# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_tx12874_auto
_database_code_depnum_ccdc_archive 'CCDC 2266355'
loop_
_audit_author_name
_audit_author_address
'Xiaofang Li'
;HUNAN university of science and technology
China
;
_audit_update_record             
;
2023-05-30 deposited with the CCDC.	2023-07-21 downloaded from the CCDC.
;
_audit_creation_date             2023-05-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C42 H28 Br7 N5 Ni'
_chemical_formula_sum            'C42 H28 Br7 N5 Ni'
_chemical_formula_weight         1220.77
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Ni CNBrH'
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'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.4650(2)
_cell_length_b                   20.4051(2)
_cell_length_c                   22.2551(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.1580(10)
_cell_angle_gamma                90
_cell_volume                     5511.96(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    24634
_cell_measurement_temperature    169.98(10)
_cell_measurement_theta_max      75.5060
_cell_measurement_theta_min      2.9590
_shelx_estimated_absorpt_T_max   0.731
_shelx_estimated_absorpt_T_min   0.349
_exptl_absorpt_coefficient_mu    6.678
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2352
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            41879
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.626
_diffrn_reflns_theta_min         4.333
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -80.00 -47.00   0.50    0.08    -- -103.25  77.00 -60.00   66
  2  ω    -85.00 -31.00   0.50    0.08    -- -103.25  77.00 -30.00  108
  3  ω    -61.00 -32.00   0.50    0.08    -- -103.25  57.00 -60.00   58
  4  ω    -62.00 -32.00   0.50    0.08    -- -103.25  57.00 -30.00   60
  5  ω    -13.00  23.00   0.50    0.05    --  -48.81  19.00  60.00   72
  6  ω    -40.00  19.00   0.50    0.05    --  -48.81  38.00  90.00  118
  7  ω    -59.00 -33.00   0.50    0.08    -- -103.25  57.00 120.00   52
  8  ω    -62.00 -34.00   0.50    0.08    -- -103.25  57.00 150.00   56
  9  ω   -117.00 -66.00   0.50    0.05    --  -48.81 -57.00 150.00  102
 10  ω   -146.00 -97.00   0.50    0.08    -- -103.25-107.00-135.00   98
 11  ω   -106.00 -46.00   0.50    0.08    -- -103.25 107.00 -36.00  120
 12  ω    -42.00 -11.00   0.50    0.05    --  -48.81 107.00 -36.00   62
 13  ω    -24.00  28.00   0.50    0.05    --   48.81 -19.00-120.00  104
 14  ω     39.00  68.00   0.50    0.08    --  101.25 -57.00 120.00   58
 15  ω     40.00  68.00   0.50    0.08    --  101.25 -57.00  60.00   56
 16  ω     32.00  69.00   0.50    0.08    --  101.25 -57.00  30.00   74
 17  ω     29.00  67.00   0.50    0.08    --  101.25 -57.00   0.00   76
 18  ω     29.00  69.00   0.50    0.08    --  101.25 -57.00-150.00   80
 19  ω     33.00  99.00   0.50    0.08    --  101.25 -99.00-120.00  132
 20  ω     62.00 104.00   0.50    0.08    --  101.25-107.00-135.00   84
 21  ω     53.00  90.00   0.50    0.05    --   48.81-125.00 -90.00   74
 22  ω      6.00  49.00   0.50    0.05    --   48.81-107.00-135.00   86
 23  ω     94.00 120.00   0.50    0.08    --  101.25  57.00 -60.00   52
 24  ω    144.00 169.00   0.50    0.08    --  101.25  57.00 -60.00   50
 25  ω     97.00 156.00   0.50    0.08    --  101.25 107.00 -36.00  118
 26  ω     93.00 172.00   0.50    0.08    --  101.25  57.00 120.00  158
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1086573000
_diffrn_orient_matrix_UB_12      -0.0055824000
_diffrn_orient_matrix_UB_13      0.0492199000
_diffrn_orient_matrix_UB_21      0.0239562000
_diffrn_orient_matrix_UB_22      0.0729497000
_diffrn_orient_matrix_UB_23      -0.0091170000
_diffrn_orient_matrix_UB_31      -0.0609405000
_diffrn_orient_matrix_UB_32      0.0187135000
_diffrn_orient_matrix_UB_33      0.0504970000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9298
_reflns_number_total             10996
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.550
_refine_diff_density_min         -0.774
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     502
_refine_ls_number_reflns         10996
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0421
_refine_ls_restrained_S_all      1.049
_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)+(0.0569P)²+9.0520P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1168
_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.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C7(H7), C9(H9), C10(H10), C13(H13), C18(H18), C20(H20),
 C36(H36), C38(H38)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C40(H40A,H40B,
 H40C), C41(H41A,H41B,H41C), C42(H42A,H42B,H42C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Br1 Br 0.25707(4) 0.54373(2) 0.82410(2) 0.05502(13) Uani 1 1 d . . . . .
Br2 Br -0.07325(4) 0.41333(2) 0.87458(2) 0.05986(14) Uani 1 1 d . . . . .
Br3 Br 0.09589(5) 0.27101(2) 0.71585(3) 0.06544(16) Uani 1 1 d . . . . .
Br4 Br 0.59556(4) 0.18433(2) 0.51076(2) 0.05239(13) Uani 1 1 d . . . . .
Br5 Br 0.78444(4) 0.31151(2) 0.51701(2) 0.05991(14) Uani 1 1 d . . . . .
Br6 Br 0.88520(4) 0.46148(2) 0.58803(2) 0.05365(12) Uani 1 1 d . . . . .
Br7 Br 0.82825(4) 0.59933(2) 0.66753(2) 0.05469(13) Uani 1 1 d . . . . .
Ni1 Ni 0.48338(5) 0.40107(3) 0.65798(3) 0.03426(14) Uani 1 1 d . . . . .
N1 N 0.4356(3) 0.46376(13) 0.70700(14) 0.0349(6) Uani 1 1 d . . . . .
N2 N 0.2849(3) 0.40494(13) 0.73001(13) 0.0355(6) Uani 1 1 d . . . . .
N3 N 0.3717(3) 0.34263(13) 0.66394(13) 0.0359(6) Uani 1 1 d . . . . .
N4 N 0.5426(3) 0.34436(14) 0.60917(14) 0.0385(7) Uani 1 1 d . . . . .
N5 N 0.6013(3) 0.45224(13) 0.64885(14) 0.0378(7) Uani 1 1 d . . . . .
C1 C 0.4834(3) 0.52552(16) 0.72118(17) 0.0372(8) Uani 1 1 d . . . . .
C2 C 0.4258(3) 0.55874(18) 0.75965(17) 0.0418(8) Uani 1 1 d . . . . .
H2 H 0.440621 0.601863 0.775434 0.050 Uiso 1 1 calc R U . . .
C3 C 0.3455(3) 0.51845(17) 0.77020(17) 0.0403(8) Uani 1 1 d . . . . .
C4 C 0.3520(3) 0.45882(16) 0.73558(16) 0.0352(7) Uani 1 1 d . . . . .
C5 C 0.1975(3) 0.40610(16) 0.76373(16) 0.0364(8) Uani 1 1 d . . . . .
C6 C 0.0996(3) 0.43577(18) 0.73750(18) 0.0415(8) Uani 1 1 d . . . . .
H6 H 0.088024 0.454443 0.697440 0.050 Uiso 1 1 calc R U . . .
C7 C 0.0173(4) 0.43816(18) 0.7704(2) 0.0463(9) Uani 1 1 d . . . . .
H7 H -0.051355 0.458677 0.753349 0.056 Uiso 1 1 calc R U . . .
C8 C 0.0375(4) 0.40991(18) 0.82852(19) 0.0452(9) Uani 1 1 d . . . . .
C9 C 0.1355(4) 0.3801(2) 0.85390(19) 0.0490(10) Uani 1 1 d . . . . .
H9 H 0.146923 0.360743 0.893667 0.059 Uiso 1 1 calc R U . . .
C10 C 0.2181(4) 0.37823(18) 0.82150(18) 0.0453(9) Uani 1 1 d . . . . .
H10 H 0.287114 0.358230 0.838718 0.054 Uiso 1 1 calc R U . . .
C11 C 0.2923(3) 0.35041(16) 0.69556(17) 0.0366(8) Uani 1 1 d . . . . .
C12 C 0.2206(3) 0.29315(18) 0.68671(19) 0.0440(9) Uani 1 1 d . . . . .
C13 C 0.2605(4) 0.25176(18) 0.64914(19) 0.0455(9) Uani 1 1 d . . . . .
H13 H 0.230750 0.210166 0.635132 0.055 Uiso 1 1 calc R U . . .
C14 C 0.3541(3) 0.28132(16) 0.63450(17) 0.0375(8) Uani 1 1 d . . . . .
C15 C 0.4174(3) 0.25262(16) 0.59720(17) 0.0387(8) Uani 1 1 d . . . . .
C16 C 0.3848(3) 0.18613(16) 0.57143(17) 0.0385(8) Uani 1 1 d . . . . .
C17 C 0.4246(3) 0.13053(17) 0.60615(18) 0.0420(8) Uani 1 1 d . . . . .
C18 C 0.3973(4) 0.06923(17) 0.57983(19) 0.0459(10) Uani 1 1 d . . . . .
H18 H 0.425202 0.031244 0.602826 0.055 Uiso 1 1 calc R U . . .
C19 C 0.3311(4) 0.06165(18) 0.5214(2) 0.0514(11) Uani 1 1 d . . . . .
C20 C 0.2919(4) 0.1172(2) 0.4889(2) 0.0532(10) Uani 1 1 d . . . . .
H20 H 0.245613 0.112572 0.448884 0.064 Uiso 1 1 calc R U . . .
C21 C 0.3170(4) 0.18015(18) 0.51219(18) 0.0447(9) Uani 1 1 d . . . . .
C22 C 0.4964(4) 0.1356(2) 0.6696(2) 0.0534(10) Uani 1 1 d . . . . .
H22A H 0.562940 0.160540 0.668051 0.080 Uiso 1 1 calc R U . . .
H22B H 0.517098 0.091607 0.685683 0.080 Uiso 1 1 calc R U . . .
H22C H 0.456208 0.158119 0.696602 0.080 Uiso 1 1 calc R U . . .
C23 C 0.3046(6) -0.0060(2) 0.4940(3) 0.0754(16) Uani 1 1 d . . . . .
H23A H 0.372926 -0.028097 0.490926 0.113 Uiso 1 1 calc R U . . .
H23B H 0.256057 -0.002071 0.452816 0.113 Uiso 1 1 calc R U . . .
H23C H 0.267535 -0.031677 0.520573 0.113 Uiso 1 1 calc R U . . .
C24 C 0.2762(5) 0.2396(2) 0.4733(2) 0.0644(13) Uani 1 1 d . . . . .
H24A H 0.259257 0.274667 0.499716 0.097 Uiso 1 1 calc R U . . .
H24B H 0.209570 0.228091 0.442265 0.097 Uiso 1 1 calc R U . . .
H24C H 0.333313 0.254507 0.452608 0.097 Uiso 1 1 calc R U . . .
C25 C 0.5112(3) 0.28369(16) 0.58542(17) 0.0378(8) Uani 1 1 d . . . . .
C26 C 0.5896(3) 0.26408(17) 0.55164(17) 0.0397(8) Uani 1 1 d . . . . .
C27 C 0.6658(3) 0.31362(17) 0.55455(17) 0.0385(8) Uani 1 1 d . . . . .
C28 C 0.6351(3) 0.36353(17) 0.59146(17) 0.0382(8) Uani 1 1 d . . . . .
C29 C 0.6719(3) 0.42667(17) 0.61651(17) 0.0389(8) Uani 1 1 d . . . . .
C30 C 0.7593(3) 0.47126(18) 0.61897(18) 0.0406(8) Uani 1 1 d . . . . .
C31 C 0.7374(3) 0.52517(18) 0.65178(18) 0.0426(8) Uani 1 1 d . . . . .
C32 C 0.6370(3) 0.51349(16) 0.67056(17) 0.0378(8) Uani 1 1 d . . . . .
C33 C 0.5773(3) 0.54999(16) 0.70470(16) 0.0379(8) Uani 1 1 d . . . . .
C34 C 0.6094(3) 0.61886(17) 0.72386(17) 0.0376(8) Uani 1 1 d . . . . .
C35 C 0.5730(3) 0.66974(18) 0.68218(19) 0.0426(8) Uani 1 1 d . . . . .
C36 C 0.6026(4) 0.73376(18) 0.7013(2) 0.0458(9) Uani 1 1 d . . . . .
H36 H 0.579339 0.768893 0.673372 0.055 Uiso 1 1 calc R U . . .
C37 C 0.6651(4) 0.74751(18) 0.7602(2) 0.0472(9) Uani 1 1 d . . . . .
C38 C 0.6983(4) 0.69574(19) 0.80005(19) 0.0465(9) Uani 1 1 d . . . . .
H38 H 0.740104 0.704635 0.840542 0.056 Uiso 1 1 calc R U . . .
C39 C 0.6728(4) 0.63113(18) 0.78303(18) 0.0438(9) Uani 1 1 d . . . . .
C40 C 0.7129(4) 0.5759(2) 0.8278(2) 0.0571(11) Uani 1 1 d . . . . .
H40A H 0.754928 0.593958 0.866852 0.086 Uiso 1 1 calc R U . . .
H40B H 0.760198 0.546538 0.810320 0.086 Uiso 1 1 calc R U . . .
H40C H 0.649548 0.551279 0.835073 0.086 Uiso 1 1 calc R U . . .
C41 C 0.6934(4) 0.8172(2) 0.7800(2) 0.0603(12) Uani 1 1 d . . . . .
H41A H 0.687645 0.844868 0.743367 0.090 Uiso 1 1 calc R U . . .
H41B H 0.768892 0.819012 0.805159 0.090 Uiso 1 1 calc R U . . .
H41C H 0.642207 0.833066 0.804205 0.090 Uiso 1 1 calc R U . . .
C42 C 0.5062(4) 0.6573(2) 0.6183(2) 0.0585(11) Uani 1 1 d . . . . .
H42A H 0.482274 0.699136 0.598062 0.088 Uiso 1 1 calc R U . . .
H42B H 0.441469 0.630893 0.620439 0.088 Uiso 1 1 calc R U . . .
H42C H 0.551098 0.633598 0.594544 0.088 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
Br1 C3 1.877(3) . ?
Br2 C8 1.899(4) . ?
Br3 C12 1.871(4) . ?
Br4 C26 1.874(3) . ?
Br5 C27 1.857(3) . ?
Br6 C30 1.862(4) . ?
Br7 C31 1.875(4) . ?
Ni1 N1 1.865(3) . ?
Ni1 N3 1.860(3) . ?
Ni1 N4 1.851(3) . ?
Ni1 N5 1.851(3) . ?
N1 C1 1.399(4) . ?
N1 C4 1.343(4) . ?
N2 C4 1.370(4) . ?
N2 C5 1.456(4) . ?
N2 C11 1.366(4) . ?
N3 C11 1.348(4) . ?
N3 C14 1.406(4) . ?
N4 C25 1.368(4) . ?
N4 C28 1.359(5) . ?
N5 C29 1.361(4) . ?
N5 C32 1.377(4) . ?
C1 C2 1.410(5) . ?
C1 C33 1.396(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.356(5) . ?
C3 C4 1.452(5) . ?
C5 C6 1.369(6) . ?
C5 C10 1.376(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.390(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.387(6) . ?
C8 C9 1.366(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.457(5) . ?
C12 C13 1.360(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.416(5) . ?
C14 C15 1.397(5) . ?
C15 C16 1.493(5) . ?
C15 C25 1.406(5) . ?
C16 C17 1.399(5) . ?
C16 C21 1.400(6) . ?
C17 C18 1.390(5) . ?
C17 C22 1.493(6) . ?
C18 H18 0.9500 . ?
C18 C19 1.380(7) . ?
C19 C20 1.374(6) . ?
C19 C23 1.516(6) . ?
C20 H20 0.9500 . ?
C20 C21 1.393(5) . ?
C21 C24 1.509(6) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.420(5) . ?
C26 C27 1.378(5) . ?
C27 C28 1.415(5) . ?
C28 C29 1.437(5) . ?
C29 C30 1.411(5) . ?
C30 C31 1.382(5) . ?
C31 C32 1.426(5) . ?
C32 C33 1.395(5) . ?
C33 C34 1.496(5) . ?
C34 C35 1.397(5) . ?
C34 C39 1.396(6) . ?
C35 C36 1.397(5) . ?
C35 C42 1.497(6) . ?
C36 H36 0.9500 . ?
C36 C37 1.393(6) . ?
C37 C38 1.381(6) . ?
C37 C41 1.507(5) . ?
C38 H38 0.9500 . ?
C38 C39 1.388(5) . ?
C39 C40 1.512(6) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 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
N3 Ni1 N1 93.12(12) . . ?
N4 Ni1 N1 174.25(13) . . ?
N4 Ni1 N3 92.62(13) . . ?
N5 Ni1 N1 92.53(13) . . ?
N5 Ni1 N3 174.20(13) . . ?
N5 Ni1 N4 81.72(13) . . ?
C1 N1 Ni1 125.0(2) . . ?
C4 N1 Ni1 127.7(2) . . ?
C4 N1 C1 107.3(3) . . ?
C4 N2 C5 116.9(3) . . ?
C11 N2 C4 125.9(3) . . ?
C11 N2 C5 117.1(3) . . ?
C11 N3 Ni1 127.7(2) . . ?
C11 N3 C14 107.0(3) . . ?
C14 N3 Ni1 125.2(2) . . ?
C25 N4 Ni1 132.5(2) . . ?
C28 N4 Ni1 117.9(2) . . ?
C28 N4 C25 109.6(3) . . ?
C29 N5 Ni1 117.8(2) . . ?
C29 N5 C32 109.7(3) . . ?
C32 N5 Ni1 132.5(2) . . ?
N1 C1 C2 108.7(3) . . ?
C33 C1 N1 127.0(3) . . ?
C33 C1 C2 124.1(3) . . ?
C1 C2 H2 125.9 . . ?
C3 C2 C1 108.2(3) . . ?
C3 C2 H2 125.9 . . ?
C2 C3 Br1 120.5(3) . . ?
C2 C3 C4 106.5(3) . . ?
C4 C3 Br1 132.9(3) . . ?
N1 C4 N2 122.8(3) . . ?
N1 C4 C3 109.4(3) . . ?
N2 C4 C3 127.9(3) . . ?
C6 C5 N2 119.1(3) . . ?
C6 C5 C10 122.7(3) . . ?
C10 C5 N2 118.2(3) . . ?
C5 C6 H6 120.5 . . ?
C5 C6 C7 119.0(4) . . ?
C7 C6 H6 120.5 . . ?
C6 C7 H7 120.8 . . ?
C8 C7 C6 118.5(4) . . ?
C8 C7 H7 120.8 . . ?
C7 C8 Br2 119.2(3) . . ?
C9 C8 Br2 119.0(3) . . ?
C9 C8 C7 121.8(4) . . ?
C8 C9 H9 120.1 . . ?
C8 C9 C10 119.8(4) . . ?
C10 C9 H9 120.1 . . ?
C5 C10 C9 118.2(4) . . ?
C5 C10 H10 120.9 . . ?
C9 C10 H10 120.9 . . ?
N2 C11 C12 127.7(3) . . ?
N3 C11 N2 122.7(3) . . ?
N3 C11 C12 109.6(3) . . ?
C11 C12 Br3 132.8(3) . . ?
C13 C12 Br3 120.8(3) . . ?
C13 C12 C11 106.4(3) . . ?
C12 C13 H13 125.9 . . ?
C12 C13 C14 108.2(3) . . ?
C14 C13 H13 125.9 . . ?
N3 C14 C13 108.7(3) . . ?
C15 C14 N3 126.9(3) . . ?
C15 C14 C13 124.4(3) . . ?
C14 C15 C16 117.9(3) . . ?
C14 C15 C25 121.8(3) . . ?
C25 C15 C16 120.3(3) . . ?
C17 C16 C15 119.6(4) . . ?
C17 C16 C21 120.8(3) . . ?
C21 C16 C15 119.6(3) . . ?
C16 C17 C22 121.8(3) . . ?
C18 C17 C16 118.4(4) . . ?
C18 C17 C22 119.8(4) . . ?
C17 C18 H18 118.9 . . ?
C19 C18 C17 122.3(4) . . ?
C19 C18 H18 118.9 . . ?
C18 C19 C23 120.7(4) . . ?
C20 C19 C18 117.9(4) . . ?
C20 C19 C23 121.4(5) . . ?
C19 C20 H20 118.6 . . ?
C19 C20 C21 122.8(4) . . ?
C21 C20 H20 118.6 . . ?
C16 C21 C24 121.5(4) . . ?
C20 C21 C16 117.8(4) . . ?
C20 C21 C24 120.6(4) . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C19 C23 H23A 109.5 . . ?
C19 C23 H23B 109.5 . . ?
C19 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N4 C25 C15 120.8(3) . . ?
N4 C25 C26 106.8(3) . . ?
C15 C25 C26 132.3(3) . . ?
C25 C26 Br4 127.6(3) . . ?
C27 C26 Br4 123.8(3) . . ?
C27 C26 C25 108.6(3) . . ?
C26 C27 Br5 124.9(3) . . ?
C26 C27 C28 106.3(3) . . ?
C28 C27 Br5 128.8(3) . . ?
N4 C28 C27 108.7(3) . . ?
N4 C28 C29 111.2(3) . . ?
C27 C28 C29 140.0(3) . . ?
N5 C29 C28 111.2(3) . . ?
N5 C29 C30 108.6(3) . . ?
C30 C29 C28 140.2(3) . . ?
C29 C30 Br6 128.7(3) . . ?
C31 C30 Br6 124.4(3) . . ?
C31 C30 C29 106.8(3) . . ?
C30 C31 Br7 123.9(3) . . ?
C30 C31 C32 108.3(3) . . ?
C32 C31 Br7 127.8(3) . . ?
N5 C32 C31 106.5(3) . . ?
N5 C32 C33 120.4(3) . . ?
C33 C32 C31 133.1(3) . . ?
C1 C33 C34 116.5(3) . . ?
C32 C33 C1 122.4(3) . . ?
C32 C33 C34 121.0(3) . . ?
C35 C34 C33 118.9(3) . . ?
C39 C34 C33 119.6(3) . . ?
C39 C34 C35 121.4(3) . . ?
C34 C35 C42 122.0(3) . . ?
C36 C35 C34 118.0(4) . . ?
C36 C35 C42 120.0(4) . . ?
C35 C36 H36 119.1 . . ?
C37 C36 C35 121.8(4) . . ?
C37 C36 H36 119.1 . . ?
C36 C37 C41 120.6(4) . . ?
C38 C37 C36 118.2(3) . . ?
C38 C37 C41 121.2(4) . . ?
C37 C38 H38 118.8 . . ?
C37 C38 C39 122.3(4) . . ?
C39 C38 H38 118.8 . . ?
C34 C39 C40 121.2(3) . . ?
C38 C39 C34 118.2(4) . . ?
C38 C39 C40 120.5(4) . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C37 C41 H41A 109.5 . . ?
C37 C41 H41B 109.5 . . ?
C37 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C35 C42 H42A 109.5 . . ?
C35 C42 H42B 109.5 . . ?
C35 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 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
Br1 C3 C4 N1 -175.5(3) . . . . ?
Br1 C3 C4 N2 5.8(7) . . . . ?
Br2 C8 C9 C10 -178.8(3) . . . . ?
Br3 C12 C13 C14 179.8(3) . . . . ?
Br4 C26 C27 Br5 1.9(5) . . . . ?
Br4 C26 C27 C28 -177.4(3) . . . . ?
Br5 C27 C28 N4 179.9(3) . . . . ?
Br5 C27 C28 C29 -1.5(8) . . . . ?
Br6 C30 C31 Br7 2.9(5) . . . . ?
Br6 C30 C31 C32 -176.9(3) . . . . ?
Br7 C31 C32 N5 -179.3(3) . . . . ?
Br7 C31 C32 C33 -0.5(7) . . . . ?
Ni1 N1 C1 C2 -179.4(3) . . . . ?
Ni1 N1 C1 C33 -3.8(5) . . . . ?
Ni1 N1 C4 N2 -2.7(5) . . . . ?
Ni1 N1 C4 C3 178.5(3) . . . . ?
Ni1 N3 C11 N2 -1.3(5) . . . . ?
Ni1 N3 C11 C12 178.9(3) . . . . ?
Ni1 N3 C14 C13 -178.9(3) . . . . ?
Ni1 N3 C14 C15 1.6(6) . . . . ?
Ni1 N4 C25 C15 -0.4(6) . . . . ?
Ni1 N4 C25 C26 -179.6(3) . . . . ?
Ni1 N4 C28 C27 -179.7(3) . . . . ?
Ni1 N4 C28 C29 1.3(4) . . . . ?
Ni1 N5 C29 C28 3.7(4) . . . . ?
Ni1 N5 C29 C30 -175.7(3) . . . . ?
Ni1 N5 C32 C31 176.0(3) . . . . ?
Ni1 N5 C32 C33 -2.9(6) . . . . ?
N1 Ni1 N3 C11 -1.0(3) . . . . ?
N1 Ni1 N3 C14 177.9(3) . . . . ?
N1 Ni1 N5 C29 177.3(3) . . . . ?
N1 Ni1 N5 C32 -0.3(4) . . . . ?
N1 C1 C2 C3 1.1(5) . . . . ?
N1 C1 C33 C32 -0.1(6) . . . . ?
N1 C1 C33 C34 178.0(4) . . . . ?
N2 C5 C6 C7 -178.5(3) . . . . ?
N2 C5 C10 C9 179.2(3) . . . . ?
N2 C11 C12 Br3 0.5(7) . . . . ?
N2 C11 C12 C13 -179.7(4) . . . . ?
N3 Ni1 N1 C1 -177.8(3) . . . . ?
N3 Ni1 N1 C4 3.0(3) . . . . ?
N3 Ni1 N4 C25 2.1(4) . . . . ?
N3 Ni1 N4 C28 -178.1(3) . . . . ?
N3 C11 C12 Br3 -179.7(3) . . . . ?
N3 C11 C12 C13 0.1(5) . . . . ?
N3 C14 C15 C16 178.9(4) . . . . ?
N3 C14 C15 C25 0.9(6) . . . . ?
N4 Ni1 N3 C11 178.6(3) . . . . ?
N4 Ni1 N3 C14 -2.5(3) . . . . ?
N4 Ni1 N5 C29 -2.5(3) . . . . ?
N4 Ni1 N5 C32 179.9(4) . . . . ?
N4 C25 C26 Br4 177.4(3) . . . . ?
N4 C25 C26 C27 -1.1(4) . . . . ?
N4 C28 C29 N5 -3.1(5) . . . . ?
N4 C28 C29 C30 176.2(5) . . . . ?
N5 Ni1 N1 C1 3.5(3) . . . . ?
N5 Ni1 N1 C4 -175.7(3) . . . . ?
N5 Ni1 N4 C25 -179.2(4) . . . . ?
N5 Ni1 N4 C28 0.6(3) . . . . ?
N5 C29 C30 Br6 175.6(3) . . . . ?
N5 C29 C30 C31 -2.0(5) . . . . ?
N5 C32 C33 C1 3.5(6) . . . . ?
N5 C32 C33 C34 -174.6(3) . . . . ?
C1 N1 C4 N2 178.0(3) . . . . ?
C1 N1 C4 C3 -0.8(4) . . . . ?
C1 C2 C3 Br1 175.9(3) . . . . ?
C1 C2 C3 C4 -1.6(5) . . . . ?
C1 C33 C34 C35 -94.4(4) . . . . ?
C1 C33 C34 C39 84.4(5) . . . . ?
C2 C1 C33 C32 174.8(4) . . . . ?
C2 C1 C33 C34 -7.1(6) . . . . ?
C2 C3 C4 N1 1.5(5) . . . . ?
C2 C3 C4 N2 -177.2(4) . . . . ?
C4 N1 C1 C2 -0.1(4) . . . . ?
C4 N1 C1 C33 175.5(4) . . . . ?
C4 N2 C5 C6 84.9(4) . . . . ?
C4 N2 C5 C10 -93.9(4) . . . . ?
C4 N2 C11 N3 2.5(6) . . . . ?
C4 N2 C11 C12 -177.7(4) . . . . ?
C5 N2 C4 N1 179.8(3) . . . . ?
C5 N2 C4 C3 -1.6(6) . . . . ?
C5 N2 C11 N3 -177.8(3) . . . . ?
C5 N2 C11 C12 2.0(6) . . . . ?
C5 C6 C7 C8 -0.4(6) . . . . ?
C6 C5 C10 C9 0.5(6) . . . . ?
C6 C7 C8 Br2 179.4(3) . . . . ?
C6 C7 C8 C9 0.0(6) . . . . ?
C7 C8 C9 C10 0.7(6) . . . . ?
C8 C9 C10 C5 -0.9(6) . . . . ?
C10 C5 C6 C7 0.2(6) . . . . ?
C11 N2 C4 N1 -0.4(6) . . . . ?
C11 N2 C4 C3 178.2(4) . . . . ?
C11 N2 C5 C6 -94.9(4) . . . . ?
C11 N2 C5 C10 86.4(4) . . . . ?
C11 N3 C14 C13 0.2(4) . . . . ?
C11 N3 C14 C15 -179.3(4) . . . . ?
C11 C12 C13 C14 0.0(5) . . . . ?
C12 C13 C14 N3 -0.1(5) . . . . ?
C12 C13 C14 C15 179.4(4) . . . . ?
C13 C14 C15 C16 -0.5(6) . . . . ?
C13 C14 C15 C25 -178.5(4) . . . . ?
C14 N3 C11 N2 179.7(4) . . . . ?
C14 N3 C11 C12 -0.1(4) . . . . ?
C14 C15 C16 C17 -86.9(5) . . . . ?
C14 C15 C16 C21 94.8(4) . . . . ?
C14 C15 C25 N4 -1.5(6) . . . . ?
C14 C15 C25 C26 177.5(4) . . . . ?
C15 C16 C17 C18 -176.9(3) . . . . ?
C15 C16 C17 C22 2.1(5) . . . . ?
C15 C16 C21 C20 177.6(4) . . . . ?
C15 C16 C21 C24 0.2(6) . . . . ?
C15 C25 C26 Br4 -1.7(7) . . . . ?
C15 C25 C26 C27 179.8(4) . . . . ?
C16 C15 C25 N4 -179.5(4) . . . . ?
C16 C15 C25 C26 -0.5(7) . . . . ?
C16 C17 C18 C19 -1.1(6) . . . . ?
C17 C16 C21 C20 -0.7(6) . . . . ?
C17 C16 C21 C24 -178.0(4) . . . . ?
C17 C18 C19 C20 0.1(6) . . . . ?
C17 C18 C19 C23 179.1(4) . . . . ?
C18 C19 C20 C21 0.6(6) . . . . ?
C19 C20 C21 C16 -0.4(6) . . . . ?
C19 C20 C21 C24 177.0(4) . . . . ?
C21 C16 C17 C18 1.4(5) . . . . ?
C21 C16 C17 C22 -179.6(4) . . . . ?
C22 C17 C18 C19 179.8(4) . . . . ?
C23 C19 C20 C21 -178.3(4) . . . . ?
C25 N4 C28 C27 0.1(4) . . . . ?
C25 N4 C28 C29 -178.9(3) . . . . ?
C25 C15 C16 C17 91.1(4) . . . . ?
C25 C15 C16 C21 -87.2(5) . . . . ?
C25 C26 C27 Br5 -179.5(3) . . . . ?
C25 C26 C27 C28 1.1(4) . . . . ?
C26 C27 C28 N4 -0.8(4) . . . . ?
C26 C27 C28 C29 177.8(5) . . . . ?
C27 C28 C29 N5 178.4(5) . . . . ?
C27 C28 C29 C30 -2.4(9) . . . . ?
C28 N4 C25 C15 179.8(4) . . . . ?
C28 N4 C25 C26 0.6(4) . . . . ?
C28 C29 C30 Br6 -3.6(8) . . . . ?
C28 C29 C30 C31 178.7(5) . . . . ?
C29 N5 C32 C31 -1.7(4) . . . . ?
C29 N5 C32 C33 179.3(3) . . . . ?
C29 C30 C31 Br7 -179.3(3) . . . . ?
C29 C30 C31 C32 0.9(5) . . . . ?
C30 C31 C32 N5 0.5(4) . . . . ?
C30 C31 C32 C33 179.2(4) . . . . ?
C31 C32 C33 C1 -175.1(4) . . . . ?
C31 C32 C33 C34 6.9(7) . . . . ?
C32 N5 C29 C28 -178.2(3) . . . . ?
C32 N5 C29 C30 2.4(4) . . . . ?
C32 C33 C34 C35 83.8(5) . . . . ?
C32 C33 C34 C39 -97.5(4) . . . . ?
C33 C1 C2 C3 -174.7(4) . . . . ?
C33 C34 C35 C36 179.1(3) . . . . ?
C33 C34 C35 C42 -2.1(6) . . . . ?
C33 C34 C39 C38 -178.0(4) . . . . ?
C33 C34 C39 C40 1.9(6) . . . . ?
C34 C35 C36 C37 -0.8(6) . . . . ?
C35 C34 C39 C38 0.7(6) . . . . ?
C35 C34 C39 C40 -179.4(4) . . . . ?
C35 C36 C37 C38 0.2(6) . . . . ?
C35 C36 C37 C41 -178.6(4) . . . . ?
C36 C37 C38 C39 0.9(6) . . . . ?
C37 C38 C39 C34 -1.4(6) . . . . ?
C37 C38 C39 C40 178.8(4) . . . . ?
C39 C34 C35 C36 0.3(6) . . . . ?
C39 C34 C35 C42 179.2(4) . . . . ?
C41 C37 C38 C39 179.7(4) . . . . ?
C42 C35 C36 C37 -179.7(4) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.515 -0.743 0.000 1016.1 275.4 ?
2 -0.308 -0.598 0.500 1016.1 275.4 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.681
_oxdiff_exptl_absorpt_empirical_full_min 0.741
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2266358'
loop_
_audit_author_name
_audit_author_address
'Xiaofang Li'
;HUNAN university of science and technology
China
;
_audit_update_record             
;
2023-05-30 deposited with the CCDC.	2023-07-21 downloaded from the CCDC.
;
_audit_creation_date             2023-04-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C42 H32 Br N7 Ni O4), C H2 Cl2'
_chemical_formula_sum            'C85 H66 Br2 Cl2 N14 Ni2 O8'
_chemical_formula_weight         1759.65
_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 0.0033 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'
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'

_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                   12.2073(11)
_cell_length_b                   14.4368(13)
_cell_length_c                   23.448(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4132.4(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9887
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      24.75
_cell_measurement_theta_min      2.18
_shelx_estimated_absorpt_T_max   0.768
_shelx_estimated_absorpt_T_min   0.671
_exptl_absorpt_coefficient_mu    1.551
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   None
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Blue
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             1796
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0835
_diffrn_reflns_av_unetI/netI     0.0663
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            36710
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.010
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_min         2.351
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.788
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                5827
_reflns_number_total             7253
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.044(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     530
_refine_ls_number_reflns         7253
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0492
_refine_ls_restrained_S_all      1.048
_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)+(0.0759P)²+0.0709P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1286
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.956(15)
 0.044(15)
2. 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
3. Uiso/Uaniso restraints and constraints
Uanis(C43) \\sim Ueq, Uanis(Cl2) \\sim Ueq, Uanis(Cl1) \\sim Ueq: with sigma of
0.002 and sigma for terminal atoms of 0.004
4. Others
 Fixed Sof: Cl1(0.5) Cl2(0.5) C43(0.5) H43A(0.5) H43B(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C43(H43A,H43B)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C8(H8), C11(H11), C16(H16), C17(H17), C20(H20), C21(H21),
 C23(H23), C24(H24), C27(H27), C29(H29), C36(H36), C38(H38)
5.c Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C40(H40A,H40B,
 H40C), C41(H41A,H41B,H41C), C42(H42A,H42B,H42C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Br1 Br -0.15946(8) 1.17619(6) 0.38097(5) 0.0884(4) Uani 1 1 d . . . . .
Ni1 Ni 0.19362(6) 0.61155(5) 0.42740(3) 0.0338(2) Uani 1 1 d . . . . .
Cl1 Cl -0.0079(11) 0.6600(9) 0.2953(6) 0.203(4) Uani 0.5 1 d . U P . .
Cl2 Cl -0.0521(15) 0.4522(12) 0.3072(8) 0.260(7) Uani 0.5 1 d . U P . .
O1 O 0.1063(5) 0.2361(5) 0.5544(4) 0.111(3) Uani 1 1 d . . . . .
O2 O -0.0344(5) 0.2772(4) 0.5083(4) 0.093(2) Uani 1 1 d . . . . .
O3 O 0.5803(7) 0.5496(5) 0.2838(4) 0.114(3) Uani 1 1 d . . . . .
O4 O 0.6449(5) 0.4513(6) 0.3412(3) 0.109(3) Uani 1 1 d . . . . .
N1 N 0.0605(4) 0.6518(3) 0.4557(2) 0.0379(12) Uani 1 1 d . . . . .
N2 N 0.2259(4) 0.7232(3) 0.3927(2) 0.0354(12) Uani 1 1 d . . . . .
N3 N 0.3239(4) 0.5608(3) 0.4021(2) 0.0378(12) Uani 1 1 d . . . . .
N4 N 0.1743(4) 0.4964(3) 0.4586(2) 0.0392(12) Uani 1 1 d . . . . .
N5 N 0.0647(4) 0.8055(3) 0.4192(2) 0.0351(11) Uani 1 1 d . . . . .
N6 N 0.0625(5) 0.2884(4) 0.5236(3) 0.0544(16) Uani 1 1 d . . . . .
N7 N 0.5780(6) 0.5070(5) 0.3283(3) 0.0634(18) Uani 1 1 d . . . . .
C1 C 0.0145(5) 0.7357(4) 0.4491(3) 0.0360(14) Uani 1 1 d . . . . .
C2 C -0.0882(5) 0.7424(4) 0.4767(3) 0.0445(16) Uani 1 1 d . . . . .
H2 H -0.134431 0.793596 0.477652 0.053 Uiso 1 1 calc R U . . .
C3 C -0.1052(5) 0.6589(4) 0.5016(3) 0.0412(15) Uani 1 1 d . . . . .
H3 H -0.165740 0.642464 0.523423 0.049 Uiso 1 1 calc R U . . .
C4 C -0.0137(5) 0.6002(4) 0.4884(3) 0.0396(14) Uani 1 1 d . . . . .
C5 C -0.0013(5) 0.5079(4) 0.5053(3) 0.0384(14) Uani 1 1 d . . . . .
C6 C 0.0897(5) 0.4555(4) 0.4878(3) 0.0433(15) Uani 1 1 d . . . . .
C7 C 0.1233(5) 0.3624(4) 0.4975(3) 0.0477(17) Uani 1 1 d . . . . .
C8 C 0.2271(5) 0.3485(4) 0.4759(3) 0.0436(16) Uani 1 1 d . . . . .
H8 H 0.269257 0.294923 0.477900 0.052 Uiso 1 1 calc R U . . .
C9 C 0.2549(5) 0.4334(4) 0.4503(3) 0.0398(15) Uani 1 1 d . . . . .
C10 C 0.3428(5) 0.4707(4) 0.4177(3) 0.0403(15) Uani 1 1 d . . . . .
C11 C 0.4436(5) 0.4408(4) 0.3956(3) 0.0425(15) Uani 1 1 d . . . . .
H11 H 0.477726 0.383907 0.401036 0.051 Uiso 1 1 calc R U . . .
C12 C 0.4809(5) 0.5155(4) 0.3639(3) 0.0432(16) Uani 1 1 d . . . . .
C13 C 0.4070(5) 0.5922(4) 0.3682(3) 0.0393(14) Uani 1 1 d . . . . .
C14 C 0.4071(5) 0.6857(4) 0.3499(3) 0.0386(14) Uani 1 1 d . . . . .
C15 C 0.3216(5) 0.7450(4) 0.3622(2) 0.0355(13) Uani 1 1 d . . . . .
C16 C 0.3140(6) 0.8409(4) 0.3459(3) 0.0455(15) Uani 1 1 d . . . . .
H16 H 0.366906 0.874110 0.326018 0.055 Uiso 1 1 calc R U . . .
C17 C 0.2180(5) 0.8741(4) 0.3642(3) 0.0432(16) Uani 1 1 d . . . . .
H17 H 0.191199 0.933828 0.359107 0.052 Uiso 1 1 calc R U . . .
C18 C 0.1653(5) 0.8005(4) 0.3929(3) 0.0362(14) Uani 1 1 d . . . . .
C19 C 0.0059(5) 0.8935(4) 0.4121(3) 0.0390(14) Uani 1 1 d . . . . .
C20 C 0.0060(6) 0.9577(4) 0.4546(3) 0.0453(15) Uani 1 1 d . . . . .
H20 H 0.039945 0.944988 0.489280 0.054 Uiso 1 1 calc R U . . .
C21 C -0.0457(6) 1.0434(4) 0.4456(3) 0.0514(18) Uani 1 1 d . . . . .
H21 H -0.046438 1.088211 0.474121 0.062 Uiso 1 1 calc R U . . .
C22 C -0.0943(6) 1.0594(5) 0.3949(4) 0.0535(19) Uani 1 1 d . . . . .
C23 C -0.0953(7) 0.9951(5) 0.3531(4) 0.066(2) Uani 1 1 d . . . . .
H23 H -0.129305 1.007957 0.318501 0.080 Uiso 1 1 calc R U . . .
C24 C -0.0457(6) 0.9098(5) 0.3617(3) 0.057(2) Uani 1 1 d . . . . .
H24 H -0.047735 0.864578 0.333513 0.068 Uiso 1 1 calc R U . . .
C25 C -0.0851(5) 0.4669(4) 0.5449(3) 0.0404(15) Uani 1 1 d . . . . .
C26 C -0.1860(6) 0.4373(4) 0.5231(3) 0.0493(16) Uani 1 1 d . . . . .
C27 C -0.2601(5) 0.3952(5) 0.5601(3) 0.0548(19) Uani 1 1 d . . . . .
H27 H -0.327053 0.374263 0.546275 0.066 Uiso 1 1 calc R U . . .
C28 C -0.2349(6) 0.3841(5) 0.6174(4) 0.061(2) Uani 1 1 d . . . . .
C29 C -0.1360(6) 0.4150(5) 0.6377(3) 0.056(2) Uani 1 1 d . . . . .
H29 H -0.119821 0.408532 0.676265 0.067 Uiso 1 1 calc R U . . .
C30 C -0.0581(6) 0.4567(4) 0.6011(3) 0.0451(16) Uani 1 1 d . . . . .
C31 C -0.2154(7) 0.4441(6) 0.4610(4) 0.074(2) Uani 1 1 d . . . . .
H31A H -0.212034 0.507685 0.449182 0.111 Uiso 1 1 calc R U . . .
H31B H -0.288235 0.420849 0.455320 0.111 Uiso 1 1 calc R U . . .
H31C H -0.164632 0.408141 0.438953 0.111 Uiso 1 1 calc R U . . .
C32 C -0.3181(9) 0.3405(7) 0.6578(5) 0.104(4) Uani 1 1 d . . . . .
H32A H -0.360796 0.388394 0.675482 0.156 Uiso 1 1 calc R U . . .
H32B H -0.280435 0.305632 0.686574 0.156 Uiso 1 1 calc R U . . .
H32C H -0.365606 0.300089 0.636654 0.156 Uiso 1 1 calc R U . . .
C33 C 0.0471(7) 0.4913(6) 0.6259(4) 0.066(2) Uani 1 1 d . . . . .
H33A H 0.104259 0.447101 0.618711 0.099 Uiso 1 1 calc R U . . .
H33B H 0.038735 0.499458 0.666324 0.099 Uiso 1 1 calc R U . . .
H33C H 0.065932 0.549455 0.608689 0.099 Uiso 1 1 calc R U . . .
C34 C 0.5003(5) 0.7262(4) 0.3163(3) 0.0414(15) Uani 1 1 d . . . . .
C35 C 0.4872(5) 0.7451(4) 0.2591(3) 0.0440(15) Uani 1 1 d . . . . .
C36 C 0.5705(6) 0.7929(5) 0.2304(3) 0.0553(18) Uani 1 1 d . . . . .
H36 H 0.562231 0.805073 0.191701 0.066 Uiso 1 1 calc R U . . .
C37 C 0.6647(6) 0.8224(5) 0.2576(3) 0.0552(18) Uani 1 1 d . . . . .
C38 C 0.6769(6) 0.7989(5) 0.3151(3) 0.0559(18) Uani 1 1 d . . . . .
H38 H 0.740796 0.815673 0.334137 0.067 Uiso 1 1 calc R U . . .
C39 C 0.5970(5) 0.7519(5) 0.3440(3) 0.0471(16) Uani 1 1 d . . . . .
C40 C 0.3867(7) 0.7149(6) 0.2267(4) 0.065(2) Uani 1 1 d . . . . .
H40A H 0.372023 0.650827 0.234616 0.098 Uiso 1 1 calc R U . . .
H40B H 0.399004 0.722700 0.186509 0.098 Uiso 1 1 calc R U . . .
H40C H 0.325198 0.751771 0.238210 0.098 Uiso 1 1 calc R U . . .
C41 C 0.7506(7) 0.8793(7) 0.2265(4) 0.083(3) Uani 1 1 d . . . . .
H41A H 0.746639 0.942567 0.238982 0.125 Uiso 1 1 calc R U . . .
H41B H 0.737460 0.876378 0.186197 0.125 Uiso 1 1 calc R U . . .
H41C H 0.822079 0.854962 0.234728 0.125 Uiso 1 1 calc R U . . .
C42 C 0.6159(7) 0.7313(7) 0.4074(4) 0.069(2) Uani 1 1 d . . . . .
H42A H 0.681622 0.695546 0.411781 0.103 Uiso 1 1 calc R U . . .
H42B H 0.554779 0.696988 0.422190 0.103 Uiso 1 1 calc R U . . .
H42C H 0.622990 0.788514 0.427959 0.103 Uiso 1 1 calc R U . . .
C43 C -0.092(4) 0.573(3) 0.322(2) 0.211(18) Uani 0.5 1 d . U P . .
H43A H -0.164932 0.582780 0.306213 0.253 Uiso 0.5 1 calc R U P . .
H43B H -0.097147 0.580992 0.362680 0.253 Uiso 0.5 1 calc R U P . .


_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
Br1 C22 1.893(6) . ?
Ni1 N1 1.849(5) . ?
Ni1 N2 1.848(5) . ?
Ni1 N3 1.849(5) . ?
Ni1 N4 1.831(5) . ?
Cl1 C43 1.73(5) . ?
Cl2 C43 1.85(5) . ?
O1 N6 1.174(8) . ?
O2 N6 1.248(8) . ?
O3 N7 1.211(9) . ?
O4 N7 1.184(9) . ?
N1 C1 1.344(7) . ?
N1 C4 1.401(7) . ?
N2 C15 1.406(7) . ?
N2 C18 1.339(7) . ?
N3 C10 1.371(7) . ?
N3 C13 1.366(8) . ?
N4 C6 1.373(8) . ?
N4 C9 1.355(8) . ?
N5 C1 1.373(8) . ?
N5 C18 1.376(8) . ?
N5 C19 1.468(7) . ?
N6 C7 1.436(8) . ?
N7 C12 1.455(9) . ?
C1 C2 1.414(9) . ?
C2 H2 0.9300 . ?
C2 C3 1.355(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.437(9) . ?
C4 C5 1.398(8) . ?
C5 C6 1.405(9) . ?
C5 C25 1.503(9) . ?
C6 C7 1.424(9) . ?
C7 C8 1.379(9) . ?
C8 H8 0.9300 . ?
C8 C9 1.406(8) . ?
C9 C10 1.423(9) . ?
C10 C11 1.403(9) . ?
C11 H11 0.9300 . ?
C11 C12 1.386(9) . ?
C12 C13 1.432(9) . ?
C13 C14 1.417(9) . ?
C14 C15 1.381(8) . ?
C14 C34 1.501(9) . ?
C15 C16 1.438(8) . ?
C16 H16 0.9300 . ?
C16 C17 1.337(9) . ?
C17 H17 0.9300 . ?
C17 C18 1.412(8) . ?
C19 C20 1.362(9) . ?
C19 C24 1.360(9) . ?
C20 H20 0.9300 . ?
C20 C21 1.405(9) . ?
C21 H21 0.9300 . ?
C21 C22 1.349(11) . ?
C22 C23 1.351(11) . ?
C23 H23 0.9300 . ?
C23 C24 1.386(10) . ?
C24 H24 0.9300 . ?
C25 C26 1.402(10) . ?
C25 C30 1.367(10) . ?
C26 C27 1.392(10) . ?
C26 C31 1.502(11) . ?
C27 H27 0.9300 . ?
C27 C28 1.388(12) . ?
C28 C29 1.372(11) . ?
C28 C32 1.524(11) . ?
C29 H29 0.9300 . ?
C29 C30 1.415(10) . ?
C30 C33 1.496(11) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 C35 1.379(9) . ?
C34 C39 1.398(10) . ?
C35 C36 1.401(10) . ?
C35 C40 1.508(10) . ?
C36 H36 0.9300 . ?
C36 C37 1.382(11) . ?
C37 C38 1.398(11) . ?
C37 C41 1.519(10) . ?
C38 H38 0.9300 . ?
C38 C39 1.368(10) . ?
C39 C42 1.533(11) . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C43 H43A 0.9700 . ?
C43 H43B 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
N2 Ni1 N1 94.1(2) . . ?
N2 Ni1 N3 91.2(2) . . ?
N3 Ni1 N1 174.7(2) . . ?
N4 Ni1 N1 91.6(2) . . ?
N4 Ni1 N2 174.3(2) . . ?
N4 Ni1 N3 83.1(2) . . ?
C1 N1 Ni1 127.6(4) . . ?
C1 N1 C4 105.8(5) . . ?
C4 N1 Ni1 126.7(4) . . ?
C15 N2 Ni1 126.6(4) . . ?
C18 N2 Ni1 127.4(4) . . ?
C18 N2 C15 105.9(5) . . ?
C10 N3 Ni1 115.8(4) . . ?
C13 N3 Ni1 134.0(4) . . ?
C13 N3 C10 110.1(5) . . ?
C6 N4 Ni1 133.4(4) . . ?
C9 N4 Ni1 117.3(4) . . ?
C9 N4 C6 109.2(5) . . ?
C1 N5 C18 126.1(5) . . ?
C1 N5 C19 118.3(5) . . ?
C18 N5 C19 115.6(4) . . ?
O1 N6 O2 121.6(6) . . ?
O1 N6 C7 120.4(6) . . ?
O2 N6 C7 117.7(7) . . ?
O3 N7 C12 118.0(7) . . ?
O4 N7 O3 123.3(7) . . ?
O4 N7 C12 118.2(7) . . ?
N1 C1 N5 122.2(5) . . ?
N1 C1 C2 112.4(5) . . ?
N5 C1 C2 125.4(5) . . ?
C1 C2 H2 127.1 . . ?
C3 C2 C1 105.7(5) . . ?
C3 C2 H2 127.1 . . ?
C2 C3 H3 125.9 . . ?
C2 C3 C4 108.3(5) . . ?
C4 C3 H3 125.9 . . ?
N1 C4 C3 107.8(5) . . ?
C5 C4 N1 126.3(5) . . ?
C5 C4 C3 125.9(6) . . ?
C4 C5 C6 121.1(6) . . ?
C4 C5 C25 118.5(5) . . ?
C6 C5 C25 120.4(5) . . ?
N4 C6 C5 120.5(5) . . ?
N4 C6 C7 105.7(5) . . ?
C5 C6 C7 133.6(6) . . ?
C6 C7 N6 128.4(6) . . ?
C8 C7 N6 121.5(5) . . ?
C8 C7 C6 110.1(6) . . ?
C7 C8 H8 127.7 . . ?
C7 C8 C9 104.6(5) . . ?
C9 C8 H8 127.7 . . ?
N4 C9 C8 110.4(5) . . ?
N4 C9 C10 111.7(5) . . ?
C8 C9 C10 137.9(6) . . ?
N3 C10 C9 112.1(5) . . ?
N3 C10 C11 109.9(5) . . ?
C11 C10 C9 138.0(5) . . ?
C10 C11 H11 127.8 . . ?
C12 C11 C10 104.3(5) . . ?
C12 C11 H11 127.8 . . ?
C11 C12 N7 120.7(6) . . ?
C11 C12 C13 110.8(5) . . ?
C13 C12 N7 128.3(6) . . ?
N3 C13 C12 104.7(5) . . ?
N3 C13 C14 119.5(5) . . ?
C14 C13 C12 135.6(6) . . ?
C13 C14 C34 122.1(5) . . ?
C15 C14 C13 121.8(6) . . ?
C15 C14 C34 116.2(5) . . ?
N2 C15 C16 107.3(5) . . ?
C14 C15 N2 126.5(5) . . ?
C14 C15 C16 126.2(6) . . ?
C15 C16 H16 125.8 . . ?
C17 C16 C15 108.4(6) . . ?
C17 C16 H16 125.8 . . ?
C16 C17 H17 126.8 . . ?
C16 C17 C18 106.4(5) . . ?
C18 C17 H17 126.8 . . ?
N2 C18 N5 122.6(5) . . ?
N2 C18 C17 112.0(5) . . ?
N5 C18 C17 125.4(5) . . ?
C20 C19 N5 120.4(6) . . ?
C24 C19 N5 118.4(6) . . ?
C24 C19 C20 121.2(6) . . ?
C19 C20 H20 120.3 . . ?
C19 C20 C21 119.3(7) . . ?
C21 C20 H20 120.3 . . ?
C20 C21 H21 120.6 . . ?
C22 C21 C20 118.8(7) . . ?
C22 C21 H21 120.6 . . ?
C21 C22 Br1 119.3(6) . . ?
C21 C22 C23 121.7(6) . . ?
C23 C22 Br1 118.9(6) . . ?
C22 C23 H23 120.0 . . ?
C22 C23 C24 120.0(7) . . ?
C24 C23 H23 120.0 . . ?
C19 C24 C23 118.9(7) . . ?
C19 C24 H24 120.5 . . ?
C23 C24 H24 120.5 . . ?
C26 C25 C5 119.6(6) . . ?
C30 C25 C5 118.3(6) . . ?
C30 C25 C26 122.0(6) . . ?
C25 C26 C31 122.9(6) . . ?
C27 C26 C25 118.5(7) . . ?
C27 C26 C31 118.5(7) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 C26 120.7(7) . . ?
C28 C27 H27 119.7 . . ?
C27 C28 C32 120.0(8) . . ?
C29 C28 C27 119.5(6) . . ?
C29 C28 C32 120.4(9) . . ?
C28 C29 H29 119.4 . . ?
C28 C29 C30 121.3(7) . . ?
C30 C29 H29 119.4 . . ?
C25 C30 C29 118.0(7) . . ?
C25 C30 C33 123.1(7) . . ?
C29 C30 C33 118.9(7) . . ?
C26 C31 H31A 109.5 . . ?
C26 C31 H31B 109.5 . . ?
C26 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C28 C32 H32A 109.5 . . ?
C28 C32 H32B 109.5 . . ?
C28 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C30 C33 H33A 109.5 . . ?
C30 C33 H33B 109.5 . . ?
C30 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C35 C34 C14 120.0(6) . . ?
C35 C34 C39 119.8(6) . . ?
C39 C34 C14 119.9(6) . . ?
C34 C35 C36 118.7(7) . . ?
C34 C35 C40 121.8(6) . . ?
C36 C35 C40 119.4(7) . . ?
C35 C36 H36 118.9 . . ?
C37 C36 C35 122.3(7) . . ?
C37 C36 H36 118.9 . . ?
C36 C37 C38 117.4(7) . . ?
C36 C37 C41 121.3(8) . . ?
C38 C37 C41 121.3(7) . . ?
C37 C38 H38 119.3 . . ?
C39 C38 C37 121.4(7) . . ?
C39 C38 H38 119.3 . . ?
C34 C39 C42 121.7(6) . . ?
C38 C39 C34 120.3(7) . . ?
C38 C39 C42 118.0(6) . . ?
C35 C40 H40A 109.5 . . ?
C35 C40 H40B 109.5 . . ?
C35 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C37 C41 H41A 109.5 . . ?
C37 C41 H41B 109.5 . . ?
C37 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C39 C42 H42A 109.5 . . ?
C39 C42 H42B 109.5 . . ?
C39 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
Cl1 C43 Cl2 118(3) . . ?
Cl1 C43 H43A 107.9 . . ?
Cl1 C43 H43B 107.9 . . ?
Cl2 C43 H43A 107.9 . . ?
Cl2 C43 H43B 107.9 . . ?
H43A C43 H43B 107.2 . . ?

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
Br1 C22 C23 C24 178.4(6) . . . . ?
Ni1 N1 C1 N5 -0.6(9) . . . . ?
Ni1 N1 C1 C2 -179.9(5) . . . . ?
Ni1 N1 C4 C3 179.3(4) . . . . ?
Ni1 N1 C4 C5 -0.7(9) . . . . ?
Ni1 N2 C15 C14 3.7(9) . . . . ?
Ni1 N2 C15 C16 -176.6(4) . . . . ?
Ni1 N2 C18 N5 -2.0(9) . . . . ?
Ni1 N2 C18 C17 177.1(5) . . . . ?
Ni1 N3 C10 C9 1.0(7) . . . . ?
Ni1 N3 C10 C11 179.7(4) . . . . ?
Ni1 N3 C13 C12 -177.4(5) . . . . ?
Ni1 N3 C13 C14 6.9(10) . . . . ?
Ni1 N4 C6 C5 -8.1(10) . . . . ?
Ni1 N4 C6 C7 176.5(5) . . . . ?
Ni1 N4 C9 C8 -179.0(4) . . . . ?
Ni1 N4 C9 C10 0.2(8) . . . . ?
O1 N6 C7 C6 -140.6(9) . . . . ?
O1 N6 C7 C8 41.8(12) . . . . ?
O2 N6 C7 C6 45.7(11) . . . . ?
O2 N6 C7 C8 -131.9(8) . . . . ?
O3 N7 C12 C11 145.4(8) . . . . ?
O3 N7 C12 C13 -28.7(12) . . . . ?
O4 N7 C12 C11 -26.4(12) . . . . ?
O4 N7 C12 C13 159.5(8) . . . . ?
N1 Ni1 N2 C15 178.5(5) . . . . ?
N1 Ni1 N2 C18 1.0(5) . . . . ?
N1 Ni1 N4 C6 4.1(7) . . . . ?
N1 Ni1 N4 C9 -179.9(5) . . . . ?
N1 C1 C2 C3 0.4(8) . . . . ?
N1 C4 C5 C6 -2.8(10) . . . . ?
N1 C4 C5 C25 174.5(6) . . . . ?
N2 Ni1 N1 C1 0.3(6) . . . . ?
N2 Ni1 N1 C4 179.9(5) . . . . ?
N2 Ni1 N3 C10 179.7(5) . . . . ?
N2 Ni1 N3 C13 -3.6(6) . . . . ?
N2 C15 C16 C17 -1.5(7) . . . . ?
N3 Ni1 N2 C15 -1.6(5) . . . . ?
N3 Ni1 N2 C18 -179.2(5) . . . . ?
N3 Ni1 N4 C6 -175.8(7) . . . . ?
N3 Ni1 N4 C9 0.2(5) . . . . ?
N3 C10 C11 C12 -2.9(8) . . . . ?
N3 C13 C14 C15 -4.3(10) . . . . ?
N3 C13 C14 C34 175.3(6) . . . . ?
N4 Ni1 N1 C1 -179.3(5) . . . . ?
N4 Ni1 N1 C4 0.3(6) . . . . ?
N4 Ni1 N3 C10 -0.7(5) . . . . ?
N4 Ni1 N3 C13 176.0(6) . . . . ?
N4 C6 C7 N6 -176.2(7) . . . . ?
N4 C6 C7 C8 1.6(8) . . . . ?
N4 C9 C10 N3 -0.8(8) . . . . ?
N4 C9 C10 C11 -179.0(8) . . . . ?
N5 C1 C2 C3 -178.9(6) . . . . ?
N5 C19 C20 C21 176.5(6) . . . . ?
N5 C19 C24 C23 -175.7(7) . . . . ?
N6 C7 C8 C9 175.3(7) . . . . ?
N7 C12 C13 N3 173.2(7) . . . . ?
N7 C12 C13 C14 -12.0(13) . . . . ?
C1 N1 C4 C3 -1.0(7) . . . . ?
C1 N1 C4 C5 179.0(6) . . . . ?
C1 N5 C18 N2 1.7(10) . . . . ?
C1 N5 C18 C17 -177.3(6) . . . . ?
C1 N5 C19 C20 81.4(7) . . . . ?
C1 N5 C19 C24 -100.3(7) . . . . ?
C1 C2 C3 C4 -1.0(8) . . . . ?
C2 C3 C4 N1 1.3(8) . . . . ?
C2 C3 C4 C5 -178.7(7) . . . . ?
C3 C4 C5 C6 177.2(6) . . . . ?
C3 C4 C5 C25 -5.6(10) . . . . ?
C4 N1 C1 N5 179.7(6) . . . . ?
C4 N1 C1 C2 0.4(7) . . . . ?
C4 C5 C6 N4 6.7(10) . . . . ?
C4 C5 C6 C7 -179.4(7) . . . . ?
C4 C5 C25 C26 79.2(8) . . . . ?
C4 C5 C25 C30 -103.2(7) . . . . ?
C5 C6 C7 N6 9.2(14) . . . . ?
C5 C6 C7 C8 -172.9(8) . . . . ?
C5 C25 C26 C27 176.7(6) . . . . ?
C5 C25 C26 C31 0.2(10) . . . . ?
C5 C25 C30 C29 -177.8(6) . . . . ?
C5 C25 C30 C33 5.1(10) . . . . ?
C6 N4 C9 C8 -2.1(8) . . . . ?
C6 N4 C9 C10 177.2(6) . . . . ?
C6 C5 C25 C26 -103.5(7) . . . . ?
C6 C5 C25 C30 74.1(8) . . . . ?
C6 C7 C8 C9 -2.8(8) . . . . ?
C7 C8 C9 N4 3.0(8) . . . . ?
C7 C8 C9 C10 -176.0(8) . . . . ?
C8 C9 C10 N3 178.2(8) . . . . ?
C8 C9 C10 C11 0.0(16) . . . . ?
C9 N4 C6 C5 175.7(6) . . . . ?
C9 N4 C6 C7 0.3(8) . . . . ?
C9 C10 C11 C12 175.3(8) . . . . ?
C10 N3 C13 C12 -0.6(7) . . . . ?
C10 N3 C13 C14 -176.4(6) . . . . ?
C10 C11 C12 N7 -172.4(6) . . . . ?
C10 C11 C12 C13 2.6(8) . . . . ?
C11 C12 C13 N3 -1.3(8) . . . . ?
C11 C12 C13 C14 173.4(8) . . . . ?
C12 C13 C14 C15 -178.5(7) . . . . ?
C12 C13 C14 C34 1.2(12) . . . . ?
C13 N3 C10 C9 -176.5(6) . . . . ?
C13 N3 C10 C11 2.3(8) . . . . ?
C13 C14 C15 N2 -0.6(10) . . . . ?
C13 C14 C15 C16 179.7(6) . . . . ?
C13 C14 C34 C35 107.4(7) . . . . ?
C13 C14 C34 C39 -78.1(8) . . . . ?
C14 C15 C16 C17 178.2(6) . . . . ?
C14 C34 C35 C36 172.5(6) . . . . ?
C14 C34 C35 C40 -8.3(10) . . . . ?
C14 C34 C39 C38 -172.1(6) . . . . ?
C14 C34 C39 C42 6.1(10) . . . . ?
C15 N2 C18 N5 -179.9(6) . . . . ?
C15 N2 C18 C17 -0.8(7) . . . . ?
C15 C14 C34 C35 -73.0(8) . . . . ?
C15 C14 C34 C39 101.6(7) . . . . ?
C15 C16 C17 C18 1.0(8) . . . . ?
C16 C17 C18 N2 -0.1(8) . . . . ?
C16 C17 C18 N5 179.0(6) . . . . ?
C18 N2 C15 C14 -178.4(6) . . . . ?
C18 N2 C15 C16 1.4(6) . . . . ?
C18 N5 C1 N1 -0.3(10) . . . . ?
C18 N5 C1 C2 178.8(6) . . . . ?
C18 N5 C19 C20 -100.7(7) . . . . ?
C18 N5 C19 C24 77.6(7) . . . . ?
C19 N5 C1 N1 177.3(5) . . . . ?
C19 N5 C1 C2 -3.5(9) . . . . ?
C19 N5 C18 N2 -176.0(5) . . . . ?
C19 N5 C18 C17 5.0(9) . . . . ?
C19 C20 C21 C22 0.1(10) . . . . ?
C20 C19 C24 C23 2.5(11) . . . . ?
C20 C21 C22 Br1 -177.6(5) . . . . ?
C20 C21 C22 C23 0.7(11) . . . . ?
C21 C22 C23 C24 0.1(13) . . . . ?
C22 C23 C24 C19 -1.7(13) . . . . ?
C24 C19 C20 C21 -1.7(10) . . . . ?
C25 C5 C6 N4 -170.5(6) . . . . ?
C25 C5 C6 C7 3.4(12) . . . . ?
C25 C26 C27 C28 0.9(10) . . . . ?
C26 C25 C30 C29 -0.3(9) . . . . ?
C26 C25 C30 C33 -177.4(6) . . . . ?
C26 C27 C28 C29 0.0(11) . . . . ?
C26 C27 C28 C32 178.1(7) . . . . ?
C27 C28 C29 C30 -1.2(11) . . . . ?
C28 C29 C30 C25 1.3(10) . . . . ?
C28 C29 C30 C33 178.5(7) . . . . ?
C30 C25 C26 C27 -0.8(9) . . . . ?
C30 C25 C26 C31 -177.3(7) . . . . ?
C31 C26 C27 C28 177.6(7) . . . . ?
C32 C28 C29 C30 -179.2(7) . . . . ?
C34 C14 C15 N2 179.7(6) . . . . ?
C34 C14 C15 C16 0.1(10) . . . . ?
C34 C35 C36 C37 -0.7(11) . . . . ?
C35 C34 C39 C38 2.5(10) . . . . ?
C35 C34 C39 C42 -179.3(7) . . . . ?
C35 C36 C37 C38 3.1(11) . . . . ?
C35 C36 C37 C41 -176.1(7) . . . . ?
C36 C37 C38 C39 -2.6(11) . . . . ?
C37 C38 C39 C34 -0.1(11) . . . . ?
C37 C38 C39 C42 -178.4(7) . . . . ?
C39 C34 C35 C36 -2.1(9) . . . . ?
C39 C34 C35 C40 177.1(7) . . . . ?
C40 C35 C36 C37 -179.9(7) . . . . ?
C41 C37 C38 C39 176.5(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.956(15)
2 0.044(15)

