Lewis Acid-Catalyzed Asymmetric Selenocyanation of β-Ketoesters with N-Selenocyanatosaccharin.
Wu, Di; Qiu, Jiashen; Li, Chengqiu; Yuan, Lexia; Yin, Hongquan; Chen, Fu-Xue; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02786

data_4037722
_publ_section_title
;
 Lewis Acid-Catalyzed Asymmetric Selenocyanation of \b-Ketoesters with
 N-Selenocyanatosaccharin.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02786
_journal_year                    2019
_chemical_absolute_configuration S
_chemical_formula_sum            'C22 H23 N O3 Se'
_chemical_formula_weight         428.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.484(2)
_cell_length_b                   15.984(3)
_cell_length_c                   20.269(3)
_cell_measurement_reflns_used    8242
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.53
_cell_measurement_theta_min      2.30
_cell_volume                     4044.6(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.948
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.948
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            38362
_diffrn_reflns_point_group_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.801
_diffrn_reflns_theta_min         1.622
_exptl_absorpt_coefficient_mu    1.878
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_description       needle
_exptl_crystal_F_000             1760
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
; 
 Flack x determined using 1701 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.009(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     487
_refine_ls_number_reflns         6914
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.965
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0437
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0470P)^2^+1.8723P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1131
_reflns_Friedel_coverage         0.786
_reflns_Friedel_fraction_full    0.941
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                4752
_reflns_number_total             6914
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02786_si_002.cif
_cod_data_source_block           wd-0589-1
_cod_database_code               4037722
_shelxl_version_number           2014-3
_shelx_res_checksum              93598
_shelx_hkl_checksum              87467