3,7,17-Tri-O-acetyl-5-O-butanoyl-13,15-di­hydroxy­myrisinol

The structure of the tricyclic diterpenoid, C₃₀H₄₂O₁₁, is composed of a five-membered ring in a C4-envelope conformation, a seven-membered ring in a chair conformation and a six-membered ring that adopts a twisted half-chair conformation. The structure is stabilized by intramolecular and intermolecular hydrogen-bond interactions, with O...O separations of 2.815 (4) and 2.812 (4) Å.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.048
• wR factor = 0.139
• Data-to-parameter ratio = 8.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT410_ALERT_2_B Short Intra H...H Contact  H19B   ..  H21F     =       1.80 Ang.
PLAT412_ALERT_2_B Short Intra XH3 .. XHn     H11    ..  H30B     =       1.76 Ang.

Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.98
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.21 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.98 Ratio
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C23
PLAT301_ALERT_3_C Main Residue  Disorder .........................       5.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ......        C29
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C30 H42 O11

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               2943
           Count of symmetry unique reflns         2978
           Completeness (_total/calc)             98.82%
           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
   8 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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
   3 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: COLLECT (Hooft, 1998); cell refinement: HKL DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

3,7,17-O-triacetyl-5-O-butanoyl-13,15-dihydroxymyrisinol

Crystal data

C30H42O11	F(000) = 1240
Mr = 578.64	Dx = 1.285 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5134 reflections
a = 10.389 (3) Å	θ = 2.1–25.0°
b = 14.745 (4) Å	µ = 0.10 mm^−1
c = 19.531 (7) Å	T = 295 K
V = 2991.9 (16) Å^3	Block, colourless
Z = 4	0.10 × 0.09 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer	2416 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
Graphite monochromator	θmax = 25.0°, θmin = 2.1°
ω and φ scans	h = −12→12
5134 measured reflections	k = −17→17
2943 independent reflections	l = −23→22

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)] = 0.048	H-atom parameters constrained
wR(F^2) = 0.139	w = 1/[σ^2(Fo^2) + (0.0808P)^2 + 0.577P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
2943 reflections	Δρmax = 0.42 e Å^−3
369 parameters	Δρmin = −0.33 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.019 (4)

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.2155 (2)	0.45509 (17)	1.43342 (13)	0.0448 (6)
H1A	0.2077	0.4406	1.4737	0.067*
O2	0.1482 (2)	0.52681 (17)	1.30090 (12)	0.0442 (6)
O3	0.1217 (3)	0.5742 (2)	1.19268 (15)	0.0729 (9)
O4	0.4575 (3)	0.47766 (19)	1.26385 (13)	0.0531 (7)
O5	0.3132 (4)	0.3923 (2)	1.20824 (15)	0.0758 (10)
O6	0.6297 (2)	0.54490 (17)	1.39364 (13)	0.0456 (6)
O7	0.8416 (3)	0.5593 (3)	1.3928 (3)	0.1080 (16)
O8	0.4157 (2)	0.26784 (16)	1.32546 (13)	0.0456 (6)
O9	0.4764 (3)	0.2043 (2)	1.22632 (17)	0.0716 (9)
O10	0.3657 (3)	0.41340 (18)	1.54916 (12)	0.0465 (6)
H10A	0.3872	0.4236	1.5888	0.070*
O11	0.4262 (3)	0.61261 (17)	1.50587 (15)	0.0607 (8)
C1	0.2858 (3)	0.5375 (2)	1.42898 (18)	0.0388 (8)
C2	0.1939 (4)	0.6205 (3)	1.4293 (2)	0.0513 (10)
H2A	0.1060	0.6009	1.4371	0.062*
H2B	0.2179	0.6623	1.4654	0.062*
C3	0.2051 (4)	0.6665 (2)	1.3599 (2)	0.0478 (9)
H3	0.2742	0.7116	1.3632	0.057*
C4	0.2522 (3)	0.5908 (2)	1.3128 (2)	0.0429 (9)
H4	0.2893	0.6140	1.2701	0.051*
C5	0.3519 (3)	0.5435 (2)	1.35785 (17)	0.0365 (8)
H5	0.4252	0.5849	1.3625	0.044*
C6	0.4039 (3)	0.4543 (2)	1.33116 (16)	0.0384 (8)
H6	0.3321	0.4121	1.3248	0.046*
C7	0.5149 (3)	0.4043 (2)	1.37080 (18)	0.0376 (8)
C8	0.5386 (3)	0.3161 (2)	1.32846 (19)	0.0421 (8)
H8	0.5644	0.3328	1.2819	0.050*
C9	0.6375 (4)	0.2559 (2)	1.3580 (2)	0.0491 (9)
H9	0.6930	0.2240	1.3295	0.059*
C10	0.6470 (4)	0.2478 (2)	1.4245 (2)	0.0482 (9)
H10	0.7091	0.2082	1.4413	0.058*
C11	0.5650 (4)	0.2976 (2)	1.47587 (19)	0.0443 (9)
H11	0.6247	0.3271	1.5078	0.053*
C12	0.4765 (3)	0.3752 (2)	1.44602 (16)	0.0355 (7)
H12	0.3911	0.3476	1.4416	0.043*
C13	0.4603 (3)	0.4511 (2)	1.50307 (17)	0.0376 (8)
C14	0.3940 (4)	0.5406 (2)	1.48124 (17)	0.0401 (8)
C15	0.0840 (5)	0.7159 (3)	1.3362 (2)	0.0696 (13)
H15A	0.0994	0.7432	1.2924	0.084*
H15B	0.0620	0.7621	1.3688	0.084*
H15C	0.0143	0.6734	1.3326	0.084*
C16	0.0930 (4)	0.5246 (3)	1.2396 (2)	0.0544 (10)
C17	−0.0071 (6)	0.4530 (4)	1.2363 (3)	0.0793 (15)
H17A	−0.0461	0.4532	1.1917	0.095*
H17B	−0.0716	0.4646	1.2704	0.095*
H17C	0.0316	0.3950	1.2446	0.095*
C18	0.3985 (5)	0.4476 (3)	1.2078 (2)	0.0636 (12)
C19	0.4519 (8)	0.4924 (4)	1.1443 (2)	0.092 (2)
H19A	0.4026	0.5472	1.1360	0.111*
H19B	0.5397	0.5108	1.1540	0.111*
C20	0.4530 (13)	0.4404 (10)	1.0822 (8)	0.092 (3)*	0.50
H20A	0.4717	0.4802	1.0439	0.110*	0.50
H20B	0.3684	0.4144	1.0749	0.110*	0.50
C21	0.5559 (15)	0.3620 (11)	1.0844 (8)	0.114 (3)*	0.50
H21A	0.5834	0.3482	1.0386	0.171*	0.50
H21B	0.5183	0.3090	1.1048	0.171*	0.50
H21C	0.6286	0.3812	1.1111	0.171*	0.50
C20'	0.5056 (13)	0.4363 (11)	1.0922 (8)	0.092 (3)*	0.50
H20C	0.4398	0.3954	1.0752	0.110*	0.50
H20D	0.5337	0.4740	1.0543	0.110*	0.50
C21'	0.6070 (15)	0.3870 (11)	1.1157 (8)	0.114 (3)*	0.50
H21D	0.6545	0.3631	1.0776	0.171*	0.50
H21E	0.5760	0.3380	1.1435	0.171*	0.50
H21F	0.6621	0.4253	1.1426	0.171*	0.50
C22	0.6436 (4)	0.4544 (2)	1.3666 (2)	0.0440 (8)
H22A	0.7082	0.4217	1.3926	0.053*
H22B	0.6718	0.4573	1.3193	0.053*
C23	0.7392 (4)	0.5917 (3)	1.4039 (2)	0.0573 (11)
C24	0.7133 (5)	0.6857 (3)	1.4279 (3)	0.0718 (13)
H24A	0.7934	0.7169	1.4348	0.086*
H24B	0.6665	0.6837	1.4703	0.086*
H24C	0.6633	0.7173	1.3941	0.086*
C25	0.3973 (4)	0.2148 (3)	1.2704 (2)	0.0539 (10)
C26	0.2679 (5)	0.1721 (4)	1.2717 (3)	0.0838 (16)
H26A	0.2577	0.1343	1.2320	0.101*
H26B	0.2030	0.2184	1.2715	0.101*
H26C	0.2594	0.1359	1.3123	0.101*
C27	0.4921 (4)	0.2259 (3)	1.5174 (2)	0.0546 (11)
C28	0.4113 (5)	0.1675 (3)	1.4857 (3)	0.0688 (13)
H28A	0.3704	0.1222	1.5108	0.083*
H28B	0.3967	0.1725	1.4389	0.083*
C29	0.5186 (6)	0.2207 (4)	1.5918 (2)	0.0832 (16)
H29A	0.4672	0.1735	1.6118	0.100*
H29B	0.4975	0.2776	1.6129	0.100*
H29C	0.6081	0.2077	1.5989	0.100*
C30	0.5818 (4)	0.4738 (3)	1.54311 (19)	0.0461 (9)
H30A	0.6453	0.4984	1.5126	0.055*
H30B	0.6148	0.4198	1.5642	0.055*
H30C	0.5619	0.5177	1.5779	0.055*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0443 (12)	0.0476 (14)	0.0425 (14)	−0.0036 (12)	0.0010 (12)	0.0031 (12)
O2	0.0487 (13)	0.0476 (14)	0.0362 (13)	−0.0041 (12)	−0.0060 (11)	0.0050 (11)
O3	0.095 (2)	0.079 (2)	0.0446 (16)	−0.012 (2)	−0.0178 (17)	0.0165 (15)
O4	0.0705 (17)	0.0586 (16)	0.0303 (13)	0.0118 (15)	0.0101 (13)	0.0056 (12)
O5	0.111 (3)	0.073 (2)	0.0434 (18)	0.012 (2)	−0.0158 (18)	−0.0110 (16)
O6	0.0451 (13)	0.0400 (13)	0.0517 (15)	−0.0028 (12)	−0.0007 (12)	−0.0044 (12)
O7	0.0480 (18)	0.076 (2)	0.200 (5)	−0.0131 (19)	0.013 (2)	−0.031 (3)
O8	0.0532 (14)	0.0417 (13)	0.0418 (14)	−0.0012 (12)	0.0007 (12)	−0.0098 (11)
O9	0.086 (2)	0.070 (2)	0.0586 (19)	0.0132 (18)	0.0019 (18)	−0.0292 (16)
O10	0.0539 (14)	0.0530 (15)	0.0324 (13)	−0.0099 (13)	0.0064 (12)	0.0010 (12)
O11	0.080 (2)	0.0425 (15)	0.0597 (17)	0.0059 (15)	−0.0174 (16)	−0.0152 (13)
C1	0.0452 (17)	0.0354 (17)	0.0360 (18)	0.0031 (16)	0.0027 (15)	−0.0029 (15)
C2	0.056 (2)	0.047 (2)	0.050 (2)	0.0134 (19)	−0.0001 (19)	−0.0062 (18)
C3	0.054 (2)	0.0334 (18)	0.057 (2)	0.0039 (17)	−0.0028 (19)	0.0040 (17)
C4	0.0442 (19)	0.0373 (17)	0.047 (2)	−0.0031 (17)	−0.0007 (16)	0.0054 (16)
C5	0.0407 (17)	0.0360 (17)	0.0329 (18)	0.0013 (16)	−0.0011 (14)	0.0038 (15)
C6	0.0483 (18)	0.0396 (18)	0.0272 (17)	0.0031 (17)	0.0018 (15)	0.0013 (14)
C7	0.0420 (18)	0.0339 (16)	0.0368 (19)	0.0023 (16)	0.0022 (15)	−0.0026 (15)
C8	0.0455 (19)	0.0406 (18)	0.040 (2)	−0.0013 (17)	0.0060 (17)	−0.0080 (16)
C9	0.051 (2)	0.042 (2)	0.055 (2)	0.0087 (18)	0.0096 (19)	−0.0077 (19)
C10	0.0427 (19)	0.039 (2)	0.063 (3)	0.0070 (17)	−0.0007 (19)	−0.0019 (18)
C11	0.0471 (19)	0.0433 (19)	0.042 (2)	0.0069 (17)	−0.0054 (17)	−0.0002 (16)
C12	0.0388 (16)	0.0335 (16)	0.0341 (18)	0.0033 (15)	0.0007 (14)	−0.0037 (14)
C13	0.0438 (17)	0.0384 (17)	0.0306 (17)	−0.0021 (16)	0.0011 (14)	0.0007 (15)
C14	0.0510 (19)	0.0377 (18)	0.0316 (17)	0.0005 (17)	0.0020 (15)	−0.0037 (15)
C15	0.073 (3)	0.062 (3)	0.074 (3)	0.020 (3)	−0.004 (3)	0.010 (2)
C16	0.068 (2)	0.053 (2)	0.043 (2)	0.000 (2)	−0.010 (2)	0.0042 (19)
C17	0.087 (3)	0.087 (3)	0.064 (3)	−0.027 (3)	−0.022 (3)	0.001 (3)
C18	0.093 (3)	0.058 (3)	0.040 (2)	0.020 (3)	0.002 (2)	−0.005 (2)
C19	0.151 (6)	0.088 (4)	0.039 (2)	0.028 (4)	0.015 (3)	0.012 (2)
C22	0.0443 (18)	0.0415 (19)	0.046 (2)	0.0009 (17)	0.0097 (17)	−0.0015 (17)
C23	0.050 (2)	0.051 (2)	0.071 (3)	−0.015 (2)	−0.001 (2)	−0.002 (2)
C24	0.087 (3)	0.053 (2)	0.076 (3)	−0.014 (3)	−0.001 (3)	−0.011 (2)
C25	0.071 (3)	0.042 (2)	0.048 (2)	0.009 (2)	−0.009 (2)	−0.0144 (18)
C26	0.088 (3)	0.076 (3)	0.087 (4)	−0.025 (3)	−0.013 (3)	−0.022 (3)
C27	0.062 (2)	0.048 (2)	0.054 (2)	0.018 (2)	0.008 (2)	0.0111 (18)
C28	0.071 (3)	0.054 (2)	0.081 (3)	−0.013 (2)	0.019 (3)	0.011 (2)
C29	0.108 (4)	0.081 (3)	0.060 (3)	0.028 (3)	0.008 (3)	0.025 (3)
C30	0.0504 (19)	0.046 (2)	0.042 (2)	−0.0014 (18)	−0.0086 (17)	−0.0036 (17)

Geometric parameters (Å, º)

O1—C1	1.421 (4)	C13—C30	1.522 (5)
O1—H1A	0.820	C13—C14	1.549 (5)
O2—C16	1.328 (5)	C15—H15A	0.960
O2—C4	1.453 (4)	C15—H15B	0.960
O3—C16	1.210 (5)	C15—H15C	0.960
O4—C18	1.330 (6)	C16—C17	1.482 (7)
O4—C6	1.469 (4)	C17—H17A	0.960
O5—C18	1.205 (6)	C17—H17B	0.960
O6—C23	1.346 (5)	C17—H17C	0.960
O6—C22	1.443 (5)	C18—C19	1.511 (7)
O7—C23	1.186 (5)	C19—C20'	1.425 (16)
O8—C25	1.344 (5)	C19—C20	1.435 (15)
O8—C8	1.463 (4)	C19—H19A	0.970
O9—C25	1.200 (5)	C19—H19B	0.970
O10—C13	1.444 (4)	C20—C21	1.57 (2)
O10—H10A	0.820	C20—H20A	0.970
O11—C14	1.212 (4)	C20—H20B	0.970
C1—C14	1.519 (5)	C21—H21A	0.960
C1—C2	1.552 (5)	C21—H21B	0.960
C1—C5	1.552 (5)	C21—H21C	0.960
C2—C3	1.519 (6)	C20'—C21'	1.360 (19)
C2—H2A	0.970	C20'—H20C	0.970
C2—H2B	0.970	C20'—H20D	0.970
C3—C15	1.526 (6)	C21'—H21D	0.960
C3—C4	1.528 (5)	C21'—H21E	0.960
C3—H3	0.980	C21'—H21F	0.960
C4—C5	1.528 (5)	C22—H22A	0.970
C4—H4	0.980	C22—H22B	0.970
C5—C6	1.515 (5)	C23—C24	1.488 (6)
C5—H5	0.980	C24—H24A	0.960
C6—C7	1.572 (5)	C24—H24B	0.960
C6—H6	0.980	C24—H24C	0.960
C7—C22	1.530 (5)	C25—C26	1.485 (7)
C7—C8	1.561 (5)	C26—H26A	0.960
C7—C12	1.582 (5)	C26—H26B	0.960
C8—C9	1.475 (5)	C26—H26C	0.960
C8—H8	0.980	C27—C28	1.352 (6)
C9—C10	1.306 (6)	C27—C29	1.480 (7)
C9—H9	0.930	C28—H28A	0.930
C10—C11	1.508 (5)	C28—H28B	0.930
C10—H10	0.930	C29—H29A	0.960
C11—C27	1.533 (5)	C29—H29B	0.960
C11—C12	1.580 (5)	C29—H29C	0.960
C11—H11	0.980	C30—H30A	0.960
C12—C13	1.588 (4)	C30—H30B	0.960
C12—H12	0.980	C30—H30C	0.960
C1—O1—H1A	109.5	O3—C16—O2	124.1 (4)
C16—O2—C4	118.8 (3)	O3—C16—C17	124.8 (4)
C18—O4—C6	118.9 (3)	O2—C16—C17	111.1 (4)
C23—O6—C22	116.4 (3)	C16—C17—H17A	109.5
C25—O8—C8	116.0 (3)	C16—C17—H17B	109.5
C13—O10—H10A	109.5	H17A—C17—H17B	109.5
O1—C1—C14	111.4 (3)	C16—C17—H17C	109.5
O1—C1—C2	111.0 (3)	H17A—C17—H17C	109.5
C14—C1—C2	115.4 (3)	H17B—C17—H17C	109.5
O1—C1—C5	109.3 (3)	O5—C18—O4	124.0 (4)
C14—C1—C5	105.8 (3)	O5—C18—C19	124.8 (5)
C2—C1—C5	103.3 (3)	O4—C18—C19	111.2 (5)
C3—C2—C1	107.5 (3)	C20'—C19—C18	118.5 (8)
C3—C2—H2A	110.2	C20—C19—C18	117.6 (8)
C1—C2—H2A	110.2	C20'—C19—H19A	124.7
C3—C2—H2B	110.2	C20—C19—H19A	107.9
C1—C2—H2B	110.2	C18—C19—H19A	107.9
H2A—C2—H2B	108.5	C20'—C19—H19B	86.3
C2—C3—C15	114.9 (4)	C20—C19—H19B	107.9
C2—C3—C4	103.6 (3)	C18—C19—H19B	107.9
C15—C3—C4	115.5 (4)	H19A—C19—H19B	107.2
C2—C3—H3	107.5	C19—C20—C21	112.0 (11)
C15—C3—H3	107.5	C19—C20—H20A	109.2
C4—C3—H3	107.5	C21—C20—H20A	109.2
O2—C4—C3	109.4 (3)	C19—C20—H20B	109.2
O2—C4—C5	107.5 (3)	C21—C20—H20B	109.2
C3—C4—C5	101.7 (3)	H20A—C20—H20B	107.9
O2—C4—H4	112.5	C20—C21—H21A	109.5
C3—C4—H4	112.5	C20—C21—H21B	109.5
C5—C4—H4	112.5	H21A—C21—H21B	109.5
C6—C5—C4	116.1 (3)	C20—C21—H21C	109.5
C6—C5—C1	114.6 (3)	H21A—C21—H21C	109.5
C4—C5—C1	104.0 (3)	H21B—C21—H21C	109.5
C6—C5—H5	107.2	C21'—C20'—C19	111.8 (13)
C4—C5—H5	107.2	C21'—C20'—H20C	109.3
C1—C5—H5	107.2	C19—C20'—H20C	109.3
O4—C6—C5	103.8 (3)	C21'—C20'—H20D	109.3
O4—C6—C7	105.8 (3)	C19—C20'—H20D	109.3
C5—C6—C7	119.9 (3)	H20C—C20'—H20D	107.9
O4—C6—H6	108.9	C20'—C21'—H21D	109.5
C5—C6—H6	108.9	C20'—C21'—H21E	109.5
C7—C6—H6	108.9	H21D—C21'—H21E	109.5
C22—C7—C8	103.6 (3)	C20'—C21'—H21F	109.5
C22—C7—C6	112.9 (3)	H21D—C21'—H21F	109.5
C8—C7—C6	104.2 (3)	H21E—C21'—H21F	109.5
C22—C7—C12	113.7 (3)	O6—C22—C7	109.8 (3)
C8—C7—C12	107.8 (3)	O6—C22—H22A	109.7
C6—C7—C12	113.5 (3)	C7—C22—H22A	109.7
O8—C8—C9	109.4 (3)	O6—C22—H22B	109.7
O8—C8—C7	106.8 (3)	C7—C22—H22B	109.7
C9—C8—C7	113.8 (3)	H22A—C22—H22B	108.2
O8—C8—H8	108.9	O7—C23—O6	121.6 (4)
C9—C8—H8	108.9	O7—C23—C24	126.5 (4)
C7—C8—H8	108.9	O6—C23—C24	111.8 (4)
C10—C9—C8	119.8 (3)	C23—C24—H24A	109.5
C10—C9—H9	120.1	C23—C24—H24B	109.5
C8—C9—H9	120.1	H24A—C24—H24B	109.5
C9—C10—C11	125.0 (4)	C23—C24—H24C	109.5
C9—C10—H10	117.5	H24A—C24—H24C	109.5
C11—C10—H10	117.5	H24B—C24—H24C	109.5
C10—C11—C27	107.2 (3)	O9—C25—O8	123.5 (4)
C10—C11—C12	115.9 (3)	O9—C25—C26	125.3 (4)
C27—C11—C12	114.0 (3)	O8—C25—C26	111.2 (4)
C10—C11—H11	106.4	C25—C26—H26A	109.5
C27—C11—H11	106.4	C25—C26—H26B	109.5
C12—C11—H11	106.4	H26A—C26—H26B	109.5
C11—C12—C7	113.1 (3)	C25—C26—H26C	109.5
C11—C12—C13	108.2 (3)	H26A—C26—H26C	109.5
C7—C12—C13	119.2 (3)	H26B—C26—H26C	109.5
C11—C12—H12	105.0	C28—C27—C29	122.1 (4)
C7—C12—H12	105.0	C28—C27—C11	120.3 (4)
C13—C12—H12	105.0	C29—C27—C11	117.6 (4)
O10—C13—C30	109.2 (3)	C27—C28—H28A	120.0
O10—C13—C14	101.4 (3)	C27—C28—H28B	120.0
C30—C13—C14	108.8 (3)	H28A—C28—H28B	120.0
O10—C13—C12	103.8 (3)	C27—C29—H29A	109.5
C30—C13—C12	115.3 (3)	C27—C29—H29B	109.5
C14—C13—C12	117.0 (3)	H29A—C29—H29B	109.5
O11—C14—C1	119.8 (3)	C27—C29—H29C	109.5
O11—C14—C13	120.9 (3)	H29A—C29—H29C	109.5
C1—C14—C13	119.2 (3)	H29B—C29—H29C	109.5
C3—C15—H15A	109.5	C13—C30—H30A	109.5
C3—C15—H15B	109.5	C13—C30—H30B	109.5
H15A—C15—H15B	109.5	H30A—C30—H30B	109.5
C3—C15—H15C	109.5	C13—C30—H30C	109.5
H15A—C15—H15C	109.5	H30A—C30—H30C	109.5
H15B—C15—H15C	109.5	H30B—C30—H30C	109.5
O1—C1—C2—C3	−114.4 (3)	C27—C11—C12—C13	85.7 (4)
C14—C1—C2—C3	117.6 (4)	C22—C7—C12—C11	−69.3 (4)
C5—C1—C2—C3	2.7 (4)	C8—C7—C12—C11	44.9 (4)
C1—C2—C3—C15	150.9 (4)	C6—C7—C12—C11	159.8 (3)
C1—C2—C3—C4	24.0 (4)	C22—C7—C12—C13	59.5 (4)
C16—O2—C4—C3	108.6 (4)	C8—C7—C12—C13	173.8 (3)
C16—O2—C4—C5	−141.7 (3)	C6—C7—C12—C13	−71.3 (4)
C2—C3—C4—O2	72.0 (4)	C11—C12—C13—O10	−78.3 (3)
C15—C3—C4—O2	−54.5 (4)	C7—C12—C13—O10	150.7 (3)
C2—C3—C4—C5	−41.5 (4)	C11—C12—C13—C30	41.1 (4)
C15—C3—C4—C5	−167.9 (3)	C7—C12—C13—C30	−90.0 (4)
O2—C4—C5—C6	55.4 (4)	C11—C12—C13—C14	171.0 (3)
C3—C4—C5—C6	170.4 (3)	C7—C12—C13—C14	40.0 (4)
O2—C4—C5—C1	−71.4 (3)	O1—C1—C14—O11	−148.0 (3)
C3—C4—C5—C1	43.6 (3)	C2—C1—C14—O11	−20.3 (5)
O1—C1—C5—C6	−37.9 (4)	C5—C1—C14—O11	93.3 (4)
C14—C1—C5—C6	82.1 (3)	O1—C1—C14—C13	31.1 (4)
C2—C1—C5—C6	−156.2 (3)	C2—C1—C14—C13	158.8 (3)
O1—C1—C5—C4	89.8 (3)	C5—C1—C14—C13	−87.6 (3)
C14—C1—C5—C4	−150.1 (3)	O10—C13—C14—O11	102.1 (4)
C2—C1—C5—C4	−28.4 (3)	C30—C13—C14—O11	−12.9 (5)
C18—O4—C6—C5	−110.1 (4)	C12—C13—C14—O11	−145.9 (4)
C18—O4—C6—C7	122.7 (3)	O10—C13—C14—C1	−77.0 (3)
C4—C5—C6—O4	57.3 (4)	C30—C13—C14—C1	168.0 (3)
C1—C5—C6—O4	178.6 (3)	C12—C13—C14—C1	35.1 (4)
C4—C5—C6—C7	175.1 (3)	C4—O2—C16—O3	−1.7 (6)
C1—C5—C6—C7	−63.6 (4)	C4—O2—C16—C17	177.8 (4)
O4—C6—C7—C22	47.5 (4)	C6—O4—C18—O5	−10.2 (6)
C5—C6—C7—C22	−69.3 (4)	C6—O4—C18—C19	169.4 (4)
O4—C6—C7—C8	−64.2 (3)	O5—C18—C19—C20'	−58.9 (11)
C5—C6—C7—C8	179.0 (3)	O4—C18—C19—C20'	121.5 (8)
O4—C6—C7—C12	178.7 (3)	O5—C18—C19—C20	−32.2 (11)
C5—C6—C7—C12	62.0 (4)	O4—C18—C19—C20	148.2 (8)
C25—O8—C8—C9	−84.4 (4)	C20'—C19—C20—C21	27 (2)
C25—O8—C8—C7	152.1 (3)	C18—C19—C20—C21	−71.0 (13)
C22—C7—C8—O8	−175.5 (3)	C20—C19—C20'—C21'	−155 (4)
C6—C7—C8—O8	−57.2 (3)	C18—C19—C20'—C21'	−60.4 (15)
C12—C7—C8—O8	63.7 (3)	C23—O6—C22—C7	169.2 (3)
C22—C7—C8—C9	63.8 (4)	C8—C7—C22—O6	170.2 (3)
C6—C7—C8—C9	−178.0 (3)	C6—C7—C22—O6	58.1 (4)
C12—C7—C8—C9	−57.0 (4)	C12—C7—C22—O6	−73.1 (4)
O8—C8—C9—C10	−82.7 (4)	C22—O6—C23—O7	−1.7 (7)
C7—C8—C9—C10	36.6 (5)	C22—O6—C23—C24	176.6 (4)
C8—C9—C10—C11	−1.5 (6)	C8—O8—C25—O9	1.9 (5)
C9—C10—C11—C27	119.2 (4)	C8—O8—C25—C26	−178.0 (4)
C9—C10—C11—C12	−9.3 (6)	C10—C11—C27—C28	−59.9 (5)
C10—C11—C12—C7	−14.9 (4)	C12—C11—C27—C28	69.7 (5)
C27—C11—C12—C7	−140.0 (3)	C10—C11—C27—C29	117.2 (4)
C10—C11—C12—C13	−149.2 (3)	C12—C11—C27—C29	−113.2 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O10	0.82	2.24	2.815 (4)	127
O10—H10A···O3^i	0.82	2.03	2.812 (4)	159

Symmetry code: (i) −x+1/2, −y+1, z+1/2.