Pharmaceutical salts of venetoclax with dicarboxylic and sulfonic acids: solid-state characterization and dissolution performance
Havl°ujová, Tereza; Hriňová, Erika; Zmeškalová, Eliška; Kučeráková, Monika; Ridvan, Luděk; Šoóš, Miroslav; CrystEngComm 27 (2025) 1816–1829; doi:10.1039/D4CE01121J

data_7249957
_publ_section_title
;
 Pharmaceutical salts of venetoclax with dicarboxylic and sulfonic acids:
 solid-state characterization and dissolution performance
;
_journal_issue                   12
_journal_name_full               CrystEngComm
_journal_page_first              1816
_journal_page_last               1829
_journal_paper_doi               10.1039/D4CE01121J
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C49 H55 Cl1 N8 O11 S1'
_chemical_formula_sum            'C49 H55 Cl N8 O11 S'
_chemical_formula_weight         999.54
_chemical_name_systematic        Venetoclax
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_update_record
;
2024-08-15 deposited with the CCDC.	2025-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                71.723(3)
_cell_angle_beta                 85.508(3)
_cell_angle_gamma                73.590(3)
_cell_formula_units_Z            2
_cell_length_a                   11.1533(4)
_cell_length_b                   12.6185(5)
_cell_length_c                   19.2633(7)
_cell_measurement_reflns_used    8218
_cell_measurement_temperature    120
_cell_measurement_theta_max      28.62
_cell_measurement_theta_min      2.73
_cell_volume                     2469.28(17)
_computing_cell_refinement
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.872
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_av_unetI/netI     0.052
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            18873
_diffrn_reflns_theta_full        26.167
_diffrn_reflns_theta_max         28.745
_diffrn_reflns_theta_min         2.358
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1052
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.485
_exptl_crystal_size_mid          0.234
_exptl_crystal_size_min          0.143
_refine_diff_density_max         1.56
_refine_diff_density_min         -0.73
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9906
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     651
_refine_ls_number_reflns         11173
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0529
_refine_ls_shift/su_max          0.0004229
_refine_ls_shift/su_mean         0.0000391
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.10P)^2^ + 0.00P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1648
_refine_ls_wR_factor_gt          0.1449
_refine_ls_wR_factor_ref         0.1648
_reflns_limit_h_max              15
_reflns_limit_h_min              -14
_reflns_limit_k_max              16
_reflns_limit_k_min              -15
_reflns_limit_l_max              25
_reflns_limit_l_min              0
_reflns_number_gt                7533
_reflns_number_total             11173
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.25
_oxford_diffrn_Wilson_scale      0.01
_oxford_refine_ls_r_factor_ref   0.0840
_oxford_refine_ls_scale          3.19(3)
_oxford_reflns_number_all        11173
_cod_data_source_file            d4ce01121j2.cif
_cod_data_source_block           I_CCDC2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7249955--7249959.cif.
;
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C49 H55 Cl1 N8 O11 S1'
_cod_database_code               7249957
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_oxford_refine_ls_r_factor_all   0.0840
_oxford_refine_ls_wr_factor_all  0.1648