Catalytic asymmetric transformation of nitrones and allenes to dihydropyridoindoles via chiral N,N′-dioxide/cobalt(ii) catalysis
Liu, Mohuizi; Xie, Lihua; Hou, Liuzhen; Lin, Lili; Feng, Xiaoming; Chemical Communications  (2022) –; doi:10.1039/D2CC01263D

data_7129982
_publ_section_title
;
 Catalytic asymmetric transformation of nitrones and allenes to
 dihydropyridoindoles via chiral N,N&#x2032;-dioxide/cobalt(ii) catalysis
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC01263D
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H24 Br N O2'
_chemical_formula_sum            'C28 H24 Br N O2'
_chemical_formula_weight         486.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-12-21 deposited with the CCDC.	2022-04-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.468(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.505(3)
_cell_length_b                   8.2528(15)
_cell_length_c                   24.175(5)
_cell_measurement_reflns_used    7934
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.35
_cell_measurement_theta_min      2.39
_cell_volume                     2293.2(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_av_unetI/netI     0.0835
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            21338
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.414
_diffrn_reflns_theta_min         2.393
_exptl_absorpt_coefficient_mu    1.818
_exptl_absorpt_correction_T_max  0.9851
_exptl_absorpt_correction_T_min  0.6050
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Et2O, Hexane'
_exptl_crystal_size_max          0.511
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.136
_refine_diff_density_max         0.726
_refine_diff_density_min         -0.977
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details
; 
 Flack x determined using 2722 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.032(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     581
_refine_ls_number_reflns         9150
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0428
_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^)+(0.0413P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.1093
_reflns_Friedel_coverage         0.825
_reflns_Friedel_fraction_full    0.958
_reflns_Friedel_fraction_max     0.945
_reflns_number_gt                7256
_reflns_number_total             9150
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc01263d2.cif
_cod_data_source_block           pgh022
_cod_depositor_comments
;

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C56 H48 Br2 N2 O4'
_cod_original_formula_weight         972.78
_cod_original_formula_moiety         '2(C28 H24 Br N O2)'
_cod_original_formula_units_Z            2
_cod_original_cell_volume        2293.3(8)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7129982
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.457
_shelx_estimated_absorpt_t_max   0.790
_shelx_res_checksum              60189
_shelx_hkl_checksum              36474