#------------------------------------------------------------------------------
#$Date: 2024-10-06 11:10:39 +0300 (Sun, 06 Oct 2024) $
#$Revision: 295275 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/69/7716920.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_7716920
loop_
_publ_author_name
'Besleaga, Iuliana'
'Fesenko, Anastasia A.'
'Paul, Anup'
'Šljukić, Biljana'
'Rapta, Peter'
'Pombeiro, Armando J. L.'
'Shutalev, Anatoly D.'
'Arion, Vladimir B.'
_publ_section_title
;
 Nickel(ii) complexes with 14-membered bis-thiosemicarbazide and
 bis-isothiosemicarbazide ligands: synthesis, characterization and
 catalysis of oxygen evolution reaction
;
_journal_issue                   38
_journal_name_full               'Dalton Transactions'
_journal_page_first              15826
_journal_page_last               15841
_journal_paper_doi               10.1039/D4DT02182G
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C20 H34 N6 S2'
_chemical_formula_sum            'C20 H34 N6 S2'
_chemical_formula_weight         422.65
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2024-01-09 deposited with the CCDC.	2024-08-21 downloaded from the CCDC.
;
_cell_angle_alpha                101.269(5)
_cell_angle_beta                 103.562(6)
_cell_angle_gamma                93.900(6)
_cell_formula_units_Z            2
_cell_length_a                   9.2324(7)
_cell_length_b                   10.4294(7)
_cell_length_c                   12.5483(8)
_cell_measurement_reflns_used    11890
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      71.78
_cell_measurement_theta_min      3.63
_cell_volume                     1143.68(14)
_computing_cell_refinement
;
X-Area Recipe 1.36.0.0 (STOE, 2020)
;
_computing_data_collection
;
X-Area Pilatus3_SV 1.31.170.0 (STOE, 2020)
;
_computing_data_reduction
;
X-Area Integrate 1.78.3.0 (STOE, 2020)
X-Area LANA 1.83.8.0 (STOE, 2020)
;
_computing_publication_material
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.90, Darmstadt 2020
;
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.944
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_av_unetI/netI     0.0111
_diffrn_reflns_Laue_measured_fraction_full 0.944
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23743
_diffrn_reflns_point_group_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.455
_diffrn_reflns_theta_min         3.713
_exptl_absorpt_coefficient_mu    2.238
_exptl_absorpt_correction_T_max  0.7870
_exptl_absorpt_correction_T_min  0.7266
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4154
_refine_ls_number_restraints     468
_refine_ls_restrained_S_all      1.162
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0488
_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)+(0.0766P)²+0.4731P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1389
_refine_ls_wR_factor_ref         0.1456
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3510
_reflns_number_total             4154
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt02182g2.cif
_cod_data_source_block           iubem3
_cod_depositor_comments
'Adding full bibliography for 7716919--7716923.cif.'
_cod_database_code               7716920
_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   0.760
_shelx_estimated_absorpt_t_max   0.791
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_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_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
S1 S 0.71173(11) 0.28336(7) 0.10320(6) 0.0856(3) Uani 1 1 d . U . . .
S2 S 0.91834(7) 0.26170(6) 0.75546(5) 0.0600(2) Uani 1 1 d . U . . .
N1 N 0.6825(2) 0.46079(17) 0.40071(14) 0.0469(4) Uani 1 1 d . U . . .
N2 N 0.7263(2) 0.44167(18) 0.29865(14) 0.0537(4) Uani 1 1 d . U . . .
C3 C 0.6675(3) 0.3282(2) 0.23497(17) 0.0533(5) Uani 1 1 d . U . . .
N4 N 0.5787(2) 0.23737(18) 0.26019(15) 0.0537(5) Uani 1 1 d . U . . .
H4 H 0.5467 0.2616 0.3192 0.064 Uiso 1 1 calc R U . . .
C5 C 0.5308(3) 0.1015(2) 0.19741(17) 0.0512(5) Uani 1 1 d . U . . .
H5 H 0.6127 0.0682 0.1667 0.061 Uiso 1 1 calc R U . . .
C6 C 0.4955(3) 0.0155(2) 0.27698(19) 0.0530(5) Uani 1 1 d . U . . .
H6 H 0.3998 0.0351 0.2937 0.064 Uiso 1 1 calc R U . . .
C7 C 0.6138(3) 0.0310(2) 0.38662(18) 0.0501(5) Uani 1 1 d . U . . .
N8 N 0.6375(2) 0.13684(18) 0.46224(15) 0.0517(4) Uani 1 1 d . U . . .
N9 N 0.7470(2) 0.13178(18) 0.56034(15) 0.0530(4) Uani 1 1 d . U . . .
C10 C 0.7847(2) 0.2475(2) 0.62644(17) 0.0462(5) Uani 1 1 d . U . . .
N11 N 0.7301(2) 0.35942(17) 0.60586(14) 0.0497(4) Uani 1 1 d . U . . .
H11 H 0.6547 0.3502 0.5486 0.060 Uiso 1 1 calc R U . . .
C12 C 0.7829(3) 0.4938(2) 0.66859(16) 0.0472(5) Uani 1 1 d . U . . .
H12 H 0.8928 0.5050 0.6915 0.057 Uiso 1 1 calc R U . . .
C13 C 0.7297(2) 0.5892(2) 0.59156(16) 0.0459(5) Uani 1 1 d . U . . .
H13 H 0.6217 0.5930 0.5816 0.055 Uiso 1 1 calc R U . . .
C14 C 0.7639(2) 0.55337(19) 0.47744(16) 0.0420(4) Uani 1 1 d . U . . .
C15 C 0.3931(3) 0.0949(3) 0.1005(2) 0.0721(7) Uani 1 1 d . U . . .
H15A H 0.4161 0.1494 0.0519 0.108 Uiso 1 1 calc R U . . .
H15B H 0.3115 0.1256 0.1299 0.108 Uiso 1 1 calc R U . . .
H15C H 0.3650 0.0056 0.0589 0.108 Uiso 1 1 calc R U . . .
C16 C 0.7225(4) 0.5240(3) 0.7733(2) 0.0715(7) Uani 1 1 d . U . . .
H16A H 0.6150 0.5179 0.7512 0.107 Uiso 1 1 calc R U . . .
H16B H 0.7628 0.6113 0.8155 0.107 Uiso 1 1 calc R U . . .
H16C H 0.7519 0.4616 0.8190 0.107 Uiso 1 1 calc R U . . .
C17 C 0.8146(3) 0.7288(2) 0.6388(2) 0.0585(6) Uani 1 1 d . U . . .
H17A H 0.7517 0.7945 0.6160 0.070 Uiso 1 1 calc R U . . .
H17B H 0.8460 0.7470 0.7201 0.070 Uiso 1 1 calc R U . . .
C18 C 0.9508(3) 0.7293(2) 0.5891(2) 0.0634(6) Uani 1 1 d . U . . .
H18A H 0.9853 0.8179 0.5857 0.076 Uiso 1 1 calc R U . . .
H18B H 1.0324 0.6939 0.6340 0.076 Uiso 1 1 calc R U . . .
C19 C 0.8957(3) 0.6422(2) 0.47170(19) 0.0514(5) Uani 1 1 d . U . . .
H19A H 0.8654 0.6949 0.4163 0.062 Uiso 1 1 calc R U . . .
H19B H 0.9736 0.5914 0.4523 0.062 Uiso 1 1 calc R U . . .
C20 C 0.4834(3) -0.1330(2) 0.2246(2) 0.0680(7) Uani 1 1 d . U . . .
H20A H 0.3922 -0.1787 0.2317 0.082 Uiso 1 1 calc R U . . .
H20B H 0.4812 -0.1463 0.1455 0.082 Uiso 1 1 calc R U . . .
C21 C 0.6120(5) -0.1822(4) 0.2839(4) 0.1224(15) Uani 1 1 d . U . . .
H21A H 0.6837 -0.1934 0.2384 0.147 Uiso 1 1 calc R U . . .
H21B H 0.5819 -0.2678 0.2965 0.147 Uiso 1 1 calc R U . . .
C22 C 0.6839(4) -0.0931(3) 0.3922(2) 0.0722(7) Uani 1 1 d . U . . .
H22A H 0.7915 -0.0775 0.4020 0.087 Uiso 1 1 calc R U . . .
H22B H 0.6647 -0.1293 0.4538 0.087 Uiso 1 1 calc R U . . .
C23 C 0.8070(4) 0.4324(3) 0.0906(2) 0.0831(8) Uani 1 1 d . U . . .
H23A H 0.8789 0.4707 0.1615 0.100 Uiso 1 1 calc R U . . .
H23B H 0.8629 0.4111 0.0342 0.100 Uiso 1 1 calc R U . . .
C24 C 0.7085(6) 0.5318(4) 0.0599(3) 0.1200(13) Uani 1 1 d . U . . .
H24A H 0.7672 0.6058 0.0496 0.180 Uiso 1 1 calc R U . . .
H24B H 0.6600 0.5603 0.1187 0.180 Uiso 1 1 calc R U . . .
H24C H 0.6340 0.4940 -0.0087 0.180 Uiso 1 1 calc R U . . .
C25 C 0.9518(3) 0.0933(3) 0.7530(2) 0.0709(7) Uani 1 1 d . U . . .
H25A H 0.8567 0.0372 0.7300 0.085 Uiso 1 1 calc R U . . .
H25B H 1.0092 0.0653 0.6989 0.085 Uiso 1 1 calc R U . . .
C26 C 1.0358(5) 0.0797(4) 0.8666(3) 0.1139(13) Uani 1 1 d . U . . .
H26A H 1.0660 -0.0070 0.8618 0.171 Uiso 1 1 calc R U . . .
H26B H 0.9723 0.0936 0.9174 0.171 Uiso 1 1 calc R U . . .
H26C H 1.1230 0.1439 0.8936 0.171 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 0.0181 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'
N N 0.0311 0.0180 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 S1 C23 103.15(13) . . ?
C10 S2 C25 102.08(12) . . ?
C14 N1 N2 113.72(18) . . ?
C3 N2 N1 110.84(18) . . ?
N2 C3 N4 126.1(2) . . ?
N2 C3 S1 118.01(18) . . ?
N4 C3 S1 115.82(16) . . ?
C3 N4 C5 126.61(19) . . ?
N4 C5 C15 110.54(19) . . ?
N4 C5 C6 109.49(17) . . ?
C15 C5 C6 110.2(2) . . ?
C7 C6 C5 115.43(18) . . ?
C7 C6 C20 102.76(19) . . ?
C5 C6 C20 111.99(19) . . ?
N8 C7 C22 128.0(2) . . ?
N8 C7 C6 121.0(2) . . ?
C22 C7 C6 110.80(19) . . ?
C7 N8 N9 113.29(18) . . ?
C10 N9 N8 110.74(17) . . ?
N9 C10 N11 125.83(19) . . ?
N9 C10 S2 117.80(16) . . ?
N11 C10 S2 116.36(16) . . ?
C10 N11 C12 128.05(18) . . ?
N11 C12 C16 110.8(2) . . ?
N11 C12 C13 108.69(16) . . ?
C16 C12 C13 109.96(18) . . ?
C14 C13 C17 101.95(17) . . ?
C14 C13 C12 113.58(16) . . ?
C17 C13 C12 112.01(18) . . ?
N1 C14 C19 128.44(19) . . ?
N1 C14 C13 120.47(19) . . ?
C19 C14 C13 111.06(17) . . ?
C18 C17 C13 105.14(18) . . ?
C19 C18 C17 105.0(2) . . ?
C14 C19 C18 104.71(18) . . ?
C21 C20 C6 107.3(2) . . ?
C20 C21 C22 111.8(3) . . ?
C21 C22 C7 104.5(2) . . ?
C24 C23 S1 114.7(3) . . ?
C26 C25 S2 110.3(2) . . ?
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
S1 C3 1.777(2) . ?
S1 C23 1.786(3) . ?
S2 C10 1.764(2) . ?
S2 C25 1.799(3) . ?
N1 C14 1.274(3) . ?
N1 N2 1.413(2) . ?
N2 C3 1.293(3) . ?
C3 N4 1.343(3) . ?
N4 C5 1.463(3) . ?
C5 C15 1.526(3) . ?
C5 C6 1.539(3) . ?
C6 C7 1.516(3) . ?
C6 C20 1.545(3) . ?
C7 N8 1.276(3) . ?
C7 C22 1.492(3) . ?
N8 N9 1.411(2) . ?
N9 C10 1.297(3) . ?
C10 N11 1.349(3) . ?
N11 C12 1.455(3) . ?
C12 C16 1.530(3) . ?
C12 C13 1.544(3) . ?
C13 C14 1.520(3) . ?
C13 C17 1.542(3) . ?
C14 C19 1.502(3) . ?
C17 C18 1.528(4) . ?
C18 C19 1.522(3) . ?
C20 C21 1.429(5) . ?
C21 C22 1.466(4) . ?
C23 C24 1.472(6) . ?
C25 C26 1.493(4) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4 H4 N8 0.86 2.44 2.880(3) 112.1 .
N11 H11 N1 0.86 2.42 2.921(2) 117.7 .
C15 H15A S1 0.96 2.85 3.415(3) 118.6 .
C16 H16C S2 0.96 2.78 3.380(3) 121.7 .
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
C14 N1 N2 C3 163.40(19) . . . . ?
N1 N2 C3 N4 -1.1(3) . . . . ?
N1 N2 C3 S1 -178.80(15) . . . . ?
C23 S1 C3 N2 -9.7(2) . . . . ?
C23 S1 C3 N4 172.4(2) . . . . ?
N2 C3 N4 C5 -169.6(2) . . . . ?
S1 C3 N4 C5 8.1(3) . . . . ?
C3 N4 C5 C15 -84.3(3) . . . . ?
C3 N4 C5 C6 154.1(2) . . . . ?
N4 C5 C6 C7 -48.4(3) . . . . ?
C15 C5 C6 C7 -170.24(19) . . . . ?
N4 C5 C6 C20 -165.6(2) . . . . ?
C15 C5 C6 C20 72.6(3) . . . . ?
C5 C6 C7 N8 69.3(3) . . . . ?
C20 C6 C7 N8 -168.6(2) . . . . ?
C5 C6 C7 C22 -114.3(2) . . . . ?
C20 C6 C7 C22 7.9(3) . . . . ?
C22 C7 N8 N9 1.7(4) . . . . ?
C6 C7 N8 N9 177.50(19) . . . . ?
C7 N8 N9 C10 169.4(2) . . . . ?
N8 N9 C10 N11 -0.8(3) . . . . ?
N8 N9 C10 S2 178.82(14) . . . . ?
C25 S2 C10 N9 -3.1(2) . . . . ?
C25 S2 C10 N11 176.64(18) . . . . ?
N9 C10 N11 C12 -170.4(2) . . . . ?
S2 C10 N11 C12 9.9(3) . . . . ?
C10 N11 C12 C16 -80.5(3) . . . . ?
C10 N11 C12 C13 158.6(2) . . . . ?
N11 C12 C13 C14 -49.7(2) . . . . ?
C16 C12 C13 C14 -171.1(2) . . . . ?
N11 C12 C13 C17 -164.52(18) . . . . ?
C16 C12 C13 C17 74.1(3) . . . . ?
N2 N1 C14 C19 0.6(3) . . . . ?
N2 N1 C14 C13 178.46(16) . . . . ?
C17 C13 C14 N1 -161.08(19) . . . . ?
C12 C13 C14 N1 78.2(2) . . . . ?
C17 C13 C14 C19 17.1(2) . . . . ?
C12 C13 C14 C19 -103.6(2) . . . . ?
C14 C13 C17 C18 -31.5(2) . . . . ?
C12 C13 C17 C18 90.2(2) . . . . ?
C13 C17 C18 C19 35.2(2) . . . . ?
N1 C14 C19 C18 -178.0(2) . . . . ?
C13 C14 C19 C18 4.0(2) . . . . ?
C17 C18 C19 C14 -23.9(2) . . . . ?
C7 C6 C20 C21 -15.3(3) . . . . ?
C5 C6 C20 C21 109.2(3) . . . . ?
C6 C20 C21 C22 18.1(5) . . . . ?
C20 C21 C22 C7 -12.7(5) . . . . ?
N8 C7 C22 C21 178.3(3) . . . . ?
C6 C7 C22 C21 2.1(4) . . . . ?
C3 S1 C23 C24 -76.4(3) . . . . ?
C10 S2 C25 C26 -167.1(3) . . . . ?
