The regioselective synthesis of 2,5- and 4,5-disubstituted thiazoles <i>via</i> the cyclization of 2-oxo-2-(amino)ethanedithioates with isocyanides.
Ravi Singh, Krishna; Santhosh, Chikkappaiahnayaka; Swaroop, Toreshettahally R.; Sadashiva, Maralinganadoddi P.; Organic & biomolecular chemistry 20 (2022) 5771–5778; doi:10.1039/d2ob00837h

data_7158765
_publ_section_title
;
 The regioselective synthesis of 2,5- and 4,5-disubstituted thiazoles
 <i>via</i> the cyclization of 2-oxo-2-(amino)ethanedithioates with
 isocyanides.
;
_journal_issue                   29
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5771
_journal_page_last               5778
_journal_paper_doi               10.1039/d2ob00837h
_journal_volume                  20
_journal_year                    2022
_chemical_formula_sum            'C11 H9 Br N2 O S2'
_chemical_formula_weight         329.23
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-11-01 deposited with the CCDC.	2022-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                62.656(2)
_cell_angle_beta                 78.805(2)
_cell_angle_gamma                65.198(2)
_cell_formula_units_Z            4
_cell_length_a                   10.6549(6)
_cell_length_b                   11.8312(6)
_cell_length_c                   12.7053(7)
_cell_measurement_reflns_used    6367
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.273
_cell_measurement_theta_min      3.295
_cell_volume                     1291.45(12)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            46752
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.273
_diffrn_reflns_theta_min         3.295
_diffrn_standards_number         46752
_exptl_absorpt_coefficient_mu    3.490
_exptl_absorpt_correction_T_max  0.592
_exptl_absorpt_correction_T_min  0.503
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Crys Alis RED'
_exptl_crystal_colour            'clear whitish'
_exptl_crystal_density_diffrn    1.693
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.630
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         6367
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0402
_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^)+(0.0504P)^2^+1.1271P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1145
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4665
_reflns_number_total             6367
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00837h2.cif
_cod_data_source_block           4A-R1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7158765--7158766.cif.

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C22 H18 Br2 N4 O2 S4'
_cod_original_formula_weight         658.46
_cod_original_formula_units_Z            2
_cod_database_code               7158765
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.542
_shelx_estimated_absorpt_t_max   0.623
_shelx_res_checksum              95437