Highly enantioselective nitro-Mannich reaction of ketimines under phase-transfer catalysis
Wang, Bin; Xu, Tong; Zhu, Lei; Lan, Yu; Wang, Jingdong; Lu, Ning; Wei, Zhonglin; Lin, Yingjie; Duan, Haifeng; Organic Chemistry Frontiers 4 (2017) 1266–; doi:10.1039/C7QO00124J

data_1553745
_publ_section_title
;
 Highly enantioselective nitro-Mannich reaction of ketimines under
 phase-transfer catalysis
;
_journal_issue                   7
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1266
_journal_paper_doi               10.1039/C7QO00124J
_journal_volume                  4
_journal_year                    2017
_chemical_compound_source        synthesis
_chemical_formula_moiety         'C14 H14 N2 O2 S'
_chemical_formula_sum            'C14 H14 N2 O2 S'
_chemical_formula_weight         274.33
_chemical_name_systematic
(E)-6-methyl-N-(1-phenylethylidene)pyridine-2-sulfonamide
_chemical_properties_physical    ', Moisture-sensitive'
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-06-27 deposited with the CCDC.
2017-03-20 downloaded from the CCDC.
;
_cell_angle_alpha                83.14(2)
_cell_angle_beta                 79.60(2)
_cell_angle_gamma                72.93(2)
_cell_formula_units_Z            2
_cell_length_a                   6.121(5)
_cell_length_b                   8.835(7)
_cell_length_c                   13.265(12)
_cell_measurement_reflns_used    2335
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.16
_cell_measurement_theta_min      1.56
_cell_volume                     672.8(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_sigmaI/netI    0.0631
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4111
_diffrn_reflns_theta_full        25.16
_diffrn_reflns_theta_max         25.16
_diffrn_reflns_theta_min         1.56
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  0.9610
_exptl_absorpt_correction_T_min  0.9548
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2335
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.967
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0655
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1435P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1851
_refine_ls_wR_factor_ref         0.2162
_reflns_number_gt                1533
_reflns_number_total             2335
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7qo00124j2.cif
_cod_data_source_block           sad
_cod_original_sg_symbol_H-M      p-1
_cod_database_code               1553745
_solvent_exptl_crystal_recrystallization_method 'dichloromethane, iso-propanol'