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_7243431
_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_formula_moiety         'Cl, C20 H25 N2 O2, 2(H2 O)'
_chemical_formula_sum            'C20 H29 Cl N2 O4'
_chemical_formula_weight         396.90
_chemical_name_systematic        'QN HCl 2H2O'
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 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                98.689(2)
_cell_angle_beta                 97.586(2)
_cell_angle_gamma                108.323(2)
_cell_formula_units_Z            2
_cell_length_a                   6.7848(3)
_cell_length_b                   10.6171(5)
_cell_length_c                   15.4805(8)
_cell_measurement_reflns_used    9837
_cell_measurement_temperature    100
_cell_measurement_theta_max      67.245
_cell_measurement_theta_min      2.942
_cell_volume                     1027.12(9)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            28580
_diffrn_reflns_point_group_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.245
_diffrn_reflns_theta_max         67.245
_diffrn_reflns_theta_min         2.942
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           0.65
_diffrn_source_power             0.02925
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    1.873
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.4263
_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    1.283
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_preparation       'solvent evaporation'
_exptl_crystal_recrystallization_method 'slow evaporation in aqueous solution'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.613
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.05(2)
_refine_ls_extinction_coef       0.015(5)
_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   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     533
_refine_ls_number_reflns         6948
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0804
_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^)+(0.1935P)^2^+0.2661P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2147
_refine_ls_wR_factor_ref         0.2213
_reflns_Friedel_coverage         0.949
_reflns_Friedel_fraction_full    0.923
_reflns_Friedel_fraction_max     0.923
_reflns_number_gt                6911
_reflns_number_total             6948
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00974e2.cif
_cod_data_source_block           scx21_011
_cod_depositor_comments
'Adding full bibliography for 7243430--7243431.cif.'
_cod_database_code               7243431
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.835
_shelx_estimated_absorpt_t_min   0.603
_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, All O(H,H) groups
2.a Free rotating group:
 O6(H6A), O7(H7A,H7B), O8(H8A)
2.b Ternary CH refined with riding coordinates:
 N4(H4A), N2(H2A), C31(H31), C11(H11), C18(H18), C12(H12), C34(H34), C38(H38),
 C32(H32), C14(H14)
2.c Secondary CH2 refined with riding coordinates:
 C36(H36A,H36B), C33(H33A,H33B), C16(H16A,H16B), C35(H35A,H35B), C37(H37A,
 H37B), C13(H13A,H13B), C17(H17A,H17B), C15(H15A,H15B)
2.d Aromatic/amide H refined with riding coordinates:
 C9(H9), C24(H24), C28(H28), C4(H4B), C8(H8), C29(H29), C27(H27), C7(H7),
 C23(H23), C3(H3), C39(H39), C19(H19)
2.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C21(H21A,H21B,H21C)
2.f Idealised tetrahedral OH refined as rotating group:
 O4(H4), O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'