Pd/PTABS: Low-Temperature Thioetherification of Chloro(hetero)arenes.
Bandaru, Siva Sankar Murthy; Bhilare, Shatrughn; Cardozo, Jesvita; Chrysochos, Nicolas; Schulzke, Carola; Sanghvi, Yogesh S.; Gunturu, Krishna Chaitanya; Kapdi, Anant R.; The Journal of organic chemistry 84 (2019) 8921–8940; doi:10.1021/acs.joc.9b00840

data_4034194
_publ_section_title
;
 Pd/PTABS: Low-Temperature Thioetherification of Chloro(hetero)arenes.
;
_journal_issue                   14
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8921
_journal_page_last               8940
_journal_paper_doi               10.1021/acs.joc.9b00840
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C14 H10 N2 S'
_chemical_formula_sum            'C14 H10 N2 S'
_chemical_formula_weight         238.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.601(3)
_cell_length_b                   12.379(3)
_cell_length_c                   5.5695(11)
_cell_measurement_reflns_used    13277
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.46
_cell_measurement_theta_min      2.29
_cell_volume                     1144.6(4)
_computing_cell_refinement       'X-Area by STOE & Cie GmbH 2010'
_computing_data_collection       'X-Area by STOE & Cie GmbH 2010'
_computing_data_reduction        'X-Area by STOE & Cie GmbH 2010'
_computing_molecular_graphics    'XP Version 5.1 by Bruker AXS 1998'
_computing_publication_material  'CIFTAB (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2018 (Sheldrick, 2015)'
_diffrn_ambient_temperature      170(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'STOE IPDS2T'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            12817
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.461
_diffrn_reflns_theta_min         3.513
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       stick
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.289
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.069
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Flack x determined using 915 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3138
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0402
_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^)+(0.0356P)^2^+0.5171P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.1031
_reflns_Friedel_coverage         0.807
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                2465
_reflns_number_total             3138
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00840_si_001.cif
_cod_data_source_block           SIV-01-359
_cod_original_cell_volume        1144.5(4)
_cod_database_code               4034194
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.929
_shelx_estimated_absorpt_t_max   0.982
_shelx_res_checksum              24139
_shelx_hkl_checksum              4257