Cobalt-Catalyzed and Lewis Acid-Assisted Nitrile Hydrogenation to Primary Amines: A Combined Effort
Tokmic, Kenan; Jackson, Bailey J.; Salazar, Andrea; Woods, Toby J.; Fout, Alison R.; Journal of the American Chemical Society  (2017) –; doi:10.1021/jacs.7b07368

data_4126409
_publ_contact_author
; 
Alison R. Fout 
University of Illinois 
School of Chemical Sciences 
A406 CLSL, Box 54-6 
600 South Mathews Avenue 
Urbana, Illinois  61801 
USA 
;
_publ_section_title
;
 Cobalt-Catalyzed and Lewis Acid-Assisted Nitrile Hydrogenation to Primary
 Amines: A Combined Effort
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b07368
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C64 H55 Co N5 O P'
_chemical_formula_sum            'C64 H55 Co N5 O P'
_chemical_formula_weight         1000.03
_chemical_name_systematic
; 
? 
;
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
; 
? 
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1921(10)
_cell_length_b                   18.4856(16)
_cell_length_c                   20.7607(14)
_cell_measurement_reflns_used    2217
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      19.08
_cell_measurement_theta_min      2.25
_cell_volume                     5062.8(7)
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2014.9-0 (Bruker, 2014)'
_computing_data_reduction
; 
SAINT V8.34A, XPREP v2014/2, SADABS V2014/5, (Bruker, 2012 & 2014) 
;
_computing_molecular_graphics
; 
SHELXTL v2014-7 (Bruker, 2014), CrystalMaker v2.7.7 (CrystalMaker, 1994) 
;
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'
_computing_structure_refinement  'SHELX-2014-7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELX-2014-7 (Sheldrick, 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Bruker Kappa/ApexII CCD'
_diffrn_measurement_method       'profile data from \f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_wavelength_id  483_2
_diffrn_reflns_av_R_equivalents  0.1408
_diffrn_reflns_av_unetI/netI     0.0987
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            47750
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.394
_diffrn_reflns_theta_min         1.829
_exptl_absorpt_coefficient_mu    0.420
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7751
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker, 2014)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2096
_exptl_crystal_id                483_2
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research) with the (1 -2 3) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.187
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.047
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 'Flack (1983),  4084 Friedels'
_refine_ls_abs_structure_Flack   0.41(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     657
_refine_ls_number_reflns         9271
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0924
_refine_ls_R_factor_gt           0.0539
_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^)+(0.0465P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1164
_reflns_Friedel_coverage         0.808
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                6671
_reflns_number_total             9271
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b07368_si_001.cif
_cod_data_source_block           483_2SA
_cod_database_code               4126409
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.926
_shelx_estimated_absorpt_t_max   0.981
_shelx_res_checksum              62100
_shelx_hkl_checksum              51896