Atroposelective [4+1] annulation for the synthesis of isotopic isoindolinones bearing both central and axial chirality.
Gu, Jun; Zhang, Li-Hong; Zhuang, Hong-Feng; He, Ying; Chemical science 16 (2025) 5735–5744; doi:10.1039/d5sc00594a

data_1573996
_publ_section_title
;
 Atroposelective [4+1] annulation for the synthesis of isotopic
 isoindolinones bearing both central and axial chirality.
;
_journal_issue                   13
_journal_name_full               'Chemical science'
_journal_page_first              5735
_journal_page_last               5744
_journal_paper_doi               10.1039/d5sc00594a
_journal_volume                  16
_journal_year                    2025
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C23 H20 N2 O3 S'
_chemical_formula_sum            'C23 H20 N2 O3 S'
_chemical_formula_weight         404.47
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-10-16
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-10-23 deposited with the CCDC.	2025-02-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.84300(10)
_cell_length_b                   12.3300(2)
_cell_length_c                   18.0497(2)
_cell_measurement_reflns_used    9859
_cell_measurement_temperature    193.15
_cell_measurement_theta_max      68.216
_cell_measurement_theta_min      4.343
_cell_volume                     1968.03(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      193.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_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       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            40924
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.217
_diffrn_reflns_theta_min         4.343
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.689
_exptl_absorpt_correction_T_max  0.3201
_exptl_absorpt_correction_T_min  0.2151
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1205 before and 0.0590 after correction.
The Ratio of minimum to maximum transmission is 0.6720.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1499 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.034(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3603
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0251
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0446P)^2^+0.1819P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0668
_refine_ls_wR_factor_ref         0.0672
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3548
_reflns_number_total             3603
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc00594a2.cif
_cod_data_source_block           cu_nlg_mf_0m
_cod_depositor_comments
'Adding full bibliography for 1573995--1573998.cif.'
_cod_database_code               1573996
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.849
_shelx_estimated_absorpt_t_min   0.849
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All O(H) groups, H23A of C23
 At 1.2 times of:
  H14 of C14, H4 of C4, H20 of C20, H17 of C17, H18 of C18, H7 of C7, H3A of
  C3, H22 of C22, H9 of C9, H15 of C15, H19 of C19, H5 of C5, H12 of C12, H13
  of C13, H6 of C6, H1 of C1
2.a Ternary CH refined with riding coordinates:
 C15(H15), C22(H22)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3A), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C12(H12), C13(H13),
 C14(H14), C17(H17), C18(H18), C19(H19), C20(H20)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3), C23(H23A)
;
_shelx_res_checksum              13277
_olex2_submission_special_instructions 'No special instructions were received'