Metal-free Synthesis of Phenol-Aryl Selenides via Dehydrogenative C-Se Coupling of Aryl Selenoxides with Phenols.
Liu, Zhengfen; Jiang, Yonggang; Liu, Chunxiang; Zhang, Linlin; Wang, Jing; Li, Tiantian; Zhang, Hongbin; Li, Minyan; Yang, Xiaodong; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00792

data_4038362
_publ_section_title
;
 Metal-free Synthesis of Phenol-Aryl Selenides via Dehydrogenative C-Se
 Coupling of Aryl Selenoxides with Phenols.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00792
_journal_year                    2020
_chemical_formula_sum            'C15 H11 N O Se'
_chemical_formula_weight         300.20
_space_group_crystal_system      orthorhombic
_space_group_IT_number           45
_space_group_name_Hall           'I 2 -2c'
_space_group_name_H-M_alt        'I b a 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   16.643(3)
_cell_length_b                   21.249(4)
_cell_length_c                   14.381(3)
_cell_measurement_reflns_used    1866
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.8953
_cell_measurement_theta_min      2.4475
_cell_volume                     5085.8(17)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_av_unetI/netI     0.0889
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14133
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.140
_diffrn_reflns_theta_max         25.140
_diffrn_reflns_theta_min         1.554
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.939
_exptl_absorpt_correction_T_max  0.667
_exptl_absorpt_correction_T_min  0.345
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_description       sheet
_exptl_crystal_F_000             2400
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         4431
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0065P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0692
_refine_ls_wR_factor_ref         0.0861
_reflns_Friedel_coverage         0.912
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2784
_reflns_number_total             4431
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00792_si_002.cif
_cod_data_source_block           3ao
_cod_depositor_comments
;

2025-07-29
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum        'C30 H22 N2 O2 Se2'
_cod_original_formula_units_Z    8
_cod_original_formula_weight     600.41
_cod_database_code               4038362
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.345
_shelx_estimated_absorpt_t_max   0.667
_shelx_res_checksum              7921
_shelx_hkl_checksum              52606