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_7249731
_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+, C H3 O3 S 1-'
_chemical_formula_sum            'C8 H9 F3 N2 O5 S'
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_chemical_name_common            FluD-MSA(2:2)
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_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
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_audit_update_record
;
2024-09-26 deposited with the CCDC.	2024-12-12 downloaded from the CCDC.
;
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_cell_measurement_theta_min      2.88
_cell_volume                     2294.4(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'
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_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  0.0398
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.986
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_diffrn_reflns_limit_h_max       15
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_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            57350
_diffrn_reflns_point_group_measured_fraction_full 0.984
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_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.618
_diffrn_reflns_theta_min         2.712
_exptl_absorpt_coefficient_mu    0.344
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_exptl_absorpt_correction_T_min  0.6891
_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
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_exptl_crystal_description       plate
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
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_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.07(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         6971
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.163
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0314
_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^)+(0.0262P)^2^+3.6781P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0808
_reflns_Friedel_coverage         0.995
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                6919
_reflns_number_total             6971
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00979g2.cif
_cod_data_source_block           kb1362_0m_pl
_cod_depositor_comments
'Adding full bibliography for 7249729--7249736.cif.'
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7249731
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.901
_shelx_estimated_absorpt_t_max   0.934
_shelx_res_checksum              79748
_shelx_hkl_checksum              63036