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_2243792
_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
'2C32 H32 Br N2 O2 +, 2C4 H3 O4 -, 0.495C6 H14, 2.01C3 H6 O'
_chemical_formula_moiety
'2(C32 H32 Br N2 O2 +), 2(C4 H3 O4 -), 0.495(C6 H14), 2.01(C3 H6 O)'
_chemical_formula_sum            'C81 H89 Br2 N4 O14'
_chemical_formula_weight         1502.51
_chemical_name_common
;
Bedaquilinium maleate--hexane--acetone (1/0.248/1)
;
_chemical_name_systematic
;[4-(6-bromo-2-methoxyquinolin-3-yl)-3-hydroxy-3-(naphthalen-1-yl)-4-phenylbutyl]dimethylazanium 3-carboxyprop-2-enoate--hexane--acetone
(1/0.248/1)
;
_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     isomor
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 107.6347(18)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   16.0678(9)
_cell_length_b                   13.6440(8)
_cell_length_c                   17.8720(8)
_cell_measurement_reflns_used    9698
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      31.6786
_cell_measurement_theta_min      2.5268
_cell_volume                     3733.9(3)
_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 0.994
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
;
Bruker AXS D8 Quest with PhotonII 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  0.0586
_diffrn_reflns_av_unetI/netI     0.0738
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            73087
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.141
_diffrn_reflns_theta_min         2.392
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_exptl_absorpt_coefficient_mu    1.153
_exptl_absorpt_correction_T_max  0.4978
_exptl_absorpt_correction_T_min  0.4388
_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    1.336
_exptl_crystal_description       block
_exptl_crystal_F_000             1570.1
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.605
_refine_diff_density_min         -0.622
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 3753 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.006(3)
_refine_ls_extinction_coef       0.0034(10)
_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   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     558
_refine_ls_number_reflns         14074
_refine_ls_number_restraints     407
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0466
_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^)+(0.0357P)^2^+1.6623P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1261
_reflns_number_gt                9700
_reflns_number_total             14074
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            tx2038sup1.cif
_cod_data_source_block           acetone_hexane
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               2243792
_shelx_estimated_absorpt_t_min   0.608
_shelx_estimated_absorpt_t_max   0.794
_shelx_hkl_checksum              75112
_shelx_res_checksum              87363
_cod_database_fobs_code 2243792