Optically Pure Polyfluoroalkanesulfinamides: Synthesis and Application as Promising and Monitorable Chiral Auxiliaries
Li-Juan Liu; Ling-Jun Chen; Peng Li; Xiao-Bo Li; Jin-Tao Liu; Journal of Organic Chemistry 76 (2011) 4675–4681; doi:10.1021/jo200119x

data_4026350
_publ_section_title
;
 Optically Pure Polyfluoroalkanesulfinamides: Synthesis and Application as
 Promising and Monitorable Chiral Auxiliaries
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4675
_journal_page_last               4681
_journal_paper_doi               10.1021/jo200119x
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_sum            'C12 H10 Cl F4 N O3 S'
_chemical_formula_weight         359.72
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.213(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   25.200(5)
_cell_length_b                   5.6924(11)
_cell_length_c                   11.547(2)
_cell_measurement_reflns_used    1685
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      47.541
_cell_measurement_theta_min      5.034
_cell_volume                     1590.5(5)
_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-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.1379
_diffrn_reflns_av_sigmaI/netI    0.0944
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4180
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.422
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65123
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.503
_exptl_crystal_size_mid          0.317
_exptl_crystal_size_min          0.062
_refine_diff_density_max         0.603
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -10(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         1628
_refine_ls_number_restraints     44
_refine_ls_restrained_S_all      1.144
_refine_ls_R_factor_all          0.0913
_refine_ls_R_factor_gt           0.0843
_refine_ls_shift/su_max          0.059
_refine_ls_shift/su_mean         0.010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1605P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2141
_refine_ls_wR_factor_ref         0.2250
_reflns_number_gt                1389
_reflns_number_total             1628
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200119x_si_002.cif
_cod_data_source_block           cd27169
_cod_original_cell_volume        1590.6(5)
_cod_database_code               4026350