(3S,5S,10S,13S,14S,17S)-Meth­yl 3β-acet­yl-25,26,27-tris­norlanost-8-en-24-oate

The absolute configuration of the title compound, C₃₀H₄₈O₄, was assigned by reference to a known chiral centre. The conformations of the four fused rings constituting the core of the mol­ecule are comparable to those of some other triterpenes from the same family.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.064
• wR factor = 0.173
• Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C27

Alert level C
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) ...       3.20 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.74 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.02 Ratio
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C30 H48 O4

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           28.28
           From the CIF: _reflns_number_total               3793
           Count of symmetry unique reflns         3925
           Completeness (_total/calc)             96.64%
           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
   1 ALERT level B = Potentially serious problem
   7 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
   3 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: KappaCCD Reference Manual (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.

(3S,5S,10S,13S,14S,17S)-Methyl l3β-acetyl-25,26,27-trisnorlanost-8-en-24-oate

Crystal data

C30H48O4	F(000) = 1040
Mr = 472.71	Dx = 1.132 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 27772 reflections
a = 6.4780 (1) Å	θ = 1.3–28.3°
b = 16.3090 (2) Å	µ = 0.07 mm^−1
c = 26.2450 (5) Å	T = 293 K
V = 2772.78 (8) Å^3	Prism, colourless
Z = 4	0.4 × 0.2 × 0.2 mm

Data collection

Nonius KappaCCD diffractometer	2873 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.069
Graphite monochromator	θmax = 28.3°, θmin = 2.9°
0.5° φ and ω scans	h = −8→8
27772 measured reflections	k = −21→21
3793 independent reflections	l = −34→34

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.173	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0752P)^2 + 0.9128P] where P = (Fo^2 + 2Fc^2)/3
3793 reflections	(Δ/σ)max < 0.001
307 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

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	−0.9591 (10)	−0.7830 (4)	−0.0643 (2)	0.195 (3)
O2	−1.2476 (7)	−0.7739 (2)	−0.10553 (18)	0.1212 (13)
O3	−0.8910 (4)	−0.01285 (15)	−0.02307 (10)	0.0712 (7)
O4	−0.5524 (6)	−0.0005 (2)	−0.00886 (13)	0.0965 (10)
C1	−0.9923 (6)	−0.2353 (2)	−0.04859 (11)	0.0553 (8)
H1A	−0.8541	−0.2555	−0.0447	0.066*
H1B	−1.0873	−0.2725	−0.0327	0.066*
C2	−1.0096 (6)	−0.1503 (2)	−0.02395 (13)	0.0623 (9)
H2A	−1.1487	−0.1306	−0.0271	0.075*
H2B	−0.9741	−0.1547	0.0115	0.075*
C3	−0.8672 (6)	−0.09031 (19)	−0.04928 (13)	0.0569 (8)
H3	−0.7275	−0.1093	−0.0460	0.068*
C4	−0.9061 (5)	−0.07931 (19)	−0.10695 (13)	0.0537 (7)
C5	−0.8991 (5)	−0.16676 (19)	−0.13028 (11)	0.0483 (7)
H5	−0.7630	−0.1835	−0.1202	0.058*
C6	−0.9177 (7)	−0.1691 (2)	−0.18834 (12)	0.0629 (9)
H6A	−1.0600	−0.1641	−0.1981	0.076*
H6B	−0.8404	−0.1244	−0.2025	0.076*
C7	−0.8323 (7)	−0.2495 (2)	−0.20759 (12)	0.0633 (9)
H7A	−0.8770	−0.2587	−0.2420	0.076*
H7B	−0.6843	−0.2476	−0.2065	0.076*
C8	−0.8928 (5)	−0.3223 (2)	−0.17646 (11)	0.0486 (7)
C9	−0.9846 (4)	−0.31670 (19)	−0.13077 (11)	0.0455 (6)
C10	−1.0384 (5)	−0.23361 (19)	−0.10646 (11)	0.0470 (7)
C11	−1.0427 (5)	−0.39201 (19)	−0.10012 (12)	0.0543 (8)
H11A	−0.9663	−0.3924	−0.0688	0.065*
H11B	−1.1879	−0.3916	−0.0928	0.065*
C12	−1.0011 (5)	−0.4758 (2)	−0.12464 (13)	0.0550 (8)
H12A	−0.9762	−0.5155	−0.0983	0.066*
H12B	−1.1191	−0.4922	−0.1443	0.066*
C13	−0.8123 (4)	−0.4717 (2)	−0.15927 (11)	0.0482 (7)
C14	−0.8549 (5)	−0.4055 (2)	−0.20036 (11)	0.0504 (7)
C15	−0.6672 (6)	−0.4155 (3)	−0.23554 (14)	0.0676 (10)
H15A	−0.6966	−0.3951	−0.2691	0.081*
H15B	−0.5536	−0.3855	−0.2213	0.081*
C16	−0.6252 (6)	−0.5083 (2)	−0.23536 (14)	0.0680 (10)
H16A	−0.6624	−0.5307	−0.2679	0.082*
H16B	−0.4817	−0.5185	−0.2289	0.082*
C17	−0.7565 (5)	−0.5476 (2)	−0.19222 (12)	0.0561 (8)
H17	−0.8787	−0.5706	−0.2071	0.067*
C18	−0.6228 (5)	−0.4483 (2)	−0.12631 (14)	0.0613 (8)
H18A	−0.6384	−0.3932	−0.1141	0.074*
H18B	−0.4997	−0.4522	−0.1465	0.074*
H18C	−0.6128	−0.4851	−0.0979	0.074*
C19	−1.0489 (6)	−0.4240 (3)	−0.23285 (15)	0.0692 (10)
H19A	−1.1661	−0.4308	−0.2109	0.083*
H19B	−1.0273	−0.4734	−0.2520	0.083*
H19C	−1.0736	−0.3792	−0.2558	0.083*
C20	−1.2734 (5)	−0.2197 (2)	−0.11387 (15)	0.0660 (9)
H20A	−1.3007	−0.2066	−0.1489	0.079*
H20B	−1.3181	−0.1752	−0.0926	0.079*
H20C	−1.3469	−0.2686	−0.1047	0.079*
C21	−0.7280 (6)	−0.0277 (2)	−0.12872 (16)	0.0702 (10)
H21A	−0.7539	−0.0162	−0.1640	0.084*
H21B	−0.6009	−0.0575	−0.1255	0.084*
H21C	−0.7179	0.0229	−0.1102	0.084*
C22	−1.1057 (7)	−0.0321 (2)	−0.11672 (16)	0.0719 (10)
H22A	−1.1484	−0.0403	−0.1514	0.086*
H22B	−1.0828	0.0253	−0.1108	0.086*
H22C	−1.2114	−0.0516	−0.0941	0.086*
C23	−0.6482 (6)	−0.6210 (2)	−0.16800 (15)	0.0691 (10)
H23	−0.5259	−0.5982	−0.1529	0.083*
C24	−0.5825 (8)	−0.6841 (3)	−0.20785 (19)	0.0920 (14)
H24A	−0.7028	−0.7059	−0.2244	0.110*
H24B	−0.5083	−0.7278	−0.1915	0.110*
H24C	−0.4953	−0.6583	−0.2327	0.110*
C25	−0.7625 (7)	−0.6634 (3)	−0.12466 (16)	0.0758 (11)
H25A	−0.6783	−0.7074	−0.1120	0.091*
H25B	−0.7882	−0.6249	−0.0978	0.091*
C26	−0.9664 (8)	−0.7016 (3)	−0.13915 (18)	0.0867 (13)
H26A	−1.0647	−0.6583	−0.1443	0.104*
H26B	−0.9505	−0.7322	−0.1701	0.104*
C27	−1.0520 (9)	−0.7583 (3)	−0.0997 (2)	0.0875 (14)
C28	−1.3446 (11)	−0.8264 (4)	−0.0671 (3)	0.146 (3)
H28A	−1.4265	−0.8676	−0.0836	0.175*
H28B	−1.4313	−0.7936	−0.0455	0.175*
H28C	−1.2396	−0.8523	−0.0469	0.175*
C29	−0.7247 (9)	0.0246 (2)	−0.00402 (15)	0.0759 (12)
C30	−0.7856 (10)	0.1004 (3)	0.02399 (18)	0.1037 (18)
H30A	−0.7709	0.0916	0.0600	0.124*
H30B	−0.9268	0.1135	0.0164	0.124*
H30C	−0.6984	0.1450	0.0137	0.124*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.149 (5)	0.215 (6)	0.220 (6)	−0.017 (4)	−0.041 (4)	0.134 (5)
O2	0.095 (3)	0.113 (3)	0.155 (3)	−0.019 (2)	0.000 (3)	0.029 (3)
O3	0.0799 (17)	0.0553 (13)	0.0783 (16)	−0.0061 (13)	−0.0114 (15)	−0.0095 (12)
O4	0.093 (2)	0.106 (2)	0.091 (2)	−0.027 (2)	−0.0279 (19)	−0.0018 (19)
C1	0.062 (2)	0.0543 (16)	0.0494 (16)	−0.0038 (16)	0.0041 (16)	0.0012 (14)
C2	0.076 (2)	0.0571 (18)	0.0535 (18)	−0.0039 (18)	0.0032 (19)	−0.0014 (14)
C3	0.0559 (19)	0.0509 (16)	0.0638 (19)	−0.0009 (15)	−0.0101 (16)	−0.0013 (14)
C4	0.0474 (16)	0.0529 (16)	0.0607 (18)	−0.0008 (14)	−0.0073 (15)	0.0071 (14)
C5	0.0379 (14)	0.0571 (16)	0.0500 (15)	−0.0011 (13)	−0.0065 (13)	0.0076 (13)
C6	0.072 (2)	0.0662 (19)	0.0510 (17)	−0.0020 (18)	−0.0046 (16)	0.0121 (16)
C7	0.071 (2)	0.074 (2)	0.0455 (16)	−0.0075 (19)	0.0033 (16)	0.0056 (15)
C8	0.0385 (14)	0.0610 (17)	0.0463 (15)	−0.0051 (14)	0.0001 (12)	−0.0002 (13)
C9	0.0333 (13)	0.0548 (15)	0.0486 (15)	−0.0065 (13)	0.0001 (12)	0.0009 (13)
C10	0.0366 (14)	0.0555 (16)	0.0488 (15)	−0.0022 (13)	0.0003 (12)	−0.0005 (13)
C11	0.0495 (18)	0.0574 (17)	0.0561 (17)	−0.0068 (15)	0.0161 (15)	−0.0035 (14)
C12	0.0484 (17)	0.0561 (17)	0.0606 (18)	−0.0035 (14)	0.0130 (16)	−0.0057 (15)
C13	0.0350 (14)	0.0612 (17)	0.0484 (15)	−0.0030 (13)	0.0011 (12)	−0.0085 (14)
C14	0.0387 (15)	0.0682 (19)	0.0443 (15)	−0.0035 (15)	0.0029 (12)	−0.0061 (14)
C15	0.062 (2)	0.086 (3)	0.0553 (19)	−0.005 (2)	0.0145 (17)	−0.0062 (18)
C16	0.0521 (19)	0.089 (3)	0.063 (2)	0.001 (2)	0.0113 (17)	−0.0181 (19)
C17	0.0429 (16)	0.0678 (19)	0.0576 (18)	0.0017 (16)	0.0029 (15)	−0.0134 (15)
C18	0.0437 (16)	0.076 (2)	0.0641 (19)	−0.0002 (17)	−0.0054 (16)	−0.0100 (17)
C19	0.063 (2)	0.082 (2)	0.063 (2)	0.002 (2)	−0.0177 (18)	−0.0115 (19)
C20	0.0415 (17)	0.067 (2)	0.089 (3)	−0.0021 (16)	−0.0024 (17)	−0.0080 (19)
C21	0.066 (2)	0.063 (2)	0.081 (2)	−0.0124 (19)	−0.004 (2)	0.0111 (19)
C22	0.068 (2)	0.062 (2)	0.085 (3)	0.0105 (19)	−0.016 (2)	0.0042 (19)
C23	0.057 (2)	0.077 (2)	0.073 (2)	0.0133 (19)	0.0008 (19)	−0.0171 (19)
C24	0.090 (3)	0.091 (3)	0.095 (3)	0.027 (3)	0.016 (3)	−0.019 (3)
C25	0.081 (3)	0.068 (2)	0.079 (2)	0.018 (2)	−0.011 (2)	−0.012 (2)
C26	0.091 (3)	0.079 (3)	0.090 (3)	−0.003 (3)	−0.007 (3)	−0.011 (2)
C27	0.096 (4)	0.064 (2)	0.102 (3)	0.015 (2)	−0.002 (3)	0.011 (2)
C28	0.127 (5)	0.093 (4)	0.218 (8)	0.004 (4)	0.056 (6)	0.035 (5)
C29	0.105 (3)	0.062 (2)	0.061 (2)	−0.021 (2)	−0.023 (2)	0.0097 (17)
C30	0.163 (5)	0.060 (2)	0.088 (3)	−0.016 (3)	−0.036 (3)	−0.004 (2)

Geometric parameters (Å, º)

O1—C27	1.179 (7)	C15—C16	1.537 (6)
O2—C27	1.302 (7)	C15—H15A	0.9600
O2—C28	1.464 (7)	C15—H15B	0.9599
O3—C29	1.335 (5)	C16—C17	1.554 (5)
O3—C3	1.447 (4)	C16—H16A	0.9600
O4—C29	1.196 (6)	C16—H16B	0.9600
C1—C2	1.533 (4)	C17—C23	1.527 (5)
C1—C10	1.548 (4)	C17—H17	0.9600
C1—H1A	0.9600	C18—H18A	0.9600
C1—H1B	0.9602	C18—H18B	0.9600
C2—C3	1.500 (5)	C18—H18C	0.9600
C2—H2A	0.9599	C19—H19A	0.9600
C2—H2B	0.9601	C19—H19B	0.9600
C3—C4	1.545 (5)	C19—H19C	0.9600
C3—H3	0.9599	C20—H20A	0.9600
C4—C22	1.526 (5)	C20—H20B	0.9600
C4—C21	1.539 (5)	C20—H20C	0.9600
C4—C5	1.553 (4)	C21—H21A	0.9600
C5—C6	1.529 (4)	C21—H21B	0.9600
C5—C10	1.547 (4)	C21—H21C	0.9600
C5—H5	0.9600	C22—H22A	0.9600
C6—C7	1.510 (5)	C22—H22B	0.9600
C6—H6A	0.9600	C22—H22C	0.9600
C6—H6B	0.9599	C23—C25	1.524 (6)
C7—C8	1.495 (4)	C23—C24	1.528 (5)
C7—H7A	0.9602	C23—H23	0.9599
C7—H7B	0.9600	C24—H24A	0.9600
C8—C9	1.342 (4)	C24—H24B	0.9600
C8—C14	1.515 (4)	C24—H24C	0.9600
C9—C11	1.516 (4)	C25—C26	1.508 (6)
C9—C10	1.538 (4)	C25—H25A	0.9600
C10—C20	1.552 (5)	C25—H25B	0.9600
C11—C12	1.535 (4)	C26—C27	1.495 (7)
C11—H11A	0.9600	C26—H26A	0.9599
C11—H11B	0.9600	C26—H26B	0.9599
C12—C13	1.525 (4)	C28—H28A	0.9600
C12—H12A	0.9601	C28—H28B	0.9600
C12—H12B	0.9600	C28—H28C	0.9600
C13—C18	1.550 (4)	C29—C30	1.492 (7)
C13—C14	1.550 (5)	C30—H30A	0.9600
C13—C17	1.553 (4)	C30—H30B	0.9600
C14—C15	1.535 (4)	C30—H30C	0.9600
C14—C19	1.548 (5)
C27—O2—C28	116.8 (5)	H15A—C15—H15B	109.5
C29—O3—C3	119.4 (3)	C15—C16—C17	108.2 (3)
C2—C1—C10	112.6 (3)	C15—C16—H16A	109.1
C2—C1—H1A	109.5	C17—C16—H16A	110.7
C10—C1—H1A	106.9	C15—C16—H16B	110.1
C2—C1—H1B	110.0	C17—C16—H16B	109.3
C10—C1—H1B	108.3	H16A—C16—H16B	109.5
H1A—C1—H1B	109.5	C23—C17—C13	120.0 (3)
C3—C2—C1	110.9 (3)	C23—C17—C16	112.1 (3)
C3—C2—H2A	108.7	C13—C17—C16	101.8 (3)
C1—C2—H2A	109.5	C23—C17—H17	104.0
C3—C2—H2B	109.3	C13—C17—H17	110.3
C1—C2—H2B	108.9	C16—C17—H17	108.4
H2A—C2—H2B	109.5	C13—C18—H18A	109.5
O3—C3—C2	107.0 (3)	C13—C18—H18B	109.5
O3—C3—C4	110.3 (3)	H18A—C18—H18B	109.5
C2—C3—C4	114.2 (3)	C13—C18—H18C	109.5
O3—C3—H3	109.9	H18A—C18—H18C	109.5
C2—C3—H3	109.3	H18B—C18—H18C	109.5
C4—C3—H3	106.2	C14—C19—H19A	109.5
C22—C4—C21	107.3 (3)	C14—C19—H19B	109.5
C22—C4—C3	111.2 (3)	H19A—C19—H19B	109.5
C21—C4—C3	107.7 (3)	C14—C19—H19C	109.5
C22—C4—C5	114.9 (3)	H19A—C19—H19C	109.5
C21—C4—C5	109.5 (3)	H19B—C19—H19C	109.5
C3—C4—C5	106.0 (2)	C10—C20—H20A	109.5
C6—C5—C10	109.8 (3)	C10—C20—H20B	109.5
C6—C5—C4	114.4 (3)	H20A—C20—H20B	109.5
C10—C5—C4	118.1 (3)	C10—C20—H20C	109.5
C6—C5—H5	109.9	H20A—C20—H20C	109.5
C10—C5—H5	102.9	H20B—C20—H20C	109.5
C4—C5—H5	100.4	C4—C21—H21A	109.5
C7—C6—C5	109.0 (3)	C4—C21—H21B	109.5
C7—C6—H6A	109.6	H21A—C21—H21B	109.5
C5—C6—H6A	109.9	C4—C21—H21C	109.5
C7—C6—H6B	109.8	H21A—C21—H21C	109.5
C5—C6—H6B	109.1	H21B—C21—H21C	109.5
H6A—C6—H6B	109.5	C4—C22—H22A	109.5
C8—C7—C6	114.3 (3)	C4—C22—H22B	109.5
C8—C7—H7A	108.1	H22A—C22—H22B	109.5
C6—C7—H7A	109.9	C4—C22—H22C	109.5
C8—C7—H7B	105.7	H22A—C22—H22C	109.5
C6—C7—H7B	109.3	H22B—C22—H22C	109.5
H7A—C7—H7B	109.5	C25—C23—C17	116.3 (3)
C9—C8—C7	123.4 (3)	C25—C23—C24	109.9 (3)
C9—C8—C14	120.2 (3)	C17—C23—C24	111.8 (3)
C7—C8—C14	116.3 (3)	C25—C23—H23	105.7
C8—C9—C11	121.9 (3)	C17—C23—H23	104.3
C8—C9—C10	122.1 (3)	C24—C23—H23	108.3
C11—C9—C10	115.9 (2)	C23—C24—H24A	109.5
C9—C10—C5	108.7 (2)	C23—C24—H24B	109.5
C9—C10—C1	110.4 (3)	H24A—C24—H24B	109.5
C5—C10—C1	107.2 (2)	C23—C24—H24C	109.5
C9—C10—C20	107.4 (3)	H24A—C24—H24C	109.5
C5—C10—C20	114.7 (3)	H24B—C24—H24C	109.5
C1—C10—C20	108.3 (3)	C26—C25—C23	115.1 (4)
C9—C11—C12	117.1 (2)	C26—C25—H25A	106.0
C9—C11—H11A	109.4	C23—C25—H25A	108.7
C12—C11—H11A	105.2	C26—C25—H25B	107.7
C9—C11—H11B	110.1	C23—C25—H25B	109.7
C12—C11—H11B	105.2	H25A—C25—H25B	109.5
H11A—C11—H11B	109.5	C27—C26—C25	113.9 (4)
C13—C12—C11	110.6 (3)	C27—C26—H26A	107.8
C13—C12—H12A	108.9	C25—C26—H26A	108.3
C11—C12—H12A	109.1	C27—C26—H26B	107.8
C13—C12—H12B	109.3	C25—C26—H26B	109.5
C11—C12—H12B	109.5	H26A—C26—H26B	109.5
H12A—C12—H12B	109.5	O1—C27—O2	121.5 (6)
C12—C13—C18	108.3 (2)	O1—C27—C26	124.6 (6)
C12—C13—C14	107.6 (3)	O2—C27—C26	113.7 (5)
C18—C13—C14	111.0 (3)	O2—C28—H28A	109.5
C12—C13—C17	118.9 (3)	O2—C28—H28B	109.5
C18—C13—C17	108.8 (3)	H28A—C28—H28B	109.5
C14—C13—C17	102.1 (2)	O2—C28—H28C	109.5
C8—C14—C15	118.2 (3)	H28A—C28—H28C	109.5
C8—C14—C19	105.7 (3)	H28B—C28—H28C	109.5
C15—C14—C19	106.9 (3)	O4—C29—O3	123.8 (4)
C8—C14—C13	111.4 (2)	O4—C29—C30	125.6 (5)
C15—C14—C13	101.8 (3)	O3—C29—C30	110.5 (5)
C19—C14—C13	113.1 (3)	C29—C30—H30A	109.5
C14—C15—C16	104.1 (3)	C29—C30—H30B	109.5
C14—C15—H15A	111.0	H30A—C30—H30B	109.5
C16—C15—H15A	112.3	C29—C30—H30C	109.5
C14—C15—H15B	108.5	H30A—C30—H30C	109.5
C16—C15—H15B	111.4	H30B—C30—H30C	109.5