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_7251051
_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, C12 H8 N2'
_chemical_formula_sum            'C31 H36 N2 O8'
_chemical_formula_weight         564.62
_chemical_name_common            'artesunate 1,10-phenanthroline'
_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             2023-09-05
_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                 118.766(3)
_cell_angle_gamma                90
_cell_formula_units_Z            6
_cell_length_a                   9.57054(18)
_cell_length_b                   51.5305(6)
_cell_length_c                   9.8305(2)
_cell_measurement_reflns_used    16423
_cell_measurement_temperature    99.98(11)
_cell_measurement_theta_max      76.8270
_cell_measurement_theta_min      3.4210
_cell_volume                     4249.85(18)
_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  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.878
_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   -118.00 -72.00   0.50    0.82    --  -47.29-129.00 -22.00   92
  2  \w    -32.00  -4.00   0.50    0.82    --  -47.29  31.00-170.00   56
  3  \w   -165.00-122.00   0.50    3.30    --  -91.75 -31.00  29.00   86
  4  \w    -57.00 -21.00   0.50    3.30    --  -91.75  92.00 -20.00   72
  5  \w     51.00 118.00   0.50    3.30    --  106.64-140.00 164.00  134
  6  \w    -17.00   9.00   0.50    0.82    --  -47.29  19.00 -90.00   52
  7  \w   -118.00 -63.00   0.50    0.82    --  -47.29-140.00 164.00  110
  8  \w    -18.00  18.00   0.50    0.82    --   47.29 -19.00 -30.00   72
  9  \w    -51.00 -26.00   0.50    3.30    --  -91.75  45.00-120.00   50
 10  \w    -46.00 -20.00   0.50    3.30    --  -91.75  45.00 -30.00   52
 11  \w    -62.00 -36.00   0.50    3.30    --  -91.75  61.00  90.00   52
 12  \w   -160.00-106.00   0.50    3.30    --  -91.75 -77.00 -90.00  108
 13  \w    -71.00 -20.00   0.50    3.30    --  -91.75  61.00 -90.00  102
 14  \w    -50.00 -23.00   0.50    3.30    --  -91.75  45.00 -90.00   54
 15  \w    -68.00 -30.00   0.50    3.30    --  -91.75  61.00   0.00   76
 16  \w    144.00 171.00   0.50    3.30    --  106.64  77.00-150.00   54
 17  \w    107.00 132.00   0.50    3.30    --  106.64  77.00-150.00   50
 18  \w     39.00  64.00   0.50    3.30    --  106.64 -61.00   0.00   50
 19  \w     61.00  99.00   0.50    3.30    --  106.64 -77.00 -90.00   76
 20  \w     39.00  64.00   0.50    3.30    --  106.64 -61.00 120.00   50
 21  \w     44.00  91.00   0.50    3.30    --  106.64 -77.00-120.00   94
;
_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      -0.1373632000
_diffrn_orient_matrix_UB_12      -0.0039223000
_diffrn_orient_matrix_UB_13      0.0375864000
_diffrn_orient_matrix_UB_21      -0.1184114000
_diffrn_orient_matrix_UB_22      0.0111862000
_diffrn_orient_matrix_UB_23      -0.1598890000
_diffrn_orient_matrix_UB_31      -0.0286365000
_diffrn_orient_matrix_UB_32      -0.0274509000
_diffrn_orient_matrix_UB_33      -0.0705460000
_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     0.0449
_diffrn_reflns_Laue_measured_fraction_full 0.953
_diffrn_reflns_Laue_measured_fraction_max 0.878
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -64
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            23260
_diffrn_reflns_point_group_measured_fraction_full 0.655
_diffrn_reflns_point_group_measured_fraction_max 0.598
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.294
_diffrn_reflns_theta_min         3.431
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.789
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.462
_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            'clear colourless'
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1800
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 2414 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1120
_refine_ls_number_reflns         10786
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0761P)^2^+0.7331P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1220
_reflns_Friedel_coverage         0.345
_reflns_Friedel_fraction_full    0.350
_reflns_Friedel_fraction_max     0.310
_reflns_number_gt                10239
_reflns_number_total             10786
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00279f2.cif
_cod_data_source_block           ATS-PHEN
_cod_depositor_comments
'Adding full bibliography for 7251047--7251052.cif.'
_cod_original_cell_volume        4249.88(16)
_cod_database_code               7251051
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C31 H36 N2 O8'
_shelx_estimated_absorpt_t_max   0.911
_shelx_estimated_absorpt_t_min   0.815
_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(H5AA), C6(H6), C8A(H8AA), C9(H9), C10(H10), C12(H12), C5AB(H5AB),
 C6B(H6B), C8AB(H8AB), C9B(H9B), C10B(H10B), C12B(H12B), C5AD(H5AD), C6D(H6D),
 C8AD(H8AD), C9D(H9D), C10D(H10D), C12D(H12D)
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), C4D(H4DA,H4DB), C5D(H5DA,H5DB), C7D(H7DA,
 H7DB), C8D(H8DA,H8DB), C17D(H17E,H17F), C18D(H18E,H18F)
2.c Aromatic/amide H refined with riding coordinates:
 C2P(H2P), C3P(H3P), C4P(H4P), C5P(H5P), C6P(H6P), C7P(H7P), C8P(H8P),
 C9P(H9P), C2Q(H2Q), C3Q(H3Q), C4Q(H4Q), C5Q(H5Q), C6Q(H6Q), C7Q(H7Q), C8Q(H8Q),
  C9Q(H9Q), C2R(H2R), C3R(H3R), C4R(H4R), C5R(H5R), C6R(H6R), C7R(H7R),
 C8R(H8R), C9R(H9R)
2.d 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), C3MD(H3MG,H3MH,H3MI),
 C6MD(H6MG,H6MH,H6MI), C9MD(H9MG,H9MH,H9MI)
2.e Idealised tetrahedral OH refined as rotating group:
 O21(H21), O21B(H21B), O21D(H21D)
;
_shelx_res_checksum              12729
_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 1.788
_oxdiff_exptl_absorpt_empirical_full_min 0.656