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_2312108
_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_absolute_configuration ad
_chemical_formula_moiety         'C12 H13 N3 O2 S'
_chemical_formula_sum            'C12 H13 N3 O2 S'
_chemical_formula_weight         263.31
_chemical_melting_point_gt       517
_chemical_melting_point_lt       518
_chemical_name_systematic
;
5-dimethylaminomethylidene-4-(2-hydroxyphenyl)amino-1,3-thiazol-2(5H)-one
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-05-03 # Formatted by IUCr publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   46.689(4)
_cell_length_b                   12.2502(6)
_cell_length_c                   8.2435(4)
_cell_measurement_reflns_used    6185
_cell_measurement_temperature    130.0(1)
_cell_measurement_theta_max      75.95
_cell_measurement_theta_min      3.72
_cell_volume                     4714.9(5)
_computing_cell_refinement       'CrysAlisPro 1.171.37.35  (Rigaku OD, 2014)'
_computing_data_collection       'CrysAlisPro 1.171.37.35  (Rigaku OD, 2014)'
_computing_data_reduction        'CrysAlisPro 1.171.37.35  (Rigaku OD, 2014)'
_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 5.1996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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  0.0371
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       58
_diffrn_reflns_limit_h_min       -57
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12261
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         76.284
_diffrn_reflns_theta_min         3.787
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.438
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39495
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.37.35 (Rigaku Oxford Diffraction, 2014)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_description       plate
_exptl_crystal_F_000             2208
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 950 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2358
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0279
_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^)+(0.0341P)^2^+5.7549P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0684
_refine_ls_wR_factor_ref         0.0700
_reflns_Friedel_coverage         0.778
_reflns_Friedel_fraction_full    0.923
_reflns_Friedel_fraction_max     0.895
_reflns_number_gt                2257
_reflns_number_total             2358
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lo5112sup1.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 2312108--2312110.cif.'
_cod_database_code               2312108
_cod_database_fobs_code          2312108
_publcif_datablock.id            {dcc6f9c9-fec6-4412-ba50-529feec04f56}
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              53823
_shelx_hkl_checksum              73441