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_7251049
_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         '2(C19 H28 O8), C6 H12 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
_atom_sites_solution_primary     dual
_audit_creation_date             2025-09-09
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424ae for OlexSys, GUI svn.r7311)
;
_audit_update_record
;
2025-10-07 deposited with the CCDC.	2025-10-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.644(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.3355(2)
_cell_length_b                   10.1548(2)
_cell_length_c                   21.6741(3)
_cell_measurement_reflns_used    19686
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      76.9990
_cell_measurement_theta_min      4.1750
_cell_volume                     2219.64(7)
_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      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.970
_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    -81.00   3.00   0.50    1.31    --  -47.29 104.00-144.00  168
  2  \w     18.00  58.00   0.50    1.31    --   47.29-104.00 113.00   80
  3  \w   -155.00 -89.00   0.50    5.23    --  -91.75-104.00 113.00  132
  4  \w    -73.00 -47.00   0.50    5.23    --  -91.75 104.00-144.00   52
  5  \w    109.00 175.00   0.50    5.23    --  106.64 104.00-144.00  132
  6  \w     77.00 105.00   0.50    5.23    --  106.64-104.00 113.00   56
  7  \w    -38.00  24.00   0.50    1.31    --  -47.29  37.00 120.00  124
  8  \w    -24.00  27.00   0.50    1.31    --  -47.29  19.00-150.00  102
  9  \w    -26.00  10.00   0.50    1.31    --  -47.29  19.00-180.00   72
 10  \w    -53.00 -13.00   0.50    1.31    --  -47.29 125.00   0.00   80
 11  \w     -7.00  27.00   0.50    1.31    --  -47.29  19.00  30.00   68
 12  \w     31.00  62.00   0.50    1.31    --   47.29 -57.00-150.00   62
 13  \w    -27.00  18.00   0.50    1.31    --   47.29 -19.00-120.00   90
 14  \w    -16.00  26.00   0.50    1.31    --   47.29 -19.00-180.00   84
 15  \w    -24.00   2.00   0.50    1.31    --   47.29 -19.00  90.00   52
 16  \w    -49.00 -21.00   0.50    5.23    --  -91.75  45.00-120.00   56
 17  \w    -71.00 -22.00   0.50    5.23    --  -91.75  61.00-180.00   98
 18  \w   -163.00-103.00   0.50    5.23    --  -91.75 -94.00-180.00  120
 19  \w   -163.00-132.00   0.50    5.23    --  -91.75 -61.00 -30.00   62
 20  \w    -51.00 -20.00   0.50    5.23    --  -91.75  45.00 -60.00   62
 21  \w    -51.00 -25.00   0.50    5.23    --  -91.75  45.00 150.00   52
 22  \w   -163.00-106.00   0.50    5.23    --  -91.75 -94.00  60.00  114
 23  \w    -57.00 -26.00   0.50    5.23    --  -91.75 125.00   0.00   62
 24  \w   -159.00-131.00   0.50    5.23    --  -91.75 -61.00 150.00   56
 25  \w    -51.00 -26.00   0.50    5.23    --  -91.75  45.00 -30.00   50
 26  \w    -51.00 -22.00   0.50    5.23    --  -91.75  45.00  60.00   58
 27  \w   -153.00-106.00   0.50    5.23    --  -91.75 -77.00  60.00   94
 28  \w   -149.00-123.00   0.50    5.23    --  -91.75 -77.00 -60.00   52
 29  \w   -128.00 -99.00   0.50    5.23    --  -91.75 -61.00 -30.00   58
 30  \w   -163.00 -99.00   0.50    5.23    --  -91.75 -61.00   0.00  128
 31  \w    -47.00 -20.00   0.50    5.23    --  -91.75  45.00  30.00   54
 32  \w     47.00 110.00   0.50    5.23    --  106.64-125.00 -90.00  126
 33  \w     42.00  67.00   0.50    5.23    --  106.64 -61.00-120.00   50
 34  \w     48.00  74.00   0.50    5.23    --  106.64 -94.00 -60.00   52
 35  \w     41.00  99.00   0.50    5.23    --  106.64-125.00  30.00  116
 36  \w     79.00 104.00   0.50    5.23    --  106.64 -94.00 150.00   50
 37  \w     35.00  61.00   0.50    5.23    --  106.64 -94.00 150.00   52
 38  \w     37.00  62.00   0.50    5.23    --  106.64 -61.00 -60.00   50
 39  \w     65.00 111.00   0.50    5.23    --  106.64-125.00  60.00   92
 40  \w     57.00 111.00   0.50    5.23    --  106.64-125.00  90.00  108
 41  \w    136.00 162.00   0.50    5.23    --  106.64 125.00 -60.00   52
 42  \w    106.00 132.00   0.50    5.23    --  106.64 125.00 -60.00   52
 43  \w     82.00 108.00   0.50    5.23    --  106.64-107.00 161.75   52
 44  \w     78.00 104.00   0.50    5.23    --  106.64 -94.00-120.00   52
 45  \w     54.00  79.00   0.50    5.23    --  106.64-107.00 161.75   50
 46  \w     52.00 102.00   0.50    5.23    --  106.64 -94.00 -90.00  100
 47  \w     49.00  74.00   0.50    5.23    --  106.64 -94.00-120.00   50
 48  \w     35.00  60.00   0.50    5.23    --  106.64 -61.00 150.00   50
 49  \w    138.00 178.00   0.50    5.23    --  106.64  61.00 -90.00   80
 50  \w     99.00 124.00   0.50    5.23    --  106.64  61.00 -90.00   50
 51  \w     39.00 108.00   0.50    5.23    --  106.64-125.00 120.00  138
 52  \w     79.00 105.00   0.50    5.23    --  106.64 -94.00 -60.00   52
;
_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      -0.0038105000
_diffrn_orient_matrix_UB_12      -0.1410753000
_diffrn_orient_matrix_UB_13      0.0257442000
_diffrn_orient_matrix_UB_21      -0.1181596000
_diffrn_orient_matrix_UB_22      0.0380903000
_diffrn_orient_matrix_UB_23      0.0289788000
_diffrn_orient_matrix_UB_31      -0.0966374000
_diffrn_orient_matrix_UB_32      -0.0409984000
_diffrn_orient_matrix_UB_33      -0.0616861000
_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  0.0488
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            31749
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.338
_diffrn_reflns_theta_min         4.181
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.830
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.632
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.84a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_description       needle
_exptl_crystal_F_000             948
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 3451 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.12(7)
_refine_ls_extinction_coef       0.0025(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     568
_refine_ls_number_reflns         8877
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0377
_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^)+(0.0512P)^2^+0.2862P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.0980
_reflns_Friedel_coverage         0.833
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.908
_reflns_number_gt                8181
_reflns_number_total             8877
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00279f2.cif
_cod_data_source_block           shape_based
_cod_depositor_comments
'Adding full bibliography for 7251047--7251052.cif.'
_cod_database_code               7251049
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C44 H66 N2 O16'
_chemical_oxdiff_usercomment     arts-ure-etoh
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.813
_diffrn_oxdiff_ac3_digest_hkl    0199a88f0e7c2154d2d000fcd7f4aff194e232
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(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(H5C), C6(H6), C8A(H8C), C9(H9), C10(H10), C12(H12), C5AB(H5BX), C6B(H6B),
 C8AB(H8AB), C9B(H9B), C10B(H10B), C12B(H12B)
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), C3D(H3DA,H3DB), C4D(H4DA,H4DB), C5D(H5DA,H5DB), C6D(H6DA,H6DB),
 C7D(H7DA,H7DB), C8D(H8DA,H8DB), C4B(H4BA,H4BB), C5B(H5BA,H5BB), C7B(H7BA,H7BB),
  C8B(H8BA,H8BB), C17B(H17C,H17D), C18B(H18C,H18D)
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), O21B(H21B)
;
_shelx_res_checksum              14642
_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 1.591
_oxdiff_exptl_absorpt_empirical_full_min 0.717