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_7249958
_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_absolute_configuration ad
_chemical_formula_moiety         'C66 H66 Cl1 N7.50 O13 S3'
_chemical_formula_sum            'C66 H66 Cl N7.5 O13 S3'
_chemical_formula_weight         1303.94
_chemical_name_systematic        Venetoclax
_space_group_IT_number           1
_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
;
2024-10-25 deposited with the CCDC.	2025-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                84.7041(9)
_cell_angle_beta                 83.8240(9)
_cell_angle_gamma                76.7040(10)
_cell_formula_units_Z            1
_cell_length_a                   10.80160(10)
_cell_length_b                   10.82230(10)
_cell_length_c                   14.07950(10)
_cell_measurement_reflns_used    45301
_cell_measurement_temperature    95
_cell_measurement_theta_max      73.11
_cell_measurement_theta_min      4.17
_cell_volume                     1588.57(2)
_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      95
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.036
_diffrn_reflns_av_unetI/netI     0.041
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            54398
_diffrn_reflns_theta_full        69.634
_diffrn_reflns_theta_max         73.299
_diffrn_reflns_theta_min         3.165
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.038
_exptl_absorpt_correction_T_max  0.83
_exptl_absorpt_correction_T_min  0.40
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             683.500
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetonitrile'
_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.094
_refine_diff_density_max         0.70
_refine_diff_density_min         -0.33
_refine_ls_abs_structure_details
; 
 Parsons, Flack & Wagner (2013), 
 0 Friedel Pairs 
;
_refine_ls_abs_structure_Flack   0.
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0468
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     830
_refine_ls_number_reflns         11525
_refine_ls_number_restraints     1122
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0552
_refine_ls_shift/su_max          0.0003361
_refine_ls_shift/su_mean         0.0000262
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.13P)^2^ + 0.41P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1501
_refine_ls_wR_factor_gt          0.1495
_refine_ls_wR_factor_ref         0.1501
_reflns_limit_h_max              13
_reflns_limit_h_min              -12
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              17
_reflns_limit_l_min              -17
_reflns_number_gt                11444
_reflns_number_total             11525
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.65
_oxford_diffrn_Wilson_scale      0.03
_oxford_refine_ls_r_factor_ref   0.0555
_oxford_refine_ls_scale          5.93(12)
_oxford_reflns_number_all        11525
_cod_data_source_file            d4ce01121j2.cif
_cod_data_source_block           I_CCDC3
_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        'C66 H66 Cl1 N7.50 O13 S3'
_cod_database_code               7249958
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_oxford_refine_ls_r_factor_all   0.0555
_oxford_refine_ls_wr_factor_all  0.1501
_oxford_hooft_y                  0.
_oxford_bijvoet_difference       0.
_oxford_refined_flack_x          0.008(9)