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_4035026
_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                 92.807(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.104(6)
_cell_length_b                   9.016(5)
_cell_length_c                   16.057(8)
_cell_measurement_reflns_used    1273
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      38.239
_cell_measurement_theta_min      5.080
_cell_volume                     1605.6(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0734
_diffrn_reflns_av_unetI/netI     0.1322
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9157
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         1.836
_exptl_absorpt_coefficient_mu    0.896
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.3156
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_refine_diff_density_max         1.226
_refine_diff_density_min         -0.718
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details
; 
 Flack x determined using 1217 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         5702
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.1092
_refine_ls_R_factor_gt           0.0739
_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^)+(0.0789P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1665
_refine_ls_wR_factor_ref         0.1893
_reflns_Friedel_coverage         0.787
_reflns_Friedel_fraction_full    0.907
_reflns_Friedel_fraction_max     0.902
_reflns_number_gt                3840
_reflns_number_total             5702
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01336_si_001.cif
_cod_data_source_block           cd15070_0m
_cod_original_cell_volume        1605.6(14)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4035026
_shelx_estimated_absorpt_t_min   0.855
_shelx_estimated_absorpt_t_max   0.908
_shelxl_version_number           2013-4
_shelx_res_checksum              75542
_shelx_hkl_checksum              61981