# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1509619'
_audit_update_record             
;
2016-10-12 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H26 N4 Ni S4'
_chemical_formula_sum            'C14 H26 N4 Ni S4'
_chemical_formula_weight         437.32

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      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                   6.5759(4)
_cell_length_b                   8.4895(5)
_cell_length_c                   8.8346(5)
_cell_angle_alpha                84.185(2)
_cell_angle_beta                 78.947(3)
_cell_angle_gamma                80.038(3)
_cell_volume                     475.57(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2259
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      28.0

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_F_000             230
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.462
_shelx_estimated_absorpt_T_min   0.844
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6916
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS, Bruker 2012'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Incoatec microsource'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8678
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.355
_diffrn_reflns_theta_max         28.019
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             2259
_reflns_number_gt                2174
_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       'APEX2 (Bruker, 2012)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2012)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2012)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'WinGX (Farrugia, 2012)'
_computing_publication_material  ?
_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)+(0.0218P)²+0.2396P] 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         2259
_refine_ls_number_parameters     107
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0190
_refine_ls_R_factor_gt           0.0182
_refine_ls_wR_factor_ref         0.0474
_refine_ls_wR_factor_gt          0.0468
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
C1 C 1.25895(17) 0.24253(13) 0.15500(13) 0.0103(2) Uani 1 1 d . . . . .
C2 C 1.22043(17) 0.50523(13) 0.25824(13) 0.0118(2) Uani 1 1 d . . . . .
H12 H 1.3546 0.5138 0.1870 0.014 Uiso 1 1 calc R U . . .
H13 H 1.2480 0.4938 0.3654 0.014 Uiso 1 1 calc R U . . .
C3 C 1.06399(18) 0.65611(14) 0.23659(14) 0.0129(2) Uani 1 1 d . . . . .
H10 H 1.1179 0.7497 0.2633 0.015 Uiso 1 1 calc R U . . .
H11 H 1.0473 0.6732 0.1268 0.015 Uiso 1 1 calc R U . . .
C4 C 0.71641(18) 0.79622(14) 0.32301(14) 0.0151(2) Uani 1 1 d . . . . .
H4A H 0.6855 0.8152 0.2167 0.018 Uiso 1 1 calc R U . . .
H4B H 0.7873 0.8845 0.3414 0.018 Uiso 1 1 calc R U . . .
C5 C 0.51125(19) 0.80054(15) 0.43673(15) 0.0177(2) Uani 1 1 d . . . . .
H5A H 0.4374 0.7160 0.4169 0.027 Uiso 1 1 calc R U . . .
H5B H 0.4237 0.9052 0.4243 0.027 Uiso 1 1 calc R U . . .
H5C H 0.5401 0.7833 0.5424 0.027 Uiso 1 1 calc R U . . .
C6 C 0.77987(17) 0.51041(14) 0.28466(14) 0.0127(2) Uani 1 1 d . . . . .
H6 H 0.7686 0.5306 0.1740 0.015 Uiso 1 1 calc R U . . .
H7 H 0.6378 0.5034 0.3447 0.015 Uiso 1 1 calc R U . . .
C7 C 0.92373(17) 0.35285(14) 0.30818(14) 0.0129(2) Uani 1 1 d . . . . .
H8 H 0.9236 0.3270 0.4200 0.015 Uiso 1 1 calc R U . . .
H9 H 0.8712 0.2657 0.2682 0.015 Uiso 1 1 calc R U . . .
N1 N 1.13876(15) 0.36327(12) 0.22740(11) 0.01087(18) Uani 1 1 d . . . . .
N2 N 0.86024(15) 0.64345(11) 0.33428(11) 0.01104(19) Uani 1 1 d . . . . .
S1 S 1.52038(4) 0.23670(3) 0.07480(3) 0.01261(7) Uani 1 1 d . . . . .
S2 S 1.17660(4) 0.06831(3) 0.12533(3) 0.01281(7) Uani 1 1 d . . . . .
Ni1 Ni 1.5000 0.0000 0.0000 0.01046(6) Uani 1 2 d S . P . .


_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 1.3202(15) . ?
C1 S2 1.7204(11) . ?
C1 S1 1.7236(11) . ?
C2 N1 1.4702(14) . ?
C2 C3 1.5184(15) . ?
C2 H12 0.9900 . ?
C2 H13 0.9900 . ?
C3 N2 1.4626(14) . ?
C3 H10 0.9900 . ?
C3 H11 0.9900 . ?
C4 N2 1.4738(14) . ?
C4 C5 1.5170(17) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 N2 1.4638(14) . ?
C6 C7 1.5194(16) . ?
C6 H6 0.9900 . ?
C6 H7 0.9900 . ?
C7 N1 1.4698(14) . ?
C7 H8 0.9900 . ?
C7 H9 0.9900 . ?
S1 Ni1 2.2111(3) . ?
S2 Ni1 2.2103(3) . ?
Ni1 S2 2.2103(3) 2_855 ?
Ni1 S1 2.2111(3) 2_855 ?

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 S2 124.89(9) . . ?
N1 C1 S1 125.14(9) . . ?
S2 C1 S1 109.97(6) . . ?
N1 C2 C3 110.51(9) . . ?
N1 C2 H12 109.5 . . ?
C3 C2 H12 109.5 . . ?
N1 C2 H13 109.5 . . ?
C3 C2 H13 109.5 . . ?
H12 C2 H13 108.1 . . ?
N2 C3 C2 110.86(9) . . ?
N2 C3 H10 109.5 . . ?
C2 C3 H10 109.5 . . ?
N2 C3 H11 109.5 . . ?
C2 C3 H11 109.5 . . ?
H10 C3 H11 108.1 . . ?
N2 C4 C5 113.46(9) . . ?
N2 C4 H4A 108.9 . . ?
C5 C4 H4A 108.9 . . ?
N2 C4 H4B 108.9 . . ?
C5 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 C7 110.87(9) . . ?
N2 C6 H6 109.5 . . ?
C7 C6 H6 109.5 . . ?
N2 C6 H7 109.5 . . ?
C7 C6 H7 109.5 . . ?
H6 C6 H7 108.1 . . ?
N1 C7 C6 110.55(9) . . ?
N1 C7 H8 109.5 . . ?
C6 C7 H8 109.5 . . ?
N1 C7 H9 109.5 . . ?
C6 C7 H9 109.5 . . ?
H8 C7 H9 108.1 . . ?
C1 N1 C7 122.12(9) . . ?
C1 N1 C2 122.63(9) . . ?
C7 N1 C2 114.33(9) . . ?
C3 N2 C6 107.78(9) . . ?
C3 N2 C4 110.15(9) . . ?
C6 N2 C4 112.10(9) . . ?
C1 S1 Ni1 85.32(4) . . ?
C1 S2 Ni1 85.42(4) . . ?
S2 Ni1 S2 180.0 2_855 . ?
S2 Ni1 S1 100.724(11) 2_855 . ?
S2 Ni1 S1 79.275(11) . . ?
S2 Ni1 S1 79.276(11) 2_855 2_855 ?
S2 Ni1 S1 100.725(11) . 2_855 ?
S1 Ni1 S1 180.000(14) . 2_855 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 N2 56.08(12) . . . . ?
N2 C6 C7 N1 -55.86(12) . . . . ?
S2 C1 N1 C7 7.68(16) . . . . ?
S1 C1 N1 C7 -172.94(8) . . . . ?
S2 C1 N1 C2 176.01(8) . . . . ?
S1 C1 N1 C2 -4.61(16) . . . . ?
C6 C7 N1 C1 -141.29(11) . . . . ?
C6 C7 N1 C2 49.48(13) . . . . ?
C3 C2 N1 C1 141.26(11) . . . . ?
C3 C2 N1 C7 -49.58(12) . . . . ?
C2 C3 N2 C6 -62.73(12) . . . . ?
C2 C3 N2 C4 174.69(9) . . . . ?
C7 C6 N2 C3 62.60(11) . . . . ?
C7 C6 N2 C4 -176.02(9) . . . . ?
C5 C4 N2 C3 -172.38(10) . . . . ?
C5 C4 N2 C6 67.61(13) . . . . ?
N1 C1 S1 Ni1 -178.01(10) . . . . ?
S2 C1 S1 Ni1 1.44(5) . . . . ?
N1 C1 S2 Ni1 178.02(10) . . . . ?
S1 C1 S2 Ni1 -1.44(5) . . . . ?

_refine_diff_density_max         0.432
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.051


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform'
_exptl_crystal_preparation       ', Magnetic properties'
