(23R,23¹S,25S)-23¹,26-Ep­oxy-23-ethyl­furost-20(22)-en-3β-ol

The title compound, C₂₉H₄₆O₃, is a steroid synthesized through a rearrangement of a sarsasapogenin derivative in acidic medium. The newly formed ring F is a tetra­hydro-2H-pyran heterocycle substituted by two methyl groups placed in equatorial positions. This ring displays a chair conformation, while di­hydro­furan ring E, to which it is bonded, has an envelope conformation. The mol­ecules are associated by weak O—H...O hydrogen bonds to form chains running in the [101] direction in the crystal.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 153 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.043
• wR factor = 0.077
• Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSMU01_ALERT_1_C  The ratio of given/expected absorption coefficient lies
               outside the range 0.99 <> 1.01
            Calculated value of mu =     0.047
            Value of mu given      =     0.048
GOODF01_ALERT_2_C  The least squares goodness of fit parameter lies
            outside the range 0.80 <> 2.00
            Goodness of fit given =      0.702
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections (too) Low ..        49% Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00528 Ang.

Alert level G
PLAT398_ALERT_2_G Deviating  C-O-C   Angle From 120 for O16      .      106.4 Degree
PLAT791_ALERT_4_G Model has Chirality at C3          (Sohnke SpGr)          S Verify
PLAT791_ALERT_4_G Model has Chirality at C5          (Sohnke SpGr)          R Verify
PLAT791_ALERT_4_G Model has Chirality at C8          (Sohnke SpGr)          R Verify
PLAT791_ALERT_4_G Model has Chirality at C9          (Sohnke SpGr)          S Verify
PLAT791_ALERT_4_G Model has Chirality at C10         (Sohnke SpGr)          S Verify
PLAT791_ALERT_4_G Model has Chirality at C13         (Sohnke SpGr)          R Verify
PLAT791_ALERT_4_G Model has Chirality at C14         (Sohnke SpGr)          S Verify
PLAT791_ALERT_4_G Model has Chirality at C16         (Sohnke SpGr)          S Verify
PLAT791_ALERT_4_G Model has Chirality at C17         (Sohnke SpGr)          S Verify
PLAT791_ALERT_4_G Model has Chirality at C23         (Sohnke SpGr)          R Verify
PLAT791_ALERT_4_G Model has Chirality at C25         (Sohnke SpGr)          S Verify
PLAT791_ALERT_4_G Model has Chirality at C27         (Sohnke SpGr)          S Verify
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          2 Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          5 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  16 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
  13 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2018); cell refinement: X-AREA (Stoe & Cie, 2018); data reduction: X-AREA (Stoe & Cie, 2018); program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2020); software used to prepare material for publication: publCIF (Westrip, 2010).

(23R,23¹S,25S)-23¹,26-Epoxy-23-ethylfurost-20(22)-en-3β-ol

Crystal data

C29H46O3	F(000) = 488
Mr = 442.66	Dx = 1.160 Mg m^−3
Monoclinic, P21	Ag Kα radiation, λ = 0.56083 Å
a = 6.3829 (7) Å	Cell parameters from 7481 reflections
b = 12.6897 (8) Å	θ = 2.4–27.7°
c = 15.9539 (17) Å	µ = 0.05 mm^−1
β = 101.308 (8)°	T = 153 K
V = 1267.1 (2) Å^3	Irregular, colourless
Z = 2	0.24 × 0.16 × 0.07 mm

Data collection

Stoe Stadivari diffractometer	4669 independent reflections
Radiation source: Sealed X-ray tube, Axo Astix-f Microfocus source	2283 reflections with I > 2σ(I)
Graded multilayer mirror monochromator	Rint = 0.102
Detector resolution: 5.81 pixels mm^-1	θmax = 20.5°, θmin = 2.4°
ω scans	h = −7→7
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2018)	k = −15→15
Tmin = 0.519, Tmax = 1.000	l = −19→19
15499 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.077	w = 1/[σ^2(Fo^2) + (0.0188P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.70	(Δ/σ)max < 0.001
4669 reflections	Δρmax = 0.16 e Å^−3
298 parameters	Δρmin = −0.17 e Å^−3
1 restraint	Extinction correction: (SHELXL2018; Sheldrick 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 constraints	Extinction coefficient: 0.0100 (10)
Primary atom site location: dual

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.7075 (7)	0.3112 (3)	0.7615 (3)	0.0303 (10)
H1A	0.621334	0.309403	0.806762	0.036*
H1B	0.674723	0.246376	0.726844	0.036*
C2	0.9432 (7)	0.3097 (3)	0.8037 (3)	0.0335 (11)
H2A	0.972593	0.247124	0.841295	0.040*
H2B	1.030808	0.303861	0.759143	0.040*
C3	1.0065 (6)	0.4089 (3)	0.8563 (2)	0.0353 (10)
H3	1.165276	0.410355	0.875704	0.042*
O3	0.9070 (5)	0.4036 (2)	0.93021 (18)	0.0447 (8)
H3A	0.972 (8)	0.449 (3)	0.967 (3)	0.067*
C4	0.9355 (6)	0.5075 (3)	0.8039 (2)	0.0313 (10)
H4A	1.024977	0.515500	0.760204	0.038*
H4B	0.961535	0.569582	0.842168	0.038*
C5	0.7003 (7)	0.5073 (3)	0.7592 (2)	0.0304 (10)
H5	0.612950	0.506869	0.804783	0.036*
C6	0.6443 (7)	0.6089 (3)	0.7069 (3)	0.0369 (12)
H6A	0.487038	0.614593	0.689524	0.044*
H6B	0.695409	0.670465	0.743349	0.044*
C7	0.7433 (7)	0.6119 (3)	0.6272 (2)	0.0332 (11)
H7A	0.900717	0.615808	0.644573	0.040*
H7B	0.693851	0.675862	0.593581	0.040*
C8	0.6827 (6)	0.5142 (3)	0.5712 (2)	0.0257 (9)
H8	0.524350	0.514261	0.550355	0.031*
C9	0.7450 (6)	0.4127 (3)	0.6240 (2)	0.0234 (9)
H9	0.902181	0.417847	0.646833	0.028*
C10	0.6379 (6)	0.4079 (3)	0.7034 (2)	0.0255 (9)
C11	0.7125 (7)	0.3130 (3)	0.5679 (3)	0.0287 (10)
H11A	0.775839	0.252065	0.602689	0.034*
H11B	0.557409	0.299583	0.549940	0.034*
C12	0.8121 (7)	0.3202 (3)	0.4879 (2)	0.0283 (10)
H12A	0.969689	0.322403	0.505309	0.034*
H12B	0.773442	0.256685	0.452232	0.034*
C13	0.7352 (6)	0.4182 (3)	0.4354 (2)	0.0229 (9)
C14	0.7897 (6)	0.5144 (3)	0.4943 (2)	0.0235 (9)
H14	0.947049	0.511511	0.517207	0.028*
C15	0.7515 (7)	0.6089 (3)	0.4321 (2)	0.0314 (11)
H15A	0.597790	0.626844	0.416707	0.038*
H15B	0.832343	0.671696	0.457074	0.038*
C16	0.8341 (7)	0.5686 (3)	0.3548 (2)	0.0288 (10)
H16	0.975553	0.601243	0.352721	0.035*
O16	0.6841 (4)	0.58617 (17)	0.27418 (16)	0.0291 (7)
C17	0.8563 (6)	0.4468 (3)	0.3631 (3)	0.0251 (10)
H17	1.010420	0.427022	0.380546	0.030*
C18	0.4938 (5)	0.4103 (3)	0.3978 (2)	0.0277 (9)
H18A	0.466708	0.349055	0.359841	0.042*
H18B	0.446279	0.474441	0.365412	0.042*
H18C	0.415055	0.402417	0.444388	0.042*
C19	0.3914 (5)	0.4007 (4)	0.6764 (3)	0.0373 (10)
H19A	0.339983	0.455995	0.634456	0.056*
H19B	0.326656	0.410169	0.726717	0.056*
H19C	0.351771	0.331534	0.650887	0.056*
C20	0.7720 (5)	0.4121 (3)	0.2728 (2)	0.0246 (9)
C21	0.7993 (7)	0.3020 (3)	0.2430 (3)	0.0340 (11)
H21A	0.720725	0.253044	0.273020	0.051*
H21B	0.951313	0.283437	0.255138	0.051*
H21C	0.743733	0.297329	0.181338	0.051*
C22	0.6775 (6)	0.4928 (3)	0.2281 (2)	0.0261 (10)
C23	0.5667 (6)	0.5036 (3)	0.1365 (2)	0.0268 (9)
H23	0.585841	0.436189	0.106392	0.032*
C24	0.6676 (6)	0.5930 (3)	0.0927 (2)	0.0300 (10)
H24A	0.662424	0.659391	0.124732	0.036*
H24B	0.819359	0.576203	0.093234	0.036*
C25	0.5498 (7)	0.6076 (3)	0.0008 (3)	0.0338 (10)
H25	0.565143	0.541937	−0.032062	0.041*
C26	0.3142 (7)	0.6251 (3)	0.0011 (3)	0.0381 (12)
H26A	0.297184	0.690286	0.033231	0.046*
H26B	0.235255	0.634484	−0.058357	0.046*
O26	0.2251 (4)	0.53738 (19)	0.03962 (17)	0.0344 (8)
C27	0.3263 (6)	0.5230 (3)	0.1284 (2)	0.0276 (10)
H27	0.304525	0.587849	0.161257	0.033*
C28	0.6418 (7)	0.6999 (3)	−0.0415 (3)	0.0475 (13)
H28A	0.612316	0.765851	−0.014044	0.071*
H28B	0.575716	0.702249	−0.102335	0.071*
H28C	0.796571	0.690815	−0.035290	0.071*
C29	0.2096 (6)	0.4323 (3)	0.1596 (3)	0.0335 (11)
H29A	0.059098	0.451242	0.155687	0.050*
H29B	0.274301	0.416708	0.219255	0.050*
H29C	0.219447	0.370062	0.124274	0.050*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.036 (3)	0.033 (2)	0.022 (2)	−0.002 (2)	0.008 (2)	0.004 (2)
C2	0.037 (3)	0.032 (2)	0.033 (3)	0.002 (2)	0.010 (2)	0.007 (2)
C3	0.031 (2)	0.048 (2)	0.027 (2)	−0.004 (2)	0.005 (2)	0.007 (2)
O3	0.050 (2)	0.0554 (19)	0.0292 (19)	−0.0094 (18)	0.0075 (16)	−0.0026 (17)
C4	0.033 (3)	0.035 (2)	0.024 (2)	−0.004 (2)	0.001 (2)	−0.002 (2)
C5	0.031 (3)	0.032 (2)	0.028 (2)	0.002 (2)	0.007 (2)	0.000 (2)
C6	0.042 (3)	0.032 (2)	0.035 (3)	0.008 (2)	0.004 (2)	−0.006 (2)
C7	0.045 (3)	0.0236 (19)	0.029 (3)	0.005 (2)	0.002 (2)	0.0007 (19)
C8	0.025 (2)	0.0226 (19)	0.026 (2)	0.000 (2)	−0.0029 (19)	−0.003 (2)
C9	0.022 (2)	0.0236 (17)	0.025 (2)	0.004 (2)	0.0046 (18)	0.001 (2)
C10	0.020 (2)	0.031 (2)	0.024 (2)	0.002 (2)	0.0025 (19)	0.001 (2)
C11	0.033 (3)	0.022 (2)	0.030 (2)	0.0007 (19)	0.004 (2)	0.002 (2)
C12	0.030 (3)	0.026 (2)	0.029 (3)	0.0032 (18)	0.007 (2)	0.0023 (19)
C13	0.023 (2)	0.0224 (18)	0.024 (2)	0.002 (2)	0.0064 (18)	0.0032 (19)
C14	0.022 (2)	0.0216 (18)	0.025 (2)	−0.0012 (19)	0.0010 (19)	0.004 (2)
C15	0.040 (3)	0.0238 (19)	0.029 (3)	−0.004 (2)	0.001 (2)	0.0005 (19)
C16	0.030 (3)	0.026 (2)	0.027 (2)	−0.0041 (18)	−0.003 (2)	0.0039 (19)
O16	0.0371 (18)	0.0245 (14)	0.0235 (16)	0.0008 (13)	0.0006 (14)	0.0011 (12)
C17	0.015 (2)	0.028 (2)	0.032 (3)	0.0028 (16)	0.004 (2)	0.0017 (18)
C18	0.028 (2)	0.0282 (18)	0.026 (2)	0.000 (2)	0.0025 (18)	−0.001 (2)
C19	0.025 (2)	0.049 (2)	0.039 (3)	0.001 (2)	0.009 (2)	−0.004 (2)
C20	0.022 (2)	0.0290 (19)	0.025 (2)	−0.001 (2)	0.0094 (18)	0.001 (2)
C21	0.042 (3)	0.031 (2)	0.031 (3)	0.004 (2)	0.010 (2)	0.003 (2)
C22	0.024 (2)	0.029 (2)	0.027 (2)	−0.0041 (19)	0.008 (2)	−0.0045 (19)
C23	0.028 (2)	0.0256 (19)	0.026 (2)	0.000 (2)	0.0030 (19)	0.000 (2)
C24	0.030 (3)	0.033 (2)	0.027 (2)	−0.0035 (19)	0.006 (2)	0.0073 (19)
C25	0.037 (3)	0.035 (2)	0.028 (2)	−0.005 (2)	0.003 (2)	0.006 (2)
C26	0.037 (3)	0.043 (2)	0.030 (3)	0.001 (2)	−0.005 (2)	0.009 (2)
O26	0.0336 (18)	0.0410 (17)	0.0252 (17)	−0.0081 (14)	−0.0027 (14)	0.0052 (13)
C27	0.025 (2)	0.034 (2)	0.022 (2)	0.0020 (19)	0.0002 (19)	−0.0017 (19)
C28	0.050 (4)	0.056 (3)	0.036 (3)	−0.006 (3)	0.008 (3)	0.014 (2)
C29	0.030 (3)	0.043 (3)	0.029 (2)	−0.002 (2)	0.010 (2)	0.003 (2)

Geometric parameters (Å, º)

C1—C2	1.523 (5)	C15—H15A	0.9900
C1—C10	1.551 (5)	C15—H15B	0.9900
C1—H1A	0.9900	C16—O16	1.462 (4)
C1—H1B	0.9900	C16—C17	1.556 (4)
C2—C3	1.523 (5)	C16—H16	1.0000
C2—H2A	0.9900	O16—C22	1.391 (4)
C2—H2B	0.9900	C17—C20	1.501 (5)
C3—O3	1.446 (4)	C17—H17	1.0000
C3—C4	1.524 (5)	C18—H18A	0.9800
C3—H3	1.0000	C18—H18B	0.9800
O3—H3A	0.87 (4)	C18—H18C	0.9800
C4—C5	1.531 (5)	C19—H19A	0.9800
C4—H4A	0.9900	C19—H19B	0.9800
C4—H4B	0.9900	C19—H19C	0.9800
C5—C6	1.539 (5)	C20—C22	1.324 (5)
C5—C10	1.550 (5)	C20—C21	1.498 (5)
C5—H5	1.0000	C21—H21A	0.9800
C6—C7	1.527 (5)	C21—H21B	0.9800
C6—H6A	0.9900	C21—H21C	0.9800
C6—H6B	0.9900	C22—C23	1.500 (5)
C7—C8	1.532 (5)	C23—C27	1.535 (5)
C7—H7A	0.9900	C23—C24	1.538 (5)
C7—H7B	0.9900	C23—H23	1.0000
C8—C14	1.517 (5)	C24—C25	1.522 (5)
C8—C9	1.548 (5)	C24—H24A	0.9900
C8—H8	1.0000	C24—H24B	0.9900
C9—C11	1.540 (5)	C25—C26	1.521 (5)
C9—C10	1.554 (5)	C25—C28	1.525 (5)
C9—H9	1.0000	C25—H25	1.0000
C10—C19	1.550 (5)	C26—O26	1.441 (4)
C11—C12	1.537 (5)	C26—H26A	0.9900
C11—H11A	0.9900	C26—H26B	0.9900
C11—H11B	0.9900	O26—C27	1.449 (4)
C12—C13	1.525 (5)	C27—C29	1.507 (5)
C12—H12A	0.9900	C27—H27	1.0000
C12—H12B	0.9900	C28—H28A	0.9800
C13—C14	1.538 (5)	C28—H28B	0.9800
C13—C18	1.543 (5)	C28—H28C	0.9800
C13—C17	1.552 (5)	C29—H29A	0.9800
C14—C15	1.545 (5)	C29—H29B	0.9800
C14—H14	1.0000	C29—H29C	0.9800
C15—C16	1.521 (5)
C2—C1—C10	114.6 (3)	C16—C15—H15A	111.2
C2—C1—H1A	108.6	C14—C15—H15A	111.2
C10—C1—H1A	108.6	C16—C15—H15B	111.2
C2—C1—H1B	108.6	C14—C15—H15B	111.2
C10—C1—H1B	108.6	H15A—C15—H15B	109.1
H1A—C1—H1B	107.6	O16—C16—C15	113.0 (3)
C3—C2—C1	111.4 (3)	O16—C16—C17	105.0 (3)
C3—C2—H2A	109.3	C15—C16—C17	107.8 (3)
C1—C2—H2A	109.3	O16—C16—H16	110.3
C3—C2—H2B	109.3	C15—C16—H16	110.3
C1—C2—H2B	109.3	C17—C16—H16	110.3
H2A—C2—H2B	108.0	C22—O16—C16	106.4 (3)
O3—C3—C2	107.4 (3)	C20—C17—C13	120.5 (3)
O3—C3—C4	110.7 (3)	C20—C17—C16	101.5 (3)
C2—C3—C4	111.0 (3)	C13—C17—C16	104.2 (3)
O3—C3—H3	109.2	C20—C17—H17	109.9
C2—C3—H3	109.2	C13—C17—H17	109.9
C4—C3—H3	109.2	C16—C17—H17	109.9
C3—O3—H3A	107 (3)	C13—C18—H18A	109.5
C3—C4—C5	114.5 (3)	C13—C18—H18B	109.5
C3—C4—H4A	108.6	H18A—C18—H18B	109.5
C5—C4—H4A	108.6	C13—C18—H18C	109.5
C3—C4—H4B	108.6	H18A—C18—H18C	109.5
C5—C4—H4B	108.6	H18B—C18—H18C	109.5
H4A—C4—H4B	107.6	C10—C19—H19A	109.5
C4—C5—C6	110.7 (3)	C10—C19—H19B	109.5
C4—C5—C10	112.8 (3)	H19A—C19—H19B	109.5
C6—C5—C10	111.4 (3)	C10—C19—H19C	109.5
C4—C5—H5	107.2	H19A—C19—H19C	109.5
C6—C5—H5	107.2	H19B—C19—H19C	109.5
C10—C5—H5	107.2	C22—C20—C21	128.3 (4)
C7—C6—C5	112.4 (3)	C22—C20—C17	109.3 (3)
C7—C6—H6A	109.1	C21—C20—C17	122.4 (3)
C5—C6—H6A	109.1	C20—C21—H21A	109.5
C7—C6—H6B	109.1	C20—C21—H21B	109.5
C5—C6—H6B	109.1	H21A—C21—H21B	109.5
H6A—C6—H6B	107.9	C20—C21—H21C	109.5
C6—C7—C8	111.5 (3)	H21A—C21—H21C	109.5
C6—C7—H7A	109.3	H21B—C21—H21C	109.5
C8—C7—H7A	109.3	C20—C22—O16	114.2 (3)
C6—C7—H7B	109.3	C20—C22—C23	132.4 (4)
C8—C7—H7B	109.3	O16—C22—C23	113.4 (3)
H7A—C7—H7B	108.0	C22—C23—C27	111.7 (3)
C14—C8—C7	111.6 (3)	C22—C23—C24	110.6 (3)
C14—C8—C9	109.5 (3)	C27—C23—C24	110.2 (3)
C7—C8—C9	110.3 (3)	C22—C23—H23	108.1
C14—C8—H8	108.5	C27—C23—H23	108.1
C7—C8—H8	108.5	C24—C23—H23	108.1
C9—C8—H8	108.5	C25—C24—C23	110.9 (3)
C11—C9—C8	112.1 (3)	C25—C24—H24A	109.5
C11—C9—C10	114.2 (3)	C23—C24—H24A	109.5
C8—C9—C10	111.6 (3)	C25—C24—H24B	109.5
C11—C9—H9	106.0	C23—C24—H24B	109.5
C8—C9—H9	106.0	H24A—C24—H24B	108.1
C10—C9—H9	106.0	C26—C25—C24	108.5 (3)
C19—C10—C5	109.9 (3)	C26—C25—C28	110.9 (3)
C19—C10—C1	106.0 (3)	C24—C25—C28	111.1 (3)
C5—C10—C1	106.8 (3)	C26—C25—H25	108.8
C19—C10—C9	111.2 (3)	C24—C25—H25	108.8
C5—C10—C9	109.4 (3)	C28—C25—H25	108.8
C1—C10—C9	113.5 (3)	O26—C26—C25	111.2 (3)
C12—C11—C9	113.7 (3)	O26—C26—H26A	109.4
C12—C11—H11A	108.8	C25—C26—H26A	109.4
C9—C11—H11A	108.8	O26—C26—H26B	109.4
C12—C11—H11B	108.8	C25—C26—H26B	109.4
C9—C11—H11B	108.8	H26A—C26—H26B	108.0
H11A—C11—H11B	107.7	C26—O26—C27	112.1 (3)
C13—C12—C11	111.3 (3)	O26—C27—C29	105.4 (3)
C13—C12—H12A	109.4	O26—C27—C23	110.4 (3)
C11—C12—H12A	109.4	C29—C27—C23	113.6 (3)
C13—C12—H12B	109.4	O26—C27—H27	109.1
C11—C12—H12B	109.4	C29—C27—H27	109.1
H12A—C12—H12B	108.0	C23—C27—H27	109.1
C12—C13—C14	107.6 (3)	C25—C28—H28A	109.5
C12—C13—C18	110.5 (3)	C25—C28—H28B	109.5
C14—C13—C18	112.2 (3)	H28A—C28—H28B	109.5
C12—C13—C17	116.4 (3)	C25—C28—H28C	109.5
C14—C13—C17	100.5 (3)	H28A—C28—H28C	109.5
C18—C13—C17	109.3 (3)	H28B—C28—H28C	109.5
C8—C14—C13	114.1 (3)	C27—C29—H29A	109.5
C8—C14—C15	118.8 (3)	C27—C29—H29B	109.5
C13—C14—C15	103.6 (3)	H29A—C29—H29B	109.5
C8—C14—H14	106.5	C27—C29—H29C	109.5
C13—C14—H14	106.5	H29A—C29—H29C	109.5
C15—C14—H14	106.5	H29B—C29—H29C	109.5
C16—C15—C14	102.9 (3)
C10—C1—C2—C3	56.8 (4)	C18—C13—C14—C15	−70.0 (4)
C1—C2—C3—O3	70.1 (4)	C17—C13—C14—C15	46.1 (4)
C1—C2—C3—C4	−51.1 (4)	C8—C14—C15—C16	−166.3 (3)
O3—C3—C4—C5	−68.4 (4)	C13—C14—C15—C16	−38.5 (4)
C2—C3—C4—C5	50.8 (4)	C14—C15—C16—O16	131.1 (3)
C3—C4—C5—C6	−179.1 (3)	C14—C15—C16—C17	15.5 (4)
C3—C4—C5—C10	−53.6 (5)	C15—C16—O16—C22	−135.1 (3)
C4—C5—C6—C7	71.5 (4)	C17—C16—O16—C22	−17.8 (4)
C10—C5—C6—C7	−54.9 (5)	C12—C13—C17—C20	95.8 (4)
C5—C6—C7—C8	54.7 (4)	C14—C13—C17—C20	−148.4 (3)
C6—C7—C8—C14	−177.2 (3)	C18—C13—C17—C20	−30.2 (5)
C6—C7—C8—C9	−55.3 (4)	C12—C13—C17—C16	−151.3 (3)
C14—C8—C9—C11	−49.8 (4)	C14—C13—C17—C16	−35.5 (4)
C7—C8—C9—C11	−173.0 (4)	C18—C13—C17—C16	82.6 (4)
C14—C8—C9—C10	−179.5 (3)	O16—C16—C17—C20	17.8 (4)
C7—C8—C9—C10	57.4 (4)	C15—C16—C17—C20	138.5 (3)
C4—C5—C10—C19	167.6 (3)	O16—C16—C17—C13	−108.1 (4)
C6—C5—C10—C19	−67.1 (4)	C15—C16—C17—C13	12.7 (4)
C4—C5—C10—C1	53.1 (4)	C13—C17—C20—C22	102.3 (4)
C6—C5—C10—C1	178.3 (4)	C16—C17—C20—C22	−12.0 (4)
C4—C5—C10—C9	−70.1 (4)	C13—C17—C20—C21	−78.2 (5)
C6—C5—C10—C9	55.1 (4)	C16—C17—C20—C21	167.5 (3)
C2—C1—C10—C19	−173.3 (3)	C21—C20—C22—O16	−178.3 (3)
C2—C1—C10—C5	−56.1 (4)	C17—C20—C22—O16	1.2 (5)
C2—C1—C10—C9	64.5 (4)	C21—C20—C22—C23	0.7 (7)
C11—C9—C10—C19	−64.1 (4)	C17—C20—C22—C23	−179.9 (4)
C8—C9—C10—C19	64.5 (4)	C16—O16—C22—C20	11.1 (4)
C11—C9—C10—C5	174.4 (3)	C16—O16—C22—C23	−168.1 (3)
C8—C9—C10—C5	−57.0 (4)	C20—C22—C23—C27	112.5 (5)
C11—C9—C10—C1	55.3 (4)	O16—C22—C23—C27	−68.5 (4)
C8—C9—C10—C1	−176.2 (3)	C20—C22—C23—C24	−124.5 (5)
C8—C9—C11—C12	49.6 (4)	O16—C22—C23—C24	54.5 (4)
C10—C9—C11—C12	177.9 (3)	C22—C23—C24—C25	−177.5 (3)
C9—C11—C12—C13	−53.6 (4)	C27—C23—C24—C25	−53.6 (4)
C11—C12—C13—C14	56.6 (4)	C23—C24—C25—C26	54.9 (4)
C11—C12—C13—C18	−66.2 (4)	C23—C24—C25—C28	177.0 (3)
C11—C12—C13—C17	168.4 (3)	C24—C25—C26—O26	−58.8 (4)
C7—C8—C14—C13	180.0 (3)	C28—C25—C26—O26	179.0 (3)
C9—C8—C14—C13	57.6 (4)	C25—C26—O26—C27	62.2 (4)
C7—C8—C14—C15	−57.3 (4)	C26—O26—C27—C29	177.6 (3)
C9—C8—C14—C15	−179.7 (3)	C26—O26—C27—C23	−59.3 (4)
C12—C13—C14—C8	−61.0 (4)	C22—C23—C27—O26	177.7 (3)
C18—C13—C14—C8	60.7 (4)	C24—C23—C27—O26	54.4 (4)
C17—C13—C14—C8	176.8 (3)	C22—C23—C27—C29	−64.2 (4)
C12—C13—C14—C15	168.3 (3)	C24—C23—C27—C29	172.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O26^i	0.87 (4)	2.11 (4)	2.943 (4)	159 (5)

Symmetry code: (i) x+1, y, z+1.