Chiral phosphoric acid-catalyzed enantioselective [5+1] cycloaddition reaction of <i>C</i>,<i>N</i>-cyclic azomethine imines with isocyanides.
Yu, Jiulong; Wu, Jinyu; Zhu, Yu; Xiong, Dong; Yang, Lin; Li, Jun; Zheng, Jianfeng; Chemical communications (Cambridge, England) 60 (2024) 2637–2640; doi:10.1039/d3cc05890e

data_7132678
_publ_section_title
;
 Chiral phosphoric acid-catalyzed enantioselective [5+1] cycloaddition
 reaction of <i>C</i>,<i>N</i>-cyclic azomethine imines with isocyanides.
;
_journal_issue                   19
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2637
_journal_page_last               2640
_journal_paper_doi               10.1039/d3cc05890e
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H22 Cl2 N4 O'
_chemical_formula_sum            'C27 H22 Cl2 N4 O'
_chemical_formula_weight         489.38
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2023-06-21 deposited with the CCDC.	2024-02-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.6860(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1692(2)
_cell_length_b                   9.7507(2)
_cell_length_c                   23.6934(5)
_cell_measurement_reflns_used    9779
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      3.81
_cell_volume                     2300.67(8)
_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-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            42371
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.248
_diffrn_reflns_theta_min         3.810
_exptl_absorpt_coefficient_mu    2.767
_exptl_absorpt_correction_T_max  0.9310
_exptl_absorpt_correction_T_min  0.4124
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.549
_exptl_crystal_size_mid          0.107
_exptl_crystal_size_min          0.101
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
; 
 Flack x determined using 3256 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.048(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     621
_refine_ls_number_reflns         8210
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0329
_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^)+(0.0345P)^2^+0.4919P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0759
_refine_ls_wR_factor_ref         0.0783
_reflns_Friedel_coverage         0.840
_reflns_Friedel_fraction_full    0.953
_reflns_Friedel_fraction_max     0.951
_reflns_number_gt                7704
_reflns_number_total             8210
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05890e2.cif
_cod_data_source_block           zjf020
_cod_depositor_comments
'Adding full bibliography for 7132675--7132678.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7132678
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.312
_shelx_estimated_absorpt_t_max   0.767
_shelx_res_checksum              70873
_shelx_hkl_checksum              50767