Enantioselective Mannich Reactions of 3-Fluorooxindoles with Cyclic N-Sulfamidate Aldimines.
Zhao, Jianbo; Li, Ya; Chen, Ling-Yan; Ren, Xinfeng; The Journal of organic chemistry 84 (2019) 5099–5108; doi:10.1021/acs.joc.9b00007

data_4034353
_publ_section_title
;
 Enantioselective Mannich Reactions of 3-Fluorooxindoles with Cyclic
 N-Sulfamidate Aldimines.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5099
_journal_page_last               5108
_journal_paper_doi               10.1021/acs.joc.9b00007
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H15 F N2 O4 S'
_chemical_formula_weight         362.37
_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
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2019-03-20 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7598(3)
_cell_length_b                   11.9832(3)
_cell_length_c                   16.0074(4)
_cell_measurement_reflns_used    5250
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      54.931
_cell_measurement_theta_min      5.761
_cell_volume                     1680.30(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8401
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         2.880
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
; 
 Flack x determined using 1192 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.13(4)
_refine_ls_extinction_coef       0.056(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3276
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0347
_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^)+(0.0558P)^2^+0.0189P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0944
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                3008
_reflns_number_total             3276
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {180f0790-3945-4dce-ac2b-0b44bef8f174}
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
_cod_data_source_file            jo9b00007_si_002.cif
_cod_data_source_block           mo_dd18294_0m
_cod_database_code               4034353
_shelx_estimated_absorpt_t_min   0.960
_shelx_estimated_absorpt_t_max   0.971
_shelxl_version_number           2013-4
_shelx_res_checksum              60656
_shelx_hkl_checksum              63059
_publcif_funding_html
;
;