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#$Date: 2025-03-04 22:25:09 +0200 (Tue, 04 Mar 2025) $
#$Revision: 298288 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/75/7717518.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_7717518
loop_
_publ_author_name
'Avcu Altiparmak, Elif'
'Özen Eroğlu, Güneş'
'Özdemir, Namık'
'Erdem Kuruca, Serap'
'Bal Demirci, Tülay'
_publ_section_title
;
 Synthesis, cytotoxicities, structural properties and comparison of
 dihalogeno-substituted-thiosemicarbazone ligands and mixed-ligand Ni(II)
 complexes.
;
_journal_issue                   4
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1454
_journal_page_last               1467
_journal_paper_doi               10.1039/d4dt02774d
_journal_volume                  54
_journal_year                    2025
_chemical_formula_moiety         'C13 H18 Br2 N4 Ni O3 S'
_chemical_formula_sum            'C13 H18 Br2 N4 Ni O3 S'
_chemical_formula_weight         528.90
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2023-08-10 deposited with the CCDC.	2024-11-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.571(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6900(8)
_cell_length_b                   10.2688(5)
_cell_length_c                   15.4499(12)
_cell_measurement_reflns_used    17350
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.11
_cell_measurement_theta_min      1.98
_cell_volume                     1872.3(2)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material
'OLEX2 (Dolomanov et al., 2009) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    '0.8 mm diameter, multiple pinhole'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0812
_diffrn_reflns_av_unetI/netI     0.0634
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15384
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.760
_diffrn_reflns_theta_min         2.438
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_exptl_absorpt_coefficient_mu    5.435
_exptl_absorpt_correction_T_max  0.3556
_exptl_absorpt_correction_T_min  0.0300
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'X-RED32 (Stoe & Cie, 2002)'
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.876
_exptl_crystal_description       prism
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.740
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.833
_refine_diff_density_min         -0.551
_refine_diff_density_rms         0.128
_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     220
_refine_ls_number_reflns         4379
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0506
_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)+(0.0551P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1171
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3039
_reflns_number_total             4379
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt02774d2.cif
_cod_data_source_block           namiko281
_cod_depositor_comments
'Adding full bibliography for 7717516--7717518.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7717518
_shelx_shelxl_version_number     2019/3
_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   0.108
_shelx_estimated_absorpt_t_max   0.395
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_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
Ni1 Ni 0.62669(5) 0.30247(5) 0.52219(4) 0.03437(15) Uani 1 1 d . . . . .
Br1 Br 1.00907(5) 0.36580(6) 0.72432(5) 0.0664(2) Uani 1 1 d . . . . .
Br2 Br 1.02504(6) 0.82002(6) 0.52046(5) 0.0724(2) Uani 1 1 d . . . . .
S1 S 0.28941(11) 0.28946(13) 0.31015(10) 0.0575(4) Uani 1 1 d . . . . .
O1 O 0.7720(3) 0.3568(3) 0.5860(2) 0.0424(7) Uani 1 1 d . . . . .
O2 O 0.5000(5) 0.1301(7) 0.6989(3) 0.108(2) Uani 1 1 d . . . . .
H2 H 0.524171 0.067200 0.733233 0.162 Uiso 1 1 calc R U . . .
O3 O 0.6243(4) -0.0504(4) 0.4722(3) 0.0669(11) Uani 1 1 d . . . . .
H3 H 0.602619 -0.071983 0.417323 0.100 Uiso 1 1 calc R U . . .
N1 N 0.5908(3) 0.4356(3) 0.4350(3) 0.0366(8) Uani 1 1 d . . . . .
N2 N 0.4812(3) 0.4323(3) 0.3656(3) 0.0396(8) Uani 1 1 d . . . . .
N3 N 0.4788(3) 0.2543(4) 0.4561(3) 0.0462(9) Uani 1 1 d . . . . .
H3N H 0.446229 0.189144 0.470775 0.055 Uiso 1 1 calc R U . . .
N4 N 0.6610(3) 0.1490(3) 0.6042(3) 0.0401(8) Uani 1 1 d . . . . .
H4 H 0.593254 0.093822 0.583334 0.048 Uiso 1 1 calc R U . . .
C1 C 0.8230(4) 0.4571(4) 0.5677(3) 0.0366(9) Uani 1 1 d . . . . .
C2 C 0.9375(4) 0.4833(4) 0.6248(4) 0.0444(11) Uani 1 1 d . . . . .
C3 C 0.9965(4) 0.5890(4) 0.6108(4) 0.0489(12) Uani 1 1 d . . . . .
H3A H 1.071026 0.603968 0.650206 0.059 Uiso 1 1 calc R U . . .
C4 C 0.9435(4) 0.6723(4) 0.5376(4) 0.0497(12) Uani 1 1 d . . . . .
C5 C 0.8340(4) 0.6520(4) 0.4789(4) 0.0472(11) Uani 1 1 d . . . . .
H5 H 0.800169 0.709253 0.429877 0.057 Uiso 1 1 calc R U . . .
C6 C 0.7720(4) 0.5448(4) 0.4920(3) 0.0389(10) Uani 1 1 d . . . . .
C7 C 0.6571(4) 0.5282(4) 0.4290(4) 0.0447(11) Uani 1 1 d . . . . .
H7 H 0.628428 0.587769 0.380699 0.054 Uiso 1 1 calc R U . . .
C8 C 0.4285(4) 0.3299(4) 0.3842(3) 0.0403(10) Uani 1 1 d . . . . .
C9 C 0.2422(5) 0.4295(6) 0.2365(4) 0.0589(14) Uani 1 1 d . . . . .
H9A H 0.248129 0.505494 0.274210 0.088 Uiso 1 1 calc R U . . .
H9B H 0.164757 0.417462 0.195959 0.088 Uiso 1 1 calc R U . . .
H9C H 0.288590 0.440504 0.199971 0.088 Uiso 1 1 calc R U . . .
C10 C 0.6869(5) 0.1789(5) 0.7045(4) 0.0524(12) Uani 1 1 d . . . . .
H10A H 0.714064 0.100690 0.741196 0.063 Uiso 1 1 calc R U . . .
H10B H 0.746516 0.243757 0.725272 0.063 Uiso 1 1 calc R U . . .
C11 C 0.5861(6) 0.2277(7) 0.7198(4) 0.0696(16) Uani 1 1 d . . . . .
H11A H 0.607238 0.254628 0.784139 0.083 Uiso 1 1 calc R U . . .
H11B H 0.556508 0.303195 0.680635 0.083 Uiso 1 1 calc R U . . .
C12 C 0.7542(4) 0.0711(4) 0.5938(4) 0.0488(12) Uani 1 1 d . . . . .
H12A H 0.769819 -0.003577 0.635033 0.059 Uiso 1 1 calc R U . . .
H12B H 0.822405 0.123726 0.611531 0.059 Uiso 1 1 calc R U . . .
C13 C 0.7234(5) 0.0250(5) 0.4946(4) 0.0552(13) Uani 1 1 d . . . . .
H13A H 0.710245 0.098877 0.452845 0.066 Uiso 1 1 calc R U . . .
H13B H 0.784454 -0.026902 0.488939 0.066 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'
Br Br -0.2901 2.4595 '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'
Ni Ni 0.3393 1.1124 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Ni1 N3 177.72(15) . . ?
O1 Ni1 N1 95.54(14) . . ?
N3 Ni1 N1 82.35(16) . . ?
O1 Ni1 N4 87.51(14) . . ?
N3 Ni1 N4 94.66(16) . . ?
N1 Ni1 N4 174.25(16) . . ?
C8 S1 C9 104.1(2) . . ?
C1 O1 Ni1 127.4(3) . . ?
C11 O2 H2 109.5 . . ?
C13 O3 H3 109.5 . . ?
C7 N1 N2 116.7(4) . . ?
C7 N1 Ni1 126.9(3) . . ?
N2 N1 Ni1 116.4(3) . . ?
C8 N2 N1 106.8(3) . . ?
C8 N3 Ni1 112.9(3) . . ?
C8 N3 H3N 123.5 . . ?
Ni1 N3 H3N 123.5 . . ?
C12 N4 C10 110.1(4) . . ?
C12 N4 Ni1 111.0(3) . . ?
C10 N4 Ni1 114.5(3) . . ?
C12 N4 H4 106.9 . . ?
C10 N4 H4 106.9 . . ?
Ni1 N4 H4 106.9 . . ?
O1 C1 C2 119.4(4) . . ?
O1 C1 C6 124.4(4) . . ?
C2 C1 C6 116.2(4) . . ?
C3 C2 C1 122.7(4) . . ?
C3 C2 Br1 120.1(4) . . ?
C1 C2 Br1 117.2(3) . . ?
C4 C3 C2 119.2(5) . . ?
C4 C3 H3A 120.4 . . ?
C2 C3 H3A 120.4 . . ?
C5 C4 C3 121.3(4) . . ?
C5 C4 Br2 120.0(4) . . ?
C3 C4 Br2 118.7(4) . . ?
C4 C5 C6 120.6(4) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 120.0(4) . . ?
C5 C6 C7 118.5(4) . . ?
C1 C6 C7 121.5(4) . . ?
N1 C7 C6 124.3(4) . . ?
N1 C7 H7 117.8 . . ?
C6 C7 H7 117.8 . . ?
N3 C8 N2 121.5(4) . . ?
N3 C8 S1 118.0(3) . . ?
N2 C8 S1 120.5(3) . . ?
S1 C9 H9A 109.5 . . ?
S1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
S1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 N4 111.4(4) . . ?
C11 C10 H10A 109.4 . . ?
N4 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
N4 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
O2 C11 C10 111.2(6) . . ?
O2 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 . . ?
O2 C11 H11B 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
N4 C12 C13 111.0(4) . . ?
N4 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
N4 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
O3 C13 C12 107.2(5) . . ?
O3 C13 H13A 110.3 . . ?
C12 C13 H13A 110.3 . . ?
O3 C13 H13B 110.3 . . ?
C12 C13 H13B 110.3 . . ?
H13A C13 H13B 108.5 . . ?
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
Ni1 O1 1.830(3) . ?
Ni1 N3 1.844(4) . ?
Ni1 N1 1.855(3) . ?
Ni1 N4 1.968(3) . ?
Br1 C2 1.901(5) . ?
Br2 C4 1.908(4) . ?
S1 C8 1.764(5) . ?
S1 C9 1.795(6) . ?
O1 C1 1.302(5) . ?
O2 C11 1.429(8) . ?
O2 H2 0.8200 . ?
O3 C13 1.407(6) . ?
O3 H3 0.8200 . ?
N1 C7 1.296(6) . ?
N1 N2 1.410(5) . ?
N2 C8 1.333(6) . ?
N3 C8 1.312(6) . ?
N3 H3N 0.8600 . ?
N4 C12 1.484(6) . ?
N4 C10 1.494(6) . ?
N4 H4 0.9800 . ?
C1 C2 1.421(6) . ?
C1 C6 1.428(6) . ?
C2 C3 1.380(7) . ?
C3 C4 1.380(8) . ?
C3 H3A 0.9300 . ?
C4 C5 1.367(7) . ?
C5 C6 1.410(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.434(6) . ?
C7 H7 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.472(9) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.511(8) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Ni1 O1 C1 -0.8(4) . . . . ?
N4 Ni1 O1 C1 174.3(4) . . . . ?
O1 Ni1 N1 C7 1.3(5) . . . . ?
N3 Ni1 N1 C7 -179.5(5) . . . . ?
O1 Ni1 N1 N2 178.5(3) . . . . ?
N3 Ni1 N1 N2 -2.4(3) . . . . ?
C7 N1 N2 C8 179.3(4) . . . . ?
Ni1 N1 N2 C8 1.9(5) . . . . ?
N1 Ni1 N3 C8 2.3(4) . . . . ?
N4 Ni1 N3 C8 -172.7(4) . . . . ?
Ni1 O1 C1 C2 -179.2(3) . . . . ?
Ni1 O1 C1 C6 0.3(7) . . . . ?
O1 C1 C2 C3 -178.7(5) . . . . ?
C6 C1 C2 C3 1.7(7) . . . . ?
O1 C1 C2 Br1 1.0(6) . . . . ?
C6 C1 C2 Br1 -178.5(3) . . . . ?
C1 C2 C3 C4 -1.0(8) . . . . ?
Br1 C2 C3 C4 179.3(4) . . . . ?
C2 C3 C4 C5 0.0(8) . . . . ?
C2 C3 C4 Br2 178.8(4) . . . . ?
C3 C4 C5 C6 0.2(8) . . . . ?
Br2 C4 C5 C6 -178.6(4) . . . . ?
C4 C5 C6 C1 0.6(8) . . . . ?
C4 C5 C6 C7 179.6(5) . . . . ?
O1 C1 C6 C5 179.0(5) . . . . ?
C2 C1 C6 C5 -1.5(7) . . . . ?
O1 C1 C6 C7 0.0(7) . . . . ?
C2 C1 C6 C7 179.5(5) . . . . ?
N2 N1 C7 C6 -178.5(4) . . . . ?
Ni1 N1 C7 C6 -1.4(8) . . . . ?
C5 C6 C7 N1 -178.4(5) . . . . ?
C1 C6 C7 N1 0.6(8) . . . . ?
Ni1 N3 C8 N2 -2.1(6) . . . . ?
Ni1 N3 C8 S1 176.1(2) . . . . ?
N1 N2 C8 N3 0.2(6) . . . . ?
N1 N2 C8 S1 -178.0(3) . . . . ?
C9 S1 C8 N3 169.2(4) . . . . ?
C9 S1 C8 N2 -12.6(5) . . . . ?
C12 N4 C10 C11 -166.3(4) . . . . ?
Ni1 N4 C10 C11 67.7(5) . . . . ?
N4 C10 C11 O2 64.9(6) . . . . ?
C10 N4 C12 C13 172.7(4) . . . . ?
Ni1 N4 C12 C13 -59.4(4) . . . . ?
N4 C12 C13 O3 -59.0(5) . . . . ?
