Catalytic Olefin Hydroamidation Enabled by Proton-Coupled Electron Transfer.
Miller, David C.; Choi, Gilbert J.; Orbe, Hudson S.; Knowles, Robert R.; Journal of the American Chemical Society 137 (2015) 13492–13495; doi:10.1021/jacs.5b09671

data_4129700
_publ_section_title
;
 Catalytic Olefin Hydroamidation Enabled by Proton-Coupled Electron
 Transfer.
;
_journal_issue                   42
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13492
_journal_page_last               13495
_journal_paper_doi               10.1021/jacs.5b09671
_journal_volume                  137
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H23 N O2'
_chemical_formula_weight         273.36
_chemical_name_common            DCM1
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.3463(4)
_cell_length_b                   14.4931(9)
_cell_length_c                   16.2263(9)
_cell_measurement_reflns_used    5079
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.5080
_cell_measurement_theta_min      4.0898
_cell_volume                     1492.46(16)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'BRUKER APEX II CCD'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10687
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.216
_diffrn_reflns_theta_min         5.452
_diffrn_source                   'ImuS micro--focus source'
_exptl_absorpt_coefficient_mu    0.623
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular rod'
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.173
_exptl_crystal_size_mid          0.044
_exptl_crystal_size_min          0.043
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.4(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2718
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0270
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0414P)^2^+0.1961P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0719
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2611
_reflns_number_total             2718
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b09671_si_002.cif
_cod_data_source_block           cu_PDJDCM1_0m
_cod_database_code               4129700
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.900
_shelx_estimated_absorpt_t_max   0.974
_shelx_res_checksum              24034
_shelx_hkl_checksum              78700