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_7130515
_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         '4(C22 H19 N O3 S)'
_chemical_formula_sum            'C88 H76 N4 O12 S4'
_chemical_formula_weight         1509.76
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_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                72.846(2)
_cell_angle_beta                 79.748(2)
_cell_angle_gamma                68.951(2)
_cell_formula_units_Z            1
_cell_length_a                   11.3514(3)
_cell_length_b                   13.3056(4)
_cell_length_c                   14.4521(4)
_cell_measurement_reflns_used    9874
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.20
_cell_measurement_theta_min      3.21
_cell_volume                     1940.17(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            44996
_diffrn_reflns_point_group_measured_fraction_full 0.931
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.413
_diffrn_reflns_theta_min         3.211
_exptl_absorpt_coefficient_mu    1.659
_exptl_absorpt_correction_T_max  0.8787
_exptl_absorpt_correction_T_min  0.7091
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM, PE'
_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.117
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
; 
 Flack x determined using 5384 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.058(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1017
_refine_ls_number_reflns         13203
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0359
_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^)+(0.0153P)^2^+0.6285P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0751
_refine_ls_wR_factor_ref         0.0787
_reflns_Friedel_coverage         0.920
_reflns_Friedel_fraction_full    0.894
_reflns_Friedel_fraction_max     0.889
_reflns_number_gt                12237
_reflns_number_total             13203
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc03443c2.cif
_cod_data_source_block           tqf011
_cod_database_code               7130515
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.710
_shelx_estimated_absorpt_t_max   0.830
_shelx_res_checksum              18561
_shelx_hkl_checksum              62337