Asymmetric Construction of 3,4-Diamino Pyrrolidines via Chiral N,O-Ligand/Cu(I) Catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides with β-Phthalimidonitroethene.
He, Fu-Sheng; Zhu, Han; Wang, Zheng; Gao, Ming; Yu, Xingxin; Deng, Wei-Ping; Organic letters 17 (2015) 4988–4991; doi:10.1021/acs.orglett.5b02431

data_1555323
_publ_section_title
;
 Asymmetric Construction of 3,4-Diamino Pyrrolidines via Chiral
 N,O-Ligand/Cu(I) Catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides
 with \b-Phthalimidonitroethene.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              4988
_journal_page_last               4991
_journal_paper_doi               10.1021/acs.orglett.5b02431
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20 H16 Cl N3 O6'
_chemical_formula_weight         429.81
_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
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 92.800(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.5669(8)
_cell_length_b                   20.611(2)
_cell_length_c                   7.3177(9)
_cell_measurement_reflns_used    2045
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      48.934
_cell_measurement_theta_min      5.574
_cell_volume                     989.3(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5976
_diffrn_reflns_point_group_measured_fraction_full 0.811
_diffrn_reflns_point_group_measured_fraction_max 0.808
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_min         1.976
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.175
_exptl_crystal_size_mid          0.164
_exptl_crystal_size_min          0.112
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
; 
 Flack x determined using 891 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.03(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3118
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0360
_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^)+(0.0492P)^2^+0.0262P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0908
_reflns_Friedel_coverage         0.572
_reflns_Friedel_fraction_full    0.612
_reflns_Friedel_fraction_max     0.606
_reflns_number_gt                2705
_reflns_number_total             3118
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b02431_si_002.cif
_cod_data_source_block           cd214249
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1555323
_shelxl_version_number           2013-4
_shelx_res_checksum              75495
_shelx_hkl_checksum              75099