Crystal structure of a 1:1 co-crystal of quabodepistat (OPC-167832) with 2,5-dihydroxybenzoic acid using microcrystal electron diffraction
Sakamoto, Nasa; Gato, Katsuhiko; Acta Crystallographica Section E Crystallographic Communications 79 (2023) –; doi:10.1107/S2056989023006047

data_2022863
_publ_section_title
;
 Crystal structure of a 1:1 co-crystal of quabodepistat (OPC-167832) with
 2,5-dihydroxybenzoic acid using microcrystal electron diffraction
;
_journal_coeditor_code           DJ2052
_journal_issue                   10
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S2056989023006047
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C21 H20 Cl F3 N2 O4, C7 H6 O4'
_chemical_formula_moiety         'C21 H20 Cl F3 N2 O4, C7 H6 O4'
_chemical_formula_sum            'C28 H26 Cl F3 N2 O8'
_chemical_formula_weight         610.96
_chemical_name_common            quabodepistat-2,5-dihydroxybenzoicacid
_chemical_name_systematic
'5-{[(3<i>R</i>,4<i>R</i>)-1-(4-Chloro-2,6-difluorophenyl)-3,4-dihydroxypiperidin-4-yl]methoxy}-8-fluoro-3,4-dihydroquinolin-2(1<i>H</i>)-one--2,5-dihydroxybenzoic acid (1/1)'
_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
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.30(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.6(3)
_cell_length_b                   9.6(3)
_cell_length_c                   28.2(3)
_cell_measurement_reflns_used    411
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      0.8340
_cell_measurement_theta_min      0.1030
_cell_volume                     1516(10)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2022)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2022)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2022)
;
_computing_molecular_graphics
;
Olex2 1.5 (Dolomanov <i>et al.</i>,  2009)
;
_computing_publication_material
;
Olex2 1.5 (Dolomanov <i>et al.</i>,  2009)
;
_computing_structure_refinement
;
<i>SHELXL2018/3</i> (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXD  (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'HPC area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.931
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-ED'
_diffrn_measurement_method       rotation
_diffrn_radiation_type           electron
_diffrn_radiation_wavelength     0.0251
_diffrn_reflns_av_R_equivalents  0.1491
_diffrn_reflns_av_unetI/netI     0.1595
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            8548
_diffrn_reflns_theta_full        0.799
_diffrn_reflns_theta_max         0.799
_diffrn_reflns_theta_min         0.107
_diffrn_source                   'thermionic-emission electron gun'
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       'thin platelets'
_exptl_crystal_F_000             224
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.146
_refine_ls_abs_structure_details
;
 All f" are zero, so absolute structure could not be determined
;
_refine_ls_extinction_coef       37E1(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
'<i>SHELXL2018/3</i> (Sheldrick, 2015)'
;
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         4096
_refine_ls_number_restraints     537
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.2455
_refine_ls_R_factor_gt           0.1602
_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^)+(0.2805P)^2^+0.1700P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4121
_refine_ls_wR_factor_ref         0.4803
_reflns_number_gt                2030
_reflns_number_total             4096
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            dj2052sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        152E1(11)
_cod_database_code               2022863
_shelx_hkl_checksum              14713
_shelx_res_checksum              58307