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_4121472
_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 ad
_chemical_formula_moiety         'C38 H60 N2 O3 S'
_chemical_formula_sum            'C38 H60 N2 O3 S'
_chemical_formula_weight         624.94
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.0620(5)
_cell_length_b                   12.0849(10)
_cell_length_c                   48.626(4)
_cell_measurement_reflns_used    3712
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      21.50
_cell_measurement_theta_min      2.38
_cell_volume                     3562.3(5)
_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  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.1365
_diffrn_reflns_av_sigmaI/netI    0.1769
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       60
_diffrn_reflns_limit_l_min       -59
_diffrn_reflns_number            21910
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         0.84
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1368
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.38(16)
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         7022
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.953
_refine_ls_R_factor_all          0.1638
_refine_ls_R_factor_gt           0.0737
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0576P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1326
_refine_ls_wR_factor_ref         0.1749
_reflns_number_gt                3528
_reflns_number_total             7022
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja501014b_si_006.cif
_cod_data_source_block           No1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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      P2(1)2(1)2(1)
_cod_database_code               4121472