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_7132675
_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_formula_sum            'C19 H16 F2 O2'
_chemical_formula_weight         314.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc29hwk8
_audit_update_record
;
2021-12-22 deposited with the CCDC.	2024-02-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.534(2)
_cell_length_b                   12.716(3)
_cell_length_c                   15.945(4)
_cell_measurement_reflns_used    6113
_cell_measurement_temperature    150.(2)
_cell_measurement_theta_max      66.32
_cell_measurement_theta_min      2.77
_cell_volume                     1527.6(7)
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1260)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker D8 VENTURE DUO PHOTON III'
_diffrn_radiation_monochromator  'Helios MX Multilayer Optic'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10659
_diffrn_reflns_theta_full        66.74
_diffrn_reflns_theta_max         66.74
_diffrn_reflns_theta_min         3.48
_diffrn_source                   'Microfocus sealed tube'
_diffrn_source_type              'Incoatec Ius 3.0'
_exptl_absorpt_coefficient_mu    0.870
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_process_details
;
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.215
_refine_ls_abs_structure_details
;

Flack x determined using 913 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2445
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.168
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0318
_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^)+(0.0347P)^2^+0.6455P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0762
_refine_ls_wR_factor_ref         0.0946
_reflns_Friedel_coverage         0.774
_reflns_Friedel_fraction_full    0.826
_reflns_Friedel_fraction_max     0.826
_reflns_number_gt                2276
_reflns_number_total             2445
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05890e2.cif
_cod_data_source_block           20210910a
_cod_depositor_comments
'Adding full bibliography for 7132675--7132678.cif.'
_cod_database_code               7132675
_shelx_res_checksum              3642
_shelx_hkl_checksum              31912