Identification of a Nitrenoid Reductive Elimination Pathway in Nickel-Catalyzed C–N Cross-Coupling
Simon, Connor M.; Dudra, Samantha L.; McGuire, Ryan T.; Ferguson, Michael J.; Johnson, Erin R.; Stradiotto, Mark; ACS Catalysis 12 (2022) 1475–1480; doi:10.1021/acscatal.1c05386

data_4519296
_publ_section_title
;
 Identification of a Nitrenoid Reductive Elimination Pathway in
 Nickel-Catalyzed C--N Cross-Coupling
;
_journal_issue                   2
_journal_name_full               'ACS Catalysis'
_journal_page_first              1475
_journal_page_last               1480
_journal_paper_doi               10.1021/acscatal.1c05386
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C42 H42 N2 Ni O5 P2 S'
_chemical_formula_sum            'C42 H42 N2 Ni O5 P2 S'
_chemical_formula_weight         807.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 107.865(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_b                   27.1961(9)
_cell_length_c                   12.6870(4)
_cell_measurement_reflns_used    5819
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      69.99
_cell_measurement_theta_min      3.25
_cell_volume                     3932.9(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
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_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0720
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            56247
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.235
_diffrn_reflns_theta_min         3.250
_exptl_absorpt_coefficient_mu    2.355
_exptl_absorpt_correction_T_max  0.9425
_exptl_absorpt_correction_T_min  0.8121
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
;
_exptl_crystal_colour            yellow
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_exptl_crystal_description       fragment
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_exptl_crystal_size_max          0.128
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.055
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.00062(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     488
_refine_ls_number_reflns         7487
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0420
_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^)+(0.0595P)^2^+0.9847P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1169
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6023
_reflns_number_total             7487
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c05386_si_003.cif
_cod_data_source_block           dal2021
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4519296
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.753
_shelx_estimated_absorpt_t_max   0.881
_shelx_res_checksum              9619
_shelx_hkl_checksum              88561