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_1553746
_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_absolute_configuration ad
_chemical_compound_source        synthesis
_chemical_formula_sum            'C15 H17 N3 O4 S'
_chemical_formula_weight         335.38
_chemical_name_systematic
(R)-6-methyl-N-(1-nitro-2-phenylpropan-2-yl)pyridine-2-sulfonamide
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 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                90.00
_cell_angle_beta                 109.429(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.6132(15)
_cell_length_b                   7.4744(14)
_cell_length_c                   12.867(3)
_cell_measurement_reflns_used    2200
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.12
_cell_measurement_theta_min      2.51
_cell_volume                     781.2(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  CCD
_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  0.0225
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5194
_diffrn_reflns_theta_full        25.30
_diffrn_reflns_theta_max         25.30
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  0.9595
_exptl_absorpt_correction_T_min  0.9508
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             352
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2777
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0352
_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^)+(0.0499P)^2^+0.0523P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0874
_reflns_number_gt                2581
_reflns_number_total             2777
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7qo00124j2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_absolute_configuration' value 'AD' was changed
to 'ad' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1553746
_solvent_exptl_crystal_recrystallization_method 'dichloromethane, isopropanol'