Flutamide degradation driven by sulfonic acids: unforeseen salts and salt polymorphs of a degraded flutamide impurity
Prashanth, Jupally; Pisini, Krishna Prasad; Surampudi, Anuja Venkata Sai Durga; Nechipadappu, Sunil Kumar; Swain, Debasish; Balasubramanian, Sridhar; CrystEngComm 27 (2025) 997–1015; doi:10.1039/D4CE00979G

data_7249732
_publ_section_title
;
 Flutamide degradation driven by sulfonic acids: unforeseen salts and salt
 polymorphs of a degraded flutamide impurity
;
_journal_issue                   7
_journal_name_full               CrystEngComm
_journal_page_first              997
_journal_page_last               1015
_journal_paper_doi               10.1039/D4CE00979G
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety
'C7 H6 F3 N2 O2 1+, 2(C7 H7 O3 S) 2-, 2(H2 O), H3 O 1+'
_chemical_formula_sum            'C21 H27 F3 N2 O11 S2'
_chemical_formula_weight         604.57
_chemical_name_common            'Flu.D-PTSA-H2O (1:2:3)'
_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
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-09-26 deposited with the CCDC.	2024-12-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.428(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.8176(6)
_cell_length_b                   7.4895(4)
_cell_length_c                   17.8098(10)
_cell_measurement_reflns_used    6112
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.4
_cell_measurement_theta_min      2.29
_cell_volume                     1305.63(13)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2016)'
_computing_data_collection       '<i>APEX3</i> (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1081
_diffrn_reflns_av_unetI/netI     0.1079
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            34218
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.353
_diffrn_reflns_theta_min         2.294
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_description       plate
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.608
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details
;
 Flack x determined using 1488 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         6462
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1044
_refine_ls_R_factor_gt           0.0560
_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^)+(0.0385P)^2^+0.9239P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1147
_reflns_Friedel_coverage         0.851
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                4546
_reflns_number_total             6462
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00979g2.cif
_cod_data_source_block           KB1456_0m_a
_cod_depositor_comments
'Adding full bibliography for 7249729--7249736.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7249732
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.916
_shelx_estimated_absorpt_t_max   0.945
_shelx_res_checksum              3005
_shelx_hkl_checksum              33978