Novel multicomponent crystal forms of artesunate
Madu, Shadrack J.; Wang, Ke; Fábián, László; Li, Mingzhong; CrystEngComm 27 (2025) 7146–7169; doi:10.1039/D5CE00279F

data_7251050
_publ_section_title
;
 Novel multicomponent crystal forms of artesunate
;
_journal_issue                   44
_journal_name_full               CrystEngComm
_journal_page_first              7146
_journal_page_last               7169
_journal_paper_doi               10.1039/D5CE00279F
_journal_volume                  27
_journal_year                    2025
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C19 H28 O8, C19 H27 O8, C6 H13 N2'
_chemical_formula_sum            'C44 H68 N2 O16'
_chemical_formula_weight         881.00
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-09-04
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec141 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2025-02-26 deposited with the CCDC.	2025-10-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.743(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.0046(11)
_cell_length_b                   8.5912(8)
_cell_length_c                   23.6155(18)
_cell_measurement_reflns_used    6045
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      66.9450
_cell_measurement_theta_min      3.7230
_cell_volume                     2206.7(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -27.00  21.00   0.50   10.00    --  -49.31  22.00  65.00   96
  2  \w   -122.00 -44.00   0.50   10.00    --  -49.31 -22.00-100.00  156
  3  \w     50.00 117.00   0.50   10.00    --   49.31  22.00  65.00  134
  4  \w     -7.00  20.00   0.50   10.00    --   49.31 -22.00-100.00   54
  5  \w   -142.00 -89.00   0.50   10.00    --  -90.00 -22.00-100.00  106
  6  \w    102.00 156.00   0.50   10.00    --  106.00  22.00  65.00  108
  7  \w    -24.00  14.00   0.50   10.00    --  -49.31  19.00-150.00   76
  8  \w   -120.00 -95.00   0.50   10.00    --  -49.31 -57.00  90.00   50
  9  \w    -62.00 -23.00   0.50   10.00    --  -90.00  57.00  60.00   78
 10  \w   -142.00-102.00   0.50   10.00    --  -90.00 -99.00   0.00   80
 11  \w   -146.00 -94.00   0.50   10.00    --  -90.00 -57.00   0.00  104
 12  \w    -45.00 -19.00   0.50   10.00    --  -90.00  57.00-150.00   52
 13  \w    -79.00 -54.00   0.50   10.00    --  -90.00 125.00-180.00   50
 14  \w    -80.00 -54.00   0.50   10.00    --  -90.00 125.00 120.00   52
 15  \w    -56.00 -21.00   0.50   10.00    --  -90.00  57.00 -90.00   70
 16  \w     38.00  65.00   0.50   10.00    --  106.00 -57.00-180.00   54
 17  \w     40.00  66.00   0.50   10.00    --  106.00 -57.00  90.00   52
 18  \w     34.00  65.00   0.50   10.00    --  106.00 -57.00 -30.00   62
 19  \w     61.00 101.00   0.50   10.00    --  106.00 -99.00-180.00   80
 20  \w     69.00 112.00   0.50   10.00    --  106.00-125.00 150.00   86
 21  \w     34.00  60.00   0.50   10.00    --  106.00 -57.00 150.00   52
 22  \w     40.00  66.00   0.50   10.00    --  106.00 -57.00 -90.00   52
 23  \w     34.00  65.00   0.50   10.00    --  106.00 -57.00  60.00   62
 24  \w     34.00  59.00   0.50   10.00    --  106.00 -57.00   0.00   50
 25  \w     38.00  65.00   0.50   10.00    --  106.00 -57.00 120.00   54
 26  \w     36.00  63.00   0.50   10.00    --  106.00 -57.00 -60.00   54
 27  \w     37.00  65.00   0.50   10.00    --  106.00-125.00 150.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1340423000
_diffrn_orient_matrix_UB_12      0.0493145000
_diffrn_orient_matrix_UB_13      -0.0011069000
_diffrn_orient_matrix_UB_21      0.0271410000
_diffrn_orient_matrix_UB_22      -0.0151202000
_diffrn_orient_matrix_UB_23      0.0656441000
_diffrn_orient_matrix_UB_31      0.0359283000
_diffrn_orient_matrix_UB_32      -0.1722328000
_diffrn_orient_matrix_UB_33      -0.0060876000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0738
_diffrn_reflns_av_unetI/netI     0.0713
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            15522
_diffrn_reflns_point_group_measured_fraction_full 0.731
_diffrn_reflns_point_group_measured_fraction_max 0.731
_diffrn_reflns_theta_full        67.055
_diffrn_reflns_theta_max         67.055
_diffrn_reflns_theta_min         3.788
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.835
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.84a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       plate
_exptl_crystal_F_000             948
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.662
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details
;
 Flack x determined using 1172 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     566
_refine_ls_number_reflns         5760
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0800
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1771P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2265
_refine_ls_wR_factor_ref         0.2489
_reflns_Friedel_coverage         0.370
_reflns_Friedel_fraction_full    0.426
_reflns_Friedel_fraction_max     0.426
_reflns_number_gt                4224
_reflns_number_total             5760
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00279f2.cif
_cod_data_source_block           ATS2-DABCO-2
_cod_depositor_comments
'Adding full bibliography for 7251047--7251052.cif.'
_cod_database_code               7251050
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C44 H68 N2 O16'
_chemical_oxdiff_usercomment     'bis(artesunate) dabco salt cocrystal'
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.885
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C5A(H5AA), C6(H6), C8A(H8AA), C9(H9), C10(H10), C12(H12), C5AB(H5AB),
 C6B(H6B), C8AB(H8AB), C9B(H9B), C10B(H10B), C12B(H12B), N1D(H1D)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B), C17(H17A,H17B), C18(H18A,
 H18B), C4B(H4BA,H4BB), C5B(H5BA,H5BB), C7B(H7BA,H7BB), C8B(H8BA,H8BB),
 C17B(H17C,H17D), C18B(H18C,H18D), C3D(H3DA,H3DB), C4D(H4DA,H4DB), C5D(H5DA,
 H5DB), C6D(H6DA,H6DB), C7D(H7DA,H7DB), C8D(H8DA,H8DB)
2.c Idealised Me refined as rotating group:
 C3M(H3MA,H3MB,H3MC), C6M(H6MA,H6MB,H6MC), C9M(H9MA,H9MB,H9MC), C3MB(H3MD,H3ME,
 H3MF), C6MB(H6MD,H6ME,H6MF), C9MB(H9MD,H9ME,H9MF)
2.d Idealised tetrahedral OH refined as rotating group:
 O21(H21)
;
_shelx_res_checksum              27313
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.980
_oxdiff_exptl_absorpt_empirical_full_min 0.474