Cobalt-catalyzed regio- and stereoselective synthesis of atropisomers with vicinal C-C and C-N diaxes.
Ghosh, Suman; Saha, Partha Sarathi; Saha, Shib Nath; Chandrasekharan, Sanoop P.; Koner, Mainak; Baidya, Mahiuddin; Chemical communications (Cambridge, England) 61 (2025) 15231–15234; doi:10.1039/d5cc04297f

data_7134927
_publ_section_title
;
 Cobalt-catalyzed regio- and stereoselective synthesis of atropisomers
 with vicinal C-C and C-N diaxes.
;
_journal_issue                   78
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              15231
_journal_page_last               15234
_journal_paper_doi               10.1039/d5cc04297f
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C43 H32 N2 O4 S'
_chemical_formula_sum            'C43 H32 N2 O4 S'
_chemical_formula_weight         672.76
_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_block_doi                 10.5517/ccdc.csd.cc2p23qm
_audit_creation_date             2025-06-15
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-07-22 deposited with the CCDC.	2025-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.682(5)
_cell_length_b                   17.405(9)
_cell_length_c                   21.044(10)
_cell_measurement_reflns_used    6687
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      66.24
_cell_measurement_theta_min      3.30
_cell_volume                     3546(3)
_computing_cell_refinement       'APEX4/SAINT (Bruker, 2021)'
_computing_data_collection       'APEX4 (Bruker, 2021)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019), WinGX'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker D8 Venture Diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0773
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            61881
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.081
_diffrn_reflns_theta_max         67.081
_diffrn_reflns_theta_min         3.295
_diffrn_source                   'micro focus sealed tube'
_exptl_absorpt_coefficient_mu    1.175
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5849
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector 
scaling and absorption correction 
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_description       plate
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.504
_exptl_crystal_size_mid          0.213
_exptl_crystal_size_min          0.073
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.17(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     454
_refine_ls_number_reflns         6232
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0575
_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^)+(0.0761P)^2^+0.8616P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1402
_refine_ls_wR_factor_ref         0.1524
_reflns_Friedel_coverage         0.775
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                5250
_reflns_number_total             6232
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc04297f2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7134927.cif.'
_cod_database_code               7134927
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.919
_shelx_estimated_absorpt_t_min   0.589
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.83409
 0.16591
2.a Secondary CH2 refined with riding coordinates:
 C42(H42A,H42B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13),
 C14(H14), C15(H15), C21(H21), C22(H22), C23(H23), C25(H25), C26(H26), C27(H27),
  C30(H30), C31(H31), C33(H33), C37(H37), C38(H38), C39(H39), C40(H40), C41(H41)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C43(H43A,H43B,H43C)
;
_shelx_res_checksum              61340
_shelx_hkl_checksum              68047
_olex2_submission_special_instructions 'No special instructions were received'