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_7251048
_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, C H4 N2 O, C2 H3 N'
_chemical_formula_sum            'C22 H35 N3 O9'
_chemical_formula_weight         485.53
_chemical_name_common            'artesunate urea acetonitrile 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
_audit_creation_date             2025-09-17
_audit_creation_method
; 
Olex2 1.5 
(compiled 2025.07.13 svn.rb7424ae for OlexSys, GUI svn.r7314) 
;
_audit_update_record
;
2025-10-07 deposited with the CCDC.	2025-10-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.315(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.5562(3)
_cell_length_b                   7.3837(2)
_cell_length_c                   15.7892(5)
_cell_measurement_reflns_used    5829
_cell_measurement_temperature    99.99(11)
_cell_measurement_theta_max      73.2760
_cell_measurement_theta_min      4.2120
_cell_volume                     1217.73(6)
_computing_cell_refinement       'CrysAlisPro 1.171.43.144a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 42.92a 64-bit (release 29-05-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.144a (Rigaku OD, 2024)'
_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)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.921
_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    -61.00 -20.00   0.50    0.95    --  -46.79  82.00 -54.00   82 
  2  \w    -16.00  26.00   0.50    0.95    --  -46.79  82.00 -54.00   84 
  3  \w    -20.00  56.00   0.50    0.95    --   46.79 -82.00-176.00  152 
  4  \w   -148.00-122.00   0.50    3.82    --  -91.75 -82.00-176.00   52 
  5  \w    -73.00 -27.00   0.50    3.82    --  -91.75  82.00 -54.00   92 
  6  \w    118.00 158.00   0.50    3.82    --  106.64  82.00 -54.00   80 
  7  \w    -40.00  25.00   0.50    0.95    --  -46.79  37.00-150.00  130 
  8  \w    -24.00  17.00   0.50    0.95    --  -46.79  19.00 -90.00   82 
  9  \w    -11.00  14.00   0.50    0.95    --   46.79 -19.00-120.00   50 
 10  \w    -16.00  11.00   0.50    0.95    --   46.79 -19.00 -60.00   54 
 11  \w    -24.00  12.00   0.50    0.95    --   46.79 -19.00-180.00   72 
 12  \w     -1.00  77.00   0.50    0.95    --   46.79 -99.00   0.00  156 
 13  \w   -135.00-103.00   0.50    3.82    --  -91.75 -45.00  60.00   64 
 14  \w   -137.00 -79.00   0.50    3.82    --  -91.75 -45.00-150.00  116 
 15  \w   -148.00 -79.00   0.50    3.82    --  -91.75 -45.00  90.00  138 
 16  \w   -162.00-109.00   0.50    3.82    --  -91.75 -61.00  60.00  106 
 17  \w    -50.00 -23.00   0.50    3.82    --  -91.75  45.00  90.00   54 
 18  \w    -51.00 -25.00   0.50    3.82    --  -91.75  45.00-120.00   52 
 19  \w    -49.00 -24.00   0.50    3.82    --  -91.75  45.00  60.00   50 
 20  \w   -157.00 -81.00   0.50    3.82    --  -91.75 -45.00-180.00  152 
 21  \w   -107.00 -82.00   0.50    3.82    --  -91.75 -30.00-120.00   50 
 22  \w    -70.00 -41.00   0.50    3.82    --  -91.75  61.00 -90.00   58 
 23  \w   -164.00-137.00   0.50    3.82    --  -91.75 -30.00-120.00   54 
 24  \w   -162.00-120.00   0.50    3.82    --  -91.75 -61.00 -90.00   84 
 25  \w   -154.00-100.00   0.50    3.82    --  -91.75 -61.00 150.00  108 
 26  \w    -48.00 -23.00   0.50    3.82    --  -91.75  45.00 150.00   50 
 27  \w   -153.00-103.00   0.50    3.82    --  -91.75 -94.00 150.00  100 
 28  \w    -50.00 -24.00   0.50    3.82    --  -91.75  45.00 -30.00   52 
 29  \w   -162.00-104.00   0.50    3.82    --  -91.75 -61.00-150.00  116 
 30  \w   -152.00 -99.00   0.50    3.82    --  -91.75 -61.00  90.00  106 
 31  \w     38.00 109.00   0.50    3.82    --  106.64-125.00  30.00  142 
 32  \w     34.00  71.00   0.50    3.82    --  106.64 -61.00 -30.00   74 
 33  \w     37.00 111.00   0.50    3.82    --  106.64-125.00 -60.00  148 
 34  \w    105.00 172.00   0.50    3.82    --  106.64  61.00   0.00  134 
 35  \w     36.00  62.00   0.50    3.82    --  106.64 -61.00  60.00   52 
 36  \w    106.00 133.00   0.50    3.82    --  106.64  45.00-120.00   54 
 37  \w    137.00 171.00   0.50    3.82    --  106.64  45.00-120.00   68 
 38  \w     35.00 101.00   0.50    3.82    --  106.64 -82.00-176.00  132 
;
_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      -0.1267303000
_diffrn_orient_matrix_UB_12      0.0805767000
_diffrn_orient_matrix_UB_13      -0.0451546000
_diffrn_orient_matrix_UB_21      0.0156719000
_diffrn_orient_matrix_UB_22      0.1621641000
_diffrn_orient_matrix_UB_23      0.0619203000
_diffrn_orient_matrix_UB_31      0.0738331000
_diffrn_orient_matrix_UB_32      0.1035830000
_diffrn_orient_matrix_UB_33      -0.0620022000
_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  0.0708
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7863
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.433
_diffrn_reflns_theta_min         2.828
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.863
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.43.144a (Rigaku Oxford Diffraction, 2024) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.309
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.142
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
; 
 Classical Flack method preferred over Parsons because s.u. lower. 
;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         7863
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0659
_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^)+(0.0986P)^2^+0.8811P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1891
_refine_ls_wR_factor_ref         0.1972
_reflns_Friedel_coverage         0.769
_reflns_Friedel_fraction_full    0.954
_reflns_Friedel_fraction_max     0.831
_reflns_number_gt                7230
_reflns_number_total             7863
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
; 
Component 2 rotated by 2.6510\% 
around [0.94 0.20 0.26] (reciprocal) or [0.91 0.37 0.20] (direct) 
;
_cod_data_source_file            d5ce00279f2.cif
_cod_data_source_block           twin
_cod_depositor_comments
'Adding full bibliography for 7251047--7251052.cif.'
_cod_database_code               7251048
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C22 H35 N3 O9'
_olex2_refinement_description
; 
1. Twinned data refinement 
 Scales: 0.448(3) 
 0.552(3) 
2. 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 
3.a Ternary CH refined with riding coordinates: 
 C5A(H5AA), C6(H6), C8A(H8AA), C9(H9), C10(H10), C12(H12) 
3.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) 
3.c X=CH2 refined with riding coordinates: 
 N1U(H1UA,H1UB), N3U(H3UA,H3UB) 
3.d Idealised Me refined as rotating group: 
 C3M(H3MA,H3MB,H3MC), C6M(H6MA,H6MB,H6MC), C9M(H9MA,H9MB,H9MC), C1S(H1SA,H1SB, 
 H1SC) 
3.e Idealised tetrahedral OH refined as rotating group: 
 O21(H21) 
;
_shelx_res_checksum              98723
_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 1.657
_oxdiff_exptl_absorpt_empirical_full_min 0.567
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2