Ullmann-type C-Se cross-coupling in the hydantoin family: Synthesis, mechanistic studies, and tests of biological activity.
Vyhivskyi, Oleksandr; Laikov, Dimitri N.; Finko, Alexander V.; Skvortsov, Dmitry A.; Zhirkina, Irina V.; Tafeenko, Victor Aleksandrovich; Zyk, Nikolay Vasil'evich; Majouga, Alexander G.; Beloglazkina, Elena K.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03045

data_4037868
_publ_section_title
;
 Ullmann-type C-Se cross-coupling in the hydantoin family: Synthesis,
 mechanistic studies, and tests of biological activity.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03045
_journal_year                    2020
_chemical_formula_moiety         'C27 H20 F3 N3 O3 Se'
_chemical_formula_sum            'C27 H20 F3 N3 O3 Se'
_chemical_formula_weight         570.42
_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-2013
_cell_angle_alpha                79.430(3)
_cell_angle_beta                 82.686(4)
_cell_angle_gamma                73.523(3)
_cell_formula_units_Z            2
_cell_length_a                   6.8326(3)
_cell_length_b                   11.2722(4)
_cell_length_c                   17.3205(8)
_cell_measurement_reflns_used    3213
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      64.25
_cell_measurement_theta_min      4.14
_cell_volume                     1253.49(9)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      295
_diffrn_detector                 Pilatus100K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  STOE
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0788
_diffrn_reflns_av_unetI/netI     0.1048
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13284
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         68.099
_diffrn_reflns_theta_min         4.140
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    2.531
_exptl_absorpt_correction_T_max  0.463
_exptl_absorpt_correction_T_min  0.211
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          .16
_exptl_crystal_size_mid          .14
_exptl_crystal_size_min          .12
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.736
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4330
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.736
_refine_ls_R_factor_all          0.1179
_refine_ls_R_factor_gt           0.0390
_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^)+(0.0318P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0721
_refine_ls_wR_factor_ref         0.0864
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1847
_reflns_number_total             4330
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03045_si_003.cif
_cod_data_source_block           fin1147
_cod_database_code               4037868
_shelxl_version_number           2013-4
_shelx_res_checksum              45481
_shelx_hkl_checksum              31661