Reaction of unsymmetrical α-bromo-1,3-diketones with N-substituted thioureas: regioselective access to 2-(N-arylamino)-5-acyl-4-methylthiazoles and/or rearranged 2-(N-acylimino)-3-N-aryl-4-methylthiazoles
Aggarwal, Ranjana; Sharma, Shilpa; Jain, Naman; Sanz, Dionisia; Claramunt, Rosa M.; Delgado, Patricia; Torralba, M. Carmen; RSC Advances 14 (2024) 35585–35600; doi:10.1039/D4RA05436A

data_7249562
_publ_section_title
;
 Reaction of unsymmetrical \a-bromo-1,3-diketones with N-substituted
 thioureas: regioselective access to
 2-(N-arylamino)-5-acyl-4-methylthiazoles and/or rearranged
 2-(N-acylimino)-3-N-aryl-4-methylthiazoles
;
_journal_issue                   48
_journal_name_full               'RSC Advances'
_journal_page_first              35585
_journal_page_last               35600
_journal_paper_doi               10.1039/D4RA05436A
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C18 H15 Cl N2 O2 S'
_chemical_formula_sum            'C18 H15 Cl N2 O2 S'
_chemical_formula_weight         358.83
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2023-12-04
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-12-05 deposited with the CCDC.	2024-08-29 downloaded from the CCDC.
;
_cell_angle_alpha                107.810(2)
_cell_angle_beta                 110.578(2)
_cell_angle_gamma                96.950(2)
_cell_formula_units_Z            2
_cell_length_a                   9.4627(10)
_cell_length_b                   9.6608(10)
_cell_length_c                   11.0027(11)
_cell_measurement_reflns_used    2344
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      23.9914
_cell_measurement_theta_min      2.2908
_cell_volume                     866.57(16)
_computing_cell_refinement       'SAINT v6.28A (Bruker, 2002)'
_computing_data_reduction        'SAINT v6.28A (Bruker, 2002)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.892
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9152
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.090
_diffrn_reflns_theta_min         2.133
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.353
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.844934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) was 0.0442 before and 0.0203 after correction. The Ratio of minimum to maximum transmission is 0.8449. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         4133
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.970
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0580P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1292
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2063
_reflns_number_total             4133
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra05436a2.cif
_cod_data_source_block           data1t
_cod_database_code               7249562
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C9(H9), C10(H10), C12(H12), C13(H13), C15(H15), C16(H16), C18(H18),
 C19(H19)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              25036
_shelx_hkl_checksum              4107
_olex2_submission_original_sample_id 'sph 53b'
_olex2_submission_special_instructions 'No special instructions were received'