Copper-catalyzed regioselective 1,2-thioamidation of alkenes.
Li, Dengke; Mao, Tingting; Huang, Jinbo; Zhu, Qiang; Chemical communications (Cambridge, England) 53 (2017) 3450–3453; doi:10.1039/c7cc00083a

data_7119723
_publ_section_title
;
 Copper-catalyzed regioselective 1,2-thioamidation of alkenes.
;
_journal_issue                   24
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3450
_journal_page_last               3453
_journal_paper_doi               10.1039/c7cc00083a
_journal_volume                  53
_journal_year                    2017
_chemical_formula_moiety         'C30 H30 N2 O7 S3'
_chemical_formula_sum            'C30 H30 N2 O7 S3'
_chemical_formula_weight         626.74
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-01-03
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2017-01-03 deposited with the CCDC.
2017-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                89.3079(16)
_cell_angle_beta                 81.4110(16)
_cell_angle_gamma                84.4246(14)
_cell_formula_units_Z            2
_cell_length_a                   8.86824(15)
_cell_length_b                   10.25459(19)
_cell_length_c                   16.1386(3)
_cell_measurement_reflns_used    21171
_cell_measurement_temperature    116(11)
_cell_measurement_theta_max      66.7130
_cell_measurement_theta_min      4.3300
_cell_volume                     1444.32(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      116(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4015
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega   17.00  116.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.6007   38.0000 -120.0000 99

  2 omega  -31.00   70.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.6007  -57.0000  -30.0000 101

  3 omega    9.00  118.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.6007   77.0000 -180.0000 109

  4 omega    9.00  118.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.6007   77.0000  -90.0000 109

  5 omega   17.00  116.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.6007   38.0000  120.0000 99

  6 omega    9.00  118.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.6007   77.0000    0.0000 109

  7 omega   -3.00   96.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.6007 -125.0000 -150.0000 99

  8 omega    9.00  118.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.6007   77.0000   90.0000 109

  9 omega   19.00   77.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       92.2461  -45.0000 -180.0000 58

 10 omega   60.00  168.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       92.2461   77.0000   90.0000 108

 11 omega   60.00  168.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       92.2461   77.0000  -30.0000 108

 12 omega   60.00  168.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       92.2461   77.0000 -120.0000 108

 13 omega   60.00  168.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       92.2461   77.0000   30.0000 108

 14 omega   60.00  168.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       92.2461   77.0000  -60.0000 108

 15 omega    9.00  129.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       92.2461  -90.0000   -0.0698 120

 16 omega   60.00  168.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       92.2461   77.0000 -180.0000 108

 17 omega   60.00  168.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       92.2461   77.0000 -150.0000 108

 18 omega   60.00  168.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       92.2461   77.0000 -180.0000 108

 19 omega   60.00  168.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       92.2461   77.0000   60.0000 108

 20 omega   60.00  168.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       92.2461   77.0000  120.0000 108

 21 omega   60.00  168.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       92.2461   77.0000    0.0000 108

 22 omega   19.00   77.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       92.2461  -45.0000  120.0000 58

 23 omega   60.00  168.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       92.2461   77.0000  -90.0000 108

 24 omega   60.00  168.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       92.2461   77.0000  150.0000 108

 25 omega   19.00   77.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       92.2461  -45.0000   30.0000 58

 26 omega   63.00  165.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       92.2461   61.0000  120.0000 102

 27 omega    9.00  130.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       92.2461  -91.0000  -74.0285 121

 28 omega    9.00  130.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       92.2461  -92.0000  146.1765 121

 29 omega -118.00   -9.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6007  -77.0000 -150.0000 109

 30 omega  -98.00  -18.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6007  125.0000 -180.0000 80

 31 omega -115.00  -13.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6007  -57.0000   30.0000 102

 32 omega  -47.00  130.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.6007    0.0000 -180.0000 177

 33 omega  -47.00  130.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.6007    0.0000  -90.0000 177

 34 omega   13.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.6007   57.0000 -180.0000 102

 35 omega   13.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.6007   57.0000   60.0000 102

 36 omega  -47.00  130.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.6007    0.0000 -150.0000 177

 37 omega  -47.00  130.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.6007    0.0000 -120.0000 177

 38 omega    9.00  118.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.6007   77.0000 -150.0000 109

 39 omega   19.00   77.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       92.2461  -45.0000  -30.0000 58

 40 omega   62.00  166.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       92.2461   69.0000  -91.9123 104

 41 omega   63.00  165.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       92.2461   61.0000  150.0000 102

 42 omega   63.00  165.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       92.2461   61.0000 -150.0000 102

 43 omega   63.00  165.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       92.2461   61.0000 -180.0000 102

 44 omega   66.00  165.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       92.2461   45.0000  -30.0000 99

 45 omega   63.00  165.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       92.2461   61.0000   90.0000 102

 46 omega   63.00  165.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       92.2461   61.0000   60.0000 102

 47 omega   63.00  165.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       92.2461   61.0000    0.0000 102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0888651000
_diffrn_orient_matrix_UB_12      0.1134544000
_diffrn_orient_matrix_UB_13      0.0220589000
_diffrn_orient_matrix_UB_21      0.1485970000
_diffrn_orient_matrix_UB_22      -0.0932176000
_diffrn_orient_matrix_UB_23      -0.0086523000
_diffrn_orient_matrix_UB_31      0.0343168000
_diffrn_orient_matrix_UB_32      0.0349749000
_diffrn_orient_matrix_UB_33      -0.0935882000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            43502
_diffrn_reflns_theta_full        62.38
_diffrn_reflns_theta_max         62.38
_diffrn_reflns_theta_min         2.77
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.783
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.598
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         4598
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0409
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0510P)^2^+1.3541P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1087
_reflns_number_gt                4069
_reflns_number_total             4598
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7cc00083a2.cif
_cod_data_source_block           exp_879
_cod_depositor_comments          'Adding full bibliography for 7119723.cif.'
_cod_database_code               7119723
_chemical_oxdiff_formula         'C616 H963 N193 O182 S10'
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     62.30
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C29(H29A,H29B), C37(H37A,H37B), C39(H39A,H39B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C13(H13), C15(H15), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21), C25(H25), C27(H27), C30(H30), C31(H31), C33(H33), C34(H34),
  C35(H35), C36(H36)
2.d Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C)
;
_olex2_date_sample_data_collection 2016-12-28
_olex2_submission_special_instructions 'No special instructions were received'