Brønsted Base-Switched Selective Mono- and Dithiolation of Benzamides via Copper Catalysis.
Jiang, Yi; Feng, Yi-Yue; Zou, Jiao-Xia; Lei, Shuai; Hu, Xiao-Ling; Yin, Gao-Feng; Tan, Wen; Wang, Zhen; The Journal of organic chemistry 84 (2019) 10490–10500; doi:10.1021/acs.joc.9b01237

data_4034058
_publ_section_title
;
 Br\/onsted Base-Switched Selective Mono- and Dithiolation of Benzamides
 via Copper Catalysis.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10490
_journal_page_last               10500
_journal_paper_doi               10.1021/acs.joc.9b01237
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C36 H26 Cu N4 O4 S2'
_chemical_formula_sum            'C36 H26 Cu N4 O4 S2'
_chemical_formula_weight         706.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-06-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.450(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.7056(3)
_cell_length_b                   19.3654(9)
_cell_length_c                   10.8728(5)
_cell_measurement_reflns_used    8274
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      66.60
_cell_measurement_theta_min      4.57
_cell_volume                     1547.79(12)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      153.15
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11039
_diffrn_reflns_point_group_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        66.635
_diffrn_reflns_theta_max         66.635
_diffrn_reflns_theta_min         4.262
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.658
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1257 before and 0.0552 after correction. The Ratio of minimum to maximum transmission is 0.7958. 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    1.515
_exptl_crystal_description       block
_exptl_crystal_F_000             726
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         1.669
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.128
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.46(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     425
_refine_ls_number_reflns         5092
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0569
_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^)+(0.1105P)^2^+0.4054P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1434
_refine_ls_wR_factor_ref         0.1464
_reflns_Friedel_coverage         0.815
_reflns_Friedel_fraction_full    0.865
_reflns_Friedel_fraction_max     0.864
_reflns_number_gt                4929
_reflns_number_total             5092
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01237_si_002.cif
_cod_data_source_block           20190319_jiangyi_chonscu_0m_a_pl
_cod_database_code               4034058
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.54(4)
 0.46(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C1'(H1'), C2(H2), C2'(H2'), C3(H3), C3'(H3'), C4(H4), C4'(H4'),
 C8(H8), C8'(H8'), C9(H9), C9'(H9'), C10(H10), C10'(H10'), C11(H11), C11'(H11'),
  C14(H14), C14'(H14'), C15(H15), C15'(H15'), C16(H16), C16'(H16'), C17(H17),
 C17'(H17'), C18(H18), C18'(H18')
;
_shelx_res_checksum              57131
_shelx_hkl_checksum              91923
_olex2_submission_special_instructions 'No special instructions were received'