Synthesis of Chiral β-Fluoroalkyl β-Amino Acid Derivatives via Palladium-Catalyzed Hydrogenation.
Chen, Mu-Wang; Yang, Qin; Deng, Zhihong; Ding, Qiuping; Peng, Yiyuan; The Journal of organic chemistry 84 (2019) 10371–10379; doi:10.1021/acs.joc.9b01523

data_4034012
_publ_section_title
;
 Synthesis of Chiral \b-Fluoroalkyl \b-Amino Acid Derivatives via
 Palladium-Catalyzed Hydrogenation.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10371
_journal_page_last               10379
_journal_paper_doi               10.1021/acs.joc.9b01523
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C12 H14 F3 N O2'
_chemical_formula_weight         261.24
_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   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 91.454(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.4743(13)
_cell_length_b                   5.3473(4)
_cell_length_c                   15.7831(13)
_cell_measurement_reflns_used    7718
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      139.696
_cell_measurement_theta_min      7.902
_cell_volume                     1305.56(18)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17923
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.980
_diffrn_reflns_theta_min         3.951
_exptl_absorpt_coefficient_mu    1.030
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
; 
 Flack x determined using 1396 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.16(9)
_refine_ls_extinction_coef       0.027(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         4539
_refine_ls_number_restraints     41
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0525
_refine_ls_shift/su_max          0.024
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0823P)^2^+0.1452P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1437
_refine_ls_wR_factor_ref         0.1579
_reflns_Friedel_coverage         0.766
_reflns_Friedel_fraction_full    0.940
_reflns_Friedel_fraction_max     0.954
_reflns_number_gt                3666
_reflns_number_total             4539
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01523_si_002.cif
_cod_data_source_block           cu_d8v18760_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4034012
_shelx_estimated_absorpt_t_min   0.828
_shelx_estimated_absorpt_t_max   0.886
_shelxl_version_number           2013-4
_shelx_res_checksum              48219
_shelx_hkl_checksum              46437