Copper-catalyzed intermolecular amidation and imidation of unactivated alkanes.
Tran, Ba L.; Li, Bijie; Driess, Matthias; Hartwig, John F.; Journal of the American Chemical Society 136 (2014) 2555–2563; doi:10.1021/ja411912p

data_4120542
_publ_section_title
;
 Copper-catalyzed intermolecular amidation and imidation of unactivated
 alkanes.
;
_journal_issue                   6
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2555
_journal_page_last               2563
_journal_paper_doi               10.1021/ja411912p
_journal_volume                  136
_journal_year                    2014
_chemical_formula_moiety         'C20 H24 Cu N3 O3 S'
_chemical_formula_sum            'C20 H24 Cu N3 O3 S'
_chemical_formula_weight         450.04
_chemical_name_common            '[(L1)Cu(NHSO2Ph)]'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 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                 110.84(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7344(17)
_cell_length_b                   16.996(2)
_cell_length_c                   12.836(3)
_cell_measurement_reflns_used    1338
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      32.4808
_cell_measurement_theta_min      3.3009
_cell_volume                     1984.7(7)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET)
(compiled Jan 12 2007,17:49:11)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET)
(compiled Jan 12 2007,17:49:11)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET)
(compiled Jan 12 2007,17:49:11)
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 16.3031
_diffrn_measured_fraction_theta_full 0.891
_diffrn_measured_fraction_theta_max 0.891
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur S Sapphire'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0852
_diffrn_reflns_av_sigmaI/netI    0.1064
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7402
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.31
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_type              'Mo Source'
_exptl_absorpt_coefficient_mu    1.232
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.20154
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             932
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         3121
_refine_ls_number_restraints     179
_refine_ls_restrained_S_all      1.158
_refine_ls_R_factor_all          0.1193
_refine_ls_R_factor_gt           0.0840
_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^)+(0.0596P)^2^+0.5978P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1589
_refine_ls_wR_factor_ref         0.1759
_reflns_number_gt                2347
_reflns_number_total             3121
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja411912p_si_005.cif
_cod_data_source_block           ba1.cif
_cod_original_cell_volume        1984.7(6)
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               4120542