# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_cw1246a
_database_code_depnum_ccdc_archive 'CCDC 1980434'
loop_
_audit_author_name
_audit_author_address
'Christian Naether'
;Kiel University
Germany
;
_audit_update_record             
;
2020-01-28 deposited with the CCDC.	2020-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H22 N4 Ni O2 S2'
_chemical_formula_weight         425.20

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.1142(5)
_cell_length_b                   14.0364(6)
_cell_length_c                   7.8828(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.883(4)
_cell_angle_gamma                90
_cell_volume                     990.31(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    7715
_cell_measurement_theta_min      2.275
_cell_measurement_theta_max      26.005

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_F_000             444
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1252
_exptl_crystal_size_mid          0.0916
_exptl_crystal_size_min          0.0617
_exptl_absorpt_coefficient_mu    1.207
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_min  0.7989
_exptl_absorpt_correction_T_max  0.9148
_exptl_absorpt_process_details   'X-Shape and X-Red 32 (STOE, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'STOE IPDS-2'
_diffrn_measurement_method       'Omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7715
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_av_R_equivalents  0.1104
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.275
_diffrn_reflns_theta_max         26.005
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1945
_reflns_number_gt                1719
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_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)+(0.1189P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.026(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1945
_refine_ls_number_parameters     117
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0583
_refine_ls_wR_factor_ref         0.1566
_refine_ls_wR_factor_gt          0.1526
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_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
Ni1 Ni 0.500000 0.500000 0.500000 0.0399(3) Uani 1 2 d S . P . .
N1 N 0.5822(3) 0.42908(17) 0.7247(3) 0.0480(6) Uani 1 1 d . . . . .
C1 C 0.6305(3) 0.38307(18) 0.8423(3) 0.0395(6) Uani 1 1 d . . . . .
S1 S 0.70218(9) 0.31697(5) 1.01059(9) 0.0480(3) Uani 1 1 d . . . . .
N11 N 0.3107(3) 0.41151(17) 0.4616(3) 0.0445(6) Uani 1 1 d . . . . .
C11 C 0.3237(3) 0.31695(19) 0.4871(4) 0.0462(7) Uani 1 1 d . . . . .
H11 H 0.420768 0.291893 0.527987 0.055 Uiso 1 1 calc R U . . .
C12 C 0.2067(3) 0.2545(2) 0.4583(4) 0.0491(7) Uani 1 1 d . . . . .
C13 C 0.0647(3) 0.2921(2) 0.4011(5) 0.0571(8) Uani 1 1 d . . . . .
H13 H -0.020269 0.251565 0.380486 0.069 Uiso 1 1 calc R U . . .
C14 C 0.0489(3) 0.3892(2) 0.3746(5) 0.0578(8) Uani 1 1 d . . . . .
H14 H -0.046994 0.416264 0.335145 0.069 Uiso 1 1 calc R U . . .
C15 C 0.1732(3) 0.4459(2) 0.4060(4) 0.0487(7) Uani 1 1 d . . . . .
H15 H 0.161336 0.512537 0.387471 0.058 Uiso 1 1 calc R U . . .
C16 C 0.2376(4) 0.1490(2) 0.4887(5) 0.0660(10) Uani 1 1 d . . . . .
H16A H 0.336397 0.134623 0.459835 0.079 Uiso 1 1 calc R U . . .
H16B H 0.244859 0.135984 0.613460 0.079 Uiso 1 1 calc R U . . .
C17 C 0.1286(7) 0.0834(3) 0.3924(7) 0.0992(18) Uani 1 1 d . . . . .
H17A H 0.034112 0.088780 0.433898 0.149 Uiso 1 1 calc R U . . .
H17B H 0.166225 0.018034 0.409397 0.149 Uiso 1 1 calc R U . . .
H17C H 0.112149 0.099366 0.269249 0.149 Uiso 1 1 calc R U . . .
O1 O 0.6183(3) 0.40322(14) 0.3707(3) 0.0515(5) Uani 1 1 d . . . . .
H1A H 0.612980 0.402444 0.263161 0.077 Uiso 1 1 d R U . . .
H2A H 0.627133 0.347324 0.409331 0.077 Uiso 1 1 d R U . . .


_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 N1 2.047(3) 3_666 ?
Ni1 N1 2.047(3) . ?
Ni1 N11 2.101(2) . ?
Ni1 N11 2.101(2) 3_666 ?
Ni1 O1 2.112(2) . ?
Ni1 O1 2.112(2) 3_666 ?
N1 C1 1.147(4) . ?
C1 S1 1.649(3) . ?
N11 C15 1.337(4) . ?
N11 C11 1.344(4) . ?
C11 C12 1.367(4) . ?
C12 C13 1.391(4) . ?
C12 C16 1.518(4) . ?
C13 C14 1.383(4) . ?
C14 C15 1.368(4) . ?
C16 C17 1.458(5) . ?

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 Ni1 N1 180.0 3_666 . ?
N1 Ni1 N11 90.36(10) 3_666 . ?
N1 Ni1 N11 89.64(10) . . ?
N1 Ni1 N11 89.64(10) 3_666 3_666 ?
N1 Ni1 N11 90.36(10) . 3_666 ?
N11 Ni1 N11 180.0 . 3_666 ?
N1 Ni1 O1 91.83(9) 3_666 . ?
N1 Ni1 O1 88.17(9) . . ?
N11 Ni1 O1 91.73(9) . . ?
N11 Ni1 O1 88.27(9) 3_666 . ?
N1 Ni1 O1 88.17(9) 3_666 3_666 ?
N1 Ni1 O1 91.83(9) . 3_666 ?
N11 Ni1 O1 88.27(9) . 3_666 ?
N11 Ni1 O1 91.73(9) 3_666 3_666 ?
O1 Ni1 O1 180.0 . 3_666 ?
C1 N1 Ni1 174.3(2) . . ?
N1 C1 S1 179.3(3) . . ?
C15 N11 C11 117.1(2) . . ?
C15 N11 Ni1 121.82(19) . . ?
C11 N11 Ni1 121.02(18) . . ?
N11 C11 C12 124.4(2) . . ?
C11 C12 C13 117.3(3) . . ?
C11 C12 C16 118.9(3) . . ?
C13 C12 C16 123.7(3) . . ?
C14 C13 C12 119.2(3) . . ?
C15 C14 C13 119.1(3) . . ?
N11 C15 C14 122.8(3) . . ?
C17 C16 C12 116.4(3) . . ?

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
_geom_hbond_publ_flag
C11 H11 S1 0.95 3.01 3.902(3) 156.8 4_565 yes
O1 H1A S1 0.84 2.58 3.306(2) 144.8 1_554 yes
O1 H2A S1 0.84 2.49 3.322(2) 169.0 4_565 yes

_refine_diff_density_max         0.984
_refine_diff_density_min         -0.828
_refine_diff_density_rms         0.123

####################################################################### 
# 
# 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_cw1829
_database_code_depnum_ccdc_archive 'CCDC 1980435'
loop_
_audit_author_name
_audit_author_address
'Christian Naether'
;Kiel University
Germany
;
_audit_update_record             
;
2020-01-28 deposited with the CCDC.	2020-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H20 Cl2 N4 Ni S2'
_chemical_formula_weight         474.10

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+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                   16.8134(6)
_cell_length_b                   14.9609(3)
_cell_length_c                   9.801
_cell_angle_alpha                90
_cell_angle_beta                 114.894(2)
_cell_angle_gamma                90
_cell_volume                     2236.36(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    10318
_cell_measurement_theta_min      1.907
_cell_measurement_theta_max      25.999

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    1.301
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.5825
_exptl_absorpt_correction_T_max  0.7606
_exptl_absorpt_process_details   'X-Shape and X-Red 32 (STOE, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'STOE IPDS-2'
_diffrn_measurement_method       'Omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10318
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.907
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2193
_reflns_number_gt                1967
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'X-Area (STOE, 2008)'
_computing_cell_refinement       'X-Area (STOE, 2008)'
_computing_data_reduction        'X-Area (STOE, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_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)+(0.0388P)²+0.8607P] 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         2193
_refine_ls_number_parameters     116
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0251
_refine_ls_wR_factor_ref         0.0658
_refine_ls_wR_factor_gt          0.0642
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.000
_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
Ni1 Ni 0.500000 0.08865(2) 0.750000 0.02604(9) Uani 1 2 d S T P . .
S1 S 0.38778(3) 0.03511(3) 0.22107(5) 0.03649(12) Uani 1 1 d . . . . .
C1 C 0.42085(10) 0.06494(10) 0.39790(18) 0.0274(3) Uani 1 1 d . . . . .
N1 N 0.44451(9) 0.08426(9) 0.52264(16) 0.0317(3) Uani 1 1 d . . . . .
N11 N 0.58938(9) 0.18449(9) 0.74745(16) 0.0323(3) Uani 1 1 d . . . . .
C11 C 0.61217(11) 0.25347(12) 0.8426(2) 0.0371(4) Uani 1 1 d . . . . .
H11 H 0.585796 0.258528 0.910975 0.044 Uiso 1 1 calc R U . . .
C12 C 0.67240(13) 0.31835(14) 0.8470(2) 0.0507(5) Uani 1 1 d . . . . .
C13 C 0.70975(15) 0.30815(18) 0.7456(3) 0.0684(7) Uani 1 1 d . . . . .
H13 H 0.751082 0.350754 0.743344 0.082 Uiso 1 1 calc R U . . .
C14 C 0.68720(16) 0.23687(19) 0.6488(3) 0.0662(7) Uani 1 1 d . . . . .
H14 H 0.713257 0.229492 0.580339 0.079 Uiso 1 1 calc R U . . .
C15 C 0.62718(13) 0.17671(14) 0.6517(2) 0.0455(4) Uani 1 1 d . . . . .
H15 H 0.611556 0.127713 0.583727 0.055 Uiso 1 1 calc R U . . .
C16 C 0.69415(18) 0.39473(15) 0.9563(3) 0.0691(7) Uani 1 1 d D . . . .
H16A H 0.757958 0.394804 1.020903 0.083 Uiso 0.55 1 calc R U P A 1
H16B H 0.663245 0.386400 1.021840 0.083 Uiso 0.55 1 calc R U P A 1
H16C H 0.701432 0.371114 1.055179 0.083 Uiso 0.45 1 calc R U P B 2
H16D H 0.751051 0.420587 0.968936 0.083 Uiso 0.45 1 calc R U P B 2
C17' C 0.6678(6) 0.4848(5) 0.8753(12) 0.100(3) Uani 0.55 1 d D . P C 1
H17A H 0.701511 0.495284 0.816139 0.149 Uiso 0.55 1 calc R U P C 1
H17B H 0.679859 0.532664 0.949733 0.149 Uiso 0.55 1 calc R U P C 1
H17C H 0.605034 0.484161 0.808396 0.149 Uiso 0.55 1 calc R U P C 1
C17 C 0.6273(8) 0.4675(6) 0.9109(15) 0.120(5) Uani 0.45 1 d D . P C 2
H17D H 0.618613 0.490703 0.812134 0.180 Uiso 0.45 1 calc R U P C 2
H17E H 0.647699 0.515817 0.985263 0.180 Uiso 0.45 1 calc R U P C 2
H17F H 0.571773 0.443789 0.905667 0.180 Uiso 0.45 1 calc R U P C 2


_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 N1 2.0224(14) . ?
Ni1 N1 2.0224(14) 2_656 ?
Ni1 N11 2.0847(14) . ?
Ni1 N11 2.0848(14) 2_656 ?
Ni1 S1 2.5726(5) 6_556 ?
Ni1 S1 2.5726(5) 5_656 ?
S1 C1 1.6434(17) . ?
C1 N1 1.152(2) . ?
N11 C11 1.334(2) . ?
N11 C15 1.342(2) . ?
C11 C12 1.390(3) . ?
C12 C13 1.390(4) . ?
C12 C16 1.502(3) . ?
C13 C14 1.370(4) . ?
C14 C15 1.361(3) . ?
C16 C17 1.491(10) . ?
C16 C17' 1.532(7) . ?

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 Ni1 N1 176.28(8) . 2_656 ?
N1 Ni1 N11 90.55(6) . . ?
N1 Ni1 N11 92.01(6) 2_656 . ?
N1 Ni1 N11 92.01(5) . 2_656 ?
N1 Ni1 N11 90.55(6) 2_656 2_656 ?
N11 Ni1 N11 93.10(8) . 2_656 ?
N1 Ni1 S1 83.02(4) . 6_556 ?
N1 Ni1 S1 94.29(4) 2_656 6_556 ?
N11 Ni1 S1 173.02(4) . 6_556 ?
N11 Ni1 S1 89.85(4) 2_656 6_556 ?
N1 Ni1 S1 94.29(4) . 5_656 ?
N1 Ni1 S1 83.02(4) 2_656 5_656 ?
N11 Ni1 S1 89.85(4) . 5_656 ?
N11 Ni1 S1 173.02(4) 2_656 5_656 ?
S1 Ni1 S1 87.94(2) 6_556 5_656 ?
C1 S1 Ni1 99.92(5) . 5_656 ?
N1 C1 S1 178.75(15) . . ?
C1 N1 Ni1 166.06(13) . . ?
C11 N11 C15 118.32(16) . . ?
C11 N11 Ni1 121.34(12) . . ?
C15 N11 Ni1 120.32(13) . . ?
N11 C11 C12 123.60(18) . . ?
C13 C12 C11 116.3(2) . . ?
C13 C12 C16 123.1(2) . . ?
C11 C12 C16 120.6(2) . . ?
C14 C13 C12 120.2(2) . . ?
C15 C14 C13 119.5(2) . . ?
N11 C15 C14 122.0(2) . . ?
C17 C16 C12 114.6(5) . . ?
C12 C16 C17' 111.7(5) . . ?

_refine_diff_density_max         0.281
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.048



####################################################################### 
# 
# 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_cw1832
_database_code_depnum_ccdc_archive 'CCDC 1980436'
loop_
_audit_author_name
_audit_author_address
'Christian Naether'
;Kiel University
Germany
;
_audit_update_record             
;
2020-01-28 deposited with the CCDC.	2020-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 N4 Ni S2'
_chemical_formula_weight         389.17

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                   9.3096(19)
_cell_length_b                   10.516(2)
_cell_length_c                   11.057(2)
_cell_angle_alpha                68.06(3)
_cell_angle_beta                 66.94(3)
_cell_angle_gamma                69.49(3)
_cell_volume                     897.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    11792
_cell_measurement_theta_min      2.082
_cell_measurement_theta_max      25.999

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_F_000             404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    1.317
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_min  0.4940
_exptl_absorpt_correction_T_max  0.7034
_exptl_absorpt_process_details   'X-Shape and X-Red 32 (STOE, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'STOE IPDS-2'
_diffrn_measurement_method       'Omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11792
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.082
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3511
_reflns_number_gt                3042
_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       'X-Area (STOE, 2010)'
_computing_cell_refinement       'X-Area (STOE, 2010)'
_computing_data_reduction        'X-Area (STOE, 2010)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_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)+(0.0424P)²+0.1672P] 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         3511
_refine_ls_number_parameters     220
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0269
_refine_ls_wR_factor_ref         0.0743
_refine_ls_wR_factor_gt          0.0727
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.078
_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
Ni1 Ni 0.48347(3) 0.48523(2) 0.76362(2) 0.03308(9) Uani 1 1 d . . . . .
N1 N 0.36620(19) 0.58480(17) 0.91481(16) 0.0383(3) Uani 1 1 d . . . . .
C1 C 0.3635(2) 0.64134(18) 0.98772(18) 0.0336(4) Uani 1 1 d . . . . .
S1 S 0.36235(6) 0.72212(5) 1.08969(5) 0.04184(13) Uani 1 1 d . . . . .
N2 N 0.60910(19) 0.39801(16) 0.60530(16) 0.0378(3) Uani 1 1 d . . . . .
C2 C 0.6437(2) 0.36247(18) 0.50794(18) 0.0316(4) Uani 1 1 d . . . . .
S2 S 0.68883(6) 0.31297(5) 0.37049(5) 0.03861(12) Uani 1 1 d . . . . .
N11 N 0.30407(18) 0.37172(16) 0.83571(16) 0.0376(3) Uani 1 1 d . . . . .
C11 C 0.2835(2) 0.3133(2) 0.7568(2) 0.0425(4) Uani 1 1 d . . . . .
H11 H 0.355736 0.320067 0.666912 0.051 Uiso 1 1 calc R U . . .
C12 C 0.1641(3) 0.2437(2) 0.7976(2) 0.0453(5) Uani 1 1 d . . . . .
C13 C 0.0581(3) 0.2368(2) 0.9277(2) 0.0497(5) Uani 1 1 d . . . . .
H13 H -0.026719 0.190810 0.959999 0.060 Uiso 1 1 calc R U . . .
C14 C 0.0765(3) 0.2971(3) 1.0099(2) 0.0539(5) Uani 1 1 d . . . . .
H14 H 0.004057 0.293843 1.099324 0.065 Uiso 1 1 calc R U . . .
C15 C 0.2012(2) 0.3623(2) 0.9615(2) 0.0469(5) Uani 1 1 d . . . . .
H15 H 0.214249 0.402078 1.019705 0.056 Uiso 1 1 calc R U . . .
C16 C 0.1524(3) 0.1798(3) 0.7017(3) 0.0641(7) Uani 1 1 d . . . . .
H16A H 0.051764 0.231839 0.677208 0.077 Uiso 1 1 calc R U . . .
H16B H 0.243191 0.193352 0.616707 0.077 Uiso 1 1 calc R U . . .
C17 C 0.1544(6) 0.0308(3) 0.7551(4) 0.1222(15) Uani 1 1 d . . . . .
H17A H 0.247330 -0.020882 0.789248 0.183 Uiso 1 1 calc R U . . .
H17B H 0.161768 -0.004883 0.682148 0.183 Uiso 1 1 calc R U . . .
H17C H 0.055315 0.017544 0.829845 0.183 Uiso 1 1 calc R U . . .
N21 N 0.66063(18) 0.60090(16) 0.69764(16) 0.0373(3) Uani 1 1 d . . . . .
C21 C 0.6212(2) 0.7371(2) 0.6937(2) 0.0412(4) Uani 1 1 d . . . . .
H21 H 0.510579 0.784658 0.712087 0.049 Uiso 1 1 calc R U . . .
C22 C 0.7309(3) 0.8135(2) 0.6645(2) 0.0476(5) Uani 1 1 d . . . . .
C23 C 0.8913(3) 0.7418(2) 0.6387(2) 0.0517(5) Uani 1 1 d . . . . .
H23 H 0.971247 0.789035 0.619520 0.062 Uiso 1 1 calc R U . . .
C24 C 0.9344(3) 0.6023(2) 0.6408(2) 0.0521(5) Uani 1 1 d . . . . .
H24 H 1.044245 0.552506 0.622627 0.062 Uiso 1 1 calc R U . . .
C25 C 0.8170(2) 0.5354(2) 0.6697(2) 0.0444(4) Uani 1 1 d . . . . .
H25 H 0.847981 0.439164 0.669776 0.053 Uiso 1 1 calc R U . . .
C26 C 0.6744(3) 0.9673(2) 0.6627(3) 0.0670(7) Uani 1 1 d D . . . .
H26A H 0.759096 1.016039 0.594722 0.080 Uiso 0.8 1 calc R U P A 1
H26B H 0.577582 1.009573 0.631237 0.080 Uiso 0.8 1 calc R U P A 1
H26C H 0.567789 0.983351 0.731504 0.080 Uiso 0.2 1 calc R U P B 2
H26D H 0.662579 1.026014 0.571691 0.080 Uiso 0.2 1 calc R U P B 2
C27 C 0.6364(6) 0.9944(4) 0.7920(5) 0.0950(14) Uani 0.8 1 d D . P C 1
H27A H 0.556930 0.942581 0.861759 0.143 Uiso 0.8 1 calc R U P C 1
H27B H 0.592196 1.095804 0.782756 0.143 Uiso 0.8 1 calc R U P C 1
H27C H 0.734261 0.963240 0.819298 0.143 Uiso 0.8 1 calc R U P C 1
C27' C 0.795(2) 1.0128(13) 0.6942(18) 0.079(5) Uani 0.2 1 d D . P C 2
H27D H 0.833265 0.938068 0.767782 0.119 Uiso 0.2 1 calc R U P C 2
H27E H 0.741101 1.099995 0.722612 0.119 Uiso 0.2 1 calc R U P C 2
H27F H 0.886433 1.029112 0.611968 0.119 Uiso 0.2 1 calc R U P C 2


_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 N2 2.0293(18) . ?
Ni1 N1 2.0397(17) . ?
Ni1 N11 2.1196(17) . ?
Ni1 N21 2.1290(17) . ?
Ni1 S2 2.5298(12) 2_666 ?
Ni1 S1 2.5361(12) 2_667 ?
N1 C1 1.156(2) . ?
C1 S1 1.6409(18) . ?
N2 C2 1.160(2) . ?
C2 S2 1.6418(18) . ?
N11 C15 1.335(3) . ?
N11 C11 1.338(2) . ?
C11 C12 1.380(3) . ?
C12 C13 1.382(3) . ?
C12 C16 1.505(3) . ?
C13 C14 1.373(3) . ?
C14 C15 1.379(3) . ?
C16 C17 1.449(4) . ?
N21 C21 1.336(2) . ?
N21 C25 1.339(3) . ?
C21 C22 1.384(3) . ?
C22 C23 1.385(3) . ?
C22 C26 1.510(3) . ?
C23 C24 1.371(3) . ?
C24 C25 1.375(3) . ?
C26 C27 1.446(5) . ?
C26 C27' 1.555(11) . ?

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
N2 Ni1 N1 175.66(6) . . ?
N2 Ni1 N11 92.51(7) . . ?
N1 Ni1 N11 91.57(7) . . ?
N2 Ni1 N21 89.36(7) . . ?
N1 Ni1 N21 86.57(7) . . ?
N11 Ni1 N21 178.06(6) . . ?
N2 Ni1 S2 93.36(5) . 2_666 ?
N1 Ni1 S2 85.30(5) . 2_666 ?
N11 Ni1 S2 88.34(5) . 2_666 ?
N21 Ni1 S2 92.04(5) . 2_666 ?
N2 Ni1 S1 88.73(5) . 2_667 ?
N1 Ni1 S1 92.87(5) . 2_667 ?
N11 Ni1 S1 87.99(5) . 2_667 ?
N21 Ni1 S1 91.56(5) . 2_667 ?
S2 Ni1 S1 175.852(19) 2_666 2_667 ?
C1 N1 Ni1 152.25(14) . . ?
N1 C1 S1 179.14(17) . . ?
C1 S1 Ni1 98.56(7) . 2_667 ?
C2 N2 Ni1 162.55(14) . . ?
N2 C2 S2 178.84(15) . . ?
C2 S2 Ni1 102.15(7) . 2_666 ?
C15 N11 C11 117.34(17) . . ?
C15 N11 Ni1 120.28(13) . . ?
C11 N11 Ni1 122.29(13) . . ?
N11 C11 C12 124.21(19) . . ?
C11 C12 C13 117.33(19) . . ?
C11 C12 C16 120.2(2) . . ?
C13 C12 C16 122.5(2) . . ?
C14 C13 C12 119.3(2) . . ?
C13 C14 C15 119.4(2) . . ?
N11 C15 C14 122.38(19) . . ?
C17 C16 C12 115.0(2) . . ?
C21 N21 C25 117.38(17) . . ?
C21 N21 Ni1 121.97(13) . . ?
C25 N21 Ni1 120.41(13) . . ?
N21 C21 C22 124.29(19) . . ?
C21 C22 C23 116.79(19) . . ?
C21 C22 C26 120.4(2) . . ?
C23 C22 C26 122.8(2) . . ?
C24 C23 C22 119.8(2) . . ?
C23 C24 C25 119.3(2) . . ?
N21 C25 C24 122.43(19) . . ?
C27 C26 C22 115.4(3) . . ?
C22 C26 C27' 111.3(5) . . ?

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
_geom_hbond_publ_flag
C11 H11 N2 0.95 2.53 3.097(3) 118.7 . yes
C15 H15 N1 0.95 2.45 3.016(3) 118.2 . yes
C21 H21 S2 0.95 2.95 3.473(2) 116.0 2_666 yes
C25 H25 S1 0.95 2.94 3.392(3) 110.3 2_667 yes

_refine_diff_density_max         0.361
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_cw1246
_database_code_depnum_ccdc_archive 'CCDC 1980437'
loop_
_audit_author_name
_audit_author_address
'Christian Naether'
;Kiel University
Germany
;
_audit_update_record             
;
2020-01-28 deposited with the CCDC.	2020-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 N4 Ni S2'

_chemical_formula_sum            'C16 H18 N4 Ni S2'
_chemical_formula_weight         389.17

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                   10.1030(6)
_cell_length_b                   11.2150(6)
_cell_length_c                   18.5450(9)
_cell_angle_alpha                106.440(4)
_cell_angle_beta                 94.390(4)
_cell_angle_gamma                111.050(4)
_cell_volume                     1843.20(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    17026
_cell_measurement_theta_min      2.004
_cell_measurement_theta_max      27.044

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1332
_exptl_crystal_size_mid          0.0824
_exptl_crystal_size_min          0.0612
_exptl_absorpt_coefficient_mu    1.282
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7428
_exptl_absorpt_correction_T_max  0.8859
_exptl_absorpt_process_details   'X-Shape and X-Red 32 (STOE, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'STOE IPDS-2'
_diffrn_measurement_method       'Omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17026
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.004
_diffrn_reflns_theta_max         27.044
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             7957
_reflns_number_gt                6573
_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       'X-Area (STOE, 2010)'
_computing_cell_refinement       'X-Area (STOE, 2010)'
_computing_data_reduction        'X-Area (STOE, 2010)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_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)+(0.0572P)²+0.1279P] 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         7957
_refine_ls_number_parameters     418
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0928
_refine_ls_wR_factor_gt          0.0897
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.000
_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
Ni1 Ni 0.80148(3) 0.11071(3) 0.05038(2) 0.02762(8) Uani 1 1 d . . . . .
N1 N 0.9854(2) 0.14492(18) 0.00759(11) 0.0326(4) Uani 1 1 d . . . . .
C1 C 1.0865(2) 0.1380(2) -0.01563(12) 0.0296(4) Uani 1 1 d . . . . .
S1 S 1.22915(6) 0.12638(6) -0.04861(4) 0.03995(14) Uani 1 1 d . . . . .
N2 N 0.61018(19) 0.06338(19) 0.08620(10) 0.0313(4) Uani 1 1 d . . . . .
C2 C 0.4893(2) 0.0316(2) 0.08897(11) 0.0282(4) Uani 1 1 d . . . . .
S2 S 0.31696(6) -0.01422(6) 0.09196(3) 0.03663(13) Uani 1 1 d . . . . .
N11 N 0.8009(2) 0.29913(18) 0.05375(11) 0.0319(4) Uani 1 1 d . . . . .
C11 C 0.9230(3) 0.4110(2) 0.08008(13) 0.0344(5) Uani 1 1 d . . . . .
H11 H 1.010078 0.401913 0.094773 0.041 Uiso 1 1 calc R U . . .
C12 C 0.9300(3) 0.5402(2) 0.08725(14) 0.0407(5) Uani 1 1 d . . . . .
C13 C 0.8013(3) 0.5507(3) 0.06453(16) 0.0476(6) Uani 1 1 d . . . . .
H13 H 0.800206 0.636558 0.068230 0.057 Uiso 1 1 calc R U . . .
C14 C 0.6753(3) 0.4352(3) 0.03660(17) 0.0475(6) Uani 1 1 d . . . . .
H14 H 0.586947 0.440903 0.020339 0.057 Uiso 1 1 calc R U . . .
C15 C 0.6781(3) 0.3119(3) 0.03239(14) 0.0371(5) Uani 1 1 d . . . . .
H15 H 0.590381 0.233144 0.013774 0.045 Uiso 1 1 calc R U . . .
C16 C 1.0701(3) 0.6610(3) 0.11938(17) 0.0532(7) Uani 1 1 d . . . . .
H16A H 1.150751 0.631411 0.111642 0.064 Uiso 1 1 calc R U . . .
H16B H 1.076043 0.724319 0.090626 0.064 Uiso 1 1 calc R U . . .
C17 C 1.0883(6) 0.7333(6) 0.2012(3) 0.142(3) Uani 1 1 d . . . . .
H17A H 1.181768 0.811140 0.218828 0.213 Uiso 1 1 calc R U . . .
H17B H 1.010180 0.764985 0.209298 0.213 Uiso 1 1 calc R U . . .
H17C H 1.084947 0.672005 0.230331 0.213 Uiso 1 1 calc R U . . .
N21 N 0.9236(2) 0.19543(19) 0.16204(11) 0.0331(4) Uani 1 1 d . . . . .
C21 C 0.8872(3) 0.2761(3) 0.21761(14) 0.0417(5) Uani 1 1 d . . . . .
H21 H 0.797903 0.283829 0.206535 0.050 Uiso 1 1 calc R U . . .
C22 C 0.9714(3) 0.3486(3) 0.29005(16) 0.0512(6) Uani 1 1 d . . . . .
C23 C 1.0994(3) 0.3338(3) 0.30591(17) 0.0547(7) Uani 1 1 d . . . . .
H23 H 1.160737 0.381866 0.355120 0.066 Uiso 1 1 calc R U . . .
C24 C 1.1373(3) 0.2490(3) 0.25004(17) 0.0531(7) Uani 1 1 d . . . . .
H24 H 1.224383 0.236984 0.260420 0.064 Uiso 1 1 calc R U . . .
C25 C 1.0474(3) 0.1816(3) 0.17868(15) 0.0416(5) Uani 1 1 d . . . . .
H25 H 1.074286 0.123523 0.140117 0.050 Uiso 1 1 calc R U . . .
C26 C 0.9243(4) 0.4442(5) 0.34964(19) 0.0834(13) Uani 1 1 d . . . . .
H26A H 1.003626 0.535614 0.370415 0.100 Uiso 1 1 calc R U . . .
H26B H 0.838821 0.452255 0.325090 0.100 Uiso 1 1 calc R U . . .
C27 C 0.8892(7) 0.3902(8) 0.4108(3) 0.134(2) Uani 1 1 d . . . . .
H27A H 0.859118 0.450561 0.448955 0.201 Uiso 1 1 calc R U . . .
H27B H 0.810114 0.300145 0.389922 0.201 Uiso 1 1 calc R U . . .
H27C H 0.974454 0.383269 0.435119 0.201 Uiso 1 1 calc R U . . .
Ni2 Ni 0.500000 0.500000 0.500000 0.02796(9) Uani 1 2 d S . P . .
Ni3 Ni 0.500000 0.000000 0.500000 0.03085(10) Uani 1 2 d S . P . .
N3 N 0.3771(2) 0.09347(19) 0.46837(12) 0.0350(4) Uani 1 1 d . . . . .
C3 C 0.3311(2) 0.1747(2) 0.47058(12) 0.0304(4) Uani 1 1 d . . . . .
S3 S 0.26923(6) 0.29292(6) 0.47458(4) 0.03705(13) Uani 1 1 d . . . . .
N4 N 0.6259(2) 0.40447(18) 0.52473(11) 0.0327(4) Uani 1 1 d . . . . .
C4 C 0.6628(2) 0.3290(2) 0.54283(12) 0.0300(4) Uani 1 1 d . . . . .
S4 S 0.71413(7) 0.22191(6) 0.56926(4) 0.04174(15) Uani 1 1 d . . . . .
N31 N 0.4832(2) 0.56067(19) 0.61693(10) 0.0325(4) Uani 1 1 d . . . . .
C31 C 0.4765(3) 0.4799(2) 0.65939(14) 0.0390(5) Uani 1 1 d . . . . .
H31 H 0.474794 0.392564 0.634769 0.047 Uiso 1 1 calc R U . . .
C32 C 0.4718(3) 0.5161(3) 0.73654(14) 0.0428(5) Uani 1 1 d . . . . .
C33 C 0.4729(3) 0.6436(3) 0.77131(14) 0.0444(6) Uani 1 1 d . . . . .
H33 H 0.470698 0.673305 0.824353 0.053 Uiso 1 1 calc R U . . .
C34 C 0.4772(3) 0.7265(2) 0.72859(14) 0.0404(5) Uani 1 1 d . . . . .
H34 H 0.476267 0.813288 0.751598 0.048 Uiso 1 1 calc R U . . .
C35 C 0.4830(3) 0.6825(2) 0.65214(13) 0.0342(5) Uani 1 1 d . . . . .
H35 H 0.487026 0.741003 0.623229 0.041 Uiso 1 1 calc R U . . .
C36 C 0.4702(4) 0.4210(3) 0.78015(18) 0.0649(9) Uani 1 1 d . . . . .
H36A H 0.395410 0.416768 0.811991 0.078 Uiso 1 1 calc R U . . .
H36B H 0.443417 0.328902 0.743194 0.078 Uiso 1 1 calc R U . . .
C37 C 0.6137(7) 0.4639(6) 0.8309(3) 0.125(2) Uani 1 1 d . . . . .
H37A H 0.607126 0.399145 0.857931 0.188 Uiso 1 1 calc R U . . .
H37B H 0.687798 0.466414 0.799555 0.188 Uiso 1 1 calc R U . . .
H37C H 0.639786 0.554290 0.868359 0.188 Uiso 1 1 calc R U . . .
N41 N 0.5827(2) -0.0120(2) 0.39801(12) 0.0383(4) Uani 1 1 d . . . . .
C41 C 0.7177(3) -0.0026(3) 0.39741(16) 0.0436(6) Uani 1 1 d . . . . .
H41 H 0.777674 0.017566 0.444957 0.052 Uiso 1 1 calc R U . . .
C42 C 0.7770(3) -0.0204(3) 0.33187(17) 0.0498(6) Uani 1 1 d . . . . .
C43 C 0.6887(4) -0.0453(3) 0.26347(17) 0.0558(7) Uani 1 1 d . . . . .
H43 H 0.724312 -0.056218 0.217118 0.067 Uiso 1 1 calc R U . . .
C44 C 0.5489(4) -0.0543(3) 0.26341(16) 0.0547(7) Uani 1 1 d . . . . .
H44 H 0.487658 -0.071444 0.216918 0.066 Uiso 1 1 calc R U . . .
C45 C 0.4985(3) -0.0382(3) 0.33088(15) 0.0465(6) Uani 1 1 d . . . . .
H45 H 0.401625 -0.045838 0.330037 0.056 Uiso 1 1 calc R U . . .
C46 C 0.9299(4) -0.0128(4) 0.3377(2) 0.0701(9) Uani 1 1 d . . . . .
H46A H 0.953933 -0.028172 0.286045 0.084 Uiso 1 1 calc R U . . .
H46B H 0.997133 0.079460 0.370725 0.084 Uiso 1 1 calc R U . . .
C47 C 0.9526(5) -0.1138(6) 0.3699(3) 0.0923(14) Uani 1 1 d . . . . .
H47A H 1.053403 -0.103948 0.372273 0.138 Uiso 1 1 calc R U . . .
H47B H 0.931315 -0.097904 0.421615 0.138 Uiso 1 1 calc R U . . .
H47C H 0.888084 -0.205615 0.336873 0.138 Uiso 1 1 calc R U . . .


_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 N1 2.0288(18) . ?
Ni1 N2 2.0292(18) . ?
Ni1 N21 2.0894(19) . ?
Ni1 N11 2.0984(18) . ?
Ni1 S1 2.5544(6) 2_755 ?
Ni1 S2 2.5574(7) 2_655 ?
N1 C1 1.157(3) . ?
C1 S1 1.641(2) . ?
N2 C2 1.152(3) . ?
C2 S2 1.640(2) . ?
N11 C11 1.335(3) . ?
N11 C15 1.342(3) . ?
C11 C12 1.392(3) . ?
C12 C13 1.392(4) . ?
C12 C16 1.494(4) . ?
C13 C14 1.378(4) . ?
C14 C15 1.374(3) . ?
C16 C17 1.466(5) . ?
N21 C21 1.336(3) . ?
N21 C25 1.339(3) . ?
C21 C22 1.378(4) . ?
C22 C23 1.382(4) . ?
C22 C26 1.540(5) . ?
C23 C24 1.375(5) . ?
C24 C25 1.380(4) . ?
C26 C27 1.441(6) . ?
Ni2 N4 2.0356(19) 2_666 ?
Ni2 N4 2.0356(19) . ?
Ni2 N31 2.1210(18) 2_666 ?
Ni2 N31 2.1210(18) . ?
Ni2 S3 2.5246(6) 2_666 ?
Ni2 S3 2.5247(6) . ?
Ni3 N3 2.0387(19) 2_656 ?
Ni3 N3 2.0388(19) . ?
Ni3 N41 2.115(2) 2_656 ?
Ni3 N41 2.115(2) . ?
Ni3 S4 2.5340(6) . ?
Ni3 S4 2.5340(6) 2_656 ?
N3 C3 1.154(3) . ?
C3 S3 1.644(2) . ?
N4 C4 1.157(3) . ?
C4 S4 1.641(2) . ?
N31 C35 1.338(3) . ?
N31 C31 1.346(3) . ?
C31 C32 1.382(3) . ?
C32 C33 1.387(4) . ?
C32 C36 1.507(4) . ?
C33 C34 1.374(4) . ?
C34 C35 1.376(3) . ?
C36 C37 1.501(7) . ?
N41 C41 1.331(3) . ?
N41 C45 1.346(3) . ?
C41 C42 1.391(4) . ?
C42 C43 1.389(5) . ?
C42 C46 1.510(5) . ?
C43 C44 1.379(5) . ?
C44 C45 1.376(4) . ?
C46 C47 1.496(6) . ?

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 Ni1 N2 175.64(8) . . ?
N1 Ni1 N21 90.29(8) . . ?
N2 Ni1 N21 93.28(7) . . ?
N1 Ni1 N11 92.71(7) . . ?
N2 Ni1 N11 89.75(7) . . ?
N21 Ni1 N11 90.84(7) . . ?
N1 Ni1 S1 93.98(5) . 2_755 ?
N2 Ni1 S1 83.48(5) . 2_755 ?
N21 Ni1 S1 90.78(6) . 2_755 ?
N11 Ni1 S1 173.12(5) . 2_755 ?
N1 Ni1 S2 82.36(6) . 2_655 ?
N2 Ni1 S2 94.07(5) . 2_655 ?
N21 Ni1 S2 172.65(5) . 2_655 ?
N11 Ni1 S2 89.32(5) . 2_655 ?
S1 Ni1 S2 89.92(2) 2_755 2_655 ?
C1 N1 Ni1 165.52(17) . . ?
N1 C1 S1 179.31(19) . . ?
C1 S1 Ni1 101.16(7) . 2_755 ?
C2 N2 Ni1 163.98(17) . . ?
N2 C2 S2 179.42(18) . . ?
C2 S2 Ni1 102.14(7) . 2_655 ?
C11 N11 C15 118.1(2) . . ?
C11 N11 Ni1 120.48(15) . . ?
C15 N11 Ni1 121.38(16) . . ?
N11 C11 C12 123.8(2) . . ?
C11 C12 C13 117.0(2) . . ?
C11 C12 C16 120.6(2) . . ?
C13 C12 C16 122.3(2) . . ?
C14 C13 C12 119.3(2) . . ?
C15 C14 C13 119.7(3) . . ?
N11 C15 C14 122.0(2) . . ?
C17 C16 C12 113.4(3) . . ?
C21 N21 C25 117.7(2) . . ?
C21 N21 Ni1 120.55(16) . . ?
C25 N21 Ni1 121.41(17) . . ?
N21 C21 C22 124.0(2) . . ?
C21 C22 C23 117.4(3) . . ?
C21 C22 C26 120.6(3) . . ?
C23 C22 C26 122.1(3) . . ?
C24 C23 C22 119.6(3) . . ?
C23 C24 C25 119.2(3) . . ?
N21 C25 C24 122.1(3) . . ?
C27 C26 C22 109.0(4) . . ?
N4 Ni2 N4 180.00(11) 2_666 . ?
N4 Ni2 N31 89.51(7) 2_666 2_666 ?
N4 Ni2 N31 90.49(7) . 2_666 ?
N4 Ni2 N31 90.49(7) 2_666 . ?
N4 Ni2 N31 89.51(7) . . ?
N31 Ni2 N31 180.0 2_666 . ?
N4 Ni2 S3 92.71(5) 2_666 2_666 ?
N4 Ni2 S3 87.29(5) . 2_666 ?
N31 Ni2 S3 88.73(5) 2_666 2_666 ?
N31 Ni2 S3 91.27(5) . 2_666 ?
N4 Ni2 S3 87.29(5) 2_666 . ?
N4 Ni2 S3 92.71(5) . . ?
N31 Ni2 S3 91.27(5) 2_666 . ?
N31 Ni2 S3 88.73(5) . . ?
S3 Ni2 S3 180.0 2_666 . ?
N3 Ni3 N3 180.0 2_656 . ?
N3 Ni3 N41 90.62(8) 2_656 2_656 ?
N3 Ni3 N41 89.38(8) . 2_656 ?
N3 Ni3 N41 89.38(8) 2_656 . ?
N3 Ni3 N41 90.62(8) . . ?
N41 Ni3 N41 180.0 2_656 . ?
N3 Ni3 S4 86.85(6) 2_656 . ?
N3 Ni3 S4 93.15(6) . . ?
N41 Ni3 S4 90.14(6) 2_656 . ?
N41 Ni3 S4 89.86(6) . . ?
N3 Ni3 S4 93.15(6) 2_656 2_656 ?
N3 Ni3 S4 86.85(6) . 2_656 ?
N41 Ni3 S4 89.86(6) 2_656 2_656 ?
N41 Ni3 S4 90.14(6) . 2_656 ?
S4 Ni3 S4 180.0 . 2_656 ?
C3 N3 Ni3 159.94(19) . . ?
N3 C3 S3 178.7(2) . . ?
C3 S3 Ni2 101.85(8) . . ?
C4 N4 Ni2 161.46(18) . . ?
N4 C4 S4 179.3(2) . . ?
C4 S4 Ni3 101.21(8) . . ?
C35 N31 C31 117.2(2) . . ?
C35 N31 Ni2 121.30(14) . . ?
C31 N31 Ni2 121.45(16) . . ?
N31 C31 C32 124.1(2) . . ?
C31 C32 C33 117.1(2) . . ?
C31 C32 C36 120.4(2) . . ?
C33 C32 C36 122.5(2) . . ?
C34 C33 C32 119.6(2) . . ?
C33 C34 C35 119.3(2) . . ?
N31 C35 C34 122.6(2) . . ?
C37 C36 C32 112.6(3) . . ?
C41 N41 C45 117.8(2) . . ?
C41 N41 Ni3 120.64(17) . . ?
C45 N41 Ni3 121.41(18) . . ?
N41 C41 C42 124.4(3) . . ?
C43 C42 C41 116.7(3) . . ?
C43 C42 C46 123.6(3) . . ?
C41 C42 C46 119.7(3) . . ?
C44 C43 C42 119.4(3) . . ?
C45 C44 C43 119.8(3) . . ?
N41 C45 C44 121.8(3) . . ?
C47 C46 C42 113.3(3) . . ?

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
_geom_hbond_publ_flag
C35 H35 N4 0.95 2.67 3.128(3) 110.1 2_666 yes
C45 H45 N3 0.95 2.68 3.136(4) 110.0 . yes

_refine_diff_density_max         0.878
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.060

