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_4027476
_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         'C22 H23 N3 O8 S2'
_chemical_formula_sum            'C22 H23 N3 O8 S2'
_chemical_formula_weight         521.55
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.7918(1)
_cell_length_b                   17.1657(5)
_cell_length_c                   25.0580(17)
_cell_measurement_reflns_used    7955
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.1
_cell_measurement_theta_min      7.1
_cell_volume                     2491.27(19)
_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      173(2)
_diffrn_detector_type
'RAPID II large area curved imaging plate detector '
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku rapid II RAXIS conversion'
_diffrn_measurement_method       'profile data from \w-scans'
_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  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0530
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10781
_diffrn_reflns_theta_full        49.99
_diffrn_reflns_theta_max         49.99
_diffrn_reflns_theta_min         7.07
_exptl_absorpt_coefficient_mu    2.390
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.747
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'FS_ABSCOR (Rigaku, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_description       needle
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881; 1024 Friedel pairs (coverage = 1)'
_refine_ls_abs_structure_Flack   0.02(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.215
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         2542
_refine_ls_number_restraints     66
_refine_ls_restrained_S_all      1.219
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0516
_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^)+(0.0751P)^2^+1.4827P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1695
_reflns_number_gt                1888
_reflns_number_total             2542
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301563j_si_002_7.cif
_cod_data_source_block           compound_5e
_cod_database_code               4027476