Asymmetric Pd-Catalyzed Alkene Carboamination Reactions for the Synthesis of 2-Aminoindane Derivatives.
White, Derick R.; Hutt, Johnathon T.; Wolfe, John P.; Journal of the American Chemical Society 137 (2015) 11246–11249; doi:10.1021/jacs.5b07203

data_4124309
_publ_section_title
;
 Asymmetric Pd-Catalyzed Alkene Carboamination Reactions for the Synthesis
 of 2-Aminoindane Derivatives.
;
_journal_issue                   35
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11246
_journal_page_last               11249
_journal_paper_doi               10.1021/jacs.5b07203
_journal_volume                  137
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H19 Br N'
_chemical_formula_sum            'C17 H19 Br N'
_chemical_formula_weight         317.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 116.571(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.7101(5)
_cell_length_b                   7.15570(10)
_cell_length_c                   10.9015(8)
_cell_measurement_reflns_used    8312
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      68.20
_cell_measurement_theta_min      4.50
_cell_volume                     1514.69(16)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r16'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r16'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      273(2)
_diffrn_detector_area_resol_mean 14.629
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_laue_measured_fraction_full 0.998
_diffrn_reflns_laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11435
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.202
_diffrn_reflns_theta_min         4.535
_diffrn_source                   'micro-focus rotating anode'
_exptl_absorpt_coefficient_mu    3.569
_exptl_absorpt_correction_T_max  0.836
_exptl_absorpt_correction_T_min  0.702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
; 
 Flack x determined using 1020 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.020(19)
_refine_ls_extinction_coef       0.0035(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2701
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0418
_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^)+(0.0742P)^2^+0.1633P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1112
_reflns_Friedel_coverage         0.790
_reflns_friedel_fraction_full    0.941
_reflns_friedel_fraction_max     0.938
_reflns_number_gt                2501
_reflns_number_total             2701
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b07203_si_002.cif
_cod_data_source_block           dw1a
_cod_depositor_comments          'Adding full bibliography for 4124309.cif.'
_cod_original_cell_volume        1514.69(15)
_cod_database_code               4124309
_shelx_estimated_absorpt_t_min   0.674
_shelx_estimated_absorpt_t_max   0.842
_shelxl_version_number           2014/6
_shelx_res_checksum              96128
_shelx_hkl_checksum              8593