Asymmetric [3+2]-cyclization of α-imino amide surrogates to construct 3,4-diaminopyrrolidine-2,5-diones.
Ruan, Peiran; Zhang, Cefei; Wu, Jin; Xiao, Fengnan; Zhang, Yongyan; Tan, Qingfa; Su, Zhishan; Feng, Xiaoming; Liu, Xiaohua; Chemical communications (Cambridge, England) 59 (2023) 8250–8253; doi:10.1039/d3cc01203d

data_7131796
_publ_section_title
;
 Asymmetric [3+2]-cyclization of &#x3b1;-imino amide surrogates to
 construct 3,4-diaminopyrrolidine-2,5-diones.
;
_journal_issue                   53
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8250
_journal_page_last               8253
_journal_paper_doi               10.1039/d3cc01203d
_journal_volume                  59
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H31 N3 O5'
_chemical_formula_sum            'C30 H31 N3 O5'
_chemical_formula_weight         513.58
_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-2019/1
_audit_update_record
;
2023-02-02 deposited with the CCDC.	2023-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3754(3)
_cell_length_b                   21.9762(6)
_cell_length_c                   11.2116(3)
_cell_measurement_reflns_used    9912
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.29
_cell_measurement_theta_min      4.02
_cell_volume                     2802.77(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-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.988
_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  0.0556
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17174
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.288
_diffrn_reflns_theta_min         4.023
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7063
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM, PE'
_exptl_crystal_size_max          0.409
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.182
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
; 
 Flack x determined using 2082 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.02(5)
_refine_ls_extinction_coef       0.0071(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         5087
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0413
_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^)+(0.0609P)^2^+0.1987P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.0979
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                4949
_reflns_number_total             5087
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc01203d2.cif
_cod_data_source_block           rpr026
_cod_database_code               7131796
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.769
_shelx_estimated_absorpt_t_max   0.886
_shelx_res_checksum              73460
_shelx_hkl_checksum              36531