Cu-Catalyzed and iodine mediated synthesis of thioaurones via in situ C–S bond generation using xanthate as a sulfur surrogate
Soundarya, Palanisamy; Sekar, Govindasamy; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01211A

data_7158882
_publ_section_title
;
 Cu-Catalyzed and iodine mediated synthesis of thioaurones via in situ
 C--S bond generation using xanthate as a sulfur surrogate
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01211A
_journal_year                    2022
_chemical_formula_sum            'C15 H9 Cl O S'
_chemical_formula_weight         272.73
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc29xgl9
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2022-01-17 deposited with the CCDC.	2022-09-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.455(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.345(3)
_cell_length_b                   3.9444(5)
_cell_length_c                   14.7541(19)
_cell_measurement_reflns_used    1970
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.73
_cell_measurement_theta_min      2.81
_cell_volume                     1221.6(3)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3475
_diffrn_reflns_point_group_measured_fraction_full 0.808
_diffrn_reflns_point_group_measured_fraction_max 0.808
_diffrn_reflns_theta_full        24.989
_diffrn_reflns_theta_max         24.989
_diffrn_reflns_theta_min         1.940
_exptl_absorpt_coefficient_mu    0.465
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_description       Rectangular
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
; 
 Flack x determined using 612 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.92(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1747
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0278
_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^)+(0.0198P)^2^+0.6737P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0582
_refine_ls_wR_factor_ref         0.0614
_reflns_Friedel_coverage         0.665
_reflns_Friedel_fraction_full    0.646
_reflns_Friedel_fraction_max     0.646
_reflns_number_gt                1614
_reflns_number_total             1747
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01211a2.cif
_cod_data_source_block           113
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7158882
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.893
_shelx_estimated_absorpt_t_max   0.933
_shelx_res_checksum              41564
_shelx_hkl_checksum              52499