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_7251052
_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 rmad
_chemical_formula_moiety         'C19 H28 O8, C H4 N2 O, C H4 O'
_chemical_formula_sum            'C21 H36 N2 O10'
_chemical_formula_weight         476.52
_chemical_name_common            'artesunate urea cocrystal methanol solvate'
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2023-08-31
_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                 93.125(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.3625(5)
_cell_length_b                   7.3357(3)
_cell_length_c                   15.0315(6)
_cell_measurement_reflns_used    3351
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.6330
_cell_measurement_theta_min      2.9430
_cell_volume                     1140.94(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_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 0.979
_diffrn_measured_fraction_theta_max 0.923
_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    -51.00 -26.00   0.50    0.11    --  -91.75  45.00-120.00   50
  2  \w    -50.00 -20.00   0.50    0.11    --  -91.75  45.00 -30.00   60
  3  \w    -50.00 -20.00   0.50    0.11    --  -91.75  45.00   0.00   60
  4  \w    -51.00 -24.00   0.50    0.11    --  -91.75  45.00  30.00   54
  5  \w    -62.00 -21.00   0.50    0.11    --  -91.75  61.00  30.00   82
  6  \w    -79.00 -43.00   0.50    0.11    --  -91.75  97.00  37.00   72
  7  \w     -2.00  25.00   0.50    0.05    --  -46.59  97.00  37.00   54
  8  \w    -59.00 -16.00   0.50    0.05    --  -46.59  97.00  37.00   86
  9  \w   -152.00 -87.00   0.50    0.11    --  -91.75 -97.00 -71.00  130
 10  \w   -163.00-121.00   0.50    0.11    --  -91.75 -77.00 -30.00   84
 11  \w    -22.00  27.00   0.50    0.05    --  -46.59  19.00-180.00   98
 12  \w    -24.00  29.00   0.50    0.05    --  -46.59  19.00 -60.00  106
 13  \w     12.00  37.00   0.50    0.05    --   46.59 -97.00 -71.00   50
 14  \w     38.00 103.00   0.50    0.11    --  106.59 -97.00 -71.00  130
 15  \w     39.00 104.00   0.50    0.11    --  106.59 -77.00 -60.00  130
 16  \w     39.00  68.00   0.50    0.11    --  106.59 -61.00-150.00   58
 17  \w    -24.00  24.00   0.50    0.05    --   46.59 -19.00  30.00   96
 18  \w    -22.00  24.00   0.50    0.05    --   46.59 -19.00 -90.00   92
 19  \w     38.00  63.00   0.50    0.11    --  106.59 -61.00  60.00   50
 20  \w     34.00  59.00   0.50    0.11    --  106.59 -61.00 120.00   50
 21  \w     35.00  70.00   0.50    0.11    --  106.59 -61.00 150.00   70
 22  \w    106.00 178.00   0.50    0.11    --  106.59  45.00 -30.00  144
 23  \w    120.00 147.00   0.50    0.11    --  106.59  97.00  37.00   54
 24  \w    102.00 127.00   0.50    0.11    --  106.59 125.00 150.00   50
 25  \w    142.00 170.00   0.50    0.11    --  106.59 125.00 150.00   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      -0.0385668000
_diffrn_orient_matrix_UB_12      0.1888163000
_diffrn_orient_matrix_UB_13      0.0345587000
_diffrn_orient_matrix_UB_21      -0.1432571000
_diffrn_orient_matrix_UB_22      -0.0573361000
_diffrn_orient_matrix_UB_23      -0.0064947000
_diffrn_orient_matrix_UB_31      0.0129490000
_diffrn_orient_matrix_UB_32      -0.0719172000
_diffrn_orient_matrix_UB_33      0.0964032000
_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  0.0384
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7091
_diffrn_reflns_point_group_measured_fraction_full 0.810
_diffrn_reflns_point_group_measured_fraction_max 0.743
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.682
_diffrn_reflns_theta_min         2.944
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.929
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 1069 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.13(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         3560
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0466
_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^)+(0.0752P)^2^+0.4122P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1258
_reflns_Friedel_coverage         0.489
_reflns_Friedel_fraction_full    0.610
_reflns_Friedel_fraction_max     0.531
_reflns_number_gt                3359
_reflns_number_total             3560
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00279f2.cif
_cod_data_source_block           ATS-URE-MEOH
_cod_depositor_comments
'Adding full bibliography for 7251047--7251052.cif.'
_cod_database_code               7251052
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 98.24
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,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(H8A), C9(H9), C10(H10), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C8(H8B,H8C), C17(H17A,H17B), C18(H18A,
 H18B)
2.c X=CH2 refined with riding coordinates:
 N1U(H1UA,H1UB), N2U(H2UA,H2UB)
2.d Idealised Me refined as rotating group:
 C3M(H3MA,H3MB,H3MC), C6M(H6MA,H6MB,H6MC), C9M(H9MA,H9MB,H9MC), C1E(H1EA,H1EB,
 H1EC)
2.e Idealised tetrahedral OH refined as rotating group:
 O21(H21), O1E(H1E)
;
_shelx_res_checksum              85792
_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 1.438
_oxdiff_exptl_absorpt_empirical_full_min 0.666