Incaniline (isoargentatin A) from Parthenium argentatum

The title compound, (20S,24R)-incanilin, C₃₀H₄₈O₄, contains three six-membered rings and two five-membered rings. The six-membered ring B adopts a distorted envelope conformation and five-membered ring D adopts a twist conformation. In the crystal structure, the mol­ecules exist as O—H...O hydrogen-bonded dimers.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.049
• wR factor = 0.117
• Data-to-parameter ratio = 8.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C23
PLAT417_ALERT_2_B Short Inter D-H..H-D       H2     ..  H4      ..       2.02 Ang.

Alert level C
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.57 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C10    -   C19     ..       5.46 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C25
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           25.00
           From the CIF: _reflns_number_total               2652
           Count of symmetry unique reflns         2653
           Completeness (_total/calc)             99.96%
           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
   2 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

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

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PARST95 (Nardelli, 1995).

(20S,24R)-Incanilin

Crystal data

C30H48O4	F(000) = 2080
Mr = 472.68	Dx = 1.155 Mg m^−3
Orthorhombic, C2221	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2c 2	Cell parameters from 8001 reflections
a = 13.9158 (7) Å	θ = 2.2–31.0°
b = 14.8078 (8) Å	µ = 0.07 mm^−1
c = 26.3807 (14) Å	T = 291 K
V = 5436.1 (5) Å^3	Prism, colourless
Z = 8	0.40 × 0.30 × 0.30 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2096 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.047
Graphite monochromator	θmax = 25.0°, θmin = 2.0°
φ and ω scans	h = −16→16
22368 measured reflections	k = −17→17
2652 independent reflections	l = −31→31

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.117	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0707P)^2] where P = (Fo^2 + 2Fc^2)/3
2652 reflections	(Δ/σ)max = 0.006
309 parameters	Δρmax = 0.17 e Å^−3
6 restraints	Δρmin = −0.16 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	0.1622 (2)	1.1890 (2)	0.80297 (11)	0.1013 (10)
O2	0.0448 (2)	0.62575 (16)	0.54585 (11)	0.0829 (8)
H2	0.0581	0.5771	0.5589	0.124*
O3	−0.01747 (16)	0.73486 (17)	0.46729 (9)	0.0700 (7)
O4	0.0341 (4)	0.5554 (2)	0.44942 (11)	0.1307 (15)
H4	0.0891	0.5514	0.4604	0.196*
C1	0.0801 (3)	1.1257 (2)	0.68383 (13)	0.0612 (9)
H1A	0.0579	1.1548	0.6531	0.073*
H1B	0.0241	1.1066	0.7029	0.073*
C2	0.1370 (3)	1.1936 (2)	0.71529 (15)	0.0739 (10)
H2A	0.1893	1.2172	0.6949	0.089*
H2B	0.0954	1.2437	0.7242	0.089*
C3	0.1770 (3)	1.1539 (2)	0.76229 (15)	0.0692 (10)
C4	0.2342 (3)	1.0673 (2)	0.75658 (14)	0.0659 (10)
C5	0.1795 (2)	1.0024 (2)	0.71974 (12)	0.0549 (8)
H5	0.1221	0.9842	0.7387	0.066*
C6	0.2316 (3)	0.9148 (2)	0.70922 (14)	0.0681 (10)
H6A	0.2604	0.8925	0.7403	0.082*
H6B	0.2827	0.9253	0.6849	0.082*
C7	0.1620 (3)	0.8449 (2)	0.68838 (13)	0.0622 (9)
H7A	0.1984	0.7986	0.6708	0.075*
H7B	0.1292	0.8162	0.7166	0.075*
C8	0.0884 (2)	0.8822 (2)	0.65290 (11)	0.0474 (7)
C9	0.0767 (2)	0.97027 (19)	0.64417 (11)	0.0456 (7)
C10	0.1397 (2)	1.04256 (19)	0.66974 (11)	0.0471 (7)
C11	0.0036 (3)	1.0041 (2)	0.60617 (13)	0.0560 (8)
H11A	0.0374	1.0408	0.5815	0.067*
H11B	−0.0405	1.0437	0.6240	0.067*
C12	−0.0563 (2)	0.9344 (2)	0.57703 (13)	0.0572 (8)
H12A	−0.1178	0.9269	0.5938	0.069*
H12B	−0.0685	0.9568	0.5431	0.069*
C13	−0.0064 (2)	0.8434 (2)	0.57354 (12)	0.0481 (7)
C14	0.0191 (2)	0.81489 (19)	0.62927 (12)	0.0497 (8)
C15	0.0532 (3)	0.7177 (2)	0.62141 (13)	0.0633 (9)
H15A	0.1198	0.7166	0.6106	0.076*
H15B	0.0473	0.6834	0.6526	0.076*
C16	−0.0117 (3)	0.6782 (2)	0.58043 (13)	0.0629 (9)
H16	−0.0592	0.6386	0.5965	0.076*
C17	−0.0654 (2)	0.7602 (2)	0.55577 (12)	0.0552 (8)
H17	−0.1255	0.7645	0.5750	0.066*
C18	0.0837 (2)	0.8536 (2)	0.54100 (12)	0.0547 (8)
H18A	0.0657	0.8710	0.5073	0.082*
H18B	0.1175	0.7971	0.5399	0.082*
H18C	0.1245	0.8991	0.5554	0.082*
C19	0.2172 (3)	1.0698 (2)	0.63072 (13)	0.0656 (9)
H19A	0.1867	1.0939	0.6010	0.098*
H19B	0.2544	1.0176	0.6216	0.098*
H19C	0.2586	1.1147	0.6453	0.098*
C20	−0.0985 (2)	0.7498 (3)	0.50019 (14)	0.0648 (9)
C21	−0.1530 (3)	0.8322 (3)	0.48138 (15)	0.0826 (12)
H21A	−0.1123	0.8844	0.4834	0.124*
H21B	−0.2090	0.8414	0.5020	0.124*
H21C	−0.1722	0.8229	0.4468	0.124*
C22	−0.1589 (3)	0.6643 (3)	0.49290 (15)	0.0867 (13)
H22A	−0.2259	0.6753	0.5009	0.104*
H22B	−0.1353	0.6153	0.5139	0.104*
C23	−0.1457 (3)	0.6431 (4)	0.43637 (18)	0.1170 (19)
H23A	−0.1966	0.6700	0.4163	0.140*
H23B	−0.1450	0.5785	0.4305	0.140*
C24	−0.0476 (3)	0.6855 (3)	0.42325 (15)	0.0756 (11)
H24	−0.0560	0.7278	0.3950	0.091*
C25	0.0315 (3)	0.6188 (3)	0.40991 (14)	0.0763 (11)
C26	0.0071 (4)	0.5688 (3)	0.36051 (15)	0.0978 (14)
H26A	0.0576	0.5271	0.3525	0.147*
H26B	0.0005	0.6117	0.3334	0.147*
H26C	−0.0522	0.5365	0.3647	0.147*
C27	0.1275 (3)	0.6654 (3)	0.40570 (16)	0.0827 (12)
H27A	0.1415	0.6962	0.4369	0.124*
H27B	0.1256	0.7084	0.3785	0.124*
H27C	0.1766	0.6215	0.3991	0.124*
C28	−0.0683 (3)	0.8116 (3)	0.66522 (13)	0.0703 (10)
H28A	−0.0475	0.7939	0.6985	0.105*
H28B	−0.1142	0.7687	0.6527	0.105*
H28C	−0.0975	0.8703	0.6669	0.105*
C29	0.2413 (4)	1.0234 (3)	0.80873 (15)	0.0989 (15)
H29A	0.2749	1.0631	0.8314	0.148*
H29B	0.2755	0.9673	0.8060	0.148*
H29C	0.1779	1.0122	0.8216	0.148*
C30	0.3364 (3)	1.0917 (3)	0.73858 (16)	0.0834 (12)
H30A	0.3329	1.1213	0.7063	0.125*
H30B	0.3740	1.0376	0.7355	0.125*
H30C	0.3660	1.1313	0.7628	0.125*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.110 (2)	0.109 (2)	0.085 (2)	−0.0281 (19)	0.0124 (18)	−0.0389 (19)
O2	0.111 (2)	0.0494 (14)	0.0884 (18)	0.0020 (16)	0.0052 (17)	−0.0107 (14)
O3	0.0586 (14)	0.0807 (16)	0.0706 (14)	−0.0268 (13)	0.0120 (12)	−0.0273 (13)
O4	0.261 (5)	0.0552 (15)	0.0758 (19)	−0.016 (2)	0.003 (3)	−0.0017 (15)
C1	0.066 (2)	0.0462 (18)	0.072 (2)	−0.0023 (17)	0.0012 (19)	−0.0016 (17)
C2	0.087 (3)	0.0494 (19)	0.085 (3)	−0.003 (2)	−0.002 (2)	−0.013 (2)
C3	0.070 (2)	0.071 (2)	0.067 (2)	−0.030 (2)	0.004 (2)	−0.016 (2)
C4	0.077 (2)	0.060 (2)	0.061 (2)	−0.021 (2)	−0.0104 (19)	0.0007 (18)
C5	0.0578 (19)	0.0500 (17)	0.0570 (18)	−0.0098 (17)	−0.0066 (16)	0.0047 (15)
C6	0.073 (2)	0.056 (2)	0.075 (2)	0.0031 (19)	−0.024 (2)	0.0060 (18)
C7	0.084 (3)	0.0427 (17)	0.060 (2)	0.0046 (18)	−0.0165 (19)	0.0007 (15)
C8	0.0568 (18)	0.0403 (16)	0.0450 (16)	0.0016 (15)	0.0007 (15)	0.0068 (14)
C9	0.0474 (17)	0.0433 (17)	0.0461 (17)	−0.0007 (14)	−0.0001 (14)	0.0037 (13)
C10	0.0520 (17)	0.0373 (15)	0.0520 (17)	−0.0027 (15)	0.0023 (15)	0.0028 (14)
C11	0.0614 (19)	0.0445 (15)	0.062 (2)	0.0006 (17)	−0.0091 (17)	0.0049 (15)
C12	0.0548 (19)	0.054 (2)	0.063 (2)	−0.0005 (17)	−0.0066 (17)	0.0062 (17)
C13	0.0472 (17)	0.0482 (16)	0.0488 (17)	−0.0072 (15)	−0.0019 (15)	0.0029 (14)
C14	0.0603 (19)	0.0398 (15)	0.0490 (17)	−0.0063 (15)	0.0001 (16)	0.0057 (14)
C15	0.084 (2)	0.0408 (17)	0.066 (2)	−0.0037 (17)	−0.0036 (19)	0.0040 (16)
C16	0.077 (2)	0.0449 (18)	0.067 (2)	−0.0164 (18)	0.011 (2)	−0.0008 (16)
C17	0.0516 (18)	0.0535 (19)	0.060 (2)	−0.0151 (16)	0.0091 (15)	−0.0009 (16)
C18	0.0543 (18)	0.0575 (19)	0.0524 (18)	−0.0144 (16)	−0.0013 (16)	0.0027 (15)
C19	0.069 (2)	0.065 (2)	0.064 (2)	−0.0093 (19)	0.0018 (19)	0.0010 (19)
C20	0.0508 (18)	0.081 (2)	0.0624 (19)	−0.0196 (19)	0.0065 (17)	−0.0146 (19)
C21	0.071 (2)	0.111 (3)	0.066 (2)	−0.003 (3)	−0.014 (2)	−0.007 (2)
C22	0.072 (2)	0.111 (3)	0.077 (3)	−0.046 (3)	0.008 (2)	−0.023 (2)
C23	0.091 (3)	0.157 (5)	0.103 (3)	−0.063 (3)	0.024 (3)	−0.055 (3)
C24	0.074 (2)	0.086 (3)	0.067 (2)	−0.029 (2)	0.007 (2)	−0.020 (2)
C25	0.111 (3)	0.057 (2)	0.060 (2)	−0.012 (2)	0.001 (2)	−0.0090 (19)
C26	0.122 (4)	0.102 (3)	0.070 (3)	−0.018 (3)	0.007 (3)	−0.030 (2)
C27	0.078 (3)	0.082 (3)	0.089 (3)	0.007 (2)	−0.001 (2)	−0.013 (2)
C28	0.084 (3)	0.067 (2)	0.060 (2)	−0.019 (2)	0.0113 (19)	0.0015 (18)
C29	0.127 (4)	0.100 (3)	0.069 (2)	−0.041 (3)	−0.032 (3)	0.005 (2)
C30	0.068 (2)	0.085 (3)	0.098 (3)	−0.020 (2)	−0.015 (2)	−0.004 (2)

Geometric parameters (Å, º)

O1—C3	1.210 (4)	C15—C16	1.525 (5)
O2—C16	1.433 (4)	C15—H15A	0.97
O2—H2	0.82	C15—H15B	0.97
O3—C24	1.435 (4)	C16—C17	1.567 (5)
O3—C20	1.439 (4)	C16—H16	0.98
O4—C25	1.404 (5)	C17—C20	1.544 (5)
O4—H4	0.82	C17—H17	0.98
C1—C2	1.525 (5)	C18—H18A	0.96
C1—C10	1.530 (4)	C18—H18B	0.96
C1—H1A	0.97	C18—H18C	0.96
C1—H1B	0.97	C19—H19A	0.96
C2—C3	1.481 (5)	C19—H19B	0.96
C2—H2A	0.97	C19—H19C	0.96
C2—H2B	0.97	C20—C21	1.521 (6)
C3—C4	1.517 (5)	C20—C22	1.532 (5)
C4—C29	1.524 (5)	C21—H21A	0.96
C4—C30	1.543 (5)	C21—H21B	0.96
C4—C5	1.564 (5)	C21—H21C	0.96
C5—C6	1.512 (5)	C22—C23	1.535 (6)
C5—C10	1.549 (4)	C22—H22A	0.97
C5—H5	0.98	C22—H22B	0.97
C6—C7	1.521 (5)	C23—C24	1.541 (6)
C6—H6A	0.97	C23—H23A	0.97
C6—H6B	0.97	C23—H23B	0.97
C7—C8	1.493 (4)	C24—C25	1.520 (6)
C7—H7A	0.97	C24—H24	0.98
C7—H7B	0.97	C25—C27	1.507 (6)
C8—C9	1.335 (4)	C25—C26	1.537 (5)
C8—C14	1.520 (4)	C26—H26A	0.96
C9—C11	1.513 (4)	C26—H26B	0.96
C9—C10	1.540 (4)	C26—H26C	0.96
C10—C19	1.544 (5)	C27—H27A	0.96
C11—C12	1.533 (5)	C27—H27B	0.96
C11—H11A	0.97	C27—H27C	0.96
C11—H11B	0.97	C28—H28A	0.96
C12—C13	1.519 (4)	C28—H28B	0.96
C12—H12A	0.97	C28—H28C	0.96
C12—H12B	0.97	C29—H29A	0.96
C13—C18	1.527 (5)	C29—H29B	0.96
C13—C17	1.553 (4)	C29—H29C	0.96
C13—C14	1.570 (4)	C30—H30A	0.96
C14—C15	1.529 (4)	C30—H30B	0.96
C14—C28	1.543 (5)	C30—H30C	0.96
C16—O2—H2	109.5	O2—C16—H16	108.7
C24—O3—C20	109.7 (2)	C15—C16—H16	108.7
C25—O4—H4	109.5	C17—C16—H16	108.7
C2—C1—C10	112.4 (3)	C20—C17—C13	121.5 (3)
C2—C1—H1A	109.1	C20—C17—C16	117.3 (3)
C10—C1—H1A	109.1	C13—C17—C16	103.7 (2)
C2—C1—H1B	109.1	C20—C17—H17	104.1
C10—C1—H1B	109.1	C13—C17—H17	104.1
H1A—C1—H1B	107.9	C16—C17—H17	104.1
C3—C2—C1	112.9 (3)	C13—C18—H18A	109.5
C3—C2—H2A	109.0	C13—C18—H18B	109.5
C1—C2—H2A	109.0	H18A—C18—H18B	109.5
C3—C2—H2B	109.0	C13—C18—H18C	109.5
C1—C2—H2B	109.0	H18A—C18—H18C	109.5
H2A—C2—H2B	107.8	H18B—C18—H18C	109.5
O1—C3—C2	120.6 (4)	C10—C19—H19A	109.5
O1—C3—C4	122.7 (4)	C10—C19—H19B	109.5
C2—C3—C4	116.7 (3)	H19A—C19—H19B	109.5
C3—C4—C29	107.7 (3)	C10—C19—H19C	109.5
C3—C4—C30	108.4 (3)	H19A—C19—H19C	109.5
C29—C4—C30	108.5 (3)	H19B—C19—H19C	109.5
C3—C4—C5	109.0 (3)	O3—C20—C21	108.5 (3)
C29—C4—C5	109.3 (3)	O3—C20—C22	103.1 (3)
C30—C4—C5	113.7 (3)	C21—C20—C22	110.4 (3)
C6—C5—C10	110.1 (3)	O3—C20—C17	110.8 (3)
C6—C5—C4	114.0 (3)	C21—C20—C17	112.2 (3)
C10—C5—C4	117.9 (3)	C22—C20—C17	111.4 (3)
C6—C5—H5	104.4	C20—C21—H21A	109.5
C10—C5—H5	104.4	C20—C21—H21B	109.5
C4—C5—H5	104.4	H21A—C21—H21B	109.5
C5—C6—C7	110.1 (3)	C20—C21—H21C	109.5
C5—C6—H6A	109.6	H21A—C21—H21C	109.5
C7—C6—H6A	109.6	H21B—C21—H21C	109.5
C5—C6—H6B	109.6	C20—C22—C23	103.0 (3)
C7—C6—H6B	109.6	C20—C22—H22A	111.2
H6A—C6—H6B	108.1	C23—C22—H22A	111.2
C8—C7—C6	114.3 (3)	C20—C22—H22B	111.2
C8—C7—H7A	108.7	C23—C22—H22B	111.2
C6—C7—H7A	108.7	H22A—C22—H22B	109.1
C8—C7—H7B	108.7	C22—C23—C24	103.9 (3)
C6—C7—H7B	108.7	C22—C23—H23A	111.0
H7A—C7—H7B	107.6	C24—C23—H23A	111.0
C9—C8—C7	123.6 (3)	C22—C23—H23B	111.0
C9—C8—C14	119.5 (3)	C24—C23—H23B	111.0
C7—C8—C14	116.7 (2)	H23A—C23—H23B	109.0
C8—C9—C11	121.4 (3)	O3—C24—C25	107.8 (3)
C8—C9—C10	122.3 (3)	O3—C24—C23	106.5 (3)
C11—C9—C10	116.3 (2)	C25—C24—C23	115.4 (4)
C1—C10—C9	110.9 (2)	O3—C24—H24	109.0
C1—C10—C19	109.3 (3)	C25—C24—H24	109.0
C9—C10—C19	106.7 (2)	C23—C24—H24	109.0
C1—C10—C5	107.2 (3)	O4—C25—C27	109.8 (4)
C9—C10—C5	108.1 (2)	O4—C25—C24	106.3 (3)
C19—C10—C5	114.7 (3)	C27—C25—C24	111.2 (3)
C9—C11—C12	118.3 (3)	O4—C25—C26	108.2 (3)
C9—C11—H11A	107.7	C27—C25—C26	110.8 (3)
C12—C11—H11A	107.7	C24—C25—C26	110.4 (4)
C9—C11—H11B	107.7	C25—C26—H26A	109.5
C12—C11—H11B	107.7	C25—C26—H26B	109.5
H11A—C11—H11B	107.1	H26A—C26—H26B	109.5
C13—C12—C11	112.3 (3)	C25—C26—H26C	109.5
C13—C12—H12A	109.1	H26A—C26—H26C	109.5
C11—C12—H12A	109.1	H26B—C26—H26C	109.5
C13—C12—H12B	109.1	C25—C27—H27A	109.5
C11—C12—H12B	109.1	C25—C27—H27B	109.5
H12A—C12—H12B	107.9	H27A—C27—H27B	109.5
C12—C13—C18	108.7 (3)	C25—C27—H27C	109.5
C12—C13—C17	118.8 (3)	H27A—C27—H27C	109.5
C18—C13—C17	110.0 (3)	H27B—C27—H27C	109.5
C12—C13—C14	106.6 (3)	C14—C28—H28A	109.5
C18—C13—C14	111.5 (2)	C14—C28—H28B	109.5
C17—C13—C14	100.9 (2)	H28A—C28—H28B	109.5
C8—C14—C15	118.4 (3)	C14—C28—H28C	109.5
C8—C14—C28	105.6 (3)	H28A—C28—H28C	109.5
C15—C14—C28	107.3 (3)	H28B—C28—H28C	109.5
C8—C14—C13	110.6 (2)	C4—C29—H29A	109.5
C15—C14—C13	101.3 (2)	C4—C29—H29B	109.5
C28—C14—C13	113.9 (3)	H29A—C29—H29B	109.5
C16—C15—C14	105.9 (3)	C4—C29—H29C	109.5
C16—C15—H15A	110.6	H29A—C29—H29C	109.5
C14—C15—H15A	110.6	H29B—C29—H29C	109.5
C16—C15—H15B	110.6	C4—C30—H30A	109.5
C14—C15—H15B	110.6	C4—C30—H30B	109.5
H15A—C15—H15B	108.7	H30A—C30—H30B	109.5
O2—C16—C15	109.6 (3)	C4—C30—H30C	109.5
O2—C16—C17	114.6 (3)	H30A—C30—H30C	109.5
C15—C16—C17	106.2 (2)	H30B—C30—H30C	109.5
C10—C1—C2—C3	−56.7 (4)	C9—C8—C14—C13	39.9 (4)
C1—C2—C3—O1	−127.1 (4)	C7—C8—C14—C13	−144.8 (3)
C1—C2—C3—C4	51.3 (5)	C12—C13—C14—C8	−62.3 (3)
O1—C3—C4—C29	15.7 (5)	C18—C13—C14—C8	56.2 (3)
C2—C3—C4—C29	−162.6 (3)	C17—C13—C14—C8	173.0 (2)
O1—C3—C4—C30	−101.5 (4)	C12—C13—C14—C15	171.3 (3)
C2—C3—C4—C30	80.1 (4)	C18—C13—C14—C15	−70.2 (3)
O1—C3—C4—C5	134.3 (4)	C17—C13—C14—C15	46.6 (3)
C2—C3—C4—C5	−44.1 (4)	C12—C13—C14—C28	56.4 (3)
C3—C4—C5—C6	177.6 (3)	C18—C13—C14—C28	174.9 (3)
C29—C4—C5—C6	−64.9 (4)	C17—C13—C14—C28	−68.3 (3)
C30—C4—C5—C6	56.5 (4)	C8—C14—C15—C16	−158.5 (3)
C3—C4—C5—C10	46.1 (4)	C28—C14—C15—C16	82.2 (3)
C29—C4—C5—C10	163.6 (3)	C13—C14—C15—C16	−37.5 (3)
C30—C4—C5—C10	−74.9 (4)	C14—C15—C16—O2	138.1 (3)
C10—C5—C6—C7	−63.5 (4)	C14—C15—C16—C17	13.7 (3)
C4—C5—C6—C7	161.3 (3)	C12—C13—C17—C20	71.1 (4)
C5—C6—C7—C8	38.1 (4)	C18—C13—C17—C20	−55.1 (4)
C6—C7—C8—C9	−7.2 (5)	C14—C13—C17—C20	−173.0 (3)
C6—C7—C8—C14	177.7 (3)	C12—C13—C17—C16	−154.1 (3)
C7—C8—C9—C11	177.5 (3)	C18—C13—C17—C16	79.7 (3)
C14—C8—C9—C11	−7.6 (5)	C14—C13—C17—C16	−38.2 (3)
C7—C8—C9—C10	0.8 (5)	O2—C16—C17—C20	31.7 (4)
C14—C8—C9—C10	175.7 (3)	C15—C16—C17—C20	152.9 (3)
C2—C1—C10—C9	172.6 (3)	O2—C16—C17—C13	−105.3 (3)
C2—C1—C10—C19	−70.1 (4)	C15—C16—C17—C13	15.8 (3)
C2—C1—C10—C5	54.9 (4)	C24—O3—C20—C21	−83.0 (4)
C8—C9—C10—C1	−141.7 (3)	C24—O3—C20—C22	34.0 (4)
C11—C9—C10—C1	41.5 (4)	C24—O3—C20—C17	153.3 (3)
C8—C9—C10—C19	99.3 (3)	C13—C17—C20—O3	68.2 (4)
C11—C9—C10—C19	−77.5 (3)	C16—C17—C20—O3	−60.8 (4)
C8—C9—C10—C5	−24.5 (4)	C13—C17—C20—C21	−53.2 (4)
C11—C9—C10—C5	158.7 (3)	C16—C17—C20—C21	177.7 (3)
C6—C5—C10—C1	174.7 (3)	C13—C17—C20—C22	−177.6 (3)
C4—C5—C10—C1	−52.1 (4)	C16—C17—C20—C22	53.4 (4)
C6—C5—C10—C9	55.2 (3)	O3—C20—C22—C23	−36.6 (4)
C4—C5—C10—C9	−171.6 (3)	C21—C20—C22—C23	79.2 (4)
C6—C5—C10—C19	−63.7 (3)	C17—C20—C22—C23	−155.4 (4)
C4—C5—C10—C19	69.5 (4)	C20—C22—C23—C24	26.2 (5)
C8—C9—C11—C12	−0.9 (5)	C20—O3—C24—C25	−141.7 (3)
C10—C9—C11—C12	176.0 (3)	C20—O3—C24—C23	−17.2 (5)
C9—C11—C12—C13	−24.6 (4)	C22—C23—C24—O3	−6.7 (5)
C11—C12—C13—C18	−66.2 (3)	C22—C23—C24—C25	112.9 (4)
C11—C12—C13—C17	167.0 (3)	O3—C24—C25—O4	67.2 (4)
C11—C12—C13—C14	54.1 (3)	C23—C24—C25—O4	−51.7 (5)
C9—C8—C14—C15	156.1 (3)	O3—C24—C25—C27	−52.3 (4)
C7—C8—C14—C15	−28.6 (4)	C23—C24—C25—C27	−171.2 (4)
C9—C8—C14—C28	−83.7 (3)	O3—C24—C25—C26	−175.6 (3)
C7—C8—C14—C28	91.5 (3)	C23—C24—C25—C26	65.5 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O4^i	0.82	2.00	2.689 (4)	141

Symmetry code: (i) x, −y+1, −z+1.