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_7119797
_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            'C10 H13 N O2 S'
_chemical_formula_weight         211.27
_chemical_name_systematic        2,6-dimethoxy-N-methylbenzothioamide
_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'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.1567(2)
_cell_length_b                   8.34180(10)
_cell_length_c                   8.61660(10)
_cell_measurement_reflns_used    7167
_cell_measurement_temperature    130.00(10)
_cell_measurement_theta_max      76.9920
_cell_measurement_theta_min      6.0520
_cell_volume                     1089.43(2)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      130.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_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  0.0248
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8872
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.001
_diffrn_reflns_theta_min         6.055
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.445
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57275
_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            colorless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_description       Block
_exptl_crystal_F_000             448
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.723
_exptl_crystal_size_mid          0.431
_exptl_crystal_size_min          0.358
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 983 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2220
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0252
_refine_ls_R_factor_gt           0.0251
_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^)+(0.0523P)^2^+0.0311P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0658
_refine_ls_wR_factor_ref         0.0659
_reflns_Friedel_coverage         0.820
_reflns_Friedel_fraction_full    0.959
_reflns_Friedel_fraction_max     0.933
_reflns_number_gt                2209
_reflns_number_total             2220
_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               7119797
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              14653
_solvent_exptl_crystal_recrystallization_method
'Slow evaporation of dichloromethane and pentane mixtures'