Artemisinin–acetylenedicarboxylic acid cocrystal: screening, structure determination, and physicochemical property characterisation
Makadia, Jay; Madu, Shadrack J.; Arroo, Randolph; Seaton, Colin C.; Li, Mingzhong; CrystEngComm 24 (2022) 1056–1067; doi:10.1039/D1CE01400E

data_7244114
_publ_section_title
;
 Artemisinin--acetylenedicarboxylic acid cocrystal: screening, structure
 determination, and physicochemical property characterisation
;
_journal_issue                   5
_journal_name_full               CrystEngComm
_journal_page_first              1056
_journal_page_last               1067
_journal_paper_doi               10.1039/D1CE01400E
_journal_volume                  24
_journal_year                    2022
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C15 H22 O5, 0.5(C4 H2 O4)'
_chemical_formula_sum            'C17 H23 O7'
_chemical_formula_weight         339.35
_chemical_name_common
;
artesiminin hemikis(acetylenedicarboxylic acid)
;
_chemical_name_systematic
'Octahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin-10(3H)-one hemikis(but-2-ynedioic acid)'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-10-12 deposited with the CCDC.	2021-12-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5089(4)
_cell_length_b                   24.0830(11)
_cell_length_c                   6.4952(3)
_cell_measurement_reflns_used    7627
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      33.39
_cell_measurement_theta_min      2.54
_cell_volume                     1643.84(12)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      149.99
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.761
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.761
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            17651
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.721
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.253
_diffrn_reflns_theta_min         2.114
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       block
_exptl_crystal_F_000             724
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chloroform/Methanol (90%:10%)'
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 2017 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         5737
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0353
_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^)+(0.0603P)^2^+0.0505P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0922
_reflns_Friedel_coverage         0.681
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.669
_reflns_number_gt                5191
_reflns_number_total             5737
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce01400e2.cif
_cod_data_source_block           ml_art
_cod_depositor_comments          'Adding full bibliography for 7244114.cif.'
_cod_database_code               7244114
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.929
_olex2_refinement_description
;
;
_shelx_res_checksum              10447
_shelx_hkl_checksum              86352
_olex2_submission_special_instructions 'No special instructions were received'