#------------------------------------------------------------------------------
#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/49/7224967.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7224967
loop_
_publ_author_name
'Phukan, Nithi'
'Baruah, Jubaraj B.'
_publ_section_title
;
 Imine-tautomers of aminothiazole derivatives: intriguing aspects of
 chemical reactivities
;
_journal_issue                   21
_journal_name_full               CrystEngComm
_journal_page_first              3877
_journal_paper_doi               10.1039/C6CE00676K
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C11 H10 N4 O2 S2, C4 H9 N O'
_chemical_formula_sum            'C15 H19 N5 O3 S2'
_chemical_formula_weight         381.47
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-01-04 deposited with the CCDC.
2016-04-20 downloaded from the CCDC.
;
_cell_angle_alpha                93.909(4)
_cell_angle_beta                 107.379(4)
_cell_angle_gamma                107.982(4)
_cell_formula_units_Z            2
_cell_length_a                   8.5882(6)
_cell_length_b                   9.0566(7)
_cell_length_c                   13.2569(9)
_cell_measurement_reflns_used    4193
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.59
_cell_measurement_theta_min      2.40
_cell_volume                     921.26(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12000
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.40
_exptl_absorpt_coefficient_mu    0.313
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3152
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0398
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.6000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0739
_refine_ls_wR_factor_ref         0.0802
_reflns_number_gt                2348
_reflns_number_total             3152
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ce00676k2.cif
_cod_data_source_block           4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7224966--7224975.cif.
;
_cod_original_cell_volume        921.26(11)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7224967
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S2 S 0.15430(9) 0.74647(7) 0.02646(5) 0.0542(2) Uani 1 1 d .
S1 S 0.26176(8) 1.09627(7) 0.08753(5) 0.05046(19) Uani 1 1 d .
O1 O -0.3987(3) 0.2900(3) 0.45659(19) 0.1084(9) Uani 1 1 d .
O2 O -0.2711(4) 0.5235(3) 0.55005(19) 0.1088(9) Uani 1 1 d .
N1 N 0.1396(3) 1.1434(2) 0.23286(16) 0.0478(5) Uani 1 1 d .
N2 N 0.0748(2) 0.8762(2) 0.18694(14) 0.0445(5) Uani 1 1 d .
N3 N -0.0046(2) 0.6068(2) 0.15402(15) 0.0494(5) Uani 1 1 d .
H3A H -0.0116 0.5260 0.1125 0.059 Uiso 1 1 calc R
N4 N -0.3029(3) 0.4269(3) 0.4714(2) 0.0730(7) Uani 1 1 d .
C1 C 0.3839(4) 1.4256(3) 0.0938(2) 0.0739(9) Uani 1 1 d .
H1A H 0.3580 1.5171 0.1133 0.111 Uiso 1 1 calc R
H1B H 0.3444 1.3977 0.0170 0.111 Uiso 1 1 calc R
H1C H 0.5072 1.4483 0.1221 0.111 Uiso 1 1 calc R
C2 C 0.2929(3) 1.2902(3) 0.1395(2) 0.0511(6) Uani 1 1 d .
C3 C 0.2195(3) 1.2914(3) 0.21481(19) 0.0517(6) Uani 1 1 d .
H3 H 0.2219 1.3835 0.2518 0.062 Uiso 1 1 calc R
C4 C 0.1483(3) 1.0230(3) 0.17314(17) 0.0421(6) Uani 1 1 d .
C5 C 0.0733(3) 0.7499(3) 0.12848(17) 0.0424(6) Uani 1 1 d .
C6 C -0.0746(3) 0.5703(3) 0.23640(18) 0.0436(6) Uani 1 1 d .
C11 C -0.0438(4) 0.6774(3) 0.32612(19) 0.0594(7) Uani 1 1 d .
H11 H 0.0261 0.7819 0.3341 0.071 Uiso 1 1 calc R
C10 C -0.1162(4) 0.6298(3) 0.4036(2) 0.0625(8) Uani 1 1 d .
H10 H -0.0930 0.7014 0.4645 0.075 Uiso 1 1 calc R
C9 C -0.2224(3) 0.4767(3) 0.39045(19) 0.0513(6) Uani 1 1 d .
C8 C -0.2536(4) 0.3676(3) 0.3032(2) 0.0606(7) Uani 1 1 d .
H8 H -0.3244 0.2635 0.2958 0.073 Uiso 1 1 calc R
C7 C -0.1788(3) 0.4145(3) 0.2269(2) 0.0565(7) Uani 1 1 d .
H7 H -0.1982 0.3408 0.1680 0.068 Uiso 1 1 calc R
O3 O 0.9128(2) 1.0688(2) 0.34718(13) 0.0608(5) Uani 1 1 d .
N5 N 0.6601(3) 0.9178(3) 0.35898(16) 0.0594(6) Uani 1 1 d .
C14 C 0.7603(3) 0.9772(3) 0.3018(2) 0.0536(7) Uani 1 1 d .
C13 C 0.7294(4) 0.9607(4) 0.47639(19) 0.0701(9) Uani 1 1 d .
H13A H 0.8537 0.9902 0.5005 0.105 Uiso 1 1 calc R
H13B H 0.6813 0.8721 0.5072 0.105 Uiso 1 1 calc R
H13C H 0.6986 1.0478 0.4984 0.105 Uiso 1 1 calc R
C12 C 0.4798(4) 0.8107(5) 0.3131(2) 0.1091(14) Uani 1 1 d .
H12A H 0.4474 0.7886 0.2364 0.164 Uiso 1 1 calc R
H12B H 0.4050 0.8590 0.3321 0.164 Uiso 1 1 calc R
H12C H 0.4686 0.7141 0.3408 0.164 Uiso 1 1 calc R
C15 C 0.6871(4) 0.9309(4) 0.1812(2) 0.0713(8) Uani 1 1 d .
H15A H 0.7680 0.9925 0.1505 0.107 Uiso 1 1 calc R
H15B H 0.5791 0.9496 0.1549 0.107 Uiso 1 1 calc R
H15C H 0.6674 0.8210 0.1614 0.107 Uiso 1 1 calc R
H1 H 0.074(3) 1.128(3) 0.276(2) 0.064(8) Uiso 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
C4 S1 C2 91.04(11)
C4 N1 C3 115.6(2)
C4 N1 H1 121.9(16)
C3 N1 H1 122.0(16)
C5 N2 C4 122.57(18)
C5 N3 C6 131.06(19)
C5 N3 H3A 114.5
C6 N3 H3A 114.5
O2 N4 O1 123.2(2)
O2 N4 C9 118.6(2)
O1 N4 C9 118.2(2)
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C3 C2 C1 129.5(2)
C3 C2 S1 110.31(17)
C1 C2 S1 120.08(19)
C2 C3 N1 113.8(2)
C2 C3 H3 123.1
N1 C3 H3 123.1
N2 C4 N1 118.91(19)
N2 C4 S1 131.85(17)
N1 C4 S1 109.24(16)
N2 C5 N3 115.54(19)
N2 C5 S2 127.26(17)
N3 C5 S2 117.20(16)
C11 C6 C7 118.6(2)
C11 C6 N3 124.5(2)
C7 C6 N3 116.86(19)
C10 C11 C6 120.3(2)
C10 C11 H11 119.8
C6 C11 H11 119.8
C9 C10 C11 119.7(2)
C9 C10 H10 120.1
C11 C10 H10 120.1
C10 C9 C8 121.2(2)
C10 C9 N4 119.8(2)
C8 C9 N4 119.0(2)
C9 C8 C7 119.0(2)
C9 C8 H8 120.5
C7 C8 H8 120.5
C8 C7 C6 121.1(2)
C8 C7 H7 119.5
C6 C7 H7 119.5
C14 N5 C12 124.6(2)
C14 N5 C13 119.6(2)
C12 N5 C13 115.8(2)
O3 C14 N5 120.6(2)
O3 C14 C15 120.6(2)
N5 C14 C15 118.8(2)
N5 C13 H13A 109.5
N5 C13 H13B 109.5
H13A C13 H13B 109.5
N5 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
N5 C12 H12A 109.5
N5 C12 H12B 109.5
H12A C12 H12B 109.5
N5 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C14 C15 H15A 109.5
C14 C15 H15B 109.5
H15A C15 H15B 109.5
C14 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S2 C5 1.698(2)
S1 C4 1.744(2)
S1 C2 1.751(2)
O1 N4 1.222(3)
O2 N4 1.218(3)
N1 C4 1.338(3)
N1 C3 1.378(3)
N1 H1 0.90(2)
N2 C5 1.332(3)
N2 C4 1.336(3)
N3 C5 1.379(3)
N3 C6 1.408(3)
N3 H3A 0.8600
N4 C9 1.466(3)
C1 C2 1.508(3)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 C3 1.331(3)
C3 H3 0.9300
C6 C11 1.387(3)
C6 C7 1.391(3)
C11 C10 1.381(3)
C11 H11 0.9300
C10 C9 1.370(3)
C10 H10 0.9300
C9 C8 1.371(3)
C8 C7 1.377(3)
C8 H8 0.9300
C7 H7 0.9300
O3 C14 1.247(3)
N5 C14 1.329(3)
N5 C12 1.462(3)
N5 C13 1.466(3)
C14 C15 1.508(3)
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
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
C4 S1 C2 C3 -0.4(2)
C4 S1 C2 C1 -177.3(2)
C1 C2 C3 N1 176.7(3)
S1 C2 C3 N1 0.2(3)
C4 N1 C3 C2 0.2(3)
C5 N2 C4 N1 177.9(2)
C5 N2 C4 S1 -2.1(4)
C3 N1 C4 N2 179.5(2)
C3 N1 C4 S1 -0.5(3)
C2 S1 C4 N2 -179.5(2)
C2 S1 C4 N1 0.45(19)
C4 N2 C5 N3 178.7(2)
C4 N2 C5 S2 -1.9(4)
C6 N3 C5 N2 -4.5(4)
C6 N3 C5 S2 176.1(2)
C5 N3 C6 C11 -15.4(4)
C5 N3 C6 C7 166.0(2)
C7 C6 C11 C10 -0.4(4)
N3 C6 C11 C10 -179.0(3)
C6 C11 C10 C9 -1.5(4)
C11 C10 C9 C8 2.3(4)
C11 C10 C9 N4 -178.5(3)
O2 N4 C9 C10 -1.1(4)
O1 N4 C9 C10 179.1(3)
O2 N4 C9 C8 178.1(3)
O1 N4 C9 C8 -1.6(4)
C10 C9 C8 C7 -1.1(4)
N4 C9 C8 C7 179.6(3)
C9 C8 C7 C6 -0.9(4)
C11 C6 C7 C8 1.6(4)
N3 C6 C7 C8 -179.7(2)
C12 N5 C14 O3 179.6(3)
C13 N5 C14 O3 0.1(4)
C12 N5 C14 C15 -0.9(4)
C13 N5 C14 C15 179.6(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139201991
