Proton tautomerism in 5-dimethylaminomethylidene-4-(o-,m-,p-hydroxyphenyl)amino-1,3-thiazol-2(5H)-ones: synthesis, crystal structure and spectroscopic studies.
Pyrih, Andrii; Łapiński, Andrzej; Zięba, Sylwia; Mizera, Adam; Lesyk, Roman; Jaskolski, Mariusz; Gzella, Andrzej K.; Acta crystallographica Section B, Structural science, crystal engineering and materials 79 (2023) 220–232; doi:10.1107/S2052520623003852

data_2312109
_publ_section_title
;
 Proton tautomerism in
 5-dimethylaminomethylidene-4-(o-,m-,p-hydroxyphenyl)amino-1,3-thiazol-2(5H)-ones:
 synthesis, crystal structure and spectroscopic studies.
;
_journal_issue                   3
_journal_name_full
'Acta crystallographica Section B, Structural science, crystal engineering and materials'
_journal_page_first              220
_journal_page_last               232
_journal_paper_doi               10.1107/S2052520623003852
_journal_volume                  79
_journal_year                    2023
_chemical_formula_moiety         'C12 H13 N3 O2 S, C3 H7 N O'
_chemical_formula_sum            'C15 H20 N4 O3 S'
_chemical_formula_weight         336.41
_chemical_melting_point_gt       492
_chemical_melting_point_lt       493
_chemical_name_systematic
;
5-dimethylaminomethylidene-4-(3-hydroxyphenyl)amino-1,3-thiazol-2(5H)-one 
dimethylformamide solvate
;
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 104.534(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.7594(3)
_cell_length_b                   11.8833(2)
_cell_length_c                   13.3407(2)
_cell_measurement_reflns_used    9527
_cell_measurement_temperature    130.0(1)
_cell_measurement_theta_max      76.19
_cell_measurement_theta_min      5.11
_cell_volume                     3185.70(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material
; 
WINGX (Farrugia, 2012), OLEX2 v1.2-alpha (Dolomanov et al., 2009), 
PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      130.0(1)
_diffrn_detector_area_resol_mean 10.3991
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'SuperNova, Dual, Cu, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11361
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.517
_diffrn_reflns_theta_min         2.199
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.993
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_description       lath
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     440
_refine_ls_number_reflns         11361
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0415
_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^)+(0.0911P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1271
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9171
_reflns_number_total             11361
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by -179.9932\% 
 around [-0.36 0.00 0.93] (reciprocal) or [-0.00 0.00 1.00] (direct)
;
_cod_data_source_file            lo5112sup1.cif
_cod_data_source_block           2.DMF
_cod_depositor_comments
'Adding full bibliography for 2312108--2312110.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2312109
_cod_database_fobs_code          2312109
_publcif_datablock.id            {07190ad9-2b14-469b-90b9-f570843d1fff}
_shelx_shelxl_version_number     2018/3
_oxdiff_twin_items               2
_oxdiff_twin_integration_method  simultaneous
_shelx_res_checksum              86229
_shelx_hkl_checksum              27048