Catalytic asymmetric oxidative carbonylation-induced kinetic resolution of sterically hindered benzylamines to chiral isoindolinones.
Mu, Qiu-Qi; Nie, Yi-Xue; Li, Hang; Bai, Xing-Feng; Liu, Xue-Wei; Xu, Zheng; Xu, Li-Wen; Chemical communications (Cambridge, England) 57 (2021) 1778–1781; doi:10.1039/d0cc07218d

data_7127826
_publ_section_title
;
 Catalytic asymmetric oxidative carbonylation-induced kinetic resolution
 of sterically hindered benzylamines to chiral isoindolinones.
;
_journal_issue                   14
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1778
_journal_page_last               1781
_journal_paper_doi               10.1039/d0cc07218d
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C21 H23 N O4 S'
_chemical_formula_sum            'C21 H23 N O4 S'
_chemical_formula_weight         385.46
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-12-10 deposited with the CCDC.	2021-01-07 downloaded from the CCDC.
;
_cell_angle_alpha                77.459(2)
_cell_angle_beta                 83.636(2)
_cell_angle_gamma                81.818(2)
_cell_formula_units_Z            2
_cell_length_a                   6.8902(4)
_cell_length_b                   11.3752(7)
_cell_length_c                   12.5546(8)
_cell_measurement_reflns_used    9928
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      70.71
_cell_measurement_theta_min      3.62
_cell_volume                     947.48(10)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.945
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16811
_diffrn_reflns_point_group_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.702
_diffrn_reflns_theta_min         3.619
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.744
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7276
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1343 before and 0.0446 after correction. The Ratio of minimum to maximum transmission is 0.7276. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3367
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0369
_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^)+(0.0518P)^2^+0.2688P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1019
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3246
_reflns_number_total             3367
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc07218d2.cif
_cod_data_source_block           cu190930c
_cod_depositor_comments          'Adding full bibliography for 7127826.cif.'
_cod_database_code               7127826
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.722
_shelx_estimated_absorpt_t_min   0.670
_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:
 C8(H8), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              12745
_olex2_submission_special_instructions 'No special instructions were received'