Enantioselective nickel-catalyzed Mizoroki-Heck cyclizations of amide electrophiles.
Bulger, Ana S.; Nasrallah, Daniel J.; Tena Meza, Arismel; Garg, Neil K.; Chemical science 15 (2024) 2593–2600; doi:10.1039/d3sc05797f

data_1570724
_publ_section_title
;
 Enantioselective nickel-catalyzed Mizoroki-Heck cyclizations of amide
 electrophiles.
;
_journal_issue                   7
_journal_name_full               'Chemical science'
_journal_page_first              2593
_journal_page_last               2600
_journal_paper_doi               10.1039/d3sc05797f
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C22 H23 Br N2 O2 S'
_chemical_formula_sum            'C22 H23 Br N2 O2 S'
_chemical_formula_weight         459.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2023-06-21 deposited with the CCDC.	2024-01-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.0090(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5459(2)
_cell_length_b                   19.1854(5)
_cell_length_c                   11.5679(3)
_cell_measurement_reflns_used    8933
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.92
_cell_measurement_theta_min      3.83
_cell_volume                     2115.65(9)
_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'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.986
_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  0.0457
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            26366
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.613
_diffrn_reflns_theta_min         3.826
_diffrn_source                   'I\mS micro--focus source'
_exptl_absorpt_coefficient_mu    3.728
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.64
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_description       irregular
_exptl_crystal_F_000             944
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethanol'
_exptl_crystal_size_max          .18
_exptl_crystal_size_mid          .04
_exptl_crystal_size_min          .04
_refine_diff_density_max         0.796
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
; 
 Flack x determined using 2977 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.009(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     513
_refine_ls_number_reflns         7768
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0329
_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^)+(0.0315P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0700
_refine_ls_wR_factor_ref         0.0712
_reflns_Friedel_coverage         0.916
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                6827
_reflns_number_total             7768
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc05797f2.cif
_cod_data_source_block           cu_garg2304_a
_cod_depositor_comments          'Adding full bibliography for 1570724.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1570724
_shelxl_version_number           2014/6
_shelx_res_checksum              4285