Proton tautomerism and stereoisomerism in 5-[(dimethylamino)methylidene]-4-[3/4-(trifluoromethylphenyl)amino]-1,3-thiazol-2(5H)-ones: synthesis, crystal structure and spectroscopic studies.
Pyrih, Andrii; Łapiński, Andrzej; Zięba, Sylwia; Mizera, Adam; Lesyk, Roman; Gzella, Andrzej K.; Jaskolski, Mariusz; Acta crystallographica. Section C, Structural chemistry 79 (2023) –; doi:10.1107/S2053229623009087

data_2312322
_publ_section_title
;
 Proton tautomerism and stereoisomerism in
 5-[(dimethylamino)methylidene]-4-[3/4-(trifluoromethylphenyl)amino]-1,3-thiazol-2(5H)-ones:
 synthesis, crystal structure and spectroscopic studies.
;
_journal_coeditor_code           OJ3012
_journal_issue                   11
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_paper_doi               10.1107/S2053229623009087
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C13 H12 F3 N3 O S'
_chemical_formula_moiety         'C13 H12 F3 N3 O S'
_chemical_formula_sum            'C13 H12 F3 N3 O S'
_chemical_formula_weight         315.32
_chemical_melting_point_gt       579
_chemical_melting_point_lt       580
_chemical_name_systematic
5-[(Dimethylamino)methylidene]-4-{[4-(trifluoromethyl)phenyl]amino}-1,3-thiazol-2(5<i>H</i>)-one
_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'
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_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_cell_angle_beta                 90.123(4)
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_cell_length_c                   7.6297(3)
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_cell_measurement_temperature    130(2)
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_cell_measurement_theta_min      3.10
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_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2019)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2019)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2019)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
WinGX (Farrugia, 2012),
OLEX2 (Dolomanov <i>et al.</i>,  2009) and
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015<i>b</i>)
;
_computing_structure_solution
;
SHELXT2018 (Sheldrick, 2015<i>a</i>)
;
_diffrn_ambient_temperature      130.00(10)
_diffrn_detector_area_resol_mean 10.3991
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type
'Rigaku OD SuperNova Dual source diffractometer with an Atlas detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0394
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_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
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_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.329
_diffrn_reflns_theta_min         3.163
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;
(CrysAlis PRO; Rigaku OD, 2014)
;
_exptl_crystal_colour            Yellow
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_exptl_crystal_size_min          0.04
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_refine_diff_density_min         -0.345
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_refine_ls_number_reflns         2713
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0548
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_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^)+(0.0544P)^2^+2.4271P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_refine_ls_wR_factor_ref         0.1414
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_reflns_threshold_expression     'I > 2\s(I)'
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_cod_data_source_block           5
_cod_original_cell_volume        1316.20(9)
_cod_original_sg_symbol_H-M      'P 21/c'
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_cod_database_fobs_code 2312322