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_4034059
_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_formula_moiety         'C48 H34 Cu N4 O4 S4'
_chemical_formula_sum            'C48 H34 Cu N4 O4 S4'
_chemical_formula_weight         922.57
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-09-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
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_cell_length_b                   10.175(2)
_cell_length_c                   15.325(4)
_cell_measurement_reflns_used    716
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.0700
_cell_measurement_theta_min      3.8570
_cell_volume                     1136.0(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega -102.00  -64.00   2.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  178.0000  -90.0000 19

  2 omega  -15.00   25.00   2.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  -99.0000   60.0000 20

  3 omega   -1.00   91.00   2.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000  -60.0000 46

  4 omega  -36.00   86.00   2.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -19.0000  -30.0000 61

  5 omega  -48.00   46.00   2.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000  150.0000 47
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
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_diffrn_orient_matrix_UB_12      -0.0000322000
_diffrn_orient_matrix_UB_13      -0.0415018000
_diffrn_orient_matrix_UB_21      -0.0090664000
_diffrn_orient_matrix_UB_22      0.0710314000
_diffrn_orient_matrix_UB_23      0.0224475000
_diffrn_orient_matrix_UB_31      0.0765561000
_diffrn_orient_matrix_UB_32      0.0227236000
_diffrn_orient_matrix_UB_33      -0.0150841000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0776
_diffrn_reflns_av_unetI/netI     0.1716
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7307
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.485
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.712
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60415
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       needle
_exptl_crystal_F_000             475
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.619
_refine_diff_density_min         -0.580
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         4459
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_refine_ls_R_factor_all          0.1521
_refine_ls_R_factor_gt           0.0731
_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^)+(0.0107P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.1333
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2128
_reflns_number_total             4459
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01237_si_003.cif
_cod_data_source_block           jiangy_0913
_cod_database_code               4034059
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C9(H9), C3(H3), C4(H4), C11(H11), C21(H21), C18(H18),
 C10(H10), C22(H22), C14(H14), C17(H17), C24(H24), C20(H20), C15(H15), C16(H16),
  C23(H23)
;
_shelx_res_checksum              17822
_shelx_hkl_checksum              67860
_shelx_fab_checksum              19321
_olex2_date_sample_data_collection 2018-09-13
_olex2_submission_special_instructions 'No special instructions were received'