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_7130513
_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 O3 S'
_chemical_formula_sum            'C23 H20 F N O3 S'
_chemical_formula_weight         409.49
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-01-07 deposited with the CCDC.	2022-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.615(2)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   18.3227(8)
_cell_length_b                   6.1273(3)
_cell_length_c                   54.463(2)
_cell_measurement_reflns_used    9273
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.27
_cell_measurement_theta_min      3.25
_cell_volume                     6108.1(5)
_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 0.982
_diffrn_measured_fraction_theta_max 0.980
_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  0.1043
_diffrn_reflns_av_unetI/netI     0.1094
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       65
_diffrn_reflns_limit_l_min       -65
_diffrn_reflns_number            61872
_diffrn_reflns_point_group_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.377
_diffrn_reflns_theta_min         2.414
_exptl_absorpt_coefficient_mu    1.696
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.4914
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       rod
_exptl_crystal_F_000             2568
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: EA, Hexane'
_exptl_crystal_size_max          0.777
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.650
_refine_diff_density_min         -0.564
_refine_diff_density_rms         0.127
_refine_ls_abs_structure_details
; 
 Flack x determined using 4927 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.031(11)
_refine_ls_extinction_coef       0.00193(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1604
_refine_ls_number_reflns         21322
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1171
_refine_ls_R_factor_gt           0.0816
_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^)+(0.1087P)^2^+1.0901P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1774
_refine_ls_wR_factor_ref         0.2070
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_full    0.916
_reflns_Friedel_fraction_max     0.910
_reflns_number_gt                15316
_reflns_number_total             21322
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc03443c2.cif
_cod_data_source_block           lzj020
_cod_depositor_comments
;

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C138 H120 F6 N6 O18 S6'
_cod_original_formula_weight         2456.75
_cod_original_formula_moiety         '6(C23 H20 F N O3 S)'
_cod_original_formula_units_Z            2
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7130513
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.352
_shelx_estimated_absorpt_t_max   0.862
_shelx_res_checksum              24784
_shelx_hkl_checksum              47884