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_4037867
_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         'C16 H17 F N2 O Se'
_chemical_formula_sum            'C16 H17 F N2 O Se'
_chemical_formula_weight         351.27
_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
_cell_angle_alpha                90
_cell_angle_beta                 92.826(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.2768(6)
_cell_length_b                   20.0266(9)
_cell_length_c                   15.2838(7)
_cell_measurement_reflns_used    2664
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      62.2
_cell_measurement_theta_min      3.5
_cell_volume                     1613.2(2)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      295
_diffrn_detector                 Pilatus100K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.1956
_diffrn_reflns_av_unetI/netI     0.1990
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10835
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        66.764
_diffrn_reflns_theta_max         66.764
_diffrn_reflns_theta_min         3.641
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    3.248
_exptl_absorpt_correction_T_max  0.723
_exptl_absorpt_correction_T_min  0.409
_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    1.446
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          .14
_exptl_crystal_size_mid          .11
_exptl_crystal_size_min          .08
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.901
_refine_diff_density_rms         0.192
_refine_ls_extinction_coef       0.0021(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.801
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2847
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.801
_refine_ls_R_factor_all          0.1886
_refine_ls_R_factor_gt           0.0730
_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^)+(0.0966P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1576
_refine_ls_wR_factor_ref         0.2099
_reflns_Friedel_coverage         0.000
_reflns_number_gt                979
_reflns_number_total             2847
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03045_si_004.cif
_cod_data_source_block           fin1438
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4037867
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              23825
_shelx_hkl_checksum              6174