A diastereoselective Mannich-type reaction of α-fluorinated carboxylate esters: synthesis of β-amino acids containing α-quaternary fluorinated carbon centers.
Li, Xiang; Li, Ya; Shang, Huaqi; Organic & biomolecular chemistry 14 (2016) 6457–6462; doi:10.1039/c6ob01084a

data_7155146
_publ_section_title
;
 A diastereoselective Mannich-type reaction of \a-fluorinated carboxylate
 esters: synthesis of \b-amino acids containing \a-quaternary fluorinated
 carbon centers.
;
_journal_issue                   27
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6457
_journal_page_last               6462
_journal_paper_doi               10.1039/c6ob01084a
_journal_volume                  14
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C23 H28 F N O3 S'
_chemical_formula_weight         417.52
_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-2013
_audit_update_record
;
2016-04-12 deposited with the CCDC.
2016-06-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.548(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.6209(17)
_cell_length_b                   10.0531(16)
_cell_length_c                   10.7441(18)
_cell_measurement_reflns_used    2046
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      41.589
_cell_measurement_theta_min      5.572
_cell_volume                     1137.2(3)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0256
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6578
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_min         1.912
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6279
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.170
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_refine_diff_density_max         0.272
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
; 
 Flack x determined using 1360 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.04(5)
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         4070
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0511
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0572P)^2^+0.1889P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1222
_reflns_Friedel_coverage         0.815
_reflns_Friedel_fraction_full    0.927
_reflns_Friedel_fraction_max     0.922
_reflns_number_gt                3566
_reflns_number_total             4070
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob01084a2.cif
_cod_data_source_block           cd16133
_cod_depositor_comments
'Adding full bibliography for 7155146--7155147.cif.'
_cod_database_code               7155146
_shelx_estimated_absorpt_t_min   0.965
_shelx_estimated_absorpt_t_max   0.980
_shelxl_version_number           2013-4
_shelx_res_checksum              30363