Single-crystal-to-single-crystal phase transition of 18β-glycyrrhetinic acid isopropyl ester

Langer, D.; Wicher, B.; Tykarska, E.

doi:10.1107/S2052520622002517

Single-crystal-to-single-crystal phase transition of 18β-glycyrrhetinic acid isopropyl ester

Due to the destruction of the integrity of the parent crystal, single-crystal-to-single-crystal phase transition in organic compounds is still a relatively rare phenomenon. The phase transition in glycyrrhetinic acid isopropyl ester is triggered by temperature change. The increasing volume of the isopropyl substituent as a result of increasing temperature forces a remodelling of the structural motifs. These changes cause a single-crystal-to-single-crystal phase transition. The low-temperature form is isostructural with glycyrrhetinic acid methanol solvate, while the high-temperature phase is isostructural with the ethyl ester of this acid.

Keywords: triterpene; phase transition; glycyrrhetinic acid; crystal structure; differential scanning calorimetry; DSC.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520622002517/rm5058sup1.cif Contains datablocks P_11_18, P-13-17, 18b_et, 2-morpholinoethyl-GE
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520622002517/rm5058P_11_18sup2.hkl Contains datablock P_11_18
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520622002517/rm5058P_13_17sup3.hkl Contains datablock P_13_17
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520622002517/rm505818b_etsup4.hkl Contains datablock 18b_et
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520622002517/rm50582-morpholinoethyl-GEsup5.hkl Contains datablock 2-morpholinoethyl-GE
	Portable Document Format (PDF) file https://doi.org/10.1107/S2052520622002517/rm5058sup6.pdf Additional figures and tables

CCDC references: 2156220; 2156219; 2156218; 2156217

Computing details top

Data collection: CrysAlis PRO 1.171.38.34a (Rigaku OD, 2015) for P_11_18, P-13-17; CrysAlis PRO 1.171.41.93a (Rigaku OD, 2020) for 18b_et, 2-morpholinoethyl-GE. Cell refinement: CrysAlis PRO 1.171.38.34a (Rigaku OD, 2015) for P_11_18, P-13-17; CrysAlis PRO 1.171.41.93a (Rigaku OD, 2020) for 18b_et, 2-morpholinoethyl-GE. Data reduction: CrysAlis PRO 1.171.38.34a (Rigaku OD, 2015) for P_11_18, P-13-17; CrysAlis PRO 1.171.41.93a (Rigaku OD, 2020) for 18b_et, 2-morpholinoethyl-GE. Program(s) used to solve structure: SHELXT 2014/5 (Sheldrick, 2014) for P_11_18, P-13-17; SHELXT 2018/2 (Sheldrick, 2018) for 18b_et, 2-morpholinoethyl-GE. For all structures, program(s) used to refine structure: SHELXL 2018/3 (Sheldrick, 2015). Molecular graphics: Olex2 1.5 (Dolomanov et al., 2009) for P_11_18, 18b_et, 2-morpholinoethyl-GE; Olex2 1.3 (Dolomanov et al., 2009) for P-13-17. Software used to prepare material for publication: Olex2 1.5 (Dolomanov et al., 2009) for P_11_18, 18b_et, 2-morpholinoethyl-GE; Olex2 1.3 (Dolomanov et al., 2009) for P-13-17.

(P_11_18) top

Crystal data top

C₃₃H₅₂O₄	D_x = 1.154 Mg m⁻³
M_r = 512.74	Melting point: 484.8 K
Orthorhombic, P2₁2₁2₁	Cu Kα radiation, λ = 1.54184 Å
a = 11.8862 (3) Å	Cell parameters from 4055 reflections
b = 13.1419 (3) Å	θ = 4.1–76.2°
c = 18.8884 (4) Å	µ = 0.57 mm⁻¹
V = 2950.51 (12) Å³	T = 298 K
Z = 4	Block, colorless
F(000) = 1128	0.43 × 0.4 × 0.2 mm

Data collection top

SuperNova, Dual, Cu at zero, Atlas diffractometer	5087 reflections with I > 2σ(I)
Detector resolution: 10.3991 pixels mm^-1	R_int = 0.023
ω scans	θ_max = 76.5°, θ_min = 4.1°
Absorption correction: multi-scan CrysAlisPro 1.171.38.34a (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −10→14
T_min = 0.879, T_max = 1.000	k = −16→14
9671 measured reflections	l = −21→23
5641 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.039	w = 1/[σ²(F_o²) + (0.0629P)² + 0.0678P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.114	(Δ/σ)_max < 0.001
S = 1.08	Δρ_max = 0.15 e Å⁻³
5641 reflections	Δρ_min = −0.16 e Å⁻³
344 parameters	Absolute structure: Flack x determined using 1834 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
0 restraints	Absolute structure parameter: −0.11 (13)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
C1	0.57150 (19)	−0.02939 (17)	0.67473 (12)	0.0446 (5)
H1A	0.499843	0.005315	0.679308	0.054*
H1B	0.585066	−0.040676	0.624706	0.054*
C2	0.5640 (2)	−0.13297 (18)	0.71234 (13)	0.0491 (5)
H2A	0.544545	−0.122492	0.761679	0.059*
H2B	0.504963	−0.173359	0.690745	0.059*
C3	0.6740 (2)	−0.18986 (17)	0.70780 (13)	0.0478 (5)
H3	0.691171	−0.196486	0.657268	0.057*
C4	0.7725 (2)	−0.13093 (18)	0.74076 (12)	0.0455 (5)
C5	0.77645 (18)	−0.02357 (16)	0.70560 (11)	0.0396 (4)
H5	0.791503	−0.037865	0.655568	0.048*
C6	0.8754 (2)	0.04277 (19)	0.72856 (13)	0.0499 (5)
H6A	0.859168	0.073563	0.774100	0.060*
H6B	0.942285	0.001075	0.733608	0.060*
C7	0.89649 (19)	0.12584 (17)	0.67370 (13)	0.0469 (5)
H7A	0.917794	0.094155	0.629298	0.056*
H7B	0.959188	0.167430	0.689300	0.056*
C8	0.79399 (17)	0.19509 (16)	0.66076 (11)	0.0398 (4)
C9	0.68591 (17)	0.12961 (15)	0.65064 (10)	0.0366 (4)
H9	0.697524	0.095459	0.605105	0.044*
C10	0.66514 (17)	0.03978 (16)	0.70441 (10)	0.0383 (4)
C11	0.58604 (18)	0.20051 (16)	0.63737 (11)	0.0404 (4)
C12	0.60928 (19)	0.29910 (17)	0.60353 (12)	0.0436 (4)
H12	0.548654	0.342605	0.596273	0.052*
C13	0.71032 (19)	0.33109 (15)	0.58241 (10)	0.0395 (4)
C14	0.81233 (18)	0.26110 (15)	0.59130 (11)	0.0404 (4)
C15	0.9247 (2)	0.32109 (19)	0.59582 (15)	0.0522 (5)
H15A	0.935488	0.343904	0.644191	0.063*
H15B	0.986218	0.275505	0.584262	0.063*
C16	0.9300 (2)	0.41348 (19)	0.54655 (15)	0.0549 (6)
H16A	1.000602	0.448893	0.554033	0.066*
H16B	0.928352	0.390308	0.497800	0.066*
C17	0.8326 (2)	0.48756 (17)	0.55873 (13)	0.0510 (5)
C18	0.7200 (2)	0.43301 (16)	0.54467 (11)	0.0435 (5)
H18	0.660667	0.476747	0.564007	0.052*
C19	0.6927 (2)	0.41755 (16)	0.46510 (11)	0.0429 (4)
H19A	0.741917	0.365191	0.446407	0.051*
H19B	0.615966	0.393054	0.460894	0.051*
C20	0.7054 (2)	0.51360 (17)	0.41950 (12)	0.0475 (5)
C21	0.8232 (3)	0.5562 (2)	0.43132 (15)	0.0602 (6)
H21A	0.832427	0.617758	0.403566	0.072*
H21B	0.878425	0.507087	0.415120	0.072*
C22	0.8444 (3)	0.5802 (2)	0.50928 (16)	0.0631 (7)
H22A	0.791700	0.632289	0.524307	0.076*
H22B	0.919650	0.607864	0.514201	0.076*
C23	0.7643 (3)	−0.1281 (2)	0.82220 (13)	0.0619 (7)
H23A	0.690505	−0.105827	0.835870	0.093*
H23B	0.819486	−0.081867	0.840622	0.093*
H23C	0.777730	−0.195019	0.840824	0.093*
C24	0.8807 (2)	−0.1886 (2)	0.72164 (16)	0.0589 (6)
H24A	0.874057	−0.258205	0.736441	0.088*
H24B	0.943512	−0.157578	0.745180	0.088*
H24C	0.892059	−0.185989	0.671360	0.088*
C25	0.6267 (2)	0.07849 (19)	0.77747 (12)	0.0507 (5)
H25A	0.577516	0.135807	0.771428	0.076*
H25B	0.691157	0.098615	0.804667	0.076*
H25C	0.587321	0.025175	0.801849	0.076*
C26	0.7814 (2)	0.26503 (19)	0.72650 (12)	0.0514 (5)
H26A	0.785951	0.224711	0.768785	0.077*
H26B	0.709869	0.298878	0.724815	0.077*
H26C	0.840558	0.314751	0.726559	0.077*
C27	0.8199 (2)	0.19506 (17)	0.52336 (12)	0.0468 (5)
H27A	0.867830	0.137599	0.532029	0.070*
H27B	0.850460	0.235037	0.485414	0.070*
H27C	0.746114	0.171700	0.510610	0.070*
C28	0.8329 (3)	0.5277 (2)	0.63519 (16)	0.0692 (8)
H28A	0.818981	0.472478	0.667285	0.104*
H28B	0.775202	0.578208	0.640491	0.104*
H28C	0.904835	0.557473	0.645548	0.104*
C29	0.6898 (3)	0.4854 (2)	0.34080 (13)	0.0612 (6)
H29A	0.743132	0.433729	0.327985	0.092*
H29B	0.701688	0.544620	0.312000	0.092*
H29C	0.614847	0.460295	0.333445	0.092*
C30	0.6206 (3)	0.59701 (18)	0.43537 (13)	0.0539 (6)
C31	0.4528 (3)	0.6439 (2)	0.49685 (13)	0.0592 (7)
H31	0.441145	0.694716	0.459585	0.071*
C32	0.5037 (4)	0.6941 (3)	0.56065 (18)	0.0831 (10)
H32A	0.449534	0.738945	0.581801	0.125*
H32B	0.568759	0.732482	0.546599	0.125*
H32C	0.525477	0.643094	0.594334	0.125*
C33	0.3429 (3)	0.5915 (3)	0.51309 (19)	0.0782 (9)
H33A	0.355174	0.539423	0.547886	0.117*
H33B	0.313549	0.561386	0.470628	0.117*
H33C	0.290084	0.640321	0.531078	0.117*
O3	0.66523 (18)	−0.29051 (13)	0.73467 (12)	0.0628 (5)
H3A	0.625541	−0.290447	0.770180	0.094*
O11	0.48877 (14)	0.17854 (13)	0.65179 (10)	0.0549 (4)
O30	0.52988 (16)	0.56523 (12)	0.47137 (9)	0.0517 (4)
O31	0.6337 (2)	0.68391 (15)	0.41726 (15)	0.0865 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0429 (11)	0.0450 (11)	0.0461 (10)	−0.0021 (9)	−0.0039 (9)	0.0071 (9)
C2	0.0470 (12)	0.0467 (11)	0.0535 (12)	−0.0045 (10)	−0.0007 (10)	0.0081 (10)
C3	0.0547 (12)	0.0409 (10)	0.0477 (11)	−0.0004 (10)	0.0058 (10)	0.0047 (9)
C4	0.0489 (12)	0.0452 (11)	0.0424 (10)	0.0051 (10)	−0.0015 (9)	0.0065 (9)
C5	0.0409 (10)	0.0424 (10)	0.0356 (9)	0.0030 (8)	−0.0025 (8)	0.0032 (8)
C6	0.0441 (11)	0.0526 (12)	0.0529 (12)	0.0018 (10)	−0.0122 (10)	0.0052 (10)
C7	0.0383 (10)	0.0454 (11)	0.0569 (12)	−0.0014 (9)	−0.0071 (9)	0.0023 (10)
C8	0.0404 (10)	0.0388 (9)	0.0401 (9)	0.0004 (8)	−0.0042 (8)	−0.0015 (8)
C9	0.0377 (9)	0.0382 (9)	0.0337 (8)	0.0030 (8)	−0.0014 (8)	−0.0011 (7)
C10	0.0387 (10)	0.0418 (9)	0.0344 (9)	0.0017 (8)	−0.0014 (8)	0.0023 (8)
C11	0.0406 (10)	0.0414 (10)	0.0391 (9)	0.0040 (9)	0.0017 (8)	0.0006 (8)
C12	0.0437 (11)	0.0414 (10)	0.0456 (10)	0.0072 (9)	0.0023 (9)	0.0055 (8)
C13	0.0458 (11)	0.0364 (9)	0.0361 (8)	0.0027 (8)	−0.0009 (8)	−0.0047 (8)
C14	0.0390 (10)	0.0381 (9)	0.0442 (10)	−0.0008 (8)	0.0002 (8)	−0.0002 (8)
C15	0.0432 (11)	0.0471 (12)	0.0665 (14)	−0.0041 (10)	−0.0048 (11)	0.0047 (11)
C16	0.0476 (12)	0.0503 (12)	0.0669 (15)	−0.0128 (10)	−0.0028 (11)	0.0045 (11)
C17	0.0598 (14)	0.0402 (10)	0.0530 (12)	−0.0075 (10)	−0.0051 (11)	−0.0012 (9)
C18	0.0509 (11)	0.0369 (9)	0.0427 (10)	0.0007 (9)	0.0032 (9)	0.0002 (8)
C19	0.0472 (11)	0.0381 (9)	0.0434 (10)	−0.0025 (9)	0.0019 (9)	0.0008 (8)
C20	0.0550 (13)	0.0439 (10)	0.0436 (10)	−0.0046 (10)	0.0054 (10)	0.0040 (9)
C21	0.0631 (15)	0.0558 (13)	0.0617 (14)	−0.0136 (12)	0.0058 (12)	0.0125 (11)
C22	0.0724 (17)	0.0443 (12)	0.0726 (16)	−0.0159 (12)	−0.0091 (14)	0.0065 (12)
C23	0.0789 (18)	0.0627 (15)	0.0441 (11)	0.0066 (14)	−0.0060 (12)	0.0138 (11)
C24	0.0543 (14)	0.0535 (14)	0.0691 (15)	0.0135 (11)	0.0003 (12)	0.0116 (12)
C25	0.0592 (13)	0.0551 (12)	0.0379 (10)	0.0081 (11)	0.0055 (10)	0.0013 (9)
C26	0.0654 (15)	0.0465 (11)	0.0422 (10)	−0.0044 (11)	−0.0088 (10)	−0.0059 (9)
C27	0.0502 (11)	0.0446 (10)	0.0456 (10)	0.0033 (10)	0.0071 (9)	−0.0018 (9)
C28	0.095 (2)	0.0516 (13)	0.0611 (15)	−0.0043 (15)	−0.0149 (15)	−0.0095 (12)
C29	0.0761 (17)	0.0646 (14)	0.0427 (11)	−0.0035 (14)	0.0060 (12)	0.0074 (11)
C30	0.0699 (16)	0.0442 (11)	0.0477 (11)	0.0003 (11)	0.0017 (11)	0.0078 (10)
C31	0.0834 (19)	0.0502 (13)	0.0439 (11)	0.0232 (13)	0.0007 (12)	−0.0008 (10)
C32	0.116 (3)	0.0693 (17)	0.0635 (16)	0.028 (2)	−0.0111 (18)	−0.0200 (15)
C33	0.079 (2)	0.088 (2)	0.0679 (17)	0.0220 (18)	0.0120 (16)	−0.0097 (16)
O3	0.0702 (12)	0.0422 (8)	0.0760 (12)	0.0024 (8)	0.0146 (10)	0.0110 (8)
O11	0.0399 (8)	0.0541 (9)	0.0707 (10)	0.0060 (7)	0.0084 (8)	0.0110 (8)
O30	0.0654 (10)	0.0408 (7)	0.0489 (8)	0.0087 (8)	0.0087 (8)	0.0030 (7)
O31	0.1047 (18)	0.0474 (10)	0.1075 (18)	0.0032 (11)	0.0181 (15)	0.0299 (11)

Geometric parameters (Å, º) top

C1—H1A	0.9700	C18—C19	1.551 (3)
C1—H1B	0.9700	C19—H19A	0.9700
C1—C2	1.538 (3)	C19—H19B	0.9700
C1—C10	1.542 (3)	C19—C20	1.536 (3)
C2—H2A	0.9700	C20—C21	1.525 (4)
C2—H2B	0.9700	C20—C29	1.543 (3)
C2—C3	1.508 (3)	C20—C30	1.519 (4)
C3—H3	0.9800	C21—H21A	0.9700
C3—C4	1.536 (3)	C21—H21B	0.9700
C3—O3	1.421 (3)	C21—C22	1.527 (4)
C4—C5	1.560 (3)	C22—H22A	0.9700
C4—C23	1.542 (3)	C22—H22B	0.9700
C4—C24	1.536 (3)	C23—H23A	0.9600
C5—H5	0.9800	C23—H23B	0.9600
C5—C6	1.527 (3)	C23—H23C	0.9600
C5—C10	1.563 (3)	C24—H24A	0.9600
C6—H6A	0.9700	C24—H24B	0.9600
C6—H6B	0.9700	C24—H24C	0.9600
C6—C7	1.526 (3)	C25—H25A	0.9600
C7—H7A	0.9700	C25—H25B	0.9600
C7—H7B	0.9700	C25—H25C	0.9600
C7—C8	1.540 (3)	C26—H26A	0.9600
C8—C9	1.558 (3)	C26—H26B	0.9600
C8—C14	1.588 (3)	C26—H26C	0.9600
C8—C26	1.552 (3)	C27—H27A	0.9600
C9—H9	0.9800	C27—H27B	0.9600
C9—C10	1.577 (3)	C27—H27C	0.9600
C9—C11	1.530 (3)	C28—H28A	0.9600
C10—C25	1.540 (3)	C28—H28B	0.9600
C11—C12	1.471 (3)	C28—H28C	0.9600
C11—O11	1.222 (3)	C29—H29A	0.9600
C12—H12	0.9300	C29—H29B	0.9600
C12—C13	1.333 (3)	C29—H29C	0.9600
C13—C14	1.531 (3)	C30—O30	1.342 (3)
C13—C18	1.522 (3)	C30—O31	1.202 (3)
C14—C15	1.554 (3)	C31—H31	0.9800
C14—C27	1.552 (3)	C31—C32	1.501 (4)
C15—H15A	0.9700	C31—C33	1.509 (5)
C15—H15B	0.9700	C31—O30	1.463 (3)
C15—C16	1.531 (3)	C32—H32A	0.9600
C16—H16A	0.9700	C32—H32B	0.9600
C16—H16B	0.9700	C32—H32C	0.9600
C16—C17	1.530 (4)	C33—H33A	0.9600
C17—C18	1.542 (3)	C33—H33B	0.9600
C17—C22	1.541 (3)	C33—H33C	0.9600
C17—C28	1.538 (4)	O3—H3A	0.8200
C18—H18	0.9800

H1A—C1—H1B	107.7	C13—C18—H18	106.7
C2—C1—H1A	108.9	C13—C18—C19	108.84 (17)
C2—C1—H1B	108.9	C17—C18—H18	106.7
C2—C1—C10	113.29 (18)	C17—C18—C19	114.17 (19)
C10—C1—H1A	108.9	C19—C18—H18	106.7
C10—C1—H1B	108.9	C18—C19—H19A	108.6
C1—C2—H2A	109.4	C18—C19—H19B	108.6
C1—C2—H2B	109.4	H19A—C19—H19B	107.6
H2A—C2—H2B	108.0	C20—C19—C18	114.53 (18)
C3—C2—C1	111.25 (19)	C20—C19—H19A	108.6
C3—C2—H2A	109.4	C20—C19—H19B	108.6
C3—C2—H2B	109.4	C19—C20—C29	109.33 (19)
C2—C3—H3	106.3	C21—C20—C19	108.1 (2)
C2—C3—C4	112.81 (19)	C21—C20—C29	109.9 (2)
C4—C3—H3	106.3	C30—C20—C19	114.66 (19)
O3—C3—C2	112.2 (2)	C30—C20—C21	108.4 (2)
O3—C3—H3	106.3	C30—C20—C29	106.5 (2)
O3—C3—C4	112.4 (2)	C20—C21—H21A	109.3
C3—C4—C5	107.85 (18)	C20—C21—H21B	109.3
C3—C4—C23	111.6 (2)	C20—C21—C22	111.6 (2)
C23—C4—C5	113.9 (2)	H21A—C21—H21B	108.0
C24—C4—C3	107.1 (2)	C22—C21—H21A	109.3
C24—C4—C5	108.71 (19)	C22—C21—H21B	109.3
C24—C4—C23	107.4 (2)	C17—C22—H22A	108.8
C4—C5—H5	104.0	C17—C22—H22B	108.8
C4—C5—C10	117.53 (18)	C21—C22—C17	114.0 (2)
C6—C5—C4	114.75 (18)	C21—C22—H22A	108.8
C6—C5—H5	104.0	C21—C22—H22B	108.8
C6—C5—C10	110.61 (18)	H22A—C22—H22B	107.7
C10—C5—H5	104.0	C4—C23—H23A	109.5
C5—C6—H6A	109.7	C4—C23—H23B	109.5
C5—C6—H6B	109.7	C4—C23—H23C	109.5
H6A—C6—H6B	108.2	H23A—C23—H23B	109.5
C7—C6—C5	110.00 (18)	H23A—C23—H23C	109.5
C7—C6—H6A	109.7	H23B—C23—H23C	109.5
C7—C6—H6B	109.7	C4—C24—H24A	109.5
C6—C7—H7A	108.8	C4—C24—H24B	109.5
C6—C7—H7B	108.8	C4—C24—H24C	109.5
C6—C7—C8	113.62 (19)	H24A—C24—H24B	109.5
H7A—C7—H7B	107.7	H24A—C24—H24C	109.5
C8—C7—H7A	108.8	H24B—C24—H24C	109.5
C8—C7—H7B	108.8	C10—C25—H25A	109.5
C7—C8—C9	110.20 (16)	C10—C25—H25B	109.5
C7—C8—C14	110.20 (17)	C10—C25—H25C	109.5
C7—C8—C26	107.41 (18)	H25A—C25—H25B	109.5
C9—C8—C14	108.28 (15)	H25A—C25—H25C	109.5
C26—C8—C9	110.22 (18)	H25B—C25—H25C	109.5
C26—C8—C14	110.54 (17)	C8—C26—H26A	109.5
C8—C9—H9	104.1	C8—C26—H26B	109.5
C8—C9—C10	117.63 (16)	C8—C26—H26C	109.5
C10—C9—H9	104.1	H26A—C26—H26B	109.5
C11—C9—C8	108.88 (16)	H26A—C26—H26C	109.5
C11—C9—H9	104.1	H26B—C26—H26C	109.5
C11—C9—C10	116.11 (17)	C14—C27—H27A	109.5
C1—C10—C5	107.59 (17)	C14—C27—H27B	109.5
C1—C10—C9	108.68 (16)	C14—C27—H27C	109.5
C5—C10—C9	105.99 (16)	H27A—C27—H27B	109.5
C25—C10—C1	107.82 (19)	H27A—C27—H27C	109.5
C25—C10—C5	114.47 (17)	H27B—C27—H27C	109.5
C25—C10—C9	112.10 (17)	C17—C28—H28A	109.5
C12—C11—C9	117.51 (18)	C17—C28—H28B	109.5
O11—C11—C9	123.62 (19)	C17—C28—H28C	109.5
O11—C11—C12	118.8 (2)	H28A—C28—H28B	109.5
C11—C12—H12	117.4	H28A—C28—H28C	109.5
C13—C12—C11	125.2 (2)	H28B—C28—H28C	109.5
C13—C12—H12	117.4	C20—C29—H29A	109.5
C12—C13—C14	119.41 (18)	C20—C29—H29B	109.5
C12—C13—C18	119.0 (2)	C20—C29—H29C	109.5
C18—C13—C14	121.37 (19)	H29A—C29—H29B	109.5
C13—C14—C8	108.06 (17)	H29A—C29—H29C	109.5
C13—C14—C15	112.46 (17)	H29B—C29—H29C	109.5
C13—C14—C27	106.93 (17)	O30—C30—C20	114.12 (19)
C15—C14—C8	110.48 (18)	O31—C30—C20	122.9 (3)
C27—C14—C8	112.69 (16)	O31—C30—O30	122.9 (3)
C27—C14—C15	106.23 (19)	C32—C31—H31	109.5
C14—C15—H15A	108.8	C32—C31—C33	112.7 (3)
C14—C15—H15B	108.8	C33—C31—H31	109.5
H15A—C15—H15B	107.7	O30—C31—H31	109.5
C16—C15—C14	113.8 (2)	O30—C31—C32	108.8 (3)
C16—C15—H15A	108.8	O30—C31—C33	106.6 (2)
C16—C15—H15B	108.8	C31—C32—H32A	109.5
C15—C16—H16A	109.1	C31—C32—H32B	109.5
C15—C16—H16B	109.1	C31—C32—H32C	109.5
H16A—C16—H16B	107.8	H32A—C32—H32B	109.5
C17—C16—C15	112.5 (2)	H32A—C32—H32C	109.5
C17—C16—H16A	109.1	H32B—C32—H32C	109.5
C17—C16—H16B	109.1	C31—C33—H33A	109.5
C16—C17—C18	109.59 (18)	C31—C33—H33B	109.5
C16—C17—C22	110.1 (2)	C31—C33—H33C	109.5
C16—C17—C28	111.0 (2)	H33A—C33—H33B	109.5
C22—C17—C18	110.0 (2)	H33A—C33—H33C	109.5
C28—C17—C18	108.9 (2)	H33B—C33—H33C	109.5
C28—C17—C22	107.3 (2)	C3—O3—H3A	109.5
C13—C18—C17	113.20 (19)	C30—O30—C31	116.7 (2)

C1—C2—C3—C4	58.9 (3)	C14—C8—C9—C10	166.28 (16)
C1—C2—C3—O3	−173.0 (2)	C14—C8—C9—C11	−59.0 (2)
C2—C1—C10—C5	51.2 (2)	C14—C13—C18—C17	−36.3 (3)
C2—C1—C10—C9	165.55 (18)	C14—C13—C18—C19	91.8 (2)
C2—C1—C10—C25	−72.7 (2)	C14—C15—C16—C17	55.9 (3)
C2—C3—C4—C5	−53.9 (2)	C15—C16—C17—C18	−60.6 (3)
C2—C3—C4—C23	71.9 (2)	C15—C16—C17—C22	178.3 (2)
C2—C3—C4—C24	−170.78 (19)	C15—C16—C17—C28	59.7 (3)
C3—C4—C5—C6	−175.76 (19)	C16—C17—C18—C13	49.3 (3)
C3—C4—C5—C10	51.6 (2)	C16—C17—C18—C19	−76.0 (2)
C4—C5—C6—C7	159.23 (19)	C16—C17—C22—C21	70.2 (3)
C4—C5—C10—C1	−50.3 (2)	C17—C18—C19—C20	−49.3 (3)
C4—C5—C10—C9	−166.45 (17)	C18—C13—C14—C8	152.03 (18)
C4—C5—C10—C25	69.5 (2)	C18—C13—C14—C15	29.8 (3)
C5—C6—C7—C8	58.2 (3)	C18—C13—C14—C27	−86.4 (2)
C6—C5—C10—C1	175.21 (17)	C18—C17—C22—C21	−50.7 (3)
C6—C5—C10—C9	59.1 (2)	C18—C19—C20—C21	53.8 (3)
C6—C5—C10—C25	−65.0 (2)	C18—C19—C20—C29	173.3 (2)
C6—C7—C8—C9	−47.1 (2)	C18—C19—C20—C30	−67.2 (3)
C6—C7—C8—C14	−166.51 (18)	C19—C20—C21—C22	−57.9 (3)
C6—C7—C8—C26	73.0 (2)	C19—C20—C30—O30	−17.8 (3)
C7—C8—C9—C10	45.7 (2)	C19—C20—C30—O31	162.2 (3)
C7—C8—C9—C11	−179.58 (17)	C20—C21—C22—C17	59.2 (3)
C7—C8—C14—C13	−177.98 (17)	C20—C30—O30—C31	171.7 (2)
C7—C8—C14—C15	−54.6 (2)	C21—C20—C30—O30	−138.6 (2)
C7—C8—C14—C27	64.1 (2)	C21—C20—C30—O31	41.4 (4)
C8—C9—C10—C1	−166.62 (17)	C22—C17—C18—C13	170.4 (2)
C8—C9—C10—C5	−51.2 (2)	C22—C17—C18—C19	45.1 (3)
C8—C9—C10—C25	74.3 (2)	C23—C4—C5—C6	59.8 (3)
C8—C9—C11—C12	28.5 (2)	C23—C4—C5—C10	−72.9 (3)
C8—C9—C11—O11	−153.3 (2)	C24—C4—C5—C6	−59.9 (3)
C8—C14—C15—C16	−158.9 (2)	C24—C4—C5—C10	167.43 (19)
C9—C8—C14—C13	61.4 (2)	C26—C8—C9—C10	−72.7 (2)
C9—C8—C14—C15	−175.16 (18)	C26—C8—C9—C11	62.0 (2)
C9—C8—C14—C27	−56.5 (2)	C26—C8—C14—C13	−59.4 (2)
C9—C11—C12—C13	1.1 (3)	C26—C8—C14—C15	64.0 (2)
C10—C1—C2—C3	−57.8 (3)	C26—C8—C14—C27	−177.33 (19)
C10—C5—C6—C7	−65.0 (2)	C27—C14—C15—C16	78.5 (2)
C10—C9—C11—C12	164.00 (18)	C28—C17—C18—C13	−72.2 (2)
C10—C9—C11—O11	−17.8 (3)	C28—C17—C18—C19	162.5 (2)
C11—C9—C10—C1	61.8 (2)	C28—C17—C22—C21	−169.0 (3)
C11—C9—C10—C5	177.22 (17)	C29—C20—C21—C22	−177.1 (2)
C11—C9—C10—C25	−57.2 (2)	C29—C20—C30—O30	103.3 (2)
C11—C12—C13—C14	1.7 (3)	C29—C20—C30—O31	−76.7 (3)
C11—C12—C13—C18	176.8 (2)	C30—C20—C21—C22	66.9 (3)
C12—C13—C14—C8	−32.9 (3)	C32—C31—O30—C30	−76.4 (3)
C12—C13—C14—C15	−155.1 (2)	C33—C31—O30—C30	161.7 (2)
C12—C13—C14—C27	88.6 (2)	O3—C3—C4—C5	178.03 (18)
C12—C13—C18—C17	148.6 (2)	O3—C3—C4—C23	−56.1 (3)
C12—C13—C18—C19	−83.3 (2)	O3—C3—C4—C24	61.2 (2)
C13—C14—C15—C16	−38.1 (3)	O11—C11—C12—C13	−177.2 (2)
C13—C18—C19—C20	−176.85 (19)	O31—C30—O30—C31	−8.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O11ⁱ	0.82	2.05	2.849 (3)	166

Symmetry code: (i) −x+1, y−1/2, −z+3/2.

(P-13-17) top

Crystal data top

C₃₃H₅₂O₄	D_x = 1.133 Mg m⁻³
M_r = 512.74	Melting point: 484.8 K
Orthorhombic, P2₁2₁2₁	Cu Kα radiation, λ = 1.54184 Å
a = 13.1807 (3) Å	Cell parameters from 12238 reflections
b = 13.2466 (4) Å	θ = 4.2–76.0°
c = 17.2198 (5) Å	µ = 0.56 mm⁻¹
V = 3006.57 (13) Å³	T = 298 K
Z = 4	Block, colorless
F(000) = 1128	0.4 × 0.3 × 0.2 mm

Data collection top

SuperNova, Dual, Cu at zero, Atlas diffractometer	5936 independent reflections
Radiation source: micro-focus sealed X-ray tube	5661 reflections with I > 2σ(I)
Detector resolution: 5.1996 pixels mm^-1	R_int = 0.017
ω scans	θ_max = 74.5°, θ_min = 6.7°
Absorption correction: multi-scan CrysAlisPro 1.171.38.34a (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −16→16
T_min = 0.686, T_max = 1.000	k = −16→16
17521 measured reflections	l = −21→21

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.054	w = 1/[σ²(F_o²) + (0.1113P)² + 0.3512P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.166	(Δ/σ)_max = 0.001
S = 1.05	Δρ_max = 0.35 e Å⁻³
5936 reflections	Δρ_min = −0.30 e Å⁻³
355 parameters	Absolute structure: Flack x determined using 2272 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
13 restraints	Absolute structure parameter: 0.01 (7)
Primary atom site location: structure-invariant direct methods

Special details top

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O3	0.6247 (2)	−0.2465 (2)	0.77448 (19)	0.0876 (8)
H3	0.563268	−0.256102	0.775910	0.131*
O11	0.60620 (18)	0.2501 (2)	0.72204 (17)	0.0834 (8)
C1	0.60509 (19)	0.0285 (2)	0.71977 (18)	0.0589 (6)
H1A	0.563390	0.082182	0.740889	0.071*
H1B	0.586405	0.019409	0.665733	0.071*
C2	0.5834 (2)	−0.0688 (3)	0.7640 (2)	0.0661 (8)
H2A	0.598982	−0.059113	0.818517	0.079*
H2B	0.511934	−0.085149	0.759625	0.079*
C3	0.6454 (2)	−0.1547 (2)	0.7328 (2)	0.0657 (7)
H3A	0.625360	−0.165273	0.678599	0.079*
C4	0.7608 (2)	−0.1369 (2)	0.73424 (18)	0.0592 (6)
C5	0.78236 (18)	−0.03170 (19)	0.69640 (14)	0.0482 (5)
H5	0.763281	−0.040317	0.641799	0.058*
C6	0.89465 (19)	−0.0034 (2)	0.69381 (17)	0.0555 (6)
H6A	0.915934	0.020388	0.744524	0.067*
H6B	0.934554	−0.062670	0.681050	0.067*
C7	0.91369 (18)	0.0787 (2)	0.63346 (17)	0.0560 (6)
H7A	0.898827	0.051623	0.582382	0.067*
H7B	0.985071	0.096510	0.634491	0.067*
C8	0.85050 (16)	0.1754 (2)	0.64547 (14)	0.0466 (5)
C9	0.73734 (16)	0.14644 (18)	0.66393 (13)	0.0444 (5)
H9	0.711194	0.119332	0.614901	0.053*
C10	0.71825 (17)	0.0601 (2)	0.72444 (14)	0.0473 (5)
C11	0.6774 (2)	0.2433 (2)	0.67652 (17)	0.0563 (6)
C12	0.7055 (2)	0.3298 (2)	0.62902 (18)	0.0592 (6)
H12	0.666234	0.387871	0.633707	0.071*
C13	0.78376 (19)	0.33251 (19)	0.57892 (15)	0.0498 (5)
C14	0.85132 (17)	0.24051 (18)	0.56813 (14)	0.0462 (5)
C15	0.96153 (19)	0.2710 (2)	0.54663 (18)	0.0588 (6)
H15A	0.998106	0.286347	0.594068	0.071*
H15B	0.994607	0.213587	0.522508	0.071*
C16	0.9699 (2)	0.3619 (3)	0.4917 (2)	0.0658 (7)
H16A	1.040893	0.379028	0.485057	0.079*
H16B	0.943035	0.343220	0.441272	0.079*
C17	0.9128 (2)	0.4546 (2)	0.5216 (2)	0.0663 (7)
C18	0.7997 (2)	0.4271 (2)	0.53009 (18)	0.0559 (6)
H18	0.767354	0.482872	0.558057	0.067*
C19	0.7452 (2)	0.4179 (2)	0.45131 (18)	0.0580 (6)
H19A	0.673872	0.404068	0.460236	0.070*
H19B	0.773461	0.361381	0.422787	0.070*
C20	0.7553 (3)	0.5148 (2)	0.40163 (19)	0.0693 (8)
C21	0.8687 (3)	0.5344 (3)	0.3892 (2)	0.0795 (10)
H21A	0.897671	0.479291	0.359487	0.095*
H21B	0.877251	0.595987	0.359339	0.095*
C22	0.9252 (3)	0.5444 (3)	0.4664 (3)	0.0822 (10)
H22A	0.901546	0.604822	0.492565	0.099*
H22B	0.996886	0.553380	0.455588	0.099*
C23	0.8036 (3)	−0.1464 (3)	0.8162 (2)	0.0753 (9)
H23A	0.875325	−0.133657	0.815143	0.113*
H23B	0.791459	−0.213337	0.835393	0.113*
H23C	0.771114	−0.098188	0.849507	0.113*
C24	0.8096 (3)	−0.2199 (3)	0.6844 (3)	0.0805 (10)
H24A	0.788287	−0.284845	0.702890	0.121*
H24B	0.882139	−0.214833	0.687831	0.121*
H24C	0.788959	−0.211735	0.631303	0.121*
C25	0.7419 (2)	0.0940 (3)	0.80852 (16)	0.0634 (7)
H25A	0.813652	0.089933	0.817536	0.095*
H25B	0.707081	0.050723	0.844443	0.095*
H25C	0.719607	0.162344	0.815753	0.095*
C26	0.8965 (2)	0.2346 (3)	0.71383 (17)	0.0637 (7)
H26A	0.956910	0.268531	0.696921	0.096*
H26B	0.912927	0.188754	0.755131	0.096*
H26C	0.848235	0.283438	0.732092	0.096*
C27	0.8078 (2)	0.1826 (2)	0.49730 (15)	0.0546 (6)
H27A	0.825358	0.217674	0.450395	0.082*
H27B	0.735333	0.178550	0.501716	0.082*
H27C	0.835850	0.115735	0.495938	0.082*
C28	0.9539 (3)	0.4887 (3)	0.6016 (3)	0.0879 (11)
H28A	0.914593	0.544709	0.620154	0.132*
H28B	1.023565	0.508645	0.596468	0.132*
H28C	0.948951	0.433751	0.637784	0.132*
C29	0.7052 (3)	0.4964 (3)	0.3217 (2)	0.0865 (11)
H29A	0.719916	0.552144	0.287825	0.130*
H29B	0.633132	0.490377	0.328046	0.130*
H29C	0.731577	0.435343	0.299453	0.130*
O30	0.6167 (15)	0.5742 (13)	0.4780 (14)	0.0842 (11)	0.325 (6)
O31	0.7073 (12)	0.6855 (9)	0.4071 (12)	0.109 (2)	0.325 (6)
C30	0.6878 (8)	0.5999 (6)	0.4258 (9)	0.0684 (16)	0.325 (6)
C31	0.5519 (9)	0.6585 (13)	0.4992 (8)	0.0770 (15)	0.325 (6)
H31	0.554804	0.708346	0.457219	0.092*	0.325 (6)
C32	0.6047 (15)	0.7018 (17)	0.5683 (10)	0.142 (3)*	0.325 (6)
H32A	0.591581	0.660334	0.612910	0.213*	0.325 (6)
H32B	0.580141	0.768903	0.577750	0.213*	0.325 (6)
H32C	0.676441	0.704018	0.558691	0.213*	0.325 (6)
C33	0.4432 (10)	0.6314 (16)	0.5122 (13)	0.131 (3)*	0.325 (6)
H33A	0.410009	0.622627	0.463073	0.196*	0.325 (6)
H33B	0.410361	0.684530	0.540664	0.196*	0.325 (6)
H33C	0.439334	0.569753	0.541367	0.196*	0.325 (6)
O30'	0.6259 (7)	0.5834 (6)	0.4788 (7)	0.0842 (11)	0.675 (6)
O31'	0.7423 (5)	0.6917 (4)	0.4401 (5)	0.109 (2)	0.675 (6)
C30'	0.7136 (4)	0.6052 (3)	0.4428 (3)	0.0684 (16)	0.675 (6)
C31'	0.5735 (5)	0.6593 (6)	0.5246 (3)	0.0770 (15)	0.675 (6)
H31'	0.618630	0.717622	0.530714	0.092*	0.675 (6)
C32'	0.5464 (9)	0.6211 (9)	0.6036 (4)	0.142 (3)*	0.675 (6)
H32D	0.606723	0.598698	0.629704	0.213*	0.675 (6)
H32E	0.499903	0.565691	0.598752	0.213*	0.675 (6)
H32F	0.515298	0.674275	0.632987	0.213*	0.675 (6)
C33'	0.4884 (7)	0.6887 (8)	0.4721 (5)	0.131 (3)*	0.675 (6)
H33D	0.447744	0.630370	0.460728	0.196*	0.675 (6)
H33E	0.515434	0.715632	0.424650	0.196*	0.675 (6)
H33F	0.447234	0.738883	0.497059	0.196*	0.675 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O3	0.0722 (14)	0.0701 (14)	0.121 (2)	−0.0093 (12)	0.0133 (15)	0.0293 (14)
O11	0.0696 (14)	0.0763 (14)	0.1042 (17)	0.0243 (12)	0.0405 (13)	0.0195 (13)
C1	0.0386 (11)	0.0687 (16)	0.0694 (15)	−0.0004 (11)	0.0034 (10)	0.0131 (13)
C2	0.0434 (12)	0.0800 (19)	0.0748 (17)	−0.0056 (12)	0.0099 (12)	0.0202 (15)
C3	0.0587 (15)	0.0654 (17)	0.0731 (16)	−0.0097 (13)	0.0025 (13)	0.0155 (14)
C4	0.0500 (13)	0.0587 (14)	0.0689 (15)	0.0028 (12)	0.0066 (12)	0.0170 (12)
C5	0.0414 (11)	0.0541 (12)	0.0493 (11)	0.0028 (9)	0.0009 (9)	0.0078 (10)
C6	0.0396 (11)	0.0615 (14)	0.0655 (14)	0.0083 (11)	0.0015 (10)	0.0122 (12)
C7	0.0357 (11)	0.0642 (15)	0.0680 (15)	0.0080 (10)	0.0095 (10)	0.0137 (13)
C8	0.0353 (10)	0.0552 (12)	0.0493 (11)	0.0007 (9)	0.0007 (8)	0.0025 (10)
C9	0.0366 (10)	0.0494 (11)	0.0473 (10)	0.0019 (9)	0.0023 (8)	0.0019 (9)
C10	0.0369 (10)	0.0553 (13)	0.0498 (11)	0.0017 (9)	0.0038 (9)	0.0059 (10)
C11	0.0460 (12)	0.0584 (14)	0.0645 (15)	0.0080 (11)	0.0137 (11)	0.0032 (12)
C12	0.0559 (14)	0.0517 (13)	0.0699 (15)	0.0116 (11)	0.0123 (12)	0.0021 (12)
C13	0.0449 (11)	0.0482 (12)	0.0564 (12)	−0.0014 (9)	0.0025 (9)	0.0009 (10)
C14	0.0391 (11)	0.0488 (11)	0.0505 (11)	−0.0008 (9)	0.0031 (9)	0.0012 (10)
C15	0.0405 (11)	0.0659 (15)	0.0701 (16)	−0.0015 (11)	0.0081 (11)	0.0082 (13)
C16	0.0477 (13)	0.0709 (17)	0.0789 (18)	−0.0070 (13)	0.0086 (13)	0.0143 (15)
C17	0.0574 (15)	0.0596 (15)	0.0819 (19)	−0.0136 (12)	−0.0002 (14)	0.0076 (14)
C18	0.0529 (13)	0.0468 (12)	0.0680 (15)	0.0003 (11)	0.0079 (11)	0.0042 (11)
C19	0.0526 (13)	0.0497 (12)	0.0717 (15)	−0.0002 (11)	0.0037 (12)	0.0125 (12)
C20	0.0644 (16)	0.0623 (16)	0.0811 (19)	0.0040 (14)	0.0119 (15)	0.0254 (15)
C21	0.0707 (19)	0.0721 (19)	0.096 (2)	−0.0073 (15)	0.0190 (18)	0.0299 (18)
C22	0.075 (2)	0.0645 (18)	0.107 (3)	−0.0196 (15)	0.005 (2)	0.0198 (18)
C23	0.0610 (16)	0.087 (2)	0.0775 (19)	0.0056 (16)	0.0006 (14)	0.0373 (18)
C24	0.080 (2)	0.0578 (16)	0.103 (3)	0.0085 (15)	0.020 (2)	0.0119 (17)
C25	0.0639 (16)	0.0758 (17)	0.0506 (13)	−0.0023 (14)	0.0070 (12)	0.0016 (12)
C26	0.0580 (15)	0.0733 (17)	0.0599 (15)	−0.0124 (14)	−0.0083 (12)	0.0022 (13)
C27	0.0606 (14)	0.0542 (12)	0.0490 (12)	−0.0005 (11)	0.0014 (11)	−0.0015 (10)
C28	0.086 (2)	0.078 (2)	0.100 (3)	−0.0279 (19)	−0.011 (2)	−0.003 (2)
C29	0.078 (2)	0.093 (2)	0.088 (2)	0.006 (2)	0.0020 (18)	0.036 (2)
O30	0.088 (2)	0.0503 (18)	0.114 (2)	0.0024 (16)	0.0309 (19)	0.0050 (16)
O31	0.099 (5)	0.0522 (15)	0.176 (8)	−0.012 (2)	0.016 (4)	0.012 (3)
C30	0.059 (3)	0.0557 (17)	0.090 (4)	−0.0077 (19)	−0.011 (3)	0.0202 (19)
C31	0.086 (3)	0.069 (2)	0.077 (4)	0.010 (3)	−0.023 (3)	−0.018 (3)
O30'	0.088 (2)	0.0503 (18)	0.114 (2)	0.0024 (16)	0.0309 (19)	0.0050 (16)
O31'	0.099 (5)	0.0522 (15)	0.176 (8)	−0.012 (2)	0.016 (4)	0.012 (3)
C30'	0.059 (3)	0.0557 (17)	0.090 (4)	−0.0077 (19)	−0.011 (3)	0.0202 (19)
C31'	0.086 (3)	0.069 (2)	0.077 (4)	0.010 (3)	−0.023 (3)	−0.018 (3)

Geometric parameters (Å, º) top

O3—H3	0.8200	C20—C29	1.546 (6)
O3—C3	1.438 (4)	C20—C30	1.4945 (14)
O11—C11	1.226 (3)	C20—C30'	1.4962 (14)
C1—H1A	0.9700	C21—H21A	0.9700
C1—H1B	0.9700	C21—H21B	0.9700
C1—C2	1.523 (4)	C21—C22	1.530 (6)
C1—C10	1.551 (3)	C22—H22A	0.9700
C2—H2A	0.9700	C22—H22B	0.9700
C2—H2B	0.9700	C23—H23A	0.9600
C2—C3	1.499 (5)	C23—H23B	0.9600
C3—H3A	0.9800	C23—H23C	0.9600
C3—C4	1.540 (4)	C24—H24A	0.9600
C4—C5	1.565 (4)	C24—H24B	0.9600
C4—C23	1.525 (5)	C24—H24C	0.9600
C4—C24	1.535 (5)	C25—H25A	0.9600
C5—H5	0.9800	C25—H25B	0.9600
C5—C6	1.527 (3)	C25—H25C	0.9600
C5—C10	1.557 (3)	C26—H26A	0.9600
C6—H6A	0.9700	C26—H26B	0.9600
C6—H6B	0.9700	C26—H26C	0.9600
C6—C7	1.526 (4)	C27—H27A	0.9600
C7—H7A	0.9700	C27—H27B	0.9600
C7—H7B	0.9700	C27—H27C	0.9600
C7—C8	1.541 (3)	C28—H28A	0.9600
C8—C9	1.573 (3)	C28—H28B	0.9600
C8—C14	1.587 (3)	C28—H28C	0.9600
C8—C26	1.539 (4)	C29—H29A	0.9600
C9—H9	0.9800	C29—H29B	0.9600
C9—C10	1.568 (3)	C29—H29C	0.9600
C9—C11	1.522 (3)	O30—C30	1.3430 (14)
C10—C25	1.548 (4)	O30—C31	1.4520 (14)
C11—C12	1.457 (4)	O31—C30	1.2069 (14)
C12—H12	0.9300	C31—H31	0.9800
C12—C13	1.345 (4)	C31—C32	1.4938 (14)
C13—C14	1.521 (3)	C31—C33	1.4939 (14)
C13—C18	1.523 (3)	C32—H32A	0.9600
C14—C15	1.552 (3)	C32—H32B	0.9600
C14—C27	1.551 (3)	C32—H32C	0.9600
C15—H15A	0.9700	C33—H33A	0.9600
C15—H15B	0.9700	C33—H33B	0.9600
C15—C16	1.535 (4)	C33—H33C	0.9600
C16—H16A	0.9700	O30'—C30'	1.3430 (14)
C16—H16B	0.9700	O30'—C31'	1.4521 (14)
C16—C17	1.529 (5)	O31'—C30'	1.2076 (13)
C17—C18	1.542 (4)	C31'—H31'	0.9800
C17—C22	1.532 (4)	C31'—C32'	1.4938 (14)
C17—C28	1.547 (5)	C31'—C33'	1.4935 (14)
C18—H18	0.9800	C32'—H32D	0.9600
C18—C19	1.540 (4)	C32'—H32E	0.9600
C19—H19A	0.9700	C32'—H32F	0.9600
C19—H19B	0.9700	C33'—H33D	0.9600
C19—C20	1.548 (4)	C33'—H33E	0.9600
C20—C21	1.532 (5)	C33'—H33F	0.9600

C3—O3—H3	109.5	C21—C20—C29	108.5 (3)
H1A—C1—H1B	107.8	C29—C20—C19	109.0 (3)
C2—C1—H1A	109.1	C30—C20—C19	114.9 (6)
C2—C1—H1B	109.1	C30—C20—C21	119.4 (5)
C2—C1—C10	112.5 (2)	C30—C20—C29	96.5 (7)
C10—C1—H1A	109.1	C30'—C20—C19	111.7 (3)
C10—C1—H1B	109.1	C30'—C20—C21	106.8 (3)
C1—C2—H2A	109.4	C30'—C20—C29	113.1 (4)
C1—C2—H2B	109.4	C20—C21—H21A	109.3
H2A—C2—H2B	108.0	C20—C21—H21B	109.3
C3—C2—C1	111.2 (2)	H21A—C21—H21B	108.0
C3—C2—H2A	109.4	C22—C21—C20	111.6 (3)
C3—C2—H2B	109.4	C22—C21—H21A	109.3
O3—C3—C2	111.1 (3)	C22—C21—H21B	109.3
O3—C3—H3A	107.6	C17—C22—H22A	108.6
O3—C3—C4	108.0 (2)	C17—C22—H22B	108.6
C2—C3—H3A	107.6	C21—C22—C17	114.8 (3)
C2—C3—C4	114.6 (3)	C21—C22—H22A	108.6
C4—C3—H3A	107.6	C21—C22—H22B	108.6
C3—C4—C5	108.0 (2)	H22A—C22—H22B	107.5
C23—C4—C3	111.6 (2)	C4—C23—H23A	109.5
C23—C4—C5	113.0 (3)	C4—C23—H23B	109.5
C23—C4—C24	107.6 (3)	C4—C23—H23C	109.5
C24—C4—C3	107.2 (3)	H23A—C23—H23B	109.5
C24—C4—C5	109.2 (2)	H23A—C23—H23C	109.5
C4—C5—H5	104.4	H23B—C23—H23C	109.5
C6—C5—C4	114.0 (2)	C4—C24—H24A	109.5
C6—C5—H5	104.4	C4—C24—H24B	109.5
C6—C5—C10	110.1 (2)	C4—C24—H24C	109.5
C10—C5—C4	117.9 (2)	H24A—C24—H24B	109.5
C10—C5—H5	104.4	H24A—C24—H24C	109.5
C5—C6—H6A	109.5	H24B—C24—H24C	109.5
C5—C6—H6B	109.5	C10—C25—H25A	109.5
H6A—C6—H6B	108.1	C10—C25—H25B	109.5
C7—C6—C5	110.8 (2)	C10—C25—H25C	109.5
C7—C6—H6A	109.5	H25A—C25—H25B	109.5
C7—C6—H6B	109.5	H25A—C25—H25C	109.5
C6—C7—H7A	108.7	H25B—C25—H25C	109.5
C6—C7—H7B	108.7	C8—C26—H26A	109.5
C6—C7—C8	114.3 (2)	C8—C26—H26B	109.5
H7A—C7—H7B	107.6	C8—C26—H26C	109.5
C8—C7—H7A	108.7	H26A—C26—H26B	109.5
C8—C7—H7B	108.7	H26A—C26—H26C	109.5
C7—C8—C9	109.7 (2)	H26B—C26—H26C	109.5
C7—C8—C14	109.59 (19)	C14—C27—H27A	109.5
C9—C8—C14	107.98 (17)	C14—C27—H27B	109.5
C26—C8—C7	108.3 (2)	C14—C27—H27C	109.5
C26—C8—C9	110.1 (2)	H27A—C27—H27B	109.5
C26—C8—C14	111.2 (2)	H27A—C27—H27C	109.5
C8—C9—H9	104.4	H27B—C27—H27C	109.5
C10—C9—C8	117.68 (18)	C17—C28—H28A	109.5
C10—C9—H9	104.4	C17—C28—H28B	109.5
C11—C9—C8	108.4 (2)	C17—C28—H28C	109.5
C11—C9—H9	104.4	H28A—C28—H28B	109.5
C11—C9—C10	115.89 (19)	H28A—C28—H28C	109.5
C1—C10—C5	107.1 (2)	H28B—C28—H28C	109.5
C1—C10—C9	108.48 (19)	C20—C29—H29A	109.5
C5—C10—C9	106.06 (18)	C20—C29—H29B	109.5
C25—C10—C1	108.7 (2)	C20—C29—H29C	109.5
C25—C10—C5	114.0 (2)	H29A—C29—H29B	109.5
C25—C10—C9	112.2 (2)	H29A—C29—H29C	109.5
O11—C11—C9	123.4 (3)	H29B—C29—H29C	109.5
O11—C11—C12	119.7 (3)	C30—O30—C31	112.6 (12)
C12—C11—C9	116.8 (2)	O30—C30—C20	114.2 (9)
C11—C12—H12	117.4	O31—C30—C20	120.5 (12)
C13—C12—C11	125.2 (2)	O31—C30—O30	124.4 (13)
C13—C12—H12	117.4	O30—C31—H31	108.1
C12—C13—C14	120.4 (2)	O30—C31—C32	102.8 (17)
C12—C13—C18	118.8 (2)	O30—C31—C33	114.7 (15)
C14—C13—C18	120.7 (2)	C32—C31—H31	108.1
C13—C14—C8	109.22 (19)	C32—C31—C33	114.8 (13)
C13—C14—C15	111.6 (2)	C33—C31—H31	108.1
C13—C14—C27	106.0 (2)	C31—C32—H32A	109.5
C15—C14—C8	110.36 (19)	C31—C32—H32B	109.5
C27—C14—C8	112.9 (2)	C31—C32—H32C	109.5
C27—C14—C15	106.7 (2)	H32A—C32—H32B	109.5
C14—C15—H15A	108.6	H32A—C32—H32C	109.5
C14—C15—H15B	108.6	H32B—C32—H32C	109.5
H15A—C15—H15B	107.6	C31—C33—H33A	109.5
C16—C15—C14	114.7 (2)	C31—C33—H33B	109.5
C16—C15—H15A	108.6	C31—C33—H33C	109.5
C16—C15—H15B	108.6	H33A—C33—H33B	109.5
C15—C16—H16A	109.0	H33A—C33—H33C	109.5
C15—C16—H16B	109.0	H33B—C33—H33C	109.5
H16A—C16—H16B	107.8	C30'—O30'—C31'	120.7 (6)
C17—C16—C15	112.8 (3)	O30'—C30'—C20	111.3 (4)
C17—C16—H16A	109.0	O31'—C30'—C20	128.7 (6)
C17—C16—H16B	109.0	O31'—C30'—O30'	119.4 (6)
C16—C17—C18	108.5 (2)	O30'—C31'—H31'	108.4
C16—C17—C22	111.3 (3)	O30'—C31'—C32'	111.9 (7)
C16—C17—C28	111.2 (3)	O30'—C31'—C33'	102.0 (7)
C18—C17—C28	108.8 (3)	C32'—C31'—H31'	108.4
C22—C17—C18	110.2 (3)	C33'—C31'—H31'	108.4
C22—C17—C28	106.8 (3)	C33'—C31'—C32'	117.4 (8)
C13—C18—C17	112.4 (2)	C31'—C32'—H32D	109.5
C13—C18—H18	106.8	C31'—C32'—H32E	109.5
C13—C18—C19	110.9 (2)	C31'—C32'—H32F	109.5
C17—C18—H18	106.8	H32D—C32'—H32E	109.5
C19—C18—C17	112.7 (2)	H32D—C32'—H32F	109.5
C19—C18—H18	106.8	H32E—C32'—H32F	109.5
C18—C19—H19A	109.1	C31'—C33'—H33D	109.5
C18—C19—H19B	109.1	C31'—C33'—H33E	109.5
C18—C19—C20	112.4 (2)	C31'—C33'—H33F	109.5
H19A—C19—H19B	107.9	H33D—C33'—H33E	109.5
C20—C19—H19A	109.1	H33D—C33'—H33F	109.5
C20—C19—H19B	109.1	H33E—C33'—H33F	109.5
C21—C20—C19	107.6 (2)

O3—C3—C4—C5	−174.3 (3)	C14—C13—C18—C17	−42.9 (3)
O3—C3—C4—C23	−49.5 (4)	C14—C13—C18—C19	84.3 (3)
O3—C3—C4—C24	68.2 (3)	C14—C15—C16—C17	53.9 (4)
O11—C11—C12—C13	177.9 (3)	C15—C16—C17—C18	−60.0 (4)
C1—C2—C3—O3	−179.9 (3)	C15—C16—C17—C22	178.5 (3)
C1—C2—C3—C4	57.4 (4)	C15—C16—C17—C28	59.6 (3)
C2—C1—C10—C5	54.2 (3)	C16—C17—C18—C13	53.0 (3)
C2—C1—C10—C9	168.3 (2)	C16—C17—C18—C19	−73.2 (3)
C2—C1—C10—C25	−69.5 (3)	C16—C17—C22—C21	71.1 (4)
C2—C3—C4—C5	−49.9 (3)	C17—C18—C19—C20	−55.8 (3)
C2—C3—C4—C23	74.9 (3)	C18—C13—C14—C8	156.3 (2)
C2—C3—C4—C24	−167.5 (3)	C18—C13—C14—C15	34.0 (3)
C3—C4—C5—C6	179.9 (3)	C18—C13—C14—C27	−81.8 (3)
C3—C4—C5—C10	48.5 (3)	C18—C17—C22—C21	−49.4 (4)
C4—C5—C6—C7	160.4 (2)	C18—C19—C20—C21	58.5 (3)
C4—C5—C10—C1	−51.0 (3)	C18—C19—C20—C29	176.0 (3)
C4—C5—C10—C9	−166.7 (2)	C18—C19—C20—C30	−77.1 (7)
C4—C5—C10—C25	69.3 (3)	C18—C19—C20—C30'	−58.4 (4)
C5—C6—C7—C8	56.5 (3)	C19—C20—C21—C22	−57.4 (4)
C6—C5—C10—C1	175.9 (2)	C19—C20—C30—O30	−10.9 (19)
C6—C5—C10—C9	60.2 (2)	C19—C20—C30—O31	159.4 (14)
C6—C5—C10—C25	−63.8 (3)	C19—C20—C30'—O30'	−42.2 (8)
C6—C7—C8—C9	−45.0 (3)	C19—C20—C30'—O31'	146.4 (6)
C6—C7—C8—C14	−163.4 (2)	C20—C21—C22—C17	55.5 (4)
C6—C7—C8—C26	75.1 (3)	C21—C20—C30—O30	−140.9 (16)
C7—C8—C9—C10	45.3 (3)	C21—C20—C30—O31	29.3 (19)
C7—C8—C9—C11	179.3 (2)	C21—C20—C30'—O30'	−159.6 (7)
C7—C8—C14—C13	176.7 (2)	C21—C20—C30'—O31'	29.0 (7)
C7—C8—C14—C15	−60.3 (3)	C22—C17—C18—C13	175.1 (3)
C7—C8—C14—C27	59.0 (3)	C22—C17—C18—C19	48.9 (4)
C8—C9—C10—C1	−167.5 (2)	C23—C4—C5—C6	55.9 (3)
C8—C9—C10—C5	−52.7 (3)	C23—C4—C5—C10	−75.4 (3)
C8—C9—C10—C25	72.4 (3)	C24—C4—C5—C6	−63.8 (3)
C8—C9—C11—O11	−146.9 (3)	C24—C4—C5—C10	164.8 (3)
C8—C9—C11—C12	35.5 (3)	C26—C8—C9—C10	−73.7 (3)
C8—C14—C15—C16	−159.7 (2)	C26—C8—C9—C11	60.2 (3)
C9—C8—C14—C13	57.2 (2)	C26—C8—C14—C13	−63.7 (3)
C9—C8—C14—C15	−179.7 (2)	C26—C8—C14—C15	59.4 (3)
C9—C8—C14—C27	−60.4 (3)	C26—C8—C14—C27	178.7 (2)
C9—C11—C12—C13	−4.4 (5)	C27—C14—C15—C16	77.4 (3)
C10—C1—C2—C3	−59.4 (4)	C28—C17—C18—C13	−68.1 (3)
C10—C5—C6—C7	−64.5 (3)	C28—C17—C18—C19	165.6 (3)
C10—C9—C11—O11	−11.9 (4)	C28—C17—C22—C21	−167.4 (4)
C10—C9—C11—C12	170.4 (2)	C29—C20—C21—C22	−175.1 (3)
C11—C9—C10—C1	61.8 (3)	C29—C20—C30—O30	103.5 (17)
C11—C9—C10—C5	176.6 (2)	C29—C20—C30—O31	−86.2 (16)
C11—C9—C10—C25	−58.3 (3)	C29—C20—C30'—O30'	81.1 (7)
C11—C12—C13—C14	0.0 (5)	C29—C20—C30'—O31'	−90.3 (7)
C11—C12—C13—C18	176.6 (3)	C30—C20—C21—C22	75.8 (8)
C12—C13—C14—C8	−27.2 (3)	C30—O30—C31—C32	−92 (2)
C12—C13—C14—C15	−149.5 (3)	C30—O30—C31—C33	143.1 (19)
C12—C13—C14—C27	94.7 (3)	C31—O30—C30—C20	−179.2 (15)
C12—C13—C18—C17	140.5 (3)	C31—O30—C30—O31	11 (3)
C12—C13—C18—C19	−92.3 (3)	C30'—C20—C21—C22	62.7 (4)
C13—C14—C15—C16	−38.0 (3)	C30'—O30'—C31'—C32'	−129.6 (10)
C13—C18—C19—C20	177.2 (2)	C30'—O30'—C31'—C33'	104.1 (11)
C14—C8—C9—C10	164.6 (2)	C31'—O30'—C30'—C20	178.0 (8)
C14—C8—C9—C11	−61.4 (2)	C31'—O30'—C30'—O31'	−9.7 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O11ⁱ	0.82	2.24	3.044 (4)	169

Symmetry code: (i) −x+1, y−1/2, −z+3/2.

(18b_et) top

Crystal data top

C₃₂H₅₀O₄	D_x = 1.173 Mg m⁻³
M_r = 498.72	Melting point: 495-497 K
Orthorhombic, P2₁2₁2₁	Cu Kα radiation, λ = 1.54184 Å
a = 13.02432 (14) Å	Cell parameters from 15860 reflections
b = 12.99238 (13) Å	θ = 2.6–76.4°
c = 16.69407 (19) Å	µ = 0.58 mm⁻¹
V = 2824.92 (5) Å³	T = 298 K
Z = 4	Plate, colorless
F(000) = 1096	0.6 × 0.2 × 0.15 mm

Data collection top

SuperNova, Dual, Cu at home/near, Atlas diffractometer	5167 independent reflections
Radiation source: micro-focus sealed X-ray tube	4966 reflections with I > 2σ(I)
Detector resolution: 10.3991 pixels mm^-1	R_int = 0.033
ω scans	θ_max = 68.3°, θ_min = 6.8°
Absorption correction: multi-scan CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −15→15
T_min = 0.880, T_max = 1.000	k = −15→14
27501 measured reflections	l = −20→19

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.039	w = 1/[σ²(F_o²) + (0.062P)² + 0.557P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.106	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.22 e Å⁻³
5167 reflections	Δρ_min = −0.26 e Å⁻³
335 parameters	Absolute structure: Flack x determined using 2119 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
2 restraints	Absolute structure parameter: −0.05 (7)

Special details top

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O3	0.62462 (17)	−0.26938 (15)	0.75553 (17)	0.0631 (6)
H3	0.562385	−0.278450	0.757855	0.095*
O11	0.61069 (15)	0.24152 (14)	0.72747 (13)	0.0516 (5)
O30	0.61090 (15)	0.59397 (14)	0.47485 (13)	0.0503 (5)
O31	0.7248 (2)	0.70721 (16)	0.4301 (2)	0.0877 (9)
C1	0.60682 (16)	0.01596 (18)	0.71606 (15)	0.0349 (5)
H1A	0.567131	0.069253	0.742466	0.042*
H1B	0.583842	0.011924	0.660881	0.042*
C2	0.58624 (18)	−0.08648 (19)	0.75710 (16)	0.0397 (5)
H2A	0.605934	−0.081825	0.813018	0.048*
H2B	0.513375	−0.101640	0.754807	0.048*
C3	0.6454 (2)	−0.17240 (19)	0.71755 (17)	0.0421 (6)
H3A	0.621689	−0.177305	0.661969	0.051*
C4	0.76200 (18)	−0.15533 (17)	0.71563 (14)	0.0351 (5)
C5	0.78344 (16)	−0.04544 (16)	0.68096 (12)	0.0283 (4)
H5	0.761052	−0.049134	0.624992	0.034*
C6	0.89754 (16)	−0.01827 (18)	0.67656 (15)	0.0333 (5)
H6A	0.922038	0.000831	0.729379	0.040*
H6B	0.936210	−0.077867	0.658824	0.040*
C7	0.91481 (17)	0.07092 (17)	0.61842 (14)	0.0345 (5)
H7A	0.897685	0.048021	0.564751	0.041*
H7B	0.987122	0.088778	0.618786	0.041*
C8	0.85192 (15)	0.16789 (16)	0.63747 (13)	0.0272 (4)
C9	0.73849 (15)	0.13856 (15)	0.65844 (12)	0.0260 (4)
H9	0.709232	0.114940	0.607580	0.031*
C10	0.72133 (15)	0.04629 (15)	0.71743 (12)	0.0271 (4)
C11	0.67945 (16)	0.23675 (18)	0.67778 (14)	0.0318 (5)
C12	0.70604 (17)	0.32886 (17)	0.63144 (13)	0.0327 (5)
H12	0.666587	0.387585	0.639629	0.039*
C13	0.78270 (15)	0.33491 (16)	0.57828 (12)	0.0271 (4)
C14	0.85023 (15)	0.24125 (16)	0.56124 (13)	0.0277 (4)
C15	0.96142 (16)	0.27330 (18)	0.53805 (15)	0.0346 (5)
H15A	1.000430	0.284429	0.586775	0.042*
H15B	0.993330	0.216756	0.509413	0.042*
C16	0.96862 (17)	0.37037 (18)	0.48621 (15)	0.0366 (5)
H16A	1.040358	0.388367	0.479315	0.044*
H16B	0.940448	0.355579	0.433670	0.044*
C17	0.91163 (17)	0.46265 (17)	0.52199 (14)	0.0337 (5)
C18	0.79708 (17)	0.43403 (16)	0.53119 (13)	0.0300 (4)
H18	0.764838	0.489127	0.562412	0.036*
C19	0.74037 (17)	0.42921 (16)	0.45021 (14)	0.0329 (5)
H19A	0.766786	0.371429	0.419724	0.040*
H19B	0.668085	0.416570	0.460167	0.040*
C20	0.75090 (19)	0.52741 (17)	0.39946 (14)	0.0354 (5)
C21	0.86498 (19)	0.55179 (19)	0.38850 (16)	0.0411 (6)
H21A	0.896339	0.498567	0.355911	0.049*
H21B	0.871916	0.616638	0.360223	0.049*
C22	0.92137 (19)	0.55872 (19)	0.46789 (16)	0.0410 (5)
H22A	0.895520	0.617853	0.497077	0.049*
H22B	0.993570	0.570785	0.457182	0.049*
C23	0.8079 (2)	−0.2359 (2)	0.65843 (19)	0.0532 (7)
H23A	0.881469	−0.233651	0.661556	0.080*
H23B	0.786590	−0.221210	0.604589	0.080*
H23C	0.784306	−0.303208	0.673456	0.080*
C24	0.81011 (19)	−0.1717 (2)	0.79811 (15)	0.0428 (6)
H24A	0.882148	−0.156344	0.795645	0.064*
H24B	0.800778	−0.241982	0.814251	0.064*
H24C	0.777652	−0.126998	0.836269	0.064*
C25	0.75058 (18)	0.07335 (17)	0.80465 (13)	0.0345 (5)
H25A	0.713837	0.029229	0.840789	0.052*
H25B	0.732996	0.143779	0.815350	0.052*
H25C	0.823068	0.063857	0.811984	0.052*
C26	0.90257 (18)	0.2227 (2)	0.70952 (14)	0.0376 (5)
H26A	0.860341	0.279363	0.726112	0.056*
H26B	0.969045	0.247770	0.694155	0.056*
H26C	0.909791	0.174944	0.753053	0.056*
C27	0.8029 (2)	0.18754 (17)	0.48680 (13)	0.0363 (5)
H27A	0.729464	0.187112	0.491452	0.054*
H27B	0.827659	0.118056	0.483650	0.054*
H27C	0.822419	0.224261	0.439269	0.054*
C28	0.9565 (2)	0.4906 (2)	0.60431 (17)	0.0480 (6)
H28A	1.028562	0.504720	0.598932	0.072*
H28B	0.946855	0.434114	0.640589	0.072*
H28C	0.922243	0.550474	0.624818	0.072*
C29	0.7017 (2)	0.5093 (2)	0.31688 (16)	0.0480 (6)
H29A	0.629947	0.494671	0.323449	0.072*
H29B	0.734673	0.452088	0.291133	0.072*
H29C	0.709791	0.569836	0.284513	0.072*
C30	0.69644 (19)	0.61976 (18)	0.43636 (16)	0.0417 (5)
C31	0.5523 (2)	0.6784 (2)	0.5080 (2)	0.0631 (8)
H31A	0.528306	0.722638	0.465071	0.076*	0.52 (2)
H31B	0.595661	0.719051	0.543104	0.076*	0.52 (2)
H31C	0.502985	0.704189	0.469342	0.076*	0.48 (2)
H31D	0.597128	0.734362	0.524083	0.076*	0.48 (2)
C32	0.4607 (6)	0.6369 (5)	0.5550 (6)	0.060 (3)*	0.52 (2)
H32A	0.409793	0.611677	0.518321	0.090*	0.52 (2)
H32B	0.431756	0.691121	0.586892	0.090*	0.52 (2)
H32C	0.482925	0.581947	0.589226	0.090*	0.52 (2)
C32A	0.4976 (11)	0.6315 (7)	0.5809 (6)	0.074 (3)*	0.48 (2)
H32D	0.457310	0.573506	0.564153	0.111*	0.48 (2)
H32E	0.453532	0.682223	0.604783	0.111*	0.48 (2)
H32F	0.547719	0.609499	0.619457	0.111*	0.48 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O3	0.0503 (11)	0.0357 (10)	0.1034 (17)	−0.0098 (9)	0.0072 (12)	0.0181 (10)
O11	0.0467 (10)	0.0419 (10)	0.0662 (12)	0.0147 (8)	0.0299 (9)	0.0131 (8)
O30	0.0438 (10)	0.0410 (9)	0.0662 (12)	0.0036 (8)	0.0157 (9)	−0.0009 (9)
O31	0.0831 (17)	0.0343 (10)	0.146 (3)	0.0039 (11)	0.0484 (18)	0.0119 (13)
C1	0.0235 (10)	0.0356 (11)	0.0455 (12)	0.0001 (9)	−0.0007 (9)	0.0078 (10)
C2	0.0260 (10)	0.0414 (13)	0.0518 (14)	−0.0039 (9)	0.0018 (10)	0.0105 (11)
C3	0.0410 (13)	0.0320 (12)	0.0534 (14)	−0.0088 (10)	−0.0031 (11)	0.0067 (11)
C4	0.0350 (11)	0.0289 (10)	0.0415 (12)	0.0002 (9)	0.0030 (10)	0.0043 (9)
C5	0.0274 (10)	0.0283 (10)	0.0293 (10)	0.0018 (8)	0.0010 (8)	0.0035 (8)
C6	0.0259 (10)	0.0317 (11)	0.0424 (12)	0.0067 (9)	0.0052 (9)	0.0076 (9)
C7	0.0266 (10)	0.0326 (11)	0.0441 (12)	0.0073 (9)	0.0088 (9)	0.0085 (9)
C8	0.0205 (9)	0.0283 (10)	0.0329 (10)	0.0007 (8)	0.0012 (7)	0.0035 (8)
C9	0.0225 (9)	0.0276 (9)	0.0280 (9)	0.0008 (8)	0.0000 (7)	0.0011 (8)
C10	0.0225 (10)	0.0279 (10)	0.0307 (10)	0.0010 (8)	0.0011 (8)	0.0032 (8)
C11	0.0252 (10)	0.0333 (11)	0.0369 (11)	0.0047 (9)	0.0051 (9)	0.0028 (9)
C12	0.0306 (10)	0.0285 (10)	0.0391 (11)	0.0079 (9)	0.0049 (9)	0.0023 (9)
C13	0.0243 (9)	0.0280 (10)	0.0292 (9)	0.0010 (8)	−0.0016 (8)	0.0013 (8)
C14	0.0241 (9)	0.0276 (10)	0.0312 (10)	0.0015 (8)	0.0031 (8)	0.0020 (8)
C15	0.0249 (10)	0.0346 (11)	0.0443 (12)	0.0035 (9)	0.0077 (9)	0.0072 (10)
C16	0.0262 (10)	0.0371 (12)	0.0467 (13)	0.0005 (9)	0.0067 (9)	0.0094 (10)
C17	0.0279 (11)	0.0305 (11)	0.0425 (12)	−0.0039 (8)	−0.0015 (9)	0.0046 (9)
C18	0.0295 (10)	0.0254 (9)	0.0351 (11)	0.0024 (8)	0.0017 (9)	0.0033 (8)
C19	0.0291 (10)	0.0313 (10)	0.0384 (11)	0.0006 (9)	−0.0010 (9)	0.0070 (9)
C20	0.0337 (11)	0.0346 (11)	0.0380 (11)	0.0023 (10)	0.0023 (9)	0.0095 (9)
C21	0.0375 (12)	0.0377 (12)	0.0482 (13)	0.0014 (10)	0.0071 (10)	0.0162 (10)
C22	0.0351 (11)	0.0331 (11)	0.0547 (14)	−0.0052 (10)	0.0042 (11)	0.0095 (10)
C23	0.0649 (17)	0.0301 (12)	0.0645 (17)	0.0032 (12)	0.0165 (14)	−0.0009 (11)
C24	0.0387 (12)	0.0412 (13)	0.0486 (14)	0.0041 (10)	0.0026 (11)	0.0172 (11)
C25	0.0360 (11)	0.0363 (11)	0.0313 (11)	0.0002 (10)	0.0024 (9)	0.0020 (9)
C26	0.0327 (11)	0.0423 (12)	0.0379 (12)	−0.0067 (10)	−0.0080 (9)	0.0045 (10)
C27	0.0464 (13)	0.0316 (11)	0.0308 (10)	−0.0003 (10)	−0.0006 (10)	−0.0014 (8)
C28	0.0457 (14)	0.0453 (14)	0.0530 (15)	−0.0070 (11)	−0.0114 (12)	−0.0005 (11)
C29	0.0486 (14)	0.0561 (16)	0.0393 (13)	0.0031 (13)	−0.0031 (11)	0.0146 (11)
C30	0.0403 (12)	0.0341 (12)	0.0508 (14)	0.0045 (10)	0.0050 (11)	0.0115 (10)
C31	0.0583 (18)	0.0572 (17)	0.074 (2)	0.0155 (15)	0.0110 (15)	−0.0116 (16)

Geometric parameters (Å, º) top

O3—H3	0.8200	C17—C22	1.546 (3)
O3—C3	1.436 (3)	C17—C28	1.537 (3)
O11—C11	1.222 (3)	C18—H18	0.9800
O30—C30	1.329 (3)	C18—C19	1.542 (3)
O30—C31	1.447 (3)	C19—H19A	0.9700
O31—C30	1.199 (3)	C19—H19B	0.9700
C1—H1A	0.9700	C19—C20	1.538 (3)
C1—H1B	0.9700	C20—C21	1.530 (3)
C1—C2	1.521 (3)	C20—C29	1.538 (4)
C1—C10	1.543 (3)	C20—C30	1.524 (3)
C2—H2A	0.9700	C21—H21A	0.9700
C2—H2B	0.9700	C21—H21B	0.9700
C2—C3	1.509 (4)	C21—C22	1.518 (4)
C3—H3A	0.9800	C22—H22A	0.9700
C3—C4	1.535 (3)	C22—H22B	0.9700
C4—C5	1.566 (3)	C23—H23A	0.9600
C4—C23	1.538 (3)	C23—H23B	0.9600
C4—C24	1.528 (3)	C23—H23C	0.9600
C5—H5	0.9800	C24—H24A	0.9600
C5—C6	1.529 (3)	C24—H24B	0.9600
C5—C10	1.564 (3)	C24—H24C	0.9600
C6—H6A	0.9700	C25—H25A	0.9600
C6—H6B	0.9700	C25—H25B	0.9600
C6—C7	1.528 (3)	C25—H25C	0.9600
C7—H7A	0.9700	C26—H26A	0.9600
C7—H7B	0.9700	C26—H26B	0.9600
C7—C8	1.536 (3)	C26—H26C	0.9600
C8—C9	1.565 (3)	C27—H27A	0.9600
C8—C14	1.590 (3)	C27—H27B	0.9600
C8—C26	1.546 (3)	C27—H27C	0.9600
C9—H9	0.9800	C28—H28A	0.9600
C9—C10	1.567 (3)	C28—H28B	0.9600
C9—C11	1.524 (3)	C28—H28C	0.9600
C10—C25	1.546 (3)	C29—H29A	0.9600
C11—C12	1.466 (3)	C29—H29B	0.9600
C12—H12	0.9300	C29—H29C	0.9600
C12—C13	1.338 (3)	C31—H31A	0.9700
C13—C14	1.528 (3)	C31—H31B	0.9700
C13—C18	1.520 (3)	C31—H31C	0.9700
C14—C15	1.556 (3)	C31—H31D	0.9700
C14—C27	1.553 (3)	C31—C32	1.526 (3)
C15—H15A	0.9700	C31—C32A	1.537 (3)
C15—H15B	0.9700	C32—H32A	0.9600
C15—C16	1.532 (3)	C32—H32B	0.9600
C16—H16A	0.9700	C32—H32C	0.9600
C16—H16B	0.9700	C32A—H32D	0.9600
C16—C17	1.531 (3)	C32A—H32E	0.9600
C17—C18	1.545 (3)	C32A—H32F	0.9600

C3—O3—H3	109.5	C13—C18—C19	111.10 (17)
C30—O30—C31	115.8 (2)	C17—C18—H18	106.9
H1A—C1—H1B	107.8	C19—C18—C17	112.66 (18)
C2—C1—H1A	109.0	C19—C18—H18	106.9
C2—C1—H1B	109.0	C18—C19—H19A	108.8
C2—C1—C10	112.78 (18)	C18—C19—H19B	108.8
C10—C1—H1A	109.0	H19A—C19—H19B	107.6
C10—C1—H1B	109.0	C20—C19—C18	113.99 (18)
C1—C2—H2A	109.4	C20—C19—H19A	108.8
C1—C2—H2B	109.4	C20—C19—H19B	108.8
H2A—C2—H2B	108.0	C19—C20—C29	109.2 (2)
C3—C2—C1	111.1 (2)	C21—C20—C19	108.92 (18)
C3—C2—H2A	109.4	C21—C20—C29	109.2 (2)
C3—C2—H2B	109.4	C30—C20—C19	112.90 (19)
O3—C3—C2	111.1 (2)	C30—C20—C21	109.7 (2)
O3—C3—H3A	107.5	C30—C20—C29	106.8 (2)
O3—C3—C4	108.8 (2)	C20—C21—H21A	109.2
C2—C3—H3A	107.5	C20—C21—H21B	109.2
C2—C3—C4	114.1 (2)	H21A—C21—H21B	107.9
C4—C3—H3A	107.5	C22—C21—C20	112.2 (2)
C3—C4—C5	108.41 (18)	C22—C21—H21A	109.2
C3—C4—C23	107.4 (2)	C22—C21—H21B	109.2
C23—C4—C5	108.79 (19)	C17—C22—H22A	108.5
C24—C4—C3	111.5 (2)	C17—C22—H22B	108.5
C24—C4—C5	112.76 (19)	C21—C22—C17	115.0 (2)
C24—C4—C23	107.8 (2)	C21—C22—H22A	108.5
C4—C5—H5	104.8	C21—C22—H22B	108.5
C6—C5—C4	113.67 (17)	H22A—C22—H22B	107.5
C6—C5—H5	104.8	C4—C23—H23A	109.5
C6—C5—C10	110.22 (17)	C4—C23—H23B	109.5
C10—C5—C4	117.31 (17)	C4—C23—H23C	109.5
C10—C5—H5	104.8	H23A—C23—H23B	109.5
C5—C6—H6A	109.6	H23A—C23—H23C	109.5
C5—C6—H6B	109.6	H23B—C23—H23C	109.5
H6A—C6—H6B	108.1	C4—C24—H24A	109.5
C7—C6—C5	110.40 (17)	C4—C24—H24B	109.5
C7—C6—H6A	109.6	C4—C24—H24C	109.5
C7—C6—H6B	109.6	H24A—C24—H24B	109.5
C6—C7—H7A	108.7	H24A—C24—H24C	109.5
C6—C7—H7B	108.7	H24B—C24—H24C	109.5
C6—C7—C8	114.33 (18)	C10—C25—H25A	109.5
H7A—C7—H7B	107.6	C10—C25—H25B	109.5
C8—C7—H7A	108.7	C10—C25—H25C	109.5
C8—C7—H7B	108.7	H25A—C25—H25B	109.5
C7—C8—C9	110.48 (17)	H25A—C25—H25C	109.5
C7—C8—C14	109.47 (17)	H25B—C25—H25C	109.5
C7—C8—C26	108.14 (18)	C8—C26—H26A	109.5
C9—C8—C14	108.17 (15)	C8—C26—H26B	109.5
C26—C8—C9	109.93 (17)	C8—C26—H26C	109.5
C26—C8—C14	110.65 (17)	H26A—C26—H26B	109.5
C8—C9—H9	104.4	H26A—C26—H26C	109.5
C8—C9—C10	117.47 (16)	H26B—C26—H26C	109.5
C10—C9—H9	104.4	C14—C27—H27A	109.5
C11—C9—C8	108.65 (16)	C14—C27—H27B	109.5
C11—C9—H9	104.4	C14—C27—H27C	109.5
C11—C9—C10	115.80 (17)	H27A—C27—H27B	109.5
C1—C10—C5	107.44 (17)	H27A—C27—H27C	109.5
C1—C10—C9	108.90 (16)	H27B—C27—H27C	109.5
C1—C10—C25	108.08 (17)	C17—C28—H28A	109.5
C5—C10—C9	105.34 (15)	C17—C28—H28B	109.5
C25—C10—C5	114.37 (16)	C17—C28—H28C	109.5
C25—C10—C9	112.50 (17)	H28A—C28—H28B	109.5
O11—C11—C9	123.8 (2)	H28A—C28—H28C	109.5
O11—C11—C12	119.3 (2)	H28B—C28—H28C	109.5
C12—C11—C9	116.89 (17)	C20—C29—H29A	109.5
C11—C12—H12	117.5	C20—C29—H29B	109.5
C13—C12—C11	125.03 (19)	C20—C29—H29C	109.5
C13—C12—H12	117.5	H29A—C29—H29B	109.5
C12—C13—C14	120.40 (19)	H29A—C29—H29C	109.5
C12—C13—C18	118.98 (18)	H29B—C29—H29C	109.5
C18—C13—C14	120.49 (17)	O30—C30—C20	112.8 (2)
C13—C14—C8	109.65 (16)	O31—C30—O30	122.7 (3)
C13—C14—C15	111.65 (17)	O31—C30—C20	124.5 (2)
C13—C14—C27	106.17 (17)	O30—C31—H31A	109.7
C15—C14—C8	110.28 (16)	O30—C31—H31B	109.7
C27—C14—C8	112.13 (17)	O30—C31—H31C	110.9
C27—C14—C15	106.88 (18)	O30—C31—H31D	110.9
C14—C15—H15A	108.6	O30—C31—C32	109.9 (4)
C14—C15—H15B	108.6	O30—C31—C32A	104.3 (4)
H15A—C15—H15B	107.6	H31A—C31—H31B	108.2
C16—C15—C14	114.70 (18)	H31C—C31—H31D	108.9
C16—C15—H15A	108.6	C32—C31—H31A	109.7
C16—C15—H15B	108.6	C32—C31—H31B	109.7
C15—C16—H16A	108.9	C32A—C31—H31C	110.9
C15—C16—H16B	108.9	C32A—C31—H31D	110.9
H16A—C16—H16B	107.7	C31—C32—H32A	109.5
C17—C16—C15	113.23 (19)	C31—C32—H32B	109.5
C17—C16—H16A	108.9	C31—C32—H32C	109.5
C17—C16—H16B	108.9	H32A—C32—H32B	109.5
C16—C17—C18	108.57 (18)	H32A—C32—H32C	109.5
C16—C17—C22	111.38 (19)	H32B—C32—H32C	109.5
C16—C17—C28	110.4 (2)	C31—C32A—H32D	109.5
C18—C17—C22	109.36 (18)	C31—C32A—H32E	109.5
C28—C17—C18	109.6 (2)	C31—C32A—H32F	109.5
C28—C17—C22	107.5 (2)	H32D—C32A—H32E	109.5
C13—C18—C17	111.97 (17)	H32D—C32A—H32F	109.5
C13—C18—H18	106.9	H32E—C32A—H32F	109.5

O3—C3—C4—C5	−175.2 (2)	C12—C13—C18—C17	139.8 (2)
O3—C3—C4—C23	67.5 (3)	C12—C13—C18—C19	−93.3 (2)
O3—C3—C4—C24	−50.4 (3)	C13—C14—C15—C16	−37.6 (3)
O11—C11—C12—C13	176.6 (2)	C13—C18—C19—C20	179.58 (18)
C1—C2—C3—O3	−179.1 (2)	C14—C8—C9—C10	165.30 (16)
C1—C2—C3—C4	57.5 (3)	C14—C8—C9—C11	−60.8 (2)
C2—C1—C10—C5	54.0 (2)	C14—C13—C18—C17	−44.3 (3)
C2—C1—C10—C9	167.66 (19)	C14—C13—C18—C19	82.7 (2)
C2—C1—C10—C25	−69.8 (2)	C14—C15—C16—C17	52.9 (3)
C2—C3—C4—C5	−50.5 (3)	C15—C16—C17—C18	−59.7 (3)
C2—C3—C4—C23	−167.9 (2)	C15—C16—C17—C22	179.78 (19)
C2—C3—C4—C24	74.2 (3)	C15—C16—C17—C28	60.4 (3)
C3—C4—C5—C6	179.5 (2)	C16—C17—C18—C13	53.7 (2)
C3—C4—C5—C10	48.8 (3)	C16—C17—C18—C19	−72.4 (2)
C4—C5—C6—C7	161.18 (18)	C16—C17—C22—C21	68.7 (3)
C4—C5—C10—C1	−50.7 (2)	C17—C18—C19—C20	−53.9 (2)
C4—C5—C10—C9	−166.65 (17)	C18—C13—C14—C8	157.40 (17)
C4—C5—C10—C25	69.3 (2)	C18—C13—C14—C15	34.9 (3)
C5—C6—C7—C8	55.6 (3)	C18—C13—C14—C27	−81.3 (2)
C6—C5—C10—C1	177.14 (18)	C18—C17—C22—C21	−51.3 (3)
C6—C5—C10—C9	61.1 (2)	C18—C19—C20—C21	54.6 (3)
C6—C5—C10—C25	−62.9 (2)	C18—C19—C20—C29	173.8 (2)
C6—C7—C8—C9	−44.4 (3)	C18—C19—C20—C30	−67.5 (3)
C6—C7—C8—C14	−163.44 (18)	C19—C20—C21—C22	−54.3 (3)
C6—C7—C8—C26	75.9 (2)	C19—C20—C30—O30	−34.4 (3)
C7—C8—C9—C10	45.5 (2)	C19—C20—C30—O31	147.7 (3)
C7—C8—C9—C11	179.38 (18)	C20—C21—C22—C17	55.4 (3)
C7—C8—C14—C13	176.79 (17)	C21—C20—C30—O30	−156.1 (2)
C7—C8—C14—C15	−59.9 (2)	C21—C20—C30—O31	26.0 (4)
C7—C8—C14—C27	59.1 (2)	C22—C17—C18—C13	175.38 (18)
C8—C9—C10—C1	−168.24 (18)	C22—C17—C18—C19	49.3 (2)
C8—C9—C10—C5	−53.3 (2)	C23—C4—C5—C6	−64.0 (3)
C8—C9—C10—C25	72.0 (2)	C23—C4—C5—C10	165.4 (2)
C8—C9—C11—O11	−146.0 (2)	C24—C4—C5—C6	55.5 (3)
C8—C9—C11—C12	35.9 (3)	C24—C4—C5—C10	−75.1 (2)
C8—C14—C15—C16	−159.76 (19)	C26—C8—C9—C10	−73.8 (2)
C9—C8—C14—C13	56.3 (2)	C26—C8—C9—C11	60.1 (2)
C9—C8—C14—C15	179.69 (17)	C26—C8—C14—C13	−64.1 (2)
C9—C8—C14—C27	−61.3 (2)	C26—C8—C14—C15	59.2 (2)
C9—C11—C12—C13	−5.3 (3)	C26—C8—C14—C27	178.20 (18)
C10—C1—C2—C3	−59.4 (3)	C27—C14—C15—C16	78.1 (2)
C10—C5—C6—C7	−64.8 (2)	C28—C17—C18—C13	−67.0 (2)
C10—C9—C11—O11	−11.3 (3)	C28—C17—C18—C19	166.87 (19)
C10—C9—C11—C12	170.69 (18)	C28—C17—C22—C21	−170.2 (2)
C11—C9—C10—C1	61.1 (2)	C29—C20—C21—C22	−173.5 (2)
C11—C9—C10—C5	176.08 (17)	C29—C20—C30—O30	85.7 (3)
C11—C9—C10—C25	−58.7 (2)	C29—C20—C30—O31	−92.3 (4)
C11—C12—C13—C14	0.5 (3)	C30—O30—C31—C32	−176.2 (5)
C11—C12—C13—C18	176.5 (2)	C30—O30—C31—C32A	−151.2 (7)
C12—C13—C14—C8	−26.7 (3)	C30—C20—C21—C22	69.7 (2)
C12—C13—C14—C15	−149.2 (2)	C31—O30—C30—O31	1.0 (5)
C12—C13—C14—C27	94.7 (2)	C31—O30—C30—C20	−177.0 (2)

(2-morpholinoethyl-GE) top

Crystal data top

C₃₆H₅₇NO₅	D_x = 1.163 Mg m⁻³
M_r = 583.82	Melting point: 478-479 K
Orthorhombic, P2₁2₁2₁	Cu Kα radiation, λ = 1.54178 Å
a = 12.9136 (2) Å	Cell parameters from 20546 reflections
b = 13.7752 (3) Å	θ = 3.9–76.2°
c = 18.7441 (4) Å	µ = 0.60 mm⁻¹
V = 3334.32 (10) Å³	T = 298 K
Z = 4	Plate, colorless
F(000) = 1280	0.4 × 0.15 × 0.05 mm

Data collection top

SuperNova, Dual, Cu at home/near, Atlas diffractometer	6099 independent reflections
Radiation source: micro-focus sealed X-ray tube	5635 reflections with I > 2σ(I)
Detector resolution: 10.3991 pixels mm^-1	R_int = 0.045
ω scans	θ_max = 68.3°, θ_min = 6.4°
Absorption correction: multi-scan CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −15→15
T_min = 0.78, T_max = 1.00	k = −16→16
64824 measured reflections	l = −22→22

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.037	w = 1/[σ²(F_o²) + (0.0586P)² + 0.3153P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.100	(Δ/σ)_max = 0.001
S = 1.04	Δρ_max = 0.10 e Å⁻³
6099 reflections	Δρ_min = −0.16 e Å⁻³
387 parameters	Absolute structure: Flack x determined using 2381 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
0 restraints	Absolute structure parameter: −0.15 (7)

Special details top

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

	x	y	z	U_iso*/U_eq
O1	0.7062 (3)	0.8231 (2)	0.59577 (15)	0.1175 (10)
O3	0.65538 (14)	−0.16260 (16)	0.82993 (12)	0.0767 (6)
H3	0.594289	−0.178572	0.832028	0.115*
O11	0.54649 (12)	0.26207 (13)	0.67561 (11)	0.0661 (5)
O30	0.56759 (12)	0.51704 (12)	0.41328 (11)	0.0620 (4)
O31	0.67744 (17)	0.62505 (13)	0.36652 (11)	0.0734 (5)
N1	0.59458 (18)	0.67050 (17)	0.52685 (12)	0.0643 (5)
C1	0.59157 (15)	0.06282 (16)	0.72346 (12)	0.0478 (5)
H1A	0.533638	0.107420	0.726690	0.057*
H1B	0.589673	0.032984	0.676605	0.057*
C2	0.57905 (17)	−0.01595 (18)	0.78003 (13)	0.0535 (5)
H2A	0.575484	0.014021	0.826799	0.064*
H2B	0.514580	−0.050381	0.771969	0.064*
C3	0.66748 (17)	−0.08698 (17)	0.77847 (13)	0.0516 (5)
H3A	0.667977	−0.117343	0.731191	0.062*
C4	0.77382 (17)	−0.03905 (18)	0.78962 (12)	0.0520 (5)
C5	0.78324 (15)	0.04489 (15)	0.73409 (11)	0.0424 (4)
H5	0.780454	0.012259	0.687676	0.051*
C6	0.88865 (16)	0.09568 (19)	0.73474 (14)	0.0551 (6)
H6A	0.891987	0.140364	0.774672	0.066*
H6B	0.943136	0.047865	0.740603	0.066*
C7	0.90501 (15)	0.15092 (18)	0.66539 (13)	0.0524 (5)
H7A	0.907496	0.104756	0.626354	0.063*
H7B	0.971556	0.183477	0.667396	0.063*
C8	0.82074 (14)	0.22662 (15)	0.64940 (10)	0.0392 (4)
C9	0.71135 (13)	0.18155 (14)	0.66164 (10)	0.0361 (4)
H9	0.703412	0.134508	0.622796	0.043*
C10	0.69357 (14)	0.12058 (15)	0.73126 (10)	0.0401 (4)
C11	0.63064 (15)	0.25939 (15)	0.64578 (12)	0.0445 (5)
C12	0.65543 (15)	0.33144 (16)	0.59114 (12)	0.0466 (5)
H12	0.604905	0.377239	0.580314	0.056*
C13	0.74495 (14)	0.33679 (14)	0.55544 (10)	0.0385 (4)
C14	0.82834 (14)	0.26033 (14)	0.56862 (10)	0.0391 (4)
C15	0.93900 (16)	0.29807 (17)	0.55156 (13)	0.0512 (5)
H15A	0.965704	0.331375	0.593284	0.061*
H15B	0.983591	0.242772	0.542474	0.061*
C16	0.94506 (16)	0.36686 (18)	0.48779 (13)	0.0527 (5)
H16A	0.927957	0.331343	0.444686	0.063*
H16B	1.015505	0.390442	0.483064	0.063*
C17	0.87162 (16)	0.45368 (16)	0.49510 (12)	0.0483 (5)
C18	0.75897 (15)	0.41470 (15)	0.49886 (11)	0.0419 (4)
H18	0.714941	0.469484	0.512734	0.050*
C19	0.71886 (16)	0.37844 (16)	0.42613 (11)	0.0453 (5)
H19A	0.758778	0.322070	0.411781	0.054*
H19B	0.647239	0.358370	0.431200	0.054*
C20	0.72606 (17)	0.45589 (17)	0.36755 (12)	0.0491 (5)
C21	0.83911 (19)	0.4884 (2)	0.36162 (14)	0.0600 (6)
H21A	0.880701	0.434324	0.344933	0.072*
H21B	0.844124	0.539922	0.326524	0.072*
C22	0.88237 (19)	0.52428 (18)	0.43201 (14)	0.0592 (6)
H22A	0.847703	0.584454	0.444333	0.071*
H22B	0.955238	0.538911	0.425505	0.071*
C24	0.7874 (2)	−0.0069 (2)	0.86750 (13)	0.0747 (9)
H24A	0.727201	0.028516	0.882545	0.112*
H24B	0.847372	0.033969	0.871382	0.112*
H24C	0.796125	−0.063002	0.897262	0.112*
C23	0.8562 (2)	−0.1163 (2)	0.7728 (2)	0.0793 (9)
H23A	0.923397	−0.092004	0.785311	0.119*
H23B	0.854562	−0.131166	0.722719	0.119*
H23C	0.841941	−0.174087	0.799689	0.119*
C25	0.6853 (2)	0.18551 (19)	0.79811 (12)	0.0573 (6)
H25A	0.647095	0.243213	0.786617	0.086*
H25B	0.753471	0.202965	0.813986	0.086*
H25C	0.650153	0.150732	0.835312	0.086*
C26	0.83772 (19)	0.31309 (18)	0.70015 (12)	0.0529 (5)
H26A	0.845566	0.289683	0.748089	0.079*
H26B	0.779116	0.355851	0.697745	0.079*
H26C	0.899045	0.347646	0.686259	0.079*
C27	0.8064 (2)	0.17643 (16)	0.51518 (11)	0.0521 (5)
H27A	0.733685	0.161792	0.515267	0.078*
H27B	0.844712	0.119837	0.529173	0.078*
H27C	0.827144	0.195867	0.468128	0.078*
C28	0.8962 (2)	0.51063 (19)	0.56308 (15)	0.0654 (7)
H28A	0.881997	0.470873	0.603991	0.098*
H28B	0.854010	0.567968	0.564857	0.098*
H28C	0.967955	0.528786	0.563045	0.098*
C29	0.6914 (2)	0.4131 (2)	0.29565 (13)	0.0634 (6)
H29A	0.621299	0.390575	0.299437	0.095*
H29B	0.735756	0.359756	0.283192	0.095*
H29C	0.695652	0.462185	0.259421	0.095*
C30	0.65707 (18)	0.54289 (18)	0.38234 (12)	0.0519 (5)
C31	0.4942 (2)	0.5932 (2)	0.4296 (2)	0.0784 (9)
H31A	0.424716	0.571298	0.418487	0.094*
H31B	0.508991	0.649759	0.400514	0.094*
C32	0.5003 (2)	0.6204 (2)	0.5070 (2)	0.0842 (9)
H32A	0.441635	0.661488	0.518575	0.101*
H32B	0.494448	0.561802	0.535496	0.101*
C33	0.6052 (4)	0.6770 (3)	0.60412 (18)	0.1010 (13)
H33A	0.606160	0.612222	0.624346	0.121*
H33B	0.546068	0.711282	0.623743	0.121*
C34	0.7019 (5)	0.7288 (3)	0.6241 (2)	0.1235 (18)
H34A	0.706528	0.732339	0.675636	0.148*
H34B	0.760924	0.692014	0.606974	0.148*
C35	0.6959 (4)	0.8180 (3)	0.5211 (2)	0.1120 (14)
H35A	0.754869	0.783387	0.501587	0.134*
H35B	0.696711	0.883257	0.501709	0.134*
C36	0.5989 (3)	0.7684 (2)	0.49816 (18)	0.0813 (9)
H36A	0.539449	0.805062	0.514704	0.098*
H36B	0.596289	0.765834	0.446476	0.098*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.167 (3)	0.0917 (18)	0.0939 (17)	0.0009 (19)	−0.0273 (18)	−0.0231 (15)
O3	0.0559 (10)	0.0777 (12)	0.0966 (14)	−0.0231 (9)	−0.0196 (10)	0.0438 (11)
O11	0.0406 (8)	0.0677 (11)	0.0898 (13)	0.0168 (8)	0.0247 (8)	0.0184 (10)
O30	0.0442 (8)	0.0518 (9)	0.0901 (12)	0.0005 (7)	0.0001 (8)	0.0005 (9)
O31	0.0911 (13)	0.0538 (10)	0.0753 (12)	0.0014 (10)	0.0137 (10)	0.0215 (9)
N1	0.0676 (13)	0.0618 (12)	0.0635 (12)	0.0083 (11)	0.0107 (10)	0.0028 (10)
C1	0.0307 (9)	0.0537 (12)	0.0590 (12)	−0.0053 (8)	−0.0038 (8)	0.0058 (10)
C2	0.0380 (10)	0.0619 (14)	0.0606 (13)	−0.0125 (10)	−0.0019 (9)	0.0068 (11)
C3	0.0466 (12)	0.0509 (12)	0.0573 (12)	−0.0129 (10)	−0.0107 (9)	0.0122 (10)
C4	0.0398 (10)	0.0605 (13)	0.0557 (12)	−0.0098 (10)	−0.0100 (9)	0.0163 (10)
C5	0.0337 (9)	0.0498 (11)	0.0438 (10)	−0.0036 (8)	−0.0048 (8)	0.0047 (9)
C6	0.0331 (10)	0.0676 (14)	0.0648 (14)	−0.0057 (10)	−0.0085 (9)	0.0210 (12)
C7	0.0287 (9)	0.0633 (14)	0.0652 (13)	0.0017 (9)	0.0005 (9)	0.0192 (11)
C8	0.0296 (9)	0.0453 (10)	0.0426 (9)	−0.0002 (8)	−0.0005 (7)	0.0008 (8)
C9	0.0287 (8)	0.0403 (10)	0.0392 (9)	0.0012 (7)	−0.0003 (7)	−0.0043 (7)
C10	0.0334 (9)	0.0458 (10)	0.0411 (9)	−0.0051 (8)	0.0005 (7)	−0.0017 (8)
C11	0.0328 (9)	0.0468 (11)	0.0540 (11)	0.0037 (8)	0.0053 (8)	−0.0021 (9)
C12	0.0344 (9)	0.0450 (11)	0.0602 (12)	0.0098 (8)	0.0040 (9)	0.0051 (9)
C13	0.0350 (9)	0.0369 (9)	0.0437 (10)	0.0007 (8)	−0.0007 (8)	−0.0035 (8)
C14	0.0319 (9)	0.0421 (10)	0.0435 (9)	0.0033 (8)	0.0040 (7)	−0.0005 (8)
C15	0.0329 (10)	0.0583 (13)	0.0623 (13)	0.0061 (9)	0.0076 (9)	0.0111 (11)
C16	0.0338 (10)	0.0616 (13)	0.0628 (13)	−0.0003 (9)	0.0083 (9)	0.0113 (11)
C17	0.0388 (10)	0.0474 (11)	0.0586 (12)	−0.0051 (9)	−0.0010 (9)	0.0034 (10)
C18	0.0357 (10)	0.0398 (9)	0.0503 (11)	0.0018 (8)	0.0003 (8)	0.0012 (9)
C19	0.0388 (10)	0.0466 (11)	0.0506 (11)	−0.0030 (9)	−0.0005 (8)	0.0046 (9)
C20	0.0461 (11)	0.0532 (12)	0.0478 (11)	−0.0045 (10)	0.0023 (9)	0.0078 (9)
C21	0.0495 (13)	0.0697 (15)	0.0609 (13)	−0.0069 (11)	0.0086 (11)	0.0169 (12)
C22	0.0465 (12)	0.0580 (14)	0.0730 (15)	−0.0114 (11)	−0.0030 (11)	0.0140 (12)
C24	0.0685 (16)	0.099 (2)	0.0568 (14)	−0.0355 (16)	−0.0232 (12)	0.0258 (14)
C23	0.0505 (14)	0.0716 (17)	0.116 (2)	0.0069 (13)	−0.0020 (14)	0.0403 (18)
C25	0.0659 (14)	0.0602 (14)	0.0459 (11)	−0.0112 (12)	0.0104 (10)	−0.0082 (10)
C26	0.0547 (13)	0.0567 (13)	0.0473 (11)	−0.0160 (10)	−0.0053 (9)	−0.0027 (10)
C27	0.0648 (14)	0.0458 (11)	0.0457 (11)	0.0090 (11)	0.0087 (10)	−0.0039 (9)
C28	0.0654 (15)	0.0565 (14)	0.0743 (16)	−0.0099 (12)	−0.0124 (13)	−0.0027 (12)
C29	0.0679 (15)	0.0712 (16)	0.0511 (13)	−0.0057 (14)	0.0016 (11)	0.0032 (11)
C30	0.0551 (13)	0.0530 (13)	0.0475 (11)	−0.0016 (10)	−0.0050 (10)	0.0117 (10)
C31	0.0465 (13)	0.0687 (17)	0.120 (3)	0.0079 (12)	−0.0085 (15)	−0.0089 (17)
C32	0.0622 (16)	0.0739 (18)	0.116 (3)	0.0039 (14)	0.0289 (17)	−0.0073 (18)
C33	0.164 (4)	0.075 (2)	0.0640 (18)	0.018 (2)	0.021 (2)	0.0049 (16)
C34	0.189 (5)	0.091 (3)	0.090 (3)	0.035 (3)	−0.049 (3)	−0.025 (2)
C35	0.148 (4)	0.099 (3)	0.089 (2)	−0.047 (3)	0.003 (2)	−0.009 (2)
C36	0.103 (2)	0.0662 (17)	0.0749 (18)	−0.0001 (17)	−0.0036 (17)	0.0050 (15)

Geometric parameters (Å, º) top

O1—C34	1.404 (5)	C17—C18	1.552 (3)
O1—C35	1.407 (5)	C17—C22	1.537 (3)
O3—H3	0.8200	C17—C28	1.530 (3)
O3—C3	1.428 (3)	C18—H18	0.9800
O11—C11	1.223 (3)	C18—C19	1.541 (3)
O30—C30	1.341 (3)	C19—H19A	0.9700
O30—C31	1.447 (3)	C19—H19B	0.9700
O31—C30	1.199 (3)	C19—C20	1.534 (3)
N1—C32	1.449 (4)	C20—C21	1.531 (3)
N1—C33	1.458 (4)	C20—C29	1.538 (3)
N1—C36	1.453 (4)	C20—C30	1.519 (3)
C1—H1A	0.9700	C21—H21A	0.9700
C1—H1B	0.9700	C21—H21B	0.9700
C1—C2	1.526 (3)	C21—C22	1.516 (4)
C1—C10	1.546 (3)	C22—H22A	0.9700
C2—H2A	0.9700	C22—H22B	0.9700
C2—H2B	0.9700	C24—H24A	0.9600
C2—C3	1.504 (3)	C24—H24B	0.9600
C3—H3A	0.9800	C24—H24C	0.9600
C3—C4	1.538 (3)	C23—H23A	0.9600
C4—C5	1.560 (3)	C23—H23B	0.9600
C4—C24	1.536 (4)	C23—H23C	0.9600
C4—C23	1.537 (4)	C25—H25A	0.9600
C5—H5	0.9800	C25—H25B	0.9600
C5—C6	1.531 (3)	C25—H25C	0.9600
C5—C10	1.559 (3)	C26—H26A	0.9600
C6—H6A	0.9700	C26—H26B	0.9600
C6—H6B	0.9700	C26—H26C	0.9600
C6—C7	1.521 (3)	C27—H27A	0.9600
C7—H7A	0.9700	C27—H27B	0.9600
C7—H7B	0.9700	C27—H27C	0.9600
C7—C8	1.537 (3)	C28—H28A	0.9600
C8—C9	1.560 (2)	C28—H28B	0.9600
C8—C14	1.587 (3)	C28—H28C	0.9600
C8—C26	1.540 (3)	C29—H29A	0.9600
C9—H9	0.9800	C29—H29B	0.9600
C9—C10	1.569 (3)	C29—H29C	0.9600
C9—C11	1.525 (3)	C31—H31A	0.9700
C10—C25	1.543 (3)	C31—H31B	0.9700
C11—C12	1.462 (3)	C31—C32	1.500 (5)
C12—H12	0.9300	C32—H32A	0.9700
C12—C13	1.338 (3)	C32—H32B	0.9700
C13—C14	1.527 (3)	C33—H33A	0.9700
C13—C18	1.520 (3)	C33—H33B	0.9700
C14—C15	1.554 (3)	C33—C34	1.485 (7)
C14—C27	1.556 (3)	C34—H34A	0.9700
C15—H15A	0.9700	C34—H34B	0.9700
C15—H15B	0.9700	C35—H35A	0.9700
C15—C16	1.527 (3)	C35—H35B	0.9700
C16—H16A	0.9700	C35—C36	1.490 (5)
C16—H16B	0.9700	C36—H36A	0.9700
C16—C17	1.532 (3)	C36—H36B	0.9700

C34—O1—C35	109.0 (3)	C18—C19—H19A	109.0
C3—O3—H3	109.5	C18—C19—H19B	109.0
C30—O30—C31	117.6 (2)	H19A—C19—H19B	107.8
C32—N1—C33	111.3 (3)	C20—C19—C18	112.78 (17)
C32—N1—C36	112.3 (3)	C20—C19—H19A	109.0
C36—N1—C33	107.9 (3)	C20—C19—H19B	109.0
H1A—C1—H1B	107.8	C19—C20—C29	110.07 (19)
C2—C1—H1A	109.0	C21—C20—C19	108.25 (18)
C2—C1—H1B	109.0	C21—C20—C29	109.0 (2)
C2—C1—C10	113.00 (17)	C30—C20—C19	112.50 (18)
C10—C1—H1A	109.0	C30—C20—C21	110.0 (2)
C10—C1—H1B	109.0	C30—C20—C29	107.0 (2)
C1—C2—H2A	109.3	C20—C21—H21A	109.1
C1—C2—H2B	109.3	C20—C21—H21B	109.1
H2A—C2—H2B	108.0	H21A—C21—H21B	107.8
C3—C2—C1	111.63 (19)	C22—C21—C20	112.6 (2)
C3—C2—H2A	109.3	C22—C21—H21A	109.1
C3—C2—H2B	109.3	C22—C21—H21B	109.1
O3—C3—C2	112.2 (2)	C17—C22—H22A	108.4
O3—C3—H3A	107.5	C17—C22—H22B	108.4
O3—C3—C4	108.61 (17)	C21—C22—C17	115.5 (2)
C2—C3—H3A	107.5	C21—C22—H22A	108.4
C2—C3—C4	113.33 (19)	C21—C22—H22B	108.4
C4—C3—H3A	107.5	H22A—C22—H22B	107.5
C3—C4—C5	107.28 (16)	C4—C24—H24A	109.5
C24—C4—C3	110.8 (2)	C4—C24—H24B	109.5
C24—C4—C5	114.3 (2)	C4—C24—H24C	109.5
C24—C4—C23	108.4 (2)	H24A—C24—H24B	109.5
C23—C4—C3	107.0 (2)	H24A—C24—H24C	109.5
C23—C4—C5	108.8 (2)	H24B—C24—H24C	109.5
C4—C5—H5	104.4	C4—C23—H23A	109.5
C6—C5—C4	113.75 (17)	C4—C23—H23B	109.5
C6—C5—H5	104.4	C4—C23—H23C	109.5
C6—C5—C10	110.80 (17)	H23A—C23—H23B	109.5
C10—C5—C4	117.41 (17)	H23A—C23—H23C	109.5
C10—C5—H5	104.4	H23B—C23—H23C	109.5
C5—C6—H6A	109.6	C10—C25—H25A	109.5
C5—C6—H6B	109.6	C10—C25—H25B	109.5
H6A—C6—H6B	108.1	C10—C25—H25C	109.5
C7—C6—C5	110.21 (17)	H25A—C25—H25B	109.5
C7—C6—H6A	109.6	H25A—C25—H25C	109.5
C7—C6—H6B	109.6	H25B—C25—H25C	109.5
C6—C7—H7A	108.7	C8—C26—H26A	109.5
C6—C7—H7B	108.7	C8—C26—H26B	109.5
C6—C7—C8	114.07 (18)	C8—C26—H26C	109.5
H7A—C7—H7B	107.6	H26A—C26—H26B	109.5
C8—C7—H7A	108.7	H26A—C26—H26C	109.5
C8—C7—H7B	108.7	H26B—C26—H26C	109.5
C7—C8—C9	110.03 (16)	C14—C27—H27A	109.5
C7—C8—C14	109.93 (16)	C14—C27—H27B	109.5
C7—C8—C26	107.67 (17)	C14—C27—H27C	109.5
C9—C8—C14	108.22 (14)	H27A—C27—H27B	109.5
C26—C8—C9	110.24 (16)	H27A—C27—H27C	109.5
C26—C8—C14	110.75 (17)	H27B—C27—H27C	109.5
C8—C9—H9	104.4	C17—C28—H28A	109.5
C8—C9—C10	117.89 (15)	C17—C28—H28B	109.5
C10—C9—H9	104.4	C17—C28—H28C	109.5
C11—C9—C8	108.09 (15)	H28A—C28—H28B	109.5
C11—C9—H9	104.4	H28A—C28—H28C	109.5
C11—C9—C10	116.02 (15)	H28B—C28—H28C	109.5
C1—C10—C5	106.97 (16)	C20—C29—H29A	109.5
C1—C10—C9	108.76 (15)	C20—C29—H29B	109.5
C5—C10—C9	106.12 (15)	C20—C29—H29C	109.5
C25—C10—C1	108.43 (17)	H29A—C29—H29B	109.5
C25—C10—C5	114.29 (18)	H29A—C29—H29C	109.5
C25—C10—C9	112.04 (16)	H29B—C29—H29C	109.5
O11—C11—C9	122.66 (19)	O30—C30—C20	112.01 (19)
O11—C11—C12	119.65 (19)	O31—C30—O30	123.1 (2)
C12—C11—C9	117.68 (16)	O31—C30—C20	124.8 (2)
C11—C12—H12	117.4	O30—C31—H31A	109.5
C13—C12—C11	125.25 (18)	O30—C31—H31B	109.5
C13—C12—H12	117.4	O30—C31—C32	110.6 (3)
C12—C13—C14	119.39 (18)	H31A—C31—H31B	108.1
C12—C13—C18	119.40 (18)	C32—C31—H31A	109.5
C18—C13—C14	121.07 (16)	C32—C31—H31B	109.5
C13—C14—C8	108.22 (15)	N1—C32—C31	114.2 (2)
C13—C14—C15	112.62 (16)	N1—C32—H32A	108.7
C13—C14—C27	106.25 (16)	N1—C32—H32B	108.7
C15—C14—C8	110.56 (15)	C31—C32—H32A	108.7
C15—C14—C27	106.49 (17)	C31—C32—H32B	108.7
C27—C14—C8	112.69 (16)	H32A—C32—H32B	107.6
C14—C15—H15A	108.6	N1—C33—H33A	109.4
C14—C15—H15B	108.6	N1—C33—H33B	109.4
H15A—C15—H15B	107.6	N1—C33—C34	111.0 (3)
C16—C15—C14	114.57 (17)	H33A—C33—H33B	108.0
C16—C15—H15A	108.6	C34—C33—H33A	109.4
C16—C15—H15B	108.6	C34—C33—H33B	109.4
C15—C16—H16A	109.1	O1—C34—C33	112.5 (4)
C15—C16—H16B	109.1	O1—C34—H34A	109.1
C15—C16—C17	112.48 (18)	O1—C34—H34B	109.1
H16A—C16—H16B	107.8	C33—C34—H34A	109.1
C17—C16—H16A	109.1	C33—C34—H34B	109.1
C17—C16—H16B	109.1	H34A—C34—H34B	107.8
C16—C17—C18	108.31 (17)	O1—C35—H35A	109.0
C16—C17—C22	111.65 (19)	O1—C35—H35B	109.0
C22—C17—C18	109.78 (17)	O1—C35—C36	112.9 (3)
C28—C17—C16	110.3 (2)	H35A—C35—H35B	107.8
C28—C17—C18	109.51 (19)	C36—C35—H35A	109.0
C28—C17—C22	107.31 (19)	C36—C35—H35B	109.0
C13—C18—C17	112.80 (16)	N1—C36—C35	110.5 (3)
C13—C18—H18	106.8	N1—C36—H36A	109.5
C13—C18—C19	110.38 (16)	N1—C36—H36B	109.5
C17—C18—H18	106.8	C35—C36—H36A	109.5
C19—C18—C17	112.76 (17)	C35—C36—H36B	109.5
C19—C18—H18	106.8	H36A—C36—H36B	108.1

O1—C35—C36—N1	−58.2 (5)	C13—C14—C15—C16	−36.1 (3)
O3—C3—C4—C5	−178.4 (2)	C13—C18—C19—C20	177.17 (16)
O3—C3—C4—C24	−53.1 (3)	C14—C8—C9—C10	165.62 (15)
O3—C3—C4—C23	64.9 (3)	C14—C8—C9—C11	−60.35 (19)
O11—C11—C12—C13	179.2 (2)	C14—C13—C18—C17	−38.8 (2)
O30—C31—C32—N1	69.8 (3)	C14—C13—C18—C19	88.3 (2)
N1—C33—C34—O1	58.4 (5)	C14—C15—C16—C17	54.7 (3)
C1—C2—C3—O3	−178.46 (19)	C15—C16—C17—C18	−61.5 (2)
C1—C2—C3—C4	58.1 (2)	C15—C16—C17—C22	177.49 (19)
C2—C1—C10—C5	52.6 (2)	C15—C16—C17—C28	58.3 (3)
C2—C1—C10—C9	166.84 (18)	C16—C17—C18—C13	52.2 (2)
C2—C1—C10—C25	−71.1 (2)	C16—C17—C18—C19	−73.7 (2)
C2—C3—C4—C5	−53.0 (3)	C16—C17—C22—C21	71.7 (3)
C2—C3—C4—C24	72.4 (3)	C17—C18—C19—C20	−55.7 (2)
C2—C3—C4—C23	−169.6 (2)	C18—C13—C14—C8	152.04 (17)
C3—C4—C5—C6	−175.9 (2)	C18—C13—C14—C15	29.5 (3)
C3—C4—C5—C10	52.4 (3)	C18—C13—C14—C27	−86.7 (2)
C4—C5—C6—C7	161.1 (2)	C18—C17—C22—C21	−48.4 (3)
C4—C5—C10—C1	−52.3 (2)	C18—C19—C20—C21	57.4 (2)
C4—C5—C10—C9	−168.29 (16)	C18—C19—C20—C29	176.42 (19)
C4—C5—C10—C25	67.7 (2)	C18—C19—C20—C30	−64.4 (2)
C5—C6—C7—C8	57.4 (3)	C19—C20—C21—C22	−55.7 (3)
C6—C5—C10—C1	174.67 (17)	C19—C20—C30—O30	−36.3 (3)
C6—C5—C10—C9	58.7 (2)	C19—C20—C30—O31	145.9 (2)
C6—C5—C10—C25	−65.3 (2)	C20—C21—C22—C17	53.8 (3)
C6—C7—C8—C9	−46.5 (3)	C21—C20—C30—O30	−157.1 (2)
C6—C7—C8—C14	−165.62 (19)	C21—C20—C30—O31	25.2 (3)
C6—C7—C8—C26	73.6 (2)	C22—C17—C18—C13	174.32 (18)
C7—C8—C9—C10	45.5 (2)	C22—C17—C18—C19	48.4 (2)
C7—C8—C9—C11	179.52 (17)	C24—C4—C5—C6	60.8 (3)
C7—C8—C14—C13	−178.86 (16)	C24—C4—C5—C10	−70.9 (3)
C7—C8—C14—C15	−55.1 (2)	C23—C4—C5—C6	−60.5 (3)
C7—C8—C14—C27	64.0 (2)	C23—C4—C5—C10	167.8 (2)
C8—C9—C10—C1	−166.04 (16)	C26—C8—C9—C10	−73.1 (2)
C8—C9—C10—C5	−51.3 (2)	C26—C8—C9—C11	60.9 (2)
C8—C9—C10—C25	74.1 (2)	C26—C8—C14—C13	−60.0 (2)
C8—C9—C11—O11	−149.9 (2)	C26—C8—C14—C15	63.8 (2)
C8—C9—C11—C12	31.8 (2)	C26—C8—C14—C27	−177.19 (17)
C8—C14—C15—C16	−157.29 (19)	C27—C14—C15—C16	80.0 (2)
C9—C8—C14—C13	60.9 (2)	C28—C17—C18—C13	−68.1 (2)
C9—C8—C14—C15	−175.29 (16)	C28—C17—C18—C19	166.00 (19)
C9—C8—C14—C27	−56.2 (2)	C28—C17—C22—C21	−167.3 (2)
C9—C11—C12—C13	−2.5 (3)	C29—C20—C21—C22	−175.4 (2)
C10—C1—C2—C3	−57.9 (2)	C29—C20—C30—O30	84.6 (2)
C10—C5—C6—C7	−64.1 (2)	C29—C20—C30—O31	−93.1 (3)
C10—C9—C11—O11	−14.9 (3)	C30—O30—C31—C32	−100.0 (3)
C10—C9—C11—C12	166.76 (18)	C30—C20—C21—C22	67.6 (3)
C11—C9—C10—C1	63.5 (2)	C31—O30—C30—O31	−1.7 (4)
C11—C9—C10—C5	178.25 (16)	C31—O30—C30—C20	−179.4 (2)
C11—C9—C10—C25	−56.4 (2)	C32—N1—C33—C34	−179.8 (3)
C11—C12—C13—C14	3.0 (3)	C32—N1—C36—C35	178.7 (3)
C11—C12—C13—C18	178.79 (19)	C33—N1—C32—C31	−168.4 (3)
C12—C13—C14—C8	−32.2 (2)	C33—N1—C36—C35	55.7 (4)
C12—C13—C14—C15	−154.7 (2)	C34—O1—C35—C36	56.9 (6)
C12—C13—C14—C27	89.0 (2)	C35—O1—C34—C33	−56.8 (5)
C12—C13—C18—C17	145.4 (2)	C36—N1—C32—C31	70.6 (3)
C12—C13—C18—C19	−87.4 (2)	C36—N1—C33—C34	−56.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O11ⁱ	0.82	2.00	2.808 (2)	169

Symmetry code: (i) −x+1, y−1/2, −z+3/2.

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