# 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_1
_audit_block_doi                 10.5517/ccdc.csd.cc27q1xy
_database_code_depnum_ccdc_archive 'CCDC 2076780'
loop_
_audit_author_name
_audit_author_address
'yin qian'
;nanjing tech university
China
;
_audit_update_record             
;
2024-10-08 deposited with the CCDC.	2024-10-21 downloaded from the CCDC.
;
_audit_creation_date             2024-10-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C8 N4 Ni S4, C9 H17 N2'
_chemical_formula_sum            'C17 H17 N6 Ni S4'
_chemical_formula_weight         492.32
_chemical_melting_point          ?
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'
Ni Ni 0.3393 1.1124 '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 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.1823(4)
_cell_length_b                   20.7871(14)
_cell_length_c                   15.2194(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.373(2)
_cell_angle_gamma                90.00
_cell_volume                     2258.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4075
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      23.78
_cell_measurement_theta_min      2.38
_exptl_absorpt_coefficient_mu    1.244
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6650
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0868 before and 0.0561 after correction.
The Ratio of minimum to maximum transmission is 0.8919.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1012
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0744
_diffrn_reflns_av_unetI/netI     0.0972
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22468
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         2.38
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2381
_reflns_number_total             5184
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         5184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1709
_refine_ls_R_factor_gt           0.0582
_refine_ls_restrained_S_all      0.988
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0434P)²+0.5430P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1229
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9), C11(H11)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.75374(6) 0.50500(2) 0.42809(3) 0.05627(18) Uani 1 1 d . . .
S4 S 0.75280(13) 0.50365(5) 0.56885(6) 0.0625(3) Uani 1 1 d . . .
S1 S 0.77249(13) 0.60798(5) 0.43540(7) 0.0650(3) Uani 1 1 d . . .
S3 S 0.71882(14) 0.40281(5) 0.41875(6) 0.0677(3) Uani 1 1 d . . .
S2 S 0.76265(15) 0.50458(5) 0.28765(7) 0.0717(3) Uani 1 1 d . . .
N5 N 0.7313(6) 0.31465(19) 0.9797(3) 0.0860(11) Uani 1 1 d . . .
N6 N 0.6993(7) 0.2513(2) 0.8684(3) 0.0903(11) Uani 1 1 d . . .
N2 N 0.8039(5) 0.6147(2) 0.1006(3) 0.1024(13) Uani 1 1 d . . .
C2 C 0.7813(5) 0.58420(19) 0.2630(3) 0.0647(10) Uani 1 1 d . . .
C8 C 0.7173(5) 0.4046(2) 0.6814(3) 0.0665(11) Uani 1 1 d . . .
N3 N 0.6613(5) 0.25970(18) 0.5561(3) 0.0965(12) Uani 1 1 d . . .
C6 C 0.7251(4) 0.42412(19) 0.5917(3) 0.0562(9) Uani 1 1 d . . .
C1 C 0.7850(5) 0.62988(19) 0.3274(3) 0.0638(10) Uani 1 1 d . . .
C4 C 0.7925(6) 0.6013(2) 0.1725(3) 0.0773(12) Uani 1 1 d . . .
N4 N 0.7129(5) 0.3873(2) 0.7523(3) 0.1022(13) Uani 1 1 d . . .
C7 C 0.6827(5) 0.3131(2) 0.5430(3) 0.0699(11) Uani 1 1 d . . .
C5 C 0.7097(4) 0.37996(18) 0.5254(3) 0.0589(10) Uani 1 1 d . . .
C3 C 0.7964(6) 0.6968(2) 0.3075(3) 0.0773(12) Uani 1 1 d . . .
N1 N 0.8068(6) 0.7498(2) 0.2906(3) 0.1132(14) Uani 1 1 d . . .
C10 C 0.5351(7) 0.2512(3) 0.9049(4) 0.1005(16) Uani 1 1 d . . .
H10 H 0.4280 0.2279 0.8852 0.121 Uiso 1 1 calc R . .
C9 C 0.8142(7) 0.2896(3) 0.9144(4) 0.0952(15) Uani 1 1 d . . .
H9 H 0.9365 0.2981 0.9032 0.114 Uiso 1 1 calc R . .
C11 C 0.5562(8) 0.2908(3) 0.9739(4) 0.1053(16) Uani 1 1 d . . .
H11 H 0.4662 0.3002 1.0114 0.126 Uiso 1 1 calc R . .
C15 C 0.8187(8) 0.3602(3) 1.0459(4) 0.1217(18) Uani 1 1 d . . .
H15A H 0.9505 0.3640 1.0382 0.146 Uiso 1 1 calc R . .
H15B H 0.8104 0.3425 1.1042 0.146 Uiso 1 1 calc R . .
C17 C 0.7324(9) 0.4588(3) 0.9618(5) 0.164(3) Uani 1 1 d . . .
H17A H 0.8560 0.4585 0.9433 0.246 Uiso 1 1 calc R . .
H17B H 0.6932 0.5024 0.9691 0.246 Uiso 1 1 calc R . .
H17C H 0.6469 0.4380 0.9178 0.246 Uiso 1 1 calc R . .
C16 C 0.7343(10) 0.4260(3) 1.0420(4) 0.164(3) Uani 1 1 d . . .
H16A H 0.6062 0.4225 1.0561 0.197 Uiso 1 1 calc R . .
H16B H 0.8023 0.4520 1.0879 0.197 Uiso 1 1 calc R . .
C14 C 0.7787(8) 0.1122(3) 0.7150(4) 0.141(2) Uani 1 1 d . . .
H14A H 0.7576 0.1376 0.6622 0.211 Uiso 1 1 calc R . .
H14B H 0.7065 0.0733 0.7077 0.211 Uiso 1 1 calc R . .
H14C H 0.9093 0.1016 0.7260 0.211 Uiso 1 1 calc R . .
C12 C 0.7372(9) 0.2152(3) 0.7892(4) 0.1300(19) Uani 1 1 d . . .
H12A H 0.6528 0.2309 0.7397 0.156 Uiso 1 1 calc R . .
H12B H 0.8636 0.2253 0.7771 0.156 Uiso 1 1 calc R . .
C13 C 0.7204(9) 0.1497(3) 0.7917(4) 0.147(2) Uani 1 1 d . . .
H13A H 0.5904 0.1395 0.7972 0.176 Uiso 1 1 calc R . .
H13B H 0.7938 0.1344 0.8450 0.176 Uiso 1 1 calc R . .


_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 S4 2.1432(11) . ?
Ni1 S1 2.1471(11) . ?
Ni1 S3 2.1418(11) . ?
Ni1 S2 2.1455(11) . ?
S4 C6 1.705(4) . ?
S1 C1 1.717(4) . ?
S3 C5 1.700(4) . ?
S2 C2 1.706(4) . ?
N5 C9 1.321(6) . ?
N5 C11 1.345(5) . ?
N5 C15 1.472(6) . ?
N6 C10 1.358(6) . ?
N6 C9 1.295(5) . ?
N6 C12 1.471(6) . ?
N2 C4 1.141(5) . ?
C2 C1 1.363(5) . ?
C2 C4 1.433(6) . ?
C8 C6 1.431(5) . ?
C8 N4 1.141(5) . ?
N3 C7 1.142(5) . ?
C6 C5 1.359(5) . ?
C1 C3 1.428(5) . ?
C7 C5 1.432(5) . ?
C3 N1 1.137(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.329(6) . ?
C9 H9 0.9300 . ?
C11 H11 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.495(7) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C17 C16 1.397(7) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C14 C13 1.502(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.368(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?

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
S4 Ni1 S1 88.19(4) . . ?
S4 Ni1 S2 178.19(4) . . ?
S3 Ni1 S4 92.29(4) . . ?
S3 Ni1 S1 176.85(4) . . ?
S3 Ni1 S2 86.91(4) . . ?
S2 Ni1 S1 92.70(4) . . ?
C6 S4 Ni1 103.30(14) . . ?
C1 S1 Ni1 102.97(14) . . ?
C5 S3 Ni1 103.32(14) . . ?
C2 S2 Ni1 103.13(15) . . ?
C9 N5 C11 107.5(5) . . ?
C9 N5 C15 125.1(5) . . ?
C11 N5 C15 127.4(5) . . ?
C10 N6 C12 125.6(5) . . ?
C9 N6 C10 108.1(5) . . ?
C9 N6 C12 126.3(5) . . ?
C1 C2 S2 120.9(3) . . ?
C1 C2 C4 121.4(4) . . ?
C4 C2 S2 117.8(3) . . ?
N4 C8 C6 178.1(5) . . ?
C8 C6 S4 119.2(3) . . ?
C5 C6 S4 120.3(3) . . ?
C5 C6 C8 120.5(4) . . ?
C2 C1 S1 120.3(3) . . ?
C2 C1 C3 121.5(4) . . ?
C3 C1 S1 118.2(3) . . ?
N2 C4 C2 179.1(5) . . ?
N3 C7 C5 179.2(5) . . ?
C6 C5 S3 120.8(3) . . ?
C6 C5 C7 121.2(4) . . ?
C7 C5 S3 118.0(3) . . ?
N1 C3 C1 179.0(5) . . ?
N6 C10 H10 126.5 . . ?
C11 C10 N6 107.1(5) . . ?
C11 C10 H10 126.5 . . ?
N5 C9 H9 125.2 . . ?
N6 C9 N5 109.6(5) . . ?
N6 C9 H9 125.2 . . ?
N5 C11 H11 126.1 . . ?
C10 C11 N5 107.7(5) . . ?
C10 C11 H11 126.1 . . ?
N5 C15 H15A 108.5 . . ?
N5 C15 H15B 108.5 . . ?
N5 C15 C16 115.0(5) . . ?
H15A C15 H15B 107.5 . . ?
C16 C15 H15A 108.5 . . ?
C16 C15 H15B 108.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
C15 C16 H16A 108.2 . . ?
C15 C16 H16B 108.2 . . ?
C17 C16 C15 116.4(6) . . ?
C17 C16 H16A 108.2 . . ?
C17 C16 H16B 108.2 . . ?
H16A C16 H16B 107.3 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
N6 C12 H12A 107.9 . . ?
N6 C12 H12B 107.9 . . ?
H12A C12 H12B 107.2 . . ?
C13 C12 N6 117.4(5) . . ?
C13 C12 H12A 107.9 . . ?
C13 C12 H12B 107.9 . . ?
C14 C13 H13A 107.9 . . ?
C14 C13 H13B 107.9 . . ?
C12 C13 C14 117.5(6) . . ?
C12 C13 H13A 107.9 . . ?
C12 C13 H13B 107.9 . . ?
H13A C13 H13B 107.2 . . ?

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
Ni1 S4 C6 C8 -179.8(2) . . . . ?
Ni1 S4 C6 C5 -0.1(3) . . . . ?
Ni1 S1 C1 C2 0.0(3) . . . . ?
Ni1 S1 C1 C3 179.1(3) . . . . ?
Ni1 S3 C5 C6 -0.4(3) . . . . ?
Ni1 S3 C5 C7 178.8(3) . . . . ?
Ni1 S2 C2 C1 -0.7(3) . . . . ?
Ni1 S2 C2 C4 179.5(3) . . . . ?
S4 Ni1 S1 C1 178.06(12) . . . . ?
S4 Ni1 S3 C5 0.23(12) . . . . ?
S4 Ni1 S2 C2 -118.7(15) . . . . ?
S4 C6 C5 S3 0.3(4) . . . . ?
S4 C6 C5 C7 -178.8(3) . . . . ?
S1 Ni1 S4 C6 176.78(12) . . . . ?
S1 Ni1 S3 C5 -98.5(9) . . . . ?
S1 Ni1 S2 C2 0.55(13) . . . . ?
S1 C1 C3 N1 153(33) . . . . ?
S3 Ni1 S4 C6 -0.10(12) . . . . ?
S3 Ni1 S1 C1 -83.1(9) . . . . ?
S3 Ni1 S2 C2 177.42(13) . . . . ?
S2 Ni1 S4 C6 -63.9(15) . . . . ?
S2 Ni1 S1 C1 -0.36(12) . . . . ?
S2 Ni1 S3 C5 178.61(12) . . . . ?
S2 C2 C1 S1 0.5(4) . . . . ?
S2 C2 C1 C3 -178.6(3) . . . . ?
S2 C2 C4 N2 -88(31) . . . . ?
N5 C15 C16 C17 -57.7(9) . . . . ?
N6 C10 C11 N5 -0.1(6) . . . . ?
N6 C12 C13 C14 -173.6(5) . . . . ?
C2 C1 C3 N1 -28(33) . . . . ?
C8 C6 C5 S3 180.0(2) . . . . ?
C8 C6 C5 C7 0.9(5) . . . . ?
N3 C7 C5 S3 5(35) . . . . ?
N3 C7 C5 C6 -176(100) . . . . ?
C1 C2 C4 N2 92(31) . . . . ?
C4 C2 C1 S1 -179.7(3) . . . . ?
C4 C2 C1 C3 1.2(6) . . . . ?
N4 C8 C6 S4 -153(14) . . . . ?
N4 C8 C6 C5 27(14) . . . . ?
C10 N6 C9 N5 -0.1(5) . . . . ?
C10 N6 C12 C13 -59.7(8) . . . . ?
C9 N5 C11 C10 0.1(6) . . . . ?
C9 N5 C15 C16 114.2(6) . . . . ?
C9 N6 C10 C11 0.1(6) . . . . ?
C9 N6 C12 C13 121.8(6) . . . . ?
C11 N5 C9 N6 0.0(5) . . . . ?
C11 N5 C15 C16 -66.0(7) . . . . ?
C15 N5 C9 N6 179.8(4) . . . . ?
C15 N5 C11 C10 -179.8(4) . . . . ?
C12 N6 C10 C11 -178.6(5) . . . . ?
C12 N6 C9 N5 178.6(4) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1_tw
_database_code_depnum_ccdc_archive 'CCDC 2076781'
loop_
_audit_author_name
_audit_author_address
'yin qian'
;nanjing tech university
China
;
_audit_update_record             
;
2024-10-02 deposited with the CCDC.	2024-10-21 downloaded from the CCDC.
;
_audit_creation_date             2024-09-17
_audit_creation_method           
;
Olex2 1.5-dev
(compiled 2024.09.12 svn.r2332d2e9 for OlexSys, GUI svn.r6697)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 N4 Ni S4, C9 H17 N2'
_chemical_formula_sum            'C17 H17 N6 Ni S4'
_chemical_formula_weight         492.32
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   20.09(7)
_cell_length_b                   7.18(2)
_cell_length_c                   16.16(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2331(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1109
_cell_measurement_temperature    368(2)
_cell_measurement_theta_max      17.3954
_cell_measurement_theta_min      2.3873
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.869
_exptl_absorpt_coefficient_mu    1.205
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1012
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0572
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            536
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        14.997
_diffrn_reflns_theta_max         14.997
_diffrn_reflns_theta_min         2.387
_diffrn_ambient_temperature      368.15
_diffrn_detector_area_resol_mean 10.42
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                328
_reflns_number_total             536
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         536
_refine_ls_number_restraints     114
_refine_ls_R_factor_all          0.1341
_refine_ls_R_factor_gt           0.0889
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1676P)²+2.9191P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2217
_refine_ls_wR_factor_ref         0.2692
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.41(15)
 0.59(15)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 N6-C12 = N5-C15
 1.4 with sigma of 0.02
 C12-C13 = C13-C14 = C15-C16 = C16-C17
 1.5 with sigma of 0.02
 N5-C11 = C11-C10 = C10-N6 = N6-C9 = C9-N5
 1.39 with sigma of 0.01
 C16-N5 = C15-C17 = C13-N6 = C12-C14
 2.5 with sigma of 0.04
 N5-C10 \\sim C11-N6 \\sim C10-C9 \\sim N6-N5 \\sim C9-C11
 with sigma of 0.02
 C11-C15 \\sim C15-C9
 with sigma of 0.02
 C10-C12 \\sim C12-C9
 with sigma of 0.02
 C17-C16 \\sim C16-C15 \\sim C14-C13 \\sim C13-C12
 with sigma of 0.02
 C15-C17 \\sim C14-C12
 with sigma of 0.02
4. Restrained planarity
 N5, C11, C10, N6, C9
 with sigma of 0.1
5. Rigid bond restraints
 C1, C2, C3, C4, C5, C6, C7, C8, N1, N2, N3, N4
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
6. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim N1
\\sim N2 \\sim N3 \\sim N4: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
Uanis(N5) = Uanis(C9) = Uanis(C11) = Uanis(C15) = Uanis(N6) = Uanis(C10) =
Uanis(C16) = Uanis(C12) = Uanis(C17) = Uanis(C13) = Uanis(C14)
7. Others
 Fixed Sof: N5(0.5) C9(0.5) H9(0.5) N6(0.5) C10(0.5) H10(0.5) C11(0.5)
 H11(0.5) C12(0.5) H12A(0.5) H12B(0.5) C14(0.5) H14A(0.5) H14B(0.5) H14C(0.5)
 C13(0.5) H13A(0.5) H13B(0.5) C15(0.5) H15A(0.5) H15B(0.5) C17(0.5) H17A(0.5)
 H17B(0.5) H17C(0.5) C16(0.5) H16A(0.5) H16B(0.5)
8.a :
 N5(C9,N6,C10,C11)
8.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C15(H15A,H15B), C16(H16A,H16B)
8.c Me refined with riding coordinates:
 C14(H14A,H14B,H14C), C17(H17A,H17B,H17C)
8.d Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.4944(2) 0.750000 0.4334(3) 0.141(3) Uani 1 2 d S T P . .
S1 S 0.4968(5) 0.750000 0.3014(7) 0.162(4) Uani 1 2 d S T P . .
S2 S 0.3885(5) 0.750000 0.4356(9) 0.161(5) Uani 1 2 d S T P . .
S4 S 0.4932(5) 0.750000 0.5654(6) 0.154(5) Uani 1 2 d S T P . .
S3 S 0.5999(5) 0.750000 0.4307(8) 0.159(5) Uani 1 2 d S T P . .
N2 N 0.2529(19) 0.750000 0.295(2) 0.226(12) Uani 1 2 d S TU P . .
N1 N 0.384(2) 0.750000 0.128(3) 0.243(13) Uani 1 2 d S TU P . .
N4 N 0.6063(17) 0.750000 0.739(3) 0.199(11) Uani 1 2 d S TU P . .
N3 N 0.738(2) 0.750000 0.563(2) 0.213(12) Uani 1 2 d S TU P . .
C1 C 0.417(3) 0.750000 0.276(5) 0.223(10) Uani 1 2 d S TU P . .
C2 C 0.377(4) 0.750000 0.328(5) 0.222(10) Uani 1 2 d S TU P . .
C4 C 0.311(3) 0.750000 0.320(3) 0.224(11) Uani 1 2 d S TU P . .
C3 C 0.402(3) 0.750000 0.195(4) 0.226(11) Uani 1 2 d S TU P . .
C6 C 0.576(3) 0.750000 0.587(5) 0.189(10) Uani 1 2 d S TU P . .
C8 C 0.593(2) 0.750000 0.666(4) 0.192(10) Uani 1 2 d S TU P . .
C5 C 0.617(4) 0.750000 0.534(4) 0.192(10) Uani 1 2 d S TU P . .
C7 C 0.679(3) 0.750000 0.550(3) 0.199(10) Uani 1 2 d S TU P . .
N5 N 0.302(2) 0.244(5) 0.051(3) 0.49(4) Uani 0.5 1 d DG . P A -1
C9 C 0.269(3) 0.132(5) 0.108(3) 0.49(4) Uani 0.5 1 d DG . P A -1
H9 H 0.272489 0.003142 0.113006 0.585 Uiso 0.5 1 calc R U P A -1
N6 N 0.229(2) 0.252(7) 0.155(3) 0.49(4) Uani 0.5 1 d DG . P A -1
C10 C 0.236(3) 0.427(6) 0.129(3) 0.49(4) Uani 0.5 1 d DG . P A -1
H10 H 0.215093 0.531829 0.150323 0.585 Uiso 0.5 1 calc R U P A -1
C11 C 0.282(3) 0.427(5) 0.064(3) 0.49(4) Uani 0.5 1 d DG . P A -1
H11 H 0.296630 0.530779 0.035099 0.585 Uiso 0.5 1 calc R U P A -1
C12 C 0.186(3) 0.187(9) 0.217(4) 0.49(4) Uani 0.5 1 d D . P A -1
H12A H 0.213337 0.158626 0.264681 0.585 Uiso 0.5 1 calc R U P A -1
H12B H 0.167755 0.069841 0.197311 0.585 Uiso 0.5 1 calc R U P A -1
C14 C 0.090(3) 0.198(14) 0.309(4) 0.49(4) Uani 0.5 1 d D . P A -1
H14A H 0.052813 0.272242 0.328057 0.731 Uiso 0.5 1 calc R U P A -1
H14B H 0.072968 0.085545 0.284444 0.731 Uiso 0.5 1 calc R U P A -1
H14C H 0.117797 0.167645 0.354972 0.731 Uiso 0.5 1 calc R U P A -1
C13 C 0.129(3) 0.307(12) 0.245(4) 0.49(4) Uani 0.5 1 d D . P A -1
H13A H 0.145555 0.420971 0.269727 0.585 Uiso 0.5 1 calc R U P A -1
H13B H 0.100567 0.338579 0.198948 0.585 Uiso 0.5 1 calc R U P A -1
C15 C 0.351(2) 0.186(7) -0.006(3) 0.49(4) Uani 0.5 1 d D . P A -1
H15A H 0.344716 0.257145 -0.056064 0.585 Uiso 0.5 1 calc R U P A -1
H15B H 0.341644 0.056299 -0.019211 0.585 Uiso 0.5 1 calc R U P A -1
C17 C 0.465(2) 0.152(14) -0.054(4) 0.49(4) Uani 0.5 1 d D . P A -1
H17A H 0.511546 0.161510 -0.038284 0.731 Uiso 0.5 1 calc R U P A -1
H17B H 0.455881 0.027705 -0.071262 0.731 Uiso 0.5 1 calc R U P A -1
H17C H 0.456381 0.237588 -0.097991 0.731 Uiso 0.5 1 calc R U P A -1
C16 C 0.423(3) 0.201(17) 0.020(4) 0.49(4) Uani 0.5 1 d D . P A -1
H16A H 0.431601 0.115801 0.065207 0.585 Uiso 0.5 1 calc R U P A -1
H16B H 0.432103 0.326420 0.038383 0.585 Uiso 0.5 1 calc R U P A -1


_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 S1 2.135(13) . ?
Ni1 S2 2.128(13) . ?
Ni1 S4 2.132(12) . ?
Ni1 S3 2.121(13) . ?
S1 C1 1.66(6) . ?
S2 C2 1.75(7) . ?
S4 C6 1.71(6) . ?
S3 C5 1.70(6) . ?
N2 C4 1.24(5) . ?
N1 C3 1.14(6) . ?
N4 C8 1.21(6) . ?
N3 C7 1.20(5) . ?
C1 C2 1.16(8) . ?
C1 C3 1.34(8) . ?
C2 C4 1.33(6) . ?
C6 C8 1.32(6) . ?
C6 C5 1.18(6) . ?
C5 C7 1.28(5) . ?
N5 C9 1.389(6) . ?
N5 C11 1.389(6) . ?
N5 C15 1.40(2) . ?
C9 N6 1.414(6) . ?
N6 C10 1.337(6) . ?
N6 C12 1.39(2) . ?
C10 C11 1.389(6) . ?
C12 C13 1.512(16) . ?
C14 C13 1.512(16) . ?
C15 C16 1.508(17) . ?
C17 C16 1.509(16) . ?

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
S2 Ni1 S1 92.3(5) . . ?
S2 Ni1 S4 88.5(5) . . ?
S4 Ni1 S1 179.3(5) . . ?
S3 Ni1 S1 87.5(5) . . ?
S3 Ni1 S2 179.7(5) . . ?
S3 Ni1 S4 91.8(5) . . ?
C1 S1 Ni1 103(3) . . ?
C2 S2 Ni1 96(3) . . ?
C6 S4 Ni1 101(3) . . ?
C5 S3 Ni1 100(3) . . ?
C2 C1 S1 119(9) . . ?
C2 C1 C3 124(8) . . ?
C3 C1 S1 117(6) . . ?
C1 C2 S2 130(9) . . ?
C1 C2 C4 128(9) . . ?
C4 C2 S2 103(6) . . ?
N2 C4 C2 166(6) . . ?
N1 C3 C1 175(8) . . ?
C8 C6 S4 116(5) . . ?
C5 C6 S4 121(8) . . ?
C5 C6 C8 122(8) . . ?
N4 C8 C6 179(6) . . ?
C6 C5 S3 125(8) . . ?
C6 C5 C7 122(8) . . ?
C7 C5 S3 113(6) . . ?
N3 C7 C5 179(6) . . ?
C9 N5 C11 108.0 . . ?
C9 N5 C15 126.1(11) . . ?
C11 N5 C15 125.8(10) . . ?
N5 C9 N6 106.1 . . ?
C10 N6 C9 109.5 . . ?
C10 N6 C12 128.2(10) . . ?
C12 N6 C9 122.2(11) . . ?
N6 C10 C11 108.4 . . ?
C10 C11 N5 108.0 . . ?
N6 C12 C13 120(3) . . ?
C14 C13 C12 108(2) . . ?
N5 C15 C16 118(4) . . ?
C15 C16 C17 108(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
Ni1 S1 C1 C2 0.000(7) . . . . ?
Ni1 S1 C1 C3 180.000(2) . . . . ?
Ni1 S2 C2 C1 0.000(10) . . . . ?
Ni1 S2 C2 C4 180.000(4) . . . . ?
Ni1 S4 C6 C8 180.000(8) . . . . ?
Ni1 S4 C6 C5 0.000(14) . . . . ?
Ni1 S3 C5 C6 0.000(14) . . . . ?
Ni1 S3 C5 C7 180.000(7) . . . . ?
S1 C1 C2 S2 0.000(10) . . . . ?
S1 C1 C2 C4 180.000(7) . . . . ?
S2 C2 C4 N2 180.000(16) . . . . ?
S4 C6 C5 S3 0.000(17) . . . . ?
S4 C6 C5 C7 180.000(12) . . . . ?
C1 C2 C4 N2 0.000(17) . . . . ?
C3 C1 C2 S2 180.000(4) . . . . ?
C3 C1 C2 C4 0.000(9) . . . . ?
C8 C6 C5 S3 180.000(11) . . . . ?
C8 C6 C5 C7 0.000(17) . . . . ?
N5 C9 N6 C10 0.4 . . . . ?
N5 C9 N6 C12 178(7) . . . . ?
N5 C15 C16 C17 -173(7) . . . . ?
C9 N5 C11 C10 0.0 . . . . ?
C9 N5 C15 C16 -94(8) . . . . ?
C9 N6 C10 C11 -0.4 . . . . ?
C9 N6 C12 C13 -160(7) . . . . ?
N6 C10 C11 N5 0.2 . . . . ?
N6 C12 C13 C14 177(7) . . . . ?
C10 N6 C12 C13 17(12) . . . . ?
C11 N5 C9 N6 -0.2 . . . . ?
C11 N5 C15 C16 82(8) . . . . ?
C12 N6 C10 C11 -178(7) . . . . ?
C15 N5 C9 N6 176(5) . . . . ?
C15 N5 C11 C10 -176(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.41(15)
2 0.59(15)

