# Supplementary Information (SI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_namiko163
_database_code_depnum_ccdc_archive 'CCDC 2288067'
loop_
_audit_author_name
_audit_author_address
'Namik Ozdemir'
;Ondokuz Mayis University
Turkey
;
_audit_update_record             
;
2023-08-10 deposited with the CCDC.	2024-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H9 Cl2 N3 O S'
_chemical_formula_sum            'C9 H9 Cl2 N3 O S'
_chemical_formula_weight         278.15

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'
Cl Cl 0.1484 0.1585 '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 0.0060 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.2672(5)
_cell_length_b                   7.9274(6)
_cell_length_c                   12.4219(9)
_cell_angle_alpha                82.624(6)
_cell_angle_beta                 78.692(6)
_cell_angle_gamma                76.836(6)
_cell_volume                     587.00(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9644
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      28.09

_exptl_crystal_description       prism
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_F_000             284
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.560
_exptl_crystal_size_min          0.530
_exptl_absorpt_coefficient_mu    0.712
_shelx_estimated_absorpt_T_min   0.636
_shelx_estimated_absorpt_T_max   0.704
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.6308
_exptl_absorpt_correction_T_max  0.7349
_exptl_absorpt_process_details   'X-RED32 (Stoe & Cie, 2002)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_collimation    '0.8 mm diameter, multiple pinhole'
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            6646
_diffrn_reflns_av_unetI/netI     0.0816
_diffrn_reflns_av_R_equivalents  0.1283
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.649
_diffrn_reflns_theta_max         27.693
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2751
_reflns_number_gt                2285
_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 & Cie, 2002)'
_computing_cell_refinement       X-AREA
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  
'OLEX2 (Dolomanov et al., 2009) and PLATON (Spek, 2009)'
_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)+(0.0780P)²+0.0678P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2751
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1566
_refine_ls_wR_factor_gt          0.1499
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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
Cl1 Cl 0.83703(12) 0.23877(12) 0.48752(5) 0.0716(3) Uani 1 1 d . . . . .
Cl2 Cl 1.30440(9) -0.03083(9) 0.11549(6) 0.0588(2) Uani 1 1 d . . . . .
S1 S -0.01432(10) 0.63369(9) 0.29672(5) 0.0536(2) Uani 1 1 d . . . . .
O1 O 0.4875(3) 0.3656(3) 0.35862(15) 0.0604(5) Uani 1 1 d . . . . .
H1 H 0.397508 0.409733 0.317934 0.091 Uiso 1 1 calc R U . . .
N1 N 0.3306(3) 0.4266(2) 0.17387(15) 0.0425(4) Uani 1 1 d . . . . .
N2 N 0.1702(3) 0.4921(3) 0.10803(16) 0.0455(4) Uani 1 1 d . . . . .
N3 N -0.1778(3) 0.6571(3) 0.10940(18) 0.0533(5) Uani 1 1 d . . . . .
H3A H -0.171508 0.636236 0.042466 0.064 Uiso 1 1 calc R U . . .
H3B H -0.295048 0.721533 0.143115 0.064 Uiso 1 1 calc R U . . .
C1 C 0.6715(4) 0.2763(3) 0.29981(19) 0.0434(5) Uani 1 1 d . . . . .
C2 C 0.8539(4) 0.2024(3) 0.35151(18) 0.0468(5) Uani 1 1 d . . . . .
C3 C 1.0480(4) 0.1081(3) 0.29633(19) 0.0464(5) Uani 1 1 d . . . . .
H3 H 1.168287 0.060964 0.332032 0.056 Uiso 1 1 calc R U . . .
C4 C 1.0598(3) 0.0852(3) 0.18737(19) 0.0427(5) Uani 1 1 d . . . . .
C5 C 0.8849(3) 0.1571(3) 0.13213(18) 0.0419(4) Uani 1 1 d . . . . .
H5 H 0.897319 0.141161 0.058094 0.050 Uiso 1 1 calc R U . . .
C6 C 0.6892(3) 0.2537(3) 0.18813(17) 0.0399(4) Uani 1 1 d . . . . .
C7 C 0.5100(3) 0.3334(3) 0.12694(18) 0.0414(4) Uani 1 1 d . . . . .
H7 H 0.526816 0.315996 0.052859 0.050 Uiso 1 1 calc R U . . .
C8 C -0.0047(3) 0.5890(3) 0.16124(18) 0.0420(4) Uani 1 1 d . . . . .
C9 C -0.2921(5) 0.7537(5) 0.3368(3) 0.0694(8) Uani 1 1 d . . . . .
H9A H -0.316752 0.859144 0.289262 0.104 Uiso 1 1 calc R U . . .
H9B H -0.312036 0.781469 0.411575 0.104 Uiso 1 1 calc R U . . .
H9C H -0.396281 0.684722 0.330998 0.104 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
Cl1 C2 1.729(2) . ?
Cl2 C4 1.739(2) . ?
S1 C8 1.751(2) . ?
S1 C9 1.792(3) . ?
O1 C1 1.340(3) . ?
O1 H1 0.8200 . ?
N1 C7 1.275(3) . ?
N1 N2 1.387(2) . ?
N2 C8 1.300(3) . ?
N3 C8 1.342(3) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
C1 C2 1.396(3) . ?
C1 C6 1.401(3) . ?
C2 C3 1.378(3) . ?
C3 C4 1.374(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(3) . ?
C5 C6 1.396(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.458(3) . ?
C7 H7 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

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
C8 S1 C9 104.28(13) . . ?
C1 O1 H1 109.5 . . ?
C7 N1 N2 115.52(18) . . ?
C8 N2 N1 111.57(18) . . ?
C8 N3 H3A 120.0 . . ?
C8 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
O1 C1 C2 118.9(2) . . ?
O1 C1 C6 122.80(19) . . ?
C2 C1 C6 118.3(2) . . ?
C3 C2 C1 122.1(2) . . ?
C3 C2 Cl1 119.53(17) . . ?
C1 C2 Cl1 118.37(18) . . ?
C4 C3 C2 118.5(2) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 C5 121.7(2) . . ?
C3 C4 Cl2 119.33(16) . . ?
C5 C4 Cl2 118.94(18) . . ?
C4 C5 C6 119.6(2) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C1 119.83(19) . . ?
C5 C6 C7 118.49(19) . . ?
C1 C6 C7 121.7(2) . . ?
N1 C7 C6 120.7(2) . . ?
N1 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
N2 C8 N3 118.5(2) . . ?
N2 C8 S1 121.16(16) . . ?
N3 C8 S1 120.30(18) . . ?
S1 C9 H9A 109.5 . . ?
S1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
S1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

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
C7 N1 N2 C8 -178.36(18) . . . . ?
O1 C1 C2 C3 179.6(2) . . . . ?
C6 C1 C2 C3 -0.4(3) . . . . ?
O1 C1 C2 Cl1 -2.9(3) . . . . ?
C6 C1 C2 Cl1 177.00(17) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
Cl1 C2 C3 C4 -178.12(18) . . . . ?
C2 C3 C4 C5 1.4(3) . . . . ?
C2 C3 C4 Cl2 179.11(17) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
Cl2 C4 C5 C6 -178.60(16) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
C4 C5 C6 C7 177.86(19) . . . . ?
O1 C1 C6 C5 -179.1(2) . . . . ?
C2 C1 C6 C5 0.9(3) . . . . ?
O1 C1 C6 C7 2.8(3) . . . . ?
C2 C1 C6 C7 -177.2(2) . . . . ?
N2 N1 C7 C6 -178.55(18) . . . . ?
C5 C6 C7 N1 -178.16(19) . . . . ?
C1 C6 C7 N1 0.0(3) . . . . ?
N1 N2 C8 N3 -177.78(19) . . . . ?
N1 N2 C8 S1 3.3(3) . . . . ?
C9 S1 C8 N2 -175.2(2) . . . . ?
C9 S1 C8 N3 5.9(2) . . . . ?

_refine_diff_density_max         0.518
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.075



####################################################################### 
# 
# 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_namiko165
_database_code_depnum_ccdc_archive 'CCDC 2288068'
loop_
_audit_author_name
_audit_author_address
'Namik Ozdemir'
;Ondokuz Mayis University
Turkey
;
_audit_update_record             
;
2023-08-10 deposited with the CCDC.	2024-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H18 Cl2 N4 Ni O3 S'
_chemical_formula_sum            'C13 H18 Cl2 N4 Ni O3 S'
_chemical_formula_weight         439.98

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

_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                   12.3415(8)
_cell_length_b                   10.1900(6)
_cell_length_c                   15.4159(11)
_cell_angle_alpha                90
_cell_angle_beta                 110.924(5)
_cell_angle_gamma                90
_cell_volume                     1810.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    11065
_cell_measurement_theta_min      2.00
_cell_measurement_theta_max      28.21

_exptl_crystal_description       prism
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.610
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    1.501
_shelx_estimated_absorpt_T_min   0.461
_shelx_estimated_absorpt_T_max   0.817
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.5773
_exptl_absorpt_correction_T_max  0.8088
_exptl_absorpt_process_details   'X-RED32 (Stoe & Cie, 2002)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_collimation    '0.8 mm diameter, multiple pinhole'
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            11650
_diffrn_reflns_av_unetI/netI     0.0704
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.449
_diffrn_reflns_theta_max         27.750
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4227
_reflns_number_gt                2528
_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 & Cie, 2002)'
_computing_cell_refinement       X-AREA
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  
'OLEX2 (Dolomanov et al., 2009) and PLATON (Spek, 2009)'
_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)+(0.0414P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4227
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1032
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1002
_refine_ls_wR_factor_gt          0.0867
_refine_ls_goodness_of_fit_ref   0.944
_refine_ls_restrained_S_all      0.944
_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 0.37200(4) 0.30322(5) 0.47979(3) 0.04087(14) Uani 1 1 d . . . . .
Cl1 Cl -0.01034(10) 0.38247(13) 0.28839(8) 0.0840(4) Uani 1 1 d . . . . .
Cl2 Cl -0.02017(12) 0.82059(14) 0.47922(11) 0.0970(5) Uani 1 1 d . . . . .
S1 S 0.71423(9) 0.28516(12) 0.69064(7) 0.0645(3) Uani 1 1 d . . . . .
O1 O 0.2245(2) 0.3597(2) 0.41677(16) 0.0499(6) Uani 1 1 d . . . . .
O2 O 0.4965(3) 0.1237(6) 0.3008(2) 0.1189(17) Uani 1 1 d . . . . .
H2 H 0.484569 0.077220 0.254915 0.178 Uiso 1 1 calc R U . . .
O3 O 0.3727(3) -0.0513(3) 0.52985(19) 0.0726(9) Uani 1 1 d . . . . .
H3 H 0.398940 -0.066303 0.585795 0.109 Uiso 1 1 calc R U . . .
N1 N 0.4096(2) 0.4366(3) 0.56614(18) 0.0414(7) Uani 1 1 d . . . . .
N2 N 0.5209(2) 0.4316(3) 0.63551(18) 0.0448(7) Uani 1 1 d . . . . .
N3 N 0.5214(3) 0.2520(3) 0.54541(19) 0.0488(8) Uani 1 1 d . . . . .
H3N H 0.553860 0.185192 0.530815 0.059 Uiso 1 1 calc R U . . .
N4 N 0.3356(3) 0.1497(3) 0.39868(18) 0.0448(7) Uani 1 1 d . . . . .
H4 H 0.404591 0.093530 0.418882 0.054 Uiso 1 1 calc R U . . .
C1 C 0.1732(3) 0.4620(4) 0.4350(2) 0.0445(8) Uani 1 1 d . . . . .
C2 C 0.0580(3) 0.4897(4) 0.3782(3) 0.0550(10) Uani 1 1 d . . . . .
C3 C 0.0000(4) 0.5979(4) 0.3918(3) 0.0666(12) Uani 1 1 d . . . . .
H3A H -0.076103 0.613612 0.352854 0.080 Uiso 1 1 calc R U . . .
C4 C 0.0550(4) 0.6834(4) 0.4635(3) 0.0633(11) Uani 1 1 d . . . . .
C5 C 0.1654(4) 0.6604(4) 0.5219(3) 0.0574(10) Uani 1 1 d . . . . .
H5 H 0.200631 0.717726 0.570812 0.069 Uiso 1 1 calc R U . . .
C6 C 0.2265(3) 0.5507(4) 0.5088(2) 0.0452(8) Uani 1 1 d . . . . .
C7 C 0.3436(3) 0.5319(4) 0.5716(2) 0.0496(9) Uani 1 1 d . . . . .
H7 H 0.373727 0.592473 0.619353 0.059 Uiso 1 1 calc R U . . .
C8 C 0.5736(3) 0.3279(4) 0.6169(2) 0.0436(9) Uani 1 1 d . . . . .
C9 C 0.7628(4) 0.4271(5) 0.7612(3) 0.0656(12) Uani 1 1 d . . . . .
H9A H 0.758488 0.502003 0.722276 0.098 Uiso 1 1 calc R U . . .
H9B H 0.841646 0.414501 0.801989 0.098 Uiso 1 1 calc R U . . .
H9C H 0.714572 0.441374 0.797224 0.098 Uiso 1 1 calc R U . . .
C10 C 0.3093(4) 0.1788(5) 0.2987(2) 0.0616(11) Uani 1 1 d . . . . .
H10A H 0.279590 0.100199 0.262579 0.074 Uiso 1 1 calc R U . . .
H10B H 0.249316 0.245435 0.278752 0.074 Uiso 1 1 calc R U . . .
C11 C 0.4105(5) 0.2243(6) 0.2803(3) 0.0851(16) Uani 1 1 d . . . . .
H11A H 0.388032 0.249477 0.215602 0.102 Uiso 1 1 calc R U . . .
H11B H 0.442563 0.300997 0.318116 0.102 Uiso 1 1 calc R U . . .
C12 C 0.2407(3) 0.0727(4) 0.4107(3) 0.0557(10) Uani 1 1 d . . . . .
H12A H 0.223829 -0.002532 0.369460 0.067 Uiso 1 1 calc R U . . .
H12B H 0.171335 0.126373 0.394034 0.067 Uiso 1 1 calc R U . . .
C13 C 0.2725(4) 0.0268(4) 0.5086(3) 0.0591(11) Uani 1 1 d . . . . .
H13A H 0.287460 0.101349 0.550422 0.071 Uiso 1 1 calc R U . . .
H13B H 0.209468 -0.023995 0.515404 0.071 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 O1 1.824(2) . ?
Ni1 N3 1.834(3) . ?
Ni1 N1 1.842(3) . ?
Ni1 N4 1.953(3) . ?
Cl1 C2 1.728(4) . ?
Cl2 C4 1.742(4) . ?
S1 C8 1.757(3) . ?
S1 C9 1.780(4) . ?
O1 C1 1.302(4) . ?
O2 C11 1.428(6) . ?
O2 H2 0.8200 . ?
O3 C13 1.408(5) . ?
O3 H3 0.8200 . ?
N1 C7 1.291(4) . ?
N1 N2 1.408(4) . ?
N2 C8 1.325(4) . ?
N3 C8 1.311(4) . ?
N3 H3N 0.8600 . ?
N4 C12 1.474(5) . ?
N4 C10 1.487(4) . ?
N4 H4 0.9800 . ?
C1 C2 1.406(5) . ?
C1 C6 1.417(5) . ?
C2 C3 1.371(6) . ?
C3 C4 1.381(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.358(6) . ?
C5 C6 1.403(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.436(5) . ?
C7 H7 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.452(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.493(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?

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
O1 Ni1 N3 177.96(13) . . ?
O1 Ni1 N1 95.65(12) . . ?
N3 Ni1 N1 82.34(13) . . ?
O1 Ni1 N4 87.35(12) . . ?
N3 Ni1 N4 94.68(13) . . ?
N1 Ni1 N4 174.26(12) . . ?
C8 S1 C9 103.5(2) . . ?
C1 O1 Ni1 127.4(2) . . ?
C11 O2 H2 109.5 . . ?
C13 O3 H3 109.5 . . ?
C7 N1 N2 116.4(3) . . ?
C7 N1 Ni1 126.9(2) . . ?
N2 N1 Ni1 116.6(2) . . ?
C8 N2 N1 106.6(3) . . ?
C8 N3 Ni1 113.0(2) . . ?
C8 N3 H3N 123.5 . . ?
Ni1 N3 H3N 123.5 . . ?
C12 N4 C10 110.3(3) . . ?
C12 N4 Ni1 110.9(2) . . ?
C10 N4 Ni1 114.7(2) . . ?
C12 N4 H4 106.8 . . ?
C10 N4 H4 106.8 . . ?
Ni1 N4 H4 106.8 . . ?
O1 C1 C2 119.2(3) . . ?
O1 C1 C6 124.2(3) . . ?
C2 C1 C6 116.7(3) . . ?
C3 C2 C1 122.2(4) . . ?
C3 C2 Cl1 119.9(3) . . ?
C1 C2 Cl1 117.9(3) . . ?
C2 C3 C4 119.7(4) . . ?
C2 C3 H3A 120.2 . . ?
C4 C3 H3A 120.2 . . ?
C5 C4 C3 120.8(4) . . ?
C5 C4 Cl2 120.3(4) . . ?
C3 C4 Cl2 118.9(3) . . ?
C4 C5 C6 120.4(4) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 120.2(3) . . ?
C5 C6 C7 118.2(3) . . ?
C1 C6 C7 121.6(3) . . ?
N1 C7 C6 124.3(3) . . ?
N1 C7 H7 117.9 . . ?
C6 C7 H7 117.9 . . ?
N3 C8 N2 121.4(3) . . ?
N3 C8 S1 118.2(3) . . ?
N2 C8 S1 120.3(3) . . ?
S1 C9 H9A 109.5 . . ?
S1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
S1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 N4 112.4(3) . . ?
C11 C10 H10A 109.1 . . ?
N4 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
N4 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
O2 C11 C10 110.5(5) . . ?
O2 C11 H11A 109.5 . . ?
C10 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
N4 C12 C13 111.1(3) . . ?
N4 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
N4 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
O3 C13 C12 107.7(3) . . ?
O3 C13 H13A 110.2 . . ?
C12 C13 H13A 110.2 . . ?
O3 C13 H13B 110.2 . . ?
C12 C13 H13B 110.2 . . ?
H13A C13 H13B 108.5 . . ?

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
N1 Ni1 O1 C1 -0.5(3) . . . . ?
N4 Ni1 O1 C1 174.5(3) . . . . ?
O1 Ni1 N1 C7 0.2(3) . . . . ?
N3 Ni1 N1 C7 179.9(3) . . . . ?
O1 Ni1 N1 N2 177.9(2) . . . . ?
N3 Ni1 N1 N2 -2.5(2) . . . . ?
C7 N1 N2 C8 -179.9(3) . . . . ?
Ni1 N1 N2 C8 2.2(3) . . . . ?
N1 Ni1 N3 C8 2.1(3) . . . . ?
N4 Ni1 N3 C8 -172.9(3) . . . . ?
Ni1 O1 C1 C2 -179.8(3) . . . . ?
Ni1 O1 C1 C6 1.1(5) . . . . ?
O1 C1 C2 C3 -178.0(4) . . . . ?
C6 C1 C2 C3 1.1(6) . . . . ?
O1 C1 C2 Cl1 1.7(5) . . . . ?
C6 C1 C2 Cl1 -179.2(3) . . . . ?
C1 C2 C3 C4 -0.2(6) . . . . ?
Cl1 C2 C3 C4 -179.9(3) . . . . ?
C2 C3 C4 C5 -1.2(7) . . . . ?
C2 C3 C4 Cl2 179.7(3) . . . . ?
C3 C4 C5 C6 1.6(7) . . . . ?
Cl2 C4 C5 C6 -179.3(3) . . . . ?
C4 C5 C6 C1 -0.6(6) . . . . ?
C4 C5 C6 C7 179.1(4) . . . . ?
O1 C1 C6 C5 178.4(3) . . . . ?
C2 C1 C6 C5 -0.7(5) . . . . ?
O1 C1 C6 C7 -1.3(6) . . . . ?
C2 C1 C6 C7 179.6(4) . . . . ?
N2 N1 C7 C6 -178.2(3) . . . . ?
Ni1 N1 C7 C6 -0.5(5) . . . . ?
C5 C6 C7 N1 -178.7(4) . . . . ?
C1 C6 C7 N1 1.0(6) . . . . ?
Ni1 N3 C8 N2 -1.5(4) . . . . ?
Ni1 N3 C8 S1 176.13(18) . . . . ?
N1 N2 C8 N3 -0.4(5) . . . . ?
N1 N2 C8 S1 -178.0(2) . . . . ?
C9 S1 C8 N3 168.3(3) . . . . ?
C9 S1 C8 N2 -14.0(3) . . . . ?
C12 N4 C10 C11 -165.4(4) . . . . ?
Ni1 N4 C10 C11 68.5(4) . . . . ?
N4 C10 C11 O2 64.2(5) . . . . ?
C10 N4 C12 C13 172.2(3) . . . . ?
Ni1 N4 C12 C13 -59.5(4) . . . . ?
N4 C12 C13 O3 -59.5(4) . . . . ?

_refine_diff_density_max         0.410
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.066



####################################################################### 
# 
# 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_namiko281
_database_code_depnum_ccdc_archive 'CCDC 2288069'
loop_
_audit_author_name
_audit_author_address
'Namik Ozdemir'
;Ondokuz Mayis University
Turkey
;
_audit_update_record             
;
2023-08-10 deposited with the CCDC.	2024-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H18 Br2 N4 Ni O3 S'
_chemical_formula_sum            'C13 H18 Br2 N4 Ni O3 S'
_chemical_formula_weight         528.90

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

_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                   12.6900(8)
_cell_length_b                   10.2688(5)
_cell_length_c                   15.4499(12)
_cell_angle_alpha                90
_cell_angle_beta                 111.571(5)
_cell_angle_gamma                90
_cell_volume                     1872.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    17350
_cell_measurement_theta_min      1.98
_cell_measurement_theta_max      28.11

_exptl_crystal_description       prism
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.876
_exptl_crystal_F_000             1048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.740
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    5.435
_shelx_estimated_absorpt_T_min   0.108
_shelx_estimated_absorpt_T_max   0.395
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.0300
_exptl_absorpt_correction_T_max  0.3556
_exptl_absorpt_process_details   'X-RED32 (Stoe & Cie, 2002)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_collimation    '0.8 mm diameter, multiple pinhole'
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            15384
_diffrn_reflns_av_unetI/netI     0.0634
_diffrn_reflns_av_R_equivalents  0.0812
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.438
_diffrn_reflns_theta_max         27.760
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4379
_reflns_number_gt                3039
_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 & Cie, 2002)'
_computing_cell_refinement       X-AREA
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  
'OLEX2 (Dolomanov et al., 2009) and PLATON (Spek, 2009)'
_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)+(0.0551P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4379
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1171
_refine_ls_wR_factor_gt          0.1057
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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 0.62669(5) 0.30247(5) 0.52219(4) 0.03437(15) Uani 1 1 d . . . . .
Br1 Br 1.00907(5) 0.36580(6) 0.72432(5) 0.0664(2) Uani 1 1 d . . . . .
Br2 Br 1.02504(6) 0.82002(6) 0.52046(5) 0.0724(2) Uani 1 1 d . . . . .
S1 S 0.28941(11) 0.28946(13) 0.31015(10) 0.0575(4) Uani 1 1 d . . . . .
O1 O 0.7720(3) 0.3568(3) 0.5860(2) 0.0424(7) Uani 1 1 d . . . . .
O2 O 0.5000(5) 0.1301(7) 0.6989(3) 0.108(2) Uani 1 1 d . . . . .
H2 H 0.524171 0.067200 0.733233 0.162 Uiso 1 1 calc R U . . .
O3 O 0.6243(4) -0.0504(4) 0.4722(3) 0.0669(11) Uani 1 1 d . . . . .
H3 H 0.602619 -0.071983 0.417323 0.100 Uiso 1 1 calc R U . . .
N1 N 0.5908(3) 0.4356(3) 0.4350(3) 0.0366(8) Uani 1 1 d . . . . .
N2 N 0.4812(3) 0.4323(3) 0.3656(3) 0.0396(8) Uani 1 1 d . . . . .
N3 N 0.4788(3) 0.2543(4) 0.4561(3) 0.0462(9) Uani 1 1 d . . . . .
H3N H 0.446229 0.189144 0.470775 0.055 Uiso 1 1 calc R U . . .
N4 N 0.6610(3) 0.1490(3) 0.6042(3) 0.0401(8) Uani 1 1 d . . . . .
H4 H 0.593254 0.093822 0.583334 0.048 Uiso 1 1 calc R U . . .
C1 C 0.8230(4) 0.4571(4) 0.5677(3) 0.0366(9) Uani 1 1 d . . . . .
C2 C 0.9375(4) 0.4833(4) 0.6248(4) 0.0444(11) Uani 1 1 d . . . . .
C3 C 0.9965(4) 0.5890(4) 0.6108(4) 0.0489(12) Uani 1 1 d . . . . .
H3A H 1.071026 0.603968 0.650206 0.059 Uiso 1 1 calc R U . . .
C4 C 0.9435(4) 0.6723(4) 0.5376(4) 0.0497(12) Uani 1 1 d . . . . .
C5 C 0.8340(4) 0.6520(4) 0.4789(4) 0.0472(11) Uani 1 1 d . . . . .
H5 H 0.800169 0.709253 0.429877 0.057 Uiso 1 1 calc R U . . .
C6 C 0.7720(4) 0.5448(4) 0.4920(3) 0.0389(10) Uani 1 1 d . . . . .
C7 C 0.6571(4) 0.5282(4) 0.4290(4) 0.0447(11) Uani 1 1 d . . . . .
H7 H 0.628428 0.587769 0.380699 0.054 Uiso 1 1 calc R U . . .
C8 C 0.4285(4) 0.3299(4) 0.3842(3) 0.0403(10) Uani 1 1 d . . . . .
C9 C 0.2422(5) 0.4295(6) 0.2365(4) 0.0589(14) Uani 1 1 d . . . . .
H9A H 0.248129 0.505494 0.274210 0.088 Uiso 1 1 calc R U . . .
H9B H 0.164757 0.417462 0.195959 0.088 Uiso 1 1 calc R U . . .
H9C H 0.288590 0.440504 0.199971 0.088 Uiso 1 1 calc R U . . .
C10 C 0.6869(5) 0.1789(5) 0.7045(4) 0.0524(12) Uani 1 1 d . . . . .
H10A H 0.714064 0.100690 0.741196 0.063 Uiso 1 1 calc R U . . .
H10B H 0.746516 0.243757 0.725272 0.063 Uiso 1 1 calc R U . . .
C11 C 0.5861(6) 0.2277(7) 0.7198(4) 0.0696(16) Uani 1 1 d . . . . .
H11A H 0.607238 0.254628 0.784139 0.083 Uiso 1 1 calc R U . . .
H11B H 0.556508 0.303195 0.680635 0.083 Uiso 1 1 calc R U . . .
C12 C 0.7542(4) 0.0711(4) 0.5938(4) 0.0488(12) Uani 1 1 d . . . . .
H12A H 0.769819 -0.003577 0.635033 0.059 Uiso 1 1 calc R U . . .
H12B H 0.822405 0.123726 0.611531 0.059 Uiso 1 1 calc R U . . .
C13 C 0.7234(5) 0.0250(5) 0.4946(4) 0.0552(13) Uani 1 1 d . . . . .
H13A H 0.710245 0.098877 0.452845 0.066 Uiso 1 1 calc R U . . .
H13B H 0.784454 -0.026902 0.488939 0.066 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 O1 1.830(3) . ?
Ni1 N3 1.844(4) . ?
Ni1 N1 1.855(3) . ?
Ni1 N4 1.968(3) . ?
Br1 C2 1.901(5) . ?
Br2 C4 1.908(4) . ?
S1 C8 1.764(5) . ?
S1 C9 1.795(6) . ?
O1 C1 1.302(5) . ?
O2 C11 1.429(8) . ?
O2 H2 0.8200 . ?
O3 C13 1.407(6) . ?
O3 H3 0.8200 . ?
N1 C7 1.296(6) . ?
N1 N2 1.410(5) . ?
N2 C8 1.333(6) . ?
N3 C8 1.312(6) . ?
N3 H3N 0.8600 . ?
N4 C12 1.484(6) . ?
N4 C10 1.494(6) . ?
N4 H4 0.9800 . ?
C1 C2 1.421(6) . ?
C1 C6 1.428(6) . ?
C2 C3 1.380(7) . ?
C3 C4 1.380(8) . ?
C3 H3A 0.9300 . ?
C4 C5 1.367(7) . ?
C5 C6 1.410(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.434(6) . ?
C7 H7 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.472(9) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.511(8) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?

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
O1 Ni1 N3 177.72(15) . . ?
O1 Ni1 N1 95.54(14) . . ?
N3 Ni1 N1 82.35(16) . . ?
O1 Ni1 N4 87.51(14) . . ?
N3 Ni1 N4 94.66(16) . . ?
N1 Ni1 N4 174.25(16) . . ?
C8 S1 C9 104.1(2) . . ?
C1 O1 Ni1 127.4(3) . . ?
C11 O2 H2 109.5 . . ?
C13 O3 H3 109.5 . . ?
C7 N1 N2 116.7(4) . . ?
C7 N1 Ni1 126.9(3) . . ?
N2 N1 Ni1 116.4(3) . . ?
C8 N2 N1 106.8(3) . . ?
C8 N3 Ni1 112.9(3) . . ?
C8 N3 H3N 123.5 . . ?
Ni1 N3 H3N 123.5 . . ?
C12 N4 C10 110.1(4) . . ?
C12 N4 Ni1 111.0(3) . . ?
C10 N4 Ni1 114.5(3) . . ?
C12 N4 H4 106.9 . . ?
C10 N4 H4 106.9 . . ?
Ni1 N4 H4 106.9 . . ?
O1 C1 C2 119.4(4) . . ?
O1 C1 C6 124.4(4) . . ?
C2 C1 C6 116.2(4) . . ?
C3 C2 C1 122.7(4) . . ?
C3 C2 Br1 120.1(4) . . ?
C1 C2 Br1 117.2(3) . . ?
C4 C3 C2 119.2(5) . . ?
C4 C3 H3A 120.4 . . ?
C2 C3 H3A 120.4 . . ?
C5 C4 C3 121.3(4) . . ?
C5 C4 Br2 120.0(4) . . ?
C3 C4 Br2 118.7(4) . . ?
C4 C5 C6 120.6(4) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 120.0(4) . . ?
C5 C6 C7 118.5(4) . . ?
C1 C6 C7 121.5(4) . . ?
N1 C7 C6 124.3(4) . . ?
N1 C7 H7 117.8 . . ?
C6 C7 H7 117.8 . . ?
N3 C8 N2 121.5(4) . . ?
N3 C8 S1 118.0(3) . . ?
N2 C8 S1 120.5(3) . . ?
S1 C9 H9A 109.5 . . ?
S1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
S1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 N4 111.4(4) . . ?
C11 C10 H10A 109.4 . . ?
N4 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
N4 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
O2 C11 C10 111.2(6) . . ?
O2 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 . . ?
O2 C11 H11B 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
N4 C12 C13 111.0(4) . . ?
N4 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
N4 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
O3 C13 C12 107.2(5) . . ?
O3 C13 H13A 110.3 . . ?
C12 C13 H13A 110.3 . . ?
O3 C13 H13B 110.3 . . ?
C12 C13 H13B 110.3 . . ?
H13A C13 H13B 108.5 . . ?

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
N1 Ni1 O1 C1 -0.8(4) . . . . ?
N4 Ni1 O1 C1 174.3(4) . . . . ?
O1 Ni1 N1 C7 1.3(5) . . . . ?
N3 Ni1 N1 C7 -179.5(5) . . . . ?
O1 Ni1 N1 N2 178.5(3) . . . . ?
N3 Ni1 N1 N2 -2.4(3) . . . . ?
C7 N1 N2 C8 179.3(4) . . . . ?
Ni1 N1 N2 C8 1.9(5) . . . . ?
N1 Ni1 N3 C8 2.3(4) . . . . ?
N4 Ni1 N3 C8 -172.7(4) . . . . ?
Ni1 O1 C1 C2 -179.2(3) . . . . ?
Ni1 O1 C1 C6 0.3(7) . . . . ?
O1 C1 C2 C3 -178.7(5) . . . . ?
C6 C1 C2 C3 1.7(7) . . . . ?
O1 C1 C2 Br1 1.0(6) . . . . ?
C6 C1 C2 Br1 -178.5(3) . . . . ?
C1 C2 C3 C4 -1.0(8) . . . . ?
Br1 C2 C3 C4 179.3(4) . . . . ?
C2 C3 C4 C5 0.0(8) . . . . ?
C2 C3 C4 Br2 178.8(4) . . . . ?
C3 C4 C5 C6 0.2(8) . . . . ?
Br2 C4 C5 C6 -178.6(4) . . . . ?
C4 C5 C6 C1 0.6(8) . . . . ?
C4 C5 C6 C7 179.6(5) . . . . ?
O1 C1 C6 C5 179.0(5) . . . . ?
C2 C1 C6 C5 -1.5(7) . . . . ?
O1 C1 C6 C7 0.0(7) . . . . ?
C2 C1 C6 C7 179.5(5) . . . . ?
N2 N1 C7 C6 -178.5(4) . . . . ?
Ni1 N1 C7 C6 -1.4(8) . . . . ?
C5 C6 C7 N1 -178.4(5) . . . . ?
C1 C6 C7 N1 0.6(8) . . . . ?
Ni1 N3 C8 N2 -2.1(6) . . . . ?
Ni1 N3 C8 S1 176.1(2) . . . . ?
N1 N2 C8 N3 0.2(6) . . . . ?
N1 N2 C8 S1 -178.0(3) . . . . ?
C9 S1 C8 N3 169.2(4) . . . . ?
C9 S1 C8 N2 -12.6(5) . . . . ?
C12 N4 C10 C11 -166.3(4) . . . . ?
Ni1 N4 C10 C11 67.7(5) . . . . ?
N4 C10 C11 O2 64.9(6) . . . . ?
C10 N4 C12 C13 172.7(4) . . . . ?
Ni1 N4 C12 C13 -59.4(4) . . . . ?
N4 C12 C13 O3 -59.0(5) . . . . ?

_refine_diff_density_max         0.833
_refine_diff_density_min         -0.551
_refine_diff_density_rms         0.128



