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_7132677
_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_moiety         'C27 H24 N4 O'
_chemical_formula_sum            'C27 H24 N4 O'
_chemical_formula_weight         420.50
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2021-04-06
_audit_creation_method
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Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
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_audit_update_record
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2021-09-25 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            8
_cell_length_a                   26.264(2)
_cell_length_b                   9.4519(8)
_cell_length_c                   18.6059(14)
_cell_measurement_reflns_used    2030
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.5050
_cell_measurement_theta_min      3.3490
_cell_volume                     4618.8(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -15.00   16.60   0.4000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.3211  -99.0000  -90.0000 79

  2 omega    8.00   78.00   0.4000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       17.5086   57.0000    0.0000 175

  3 omega  -15.00   29.00   0.4000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       17.5086  -19.0000  150.0000 110
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0077266000
_diffrn_orient_matrix_UB_12      0.0490059000
_diffrn_orient_matrix_UB_13      -0.0266773000
_diffrn_orient_matrix_UB_21      -0.0049422000
_diffrn_orient_matrix_UB_22      0.0509963000
_diffrn_orient_matrix_UB_23      0.0270691000
_diffrn_orient_matrix_UB_31      0.0254383000
_diffrn_orient_matrix_UB_32      0.0248648000
_diffrn_orient_matrix_UB_33      -0.0028428000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_av_unetI/netI     0.0567
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_number            4710
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.102
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77181
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4710
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1108
_refine_ls_R_factor_gt           0.0606
_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^)+(0.0709P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1332
_refine_ls_wR_factor_ref         0.1528
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2783
_reflns_number_total             4710
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05890e2.cif
_cod_data_source_block           20210331_s1_lgg_m
_cod_depositor_comments
'Adding full bibliography for 7132675--7132678.cif.'
_cod_original_cell_volume        4618.8(7)
_cod_database_code               7132677
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         c12h12n2o3
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.978
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C5(H5A,H5B), C22(H22A,H22B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C8(H8), C9(H9), C20(H20), C25(H25), C16(H16), C31(H31),
 C28(H28), C19(H19), C18(H18), C30(H30), C17(H17), C29(H29)
;
_shelx_res_checksum              67546
_shelx_hkl_checksum              97988
_olex2_submission_special_instructions 'No special instructions were received'