Catalytic asymmetric amination of azlactones with azobenzenes
Ke, Chaoqi; Cao, Qiuhui; Luo, Yao; Liu, Xiaohua; Feng, Xiaoming; Chemical Communications  (2022) –; doi:10.1039/D2CC01656G

data_7130017
_publ_section_title
;
 Catalytic asymmetric amination of azlactones with azobenzenes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC01656G
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H24 F N3 O4'
_chemical_formula_sum            'C30 H24 F N3 O4'
_chemical_formula_weight         509.52
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-03-12 deposited with the CCDC.	2022-04-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3838(3)
_cell_length_b                   37.4871(10)
_cell_length_c                   6.6582(2)
_cell_measurement_reflns_used    9924
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      80.28
_cell_measurement_theta_min      4.42
_cell_volume                     2591.76(13)
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.937
_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  0.0532
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_k_min       -46
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            15409
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         80.727
_diffrn_reflns_theta_min         4.418
_exptl_absorpt_coefficient_mu    0.763
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6919
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM, PE'
_exptl_crystal_size_max          0.368
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
; 
 Flack x determined using 2008 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.03(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         5304
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0407
_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^)+(0.0445P)^2^+0.5947P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1068
_reflns_Friedel_coverage         0.715
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.914
_reflns_number_gt                5013
_reflns_number_total             5304
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc01656g2.cif
_cod_data_source_block           ljw014
_cod_database_code               7130017
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.766
_shelx_estimated_absorpt_t_max   0.963
_shelx_res_checksum              79190