# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 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_1224jkb1
_database_code_depnum_ccdc_archive 'CCDC 1581238'
_audit_update_record             
;
2017-10-21 deposited with the CCDC.
2018-01-11 downloaded from the CCDC.
;

_audit_creation_date             2017-10-21T16:15:49-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H22 N6  S2'
_chemical_formula_sum            'C13 H22 N6  S2'
_chemical_formula_weight         326.49
_chemical_compound_source        'synthesis as described'

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

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

_cell_length_a                   10.0053(2)
_cell_length_b                   17.3101(3)
_cell_length_c                   10.1355(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.384(2)
_cell_angle_gamma                90
_cell_volume                     1720.86(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    4325
_cell_measurement_theta_min      5.13
_cell_measurement_theta_max      62.444
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.26
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.313
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
        (compiled Jan 14 2014,18:38:05)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.79583
_exptl_absorpt_correction_T_max  1

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

_diffrn_source                   'sealed X-ray tube'
_diffrn_ambient_temperature      190(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 16.0696
_diffrn_orient_matrix_ub_11      -0.0931309
_diffrn_orient_matrix_ub_12      0.0681297
_diffrn_orient_matrix_ub_13      0.0199942
_diffrn_orient_matrix_ub_21      0.0840079
_diffrn_orient_matrix_ub_22      0.0125376
_diffrn_orient_matrix_ub_23      0.1429596
_diffrn_orient_matrix_ub_31      0.0944979
_diffrn_orient_matrix_ub_32      0.0559259
_diffrn_orient_matrix_ub_33      -0.0565159
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_number            6942
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         24.11
_diffrn_reflns_theta_full        24.11
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_reflns_number_total             2722
_reflns_number_gt                2492
_reflns_threshold_expression     >2σ(I)

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

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
        (compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
        (compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
        (compiled Jan 14 2014,18:38:05)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_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 > 2σ(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)+(0.0513P)²+0.2481P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.077(3)
_refine_ls_number_reflns         2722
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.034
_refine_ls_wR_factor_ref         0.0897
_refine_ls_wR_factor_gt          0.0858
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.047

#----------------------------------------------------------------------------#
#                   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'
O O 0.0106 0.006 '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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.72527(18) 0.61182(11) 0.4856(2) 0.0454(4) Uani 1 1 d . . .
H1A H 0.775 0.634 0.5701 0.068 Uiso 1 1 calc R . .
H1B H 0.672 0.5673 0.5053 0.068 Uiso 1 1 calc R . .
H1C H 0.6639 0.6508 0.4365 0.068 Uiso 1 1 calc R . .
C2 C 0.82340(16) 0.58669(9) 0.40262(16) 0.0322(4) Uani 1 1 d . . .
C3 C 0.78214(17) 0.55056(10) 0.26684(17) 0.0388(4) Uani 1 1 d . . .
H3A H 0.7109 0.5816 0.2084 0.047 Uiso 1 1 calc R . .
H3B H 0.7475 0.4974 0.2738 0.047 Uiso 1 1 calc R . .
C4 C 0.91372(16) 0.55003(9) 0.21293(15) 0.0326(4) Uani 1 1 d . . .
C5 C 0.92198(19) 0.61777(10) 0.11915(17) 0.0426(4) Uani 1 1 d . . .
H5A H 0.9084 0.6662 0.1649 0.064 Uiso 1 1 calc R . .
H5B H 0.8511 0.6124 0.0378 0.064 Uiso 1 1 calc R . .
H5C H 1.0118 0.6183 0.0943 0.064 Uiso 1 1 calc R . .
C6 C 1.15273(15) 0.57289(8) 0.35432(15) 0.0293(3) Uani 1 1 d . . .
C7 C 1.35615(17) 0.63568(12) 0.4871(2) 0.0496(5) Uani 1 1 d . . .
H7A H 1.41 0.5943 0.4548 0.06 Uiso 1 1 calc R . .
H7B H 1.389 0.6409 0.5854 0.06 Uiso 1 1 calc R . .
C8 C 1.3806(2) 0.71007(13) 0.4204(3) 0.0622(7) Uani 1 1 d . . .
H8 H 1.4709 0.7299 0.4407 0.075 Uiso 1 1 calc R . .
C9 C 1.2926(3) 0.75024(14) 0.3383(3) 0.0703(7) Uani 1 1 d . . .
H9A H 1.2007 0.7332 0.3144 0.084 Uiso 1 1 calc R . .
H9B H 1.3196 0.7969 0.3017 0.084 Uiso 1 1 calc R . .
C10 C 0.83184(16) 0.35780(9) 0.17753(15) 0.0308(4) Uani 1 1 d . . .
C11 C 0.63359(18) 0.32162(10) 0.00192(17) 0.0412(4) Uani 1 1 d . . .
H11A H 0.6539 0.2677 0.0317 0.049 Uiso 1 1 calc R . .
H11B H 0.6219 0.3226 -0.0974 0.049 Uiso 1 1 calc R . .
C12 C 0.5033(2) 0.34525(13) 0.0392(2) 0.0558(5) Uani 1 1 d . . .
H12 H 0.4276 0.3121 0.0096 0.067 Uiso 1 1 calc R . .
C13 C 0.4803(3) 0.40479(18) 0.1063(3) 0.0904(10) Uani 1 1 d . . .
H13A H 0.5519 0.4401 0.1387 0.108 Uiso 1 1 calc R . .
H13B H 0.3917 0.4136 0.1237 0.108 Uiso 1 1 calc R . .
N1 N 0.95290(13) 0.59176(7) 0.44381(13) 0.0301(3) Uani 1 1 d . . .
N2 N 1.01675(13) 0.56071(7) 0.34312(12) 0.0286(3) Uani 1 1 d . . .
N3 N 1.21354(13) 0.61309(8) 0.46129(14) 0.0361(3) Uani 1 1 d . . .
H3 H 1.1642 0.6269 0.5202 0.043 Uiso 1 1 calc R . .
N4 N 0.93394(16) 0.47908(8) 0.14236(13) 0.0369(3) Uani 1 1 d . . .
H4A H 1.0177 0.4812 0.118 0.044 Uiso 1 1 d R . .
N5 N 0.92812(15) 0.41182(8) 0.21932(13) 0.0369(3) Uani 1 1 d . . .
H5 H 0.9875 0.405 0.2949 0.044 Uiso 1 1 calc R . .
N6 N 0.74989(14) 0.36994(8) 0.05932(13) 0.0371(3) Uani 1 1 d . . .
H6 H 0.7671 0.4101 0.0122 0.044 Uiso 1 1 calc R . .
S1 S 1.24018(4) 0.53414(2) 0.24260(4) 0.03726(18) Uani 1 1 d . . .
S2 S 0.82385(5) 0.27970(2) 0.27539(4) 0.03836(18) Uani 1 1 d . . .



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

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 1.479(2) . ?
C2 N1 1.283(2) . ?
C2 C3 1.494(2) . ?
C3 C4 1.522(2) . ?
C4 N4 1.455(2) . ?
C4 N2 1.5170(19) . ?
C4 C5 1.522(2) . ?
C6 N3 1.330(2) . ?
C6 N2 1.359(2) . ?
C6 S1 1.6996(15) . ?
C7 N3 1.453(2) . ?
C7 C8 1.497(3) . ?
C8 C9 1.289(4) . ?
C10 N6 1.328(2) . ?
C10 N5 1.349(2) . ?
C10 S2 1.6880(16) . ?
C11 N6 1.458(2) . ?
C11 C12 1.485(3) . ?
C12 C13 1.281(3) . ?
N1 N2 1.4127(18) . ?
N4 N5 1.4090(19) . ?

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 C2 C1 122.40(16) . . ?
N1 C2 C3 113.95(14) . . ?
C1 C2 C3 123.61(15) . . ?
C2 C3 C4 103.42(13) . . ?
N4 C4 N2 113.19(13) . . ?
N4 C4 C3 113.31(13) . . ?
N2 C4 C3 100.05(12) . . ?
N4 C4 C5 108.26(13) . . ?
N2 C4 C5 109.76(12) . . ?
C3 C4 C5 112.15(14) . . ?
N3 C6 N2 116.01(13) . . ?
N3 C6 S1 122.46(12) . . ?
N2 C6 S1 121.44(11) . . ?
N3 C7 C8 113.12(17) . . ?
C9 C8 C7 127.1(2) . . ?
N6 C10 N5 116.67(14) . . ?
N6 C10 S2 124.36(12) . . ?
N5 C10 S2 118.97(12) . . ?
N6 C11 C12 114.35(15) . . ?
C13 C12 C11 128.0(2) . . ?
C2 N1 N2 108.09(13) . . ?
C6 N2 N1 117.94(12) . . ?
C6 N2 C4 126.06(12) . . ?
N1 N2 C4 110.38(12) . . ?
C6 N3 C7 124.24(14) . . ?
N5 N4 C4 113.60(12) . . ?
C10 N5 N4 120.26(13) . . ?
C10 N6 C11 124.84(14) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3 S2 0.88 2.61 3.3319(14) 139.7 3_766
N4 H4A S1 0.92 2.51 3.1780(15) 130.2 .
N5 H5 N1 0.88 2.6 3.3874(18) 149.8 3_766
N6 H6 N4 0.88 2.25 2.6566(19) 107.6 .
N3 H3 N1 0.88 2.19 2.6050(18) 108.5 .

# 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_1710jb10
_database_code_depnum_ccdc_archive 'CCDC 1581239'
_audit_update_record             
;
2017-10-21 deposited with the CCDC.
2018-01-11 downloaded from the CCDC.
;

_audit_creation_date             2017-10-21T16:08:04-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H18 N6 Ni1 O1 S2,C3 H7 N O'
_chemical_formula_sum            'C22 H25 N7 Ni O2 S2'
_chemical_formula_weight         542.32
_chemical_compound_source        'synthesis as described'

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

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
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'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.8455(9)
_cell_length_b                   7.4159(6)
_cell_length_c                   36.322(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.341(5)
_cell_angle_gamma                90
_cell_volume                     4802.9(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    2866
_cell_measurement_theta_min      4.888
_cell_measurement_theta_max      62.25
_cell_measurement_wavelength     1.54184

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

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear black'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.5
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2256
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    3.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.47612
_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  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0696
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.0400235
_diffrn_orient_matrix_ub_12      -0.0182462
_diffrn_orient_matrix_ub_13      0.0382062
_diffrn_orient_matrix_ub_21      -0.0634642
_diffrn_orient_matrix_ub_22      0.107725
_diffrn_orient_matrix_ub_23      0.0172618
_diffrn_orient_matrix_ub_31      -0.0429199
_diffrn_orient_matrix_ub_32      -0.176651
_diffrn_orient_matrix_ub_33      0.0065712
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0831
_diffrn_reflns_av_unetI/netI     0.0604
_diffrn_reflns_number            16766
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         4.87
_diffrn_reflns_theta_max         62.46
_diffrn_reflns_theta_full        62.46
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_reflns_number_total             3807
_reflns_number_gt                2843
_reflns_threshold_expression     >2σ(I)

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

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_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 > 2σ(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)+(0.1061P)²+17.1120P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3807
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0973
_refine_ls_R_factor_gt           0.0744
_refine_ls_wR_factor_ref         0.2127
_refine_ls_wR_factor_gt          0.193
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.792
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.096

#----------------------------------------------------------------------------#
#                   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'
O O 0.0492 0.0322 '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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0723(4) 0.3144(9) -0.06281(16) 0.0525(15) Uani 1 1 d . . .
H1A H 1.0253 0.2774 -0.0755 0.079 Uiso 1 1 calc R . .
H1B H 1.1128 0.2336 -0.0698 0.079 Uiso 1 1 calc R . .
H1C H 1.0844 0.4383 -0.0698 0.079 Uiso 1 1 calc R . .
C2 C 1.0639(3) 0.3052(8) -0.02205(16) 0.0437(13) Uani 1 1 d . . .
C3 C 1.1295(3) 0.3571(8) 0.00170(17) 0.0479(14) Uani 1 1 d . . .
C4 C 1.1354(3) 0.3460(8) 0.04285(16) 0.0470(13) Uani 1 1 d . . .
C5 C 1.2087(3) 0.3871(10) 0.06180(18) 0.0604(17) Uani 1 1 d . . .
H5A H 1.2042 0.3745 0.0885 0.091 Uiso 1 1 calc R . .
H5B H 1.2234 0.5109 0.056 0.091 Uiso 1 1 calc R . .
H5C H 1.2467 0.303 0.0534 0.091 Uiso 1 1 calc R . .
C6 C 0.8844(3) 0.1592(7) -0.02099(15) 0.0416(12) Uani 1 1 d . . .
C7 C 1.0356(3) 0.2576(8) 0.11804(16) 0.0459(13) Uani 1 1 d . . .
C8 C 1.1067(4) 0.2888(9) 0.17876(17) 0.0545(15) Uani 1 1 d . . .
C9 C 1.1707(4) 0.3795(12) 0.1679(2) 0.072(2) Uani 1 1 d . . .
H9 H 1.1732 0.4239 0.1435 0.086 Uiso 1 1 calc R . .
C10 C 1.2302(5) 0.4046(14) 0.1927(2) 0.084(2) Uani 1 1 d . . .
H10 H 1.2736 0.4661 0.185 0.1 Uiso 1 1 calc R . .
C11 C 1.2283(5) 0.3434(13) 0.2279(2) 0.079(2) Uani 1 1 d . . .
H11 H 1.2699 0.3617 0.2447 0.095 Uiso 1 1 calc R . .
C12 C 1.1655(4) 0.2547(11) 0.2391(2) 0.0686(19) Uani 1 1 d . . .
H12 H 1.1638 0.2111 0.2637 0.082 Uiso 1 1 calc R . .
C13 C 1.1051(4) 0.2289(10) 0.21483(18) 0.0588(16) Uani 1 1 d . . .
H13 H 1.0616 0.1692 0.223 0.071 Uiso 1 1 calc R . .
C14 C 0.8152(3) 0.1283(9) -0.08247(16) 0.0490(14) Uani 1 1 d . . .
C15 C 0.8755(3) 0.1344(10) -0.10582(17) 0.0566(16) Uani 1 1 d . . .
H15 H 0.9257 0.1331 -0.096 0.068 Uiso 1 1 calc R . .
C16 C 0.8607(4) 0.1426(11) -0.14341(18) 0.0653(18) Uani 1 1 d . . .
H16 H 0.9014 0.1467 -0.1595 0.078 Uiso 1 1 calc R . .
C17 C 0.7891(4) 0.1449(13) -0.15797(19) 0.074(2) Uani 1 1 d . . .
H17 H 0.7798 0.1505 -0.1839 0.088 Uiso 1 1 calc R . .
C18 C 0.7297(4) 0.1388(12) -0.13431(19) 0.071(2) Uani 1 1 d . . .
H18 H 0.6794 0.1413 -0.144 0.085 Uiso 1 1 calc R . .
C19 C 0.7440(3) 0.1292(10) -0.09730(18) 0.0586(16) Uani 1 1 d . . .
H19 H 0.7032 0.123 -0.0814 0.07 Uiso 1 1 calc R . .
N1 N 1.0014(2) 0.2550(6) -0.00822(12) 0.0393(10) Uani 1 1 d . . .
N2 N 0.9464(3) 0.2147(7) -0.03462(13) 0.0453(11) Uani 1 1 d . . .
N3 N 0.8246(3) 0.1155(7) -0.04347(12) 0.0474(11) Uani 1 1 d . . .
H3 H 0.7857 0.0727 -0.0322 0.057 Uiso 1 1 calc R . .
N4 N 1.0770(3) 0.3050(6) 0.06150(12) 0.0428(11) Uani 1 1 d . . .
N5 N 1.0919(3) 0.3137(7) 0.09879(13) 0.0524(12) Uani 1 1 d . . .
N6 N 1.0430(3) 0.2528(8) 0.15563(13) 0.0541(13) Uani 1 1 d . . .
H6 H 1.0023 0.2231 0.167 0.065 Uiso 1 1 calc R . .
O1 O 1.1850(2) 0.4151(6) -0.01344(12) 0.0579(11) Uani 1 1 d . . .
S1 S 0.87131(8) 0.1322(2) 0.02604(4) 0.0483(4) Uani 1 1 d . . .
S2 S 0.95048(8) 0.1868(2) 0.09889(4) 0.0499(4) Uani 1 1 d . . .
Ni1 Ni 0.98131(5) 0.22498(13) 0.04278(2) 0.0432(3) Uani 1 1 d . . .
C20 C 0.9284(5) -0.1021(16) 0.2111(3) 0.092(3) Uani 1 1 d . . .
H20 H 0.9249 -0.1032 0.2371 0.11 Uiso 1 1 calc R . .
C21 C 0.9257(8) -0.2661(18) 0.1548(3) 0.129(4) Uani 1 1 d . . .
H21A H 0.921 -0.392 0.1468 0.194 Uiso 1 1 calc R . .
H21B H 0.9735 -0.2171 0.1469 0.194 Uiso 1 1 calc R . .
H21C H 0.8843 -0.1954 0.1436 0.194 Uiso 1 1 calc R . .
C22 C 0.9086(8) -0.4236(17) 0.2131(3) 0.132(4) Uani 1 1 d . . .
H22A H 0.9074 -0.5223 0.1951 0.199 Uiso 1 1 calc R . .
H22B H 0.86 -0.4161 0.2247 0.199 Uiso 1 1 calc R . .
H22C H 0.9482 -0.4463 0.232 0.199 Uiso 1 1 calc R . .
N7 N 0.9233(4) -0.2571(10) 0.19474(18) 0.0806(19) Uani 1 1 d . . .
O2 O 0.9372(3) 0.0476(8) 0.19674(15) 0.0813(16) Uani 1 1 d . . .



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

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 1.496(8) . ?
C2 N1 1.296(7) . ?
C2 C3 1.477(9) . ?
C3 O1 1.229(7) . ?
C3 C4 1.497(9) . ?
C4 N4 1.301(7) . ?
C4 C5 1.484(9) . ?
C6 N2 1.298(7) . ?
C6 N3 1.356(7) . ?
C6 S1 1.745(6) . ?
C7 N5 1.316(8) . ?
C7 N6 1.367(8) . ?
C7 S2 1.726(6) . ?
C8 C13 1.385(9) . ?
C8 C9 1.395(10) . ?
C8 N6 1.411(8) . ?
C9 C10 1.376(11) . ?
C10 C11 1.361(11) . ?
C11 C12 1.374(11) . ?
C12 C13 1.379(10) . ?
C14 C19 1.359(9) . ?
C14 C15 1.398(8) . ?
C14 N3 1.423(7) . ?
C15 C16 1.381(9) . ?
C16 C17 1.364(10) . ?
C17 C18 1.392(10) . ?
C18 C19 1.360(10) . ?
N1 N2 1.376(7) . ?
N1 Ni1 1.914(4) . ?
N4 N5 1.371(7) . ?
N4 Ni1 1.908(5) . ?
S1 Ni1 2.1443(17) . ?
S2 Ni1 2.1512(16) . ?
C20 O2 1.238(12) . ?
C20 N7 1.295(12) . ?
C21 N7 1.456(11) . ?
C22 N7 1.432(13) . ?

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 C2 C3 121.5(5) . . ?
N1 C2 C1 121.3(5) . . ?
C3 C2 C1 117.2(5) . . ?
O1 C3 C2 117.6(5) . . ?
O1 C3 C4 116.2(5) . . ?
C2 C3 C4 126.2(5) . . ?
N4 C4 C5 121.0(5) . . ?
N4 C4 C3 120.6(5) . . ?
C5 C4 C3 118.4(5) . . ?
N2 C6 N3 120.6(5) . . ?
N2 C6 S1 124.1(4) . . ?
N3 C6 S1 115.4(4) . . ?
N5 C7 N6 119.6(5) . . ?
N5 C7 S2 124.1(5) . . ?
N6 C7 S2 116.3(4) . . ?
C13 C8 C9 118.1(6) . . ?
C13 C8 N6 117.1(6) . . ?
C9 C8 N6 124.9(6) . . ?
C10 C9 C8 120.0(7) . . ?
C11 C10 C9 121.4(7) . . ?
C10 C11 C12 119.4(7) . . ?
C11 C12 C13 120.2(7) . . ?
C12 C13 C8 121.0(6) . . ?
C19 C14 C15 119.3(6) . . ?
C19 C14 N3 117.7(5) . . ?
C15 C14 N3 122.9(5) . . ?
C16 C15 C14 118.7(6) . . ?
C17 C16 C15 121.5(6) . . ?
C16 C17 C18 119.0(6) . . ?
C19 C18 C17 119.7(6) . . ?
C14 C19 C18 121.8(6) . . ?
C2 N1 N2 113.1(4) . . ?
C2 N1 Ni1 127.4(4) . . ?
N2 N1 Ni1 119.5(3) . . ?
C6 N2 N1 113.4(4) . . ?
C6 N3 C14 129.9(5) . . ?
C4 N4 N5 112.1(5) . . ?
C4 N4 Ni1 127.7(4) . . ?
N5 N4 Ni1 120.1(3) . . ?
C7 N5 N4 112.9(5) . . ?
C7 N6 C8 129.3(5) . . ?
C6 S1 Ni1 94.77(19) . . ?
C7 S2 Ni1 95.0(2) . . ?
N4 Ni1 N1 96.22(19) . . ?
N4 Ni1 S1 175.58(14) . . ?
N1 Ni1 S1 88.20(14) . . ?
N4 Ni1 S2 87.88(14) . . ?
N1 Ni1 S2 175.87(14) . . ?
S1 Ni1 S2 87.70(6) . . ?
O2 C20 N7 127.6(9) . . ?
C20 N7 C22 124.3(9) . . ?
C20 N7 C21 119.5(9) . . ?
C22 N7 C21 116.0(9) . . ?

# END of CIF
