# 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 2017

####################################################################### 
# 
# 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_m101024e1
_database_code_depnum_ccdc_archive 'CCDC 1547901'
_audit_update_record             
;
2017-05-04 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H16 N10 Ni S4'
_chemical_formula_weight         679.46

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'

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   i_-4

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

_cell_length_a                   10.256(8)
_cell_length_b                   10.256(8)
_cell_length_c                   13.160(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1384.2(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    1221
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      24.97

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             692
_exptl_absorpt_coefficient_mu    1.044
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.8850
_exptl_absorpt_correction_T_max  0.9400
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5830
_diffrn_reflns_av_R_equivalents  0.2740
_diffrn_reflns_av_sigmaI/netI    0.1433
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         24.97
_reflns_number_total             1221
_reflns_number_gt                1108
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0151P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_number_reflns         1221
_refine_ls_number_parameters     99
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0678
_refine_ls_wR_factor_ref         0.1654
_refine_ls_wR_factor_gt          0.1619
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.0000 1.0000 0.0000 0.0350(4) Uani 1 4 d S . .
S1 S 0.1424(2) 0.66032(19) 0.18361(13) 0.0493(5) Uani 1 1 d . . .
N1 N 0.0752(5) 0.8171(5) 0.0388(4) 0.0388(13) Uani 1 1 d . . .
N2 N 0.0408(6) 0.8999(6) 0.2080(4) 0.0467(14) Uani 1 1 d . . .
N3 N 0.0000 1.0000 0.1558(5) 0.0375(16) Uani 1 2 d S . .
C1 C 0.1212(6) 0.7062(6) -0.0080(6) 0.0405(14) Uani 1 1 d . . .
C2 C 0.1313(7) 0.6896(7) -0.1132(6) 0.0482(17) Uani 1 1 d . . .
H2 H 0.1033 0.7559 -0.1586 0.058 Uiso 1 1 calc R . .
C3 C 0.1829(10) 0.5742(8) -0.1491(6) 0.067(2) Uani 1 1 d . . .
H3 H 0.1908 0.5604 -0.2202 0.080 Uiso 1 1 calc R . .
C4 C 0.2242(10) 0.4764(9) -0.0804(7) 0.073(3) Uani 1 1 d . . .
H4 H 0.2590 0.3975 -0.1068 0.088 Uiso 1 1 calc R . .
C5 C 0.2159(9) 0.4912(8) 0.0222(5) 0.060(2) Uani 1 1 d . . .
H5 H 0.2448 0.4243 0.0668 0.072 Uiso 1 1 calc R . .
C6 C 0.1636(7) 0.6078(7) 0.0605(5) 0.0485(17) Uani 1 1 d . . .
C7 C 0.0788(6) 0.8063(7) 0.1359(5) 0.0428(16) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ni1 0.0318(6) 0.0318(6) 0.0414(8) 0.000 0.000 0.000
S1 0.0499(11) 0.0465(12) 0.0516(10) 0.0146(8) 0.0082(8) 0.0106(9)
N1 0.031(3) 0.042(3) 0.044(3) 0.006(2) -0.001(2) 0.004(3)
N2 0.050(4) 0.047(4) 0.043(3) 0.005(3) 0.005(2) 0.014(3)
N3 0.024(4) 0.047(5) 0.041(4) 0.000 0.000 -0.003(4)
C1 0.032(3) 0.039(4) 0.050(3) -0.001(3) -0.002(3) -0.003(2)
C2 0.046(4) 0.044(4) 0.054(4) -0.010(3) -0.006(3) 0.002(3)
C3 0.080(6) 0.052(5) 0.069(5) -0.023(4) -0.007(4) 0.015(4)
C4 0.088(7) 0.052(5) 0.079(6) -0.006(5) -0.003(6) 0.031(4)
C5 0.066(5) 0.047(5) 0.067(6) 0.001(4) -0.002(4) 0.016(4)
C6 0.044(4) 0.044(4) 0.057(4) 0.001(3) 0.002(3) 0.001(3)
C7 0.029(3) 0.049(4) 0.051(4) 0.007(3) 0.002(3) -0.001(3)

_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 N3 2.051(6) 2_465 ?
Ni1 N3 2.051(6) . ?
Ni1 N1 2.092(6) 2_465 ?
Ni1 N1 2.092(6) 4_665 ?
Ni1 N1 2.092(6) . ?
Ni1 N1 2.092(6) 3_575 ?
S1 C6 1.721(7) . ?
S1 C7 1.750(7) . ?
N1 C7 1.284(8) . ?
N1 C1 1.377(8) . ?
N2 N3 1.305(6) . ?
N2 C7 1.404(9) . ?
N3 N2 1.305(6) 3_575 ?
C1 C2 1.398(10) . ?
C1 C6 1.422(10) . ?
C2 C3 1.380(10) . ?
C2 H2 0.9500 . ?
C3 C4 1.416(11) . ?
C3 H3 0.9500 . ?
C4 C5 1.361(12) . ?
C4 H4 0.9500 . ?
C5 C6 1.404(10) . ?
C5 H5 0.9500 . ?

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
N3 Ni1 N3 180.000(1) 2_465 . ?
N3 Ni1 N1 75.87(14) 2_465 2_465 ?
N3 Ni1 N1 104.13(14) . 2_465 ?
N3 Ni1 N1 75.87(14) 2_465 4_665 ?
N3 Ni1 N1 104.13(14) . 4_665 ?
N1 Ni1 N1 151.7(3) 2_465 4_665 ?
N3 Ni1 N1 104.13(14) 2_465 . ?
N3 Ni1 N1 75.87(14) . . ?
N1 Ni1 N1 93.42(7) 2_465 . ?
N1 Ni1 N1 93.42(7) 4_665 . ?
N3 Ni1 N1 104.13(14) 2_465 3_575 ?
N3 Ni1 N1 75.87(14) . 3_575 ?
N1 Ni1 N1 93.42(7) 2_465 3_575 ?
N1 Ni1 N1 93.42(7) 4_665 3_575 ?
N1 Ni1 N1 151.7(3) . 3_575 ?
C6 S1 C7 88.7(3) . . ?
C7 N1 C1 111.4(6) . . ?
C7 N1 Ni1 109.3(5) . . ?
C1 N1 Ni1 139.3(4) . . ?
N3 N2 C7 105.7(5) . . ?
N2 N3 N2 116.5(6) . 3_575 ?
N2 N3 Ni1 121.8(3) . . ?
N2 N3 Ni1 121.8(3) 3_575 . ?
N1 C1 C2 124.7(6) . . ?
N1 C1 C6 114.0(6) . . ?
C2 C1 C6 121.3(7) . . ?
C3 C2 C1 118.2(7) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 120.2(7) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 122.4(7) . . ?
C5 C4 H4 118.8 . . ?
C3 C4 H4 118.8 . . ?
C4 C5 C6 118.4(7) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C5 C6 C1 119.6(7) . . ?
C5 C6 S1 130.8(6) . . ?
C1 C6 S1 109.6(5) . . ?
N1 C7 N2 127.3(7) . . ?
N1 C7 S1 116.2(5) . . ?
N2 C7 S1 116.5(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 Ni1 N1 C7 -179.7(4) 2_465 . . . ?
N3 Ni1 N1 C7 0.3(4) . . . . ?
N1 Ni1 N1 C7 -103.4(4) 2_465 . . . ?
N1 Ni1 N1 C7 104.1(4) 4_665 . . . ?
N1 Ni1 N1 C7 0.3(4) 3_575 . . . ?
N3 Ni1 N1 C1 0.3(7) 2_465 . . . ?
N3 Ni1 N1 C1 -179.7(7) . . . . ?
N1 Ni1 N1 C1 76.5(7) 2_465 . . . ?
N1 Ni1 N1 C1 -76.0(7) 4_665 . . . ?
N1 Ni1 N1 C1 -179.7(7) 3_575 . . . ?
C7 N2 N3 N2 179.9(6) . . . 3_575 ?
C7 N2 N3 Ni1 -0.1(6) . . . . ?
N3 Ni1 N3 N2 0(100) 2_465 . . . ?
N1 Ni1 N3 N2 89.8(4) 2_465 . . . ?
N1 Ni1 N3 N2 -90.2(4) 4_665 . . . ?
N1 Ni1 N3 N2 -0.2(4) . . . . ?
N1 Ni1 N3 N2 179.8(4) 3_575 . . . ?
N3 Ni1 N3 N2 0(100) 2_465 . . 3_575 ?
N1 Ni1 N3 N2 -90.2(4) 2_465 . . 3_575 ?
N1 Ni1 N3 N2 89.8(4) 4_665 . . 3_575 ?
N1 Ni1 N3 N2 179.8(4) . . . 3_575 ?
N1 Ni1 N3 N2 -0.2(4) 3_575 . . 3_575 ?
C7 N1 C1 C2 -178.9(6) . . . . ?
Ni1 N1 C1 C2 1.2(11) . . . . ?
C7 N1 C1 C6 -1.1(8) . . . . ?
Ni1 N1 C1 C6 179.0(5) . . . . ?
N1 C1 C2 C3 178.1(7) . . . . ?
C6 C1 C2 C3 0.5(12) . . . . ?
C1 C2 C3 C4 -0.1(14) . . . . ?
C2 C3 C4 C5 -0.4(16) . . . . ?
C3 C4 C5 C6 0.4(15) . . . . ?
C4 C5 C6 C1 0.0(12) . . . . ?
C4 C5 C6 S1 -178.3(7) . . . . ?
N1 C1 C6 C5 -178.3(7) . . . . ?
C2 C1 C6 C5 -0.5(11) . . . . ?
N1 C1 C6 S1 0.3(8) . . . . ?
C2 C1 C6 S1 178.2(6) . . . . ?
C7 S1 C6 C5 178.8(8) . . . . ?
C7 S1 C6 C1 0.3(5) . . . . ?
C1 N1 C7 N2 179.5(7) . . . . ?
Ni1 N1 C7 N2 -0.6(9) . . . . ?
C1 N1 C7 S1 1.3(8) . . . . ?
Ni1 N1 C7 S1 -178.7(3) . . . . ?
N3 N2 C7 N1 0.5(9) . . . . ?
N3 N2 C7 S1 178.6(4) . . . . ?
C6 S1 C7 N1 -1.0(6) . . . . ?
C6 S1 C7 N2 -179.3(6) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.97
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.365
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.093
