Asymmetric organocatalytic sulfenylation for the construction of a diheteroatom-bearing tetrasubstituted carbon centre
Tan, Qingfa; Chen, Qianping; Zhu, Zitong; Liu, Xiaohua; Chemical Communications  (2022) –; doi:10.1039/D2CC03443C

data_7130514
_publ_section_title
;
 Asymmetric organocatalytic sulfenylation for the construction of a
 diheteroatom-bearing tetrasubstituted carbon centre
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC03443C
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H20 F N O2 S'
_chemical_formula_sum            'C23 H20 F N O2 S'
_chemical_formula_weight         393.46
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-03-02 deposited with the CCDC.	2022-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.1960(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.7902(2)
_cell_length_b                   8.5037(2)
_cell_length_c                   11.6291(3)
_cell_measurement_reflns_used    9984
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.24
_cell_measurement_theta_min      3.81
_cell_volume                     966.65(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12024
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.272
_diffrn_reflns_theta_min         3.807
_exptl_absorpt_coefficient_mu    1.723
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6527
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_description       flake
_exptl_crystal_F_000             412
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM, PE'
_exptl_crystal_size_max          0.327
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_min          0.022
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
; 
 Flack x determined using 1504 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.040(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3461
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0284
_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=1/[\s^2^(Fo^2^)+(0.0400P)^2^+0.0913P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0716
_refine_ls_wR_factor_ref         0.0728
_reflns_Friedel_coverage         0.840
_reflns_Friedel_fraction_full    0.963
_reflns_Friedel_fraction_max     0.960
_reflns_number_gt                3370
_reflns_number_total             3461
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc03443c2.cif
_cod_data_source_block           tqf012
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7130514
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.603
_shelx_estimated_absorpt_t_max   0.963
_shelx_res_checksum              50010
_shelx_hkl_checksum              19855