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_7130018
_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
'C39 H56 N4 Nd O4, 3(C F3 O3 S), C4 H10 O, 3(C H4 O)'
_chemical_formula_sum            'C49 H78 F9 N4 Nd O17 S3'
_chemical_formula_weight         1406.57
_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-2018/3
_audit_update_record
;
2022-03-13 deposited with the CCDC.	2022-04-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.8630(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.9119(5)
_cell_length_b                   20.9804(9)
_cell_length_c                   13.0380(5)
_cell_measurement_reflns_used    9451
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      2.27
_cell_volume                     3134.3(2)
_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 (Sheldrick 2008)'
_diffrn_ambient_temperature      140(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            183057
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.545
_diffrn_reflns_theta_min         2.272
_exptl_absorpt_coefficient_mu    1.021
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9313
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_description       block
_exptl_crystal_F_000             1450
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: MeOH, Ether'
_exptl_crystal_size_max          0.418
_exptl_crystal_size_mid          0.226
_exptl_crystal_size_min          0.156
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.674
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
; 
 Flack x determined using 6693 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.002(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     787
_refine_ls_number_reflns         14436
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0225
_refine_ls_R_factor_gt           0.0216
_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^)+(0.0178P)^2^+1.5935P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0485
_refine_ls_wR_factor_ref         0.0500
_reflns_Friedel_coverage         0.946
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                14154
_reflns_number_total             14436
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc01656g2.cif
_cod_data_source_block           loy023
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7130018
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.675
_shelx_estimated_absorpt_t_max   0.857
_shelx_res_checksum              75195