It takes two to tango: synthesis of cytotoxic quinones containing two redox active centers with potential antitumor activity
Lima, Daisy J. B.; Almeida, Renata G.; Jardim, Guilherme A. M.; Barbosa, Breno P. A.; Santos, Augusto C. C.; Valença, Wagner O.; Scheide, Marcos R.; Gatto, Claudia C.; de Carvalho, Guilherme G. C.; Costa, Pedro M. S.; Pessoa, Claudia; Pereira, Cynthia L. M.; Jacob, Claus; Braga, Antonio L.; da Silva Júnior, Eufrânio N.; RSC Medicinal Chemistry  (2021) –; doi:10.1039/D1MD00168J

data_7243434
_publ_section_title
;
 It takes two to tango: synthesis of cytotoxic quinones containing two
 redox active centers with potential antitumor activity
;
_journal_name_full               'RSC Medicinal Chemistry'
_journal_paper_doi               10.1039/D1MD00168J
_journal_year                    2021
_chemical_formula_moiety         'C16 H15 N3 O3'
_chemical_formula_sum            'C16 H15 N3 O3'
_chemical_formula_weight         297.31
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/4
_audit_update_record
;
2020-02-17 deposited with the CCDC.	2021-08-11 downloaded from the CCDC.
;
_cell_angle_alpha                96.739(6)
_cell_angle_beta                 103.567(6)
_cell_angle_gamma                91.493(6)
_cell_formula_units_Z            2
_cell_length_a                   7.890(4)
_cell_length_b                   9.750(5)
_cell_length_c                   9.847(5)
_cell_measurement_reflns_used    1264
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.2075
_cell_measurement_theta_min      2.6597
_cell_volume                     730.2(6)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker Instrument Service v2018.1.0.3'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0773
_diffrn_reflns_av_unetI/netI     0.0705
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11855
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.430
_diffrn_reflns_theta_min         2.107
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.4097
_exptl_absorpt_correction_type   numerical
_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            orange
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.488
_exptl_crystal_size_mid          0.363
_exptl_crystal_size_min          0.044
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.016(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2686
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1096
_refine_ls_R_factor_gt           0.0514
_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^)+(0.0505P)^2^+0.0510P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1505
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1416
_reflns_number_total             2686
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1md00168j2.cif
_cod_data_source_block           shelx_CCDC2
_cod_database_code               7243434
_shelx_estimated_absorpt_t_min   0.955
_shelx_estimated_absorpt_t_max   0.996
_shelx_res_checksum              93415