Chiral anthranilic pyrrolidine as custom-made amine catalyst for enantioselective Michael reaction of nitroalkenes with carbonyl compounds.
Oka, Yukari; Tsuzuki, Seiji; Moriyama, Katsuhiko; Chemical communications (Cambridge, England) 57 (2021) 11457–11460; doi:10.1039/d1cc04453b

data_7129061
_publ_section_title
;
 Chiral anthranilic pyrrolidine as custom-made amine catalyst for
 enantioselective Michael reaction of nitroalkenes with carbonyl
 compounds.
;
_journal_issue                   87
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              11457
_journal_page_last               11460
_journal_paper_doi               10.1039/d1cc04453b
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration rmad
_chemical_formula_sum            'C21 H23 F3 N2 O6 S'
_chemical_formula_weight         488.47
_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
_audit_update_record
;
2021-07-22 deposited with the CCDC.	2021-10-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.555(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.1768(16)
_cell_length_b                   7.6356(7)
_cell_length_c                   18.1963(17)
_cell_measurement_reflns_used    9786
_cell_measurement_temperature    173
_cell_measurement_theta_max      68.4108
_cell_measurement_theta_min      2.7342
_cell_volume                     2245.4(4)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEXII Ultra CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            27043
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.706
_diffrn_reflns_theta_min         2.430
_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_exptl_absorpt_coefficient_mu    1.877
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prismatic
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.651
_refine_diff_density_min         -0.315
_refine_ls_abs_structure_details
;
Flack x determined using 3331 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.055(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     644
_refine_ls_number_reflns         7981
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0547
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1118P)^2^+0.4799P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1526
_refine_ls_wR_factor_ref         0.1544
_reflns_Friedel_coverage         0.814
_reflns_Friedel_fraction_full    0.950
_reflns_Friedel_fraction_max     0.939
_reflns_number_gt                7640
_reflns_number_total             7981
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc04453b2.cif
_cod_data_source_block           u20150615mor1
_cod_depositor_comments          'Adding full bibliography for 7129061.cif.'
_cod_database_code               7129061
_shelx_res_checksum              55321