Palladium-catalyzed distal selective C-H chalcogenation of biphenyl amines.
Zhou, Yunhao; Zheng, Tao; Xu, Yue; Li, Bo; Wang, Yuchi; Mei, Ruhuai; Gu, Linghui; Ma, Wenbo; Chemical communications (Cambridge, England) 59 (2023) 8262–8265; doi:10.1039/d3cc02209a

data_7131792
_publ_section_title
;
 Palladium-catalyzed distal selective C-H chalcogenation of biphenyl
 amines.
;
_journal_issue                   53
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8262
_journal_page_last               8265
_journal_paper_doi               10.1039/d3cc02209a
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C24 H17 Cl N2 O Se'
_chemical_formula_sum            'C24 H17 Cl N2 O Se'
_chemical_formula_weight         463.80
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-19
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-04-14 deposited with the CCDC.	2023-06-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.346(8)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.765(5)
_cell_length_b                   14.171(3)
_cell_length_c                   15.154(4)
_cell_measurement_reflns_used    9928
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      26.015
_cell_measurement_theta_min      2.482
_cell_volume                     4207.4(18)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      300.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0856
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            61269
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.023
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.929
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5247
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0880 before and 0.0525 after correction.
The Ratio of minimum to maximum transmission is 0.7037.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_description       block
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     523
_refine_ls_number_reflns         7380
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0334
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0272P)^2^+1.0537P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0683
_refine_ls_wR_factor_ref         0.0766
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5162
_reflns_number_total             7380
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc02209a2.cif
_cod_data_source_block           mo_cd_glh_mwb_zyh_2_161a_0ma_a
_cod_original_cell_volume        4207.5(17)
_cod_database_code               7131792
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.676
_shelx_estimated_absorpt_t_min   0.560
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3A), C49(H49), C3(H3), C50(H50), C5(H5), C6(H6), C9(H9), C11(H11),
  C12(H12), C14(H14), C15(H15), C16(H16), C17(H17), C22(H22), C23(H23),
 C24(H24), C25(H25), C27(H27), C29(H29), C30(H30), C35(H35), C36(H36), C37(H37),
  C38(H38), C39(H39), C40(H40), C41(H41), C42(H42), C44(H44), C45(H45),
 C46(H46), C47(H47), C48(H48)
;
_shelx_res_checksum              60684
_shelx_hkl_checksum              58445
_olex2_submission_special_instructions 'No special instructions were received'