Regio- and Enantioselective Iridium-Catalyzed Amination of Racemic Branched Alkyl-Substituted Allylic Acetates with Primary and Secondary Aromatic and Heteroaromatic Amines.
Kim, Seung Wook; Schwartz, Leyah A.; Zbieg, Jason R.; Stivala, Craig E.; Krische, Michael J.; Journal of the American Chemical Society 141 (2019) 671–676; doi:10.1021/jacs.8b12152

data_4133649
_publ_section_title
;
 Regio- and Enantioselective Iridium-Catalyzed Amination of Racemic
 Branched Alkyl-Substituted Allylic Acetates with Primary and Secondary
 Aromatic and Heteroaromatic Amines.
;
_journal_issue                   1
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              671
_journal_page_last               676
_journal_paper_doi               10.1021/jacs.8b12152
_journal_volume                  141
_journal_year                    2019
_chemical_formula_sum            'C13 H18 Br Cl N2 O'
_chemical_formula_weight         333.65
_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-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 105.491(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1967(3)
_cell_length_b                   19.2597(4)
_cell_length_c                   10.4450(4)
_cell_measurement_temperature    100(2)
_cell_volume                     1395.15(9)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            21319
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.594
_diffrn_reflns_theta_min         4.393
_exptl_absorpt_coefficient_mu    5.697
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.691
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details
;
 Flack x determined using 2566 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.010(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         5628
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0656P)^2^+0.4659P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.0948
_reflns_Friedel_coverage         0.918
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                5511
_reflns_number_total             5628
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b12152_si_002.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4133649
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.463
_shelx_estimated_absorpt_t_max   0.848
_shelx_res_checksum              24642
_shelx_hkl_checksum              95341