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_4034195
_publ_section_title
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 Pd/PTABS: Low-Temperature Thioetherification of Chloro(hetero)arenes.
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_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         'C11 H8 N4 S'
_chemical_formula_sum            'C11 H8 N4 S'
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_space_group_crystal_system      monoclinic
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_cell_angle_beta                 93.19(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_b                   7.1958(14)
_cell_length_c                   12.597(3)
_cell_measurement_reflns_used    11247
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      58.9
_cell_measurement_theta_min      6.5
_cell_volume                     1005.8(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'
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_computing_structure_solution    'SHELXT-2016/3(Sheldrick, 2015)'
_diffrn_ambient_temperature      170(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_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  0.0393
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10884
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.422
_diffrn_reflns_theta_min         3.262
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.295
_exptl_absorpt_correction_T_max  0.9936
_exptl_absorpt_correction_T_min  0.8383
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'face indexed'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.465
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_exptl_crystal_size_min          0.145
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_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2766
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0316
_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^)+(0.0496P)^2^+0.3264P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0884
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2480
_reflns_number_total             2766
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00840_si_003.cif
_cod_data_source_block           SIV-01-361
_cod_original_cell_volume        1005.8(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4034195
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.875
_shelx_estimated_absorpt_t_max   0.958
_exptl_absorpt_special_details
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programs X-Red32 and X-Shape by STOE & Cie GmbH 2010
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_shelx_res_checksum              80839
_shelx_hkl_checksum              1686