A palladium catalyzed asymmetric desymmetrization approach to enantioenriched 1,3-disubstituted isoindolines.
Dethe, Dattatraya H.; Kumar, Vimlesh; Shukla, Manmohan; Chemical science 14 (2023) 11267–11272; doi:10.1039/d3sc03496h

data_1569941
_publ_section_title
;
 A palladium catalyzed asymmetric desymmetrization approach to
 enantioenriched 1,3-disubstituted isoindolines.
;
_journal_issue                   40
_journal_name_full               'Chemical science'
_journal_page_first              11267
_journal_page_last               11272
_journal_paper_doi               10.1039/d3sc03496h
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C18 H16 F3 N O3 S'
_chemical_formula_sum            'C18 H16 F3 N O3 S'
_chemical_formula_weight         383.38
_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
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-02-24
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-03-31 deposited with the CCDC.	2023-09-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.274(2)
_cell_length_b                   11.716(4)
_cell_length_c                   14.422(4)
_cell_measurement_reflns_used    9399
_cell_measurement_temperature    124.00
_cell_measurement_theta_max      66.764
_cell_measurement_theta_min      4.88
_cell_volume                     1736.0(8)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       'Bruker APEX3 ver.2018.7-2(Bruker AXS)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      124.00
_diffrn_detector                 'CPAD area detector'
_diffrn_detector_area_resol_mean 7.407
_diffrn_detector_type            'Bruker Photon III'
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            40412
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        66.530
_diffrn_reflns_theta_max         66.530
_diffrn_reflns_theta_min         4.863
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_type              'Incoatec I\ms Diamond'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.115
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.4485
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1639 before and 0.0986 after correction. The Ratio of minimum to maximum transmission is 0.5958. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.343
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1257 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.109(5)
_refine_ls_extinction_coef       0.024(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3009
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0317
_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^)+(0.0593P)^2^+0.2961P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.0848
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                2997
_reflns_number_total             3009
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc03496h2.cif
_cod_data_source_block           ups_uk_1163_0m_a
_cod_depositor_comments          'Adding full bibliography for 1569941.cif.'
_cod_database_code               1569941
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.785
_shelx_estimated_absorpt_t_min   0.531
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C23(H23), C22(H22), C19(H19), C4(H4), C6(H6), C7(H7), C20(H20),
 C5(H5)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_shelx_res_checksum              36363
_olex2_submission_special_instructions 'No special instructions were received'