Catalytic, Asymmetric, and Stereodivergent Synthesis of Non-Symmetric β,β-Diaryl-α-Amino Acids.
Molinaro, Carmela; Scott, Jeremy P.; Shevlin, Michael; Wise, Christopher; Ménard, Alain; Gibb, Andrew; Junker, Ellyn M.; Lieberman, David; Journal of the American Chemical Society 137 (2015) 999–1006; doi:10.1021/ja511872a

data_4123294
_publ_section_title
;
 Catalytic, Asymmetric, and Stereodivergent Synthesis of Non-Symmetric
 \b,\b-Diaryl-\a-Amino Acids.
;
_journal_issue                   2
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              999
_journal_page_last               1006
_journal_paper_doi               10.1021/ja511872a
_journal_volume                  137
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H22 Cl F2 N O4'
_chemical_formula_sum            'C21 H22 Cl F2 N O4'
_chemical_formula_weight         425.84
_chemical_name_systematic
;
methyl (2S,3S)-2-((tert-butoxycarbonyl)amino)-3-(4-chlorophenyl)-3-(3,5-difluorophenyl)propanoate
;
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 104.8054(14)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.3707(4)
_cell_length_b                   5.1424(2)
_cell_length_c                   19.9292(8)
_cell_measurement_reflns_used    8402
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.62
_cell_measurement_theta_min      2.293
_cell_volume                     1027.54(7)
_computing_cell_refinement       'SAINT V8.34A'
_computing_data_collection       'SAINT V8.34A'
_computing_data_reduction        'SAINT V8.34A'
_computing_molecular_graphics    'SHELXL-2014 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker \k-geometry diffractometer'
_diffrn_measurement_method       'phi and omega scans '
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11584
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.682
_diffrn_reflns_theta_min         2.293
_diffrn_source                   'sealed-tube X-ray generator'
_exptl_absorpt_coefficient_mu    2.049
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2003)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_description       rod
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_transmission_factor_max   0.7528
_exptl_transmission_factor_min   0.6364
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1389 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         3627
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0548
_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^)+(0.0725P)^2^+0.6514P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1411
_refine_ls_wR_factor_ref         0.1453
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                3358
_reflns_number_total             3627
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja511872a_si_002.cif
_cod_data_source_block           mdj055c_abs
_cod_depositor_comments          'Adding full bibliography for 4123294.cif.'
_cod_database_code               4123294
_shelx_estimated_absorpt_t_min   0.821
_shelx_estimated_absorpt_t_max   0.960
_shelxl_version_number           2014-3
_shelx_res_checksum              20047
_shelx_hkl_checksum              89332