# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_953ns1
_database_code_depnum_ccdc_archive 'CCDC 2031755'
loop_
_audit_author_name
_audit_author_address
'Paul Bernhardt'
;University of Queensland
Australia
;
_audit_update_record             
;
2020-10-24 deposited with the CCDC.	2020-12-01 downloaded from the CCDC.
;

_audit_creation_date             2020-09-14T12:06:58-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C9 H14 N4 Ni S4'
_chemical_formula_weight         365.19
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   7.350(2)
_cell_length_b                   14.101(5)
_cell_length_c                   14.224(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1474.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1150
_cell_measurement_theta_min      3.23
_cell_measurement_theta_max      25.92
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear dark brown'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.879
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.07
_diffrn_orient_matrix_ub_11      0.018657
_diffrn_orient_matrix_ub_12      -0.01808
_diffrn_orient_matrix_ub_13      0.045415
_diffrn_orient_matrix_ub_21      -0.050408
_diffrn_orient_matrix_ub_22      0.037802
_diffrn_orient_matrix_ub_23      0.020151
_diffrn_orient_matrix_ub_31      -0.080097
_diffrn_orient_matrix_ub_32      -0.028005
_diffrn_orient_matrix_ub_33      -0.002108
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  
'Agilent Technologies Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0676
_diffrn_reflns_number            3923
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.889
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_full        24.991
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     1
_reflns_Friedel_coverage         0.718
_reflns_number_total             2400
_reflns_number_gt                2151
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
'CrysalisPro  Version 1.171.36.28 (Agilent Technologies, 2013)'
_computing_cell_refinement       
'CrysalisPro  Version 1.171.36.28 (Agilent Technologies, 2013)'
_computing_data_reduction        
'CrysalisPro  Version 1.171.36.28 (Agilent Technologies, 2013)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/1
_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)+(0.0275P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2400
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.04
_refine_ls_wR_factor_ref         0.0811
_refine_ls_wR_factor_gt          0.077
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.992
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.31(3)
_refine_diff_density_max         0.43
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.075

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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
C1 C 0.4717(8) -0.1240(5) 0.0073(4) 0.0271(16) Uani 1 1 d . . . . .
C2 C 0.4792(9) -0.0088(5) -0.2024(4) 0.0273(16) Uani 1 1 d . . . . .
C3 C 0.6446(8) 0.0529(5) -0.1877(4) 0.0265(15) Uani 1 1 d . . . . .
H3A H 0.733663 0.017245 -0.149301 0.032 Uiso 1 1 calc R U . . .
H3B H 0.701399 0.064919 -0.249718 0.032 Uiso 1 1 calc R U . . .
C4 C 0.6097(8) 0.1466(4) -0.1410(4) 0.0268(15) Uani 1 1 d . . . . .
C5 C 0.5971(9) 0.2397(4) 0.0767(4) 0.0251(14) Uani 1 1 d . . . . .
C6 C 0.3706(11) -0.2873(6) 0.0925(5) 0.057(2) Uani 1 1 d . . . . .
H6A H 0.497656 -0.291121 0.113023 0.085 Uiso 1 1 calc R U . . .
H6B H 0.320818 -0.351485 0.086046 0.085 Uiso 1 1 calc R U . . .
H6C H 0.299579 -0.252027 0.139115 0.085 Uiso 1 1 calc R U . . .
C7 C 0.3908(10) -0.0056(5) -0.2961(4) 0.041(2) Uani 1 1 d . . . . .
H7A H 0.475313 -0.029764 -0.343689 0.061 Uiso 1 1 calc R U . . .
H7B H 0.357875 0.059977 -0.311115 0.061 Uiso 1 1 calc R U . . .
H7C H 0.280938 -0.044984 -0.295283 0.061 Uiso 1 1 calc R U . . .
C8 C 0.6024(10) 0.2333(4) -0.1995(4) 0.0367(17) Uani 1 1 d . . . . .
H8A H 0.515472 0.278178 -0.172057 0.055 Uiso 1 1 calc R U . . .
H8B H 0.563549 0.216695 -0.263307 0.055 Uiso 1 1 calc R U . . .
H8C H 0.723295 0.262533 -0.201824 0.055 Uiso 1 1 calc R U . . .
C9 C 0.5847(10) 0.4308(4) 0.0463(4) 0.0388(16) Uani 1 1 d . . . . .
H9A H 0.685944 0.421295 0.002419 0.058 Uiso 1 1 calc R U . . .
H9B H 0.590818 0.495086 0.072355 0.058 Uiso 1 1 calc R U . . .
H9C H 0.469161 0.422568 0.01287 0.058 Uiso 1 1 calc R U . . .
N1 N 0.5003(7) -0.0554(4) -0.0529(3) 0.0238(12) Uani 1 1 d . . . . .
N2 N 0.4138(7) -0.0630(4) -0.1400(3) 0.0274(12) Uani 1 1 d . . . . .
N3 N 0.5939(7) 0.1483(4) -0.0505(3) 0.0240(12) Uani 1 1 d . . . . .
N4 N 0.5801(8) 0.2408(4) -0.0123(3) 0.0269(12) Uani 1 1 d . . . . .
S1 S 0.5582(3) -0.08956(13) 0.11465(10) 0.0345(4) Uani 1 1 d . . . . .
S2 S 0.6189(2) 0.13728(13) 0.14513(10) 0.0343(5) Uani 1 1 d . . . . .
S3 S 0.3591(3) -0.22749(14) -0.01900(12) 0.0444(5) Uani 1 1 d . . . . .
S4 S 0.5997(2) 0.34626(13) 0.13942(11) 0.0350(4) Uani 1 1 d . . . . .
Ni1 Ni 0.57836(11) 0.04213(6) 0.03026(5) 0.0243(2) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 N1 1.308(8) . ?
C1 S3 1.719(7) . ?
C1 S1 1.724(6) . ?
C1 Ni1 2.491(7) . ?
C2 N2 1.264(8) . ?
C2 C7 1.483(8) . ?
C2 C3 1.510(8) . ?
C3 C4 1.501(8) . ?
C4 N3 1.294(7) . ?
C4 C8 1.480(8) . ?
C5 N4 1.271(7) . ?
C5 S4 1.748(6) . ?
C5 S2 1.749(6) . ?
C6 S3 1.798(7) . ?
C9 S4 1.786(6) . ?
N1 N2 1.397(6) . ?
N1 Ni1 1.903(5) . ?
N3 N4 1.416(7) . ?
N3 Ni1 1.891(5) . ?
S1 Ni1 2.2161(19) . ?
S2 Ni1 2.1351(18) . ?

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 C1 S3 124.2(4) . . ?
N1 C1 S1 108.2(5) . . ?
S3 C1 S1 127.5(4) . . ?
N1 C1 Ni1 48.7(3) . . ?
S3 C1 Ni1 168.0(3) . . ?
S1 C1 Ni1 60.2(2) . . ?
N2 C2 C7 118.8(6) . . ?
N2 C2 C3 123.9(5) . . ?
C7 C2 C3 117.3(6) . . ?
C4 C3 C2 115.5(5) . . ?
N3 C4 C8 122.7(5) . . ?
N3 C4 C3 118.2(5) . . ?
C8 C4 C3 119.0(5) . . ?
N4 C5 S4 119.9(5) . . ?
N4 C5 S2 125.0(5) . . ?
S4 C5 S2 115.1(3) . . ?
C1 N1 N2 116.8(5) . . ?
C1 N1 Ni1 100.1(3) . . ?
N2 N1 Ni1 138.0(4) . . ?
C2 N2 N1 113.8(5) . . ?
C4 N3 N4 114.0(5) . . ?
C4 N3 Ni1 126.5(4) . . ?
N4 N3 Ni1 119.5(3) . . ?
C5 N4 N3 111.3(5) . . ?
C1 S1 Ni1 77.3(2) . . ?
C5 S2 Ni1 94.59(19) . . ?
C1 S3 C6 100.6(3) . . ?
C5 S4 C9 101.2(3) . . ?
N3 Ni1 N1 102.3(2) . . ?
N3 Ni1 S2 87.61(15) . . ?
N1 Ni1 S2 166.44(16) . . ?
N3 Ni1 S1 175.40(14) . . ?
N1 Ni1 S1 73.18(16) . . ?
S2 Ni1 S1 96.98(7) . . ?
N3 Ni1 C1 133.17(19) . . ?
N1 Ni1 C1 31.11(18) . . ?
S2 Ni1 C1 137.32(14) . . ?
S1 Ni1 C1 42.46(13) . . ?



# END of CIF
####################################################################### 
# 
# 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_954ns2
_database_code_depnum_ccdc_archive 'CCDC 2031756'
loop_
_audit_author_name
_audit_author_address
'Paul Bernhardt'
;University of Queensland
Australia
;
_audit_update_record             
;
2020-10-24 deposited with the CCDC.	2020-12-01 downloaded from the CCDC.
;

_audit_creation_date             2020-09-14T12:16:09-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C9 H14 N4 Ni S4'
_chemical_formula_weight         365.19

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_Int_Tables_number      33
loop_
_symmetry_equiv_pos_as_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                   7.698(2)
_cell_length_b                   21.736(5)
_cell_length_c                   8.525(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1426.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    897
_cell_measurement_theta_min      3.21
_cell_measurement_theta_max      26.37
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.54
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.07
_diffrn_orient_matrix_ub_11      -0.03465
_diffrn_orient_matrix_ub_12      -0.028382
_diffrn_orient_matrix_ub_13      0.026861
_diffrn_orient_matrix_ub_21      0.06588
_diffrn_orient_matrix_ub_22      -0.001606
_diffrn_orient_matrix_ub_23      0.05791
_diffrn_orient_matrix_ub_31      -0.054454
_diffrn_orient_matrix_ub_32      0.016044
_diffrn_orient_matrix_ub_33      0.053045
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  
'Agilent Technologies Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_av_unetI/netI     0.0785
_diffrn_reflns_number            3394
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.243
_diffrn_reflns_theta_max         24.976
_diffrn_reflns_theta_full        24.976
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_coverage         0.864
_reflns_number_total             1817
_reflns_number_gt                1579
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
'CrysalisPro  Version 1.171.36.28 (Agilent Technologies, 2013)'
_computing_cell_refinement       
'CrysalisPro  Version 1.171.36.28 (Agilent Technologies, 2013)'
_computing_data_reduction        
'CrysalisPro  Version 1.171.36.28 (Agilent Technologies, 2013)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/1
_refine_special_details          'Refined as a 2-component inversion twin.,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)+(0.0611P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1817
_refine_ls_number_parameters     168
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.05
_refine_ls_wR_factor_ref         0.1193
_refine_ls_wR_factor_gt          0.113
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_restrained_S_all      0.978
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.56(5)
_refine_diff_density_max         0.659
_refine_diff_density_min         -0.622
_refine_diff_density_rms         0.107

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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
C1 C 0.4151(12) 0.7772(4) 0.6305(10) 0.024(2) Uani 1 1 d . . . . .
C2 C 0.3048(13) 0.7075(4) 0.2898(12) 0.029(2) Uani 1 1 d . . . . .
C3 C 0.4202(13) 0.6524(4) 0.2980(11) 0.027(2) Uani 1 1 d . . . . .
H3A H 0.447577 0.638882 0.189949 0.033 Uiso 1 1 calc R U . . .
H3B H 0.530666 0.664374 0.34904 0.033 Uiso 1 1 calc R U . . .
C4 C 0.3432(13) 0.5997(4) 0.3857(11) 0.027(2) Uani 1 1 d . . . . .
C5 C 0.3152(14) 0.5432(4) 0.7489(13) 0.029(2) Uani 1 1 d . . . . .
C6 C 0.4117(14) 0.8878(5) 0.7749(16) 0.049(3) Uani 1 1 d . . . . .
H6A H 0.325005 0.875607 0.853098 0.073 Uiso 1 1 calc R U . . .
H6B H 0.409869 0.932666 0.762531 0.073 Uiso 1 1 calc R U . . .
H6C H 0.527275 0.874803 0.809797 0.073 Uiso 1 1 calc R U . . .
C7 C 0.2001(14) 0.7167(4) 0.1468(13) 0.040(3) Uani 1 1 d . . . . .
H7A H 0.112133 0.684239 0.139318 0.06 Uiso 1 1 calc R U . . .
H7B H 0.275938 0.715057 0.054545 0.06 Uiso 1 1 calc R U . . .
H7C H 0.142793 0.756902 0.151507 0.06 Uiso 1 1 calc R U . . .
C8 C 0.2708(15) 0.5470(4) 0.2935(14) 0.037(3) Uani 1 1 d . . . . .
H8A H 0.341973 0.510319 0.311441 0.055 Uiso 1 1 calc R U . . .
H8B H 0.271846 0.557332 0.181589 0.055 Uiso 1 1 calc R U . . .
H8C H 0.151231 0.538947 0.327122 0.055 Uiso 1 1 calc R U . . .
C9 C 0.1882(15) 0.4274(4) 0.6960(13) 0.045(3) Uani 1 1 d . . . . .
H9A H 0.08301 0.444247 0.647458 0.068 Uiso 1 1 calc R U . . .
H9B H 0.163383 0.386355 0.737927 0.068 Uiso 1 1 calc R U . . .
H9C H 0.280501 0.42455 0.617214 0.068 Uiso 1 1 calc R U . . .
N1 N 0.3891(11) 0.7334(3) 0.5304(9) 0.0263(19) Uani 1 1 d . . . . .
N2 N 0.2960(11) 0.7477(3) 0.3967(9) 0.0280(19) Uani 1 1 d . . . . .
N3 N 0.3468(11) 0.5989(3) 0.5374(9) 0.0271(19) Uani 1 1 d . . . . .
N4 N 0.2827(11) 0.5448(3) 0.6009(10) 0.030(2) Uani 1 1 d . . . . .
Ni1 Ni 0.41836(16) 0.66440(5) 0.66529(15) 0.0258(3) Uani 1 1 d . . . . .
S1 S 0.4989(4) 0.74697(11) 0.7986(3) 0.0317(6) Uani 1 1 d . . . . .
S2 S 0.4166(4) 0.59998(11) 0.8544(3) 0.0332(7) Uani 1 1 d . . . . .
S3 S 0.3626(4) 0.85239(11) 0.5922(4) 0.0413(7) Uani 1 1 d . . . . .
S4 S 0.2569(4) 0.47693(11) 0.8522(3) 0.0386(7) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 N1 1.294(11) . ?
C1 S1 1.704(9) . ?
C1 S3 1.714(9) . ?
C1 Ni1 2.470(8) . ?
C2 N2 1.265(12) . ?
C2 C7 1.475(13) . ?
C2 C3 1.491(13) . ?
C3 C4 1.491(13) . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C4 N3 1.294(12) . ?
C4 C8 1.497(13) . ?
C5 N4 1.287(12) . ?
C5 S2 1.715(10) . ?
C5 S4 1.747(10) . ?
C6 S3 1.779(12) . ?
C6 H6A 0.98 . ?
C6 H6B 0.98 . ?
C6 H6C 0.98 . ?
C7 H7A 0.98 . ?
C7 H7B 0.98 . ?
C7 H7C 0.98 . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
C9 S4 1.792(11) . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
N1 N2 1.381(11) . ?
N1 Ni1 1.904(8) . ?
N3 N4 1.385(10) . ?
N3 Ni1 1.876(8) . ?
Ni1 S2 2.135(3) . ?
Ni1 S1 2.213(3) . ?

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 C1 S1 109.2(6) . . ?
N1 C1 S3 122.6(7) . . ?
S1 C1 S3 128.1(5) . . ?
N1 C1 Ni1 49.5(4) . . ?
S1 C1 Ni1 60.8(3) . . ?
S3 C1 Ni1 166.2(5) . . ?
N2 C2 C7 118.2(8) . . ?
N2 C2 C3 123.5(9) . . ?
C7 C2 C3 118.2(9) . . ?
C4 C3 C2 113.8(9) . . ?
C4 C3 H3A 108.8 . . ?
C2 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
C2 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
N3 C4 C3 120.2(9) . . ?
N3 C4 C8 121.5(9) . . ?
C3 C4 C8 118.2(9) . . ?
N4 C5 S2 125.6(8) . . ?
N4 C5 S4 117.8(8) . . ?
S2 C5 S4 116.5(6) . . ?
S3 C6 H6A 109.5 . . ?
S3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
S3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
S4 C9 H9A 109.5 . . ?
S4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
S4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C1 N1 N2 117.3(8) . . ?
C1 N1 Ni1 99.4(6) . . ?
N2 N1 Ni1 137.4(6) . . ?
C2 N2 N1 114.3(8) . . ?
C4 N3 N4 113.2(8) . . ?
C4 N3 Ni1 125.2(7) . . ?
N4 N3 Ni1 121.5(6) . . ?
C5 N4 N3 109.7(8) . . ?
N3 Ni1 N1 102.3(3) . . ?
N3 Ni1 S2 86.5(2) . . ?
N1 Ni1 S2 166.4(3) . . ?
N3 Ni1 S1 175.1(2) . . ?
N1 Ni1 S1 72.8(2) . . ?
S2 Ni1 S1 98.39(12) . . ?
N3 Ni1 C1 132.9(3) . . ?
N1 Ni1 C1 31.1(3) . . ?
S2 Ni1 C1 137.9(2) . . ?
S1 Ni1 C1 42.2(2) . . ?
C1 S1 Ni1 77.0(3) . . ?
C5 S2 Ni1 94.5(4) . . ?
C1 S3 C6 101.3(5) . . ?
C5 S4 C9 101.3(5) . . ?



# END of CIF
####################################################################### 
# 
# 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_1817jb21
_database_code_depnum_ccdc_archive 'CCDC 2031757'
loop_
_audit_author_name
_audit_author_address
'Paul Bernhardt'
;University of Queensland
Australia
;
_audit_update_record             
;
2020-10-24 deposited with the CCDC.	2020-12-01 downloaded from the CCDC.
;

_audit_creation_date             2020-09-14T12:29:04-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C9 H14 N4 Ni S4'
_chemical_formula_weight         365.19

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6588(7)
_cell_length_b                   8.7590(10)
_cell_length_c                   11.3774(9)
_cell_angle_alpha                104.320(8)
_cell_angle_beta                 104.614(8)
_cell_angle_gamma                96.573(8)
_cell_volume                     702.75(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    2289
_cell_measurement_theta_min      5.3
_cell_measurement_theta_max      62.6
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear orange'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    7.442
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.768
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.02
_diffrn_orient_matrix_ub_11      -0.078025
_diffrn_orient_matrix_ub_12      -0.179984
_diffrn_orient_matrix_ub_13      -0.030115
_diffrn_orient_matrix_ub_21      0.191823
_diffrn_orient_matrix_ub_22      -0.027438
_diffrn_orient_matrix_ub_23      0.063928
_diffrn_orient_matrix_ub_31      -0.043826
_diffrn_orient_matrix_ub_32      0.032025
_diffrn_orient_matrix_ub_33      0.12785
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  
'Agilent Technologies Xcalibur, EosS2, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_number            4193
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.192
_diffrn_reflns_theta_max         62.392
_diffrn_reflns_theta_full        62.392
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_reflns_Friedel_coverage         0
_reflns_number_total             2211
_reflns_number_gt                2000
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysalisPro (Agilent Technologies,     )'
_computing_cell_refinement       'CrysalisPro (Agilent Technologies,     )'
_computing_data_reduction        'CrysalisPro (Agilent Technologies,     )'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/1
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0752P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2211
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1196
_refine_ls_wR_factor_gt          0.115
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.874
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.115

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'
Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.4085(4) 0.9026(4) 0.6689(3) 0.0306(7) Uani 1 1 d . . . . .
C2 C 0.3259(4) 1.2222(4) 0.5635(3) 0.0312(7) Uani 1 1 d . . . . .
C3 C 0.2232(5) 1.2741(4) 0.4552(3) 0.0336(7) Uani 1 1 d . . . . .
H3A H 0.147652 1.348169 0.489241 0.04 Uiso 1 1 calc R U . . .
H3B H 0.316153 1.339719 0.432176 0.04 Uiso 1 1 calc R U . . .
C4 C 0.1000(4) 1.1626(4) 0.3339(3) 0.0320(7) Uani 1 1 d . . . . .
C5 C -0.0814(4) 0.7724(4) 0.1748(3) 0.0291(7) Uani 1 1 d . . . . .
C6 C 0.6513(5) 1.0314(4) 0.9085(3) 0.0416(8) Uani 1 1 d . . . . .
H6A H 0.731429 1.0862 0.870739 0.062 Uiso 1 1 calc R U . . .
H6B H 0.725787 1.012998 0.985709 0.062 Uiso 1 1 calc R U . . .
H6C H 0.562991 1.098079 0.929843 0.062 Uiso 1 1 calc R U . . .
C7 C 0.4411(5) 1.3566(4) 0.6766(3) 0.0368(8) Uani 1 1 d . . . . .
H7A H 0.399329 1.352895 0.750618 0.055 Uiso 1 1 calc R U . . .
H7B H 0.428893 1.459615 0.659104 0.055 Uiso 1 1 calc R U . . .
H7C H 0.570108 1.345027 0.69369 0.055 Uiso 1 1 calc R U . . .
C8 C 0.0146(5) 1.2414(5) 0.2374(3) 0.0411(8) Uani 1 1 d . . . . .
H8A H 0.05137 1.202809 0.160442 0.062 Uiso 1 1 calc R U . . .
H8B H 0.055692 1.357914 0.271417 0.062 Uiso 1 1 calc R U . . .
H8C H -0.119508 1.215155 0.216981 0.062 Uiso 1 1 calc R U . . .
C9 C -0.2412(5) 0.4571(4) 0.0267(3) 0.0416(8) Uani 1 1 d . . . . .
H9A H -0.11581 0.43581 0.044187 0.062 Uiso 1 1 calc R U . . .
H9B H -0.315719 0.386613 -0.056447 0.062 Uiso 1 1 calc R U . . .
H9C H -0.294979 0.43673 0.092249 0.062 Uiso 1 1 calc R U . . .
N1 N 0.4235(4) 1.0504(3) 0.6734(2) 0.0317(6) Uani 1 1 d . . . . .
N2 N 0.3143(3) 1.0736(3) 0.5602(2) 0.0293(6) Uani 1 1 d . . . . .
N3 N 0.0688(3) 1.0091(3) 0.3144(2) 0.0285(6) Uani 1 1 d . . . . .
N4 N -0.0562(4) 0.9249(4) 0.1944(3) 0.0338(6) Uani 1 1 d . . . . .
S1 S 0.27577(11) 0.74310(10) 0.54079(7) 0.0328(3) Uani 1 1 d . . . . .
S2 S 0.02538(11) 0.67660(10) 0.28081(7) 0.0339(2) Uani 1 1 d . . . . .
S3 S 0.52939(11) 0.84192(10) 0.79716(7) 0.0353(3) Uani 1 1 d . . . . .
S4 S -0.23617(11) 0.66368(10) 0.02721(7) 0.0386(3) Uani 1 1 d . . . . .
Ni1 Ni 0.17329(6) 0.89252(6) 0.42515(4) 0.0271(2) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 N1 1.273(4) . ?
C1 S1 1.741(3) . ?
C1 S3 1.756(3) . ?
C2 N2 1.285(4) . ?
C2 C3 1.488(5) . ?
C2 C7 1.504(5) . ?
C3 C4 1.488(5) . ?
C4 N3 1.290(4) . ?
C4 C8 1.492(5) . ?
C5 N4 1.281(5) . ?
C5 S2 1.729(3) . ?
C5 S4 1.755(3) . ?
C6 S3 1.800(4) . ?
C9 S4 1.804(4) . ?
N1 N2 1.422(4) . ?
N2 Ni1 1.899(3) . ?
N3 N4 1.416(4) . ?
N3 Ni1 1.894(3) . ?
S1 Ni1 2.1508(9) . ?
S2 Ni1 2.1427(9) . ?

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 C1 S1 125.6(3) . . ?
N1 C1 S3 121.0(2) . . ?
S1 C1 S3 113.4(2) . . ?
N2 C2 C3 122.1(3) . . ?
N2 C2 C7 123.0(3) . . ?
C3 C2 C7 114.8(3) . . ?
C4 C3 C2 124.3(3) . . ?
N3 C4 C3 122.3(3) . . ?
N3 C4 C8 122.7(3) . . ?
C3 C4 C8 115.1(3) . . ?
N4 C5 S2 124.6(2) . . ?
N4 C5 S4 114.1(2) . . ?
S2 C5 S4 121.3(2) . . ?
C1 N1 N2 112.1(3) . . ?
C2 N2 N1 113.0(3) . . ?
C2 N2 Ni1 127.5(2) . . ?
N1 N2 Ni1 119.5(2) . . ?
C4 N3 N4 113.4(3) . . ?
C4 N3 Ni1 127.3(2) . . ?
N4 N3 Ni1 119.3(2) . . ?
C5 N4 N3 112.7(3) . . ?
C1 S1 Ni1 94.68(12) . . ?
C5 S2 Ni1 95.34(11) . . ?
C1 S3 C6 101.69(17) . . ?
C5 S4 C9 103.86(17) . . ?
N3 Ni1 N2 96.42(12) . . ?
N3 Ni1 S2 88.07(8) . . ?
N2 Ni1 S2 175.46(9) . . ?
N3 Ni1 S1 175.32(9) . . ?
N2 Ni1 S1 88.14(9) . . ?
S2 Ni1 S1 87.38(4) . . ?



# END of CIF
####################################################################### 
# 
# 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_1910jb21
_database_code_depnum_ccdc_archive 'CCDC 2031758'
loop_
_audit_author_name
_audit_author_address
'Paul Bernhardt'
;University of Queensland
Australia
;
_audit_update_record             
;
2020-10-24 deposited with the CCDC.	2020-12-01 downloaded from the CCDC.
;

_audit_creation_date             2020-09-14T12:41:29-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C21 H22 N4 Ni S4'
_chemical_formula_weight         517.37

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.0771(2)
_cell_length_b                   9.8592(2)
_cell_length_c                   25.5079(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.450(2)
_cell_angle_gamma                90
_cell_volume                     2278.64(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    4728
_cell_measurement_theta_min      4.8
_cell_measurement_theta_max      61.34
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    4.781
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.779
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.02
_diffrn_orient_matrix_ub_11      -0.019952
_diffrn_orient_matrix_ub_12      -0.144614
_diffrn_orient_matrix_ub_13      0.021392
_diffrn_orient_matrix_ub_21      0.150887
_diffrn_orient_matrix_ub_22      0.010234
_diffrn_orient_matrix_ub_23      0.030754
_diffrn_orient_matrix_ub_31      -0.075651
_diffrn_orient_matrix_ub_32      0.058486
_diffrn_orient_matrix_ub_33      0.047506
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  
'Agilent Technologies Xcalibur, EosS2, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_number            11251
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.472
_diffrn_reflns_theta_max         61.608
_diffrn_reflns_theta_full        61.608
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_coverage         0
_reflns_number_total             3547
_reflns_number_gt                3074
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysalisPro (Agilent Technologies,     )'
_computing_cell_refinement       'CrysalisPro (Agilent Technologies,     )'
_computing_data_reduction        'CrysalisPro (Agilent Technologies,     )'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/1
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0594P)²+0.4874P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3547
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.049
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1122
_refine_ls_wR_factor_gt          0.1058
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_restrained_S_all      1.06
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.39
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.069

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'
Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.4338(3) 0.2434(3) 0.46217(11) 0.0300(7) Uani 1 1 d . . . . .
C2 C 0.3323(3) -0.0765(3) 0.42681(11) 0.0291(6) Uani 1 1 d . . . . .
C3 C 0.2479(3) -0.1986(3) 0.44257(11) 0.0312(7) Uani 1 1 d . . . . .
H3A H 0.318885 -0.274986 0.444269 0.037 Uiso 1 1 calc R U . . .
H3B H 0.175556 -0.218513 0.41297 0.037 Uiso 1 1 calc R U . . .
C4 C 0.1651(3) -0.2066(3) 0.49145(11) 0.0287(6) Uani 1 1 d . . . . .
C5 C 0.0721(3) -0.0357(3) 0.59984(11) 0.0277(6) Uani 1 1 d . . . . .
C6 C 0.6147(4) 0.3335(4) 0.38469(12) 0.0438(9) Uani 1 1 d . . . . .
H6A H 0.704368 0.388331 0.380022 0.053 Uiso 1 1 calc R U . . .
H6B H 0.645833 0.237529 0.38802 0.053 Uiso 1 1 calc R U . . .
C7 C 0.5134(3) 0.3476(3) 0.33583(11) 0.0348(7) Uani 1 1 d . . . . .
C8 C 0.5206(4) 0.2525(4) 0.29606(13) 0.0453(8) Uani 1 1 d . . . . .
H8 H 0.583374 0.175872 0.300944 0.054 Uiso 1 1 calc R U . . .
C9 C 0.4366(4) 0.2683(5) 0.24908(14) 0.0551(10) Uani 1 1 d . . . . .
H9 H 0.443479 0.203346 0.221836 0.066 Uiso 1 1 calc R U . . .
C10 C 0.3444(4) 0.3768(4) 0.24197(14) 0.0518(10) Uani 1 1 d . . . . .
H10 H 0.287649 0.387668 0.209723 0.062 Uiso 1 1 calc R U . . .
C11 C 0.3337(4) 0.4705(4) 0.28143(15) 0.0519(9) Uani 1 1 d . . . . .
H11 H 0.267971 0.545066 0.276639 0.062 Uiso 1 1 calc R U . . .
C12 C 0.4182(4) 0.4567(4) 0.32821(13) 0.0446(8) Uani 1 1 d . . . . .
H12 H 0.410921 0.52235 0.355187 0.054 Uiso 1 1 calc R U . . .
C13 C 0.4061(4) -0.0906(4) 0.37598(12) 0.0384(8) Uani 1 1 d . . . . .
H13A H 0.377868 -0.014232 0.352919 0.058 Uiso 1 1 d R U . . .
H13B H 0.375071 -0.175784 0.358869 0.058 Uiso 1 1 d R U . . .
H13C H 0.513418 -0.090996 0.382979 0.058 Uiso 1 1 d R U . . .
C14 C 0.0885(4) -0.3385(3) 0.49924(12) 0.0352(7) Uani 1 1 d . . . . .
H14A H 0.10952 -0.369843 0.535378 0.053 Uiso 1 1 d R U . . .
H14B H 0.123838 -0.406036 0.474737 0.053 Uiso 1 1 d R U . . .
H14C H -0.018185 -0.326299 0.492704 0.053 Uiso 1 1 d R U . . .
C15 C -0.1197(4) -0.2034(3) 0.65195(13) 0.0387(8) Uani 1 1 d . . . . .
H15A H -0.2007 -0.20205 0.676263 0.046 Uiso 1 1 calc R U . . .
H15B H -0.165211 -0.212587 0.615874 0.046 Uiso 1 1 calc R U . . .
C16 C -0.0264(3) -0.3263(3) 0.66395(11) 0.0300(7) Uani 1 1 d . . . . .
C17 C -0.0416(4) -0.4378(4) 0.63114(14) 0.0422(8) Uani 1 1 d . . . . .
H17 H -0.106724 -0.433177 0.600608 0.051 Uiso 1 1 calc R U . . .
C18 C 0.0356(4) -0.5547(4) 0.64198(17) 0.0549(10) Uani 1 1 d . . . . .
H18 H 0.024208 -0.629858 0.618796 0.066 Uiso 1 1 calc R U . . .
C19 C 0.1292(4) -0.5642(4) 0.68594(17) 0.0549(10) Uani 1 1 d . . . . .
H19 H 0.180676 -0.646366 0.693638 0.066 Uiso 1 1 calc R U . . .
C019 C 0.0703(4) -0.3350(4) 0.70813(12) 0.0409(8) Uani 1 1 d . . . . .
H019 H 0.08316 -0.259246 0.730987 0.049 Uiso 1 1 calc R U . . .
C20 C 0.1486(4) -0.4541(4) 0.71907(14) 0.0509(10) Uani 1 1 d . . . . .
H20 H 0.215129 -0.459653 0.749207 0.061 Uiso 1 1 calc R U . . .
N1 N 0.4293(3) 0.1354(3) 0.43362(9) 0.0315(6) Uani 1 1 d . . . . .
N2 N 0.3410(3) 0.0328(3) 0.45527(9) 0.0284(5) Uani 1 1 d . . . . .
N3 N 0.1582(3) -0.1063(2) 0.52357(9) 0.0262(5) Uani 1 1 d . . . . .
N4 N 0.0709(3) -0.1354(3) 0.56692(9) 0.0296(6) Uani 1 1 d . . . . .
S1 S 0.34391(9) 0.26467(8) 0.51934(3) 0.0361(2) Uani 1 1 d . . . . .
S2 S 0.16504(9) 0.11534(8) 0.59284(3) 0.0332(2) Uani 1 1 d . . . . .
S3 S 0.53766(9) 0.38438(9) 0.44534(3) 0.0401(2) Uani 1 1 d . . . . .
S4 S -0.02457(9) -0.04208(8) 0.65680(3) 0.0378(2) Uani 1 1 d . . . . .
Ni1 Ni 0.25167(5) 0.06462(5) 0.51910(2) 0.02526(17) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 N1 1.289(4) . ?
C1 S1 1.726(3) . ?
C1 S3 1.747(3) . ?
C2 N2 1.299(4) . ?
C2 C3 1.496(4) . ?
C2 C13 1.501(4) . ?
C3 C4 1.496(4) . ?
C4 N3 1.288(4) . ?
C4 C14 1.494(4) . ?
C5 N4 1.293(4) . ?
C5 S2 1.726(3) . ?
C5 S4 1.743(3) . ?
C6 C7 1.510(5) . ?
C6 S3 1.807(3) . ?
C7 C8 1.386(5) . ?
C7 C12 1.386(5) . ?
C8 C9 1.390(5) . ?
C9 C10 1.364(6) . ?
C10 C11 1.374(6) . ?
C11 C12 1.386(5) . ?
C15 C16 1.499(5) . ?
C15 S4 1.810(3) . ?
C16 C17 1.383(5) . ?
C16 C019 1.389(5) . ?
C17 C18 1.368(5) . ?
C18 C19 1.369(6) . ?
C19 C20 1.380(6) . ?
C019 C20 1.393(5) . ?
N1 N2 1.422(3) . ?
N2 Ni1 1.888(2) . ?
N3 N4 1.428(3) . ?
N3 Ni1 1.893(2) . ?
S1 Ni1 2.1425(9) . ?
S2 Ni1 2.1411(8) . ?

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 C1 S1 125.2(2) . . ?
N1 C1 S3 121.2(2) . . ?
S1 C1 S3 113.61(17) . . ?
N2 C2 C3 122.2(2) . . ?
N2 C2 C13 123.0(3) . . ?
C3 C2 C13 114.8(3) . . ?
C2 C3 C4 123.9(3) . . ?
N3 C4 C14 122.9(2) . . ?
N3 C4 C3 122.4(3) . . ?
C14 C4 C3 114.7(2) . . ?
N4 C5 S2 125.0(2) . . ?
N4 C5 S4 122.0(2) . . ?
S2 C5 S4 113.03(16) . . ?
C7 C6 S3 115.7(2) . . ?
C8 C7 C12 118.6(3) . . ?
C8 C7 C6 119.3(3) . . ?
C12 C7 C6 122.0(3) . . ?
C7 C8 C9 120.5(4) . . ?
C10 C9 C8 120.2(4) . . ?
C9 C10 C11 120.0(4) . . ?
C10 C11 C12 120.3(4) . . ?
C11 C12 C7 120.3(3) . . ?
C16 C15 S4 115.8(2) . . ?
C17 C16 C019 118.5(3) . . ?
C17 C16 C15 119.0(3) . . ?
C019 C16 C15 122.5(3) . . ?
C18 C17 C16 121.0(3) . . ?
C17 C18 C19 120.6(4) . . ?
C18 C19 C20 119.9(4) . . ?
C16 C019 C20 120.3(3) . . ?
C19 C20 C019 119.7(3) . . ?
C1 N1 N2 111.6(2) . . ?
C2 N2 N1 112.9(2) . . ?
C2 N2 Ni1 127.2(2) . . ?
N1 N2 Ni1 119.86(18) . . ?
C4 N3 N4 112.9(2) . . ?
C4 N3 Ni1 127.31(19) . . ?
N4 N3 Ni1 119.80(17) . . ?
C5 N4 N3 111.6(2) . . ?
C1 S1 Ni1 95.18(11) . . ?
C5 S2 Ni1 95.58(10) . . ?
C1 S3 C6 103.42(16) . . ?
C5 S4 C15 103.69(14) . . ?
N2 Ni1 N3 96.97(10) . . ?
N2 Ni1 S2 174.69(8) . . ?
N3 Ni1 S2 88.02(7) . . ?
N2 Ni1 S1 88.12(8) . . ?
N3 Ni1 S1 174.68(7) . . ?
S2 Ni1 S1 86.94(3) . . ?



# END of CIF
