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_4127077
_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.
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_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b12137
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C23 H22 Br F3 N2 O5'
_chemical_formula_weight         543.34
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 96.629(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5499(6)
_cell_length_b                   19.6382(11)
_cell_length_c                   11.6438(6)
_cell_measurement_reflns_used    6613
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.50
_cell_measurement_theta_min      2.20
_cell_volume                     2396.2(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Smart Apex II CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
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_diffrn_reflns_limit_h_max       12
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_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
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_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            28187
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_exptl_absorpt_coefficient_mu    1.775
_exptl_absorpt_correction_T_max  0.7892
_exptl_absorpt_correction_T_min  0.5919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.015(7)
_refine_ls_extinction_method     none
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_refine_ls_number_reflns         8208
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_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0453
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0371P)^2^+1.1167P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1123
_reflns_number_gt                6020
_reflns_number_total             8208
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja7b12137_si_003.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_sg_symbol_H-M      P2(1)
_cod_database_code               4127077