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_7249733
_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+, C7 H7 O3 S 1-'
_chemical_formula_sum            'C14 H13 F3 N2 O5 S'
_chemical_formula_weight         378.32
_chemical_name_common            Flu.D-PTSA(2:2)
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.2994(2)
_cell_length_b                   7.4757(5)
_cell_length_c                   14.7336(10)
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_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.5
_cell_measurement_theta_min      2.765
_cell_volume                     3227.2(3)
_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 0.997
_diffrn_measured_fraction_theta_max 0.960
_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  0.0281
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            27143
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.475
_diffrn_reflns_theta_min         2.725
_exptl_absorpt_coefficient_mu    0.262
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6678
_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    1.557
_exptl_crystal_description       plate
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.270
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 3166 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     477
_refine_ls_number_reflns         8872
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0329
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0308P)^2^+0.7958P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0679
_refine_ls_wR_factor_ref         0.0726
_reflns_Friedel_coverage         0.816
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.842
_reflns_number_gt                7791
_reflns_number_total             8872
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00979g2.cif
_cod_data_source_block           KB1376_0m
_cod_depositor_comments
'Adding full bibliography for 7249729--7249736.cif.'
_cod_database_code               7249733
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.923
_shelx_estimated_absorpt_t_max   0.933
_shelx_res_checksum              78591
_shelx_hkl_checksum              74173