Maleate salts of bedaquiline
Zeller, Matthias; Bogdanowich-Knipp, Susan; Smith, Pamela; Purcell, Dale K.; Okezue, Mercy; Smith, Daniel T.; Byrn, Stephen R.; Clase, Kari L.; Acta Crystallographica Section E 77 (2021) 433–445; doi:10.1107/S2056989021002991

data_2243789
_publ_section_title
;
 Maleate salts of bedaquiline
;
_journal_coeditor_code           TX2038
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              433
_journal_page_last               445
_journal_paper_doi               10.1107/S2056989021002991
_journal_volume                  77
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_iupac          'C32 H32 Br N2 O2 +, C4 H3 O4 -, 0.476H2 O'
_chemical_formula_moiety         'C32 H32 Br N2 O2 +, C4 H3 O4 -, 0.476(H2 O)'
_chemical_formula_sum            'C36 H35.96 Br N2 O6.48'
_chemical_formula_weight         680.17
_chemical_name_common
;
Bedaquilinium maleate 0.476-hydrate
;
_chemical_name_systematic
'[4-(6-bromo-2-methoxyquinolin-3-yl)-3-hydroxy-3-(naphthalen-1-yl)-4-phenylbutyl]dimethylazanium 3-carboxyprop-2-enoate 0.476-hydrate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 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                 106.3762(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.7469(5)
_cell_length_b                   13.2627(4)
_cell_length_c                   17.8602(6)
_cell_measurement_reflns_used    9805
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      79.0660
_cell_measurement_theta_min      2.5786
_cell_volume                     3578.7(2)
_computing_cell_refinement
;
SAINT (Bruker, 2020)
;
_computing_data_collection
;
APEX3 (Bruker, 2020)
;
_computing_data_reduction
;
SAINT (Bruker, 2020)
;
_computing_molecular_graphics
;
Mercury (Macrae <i>et al.</i>,  2020)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
<i>SHELXL2018/3</i> (Sheldrick, 2015b),
<i>shelXle</i>  (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 0.992
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type
;
Bruker AXS D8 Quest with PhotonIII_C14 CPAD
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15060
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.762
_diffrn_reflns_theta_min         2.578
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_source_current           '1.0 mA'
_diffrn_source_voltage           '50 kV'
_exptl_absorpt_coefficient_mu    1.942
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.6457
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause <i>et al.</i>,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_description       block
_exptl_crystal_F_000             1411
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.461
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 2633 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.019(8)
_refine_ls_extinction_coef       0.00103(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     430
_refine_ls_number_reflns         7003
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0413
_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^)+(0.0255P)^2^+3.0883P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1065
_reflns_number_gt                6474
_reflns_number_total             7003
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            tx2038sup1.cif
_cod_data_source_block           hemihydrate
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               2243789
_shelx_estimated_absorpt_t_min   0.686
_shelx_estimated_absorpt_t_max   0.786
_shelx_hkl_checksum              63853
_shelx_res_checksum              47813
_cod_database_fobs_code 2243789