Synthesis of quinone imine and sulphur-containing compounds with antitumor and trypanocidal activities: redox and biological implications
Almeida, Renata G.; Valença, Wagner O.; Rosa, Luísa G.; de Simone, Carlos A.; de Castro, Solange L.; Barbosa, Juliana M. C.; Pinheiro, Daniel P.; Paier, Carlos R. K.; de Carvalho, Guilherme G. C.; Pessoa, Claudia; Goulart, Marilia O. F.; Kharma, Ammar; da Silva Júnior, Eufrânio N.; RSC Medicinal Chemistry  (2020) –; doi:10.1039/D0MD00072H

data_7240850
_publ_section_title
;
 Synthesis of quinone imine and sulphur-containing compounds with
 antitumor and trypanocidal activities: redox and biological implications
;
_journal_name_full               'RSC Medicinal Chemistry'
_journal_paper_doi               10.1039/D0MD00072H
_journal_year                    2020
_chemical_formula_sum            'C19 H12 Br N O2'
_chemical_formula_weight         366.21
_chemical_name_systematic
'Ortho-quinones with a ?click? and a pronounced structure -- redox -- biological activity relationship.'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-06-17 deposited with the CCDC.	2020-06-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.868(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.8522(14)
_cell_length_b                   11.2852(10)
_cell_length_c                   8.2232(9)
_cell_measurement_reflns_used    4165
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      31.41
_cell_measurement_theta_min      2.97
_cell_volume                     1563.1(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Ortep3 (Farrugia,1997)'
_computing_publication_material  'WinGX-Routine (Farrugia,1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0893
_diffrn_reflns_av_unetI/netI     0.0831
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            25444
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.540
_diffrn_reflns_theta_min         3.018
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.639
_exptl_absorpt_correction_T_max  0.688
_exptl_absorpt_correction_T_min  0.481
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '(Clark, R. C. & Reid, J. S. (1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.13
_refine_diff_density_max         2.908
_refine_diff_density_min         -1.179
_refine_diff_density_rms         0.170
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.229
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         6419
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.229
_refine_ls_R_factor_all          0.2113
_refine_ls_R_factor_gt           0.1325
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3699
_refine_ls_wR_factor_ref         0.4225
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3051
_reflns_number_total             6419
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0md00072h2.cif
_cod_data_source_block           C2413
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7240850
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              98137