Chemical Resolution of C, N-Unprotected α-Substituted β-Amino Acids Using Stable and Recyclable Proline-Derived Chiral Ligands.
Wang, Shuni; Nian, Yong; Zhou, Shengbin; Wang, Jiang; Liu, Hong; The Journal of organic chemistry 83 (2018) 9870–9878; doi:10.1021/acs.joc.8b01336

data_4035025
_publ_section_title
;
 Chemical Resolution of C, N-Unprotected \a-Substituted \b-Amino Acids
 Using Stable and Recyclable Proline-Derived Chiral Ligands.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9870
_journal_page_last               9878
_journal_paper_doi               10.1021/acs.joc.8b01336
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C36 H32 Cl3 N3 Ni O3'
_chemical_formula_weight         719.70
_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
_cell_angle_alpha                90
_cell_angle_beta                 104.977(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.976(7)
_cell_length_b                   8.894(4)
_cell_length_c                   16.293(8)
_cell_measurement_reflns_used    791
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      34.164
_cell_measurement_theta_min      5.261
_cell_volume                     1956.5(16)
_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  0.0920
_diffrn_reflns_av_unetI/netI     0.2004
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10906
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         1.715
_exptl_absorpt_coefficient_mu    0.735
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5326
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_platon_squeeze_details
;
;
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details
; 
 Flack x determined using 909 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.10(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.916
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         6944
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.916
_refine_ls_R_factor_all          0.1605
_refine_ls_R_factor_gt           0.0860
_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^)+(0.0786P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1771
_refine_ls_wR_factor_ref         0.2048
_reflns_Friedel_coverage         0.786
_reflns_Friedel_fraction_full    0.908
_reflns_Friedel_fraction_max     0.903
_reflns_number_gt                3393
_reflns_number_total             6944
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01336_si_002.cif
_cod_data_source_block           cd15068
_cod_original_cell_volume        1956.6(17)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4035025
_shelxl_version_number           2013-4
_shelx_res_checksum              29754
_shelx_hkl_checksum              60824