#------------------------------------------------------------------------------
#$Date: 2025-04-05 06:43:16 +0300 (Sat, 05 Apr 2025) $
#$Revision: 299008 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/35/7063534.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_7063534
loop_
_publ_author_name
'Saito, Ryota'
'Naito, Yuki'
'Yoshikawa, Yutaka'
'Yasui, Hiroyuki'
'Kikkawa, Shoko'
'Ju, Huiyeong'
'Ohba, Rintaro'
'Miyamoto, Tae'
'Sano, Shogo'
'Maeda, Kazuya'
'Tamura, Mako'
'Azumaya, Isao'
_publ_section_title
;
 Synthesis, crystal structure, and insulin-mimetic activity of zinc(ii)
 complexes with 4-alkyl- and 4,5-dialkyl-3-hydroxythiazole-2(3H)-thiones
 as a new class of hypoglycemic agent candidates
;
_journal_issue                   4
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1145
_journal_page_last               1158
_journal_paper_doi               10.1039/D4NJ04035J
_journal_volume                  49
_journal_year                    2025
_chemical_formula_sum            'C15 H17 N3 O2 S4 Zn'
_chemical_formula_weight         464.93
_chemical_name_systematic
Bis[3-hydroxy-4,5-dimethyl-2-thioxo-3-thiazololato]zinc(II)
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc2l01nb
_audit_creation_method           SHELXL-97
_audit_update_record
;
2024-09-11 deposited with the CCDC.	2024-11-12 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 103.7934(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.3806(3)
_cell_length_b                   13.3652(4)
_cell_length_c                   9.0229(3)
_cell_measurement_reflns_used    9883
_cell_measurement_temperature    120
_cell_measurement_theta_max      27.90
_cell_measurement_theta_min      2.32
_cell_volume                     981.50(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0103
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            25560
_diffrn_reflns_theta_full        27.90
_diffrn_reflns_theta_max         27.90
_diffrn_reflns_theta_min         2.32
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.690
_exptl_absorpt_correction_T_max  0.7518
_exptl_absorpt_correction_T_min  0.5505
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS; Sheldrick 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane/n-hexane'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.011(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         4202
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0169
_refine_ls_R_factor_gt           0.0168
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0253P)²+0.1520P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0444
_refine_ls_wR_factor_ref         0.0445
_reflns_number_gt                4170
_reflns_number_total             4202
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d4nj04035j2.cif
_cod_data_source_block           mono_p21
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7063530--7063535.cif.
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7063534
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C6 C 0.81904(17) 0.70662(12) 0.40247(15) 0.0181(3) Uani 1 1 d . . .
Zn1 Zn 0.760935(18) 0.692442(12) 0.061854(17) 0.01614(5) Uani 1 1 d . . .
S3 S 0.87657(5) 0.70374(3) 0.59926(4) 0.02474(8) Uani 1 1 d . . .
S4 S 0.70216(5) 0.62061(3) 0.28596(4) 0.02169(8) Uani 1 1 d . . .
S2 S 0.60555(5) 0.79759(3) -0.13181(5) 0.02298(9) Uani 1 1 d . . .
S1 S 0.39810(6) 0.70652(4) -0.42653(5) 0.03293(11) Uani 1 1 d . . .
C1 C 0.52662(17) 0.69937(15) -0.24631(15) 0.0210(3) Uani 1 1 d . . .
O1 O 0.65152(14) 0.57375(9) -0.07543(13) 0.0203(2) Uani 1 1 d . . .
N2 N 0.88125(16) 0.78880(10) 0.35324(14) 0.0168(2) Uani 1 1 d . . .
N1 N 0.55632(16) 0.60322(10) -0.20954(16) 0.0189(2) Uani 1 1 d . . .
N3 N 0.99635(15) 0.65128(10) 0.04140(15) 0.0173(2) Uani 1 1 d . . .
C8 C 0.9868(2) 0.81456(12) 0.60730(18) 0.0230(3) Uani 1 1 d . . .
C3 C 0.3882(2) 0.57629(16) -0.44484(19) 0.0326(4) Uani 1 1 d . . .
C12 C 1.1736(2) 0.52944(13) -0.03090(18) 0.0226(3) Uani 1 1 d . . .
H12 H 1.1859 0.4671 -0.0727 0.027 Uiso 1 1 calc R . .
C13 C 1.30830(19) 0.59075(14) 0.02065(18) 0.0228(3) Uani 1 1 d . . .
H13 H 1.4127 0.5704 0.0147 0.027 Uiso 1 1 calc R . .
C2 C 0.4790(2) 0.53262(14) -0.31810(19) 0.0247(3) Uani 1 1 d . . .
C15 C 1.12732(18) 0.71061(12) 0.09026(18) 0.0218(3) Uani 1 1 d . . .
H15 H 1.1123 0.7726 0.1317 0.026 Uiso 1 1 calc R . .
C7 C 0.9772(2) 0.85022(12) 0.46506(17) 0.0215(3) Uani 1 1 d . . .
C10 C 1.0749(3) 0.85767(15) 0.7575(2) 0.0339(4) Uani 1 1 d . . .
H10A H 1.1107 0.9243 0.7425 0.051 Uiso 1 1 calc R . .
H10B H 1.1685 0.8169 0.8014 0.051 Uiso 1 1 calc R . .
H10C H 1.0021 0.8595 0.8250 0.051 Uiso 1 1 calc R . .
C11 C 1.01988(19) 0.56215(12) -0.01939(18) 0.0206(3) Uani 1 1 d . . .
H11 H 0.9296 0.5208 -0.0551 0.025 Uiso 1 1 calc R . .
C9 C 1.0487(3) 0.94244(15) 0.4160(2) 0.0336(4) Uani 1 1 d . . .
H9A H 1.1222 0.9726 0.5025 0.050 Uiso 1 1 calc R . .
H9B H 0.9621 0.9886 0.3733 0.050 Uiso 1 1 calc R . .
H9C H 1.1080 0.9258 0.3405 0.050 Uiso 1 1 calc R . .
C14 C 1.28421(18) 0.68315(16) 0.08134(19) 0.0255(3) Uani 1 1 d . . .
H14 H 1.3724 0.7263 0.1157 0.031 Uiso 1 1 calc R . .
C4 C 0.5054(2) 0.42430(14) -0.2804(2) 0.0310(4) Uani 1 1 d . . .
H4A H 0.4623 0.3850 -0.3701 0.047 Uiso 1 1 calc R . .
H4B H 0.4501 0.4067 -0.2024 0.047 Uiso 1 1 calc R . .
H4C H 0.6209 0.4114 -0.2445 0.047 Uiso 1 1 calc R . .
O2 O 0.85311(14) 0.81279(8) 0.20442(12) 0.0200(2) Uani 1 1 d . . .
C5 C 0.2922(3) 0.5284(2) -0.5883(2) 0.0517(7) Uani 1 1 d . . .
H5A H 0.2782 0.4585 -0.5704 0.078 Uiso 1 1 calc R . .
H5B H 0.3503 0.5362 -0.6673 0.078 Uiso 1 1 calc R . .
H5C H 0.1865 0.5599 -0.6192 0.078 Uiso 1 1 calc R . .
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'
Zn Zn 0.2839 1.4301 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C6 S4 124.24(11) . . ?
N2 C6 S3 108.96(11) . . ?
S4 C6 S3 126.80(9) . . ?
O1 Zn1 O2 175.50(5) . . ?
O1 Zn1 N3 92.17(5) . . ?
O2 Zn1 N3 92.21(5) . . ?
O1 Zn1 S2 85.80(4) . . ?
O2 Zn1 S2 93.14(3) . . ?
N3 Zn1 S2 116.91(4) . . ?
O1 Zn1 S4 92.68(3) . . ?
O2 Zn1 S4 84.78(3) . . ?
N3 Zn1 S4 110.88(4) . . ?
S2 Zn1 S4 132.211(15) . . ?
C6 S3 C8 92.24(8) . . ?
C6 S4 Zn1 92.69(5) . . ?
C1 S2 Zn1 93.19(6) . . ?
C1 S1 C3 92.23(9) . . ?
N1 C1 S2 124.63(11) . . ?
N1 C1 S1 108.95(13) . . ?
S2 C1 S1 126.41(12) . . ?
N1 O1 Zn1 113.30(9) . . ?
C6 N2 O2 122.55(12) . . ?
C6 N2 C7 116.48(12) . . ?
O2 N2 C7 120.96(12) . . ?
C1 N1 O1 122.87(13) . . ?
C1 N1 C2 116.50(14) . . ?
O1 N1 C2 120.62(14) . . ?
C15 N3 C11 118.01(13) . . ?
C15 N3 Zn1 121.96(11) . . ?
C11 N3 Zn1 120.01(10) . . ?
C7 C8 C10 128.92(16) . . ?
C7 C8 S3 110.49(12) . . ?
C10 C8 S3 120.59(13) . . ?
C2 C3 C5 128.9(2) . . ?
C2 C3 S1 110.29(14) . . ?
C5 C3 S1 120.76(17) . . ?
C13 C12 C11 119.09(15) . . ?
C12 C13 C14 118.51(14) . . ?
C3 C2 N1 112.03(16) . . ?
C3 C2 C4 129.59(17) . . ?
N1 C2 C4 118.38(15) . . ?
N3 C15 C14 122.55(16) . . ?
C8 C7 N2 111.81(14) . . ?
C8 C7 C9 129.70(15) . . ?
N2 C7 C9 118.47(14) . . ?
N3 C11 C12 122.56(15) . . ?
C13 C14 C15 119.26(16) . . ?
N2 O2 Zn1 112.47(9) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C6 N2 1.336(2) . ?
C6 S4 1.7015(15) . ?
C6 S3 1.7259(14) . ?
Zn1 O1 2.0857(11) . ?
Zn1 O2 2.0892(11) . ?
Zn1 N3 2.0983(13) . ?
Zn1 S2 2.3747(4) . ?
Zn1 S4 2.3933(4) . ?
S3 C8 1.7378(18) . ?
S2 C1 1.7037(19) . ?
S1 C1 1.7257(14) . ?
S1 C3 1.748(2) . ?
C1 N1 1.336(2) . ?
O1 N1 1.3400(18) . ?
N2 O2 1.3455(15) . ?
N2 C7 1.397(2) . ?
N1 C2 1.402(2) . ?
N3 C15 1.341(2) . ?
N3 C11 1.346(2) . ?
C8 C7 1.353(2) . ?
C8 C10 1.496(2) . ?
C3 C2 1.346(3) . ?
C3 C5 1.495(3) . ?
C12 C13 1.382(2) . ?
C12 C11 1.388(2) . ?
C13 C14 1.385(3) . ?
C2 C4 1.491(3) . ?
C15 C14 1.386(2) . ?
C7 C9 1.483(2) . ?
