Nickel-Catalyzed Decarbonylative Amination of Carboxylic Acid Esters.
Malapit, Christian A.; Borrell, Margarida; Milbauer, Michael W.; Brigham, Conor E.; Sanford, Melanie S.; Journal of the American Chemical Society 142 (2020) 5918–5923; doi:10.1021/jacs.9b13531

data_4134537
_publ_section_title
;
 Nickel-Catalyzed Decarbonylative Amination of Carboxylic Acid Esters.
;
_journal_issue                   13
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5918
_journal_page_last               5923
_journal_paper_doi               10.1021/jacs.9b13531
_journal_volume                  142
_journal_year                    2020
_chemical_formula_moiety         'C38 H58 Ni O P2'
_chemical_formula_sum            'C38 H58 Ni O P2'
_chemical_formula_weight         651.49
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
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_cell_length_c                   16.4162(3)
_cell_measurement_reflns_used    20405
_cell_measurement_temperature    85(2)
_cell_measurement_theta_max      68.8030
_cell_measurement_theta_min      3.6500
_cell_volume                     1711.92(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
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_computing_molecular_graphics    'Bruker SHELXTL'
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_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      85(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
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_diffrn_reflns_limit_k_min       -15
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_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24996
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.305
_diffrn_reflns_theta_min         2.802
_diffrn_source                   'micro-focus rotating anode'
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_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72810
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_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
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_refine_diff_density_min         -0.510
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_refine_ls_extinction_coef       0.0083(4)
_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   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         6173
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0729P)^2^+0.8453P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1115
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6073
_reflns_number_total             6173
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b13531_si_001.cif
_cod_data_source_block           mwm1040
_cod_depositor_comments
'Adding full bibliography for 4134537--4134538.cif.'
_cod_database_code               4134537
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.751
_shelx_estimated_absorpt_t_max   0.833
_shelx_res_checksum              33719
_shelx_hkl_checksum              68195