Iridium-Catalyzed Intermolecular Amidation of sp(3) C-H Bonds: Late-Stage Functionalization of an Unactivated Methyl Group.
Kang, Taek; Kim, Youngchan; Lee, Donggun; Wang, Zhen; Chang, Sukbok; Journal of the American Chemical Society 136 (2014) 4141–4144; doi:10.1021/ja501014b

data_4121474
_publ_section_title
;
 Iridium-Catalyzed Intermolecular Amidation of sp(3) C-H Bonds: Late-Stage
 Functionalization of an Unactivated Methyl Group.
;
_journal_issue                   11
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4141
_journal_page_last               4144
_journal_paper_doi               10.1021/ja501014b
_journal_volume                  136
_journal_year                    2014
_chemical_absolute_configuration syn
_chemical_formula_moiety         C23H30N2O5S1
_chemical_formula_sum            'C23 H30 N2 O5 S'
_chemical_formula_weight         446.55
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.762(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.0914(4)
_cell_length_b                   10.2457(5)
_cell_length_c                   11.6359(6)
_cell_measurement_reflns_used    10308
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.11
_cell_measurement_theta_min      1.75
_cell_volume                     1082.60(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_sigmaI/netI    0.0710
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10308
_diffrn_reflns_theta_full        27.11
_diffrn_reflns_theta_max         27.11
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  0.9870
_exptl_absorpt_correction_T_min  0.9598
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platy
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.13(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.761
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4607
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.760
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0476
_refine_ls_shift/su_max          0.038
_refine_ls_shift/su_mean         0.008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1294P)^2^+0.4012P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1254
_refine_ls_wR_factor_ref         0.1515
_reflns_number_gt                3669
_reflns_number_total             4607
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja501014b_si_004.cif
_cod_data_source_block           0071b-1
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P21
_cod_database_code               4121474