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#$Date: 2025-04-05 06:43:16 +0300 (Sat, 05 Apr 2025) $
#$Revision: 299008 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/35/7063533.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_7063533
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_moiety         'C14 H20 N2 O2 S4 Zn'
_chemical_formula_sum            'C14 H20 N2 O2 S4 Zn'
_chemical_formula_weight         441.93
_chemical_name_systematic
Bis[4-(tert-butyl)-3-hydroxythiazole-2(3H)-thionolato]zinc(II)
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc2l01qd
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2024-09-11 deposited with the CCDC.	2024-11-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.2029(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6523(3)
_cell_length_b                   21.5296(8)
_cell_length_c                   10.1015(4)
_cell_measurement_reflns_used    5587
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      2.28
_cell_volume                     1831.97(12)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10590
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         2.596
_exptl_absorpt_coefficient_mu    1.805
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6775
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             912
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane/n-hexane'
_exptl_crystal_size_max          0.354
_exptl_crystal_size_mid          0.241
_exptl_crystal_size_min          0.203
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3608
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0223
_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/[σ²(Fo²)+(0.0285P)²+0.7059P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0553
_refine_ls_wR_factor_ref         0.0570
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3334
_reflns_number_total             3608
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4nj04035j2.cif
_cod_data_source_block           aaa
_cod_depositor_comments
'Adding full bibliography for 7063530--7063535.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7063533
_shelx_shelxl_version_number     2014/7
_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. 
;
_shelx_estimated_absorpt_t_min   0.568
_shelx_estimated_absorpt_t_max   0.711
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.81288(2) 0.42791(2) 0.83237(2) 0.01390(7) Uani 1 1 d . . . . .
S1 S 0.75496(5) 0.53221(2) 0.82042(4) 0.01706(10) Uani 1 1 d . . . . .
S2 S 0.62620(5) 0.58713(2) 1.05049(4) 0.01655(10) Uani 1 1 d . . . . .
S3 S 0.99432(5) 0.37379(2) 0.74092(4) 0.01637(10) Uani 1 1 d . . . . .
S4 S 0.88159(5) 0.25884(2) 0.57023(5) 0.01968(11) Uani 1 1 d . . . . .
O1 O 0.80650(15) 0.42692(5) 1.02678(12) 0.0156(3) Uani 1 1 d . . . . .
O2 O 0.63973(14) 0.37432(5) 0.72608(12) 0.0152(2) Uani 1 1 d . . . . .
N1 N 0.74599(16) 0.48031(6) 1.06317(14) 0.0126(3) Uani 1 1 d . . . . .
N2 N 0.69562(16) 0.32822(6) 0.65934(14) 0.0127(3) Uani 1 1 d . . . . .
C1 C 0.7145(2) 0.52907(7) 0.97808(17) 0.0135(3) Uani 1 1 d . . . . .
C2 C 0.6396(2) 0.54395(8) 1.19604(17) 0.0160(3) Uani 1 1 d . . . . .
H2A H 0.6036 0.5582 1.2728 0.019 Uiso 1 1 calc R U . . .
C3 C 0.70631(19) 0.48788(8) 1.18979(17) 0.0141(3) Uani 1 1 d . . . . .
C4 C 0.7434(2) 0.43920(8) 1.30115(17) 0.0159(4) Uani 1 1 d . . . . .
C5 C 0.6903(2) 0.46436(9) 1.42609(18) 0.0218(4) Uani 1 1 d . . . . .
H5A H 0.7133 0.4335 1.4993 0.033 Uiso 1 1 calc R U . . .
H5B H 0.7477 0.5029 1.4568 0.033 Uiso 1 1 calc R U . . .
H5C H 0.5759 0.4727 1.4018 0.033 Uiso 1 1 calc R U . . .
C6 C 0.6542(2) 0.37821(8) 1.25601(18) 0.0193(4) Uani 1 1 d . . . . .
H6A H 0.6804 0.3477 1.3298 0.029 Uiso 1 1 calc R U . . .
H6B H 0.5396 0.3860 1.2341 0.029 Uiso 1 1 calc R U . . .
H6C H 0.6859 0.3620 1.1754 0.029 Uiso 1 1 calc R U . . .
C7 C 0.9239(2) 0.42749(9) 1.33986(19) 0.0229(4) Uani 1 1 d . . . . .
H7A H 0.9481 0.3961 1.4118 0.034 Uiso 1 1 calc R U . . .
H7B H 0.9593 0.4127 1.2599 0.034 Uiso 1 1 calc R U . . .
H7C H 0.9790 0.4662 1.3725 0.034 Uiso 1 1 calc R U . . .
C8 C 0.8502(2) 0.32345(7) 0.65982(17) 0.0137(3) Uani 1 1 d . . . . .
C9 C 0.6818(2) 0.24097(8) 0.53293(18) 0.0185(4) Uani 1 1 d . . . . .
H9A H 0.6373 0.2061 0.4802 0.022 Uiso 1 1 calc R U . . .
C10 C 0.5960(2) 0.28203(7) 0.58692(17) 0.0140(3) Uani 1 1 d . . . . .
C11 C 0.4187(2) 0.28254(8) 0.57754(17) 0.0161(4) Uani 1 1 d . . . . .
C12 C 0.3431(2) 0.22643(9) 0.4937(2) 0.0234(4) Uani 1 1 d . . . . .
H12A H 0.2284 0.2265 0.4873 0.035 Uiso 1 1 calc R U . . .
H12B H 0.3633 0.2288 0.4023 0.035 Uiso 1 1 calc R U . . .
H12C H 0.3894 0.1881 0.5381 0.035 Uiso 1 1 calc R U . . .
C13 C 0.3876(2) 0.27667(8) 0.72130(18) 0.0204(4) Uani 1 1 d . . . . .
H13A H 0.2730 0.2770 0.7153 0.031 Uiso 1 1 calc R U . . .
H13B H 0.4329 0.2376 0.7627 0.031 Uiso 1 1 calc R U . . .
H13C H 0.4372 0.3117 0.7773 0.031 Uiso 1 1 calc R U . . .
C14 C 0.3443(2) 0.34206(8) 0.50504(19) 0.0212(4) Uani 1 1 d . . . . .
H14A H 0.2297 0.3420 0.4994 0.032 Uiso 1 1 calc R U . . .
H14B H 0.3924 0.3785 0.5564 0.032 Uiso 1 1 calc R U . . .
H14C H 0.3635 0.3435 0.4132 0.032 Uiso 1 1 calc R U . . .
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
O1 Zn1 O2 109.87(5) . . ?
O1 Zn1 S1 90.43(3) . . ?
O2 Zn1 S1 114.09(4) . . ?
O1 Zn1 S3 124.56(4) . . ?
O2 Zn1 S3 89.34(3) . . ?
S1 Zn1 S3 129.181(17) . . ?
C1 S1 Zn1 90.05(6) . . ?
C1 S2 C2 91.21(8) . . ?
C8 S3 Zn1 91.33(6) . . ?
C8 S4 C9 91.39(8) . . ?
N1 O1 Zn1 111.23(9) . . ?
N2 O2 Zn1 112.50(9) . . ?
C1 N1 O1 121.72(14) . . ?
C1 N1 C3 115.76(14) . . ?
O1 N1 C3 122.48(13) . . ?
C8 N2 O2 121.70(14) . . ?
C8 N2 C10 116.12(14) . . ?
O2 N2 C10 122.17(13) . . ?
N1 C1 S1 124.91(13) . . ?
N1 C1 S2 109.97(12) . . ?
S1 C1 S2 125.12(10) . . ?
C3 C2 S2 112.98(13) . . ?
C2 C3 N1 110.05(15) . . ?
C2 C3 C4 127.24(15) . . ?
N1 C3 C4 122.65(14) . . ?
C3 C4 C5 108.24(14) . . ?
C3 C4 C6 111.29(14) . . ?
C5 C4 C6 108.69(14) . . ?
C3 C4 C7 109.36(14) . . ?
C5 C4 C7 108.96(15) . . ?
C6 C4 C7 110.24(15) . . ?
N2 C8 S3 124.77(12) . . ?
N2 C8 S4 109.80(12) . . ?
S3 C8 S4 125.43(10) . . ?
C10 C9 S4 112.49(13) . . ?
C9 C10 N2 110.19(15) . . ?
C9 C10 C11 128.55(15) . . ?
N2 C10 C11 121.26(14) . . ?
C10 C11 C12 109.08(14) . . ?
C10 C11 C13 109.42(14) . . ?
C12 C11 C13 108.14(14) . . ?
C10 C11 C14 110.05(14) . . ?
C12 C11 C14 108.26(15) . . ?
C13 C11 C14 111.83(14) . . ?
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
Zn1 O1 1.9772(12) . ?
Zn1 O2 1.9984(12) . ?
Zn1 S1 2.2979(5) . ?
Zn1 S3 2.3104(5) . ?
S1 C1 1.7082(17) . ?
S2 C1 1.7138(17) . ?
S2 C2 1.7209(17) . ?
S3 C8 1.7132(17) . ?
S4 C8 1.7148(16) . ?
S4 C9 1.7265(18) . ?
O1 N1 1.3485(17) . ?
O2 N2 1.3500(17) . ?
N1 C1 1.345(2) . ?
N1 C3 1.407(2) . ?
N2 C8 1.340(2) . ?
N2 C10 1.407(2) . ?
C2 C3 1.346(2) . ?
C3 C4 1.517(2) . ?
C4 C5 1.537(2) . ?
C4 C6 1.538(2) . ?
C4 C7 1.541(3) . ?
C9 C10 1.347(2) . ?
C10 C11 1.515(2) . ?
C11 C12 1.533(2) . ?
C11 C13 1.541(2) . ?
C11 C14 1.542(2) . ?
