Crystal structure and Hirshfeld surface analysis of the methanol solvate of sclareol, a labdane-type diterpenoid

Bibi, M.; Choudhary, M.I.; Yousuf, S.

doi:10.1107/S2056989020001474

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ISSN: 2056-9890

Volume 76| Part 3| March 2020| Pages 294-297

https://doi.org/10.1107/S2056989020001474

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Crystal structure and Hirshfeld surface analysis of the methanol solvate of sclareol, a labdane-type diterpenoid

Memoona Bibi,^a M. Iqbal Choudhary ^a and Sammer Yousuf ^a ^*

^aH. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi-75270, Pakistan
^*Correspondence e-mail: dr.sammer.yousuf@gmail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 15 January 2020; accepted 3 February 2020; online 6 February 2020)

The title compound, C₂₀H₃₆O₂·CH₃OH [systematic name: (3S)-4-[(S)-3-hydroxy-3-methylpent-4-en-1-yl]-3,4a,8,8-tetramethyldecahydronaphthalen-3-ol methanol monosolvate], is a methanol solvate of sclareol, a diterpene oil isolated from the medicinally important medicinal herb Salvia sclarea, commonly known as clary sage. It crystallizes in space group P1 (No. 1) with Z′ = 2. The sclareol molecule comprises two trans-fused cyclohexane rings, each having an equatorially oriented hydroxyl group, and a 3-methylpent-1-en-3-ol side chain. In the crystal, O_s—H⋯O_s, O_s—H⋯O_m, O_m—H⋯O_s and O_m—H⋯O_m (s = sclareol, m = methanol) hydrogen bonds connect neighboring molecules into infinite [010] chains. The title compound exhibits weak anti-leishmanial activity (IC₅₀ = 66.4 ± 1.0 µM ml⁻¹) against standard miltefosine (IC₅₀ = 25.8 ± 0.2 µM ml⁻¹).

Keywords: labdane diterpene; Salvia sclarea L; clary sage; solvate; Hirshfeld surface analysis; leishmaniasis; crystal structure.

CCDC reference: 1981522

1. Chemical context

Sclareol, a labdane diterpene, is an important component of Salvia sclarea L., commonly known as clary sage, a medicinal herb mostly found in Mediterranean countries and southern Europe (Kouzi & McChesney, 1990 ; Acimovic et al., 2018 ). Sclareol is also reported from Cleome spinose B, Cistus creticus C, and Nicotiana glutinosa S (Caniard et al., 2012 ). Labdanes show various biological and pharmacological activities (Singh et al., 1999 ), including antifungal, antibacterial, growth-regulating activity, and cytostatic and cytotoxic effects against HL60 human leukemic cell lines (Kouzi et al., 1993 ; Dimas et al., 2001 ). Sclareol is also used commercially as a fixative in perfumery and as a flavouring agent in the tobacco industry (Kouzi & McChesney, 1990).

The presence of solvent molecules of crystallization (Aitipamula et al., 2012 ) can significantly influence the geometry of the respective pharmaceutical molecule (Chen et al., 2017 ). The crystal structure of sclareol (orthorhombic, space group P2₁2₁2₁) has been described (Nagashima et al., 1997 ). We now describe the crystal structure of the methanol solvate of sclareol (1), which results in a change of space group to triclinic P1. Leishmaniasis is a major infectious disease caused by various species of the genus Leishmania. Currently there is no effective drug or vaccine against leishmanicidal disease commercially available (Tavares et al., 2018 ). In the current study, the anti-leishmanial activity of 1 was also investigated.

2. Structural commentary

The asymmetric unit (and unit cell) of 1 consists of two independent sclareol molecules and two methanol solvent molecules (Fig. 1). The sclareol skeleton comprises two trans-fused cyclohexane rings, A (C1–C5/C10) and B (C5–C10), which exist in chair conformations, having puckering parameters Q = 0.556 (3) Å, θ = 3.4 (3)°, φ = 26 (4)°, and Q = 0.589 (3) Å, θ = 7.1 (3)°, φ = 347 (2)°, respectively. Ring A bears an axially oriented methyl group at C10 while ring B has an equatorially oriented hydroxyl group and 3-methylpent-1-en-3-ol side chain attached at C8 and C9, respectively. The C11—C9—C8—C17 and C11′—C9′—C8′—C17′ torsion angles of 58.7 (3) and 57.4 (3)°, respectively, indicate that the methyl group and the 3-methylpent-1-en-3-ol side chain are anti to each other in both molecules. The configurations of the stereogenic centres are as follows: C5 S, C8 R, C9 R, C10 S and C13 R; C5′ S, C8′ R, C9′ R, C10′ S and C13′ R.

Figure 1
The molecular structure of 1 with displacement ellipsoids drawn at the 30% probability level.

3. Supramolecular features and Hirshfeld surface analysis

The insertion of the methanol solvent into the crystal alters the previously reported orthorhombic P2₁2₁2₁ crystal symmetry of sclareol (Nagashima et al., 1997) to triclinic P1. The O—H⋯O hydrogen-bonding interactions (Table 1) including O1—H1⋯O2′, O2—H2⋯O1′ and O1′—H1′⋯O1 with H⋯A distances of 1.97 (4), 1.96 (5) and 1.87 (5) Å, respectively, generate R₂²(10) ring motifs (Fig. 2). The O3 methanol solvent molecule links to a sclareol host via an O—H⋯O hydrogen bond and the O3′ methanol molecule links to the O3 methanol molecule (Fig. 3). Taken together, the hydrogen bonds generate infinite [010] chains in the crystal.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2′	0.87 (4)	1.97 (4)	2.816 (2)	163 (4)
O2—H2⋯O1′	0.81 (5)	1.96 (5)	2.762 (2)	167 (4)
O3—H3⋯O2	0.88 (4)	1.89 (5)	2.744 (3)	164 (4)
O1′—H1′⋯O1	0.88 (5)	1.87 (5)	2.744 (2)	170 (4)
O2′—H2′⋯O3′ⁱ	0.76 (5)	2.08 (5)	2.833 (3)	169 (5)
O3′—H3′⋯O3	0.90 (5)	1.89 (5)	2.753 (3)	160 (4)
Symmetry code: (i) x, y+1, z.

Figure 2
Fragment of 1 showing O—H⋯O hydrogen bonds.

Figure 3
Packing diagram of 1 showing the formation of a [010] chain of molecules linked by O—H⋯O hydrogen bonds (dotted lines).

The Hirshfeld surface (Spackman & Jayatilaka, 2009 ; Capozzi et al., 2019 ) mapped over d_norm for 1 is shown in Fig. 4; red spots indicate the areas of the molecular surfaces where strong interactions occur. The two-dimensional fingerprint plots (Fig. 5) indicate a dominant contribution from H⋯H contacts (89.7%) to the Hirshfeld surface; distinct spikes denote the O⋯H/H⋯O interactions (10.7%) while C⋯H/H⋯C contacts contribute a negligible percentage (1.5%) towards the total generated Hirshfeld surface. Views of the Hirshfeld surface mapped over shape-index and curvature are shown in the supporting information.

Figure 4
Hirshfeld surface mapped over d_norm of 1 with neighboring molecules linked via O—H⋯O hydrogen bonds (dashed lines).

Figure 5
Two-dimensional Hirshfeld fingerprint plots for 1.

4. In vitro anti-leishmanial activity

An in vitro anti-leishmanial assay of compound 1 was evaluated against L. major promastigoates. The title compound has a relatively weak anti-leishmanial activity [(IC₅₀ = 66.4 ± 1.0 µM ml⁻¹) against the standard miltefosine drug (IC₅₀ = 25.8 ± 0.2 µM ml⁻¹); however, no activity was observed against tested standard pentamidine (IC₅₀ = 9.24 ± 0.005 µM ml⁻¹) and amphotericin B (IC₅₀ = 0.42 ± 0.005 µM ml⁻¹).

5. Database survey

A search of the Cambridge Structural Database (CSD version 5.40, update of November 2018; Groom et al., 2016 ) gave five hits for similar diterpenoids having two trans-fused cyclohexane rings along with an equatorially oriented 3-methylpent-1-en-3-ol side chain, viz. refcodes JOBLUH (Aranda et al., 1991 ), RULHAH (Nagashima et al., 1997), KADLIK (Rodríguez et al., 1989 ), MIFWED (Kooijman et al., 2002 ) and MIDNIZ (Häfner et al., 2018 ). RULHAH {systematic name: (3S)-4-(S)-3-hydroxy-3-methylpent-4-en-1-yl)-3,4a,8,8-tetramethyldecahydronaphthalen-3-ol} is the unsolvated crystal structure of sclareol. The other four compounds belong to the same class of diterpene with different substituents.

6. Crystallization

Purified sclareol was taken from the molecular bank facility of the Dr Panjwani Center for Molecular Medicine and Drug Research, ICCBS, University of Karachi, Pakistan. The procedure for isolation and purification has already been described (Shawl et al., 1999 ). Crystallization was carried out in a 1:1 solvent mixture of acetonitrile and methanol. Colourless blocks of 1 were obtained by slow evaporation at 277 K after two weeks

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. All the C-bound H atoms were located with idealized geometry and refined with C—H = 0.95–1.00 Å, having U_iso(H) = 1.5U_eq(CH₃) and 1.2U_eq (CH₂, CH). The O-bound H atoms were found in difference-Fourier maps and their positions freely refined with U_iso(H) = 1.2U_eq(O).

Table 2
Experimental details

Crystal data
Chemical formula	C₂₀H₃₆O₂·CH₄O
M_r	340.53
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	6.1728 (3), 12.3721 (6), 13.6788 (7)
α, β, γ (°)	84.302 (2), 80.846 (2), 80.909 (2)
V (Å³)	1015.45 (9)
Z	2
Radiation type	Cu Kα
μ (mm⁻¹)	0.56
Crystal size (mm)	0.38 × 0.23 × 0.13

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	28545, 7074, 7020
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.110, 1.01
No. of reflections	7074
No. of parameters	464
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.21
Absolute structure parameter	0.16 (18)
Computer programs: APEX2 and SAINT (Bruker, 2012 ), SHELXT2014/5 (Sheldrick, 2015a ) and SHELXL2016/6 (Sheldrick, 2015b ).

Supporting information

CCDC reference: 1981522

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989020001474/hb7890sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989020001474/hb7890Isup2.hkl

Hirshfeld curvature and shape index. DOI: https://doi.org/10.1107/S2056989020001474/hb7890sup3.docx

Supporting information file. DOI: https://doi.org/10.1107/S2056989020001474/hb7890Isup4.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2015); software used to prepare material for publication: SHELXTL (Sheldrick, 2015b).

(3S)-4-[(S)-3-Hydroxy-3-methylpent-4-en-1-yl]-3,4a,8,8-tetramethyldecahydronaphthalen-3-ol methanol monosolvate top

Crystal data top

C₂₀H₃₆O₂·CH₄O	Z = 2
M_r = 340.53	F(000) = 378
Triclinic, P1	D_x = 1.110 Mg m⁻³
a = 6.1728 (3) Å	Cu Kα radiation, λ = 1.54178 Å
b = 12.3721 (6) Å	Cell parameters from 9050 reflections
c = 13.6788 (7) Å	θ = 7.8–68.3°
α = 84.302 (2)°	µ = 0.56 mm⁻¹
β = 80.846 (2)°	T = 100 K
γ = 80.909 (2)°	Block, colourless
V = 1015.45 (9) Å³	0.38 × 0.23 × 0.13 mm

Data collection top

Bruker APEXII CCD diffractometer	R_int = 0.028
φ and ω scans	θ_max = 68.2°, θ_min = 5.1°
28545 measured reflections	h = −7→7
7074 independent reflections	k = −14→14
7020 reflections with I > 2σ(I)	l = −16→16

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.110	w = 1/[σ²(F_o²) + (0.081P)² + 0.2189P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.002
7074 reflections	Δρ_max = 0.50 e Å⁻³
464 parameters	Δρ_min = −0.21 e Å⁻³
3 restraints

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
O1	0.4784 (3)	0.64520 (15)	0.53573 (12)	0.0254 (4)
O2	0.5887 (3)	0.29578 (14)	0.62956 (12)	0.0168 (3)
O3	0.5603 (4)	0.08465 (17)	0.59341 (16)	0.0356 (5)
C1	0.3517 (4)	0.6326 (2)	0.89758 (17)	0.0193 (5)
H1A	0.318778	0.556226	0.910076	0.023*
H1B	0.514599	0.629395	0.881628	0.023*
C2	0.2703 (4)	0.6926 (2)	0.99203 (17)	0.0229 (5)
H2A	0.109176	0.691275	1.011361	0.027*
H2B	0.346927	0.654494	1.046815	0.027*
C3	0.3150 (4)	0.8116 (2)	0.97588 (18)	0.0242 (5)
H3A	0.477316	0.812019	0.963476	0.029*
H3B	0.255830	0.848734	1.037476	0.029*
C4	0.2117 (4)	0.8776 (2)	0.88881 (17)	0.0197 (5)
C5	0.2829 (4)	0.81065 (18)	0.79513 (16)	0.0165 (5)
H5A	0.447652	0.807518	0.780592	0.020*
C6	0.1973 (4)	0.86853 (19)	0.70123 (17)	0.0204 (5)
H6A	0.036728	0.865182	0.706101	0.025*
H6B	0.217951	0.946753	0.695765	0.025*
C7	0.3208 (4)	0.8145 (2)	0.60876 (17)	0.0217 (5)
H7A	0.258907	0.852136	0.549816	0.026*
H7B	0.478688	0.824544	0.601016	0.026*
C8	0.3068 (4)	0.69224 (19)	0.61166 (16)	0.0195 (5)
C9	0.3730 (4)	0.63500 (18)	0.71134 (16)	0.0153 (4)
H9A	0.529908	0.647146	0.709885	0.018*
C10	0.2437 (4)	0.68813 (18)	0.80690 (16)	0.0152 (5)
C11	0.3847 (4)	0.50884 (18)	0.71485 (17)	0.0165 (5)
H11A	0.282256	0.483913	0.772988	0.020*
H11B	0.335633	0.489148	0.654297	0.020*
C12	0.6188 (4)	0.45017 (19)	0.72185 (16)	0.0167 (5)
H12A	0.662724	0.467844	0.784280	0.020*
H12B	0.720954	0.480076	0.666145	0.020*
C13	0.6511 (4)	0.32450 (19)	0.71953 (16)	0.0168 (5)
C14	0.8933 (4)	0.2823 (2)	0.7242 (2)	0.0250 (5)
H14A	0.945773	0.286512	0.785170	0.030*
C15	1.0374 (5)	0.2403 (2)	0.6516 (2)	0.0323 (6)
H15A	0.992358	0.234497	0.589297	0.039*
H15B	1.186820	0.215822	0.661295	0.039*
C16	0.5052 (4)	0.2701 (2)	0.80480 (17)	0.0230 (5)
H16A	0.348826	0.293799	0.797924	0.035*
H16B	0.533900	0.291423	0.868129	0.035*
H16C	0.539068	0.190152	0.803125	0.035*
C17	0.0848 (5)	0.6728 (2)	0.58652 (19)	0.0266 (5)
H17A	0.073983	0.698494	0.517120	0.040*
H17B	−0.036062	0.713207	0.629984	0.040*
H17C	0.073936	0.594183	0.596300	0.040*
C18	−0.0400 (4)	0.9065 (2)	0.91730 (19)	0.0261 (5)
H18A	−0.071381	0.952806	0.973438	0.039*
H18B	−0.105549	0.838908	0.936158	0.039*
H18C	−0.103815	0.946206	0.860520	0.039*
C19	0.3108 (5)	0.9856 (2)	0.86890 (19)	0.0273 (6)
H19A	0.231711	1.034786	0.821354	0.041*
H19B	0.468106	0.970019	0.841426	0.041*
H19C	0.295743	1.020728	0.931237	0.041*
C20	−0.0030 (4)	0.6716 (2)	0.82343 (17)	0.0195 (5)
H20A	−0.016327	0.601057	0.799861	0.029*
H20B	−0.088050	0.731123	0.786519	0.029*
H20C	−0.061023	0.672312	0.894385	0.029*
C21	0.7310 (5)	0.0149 (2)	0.6296 (2)	0.0316 (6)
H21A	0.787444	0.050837	0.679071	0.047*
H21B	0.850572	−0.003342	0.574925	0.047*
H21C	0.676596	−0.052475	0.660616	0.047*
H1	0.527 (7)	0.698 (4)	0.496 (3)	0.047*
H2	0.620 (7)	0.344 (4)	0.587 (3)	0.047*
H3	0.593 (7)	0.150 (4)	0.598 (3)	0.047*
O1'	0.6603 (3)	0.44467 (15)	0.46767 (12)	0.0212 (4)
O2'	0.5847 (3)	0.80229 (15)	0.37901 (13)	0.0233 (4)
O3'	0.4431 (4)	0.02360 (15)	0.42307 (15)	0.0315 (4)
C1'	0.8272 (4)	0.4748 (2)	0.10293 (16)	0.0178 (5)
H1'C	0.746711	0.549193	0.089278	0.021*
H1'D	0.969576	0.483180	0.123917	0.021*
C2'	0.8752 (4)	0.4148 (2)	0.00713 (17)	0.0225 (5)
H2'C	0.733849	0.411160	−0.017075	0.027*
H2'D	0.967042	0.456366	−0.044670	0.027*
C3'	0.9966 (4)	0.2986 (2)	0.02478 (17)	0.0221 (5)
H3'C	1.144075	0.303261	0.042423	0.027*
H3'D	1.020401	0.261636	−0.037815	0.027*
C4'	0.8720 (4)	0.2281 (2)	0.10727 (16)	0.0175 (5)
C5'	0.8070 (4)	0.29321 (19)	0.20155 (15)	0.0156 (5)
H5'B	0.951868	0.300536	0.222311	0.019*
C6'	0.6868 (4)	0.23040 (19)	0.29028 (16)	0.0188 (5)
H6'C	0.760689	0.153434	0.295796	0.023*
H6'D	0.531744	0.229759	0.280080	0.023*
C7'	0.6883 (4)	0.28425 (19)	0.38620 (16)	0.0195 (5)
H7'C	0.605665	0.243516	0.442155	0.023*
H7'D	0.843335	0.278028	0.398973	0.023*
C8'	0.5866 (4)	0.40447 (19)	0.38362 (15)	0.0173 (5)
C9'	0.6913 (4)	0.46712 (18)	0.28773 (16)	0.0153 (5)
H9'B	0.852132	0.460276	0.294146	0.018*
C10'	0.6878 (4)	0.41355 (19)	0.18894 (15)	0.0149 (5)
C11'	0.6089 (4)	0.59222 (19)	0.28424 (16)	0.0171 (5)
H11C	0.542379	0.615174	0.222839	0.021*
H11D	0.492239	0.608286	0.341618	0.021*
C12'	0.7963 (4)	0.65792 (19)	0.28669 (18)	0.0203 (5)
H12C	0.908418	0.643263	0.227409	0.024*
H12D	0.868165	0.630119	0.345828	0.024*
C13'	0.7316 (4)	0.78318 (19)	0.28935 (17)	0.0198 (5)
C14'	0.9418 (5)	0.8313 (2)	0.2854 (2)	0.0339 (6)
H14B	1.040294	0.829002	0.224462	0.041*
C15'	1.0016 (6)	0.8753 (3)	0.3560 (3)	0.0428 (7)
H15C	0.908853	0.879598	0.418333	0.051*
H15D	1.138537	0.903498	0.345856	0.051*
C16'	0.6126 (5)	0.8343 (2)	0.2011 (2)	0.0326 (6)
H16D	0.479166	0.800358	0.201777	0.049*
H16E	0.712266	0.821499	0.138778	0.049*
H16F	0.570633	0.913410	0.206831	0.049*
C17'	0.3332 (4)	0.4173 (2)	0.40188 (17)	0.0229 (5)
H17D	0.283551	0.386445	0.469007	0.034*
H17E	0.281417	0.378218	0.353152	0.034*
H17F	0.272408	0.495291	0.395170	0.034*
C18'	1.0347 (4)	0.1241 (2)	0.13027 (18)	0.0242 (5)
H18D	1.096705	0.089449	0.068545	0.036*
H18E	0.955905	0.072601	0.176329	0.036*
H18F	1.154937	0.144153	0.160549	0.036*
C19'	0.6731 (4)	0.1913 (2)	0.07099 (18)	0.0236 (5)
H19D	0.576523	0.255871	0.047117	0.035*
H19E	0.589350	0.151320	0.125986	0.035*
H19F	0.726912	0.143175	0.016803	0.035*
C20'	0.4479 (4)	0.4233 (2)	0.16401 (17)	0.0190 (5)
H20D	0.360754	0.491371	0.187734	0.028*
H20E	0.378987	0.360391	0.196612	0.028*
H20F	0.452926	0.424146	0.091969	0.028*
C21'	0.2414 (5)	0.0939 (3)	0.4111 (2)	0.0349 (6)
H21D	0.118965	0.066723	0.456538	0.052*
H21E	0.213118	0.094828	0.342464	0.052*
H21F	0.253422	0.168387	0.425907	0.052*
H1'	0.586 (7)	0.507 (4)	0.488 (3)	0.052*
H2'	0.564 (7)	0.862 (4)	0.391 (3)	0.052*
H3'	0.514 (7)	0.038 (4)	0.472 (3)	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0414 (10)	0.0174 (9)	0.0142 (8)	−0.0050 (8)	0.0070 (7)	−0.0023 (7)
O2	0.0235 (8)	0.0160 (8)	0.0129 (7)	−0.0058 (6)	−0.0050 (6)	−0.0015 (6)
O3	0.0511 (12)	0.0199 (10)	0.0393 (11)	−0.0047 (9)	−0.0177 (9)	−0.0021 (8)
C1	0.0202 (11)	0.0184 (12)	0.0194 (11)	−0.0038 (9)	−0.0013 (9)	−0.0024 (9)
C2	0.0288 (12)	0.0249 (14)	0.0149 (11)	−0.0047 (10)	−0.0032 (9)	−0.0002 (9)
C3	0.0304 (13)	0.0267 (14)	0.0166 (11)	−0.0072 (10)	0.0002 (9)	−0.0074 (9)
C4	0.0237 (12)	0.0162 (12)	0.0183 (11)	−0.0054 (9)	0.0045 (9)	−0.0047 (9)
C5	0.0170 (10)	0.0150 (12)	0.0170 (11)	−0.0036 (9)	0.0021 (8)	−0.0041 (9)
C6	0.0277 (12)	0.0134 (11)	0.0185 (11)	−0.0026 (9)	0.0016 (9)	−0.0011 (9)
C7	0.0321 (13)	0.0165 (12)	0.0150 (10)	−0.0047 (10)	0.0014 (9)	0.0000 (8)
C8	0.0280 (12)	0.0151 (12)	0.0146 (10)	−0.0040 (9)	0.0007 (9)	−0.0026 (8)
C9	0.0163 (10)	0.0135 (11)	0.0162 (11)	−0.0042 (8)	−0.0002 (8)	−0.0021 (8)
C10	0.0160 (10)	0.0150 (12)	0.0141 (10)	−0.0040 (9)	0.0009 (8)	−0.0009 (8)
C11	0.0197 (11)	0.0129 (12)	0.0175 (10)	−0.0055 (9)	−0.0008 (8)	−0.0016 (8)
C12	0.0181 (11)	0.0169 (12)	0.0165 (10)	−0.0055 (9)	−0.0032 (8)	−0.0032 (8)
C13	0.0208 (11)	0.0186 (12)	0.0127 (10)	−0.0033 (9)	−0.0058 (8)	−0.0035 (8)
C14	0.0249 (12)	0.0241 (13)	0.0284 (12)	−0.0012 (10)	−0.0124 (10)	−0.0036 (10)
C15	0.0232 (12)	0.0369 (16)	0.0384 (15)	−0.0015 (11)	−0.0074 (11)	−0.0102 (12)
C16	0.0341 (13)	0.0200 (12)	0.0158 (11)	−0.0074 (10)	−0.0037 (9)	0.0004 (9)
C17	0.0359 (14)	0.0229 (14)	0.0224 (12)	−0.0025 (11)	−0.0118 (10)	0.0001 (10)
C18	0.0260 (12)	0.0245 (13)	0.0254 (12)	−0.0019 (10)	0.0056 (10)	−0.0075 (10)
C19	0.0369 (14)	0.0220 (13)	0.0238 (12)	−0.0124 (11)	0.0061 (10)	−0.0094 (10)
C20	0.0186 (11)	0.0190 (12)	0.0209 (11)	−0.0044 (9)	−0.0004 (8)	−0.0021 (9)
C21	0.0343 (14)	0.0283 (15)	0.0334 (14)	−0.0091 (12)	−0.0052 (11)	−0.0009 (11)
O1'	0.0340 (9)	0.0178 (9)	0.0120 (7)	−0.0034 (7)	−0.0026 (6)	−0.0038 (6)
O2'	0.0325 (10)	0.0171 (9)	0.0199 (8)	−0.0084 (7)	0.0044 (7)	−0.0043 (7)
O3'	0.0474 (12)	0.0188 (10)	0.0290 (10)	−0.0037 (8)	−0.0078 (9)	−0.0034 (7)
C1'	0.0219 (11)	0.0194 (12)	0.0127 (10)	−0.0077 (9)	−0.0011 (8)	0.0017 (8)
C2'	0.0290 (12)	0.0247 (13)	0.0133 (10)	−0.0086 (10)	0.0013 (9)	0.0012 (9)
C3'	0.0279 (12)	0.0261 (14)	0.0119 (10)	−0.0066 (10)	0.0025 (9)	−0.0029 (9)
C4'	0.0222 (11)	0.0189 (12)	0.0113 (10)	−0.0049 (9)	0.0003 (8)	−0.0025 (8)
C5'	0.0198 (11)	0.0185 (12)	0.0097 (10)	−0.0058 (9)	−0.0019 (8)	−0.0020 (8)
C6'	0.0277 (12)	0.0146 (12)	0.0142 (10)	−0.0062 (9)	0.0001 (9)	−0.0023 (8)
C7'	0.0316 (13)	0.0161 (12)	0.0109 (10)	−0.0060 (10)	−0.0007 (9)	−0.0008 (8)
C8'	0.0235 (11)	0.0190 (12)	0.0100 (10)	−0.0072 (9)	0.0008 (8)	−0.0031 (8)
C9'	0.0180 (10)	0.0158 (12)	0.0121 (10)	−0.0042 (9)	−0.0010 (8)	−0.0009 (8)
C10'	0.0167 (10)	0.0177 (12)	0.0117 (10)	−0.0070 (9)	−0.0012 (8)	−0.0016 (8)
C11'	0.0219 (11)	0.0162 (12)	0.0130 (10)	−0.0039 (9)	−0.0001 (8)	−0.0022 (8)
C12'	0.0200 (11)	0.0162 (12)	0.0242 (12)	−0.0058 (9)	0.0005 (9)	−0.0010 (9)
C13'	0.0236 (11)	0.0172 (12)	0.0178 (11)	−0.0076 (9)	0.0029 (9)	0.0002 (8)
C14'	0.0295 (14)	0.0215 (14)	0.0508 (18)	−0.0123 (11)	0.0013 (12)	−0.0012 (12)
C15'	0.0358 (15)	0.0369 (18)	0.060 (2)	−0.0106 (13)	−0.0124 (14)	−0.0064 (14)
C16'	0.0524 (17)	0.0225 (14)	0.0240 (13)	−0.0079 (12)	−0.0074 (12)	0.0005 (10)
C17'	0.0238 (12)	0.0243 (13)	0.0194 (11)	−0.0081 (10)	0.0059 (9)	−0.0030 (9)
C18'	0.0302 (13)	0.0223 (13)	0.0184 (11)	0.0011 (10)	−0.0011 (9)	−0.0053 (9)
C19'	0.0327 (13)	0.0238 (13)	0.0173 (11)	−0.0101 (11)	−0.0038 (10)	−0.0057 (9)
C20'	0.0189 (11)	0.0206 (12)	0.0187 (10)	−0.0053 (9)	−0.0035 (8)	−0.0026 (8)
C21'	0.0336 (14)	0.0345 (17)	0.0362 (15)	−0.0092 (12)	−0.0007 (12)	−0.0013 (12)

Geometric parameters (Å, º) top

O1—C8	1.454 (3)	O1'—C8'	1.458 (3)
O1—H1	0.87 (4)	O1'—H1'	0.88 (5)
O2—C13	1.439 (3)	O2'—C13'	1.421 (3)
O2—H2	0.81 (5)	O2'—H2'	0.76 (5)
O3—C21	1.376 (4)	O3'—C21'	1.424 (4)
O3—H3	0.88 (4)	O3'—H3'	0.90 (5)
C1—C2	1.530 (3)	C1'—C2'	1.535 (3)
C1—C10	1.551 (3)	C1'—C10'	1.551 (3)
C1—H1A	0.9900	C1'—H1'C	0.9900
C1—H1B	0.9900	C1'—H1'D	0.9900
C2—C3	1.528 (4)	C2'—C3'	1.528 (4)
C2—H2A	0.9900	C2'—H2'C	0.9900
C2—H2B	0.9900	C2'—H2'D	0.9900
C3—C4	1.542 (4)	C3'—C4'	1.538 (3)
C3—H3A	0.9900	C3'—H3'C	0.9900
C3—H3B	0.9900	C3'—H3'D	0.9900
C4—C18	1.534 (3)	C4'—C18'	1.541 (4)
C4—C19	1.538 (3)	C4'—C19'	1.542 (3)
C4—C5	1.562 (3)	C4'—C5'	1.553 (3)
C5—C6	1.535 (3)	C5'—C6'	1.528 (3)
C5—C10	1.561 (3)	C5'—C10'	1.559 (3)
C5—H5A	1.0000	C5'—H5'B	1.0000
C6—C7	1.526 (3)	C6'—C7'	1.531 (3)
C6—H6A	0.9900	C6'—H6'C	0.9900
C6—H6B	0.9900	C6'—H6'D	0.9900
C7—C8	1.524 (3)	C7'—C8'	1.519 (3)
C7—H7A	0.9900	C7'—H7'C	0.9900
C7—H7B	0.9900	C7'—H7'D	0.9900
C8—C17	1.524 (4)	C8'—C17'	1.529 (3)
C8—C9	1.556 (3)	C8'—C9'	1.557 (3)
C9—C11	1.547 (3)	C9'—C11'	1.550 (3)
C9—C10	1.565 (3)	C9'—C10'	1.568 (3)
C9—H9A	1.0000	C9'—H9'B	1.0000
C10—C20	1.546 (3)	C10'—C20'	1.555 (3)
C11—C12	1.524 (3)	C11'—C12'	1.522 (3)
C11—H11A	0.9900	C11'—H11C	0.9900
C11—H11B	0.9900	C11'—H11D	0.9900
C12—C13	1.539 (3)	C12'—C13'	1.541 (3)
C12—H12A	0.9900	C12'—H12C	0.9900
C12—H12B	0.9900	C12'—H12D	0.9900
C13—C14	1.513 (3)	C13'—C14'	1.502 (3)
C13—C16	1.525 (3)	C13'—C16'	1.543 (4)
C14—C15	1.313 (4)	C14'—C15'	1.283 (5)
C14—H14A	0.9500	C14'—H14B	0.9500
C15—H15A	0.9500	C15'—H15C	0.9500
C15—H15B	0.9500	C15'—H15D	0.9500
C16—H16A	0.9800	C16'—H16D	0.9800
C16—H16B	0.9800	C16'—H16E	0.9800
C16—H16C	0.9800	C16'—H16F	0.9800
C17—H17A	0.9800	C17'—H17D	0.9800
C17—H17B	0.9800	C17'—H17E	0.9800
C17—H17C	0.9800	C17'—H17F	0.9800
C18—H18A	0.9800	C18'—H18D	0.9800
C18—H18B	0.9800	C18'—H18E	0.9800
C18—H18C	0.9800	C18'—H18F	0.9800
C19—H19A	0.9800	C19'—H19D	0.9800
C19—H19B	0.9800	C19'—H19E	0.9800
C19—H19C	0.9800	C19'—H19F	0.9800
C20—H20A	0.9800	C20'—H20D	0.9800
C20—H20B	0.9800	C20'—H20E	0.9800
C20—H20C	0.9800	C20'—H20F	0.9800
C21—H21A	0.9800	C21'—H21D	0.9800
C21—H21B	0.9800	C21'—H21E	0.9800
C21—H21C	0.9800	C21'—H21F	0.9800

C8—O1—H1	109 (3)	C8'—O1'—H1'	116 (3)
C13—O2—H2	106 (3)	C13'—O2'—H2'	113 (3)
C21—O3—H3	104 (3)	C21'—O3'—H3'	116 (3)
C2—C1—C10	113.11 (19)	C2'—C1'—C10'	112.77 (19)
C2—C1—H1A	109.0	C2'—C1'—H1'C	109.0
C10—C1—H1A	109.0	C10'—C1'—H1'C	109.0
C2—C1—H1B	109.0	C2'—C1'—H1'D	109.0
C10—C1—H1B	109.0	C10'—C1'—H1'D	109.0
H1A—C1—H1B	107.8	H1'C—C1'—H1'D	107.8
C3—C2—C1	110.86 (19)	C3'—C2'—C1'	111.04 (19)
C3—C2—H2A	109.5	C3'—C2'—H2'C	109.4
C1—C2—H2A	109.5	C1'—C2'—H2'C	109.4
C3—C2—H2B	109.5	C3'—C2'—H2'D	109.4
C1—C2—H2B	109.5	C1'—C2'—H2'D	109.4
H2A—C2—H2B	108.1	H2'C—C2'—H2'D	108.0
C2—C3—C4	113.9 (2)	C2'—C3'—C4'	113.7 (2)
C2—C3—H3A	108.8	C2'—C3'—H3'C	108.8
C4—C3—H3A	108.8	C4'—C3'—H3'C	108.8
C2—C3—H3B	108.8	C2'—C3'—H3'D	108.8
C4—C3—H3B	108.8	C4'—C3'—H3'D	108.8
H3A—C3—H3B	107.7	H3'C—C3'—H3'D	107.7
C18—C4—C19	107.9 (2)	C3'—C4'—C18'	107.01 (19)
C18—C4—C3	110.5 (2)	C3'—C4'—C19'	110.70 (18)
C19—C4—C3	107.2 (2)	C18'—C4'—C19'	107.6 (2)
C18—C4—C5	114.3 (2)	C3'—C4'—C5'	108.73 (18)
C19—C4—C5	108.63 (18)	C18'—C4'—C5'	108.96 (18)
C3—C4—C5	108.15 (19)	C19'—C4'—C5'	113.63 (19)
C6—C5—C10	110.12 (18)	C6'—C5'—C4'	113.84 (18)
C6—C5—C4	113.92 (19)	C6'—C5'—C10'	110.47 (18)
C10—C5—C4	117.09 (17)	C4'—C5'—C10'	117.57 (17)
C6—C5—H5A	104.8	C6'—C5'—H5'B	104.5
C10—C5—H5A	104.8	C4'—C5'—H5'B	104.5
C4—C5—H5A	104.8	C10'—C5'—H5'B	104.5
C7—C6—C5	110.79 (19)	C5'—C6'—C7'	110.36 (18)
C7—C6—H6A	109.5	C5'—C6'—H6'C	109.6
C5—C6—H6A	109.5	C7'—C6'—H6'C	109.6
C7—C6—H6B	109.5	C5'—C6'—H6'D	109.6
C5—C6—H6B	109.5	C7'—C6'—H6'D	109.6
H6A—C6—H6B	108.1	H6'C—C6'—H6'D	108.1
C8—C7—C6	113.62 (18)	C8'—C7'—C6'	113.70 (19)
C8—C7—H7A	108.8	C8'—C7'—H7'C	108.8
C6—C7—H7A	108.8	C6'—C7'—H7'C	108.8
C8—C7—H7B	108.8	C8'—C7'—H7'D	108.8
C6—C7—H7B	108.8	C6'—C7'—H7'D	108.8
H7A—C7—H7B	107.7	H7'C—C7'—H7'D	107.7
O1—C8—C17	107.19 (19)	O1'—C8'—C7'	103.63 (18)
O1—C8—C7	107.78 (18)	O1'—C8'—C17'	108.14 (18)
C17—C8—C7	111.3 (2)	C7'—C8'—C17'	111.31 (19)
O1—C8—C9	104.60 (18)	O1'—C8'—C9'	107.29 (17)
C17—C8—C9	116.24 (19)	C7'—C8'—C9'	109.75 (18)
C7—C8—C9	109.14 (19)	C17'—C8'—C9'	115.90 (19)
C11—C9—C8	111.82 (18)	C11'—C9'—C8'	112.55 (18)
C11—C9—C10	114.56 (18)	C11'—C9'—C10'	114.24 (17)
C8—C9—C10	115.04 (18)	C8'—C9'—C10'	114.75 (17)
C11—C9—H9A	104.7	C11'—C9'—H9'B	104.6
C8—C9—H9A	104.7	C8'—C9'—H9'B	104.6
C10—C9—H9A	104.7	C10'—C9'—H9'B	104.6
C20—C10—C1	108.67 (17)	C1'—C10'—C20'	108.17 (18)
C20—C10—C5	114.51 (18)	C1'—C10'—C5'	107.80 (18)
C1—C10—C5	107.27 (17)	C20'—C10'—C5'	114.18 (18)
C20—C10—C9	111.51 (18)	C1'—C10'—C9'	108.48 (17)
C1—C10—C9	108.40 (18)	C20'—C10'—C9'	111.51 (18)
C5—C10—C9	106.25 (16)	C5'—C10'—C9'	106.53 (16)
C12—C11—C9	111.66 (18)	C12'—C11'—C9'	111.79 (19)
C12—C11—H11A	109.3	C12'—C11'—H11C	109.3
C9—C11—H11A	109.3	C9'—C11'—H11C	109.3
C12—C11—H11B	109.3	C12'—C11'—H11D	109.3
C9—C11—H11B	109.3	C9'—C11'—H11D	109.3
H11A—C11—H11B	107.9	H11C—C11'—H11D	107.9
C11—C12—C13	115.76 (18)	C11'—C12'—C13'	116.4 (2)
C11—C12—H12A	108.3	C11'—C12'—H12C	108.2
C13—C12—H12A	108.3	C13'—C12'—H12C	108.2
C11—C12—H12B	108.3	C11'—C12'—H12D	108.2
C13—C12—H12B	108.3	C13'—C12'—H12D	108.2
H12A—C12—H12B	107.4	H12C—C12'—H12D	107.3
O2—C13—C14	110.35 (19)	O2'—C13'—C14'	112.2 (2)
O2—C13—C16	106.17 (17)	O2'—C13'—C12'	107.08 (18)
C14—C13—C16	110.3 (2)	C14'—C13'—C12'	107.3 (2)
O2—C13—C12	109.85 (17)	O2'—C13'—C16'	108.7 (2)
C14—C13—C12	107.79 (19)	C14'—C13'—C16'	109.4 (2)
C16—C13—C12	112.37 (19)	C12'—C13'—C16'	112.2 (2)
C15—C14—C13	125.8 (2)	C15'—C14'—C13'	126.5 (3)
C15—C14—H14A	117.1	C15'—C14'—H14B	116.7
C13—C14—H14A	117.1	C13'—C14'—H14B	116.7
C14—C15—H15A	120.0	C14'—C15'—H15C	120.0
C14—C15—H15B	120.0	C14'—C15'—H15D	120.0
H15A—C15—H15B	120.0	H15C—C15'—H15D	120.0
C13—C16—H16A	109.5	C13'—C16'—H16D	109.5
C13—C16—H16B	109.5	C13'—C16'—H16E	109.5
H16A—C16—H16B	109.5	H16D—C16'—H16E	109.5
C13—C16—H16C	109.5	C13'—C16'—H16F	109.5
H16A—C16—H16C	109.5	H16D—C16'—H16F	109.5
H16B—C16—H16C	109.5	H16E—C16'—H16F	109.5
C8—C17—H17A	109.5	C8'—C17'—H17D	109.5
C8—C17—H17B	109.5	C8'—C17'—H17E	109.5
H17A—C17—H17B	109.5	H17D—C17'—H17E	109.5
C8—C17—H17C	109.5	C8'—C17'—H17F	109.5
H17A—C17—H17C	109.5	H17D—C17'—H17F	109.5
H17B—C17—H17C	109.5	H17E—C17'—H17F	109.5
C4—C18—H18A	109.5	C4'—C18'—H18D	109.5
C4—C18—H18B	109.5	C4'—C18'—H18E	109.5
H18A—C18—H18B	109.5	H18D—C18'—H18E	109.5
C4—C18—H18C	109.5	C4'—C18'—H18F	109.5
H18A—C18—H18C	109.5	H18D—C18'—H18F	109.5
H18B—C18—H18C	109.5	H18E—C18'—H18F	109.5
C4—C19—H19A	109.5	C4'—C19'—H19D	109.5
C4—C19—H19B	109.5	C4'—C19'—H19E	109.5
H19A—C19—H19B	109.5	H19D—C19'—H19E	109.5
C4—C19—H19C	109.5	C4'—C19'—H19F	109.5
H19A—C19—H19C	109.5	H19D—C19'—H19F	109.5
H19B—C19—H19C	109.5	H19E—C19'—H19F	109.5
C10—C20—H20A	109.5	C10'—C20'—H20D	109.5
C10—C20—H20B	109.5	C10'—C20'—H20E	109.5
H20A—C20—H20B	109.5	H20D—C20'—H20E	109.5
C10—C20—H20C	109.5	C10'—C20'—H20F	109.5
H20A—C20—H20C	109.5	H20D—C20'—H20F	109.5
H20B—C20—H20C	109.5	H20E—C20'—H20F	109.5
O3—C21—H21A	109.5	O3'—C21'—H21D	109.5
O3—C21—H21B	109.5	O3'—C21'—H21E	109.5
H21A—C21—H21B	109.5	H21D—C21'—H21E	109.5
O3—C21—H21C	109.5	O3'—C21'—H21F	109.5
H21A—C21—H21C	109.5	H21D—C21'—H21F	109.5
H21B—C21—H21C	109.5	H21E—C21'—H21F	109.5

C10—C1—C2—C3	−58.0 (3)	C10'—C1'—C2'—C3'	−57.9 (3)
C1—C2—C3—C4	56.6 (3)	C1'—C2'—C3'—C4'	56.7 (3)
C2—C3—C4—C18	74.2 (3)	C2'—C3'—C4'—C18'	−168.60 (19)
C2—C3—C4—C19	−168.4 (2)	C2'—C3'—C4'—C19'	74.4 (3)
C2—C3—C4—C5	−51.5 (3)	C2'—C3'—C4'—C5'	−51.0 (3)
C18—C4—C5—C6	58.4 (3)	C3'—C4'—C5'—C6'	−178.50 (19)
C19—C4—C5—C6	−62.2 (3)	C18'—C4'—C5'—C6'	−62.2 (2)
C3—C4—C5—C6	−178.2 (2)	C19'—C4'—C5'—C6'	57.7 (3)
C18—C4—C5—C10	−72.1 (3)	C3'—C4'—C5'—C10'	50.1 (2)
C19—C4—C5—C10	167.3 (2)	C18'—C4'—C5'—C10'	166.36 (19)
C3—C4—C5—C10	51.3 (3)	C19'—C4'—C5'—C10'	−73.7 (3)
C10—C5—C6—C7	−61.2 (2)	C4'—C5'—C6'—C7'	163.7 (2)
C4—C5—C6—C7	164.94 (19)	C10'—C5'—C6'—C7'	−61.4 (2)
C5—C6—C7—C8	56.9 (3)	C5'—C6'—C7'—C8'	56.8 (3)
C6—C7—C8—O1	−163.9 (2)	C6'—C7'—C8'—O1'	−164.87 (18)
C6—C7—C8—C17	78.8 (3)	C6'—C7'—C8'—C17'	79.1 (2)
C6—C7—C8—C9	−50.8 (3)	C6'—C7'—C8'—C9'	−50.5 (3)
O1—C8—C9—C11	−59.3 (2)	O1'—C8'—C9'—C11'	−63.5 (2)
C17—C8—C9—C11	58.7 (3)	C7'—C8'—C9'—C11'	−175.43 (19)
C7—C8—C9—C11	−174.42 (19)	C17'—C8'—C9'—C11'	57.4 (3)
O1—C8—C9—C10	167.77 (17)	O1'—C8'—C9'—C10'	163.62 (18)
C17—C8—C9—C10	−74.3 (3)	C7'—C8'—C9'—C10'	51.7 (2)
C7—C8—C9—C10	52.6 (2)	C17'—C8'—C9'—C10'	−75.5 (3)
C2—C1—C10—C20	−70.2 (2)	C2'—C1'—C10'—C20'	−70.8 (2)
C2—C1—C10—C5	54.1 (2)	C2'—C1'—C10'—C5'	53.2 (2)
C2—C1—C10—C9	168.48 (18)	C2'—C1'—C10'—C9'	168.13 (19)
C6—C5—C10—C20	−64.1 (2)	C6'—C5'—C10'—C1'	175.93 (17)
C4—C5—C10—C20	68.2 (3)	C4'—C5'—C10'—C1'	−51.1 (2)
C6—C5—C10—C1	175.24 (18)	C6'—C5'—C10'—C20'	−63.9 (2)
C4—C5—C10—C1	−52.5 (2)	C4'—C5'—C10'—C20'	69.1 (2)
C6—C5—C10—C9	59.5 (2)	C6'—C5'—C10'—C9'	59.7 (2)
C4—C5—C10—C9	−168.29 (18)	C4'—C5'—C10'—C9'	−167.37 (17)
C11—C9—C10—C20	−63.2 (2)	C11'—C9'—C10'—C1'	56.2 (2)
C8—C9—C10—C20	68.4 (2)	C8'—C9'—C10'—C1'	−171.73 (19)
C11—C9—C10—C1	56.4 (2)	C11'—C9'—C10'—C20'	−62.9 (2)
C8—C9—C10—C1	−171.97 (18)	C8'—C9'—C10'—C20'	69.2 (2)
C11—C9—C10—C5	171.39 (18)	C11'—C9'—C10'—C5'	171.96 (17)
C8—C9—C10—C5	−57.0 (2)	C8'—C9'—C10'—C5'	−55.9 (2)
C8—C9—C11—C12	116.6 (2)	C8'—C9'—C11'—C12'	115.7 (2)
C10—C9—C11—C12	−110.2 (2)	C10'—C9'—C11'—C12'	−111.2 (2)
C9—C11—C12—C13	−176.52 (17)	C9'—C11'—C12'—C13'	−176.76 (18)
C11—C12—C13—O2	58.1 (2)	C11'—C12'—C13'—O2'	62.6 (3)
C11—C12—C13—C14	178.38 (19)	C11'—C12'—C13'—C14'	−176.7 (2)
C11—C12—C13—C16	−59.8 (2)	C11'—C12'—C13'—C16'	−56.6 (3)
O2—C13—C14—C15	9.7 (4)	O2'—C13'—C14'—C15'	7.0 (4)
C16—C13—C14—C15	126.8 (3)	C12'—C13'—C14'—C15'	−110.4 (3)
C12—C13—C14—C15	−110.2 (3)	C16'—C13'—C14'—C15'	127.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2′	0.87 (4)	1.97 (4)	2.816 (2)	163 (4)
O2—H2···O1′	0.81 (5)	1.96 (5)	2.762 (2)	167 (4)
O3—H3···O2	0.88 (4)	1.89 (5)	2.744 (3)	164 (4)
O1′—H1′···O1	0.88 (5)	1.87 (5)	2.744 (2)	170 (4)
O2′—H2′···O3′ⁱ	0.76 (5)	2.08 (5)	2.833 (3)	169 (5)
O3′—H3′···O3	0.90 (5)	1.89 (5)	2.753 (3)	160 (4)

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

Funding information

The research leading to these results has, in part, received funding from UK Research and Innovation via the Global Challenges Research Fund under grant agreement `A Global Network for Neglected Tropical Diseases', grant No. MR/P027989/1.

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Volume 76| Part 3| March 2020| Pages 294-297

https://doi.org/10.1107/S2056989020001474

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research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure and Hirshfeld surface analysis of the methanol solvate of sclareol, a labdane-type diterpenoid

1. Chemical context

2. Structural commentary

3. Supra­molecular features and Hirshfeld surface analysis

4. In vitro anti-leishmanial activity

5. Database survey

6. Crystallization

7. Refinement

Supporting information

Funding information

References

research communications

3. Supramolecular features and Hirshfeld surface analysis