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_2312110
_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       553
_chemical_melting_point_lt       554
_chemical_name_systematic
;
5-dimethylaminomethylidene-4-(4-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                 99.213(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1630(2)
_cell_length_b                   17.0311(3)
_cell_length_c                   7.32120(10)
_cell_measurement_reflns_used    8581
_cell_measurement_temperature    130.0(1)
_cell_measurement_theta_max      75.95
_cell_measurement_theta_min      3.34
_cell_volume                     1620.10(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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 1.000
_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_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            17034
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.624
_diffrn_reflns_theta_max         76.397
_diffrn_reflns_theta_min         3.400
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.959
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_description       rod
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3380
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0324
_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^)+(0.0473P)^2^+0.6126P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0872
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3123
_reflns_number_total             3380
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lo5112sup1.cif
_cod_data_source_block           3.DMF
_cod_depositor_comments
'Adding full bibliography for 2312108--2312110.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2312110
_cod_database_fobs_code          2312110
_publcif_datablock.id            {bf37af0b-70f8-4480-adbc-dd6d2679c28d}
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              91453
_shelx_hkl_checksum              30182
_publcif_info_exptl_table_max_cols 5
_publcif_info_exptl_table_use_headnotes n
_publcif_funding_html
'<span class="funder"><span class="fundref-name" data-id="501100004895">European Social Fund</span><span class="fundref-subname" data-id=""></span> (<span class="fundref-grant-group"><span class="fundref-grant-type">grant</span> No. <span class="fundref-grant-id">POWR.03.02.00-00-I020/17</span></span>); </span><span class="funder"><span class="fundref-name" data-id="501100015097">Interdyscyplinarne Centrum Modelowania Matematycznego i Komputerowego UW</span><span class="fundref-subname" data-id=""></span> (<span class="fundref-grant-group"><span class="fundref-grant-type">grant</span> No. <span class="fundref-grant-id">G53-7</span></span>); </span><span class="funder"><span class="fundref-name" data-id="501100001870">Fundacja na rzecz Nauki Polskiej</span><span class="fundref-subname" data-id=""></span> (<span class="fundref-grant-group"><span class="fundref-grant-type">award</span> No. <span class="fundref-grant-id">START 098.2022</span></span>).</span> '