Iodine-enabled organoelectrocatalysis: enantioselective cross dehydrogenative coupling of sulfides and aldehydes
Wang, Zhen; Gausmann, Marcel; Dickoff, Jan-Hendrik; Christmann, Mathias; Green Chemistry 26 (2024) 2546–2551; doi:10.1039/D3GC03828A

data_7248181
_publ_section_title
;
 Iodine-enabled organoelectrocatalysis: enantioselective cross
 dehydrogenative coupling of sulfides and aldehydes
;
_journal_issue                   5
_journal_name_full               'Green Chemistry'
_journal_page_first              2546
_journal_page_last               2551
_journal_paper_doi               10.1039/D3GC03828A
_journal_volume                  26
_journal_year                    2024
_chemical_absolute_configuration rm
_chemical_formula_sum            'C22 H24 N2 O6 S'
_chemical_formula_weight         444.49
_chemical_name_systematic
'(R)-2-cyclohexyl-2-(p-tolylthio)ethyl 3,5-dinitrobenzoate'
_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
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2023-05-18 deposited with the CCDC.	2024-02-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.4062(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.34031(9)
_cell_length_b                   7.13358(5)
_cell_length_c                   24.66536(18)
_cell_measurement_reflns_used    9212
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.16
_cell_measurement_theta_min      3.65
_cell_volume                     2128.42(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker Photon CMOS Detector, D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            34981
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.209
_diffrn_reflns_theta_min         3.654
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    1.716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1634 before and 0.1073 after correction.
The Ratio of minimum to maximum transmission is 0.5908.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       rod
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.590
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_exptl_transmission_factor_max   0.7531
_exptl_transmission_factor_min   0.4449
_refine_diff_density_max         0.695
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.174
_refine_ls_abs_structure_details
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     561
_refine_ls_number_reflns         7622
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0552
_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^)+(0.0774P)^2^+0.4244P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1244
_reflns_Friedel_coverage         0.850
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                7315
_reflns_number_total             7622
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc03828a2.cif
_cod_data_source_block           ZW_CH119
_cod_depositor_comments          'Adding full bibliography for 7248181.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7248181
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.431
_shelx_estimated_absorpt_t_max   0.919
_shelx_res_checksum              7866
_shelx_hkl_checksum              80619