Ligand-Controlled Regiodivergent Catalytic Amidation of Unactivated Secondary Alkyl Bromides
Tortajada, Andreu; Menezes Correia, Jose Tiago; Serrano, Eloisa; Monleón, Alicia; Tampieri, Alberto; Day, Craig S.; Juliá-Hernández, Francisco; Martin, Ruben; ACS Catalysis 11 (2021) 10223–10227; doi:10.1021/acscatal.1c02913

data_4518984
_publ_section_title
;
 Ligand-Controlled Regiodivergent Catalytic Amidation of Unactivated
 Secondary Alkyl Bromides
;
_journal_issue                   16
_journal_name_full               'ACS Catalysis'
_journal_page_first              10223
_journal_page_last               10227
_journal_paper_doi               10.1021/acscatal.1c02913
_journal_volume                  11
_journal_year                    2021
_chemical_formula_sum            'C32 H40 N4 Ni'
_chemical_formula_weight         539.39
_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   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 102.933(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.2651(13)
_cell_length_b                   8.0978(6)
_cell_length_c                   20.5663(16)
_cell_measurement_reflns_used    9961
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.53
_cell_measurement_theta_min      2.42
_cell_volume                     2802.4(4)
_computing_cell_refinement       'Bruker APEX2 v2014.9-0'
_computing_data_collection       'Bruker APEX2 v2014.9-0'
_computing_data_reduction        'Bruker APEX2 v2014.9-0'
_computing_molecular_graphics
;
 SHELXle: C.B. Huebschle, G.M. Sheldrick & B. Dittrich
 J.Appl.Cryst. (2011) 44, 1281-1284.
;
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution
;
  SHELXT V2018/2 (Sheldrick 2018); G.M. Sheldrick (2015)
 "SHELXT - Integrated space-group and crystal-structure
 determination", Acta Cryst., A71, 3-8. 
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            58430
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.945
_diffrn_reflns_theta_min         2.032
_diffrn_source                   'Microfocus source E025 IuS'
_diffrn_source_current           0.6
_diffrn_source_power             50
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_source_type              'Bruker APEX DUO'
_exptl_absorpt_coefficient_mu    0.720
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_correction_T_min  0.6464
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2014/4
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.567
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         11254
_refine_ls_number_restraints     246
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0338P)^2^+2.0623P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1106
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7661
_reflns_number_total             11254
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c02913_si_003.cif
_cod_data_source_block           mo_CSD0589_0m
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4518984
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.715
_shelx_estimated_absorpt_t_max   0.979
_shelx_res_checksum              10541
_shelx_hkl_checksum              32368