Mechanochemical synthesis insights and solid-state characterization of quininium aspirinate, a glass-forming drug‒drug salt
Harris, Nehemiah; Benedict, Jubilee; Dickie, Diane A.; Pagola, Silvina; Acta Crystallographica Section C 77 (2021) –; doi:10.1107/S2053229621008275

data_2022429
_publ_section_title
;
 Mechanochemical synthesis insights and solid-state characterization of
 quininium aspirinate, a glass-forming drug--drug salt
;
_journal_coeditor_code           EP3016
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229621008275
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C20 H25 N2 O2 +, C9 H7 O4 -'
_chemical_formula_moiety         'C20 H25 N2 O2 +, C9 H7 O4 -'
_chemical_formula_sum            'C29 H32 N2 O6'
_chemical_formula_weight         504.56
_chemical_name_common            'Quininium aspirinate'
_chemical_name_systematic
'(<i>R</i>)-[(2<i>S</i>,4<i>S</i>,5<i>R</i>)-5-Ethenyl-1-azoniabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol 2-acetoxybenzoate'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6256(12)
_cell_length_b                   9.6680(13)
_cell_length_c                   30.557(4)
_cell_measurement_reflns_used    8326
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      24.6890
_cell_measurement_theta_min      2.4535
_cell_volume                     2548.2(6)
_computing_cell_refinement
;
SAINT (Bruker, 2017)
;
_computing_data_collection
;
APEX3 (Bruker, 2017)
;
_computing_data_reduction
;
SAINT (Bruker, 2017)
;
_computing_structure_refinement
;
SHELXL2017 (Sheldrick, 2015b) and
OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0673
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            45099
_diffrn_reflns_theta_full        26.39
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         2.21
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2017)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.3152
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.228
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.175
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.193
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 1588 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.2(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         5223
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0399
_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^)+(0.0287P)^2^+0.6236P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0739
_refine_ls_wR_factor_ref         0.0798
_reflns_number_gt                4290
_reflns_number_total             5223
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ep3016sup1.cif
_cod_data_source_block           I
_cod_database_code               2022429
_shelx_hkl_checksum              42294
_shelx_res_checksum              70465
_cod_database_fobs_code 2022429