Palladium-Catalyzed Cross-Coupling of Unactivated Alkylzinc Reagents with 2-Bromo-3,3,3-Trifluoropropene: A New Access to Diversified Fluorinated Amino Acids
Zhang, Xingang; Lou, Yue-Guang; Wang, An-Jun; Zhao, Liang; He, Lin-Feng; Li, Xiaofei; He, Chun-Yang; Chemical Communications  (2019) –; doi:10.1039/C8CC10212K

data_7122956
_publ_section_title
;
 Palladium-Catalyzed Cross-Coupling of Unactivated Alkylzinc Reagents with
 2-Bromo-3,3,3-Trifluoropropene: A New Access to Diversified Fluorinated
 Amino Acids
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C8CC10212K
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C11 H20 F3 N O5'
_chemical_formula_weight         303.28
_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_block_doi                 10.5517/ccdc.csd.cc21by0c
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2018-12-26 deposited with the CCDC.
2019-02-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.524(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.6250(2)
_cell_length_b                   9.3524(3)
_cell_length_c                   13.0235(4)
_cell_measurement_reflns_used    5002
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      139.60
_cell_measurement_theta_min      11.747
_cell_volume                     787.73(4)
_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 0.970
_diffrn_measured_fraction_theta_max 0.994
_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  0.0591
_diffrn_reflns_av_unetI/netI     0.0530
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_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            10507
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.494
_diffrn_reflns_theta_min         5.873
_exptl_absorpt_coefficient_mu    1.064
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.4791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
; 
 Flack x determined using 987 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.21(15)
_refine_ls_extinction_coef       0.021(6)
_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   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2741
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0472
_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^)+(0.0621P)^2^+0.0957P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1314
_reflns_Friedel_coverage         0.865
_reflns_Friedel_fraction_full    0.956
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                2416
_reflns_number_total             2741
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc10212k2.cif
_cod_data_source_block           cu_d8v18496_0m
_cod_database_code               7122956
_shelx_estimated_absorpt_t_min   0.865
_shelx_estimated_absorpt_t_max   0.929
_shelxl_version_number           2013-4
_shelx_res_checksum              57525
_shelx_hkl_checksum              3626