Diastereo- and Enantioselective Synthesis of Homoallylic Amines Bearing Quaternary Carbon Centers.
Green, Jacob C.; Zanghi, Joseph M.; Meek, Simon J.; Journal of the American Chemical Society 142 (2020) 1704–1709; doi:10.1021/jacs.9b11529

data_4134002
_publ_section_title
;
 Diastereo- and Enantioselective Synthesis of Homoallylic Amines Bearing
 Quaternary Carbon Centers.
;
_journal_issue                   4
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1704
_journal_page_last               1709
_journal_paper_doi               10.1021/jacs.9b11529
_journal_volume                  142
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H24 Br1 N1 O1'
_chemical_formula_sum            'C20 H24 Br N O'
_chemical_formula_weight         374.32
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.84220(10)
_cell_length_b                   9.8585(2)
_cell_length_c                   31.3192(6)
_cell_measurement_reflns_used    9057
_cell_measurement_temperature    100
_cell_measurement_theta_max      67
_cell_measurement_theta_min      4
_cell_volume                     1803.84(6)
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'USER DEFINED STRUCTURE SOLUTION'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       Serial
_diffrn_measurement_device_type  Unknown
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.035
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            25646
_diffrn_reflns_theta_full        61.936
_diffrn_reflns_theta_max         66.598
_diffrn_reflns_theta_min         2.822
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.125
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.54
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.224
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_min          0.091
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.22
_refine_ls_abs_structure_details
; 
 Parsons, Flack & Wagner (2013), 
 1273 Friedel Pairs 
;
_refine_ls_abs_structure_Flack   0.022(7)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3143
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0209
_refine_ls_R_factor_gt           0.0201
_refine_ls_shift/su_max          0.0020269
_refine_ls_shift/su_mean         0.0000401
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.02P)^2^ + 0.93P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0470
_refine_ls_wR_factor_gt          0.0467
_refine_ls_wR_factor_ref         0.0470
_reflns_limit_h_max              6
_reflns_limit_h_min              -6
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              37
_reflns_limit_l_min              0
_reflns_number_gt                3067
_reflns_number_total             3143
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0209
_oxford_refine_ls_scale          0.4914(4)
_oxford_reflns_number_all        3143
_cod_data_source_file            ja9b11529_si_002.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 4134002.cif.'
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C20 H24 Br1 N1 O1'
_cod_database_code               4134002
_oxford_refine_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_hooft_y                  0.015(6)
_oxford_bijvoet_difference       0.022(7)
_oxford_refined_flack_x          0.016(13)