Chelate-assisted direct selenation of aryl C-h bonds with diselenides catalyzed by palladium.
Iwasaki, Masayuki; Tsuchiya, Yuta; Nakajima, Kiyohiko; Nishihara, Yasushi; Organic letters 16 (2014) 4920–4923; doi:10.1021/ol502439m

data_1517906
_publ_section_title
;
 Chelate-assisted direct selenation of aryl C-h bonds with diselenides
 catalyzed by palladium.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4920
_journal_page_last               4923
_journal_paper_doi               10.1021/ol502439m
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C23 H18 N2 O Se'
_chemical_formula_sum            'C23 H18 N2 O Se'
_chemical_formula_weight         417.35
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.049(2)
_cell_length_b                   14.884(5)
_cell_length_c                   16.221(7)
_cell_measurement_reflns_used    12513
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      3.01
_cell_volume                     1943.3(12)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_publication_material  'CrystalStructure 4.0'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_sigmaI/netI    0.0330
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18158
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    1.947
_exptl_absorpt_correction_T_max  0.6968
_exptl_absorpt_correction_T_min  0.5928
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.015
_refine_diff_density_min         -0.932
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.007(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4445
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0559
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0505P)^2^+2.2055P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1402
_reflns_number_gt                3353
_reflns_number_total             4445
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol502439m_si_002.cif
_cod_data_source_block           yn35
_cod_original_cell_volume        1943.1(12)
_cod_database_code               1517906