Intermolecular C-H Amination of Complex Molecules: Insights into the Factors Governing the Selectivity
Camille Lescot; Benjamin Darses; Florence Collet; Pascal Retailleau; Philippe Dauban; Journal of Organic Chemistry 77 (2012) 7232–7240; doi:10.1021/jo301563j

data_4027472
_publ_contact_author_address
;Centre de Recherche de Gif
Institut de Chimie des Substances Naturelles
UPR2301-CNRS
B\^at 27
1 avenue de la Terrasse
91198 Gif sur Yvette
France
;
_publ_contact_author_email       philippe.dauban@icsn.cnrs-gif.fr
_publ_contact_author_fax         +33169077247
_publ_contact_author_name        'DAUBAN, Philippe'
_publ_contact_author_phone       +33169824560
_publ_section_title
;
 Intermolecular C-H Amination of Complex Molecules: Insights into the
 Factors Governing the Selectivity
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7232
_journal_page_last               7240
_journal_paper_doi               10.1021/jo301563j
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H30 N2 O3 S2'
_chemical_formula_sum            'C24 H30 N2 O3 S2'
_chemical_formula_weight         458.62
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.462(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.3898(14)
_cell_length_b                   9.7688(8)
_cell_length_c                   12.5363(9)
_cell_measurement_reflns_used    2743
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      65.7
_cell_measurement_theta_min      6.7
_cell_volume                     2469.8(3)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_type
'RAPID II large area curved imaging plate detector '
_diffrn_measured_fraction_theta_full .997
_diffrn_measured_fraction_theta_max .997
_diffrn_measurement_details
;
scan:
    Number of images: 36
               Slice: 20.0000 - 200.0000
         Image width: 5.0000
            Exp time: 360.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 0.0000
                 Phi: 0.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 32
               Slice: 20.0000 - 184.0000
         Image width: 5.0000
            Exp time: 360.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 180.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 32
               Slice: 20.0000 - 182.0000
         Image width: 5.0000
            Exp time: 360.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 270.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 18
               Slice: 42.0000 - 132.0000
         Image width: 5.0000
            Exp time: 360.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 0.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 18
               Slice: 42.0000 - 132.0000
         Image width: 5.0000
            Exp time: 360.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 90.0000
                 XTD: 127.4000
              2theta: 0.0000
;
_diffrn_measurement_device_type  'Rigaku rapid II RAXIS conversion'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_orient_matrix_type       FS_PROCESS
_diffrn_orient_matrix_UB_11      0.085531
_diffrn_orient_matrix_UB_12      -0.001065
_diffrn_orient_matrix_UB_13      -0.000596
_diffrn_orient_matrix_UB_21      0.028303
_diffrn_orient_matrix_UB_22      -0.059481
_diffrn_orient_matrix_UB_23      -0.034247
_diffrn_orient_matrix_UB_31      -0.005425
_diffrn_orient_matrix_UB_32      0.060154
_diffrn_orient_matrix_UB_33      -0.045421
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0707
_diffrn_reflns_av_sigmaI/netI    0.1149
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10068
_diffrn_reflns_theta_full        60.49
_diffrn_reflns_theta_max         60.49
_diffrn_reflns_theta_min         6.65
_exptl_absorpt_coefficient_mu    2.166
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'FS_ABSCOR (Rigaku, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       'thin platelet'
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_refine_diff_density_max         .321
_refine_diff_density_min         -.444
_refine_diff_density_rms         .053
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881;1626 Friedel pairs'
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         3607
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1331
_refine_ls_R_factor_gt           0.0663
_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^)+(0.0759P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1847
_reflns_number_gt                1799
_reflns_number_total             3607
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301563j_si_002_3.cif
_cod_data_source_block           compound_3f
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4027472