(3S,4S,5S,10S,13R,14R,17R)-4α,14α-Dimeth­yl-3β-tos­yl-5α-cholest-8-ene-7,11-dione

The stereochemistry as well as the absolute configuration of the title compound, C₃₆H₅₂O₅S, were established and confirmed by single-crystal X-ray diffraction.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.056
• wR factor = 0.156
• Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.81 Ratio

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature         293
PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature ....        293
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.67 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O5     -   C11     ..       6.72 su
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

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           26.04
           From the CIF: _reflns_number_total               6359
           Count of symmetry unique reflns         3711
           Completeness (_total/calc)            171.36%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2648
           Fraction of Friedel pairs measured     0.714
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   6 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
   2 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: KappaCCD Software (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

(3S,4S,5S,10S,13R,14R,17R)-4α,14α-Dimethyl-3β-tosyl-5α-cholest-8-ene- 7,11-dione

Crystal data

C36H52O5S	F(000) = 1296
Mr = 596.84	Dx = 1.180 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 16425 reflections
a = 11.2528 (2) Å	θ = 1.8–26.0°
b = 14.3549 (3) Å	µ = 0.14 mm^−1
c = 20.7998 (5) Å	T = 293 K
V = 3359.85 (12) Å^3	Prism, colorless
Z = 4	0.6 × 0.6 × 0.4 mm

Data collection

Nonius KappaCCD diffractometer	5501 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.049
Graphite monochromator	θmax = 26.0°, θmin = 2.3°
φ scans	h = −12→12
16425 measured reflections	k = −17→17
6358 independent reflections	l = −25→25

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)] = 0.056	H-atom parameters constrained
wR(F^2) = 0.156	w = 1/[σ^2(Fo^2) + (0.0727P)^2 + 1.1094P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.001
6358 reflections	Δρmax = 0.33 e Å^−3
387 parameters	Δρmin = −0.20 e Å^−3
0 restraints	Absolute structure: Flack (1983), 2648 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (11)

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
S1	−0.34928 (8)	0.27052 (6)	0.45602 (4)	0.0705 (2)
O1	−0.4589 (3)	0.3136 (2)	0.44008 (18)	0.1046 (10)
O2	−0.2711 (3)	0.31451 (19)	0.50018 (13)	0.0900 (8)
O3	−0.2827 (2)	0.25184 (19)	0.39099 (11)	0.0788 (7)
O4	0.1665 (2)	0.55830 (14)	0.28805 (16)	0.0874 (8)
O5	0.2402 (3)	0.15287 (18)	0.2676 (2)	0.1261 (13)
C1	0.0397 (3)	0.2103 (2)	0.34645 (17)	0.0650 (8)
H1A	0.0799	0.2325	0.3842	0.078*
H1B	0.0775	0.1543	0.3316	0.078*
C2	−0.0900 (3)	0.1896 (2)	0.36314 (19)	0.0750 (9)
H2A	−0.1286	0.1629	0.3263	0.090*
H2B	−0.0935	0.1466	0.3984	0.090*
C3	−0.1561 (3)	0.2775 (2)	0.38138 (14)	0.0623 (7)
H3	−0.1227	0.3023	0.4203	0.075*
C4	−0.1501 (3)	0.3521 (2)	0.32932 (14)	0.0569 (7)
H4	−0.1855	0.3292	0.2904	0.068*
C5	−0.0183 (2)	0.37157 (18)	0.31708 (13)	0.0483 (6)
H5	0.0125	0.3848	0.3592	0.058*
C6	0.0038 (3)	0.4552 (2)	0.27349 (17)	0.0619 (7)
H6A	−0.0172	0.4389	0.2302	0.074*
H6B	−0.0438	0.5069	0.2874	0.074*
C7	0.1326 (3)	0.47903 (18)	0.27664 (15)	0.0568 (7)
C8	0.2191 (2)	0.40078 (17)	0.27041 (13)	0.0479 (6)
C9	0.1830 (2)	0.31184 (18)	0.28139 (14)	0.0510 (6)
C10	0.0525 (2)	0.28526 (17)	0.29322 (13)	0.0477 (6)
C11	0.2717 (3)	0.2345 (2)	0.2726 (2)	0.0730 (9)
C12	0.4004 (3)	0.2580 (2)	0.25914 (18)	0.0667 (8)
H12A	0.4419	0.2668	0.2990	0.080*
H12B	0.4362	0.2076	0.2357	0.080*
C13	0.4083 (2)	0.34651 (16)	0.21812 (13)	0.0465 (6)
C14	0.3473 (2)	0.42594 (17)	0.25656 (13)	0.0482 (6)
C15	0.3732 (3)	0.5106 (2)	0.21292 (18)	0.0650 (8)
H15A	0.3165	0.5132	0.1785	0.078*
H15B	0.3679	0.5665	0.2381	0.078*
C16	0.5011 (3)	0.4920 (2)	0.18938 (18)	0.0659 (8)
H16A	0.5046	0.5025	0.1438	0.079*
H16B	0.5553	0.5334	0.2107	0.079*
C17	0.5329 (2)	0.38929 (18)	0.20415 (14)	0.0501 (6)
H17	0.5805	0.3870	0.2425	0.060*
C18	0.3453 (3)	0.3276 (2)	0.15386 (16)	0.0665 (8)
H18A	0.3828	0.2760	0.1327	0.080*
H18B	0.3505	0.3819	0.1270	0.080*
H18C	0.2633	0.3131	0.1617	0.080*
C19	0.0047 (3)	0.2487 (2)	0.22885 (15)	0.0662 (8)
H19A	0.0041	0.2983	0.1979	0.079*
H19B	−0.0747	0.2258	0.2347	0.079*
H19C	0.0547	0.1992	0.2137	0.079*
C20	0.6117 (3)	0.3471 (2)	0.15162 (15)	0.0587 (7)
H20	0.5681	0.3501	0.1120	0.070*
C21	0.6441 (3)	0.2454 (2)	0.1662 (2)	0.0767 (9)
H21A	0.7022	0.2241	0.1357	0.092*
H21B	0.5742	0.2073	0.1632	0.092*
H21C	0.6762	0.2411	0.2089	0.092*
C22	0.7234 (3)	0.4059 (3)	0.14298 (16)	0.0675 (8)
H22A	0.7015	0.4699	0.1370	0.081*
H22B	0.7718	0.4002	0.1808	0.081*
C23	0.8045 (3)	0.3806 (3)	0.08596 (17)	0.0756 (10)
H23A	0.8490	0.3255	0.0961	0.091*
H23B	0.7565	0.3694	0.0486	0.091*
C24	0.8924 (4)	0.4583 (4)	0.0708 (2)	0.1006 (14)
H24A	0.8488	0.5117	0.0562	0.121*
H24B	0.9353	0.4739	0.1093	0.121*
C25	0.9862 (5)	0.4355 (5)	0.0187 (3)	0.129 (2)
H25	1.0185	0.4949	0.0068	0.154*
C26	1.0807 (5)	0.3766 (6)	0.0436 (4)	0.177 (3)
H26A	1.0468	0.3252	0.0667	0.213*
H26B	1.1301	0.4123	0.0721	0.213*
H26C	1.1277	0.3536	0.0086	0.213*
C27	0.9317 (6)	0.4055 (5)	−0.0425 (3)	0.148 (2)
H27A	0.9904	0.4068	−0.0759	0.178*
H27B	0.8678	0.4469	−0.0533	0.178*
H27C	0.9015	0.3433	−0.0379	0.178*
C28	−0.2193 (3)	0.4391 (3)	0.3487 (2)	0.0745 (9)
H28A	−0.1821	0.4673	0.3855	0.089*
H28B	−0.2995	0.4222	0.3593	0.089*
H28C	−0.2197	0.4826	0.3136	0.089*
C29	0.4067 (3)	0.4462 (3)	0.32185 (17)	0.0739 (9)
H29A	0.3671	0.4975	0.3423	0.089*
H29B	0.4888	0.4618	0.3151	0.089*
H29C	0.4014	0.3921	0.3488	0.089*
C30	−0.3808 (3)	0.1580 (2)	0.48300 (14)	0.0577 (7)
C31	−0.2943 (3)	0.1091 (3)	0.51723 (18)	0.0771 (9)
H31	−0.2182	0.1370	0.5254	0.092*
C32	−0.3221 (4)	0.0208 (3)	0.53910 (19)	0.0888 (12)
H32	−0.2646	−0.0149	0.5626	0.107*
C33	−0.4320 (5)	−0.0194 (3)	0.52894 (17)	0.0870 (12)
C34	−0.5163 (4)	0.0317 (3)	0.49499 (16)	0.0788 (10)
H34	−0.5929	0.0048	0.4866	0.095*
C35	−0.4906 (3)	0.1199 (2)	0.47204 (15)	0.0642 (8)
H35	−0.5494	0.1558	0.4496	0.077*
C36	−0.4627 (7)	−0.1151 (3)	0.5548 (3)	0.135 (2)
H36A	−0.4200	−0.1616	0.5310	0.162*
H36B	−0.5466	−0.1256	0.5504	0.162*
H36C	−0.4410	−0.1187	0.5994	0.162*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0660 (5)	0.0728 (5)	0.0729 (5)	−0.0038 (4)	0.0168 (4)	0.0072 (4)
O1	0.0800 (18)	0.0876 (18)	0.146 (3)	0.0178 (14)	0.0215 (18)	0.0434 (18)
O2	0.0944 (19)	0.0913 (17)	0.0844 (17)	−0.0265 (15)	0.0249 (14)	−0.0247 (14)
O3	0.0671 (14)	0.1091 (19)	0.0602 (12)	−0.0328 (13)	0.0124 (10)	−0.0017 (13)
O4	0.0682 (14)	0.0422 (11)	0.152 (2)	−0.0009 (10)	0.0191 (15)	−0.0063 (13)
O5	0.111 (2)	0.0566 (15)	0.211 (4)	0.0044 (15)	0.040 (3)	0.006 (2)
C1	0.073 (2)	0.0509 (16)	0.0714 (19)	−0.0045 (14)	0.0052 (16)	0.0131 (14)
C2	0.088 (2)	0.0640 (19)	0.073 (2)	−0.0129 (17)	0.0168 (18)	0.0157 (17)
C3	0.0580 (17)	0.0749 (19)	0.0539 (15)	−0.0173 (16)	0.0045 (13)	0.0033 (14)
C4	0.0501 (15)	0.0676 (17)	0.0531 (15)	−0.0070 (14)	−0.0018 (12)	0.0010 (13)
C5	0.0480 (14)	0.0463 (14)	0.0506 (14)	−0.0041 (11)	−0.0034 (11)	0.0023 (11)
C6	0.0500 (16)	0.0514 (15)	0.084 (2)	0.0039 (12)	0.0000 (14)	0.0125 (14)
C7	0.0514 (16)	0.0403 (13)	0.0788 (19)	0.0009 (11)	0.0071 (14)	0.0070 (13)
C8	0.0467 (14)	0.0393 (12)	0.0576 (15)	0.0000 (10)	0.0014 (12)	0.0030 (11)
C9	0.0512 (15)	0.0406 (12)	0.0612 (16)	0.0021 (11)	0.0000 (12)	0.0030 (12)
C10	0.0540 (15)	0.0367 (13)	0.0523 (14)	−0.0069 (10)	0.0012 (11)	0.0034 (10)
C11	0.0659 (19)	0.0375 (14)	0.116 (3)	0.0023 (13)	0.0108 (18)	0.0198 (16)
C12	0.0593 (18)	0.0443 (15)	0.096 (2)	0.0108 (13)	0.0087 (15)	0.0161 (15)
C13	0.0479 (14)	0.0361 (12)	0.0556 (14)	0.0036 (10)	−0.0037 (11)	0.0017 (11)
C14	0.0454 (14)	0.0414 (12)	0.0577 (15)	−0.0025 (11)	0.0026 (12)	−0.0019 (11)
C15	0.0593 (18)	0.0419 (14)	0.094 (2)	0.0010 (12)	0.0128 (16)	0.0052 (14)
C16	0.0644 (19)	0.0518 (16)	0.081 (2)	−0.0018 (14)	0.0205 (16)	0.0064 (14)
C17	0.0455 (14)	0.0511 (14)	0.0537 (15)	0.0015 (11)	−0.0004 (11)	−0.0011 (12)
C18	0.0570 (18)	0.076 (2)	0.0669 (18)	0.0054 (15)	−0.0100 (15)	−0.0175 (16)
C19	0.071 (2)	0.066 (2)	0.0617 (18)	−0.0163 (15)	0.0077 (15)	−0.0113 (14)
C20	0.0560 (17)	0.0634 (17)	0.0567 (16)	0.0103 (13)	0.0008 (13)	−0.0013 (13)
C21	0.067 (2)	0.0628 (19)	0.101 (3)	0.0124 (16)	0.0078 (18)	−0.0113 (17)
C22	0.0536 (18)	0.086 (2)	0.0626 (18)	0.0009 (15)	0.0095 (14)	0.0006 (17)
C23	0.072 (2)	0.084 (2)	0.071 (2)	0.0198 (18)	0.0130 (17)	0.0000 (18)
C24	0.076 (3)	0.144 (4)	0.082 (2)	0.004 (3)	0.024 (2)	0.015 (3)
C25	0.096 (3)	0.186 (6)	0.103 (4)	0.032 (4)	0.033 (3)	0.028 (4)
C26	0.085 (4)	0.219 (8)	0.228 (8)	0.037 (4)	0.031 (5)	0.075 (7)
C27	0.169 (6)	0.189 (6)	0.088 (3)	0.002 (5)	0.045 (4)	−0.017 (4)
C28	0.0552 (18)	0.078 (2)	0.090 (2)	0.0045 (16)	0.0030 (17)	0.0026 (19)
C29	0.0583 (19)	0.096 (3)	0.068 (2)	−0.0054 (17)	0.0003 (15)	−0.0258 (18)
C30	0.0562 (17)	0.0663 (18)	0.0505 (15)	0.0059 (13)	0.0107 (12)	0.0002 (13)
C31	0.065 (2)	0.090 (2)	0.076 (2)	0.0128 (18)	−0.0030 (17)	0.0030 (19)
C32	0.111 (3)	0.086 (2)	0.069 (2)	0.027 (2)	−0.006 (2)	0.009 (2)
C33	0.141 (4)	0.064 (2)	0.056 (2)	0.007 (2)	0.000 (2)	−0.0028 (16)
C34	0.099 (3)	0.075 (2)	0.0620 (19)	−0.016 (2)	0.0042 (18)	−0.0072 (17)
C35	0.066 (2)	0.074 (2)	0.0522 (16)	−0.0019 (15)	0.0035 (13)	0.0027 (14)
C36	0.225 (7)	0.070 (3)	0.110 (4)	−0.008 (4)	0.008 (4)	0.009 (3)

Geometric parameters (Å, º)

S1—O1	1.419 (3)	C18—H18B	0.9600
S1—O2	1.420 (3)	C18—H18C	0.9600
S1—O3	1.569 (2)	C19—H19A	0.9600
S1—C30	1.746 (3)	C19—H19B	0.9600
O3—C3	1.484 (4)	C19—H19C	0.9600
O4—C7	1.223 (3)	C20—C22	1.524 (4)
O5—C11	1.229 (4)	C20—C21	1.535 (4)
C1—C2	1.529 (5)	C20—H20	0.9598
C1—C10	1.551 (4)	C21—H21A	0.9600
C1—H1A	0.9599	C21—H21B	0.9600
C1—H1B	0.9599	C21—H21C	0.9600
C2—C3	1.513 (5)	C22—C23	1.540 (4)
C2—H2A	0.9600	C22—H22A	0.9601
C2—H2B	0.9600	C22—H22B	0.9600
C3—C4	1.524 (4)	C23—C24	1.523 (6)
C3—H3	0.9601	C23—H23A	0.9599
C4—C28	1.526 (5)	C23—H23B	0.9602
C4—C5	1.531 (4)	C24—C25	1.547 (6)
C4—H4	0.9598	C24—H24A	0.9600
C5—C6	1.525 (4)	C24—H24B	0.9600
C5—C10	1.554 (4)	C25—C26	1.454 (8)
C5—H5	0.9601	C25—C27	1.477 (9)
C6—C7	1.491 (4)	C25—H25	0.9600
C6—H6A	0.9600	C26—H26A	0.9600
C6—H6B	0.9600	C26—H26B	0.9600
C7—C8	1.492 (4)	C26—H26C	0.9600
C8—C9	1.359 (4)	C27—H27A	0.9600
C8—C14	1.514 (4)	C27—H27B	0.9600
C9—C11	1.504 (4)	C27—H27C	0.9600
C9—C10	1.537 (4)	C28—H28A	0.9600
C10—C19	1.535 (4)	C28—H28B	0.9600
C11—C12	1.512 (5)	C28—H28C	0.9600
C12—C13	1.533 (4)	C29—H29A	0.9600
C12—H12A	0.9599	C29—H29B	0.9600
C12—H12B	0.9601	C29—H29C	0.9600
C13—C18	1.536 (4)	C30—C35	1.371 (5)
C13—C14	1.552 (4)	C30—C31	1.395 (5)
C13—C17	1.559 (4)	C31—C32	1.382 (6)
C14—C29	1.541 (4)	C31—H31	0.9601
C14—C15	1.545 (4)	C32—C33	1.382 (6)
C15—C16	1.543 (4)	C32—H32	0.9599
C15—H15A	0.9600	C33—C34	1.392 (6)
C15—H15B	0.9600	C33—C36	1.514 (6)
C16—C17	1.548 (4)	C34—C35	1.384 (5)
C16—H16A	0.9601	C34—H34	0.9599
C16—H16B	0.9599	C35—H35	0.9599
C17—C20	1.532 (4)	C36—H36A	0.9600
C17—H17	0.9601	C36—H36B	0.9600
C18—H18A	0.9600	C36—H36C	0.9600
O1—S1—O2	119.8 (2)	C13—C18—H18A	109.5
O1—S1—O3	106.77 (19)	C13—C18—H18B	109.5
O2—S1—O3	109.70 (14)	H18A—C18—H18B	109.5
O1—S1—C30	107.53 (16)	C13—C18—H18C	109.5
O2—S1—C30	109.24 (17)	H18A—C18—H18C	109.5
O3—S1—C30	102.45 (14)	H18B—C18—H18C	109.5
C3—O3—S1	122.1 (2)	C10—C19—H19A	109.5
C2—C1—C10	112.7 (3)	C10—C19—H19B	109.5
C2—C1—H1A	109.2	H19A—C19—H19B	109.5
C10—C1—H1A	108.0	C10—C19—H19C	109.5
C2—C1—H1B	109.5	H19A—C19—H19C	109.5
C10—C1—H1B	108.0	H19B—C19—H19C	109.5
H1A—C1—H1B	109.5	C22—C20—C17	110.0 (2)
C3—C2—C1	111.4 (3)	C22—C20—C21	110.8 (3)
C3—C2—H2A	108.1	C17—C20—C21	111.9 (3)
C1—C2—H2A	109.2	C22—C20—H20	107.2
C3—C2—H2B	108.9	C17—C20—H20	107.3
C1—C2—H2B	109.7	C21—C20—H20	109.5
H2A—C2—H2B	109.5	C20—C21—H21A	109.5
O3—C3—C2	107.4 (3)	C20—C21—H21B	109.5
O3—C3—C4	108.2 (3)	H21A—C21—H21B	109.5
C2—C3—C4	112.7 (3)	C20—C21—H21C	109.5
O3—C3—H3	110.7	H21A—C21—H21C	109.5
C2—C3—H3	109.1	H21B—C21—H21C	109.5
C4—C3—H3	108.7	C20—C22—C23	116.7 (3)
C3—C4—C28	111.4 (3)	C20—C22—H22A	109.6
C3—C4—C5	106.8 (2)	C23—C22—H22A	106.1
C28—C4—C5	112.9 (3)	C20—C22—H22B	109.0
C3—C4—H4	109.8	C23—C22—H22B	105.9
C28—C4—H4	106.9	H22A—C22—H22B	109.5
C5—C4—H4	108.9	C24—C23—C22	111.8 (3)
C6—C5—C4	113.6 (2)	C24—C23—H23A	108.1
C6—C5—C10	110.8 (2)	C22—C23—H23A	109.5
C4—C5—C10	113.8 (2)	C24—C23—H23B	108.7
C6—C5—H5	109.1	C22—C23—H23B	109.2
C4—C5—H5	103.5	H23A—C23—H23B	109.5
C10—C5—H5	105.3	C23—C24—C25	115.6 (5)
C7—C6—C5	108.3 (2)	C23—C24—H24A	108.6
C7—C6—H6A	109.6	C25—C24—H24A	107.2
C5—C6—H6A	109.0	C23—C24—H24B	109.0
C7—C6—H6B	110.6	C25—C24—H24B	106.8
C5—C6—H6B	109.8	H24A—C24—H24B	109.5
H6A—C6—H6B	109.5	C26—C25—C27	116.2 (7)
O4—C7—C6	121.7 (3)	C26—C25—C24	111.9 (5)
O4—C7—C8	120.9 (3)	C27—C25—C24	112.5 (5)
C6—C7—C8	117.2 (2)	C26—C25—H25	109.3
C9—C8—C7	119.8 (2)	C27—C25—H25	101.2
C9—C8—C14	122.7 (2)	C24—C25—H25	104.5
C7—C8—C14	117.3 (2)	C25—C26—H26A	109.5
C8—C9—C11	118.3 (2)	C25—C26—H26B	109.5
C8—C9—C10	123.1 (2)	H26A—C26—H26B	109.5
C11—C9—C10	118.1 (2)	C25—C26—H26C	109.5
C19—C10—C9	106.3 (2)	H26A—C26—H26C	109.5
C19—C10—C1	110.6 (2)	H26B—C26—H26C	109.5
C9—C10—C1	112.0 (2)	C25—C27—H27A	109.5
C19—C10—C5	111.8 (2)	C25—C27—H27B	109.5
C9—C10—C5	110.1 (2)	H27A—C27—H27B	109.5
C1—C10—C5	106.1 (2)	C25—C27—H27C	109.5
O5—C11—C9	121.5 (3)	H27A—C27—H27C	109.5
O5—C11—C12	118.3 (3)	H27B—C27—H27C	109.5
C9—C11—C12	119.5 (2)	C4—C28—H28A	109.5
C11—C12—C13	110.1 (2)	C4—C28—H28B	109.5
C11—C12—H12A	109.6	H28A—C28—H28B	109.5
C13—C12—H12A	110.0	C4—C28—H28C	109.5
C11—C12—H12B	109.2	H28A—C28—H28C	109.5
C13—C12—H12B	108.5	H28B—C28—H28C	109.5
H12A—C12—H12B	109.5	C14—C29—H29A	109.5
C12—C13—C18	108.1 (2)	C14—C29—H29B	109.5
C12—C13—C14	107.3 (2)	H29A—C29—H29B	109.5
C18—C13—C14	112.0 (2)	C14—C29—H29C	109.5
C12—C13—C17	118.9 (2)	H29A—C29—H29C	109.5
C18—C13—C17	108.8 (2)	H29B—C29—H29C	109.5
C14—C13—C17	101.8 (2)	C35—C30—C31	120.9 (3)
C8—C14—C29	106.9 (2)	C35—C30—S1	119.9 (2)
C8—C14—C15	118.7 (2)	C31—C30—S1	119.2 (3)
C29—C14—C15	106.6 (3)	C32—C31—C30	118.1 (4)
C8—C14—C13	110.1 (2)	C32—C31—H31	121.7
C29—C14—C13	113.6 (2)	C30—C31—H31	120.1
C15—C14—C13	101.1 (2)	C31—C32—C33	122.4 (4)
C16—C15—C14	103.1 (2)	C31—C32—H32	120.3
C16—C15—H15A	112.9	C33—C32—H32	117.3
C14—C15—H15A	110.0	C32—C33—C34	117.8 (4)
C16—C15—H15B	112.1	C32—C33—C36	121.9 (5)
C14—C15—H15B	109.0	C34—C33—C36	120.2 (5)
H15A—C15—H15B	109.5	C35—C34—C33	121.0 (4)
C15—C16—C17	108.5 (2)	C35—C34—H34	119.5
C15—C16—H16A	108.9	C33—C34—H34	119.4
C17—C16—H16A	109.6	C30—C35—C34	119.8 (3)
C15—C16—H16B	109.8	C30—C35—H35	119.2
C17—C16—H16B	110.5	C34—C35—H35	121.0
H16A—C16—H16B	109.5	C33—C36—H36A	109.5
C20—C17—C16	111.7 (2)	C33—C36—H36B	109.5
C20—C17—C13	119.9 (2)	H36A—C36—H36B	109.5
C16—C17—C13	101.8 (2)	C33—C36—H36C	109.5
C20—C17—H17	104.8	H36A—C36—H36C	109.5
C16—C17—H17	109.0	H36B—C36—H36C	109.5
C13—C17—H17	109.5