Crystal structures of salts of bedaquiline
Okezue, Mercy; Smith, Daniel; Zeller, Matthias; Byrn, Stephen R.; Smith, Pamela; Bogandowich-Knipp, Susan; Purcell, Dale K.; Clase, Kari L.; Acta Crystallographica Section C 76 (2020) –; doi:10.1107/S2053229620013455

data_2022268
_publ_section_title
;
 Crystal structures of salts of bedaquiline
;
_journal_coeditor_code           OV3143
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229620013455
_journal_volume                  76
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_iupac          'C32 H32 Br N2 O2 +, C7 H5 O2 -, 1.166H2 O'
_chemical_formula_moiety         'C32 H32 Br N2 O2 +, C7 H5 O2 -, 1.166(H2 O)'
_chemical_formula_sum            'C39 H39.34 Br N2 O5.17'
_chemical_formula_weight         698.70
_chemical_name_common
;
Bedaqulinium benzoate 1.166-hydrate
;
_chemical_name_systematic
'[4-(6-Bromo-2-methoxyquinolin-3-yl)-3-hydroxy-3-(naphthalen-1-yl)-4-phenylbutyl]dimethylazanium benzoate hydrate'
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 99.8450(17)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.6384(5)
_cell_length_b                   7.9259(3)
_cell_length_c                   17.5249(8)
_cell_measurement_reflns_used    9883
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.9868
_cell_measurement_theta_min      2.3592
_cell_volume                     1729.63(12)
_computing_cell_refinement
;
SAINT (Bruker, 2019)
;
_computing_data_collection
;
APEX3 (Bruker, 2019)
;
_computing_data_reduction
;
SAINT (Bruker, 2019)
;
_computing_molecular_graphics
;
Mercury (Macrae <i>et al.</i>,  2020)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015) and
shelXle (H\"ubschle <i>et al.</i>,  2011)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Bruker D8 Quest diffractometer with PhotonII charge-integrating pixel
array detector (CPAD)
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            80228
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.168
_diffrn_reflns_theta_min         2.359
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_exptl_absorpt_coefficient_mu    1.235
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6378
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS2016; Krause <i>et al.</i>,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       rod
_exptl_crystal_F_000             727
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.484
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 4051 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.006(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     445
_refine_ls_number_reflns         13080
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0318
_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^)+(0.0275P)^2^+0.0775P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0671
_refine_ls_wR_factor_ref         0.0725
_reflns_number_gt                10456
_reflns_number_total             13080
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ov3143sup1.cif
_cod_data_source_block           4a
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2022268
_shelx_estimated_absorpt_t_min   0.550
_shelx_estimated_absorpt_t_max   0.856
_shelx_hkl_checksum              54850
_shelx_res_checksum              33611
_cod_database_fobs_code 2022268