# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2023

####################################################################### 
# 
# 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_sun14neu
_database_code_depnum_ccdc_archive 'CCDC 1865447'
loop_
_audit_author_name
_audit_author_address
li
;shandong university
China
;
_audit_update_record             
;
2023-05-22 deposited with the CCDC.	2023-05-24 downloaded from the CCDC.
;
_audit_creation_date             2018-08-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H21 Cl N4 Ni'
_chemical_formula_sum            'C22 H21 Cl N4 Ni'
_chemical_formula_weight         435.59
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 '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 0.3294 0.5404 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -1.3412 3.2906 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   22.2059(5)
_cell_length_b                   10.1482(2)
_cell_length_c                   8.5616(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1929.36(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    29360
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      61.67
_cell_measurement_theta_min      1.73
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.518
_exptl_absorpt_correction_T_max  0.1538
_exptl_absorpt_correction_T_min  0.1061
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0128
_diffrn_reflns_av_unetI/netI     0.0107
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10895
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        53.597
_diffrn_reflns_theta_max         59.966
_diffrn_reflns_theta_min         3.463
_diffrn_ambient_temperature      150.15
_diffrn_detector                 'Eiger R 1M'
_diffrn_detector_area_resol_mean 13.33
_diffrn_detector_type            DECTRIS
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '1.2 0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34143
_diffrn_source                   'Metaljet D2'
_diffrn_source_current           2.860
_diffrn_source_power             0.200
_diffrn_source_target            Ga
_diffrn_source_type              'Metaljet D2'
_diffrn_source_voltage           70
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.809
_reflns_Friedel_fraction_full    0.948
_reflns_Friedel_fraction_max     0.911
_reflns_number_gt                4007
_reflns_number_total             4120
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.001(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4120
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0263
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0474P)²+0.6352P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0713
_refine_ls_wR_factor_ref         0.0718
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 -0.37208(2) -0.32019(3) -0.24430(5) 0.02182(11) Uani 1 1 d . . . . .
Cl1 Cl -0.43051(3) -0.18555(6) -0.11260(8) 0.02995(16) Uani 1 1 d . . . . .
N1 N -0.29874(10) -0.2488(2) -0.1529(3) 0.0255(4) Uani 1 1 d . . . . .
N2 N -0.32160(10) -0.4538(2) -0.3181(3) 0.0259(4) Uani 1 1 d . . . . .
N3 N -0.43693(10) -0.5100(2) -0.4275(3) 0.0259(5) Uani 1 1 d . . . . .
N4 N -0.47688(11) -0.3186(2) -0.4586(3) 0.0277(5) Uani 1 1 d . . . . .
C1 C -0.29149(14) -0.1449(3) -0.0619(3) 0.0308(6) Uani 1 1 d . . . . .
H1 H -0.326021 -0.101791 -0.020915 0.037 Uiso 1 1 calc R . . . .
C2 C -0.23365(14) -0.0962(3) -0.0239(4) 0.0385(7) Uani 1 1 d . . . . .
H2 H -0.229740 -0.021314 0.042009 0.046 Uiso 1 1 calc R . . . .
C3 C -0.18373(15) -0.1561(4) -0.0813(4) 0.0400(7) Uani 1 1 d . . . . .
H3 H -0.144945 -0.123106 -0.055572 0.048 Uiso 1 1 calc R . . . .
C4 C -0.18925(13) -0.2673(3) -0.1789(3) 0.0324(6) Uani 1 1 d . . . . .
C5 C -0.14112(13) -0.3358(3) -0.2492(5) 0.0397(7) Uani 1 1 d . . . . .
H5 H -0.100758 -0.309204 -0.230289 0.048 Uiso 1 1 calc R . . . .
C6 C -0.15273(14) -0.4408(4) -0.3448(4) 0.0397(7) Uani 1 1 d . . . . .
H6 H -0.119986 -0.484622 -0.393782 0.048 Uiso 1 1 calc R . . . .
C7 C -0.21216(13) -0.4861(3) -0.3731(4) 0.0340(6) Uani 1 1 d . . . . .
H7 H -0.218876 -0.559361 -0.439969 0.041 Uiso 1 1 calc R . . . .
C8 C -0.26035(12) -0.4229(3) -0.3026(3) 0.0272(5) Uani 1 1 d . . . . .
C9 C -0.24890(13) -0.3118(3) -0.2097(3) 0.0262(6) Uani 1 1 d . . . . .
C10 C -0.34022(13) -0.5835(3) -0.3251(3) 0.0262(5) Uani 1 1 d . . . . .
C11 C -0.39845(13) -0.6143(3) -0.3780(3) 0.0269(5) Uani 1 1 d . . . . .
C12 C -0.42010(15) -0.7434(3) -0.3809(3) 0.0332(6) Uani 1 1 d . . . . .
H12 H -0.459820 -0.760593 -0.416674 0.040 Uiso 1 1 calc R . . . .
C13 C -0.38386(17) -0.8465(3) -0.3316(4) 0.0376(7) Uani 1 1 d . . . . .
H13 H -0.397987 -0.934801 -0.335822 0.045 Uiso 1 1 calc R . . . .
C14 C -0.32603(17) -0.8182(3) -0.2756(4) 0.0364(7) Uani 1 1 d . . . . .
H14 H -0.301031 -0.887788 -0.239590 0.044 Uiso 1 1 calc R . . . .
C15 C -0.30494(14) -0.6902(3) -0.2721(3) 0.0305(6) Uani 1 1 d . . . . .
H15 H -0.265639 -0.673582 -0.232966 0.037 Uiso 1 1 calc R . . . .
C16 C -0.43264(11) -0.3825(3) -0.3786(3) 0.0248(5) Uani 1 1 d . . . . .
C17 C -0.48350(13) -0.5249(3) -0.5338(3) 0.0316(6) Uani 1 1 d . . . . .
H17 H -0.495670 -0.604417 -0.583227 0.038 Uiso 1 1 calc R . . . .
C18 C -0.50776(13) -0.4066(3) -0.5532(3) 0.0335(6) Uani 1 1 d . . . . .
H18 H -0.540544 -0.385827 -0.620103 0.040 Uiso 1 1 calc R . . . .
C19 C -0.48975(14) -0.1769(3) -0.4630(4) 0.0345(7) Uani 1 1 d . . . . .
H19A H -0.476598 -0.140900 -0.564902 0.041 Uiso 1 1 calc R . . . .
H19B H -0.466229 -0.132338 -0.380218 0.041 Uiso 1 1 calc R . . . .
C20 C -0.55608(16) -0.1469(4) -0.4399(5) 0.0453(8) Uani 1 1 d . . . . .
H20A H -0.579116 -0.190939 -0.524060 0.054 Uiso 1 1 calc R . . . .
H20B H -0.562133 -0.050806 -0.451643 0.054 Uiso 1 1 calc R . . . .
C21 C -0.58212(17) -0.1893(4) -0.2837(4) 0.0440(8) Uani 1 1 d . . . . .
H21A H -0.561270 -0.141710 -0.198466 0.053 Uiso 1 1 calc R . . . .
H21B H -0.575252 -0.284839 -0.268657 0.053 Uiso 1 1 calc R . . . .
C22 C -0.65015(17) -0.1602(4) -0.2759(5) 0.0501(10) Uani 1 1 d . . . . .
H22A H -0.671188 -0.212625 -0.355008 0.075 Uiso 1 1 calc GR . . . .
H22B H -0.657107 -0.066313 -0.295603 0.075 Uiso 1 1 calc GR . . . .
H22C H -0.665422 -0.183189 -0.171983 0.075 Uiso 1 1 calc GR . . . .


_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 Cl1 2.1959(7) . ?
Ni1 N1 1.947(2) . ?
Ni1 N2 1.869(2) . ?
Ni1 C16 1.879(3) . ?
N1 C1 1.321(4) . ?
N1 C9 1.368(4) . ?
N2 C8 1.402(3) . ?
N2 C10 1.381(4) . ?
N3 C11 1.425(4) . ?
N3 C16 1.364(4) . ?
N3 C17 1.386(4) . ?
N4 C16 1.362(4) . ?
N4 C18 1.387(4) . ?
N4 C19 1.466(4) . ?
C1 C2 1.414(4) . ?
C2 C3 1.357(5) . ?
C3 C4 1.409(5) . ?
C4 C5 1.410(5) . ?
C4 C9 1.424(4) . ?
C5 C6 1.367(5) . ?
C6 C7 1.418(4) . ?
C7 C8 1.386(4) . ?
C8 C9 1.404(4) . ?
C10 C11 1.405(4) . ?
C10 C15 1.412(4) . ?
C11 C12 1.396(4) . ?
C12 C13 1.386(5) . ?
C13 C14 1.401(5) . ?
C14 C15 1.380(4) . ?
C17 C18 1.327(5) . ?
C19 C20 1.517(5) . ?
C20 C21 1.519(5) . ?
C21 C22 1.541(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 Cl1 93.22(8) . . ?
N2 Ni1 Cl1 168.31(8) . . ?
N2 Ni1 N1 84.51(10) . . ?
N2 Ni1 C16 88.75(11) . . ?
C16 Ni1 Cl1 95.78(8) . . ?
C16 Ni1 N1 165.95(11) . . ?
C1 N1 Ni1 129.5(2) . . ?
C1 N1 C9 119.0(2) . . ?
C9 N1 Ni1 111.09(19) . . ?
C8 N2 Ni1 112.81(19) . . ?
C10 N2 Ni1 121.77(18) . . ?
C10 N2 C8 120.5(2) . . ?
C16 N3 C11 124.9(2) . . ?
C16 N3 C17 110.9(2) . . ?
C17 N3 C11 124.2(2) . . ?
C16 N4 C18 110.1(2) . . ?
C16 N4 C19 128.4(2) . . ?
C18 N4 C19 121.4(3) . . ?
N1 C1 C2 121.7(3) . . ?
C3 C2 C1 120.1(3) . . ?
C2 C3 C4 120.2(3) . . ?
C3 C4 C5 125.6(3) . . ?
C3 C4 C9 116.4(3) . . ?
C5 C4 C9 118.0(3) . . ?
C6 C5 C4 119.8(3) . . ?
C5 C6 C7 122.0(3) . . ?
C8 C7 C6 119.6(3) . . ?
N2 C8 C9 114.1(3) . . ?
C7 C8 N2 127.2(3) . . ?
C7 C8 C9 118.6(3) . . ?
N1 C9 C4 122.6(3) . . ?
N1 C9 C8 115.5(2) . . ?
C8 C9 C4 121.9(3) . . ?
N2 C10 C11 120.1(2) . . ?
N2 C10 C15 123.4(3) . . ?
C11 C10 C15 116.3(3) . . ?
C10 C11 N3 118.9(2) . . ?
C12 C11 N3 119.0(3) . . ?
C12 C11 C10 122.1(3) . . ?
C13 C12 C11 120.2(3) . . ?
C12 C13 C14 118.8(3) . . ?
C15 C14 C13 120.8(3) . . ?
C14 C15 C10 121.7(3) . . ?
N3 C16 Ni1 123.88(19) . . ?
N4 C16 Ni1 131.6(2) . . ?
N4 C16 N3 104.3(2) . . ?
C18 C17 N3 106.6(3) . . ?
C17 C18 N4 108.0(3) . . ?
N4 C19 C20 112.5(3) . . ?
C19 C20 C21 115.3(3) . . ?
C20 C21 C22 110.9(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_complex5a
_database_code_depnum_ccdc_archive 'CCDC 2211202'
loop_
_audit_author_name
_audit_author_address
li
;shandong university
China
;
_audit_update_record             
;
2023-05-22 deposited with the CCDC.	2023-05-24 downloaded from the CCDC.
;
_audit_creation_date             2023-05-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H27 Br0.106 Cl0.894 N4 Ni'
_chemical_formula_sum            'C23 H27 Br0.11 Cl0.89 N4 Ni'
_chemical_formula_weight         458.42
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.3434(2)
_cell_length_b                   14.2256(4)
_cell_length_c                   17.7157(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2102.67(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2755
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      30.7650
_cell_measurement_theta_min      2.7890
_shelx_estimated_absorpt_T_max   0.832
_shelx_estimated_absorpt_T_min   0.791
_exptl_absorpt_coefficient_mu    2.735
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_av_unetI/netI     0.0789
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7023
_diffrn_reflns_point_group_measured_fraction_full 0.908
_diffrn_reflns_point_group_measured_fraction_max 0.829
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.339
_diffrn_reflns_theta_min         3.985
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.574
_reflns_Friedel_fraction_full    0.805
_reflns_Friedel_fraction_max     0.703
_reflns_number_gt                3202
_reflns_number_total             3670
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 
;
 Flack x determined using 1090 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3670
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0401
_refine_ls_restrained_S_all      0.987
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0365P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.0971
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{Cl1, Br1}
3. Uiso/Uaniso restraints and constraints
Uanis(Cl1) = Uanis(Br1)
4. Others
 Sof(Br1)=1-FVAR(1)
 Sof(Cl1)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C4(H4A,H4B), C21(H21A,H21B), C2(H2A,H2B), C3(H3A,H3B),
 C22(H22A,H22B), C23(H23A,H23B)
5.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C18(H18), C17(H17), C6(H6), C15(H15), C16(H16), C11(H11), C9(H9),
 C10(H10), C5(H5)
5.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
Ni Ni 0.29985(8) 0.59323(5) 0.32290(4) 0.0211(2) Uani 1 1 d . . . . .
Cl1 Cl 0.46165(10) 0.67640(8) 0.24974(6) 0.0324(4) Uani 0.894(5) 1 d . . P A 1
N4 N 0.4690(4) 0.4990(3) 0.3530(2) 0.0215(7) Uani 1 1 d . . . . .
N2 N 0.0034(4) 0.6892(3) 0.3498(2) 0.0256(8) Uani 1 1 d . . . . .
N3 N 0.1815(4) 0.5380(3) 0.4002(2) 0.0222(8) Uani 1 1 d . . . . .
N1 N 0.0550(5) 0.6890(3) 0.2310(2) 0.0277(8) Uani 1 1 d . . . . .
C13 C 0.1016(4) 0.5924(3) 0.4528(2) 0.0219(8) Uani 1 1 d . . . . .
C19 C 0.3797(5) 0.4204(3) 0.3872(2) 0.0212(9) Uani 1 1 d . . . . .
C14 C 0.2307(5) 0.4470(3) 0.4171(2) 0.0212(9) Uani 1 1 d . . . . .
C12 C 0.1055(5) 0.5762(4) 0.5317(3) 0.0278(10) Uani 1 1 d . . . . .
H12 H 0.166552 0.524914 0.550501 0.033 Uiso 1 1 calc R U . . .
C20 C 0.5657(5) 0.5469(3) 0.4149(3) 0.0279(10) Uani 1 1 d . . . . .
H20A H 0.599926 0.610545 0.398992 0.033 Uiso 1 1 calc R U . . .
H20B H 0.502298 0.552199 0.461938 0.033 Uiso 1 1 calc R U . . .
C18 C 0.4343(5) 0.3290(3) 0.3921(3) 0.0264(9) Uani 1 1 d . . . . .
H18 H 0.533939 0.311660 0.370178 0.032 Uiso 1 1 calc R U . . .
C17 C 0.3405(5) 0.2621(3) 0.4298(3) 0.0275(10) Uani 1 1 d . . . . .
H17 H 0.375779 0.198747 0.433184 0.033 Uiso 1 1 calc R U . . .
C7 C 0.1168(5) 0.6631(3) 0.2985(2) 0.0235(9) Uani 1 1 d . . . . .
C8 C 0.0139(5) 0.6718(3) 0.4290(3) 0.0228(9) Uani 1 1 d . . . . .
C4 C 0.1151(6) 0.6627(4) 0.1561(3) 0.0303(10) Uani 1 1 d . . . . .
H4A H 0.226861 0.640123 0.160616 0.036 Uiso 1 1 calc R U . . .
H4B H 0.115186 0.718805 0.122993 0.036 Uiso 1 1 calc R U . . .
C6 C -0.1256(5) 0.7322(3) 0.3140(3) 0.0313(10) Uani 1 1 d . . . . .
H6 H -0.218352 0.757456 0.337618 0.038 Uiso 1 1 calc R U . . .
C15 C 0.1402(5) 0.3793(3) 0.4558(3) 0.0266(10) Uani 1 1 d . . . . .
H15 H 0.040103 0.395909 0.477592 0.032 Uiso 1 1 calc R U . . .
C16 C 0.1970(6) 0.2884(3) 0.4620(3) 0.0286(10) Uani 1 1 d . . . . .
H16 H 0.135892 0.243146 0.488953 0.034 Uiso 1 1 calc R U . . .
C11 C 0.0233(6) 0.6324(4) 0.5821(3) 0.0325(10) Uani 1 1 d . . . . .
H11 H 0.026654 0.618730 0.634574 0.039 Uiso 1 1 calc R U . . .
C9 C -0.0686(6) 0.7286(4) 0.4794(3) 0.0317(11) Uani 1 1 d . . . . .
H9 H -0.127865 0.780914 0.461229 0.038 Uiso 1 1 calc R U . . .
C21 C 0.7096(6) 0.4831(4) 0.4263(3) 0.0366(12) Uani 1 1 d . . . . .
H21A H 0.681957 0.428528 0.458390 0.044 Uiso 1 1 calc R U . . .
H21B H 0.799987 0.517644 0.449562 0.044 Uiso 1 1 calc R U . . .
C2 C 0.0097(6) 0.4941(4) 0.1648(3) 0.0381(12) Uani 1 1 d . . . . .
H2A H 0.114479 0.462245 0.158944 0.046 Uiso 1 1 calc R U . . .
H2B H -0.005024 0.508491 0.219024 0.046 Uiso 1 1 calc R U . . .
C10 C -0.0651(6) 0.7095(4) 0.5558(3) 0.0359(12) Uani 1 1 d . . . . .
H10 H -0.122005 0.748319 0.590250 0.043 Uiso 1 1 calc R U . . .
C3 C 0.0120(6) 0.5858(4) 0.1203(3) 0.0331(11) Uani 1 1 d . . . . .
H3A H -0.099219 0.609324 0.115386 0.040 Uiso 1 1 calc R U . . .
H3B H 0.052679 0.572953 0.068798 0.040 Uiso 1 1 calc R U . . .
C5 C -0.0943(6) 0.7310(4) 0.2406(3) 0.0343(11) Uani 1 1 d . . . . .
H5 H -0.161450 0.754595 0.201652 0.041 Uiso 1 1 calc R U . . .
C22 C 0.7506(6) 0.4521(4) 0.3460(4) 0.0447(15) Uani 1 1 d . . . . .
H22A H 0.782649 0.385135 0.345234 0.054 Uiso 1 1 calc R U . . .
H22B H 0.839517 0.490398 0.325458 0.054 Uiso 1 1 calc R U . . .
C1 C -0.1215(7) 0.4283(4) 0.1395(3) 0.0449(14) Uani 1 1 d . . . . .
H1A H -0.103959 0.410743 0.086687 0.067 Uiso 1 1 calc R U . . .
H1B H -0.225509 0.459802 0.144404 0.067 Uiso 1 1 calc R U . . .
H1C H -0.120412 0.371748 0.171066 0.067 Uiso 1 1 calc R U . . .
C23 C 0.5955(6) 0.4673(4) 0.2994(3) 0.0346(12) Uani 1 1 d . . . . .
H23A H 0.613441 0.515531 0.259935 0.042 Uiso 1 1 calc R U . . .
H23B H 0.562983 0.407996 0.274513 0.042 Uiso 1 1 calc R U . . .
Br1 Br 0.46165(10) 0.67640(8) 0.24974(6) 0.0324(4) Uani 0.106(5) 1 d . . P A 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
Ni Cl1 2.2140(12) . y
Ni N4 2.018(4) . y
Ni N3 1.863(4) . y
Ni C7 1.872(5) . y
Ni Br1 2.2140(12) . y
N4 C19 1.474(6) . ?
N4 C20 1.523(6) . ?
N4 C23 1.491(6) . ?
N2 C7 1.363(6) . ?
N2 C8 1.426(6) . ?
N2 C6 1.391(6) . ?
N3 C13 1.383(6) . ?
N3 C14 1.390(6) . ?
N1 C7 1.353(6) . ?
N1 C4 1.468(6) . ?
N1 C5 1.392(6) . ?
C13 C12 1.416(6) . ?
C13 C8 1.410(6) . ?
C19 C14 1.403(6) . ?
C19 C18 1.381(7) . ?
C14 C15 1.403(6) . ?
C12 H12 0.9500 . ?
C12 C11 1.381(7) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.518(7) . ?
C18 H18 0.9500 . ?
C18 C17 1.402(7) . ?
C17 H17 0.9500 . ?
C17 C16 1.378(7) . ?
C8 C9 1.387(7) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C3 1.529(7) . ?
C6 H6 0.9500 . ?
C6 C5 1.327(8) . ?
C15 H15 0.9500 . ?
C15 C16 1.382(7) . ?
C16 H16 0.9500 . ?
C11 H11 0.9500 . ?
C11 C10 1.402(8) . ?
C9 H9 0.9500 . ?
C9 C10 1.381(8) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.527(9) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.525(7) . ?
C2 C1 1.508(8) . ?
C10 H10 0.9500 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 H5 0.9500 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.551(8) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?

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
N4 Ni Cl1 94.77(11) . . y
N4 Ni Br1 94.77(11) . . y
N3 Ni Cl1 168.30(13) . . y
N3 Ni N4 84.03(15) . . y
N3 Ni C7 87.77(18) . . y
N3 Ni Br1 168.30(13) . . y
C7 Ni Cl1 94.53(14) . . y
C7 Ni N4 169.65(17) . . y
C7 Ni Br1 94.53(14) . . y
C19 N4 Ni 105.0(3) . . ?
C19 N4 C20 108.1(3) . . ?
C19 N4 C23 113.0(4) . . ?
C20 N4 Ni 105.3(3) . . ?
C23 N4 Ni 121.9(3) . . ?
C23 N4 C20 102.6(3) . . ?
C7 N2 C8 124.4(4) . . ?
C7 N2 C6 110.7(4) . . ?
C6 N2 C8 124.9(4) . . ?
C13 N3 Ni 121.0(3) . . ?
C13 N3 C14 121.3(4) . . ?
C14 N3 Ni 113.2(3) . . ?
C7 N1 C4 126.9(4) . . ?
C7 N1 C5 110.5(4) . . ?
C5 N1 C4 121.7(4) . . ?
N3 C13 C12 124.2(4) . . ?
N3 C13 C8 119.8(4) . . ?
C8 C13 C12 116.0(4) . . ?
C14 C19 N4 113.5(4) . . ?
C18 C19 N4 125.0(4) . . ?
C18 C19 C14 121.5(4) . . ?
N3 C14 C19 115.6(4) . . ?
N3 C14 C15 125.8(4) . . ?
C15 C14 C19 118.4(4) . . ?
C13 C12 H12 118.9 . . ?
C11 C12 C13 122.1(5) . . ?
C11 C12 H12 118.9 . . ?
N4 C20 H20A 110.9 . . ?
N4 C20 H20B 110.9 . . ?
H20A C20 H20B 108.9 . . ?
C21 C20 N4 104.3(4) . . ?
C21 C20 H20A 110.9 . . ?
C21 C20 H20B 110.9 . . ?
C19 C18 H18 120.5 . . ?
C19 C18 C17 119.0(4) . . ?
C17 C18 H18 120.5 . . ?
C18 C17 H17 120.1 . . ?
C16 C17 C18 119.9(4) . . ?
C16 C17 H17 120.1 . . ?
N2 C7 Ni 123.8(3) . . ?
N1 C7 Ni 131.2(3) . . ?
N1 C7 N2 104.5(4) . . ?
C13 C8 N2 117.8(4) . . ?
C9 C8 N2 120.1(4) . . ?
C9 C8 C13 122.0(4) . . ?
N1 C4 H4A 109.3 . . ?
N1 C4 H4B 109.3 . . ?
N1 C4 C3 111.4(4) . . ?
H4A C4 H4B 108.0 . . ?
C3 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
N2 C6 H6 126.6 . . ?
C5 C6 N2 106.8(4) . . ?
C5 C6 H6 126.6 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.8(4) . . ?
C16 C15 H15 120.1 . . ?
C17 C16 C15 121.3(4) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C12 C11 H11 120.0 . . ?
C12 C11 C10 120.0(5) . . ?
C10 C11 H11 120.0 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.4(5) . . ?
C10 C9 H9 119.8 . . ?
C20 C21 H21A 111.1 . . ?
C20 C21 H21B 111.1 . . ?
C20 C21 C22 103.1(4) . . ?
H21A C21 H21B 109.1 . . ?
C22 C21 H21A 111.1 . . ?
C22 C21 H21B 111.1 . . ?
H2A C2 H2B 107.8 . . ?
C3 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C1 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
C1 C2 C3 112.7(4) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 C11 119.4(5) . . ?
C9 C10 H10 120.3 . . ?
C4 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
C2 C3 C4 113.9(4) . . ?
C2 C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
N1 C5 H5 126.2 . . ?
C6 C5 N1 107.5(4) . . ?
C6 C5 H5 126.2 . . ?
C21 C22 H22A 110.6 . . ?
C21 C22 H22B 110.6 . . ?
C21 C22 C23 105.6(4) . . ?
H22A C22 H22B 108.7 . . ?
C23 C22 H22A 110.6 . . ?
C23 C22 H22B 110.6 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N4 C23 C22 107.0(4) . . ?
N4 C23 H23A 110.3 . . ?
N4 C23 H23B 110.3 . . ?
C22 C23 H23A 110.3 . . ?
C22 C23 H23B 110.3 . . ?
H23A C23 H23B 108.6 . . ?

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
Ni N4 C19 C14 -25.1(4) . . . . ?
Ni N4 C19 C18 156.2(4) . . . . ?
Ni N4 C20 C21 -169.8(3) . . . . ?
Ni N4 C23 C22 144.7(3) . . . . ?
Ni N3 C13 C12 -134.1(4) . . . . ?
Ni N3 C13 C8 43.6(5) . . . . ?
Ni N3 C14 C19 14.2(5) . . . . ?
Ni N3 C14 C15 -160.8(4) . . . . ?
Cl1 Ni N3 C13 48.6(8) . . . . ?
Cl1 Ni N3 C14 -107.8(6) . . . . ?
Cl1 Ni C7 N2 -138.8(4) . . . . ?
Cl1 Ni C7 N1 49.9(4) . . . . ?
N4 Ni N3 C13 133.3(3) . . . . ?
N4 Ni N3 C14 -23.1(3) . . . . ?
N4 Ni C7 N2 67.3(11) . . . . ?
N4 Ni C7 N1 -104.0(10) . . . . ?
N4 C19 C14 N3 9.0(5) . . . . ?
N4 C19 C14 C15 -175.6(4) . . . . ?
N4 C19 C18 C17 176.6(4) . . . . ?
N4 C20 C21 C22 38.7(5) . . . . ?
N2 C8 C9 C10 177.0(4) . . . . ?
N2 C6 C5 N1 -1.0(6) . . . . ?
N3 Ni C7 N2 29.7(4) . . . . ?
N3 Ni C7 N1 -141.5(5) . . . . ?
N3 C13 C12 C11 -179.8(4) . . . . ?
N3 C13 C8 N2 3.8(6) . . . . ?
N3 C13 C8 C9 179.9(4) . . . . ?
N3 C14 C15 C16 173.3(4) . . . . ?
N1 C4 C3 C2 -61.8(5) . . . . ?
C13 N3 C14 C19 -142.1(4) . . . . ?
C13 N3 C14 C15 42.9(6) . . . . ?
C13 C12 C11 C10 -1.3(7) . . . . ?
C13 C8 C9 C10 1.0(7) . . . . ?
C19 N4 C20 C21 78.4(4) . . . . ?
C19 N4 C23 C22 -88.8(5) . . . . ?
C19 C14 C15 C16 -1.5(6) . . . . ?
C19 C18 C17 C16 -0.7(7) . . . . ?
C14 N3 C13 C12 20.4(6) . . . . ?
C14 N3 C13 C8 -161.9(4) . . . . ?
C14 C19 C18 C17 -2.0(6) . . . . ?
C14 C15 C16 C17 -1.0(7) . . . . ?
C12 C13 C8 N2 -178.3(4) . . . . ?
C12 C13 C8 C9 -2.3(6) . . . . ?
C12 C11 C10 C9 -0.1(7) . . . . ?
C20 N4 C19 C14 87.0(4) . . . . ?
C20 N4 C19 C18 -91.7(5) . . . . ?
C20 N4 C23 C22 27.4(5) . . . . ?
C20 C21 C22 C23 -21.2(6) . . . . ?
C18 C19 C14 N3 -172.3(4) . . . . ?
C18 C19 C14 C15 3.1(6) . . . . ?
C18 C17 C16 C15 2.2(7) . . . . ?
C7 Ni N3 C13 -53.1(3) . . . . ?
C7 Ni N3 C14 150.6(3) . . . . ?
C7 N2 C8 C13 -28.5(6) . . . . ?
C7 N2 C8 C9 155.4(4) . . . . ?
C7 N2 C6 C5 1.2(6) . . . . ?
C7 N1 C4 C3 102.9(5) . . . . ?
C7 N1 C5 C6 0.5(6) . . . . ?
C8 N2 C7 Ni 3.8(6) . . . . ?
C8 N2 C7 N1 177.0(4) . . . . ?
C8 N2 C6 C5 -176.7(4) . . . . ?
C8 C13 C12 C11 2.4(6) . . . . ?
C8 C9 C10 C11 0.3(7) . . . . ?
C4 N1 C7 Ni 3.9(7) . . . . ?
C4 N1 C7 N2 -168.6(4) . . . . ?
C4 N1 C5 C6 170.0(4) . . . . ?
C6 N2 C7 Ni -174.1(3) . . . . ?
C6 N2 C7 N1 -0.9(5) . . . . ?
C6 N2 C8 C13 149.2(4) . . . . ?
C6 N2 C8 C9 -26.9(6) . . . . ?
C21 C22 C23 N4 -4.0(6) . . . . ?
C5 N1 C7 Ni 172.8(4) . . . . ?
C5 N1 C7 N2 0.3(5) . . . . ?
C5 N1 C4 C3 -64.8(6) . . . . ?
C1 C2 C3 C4 166.1(4) . . . . ?
C23 N4 C19 C14 -160.1(4) . . . . ?
C23 N4 C19 C18 21.2(6) . . . . ?
C23 N4 C20 C21 -41.3(5) . . . . ?
Br1 Ni N3 C13 48.6(8) . . . . ?
Br1 Ni N3 C14 -107.8(6) . . . . ?
Br1 Ni C7 N2 -138.8(4) . . . . ?
Br1 Ni C7 N1 49.9(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_complex3b
_database_code_depnum_ccdc_archive 'CCDC 1865452'
loop_
_audit_author_name
_audit_author_address
li
;shandong university
China
;
_audit_update_record             
;
2023-05-22 deposited with the CCDC.	2023-05-24 downloaded from the CCDC.
;
_audit_creation_date             2023-05-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H15 Br0.075 Cl0.968 N4 Ni0.96'
_chemical_formula_sum            'C19 H15 Br0.08 Cl0.95 N4 Ni0.96'
_chemical_formula_weight         395.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 '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 -0.9338 1.0006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -1.3357 3.2904 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   7.8582(3)
_cell_length_b                   24.1174(12)
_cell_length_c                   17.5914(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.976(3)
_cell_angle_gamma                90
_cell_volume                     3315.8(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    36386
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      64.42
_cell_measurement_theta_min      1.91
_shelx_estimated_absorpt_T_max   0.354
_shelx_estimated_absorpt_T_min   0.310
_exptl_absorpt_coefficient_mu    7.273
_exptl_absorpt_correction_T_max  0.1638
_exptl_absorpt_correction_T_min  0.1081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Afterwards a spherical absorption correction was performed within STOE LANA.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1621
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16325
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        53.597
_diffrn_reflns_theta_max         57.513
_diffrn_reflns_theta_min         2.715
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       ?
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34143
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5665
_reflns_number_total             6666
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         1.251
_refine_diff_density_min         -0.904
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     457
_refine_ls_number_reflns         6666
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0546
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1163P)²+0.0829P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1474
_refine_ls_wR_factor_ref         0.1545
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{Cl2, Br2}
{Cl1, Br1}
3. Uiso/Uaniso restraints and constraints
Uanis(Cl2) = Uanis(Br2)
Uanis(Cl1) = Uanis(Br1)
4. Others
 Sof(Br2)=Sof(Br1)=1-FVAR(1)
 Sof(Cl2)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C24(H24), C25(H25),
  C26(H26), C31(H31), C32(H32), C33(H33), C34(H34), C36(H36), C37(H37)
5.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C38(H38A,H38B,H38C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.13055(5) 0.78598(2) 0.28986(2) 0.03004(17) Uani 0.960(3) 1 d . . . . .
Cl1 Cl 0.25866(10) 0.76988(3) 0.40820(4) 0.0459(4) Uani 0.968(7) 1 d . . . A 3
N1 N 0.0705(3) 0.70874(10) 0.26715(15) 0.0363(6) Uani 1 1 d . . . . .
N2 N 0.0700(3) 0.79676(10) 0.18517(14) 0.0335(5) Uani 1 1 d . . . . .
N3 N 0.1750(3) 0.89898(10) 0.24753(13) 0.0312(5) Uani 1 1 d . . . . .
N4 N 0.0760(3) 0.89568(11) 0.35682(14) 0.0358(6) Uani 1 1 d . . . . .
C1 C 0.0837(4) 0.66451(13) 0.3130(2) 0.0446(8) Uani 1 1 d . . . . .
H1 H 0.143138 0.667671 0.362634 0.053 Uiso 1 1 calc R U . . .
C2 C 0.0113(5) 0.61331(14) 0.2890(2) 0.0523(9) Uani 1 1 d . . . . .
H2 H 0.023499 0.582254 0.322313 0.063 Uiso 1 1 calc R U . . .
C3 C -0.0756(5) 0.60789(14) 0.2189(2) 0.0507(9) Uani 1 1 d . . . . .
H3 H -0.124964 0.573219 0.203402 0.061 Uiso 1 1 calc R U . . .
C4 C -0.0929(4) 0.65394(13) 0.1686(2) 0.0431(8) Uani 1 1 d . . . . .
C5 C -0.1826(5) 0.65350(14) 0.0948(2) 0.0482(8) Uani 1 1 d . . . . .
H5 H -0.235039 0.620373 0.074736 0.058 Uiso 1 1 calc R U . . .
C6 C -0.1935(4) 0.70112(15) 0.0524(2) 0.0475(8) Uani 1 1 d . . . . .
H6 H -0.258423 0.700881 0.003748 0.057 Uiso 1 1 calc R U . . .
C7 C -0.1114(4) 0.75060(14) 0.07857(18) 0.0419(7) Uani 1 1 d . . . . .
H7 H -0.120053 0.782772 0.047253 0.050 Uiso 1 1 calc R U . . .
C8 C -0.0183(4) 0.75234(12) 0.14991(17) 0.0344(6) Uani 1 1 d . . . . .
C9 C -0.0145(4) 0.70366(12) 0.19608(18) 0.0363(7) Uani 1 1 d . . . . .
C10 C 0.1675(4) 0.83187(11) 0.14367(16) 0.0314(6) Uani 1 1 d . . . . .
C11 C 0.2260(3) 0.88258(12) 0.17567(16) 0.0308(6) Uani 1 1 d . . . . .
C12 C 0.3301(4) 0.91797(12) 0.13886(16) 0.0336(6) Uani 1 1 d . . . . .
H12 H 0.366969 0.952108 0.161983 0.040 Uiso 1 1 calc R U . . .
C13 C 0.3802(4) 0.90333(13) 0.06812(17) 0.0380(7) Uani 1 1 d . . . . .
H13 H 0.452877 0.927081 0.042986 0.046 Uiso 1 1 calc R U . . .
C14 C 0.3232(4) 0.85375(13) 0.03447(17) 0.0370(7) Uani 1 1 d . . . . .
H14 H 0.357166 0.843486 -0.013865 0.044 Uiso 1 1 calc R U . . .
C15 C 0.2167(4) 0.81904(12) 0.07123(16) 0.0340(6) Uani 1 1 d . . . . .
H15 H 0.176192 0.785780 0.046711 0.041 Uiso 1 1 calc R U . . .
C16 C 0.1302(4) 0.86291(13) 0.30126(16) 0.0324(6) Uani 1 1 d . . . . .
C17 C 0.1513(4) 0.95320(13) 0.26963(18) 0.0381(7) Uani 1 1 d . . . . .
H17 H 0.173912 0.985741 0.241944 0.046 Uiso 1 1 calc R U . . .
C18 C 0.0896(4) 0.95072(13) 0.33849(18) 0.0393(7) Uani 1 1 d . . . . .
H18 H 0.060982 0.981377 0.368603 0.047 Uiso 1 1 calc R U . . .
C19 C 0.0020(4) 0.87711(14) 0.42530(17) 0.0420(7) Uani 1 1 d . . . . .
H19A H -0.060356 0.842357 0.414311 0.063 Uiso 1 1 calc R U . . .
H19B H -0.076822 0.905434 0.440822 0.063 Uiso 1 1 calc R U . . .
H19C H 0.093648 0.871080 0.466684 0.063 Uiso 1 1 calc R U . . .
Ni2 Ni 0.34700(5) 0.52373(2) 0.17841(2) 0.03337(18) Uani 0.963(3) 1 d . . . . .
Cl2 Cl 0.22693(10) 0.52167(4) 0.05853(4) 0.0515(3) Uani 0.925(3) 1 d . . P B 1
N5 N 0.3847(3) 0.60322(11) 0.18034(17) 0.0436(7) Uani 1 1 d . . . . .
N6 N 0.4094(3) 0.52807(10) 0.28374(14) 0.0351(6) Uani 1 1 d . . . . .
N7 N 0.3193(3) 0.41846(10) 0.24945(13) 0.0322(5) Uani 1 1 d . . . . .
N8 N 0.4259(3) 0.40796(11) 0.14271(14) 0.0381(6) Uani 1 1 d . . . . .
C20 C 0.3564(5) 0.64015(16) 0.1237(3) 0.0573(10) Uani 1 1 d . . . . .
H20 H 0.296151 0.628897 0.076641 0.069 Uiso 1 1 calc R U . . .
C21 C 0.4132(6) 0.69470(17) 0.1322(3) 0.0682(13) Uani 1 1 d . . . . .
H21 H 0.391582 0.720142 0.091112 0.082 Uiso 1 1 calc R U . . .
C22 C 0.4993(6) 0.71162(16) 0.1991(3) 0.0719(15) Uani 1 1 d . . . . .
H22 H 0.536883 0.748954 0.205066 0.086 Uiso 1 1 calc R U . . .
C23 C 0.5331(5) 0.67338(14) 0.2602(3) 0.0550(10) Uani 1 1 d . . . . .
C24 C 0.6262(5) 0.68539(16) 0.3318(3) 0.0628(12) Uani 1 1 d . . . . .
H24 H 0.672026 0.721433 0.341727 0.075 Uiso 1 1 calc R U . . .
C25 C 0.6500(5) 0.64511(16) 0.3865(3) 0.0589(10) Uani 1 1 d . . . . .
H25 H 0.714139 0.653513 0.433885 0.071 Uiso 1 1 calc R U . . .
C26 C 0.5818(4) 0.59141(14) 0.3744(2) 0.0453(8) Uani 1 1 d . . . . .
H26 H 0.600743 0.564100 0.413298 0.054 Uiso 1 1 calc R U . . .
C27 C 0.4877(4) 0.57850(13) 0.30631(19) 0.0397(7) Uani 1 1 d . . . . .
C28 C 0.4696(4) 0.61983(13) 0.2481(2) 0.0439(8) Uani 1 1 d . . . . .
C29 C 0.3216(4) 0.49797(12) 0.33487(16) 0.0327(6) Uani 1 1 d . . . . .
C30 C 0.2693(3) 0.44327(12) 0.31707(16) 0.0312(6) Uani 1 1 d . . . . .
C31 C 0.1781(4) 0.41210(13) 0.36524(16) 0.0347(6) Uani 1 1 d . . . . .
H31 H 0.144340 0.375350 0.351311 0.042 Uiso 1 1 calc R U . . .
C32 C 0.1357(4) 0.43419(14) 0.43365(18) 0.0408(7) Uani 1 1 d . . . . .
H32 H 0.073430 0.412875 0.466781 0.049 Uiso 1 1 calc R U . . .
C33 C 0.1857(4) 0.48773(14) 0.45263(18) 0.0409(7) Uani 1 1 d . . . . .
H33 H 0.158308 0.503212 0.499498 0.049 Uiso 1 1 calc R U . . .
C34 C 0.2751(4) 0.51916(13) 0.40437(18) 0.0363(7) Uani 1 1 d . . . . .
H34 H 0.306066 0.556108 0.418527 0.044 Uiso 1 1 calc R U . . .
C35 C 0.3629(4) 0.44678(13) 0.18779(16) 0.0334(6) Uani 1 1 d . . . . .
C36 C 0.3532(4) 0.36236(13) 0.24183(18) 0.0378(7) Uani 1 1 d . . . . .
H36 H 0.332714 0.333839 0.277004 0.045 Uiso 1 1 calc R U . . .
C37 C 0.4200(4) 0.35616(14) 0.17553(19) 0.0412(7) Uani 1 1 d . . . . .
H37 H 0.456684 0.322338 0.154854 0.049 Uiso 1 1 calc R U . . .
C38 C 0.4985(5) 0.41814(16) 0.07077(18) 0.0491(8) Uani 1 1 d . . . . .
H38A H 0.406363 0.419263 0.028737 0.074 Uiso 1 1 calc R U . . .
H38B H 0.578553 0.388288 0.061651 0.074 Uiso 1 1 calc R U . . .
H38C H 0.559322 0.453673 0.073697 0.074 Uiso 1 1 calc R U . . .
Br2 Br 0.22693(10) 0.52167(4) 0.05853(4) 0.0515(3) Uani 0.075(3) 1 d . . P B 2
Br1 Br 0.25866(10) 0.76988(3) 0.40820(4) 0.046(2) Uani 0.075(3) 1 d . . P A 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 Cl1 2.2499(8) . y
Ni1 N1 1.953(3) . y
Ni1 N2 1.871(2) . y
Ni1 C16 1.866(3) . y
Ni1 Br1 2.2499(8) . y
N1 C1 1.334(4) . ?
N1 C9 1.360(4) . ?
N2 C8 1.387(4) . ?
N2 C10 1.398(3) . ?
N3 C11 1.421(3) . ?
N3 C16 1.358(4) . ?
N3 C17 1.382(4) . ?
N4 C16 1.359(4) . ?
N4 C18 1.373(4) . ?
N4 C19 1.461(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.406(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.351(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.418(5) . ?
C4 C5 1.411(5) . ?
C4 C9 1.410(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.367(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.410(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.386(5) . ?
C8 C9 1.426(4) . ?
C10 C11 1.403(4) . ?
C10 C15 1.404(4) . ?
C11 C12 1.388(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.389(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.388(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.390(4) . ?
C15 H15 0.9500 . ?
C17 H17 0.9500 . ?
C17 C18 1.352(4) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
Ni2 Cl2 2.2194(9) . y
Ni2 N5 1.939(3) . y
Ni2 N6 1.870(3) . y
Ni2 C35 1.866(3) . y
Ni2 Br2 2.2194(9) . y
N5 C20 1.337(4) . ?
N5 C28 1.364(5) . ?
N6 C27 1.401(4) . ?
N6 C29 1.393(4) . ?
N7 C30 1.423(3) . ?
N7 C35 1.356(4) . ?
N7 C36 1.388(4) . ?
N8 C35 1.353(4) . ?
N8 C37 1.379(4) . ?
N8 C38 1.462(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.392(6) . ?
C21 H21 0.9500 . ?
C21 C22 1.358(7) . ?
C22 H22 0.9500 . ?
C22 C23 1.420(6) . ?
C23 C24 1.419(6) . ?
C23 C28 1.393(5) . ?
C24 H24 0.9500 . ?
C24 C25 1.366(6) . ?
C25 H25 0.9500 . ?
C25 C26 1.409(5) . ?
C26 H26 0.9500 . ?
C26 C27 1.377(5) . ?
C27 C28 1.426(5) . ?
C29 C30 1.407(4) . ?
C29 C34 1.408(4) . ?
C30 C31 1.387(4) . ?
C31 H31 0.9500 . ?
C31 C32 1.388(4) . ?
C32 H32 0.9500 . ?
C32 C33 1.381(5) . ?
C33 H33 0.9500 . ?
C33 C34 1.383(4) . ?
C34 H34 0.9500 . ?
C36 H36 0.9500 . ?
C36 C37 1.336(4) . ?
C37 H37 0.9500 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?

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 Cl1 95.74(8) . . y
N1 Ni1 Br1 95.74(8) . . y
N2 Ni1 Cl1 167.91(8) . . y
N2 Ni1 N1 84.26(11) . . y
N2 Ni1 Br1 167.91(8) . . y
C16 Ni1 Cl1 94.45(9) . . y
C16 Ni1 N1 165.32(12) . . y
C16 Ni1 N2 87.97(11) . . y
C16 Ni1 Br1 94.45(9) . . y
C1 N1 Ni1 129.6(2) . . ?
C1 N1 C9 118.9(3) . . ?
C9 N1 Ni1 111.05(19) . . ?
C8 N2 Ni1 113.38(18) . . ?
C8 N2 C10 120.7(2) . . ?
C10 N2 Ni1 120.1(2) . . ?
C16 N3 C11 123.9(2) . . ?
C16 N3 C17 111.0(2) . . ?
C17 N3 C11 124.9(2) . . ?
C16 N4 C18 110.8(2) . . ?
C16 N4 C19 126.6(3) . . ?
C18 N4 C19 122.5(2) . . ?
N1 C1 H1 119.4 . . ?
N1 C1 C2 121.1(4) . . ?
C2 C1 H1 119.4 . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 125.1(3) . . ?
C9 C4 C3 116.2(3) . . ?
C9 C4 C5 118.7(3) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.5(3) . . ?
C6 C5 H5 120.3 . . ?
C5 C6 H6 118.9 . . ?
C5 C6 C7 122.2(3) . . ?
C7 C6 H6 118.9 . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 120.1(3) . . ?
C8 C7 H7 120.0 . . ?
N2 C8 C9 113.6(3) . . ?
C7 C8 N2 128.4(3) . . ?
C7 C8 C9 117.9(3) . . ?
N1 C9 C4 123.1(3) . . ?
N1 C9 C8 115.4(3) . . ?
C4 C9 C8 121.5(3) . . ?
N2 C10 C11 119.5(2) . . ?
N2 C10 C15 123.9(3) . . ?
C11 C10 C15 116.5(2) . . ?
C10 C11 N3 119.2(2) . . ?
C12 C11 N3 118.6(3) . . ?
C12 C11 C10 122.2(3) . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.8(3) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.5(3) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.2(3) . . ?
C15 C14 H14 119.9 . . ?
C10 C15 H15 119.1 . . ?
C14 C15 C10 121.7(3) . . ?
C14 C15 H15 119.1 . . ?
N3 C16 Ni1 124.0(2) . . ?
N3 C16 N4 104.6(3) . . ?
N4 C16 Ni1 131.3(2) . . ?
N3 C17 H17 126.8 . . ?
C18 C17 N3 106.3(3) . . ?
C18 C17 H17 126.8 . . ?
N4 C18 H18 126.4 . . ?
C17 C18 N4 107.3(3) . . ?
C17 C18 H18 126.4 . . ?
N4 C19 H19A 109.5 . . ?
N4 C19 H19B 109.5 . . ?
N4 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N5 Ni2 Cl2 95.04(9) . . y
N5 Ni2 Br2 95.04(9) . . y
N6 Ni2 Cl2 169.95(8) . . y
N6 Ni2 N5 84.46(12) . . y
N6 Ni2 Br2 169.95(8) . . y
C35 Ni2 Cl2 94.57(9) . . y
C35 Ni2 N5 166.56(13) . . y
C35 Ni2 N6 87.70(11) . . y
C35 Ni2 Br2 94.57(9) . . y
C20 N5 Ni2 129.2(3) . . ?
C20 N5 C28 118.9(3) . . ?
C28 N5 Ni2 111.4(2) . . ?
C27 N6 Ni2 113.0(2) . . ?
C29 N6 Ni2 120.9(2) . . ?
C29 N6 C27 120.1(2) . . ?
C35 N7 C30 124.9(2) . . ?
C35 N7 C36 110.3(2) . . ?
C36 N7 C30 124.3(2) . . ?
C35 N8 C37 110.6(3) . . ?
C35 N8 C38 126.2(3) . . ?
C37 N8 C38 123.2(3) . . ?
N5 C20 H20 119.2 . . ?
N5 C20 C21 121.5(5) . . ?
C21 C20 H20 119.2 . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.1(4) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 120.1 . . ?
C21 C22 C23 119.9(4) . . ?
C23 C22 H22 120.1 . . ?
C24 C23 C22 125.3(4) . . ?
C28 C23 C22 116.7(4) . . ?
C28 C23 C24 118.0(4) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 120.0(3) . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 119.2 . . ?
C24 C25 C26 121.7(4) . . ?
C26 C25 H25 119.2 . . ?
C25 C26 H26 120.0 . . ?
C27 C26 C25 120.0(4) . . ?
C27 C26 H26 120.0 . . ?
N6 C27 C28 113.3(3) . . ?
C26 C27 N6 128.5(3) . . ?
C26 C27 C28 118.1(3) . . ?
N5 C28 C23 122.8(3) . . ?
N5 C28 C27 115.2(3) . . ?
C23 C28 C27 122.0(4) . . ?
N6 C29 C30 119.8(2) . . ?
N6 C29 C34 124.2(3) . . ?
C30 C29 C34 115.9(3) . . ?
C29 C30 N7 118.7(2) . . ?
C31 C30 N7 119.2(3) . . ?
C31 C30 C29 122.0(3) . . ?
C30 C31 H31 119.7 . . ?
C30 C31 C32 120.5(3) . . ?
C32 C31 H31 119.7 . . ?
C31 C32 H32 120.6 . . ?
C33 C32 C31 118.7(3) . . ?
C33 C32 H32 120.6 . . ?
C32 C33 H33 119.5 . . ?
C32 C33 C34 120.9(3) . . ?
C34 C33 H33 119.5 . . ?
C29 C34 H34 119.1 . . ?
C33 C34 C29 121.9(3) . . ?
C33 C34 H34 119.1 . . ?
N7 C35 Ni2 123.5(2) . . ?
N8 C35 Ni2 131.4(2) . . ?
N8 C35 N7 105.0(3) . . ?
N7 C36 H36 126.6 . . ?
C37 C36 N7 106.9(3) . . ?
C37 C36 H36 126.6 . . ?
N8 C37 H37 126.4 . . ?
C36 C37 N8 107.3(3) . . ?
C36 C37 H37 126.4 . . ?
N8 C38 H38A 109.5 . . ?
N8 C38 H38B 109.5 . . ?
N8 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 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
Ni1 N1 C1 C2 170.9(2) . . . . ?
Ni1 N1 C9 C4 -171.3(2) . . . . ?
Ni1 N1 C9 C8 9.2(3) . . . . ?
Ni1 N2 C8 C7 165.4(2) . . . . ?
Ni1 N2 C8 C9 -12.1(3) . . . . ?
Ni1 N2 C10 C11 -42.0(3) . . . . ?
Ni1 N2 C10 C15 136.0(3) . . . . ?
Cl1 Ni1 N2 C8 104.3(4) . . . . ?
Cl1 Ni1 N2 C10 -48.9(5) . . . . ?
Cl1 Ni1 C16 N3 135.3(2) . . . . ?
Cl1 Ni1 C16 N4 -50.9(3) . . . . ?
N1 Ni1 N2 C8 13.7(2) . . . . ?
N1 Ni1 N2 C10 -139.6(2) . . . . ?
N1 Ni1 C16 N3 -90.8(5) . . . . ?
N1 Ni1 C16 N4 83.0(5) . . . . ?
N1 C1 C2 C3 -0.8(5) . . . . ?
N2 Ni1 C16 N3 -32.8(3) . . . . ?
N2 Ni1 C16 N4 140.9(3) . . . . ?
N2 C8 C9 N1 1.5(4) . . . . ?
N2 C8 C9 C4 -178.0(3) . . . . ?
N2 C10 C11 N3 -4.3(4) . . . . ?
N2 C10 C11 C12 176.8(3) . . . . ?
N2 C10 C15 C14 -175.7(3) . . . . ?
N3 C11 C12 C13 -179.2(3) . . . . ?
N3 C17 C18 N4 -0.3(4) . . . . ?
C1 N1 C9 C4 1.3(4) . . . . ?
C1 N1 C9 C8 -178.1(3) . . . . ?
C1 C2 C3 C4 0.6(5) . . . . ?
C2 C3 C4 C5 -179.0(3) . . . . ?
C2 C3 C4 C9 0.5(5) . . . . ?
C3 C4 C5 C6 178.5(3) . . . . ?
C3 C4 C9 N1 -1.5(4) . . . . ?
C3 C4 C9 C8 178.0(3) . . . . ?
C4 C5 C6 C7 2.8(5) . . . . ?
C5 C4 C9 N1 178.0(3) . . . . ?
C5 C4 C9 C8 -2.5(4) . . . . ?
C5 C6 C7 C8 -1.1(5) . . . . ?
C6 C7 C8 N2 -179.9(3) . . . . ?
C6 C7 C8 C9 -2.4(4) . . . . ?
C7 C8 C9 N1 -176.3(2) . . . . ?
C7 C8 C9 C4 4.2(4) . . . . ?
C8 N2 C10 C11 166.7(3) . . . . ?
C8 N2 C10 C15 -15.2(4) . . . . ?
C9 N1 C1 C2 -0.2(4) . . . . ?
C9 C4 C5 C6 -1.0(4) . . . . ?
C10 N2 C8 C7 -41.5(4) . . . . ?
C10 N2 C8 C9 140.9(3) . . . . ?
C10 C11 C12 C13 -0.3(4) . . . . ?
C11 N3 C16 Ni1 0.7(4) . . . . ?
C11 N3 C16 N4 -174.5(2) . . . . ?
C11 N3 C17 C18 174.9(3) . . . . ?
C11 C10 C15 C14 2.4(4) . . . . ?
C11 C12 C13 C14 1.0(4) . . . . ?
C12 C13 C14 C15 0.1(5) . . . . ?
C13 C14 C15 C10 -1.8(5) . . . . ?
C15 C10 C11 N3 177.5(3) . . . . ?
C15 C10 C11 C12 -1.3(4) . . . . ?
C16 Ni1 N2 C8 -153.9(2) . . . . ?
C16 Ni1 N2 C10 52.9(2) . . . . ?
C16 N3 C11 C10 26.2(4) . . . . ?
C16 N3 C11 C12 -154.9(3) . . . . ?
C16 N3 C17 C18 -0.3(4) . . . . ?
C16 N4 C18 C17 0.8(4) . . . . ?
C17 N3 C11 C10 -148.4(3) . . . . ?
C17 N3 C11 C12 30.5(4) . . . . ?
C17 N3 C16 Ni1 175.9(2) . . . . ?
C17 N3 C16 N4 0.8(3) . . . . ?
C18 N4 C16 Ni1 -175.6(2) . . . . ?
C18 N4 C16 N3 -1.0(3) . . . . ?
C19 N4 C16 Ni1 0.6(5) . . . . ?
C19 N4 C16 N3 175.3(3) . . . . ?
C19 N4 C18 C17 -175.6(3) . . . . ?
Ni2 N5 C20 C21 -170.8(3) . . . . ?
Ni2 N5 C28 C23 170.9(2) . . . . ?
Ni2 N5 C28 C27 -9.7(3) . . . . ?
Ni2 N6 C27 C26 -164.4(3) . . . . ?
Ni2 N6 C27 C28 12.9(3) . . . . ?
Ni2 N6 C29 C30 40.1(4) . . . . ?
Ni2 N6 C29 C34 -138.0(3) . . . . ?
Cl2 Ni2 N6 C27 -102.1(5) . . . . ?
Cl2 Ni2 N6 C29 50.8(6) . . . . ?
Cl2 Ni2 C35 N7 -134.9(2) . . . . ?
Cl2 Ni2 C35 N8 50.1(3) . . . . ?
N5 Ni2 N6 C27 -14.5(2) . . . . ?
N5 Ni2 N6 C29 138.4(2) . . . . ?
N5 Ni2 C35 N7 89.6(5) . . . . ?
N5 Ni2 C35 N8 -85.4(6) . . . . ?
N5 C20 C21 C22 -0.1(6) . . . . ?
N6 Ni2 C35 N7 35.3(2) . . . . ?
N6 Ni2 C35 N8 -139.7(3) . . . . ?
N6 C27 C28 N5 -1.8(4) . . . . ?
N6 C27 C28 C23 177.6(3) . . . . ?
N6 C29 C30 N7 4.8(4) . . . . ?
N6 C29 C30 C31 -178.5(3) . . . . ?
N6 C29 C34 C33 179.0(3) . . . . ?
N7 C30 C31 C32 176.4(3) . . . . ?
N7 C36 C37 N8 -0.4(4) . . . . ?
C20 N5 C28 C23 -2.1(5) . . . . ?
C20 N5 C28 C27 177.4(3) . . . . ?
C20 C21 C22 C23 0.7(6) . . . . ?
C21 C22 C23 C24 177.9(3) . . . . ?
C21 C22 C23 C28 -1.9(5) . . . . ?
C22 C23 C24 C25 179.7(3) . . . . ?
C22 C23 C28 N5 2.6(5) . . . . ?
C22 C23 C28 C27 -176.8(3) . . . . ?
C23 C24 C25 C26 -1.0(5) . . . . ?
C24 C23 C28 N5 -177.2(3) . . . . ?
C24 C23 C28 C27 3.5(5) . . . . ?
C24 C25 C26 C27 -0.4(5) . . . . ?
C25 C26 C27 N6 -179.7(3) . . . . ?
C25 C26 C27 C28 3.1(4) . . . . ?
C26 C27 C28 N5 175.8(3) . . . . ?
C26 C27 C28 C23 -4.8(5) . . . . ?
C27 N6 C29 C30 -168.9(3) . . . . ?
C27 N6 C29 C34 13.1(4) . . . . ?
C28 N5 C20 C21 0.7(5) . . . . ?
C28 C23 C24 C25 -0.5(5) . . . . ?
C29 N6 C27 C26 42.5(4) . . . . ?
C29 N6 C27 C28 -140.2(3) . . . . ?
C29 C30 C31 C32 -0.3(4) . . . . ?
C30 N7 C35 Ni2 -5.2(4) . . . . ?
C30 N7 C35 N8 170.9(3) . . . . ?
C30 N7 C36 C37 -171.0(3) . . . . ?
C30 C29 C34 C33 0.9(4) . . . . ?
C30 C31 C32 C33 0.1(5) . . . . ?
C31 C32 C33 C34 0.5(5) . . . . ?
C32 C33 C34 C29 -1.1(5) . . . . ?
C34 C29 C30 N7 -177.0(3) . . . . ?
C34 C29 C30 C31 -0.3(4) . . . . ?
C35 Ni2 N6 C27 154.6(2) . . . . ?
C35 Ni2 N6 C29 -52.5(2) . . . . ?
C35 N7 C30 C29 -23.2(4) . . . . ?
C35 N7 C30 C31 160.0(3) . . . . ?
C35 N7 C36 C37 0.8(4) . . . . ?
C35 N8 C37 C36 -0.1(4) . . . . ?
C36 N7 C30 C29 147.3(3) . . . . ?
C36 N7 C30 C31 -29.5(4) . . . . ?
C36 N7 C35 Ni2 -176.9(2) . . . . ?
C36 N7 C35 N8 -0.8(3) . . . . ?
C37 N8 C35 Ni2 176.2(2) . . . . ?
C37 N8 C35 N7 0.6(3) . . . . ?
C38 N8 C35 Ni2 -1.0(5) . . . . ?
C38 N8 C35 N7 -176.7(3) . . . . ?
C38 N8 C37 C36 177.3(3) . . . . ?
Br2 Ni2 N6 C27 -102.1(5) . . . . ?
Br2 Ni2 N6 C29 50.8(6) . . . . ?
Br2 Ni2 C35 N7 -134.9(2) . . . . ?
Br2 Ni2 C35 N8 50.1(3) . . . . ?
Br1 Ni1 N2 C8 104.3(4) . . . . ?
Br1 Ni1 N2 C10 -48.9(5) . . . . ?
Br1 Ni1 C16 N3 135.3(2) . . . . ?
Br1 Ni1 C16 N4 -50.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
