# Supplementary Information (SI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_vlar141020
_database_code_depnum_ccdc_archive 'CCDC 2324332'
loop_
_audit_author_name
_audit_author_address
'Vladimir Arion'
;Institute of Inorganic Chemistry of the University of Vienna
Austria
;
_audit_update_record             
;
2024-01-09 deposited with the CCDC.	2024-08-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H26 N6 S2'
_chemical_formula_sum            'C16 H26 N6 S2'
_chemical_formula_weight         366.55

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.0619(9)
_cell_length_b                   9.7583(3)
_cell_length_c                   21.8947(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3645.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9949
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      30.06

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_F_000             1568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.303
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6627
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            67173
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.387
_diffrn_reflns_theta_max         30.125
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             5138
_reflns_number_gt                4602
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'SAINT v8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT v8.38A (Bruker, 2018)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0360P)²+1.7274P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5138
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0282
_refine_ls_wR_factor_ref         0.0758
_refine_ls_wR_factor_gt          0.0739
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.47595(2) 0.82870(2) 0.55698(2) 0.01143(6) Uani 1 1 d . . . . .
S2 S 0.13628(2) 0.89697(3) 0.32955(2) 0.01792(7) Uani 1 1 d . . . . .
N1 N 0.41801(5) 0.77653(8) 0.38500(3) 0.01213(16) Uani 1 1 d . . . . .
N2 N 0.45059(5) 0.83378(8) 0.43703(3) 0.01205(16) Uani 1 1 d . . . . .
H2 H 0.4788 0.9092 0.4353 0.014 Uiso 1 1 calc R U . . .
C3 C 0.43710(6) 0.76800(9) 0.49111(4) 0.01003(17) Uani 1 1 d . . . . .
N4 N 0.39300(5) 0.65567(8) 0.48778(3) 0.01065(16) Uani 1 1 d . . . . .
H4 H 0.3796 0.6269 0.4511 0.013 Uiso 1 1 calc R U . . .
C5 C 0.36486(6) 0.57583(9) 0.54017(4) 0.01031(17) Uani 1 1 d . . . . .
H5 H 0.3500 0.6403 0.5737 0.012 Uiso 1 1 calc R U . . .
C6 C 0.29092(6) 0.49629(9) 0.51946(4) 0.01029(17) Uani 1 1 d . . . . .
H6 H 0.3062 0.4225 0.4901 0.012 Uiso 1 1 calc R U . . .
C7 C 0.22859(6) 0.58699(9) 0.49090(4) 0.01028(17) Uani 1 1 d . . . . .
N8 N 0.23750(5) 0.62868(8) 0.43587(3) 0.01170(16) Uani 1 1 d . . . . .
N9 N 0.18094(5) 0.71324(9) 0.41097(4) 0.01319(16) Uani 1 1 d . . . . .
H9 H 0.1357 0.7263 0.4294 0.016 Uiso 1 1 calc R U . . .
C10 C 0.19778(6) 0.77604(9) 0.35644(4) 0.01203(18) Uani 1 1 d . . . . .
N11 N 0.26355(5) 0.73388(9) 0.32985(3) 0.01274(16) Uani 1 1 d . . . . .
H11 H 0.2889 0.6661 0.3475 0.015 Uiso 1 1 calc R U . . .
C12 C 0.29751(6) 0.78979(10) 0.27395(4) 0.01290(18) Uani 1 1 d . . . . .
H12 H 0.2825 0.8885 0.2701 0.015 Uiso 1 1 calc R U . . .
C13 C 0.38765(6) 0.77815(10) 0.27725(4) 0.01257(18) Uani 1 1 d . . . . .
H13 H 0.4034 0.6796 0.2748 0.015 Uiso 1 1 calc R U . . .
C14 C 0.42200(6) 0.84219(10) 0.33459(4) 0.01159(18) Uani 1 1 d . . . . .
C15 C 0.42870(6) 0.47914(10) 0.56356(4) 0.01429(19) Uani 1 1 d . . . . .
H15A H 0.4430 0.4144 0.5312 0.021 Uiso 1 1 calc R U . . .
H15B H 0.4091 0.4285 0.5991 0.021 Uiso 1 1 calc R U . . .
H15C H 0.4749 0.5326 0.5754 0.021 Uiso 1 1 calc R U . . .
C16 C 0.26603(7) 0.71060(12) 0.21896(4) 0.0199(2) Uani 1 1 d . . . . .
H16A H 0.2772 0.6128 0.2241 0.030 Uiso 1 1 calc R U . . .
H16B H 0.2914 0.7439 0.1817 0.030 Uiso 1 1 calc R U . . .
H16C H 0.2093 0.7243 0.2158 0.030 Uiso 1 1 calc R U . . .
C17 C 0.24640(6) 0.43318(10) 0.57383(4) 0.01415(18) Uani 1 1 d . . . . .
H17A H 0.2174 0.3501 0.5611 0.017 Uiso 1 1 calc R U . . .
H17B H 0.2830 0.4085 0.6072 0.017 Uiso 1 1 calc R U . . .
C18 C 0.18958(6) 0.54614(10) 0.59447(4) 0.01481(19) Uani 1 1 d . . . . .
H18A H 0.1452 0.5071 0.6178 0.018 Uiso 1 1 calc R U . . .
H18B H 0.2167 0.6148 0.6202 0.018 Uiso 1 1 calc R U . . .
C19 C 0.16131(6) 0.61023(10) 0.53432(4) 0.01289(18) Uani 1 1 d . . . . .
H19A H 0.1131 0.5645 0.5195 0.015 Uiso 1 1 calc R U . . .
H19B H 0.1507 0.7093 0.5394 0.015 Uiso 1 1 calc R U . . .
C20 C 0.42884(7) 0.85982(11) 0.22620(4) 0.0184(2) Uani 1 1 d . . . . .
H20A H 0.4804 0.8189 0.2162 0.022 Uiso 1 1 calc R U . . .
H20B H 0.3963 0.8622 0.1888 0.022 Uiso 1 1 calc R U . . .
C21 C 0.43877(7) 1.00413(11) 0.25292(5) 0.0189(2) Uani 1 1 d . . . . .
H21A H 0.3896 1.0574 0.2493 0.023 Uiso 1 1 calc R U . . .
H21B H 0.4813 1.0543 0.2318 0.023 Uiso 1 1 calc R U . . .
C22 C 0.45962(7) 0.97894(10) 0.32043(4) 0.0168(2) Uani 1 1 d . . . . .
H22A H 0.5171 0.9748 0.3262 0.020 Uiso 1 1 calc R U . . .
H22B H 0.4379 1.0521 0.3468 0.020 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 1.6943(9) . ?
S2 C10 1.6853(10) . ?
N1 C14 1.2780(12) . ?
N1 N2 1.3853(11) . ?
N2 C3 1.3662(11) . ?
N2 H2 0.8800 . ?
C3 N4 1.3316(12) . ?
N4 C5 1.4673(11) . ?
N4 H4 0.8800 . ?
C5 C15 1.5294(13) . ?
C5 C6 1.5491(13) . ?
C5 H5 1.0000 . ?
C6 C7 1.5183(13) . ?
C6 C17 1.5406(13) . ?
C6 H6 1.0000 . ?
C7 N8 1.2806(11) . ?
C7 C19 1.5076(13) . ?
N8 N9 1.3818(12) . ?
N9 C10 1.3723(12) . ?
N9 H9 0.8800 . ?
C10 N11 1.3294(13) . ?
N11 C12 1.4599(11) . ?
N11 H11 0.8800 . ?
C12 C16 1.5281(13) . ?
C12 C13 1.5439(15) . ?
C12 H12 1.0000 . ?
C13 C14 1.5199(13) . ?
C13 C20 1.5422(13) . ?
C13 H13 1.0000 . ?
C14 C22 1.5129(13) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.5359(14) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.5356(13) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.5343(15) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.5402(13) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?

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
C14 N1 N2 119.13(8) . . ?
C3 N2 N1 117.10(8) . . ?
C3 N2 H2 121.4 . . ?
N1 N2 H2 121.4 . . ?
N4 C3 N2 115.76(8) . . ?
N4 C3 S1 123.74(7) . . ?
N2 C3 S1 120.50(7) . . ?
C3 N4 C5 125.40(8) . . ?
C3 N4 H4 117.3 . . ?
C5 N4 H4 117.3 . . ?
N4 C5 C15 110.87(8) . . ?
N4 C5 C6 107.68(7) . . ?
C15 C5 C6 111.65(8) . . ?
N4 C5 H5 108.9 . . ?
C15 C5 H5 108.9 . . ?
C6 C5 H5 108.9 . . ?
C7 C6 C17 101.88(8) . . ?
C7 C6 C5 113.51(7) . . ?
C17 C6 C5 112.07(7) . . ?
C7 C6 H6 109.7 . . ?
C17 C6 H6 109.7 . . ?
C5 C6 H6 109.7 . . ?
N8 C7 C19 129.48(9) . . ?
N8 C7 C6 119.30(9) . . ?
C19 C7 C6 111.18(7) . . ?
C7 N8 N9 118.56(8) . . ?
C10 N9 N8 117.63(8) . . ?
C10 N9 H9 121.2 . . ?
N8 N9 H9 121.2 . . ?
N11 C10 N9 114.80(8) . . ?
N11 C10 S2 126.10(7) . . ?
N9 C10 S2 119.10(8) . . ?
C10 N11 C12 125.91(8) . . ?
C10 N11 H11 117.0 . . ?
C12 N11 H11 117.0 . . ?
N11 C12 C16 109.39(8) . . ?
N11 C12 C13 109.19(8) . . ?
C16 C12 C13 110.47(8) . . ?
N11 C12 H12 109.3 . . ?
C16 C12 H12 109.3 . . ?
C13 C12 H12 109.3 . . ?
C14 C13 C20 102.15(8) . . ?
C14 C13 C12 113.11(8) . . ?
C20 C13 C12 112.46(8) . . ?
C14 C13 H13 109.6 . . ?
C20 C13 H13 109.6 . . ?
C12 C13 H13 109.6 . . ?
N1 C14 C22 129.92(9) . . ?
N1 C14 C13 119.13(8) . . ?
C22 C14 C13 110.92(8) . . ?
C5 C15 H15A 109.5 . . ?
C5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C6 104.57(7) . . ?
C18 C17 H17A 110.8 . . ?
C6 C17 H17A 110.8 . . ?
C18 C17 H17B 110.8 . . ?
C6 C17 H17B 110.8 . . ?
H17A C17 H17B 108.9 . . ?
C19 C18 C17 103.78(7) . . ?
C19 C18 H18A 111.0 . . ?
C17 C18 H18A 111.0 . . ?
C19 C18 H18B 111.0 . . ?
C17 C18 H18B 111.0 . . ?
H18A C18 H18B 109.0 . . ?
C7 C19 C18 103.91(8) . . ?
C7 C19 H19A 111.0 . . ?
C18 C19 H19A 111.0 . . ?
C7 C19 H19B 111.0 . . ?
C18 C19 H19B 111.0 . . ?
H19A C19 H19B 109.0 . . ?
C21 C20 C13 104.38(8) . . ?
C21 C20 H20A 110.9 . . ?
C13 C20 H20A 110.9 . . ?
C21 C20 H20B 110.9 . . ?
C13 C20 H20B 110.9 . . ?
H20A C20 H20B 108.9 . . ?
C20 C21 C22 104.18(8) . . ?
C20 C21 H21A 110.9 . . ?
C22 C21 H21A 110.9 . . ?
C20 C21 H21B 110.9 . . ?
C22 C21 H21B 110.9 . . ?
H21A C21 H21B 108.9 . . ?
C14 C22 C21 103.85(8) . . ?
C14 C22 H22A 111.0 . . ?
C21 C22 H22A 111.0 . . ?
C14 C22 H22B 111.0 . . ?
C21 C22 H22B 111.0 . . ?
H22A C22 H22B 109.0 . . ?

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 172.58(9) . . . . ?
N1 N2 C3 N4 -0.62(13) . . . . ?
N1 N2 C3 S1 178.87(7) . . . . ?
N2 C3 N4 C5 -174.05(9) . . . . ?
S1 C3 N4 C5 6.47(14) . . . . ?
C3 N4 C5 C15 -80.99(11) . . . . ?
C3 N4 C5 C6 156.60(9) . . . . ?
N4 C5 C6 C7 -53.20(10) . . . . ?
C15 C5 C6 C7 -175.13(7) . . . . ?
N4 C5 C6 C17 -167.95(8) . . . . ?
C15 C5 C6 C17 70.12(10) . . . . ?
C17 C6 C7 N8 -162.02(8) . . . . ?
C5 C6 C7 N8 77.30(10) . . . . ?
C17 C6 C7 C19 16.04(10) . . . . ?
C5 C6 C7 C19 -104.63(9) . . . . ?
C19 C7 N8 N9 3.53(15) . . . . ?
C6 C7 N8 N9 -178.81(8) . . . . ?
C7 N8 N9 C10 168.81(9) . . . . ?
N8 N9 C10 N11 8.24(12) . . . . ?
N8 N9 C10 S2 -171.31(7) . . . . ?
N9 C10 N11 C12 -175.76(9) . . . . ?
S2 C10 N11 C12 3.75(14) . . . . ?
C10 N11 C12 C16 -90.76(11) . . . . ?
C10 N11 C12 C13 148.23(9) . . . . ?
N11 C12 C13 C14 -53.66(10) . . . . ?
C16 C12 C13 C14 -174.00(8) . . . . ?
N11 C12 C13 C20 -168.75(8) . . . . ?
C16 C12 C13 C20 70.91(10) . . . . ?
N2 N1 C14 C22 1.29(17) . . . . ?
N2 N1 C14 C13 178.82(9) . . . . ?
C20 C13 C14 N1 -160.87(10) . . . . ?
C12 C13 C14 N1 78.01(12) . . . . ?
C20 C13 C14 C22 17.10(11) . . . . ?
C12 C13 C14 C22 -104.02(10) . . . . ?
C7 C6 C17 C18 -33.35(9) . . . . ?
C5 C6 C17 C18 88.33(9) . . . . ?
C6 C17 C18 C19 38.99(10) . . . . ?
N8 C7 C19 C18 -174.73(10) . . . . ?
C6 C7 C19 C18 7.46(10) . . . . ?
C17 C18 C19 C7 -28.13(10) . . . . ?
C14 C13 C20 C21 -33.77(10) . . . . ?
C12 C13 C20 C21 87.79(10) . . . . ?
C13 C20 C21 C22 38.63(11) . . . . ?
N1 C14 C22 C21 -176.15(11) . . . . ?
C13 C14 C22 C21 6.16(12) . . . . ?
C20 C21 C22 C14 -27.24(11) . . . . ?

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
N2 H2 S1 0.88 2.68 3.5265(8) 162.6 5_676
N4 H4 N8 0.88 2.45 2.8983(12) 112.3 .
C6 H6 N9 1.00 2.69 3.6746(12) 169.5 7_655
N9 H9 S1 0.88 2.79 3.5907(9) 151.2 3_466
N11 H11 S2 0.88 2.95 3.7055(9) 145.5 7_655
C15 H15C S1 0.98 2.92 3.5081(10) 119.7 .
C19 H19A S1 0.99 2.88 3.6439(10) 134.9 7_655
C22 H22B S1 0.99 2.82 3.4547(10) 122.6 5_676

_refine_diff_density_max         0.381
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.051

_shelxl_version_number           2014-3



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_iubem3
_database_code_depnum_ccdc_archive 'CCDC 2324333'
loop_
_audit_author_name
_audit_author_address
'Vladimir Arion'
;Institute of Inorganic Chemistry of the University of Vienna
Austria
;
_audit_update_record             
;
2024-01-09 deposited with the CCDC.	2024-08-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H34 N6 S2'
_chemical_formula_sum            'C20 H34 N6 S2'
_chemical_formula_weight         422.65

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2324(7)
_cell_length_b                   10.4294(7)
_cell_length_c                   12.5483(8)
_cell_angle_alpha                101.269(5)
_cell_angle_beta                 103.562(6)
_cell_angle_gamma                93.900(6)
_cell_volume                     1143.68(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    11890
_cell_measurement_theta_min      3.63
_cell_measurement_theta_max      71.78

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    2.238
_shelx_estimated_absorpt_T_min   0.760
_shelx_estimated_absorpt_T_max   0.791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7266
_exptl_absorpt_correction_T_max  0.7870
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23743
_diffrn_reflns_av_unetI/netI     0.0111
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.713
_diffrn_reflns_theta_max         71.455
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measured_fraction_theta_full 0.944
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_Laue_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_point_group_measured_fraction_full 0.944
_reflns_number_total             4154
_reflns_number_gt                3510
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
X-Area Pilatus3_SV 1.31.170.0 (STOE, 2020)
;
_computing_cell_refinement       
;
X-Area Recipe 1.36.0.0 (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
;

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0766P)²+0.4731P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4154
_refine_ls_number_parameters     257
_refine_ls_number_restraints     468
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1456
_refine_ls_wR_factor_gt          0.1389
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.162
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_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_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) . . . . ?

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 .

_refine_diff_density_max         0.492
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.044

_shelxl_version_number           2014-3



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_vlar2910
_database_code_depnum_ccdc_archive 'CCDC 2324334'
loop_
_audit_author_name
_audit_author_address
'Vladimir Arion'
;Institute of Inorganic Chemistry of the University of Vienna
Austria
;
_audit_update_record             
;
2024-01-09 deposited with the CCDC.	2024-08-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H24 N6 Ni S2'
_chemical_formula_sum            'C16 H24 N6 Ni S2'
_chemical_formula_weight         423.24

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'
Ni Ni 0.3393 1.1124 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   17.4292(5)
_cell_length_b                   6.6235(3)
_cell_length_c                   16.2981(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.416(2)
_cell_angle_gamma                90
_cell_volume                     1850.48(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9910
_cell_measurement_theta_min      3.151
_cell_measurement_theta_max      29.896

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.241
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.071
_exptl_absorpt_coefficient_mu    1.286
_shelx_estimated_absorpt_T_min   0.747
_shelx_estimated_absorpt_T_max   0.914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7468
_exptl_absorpt_correction_T_max  0.9142
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20265
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.376
_diffrn_reflns_theta_max         30.068
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5434
_reflns_number_gt                4873
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.999
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'SAINT v8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT v8.38A (Bruker, 2018)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0352P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.477(12)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5434
_refine_ls_number_parameters     229
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.0679
_refine_ls_wR_factor_gt          0.0661
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Ni Ni 0.61869(2) 0.88765(5) 0.82491(2) 0.01310(9) Uani 1 1 d . . . . .
S1 S 0.77962(4) 1.34053(13) 0.75965(5) 0.02050(17) Uani 1 1 d . . . . .
S2 S 0.44802(4) 0.63889(13) 0.96106(5) 0.01944(17) Uani 1 1 d . . . . .
N1 N 0.71962(15) 0.8831(4) 0.88521(17) 0.0133(5) Uani 1 1 d . . . . .
N2 N 0.75999(15) 1.0563(4) 0.86938(16) 0.0171(5) Uani 1 1 d . . . . .
H2 H 0.8016 1.1010 0.9033 0.021 Uiso 1 1 calc R U . . .
N4 N 0.65849(15) 1.0840(4) 0.76221(15) 0.0145(5) Uani 1 1 d . . . . .
N8 N 0.51453(14) 0.9555(4) 0.78449(15) 0.0131(5) Uani 1 1 d . . . . .
N9 N 0.46869(15) 0.8847(4) 0.84039(16) 0.0157(5) Uani 1 1 d . . . . .
H9 H 0.4211 0.9289 0.8404 0.019 Uiso 1 1 calc R U . . .
N11 N 0.57751(14) 0.7046(4) 0.89304(14) 0.0125(5) Uani 1 1 d . . . . .
C3 C 0.72831(17) 1.1520(5) 0.79482(19) 0.0151(6) Uani 1 1 d . . . . .
C5 C 0.61844(17) 1.1532(5) 0.67992(17) 0.0149(6) Uani 1 1 d . . . . .
H5 H 0.6455 1.2777 0.6653 0.018 Uiso 1 1 calc R U . . .
C6 C 0.53274(17) 1.2055(5) 0.67758(17) 0.0134(6) Uani 1 1 d . . . . .
H6 H 0.5048 1.1645 0.6210 0.016 Uiso 1 1 calc R U . . .
C7 C 0.48904(17) 1.1073(4) 0.73881(18) 0.0135(6) Uani 1 1 d . . . . .
C10 C 0.50393(17) 0.7399(5) 0.89558(17) 0.0150(6) Uani 1 1 d . . . . .
C12 C 0.62047(17) 0.5574(5) 0.95229(17) 0.0144(6) Uani 1 1 d . . . . .
H12 H 0.6113 0.5906 1.0096 0.017 Uiso 1 1 calc R U . . .
C13 C 0.70828(17) 0.5608(5) 0.95296(18) 0.0149(6) Uani 1 1 d . . . . .
H13 H 0.7179 0.4727 0.9060 0.018 Uiso 1 1 calc R U . . .
C14 C 0.74757(16) 0.7603(5) 0.94357(17) 0.0143(6) Uani 1 1 d . . . . .
C15 C 0.6273(2) 0.9899(6) 0.6154(2) 0.0247(7) Uani 1 1 d . . . . .
H15A H 0.6030 0.8644 0.6297 0.037 Uiso 1 1 calc R U . . .
H15B H 0.6829 0.9662 0.6156 0.037 Uiso 1 1 calc R U . . .
H15C H 0.6019 1.0349 0.5599 0.037 Uiso 1 1 calc R U . . .
C16 C 0.5922(2) 0.3412(5) 0.9309(2) 0.0219(7) Uani 1 1 d . . . . .
H16A H 0.5983 0.3089 0.8738 0.033 Uiso 1 1 calc R U . . .
H16B H 0.5371 0.3298 0.9356 0.033 Uiso 1 1 calc R U . . .
H16C H 0.6231 0.2466 0.9698 0.033 Uiso 1 1 calc R U . . .
C17 C 0.51237(19) 1.4288(5) 0.68726(19) 0.0175(6) Uani 1 1 d . . . . .
H17A H 0.5436 1.4874 0.7385 0.021 Uiso 1 1 calc R U . . .
H17B H 0.5210 1.5089 0.6385 0.021 Uiso 1 1 calc R U . . .
C18 C 0.4258(2) 1.4205(5) 0.6928(2) 0.0216(7) Uani 1 1 d . . . . .
H18A H 0.3932 1.4080 0.6366 0.026 Uiso 1 1 calc R U . . .
H18B H 0.4100 1.5432 0.7201 0.026 Uiso 1 1 calc R U . . .
C19 C 0.41812(17) 1.2310(5) 0.74580(19) 0.0174(6) Uani 1 1 d . . . . .
H19A H 0.4178 1.2680 0.8046 0.021 Uiso 1 1 calc R U . . .
H19B H 0.3697 1.1561 0.7235 0.021 Uiso 1 1 calc R U . . .
C20 C 0.75693(19) 0.4731(5) 1.0339(2) 0.0219(7) Uani 1 1 d . . . . .
H20A H 0.7337 0.5102 1.0829 0.026 Uiso 1 1 calc R U . . .
H20B H 0.7598 0.3241 1.0306 0.026 Uiso 1 1 calc R U . . .
C21 C 0.83788(19) 0.5673(6) 1.0398(2) 0.0236(7) Uani 1 1 d . . . . .
H21A H 0.8654 0.5726 1.0985 0.028 Uiso 1 1 calc R U . . .
H21B H 0.8699 0.4891 1.0067 0.028 Uiso 1 1 calc R U . . .
C22 C 0.8223(2) 0.7783(6) 1.0046(2) 0.0280(8) Uani 1 1 d . . . . .
H22A H 0.8170 0.8756 1.0493 0.034 Uiso 1 1 calc R U . . .
H22B H 0.8651 0.8234 0.9765 0.034 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Ni N1 1.854(3) . ?
Ni N4 1.863(3) . ?
Ni N8 1.871(2) . ?
Ni N11 1.873(3) . ?
S1 C3 1.695(3) . ?
S2 C10 1.707(3) . ?
N1 C14 1.279(4) . ?
N1 N2 1.394(4) . ?
N2 C3 1.393(4) . ?
N2 H2 0.8800 . ?
N4 C3 1.316(4) . ?
N4 C5 1.469(4) . ?
N8 C7 1.282(4) . ?
N8 N9 1.397(3) . ?
N9 C10 1.381(4) . ?
N9 H9 0.8800 . ?
N11 C10 1.312(4) . ?
N11 C12 1.477(4) . ?
C5 C6 1.527(4) . ?
C5 C15 1.536(5) . ?
C5 H5 1.0000 . ?
C6 C7 1.508(4) . ?
C6 C17 1.536(4) . ?
C6 H6 1.0000 . ?
C7 C19 1.504(4) . ?
C12 C13 1.529(4) . ?
C12 C16 1.534(5) . ?
C12 H12 1.0000 . ?
C13 C14 1.509(4) . ?
C13 C20 1.546(4) . ?
C13 H13 1.0000 . ?
C14 C22 1.494(4) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.528(5) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.543(5) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.530(5) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.516(5) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?

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
N1 Ni N4 83.71(11) . . ?
N1 Ni N8 163.36(12) . . ?
N4 Ni N8 94.19(11) . . ?
N1 Ni N11 95.96(11) . . ?
N4 Ni N11 176.02(12) . . ?
N8 Ni N11 85.00(11) . . ?
C14 N1 N2 121.6(3) . . ?
C14 N1 Ni 127.0(2) . . ?
N2 N1 Ni 110.54(18) . . ?
C3 N2 N1 113.7(2) . . ?
C3 N2 H2 123.1 . . ?
N1 N2 H2 123.1 . . ?
C3 N4 C5 120.9(3) . . ?
C3 N4 Ni 115.2(2) . . ?
C5 N4 Ni 123.8(2) . . ?
C7 N8 N9 117.6(3) . . ?
C7 N8 Ni 127.3(2) . . ?
N9 N8 Ni 108.83(18) . . ?
C10 N9 N8 114.7(2) . . ?
C10 N9 H9 122.6 . . ?
N8 N9 H9 122.6 . . ?
C10 N11 C12 118.7(2) . . ?
C10 N11 Ni 112.6(2) . . ?
C12 N11 Ni 127.71(19) . . ?
N4 C3 N2 112.8(3) . . ?
N4 C3 S1 128.4(2) . . ?
N2 C3 S1 118.7(2) . . ?
N4 C5 C6 113.3(2) . . ?
N4 C5 C15 108.4(3) . . ?
C6 C5 C15 111.2(2) . . ?
N4 C5 H5 107.9 . . ?
C6 C5 H5 107.9 . . ?
C15 C5 H5 107.9 . . ?
C7 C6 C5 119.6(2) . . ?
C7 C6 C17 101.2(2) . . ?
C5 C6 C17 117.3(2) . . ?
C7 C6 H6 105.8 . . ?
C5 C6 H6 105.8 . . ?
C17 C6 H6 105.8 . . ?
N8 C7 C19 125.9(3) . . ?
N8 C7 C6 124.0(3) . . ?
C19 C7 C6 109.6(2) . . ?
N11 C10 N9 115.2(3) . . ?
N11 C10 S2 128.5(2) . . ?
N9 C10 S2 116.3(2) . . ?
N11 C12 C13 112.6(2) . . ?
N11 C12 C16 111.3(2) . . ?
C13 C12 C16 107.2(3) . . ?
N11 C12 H12 108.6 . . ?
C13 C12 H12 108.6 . . ?
C16 C12 H12 108.6 . . ?
C14 C13 C12 119.0(3) . . ?
C14 C13 C20 103.1(2) . . ?
C12 C13 C20 113.2(2) . . ?
C14 C13 H13 107.0 . . ?
C12 C13 H13 107.0 . . ?
C20 C13 H13 107.0 . . ?
N1 C14 C22 127.8(3) . . ?
N1 C14 C13 120.9(3) . . ?
C22 C14 C13 111.1(2) . . ?
C5 C15 H15A 109.5 . . ?
C5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C6 102.7(3) . . ?
C18 C17 H17A 111.2 . . ?
C6 C17 H17A 111.2 . . ?
C18 C17 H17B 111.2 . . ?
C6 C17 H17B 111.2 . . ?
H17A C17 H17B 109.1 . . ?
C17 C18 C19 104.4(2) . . ?
C17 C18 H18A 110.9 . . ?
C19 C18 H18A 110.9 . . ?
C17 C18 H18B 110.9 . . ?
C19 C18 H18B 110.9 . . ?
H18A C18 H18B 108.9 . . ?
C7 C19 C18 104.2(2) . . ?
C7 C19 H19A 110.9 . . ?
C18 C19 H19A 110.9 . . ?
C7 C19 H19B 110.9 . . ?
C18 C19 H19B 110.9 . . ?
H19A C19 H19B 108.9 . . ?
C21 C20 C13 105.0(3) . . ?
C21 C20 H20A 110.8 . . ?
C13 C20 H20A 110.8 . . ?
C21 C20 H20B 110.8 . . ?
C13 C20 H20B 110.8 . . ?
H20A C20 H20B 108.8 . . ?
C22 C21 C20 104.6(3) . . ?
C22 C21 H21A 110.8 . . ?
C20 C21 H21A 110.8 . . ?
C22 C21 H21B 110.8 . . ?
C20 C21 H21B 110.8 . . ?
H21A C21 H21B 108.9 . . ?
C14 C22 C21 104.7(3) . . ?
C14 C22 H22A 110.8 . . ?
C21 C22 H22A 110.8 . . ?
C14 C22 H22B 110.8 . . ?
C21 C22 H22B 110.8 . . ?
H22A C22 H22B 108.9 . . ?

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
N4 Ni N1 C14 -173.1(3) . . . . ?
N8 Ni N1 C14 103.3(4) . . . . ?
N11 Ni N1 C14 10.9(3) . . . . ?
N4 Ni N1 N2 17.5(2) . . . . ?
N8 Ni N1 N2 -66.0(5) . . . . ?
N11 Ni N1 N2 -158.5(2) . . . . ?
C14 N1 N2 C3 168.8(3) . . . . ?
Ni N1 N2 C3 -21.2(3) . . . . ?
N1 Ni N4 C3 -11.5(2) . . . . ?
N8 Ni N4 C3 152.0(2) . . . . ?
N1 Ni N4 C5 165.2(2) . . . . ?
N8 Ni N4 C5 -31.4(2) . . . . ?
N1 Ni N8 C7 73.9(5) . . . . ?
N4 Ni N8 C7 -8.1(3) . . . . ?
N11 Ni N8 C7 167.9(3) . . . . ?
N1 Ni N8 N9 -77.1(5) . . . . ?
N4 Ni N8 N9 -159.1(2) . . . . ?
N11 Ni N8 N9 17.0(2) . . . . ?
C7 N8 N9 C10 -171.5(3) . . . . ?
Ni N8 N9 C10 -17.4(3) . . . . ?
N1 Ni N11 C10 148.9(2) . . . . ?
N8 Ni N11 C10 -14.4(2) . . . . ?
N1 Ni N11 C12 -19.6(2) . . . . ?
N8 Ni N11 C12 177.1(2) . . . . ?
C5 N4 C3 N2 -174.5(3) . . . . ?
Ni N4 C3 N2 2.3(3) . . . . ?
C5 N4 C3 S1 8.1(4) . . . . ?
Ni N4 C3 S1 -175.09(19) . . . . ?
N1 N2 C3 N4 12.5(4) . . . . ?
N1 N2 C3 S1 -169.9(2) . . . . ?
C3 N4 C5 C6 -135.1(3) . . . . ?
Ni N4 C5 C6 48.4(3) . . . . ?
C3 N4 C5 C15 101.0(3) . . . . ?
Ni N4 C5 C15 -75.5(3) . . . . ?
N4 C5 C6 C7 -25.5(4) . . . . ?
C15 C5 C6 C7 96.8(3) . . . . ?
N4 C5 C6 C17 97.5(3) . . . . ?
C15 C5 C6 C17 -140.2(3) . . . . ?
N9 N8 C7 C19 6.8(4) . . . . ?
Ni N8 C7 C19 -141.9(3) . . . . ?
N9 N8 C7 C6 178.0(3) . . . . ?
Ni N8 C7 C6 29.2(4) . . . . ?
C5 C6 C7 N8 -12.4(4) . . . . ?
C17 C6 C7 N8 -143.0(3) . . . . ?
C5 C6 C7 C19 159.9(3) . . . . ?
C17 C6 C7 C19 29.3(3) . . . . ?
C12 N11 C10 N9 177.7(3) . . . . ?
Ni N11 C10 N9 8.0(3) . . . . ?
C12 N11 C10 S2 1.0(4) . . . . ?
Ni N11 C10 S2 -168.69(19) . . . . ?
N8 N9 C10 N11 6.4(4) . . . . ?
N8 N9 C10 S2 -176.4(2) . . . . ?
C10 N11 C12 C13 -169.4(3) . . . . ?
Ni N11 C12 C13 -1.5(4) . . . . ?
C10 N11 C12 C16 70.2(3) . . . . ?
Ni N11 C12 C16 -121.9(3) . . . . ?
N11 C12 C13 C14 37.1(4) . . . . ?
C16 C12 C13 C14 159.9(2) . . . . ?
N11 C12 C13 C20 158.4(3) . . . . ?
C16 C12 C13 C20 -78.9(3) . . . . ?
N2 N1 C14 C22 2.3(5) . . . . ?
Ni N1 C14 C22 -166.1(3) . . . . ?
N2 N1 C14 C13 -172.1(3) . . . . ?
Ni N1 C14 C13 19.6(4) . . . . ?
C12 C13 C14 N1 -49.2(4) . . . . ?
C20 C13 C14 N1 -175.4(3) . . . . ?
C12 C13 C14 C22 135.6(3) . . . . ?
C20 C13 C14 C22 9.3(3) . . . . ?
C7 C6 C17 C18 -41.3(3) . . . . ?
C5 C6 C17 C18 -173.3(2) . . . . ?
C6 C17 C18 C19 38.9(3) . . . . ?
N8 C7 C19 C18 166.4(3) . . . . ?
C6 C7 C19 C18 -5.7(3) . . . . ?
C17 C18 C19 C7 -20.6(3) . . . . ?
C14 C13 C20 C21 -26.8(3) . . . . ?
C12 C13 C20 C21 -156.7(3) . . . . ?
C13 C20 C21 C22 34.9(4) . . . . ?
N1 C14 C22 C21 -162.9(3) . . . . ?
C13 C14 C22 C21 12.0(4) . . . . ?
C20 C21 C22 C14 -28.6(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
N2 H2 S2 0.88 2.57 3.392(3) 156.2 3
N9 H9 S1 0.88 2.64 3.333(3) 136.1 3_445
C5 H5 S1 1.00 2.59 3.131(3) 113.9 .
C6 H6 S2 1.00 2.92 3.716(3) 137.0 2_574
C13 H13 S1 1.00 2.92 3.875(3) 159.4 1_545
C16 H16B S2 0.98 2.65 3.300(4) 124.3 .
C19 H19B S1 0.99 2.74 3.573(3) 141.9 3_445
C22 H22B S2 0.99 2.58 3.402(4) 140.6 3

_refine_diff_density_max         0.299
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.063

_shelxl_version_number           2014-3



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_iube031b
_database_code_depnum_ccdc_archive 'CCDC 2324335'
loop_
_audit_author_name
_audit_author_address
'Vladimir Arion'
;Institute of Inorganic Chemistry of the University of Vienna
Austria
;
_audit_update_record             
;
2024-01-09 deposited with the CCDC.	2024-08-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H28 N6 Ni S2'
_chemical_formula_sum            'C18 H28 N6 Ni S2'
_chemical_formula_weight         451.29

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'
Ni Ni 0.3393 1.1124 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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'

_cell_length_a                   11.5410(2)
_cell_length_b                   13.7657(2)
_cell_length_c                   13.0159(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.9050(10)
_cell_angle_gamma                90
_cell_volume                     2007.24(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9324
_cell_measurement_theta_min      2.188
_cell_measurement_theta_max      30.060

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.312
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.143
_exptl_absorpt_coefficient_mu    1.191
_shelx_estimated_absorpt_T_min   0.708
_shelx_estimated_absorpt_T_max   0.848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5240
_exptl_absorpt_correction_T_max  0.5642
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            74695
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.818
_diffrn_reflns_theta_max         30.079
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5901
_reflns_number_gt                5175
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT V8.38A'
_computing_data_reduction        'Bruker SAINT V8.38A'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0284P)²+1.0806P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5901
_refine_ls_number_parameters     267
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0254
_refine_ls_wR_factor_ref         0.0639
_refine_ls_wR_factor_gt          0.0620
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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 0.74044(2) 0.09459(2) 0.42442(2) 0.01474(5) Uani 1 1 d . . . . .
S1 S 0.52967(3) -0.03599(3) 0.13852(3) 0.02762(8) Uani 1 1 d . . . . .
N1 N 0.57700(9) 0.09245(7) 0.40820(8) 0.0175(2) Uani 1 1 d . . . . .
S2 S 0.91001(3) 0.35972(2) 0.56811(3) 0.02557(8) Uani 1 1 d . . . . .
N2 N 0.51174(10) 0.05058(8) 0.31388(8) 0.0192(2) Uani 1 1 d . . . . .
C3 C 0.58948(11) 0.00829(9) 0.26824(9) 0.0184(2) Uani 1 1 d . . . . .
N4 N 0.70666(9) 0.00204(8) 0.31457(8) 0.01682(19) Uani 1 1 d . . . . .
C5 C 0.79038(11) -0.04346(9) 0.25993(10) 0.0188(2) Uani 1 1 d . . . . .
H5 H 0.7817 -0.0110 0.1898 0.023 Uiso 1 1 calc R U . . .
C6 C 0.92026(11) -0.03218(9) 0.32372(9) 0.0182(2) Uani 1 1 d . . . . .
H6 H 0.9329 -0.0788 0.3843 0.022 Uiso 1 1 calc R U . . .
C7 C 0.95907(11) 0.06641(9) 0.36868(9) 0.0174(2) Uani 1 1 d . . . . .
N8 N 0.89714(9) 0.11632(8) 0.41971(8) 0.01639(19) Uani 1 1 d . . . . .
N9 N 0.94630(10) 0.20421(8) 0.46362(8) 0.0190(2) Uani 1 1 d . . . . .
C10 C 0.87061(11) 0.24237(9) 0.51440(9) 0.0181(2) Uani 1 1 d . . . . .
N11 N 0.76996(9) 0.19812(8) 0.52224(8) 0.0176(2) Uani 1 1 d . . . . .
C12 C 0.68925(11) 0.24048(9) 0.58202(10) 0.0204(2) Uani 1 1 d . . . . .
H12 H 0.6644 0.3064 0.5524 0.025 Uiso 1 1 calc R U . . .
C13 C 0.57713(12) 0.17857(11) 0.57255(12) 0.0267(3) Uani 1 1 d . . . . .
H13 H 0.6054 0.1206 0.6180 0.032 Uiso 1 1 calc R U . A 1
C14 C 0.51805(11) 0.13641(9) 0.46630(10) 0.0195(2) Uani 1 1 d . . . . .
C15 C 0.76864(13) -0.15286(10) 0.24137(12) 0.0275(3) Uani 1 1 d . . . . .
H15A H 0.7878 -0.1869 0.3095 0.041 Uiso 1 1 calc R U . . .
H15B H 0.8196 -0.1775 0.1968 0.041 Uiso 1 1 calc R U . . .
H15C H 0.6847 -0.1640 0.2060 0.041 Uiso 1 1 calc R U . . .
C16 C 0.74686(13) 0.25113(12) 0.70081(11) 0.0293(3) Uani 1 1 d . . . . .
H16A H 0.7696 0.1869 0.7315 0.044 Uiso 1 1 calc R U . . .
H16B H 0.6897 0.2811 0.7360 0.044 Uiso 1 1 calc R U . . .
H16C H 0.8181 0.2922 0.7107 0.044 Uiso 1 1 calc R U . . .
C17 C 1.01247(12) -0.05664(10) 0.25926(10) 0.0217(2) Uani 1 1 d . . . . .
H17A H 1.0297 -0.1272 0.2621 0.026 Uiso 1 1 calc R U . . .
H17B H 0.9825 -0.0371 0.1844 0.026 Uiso 1 1 calc R U . . .
C18 C 1.12453(12) 0.00131(10) 0.31155(10) 0.0224(3) Uani 1 1 d . . . . .
H18A H 1.1752 -0.0360 0.3706 0.027 Uiso 1 1 calc R U . . .
H18B H 1.1719 0.0166 0.2595 0.027 Uiso 1 1 calc R U . . .
C19 C 1.07873(12) 0.09459(10) 0.35254(11) 0.0223(3) Uani 1 1 d . . . . .
H19A H 1.1328 0.1158 0.4199 0.027 Uiso 1 1 calc R U . . .
H19B H 1.0713 0.1477 0.3000 0.027 Uiso 1 1 calc R U . . .
C20A C 0.4773(2) 0.2224(2) 0.6192(2) 0.0206(5) Uani 0.6 1 d . . P B 1
H20A H 0.4548 0.1776 0.6706 0.025 Uiso 0.6 1 calc R U P B 1
H20B H 0.5018 0.2855 0.6540 0.025 Uiso 0.6 1 calc R U P B 1
C20B C 0.4694(4) 0.2498(3) 0.5806(4) 0.0228(8) Uani 0.4 1 d . . P B 2
H20C H 0.4718 0.2649 0.6554 0.027 Uiso 0.4 1 calc R U P B 2
H20D H 0.4742 0.3114 0.5424 0.027 Uiso 0.4 1 calc R U P B 2
C21A C 0.3748(2) 0.2348(2) 0.5199(2) 0.0227(5) Uani 0.6 1 d D . P B 1
H21A H 0.3817 0.2980 0.4855 0.027 Uiso 0.6 1 calc R U P B 1
H21B H 0.2968 0.2324 0.5389 0.027 Uiso 0.6 1 calc R U P B 1
C21B C 0.3555(4) 0.1946(3) 0.5292(3) 0.0225(8) Uani 0.4 1 d D . P B 2
H21C H 0.3351 0.1467 0.5789 0.027 Uiso 0.4 1 calc R U P B 2
H21D H 0.2875 0.2396 0.5053 0.027 Uiso 0.4 1 calc R U P B 2
C22 C 0.38558(12) 0.14787(10) 0.44236(12) 0.0259(3) Uani 1 1 d D . . . .
H22C H 0.3577 0.1872 0.3774 0.031 Uiso 0.4 1 calc R U P B 2
H22D H 0.3466 0.0834 0.4305 0.031 Uiso 0.4 1 calc R U P B 2
H22A H 0.3460 0.0883 0.4595 0.031 Uiso 0.6 1 calc R U P B 1
H22B H 0.3520 0.1655 0.3674 0.031 Uiso 0.6 1 calc R U P B 1
C23 C 0.37368(12) -0.00539(13) 0.11792(11) 0.0303(3) Uani 1 1 d . . . . .
H23A H 0.3320 -0.0208 0.0449 0.045 Uiso 1 1 calc R U . . .
H23B H 0.3658 0.0641 0.1309 0.045 Uiso 1 1 calc R U . . .
H23C H 0.3386 -0.0430 0.1668 0.045 Uiso 1 1 calc R U . . .
C24 C 1.05623(12) 0.37514(10) 0.54339(11) 0.0241(3) Uani 1 1 d . . . . .
H24A H 1.0523 0.3622 0.4686 0.036 Uiso 1 1 calc R U . . .
H24B H 1.1122 0.3297 0.5875 0.036 Uiso 1 1 calc R U . . .
H24C H 1.0836 0.4419 0.5606 0.036 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 N1 1.8471(11) . ?
Ni1 N8 1.8486(11) . ?
Ni1 N4 1.8845(10) . ?
Ni1 N11 1.8868(10) . ?
S1 C3 1.7717(12) . ?
S1 C23 1.8050(15) . ?
N1 C14 1.2839(16) . ?
N1 N2 1.4008(14) . ?
S2 C10 1.7754(13) . ?
S2 C24 1.8048(14) . ?
N2 C3 1.3239(17) . ?
C3 N4 1.3447(16) . ?
N4 C5 1.4703(16) . ?
C5 C15 1.5363(18) . ?
C5 C6 1.5370(17) . ?
C5 H5 1.0000 . ?
C6 C7 1.5030(17) . ?
C6 C17 1.5424(18) . ?
C6 H6 1.0000 . ?
C7 N8 1.2854(16) . ?
C7 C19 1.4971(17) . ?
N8 N9 1.3987(14) . ?
N9 C10 1.3242(17) . ?
C10 N11 1.3370(16) . ?
N11 C12 1.4702(16) . ?
C12 C13 1.5295(19) . ?
C12 C16 1.5362(18) . ?
C12 H12 1.0000 . ?
C13 C14 1.5037(18) . ?
C13 C20A 1.547(3) . ?
C13 C20B 1.607(4) . ?
C13 H13 1.0000 . ?
C14 C22 1.4934(18) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.5326(19) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.5325(18) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20A C21A 1.538(4) . ?
C20A H20A 0.9900 . ?
C20A H20B 0.9900 . ?
C20B C21B 1.526(6) . ?
C20B H20C 0.9900 . ?
C20B H20D 0.9900 . ?
C21A C22 1.589(3) . ?
C21A H21A 0.9900 . ?
C21A H21B 0.9900 . ?
C21B C22 1.415(4) . ?
C21B H21C 0.9900 . ?
C21B H21D 0.9900 . ?
C22 H22C 0.9900 . ?
C22 H22D 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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
N1 Ni1 N8 168.26(5) . . ?
N1 Ni1 N4 83.29(5) . . ?
N8 Ni1 N4 96.31(5) . . ?
N1 Ni1 N11 95.91(5) . . ?
N8 Ni1 N11 83.15(5) . . ?
N4 Ni1 N11 173.47(5) . . ?
C3 S1 C23 101.98(6) . . ?
C14 N1 N2 117.43(11) . . ?
C14 N1 Ni1 126.61(9) . . ?
N2 N1 Ni1 115.21(8) . . ?
C10 S2 C24 101.47(6) . . ?
C3 N2 N1 107.13(10) . . ?
N2 C3 N4 122.95(11) . . ?
N2 C3 S1 115.34(9) . . ?
N4 C3 S1 121.66(10) . . ?
C3 N4 C5 121.15(10) . . ?
C3 N4 Ni1 107.42(8) . . ?
C5 N4 Ni1 127.94(8) . . ?
N4 C5 C15 113.09(11) . . ?
N4 C5 C6 111.38(10) . . ?
C15 C5 C6 106.57(11) . . ?
N4 C5 H5 108.6 . . ?
C15 C5 H5 108.6 . . ?
C6 C5 H5 108.6 . . ?
C7 C6 C5 117.53(10) . . ?
C7 C6 C17 103.24(10) . . ?
C5 C6 C17 113.26(10) . . ?
C7 C6 H6 107.4 . . ?
C5 C6 H6 107.4 . . ?
C17 C6 H6 107.4 . . ?
N8 C7 C19 125.47(12) . . ?
N8 C7 C6 122.22(11) . . ?
C19 C7 C6 112.21(11) . . ?
C7 N8 N9 116.88(11) . . ?
C7 N8 Ni1 126.91(9) . . ?
N9 N8 Ni1 115.50(8) . . ?
C10 N9 N8 107.19(10) . . ?
N9 C10 N11 123.15(11) . . ?
N9 C10 S2 114.85(9) . . ?
N11 C10 S2 121.97(10) . . ?
C10 N11 C12 122.16(10) . . ?
C10 N11 Ni1 108.17(8) . . ?
C12 N11 Ni1 128.47(8) . . ?
N11 C12 C13 111.57(10) . . ?
N11 C12 C16 113.23(11) . . ?
C13 C12 C16 106.71(11) . . ?
N11 C12 H12 108.4 . . ?
C13 C12 H12 108.4 . . ?
C16 C12 H12 108.4 . . ?
C14 C13 C12 118.50(12) . . ?
C14 C13 C20A 107.17(14) . . ?
C12 C13 C20A 116.51(15) . . ?
C14 C13 C20B 96.22(19) . . ?
C12 C13 C20B 107.90(19) . . ?
C14 C13 H13 104.3 . . ?
C12 C13 H13 104.3 . . ?
C20A C13 H13 104.3 . . ?
N1 C14 C22 126.00(12) . . ?
N1 C14 C13 122.43(11) . . ?
C22 C14 C13 111.49(11) . . ?
C5 C15 H15A 109.5 . . ?
C5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C6 105.29(10) . . ?
C18 C17 H17A 110.7 . . ?
C6 C17 H17A 110.7 . . ?
C18 C17 H17B 110.7 . . ?
C6 C17 H17B 110.7 . . ?
H17A C17 H17B 108.8 . . ?
C19 C18 C17 105.42(10) . . ?
C19 C18 H18A 110.7 . . ?
C17 C18 H18A 110.7 . . ?
C19 C18 H18B 110.7 . . ?
C17 C18 H18B 110.7 . . ?
H18A C18 H18B 108.8 . . ?
C7 C19 C18 103.81(11) . . ?
C7 C19 H19A 111.0 . . ?
C18 C19 H19A 111.0 . . ?
C7 C19 H19B 111.0 . . ?
C18 C19 H19B 111.0 . . ?
H19A C19 H19B 109.0 . . ?
C21A C20A C13 102.05(19) . . ?
C21A C20A H20A 111.4 . . ?
C13 C20A H20A 111.4 . . ?
C21A C20A H20B 111.4 . . ?
C13 C20A H20B 111.4 . . ?
H20A C20A H20B 109.2 . . ?
C21B C20B C13 105.4(3) . . ?
C21B C20B H20C 110.7 . . ?
C13 C20B H20C 110.7 . . ?
C21B C20B H20D 110.7 . . ?
C13 C20B H20D 110.7 . . ?
H20C C20B H20D 108.8 . . ?
C20A C21A C22 106.7(2) . . ?
C20A C21A H21A 110.4 . . ?
C22 C21A H21A 110.4 . . ?
C20A C21A H21B 110.4 . . ?
C22 C21A H21B 110.4 . . ?
H21A C21A H21B 108.6 . . ?
C22 C21B C20B 103.0(3) . . ?
C22 C21B H21C 111.2 . . ?
C20B C21B H21C 111.2 . . ?
C22 C21B H21D 111.2 . . ?
C20B C21B H21D 111.2 . . ?
H21C C21B H21D 109.1 . . ?
C21B C22 C14 108.5(2) . . ?
C14 C22 C21A 100.33(14) . . ?
C21B C22 H22C 110.0 . . ?
C14 C22 H22C 110.0 . . ?
C21B C22 H22D 110.0 . . ?
C14 C22 H22D 110.0 . . ?
H22C C22 H22D 108.4 . . ?
C14 C22 H22A 111.7 . . ?
C21A C22 H22A 111.7 . . ?
C14 C22 H22B 111.7 . . ?
C21A C22 H22B 111.7 . . ?
H22A C22 H22B 109.5 . . ?
S1 C23 H23A 109.5 . . ?
S1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
S1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
S2 C24 H24A 109.5 . . ?
S2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
S2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

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
N8 Ni1 N1 C14 -97.2(2) . . . . ?
N4 Ni1 N1 C14 174.04(12) . . . . ?
N11 Ni1 N1 C14 -12.48(12) . . . . ?
N8 Ni1 N1 N2 72.5(2) . . . . ?
N4 Ni1 N1 N2 -16.18(8) . . . . ?
N11 Ni1 N1 N2 157.30(8) . . . . ?
C14 N1 N2 C3 -178.93(11) . . . . ?
Ni1 N1 N2 C3 10.30(12) . . . . ?
N1 N2 C3 N4 5.75(16) . . . . ?
N1 N2 C3 S1 -171.89(8) . . . . ?
C23 S1 C3 N2 -0.77(12) . . . . ?
C23 S1 C3 N4 -178.44(11) . . . . ?
N2 C3 N4 C5 -178.48(11) . . . . ?
S1 C3 N4 C5 -0.99(16) . . . . ?
N2 C3 N4 Ni1 -17.99(15) . . . . ?
S1 C3 N4 Ni1 159.51(7) . . . . ?
N1 Ni1 N4 C3 17.32(8) . . . . ?
N8 Ni1 N4 C3 -150.87(8) . . . . ?
N1 Ni1 N4 C5 176.08(11) . . . . ?
N8 Ni1 N4 C5 7.89(11) . . . . ?
C3 N4 C5 C15 -66.07(15) . . . . ?
Ni1 N4 C5 C15 137.75(10) . . . . ?
C3 N4 C5 C6 173.94(11) . . . . ?
Ni1 N4 C5 C6 17.77(15) . . . . ?
N4 C5 C6 C7 -46.10(14) . . . . ?
C15 C5 C6 C7 -169.87(11) . . . . ?
N4 C5 C6 C17 -166.44(10) . . . . ?
C15 C5 C6 C17 69.79(13) . . . . ?
C5 C6 C7 N8 47.74(16) . . . . ?
C17 C6 C7 N8 173.19(11) . . . . ?
C5 C6 C7 C19 -135.78(11) . . . . ?
C17 C6 C7 C19 -10.33(13) . . . . ?
C19 C7 N8 N9 -0.03(17) . . . . ?
C6 C7 N8 N9 175.97(10) . . . . ?
C19 C7 N8 Ni1 169.80(9) . . . . ?
C6 C7 N8 Ni1 -14.20(17) . . . . ?
N1 Ni1 N8 C7 -98.4(2) . . . . ?
N4 Ni1 N8 C7 -11.04(11) . . . . ?
N11 Ni1 N8 C7 175.51(11) . . . . ?
N1 Ni1 N8 N9 71.5(2) . . . . ?
N4 Ni1 N8 N9 158.92(8) . . . . ?
N11 Ni1 N8 N9 -14.54(8) . . . . ?
C7 N8 N9 C10 -178.42(11) . . . . ?
Ni1 N8 N9 C10 10.58(12) . . . . ?
N8 N9 C10 N11 2.55(16) . . . . ?
N8 N9 C10 S2 -175.35(8) . . . . ?
C24 S2 C10 N9 -6.76(11) . . . . ?
C24 S2 C10 N11 175.31(10) . . . . ?
N9 C10 N11 C12 177.94(11) . . . . ?
S2 C10 N11 C12 -4.30(17) . . . . ?
N9 C10 N11 Ni1 -13.58(15) . . . . ?
S2 C10 N11 Ni1 164.18(7) . . . . ?
N1 Ni1 N11 C10 -153.86(9) . . . . ?
N8 Ni1 N11 C10 14.36(8) . . . . ?
N1 Ni1 N11 C12 13.66(11) . . . . ?
N8 Ni1 N11 C12 -178.12(11) . . . . ?
C10 N11 C12 C13 176.37(12) . . . . ?
Ni1 N11 C12 C13 10.40(16) . . . . ?
C10 N11 C12 C16 -63.23(16) . . . . ?
Ni1 N11 C12 C16 130.81(11) . . . . ?
N11 C12 C13 C14 -41.69(17) . . . . ?
C16 C12 C13 C14 -165.86(12) . . . . ?
N11 C12 C13 C20A -171.95(16) . . . . ?
C16 C12 C13 C20A 63.89(19) . . . . ?
N11 C12 C13 C20B -149.4(2) . . . . ?
C16 C12 C13 C20B 86.4(2) . . . . ?
N2 N1 C14 C22 -0.49(19) . . . . ?
Ni1 N1 C14 C22 169.09(10) . . . . ?
N2 N1 C14 C13 175.93(12) . . . . ?
Ni1 N1 C14 C13 -14.49(18) . . . . ?
C12 C13 C14 N1 47.24(19) . . . . ?
C20A C13 C14 N1 -178.38(16) . . . . ?
C20B C13 C14 N1 161.5(2) . . . . ?
C12 C13 C14 C22 -135.87(13) . . . . ?
C20A C13 C14 C22 -1.50(19) . . . . ?
C20B C13 C14 C22 -21.6(2) . . . . ?
C7 C6 C17 C18 26.00(13) . . . . ?
C5 C6 C17 C18 154.17(11) . . . . ?
C6 C17 C18 C19 -32.62(13) . . . . ?
N8 C7 C19 C18 166.93(12) . . . . ?
C6 C7 C19 C18 -9.41(14) . . . . ?
C17 C18 C19 C7 25.58(13) . . . . ?
C14 C13 C20A C21A -19.9(2) . . . . ?
C12 C13 C20A C21A 115.6(2) . . . . ?
C20B C13 C20A C21A 43.4(5) . . . . ?
C14 C13 C20B C21B 35.9(3) . . . . ?
C12 C13 C20B C21B 158.6(3) . . . . ?
C20A C13 C20B C21B -84.9(6) . . . . ?
C13 C20A C21A C22 33.5(3) . . . . ?
C13 C20B C21B C22 -38.8(4) . . . . ?
C20B C21B C22 C14 24.5(3) . . . . ?
C20B C21B C22 C21A -47.7(5) . . . . ?
N1 C14 C22 C21B 176.0(2) . . . . ?
C13 C14 C22 C21B -0.8(2) . . . . ?
N1 C14 C22 C21A -161.94(16) . . . . ?
C13 C14 C22 C21A 21.31(17) . . . . ?
C20A C21A C22 C21B 79.3(6) . . . . ?
C20A C21A C22 C14 -34.0(2) . . . . ?

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
C15 H15C S1 0.98 2.51 3.1957(16) 126.5 .
C16 H16C S2 0.98 2.53 3.2133(16) 127.1 .

_refine_diff_density_max         0.478
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.061

_shelxl_version_number           2014-3



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_iube252
_database_code_depnum_ccdc_archive 'CCDC 2324336'
loop_
_audit_author_name
_audit_author_address
'Vladimir Arion'
;Institute of Inorganic Chemistry of the University of Vienna
Austria
;
_audit_update_record             
;
2024-01-09 deposited with the CCDC.	2024-08-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H32 N6 Ni S2'
_chemical_formula_sum            'C20 H32 N6 Ni S2'
_chemical_formula_weight         479.34

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'
Ni Ni 0.3393 1.1124 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.6032(10)
_cell_length_b                   13.6885(12)
_cell_length_c                   16.1127(13)
_cell_angle_alpha                112.018(3)
_cell_angle_beta                 90.826(3)
_cell_angle_gamma                107.495(3)
_cell_volume                     2239.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2569
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      24.46

_exptl_crystal_description       stick
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.072
_shelx_estimated_absorpt_T_min   0.775
_shelx_estimated_absorpt_T_max   0.948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8790
_exptl_absorpt_correction_T_max  0.9480
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            81029
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.700
_diffrn_reflns_theta_max         30.577
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             13710
_reflns_number_gt                9571
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'SAINT v8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT v8.38A (Bruker, 2018)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0307P)²+1.1020P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         13710
_refine_ls_number_parameters     531
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0869
_refine_ls_wR_factor_gt          0.0753
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.72223(2) 0.08083(2) 0.12891(2) 0.01915(6) Uani 1 1 d . . . . .
S1 S 0.74404(5) -0.24098(4) 0.10205(4) 0.03306(12) Uani 1 1 d . . . . .
S2 S 0.74224(5) 0.41533(4) 0.30239(4) 0.03930(13) Uani 1 1 d . . . . .
N1 N 0.87393(14) 0.06292(12) 0.12395(10) 0.0232(3) Uani 1 1 d . . . . .
N2 N 0.87703(14) -0.03965(12) 0.12058(11) 0.0277(3) Uani 1 1 d . . . . .
C3 C 0.76262(17) -0.10623(14) 0.10536(12) 0.0242(4) Uani 1 1 d . . . . .
N4 N 0.66730(13) -0.07426(11) 0.09372(10) 0.0218(3) Uani 1 1 d . . . . .
C5 C 0.54118(16) -0.15024(14) 0.07619(12) 0.0231(4) Uani 1 1 d . . . . .
H5 H 0.5288 -0.1803 0.1244 0.028 Uiso 1 1 calc R U . . .
C6 C 0.44730(16) -0.09158(14) 0.07664(12) 0.0227(4) Uani 1 1 d . . . . .
H6 H 0.4369 -0.0910 0.0151 0.027 Uiso 1 1 calc R U . . .
C7 C 0.47151(16) 0.02612(14) 0.14394(11) 0.0203(3) Uani 1 1 d . . . . .
N8 N 0.57593(13) 0.10195(12) 0.16064(10) 0.0205(3) Uani 1 1 d . . . . .
N9 N 0.58601(14) 0.21121(12) 0.21865(10) 0.0257(3) Uani 1 1 d . . . . .
C10 C 0.69858(17) 0.27526(14) 0.22252(12) 0.0245(4) Uani 1 1 d . . . . .
N11 N 0.77953(14) 0.23727(12) 0.17307(10) 0.0236(3) Uani 1 1 d . . . . .
C12 C 0.90368(16) 0.31249(14) 0.18056(13) 0.0251(4) Uani 1 1 d . . . . .
H12 H 0.9394 0.3523 0.2459 0.030 Uiso 1 1 calc R U . . .
C13 C 0.98628(17) 0.24801(15) 0.12963(13) 0.0263(4) Uani 1 1 d . . . . .
H13 H 0.9683 0.2332 0.0643 0.032 Uiso 1 1 calc R U . . .
C14 C 0.97685(17) 0.13818(15) 0.13408(13) 0.0259(4) Uani 1 1 d . . . . .
C15 C 0.5127(2) -0.24867(16) -0.01615(15) 0.0399(5) Uani 1 1 d . . . . .
H15A H 0.4277 -0.2966 -0.0253 0.060 Uiso 1 1 calc R U . . .
H15B H 0.5671 -0.2920 -0.0181 0.060 Uiso 1 1 calc R U . . .
H15C H 0.5253 -0.2204 -0.0640 0.060 Uiso 1 1 calc R U . . .
C16 C 0.9055(2) 0.39960(16) 0.14206(15) 0.0360(5) Uani 1 1 d . . . . .
H16A H 0.9890 0.4511 0.1526 0.054 Uiso 1 1 calc R U . . .
H16B H 0.8520 0.4414 0.1720 0.054 Uiso 1 1 calc R U . . .
H16C H 0.8765 0.3620 0.0769 0.054 Uiso 1 1 calc R U . . .
C17 C 0.32068(18) -0.15271(16) 0.09283(15) 0.0352(5) Uani 1 1 d . . . . .
H17A H 0.2756 -0.2178 0.0371 0.042 Uiso 1 1 calc R U . . .
H17B H 0.3279 -0.1787 0.1417 0.042 Uiso 1 1 calc R U . . .
C18 C 0.25655(18) -0.06512(17) 0.12011(15) 0.0376(5) Uani 1 1 d . . . . .
H18A H 0.1893 -0.0841 0.1544 0.045 Uiso 1 1 calc R U . . .
H18B H 0.2231 -0.0587 0.0662 0.045 Uiso 1 1 calc R U . . .
C19 C 0.35735(17) 0.04303(16) 0.17951(13) 0.0296(4) Uani 1 1 d . . . . .
H19A H 0.3444 0.1084 0.1733 0.036 Uiso 1 1 calc R U . . .
H19B H 0.3607 0.0540 0.2439 0.036 Uiso 1 1 calc R U . . .
C20 C 1.12313(18) 0.31437(18) 0.15953(16) 0.0386(5) Uani 1 1 d . . . . .
H20A H 1.1506 0.3659 0.1286 0.046 Uiso 1 1 calc R U . . .
H20B H 1.1401 0.3585 0.2257 0.046 Uiso 1 1 calc R U . . .
C21 C 1.18785(19) 0.22777(19) 0.13299(16) 0.0407(5) Uani 1 1 d . . . . .
H21A H 1.2655 0.2556 0.1739 0.049 Uiso 1 1 calc R U . . .
H21B H 1.2056 0.2098 0.0701 0.049 Uiso 1 1 calc R U . . .
C22 C 1.09922(17) 0.12492(17) 0.14176(15) 0.0345(5) Uani 1 1 d . . . . .
H22A H 1.1015 0.0554 0.0928 0.041 Uiso 1 1 calc R U . . .
H22B H 1.1195 0.1229 0.2009 0.041 Uiso 1 1 calc R U . . .
C23 C 0.9006(2) -0.24008(18) 0.10956(15) 0.0380(5) Uani 1 1 d . . . . .
H23A H 0.9456 -0.2045 0.0710 0.046 Uiso 1 1 calc R U . . .
H23B H 0.9417 -0.1964 0.1728 0.046 Uiso 1 1 calc R U . . .
C24 C 0.9015(3) -0.3595(2) 0.07855(17) 0.0533(7) Uani 1 1 d . . . . .
H24A H 0.9855 -0.3587 0.0881 0.080 Uiso 1 1 calc R U . . .
H24B H 0.8688 -0.4002 0.0141 0.080 Uiso 1 1 calc R U . . .
H24C H 0.8509 -0.3964 0.1135 0.080 Uiso 1 1 calc R U . . .
C25 C 0.6018(2) 0.42817(17) 0.34303(15) 0.0377(5) Uani 1 1 d . . . . .
H25A H 0.5572 0.3599 0.3523 0.045 Uiso 1 1 calc R U . . .
H25B H 0.6212 0.4920 0.4025 0.045 Uiso 1 1 calc R U . . .
C26 C 0.5201(2) 0.4451(2) 0.28061(18) 0.0560(7) Uani 1 1 d . . . . .
H26A H 0.4473 0.4549 0.3081 0.084 Uiso 1 1 calc R U . . .
H26B H 0.4955 0.3798 0.2229 0.084 Uiso 1 1 calc R U . . .
H26C H 0.5639 0.5118 0.2700 0.084 Uiso 1 1 calc R U . . .
C33 C 0.47704(16) -0.02597(14) 0.61648(12) 0.0215(3) Uani 1 1 d . . . . .
N34 N 0.58080(13) 0.05076(11) 0.63360(10) 0.0204(3) Uani 1 1 d . . . . .
N35 N 0.58590(14) 0.15990(12) 0.68793(11) 0.0254(3) Uani 1 1 d . . . . .
C36 C 0.69967(17) 0.22594(14) 0.69749(12) 0.0239(4) Uani 1 1 d . . . . .
N37 N 0.78651(13) 0.18922(11) 0.65590(10) 0.0222(3) Uani 1 1 d . . . . .
C38 C 0.91298(16) 0.26474(14) 0.67082(13) 0.0234(4) Uani 1 1 d . . . . .
H38 H 0.9426 0.3013 0.7373 0.028 Uiso 1 1 calc R U . . .
C39 C 0.99868(16) 0.20156(15) 0.62359(13) 0.0247(4) Uani 1 1 d . . . . .
H39 H 0.9851 0.1870 0.5580 0.030 Uiso 1 1 calc R U . . .
C40 C 0.98675(16) 0.09177(15) 0.62899(12) 0.0231(4) Uani 1 1 d . . . . .
C41 C 0.5262(2) -0.29739(17) 0.46090(16) 0.0460(6) Uani 1 1 d . . . . .
H41A H 0.4437 -0.3501 0.4517 0.069 Uiso 1 1 calc R U . . .
H41B H 0.5860 -0.3356 0.4583 0.069 Uiso 1 1 calc R U . . .
H41C H 0.5337 -0.2683 0.4134 0.069 Uiso 1 1 calc R U . . .
C42 C 0.92460(18) 0.35608(16) 0.63504(14) 0.0318(4) Uani 1 1 d . . . . .
H42A H 1.0088 0.4076 0.6515 0.048 Uiso 1 1 calc R U . . .
H42B H 0.8691 0.3972 0.6618 0.048 Uiso 1 1 calc R U . . .
H42C H 0.9033 0.3218 0.5691 0.048 Uiso 1 1 calc R U . . .
C43 C 0.32904(17) -0.20565(16) 0.56948(15) 0.0335(5) Uani 1 1 d . . . . .
H43A H 0.2844 -0.2721 0.5144 0.040 Uiso 1 1 calc R U . . .
H43B H 0.3378 -0.2297 0.6193 0.040 Uiso 1 1 calc R U . . .
C44 C 0.26252(18) -0.12006(16) 0.59517(15) 0.0352(5) Uani 1 1 d . . . . .
H44A H 0.1979 -0.1377 0.6318 0.042 Uiso 1 1 calc R U . . .
H44B H 0.2251 -0.1180 0.5405 0.042 Uiso 1 1 calc R U . . .
C45 C 0.36229(17) -0.00901(16) 0.65031(14) 0.0299(4) Uani 1 1 d . . . . .
H45A H 0.3472 0.0531 0.6397 0.036 Uiso 1 1 calc R U . . .
H45B H 0.3666 0.0074 0.7158 0.036 Uiso 1 1 calc R U . . .
C46 C 1.13471(17) 0.26916(17) 0.65831(15) 0.0339(5) Uani 1 1 d . . . . .
H46A H 1.1659 0.3191 0.6265 0.041 Uiso 1 1 calc R U . . .
H46B H 1.1469 0.3151 0.7240 0.041 Uiso 1 1 calc R U . . .
C47 C 1.20073(18) 0.18321(17) 0.63868(15) 0.0341(5) Uani 1 1 d . . . . .
H47A H 1.2737 0.2117 0.6844 0.041 Uiso 1 1 calc R U . . .
H47B H 1.2268 0.1659 0.5780 0.041 Uiso 1 1 calc R U . . .
C48 C 1.10801(17) 0.07918(16) 0.64294(14) 0.0294(4) Uani 1 1 d . . . . .
H48A H 1.1136 0.0105 0.5949 0.035 Uiso 1 1 calc R U . . .
H48B H 1.1220 0.0759 0.7024 0.035 Uiso 1 1 calc R U . . .
C49 C 0.9022(2) -0.29168(18) 0.59847(16) 0.0394(5) Uani 1 1 d . . . . .
H49A H 0.9493 -0.2593 0.5588 0.047 Uiso 1 1 calc R U . . .
H49B H 0.9427 -0.2465 0.6617 0.047 Uiso 1 1 calc R U . . .
Ni2 Ni 0.73052(2) 0.03229(2) 0.61106(2) 0.01903(6) Uani 1 1 d . . . . .
S3 S 0.74730(5) -0.28975(4) 0.58817(4) 0.03736(13) Uani 1 1 d . . . . .
S4 S 0.73011(5) 0.36666(4) 0.77312(4) 0.03802(13) Uani 1 1 d . . . . .
N27 N 0.88282(14) 0.01597(12) 0.61461(10) 0.0225(3) Uani 1 1 d . . . . .
N28 N 0.88418(14) -0.08737(12) 0.61164(11) 0.0268(3) Uani 1 1 d . . . . .
C29 C 0.76916(17) -0.15429(14) 0.59195(12) 0.0240(4) Uani 1 1 d . . . . .
N30 N 0.67538(14) -0.12303(11) 0.57577(10) 0.0221(3) Uani 1 1 d . . . . .
C31 C 0.54981(17) -0.20063(14) 0.55350(13) 0.0255(4) Uani 1 1 d . . . . .
H31 H 0.5348 -0.2326 0.6005 0.031 Uiso 1 1 calc R U . . .
C32 C 0.45428(16) -0.14422(14) 0.55210(12) 0.0234(4) Uani 1 1 d . . . . .
H32 H 0.4428 -0.1465 0.4897 0.028 Uiso 1 1 calc R U . . .
C50 C 0.8980(3) -0.4118(2) 0.57106(17) 0.0547(7) Uani 1 1 d . . . . .
H50A H 0.9805 -0.4134 0.5824 0.082 Uiso 1 1 calc R U . . .
H50B H 0.8662 -0.4540 0.5066 0.082 Uiso 1 1 calc R U . . .
H50C H 0.8446 -0.4455 0.6066 0.082 Uiso 1 1 calc R U . . .
C51 C 0.58277(19) 0.36476(16) 0.80893(15) 0.0359(5) Uani 1 1 d . . . . .
H51A H 0.5261 0.3571 0.7586 0.043 Uiso 1 1 calc R U . . .
H51B H 0.5483 0.2998 0.8251 0.043 Uiso 1 1 calc R U . . .
C52 C 0.5953(2) 0.4706(2) 0.88928(18) 0.0560(7) Uani 1 1 d . . . . .
H52A H 0.5146 0.4697 0.9070 0.084 Uiso 1 1 calc R U . . .
H52B H 0.6307 0.5349 0.8735 0.084 Uiso 1 1 calc R U . . .
H52C H 0.6487 0.4764 0.9398 0.084 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 N1 1.8476(15) . ?
Ni1 N8 1.8535(15) . ?
Ni1 N4 1.8729(14) . ?
Ni1 N11 1.8767(14) . ?
S1 C3 1.7717(18) . ?
S1 C23 1.815(2) . ?
S2 C10 1.7709(18) . ?
S2 C25 1.798(2) . ?
N1 C14 1.282(2) . ?
N1 N2 1.396(2) . ?
N2 C3 1.322(2) . ?
C3 N4 1.340(2) . ?
N4 C5 1.468(2) . ?
C5 C6 1.534(2) . ?
C5 C15 1.534(3) . ?
C5 H5 1.0000 . ?
C6 C7 1.503(2) . ?
C6 C17 1.537(3) . ?
C6 H6 1.0000 . ?
C7 N8 1.282(2) . ?
C7 C19 1.498(2) . ?
N8 N9 1.4028(19) . ?
N9 C10 1.322(2) . ?
C10 N11 1.339(2) . ?
N11 C12 1.470(2) . ?
C12 C16 1.532(3) . ?
C12 C13 1.536(3) . ?
C12 H12 1.0000 . ?
C13 C14 1.503(3) . ?
C13 C20 1.537(3) . ?
C13 H13 1.0000 . ?
C14 C22 1.494(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.528(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.530(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.522(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.531(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.523(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.498(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C33 N34 1.281(2) . ?
C33 C45 1.495(2) . ?
C33 C32 1.497(2) . ?
N34 N35 1.4023(19) . ?
N34 Ni2 1.8513(14) . ?
N35 C36 1.325(2) . ?
C36 N37 1.337(2) . ?
C36 S4 1.7716(18) . ?
N37 C38 1.474(2) . ?
N37 Ni2 1.8820(14) . ?
C38 C42 1.535(2) . ?
C38 C39 1.537(2) . ?
C38 H38 1.0000 . ?
C39 C40 1.503(2) . ?
C39 C46 1.539(3) . ?
C39 H39 1.0000 . ?
C40 N27 1.282(2) . ?
C40 C48 1.492(2) . ?
C41 C31 1.531(3) . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 C44 1.526(3) . ?
C43 C32 1.533(3) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 C45 1.530(3) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C46 C47 1.530(3) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C47 C48 1.531(3) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C49 C50 1.519(3) . ?
C49 S3 1.811(2) . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
Ni2 N27 1.8493(15) . ?
Ni2 N30 1.8757(14) . ?
S3 C29 1.7716(18) . ?
S4 C51 1.808(2) . ?
N27 N28 1.4022(19) . ?
N28 C29 1.325(2) . ?
C29 N30 1.338(2) . ?
N30 C31 1.466(2) . ?
C31 C32 1.534(2) . ?
C31 H31 1.0000 . ?
C32 H32 1.0000 . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 0.9800 . ?
C51 C52 1.503(3) . ?
C51 H51A 0.9900 . ?
C51 H51B 0.9900 . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?

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
N1 Ni1 N8 167.02(6) . . ?
N1 Ni1 N4 83.06(6) . . ?
N8 Ni1 N4 96.46(6) . . ?
N1 Ni1 N11 96.35(6) . . ?
N8 Ni1 N11 83.16(6) . . ?
N4 Ni1 N11 175.73(7) . . ?
C3 S1 C23 102.08(10) . . ?
C10 S2 C25 103.38(9) . . ?
C14 N1 N2 116.98(15) . . ?
C14 N1 Ni1 126.92(13) . . ?
N2 N1 Ni1 115.54(11) . . ?
C3 N2 N1 107.20(14) . . ?
N2 C3 N4 122.63(16) . . ?
N2 C3 S1 115.14(13) . . ?
N4 C3 S1 122.22(14) . . ?
C3 N4 C5 121.49(14) . . ?
C3 N4 Ni1 108.75(12) . . ?
C5 N4 Ni1 128.37(11) . . ?
N4 C5 C6 112.26(14) . . ?
N4 C5 C15 112.26(15) . . ?
C6 C5 C15 106.46(15) . . ?
N4 C5 H5 108.6 . . ?
C6 C5 H5 108.6 . . ?
C15 C5 H5 108.6 . . ?
C7 C6 C5 119.67(15) . . ?
C7 C6 C17 102.27(15) . . ?
C5 C6 C17 113.47(15) . . ?
C7 C6 H6 106.9 . . ?
C5 C6 H6 106.9 . . ?
C17 C6 H6 106.9 . . ?
N8 C7 C19 126.15(16) . . ?
N8 C7 C6 122.16(15) . . ?
C19 C7 C6 111.43(15) . . ?
C7 N8 N9 117.60(14) . . ?
C7 N8 Ni1 126.86(12) . . ?
N9 N8 Ni1 115.00(11) . . ?
C10 N9 N8 107.07(14) . . ?
N9 C10 N11 123.09(16) . . ?
N9 C10 S2 116.49(14) . . ?
N11 C10 S2 120.32(13) . . ?
C10 N11 C12 120.61(15) . . ?
C10 N11 Ni1 108.10(11) . . ?
C12 N11 Ni1 128.79(12) . . ?
N11 C12 C16 112.41(15) . . ?
N11 C12 C13 111.59(14) . . ?
C16 C12 C13 107.07(16) . . ?
N11 C12 H12 108.6 . . ?
C16 C12 H12 108.6 . . ?
C13 C12 H12 108.6 . . ?
C14 C13 C12 119.20(15) . . ?
C14 C13 C20 102.78(16) . . ?
C12 C13 C20 113.35(16) . . ?
C14 C13 H13 106.9 . . ?
C12 C13 H13 106.9 . . ?
C20 C13 H13 106.9 . . ?
N1 C14 C22 125.52(17) . . ?
N1 C14 C13 122.34(17) . . ?
C22 C14 C13 111.85(16) . . ?
C5 C15 H15A 109.5 . . ?
C5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C6 104.29(16) . . ?
C18 C17 H17A 110.9 . . ?
C6 C17 H17A 110.9 . . ?
C18 C17 H17B 110.9 . . ?
C6 C17 H17B 110.9 . . ?
H17A C17 H17B 108.9 . . ?
C17 C18 C19 103.95(16) . . ?
C17 C18 H18A 111.0 . . ?
C19 C18 H18A 111.0 . . ?
C17 C18 H18B 111.0 . . ?
C19 C18 H18B 111.0 . . ?
H18A C18 H18B 109.0 . . ?
C7 C19 C18 103.70(15) . . ?
C7 C19 H19A 111.0 . . ?
C18 C19 H19A 111.0 . . ?
C7 C19 H19B 111.0 . . ?
C18 C19 H19B 111.0 . . ?
H19A C19 H19B 109.0 . . ?
C21 C20 C13 105.75(17) . . ?
C21 C20 H20A 110.6 . . ?
C13 C20 H20A 110.6 . . ?
C21 C20 H20B 110.6 . . ?
C13 C20 H20B 110.6 . . ?
H20A C20 H20B 108.7 . . ?
C20 C21 C22 105.35(17) . . ?
C20 C21 H21A 110.7 . . ?
C22 C21 H21A 110.7 . . ?
C20 C21 H21B 110.7 . . ?
C22 C21 H21B 110.7 . . ?
H21A C21 H21B 108.8 . . ?
C14 C22 C21 104.40(17) . . ?
C14 C22 H22A 110.9 . . ?
C21 C22 H22A 110.9 . . ?
C14 C22 H22B 110.9 . . ?
C21 C22 H22B 110.9 . . ?
H22A C22 H22B 108.9 . . ?
C24 C23 S1 109.46(17) . . ?
C24 C23 H23A 109.8 . . ?
S1 C23 H23A 109.8 . . ?
C24 C23 H23B 109.8 . . ?
S1 C23 H23B 109.8 . . ?
H23A C23 H23B 108.2 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 S2 113.78(17) . . ?
C26 C25 H25A 108.8 . . ?
S2 C25 H25A 108.8 . . ?
C26 C25 H25B 108.8 . . ?
S2 C25 H25B 108.8 . . ?
H25A C25 H25B 107.7 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N34 C33 C45 125.60(16) . . ?
N34 C33 C32 122.83(16) . . ?
C45 C33 C32 111.37(15) . . ?
C33 N34 N35 116.72(14) . . ?
C33 N34 Ni2 127.30(12) . . ?
N35 N34 Ni2 115.16(11) . . ?
C36 N35 N34 107.37(14) . . ?
N35 C36 N37 122.98(16) . . ?
N35 C36 S4 114.85(13) . . ?
N37 C36 S4 122.13(14) . . ?
C36 N37 C38 121.24(14) . . ?
C36 N37 Ni2 108.30(11) . . ?
C38 N37 Ni2 127.99(11) . . ?
N37 C38 C42 112.93(15) . . ?
N37 C38 C39 111.78(14) . . ?
C42 C38 C39 106.45(15) . . ?
N37 C38 H38 108.5 . . ?
C42 C38 H38 108.5 . . ?
C39 C38 H38 108.5 . . ?
C40 C39 C38 118.61(15) . . ?
C40 C39 C46 103.11(15) . . ?
C38 C39 C46 113.20(15) . . ?
C40 C39 H39 107.1 . . ?
C38 C39 H39 107.1 . . ?
C46 C39 H39 107.1 . . ?
N27 C40 C48 125.56(17) . . ?
N27 C40 C39 122.05(16) . . ?
C48 C40 C39 112.09(16) . . ?
C31 C41 H41A 109.5 . . ?
C31 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C31 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C38 C42 H42A 109.5 . . ?
C38 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C38 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C44 C43 C32 104.57(15) . . ?
C44 C43 H43A 110.8 . . ?
C32 C43 H43A 110.8 . . ?
C44 C43 H43B 110.8 . . ?
C32 C43 H43B 110.8 . . ?
H43A C43 H43B 108.9 . . ?
C43 C44 C45 104.31(15) . . ?
C43 C44 H44A 110.9 . . ?
C45 C44 H44A 110.9 . . ?
C43 C44 H44B 110.9 . . ?
C45 C44 H44B 110.9 . . ?
H44A C44 H44B 108.9 . . ?
C33 C45 C44 104.08(15) . . ?
C33 C45 H45A 110.9 . . ?
C44 C45 H45A 110.9 . . ?
C33 C45 H45B 110.9 . . ?
C44 C45 H45B 110.9 . . ?
H45A C45 H45B 109.0 . . ?
C47 C46 C39 105.92(16) . . ?
C47 C46 H46A 110.6 . . ?
C39 C46 H46A 110.6 . . ?
C47 C46 H46B 110.6 . . ?
C39 C46 H46B 110.6 . . ?
H46A C46 H46B 108.7 . . ?
C46 C47 C48 105.66(16) . . ?
C46 C47 H47A 110.6 . . ?
C48 C47 H47A 110.6 . . ?
C46 C47 H47B 110.6 . . ?
C48 C47 H47B 110.6 . . ?
H47A C47 H47B 108.7 . . ?
C40 C48 C47 104.71(16) . . ?
C40 C48 H48A 110.8 . . ?
C47 C48 H48A 110.8 . . ?
C40 C48 H48B 110.8 . . ?
C47 C48 H48B 110.8 . . ?
H48A C48 H48B 108.9 . . ?
C50 C49 S3 108.67(18) . . ?
C50 C49 H49A 110.0 . . ?
S3 C49 H49A 110.0 . . ?
C50 C49 H49B 110.0 . . ?
S3 C49 H49B 110.0 . . ?
H49A C49 H49B 108.3 . . ?
N27 Ni2 N34 167.27(6) . . ?
N27 Ni2 N30 83.19(6) . . ?
N34 Ni2 N30 95.98(6) . . ?
N27 Ni2 N37 96.48(6) . . ?
N34 Ni2 N37 83.36(6) . . ?
N30 Ni2 N37 175.52(7) . . ?
C29 S3 C49 102.60(10) . . ?
C36 S4 C51 101.97(9) . . ?
C40 N27 N28 116.76(15) . . ?
C40 N27 Ni2 127.17(12) . . ?
N28 N27 Ni2 115.62(11) . . ?
C29 N28 N27 106.93(14) . . ?
N28 C29 N30 123.03(16) . . ?
N28 C29 S3 115.18(13) . . ?
N30 C29 S3 121.79(14) . . ?
C29 N30 C31 120.90(14) . . ?
C29 N30 Ni2 108.74(12) . . ?
C31 N30 Ni2 129.03(11) . . ?
N30 C31 C41 112.79(16) . . ?
N30 C31 C32 112.93(14) . . ?
C41 C31 C32 106.47(16) . . ?
N30 C31 H31 108.2 . . ?
C41 C31 H31 108.2 . . ?
C32 C31 H31 108.2 . . ?
C33 C32 C43 102.65(15) . . ?
C33 C32 C31 119.82(15) . . ?
C43 C32 C31 113.25(15) . . ?
C33 C32 H32 106.8 . . ?
C43 C32 H32 106.8 . . ?
C31 C32 H32 106.8 . . ?
C49 C50 H50A 109.5 . . ?
C49 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C49 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C52 C51 S4 110.16(16) . . ?
C52 C51 H51A 109.6 . . ?
S4 C51 H51A 109.6 . . ?
C52 C51 H51B 109.6 . . ?
S4 C51 H51B 109.6 . . ?
H51A C51 H51B 108.1 . . ?
C51 C52 H52A 109.5 . . ?
C51 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C51 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?

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
N8 Ni1 N1 C14 -97.2(3) . . . . ?
N4 Ni1 N1 C14 174.17(17) . . . . ?
N11 Ni1 N1 C14 -10.09(17) . . . . ?
N8 Ni1 N1 N2 73.9(3) . . . . ?
N4 Ni1 N1 N2 -14.79(12) . . . . ?
N11 Ni1 N1 N2 160.95(12) . . . . ?
C14 N1 N2 C3 -176.86(16) . . . . ?
Ni1 N1 N2 C3 11.17(18) . . . . ?
N1 N2 C3 N4 1.6(2) . . . . ?
N1 N2 C3 S1 -178.02(12) . . . . ?
C23 S1 C3 N2 -6.16(17) . . . . ?
C23 S1 C3 N4 174.19(16) . . . . ?
N2 C3 N4 C5 179.50(16) . . . . ?
S1 C3 N4 C5 -0.9(2) . . . . ?
N2 C3 N4 Ni1 -12.9(2) . . . . ?
S1 C3 N4 Ni1 166.71(10) . . . . ?
N1 Ni1 N4 C3 14.21(12) . . . . ?
N8 Ni1 N4 C3 -152.73(12) . . . . ?
N1 Ni1 N4 C5 -179.32(15) . . . . ?
N8 Ni1 N4 C5 13.75(15) . . . . ?
C3 N4 C5 C6 173.05(16) . . . . ?
Ni1 N4 C5 C6 8.1(2) . . . . ?
C3 N4 C5 C15 -67.1(2) . . . . ?
Ni1 N4 C5 C15 127.99(15) . . . . ?
N4 C5 C6 C7 -38.3(2) . . . . ?
C15 C5 C6 C7 -161.50(16) . . . . ?
N4 C5 C6 C17 -159.23(15) . . . . ?
C15 C5 C6 C17 77.6(2) . . . . ?
C5 C6 C7 N8 44.3(2) . . . . ?
C17 C6 C7 N8 170.70(17) . . . . ?
C5 C6 C7 C19 -141.23(17) . . . . ?
C17 C6 C7 C19 -14.9(2) . . . . ?
C19 C7 N8 N9 1.0(3) . . . . ?
C6 C7 N8 N9 174.58(15) . . . . ?
C19 C7 N8 Ni1 172.08(14) . . . . ?
C6 C7 N8 Ni1 -14.3(2) . . . . ?
N1 Ni1 N8 C7 -98.5(3) . . . . ?
N4 Ni1 N8 C7 -11.38(16) . . . . ?
N11 Ni1 N8 C7 172.90(16) . . . . ?
N1 Ni1 N8 N9 72.8(3) . . . . ?
N4 Ni1 N8 N9 159.91(12) . . . . ?
N11 Ni1 N8 N9 -15.81(12) . . . . ?
C7 N8 N9 C10 -177.05(16) . . . . ?
Ni1 N8 N9 C10 10.80(18) . . . . ?
N8 N9 C10 N11 4.1(2) . . . . ?
N8 N9 C10 S2 -172.43(12) . . . . ?
C25 S2 C10 N9 -8.03(17) . . . . ?
C25 S2 C10 N11 175.36(16) . . . . ?
N9 C10 N11 C12 -179.75(17) . . . . ?
S2 C10 N11 C12 -3.4(2) . . . . ?
N9 C10 N11 Ni1 -16.2(2) . . . . ?
S2 C10 N11 Ni1 160.19(10) . . . . ?
N1 Ni1 N11 C10 -150.63(13) . . . . ?
N8 Ni1 N11 C10 16.30(12) . . . . ?
N1 Ni1 N11 C12 11.17(16) . . . . ?
N8 Ni1 N11 C12 178.10(16) . . . . ?
C10 N11 C12 C16 -68.7(2) . . . . ?
Ni1 N11 C12 C16 131.52(15) . . . . ?
C10 N11 C12 C13 171.03(16) . . . . ?
Ni1 N11 C12 C13 11.2(2) . . . . ?
N11 C12 C13 C14 -40.2(2) . . . . ?
C16 C12 C13 C14 -163.61(16) . . . . ?
N11 C12 C13 C20 -161.36(16) . . . . ?
C16 C12 C13 C20 75.2(2) . . . . ?
N2 N1 C14 C22 0.5(3) . . . . ?
Ni1 N1 C14 C22 171.48(15) . . . . ?
N2 N1 C14 C13 173.84(16) . . . . ?
Ni1 N1 C14 C13 -15.2(3) . . . . ?
C12 C13 C14 N1 45.5(3) . . . . ?
C20 C13 C14 N1 171.79(18) . . . . ?
C12 C13 C14 C22 -140.40(18) . . . . ?
C20 C13 C14 C22 -14.1(2) . . . . ?
C7 C6 C17 C18 32.4(2) . . . . ?
C5 C6 C17 C18 162.73(16) . . . . ?
C6 C17 C18 C19 -38.6(2) . . . . ?
N8 C7 C19 C18 165.67(18) . . . . ?
C6 C7 C19 C18 -8.5(2) . . . . ?
C17 C18 C19 C7 28.7(2) . . . . ?
C14 C13 C20 C21 28.0(2) . . . . ?
C12 C13 C20 C21 157.97(17) . . . . ?
C13 C20 C21 C22 -32.1(2) . . . . ?
N1 C14 C22 C21 168.70(19) . . . . ?
C13 C14 C22 C21 -5.2(2) . . . . ?
C20 C21 C22 C14 22.7(2) . . . . ?
C3 S1 C23 C24 -162.41(16) . . . . ?
C10 S2 C25 C26 -79.51(17) . . . . ?
C45 C33 N34 N35 -0.8(3) . . . . ?
C32 C33 N34 N35 173.64(15) . . . . ?
C45 C33 N34 Ni2 168.28(14) . . . . ?
C32 C33 N34 Ni2 -17.3(3) . . . . ?
C33 N34 N35 C36 -179.98(16) . . . . ?
Ni2 N34 N35 C36 9.63(18) . . . . ?
N34 N35 C36 N37 3.6(2) . . . . ?
N34 N35 C36 S4 -174.23(12) . . . . ?
N35 C36 N37 C38 -177.89(16) . . . . ?
S4 C36 N37 C38 -0.2(2) . . . . ?
N35 C36 N37 Ni2 -14.4(2) . . . . ?
S4 C36 N37 Ni2 163.34(10) . . . . ?
C36 N37 C38 C42 -65.7(2) . . . . ?
Ni2 N37 C38 C42 134.24(14) . . . . ?
C36 N37 C38 C39 174.26(16) . . . . ?
Ni2 N37 C38 C39 14.2(2) . . . . ?
N37 C38 C39 C40 -42.9(2) . . . . ?
C42 C38 C39 C40 -166.61(16) . . . . ?
N37 C38 C39 C46 -163.87(16) . . . . ?
C42 C38 C39 C46 72.4(2) . . . . ?
C38 C39 C40 N27 46.4(2) . . . . ?
C46 C39 C40 N27 172.44(17) . . . . ?
C38 C39 C40 C48 -139.48(17) . . . . ?
C46 C39 C40 C48 -13.5(2) . . . . ?
C32 C43 C44 C45 -36.6(2) . . . . ?
N34 C33 C45 C44 168.57(18) . . . . ?
C32 C33 C45 C44 -6.4(2) . . . . ?
C43 C44 C45 C33 26.2(2) . . . . ?
C40 C39 C46 C47 26.1(2) . . . . ?
C38 C39 C46 C47 155.54(16) . . . . ?
C39 C46 C47 C48 -29.7(2) . . . . ?
N27 C40 C48 C47 169.35(18) . . . . ?
C39 C40 C48 C47 -4.5(2) . . . . ?
C46 C47 C48 C40 20.9(2) . . . . ?
C33 N34 Ni2 N27 -93.3(3) . . . . ?
N35 N34 Ni2 N27 75.9(3) . . . . ?
C33 N34 Ni2 N30 -7.70(16) . . . . ?
N35 N34 Ni2 N30 161.50(12) . . . . ?
C33 N34 Ni2 N37 176.76(16) . . . . ?
N35 N34 Ni2 N37 -14.04(12) . . . . ?
C36 N37 Ni2 N27 -152.67(12) . . . . ?
C38 N37 Ni2 N27 9.43(15) . . . . ?
C36 N37 Ni2 N34 14.52(12) . . . . ?
C38 N37 Ni2 N34 176.61(15) . . . . ?
C50 C49 S3 C29 -164.82(16) . . . . ?
N35 C36 S4 C51 -0.71(17) . . . . ?
N37 C36 S4 C51 -178.57(16) . . . . ?
C48 C40 N27 N28 -0.2(3) . . . . ?
C39 C40 N27 N28 173.10(16) . . . . ?
C48 C40 N27 Ni2 171.77(14) . . . . ?
C39 C40 N27 Ni2 -15.0(3) . . . . ?
N34 Ni2 N27 C40 -98.7(3) . . . . ?
N30 Ni2 N27 C40 174.28(16) . . . . ?
N37 Ni2 N27 C40 -10.22(17) . . . . ?
N34 Ni2 N27 N28 73.3(3) . . . . ?
N30 Ni2 N27 N28 -13.70(12) . . . . ?
N37 Ni2 N27 N28 161.80(12) . . . . ?
C40 N27 N28 C29 -177.06(16) . . . . ?
Ni2 N27 N28 C29 10.05(18) . . . . ?
N27 N28 C29 N30 2.1(2) . . . . ?
N27 N28 C29 S3 -177.98(12) . . . . ?
C49 S3 C29 N28 -7.83(17) . . . . ?
C49 S3 C29 N30 172.07(16) . . . . ?
N28 C29 N30 C31 179.47(17) . . . . ?
S3 C29 N30 C31 -0.4(2) . . . . ?
N28 C29 N30 Ni2 -12.6(2) . . . . ?
S3 C29 N30 Ni2 167.54(10) . . . . ?
N27 Ni2 N30 C29 13.44(12) . . . . ?
N34 Ni2 N30 C29 -153.77(12) . . . . ?
N27 Ni2 N30 C31 -179.89(16) . . . . ?
N34 Ni2 N30 C31 12.90(16) . . . . ?
C29 N30 C31 C41 -68.3(2) . . . . ?
Ni2 N30 C31 C41 126.44(16) . . . . ?
C29 N30 C31 C32 170.93(16) . . . . ?
Ni2 N30 C31 C32 5.7(2) . . . . ?
N34 C33 C32 C43 169.08(17) . . . . ?
C45 C33 C32 C43 -15.8(2) . . . . ?
N34 C33 C32 C31 42.6(3) . . . . ?
C45 C33 C32 C31 -142.31(17) . . . . ?
C44 C43 C32 C33 31.8(2) . . . . ?
C44 C43 C32 C31 162.44(16) . . . . ?
N30 C31 C32 C33 -34.0(2) . . . . ?
C41 C31 C32 C33 -158.29(17) . . . . ?
N30 C31 C32 C43 -155.38(16) . . . . ?
C41 C31 C32 C43 80.3(2) . . . . ?
C36 S4 C51 C52 167.40(17) . . . . ?

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
C15 H15B S1 0.98 2.54 3.221(2) 126.3 .
C16 H16B S2 0.98 2.56 3.206(2) 123.8 .
C41 H41B S3 0.98 2.54 3.213(2) 125.5 .
C42 H42A S2 0.98 3.02 4.000(2) 173.6 2_766
C42 H42B S4 0.98 2.50 3.188(2) 127.3 .

_refine_diff_density_max         0.396
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.064

_shelxl_version_number           2014-3



