Form (III) of artemisinin: discovery and crystallographic characterization of a new high-pressure polymorph

Fetah, B.; Connor, L.E.; Warren, M.R.; Doherty, C.L.; Oswald, I.D.H.

doi:10.1107/S205252062600291X

research papers

STRUCTURAL SCIENCE
CRYSTAL ENGINEERING
MATERIALS

ISSN: 2052-5206

Volume 82| Part 3| June 2026| Pages 316-329

https://doi.org/10.1107/S205252062600291X

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Form (III) of artemisinin: discovery and crystallographic characterization of a new high-pressure polymorph

Banaz Fetah,^a Lauren E. Connor,^a,^b Mark R. Warren,^c Cheryl L. Doherty ^d and Iain D. H. Oswald ^a ^*

^aStrathclyde Institute of Pharmacy & Biomedical Sciences (SIPBS), University of Strathclyde, 161 Cathedral Street, Glasgow, G4 0RE, UK, ^bBiomedical Research, Novartis, Basel, 4002, Switzerland, ^cDiamond Light Source, Harwell Science and Innovation Campus, Chilton, Didcot, OX11 0DE, UK, and ^dMaterial Science, GlaxoSmithKline, Gunnels Wood Rd, Stevenage, SG1 2NY, UK
^*Correspondence e-mail: [email protected]

Edited by A. Nangia, CSIR–National Chemical Laboratory, India (Received 7 November 2025; accepted 19 March 2026; online 11 May 2026)

Artemisinin (ART) is mainly used for the treatment of malaria and exhibits polymorphism with two known crystalline forms. In this study, the high-pressure behaviour of these two polymorphs was investigated to evaluate their compressibility and identify if any pressure-induced phase transitions occur with a view to assessing the impact of manufacturing pressure on the active pharmaceutical ingredient. Form (I), the orthorhombic polymorph, is found to be the most compressible of the three. Form (II), a triclinic phase, undergoes a phase transition to a new polymorph that is observed at different pressures depending on the pressure-transmitting medium (PTM) used. The transition to form (III) occurs at 0.75 GPa when compressed in petroleum ether, however, this transition is delayed to 2.02 GPa in silicone oil. This highlights the influence of the PTM on the stability of the crystal structure. The newly characterized form (III) shares structural similarities with form (II) but differs in symmetry where a pseudo-2₁ screw axis in form (II) becomes a formal 2₁ screw axis in form (III), resulting in a change from triclinic to monoclinic and a reduction of the asymmetric unit from Z′ = 4 to Z′ = 2. These findings contribute to a deeper understanding of pressure-induced polymorphism in ART and underscore the importance of external factors, such as PTM, in influencing solid-state transitions relevant to pharmaceutical processing and formulation.

Keywords: diamond anvil cell (DAC); high pressure; polymorphism; single crystal; XRPD; artemisinin; compression-induced transformation.

CCDC references: 2465849; 2465850; 2465851; 2465852; 2465853; 2465854; 2465855; 2465856

1. Introduction

It is common to formulate active pharmaceutical ingredients (APIs) in the solid state for oral administration due to the non-invasive nature of this delivery route, stability of API and relative ease of production (Alqahtani et al., 2021 ). The identification of a solid form of the API with suitable properties and behaviours for this route of delivery is essential in the development of a successful drug product (Ticehurst & Marziano, 2015 ). Polymorphism, the ability of a molecule to exist in more than one crystalline form, can impact these physical properties by altering the free energy of the solid through changes in the molecular packing and intermolecular interactions (Bellur Atici & Karlığa, 2015 ; Bernstein, 2011 ). These changes impact the physicochemical properties of the polymorph when compared with the original form, potentially altering solubility and mechanical properties and impacting its processibility and efficacy (Censi & Di Martino, 2015 ). Therefore, if two polymorphs of the same compound exhibit different solubilities, then the bioavailability of the polymorphs may vary, which can have significant consequences for the accurate administration of the appropriate dosage to the patient. The antibiotic chloramphenicol palmitate is a good example to highlight the impact of polymorphism on bioavailability. The polymorphic forms of chloramphenicol palmitate include polymorph A (stable), polymorph B (metastable) (Eguchi & Iitaka, 1974 ) and polymorph C (unstable). Gamberini et al. (2006 ) used a combination of X-ray diffraction, spectroscopic techniques and thermal methods to differentiate between the three different forms. The authors were able to use specific wavelength ranges in the Raman spectra (413–435 and 1035–1158 cm⁻¹) to establish a linear relationship between the quantity of polymorph A in 2–14% mixtures of A and B polymorphs. Polymorph A is the thermodynamically stable form and is the inactive form of chloramphenicol palmitate, whilst polymorph B is the active form and is much more soluble, leading to an increase in dissolution rate. Aguiar et al. (1967 ) found a significant increase in the peak serum levels if form B was used compared with form A (22 µg ml⁻¹ for form B compared with 3 µg ml⁻¹ for form A). This is a significant change in the bioavailability of chloramphenicol palmitate and highlights the importance of control of the polymorphic forms. The extent of polymorphism in pharmaceutical materials has been captured by Cruz-Cabeza et al. (2015 ), showing that more than 50% of small organic molecules exhibit polymorphism. Cruz-Cabeza et al. (2015) investigated the difference in observed polymorphism in the Cambridge Structural Database (CSD) with respect to those found in industry databases. They found that polymorphism occurs in 37% of single-component materials in the CSD, rising to 53% and 66% in the Roche and Lilly databases, respectively. This increase is at least partly due to the pharmaceutical companies specifically conducting polymorphic screening during the early stages of drug development as it is critical to identify all possible solid forms to ensure drug stability and to facilitate the development of drug products to the satifaction of regulatory agencies. These agencies require strict controls on solid form across batches to ensure consistency of action and a detailed understanding of the solid form landscape under processing and manufacturing conditions (Kestur et al., 2023 ).

An area of increased research activity is the monitoring of polymorphism during tabletting. Under tabletting conditions, powders can experience pressures up to 300 MPa, which has been shown to promote transitions to other polymorphs during processing (Thakral et al., 2019 ; Park et al., 2022 ; Wildfong et al., 2007 ; Rogers et al., 2013 ). Analysis of tabletted forms was explored in chloramphenicol palmitate by Lin et al. (2006 ), who used it as a test subject to explore multivariate methods on Raman data for polymorphic identification in both a free powder and a processed tabletted form. Whilst this method development study investigated pre-set mixtures of polymorphs, other studies have indicated that changes to polymorphic forms under compression can occur. Form B of famotidine has been shown to be unstable to compression with conversion to form A (Roux et al., 2002 ; Német et al., 2005 ; Lin, 2014 ; Upadhyay et al., 2022 ). Otsuka et al., (1989 ) and Thakral et al. (2019) investigated polymorphic transitions in chlorpropamide on tabletting. Thakral et al., (2019) showed that conversion between form A (α) to form C (γ) occurs and is dependent on the position within the tablet. The percentage conversion was observed to be higher at the edges of the tablet than in the centre. The spatial dependence suggests a link to localized variations in pressure during compaction; however, the impact of heat cannot be ruled out as a route of polymorphic conversion (Zavaliangos et al., 2008 ). In fact, Boldyreva et al. (2006 ) did not observe the transition in chlorpropamide in a diamond anvil cell (DAC), stating that local heating effects are likely to be the cause of the transition. The previous work involved the destructive analysis of discrete tablet sections. In contrast, Gasol-Cardona et al. (2025b ) employed X-ray diffraction computed tomography to analyse glycolide tablets non-destructively, detecting the presence of a high-pressure phase at compaction pressures as low as 250 MPa. Furthermore, work by Kakde et al. (2025 ) explored the use of DACs as part of a polymorph screening protocol. They investigated hydrochlorothiazide using a combination of texture analyser (TA) and DAC techniques to reveal that phase transitions occurring in the DAC at 500 MPa also appeared under tabletting conditions in the TA at 300 MPa. Collectively, the materials used in the latter studies have been investigated using both DAC (to reveal structure) and manufacturing processes (to reveal the impact of the process) and highlights the potential of DAC studies to simulate pressure-induced phase transitions relevant to pharmaceutical tabletting.

Building on these findings, this study focuses on the solid-state behaviour of a pharmaceutically relevant compound under high pressure. Artemisinin (ART) (see Scheme 1) is a sesquiterpene lactone with an endoperoxide 1,2,4-trioxane ring.

ART is used for treating malaria and derived from sweet wormwood extracts. ART exhibits two observable crystalline forms under ambient-temperature conditions; orthorhombic form (I) and triclinic form (II) which have been previously identified and their crystal structures determined (Lisgarten et al., 1998

; Chan et al., 1997

). Further co-crystals with orcinol and resorcinol have been identified via mechanochemical methods and their structures characterized (Karki et al., 2010

). The orthorhombic form is thermodynamically stable at low temperatures, whereas the triclinic form is stable at higher temperatures with the two polymorphs being enantiotropically related (Horosanskaia et al., 2014

). The phase transition was determined to be at 130°C using differential scanning calorimetry and temperature-resolved X-ray diffraction (Horosanskaia et al., 2014

). Form (II) is observed over the entire temperature range (to 147°C; melting point 153°C) and on cooling to ambient temperature showing its resistance to transformation. To date, the response of ART to pressure is unknown. Given that pressure plays a crucial role in manufacturing processes and that high-pressure polymorphs have been observed in tablets, we investigated the behaviour of the known polymorphs of ART under high-pressure conditions to evaluate its structural stability and determine whether a pressure-induced phase transition could be observed.

2. Materials and methods

2.1. Materials

ART was purchased from Alfa Aesar. The solvents used were ethanol (99.8%) purchased from Fisher and cyclohexane (≥99.0%) purchased from Sigma Aldrich.

2.2. Method of preparation for recrystallization

To obtain crystals of form (II) of ART, ART was slurried in cyclohexane (1 g ml⁻¹) using two magnetic stirrers at 340 rpm and ∼293 K for 24 h. To obtain single crystals for analysis, the supernatant solution was filtered through a pre-soaked 0.2 µm PTFE filter into a different glass vial. The glass vial was covered with aluminium foil and perforated for slow evaporation of the solvent at ∼293 K to obtain single crystals.

2.3. High-pressure DAC

A Merrill–Bassett DAC with a half-opening angle of 40° was used to apply pressure to single crystals of ART. The two diamonds with 600 µm culets were secured in tungsten carbide backing seats. A 250 µm-thick gasket, which functions as the sample chamber for the DAC, was drilled with a 200 µm or 300 µm tungsten carbide drill using the Almax Easylab Driller. A ruby chip was added to the sample chamber along with petroleum ether [pressure-transmitting medium (PTM)] for hydrostatic compression. The pressure was determined using the ruby fluorescence technique (Shen et al., 2020 ; Forman et al., 1972 ).

2.3.1. High-pressure annealing

A similar set-up was used for the annealing process to grow better crystals of the triclinic phase. In this case, the supersaturated cyclohexane solution of ART was used as solvent to anneal the crystal. The DAC was heat cycled around ∼130°C to form the single crystal. After cooling, the crystal was subsequently loaded into a separate DAC and petroleum ether was used as the PTM to perform the compression study.

2.4. Sapphire capillary cell (SCC)

Data were collected using the high-pressure sapphire capillary cell for single crystals from 30 bar (0.003 GPa) up to 1200 bar (0.12 GPa) in Hutch 2 on beamline I19 at Diamond Light Source (McMonagle et al., 2020 ). Radiation of wavelength 0.48590 Å was used, with beam size of 100 µm × 100 µm in both horizontal and vertical directions. Data collection employed a Newport four-circle kappa goniometer and a DECTRIS Eiger2 4M CdTe detector. Crystal centering and acquisition was controlled using DLS's in-house GDA (Diamond Light Source, 2003 ) software. Data were collected following a standard strategy optimized for the sapphire capillary cell using a φ scan from −170 to 175° at a step size of 0.2° for 0.2 s exposure. Reduction was performed using xia2 (Winter, 2010 ) with DIALS (Diffraction Integration for Advanced Light Sources; Waterman et al., 2013 ) and CrysAlisPro (Rigaku Oxford Diffraction, 2015 ) to achieve optimal integrated intensities. This process included integration, absorption correction and space-group determination. Samples were measured across a pressure range of 0.002 GPa to 0.12 GPa).

The original sapphire capillary cell method involved using a carbon fibre tube; however, this method was altered to use thin Kapton film with small notches cut out of the film to aid the centring of the sample in the cell due to the poor visualization of the crystal in the cell (Gasol-Cardona et al., 2025a ). Single crystals of ART in cyclohexane were loaded onto the Kapton film near the notches to aid alignment.

2.5. Single-crystal X-ray diffraction (SC-XRD)

A Bruker D8 Venture diffractometer (Cu Kα1, λ = 1.54043 Å) with a PHOTON II detector was used to collect at 296 K and its ambient pressure X-ray data. Data were indexed and integrated using SAINT (Bruker, 2016 ), which is included in the APEX4 (Bruker, 2016) software. SADABS (Krause et al., 2015 ) was used for applying the absorption correction. The crystal structure refinements were conducted with SHELXL (Sheldrick, 2015a ) via Olex2-1.5 (Dolomanov et al., 2009 ) using the coordinates of form (I), collected from the CSD (ref code: QNGHSU). The refined atomic coordinates at each pressure were used as the input for each of the following datasets.

High-pressure data were collected on two instruments. Firstly, a Bruker APEX-II diffractometer with Incoatec IμS microfocus X-ray source (Mo Kα1, λ = 0.71073 Å) and a CCD detector was used for the collection of data for ART form (I). The data for the subsequent studies of ART form (II) and form (III) were collected on a Bruker D8 Venture diffractometer with IμS microfocus X-ray source (Mo Kα1, λ = 0.71073 Å) and a PHOTON II detector. Data were indexed and integrated using SAINT (Bruker, 2016), which is included in APEX4 (Bruker, 2016) software. SADABS (Krause et al., 2015) was used for applying the absorption correction. The structures were refined in Olex2-1.5 (Dolomanov et al., 2009). Non-hydrogen atoms were assigned anisotropic displacement parameters. The Flack parameter refined as part of the crystal structure refinements are meaningless due to a combination of the radiation used and the atoms in the molecule. To access a larger portion of reciprocal space, Mo radiation was used; hence, the absolute structure could not be determined. A Mogul geometry check was carried out in Mercury for bond length, ring, and torsion angle abnormalities and valence angle and distance restraints were applied to the high-pressure structures based on the output. The triclinic dataset [form (II)] was refined using CX-ASAP (Thompson et al., 2023 ). This program enables sequential refinement of crystal structures from a series of experimental data points (temperature/pressure) using SHELXL as the refinement package. The crystal structure refinement details for form (I) can be found in Table 1 and those of form (II) and (III) can be found in Table 2. The data points for the 0.75 GPa collection in petroleum ether and the 2.02 GPa collection in silicone oil were only sufficient to obtain unit-cell parameters. The data for these collections are found at the Zenodo website cited in the data availability statement.

Table 1
Experimental details

For all structures: C₁₅H₂₂O₅, M_r = 282.32, orthorhombic, P2₁2₁2₁, Z = 4, crystal size (mm) 0.25 × 0.18 × 0.09. Experiments were carried out at 296 K with Mo Kα radiation using a Bruker APEX-II CCD. Absorption was corrected for by multi-scan methods (SADABS; Krause et al., 2015). Refinement was on 184 parameters with 206 restraints. H-atom parameters were constrained.

	Form (I_1)	Form (I_2)	Form (I_3)	Form (I_4)
Crystal data
Pressure (GPa)	0.3	1.26	1.87	2.56
PTM	Petroleum ether	Petroleum ether	Petroleum ether	Petroleum ether
a, b, c (Å)	6.2555 (4), 9.1513 (6), 23.860 (4)	6.1207 (4), 8.9193 (6), 23.311 (4)	6.0650 (4), 8.8429 (6), 23.048 (4)	6.0225 (4), 8.7906 (6), 22.807 (4)
V (Å³)	1365.9 (3)	1272.6 (2)	1236.1 (2)	1207.5 (3)
μ (mm⁻¹)	0.10	0.11	0.11	0.12

Data collection
T_min, T_max	0.667, 0.745	0.639, 0.745	0.644, 0.745	0.635, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	5881, 748, 658	5140, 779, 665	5447, 747, 664	5183, 749, 652
R_int	0.047	0.045	0.044	0.050
θ_max (°)	23.3	23.3	23.2	23.2
(sin θ/λ)max (Å⁻¹)	0.556	0.555	0.555	0.555

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.122, 1.12	0.054, 0.182, 1.16	0.032, 0.071, 1.12	0.042, 0.116, 1.18
No. of reflections	748	779	747	749
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.14	0.41, −0.36	0.12, −0.12	0.20, −0.22
Absolute structure	Flack x determined using 237 quotients [(I⁺) − (I⁻)]/[(I⁺) + (I⁻)] (Parsons et al., 2013 )	Flack x determined using 234 quotients [(I⁺) − (I⁻)]/[(I⁺) + (I⁻)] (Parsons et al., 2013)	Flack x determined using 238 quotients [(I⁺) − (I⁻)]/[(I⁺) + (I⁻)] (Parsons et al., 2013)	Flack x determined using 217 quotients [(I⁺) − (I⁻)]/[(I⁺) + (I⁻)] (Parsons et al., 2013)
Absolute structure parameter	0.5 (8)	−0.1 (10)	−0.4 (9)	0.0 (10)

	Form (I_5)	Form (I_6)	Form (I_7)	Form (I_8)
Crystal data
Pressure (GPa)	3.09	3.7	4.53	5
PTM	Petroleum ether	Petroleum ether	Petroleum ether	Petroleum ether
a, b, c (Å)	5.9951 (3), 8.7630 (5), 22.698 (3)	5.9640 (4), 8.7274 (6), 22.562 (4)	5.9177 (3), 8.6735 (5), 22.285 (4)	5.9146 (5), 8.6661 (8), 22.322 (5)
V (Å³)	1192.44 (19)	1174.4 (2)	1143.8 (2)	1144.2 (3)
μ (mm⁻¹)	0.12	0.12	0.12	0.12

Data collection
T_min, T_max	0.6602, 0.7449	0.654, 0.745	0.654, 0.745	0.659, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	5443, 739, 669	5226, 727, 643	5297, 575, 536	5001, 615, 549
R_int	0.044	0.045	0.040	0.050
θ_max (°)	23.3	23.2	23.2	23.2
(sin θ/λ)max (Å⁻¹)	0.555	0.555	0.553	0.554

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.070, 1.12	0.031, 0.070, 1.15	0.027, 0.064, 1.17	0.030, 0.071, 1.15
No. of reflections	739	727	575	615
Δρ_max, Δρ_min (e Å⁻³)	0.09, −0.15	0.11, −0.14	0.08, −0.11	0.09, −0.13
Absolute structure	Flack x determined using 245 quotients [(I⁺) − (I⁻)]/[(I⁺) + (I⁻)] (Parsons et al., 2013)	Flack x determined using 232 quotients [(I⁺) − (I⁻)]/[(I⁺) + (I⁻)] (Parsons et al., 2013)	Flack x determined using 202 quotients [(I⁺) − (I⁻)]/[(I⁺) + (I⁻)] (Parsons et al., 2013)	Flack x determined using 195 quotients [(I⁺) − (I⁻)]/[(I⁺) + (I⁻)] (Parsons et al., 2013)
Absolute structure parameter	0.0 (9)	−1.6 (10)	−0.5 (9)	−0.6 (10)

‡Computer programs: SAINT (Bruker, 2016

), SHELXT (Sheldrick, 2015b

), SHELXL (Sheldrick, 2015a

), Olex2 (Dolomanov et al., 2009

Table 2
For all structures: C₁₅H₂₂O₅, M_r = 282.32, triclinic, P1, Z = 4, crystal size (mm) 0.12 × 0.06 × 0.05. Experiments were carried out at 296 K with Mo Kα radiation using a Bruker D8 Venture diffractometer. Absorption was corrected for by multi-scan methods (SADABS; et al., 2015). Refinement was on 321 parameters with 95 restraints. H-atom parameters were constrained

	Form (II_1)	Form (II_2)	Form (II_3)	Form (II_4)
Crystal data
Pressure (GPa)	0.08	0.17	0.29	0.67
PTM	Silicone oil	Silicone oil	Silicone oil	Silicone oil
a, b, c (Å)	9.898 (2), 15.347 (4), 9.93 (5)	9.900 (2), 15.342 (4), 9.930 (5)	9.7831 (12), 15.150 (2), 9.832 (3)	9.637 (2), 14.741 (4), 9.796 (5)
α, β, γ (°)	86.79 (4), 102.83 (4), 89.075 (14)	86.75 (4), 102.56 (4), 89.144 (14)	86.565 (19), 103.35 (19), 89.287 (8)	88.93 (3), 103.73 (3), 89.846 (14)
V (Å³)	1468.8 (9)	1469.2 (9)	1414.5 (5)	1351.6 (9)
μ (mm⁻¹)	0.10	0.10	0.10	0.10

Data collection
T_min, T_max	0.634, 0.745	0.614, 0.745	0.635, 0.745	0.647, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	6845, 2686, 1019	7939, 2792, 1002	7362, 2713, 1129	5569, 2459, 1088
R_int	0.073	0.086	0.073	0.070
θ_max (°)	23.4	23.4	23.3	23.2
(sin θ/λ)max (Å⁻¹)	0.558	0.558	0.556	0.555

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.166, 0.96	0.068, 0.153, 0.98	0.062, 0.138, 0.97	0.075, 0.209, 0.98
No. of reflections	2686	2792	2713	2459
Δρ_max, Δρ_min (e Å⁻³)	0.10, −0.12	0.11, −0.11	0.11, −0.15	0.14, −0.17
Absolute structure	Flack x determined using 333 quotients [(I⁺) − (I⁻)]/[(I⁺) + (I⁻)] (Parsons et al., 2013)	Flack x determined using 333 quotients [(I⁺) − (I⁻)]/[(I⁺) + (I⁻)] (Parsons et al., 2013)	Flack x determined using 372 quotients [(I⁺) − (I⁻)]/[(I⁺) + (I⁻)] (Parsons et al., 2013)	Flack x determined using 344 quotients [(I⁺) − (I⁻)]/[(I⁺) + (I⁻)] (Parsons et al., 2013)
Absolute structure parameter	1.0 (10)	1.1 (10)	1.6 (10)	−0.5 (10)

	Form (II_5)	Form (II_6)
Crystal data
Pressure (GPa)	1.05	1.39
PTM	Silicone oil	Silicone oil
a, b, c (Å)	9.579 (3), 14.679 (5), 9.737 (7)	9.542 (5), 14.616 (8), 9.628 (12)
α, β, γ (°)	88.89 (5), 103.90 (4), 89.854 (18)	88.97 (8), 103.94 (8), 89.81 (3)
V (Å³)	1328.7 (11)	1303 (2)
μ (mm⁻¹)	0.11	0.11

Data collection
T_min, T_max	0.618, 0.745	0.549, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	3350, 1887, 888	2249, 1462, 590
R_int	0.059	0.069
θ_max (°)	23.3	23.2
(sin θ/λ)max (Å⁻¹)	0.555	0.555

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.080, 0.227, 1.03	0.108, 0.351, 1.05
No. of reflections	1887	1462
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.16	0.23, −0.24
Absolute structure	Flack x determined using 287 quotients [(I⁺) − (I⁻)]/[(I⁺) + (I⁻)] (Parsons et al., 2013)	Flack x determined using 169 quotients [(I⁺) − (I⁻)]/[(I⁺) + (I⁻)] (Parsons et al., 2013)
Absolute structure parameter	−1.0 (10)	−4.5 (10)

§Computer programs: SAINT (Bruker, 2016

), SHELXT (Sheldrick, 2015b

), SHELXL (Sheldrick, 2015a

), Olex2 (Dolomanov et al., 2009

2.6. Structural analysis

The equation of state (EoS) for the polymorphs was calculated using EoSFit (Angel et al., 2014 ). The unit-cell parameters from forms (I) and (III) were used to fit a third-order Birch–Murnaghan EoS (BMEoS). A second-order BMEoS was used for form (II) due to the limited number of data points.

ConQuest was used to search for and retrieve structures listed in the Cambridge Structural Database (CSD; Groom et al., 2016 ). The structures were visualized and analysed using Mercury (Macrae et al., 2020 ). The CellVol (Wilson et al., 2022 ) program was used to calculate the network and void volume of the systems as a function of pressure.

The PIXEL method was used to calculate intermolecular interaction energies of forms (I) and (III) facilitated by the MrPixel (Reeves et al., 2020 ) script through Mercury. Gaussian 09W (Frisch et al., 2009 ) was used to calculate the molecular electron density for input into PixelC (Gavezzotti, 2011 ; Gavezzotti, 2003 ). Both form (I) and form (III) possess Z′ ≤ 2, hence, the full PixelC calculation was performed to enable both the intermolecular interactions and the lattice energy to be calculated (Reeves et al., 2020).

3. Results and discussion

3.1. Form (I)

To provide an overall understanding of form (I) we will firstly give a brief description of the ambient crystal structure before describing the changes as a function of pressure. Form (I) is the most stable polymorph of ART and crystallizes in orthorhombic P2₁2₁2₁ with Z′ = 1. ART does not contain any hydrogen bond donors and so the crystal structure is composed of molecules interacting through weak CH⋯O and van der Waals interactions. The strongest interaction is between molecules stacked along the a direction involving a short contact between (C1—)H1⋯O3 [∼2.35 Å] and (C7—)H7⋯O4 [∼2.46 Å] [interaction 1; molecules of similar colour, −33.5 kJ mol⁻¹; Fig. 1(a)]. Neighbouring chains are then related by the 2₁-screw axis along the b direction (interaction 2; orange to light-green molecules or red to green molecules, −22.4 kJ mol⁻¹; Fig. 1). The final interaction then links the molecules in the two halves of the unit cell together (interaction 3; −15.8 kJ mol⁻¹; light-green to red molecules). The weaker interaction 3 results in a large portion of the void space being located in this region of the structure. Previous work has identified that void space and its compression can be a significant factor in the phase behaviour of a material (Turner et al., 2011 ; Wood et al., 2008 ; Wilson et al., 2022; Ostrowska et al., 2015 ).

Figure 1
(a) Strongest interactions in the ART structure looking down the b axis. Interaction 1 (between molecules of similar colour), interaction 2 (orange and light-green) and interaction 3 (light-green to red). (b) Interactions 1–3 between pairs of molecules in the crystal structure.

3.1.1. Effect of pressure on form (I)

ART was investigated under two different pressure regimes: pressures from ambient to 1200 bar (0.12 GPa); and pressures from 0 to 5 GPa. The lower pressure regime was conducted using the sapphire capillary cell on beamline I19 at Diamond Light Source (McMonagle et al., 2020).

ART compresses monotonically to 5 GPa without any change to the structure. The third-order BMEoS gives a bulk modulus (K₀) of 2.9 (10) GPa, V₀ = 1448.1 (10) Å³. As expected for a van der Waals solid, the material is relatively soft and its bulk modulus is lower compared with other van der Waals solids, e.g. naphthalene (K₀ = 7.9 GPa) (Likhacheva et al., 2014 ) or anthracene (K₀ = 6.08 GPa) (Oehzelt et al., 2002 ). Vaidya and Kennedy explored several other van der Waals compounds possessing bulk moduli exceeding that of ART, the lowest being biphenyl at K₀ = 4.5 GPa (Vaidya & Kennedy, 1971 ). All of these examples involve planar molecules where the compression is largely between the planes. On the other hand, ART is non-planar, giving rise to compression in all directions. This added flexibility likely contributes to the material's overall softness.

In response to hydrostatic pressure, the structure of ART indicates that the biggest reduction occurs in the b axis (Fig. 2). SCC data [Fig. 2(b)] show a clearer distinction between the compressibility of all three axes, with the b axis still being the most compressible. The a and c axes initially show a different compressibility to each other but converge to a similar rate above ∼2 GPa.

Figure 2
(a) Unit-cell volume fitted with third-order BMEoS as a function of pressure for form (I). (b) Compression behaviour of unit-cell parameters normalized using the ambient-pressure values in SCC. (c) Compression behaviour of unit-cell parameters from both SCC and DAC studies normalized using the ambient-pressure values in the DAC. Lines serve as a guide to the eye.

As the pressure increases, the overall lattice energy increases from −110.1 kJ mol⁻¹ to −69.3 kJ mol⁻¹ as a result of the steady relative increase in repulsion over attractive forces as molecules are pushed closer together. The internal molecular energy does not change substantially over the compression series (maximum 15 kJ mol⁻¹). This suggests that the molecular conformation remains stable due to its rather rigid molecular structure, and that compression occurs through changes in intermolecular packing. We have followed the compression of the structure through the analysis of the six most energetically favourable pairwise interactions (labelled 1–6; Fig. 3). These interactions are the major contributors to the stabilization of the crystal structure. Interactions 1–3 display much steeper curves compared to interactions 4–6. The increase in energy penalty is primarily driven by repulsion as the molecules are compressed together (interaction 1: 30.9 to 104.8 kJ mol⁻¹). Interaction 2 possesses a rather large centroid distance of ∼7.7 Å but still shows a steep increase in repulsion, which can be attributed to the orientation and proximity of a methyl group (C15) with respect to the oxygen atoms of the neighbouring molecule (O1 and O5). This leads to an increase in steric interactions and repulsion energy.

Figure 3
(a) Diagrams of the highest-energy interactions in the ART structure from PIXEL analysis. (b) Graph of the total interaction energy (in kJ mol⁻¹) against the distance between the molecular centroids of the molecules involved in the interaction (in Å). Lines serve as a guide to the eye.

The energies of interactions 4–6 are generally invariant on compression, suggesting that they are relatively soft. In particular, interactions 5 and 6 have a small energy penalty depicted by their flat curves in Fig. 3(b), and they can compress to a far greater extent than interaction 1. This behaviour can be rationalized by considering the distribution of void space within the crystal structure (Fig. 4). These voids, located around the central and lower regions of the unit cell, allow these molecules to move closer together and are visibly reduced at 5 GPa. These observations are commensurate with other studies that show that the location of the largest voids is often strongly correlated with the direction of greatest compressibility (Wood et al., 2008; Tomkowiak & Katrusiak, 2019 ; Ward et al., 2023 ).

Figure 4
(a) Void spaces (yellow) in the ART form (I) structure at ambient pressure with interactions 4 (blue), 5 (green) and 6 (black) from the central molecule (atom colour). Void spaces at ambient pressure consist of 213.03 Å³ and 15.6% of the total unit-cell volume. (b) Void spaces in the ART structure at 5 GPa with the void spacing making up 43.72 Å³ and 3.8% of the unit cell. with same molecular colour scheme. Void space analysis was set with a probe of 0.5 Å radius and 0.2 Å grid spacing for both ambient pressure and 5 GPa.

3.2. Form (II)

Chan et al. (1997) recrystallized ART from cyclohexane and identified the crystals as a new polymorph, form (II), which can be described by four molecules in the asymmetric unit. Form (II) manifests as thin, plate-like crystals, in contrast to form (I), which appears as thick rods. The density of form (II) is slightly lower than that of form (I), which is in line with the known stability and density rule of Burger & Ramberger (1979 ). Chan et al. (1997) highlighted the main difference between the polymorphs to be the different torsion angles, particularly around the ring systems where they can be up to 15° different. One of the key structural observations of form (II) is the relationship between the independent molecules. The molecules exhibit pseudo 2₁-screw axis along the b direction for the two sets of molecules [Fig. 5(a)] relating the red to the yellow molecule, and blue molecule to green molecule. The molecular packing lacks a formal symmetry relationship, due to slight variations in the spatial arrangement of the molecules.

Figure 5
(a) Molecular arrangement of ART form (II) at ambient conditions showing the unit-cell contents (Z = 4) coloured by symmetry equivalence. Blue circles highlight similar carbonyl groups on each of the molecules that help to indicate the pseudo-2₁ relationship between the molecules (red with yellow & blue with green). (b) The asymmetric unit coloured by element with exception of the carbonyl groups which are colour coded to link to Fig. 5

(a). The curved arrows represent the pseudo twofold rotation where the red molecule rotates and translates (dotted line) to the yellow molecule forming the pseudo 2₁-screw axis.

3.2.1. Effect of pressure on ART form (II)

One of the key challenges with the study of form (II) was that the crystals are very thin and fragile. Many of the crystals that we tested in the DAC did not diffract strongly enough for data collection, hence the data on form (II) was collated from two different studies: one in petroleum ether and the other in silicone oil (Fig. 6). The initial study using petroleum ether as the PTM was conducted using an annealed single crystal from cyclohexane. The annealing process was performed in a DAC without measurable pressure applied but enough to seal the system. Due to the low freezing pressure of cyclohexane (0.025 GPa) (Würflinger, 1975 ), the crystal was removed from the DAC and reloaded into another DAC for the compression study. Unfortunately, the initial compression of this crystal was to 1.95 GPa. At this pressure, the crystal has transformed to a new polymorph; however, we continued to study this phase to a maximum pressure of 5.4 GPa before decompression. There was no characterization of the crystal after the initial annealing to verify the starting polymorph; hence, we could not definitively assign this change to the compression process or whether annealing caused the change in polymorph. Therefore, a further study was required to identify the source of phase transition. Fortunately, a single crystal of sufficient quality was obtained from the ambient solution crystallizations without the requirement to anneal it. On this occasion, the crystal was loaded using silicone oil due to the scarcity of crystals of sufficient size and quality. Petroleum ether is highly volatile and, in our experience, leads to a higher proportion of failed loadings, i.e. where liquid is not present in cell or where the crystal is washed away from the diamond tip.

Figure 6
(a) Unit-cell dimensions of two different SC studies; blue shapes represent SC in silicone oil (crystal not annealed); orange shapes represent annealed SC compressed using petroleum ether as the PTM. (b) Molecular volume of ART for all studies. The blue triangles represent the study in silicone oil and the orange triangles represent the two studies in petroleum ether (filled: initial study; hollow: second study with unit cells only). Inset are pictures of the crystals used in the studies. The hole size of gasket is 250 µm for comparison of crystal size.

The data collected from a crystal in silicone oil [Fig. 6(b), blue triangles] indicate a smooth compression of the structure to ∼2 GPa. From ambient pressure to 2 GPa, the a and c axes compress to a similar extent reducing by 4.1%. Above 2 GPa, the b axis exhibits a sharp decrease indicating a single crystal to single crystal phase transition from form (II) to a new high-pressure polymorph that will be designated form (III), confirming our initial observation in petroleum ether.

From both the silicone oil and petroleum ether studies, we have been able to observe that the new phase has unit-cell parameters similar to form (II) but is now described as a monoclinic P2₁ structure (Table 3). The phase transition is characterized by a change from a Z′ = 4 structure to a Z′ = 2 structure through the increase in symmetry. The molecular volume of form (III) is 8.4% lower than form (II) indicating an increase in the density of the phase. Using void space analysis, form (II) exhibits a void space of 156.01 Å³, accounting for 12% of the unit-cell volume, whereas the new monoclinic phase shows a reduced void space of 128.40 Å³ or 10.1% of the unit cell. One of the unusual observations was at 2.02 GPa (indexing only), where there was a change in symmetry indicated by the indexing of a monoclinic unit cell, but not a significant change in molecular volume [Fig. 6(b); circled point]. This suggests that the change in symmetry and volume can be decoupled from one another in a two-stage process. Firstly, the molecules arrange themselves into the true P2₁ symmetry before the volume fully compresses. The volume reduction associated with the new form occurs later at 2.44 GPa.

Table 3
Experimental details

For all structures: C₁₅H₂₂O₅, M_r = 282.32, monoclinic, P2₁, Z = 4, crystal size (mm) 0.2 × 0.1 × 0.09. Experiments were carried out with Mo Kα radiation using a Bruker D8 Venture diffractometer. Absorption was corrected for by multi-scan methods (SADABS2016; Krause et al., 2015). Refinement was on 167 parameters with 47 restraints. H-atom parameters were constrained.

	Form (III_1)	Form (III_2)	Form (III_3)	Form (III_4)
Crystal data
Pressure (GPa)	1.95	3.25	3.71	5.05
PTM	Petroleum ether	Petroleum ether	Petroleum ether	Petroleum ether
Temperature (K)	295	296	296	296
a, b, c (Å)	9.344 (2), 14.133 (3), 9.554 (5)	9.186 (3), 13.927 (5), 9.469 (8)	9.1432 (14), 13.835 (2), 9.459 (4)	9.076 (2), 13.755 (4), 9.428 (7)
β (°)	104.73 (4)	104.43 (6)	104.69 (3)	104.60 (4)
V (Å³)	1220.2 (8)	1173.1 (12)	1157.5 (6)	1139.1 (9)
μ (mm⁻¹)	0.11	0.12	0.12	0.12

Data collection
T_min, T_max	0.491, 0.745	0.384, 0.745	0.649, 0.745	0.358, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	6348, 1335, 630	5153, 1256, 440	5284, 1210, 651	6090, 1265, 439
R_int	0.150	0.276	0.108	0.328
θ_max (°)	23.5	23.4	23.3	23.4
(sin θ/λ)max (Å⁻¹)	0.560	0.558	0.557	0.558

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.074, 0.252, 0.86	0.154, 0.441, 1.06	0.063, 0.123, 1.00	0.151, 0.286, 1.01
No. of reflections	1335	1256	1210	1265
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.23	0.52, −0.48	0.20, −0.17	0.24, −0.34
Absolute structure	Flack x determined using 213 quotients [(I⁺) − (I⁻)]/[(I⁺) + (I⁻)] (Parsons et al., 2013)	Flack x determined using 93 quotients [(I⁺)−(I⁻)]/[(I⁺) + (I⁻)] (Parsons et al., 2013)	Flack x determined using 222 quotients [(I⁺)−(I⁻)]/[(I⁺) + (I⁻)] (Parsons et al., 2013)	Flack x determined using 119 quotients [(I⁺) − (I⁻)]/[(I⁺) + (I⁻)] (Parsons et al., 2013)
Absolute structure parameter	0.5 (10)	−4.9 (10)	−0.3 (10)	−1.8 (10)

	Form (III_5)	Form (III_6)	Form (III_7)	Form (III_8)
Crystal data
Pressure (GPa)	5.44	4.52	3.88	2.57
PTM	Petroleum ether	Petroleum ether	Petroleum ether	Petroleum ether
Temperature (K)	296	296	296	296
a, b, c (Å)	9.0393 (13), 13.688 (2), 9.404 (4)	9.1279 (16), 13.819 (3), 9.461 (4)	9.1812 (15), 13.865 (3), 9.479 (4)	9.3601 (11), 14.1006 (18), 9.587 (3)
β (°)	104.79 (3)	104.86 (3)	104.89 (3)	104.87 (2)
V (Å³)	1125.0 (5)	1153.5 (6)	1166.2 (6)	1222.9 (5)
μ (mm⁻¹)	0.12	0.12	0.12	0.11

Data collection
T_min, T_max	0.580, 0.745	0.658, 0.745	0.392, 0.745	0.659, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	5919, 1239, 621	6247, 1259, 606	5516, 1332, 584	6478, 1324, 644
R_int	0.133	0.137	0.168	0.120
θ_max (°)	23.4	23.3	23.3	23.3
(sin θ/λ)max (Å⁻¹)	0.559	0.557	0.557	0.556

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.140, 0.98	0.062, 0.129, 0.99	0.092, 0.256, 0.97	0.066, 0.149, 0.98
No. of reflections	1239	1259	1332	1324
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.18	0.18, −0.20	0.25, −0.30	0.16, −0.15
Absolute structure	Flack x determined using 213 quotients [(I⁺) − (I⁻)]/[(I⁺) + (I⁻)] (Parsons et al., 2013)	Flack x determined using 206 quotients [(I⁺) − (I⁻)]/[(I⁺) + (I⁻)] (Parsons et al., 2013)	Flack x determined using 182 quotients [(I⁺) − (I⁻)]/[(I⁺) + (I⁻)] (Parsons et al., 2013)	Flack x determined using 213 quotients [(I⁺) − (I⁻)]/[(I⁺) + (I⁻)] (Parsons et al., 2013)
Absolute structure parameter	0.9 (10)	4.4 (10)	−1.1 (10)	−1.4 (10)

¶Computer programs: SAINT (Bruker, 2016

), SHELXT (Sheldrick, 2015b

), SHELXL (Sheldrick, 2015a

), Olex2 (Dolomanov et al., 2009

A further notable result from our examination of the two media was that the choice of PTM influences the pressure at which the phase transition occurs. For the petroleum ether study [orange triangles, Fig. 6(b)] multiple different crystals were used, and we discovered that the new phase can be obtained at pressure as low as 0.75 GPa using an indexed crystal (hollow orange triangles); these results are consistent across different crystals. To provide evidence as to the basis for this change, we observed that petroleum ether caused a visible shrinkage of the crystal indicating ART has some solubility in petroleum ether. This solubility may promote the transition to the new phase through solvent-mediated phase transition and nucleation on the surface of the mother crystal. This is not observed in silicone oil in which ART is insoluble, hence, the transition is delayed to higher pressure. It is not the first time PTM has been shown to impact the polymorphism of materials. Zakharov et al. (2016 ) demonstrated this in their study on β-chlorpropamide in various media (e.g. helium, paraffin). For example, when He was used as the PTM the phase transition from the orthorhombic β-polymorph to the new monoclinic phase, β^I_HP, appeared between 0.3 to 0.5 GPa. However, when using liquid paraffin as the PTM, unit-cell parameters similar to β^I_HP-chlorpropamide were observed at 0.1 GPa, and upon further compression to 0.3 GPa, a new triclinic phase, β^III_HP was formed.

3.3. Compression of form (III)

The new high-pressure phase possesses a monoclinic P2₁ structure with Z′ = 2. As mentioned previously, the molecules in form (II) are related by a pseudo-2₁ axis along the b axis. Over the phase transition, form (III) adopts a true 2₁ screw axis formalizing the relationship between the molecules. This leads to a reduction in the length of the b axis allowing for denser and more efficient molecular packing. A comparison the structures of forms (II) and (III) indicates a packing similarity of 15/15 molecules and a root-mean-square similarity score of 0.305 indicating a strong similarity which explains how the single crystal is maintained over the transition (Fig. 7). A comparison of the unit-cell parameters for forms (I), (II), and (III) at closer pressure points is found in Table 4.

Table 4
Structural parameters of ART polymorphs at closest pressure points

Form	Form (I)	Form (II)	Form (III)
Pressure (GPa)	0.30 (5)†	0.29 (5)	0.75 (5)
a (Å)	6.2555 (4)	9.7831 (12)	9.523 (5)
b (Å)	9.1513 (6)	15.150 (2)	14.360 (8)
c (Å)	23.860 (4)	9.832 (3)	9.697 (15)
α (°)	90	86.565 (19)	90
β (°)	90	103.385 (19)	103.30 (9)
γ (°)	90	89.287 (8)	90
V (Å³)	1365.9 (3)	1414.5 (5)	1290 (2)
Space group	P2₁2₁2₁	P1	P2₁
Z	4	4	4
Z′	1	4	2

†Standard uncertainty of ±0.05 GPa (Chervin et al., 2001

Figure 7
Overlay of the triclinic and high-pressure monoclinic forms of ART. The darker-coloured molecules represent the triclinic form at 1.39 GPa [highest form (II) data pressure], while the pastel-coloured molecules represent the high-pressure monoclinic form at 1.95 GPa. The root-mean-square deviation is 0.305 with 15/15 molecules overlapping indicating a strong similarity. The β angle remains consistent between the phases with the alpha and gamma becoming 90°. This is achieved through the chains sliding with respect to each other along the b direction.

Pixel analysis of form (III) has been performed on three pressure points from 1.95 GPa onwards. The molecules in interactions 1, 4 and 5 are related by a 2₁ screw axis and these contacts extend along the b axis [Fig. 8(a)]. Interaction 3 (blue) and interaction 4 (purple) are the most stabilizing as the total energies reach approximately −30 kJ mol⁻¹ at centroid distances near 6.0 Å. Interaction 3 displays a much steeper curve as the repulsive component increases significantly from 55.1 to 110.7 kJ mol⁻¹ with pressure. A comparison of the interactions over a similar pressure range in form (III) [Fig. 8(b), square data points] and form (I) [Fig. 8(b), triangle data points] provides a clearer insight into how their packing responds differently under compression [Fig. 8(b)]. The response of the two forms to pressure is similar with all interactions showing an increase in energy due to the increase in repulsive forces. Form (III) shows a more dispersed set of interactions over the computed range, specifically, interactions 2 and 6 occurring at longer centroid distances compared with form (I). The longer interactions of form (I) (interactions 4 to 6) are more face-to-face interactions of the ring systems as opposed to the edge-to-edge interactions in form (III) (interactions 2 and 6).

Figure 8
(a) Structures of the highest-energy interactions in the ART structure from PIXEL analysis. Molecules in grey represent the central molecule and the coloured molecule represents the transformed molecules. The curved arrows represent the pseudo-twofold rotation, and the dotted arrows highlight the translation in the pseudo 2₁-screw axis. (b) Graph of the total interaction energy (in kJ mol⁻¹) against the distance between the molecular centroids of the molecules involved in the interaction (in Å) for form (III) shown as square symbols. Triangles represent form (I) interactions over a similar pressure range. Lines serve as a guide to the eye.

3.4. Comparison of polymorphic forms of ART

The mechanical responses of the three polymorphic forms of ART were fitted to the BMEoS, revealing distinct differences in compressibility.Form (I), fitted with a third-order BMEoS, exhibits a low bulk modulus K₀ of 2.9 (10) GPa and V₀ = 1448.1 (10) Å³, indicating its relatively soft and compressible nature. Due to the paucity of data, form (II) was fit using a second-order BMEoS with a bulk modulus [K₀] of 7.7 (11) GPa and V₀ = 1480 (16) Å³. Form (III) is stiffer, with a bulk modulus of 12 (4) GPa and V₀ = 1357 (18) Å³ also determined using a third-order BMEoS. The smaller V₀ of form (III) points to a denser packing arrangement, consistent with its higher bulk modulus. The higher uncertainties are a due to a paucity of data at low pressures given the narrow stability range of form (III).

The data shown in Fig. 9 represent molecular volume data from multiple experiments on different crystals of each form highlighted by polymorph. Data for form (II) were only collected to 1.39 GPa due to the phase transition and shows slightly higher molecular volumes than forms (I) and (III). Notably, the silicone oil studies (open blue squares) of form (II) show slightly higher molecular volume at similar pressures compared to petroleum ether studies [closed blue squares; Fig. 9(b)] suggesting a better transmission of pressure to the sample with this media over silicone oil. At higher pressures, forms (I) and (III) converge to a similar molecular volume at ∼5 GPa with a subtle difference in molecular volume at 5.4 GPa.

Figure 9
Unit-cell volume fitted with third-order BMEoS for forms (I) and (III), and second-order BMEoS for form (II). (b) Molecular volume versus pressure summary of all studies with different crystals or different PTM. Form (I) is represented by red squares; form (II) is in blue squares and form (III) is in black squares; closed squares represent petroleum (pet) ether studies; open squares are silicone (sil) oil studies.

Void spaces in crystal structures provide an opportunity to rationalize the behaviour of organic materials under pressure. Wilson et al. (2022) have proposed a method by which the volume of the crystal structure can be separated into two components: (i) the network volume including space occupied by atoms and their intermolecular contacts (based on van der Waals radii) and (ii) the void volume based on unoccupied space. This method addresses the issue of access to enclosed void spaces when the rolling ball method is employed. Using this method, we have analysed the changes in both the network and void volumes as a function of pressure (Fig. 10). Form (I) compresses smoothly across both the network and void volumes to 5 GPa without any distinct changes to the mechanism of compression. However, the compression of form (II) shows discontinuities in both the network and void volumes over the phase transition.

Figure 10
CellVol (Wilson et al., 2022

) analysis for ART (a) form (I) network volume against pressure (GPa) in red. (b) Void volume of form (I) against pressure. (c) Form (II) in silicone oil (blue) and form (III) in petroleum ether (black) network volume against pressure. (d) Form in silicone oil (blue) and form (III) in petroleum ether (black) void volume against pressure. The form (II) to form (III) phase transition is observed between 1.5 and 2.02 GPa in silicone oil. Lines serve as a guide to the eye.

One of the key and unusual observations for form (II), from the molecular volume and symmetry perspective, was at 2.02 GPa where the structure seemed to change symmetry, yet the molecular volume remained consistent before reducing in the next data point. By deconvoluting the compression into network and void volumes we are able to see how the compression changes over this pressure range and provide further detail to enhance our understanding of the behaviour which we believe is a two-step process. Prior to the phase transition (between 1.05 and 1.39 GPa), the network volume shows a drop in volume which was coined by Wilson et al. (2022) as `premonitory behaviour' in their explanation for the behaviour in 3-fluorosalicylaldoxime. In their work, the authors used a Vinet third-order EoS to fit the network volume of 3-fluorosalicylaldoxime. They observed that the last two data points, at 5.8 and 6.5 GPa, fell below the fitted curve prior to a reconstructive transition, above which no further data could be collected. We see this effect in the compression of form (II). The drop in network volume means that while the volume occupied by the atoms and their intermolecular contacts has reduced; no discontinuity is observed in the void volume at this point. This signifies that in this first stage the molecules are starting to pre-arrange into a more efficiently packed arrangement. If we take the `chains' of molecules described in Fig. 5, i.e. red/yellow and blue/green pairs, we hypothesize that the molecules subtly reorganize so that they establish a relationship approximating a 2₁-screw axis within each individual pair reducing the network volume prior to the transition. At the next pressure point, the symmetry is formalized with the chains sliding across each other (along the b direction) resulting in a structure that can be described in a monoclinic crystal system. The second stage is the increase in packing efficiency where the two chains compress together to reduce the void volume (29% reduction).

Our investigation of the behaviour of ART polymorphs at high pressures shows clear variations in their phase stability and compressibility under different conditions. From an energetic perspective, the overall lattice energies of form (I) and form (III) indicate that they are close in energy at ∼1.9 GPa. Unfortunately, the high Z′ precludes the calculation of the lattice energy of form (II). Arguably, the rate of change of the lattice energy for form (III) is higher than for form (I) and we observe this in the overall repulsion energies where form (III) is 11.9 kJ mol⁻¹ more repulsive over the same range [Fig. 11; repulsion energies form (I): 226.6 to 387.5 kJ mol⁻¹; form (III) (from 1.9 GPa) 256.3 to 429.1 kJ mol⁻¹].

Figure 11
Lattice energy of form (I) (red squares) and form (III) (black squares) as a function of pressure.

4. Conclusion

In conclusion, the high-pressure behaviour of the three ART polymorphs reveals distinct structural responses to compression. Form (I) is the most compressible, suggesting a greater ability to react to external pressure. In contrast, form (II) undergoes a phase transition to a new high-pressure phase, form (III). Interestingly the transition is observed at 0.75 GPa in petroleum ether but delayed to 2.02 GPa in silicone oil, underscoring the importance of experimental conditions in polymorph stability and that the solubility in the PTM, however slight, can influence outcome. Form (III) is structurally related to form (II), where the molecules move from a pseudo-2₁ screw axis in form (II) to a formal monoclinic P2₁ structure, reducing the asymmetric unit from Z′ = 4 to Z′ = 2. Analysis of the transition shows that molecules pre-set themselves into a more efficient packing arrangement before the formal crystallographic symmetry is observed. This is a further observation that whilst the solid may exhibit the same solid-state structure, the molecular positions may yield information about how the molecules interact prior to any formal change in symmetry. This is particularly relevant in Z′ > 1 structures, where molecules can move independently from each other due to the lack of symmetry constraints.

Supporting information

CCDC references: 2465849; 2465850; 2465851; 2465852; 2465853; 2465854; 2465855; 2465856

Link https://doi.org/10.15129/2af1df8c-307a-4478-bd47-82e5e5c32a4b
Access to data once paper has been accepted and all data are added to the link

Crystal structure: contains datablocks FormI_1, FormI_2, FormI_3, FormI_4, FormI_5, FormI_6, FormI_7, FormI_8, FormII_1, FormII_2, FormII_3, FormII_4, FormII_5, FormII_6, FormIII_1, FormIII_2, FormIII_3, FormIII_4, FormIII_5, FormIII_6, FormIII_7, FormIII_8. DOI: https://doi.org/10.1107/S205252062600291X/aw5104sup1.cif

Structure factors: contains datablock FormII_1. DOI: https://doi.org/10.1107/S205252062600291X/aw5104FormII_1sup2.hkl

Structure factors: contains datablock FormII_2. DOI: https://doi.org/10.1107/S205252062600291X/aw5104FormII_2sup3.hkl

Structure factors: contains datablock FormII_3. DOI: https://doi.org/10.1107/S205252062600291X/aw5104FormII_3sup4.hkl

Structure factors: contains datablock FormII_4. DOI: https://doi.org/10.1107/S205252062600291X/aw5104FormII_4sup5.hkl

Structure factors: contains datablock FormII_5. DOI: https://doi.org/10.1107/S205252062600291X/aw5104FormII_5sup6.hkl

Structure factors: contains datablock FormII_6. DOI: https://doi.org/10.1107/S205252062600291X/aw5104FormII_6sup7.hkl

Structure factors: contains datablock FormIII_1. DOI: https://doi.org/10.1107/S205252062600291X/aw5104FormIII_1sup8.hkl

Structure factors: contains datablock FormIII_2. DOI: https://doi.org/10.1107/S205252062600291X/aw5104FormIII_2sup9.hkl

Structure factors: contains datablock FormIII_3. DOI: https://doi.org/10.1107/S205252062600291X/aw5104FormIII_3sup10.hkl

Structure factors: contains datablock FormIII_4. DOI: https://doi.org/10.1107/S205252062600291X/aw5104FormIII_4sup11.hkl

Structure factors: contains datablock FormIII_5. DOI: https://doi.org/10.1107/S205252062600291X/aw5104FormIII_5sup12.hkl

Structure factors: contains datablock FormIII_6. DOI: https://doi.org/10.1107/S205252062600291X/aw5104FormIII_6sup13.hkl

Structure factors: contains datablock FormIII_7. DOI: https://doi.org/10.1107/S205252062600291X/aw5104FormIII_7sup14.hkl

Structure factors: contains datablock FormIII_8. DOI: https://doi.org/10.1107/S205252062600291X/aw5104FormIII_8sup15.hkl

Structure factors: contains datablock FormI_3. DOI: https://doi.org/10.1107/S205252062600291X/aw5104FormI_3sup16.hkl

Structure factors: contains datablock FormI_4. DOI: https://doi.org/10.1107/S205252062600291X/aw5104FormI_4sup17.hkl

Structure factors: contains datablock FormI_5. DOI: https://doi.org/10.1107/S205252062600291X/aw5104FormI_5sup18.hkl

Structure factors: contains datablock FormI_6. DOI: https://doi.org/10.1107/S205252062600291X/aw5104FormI_6sup19.hkl

Structure factors: contains datablock FormI_7. DOI: https://doi.org/10.1107/S205252062600291X/aw5104FormI_7sup20.hkl

Structure factors: contains datablock FormI_8. DOI: https://doi.org/10.1107/S205252062600291X/aw5104FormI_8sup21.hkl

Structure factors: contains datablock mo_artemisinin001_0m. DOI: https://doi.org/10.1107/S205252062600291X/aw5104FormI_1sup22.hkl

Structure factors: contains datablock artemisinin003. DOI: https://doi.org/10.1107/S205252062600291X/aw5104FormI_2sup23.hkl

Includes Figs S1-S5 and Tables S1 and S2. DOI: https://doi.org/10.1107/S205252062600291X/aw5104sup24.pdf

Computing details top

Artemesinin (FormI_1) top

Crystal data top

C₁₅H₂₂O₅	D_x = 1.373 Mg m⁻³
M_r = 282.32	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 1844 reflections
a = 6.2555 (4) Å	θ = 2.4–20.9°
b = 9.1513 (6) Å	µ = 0.10 mm⁻¹
c = 23.860 (4) Å	T = 296 K
V = 1365.9 (3) Å³	Needle, clear colourless
Z = 4	0.25 × 0.18 × 0.09 mm
F(000) = 608

Data collection top

Bruker APEX-II CCD diffractometer	658 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.047
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0882 before and 0.0507 after correction. The Ratio of minimum to maximum transmission is 0.8956. The λ/2 correction factor is Not present.	θ_max = 23.3°, θ_min = 2.4°
T_min = 0.667, T_max = 0.745	h = −6→6
5881 measured reflections	k = −10→10
748 independent reflections	l = −8→8

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.044	w = 1/[σ²(F_o²) + (0.0639P)² + 1.1013P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.122	(Δ/σ)_max < 0.001
S = 1.12	Δρ_max = 0.14 e Å⁻³
748 reflections	Δρ_min = −0.14 e Å⁻³
184 parameters	Absolute structure: Flack x determined using 237 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
206 restraints	Absolute structure parameter: 0.5 (8)
Primary atom site location: dual

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.

Refinement. RIGU restraint was applied

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

	x	y	z	U_iso*/U_eq
O1	0.2018 (9)	0.5627 (5)	0.7323 (7)	0.056 (5)
O2	0.3941 (10)	0.5674 (6)	0.6954 (8)	0.056 (5)
O3	0.0276 (10)	0.3838 (7)	0.6818 (7)	0.056 (5)
O4	−0.0060 (9)	0.5784 (6)	0.6230 (7)	0.065 (7)
O5	−0.0611 (10)	0.7919 (7)	0.5867 (8)	0.069 (9)
C1	0.4930 (14)	0.3452 (9)	0.6481 (9)	0.055 (5)
H1	0.635157	0.373900	0.661346	0.066*
C2	0.4023 (15)	0.2409 (10)	0.6913 (9)	0.062 (6)
H2A	0.514392	0.172993	0.701871	0.074*
H2B	0.289825	0.184430	0.673567	0.074*
C3	0.3098 (15)	0.3094 (10)	0.7459 (10)	0.064 (6)
H3A	0.258729	0.231530	0.769953	0.077*
H3B	0.423912	0.359600	0.765528	0.077*
C4	0.1272 (17)	0.4171 (9)	0.7358 (10)	0.058 (6)
C5	0.1244 (14)	0.4504 (9)	0.6354 (10)	0.050 (6)
H5	0.114077	0.383107	0.603515	0.059*
C6	0.3585 (12)	0.4866 (10)	0.6444 (10)	0.051 (5)
C7	0.4382 (14)	0.5854 (10)	0.5968 (10)	0.056 (5)
H7	0.587001	0.610650	0.605216	0.067*
C8	0.4372 (15)	0.5061 (10)	0.5407 (10)	0.063 (6)
H8A	0.487497	0.570745	0.511350	0.076*
H8B	0.293181	0.474994	0.531504	0.076*
C9	0.5849 (14)	0.3730 (10)	0.5456 (10)	0.065 (6)
H9A	0.583544	0.320785	0.510246	0.078*
H9B	0.729736	0.406995	0.551994	0.078*
C10	0.5253 (16)	0.2679 (10)	0.5919 (9)	0.059 (5)
H10	0.388718	0.222839	0.581579	0.070*
C11	0.3071 (13)	0.7278 (9)	0.5999 (10)	0.064 (7)
H11	0.343057	0.775404	0.635445	0.077*
C12	0.0697 (14)	0.7032 (10)	0.5998 (11)	0.056 (9)
C13	0.3663 (15)	0.8348 (9)	0.5527 (11)	0.078 (9)
H13A	0.518362	0.848721	0.552179	0.116*
H13B	0.296982	0.926897	0.559193	0.116*
H13C	0.320410	0.795697	0.517396	0.116*
C14	0.6914 (19)	0.1438 (11)	0.5979 (11)	0.074 (9)
H14A	0.817905	0.181214	0.615640	0.110*
H14B	0.727191	0.106572	0.561495	0.110*
H14C	0.632393	0.066699	0.620362	0.110*
C15	−0.0457 (17)	0.4187 (11)	0.7789 (12)	0.073 (7)
H15A	0.016662	0.429461	0.815483	0.110*
H15B	−0.124198	0.328677	0.777288	0.110*
H15C	−0.140600	0.499023	0.771835	0.110*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.046 (3)	0.035 (3)	0.087 (17)	−0.001 (2)	0.014 (6)	0.007 (5)
O2	0.036 (3)	0.041 (3)	0.091 (15)	−0.007 (3)	0.004 (5)	0.000 (5)
O3	0.033 (3)	0.043 (3)	0.091 (15)	−0.006 (3)	0.002 (5)	0.011 (5)
O4	0.028 (3)	0.050 (3)	0.12 (2)	0.001 (2)	0.001 (5)	0.013 (6)
O5	0.051 (4)	0.056 (4)	0.10 (3)	0.014 (3)	−0.005 (6)	0.011 (7)
C1	0.031 (4)	0.038 (4)	0.097 (16)	0.002 (3)	−0.001 (6)	−0.003 (6)
C2	0.046 (5)	0.041 (4)	0.099 (17)	0.010 (4)	−0.003 (8)	0.005 (7)
C3	0.052 (5)	0.046 (5)	0.095 (18)	0.004 (4)	−0.004 (8)	0.000 (7)
C4	0.048 (5)	0.035 (4)	0.092 (17)	−0.004 (4)	0.008 (7)	0.006 (6)
C5	0.034 (4)	0.033 (4)	0.082 (17)	0.000 (3)	0.007 (6)	−0.003 (6)
C6	0.025 (4)	0.036 (4)	0.094 (14)	−0.002 (3)	0.004 (5)	−0.004 (6)
C7	0.030 (4)	0.039 (4)	0.098 (16)	−0.008 (4)	−0.004 (7)	0.005 (6)
C8	0.042 (5)	0.045 (4)	0.102 (18)	−0.005 (4)	−0.005 (8)	0.003 (7)
C9	0.046 (4)	0.046 (4)	0.104 (19)	−0.001 (4)	0.002 (8)	0.006 (7)
C10	0.041 (5)	0.036 (4)	0.098 (16)	−0.001 (4)	−0.003 (7)	−0.004 (6)
C11	0.040 (4)	0.037 (4)	0.12 (2)	−0.005 (3)	−0.006 (7)	0.010 (7)
C12	0.041 (4)	0.046 (4)	0.08 (3)	0.003 (4)	−0.009 (7)	0.000 (8)
C13	0.051 (5)	0.044 (5)	0.14 (3)	0.000 (4)	−0.001 (10)	0.033 (9)
C14	0.057 (6)	0.050 (5)	0.11 (3)	0.011 (4)	−0.008 (9)	−0.007 (8)
C15	0.062 (5)	0.049 (5)	0.11 (2)	0.001 (5)	0.021 (9)	0.009 (9)

Geometric parameters (Å, º) top

O1—O2	1.492 (14)	C7—C8	1.52 (2)
O1—C4	1.414 (10)	C7—C11	1.541 (12)
O2—C6	1.44 (2)	C8—H8A	0.9700
O3—C4	1.46 (2)	C8—H8B	0.9700
O3—C5	1.40 (2)	C8—C9	1.533 (12)
O4—C5	1.458 (11)	C9—H9A	0.9700
O4—C12	1.355 (13)	C9—H9B	0.9700
O5—C12	1.194 (11)	C9—C10	1.51 (2)
C1—H1	0.9800	C10—H10	0.9800
C1—C2	1.52 (2)	C10—C14	1.546 (13)
C1—C6	1.546 (12)	C11—H11	0.9800
C1—C10	1.53 (3)	C11—C12	1.502 (12)
C2—H2A	0.9700	C11—C13	1.54 (2)
C2—H2B	0.9700	C13—H13A	0.9600
C2—C3	1.56 (2)	C13—H13B	0.9600
C3—H3A	0.9700	C13—H13C	0.9600
C3—H3B	0.9700	C14—H14A	0.9600
C3—C4	1.527 (13)	C14—H14B	0.9600
C4—C15	1.494 (17)	C14—H14C	0.9600
C5—H5	0.9800	C15—H15A	0.9600
C5—C6	1.517 (13)	C15—H15B	0.9600
C6—C7	1.53 (2)	C15—H15C	0.9600
C7—H7	0.9800

C4—O1—O2	109.1 (9)	C7—C8—H8A	110.1
C6—O2—O1	111.1 (8)	C7—C8—H8B	110.1
C5—O3—C4	114.9 (9)	C7—C8—C9	108.0 (15)
C12—O4—C5	124.4 (7)	H8A—C8—H8B	108.4
C2—C1—H1	106.7	C9—C8—H8A	110.1
C2—C1—C6	111.2 (12)	C9—C8—H8B	110.1
C2—C1—C10	110.8 (10)	C8—C9—H9A	108.7
C6—C1—H1	106.7	C8—C9—H9B	108.7
C10—C1—H1	106.7	H9A—C9—H9B	107.6
C10—C1—C6	114.2 (16)	C10—C9—C8	114.3 (13)
C1—C2—H2A	108.0	C10—C9—H9A	108.7
C1—C2—H2B	108.0	C10—C9—H9B	108.7
C1—C2—C3	117.0 (9)	C1—C10—H10	107.4
H2A—C2—H2B	107.3	C1—C10—C14	110.3 (16)
C3—C2—H2A	108.0	C9—C10—C1	112.3 (10)
C3—C2—H2B	108.0	C9—C10—H10	107.4
C2—C3—H3A	108.8	C9—C10—C14	111.7 (13)
C2—C3—H3B	108.8	C14—C10—H10	107.4
H3A—C3—H3B	107.7	C7—C11—H11	107.2
C4—C3—C2	114.0 (16)	C12—C11—C7	113.5 (8)
C4—C3—H3A	108.8	C12—C11—H11	107.2
C4—C3—H3B	108.8	C12—C11—C13	109.4 (12)
O1—C4—O3	106.6 (14)	C13—C11—C7	112.1 (13)
O1—C4—C3	111.7 (8)	C13—C11—H11	107.2
O1—C4—C15	105.6 (11)	O4—C12—C11	118.1 (10)
O3—C4—C3	108.9 (13)	O5—C12—O4	116.1 (8)
O3—C4—C15	107.5 (11)	O5—C12—C11	125.2 (9)
C15—C4—C3	116.0 (14)	C11—C13—H13A	109.5
O3—C5—O4	105.5 (10)	C11—C13—H13B	109.5
O3—C5—H5	108.1	C11—C13—H13C	109.5
O3—C5—C6	113.6 (16)	H13A—C13—H13B	109.5
O4—C5—H5	108.1	H13A—C13—H13C	109.5
O4—C5—C6	113.2 (7)	H13B—C13—H13C	109.5
C6—C5—H5	108.1	C10—C14—H14A	109.5
O2—C6—C1	107.3 (14)	C10—C14—H14B	109.5
O2—C6—C5	112.4 (13)	C10—C14—H14C	109.5
O2—C6—C7	105.8 (9)	H14A—C14—H14B	109.5
C5—C6—C1	110.5 (8)	H14A—C14—H14C	109.5
C5—C6—C7	109.7 (14)	H14B—C14—H14C	109.5
C7—C6—C1	111.0 (12)	C4—C15—H15A	109.5
C6—C7—H7	107.2	C4—C15—H15B	109.5
C6—C7—C11	106.9 (12)	C4—C15—H15C	109.5
C8—C7—C6	111.6 (10)	H15A—C15—H15B	109.5
C8—C7—H7	107.2	H15A—C15—H15C	109.5
C8—C7—C11	116.3 (15)	H15B—C15—H15C	109.5
C11—C7—H7	107.2

O1—O2—C6—C1	−107.9 (10)	C5—O3—C4—C3	−86.4 (10)
O1—O2—C6—C5	13.7 (14)	C5—O3—C4—C15	147.2 (8)
O1—O2—C6—C7	133.5 (7)	C5—O4—C12—O5	172.2 (19)
O2—O1—C4—O3	−73.1 (11)	C5—O4—C12—C11	−16 (3)
O2—O1—C4—C3	46 (2)	C5—C6—C7—C8	−65.9 (13)
O2—O1—C4—C15	172.8 (12)	C5—C6—C7—C11	62.2 (15)
O2—C6—C7—C8	172.6 (8)	C6—C1—C2—C3	−37.7 (17)
O2—C6—C7—C11	−59.3 (12)	C6—C1—C10—C9	45.2 (12)
O3—C5—C6—O2	−51.3 (13)	C6—C1—C10—C14	170.4 (8)
O3—C5—C6—C1	69 (2)	C6—C7—C8—C9	−60.0 (10)
O3—C5—C6—C7	−168.7 (10)	C6—C7—C11—C12	−53 (2)
O4—C5—C6—O2	69 (2)	C6—C7—C11—C13	−177.9 (12)
O4—C5—C6—C1	−171.2 (17)	C7—C8—C9—C10	57.5 (14)
O4—C5—C6—C7	−48 (2)	C7—C11—C12—O4	31 (3)
C1—C2—C3—C4	59.1 (12)	C7—C11—C12—O5	−158 (2)
C1—C6—C7—C8	56.5 (13)	C8—C7—C11—C12	72 (2)
C1—C6—C7—C11	−175.4 (13)	C8—C7—C11—C13	−52.6 (14)
C2—C1—C6—O2	70.2 (13)	C8—C9—C10—C1	−50.5 (15)
C2—C1—C6—C5	−53 (2)	C8—C9—C10—C14	−175.0 (14)
C2—C1—C6—C7	−174.7 (12)	C10—C1—C2—C3	−165.8 (10)
C2—C1—C10—C9	171.7 (8)	C10—C1—C6—O2	−163.6 (9)
C2—C1—C10—C14	−63.0 (11)	C10—C1—C6—C5	73.6 (19)
C2—C3—C4—O1	−94.0 (17)	C10—C1—C6—C7	−48.4 (14)
C2—C3—C4—O3	23.5 (12)	C11—C7—C8—C9	177.1 (8)
C2—C3—C4—C15	144.9 (12)	C12—O4—C5—O3	150.1 (17)
C4—O1—O2—C6	46.9 (15)	C12—O4—C5—C6	25 (3)
C4—O3—C5—O4	−99.0 (11)	C13—C11—C12—O4	156.7 (16)
C4—O3—C5—C6	25.5 (12)	C13—C11—C12—O5	−32 (3)
C5—O3—C4—O1	34.3 (11)

(FormI_2) top

Crystal data top

C₁₅H₂₂O₅	D_x = 1.474 Mg m⁻³
M_r = 282.32	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 1730 reflections
a = 6.1207 (4) Å	θ = 2.4–22.1°
b = 8.9193 (6) Å	µ = 0.11 mm⁻¹
c = 23.311 (4) Å	T = 296 K
V = 1272.6 (2) Å³	Needle, colourless
Z = 4	0.25 × 0.18 × 0.09 mm
F(000) = 608

Data collection top

Bruker APEX-II CCD diffractometer	665 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.045
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0803 before and 0.0539 after correction. The Ratio of minimum to maximum transmission is 0.8577. The λ/2 correction factor is Not present.	θ_max = 23.3°, θ_min = 2.4°
T_min = 0.639, T_max = 0.745	h = −6→6
5140 measured reflections	k = −9→9
779 independent reflections	l = −10→9

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) + (0.067P)² + 5.0439P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.182	(Δ/σ)_max < 0.001
S = 1.16	Δρ_max = 0.41 e Å⁻³
779 reflections	Δρ_min = −0.36 e Å⁻³
184 parameters	Absolute structure: Flack x determined using 234 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
206 restraints	Absolute structure parameter: −0.1 (10)

Special details top

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

	x	y	z	U_iso*/U_eq
O1	0.1932 (14)	0.5655 (8)	0.7312 (9)	0.048 (6)
O2	0.3919 (15)	0.5679 (10)	0.6963 (10)	0.049 (5)
O3	0.0174 (15)	0.3793 (10)	0.6819 (9)	0.047 (5)
O4	−0.0133 (13)	0.5798 (9)	0.6203 (10)	0.044 (8)
O5	−0.0668 (16)	0.8024 (10)	0.5871 (11)	0.050 (10)
C1	0.496 (2)	0.3415 (14)	0.6495 (12)	0.047 (5)
H1	0.640128	0.372111	0.663224	0.056*
C2	0.400 (2)	0.2346 (14)	0.6938 (11)	0.043 (6)
H2A	0.287597	0.175486	0.675091	0.051*
H2B	0.514494	0.165978	0.705488	0.051*
C3	0.301 (2)	0.3026 (15)	0.7477 (12)	0.048 (6)
H3A	0.244090	0.222778	0.771682	0.058*
H3B	0.415153	0.353378	0.769153	0.058*
C4	0.119 (2)	0.4131 (13)	0.7350 (12)	0.047 (6)
C5	0.118 (2)	0.4476 (15)	0.6349 (13)	0.045 (6)
H5	0.107536	0.377786	0.602542	0.054*
C6	0.3568 (19)	0.4852 (14)	0.6423 (11)	0.041 (5)
C7	0.441 (2)	0.5854 (14)	0.5951 (11)	0.041 (5)
H7	0.592396	0.610936	0.604222	0.050*
C8	0.442 (2)	0.5006 (15)	0.5387 (13)	0.048 (6)
H8A	0.494920	0.565286	0.508263	0.057*
H8B	0.294454	0.469489	0.529064	0.057*
C9	0.589 (2)	0.3638 (15)	0.5439 (14)	0.061 (6)
H9A	0.738147	0.397146	0.549055	0.073*
H9B	0.581880	0.307514	0.508387	0.073*
C10	0.528 (2)	0.2595 (14)	0.5937 (12)	0.049 (6)
H10	0.389068	0.211084	0.583877	0.058*
C11	0.308 (2)	0.7332 (13)	0.5949 (13)	0.041 (7)
H11	0.349977	0.784686	0.630371	0.050*
C12	0.068 (2)	0.7087 (14)	0.6003 (15)	0.042 (10)
C13	0.369 (2)	0.8395 (16)	0.5475 (14)	0.059 (9)
H13A	0.525407	0.841581	0.543512	0.088*
H13B	0.317412	0.938265	0.556609	0.088*
H13C	0.304538	0.806545	0.512212	0.088*
C14	0.704 (3)	0.1358 (15)	0.5971 (18)	0.070 (10)
H14A	0.841074	0.179574	0.608025	0.104*
H14B	0.718844	0.088686	0.560241	0.104*
H14C	0.661518	0.062356	0.625006	0.104*
C15	−0.063 (2)	0.4177 (16)	0.7776 (14)	0.057 (7)
H15A	−0.004799	0.436274	0.815161	0.085*
H15B	−0.138534	0.323346	0.777444	0.085*
H15C	−0.162965	0.496376	0.767527	0.085*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.032 (4)	0.023 (4)	0.090 (17)	−0.003 (4)	0.009 (8)	0.004 (6)
O2	0.032 (4)	0.026 (5)	0.090 (15)	−0.006 (4)	−0.002 (7)	−0.007 (6)
O3	0.028 (5)	0.028 (5)	0.085 (16)	−0.001 (4)	0.002 (6)	0.002 (6)
O4	0.025 (4)	0.033 (4)	0.07 (2)	0.005 (3)	0.007 (7)	0.018 (7)
O5	0.043 (5)	0.037 (5)	0.07 (3)	0.011 (4)	−0.003 (8)	0.014 (8)
C1	0.030 (6)	0.023 (6)	0.088 (16)	0.008 (5)	−0.010 (7)	0.004 (7)
C2	0.030 (6)	0.022 (6)	0.076 (17)	0.005 (5)	−0.007 (9)	−0.003 (7)
C3	0.035 (6)	0.029 (6)	0.080 (18)	0.007 (5)	−0.001 (8)	−0.009 (8)
C4	0.033 (6)	0.023 (6)	0.086 (17)	−0.002 (5)	0.006 (7)	−0.002 (7)
C5	0.030 (6)	0.022 (6)	0.084 (17)	0.002 (4)	0.001 (7)	0.009 (7)
C6	0.024 (5)	0.017 (5)	0.082 (14)	0.003 (4)	−0.003 (6)	0.003 (6)
C7	0.023 (6)	0.020 (5)	0.081 (15)	0.004 (4)	−0.011 (7)	0.005 (7)
C8	0.030 (6)	0.029 (6)	0.085 (17)	−0.003 (6)	−0.001 (9)	−0.002 (8)
C9	0.039 (7)	0.036 (6)	0.108 (19)	0.003 (6)	0.008 (10)	0.003 (9)
C10	0.027 (6)	0.027 (6)	0.092 (17)	0.002 (5)	0.000 (8)	0.000 (7)
C11	0.029 (5)	0.022 (5)	0.07 (2)	0.006 (4)	0.004 (7)	0.006 (8)
C12	0.034 (6)	0.027 (5)	0.06 (3)	0.002 (4)	0.002 (8)	0.014 (10)
C13	0.042 (8)	0.038 (8)	0.10 (3)	0.003 (6)	0.016 (12)	0.024 (12)
C14	0.053 (8)	0.028 (6)	0.13 (3)	0.013 (6)	0.026 (13)	0.008 (11)
C15	0.042 (7)	0.033 (7)	0.10 (2)	−0.001 (6)	0.018 (10)	−0.014 (10)

Geometric parameters (Å, º) top

O1—O2	1.464 (16)	C7—C8	1.52 (2)
O1—C4	1.435 (13)	C7—C11	1.549 (15)
O2—C6	1.47 (3)	C8—H8A	0.9700
O3—C4	1.42 (3)	C8—H8B	0.9700
O3—C5	1.40 (2)	C8—C9	1.520 (17)
O4—C5	1.467 (15)	C9—H9A	0.9700
O4—C12	1.337 (15)	C9—H9B	0.9700
O5—C12	1.213 (16)	C9—C10	1.53 (3)
C1—H1	0.9800	C10—H10	0.9800
C1—C2	1.52 (2)	C10—C14	1.545 (17)
C1—C6	1.547 (16)	C11—H11	0.9800
C1—C10	1.50 (3)	C11—C12	1.489 (16)
C2—H2A	0.9700	C11—C13	1.50 (3)
C2—H2B	0.9700	C13—H13A	0.9600
C2—C3	1.52 (2)	C13—H13B	0.9600
C3—H3A	0.9700	C13—H13C	0.9600
C3—H3B	0.9700	C14—H14A	0.9600
C3—C4	1.516 (18)	C14—H14B	0.9600
C4—C15	1.494 (17)	C14—H14C	0.9600
C5—H5	0.9800	C15—H15A	0.9600
C5—C6	1.508 (17)	C15—H15B	0.9600
C6—C7	1.509 (15)	C15—H15C	0.9600
C7—H7	0.9800

C4—O1—O2	108.0 (11)	C7—C8—H8A	109.8
O1—O2—C6	110.3 (12)	C7—C8—H8B	109.8
C5—O3—C4	113.4 (12)	C7—C8—C9	109 (2)
C12—O4—C5	124.6 (10)	H8A—C8—H8B	108.2
C2—C1—H1	107.4	C9—C8—H8A	109.8
C2—C1—C6	112.4 (14)	C9—C8—H8B	109.8
C6—C1—H1	107.4	C8—C9—H9A	108.8
C10—C1—H1	107.4	C8—C9—H9B	108.8
C10—C1—C2	109.5 (13)	C8—C9—C10	113.9 (18)
C10—C1—C6	112.4 (19)	H9A—C9—H9B	107.7
C1—C2—H2A	107.9	C10—C9—H9A	108.8
C1—C2—H2B	107.9	C10—C9—H9B	108.8
H2A—C2—H2B	107.2	C1—C10—C9	113.0 (14)
C3—C2—C1	117.6 (13)	C1—C10—H10	107.6
C3—C2—H2A	107.9	C1—C10—C14	113 (2)
C3—C2—H2B	107.9	C9—C10—H10	107.6
C2—C3—H3A	109.0	C9—C10—C14	107.6 (18)
C2—C3—H3B	109.0	C14—C10—H10	107.6
H3A—C3—H3B	107.8	C7—C11—H11	105.0
C4—C3—C2	112.9 (19)	C12—C11—C7	113.1 (11)
C4—C3—H3A	109.0	C12—C11—H11	105.0
C4—C3—H3B	109.0	C12—C11—C13	113.7 (17)
O1—C4—C3	113.3 (12)	C13—C11—C7	114.0 (16)
O1—C4—C15	104.5 (14)	C13—C11—H11	105.0
O3—C4—O1	106.7 (17)	O4—C12—C11	121.5 (12)
O3—C4—C3	110.8 (15)	O5—C12—O4	115.3 (11)
O3—C4—C15	104.9 (16)	O5—C12—C11	123.2 (13)
C15—C4—C3	115.9 (17)	C11—C13—H13A	109.5
O3—C5—O4	106.8 (14)	C11—C13—H13B	109.5
O3—C5—H5	107.2	C11—C13—H13C	109.5
O3—C5—C6	115.7 (19)	H13A—C13—H13B	109.5
O4—C5—H5	107.2	H13A—C13—H13C	109.5
O4—C5—C6	112.3 (11)	H13B—C13—H13C	109.5
C6—C5—H5	107.2	C10—C14—H14A	109.5
O2—C6—C1	104.1 (16)	C10—C14—H14B	109.5
O2—C6—C5	110.6 (16)	C10—C14—H14C	109.5
O2—C6—C7	106.1 (12)	H14A—C14—H14B	109.5
C5—C6—C1	111.1 (11)	H14A—C14—H14C	109.5
C5—C6—C7	112.1 (15)	H14B—C14—H14C	109.5
C7—C6—C1	112.5 (14)	C4—C15—H15A	109.5
C6—C7—H7	107.5	C4—C15—H15B	109.5
C6—C7—C8	109.8 (13)	C4—C15—H15C	109.5
C6—C7—C11	109.1 (14)	H15A—C15—H15B	109.5
C8—C7—H7	107.5	H15A—C15—H15C	109.5
C8—C7—C11	115.2 (18)	H15B—C15—H15C	109.5
C11—C7—H7	107.5

O1—O2—C6—C1	−109.3 (13)	C5—O3—C4—C3	−88.1 (14)
O1—O2—C6—C5	10.1 (17)	C5—O3—C4—C15	146.2 (11)
O1—O2—C6—C7	131.9 (11)	C5—O4—C12—O5	175 (3)
O2—O1—C4—O3	−76.9 (16)	C5—O4—C12—C11	−5 (4)
O2—O1—C4—C3	45 (3)	C5—C6—C7—C8	−67.4 (17)
O2—O1—C4—C15	172.3 (17)	C5—C6—C7—C11	59.7 (19)
O2—C6—C7—C8	171.8 (11)	C6—C1—C2—C3	−39 (2)
O2—C6—C7—C11	−61.1 (16)	C6—C1—C10—C9	45.1 (16)
O3—C5—C6—O2	−50.3 (17)	C6—C1—C10—C14	167.8 (12)
O3—C5—C6—C1	65 (2)	C6—C7—C8—C9	−59.8 (15)
O3—C5—C6—C7	−168.5 (12)	C6—C7—C11—C12	−45 (3)
O4—C5—C6—O2	73 (2)	C6—C7—C11—C13	−177.1 (16)
O4—C5—C6—C1	−172 (2)	C7—C8—C9—C10	55.4 (19)
O4—C5—C6—C7	−46 (3)	C7—C11—C12—O4	19 (4)
C1—C2—C3—C4	57.5 (18)	C7—C11—C12—O5	−161 (3)
C1—C6—C7—C8	58.6 (17)	C8—C7—C11—C12	79 (3)
C1—C6—C7—C11	−174.3 (19)	C8—C7—C11—C13	−53 (2)
C2—C1—C6—O2	70.3 (16)	C8—C9—C10—C1	−49 (2)
C2—C1—C6—C5	−49 (3)	C8—C9—C10—C14	−174.4 (19)
C2—C1—C6—C7	−175.3 (15)	C10—C1—C2—C3	−164.7 (14)
C2—C1—C10—C9	170.7 (12)	C10—C1—C6—O2	−165.7 (12)
C2—C1—C10—C14	−66.6 (17)	C10—C1—C6—C5	75 (2)
C2—C3—C4—O1	−93 (2)	C10—C1—C6—C7	−51.2 (17)
C2—C3—C4—O3	26.6 (17)	C11—C7—C8—C9	176.6 (12)
C2—C3—C4—C15	146.0 (15)	C12—O4—C5—O3	145 (2)
C4—O1—O2—C6	50 (2)	C12—O4—C5—C6	18 (4)
C4—O3—C5—O4	−100.3 (14)	C13—C11—C12—O4	151 (3)
C4—O3—C5—C6	25.5 (18)	C13—C11—C12—O5	−29 (4)
C5—O3—C4—O1	35.7 (15)

Artemisinin (FormI_3) top

Crystal data top

C₁₅H₂₂O₅	D_x = 1.517 Mg m⁻³
M_r = 282.32	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 1975 reflections
a = 6.0650 (4) Å	θ = 2.5–22.3°
b = 8.8429 (6) Å	µ = 0.11 mm⁻¹
c = 23.048 (4) Å	T = 296 K
V = 1236.1 (2) Å³	Needle, colourless
Z = 4	0.25 × 0.18 × 0.09 mm
F(000) = 608

Data collection top

Bruker APEX-II CCD diffractometer	664 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.044
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0798 before and 0.0536 after correction. The Ratio of minimum to maximum transmission is 0.8644. The λ/2 correction factor is Not present.	θ_max = 23.2°, θ_min = 2.5°
T_min = 0.644, T_max = 0.745	h = −6→6
5447 measured reflections	k = −9→9
747 independent reflections	l = −9→9

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.032	w = 1/[σ²(F_o²) + (0.0348P)² + 0.3482P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.071	(Δ/σ)_max < 0.001
S = 1.12	Δρ_max = 0.12 e Å⁻³
747 reflections	Δρ_min = −0.12 e Å⁻³
184 parameters	Absolute structure: Flack x determined using 238 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
206 restraints	Absolute structure parameter: −0.4 (9)

Special details top

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

	x	y	z	U_iso*/U_eq
O1	0.1903 (6)	0.5645 (4)	0.7340 (4)	0.032 (4)
O2	0.3899 (6)	0.5680 (4)	0.6972 (5)	0.030 (3)
O3	0.0160 (6)	0.3774 (5)	0.6808 (5)	0.035 (3)
O4	−0.0149 (5)	0.5801 (4)	0.6207 (5)	0.042 (5)
O5	−0.0667 (6)	0.8070 (4)	0.5871 (5)	0.041 (6)
C1	0.4952 (9)	0.3378 (7)	0.6499 (7)	0.028 (3)
H1	0.641256	0.367599	0.664071	0.033*
C2	0.3995 (10)	0.2301 (7)	0.6944 (6)	0.033 (4)
H2A	0.514616	0.160221	0.706005	0.040*
H2B	0.284724	0.171295	0.675700	0.040*
C3	0.3017 (9)	0.3014 (6)	0.7496 (6)	0.033 (4)
H3A	0.245805	0.221930	0.774629	0.039*
H3B	0.417273	0.354252	0.770499	0.039*
C4	0.1150 (10)	0.4123 (7)	0.7359 (7)	0.035 (4)
C5	0.1168 (9)	0.4471 (7)	0.6336 (7)	0.032 (4)
H5	0.107468	0.378327	0.600317	0.038*
C6	0.3589 (8)	0.4834 (7)	0.6441 (7)	0.026 (3)
C7	0.4416 (9)	0.5844 (7)	0.5952 (7)	0.027 (4)
H7	0.595847	0.609007	0.603667	0.032*
C8	0.4384 (9)	0.4997 (7)	0.5387 (7)	0.031 (4)
H8A	0.486337	0.565717	0.507579	0.037*
H8B	0.289345	0.466600	0.530270	0.037*
C9	0.5919 (9)	0.3620 (6)	0.5425 (7)	0.034 (4)
H9A	0.586645	0.307458	0.505989	0.041*
H9B	0.742034	0.396727	0.548184	0.041*
C10	0.5312 (10)	0.2560 (7)	0.5910 (7)	0.029 (4)
H10	0.392414	0.206355	0.580410	0.035*
C11	0.3117 (9)	0.7344 (6)	0.5955 (6)	0.025 (5)
H11	0.354250	0.786658	0.631250	0.031*
C12	0.0673 (9)	0.7112 (6)	0.5993 (7)	0.036 (6)
C13	0.3730 (9)	0.8409 (6)	0.5459 (7)	0.035 (5)
H13A	0.530318	0.852210	0.544384	0.052*
H13B	0.305923	0.937788	0.552233	0.052*
H13C	0.321303	0.799541	0.509845	0.052*
C14	0.7065 (11)	0.1321 (6)	0.5992 (7)	0.036 (6)
H14A	0.837853	0.175919	0.615247	0.054*
H14B	0.739982	0.086919	0.562358	0.054*
H14C	0.651095	0.056092	0.625124	0.054*
C15	−0.0685 (10)	0.4160 (6)	0.7798 (8)	0.043 (5)
H15A	−0.009402	0.440360	0.817270	0.065*
H15B	−0.138679	0.318795	0.781300	0.065*
H15C	−0.174573	0.491275	0.768734	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0283 (19)	0.0242 (19)	0.042 (12)	−0.0022 (17)	0.010 (4)	0.000 (3)
O2	0.0248 (19)	0.027 (2)	0.040 (10)	−0.0044 (17)	−0.003 (4)	−0.002 (4)
O3	0.022 (2)	0.028 (2)	0.055 (11)	−0.0061 (18)	0.001 (4)	0.006 (4)
O4	0.0200 (17)	0.030 (2)	0.075 (15)	0.0014 (16)	−0.002 (3)	0.014 (4)
O5	0.034 (2)	0.035 (2)	0.052 (18)	0.0108 (19)	−0.001 (4)	0.007 (4)
C1	0.021 (3)	0.026 (3)	0.036 (11)	0.003 (2)	−0.004 (5)	0.000 (4)
C2	0.032 (3)	0.028 (3)	0.040 (12)	0.002 (3)	0.002 (5)	0.004 (5)
C3	0.030 (3)	0.028 (3)	0.039 (13)	0.002 (3)	−0.001 (5)	0.004 (5)
C4	0.030 (3)	0.022 (3)	0.054 (13)	−0.004 (3)	0.001 (5)	0.002 (5)
C5	0.024 (3)	0.022 (3)	0.049 (13)	0.000 (2)	−0.002 (5)	0.001 (5)
C6	0.019 (2)	0.021 (3)	0.038 (10)	0.001 (2)	0.001 (4)	0.000 (4)
C7	0.021 (3)	0.023 (3)	0.037 (11)	0.001 (2)	−0.007 (5)	−0.002 (4)
C8	0.029 (3)	0.029 (3)	0.035 (13)	−0.003 (3)	−0.002 (6)	0.002 (5)
C9	0.036 (3)	0.028 (3)	0.038 (14)	0.002 (3)	0.002 (6)	0.000 (5)
C10	0.024 (3)	0.028 (3)	0.036 (12)	−0.001 (2)	−0.004 (5)	−0.002 (5)
C11	0.027 (3)	0.023 (3)	0.027 (16)	0.001 (2)	−0.002 (5)	−0.004 (5)
C12	0.028 (3)	0.028 (3)	0.053 (19)	0.002 (2)	−0.004 (5)	0.001 (5)
C13	0.041 (3)	0.027 (3)	0.037 (17)	−0.001 (2)	−0.007 (6)	0.008 (5)
C14	0.038 (3)	0.030 (3)	0.04 (2)	0.007 (3)	0.003 (6)	−0.007 (5)
C15	0.036 (3)	0.027 (3)	0.067 (16)	0.000 (3)	0.015 (6)	0.003 (5)

Geometric parameters (Å, º) top

O1—O2	1.480 (9)	C7—C8	1.501 (17)
O1—C4	1.422 (7)	C7—C11	1.542 (8)
O2—C6	1.445 (15)	C8—H8A	0.9700
O3—C4	1.440 (17)	C8—H8B	0.9700
O3—C5	1.392 (15)	C8—C9	1.535 (7)
O4—C5	1.452 (7)	C9—H9A	0.9700
O4—C12	1.354 (9)	C9—H9B	0.9700
O5—C12	1.207 (7)	C9—C10	1.504 (17)
C1—H1	0.9800	C10—H10	0.9800
C1—C2	1.515 (14)	C10—C14	1.539 (8)
C1—C6	1.536 (8)	C11—H11	0.9800
C1—C10	1.55 (2)	C11—C12	1.499 (7)
C2—H2A	0.9700	C11—C13	1.527 (15)
C2—H2B	0.9700	C13—H13A	0.9600
C2—C3	1.539 (17)	C13—H13B	0.9600
C3—H3A	0.9700	C13—H13C	0.9600
C3—H3B	0.9700	C14—H14A	0.9600
C3—C4	1.530 (9)	C14—H14B	0.9600
C4—C15	1.503 (14)	C14—H14C	0.9600
C5—H5	0.9800	C15—H15A	0.9600
C5—C6	1.523 (8)	C15—H15B	0.9600
C6—C7	1.524 (13)	C15—H15C	0.9600
C7—H7	0.9800

C4—O1—O2	107.5 (6)	C7—C8—H8A	109.7
C6—O2—O1	111.6 (5)	C7—C8—H8B	109.7
C5—O3—C4	114.4 (6)	C7—C8—C9	109.8 (10)
C12—O4—C5	124.4 (5)	H8A—C8—H8B	108.2
C2—C1—H1	106.8	C9—C8—H8A	109.7
C2—C1—C6	112.3 (7)	C9—C8—H8B	109.7
C2—C1—C10	110.7 (6)	C8—C9—H9A	109.0
C6—C1—H1	106.8	C8—C9—H9B	109.0
C6—C1—C10	112.9 (11)	H9A—C9—H9B	107.8
C10—C1—H1	106.8	C10—C9—C8	112.8 (9)
C1—C2—H2A	108.1	C10—C9—H9A	109.0
C1—C2—H2B	108.1	C10—C9—H9B	109.0
C1—C2—C3	116.7 (6)	C1—C10—H10	107.8
H2A—C2—H2B	107.3	C9—C10—C1	113.2 (6)
C3—C2—H2A	108.1	C9—C10—H10	107.8
C3—C2—H2B	108.1	C9—C10—C14	111.5 (8)
C2—C3—H3A	109.2	C14—C10—C1	108.7 (11)
C2—C3—H3B	109.2	C14—C10—H10	107.8
H3A—C3—H3B	107.9	C7—C11—H11	106.0
C4—C3—C2	112.2 (11)	C12—C11—C7	112.8 (5)
C4—C3—H3A	109.2	C12—C11—H11	106.0
C4—C3—H3B	109.2	C12—C11—C13	111.7 (8)
O1—C4—O3	108.0 (10)	C13—C11—C7	113.7 (8)
O1—C4—C3	112.0 (5)	C13—C11—H11	106.0
O1—C4—C15	103.7 (7)	O4—C12—C11	120.2 (6)
O3—C4—C3	110.7 (8)	O5—C12—O4	116.0 (5)
O3—C4—C15	106.8 (7)	O5—C12—C11	123.8 (6)
C15—C4—C3	115.0 (9)	C11—C13—H13A	109.5
O3—C5—O4	106.1 (7)	C11—C13—H13B	109.5
O3—C5—H5	108.1	C11—C13—H13C	109.5
O3—C5—C6	113.1 (11)	H13A—C13—H13B	109.5
O4—C5—H5	108.1	H13A—C13—H13C	109.5
O4—C5—C6	113.1 (5)	H13B—C13—H13C	109.5
C6—C5—H5	108.1	C10—C14—H14A	109.5
O2—C6—C1	106.9 (9)	C10—C14—H14B	109.5
O2—C6—C5	111.7 (9)	C10—C14—H14C	109.5
O2—C6—C7	106.3 (6)	H14A—C14—H14B	109.5
C5—C6—C1	110.9 (5)	H14A—C14—H14C	109.5
C7—C6—C1	112.2 (8)	H14B—C14—H14C	109.5
C7—C6—C5	108.8 (9)	C4—C15—H15A	109.5
C6—C7—H7	107.2	C4—C15—H15B	109.5
C6—C7—C11	109.4 (8)	C4—C15—H15C	109.5
C8—C7—C6	110.1 (6)	H15A—C15—H15B	109.5
C8—C7—H7	107.2	H15A—C15—H15C	109.5
C8—C7—C11	115.2 (10)	H15B—C15—H15C	109.5
C11—C7—H7	107.2

O1—O2—C6—C1	−107.4 (6)	C5—O3—C4—C3	−88.3 (7)
O1—O2—C6—C5	14.0 (10)	C5—O3—C4—C15	145.8 (5)
O1—O2—C6—C7	132.6 (5)	C5—O4—C12—O5	174.9 (13)
O2—O1—C4—O3	−73.7 (8)	C5—O4—C12—C11	−9 (2)
O2—O1—C4—C3	48.5 (14)	C5—C6—C7—C8	−65.6 (8)
O2—O1—C4—C15	173.2 (8)	C5—C6—C7—C11	62.1 (10)
O2—C6—C7—C8	174.0 (5)	C6—C1—C2—C3	−38.2 (12)
O2—C6—C7—C11	−58.4 (8)	C6—C1—C10—C9	44.0 (7)
O3—C5—C6—O2	−52.5 (9)	C6—C1—C10—C14	168.5 (5)
O3—C5—C6—C1	66.5 (13)	C6—C7—C8—C9	−61.3 (7)
O3—C5—C6—C7	−169.5 (7)	C6—C7—C11—C12	−48.3 (14)
O4—C5—C6—O2	68.1 (14)	C6—C7—C11—C13	−176.8 (8)
O4—C5—C6—C1	−172.9 (12)	C7—C8—C9—C10	57.9 (9)
O4—C5—C6—C7	−48.9 (14)	C7—C11—C12—O4	21.6 (19)
C1—C2—C3—C4	58.8 (8)	C7—C11—C12—O5	−162.4 (13)
C1—C6—C7—C8	57.5 (9)	C8—C7—C11—C12	76.5 (13)
C1—C6—C7—C11	−174.8 (9)	C8—C7—C11—C13	−52.1 (9)
C2—C1—C6—O2	69.7 (8)	C8—C9—C10—C1	−48.9 (10)
C2—C1—C6—C5	−52.3 (15)	C8—C9—C10—C14	−171.8 (8)
C2—C1—C6—C7	−174.2 (8)	C10—C1—C2—C3	−165.4 (7)
C2—C1—C10—C9	170.9 (5)	C10—C1—C6—O2	−164.3 (6)
C2—C1—C10—C14	−64.7 (7)	C10—C1—C6—C5	73.7 (12)
C2—C3—C4—O1	−96.5 (11)	C10—C1—C6—C7	−48.2 (8)
C2—C3—C4—O3	24.2 (8)	C11—C7—C8—C9	174.3 (6)
C2—C3—C4—C15	145.3 (7)	C12—O4—C5—O3	147.4 (11)
C4—O1—O2—C6	46.0 (10)	C12—O4—C5—C6	22.9 (18)
C4—O3—C5—O4	−98.0 (7)	C13—C11—C12—O4	151.2 (11)
C4—O3—C5—C6	26.5 (8)	C13—C11—C12—O5	−32.8 (17)
C5—O3—C4—O1	34.8 (7)

Artemisinin (FormI_4) top

Crystal data top

C₁₅H₂₂O₅	D_x = 1.553 Mg m⁻³
M_r = 282.32	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 1760 reflections
a = 6.0225 (4) Å	θ = 2.5–22.5°
b = 8.7906 (6) Å	µ = 0.12 mm⁻¹
c = 22.807 (4) Å	T = 296 K
V = 1207.5 (3) Å³	Needle, colourless
Z = 4	0.25 × 0.18 × 0.09 mm
F(000) = 608

Data collection top

Bruker APEX-II CCD diffractometer	652 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.050
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1200 before and 0.0557 after correction. The Ratio of minimum to maximum transmission is 0.8522. The λ/2 correction factor is Not present.	θ_max = 23.2°, θ_min = 2.5°
T_min = 0.635, T_max = 0.745	h = −6→6
5183 measured reflections	k = −9→9
749 independent reflections	l = −9→9

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.042	w = 1/[σ²(F_o²) + (0.0818P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.116	(Δ/σ)_max < 0.001
S = 1.18	Δρ_max = 0.20 e Å⁻³
749 reflections	Δρ_min = −0.22 e Å⁻³
184 parameters	Absolute structure: Flack x determined using 217 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
206 restraints	Absolute structure parameter: 0.0 (10)

Special details top

Refinement. APEX4

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

	x	y	z	U_iso*/U_eq
O1	0.1879 (8)	0.5640 (5)	0.7342 (6)	0.041 (5)
O2	0.3888 (8)	0.5686 (6)	0.6982 (7)	0.039 (4)
O3	0.0139 (8)	0.3764 (6)	0.6800 (7)	0.038 (4)
O4	−0.0159 (7)	0.5804 (6)	0.6214 (7)	0.048 (6)
O5	−0.0675 (8)	0.8098 (6)	0.5866 (7)	0.054 (7)
C1	0.4961 (12)	0.3364 (9)	0.6498 (8)	0.033 (4)
H1	0.643303	0.365270	0.664330	0.040*
C2	0.3972 (14)	0.2291 (9)	0.6944 (8)	0.038 (4)
H2A	0.281444	0.170620	0.675255	0.045*
H2B	0.511839	0.158085	0.706389	0.045*
C3	0.3001 (12)	0.3000 (8)	0.7487 (8)	0.037 (5)
H3A	0.416561	0.353492	0.769675	0.044*
H3B	0.244867	0.220031	0.774162	0.044*
C4	0.1119 (13)	0.4106 (9)	0.7356 (8)	0.038 (5)
C5	0.1151 (11)	0.4473 (9)	0.6330 (9)	0.034 (5)
H5	0.105313	0.379612	0.598908	0.041*
C6	0.3607 (11)	0.4833 (9)	0.6442 (8)	0.032 (4)
C7	0.4439 (11)	0.5843 (9)	0.5950 (8)	0.033 (4)
H7	0.599349	0.608846	0.603504	0.040*
C8	0.4393 (12)	0.4994 (9)	0.5377 (9)	0.039 (5)
H8A	0.489045	0.565330	0.506238	0.047*
H8B	0.288956	0.466786	0.529054	0.047*
C9	0.5930 (11)	0.3603 (8)	0.5424 (8)	0.037 (5)
H9A	0.588560	0.304733	0.505686	0.045*
H9B	0.744152	0.395095	0.548324	0.045*
C10	0.5313 (13)	0.2539 (9)	0.5916 (9)	0.034 (4)
H10	0.391970	0.203191	0.581058	0.040*
C11	0.3128 (12)	0.7360 (7)	0.5947 (8)	0.032 (6)
H11	0.356830	0.789411	0.630599	0.038*
C12	0.0674 (11)	0.7120 (8)	0.5998 (9)	0.045 (8)
C13	0.3739 (13)	0.8418 (8)	0.5444 (9)	0.042 (6)
H13A	0.531888	0.856323	0.543721	0.063*
H13B	0.301819	0.938227	0.549820	0.063*
H13C	0.326605	0.797719	0.508000	0.063*
C14	0.7114 (14)	0.1296 (8)	0.6007 (10)	0.043 (7)
H14A	0.851212	0.177064	0.609195	0.065*
H14B	0.724739	0.069710	0.565639	0.065*
H14C	0.669421	0.065049	0.632780	0.065*
C15	−0.0738 (12)	0.4161 (9)	0.7787 (9)	0.044 (6)
H15A	−0.015756	0.437221	0.817039	0.066*
H15B	−0.149225	0.319915	0.779116	0.066*
H15C	−0.176249	0.494788	0.767682	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.030 (3)	0.023 (3)	0.071 (14)	−0.002 (2)	0.005 (5)	0.004 (4)
O2	0.025 (2)	0.026 (3)	0.065 (12)	−0.004 (2)	−0.006 (4)	−0.003 (5)
O3	0.022 (3)	0.026 (3)	0.067 (13)	−0.005 (2)	−0.001 (4)	0.004 (4)
O4	0.022 (2)	0.027 (3)	0.095 (19)	0.002 (2)	0.005 (4)	0.016 (5)
O5	0.035 (3)	0.033 (3)	0.09 (2)	0.012 (2)	−0.002 (5)	0.001 (5)
C1	0.025 (4)	0.023 (4)	0.051 (13)	0.005 (3)	−0.008 (5)	0.002 (5)
C2	0.033 (4)	0.023 (4)	0.057 (14)	0.005 (3)	−0.002 (6)	0.003 (6)
C3	0.032 (3)	0.024 (3)	0.055 (15)	0.001 (3)	0.003 (6)	−0.002 (6)
C4	0.027 (3)	0.021 (4)	0.066 (14)	−0.004 (3)	−0.002 (5)	0.005 (5)
C5	0.019 (3)	0.023 (4)	0.059 (14)	−0.001 (3)	0.000 (5)	0.004 (6)
C6	0.016 (3)	0.019 (4)	0.062 (12)	−0.003 (3)	−0.006 (5)	−0.002 (5)
C7	0.016 (3)	0.023 (4)	0.060 (13)	0.001 (3)	−0.009 (5)	−0.002 (5)
C8	0.031 (3)	0.026 (4)	0.061 (14)	−0.003 (3)	−0.002 (7)	−0.003 (6)
C9	0.032 (4)	0.029 (4)	0.050 (15)	0.002 (3)	−0.007 (7)	0.000 (6)
C10	0.025 (4)	0.027 (4)	0.049 (13)	0.000 (3)	−0.012 (6)	0.000 (6)
C11	0.025 (3)	0.018 (3)	0.052 (18)	0.002 (3)	0.003 (5)	−0.003 (6)
C12	0.025 (3)	0.026 (4)	0.08 (2)	0.003 (3)	0.004 (6)	0.007 (7)
C13	0.042 (4)	0.020 (4)	0.065 (19)	0.001 (3)	−0.007 (7)	0.008 (7)
C14	0.043 (4)	0.023 (4)	0.06 (2)	0.006 (3)	0.001 (7)	0.007 (7)
C15	0.033 (4)	0.027 (4)	0.073 (17)	0.000 (3)	0.009 (7)	0.001 (7)

Geometric parameters (Å, º) top

O1—O2	1.463 (11)	C7—C8	1.505 (19)
O1—C4	1.424 (9)	C7—C11	1.550 (10)
O2—C6	1.452 (19)	C8—H8A	0.9700
O3—C4	1.43 (2)	C8—H8B	0.9700
O3—C5	1.383 (18)	C8—C9	1.538 (10)
O4—C5	1.436 (10)	C9—H9A	0.9700
O4—C12	1.354 (11)	C9—H9B	0.9700
O5—C12	1.220 (10)	C9—C10	1.51 (2)
C1—H1	0.9800	C10—H10	0.9800
C1—C2	1.510 (17)	C10—C14	1.554 (11)
C1—C6	1.533 (11)	C11—H11	0.9800
C1—C10	1.53 (2)	C11—C12	1.497 (10)
C2—H2A	0.9700	C11—C13	1.522 (19)
C2—H2B	0.9700	C13—H13A	0.9600
C2—C3	1.51 (2)	C13—H13B	0.9600
C3—H3A	0.9700	C13—H13C	0.9600
C3—H3B	0.9700	C14—H14A	0.9600
C3—C4	1.523 (12)	C14—H14B	0.9600
C4—C15	1.490 (13)	C14—H14C	0.9600
C5—H5	0.9800	C15—H15A	0.9600
C5—C6	1.535 (11)	C15—H15B	0.9600
C6—C7	1.515 (14)	C15—H15C	0.9600
C7—H7	0.9800

C4—O1—O2	107.7 (7)	C7—C8—H8A	109.9
C6—O2—O1	111.4 (7)	C7—C8—H8B	109.9
C5—O3—C4	114.3 (7)	C7—C8—C9	108.8 (13)
C12—O4—C5	124.1 (6)	H8A—C8—H8B	108.3
C2—C1—H1	106.9	C9—C8—H8A	109.9
C2—C1—C6	111.9 (9)	C9—C8—H8B	109.9
C2—C1—C10	110.1 (8)	C8—C9—H9A	108.9
C6—C1—H1	106.9	C8—C9—H9B	108.9
C10—C1—H1	106.9	H9A—C9—H9B	107.7
C10—C1—C6	113.7 (14)	C10—C9—C8	113.4 (11)
C1—C2—H2A	108.1	C10—C9—H9A	108.9
C1—C2—H2B	108.1	C10—C9—H9B	108.9
H2A—C2—H2B	107.3	C1—C10—H10	108.1
C3—C2—C1	116.7 (8)	C1—C10—C14	108.4 (14)
C3—C2—H2A	108.1	C9—C10—C1	112.7 (8)
C3—C2—H2B	108.1	C9—C10—H10	108.1
C2—C3—H3A	109.0	C9—C10—C14	111.3 (10)
C2—C3—H3B	109.0	C14—C10—H10	108.1
C2—C3—C4	113.1 (14)	C7—C11—H11	105.7
H3A—C3—H3B	107.8	C12—C11—C7	112.4 (6)
C4—C3—H3A	109.0	C12—C11—H11	105.7
C4—C3—H3B	109.0	C12—C11—C13	112.5 (11)
O1—C4—O3	108.2 (12)	C13—C11—C7	113.9 (10)
O1—C4—C3	111.7 (7)	C13—C11—H11	105.7
O1—C4—C15	103.0 (9)	O4—C12—C11	120.9 (7)
O3—C4—C3	110.3 (10)	O5—C12—O4	116.4 (6)
O3—C4—C15	106.3 (9)	O5—C12—C11	122.6 (8)
C15—C4—C3	116.7 (11)	C11—C13—H13A	109.5
O3—C5—O4	105.5 (9)	C11—C13—H13B	109.5
O3—C5—H5	108.4	C11—C13—H13C	109.5
O3—C5—C6	112.9 (13)	H13A—C13—H13B	109.5
O4—C5—H5	108.4	H13A—C13—H13C	109.5
O4—C5—C6	113.1 (6)	H13B—C13—H13C	109.5
C6—C5—H5	108.4	C10—C14—H14A	109.5
O2—C6—C1	107.6 (12)	C10—C14—H14B	109.5
O2—C6—C5	111.1 (10)	C10—C14—H14C	109.5
O2—C6—C7	106.7 (7)	H14A—C14—H14B	109.5
C1—C6—C5	110.6 (7)	H14A—C14—H14C	109.5
C7—C6—C1	112.3 (10)	H14B—C14—H14C	109.5
C7—C6—C5	108.4 (10)	C4—C15—H15A	109.5
C6—C7—H7	107.4	C4—C15—H15B	109.5
C6—C7—C11	109.8 (9)	C4—C15—H15C	109.5
C8—C7—C6	110.2 (8)	H15A—C15—H15B	109.5
C8—C7—H7	107.4	H15A—C15—H15C	109.5
C8—C7—C11	114.4 (12)	H15B—C15—H15C	109.5
C11—C7—H7	107.4

O1—O2—C6—C1	−107.0 (8)	C5—O3—C4—C3	−88.0 (9)
O1—O2—C6—C5	14.2 (11)	C5—O3—C4—C15	144.6 (7)
O1—O2—C6—C7	132.3 (7)	C5—O4—C12—O5	172.8 (18)
O2—O1—C4—O3	−74.3 (10)	C5—O4—C12—C11	−9 (3)
O2—O1—C4—C3	47.3 (17)	C5—C6—C7—C8	−65.1 (11)
O2—O1—C4—C15	173.4 (10)	C5—C6—C7—C11	61.8 (12)
O2—C6—C7—C8	175.1 (6)	C6—C1—C2—C3	−37.9 (15)
O2—C6—C7—C11	−58.0 (10)	C6—C1—C10—C9	43.8 (9)
O3—C5—C6—O2	−53.2 (11)	C6—C1—C10—C14	167.5 (6)
O3—C5—C6—C1	66.3 (17)	C6—C7—C8—C9	−61.0 (8)
O3—C5—C6—C7	−170.1 (8)	C6—C7—C11—C12	−46.9 (17)
O4—C5—C6—O2	66.6 (17)	C6—C7—C11—C13	−176.4 (9)
O4—C5—C6—C1	−174.0 (15)	C7—C8—C9—C10	57.8 (11)
O4—C5—C6—C7	−50.4 (17)	C7—C11—C12—O4	20 (3)
C1—C2—C3—C4	59.8 (11)	C7—C11—C12—O5	−162.1 (17)
C1—C6—C7—C8	57.5 (10)	C8—C7—C11—C12	77.7 (16)
C1—C6—C7—C11	−175.6 (12)	C8—C7—C11—C13	−51.8 (11)
C2—C1—C6—O2	69.1 (11)	C8—C9—C10—C1	−49.1 (13)
C2—C1—C6—C5	−52.5 (19)	C8—C9—C10—C14	−171.1 (11)
C2—C1—C6—C7	−173.8 (10)	C10—C1—C2—C3	−165.3 (9)
C2—C1—C10—C9	170.3 (7)	C10—C1—C6—O2	−165.4 (7)
C2—C1—C10—C14	−66.0 (9)	C10—C1—C6—C5	73.0 (15)
C2—C3—C4—O1	−97.0 (13)	C10—C1—C6—C7	−48.3 (10)
C2—C3—C4—O3	23.4 (11)	C11—C7—C8—C9	174.7 (7)
C2—C3—C4—C15	144.8 (9)	C12—O4—C5—O3	148.5 (15)
C4—O1—O2—C6	45.8 (13)	C12—O4—C5—C6	25 (2)
C4—O3—C5—O4	−97.1 (9)	C13—C11—C12—O4	150.5 (14)
C4—O3—C5—C6	26.9 (11)	C13—C11—C12—O5	−32 (2)
C5—O3—C4—O1	34.5 (9)

(FormI_5) top

Crystal data top

C₁₅H₂₂O₅	D_x = 1.573 Mg m⁻³
M_r = 282.32	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 2127 reflections
a = 5.9951 (3) Å	θ = 2.5–22.6°
b = 8.7630 (5) Å	µ = 0.12 mm⁻¹
c = 22.698 (3) Å	T = 296 K
V = 1192.44 (19) Å³	Needle, colourless
Z = 4	0.25 × 0.18 × 0.09 mm
F(000) = 608

Data collection top

Bruker APEX-II CCD diffractometer	669 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.044
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0757 before and 0.0527 after correction. The Ratio of minimum to maximum transmission is 0.8863. The λ/2 correction factor is Not present.	θ_max = 23.3°, θ_min = 2.5°
T_min = 0.660, T_max = 0.745	h = −6→6
5443 measured reflections	k = −9→9
739 independent reflections	l = −9→9

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.031	w = 1/[σ²(F_o²) + (0.0386P)² + 0.2742P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.070	(Δ/σ)_max < 0.001
S = 1.12	Δρ_max = 0.09 e Å⁻³
739 reflections	Δρ_min = −0.15 e Å⁻³
184 parameters	Absolute structure: Flack x determined using 245 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
206 restraints	Absolute structure parameter: 0.0 (9)

Special details top

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

	x	y	z	U_iso*/U_eq
O1	0.1849 (6)	0.5640 (3)	0.7345 (4)	0.031 (4)
O2	0.3884 (6)	0.5687 (4)	0.6978 (5)	0.031 (3)
O3	0.0124 (6)	0.3754 (4)	0.6807 (5)	0.033 (3)
O4	−0.0171 (5)	0.5805 (4)	0.6200 (4)	0.038 (4)
O5	−0.0673 (6)	0.8118 (4)	0.5884 (5)	0.039 (5)
C1	0.4964 (9)	0.3363 (6)	0.6502 (6)	0.026 (3)
H1	0.643980	0.366024	0.664740	0.031*
C2	0.3987 (9)	0.2283 (6)	0.6954 (6)	0.030 (4)
H2A	0.515222	0.158101	0.707437	0.036*
H2B	0.283534	0.168462	0.676212	0.036*
C3	0.2978 (9)	0.2997 (6)	0.7511 (6)	0.030 (4)
H3A	0.241152	0.219231	0.776406	0.036*
H3B	0.413653	0.353441	0.772576	0.036*
C4	0.1086 (10)	0.4107 (6)	0.7368 (7)	0.032 (4)
C5	0.1155 (9)	0.4470 (6)	0.6333 (6)	0.030 (4)
H5	0.107430	0.377984	0.599409	0.037*
C6	0.3600 (8)	0.4831 (6)	0.6445 (6)	0.026 (3)
C7	0.4450 (8)	0.5844 (6)	0.5952 (6)	0.029 (3)
H7	0.601395	0.608226	0.603768	0.034*
C8	0.4394 (9)	0.4986 (6)	0.5372 (6)	0.033 (4)
H8A	0.488017	0.565083	0.505565	0.039*
H8B	0.288242	0.465749	0.528823	0.039*
C9	0.5942 (9)	0.3589 (6)	0.5410 (6)	0.031 (4)
H9A	0.586420	0.302710	0.504253	0.037*
H9B	0.746710	0.393435	0.546097	0.037*
C10	0.5340 (10)	0.2531 (6)	0.5913 (7)	0.028 (3)
H10	0.393924	0.202169	0.580849	0.034*
C11	0.3148 (8)	0.7359 (5)	0.5958 (6)	0.030 (5)
H11	0.358589	0.789209	0.631895	0.036*
C12	0.0670 (8)	0.7134 (6)	0.5994 (7)	0.030 (6)
C13	0.3758 (9)	0.8423 (6)	0.5444 (6)	0.037 (5)
H13A	0.534984	0.852983	0.542295	0.055*
H13B	0.309122	0.940536	0.550590	0.055*
H13C	0.321475	0.799664	0.508145	0.055*
C14	0.7111 (11)	0.1285 (6)	0.6001 (7)	0.036 (6)
H14A	0.846294	0.173877	0.614432	0.054*
H14B	0.739750	0.078790	0.563142	0.054*
H14C	0.657903	0.054961	0.628090	0.054*
C15	−0.0792 (9)	0.4152 (6)	0.7795 (7)	0.038 (5)
H15A	−0.024608	0.446989	0.817357	0.057*
H15B	−0.144057	0.315378	0.782816	0.057*
H15C	−0.190114	0.486043	0.766055	0.057*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0277 (18)	0.0221 (18)	0.045 (11)	−0.0027 (15)	0.009 (4)	0.000 (3)
O2	0.0228 (17)	0.025 (2)	0.045 (10)	−0.0048 (16)	0.001 (3)	−0.004 (3)
O3	0.022 (2)	0.026 (2)	0.049 (10)	−0.0039 (17)	−0.001 (4)	0.006 (3)
O4	0.0209 (17)	0.0271 (19)	0.067 (14)	0.0009 (15)	−0.006 (3)	0.013 (3)
O5	0.033 (2)	0.031 (2)	0.053 (17)	0.0109 (17)	0.001 (4)	0.005 (3)
C1	0.022 (3)	0.025 (3)	0.032 (10)	0.003 (2)	−0.006 (4)	−0.002 (4)
C2	0.030 (3)	0.025 (3)	0.036 (11)	0.004 (2)	0.005 (5)	0.004 (4)
C3	0.029 (2)	0.028 (3)	0.032 (12)	−0.001 (2)	0.000 (5)	0.003 (4)
C4	0.027 (3)	0.020 (3)	0.050 (12)	−0.004 (2)	0.002 (5)	0.002 (4)
C5	0.024 (3)	0.021 (3)	0.046 (13)	0.002 (2)	0.000 (4)	0.002 (4)
C6	0.021 (2)	0.018 (3)	0.041 (10)	−0.002 (2)	−0.001 (4)	−0.002 (4)
C7	0.020 (2)	0.022 (3)	0.044 (11)	0.000 (2)	−0.004 (5)	−0.001 (4)
C8	0.027 (3)	0.026 (3)	0.045 (12)	−0.002 (2)	−0.002 (5)	−0.001 (5)
C9	0.035 (3)	0.028 (3)	0.030 (13)	0.006 (2)	−0.001 (5)	−0.005 (5)
C10	0.029 (3)	0.025 (3)	0.031 (11)	0.000 (2)	−0.004 (5)	0.000 (4)
C11	0.025 (2)	0.019 (2)	0.047 (15)	0.003 (2)	−0.002 (5)	−0.003 (4)
C12	0.027 (3)	0.025 (3)	0.039 (18)	0.003 (2)	−0.001 (5)	−0.003 (4)
C13	0.039 (3)	0.023 (3)	0.048 (16)	0.000 (2)	−0.004 (6)	0.003 (5)
C14	0.041 (3)	0.026 (3)	0.042 (19)	0.007 (2)	−0.001 (6)	0.000 (5)
C15	0.035 (3)	0.025 (3)	0.055 (15)	0.000 (2)	0.011 (6)	0.004 (5)

Geometric parameters (Å, º) top

O1—O2	1.477 (9)	C7—C8	1.516 (13)
O1—C4	1.420 (6)	C7—C11	1.540 (7)
O2—C6	1.434 (15)	C8—H8A	0.9700
O3—C4	1.432 (16)	C8—H8B	0.9700
O3—C5	1.389 (14)	C8—C9	1.539 (7)
O4—C5	1.447 (7)	C9—H9A	0.9700
O4—C12	1.352 (8)	C9—H9B	0.9700
O5—C12	1.206 (6)	C9—C10	1.514 (16)
C1—H1	0.9800	C10—H10	0.9800
C1—C2	1.514 (13)	C10—C14	1.536 (8)
C1—C6	1.530 (8)	C11—H11	0.9800
C1—C10	1.539 (19)	C11—C12	1.501 (7)
C2—H2A	0.9700	C11—C13	1.537 (14)
C2—H2B	0.9700	C13—H13A	0.9600
C2—C3	1.536 (16)	C13—H13B	0.9600
C3—H3A	0.9700	C13—H13C	0.9600
C3—H3B	0.9700	C14—H14A	0.9600
C3—C4	1.530 (8)	C14—H14B	0.9600
C4—C15	1.487 (13)	C14—H14C	0.9600
C5—H5	0.9800	C15—H15A	0.9600
C5—C6	1.521 (8)	C15—H15B	0.9600
C6—C7	1.517 (12)	C15—H15C	0.9600
C7—H7	0.9800

C4—O1—O2	108.2 (5)	C7—C8—H8A	109.8
C6—O2—O1	111.3 (5)	C7—C8—H8B	109.8
C5—O3—C4	114.3 (6)	C7—C8—C9	109.4 (9)
C12—O4—C5	124.3 (4)	H8A—C8—H8B	108.2
C2—C1—H1	106.7	C9—C8—H8A	109.8
C2—C1—C6	112.1 (7)	C9—C8—H8B	109.8
C2—C1—C10	110.4 (6)	C8—C9—H9A	109.1
C6—C1—H1	106.7	C8—C9—H9B	109.1
C6—C1—C10	113.8 (10)	H9A—C9—H9B	107.8
C10—C1—H1	106.7	C10—C9—C8	112.7 (8)
C1—C2—H2A	108.0	C10—C9—H9A	109.1
C1—C2—H2B	108.0	C10—C9—H9B	109.1
C1—C2—C3	117.2 (5)	C1—C10—H10	107.5
H2A—C2—H2B	107.3	C9—C10—C1	113.5 (6)
C3—C2—H2A	108.0	C9—C10—H10	107.5
C3—C2—H2B	108.0	C9—C10—C14	111.6 (8)
C2—C3—H3A	109.2	C14—C10—C1	109.0 (10)
C2—C3—H3B	109.2	C14—C10—H10	107.5
H3A—C3—H3B	107.9	C7—C11—H11	106.4
C4—C3—C2	112.0 (10)	C12—C11—C7	112.9 (4)
C4—C3—H3A	109.2	C12—C11—H11	106.4
C4—C3—H3B	109.2	C12—C11—C13	110.9 (8)
O1—C4—O3	107.6 (9)	C13—C11—C7	113.3 (7)
O1—C4—C3	111.7 (5)	C13—C11—H11	106.4
O1—C4—C15	104.0 (7)	O4—C12—C11	120.1 (5)
O3—C4—C3	110.5 (8)	O5—C12—O4	116.0 (5)
O3—C4—C15	106.3 (7)	O5—C12—C11	123.7 (5)
C15—C4—C3	116.0 (9)	C11—C13—H13A	109.5
O3—C5—O4	106.4 (7)	C11—C13—H13B	109.5
O3—C5—H5	107.9	C11—C13—H13C	109.5
O3—C5—C6	113.2 (10)	H13A—C13—H13B	109.5
O4—C5—H5	107.9	H13A—C13—H13C	109.5
O4—C5—C6	113.3 (4)	H13B—C13—H13C	109.5
C6—C5—H5	107.9	C10—C14—H14A	109.5
O2—C6—C1	107.8 (9)	C10—C14—H14B	109.5
O2—C6—C5	111.4 (8)	C10—C14—H14C	109.5
O2—C6—C7	106.1 (5)	H14A—C14—H14B	109.5
C5—C6—C1	110.7 (5)	H14A—C14—H14C	109.5
C7—C6—C1	112.0 (7)	H14B—C14—H14C	109.5
C7—C6—C5	108.8 (8)	C4—C15—H15A	109.5
C6—C7—H7	107.4	C4—C15—H15B	109.5
C6—C7—C11	109.1 (7)	C4—C15—H15C	109.5
C8—C7—C6	110.1 (6)	H15A—C15—H15B	109.5
C8—C7—H7	107.4	H15A—C15—H15C	109.5
C8—C7—C11	115.1 (8)	H15B—C15—H15C	109.5
C11—C7—H7	107.4

O1—O2—C6—C1	−107.0 (6)	C5—O3—C4—C3	−88.5 (6)
O1—O2—C6—C5	14.6 (9)	C5—O3—C4—C15	144.7 (5)
O1—O2—C6—C7	132.9 (5)	C5—O4—C12—O5	177.3 (12)
O2—O1—C4—O3	−73.5 (7)	C5—O4—C12—C11	−7.3 (18)
O2—O1—C4—C3	48.1 (13)	C5—C6—C7—C8	−64.7 (8)
O2—O1—C4—C15	174.0 (8)	C5—C6—C7—C11	62.5 (9)
O2—C6—C7—C8	175.4 (5)	C6—C1—C2—C3	−37.3 (11)
O2—C6—C7—C11	−57.4 (7)	C6—C1—C10—C9	43.1 (7)
O3—C5—C6—O2	−53.7 (8)	C6—C1—C10—C14	168.2 (5)
O3—C5—C6—C1	66.3 (13)	C6—C7—C8—C9	−61.8 (6)
O3—C5—C6—C7	−170.3 (6)	C6—C7—C11—C12	−48.4 (13)
O4—C5—C6—O2	67.6 (13)	C6—C7—C11—C13	−175.6 (7)
O4—C5—C6—C1	−172.4 (11)	C7—C8—C9—C10	57.0 (8)
O4—C5—C6—C7	−49.0 (13)	C7—C11—C12—O4	20.8 (18)
C1—C2—C3—C4	58.8 (8)	C7—C11—C12—O5	−164.2 (12)
C1—C6—C7—C8	58.0 (8)	C8—C7—C11—C12	75.8 (12)
C1—C6—C7—C11	−174.8 (8)	C8—C7—C11—C13	−51.3 (8)
C2—C1—C6—O2	69.1 (8)	C8—C9—C10—C1	−47.6 (9)
C2—C1—C6—C5	−52.9 (14)	C8—C9—C10—C14	−171.2 (8)
C2—C1—C6—C7	−174.5 (7)	C10—C1—C2—C3	−165.4 (7)
C2—C1—C10—C9	170.2 (5)	C10—C1—C6—O2	−164.6 (6)
C2—C1—C10—C14	−64.7 (6)	C10—C1—C6—C5	73.3 (11)
C2—C3—C4—O1	−96.0 (10)	C10—C1—C6—C7	−48.3 (8)
C2—C3—C4—O3	23.8 (8)	C11—C7—C8—C9	174.4 (5)
C2—C3—C4—C15	145.0 (7)	C12—O4—C5—O3	146.8 (10)
C4—O1—O2—C6	45.8 (10)	C12—O4—C5—C6	21.7 (17)
C4—O3—C5—O4	−97.7 (6)	C13—C11—C12—O4	149.2 (10)
C4—O3—C5—C6	27.5 (8)	C13—C11—C12—O5	−35.8 (16)
C5—O3—C4—O1	33.7 (7)

Artemisinin (FormI_6) top

Crystal data top

C₁₅H₂₂O₅	D_x = 1.597 Mg m⁻³
M_r = 282.32	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 1904 reflections
a = 5.9640 (4) Å	θ = 2.5–22.7°
b = 8.7274 (6) Å	µ = 0.12 mm⁻¹
c = 22.562 (4) Å	T = 296 K
V = 1174.4 (2) Å³	Needle, colourless
Z = 4	0.25 × 0.18 × 0.09 mm
F(000) = 608

Data collection top

Bruker APEX-II CCD diffractometer	643 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.045
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0943 before and 0.0530 after correction. The Ratio of minimum to maximum transmission is 0.8778. The λ/2 correction factor is Not present.	θ_max = 23.2°, θ_min = 2.5°
T_min = 0.654, T_max = 0.745	h = −6→6
5226 measured reflections	k = −9→9
727 independent reflections	l = −9→9

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.031	w = 1/[σ²(F_o²) + (0.0419P)² + 0.0937P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.070	(Δ/σ)_max < 0.001
S = 1.15	Δρ_max = 0.11 e Å⁻³
727 reflections	Δρ_min = −0.14 e Å⁻³
184 parameters	Absolute structure: Flack x determined using 232 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
206 restraints	Absolute structure parameter: −1.6 (10)

Special details top

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

	x	y	z	U_iso*/U_eq
O1	0.1829 (6)	0.5643 (4)	0.7351 (4)	0.031 (4)
O2	0.3870 (6)	0.5690 (4)	0.6983 (5)	0.030 (3)
O3	0.0110 (6)	0.3741 (4)	0.6803 (5)	0.031 (3)
O4	−0.0181 (5)	0.5806 (4)	0.6198 (5)	0.038 (5)
O5	−0.0678 (6)	0.8138 (4)	0.5886 (5)	0.035 (5)
C1	0.4974 (9)	0.3356 (6)	0.6507 (6)	0.024 (3)
H1	0.645527	0.365595	0.665507	0.029*
C2	0.3976 (10)	0.2278 (7)	0.6959 (6)	0.029 (4)
H2A	0.513726	0.156528	0.707952	0.035*
H2B	0.281343	0.168635	0.676414	0.035*
C3	0.2963 (9)	0.2986 (6)	0.7521 (6)	0.029 (4)
H3A	0.239061	0.217661	0.777430	0.035*
H3B	0.412228	0.352761	0.773799	0.035*
C4	0.1061 (10)	0.4097 (6)	0.7370 (7)	0.032 (4)
C5	0.1144 (9)	0.4460 (6)	0.6332 (7)	0.029 (4)
H5	0.106598	0.377139	0.598933	0.035*
C6	0.3597 (9)	0.4822 (7)	0.6447 (6)	0.025 (3)
C7	0.4462 (8)	0.5831 (6)	0.5949 (6)	0.026 (3)
H7	0.603700	0.606282	0.603517	0.031*
C8	0.4395 (9)	0.4970 (6)	0.5368 (6)	0.030 (4)
H8A	0.487685	0.563663	0.504873	0.036*
H8B	0.287283	0.464054	0.528594	0.036*
C9	0.5943 (9)	0.3573 (6)	0.5405 (6)	0.028 (4)
H9A	0.585490	0.300815	0.503511	0.034*
H9B	0.747704	0.392033	0.545269	0.034*
C10	0.5349 (10)	0.2511 (7)	0.5913 (7)	0.027 (3)
H10	0.394033	0.199840	0.580968	0.032*
C11	0.3162 (9)	0.7367 (6)	0.5956 (6)	0.030 (5)
H11	0.361028	0.790486	0.631845	0.036*
C12	0.0671 (9)	0.7143 (6)	0.5993 (7)	0.028 (6)
C13	0.3767 (9)	0.8430 (6)	0.5434 (7)	0.037 (5)
H13A	0.536675	0.853056	0.540822	0.056*
H13B	0.310859	0.942103	0.549671	0.056*
H13C	0.320129	0.800137	0.507172	0.056*
C14	0.7120 (10)	0.1266 (6)	0.6002 (7)	0.029 (6)
H14A	0.847348	0.172079	0.615111	0.044*
H14B	0.742172	0.077191	0.563075	0.044*
H14C	0.657692	0.052374	0.628167	0.044*
C15	−0.0833 (9)	0.4147 (6)	0.7801 (7)	0.037 (5)
H15A	−0.028794	0.447988	0.817995	0.055*
H15B	−0.147671	0.314334	0.783826	0.055*
H15C	−0.195409	0.484992	0.766195	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0257 (18)	0.0212 (19)	0.045 (12)	−0.0032 (15)	0.007 (4)	0.003 (3)
O2	0.0223 (18)	0.024 (2)	0.043 (10)	−0.0052 (16)	0.001 (3)	−0.005 (3)
O3	0.021 (2)	0.025 (2)	0.048 (10)	−0.0051 (17)	0.000 (4)	0.005 (3)
O4	0.0203 (17)	0.0264 (19)	0.068 (15)	0.0018 (15)	−0.005 (3)	0.014 (3)
O5	0.034 (2)	0.030 (2)	0.039 (17)	0.0098 (18)	0.000 (4)	0.005 (3)
C1	0.022 (3)	0.023 (3)	0.027 (11)	0.003 (2)	−0.006 (4)	0.000 (4)
C2	0.028 (3)	0.026 (3)	0.032 (12)	0.006 (2)	0.002 (5)	0.004 (5)
C3	0.027 (2)	0.027 (3)	0.032 (13)	0.002 (3)	0.002 (5)	0.002 (4)
C4	0.027 (3)	0.019 (3)	0.049 (12)	−0.004 (2)	0.003 (5)	0.001 (4)
C5	0.021 (3)	0.021 (3)	0.046 (13)	0.002 (2)	−0.001 (4)	0.001 (4)
C6	0.019 (2)	0.017 (3)	0.040 (10)	−0.001 (2)	0.001 (4)	−0.001 (4)
C7	0.020 (2)	0.019 (3)	0.037 (11)	0.000 (2)	−0.007 (5)	−0.006 (4)
C8	0.025 (3)	0.026 (3)	0.039 (12)	−0.003 (2)	−0.003 (5)	−0.001 (5)
C9	0.033 (3)	0.027 (3)	0.024 (13)	0.005 (2)	−0.004 (5)	−0.003 (5)
C10	0.031 (3)	0.023 (3)	0.027 (11)	0.000 (2)	−0.004 (5)	0.001 (5)
C11	0.026 (3)	0.017 (3)	0.048 (15)	0.001 (2)	0.000 (5)	−0.003 (4)
C12	0.028 (3)	0.024 (3)	0.031 (19)	0.001 (2)	−0.003 (5)	−0.003 (5)
C13	0.037 (3)	0.020 (3)	0.055 (16)	0.003 (2)	0.002 (6)	0.002 (5)
C14	0.039 (3)	0.023 (3)	0.027 (19)	0.003 (2)	0.000 (6)	0.000 (5)
C15	0.033 (3)	0.024 (3)	0.054 (15)	0.001 (2)	0.008 (6)	0.002 (5)

Geometric parameters (Å, º) top

O1—O2	1.474 (9)	C7—C8	1.512 (13)
O1—C4	1.426 (6)	C7—C11	1.549 (7)
O2—C6	1.436 (15)	C8—H8A	0.9700
O3—C4	1.432 (17)	C8—H8B	0.9700
O3—C5	1.381 (15)	C8—C9	1.531 (7)
O4—C5	1.447 (7)	C9—H9A	0.9700
O4—C12	1.354 (8)	C9—H9B	0.9700
O5—C12	1.208 (7)	C9—C10	1.517 (17)
C1—H1	0.9800	C10—H10	0.9800
C1—C2	1.510 (14)	C10—C14	1.528 (8)
C1—C6	1.526 (8)	C11—H11	0.9800
C1—C10	1.547 (19)	C11—C12	1.501 (7)
C2—H2A	0.9700	C11—C13	1.542 (15)
C2—H2B	0.9700	C13—H13A	0.9600
C2—C3	1.535 (16)	C13—H13B	0.9600
C3—H3A	0.9700	C13—H13C	0.9600
C3—H3B	0.9700	C14—H14A	0.9600
C3—C4	1.531 (9)	C14—H14B	0.9600
C4—C15	1.491 (13)	C14—H14C	0.9600
C5—H5	0.9800	C15—H15A	0.9600
C5—C6	1.519 (8)	C15—H15B	0.9600
C6—C7	1.518 (12)	C15—H15C	0.9600
C7—H7	0.9800

C4—O1—O2	108.0 (5)	C7—C8—H8A	109.8
C6—O2—O1	111.5 (5)	C7—C8—H8B	109.8
C5—O3—C4	114.4 (6)	C7—C8—C9	109.5 (9)
C12—O4—C5	124.4 (4)	H8A—C8—H8B	108.2
C2—C1—H1	107.0	C9—C8—H8A	109.8
C2—C1—C6	111.7 (7)	C9—C8—H8B	109.8
C2—C1—C10	110.2 (6)	C8—C9—H9A	109.0
C6—C1—H1	107.0	C8—C9—H9B	109.0
C6—C1—C10	113.6 (11)	H9A—C9—H9B	107.8
C10—C1—H1	107.0	C10—C9—C8	112.7 (9)
C1—C2—H2A	107.9	C10—C9—H9A	109.0
C1—C2—H2B	107.9	C10—C9—H9B	109.0
C1—C2—C3	117.6 (6)	C1—C10—H10	107.4
H2A—C2—H2B	107.2	C9—C10—C1	113.4 (6)
C3—C2—H2A	107.9	C9—C10—H10	107.4
C3—C2—H2B	107.9	C9—C10—C14	111.9 (8)
C2—C3—H3A	109.4	C14—C10—C1	108.9 (11)
C2—C3—H3B	109.4	C14—C10—H10	107.4
H3A—C3—H3B	108.0	C7—C11—H11	106.6
C4—C3—C2	111.2 (11)	C12—C11—C7	112.5 (4)
C4—C3—H3A	109.4	C12—C11—H11	106.6
C4—C3—H3B	109.4	C12—C11—C13	110.7 (8)
O1—C4—O3	107.8 (10)	C13—C11—C7	113.3 (8)
O1—C4—C3	111.6 (5)	C13—C11—H11	106.6
O1—C4—C15	103.6 (7)	O4—C12—C11	120.2 (6)
O3—C4—C3	110.8 (8)	O5—C12—O4	116.0 (5)
O3—C4—C15	106.7 (7)	O5—C12—C11	123.6 (6)
C15—C4—C3	115.7 (9)	C11—C13—H13A	109.5
O3—C5—O4	106.6 (7)	C11—C13—H13B	109.5
O3—C5—H5	107.9	C11—C13—H13C	109.5
O3—C5—C6	113.1 (10)	H13A—C13—H13B	109.5
O4—C5—H5	107.9	H13A—C13—H13C	109.5
O4—C5—C6	113.1 (5)	H13B—C13—H13C	109.5
C6—C5—H5	107.9	C10—C14—H14A	109.5
O2—C6—C1	107.8 (9)	C10—C14—H14B	109.5
O2—C6—C5	111.3 (8)	C10—C14—H14C	109.5
O2—C6—C7	106.2 (5)	H14A—C14—H14B	109.5
C5—C6—C1	111.1 (5)	H14A—C14—H14C	109.5
C7—C6—C1	111.7 (7)	H14B—C14—H14C	109.5
C7—C6—C5	108.8 (8)	C4—C15—H15A	109.5
C6—C7—H7	107.4	C4—C15—H15B	109.5
C6—C7—C11	109.0 (7)	C4—C15—H15C	109.5
C8—C7—C6	110.1 (6)	H15A—C15—H15B	109.5
C8—C7—H7	107.4	H15A—C15—H15C	109.5
C8—C7—C11	115.2 (9)	H15B—C15—H15C	109.5
C11—C7—H7	107.4

O1—O2—C6—C1	−107.0 (6)	C5—O3—C4—C3	−88.8 (6)
O1—O2—C6—C5	15.0 (9)	C5—O3—C4—C15	144.3 (5)
O1—O2—C6—C7	133.2 (5)	C5—O4—C12—O5	177.6 (13)
O2—O1—C4—O3	−73.1 (7)	C5—O4—C12—C11	−7 (2)
O2—O1—C4—C3	48.8 (14)	C5—C6—C7—C8	−64.1 (8)
O2—O1—C4—C15	174.0 (8)	C5—C6—C7—C11	63.1 (9)
O2—C6—C7—C8	176.0 (5)	C6—C1—C2—C3	−38.2 (11)
O2—C6—C7—C11	−56.7 (7)	C6—C1—C10—C9	43.1 (7)
O3—C5—C6—O2	−54.2 (8)	C6—C1—C10—C14	168.5 (5)
O3—C5—C6—C1	65.9 (13)	C6—C7—C8—C9	−62.3 (6)
O3—C5—C6—C7	−170.8 (6)	C6—C7—C11—C12	−48.5 (13)
O4—C5—C6—O2	67.1 (14)	C6—C7—C11—C13	−175.0 (7)
O4—C5—C6—C1	−172.8 (11)	C7—C8—C9—C10	56.9 (9)
O4—C5—C6—C7	−49.5 (13)	C7—C11—C12—O4	20.6 (19)
C1—C2—C3—C4	59.4 (8)	C7—C11—C12—O5	−164.5 (12)
C1—C6—C7—C8	58.8 (8)	C8—C7—C11—C12	75.8 (12)
C1—C6—C7—C11	−174.0 (8)	C8—C7—C11—C13	−50.8 (8)
C2—C1—C6—O2	69.6 (8)	C8—C9—C10—C1	−47.3 (10)
C2—C1—C6—C5	−52.6 (15)	C8—C9—C10—C14	−171.0 (8)
C2—C1—C6—C7	−174.2 (7)	C10—C1—C2—C3	−165.5 (7)
C2—C1—C10—C9	169.4 (5)	C10—C1—C6—O2	−165.0 (6)
C2—C1—C10—C14	−65.2 (7)	C10—C1—C6—C5	72.9 (12)
C2—C3—C4—O1	−96.4 (11)	C10—C1—C6—C7	−48.7 (8)
C2—C3—C4—O3	23.8 (8)	C11—C7—C8—C9	174.0 (5)
C2—C3—C4—C15	145.5 (7)	C12—O4—C5—O3	146.8 (11)
C4—O1—O2—C6	45.3 (10)	C12—O4—C5—C6	21.8 (18)
C4—O3—C5—O4	−97.2 (7)	C13—C11—C12—O4	148.5 (11)
C4—O3—C5—C6	27.8 (8)	C13—C11—C12—O5	−36.6 (17)
C5—O3—C4—O1	33.6 (7)

Artemisinin (FormI_7) top

Crystal data top

C₁₅H₂₂O₅	D_x = 1.639 Mg m⁻³
M_r = 282.32	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 2172 reflections
a = 5.9177 (3) Å	θ = 2.5–22.0°
b = 8.6735 (5) Å	µ = 0.12 mm⁻¹
c = 22.285 (4) Å	T = 296 K
V = 1143.8 (2) Å³	Needle, colourless
Z = 4	0.25 × 0.18 × 0.09 mm
F(000) = 608

Data collection top

Bruker APEX-II CCD diffractometer	536 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.040
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0799 before and 0.0522 after correction. The Ratio of minimum to maximum transmission is 0.8776. The λ/2 correction factor is Not present.	θ_max = 23.2°, θ_min = 2.5°
T_min = 0.654, T_max = 0.745	h = −6→6
5297 measured reflections	k = −9→9
575 independent reflections	l = −6→6

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.027	w = 1/[σ²(F_o²) + (0.0354P)² + 0.3446P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.064	(Δ/σ)_max < 0.001
S = 1.17	Δρ_max = 0.08 e Å⁻³
575 reflections	Δρ_min = −0.11 e Å⁻³
184 parameters	Absolute structure: Flack x determined using 202 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
206 restraints	Absolute structure parameter: −0.5 (9)

Special details top

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

	x	y	z	U_iso*/U_eq
O1	0.1790 (6)	0.5643 (4)	0.7362 (6)	0.035 (5)
O2	0.3861 (7)	0.5690 (5)	0.6984 (8)	0.034 (5)
O3	0.0083 (8)	0.3722 (6)	0.6806 (7)	0.036 (5)
O4	−0.0193 (6)	0.5802 (4)	0.6193 (6)	0.043 (7)
O5	−0.0686 (7)	0.8164 (5)	0.5891 (7)	0.041 (8)
C1	0.4974 (10)	0.3346 (7)	0.6491 (9)	0.034 (5)
H1	0.647145	0.364435	0.663866	0.041*
C2	0.3976 (12)	0.2261 (8)	0.6958 (8)	0.039 (5)
H2A	0.515590	0.155026	0.708030	0.047*
H2B	0.280774	0.165604	0.676398	0.047*
C3	0.2945 (11)	0.2977 (7)	0.7534 (9)	0.037 (5)
H3A	0.236378	0.216519	0.779087	0.044*
H3B	0.410655	0.352851	0.775410	0.044*
C4	0.1025 (12)	0.4090 (8)	0.7367 (10)	0.036 (5)
C5	0.1126 (10)	0.4446 (8)	0.6327 (10)	0.034 (6)
H5	0.105566	0.375515	0.597988	0.041*
C6	0.3594 (10)	0.4822 (8)	0.6448 (8)	0.031 (5)
C7	0.4479 (10)	0.5835 (8)	0.5946 (8)	0.031 (5)
H7	0.606724	0.606436	0.603276	0.037*
C8	0.4402 (11)	0.4961 (8)	0.5359 (9)	0.035 (6)
H8A	0.489044	0.562397	0.503309	0.042*
H8B	0.286828	0.462739	0.527665	0.042*
C9	0.5971 (11)	0.3555 (7)	0.5405 (9)	0.039 (6)
H9A	0.592101	0.298894	0.503017	0.047*
H9B	0.750958	0.390875	0.546426	0.047*
C10	0.5352 (11)	0.2495 (8)	0.5905 (9)	0.036 (5)
H10	0.393191	0.198434	0.579704	0.043*
C11	0.3182 (10)	0.7377 (7)	0.5940 (8)	0.029 (7)
H11	0.364993	0.792024	0.630469	0.035*
C12	0.0663 (10)	0.7149 (7)	0.5999 (9)	0.034 (9)
C13	0.3784 (10)	0.8437 (7)	0.5427 (9)	0.034 (7)
H13A	0.539782	0.852886	0.539929	0.051*
H13B	0.313586	0.943619	0.549607	0.051*
H13C	0.320261	0.802149	0.505861	0.051*
C14	0.7137 (13)	0.1234 (7)	0.6010 (10)	0.039 (9)
H14A	0.847808	0.168945	0.617555	0.058*
H14B	0.749477	0.074471	0.563566	0.058*
H14C	0.655242	0.048051	0.628503	0.058*
C15	−0.0905 (10)	0.4143 (7)	0.7802 (10)	0.037 (6)
H15A	−0.035839	0.444810	0.818936	0.056*
H15B	−0.158535	0.314062	0.782914	0.056*
H15C	−0.200821	0.487402	0.766452	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.023 (2)	0.021 (2)	0.059 (17)	−0.0017 (17)	0.009 (5)	0.005 (4)
O2	0.020 (2)	0.023 (3)	0.059 (16)	−0.0062 (19)	0.002 (4)	−0.002 (5)
O3	0.021 (2)	0.023 (3)	0.065 (15)	−0.005 (2)	0.003 (5)	0.009 (5)
O4	0.0193 (19)	0.022 (2)	0.09 (2)	0.0012 (17)	−0.003 (4)	0.011 (5)
O5	0.031 (2)	0.029 (2)	0.06 (3)	0.010 (2)	−0.002 (5)	0.004 (5)
C1	0.019 (3)	0.021 (3)	0.061 (15)	0.002 (3)	−0.008 (6)	0.000 (6)
C2	0.028 (3)	0.022 (3)	0.066 (16)	0.005 (3)	0.004 (6)	−0.003 (6)
C3	0.026 (3)	0.024 (3)	0.060 (17)	0.002 (3)	−0.003 (6)	−0.003 (6)
C4	0.025 (3)	0.017 (3)	0.066 (16)	−0.004 (3)	0.002 (6)	0.004 (6)
C5	0.021 (3)	0.018 (3)	0.063 (17)	0.002 (2)	0.002 (5)	0.005 (6)
C6	0.017 (3)	0.019 (3)	0.058 (15)	−0.002 (2)	0.000 (5)	−0.003 (5)
C7	0.018 (3)	0.018 (3)	0.058 (16)	0.001 (3)	−0.008 (6)	−0.002 (6)
C8	0.024 (3)	0.022 (3)	0.058 (18)	−0.001 (3)	−0.003 (6)	0.001 (7)
C9	0.030 (3)	0.023 (3)	0.065 (18)	0.003 (3)	0.005 (6)	0.006 (6)
C10	0.024 (3)	0.021 (3)	0.062 (16)	0.002 (3)	−0.005 (6)	0.001 (6)
C11	0.024 (3)	0.017 (3)	0.05 (2)	−0.001 (2)	−0.005 (6)	0.002 (6)
C12	0.025 (3)	0.026 (3)	0.05 (3)	0.003 (3)	−0.004 (6)	−0.001 (7)
C13	0.032 (3)	0.021 (3)	0.05 (2)	0.001 (3)	0.000 (7)	0.001 (7)
C14	0.036 (4)	0.023 (3)	0.06 (3)	0.002 (3)	0.004 (7)	0.008 (7)
C15	0.027 (3)	0.023 (3)	0.06 (2)	−0.001 (3)	0.002 (7)	0.000 (7)

Geometric parameters (Å, º) top

O1—O2	1.488 (12)	C7—C8	1.512 (15)
O1—C4	1.421 (8)	C7—C11	1.543 (9)
O2—C6	1.421 (18)	C8—H8A	0.9700
O3—C4	1.41 (2)	C8—H8B	0.9700
O3—C5	1.38 (2)	C8—C9	1.537 (8)
O4—C5	1.442 (9)	C9—H9A	0.9700
O4—C12	1.345 (10)	C9—H9B	0.9700
O5—C12	1.213 (8)	C9—C10	1.49 (2)
C1—H1	0.9800	C10—H10	0.9800
C1—C2	1.523 (17)	C10—C14	1.538 (10)
C1—C6	1.521 (9)	C11—H11	0.9800
C1—C10	1.52 (2)	C11—C12	1.510 (8)
C2—H2A	0.9700	C11—C13	1.510 (19)
C2—H2B	0.9700	C13—H13A	0.9600
C2—C3	1.55 (2)	C13—H13B	0.9600
C3—H3A	0.9700	C13—H13C	0.9600
C3—H3B	0.9700	C14—H14A	0.9600
C3—C4	1.537 (11)	C14—H14B	0.9600
C4—C15	1.498 (16)	C14—H14C	0.9600
C5—H5	0.9800	C15—H15A	0.9600
C5—C6	1.520 (10)	C15—H15B	0.9600
C6—C7	1.517 (15)	C15—H15C	0.9600
C7—H7	0.9800

C4—O1—O2	107.0 (8)	C7—C8—H8A	109.9
C6—O2—O1	111.7 (7)	C7—C8—H8B	109.9
C5—O3—C4	113.9 (8)	C7—C8—C9	108.7 (12)
C12—O4—C5	124.8 (5)	H8A—C8—H8B	108.3
C2—C1—H1	106.5	C9—C8—H8A	109.9
C2—C1—C6	110.8 (9)	C9—C8—H8B	109.9
C6—C1—H1	106.5	C8—C9—H9A	109.0
C10—C1—H1	106.5	C8—C9—H9B	109.0
C10—C1—C2	110.2 (8)	H9A—C9—H9B	107.8
C10—C1—C6	115.8 (13)	C10—C9—C8	113.1 (11)
C1—C2—H2A	107.8	C10—C9—H9A	109.0
C1—C2—H2B	107.8	C10—C9—H9B	109.0
C1—C2—C3	118.1 (7)	C1—C10—H10	107.8
H2A—C2—H2B	107.1	C1—C10—C14	108.5 (13)
C3—C2—H2A	107.8	C9—C10—C1	112.3 (8)
C3—C2—H2B	107.8	C9—C10—H10	107.8
C2—C3—H3A	109.7	C9—C10—C14	112.6 (9)
C2—C3—H3B	109.7	C14—C10—H10	107.8
H3A—C3—H3B	108.2	C7—C11—H11	105.6
C4—C3—C2	110.0 (14)	C12—C11—C7	112.1 (5)
C4—C3—H3A	109.7	C12—C11—H11	105.6
C4—C3—H3B	109.7	C13—C11—C7	114.7 (10)
O1—C4—C3	111.2 (6)	C13—C11—H11	105.6
O1—C4—C15	102.6 (9)	C13—C11—C12	112.3 (11)
O3—C4—O1	109.6 (13)	O4—C12—C11	120.9 (7)
O3—C4—C3	111.5 (11)	O5—C12—O4	116.6 (6)
O3—C4—C15	106.2 (9)	O5—C12—C11	122.5 (7)
C15—C4—C3	115.2 (13)	C11—C13—H13A	109.5
O3—C5—O4	106.8 (9)	C11—C13—H13B	109.5
O3—C5—H5	108.2	C11—C13—H13C	109.5
O3—C5—C6	112.9 (14)	H13A—C13—H13B	109.5
O4—C5—H5	108.2	H13A—C13—H13C	109.5
O4—C5—C6	112.5 (5)	H13B—C13—H13C	109.5
C6—C5—H5	108.2	C10—C14—H14A	109.5
O2—C6—C1	109.5 (12)	C10—C14—H14B	109.5
O2—C6—C5	111.7 (10)	C10—C14—H14C	109.5
O2—C6—C7	106.0 (7)	H14A—C14—H14B	109.5
C5—C6—C1	110.3 (6)	H14A—C14—H14C	109.5
C7—C6—C1	110.4 (10)	H14B—C14—H14C	109.5
C7—C6—C5	108.9 (11)	C4—C15—H15A	109.5
C6—C7—H7	107.6	C4—C15—H15B	109.5
C6—C7—C11	109.7 (9)	C4—C15—H15C	109.5
C8—C7—C6	109.8 (8)	H15A—C15—H15B	109.5
C8—C7—H7	107.6	H15A—C15—H15C	109.5
C8—C7—C11	114.3 (11)	H15B—C15—H15C	109.5
C11—C7—H7	107.6

O1—O2—C6—C1	−107.3 (8)	C5—O3—C4—C3	−89.6 (8)
O1—O2—C6—C5	15.1 (12)	C5—O3—C4—C15	144.1 (6)
O1—O2—C6—C7	133.7 (7)	C5—O4—C12—O5	178.0 (17)
O2—O1—C4—O3	−72.6 (10)	C5—O4—C12—C11	−4 (3)
O2—O1—C4—C3	51.1 (19)	C5—C6—C7—C8	−63.3 (10)
O2—O1—C4—C15	174.8 (11)	C5—C6—C7—C11	63.1 (12)
O2—C6—C7—C8	176.4 (6)	C6—C1—C2—C3	−36.5 (14)
O2—C6—C7—C11	−57.2 (9)	C6—C1—C10—C9	44.0 (8)
O3—C5—C6—O2	−54.1 (10)	C6—C1—C10—C14	169.0 (6)
O3—C5—C6—C1	67.9 (16)	C6—C7—C8—C9	−62.6 (8)
O3—C5—C6—C7	−170.9 (8)	C6—C7—C11—C12	−45.7 (18)
O4—C5—C6—O2	66.8 (18)	C6—C7—C11—C13	−175.4 (9)
O4—C5—C6—C1	−171.2 (15)	C7—C8—C9—C10	58.5 (11)
O4—C5—C6—C7	−50.0 (18)	C7—C11—C12—O4	16 (3)
C1—C2—C3—C4	58.9 (9)	C7—C11—C12—O5	−165.6 (16)
C1—C6—C7—C8	57.9 (10)	C8—C7—C11—C12	78.0 (15)
C1—C6—C7—C11	−175.7 (11)	C8—C7—C11—C13	−51.6 (10)
C2—C1—C6—O2	68.5 (10)	C8—C9—C10—C1	−48.3 (12)
C2—C1—C6—C5	−54.7 (18)	C8—C9—C10—C14	−171.0 (11)
C2—C1—C6—C7	−175.2 (10)	C10—C1—C2—C3	−165.9 (8)
C2—C1—C10—C9	170.7 (7)	C10—C1—C6—O2	−165.1 (7)
C2—C1—C10—C14	−64.3 (8)	C10—C1—C6—C5	71.6 (15)
C2—C3—C4—O1	−98.2 (14)	C10—C1—C6—C7	−48.8 (10)
C2—C3—C4—O3	24.4 (10)	C11—C7—C8—C9	173.6 (7)
C2—C3—C4—C15	145.6 (9)	C12—O4—C5—O3	145.3 (15)
C4—O1—O2—C6	43.9 (13)	C12—O4—C5—C6	21 (2)
C4—O3—C5—O4	−96.4 (10)	C13—C11—C12—O4	147.1 (14)
C4—O3—C5—C6	27.7 (9)	C13—C11—C12—O5	−35 (2)
C5—O3—C4—O1	34.0 (9)

(FormI_8) top

Crystal data top

C₁₅H₂₂O₅	D_x = 1.639 Mg m⁻³
M_r = 282.32	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 1688 reflections
a = 5.9146 (5) Å	θ = 2.5–22.9°
b = 8.6661 (8) Å	µ = 0.12 mm⁻¹
c = 22.322 (5) Å	T = 296 K
V = 1144.2 (3) Å³	Needle, colourless
Z = 4	0.25 × 0.18 × 0.09 mm
F(000) = 608

Data collection top

Bruker APEX-II CCD diffractometer	549 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.050
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0884 before and 0.0544 after correction. The Ratio of minimum to maximum transmission is 0.8845. The λ/2 correction factor is Not present.	θ_max = 23.2°, θ_min = 2.5°
T_min = 0.659, T_max = 0.745	h = −6→6
5001 measured reflections	k = −9→9
615 independent reflections	l = −7→7

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.030	w = 1/[σ²(F_o²) + (0.0381P)² + 0.3424P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.071	(Δ/σ)_max < 0.001
S = 1.15	Δρ_max = 0.09 e Å⁻³
615 reflections	Δρ_min = −0.13 e Å⁻³
184 parameters	Absolute structure: Flack x determined using 195 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
206 restraints	Absolute structure parameter: −0.6 (10)

Special details top

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

	x	y	z	U_iso*/U_eq
O1	0.1789 (7)	0.5643 (5)	0.7360 (6)	0.040 (5)
O2	0.3858 (7)	0.5687 (6)	0.6987 (7)	0.038 (5)
O3	0.0085 (8)	0.3715 (6)	0.6801 (7)	0.040 (4)
O4	−0.0193 (6)	0.5803 (5)	0.6193 (6)	0.047 (6)
O5	−0.0686 (7)	0.8165 (5)	0.5894 (6)	0.037 (8)
C1	0.4967 (11)	0.3346 (8)	0.6499 (8)	0.035 (5)
H1	0.646248	0.364865	0.664674	0.042*
C2	0.3971 (12)	0.2263 (8)	0.6966 (8)	0.040 (5)
H2A	0.515360	0.155425	0.708837	0.049*
H2B	0.280528	0.165460	0.677201	0.049*
C3	0.2939 (11)	0.2973 (8)	0.7538 (8)	0.039 (5)
H3A	0.234729	0.216079	0.779224	0.047*
H3B	0.409846	0.352204	0.775931	0.047*
C4	0.1027 (12)	0.4092 (8)	0.7367 (9)	0.040 (5)
C5	0.1134 (11)	0.4437 (8)	0.6315 (10)	0.038 (5)
H5	0.106715	0.374978	0.596676	0.046*
C6	0.3590 (11)	0.4820 (8)	0.6448 (8)	0.033 (5)
C7	0.4486 (10)	0.5828 (8)	0.5945 (8)	0.034 (5)
H7	0.607436	0.605784	0.603217	0.041*
C8	0.4404 (11)	0.4964 (8)	0.5354 (8)	0.036 (5)
H8A	0.490125	0.563109	0.503073	0.043*
H8B	0.286880	0.463513	0.526999	0.043*
C9	0.5970 (11)	0.3550 (7)	0.5400 (9)	0.040 (5)
H9A	0.589915	0.297472	0.502822	0.048*
H9B	0.751438	0.390088	0.545311	0.048*
C10	0.5356 (12)	0.2492 (8)	0.5912 (9)	0.037 (5)
H10	0.393741	0.197622	0.580557	0.045*
C11	0.3179 (10)	0.7378 (7)	0.5937 (8)	0.034 (7)
H11	0.364598	0.792391	0.630119	0.041*
C12	0.0673 (10)	0.7154 (8)	0.5995 (9)	0.037 (8)
C13	0.3780 (11)	0.8442 (7)	0.5422 (9)	0.039 (7)
H13A	0.539406	0.853123	0.539268	0.058*
H13B	0.313431	0.944206	0.549101	0.058*
H13C	0.319196	0.802467	0.505491	0.058*
C14	0.7141 (13)	0.1235 (8)	0.6012 (10)	0.041 (9)
H14A	0.847747	0.168816	0.618110	0.062*
H14B	0.750709	0.075789	0.563643	0.062*
H14C	0.655446	0.047080	0.628224	0.062*
C15	−0.0915 (11)	0.4136 (8)	0.7800 (9)	0.040 (6)
H15A	−0.037963	0.445787	0.818594	0.061*
H15B	−0.157383	0.312714	0.783071	0.061*
H15C	−0.203372	0.485294	0.765906	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.025 (2)	0.019 (2)	0.076 (16)	−0.0026 (17)	0.011 (4)	0.006 (4)
O2	0.021 (2)	0.022 (3)	0.071 (14)	−0.006 (2)	0.003 (4)	−0.002 (5)
O3	0.021 (2)	0.023 (3)	0.076 (14)	−0.003 (2)	0.003 (5)	0.004 (5)
O4	0.020 (2)	0.022 (2)	0.098 (19)	0.0011 (18)	−0.005 (4)	0.011 (5)
O5	0.031 (2)	0.030 (3)	0.05 (2)	0.009 (2)	0.000 (5)	−0.004 (5)
C1	0.020 (3)	0.018 (3)	0.067 (15)	0.001 (3)	−0.007 (5)	0.000 (5)
C2	0.028 (3)	0.023 (3)	0.070 (16)	0.005 (3)	0.004 (6)	0.000 (6)
C3	0.027 (3)	0.024 (3)	0.066 (16)	0.002 (3)	−0.001 (6)	0.001 (6)
C4	0.028 (3)	0.017 (3)	0.075 (15)	−0.004 (3)	0.001 (6)	0.002 (6)
C5	0.025 (3)	0.016 (3)	0.073 (16)	0.002 (3)	0.000 (5)	−0.001 (6)
C6	0.017 (3)	0.016 (3)	0.067 (14)	0.001 (3)	−0.001 (5)	−0.001 (5)
C7	0.019 (3)	0.019 (3)	0.064 (15)	0.002 (3)	−0.010 (6)	−0.002 (6)
C8	0.022 (3)	0.021 (3)	0.065 (17)	−0.002 (3)	−0.002 (6)	0.000 (6)
C9	0.028 (3)	0.023 (3)	0.070 (17)	0.005 (3)	0.003 (6)	0.004 (6)
C10	0.028 (3)	0.018 (3)	0.067 (15)	0.002 (3)	−0.002 (6)	−0.001 (6)
C11	0.026 (3)	0.019 (3)	0.06 (2)	0.000 (2)	−0.005 (6)	0.001 (6)
C12	0.024 (3)	0.025 (3)	0.06 (3)	0.002 (3)	−0.001 (6)	−0.004 (7)
C13	0.036 (4)	0.020 (3)	0.06 (2)	0.003 (3)	0.001 (7)	0.002 (7)
C14	0.042 (4)	0.020 (4)	0.06 (3)	0.002 (3)	0.000 (7)	−0.002 (7)
C15	0.030 (3)	0.021 (3)	0.071 (18)	0.003 (3)	−0.001 (7)	0.002 (7)

Geometric parameters (Å, º) top

O1—O2	1.481 (12)	C7—C8	1.517 (15)
O1—C4	1.418 (8)	C7—C11	1.550 (9)
O2—C6	1.428 (18)	C8—H8A	0.9700
O3—C4	1.42 (2)	C8—H8B	0.9700
O3—C5	1.40 (2)	C8—C9	1.539 (8)
O4—C5	1.447 (9)	C9—H9A	0.9700
O4—C12	1.352 (10)	C9—H9B	0.9700
O5—C12	1.211 (8)	C9—C10	1.51 (2)
C1—H1	0.9800	C10—H10	0.9800
C1—C2	1.521 (17)	C10—C14	1.534 (10)
C1—C6	1.519 (9)	C11—H11	0.9800
C1—C10	1.52 (2)	C11—C12	1.500 (9)
C2—H2A	0.9700	C11—C13	1.517 (18)
C2—H2B	0.9700	C13—H13A	0.9600
C2—C3	1.54 (2)	C13—H13B	0.9600
C3—H3A	0.9700	C13—H13C	0.9600
C3—H3B	0.9700	C14—H14A	0.9600
C3—C4	1.538 (11)	C14—H14B	0.9600
C4—C15	1.502 (16)	C14—H14C	0.9600
C5—H5	0.9800	C15—H15A	0.9600
C5—C6	1.519 (11)	C15—H15B	0.9600
C6—C7	1.519 (14)	C15—H15C	0.9600
C7—H7	0.9800

C4—O1—O2	107.1 (7)	C7—C8—H8A	110.0
C6—O2—O1	111.6 (7)	C7—C8—H8B	110.0
C5—O3—C4	114.5 (7)	C7—C8—C9	108.3 (12)
C12—O4—C5	124.4 (5)	H8A—C8—H8B	108.4
C2—C1—H1	106.5	C9—C8—H8A	110.0
C2—C1—C10	110.4 (8)	C9—C8—H8B	110.0
C6—C1—H1	106.5	C8—C9—H9A	109.0
C6—C1—C2	111.2 (9)	C8—C9—H9B	109.0
C6—C1—C10	115.2 (13)	H9A—C9—H9B	107.8
C10—C1—H1	106.5	C10—C9—C8	113.0 (11)
C1—C2—H2A	107.7	C10—C9—H9A	109.0
C1—C2—H2B	107.7	C10—C9—H9B	109.0
C1—C2—C3	118.3 (7)	C1—C10—H10	107.5
H2A—C2—H2B	107.1	C1—C10—C14	108.9 (13)
C3—C2—H2A	107.7	C9—C10—C1	113.1 (7)
C3—C2—H2B	107.7	C9—C10—H10	107.5
C2—C3—H3A	109.7	C9—C10—C14	112.2 (9)
C2—C3—H3B	109.7	C14—C10—H10	107.5
H3A—C3—H3B	108.2	C7—C11—H11	105.6
C4—C3—C2	109.7 (13)	C12—C11—C7	112.3 (6)
C4—C3—H3A	109.7	C12—C11—H11	105.6
C4—C3—H3B	109.7	C12—C11—C13	112.1 (11)
O1—C4—O3	109.5 (13)	C13—C11—C7	114.7 (10)
O1—C4—C3	111.5 (7)	C13—C11—H11	105.6
O1—C4—C15	103.0 (9)	O4—C12—C11	121.0 (7)
O3—C4—C3	111.4 (10)	O5—C12—O4	115.9 (6)
O3—C4—C15	106.2 (9)	O5—C12—C11	123.1 (7)
C15—C4—C3	114.8 (12)	C11—C13—H13A	109.5
O3—C5—O4	105.8 (9)	C11—C13—H13B	109.5
O3—C5—H5	109.0	C11—C13—H13C	109.5
O3—C5—C6	111.7 (14)	H13A—C13—H13B	109.5
O4—C5—H5	109.0	H13A—C13—H13C	109.5
O4—C5—C6	112.1 (6)	H13B—C13—H13C	109.5
C6—C5—H5	109.0	C10—C14—H14A	109.5
O2—C6—C1	108.7 (11)	C10—C14—H14B	109.5
O2—C6—C5	112.7 (10)	C10—C14—H14C	109.5
O2—C6—C7	106.4 (7)	H14A—C14—H14B	109.5
C1—C6—C5	110.1 (6)	H14A—C14—H14C	109.5
C7—C6—C1	110.6 (9)	H14B—C14—H14C	109.5
C7—C6—C5	108.4 (11)	C4—C15—H15A	109.5
C6—C7—H7	107.7	C4—C15—H15B	109.5
C6—C7—C11	109.4 (9)	C4—C15—H15C	109.5
C8—C7—C6	110.4 (8)	H15A—C15—H15B	109.5
C8—C7—H7	107.7	H15A—C15—H15C	109.5
C8—C7—C11	113.7 (11)	H15B—C15—H15C	109.5
C11—C7—H7	107.7

O1—O2—C6—C1	−107.3 (8)	C5—O3—C4—C3	−89.8 (8)
O1—O2—C6—C5	15.1 (12)	C5—O3—C4—C15	144.6 (6)
O1—O2—C6—C7	133.6 (6)	C5—O4—C12—O5	177.3 (17)
O2—O1—C4—O3	−72.7 (10)	C5—O4—C12—C11	−5 (3)
O2—O1—C4—C3	51.0 (18)	C5—C6—C7—C8	−62.0 (10)
O2—O1—C4—C15	174.6 (10)	C5—C6—C7—C11	63.9 (12)
O2—C6—C7—C8	176.6 (6)	C6—C1—C2—C3	−36.8 (14)
O2—C6—C7—C11	−57.6 (9)	C6—C1—C10—C9	43.3 (9)
O3—C5—C6—O2	−53.3 (10)	C6—C1—C10—C14	168.7 (6)
O3—C5—C6—C1	68.2 (16)	C6—C7—C8—C9	−62.7 (8)
O3—C5—C6—C7	−170.7 (8)	C6—C7—C11—C12	−45.7 (18)
O4—C5—C6—O2	65.3 (18)	C6—C7—C11—C13	−175.2 (9)
O4—C5—C6—C1	−173.2 (15)	C7—C8—C9—C10	57.2 (11)
O4—C5—C6—C7	−52.2 (18)	C7—C11—C12—O4	17 (2)
C1—C2—C3—C4	58.4 (9)	C7—C11—C12—O5	−166.4 (15)
C1—C6—C7—C8	58.7 (10)	C8—C7—C11—C12	78.2 (15)
C1—C6—C7—C11	−175.4 (10)	C8—C7—C11—C13	−51.3 (10)
C2—C1—C6—O2	68.3 (10)	C8—C9—C10—C1	−47.4 (12)
C2—C1—C6—C5	−55.5 (18)	C8—C9—C10—C14	−171.0 (11)
C2—C1—C6—C7	−175.2 (10)	C10—C1—C2—C3	−165.9 (9)
C2—C1—C10—C9	170.3 (7)	C10—C1—C6—O2	−165.0 (7)
C2—C1—C10—C14	−64.3 (8)	C10—C1—C6—C5	71.1 (15)
C2—C3—C4—O1	−97.9 (14)	C10—C1—C6—C7	−48.6 (10)
C2—C3—C4—O3	24.8 (10)	C11—C7—C8—C9	173.9 (7)
C2—C3—C4—C15	145.5 (9)	C12—O4—C5—O3	145.6 (14)
C4—O1—O2—C6	44.5 (13)	C12—O4—C5—C6	24 (2)
C4—O3—C5—O4	−95.3 (10)	C13—C11—C12—O4	147.4 (14)
C4—O3—C5—C6	27.0 (9)	C13—C11—C12—O5	−36 (2)
C5—O3—C4—O1	34.0 (9)

(FormII_1) top

Crystal data top

C₁₅H₂₂O₅	Z = 4
M_r = 282.32	F(000) = 608
Triclinic, P1	D_x = 1.277 Mg m⁻³
a = 9.898 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 15.347 (4) Å	Cell parameters from 6845 reflections
c = 9.937 (5) Å	θ = 2.1–23.4°
α = 86.79 (4)°	µ = 0.10 mm⁻¹
β = 102.83 (4)°	T = 296 K
γ = 89.075 (14)°	Plate, clear colourless
V = 1468.8 (9) Å³	0.12 × 0.06 × 0.05 mm

Data collection top

Bruker Photon III diffractometer	2686 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	1019 reflections with I > 2σ(I)
Mirror optics monochromator	R_int = 0.073
Detector resolution: 7.9 pixels mm^-1	θ_max = 23.4°, θ_min = 2.1°
ω scans	h = −10→11
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0785 before and 0.0577 after correction. The Ratio of minimum to maximum transmission is 0.8510. The λ/2 correction factor is Not present.	k = −17→17
T_min = 0.634, T_max = 0.745	l = −5→5
6845 measured 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)] = 0.067	w = 1/[σ²(F_o²) + (0.0661P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.166	(Δ/σ)_max < 0.001
S = 0.96	Δρ_max = 0.10 e Å⁻³
2686 reflections	Δρ_min = −0.12 e Å⁻³
321 parameters	Absolute structure: Flack x determined using 333 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
95 restraints	Absolute structure parameter: 1.0 (10)

Special details top

Refinement. CX-ASAP (Thompson, 2023)

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

	x	y	z	U_iso*/U_eq
O9	0.3365 (18)	0.3111 (9)	0.483 (4)	0.072 (6)*
O8	0.3101 (16)	0.3136 (9)	0.248 (3)	0.071 (5)*
O13	0.4789 (17)	0.7258 (8)	0.674 (3)	0.078 (6)*
O7	0.5143 (18)	0.2353 (10)	0.307 (3)	0.081 (6)*
O20	−0.0948 (15)	0.5666 (8)	0.645 (4)	0.073 (5)*
O12	0.6594 (19)	0.8104 (11)	0.507 (4)	0.082 (7)*
O1	1.0947 (16)	0.0756 (8)	0.361 (4)	0.072 (5)*
O14	0.3992 (16)	0.8066 (8)	0.630 (4)	0.077 (5)*
O15	0.6905 (16)	0.7928 (10)	0.742 (3)	0.071 (5)*
O18	0.1912 (16)	0.5176 (10)	0.766 (4)	0.085 (6)*
O2	1.036 (2)	−0.0085 (10)	0.323 (4)	0.094 (7)*
O19	−0.0374 (19)	0.4777 (9)	0.679 (4)	0.094 (7)*
O6	0.5971 (16)	0.3068 (9)	0.370 (4)	0.083 (5)*
O3	0.8125 (17)	0.0424 (10)	0.252 (4)	0.089 (6)*
O17	0.1585 (19)	0.5360 (11)	0.526 (4)	0.084 (7)*
O11	0.620 (2)	0.8102 (12)	0.278 (4)	0.121 (9)*
O4	0.8448 (19)	0.0425 (11)	0.483 (4)	0.078 (6)*
O16	0.1137 (19)	0.5343 (11)	0.294 (4)	0.111 (8)*
O10	0.364 (2)	0.2884 (12)	0.710 (4)	0.112 (8)*
C16	0.406 (2)	0.2633 (13)	0.192 (3)	0.077 (9)*
O5	0.8864 (18)	0.0194 (12)	0.715 (4)	0.097 (7)*
C9	0.9851 (18)	0.1376 (12)	0.373 (4)	0.054 (7)*
C54	0.0192 (17)	0.6267 (12)	0.644 (4)	0.059 (8)*
C10	0.841 (2)	0.0988 (16)	0.361 (4)	0.075 (9)*
H10	0.768804	0.144814	0.349522	0.090*
C24	0.5113 (19)	0.3839 (12)	0.369 (4)	0.063 (9)*
C46	0.069 (2)	0.4810 (14)	0.800 (3)	0.078 (9)*
C25	0.3601 (19)	0.3625 (16)	0.364 (3)	0.060 (8)*
H25	0.305358	0.417254	0.354003	0.072*
C55	0.161 (2)	0.5795 (16)	0.652 (4)	0.073 (9)*
H55	0.233256	0.622857	0.663743	0.088*
C12	0.911 (3)	0.057 (2)	0.614 (4)	0.124 (17)*
C1	0.929 (3)	0.0085 (16)	0.204 (3)	0.096 (11)*
C8	1.032 (2)	0.1782 (12)	0.511 (4)	0.056 (8)*
H8	1.126530	0.197727	0.512880	0.067*
C3	0.921 (3)	0.1678 (14)	0.118 (5)	0.104 (11)*
H3A	0.944134	0.205783	0.044996	0.125*
H3B	0.820986	0.169548	0.103725	0.125*
C48	0.083 (2)	0.6351 (12)	0.907 (4)	0.086 (10)*
H48A	0.048196	0.664946	0.976170	0.103*
H48B	0.183321	0.636877	0.930638	0.103*
C49	0.030 (2)	0.6847 (13)	0.767 (4)	0.063 (8)*
H49	−0.065543	0.702281	0.765641	0.076*
C40	0.6383 (19)	0.8521 (14)	0.628 (4)	0.056 (8)*
H40	0.695104	0.904090	0.638967	0.068*
C53	−0.030 (2)	0.6808 (13)	0.507 (4)	0.062 (8)*
H53	−0.124947	0.702046	0.504037	0.074*
C50	0.105 (2)	0.7713 (13)	0.755 (5)	0.072 (9)*
H50	0.203397	0.755586	0.764160	0.086*
C19	0.525 (3)	0.4526 (14)	0.255 (4)	0.088 (10)*
H19	0.624794	0.457964	0.263611	0.106*
C32	0.540 (3)	0.7910 (13)	0.898 (4)	0.082 (9)*
H32A	0.593525	0.768888	0.987524	0.098*
H32B	0.444155	0.777253	0.894004	0.098*
C4	0.981 (3)	0.2066 (13)	0.256 (4)	0.066 (8)*
H4	1.077322	0.220987	0.256012	0.079*
C27	0.413 (3)	0.3105 (17)	0.614 (4)	0.086 (12)*
C5	0.903 (2)	0.2929 (13)	0.264 (5)	0.071 (9)*
H5	0.805565	0.278070	0.257387	0.085*
C11	1.047 (3)	0.1058 (18)	0.625 (5)	0.082 (10)*
H11	1.116993	0.063652	0.610138	0.098*
C17	0.477 (3)	0.3193 (12)	0.098 (4)	0.094 (10)*
H17A	0.434192	0.308476	0.002752	0.113*
H17B	0.573066	0.300218	0.114849	0.113*
C23	0.572 (3)	0.4167 (16)	0.512 (4)	0.089 (10)*
H23	0.671482	0.424650	0.518707	0.107*
C33	0.550 (3)	0.8905 (14)	0.890 (5)	0.131 (13)*
H33A	0.647103	0.905099	0.908849	0.157*
H33B	0.510694	0.913308	0.962822	0.157*
C45	0.655 (2)	0.6529 (13)	0.841 (5)	0.098 (10)*
H45A	0.729939	0.659734	0.918699	0.147*
H45B	0.587090	0.615843	0.868336	0.147*
H45C	0.689095	0.627034	0.768775	0.147*
C13	1.097 (3)	0.1370 (16)	0.770 (5)	0.119 (12)*
H13A	1.104008	0.088437	0.836358	0.178*
H13B	1.186385	0.162279	0.777565	0.178*
H13C	1.032388	0.180059	0.786801	0.178*
C7	0.948 (2)	0.2598 (12)	0.524 (5)	0.078 (9)*
H7A	0.984741	0.284011	0.612584	0.094*
H7B	0.852364	0.244784	0.520603	0.094*
C57	0.097 (3)	0.5686 (18)	0.396 (4)	0.094 (13)*
C47	0.040 (2)	0.5390 (12)	0.912 (4)	0.083 (9)*
H47A	0.086886	0.511958	1.000718	0.100*
H47B	−0.058425	0.538445	0.907851	0.100*
C38	0.425 (2)	0.9277 (12)	0.494 (4)	0.065 (8)*
H38	0.325928	0.939208	0.489385	0.078*
C26	0.557 (3)	0.3447 (16)	0.620 (4)	0.079 (10)*
H26	0.613849	0.294866	0.605314	0.095*
C56	−0.038 (3)	0.6216 (17)	0.386 (5)	0.075 (9)*
H56	−0.105636	0.577940	0.398871	0.089*
C22	0.509 (3)	0.5041 (16)	0.537 (5)	0.125 (11)*
H22A	0.410075	0.499116	0.531234	0.149*
H22B	0.551947	0.522232	0.628386	0.149*
C52	0.056 (2)	0.7607 (13)	0.490 (5)	0.084 (10)*
H52A	0.150714	0.742588	0.489980	0.100*
H52B	0.017238	0.793448	0.403648	0.100*
C42	0.583 (3)	0.8312 (17)	0.379 (4)	0.082 (12)*
C6	0.954 (3)	0.3270 (16)	0.407 (5)	0.087 (10)*
H6A	1.048988	0.345013	0.416431	0.105*
H6B	0.898177	0.378102	0.415607	0.105*
C34	0.477 (3)	0.9358 (14)	0.752 (4)	0.077 (9)*
H34	0.378092	0.943885	0.751762	0.093*
C18	0.471 (3)	0.4180 (14)	0.114 (4)	0.121 (13)*
H18A	0.521994	0.445447	0.051157	0.146*
H18B	0.374869	0.437831	0.082357	0.146*
C37	0.492 (3)	1.0141 (14)	0.469 (5)	0.096 (10)*
H37A	0.589285	1.004565	0.469139	0.115*
H37B	0.445941	1.042911	0.381247	0.115*
C14	0.902 (3)	0.3643 (17)	0.150 (5)	0.115 (11)*
H14A	0.869627	0.341107	0.061403	0.173*
H14B	0.842305	0.412031	0.160557	0.173*
H14C	0.994701	0.384556	0.157183	0.173*
C20	0.473 (3)	0.5438 (14)	0.279 (6)	0.099 (11)*
H20	0.372226	0.540479	0.270823	0.119*
C60	0.114 (2)	0.3882 (13)	0.847 (5)	0.092 (9)*
H60A	0.185990	0.387142	0.928902	0.138*
H60B	0.035975	0.356847	0.865488	0.138*
H60C	0.147110	0.361168	0.775002	0.138*
C30	0.339 (2)	0.1832 (14)	0.127 (5)	0.084 (9)*
H30A	0.265510	0.200848	0.049407	0.126*
H30B	0.407382	0.148869	0.096564	0.126*
H30C	0.302583	0.149048	0.193922	0.126*
C51	0.055 (3)	0.8169 (17)	0.612 (5)	0.093 (11)*
H51A	−0.038868	0.839121	0.603798	0.112*
H51B	0.112617	0.866761	0.604292	0.112*
C59	0.100 (2)	0.8324 (15)	0.870 (4)	0.092 (9)*
H59A	0.131961	0.801492	0.958474	0.139*
H59B	0.157712	0.881159	0.862457	0.139*
H59C	0.005966	0.853086	0.861677	0.139*
C35	0.537 (3)	1.0262 (15)	0.732 (6)	0.116 (13)*
H35	0.637782	1.018597	0.742824	0.139*
C58	−0.092 (4)	0.661 (2)	0.239 (5)	0.146 (15)*
H58A	−0.176654	0.694371	0.235137	0.219*
H58B	−0.024565	0.699304	0.214051	0.219*
H58C	−0.110367	0.615685	0.176101	0.219*
C2	0.967 (3)	0.0737 (13)	0.097 (4)	0.103 (10)*
H2A	0.923267	0.057878	0.004983	0.124*
H2B	1.066759	0.071076	0.105855	0.124*
C28	0.617 (3)	0.3703 (16)	0.768 (5)	0.107 (12)*
H28A	0.708525	0.392150	0.773142	0.160*
H28B	0.558827	0.414820	0.791259	0.160*
H28C	0.622152	0.320097	0.830698	0.160*
C21	0.535 (4)	0.5699 (19)	0.426 (6)	0.127 (14)*
H21A	0.634113	0.575917	0.436469	0.153*
H21B	0.495769	0.626380	0.438716	0.153*
C15	0.884 (3)	−0.0779 (17)	0.146 (6)	0.130 (12)*
H15A	0.811017	−0.068086	0.064418	0.195*
H15B	0.961303	−0.107207	0.122547	0.195*
H15C	0.850908	−0.113445	0.213745	0.195*
C44	0.511 (3)	1.0863 (16)	0.842 (5)	0.116 (11)*
H44A	0.549416	1.059384	0.932387	0.174*
H44B	0.554377	1.141012	0.831633	0.174*
H44C	0.413167	1.096071	0.831132	0.174*
C36	0.477 (3)	1.0689 (18)	0.589 (6)	0.106 (11)*
H36A	0.378694	1.081660	0.580855	0.127*
H36B	0.521130	1.124085	0.579341	0.127*
C43	0.383 (3)	0.9043 (18)	0.239 (5)	0.119 (12)*
H43A	0.290125	0.926831	0.231309	0.178*
H43B	0.441285	0.951130	0.222509	0.178*
H43C	0.382596	0.861241	0.173009	0.178*
C29	0.495 (4)	0.611 (2)	0.167 (5)	0.171 (16)*
H29A	0.453524	0.591276	0.077335	0.256*
H29B	0.452206	0.666046	0.178290	0.256*
H29C	0.592225	0.618173	0.174198	0.256*
C39	0.4890 (18)	0.8800 (11)	0.632 (4)	0.048 (7)*
C41	0.438 (3)	0.8627 (19)	0.385 (5)	0.095 (11)*
H41	0.382594	0.811730	0.398014	0.114*
C31	0.588 (2)	0.7409 (13)	0.788 (3)	0.089 (10)*

Geometric parameters (Å, º) top

O9—C27	1.347 (15)	C23—C22	1.529 (14)
O9—C25	1.449 (15)	C23—C26	1.534 (15)
O8—C25	1.412 (14)	C23—H23	0.9800
O8—C16	1.435 (14)	C33—C34	1.530 (15)
O13—C31	1.417 (15)	C33—H33A	0.9700
O13—O14	1.452 (12)	C33—H33B	0.9700
O7—C16	1.420 (14)	C45—C31	1.506 (14)
O7—O6	1.467 (13)	C45—H45A	0.9600
O20—O19	1.462 (12)	C45—H45B	0.9600
O20—C54	1.471 (13)	C45—H45C	0.9600
O12—C42	1.345 (15)	C13—H13A	0.9600
O12—C40	1.448 (14)	C13—H13B	0.9600
O1—C9	1.459 (13)	C13—H13C	0.9600
O1—O2	1.461 (12)	C7—C6	1.524 (15)
O14—C39	1.443 (13)	C7—H7A	0.9700
O15—C40	1.406 (14)	C7—H7B	0.9700
O15—C31	1.436 (14)	C57—C56	1.527 (14)
O18—C55	1.408 (14)	C47—H47A	0.9700
O18—C46	1.442 (13)	C47—H47B	0.9700
O2—C1	1.412 (15)	C38—C39	1.524 (15)
O19—C46	1.416 (15)	C38—C37	1.527 (14)
O6—C24	1.443 (13)	C38—C41	1.536 (15)
O3—C10	1.403 (14)	C38—H38	0.9800
O3—C1	1.442 (14)	C26—C28	1.529 (15)
O17—C57	1.357 (15)	C26—H26	0.9800
O17—C55	1.453 (15)	C56—C58	1.529 (15)
O11—C42	1.205 (15)	C56—H56	0.9800
O4—C12	1.347 (15)	C22—C21	1.525 (15)
O4—C10	1.448 (15)	C22—H22A	0.9700
O16—C57	1.213 (15)	C22—H22B	0.9700
O10—C27	1.205 (15)	C52—C51	1.525 (15)
C16—C30	1.514 (14)	C52—H52A	0.9700
C16—C17	1.526 (15)	C52—H52B	0.9700
O5—C12	1.209 (15)	C42—C41	1.521 (14)
C9—C8	1.515 (15)	C6—H6A	0.9700
C9—C4	1.524 (14)	C6—H6B	0.9700
C9—C10	1.538 (14)	C34—C39	1.529 (14)
C54—C53	1.530 (15)	C34—C35	1.541 (14)
C54—C49	1.535 (14)	C34—H34	0.9800
C54—C55	1.549 (13)	C18—H18A	0.9700
C10—H10	0.9800	C18—H18B	0.9700
C24—C19	1.527 (15)	C37—C36	1.526 (15)
C24—C25	1.530 (14)	C37—H37A	0.9700
C24—C23	1.531 (15)	C37—H37B	0.9700
C46—C60	1.501 (14)	C14—H14A	0.9600
C46—C47	1.529 (15)	C14—H14B	0.9600
C25—H25	0.9800	C14—H14C	0.9600
C55—H55	0.9800	C20—C21	1.529 (15)
C12—C11	1.534 (14)	C20—C29	1.534 (15)
C1—C15	1.510 (14)	C20—H20	0.9800
C1—C2	1.529 (15)	C60—H60A	0.9600
C8—C7	1.523 (13)	C60—H60B	0.9600
C8—C11	1.524 (15)	C60—H60C	0.9600
C8—H8	0.9800	C30—H30A	0.9600
C3—C4	1.526 (15)	C30—H30B	0.9600
C3—C2	1.545 (14)	C30—H30C	0.9600
C3—H3A	0.9700	C51—H51A	0.9700
C3—H3B	0.9700	C51—H51B	0.9700
C48—C49	1.527 (15)	C59—H59A	0.9600
C48—C47	1.543 (13)	C59—H59B	0.9600
C48—H48A	0.9700	C59—H59C	0.9600
C48—H48B	0.9700	C35—C36	1.527 (15)
C49—C50	1.543 (14)	C35—C44	1.529 (15)
C49—H49	0.9800	C35—H35	0.9800
C40—C39	1.542 (13)	C58—H58A	0.9600
C40—H40	0.9800	C58—H58B	0.9600
C53—C52	1.531 (13)	C58—H58C	0.9600
C53—C56	1.538 (15)	C2—H2A	0.9700
C53—H53	0.9800	C2—H2B	0.9700
C50—C59	1.526 (15)	C28—H28A	0.9600
C50—C51	1.529 (15)	C28—H28B	0.9600
C50—H50	0.9800	C28—H28C	0.9600
C19—C18	1.518 (15)	C21—H21A	0.9700
C19—C20	1.533 (14)	C21—H21B	0.9700
C19—H19	0.9800	C15—H15A	0.9600
C32—C31	1.522 (15)	C15—H15B	0.9600
C32—C33	1.529 (13)	C15—H15C	0.9600
C32—H32A	0.9700	C44—H44A	0.9600
C32—H32B	0.9700	C44—H44B	0.9600
C4—C5	1.540 (14)	C44—H44C	0.9600
C4—H4	0.9800	C36—H36A	0.9700
C27—C26	1.516 (14)	C36—H36B	0.9700
C5—C6	1.527 (15)	C43—C41	1.528 (15)
C5—C14	1.529 (15)	C43—H43A	0.9600
C5—H5	0.9800	C43—H43B	0.9600
C11—C13	1.523 (15)	C43—H43C	0.9600
C11—H11	0.9800	C29—H29A	0.9600
C17—C18	1.533 (14)	C29—H29B	0.9600
C17—H17A	0.9700	C29—H29C	0.9600
C17—H17B	0.9700	C41—H41	0.9800

C27—O9—C25	126.6 (18)	C6—C7—H7B	109.7
C25—O8—C16	119.6 (19)	H7A—C7—H7B	108.2
C31—O13—O14	108.9 (18)	O16—C57—O17	122 (3)
C16—O7—O6	113.6 (18)	O16—C57—C56	118 (3)
O19—O20—C54	109.1 (14)	O17—C57—C56	115 (3)
C42—O12—C40	122.8 (18)	C46—C47—C48	118 (3)
C9—O1—O2	110.1 (14)	C46—C47—H47A	107.7
C39—O14—O13	111.1 (16)	C48—C47—H47A	107.7
C40—O15—C31	115.2 (19)	C46—C47—H47B	107.7
C55—O18—C46	113 (2)	C48—C47—H47B	107.7
C1—O2—O1	107 (2)	H47A—C47—H47B	107.1
C46—O19—O20	107 (2)	C39—C38—C37	114 (3)
C24—O6—O7	111.0 (18)	C39—C38—C41	105 (2)
C10—O3—C1	117 (2)	C37—C38—C41	112 (3)
C57—O17—C55	125.2 (18)	C39—C38—H38	108.7
C12—O4—C10	127 (2)	C37—C38—H38	108.7
O7—C16—O8	105.8 (18)	C41—C38—H38	108.7
O7—C16—C30	108 (2)	C27—C26—C28	109 (3)
O8—C16—C30	111 (2)	C27—C26—C23	117 (3)
O7—C16—C17	105 (2)	C28—C26—C23	112 (2)
O8—C16—C17	112 (2)	C27—C26—H26	106.0
C30—C16—C17	114 (2)	C28—C26—H26	106.0
O1—C9—C8	107 (2)	C23—C26—H26	106.0
O1—C9—C4	105 (2)	C57—C56—C58	111 (3)
C8—C9—C4	109.6 (17)	C57—C56—C53	113 (3)
O1—C9—C10	115.1 (17)	C58—C56—C53	118 (2)
C8—C9—C10	111 (2)	C57—C56—H56	104.5
C4—C9—C10	110 (2)	C58—C56—H56	104.5
O20—C54—C53	103 (2)	C53—C56—H56	104.5
O20—C54—C49	108 (2)	C21—C22—C23	107 (3)
C53—C54—C49	110.5 (17)	C21—C22—H22A	110.4
O20—C54—C55	113.4 (15)	C23—C22—H22A	110.4
C53—C54—C55	112 (2)	C21—C22—H22B	110.4
C49—C54—C55	110 (2)	C23—C22—H22B	110.4
O3—C10—O4	104 (2)	H22A—C22—H22B	108.6
O3—C10—C9	111 (2)	C51—C52—C53	107 (3)
O4—C10—C9	108 (2)	C51—C52—H52A	110.2
O3—C10—H10	111.3	C53—C52—H52A	110.2
O4—C10—H10	111.3	C51—C52—H52B	110.2
C9—C10—H10	111.3	C53—C52—H52B	110.2
O6—C24—C19	113 (2)	H52A—C52—H52B	108.5
O6—C24—C25	112.5 (17)	O11—C42—O12	122 (3)
C19—C24—C25	112 (2)	O11—C42—C41	126 (3)
O6—C24—C23	101 (2)	O12—C42—C41	111 (3)
C19—C24—C23	110.4 (19)	C7—C6—C5	113 (2)
C25—C24—C23	107 (3)	C7—C6—H6A	108.9
O19—C46—O18	110 (2)	C5—C6—H6A	108.9
O19—C46—C60	106 (2)	C7—C6—H6B	108.9
O18—C46—C60	103 (2)	C5—C6—H6B	108.9
O19—C46—C47	117 (2)	H6A—C6—H6B	107.8
O18—C46—C47	103 (2)	C39—C34—C33	111 (2)
C60—C46—C47	116 (2)	C39—C34—C35	110 (3)
O8—C25—O9	106 (2)	C33—C34—C35	110 (3)
O8—C25—C24	109 (2)	C39—C34—H34	108.5
O9—C25—C24	115 (2)	C33—C34—H34	108.5
O8—C25—H25	108.8	C35—C34—H34	108.5
O9—C25—H25	108.8	C19—C18—C17	119 (3)
C24—C25—H25	108.8	C19—C18—H18A	107.5
O18—C55—O17	109 (2)	C17—C18—H18A	107.5
O18—C55—C54	111 (2)	C19—C18—H18B	107.5
O17—C55—C54	110 (2)	C17—C18—H18B	107.5
O18—C55—H55	108.8	H18A—C18—H18B	107.0
O17—C55—H55	108.8	C36—C37—C38	105 (3)
C54—C55—H55	108.8	C36—C37—H37A	110.7
O5—C12—O4	124 (3)	C38—C37—H37A	110.7
O5—C12—C11	120 (3)	C36—C37—H37B	110.7
O4—C12—C11	115 (3)	C38—C37—H37B	110.7
O2—C1—O3	106 (2)	H37A—C37—H37B	108.8
O2—C1—C15	108 (3)	C5—C14—H14A	109.5
O3—C1—C15	106 (2)	C5—C14—H14B	109.5
O2—C1—C2	114 (2)	H14A—C14—H14B	109.5
O3—C1—C2	110 (2)	C5—C14—H14C	109.5
C15—C1—C2	113 (2)	H14A—C14—H14C	109.5
C9—C8—C7	113 (2)	H14B—C14—H14C	109.5
C9—C8—C11	108 (2)	C21—C20—C19	111 (3)
C7—C8—C11	117 (3)	C21—C20—C29	113 (2)
C9—C8—H8	105.8	C19—C20—C29	111 (3)
C7—C8—H8	105.8	C21—C20—H20	106.9
C11—C8—H8	105.8	C19—C20—H20	106.9
C4—C3—C2	118 (3)	C29—C20—H20	106.9
C4—C3—H3A	107.8	C46—C60—H60A	109.5
C2—C3—H3A	107.8	C46—C60—H60B	109.5
C4—C3—H3B	107.8	H60A—C60—H60B	109.5
C2—C3—H3B	107.8	C46—C60—H60C	109.5
H3A—C3—H3B	107.2	H60A—C60—H60C	109.5
C49—C48—C47	114 (3)	H60B—C60—H60C	109.5
C49—C48—H48A	108.7	C16—C30—H30A	109.5
C47—C48—H48A	108.7	C16—C30—H30B	109.5
C49—C48—H48B	108.7	H30A—C30—H30B	109.5
C47—C48—H48B	108.7	C16—C30—H30C	109.5
H48A—C48—H48B	107.6	H30A—C30—H30C	109.5
C48—C49—C54	113.2 (19)	H30B—C30—H30C	109.5
C48—C49—C50	112 (3)	C52—C51—C50	116 (2)
C54—C49—C50	116 (2)	C52—C51—H51A	108.4
C48—C49—H49	104.8	C50—C51—H51A	108.4
C54—C49—H49	104.8	C52—C51—H51B	108.4
C50—C49—H49	104.8	C50—C51—H51B	108.4
O15—C40—O12	106.2 (19)	H51A—C51—H51B	107.4
O15—C40—C39	109 (2)	C50—C59—H59A	109.5
O12—C40—C39	118 (2)	C50—C59—H59B	109.5
O15—C40—H40	108.0	H59A—C59—H59B	109.5
O12—C40—H40	108.0	C50—C59—H59C	109.5
C39—C40—H40	108.0	H59A—C59—H59C	109.5
C54—C53—C52	114 (3)	H59B—C59—H59C	109.5
C54—C53—C56	109.4 (19)	C36—C35—C44	109 (2)
C52—C53—C56	111 (3)	C36—C35—C34	112 (3)
C54—C53—H53	107.3	C44—C35—C34	111 (3)
C52—C53—H53	107.3	C36—C35—H35	108.4
C56—C53—H53	107.3	C44—C35—H35	108.4
C59—C50—C51	112.0 (19)	C34—C35—H35	108.4
C59—C50—C49	115 (3)	C56—C58—H58A	109.5
C51—C50—C49	111 (3)	C56—C58—H58B	109.5
C59—C50—H50	106.4	H58A—C58—H58B	109.5
C51—C50—H50	106.4	C56—C58—H58C	109.5
C49—C50—H50	106.4	H58A—C58—H58C	109.5
C18—C19—C24	110 (2)	H58B—C58—H58C	109.5
C18—C19—C20	117 (3)	C1—C2—C3	111 (3)
C24—C19—C20	113 (2)	C1—C2—H2A	109.3
C18—C19—H19	105.1	C3—C2—H2A	109.3
C24—C19—H19	105.1	C1—C2—H2B	109.3
C20—C19—H19	105.1	C3—C2—H2B	109.3
C31—C32—C33	118 (3)	H2A—C2—H2B	108.0
C31—C32—H32A	107.8	C26—C28—H28A	109.5
C33—C32—H32A	107.8	C26—C28—H28B	109.5
C31—C32—H32B	107.8	H28A—C28—H28B	109.5
C33—C32—H32B	107.8	C26—C28—H28C	109.5
H32A—C32—H32B	107.1	H28A—C28—H28C	109.5
C9—C4—C3	110 (2)	H28B—C28—H28C	109.5
C9—C4—C5	116 (2)	C22—C21—C20	113 (3)
C3—C4—C5	109 (3)	C22—C21—H21A	109.0
C9—C4—H4	107.1	C20—C21—H21A	109.0
C3—C4—H4	107.1	C22—C21—H21B	109.0
C5—C4—H4	107.1	C20—C21—H21B	109.0
O10—C27—O9	121 (3)	H21A—C21—H21B	107.8
O10—C27—C26	127 (3)	C1—C15—H15A	109.5
O9—C27—C26	112 (3)	C1—C15—H15B	109.5
C6—C5—C14	111 (2)	H15A—C15—H15B	109.5
C6—C5—C4	109 (3)	C1—C15—H15C	109.5
C14—C5—C4	117 (3)	H15A—C15—H15C	109.5
C6—C5—H5	106.3	H15B—C15—H15C	109.5
C14—C5—H5	106.3	C35—C44—H44A	109.5
C4—C5—H5	106.3	C35—C44—H44B	109.5
C13—C11—C8	114 (3)	H44A—C44—H44B	109.5
C13—C11—C12	111 (3)	C35—C44—H44C	109.5
C8—C11—C12	111 (3)	H44A—C44—H44C	109.5
C13—C11—H11	107.1	H44B—C44—H44C	109.5
C8—C11—H11	107.1	C37—C36—C35	115 (2)
C12—C11—H11	107.1	C37—C36—H36A	108.6
C16—C17—C18	116 (2)	C35—C36—H36A	108.6
C16—C17—H17A	108.3	C37—C36—H36B	108.6
C18—C17—H17A	108.3	C35—C36—H36B	108.6
C16—C17—H17B	108.3	H36A—C36—H36B	107.6
C18—C17—H17B	108.3	C41—C43—H43A	109.5
H17A—C17—H17B	107.4	C41—C43—H43B	109.5
C22—C23—C24	114 (3)	H43A—C43—H43B	109.5
C22—C23—C26	112 (3)	C41—C43—H43C	109.5
C24—C23—C26	108 (2)	H43A—C43—H43C	109.5
C22—C23—H23	107.6	H43B—C43—H43C	109.5
C24—C23—H23	107.6	C20—C29—H29A	109.5
C26—C23—H23	107.6	C20—C29—H29B	109.5
C32—C33—C34	115 (3)	H29A—C29—H29B	109.5
C32—C33—H33A	108.6	C20—C29—H29C	109.5
C34—C33—H33A	108.6	H29A—C29—H29C	109.5
C32—C33—H33B	108.6	H29B—C29—H29C	109.5
C34—C33—H33B	108.6	O14—C39—C38	101 (2)
H33A—C33—H33B	107.6	O14—C39—C34	109 (2)
C31—C45—H45A	109.5	C38—C39—C34	110.8 (16)
C31—C45—H45B	109.5	O14—C39—C40	112.4 (15)
H45A—C45—H45B	109.5	C38—C39—C40	107 (2)
C31—C45—H45C	109.5	C34—C39—C40	115 (2)
H45A—C45—H45C	109.5	C42—C41—C43	102 (3)
H45B—C45—H45C	109.5	C42—C41—C38	118 (3)
C11—C13—H13A	109.5	C43—C41—C38	110 (2)
C11—C13—H13B	109.5	C42—C41—H41	108.7
H13A—C13—H13B	109.5	C43—C41—H41	108.7
C11—C13—H13C	109.5	C38—C41—H41	108.7
H13A—C13—H13C	109.5	O13—C31—O15	109.4 (19)
H13B—C13—H13C	109.5	O13—C31—C45	106 (2)
C8—C7—C6	110 (2)	O15—C31—C45	108 (2)
C8—C7—H7A	109.7	O13—C31—C32	113 (2)
C6—C7—H7A	109.7	O15—C31—C32	107 (2)
C8—C7—H7B	109.7	C45—C31—C32	114 (2)

C31—O13—O14—C39	41 (3)	C7—C8—C11—C12	74 (3)
C9—O1—O2—C1	53 (3)	O5—C12—C11—C13	−28 (4)
C54—O20—O19—C46	51 (3)	O4—C12—C11—C13	167 (3)
C16—O7—O6—C24	36 (3)	O5—C12—C11—C8	−155 (3)
O6—O7—C16—O8	−67 (2)	O4—C12—C11—C8	40 (4)
O6—O7—C16—C30	173.8 (18)	O7—C16—C17—C18	−96 (3)
O6—O7—C16—C17	52 (2)	O8—C16—C17—C18	18 (4)
C25—O8—C16—O7	32 (2)	C30—C16—C17—C18	146 (3)
C25—O8—C16—C30	150 (2)	O6—C24—C23—C22	175 (2)
C25—O8—C16—C17	−81 (3)	C19—C24—C23—C22	56 (3)
O2—O1—C9—C8	130 (2)	C25—C24—C23—C22	−67 (3)
O2—O1—C9—C4	−114 (3)	O6—C24—C23—C26	−60 (2)
O2—O1—C9—C10	7 (4)	C19—C24—C23—C26	−179.4 (19)
O19—O20—C54—C53	131 (2)	C25—C24—C23—C26	58 (2)
O19—O20—C54—C49	−112 (2)	C31—C32—C33—C34	55 (3)
O19—O20—C54—C55	10 (4)	C9—C8—C7—C6	−57 (3)
C1—O3—C10—O4	−96 (2)	C11—C8—C7—C6	176 (2)
C1—O3—C10—C9	20 (3)	C55—O17—C57—O16	170 (2)
C12—O4—C10—O3	156 (3)	C55—O17—C57—C56	−35 (4)
C12—O4—C10—C9	38 (3)	O19—C46—C47—C48	−91 (3)
O1—C9—C10—O3	−44 (4)	O18—C46—C47—C48	30 (3)
C8—C9—C10—O3	−164.7 (18)	C60—C46—C47—C48	142 (3)
C4—C9—C10—O3	74 (3)	C49—C48—C47—C46	51 (3)
O1—C9—C10—O4	70 (4)	O10—C27—C26—C28	−15 (4)
C8—C9—C10—O4	−51 (2)	O9—C27—C26—C28	161 (2)
C4—C9—C10—O4	−172.6 (17)	O10—C27—C26—C23	−143 (3)
O7—O6—C24—C19	−103 (2)	O9—C27—C26—C23	33 (4)
O7—O6—C24—C25	25 (4)	C22—C23—C26—C27	72 (4)
O7—O6—C24—C23	139 (2)	C24—C23—C26—C27	−54 (3)
O20—O19—C46—O18	−77 (2)	C22—C23—C26—C28	−55 (3)
O20—O19—C46—C60	172.0 (19)	C24—C23—C26—C28	179 (2)
O20—O19—C46—C47	40 (2)	O16—C57—C56—C58	−29 (4)
C55—O18—C46—O19	32 (3)	O17—C57—C56—C58	175 (3)
C55—O18—C46—C60	145 (2)	O16—C57—C56—C53	−165 (3)
C55—O18—C46—C47	−94 (2)	O17—C57—C56—C53	40 (3)
C16—O8—C25—O9	−100 (2)	C54—C53—C56—C57	−52 (3)
C16—O8—C25—C24	25 (3)	C52—C53—C56—C57	75 (3)
C27—O9—C25—O8	150 (2)	C54—C53—C56—C58	177 (2)
C27—O9—C25—C24	29 (3)	C52—C53—C56—C58	−56 (3)
O6—C24—C25—O8	−56 (4)	C24—C23—C22—C21	−59 (3)
C19—C24—C25—O8	72 (2)	C26—C23—C22—C21	178 (3)
C23—C24—C25—O8	−166.5 (18)	C54—C53—C52—C51	−57 (3)
O6—C24—C25—O9	63 (4)	C56—C53—C52—C51	178.4 (19)
C19—C24—C25—O9	−169 (2)	C40—O12—C42—O11	164 (2)
C23—C24—C25—O9	−47 (2)	C40—O12—C42—C41	−29 (4)
C46—O18—C55—O17	−92 (2)	C8—C7—C6—C5	57 (3)
C46—O18—C55—C54	30 (3)	C14—C5—C6—C7	176.5 (19)
C57—O17—C55—O18	161 (2)	C4—C5—C6—C7	−53 (3)
C57—O17—C55—C54	39 (3)	C32—C33—C34—C39	−35 (3)
O20—C54—C55—O18	−53 (4)	C32—C33—C34—C35	−158 (2)
C53—C54—C55—O18	−168.7 (19)	C24—C19—C18—C17	−28 (4)
C49—C54—C55—O18	68 (2)	C20—C19—C18—C17	−159 (2)
O20—C54—C55—O17	68 (4)	C16—C17—C18—C19	55 (4)
C53—C54—C55—O17	−48 (2)	C39—C38—C37—C36	−59 (3)
C49—C54—C55—O17	−170.5 (19)	C41—C38—C37—C36	−177 (2)
C10—O4—C12—O5	162 (3)	C18—C19—C20—C21	180 (3)
C10—O4—C12—C11	−34 (4)	C24—C19—C20—C21	50 (3)
O1—O2—C1—O3	−78 (2)	C18—C19—C20—C29	−53 (4)
O1—O2—C1—C15	169 (2)	C24—C19—C20—C29	177 (3)
O1—O2—C1—C2	43 (3)	C53—C52—C51—C50	56 (3)
C10—O3—C1—O2	38 (3)	C59—C50—C51—C52	−180 (2)
C10—O3—C1—C15	153 (3)	C49—C50—C51—C52	−51 (3)
C10—O3—C1—C2	−85 (3)	C39—C34—C35—C36	52 (3)
O1—C9—C8—C7	166 (2)	C33—C34—C35—C36	174 (2)
C4—C9—C8—C7	53 (2)	C39—C34—C35—C44	174 (2)
C10—C9—C8—C7	−68 (3)	C33—C34—C35—C44	−64 (3)
O1—C9—C8—C11	−62 (2)	O2—C1—C2—C3	−93 (3)
C4—C9—C8—C11	−175.2 (16)	O3—C1—C2—C3	25 (3)
C10—C9—C8—C11	63 (2)	C15—C1—C2—C3	143 (3)
C47—C48—C49—C54	−32 (3)	C4—C3—C2—C1	60 (3)
C47—C48—C49—C50	−165 (2)	C23—C22—C21—C20	59 (4)
O20—C54—C49—C48	69 (2)	C19—C20—C21—C22	−56 (3)
C53—C54—C49—C48	−178.6 (17)	C29—C20—C21—C22	178 (2)
C55—C54—C49—C48	−55 (2)	C38—C37—C36—C35	56 (3)
O20—C54—C49—C50	−159 (3)	C44—C35—C36—C37	−178 (2)
C53—C54—C49—C50	−47 (3)	C34—C35—C36—C37	−55 (3)
C55—C54—C49—C50	77 (3)	O13—O14—C39—C38	135 (2)
C31—O15—C40—O12	−98 (2)	O13—O14—C39—C34	−109 (2)
C31—O15—C40—C39	29 (3)	O13—O14—C39—C40	21 (4)
C42—O12—C40—O15	156 (2)	C37—C38—C39—O14	176 (2)
C42—O12—C40—C39	34 (3)	C41—C38—C39—O14	−61 (2)
O20—C54—C53—C52	169 (2)	C37—C38—C39—C34	60 (3)
C49—C54—C53—C52	54 (2)	C41—C38—C39—C34	−177.2 (19)
C55—C54—C53—C52	−69 (3)	C37—C38—C39—C40	−66 (2)
O20—C54—C53—C56	−66 (2)	C41—C38—C39—C40	56 (2)
C49—C54—C53—C56	178.8 (16)	C33—C34—C39—O14	74 (3)
C55—C54—C53—C56	56 (2)	C35—C34—C39—O14	−164 (3)
C48—C49—C50—C59	−55 (3)	C33—C34—C39—C38	−176 (2)
C54—C49—C50—C59	173.0 (19)	C35—C34—C39—C38	−54 (3)
C48—C49—C50—C51	177.3 (19)	C33—C34—C39—C40	−54 (3)
C54—C49—C50—C51	45 (3)	C35—C34—C39—C40	68 (3)
O6—C24—C19—C18	65 (3)	O15—C40—C39—O14	−58 (4)
C25—C24—C19—C18	−63 (3)	O12—C40—C39—O14	63 (4)
C23—C24—C19—C18	177 (2)	O15—C40—C39—C38	−167.9 (17)
O6—C24—C19—C20	−162 (3)	O12—C40—C39—C38	−47 (2)
C25—C24—C19—C20	70 (3)	O15—C40—C39—C34	68 (2)
C23—C24—C19—C20	−50 (3)	O12—C40—C39—C34	−171 (2)
O1—C9—C4—C3	71 (2)	O11—C42—C41—C43	−28 (4)
C8—C9—C4—C3	−174.9 (17)	O12—C42—C41—C43	166 (3)
C10—C9—C4—C3	−53 (2)	O11—C42—C41—C38	−149 (3)
O1—C9—C4—C5	−165 (3)	O12—C42—C41—C38	45 (4)
C8—C9—C4—C5	−50 (3)	C39—C38—C41—C42	−60 (3)
C10—C9—C4—C5	71 (3)	C37—C38—C41—C42	63 (4)
C2—C3—C4—C9	−41 (3)	C39—C38—C41—C43	−177 (2)
C2—C3—C4—C5	−170 (2)	C37—C38—C41—C43	−53 (3)
C25—O9—C27—O10	157 (2)	O14—O13—C31—O15	−71 (2)
C25—O9—C27—C26	−20 (4)	O14—O13—C31—C45	172 (2)
C9—C4—C5—C6	50 (3)	O14—O13—C31—C32	47 (2)
C3—C4—C5—C6	175 (2)	C40—O15—C31—O13	32 (3)
C9—C4—C5—C14	178 (2)	C40—O15—C31—C45	147 (2)
C3—C4—C5—C14	−58 (3)	C40—O15—C31—C32	−91 (2)
C9—C8—C11—C13	179 (2)	C33—C32—C31—O13	−93 (3)
C7—C8—C11—C13	−52 (3)	C33—C32—C31—O15	27 (3)
C9—C8—C11—C12	−56 (3)	C33—C32—C31—C45	146 (3)

(FormII_2) top

Crystal data top

C₁₅H₂₂O₅	Z = 4
M_r = 282.32	F(000) = 608
Triclinic, P1	D_x = 1.276 Mg m⁻³
a = 9.900 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 15.342 (4) Å	Cell parameters from 7939 reflections
c = 9.930 (5) Å	θ = 2.1–23.4°
α = 86.75 (4)°	µ = 0.10 mm⁻¹
β = 102.56 (4)°	T = 296 K
γ = 89.144 (14)°	Plate, clear colourless
V = 1469.2 (9) Å³	0.12 × 0.06 × 0.05 mm

Data collection top

Bruker Photon III diffractometer	2792 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	1002 reflections with I > 2σ(I)
Mirror optics monochromator	R_int = 0.086
Detector resolution: 7.9 pixels mm^-1	θ_max = 23.4°, θ_min = 2.1°
ω scans	h = −10→11
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0824 before and 0.0566 after correction. The Ratio of minimum to maximum transmission is 0.8242. The λ/2 correction factor is Not present.	k = −16→17
T_min = 0.614, T_max = 0.745	l = −5→5
7939 measured 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)] = 0.068	w = 1/[σ²(F_o²) + (0.0507P)² + 0.2145P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.153	(Δ/σ)_max < 0.001
S = 0.98	Δρ_max = 0.11 e Å⁻³
2792 reflections	Δρ_min = −0.11 e Å⁻³
321 parameters	Absolute structure: Flack x determined using 333 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
95 restraints	Absolute structure parameter: 1.1 (10)

Special details top

Refinement. CX-ASAP (Thompson, 2023)

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

	x	y	z	U_iso*/U_eq
O9	0.3381 (18)	0.3120 (10)	0.486 (4)	0.077 (6)*
O8	0.3106 (15)	0.3132 (9)	0.254 (3)	0.067 (5)*
O13	0.4801 (18)	0.7251 (9)	0.674 (4)	0.088 (6)*
O7	0.5147 (18)	0.2354 (10)	0.311 (3)	0.082 (6)*
O20	−0.0949 (15)	0.5665 (8)	0.647 (4)	0.071 (5)*
O12	0.6618 (18)	0.8099 (10)	0.506 (4)	0.075 (6)*
O1	1.0950 (16)	0.0749 (9)	0.364 (4)	0.074 (5)*
O14	0.3978 (16)	0.8042 (9)	0.626 (4)	0.074 (5)*
O15	0.6895 (15)	0.7926 (10)	0.741 (3)	0.068 (6)*
O18	0.1898 (16)	0.5188 (10)	0.758 (4)	0.082 (6)*
O2	1.0337 (19)	−0.0087 (10)	0.326 (4)	0.091 (7)*
O19	−0.0362 (18)	0.4777 (9)	0.681 (4)	0.091 (6)*
O6	0.5985 (16)	0.3064 (10)	0.373 (4)	0.079 (5)*
O3	0.8118 (18)	0.0424 (11)	0.254 (4)	0.099 (7)*
O17	0.1583 (19)	0.5360 (11)	0.521 (4)	0.087 (7)*
O11	0.623 (2)	0.8094 (12)	0.280 (4)	0.127 (9)*
O4	0.8455 (18)	0.0414 (10)	0.486 (4)	0.067 (6)*
O16	0.1152 (19)	0.5348 (11)	0.292 (5)	0.110 (9)*
O10	0.365 (2)	0.2878 (12)	0.711 (4)	0.105 (7)*
C16	0.408 (3)	0.2642 (14)	0.196 (3)	0.084 (10)*
O5	0.8888 (19)	0.0196 (12)	0.714 (4)	0.100 (8)*
C9	0.9865 (19)	0.1390 (13)	0.372 (4)	0.057 (8)*
C54	0.0187 (18)	0.6268 (12)	0.642 (4)	0.059 (8)*
C10	0.842 (2)	0.0978 (16)	0.363 (4)	0.076 (10)*
H10	0.769867	0.143503	0.353603	0.091*
C24	0.5142 (18)	0.3839 (12)	0.376 (4)	0.050 (8)*
C46	0.072 (3)	0.4801 (15)	0.801 (3)	0.087 (10)*
C25	0.3619 (19)	0.3630 (16)	0.367 (3)	0.060 (9)*
H25	0.307732	0.417897	0.356857	0.072*
C55	0.160 (2)	0.5803 (15)	0.646 (4)	0.066 (9)*
H55	0.232399	0.623741	0.656893	0.079*
C12	0.907 (3)	0.062 (2)	0.614 (4)	0.129 (18)*
C1	0.928 (3)	0.0087 (17)	0.206 (4)	0.106 (12)*
C8	1.033 (2)	0.1781 (13)	0.511 (4)	0.057 (8)*
H8	1.126991	0.198187	0.514584	0.069*
C3	0.923 (3)	0.1689 (14)	0.113 (5)	0.093 (10)*
H3A	0.952891	0.205309	0.042357	0.112*
H3B	0.822976	0.172417	0.093680	0.112*
C48	0.081 (2)	0.6347 (12)	0.904 (4)	0.073 (9)*
H48A	0.047007	0.664574	0.974374	0.088*
H48B	0.181645	0.636500	0.927965	0.088*
C49	0.029 (2)	0.6852 (13)	0.765 (4)	0.059 (8)*
H49	−0.066446	0.702926	0.764041	0.071*
C40	0.6375 (18)	0.8510 (14)	0.627 (4)	0.048 (8)*
H40	0.693019	0.903544	0.637536	0.057*
C53	−0.030 (2)	0.6810 (13)	0.505 (4)	0.056 (8)*
H53	−0.124450	0.702183	0.503100	0.067*
C50	0.104 (2)	0.7710 (12)	0.748 (5)	0.058 (9)*
H50	0.202018	0.755676	0.756330	0.070*
C19	0.523 (3)	0.4526 (14)	0.262 (4)	0.080 (10)*
H19	0.623070	0.458620	0.270399	0.096*
C32	0.542 (3)	0.7908 (14)	0.901 (4)	0.098 (10)*
H32A	0.600827	0.771797	0.989913	0.117*
H32B	0.448166	0.774848	0.904064	0.117*
C4	0.978 (3)	0.2069 (13)	0.252 (4)	0.066 (8)*
H4	1.073802	0.222847	0.252996	0.079*
C27	0.415 (3)	0.3116 (18)	0.616 (4)	0.095 (13)*
C5	0.900 (2)	0.2926 (13)	0.264 (5)	0.074 (10)*
H5	0.802365	0.278450	0.255585	0.089*
C11	1.046 (3)	0.1067 (19)	0.627 (5)	0.076 (10)*
H11	1.113584	0.062859	0.612343	0.092*
C17	0.479 (3)	0.3197 (13)	0.101 (4)	0.083 (10)*
H17A	0.434335	0.309854	0.005777	0.099*
H17B	0.574330	0.299751	0.115377	0.099*
C23	0.574 (3)	0.4159 (16)	0.519 (4)	0.094 (11)*
H23	0.673590	0.423823	0.525602	0.113*
C33	0.546 (3)	0.8903 (15)	0.884 (5)	0.111 (12)*
H33A	0.642628	0.906153	0.904521	0.133*
H33B	0.503976	0.914164	0.953709	0.133*
C45	0.656 (2)	0.6534 (13)	0.842 (5)	0.101 (10)*
H45A	0.729780	0.660874	0.920807	0.151*
H45B	0.589007	0.615221	0.868614	0.151*
H45C	0.692577	0.628468	0.770614	0.151*
C13	1.098 (3)	0.1369 (16)	0.773 (5)	0.114 (12)*
H13A	1.102888	0.088090	0.838691	0.171*
H13B	1.187714	0.160976	0.780353	0.171*
H13C	1.034556	0.180680	0.790574	0.171*
C7	0.947 (2)	0.2594 (13)	0.526 (5)	0.077 (9)*
H7A	0.852140	0.243680	0.524422	0.092*
H7B	0.984367	0.284208	0.613957	0.092*
C57	0.094 (3)	0.569 (2)	0.393 (4)	0.115 (16)*
C47	0.039 (2)	0.5390 (12)	0.911 (5)	0.089 (10)*
H47A	0.083962	0.512778	1.001104	0.106*
H47B	−0.059657	0.538217	0.904917	0.106*
C38	0.421 (2)	0.9254 (13)	0.487 (4)	0.059 (8)*
H38	0.322342	0.936109	0.484119	0.071*
C26	0.561 (2)	0.3450 (16)	0.631 (4)	0.072 (10)*
H26	0.618853	0.295153	0.617875	0.086*
C56	−0.041 (2)	0.6205 (16)	0.385 (5)	0.058 (8)*
H56	−0.110793	0.577557	0.396316	0.070*
C22	0.511 (3)	0.5045 (16)	0.536 (5)	0.107 (10)*
H22A	0.554236	0.524874	0.625498	0.128*
H22B	0.413250	0.498800	0.532211	0.128*
C52	0.055 (2)	0.7628 (12)	0.484 (5)	0.071 (9)*
H52A	0.149160	0.745914	0.482390	0.085*
H52B	0.013606	0.795061	0.397739	0.085*
C42	0.581 (3)	0.8298 (16)	0.379 (4)	0.074 (11)*
C6	0.951 (3)	0.3265 (16)	0.408 (5)	0.087 (11)*
H6A	1.045095	0.345502	0.415945	0.105*
H6B	0.894071	0.377091	0.416371	0.105*
C34	0.478 (3)	0.9368 (17)	0.745 (5)	0.097 (10)*
H34	0.379043	0.944851	0.744354	0.116*
C18	0.475 (3)	0.4178 (15)	0.119 (5)	0.130 (14)*
H18A	0.530962	0.444787	0.060133	0.156*
H18B	0.380803	0.438855	0.083773	0.156*
C37	0.488 (3)	1.0131 (15)	0.467 (6)	0.108 (11)*
H37A	0.584688	1.003774	0.465946	0.129*
H37B	0.442031	1.042086	0.378877	0.129*
C14	0.905 (3)	0.3638 (17)	0.151 (5)	0.106 (10)*
H14A	0.872614	0.341048	0.061850	0.159*
H14B	0.846892	0.412628	0.160734	0.159*
H14C	0.998455	0.382243	0.159388	0.159*
C20	0.472 (3)	0.5455 (15)	0.276 (6)	0.103 (12)*
H20	0.371598	0.543699	0.264787	0.124*
C60	0.119 (3)	0.3875 (14)	0.848 (6)	0.111 (10)*
H60A	0.192561	0.387170	0.929158	0.167*
H60B	0.042937	0.355474	0.868919	0.167*
H60C	0.151987	0.360646	0.775708	0.167*
C30	0.341 (2)	0.1836 (14)	0.133 (5)	0.092 (9)*
H30A	0.268028	0.200872	0.054623	0.138*
H30B	0.409080	0.148536	0.103400	0.138*
H30C	0.303395	0.150284	0.200138	0.138*
C51	0.052 (3)	0.8185 (17)	0.606 (5)	0.095 (11)*
H51A	−0.041640	0.839820	0.599319	0.113*
H51B	0.109238	0.868822	0.599177	0.113*
C59	0.096 (2)	0.8311 (16)	0.864 (5)	0.100 (10)*
H59A	0.128512	0.799829	0.951962	0.150*
H59B	0.152010	0.880820	0.857057	0.150*
H59C	0.001384	0.850296	0.855961	0.150*
C35	0.536 (3)	1.0282 (17)	0.729 (6)	0.115 (13)*
H35	0.635763	1.021201	0.737576	0.138*
C58	−0.090 (3)	0.6638 (17)	0.239 (5)	0.113 (13)*
H58A	−0.175295	0.696273	0.234200	0.170*
H58B	−0.021271	0.702603	0.219293	0.170*
H58C	−0.105795	0.619729	0.173173	0.170*
C2	0.968 (3)	0.0738 (12)	0.100 (5)	0.095 (10)*
H2A	0.926880	0.056697	0.008203	0.114*
H2B	1.067996	0.070906	0.110771	0.114*
C28	0.617 (3)	0.3713 (18)	0.779 (5)	0.133 (14)*
H28A	0.709261	0.392264	0.787099	0.199*
H28B	0.558466	0.416646	0.800055	0.199*
H28C	0.618808	0.321561	0.842548	0.199*
C21	0.531 (4)	0.572 (2)	0.423 (6)	0.138 (16)*
H21A	0.488053	0.626593	0.435886	0.166*
H21B	0.629753	0.580971	0.432786	0.166*
C15	0.884 (3)	−0.0813 (17)	0.161 (6)	0.133 (12)*
H15A	0.811719	−0.075618	0.079060	0.199*
H15B	0.961893	−0.112787	0.142241	0.199*
H15C	0.851067	−0.112440	0.233481	0.199*
C44	0.512 (3)	1.0860 (17)	0.843 (6)	0.125 (12)*
H44A	0.552458	1.057693	0.931586	0.188*
H44B	0.555047	1.141108	0.833508	0.188*
H44C	0.414751	1.095443	0.835080	0.188*
C36	0.474 (4)	1.070 (2)	0.585 (6)	0.123 (13)*
H36A	0.376600	1.082874	0.577995	0.148*
H36B	0.519064	1.124376	0.573157	0.148*
C43	0.381 (3)	0.9045 (18)	0.229 (5)	0.125 (13)*
H43A	0.287931	0.926962	0.219767	0.188*
H43B	0.439285	0.951309	0.211603	0.188*
H43C	0.381236	0.861139	0.162782	0.188*
C29	0.500 (4)	0.612 (2)	0.166 (6)	0.196 (18)*
H29A	0.460955	0.593230	0.075617	0.294*
H29B	0.458453	0.667845	0.176648	0.294*
H29C	0.598060	0.618430	0.176094	0.294*
C39	0.4869 (18)	0.8782 (12)	0.627 (4)	0.054 (8)*
C41	0.434 (3)	0.8635 (19)	0.374 (5)	0.089 (11)*
H41	0.377723	0.812760	0.385446	0.107*
C31	0.588 (3)	0.7410 (14)	0.789 (3)	0.090 (11)*

Geometric parameters (Å, º) top

O9—C27	1.341 (15)	C23—C22	1.520 (14)
O9—C25	1.444 (15)	C23—C26	1.537 (15)
O8—C25	1.405 (15)	C23—H23	0.9800
O8—C16	1.444 (14)	C33—C34	1.531 (15)
O13—C31	1.420 (15)	C33—H33A	0.9700
O13—O14	1.450 (13)	C33—H33B	0.9700
O7—C16	1.419 (15)	C45—C31	1.508 (14)
O7—O6	1.460 (13)	C45—H45A	0.9600
O20—O19	1.466 (12)	C45—H45B	0.9600
O20—C54	1.475 (13)	C45—H45C	0.9600
O12—C42	1.351 (15)	C13—H13A	0.9600
O12—C40	1.448 (15)	C13—H13B	0.9600
O1—O2	1.462 (13)	C13—H13C	0.9600
O1—C9	1.463 (13)	C7—C6	1.527 (15)
O14—C39	1.448 (13)	C7—H7A	0.9700
O15—C40	1.403 (15)	C7—H7B	0.9700
O15—C31	1.441 (14)	C57—C56	1.528 (14)
O18—C55	1.397 (15)	C47—H47A	0.9700
O18—C46	1.448 (14)	C47—H47B	0.9700
O2—C1	1.410 (15)	C38—C39	1.530 (15)
O19—C46	1.424 (15)	C38—C37	1.532 (14)
O6—C24	1.448 (13)	C38—C41	1.536 (15)
O3—C10	1.401 (15)	C38—H38	0.9800
O3—C1	1.441 (14)	C26—C28	1.533 (15)
O17—C57	1.356 (15)	C26—H26	0.9800
O17—C55	1.444 (15)	C56—C58	1.528 (15)
O11—C42	1.209 (15)	C56—H56	0.9800
O4—C12	1.342 (15)	C22—C21	1.528 (15)
O4—C10	1.445 (15)	C22—H22A	0.9700
O16—C57	1.215 (15)	C22—H22B	0.9700
O10—C27	1.200 (15)	C52—C51	1.525 (15)
C16—C30	1.516 (14)	C52—H52A	0.9700
C16—C17	1.527 (15)	C52—H52B	0.9700
O5—C12	1.203 (15)	C42—C41	1.523 (14)
C9—C8	1.522 (15)	C6—H6A	0.9700
C9—C4	1.524 (15)	C6—H6B	0.9700
C9—C10	1.558 (14)	C34—C39	1.535 (15)
C54—C53	1.535 (15)	C34—C35	1.536 (14)
C54—C49	1.539 (15)	C34—H34	0.9800
C54—C55	1.551 (13)	C18—H18A	0.9700
C10—H10	0.9800	C18—H18B	0.9700
C24—C19	1.524 (15)	C37—C36	1.524 (15)
C24—C23	1.530 (15)	C37—H37A	0.9700
C24—C25	1.530 (14)	C37—H37B	0.9700
C46—C60	1.504 (14)	C14—H14A	0.9600
C46—C47	1.535 (15)	C14—H14B	0.9600
C25—H25	0.9800	C14—H14C	0.9600
C55—H55	0.9800	C20—C29	1.527 (15)
C12—C11	1.537 (15)	C20—C21	1.527 (15)
C1—C15	1.516 (14)	C20—H20	0.9800
C1—C2	1.526 (15)	C60—H60A	0.9600
C8—C11	1.527 (15)	C60—H60B	0.9600
C8—C7	1.531 (13)	C60—H60C	0.9600
C8—H8	0.9800	C30—H30A	0.9600
C3—C4	1.523 (15)	C30—H30B	0.9600
C3—C2	1.538 (14)	C30—H30C	0.9600
C3—H3A	0.9700	C51—H51A	0.9700
C3—H3B	0.9700	C51—H51B	0.9700
C48—C49	1.530 (15)	C59—H59A	0.9600
C48—C47	1.535 (13)	C59—H59B	0.9600
C48—H48A	0.9700	C59—H59C	0.9600
C48—H48B	0.9700	C35—C36	1.527 (15)
C49—C50	1.538 (14)	C35—C44	1.531 (15)
C49—H49	0.9800	C35—H35	0.9800
C40—C39	1.542 (13)	C58—H58A	0.9600
C40—H40	0.9800	C58—H58B	0.9600
C53—C56	1.540 (15)	C58—H58C	0.9600
C53—C52	1.550 (13)	C2—H2A	0.9700
C53—H53	0.9800	C2—H2B	0.9700
C50—C51	1.530 (15)	C28—H28A	0.9600
C50—C59	1.531 (15)	C28—H28B	0.9600
C50—H50	0.9800	C28—H28C	0.9600
C19—C18	1.520 (15)	C21—H21A	0.9700
C19—C20	1.529 (14)	C21—H21B	0.9700
C19—H19	0.9800	C15—H15A	0.9600
C32—C31	1.525 (15)	C15—H15B	0.9600
C32—C33	1.530 (14)	C15—H15C	0.9600
C32—H32A	0.9700	C44—H44A	0.9600
C32—H32B	0.9700	C44—H44B	0.9600
C4—C5	1.539 (14)	C44—H44C	0.9600
C4—H4	0.9800	C36—H36A	0.9700
C27—C26	1.519 (15)	C36—H36B	0.9700
C5—C14	1.528 (15)	C43—C41	1.524 (15)
C5—C6	1.530 (15)	C43—H43A	0.9600
C5—H5	0.9800	C43—H43B	0.9600
C11—C13	1.521 (15)	C43—H43C	0.9600
C11—H11	0.9800	C29—H29A	0.9600
C17—C18	1.527 (14)	C29—H29B	0.9600
C17—H17A	0.9700	C29—H29C	0.9600
C17—H17B	0.9700	C41—H41	0.9800

C27—O9—C25	126.2 (19)	C8—C7—H7B	109.8
C25—O8—C16	118.5 (18)	H7A—C7—H7B	108.3
C31—O13—O14	110 (2)	O16—C57—O17	120 (3)
C16—O7—O6	113.1 (19)	O16—C57—C56	120 (3)
O19—O20—C54	108.7 (14)	O17—C57—C56	116 (3)
C42—O12—C40	121.0 (18)	C46—C47—C48	118 (3)
O2—O1—C9	110.1 (14)	C46—C47—H47A	107.8
C39—O14—O13	110.1 (16)	C48—C47—H47A	107.8
C40—O15—C31	115.4 (19)	C46—C47—H47B	107.8
C55—O18—C46	116 (2)	C48—C47—H47B	107.8
C1—O2—O1	107 (2)	H47A—C47—H47B	107.1
C46—O19—O20	108 (2)	C39—C38—C37	112 (3)
C24—O6—O7	111.4 (17)	C39—C38—C41	107 (2)
C10—O3—C1	116 (2)	C37—C38—C41	112 (3)
C57—O17—C55	123.6 (19)	C39—C38—H38	108.6
C12—O4—C10	124 (2)	C37—C38—H38	108.6
O7—C16—O8	105.3 (18)	C41—C38—H38	108.6
O7—C16—C30	107 (2)	C27—C26—C28	110 (3)
O8—C16—C30	110 (2)	C27—C26—C23	113 (3)
O7—C16—C17	106 (2)	C28—C26—C23	114 (2)
O8—C16—C17	113 (2)	C27—C26—H26	106.2
C30—C16—C17	114 (2)	C28—C26—H26	106.2
O1—C9—C8	106 (2)	C23—C26—H26	106.2
O1—C9—C4	107 (2)	C58—C56—C57	110 (3)
C8—C9—C4	112.0 (18)	C58—C56—C53	116 (2)
O1—C9—C10	113.1 (17)	C57—C56—C53	112 (3)
C8—C9—C10	109 (2)	C58—C56—H56	106.2
C4—C9—C10	110 (2)	C57—C56—H56	106.2
O20—C54—C53	104 (2)	C53—C56—H56	106.2
O20—C54—C49	107 (2)	C23—C22—C21	111 (3)
C53—C54—C49	110.4 (17)	C23—C22—H22A	109.3
O20—C54—C55	113.9 (16)	C21—C22—H22A	109.3
C53—C54—C55	110 (2)	C23—C22—H22B	109.3
C49—C54—C55	111 (2)	C21—C22—H22B	109.3
O3—C10—O4	105 (2)	H22A—C22—H22B	108.0
O3—C10—C9	111 (2)	C51—C52—C53	106 (3)
O4—C10—C9	110 (2)	C51—C52—H52A	110.4
O3—C10—H10	110.6	C53—C52—H52A	110.4
O4—C10—H10	110.6	C51—C52—H52B	110.4
C9—C10—H10	110.6	C53—C52—H52B	110.4
O6—C24—C19	113 (2)	H52A—C52—H52B	108.6
O6—C24—C23	103 (2)	O11—C42—O12	118 (2)
C19—C24—C23	111.7 (19)	O11—C42—C41	124 (3)
O6—C24—C25	112.3 (17)	O12—C42—C41	117 (3)
C19—C24—C25	109 (2)	C7—C6—C5	114 (2)
C23—C24—C25	109 (3)	C7—C6—H6A	108.7
O19—C46—O18	107.2 (19)	C5—C6—H6A	108.7
O19—C46—C60	108 (3)	C7—C6—H6B	108.7
O18—C46—C60	104 (2)	C5—C6—H6B	108.7
O19—C46—C47	114 (3)	H6A—C6—H6B	107.6
O18—C46—C47	105 (2)	C33—C34—C39	110 (2)
C60—C46—C47	117 (2)	C33—C34—C35	111 (3)
O8—C25—O9	105 (2)	C39—C34—C35	114 (3)
O8—C25—C24	111 (2)	C33—C34—H34	107.1
O9—C25—C24	114 (2)	C39—C34—H34	107.1
O8—C25—H25	108.9	C35—C34—H34	107.1
O9—C25—H25	108.9	C19—C18—C17	121 (3)
C24—C25—H25	108.9	C19—C18—H18A	107.2
O18—C55—O17	109 (2)	C17—C18—H18A	107.2
O18—C55—C54	109 (2)	C19—C18—H18B	107.2
O17—C55—C54	112 (2)	C17—C18—H18B	107.2
O18—C55—H55	109.1	H18A—C18—H18B	106.8
O17—C55—H55	109.1	C36—C37—C38	109 (3)
C54—C55—H55	109.1	C36—C37—H37A	110.0
O5—C12—O4	121 (3)	C38—C37—H37A	110.0
O5—C12—C11	117 (3)	C36—C37—H37B	110.0
O4—C12—C11	116 (3)	C38—C37—H37B	110.0
O2—C1—O3	106 (2)	H37A—C37—H37B	108.3
O2—C1—C15	104 (3)	C5—C14—H14A	109.5
O3—C1—C15	104 (2)	C5—C14—H14B	109.5
O2—C1—C2	114 (3)	H14A—C14—H14B	109.5
O3—C1—C2	110 (2)	C5—C14—H14C	109.5
C15—C1—C2	119 (3)	H14A—C14—H14C	109.5
C9—C8—C11	110 (2)	H14B—C14—H14C	109.5
C9—C8—C7	113 (2)	C29—C20—C21	113 (3)
C11—C8—C7	116 (3)	C29—C20—C19	114 (3)
C9—C8—H8	105.9	C21—C20—C19	109 (3)
C11—C8—H8	105.9	C29—C20—H20	106.9
C7—C8—H8	105.9	C21—C20—H20	106.9
C4—C3—C2	116 (3)	C19—C20—H20	106.9
C4—C3—H3A	108.3	C46—C60—H60A	109.5
C2—C3—H3A	108.3	C46—C60—H60B	109.5
C4—C3—H3B	108.3	H60A—C60—H60B	109.5
C2—C3—H3B	108.3	C46—C60—H60C	109.5
H3A—C3—H3B	107.4	H60A—C60—H60C	109.5
C49—C48—C47	115 (3)	H60B—C60—H60C	109.5
C49—C48—H48A	108.5	C16—C30—H30A	109.5
C47—C48—H48A	108.5	C16—C30—H30B	109.5
C49—C48—H48B	108.5	H30A—C30—H30B	109.5
C47—C48—H48B	108.5	C16—C30—H30C	109.5
H48A—C48—H48B	107.5	H30A—C30—H30C	109.5
C48—C49—C50	114 (3)	H30B—C30—H30C	109.5
C48—C49—C54	112.6 (19)	C52—C51—C50	115 (2)
C50—C49—C54	114 (2)	C52—C51—H51A	108.6
C48—C49—H49	105.1	C50—C51—H51A	108.6
C50—C49—H49	105.1	C52—C51—H51B	108.6
C54—C49—H49	105.1	C50—C51—H51B	108.6
O15—C40—O12	106.7 (19)	H51A—C51—H51B	107.6
O15—C40—C39	109 (2)	C50—C59—H59A	109.5
O12—C40—C39	117 (2)	C50—C59—H59B	109.5
O15—C40—H40	107.7	H59A—C59—H59B	109.5
O12—C40—H40	107.7	C50—C59—H59C	109.5
C39—C40—H40	107.7	H59A—C59—H59C	109.5
C54—C53—C56	109.1 (19)	H59B—C59—H59C	109.5
C54—C53—C52	116 (2)	C36—C35—C44	112 (2)
C56—C53—C52	112 (3)	C36—C35—C34	110 (4)
C54—C53—H53	106.5	C44—C35—C34	112 (3)
C56—C53—H53	106.5	C36—C35—H35	107.7
C52—C53—H53	106.5	C44—C35—H35	107.7
C51—C50—C59	111.1 (18)	C34—C35—H35	107.7
C51—C50—C49	113 (3)	C56—C58—H58A	109.5
C59—C50—C49	111 (3)	C56—C58—H58B	109.5
C51—C50—H50	107.1	H58A—C58—H58B	109.5
C59—C50—H50	107.1	C56—C58—H58C	109.5
C49—C50—H50	107.1	H58A—C58—H58C	109.5
C18—C19—C24	112 (2)	H58B—C58—H58C	109.5
C18—C19—C20	115 (3)	C1—C2—C3	114 (3)
C24—C19—C20	118 (3)	C1—C2—H2A	108.7
C18—C19—H19	103.4	C3—C2—H2A	108.7
C24—C19—H19	103.4	C1—C2—H2B	108.7
C20—C19—H19	103.4	C3—C2—H2B	108.7
C31—C32—C33	116 (3)	H2A—C2—H2B	107.6
C31—C32—H32A	108.4	C26—C28—H28A	109.5
C33—C32—H32A	108.4	C26—C28—H28B	109.5
C31—C32—H32B	108.4	H28A—C28—H28B	109.5
C33—C32—H32B	108.4	C26—C28—H28C	109.5
H32A—C32—H32B	107.4	H28A—C28—H28C	109.5
C3—C4—C9	112 (2)	H28B—C28—H28C	109.5
C3—C4—C5	111 (3)	C20—C21—C22	114 (3)
C9—C4—C5	115 (2)	C20—C21—H21A	108.7
C3—C4—H4	106.0	C22—C21—H21A	108.7
C9—C4—H4	106.0	C20—C21—H21B	108.7
C5—C4—H4	106.0	C22—C21—H21B	108.7
O10—C27—O9	119 (3)	H21A—C21—H21B	107.6
O10—C27—C26	124 (3)	C1—C15—H15A	109.5
O9—C27—C26	116 (3)	C1—C15—H15B	109.5
C14—C5—C6	111 (2)	H15A—C15—H15B	109.5
C14—C5—C4	115 (3)	C1—C15—H15C	109.5
C6—C5—C4	110 (3)	H15A—C15—H15C	109.5
C14—C5—H5	106.9	H15B—C15—H15C	109.5
C6—C5—H5	106.9	C35—C44—H44A	109.5
C4—C5—H5	106.9	C35—C44—H44B	109.5
C13—C11—C8	115 (3)	H44A—C44—H44B	109.5
C13—C11—C12	111 (3)	C35—C44—H44C	109.5
C8—C11—C12	109 (3)	H44A—C44—H44C	109.5
C13—C11—H11	107.2	H44B—C44—H44C	109.5
C8—C11—H11	107.2	C37—C36—C35	115 (2)
C12—C11—H11	107.2	C37—C36—H36A	108.6
C16—C17—C18	115 (3)	C35—C36—H36A	108.6
C16—C17—H17A	108.5	C37—C36—H36B	108.6
C18—C17—H17A	108.5	C35—C36—H36B	108.6
C16—C17—H17B	108.5	H36A—C36—H36B	107.6
C18—C17—H17B	108.5	C41—C43—H43A	109.5
H17A—C17—H17B	107.5	C41—C43—H43B	109.5
C22—C23—C24	111 (3)	H43A—C43—H43B	109.5
C22—C23—C26	115 (3)	C41—C43—H43C	109.5
C24—C23—C26	110 (2)	H43A—C43—H43C	109.5
C22—C23—H23	107.1	H43B—C43—H43C	109.5
C24—C23—H23	107.1	C20—C29—H29A	109.5
C26—C23—H23	107.1	C20—C29—H29B	109.5
C32—C33—C34	119 (3)	H29A—C29—H29B	109.5
C32—C33—H33A	107.5	C20—C29—H29C	109.5
C34—C33—H33A	107.5	H29A—C29—H29C	109.5
C32—C33—H33B	107.5	H29B—C29—H29C	109.5
C34—C33—H33B	107.5	O14—C39—C38	101 (2)
H33A—C33—H33B	107.0	O14—C39—C34	111 (3)
C31—C45—H45A	109.5	C38—C39—C34	110.0 (18)
C31—C45—H45B	109.5	O14—C39—C40	112.6 (15)
H45A—C45—H45B	109.5	C38—C39—C40	109 (2)
C31—C45—H45C	109.5	C34—C39—C40	112 (2)
H45A—C45—H45C	109.5	C42—C41—C43	106 (3)
H45B—C45—H45C	109.5	C42—C41—C38	115 (3)
C11—C13—H13A	109.5	C43—C41—C38	113 (2)
C11—C13—H13B	109.5	C42—C41—H41	107.5
H13A—C13—H13B	109.5	C43—C41—H41	107.5
C11—C13—H13C	109.5	C38—C41—H41	107.5
H13A—C13—H13C	109.5	O13—C31—O15	108.0 (19)
H13B—C13—H13C	109.5	O13—C31—C45	106 (2)
C6—C7—C8	109 (2)	O15—C31—C45	107 (2)
C6—C7—H7A	109.8	O13—C31—C32	115 (2)
C8—C7—H7A	109.8	O15—C31—C32	107 (2)
C6—C7—H7B	109.8	C45—C31—C32	113 (2)

C31—O13—O14—C39	42 (3)	C7—C8—C11—C12	72 (3)
C9—O1—O2—C1	52 (3)	O5—C12—C11—C13	−35 (4)
C54—O20—O19—C46	51 (3)	O4—C12—C11—C13	173 (3)
C16—O7—O6—C24	39 (3)	O5—C12—C11—C8	−162 (3)
O6—O7—C16—O8	−69 (2)	O4—C12—C11—C8	46 (4)
O6—O7—C16—C30	173.4 (19)	O7—C16—C17—C18	−95 (3)
O6—O7—C16—C17	51 (2)	O8—C16—C17—C18	20 (4)
C25—O8—C16—O7	35 (3)	C30—C16—C17—C18	148 (3)
C25—O8—C16—C30	151 (2)	O6—C24—C23—C22	172 (2)
C25—O8—C16—C17	−80 (3)	C19—C24—C23—C22	52 (3)
O2—O1—C9—C8	129 (2)	C25—C24—C23—C22	−68 (3)
O2—O1—C9—C4	−111 (3)	O6—C24—C23—C26	−60 (2)
O2—O1—C9—C10	10 (4)	C19—C24—C23—C26	179.1 (19)
O19—O20—C54—C53	131 (2)	C25—C24—C23—C26	59 (2)
O19—O20—C54—C49	−112 (2)	C31—C32—C33—C34	50 (3)
O19—O20—C54—C55	11 (4)	C9—C8—C7—C6	−56 (3)
C1—O3—C10—O4	−96 (2)	C11—C8—C7—C6	177 (2)
C1—O3—C10—C9	22 (3)	C55—O17—C57—O16	168 (3)
C12—O4—C10—O3	161 (2)	C55—O17—C57—C56	−35 (4)
C12—O4—C10—C9	42 (3)	O19—C46—C47—C48	−91 (3)
O1—C9—C10—O3	−48 (4)	O18—C46—C47—C48	26 (4)
C8—C9—C10—O3	−164.9 (19)	C60—C46—C47—C48	142 (3)
C4—C9—C10—O3	72 (3)	C49—C48—C47—C46	53 (3)
O1—C9—C10—O4	67 (4)	O10—C27—C26—C28	−18 (4)
C8—C9—C10—O4	−50 (2)	O9—C27—C26—C28	160 (2)
C4—C9—C10—O4	−173.1 (17)	O10—C27—C26—C23	−147 (3)
O7—O6—C24—C19	−102 (2)	O9—C27—C26—C23	31 (4)
O7—O6—C24—C23	138 (2)	C22—C23—C26—C27	73 (3)
O7—O6—C24—C25	21 (4)	C24—C23—C26—C27	−52 (3)
O20—O19—C46—O18	−76 (2)	C22—C23—C26—C28	−54 (3)
O20—O19—C46—C60	172 (2)	C24—C23—C26—C28	−179 (2)
O20—O19—C46—C47	40 (2)	O16—C57—C56—C58	−32 (4)
C55—O18—C46—O19	31 (3)	O17—C57—C56—C58	172 (3)
C55—O18—C46—C60	145 (3)	O16—C57—C56—C53	−162 (3)
C55—O18—C46—C47	−91 (3)	O17—C57—C56—C53	42 (4)
C16—O8—C25—O9	−102 (2)	C54—C53—C56—C58	179 (2)
C16—O8—C25—C24	22 (3)	C52—C53—C56—C58	−51 (3)
C27—O9—C25—O8	150 (2)	C54—C53—C56—C57	−54 (3)
C27—O9—C25—C24	28 (3)	C52—C53—C56—C57	76 (3)
O6—C24—C25—O8	−52 (4)	C24—C23—C22—C21	−56 (3)
C19—C24—C25—O8	73 (2)	C26—C23—C22—C21	179 (3)
C23—C24—C25—O8	−165.1 (19)	C54—C53—C52—C51	−57 (3)
O6—C24—C25—O9	66 (3)	C56—C53—C52—C51	177.6 (19)
C19—C24—C25—O9	−168.3 (19)	C40—O12—C42—O11	164 (2)
C23—C24—C25—O9	−47 (2)	C40—O12—C42—C41	−26 (4)
C46—O18—C55—O17	−93 (2)	C8—C7—C6—C5	57 (3)
C46—O18—C55—C54	29 (3)	C14—C5—C6—C7	179.2 (19)
C57—O17—C55—O18	159 (2)	C4—C5—C6—C7	−53 (3)
C57—O17—C55—C54	39 (3)	C32—C33—C34—C39	−32 (3)
O20—C54—C55—O18	−52 (4)	C32—C33—C34—C35	−159 (3)
C53—C54—C55—O18	−168.8 (19)	C24—C19—C18—C17	−23 (4)
C49—C54—C55—O18	69 (2)	C20—C19—C18—C17	−161 (2)
O20—C54—C55—O17	68 (4)	C16—C17—C18—C19	52 (4)
C53—C54—C55—O17	−49 (2)	C39—C38—C37—C36	−58 (3)
C49—C54—C55—O17	−171.2 (19)	C41—C38—C37—C36	−178 (2)
C10—O4—C12—O5	168 (3)	C18—C19—C20—C29	−52 (4)
C10—O4—C12—C11	−41 (4)	C24—C19—C20—C29	173 (3)
O1—O2—C1—O3	−79 (2)	C18—C19—C20—C21	−179 (3)
O1—O2—C1—C15	172 (2)	C24—C19—C20—C21	46 (3)
O1—O2—C1—C2	42 (3)	C53—C52—C51—C50	55 (3)
C10—O3—C1—O2	38 (3)	C59—C50—C51—C52	−179 (2)
C10—O3—C1—C15	147 (3)	C49—C50—C51—C52	−53 (3)
C10—O3—C1—C2	−85 (3)	C33—C34—C35—C36	175 (2)
O1—C9—C8—C11	−61 (2)	C39—C34—C35—C36	50 (3)
C4—C9—C8—C11	−177.2 (17)	C33—C34—C35—C44	−60 (3)
C10—C9—C8—C11	61 (2)	C39—C34—C35—C44	175 (2)
O1—C9—C8—C7	168 (2)	O2—C1—C2—C3	−94 (3)
C4—C9—C8—C7	52 (2)	O3—C1—C2—C3	24 (4)
C10—C9—C8—C7	−70 (3)	C15—C1—C2—C3	143 (3)
C47—C48—C49—C50	−164 (2)	C4—C3—C2—C1	58 (3)
C47—C48—C49—C54	−32 (3)	C29—C20—C21—C22	−178 (2)
O20—C54—C49—C48	69 (2)	C19—C20—C21—C22	−50 (4)
C53—C54—C49—C48	−178.4 (17)	C23—C22—C21—C20	57 (4)
C55—C54—C49—C48	−56 (2)	C38—C37—C36—C35	56 (4)
O20—C54—C49—C50	−160 (3)	C44—C35—C36—C37	−177 (2)
C53—C54—C49—C50	−47 (2)	C34—C35—C36—C37	−52 (4)
C55—C54—C49—C50	76 (3)	O13—O14—C39—C38	136 (2)
C31—O15—C40—O12	−100 (2)	O13—O14—C39—C34	−107 (2)
C31—O15—C40—C39	28 (3)	O13—O14—C39—C40	20 (4)
C42—O12—C40—O15	154 (2)	C37—C38—C39—O14	174 (3)
C42—O12—C40—C39	31 (3)	C41—C38—C39—O14	−63 (2)
O20—C54—C53—C56	−65 (2)	C37—C38—C39—C34	57 (3)
C49—C54—C53—C56	−179.3 (15)	C41—C38—C39—C34	180 (2)
C55—C54—C53—C56	58 (2)	C37—C38—C39—C40	−67 (3)
O20—C54—C53—C52	168 (2)	C41—C38—C39—C40	56 (2)
C49—C54—C53—C52	54 (2)	C33—C34—C39—O14	70 (3)
C55—C54—C53—C52	−69 (2)	C35—C34—C39—O14	−164 (3)
C48—C49—C50—C51	178.3 (18)	C33—C34—C39—C38	−179 (2)
C54—C49—C50—C51	47 (3)	C35—C34—C39—C38	−53 (3)
C48—C49—C50—C59	−56 (3)	C33—C34—C39—C40	−57 (3)
C54—C49—C50—C59	173.0 (18)	C35—C34—C39—C40	69 (3)
O6—C24—C19—C18	60 (3)	O15—C40—C39—O14	−57 (4)
C23—C24—C19—C18	175 (2)	O12—C40—C39—O14	65 (4)
C25—C24—C19—C18	−65 (3)	O15—C40—C39—C38	−167.9 (18)
O6—C24—C19—C20	−164 (3)	O12—C40—C39—C38	−46 (2)
C23—C24—C19—C20	−49 (3)	O15—C40—C39—C34	70 (2)
C25—C24—C19—C20	71 (3)	O12—C40—C39—C34	−169 (2)
C2—C3—C4—C9	−36 (3)	O11—C42—C41—C43	−26 (4)
C2—C3—C4—C5	−167 (2)	O12—C42—C41—C43	164 (3)
O1—C9—C4—C3	68 (3)	O11—C42—C41—C38	−151 (3)
C8—C9—C4—C3	−176.5 (18)	O12—C42—C41—C38	39 (4)
C10—C9—C4—C3	−55 (3)	C39—C38—C41—C42	−54 (3)
O1—C9—C4—C5	−164 (3)	C37—C38—C41—C42	69 (3)
C8—C9—C4—C5	−49 (3)	C39—C38—C41—C43	−176 (2)
C10—C9—C4—C5	73 (3)	C37—C38—C41—C43	−53 (3)
C25—O9—C27—O10	158 (2)	O14—O13—C31—O15	−72 (2)
C25—O9—C27—C26	−19 (4)	O14—O13—C31—C45	173 (2)
C3—C4—C5—C14	−58 (3)	O14—O13—C31—C32	47 (2)
C9—C4—C5—C14	174 (2)	C40—O15—C31—O13	32 (3)
C3—C4—C5—C6	177 (2)	C40—O15—C31—C45	146 (2)
C9—C4—C5—C6	48 (3)	C40—O15—C31—C32	−92 (2)
C9—C8—C11—C13	178 (2)	C33—C32—C31—O13	−89 (3)
C7—C8—C11—C13	−53 (3)	C33—C32—C31—O15	31 (3)
C9—C8—C11—C12	−57 (3)	C33—C32—C31—C45	148 (3)

(FormII_3) top

Crystal data top

C₁₅H₂₂O₅	Z = 4
M_r = 282.32	F(000) = 608
Triclinic, P1	D_x = 1.326 Mg m⁻³
a = 9.7831 (12) Å	Mo Kα radiation, λ = 0.71073 Å
b = 15.150 (2) Å	Cell parameters from 7362 reflections
c = 9.832 (3) Å	θ = 2.1–23.3°
α = 86.565 (19)°	µ = 0.10 mm⁻¹
β = 103.385 (19)°	T = 296 K
γ = 89.287 (8)°	Plate, clear colourless
V = 1414.5 (5) Å³	0.12 × 0.06 × 0.05 mm

Data collection top

Bruker Photon III diffractometer	2713 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	1129 reflections with I > 2σ(I)
Mirror optics monochromator	R_int = 0.073
Detector resolution: 7.9 pixels mm^-1	θ_max = 23.3°, θ_min = 2.1°
ω scans	h = −10→10
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0730 before and 0.0565 after correction. The Ratio of minimum to maximum transmission is 0.8523. The λ/2 correction factor is Not present.	k = −16→16
T_min = 0.635, T_max = 0.745	l = −5→5
7362 measured 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)] = 0.062	w = 1/[σ²(F_o²) + (0.0518P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.138	(Δ/σ)_max < 0.001
S = 0.97	Δρ_max = 0.11 e Å⁻³
2713 reflections	Δρ_min = −0.15 e Å⁻³
321 parameters	Absolute structure: Flack x determined using 372 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
95 restraints	Absolute structure parameter: 1.6 (10)

Special details top

Refinement. CX-ASAP (Thompson, 2023)

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

	x	y	z	U_iso*/U_eq
O9	0.3370 (15)	0.3123 (8)	0.479 (3)	0.054 (5)*
O8	0.3088 (14)	0.3153 (8)	0.241 (3)	0.056 (4)*
O13	0.4799 (16)	0.7249 (8)	0.673 (3)	0.069 (5)*
O7	0.5164 (15)	0.2370 (8)	0.311 (3)	0.071 (5)*
O20	−0.1032 (13)	0.5639 (7)	0.644 (3)	0.052 (4)*
O12	0.6589 (16)	0.8137 (9)	0.501 (4)	0.061 (5)*
O1	1.1050 (14)	0.0739 (7)	0.364 (3)	0.052 (4)*
O14	0.3968 (14)	0.8071 (7)	0.625 (3)	0.064 (4)*
O15	0.6932 (14)	0.7936 (8)	0.742 (3)	0.061 (4)*
O18	0.1873 (13)	0.5122 (8)	0.762 (3)	0.065 (4)*
O2	1.0422 (18)	−0.0113 (9)	0.328 (3)	0.084 (5)*
O19	−0.0430 (16)	0.4743 (8)	0.686 (3)	0.076 (5)*
O6	0.5990 (14)	0.3116 (7)	0.367 (3)	0.070 (4)*
O3	0.8149 (16)	0.0367 (9)	0.249 (3)	0.081 (6)*
O17	0.1558 (16)	0.5316 (9)	0.522 (3)	0.071 (5)*
O11	0.6228 (19)	0.8110 (9)	0.273 (4)	0.103 (7)*
O4	0.8470 (16)	0.0364 (9)	0.483 (3)	0.067 (5)*
O16	0.1101 (18)	0.5300 (10)	0.291 (4)	0.096 (7)*
O10	0.3636 (16)	0.2918 (9)	0.707 (3)	0.082 (5)*
C16	0.414 (2)	0.2669 (12)	0.191 (3)	0.067 (8)*
O5	0.8935 (16)	0.0147 (10)	0.717 (3)	0.088 (6)*
C9	0.9910 (16)	0.1352 (11)	0.373 (3)	0.048 (7)*
C54	0.0142 (16)	0.6233 (10)	0.648 (4)	0.048 (6)*
C10	0.8476 (17)	0.0928 (13)	0.359 (3)	0.059 (7)*
H10	0.774205	0.139152	0.346813	0.071*
C24	0.5155 (17)	0.3904 (10)	0.375 (3)	0.047 (7)*
C46	0.066 (2)	0.4780 (12)	0.808 (3)	0.074 (8)*
C25	0.3617 (17)	0.3644 (14)	0.358 (3)	0.062 (8)*
H25	0.304509	0.419117	0.347086	0.074*
C55	0.1527 (18)	0.5746 (12)	0.648 (3)	0.050 (7)*
H55	0.226557	0.618505	0.661275	0.060*
C12	0.919 (3)	0.0510 (15)	0.613 (3)	0.087 (12)*
C1	0.935 (2)	0.0039 (14)	0.204 (3)	0.097 (10)*
C8	1.0399 (19)	0.1758 (11)	0.514 (3)	0.047 (7)*
H8	1.134286	0.197801	0.516869	0.057*
C3	0.922 (2)	0.1676 (12)	0.109 (3)	0.070 (8)*
H3A	0.949593	0.204864	0.036711	0.084*
H3B	0.819861	0.171060	0.090437	0.084*
C48	0.078 (2)	0.6328 (10)	0.910 (4)	0.068 (8)*
H48A	0.045753	0.664024	0.980747	0.082*
H48B	0.180087	0.633314	0.933853	0.082*
C49	0.025 (2)	0.6831 (11)	0.769 (4)	0.056 (7)*
H49	−0.071748	0.702235	0.766720	0.067*
C40	0.6377 (17)	0.8521 (12)	0.626 (3)	0.053 (7)*
H40	0.694922	0.904934	0.637718	0.063*
C53	−0.0340 (18)	0.6766 (11)	0.508 (4)	0.045 (6)*
H53	−0.128395	0.700270	0.504849	0.054*
C50	0.1061 (19)	0.7686 (11)	0.757 (4)	0.058 (7)*
H50	0.204613	0.750825	0.766438	0.070*
C19	0.526 (3)	0.4562 (12)	0.253 (3)	0.064 (8)*
H19	0.626373	0.463403	0.257999	0.076*
C32	0.537 (2)	0.7949 (11)	0.899 (4)	0.077 (8)*
H32A	0.439067	0.781494	0.891909	0.092*
H32B	0.589216	0.773010	0.990923	0.092*
C4	0.982 (2)	0.2051 (12)	0.251 (3)	0.057 (7)*
H4	1.077906	0.222754	0.251350	0.069*
C27	0.415 (3)	0.3157 (16)	0.611 (3)	0.098 (12)*
C5	0.898 (2)	0.2891 (12)	0.266 (4)	0.067 (8)*
H5	0.799626	0.273067	0.255584	0.080*
C11	1.057 (2)	0.1013 (15)	0.630 (4)	0.060 (8)*
H11	1.129012	0.059648	0.616258	0.071*
C17	0.476 (3)	0.3264 (11)	0.091 (4)	0.091 (9)*
H17A	0.431288	0.314001	−0.004218	0.109*
H17B	0.575255	0.311108	0.106184	0.109*
C23	0.574 (2)	0.4235 (12)	0.520 (3)	0.072 (9)*
H23	0.673966	0.433529	0.528570	0.087*
C33	0.549 (3)	0.8958 (12)	0.888 (5)	0.098 (10)*
H33A	0.507708	0.919932	0.959025	0.117*
H33B	0.647774	0.909656	0.909984	0.117*
C45	0.655 (2)	0.6532 (12)	0.841 (5)	0.090 (8)*
H45A	0.731299	0.658998	0.921405	0.134*
H45B	0.586322	0.615091	0.866486	0.134*
H45C	0.690656	0.628342	0.768062	0.134*
C13	1.104 (3)	0.1326 (14)	0.778 (4)	0.100 (11)*
H13A	1.112018	0.082826	0.844570	0.151*
H13B	1.193194	0.160001	0.787931	0.151*
H13C	1.035723	0.174566	0.793568	0.151*
C7	0.949 (2)	0.2555 (11)	0.531 (4)	0.076 (8)*
H7A	0.854300	0.237265	0.529181	0.092*
H7B	0.987428	0.280430	0.619922	0.092*
C57	0.083 (2)	0.5596 (15)	0.393 (3)	0.085 (11)*
C47	0.032 (2)	0.5361 (10)	0.919 (4)	0.072 (7)*
H47A	0.077454	0.509227	1.010478	0.087*
H47B	−0.068210	0.536027	0.910949	0.087*
C38	0.424 (2)	0.9293 (11)	0.487 (4)	0.063 (7)*
H38	0.323533	0.940663	0.481602	0.075*
C26	0.563 (2)	0.3517 (14)	0.634 (4)	0.061 (8)*
H26	0.623389	0.302255	0.621230	0.073*
C56	−0.049 (2)	0.6159 (13)	0.386 (4)	0.056 (7)*
H56	−0.122098	0.574105	0.397446	0.067*
C22	0.506 (2)	0.5121 (11)	0.537 (4)	0.073 (7)*
H22A	0.550106	0.533587	0.627714	0.088*
H22B	0.406938	0.504598	0.534120	0.088*
C52	0.0584 (19)	0.7566 (10)	0.497 (4)	0.057 (7)*
H52A	0.154132	0.736342	0.502197	0.068*
H52B	0.024082	0.789072	0.406988	0.068*
C42	0.579 (3)	0.8304 (16)	0.372 (4)	0.095 (12)*
C6	0.948 (2)	0.3247 (13)	0.411 (4)	0.066 (8)*
H6A	1.041740	0.346914	0.420099	0.079*
H6B	0.886420	0.373958	0.419221	0.079*
C34	0.480 (2)	0.9426 (13)	0.747 (4)	0.073 (8)*
H34	0.379960	0.951586	0.745488	0.087*
C18	0.461 (3)	0.4258 (13)	0.107 (4)	0.099 (11)*
H18A	0.503581	0.457601	0.039725	0.119*
H18B	0.361316	0.442144	0.083361	0.119*
C37	0.492 (2)	1.0188 (13)	0.470 (5)	0.090 (9)*
H37A	0.590082	1.009125	0.469455	0.108*
H37B	0.445429	1.049076	0.381500	0.108*
C14	0.903 (2)	0.3634 (13)	0.156 (4)	0.085 (8)*
H14A	0.871722	0.341901	0.064009	0.127*
H14B	0.842064	0.411662	0.165861	0.127*
H14C	0.997205	0.383436	0.167614	0.127*
C20	0.466 (2)	0.5476 (11)	0.273 (4)	0.072 (9)*
H20	0.364429	0.541979	0.260370	0.086*
C60	0.108 (2)	0.3826 (11)	0.852 (5)	0.079 (8)*
H60A	0.182048	0.379520	0.934973	0.119*
H60B	0.028070	0.351688	0.869997	0.119*
H60C	0.139307	0.355834	0.777968	0.119*
C30	0.341 (2)	0.1862 (12)	0.129 (4)	0.083 (8)*
H30A	0.270022	0.204140	0.046391	0.124*
H30B	0.408838	0.147559	0.104249	0.124*
H30C	0.298490	0.155728	0.196098	0.124*
C51	0.057 (2)	0.8172 (13)	0.614 (4)	0.063 (7)*
H51A	0.116928	0.866642	0.607008	0.076*
H51B	−0.038246	0.840514	0.604768	0.076*
C59	0.103 (2)	0.8300 (14)	0.874 (4)	0.099 (9)*
H59A	0.134559	0.797944	0.962914	0.148*
H59B	0.163504	0.878583	0.866916	0.148*
H59C	0.008577	0.852097	0.864361	0.148*
C35	0.543 (3)	1.0346 (14)	0.737 (5)	0.108 (10)*
H35	0.643756	1.025567	0.746330	0.129*
C58	−0.098 (2)	0.6593 (12)	0.239 (5)	0.078 (8)*
H58A	−0.181429	0.694913	0.233187	0.117*
H58B	−0.025481	0.696045	0.217841	0.117*
H58C	−0.118391	0.614469	0.172675	0.117*
C2	0.967 (3)	0.0714 (11)	0.095 (4)	0.096 (9)*
H2A	0.919826	0.053951	0.002847	0.115*
H2B	1.066988	0.069422	0.100665	0.115*
C28	0.617 (3)	0.3759 (15)	0.786 (4)	0.112 (13)*
H28A	0.710547	0.398245	0.797236	0.168*
H28B	0.556298	0.420327	0.807104	0.168*
H28C	0.619637	0.324195	0.847658	0.168*
C21	0.523 (3)	0.5794 (16)	0.421 (4)	0.093 (11)*
H21A	0.621328	0.592167	0.432409	0.112*
H21B	0.473194	0.633938	0.429140	0.112*
C15	0.894 (2)	−0.0866 (13)	0.158 (5)	0.105 (10)*
H15A	0.820962	−0.081434	0.074218	0.157*
H15B	0.974262	−0.117314	0.141140	0.157*
H15C	0.860885	−0.119099	0.230756	0.157*
C44	0.525 (3)	1.0910 (16)	0.856 (5)	0.132 (11)*
H44A	0.565623	1.060036	0.944424	0.198*
H44B	0.570580	1.146145	0.849160	0.198*
H44C	0.426355	1.102180	0.849114	0.198*
C36	0.482 (3)	1.0761 (16)	0.590 (5)	0.095 (9)*
H36A	0.383395	1.091372	0.581518	0.114*
H36B	0.529681	1.130770	0.578198	0.114*
C43	0.375 (3)	0.9093 (15)	0.221 (5)	0.107 (10)*
H43A	0.283266	0.934436	0.214429	0.160*
H43B	0.435879	0.954718	0.198964	0.160*
H43C	0.369025	0.864213	0.154925	0.160*
C29	0.489 (3)	0.6186 (16)	0.163 (4)	0.125 (11)*
H29A	0.454162	0.598499	0.070893	0.188*
H29B	0.440636	0.672404	0.172362	0.188*
H29C	0.588132	0.629174	0.176693	0.188*
C39	0.4882 (17)	0.8818 (10)	0.630 (4)	0.055 (7)*
C41	0.435 (2)	0.8687 (15)	0.369 (4)	0.075 (8)*
H41	0.376566	0.817883	0.380331	0.090*
C31	0.589 (2)	0.7432 (11)	0.790 (3)	0.067 (8)*

Geometric parameters (Å, º) top

O9—C27	1.350 (15)	C23—C22	1.525 (14)
O9—C25	1.456 (14)	C23—C26	1.534 (15)
O8—C25	1.409 (15)	C23—H23	0.9800
O8—C16	1.443 (13)	C33—C34	1.522 (15)
O13—C31	1.417 (15)	C33—H33A	0.9700
O13—O14	1.470 (11)	C33—H33B	0.9700
O7—C16	1.410 (15)	C45—C31	1.511 (13)
O7—O6	1.456 (13)	C45—H45A	0.9600
O20—C54	1.463 (13)	C45—H45B	0.9600
O20—O19	1.469 (11)	C45—H45C	0.9600
O12—C42	1.339 (15)	C13—H13A	0.9600
O12—C40	1.444 (15)	C13—H13B	0.9600
O1—C9	1.463 (12)	C13—H13C	0.9600
O1—O2	1.464 (13)	C7—C6	1.525 (15)
O14—C39	1.447 (13)	C7—H7A	0.9700
O15—C40	1.401 (14)	C7—H7B	0.9700
O15—C31	1.430 (13)	C57—C56	1.530 (14)
O18—C55	1.393 (14)	C47—H47A	0.9700
O18—C46	1.456 (13)	C47—H47B	0.9700
O2—C1	1.409 (15)	C38—C39	1.536 (15)
O19—C46	1.414 (15)	C38—C37	1.537 (14)
O6—C24	1.456 (13)	C38—C41	1.544 (15)
O3—C10	1.396 (15)	C38—H38	0.9800
O3—C1	1.443 (14)	C26—C28	1.530 (16)
O17—C57	1.342 (15)	C26—H26	0.9800
O17—C55	1.444 (15)	C56—C58	1.521 (15)
O11—C42	1.199 (15)	C56—H56	0.9800
O4—C12	1.346 (15)	C22—C21	1.528 (15)
O4—C10	1.444 (14)	C22—H22A	0.9700
O16—C57	1.204 (15)	C22—H22B	0.9700
O10—C27	1.206 (15)	C52—C51	1.523 (15)
C16—C30	1.510 (14)	C52—H52A	0.9700
C16—C17	1.528 (15)	C52—H52B	0.9700
O5—C12	1.207 (15)	C42—C41	1.512 (14)
C9—C8	1.527 (15)	C6—H6A	0.9700
C9—C10	1.531 (14)	C6—H6B	0.9700
C9—C4	1.539 (14)	C34—C39	1.529 (15)
C54—C49	1.525 (15)	C34—C35	1.537 (14)
C54—C53	1.526 (15)	C34—H34	0.9800
C54—C55	1.534 (13)	C18—H18A	0.9700
C10—H10	0.9800	C18—H18B	0.9700
C24—C23	1.527 (15)	C37—C36	1.523 (15)
C24—C25	1.534 (14)	C37—H37A	0.9700
C24—C19	1.536 (14)	C37—H37B	0.9700
C46—C60	1.507 (13)	C14—H14A	0.9600
C46—C47	1.530 (15)	C14—H14B	0.9600
C25—H25	0.9800	C14—H14C	0.9600
C55—H55	0.9800	C20—C21	1.535 (15)
C12—C11	1.536 (14)	C20—C29	1.538 (15)
C1—C15	1.500 (14)	C20—H20	0.9800
C1—C2	1.525 (15)	C60—H60A	0.9600
C8—C7	1.529 (13)	C60—H60B	0.9600
C8—C11	1.535 (15)	C60—H60C	0.9600
C8—H8	0.9800	C30—H30A	0.9600
C3—C4	1.530 (15)	C30—H30B	0.9600
C3—C2	1.539 (14)	C30—H30C	0.9600
C3—H3A	0.9700	C51—H51A	0.9700
C3—H3B	0.9700	C51—H51B	0.9700
C48—C49	1.520 (15)	C59—H59A	0.9600
C48—C47	1.540 (13)	C59—H59B	0.9600
C48—H48A	0.9700	C59—H59C	0.9600
C48—H48B	0.9700	C35—C36	1.527 (15)
C49—C50	1.540 (13)	C35—C44	1.530 (15)
C49—H49	0.9800	C35—H35	0.9800
C40—C39	1.535 (13)	C58—H58A	0.9600
C40—H40	0.9800	C58—H58B	0.9600
C53—C56	1.533 (15)	C58—H58C	0.9600
C53—C52	1.535 (13)	C2—H2A	0.9700
C53—H53	0.9800	C2—H2B	0.9700
C50—C51	1.517 (15)	C28—H28A	0.9600
C50—C59	1.523 (15)	C28—H28B	0.9600
C50—H50	0.9800	C28—H28C	0.9600
C19—C18	1.532 (15)	C21—H21A	0.9700
C19—C20	1.537 (14)	C21—H21B	0.9700
C19—H19	0.9800	C15—H15A	0.9600
C32—C33	1.533 (13)	C15—H15B	0.9600
C32—C31	1.534 (15)	C15—H15C	0.9600
C32—H32A	0.9700	C44—H44A	0.9600
C32—H32B	0.9700	C44—H44B	0.9600
C4—C5	1.539 (14)	C44—H44C	0.9600
C4—H4	0.9800	C36—H36A	0.9700
C27—C26	1.528 (14)	C36—H36B	0.9700
C5—C14	1.525 (15)	C43—C41	1.530 (15)
C5—C6	1.528 (15)	C43—H43A	0.9600
C5—H5	0.9800	C43—H43B	0.9600
C11—C13	1.526 (15)	C43—H43C	0.9600
C11—H11	0.9800	C29—H29A	0.9600
C17—C18	1.533 (14)	C29—H29B	0.9600
C17—H17A	0.9700	C29—H29C	0.9600
C17—H17B	0.9700	C41—H41	0.9800

C27—O9—C25	124.6 (17)	C8—C7—H7B	109.9
C25—O8—C16	115.1 (17)	H7A—C7—H7B	108.3
C31—O13—O14	107.9 (17)	O16—C57—O17	121 (2)
C16—O7—O6	109.2 (16)	O16—C57—C56	123 (3)
C54—O20—O19	107.3 (12)	O17—C57—C56	116 (3)
C42—O12—C40	125.6 (15)	C46—C47—C48	116 (2)
C9—O1—O2	107.4 (13)	C46—C47—H47A	108.4
C39—O14—O13	110.3 (14)	C48—C47—H47A	108.4
C40—O15—C31	113.4 (16)	C46—C47—H47B	108.4
C55—O18—C46	113.7 (15)	C48—C47—H47B	108.4
C1—O2—O1	107.7 (18)	H47A—C47—H47B	107.4
C46—O19—O20	108.6 (18)	C39—C38—C37	111 (2)
C24—O6—O7	114.2 (14)	C39—C38—C41	109.9 (17)
C10—O3—C1	114.3 (19)	C37—C38—C41	112 (3)
C57—O17—C55	124.8 (15)	C39—C38—H38	107.9
C12—O4—C10	124.9 (17)	C37—C38—H38	107.9
O7—C16—O8	106.2 (16)	C41—C38—H38	107.9
O7—C16—C30	107.1 (19)	C27—C26—C28	111 (2)
O8—C16—C30	105.7 (17)	C27—C26—C23	112 (2)
O7—C16—C17	112 (2)	C28—C26—C23	116 (2)
O8—C16—C17	110.4 (17)	C27—C26—H26	105.8
C30—C16—C17	115.3 (19)	C28—C26—H26	105.8
O1—C9—C8	105.1 (18)	C23—C26—H26	105.8
O1—C9—C10	114.6 (15)	C58—C56—C57	109 (2)
C8—C9—C10	112 (2)	C58—C56—C53	116.9 (17)
O1—C9—C4	105.4 (16)	C57—C56—C53	113 (2)
C8—C9—C4	111.1 (17)	C58—C56—H56	105.8
C10—C9—C4	108.9 (18)	C57—C56—H56	105.8
O20—C54—C49	109 (2)	C53—C56—H56	105.8
O20—C54—C53	101.3 (19)	C23—C22—C21	110 (2)
C49—C54—C53	110.6 (14)	C23—C22—H22A	109.7
O20—C54—C55	113.2 (13)	C21—C22—H22A	109.7
C49—C54—C55	114 (2)	C23—C22—H22B	109.7
C53—C54—C55	108 (2)	C21—C22—H22B	109.7
O3—C10—O4	104.4 (18)	H22A—C22—H22B	108.2
O3—C10—C9	113.3 (18)	C51—C52—C53	110 (2)
O4—C10—C9	110.1 (17)	C51—C52—H52A	109.6
O3—C10—H10	109.6	C53—C52—H52A	109.6
O4—C10—H10	109.6	C51—C52—H52B	109.6
C9—C10—H10	109.6	C53—C52—H52B	109.6
O6—C24—C23	106.1 (19)	H52A—C52—H52B	108.1
O6—C24—C25	108.5 (15)	O11—C42—O12	120 (2)
C23—C24—C25	111 (2)	O11—C42—C41	127 (3)
O6—C24—C19	108.0 (17)	O12—C42—C41	113 (3)
C23—C24—C19	114.6 (18)	C7—C6—C5	113 (2)
C25—C24—C19	108.8 (19)	C7—C6—H6A	108.9
O19—C46—O18	106.2 (18)	C5—C6—H6A	108.9
O19—C46—C60	104 (2)	C7—C6—H6B	108.9
O18—C46—C60	103.2 (15)	C5—C6—H6B	108.9
O19—C46—C47	114.9 (19)	H6A—C6—H6B	107.7
O18—C46—C47	109.4 (18)	C33—C34—C39	109.1 (19)
C60—C46—C47	118 (2)	C33—C34—C35	109 (3)
O8—C25—O9	106.2 (18)	C39—C34—C35	116 (2)
O8—C25—C24	114.5 (18)	C33—C34—H34	107.2
O9—C25—C24	113.0 (17)	C39—C34—H34	107.2
O8—C25—H25	107.6	C35—C34—H34	107.2
O9—C25—H25	107.6	C19—C18—C17	115 (2)
C24—C25—H25	107.6	C19—C18—H18A	108.5
O18—C55—O17	108.7 (17)	C17—C18—H18A	108.5
O18—C55—C54	110.3 (19)	C19—C18—H18B	108.5
O17—C55—C54	115 (2)	C17—C18—H18B	108.5
O18—C55—H55	107.3	H18A—C18—H18B	107.5
O17—C55—H55	107.3	C36—C37—C38	111 (3)
C54—C55—H55	107.3	C36—C37—H37A	109.5
O5—C12—O4	123 (2)	C38—C37—H37A	109.5
O5—C12—C11	118 (2)	C36—C37—H37B	109.5
O4—C12—C11	118 (2)	C38—C37—H37B	109.5
O2—C1—O3	105.7 (18)	H37A—C37—H37B	108.1
O2—C1—C15	105 (2)	C5—C14—H14A	109.5
O3—C1—C15	103.9 (18)	C5—C14—H14B	109.5
O2—C1—C2	116 (2)	H14A—C14—H14B	109.5
O3—C1—C2	108 (2)	C5—C14—H14C	109.5
C15—C1—C2	118 (2)	H14A—C14—H14C	109.5
C9—C8—C7	113.3 (19)	H14B—C14—H14C	109.5
C9—C8—C11	108 (2)	C21—C20—C19	113 (2)
C7—C8—C11	115.4 (19)	C21—C20—C29	110 (2)
C9—C8—H8	106.5	C19—C20—C29	112 (2)
C7—C8—H8	106.5	C21—C20—H20	107.0
C11—C8—H8	106.5	C19—C20—H20	107.0
C4—C3—C2	116 (2)	C29—C20—H20	107.0
C4—C3—H3A	108.4	C46—C60—H60A	109.5
C2—C3—H3A	108.4	C46—C60—H60B	109.5
C4—C3—H3B	108.4	H60A—C60—H60B	109.5
C2—C3—H3B	108.4	C46—C60—H60C	109.5
H3A—C3—H3B	107.5	H60A—C60—H60C	109.5
C49—C48—C47	115 (2)	H60B—C60—H60C	109.5
C49—C48—H48A	108.4	C16—C30—H30A	109.5
C47—C48—H48A	108.4	C16—C30—H30B	109.5
C49—C48—H48B	108.4	H30A—C30—H30B	109.5
C47—C48—H48B	108.4	C16—C30—H30C	109.5
H48A—C48—H48B	107.5	H30A—C30—H30C	109.5
C48—C49—C54	112.0 (16)	H30B—C30—H30C	109.5
C48—C49—C50	112 (2)	C50—C51—C52	111.5 (17)
C54—C49—C50	115 (2)	C50—C51—H51A	109.3
C48—C49—H49	105.8	C52—C51—H51A	109.3
C54—C49—H49	105.8	C50—C51—H51B	109.3
C50—C49—H49	105.8	C52—C51—H51B	109.3
O15—C40—O12	108.8 (17)	H51A—C51—H51B	108.0
O15—C40—C39	109.5 (19)	C50—C59—H59A	109.5
O12—C40—C39	118 (2)	C50—C59—H59B	109.5
O15—C40—H40	106.5	H59A—C59—H59B	109.5
O12—C40—H40	106.5	C50—C59—H59C	109.5
C39—C40—H40	106.5	H59A—C59—H59C	109.5
C54—C53—C56	110.5 (16)	H59B—C59—H59C	109.5
C54—C53—C52	112 (2)	C36—C35—C44	115 (2)
C56—C53—C52	114 (2)	C36—C35—C34	108 (3)
C54—C53—H53	106.5	C44—C35—C34	112 (3)
C56—C53—H53	106.5	C36—C35—H35	107.1
C52—C53—H53	106.5	C44—C35—H35	107.1
C51—C50—C59	110.8 (16)	C34—C35—H35	107.1
C51—C50—C49	112 (2)	C56—C58—H58A	109.5
C59—C50—C49	113 (2)	C56—C58—H58B	109.5
C51—C50—H50	106.9	H58A—C58—H58B	109.5
C59—C50—H50	106.9	C56—C58—H58C	109.5
C49—C50—H50	106.9	H58A—C58—H58C	109.5
C18—C19—C24	115 (2)	H58B—C58—H58C	109.5
C18—C19—C20	111 (2)	C1—C2—C3	115 (2)
C24—C19—C20	110.4 (18)	C1—C2—H2A	108.4
C18—C19—H19	106.6	C3—C2—H2A	108.4
C24—C19—H19	106.6	C1—C2—H2B	108.4
C20—C19—H19	106.6	C3—C2—H2B	108.4
C33—C32—C31	117 (2)	H2A—C2—H2B	107.5
C33—C32—H32A	108.0	C26—C28—H28A	109.5
C31—C32—H32A	108.0	C26—C28—H28B	109.5
C33—C32—H32B	108.0	H28A—C28—H28B	109.5
C31—C32—H32B	108.0	C26—C28—H28C	109.5
H32A—C32—H32B	107.3	H28A—C28—H28C	109.5
C3—C4—C9	112.0 (19)	H28B—C28—H28C	109.5
C3—C4—C5	110 (2)	C22—C21—C20	113 (2)
C9—C4—C5	112.9 (17)	C22—C21—H21A	108.9
C3—C4—H4	107.1	C20—C21—H21A	108.9
C9—C4—H4	107.1	C22—C21—H21B	108.9
C5—C4—H4	107.1	C20—C21—H21B	108.9
O10—C27—O9	119 (2)	H21A—C21—H21B	107.7
O10—C27—C26	122 (2)	C1—C15—H15A	109.5
O9—C27—C26	119 (2)	C1—C15—H15B	109.5
C14—C5—C6	109 (2)	H15A—C15—H15B	109.5
C14—C5—C4	113.6 (19)	C1—C15—H15C	109.5
C6—C5—C4	112 (2)	H15A—C15—H15C	109.5
C14—C5—H5	107.5	H15B—C15—H15C	109.5
C6—C5—H5	107.5	C35—C44—H44A	109.5
C4—C5—H5	107.5	C35—C44—H44B	109.5
C13—C11—C8	114 (2)	H44A—C44—H44B	109.5
C13—C11—C12	111 (2)	C35—C44—H44C	109.5
C8—C11—C12	110 (2)	H44A—C44—H44C	109.5
C13—C11—H11	107.4	H44B—C44—H44C	109.5
C8—C11—H11	107.4	C37—C36—C35	116 (2)
C12—C11—H11	107.4	C37—C36—H36A	108.4
C16—C17—C18	115 (2)	C35—C36—H36A	108.4
C16—C17—H17A	108.5	C37—C36—H36B	108.4
C18—C17—H17A	108.5	C35—C36—H36B	108.4
C16—C17—H17B	108.5	H36A—C36—H36B	107.4
C18—C17—H17B	108.5	C41—C43—H43A	109.5
H17A—C17—H17B	107.5	C41—C43—H43B	109.5
C22—C23—C24	112 (2)	H43A—C43—H43B	109.5
C22—C23—C26	113.8 (19)	C41—C43—H43C	109.5
C24—C23—C26	110 (2)	H43A—C43—H43C	109.5
C22—C23—H23	107.0	H43B—C43—H43C	109.5
C24—C23—H23	107.0	C20—C29—H29A	109.5
C26—C23—H23	107.0	C20—C29—H29B	109.5
C34—C33—C32	116 (3)	H29A—C29—H29B	109.5
C34—C33—H33A	108.3	C20—C29—H29C	109.5
C32—C33—H33A	108.3	H29A—C29—H29C	109.5
C34—C33—H33B	108.3	H29B—C29—H29C	109.5
C32—C33—H33B	108.3	O14—C39—C34	114 (2)
H33A—C33—H33B	107.4	O14—C39—C40	111.0 (13)
C31—C45—H45A	109.5	C34—C39—C40	115 (2)
C31—C45—H45B	109.5	O14—C39—C38	100 (2)
H45A—C45—H45B	109.5	C34—C39—C38	109.9 (16)
C31—C45—H45C	109.5	C40—C39—C38	106 (2)
H45A—C45—H45C	109.5	C42—C41—C43	107 (2)
H45B—C45—H45C	109.5	C42—C41—C38	117 (3)
C11—C13—H13A	109.5	C43—C41—C38	114.8 (19)
C11—C13—H13B	109.5	C42—C41—H41	105.8
H13A—C13—H13B	109.5	C43—C41—H41	105.8
C11—C13—H13C	109.5	C38—C41—H41	105.8
H13A—C13—H13C	109.5	O13—C31—O15	109.1 (19)
H13B—C13—H13C	109.5	O13—C31—C45	103 (2)
C6—C7—C8	108.9 (18)	O15—C31—C45	106.4 (16)
C6—C7—H7A	109.9	O13—C31—C32	113.3 (19)
C8—C7—H7A	109.9	O15—C31—C32	108.5 (18)
C6—C7—H7B	109.9	C45—C31—C32	116 (2)

C31—O13—O14—C39	41 (3)	C7—C8—C11—C12	73 (3)
C9—O1—O2—C1	54 (2)	O5—C12—C11—C13	−26 (3)
C54—O20—O19—C46	47 (3)	O4—C12—C11—C13	165 (2)
C16—O7—O6—C24	46 (2)	O5—C12—C11—C8	−153 (2)
O6—O7—C16—O8	−73.2 (19)	O4—C12—C11—C8	39 (3)
O6—O7—C16—C30	174.2 (14)	O7—C16—C17—C18	−96 (3)
O6—O7—C16—C17	47 (2)	O8—C16—C17—C18	22 (3)
C25—O8—C16—O7	36 (2)	C30—C16—C17—C18	142 (2)
C25—O8—C16—C30	149.6 (18)	O6—C24—C23—C22	173.7 (15)
C25—O8—C16—C17	−85 (2)	C25—C24—C23—C22	−69 (2)
O2—O1—C9—C8	129.5 (19)	C19—C24—C23—C22	55 (2)
O2—O1—C9—C10	7 (3)	O6—C24—C23—C26	−59 (2)
O2—O1—C9—C4	−113 (2)	C25—C24—C23—C26	58.7 (19)
O19—O20—C54—C49	−110 (2)	C19—C24—C23—C26	−177.9 (15)
O19—O20—C54—C53	133 (2)	C31—C32—C33—C34	55 (3)
O19—O20—C54—C55	17 (4)	C9—C8—C7—C6	−57 (2)
C1—O3—C10—O4	−98.2 (19)	C11—C8—C7—C6	178 (2)
C1—O3—C10—C9	22 (3)	C55—O17—C57—O16	167 (2)
C12—O4—C10—O3	155 (2)	C55—O17—C57—C56	−25 (3)
C12—O4—C10—C9	33 (3)	O19—C46—C47—C48	−93 (2)
O1—C9—C10—O3	−46 (3)	O18—C46—C47—C48	27 (3)
C8—C9—C10—O3	−165.1 (15)	C60—C46—C47—C48	144 (2)
C4—C9—C10—O3	72 (2)	C49—C48—C47—C46	54 (2)
O1—C9—C10—O4	71 (3)	O10—C27—C26—C28	−15 (3)
C8—C9—C10—O4	−49 (2)	O9—C27—C26—C28	163 (2)
C4—C9—C10—O4	−171.7 (16)	O10—C27—C26—C23	−146 (3)
O7—O6—C24—C23	133.5 (18)	O9—C27—C26—C23	32 (3)
O7—O6—C24—C25	15 (3)	C22—C23—C26—C27	75 (3)
O7—O6—C24—C19	−103 (2)	C24—C23—C26—C27	−51 (3)
O20—O19—C46—O18	−78.3 (18)	C22—C23—C26—C28	−54 (3)
O20—O19—C46—C60	173.0 (16)	C24—C23—C26—C28	−179.9 (19)
O20—O19—C46—C47	42.9 (19)	O16—C57—C56—C58	−25 (3)
C55—O18—C46—O19	35 (2)	O17—C57—C56—C58	167 (2)
C55—O18—C46—C60	144 (2)	O16—C57—C56—C53	−156 (2)
C55—O18—C46—C47	−90 (2)	O17—C57—C56—C53	35 (3)
C16—O8—C25—O9	−100.9 (16)	C54—C53—C56—C58	179.4 (16)
C16—O8—C25—C24	24 (2)	C52—C53—C56—C58	−53 (2)
C27—O9—C25—O8	153 (2)	C54—C53—C56—C57	−53 (2)
C27—O9—C25—C24	27 (3)	C52—C53—C56—C57	74 (2)
O6—C24—C25—O8	−51 (3)	C24—C23—C22—C21	−55 (3)
C23—C24—C25—O8	−166.6 (16)	C26—C23—C22—C21	180 (2)
C19—C24—C25—O8	67 (2)	C54—C53—C52—C51	−59 (2)
O6—C24—C25—O9	71 (3)	C56—C53—C52—C51	174.8 (15)
C23—C24—C25—O9	−45 (2)	C40—O12—C42—O11	163.4 (19)
C19—C24—C25—O9	−171.6 (18)	C40—O12—C42—C41	−20 (4)
C46—O18—C55—O17	−100 (2)	C8—C7—C6—C5	56 (3)
C46—O18—C55—C54	28 (3)	C14—C5—C6—C7	−179.3 (14)
C57—O17—C55—O18	155.0 (19)	C4—C5—C6—C7	−53 (2)
C57—O17—C55—C54	30 (3)	C32—C33—C34—C39	−32 (3)
O20—C54—C55—O18	−57 (4)	C32—C33—C34—C35	−161 (2)
C49—C54—C55—O18	68 (2)	C24—C19—C18—C17	−35 (3)
C53—C54—C55—O18	−168.7 (17)	C20—C19—C18—C17	−161.7 (17)
O20—C54—C55—O17	66 (3)	C16—C17—C18—C19	58 (3)
C49—C54—C55—O17	−168.0 (16)	C39—C38—C37—C36	−56 (2)
C53—C54—C55—O17	−45 (2)	C41—C38—C37—C36	−178.8 (19)
C10—O4—C12—O5	163 (2)	C18—C19—C20—C21	177 (2)
C10—O4—C12—C11	−29 (3)	C24—C19—C20—C21	48 (3)
O1—O2—C1—O3	−80.6 (19)	C18—C19—C20—C29	−58 (3)
O1—O2—C1—C15	169.9 (17)	C24—C19—C20—C29	173 (2)
O1—O2—C1—C2	39 (2)	C59—C50—C51—C52	−179.7 (16)
C10—O3—C1—O2	37 (2)	C49—C50—C51—C52	−52 (2)
C10—O3—C1—C15	147 (2)	C53—C52—C51—C50	58 (2)
C10—O3—C1—C2	−87 (2)	C33—C34—C35—C36	174.6 (19)
O1—C9—C8—C7	168.3 (14)	C39—C34—C35—C36	51 (3)
C10—C9—C8—C7	−67 (2)	C33—C34—C35—C44	−58 (3)
C4—C9—C8—C7	54.8 (19)	C39—C34—C35—C44	178 (2)
O1—C9—C8—C11	−62.6 (17)	O2—C1—C2—C3	−90 (3)
C10—C9—C8—C11	62.2 (17)	O3—C1—C2—C3	28 (3)
C4—C9—C8—C11	−176.1 (13)	C15—C1—C2—C3	145 (2)
C47—C48—C49—C54	−34 (2)	C4—C3—C2—C1	56 (3)
C47—C48—C49—C50	−164 (2)	C23—C22—C21—C20	55 (3)
O20—C54—C49—C48	71 (2)	C19—C20—C21—C22	−52 (3)
C53—C54—C49—C48	−177.8 (13)	C29—C20—C21—C22	−179.1 (17)
C55—C54—C49—C48	−56 (2)	C38—C37—C36—C35	55 (3)
O20—C54—C49—C50	−160 (2)	C44—C35—C36—C37	−177 (2)
C53—C54—C49—C50	−49 (2)	C34—C35—C36—C37	−51 (3)
C55—C54—C49—C50	73 (2)	O13—O14—C39—C34	−109 (2)
C31—O15—C40—O12	−101 (2)	O13—O14—C39—C40	23 (4)
C31—O15—C40—C39	30 (3)	O13—O14—C39—C38	135 (2)
C42—O12—C40—O15	153 (2)	C33—C34—C39—O14	71 (2)
C42—O12—C40—C39	27 (3)	C35—C34—C39—O14	−165 (3)
O20—C54—C53—C56	−62.2 (18)	C33—C34—C39—C40	−58 (2)
C49—C54—C53—C56	−178.2 (14)	C35—C34—C39—C40	66 (3)
C55—C54—C53—C56	57.0 (19)	C33—C34—C39—C38	−178.0 (16)
O20—C54—C53—C52	169 (2)	C35—C34—C39—C38	−54 (2)
C49—C54—C53—C52	53.3 (19)	O15—C40—C39—O14	−61 (3)
C55—C54—C53—C52	−72 (2)	O12—C40—C39—O14	65 (3)
C48—C49—C50—C51	177.9 (16)	O15—C40—C39—C34	70 (2)
C54—C49—C50—C51	49 (2)	O12—C40—C39—C34	−164.8 (18)
C48—C49—C50—C59	−56 (2)	O15—C40—C39—C38	−168.5 (17)
C54—C49—C50—C59	174.8 (16)	O12—C40—C39—C38	−43 (2)
O6—C24—C19—C18	65 (3)	C37—C38—C39—O14	174 (2)
C23—C24—C19—C18	−177 (2)	C41—C38—C39—O14	−61.6 (19)
C25—C24—C19—C18	−52 (2)	C37—C38—C39—C34	54 (2)
O6—C24—C19—C20	−168 (2)	C41—C38—C39—C34	178.8 (17)
C23—C24—C19—C20	−50 (2)	C37—C38—C39—C40	−71 (2)
C25—C24—C19—C20	74 (2)	C41—C38—C39—C40	54 (2)
C2—C3—C4—C9	−37 (2)	O11—C42—C41—C43	−20 (3)
C2—C3—C4—C5	−163.7 (17)	O12—C42—C41—C43	163 (2)
O1—C9—C4—C3	71 (2)	O11—C42—C41—C38	−150 (3)
C8—C9—C4—C3	−175.4 (16)	O12—C42—C41—C38	33 (3)
C10—C9—C4—C3	−52 (2)	C39—C38—C41—C42	−53 (3)
O1—C9—C4—C5	−164 (2)	C37—C38—C41—C42	71 (3)
C8—C9—C4—C5	−50 (2)	C39—C38—C41—C43	−179.3 (18)
C10—C9—C4—C5	73 (3)	C37—C38—C41—C43	−55 (3)
C25—O9—C27—O10	158 (2)	O14—O13—C31—O15	−73.9 (18)
C25—O9—C27—C26	−21 (4)	O14—O13—C31—C45	173.3 (17)
C3—C4—C5—C14	−61 (3)	O14—O13—C31—C32	47.1 (18)
C9—C4—C5—C14	173 (2)	C40—O15—C31—O13	34 (2)
C3—C4—C5—C6	175.6 (18)	C40—O15—C31—C45	145 (2)
C9—C4—C5—C6	50 (3)	C40—O15—C31—C32	−90 (2)
C9—C8—C11—C13	−179.4 (18)	C33—C32—C31—O13	−95 (2)
C7—C8—C11—C13	−51 (3)	C33—C32—C31—O15	26 (3)
C9—C8—C11—C12	−55 (2)	C33—C32—C31—C45	146 (2)

(FormII_4) top

Crystal data top

C₁₅H₂₂O₅	Z = 4
M_r = 282.32	F(000) = 608
Triclinic, P1	D_x = 1.387 Mg m⁻³
a = 9.637 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.741 (4) Å	Cell parameters from 5569 reflections
c = 9.796 (5) Å	θ = 2.2–23.2°
α = 88.93 (3)°	µ = 0.10 mm⁻¹
β = 103.73 (3)°	T = 296 K
γ = 89.846 (14)°	Plate, clear colourless
V = 1351.6 (9) Å³	0.12 × 0.06 × 0.05 mm

Data collection top

Bruker Photon III diffractometer	2459 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	1088 reflections with I > 2σ(I)
Mirror optics monochromator	R_int = 0.070
Detector resolution: 7.9 pixels mm^-1	θ_max = 23.2°, θ_min = 2.2°
ω scans	h = −10→10
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0750 before and 0.0570 after correction. The Ratio of minimum to maximum transmission is 0.8504. The λ/2 correction factor is Not present.	k = −16→16
T_min = 0.649, T_max = 0.745	l = −5→5
5569 measured 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)] = 0.075	w = 1/[σ²(F_o²) + (0.1003P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.209	(Δ/σ)_max < 0.001
S = 0.98	Δρ_max = 0.14 e Å⁻³
2459 reflections	Δρ_min = −0.17 e Å⁻³
321 parameters	Absolute structure: Flack x determined using 344 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
95 restraints	Absolute structure parameter: −0.5 (10)

Special details top

Refinement. CX-ASAP (Thompson, 2023)

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

	x	y	z	U_iso*/U_eq
O9	0.3329 (19)	0.3118 (11)	0.469 (3)	0.056 (6)*
O8	0.3037 (19)	0.3107 (11)	0.234 (4)	0.049 (5)*
O13	0.482 (2)	0.7315 (12)	0.685 (4)	0.075 (7)*
O7	0.519 (2)	0.2341 (11)	0.318 (4)	0.071 (6)*
O20	−0.1098 (17)	0.5625 (10)	0.650 (4)	0.048 (5)*
O12	0.6622 (19)	0.8123 (11)	0.518 (4)	0.059 (6)*
O1	1.1122 (18)	0.0668 (10)	0.362 (4)	0.049 (5)*
O14	0.3959 (17)	0.8144 (9)	0.637 (4)	0.052 (5)*
O15	0.6961 (18)	0.8044 (11)	0.758 (4)	0.054 (5)*
O18	0.1820 (18)	0.5106 (11)	0.764 (4)	0.059 (6)*
O2	1.055 (2)	−0.0229 (11)	0.316 (4)	0.075 (7)*
O19	−0.049 (2)	0.4724 (11)	0.692 (4)	0.068 (6)*
O6	0.6041 (18)	0.3149 (9)	0.367 (4)	0.062 (6)*
O3	0.8177 (18)	0.0181 (12)	0.234 (4)	0.063 (6)*
O17	0.1508 (17)	0.5215 (11)	0.530 (4)	0.050 (5)*
O11	0.637 (2)	0.8072 (11)	0.289 (5)	0.077 (7)*
O4	0.851 (2)	0.0245 (12)	0.476 (4)	0.062 (7)*
O16	0.109 (2)	0.5203 (12)	0.298 (4)	0.067 (6)*
O10	0.3613 (19)	0.3018 (11)	0.699 (4)	0.060 (6)*
C16	0.415 (3)	0.2592 (17)	0.195 (3)	0.078 (11)*
O5	0.893 (2)	0.0150 (12)	0.710 (4)	0.075 (6)*
C9	0.9922 (18)	0.1277 (13)	0.364 (4)	0.049 (8)*
C54	0.009 (2)	0.6247 (12)	0.647 (5)	0.035 (7)*
C10	0.851 (2)	0.0771 (16)	0.349 (3)	0.036 (7)*
H10	0.774327	0.122447	0.336115	0.044*
C24	0.514 (2)	0.3939 (13)	0.370 (4)	0.043 (9)*
C46	0.062 (3)	0.4787 (16)	0.814 (4)	0.063 (10)*
C25	0.358 (2)	0.3653 (18)	0.351 (3)	0.045 (8)*
H25	0.298562	0.420368	0.340743	0.054*
C55	0.150 (2)	0.5739 (16)	0.652 (4)	0.052 (9)*
H55	0.227650	0.618141	0.664960	0.062*
C12	0.925 (3)	0.0449 (18)	0.606 (4)	0.069 (12)*
C1	0.944 (3)	−0.0130 (16)	0.193 (4)	0.064 (10)*
C8	1.041 (3)	0.1736 (14)	0.505 (4)	0.041 (8)*
H8	1.136657	0.198091	0.508698	0.050*
C3	0.928 (3)	0.1522 (15)	0.099 (4)	0.069 (11)*
H3A	0.960728	0.189390	0.030072	0.082*
H3B	0.824119	0.154655	0.073358	0.082*
C48	0.077 (3)	0.6385 (14)	0.913 (6)	0.065 (9)*
H48A	0.045516	0.673257	0.983170	0.077*
H48B	0.180531	0.640664	0.935781	0.077*
C49	0.024 (3)	0.6879 (14)	0.772 (6)	0.046 (8)*
H49	−0.073144	0.709637	0.769798	0.055*
C40	0.644 (2)	0.8604 (17)	0.639 (4)	0.051 (9)*
H40	0.703085	0.914891	0.648401	0.061*
C53	−0.041 (2)	0.6734 (13)	0.505 (5)	0.031 (7)*
H53	−0.136716	0.698137	0.501144	0.037*
C50	0.113 (2)	0.7728 (14)	0.759 (5)	0.041 (7)*
H50	0.212072	0.753742	0.767848	0.049*
C19	0.520 (3)	0.4579 (17)	0.247 (4)	0.061 (10)*
H19	0.621823	0.467673	0.254482	0.073*
C32	0.535 (3)	0.8102 (14)	0.913 (5)	0.082 (11)*
H32A	0.436405	0.794943	0.908111	0.098*
H32B	0.589849	0.793560	1.007087	0.098*
C4	0.978 (3)	0.1960 (15)	0.241 (4)	0.042 (8)*
H4	1.075434	0.216804	0.245219	0.050*
C27	0.406 (3)	0.329 (2)	0.601 (4)	0.077 (13)*
C5	0.892 (3)	0.2818 (14)	0.256 (5)	0.040 (8)*
H5	0.793431	0.262344	0.249022	0.048*
C11	1.059 (2)	0.1026 (18)	0.625 (4)	0.045 (9)*
H11	1.134859	0.061362	0.612977	0.054*
C17	0.475 (3)	0.3178 (15)	0.091 (5)	0.073 (10)*
H17A	0.574847	0.302058	0.102757	0.088*
H17B	0.426047	0.300674	−0.003764	0.088*
C23	0.572 (3)	0.4301 (14)	0.518 (4)	0.054 (10)*
H23	0.674283	0.439823	0.527486	0.065*
C33	0.545 (3)	0.9134 (14)	0.894 (6)	0.063 (9)*
H33A	0.501226	0.942119	0.961231	0.076*
H33B	0.645396	0.929513	0.917174	0.076*
C45	0.662 (3)	0.6638 (15)	0.861 (6)	0.064 (9)*
H45A	0.735727	0.674313	0.943970	0.096*
H45B	0.593079	0.622594	0.883559	0.096*
H45C	0.702850	0.637998	0.790294	0.096*
C13	1.111 (3)	0.140 (2)	0.773 (5)	0.085 (13)*
H13A	1.194802	0.175385	0.777975	0.128*
H13B	1.037034	0.177087	0.794720	0.128*
H13C	1.132302	0.090259	0.840122	0.128*
C7	0.947 (3)	0.2538 (15)	0.522 (4)	0.071 (10)*
H7A	0.850697	0.233091	0.519961	0.085*
H7B	0.984351	0.282286	0.611979	0.085*
C57	0.078 (3)	0.5494 (18)	0.401 (4)	0.064 (11)*
C47	0.034 (3)	0.5394 (14)	0.930 (4)	0.073 (10)*
H47A	0.087408	0.515801	1.020020	0.087*
H47B	−0.066477	0.537420	0.928944	0.087*
C38	0.427 (2)	0.9336 (13)	0.486 (5)	0.045 (8)*
H38	0.325158	0.944601	0.479198	0.054*
C26	0.560 (3)	0.361 (2)	0.635 (5)	0.062 (10)*
H26	0.619425	0.308848	0.624313	0.074*
C56	−0.058 (2)	0.6058 (15)	0.386 (6)	0.036 (7)*
H56	−0.133230	0.563729	0.395839	0.043*
C22	0.508 (3)	0.5233 (14)	0.536 (5)	0.072 (10)*
H22A	0.409439	0.515890	0.541391	0.086*
H22B	0.560219	0.549165	0.623259	0.086*
C52	0.057 (2)	0.7546 (13)	0.495 (5)	0.044 (8)*
H52A	0.152732	0.732998	0.499656	0.053*
H52B	0.022163	0.786947	0.406581	0.053*
C42	0.588 (3)	0.8292 (19)	0.386 (4)	0.062 (11)*
C6	0.944 (3)	0.3217 (19)	0.402 (4)	0.059 (10)*
H6A	1.039487	0.345249	0.410919	0.071*
H6B	0.882219	0.372224	0.411043	0.071*
C34	0.478 (3)	0.9543 (15)	0.749 (5)	0.058 (9)*
H34	0.376061	0.963679	0.743980	0.069*
C18	0.464 (3)	0.4208 (16)	0.099 (5)	0.087 (13)*
H18A	0.364576	0.438759	0.065206	0.104*
H18B	0.517026	0.448386	0.036721	0.104*
C37	0.496 (3)	1.0261 (15)	0.468 (6)	0.070 (10)*
H37A	0.595451	1.016589	0.467288	0.084*
H37B	0.448050	1.053489	0.378592	0.084*
C14	0.888 (3)	0.349 (2)	0.135 (5)	0.082 (10)*
H14A	0.854329	0.318490	0.047569	0.122*
H14B	0.824628	0.398080	0.140955	0.122*
H14C	0.982152	0.371575	0.140471	0.122*
C20	0.460 (4)	0.5520 (17)	0.266 (5)	0.084 (13)*
H20	0.357318	0.542818	0.255466	0.101*
C60	0.103 (3)	0.3840 (16)	0.867 (6)	0.073 (10)*
H60A	0.178289	0.385942	0.950631	0.110*
H60B	0.021288	0.354272	0.887990	0.110*
H60C	0.134153	0.350977	0.796280	0.110*
C30	0.340 (3)	0.1743 (17)	0.133 (5)	0.086 (11)*
H30A	0.269242	0.189863	0.049531	0.129*
H30B	0.408704	0.133195	0.110942	0.129*
H30C	0.295441	0.145969	0.200569	0.129*
C51	0.058 (3)	0.8179 (16)	0.616 (5)	0.044 (8)*
H51A	0.117800	0.869602	0.607914	0.053*
H51B	−0.038115	0.840373	0.609197	0.053*
C59	0.109 (3)	0.8394 (19)	0.875 (6)	0.080 (11)*
H59A	0.144366	0.809934	0.965123	0.120*
H59B	0.168727	0.890419	0.866750	0.120*
H59C	0.013100	0.859856	0.866977	0.120*
C35	0.543 (3)	1.0475 (16)	0.731 (6)	0.069 (9)*
H35	0.644878	1.036409	0.740592	0.083*
C58	−0.104 (3)	0.649 (2)	0.239 (6)	0.083 (11)*
H58A	−0.189547	0.683613	0.232151	0.125*
H58B	−0.029698	0.687231	0.222132	0.125*
H58C	−0.122083	0.601602	0.170536	0.125*
C2	0.973 (3)	0.0537 (14)	0.083 (5)	0.064 (9)*
H2A	0.924124	0.033162	−0.009492	0.077*
H2B	1.074939	0.052617	0.087061	0.077*
C28	0.617 (4)	0.395 (2)	0.785 (5)	0.095 (14)*
H28A	0.714594	0.413551	0.796360	0.142*
H28B	0.560230	0.445056	0.800700	0.142*
H28C	0.612620	0.346464	0.850469	0.142*
C21	0.513 (3)	0.5882 (19)	0.414 (5)	0.057 (10)*
H21A	0.611607	0.607348	0.425093	0.068*
H21B	0.457550	0.641768	0.422770	0.068*
C15	0.900 (3)	−0.1065 (15)	0.141 (5)	0.089 (12)*
H15A	0.824074	−0.101782	0.057619	0.133*
H15B	0.980508	−0.136855	0.119413	0.133*
H15C	0.868386	−0.140589	0.212038	0.133*
C44	0.533 (3)	1.1110 (18)	0.850 (6)	0.077 (10)*
H44A	0.569643	1.080463	0.939237	0.115*
H44B	0.588991	1.164255	0.844754	0.115*
H44C	0.435508	1.128220	0.842168	0.115*
C36	0.487 (3)	1.0904 (19)	0.586 (6)	0.063 (9)*
H36A	0.388521	1.108995	0.575229	0.076*
H36B	0.542298	1.144279	0.577241	0.076*
C43	0.383 (3)	0.903 (2)	0.218 (6)	0.088 (12)*
H43A	0.288016	0.927137	0.207022	0.132*
H43B	0.444468	0.949298	0.197431	0.132*
H43C	0.379831	0.853635	0.154198	0.132*
C29	0.471 (3)	0.6202 (19)	0.150 (5)	0.079 (10)*
H29A	0.435565	0.593156	0.059724	0.119*
H29B	0.414679	0.673147	0.156359	0.119*
H29C	0.568695	0.637176	0.159667	0.119*
C39	0.490 (2)	0.8900 (13)	0.632 (5)	0.035 (7)*
C41	0.439 (3)	0.8677 (17)	0.369 (5)	0.055 (9)*
H41	0.378656	0.815832	0.379923	0.066*
C31	0.589 (3)	0.7524 (14)	0.807 (4)	0.065 (10)*

Geometric parameters (Å, º) top

O9—C27	1.350 (15)	C23—C22	1.533 (14)
O9—C25	1.455 (15)	C23—C26	1.537 (15)
O8—C25	1.408 (15)	C23—H23	0.9800
O8—C16	1.442 (14)	C33—C34	1.521 (15)
O13—C31	1.422 (15)	C33—H33A	0.9700
O13—O14	1.478 (13)	C33—H33B	0.9700
O7—C16	1.417 (15)	C45—C31	1.507 (14)
O7—O6	1.468 (14)	C45—H45A	0.9600
O20—O19	1.460 (12)	C45—H45B	0.9600
O20—C54	1.476 (14)	C45—H45C	0.9600
O12—C42	1.340 (15)	C13—H13A	0.9600
O12—C40	1.444 (15)	C13—H13B	0.9600
O1—C9	1.466 (13)	C13—H13C	0.9600
O1—O2	1.469 (14)	C7—C6	1.527 (15)
O14—C39	1.448 (13)	C7—H7A	0.9700
O15—C40	1.407 (15)	C7—H7B	0.9700
O15—C31	1.449 (14)	C57—C56	1.523 (14)
O18—C55	1.401 (15)	C47—H47A	0.9700
O18—C46	1.438 (14)	C47—H47B	0.9700
O2—C1	1.414 (15)	C38—C39	1.537 (15)
O19—C46	1.411 (15)	C38—C41	1.542 (15)
O6—C24	1.459 (14)	C38—C37	1.544 (14)
O3—C10	1.408 (15)	C38—H38	0.9800
O3—C1	1.442 (14)	C26—C28	1.529 (15)
O17—C57	1.346 (15)	C26—H26	0.9800
O17—C55	1.441 (15)	C56—C58	1.522 (15)
O11—C42	1.206 (15)	C56—H56	0.9800
O4—C12	1.350 (15)	C22—C21	1.524 (15)
O4—C10	1.452 (15)	C22—H22A	0.9700
O16—C57	1.209 (15)	C22—H22B	0.9700
O10—C27	1.204 (15)	C52—C51	1.519 (15)
C16—C30	1.508 (15)	C52—H52A	0.9700
C16—C17	1.538 (15)	C52—H52B	0.9700
O5—C12	1.209 (15)	C42—C41	1.518 (14)
C9—C8	1.528 (15)	C6—H6A	0.9700
C9—C10	1.530 (14)	C6—H6B	0.9700
C9—C4	1.531 (15)	C34—C39	1.530 (15)
C54—C53	1.527 (15)	C34—C35	1.534 (14)
C54—C49	1.532 (15)	C34—H34	0.9800
C54—C55	1.538 (14)	C18—H18A	0.9700
C10—H10	0.9800	C18—H18B	0.9700
C24—C25	1.530 (14)	C37—C36	1.522 (15)
C24—C23	1.531 (15)	C37—H37A	0.9700
C24—C19	1.536 (15)	C37—H37B	0.9700
C46—C60	1.499 (14)	C14—H14A	0.9600
C46—C47	1.525 (15)	C14—H14B	0.9600
C25—H25	0.9800	C14—H14C	0.9600
C55—H55	0.9800	C20—C21	1.529 (15)
C12—C11	1.521 (15)	C20—C29	1.529 (15)
C1—C15	1.505 (15)	C20—H20	0.9800
C1—C2	1.528 (15)	C60—H60A	0.9600
C8—C7	1.527 (14)	C60—H60B	0.9600
C8—C11	1.539 (15)	C60—H60C	0.9600
C8—H8	0.9800	C30—H30A	0.9600
C3—C4	1.525 (15)	C30—H30B	0.9600
C3—C2	1.537 (14)	C30—H30C	0.9600
C3—H3A	0.9700	C51—H51A	0.9700
C3—H3B	0.9700	C51—H51B	0.9700
C48—C49	1.525 (15)	C59—H59A	0.9600
C48—C47	1.535 (14)	C59—H59B	0.9600
C48—H48A	0.9700	C59—H59C	0.9600
C48—H48B	0.9700	C35—C36	1.525 (15)
C49—C50	1.540 (14)	C35—C44	1.528 (15)
C49—H49	0.9800	C35—H35	0.9800
C40—C39	1.528 (14)	C58—H58A	0.9600
C40—H40	0.9800	C58—H58B	0.9600
C53—C56	1.528 (15)	C58—H58C	0.9600
C53—C52	1.541 (14)	C2—H2A	0.9700
C53—H53	0.9800	C2—H2B	0.9700
C50—C51	1.516 (15)	C28—H28A	0.9600
C50—C59	1.521 (15)	C28—H28B	0.9600
C50—H50	0.9800	C28—H28C	0.9600
C19—C18	1.529 (15)	C21—H21A	0.9700
C19—C20	1.532 (15)	C21—H21B	0.9700
C19—H19	0.9800	C15—H15A	0.9600
C32—C33	1.536 (14)	C15—H15B	0.9600
C32—C31	1.539 (15)	C15—H15C	0.9600
C32—H32A	0.9700	C44—H44A	0.9600
C32—H32B	0.9700	C44—H44B	0.9600
C4—C5	1.539 (14)	C44—H44C	0.9600
C4—H4	0.9800	C36—H36A	0.9700
C27—C26	1.521 (15)	C36—H36B	0.9700
C5—C14	1.522 (15)	C43—C41	1.531 (15)
C5—C6	1.527 (15)	C43—H43A	0.9600
C5—H5	0.9800	C43—H43B	0.9600
C11—C13	1.528 (15)	C43—H43C	0.9600
C11—H11	0.9800	C29—H29A	0.9600
C17—C18	1.526 (14)	C29—H29B	0.9600
C17—H17A	0.9700	C29—H29C	0.9600
C17—H17B	0.9700	C41—H41	0.9800

C27—O9—C25	120 (2)	C8—C7—H7B	110.1
C25—O8—C16	112 (2)	H7A—C7—H7B	108.4
C31—O13—O14	108 (2)	O16—C57—O17	120 (2)
C16—O7—O6	108 (2)	O16—C57—C56	119 (3)
O19—O20—C54	108.0 (14)	O17—C57—C56	120 (3)
C42—O12—C40	124.9 (18)	C46—C47—C48	113 (3)
C9—O1—O2	108.7 (17)	C46—C47—H47A	109.0
C39—O14—O13	109.5 (16)	C48—C47—H47A	109.0
C40—O15—C31	115 (2)	C46—C47—H47B	109.0
C55—O18—C46	115.5 (19)	C48—C47—H47B	109.0
C1—O2—O1	109.7 (19)	H47A—C47—H47B	107.8
C46—O19—O20	110 (2)	C39—C38—C41	111 (2)
C24—O6—O7	111.8 (17)	C39—C38—C37	112 (3)
C10—O3—C1	112 (2)	C41—C38—C37	112 (3)
C57—O17—C55	121.2 (17)	C39—C38—H38	107.5
C12—O4—C10	125 (2)	C41—C38—H38	107.5
O7—C16—O8	109 (2)	C37—C38—H38	107.5
O7—C16—C30	108 (3)	C27—C26—C28	115 (3)
O8—C16—C30	103 (2)	C27—C26—C23	106 (3)
O7—C16—C17	114 (3)	C28—C26—C23	115 (3)
O8—C16—C17	108 (2)	C27—C26—H26	106.6
C30—C16—C17	115 (2)	C28—C26—H26	106.6
O1—C9—C8	103 (2)	C23—C26—H26	106.6
O1—C9—C10	112.6 (18)	C58—C56—C57	111 (3)
C8—C9—C10	113 (2)	C58—C56—C53	114 (2)
O1—C9—C4	107.7 (19)	C57—C56—C53	111 (3)
C8—C9—C4	111 (2)	C58—C56—H56	106.7
C10—C9—C4	109 (2)	C57—C56—H56	106.7
O20—C54—C53	103 (2)	C53—C56—H56	106.7
O20—C54—C49	107 (3)	C21—C22—C23	112 (2)
C53—C54—C49	113.3 (16)	C21—C22—H22A	109.2
O20—C54—C55	112.4 (16)	C23—C22—H22A	109.2
C53—C54—C55	110 (2)	C21—C22—H22B	109.2
C49—C54—C55	111 (3)	C23—C22—H22B	109.2
O3—C10—O4	108 (2)	H22A—C22—H22B	107.9
O3—C10—C9	115 (2)	C51—C52—C53	110 (3)
O4—C10—C9	111 (2)	C51—C52—H52A	109.8
O3—C10—H10	107.8	C53—C52—H52A	109.8
O4—C10—H10	107.8	C51—C52—H52B	109.8
C9—C10—H10	107.8	C53—C52—H52B	109.8
O6—C24—C25	110.3 (18)	H52A—C52—H52B	108.2
O6—C24—C23	103 (2)	O11—C42—O12	120 (2)
C25—C24—C23	111 (3)	O11—C42—C41	124 (3)
O6—C24—C19	109 (2)	O12—C42—C41	116 (3)
C25—C24—C19	107 (2)	C7—C6—C5	114 (3)
C23—C24—C19	117 (2)	C7—C6—H6A	108.8
O19—C46—O18	104 (2)	C5—C6—H6A	108.8
O19—C46—C60	107 (3)	C7—C6—H6B	108.8
O18—C46—C60	104.4 (19)	C5—C6—H6B	108.8
O19—C46—C47	117 (2)	H6A—C6—H6B	107.7
O18—C46—C47	111 (3)	C33—C34—C39	112 (2)
C60—C46—C47	112 (3)	C33—C34—C35	110 (3)
O8—C25—O9	104 (2)	C39—C34—C35	112 (3)
O8—C25—C24	115 (2)	C33—C34—H34	107.5
O9—C25—C24	113 (2)	C39—C34—H34	107.5
O8—C25—H25	108.2	C35—C34—H34	107.5
O9—C25—H25	108.2	C17—C18—C19	114 (3)
C24—C25—H25	108.2	C17—C18—H18A	108.7
O18—C55—O17	104 (2)	C19—C18—H18A	108.7
O18—C55—C54	112 (2)	C17—C18—H18B	108.7
O17—C55—C54	115 (3)	C19—C18—H18B	108.7
O18—C55—H55	108.6	H18A—C18—H18B	107.6
O17—C55—H55	108.6	C36—C37—C38	112 (3)
C54—C55—H55	108.6	C36—C37—H37A	109.3
O5—C12—O4	122 (3)	C38—C37—H37A	109.3
O5—C12—C11	118 (3)	C36—C37—H37B	109.3
O4—C12—C11	120 (3)	C38—C37—H37B	109.3
O2—C1—O3	108 (2)	H37A—C37—H37B	107.9
O2—C1—C15	108 (2)	C5—C14—H14A	109.5
O3—C1—C15	102 (2)	C5—C14—H14B	109.5
O2—C1—C2	115 (3)	H14A—C14—H14B	109.5
O3—C1—C2	108 (2)	C5—C14—H14C	109.5
C15—C1—C2	115 (2)	H14A—C14—H14C	109.5
C7—C8—C9	113 (2)	H14B—C14—H14C	109.5
C7—C8—C11	113 (2)	C21—C20—C29	114 (3)
C9—C8—C11	110 (2)	C21—C20—C19	114 (3)
C7—C8—H8	106.8	C29—C20—C19	113 (2)
C9—C8—H8	106.8	C21—C20—H20	104.9
C11—C8—H8	106.8	C29—C20—H20	104.9
C4—C3—C2	118 (3)	C19—C20—H20	104.9
C4—C3—H3A	107.8	C46—C60—H60A	109.5
C2—C3—H3A	107.8	C46—C60—H60B	109.5
C4—C3—H3B	107.8	H60A—C60—H60B	109.5
C2—C3—H3B	107.8	C46—C60—H60C	109.5
H3A—C3—H3B	107.1	H60A—C60—H60C	109.5
C49—C48—C47	119 (3)	H60B—C60—H60C	109.5
C49—C48—H48A	107.5	C16—C30—H30A	109.5
C47—C48—H48A	107.5	C16—C30—H30B	109.5
C49—C48—H48B	107.5	H30A—C30—H30B	109.5
C47—C48—H48B	107.5	C16—C30—H30C	109.5
H48A—C48—H48B	107.0	H30A—C30—H30C	109.5
C48—C49—C54	112.6 (19)	H30B—C30—H30C	109.5
C48—C49—C50	112 (3)	C50—C51—C52	113.1 (19)
C54—C49—C50	113 (3)	C50—C51—H51A	109.0
C48—C49—H49	106.4	C52—C51—H51A	109.0
C54—C49—H49	106.4	C50—C51—H51B	109.0
C50—C49—H49	106.4	C52—C51—H51B	109.0
O15—C40—O12	108 (2)	H51A—C51—H51B	107.8
O15—C40—C39	111 (2)	C50—C59—H59A	109.5
O12—C40—C39	114 (3)	C50—C59—H59B	109.5
O15—C40—H40	108.0	H59A—C59—H59B	109.5
O12—C40—H40	108.0	C50—C59—H59C	109.5
C39—C40—H40	108.0	H59A—C59—H59C	109.5
C54—C53—C56	110.3 (18)	H59B—C59—H59C	109.5
C54—C53—C52	110 (3)	C36—C35—C44	113 (2)
C56—C53—C52	115 (3)	C36—C35—C34	114 (3)
C54—C53—H53	107.1	C44—C35—C34	112 (3)
C56—C53—H53	107.1	C36—C35—H35	105.8
C52—C53—H53	107.1	C44—C35—H35	105.8
C51—C50—C59	110 (2)	C34—C35—H35	105.8
C51—C50—C49	110 (3)	C56—C58—H58A	109.5
C59—C50—C49	111 (3)	C56—C58—H58B	109.5
C51—C50—H50	108.4	H58A—C58—H58B	109.5
C59—C50—H50	108.4	C56—C58—H58C	109.5
C49—C50—H50	108.4	H58A—C58—H58C	109.5
C18—C19—C20	114 (3)	H58B—C58—H58C	109.5
C18—C19—C24	117 (3)	C1—C2—C3	115 (3)
C20—C19—C24	111 (2)	C1—C2—H2A	108.6
C18—C19—H19	104.7	C3—C2—H2A	108.6
C20—C19—H19	104.7	C1—C2—H2B	108.6
C24—C19—H19	104.7	C3—C2—H2B	108.6
C33—C32—C31	116 (3)	H2A—C2—H2B	107.5
C33—C32—H32A	108.4	C26—C28—H28A	109.5
C31—C32—H32A	108.4	C26—C28—H28B	109.5
C33—C32—H32B	108.4	H28A—C28—H28B	109.5
C31—C32—H32B	108.4	C26—C28—H28C	109.5
H32A—C32—H32B	107.4	H28A—C28—H28C	109.5
C3—C4—C9	113 (2)	H28B—C28—H28C	109.5
C3—C4—C5	113 (3)	C22—C21—C20	117 (3)
C9—C4—C5	114 (2)	C22—C21—H21A	108.1
C3—C4—H4	105.6	C20—C21—H21A	108.1
C9—C4—H4	105.6	C22—C21—H21B	108.1
C5—C4—H4	105.6	C20—C21—H21B	108.1
O10—C27—O9	119 (3)	H21A—C21—H21B	107.3
O10—C27—C26	117 (3)	C1—C15—H15A	109.5
O9—C27—C26	123 (3)	C1—C15—H15B	109.5
C14—C5—C6	115 (2)	H15A—C15—H15B	109.5
C14—C5—C4	111 (2)	C1—C15—H15C	109.5
C6—C5—C4	111 (3)	H15A—C15—H15C	109.5
C14—C5—H5	106.5	H15B—C15—H15C	109.5
C6—C5—H5	106.5	C35—C44—H44A	109.5
C4—C5—H5	106.5	C35—C44—H44B	109.5
C12—C11—C13	114 (3)	H44A—C44—H44B	109.5
C12—C11—C8	110 (2)	C35—C44—H44C	109.5
C13—C11—C8	115 (3)	H44A—C44—H44C	109.5
C12—C11—H11	105.6	H44B—C44—H44C	109.5
C13—C11—H11	105.6	C37—C36—C35	113 (2)
C8—C11—H11	105.6	C37—C36—H36A	109.1
C18—C17—C16	118 (3)	C35—C36—H36A	109.1
C18—C17—H17A	107.8	C37—C36—H36B	109.1
C16—C17—H17A	107.8	C35—C36—H36B	109.1
C18—C17—H17B	107.8	H36A—C36—H36B	107.8
C16—C17—H17B	107.8	C41—C43—H43A	109.5
H17A—C17—H17B	107.1	C41—C43—H43B	109.5
C24—C23—C22	112 (3)	H43A—C43—H43B	109.5
C24—C23—C26	113 (3)	C41—C43—H43C	109.5
C22—C23—C26	113 (2)	H43A—C43—H43C	109.5
C24—C23—H23	106.1	H43B—C43—H43C	109.5
C22—C23—H23	106.1	C20—C29—H29A	109.5
C26—C23—H23	106.1	C20—C29—H29B	109.5
C34—C33—C32	118 (3)	H29A—C29—H29B	109.5
C34—C33—H33A	107.9	C20—C29—H29C	109.5
C32—C33—H33A	107.9	H29A—C29—H29C	109.5
C34—C33—H33B	107.9	H29B—C29—H29C	109.5
C32—C33—H33B	107.9	O14—C39—C40	113.0 (16)
H33A—C33—H33B	107.2	O14—C39—C34	107 (3)
C31—C45—H45A	109.5	C40—C39—C34	113 (3)
C31—C45—H45B	109.5	O14—C39—C38	103 (3)
H45A—C45—H45B	109.5	C40—C39—C38	109 (3)
C31—C45—H45C	109.5	C34—C39—C38	111.1 (18)
H45A—C45—H45C	109.5	C42—C41—C43	109 (3)
H45B—C45—H45C	109.5	C42—C41—C38	113 (3)
C11—C13—H13A	109.5	C43—C41—C38	116 (2)
C11—C13—H13B	109.5	C42—C41—H41	105.7
H13A—C13—H13B	109.5	C43—C41—H41	105.7
C11—C13—H13C	109.5	C38—C41—H41	105.7
H13A—C13—H13C	109.5	O13—C31—O15	106 (2)
H13B—C13—H13C	109.5	O13—C31—C45	106 (3)
C6—C7—C8	108 (2)	O15—C31—C45	104.9 (19)
C6—C7—H7A	110.1	O13—C31—C32	114 (2)
C8—C7—H7A	110.1	O15—C31—C32	108 (2)
C6—C7—H7B	110.1	C45—C31—C32	117 (3)

C31—O13—O14—C39	48 (4)	O4—C12—C11—C8	34 (4)
C9—O1—O2—C1	48 (3)	C7—C8—C11—C12	77 (3)
C54—O20—O19—C46	50 (4)	C9—C8—C11—C12	−50 (3)
C16—O7—O6—C24	48 (3)	C7—C8—C11—C13	−54 (3)
O6—O7—C16—O8	−75 (3)	C9—C8—C11—C13	179 (2)
O6—O7—C16—C30	172.8 (19)	O7—C16—C17—C18	−94 (3)
O6—O7—C16—C17	45 (2)	O8—C16—C17—C18	27 (4)
C25—O8—C16—O7	35 (3)	C30—C16—C17—C18	141 (3)
C25—O8—C16—C30	150 (2)	O6—C24—C23—C22	170.3 (18)
C25—O8—C16—C17	−89 (3)	C25—C24—C23—C22	−72 (3)
O2—O1—C9—C8	134 (2)	C19—C24—C23—C22	51 (3)
O2—O1—C9—C10	12 (3)	O6—C24—C23—C26	−61 (2)
O2—O1—C9—C4	−109 (2)	C25—C24—C23—C26	57 (2)
O19—O20—C54—C53	132 (2)	C19—C24—C23—C26	179.7 (18)
O19—O20—C54—C49	−109 (2)	C31—C32—C33—C34	53 (3)
O19—O20—C54—C55	14 (5)	C9—C8—C7—C6	−57 (3)
C1—O3—C10—O4	−98 (2)	C11—C8—C7—C6	177 (3)
C1—O3—C10—C9	26 (3)	C55—O17—C57—O16	160 (2)
C12—O4—C10—O3	154 (2)	C55—O17—C57—C56	−30 (4)
C12—O4—C10—C9	28 (3)	O19—C46—C47—C48	−89 (3)
O1—C9—C10—O3	−51 (3)	O18—C46—C47—C48	31 (3)
C8—C9—C10—O3	−166.9 (17)	C60—C46—C47—C48	147 (3)
C4—C9—C10—O3	68 (2)	C49—C48—C47—C46	51 (3)
O1—C9—C10—O4	71 (3)	O10—C27—C26—C28	−26 (4)
C8—C9—C10—O4	−45 (3)	O9—C27—C26—C28	169 (3)
C4—C9—C10—O4	−169.2 (19)	O10—C27—C26—C23	−154 (3)
O7—O6—C24—C25	11 (4)	O9—C27—C26—C23	40 (4)
O7—O6—C24—C23	130 (2)	C24—C23—C26—C27	−51 (3)
O7—O6—C24—C19	−105 (3)	C22—C23—C26—C27	77 (4)
O20—O19—C46—O18	−79 (2)	C24—C23—C26—C28	−180 (2)
O20—O19—C46—C60	170 (2)	C22—C23—C26—C28	−52 (4)
O20—O19—C46—C47	43 (2)	O16—C57—C56—C58	−23 (4)
C55—O18—C46—O19	37 (3)	O17—C57—C56—C58	167 (3)
C55—O18—C46—C60	150 (3)	O16—C57—C56—C53	−151 (3)
C55—O18—C46—C47	−89 (3)	O17—C57—C56—C53	39 (3)
C16—O8—C25—O9	−97.4 (19)	C54—C53—C56—C58	−178.4 (19)
C16—O8—C25—C24	27 (3)	C52—C53—C56—C58	−54 (3)
C27—O9—C25—O8	161 (2)	C54—C53—C56—C57	−52 (3)
C27—O9—C25—C24	35 (3)	C52—C53—C56—C57	73 (3)
O6—C24—C25—O8	−51 (3)	C24—C23—C22—C21	−48 (3)
C23—C24—C25—O8	−164.7 (18)	C26—C23—C22—C21	−177 (3)
C19—C24—C25—O8	67 (3)	C54—C53—C52—C51	−57 (2)
O6—C24—C25—O9	68 (3)	C56—C53—C52—C51	177.7 (18)
C23—C24—C25—O9	−46 (3)	C40—O12—C42—O11	157 (2)
C19—C24—C25—O9	−174 (2)	C40—O12—C42—C41	−28 (4)
C46—O18—C55—O17	−101 (3)	C8—C7—C6—C5	57 (3)
C46—O18—C55—C54	24 (4)	C14—C5—C6—C7	179.7 (18)
C57—O17—C55—O18	156 (2)	C4—C5—C6—C7	−53 (3)
C57—O17—C55—C54	34 (3)	C32—C33—C34—C39	−34 (3)
O20—C54—C55—O18	−52 (5)	C32—C33—C34—C35	−159 (3)
C53—C54—C55—O18	−165 (2)	C16—C17—C18—C19	51 (4)
C49—C54—C55—O18	69 (3)	C20—C19—C18—C17	−158 (2)
O20—C54—C55—O17	67 (4)	C24—C19—C18—C17	−27 (4)
C53—C54—C55—O17	−47 (2)	C39—C38—C37—C36	−54 (3)
C49—C54—C55—O17	−172.8 (18)	C41—C38—C37—C36	−179 (2)
C10—O4—C12—O5	159 (2)	C18—C19—C20—C21	179 (3)
C10—O4—C12—C11	−24 (4)	C24—C19—C20—C21	45 (4)
O1—O2—C1—O3	−77 (2)	C18—C19—C20—C29	−49 (4)
O1—O2—C1—C15	173.7 (18)	C24—C19—C20—C29	177 (3)
O1—O2—C1—C2	44 (2)	C59—C50—C51—C52	−179.2 (19)
C10—O3—C1—O2	35 (3)	C49—C50—C51—C52	−56 (3)
C10—O3—C1—C15	148 (2)	C53—C52—C51—C50	60 (3)
C10—O3—C1—C2	−90 (3)	C33—C34—C35—C36	176 (2)
O1—C9—C8—C7	169.4 (18)	C39—C34—C35—C36	51 (3)
C10—C9—C8—C7	−69 (2)	C33—C34—C35—C44	−54 (3)
C4—C9—C8—C7	54 (2)	C39—C34—C35—C44	−179 (2)
O1—C9—C8—C11	−63 (2)	O2—C1—C2—C3	−90 (3)
C10—C9—C8—C11	58 (2)	O3—C1—C2—C3	31 (4)
C4—C9—C8—C11	−178.2 (15)	C15—C1—C2—C3	144 (3)
C47—C48—C49—C54	−33 (3)	C4—C3—C2—C1	52 (4)
C47—C48—C49—C50	−162 (3)	C23—C22—C21—C20	48 (4)
O20—C54—C49—C48	69 (2)	C29—C20—C21—C22	−179.1 (19)
C53—C54—C49—C48	−178.9 (16)	C19—C20—C21—C22	−47 (4)
C55—C54—C49—C48	−55 (2)	C38—C37—C36—C35	51 (3)
O20—C54—C49—C50	−164 (3)	C44—C35—C36—C37	−180 (2)
C53—C54—C49—C50	−51 (3)	C34—C35—C36—C37	−50 (3)
C55—C54—C49—C50	73 (2)	O13—O14—C39—C40	15 (5)
C31—O15—C40—O12	−97 (3)	O13—O14—C39—C34	−111 (3)
C31—O15—C40—C39	28 (3)	O13—O14—C39—C38	132 (3)
C42—O12—C40—O15	158 (2)	O15—C40—C39—O14	−54 (5)
C42—O12—C40—C39	35 (3)	O12—C40—C39—O14	68 (4)
O20—C54—C53—C56	−63 (2)	O15—C40—C39—C34	68 (2)
C49—C54—C53—C56	−178.2 (16)	O12—C40—C39—C34	−170.2 (19)
C55—C54—C53—C56	57 (2)	O15—C40—C39—C38	−168 (2)
O20—C54—C53—C52	169 (3)	O12—C40—C39—C38	−46 (2)
C49—C54—C53—C52	54 (2)	C33—C34—C39—O14	70 (3)
C55—C54—C53—C52	−71 (2)	C35—C34—C39—O14	−166 (3)
C48—C49—C50—C51	178.5 (19)	C33—C34—C39—C40	−55 (3)
C54—C49—C50—C51	50 (2)	C35—C34—C39—C40	69 (3)
C48—C49—C50—C59	−59 (3)	C33—C34—C39—C38	−177.9 (18)
C54—C49—C50—C59	173 (2)	C35—C34—C39—C38	−53 (3)
O6—C24—C19—C18	62 (3)	C41—C38—C39—O14	−65 (2)
C25—C24—C19—C18	−57 (3)	C37—C38—C39—O14	170 (3)
C23—C24—C19—C18	179 (2)	C41—C38—C39—C40	56 (3)
O6—C24—C19—C20	−165 (3)	C37—C38—C39—C40	−70 (3)
C25—C24—C19—C20	76 (3)	C41—C38—C39—C34	−179.5 (18)
C23—C24—C19—C20	−49 (3)	C37—C38—C39—C34	55 (3)
C2—C3—C4—C9	−33 (3)	O11—C42—C41—C43	−19 (4)
C2—C3—C4—C5	−163 (2)	O12—C42—C41—C43	167 (2)
O1—C9—C4—C3	69 (3)	O11—C42—C41—C38	−150 (3)
C8—C9—C4—C3	−179 (2)	O12—C42—C41—C38	36 (4)
C10—C9—C4—C3	−54 (3)	C39—C38—C41—C42	−51 (3)
O1—C9—C4—C5	−161 (3)	C37—C38—C41—C42	74 (3)
C8—C9—C4—C5	−49 (3)	C39—C38—C41—C43	−179 (2)
C10—C9—C4—C5	76 (3)	C37—C38—C41—C43	−54 (3)
C25—O9—C27—O10	161 (2)	O14—O13—C31—O15	−75 (2)
C25—O9—C27—C26	−34 (4)	O14—O13—C31—C45	173 (2)
C3—C4—C5—C14	−53 (3)	O14—O13—C31—C32	43 (2)
C9—C4—C5—C14	177 (3)	C40—O15—C31—O13	33 (3)
C3—C4—C5—C6	179 (2)	C40—O15—C31—C45	145 (3)
C9—C4—C5—C6	49 (3)	C40—O15—C31—C32	−90 (3)
O5—C12—C11—C13	−18 (4)	C33—C32—C31—O13	−90 (3)
O4—C12—C11—C13	165 (3)	C33—C32—C31—O15	27 (4)
O5—C12—C11—C8	−149 (3)	C33—C32—C31—C45	145 (3)

(FormII_5) top

Crystal data top

C₁₅H₂₂O₅	Z = 4
M_r = 282.32	F(000) = 608
Triclinic, P1	D_x = 1.411 Mg m⁻³
a = 9.579 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.679 (5) Å	Cell parameters from 3350 reflections
c = 9.737 (7) Å	θ = 2.2–23.3°
α = 88.89 (5)°	µ = 0.11 mm⁻¹
β = 103.90 (4)°	T = 296 K
γ = 89.854 (18)°	Plate, clear colourless
V = 1328.7 (11) Å³	0.12 × 0.06 × 0.05 mm

Data collection top

Bruker Photon III diffractometer	1887 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	888 reflections with I > 2σ(I)
Mirror optics monochromator	R_int = 0.059
Detector resolution: 7.9 pixels mm^-1	θ_max = 23.3°, θ_min = 2.2°
ω scans	h = −10→10
Absorption correction: multi-scan	k = −16→14
T_min = 0.618, T_max = 0.745	l = −5→5
3350 measured 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)] = 0.080	w = 1/[σ²(F_o²) + (0.1101P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.227	(Δ/σ)_max < 0.001
S = 1.03	Δρ_max = 0.18 e Å⁻³
1887 reflections	Δρ_min = −0.16 e Å⁻³
321 parameters	Absolute structure: Flack x determined using 287 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
95 restraints	Absolute structure parameter: −1.0 (10)

Special details top

Refinement. CX-ASAP (Thompson, 2023)

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

	x	y	z	U_iso*/U_eq
O9	0.332 (2)	0.3111 (16)	0.470 (5)	0.050 (8)*
O8	0.303 (2)	0.3132 (15)	0.232 (5)	0.043 (8)*
O13	0.482 (3)	0.7279 (16)	0.686 (6)	0.063 (8)*
O7	0.518 (2)	0.2357 (16)	0.302 (5)	0.061 (8)*
O20	−0.113 (2)	0.5586 (14)	0.642 (5)	0.047 (7)*
O12	0.661 (3)	0.8115 (16)	0.518 (6)	0.052 (8)*
O1	1.113 (2)	0.0667 (14)	0.364 (5)	0.031 (6)*
O14	0.397 (2)	0.8124 (14)	0.636 (6)	0.062 (8)*
O15	0.698 (3)	0.8038 (16)	0.758 (6)	0.056 (8)*
O18	0.181 (2)	0.5092 (17)	0.763 (5)	0.045 (7)*
O2	1.056 (3)	−0.0215 (17)	0.309 (5)	0.060 (8)*
O19	−0.053 (3)	0.4690 (16)	0.693 (5)	0.062 (8)*
O6	0.603 (2)	0.3159 (13)	0.360 (5)	0.049 (7)*
O3	0.812 (3)	0.0183 (18)	0.233 (5)	0.064 (9)*
O17	0.147 (3)	0.5216 (18)	0.530 (6)	0.062 (9)*
O11	0.634 (3)	0.8108 (16)	0.284 (6)	0.073 (10)*
O4	0.852 (3)	0.0219 (17)	0.479 (5)	0.056 (9)*
O16	0.104 (3)	0.5193 (18)	0.293 (6)	0.071 (9)*
O10	0.359 (3)	0.3022 (17)	0.698 (5)	0.058 (8)*
C16	0.409 (3)	0.261 (2)	0.181 (4)	0.050 (12)*
O5	0.897 (3)	0.0115 (19)	0.711 (6)	0.067 (9)*
C9	0.993 (2)	0.1285 (17)	0.364 (5)	0.038 (11)*
C54	0.007 (3)	0.6215 (19)	0.656 (8)	0.047 (11)*
C10	0.855 (3)	0.073 (2)	0.352 (5)	0.034 (10)*
H10	0.778378	0.119094	0.342635	0.040*
C24	0.511 (3)	0.3939 (17)	0.372 (5)	0.040 (12)*
C46	0.060 (3)	0.479 (2)	0.815 (5)	0.049 (12)*
C25	0.354 (2)	0.366 (3)	0.353 (4)	0.038 (11)*
H25	0.294987	0.420892	0.344004	0.046*
C55	0.150 (4)	0.574 (3)	0.653 (5)	0.073 (16)*
H55	0.226964	0.619415	0.665536	0.087*
C12	0.931 (4)	0.043 (2)	0.609 (5)	0.058 (15)*
C1	0.938 (3)	−0.013 (2)	0.190 (5)	0.064 (14)*
C8	1.045 (3)	0.172 (2)	0.509 (5)	0.031 (10)*
H8	1.140383	0.197341	0.512841	0.037*
C3	0.927 (4)	0.152 (2)	0.096 (6)	0.065 (15)*
H3A	0.961257	0.188831	0.027259	0.078*
H3B	0.822769	0.155081	0.069299	0.078*
C48	0.075 (4)	0.636 (2)	0.911 (8)	0.072 (15)*
H48A	0.049706	0.671341	0.985503	0.086*
H48B	0.179281	0.635314	0.931477	0.086*
C49	0.023 (4)	0.691 (2)	0.774 (7)	0.055 (12)*
H49	−0.074148	0.713435	0.772526	0.066*
C40	0.642 (3)	0.860 (3)	0.639 (5)	0.057 (13)*
H40	0.701350	0.914953	0.647382	0.068*
C53	−0.033 (3)	0.6716 (19)	0.513 (8)	0.021 (8)*
H53	−0.128533	0.696994	0.508432	0.025*
C50	0.120 (4)	0.776 (2)	0.785 (7)	0.055 (12)*
H50	0.217795	0.753816	0.791444	0.066*
C19	0.523 (4)	0.460 (2)	0.252 (6)	0.056 (13)*
H19	0.626179	0.470812	0.262280	0.067*
C32	0.534 (4)	0.809 (2)	0.913 (6)	0.056 (12)*
H32A	0.433828	0.793871	0.901789	0.068*
H32B	0.585187	0.788352	1.006843	0.068*
C4	0.977 (4)	0.197 (2)	0.239 (5)	0.041 (11)*
H4	1.074095	0.218579	0.242819	0.050*
C27	0.406 (4)	0.332 (3)	0.601 (5)	0.063 (16)*
C5	0.888 (4)	0.282 (2)	0.253 (6)	0.032 (11)*
H5	0.787614	0.263960	0.243073	0.039*
C11	1.063 (3)	0.102 (2)	0.632 (6)	0.036 (10)*
H11	1.141556	0.061227	0.622011	0.043*
C17	0.471 (4)	0.320 (2)	0.078 (6)	0.060 (13)*
H17A	0.569409	0.301494	0.085289	0.072*
H17B	0.416502	0.308546	−0.017988	0.072*
C23	0.575 (4)	0.434 (2)	0.518 (5)	0.043 (12)*
H23	0.677232	0.445454	0.526845	0.051*
C33	0.547 (4)	0.912 (2)	0.904 (7)	0.087 (16)*
H33A	0.647678	0.927938	0.930701	0.104*
H33B	0.501048	0.938234	0.973346	0.104*
C45	0.656 (4)	0.660 (2)	0.847 (10)	0.077 (14)*
H45A	0.734477	0.664536	0.929465	0.115*
H45B	0.584228	0.620123	0.868588	0.115*
H45C	0.690818	0.635433	0.770889	0.115*
C13	1.112 (6)	0.142 (4)	0.779 (6)	0.14 (3)*
H13A	1.196113	0.178513	0.783175	0.214*
H13B	1.036212	0.180280	0.796352	0.214*
H13C	1.133157	0.094273	0.848676	0.214*
C7	0.947 (4)	0.253 (2)	0.523 (6)	0.060 (13)*
H7A	0.850843	0.231307	0.520649	0.072*
H7B	0.983911	0.282404	0.612877	0.072*
C57	0.077 (4)	0.548 (3)	0.398 (6)	0.08 (2)*
C47	0.028 (4)	0.538 (2)	0.930 (6)	0.066 (14)*
H47A	0.078391	0.513941	1.022565	0.080*
H47B	−0.074572	0.536794	0.925769	0.080*
C38	0.432 (3)	0.935 (2)	0.489 (7)	0.055 (12)*
H38	0.329952	0.947998	0.480919	0.066*
C26	0.560 (3)	0.364 (3)	0.633 (6)	0.055 (14)*
H26	0.618425	0.310749	0.620724	0.066*
C56	−0.060 (4)	0.601 (3)	0.395 (8)	0.061 (13)*
H56	−0.135875	0.559153	0.407520	0.073*
C22	0.502 (4)	0.525 (2)	0.535 (7)	0.078 (15)*
H22A	0.401512	0.514838	0.534907	0.093*
H22B	0.548985	0.552293	0.623572	0.093*
C52	0.060 (3)	0.7559 (19)	0.507 (7)	0.042 (11)*
H52A	0.157565	0.737001	0.507637	0.050*
H52B	0.021749	0.790835	0.421039	0.050*
C42	0.589 (4)	0.831 (3)	0.385 (6)	0.08 (2)*
C6	0.943 (4)	0.320 (3)	0.401 (6)	0.055 (14)*
H6A	0.883392	0.371510	0.411233	0.066*
H6B	1.039982	0.342592	0.408640	0.066*
C34	0.479 (4)	0.955 (2)	0.759 (7)	0.047 (11)*
H34	0.377486	0.966850	0.753965	0.057*
C18	0.466 (4)	0.422 (2)	0.105 (6)	0.054 (13)*
H18A	0.518230	0.452090	0.042826	0.065*
H18B	0.366633	0.441515	0.072975	0.065*
C37	0.499 (4)	1.026 (2)	0.462 (8)	0.075 (15)*
H37A	0.598450	1.017263	0.458386	0.090*
H37B	0.446801	1.052853	0.372268	0.090*
C14	0.893 (4)	0.353 (3)	0.139 (6)	0.063 (13)*
H14A	0.857362	0.327083	0.047713	0.095*
H14B	0.834265	0.404484	0.148904	0.095*
H14C	0.990381	0.372389	0.148498	0.095*
C20	0.454 (5)	0.554 (2)	0.260 (7)	0.075 (17)*
H20	0.351031	0.544017	0.248609	0.090*
C60	0.101 (4)	0.382 (2)	0.866 (9)	0.073 (14)*
H60A	0.177962	0.382891	0.949342	0.109*
H60B	0.018848	0.352544	0.887348	0.109*
H60C	0.130435	0.349447	0.793183	0.109*
C30	0.342 (3)	0.171 (2)	0.131 (7)	0.052 (11)*
H30A	0.265785	0.181265	0.048020	0.078*
H30B	0.414075	0.132370	0.108829	0.078*
H30C	0.304742	0.143231	0.204231	0.078*
C51	0.063 (4)	0.815 (3)	0.635 (7)	0.048 (11)*
H51A	−0.035086	0.835439	0.628051	0.057*
H51B	0.119014	0.868315	0.626192	0.057*
C59	0.126 (5)	0.842 (4)	0.904 (8)	0.13 (2)*
H59A	0.163271	0.811565	0.993721	0.192*
H59B	0.188382	0.892004	0.894332	0.192*
H59C	0.031567	0.865455	0.900536	0.192*
C35	0.549 (4)	1.044 (2)	0.728 (8)	0.064 (13)*
H35	0.651581	1.032060	0.737710	0.077*
C58	−0.105 (4)	0.650 (3)	0.251 (9)	0.060 (13)*
H58A	−0.191530	0.684248	0.246475	0.090*
H58B	−0.029929	0.690246	0.239733	0.090*
H58C	−0.121975	0.605767	0.177847	0.090*
C2	0.970 (4)	0.053 (2)	0.078 (7)	0.066 (14)*
H2A	0.918892	0.032456	−0.015095	0.079*
H2B	1.072122	0.050031	0.081669	0.079*
C28	0.616 (4)	0.394 (3)	0.786 (7)	0.086 (19)*
H28A	0.713940	0.412814	0.799842	0.129*
H28B	0.557984	0.443124	0.803985	0.129*
H28C	0.610731	0.343313	0.848749	0.129*
C21	0.513 (4)	0.586 (3)	0.411 (7)	0.055 (14)*
H21A	0.613783	0.600320	0.421251	0.066*
H21B	0.464501	0.643332	0.419996	0.066*
C15	0.905 (4)	−0.107 (2)	0.135 (8)	0.081 (15)*
H15A	0.825088	−0.104590	0.053905	0.121*
H15B	0.987653	−0.131678	0.108908	0.121*
H15C	0.881492	−0.145064	0.207521	0.121*
C44	0.537 (4)	1.110 (3)	0.844 (8)	0.069 (13)*
H44A	0.574207	1.081544	0.935090	0.104*
H44B	0.590564	1.164196	0.835897	0.104*
H44C	0.437479	1.126114	0.834450	0.104*
C36	0.490 (4)	1.088 (3)	0.583 (8)	0.067 (13)*
H36A	0.390495	1.105530	0.573745	0.081*
H36B	0.543585	1.143426	0.575055	0.081*
C43	0.390 (4)	0.905 (3)	0.227 (7)	0.062 (13)*
H43A	0.292933	0.927941	0.212119	0.093*
H43B	0.452530	0.953936	0.216384	0.093*
H43C	0.392989	0.858978	0.159467	0.093*
C29	0.468 (4)	0.623 (3)	0.143 (7)	0.074 (14)*
H29A	0.428530	0.596697	0.052131	0.111*
H29B	0.416440	0.677447	0.151768	0.111*
H29C	0.567605	0.636306	0.151681	0.111*
C39	0.488 (3)	0.8913 (19)	0.638 (7)	0.045 (11)*
C41	0.437 (3)	0.864 (3)	0.377 (7)	0.053 (12)*
H41	0.376194	0.812090	0.387137	0.064*
C31	0.591 (4)	0.753 (2)	0.805 (5)	0.065 (13)*

Geometric parameters (Å, º) top

O9—C27	1.348 (15)	C23—C22	1.530 (15)
O9—C25	1.442 (15)	C23—C26	1.537 (15)
O8—C25	1.403 (15)	C23—H23	0.9800
O8—C16	1.447 (15)	C33—C34	1.528 (16)
O13—C31	1.423 (16)	C33—H33A	0.9700
O13—O14	1.488 (14)	C33—H33B	0.9700
O7—C16	1.417 (15)	C45—C31	1.506 (15)
O7—O6	1.474 (15)	C45—H45A	0.9600
O20—O19	1.463 (14)	C45—H45B	0.9600
O20—C54	1.465 (15)	C45—H45C	0.9600
O12—C42	1.339 (15)	C13—H13A	0.9600
O12—C40	1.442 (15)	C13—H13B	0.9600
O1—C9	1.465 (14)	C13—H13C	0.9600
O1—O2	1.470 (15)	C7—C6	1.526 (15)
O14—C39	1.453 (15)	C7—H7A	0.9700
O15—C40	1.406 (15)	C7—H7B	0.9700
O15—C31	1.430 (15)	C57—C56	1.516 (15)
O18—C55	1.400 (15)	C47—H47A	0.9700
O18—C46	1.438 (15)	C47—H47B	0.9700
O2—C1	1.411 (15)	C38—C37	1.530 (15)
O19—C46	1.412 (16)	C38—C41	1.540 (15)
O6—C24	1.463 (15)	C38—C39	1.541 (15)
O3—C10	1.406 (15)	C38—H38	0.9800
O3—C1	1.441 (15)	C26—C28	1.528 (16)
O17—C57	1.342 (15)	C26—H26	0.9800
O17—C55	1.439 (15)	C56—C58	1.527 (16)
O11—C42	1.202 (15)	C56—H56	0.9800
O4—C12	1.345 (15)	C22—C21	1.523 (16)
O4—C10	1.442 (15)	C22—H22A	0.9700
O16—C57	1.205 (15)	C22—H22B	0.9700
O10—C27	1.209 (15)	C52—C51	1.525 (16)
C16—C30	1.504 (15)	C52—H52A	0.9700
C16—C17	1.535 (15)	C52—H52B	0.9700
O5—C12	1.208 (15)	C42—C41	1.517 (15)
C9—C10	1.532 (15)	C6—H6A	0.9700
C9—C8	1.536 (15)	C6—H6B	0.9700
C9—C4	1.538 (15)	C34—C35	1.536 (15)
C54—C53	1.531 (15)	C34—C39	1.538 (15)
C54—C55	1.533 (15)	C34—H34	0.9800
C54—C49	1.535 (15)	C18—H18A	0.9700
C10—H10	0.9800	C18—H18B	0.9700
C24—C25	1.529 (15)	C37—C36	1.521 (16)
C24—C23	1.533 (15)	C37—H37A	0.9700
C24—C19	1.534 (15)	C37—H37B	0.9700
C46—C60	1.514 (15)	C14—H14A	0.9600
C46—C47	1.524 (16)	C14—H14B	0.9600
C25—H25	0.9800	C14—H14C	0.9600
C55—H55	0.9800	C20—C21	1.528 (16)
C12—C11	1.511 (15)	C20—C29	1.530 (16)
C1—C15	1.500 (15)	C20—H20	0.9800
C1—C2	1.528 (15)	C60—H60A	0.9600
C8—C7	1.534 (15)	C60—H60B	0.9600
C8—C11	1.540 (15)	C60—H60C	0.9600
C8—H8	0.9800	C30—H30A	0.9600
C3—C4	1.527 (16)	C30—H30B	0.9600
C3—C2	1.536 (15)	C30—H30C	0.9600
C3—H3A	0.9700	C51—H51A	0.9700
C3—H3B	0.9700	C51—H51B	0.9700
C48—C49	1.525 (16)	C59—H59A	0.9600
C48—C47	1.537 (15)	C59—H59B	0.9600
C48—H48A	0.9700	C59—H59C	0.9600
C48—H48B	0.9700	C35—C36	1.522 (16)
C49—C50	1.537 (15)	C35—C44	1.526 (16)
C49—H49	0.9800	C35—H35	0.9800
C40—C39	1.530 (15)	C58—H58A	0.9600
C40—H40	0.9800	C58—H58B	0.9600
C53—C56	1.534 (15)	C58—H58C	0.9600
C53—C52	1.534 (15)	C2—H2A	0.9700
C53—H53	0.9800	C2—H2B	0.9700
C50—C51	1.525 (15)	C28—H28A	0.9600
C50—C59	1.527 (16)	C28—H28B	0.9600
C50—H50	0.9800	C28—H28C	0.9600
C19—C18	1.526 (16)	C21—H21A	0.9700
C19—C20	1.541 (15)	C21—H21B	0.9700
C19—H19	0.9800	C15—H15A	0.9600
C32—C33	1.523 (15)	C15—H15B	0.9600
C32—C31	1.538 (15)	C15—H15C	0.9600
C32—H32A	0.9700	C44—H44A	0.9600
C32—H32B	0.9700	C44—H44B	0.9600
C4—C5	1.542 (15)	C44—H44C	0.9600
C4—H4	0.9800	C36—H36A	0.9700
C27—C26	1.514 (15)	C36—H36B	0.9700
C5—C14	1.518 (15)	C43—C41	1.527 (16)
C5—C6	1.524 (16)	C43—H43A	0.9600
C5—H5	0.9800	C43—H43B	0.9600
C11—C13	1.528 (16)	C43—H43C	0.9600
C11—H11	0.9800	C29—H29A	0.9600
C17—C18	1.529 (15)	C29—H29B	0.9600
C17—H17A	0.9700	C29—H29C	0.9600
C17—H17B	0.9700	C41—H41	0.9800

C27—O9—C25	118 (3)	C8—C7—H7B	110.0
C25—O8—C16	117 (3)	H7A—C7—H7B	108.4
C31—O13—O14	106 (3)	O16—C57—O17	124 (3)
C16—O7—O6	110 (3)	O16—C57—C56	122 (4)
O19—O20—C54	107 (2)	O17—C57—C56	113 (4)
C42—O12—C40	124 (3)	C46—C47—C48	110 (4)
C9—O1—O2	109 (2)	C46—C47—H47A	109.7
C39—O14—O13	112 (2)	C48—C47—H47A	109.7
C40—O15—C31	113 (3)	C46—C47—H47B	109.7
C55—O18—C46	115 (3)	C48—C47—H47B	109.7
C1—O2—O1	113 (3)	H47A—C47—H47B	108.2
C46—O19—O20	110 (3)	C37—C38—C41	113 (4)
C24—O6—O7	112 (2)	C37—C38—C39	116 (4)
C10—O3—C1	109 (3)	C41—C38—C39	109 (3)
C57—O17—C55	124 (3)	C37—C38—H38	105.8
C12—O4—C10	124 (3)	C41—C38—H38	105.8
O7—C16—O8	106 (2)	C39—C38—H38	105.8
O7—C16—C30	103 (3)	C27—C26—C28	113 (4)
O8—C16—C30	108 (3)	C27—C26—C23	108 (3)
O7—C16—C17	111 (3)	C28—C26—C23	116 (4)
O8—C16—C17	110 (3)	C27—C26—H26	106.5
C30—C16—C17	118 (3)	C28—C26—H26	106.5
O1—C9—C10	110 (2)	C23—C26—H26	106.5
O1—C9—C8	101 (3)	C57—C56—C58	108 (4)
C10—C9—C8	113 (3)	C57—C56—C53	110 (4)
O1—C9—C4	109 (3)	C58—C56—C53	109 (4)
C10—C9—C4	111 (3)	C57—C56—H56	109.8
C8—C9—C4	114 (3)	C58—C56—H56	109.8
O20—C54—C53	101 (3)	C53—C56—H56	109.8
O20—C54—C55	114 (3)	C21—C22—C23	107 (3)
C53—C54—C55	103 (3)	C21—C22—H22A	110.2
O20—C54—C49	116 (4)	C23—C22—H22A	110.2
C53—C54—C49	109 (3)	C21—C22—H22B	110.2
C55—C54—C49	113 (4)	C23—C22—H22B	110.2
O3—C10—O4	110 (3)	H22A—C22—H22B	108.5
O3—C10—C9	117 (3)	C51—C52—C53	110 (4)
O4—C10—C9	114 (3)	C51—C52—H52A	109.7
O3—C10—H10	105.1	C53—C52—H52A	109.7
O4—C10—H10	105.1	C51—C52—H52B	109.7
C9—C10—H10	105.1	C53—C52—H52B	109.7
O6—C24—C25	111 (2)	H52A—C52—H52B	108.2
O6—C24—C23	107 (3)	O11—C42—O12	123 (3)
C25—C24—C23	113 (3)	O11—C42—C41	124 (4)
O6—C24—C19	105 (3)	O12—C42—C41	112 (4)
C25—C24—C19	109 (3)	C5—C6—C7	116 (4)
C23—C24—C19	112 (3)	C5—C6—H6A	108.4
O19—C46—O18	105 (3)	C7—C6—H6A	108.4
O19—C46—C60	104 (4)	C5—C6—H6B	108.4
O18—C46—C60	104 (2)	C7—C6—H6B	108.4
O19—C46—C47	116 (3)	H6A—C6—H6B	107.5
O18—C46—C47	114 (3)	C33—C34—C35	114 (4)
C60—C46—C47	112 (3)	C33—C34—C39	112 (3)
O8—C25—O9	106 (3)	C35—C34—C39	106 (4)
O8—C25—C24	113 (3)	C33—C34—H34	108.2
O9—C25—C24	112 (3)	C35—C34—H34	108.2
O8—C25—H25	108.5	C39—C34—H34	108.2
O9—C25—H25	108.5	C19—C18—C17	122 (4)
C24—C25—H25	108.5	C19—C18—H18A	107.0
O18—C55—O17	103 (4)	C17—C18—H18A	107.0
O18—C55—C54	108 (3)	C19—C18—H18B	107.0
O17—C55—C54	115 (4)	C17—C18—H18B	107.0
O18—C55—H55	110.0	H18A—C18—H18B	106.7
O17—C55—H55	110.0	C36—C37—C38	107 (5)
C54—C55—H55	110.0	C36—C37—H37A	110.3
O5—C12—O4	119 (3)	C38—C37—H37A	110.3
O5—C12—C11	118 (3)	C36—C37—H37B	110.3
O4—C12—C11	123 (4)	C38—C37—H37B	110.3
O2—C1—O3	110 (3)	H37A—C37—H37B	108.5
O2—C1—C15	106 (3)	C5—C14—H14A	109.5
O3—C1—C15	106 (3)	C5—C14—H14B	109.5
O2—C1—C2	112 (3)	H14A—C14—H14B	109.5
O3—C1—C2	110 (3)	C5—C14—H14C	109.5
C15—C1—C2	112 (3)	H14A—C14—H14C	109.5
C7—C8—C9	110 (3)	H14B—C14—H14C	109.5
C7—C8—C11	113 (3)	C21—C20—C29	115 (4)
C9—C8—C11	112 (3)	C21—C20—C19	106 (4)
C7—C8—H8	106.9	C29—C20—C19	115 (4)
C9—C8—H8	106.9	C21—C20—H20	106.6
C11—C8—H8	106.9	C29—C20—H20	106.6
C4—C3—C2	120 (4)	C19—C20—H20	106.6
C4—C3—H3A	107.3	C46—C60—H60A	109.5
C2—C3—H3A	107.3	C46—C60—H60B	109.5
C4—C3—H3B	107.3	H60A—C60—H60B	109.5
C2—C3—H3B	107.3	C46—C60—H60C	109.5
H3A—C3—H3B	106.9	H60A—C60—H60C	109.5
C49—C48—C47	123 (5)	H60B—C60—H60C	109.5
C49—C48—H48A	106.6	C16—C30—H30A	109.5
C47—C48—H48A	106.6	C16—C30—H30B	109.5
C49—C48—H48B	106.6	H30A—C30—H30B	109.5
C47—C48—H48B	106.6	C16—C30—H30C	109.5
H48A—C48—H48B	106.6	H30A—C30—H30C	109.5
C48—C49—C54	105 (3)	H30B—C30—H30C	109.5
C48—C49—C50	107 (4)	C52—C51—C50	120 (3)
C54—C49—C50	123 (4)	C52—C51—H51A	107.3
C48—C49—H49	106.9	C50—C51—H51A	107.3
C54—C49—H49	106.9	C52—C51—H51B	107.3
C50—C49—H49	106.9	C50—C51—H51B	107.3
O15—C40—O12	106 (3)	H51A—C51—H51B	106.9
O15—C40—C39	111 (3)	C50—C59—H59A	109.5
O12—C40—C39	117 (4)	C50—C59—H59B	109.5
O15—C40—H40	107.4	H59A—C59—H59B	109.5
O12—C40—H40	107.4	C50—C59—H59C	109.5
C39—C40—H40	107.4	H59A—C59—H59C	109.5
C54—C53—C56	109 (3)	H59B—C59—H59C	109.5
C54—C53—C52	112 (4)	C36—C35—C44	110 (3)
C56—C53—C52	122 (5)	C36—C35—C34	117 (5)
C54—C53—H53	103.9	C44—C35—C34	107 (4)
C56—C53—H53	103.9	C36—C35—H35	107.5
C52—C53—H53	103.9	C44—C35—H35	107.5
C51—C50—C59	116 (4)	C34—C35—H35	107.5
C51—C50—C49	99 (4)	C56—C58—H58A	109.5
C59—C50—C49	120 (5)	C56—C58—H58B	109.5
C51—C50—H50	107.3	H58A—C58—H58B	109.5
C59—C50—H50	107.3	C56—C58—H58C	109.5
C49—C50—H50	107.3	H58A—C58—H58C	109.5
C18—C19—C24	114 (4)	H58B—C58—H58C	109.5
C18—C19—C20	109 (4)	C1—C2—C3	113 (4)
C24—C19—C20	114 (3)	C1—C2—H2A	108.9
C18—C19—H19	106.4	C3—C2—H2A	108.9
C24—C19—H19	106.4	C1—C2—H2B	108.9
C20—C19—H19	106.4	C3—C2—H2B	108.9
C33—C32—C31	118 (3)	H2A—C2—H2B	107.7
C33—C32—H32A	107.9	C26—C28—H28A	109.5
C31—C32—H32A	107.9	C26—C28—H28B	109.5
C33—C32—H32B	107.9	H28A—C28—H28B	109.5
C31—C32—H32B	107.9	C26—C28—H28C	109.5
H32A—C32—H32B	107.2	H28A—C28—H28C	109.5
C3—C4—C9	113 (3)	H28B—C28—H28C	109.5
C3—C4—C5	113 (3)	C22—C21—C20	120 (4)
C9—C4—C5	114 (3)	C22—C21—H21A	107.4
C3—C4—H4	105.5	C20—C21—H21A	107.4
C9—C4—H4	105.5	C22—C21—H21B	107.4
C5—C4—H4	105.5	C20—C21—H21B	107.4
O10—C27—O9	116 (3)	H21A—C21—H21B	106.9
O10—C27—C26	119 (3)	C1—C15—H15A	109.5
O9—C27—C26	122 (4)	C1—C15—H15B	109.5
C14—C5—C6	112 (3)	H15A—C15—H15B	109.5
C14—C5—C4	111 (3)	C1—C15—H15C	109.5
C6—C5—C4	109 (4)	H15A—C15—H15C	109.5
C14—C5—H5	108.3	H15B—C15—H15C	109.5
C6—C5—H5	108.3	C35—C44—H44A	109.5
C4—C5—H5	108.3	C35—C44—H44B	109.5
C12—C11—C13	116 (4)	H44A—C44—H44B	109.5
C12—C11—C8	109 (3)	C35—C44—H44C	109.5
C13—C11—C8	114 (4)	H44A—C44—H44C	109.5
C12—C11—H11	105.8	H44B—C44—H44C	109.5
C13—C11—H11	105.8	C37—C36—C35	113 (4)
C8—C11—H11	105.8	C37—C36—H36A	108.9
C18—C17—C16	113 (3)	C35—C36—H36A	108.9
C18—C17—H17A	108.9	C37—C36—H36B	108.9
C16—C17—H17A	108.9	C35—C36—H36B	108.9
C18—C17—H17B	108.9	H36A—C36—H36B	107.8
C16—C17—H17B	108.9	C41—C43—H43A	109.5
H17A—C17—H17B	107.7	C41—C43—H43B	109.5
C22—C23—C24	111 (3)	H43A—C43—H43B	109.5
C22—C23—C26	112 (3)	C41—C43—H43C	109.5
C24—C23—C26	109 (4)	H43A—C43—H43C	109.5
C22—C23—H23	108.4	H43B—C43—H43C	109.5
C24—C23—H23	108.4	C20—C29—H29A	109.5
C26—C23—H23	108.4	C20—C29—H29B	109.5
C32—C33—C34	115 (4)	H29A—C29—H29B	109.5
C32—C33—H33A	108.6	C20—C29—H29C	109.5
C34—C33—H33A	108.6	H29A—C29—H29C	109.5
C32—C33—H33B	108.6	H29B—C29—H29C	109.5
C34—C33—H33B	108.6	O14—C39—C40	110 (2)
H33A—C33—H33B	107.6	O14—C39—C34	111 (4)
C31—C45—H45A	109.5	C40—C39—C34	114 (3)
C31—C45—H45B	109.5	O14—C39—C38	104 (4)
H45A—C45—H45B	109.5	C40—C39—C38	104 (3)
C31—C45—H45C	109.5	C34—C39—C38	114 (3)
H45A—C45—H45C	109.5	C42—C41—C43	103 (4)
H45B—C45—H45C	109.5	C42—C41—C38	112 (4)
C11—C13—H13A	109.5	C43—C41—C38	111 (3)
C11—C13—H13B	109.5	C42—C41—H41	109.9
H13A—C13—H13B	109.5	C43—C41—H41	109.9
C11—C13—H13C	109.5	C38—C41—H41	109.9
H13A—C13—H13C	109.5	O13—C31—O15	109 (3)
H13B—C13—H13C	109.5	O13—C31—C45	99 (4)
C6—C7—C8	108 (3)	O15—C31—C45	106 (3)
C6—C7—H7A	110.0	O13—C31—C32	113 (3)
C8—C7—H7A	110.0	O15—C31—C32	110 (3)
C6—C7—H7B	110.0	C45—C31—C32	120 (4)

C31—O13—O14—C39	43 (5)	O4—C12—C11—C8	32 (5)
C9—O1—O2—C1	42 (3)	C7—C8—C11—C12	78 (4)
C54—O20—O19—C46	40 (4)	C9—C8—C11—C12	−48 (4)
C16—O7—O6—C24	47 (4)	C7—C8—C11—C13	−53 (4)
O6—O7—C16—O8	−71 (3)	C9—C8—C11—C13	−179 (3)
O6—O7—C16—C30	176 (2)	O7—C16—C17—C18	−90 (3)
O6—O7—C16—C17	49 (3)	O8—C16—C17—C18	27 (4)
C25—O8—C16—O7	32 (4)	C30—C16—C17—C18	152 (4)
C25—O8—C16—C30	142 (3)	O6—C24—C23—C22	172 (3)
C25—O8—C16—C17	−88 (4)	C25—C24—C23—C22	−66 (4)
O2—O1—C9—C10	18 (4)	C19—C24—C23—C22	57 (3)
O2—O1—C9—C8	137 (3)	O6—C24—C23—C26	−65 (3)
O2—O1—C9—C4	−104 (3)	C25—C24—C23—C26	57 (3)
O19—O20—C54—C53	135 (3)	C19—C24—C23—C26	−179 (2)
O19—O20—C54—C55	25 (7)	C31—C32—C33—C34	54 (4)
O19—O20—C54—C49	−108 (4)	C9—C8—C7—C6	−56 (4)
C1—O3—C10—O4	−101 (3)	C11—C8—C7—C6	177 (3)
C1—O3—C10—C9	31 (4)	C55—O17—C57—O16	158 (4)
C12—O4—C10—O3	156 (3)	C55—O17—C57—C56	−34 (6)
C12—O4—C10—C9	23 (5)	O19—C46—C47—C48	−94 (4)
O1—C9—C10—O3	−58 (5)	O18—C46—C47—C48	29 (5)
C8—C9—C10—O3	−170 (3)	C60—C46—C47—C48	147 (4)
C4—C9—C10—O3	62 (4)	C49—C48—C47—C46	55 (4)
O1—C9—C10—O4	72 (4)	O10—C27—C26—C28	−26 (5)
C8—C9—C10—O4	−40 (3)	O9—C27—C26—C28	174 (4)
C4—C9—C10—O4	−168 (3)	O10—C27—C26—C23	−155 (4)
O7—O6—C24—C25	12 (5)	O9—C27—C26—C23	44 (5)
O7—O6—C24—C23	135 (3)	C22—C23—C26—C27	72 (5)
O7—O6—C24—C19	−106 (4)	C24—C23—C26—C27	−51 (4)
O20—O19—C46—O18	−78 (3)	C22—C23—C26—C28	−56 (5)
O20—O19—C46—C60	174 (3)	C24—C23—C26—C28	−179 (3)
O20—O19—C46—C47	49 (3)	O16—C57—C56—C58	−28 (6)
C55—O18—C46—O19	41 (4)	O17—C57—C56—C58	164 (4)
C55—O18—C46—C60	151 (4)	O16—C57—C56—C53	−147 (5)
C55—O18—C46—C47	−87 (4)	O17—C57—C56—C53	44 (5)
C16—O8—C25—O9	−97 (3)	C54—C53—C56—C57	−64 (4)
C16—O8—C25—C24	26 (4)	C52—C53—C56—C57	70 (4)
C27—O9—C25—O8	162 (3)	C54—C53—C56—C58	178 (2)
C27—O9—C25—C24	38 (4)	C52—C53—C56—C58	−49 (4)
O6—C24—C25—O8	−49 (5)	C24—C23—C22—C21	−54 (4)
C23—C24—C25—O8	−168 (3)	C26—C23—C22—C21	−176 (4)
C19—C24—C25—O8	67 (3)	C54—C53—C52—C51	−50 (3)
O6—C24—C25—O9	71 (4)	C56—C53—C52—C51	178 (3)
C23—C24—C25—O9	−49 (4)	C40—O12—C42—O11	157 (4)
C19—C24—C25—O9	−174 (3)	C40—O12—C42—C41	−34 (6)
C46—O18—C55—O17	−101 (4)	C14—C5—C6—C7	−178 (2)
C46—O18—C55—C54	21 (5)	C4—C5—C6—C7	−55 (4)
C57—O17—C55—O18	157 (4)	C8—C7—C6—C5	60 (4)
C57—O17—C55—C54	40 (6)	C32—C33—C34—C35	−152 (4)
O20—C54—C55—O18	−58 (7)	C32—C33—C34—C39	−32 (4)
C53—C54—C55—O18	−166 (3)	C24—C19—C18—C17	−29 (5)
C49—C54—C55—O18	77 (4)	C20—C19—C18—C17	−158 (3)
O20—C54—C55—O17	56 (6)	C16—C17—C18—C19	50 (5)
C53—C54—C55—O17	−51 (4)	C41—C38—C37—C36	−178 (3)
C49—C54—C55—O17	−169 (3)	C39—C38—C37—C36	−51 (4)
C10—O4—C12—O5	162 (3)	C18—C19—C20—C21	178 (4)
C10—O4—C12—C11	−21 (6)	C24—C19—C20—C21	50 (5)
O1—O2—C1—O3	−73 (3)	C18—C19—C20—C29	−53 (5)
O1—O2—C1—C15	173 (3)	C24—C19—C20—C29	178 (4)
O1—O2—C1—C2	50 (3)	C53—C52—C51—C50	60 (4)
C10—O3—C1—O2	31 (4)	C59—C50—C51—C52	176 (3)
C10—O3—C1—C15	145 (3)	C49—C50—C51—C52	−55 (4)
C10—O3—C1—C2	−93 (4)	C33—C34—C35—C36	178 (3)
O1—C9—C8—C7	170 (2)	C39—C34—C35—C36	54 (4)
C10—C9—C8—C7	−73 (3)	C33—C34—C35—C44	−58 (4)
C4—C9—C8—C7	54 (3)	C39—C34—C35—C44	178 (3)
O1—C9—C8—C11	−63 (3)	O2—C1—C2—C3	−91 (4)
C10—C9—C8—C11	54 (3)	O3—C1—C2—C3	32 (5)
C4—C9—C8—C11	−178.7 (19)	C15—C1—C2—C3	150 (4)
C47—C48—C49—C54	−34 (4)	C4—C3—C2—C1	51 (5)
C47—C48—C49—C50	−167 (4)	C23—C22—C21—C20	56 (4)
O20—C54—C49—C48	72 (4)	C29—C20—C21—C22	179 (3)
C53—C54—C49—C48	−175 (2)	C19—C20—C21—C22	−53 (5)
C55—C54—C49—C48	−62 (4)	C38—C37—C36—C35	51 (4)
O20—C54—C49—C50	−166 (5)	C44—C35—C36—C37	−180 (3)
C53—C54—C49—C50	−53 (4)	C34—C35—C36—C37	−58 (5)
C55—C54—C49—C50	61 (5)	O13—O14—C39—C40	20 (7)
C31—O15—C40—O12	−99 (3)	O13—O14—C39—C34	−107 (4)
C31—O15—C40—C39	30 (4)	O13—O14—C39—C38	131 (4)
C42—O12—C40—O15	162 (4)	O15—C40—C39—O14	−59 (6)
C42—O12—C40—C39	37 (5)	O12—C40—C39—O14	63 (6)
O20—C54—C53—C56	−53 (3)	O15—C40—C39—C34	67 (4)
C55—C54—C53—C56	64 (3)	O12—C40—C39—C34	−172 (3)
C49—C54—C53—C56	−176 (2)	O15—C40—C39—C38	−169 (3)
O20—C54—C53—C52	169 (3)	O12—C40—C39—C38	−47 (4)
C55—C54—C53—C52	−74 (3)	C33—C34—C39—O14	68 (4)
C49—C54—C53—C52	46 (3)	C35—C34—C39—O14	−167 (4)
C48—C49—C50—C51	174 (3)	C33—C34—C39—C40	−56 (4)
C54—C49—C50—C51	53 (4)	C35—C34—C39—C40	69 (4)
C48—C49—C50—C59	−60 (4)	C33—C34—C39—C38	−175 (3)
C54—C49—C50—C59	179 (4)	C35—C34—C39—C38	−50 (3)
O6—C24—C19—C18	63 (4)	C37—C38—C39—O14	175 (4)
C25—C24—C19—C18	−57 (4)	C41—C38—C39—O14	−56 (3)
C23—C24—C19—C18	178 (3)	C37—C38—C39—C40	−70 (4)
O6—C24—C19—C20	−171 (4)	C41—C38—C39—C40	59 (3)
C25—C24—C19—C20	70 (5)	C37—C38—C39—C34	54 (4)
C23—C24—C19—C20	−56 (4)	C41—C38—C39—C34	−176 (2)
C2—C3—C4—C9	−31 (5)	O11—C42—C41—C43	−25 (6)
C2—C3—C4—C5	−162 (3)	O12—C42—C41—C43	166 (4)
O1—C9—C4—C3	68 (4)	O11—C42—C41—C38	−145 (4)
C10—C9—C4—C3	−53 (3)	O12—C42—C41—C38	46 (5)
C8—C9—C4—C3	179 (3)	C37—C38—C41—C42	69 (4)
O1—C9—C4—C5	−162 (3)	C39—C38—C41—C42	−62 (4)
C10—C9—C4—C5	77 (4)	C37—C38—C41—C43	−46 (4)
C8—C9—C4—C5	−50 (4)	C39—C38—C41—C43	−177 (3)
C25—O9—C27—O10	161 (3)	O14—O13—C31—O15	−74 (3)
C25—O9—C27—C26	−38 (5)	O14—O13—C31—C45	175 (3)
C3—C4—C5—C14	−58 (5)	O14—O13—C31—C32	48 (3)
C9—C4—C5—C14	172 (3)	C40—O15—C31—O13	36 (4)
C3—C4—C5—C6	178 (3)	C40—O15—C31—C45	141 (5)
C9—C4—C5—C6	48 (4)	C40—O15—C31—C32	−89 (4)
O5—C12—C11—C13	−20 (6)	C33—C32—C31—O13	−97 (4)
O4—C12—C11—C13	162 (4)	C33—C32—C31—O15	25 (5)
O5—C12—C11—C8	−150 (4)	C33—C32—C31—C45	147 (4)

(FormII_6) top

Crystal data top

C₁₅H₂₂O₅	Z = 4
M_r = 282.32	F(000) = 608
Triclinic, P1	D_x = 1.439 Mg m⁻³
a = 9.542 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.616 (8) Å	Cell parameters from 2249 reflections
c = 9.628 (12) Å	θ = 2.2–23.2°
α = 88.97 (8)°	µ = 0.11 mm⁻¹
β = 103.94 (8)°	T = 296 K
γ = 89.81 (3)°	Plate, clear colourless
V = 1303 (2) Å³	0.12 × 0.06 × 0.05 mm

Data collection top

Bruker Photon III diffractometer	1462 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	590 reflections with I > 2σ(I)
Mirror optics monochromator	R_int = 0.069
Detector resolution: 7.9 pixels mm^-1	θ_max = 23.2°, θ_min = 2.2°
ω scans	h = −10→10
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1038 before and 0.0623 after correction. The Ratio of minimum to maximum transmission is 0.7369. The λ/2 correction factor is Not present.	k = −16→12
T_min = 0.549, T_max = 0.745	l = −5→5
2249 measured 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)] = 0.108	w = 1/[σ²(F_o²) + (0.1936P)² + 1.2252P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.351	(Δ/σ)_max = 0.002
S = 1.05	Δρ_max = 0.23 e Å⁻³
1462 reflections	Δρ_min = −0.24 e Å⁻³
321 parameters	Absolute structure: Flack x determined using 169 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
95 restraints	Absolute structure parameter: −4.5 (10)

Special details top

Refinement. CX-ASAP (Thompson, 2023)

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

	x	y	z	U_iso*/U_eq
O9	0.333 (4)	0.312 (3)	0.482 (8)	0.047 (11)*
O8	0.298 (4)	0.310 (3)	0.234 (7)	0.062 (14)*
O13	0.476 (5)	0.731 (3)	0.674 (8)	0.077 (15)*
O7	0.518 (5)	0.236 (3)	0.313 (9)	0.099 (17)*
O20	−0.113 (4)	0.560 (2)	0.650 (9)	0.058 (12)*
O12	0.656 (5)	0.819 (3)	0.519 (12)	0.060 (13)*
O1	1.115 (4)	0.068 (3)	0.383 (9)	0.055 (12)*
O14	0.394 (4)	0.812 (2)	0.603 (8)	0.067 (13)*
O15	0.689 (5)	0.806 (4)	0.760 (11)	0.094 (17)*
O18	0.183 (4)	0.520 (3)	0.757 (9)	0.043 (10)*
O2	1.057 (5)	−0.020 (3)	0.320 (8)	0.105 (19)*
O19	−0.051 (5)	0.472 (3)	0.709 (9)	0.078 (15)*
O6	0.602 (4)	0.320 (2)	0.358 (8)	0.069 (14)*
O3	0.808 (4)	0.018 (3)	0.220 (8)	0.059 (13)*
O17	0.139 (5)	0.522 (3)	0.507 (10)	0.080 (16)*
O11	0.623 (6)	0.807 (3)	0.306 (14)	0.081 (17)*
O4	0.855 (4)	0.020 (3)	0.472 (8)	0.074 (15)*
O16	0.096 (5)	0.521 (3)	0.263 (10)	0.091 (18)*
O10	0.357 (5)	0.302 (3)	0.697 (11)	0.091 (16)*
C16	0.410 (6)	0.262 (4)	0.189 (8)	0.06 (2)*
O5	0.892 (4)	0.012 (3)	0.696 (9)	0.050 (12)*
C9	0.990 (4)	0.129 (3)	0.367 (7)	0.047 (19)*
C54	0.009 (4)	0.618 (3)	0.640 (11)	0.050 (19)*
C10	0.853 (5)	0.072 (5)	0.342 (8)	0.07 (2)*
H10	0.774740	0.116699	0.335597	0.083*
C24	0.512 (4)	0.392 (3)	0.393 (8)	0.017 (13)*
C46	0.081 (6)	0.469 (5)	0.814 (8)	0.14 (4)*
C25	0.354 (4)	0.361 (4)	0.357 (7)	0.040 (17)*
H25	0.294942	0.416846	0.348503	0.048*
C55	0.154 (5)	0.576 (4)	0.633 (9)	0.05 (2)*
H55	0.228041	0.622949	0.638573	0.066*
C12	0.919 (5)	0.056 (4)	0.598 (8)	0.04 (2)*
C1	0.941 (5)	−0.015 (4)	0.196 (8)	0.08 (3)*
C8	1.050 (5)	0.163 (4)	0.520 (7)	0.036 (17)*
H8	1.147138	0.185829	0.522904	0.044*
C3	0.930 (5)	0.150 (3)	0.107 (8)	0.051 (19)*
H3A	0.958257	0.187071	0.033567	0.062*
H3B	0.825594	0.150822	0.084162	0.062*
C48	0.073 (6)	0.631 (3)	0.899 (11)	0.06 (2)*
H48A	0.042694	0.664382	0.972072	0.073*
H48B	0.177800	0.633232	0.922122	0.073*
C49	0.023 (5)	0.688 (3)	0.761 (10)	0.045 (16)*
H49	−0.074849	0.709645	0.758798	0.054*
C40	0.647 (5)	0.869 (5)	0.645 (11)	0.08 (3)*
H40	0.706827	0.924057	0.657012	0.093*
C53	−0.031 (5)	0.666 (4)	0.493 (11)	0.045 (17)*
H53	−0.126161	0.690954	0.492395	0.054*
C50	0.115 (7)	0.773 (4)	0.753 (12)	0.08 (2)*
H50	0.213723	0.752047	0.755391	0.098*
C19	0.519 (6)	0.453 (4)	0.264 (8)	0.05 (2)*
H19	0.622673	0.465558	0.278450	0.060*
C32	0.533 (7)	0.818 (4)	0.902 (12)	0.09 (3)*
H32A	0.429471	0.811423	0.882557	0.109*
H32B	0.571232	0.791971	0.996868	0.109*
C4	0.980 (5)	0.201 (3)	0.247 (7)	0.033 (16)*
H4	1.078277	0.223080	0.251549	0.040*
C27	0.404 (8)	0.344 (6)	0.609 (8)	0.15 (5)*
C5	0.886 (6)	0.284 (3)	0.266 (10)	0.05 (2)*
H5	0.787178	0.262320	0.254256	0.060*
C11	1.067 (4)	0.099 (4)	0.651 (8)	0.029 (15)*
H11	1.139273	0.052088	0.645910	0.035*
C17	0.464 (6)	0.324 (3)	0.083 (11)	0.058 (19)*
H17A	0.559818	0.301973	0.079955	0.069*
H17B	0.401853	0.314098	−0.011396	0.069*
C23	0.592 (6)	0.442 (3)	0.529 (7)	0.08 (2)*
H23	0.694759	0.452971	0.534749	0.097*
C33	0.558 (7)	0.921 (4)	0.920 (9)	0.09 (2)*
H33A	0.512554	0.946102	0.990510	0.102*
H33B	0.660216	0.936119	0.943559	0.102*
C45	0.663 (10)	0.664 (6)	0.85 (2)	0.16 (4)*
H45A	0.735084	0.675815	0.940546	0.244*
H45B	0.597518	0.618508	0.873841	0.244*
H45C	0.708883	0.642096	0.782766	0.244*
C13	1.117 (9)	0.147 (6)	0.794 (9)	0.14 (4)*
H13A	1.213964	0.167961	0.804040	0.207*
H13B	1.054459	0.198184	0.796399	0.207*
H13C	1.113852	0.104949	0.870993	0.207*
C7	0.963 (8)	0.247 (4)	0.547 (10)	0.12 (3)*
H7A	0.869634	0.227603	0.560356	0.139*
H7B	1.013919	0.276904	0.633878	0.139*
C57	0.061 (7)	0.537 (5)	0.373 (10)	0.07 (3)*
C47	0.037 (6)	0.530 (3)	0.923 (13)	0.06 (2)*
H47A	0.086844	0.510171	1.018576	0.072*
H47B	−0.066235	0.524505	0.914633	0.072*
C38	0.442 (8)	0.932 (6)	0.489 (9)	0.11 (3)*
H38	0.339260	0.940881	0.484613	0.128*
C26	0.563 (8)	0.365 (6)	0.629 (13)	0.10 (4)*
H26	0.614615	0.308903	0.615486	0.120*
C56	−0.073 (7)	0.591 (5)	0.380 (12)	0.08 (3)*
H56	−0.148254	0.551342	0.400796	0.101*
C22	0.502 (6)	0.527 (3)	0.539 (12)	0.06 (2)*
H22A	0.400790	0.511662	0.521151	0.076*
H22B	0.532276	0.552879	0.633312	0.076*
C52	0.054 (7)	0.755 (4)	0.488 (14)	0.10 (3)*
H52A	0.152868	0.739280	0.489419	0.124*
H52B	0.013025	0.786649	0.397428	0.124*
C42	0.592 (7)	0.858 (9)	0.391 (10)	0.40 (17)*
C6	0.942 (6)	0.314 (4)	0.420 (10)	0.047 (19)*
H6A	1.034538	0.342361	0.425923	0.057*
H6B	0.876792	0.361143	0.435948	0.057*
C34	0.483 (7)	0.952 (4)	0.768 (9)	0.052 (19)*
H34	0.380348	0.960241	0.765930	0.062*
C18	0.474 (8)	0.427 (4)	0.106 (9)	0.10 (3)*
H18A	0.542666	0.451910	0.056888	0.120*
H18B	0.380454	0.454127	0.063958	0.120*
C37	0.477 (11)	1.030 (6)	0.448 (15)	0.16 (5)*
H37A	0.564994	1.028740	0.414301	0.197*
H37B	0.399648	1.052348	0.369967	0.197*
C14	0.886 (6)	0.357 (4)	0.152 (10)	0.07 (2)*
H14A	0.849277	0.332183	0.058517	0.099*
H14B	0.825050	0.407357	0.164674	0.099*
H14C	0.982249	0.378768	0.159778	0.099*
C20	0.454 (6)	0.546 (3)	0.290 (11)	0.053 (18)*
H20	0.352256	0.536875	0.288367	0.063*
C60	0.115 (8)	0.385 (6)	0.908 (14)	0.12 (3)*
H60A	0.206698	0.391651	0.974399	0.184*
H60B	0.041326	0.376490	0.960224	0.184*
H60C	0.117497	0.332210	0.850368	0.184*
C30	0.336 (7)	0.173 (4)	0.143 (15)	0.11 (3)*
H30A	0.259632	0.182949	0.058367	0.164*
H30B	0.403922	0.129431	0.123033	0.164*
H30C	0.295291	0.148493	0.218248	0.164*
C51	0.054 (8)	0.821 (5)	0.609 (12)	0.09 (3)*
H51A	−0.043685	0.842064	0.603989	0.107*
H51B	0.112335	0.873978	0.599581	0.107*
C59	0.123 (6)	0.841 (4)	0.873 (13)	0.07 (2)*
H59A	0.161337	0.810836	0.963393	0.111*
H59B	0.184394	0.890640	0.860397	0.111*
H59C	0.027794	0.863834	0.869215	0.111*
C35	0.534 (8)	1.042 (5)	0.714 (13)	0.09 (3)*
H35	0.635632	1.027562	0.721029	0.111*
C58	−0.118 (9)	0.634 (6)	0.230 (13)	0.11 (3)*
H58A	−0.203726	0.670705	0.222809	0.160*
H58B	−0.042061	0.671816	0.213191	0.160*
H58C	−0.138389	0.586604	0.160729	0.160*
C2	0.974 (6)	0.051 (3)	0.084 (11)	0.056 (19)*
H2A	0.923336	0.032418	−0.010837	0.067*
H2B	1.077019	0.049355	0.088345	0.067*
C28	0.612 (6)	0.394 (4)	0.785 (14)	0.05 (2)*
H28A	0.712688	0.408475	0.806486	0.082*
H28B	0.557512	0.446922	0.799427	0.082*
H28C	0.596073	0.344972	0.847216	0.082*
C21	0.526 (9)	0.596 (5)	0.426 (10)	0.13 (4)*
H21A	0.628056	0.605749	0.432804	0.150*
H21B	0.478951	0.653972	0.432143	0.150*
C15	0.899 (7)	−0.105 (4)	0.122 (12)	0.10 (3)*
H15A	0.820348	−0.094196	0.039531	0.145*
H15B	0.980002	−0.129551	0.091918	0.145*
H15C	0.869804	−0.146807	0.186683	0.145*
C44	0.549 (6)	1.111 (4)	0.834 (14)	0.07 (2)*
H44A	0.572894	1.079194	0.925065	0.104*
H44B	0.624539	1.153492	0.829362	0.104*
H44C	0.459771	1.143806	0.824033	0.104*
C36	0.496 (8)	1.096 (5)	0.572 (13)	0.08 (2)*
H36A	0.572971	1.138537	0.568576	0.096*
H36B	0.407927	1.130476	0.564725	0.096*
C43	0.384 (7)	0.905 (5)	0.213 (13)	0.08 (3)*
H43A	0.280423	0.912626	0.186016	0.127*
H43B	0.428150	0.963831	0.209664	0.127*
H43C	0.413422	0.864767	0.148258	0.127*
C29	0.466 (6)	0.619 (4)	0.178 (12)	0.07 (2)*
H29A	0.423801	0.596324	0.084341	0.110*
H29B	0.415064	0.672859	0.194031	0.110*
H29C	0.565488	0.632805	0.186114	0.110*
C39	0.489 (4)	0.890 (3)	0.641 (9)	0.038 (17)*
C41	0.429 (7)	0.865 (6)	0.365 (12)	0.08 (3)*
H41	0.381769	0.807422	0.379003	0.102*
C31	0.581 (7)	0.751 (4)	0.801 (8)	0.10 (3)*

Geometric parameters (Å, º) top

O9—C27	1.347 (15)	C23—C22	1.532 (14)
O9—C25	1.443 (14)	C23—C26	1.542 (14)
O8—C25	1.406 (14)	C23—H23	0.9800
O8—C16	1.442 (14)	C33—C34	1.528 (15)
O13—C31	1.416 (15)	C33—H33A	0.9700
O13—O14	1.479 (14)	C33—H33B	0.9700
O7—C16	1.420 (14)	C45—C31	1.508 (14)
O7—O6	1.482 (14)	C45—H45A	0.9600
O20—C54	1.463 (14)	C45—H45B	0.9600
O20—O19	1.467 (14)	C45—H45C	0.9600
O12—C42	1.344 (15)	C13—H13A	0.9600
O12—C40	1.442 (15)	C13—H13B	0.9600
O1—C9	1.465 (14)	C13—H13C	0.9600
O1—O2	1.472 (14)	C7—C6	1.525 (15)
O14—C39	1.463 (14)	C7—H7A	0.9700
O15—C40	1.407 (15)	C7—H7B	0.9700
O15—C31	1.441 (14)	C57—C56	1.515 (14)
O18—C55	1.404 (14)	C47—H47A	0.9700
O18—C46	1.435 (14)	C47—H47B	0.9700
O2—C1	1.418 (14)	C38—C37	1.535 (14)
O19—C46	1.411 (15)	C38—C39	1.537 (15)
O6—C24	1.462 (14)	C38—C41	1.541 (15)
O3—C10	1.405 (14)	C38—H38	0.9800
O3—C1	1.437 (14)	C26—C28	1.529 (15)
O17—C57	1.344 (15)	C26—H26	0.9800
O17—C55	1.441 (14)	C56—C58	1.527 (15)
O11—C42	1.208 (15)	C56—H56	0.9800
O4—C12	1.345 (15)	C22—C21	1.524 (15)
O4—C10	1.441 (14)	C22—H22A	0.9700
O16—C57	1.208 (14)	C22—H22B	0.9700
O10—C27	1.210 (15)	C52—C51	1.528 (15)
C16—C30	1.508 (14)	C52—H52A	0.9700
C16—C17	1.534 (14)	C52—H52B	0.9700
O5—C12	1.210 (14)	C42—C41	1.514 (15)
C9—C10	1.531 (14)	C6—H6A	0.9700
C9—C4	1.537 (14)	C6—H6B	0.9700
C9—C8	1.537 (15)	C34—C35	1.534 (14)
C54—C55	1.533 (14)	C34—C39	1.539 (14)
C54—C49	1.535 (14)	C34—H34	0.9800
C54—C53	1.536 (15)	C18—H18A	0.9700
C10—H10	0.9800	C18—H18B	0.9700
C24—C25	1.533 (14)	C37—C36	1.526 (15)
C24—C19	1.536 (14)	C37—H37A	0.9700
C24—C23	1.538 (15)	C37—H37B	0.9700
C46—C60	1.505 (14)	C14—H14A	0.9600
C46—C47	1.524 (15)	C14—H14B	0.9600
C25—H25	0.9800	C14—H14C	0.9600
C55—H55	0.9800	C20—C29	1.525 (15)
C12—C11	1.514 (14)	C20—C21	1.525 (15)
C1—C15	1.508 (14)	C20—H20	0.9800
C1—C2	1.528 (14)	C60—H60A	0.9600
C8—C7	1.538 (14)	C60—H60B	0.9600
C8—C11	1.540 (14)	C60—H60C	0.9600
C8—H8	0.9800	C30—H30A	0.9600
C3—C4	1.527 (15)	C30—H30B	0.9600
C3—C2	1.531 (14)	C30—H30C	0.9600
C3—H3A	0.9700	C51—H51A	0.9700
C3—H3B	0.9700	C51—H51B	0.9700
C48—C49	1.526 (15)	C59—H59A	0.9600
C48—C47	1.538 (14)	C59—H59B	0.9600
C48—H48A	0.9700	C59—H59C	0.9600
C48—H48B	0.9700	C35—C36	1.525 (15)
C49—C50	1.537 (14)	C35—C44	1.526 (15)
C49—H49	0.9800	C35—H35	0.9800
C40—C39	1.534 (14)	C58—H58A	0.9600
C40—H40	0.9800	C58—H58B	0.9600
C53—C52	1.538 (14)	C58—H58C	0.9600
C53—C56	1.539 (15)	C2—H2A	0.9700
C53—H53	0.9800	C2—H2B	0.9700
C50—C59	1.526 (15)	C28—H28A	0.9600
C50—C51	1.528 (15)	C28—H28B	0.9600
C50—H50	0.9800	C28—H28C	0.9600
C19—C18	1.526 (15)	C21—H21A	0.9700
C19—C20	1.539 (14)	C21—H21B	0.9700
C19—H19	0.9800	C15—H15A	0.9600
C32—C33	1.530 (14)	C15—H15B	0.9600
C32—C31	1.532 (14)	C15—H15C	0.9600
C32—H32A	0.9700	C44—H44A	0.9600
C32—H32B	0.9700	C44—H44B	0.9600
C4—C5	1.544 (14)	C44—H44C	0.9600
C4—H4	0.9800	C36—H36A	0.9700
C27—C26	1.514 (14)	C36—H36B	0.9700
C5—C14	1.522 (15)	C43—C41	1.530 (15)
C5—C6	1.526 (15)	C43—H43A	0.9600
C5—H5	0.9800	C43—H43B	0.9600
C11—C13	1.528 (15)	C43—H43C	0.9600
C11—H11	0.9800	C29—H29A	0.9600
C17—C18	1.527 (14)	C29—H29B	0.9600
C17—H17A	0.9700	C29—H29C	0.9600
C17—H17B	0.9700	C41—H41	0.9800

C27—O9—C25	116 (4)	C8—C7—H7B	109.8
C25—O8—C16	111 (5)	H7A—C7—H7B	108.3
C31—O13—O14	114 (6)	O16—C57—O17	127 (6)
C16—O7—O6	105 (5)	O16—C57—C56	124 (7)
C54—O20—O19	106 (4)	O17—C57—C56	108 (7)
C42—O12—C40	117 (5)	C46—C47—C48	111 (7)
C9—O1—O2	106 (4)	C46—C47—H47A	109.5
C39—O14—O13	106 (4)	C48—C47—H47A	109.5
C40—O15—C31	119 (6)	C46—C47—H47B	109.5
C55—O18—C46	127 (5)	C48—C47—H47B	109.5
C1—O2—O1	117 (5)	H47A—C47—H47B	108.1
C46—O19—O20	120 (5)	C37—C38—C39	125 (8)
C24—O6—O7	112 (3)	C37—C38—C41	113 (8)
C10—O3—C1	103 (6)	C39—C38—C41	116 (7)
C57—O17—C55	130 (5)	C37—C38—H38	98.6
C12—O4—C10	119 (5)	C39—C38—H38	98.6
O7—C16—O8	108 (4)	C41—C38—H38	98.6
O7—C16—C30	103 (6)	C27—C26—C28	104 (7)
O8—C16—C30	101 (5)	C27—C26—C23	114 (7)
O7—C16—C17	114 (6)	C28—C26—C23	110 (8)
O8—C16—C17	108 (5)	C27—C26—H26	109.7
C30—C16—C17	121 (6)	C28—C26—H26	109.7
O1—C9—C10	109 (4)	C23—C26—H26	109.7
O1—C9—C4	113 (4)	C57—C56—C58	102 (6)
C10—C9—C4	111 (5)	C57—C56—C53	109 (6)
O1—C9—C8	91 (4)	C58—C56—C53	110 (7)
C10—C9—C8	116 (5)	C57—C56—H56	111.5
C4—C9—C8	116 (5)	C58—C56—H56	111.5
O20—C54—C55	121 (4)	C53—C56—H56	111.5
O20—C54—C49	106 (5)	C21—C22—C23	107 (6)
C55—C54—C49	113 (5)	C21—C22—H22A	110.2
O20—C54—C53	107 (6)	C23—C22—H22A	110.2
C55—C54—C53	99 (5)	C21—C22—H22B	110.2
C49—C54—C53	111 (4)	C23—C22—H22B	110.2
O3—C10—O4	112 (5)	H22A—C22—H22B	108.5
O3—C10—C9	122 (5)	C51—C52—C53	115 (8)
O4—C10—C9	108 (5)	C51—C52—H52A	108.4
O3—C10—H10	104.5	C53—C52—H52A	108.4
O4—C10—H10	104.5	C51—C52—H52B	108.4
C9—C10—H10	104.5	C53—C52—H52B	108.4
O6—C24—C25	109 (3)	H52A—C52—H52B	107.5
O6—C24—C19	94 (4)	O11—C42—O12	103 (10)
C25—C24—C19	103 (4)	O11—C42—C41	110 (7)
O6—C24—C23	111 (4)	O12—C42—C41	114 (8)
C25—C24—C23	127 (5)	C7—C6—C5	123 (6)
C19—C24—C23	108 (4)	C7—C6—H6A	106.6
O19—C46—O18	107 (4)	C5—C6—H6A	106.7
O19—C46—C60	118 (6)	C7—C6—H6B	106.6
O18—C46—C60	125 (6)	C5—C6—H6B	106.6
O19—C46—C47	98 (7)	H6A—C6—H6B	106.6
O18—C46—C47	107 (6)	C33—C34—C35	116 (7)
C60—C46—C47	97 (5)	C33—C34—C39	120 (5)
O8—C25—O9	109 (5)	C35—C34—C39	100 (6)
O8—C25—C24	121 (5)	C33—C34—H34	106.7
O9—C25—C24	106 (4)	C35—C34—H34	106.7
O8—C25—H25	106.4	C39—C34—H34	106.7
O9—C25—H25	106.4	C19—C18—C17	114 (7)
C24—C25—H25	106.4	C19—C18—H18A	108.7
O18—C55—O17	110 (6)	C17—C18—H18A	108.7
O18—C55—C54	101 (5)	C19—C18—H18B	108.7
O17—C55—C54	111 (6)	C17—C18—H18B	108.7
O18—C55—H55	111.4	H18A—C18—H18B	107.6
O17—C55—H55	111.4	C36—C37—C38	113 (9)
C54—C55—H55	111.4	C36—C37—H37A	109.0
O5—C12—O4	111 (5)	C38—C37—H37A	109.0
O5—C12—C11	108 (4)	C36—C37—H37B	109.0
O4—C12—C11	131 (5)	C38—C37—H37B	109.0
O2—C1—O3	114 (5)	H37A—C37—H37B	107.8
O2—C1—C15	116 (6)	C5—C14—H14A	109.5
O3—C1—C15	103 (5)	C5—C14—H14B	109.5
O2—C1—C2	111 (6)	H14A—C14—H14B	109.5
O3—C1—C2	104 (5)	C5—C14—H14C	109.5
C15—C1—C2	107 (5)	H14A—C14—H14C	109.5
C9—C8—C7	110 (6)	H14B—C14—H14C	109.5
C9—C8—C11	121 (5)	C29—C20—C21	100 (5)
C7—C8—C11	107 (5)	C29—C20—C19	113 (5)
C9—C8—H8	105.8	C21—C20—C19	118 (6)
C7—C8—H8	105.8	C29—C20—H20	108.6
C11—C8—H8	105.8	C21—C20—H20	108.6
C4—C3—C2	124 (6)	C19—C20—H20	108.6
C4—C3—H3A	106.2	C46—C60—H60A	109.5
C2—C3—H3A	106.2	C46—C60—H60B	109.5
C4—C3—H3B	106.2	H60A—C60—H60B	109.5
C2—C3—H3B	106.2	C46—C60—H60C	109.5
H3A—C3—H3B	106.4	H60A—C60—H60C	109.5
C49—C48—C47	127 (7)	H60B—C60—H60C	109.5
C49—C48—H48A	105.6	C16—C30—H30A	109.5
C47—C48—H48A	105.6	C16—C30—H30B	109.5
C49—C48—H48B	105.6	H30A—C30—H30B	109.5
C47—C48—H48B	105.6	C16—C30—H30C	109.5
H48A—C48—H48B	106.1	H30A—C30—H30C	109.5
C48—C49—C54	105 (5)	H30B—C30—H30C	109.5
C48—C49—C50	114 (6)	C52—C51—C50	110 (6)
C54—C49—C50	117 (6)	C52—C51—H51A	109.8
C48—C49—H49	106.9	C50—C51—H51A	109.8
C54—C49—H49	106.9	C52—C51—H51B	109.8
C50—C49—H49	106.9	C50—C51—H51B	109.8
O15—C40—O12	106 (6)	H51A—C51—H51B	108.2
O15—C40—C39	104 (5)	C50—C59—H59A	109.5
O12—C40—C39	110 (6)	C50—C59—H59B	109.5
O15—C40—H40	112.3	H59A—C59—H59B	109.5
O12—C40—H40	112.3	C50—C59—H59C	109.5
C39—C40—H40	112.3	H59A—C59—H59C	109.5
C54—C53—C52	113 (7)	H59B—C59—H59C	109.5
C54—C53—C56	107 (5)	C36—C35—C44	108 (6)
C52—C53—C56	130 (8)	C36—C35—C34	134 (8)
C54—C53—H53	100.4	C44—C35—C34	108 (6)
C52—C53—H53	100.4	C36—C35—H35	100.5
C56—C53—H53	100.4	C44—C35—H35	100.5
C59—C50—C51	109 (6)	C34—C35—H35	100.5
C59—C50—C49	115 (7)	C56—C58—H58A	109.5
C51—C50—C49	108 (7)	C56—C58—H58B	109.5
C59—C50—H50	108.2	H58A—C58—H58B	109.5
C51—C50—H50	108.2	C56—C58—H58C	109.5
C49—C50—H50	108.2	H58A—C58—H58C	109.5
C18—C19—C24	127 (6)	H58B—C58—H58C	109.5
C18—C19—C20	112 (6)	C1—C2—C3	112 (6)
C24—C19—C20	105 (5)	C1—C2—H2A	109.2
C18—C19—H19	103.5	C3—C2—H2A	109.2
C24—C19—H19	103.5	C1—C2—H2B	109.2
C20—C19—H19	103.5	C3—C2—H2B	109.2
C33—C32—C31	131 (6)	H2A—C2—H2B	107.9
C33—C32—H32A	104.6	C26—C28—H28A	109.5
C31—C32—H32A	104.6	C26—C28—H28B	109.5
C33—C32—H32B	104.6	H28A—C28—H28B	109.5
C31—C32—H32B	104.6	C26—C28—H28C	109.5
H32A—C32—H32B	105.7	H28A—C28—H28C	109.5
C3—C4—C9	106 (5)	H28B—C28—H28C	109.5
C3—C4—C5	116 (5)	C22—C21—C20	100 (7)
C9—C4—C5	111 (4)	C22—C21—H21A	111.8
C3—C4—H4	107.7	C20—C21—H21A	111.8
C9—C4—H4	107.7	C22—C21—H21B	111.8
C5—C4—H4	107.7	C20—C21—H21B	111.8
O10—C27—O9	106 (8)	H21A—C21—H21B	109.5
O10—C27—C26	123 (6)	C1—C15—H15A	109.5
O9—C27—C26	117 (8)	C1—C15—H15B	109.5
C14—C5—C6	116 (6)	H15A—C15—H15B	109.5
C14—C5—C4	111 (5)	C1—C15—H15C	109.5
C6—C5—C4	106 (6)	H15A—C15—H15C	109.5
C14—C5—H5	107.9	H15B—C15—H15C	109.5
C6—C5—H5	107.9	C35—C44—H44A	109.5
C4—C5—H5	107.9	C35—C44—H44B	109.5
C12—C11—C13	125 (5)	H44A—C44—H44B	109.5
C12—C11—C8	94 (4)	C35—C44—H44C	109.5
C13—C11—C8	113 (6)	H44A—C44—H44C	109.5
C12—C11—H11	107.8	H44B—C44—H44C	109.5
C13—C11—H11	107.8	C35—C36—C37	110 (7)
C8—C11—H11	107.8	C35—C36—H36A	109.7
C18—C17—C16	119 (6)	C37—C36—H36A	109.7
C18—C17—H17A	107.5	C35—C36—H36B	109.7
C16—C17—H17A	107.5	C37—C36—H36B	109.7
C18—C17—H17B	107.5	H36A—C36—H36B	108.2
C16—C17—H17B	107.5	C41—C43—H43A	109.5
H17A—C17—H17B	107.0	C41—C43—H43B	109.5
C22—C23—C24	106 (6)	H43A—C43—H43B	109.5
C22—C23—C26	111 (6)	C41—C43—H43C	109.5
C24—C23—C26	93 (7)	H43A—C43—H43C	109.5
C22—C23—H23	114.9	H43B—C43—H43C	109.5
C24—C23—H23	114.9	C20—C29—H29A	109.5
C26—C23—H23	114.9	C20—C29—H29B	109.5
C34—C33—C32	98 (6)	H29A—C29—H29B	109.5
C34—C33—H33A	112.2	C20—C29—H29C	109.5
C32—C33—H33A	112.2	H29A—C29—H29C	109.5
C34—C33—H33B	112.2	H29B—C29—H29C	109.5
C32—C33—H33B	112.2	O14—C39—C40	113 (4)
H33A—C33—H33B	109.8	O14—C39—C38	92 (5)
C31—C45—H45A	109.5	C40—C39—C38	99 (6)
C31—C45—H45B	109.5	O14—C39—C34	122 (6)
H45A—C45—H45B	109.5	C40—C39—C34	109 (5)
C31—C45—H45C	109.5	C38—C39—C34	118 (5)
H45A—C45—H45C	109.5	C42—C41—C43	103 (7)
H45B—C45—H45C	109.5	C42—C41—C38	91 (7)
C11—C13—H13A	109.5	C43—C41—C38	117 (7)
C11—C13—H13B	109.5	C42—C41—H41	114.2
H13A—C13—H13B	109.5	C43—C41—H41	114.2
C11—C13—H13C	109.5	C38—C41—H41	114.2
H13A—C13—H13C	109.5	O13—C31—O15	107 (5)
H13B—C13—H13C	109.5	O13—C31—C45	108 (9)
C6—C7—C8	109 (5)	O15—C31—C45	102 (6)
C6—C7—H7A	109.8	O13—C31—C32	116 (7)
C8—C7—H7A	109.8	O15—C31—C32	99 (6)
C6—C7—H7B	109.8	C45—C31—C32	123 (8)

C31—O13—O14—C39	27 (6)	O4—C12—C11—C8	51 (7)
C9—O1—O2—C1	38 (7)	C9—C8—C11—C12	−45 (5)
C54—O20—O19—C46	36 (8)	C7—C8—C11—C12	82 (5)
C16—O7—O6—C24	61 (6)	C9—C8—C11—C13	−176 (5)
O6—O7—C16—O8	−78 (5)	C7—C8—C11—C13	−48 (7)
O6—O7—C16—C30	176 (4)	O7—C16—C17—C18	−84 (6)
O6—O7—C16—C17	42 (5)	O8—C16—C17—C18	37 (8)
C25—O8—C16—O7	33 (6)	C30—C16—C17—C18	152 (6)
C25—O8—C16—C30	141 (6)	O6—C24—C23—C22	169 (5)
C25—O8—C16—C17	−91 (6)	C25—C24—C23—C22	−55 (7)
O2—O1—C9—C10	19 (7)	C19—C24—C23—C22	67 (5)
O2—O1—C9—C4	−104 (5)	O6—C24—C23—C26	−79 (5)
O2—O1—C9—C8	137 (5)	C25—C24—C23—C26	58 (6)
O19—O20—C54—C55	23 (11)	C19—C24—C23—C26	180 (4)
O19—O20—C54—C49	−107 (6)	C31—C32—C33—C34	60 (9)
O19—O20—C54—C53	134 (5)	C9—C8—C7—C6	−46 (7)
C1—O3—C10—O4	−93 (5)	C11—C8—C7—C6	−180 (5)
C1—O3—C10—C9	36 (7)	C55—O17—C57—O16	140 (7)
C12—O4—C10—O3	169 (4)	C55—O17—C57—C56	−31 (11)
C12—O4—C10—C9	32 (7)	O19—C46—C47—C48	−92 (6)
O1—C9—C10—O3	−64 (8)	O18—C46—C47—C48	19 (8)
C4—C9—C10—O3	61 (7)	C60—C46—C47—C48	149 (6)
C8—C9—C10—O3	−164 (5)	C49—C48—C47—C46	56 (7)
O1—C9—C10—O4	68 (7)	O10—C27—C26—C28	−43 (11)
C4—C9—C10—O4	−168 (4)	O9—C27—C26—C28	−177 (7)
C8—C9—C10—O4	−33 (6)	O10—C27—C26—C23	−163 (9)
O7—O6—C24—C25	−6 (8)	O9—C27—C26—C23	64 (11)
O7—O6—C24—C19	−111 (6)	C22—C23—C26—C27	52 (11)
O7—O6—C24—C23	138 (5)	C24—C23—C26—C27	−56 (8)
O20—O19—C46—O18	−54 (7)	C22—C23—C26—C28	−64 (8)
O20—O19—C46—C60	158 (7)	C24—C23—C26—C28	−173 (5)
O20—O19—C46—C47	56 (6)	O16—C57—C56—C58	−12 (10)
C55—O18—C46—O19	11 (10)	O17—C57—C56—C58	159 (6)
C55—O18—C46—C60	156 (8)	O16—C57—C56—C53	−129 (8)
C55—O18—C46—C47	−93 (7)	O17—C57—C56—C53	42 (9)
C16—O8—C25—O9	−100 (4)	C54—C53—C56—C57	−70 (7)
C16—O8—C25—C24	24 (7)	C52—C53—C56—C57	72 (8)
C27—O9—C25—O8	169 (6)	C54—C53—C56—C58	178 (5)
C27—O9—C25—C24	37 (6)	C52—C53—C56—C58	−40 (8)
O6—C24—C25—O8	−38 (8)	C24—C23—C22—C21	−75 (7)
C19—C24—C25—O8	61 (6)	C26—C23—C22—C21	−174 (7)
C23—C24—C25—O8	−175 (5)	C54—C53—C52—C51	−49 (7)
O6—C24—C25—O9	87 (6)	C56—C53—C52—C51	170 (5)
C19—C24—C25—O9	−174 (4)	C40—O12—C42—O11	175 (6)
C23—C24—C25—O9	−50 (7)	C40—O12—C42—C41	−66 (11)
C46—O18—C55—O17	−81 (7)	C8—C7—C6—C5	50 (8)
C46—O18—C55—C54	36 (9)	C14—C5—C6—C7	−174 (4)
C57—O17—C55—O18	151 (6)	C4—C5—C6—C7	−51 (7)
C57—O17—C55—C54	40 (10)	C32—C33—C34—C35	−154 (6)
O20—C54—C55—O18	−55 (10)	C32—C33—C34—C39	−34 (7)
C49—C54—C55—O18	71 (6)	C24—C19—C18—C17	−19 (9)
C53—C54—C55—O18	−171 (4)	C20—C19—C18—C17	−150 (4)
O20—C54—C55—O17	62 (10)	C16—C17—C18—C19	36 (8)
C49—C54—C55—O17	−172 (5)	C39—C38—C37—C36	−28 (11)
C53—C54—C55—O17	−54 (6)	C41—C38—C37—C36	−178 (7)
C10—O4—C12—O5	169 (4)	C18—C19—C20—C29	−45 (7)
C10—O4—C12—C11	−50 (8)	C24—C19—C20—C29	174 (5)
O1—O2—C1—O3	−69 (7)	C18—C19—C20—C21	−160 (6)
O1—O2—C1—C15	171 (5)	C24—C19—C20—C21	59 (6)
O1—O2—C1—C2	49 (5)	C53—C52—C51—C50	57 (8)
C10—O3—C1—O2	25 (6)	C59—C50—C51—C52	177 (5)
C10—O3—C1—C15	152 (6)	C49—C50—C51—C52	−58 (8)
C10—O3—C1—C2	−96 (5)	C33—C34—C35—C36	176 (7)
O1—C9—C8—C7	170 (4)	C39—C34—C35—C36	46 (9)
C10—C9—C8—C7	−79 (6)	C33—C34—C35—C44	−44 (7)
C4—C9—C8—C7	54 (5)	C39—C34—C35—C44	−175 (5)
O1—C9—C8—C11	−64 (5)	O2—C1—C2—C3	−87 (5)
C10—C9—C8—C11	47 (5)	O3—C1—C2—C3	37 (7)
C4—C9—C8—C11	−180 (3)	C15—C1—C2—C3	145 (6)
C47—C48—C49—C54	−32 (6)	C4—C3—C2—C1	55 (7)
C47—C48—C49—C50	−160 (6)	C23—C22—C21—C20	67 (7)
O20—C54—C49—C48	68 (5)	C29—C20—C21—C22	175 (4)
C55—C54—C49—C48	−65 (6)	C19—C20—C21—C22	−63 (7)
C53—C54—C49—C48	−176 (4)	C44—C35—C36—C37	−179 (6)
O20—C54—C49—C50	−164 (7)	C34—C35—C36—C37	−40 (11)
C55—C54—C49—C50	62 (6)	C38—C37—C36—C35	22 (10)
C53—C54—C49—C50	−49 (6)	O13—O14—C39—C40	39 (8)
C31—O15—C40—O12	−90 (7)	O13—O14—C39—C38	140 (5)
C31—O15—C40—C39	26 (8)	O13—O14—C39—C34	−95 (6)
C42—O12—C40—O15	166 (7)	O15—C40—C39—O14	−67 (8)
C42—O12—C40—C39	55 (8)	O12—C40—C39—O14	46 (8)
O20—C54—C53—C52	157 (5)	O15—C40—C39—C38	−163 (6)
C55—C54—C53—C52	−77 (6)	O12—C40—C39—C38	−50 (6)
C49—C54—C53—C52	42 (6)	O15—C40—C39—C34	73 (7)
O20—C54—C53—C56	−53 (5)	O12—C40—C39—C34	−174 (5)
C55—C54—C53—C56	72 (5)	C37—C38—C39—O14	168 (7)
C49—C54—C53—C56	−169 (4)	C41—C38—C39—O14	−43 (7)
C48—C49—C50—C59	−59 (7)	C37—C38—C39—C40	−78 (8)
C54—C49—C50—C59	178 (5)	C41—C38—C39—C40	71 (8)
C48—C49—C50—C51	179 (4)	C37—C38—C39—C34	39 (9)
C54—C49—C50—C51	56 (6)	C41—C38—C39—C34	−172 (5)
O6—C24—C19—C18	58 (7)	C33—C34—C39—O14	81 (7)
C25—C24—C19—C18	−53 (7)	C35—C34—C39—O14	−151 (7)
C23—C24—C19—C18	171 (6)	C33—C34—C39—C40	−55 (9)
O6—C24—C19—C20	−169 (5)	C35—C34—C39—C40	73 (6)
C25—C24—C19—C20	80 (5)	C33—C34—C39—C38	−166 (6)
C23—C24—C19—C20	−56 (5)	C35—C34—C39—C38	−38 (6)
C2—C3—C4—C9	−35 (6)	O11—C42—C41—C43	−61 (11)
C2—C3—C4—C5	−160 (5)	O12—C42—C41—C43	−177 (8)
O1—C9—C4—C3	73 (6)	O11—C42—C41—C38	−180 (10)
C10—C9—C4—C3	−49 (5)	O12—C42—C41—C38	65 (10)
C8—C9—C4—C3	176 (4)	C37—C38—C41—C42	78 (9)
O1—C9—C4—C5	−160 (6)	C39—C38—C41—C42	−74 (8)
C10—C9—C4—C5	78 (6)	C37—C38—C41—C43	−27 (10)
C8—C9—C4—C5	−57 (6)	C39—C38—C41—C43	−180 (5)
C25—O9—C27—O10	171 (5)	O14—O13—C31—O15	−66 (7)
C25—O9—C27—C26	−48 (9)	O14—O13—C31—C45	−175 (6)
C3—C4—C5—C14	−62 (7)	O14—O13—C31—C32	43 (6)
C9—C4—C5—C14	176 (6)	C40—O15—C31—O13	35 (8)
C3—C4—C5—C6	171 (5)	C40—O15—C31—C45	148 (9)
C9—C4—C5—C6	50 (6)	C40—O15—C31—C32	−86 (7)
O5—C12—C11—C13	−46 (8)	C33—C32—C31—O13	−98 (9)
O4—C12—C11—C13	173 (7)	C33—C32—C31—O15	16 (11)
O5—C12—C11—C8	−168 (5)	C33—C32—C31—C45	127 (10)

Artemisinin (FormIII_1) top

Crystal data top

C₁₅H₂₁O₅	F(000) = 608
M_r = 282.32	D_x = 1.537 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 9.344 (2) Å	Cell parameters from 831 reflections
b = 14.133 (3) Å	θ = 2.7–22.6°
c = 9.554 (5) Å	µ = 0.11 mm⁻¹
β = 104.73 (4)°	T = 295 K
V = 1220.2 (8) Å³	Prism, clear colourless
Z = 4	0.2 × 0.1 × 0.09 mm

Data collection top

Bruker Photon III diffractometer	1335 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	630 reflections with I > 2σ(I)
Mirror optics monochromator	R_int = 0.150
Detector resolution: 7.9 pixels mm^-1	θ_max = 23.5°, θ_min = 2.3°
ω scans	h = −10→10
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1413 before and 0.0830 after correction. The Ratio of minimum to maximum transmission is 0.6593. The λ/2 correction factor is Not present.	k = −15→15
T_min = 0.491, T_max = 0.745	l = −4→4
6348 measured 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)] = 0.074	w = 1/[σ²(F_o²) + (0.1689P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.252	(Δ/σ)_max < 0.001
S = 0.86	Δρ_max = 0.19 e Å⁻³
1335 reflections	Δρ_min = −0.23 e Å⁻³
167 parameters	Absolute structure: Flack x determined using 213 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
47 restraints	Absolute structure parameter: 0.5 (10)

Special details top

Refinement. Distance (DFIX) restraints were applied based on mogul geometry check from mercury.

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

	x	y	z	U_iso*/U_eq
O3A	0.7976 (14)	0.3098 (9)	0.720 (3)	0.029 (5)*
O1A	1.0206 (17)	0.2308 (9)	0.806 (3)	0.036 (5)*
O2A	1.1077 (14)	0.3149 (8)	0.863 (4)	0.032 (5)*
O4A	0.8335 (15)	0.3106 (10)	0.969 (4)	0.026 (5)*
O5A	0.8522 (17)	0.3075 (11)	1.207 (4)	0.039 (5)*
C15A	0.836 (3)	0.1631 (15)	0.619 (6)	0.036 (7)*
H15A	0.805189	0.129156	0.693605	0.054*
H15B	0.904641	0.125365	0.584001	0.054*
H15C	0.750987	0.176759	0.541070	0.054*
C4A	0.909 (2)	0.2542 (12)	0.680 (3)	0.034 (8)*
C5A	0.852 (2)	0.3649 (15)	0.845 (4)	0.030 (7)*
H5A	0.790727	0.421883	0.837042	0.036*
C6A	1.0128 (19)	0.3962 (11)	0.863 (4)	0.031 (8)*
C1A	1.021 (3)	0.4628 (13)	0.739 (5)	0.028 (6)*
H1A	1.125826	0.477073	0.750041	0.034*
C2A	0.962 (3)	0.4212 (13)	0.588 (5)	0.050 (9)*
H2AA	1.018269	0.448829	0.525070	0.060*
H2AB	0.860333	0.441325	0.551285	0.060*
C3A	0.967 (3)	0.3134 (13)	0.573 (4)	0.037 (7)*
H3AA	0.911333	0.296697	0.475799	0.044*
H3AB	1.069338	0.295205	0.581322	0.044*
C12A	0.905 (2)	0.3291 (16)	1.108 (4)	0.035 (9)*
C11A	1.060 (2)	0.3687 (17)	1.131 (4)	0.040 (8)*
H11A	1.122068	0.314819	1.120262	0.048*
C13A	1.119 (3)	0.4039 (18)	1.286 (5)	0.039 (8)*
H13A	1.055649	0.452653	1.305655	0.059*
H13B	1.217156	0.428929	1.297264	0.059*
H13C	1.122709	0.352326	1.351902	0.059*
C7A	1.073 (3)	0.4395 (11)	1.013 (4)	0.023 (7)*
H7A	1.178511	0.451653	1.024595	0.027*
C8A	1.000 (3)	0.5342 (12)	1.032 (5)	0.034 (8)*
H8AA	0.897917	0.523984	1.033503	0.040*
H8AB	1.051519	0.562890	1.123225	0.040*
C9A	1.007 (3)	0.6001 (16)	0.907 (4)	0.034 (7)*
H9AA	0.952780	0.657486	0.915133	0.040*
H9AB	1.109288	0.617507	0.916075	0.040*
C10A	0.944 (2)	0.5576 (12)	0.757 (4)	0.022 (6)*
H10A	0.838373	0.545109	0.745310	0.027*
C14A	0.960 (3)	0.6277 (17)	0.641 (5)	0.035 (8)*
H14A	1.062501	0.639909	0.649742	0.053*
H14B	0.910565	0.685721	0.652946	0.053*
H14C	0.915368	0.601699	0.547113	0.053*
O3B	0.3126 (17)	0.0083 (11)	0.719 (4)	0.039 (5)*
O1B	0.5585 (18)	−0.0359 (9)	0.807 (4)	0.038 (5)*
O2B	0.6159 (15)	0.0600 (8)	0.847 (4)	0.028 (4)*
O4B	0.3497 (18)	0.0163 (12)	0.965 (4)	0.038 (6)*
O5B	0.3887 (19)	0.0150 (12)	1.206 (4)	0.042 (5)*
C15B	0.406 (3)	−0.1267 (14)	0.638 (7)	0.042 (8)*
H15D	0.365698	−0.156430	0.710009	0.062*
H15E	0.494610	−0.159190	0.632332	0.062*
H15F	0.335008	−0.129311	0.545942	0.062*
C4B	0.442 (2)	−0.0250 (13)	0.679 (3)	0.036 (7)*
C5B	0.350 (2)	0.0697 (16)	0.837 (4)	0.034 (8)*
H5B	0.270867	0.116561	0.824157	0.041*
C11B	0.568 (3)	0.0956 (17)	1.117 (4)	0.048 (9)*
H11B	0.643244	0.050995	1.101147	0.058*
C6B	0.4946 (19)	0.1246 (12)	0.853 (4)	0.027 (7)*
C1B	0.482 (2)	0.1924 (11)	0.726 (4)	0.018 (6)*
H1B	0.581359	0.216314	0.729884	0.022*
C2B	0.422 (3)	0.1438 (12)	0.581 (4)	0.038 (8)*
H2BA	0.449945	0.182154	0.507756	0.046*
H2BB	0.315212	0.144558	0.559918	0.046*
C3B	0.471 (3)	0.0412 (11)	0.563 (4)	0.037 (8)*
H3BA	0.417561	0.017962	0.468212	0.045*
H3BB	0.575596	0.040468	0.566552	0.045*
C12B	0.426 (3)	0.0401 (15)	1.099 (4)	0.032 (9)*
C13B	0.623 (3)	0.1323 (16)	1.271 (5)	0.027 (7)*
H13D	0.545970	0.168931	1.295515	0.040*
H13E	0.708534	0.171187	1.278741	0.040*
H13F	0.647725	0.079720	1.336482	0.040*
C7B	0.553 (2)	0.1733 (13)	1.000 (4)	0.030 (7)*
H7B	0.651461	0.198888	1.004371	0.036*
C8B	0.452 (3)	0.2556 (13)	1.023 (5)	0.031 (7)*
H8BA	0.354858	0.232157	1.023772	0.037*
H8BB	0.494590	0.287553	1.113581	0.037*
C9B	0.441 (3)	0.3231 (16)	0.896 (4)	0.046 (8)*
H9BA	0.538393	0.349889	0.902648	0.055*
H9BB	0.375494	0.374638	0.904267	0.055*
C10B	0.385 (3)	0.2771 (13)	0.747 (4)	0.032 (7)*
H10B	0.284657	0.253886	0.738884	0.039*
C14B	0.379 (3)	0.3497 (16)	0.626 (5)	0.036 (7)*
H14D	0.477533	0.368125	0.625585	0.054*
H14E	0.324430	0.404304	0.643102	0.054*
H14F	0.330563	0.322038	0.534712	0.054*

Geometric parameters (Å, º) top

O3A—C4A	1.431 (14)	O3B—C4B	1.435 (14)
O3A—C5A	1.407 (15)	O3B—C5B	1.395 (15)
O1A—O2A	1.464 (13)	O1B—O2B	1.473 (13)
O1A—C4A	1.416 (15)	O1B—C4B	1.419 (15)
O2A—C6A	1.452 (14)	O2B—C6B	1.469 (14)
O4A—C5A	1.455 (15)	O4B—C5B	1.438 (15)
O4A—C12A	1.353 (15)	O4B—C12B	1.346 (15)
O5A—C12A	1.215 (15)	O5B—C12B	1.216 (15)
C15A—H15A	0.9600	C15B—H15D	0.9600
C15A—H15B	0.9600	C15B—H15E	0.9600
C15A—H15C	0.9600	C15B—H15F	0.9600
C15A—C4A	1.503 (15)	C15B—C4B	1.506 (14)
C4A—C3A	1.529 (15)	C4B—C3B	1.531 (15)
C5A—H5A	0.9800	C5B—H5B	0.9800
C5A—C6A	1.532 (14)	C5B—C6B	1.527 (14)
C6A—C1A	1.528 (15)	C11B—H11B	0.9800
C6A—C7A	1.528 (15)	C11B—C12B	1.516 (15)
C1A—H1A	0.9800	C11B—C13B	1.525 (15)
C1A—C2A	1.528 (15)	C11B—C7B	1.544 (15)
C1A—C10A	1.551 (14)	C6B—C1B	1.525 (15)
C2A—H2AA	0.9700	C6B—C7B	1.533 (15)
C2A—H2AB	0.9700	C1B—H1B	0.9800
C2A—C3A	1.532 (14)	C1B—C2B	1.524 (15)
C3A—H3AA	0.9700	C1B—C10B	1.543 (14)
C3A—H3AB	0.9700	C2B—H2BA	0.9700
C12A—C11A	1.513 (15)	C2B—H2BB	0.9700
C11A—H11A	0.9800	C2B—C3B	1.543 (14)
C11A—C13A	1.529 (15)	C3B—H3BA	0.9700
C11A—C7A	1.535 (15)	C3B—H3BB	0.9700
C13A—H13A	0.9600	C13B—H13D	0.9600
C13A—H13B	0.9600	C13B—H13E	0.9600
C13A—H13C	0.9600	C13B—H13F	0.9600
C7A—H7A	0.9800	C7B—H7B	0.9800
C7A—C8A	1.533 (14)	C7B—C8B	1.546 (14)
C8A—H8AA	0.9700	C8B—H8BA	0.9700
C8A—H8AB	0.9700	C8B—H8BB	0.9700
C8A—C9A	1.528 (15)	C8B—C9B	1.523 (15)
C9A—H9AA	0.9700	C9B—H9BA	0.9700
C9A—H9AB	0.9700	C9B—H9BB	0.9700
C9A—C10A	1.527 (15)	C9B—C10B	1.530 (15)
C10A—H10A	0.9800	C10B—H10B	0.9800
C10A—C14A	1.521 (15)	C10B—C14B	1.533 (15)
C14A—H14A	0.9600	C14B—H14D	0.9600
C14A—H14B	0.9600	C14B—H14E	0.9600
C14A—H14C	0.9600	C14B—H14F	0.9600

C5A—O3A—C4A	113.6 (17)	C5B—O3B—C4B	111.0 (19)
C4A—O1A—O2A	110.3 (16)	C4B—O1B—O2B	105.8 (17)
C6A—O2A—O1A	111.2 (13)	C6B—O2B—O1B	110.4 (12)
C12A—O4A—C5A	124.3 (16)	C12B—O4B—C5B	124.3 (18)
H15A—C15A—H15B	109.5	H15D—C15B—H15E	109.5
H15A—C15A—H15C	109.5	H15D—C15B—H15F	109.5
H15B—C15A—H15C	109.5	H15E—C15B—H15F	109.5
C4A—C15A—H15A	109.5	C4B—C15B—H15D	109.5
C4A—C15A—H15B	109.5	C4B—C15B—H15E	109.5
C4A—C15A—H15C	109.5	C4B—C15B—H15F	109.5
O3A—C4A—C15A	106.5 (17)	O3B—C4B—C15B	103.5 (17)
O3A—C4A—C3A	106.7 (18)	O3B—C4B—C3B	108 (2)
O1A—C4A—O3A	109.3 (18)	O1B—C4B—O3B	109.0 (18)
O1A—C4A—C15A	107 (2)	O1B—C4B—C15B	101 (3)
O1A—C4A—C3A	112.6 (19)	O1B—C4B—C3B	116.9 (19)
C15A—C4A—C3A	114 (2)	C15B—C4B—C3B	117 (2)
O3A—C5A—O4A	107.6 (18)	O3B—C5B—O4B	108 (2)
O3A—C5A—H5A	108.0	O3B—C5B—H5B	107.0
O3A—C5A—C6A	113 (2)	O3B—C5B—C6B	116 (2)
O4A—C5A—H5A	108.0	O4B—C5B—H5B	107.0
O4A—C5A—C6A	112 (2)	O4B—C5B—C6B	112 (2)
C6A—C5A—H5A	108.0	C6B—C5B—H5B	107.0
O2A—C6A—C5A	110.7 (15)	C12B—C11B—H11B	106.8
O2A—C6A—C1A	110 (2)	C12B—C11B—C13B	110 (2)
O2A—C6A—C7A	104 (2)	C12B—C11B—C7B	112 (2)
C1A—C6A—C5A	109.4 (19)	C13B—C11B—H11B	106.8
C7A—C6A—C5A	110 (2)	C13B—C11B—C7B	114 (2)
C7A—C6A—C1A	113.6 (18)	C7B—C11B—H11B	106.8
C6A—C1A—H1A	106.8	O2B—C6B—C5B	110.5 (15)
C6A—C1A—C10A	109 (2)	O2B—C6B—C1B	105.2 (19)
C2A—C1A—C6A	115 (2)	O2B—C6B—C7B	103 (2)
C2A—C1A—H1A	106.8	C5B—C6B—C7B	115 (2)
C2A—C1A—C10A	112 (2)	C1B—C6B—C5B	110 (2)
C10A—C1A—H1A	106.8	C1B—C6B—C7B	112.4 (16)
C1A—C2A—H2AA	108.0	C6B—C1B—H1B	108.0
C1A—C2A—H2AB	108.0	C6B—C1B—C10B	108 (2)
C1A—C2A—C3A	117 (3)	C2B—C1B—C6B	112.2 (17)
H2AA—C2A—H2AB	107.2	C2B—C1B—H1B	108.0
C3A—C2A—H2AA	108.0	C2B—C1B—C10B	112 (2)
C3A—C2A—H2AB	108.0	C10B—C1B—H1B	108.0
C4A—C3A—C2A	117 (2)	C1B—C2B—H2BA	107.7
C4A—C3A—H3AA	108.0	C1B—C2B—H2BB	107.7
C4A—C3A—H3AB	108.0	C1B—C2B—C3B	119 (3)
C2A—C3A—H3AA	108.0	H2BA—C2B—H2BB	107.1
C2A—C3A—H3AB	108.0	C3B—C2B—H2BA	107.7
H3AA—C3A—H3AB	107.2	C3B—C2B—H2BB	107.7
O4A—C12A—C11A	115 (2)	C4B—C3B—C2B	112 (2)
O5A—C12A—O4A	122 (2)	C4B—C3B—H3BA	109.1
O5A—C12A—C11A	123 (3)	C4B—C3B—H3BB	109.1
C12A—C11A—H11A	105.7	C2B—C3B—H3BA	109.1
C12A—C11A—C13A	111 (2)	C2B—C3B—H3BB	109.1
C12A—C11A—C7A	113 (2)	H3BA—C3B—H3BB	107.9
C13A—C11A—H11A	105.7	O4B—C12B—C11B	118 (3)
C13A—C11A—C7A	115 (2)	O5B—C12B—O4B	122 (2)
C7A—C11A—H11A	105.7	O5B—C12B—C11B	119 (3)
C11A—C13A—H13A	109.5	C11B—C13B—H13D	109.5
C11A—C13A—H13B	109.5	C11B—C13B—H13E	109.5
C11A—C13A—H13C	109.5	C11B—C13B—H13F	109.5
H13A—C13A—H13B	109.5	H13D—C13B—H13E	109.5
H13A—C13A—H13C	109.5	H13D—C13B—H13F	109.5
H13B—C13A—H13C	109.5	H13E—C13B—H13F	109.5
C6A—C7A—C11A	110.3 (18)	C11B—C7B—H7B	108.4
C6A—C7A—H7A	107.3	C11B—C7B—C8B	113 (2)
C6A—C7A—C8A	113 (2)	C6B—C7B—C11B	107 (2)
C11A—C7A—H7A	107.3	C6B—C7B—H7B	108.4
C8A—C7A—C11A	111 (2)	C6B—C7B—C8B	112 (2)
C8A—C7A—H7A	107.3	C8B—C7B—H7B	108.4
C7A—C8A—H8AA	109.8	C7B—C8B—H8BA	110.5
C7A—C8A—H8AB	109.8	C7B—C8B—H8BB	110.5
H8AA—C8A—H8AB	108.3	H8BA—C8B—H8BB	108.7
C9A—C8A—C7A	109 (2)	C9B—C8B—C7B	106 (2)
C9A—C8A—H8AA	109.8	C9B—C8B—H8BA	110.5
C9A—C8A—H8AB	109.8	C9B—C8B—H8BB	110.5
C8A—C9A—H9AA	108.7	C8B—C9B—H9BA	108.7
C8A—C9A—H9AB	108.7	C8B—C9B—H9BB	108.7
H9AA—C9A—H9AB	107.6	C8B—C9B—C10B	114 (2)
C10A—C9A—C8A	114 (2)	H9BA—C9B—H9BB	107.6
C10A—C9A—H9AA	108.7	C10B—C9B—H9BA	108.7
C10A—C9A—H9AB	108.7	C10B—C9B—H9BB	108.7
C1A—C10A—H10A	108.3	C1B—C10B—H10B	108.1
C9A—C10A—C1A	111 (2)	C9B—C10B—C1B	112 (2)
C9A—C10A—H10A	108.3	C9B—C10B—H10B	108.1
C14A—C10A—C1A	110 (2)	C9B—C10B—C14B	111 (2)
C14A—C10A—C9A	110.0 (19)	C14B—C10B—C1B	110 (2)
C14A—C10A—H10A	108.3	C14B—C10B—H10B	108.1
C10A—C14A—H14A	109.5	C10B—C14B—H14D	109.5
C10A—C14A—H14B	109.5	C10B—C14B—H14E	109.5
C10A—C14A—H14C	109.5	C10B—C14B—H14F	109.5
H14A—C14A—H14B	109.5	H14D—C14B—H14E	109.5
H14A—C14A—H14C	109.5	H14D—C14B—H14F	109.5
H14B—C14A—H14C	109.5	H14E—C14B—H14F	109.5

O3A—C4A—C3A—C2A	29 (3)	O3B—C4B—C3B—C2B	32 (3)
O3A—C5A—C6A—O2A	−56 (3)	O3B—C5B—C6B—O2B	−51 (4)
O3A—C5A—C6A—C1A	65 (2)	O3B—C5B—C6B—C1B	65 (2)
O3A—C5A—C6A—C7A	−169.7 (16)	O3B—C5B—C6B—C7B	−166.4 (18)
O1A—O2A—C6A—C5A	16 (4)	O1B—O2B—C6B—C5B	8 (4)
O1A—O2A—C6A—C1A	−105 (2)	O1B—O2B—C6B—C1B	−111 (2)
O1A—O2A—C6A—C7A	134 (2)	O1B—O2B—C6B—C7B	131 (2)
O1A—C4A—C3A—C2A	−91 (3)	O1B—C4B—C3B—C2B	−91 (3)
O2A—O1A—C4A—O3A	−71 (2)	O2B—O1B—C4B—O3B	−78.4 (19)
O2A—O1A—C4A—C15A	174 (2)	O2B—O1B—C4B—C15B	173 (2)
O2A—O1A—C4A—C3A	47 (2)	O2B—O1B—C4B—C3B	44 (2)
O2A—C6A—C1A—C2A	64 (2)	O2B—C6B—C1B—C2B	70 (2)
O2A—C6A—C1A—C10A	−169 (2)	O2B—C6B—C1B—C10B	−166 (2)
O2A—C6A—C7A—C11A	−61 (2)	O2B—C6B—C7B—C11B	−64 (2)
O2A—C6A—C7A—C8A	173.3 (19)	O2B—C6B—C7B—C8B	172.1 (19)
O4A—C5A—C6A—O2A	66 (3)	O4B—C5B—C6B—O2B	73 (3)
O4A—C5A—C6A—C1A	−173.1 (16)	O4B—C5B—C6B—C1B	−170.8 (17)
O4A—C5A—C6A—C7A	−48 (2)	O4B—C5B—C6B—C7B	−42 (2)
O4A—C12A—C11A—C13A	170 (2)	C15B—C4B—C3B—C2B	148 (2)
O4A—C12A—C11A—C7A	39 (3)	C4B—O3B—C5B—O4B	−98 (2)
O5A—C12A—C11A—C13A	−17 (3)	C4B—O3B—C5B—C6B	28 (3)
O5A—C12A—C11A—C7A	−147 (2)	C4B—O1B—O2B—C6B	52 (3)
C15A—C4A—C3A—C2A	147 (3)	C5B—O3B—C4B—O1B	35 (2)
C4A—O3A—C5A—O4A	−93 (2)	C5B—O3B—C4B—C15B	142 (3)
C4A—O3A—C5A—C6A	31 (2)	C5B—O3B—C4B—C3B	−93 (2)
C4A—O1A—O2A—C6A	44 (3)	C5B—O4B—C12B—O5B	155 (2)
C5A—O3A—C4A—O1A	30 (2)	C5B—O4B—C12B—C11B	−29 (3)
C5A—O3A—C4A—C15A	145 (2)	C5B—C6B—C1B—C2B	−50 (2)
C5A—O3A—C4A—C3A	−92 (2)	C5B—C6B—C1B—C10B	75 (2)
C5A—O4A—C12A—O5A	153 (2)	C5B—C6B—C7B—C11B	56 (2)
C5A—O4A—C12A—C11A	−33 (3)	C5B—C6B—C7B—C8B	−68 (2)
C5A—C6A—C1A—C2A	−58 (2)	C11B—C7B—C8B—C9B	−177 (2)
C5A—C6A—C1A—C10A	69 (2)	C6B—C1B—C2B—C3B	−37 (3)
C5A—C6A—C7A—C11A	57 (2)	C6B—C1B—C10B—C9B	53 (2)
C5A—C6A—C7A—C8A	−68 (2)	C6B—C1B—C10B—C14B	176.4 (19)
C6A—C1A—C2A—C3A	−26 (3)	C6B—C7B—C8B—C9B	−57 (2)
C6A—C1A—C10A—C9A	54 (2)	C1B—C6B—C7B—C11B	−176.7 (15)
C6A—C1A—C10A—C14A	176 (2)	C1B—C6B—C7B—C8B	60 (2)
C6A—C7A—C8A—C9A	−51 (2)	C1B—C2B—C3B—C4B	54 (3)
C1A—C6A—C7A—C11A	179.5 (14)	C2B—C1B—C10B—C9B	177 (2)
C1A—C6A—C7A—C8A	54 (2)	C2B—C1B—C10B—C14B	−59 (3)
C1A—C2A—C3A—C4A	48 (3)	C12B—O4B—C5B—O3B	156.3 (19)
C2A—C1A—C10A—C9A	−178 (2)	C12B—O4B—C5B—C6B	28 (3)
C2A—C1A—C10A—C14A	−56 (3)	C12B—C11B—C7B—C6B	−53 (3)
C12A—O4A—C5A—O3A	162.7 (17)	C12B—C11B—C7B—C8B	71 (3)
C12A—O4A—C5A—C6A	38 (3)	C13B—C11B—C12B—O4B	169 (2)
C12A—C11A—C7A—C6A	−52 (3)	C13B—C11B—C12B—O5B	−14 (3)
C12A—C11A—C7A—C8A	74 (3)	C13B—C11B—C7B—C6B	−178.8 (18)
C11A—C7A—C8A—C9A	−176 (2)	C13B—C11B—C7B—C8B	−55 (3)
C13A—C11A—C7A—C6A	178.8 (17)	C7B—C11B—C12B—O4B	41 (3)
C13A—C11A—C7A—C8A	−55 (3)	C7B—C11B—C12B—O5B	−142 (2)
C7A—C6A—C1A—C2A	179.7 (17)	C7B—C6B—C1B—C2B	−179.3 (16)
C7A—C6A—C1A—C10A	−54 (2)	C7B—C6B—C1B—C10B	−55 (2)
C7A—C8A—C9A—C10A	53 (3)	C7B—C8B—C9B—C10B	56 (3)
C8A—C9A—C10A—C1A	−56 (3)	C8B—C9B—C10B—C1B	−57 (3)
C8A—C9A—C10A—C14A	−178.6 (16)	C8B—C9B—C10B—C14B	−179.6 (18)
C10A—C1A—C2A—C3A	−152 (2)	C10B—C1B—C2B—C3B	−160 (2)

Artemisinin (FormIII_2) top

Crystal data top

C₁₅H₂₂O₅	F(000) = 608
M_r = 282.32	D_x = 1.598 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 9.186 (3) Å	Cell parameters from 578 reflections
b = 13.927 (5) Å	θ = 2.7–21.1°
c = 9.469 (8) Å	µ = 0.12 mm⁻¹
β = 104.43 (6)°	T = 296 K
V = 1173.1 (12) Å³	Prism, clear colourless
Z = 4	0.2 × 0.1 × 0.09 mm

Data collection top

Bruker D8 Venture diffractometer	1256 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	440 reflections with I > 2σ(I)
Mirror optics monochromator	R_int = 0.276
ω scans	θ_max = 23.4°, θ_min = 2.3°
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1836 before and 0.0967 after correction. The Ratio of minimum to maximum transmission is 0.5160. The λ/2 correction factor is Not present.	h = −10→10
T_min = 0.384, T_max = 0.745	k = −15→15
5153 measured reflections	l = −4→4

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.154	w = 1/[σ²(F_o²) + (0.2P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.441	(Δ/σ)_max < 0.001
S = 1.06	Δρ_max = 0.52 e Å⁻³
1256 reflections	Δρ_min = −0.48 e Å⁻³
167 parameters	Absolute structure: Flack x determined using 93 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
47 restraints	Absolute structure parameter: −4.9 (10)

Special details top

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

	x	y	z	U_iso*/U_eq
O3A	0.791 (3)	0.308 (2)	0.716 (7)	0.048 (11)*
O1A	1.022 (3)	0.2276 (17)	0.798 (6)	0.035 (9)*
O2A	1.103 (3)	0.3170 (15)	0.848 (7)	0.034 (9)*
O4A	0.833 (3)	0.312 (2)	0.972 (7)	0.040 (10)*
O5A	0.849 (4)	0.313 (3)	1.210 (8)	0.064 (12)*
C15A	0.845 (6)	0.159 (3)	0.645 (13)	0.055 (18)*
H15A	0.761025	0.153740	0.688724	0.082*
H15B	0.919288	0.112152	0.687479	0.082*
H15C	0.811016	0.148657	0.542229	0.082*
C4A	0.912 (4)	0.259 (2)	0.674 (6)	0.046 (17)*
C5A	0.845 (3)	0.363 (3)	0.842 (7)	0.034 (15)*
H5A	0.782102	0.420666	0.833485	0.040*
C6A	1.009 (3)	0.397 (2)	0.872 (7)	0.018 (12)*
C1A	1.019 (5)	0.466 (2)	0.748 (8)	0.028 (13)*
H1A	1.126350	0.478173	0.759087	0.034*
C2A	0.961 (5)	0.421 (3)	0.598 (9)	0.051 (18)*
H2AA	1.008791	0.455440	0.533269	0.062*
H2AB	0.854747	0.436865	0.567644	0.062*
C3A	0.971 (5)	0.314 (3)	0.559 (7)	0.051 (16)*
H3AA	0.909087	0.300866	0.462138	0.061*
H3AB	1.073629	0.296164	0.563554	0.061*
C12A	0.907 (4)	0.329 (3)	1.111 (8)	0.034 (17)*
C11A	1.067 (5)	0.368 (4)	1.147 (7)	0.056 (18)*
H11A	1.132458	0.314051	1.139352	0.068*
C13A	1.126 (5)	0.410 (3)	1.300 (8)	0.041 (15)*
H13A	1.049605	0.449413	1.324029	0.061*
H13B	1.213549	0.447934	1.302985	0.061*
H13C	1.151142	0.358533	1.369651	0.061*
C7A	1.075 (4)	0.439 (2)	1.025 (6)	0.014 (11)*
H7A	1.181552	0.451479	1.032652	0.016*
C8A	1.004 (6)	0.535 (2)	1.054 (9)	0.049 (17)*
H8AA	0.898814	0.525333	1.052998	0.059*
H8AB	1.055771	0.559663	1.149078	0.059*
C9A	1.019 (5)	0.604 (3)	0.934 (9)	0.031 (14)*
H9AA	1.124131	0.618361	0.944251	0.037*
H9AB	0.968042	0.663672	0.944929	0.037*
C10A	0.952 (6)	0.564 (3)	0.782 (9)	0.044 (15)*
H10A	0.844883	0.552259	0.774029	0.053*
C14A	0.961 (5)	0.630 (4)	0.657 (9)	0.048 (18)*
H14A	1.062120	0.652806	0.669887	0.072*
H14B	0.895192	0.684365	0.655229	0.072*
H14C	0.930390	0.596448	0.565777	0.072*
O3B	0.308 (3)	0.005 (2)	0.720 (7)	0.041 (10)*
O1B	0.556 (4)	−0.0391 (19)	0.797 (7)	0.046 (10)*
O2B	0.611 (3)	0.0593 (18)	0.840 (8)	0.048 (11)*
O4B	0.350 (4)	0.014 (3)	0.977 (7)	0.052 (12)*
O5B	0.389 (4)	0.012 (3)	1.213 (8)	0.054 (11)*
C15B	0.405 (7)	−0.131 (3)	0.645 (16)	0.057 (18)*
H15D	0.379987	−0.159021	0.728808	0.086*
H15E	0.491993	−0.162648	0.628181	0.086*
H15F	0.321797	−0.139361	0.561170	0.086*
C4B	0.437 (4)	−0.026 (3)	0.671 (6)	0.057 (19)*
C5B	0.351 (4)	0.063 (3)	0.844 (7)	0.033 (15)*
H5B	0.269719	0.110318	0.832363	0.039*
C11B	0.573 (4)	0.100 (3)	1.129 (7)	0.028 (14)*
H11B	0.645769	0.053078	1.111084	0.033*
C6B	0.492 (3)	0.124 (2)	0.857 (7)	0.018 (12)*
C1B	0.478 (4)	0.192 (2)	0.727 (7)	0.022 (12)*
H1B	0.578983	0.216541	0.731942	0.027*
C2B	0.425 (5)	0.142 (3)	0.579 (8)	0.040 (15)*
H2BA	0.454062	0.182580	0.507764	0.048*
H2BB	0.316248	0.141074	0.555358	0.048*
C3B	0.477 (6)	0.039 (2)	0.555 (8)	0.051 (18)*
H3BA	0.426155	0.017022	0.458505	0.062*
H3BB	0.584232	0.038246	0.564570	0.062*
C12B	0.429 (4)	0.042 (3)	1.109 (8)	0.027 (16)*
C13B	0.636 (4)	0.129 (3)	1.288 (8)	0.020 (12)*
H13D	0.563222	0.166612	1.320559	0.030*
H13E	0.726013	0.165884	1.296527	0.030*
H13F	0.659307	0.072288	1.347728	0.030*
C7B	0.556 (5)	0.173 (2)	1.004 (6)	0.030 (13)*
H7B	0.656097	0.197697	1.005461	0.036*
C8B	0.457 (5)	0.257 (3)	1.030 (8)	0.035 (14)*
H8BA	0.360180	0.234144	1.038175	0.042*
H8BB	0.505452	0.291468	1.118000	0.042*
C9B	0.440 (5)	0.322 (3)	0.897 (8)	0.042 (15)*
H9BA	0.536985	0.350094	0.900288	0.051*
H9BB	0.372818	0.373970	0.906593	0.051*
C10B	0.380 (5)	0.279 (3)	0.745 (8)	0.037 (14)*
H10B	0.277330	0.256243	0.735475	0.045*
C14B	0.379 (6)	0.351 (4)	0.624 (9)	0.060 (18)*
H14D	0.476766	0.380412	0.639471	0.090*
H14E	0.305779	0.400210	0.625642	0.090*
H14F	0.354368	0.319583	0.531256	0.090*

Geometric parameters (Å, º) top

O3A—C4A	1.440 (15)	O3B—C4B	1.440 (15)
O3A—C5A	1.408 (15)	O3B—C5B	1.400 (15)
O1A—O2A	1.467 (15)	O1B—O2B	1.480 (15)
O1A—C4A	1.415 (16)	O1B—C4B	1.418 (16)
O2A—C6A	1.460 (15)	O2B—C6B	1.458 (15)
O4A—C5A	1.452 (15)	O4B—C5B	1.439 (15)
O4A—C12A	1.350 (16)	O4B—C12B	1.337 (16)
O5A—C12A	1.209 (15)	O5B—C12B	1.205 (16)
C15A—H15A	0.9600	C15B—H15D	0.9600
C15A—H15B	0.9600	C15B—H15E	0.9600
C15A—H15C	0.9600	C15B—H15F	0.9600
C15A—C4A	1.516 (15)	C15B—C4B	1.510 (15)
C4A—C3A	1.529 (16)	C4B—C3B	1.534 (16)
C5A—H5A	0.9800	C5B—H5B	0.9800
C5A—C6A	1.533 (15)	C5B—C6B	1.525 (15)
C6A—C1A	1.537 (15)	C11B—H11B	0.9800
C6A—C7A	1.537 (16)	C11B—C12B	1.515 (15)
C1A—H1A	0.9800	C11B—C13B	1.527 (16)
C1A—C2A	1.532 (16)	C11B—C7B	1.541 (16)
C1A—C10A	1.550 (15)	C6B—C1B	1.531 (15)
C2A—H2AA	0.9700	C6B—C7B	1.535 (16)
C2A—H2AB	0.9700	C1B—H1B	0.9800
C2A—C3A	1.537 (15)	C1B—C2B	1.526 (16)
C3A—H3AA	0.9700	C1B—C10B	1.538 (15)
C3A—H3AB	0.9700	C2B—H2BA	0.9700
C12A—C11A	1.521 (15)	C2B—H2BB	0.9700
C11A—H11A	0.9800	C2B—C3B	1.538 (15)
C11A—C13A	1.528 (16)	C3B—H3BA	0.9700
C11A—C7A	1.540 (16)	C3B—H3BB	0.9700
C13A—H13A	0.9600	C13B—H13D	0.9600
C13A—H13B	0.9600	C13B—H13E	0.9600
C13A—H13C	0.9600	C13B—H13F	0.9600
C7A—H7A	0.9800	C7B—H7B	0.9800
C7A—C8A	1.541 (15)	C7B—C8B	1.539 (15)
C8A—H8AA	0.9700	C8B—H8BA	0.9700
C8A—H8AB	0.9700	C8B—H8BB	0.9700
C8A—C9A	1.527 (16)	C8B—C9B	1.525 (16)
C9A—H9AA	0.9700	C9B—H9BA	0.9700
C9A—H9AB	0.9700	C9B—H9BB	0.9700
C9A—C10A	1.528 (16)	C9B—C10B	1.529 (16)
C10A—H10A	0.9800	C10B—H10B	0.9800
C10A—C14A	1.525 (16)	C10B—C14B	1.526 (16)
C14A—H14A	0.9600	C14B—H14D	0.9600
C14A—H14B	0.9600	C14B—H14E	0.9600
C14A—H14C	0.9600	C14B—H14F	0.9600

C5A—O3A—C4A	111 (3)	C5B—O3B—C4B	111 (4)
C4A—O1A—O2A	102 (3)	C4B—O1B—O2B	104 (4)
C6A—O2A—O1A	115 (2)	C6B—O2B—O1B	113 (2)
C12A—O4A—C5A	128 (3)	C12B—O4B—C5B	124 (4)
H15A—C15A—H15B	109.5	H15D—C15B—H15E	109.5
H15A—C15A—H15C	109.5	H15D—C15B—H15F	109.5
H15B—C15A—H15C	109.5	H15E—C15B—H15F	109.5
C4A—C15A—H15A	109.5	C4B—C15B—H15D	109.5
C4A—C15A—H15B	109.5	C4B—C15B—H15E	109.5
C4A—C15A—H15C	109.5	C4B—C15B—H15F	109.5
O3A—C4A—C15A	100 (4)	O3B—C4B—C15B	101 (4)
O3A—C4A—C3A	113 (4)	O3B—C4B—C3B	115 (4)
O1A—C4A—O3A	111 (3)	O1B—C4B—O3B	107 (3)
O1A—C4A—C15A	92 (5)	O1B—C4B—C15B	95 (6)
O1A—C4A—C3A	116 (3)	O1B—C4B—C3B	114 (4)
C15A—C4A—C3A	122 (5)	C15B—C4B—C3B	122 (5)
O3A—C5A—O4A	111 (4)	O3B—C5B—O4B	113 (4)
O3A—C5A—H5A	107.6	O3B—C5B—H5B	104.2
O3A—C5A—C6A	117 (4)	O3B—C5B—C6B	116 (4)
O4A—C5A—H5A	107.6	O4B—C5B—H5B	104.2
O4A—C5A—C6A	106 (3)	O4B—C5B—C6B	113 (4)
C6A—C5A—H5A	107.6	C6B—C5B—H5B	104.2
O2A—C6A—C5A	109 (3)	C12B—C11B—H11B	103.9
O2A—C6A—C1A	102 (3)	C12B—C11B—C13B	112 (4)
O2A—C6A—C7A	109 (3)	C12B—C11B—C7B	110 (4)
C5A—C6A—C1A	107 (4)	C13B—C11B—H11B	103.9
C5A—C6A—C7A	115 (4)	C13B—C11B—C7B	121 (4)
C1A—C6A—C7A	113 (3)	C7B—C11B—H11B	103.9
C6A—C1A—H1A	105.9	O2B—C6B—C5B	107 (3)
C6A—C1A—C10A	107 (4)	O2B—C6B—C1B	102 (4)
C2A—C1A—C6A	112 (4)	O2B—C6B—C7B	104 (4)
C2A—C1A—H1A	105.9	C5B—C6B—C1B	112 (4)
C2A—C1A—C10A	119 (4)	C5B—C6B—C7B	116 (4)
C10A—C1A—H1A	105.9	C1B—C6B—C7B	113 (3)
C1A—C2A—H2AA	105.7	C6B—C1B—H1B	106.7
C1A—C2A—H2AB	105.7	C6B—C1B—C10B	109 (4)
C1A—C2A—C3A	127 (5)	C2B—C1B—C6B	113 (3)
H2AA—C2A—H2AB	106.1	C2B—C1B—H1B	106.7
C3A—C2A—H2AA	105.7	C2B—C1B—C10B	114 (4)
C3A—C2A—H2AB	105.7	C10B—C1B—H1B	106.7
C4A—C3A—C2A	105 (4)	C1B—C2B—H2BA	107.0
C4A—C3A—H3AA	110.7	C1B—C2B—H2BB	107.0
C4A—C3A—H3AB	110.7	C1B—C2B—C3B	121 (5)
C2A—C3A—H3AA	110.7	H2BA—C2B—H2BB	106.8
C2A—C3A—H3AB	110.7	C3B—C2B—H2BA	107.0
H3AA—C3A—H3AB	108.8	C3B—C2B—H2BB	107.0
O4A—C12A—C11A	121 (5)	C4B—C3B—C2B	108 (4)
O5A—C12A—O4A	121 (4)	C4B—C3B—H3BA	110.2
O5A—C12A—C11A	119 (4)	C4B—C3B—H3BB	110.2
C12A—C11A—H11A	106.6	C2B—C3B—H3BA	110.2
C12A—C11A—C13A	116 (5)	C2B—C3B—H3BB	110.2
C12A—C11A—C7A	107 (4)	H3BA—C3B—H3BB	108.5
C13A—C11A—H11A	106.6	O4B—C12B—C11B	122 (5)
C13A—C11A—C7A	114 (4)	O5B—C12B—O4B	117 (4)
C7A—C11A—H11A	106.6	O5B—C12B—C11B	121 (4)
C11A—C13A—H13A	109.5	C11B—C13B—H13D	109.5
C11A—C13A—H13B	109.5	C11B—C13B—H13E	109.5
C11A—C13A—H13C	109.5	C11B—C13B—H13F	109.5
H13A—C13A—H13B	109.5	H13D—C13B—H13E	109.5
H13A—C13A—H13C	109.5	H13D—C13B—H13F	109.5
H13B—C13A—H13C	109.5	H13E—C13B—H13F	109.5
C6A—C7A—C11A	113 (3)	C11B—C7B—H7B	108.3
C6A—C7A—H7A	106.9	C6B—C7B—C11B	111 (4)
C6A—C7A—C8A	115 (4)	C6B—C7B—H7B	108.3
C11A—C7A—H7A	106.9	C6B—C7B—C8B	112 (4)
C11A—C7A—C8A	108 (4)	C8B—C7B—C11B	109 (4)
C8A—C7A—H7A	106.9	C8B—C7B—H7B	108.3
C7A—C8A—H8AA	110.3	C7B—C8B—H8BA	110.6
C7A—C8A—H8AB	110.3	C7B—C8B—H8BB	110.6
H8AA—C8A—H8AB	108.6	H8BA—C8B—H8BB	108.8
C9A—C8A—C7A	107 (4)	C9B—C8B—C7B	106 (4)
C9A—C8A—H8AA	110.3	C9B—C8B—H8BA	110.6
C9A—C8A—H8AB	110.3	C9B—C8B—H8BB	110.6
C8A—C9A—H9AA	109.1	C8B—C9B—H9BA	107.6
C8A—C9A—H9AB	109.1	C8B—C9B—H9BB	107.6
C8A—C9A—C10A	112 (4)	C8B—C9B—C10B	119 (4)
H9AA—C9A—H9AB	107.8	H9BA—C9B—H9BB	107.0
C10A—C9A—H9AA	109.1	C10B—C9B—H9BA	107.6
C10A—C9A—H9AB	109.1	C10B—C9B—H9BB	107.6
C1A—C10A—H10A	106.7	C1B—C10B—H10B	108.5
C9A—C10A—C1A	115 (4)	C9B—C10B—C1B	110 (5)
C9A—C10A—H10A	106.7	C9B—C10B—H10B	108.5
C14A—C10A—C1A	106 (4)	C14B—C10B—C1B	110 (4)
C14A—C10A—C9A	115 (4)	C14B—C10B—C9B	112 (4)
C14A—C10A—H10A	106.7	C14B—C10B—H10B	108.5
C10A—C14A—H14A	109.5	C10B—C14B—H14D	109.5
C10A—C14A—H14B	109.5	C10B—C14B—H14E	109.5
C10A—C14A—H14C	109.5	C10B—C14B—H14F	109.5
H14A—C14A—H14B	109.5	H14D—C14B—H14E	109.5
H14A—C14A—H14C	109.5	H14D—C14B—H14F	109.5
H14B—C14A—H14C	109.5	H14E—C14B—H14F	109.5

O3A—C4A—C3A—C2A	36 (5)	O3B—C4B—C3B—C2B	29 (6)
O3A—C5A—C6A—O2A	−44 (6)	O3B—C5B—C6B—O2B	−53 (7)
O3A—C5A—C6A—C1A	66 (4)	O3B—C5B—C6B—C1B	58 (5)
O3A—C5A—C6A—C7A	−168 (3)	O3B—C5B—C6B—C7B	−169 (3)
O1A—O2A—C6A—C5A	2 (7)	O1B—O2B—C6B—C5B	7 (8)
O1A—O2A—C6A—C1A	−111 (4)	O1B—O2B—C6B—C1B	−111 (5)
O1A—O2A—C6A—C7A	129 (4)	O1B—O2B—C6B—C7B	131 (5)
O1A—C4A—C3A—C2A	−94 (4)	O1B—C4B—C3B—C2B	−95 (5)
O2A—O1A—C4A—O3A	−78 (3)	O2B—O1B—C4B—O3B	−79 (4)
O2A—O1A—C4A—C15A	−179 (5)	O2B—O1B—C4B—C15B	178 (4)
O2A—O1A—C4A—C3A	53 (4)	O2B—O1B—C4B—C3B	49 (4)
O2A—C6A—C1A—C2A	60 (4)	O2B—C6B—C1B—C2B	64 (4)
O2A—C6A—C1A—C10A	−168 (4)	O2B—C6B—C1B—C10B	−168 (4)
O2A—C6A—C7A—C11A	−66 (4)	O2B—C6B—C7B—C11B	−68 (4)
O2A—C6A—C7A—C8A	170 (3)	O2B—C6B—C7B—C8B	170 (4)
O4A—C5A—C6A—O2A	80 (5)	O4B—C5B—C6B—O2B	81 (6)
O4A—C5A—C6A—C1A	−170 (3)	O4B—C5B—C6B—C1B	−168 (3)
O4A—C5A—C6A—C7A	−44 (4)	O4B—C5B—C6B—C7B	−35 (5)
O4A—C12A—C11A—C13A	164 (4)	C15B—C4B—C3B—C2B	152 (5)
O4A—C12A—C11A—C7A	37 (6)	C4B—O3B—C5B—O4B	−103 (4)
O5A—C12A—C11A—C13A	−16 (8)	C4B—O3B—C5B—C6B	31 (5)
O5A—C12A—C11A—C7A	−144 (5)	C4B—O1B—O2B—C6B	54 (6)
C15A—C4A—C3A—C2A	155 (5)	C5B—O3B—C4B—O1B	35 (4)
C4A—O3A—C5A—O4A	−97 (4)	C5B—O3B—C4B—C15B	134 (6)
C4A—O3A—C5A—C6A	25 (5)	C5B—O3B—C4B—C3B	−93 (4)
C4A—O1A—O2A—C6A	54 (5)	C5B—O4B—C12B—O5B	160 (4)
C5A—O3A—C4A—O1A	37 (4)	C5B—O4B—C12B—C11B	−26 (7)
C5A—O3A—C4A—C15A	134 (5)	C5B—C6B—C1B—C2B	−50 (4)
C5A—O3A—C4A—C3A	−95 (4)	C5B—C6B—C1B—C10B	78 (4)
C5A—O4A—C12A—O5A	148 (5)	C5B—C6B—C7B—C11B	50 (4)
C5A—O4A—C12A—C11A	−32 (7)	C5B—C6B—C7B—C8B	−72 (4)
C5A—C6A—C1A—C2A	−55 (4)	C11B—C7B—C8B—C9B	−177 (4)
C5A—C6A—C1A—C10A	77 (4)	C6B—C1B—C2B—C3B	−37 (6)
C5A—C6A—C7A—C11A	57 (4)	C6B—C1B—C10B—C9B	51 (5)
C5A—C6A—C7A—C8A	−67 (4)	C6B—C1B—C10B—C14B	174 (4)
C6A—C1A—C2A—C3A	−32 (6)	C6B—C7B—C8B—C9B	−54 (4)
C6A—C1A—C10A—C9A	53 (5)	C1B—C6B—C7B—C11B	−178 (3)
C6A—C1A—C10A—C14A	−179 (4)	C1B—C6B—C7B—C8B	60 (4)
C6A—C7A—C8A—C9A	−55 (5)	C1B—C2B—C3B—C4B	55 (6)
C1A—C6A—C7A—C11A	−179 (3)	C2B—C1B—C10B—C9B	179 (4)
C1A—C6A—C7A—C8A	56 (4)	C2B—C1B—C10B—C14B	−58 (5)
C1A—C2A—C3A—C4A	49 (6)	C12B—O4B—C5B—O3B	158 (3)
C2A—C1A—C10A—C9A	−179 (4)	C12B—O4B—C5B—C6B	23 (6)
C2A—C1A—C10A—C14A	−51 (5)	C12B—C11B—C7B—C6B	−48 (4)
C12A—O4A—C5A—O3A	160 (4)	C12B—C11B—C7B—C8B	76 (5)
C12A—O4A—C5A—C6A	33 (6)	C13B—C11B—C12B—O4B	176 (4)
C12A—C11A—C7A—C6A	−48 (5)	C13B—C11B—C12B—O5B	−10 (6)
C12A—C11A—C7A—C8A	79 (5)	C13B—C11B—C7B—C6B	179 (3)
C11A—C7A—C8A—C9A	178 (4)	C13B—C11B—C7B—C8B	−57 (5)
C13A—C11A—C7A—C6A	−178 (3)	C7B—C11B—C12B—O4B	38 (5)
C13A—C11A—C7A—C8A	−50 (5)	C7B—C11B—C12B—O5B	−148 (4)
C7A—C6A—C1A—C2A	177 (3)	C7B—C6B—C1B—C2B	176 (3)
C7A—C6A—C1A—C10A	−51 (4)	C7B—C6B—C1B—C10B	−57 (4)
C7A—C8A—C9A—C10A	54 (5)	C7B—C8B—C9B—C10B	54 (6)
C8A—C9A—C10A—C1A	−57 (5)	C8B—C9B—C10B—C1B	−54 (6)
C8A—C9A—C10A—C14A	179 (3)	C8B—C9B—C10B—C14B	−176 (4)
C10A—C1A—C2A—C3A	−158 (5)	C10B—C1B—C2B—C3B	−162 (4)

Artemisinin (FormIII_3) top

Crystal data top

C₁₅H₂₂O₅	F(000) = 608
M_r = 282.32	D_x = 1.620 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 9.1432 (14) Å	Cell parameters from 866 reflections
b = 13.835 (2) Å	θ = 2.7–23.1°
c = 9.459 (4) Å	µ = 0.12 mm⁻¹
β = 104.69 (3)°	T = 296 K
V = 1157.5 (6) Å³	Prism, clear colourless
Z = 4	0.2 × 0.1 × 0.09 mm

Data collection top

Bruker D8 Venture diffractometer	1210 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	651 reflections with I > 2σ(I)
Mirror optics monochromator	R_int = 0.108
ω scans	θ_max = 23.3°, θ_min = 2.3°
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0846 before and 0.0635 after correction. The Ratio of minimum to maximum transmission is 0.8715. The λ/2 correction factor is Not present.	h = −10→10
T_min = 0.649, T_max = 0.745	k = −15→14
5284 measured reflections	l = −4→4

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.063	w = 1/[σ²(F_o²) + (0.0444P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.123	(Δ/σ)_max < 0.001
S = 1.00	Δρ_max = 0.20 e Å⁻³
1210 reflections	Δρ_min = −0.17 e Å⁻³
167 parameters	Absolute structure: Flack x determined using 222 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
47 restraints	Absolute structure parameter: −0.3 (10)

Special details top

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

	x	y	z	U_iso*/U_eq
O3A	0.7967 (11)	0.3110 (8)	0.721 (3)	0.031 (4)*
O1A	1.0239 (12)	0.2287 (7)	0.807 (2)	0.032 (4)*
O2A	1.1129 (10)	0.3146 (6)	0.862 (3)	0.024 (3)*
O4A	0.8310 (11)	0.3095 (8)	0.968 (3)	0.026 (4)*
O5A	0.8495 (12)	0.3096 (8)	1.208 (3)	0.036 (4)*
C15A	0.836 (2)	0.1615 (12)	0.618 (5)	0.044 (6)*
H15A	0.796018	0.130148	0.690813	0.065*
H15B	0.908350	0.119870	0.591042	0.065*
H15C	0.755062	0.175115	0.533553	0.065*
C4A	0.9122 (16)	0.2552 (10)	0.679 (2)	0.027 (6)*
C5A	0.8507 (14)	0.3672 (12)	0.847 (3)	0.022 (6)*
H5A	0.788191	0.425400	0.839559	0.027*
C6A	1.0154 (14)	0.3976 (9)	0.863 (3)	0.020 (5)*
C1A	1.022 (2)	0.4653 (11)	0.737 (4)	0.029 (5)*
H1A	1.129103	0.480170	0.746911	0.035*
C2A	0.961 (2)	0.4242 (10)	0.583 (4)	0.043 (7)*
H2AA	1.015113	0.454564	0.519100	0.051*
H2AB	0.855687	0.442334	0.549131	0.051*
C3A	0.9732 (17)	0.3135 (10)	0.568 (3)	0.023 (5)*
H3AA	0.917989	0.294734	0.470671	0.028*
H3AB	1.078490	0.296553	0.579778	0.028*
C12A	0.9057 (17)	0.3297 (12)	1.107 (3)	0.034 (7)*
C11A	1.0656 (17)	0.3721 (13)	1.136 (3)	0.031 (6)*
H11A	1.132021	0.317418	1.130380	0.037*
C13A	1.117 (2)	0.4096 (14)	1.292 (4)	0.045 (7)*
H13A	1.045123	0.455674	1.309681	0.068*
H13B	1.214164	0.440218	1.306681	0.068*
H13C	1.124981	0.356645	1.359456	0.068*
C7A	1.0800 (19)	0.4417 (10)	1.014 (3)	0.022 (5)*
H7A	1.187750	0.454317	1.024512	0.027*
C8A	1.004 (2)	0.5376 (9)	1.034 (4)	0.028 (6)*
H8AA	0.900880	0.525526	1.040093	0.033*
H8AB	1.058198	0.567944	1.124575	0.033*
C9A	1.002 (2)	0.6047 (12)	0.906 (3)	0.026 (6)*
H9AA	0.940427	0.660544	0.914186	0.031*
H9AB	1.104226	0.627557	0.915320	0.031*
C10A	0.943 (2)	0.5618 (10)	0.754 (3)	0.029 (5)*
H10A	0.836234	0.546994	0.743194	0.035*
C14A	0.9507 (17)	0.6337 (12)	0.633 (4)	0.028 (6)*
H14A	1.054419	0.644777	0.633423	0.043*
H14B	0.905058	0.693676	0.650178	0.043*
H14C	0.897333	0.607793	0.540422	0.043*
O3B	0.3099 (12)	0.0054 (8)	0.718 (3)	0.029 (4)*
O1B	0.5598 (13)	−0.0404 (7)	0.801 (3)	0.034 (4)*
O2B	0.6208 (10)	0.0578 (7)	0.838 (3)	0.022 (3)*
O4B	0.3507 (13)	0.0138 (9)	0.967 (3)	0.031 (4)*
O5B	0.3873 (13)	0.0150 (9)	1.206 (3)	0.038 (4)*
C15B	0.4053 (17)	−0.1336 (10)	0.629 (5)	0.031 (5)*
H15D	0.349647	−0.163451	0.691030	0.047*
H15E	0.498501	−0.167772	0.637771	0.047*
H15F	0.346377	−0.135587	0.529622	0.047*
C4B	0.4387 (17)	−0.0300 (10)	0.675 (3)	0.024 (5)*
C5B	0.3518 (16)	0.0684 (13)	0.837 (3)	0.034 (6)*
H5B	0.271047	0.116615	0.825269	0.041*
C11B	0.5744 (18)	0.0949 (11)	1.114 (3)	0.024 (6)*
H11B	0.649038	0.048567	1.096583	0.028*
C6B	0.4972 (15)	0.1238 (9)	0.845 (3)	0.016 (5)*
C1B	0.4831 (17)	0.1925 (10)	0.717 (3)	0.014 (5)*
H1B	0.584253	0.217648	0.721108	0.017*
C2B	0.4244 (19)	0.1444 (9)	0.569 (3)	0.033 (6)*
H2BA	0.459707	0.181159	0.497071	0.040*
H2BB	0.314841	0.147913	0.542930	0.040*
C3B	0.4705 (18)	0.0386 (8)	0.560 (4)	0.029 (6)*
H3BA	0.418667	0.014093	0.464318	0.035*
H3BB	0.578087	0.036787	0.566442	0.035*
C12B	0.4291 (19)	0.0392 (12)	1.100 (3)	0.037 (7)*
C13B	0.6329 (19)	0.1304 (12)	1.270 (4)	0.026 (5)*
H13D	0.554922	0.166222	1.298280	0.039*
H13E	0.719094	0.171398	1.276505	0.039*
H13F	0.661792	0.076070	1.334254	0.039*
C7B	0.5531 (16)	0.1709 (10)	0.993 (3)	0.014 (5)*
H7B	0.652688	0.198717	0.997577	0.017*
C8B	0.4486 (18)	0.2545 (10)	1.013 (3)	0.029 (5)*
H8BA	0.348781	0.230068	1.011196	0.035*
H8BB	0.489291	0.286723	1.105497	0.035*
C9B	0.4394 (17)	0.3248 (11)	0.887 (3)	0.028 (6)*
H9BA	0.538962	0.352084	0.894853	0.033*
H9BB	0.372206	0.377470	0.895666	0.033*
C10B	0.3832 (18)	0.2786 (11)	0.737 (3)	0.031 (6)*
H10B	0.280367	0.254648	0.727585	0.037*
C14B	0.3773 (16)	0.3531 (13)	0.616 (4)	0.036 (6)*
H14D	0.478248	0.372419	0.616413	0.054*
H14E	0.320820	0.408477	0.632761	0.054*
H14F	0.329180	0.325032	0.522970	0.054*

Geometric parameters (Å, º) top

O3A—C4A	1.439 (13)	O3B—C4B	1.427 (12)
O3A—C5A	1.406 (14)	O3B—C5B	1.399 (14)
O1A—O2A	1.460 (12)	O1B—O2B	1.477 (11)
O1A—C4A	1.417 (14)	O1B—C4B	1.411 (14)
O2A—C6A	1.455 (11)	O2B—C6B	1.467 (12)
O4A—C5A	1.445 (14)	O4B—C5B	1.440 (14)
O4A—C12A	1.350 (14)	O4B—C12B	1.334 (14)
O5A—C12A	1.219 (14)	O5B—C12B	1.201 (14)
C15A—H15A	0.9600	C15B—H15D	0.9600
C15A—H15B	0.9600	C15B—H15E	0.9600
C15A—H15C	0.9600	C15B—H15F	0.9600
C15A—C4A	1.516 (14)	C15B—C4B	1.506 (13)
C4A—C3A	1.536 (14)	C4B—C3B	1.529 (15)
C5A—H5A	0.9800	C5B—H5B	0.9800
C5A—C6A	1.534 (13)	C5B—C6B	1.520 (13)
C6A—C1A	1.531 (14)	C11B—H11B	0.9800
C6A—C7A	1.526 (15)	C11B—C12B	1.513 (13)
C1A—H1A	0.9800	C11B—C13B	1.519 (15)
C1A—C2A	1.524 (15)	C11B—C7B	1.528 (14)
C1A—C10A	1.547 (13)	C6B—C1B	1.516 (14)
C2A—H2AA	0.9700	C6B—C7B	1.517 (14)
C2A—H2AB	0.9700	C1B—H1B	0.9800
C2A—C3A	1.545 (13)	C1B—C2B	1.518 (15)
C3A—H3AA	0.9700	C1B—C10B	1.541 (13)
C3A—H3AB	0.9700	C2B—H2BA	0.9700
C12A—C11A	1.534 (13)	C2B—H2BB	0.9700
C11A—H11A	0.9800	C2B—C3B	1.531 (13)
C11A—C13A	1.527 (15)	C3B—H3BA	0.9700
C11A—C7A	1.535 (14)	C3B—H3BB	0.9700
C13A—H13A	0.9600	C13B—H13D	0.9600
C13A—H13B	0.9600	C13B—H13E	0.9600
C13A—H13C	0.9600	C13B—H13F	0.9600
C7A—H7A	0.9800	C7B—H7B	0.9800
C7A—C8A	1.535 (12)	C7B—C8B	1.541 (13)
C8A—H8AA	0.9700	C8B—H8BA	0.9700
C8A—H8AB	0.9700	C8B—H8BB	0.9700
C8A—C9A	1.522 (15)	C8B—C9B	1.523 (15)
C9A—H9AA	0.9700	C9B—H9BA	0.9700
C9A—H9AB	0.9700	C9B—H9BB	0.9700
C9A—C10A	1.519 (15)	C9B—C10B	1.525 (15)
C10A—H10A	0.9800	C10B—H10B	0.9800
C10A—C14A	1.532 (15)	C10B—C14B	1.528 (15)
C14A—H14A	0.9600	C14B—H14D	0.9600
C14A—H14B	0.9600	C14B—H14E	0.9600
C14A—H14C	0.9600	C14B—H14F	0.9600

C5A—O3A—C4A	113.8 (12)	C5B—O3B—C4B	111.4 (14)
C4A—O1A—O2A	108.1 (12)	C4B—O1B—O2B	105.8 (13)
C6A—O2A—O1A	110.9 (10)	C6B—O2B—O1B	109.5 (9)
C12A—O4A—C5A	121.8 (13)	C12B—O4B—C5B	123.4 (14)
H15A—C15A—H15B	109.5	H15D—C15B—H15E	109.5
H15A—C15A—H15C	109.5	H15D—C15B—H15F	109.5
H15B—C15A—H15C	109.5	H15E—C15B—H15F	109.5
C4A—C15A—H15A	109.5	C4B—C15B—H15D	109.5
C4A—C15A—H15B	109.5	C4B—C15B—H15E	109.5
C4A—C15A—H15C	109.5	C4B—C15B—H15F	109.5
O3A—C4A—C15A	105.4 (13)	O3B—C4B—C15B	106.7 (13)
O3A—C4A—C3A	108.7 (14)	O3B—C4B—C3B	108.0 (14)
O1A—C4A—O3A	109.1 (14)	O1B—C4B—O3B	108.9 (15)
O1A—C4A—C15A	105.5 (18)	O1B—C4B—C15B	101.8 (18)
O1A—C4A—C3A	114.2 (13)	O1B—C4B—C3B	114.5 (14)
C15A—C4A—C3A	113.5 (18)	C15B—C4B—C3B	116.5 (18)
O3A—C5A—O4A	106.4 (14)	O3B—C5B—O4B	107.3 (16)
O3A—C5A—H5A	108.8	O3B—C5B—H5B	106.7
O3A—C5A—C6A	111.1 (15)	O3B—C5B—C6B	114.2 (17)
O4A—C5A—H5A	108.8	O4B—C5B—H5B	106.7
O4A—C5A—C6A	112.9 (15)	O4B—C5B—C6B	114.8 (16)
C6A—C5A—H5A	108.8	C6B—C5B—H5B	106.7
O2A—C6A—C5A	111.7 (11)	C12B—C11B—H11B	106.7
O2A—C6A—C1A	109.4 (16)	C12B—C11B—C13B	109.4 (18)
O2A—C6A—C7A	103.1 (16)	C12B—C11B—C7B	110.1 (17)
C1A—C6A—C5A	108.9 (15)	C13B—C11B—H11B	106.7
C7A—C6A—C5A	109.9 (18)	C13B—C11B—C7B	116.8 (15)
C7A—C6A—C1A	113.8 (14)	C7B—C11B—H11B	106.7
C6A—C1A—H1A	106.7	O2B—C6B—C5B	111.1 (12)
C6A—C1A—C10A	109.3 (16)	O2B—C6B—C1B	105.4 (15)
C2A—C1A—C6A	115.9 (16)	O2B—C6B—C7B	103.1 (16)
C2A—C1A—H1A	106.7	C1B—C6B—C5B	112.5 (17)
C2A—C1A—C10A	111.0 (18)	C1B—C6B—C7B	114.2 (13)
C10A—C1A—H1A	106.7	C7B—C6B—C5B	110.1 (18)
C1A—C2A—H2AA	108.3	C6B—C1B—H1B	107.6
C1A—C2A—H2AB	108.3	C6B—C1B—C2B	113.4 (14)
C1A—C2A—C3A	116 (2)	C6B—C1B—C10B	108.8 (15)
H2AA—C2A—H2AB	107.4	C2B—C1B—H1B	107.6
C3A—C2A—H2AA	108.3	C2B—C1B—C10B	111.6 (16)
C3A—C2A—H2AB	108.3	C10B—C1B—H1B	107.6
C4A—C3A—C2A	114.3 (17)	C1B—C2B—H2BA	108.4
C4A—C3A—H3AA	108.7	C1B—C2B—H2BB	108.4
C4A—C3A—H3AB	108.7	C1B—C2B—C3B	116 (2)
C2A—C3A—H3AA	108.7	H2BA—C2B—H2BB	107.4
C2A—C3A—H3AB	108.7	C3B—C2B—H2BA	108.4
H3AA—C3A—H3AB	107.6	C3B—C2B—H2BB	108.4
O4A—C12A—C11A	118.3 (19)	C4B—C3B—C2B	116.6 (18)
O5A—C12A—O4A	120.2 (16)	C4B—C3B—H3BA	108.1
O5A—C12A—C11A	121.4 (19)	C4B—C3B—H3BB	108.1
C12A—C11A—H11A	105.7	C2B—C3B—H3BA	108.1
C12A—C11A—C7A	111.5 (18)	C2B—C3B—H3BB	108.1
C13A—C11A—C12A	110.3 (18)	H3BA—C3B—H3BB	107.3
C13A—C11A—H11A	105.7	O4B—C12B—C11B	118 (2)
C13A—C11A—C7A	116.9 (16)	O5B—C12B—O4B	120.4 (17)
C7A—C11A—H11A	105.7	O5B—C12B—C11B	122 (2)
C11A—C13A—H13A	109.5	C11B—C13B—H13D	109.5
C11A—C13A—H13B	109.5	C11B—C13B—H13E	109.5
C11A—C13A—H13C	109.5	C11B—C13B—H13F	109.5
H13A—C13A—H13B	109.5	H13D—C13B—H13E	109.5
H13A—C13A—H13C	109.5	H13D—C13B—H13F	109.5
H13B—C13A—H13C	109.5	H13E—C13B—H13F	109.5
C6A—C7A—C11A	111.5 (15)	C11B—C7B—H7B	107.3
C6A—C7A—H7A	108.0	C11B—C7B—C8B	113.1 (16)
C6A—C7A—C8A	112.5 (17)	C6B—C7B—C11B	110.3 (14)
C11A—C7A—H7A	108.0	C6B—C7B—H7B	107.3
C8A—C7A—C11A	108.6 (16)	C6B—C7B—C8B	111.1 (16)
C8A—C7A—H7A	108.0	C8B—C7B—H7B	107.3
C7A—C8A—H8AA	109.7	C7B—C8B—H8BA	110.2
C7A—C8A—H8AB	109.7	C7B—C8B—H8BB	110.2
H8AA—C8A—H8AB	108.2	H8BA—C8B—H8BB	108.5
C9A—C8A—C7A	109.9 (17)	C9B—C8B—C7B	107.4 (16)
C9A—C8A—H8AA	109.7	C9B—C8B—H8BA	110.2
C9A—C8A—H8AB	109.7	C9B—C8B—H8BB	110.2
C8A—C9A—H9AA	108.2	C8B—C9B—H9BA	108.9
C8A—C9A—H9AB	108.2	C8B—C9B—H9BB	108.9
H9AA—C9A—H9AB	107.4	C8B—C9B—C10B	113.6 (15)
C10A—C9A—C8A	116.3 (15)	H9BA—C9B—H9BB	107.7
C10A—C9A—H9AA	108.2	C10B—C9B—H9BA	108.9
C10A—C9A—H9AB	108.2	C10B—C9B—H9BB	108.9
C1A—C10A—H10A	106.7	C1B—C10B—H10B	108.2
C9A—C10A—C1A	112.2 (19)	C9B—C10B—C1B	111.5 (17)
C9A—C10A—H10A	106.7	C9B—C10B—H10B	108.2
C9A—C10A—C14A	112.4 (16)	C9B—C10B—C14B	110.7 (16)
C14A—C10A—C1A	111.7 (17)	C14B—C10B—C1B	109.9 (17)
C14A—C10A—H10A	106.7	C14B—C10B—H10B	108.2
C10A—C14A—H14A	109.5	C10B—C14B—H14D	109.5
C10A—C14A—H14B	109.5	C10B—C14B—H14E	109.5
C10A—C14A—H14C	109.5	C10B—C14B—H14F	109.5
H14A—C14A—H14B	109.5	H14D—C14B—H14E	109.5
H14A—C14A—H14C	109.5	H14D—C14B—H14F	109.5
H14B—C14A—H14C	109.5	H14E—C14B—H14F	109.5

O3A—C4A—C3A—C2A	28 (2)	O3B—C4B—C3B—C2B	29 (2)
O3A—C5A—C6A—O2A	−56 (3)	O3B—C5B—C6B—O2B	−53 (3)
O3A—C5A—C6A—C1A	65.4 (17)	O3B—C5B—C6B—C1B	65 (2)
O3A—C5A—C6A—C7A	−169.4 (12)	O3B—C5B—C6B—C7B	−166.5 (14)
O1A—O2A—C6A—C5A	16 (3)	O1B—O2B—C6B—C5B	9 (3)
O1A—O2A—C6A—C1A	−105.1 (18)	O1B—O2B—C6B—C1B	−112.7 (18)
O1A—O2A—C6A—C7A	133.5 (16)	O1B—O2B—C6B—C7B	127.3 (17)
O1A—C4A—C3A—C2A	−94.3 (18)	O1B—C4B—C3B—C2B	−92.3 (19)
O2A—O1A—C4A—O3A	−73.5 (15)	O2B—O1B—C4B—O3B	−78.5 (14)
O2A—O1A—C4A—C15A	173.7 (14)	O2B—O1B—C4B—C15B	169.0 (17)
O2A—O1A—C4A—C3A	48.3 (15)	O2B—O1B—C4B—C3B	42.5 (16)
O2A—C6A—C1A—C2A	64.3 (17)	O2B—C6B—C1B—C2B	68.6 (17)
O2A—C6A—C1A—C10A	−169.4 (17)	O2B—C6B—C1B—C10B	−166.6 (15)
O2A—C6A—C7A—C11A	−63.5 (17)	O2B—C6B—C7B—C11B	−62.2 (13)
O2A—C6A—C7A—C8A	174.3 (14)	O2B—C6B—C7B—C8B	171.6 (13)
O4A—C5A—C6A—O2A	64 (3)	O4B—C5B—C6B—O2B	72 (3)
O4A—C5A—C6A—C1A	−175.1 (13)	O4B—C5B—C6B—C1B	−170.6 (14)
O4A—C5A—C6A—C7A	−49.9 (16)	O4B—C5B—C6B—C7B	−42.0 (19)
O4A—C12A—C11A—C13A	167.9 (16)	C15B—C4B—C3B—C2B	149.1 (19)
O4A—C12A—C11A—C7A	36 (2)	C4B—O3B—C5B—O4B	−98.9 (15)
O5A—C12A—C11A—C13A	−16 (3)	C4B—O3B—C5B—C6B	30 (2)
O5A—C12A—C11A—C7A	−147.6 (18)	C4B—O1B—O2B—C6B	51 (2)
C15A—C4A—C3A—C2A	144.7 (18)	C5B—O3B—C4B—O1B	34.2 (18)
C4A—O3A—C5A—O4A	−93.4 (15)	C5B—O3B—C4B—C15B	143 (2)
C4A—O3A—C5A—C6A	29.9 (19)	C5B—O3B—C4B—C3B	−90.7 (18)
C4A—O1A—O2A—C6A	46 (2)	C5B—O4B—C12B—O5B	153.5 (15)
C5A—O3A—C4A—O1A	31.7 (16)	C5B—O4B—C12B—C11B	−29 (2)
C5A—O3A—C4A—C15A	144.6 (19)	C5B—C6B—C1B—C2B	−52.5 (18)
C5A—O3A—C4A—C3A	−93.4 (17)	C5B—C6B—C1B—C10B	72.3 (18)
C5A—O4A—C12A—O5A	150.5 (15)	C5B—C6B—C7B—C11B	56.4 (16)
C5A—O4A—C12A—C11A	−33 (2)	C5B—C6B—C7B—C8B	−69.9 (16)
C5A—C6A—C1A—C2A	−58.1 (19)	C11B—C7B—C8B—C9B	179.3 (14)
C5A—C6A—C1A—C10A	68.2 (18)	C6B—C1B—C2B—C3B	−33 (2)
C5A—C6A—C7A—C11A	55.8 (16)	C6B—C1B—C10B—C9B	52.3 (19)
C5A—C6A—C7A—C8A	−66.5 (17)	C6B—C1B—C10B—C14B	175.5 (14)
C6A—C1A—C2A—C3A	−29 (2)	C6B—C7B—C8B—C9B	−56.1 (17)
C6A—C1A—C10A—C9A	51 (2)	C1B—C6B—C7B—C11B	−175.9 (11)
C6A—C1A—C10A—C14A	178.3 (15)	C1B—C6B—C7B—C8B	57.8 (16)
C6A—C7A—C8A—C9A	−50.4 (18)	C1B—C2B—C3B—C4B	52 (2)
C1A—C6A—C7A—C11A	178.1 (11)	C2B—C1B—C10B—C9B	178.2 (14)
C1A—C6A—C7A—C8A	55.8 (18)	C2B—C1B—C10B—C14B	−59 (2)
C1A—C2A—C3A—C4A	50 (2)	C12B—O4B—C5B—O3B	157.4 (14)
C2A—C1A—C10A—C9A	−179.9 (15)	C12B—O4B—C5B—C6B	29 (2)
C2A—C1A—C10A—C14A	−53 (2)	C12B—C11B—C7B—C6B	−55.5 (18)
C12A—O4A—C5A—O3A	162.2 (12)	C12B—C11B—C7B—C8B	70 (2)
C12A—O4A—C5A—C6A	40 (2)	C13B—C11B—C12B—O4B	171.1 (15)
C12A—C11A—C7A—C6A	−48 (2)	C13B—C11B—C12B—O5B	−12 (2)
C12A—C11A—C7A—C8A	76.4 (19)	C13B—C11B—C7B—C6B	178.9 (13)
C11A—C7A—C8A—C9A	−174.3 (14)	C13B—C11B—C7B—C8B	−56 (2)
C13A—C11A—C7A—C6A	−176.4 (13)	C7B—C11B—C12B—O4B	41 (2)
C13A—C11A—C7A—C8A	−52 (2)	C7B—C11B—C12B—O5B	−141.3 (18)
C7A—C6A—C1A—C2A	179.1 (13)	C7B—C6B—C1B—C2B	−179.0 (12)
C7A—C6A—C1A—C10A	−54.7 (19)	C7B—C6B—C1B—C10B	−54.2 (18)
C7A—C8A—C9A—C10A	50 (2)	C7B—C8B—C9B—C10B	57 (2)
C8A—C9A—C10A—C1A	−51 (2)	C8B—C9B—C10B—C1B	−57 (2)
C8A—C9A—C10A—C14A	−178.2 (12)	C8B—C9B—C10B—C14B	−179.8 (12)
C10A—C1A—C2A—C3A	−154.1 (15)	C10B—C1B—C2B—C3B	−156.2 (15)

Artemisinin (FormIII_4) top

Crystal data top

C₁₅H₂₂O₅	F(000) = 602
M_r = 280.81	D_x = 1.637 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 9.076 (2) Å	Cell parameters from 527 reflections
b = 13.755 (4) Å	θ = 2.8–21.1°
c = 9.428 (7) Å	µ = 0.12 mm⁻¹
β = 104.60 (4)°	T = 296 K
V = 1139.1 (9) Å³	Prism, clear colourless
Z = 4	0.2 × 0.1 × 0.09 mm

Data collection top

Bruker D8 Venture diffractometer	1265 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	439 reflections with I > 2σ(I)
Mirror optics monochromator	R_int = 0.328
ω scans	θ_max = 23.4°, θ_min = 2.3°
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1441 before and 0.0799 after correction. The Ratio of minimum to maximum transmission is 0.4811. The λ/2 correction factor is Not present.	h = −10→10
T_min = 0.358, T_max = 0.745	k = −15→15
6090 measured reflections	l = −4→4

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.151	w = 1/[σ²(F_o²) + (0.1133P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.286	(Δ/σ)_max < 0.001
S = 1.01	Δρ_max = 0.24 e Å⁻³
1265 reflections	Δρ_min = −0.34 e Å⁻³
167 parameters	Absolute structure: Flack x determined using 119 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
47 restraints	Absolute structure parameter: −1.8 (10)

Special details top

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

	x	y	z	U_iso*/U_eq
O3A	0.796 (2)	0.3130 (16)	0.723 (5)	0.019 (7)*
O1A	1.022 (3)	0.2271 (17)	0.810 (5)	0.035 (8)*
O2A	1.117 (2)	0.3123 (14)	0.866 (6)	0.032 (7)*
O4A	0.832 (3)	0.310 (2)	0.969 (6)	0.040 (9)*
O5A	0.847 (3)	0.3120 (18)	1.209 (6)	0.045 (8)*
C15A	0.836 (4)	0.162 (2)	0.626 (11)	0.051 (14)*
H15A	0.762766	0.146296	0.680840	0.076*
H15B	0.910692	0.111154	0.639086	0.076*
H15C	0.784976	0.167746	0.524244	0.076*
C4A	0.913 (3)	0.257 (2)	0.681 (5)	0.033 (13)*
C5A	0.850 (3)	0.370 (2)	0.848 (5)	0.017 (12)*
H5A	0.789047	0.429362	0.842027	0.021*
C6A	1.017 (3)	0.3958 (18)	0.859 (7)	0.020 (11)*
C1A	1.026 (4)	0.467 (2)	0.737 (7)	0.021 (11)*
H1A	1.133725	0.480782	0.744440	0.026*
C2A	0.957 (5)	0.425 (2)	0.584 (8)	0.048 (15)*
H2AA	1.002974	0.457216	0.514940	0.058*
H2AB	0.848927	0.440444	0.557114	0.058*
C3A	0.975 (4)	0.315 (2)	0.570 (6)	0.027 (11)*
H3AA	0.921298	0.294907	0.471401	0.032*
H3AB	1.081688	0.299656	0.582939	0.032*
C12A	0.906 (4)	0.328 (3)	1.110 (6)	0.033 (16)*
C11A	1.067 (4)	0.367 (3)	1.133 (7)	0.040 (15)*
H11A	1.134234	0.312509	1.126687	0.048*
C13A	1.115 (4)	0.408 (3)	1.288 (7)	0.046 (15)*
H13A	1.027491	0.431818	1.316754	0.068*
H13B	1.185997	0.460509	1.291245	0.068*
H13C	1.163211	0.357885	1.354846	0.068*
C7A	1.075 (5)	0.441 (2)	1.012 (6)	0.038 (13)*
H7A	1.183568	0.454318	1.023390	0.046*
C8A	1.001 (5)	0.538 (2)	1.033 (7)	0.035 (14)*
H8AA	0.896701	0.527221	1.037439	0.041*
H8AB	1.055717	0.567701	1.124139	0.041*
C9A	1.002 (4)	0.607 (3)	0.906 (7)	0.030 (13)*
H9AA	1.105808	0.629692	0.917279	0.036*
H9AB	0.939919	0.662721	0.913147	0.036*
C10A	0.946 (4)	0.563 (2)	0.753 (7)	0.027 (11)*
H10A	0.838994	0.547113	0.741937	0.033*
C14A	0.948 (4)	0.638 (3)	0.633 (8)	0.047 (15)*
H14A	1.050720	0.649921	0.628479	0.070*
H14B	0.903190	0.697888	0.654821	0.070*
H14C	0.889963	0.613812	0.540040	0.070*
O3B	0.311 (3)	0.006 (2)	0.714 (6)	0.044 (9)*
O1B	0.561 (3)	−0.0398 (16)	0.800 (6)	0.042 (9)*
O2B	0.623 (3)	0.0597 (16)	0.832 (6)	0.033 (8)*
O4B	0.350 (3)	0.008 (2)	0.959 (7)	0.047 (10)*
O5B	0.389 (3)	0.013 (2)	1.203 (8)	0.047 (10)*
C15B	0.410 (4)	−0.138 (2)	0.641 (12)	0.034 (12)*
H15D	0.365001	−0.164253	0.714349	0.051*
H15E	0.503356	−0.170889	0.643315	0.051*
H15F	0.340809	−0.145517	0.546027	0.051*
C4B	0.442 (4)	−0.031 (2)	0.671 (6)	0.031 (13)*
C5B	0.349 (4)	0.069 (3)	0.835 (6)	0.045 (14)*
H5B	0.267803	0.117424	0.825130	0.054*
C11B	0.575 (4)	0.090 (3)	1.110 (7)	0.032 (13)*
H11B	0.649472	0.043653	1.091947	0.039*
C6B	0.500 (3)	0.1232 (17)	0.849 (6)	0.008 (10)*
C1B	0.484 (4)	0.193 (2)	0.720 (7)	0.027 (12)*
H1B	0.585789	0.218878	0.723386	0.033*
C2B	0.425 (4)	0.144 (2)	0.571 (7)	0.032 (13)*
H2BA	0.458486	0.182822	0.498570	0.038*
H2BB	0.315075	0.146761	0.546198	0.038*
C3B	0.472 (5)	0.0386 (19)	0.554 (7)	0.040 (15)*
H3BA	0.579577	0.036929	0.557635	0.048*
H3BB	0.416884	0.015261	0.458122	0.048*
C12B	0.424 (4)	0.038 (3)	1.094 (8)	0.047 (18)*
C13B	0.633 (4)	0.130 (3)	1.265 (7)	0.032 (13)*
H13D	0.551289	0.162770	1.293884	0.048*
H13E	0.714080	0.175214	1.267658	0.048*
H13F	0.669363	0.077533	1.331654	0.048*
C7B	0.558 (4)	0.173 (2)	0.998 (6)	0.030 (12)*
H7B	0.658802	0.201128	1.002979	0.036*
C8B	0.449 (4)	0.256 (2)	1.015 (8)	0.032 (12)*
H8BA	0.348504	0.229709	1.011481	0.039*
H8BB	0.486597	0.289002	1.107447	0.039*
C9B	0.441 (4)	0.325 (3)	0.887 (7)	0.043 (14)*
H9BA	0.541706	0.351149	0.893975	0.051*
H9BB	0.375191	0.379528	0.896242	0.051*
C10B	0.381 (5)	0.279 (2)	0.737 (7)	0.042 (14)*
H10B	0.278564	0.253522	0.730386	0.050*
C14B	0.371 (5)	0.354 (3)	0.616 (8)	0.046 (14)*
H14D	0.463952	0.390586	0.634325	0.069*
H14E	0.287522	0.397661	0.614481	0.069*
H14F	0.354211	0.322028	0.522906	0.069*

Geometric parameters (Å, º) top

O3A—C4A	1.442 (15)	O3B—C4B	1.438 (15)
O3A—C5A	1.401 (16)	O3B—C5B	1.403 (16)
O1A—O2A	1.474 (15)	O1B—O2B	1.482 (14)
O1A—C4A	1.423 (16)	O1B—C4B	1.419 (16)
O2A—C6A	1.459 (15)	O2B—C6B	1.462 (15)
O4A—C5A	1.447 (15)	O4B—C5B	1.445 (16)
O4A—C12A	1.349 (16)	O4B—C12B	1.341 (16)
O5A—C12A	1.212 (15)	O5B—C12B	1.206 (16)
C15A—H15A	0.9600	C15B—H15D	0.9600
C15A—H15B	0.9600	C15B—H15E	0.9600
C15A—H15C	0.9600	C15B—H15F	0.9600
C15A—C4A	1.511 (15)	C15B—C4B	1.512 (15)
C4A—C3A	1.532 (16)	C4B—C3B	1.532 (16)
C5A—H5A	0.9800	C5B—H5B	0.9800
C5A—C6A	1.532 (15)	C5B—C6B	1.529 (15)
C6A—C1A	1.534 (16)	C11B—H11B	0.9800
C6A—C7A	1.532 (16)	C11B—C12B	1.517 (15)
C1A—H1A	0.9800	C11B—C13B	1.525 (16)
C1A—C2A	1.528 (16)	C11B—C7B	1.541 (16)
C1A—C10A	1.537 (15)	C6B—C1B	1.529 (16)
C2A—H2AA	0.9700	C6B—C7B	1.533 (16)
C2A—H2AB	0.9700	C1B—H1B	0.9800
C2A—C3A	1.535 (15)	C1B—C2B	1.524 (16)
C3A—H3AA	0.9700	C1B—C10B	1.544 (15)
C3A—H3AB	0.9700	C2B—H2BA	0.9700
C12A—C11A	1.519 (15)	C2B—H2BB	0.9700
C11A—H11A	0.9800	C2B—C3B	1.530 (15)
C11A—C13A	1.526 (16)	C3B—H3BA	0.9700
C11A—C7A	1.542 (16)	C3B—H3BB	0.9700
C13A—H13A	0.9600	C13B—H13D	0.9600
C13A—H13B	0.9600	C13B—H13E	0.9600
C13A—H13C	0.9600	C13B—H13F	0.9600
C7A—H7A	0.9800	C7B—H7B	0.9800
C7A—C8A	1.535 (15)	C7B—C8B	1.541 (15)
C8A—H8AA	0.9700	C8B—H8BA	0.9700
C8A—H8AB	0.9700	C8B—H8BB	0.9700
C8A—C9A	1.524 (16)	C8B—C9B	1.524 (16)
C9A—H9AA	0.9700	C9B—H9BA	0.9700
C9A—H9AB	0.9700	C9B—H9BB	0.9700
C9A—C10A	1.527 (16)	C9B—C10B	1.526 (16)
C10A—H10A	0.9800	C10B—H10B	0.9800
C10A—C14A	1.529 (16)	C10B—C14B	1.528 (16)
C14A—H14A	0.9600	C14B—H14D	0.9600
C14A—H14B	0.9600	C14B—H14E	0.9600
C14A—H14C	0.9600	C14B—H14F	0.9600

C5A—O3A—C4A	114 (3)	C5B—O3B—C4B	113 (3)
C4A—O1A—O2A	107 (3)	C4B—O1B—O2B	105 (3)
C6A—O2A—O1A	108 (2)	C6B—O2B—O1B	108.2 (19)
C12A—O4A—C5A	123 (3)	C12B—O4B—C5B	119 (4)
H15A—C15A—H15B	109.5	H15D—C15B—H15E	109.5
H15A—C15A—H15C	109.5	H15D—C15B—H15F	109.5
H15B—C15A—H15C	109.5	H15E—C15B—H15F	109.5
C4A—C15A—H15A	109.5	C4B—C15B—H15D	109.5
C4A—C15A—H15B	109.5	C4B—C15B—H15E	109.5
C4A—C15A—H15C	109.5	C4B—C15B—H15F	109.5
O3A—C4A—C15A	104 (3)	O3B—C4B—C15B	105 (3)
O3A—C4A—C3A	109 (3)	O3B—C4B—C3B	107 (3)
O1A—C4A—O3A	109 (3)	O1B—C4B—O3B	107 (3)
O1A—C4A—C15A	102 (4)	O1B—C4B—C15B	98 (4)
O1A—C4A—C3A	116 (3)	O1B—C4B—C3B	116 (3)
C15A—C4A—C3A	116 (4)	C15B—C4B—C3B	122 (4)
O3A—C5A—O4A	105 (3)	O3B—C5B—O4B	105 (4)
O3A—C5A—H5A	110.2	O3B—C5B—H5B	108.5
O3A—C5A—C6A	108 (3)	O3B—C5B—C6B	114 (3)
O4A—C5A—H5A	110.2	O4B—C5B—H5B	108.5
O4A—C5A—C6A	112 (3)	O4B—C5B—C6B	113 (3)
C6A—C5A—H5A	110.2	C6B—C5B—H5B	108.5
O2A—C6A—C5A	115 (2)	C12B—C11B—H11B	108.4
O2A—C6A—C1A	112 (3)	C12B—C11B—C13B	111 (4)
O2A—C6A—C7A	102 (3)	C12B—C11B—C7B	111 (4)
C5A—C6A—C1A	110 (3)	C13B—C11B—H11B	108.4
C5A—C6A—C7A	105 (4)	C13B—C11B—C7B	110 (4)
C7A—C6A—C1A	112 (3)	C7B—C11B—H11B	108.4
C6A—C1A—H1A	108.1	O2B—C6B—C5B	113 (2)
C6A—C1A—C10A	111 (3)	O2B—C6B—C1B	102 (3)
C2A—C1A—C6A	112 (3)	O2B—C6B—C7B	106 (3)
C2A—C1A—H1A	108.1	C5B—C6B—C7B	113 (4)
C2A—C1A—C10A	109 (4)	C1B—C6B—C5B	109 (4)
C10A—C1A—H1A	108.1	C1B—C6B—C7B	113 (3)
C1A—C2A—H2AA	108.4	C6B—C1B—H1B	107.7
C1A—C2A—H2AB	108.4	C6B—C1B—C10B	109 (3)
C1A—C2A—C3A	116 (4)	C2B—C1B—C6B	114 (3)
H2AA—C2A—H2AB	107.5	C2B—C1B—H1B	107.7
C3A—C2A—H2AA	108.4	C2B—C1B—C10B	111 (4)
C3A—C2A—H2AB	108.4	C10B—C1B—H1B	107.7
C4A—C3A—C2A	113 (3)	C1B—C2B—H2BA	107.8
C4A—C3A—H3AA	109.1	C1B—C2B—H2BB	107.8
C4A—C3A—H3AB	109.1	C1B—C2B—C3B	118 (4)
C2A—C3A—H3AA	109.1	H2BA—C2B—H2BB	107.1
C2A—C3A—H3AB	109.1	C3B—C2B—H2BA	107.8
H3AA—C3A—H3AB	107.8	C3B—C2B—H2BB	107.8
O4A—C12A—C11A	115 (4)	C4B—C3B—H3BA	108.7
O5A—C12A—O4A	121 (3)	C4B—C3B—H3BB	108.7
O5A—C12A—C11A	123 (4)	C2B—C3B—C4B	114 (4)
C12A—C11A—H11A	108.0	C2B—C3B—H3BA	108.7
C12A—C11A—C13A	108 (4)	C2B—C3B—H3BB	108.7
C12A—C11A—C7A	111 (4)	H3BA—C3B—H3BB	107.6
C13A—C11A—H11A	108.0	O4B—C12B—C11B	118 (5)
C13A—C11A—C7A	114 (4)	O5B—C12B—O4B	123 (4)
C7A—C11A—H11A	108.0	O5B—C12B—C11B	118 (4)
C11A—C13A—H13A	109.5	C11B—C13B—H13D	109.5
C11A—C13A—H13B	109.5	C11B—C13B—H13E	109.5
C11A—C13A—H13C	109.5	C11B—C13B—H13F	109.5
H13A—C13A—H13B	109.5	H13D—C13B—H13E	109.5
H13A—C13A—H13C	109.5	H13D—C13B—H13F	109.5
H13B—C13A—H13C	109.5	H13E—C13B—H13F	109.5
C6A—C7A—C11A	111 (3)	C11B—C7B—H7B	109.0
C6A—C7A—H7A	106.3	C11B—C7B—C8B	115 (3)
C6A—C7A—C8A	114 (4)	C6B—C7B—C11B	104 (3)
C11A—C7A—H7A	106.3	C6B—C7B—H7B	109.0
C8A—C7A—C11A	112 (4)	C6B—C7B—C8B	110 (3)
C8A—C7A—H7A	106.3	C8B—C7B—H7B	109.0
C7A—C8A—H8AA	109.6	C7B—C8B—H8BA	110.4
C7A—C8A—H8AB	109.6	C7B—C8B—H8BB	110.4
H8AA—C8A—H8AB	108.1	H8BA—C8B—H8BB	108.6
C9A—C8A—C7A	110 (4)	C9B—C8B—C7B	106 (4)
C9A—C8A—H8AA	109.6	C9B—C8B—H8BA	110.4
C9A—C8A—H8AB	109.6	C9B—C8B—H8BB	110.4
C8A—C9A—H9AA	108.3	C8B—C9B—H9BA	108.8
C8A—C9A—H9AB	108.3	C8B—C9B—H9BB	108.8
C8A—C9A—C10A	116 (4)	C8B—C9B—C10B	114 (4)
H9AA—C9A—H9AB	107.4	H9BA—C9B—H9BB	107.7
C10A—C9A—H9AA	108.3	C10B—C9B—H9BA	108.8
C10A—C9A—H9AB	108.3	C10B—C9B—H9BB	108.8
C1A—C10A—H10A	105.8	C1B—C10B—H10B	108.4
C9A—C10A—C1A	112 (4)	C9B—C10B—C1B	110 (4)
C9A—C10A—H10A	105.8	C9B—C10B—H10B	108.4
C9A—C10A—C14A	112 (4)	C9B—C10B—C14B	110 (4)
C14A—C10A—C1A	115 (4)	C14B—C10B—C1B	112 (4)
C14A—C10A—H10A	105.8	C14B—C10B—H10B	108.4
C10A—C14A—H14A	109.5	C10B—C14B—H14D	109.5
C10A—C14A—H14B	109.5	C10B—C14B—H14E	109.5
C10A—C14A—H14C	109.5	C10B—C14B—H14F	109.5
H14A—C14A—H14B	109.5	H14D—C14B—H14E	109.5
H14A—C14A—H14C	109.5	H14D—C14B—H14F	109.5
H14B—C14A—H14C	109.5	H14E—C14B—H14F	109.5

O3A—C4A—C3A—C2A	26 (5)	O3B—C4B—C3B—C2B	30 (5)
O3A—C5A—C6A—O2A	−58 (6)	O3B—C5B—C6B—O2B	−47 (6)
O3A—C5A—C6A—C1A	69 (3)	O3B—C5B—C6B—C1B	66 (4)
O3A—C5A—C6A—C7A	−170 (3)	O3B—C5B—C6B—C7B	−167 (3)
O1A—O2A—C6A—C5A	19 (6)	O1B—O2B—C6B—C5B	2 (6)
O1A—O2A—C6A—C1A	−107 (4)	O1B—O2B—C6B—C1B	−115 (4)
O1A—O2A—C6A—C7A	132 (3)	O1B—O2B—C6B—C7B	127 (4)
O1A—C4A—C3A—C2A	−97 (4)	O1B—C4B—C3B—C2B	−89 (4)
O2A—O1A—C4A—O3A	−77 (3)	O2B—O1B—C4B—O3B	−80 (3)
O2A—O1A—C4A—C15A	174 (3)	O2B—O1B—C4B—C15B	171 (3)
O2A—O1A—C4A—C3A	47 (3)	O2B—O1B—C4B—C3B	40 (3)
O2A—C6A—C1A—C2A	70 (4)	O2B—C6B—C1B—C2B	68 (4)
O2A—C6A—C1A—C10A	−168 (4)	O2B—C6B—C1B—C10B	−168 (3)
O2A—C6A—C7A—C11A	−58 (4)	O2B—C6B—C7B—C11B	−66 (3)
O2A—C6A—C7A—C8A	174 (3)	O2B—C6B—C7B—C8B	170 (3)
O4A—C5A—C6A—O2A	58 (6)	O4B—C5B—C6B—O2B	72 (5)
O4A—C5A—C6A—C1A	−175 (3)	O4B—C5B—C6B—C1B	−175 (3)
O4A—C5A—C6A—C7A	−54 (3)	O4B—C5B—C6B—C7B	−48 (4)
O4A—C12A—C11A—C13A	165 (4)	C15B—C4B—C3B—C2B	152 (4)
O4A—C12A—C11A—C7A	39 (5)	C4B—O3B—C5B—O4B	−96 (3)
O5A—C12A—C11A—C13A	−16 (6)	C4B—O3B—C5B—C6B	28 (5)
O5A—C12A—C11A—C7A	−141 (4)	C4B—O1B—O2B—C6B	58 (4)
C15A—C4A—C3A—C2A	143 (4)	C5B—O3B—C4B—O1B	32 (4)
C4A—O3A—C5A—O4A	−93 (3)	C5B—O3B—C4B—C15B	136 (5)
C4A—O3A—C5A—C6A	28 (4)	C5B—O3B—C4B—C3B	−92 (4)
C4A—O1A—O2A—C6A	45 (4)	C5B—O4B—C12B—O5B	152 (4)
C5A—O3A—C4A—O1A	35 (3)	C5B—O4B—C12B—C11B	−38 (6)
C5A—O3A—C4A—C15A	143 (4)	C5B—C6B—C1B—C2B	−52 (4)
C5A—O3A—C4A—C3A	−93 (3)	C5B—C6B—C1B—C10B	72 (4)
C5A—O4A—C12A—O5A	145 (3)	C5B—C6B—C7B—C11B	58 (3)
C5A—O4A—C12A—C11A	−36 (5)	C5B—C6B—C7B—C8B	−66 (4)
C5A—C6A—C1A—C2A	−59 (4)	C11B—C7B—C8B—C9B	−176 (3)
C5A—C6A—C1A—C10A	63 (4)	C6B—C1B—C2B—C3B	−34 (5)
C5A—C6A—C7A—C11A	62 (3)	C6B—C1B—C10B—C9B	53 (4)
C5A—C6A—C7A—C8A	−66 (4)	C6B—C1B—C10B—C14B	176 (3)
C6A—C1A—C2A—C3A	−33 (4)	C6B—C7B—C8B—C9B	−58 (4)
C6A—C1A—C10A—C9A	52 (4)	C1B—C6B—C7B—C11B	−176 (2)
C6A—C1A—C10A—C14A	−179 (3)	C1B—C6B—C7B—C8B	59 (3)
C6A—C7A—C8A—C9A	−49 (4)	C1B—C2B—C3B—C4B	52 (5)
C1A—C6A—C7A—C11A	−179 (2)	C2B—C1B—C10B—C9B	179 (3)
C1A—C6A—C7A—C8A	53 (4)	C2B—C1B—C10B—C14B	−58 (5)
C1A—C2A—C3A—C4A	55 (4)	C12B—O4B—C5B—O3B	160 (3)
C2A—C1A—C10A—C9A	176 (3)	C12B—O4B—C5B—C6B	36 (5)
C2A—C1A—C10A—C14A	−55 (4)	C12B—C11B—C7B—C6B	−57 (4)
C12A—O4A—C5A—O3A	162 (3)	C12B—C11B—C7B—C8B	63 (5)
C12A—O4A—C5A—C6A	44 (5)	C13B—C11B—C12B—O4B	173 (4)
C12A—C11A—C7A—C6A	−55 (5)	C13B—C11B—C12B—O5B	−17 (5)
C12A—C11A—C7A—C8A	74 (5)	C13B—C11B—C7B—C6B	180 (3)
C11A—C7A—C8A—C9A	−176 (3)	C13B—C11B—C7B—C8B	−59 (4)
C13A—C11A—C7A—C6A	−177 (3)	C7B—C11B—C12B—O4B	50 (5)
C13A—C11A—C7A—C8A	−48 (5)	C7B—C11B—C12B—O5B	−140 (4)
C7A—C6A—C1A—C2A	−176 (3)	C7B—C6B—C1B—C2B	−180 (3)
C7A—C6A—C1A—C10A	−53 (4)	C7B—C6B—C1B—C10B	−56 (4)
C7A—C8A—C9A—C10A	48 (5)	C7B—C8B—C9B—C10B	60 (5)
C8A—C9A—C10A—C1A	−51 (5)	C8B—C9B—C10B—C1B	−59 (5)
C8A—C9A—C10A—C14A	178 (3)	C8B—C9B—C10B—C14B	178 (3)
C10A—C1A—C2A—C3A	−157 (3)	C10B—C1B—C2B—C3B	−157 (4)

Artemisinin (FormIII_5) top

Crystal data top

C₁₅H₂₂O₅	F(000) = 608
M_r = 282.32	D_x = 1.667 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 9.0393 (13) Å	Cell parameters from 785 reflections
b = 13.688 (2) Å	θ = 2.8–19.1°
c = 9.404 (4) Å	µ = 0.12 mm⁻¹
β = 104.79 (3)°	T = 296 K
V = 1125.0 (5) Å³	Prism, clear colourless
Z = 4	0.2 × 0.1 × 0.09 mm

Data collection top

Bruker D8 Venture diffractometer	1239 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	621 reflections with I > 2σ(I)
Mirror optics monochromator	R_int = 0.133
ω scans	θ_max = 23.4°, θ_min = 2.3°
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1061 before and 0.0702 after correction. The Ratio of minimum to maximum transmission is 0.7780. The λ/2 correction factor is Not present.	h = −10→10
T_min = 0.580, T_max = 0.745	k = −15→15
5919 measured reflections	l = −4→4

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.064	w = 1/[σ²(F_o²) + (0.0533P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.140	(Δ/σ)_max < 0.001
S = 0.98	Δρ_max = 0.18 e Å⁻³
1239 reflections	Δρ_min = −0.18 e Å⁻³
167 parameters	Absolute structure: Flack x determined using 213 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
47 restraints	Absolute structure parameter: 0.9 (10)

Special details top

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

	x	y	z	U_iso*/U_eq
O3A	0.7938 (12)	0.3120 (8)	0.718 (3)	0.029 (4)*
O1A	1.0218 (13)	0.2285 (8)	0.802 (3)	0.031 (4)*
O2A	1.1138 (11)	0.3144 (7)	0.861 (3)	0.026 (3)*
O4A	0.8321 (13)	0.3098 (9)	0.970 (3)	0.033 (4)*
O5A	0.8474 (13)	0.3106 (8)	1.209 (3)	0.036 (4)*
C15A	0.832 (2)	0.1605 (12)	0.612 (5)	0.040 (6)*
H15A	0.792112	0.128652	0.685686	0.061*
H15B	0.905682	0.118752	0.585335	0.061*
H15C	0.749912	0.173886	0.527289	0.061*
C4A	0.9080 (18)	0.2552 (10)	0.674 (3)	0.027 (6)*
C5A	0.8492 (16)	0.3669 (13)	0.846 (3)	0.027 (6)*
H5A	0.786614	0.425934	0.839482	0.032*
C6A	1.0164 (16)	0.3977 (10)	0.865 (3)	0.025 (6)*
C1A	1.026 (2)	0.4676 (11)	0.740 (4)	0.032 (6)*
H1A	1.134714	0.482175	0.751463	0.038*
C2A	0.964 (2)	0.4258 (11)	0.586 (4)	0.038 (7)*
H2AA	1.017453	0.457107	0.521283	0.045*
H2AB	0.856856	0.444744	0.552271	0.045*
C3A	0.9731 (19)	0.3145 (11)	0.566 (3)	0.028 (5)*
H3AA	0.917826	0.297552	0.466151	0.033*
H3AB	1.079391	0.296346	0.577934	0.033*
C12A	0.9058 (19)	0.3304 (14)	1.110 (3)	0.033 (8)*
C11A	1.0696 (19)	0.3686 (15)	1.138 (3)	0.035 (7)*
H11A	1.137254	0.313259	1.134752	0.042*
C13A	1.116 (2)	0.4126 (15)	1.293 (4)	0.040 (7)*
H13A	1.041056	0.459732	1.303205	0.060*
H13B	1.213860	0.443926	1.307287	0.060*
H13C	1.122682	0.361711	1.364208	0.060*
C7A	1.080 (2)	0.4409 (10)	1.017 (3)	0.021 (5)*
H7A	1.189137	0.453577	1.027794	0.025*
C8A	1.006 (2)	0.5392 (10)	1.036 (4)	0.030 (6)*
H8AA	0.901187	0.528059	1.041418	0.036*
H8AB	1.060921	0.568985	1.127953	0.036*
C9A	1.005 (2)	0.6090 (14)	0.910 (4)	0.039 (7)*
H9AA	0.942742	0.665273	0.918093	0.047*
H9AB	1.108772	0.632080	0.919496	0.047*
C10A	0.946 (2)	0.5652 (11)	0.756 (4)	0.034 (6)*
H10A	0.837603	0.549584	0.745926	0.041*
C14A	0.950 (2)	0.6361 (13)	0.633 (4)	0.036 (7)*
H14A	1.054829	0.647355	0.631234	0.054*
H14B	0.903997	0.696781	0.648661	0.054*
H14C	0.895443	0.608663	0.540378	0.054*
O3B	0.3091 (14)	0.0040 (9)	0.713 (3)	0.032 (4)*
O1B	0.5602 (15)	−0.0423 (8)	0.799 (3)	0.039 (4)*
O2B	0.6224 (12)	0.0564 (7)	0.837 (3)	0.026 (4)*
O4B	0.3493 (15)	0.0119 (9)	0.964 (3)	0.030 (4)*
O5B	0.3897 (15)	0.0164 (10)	1.211 (4)	0.043 (5)*
C15B	0.4037 (18)	−0.1361 (11)	0.631 (5)	0.032 (6)*
H15D	0.346768	−0.162931	0.695132	0.049*
H15E	0.497407	−0.171796	0.642528	0.049*
H15F	0.344165	−0.140788	0.530957	0.049*
C4B	0.4393 (19)	−0.0311 (10)	0.669 (3)	0.027 (6)*
C5B	0.3467 (17)	0.0679 (14)	0.833 (3)	0.032 (6)*
H5B	0.265079	0.116735	0.820368	0.039*
C11B	0.576 (2)	0.0940 (12)	1.115 (3)	0.025 (6)*
H11B	0.650773	0.046528	1.098028	0.030*
C6B	0.4974 (16)	0.1217 (10)	0.846 (3)	0.018 (5)*
C1B	0.481 (2)	0.1915 (10)	0.717 (3)	0.021 (5)*
H1B	0.583348	0.216590	0.721319	0.026*
C2B	0.424 (2)	0.1433 (11)	0.567 (4)	0.040 (7)*
H2BA	0.459229	0.182406	0.495693	0.048*
H2BB	0.313428	0.145651	0.539678	0.048*
C3B	0.473 (2)	0.0374 (10)	0.552 (4)	0.043 (7)*
H3BA	0.581919	0.035983	0.559175	0.051*
H3BB	0.420235	0.013250	0.455642	0.051*
C12B	0.428 (2)	0.0382 (14)	1.100 (4)	0.044 (9)*
C13B	0.636 (2)	0.1282 (13)	1.273 (4)	0.030 (6)*
H13D	0.553509	0.156912	1.306558	0.046*
H13E	0.714813	0.175899	1.278671	0.046*
H13F	0.676410	0.073502	1.334828	0.046*
C7B	0.5571 (17)	0.1707 (10)	0.994 (3)	0.011 (5)*
H7B	0.657877	0.198584	0.997535	0.014*
C8B	0.450 (2)	0.2543 (11)	1.014 (4)	0.033 (6)*
H8BA	0.349312	0.228852	1.012627	0.039*
H8BB	0.490779	0.286754	1.107885	0.039*
C9B	0.4397 (19)	0.3256 (12)	0.888 (3)	0.030 (6)*
H9BA	0.371666	0.378588	0.897624	0.036*
H9BB	0.540242	0.353367	0.896232	0.036*
C10B	0.383 (2)	0.2803 (11)	0.736 (3)	0.029 (6)*
H10B	0.278349	0.256777	0.727814	0.035*
C14B	0.3748 (19)	0.3557 (15)	0.616 (4)	0.044 (7)*
H14D	0.475785	0.379756	0.621028	0.066*
H14E	0.310455	0.408930	0.629217	0.066*
H14F	0.333270	0.326025	0.521778	0.066*

Geometric parameters (Å, º) top

O3A—C4A	1.438 (13)	O3B—C4B	1.426 (13)
O3A—C5A	1.395 (14)	O3B—C5B	1.397 (14)
O1A—O2A	1.467 (12)	O1B—O2B	1.472 (11)
O1A—C4A	1.417 (14)	O1B—C4B	1.421 (15)
O2A—C6A	1.446 (12)	O2B—C6B	1.458 (12)
O4A—C5A	1.446 (14)	O4B—C5B	1.448 (14)
O4A—C12A	1.347 (14)	O4B—C12B	1.345 (14)
O5A—C12A	1.209 (14)	O5B—C12B	1.209 (15)
C15A—H15A	0.9600	C15B—H15D	0.9600
C15A—H15B	0.9600	C15B—H15E	0.9600
C15A—H15C	0.9600	C15B—H15F	0.9600
C15A—C4A	1.511 (14)	C15B—C4B	1.496 (13)
C4A—C3A	1.530 (15)	C4B—C3B	1.536 (15)
C5A—H5A	0.9800	C5B—H5B	0.9800
C5A—C6A	1.536 (13)	C5B—C6B	1.526 (13)
C6A—C1A	1.530 (14)	C11B—H11B	0.9800
C6A—C7A	1.524 (15)	C11B—C12B	1.520 (14)
C1A—H1A	0.9800	C11B—C13B	1.519 (15)
C1A—C2A	1.528 (15)	C11B—C7B	1.530 (15)
C1A—C10A	1.548 (13)	C6B—C1B	1.520 (14)
C2A—H2AA	0.9700	C6B—C7B	1.517 (15)
C2A—H2AB	0.9700	C1B—H1B	0.9800
C2A—C3A	1.542 (13)	C1B—C2B	1.520 (15)
C3A—H3AA	0.9700	C1B—C10B	1.544 (13)
C3A—H3AB	0.9700	C2B—H2BA	0.9700
C12A—C11A	1.528 (14)	C2B—H2BB	0.9700
C11A—H11A	0.9800	C2B—C3B	1.531 (13)
C11A—C13A	1.526 (15)	C3B—H3BA	0.9700
C11A—C7A	1.530 (15)	C3B—H3BB	0.9700
C13A—H13A	0.9600	C13B—H13D	0.9600
C13A—H13B	0.9600	C13B—H13E	0.9600
C13A—H13C	0.9600	C13B—H13F	0.9600
C7A—H7A	0.9800	C7B—H7B	0.9800
C7A—C8A	1.536 (13)	C7B—C8B	1.543 (13)
C8A—H8AA	0.9700	C8B—H8BA	0.9700
C8A—H8AB	0.9700	C8B—H8BB	0.9700
C8A—C9A	1.526 (15)	C8B—C9B	1.522 (15)
C9A—H9AA	0.9700	C9B—H9BA	0.9700
C9A—H9AB	0.9700	C9B—H9BB	0.9700
C9A—C10A	1.525 (15)	C9B—C10B	1.519 (15)
C10A—H10A	0.9800	C10B—H10B	0.9800
C10A—C14A	1.524 (15)	C10B—C14B	1.520 (15)
C14A—H14A	0.9600	C14B—H14D	0.9600
C14A—H14B	0.9600	C14B—H14E	0.9600
C14A—H14C	0.9600	C14B—H14F	0.9600

C5A—O3A—C4A	114.6 (13)	C5B—O3B—C4B	113.2 (15)
C4A—O1A—O2A	109.7 (13)	C4B—O1B—O2B	105.9 (14)
C6A—O2A—O1A	110.6 (10)	C6B—O2B—O1B	108.9 (10)
C12A—O4A—C5A	123.3 (14)	C12B—O4B—C5B	124.1 (15)
H15A—C15A—H15B	109.5	H15D—C15B—H15E	109.5
H15A—C15A—H15C	109.5	H15D—C15B—H15F	109.5
H15B—C15A—H15C	109.5	H15E—C15B—H15F	109.5
C4A—C15A—H15A	109.5	C4B—C15B—H15D	109.5
C4A—C15A—H15B	109.5	C4B—C15B—H15E	109.5
C4A—C15A—H15C	109.5	C4B—C15B—H15F	109.5
O3A—C4A—C15A	106.6 (14)	O3B—C4B—C15B	104.5 (14)
O3A—C4A—C3A	109.6 (15)	O3B—C4B—C3B	109.4 (15)
O1A—C4A—O3A	108.1 (15)	O1B—C4B—O3B	107.5 (16)
O1A—C4A—C15A	105.2 (18)	O1B—C4B—C15B	100.0 (19)
O1A—C4A—C3A	112.4 (15)	O1B—C4B—C3B	115.4 (15)
C15A—C4A—C3A	114.6 (18)	C15B—C4B—C3B	119 (2)
O3A—C5A—O4A	108.3 (15)	O3B—C5B—O4B	107.6 (17)
O3A—C5A—H5A	108.4	O3B—C5B—H5B	108.1
O3A—C5A—C6A	111.9 (17)	O3B—C5B—C6B	113.2 (17)
O4A—C5A—H5A	108.4	O4B—C5B—H5B	108.1
O4A—C5A—C6A	111.2 (16)	O4B—C5B—C6B	111.6 (17)
C6A—C5A—H5A	108.4	C6B—C5B—H5B	108.1
O2A—C6A—C5A	111.6 (12)	C12B—C11B—H11B	106.3
O2A—C6A—C1A	108.9 (17)	C12B—C11B—C7B	110.3 (17)
O2A—C6A—C7A	103.8 (17)	C13B—C11B—H11B	106.3
C1A—C6A—C5A	109.4 (16)	C13B—C11B—C12B	109.3 (19)
C7A—C6A—C5A	109.8 (19)	C13B—C11B—C7B	117.6 (17)
C7A—C6A—C1A	113.3 (15)	C7B—C11B—H11B	106.3
C6A—C1A—H1A	107.2	O2B—C6B—C5B	112.8 (13)
C6A—C1A—C10A	110.1 (17)	O2B—C6B—C1B	105.3 (16)
C2A—C1A—C6A	114.3 (17)	O2B—C6B—C7B	102.8 (16)
C2A—C1A—H1A	107.2	C1B—C6B—C5B	109.6 (17)
C2A—C1A—C10A	110.3 (19)	C7B—C6B—C5B	112.7 (19)
C10A—C1A—H1A	107.2	C7B—C6B—C1B	113.3 (14)
C1A—C2A—H2AA	107.8	C6B—C1B—H1B	106.5
C1A—C2A—H2AB	107.8	C6B—C1B—C10B	110.0 (16)
C1A—C2A—C3A	118 (2)	C2B—C1B—C6B	114.1 (15)
H2AA—C2A—H2AB	107.2	C2B—C1B—H1B	106.5
C3A—C2A—H2AA	107.8	C2B—C1B—C10B	112.8 (18)
C3A—C2A—H2AB	107.8	C10B—C1B—H1B	106.5
C4A—C3A—C2A	113.5 (18)	C1B—C2B—H2BA	108.0
C4A—C3A—H3AA	108.9	C1B—C2B—H2BB	108.0
C4A—C3A—H3AB	108.9	C1B—C2B—C3B	117 (2)
C2A—C3A—H3AA	108.9	H2BA—C2B—H2BB	107.2
C2A—C3A—H3AB	108.9	C3B—C2B—H2BA	108.0
H3AA—C3A—H3AB	107.7	C3B—C2B—H2BB	108.0
O4A—C12A—C11A	117 (2)	C4B—C3B—H3BA	108.9
O5A—C12A—O4A	120.0 (17)	C4B—C3B—H3BB	108.9
O5A—C12A—C11A	123 (2)	C2B—C3B—C4B	113.5 (19)
C12A—C11A—H11A	108.4	C2B—C3B—H3BA	108.9
C12A—C11A—C7A	109.6 (17)	C2B—C3B—H3BB	108.9
C13A—C11A—C12A	108.6 (19)	H3BA—C3B—H3BB	107.7
C13A—C11A—H11A	108.4	O4B—C12B—C11B	117 (2)
C13A—C11A—C7A	113.5 (17)	O5B—C12B—O4B	123.8 (19)
C7A—C11A—H11A	108.4	O5B—C12B—C11B	119 (2)
C11A—C13A—H13A	109.5	C11B—C13B—H13D	109.5
C11A—C13A—H13B	109.5	C11B—C13B—H13E	109.5
C11A—C13A—H13C	109.5	C11B—C13B—H13F	109.5
H13A—C13A—H13B	109.5	H13D—C13B—H13E	109.5
H13A—C13A—H13C	109.5	H13D—C13B—H13F	109.5
H13B—C13A—H13C	109.5	H13E—C13B—H13F	109.5
C6A—C7A—C11A	111.8 (15)	C11B—C7B—H7B	108.3
C6A—C7A—H7A	107.0	C11B—C7B—C8B	111.7 (17)
C6A—C7A—C8A	112.2 (19)	C6B—C7B—C11B	109.3 (15)
C11A—C7A—H7A	107.0	C6B—C7B—H7B	108.3
C11A—C7A—C8A	111.6 (18)	C6B—C7B—C8B	110.9 (17)
C8A—C7A—H7A	107.0	C8B—C7B—H7B	108.3
C7A—C8A—H8AA	109.2	C7B—C8B—H8BA	110.3
C7A—C8A—H8AB	109.2	C7B—C8B—H8BB	110.3
H8AA—C8A—H8AB	107.9	H8BA—C8B—H8BB	108.6
C9A—C8A—C7A	111.9 (19)	C9B—C8B—C7B	107.0 (17)
C9A—C8A—H8AA	109.2	C9B—C8B—H8BA	110.3
C9A—C8A—H8AB	109.2	C9B—C8B—H8BB	110.3
C8A—C9A—H9AA	108.6	C8B—C9B—H9BA	108.7
C8A—C9A—H9AB	108.6	C8B—C9B—H9BB	108.7
H9AA—C9A—H9AB	107.5	H9BA—C9B—H9BB	107.6
C10A—C9A—C8A	114.9 (18)	C10B—C9B—C8B	114.2 (16)
C10A—C9A—H9AA	108.6	C10B—C9B—H9BA	108.7
C10A—C9A—H9AB	108.6	C10B—C9B—H9BB	108.7
C1A—C10A—H10A	106.5	C1B—C10B—H10B	107.5
C9A—C10A—C1A	112 (2)	C9B—C10B—C1B	111.5 (18)
C9A—C10A—H10A	106.5	C9B—C10B—H10B	107.5
C14A—C10A—C1A	111.6 (18)	C9B—C10B—C14B	111.3 (17)
C14A—C10A—C9A	113.5 (18)	C14B—C10B—C1B	111.3 (18)
C14A—C10A—H10A	106.5	C14B—C10B—H10B	107.5
C10A—C14A—H14A	109.5	C10B—C14B—H14D	109.5
C10A—C14A—H14B	109.5	C10B—C14B—H14E	109.5
C10A—C14A—H14C	109.5	C10B—C14B—H14F	109.5
H14A—C14A—H14B	109.5	H14D—C14B—H14E	109.5
H14A—C14A—H14C	109.5	H14D—C14B—H14F	109.5
H14B—C14A—H14C	109.5	H14E—C14B—H14F	109.5

O3A—C4A—C3A—C2A	27 (2)	O3B—C4B—C3B—C2B	29 (2)
O3A—C5A—C6A—O2A	−55 (3)	O3B—C5B—C6B—O2B	−50 (3)
O3A—C5A—C6A—C1A	65.3 (19)	O3B—C5B—C6B—C1B	67 (2)
O3A—C5A—C6A—C7A	−169.8 (14)	O3B—C5B—C6B—C7B	−165.6 (14)
O1A—O2A—C6A—C5A	16 (3)	O1B—O2B—C6B—C5B	8 (3)
O1A—O2A—C6A—C1A	−105.1 (18)	O1B—O2B—C6B—C1B	−111.9 (19)
O1A—O2A—C6A—C7A	133.8 (17)	O1B—O2B—C6B—C7B	129.3 (18)
O1A—C4A—C3A—C2A	−93.4 (19)	O1B—C4B—C3B—C2B	−92 (2)
O2A—O1A—C4A—O3A	−72.3 (16)	O2B—O1B—C4B—O3B	−79.3 (15)
O2A—O1A—C4A—C15A	174.1 (14)	O2B—O1B—C4B—C15B	171.9 (17)
O2A—O1A—C4A—C3A	48.7 (16)	O2B—O1B—C4B—C3B	43.1 (18)
O2A—C6A—C1A—C2A	64.8 (19)	O2B—C6B—C1B—C2B	67.2 (19)
O2A—C6A—C1A—C10A	−170.4 (19)	O2B—C6B—C1B—C10B	−165.0 (16)
O2A—C6A—C7A—C11A	−61.5 (18)	O2B—C6B—C7B—C11B	−64.6 (14)
O2A—C6A—C7A—C8A	172.3 (14)	O2B—C6B—C7B—C8B	171.9 (14)
O4A—C5A—C6A—O2A	66 (3)	O4B—C5B—C6B—O2B	72 (3)
O4A—C5A—C6A—C1A	−173.4 (14)	O4B—C5B—C6B—C1B	−171.2 (14)
O4A—C5A—C6A—C7A	−48.5 (17)	O4B—C5B—C6B—C7B	−44 (2)
O4A—C12A—C11A—C13A	165.0 (17)	C15B—C4B—C3B—C2B	149 (2)
O4A—C12A—C11A—C7A	41 (2)	C4B—O3B—C5B—O4B	−97.5 (16)
O5A—C12A—C11A—C13A	−22 (3)	C4B—O3B—C5B—C6B	26 (2)
O5A—C12A—C11A—C7A	−146.0 (19)	C4B—O1B—O2B—C6B	53 (2)
C15A—C4A—C3A—C2A	146.5 (19)	C5B—O3B—C4B—O1B	35.2 (19)
C4A—O3A—C5A—O4A	−93.1 (16)	C5B—O3B—C4B—C15B	141 (2)
C4A—O3A—C5A—C6A	30 (2)	C5B—O3B—C4B—C3B	−91 (2)
C4A—O1A—O2A—C6A	45 (2)	C5B—O4B—C12B—O5B	151.3 (18)
C5A—O3A—C4A—O1A	30.7 (17)	C5B—O4B—C12B—C11B	−32 (3)
C5A—O3A—C4A—C15A	143 (2)	C5B—C6B—C1B—C2B	−54 (2)
C5A—O3A—C4A—C3A	−92.1 (19)	C5B—C6B—C1B—C10B	73.4 (19)
C5A—O4A—C12A—O5A	149.5 (16)	C5B—C6B—C7B—C11B	57.2 (17)
C5A—O4A—C12A—C11A	−37 (3)	C5B—C6B—C7B—C8B	−66.3 (18)
C5A—C6A—C1A—C2A	−57 (2)	C11B—C7B—C8B—C9B	180.0 (15)
C5A—C6A—C1A—C10A	67 (2)	C6B—C1B—C2B—C3B	−33 (2)
C5A—C6A—C7A—C11A	57.8 (18)	C6B—C1B—C10B—C9B	50 (2)
C5A—C6A—C7A—C8A	−68.3 (17)	C6B—C1B—C10B—C14B	175.2 (15)
C6A—C1A—C2A—C3A	−29 (2)	C6B—C7B—C8B—C9B	−57.9 (18)
C6A—C1A—C10A—C9A	53 (2)	C1B—C6B—C7B—C11B	−177.7 (12)
C6A—C1A—C10A—C14A	−178.9 (17)	C1B—C6B—C7B—C8B	58.8 (16)
C6A—C7A—C8A—C9A	−49 (2)	C1B—C2B—C3B—C4B	52 (2)
C1A—C6A—C7A—C11A	−179.5 (12)	C2B—C1B—C10B—C9B	178.8 (16)
C1A—C6A—C7A—C8A	54.3 (19)	C2B—C1B—C10B—C14B	−56 (2)
C1A—C2A—C3A—C4A	51 (2)	C12B—O4B—C5B—O3B	156.9 (16)
C2A—C1A—C10A—C9A	179.9 (17)	C12B—O4B—C5B—C6B	32 (3)
C2A—C1A—C10A—C14A	−52 (2)	C12B—C11B—C7B—C6B	−54.0 (19)
C12A—O4A—C5A—O3A	163.6 (14)	C12B—C11B—C7B—C8B	69 (2)
C12A—O4A—C5A—C6A	40 (2)	C13B—C11B—C12B—O4B	172.7 (16)
C12A—C11A—C7A—C6A	−52 (2)	C13B—C11B—C12B—O5B	−11 (3)
C12A—C11A—C7A—C8A	74 (2)	C13B—C11B—C7B—C6B	179.8 (15)
C11A—C7A—C8A—C9A	−175.8 (16)	C13B—C11B—C7B—C8B	−57 (2)
C13A—C11A—C7A—C6A	−173.8 (14)	C7B—C11B—C12B—O4B	42 (2)
C13A—C11A—C7A—C8A	−47 (2)	C7B—C11B—C12B—O5B	−141.3 (19)
C7A—C6A—C1A—C2A	179.8 (14)	C7B—C6B—C1B—C2B	178.7 (13)
C7A—C6A—C1A—C10A	−55 (2)	C7B—C6B—C1B—C10B	−53 (2)
C7A—C8A—C9A—C10A	49 (2)	C7B—C8B—C9B—C10B	58 (2)
C8A—C9A—C10A—C1A	−51 (2)	C8B—C9B—C10B—C1B	−55 (2)
C8A—C9A—C10A—C14A	−178.6 (13)	C8B—C9B—C10B—C14B	179.8 (14)
C10A—C1A—C2A—C3A	−154.2 (16)	C10B—C1B—C2B—C3B	−159.2 (17)

Artemisinin (FormIII_6) top

Crystal data top

C₁₅H₂₂O₅	F(000) = 608
M_r = 282.32	D_x = 1.626 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 9.1279 (16) Å	Cell parameters from 795 reflections
b = 13.819 (3) Å	θ = 2.7–23.2°
c = 9.461 (4) Å	µ = 0.12 mm⁻¹
β = 104.86 (3)°	T = 296 K
V = 1153.5 (6) Å³	Prism, clear colourless
Z = 4	0.2 × 0.1 × 0.09 mm

Data collection top

Bruker D8 Venture diffractometer	1259 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	606 reflections with I > 2σ(I)
Mirror optics monochromator	R_int = 0.137
ω scans	θ_max = 23.3°, θ_min = 2.3°
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0889 before and 0.0633 after correction. The Ratio of minimum to maximum transmission is 0.8829. The λ/2 correction factor is Not present.	h = −10→10
T_min = 0.658, T_max = 0.745	k = −15→15
6247 measured reflections	l = −4→4

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.062	w = 1/[σ²(F_o²) + (0.0495P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.129	(Δ/σ)_max < 0.001
S = 0.99	Δρ_max = 0.18 e Å⁻³
1259 reflections	Δρ_min = −0.20 e Å⁻³
167 parameters	Absolute structure: Flack x determined using 206 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
47 restraints	Absolute structure parameter: 4.4 (10)
Primary atom site location: iterative

Special details top

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

	x	y	z	U_iso*/U_eq
O3A	0.7958 (12)	0.3102 (8)	0.718 (3)	0.034 (4)*
O1A	1.0221 (14)	0.2285 (8)	0.806 (3)	0.033 (4)*
O2A	1.1127 (11)	0.3140 (6)	0.860 (3)	0.027 (3)*
O4A	0.8301 (13)	0.3104 (9)	0.968 (3)	0.035 (4)*
O5A	0.8487 (14)	0.3102 (8)	1.207 (3)	0.039 (4)*
C15A	0.834 (2)	0.1613 (12)	0.614 (4)	0.044 (7)*
H15A	0.806152	0.125134	0.690130	0.066*
H15B	0.902103	0.123725	0.574422	0.066*
H15C	0.744430	0.175990	0.538392	0.066*
C4A	0.9105 (18)	0.2545 (10)	0.677 (3)	0.026 (6)*
C5A	0.8503 (15)	0.3656 (12)	0.845 (3)	0.018 (6)*
H5A	0.788248	0.424291	0.836246	0.022*
C6A	1.0158 (15)	0.3963 (10)	0.863 (3)	0.024 (6)*
C1A	1.024 (2)	0.4656 (11)	0.739 (4)	0.034 (6)*
H1A	1.131062	0.480108	0.749768	0.041*
C2A	0.963 (2)	0.4237 (11)	0.586 (4)	0.045 (7)*
H2AA	1.017269	0.454051	0.521829	0.054*
H2AB	0.857303	0.442835	0.550851	0.054*
C3A	0.971 (2)	0.3126 (11)	0.567 (3)	0.034 (6)*
H3AA	0.914106	0.295354	0.468647	0.041*
H3AB	1.076209	0.294537	0.576254	0.041*
C12A	0.9056 (18)	0.3290 (13)	1.108 (3)	0.029 (8)*
C11A	1.0684 (18)	0.3696 (14)	1.138 (4)	0.035 (7)*
H11A	1.135868	0.314895	1.134453	0.042*
C13A	1.116 (2)	0.4117 (14)	1.293 (4)	0.043 (7)*
H13A	1.037548	0.453646	1.307983	0.065*
H13B	1.208150	0.447808	1.304657	0.065*
H13C	1.131891	0.359968	1.362851	0.065*
C7A	1.0797 (19)	0.4398 (10)	1.014 (3)	0.019 (5)*
H7A	1.187778	0.451821	1.024759	0.022*
C8A	1.007 (2)	0.5375 (10)	1.036 (4)	0.032 (6)*
H8AA	0.904862	0.526922	1.044033	0.038*
H8AB	1.064950	0.567274	1.125844	0.038*
C9A	1.004 (2)	0.6051 (13)	0.908 (4)	0.029 (6)*
H9AA	0.942237	0.660708	0.916292	0.035*
H9AB	1.106449	0.628424	0.916769	0.035*
C10A	0.945 (2)	0.5626 (11)	0.755 (4)	0.035 (6)*
H10A	0.837597	0.547879	0.744000	0.042*
C14A	0.952 (2)	0.6349 (14)	0.636 (4)	0.043 (7)*
H14A	1.055760	0.650326	0.641225	0.065*
H14B	0.898542	0.692732	0.648426	0.065*
H14C	0.905715	0.607065	0.541783	0.065*
O3B	0.3093 (14)	0.0053 (9)	0.717 (3)	0.036 (4)*
O1B	0.5597 (15)	−0.0405 (8)	0.799 (3)	0.043 (4)*
O2B	0.6209 (12)	0.0574 (7)	0.837 (3)	0.031 (4)*
O4B	0.3492 (15)	0.0131 (9)	0.967 (3)	0.035 (5)*
O5B	0.3871 (15)	0.0167 (10)	1.207 (4)	0.046 (5)*
C15B	0.4046 (18)	−0.1335 (11)	0.628 (5)	0.031 (6)*
H15D	0.341588	−0.161316	0.684669	0.046*
H15E	0.497816	−0.169041	0.645191	0.046*
H15F	0.352924	−0.136317	0.526199	0.046*
C4B	0.438 (2)	−0.0299 (11)	0.673 (3)	0.036 (7)*
C5B	0.3493 (17)	0.0687 (13)	0.837 (3)	0.031 (6)*
H5B	0.268611	0.117197	0.824458	0.038*
C11B	0.575 (2)	0.0953 (13)	1.113 (4)	0.031 (6)*
H11B	0.649980	0.049115	1.095719	0.038*
C6B	0.4974 (17)	0.1229 (11)	0.844 (3)	0.029 (6)*
C1B	0.482 (2)	0.1928 (10)	0.717 (3)	0.022 (5)*
H1B	0.584038	0.216792	0.722266	0.026*
C2B	0.426 (2)	0.1453 (10)	0.568 (4)	0.039 (7)*
H2BA	0.463324	0.182515	0.498156	0.047*
H2BB	0.316082	0.149323	0.539783	0.047*
C3B	0.471 (2)	0.0387 (9)	0.558 (4)	0.031 (7)*
H3BA	0.418950	0.014649	0.461616	0.038*
H3BB	0.579100	0.036337	0.564489	0.038*
C12B	0.429 (2)	0.0387 (13)	1.101 (3)	0.040 (8)*
C13B	0.632 (2)	0.1297 (13)	1.270 (4)	0.029 (6)*
H13D	0.551578	0.161778	1.299459	0.043*
H13E	0.714776	0.173952	1.276753	0.043*
H13F	0.666199	0.075149	1.332397	0.043*
C7B	0.5532 (18)	0.1713 (10)	0.992 (3)	0.018 (5)*
H7B	0.652748	0.199570	0.996489	0.022*
C8B	0.448 (2)	0.2541 (11)	1.016 (3)	0.033 (6)*
H8BA	0.348595	0.229322	1.014761	0.039*
H8BB	0.490238	0.285489	1.109653	0.039*
C9B	0.4389 (19)	0.3254 (11)	0.891 (3)	0.030 (6)*
H9BA	0.538150	0.354125	0.901671	0.036*
H9BB	0.369694	0.376954	0.899407	0.036*
C10B	0.3867 (19)	0.2819 (11)	0.737 (3)	0.027 (6)*
H10B	0.283427	0.258162	0.727736	0.032*
C14B	0.3764 (18)	0.3543 (14)	0.613 (4)	0.039 (6)*
H14D	0.476423	0.368593	0.603931	0.058*
H14E	0.329312	0.412748	0.634445	0.058*
H14F	0.317054	0.327036	0.523470	0.058*

Geometric parameters (Å, º) top

O3A—C4A	1.432 (13)	O3B—C4B	1.430 (13)
O3A—C5A	1.399 (14)	O3B—C5B	1.403 (14)
O1A—O2A	1.457 (12)	O1B—O2B	1.472 (11)
O1A—C4A	1.423 (15)	O1B—C4B	1.413 (15)
O2A—C6A	1.446 (12)	O2B—C6B	1.462 (13)
O4A—C5A	1.447 (14)	O4B—C5B	1.449 (14)
O4A—C12A	1.349 (15)	O4B—C12B	1.337 (15)
O5A—C12A	1.212 (14)	O5B—C12B	1.203 (15)
C15A—H15A	0.9600	C15B—H15D	0.9600
C15A—H15B	0.9600	C15B—H15E	0.9600
C15A—H15C	0.9600	C15B—H15F	0.9600
C15A—C4A	1.513 (14)	C15B—C4B	1.502 (13)
C4A—C3A	1.531 (15)	C4B—C3B	1.532 (15)
C5A—H5A	0.9800	C5B—H5B	0.9800
C5A—C6A	1.536 (13)	C5B—C6B	1.531 (13)
C6A—C1A	1.531 (14)	C11B—H11B	0.9800
C6A—C7A	1.526 (15)	C11B—C12B	1.525 (14)
C1A—H1A	0.9800	C11B—C13B	1.518 (15)
C1A—C2A	1.527 (15)	C11B—C7B	1.526 (15)
C1A—C10A	1.548 (13)	C6B—C1B	1.519 (14)
C2A—H2AA	0.9700	C6B—C7B	1.518 (15)
C2A—H2AB	0.9700	C1B—H1B	0.9800
C2A—C3A	1.550 (13)	C1B—C2B	1.518 (15)
C3A—H3AA	0.9700	C1B—C10B	1.547 (13)
C3A—H3AB	0.9700	C2B—H2BA	0.9700
C12A—C11A	1.545 (14)	C2B—H2BB	0.9700
C11A—H11A	0.9800	C2B—C3B	1.541 (13)
C11A—C13A	1.534 (15)	C3B—H3BA	0.9700
C11A—C7A	1.541 (15)	C3B—H3BB	0.9700
C13A—H13A	0.9600	C13B—H13D	0.9600
C13A—H13B	0.9600	C13B—H13E	0.9600
C13A—H13C	0.9600	C13B—H13F	0.9600
C7A—H7A	0.9800	C7B—H7B	0.9800
C7A—C8A	1.539 (13)	C7B—C8B	1.545 (13)
C8A—H8AA	0.9700	C8B—H8BA	0.9700
C8A—H8AB	0.9700	C8B—H8BB	0.9700
C8A—C9A	1.525 (15)	C8B—C9B	1.527 (15)
C9A—H9AA	0.9700	C9B—H9BA	0.9700
C9A—H9AB	0.9700	C9B—H9BB	0.9700
C9A—C10A	1.522 (15)	C9B—C10B	1.529 (15)
C10A—H10A	0.9800	C10B—H10B	0.9800
C10A—C14A	1.523 (15)	C10B—C14B	1.528 (15)
C14A—H14A	0.9600	C14B—H14D	0.9600
C14A—H14B	0.9600	C14B—H14E	0.9600
C14A—H14C	0.9600	C14B—H14F	0.9600

C5A—O3A—C4A	113.7 (13)	C5B—O3B—C4B	112.7 (15)
C4A—O1A—O2A	108.2 (13)	C4B—O1B—O2B	106.2 (14)
C6A—O2A—O1A	110.4 (10)	C6B—O2B—O1B	109.4 (11)
C12A—O4A—C5A	123.5 (14)	C12B—O4B—C5B	123.0 (15)
H15A—C15A—H15B	109.5	H15D—C15B—H15E	109.5
H15A—C15A—H15C	109.5	H15D—C15B—H15F	109.5
H15B—C15A—H15C	109.5	H15E—C15B—H15F	109.5
C4A—C15A—H15A	109.5	C4B—C15B—H15D	109.5
C4A—C15A—H15B	109.5	C4B—C15B—H15E	109.5
C4A—C15A—H15C	109.5	C4B—C15B—H15F	109.5
O3A—C4A—C15A	105.5 (14)	O3B—C4B—C15B	106.5 (15)
O3A—C4A—C3A	108.9 (15)	O3B—C4B—C3B	109.0 (16)
O1A—C4A—O3A	108.3 (15)	O1B—C4B—O3B	108.4 (16)
O1A—C4A—C15A	106.3 (18)	O1B—C4B—C15B	101.4 (18)
O1A—C4A—C3A	114.5 (15)	O1B—C4B—C3B	114.0 (16)
C15A—C4A—C3A	112.9 (18)	C15B—C4B—C3B	116.9 (19)
O3A—C5A—O4A	108.0 (15)	O3B—C5B—O4B	107.2 (17)
O3A—C5A—H5A	108.2	O3B—C5B—H5B	107.4
O3A—C5A—C6A	111.8 (17)	O3B—C5B—C6B	112.7 (18)
O4A—C5A—H5A	108.2	O4B—C5B—H5B	107.4
O4A—C5A—C6A	112.3 (17)	O4B—C5B—C6B	114.4 (17)
C6A—C5A—H5A	108.2	C6B—C5B—H5B	107.4
O2A—C6A—C5A	111.7 (12)	C12B—C11B—H11B	106.7
O2A—C6A—C1A	109.3 (17)	C12B—C11B—C7B	110.6 (17)
O2A—C6A—C7A	103.8 (17)	C13B—C11B—H11B	106.7
C1A—C6A—C5A	108.9 (16)	C13B—C11B—C12B	108.1 (19)
C7A—C6A—C5A	110.0 (18)	C13B—C11B—C7B	117.5 (17)
C7A—C6A—C1A	113.1 (15)	C7B—C11B—H11B	106.7
C6A—C1A—H1A	106.8	O2B—C6B—C5B	112.2 (13)
C6A—C1A—C10A	110.5 (17)	O2B—C6B—C1B	105.8 (17)
C2A—C1A—C6A	114.5 (17)	O2B—C6B—C7B	103.7 (17)
C2A—C1A—H1A	106.8	C1B—C6B—C5B	111.8 (18)
C2A—C1A—C10A	111 (2)	C7B—C6B—C5B	110.0 (19)
C10A—C1A—H1A	106.8	C7B—C6B—C1B	113.0 (14)
C1A—C2A—H2AA	107.8	C6B—C1B—H1B	106.4
C1A—C2A—H2AB	107.8	C6B—C1B—C10B	110.5 (16)
C1A—C2A—C3A	118 (2)	C2B—C1B—C6B	113.5 (15)
H2AA—C2A—H2AB	107.2	C2B—C1B—H1B	106.4
C3A—C2A—H2AA	107.8	C2B—C1B—C10B	113.1 (18)
C3A—C2A—H2AB	107.8	C10B—C1B—H1B	106.4
C4A—C3A—C2A	113.7 (19)	C1B—C2B—H2BA	108.2
C4A—C3A—H3AA	108.8	C1B—C2B—H2BB	108.2
C4A—C3A—H3AB	108.8	C1B—C2B—C3B	116 (2)
C2A—C3A—H3AA	108.8	H2BA—C2B—H2BB	107.4
C2A—C3A—H3AB	108.8	C3B—C2B—H2BA	108.2
H3AA—C3A—H3AB	107.7	C3B—C2B—H2BB	108.2
O4A—C12A—C11A	118 (2)	C4B—C3B—C2B	116.0 (19)
O5A—C12A—O4A	120.4 (17)	C4B—C3B—H3BA	108.3
O5A—C12A—C11A	121 (2)	C4B—C3B—H3BB	108.3
C12A—C11A—H11A	107.3	C2B—C3B—H3BA	108.3
C13A—C11A—C12A	109.6 (19)	C2B—C3B—H3BB	108.3
C13A—C11A—H11A	107.3	H3BA—C3B—H3BB	107.4
C13A—C11A—C7A	115.3 (17)	O4B—C12B—C11B	117 (2)
C7A—C11A—C12A	109.8 (18)	O5B—C12B—O4B	121 (2)
C7A—C11A—H11A	107.3	O5B—C12B—C11B	122 (2)
C11A—C13A—H13A	109.5	C11B—C13B—H13D	109.5
C11A—C13A—H13B	109.5	C11B—C13B—H13E	109.5
C11A—C13A—H13C	109.5	C11B—C13B—H13F	109.5
H13A—C13A—H13B	109.5	H13D—C13B—H13E	109.5
H13A—C13A—H13C	109.5	H13D—C13B—H13F	109.5
H13B—C13A—H13C	109.5	H13E—C13B—H13F	109.5
C6A—C7A—C11A	112.3 (15)	C11B—C7B—H7B	107.6
C6A—C7A—H7A	107.0	C11B—C7B—C8B	111.5 (17)
C6A—C7A—C8A	113.3 (18)	C6B—C7B—C11B	109.6 (16)
C11A—C7A—H7A	107.0	C6B—C7B—H7B	107.6
C8A—C7A—C11A	109.8 (18)	C6B—C7B—C8B	112.9 (18)
C8A—C7A—H7A	107.0	C8B—C7B—H7B	107.6
C7A—C8A—H8AA	109.5	C7B—C8B—H8BA	110.5
C7A—C8A—H8AB	109.5	C7B—C8B—H8BB	110.5
H8AA—C8A—H8AB	108.1	H8BA—C8B—H8BB	108.7
C9A—C8A—C7A	110.8 (18)	C9B—C8B—C7B	106.0 (17)
C9A—C8A—H8AA	109.5	C9B—C8B—H8BA	110.5
C9A—C8A—H8AB	109.5	C9B—C8B—H8BB	110.5
C8A—C9A—H9AA	108.2	C8B—C9B—H9BA	108.5
C8A—C9A—H9AB	108.2	C8B—C9B—H9BB	108.5
H9AA—C9A—H9AB	107.3	C8B—C9B—C10B	115.2 (16)
C10A—C9A—C8A	116.5 (16)	H9BA—C9B—H9BB	107.5
C10A—C9A—H9AA	108.2	C10B—C9B—H9BA	108.5
C10A—C9A—H9AB	108.2	C10B—C9B—H9BB	108.5
C1A—C10A—H10A	106.6	C1B—C10B—H10B	106.2
C9A—C10A—C1A	112 (2)	C9B—C10B—C1B	112.5 (18)
C9A—C10A—H10A	106.6	C9B—C10B—H10B	106.2
C9A—C10A—C14A	112.3 (18)	C14B—C10B—C1B	110.6 (18)
C14A—C10A—C1A	112.6 (19)	C14B—C10B—C9B	114.5 (16)
C14A—C10A—H10A	106.6	C14B—C10B—H10B	106.2
C10A—C14A—H14A	109.5	C10B—C14B—H14D	109.5
C10A—C14A—H14B	109.5	C10B—C14B—H14E	109.5
C10A—C14A—H14C	109.5	C10B—C14B—H14F	109.5
H14A—C14A—H14B	109.5	H14D—C14B—H14E	109.5
H14A—C14A—H14C	109.5	H14D—C14B—H14F	109.5
H14B—C14A—H14C	109.5	H14E—C14B—H14F	109.5

O3A—C4A—C3A—C2A	29 (2)	O3B—C4B—C3B—C2B	29 (2)
O3A—C5A—C6A—O2A	−55 (3)	O3B—C5B—C6B—O2B	−52 (3)
O3A—C5A—C6A—C1A	66.1 (18)	O3B—C5B—C6B—C1B	67 (2)
O3A—C5A—C6A—C7A	−169.4 (14)	O3B—C5B—C6B—C7B	−166.7 (15)
O1A—O2A—C6A—C5A	14 (3)	O1B—O2B—C6B—C5B	10 (3)
O1A—O2A—C6A—C1A	−107.0 (19)	O1B—O2B—C6B—C1B	−112 (2)
O1A—O2A—C6A—C7A	132.1 (17)	O1B—O2B—C6B—C7B	128.4 (19)
O1A—C4A—C3A—C2A	−92 (2)	O1B—C4B—C3B—C2B	−92 (2)
O2A—O1A—C4A—O3A	−74.7 (16)	O2B—O1B—C4B—O3B	−78.4 (17)
O2A—O1A—C4A—C15A	172.4 (14)	O2B—O1B—C4B—C15B	169.8 (17)
O2A—O1A—C4A—C3A	47.0 (16)	O2B—O1B—C4B—C3B	43.2 (18)
O2A—C6A—C1A—C2A	64.1 (19)	O2B—C6B—C1B—C2B	67.3 (19)
O2A—C6A—C1A—C10A	−169.7 (19)	O2B—C6B—C1B—C10B	−164.4 (16)
O2A—C6A—C7A—C11A	−62.6 (18)	O2B—C6B—C7B—C11B	−62.4 (15)
O2A—C6A—C7A—C8A	172.2 (15)	O2B—C6B—C7B—C8B	172.7 (14)
O4A—C5A—C6A—O2A	67 (3)	O4B—C5B—C6B—O2B	71 (3)
O4A—C5A—C6A—C1A	−172.3 (14)	O4B—C5B—C6B—C1B	−170.3 (15)
O4A—C5A—C6A—C7A	−47.8 (17)	O4B—C5B—C6B—C7B	−44 (2)
O4A—C12A—C11A—C13A	164.2 (17)	C15B—C4B—C3B—C2B	149.8 (19)
O4A—C12A—C11A—C7A	37 (2)	C4B—O3B—C5B—O4B	−98.7 (17)
O5A—C12A—C11A—C13A	−19 (3)	C4B—O3B—C5B—C6B	28 (2)
O5A—C12A—C11A—C7A	−146.5 (18)	C4B—O1B—O2B—C6B	51 (2)
C15A—C4A—C3A—C2A	146 (2)	C5B—O3B—C4B—O1B	34 (2)
C4A—O3A—C5A—O4A	−94.3 (16)	C5B—O3B—C4B—C15B	143 (2)
C4A—O3A—C5A—C6A	30 (2)	C5B—O3B—C4B—C3B	−90 (2)
C4A—O1A—O2A—C6A	48 (2)	C5B—O4B—C12B—O5B	151.5 (17)
C5A—O3A—C4A—O1A	31.5 (18)	C5B—O4B—C12B—C11B	−29 (3)
C5A—O3A—C4A—C15A	144.9 (18)	C5B—C6B—C1B—C2B	−55 (2)
C5A—O3A—C4A—C3A	−93.6 (18)	C5B—C6B—C1B—C10B	73 (2)
C5A—O4A—C12A—O5A	150.8 (16)	C5B—C6B—C7B—C11B	57.8 (17)
C5A—O4A—C12A—C11A	−32 (3)	C5B—C6B—C7B—C8B	−67.1 (18)
C5A—C6A—C1A—C2A	−58 (2)	C11B—C7B—C8B—C9B	178.9 (16)
C5A—C6A—C1A—C10A	68 (2)	C6B—C1B—C2B—C3B	−31 (2)
C5A—C6A—C7A—C11A	57.0 (18)	C6B—C1B—C10B—C9B	48 (2)
C5A—C6A—C7A—C8A	−68.1 (17)	C6B—C1B—C10B—C14B	177.6 (15)
C6A—C1A—C2A—C3A	−28 (2)	C6B—C7B—C8B—C9B	−57.3 (19)
C6A—C1A—C10A—C9A	52 (2)	C1B—C6B—C7B—C11B	−176.5 (13)
C6A—C1A—C10A—C14A	179.1 (17)	C1B—C6B—C7B—C8B	58.6 (18)
C6A—C7A—C8A—C9A	−48 (2)	C1B—C2B—C3B—C4B	51 (2)
C1A—C6A—C7A—C11A	179.1 (12)	C2B—C1B—C10B—C9B	176.7 (16)
C1A—C6A—C7A—C8A	53.9 (19)	C2B—C1B—C10B—C14B	−54 (2)
C1A—C2A—C3A—C4A	49 (2)	C12B—O4B—C5B—O3B	156.4 (16)
C2A—C1A—C10A—C9A	179.8 (17)	C12B—O4B—C5B—C6B	31 (3)
C2A—C1A—C10A—C14A	−53 (2)	C12B—C11B—C7B—C6B	−56 (2)
C12A—O4A—C5A—O3A	161.1 (14)	C12B—C11B—C7B—C8B	70 (2)
C12A—O4A—C5A—C6A	37 (2)	C13B—C11B—C12B—O4B	171.2 (17)
C12A—C11A—C7A—C6A	−50 (2)	C13B—C11B—C12B—O5B	−10 (3)
C12A—C11A—C7A—C8A	77 (2)	C13B—C11B—C7B—C6B	179.4 (16)
C11A—C7A—C8A—C9A	−174.8 (15)	C13B—C11B—C7B—C8B	−55 (2)
C13A—C11A—C7A—C6A	−174.2 (14)	C7B—C11B—C12B—O4B	41 (2)
C13A—C11A—C7A—C8A	−47 (2)	C7B—C11B—C12B—O5B	−140 (2)
C7A—C6A—C1A—C2A	179.1 (15)	C7B—C6B—C1B—C2B	−179.9 (13)
C7A—C6A—C1A—C10A	−55 (2)	C7B—C6B—C1B—C10B	−51.6 (19)
C7A—C8A—C9A—C10A	48 (2)	C7B—C8B—C9B—C10B	55 (2)
C8A—C9A—C10A—C1A	−50 (2)	C8B—C9B—C10B—C1B	−53 (2)
C8A—C9A—C10A—C14A	−178.0 (14)	C8B—C9B—C10B—C14B	179.4 (13)
C10A—C1A—C2A—C3A	−153.9 (17)	C10B—C1B—C2B—C3B	−158.1 (16)

Artemisinin (FormIII_7) top

Crystal data top

C₁₅H₂₂O₅	F(000) = 608
M_r = 282.32	D_x = 1.608 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 9.1812 (15) Å	Cell parameters from 720 reflections
b = 13.865 (3) Å	θ = 2.7–23.0°
c = 9.479 (4) Å	µ = 0.12 mm⁻¹
β = 104.89 (3)°	T = 296 K
V = 1166.2 (6) Å³	Prism, clear colourless
Z = 4	0.2 × 0.1 × 0.09 mm

Data collection top

Bruker D8 Venture diffractometer	1332 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	584 reflections with I > 2σ(I)
Mirror optics monochromator	R_int = 0.168
ω scans	θ_max = 23.3°, θ_min = 2.3°
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1498 before and 0.0938 after correction. The Ratio of minimum to maximum transmission is 0.5260. The λ/2 correction factor is Not present.	h = −10→10
T_min = 0.392, T_max = 0.745	k = −15→15
5516 measured reflections	l = −4→4

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.092	w = 1/[σ²(F_o²) + (0.1206P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.256	(Δ/σ)_max < 0.001
S = 0.97	Δρ_max = 0.25 e Å⁻³
1332 reflections	Δρ_min = −0.30 e Å⁻³
167 parameters	Absolute structure: Flack x determined using 182 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
47 restraints	Absolute structure parameter: −1.1 (10)

Special details top

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

	x	y	z	U_iso*/U_eq
O3A	0.7953 (17)	0.3109 (12)	0.719 (4)	0.034 (6)*
O1A	1.0218 (19)	0.2290 (11)	0.808 (4)	0.036 (6)*
O2A	1.1126 (16)	0.3139 (10)	0.865 (4)	0.037 (5)*
O4A	0.8325 (18)	0.3108 (13)	0.970 (4)	0.037 (6)*
O5A	0.849 (2)	0.3102 (13)	1.208 (5)	0.043 (6)*
C15A	0.837 (3)	0.1596 (17)	0.623 (8)	0.046 (10)*
H15A	0.778671	0.137062	0.686921	0.070*
H15B	0.913634	0.112976	0.619761	0.070*
H15C	0.772884	0.168661	0.526788	0.070*
C4A	0.911 (2)	0.2545 (15)	0.679 (3)	0.037 (9)*
C5A	0.851 (2)	0.3663 (19)	0.846 (4)	0.032 (9)*
H5A	0.789023	0.424613	0.837942	0.039*
C6A	1.015 (2)	0.3970 (12)	0.862 (4)	0.023 (8)*
C1A	1.024 (3)	0.4655 (15)	0.738 (5)	0.023 (7)*
H1A	1.131042	0.479534	0.748745	0.027*
C2A	0.961 (3)	0.4242 (14)	0.586 (5)	0.034 (9)*
H2AA	1.012686	0.454537	0.520072	0.041*
H2AB	0.855363	0.441534	0.552933	0.041*
C3A	0.975 (3)	0.3141 (14)	0.573 (5)	0.036 (9)*
H3AA	0.923529	0.295032	0.474326	0.043*
H3AB	1.080575	0.297975	0.588214	0.043*
C12A	0.906 (3)	0.329 (2)	1.110 (5)	0.038 (11)*
C11A	1.066 (3)	0.369 (2)	1.138 (5)	0.047 (10)*
H11A	1.131131	0.313590	1.133075	0.057*
C13A	1.120 (3)	0.410 (2)	1.292 (5)	0.053 (11)*
H13A	1.037609	0.442077	1.318093	0.079*
H13B	1.200033	0.454796	1.296147	0.079*
H13C	1.155321	0.358213	1.360125	0.079*
C7A	1.080 (3)	0.4384 (13)	1.015 (4)	0.016 (7)*
H7A	1.188030	0.449020	1.026061	0.019*
C8A	1.010 (4)	0.5370 (15)	1.035 (6)	0.053 (11)*
H8AA	0.907882	0.527269	1.042723	0.063*
H8AB	1.067440	0.566229	1.125011	0.063*
C9A	1.008 (3)	0.6056 (18)	0.908 (5)	0.026 (8)*
H9AA	0.947141	0.661420	0.917390	0.031*
H9AB	1.109572	0.627963	0.916106	0.031*
C10A	0.946 (3)	0.5621 (15)	0.756 (5)	0.030 (8)*
H10A	0.838817	0.548205	0.745218	0.035*
C14A	0.956 (3)	0.6325 (19)	0.635 (5)	0.031 (9)*
H14A	1.058656	0.635853	0.628468	0.047*
H14B	0.924093	0.695335	0.657558	0.047*
H14C	0.892658	0.610664	0.544164	0.047*
O3B	0.3093 (18)	0.0070 (13)	0.714 (4)	0.035 (6)*
O1B	0.5588 (19)	−0.0393 (11)	0.797 (4)	0.036 (6)*
O2B	0.6177 (17)	0.0590 (10)	0.834 (4)	0.034 (6)*
O4B	0.350 (2)	0.0135 (14)	0.965 (4)	0.037 (6)*
O5B	0.387 (2)	0.0165 (14)	1.208 (5)	0.049 (7)*
C15B	0.405 (3)	−0.1329 (16)	0.637 (8)	0.043 (9)*
H15D	0.354225	−0.159784	0.704412	0.065*
H15E	0.497819	−0.166932	0.644359	0.065*
H15F	0.342011	−0.138939	0.539236	0.065*
C4B	0.438 (2)	−0.0281 (15)	0.672 (4)	0.028 (8)*
C5B	0.348 (2)	0.0680 (18)	0.835 (4)	0.022 (7)*
H5B	0.267653	0.116387	0.823942	0.026*
C11B	0.574 (3)	0.0941 (17)	1.121 (5)	0.030 (8)*
H11B	0.648703	0.048015	1.103904	0.036*
C6B	0.497 (2)	0.1218 (13)	0.854 (4)	0.015 (7)*
C1B	0.485 (3)	0.1913 (14)	0.727 (4)	0.023 (7)*
H1B	0.586959	0.214702	0.733123	0.028*
C2B	0.428 (3)	0.1445 (13)	0.578 (5)	0.022 (8)*
H2BA	0.462784	0.183624	0.508025	0.027*
H2BB	0.318889	0.148294	0.551322	0.027*
C3B	0.471 (3)	0.0395 (12)	0.557 (4)	0.030 (9)*
H3BA	0.415833	0.017660	0.460745	0.036*
H3BB	0.577786	0.036407	0.561194	0.036*
C12B	0.427 (3)	0.0391 (19)	1.101 (5)	0.044 (11)*
C13B	0.631 (3)	0.130 (2)	1.277 (5)	0.030 (8)*
H13D	0.549474	0.158756	1.307718	0.045*
H13E	0.708880	0.176950	1.281215	0.045*
H13F	0.670964	0.076671	1.339430	0.045*
C7B	0.555 (2)	0.1716 (14)	1.001 (4)	0.022 (7)*
H7B	0.654301	0.198698	1.005306	0.026*
C8B	0.451 (3)	0.2547 (15)	1.021 (5)	0.029 (8)*
H8BA	0.351616	0.230212	1.020680	0.035*
H8BB	0.492125	0.287646	1.112848	0.035*
C9B	0.440 (3)	0.3233 (19)	0.893 (5)	0.038 (9)*
H9BA	0.538949	0.351861	0.903558	0.045*
H9BB	0.371867	0.375076	0.901324	0.045*
C10B	0.388 (3)	0.2806 (17)	0.740 (5)	0.045 (10)*
H10B	0.285179	0.257173	0.729514	0.054*
C14B	0.381 (3)	0.353 (2)	0.616 (6)	0.040 (9)*
H14D	0.480766	0.373265	0.616886	0.060*
H14E	0.322142	0.407854	0.629805	0.060*
H14F	0.334401	0.322839	0.524433	0.060*

Geometric parameters (Å, º) top

O3A—C4A	1.443 (14)	O3B—C4B	1.428 (14)
O3A—C5A	1.408 (15)	O3B—C5B	1.397 (15)
O1A—O2A	1.462 (14)	O1B—O2B	1.473 (13)
O1A—C4A	1.416 (15)	O1B—C4B	1.413 (15)
O2A—C6A	1.458 (14)	O2B—C6B	1.463 (14)
O4A—C5A	1.450 (15)	O4B—C5B	1.439 (15)
O4A—C12A	1.350 (15)	O4B—C12B	1.345 (15)
O5A—C12A	1.210 (15)	O5B—C12B	1.212 (15)
C15A—H15A	0.9600	C15B—H15D	0.9600
C15A—H15B	0.9600	C15B—H15E	0.9600
C15A—H15C	0.9600	C15B—H15F	0.9600
C15A—C4A	1.513 (15)	C15B—C4B	1.504 (15)
C4A—C3A	1.532 (15)	C4B—C3B	1.524 (15)
C5A—H5A	0.9800	C5B—H5B	0.9800
C5A—C6A	1.533 (14)	C5B—C6B	1.529 (14)
C6A—C1A	1.531 (15)	C11B—H11B	0.9800
C6A—C7A	1.531 (15)	C11B—C12B	1.516 (15)
C1A—H1A	0.9800	C11B—C13B	1.520 (15)
C1A—C2A	1.524 (15)	C11B—C7B	1.537 (15)
C1A—C10A	1.551 (14)	C6B—C1B	1.524 (15)
C2A—H2AA	0.9700	C6B—C7B	1.526 (15)
C2A—H2AB	0.9700	C1B—H1B	0.9800
C2A—C3A	1.540 (14)	C1B—C2B	1.522 (15)
C3A—H3AA	0.9700	C1B—C10B	1.547 (14)
C3A—H3AB	0.9700	C2B—H2BA	0.9700
C12A—C11A	1.522 (15)	C2B—H2BB	0.9700
C11A—H11A	0.9800	C2B—C3B	1.536 (14)
C11A—C13A	1.532 (15)	C3B—H3BA	0.9700
C11A—C7A	1.543 (15)	C3B—H3BB	0.9700
C13A—H13A	0.9600	C13B—H13D	0.9600
C13A—H13B	0.9600	C13B—H13E	0.9600
C13A—H13C	0.9600	C13B—H13F	0.9600
C7A—H7A	0.9800	C7B—H7B	0.9800
C7A—C8A	1.542 (14)	C7B—C8B	1.538 (14)
C8A—H8AA	0.9700	C8B—H8BA	0.9700
C8A—H8AB	0.9700	C8B—H8BB	0.9700
C8A—C9A	1.528 (15)	C8B—C9B	1.523 (15)
C9A—H9AA	0.9700	C9B—H9BA	0.9700
C9A—H9AB	0.9700	C9B—H9BB	0.9700
C9A—C10A	1.528 (15)	C9B—C10B	1.527 (15)
C10A—H10A	0.9800	C10B—H10B	0.9800
C10A—C14A	1.528 (15)	C10B—C14B	1.533 (15)
C14A—H14A	0.9600	C14B—H14D	0.9600
C14A—H14B	0.9600	C14B—H14E	0.9600
C14A—H14C	0.9600	C14B—H14F	0.9600

C5A—O3A—C4A	112.8 (19)	C5B—O3B—C4B	113 (2)
C4A—O1A—O2A	109.3 (19)	C4B—O1B—O2B	105 (2)
C6A—O2A—O1A	109.9 (15)	C6B—O2B—O1B	109.6 (13)
C12A—O4A—C5A	124 (2)	C12B—O4B—C5B	125 (2)
H15A—C15A—H15B	109.5	H15D—C15B—H15E	109.5
H15A—C15A—H15C	109.5	H15D—C15B—H15F	109.5
H15B—C15A—H15C	109.5	H15E—C15B—H15F	109.5
C4A—C15A—H15A	109.5	C4B—C15B—H15D	109.5
C4A—C15A—H15B	109.5	C4B—C15B—H15E	109.5
C4A—C15A—H15C	109.5	C4B—C15B—H15F	109.5
O3A—C4A—C15A	106 (2)	O3B—C4B—C15B	105 (2)
O3A—C4A—C3A	108 (2)	O3B—C4B—C3B	109 (2)
O1A—C4A—O3A	109 (2)	O1B—C4B—O3B	109.0 (19)
O1A—C4A—C15A	104 (3)	O1B—C4B—C15B	99 (3)
O1A—C4A—C3A	113 (2)	O1B—C4B—C3B	114 (2)
C15A—C4A—C3A	117 (3)	C15B—C4B—C3B	120 (3)
O3A—C5A—O4A	108 (2)	O3B—C5B—O4B	109 (2)
O3A—C5A—H5A	108.2	O3B—C5B—H5B	107.5
O3A—C5A—C6A	112 (2)	O3B—C5B—C6B	115 (2)
O4A—C5A—H5A	108.2	O4B—C5B—H5B	107.5
O4A—C5A—C6A	112 (2)	O4B—C5B—C6B	110 (2)
C6A—C5A—H5A	108.2	C6B—C5B—H5B	107.5
O2A—C6A—C5A	111.5 (17)	C12B—C11B—H11B	106.8
O2A—C6A—C1A	110 (2)	C12B—C11B—C13B	111 (3)
O2A—C6A—C7A	101 (2)	C12B—C11B—C7B	109 (2)
C5A—C6A—C1A	110 (2)	C13B—C11B—H11B	106.8
C5A—C6A—C7A	110 (2)	C13B—C11B—C7B	116 (2)
C1A—C6A—C7A	114.1 (19)	C7B—C11B—H11B	106.8
C6A—C1A—H1A	107.3	O2B—C6B—C5B	112.4 (16)
C6A—C1A—C10A	109 (2)	O2B—C6B—C1B	100 (2)
C2A—C1A—C6A	114 (2)	O2B—C6B—C7B	107 (2)
C2A—C1A—H1A	107.3	C1B—C6B—C5B	110 (2)
C2A—C1A—C10A	111 (3)	C7B—C6B—C5B	115 (2)
C10A—C1A—H1A	107.3	C7B—C6B—C1B	112.0 (18)
C1A—C2A—H2AA	108.4	C6B—C1B—H1B	106.9
C1A—C2A—H2AB	108.4	C6B—C1B—C10B	112 (2)
C1A—C2A—C3A	115 (3)	C2B—C1B—C6B	114 (2)
H2AA—C2A—H2AB	107.5	C2B—C1B—H1B	106.9
C3A—C2A—H2AA	108.4	C2B—C1B—C10B	110 (2)
C3A—C2A—H2AB	108.4	C10B—C1B—H1B	106.9
C4A—C3A—C2A	115 (2)	C1B—C2B—H2BA	107.5
C4A—C3A—H3AA	108.4	C1B—C2B—H2BB	107.5
C4A—C3A—H3AB	108.4	C1B—C2B—C3B	119 (3)
C2A—C3A—H3AA	108.4	H2BA—C2B—H2BB	107.0
C2A—C3A—H3AB	108.4	C3B—C2B—H2BA	107.5
H3AA—C3A—H3AB	107.5	C3B—C2B—H2BB	107.5
O4A—C12A—C11A	117 (3)	C4B—C3B—C2B	113 (2)
O5A—C12A—O4A	121 (2)	C4B—C3B—H3BA	109.1
O5A—C12A—C11A	122 (3)	C4B—C3B—H3BB	109.1
C12A—C11A—H11A	106.4	C2B—C3B—H3BA	109.1
C12A—C11A—C13A	111 (3)	C2B—C3B—H3BB	109.1
C12A—C11A—C7A	111 (3)	H3BA—C3B—H3BB	107.8
C13A—C11A—H11A	106.4	O4B—C12B—C11B	119 (3)
C13A—C11A—C7A	115 (3)	O5B—C12B—O4B	122 (3)
C7A—C11A—H11A	106.4	O5B—C12B—C11B	119 (3)
C11A—C13A—H13A	109.5	C11B—C13B—H13D	109.5
C11A—C13A—H13B	109.5	C11B—C13B—H13E	109.5
C11A—C13A—H13C	109.5	C11B—C13B—H13F	109.5
H13A—C13A—H13B	109.5	H13D—C13B—H13E	109.5
H13A—C13A—H13C	109.5	H13D—C13B—H13F	109.5
H13B—C13A—H13C	109.5	H13E—C13B—H13F	109.5
C6A—C7A—C11A	113 (2)	C11B—C7B—H7B	108.1
C6A—C7A—H7A	107.2	C6B—C7B—C11B	108 (2)
C6A—C7A—C8A	112 (3)	C6B—C7B—H7B	108.1
C11A—C7A—H7A	107.2	C6B—C7B—C8B	112 (2)
C8A—C7A—C11A	110 (3)	C8B—C7B—C11B	113 (2)
C8A—C7A—H7A	107.2	C8B—C7B—H7B	108.1
C7A—C8A—H8AA	109.1	C7B—C8B—H8BA	110.4
C7A—C8A—H8AB	109.1	C7B—C8B—H8BB	110.4
H8AA—C8A—H8AB	107.9	H8BA—C8B—H8BB	108.6
C9A—C8A—C7A	112 (3)	C9B—C8B—C7B	107 (2)
C9A—C8A—H8AA	109.1	C9B—C8B—H8BA	110.4
C9A—C8A—H8AB	109.1	C9B—C8B—H8BB	110.4
C8A—C9A—H9AA	108.5	C8B—C9B—H9BA	108.1
C8A—C9A—H9AB	108.5	C8B—C9B—H9BB	108.1
H9AA—C9A—H9AB	107.5	C8B—C9B—C10B	117 (2)
C10A—C9A—C8A	115 (2)	H9BA—C9B—H9BB	107.3
C10A—C9A—H9AA	108.5	C10B—C9B—H9BA	108.1
C10A—C9A—H9AB	108.5	C10B—C9B—H9BB	108.1
C1A—C10A—H10A	107.4	C1B—C10B—H10B	106.6
C9A—C10A—C1A	112 (3)	C9B—C10B—C1B	110 (3)
C9A—C10A—H10A	107.4	C9B—C10B—H10B	106.6
C14A—C10A—C1A	110 (2)	C9B—C10B—C14B	115 (3)
C14A—C10A—C9A	112 (2)	C14B—C10B—C1B	112 (2)
C14A—C10A—H10A	107.4	C14B—C10B—H10B	106.6
C10A—C14A—H14A	109.5	C10B—C14B—H14D	109.5
C10A—C14A—H14B	109.5	C10B—C14B—H14E	109.5
C10A—C14A—H14C	109.5	C10B—C14B—H14F	109.5
H14A—C14A—H14B	109.5	H14D—C14B—H14E	109.5
H14A—C14A—H14C	109.5	H14D—C14B—H14F	109.5
H14B—C14A—H14C	109.5	H14E—C14B—H14F	109.5

O3A—C4A—C3A—C2A	26 (3)	O3B—C4B—C3B—C2B	32 (3)
O3A—C5A—C6A—O2A	−57 (4)	O3B—C5B—C6B—O2B	−45 (4)
O3A—C5A—C6A—C1A	65 (3)	O3B—C5B—C6B—C1B	65 (3)
O3A—C5A—C6A—C7A	−168.4 (19)	O3B—C5B—C6B—C7B	−167.9 (19)
O1A—O2A—C6A—C5A	17 (4)	O1B—O2B—C6B—C5B	1 (4)
O1A—O2A—C6A—C1A	−106 (3)	O1B—O2B—C6B—C1B	−115 (3)
O1A—O2A—C6A—C7A	133 (2)	O1B—O2B—C6B—C7B	128 (3)
O1A—C4A—C3A—C2A	−95 (3)	O1B—C4B—C3B—C2B	−91 (3)
O2A—O1A—C4A—O3A	−74 (2)	O2B—O1B—C4B—O3B	−78 (2)
O2A—O1A—C4A—C15A	174 (2)	O2B—O1B—C4B—C15B	173 (2)
O2A—O1A—C4A—C3A	47 (2)	O2B—O1B—C4B—C3B	44 (2)
O2A—C6A—C1A—C2A	66 (2)	O2B—C6B—C1B—C2B	67 (2)
O2A—C6A—C1A—C10A	−169 (3)	O2B—C6B—C1B—C10B	−167 (2)
O2A—C6A—C7A—C11A	−63 (2)	O2B—C6B—C7B—C11B	−67 (2)
O2A—C6A—C7A—C8A	172 (2)	O2B—C6B—C7B—C8B	168 (2)
O4A—C5A—C6A—O2A	64 (4)	O4B—C5B—C6B—O2B	78 (3)
O4A—C5A—C6A—C1A	−173.0 (19)	O4B—C5B—C6B—C1B	−171.3 (18)
O4A—C5A—C6A—C7A	−47 (2)	O4B—C5B—C6B—C7B	−44 (3)
O4A—C12A—C11A—C13A	165 (3)	C15B—C4B—C3B—C2B	152 (3)
O4A—C12A—C11A—C7A	36 (4)	C4B—O3B—C5B—O4B	−97 (2)
O5A—C12A—C11A—C13A	−17 (4)	C4B—O3B—C5B—C6B	27 (3)
O5A—C12A—C11A—C7A	−147 (3)	C4B—O1B—O2B—C6B	57 (3)
C15A—C4A—C3A—C2A	145 (3)	C5B—O3B—C4B—O1B	33 (3)
C4A—O3A—C5A—O4A	−93 (2)	C5B—O3B—C4B—C15B	138 (3)
C4A—O3A—C5A—C6A	31 (3)	C5B—O3B—C4B—C3B	−92 (3)
C4A—O1A—O2A—C6A	45 (3)	C5B—O4B—C12B—O5B	151 (2)
C5A—O3A—C4A—O1A	31 (2)	C5B—O4B—C12B—C11B	−32 (4)
C5A—O3A—C4A—C15A	142 (3)	C5B—C6B—C1B—C2B	−52 (2)
C5A—O3A—C4A—C3A	−92 (3)	C5B—C6B—C1B—C10B	74 (3)
C5A—O4A—C12A—O5A	150 (2)	C5B—C6B—C7B—C11B	58 (2)
C5A—O4A—C12A—C11A	−33 (4)	C5B—C6B—C7B—C8B	−66 (2)
C5A—C6A—C1A—C2A	−57 (3)	C11B—C7B—C8B—C9B	−179 (2)
C5A—C6A—C1A—C10A	68 (3)	C6B—C1B—C2B—C3B	−34 (3)
C5A—C6A—C7A—C11A	55 (2)	C6B—C1B—C10B—C9B	49 (3)
C5A—C6A—C7A—C8A	−70 (2)	C6B—C1B—C10B—C14B	178 (2)
C6A—C1A—C2A—C3A	−30 (3)	C6B—C7B—C8B—C9B	−57 (3)
C6A—C1A—C10A—C9A	53 (3)	C1B—C6B—C7B—C11B	−175.7 (16)
C6A—C1A—C10A—C14A	179 (2)	C1B—C6B—C7B—C8B	60 (2)
C6A—C7A—C8A—C9A	−48 (3)	C1B—C2B—C3B—C4B	51 (3)
C1A—C6A—C7A—C11A	178.7 (16)	C2B—C1B—C10B—C9B	177 (2)
C1A—C6A—C7A—C8A	54 (3)	C2B—C1B—C10B—C14B	−55 (3)
C1A—C2A—C3A—C4A	53 (3)	C12B—O4B—C5B—O3B	157 (2)
C2A—C1A—C10A—C9A	−180 (2)	C12B—O4B—C5B—C6B	31 (3)
C2A—C1A—C10A—C14A	−54 (3)	C12B—C11B—C7B—C6B	−54 (3)
C12A—O4A—C5A—O3A	162 (2)	C12B—C11B—C7B—C8B	70 (3)
C12A—O4A—C5A—C6A	38 (3)	C13B—C11B—C12B—O4B	171 (2)
C12A—C11A—C7A—C6A	−49 (3)	C13B—C11B—C12B—O5B	−12 (4)
C12A—C11A—C7A—C8A	77 (3)	C13B—C11B—C7B—C6B	−180 (2)
C11A—C7A—C8A—C9A	−174 (2)	C13B—C11B—C7B—C8B	−56 (3)
C13A—C11A—C7A—C6A	−176 (2)	C7B—C11B—C12B—O4B	42 (3)
C13A—C11A—C7A—C8A	−50 (3)	C7B—C11B—C12B—O5B	−140 (3)
C7A—C6A—C1A—C2A	179.2 (18)	C7B—C6B—C1B—C2B	179.7 (17)
C7A—C6A—C1A—C10A	−56 (3)	C7B—C6B—C1B—C10B	−54 (3)
C7A—C8A—C9A—C10A	48 (3)	C7B—C8B—C9B—C10B	56 (3)
C8A—C9A—C10A—C1A	−52 (3)	C8B—C9B—C10B—C1B	−52 (3)
C8A—C9A—C10A—C14A	−176.3 (18)	C8B—C9B—C10B—C14B	−180 (2)
C10A—C1A—C2A—C3A	−155 (2)	C10B—C1B—C2B—C3B	−161 (2)

Artemisinin (FormIII_8) top

Crystal data top

C₁₅H₂₂O₅	F(000) = 608
M_r = 282.32	D_x = 1.533 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 9.3601 (11) Å	Cell parameters from 889 reflections
b = 14.1006 (18) Å	θ = 2.7–22.6°
c = 9.587 (3) Å	µ = 0.11 mm⁻¹
β = 104.87 (2)°	T = 296 K
V = 1222.9 (5) Å³	Prism, clear colourless
Z = 4	0.2 × 0.1 × 0.09 mm

Data collection top

Bruker D8 Venture diffractometer	1324 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	644 reflections with I > 2σ(I)
Mirror optics monochromator	R_int = 0.120
ω scans	θ_max = 23.3°, θ_min = 2.3°
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0853 before and 0.0632 after correction. The Ratio of minimum to maximum transmission is 0.8841. The λ/2 correction factor is Not present.	h = −10→10
T_min = 0.659, T_max = 0.745	k = −15→15
6478 measured reflections	l = −4→4

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.066	w = 1/[σ²(F_o²) + (0.0644P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.149	(Δ/σ)_max < 0.001
S = 0.98	Δρ_max = 0.16 e Å⁻³
1324 reflections	Δρ_min = −0.15 e Å⁻³
167 parameters	Absolute structure: Flack x determined using 213 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
47 restraints	Absolute structure parameter: −1.4 (10)

Special details top

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

	x	y	z	U_iso*/U_eq
O3A	0.7983 (12)	0.3092 (9)	0.724 (3)	0.047 (4)*
O1A	1.0199 (14)	0.2285 (7)	0.809 (3)	0.038 (4)*
O2A	1.1075 (11)	0.3134 (6)	0.859 (3)	0.032 (4)*
O4A	0.8312 (13)	0.3109 (8)	0.969 (3)	0.041 (4)*
O5A	0.8527 (14)	0.3077 (9)	1.205 (4)	0.048 (5)*
C15A	0.833 (2)	0.1626 (11)	0.623 (4)	0.047 (6)*
H15A	0.819534	0.123370	0.700418	0.071*
H15B	0.892847	0.129670	0.570913	0.071*
H15C	0.738494	0.176853	0.558852	0.071*
C4A	0.9087 (18)	0.2537 (11)	0.684 (3)	0.042 (7)*
C5A	0.8531 (16)	0.3649 (12)	0.847 (3)	0.032 (6)*
H5A	0.792439	0.422323	0.837906	0.038*
C6A	1.0139 (16)	0.3953 (10)	0.865 (4)	0.032 (6)*
C1A	1.024 (2)	0.4621 (11)	0.743 (4)	0.040 (6)*
H1A	1.129226	0.475416	0.753625	0.048*
C2A	0.963 (2)	0.4218 (11)	0.590 (4)	0.048 (7)*
H2AA	1.018394	0.449259	0.527532	0.058*
H2AB	0.861171	0.442197	0.555114	0.058*
C3A	0.968 (2)	0.3130 (11)	0.577 (4)	0.049 (6)*
H3AA	0.912864	0.295830	0.480407	0.059*
H3AB	1.070052	0.294703	0.587003	0.059*
C12A	0.907 (2)	0.3273 (14)	1.107 (4)	0.047 (9)*
C11A	1.062 (2)	0.3684 (15)	1.132 (4)	0.049 (7)*
H11A	1.126704	0.314740	1.124670	0.059*
C13A	1.117 (2)	0.4059 (16)	1.286 (4)	0.064 (8)*
H13A	1.041242	0.444154	1.309114	0.096*
H13B	1.204085	0.443588	1.294012	0.096*
H13C	1.139716	0.353517	1.352039	0.096*
C7A	1.077 (2)	0.4388 (10)	1.014 (3)	0.035 (6)*
H7A	1.182819	0.450972	1.024766	0.042*
C8A	1.002 (2)	0.5333 (11)	1.029 (4)	0.049 (7)*
H8AA	1.050714	0.562540	1.120139	0.059*
H8AB	0.899620	0.521830	1.028354	0.059*
C9A	1.008 (2)	0.6006 (14)	0.905 (4)	0.043 (7)*
H9AA	0.951918	0.657316	0.912792	0.052*
H9AB	1.109917	0.619553	0.915408	0.052*
C10A	0.948 (2)	0.5581 (10)	0.755 (4)	0.041 (6)*
H10A	0.842572	0.545274	0.743265	0.049*
C14A	0.9608 (19)	0.6277 (13)	0.638 (4)	0.048 (7)*
H14A	1.060709	0.628236	0.628910	0.072*
H14B	0.934263	0.690056	0.662300	0.072*
H14C	0.895507	0.608624	0.547437	0.072*
O3B	0.3116 (12)	0.0081 (8)	0.721 (3)	0.034 (4)*
O1B	0.5573 (14)	−0.0361 (7)	0.801 (3)	0.044 (4)*
O2B	0.6146 (12)	0.0603 (7)	0.839 (3)	0.040 (4)*
O4B	0.3482 (13)	0.0173 (9)	0.968 (3)	0.037 (4)*
O5B	0.3878 (15)	0.0168 (10)	1.205 (4)	0.051 (5)*
C15B	0.401 (2)	−0.1265 (11)	0.626 (5)	0.046 (7)*
H15D	0.376627	−0.163220	0.701008	0.069*
H15E	0.485867	−0.154036	0.602165	0.069*
H15F	0.319198	−0.126208	0.542258	0.069*
C4B	0.4368 (18)	−0.0263 (11)	0.678 (3)	0.041 (6)*
C5B	0.3497 (16)	0.0708 (13)	0.839 (3)	0.034 (6)*
H5B	0.270902	0.118325	0.825260	0.041*
C11B	0.5704 (19)	0.0960 (12)	1.117 (4)	0.034 (6)*
H11B	0.644324	0.050537	1.102317	0.040*
C6B	0.4939 (16)	0.1238 (10)	0.850 (3)	0.033 (6)*
C1B	0.482 (2)	0.1928 (10)	0.726 (3)	0.032 (6)*
H1B	0.582077	0.216348	0.730832	0.038*
C2B	0.425 (2)	0.1451 (10)	0.580 (4)	0.040 (6)*
H2BA	0.456960	0.182251	0.508741	0.048*
H2BB	0.317608	0.147722	0.555494	0.048*
C3B	0.4704 (19)	0.0417 (9)	0.567 (4)	0.036 (7)*
H3BA	0.420443	0.018969	0.470996	0.044*
H3BB	0.575841	0.039994	0.574544	0.044*
C12B	0.427 (2)	0.0420 (12)	1.101 (3)	0.040 (8)*
C13B	0.622 (2)	0.1313 (13)	1.272 (4)	0.044 (7)*
H13D	0.544453	0.166911	1.296166	0.067*
H13E	0.707456	0.171051	1.281846	0.067*
H13F	0.647464	0.078034	1.336221	0.067*
C7B	0.5508 (19)	0.1709 (11)	0.997 (3)	0.032 (6)*
H7B	0.649013	0.196585	1.001114	0.038*
C8B	0.452 (2)	0.2552 (11)	1.015 (4)	0.043 (6)*
H8BA	0.354316	0.232453	1.017086	0.052*
H8BB	0.494346	0.288115	1.104774	0.052*
C9B	0.4391 (19)	0.3221 (12)	0.888 (3)	0.037 (6)*
H9BA	0.535541	0.350001	0.895877	0.044*
H9BB	0.372584	0.373254	0.896909	0.044*
C10B	0.385 (2)	0.2792 (10)	0.738 (3)	0.036 (6)*
H10B	0.283250	0.256738	0.726198	0.043*
C14B	0.3829 (18)	0.3535 (14)	0.621 (4)	0.047 (6)*
H14D	0.482498	0.370773	0.622957	0.070*
H14E	0.330209	0.408633	0.639452	0.070*
H14F	0.334760	0.327818	0.528376	0.070*

Geometric parameters (Å, º) top

O3A—C4A	1.428 (13)	O3B—C4B	1.424 (13)
O3A—C5A	1.398 (14)	O3B—C5B	1.405 (14)
O1A—O2A	1.460 (12)	O1B—O2B	1.474 (11)
O1A—C4A	1.419 (15)	O1B—C4B	1.411 (15)
O2A—C6A	1.459 (12)	O2B—C6B	1.467 (13)
O4A—C5A	1.451 (14)	O4B—C5B	1.452 (14)
O4A—C12A	1.348 (15)	O4B—C12B	1.344 (14)
O5A—C12A	1.206 (14)	O5B—C12B	1.207 (15)
C15A—H15A	0.9600	C15B—H15D	0.9600
C15A—H15B	0.9600	C15B—H15E	0.9600
C15A—H15C	0.9600	C15B—H15F	0.9600
C15A—C4A	1.510 (14)	C15B—C4B	1.506 (14)
C4A—C3A	1.530 (15)	C4B—C3B	1.528 (15)
C5A—H5A	0.9800	C5B—H5B	0.9800
C5A—C6A	1.532 (13)	C5B—C6B	1.522 (13)
C6A—C1A	1.530 (14)	C11B—H11B	0.9800
C6A—C7A	1.522 (15)	C11B—C12B	1.515 (14)
C1A—H1A	0.9800	C11B—C13B	1.524 (15)
C1A—C2A	1.533 (15)	C11B—C7B	1.535 (15)
C1A—C10A	1.549 (13)	C6B—C1B	1.522 (14)
C2A—H2AA	0.9700	C6B—C7B	1.526 (15)
C2A—H2AB	0.9700	C1B—H1B	0.9800
C2A—C3A	1.541 (13)	C1B—C2B	1.519 (15)
C3A—H3AA	0.9700	C1B—C10B	1.544 (13)
C3A—H3AB	0.9700	C2B—H2BA	0.9700
C12A—C11A	1.527 (14)	C2B—H2BB	0.9700
C11A—H11A	0.9800	C2B—C3B	1.534 (13)
C11A—C13A	1.532 (15)	C3B—H3BA	0.9700
C11A—C7A	1.538 (15)	C3B—H3BB	0.9700
C13A—H13A	0.9600	C13B—H13D	0.9600
C13A—H13B	0.9600	C13B—H13E	0.9600
C13A—H13C	0.9600	C13B—H13F	0.9600
C7A—H7A	0.9800	C7B—H7B	0.9800
C7A—C8A	1.533 (13)	C7B—C8B	1.544 (13)
C8A—H8AA	0.9700	C8B—H8BA	0.9700
C8A—H8AB	0.9700	C8B—H8BB	0.9700
C8A—C9A	1.533 (15)	C8B—C9B	1.520 (15)
C9A—H9AA	0.9700	C9B—H9BA	0.9700
C9A—H9AB	0.9700	C9B—H9BB	0.9700
C9A—C10A	1.524 (15)	C9B—C10B	1.527 (15)
C10A—H10A	0.9800	C10B—H10B	0.9800
C10A—C14A	1.523 (15)	C10B—C14B	1.527 (15)
C14A—H14A	0.9600	C14B—H14D	0.9600
C14A—H14B	0.9600	C14B—H14E	0.9600
C14A—H14C	0.9600	C14B—H14F	0.9600

C5A—O3A—C4A	113.8 (14)	C5B—O3B—C4B	112.9 (14)
C4A—O1A—O2A	107.6 (13)	C4B—O1B—O2B	106.3 (14)
C6A—O2A—O1A	111.7 (10)	C6B—O2B—O1B	110.1 (10)
C12A—O4A—C5A	123.4 (14)	C12B—O4B—C5B	123.3 (14)
H15A—C15A—H15B	109.5	H15D—C15B—H15E	109.5
H15A—C15A—H15C	109.5	H15D—C15B—H15F	109.5
H15B—C15A—H15C	109.5	H15E—C15B—H15F	109.5
C4A—C15A—H15A	109.5	C4B—C15B—H15D	109.5
C4A—C15A—H15B	109.5	C4B—C15B—H15E	109.5
C4A—C15A—H15C	109.5	C4B—C15B—H15F	109.5
O3A—C4A—C15A	105.7 (15)	O3B—C4B—C15B	106.7 (14)
O3A—C4A—C3A	107.1 (16)	O3B—C4B—C3B	108.7 (16)
O1A—C4A—O3A	109.3 (16)	O1B—C4B—O3B	109.5 (15)
O1A—C4A—C15A	106.5 (18)	O1B—C4B—C15B	104 (2)
O1A—C4A—C3A	112.9 (16)	O1B—C4B—C3B	112.3 (15)
C15A—C4A—C3A	115.0 (19)	C15B—C4B—C3B	115.2 (18)
O3A—C5A—O4A	106.6 (16)	O3B—C5B—O4B	107.5 (16)
O3A—C5A—H5A	108.0	O3B—C5B—H5B	107.3
O3A—C5A—C6A	112.9 (17)	O3B—C5B—C6B	113.9 (17)
O4A—C5A—H5A	108.0	O4B—C5B—H5B	107.3
O4A—C5A—C6A	113.2 (17)	O4B—C5B—C6B	113.3 (17)
C6A—C5A—H5A	108.0	C6B—C5B—H5B	107.3
O2A—C6A—C5A	110.9 (12)	C12B—C11B—H11B	107.2
O2A—C6A—C1A	107.5 (17)	C12B—C11B—C13B	108.5 (19)
O2A—C6A—C7A	105.2 (18)	C12B—C11B—C7B	109.6 (18)
C1A—C6A—C5A	109.8 (16)	C13B—C11B—H11B	107.2
C7A—C6A—C5A	110.8 (19)	C13B—C11B—C7B	116.9 (17)
C7A—C6A—C1A	112.6 (14)	C7B—C11B—H11B	107.2
C6A—C1A—H1A	107.1	O2B—C6B—C5B	112.4 (13)
C6A—C1A—C2A	115.0 (17)	O2B—C6B—C1B	103.6 (16)
C6A—C1A—C10A	110.9 (18)	O2B—C6B—C7B	103.8 (17)
C2A—C1A—H1A	107.1	C5B—C6B—C1B	112.0 (19)
C2A—C1A—C10A	109 (2)	C5B—C6B—C7B	112.0 (19)
C10A—C1A—H1A	107.1	C1B—C6B—C7B	112.6 (14)
C1A—C2A—H2AA	108.3	C6B—C1B—H1B	107.7
C1A—C2A—H2AB	108.3	C6B—C1B—C10B	111.8 (17)
C1A—C2A—C3A	116 (2)	C2B—C1B—C6B	112.0 (15)
H2AA—C2A—H2AB	107.4	C2B—C1B—H1B	107.7
C3A—C2A—H2AA	108.3	C2B—C1B—C10B	109.8 (18)
C3A—C2A—H2AB	108.3	C10B—C1B—H1B	107.7
C4A—C3A—C2A	118 (2)	C1B—C2B—H2BA	108.0
C4A—C3A—H3AA	107.9	C1B—C2B—H2BB	108.0
C4A—C3A—H3AB	107.9	C1B—C2B—C3B	117 (2)
C2A—C3A—H3AA	107.9	H2BA—C2B—H2BB	107.2
C2A—C3A—H3AB	107.9	C3B—C2B—H2BA	108.0
H3AA—C3A—H3AB	107.2	C3B—C2B—H2BB	108.0
O4A—C12A—C11A	117 (2)	C4B—C3B—C2B	115.1 (19)
O5A—C12A—O4A	120.1 (19)	C4B—C3B—H3BA	108.5
O5A—C12A—C11A	123 (2)	C4B—C3B—H3BB	108.5
C12A—C11A—H11A	105.9	C2B—C3B—H3BA	108.5
C12A—C11A—C13A	110 (2)	C2B—C3B—H3BB	108.5
C12A—C11A—C7A	113 (2)	H3BA—C3B—H3BB	107.5
C13A—C11A—H11A	105.9	O4B—C12B—C11B	119 (2)
C13A—C11A—C7A	114.7 (18)	O5B—C12B—O4B	120.0 (18)
C7A—C11A—H11A	105.9	O5B—C12B—C11B	121 (2)
C11A—C13A—H13A	109.5	C11B—C13B—H13D	109.5
C11A—C13A—H13B	109.5	C11B—C13B—H13E	109.5
C11A—C13A—H13C	109.5	C11B—C13B—H13F	109.5
H13A—C13A—H13B	109.5	H13D—C13B—H13E	109.5
H13A—C13A—H13C	109.5	H13D—C13B—H13F	109.5
H13B—C13A—H13C	109.5	H13E—C13B—H13F	109.5
C6A—C7A—C11A	109.8 (16)	C11B—C7B—H7B	107.2
C6A—C7A—H7A	108.2	C11B—C7B—C8B	114.1 (17)
C6A—C7A—C8A	111.1 (19)	C6B—C7B—C11B	109.8 (16)
C11A—C7A—H7A	108.2	C6B—C7B—H7B	107.2
C8A—C7A—C11A	111 (2)	C6B—C7B—C8B	111.0 (18)
C8A—C7A—H7A	108.2	C8B—C7B—H7B	107.2
C7A—C8A—H8AA	109.5	C7B—C8B—H8BA	110.0
C7A—C8A—H8AB	109.5	C7B—C8B—H8BB	110.0
C7A—C8A—C9A	110.8 (19)	H8BA—C8B—H8BB	108.4
H8AA—C8A—H8AB	108.1	C9B—C8B—C7B	108.4 (18)
C9A—C8A—H8AA	109.5	C9B—C8B—H8BA	110.0
C9A—C8A—H8AB	109.5	C9B—C8B—H8BB	110.0
C8A—C9A—H9AA	108.7	C8B—C9B—H9BA	108.1
C8A—C9A—H9AB	108.7	C8B—C9B—H9BB	108.1
H9AA—C9A—H9AB	107.6	C8B—C9B—C10B	116.6 (17)
C10A—C9A—C8A	114.0 (17)	H9BA—C9B—H9BB	107.3
C10A—C9A—H9AA	108.7	C10B—C9B—H9BA	108.1
C10A—C9A—H9AB	108.7	C10B—C9B—H9BB	108.1
C1A—C10A—H10A	107.5	C1B—C10B—H10B	108.2
C9A—C10A—C1A	111 (2)	C9B—C10B—C1B	108.7 (18)
C9A—C10A—H10A	107.5	C9B—C10B—H10B	108.2
C14A—C10A—C1A	112 (2)	C14B—C10B—C1B	112.6 (19)
C14A—C10A—C9A	111.3 (17)	C14B—C10B—C9B	110.9 (16)
C14A—C10A—H10A	107.5	C14B—C10B—H10B	108.2
C10A—C14A—H14A	109.5	C10B—C14B—H14D	109.5
C10A—C14A—H14B	109.5	C10B—C14B—H14E	109.5
C10A—C14A—H14C	109.5	C10B—C14B—H14F	109.5
H14A—C14A—H14B	109.5	H14D—C14B—H14E	109.5
H14A—C14A—H14C	109.5	H14D—C14B—H14F	109.5
H14B—C14A—H14C	109.5	H14E—C14B—H14F	109.5

O3A—C4A—C3A—C2A	28 (2)	O3B—C4B—C3B—C2B	28 (2)
O3A—C5A—C6A—O2A	−53 (3)	O3B—C5B—C6B—O2B	−49 (3)
O3A—C5A—C6A—C1A	66.0 (19)	O3B—C5B—C6B—C1B	67 (2)
O3A—C5A—C6A—C7A	−169.0 (15)	O3B—C5B—C6B—C7B	−165.4 (15)
O1A—O2A—C6A—C5A	12 (3)	O1B—O2B—C6B—C5B	8 (3)
O1A—O2A—C6A—C1A	−108.5 (19)	O1B—O2B—C6B—C1B	−113 (2)
O1A—O2A—C6A—C7A	131.4 (18)	O1B—O2B—C6B—C7B	128.8 (19)
O1A—C4A—C3A—C2A	−92 (2)	O1B—C4B—C3B—C2B	−93 (2)
O2A—O1A—C4A—O3A	−73.6 (17)	O2B—O1B—C4B—O3B	−76.7 (17)
O2A—O1A—C4A—C15A	172.7 (16)	O2B—O1B—C4B—C15B	169.5 (17)
O2A—O1A—C4A—C3A	45.5 (17)	O2B—O1B—C4B—C3B	44.3 (18)
O2A—C6A—C1A—C2A	64.2 (19)	O2B—C6B—C1B—C2B	68.8 (19)
O2A—C6A—C1A—C10A	−171 (2)	O2B—C6B—C1B—C10B	−167.5 (17)
O2A—C6A—C7A—C11A	−63.8 (18)	O2B—C6B—C7B—C11B	−64.5 (16)
O2A—C6A—C7A—C8A	172.9 (17)	O2B—C6B—C7B—C8B	168.5 (15)
O4A—C5A—C6A—O2A	69 (3)	O4B—C5B—C6B—O2B	74 (3)
O4A—C5A—C6A—C1A	−172.8 (14)	O4B—C5B—C6B—C1B	−169.7 (14)
O4A—C5A—C6A—C7A	−47.7 (18)	O4B—C5B—C6B—C7B	−42.2 (19)
O4A—C12A—C11A—C13A	165.6 (18)	C15B—C4B—C3B—C2B	148 (2)
O4A—C12A—C11A—C7A	35 (3)	C4B—O3B—C5B—O4B	−99.2 (16)
O5A—C12A—C11A—C13A	−16 (3)	C4B—O3B—C5B—C6B	27 (2)
O5A—C12A—C11A—C7A	−146 (2)	C4B—O1B—O2B—C6B	51 (2)
C15A—C4A—C3A—C2A	145 (2)	C5B—O3B—C4B—O1B	34 (2)
C4A—O3A—C5A—O4A	−95.2 (17)	C5B—O3B—C4B—C15B	146 (2)
C4A—O3A—C5A—C6A	30 (2)	C5B—O3B—C4B—C3B	−89.1 (19)
C4A—O1A—O2A—C6A	48 (2)	C5B—O4B—C12B—O5B	155.4 (16)
C5A—O3A—C4A—O1A	31 (2)	C5B—O4B—C12B—C11B	−29 (3)
C5A—O3A—C4A—C15A	145.7 (19)	C5B—C6B—C1B—C2B	−52.5 (19)
C5A—O3A—C4A—C3A	−91.2 (19)	C5B—C6B—C1B—C10B	71 (2)
C5A—O4A—C12A—O5A	152.9 (18)	C5B—C6B—C7B—C11B	56.9 (18)
C5A—O4A—C12A—C11A	−29 (3)	C5B—C6B—C7B—C8B	−70.0 (18)
C5A—C6A—C1A—C2A	−57 (2)	C11B—C7B—C8B—C9B	−178.7 (16)
C5A—C6A—C1A—C10A	68 (2)	C6B—C1B—C2B—C3B	−35 (2)
C5A—C6A—C7A—C11A	56.1 (19)	C6B—C1B—C10B—C9B	52 (2)
C5A—C6A—C7A—C8A	−67.2 (18)	C6B—C1B—C10B—C14B	174.9 (17)
C6A—C1A—C2A—C3A	−27 (2)	C6B—C7B—C8B—C9B	−54 (2)
C6A—C1A—C10A—C9A	53 (2)	C1B—C6B—C7B—C11B	−175.9 (13)
C6A—C1A—C10A—C14A	178.0 (17)	C1B—C6B—C7B—C8B	57.1 (18)
C6A—C7A—C8A—C9A	−54 (2)	C1B—C2B—C3B—C4B	54 (2)
C1A—C6A—C7A—C11A	179.5 (12)	C2B—C1B—C10B—C9B	176.5 (15)
C1A—C6A—C7A—C8A	56 (2)	C2B—C1B—C10B—C14B	−60 (2)
C1A—C2A—C3A—C4A	49 (2)	C12B—O4B—C5B—O3B	155.1 (15)
C2A—C1A—C10A—C9A	−179.2 (17)	C12B—O4B—C5B—C6B	28 (2)
C2A—C1A—C10A—C14A	−54 (2)	C12B—C11B—C7B—C6B	−54 (2)
C12A—O4A—C5A—O3A	159.6 (15)	C12B—C11B—C7B—C8B	71 (2)
C12A—O4A—C5A—C6A	35 (2)	C13B—C11B—C12B—O4B	169.4 (17)
C12A—C11A—C7A—C6A	−50 (2)	C13B—C11B—C12B—O5B	−15 (2)
C12A—C11A—C7A—C8A	74 (2)	C13B—C11B—C7B—C6B	−178.1 (16)
C11A—C7A—C8A—C9A	−176.1 (17)	C13B—C11B—C7B—C8B	−53 (2)
C13A—C11A—C7A—C6A	−177.6 (16)	C7B—C11B—C12B—O4B	41 (2)
C13A—C11A—C7A—C8A	−54 (3)	C7B—C11B—C12B—O5B	−143.3 (19)
C7A—C6A—C1A—C2A	179.5 (15)	C7B—C6B—C1B—C2B	−179.7 (13)
C7A—C6A—C1A—C10A	−56 (2)	C7B—C6B—C1B—C10B	−56 (2)
C7A—C8A—C9A—C10A	53 (2)	C7B—C8B—C9B—C10B	55 (2)
C8A—C9A—C10A—C1A	−53 (2)	C8B—C9B—C10B—C1B	−54 (2)
C8A—C9A—C10A—C14A	−178.6 (14)	C8B—C9B—C10B—C14B	−178.0 (14)
C10A—C1A—C2A—C3A	−152.9 (17)	C10B—C1B—C2B—C3B	−159.6 (17)

Acknowledgements

We acknowledge the support of the Engineering and Physical Sciences Research Council (EPSRC) and GlaxoSmithKline, who funded this work through and iCASE studentship (BF). We also acknowledge Diamond Light Source for provision of beamtime under allocation CY32131. We would like to thank Professor Katharina Edkins for comments on the manuscript.

Conflict of interest

There are no conflicts of interest

Data availability

The authors would like to acknowledge that all data underpinning this publication are openly available from Zenodo repository(doi: https://doi.org/10.5281/zenodo.19714537).

Funding information

The following funding is acknowledged: Engineering and Physical Sciences Research Council (studentship No. 220018 to Banaz Fetah); GlaxoSmithKline (studentship No. 220018); Engineering and Physical Sciences Research Council (grant No. EP/N015401/1 to Iain Oswald); Higher Education Funding Council for England (grant No. HH13054).

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

Form (III) of artemisinin: discovery and crystallographic characterization of a new high-pressure polymorph

1. Introduction

2. Materials and methods

2.1. Materials

2.2. Method of preparation for recrystallization

2.3. High-pressure DAC

2.3.1. High-pressure annealing

2.4. Sapphire capillary cell (SCC)

2.5. Single-crystal X-ray diffraction (SC-XRD)

2.6. Structural analysis

3. Results and discussion

3.1. Form (I)

3.1.1. Effect of pressure on form (I)

3.2. Form (II)

3.2.1. Effect of pressure on ART form (II)

3.3. Compression of form (III)

3.4. Comparison of polymorphic forms of ART

4. Conclusion

Supporting information

Acknowledgements

Conflict of interest

Data availability

Funding information

References

research papers