Multicomponent crystals of an artemisinin derivative and cinchona alkaloids for use as antimalarial drugs
Jiang, Qi; Hirsh, David A.; Tu, Yifan; Luo, Laibin; CrystEngComm 23 (2021) 6843–6847; doi:10.1039/D1CE00974E

data_7243430
_publ_section_title
;
 Multicomponent crystals of an artemisinin derivative and cinchona
 alkaloids for use as antimalarial drugs
;
_journal_issue                   39
_journal_name_full               CrystEngComm
_journal_page_first              6843
_journal_page_last               6847
_journal_paper_doi               10.1039/D1CE00974E
_journal_volume                  23
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H27 O8, C19 H23 N2 O'
_chemical_formula_sum            'C38 H50 N2 O9'
_chemical_formula_weight         678.80
_chemical_name_systematic        AS-CND
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-04-15
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-04-15 deposited with the CCDC.	2021-08-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 127.752(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   30.0476(16)
_cell_length_b                   6.6972(3)
_cell_length_c                   21.9220(12)
_cell_measurement_reflns_used    9768
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.753
_cell_measurement_theta_min      2.549
_cell_volume                     3488.0(5)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker PHOTON II CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1276
_diffrn_reflns_av_unetI/netI     0.0591
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            62257
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        66.753
_diffrn_reflns_theta_max         66.753
_diffrn_reflns_theta_min         2.549
_diffrn_source_current           0.65
_diffrn_source_power             0.02925
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.749
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.4879
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       block
_exptl_crystal_F_000             1456
_exptl_crystal_preparation       'solvent exporation in iPrOH/Heptane'
_exptl_crystal_recrystallization_method 'solvnet diffusion'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 1928 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     454
_refine_ls_number_reflns         6129
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0692
_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^)+(0.0616P)^2^+9.3100P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1550
_refine_ls_wR_factor_ref         0.1600
_reflns_Friedel_coverage         0.821
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                5497
_reflns_number_total             6129
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00974e2.cif
_cod_data_source_block           scx20_089
_cod_depositor_comments
'Adding full bibliography for 7243430--7243431.cif.'
_cod_original_cell_volume        3488.0(4)
_cod_database_code               7243430
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.835
_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:
 C2(H2), C5(H5), C7(H7), C12(H12), C13(H13), C14(H14), N2(H2A), C29(H29),
 C30(H30), C32(H32), C36(H36)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C8(H8A,H8B), C9(H9A,H9B), C17(H17A,H17B), C18(H18A,
 H18B), C31(H31A,H31B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,H35B)
2.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C21(H21), C22(H22), C23(H23), C26(H26), C27(H27), C37(H37)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C11(H11A,H11B,H11C), C15(H15A,H15B,H15C)
2.e Idealised tetrahedral OH refined as rotating group:
 O9(H9)
;
_olex2_submission_special_instructions 'No special instructions were received'