The Enantioselective Addition of 1-Fluoro-1-nitro(phenylsulfonyl)methane to Isatin-Derived Ketimines
Urban, Michal; Franc, Michael; Hofmanova, Marketa; Cisarova, Ivana; Vesely, Jan; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB02408H

data_7155932
_publ_section_title
;
 The Enantioselective Addition of 1-Fluoro-1-nitro(phenylsulfonyl)methane
 to Isatin-Derived Ketimines
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB02408H
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesized by the authors'
_chemical_formula_moiety         'C27 H26 F N3 O7 S'
_chemical_formula_sum            'C27 H26 F N3 O7 S'
_chemical_formula_weight         555.57
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2017-09-20 deposited with the CCDC.
2017-10-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.0330(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   27.2206(7)
_cell_length_b                   8.3665(2)
_cell_length_c                   13.1113(3)
_cell_measurement_reflns_used    9946
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      77.3279
_cell_measurement_theta_min      3.9473
_cell_volume                     2727.13(12)
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_collection       'Bruker Instrument Service vV6.2.1'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'XT, VERSION 2014/5'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'Helios Cu  multilayer optic'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            46990
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.474
_diffrn_reflns_theta_min         3.556
_diffrn_source                   'I\mS  micro-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.549
_exptl_absorpt_correction_T_max  0.87
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       prism
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.294
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.091
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 2582 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(7)
_refine_ls_extinction_coef       0.00161(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         5761
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0258
_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^)+(0.0384P)^2^+1.1845P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0674
_refine_ls_wR_factor_ref         0.0677
_reflns_Friedel_coverage         0.854
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                5691
_reflns_number_total             5761
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob02408h2.cif
_cod_data_source_block           cu_mu568_vesely
_cod_database_code               7155932
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.659
_shelx_estimated_absorpt_t_max   0.872
_shelx_res_checksum              22379