Enantioselective Regiodivergent Synthesis of Chiral Pyrrolidines with Two Quaternary Stereocenters via Ligand-Controlled Cop-per(I)-Catalyzed Asymmetric 1,3-Dipolar Cycloadditions.
Xu, Shan; Zhang, Zhan-Ming; Xu, Bing; Liu, Bing; Liu, Yuanyuan; Zhang, Junliang; Journal of the American Chemical Society  (2018) –; doi:10.1021/jacs.7b12137

data_4127075
_publ_section_title
;
 Enantioselective Regiodivergent Synthesis of Chiral Pyrrolidines with Two
 Quaternary Stereocenters via Ligand-Controlled Cop-per(I)-Catalyzed
 Asymmetric 1,3-Dipolar Cycloadditions.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b12137
_journal_year                    2018
_chemical_absolute_configuration ad
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_chemical_formula_weight         518.75
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 117.960(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.803(2)
_cell_length_b                   8.0763(8)
_cell_length_c                   13.3188(14)
_cell_measurement_reflns_used    3324
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.6
_cell_measurement_theta_min      2.72
_cell_volume                     2166.5(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
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_diffrn_reflns_limit_k_min       -9
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_exptl_absorpt_correction_T_min  0.4990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.231
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_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
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_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0369P)^2^+0.0786P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0871
_reflns_number_gt                2806
_reflns_number_total             3487
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja7b12137_si_002.cif
_cod_data_source_block           z
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        2166.6(4)
_cod_original_sg_symbol_H-M      C2
_cod_database_code               4127075