Catalytic I<sub>2</sub>-moist DMSO-mediated synthesis of valuable α-amidohydroxyketones and unsymmetrical <i>gem</i>-bisamides from benzimidates.
Aich, Shobhon; Nandi, Rajesh; Chatterjee, Nirbhik; Gayen, Krishnanka S.; Pal, Subhasis; Maiti, Dilip K.; Organic & biomolecular chemistry 21 (2023) 2524–2530; doi:10.1039/d3ob00165b

data_7159150
_publ_section_title
;
 Catalytic I<sub>2</sub>-moist DMSO-mediated synthesis of valuable
 &#x3b1;-amidohydroxyketones and unsymmetrical <i>gem</i>-bisamides from
 benzimidates.
;
_journal_issue                   12
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2524
_journal_page_last               2530
_journal_paper_doi               10.1039/d3ob00165b
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C13 H11 N O3 S'
_chemical_formula_sum            'C13 H11 N O3 S'
_chemical_formula_weight         261.29
_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-2016/6
_audit_update_record
;
2022-02-17 deposited with the CCDC.	2023-02-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.955(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.107(4)
_cell_length_b                   24.81(2)
_cell_length_c                   9.865(8)
_cell_measurement_reflns_used    18299
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.995
_cell_measurement_theta_min      1.642
_cell_volume                     1248.3(17)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Apex II'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1588
_diffrn_reflns_av_unetI/netI     0.1445
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            18299
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         1.642
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_correction_T_min  0.907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.098
_refine_ls_abs_structure_details
;
 Flack x determined using 675 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.42(14)
_refine_ls_extinction_coef       0.054(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         4346
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1834
_refine_ls_R_factor_gt           0.0829
_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^)+(0.1052P)^2^+0.1091P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1819
_refine_ls_wR_factor_ref         0.2395
_reflns_Friedel_coverage         0.934
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                2053
_reflns_number_total             4346
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00165b2.cif
_cod_data_source_block           SA84
_cod_depositor_comments          'Adding full bibliography for 7159150.cif.'
_cod_original_cell_volume        1248.2(17)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7159150
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              24129