A Selenourea-Thiourea Brønsted Acid Catalyst Facilitates Asymmetric Conjugate Additions of Amines to α,β-Unsaturated Esters.
Lin, Yingfu; Hirschi, William J.; Kunadia, Anuj; Paul, Anirudra; Ghiviriga, Ion; Abboud, Khalil A.; Karugu, Rachael W.; Vetticatt, Mathew J.; Hirschi, Jennifer S.; Seidel, Daniel; Journal of the American Chemical Society 142 (2020) 5627–5635; doi:10.1021/jacs.9b12457

data_4134385
_publ_section_title
;
 A Selenourea-Thiourea Br\/onsted Acid Catalyst Facilitates Asymmetric
 Conjugate Additions of Amines to \a,\b-Unsaturated Esters.
;
_journal_issue                   12
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5627
_journal_page_last               5635
_journal_paper_doi               10.1021/jacs.9b12457
_journal_volume                  142
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C22 H25 Br2 N O2'
_chemical_formula_weight         495.25
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-05-23 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 104.107(2)
_cell_angle_gamma                90
_cell_formula_units_Z            6
_cell_length_a                   19.931(2)
_cell_length_b                   5.9364(7)
_cell_length_c                   27.721(3)
_cell_measurement_reflns_used    9350
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.02
_cell_measurement_theta_min      2.96
_cell_volume                     3181.0(6)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II DUO'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            76809
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         1.053
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.839
_exptl_absorpt_correction_T_max  0.7199
_exptl_absorpt_correction_T_min  0.5229
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
'based on measured indexed crystal faces, Bruker SHELXTL2014 (Sheldrick, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_description       needle
_exptl_crystal_F_000             1500
_exptl_crystal_size_max          0.246
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.109
_refine_diff_density_max         1.326
_refine_diff_density_min         -2.019
_refine_diff_density_rms         0.127
_refine_ls_abs_structure_details
; 
 Flack x determined using 5666 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.024(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.196
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     733
_refine_ls_number_reflns         14594
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.196
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0586
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+19.6944P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1223
_reflns_Friedel_coverage         0.824
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                14006
_reflns_number_total             14594
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b12457_si_003.cif
_cod_data_source_block           fu01
_cod_depositor_comments          'Adding full bibliography for 4134385.cif.'
_cod_original_cell_volume        3181.0(7)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4134385
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.452
_shelx_estimated_absorpt_t_max   0.680
_shelx_res_checksum              93933
_shelx_hkl_checksum              79115