Atroposelective synthesis of isoquinolinone bearing two distinct C−N axes via cobalt-catalyzed enantioselective C−H activation/annulation
Li, Wenkai; Fu, Liling; Xu, Yongqiang; Zhou, Yuhan; Qu, Jingping; Wang, Baomin; Chemical Communications  (2025) –; doi:10.1039/D5CC05883J

data_7135228
_publ_section_title
;
 Atroposelective synthesis of isoquinolinone bearing two distinct
 C&#x2212;N axes via cobalt-catalyzed enantioselective C&#x2212;H
 activation/annulation
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D5CC05883J
_journal_year                    2025
_chemical_formula_moiety         'C23 H21 N O4 S'
_chemical_formula_sum            'C23 H21 N O4 S'
_chemical_formula_weight         407.47
_chemical_name_systematic        4
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-05-19
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-10-15 deposited with the CCDC.	2025-11-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.295(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.927(6)
_cell_length_b                   15.272(8)
_cell_length_c                   13.800(6)
_cell_measurement_reflns_used    2975
_cell_measurement_temperature    143.00
_cell_measurement_theta_max      23.50
_cell_measurement_theta_min      2.48
_cell_volume                     2058.5(19)
_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      143.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1235
_diffrn_reflns_av_unetI/netI     0.0671
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            37166
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.738
_diffrn_reflns_theta_min         2.007
_diffrn_source_current           1.6
_diffrn_source_power             0.08
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5993
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1785 before and 0.1013 after correction.
The Ratio of minimum to maximum transmission is 0.8040.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.678
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4346
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_gt           0.0531
_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^)+(0.0564P)^2^+1.7204P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1264
_refine_ls_wR_factor_ref         0.1513
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2875
_reflns_number_total             4346
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc05883j2.cif
_cod_data_source_block           2_CCDC1
_cod_original_cell_volume        2058.6(18)
_cod_database_code               7135228
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.929
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00B(H00B), C00C(H00C), C00E(H00E), C00F(H00F), C00G(H00G),
 C00I(H00I), C00J(H00J), C00K(H00K), C00M(H00M), C00N(H00N), C00O(H00O),
 C00P(H00P), C00Q(H00Q), C00R(H00R)
2.b Idealised Me refined as rotating group:
 C00S(H00D,H00H,H00L), C00T(H00S,H00T,H00U)
;
_shelx_res_checksum              42331
_shelx_hkl_checksum              76748
_olex2_submission_special_instructions 'No special instructions were received'