#------------------------------------------------------------------------------
#$Date: 2023-10-25 05:08:58 +0300 (Wed, 25 Oct 2023) $
#$Revision: 287105 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/23/2312321.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2312321
loop_
_publ_author_name
'Pyrih, Andrii'
'Łapiński, Andrzej'
'Zięba, Sylwia'
'Mizera, Adam'
'Lesyk, Roman'
'Gzella, Andrzej K.'
'Jaskolski, Mariusz'
_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       559
_chemical_melting_point_lt       560
_chemical_name_systematic
5-[(Dimethylamino)methylidene]-4-{[3-(trifluoromethyl)phenyl]amino}-1,3-thiazol-2(5H)-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'
_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                 116.290(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2418(4)
_cell_length_b                   28.0107(9)
_cell_length_c                   7.3569(4)
_cell_measurement_reflns_used    4294
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      75.56
_cell_measurement_theta_min      3.06
_cell_volume                     1337.97(14)
_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 et al.,  2009) and
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018 (Sheldrick, 2015a)
;
_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 0.989
_diffrn_measurement_device_type
'Rigaku OD SuperNova Dual source diffractometer with an Atlas detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            13508
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.611
_diffrn_reflns_theta_min         3.155
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.530
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2019)
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_description       Lath
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.864
_refine_diff_density_min         -0.431
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2791
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0706
_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/[σ²(Fo²)+(0.0652P)²+3.7293P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1800
_refine_ls_wR_factor_ref         0.1855
_reflns_number_gt                2394
_reflns_number_total             2791
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            oj3012sup1.cif
_cod_data_source_block           4
_cod_original_cell_volume        1337.97(13)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2312321
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.20317(13) 0.20587(3) 0.78289(14) 0.0279(3) Uani d 1 . .
C C2 0.1148(6) 0.26559(13) 0.7805(5) 0.0282(7) Uani d 1 . .
N N3 0.2559(4) 0.29898(10) 0.7933(4) 0.0259(6) Uani d 1 . .
C C4 0.4286(5) 0.27883(12) 0.8040(5) 0.0231(7) Uani d 1 . .
C C5 0.4385(5) 0.22782(13) 0.8027(5) 0.0249(7) Uani d 1 . .
O O6 -0.0583(4) 0.27299(10) 0.7657(4) 0.0334(6) Uani d 1 . .
N N7 0.5877(5) 0.30630(11) 0.8152(5) 0.0265(6) Uani d 1 . .
H H7 0.681(6) 0.2919(14) 0.814(6) 0.019(10) Uiso d 1 . .
C C8 0.6037(5) 0.35617(13) 0.8143(5) 0.0258(7) Uani d 1 . .
C C9 0.4375(6) 0.38733(13) 0.7419(6) 0.0288(7) Uani d 1 . .
H H9 0.301186 0.375273 0.692730 0.035 Uiso calc 1 . .
C C10 0.4706(6) 0.43614(14) 0.7413(6) 0.0321(8) Uani d 1 . .
C C11 0.6677(7) 0.45493(14) 0.8140(7) 0.0386(9) Uani d 1 . .
H H11 0.688734 0.488424 0.814924 0.046 Uiso calc 1 . .
C C12 0.8335(7) 0.42364(15) 0.8852(7) 0.0424(10) Uani d 1 . .
H H12 0.969507 0.435896 0.935129 0.051 Uiso calc 1 . .
C C13 0.8034(6) 0.37506(14) 0.8845(6) 0.0349(8) Uani d 1 . .
H H13 0.918617 0.354156 0.931917 0.042 Uiso calc 1 . .
C C14 0.2886(7) 0.46839(15) 0.6575(8) 0.0446(10) Uani d 1 . .
F F1 0.1655(11) 0.4585(2) 0.4583(10) 0.068(2) Uani d 0.83(3) A 1
F F2 0.1645(14) 0.4623(4) 0.7462(16) 0.081(2) Uani d 0.83(3) A 1
F F3 0.3322(6) 0.51423(12) 0.6622(16) 0.0653(17) Uani d 0.83(3) A 1
F F1A 0.126(2) 0.4500(7) 0.502(4) 0.068(2) Uani d 0.17(3) A 2
F F2A 0.222(5) 0.4785(12) 0.798(3) 0.081(2) Uani d 0.17(3) A 2
F F3A 0.327(3) 0.5103(6) 0.597(5) 0.0653(17) Uani d 0.17(3) A 2
C C15 0.6101(5) 0.20169(12) 0.8306(5) 0.0249(7) Uani d 1 . .
H H15 0.731828 0.219736 0.863654 0.030 Uiso calc 1 . .
N N16 0.6294(5) 0.15483(11) 0.8178(5) 0.0295(7) Uani d 1 . .
C C17 0.8337(6) 0.13317(14) 0.8962(7) 0.0363(9) Uani d 1 . .
H H17A 0.938939 0.158186 0.949182 0.054 Uiso calc 1 . .
H H17B 0.847485 0.115992 0.786853 0.054 Uiso calc 1 . .
H H17C 0.851773 0.110809 1.005320 0.054 Uiso calc 1 . .
C C18 0.4564(6) 0.12176(13) 0.7366(6) 0.0350(8) Uani d 1 . .
H H18A 0.417567 0.112830 0.843838 0.053 Uiso calc 1 . .
H H18B 0.496089 0.093088 0.686066 0.053 Uiso calc 1 . .
H H18C 0.339142 0.137096 0.625277 0.053 Uiso calc 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 S1 C2 . . 90.18(17) ?
O6 C2 N3 . . 126.7(3) ?
O6 C2 S1 . . 120.4(3) ?
N3 C2 S1 . . 112.9(3) ?
C4 N3 C2 . . 111.6(3) ?
N3 C4 N7 . . 120.6(3) ?
N3 C4 C5 . . 117.9(3) ?
N7 C4 C5 . . 121.5(3) ?
C15 C5 C4 . . 125.1(3) ?
C15 C5 S1 . . 127.2(3) ?
C4 C5 S1 . . 107.5(2) ?
C4 N7 C8 . . 129.4(3) ?
C4 N7 H7 . . 115(3) ?
C8 N7 H7 . . 116(3) ?
C9 C8 N7 . . 124.7(3) ?
C9 C8 C13 . . 118.7(3) ?
N7 C8 C13 . . 116.6(3) ?
C8 C9 C10 . . 119.9(3) ?
C8 C9 H9 . . 120.1 ?
C10 C9 H9 . . 120.1 ?
C11 C10 C9 . . 121.5(4) ?
C11 C10 C14 . . 120.1(4) ?
C9 C10 C14 . . 118.4(3) ?
C10 C11 C12 . . 118.4(4) ?
C10 C11 H11 . . 120.8 ?
C12 C11 H11 . . 120.8 ?
C13 C12 C11 . . 120.9(4) ?
C13 C12 H12 . . 119.6 ?
C11 C12 H12 . . 119.6 ?
C12 C13 C8 . . 120.5(4) ?
C12 C13 H13 . . 119.7 ?
C8 C13 H13 . . 119.7 ?
F3A C14 F1A . . 106.9(8) ?
F3 C14 F2 . . 108.4(4) ?
F3A C14 F2A . . 105.8(8) ?
F1A C14 F2A . . 105.0(8) ?
F3 C14 F1 . . 105.1(4) ?
F2 C14 F1 . . 103.8(4) ?
F3 C14 C10 . . 115.0(4) ?
F3A C14 C10 . . 113.3(7) ?
F1A C14 C10 . . 114.0(8) ?
F2 C14 C10 . . 112.6(4) ?
F2A C14 C10 . . 111.2(8) ?
F1 C14 C10 . . 111.0(4) ?
N16 C15 C5 . . 129.2(3) ?
N16 C15 H15 . . 115.4 ?
C5 C15 H15 . . 115.4 ?
C15 N16 C18 . . 124.0(3) ?
C15 N16 C17 . . 120.2(3) ?
C18 N16 C17 . . 115.8(3) ?
N16 C17 H17A . . 109.5 ?
N16 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
N16 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
N16 C18 H18A . . 109.5 ?
N16 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
N16 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C5 . 1.756(4) ?
S1 C2 . 1.788(4) ?
C2 O6 . 1.227(4) ?
C2 N3 . 1.357(5) ?
N3 C4 . 1.342(4) ?
C4 N7 . 1.357(4) ?
C4 C5 . 1.431(5) ?
C5 C15 . 1.377(5) ?
N7 C8 . 1.402(5) ?
N7 H7 . 0.79(4) ?
C8 C9 . 1.388(5) ?
C8 C13 . 1.406(5) ?
C9 C10 . 1.389(5) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.387(6) ?
C10 C14 . 1.488(6) ?
C11 C12 . 1.388(6) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.378(6) ?
C12 H12 . 0.9500 ?
C13 H13 . 0.9500 ?
C14 F3 . 1.319(5) ?
C14 F3A . 1.331(9) ?
C14 F1A . 1.332(10) ?
C14 F2 . 1.335(6) ?
C14 F2A . 1.349(9) ?
C14 F1 . 1.365(6) ?
C15 N16 . 1.328(5) ?
C15 H15 . 0.9500 ?
N16 C18 . 1.457(5) ?
N16 C17 . 1.461(5) ?
C17 H17A . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 0.9800 ?
C18 H18A . 0.9800 ?
C18 H18B . 0.9800 ?
C18 H18C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N7 H7 O6 1_655 0.79(5) 2.14(5) 2.899(5) 162(4) yes
C9 H9 N3 1_555 0.95 2.33 2.905(5) 118 yes
C15 H15 O6 1_655 0.95 2.45 3.317(5) 151 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 S1 C2 O6 . . . . 179.3(3) ?
C5 S1 C2 N3 . . . . 0.2(3) ?
O6 C2 N3 C4 . . . . -178.8(4) ?
S1 C2 N3 C4 . . . . 0.2(4) ?
C2 N3 C4 N7 . . . . 179.2(3) ?
C2 N3 C4 C5 . . . . -0.7(4) ?
N3 C4 C5 C15 . . . . -174.0(3) ?
N7 C4 C5 C15 . . . . 6.2(5) ?
N3 C4 C5 S1 . . . . 0.8(4) ?
N7 C4 C5 S1 . . . . -179.1(3) ?
C2 S1 C5 C15 . . . . 174.1(3) ?
C2 S1 C5 C4 . . . . -0.5(2) ?
N3 C4 N7 C8 . . . . -1.2(5) ?
C5 C4 N7 C8 . . . . 178.6(3) ?
C4 N7 C8 C9 . . . . -20.3(6) ?
C4 N7 C8 C13 . . . . 162.5(4) ?
N7 C8 C9 C10 . . . . -177.6(3) ?
C13 C8 C9 C10 . . . . -0.5(5) ?
C8 C9 C10 C11 . . . . -0.7(6) ?
C8 C9 C10 C14 . . . . 178.4(4) ?
C9 C10 C11 C12 . . . . 1.0(6) ?
C14 C10 C11 C12 . . . . -178.0(4) ?
C10 C11 C12 C13 . . . . -0.2(7) ?
C11 C12 C13 C8 . . . . -1.0(7) ?
C9 C8 C13 C12 . . . . 1.3(6) ?
N7 C8 C13 C12 . . . . 178.7(4) ?
C11 C10 C14 F3 . . . . -0.9(8) ?
C9 C10 C14 F3 . . . . 179.9(7) ?
C11 C10 C14 F3A . . . . 21.9(19) ?
C9 C10 C14 F3A . . . . -157.2(19) ?
C11 C10 C14 F1A . . . . 144(2) ?
C9 C10 C14 F1A . . . . -35(2) ?
C11 C10 C14 F2 . . . . -125.8(8) ?
C9 C10 C14 F2 . . . . 55.1(9) ?
C11 C10 C14 F2A . . . . -97(2) ?
C9 C10 C14 F2A . . . . 84(2) ?
C11 C10 C14 F1 . . . . 118.2(7) ?
C9 C10 C14 F1 . . . . -60.9(7) ?
C4 C5 C15 N16 . . . . -174.8(3) ?
S1 C5 C15 N16 . . . . 11.6(5) ?
C5 C15 N16 C18 . . . . 10.7(6) ?
C5 C15 N16 C17 . . . . -166.4(4) ?

_cod_database_fobs_code 2312321
