Diastereoselective Mannich Reactions Using Fluorinated Ketones: Synthesis of Stereogenic Carbon-Fluorine Units.
Li, Ya; Li, Xiang; Shang, Huaqi; Chen, Xiangyu; Ren, Xinfeng; The Journal of organic chemistry 81 (2016) 9858–9866; doi:10.1021/acs.joc.6b01979

data_4037320
_publ_section_title
;
 Diastereoselective Mannich Reactions Using Fluorinated Ketones: Synthesis
 of Stereogenic Carbon-Fluorine Units.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9858
_journal_page_last               9866
_journal_paper_doi               10.1021/acs.joc.6b01979
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C21 H24 F N O2 S'
_chemical_formula_weight         373.47
_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                 102.26(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.926(8)
_cell_length_b                   10.565(10)
_cell_length_c                   11.841(12)
_cell_measurement_reflns_used    1564
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      52.467
_cell_measurement_theta_min      5.221
_cell_volume                     968.9(17)
_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 0.963
_diffrn_measured_fraction_theta_max 0.963
_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  0.0509
_diffrn_reflns_av_unetI/netI     0.0711
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4627
_diffrn_reflns_point_group_measured_fraction_full 0.859
_diffrn_reflns_point_group_measured_fraction_max 0.857
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_min         1.760
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
; 
 Flack x determined using 736 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.04(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3079
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0409
_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=exp[1.0000(sin\q/\l)^2^)]/[\s^2^(Fo^2^)+(0.0326P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0903
_reflns_Friedel_coverage         0.680
_reflns_Friedel_fraction_full    0.742
_reflns_Friedel_fraction_max     0.737
_reflns_number_gt                2277
_reflns_number_total             3079
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01979_si_003.cif
_cod_data_source_block           cd16526
_cod_original_cell_volume        969.0(17)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4037320
_shelx_estimated_absorpt_t_min   0.963
_shelx_estimated_absorpt_t_max   0.981
_shelxl_version_number           2013-4
_shelx_res_checksum              3344
_shelx_hkl_checksum              10089