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_4134612
_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_moiety
'6(C28 H26 N4 F12 S Se, C6H14, 0.5(C5H12), 0.5(C3H6O)'
_chemical_formula_sum            'C178 H179 F72 N24 O0.5 S6 Se6'
_chemical_formula_weight         4696.56
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-10-18 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.493(6)
_cell_length_b                   29.212(8)
_cell_length_c                   36.334(11)
_cell_measurement_reflns_used    9092
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.40
_cell_measurement_theta_min      2.35
_cell_volume                     22812(11)
_computing_cell_refinement       'Bruker APEX3 (Bruker, 2014)'
_computing_data_collection       'Bruker APEX3 (Bruker, 2014)'
_computing_data_reduction        'Bruker Apex3 SAINT (Bruker, 2014)'
_computing_molecular_graphics    'XP in SHELXTL-plus, Bruker 2014'
_computing_publication_material  'SHELXL2014/7, Sheldrick, G. M. 2014'
_computing_structure_refinement  'SHELXL2014/7, Sheldrick G. M. 2014'
_computing_structure_solution    'SHELXL2014/7, Sheldrick G. M. 2014'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_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  0.1488
_diffrn_reflns_av_unetI/netI     0.1909
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            232491
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         1.625
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.126
_exptl_absorpt_correction_T_max  0.9530
_exptl_absorpt_correction_T_min  0.8165
_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    1.367
_exptl_crystal_description       needle
_exptl_crystal_F_000             9468
_exptl_crystal_size_max          0.358
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.050
_exptl_transmission_factor_max   0.7460
_exptl_transmission_factor_min   0.5834
_refine_diff_density_max         1.096
_refine_diff_density_min         -0.918
_refine_diff_density_rms         0.112
_refine_ls_abs_structure_details
; 
 Flack x determined using 8783 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.039(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2547
_refine_ls_number_reflns         51802
_refine_ls_number_restraints     2129
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.1539
_refine_ls_R_factor_gt           0.0719
_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^)+(0.0828P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1654
_refine_ls_wR_factor_ref         0.1846
_reflns_Friedel_coverage         0.872
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                26926
_reflns_number_total             51802
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b12457_si_002.cif
_cod_data_source_block           fu06
_cod_original_formula_sum        'C178 H179 F72 N24 O0.50 S6 Se6'
_cod_database_code               4134612
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.689
_shelx_estimated_absorpt_t_max   0.946
_shelx_res_checksum              17520
_shelx_hkl_checksum              79305