	0.7304 (3)	0.86924 (7)	0.0479 (8)
O3	0.3690 (6)	0.8042 (5)	0.57709 (8)	0.0781 (12)
HO3	0.4703	0.7971	0.5692	0.117*
O4	0.6777 (7)	0.8008 (8)	0.53926 (11)	0.119 (2)
C1	0.1861 (7)	0.8825 (5)	0.66328 (11)	0.0474 (12)
H1A	0.0626	0.8873	0.6708	0.057*
H1B	0.2398	0.9730	0.6671	0.057*
C2	0.1891 (7)	0.8514 (6)	0.62483 (12)	0.0564 (14)
H2A	0.1267	0.7648	0.6204	0.068*
H2B	0.1275	0.9250	0.6126	0.068*
C3	0.3798 (8)	0.8405 (6)	0.61211 (12)	0.0572 (14)
H3	0.4370	0.9319	0.6141	0.069*
C4	0.4858 (7)	0.7366 (5)	0.63273 (12)	0.0540 (13)
H4A	0.4429	0.6438	0.6274	0.065*
H4B	0.6104	0.7416	0.6258	0.065*
C5	0.4753 (6)	0.7579 (5)	0.67079 (11)	0.0426 (11)
C6	0.6195 (7)	0.7645 (5)	0.69025 (12)	0.0498 (12)
H6	0.7299	0.7611	0.6793	0.060*
C7	0.6209 (6)	0.7768 (5)	0.72840 (11)	0.0473 (12)
H7A	0.6628	0.8687	0.7347	0.057*
H7B	0.7041	0.7093	0.7377	0.057*
C8	0.4362 (6)	0.7529 (4)	0.74399 (10)	0.0380 (10)
H8	0.4098	0.6530	0.7437	0.046*
C9	0.2934 (6)	0.8300 (4)	0.72251 (11)	0.0383 (10)
H9	0.3327	0.9271	0.7210	0.046*
C10	0.2853 (6)	0.7742 (4)	0.68510 (10)	0.0375 (10)
C11	0.1073 (6)	0.8323 (6)	0.73975 (11)	0.0491 (12)
H11A	0.0294	0.8945	0.7271	0.059*
H11B	0.0557	0.7398	0.7387	0.059*
C12	0.1140 (7)	0.8794 (5)	0.77726 (11)	0.0489 (12)
H12A	0.1512	0.9760	0.7783	0.059*
H12B	−0.0049	0.8728	0.7871	0.059*
C13	0.2438 (6)	0.7905 (4)	0.79812 (11)	0.0362 (10)
C14	0.4279 (6)	0.8056 (4)	0.78097 (10)	0.0365 (10)
H14	0.4516	0.9057	0.7798	0.044*
C15	0.5581 (6)	0.7478 (6)	0.80756 (11)	0.0480 (12)
H15A	0.5507	0.6473	0.8091	0.058*
H15B	0.6806	0.7748	0.8027	0.058*
C16	0.4879 (6)	0.8181 (5)	0.83978 (11)	0.0423 (11)
H16	0.5535	0.9046	0.8440	0.051*
C17	0.2881 (6)	0.8492 (5)	0.83411 (11)	0.0412 (11)
H17	0.2715	0.9503	0.8337	0.049*
C18	0.1821 (7)	0.6412 (5)	0.79990 (13)	0.0523 (13)
H18A	0.2666	0.5877	0.8129	0.078*
H18B	0.1735	0.6039	0.7772	0.078*
H18C	0.0669	0.6371	0.8107	0.078*
C19	0.1901 (8)	0.6343 (5)	0.68314 (13)	0.0525 (13)
H19A	0.2534	0.5675	0.6968	0.079*
H19B	0.1869	0.6034	0.6599	0.079*
H19C	0.0701	0.6440	0.6916	0.079*
C20	0.1971 (6)	0.7915 (6)	0.86596 (12)	0.0524 (13)
H20	0.1518	0.6988	0.8602	0.063*
C21	0.0382 (9)	0.8766 (8)	0.87911 (14)	0.089 (2)
H21A	−0.0514	0.8828	0.8616	0.134*
H21B	0.0780	0.9683	0.8851	0.134*
H21C	−0.0116	0.8320	0.8989	0.134*
C22	0.3522 (7)	0.7718 (5)	0.89088 (11)	0.0487 (12)
C23	0.3314 (8)	0.6658 (6)	0.91818 (13)	0.0611 (15)
H23A	0.3158	0.5749	0.9079	0.073*
H23B	0.2248	0.6864	0.9314	0.073*
C24	0.4942 (9)	0.6625 (6)	0.94198 (14)	0.0659 (16)
H24A	0.5975	0.6273	0.9297	0.079*
H24B	0.4706	0.6005	0.9610	0.079*
C25	0.5341 (8)	0.8093 (6)	0.95543 (12)	0.0648 (15)
H25	0.4349	0.8386	0.9701	0.078*
C26	0.5465 (9)	0.9083 (6)	0.92569 (13)	0.0615 (15)
H26A	0.5648	1.0019	0.9342	0.074*
H26B	0.6492	0.8837	0.9118	0.074*
C27	0.7049 (10)	0.8098 (9)	0.97619 (17)	0.100 (2)
H27A	0.7257	0.9015	0.9850	0.151*
H27B	0.8035	0.7829	0.9619	0.151*
H27C	0.6938	0.7453	0.9948	0.151*
C28	0.9441 (14)	0.6261 (9)	0.5391 (2)	0.129 (3)
H28A	0.8793	0.5505	0.5493	0.194*
H28B	1.0685	0.6188	0.5449	0.194*
H28C	0.9311	0.6222	0.5147	0.194*
C29	1.0044 (12)	0.8895 (9)	0.5303 (2)	0.105 (3)
H29A	0.9794	0.9855	0.5350	0.157*
H29B	0.9870	0.8718	0.5064	0.157*
H29C	1.1260	0.8690	0.5364	0.157*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S	0.0790 (12)	0.1529 (19)	0.0600 (9)	0.0210 (12)	−0.0027 (9)	−0.0054 (10)
O1	0.068 (3)	0.0420 (18)	0.0490 (18)	0.0041 (17)	0.0057 (19)	0.0064 (15)
O2	0.049 (2)	0.0541 (19)	0.0402 (16)	0.0150 (17)	0.0035 (15)	0.0044 (14)
O3	0.079 (3)	0.112 (3)	0.043 (2)	−0.002 (3)	−0.002 (2)	−0.002 (2)
O4	0.072 (3)	0.207 (6)	0.077 (3)	0.037 (4)	−0.010 (2)	−0.031 (3)
C1	0.047 (3)	0.049 (3)	0.046 (3)	−0.003 (2)	0.001 (2)	0.002 (2)
C2	0.058 (4)	0.059 (3)	0.052 (3)	0.000 (3)	−0.009 (3)	−0.004 (2)
C3	0.068 (4)	0.061 (3)	0.043 (3)	−0.004 (3)	−0.006 (3)	0.007 (2)
C4	0.045 (3)	0.066 (3)	0.050 (3)	0.000 (3)	0.008 (2)	−0.010 (2)
C5	0.037 (3)	0.041 (3)	0.049 (3)	0.001 (2)	−0.001 (2)	0.001 (2)
C6	0.036 (3)	0.060 (3)	0.054 (3)	0.003 (3)	0.016 (2)	0.001 (2)
C7	0.031 (3)	0.059 (3)	0.052 (3)	0.005 (2)	0.004 (2)	−0.001 (2)
C8	0.033 (2)	0.032 (2)	0.049 (3)	0.000 (2)	0.0060 (19)	−0.0012 (19)
C9	0.039 (3)	0.028 (2)	0.047 (2)	−0.001 (2)	0.000 (2)	−0.0046 (18)
C10	0.035 (3)	0.035 (2)	0.042 (2)	−0.004 (2)	0.0019 (19)	−0.0046 (19)
C11	0.032 (3)	0.064 (3)	0.051 (3)	0.012 (3)	0.001 (2)	−0.002 (2)
C12	0.040 (3)	0.055 (3)	0.052 (3)	0.011 (2)	0.010 (2)	0.002 (2)
C13	0.037 (3)	0.029 (2)	0.043 (2)	0.0020 (19)	0.0010 (19)	−0.0004 (19)
C14	0.035 (3)	0.031 (2)	0.043 (2)	−0.001 (2)	0.004 (2)	−0.0001 (18)
C15	0.033 (3)	0.063 (3)	0.047 (3)	0.000 (2)	0.004 (2)	0.004 (2)
C16	0.040 (3)	0.045 (3)	0.042 (2)	−0.002 (2)	0.004 (2)	0.000 (2)
C17	0.047 (3)	0.030 (2)	0.046 (3)	0.004 (2)	0.002 (2)	−0.0039 (19)
C18	0.055 (3)	0.045 (3)	0.056 (3)	−0.009 (2)	0.012 (3)	0.000 (2)
C19	0.057 (4)	0.041 (3)	0.059 (3)	−0.003 (2)	0.007 (3)	−0.011 (2)
C20	0.035 (3)	0.071 (3)	0.050 (3)	0.002 (3)	0.010 (2)	0.007 (3)
C21	0.057 (4)	0.156 (7)	0.055 (3)	0.037 (4)	0.007 (3)	0.019 (4)
C22	0.049 (3)	0.054 (3)	0.043 (2)	−0.003 (2)	0.008 (2)	0.007 (2)
C23	0.071 (4)	0.057 (3)	0.055 (3)	−0.001 (3)	0.009 (3)	0.006 (2)
C24	0.081 (4)	0.060 (3)	0.056 (3)	0.016 (3)	0.003 (3)	0.017 (3)
C25	0.075 (4)	0.080 (4)	0.039 (3)	0.009 (3)	0.001 (3)	−0.003 (3)
C26	0.059 (4)	0.065 (3)	0.060 (3)	−0.001 (3)	0.005 (3)	0.000 (3)
C27	0.096 (6)	0.135 (7)	0.070 (4)	0.014 (5)	−0.014 (4)	0.003 (4)
C28	0.119 (8)	0.107 (6)	0.162 (8)	0.023 (6)	0.037 (6)	0.022 (6)
C29	0.087 (6)	0.116 (6)	0.111 (6)	0.019 (5)	0.009 (5)	0.024 (5)

Geometric parameters (Å, º)

S—O4	1.485 (5)	C13—C17	1.555 (6)
S—C28	1.748 (9)	C14—C15	1.530 (6)
S—C29	1.757 (8)	C14—H14	0.9800
O1—C26	1.424 (7)	C15—C16	1.525 (6)
O1—C22	1.428 (6)	C15—H15A	0.9700
O2—C22	1.422 (6)	C15—H15B	0.9700
O2—C16	1.431 (5)	C16—C17	1.538 (7)
O3—C3	1.419 (6)	C16—H16	0.9800
O3—HO3	0.8200	C17—C20	1.526 (7)
C1—C2	1.536 (6)	C17—H17	0.9800
C1—C10	1.538 (6)	C18—H18A	0.9600
C1—H1A	0.9700	C18—H18B	0.9600
C1—H1B	0.9700	C18—H18C	0.9600
C2—C3	1.513 (8)	C19—H19A	0.9600
C2—H2A	0.9700	C19—H19B	0.9600
C2—H2B	0.9700	C19—H19C	0.9600
C3—C4	1.510 (7)	C20—C22	1.527 (7)
C3—H3	0.9800	C20—C21	1.531 (8)
C4—C5	1.508 (7)	C20—H20	0.9800
C4—H4A	0.9700	C21—H21A	0.9600
C4—H4B	0.9700	C21—H21B	0.9600
C5—C6	1.321 (7)	C21—H21C	0.9600
C5—C10	1.534 (6)	C22—C23	1.485 (7)
C6—C7	1.500 (6)	C23—C24	1.533 (8)
C6—H6	0.9300	C23—H23A	0.9700
C7—C8	1.526 (6)	C23—H23B	0.9700
C7—H7A	0.9700	C24—C25	1.536 (8)
C7—H7B	0.9700	C24—H24A	0.9700
C8—C14	1.536 (6)	C24—H24B	0.9700
C8—C9	1.548 (6)	C25—C26	1.507 (7)
C8—H8	0.9800	C25—C27	1.513 (9)
C9—C11	1.545 (6)	C25—H25	0.9800
C9—C10	1.562 (6)	C26—H26A	0.9700
C9—H9	0.9800	C26—H26B	0.9700
C10—C19	1.523 (6)	C27—H27A	0.9600
C11—C12	1.539 (6)	C27—H27B	0.9600
C11—H11A	0.9700	C27—H27C	0.9600
C11—H11B	0.9700	C28—H28A	0.9600
C12—C13	1.530 (6)	C28—H28B	0.9600
C12—H12A	0.9700	C28—H28C	0.9600
C12—H12B	0.9700	C29—H29A	0.9600
C13—C18	1.510 (7)	C29—H29B	0.9600
C13—C14	1.538 (6)	C29—H29C	0.9600
O4—S—C28	107.0 (5)	C16—C15—H15B	111.6
O4—S—C29	106.9 (4)	C14—C15—H15B	111.6
C28—S—C29	95.6 (4)	H15A—C15—H15B	109.4
C26—O1—C22	113.5 (4)	O2—C16—C15	113.2 (4)
C22—O2—C16	106.7 (3)	O2—C16—C17	105.6 (3)
C3—O3—HO3	109.5	C15—C16—C17	107.5 (4)
C2—C1—C10	114.0 (4)	O2—C16—H16	110.1
C2—C1—H1A	108.8	C15—C16—H16	110.1
C10—C1—H1A	108.8	C17—C16—H16	110.1
C2—C1—H1B	108.8	C20—C17—C16	104.1 (4)
C10—C1—H1B	108.8	C20—C17—C13	121.0 (4)
H1A—C1—H1B	107.6	C16—C17—C13	105.5 (3)
C3—C2—C1	110.5 (4)	C20—C17—H17	108.5
C3—C2—H2A	109.5	C16—C17—H17	108.5
C1—C2—H2A	109.5	C13—C17—H17	108.5
C3—C2—H2B	109.5	C13—C18—H18A	109.5
C1—C2—H2B	109.5	C13—C18—H18B	109.5
H2A—C2—H2B	108.1	H18A—C18—H18B	109.5
O3—C3—C4	112.6 (5)	C13—C18—H18C	109.5
O3—C3—C2	106.4 (4)	H18A—C18—H18C	109.5
C4—C3—C2	111.3 (4)	H18B—C18—H18C	109.5
O3—C3—H3	108.8	C10—C19—H19A	109.5
C4—C3—H3	108.8	C10—C19—H19B	109.5
C2—C3—H3	108.8	H19A—C19—H19B	109.5
C5—C4—C3	114.3 (4)	C10—C19—H19C	109.5
C5—C4—H4A	108.7	H19A—C19—H19C	109.5
C3—C4—H4A	108.7	H19B—C19—H19C	109.5
C5—C4—H4B	108.7	C22—C20—C17	103.4 (4)
C3—C4—H4B	108.7	C22—C20—C21	116.1 (4)
H4A—C4—H4B	107.6	C17—C20—C21	115.2 (5)
C6—C5—C4	122.3 (4)	C22—C20—H20	107.2
C6—C5—C10	122.6 (4)	C17—C20—H20	107.2
C4—C5—C10	115.1 (4)	C21—C20—H20	107.2
C5—C6—C7	125.8 (4)	C20—C21—H21A	109.5
C5—C6—H6	117.1	C20—C21—H21B	109.5
C7—C6—H6	117.1	H21A—C21—H21B	109.5
C6—C7—C8	112.4 (4)	C20—C21—H21C	109.5
C6—C7—H7A	109.1	H21A—C21—H21C	109.5
C8—C7—H7A	109.1	H21B—C21—H21C	109.5
C6—C7—H7B	109.1	O2—C22—O1	109.8 (4)
C8—C7—H7B	109.1	O2—C22—C23	108.4 (4)
H7A—C7—H7B	107.9	O1—C22—C23	110.9 (4)
C7—C8—C14	111.4 (4)	O2—C22—C20	102.9 (3)
C7—C8—C9	109.4 (4)	O1—C22—C20	106.6 (4)
C14—C8—C9	109.1 (3)	C23—C22—C20	117.8 (5)
C7—C8—H8	109.0	C22—C23—C24	111.7 (5)
C14—C8—H8	109.0	C22—C23—H23A	109.3
C9—C8—H8	109.0	C24—C23—H23A	109.3
C11—C9—C8	112.9 (4)	C22—C23—H23B	109.3
C11—C9—C10	112.4 (4)	C24—C23—H23B	109.3
C8—C9—C10	111.9 (3)	H23A—C23—H23B	107.9
C11—C9—H9	106.4	C23—C24—C25	110.1 (4)
C8—C9—H9	106.4	C23—C24—H24A	109.6
C10—C9—H9	106.4	C25—C24—H24A	109.6
C19—C10—C5	108.9 (4)	C23—C24—H24B	109.6
C19—C10—C1	110.2 (4)	C25—C24—H24B	109.6
C5—C10—C1	108.2 (4)	H24A—C24—H24B	108.2
C19—C10—C9	111.6 (4)	C26—C25—C27	111.2 (6)
C5—C10—C9	110.1 (4)	C26—C25—C24	109.1 (4)
C1—C10—C9	107.9 (3)	C27—C25—C24	110.5 (6)
C12—C11—C9	113.1 (4)	C26—C25—H25	108.6
C12—C11—H11A	109.0	C27—C25—H25	108.6
C9—C11—H11A	109.0	C24—C25—H25	108.6
C12—C11—H11B	109.0	O1—C26—C25	112.0 (5)
C9—C11—H11B	109.0	O1—C26—H26A	109.2
H11A—C11—H11B	107.8	C25—C26—H26A	109.2
C13—C12—C11	111.5 (4)	O1—C26—H26B	109.2
C13—C12—H12A	109.3	C25—C26—H26B	109.2
C11—C12—H12A	109.3	H26A—C26—H26B	107.9
C13—C12—H12B	109.3	C25—C27—H27A	109.5
C11—C12—H12B	109.3	C25—C27—H27B	109.5
H12A—C12—H12B	108.0	H27A—C27—H27B	109.5
C18—C13—C12	111.3 (4)	C25—C27—H27C	109.5
C18—C13—C14	112.5 (4)	H27A—C27—H27C	109.5
C12—C13—C14	106.3 (4)	H27B—C27—H27C	109.5
C18—C13—C17	111.6 (4)	S—C28—H28A	109.5
C12—C13—C17	114.7 (4)	S—C28—H28B	109.5
C14—C13—C17	99.9 (3)	H28A—C28—H28B	109.5
C15—C14—C8	119.8 (4)	S—C28—H28C	109.5
C15—C14—C13	103.7 (3)	H28A—C28—H28C	109.5
C8—C14—C13	114.7 (4)	H28B—C28—H28C	109.5
C15—C14—H14	105.9	S—C29—H29A	109.5
C8—C14—H14	105.9	S—C29—H29B	109.5
C13—C14—H14	105.9	H29A—C29—H29B	109.5
C16—C15—C14	100.6 (4)	S—C29—H29C	109.5
C16—C15—H15A	111.6	H29A—C29—H29C	109.5
C14—C15—H15A	111.6	H29B—C29—H29C	109.5
C10—C1—C2—C3	−57.5 (6)	C18—C13—C14—C8	60.2 (5)
C1—C2—C3—O3	176.8 (4)	C12—C13—C14—C8	−61.8 (5)
C1—C2—C3—C4	53.8 (6)	C17—C13—C14—C8	178.7 (3)
O3—C3—C4—C5	−170.4 (4)	C8—C14—C15—C16	−174.7 (4)
C2—C3—C4—C5	−51.0 (6)	C13—C14—C15—C16	−45.3 (4)
C3—C4—C5—C6	−129.0 (5)	C22—O2—C16—C15	−150.1 (4)
C3—C4—C5—C10	49.9 (6)	C22—O2—C16—C17	−32.8 (5)
C4—C5—C6—C7	−176.1 (5)	C14—C15—C16—O2	142.4 (4)
C10—C5—C6—C7	5.1 (8)	C14—C15—C16—C17	26.2 (5)
C5—C6—C7—C8	11.2 (7)	O2—C16—C17—C20	9.1 (5)
C6—C7—C8—C14	−163.9 (4)	C15—C16—C17—C20	130.2 (4)
C6—C7—C8—C9	−43.2 (5)	O2—C16—C17—C13	−119.3 (4)
C7—C8—C9—C11	−170.3 (4)	C15—C16—C17—C13	1.8 (5)
C14—C8—C9—C11	−48.2 (5)	C18—C13—C17—C20	−27.1 (6)
C7—C8—C9—C10	61.8 (5)	C12—C13—C17—C20	100.6 (5)
C14—C8—C9—C10	−176.1 (3)	C14—C13—C17—C20	−146.2 (4)
C6—C5—C10—C19	−110.4 (5)	C18—C13—C17—C16	90.4 (4)
C4—C5—C10—C19	70.7 (5)	C12—C13—C17—C16	−142.0 (4)
C6—C5—C10—C1	129.9 (5)	C14—C13—C17—C16	−28.8 (4)
C4—C5—C10—C1	−49.0 (5)	C16—C17—C20—C22	15.7 (5)
C6—C5—C10—C9	12.2 (6)	C13—C17—C20—C22	133.8 (4)
C4—C5—C10—C9	−166.7 (4)	C16—C17—C20—C21	143.4 (5)
C2—C1—C10—C19	−65.6 (5)	C13—C17—C20—C21	−98.5 (6)
C2—C1—C10—C5	53.3 (5)	C16—O2—C22—O1	−70.3 (4)
C2—C1—C10—C9	172.4 (4)	C16—O2—C22—C23	168.5 (4)
C11—C9—C10—C19	−52.3 (5)	C16—O2—C22—C20	42.9 (5)
C8—C9—C10—C19	75.8 (5)	C26—O1—C22—O2	−61.5 (5)
C11—C9—C10—C5	−173.3 (4)	C26—O1—C22—C23	58.3 (5)
C8—C9—C10—C5	−45.1 (5)	C26—O1—C22—C20	−172.3 (4)
C11—C9—C10—C1	68.9 (5)	C17—C20—C22—O2	−35.4 (5)
C8—C9—C10—C1	−163.0 (4)	C21—C20—C22—O2	−162.5 (5)
C8—C9—C11—C12	49.3 (5)	C17—C20—C22—O1	80.1 (4)
C10—C9—C11—C12	176.9 (4)	C21—C20—C22—O1	−47.0 (6)
C9—C11—C12—C13	−55.2 (6)	C17—C20—C22—C23	−154.6 (4)
C11—C12—C13—C18	−64.1 (5)	C21—C20—C22—C23	78.2 (7)
C11—C12—C13—C14	58.7 (5)	O2—C22—C23—C24	66.1 (5)
C11—C12—C13—C17	168.1 (4)	O1—C22—C23—C24	−54.5 (6)
C7—C8—C14—C15	−58.0 (5)	C20—C22—C23—C24	−177.6 (4)
C9—C8—C14—C15	−178.9 (4)	C22—C23—C24—C25	52.6 (6)
C7—C8—C14—C13	177.7 (4)	C23—C24—C25—C26	−51.9 (7)
C9—C8—C14—C13	56.8 (5)	C23—C24—C25—C27	−174.5 (5)
C18—C13—C14—C15	−72.3 (4)	C22—O1—C26—C25	−59.8 (5)
C12—C13—C14—C15	165.7 (4)	C27—C25—C26—O1	177.8 (5)
C17—C13—C14—C15	46.2 (4)	C24—C25—C26—O1	55.6 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—HO3···O4	0.82	1.94	2.741 (7)	164