Silver(I)-Catalyzed Atroposelective Desymmetrization of N-Arylmaleimide via 1,3-Dipolar Cycloaddition of Azomethine Ylides: Access to Octahydropyrrolo[3,4-c]pyrrole Derivatives.
Liu, Hua-Chao; Tao, Hai-Yan; Cong, Hengjiang; Wang, Chun-Jiang; The Journal of organic chemistry 81 (2016) 3752–3760; doi:10.1021/acs.joc.6b00396

data_4031972
_publ_section_title
;
 Silver(I)-Catalyzed Atroposelective Desymmetrization of N-Arylmaleimide
 via 1,3-Dipolar Cycloaddition of Azomethine Ylides: Access to
 Octahydropyrrolo[3,4-c]pyrrole Derivatives.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3752
_journal_page_last               3760
_journal_paper_doi               10.1021/acs.joc.6b00396
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H25 Cl N2 O4'
_chemical_formula_sum            'C24 H25 Cl N2 O4'
_chemical_formula_weight         440.91
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 118.361(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.203(4)
_cell_length_b                   5.8478(9)
_cell_length_c                   20.613(4)
_cell_measurement_reflns_used    4872
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      63.64
_cell_measurement_theta_min      4.17
_cell_volume                     2249.1(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'Bruker Kappa APEX-Duo CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_sigmaI/netI    0.0550
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7174
_diffrn_reflns_theta_full        64.57
_diffrn_reflns_theta_max         64.57
_diffrn_reflns_theta_min         2.44
_exptl_absorpt_coefficient_mu    1.774
_exptl_absorpt_correction_T_max  0.9165
_exptl_absorpt_correction_T_min  0.6754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2012/1 (Bruker,2012)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       bar
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     332
_refine_ls_number_reflns         2778
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0593
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0984P)^2^+1.4407P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1559
_refine_ls_wR_factor_ref         0.1624
_reflns_number_gt                2511
_reflns_number_total             2778
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b00396_si_002.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 4031972.cif.'
_cod_original_cell_volume        2249.0(7)
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4031972