Asymmetric synthesis of quaternary alpha-fluoro-beta-keto-amines via detrifluoroacetylative Mannich reactions
Chen Xie; Yanling Dai; Haibo Mei; Jianlin Han; Vadim A. Soloshonok; Yi Pan; Chem.Commun. 51 (2015) 9149–; doi:10.1039/C5cc02256H

data_7117190
_publ_section_title
;
 Asymmetric synthesis of quaternary alpha-fluoro-beta-keto-amines via
 detrifluoroacetylative Mannich reactions
;
_journal_name_full               Chem.Commun.
_journal_page_first              9149
_journal_paper_doi               10.1039/C5cc02256H
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H21 F4 N O4 S'
_chemical_formula_sum            'C17 H21 F4 N O4 S'
_chemical_formula_weight         411.41
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-02-09 deposited with the CCDC.
2015-04-23 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7459(6)
_cell_length_b                   9.8069(8)
_cell_length_c                   25.6020(19)
_cell_measurement_reflns_used    4632
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.67
_cell_measurement_theta_min      2.22
_cell_volume                     1944.8(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            13219
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_max  0.9521
_exptl_absorpt_correction_T_min  0.9334
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2011)'
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4465
_refine_ls_number_restraints     172
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0342
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0184P)^2^+0.4486P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0659
_refine_ls_wR_factor_ref         0.0695
_reflns_number_gt                3793
_reflns_number_total             4465
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc02256h2.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P2(1)2(1)2(1) '
_cod_database_code               7117190