Enantioselective fluorination of 3-indolinone-2-carboxylates with NFSI catalyzed by chiral bisoxazolines.
Banik, Swarnayu; Sahoo, Tanmoy; Sridhar, B.; Subba Reddy, B. V.; Organic & biomolecular chemistry 19 (2021) 6085–6091; doi:10.1039/d1ob00144b

data_7158126
_publ_section_title
;
 Enantioselective fluorination of 3-indolinone-2-carboxylates with NFSI
 catalyzed by chiral bisoxazolines.
;
_journal_issue                   27
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6085
_journal_page_last               6091
_journal_paper_doi               10.1039/d1ob00144b
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C13 H12 F N O4'
_chemical_formula_sum            'C13 H12 F N O4'
_chemical_formula_weight         265.24
_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-2018/3
_audit_update_record
;
2020-12-03 deposited with the CCDC.	2021-06-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7100(7)
_cell_length_b                   9.8223(10)
_cell_length_c                   16.1672(13)
_cell_measurement_reflns_used    5940
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      30.29
_cell_measurement_theta_min      2.48
_cell_volume                     1224.34(19)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2016)'
_computing_data_collection       '<i>APEX3</i> (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  '<i>SHELXL2014</i> (Sheldrick, 2015b)'
_computing_structure_solution    '<i>SHELXT</i> (Sheldrick, 2015a)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11447
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.531
_diffrn_reflns_theta_min         2.426
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4612
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker, 2016'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 871 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(5)
_refine_ls_extinction_coef       0.048(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         3688
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0473
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0598P)^2^+0.1181P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1287
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                2579
_reflns_number_total             3688
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00144b2.cif
_cod_data_source_block           KA1004_0m
_cod_depositor_comments          'Adding full bibliography for 7158126.cif.'
_cod_database_code               7158126
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.970
_shelx_estimated_absorpt_t_max   0.982
_shelx_res_checksum              844