Bifunctional Thiourea-Ammonium Salt Catalysts Derived from Cinchona Alkaloids: Cooperative Phase-Transfer Catalysts in the Enantioselective Aza-Henry Reaction of Ketimines.
Lu, Ning; Fang, Yanhong; Gao, Yuan; Wei, Zhonglin; Cao, Jungang; Liang, Dapeng; Lin, Yingjie; Duan, Haifeng; The Journal of organic chemistry 83 (2018) 1486–1492; doi:10.1021/acs.joc.7b03078

data_4033327
_publ_section_title
;
 Bifunctional Thiourea-Ammonium Salt Catalysts Derived from Cinchona
 Alkaloids: Cooperative Phase-Transfer Catalysts in the Enantioselective
 Aza-Henry Reaction of Ketimines.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1486
_journal_page_last               1492
_journal_paper_doi               10.1021/acs.joc.7b03078
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration S
_chemical_formula_sum            'C18 H20 N2 O6 S'
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_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
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_cell_angle_beta                 90
_cell_angle_gamma                90
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_cell_length_a                   9.815(2)
_cell_length_b                   10.370(2)
_cell_length_c                   19.071(4)
_cell_measurement_reflns_used    2536
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      54.77
_cell_measurement_theta_min      5.96
_cell_volume                     1941.1(7)
_computing_cell_refinement       'Bruker XSCANS'
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_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
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_diffrn_reflns_limit_l_min       -24
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_diffrn_reflns_point_group_measured_fraction_full 0.995
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_diffrn_reflns_theta_max         27.424
_diffrn_reflns_theta_min         2.978
_exptl_absorpt_coefficient_mu    0.203
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_description       block
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_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.210
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_refine_ls_abs_structure_details
;
 Flack x determined using 1041 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_extinction_method     none
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_refine_ls_number_reflns         4395
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0531
_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^)+(0.0421P)^2^+0.3443P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                3297
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_cod_depositor_comments          'Adding full bibliography for 4033327.cif.'
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_shelx_estimated_absorpt_t_max   0.961
_shelx_res_checksum              34135
_shelx_hkl_checksum              37059