The facile and stereoselective synthesis of pyrrolidine β-amino acids via copper(i)-catalyzed asymmetric 1,3-dipolar cycloaddition
He, Fu-Sheng; Li, Cong-Shan; Deng, Hua; Zheng, Xing; Yang, Zhong-Tao; Deng, Wei-Ping; Organic Chemistry Frontiers 4 (2017) 52–; doi:10.1039/C6QO00512H

data_1553556
_publ_section_title
;
 The facile and stereoselective synthesis of pyrrolidine \b-amino acids
 via copper(i)-catalyzed asymmetric 1,3-dipolar cycloaddition
;
_journal_issue                   1
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              52
_journal_paper_doi               10.1039/C6QO00512H
_journal_volume                  4
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C29 H25 Cl N2 O8 S'
_chemical_formula_weight         597.02
_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   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2016-07-25 deposited with the CCDC.
2016-10-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.473(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.4186(19)
_cell_length_b                   9.7011(17)
_cell_length_c                   13.152(2)
_cell_measurement_reflns_used    2386
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      41.813
_cell_measurement_theta_min      4.626
_cell_volume                     1455.5(4)
_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 0.999
_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  0.0294
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8415
_diffrn_reflns_point_group_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.494
_diffrn_reflns_theta_min         1.785
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6221
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             620
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
; 
 Flack x determined using 1621 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         5122
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0670P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1179
_reflns_Friedel_coverage         0.778
_reflns_Friedel_fraction_full    0.888
_reflns_Friedel_fraction_max     0.884
_reflns_number_gt                4341
_reflns_number_total             5122
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00512h2.cif
_cod_data_source_block           cd16374
_cod_original_cell_volume        1455.6(4)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1553556
_shelx_estimated_absorpt_t_min   0.946
_shelx_estimated_absorpt_t_max   0.975
_shelxl_version_number           2013-4
_shelx_res_checksum              80271
_shelx_hkl_checksum              48133