Crystal structures of (±)-(1SR,5SR,6SR,7SR,10SR,11SR,13RS,14SR)-13-hy­droxy-7-meth­oxy­meth­oxy-11,15,18,18-tetra­methyl-3-oxo-2,4-dioxa­tetra­cyclo­[12.3.1.01,5.06,11]octa­dec-15-en-10-yl benzoate, its 13-epimer and 13-one derivative

Oishi, T.; Fukaya, K.; Yamaguchi, Y.; Sugai, T.; Watanabe, A.; Sato, T.; Chida, N.

doi:10.1107/S2056989015006854

Crystal structures of (±)-(1SR,5SR,6SR,7SR,10SR,11SR,13RS,14SR)-13-hydroxy-7-methoxymethoxy-11,15,18,18-tetramethyl-3-oxo-2,4-dioxatetracyclo[12.3.1.0^1,5.0^6,11]octadec-15-en-10-yl benzoate, its 13-epimer and 13-one derivative

T. Oishi, K. Fukaya, Y. Yamaguchi, T. Sugai, A. Watanabe, T. Sato and N. Chida

In the title three compounds, the ring conformations of tetracycles are similar; each tetracycle adopts essentially planar, chair, half-chair and chair–chair forms. In the crystals, molecules are linked into similar chains by intermolecular hydrogen bonds.

Keywords: crystal structure; hydrogen bonds; taxane skeleton; paclitaxel.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015006854/is5395sup1.cif Contains datablocks global, A, B, C
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989015006854/is5395Asup2.hkl Contains datablock A
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989015006854/is5395Bsup3.hkl Contains datablock B
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989015006854/is5395Csup4.hkl Contains datablock C

CCDC references: 1057985; 1057984; 1057983

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Key indicators

Structure: A

Single-crystal X-ray study
T = 90 K
Mean (C-C) = 0.003 Å
Disorder in solvent or counterion
R factor = 0.040
wR factor = 0.099
Data-to-parameter ratio = 13.4

Structure: B

Single-crystal X-ray study
T = 90 K
Mean (C-C) = 0.003 Å
R factor = 0.043
wR factor = 0.111
Data-to-parameter ratio = 13.2

Structure: C

Single-crystal X-ray study
T = 90 K
Mean (C-C) = 0.003 Å
R factor = 0.044
wR factor = 0.105
Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Datablock: A


Alert level C
PLAT410_ALERT_2_C Short Intra H...H Contact  H2     ..  H10     ..       1.93 Ang.
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Th(Min) ...          7 Report
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.595         62 Report

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT045_ALERT_1_G Calculated and Reported Z Differ by ............       0.25 Ratio
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT300_ALERT_4_G Atom Site Occupancy of *C1P    is Constrained at      0.500 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *C2P    is Constrained at      0.500 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *C3P    is Constrained at      0.500 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *C4P    is Constrained at      0.500 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *C5P    is Constrained at      0.500 Check
PLAT302_ALERT_4_G Anion/Solvent Disorder ............ Percentage =        100 Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms (   8.50) in Resd. #          3 Check
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........         18 Note
PLAT789_ALERT_4_G Atoms with Negative _atom_site_disorder_group  #         17 Check
PLAT793_ALERT_4_G The Model has Chirality at C1      (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C1'     (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C2      (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C2'     (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C3      (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C3'     (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C4      (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C4'     (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C7      (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C7'     (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C8      (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C8'     (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C10     (Centro SPGR)          R Verify
PLAT793_ALERT_4_G The Model has Chirality at C10'    (Centro SPGR)          R Verify
PLAT793_ALERT_4_G The Model has Chirality at C11     (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C11'    (Centro SPGR)          S Verify
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still          51 %

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
  25 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check




Datablock: B


Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.41 Report
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.712 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.595         20 Report

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT343_ALERT_2_G Unusual sp3      Angle Range in Main Residue for     C9     Check
PLAT793_ALERT_4_G The Model has Chirality at C1      (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C2      (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C3      (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C4      (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C7      (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C8      (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C10     (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C11     (Centro SPGR)          S Verify
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still          43 %
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ...          3 Report

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

   1 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
   4 ALERT type 3 Indicator that the structure quality may be low
   8 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check




Datablock: C


Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O23    --  C21     ..        5.4 su
PLAT412_ALERT_2_C Short Intra XH3 .. XHn     H2     ..  H16A    ..       1.88 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H14A   ..  O34     ..       2.65 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.960 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.595         35 Report

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT432_ALERT_2_G Short Inter X...Y Contact  O36    ..  C25     ..       3.01 Ang.
PLAT793_ALERT_4_G The Model has Chirality at C1      (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C2      (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C3      (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C4      (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C7      (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C8      (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C11     (Centro SPGR)          S Verify
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still          39 %
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ...          3 Report

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

   0 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
   4 ALERT type 3 Indicator that the structure quality may be low
   8 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

Author Response: Contributions and roles for this paper are following; Oishi, T. : X-ray analysis and description for the paper. Yamaguchi, Y., Fukaya, K., Sugai, T., Watanabe, A., Sato, T. and Chida, N.; Synthesis (linear 26 and more steps from 3-methylanisole), purification, crystallization and other spectroscopic characterization of the title compounds.


   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

For all compounds, data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010) and PLATON (Spek, 2009).

(A) (±)-(1SR,5SR,6SR,7SR,10SR,11SR,13RS,14SR)-13-Hydroxy-7-methoxymethoxy-11,15,18,18-tetramethyl-3-oxo-2,4-dioxatetracyclo[12.3.1.0^1,5.0^6,11]octadec-15-en-10-yl benzoate pentane 0.25-solvate top

Crystal data top

C₂₉H₃₈O₈·0.25C₅H₁₂	F(000) = 1146
M_r = 532.64	D_x = 1.277 Mg m⁻³
Triclinic, P1	Melting point: 509.2 K
a = 11.3343 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 15.4666 (7) Å	Cell parameters from 9428 reflections
c = 16.4870 (8) Å	θ = 2.4–25.0°
α = 85.1124 (14)°	µ = 0.09 mm⁻¹
β = 78.3773 (14)°	T = 90 K
γ = 78.5231 (15)°	Prism, colorless
V = 2771.3 (2) Å³	0.32 × 0.21 × 0.17 mm
Z = 4

Data collection top

Bruker D8 Venture diffractometer	9735 independent reflections
Radiation source: fine-focus sealed tube	7339 reflections with I > 2σ(I)
Multilayered confocal mirror monochromator	R_int = 0.041
Detector resolution: 8.333 pixels mm^-1	θ_max = 25.0°, θ_min = 2.2°
φ and ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −18→18
T_min = 0.97, T_max = 0.98	l = −19→19
50997 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.039P)² + 1.4256P] where P = (F_o² + 2F_c²)/3
9735 reflections	(Δ/σ)_max = 0.008
726 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Special details top

Experimental. M.p. 507.2–509.2 K (not corrected); IR (film) 3502, 2950, 1799, 1717, 1451, 1272, 1098, 1055, 713 cm^-1; ¹H NMR (500 MHz, CDCl₃) δ (p.p.m.) 8.03–8.00 (m, 2H), 7.60–7.55 (m, 1H), 7.48–7.43 (m, 2H), 5.50 (bs, 1H), 4.78 (d, J = 7.2 Hz, 1H), 4.71 (dd, J = 11.3, 4.3 Hz, 1H), 4.58 (d, J = 7.2 Hz, 1H), 4.50 (d, J = 3.7 Hz, 1H), 4.31 (dd, J = 9.0, 2.0 Hz, 1H), 3.56 (ddd, J = 10.7, 10.7, 5.2 Hz, 1H), 3.35 (s, 3H), 2.87 (bd, J = 18.3 Hz, 1H), 2.41–2.30 (m, 2H), 2.11 (s, 1H), 2.08 (dd, J = 10.7, 3.7 Hz, 1H), 1.89 (dddd, J = 12.7, 4.3, 4.0, 4.0 Hz, 1H), 1.77 (s, 3H), 1.72–1.50 (m, 4H), 1.29 (s, 3H), 1.25 (s, 3H), 1.17 (s, 3H); ¹³C NMR (125 MHz, CDCl₃) δ (p.p.m.) 165.9 (C), 154.1 (C), 136.7 (C), 133.4 (CH), 130.3 (C), 129.7 (CH), 128.6 (CH), 120.9 (CH), 97.8 (CH₂), 87.1 (C), 80.0 (CH), 78.1 (CH), 75.0 (CH), 67.1 (CH), 60.6 (CH), 55.9 (CH₃), 47.8 (CH₂), 46.2 (CH), 42.6 (C), 40.2 (C), 31.9 (CH₂), 31.2 (CH₂), 25.9 (CH₃), 25.1 (CH₃), 24.7 (CH₂), 19.8 (CH₃), 13.6 (CH₃); LRMS (EI) m/z 514 (M⁺, 4%), 483 (1), 469 (1), 453 (1), 409 (4), 393 (12), 348 (1), 332 (1), 121 (83), 105 (100), 77 (67); HRMS (EI) m/z calcd for C₂₉H₃₈O₈⁺ [M]⁺ 514.2567, found 514.2545.

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.

Problematic three reflections with |I(obs)-I(calc)|/σW(I) greater than 10 (1 1 0, 9 9 11 and 5 3 11) have been omitted in the final refinement.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.39192 (15)	0.71883 (11)	0.80546 (10)	0.0182 (4)
C2	0.29323 (15)	0.76771 (11)	0.87419 (10)	0.0178 (4)
H2	0.2366	0.8123	0.8455	0.021*
C3	0.33237 (15)	0.81694 (11)	0.93856 (10)	0.0167 (4)
H3	0.4227	0.8146	0.9212	0.02*
C4	0.31165 (16)	0.77206 (11)	1.02534 (11)	0.0199 (4)
H4	0.2234	0.767	1.0428	0.024*
C5	0.34803 (17)	0.82311 (11)	1.08803 (11)	0.0228 (4)
H5A	0.4373	0.8225	1.0739	0.027*
H5B	0.3297	0.7943	1.1439	0.027*
C6	0.27850 (17)	0.91845 (11)	1.08866 (11)	0.0231 (4)
H6A	0.1893	0.9196	1.1049	0.028*
H6B	0.3035	0.9513	1.1293	0.028*
C7	0.30713 (16)	0.96120 (11)	1.00303 (10)	0.0192 (4)
H7	0.3973	0.9604	0.9885	0.023*
C8	0.27009 (15)	0.91625 (11)	0.93435 (10)	0.0169 (4)
C9	0.32337 (16)	0.96195 (11)	0.85154 (10)	0.0196 (4)
H9B	0.285	1.0253	0.8542	0.024*
H9A	0.4116	0.9585	0.8511	0.024*
C10	0.31409 (16)	0.93271 (11)	0.76616 (10)	0.0196 (4)
H10	0.2326	0.9153	0.7703	0.024*
C11	0.41687 (15)	0.85809 (11)	0.72360 (10)	0.0184 (4)
H11	0.4345	0.8795	0.6642	0.022*
C12	0.53785 (16)	0.85012 (11)	0.75254 (10)	0.0201 (4)
C13	0.58295 (16)	0.77927 (11)	0.79574 (11)	0.0211 (4)
H13	0.659	0.7782	0.812	0.025*
C14	0.52260 (15)	0.70092 (11)	0.82067 (11)	0.0201 (4)
H14A	0.522	0.6854	0.8802	0.024*
H14B	0.5706	0.6499	0.7888	0.024*
C15	0.38464 (15)	0.76528 (11)	0.72002 (10)	0.0191 (4)
C16	0.25946 (16)	0.77064 (12)	0.69574 (11)	0.0225 (4)
H16A	0.1941	0.7916	0.7423	0.034*
H16B	0.2515	0.712	0.6819	0.034*
H16C	0.2529	0.8118	0.6476	0.034*
C17	0.47951 (17)	0.71477 (12)	0.65165 (11)	0.0237 (4)
H17B	0.4675	0.742	0.5973	0.036*
H17C	0.4692	0.6531	0.6547	0.036*
H17A	0.5623	0.7171	0.6594	0.036*
C18	0.60684 (17)	0.92447 (12)	0.72667 (12)	0.0278 (4)
H18A	0.6397	0.9233	0.667	0.042*
H18B	0.6745	0.9177	0.7569	0.042*
H18C	0.5513	0.9809	0.7392	0.042*
C19	0.13055 (15)	0.92911 (11)	0.94717 (11)	0.0214 (4)
H19C	0.1076	0.9005	0.9034	0.032*
H19A	0.0958	0.9924	0.945	0.032*
H19B	0.0988	0.9027	1.0013	0.032*
O20	0.22400 (11)	0.70057 (8)	0.91336 (7)	0.0214 (3)
C21	0.26240 (16)	0.62580 (12)	0.87360 (11)	0.0216 (4)
O22	0.35432 (11)	0.63298 (7)	0.80929 (7)	0.0215 (3)
O23	0.22106 (12)	0.56013 (8)	0.89208 (8)	0.0298 (3)
O24	0.24272 (10)	1.05356 (7)	1.00196 (7)	0.0201 (3)
C25	0.30152 (16)	1.11360 (11)	1.02153 (10)	0.0197 (4)
O26	0.39773 (11)	1.09511 (8)	1.04546 (8)	0.0283 (3)
C27	0.23598 (16)	1.20589 (11)	1.01040 (10)	0.0194 (4)
C28	0.29728 (17)	1.27379 (12)	1.01677 (11)	0.0231 (4)
H28	0.3782	1.2602	1.0278	0.028*
C29	0.24120 (18)	1.36072 (12)	1.00719 (11)	0.0272 (4)
H29	0.2837	1.4068	1.0113	0.033*
C30	0.12343 (18)	1.38076 (12)	0.99168 (11)	0.0275 (4)
H30	0.0847	1.4407	0.9855	0.033*
C31	0.06173 (17)	1.31401 (12)	0.98513 (12)	0.0276 (4)
H31	−0.0195	1.3281	0.9748	0.033*
C32	0.11788 (16)	1.22643 (12)	0.99364 (11)	0.0226 (4)
H32	0.0758	1.1806	0.988	0.027*
O33	0.32219 (12)	1.00634 (8)	0.70805 (8)	0.0276 (3)
H33	0.2664	1.049	0.7246	0.041*
O34	0.38701 (11)	0.68492 (7)	1.01813 (7)	0.0218 (3)
C35	0.33439 (17)	0.61646 (12)	1.06299 (11)	0.0248 (4)
H35A	0.2477	0.625	1.0568	0.03*
H35B	0.3774	0.5597	1.0387	0.03*
O36	0.33867 (12)	0.61094 (8)	1.14683 (7)	0.0288 (3)
C37	0.4588 (2)	0.58010 (15)	1.16272 (15)	0.0452 (6)
H37B	0.5132	0.6193	1.1335	0.068*
H37C	0.489	0.5201	1.1432	0.068*
H37A	0.457	0.5795	1.2224	0.068*
C1'	0.80525 (16)	0.74195 (11)	0.31038 (11)	0.0190 (4)
C2'	0.90913 (15)	0.67289 (11)	0.26359 (10)	0.0185 (4)
H2'	0.8711	0.6423	0.2274	0.022*
C3'	0.98195 (15)	0.60049 (11)	0.31378 (10)	0.0182 (4)
H3'	0.9397	0.6052	0.3731	0.022*
C4'	1.11310 (16)	0.61437 (11)	0.30982 (11)	0.0225 (4)
H4'	1.1551	0.6192	0.2506	0.027*
C5'	1.18605 (17)	0.53955 (12)	0.35504 (12)	0.0274 (4)
H5'A	1.1505	0.5397	0.415	0.033*
H5'B	1.2718	0.5483	0.3478	0.033*
C6'	1.18424 (17)	0.45122 (12)	0.32163 (12)	0.0265 (4)
H6'A	1.2218	0.4501	0.262	0.032*
H6'B	1.2321	0.4028	0.3514	0.032*
C7'	1.05332 (16)	0.43877 (11)	0.33368 (11)	0.0216 (4)
H7'	1.0172	0.4405	0.3942	0.026*
C8'	0.97153 (15)	0.50882 (11)	0.28678 (10)	0.0188 (4)
C9'	0.83902 (16)	0.49154 (11)	0.31629 (11)	0.0205 (4)
H9'A	0.8245	0.4886	0.3776	0.025*
H9'B	0.84	0.4314	0.2995	0.025*
C10'	0.72291 (15)	0.55088 (11)	0.29171 (11)	0.0193 (4)
H10'	0.7401	0.5667	0.2309	0.023*
C11'	0.66133 (16)	0.63631 (11)	0.33978 (10)	0.0189 (4)
H11'	0.5715	0.6377	0.3454	0.023*
C12'	0.68111 (15)	0.62936 (11)	0.42879 (11)	0.0191 (4)
C13'	0.74589 (16)	0.68057 (11)	0.45440 (11)	0.0211 (4)
H13'	0.7548	0.6732	0.5108	0.025*
C14'	0.80599 (16)	0.74896 (12)	0.40147 (11)	0.0220 (4)
H14D	0.8917	0.7418	0.4094	0.026*
H14E	0.7625	0.8084	0.4191	0.026*
C15'	0.67950 (16)	0.72807 (11)	0.29790 (11)	0.0199 (4)
C16'	0.66754 (17)	0.73683 (12)	0.20653 (11)	0.0237 (4)
H16D	0.7362	0.6974	0.1743	0.036*
H16E	0.6686	0.798	0.1857	0.036*
H16F	0.5902	0.7207	0.2012	0.036*
C17'	0.57506 (16)	0.79806 (11)	0.34144 (12)	0.0237 (4)
H17D	0.5714	0.7911	0.4015	0.036*
H17E	0.497	0.7904	0.3288	0.036*
H17F	0.5903	0.8572	0.3218	0.036*
C18'	0.61846 (17)	0.56509 (12)	0.48620 (11)	0.0264 (4)
H18D	0.5294	0.5838	0.4921	0.04*
H18E	0.6417	0.5631	0.5406	0.04*
H18F	0.6433	0.5063	0.4635	0.04*
C19'	1.01302 (17)	0.49893 (12)	0.19299 (11)	0.0237 (4)
H19D	1.0253	0.4366	0.1806	0.035*
H19E	1.0902	0.5205	0.1742	0.035*
H19F	0.9501	0.5335	0.1642	0.035*
O20'	0.98878 (11)	0.72516 (7)	0.20899 (7)	0.0218 (3)
C21'	0.93856 (16)	0.81059 (12)	0.21184 (11)	0.0219 (4)
O22'	0.83303 (11)	0.82463 (7)	0.26720 (7)	0.0230 (3)
O23'	0.98135 (12)	0.86793 (8)	0.17053 (8)	0.0291 (3)
O24'	1.05092 (11)	0.35259 (7)	0.30544 (7)	0.0232 (3)
C25'	1.05285 (16)	0.28473 (12)	0.36162 (11)	0.0230 (4)
O26'	1.05309 (14)	0.29155 (9)	0.43359 (8)	0.0366 (4)
C27'	1.05285 (16)	0.20029 (11)	0.32452 (11)	0.0226 (4)
C28'	1.03407 (19)	0.12820 (13)	0.37777 (13)	0.0328 (5)
H28'	1.0236	0.1332	0.4359	0.039*
C29'	1.0305 (2)	0.04866 (13)	0.34638 (14)	0.0403 (5)
H29'	1.0167	−0.0006	0.3831	0.048*
C30'	1.04693 (18)	0.04084 (13)	0.26221 (13)	0.0343 (5)
H30'	1.044	−0.0137	0.2409	0.041*
C31'	1.06757 (16)	0.11189 (12)	0.20896 (12)	0.0270 (4)
H31'	1.0804	0.1059	0.1508	0.032*
C32'	1.06975 (15)	0.19203 (12)	0.23947 (11)	0.0231 (4)
H32'	1.0828	0.2412	0.2024	0.028*
O33'	0.62847 (11)	0.49828 (8)	0.30885 (8)	0.0254 (3)
H33'	0.6435	0.4595	0.2736	0.038*
O34'	1.09963 (11)	0.69699 (8)	0.34778 (8)	0.0255 (3)
C35'	1.1978 (2)	0.74151 (14)	0.32338 (13)	0.0370 (5)
H35D	1.2264	0.7375	0.2628	0.044*
H35F	1.1685	0.8047	0.335	0.044*
O36'	1.29654 (12)	0.70912 (10)	0.36255 (10)	0.0446 (4)
C37'	1.2687 (2)	0.72296 (17)	0.44817 (15)	0.0529 (7)
H37D	1.3415	0.6998	0.4725	0.079*
H37E	1.2021	0.6923	0.4747	0.079*
H37F	1.2432	0.7864	0.4569	0.079*
C1P	0.2437 (5)	0.9991 (4)	0.5096 (4)	0.0466 (14)	0.5
H1PA	0.2192	1.0095	0.569	0.07*	0.5
H1PB	0.1943	0.9599	0.4945	0.07*	0.5
H1PC	0.2307	1.0555	0.4777	0.07*	0.5
C2P	0.3778 (6)	0.9566 (6)	0.4905 (6)	0.0345 (17)	0.5
H2PA	0.4002	0.942	0.4314	0.041*	0.5
H2PB	0.3906	0.9007	0.5242	0.041*	0.5
C3P	0.4624 (5)	1.0156 (5)	0.5077 (5)	0.036 (3)	0.5
H3PA	0.4536	1.0696	0.471	0.043*	0.5
H3PB	0.4357	1.0338	0.5656	0.043*	0.5
C4P	0.5962 (7)	0.9719 (8)	0.4947 (7)	0.044 (2)	0.5
H4PA	0.6228	0.9528	0.437	0.053*	0.5
H4PB	0.6055	0.9184	0.5322	0.053*	0.5
C5P	0.6788 (7)	1.0321 (6)	0.5108 (6)	0.047 (2)	0.5
H5PA	0.6741	1.0834	0.4715	0.07*	0.5
H5PB	0.7636	0.9998	0.5038	0.07*	0.5
H5PC	0.6521	1.0522	0.5675	0.07*	0.5

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0196 (9)	0.0124 (9)	0.0231 (9)	−0.0029 (7)	−0.0042 (7)	−0.0035 (7)
C2	0.0196 (9)	0.0145 (9)	0.0193 (9)	−0.0040 (7)	−0.0026 (7)	−0.0005 (7)
C3	0.0138 (9)	0.0148 (9)	0.0206 (9)	−0.0020 (7)	−0.0009 (7)	−0.0039 (7)
C4	0.0203 (10)	0.0151 (9)	0.0226 (10)	−0.0024 (7)	−0.0008 (8)	−0.0021 (7)
C5	0.0287 (11)	0.0216 (10)	0.0192 (9)	−0.0069 (8)	−0.0045 (8)	−0.0011 (8)
C6	0.0247 (10)	0.0228 (10)	0.0223 (10)	−0.0053 (8)	−0.0021 (8)	−0.0077 (8)
C7	0.0174 (9)	0.0146 (9)	0.0248 (10)	−0.0008 (7)	−0.0030 (8)	−0.0042 (7)
C8	0.0149 (9)	0.0166 (9)	0.0186 (9)	−0.0031 (7)	−0.0010 (7)	−0.0029 (7)
C9	0.0190 (9)	0.0154 (9)	0.0241 (10)	−0.0014 (7)	−0.0038 (8)	−0.0037 (7)
C10	0.0195 (9)	0.0159 (9)	0.0219 (9)	−0.0012 (7)	−0.0034 (7)	0.0019 (7)
C11	0.0189 (9)	0.0188 (9)	0.0163 (9)	−0.0027 (7)	−0.0013 (7)	−0.0010 (7)
C12	0.0188 (9)	0.0220 (10)	0.0183 (9)	−0.0031 (7)	0.0001 (7)	−0.0049 (8)
C13	0.0153 (9)	0.0255 (10)	0.0219 (9)	−0.0019 (7)	−0.0030 (7)	−0.0048 (8)
C14	0.0200 (10)	0.0172 (9)	0.0211 (9)	0.0022 (7)	−0.0035 (8)	−0.0035 (7)
C15	0.0185 (9)	0.0194 (9)	0.0188 (9)	−0.0027 (7)	−0.0025 (7)	−0.0033 (7)
C16	0.0255 (10)	0.0225 (10)	0.0209 (9)	−0.0042 (8)	−0.0070 (8)	−0.0026 (8)
C17	0.0263 (10)	0.0220 (10)	0.0220 (10)	−0.0020 (8)	−0.0038 (8)	−0.0044 (8)
C18	0.0232 (10)	0.0267 (11)	0.0327 (11)	−0.0050 (8)	−0.0034 (8)	−0.0006 (9)
C19	0.0178 (9)	0.0188 (9)	0.0269 (10)	−0.0013 (7)	−0.0025 (8)	−0.0071 (8)
O20	0.0205 (7)	0.0192 (7)	0.0249 (7)	−0.0077 (5)	0.0003 (5)	−0.0052 (5)
C21	0.0230 (10)	0.0206 (10)	0.0225 (10)	−0.0041 (8)	−0.0071 (8)	−0.0023 (8)
O22	0.0245 (7)	0.0153 (6)	0.0241 (7)	−0.0046 (5)	−0.0015 (6)	−0.0038 (5)
O23	0.0360 (8)	0.0211 (7)	0.0353 (8)	−0.0141 (6)	−0.0050 (6)	−0.0013 (6)
O24	0.0193 (6)	0.0147 (6)	0.0271 (7)	−0.0027 (5)	−0.0042 (5)	−0.0065 (5)
C25	0.0187 (10)	0.0205 (10)	0.0204 (9)	−0.0044 (8)	−0.0021 (8)	−0.0051 (7)
O26	0.0252 (8)	0.0221 (7)	0.0403 (8)	−0.0016 (6)	−0.0127 (6)	−0.0069 (6)
C27	0.0233 (10)	0.0180 (9)	0.0158 (9)	−0.0026 (7)	−0.0012 (7)	−0.0033 (7)
C28	0.0240 (10)	0.0229 (10)	0.0236 (10)	−0.0040 (8)	−0.0059 (8)	−0.0054 (8)
C29	0.0372 (12)	0.0194 (10)	0.0271 (10)	−0.0077 (8)	−0.0070 (9)	−0.0044 (8)
C30	0.0347 (12)	0.0173 (10)	0.0254 (10)	0.0029 (8)	−0.0011 (9)	−0.0009 (8)
C31	0.0184 (10)	0.0287 (11)	0.0314 (11)	0.0018 (8)	−0.0019 (8)	0.0013 (9)
C32	0.0212 (10)	0.0233 (10)	0.0233 (10)	−0.0071 (8)	−0.0011 (8)	−0.0018 (8)
O33	0.0342 (8)	0.0182 (7)	0.0259 (7)	0.0014 (6)	−0.0026 (6)	0.0019 (6)
O34	0.0255 (7)	0.0151 (6)	0.0237 (7)	−0.0036 (5)	−0.0030 (5)	0.0006 (5)
C35	0.0298 (11)	0.0187 (10)	0.0274 (10)	−0.0073 (8)	−0.0076 (8)	0.0029 (8)
O36	0.0321 (8)	0.0298 (7)	0.0229 (7)	−0.0051 (6)	−0.0048 (6)	0.0051 (6)
C37	0.0452 (14)	0.0441 (14)	0.0534 (15)	−0.0124 (11)	−0.0287 (12)	0.0146 (11)
C1'	0.0211 (10)	0.0112 (9)	0.0243 (10)	−0.0038 (7)	−0.0033 (8)	0.0000 (7)
C2'	0.0175 (9)	0.0180 (9)	0.0209 (9)	−0.0068 (7)	−0.0034 (7)	0.0008 (7)
C3'	0.0185 (9)	0.0171 (9)	0.0181 (9)	−0.0020 (7)	−0.0031 (7)	−0.0003 (7)
C4'	0.0204 (10)	0.0221 (10)	0.0261 (10)	−0.0044 (8)	−0.0056 (8)	−0.0031 (8)
C5'	0.0193 (10)	0.0299 (11)	0.0341 (11)	−0.0042 (8)	−0.0097 (8)	0.0017 (9)
C6'	0.0237 (10)	0.0219 (10)	0.0318 (11)	0.0030 (8)	−0.0085 (8)	0.0011 (8)
C7'	0.0242 (10)	0.0176 (9)	0.0224 (10)	−0.0009 (7)	−0.0048 (8)	−0.0031 (7)
C8'	0.0189 (9)	0.0175 (9)	0.0199 (9)	−0.0019 (7)	−0.0043 (7)	−0.0022 (7)
C9'	0.0240 (10)	0.0144 (9)	0.0238 (10)	−0.0033 (7)	−0.0053 (8)	−0.0034 (7)
C10'	0.0207 (10)	0.0168 (9)	0.0221 (9)	−0.0063 (7)	−0.0045 (8)	−0.0030 (7)
C11'	0.0170 (9)	0.0172 (9)	0.0231 (9)	−0.0039 (7)	−0.0032 (7)	−0.0038 (7)
C12'	0.0179 (9)	0.0163 (9)	0.0214 (9)	−0.0003 (7)	−0.0010 (7)	−0.0039 (7)
C13'	0.0213 (10)	0.0232 (10)	0.0181 (9)	−0.0021 (8)	−0.0031 (8)	−0.0043 (8)
C14'	0.0216 (10)	0.0195 (10)	0.0260 (10)	−0.0042 (7)	−0.0041 (8)	−0.0067 (8)
C15'	0.0202 (10)	0.0153 (9)	0.0245 (10)	−0.0023 (7)	−0.0047 (8)	−0.0042 (7)
C16'	0.0235 (10)	0.0203 (10)	0.0271 (10)	−0.0014 (8)	−0.0074 (8)	0.0002 (8)
C17'	0.0211 (10)	0.0181 (10)	0.0319 (11)	−0.0022 (7)	−0.0052 (8)	−0.0039 (8)
C18'	0.0265 (11)	0.0252 (10)	0.0263 (10)	−0.0050 (8)	−0.0014 (8)	−0.0033 (8)
C19'	0.0258 (10)	0.0194 (10)	0.0243 (10)	−0.0001 (8)	−0.0046 (8)	−0.0029 (8)
O20'	0.0205 (7)	0.0184 (7)	0.0248 (7)	−0.0039 (5)	−0.0021 (5)	0.0033 (5)
C21'	0.0204 (10)	0.0216 (10)	0.0260 (10)	−0.0064 (8)	−0.0079 (8)	0.0007 (8)
O22'	0.0226 (7)	0.0148 (6)	0.0303 (7)	−0.0043 (5)	−0.0021 (6)	0.0009 (5)
O23'	0.0298 (8)	0.0242 (7)	0.0345 (8)	−0.0115 (6)	−0.0059 (6)	0.0067 (6)
O24'	0.0294 (7)	0.0154 (6)	0.0235 (7)	0.0007 (5)	−0.0069 (5)	−0.0016 (5)
C25'	0.0204 (10)	0.0235 (10)	0.0255 (11)	−0.0023 (8)	−0.0077 (8)	0.0011 (8)
O26'	0.0626 (10)	0.0264 (8)	0.0268 (8)	−0.0135 (7)	−0.0178 (7)	0.0013 (6)
C27'	0.0184 (10)	0.0195 (10)	0.0301 (11)	−0.0006 (7)	−0.0075 (8)	−0.0021 (8)
C28'	0.0420 (13)	0.0270 (11)	0.0291 (11)	−0.0067 (9)	−0.0059 (9)	−0.0012 (9)
C29'	0.0523 (14)	0.0217 (11)	0.0457 (14)	−0.0112 (10)	−0.0027 (11)	0.0000 (10)
C30'	0.0337 (12)	0.0260 (11)	0.0440 (13)	−0.0073 (9)	−0.0034 (10)	−0.0121 (10)
C31'	0.0191 (10)	0.0304 (11)	0.0315 (11)	−0.0022 (8)	−0.0030 (8)	−0.0115 (9)
C32'	0.0141 (9)	0.0242 (10)	0.0305 (11)	−0.0008 (7)	−0.0048 (8)	−0.0029 (8)
O33'	0.0259 (7)	0.0194 (7)	0.0340 (8)	−0.0078 (5)	−0.0057 (6)	−0.0095 (6)
O34'	0.0230 (7)	0.0230 (7)	0.0334 (7)	−0.0082 (5)	−0.0084 (6)	−0.0017 (6)
C35'	0.0419 (13)	0.0394 (13)	0.0365 (12)	−0.0245 (10)	−0.0065 (10)	−0.0009 (10)
O36'	0.0221 (8)	0.0521 (10)	0.0644 (11)	−0.0103 (7)	−0.0081 (7)	−0.0220 (8)
C37'	0.0500 (15)	0.0592 (16)	0.0602 (17)	−0.0112 (12)	−0.0312 (13)	−0.0112 (13)
C1P	0.040 (3)	0.054 (4)	0.045 (3)	−0.006 (3)	−0.007 (3)	−0.007 (3)
C2P	0.047 (5)	0.029 (3)	0.026 (3)	−0.002 (4)	−0.006 (4)	−0.005 (2)
C3P	0.057 (9)	0.022 (5)	0.021 (3)	0.000 (6)	0.008 (6)	−0.008 (3)
C4P	0.054 (7)	0.042 (4)	0.031 (3)	−0.003 (5)	0.002 (4)	−0.004 (3)
C5P	0.047 (6)	0.051 (5)	0.040 (3)	−0.011 (5)	−0.003 (5)	0.008 (3)

Geometric parameters (Å, º) top

C1—O22	1.466 (2)	C3'—C8'	1.555 (2)
C1—C14	1.519 (2)	C3'—H3'	1.0
C1—C15	1.536 (2)	C4'—O34'	1.438 (2)
C1—C2	1.551 (2)	C4'—C5'	1.516 (2)
C2—O20	1.455 (2)	C4'—H4'	1.0
C2—C3	1.538 (2)	C5'—C6'	1.521 (3)
C2—H2	1.0	C5'—H5'A	0.99
C3—C4	1.531 (2)	C5'—H5'B	0.99
C3—C8	1.560 (2)	C6'—C7'	1.506 (3)
C3—H3	1.0	C6'—H6'A	0.99
C4—O34	1.445 (2)	C6'—H6'B	0.99
C4—C5	1.517 (2)	C7'—O24'	1.456 (2)
C4—H4	1.0	C7'—C8'	1.542 (2)
C5—C6	1.527 (2)	C7'—H7'	1.0
C5—H5A	0.99	C8'—C19'	1.534 (2)
C5—H5B	0.99	C8'—C9'	1.552 (2)
C6—C7	1.509 (2)	C9'—C10'	1.552 (2)
C6—H6A	0.99	C9'—H9'A	0.99
C6—H6B	0.99	C9'—H9'B	0.99
C7—O24	1.470 (2)	C10'—O33'	1.440 (2)
C7—C8	1.544 (2)	C10'—C11'	1.565 (2)
C7—H7	1.0	C10'—H10'	1.0
C8—C19	1.527 (2)	C11'—C12'	1.520 (2)
C8—C9	1.550 (2)	C11'—C15'	1.557 (2)
C9—C10	1.544 (2)	C11'—H11'	1.0
C9—H9B	0.99	C12'—C13'	1.326 (2)
C9—H9A	0.99	C12'—C18'	1.496 (2)
C10—O33	1.429 (2)	C13'—C14'	1.495 (2)
C10—C11	1.567 (2)	C13'—H13'	0.95
C10—H10	1.0	C14'—H14D	0.99
C11—C12	1.520 (2)	C14'—H14E	0.99
C11—C15	1.559 (2)	C15'—C16'	1.532 (2)
C11—H11	1.0	C15'—C17'	1.539 (2)
C12—C13	1.327 (2)	C16'—H16D	0.98
C12—C18	1.502 (2)	C16'—H16E	0.98
C13—C14	1.496 (2)	C16'—H16F	0.98
C13—H13	0.95	C17'—H17D	0.98
C14—H14A	0.99	C17'—H17E	0.98
C14—H14B	0.99	C17'—H17F	0.98
C15—C16	1.535 (2)	C18'—H18D	0.98
C15—C17	1.538 (2)	C18'—H18E	0.98
C16—H16A	0.98	C18'—H18F	0.98
C16—H16B	0.98	C19'—H19D	0.98
C16—H16C	0.98	C19'—H19E	0.98
C17—H17B	0.98	C19'—H19F	0.98
C17—H17C	0.98	O20'—C21'	1.331 (2)
C17—H17A	0.98	C21'—O23'	1.192 (2)
C18—H18A	0.98	C21'—O22'	1.342 (2)
C18—H18B	0.98	O24'—C25'	1.339 (2)
C18—H18C	0.98	C25'—O26'	1.201 (2)
C19—H19C	0.98	C25'—C27'	1.489 (3)
C19—H19A	0.98	C27'—C28'	1.383 (3)
C19—H19B	0.98	C27'—C32'	1.390 (3)
O20—C21	1.330 (2)	C28'—C29'	1.385 (3)
C21—O23	1.193 (2)	C28'—H28'	0.95
C21—O22	1.343 (2)	C29'—C30'	1.375 (3)
O24—C25	1.340 (2)	C29'—H29'	0.95
C25—O26	1.207 (2)	C30'—C31'	1.374 (3)
C25—C27	1.487 (2)	C30'—H30'	0.95
C27—C32	1.391 (2)	C31'—C32'	1.383 (3)
C27—C28	1.391 (2)	C31'—H31'	0.95
C28—C29	1.379 (3)	C32'—H32'	0.95
C28—H28	0.95	O33'—H33'	0.84
C29—C30	1.379 (3)	O34'—C35'	1.397 (2)
C29—H29	0.95	C35'—O36'	1.390 (3)
C30—C31	1.380 (3)	C35'—H35D	0.99
C30—H30	0.95	C35'—H35F	0.99
C31—C32	1.386 (3)	O36'—C37'	1.408 (3)
C31—H31	0.95	C37'—H37D	0.98
C32—H32	0.95	C37'—H37E	0.98
O33—H33	0.84	C37'—H37F	0.98
O34—C35	1.401 (2)	C1P—C2P	1.512 (7)
C35—O36	1.388 (2)	C1P—H1PA	0.98
C35—H35A	0.99	C1P—H1PB	0.98
C35—H35B	0.99	C1P—H1PC	0.98
O36—C37	1.419 (2)	C2P—C3P	1.527 (12)
C37—H37B	0.98	C2P—H2PA	0.99
C37—H37C	0.98	C2P—H2PB	0.99
C37—H37A	0.98	C3P—C4P	1.513 (9)
C1'—O22'	1.468 (2)	C3P—H3PA	0.99
C1'—C14'	1.517 (2)	C3P—H3PB	0.99
C1'—C15'	1.539 (2)	C4P—C5P	1.519 (13)
C1'—C2'	1.548 (2)	C4P—H4PA	0.99
C2'—O20'	1.455 (2)	C4P—H4PB	0.99
C2'—C3'	1.539 (2)	C5P—H5PA	0.98
C2'—H2'	1.0	C5P—H5PB	0.98
C3'—C4'	1.531 (2)	C5P—H5PC	0.98

O22—C1—C14	106.92 (13)	C4'—C3'—H3'	106.8
O22—C1—C15	109.83 (13)	C2'—C3'—H3'	106.8
C14—C1—C15	110.95 (14)	C8'—C3'—H3'	106.8
O22—C1—C2	101.66 (13)	O34'—C4'—C5'	111.30 (14)
C14—C1—C2	115.83 (14)	O34'—C4'—C3'	105.04 (13)
C15—C1—C2	111.06 (13)	C5'—C4'—C3'	111.67 (15)
O20—C2—C3	111.66 (13)	O34'—C4'—H4'	109.6
O20—C2—C1	104.22 (12)	C5'—C4'—H4'	109.6
C3—C2—C1	119.74 (14)	C3'—C4'—H4'	109.6
O20—C2—H2	106.8	C4'—C5'—C6'	110.44 (15)
C3—C2—H2	106.8	C4'—C5'—H5'A	109.6
C1—C2—H2	106.8	C6'—C5'—H5'A	109.6
C4—C3—C2	112.38 (14)	C4'—C5'—H5'B	109.6
C4—C3—C8	114.30 (13)	C6'—C5'—H5'B	109.6
C2—C3—C8	109.19 (13)	H5'A—C5'—H5'B	108.1
C4—C3—H3	106.8	C7'—C6'—C5'	108.79 (15)
C2—C3—H3	106.8	C7'—C6'—H6'A	109.9
C8—C3—H3	106.8	C5'—C6'—H6'A	109.9
O34—C4—C5	110.55 (14)	C7'—C6'—H6'B	109.9
O34—C4—C3	105.85 (13)	C5'—C6'—H6'B	109.9
C5—C4—C3	111.33 (14)	H6'A—C6'—H6'B	108.3
O34—C4—H4	109.7	O24'—C7'—C6'	109.24 (14)
C5—C4—H4	109.7	O24'—C7'—C8'	107.71 (13)
C3—C4—H4	109.7	C6'—C7'—C8'	114.27 (15)
C4—C5—C6	110.58 (14)	O24'—C7'—H7'	108.5
C4—C5—H5A	109.5	C6'—C7'—H7'	108.5
C6—C5—H5A	109.5	C8'—C7'—H7'	108.5
C4—C5—H5B	109.5	C19'—C8'—C7'	109.93 (14)
C6—C5—H5B	109.5	C19'—C8'—C9'	111.03 (14)
H5A—C5—H5B	108.1	C7'—C8'—C9'	105.96 (14)
C7—C6—C5	108.84 (14)	C19'—C8'—C3'	112.37 (14)
C7—C6—H6A	109.9	C7'—C8'—C3'	106.79 (13)
C5—C6—H6A	109.9	C9'—C8'—C3'	110.48 (14)
C7—C6—H6B	109.9	C8'—C9'—C10'	124.69 (14)
C5—C6—H6B	109.9	C8'—C9'—H9'A	106.2
H6A—C6—H6B	108.3	C10'—C9'—H9'A	106.2
O24—C7—C6	110.10 (13)	C8'—C9'—H9'B	106.2
O24—C7—C8	106.75 (13)	C10'—C9'—H9'B	106.2
C6—C7—C8	114.54 (14)	H9'A—C9'—H9'B	106.3
O24—C7—H7	108.4	O33'—C10'—C9'	106.31 (13)
C6—C7—H7	108.4	O33'—C10'—C11'	102.98 (13)
C8—C7—H7	108.4	C9'—C10'—C11'	119.59 (14)
C19—C8—C7	109.82 (14)	O33'—C10'—H10'	109.1
C19—C8—C9	111.08 (14)	C9'—C10'—H10'	109.1
C7—C8—C9	105.73 (13)	C11'—C10'—H10'	109.1
C19—C8—C3	112.58 (14)	C12'—C11'—C15'	110.97 (14)
C7—C8—C3	106.92 (13)	C12'—C11'—C10'	112.90 (14)
C9—C8—C3	110.40 (13)	C15'—C11'—C10'	119.20 (14)
C10—C9—C8	122.76 (14)	C12'—C11'—H11'	104.0
C10—C9—H9B	106.6	C15'—C11'—H11'	104.0
C8—C9—H9B	106.6	C10'—C11'—H11'	104.0
C10—C9—H9A	106.6	C13'—C12'—C18'	122.25 (16)
C8—C9—H9A	106.6	C13'—C12'—C11'	121.39 (16)
H9B—C9—H9A	106.6	C18'—C12'—C11'	116.29 (15)
O33—C10—C9	108.12 (14)	C12'—C13'—C14'	125.10 (16)
O33—C10—C11	103.00 (13)	C12'—C13'—H13'	117.4
C9—C10—C11	118.56 (14)	C14'—C13'—H13'	117.4
O33—C10—H10	108.9	C13'—C14'—C1'	111.79 (14)
C9—C10—H10	108.9	C13'—C14'—H14D	109.3
C11—C10—H10	108.9	C1'—C14'—H14D	109.3
C12—C11—C15	110.87 (14)	C13'—C14'—H14E	109.3
C12—C11—C10	113.25 (14)	C1'—C14'—H14E	109.3
C15—C11—C10	118.18 (14)	H14D—C14'—H14E	107.9
C12—C11—H11	104.3	C16'—C15'—C1'	112.57 (14)
C15—C11—H11	104.3	C16'—C15'—C17'	105.41 (14)
C10—C11—H11	104.3	C1'—C15'—C17'	111.34 (14)
C13—C12—C18	121.45 (16)	C16'—C15'—C11'	113.16 (14)
C13—C12—C11	121.67 (16)	C1'—C15'—C11'	106.73 (13)
C18—C12—C11	116.82 (15)	C17'—C15'—C11'	107.59 (14)
C12—C13—C14	124.68 (16)	C15'—C16'—H16D	109.5
C12—C13—H13	117.7	C15'—C16'—H16E	109.5
C14—C13—H13	117.7	H16D—C16'—H16E	109.5
C13—C14—C1	111.73 (14)	C15'—C16'—H16F	109.5
C13—C14—H14A	109.3	H16D—C16'—H16F	109.5
C1—C14—H14A	109.3	H16E—C16'—H16F	109.5
C13—C14—H14B	109.3	C15'—C17'—H17D	109.5
C1—C14—H14B	109.3	C15'—C17'—H17E	109.5
H14A—C14—H14B	107.9	H17D—C17'—H17E	109.5
C16—C15—C1	112.74 (14)	C15'—C17'—H17F	109.5
C16—C15—C17	105.90 (14)	H17D—C17'—H17F	109.5
C1—C15—C17	110.91 (14)	H17E—C17'—H17F	109.5
C16—C15—C11	112.53 (14)	C12'—C18'—H18D	109.5
C1—C15—C11	106.34 (13)	C12'—C18'—H18E	109.5
C17—C15—C11	108.40 (14)	H18D—C18'—H18E	109.5
C15—C16—H16A	109.5	C12'—C18'—H18F	109.5
C15—C16—H16B	109.5	H18D—C18'—H18F	109.5
H16A—C16—H16B	109.5	H18E—C18'—H18F	109.5
C15—C16—H16C	109.5	C8'—C19'—H19D	109.5
H16A—C16—H16C	109.5	C8'—C19'—H19E	109.5
H16B—C16—H16C	109.5	H19D—C19'—H19E	109.5
C15—C17—H17B	109.5	C8'—C19'—H19F	109.5
C15—C17—H17C	109.5	H19D—C19'—H19F	109.5
H17B—C17—H17C	109.5	H19E—C19'—H19F	109.5
C15—C17—H17A	109.5	C21'—O20'—C2'	110.28 (13)
H17B—C17—H17A	109.5	O23'—C21'—O20'	124.57 (17)
H17C—C17—H17A	109.5	O23'—C21'—O22'	123.78 (16)
C12—C18—H18A	109.5	O20'—C21'—O22'	111.64 (15)
C12—C18—H18B	109.5	C21'—O22'—C1'	111.54 (13)
H18A—C18—H18B	109.5	C25'—O24'—C7'	117.38 (13)
C12—C18—H18C	109.5	O26'—C25'—O24'	123.87 (17)
H18A—C18—H18C	109.5	O26'—C25'—C27'	124.10 (17)
H18B—C18—H18C	109.5	O24'—C25'—C27'	112.03 (15)
C8—C19—H19C	109.5	C28'—C27'—C32'	119.59 (17)
C8—C19—H19A	109.5	C28'—C27'—C25'	117.84 (17)
H19C—C19—H19A	109.5	C32'—C27'—C25'	122.57 (16)
C8—C19—H19B	109.5	C27'—C28'—C29'	120.05 (19)
H19C—C19—H19B	109.5	C27'—C28'—H28'	120.0
H19A—C19—H19B	109.5	C29'—C28'—H28'	120.0
C21—O20—C2	110.60 (13)	C30'—C29'—C28'	120.18 (19)
O23—C21—O20	124.81 (17)	C30'—C29'—H29'	119.9
O23—C21—O22	123.59 (16)	C28'—C29'—H29'	119.9
O20—C21—O22	111.60 (15)	C31'—C30'—C29'	120.00 (19)
C21—O22—C1	111.40 (13)	C31'—C30'—H30'	120.0
C25—O24—C7	116.45 (13)	C29'—C30'—H30'	120.0
O26—C25—O24	123.80 (16)	C30'—C31'—C32'	120.44 (18)
O26—C25—C27	123.31 (16)	C30'—C31'—H31'	119.8
O24—C25—C27	112.90 (15)	C32'—C31'—H31'	119.8
C32—C27—C28	119.41 (16)	C31'—C32'—C27'	119.73 (17)
C32—C27—C25	122.92 (16)	C31'—C32'—H32'	120.1
C28—C27—C25	117.67 (16)	C27'—C32'—H32'	120.1
C29—C28—C27	120.35 (17)	C10'—O33'—H33'	109.5
C29—C28—H28	119.8	C35'—O34'—C4'	115.53 (14)
C27—C28—H28	119.8	O36'—C35'—O34'	114.07 (17)
C28—C29—C30	120.01 (18)	O36'—C35'—H35D	108.7
C28—C29—H29	120.0	O34'—C35'—H35D	108.7
C30—C29—H29	120.0	O36'—C35'—H35F	108.7
C29—C30—C31	120.18 (17)	O34'—C35'—H35F	108.7
C29—C30—H30	119.9	H35D—C35'—H35F	107.6
C31—C30—H30	119.9	C35'—O36'—C37'	112.82 (17)
C30—C31—C32	120.23 (17)	O36'—C37'—H37D	109.5
C30—C31—H31	119.9	O36'—C37'—H37E	109.5
C32—C31—H31	119.9	H37D—C37'—H37E	109.5
C31—C32—C27	119.80 (17)	O36'—C37'—H37F	109.5
C31—C32—H32	120.1	H37D—C37'—H37F	109.5
C27—C32—H32	120.1	H37E—C37'—H37F	109.5
C10—O33—H33	109.5	C2P—C1P—H1PA	109.5
C35—O34—C4	115.66 (13)	C2P—C1P—H1PB	109.5
O36—C35—O34	114.13 (14)	H1PA—C1P—H1PB	109.5
O36—C35—H35A	108.7	C2P—C1P—H1PC	109.5
O34—C35—H35A	108.7	H1PA—C1P—H1PC	109.5
O36—C35—H35B	108.7	H1PB—C1P—H1PC	109.5
O34—C35—H35B	108.7	C1P—C2P—C3P	113.0 (6)
H35A—C35—H35B	107.6	C1P—C2P—H2PA	109.0
C35—O36—C37	112.85 (15)	C3P—C2P—H2PA	109.0
O36—C37—H37B	109.5	C1P—C2P—H2PB	109.0
O36—C37—H37C	109.5	C3P—C2P—H2PB	109.0
H37B—C37—H37C	109.5	H2PA—C2P—H2PB	107.8
O36—C37—H37A	109.5	C4P—C3P—C2P	113.9 (5)
H37B—C37—H37A	109.5	C4P—C3P—H3PA	108.8
H37C—C37—H37A	109.5	C2P—C3P—H3PA	108.8
O22'—C1'—C14'	107.45 (13)	C4P—C3P—H3PB	108.8
O22'—C1'—C15'	109.95 (13)	C2P—C3P—H3PB	108.8
C14'—C1'—C15'	111.00 (14)	H3PA—C3P—H3PB	107.7
O22'—C1'—C2'	101.43 (13)	C3P—C4P—C5P	113.0 (6)
C14'—C1'—C2'	116.01 (14)	C3P—C4P—H4PA	109.0
C15'—C1'—C2'	110.45 (13)	C5P—C4P—H4PA	109.0
O20'—C2'—C3'	111.74 (13)	C3P—C4P—H4PB	109.0
O20'—C2'—C1'	104.56 (13)	C5P—C4P—H4PB	109.0
C3'—C2'—C1'	119.08 (14)	H4PA—C4P—H4PB	107.8
O20'—C2'—H2'	106.9	C4P—C5P—H5PA	109.5
C3'—C2'—H2'	106.9	C4P—C5P—H5PB	109.5
C1'—C2'—H2'	106.9	H5PA—C5P—H5PB	109.5
C4'—C3'—C2'	112.31 (14)	C4P—C5P—H5PC	109.5
C4'—C3'—C8'	115.02 (14)	H5PA—C5P—H5PC	109.5
C2'—C3'—C8'	108.62 (13)	H5PB—C5P—H5PC	109.5

O22—C1—C2—O20	6.62 (15)	C14'—C1'—C2'—O20'	−109.03 (15)
C14—C1—C2—O20	−108.85 (15)	C15'—C1'—C2'—O20'	123.57 (14)
C15—C1—C2—O20	123.41 (14)	O22'—C1'—C2'—C3'	132.64 (15)
O22—C1—C2—C3	132.30 (14)	C14'—C1'—C2'—C3'	16.6 (2)
C14—C1—C2—C3	16.8 (2)	C15'—C1'—C2'—C3'	−110.81 (17)
C15—C1—C2—C3	−110.91 (17)	O20'—C2'—C3'—C4'	13.44 (19)
O20—C2—C3—C4	11.23 (19)	C1'—C2'—C3'—C4'	−108.67 (17)
C1—C2—C3—C4	−110.86 (16)	O20'—C2'—C3'—C8'	−114.93 (15)
O20—C2—C3—C8	−116.69 (14)	C1'—C2'—C3'—C8'	122.97 (16)
C1—C2—C3—C8	121.21 (16)	C2'—C3'—C4'—O34'	62.79 (17)
C2—C3—C4—O34	61.23 (17)	C8'—C3'—C4'—O34'	−172.30 (13)
C8—C3—C4—O34	−173.60 (13)	C2'—C3'—C4'—C5'	−176.44 (15)
C2—C3—C4—C5	−178.60 (14)	C8'—C3'—C4'—C5'	−51.5 (2)
C8—C3—C4—C5	−53.42 (19)	O34'—C4'—C5'—C6'	172.16 (14)
O34—C4—C5—C6	173.67 (14)	C3'—C4'—C5'—C6'	55.1 (2)
C3—C4—C5—C6	56.31 (19)	C4'—C5'—C6'—C7'	−59.6 (2)
C4—C5—C6—C7	−59.01 (19)	C5'—C6'—C7'—O24'	−177.36 (14)
C5—C6—C7—O24	−179.24 (13)	C5'—C6'—C7'—C8'	61.9 (2)
C5—C6—C7—C8	60.47 (19)	O24'—C7'—C8'—C19'	−54.39 (18)
O24—C7—C8—C19	−54.43 (17)	C6'—C7'—C8'—C19'	67.17 (19)
C6—C7—C8—C19	67.71 (18)	O24'—C7'—C8'—C9'	65.65 (16)
O24—C7—C8—C9	65.48 (16)	C6'—C7'—C8'—C9'	−172.78 (14)
C6—C7—C8—C9	−172.38 (14)	O24'—C7'—C8'—C3'	−176.55 (13)
O24—C7—C8—C3	−176.86 (13)	C6'—C7'—C8'—C3'	−54.99 (19)
C6—C7—C8—C3	−54.72 (18)	C4'—C3'—C8'—C19'	−71.54 (18)
C4—C3—C8—C19	−70.39 (18)	C2'—C3'—C8'—C19'	55.28 (18)
C2—C3—C8—C19	56.45 (18)	C4'—C3'—C8'—C7'	49.07 (19)
C4—C3—C8—C7	50.29 (18)	C2'—C3'—C8'—C7'	175.89 (14)
C2—C3—C8—C7	177.14 (13)	C4'—C3'—C8'—C9'	163.86 (14)
C4—C3—C8—C9	164.85 (14)	C2'—C3'—C8'—C9'	−69.33 (17)
C2—C3—C8—C9	−68.31 (17)	C19'—C8'—C9'—C10'	−66.3 (2)
C19—C8—C9—C10	−64.8 (2)	C7'—C8'—C9'—C10'	174.41 (15)
C7—C8—C9—C10	176.12 (14)	C3'—C8'—C9'—C10'	59.1 (2)
C3—C8—C9—C10	60.8 (2)	C8'—C9'—C10'—O33'	161.84 (15)
C8—C9—C10—O33	155.68 (15)	C8'—C9'—C10'—C11'	−82.4 (2)
C8—C9—C10—C11	−87.7 (2)	O33'—C10'—C11'—C12'	89.06 (16)
O33—C10—C11—C12	95.01 (16)	C9'—C10'—C11'—C12'	−28.5 (2)
C9—C10—C11—C12	−24.3 (2)	O33'—C10'—C11'—C15'	−138.00 (15)
O33—C10—C11—C15	−132.92 (15)	C9'—C10'—C11'—C15'	104.46 (18)
C9—C10—C11—C15	107.80 (18)	C15'—C11'—C12'—C13'	−21.8 (2)
C15—C11—C12—C13	−22.0 (2)	C10'—C11'—C12'—C13'	115.02 (18)
C10—C11—C12—C13	113.52 (18)	C15'—C11'—C12'—C18'	155.27 (15)
C15—C11—C12—C18	155.30 (15)	C10'—C11'—C12'—C18'	−67.92 (19)
C10—C11—C12—C18	−69.16 (19)	C18'—C12'—C13'—C14'	−177.07 (16)
C18—C12—C13—C14	−177.24 (16)	C11'—C12'—C13'—C14'	−0.2 (3)
C11—C12—C13—C14	0.0 (3)	C12'—C13'—C14'—C1'	−10.8 (2)
C12—C13—C14—C1	−11.1 (2)	O22'—C1'—C14'—C13'	164.26 (14)
O22—C1—C14—C13	164.41 (13)	C15'—C1'—C14'—C13'	44.01 (19)
C15—C1—C14—C13	44.66 (19)	C2'—C1'—C14'—C13'	−83.12 (18)
C2—C1—C14—C13	−83.13 (18)	O22'—C1'—C15'—C16'	51.20 (18)
O22—C1—C15—C16	52.28 (18)	C14'—C1'—C15'—C16'	169.96 (14)
C14—C1—C15—C16	170.27 (14)	C2'—C1'—C15'—C16'	−59.92 (18)
C2—C1—C15—C16	−59.38 (18)	O22'—C1'—C15'—C17'	−66.92 (18)
O22—C1—C15—C17	−66.29 (17)	C14'—C1'—C15'—C17'	51.83 (18)
C14—C1—C15—C17	51.70 (18)	C2'—C1'—C15'—C17'	−178.04 (14)
C2—C1—C15—C17	−177.95 (14)	O22'—C1'—C15'—C11'	175.93 (13)
O22—C1—C15—C11	176.05 (12)	C14'—C1'—C15'—C11'	−65.31 (17)
C14—C1—C15—C11	−65.96 (17)	C2'—C1'—C15'—C11'	64.81 (17)
C2—C1—C15—C11	64.39 (17)	C12'—C11'—C15'—C16'	176.85 (14)
C12—C11—C15—C16	176.78 (14)	C10'—C11'—C15'—C16'	43.1 (2)
C10—C11—C15—C16	43.7 (2)	C12'—C11'—C15'—C1'	52.47 (17)
C12—C11—C15—C1	52.87 (17)	C10'—C11'—C15'—C1'	−81.28 (18)
C10—C11—C15—C1	−80.24 (17)	C12'—C11'—C15'—C17'	−67.12 (17)
C12—C11—C15—C17	−66.44 (17)	C10'—C11'—C15'—C17'	159.12 (14)
C10—C11—C15—C17	160.45 (14)	C3'—C2'—O20'—C21'	−136.82 (14)
C3—C2—O20—C21	−135.34 (14)	C1'—C2'—O20'—C21'	−6.71 (17)
C1—C2—O20—C21	−4.71 (17)	C2'—O20'—C21'—O23'	−176.50 (16)
C2—O20—C21—O23	−179.45 (17)	C2'—O20'—C21'—O22'	3.45 (19)
C2—O20—C21—O22	0.49 (18)	O23'—C21'—O22'—C1'	−178.39 (16)
O23—C21—O22—C1	−175.69 (16)	O20'—C21'—O22'—C1'	1.65 (19)
O20—C21—O22—C1	4.37 (19)	C14'—C1'—O22'—C21'	116.66 (15)
C14—C1—O22—C21	115.03 (15)	C15'—C1'—O22'—C21'	−122.43 (15)
C15—C1—O22—C21	−124.50 (14)	C2'—C1'—O22'—C21'	−5.52 (17)
C2—C1—O22—C21	−6.83 (17)	C6'—C7'—O24'—C25'	91.63 (18)
C6—C7—O24—C25	88.35 (17)	C8'—C7'—O24'—C25'	−143.73 (15)
C8—C7—O24—C25	−146.75 (14)	C7'—O24'—C25'—O26'	2.1 (3)
C7—O24—C25—O26	−5.8 (2)	C7'—O24'—C25'—C27'	−178.74 (14)
C7—O24—C25—C27	173.98 (13)	O26'—C25'—C27'—C28'	9.8 (3)
O26—C25—C27—C32	−171.09 (17)	O24'—C25'—C27'—C28'	−169.38 (16)
O24—C25—C27—C32	9.1 (2)	O26'—C25'—C27'—C32'	−170.79 (18)
O26—C25—C27—C28	9.3 (3)	O24'—C25'—C27'—C32'	10.0 (2)
O24—C25—C27—C28	−170.50 (15)	C32'—C27'—C28'—C29'	−0.9 (3)
C32—C27—C28—C29	0.5 (3)	C25'—C27'—C28'—C29'	178.55 (18)
C25—C27—C28—C29	−179.89 (16)	C27'—C28'—C29'—C30'	0.7 (3)
C27—C28—C29—C30	0.4 (3)	C28'—C29'—C30'—C31'	0.3 (3)
C28—C29—C30—C31	−0.5 (3)	C29'—C30'—C31'—C32'	−1.2 (3)
C29—C30—C31—C32	−0.4 (3)	C30'—C31'—C32'—C27'	1.0 (3)
C30—C31—C32—C27	1.2 (3)	C28'—C27'—C32'—C31'	0.0 (3)
C28—C27—C32—C31	−1.3 (3)	C25'—C27'—C32'—C31'	−179.37 (16)
C25—C27—C32—C31	179.11 (16)	C5'—C4'—O34'—C35'	83.68 (19)
C5—C4—O34—C35	99.01 (17)	C3'—C4'—O34'—C35'	−155.31 (15)
C3—C4—O34—C35	−140.30 (14)	C4'—O34'—C35'—O36'	−79.7 (2)
C4—O34—C35—O36	−79.12 (18)	O34'—C35'—O36'—C37'	−66.5 (2)
O34—C35—O36—C37	−71.1 (2)	C1P—C2P—C3P—C4P	175.9 (6)
O22'—C1'—C2'—O20'	7.02 (15)	C2P—C3P—C4P—C5P	179.1 (10)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C27–C32 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O34	0.99	2.47	3.320 (2)	143
C14′—H14D···O34′	0.99	2.36	3.221 (2)	145
O33—H33···O22′ⁱ	0.84	2.05	2.8563 (17)	160
O33′—H33′···O22ⁱⁱ	0.84	2.05	2.8839 (16)	169
C7—H7···O26ⁱⁱⁱ	1.00	2.28	3.236 (2)	159
C4′—H4′···O36^iv	1.00	2.40	3.311 (2)	151
C17′—H17F···O33ⁱ	0.98	2.48	3.431 (2)	164
C30′—H30′···O23′^v	0.95	2.53	3.453 (2)	163
C3P—H3PB···O33	0.99	2.49	3.369 (9)	149
C4P—H4PA···O33ⁱ	0.99	2.41	3.291 (12)	148
C16′—H16D···Cg1ⁱ	0.98	2.85	3.5315 (19)	127

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+2, −z+2; (iv) x+1, y, z−1; (v) x, y−1, z.

(B) (±)-(1SR,5SR,6SR,7SR,10SR,11SR,13SR,14SR)-13-Hydroxy-7-methoxymethoxy-11,15,18,18-tetramethyl-3-oxo-2,4-dioxatetracyclo[12.3.1.0^1,5.0^6,11]octadec-15-en-10-yl benzoate top

Crystal data top

C₂₉H₃₈O₈	D_x = 1.338 Mg m⁻³
M_r = 514.59	Melting point: 489.2 K
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.3612 (6) Å	Cell parameters from 4716 reflections
b = 19.6336 (15) Å	θ = 2.4–23.9°
c = 14.1965 (9) Å	µ = 0.10 mm⁻¹
β = 101.762 (2)°	T = 90 K
V = 2554.4 (3) Å³	Prism, colorless
Z = 4	0.23 × 0.23 × 0.14 mm
F(000) = 1104

Data collection top

Bruker D8 Venture diffractometer	4480 independent reflections
Radiation source: fine-focus sealed tube	3212 reflections with I > 2σ(I)
Multilayered confocal mirror monochromator	R_int = 0.058
Detector resolution: 8.333 pixels mm^-1	θ_max = 25.0°, θ_min = 2.5°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −23→21
T_min = 0.98, T_max = 0.99	l = −16→16
23252 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.054P)² + 1.0752P] where P = (F_o² + 2F_c²)/3
4480 reflections	(Δ/σ)_max = 0.001
340 parameters	Δρ_max = 0.51 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Special details top

Experimental. M.p. 488.2–489.2 K (not corrected); IR (film) 3483, 2940, 1799, 1717, 1274, 1099, 1042, 773 cm^-1; ¹H NMR (500 MHz, CDCl₃, at 333 K) δ (p.p.m.) 8.02 (d, J = 7.7 Hz, 2H), 7.58 (t, J = 7.5 Hz, 1H), 7.46 (t, J = 7.7 Hz, 2H), 5.50 (s, 1H), 4.92 (d, J = 4.3 Hz, 1H), 4.91 (dd J = 11.7, 4.9 Hz, 1H), 4.80 (d, J = 6.9 Hz, 1H), 4.64 (d, J = 6.9 Hz, 1H), 4.31 (d, J = 10.9 Hz, 1H), 3.68 (ddd, J = 10.9, 10.6, 4.9 Hz, 1H), 3.39 (s, 3H), 3.19 (d, J = 16.9 Hz, 1H), 2.42 (dd, J = 10.9, 4.3 Hz, 1H), 2.33 (s, 1H), 2.33–2.27 (m, 1H), 2.26 (d, J = 16.9 Hz, 1H), 2.02 (dd, J = 16.0, 10.9 Hz, 1H), 1.95–1.87 (m, 1H), 1.88 (s, 3H), 1.82 (dddd, J = 13.6, 13.6, 13.6, 4.6 Hz, 1H), 1.72 (d, J = 16.0 Hz, 1H), 1.49–1.40 (m, 1H), 1.46 (s, 1H), 1.41 (s, 3H), 1.20 (s, 3H), 1.18 (s, 3H); ¹³C NMR (125 MHz, CDCl₃, at 333 K) δ (p.p.m.) 166.3 (C), 154.4 (C), 136.3 (C), 133.4 (CH), 130.4 (C), 129.8 (CH), 128.7 (CH), 122.3 (CH), 97.7 (CH₂), 88.5 (C), 79.5 (CH), 75.2 (CH), 74.3 (CH), 70.3 (CH), 60.0 (CH), 56.1 (CH₃), 44.8 (CH₂), 44.2 (CH), 42.0 (C), 39.0 (C), 32.0 (CH₂), 30.7 (CH₂), 28.6 (CH₃), 25.6 (CH₂), 22.9 (CH₃), 20.8 (CH₃), 16.1 (CH₃); LRMS (EI) m/z 514 (M⁺, 3%), 483 (1), 469 (1), 453 (1), 409 (2), 393 (6), 348 (1), 332 (2), 121 (78), 105 (100), 77 (59); HRMS (EI) m/z calcd for C₂₉H₃₈O₈⁺ [M]⁺ 514.2567, found 514.2560.

Problematic one reflection with |I(obs)-I(calc)|/σW(I) greater than 10 (-1 0 1) has been omitted in the final refinement.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.7169 (2)	0.18654 (10)	0.68618 (13)	0.0143 (4)
C2	0.6544 (2)	0.17259 (10)	0.77738 (14)	0.0136 (4)
H2	0.6782	0.2123	0.8195	0.016*
C3	0.7047 (2)	0.10935 (10)	0.83870 (13)	0.0131 (4)
H3	0.7884	0.0905	0.8158	0.016*
C4	0.5888 (2)	0.05350 (10)	0.82692 (14)	0.0157 (5)
H4	0.5005	0.0711	0.8454	0.019*
C5	0.6453 (2)	−0.00784 (10)	0.88896 (14)	0.0181 (5)
H5A	0.7279	−0.0275	0.8671	0.022*
H5B	0.5695	−0.0422	0.8827	0.022*
C6	0.6915 (2)	0.01330 (11)	0.99391 (14)	0.0192 (5)
H6A	0.6073	0.0301	1.0169	0.023*
H6B	0.7295	−0.026	1.0325	0.023*
C7	0.8069 (2)	0.06816 (10)	1.00523 (13)	0.0155 (4)
H7	0.8952	0.0491	0.9884	0.019*
C8	0.7615 (2)	0.13268 (10)	0.94372 (14)	0.0135 (4)
C9	0.9051 (2)	0.17425 (10)	0.94939 (14)	0.0164 (5)
H9B	0.9393	0.1848	1.017	0.02*
H9A	0.9752	0.1424	0.9326	0.02*
C10	0.9238 (2)	0.24112 (10)	0.89436 (14)	0.0166 (5)
H10	1.0181	0.259	0.9281	0.02*
C11	0.9370 (2)	0.24049 (10)	0.78491 (14)	0.0172 (5)
H11	1.0036	0.2782	0.7801	0.021*
C12	1.0208 (2)	0.17776 (11)	0.76571 (14)	0.0174 (5)
C13	0.9588 (2)	0.12865 (10)	0.70699 (14)	0.0167 (5)
H13	1.0156	0.0911	0.6989	0.02*
C14	0.8037 (2)	0.12964 (10)	0.65293 (14)	0.0154 (4)
H14A	0.7581	0.0864	0.6617	0.018*
H14B	0.8021	0.1351	0.5848	0.018*
C15	0.8037 (2)	0.25338 (10)	0.69973 (14)	0.0154 (5)
C16	0.7084 (2)	0.31455 (10)	0.71360 (14)	0.0191 (5)
H16B	0.6447	0.3255	0.6535	0.029*
H16C	0.7695	0.353	0.7355	0.029*
H16A	0.6512	0.3035	0.7604	0.029*
C17	0.8650 (2)	0.27030 (11)	0.60997 (15)	0.0209 (5)
H17A	0.9377	0.2373	0.6029	0.031*
H17B	0.908	0.3149	0.6168	0.031*
H17C	0.7874	0.2693	0.5541	0.031*
C18	1.1796 (2)	0.17407 (12)	0.81421 (16)	0.0242 (5)
H18B	1.2193	0.1311	0.7998	0.036*
H18C	1.1887	0.1783	0.8825	0.036*
H18A	1.232	0.2104	0.7912	0.036*
C19	0.6461 (2)	0.17224 (11)	0.98432 (14)	0.0176 (5)
H19C	0.6149	0.2111	0.9444	0.026*
H19A	0.6873	0.1871	1.0485	0.026*
H19B	0.5639	0.1432	0.9854	0.026*
O20	0.49732 (15)	0.17278 (7)	0.74303 (9)	0.0176 (3)
C21	0.4646 (2)	0.18489 (10)	0.64927 (15)	0.0178 (5)
O22	0.58327 (14)	0.19463 (7)	0.61213 (9)	0.0170 (3)
O23	0.34190 (16)	0.18696 (8)	0.60281 (10)	0.0247 (4)
O24	0.84116 (15)	0.09012 (7)	1.10583 (9)	0.0168 (3)
C25	0.9381 (2)	0.05274 (10)	1.16731 (14)	0.0154 (4)
O26	1.00007 (16)	0.00371 (7)	1.14311 (10)	0.0237 (4)
C27	0.9612 (2)	0.07873 (10)	1.26731 (14)	0.0153 (4)
C28	0.8754 (2)	0.13006 (11)	1.29508 (14)	0.0194 (5)
H28	0.7979	0.1484	1.2508	0.023*
C29	0.9062 (2)	0.15358 (12)	1.38896 (15)	0.0252 (5)
H29	0.8491	0.1878	1.4077	0.03*
C30	1.0214 (2)	0.12650 (11)	1.45491 (15)	0.0231 (5)
H30	1.0417	0.1428	1.5178	0.028*
C31	1.1063 (2)	0.07552 (11)	1.42812 (15)	0.0227 (5)
H31	1.1832	0.0571	1.4728	0.027*
C32	1.0765 (2)	0.05194 (10)	1.33430 (14)	0.0187 (5)
H32	1.1342	0.0179	1.316	0.022*
O33	0.82270 (15)	0.29278 (7)	0.90665 (10)	0.0200 (3)
H33	0.8271	0.2993	0.9642	0.03*
O34	0.55698 (14)	0.03544 (7)	0.72690 (9)	0.0188 (3)
C35	0.4129 (2)	0.01081 (12)	0.69395 (15)	0.0232 (5)
H35A	0.3957	−0.0281	0.7322	0.028*
H35B	0.343	0.046	0.7007	0.028*
O36	0.39527 (17)	−0.00779 (8)	0.59939 (11)	0.0289 (4)
C37	0.4715 (3)	−0.06965 (12)	0.58715 (17)	0.0315 (6)
H37C	0.5739	−0.0637	0.6126	0.047*
H37A	0.4566	−0.0805	0.5199	0.047*
H37B	0.4349	−0.1061	0.6207	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0139 (11)	0.0176 (11)	0.0096 (10)	0.0000 (9)	−0.0017 (8)	0.0003 (8)
C2	0.0092 (10)	0.0182 (11)	0.0126 (10)	0.0005 (8)	0.0003 (8)	−0.0006 (8)
C3	0.0116 (11)	0.0156 (10)	0.0126 (11)	0.0014 (8)	0.0039 (8)	−0.0003 (8)
C4	0.0154 (11)	0.0203 (11)	0.0114 (11)	−0.0014 (9)	0.0026 (9)	−0.0038 (8)
C5	0.0187 (11)	0.0147 (11)	0.0216 (12)	−0.0040 (9)	0.0060 (9)	−0.0018 (9)
C6	0.0218 (12)	0.0190 (11)	0.0174 (11)	−0.0008 (9)	0.0052 (9)	0.0041 (9)
C7	0.0192 (11)	0.0184 (11)	0.0091 (10)	0.0018 (9)	0.0030 (9)	−0.0003 (8)
C8	0.0132 (11)	0.0142 (11)	0.0129 (11)	0.0003 (8)	0.0025 (8)	−0.0007 (8)
C9	0.0167 (11)	0.0174 (11)	0.0133 (11)	0.0010 (9)	−0.0009 (9)	−0.0013 (8)
C10	0.0154 (11)	0.0171 (11)	0.0162 (11)	−0.0002 (9)	0.0010 (9)	−0.0025 (8)
C11	0.0153 (11)	0.0185 (11)	0.0179 (11)	−0.0039 (9)	0.0039 (9)	−0.0010 (9)
C12	0.0160 (11)	0.0205 (11)	0.0170 (11)	−0.0006 (9)	0.0067 (9)	−0.0004 (9)
C13	0.0176 (11)	0.0178 (11)	0.0162 (11)	0.0030 (9)	0.0071 (9)	0.0015 (9)
C14	0.0200 (11)	0.0156 (11)	0.0118 (11)	0.0001 (9)	0.0059 (9)	−0.0001 (8)
C15	0.0170 (11)	0.0153 (11)	0.0141 (11)	0.0000 (9)	0.0040 (9)	0.0005 (8)
C16	0.0217 (12)	0.0188 (11)	0.0152 (11)	0.0028 (9)	0.0003 (9)	0.0027 (8)
C17	0.0248 (12)	0.0187 (11)	0.0207 (12)	−0.0029 (9)	0.0079 (10)	0.0009 (9)
C18	0.0184 (12)	0.0282 (13)	0.0263 (13)	0.0004 (10)	0.0052 (10)	−0.0049 (10)
C19	0.0199 (12)	0.0188 (11)	0.0140 (11)	0.0016 (9)	0.0032 (9)	0.0003 (8)
O20	0.0137 (8)	0.0265 (8)	0.0119 (8)	0.0036 (6)	0.0011 (6)	0.0032 (6)
C21	0.0195 (13)	0.0173 (11)	0.0167 (12)	−0.0003 (9)	0.0041 (10)	0.0018 (9)
O22	0.0152 (8)	0.0225 (8)	0.0124 (7)	0.0000 (6)	0.0007 (6)	0.0024 (6)
O23	0.0157 (9)	0.0375 (10)	0.0189 (8)	0.0007 (7)	−0.0014 (7)	0.0077 (7)
O24	0.0197 (8)	0.0197 (8)	0.0101 (7)	0.0043 (6)	0.0011 (6)	0.0004 (6)
C25	0.0159 (11)	0.0149 (11)	0.0154 (11)	−0.0005 (9)	0.0033 (9)	0.0034 (8)
O26	0.0295 (9)	0.0225 (8)	0.0179 (8)	0.0102 (7)	0.0023 (7)	−0.0004 (6)
C27	0.0173 (11)	0.0139 (10)	0.0152 (11)	−0.0024 (9)	0.0042 (9)	0.0024 (8)
C28	0.0175 (12)	0.0242 (12)	0.0158 (12)	0.0022 (9)	0.0021 (9)	0.0018 (9)
C29	0.0241 (13)	0.0317 (13)	0.0203 (13)	0.0071 (10)	0.0060 (10)	−0.0027 (10)
C30	0.0268 (13)	0.0293 (13)	0.0135 (11)	−0.0049 (10)	0.0045 (10)	−0.0027 (9)
C31	0.0227 (12)	0.0235 (12)	0.0195 (12)	−0.0011 (10)	−0.0010 (10)	0.0050 (9)
C32	0.0221 (12)	0.0155 (11)	0.0181 (11)	0.0006 (9)	0.0031 (9)	0.0010 (9)
O33	0.0251 (8)	0.0187 (8)	0.0162 (8)	0.0041 (6)	0.0046 (7)	−0.0028 (6)
O34	0.0166 (8)	0.0248 (8)	0.0140 (8)	−0.0046 (6)	0.0004 (6)	−0.0050 (6)
C35	0.0183 (12)	0.0304 (13)	0.0196 (12)	−0.0042 (10)	0.0007 (9)	−0.0070 (9)
O36	0.0293 (9)	0.0288 (9)	0.0249 (9)	0.0012 (7)	−0.0031 (7)	−0.0049 (7)
C37	0.0328 (14)	0.0255 (13)	0.0355 (14)	−0.0026 (11)	0.0056 (11)	−0.0103 (11)

Geometric parameters (Å, º) top

C1—O22	1.469 (2)	C15—C17	1.536 (3)
C1—C14	1.512 (3)	C16—H16B	0.96
C1—C15	1.535 (3)	C16—H16C	0.96
C1—C2	1.550 (3)	C16—H16A	0.96
C2—O20	1.452 (2)	C17—H17A	0.96
C2—C3	1.534 (3)	C17—H17B	0.96
C2—H2	0.98	C17—H17C	0.96
C3—C4	1.528 (3)	C18—H18B	0.96
C3—C8	1.547 (3)	C18—H18C	0.96
C3—H3	0.98	C18—H18A	0.96
C4—O34	1.435 (2)	C19—H19C	0.96
C4—C5	1.522 (3)	C19—H19A	0.96
C4—H4	0.98	C19—H19B	0.96
C5—C6	1.522 (3)	O20—C21	1.325 (2)
C5—H5A	0.97	C21—O23	1.203 (2)
C5—H5B	0.97	C21—O22	1.337 (2)
C6—C7	1.511 (3)	O24—C25	1.342 (2)
C6—H6A	0.97	C25—O26	1.210 (2)
C6—H6B	0.97	C25—C27	1.482 (3)
C7—O24	1.464 (2)	C27—C32	1.389 (3)
C7—C8	1.548 (3)	C27—C28	1.395 (3)
C7—H7	0.98	C28—C29	1.384 (3)
C8—C19	1.535 (3)	C28—H28	0.93
C8—C9	1.561 (3)	C29—C30	1.382 (3)
C9—C10	1.556 (3)	C29—H29	0.93
C9—H9B	0.97	C30—C31	1.379 (3)
C9—H9A	0.97	C30—H30	0.93
C10—O33	1.422 (2)	C31—C32	1.384 (3)
C10—C11	1.584 (3)	C31—H31	0.93
C10—H10	0.98	C32—H32	0.93
C11—C12	1.515 (3)	O33—H33	0.82
C11—C15	1.571 (3)	O34—C35	1.419 (2)
C11—H11	0.98	C35—O36	1.368 (2)
C12—C13	1.328 (3)	C35—H35A	0.97
C12—C18	1.507 (3)	C35—H35B	0.97
C13—C14	1.498 (3)	O36—C37	1.437 (3)
C13—H13	0.93	C37—H37C	0.96
C14—H14A	0.97	C37—H37A	0.96
C14—H14B	0.97	C37—H37B	0.96
C15—C16	1.533 (3)

O22—C1—C14	106.84 (15)	C13—C14—H14B	109.2
O22—C1—C15	110.43 (15)	C1—C14—H14B	109.2
C14—C1—C15	111.48 (16)	H14A—C14—H14B	107.9
O22—C1—C2	101.84 (15)	C16—C15—C1	112.24 (16)
C14—C1—C2	116.66 (16)	C16—C15—C17	105.23 (16)
C15—C1—C2	109.08 (15)	C1—C15—C17	111.01 (16)
O20—C2—C3	111.43 (15)	C16—C15—C11	114.78 (16)
O20—C2—C1	104.36 (14)	C1—C15—C11	106.00 (16)
C3—C2—C1	119.49 (16)	C17—C15—C11	107.56 (16)
O20—C2—H2	107.0	C15—C16—H16B	109.5
C3—C2—H2	107.0	C15—C16—H16C	109.5
C1—C2—H2	107.0	H16B—C16—H16C	109.5
C4—C3—C2	112.93 (16)	C15—C16—H16A	109.5
C4—C3—C8	114.52 (15)	H16B—C16—H16A	109.5
C2—C3—C8	108.22 (16)	H16C—C16—H16A	109.5
C4—C3—H3	106.9	C15—C17—H17A	109.5
C2—C3—H3	106.9	C15—C17—H17B	109.5
C8—C3—H3	106.9	H17A—C17—H17B	109.5
O34—C4—C5	110.78 (16)	C15—C17—H17C	109.5
O34—C4—C3	106.57 (15)	H17A—C17—H17C	109.5
C5—C4—C3	110.44 (16)	H17B—C17—H17C	109.5
O34—C4—H4	109.7	C12—C18—H18B	109.5
C5—C4—H4	109.7	C12—C18—H18C	109.5
C3—C4—H4	109.7	H18B—C18—H18C	109.5
C4—C5—C6	110.28 (17)	C12—C18—H18A	109.5
C4—C5—H5A	109.6	H18B—C18—H18A	109.5
C6—C5—H5A	109.6	H18C—C18—H18A	109.5
C4—C5—H5B	109.6	C8—C19—H19C	109.5
C6—C5—H5B	109.6	C8—C19—H19A	109.5
H5A—C5—H5B	108.1	H19C—C19—H19A	109.5
C7—C6—C5	110.65 (16)	C8—C19—H19B	109.5
C7—C6—H6A	109.5	H19C—C19—H19B	109.5
C5—C6—H6A	109.5	H19A—C19—H19B	109.5
C7—C6—H6B	109.5	C21—O20—C2	110.43 (15)
C5—C6—H6B	109.5	O23—C21—O20	123.82 (19)
H6A—C6—H6B	108.1	O23—C21—O22	123.79 (18)
O24—C7—C6	108.86 (15)	O20—C21—O22	112.39 (18)
O24—C7—C8	106.83 (15)	C21—O22—C1	110.93 (15)
C6—C7—C8	114.51 (17)	C25—O24—C7	117.26 (15)
O24—C7—H7	108.8	O26—C25—O24	123.40 (18)
C6—C7—H7	108.8	O26—C25—C27	124.13 (18)
C8—C7—H7	108.8	O24—C25—C27	112.46 (17)
C19—C8—C3	112.46 (16)	C32—C27—C28	119.50 (18)
C19—C8—C7	109.62 (16)	C32—C27—C25	117.84 (18)
C3—C8—C7	107.59 (15)	C28—C27—C25	122.63 (18)
C19—C8—C9	112.39 (16)	C29—C28—C27	119.61 (19)
C3—C8—C9	109.13 (15)	C29—C28—H28	120.2
C7—C8—C9	105.30 (16)	C27—C28—H28	120.2
C10—C9—C8	126.80 (17)	C30—C29—C28	120.3 (2)
C10—C9—H9B	105.6	C30—C29—H29	119.8
C8—C9—H9B	105.6	C28—C29—H29	119.8
C10—C9—H9A	105.6	C31—C30—C29	120.4 (2)
C8—C9—H9A	105.6	C31—C30—H30	119.8
H9B—C9—H9A	106.1	C29—C30—H30	119.8
O33—C10—C9	113.25 (16)	C30—C31—C32	119.6 (2)
O33—C10—C11	108.23 (15)	C30—C31—H31	120.2
C9—C10—C11	121.68 (16)	C32—C31—H31	120.2
O33—C10—H10	103.9	C31—C32—C27	120.6 (2)
C9—C10—H10	103.9	C31—C32—H32	119.7
C11—C10—H10	103.9	C27—C32—H32	119.7
C12—C11—C15	110.59 (16)	C10—O33—H33	109.5
C12—C11—C10	109.26 (16)	C35—O34—C4	113.70 (14)
C15—C11—C10	123.08 (16)	O36—C35—O34	109.31 (16)
C12—C11—H11	104.0	O36—C35—H35A	109.8
C15—C11—H11	104.0	O34—C35—H35A	109.8
C10—C11—H11	104.0	O36—C35—H35B	109.8
C13—C12—C18	121.05 (19)	O34—C35—H35B	109.8
C13—C12—C11	121.81 (19)	H35A—C35—H35B	108.3
C18—C12—C11	117.12 (18)	C35—O36—C37	112.38 (17)
C12—C13—C14	124.47 (19)	O36—C37—H37C	109.5
C12—C13—H13	117.8	O36—C37—H37A	109.5
C14—C13—H13	117.8	H37C—C37—H37A	109.5
C13—C14—C1	112.09 (16)	O36—C37—H37B	109.5
C13—C14—H14A	109.2	H37C—C37—H37B	109.5
C1—C14—H14A	109.2	H37A—C37—H37B	109.5

O22—C1—C2—O20	1.49 (18)	O22—C1—C14—C13	164.37 (15)
C14—C1—C2—O20	−114.39 (18)	C15—C1—C14—C13	43.6 (2)
C15—C1—C2—O20	118.23 (16)	C2—C1—C14—C13	−82.6 (2)
O22—C1—C2—C3	126.81 (17)	O22—C1—C15—C16	50.0 (2)
C14—C1—C2—C3	10.9 (3)	C14—C1—C15—C16	168.56 (16)
C15—C1—C2—C3	−116.45 (19)	C2—C1—C15—C16	−61.2 (2)
O20—C2—C3—C4	15.6 (2)	O22—C1—C15—C17	−67.5 (2)
C1—C2—C3—C4	−106.25 (19)	C14—C1—C15—C17	51.1 (2)
O20—C2—C3—C8	−112.22 (17)	C2—C1—C15—C17	−178.64 (16)
C1—C2—C3—C8	125.90 (18)	O22—C1—C15—C11	176.00 (14)
C2—C3—C4—O34	59.3 (2)	C14—C1—C15—C11	−65.40 (19)
C8—C3—C4—O34	−176.20 (15)	C2—C1—C15—C11	64.86 (19)
C2—C3—C4—C5	179.71 (16)	C12—C11—C15—C16	178.07 (16)
C8—C3—C4—C5	−55.8 (2)	C10—C11—C15—C16	46.4 (3)
O34—C4—C5—C6	174.93 (15)	C12—C11—C15—C1	53.6 (2)
C3—C4—C5—C6	57.1 (2)	C10—C11—C15—C1	−78.1 (2)
C4—C5—C6—C7	−57.8 (2)	C12—C11—C15—C17	−65.2 (2)
C5—C6—C7—O24	176.31 (15)	C10—C11—C15—C17	163.09 (17)
C5—C6—C7—C8	56.8 (2)	C3—C2—O20—C21	−130.71 (17)
C4—C3—C8—C19	−69.6 (2)	C1—C2—O20—C21	−0.4 (2)
C2—C3—C8—C19	57.3 (2)	C2—O20—C21—O23	179.11 (19)
C4—C3—C8—C7	51.2 (2)	C2—O20—C21—O22	−1.0 (2)
C2—C3—C8—C7	178.13 (15)	O23—C21—O22—C1	−178.01 (19)
C4—C3—C8—C9	164.96 (16)	O20—C21—O22—C1	2.1 (2)
C2—C3—C8—C9	−68.11 (19)	C14—C1—O22—C21	120.70 (17)
O24—C7—C8—C19	−49.8 (2)	C15—C1—O22—C21	−117.90 (17)
C6—C7—C8—C19	70.8 (2)	C2—C1—O22—C21	−2.14 (19)
O24—C7—C8—C3	−172.37 (14)	C6—C7—O24—C25	83.5 (2)
C6—C7—C8—C3	−51.8 (2)	C8—C7—O24—C25	−152.31 (16)
O24—C7—C8—C9	71.32 (18)	C7—O24—C25—O26	2.0 (3)
C6—C7—C8—C9	−168.07 (16)	C7—O24—C25—C27	−178.54 (15)
C19—C8—C9—C10	−65.5 (2)	O26—C25—C27—C32	10.3 (3)
C3—C8—C9—C10	60.0 (2)	O24—C25—C27—C32	−169.09 (17)
C7—C8—C9—C10	175.21 (18)	O26—C25—C27—C28	−171.9 (2)
C8—C9—C10—O33	52.8 (3)	O24—C25—C27—C28	8.7 (3)
C8—C9—C10—C11	−78.9 (3)	C32—C27—C28—C29	0.0 (3)
O33—C10—C11—C12	−169.30 (16)	C25—C27—C28—C29	−177.76 (19)
C9—C10—C11—C12	−35.5 (2)	C27—C28—C29—C30	0.1 (3)
O33—C10—C11—C15	−37.1 (2)	C28—C29—C30—C31	−0.4 (3)
C9—C10—C11—C15	96.7 (2)	C29—C30—C31—C32	0.6 (3)
C15—C11—C12—C13	−23.7 (3)	C30—C31—C32—C27	−0.6 (3)
C10—C11—C12—C13	114.8 (2)	C28—C27—C32—C31	0.3 (3)
C15—C11—C12—C18	154.73 (17)	C25—C27—C32—C31	178.12 (18)
C10—C11—C12—C18	−66.8 (2)	C5—C4—O34—C35	88.2 (2)
C18—C12—C13—C14	−177.43 (18)	C3—C4—O34—C35	−151.61 (17)
C11—C12—C13—C14	1.0 (3)	C4—O34—C35—O36	−177.35 (16)
C12—C13—C14—C1	−10.5 (3)	O34—C35—O36—C37	72.7 (2)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C27–C32 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O33	0.98	2.27	3.200 (2)	157
C14—H14A···O34	0.97	2.47	3.293 (2)	142
O33—H33···O23ⁱ	0.82	1.96	2.7823 (19)	179
C7—H7···O26ⁱⁱ	0.98	2.50	3.353 (2)	145
C16—H16A···Cg2ⁱⁱⁱ	0.98	2.93	3.594 (2)	128

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+2, −y, −z+2; (iii) x−3/2, −y−1/2, z−3/2.

(C) (±)-(1SR,5SR,6SR,7SR,10SR,11SR,14SR)-7-Methoxymethoxy-11,15,18,18-tetramethyl-3,13-dioxo-2,4-dioxatetracyclo[12.3.1.0^1,5.0^6,11]octadec-15-en-10-yl benzoate top

Crystal data top

C₂₉H₃₆O₈	D_x = 1.357 Mg m⁻³
M_r = 512.59	Melting point: 512.2 K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.2416 (8) Å	Cell parameters from 6186 reflections
b = 13.1779 (8) Å	θ = 2.8–24.9°
c = 15.2428 (8) Å	µ = 0.10 mm⁻¹
β = 109.387 (2)°	T = 90 K
V = 2509.0 (3) Å³	Plate, colorless
Z = 4	0.22 × 0.14 × 0.09 mm
F(000) = 1096

Data collection top

Bruker D8 Venture diffractometer	4395 independent reflections
Radiation source: fine-focus sealed tube	3050 reflections with I > 2σ(I)
Multilayered confocal mirror monochromator	R_int = 0.063
Detector resolution: 8.333 pixels mm^-1	θ_max = 25.0°, θ_min = 2.4°
φ and ω scans	h = −15→14
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −15→15
T_min = 0.92, T_max = 0.99	l = −16→18
22512 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H-atom parameters constrained
S = 0.96	w = 1/[σ²(F_o²) + (0.0391P)² + 2.2049P] where P = (F_o² + 2F_c²)/3
4395 reflections	(Δ/σ)_max = 0.001
339 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Special details top

Experimental. M.p. 510.7–512.2 K (not corrected); IR (film) 2934, 1804, 1718, 1689, 1668, 1272, 1230, 1108, 1058, 732, 713 cm^-1; ¹H NMR (500 MHz, CDCl₃) δ (p.p.m.) 8.05–8.98 (m, 2H), 7.62–7.56 (m, 1H), 7.49–7.43 (m, 2H), 5.73 (bs, 1H), 4.79 (d, J = 6.9 Hz, 1H), 4.76 (dd, J = 11.0, 4.0 Hz, 1H), 4.60 (d, J = 6.9 Hz, 1H), 4.22 (d, J = 3.4 Hz, 1H), 3.62 (ddd, J = 10.6, 10.3, 5.2 Hz, 1H), 3.37 (s, 3H), 3.00 (bd, J = 17.0 Hz, 1H), 2.61 (d, J = 10.9 Hz, 1H), 2.51 (d, J = 17.0 Hz, 1H), 2.47 (s, 1H), 2.42–2.35 (m, 1H), 2.33 (dd, J = 10.6, 3.4 Hz, 1H), 2.13 (d, J = 10.9 Hz, 1H), 1.95–1.88 (m, 1H), 1.71 (s, 3H), 1.71–1.52 (m, 2H), 1.27 (s, 3H), 1.17 (s, 3H), 1.16 (s, 3H); ¹³C NMR (125 MHz, CDCl₃) δ (p.p.m.) 211.2 (C), 165.9 (C), 153.7 (C), 135.8 (C), 133.5 (CH), 129.8 (C), 129.7 (CH), 128.7 (CH), 122.6 (CH), 97.8 (CH₂), 87.0 (C), 79.3 (CH), 79.0 (CH), 74.7 (CH), 65.7 (CH), 56.0 (CH₃), 51.2 (CH₂), 48.0 (CH), 47.1 (C), 44.1 (C), 31.9 (CH₂), 31.2 (CH₂), 25.1 (CH₃), 24.6 (CH₃), 24.6 (CH₂), 19.3 (CH₃), 12.3 (CH₃); LRMS (EI) m/z 512 (M⁺, 5%), 346 (9), 302 (7), 121 (28), 105 (100), 77 (55); HRMS (EI) m/z calcd for C₂₉H₃₆O₈⁺ [M]⁺ 512.2410, found 514.2408.

Problematic two reflections with |I(obs)-I(calc)|/σW(I) greater than 10 (1 1 0 and 11 4 3) have been omitted in the final refinement.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.81842 (17)	0.32712 (17)	0.49210 (14)	0.0156 (5)
C2	0.83265 (18)	0.43504 (17)	0.53612 (14)	0.0157 (5)
H2	0.8939	0.4312	0.5959	0.019*
C3	0.73832 (17)	0.48566 (16)	0.55835 (14)	0.0141 (5)
H3	0.6787	0.435	0.5422	0.017*
C4	0.69530 (17)	0.58009 (17)	0.49830 (14)	0.0151 (5)
H4	0.7551	0.629	0.5048	0.018*
C5	0.60735 (18)	0.63170 (17)	0.52421 (14)	0.0186 (5)
H5A	0.543	0.5879	0.5055	0.022*
H5B	0.5884	0.6962	0.4894	0.022*
C6	0.63941 (18)	0.65384 (17)	0.62826 (14)	0.0191 (5)
H6A	0.699	0.7034	0.6466	0.023*
H6B	0.578	0.6834	0.6427	0.023*
C7	0.67390 (18)	0.55614 (17)	0.68165 (13)	0.0152 (5)
H7	0.6122	0.5078	0.6641	0.018*
C8	0.77033 (17)	0.50500 (16)	0.66456 (14)	0.0144 (5)
C9	0.78727 (18)	0.40213 (17)	0.71791 (14)	0.0170 (5)
H9B	0.8022	0.4176	0.7846	0.02*
H9A	0.7185	0.3648	0.6963	0.02*
C10	0.87422 (19)	0.33035 (17)	0.71100 (14)	0.0176 (5)
C11	0.84777 (17)	0.23989 (17)	0.64233 (14)	0.0169 (5)
H11	0.8853	0.1799	0.6791	0.02*
C12	0.72983 (18)	0.21357 (17)	0.60918 (15)	0.0170 (5)
C13	0.66633 (18)	0.23789 (17)	0.52443 (15)	0.0179 (5)
H13	0.5922	0.2228	0.5084	0.021*
C14	0.70379 (17)	0.28774 (17)	0.45229 (14)	0.0175 (5)
H14A	0.6555	0.3451	0.4243	0.021*
H14B	0.6994	0.2383	0.4023	0.021*
C15	0.89166 (17)	0.24989 (17)	0.55936 (14)	0.0177 (5)
C16	1.00975 (18)	0.28215 (18)	0.59015 (16)	0.0209 (5)
H16A	1.0171	0.3507	0.6165	0.031*
H16B	1.0346	0.2816	0.5363	0.031*
H16C	1.0528	0.2347	0.6373	0.031*
C17	0.88509 (19)	0.14530 (17)	0.51289 (16)	0.0221 (6)
H17C	0.9039	0.152	0.4562	0.033*
H17A	0.8121	0.1188	0.497	0.033*
H17B	0.9351	0.0985	0.5559	0.033*
C18	0.69208 (19)	0.15857 (18)	0.67848 (15)	0.0222 (6)
H18B	0.6144	0.1488	0.6528	0.033*
H18C	0.7096	0.1985	0.7358	0.033*
H18A	0.7275	0.0924	0.6922	0.033*
C19	0.87058 (18)	0.57156 (17)	0.70192 (15)	0.0186 (5)
H19A	0.8809	0.5905	0.7665	0.028*
H19B	0.8617	0.633	0.6639	0.028*
H19C	0.9332	0.5337	0.6992	0.028*
O20	0.86805 (11)	0.49630 (11)	0.47260 (9)	0.0165 (4)
C21	0.87791 (17)	0.43902 (18)	0.40303 (15)	0.0169 (5)
O22	0.85523 (12)	0.34137 (12)	0.41269 (10)	0.0187 (4)
O23	0.90357 (12)	0.47131 (12)	0.34036 (10)	0.0224 (4)
O24	0.70651 (11)	0.57550 (11)	0.78110 (9)	0.0170 (4)
C25	0.63110 (18)	0.57567 (16)	0.82216 (15)	0.0146 (5)
O26	0.53686 (12)	0.56418 (12)	0.78106 (10)	0.0203 (4)
C27	0.67949 (18)	0.58868 (16)	0.92408 (14)	0.0150 (5)
C28	0.61586 (19)	0.57355 (17)	0.97941 (15)	0.0212 (5)
H28	0.5422	0.5574	0.9515	0.025*
C29	0.6597 (2)	0.58201 (18)	1.07519 (15)	0.0237 (6)
H29	0.6161	0.5712	1.1128	0.028*
C30	0.7661 (2)	0.60592 (18)	1.11608 (16)	0.0255 (6)
H30	0.796	0.6109	1.1818	0.031*
C31	0.8296 (2)	0.62271 (18)	1.06145 (16)	0.0250 (6)
H31	0.9028	0.6403	1.0896	0.03*
C32	0.78646 (19)	0.61393 (18)	0.96603 (15)	0.0215 (5)
H32	0.8304	0.6253	0.9288	0.026*
O33	0.96560 (13)	0.34029 (12)	0.76362 (10)	0.0236 (4)
O34	0.65380 (12)	0.54447 (11)	0.40409 (9)	0.0182 (4)
C35	0.67590 (19)	0.60542 (18)	0.33721 (15)	0.0214 (6)
H35A	0.7532	0.6218	0.3592	0.026*
H35B	0.6603	0.566	0.2789	0.026*
O36	0.61766 (12)	0.69614 (11)	0.31770 (10)	0.0200 (4)
C37	0.50654 (18)	0.68122 (18)	0.27053 (16)	0.0243 (6)
H37B	0.4746	0.647	0.312	0.036*
H37C	0.4967	0.6393	0.2152	0.036*
H37A	0.4717	0.7471	0.2518	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0189 (13)	0.0175 (13)	0.0133 (11)	0.0015 (10)	0.0092 (10)	−0.0016 (9)
C2	0.0189 (13)	0.0148 (13)	0.0149 (11)	−0.0009 (10)	0.0079 (10)	0.0026 (9)
C3	0.0149 (12)	0.0126 (12)	0.0152 (11)	−0.0002 (10)	0.0056 (9)	−0.0016 (9)
C4	0.0166 (12)	0.0147 (13)	0.0130 (11)	−0.0004 (10)	0.0037 (10)	−0.0012 (9)
C5	0.0216 (13)	0.0163 (13)	0.0183 (11)	0.0057 (10)	0.0071 (10)	0.0028 (10)
C6	0.0228 (13)	0.0159 (13)	0.0212 (12)	0.0041 (10)	0.0109 (10)	−0.0006 (10)
C7	0.0192 (12)	0.0160 (13)	0.0112 (11)	−0.0035 (10)	0.0061 (10)	−0.0036 (9)
C8	0.0154 (12)	0.0156 (13)	0.0129 (11)	−0.0015 (10)	0.0058 (9)	−0.0010 (9)
C9	0.0199 (13)	0.0170 (13)	0.0150 (11)	0.0001 (10)	0.0070 (10)	−0.0003 (9)
C10	0.0209 (14)	0.0182 (13)	0.0137 (11)	−0.0007 (11)	0.0055 (11)	0.0052 (10)
C11	0.0187 (13)	0.0134 (13)	0.0178 (11)	0.0010 (10)	0.0049 (10)	0.0024 (9)
C12	0.0197 (13)	0.0128 (13)	0.0201 (12)	−0.0010 (10)	0.0089 (10)	−0.0034 (10)
C13	0.0180 (13)	0.0132 (13)	0.0226 (12)	−0.0012 (10)	0.0070 (10)	−0.0040 (10)
C14	0.0192 (13)	0.0151 (13)	0.0154 (11)	0.0009 (10)	0.0021 (10)	−0.0013 (9)
C15	0.0191 (13)	0.0144 (13)	0.0197 (12)	0.0023 (10)	0.0066 (10)	−0.0003 (10)
C16	0.0204 (13)	0.0179 (14)	0.0257 (12)	0.0051 (10)	0.0094 (10)	0.0026 (10)
C17	0.0260 (14)	0.0167 (14)	0.0252 (12)	0.0024 (11)	0.0106 (11)	−0.0014 (10)
C18	0.0242 (14)	0.0209 (14)	0.0229 (12)	−0.0011 (11)	0.0096 (11)	−0.0002 (10)
C19	0.0205 (13)	0.0180 (13)	0.0181 (11)	−0.0001 (10)	0.0074 (10)	−0.0028 (10)
O20	0.0199 (9)	0.0152 (9)	0.0177 (8)	−0.0015 (7)	0.0109 (7)	−0.0013 (7)
C21	0.0127 (12)	0.0184 (14)	0.0175 (12)	0.0024 (10)	0.0022 (10)	−0.0007 (10)
O22	0.0258 (9)	0.0165 (9)	0.0177 (8)	−0.0001 (7)	0.0122 (7)	−0.0014 (7)
O23	0.0254 (9)	0.0267 (10)	0.0201 (8)	−0.0039 (8)	0.0139 (7)	0.0004 (7)
O24	0.0194 (9)	0.0194 (9)	0.0139 (7)	−0.0010 (7)	0.0079 (7)	−0.0032 (6)
C25	0.0171 (13)	0.0079 (12)	0.0222 (12)	0.0014 (10)	0.0109 (11)	0.0004 (9)
O26	0.0175 (10)	0.0225 (10)	0.0211 (8)	−0.0019 (7)	0.0066 (7)	−0.0029 (7)
C27	0.0199 (13)	0.0108 (12)	0.0146 (11)	0.0022 (10)	0.0061 (10)	0.0003 (9)
C28	0.0256 (14)	0.0157 (13)	0.0235 (12)	0.0022 (11)	0.0098 (11)	0.0009 (10)
C29	0.0333 (16)	0.0241 (15)	0.0172 (12)	0.0041 (12)	0.0129 (12)	0.0027 (10)
C30	0.0390 (16)	0.0196 (14)	0.0150 (12)	0.0049 (12)	0.0052 (12)	0.0012 (10)
C31	0.0263 (14)	0.0230 (15)	0.0220 (13)	−0.0033 (11)	0.0029 (11)	−0.0035 (10)
C32	0.0243 (14)	0.0214 (14)	0.0212 (12)	−0.0008 (11)	0.0106 (11)	−0.0026 (10)
O33	0.0205 (10)	0.0264 (10)	0.0200 (8)	0.0017 (8)	0.0016 (8)	−0.0005 (7)
O34	0.0248 (9)	0.0179 (9)	0.0124 (7)	0.0017 (7)	0.0068 (7)	0.0018 (6)
C35	0.0241 (14)	0.0254 (15)	0.0162 (12)	0.0067 (11)	0.0087 (11)	0.0051 (10)
O36	0.0203 (9)	0.0162 (9)	0.0221 (8)	−0.0005 (7)	0.0052 (7)	0.0047 (7)
C37	0.0200 (14)	0.0243 (15)	0.0275 (13)	0.0014 (11)	0.0065 (11)	0.0056 (11)

Geometric parameters (Å, º) top

C1—O22	1.459 (2)	C15—C17	1.539 (3)
C1—C14	1.526 (3)	C16—H16A	0.98
C1—C15	1.539 (3)	C16—H16B	0.98
C1—C2	1.557 (3)	C16—H16C	0.98
C2—O20	1.453 (2)	C17—H17C	0.98
C2—C3	1.550 (3)	C17—H17A	0.98
C2—H2	1.0	C17—H17B	0.98
C3—C4	1.538 (3)	C18—H18B	0.98
C3—C8	1.552 (3)	C18—H18C	0.98
C3—H3	1.0	C18—H18A	0.98
C4—O34	1.435 (2)	C19—H19A	0.98
C4—C5	1.510 (3)	C19—H19B	0.98
C4—H4	1.0	C19—H19C	0.98
C5—C6	1.528 (3)	O20—C21	1.343 (3)
C5—H5A	0.99	C21—O23	1.193 (2)
C5—H5B	0.99	C21—O22	1.341 (3)
C6—C7	1.510 (3)	O24—C25	1.343 (2)
C6—H6A	0.99	C25—O26	1.206 (3)
C6—H6B	0.99	C25—C27	1.481 (3)
C7—O24	1.454 (2)	C27—C32	1.387 (3)
C7—C8	1.540 (3)	C27—C28	1.390 (3)
C7—H7	1.0	C28—C29	1.385 (3)
C8—C19	1.534 (3)	C28—H28	0.95
C8—C9	1.558 (3)	C29—C30	1.374 (3)
C9—C10	1.521 (3)	C29—H29	0.95
C9—H9B	0.99	C30—C31	1.384 (3)
C9—H9A	0.99	C30—H30	0.95
C10—O33	1.217 (3)	C31—C32	1.380 (3)
C10—C11	1.548 (3)	C31—H31	0.95
C11—C12	1.514 (3)	C32—H32	0.95
C11—C15	1.563 (3)	O34—C35	1.403 (3)
C11—H11	1.0	C35—O36	1.400 (3)
C12—C13	1.326 (3)	C35—H35A	0.99
C12—C18	1.497 (3)	C35—H35B	0.99
C13—C14	1.500 (3)	O36—C37	1.421 (3)
C13—H13	0.95	C37—H37B	0.98
C14—H14A	0.99	C37—H37C	0.98
C14—H14B	0.99	C37—H37A	0.98
C15—C16	1.536 (3)

O22—C1—C14	106.01 (16)	C1—C14—H14B	109.1
O22—C1—C15	109.12 (17)	H14A—C14—H14B	107.8
C14—C1—C15	111.33 (18)	C16—C15—C1	111.91 (18)
O22—C1—C2	102.36 (16)	C16—C15—C17	106.55 (18)
C14—C1—C2	116.36 (18)	C1—C15—C17	111.04 (18)
C15—C1—C2	110.96 (17)	C16—C15—C11	112.98 (17)
O20—C2—C3	111.62 (17)	C1—C15—C11	105.87 (17)
O20—C2—C1	103.89 (15)	C17—C15—C11	108.51 (18)
C3—C2—C1	119.76 (18)	C15—C16—H16A	109.5
O20—C2—H2	107.0	C15—C16—H16B	109.5
C3—C2—H2	107.0	H16A—C16—H16B	109.5
C1—C2—H2	107.0	C15—C16—H16C	109.5
C4—C3—C2	112.61 (17)	H16A—C16—H16C	109.5
C4—C3—C8	114.01 (17)	H16B—C16—H16C	109.5
C2—C3—C8	109.74 (17)	C15—C17—H17C	109.5
C4—C3—H3	106.7	C15—C17—H17A	109.5
C2—C3—H3	106.7	H17C—C17—H17A	109.5
C8—C3—H3	106.7	C15—C17—H17B	109.5
O34—C4—C5	109.67 (17)	H17C—C17—H17B	109.5
O34—C4—C3	105.90 (17)	H17A—C17—H17B	109.5
C5—C4—C3	111.98 (17)	C12—C18—H18B	109.5
O34—C4—H4	109.7	C12—C18—H18C	109.5
C5—C4—H4	109.7	H18B—C18—H18C	109.5
C3—C4—H4	109.7	C12—C18—H18A	109.5
C4—C5—C6	112.64 (18)	H18B—C18—H18A	109.5
C4—C5—H5A	109.1	H18C—C18—H18A	109.5
C6—C5—H5A	109.1	C8—C19—H19A	109.5
C4—C5—H5B	109.1	C8—C19—H19B	109.5
C6—C5—H5B	109.1	H19A—C19—H19B	109.5
H5A—C5—H5B	107.8	C8—C19—H19C	109.5
C7—C6—C5	109.07 (18)	H19A—C19—H19C	109.5
C7—C6—H6A	109.9	H19B—C19—H19C	109.5
C5—C6—H6A	109.9	C21—O20—C2	110.57 (17)
C7—C6—H6B	109.9	O23—C21—O22	124.3 (2)
C5—C6—H6B	109.9	O23—C21—O20	124.0 (2)
H6A—C6—H6B	108.3	O22—C21—O20	111.64 (18)
O24—C7—C6	110.13 (17)	C21—O22—C1	111.30 (16)
O24—C7—C8	106.08 (16)	C25—O24—C7	118.46 (17)
C6—C7—C8	113.65 (17)	O26—C25—O24	123.99 (19)
O24—C7—H7	109.0	O26—C25—C27	124.93 (19)
C6—C7—H7	109.0	O24—C25—C27	111.07 (19)
C8—C7—H7	109.0	C32—C27—C28	119.1 (2)
C19—C8—C7	110.53 (18)	C32—C27—C25	122.10 (19)
C19—C8—C3	112.58 (17)	C28—C27—C25	118.8 (2)
C7—C8—C3	107.06 (16)	C29—C28—C27	120.1 (2)
C19—C8—C9	110.29 (17)	C29—C28—H28	120.0
C7—C8—C9	106.03 (17)	C27—C28—H28	120.0
C3—C8—C9	110.09 (17)	C30—C29—C28	120.3 (2)
C10—C9—C8	119.09 (18)	C30—C29—H29	119.8
C10—C9—H9B	107.5	C28—C29—H29	119.8
C8—C9—H9B	107.5	C29—C30—C31	120.0 (2)
C10—C9—H9A	107.5	C29—C30—H30	120.0
C8—C9—H9A	107.5	C31—C30—H30	120.0
H9B—C9—H9A	107.0	C32—C31—C30	120.0 (2)
O33—C10—C9	119.8 (2)	C32—C31—H31	120.0
O33—C10—C11	118.8 (2)	C30—C31—H31	120.0
C9—C10—C11	121.29 (19)	C31—C32—C27	120.5 (2)
C12—C11—C10	112.27 (18)	C31—C32—H32	119.7
C12—C11—C15	111.64 (17)	C27—C32—H32	119.7
C10—C11—C15	114.89 (18)	C35—O34—C4	115.90 (17)
C12—C11—H11	105.7	O36—C35—O34	114.22 (17)
C10—C11—H11	105.7	O36—C35—H35A	108.7
C15—C11—H11	105.7	O34—C35—H35A	108.7
C13—C12—C18	123.5 (2)	O36—C35—H35B	108.7
C13—C12—C11	121.4 (2)	O34—C35—H35B	108.7
C18—C12—C11	115.12 (18)	H35A—C35—H35B	107.6
C12—C13—C14	124.3 (2)	C35—O36—C37	113.22 (18)
C12—C13—H13	117.9	O36—C37—H37B	109.5
C14—C13—H13	117.9	O36—C37—H37C	109.5
C13—C14—C1	112.63 (17)	H37B—C37—H37C	109.5
C13—C14—H14A	109.1	O36—C37—H37A	109.5
C1—C14—H14A	109.1	H37B—C37—H37A	109.5
C13—C14—H14B	109.1	H37C—C37—H37A	109.5

O22—C1—C2—O20	3.79 (19)	O22—C1—C14—C13	161.48 (17)
C14—C1—C2—O20	−111.28 (19)	C15—C1—C14—C13	42.9 (2)
C15—C1—C2—O20	120.08 (18)	C2—C1—C14—C13	−85.5 (2)
O22—C1—C2—C3	129.13 (18)	O22—C1—C15—C16	55.9 (2)
C14—C1—C2—C3	14.1 (3)	C14—C1—C15—C16	172.61 (17)
C15—C1—C2—C3	−114.6 (2)	C2—C1—C15—C16	−56.1 (2)
O20—C2—C3—C4	7.8 (2)	O22—C1—C15—C17	−63.0 (2)
C1—C2—C3—C4	−113.8 (2)	C14—C1—C15—C17	53.7 (2)
O20—C2—C3—C8	−120.39 (18)	C2—C1—C15—C17	−175.02 (17)
C1—C2—C3—C8	118.0 (2)	O22—C1—C15—C11	179.44 (16)
C2—C3—C4—O34	63.5 (2)	C14—C1—C15—C11	−63.9 (2)
C8—C3—C4—O34	−170.62 (16)	C2—C1—C15—C11	67.4 (2)
C2—C3—C4—C5	−177.00 (18)	C12—C11—C15—C16	176.93 (18)
C8—C3—C4—C5	−51.1 (2)	C10—C11—C15—C16	47.6 (3)
O34—C4—C5—C6	169.18 (18)	C12—C11—C15—C1	54.1 (2)
C3—C4—C5—C6	51.9 (3)	C10—C11—C15—C1	−75.2 (2)
C4—C5—C6—C7	−55.8 (2)	C12—C11—C15—C17	−65.1 (2)
C5—C6—C7—O24	179.09 (17)	C10—C11—C15—C17	165.54 (18)
C5—C6—C7—C8	60.2 (2)	C3—C2—O20—C21	−131.96 (18)
O24—C7—C8—C19	−55.8 (2)	C1—C2—O20—C21	−1.6 (2)
C6—C7—C8—C19	65.3 (2)	C2—O20—C21—O23	178.3 (2)
O24—C7—C8—C3	−178.79 (16)	C2—O20—C21—O22	−1.6 (2)
C6—C7—C8—C3	−57.6 (2)	O23—C21—O22—C1	−175.5 (2)
O24—C7—C8—C9	63.7 (2)	O20—C21—O22—C1	4.4 (2)
C6—C7—C8—C9	−175.17 (17)	C14—C1—O22—C21	117.38 (19)
C4—C3—C8—C19	−69.6 (2)	C15—C1—O22—C21	−122.62 (19)
C2—C3—C8—C19	57.8 (2)	C2—C1—O22—C21	−5.0 (2)
C4—C3—C8—C7	52.1 (2)	C6—C7—O24—C25	86.3 (2)
C2—C3—C8—C7	179.44 (17)	C8—C7—O24—C25	−150.29 (18)
C4—C3—C8—C9	166.90 (18)	C7—O24—C25—O26	−2.7 (3)
C2—C3—C8—C9	−65.7 (2)	C7—O24—C25—C27	175.64 (17)
C19—C8—C9—C10	−63.2 (2)	O26—C25—C27—C32	−171.9 (2)
C7—C8—C9—C10	177.06 (18)	O24—C25—C27—C32	9.8 (3)
C3—C8—C9—C10	61.6 (2)	O26—C25—C27—C28	9.1 (3)
C8—C9—C10—O33	86.1 (2)	O24—C25—C27—C28	−169.24 (19)
C8—C9—C10—C11	−98.0 (2)	C32—C27—C28—C29	−1.1 (3)
O33—C10—C11—C12	158.08 (19)	C25—C27—C28—C29	177.9 (2)
C9—C10—C11—C12	−17.9 (3)	C27—C28—C29—C30	0.4 (3)
O33—C10—C11—C15	−72.9 (3)	C28—C29—C30—C31	0.7 (4)
C9—C10—C11—C15	111.1 (2)	C29—C30—C31—C32	−1.0 (4)
C10—C11—C12—C13	104.9 (2)	C30—C31—C32—C27	0.2 (4)
C15—C11—C12—C13	−25.8 (3)	C28—C27—C32—C31	0.8 (3)
C10—C11—C12—C18	−75.4 (2)	C25—C27—C32—C31	−178.2 (2)
C15—C11—C12—C18	153.96 (19)	C5—C4—O34—C35	100.2 (2)
C18—C12—C13—C14	−176.4 (2)	C3—C4—O34—C35	−138.79 (18)
C11—C12—C13—C14	3.3 (3)	C4—O34—C35—O36	−72.6 (2)
C12—C13—C14—C1	−11.5 (3)	O34—C35—O36—C37	−68.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O34	0.99	2.65	3.479 (3)	142
C31—H31···O33ⁱ	0.95	2.35	3.147 (3)	141
C19—H19C···O23ⁱⁱ	0.98	2.43	3.310 (3)	149
C16—H16A···O23ⁱⁱ	0.98	2.56	3.491 (3)	158

Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+2, −y+1, −z+1.

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Crystal structures of (±)-(1SR,5SR,6SR,7SR,10SR,11SR,13RS,14SR)-13-hy­droxy-7-meth­oxy­meth­oxy-11,15,18,18-tetra­methyl-3-oxo-2,4-dioxa­tetra­cyclo­[12.3.1.01,5.06,11]octa­dec-15-en-10-yl benzoate, its 13-epimer and 13-one derivative

Supporting information

Key indicators

checkCIF/PLATON results

Crystal structures of (±)-(1SR,5SR,6SR,7SR,10SR,11SR,13RS,14SR)-13-hydroxy-7-methoxymethoxy-11,15,18,18-tetramethyl-3-oxo-2,4-dioxatetracyclo[12.3.1.0^1,5.0^6,11]octadec-15-en-10-yl benzoate, its 13-epimer and 13-one derivative