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_7158766
_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_moiety         'C13 H11 Br N2 O3 S'
_chemical_formula_sum            'C13 H11 Br N2 O3 S'
_chemical_formula_weight         355.21
_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_date             2021-09-26
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c4697 for OlexSys, GUI svn.r6394)
;
_audit_update_record
;
2021-11-01 deposited with the CCDC.	2022-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.190(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5681(4)
_cell_length_b                   14.0924(9)
_cell_length_c                   15.4674(10)
_cell_measurement_reflns_used    9895
_cell_measurement_temperature    297.00
_cell_measurement_theta_max      70.17
_cell_measurement_theta_min      4.25
_cell_volume                     1427.84(16)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      297.00
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type
'Bruker D8 VENTURE diffractometer with PHOTON II detector'
_diffrn_measurement_method       '\w and \f scan'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23502
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.436
_diffrn_reflns_theta_min         4.249
_exptl_absorpt_coefficient_mu    5.380
_exptl_absorpt_correction_T_max  0.6617
_exptl_absorpt_correction_T_min  0.2288
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1534 before and 0.0921 after correction.
The Ratio of minimum to maximum transmission is 0.3458.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.947
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.330
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2689
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.330
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0686
_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^)+5.7894P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1507
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2295
_reflns_number_total             2689
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00837h2.cif
_cod_data_source_block           4b
_cod_depositor_comments
'Adding full bibliography for 7158765--7158766.cif.'
_cod_database_code               7158766
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.499
_shelx_estimated_absorpt_t_min   0.413
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 N8(H8), C6(H6), C7(H7), C4(H4), C3(H3), C13(H13)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_shelx_res_checksum              85498
_olex2_submission_special_instructions 'No special instructions were received'