Base-promoted regioselective synthesis of alkyl (2-tosyl/4-ethylcarbonyl) thiazole-5-carboxylates employing dithioates and active methylene isocyanides
Santhosh, Chikkappaiahnayaka; Singh, Krishna Ravi; Mane, Manoj V.; Sheela, Kalleshappa; Sharath, Kalleshappa; Sadashiva, Maralinganadoddi P.; New Journal of Chemistry 49 (2025) 4604–4614; doi:10.1039/D4NJ04515G

data_7063665
_publ_section_title
;
 Base-promoted regioselective synthesis of alkyl (2-tosyl/4-ethylcarbonyl)
 thiazole-5-carboxylates employing dithioates and active methylene
 isocyanides
;
_journal_issue                   11
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              4604
_journal_page_last               4614
_journal_paper_doi               10.1039/D4NJ04515G
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         'C14 H12 Cl N O4 S'
_chemical_formula_sum            'C14 H12 Cl N O4 S'
_chemical_formula_weight         329.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/2
_audit_update_record
;
2024-01-08 deposited with the CCDC.	2025-02-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.898(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7650(7)
_cell_length_b                   7.5431(4)
_cell_length_c                   15.3707(9)
_cell_measurement_reflns_used    3673
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      2.743
_cell_volume                     1542.30(15)
_computing_cell_refinement       'SAINT/ XPREP (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT/ XPREP (Bruker, 2016)'
_computing_molecular_graphics    Mercury
_computing_publication_material  Platon
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 VENTURE difractometer'
_diffrn_measurement_method       '\w and \f scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            51308
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.884
_diffrn_reflns_theta_min         2.743
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.396
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.456
_exptl_crystal_size_mid          0.363
_exptl_crystal_size_min          0.232
_exptl_transmission_factor_max   0.912
_exptl_transmission_factor_min   0.840
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3673
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0634
_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^)+(0.0940P)^2^+1.3544P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1764
_refine_ls_wR_factor_ref         0.2114
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2873
_reflns_number_total             3673
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj04515g2.cif
_cod_data_source_block           e5
_cod_depositor_comments
'Adding full bibliography for 7063664--7063665.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7063665
_shelx_shelxl_version_number     2019/2
_shelx_res_checksum              94651
_shelx_hkl_checksum              92618