Construction of chiral Betti base precursors containing a congested quaternary stereogenic center via chiral phosphoric acid-catalyzed arylation of isoindolinone-derived ketimines
Glavač, Danijel; Gredičak, Matija; New Journal of Chemistry 46 (2022) 8760–8764; doi:10.1039/D2NJ00493C

data_7061430
_publ_section_title
;
 Construction of chiral Betti base precursors containing a congested
 quaternary stereogenic center via chiral phosphoric acid-catalyzed
 arylation of isoindolinone-derived ketimines
;
_journal_issue                   18
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              8760
_journal_page_last               8764
_journal_paper_doi               10.1039/D2NJ00493C
_journal_volume                  46
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20 H13 Br Cl N O2'
_chemical_formula_weight         414.67
_space_group_IT_number           92
_space_group_name_Hall           'P 4abw 2nw'
_space_group_name_H-M_alt        'P 41 21 2'
_symmetry_cell_setting           tetragonal
_symmetry_Int_Tables_number      92
_symmetry_space_group_name_Hall  'P 4abw 2nw'
_symmetry_space_group_name_H-M   'P 41 21 2'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2019-04-09T15:39:58-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2021-06-07 deposited with the CCDC.	2022-04-06 downloaded from the CCDC.
;
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_cell_angle_gamma                90
_cell_formula_units_Z            8
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_cell_length_b                   11.3861(2)
_cell_length_c                   27.0350(4)
_cell_measurement_reflns_used    7242
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      75.181
_cell_measurement_theta_min      4.202
_cell_volume                     3504.91(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
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_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0242369
_diffrn_orient_matrix_UB_12      0.1083464
_diffrn_orient_matrix_UB_13      0.0325677
_diffrn_orient_matrix_UB_21      -0.0442946
_diffrn_orient_matrix_UB_22      0.0806112
_diffrn_orient_matrix_UB_23      -0.0417829
_diffrn_orient_matrix_UB_31      -0.1255161
_diffrn_orient_matrix_UB_32      -0.0075075
_diffrn_orient_matrix_UB_33      0.021027
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.055
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            19652
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.743
_diffrn_reflns_theta_min         4.213
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.708
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.5865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_description       prism
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 1307 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.031(9)
_refine_ls_extinction_coef       0.00111(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3646
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0371
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0525P)^2^+1.4322P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.102
_reflns_Friedel_coverage         0.675
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                3425
_reflns_number_total             3646
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj00493c2.cif
_cod_data_source_block           exp_693
_cod_depositor_comments          'Adding full bibliography for 7061430.cif.'
_cod_original_cell_volume        3504.91(13)
_cod_database_code               7061430