A one-pot route to thioamides discovered by gas-phase studies: palladium-mediated CO2 extrusion followed by insertion of isothiocyanates.
Noor, Asif; Li, Jiawei; Khairallah, George N.; Li, Zhen; Ghari, Hossein; Canty, Allan J.; Ariafard, Alireza; Donnelly, Paul S.; O'Hair, Richard A J; Chemical communications (Cambridge, England) 53 (2017) 3854–3857; doi:10.1039/c7cc00865a

data_7119802
_publ_section_title
;
 A one-pot route to thioamides discovered by gas-phase studies:
 palladium-mediated CO2 extrusion followed by insertion of
 isothiocyanates.
;
_journal_issue                   27
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3854
_journal_page_last               3857
_journal_paper_doi               10.1039/c7cc00865a
_journal_volume                  53
_journal_year                    2017
_chemical_formula_sum            'C16 H14 F3 N O2 S'
_chemical_formula_weight         341.34
_chemical_name_systematic
2,6-dimethoxy-N-(4-(trifluoromethyl)phenyl)benzothioamide
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-03-16 deposited with the CCDC.
2017-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.543(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2091(2)
_cell_length_b                   7.59230(10)
_cell_length_c                   18.4855(3)
_cell_measurement_reflns_used    8004
_cell_measurement_temperature    130.00(10)
_cell_measurement_theta_max      76.1590
_cell_measurement_theta_min      3.9550
_cell_volume                     1573.10(4)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      130.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14080
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.906
_diffrn_reflns_theta_min         4.594
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.210
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.492
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.226
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3294
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.925
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0327
_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^)+(0.0513P)^2^+0.8479P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0874
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3099
_reflns_number_total             3294
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc00865a2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7119797--7119802.cif.'
_cod_database_code               7119802
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              85355
_solvent_exptl_crystal_recrystallization_method
'Slow evaporation of dichloromethane and pentane mixtures'