# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4c
_database_code_depnum_ccdc_archive 'CCDC 2338060'
loop_
_audit_author_name
_audit_author_address
'Mikhail Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2024-03-06 deposited with the CCDC.	2024-07-16 downloaded from the CCDC.
;
_audit_creation_date             2024-01-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H13 Cl F4 N2 Ni'
_chemical_formula_sum            'C20 H13 Cl F4 N2 Ni'
_chemical_formula_weight         451.48
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H13 Cl F4 N2 Ni'
_chemical_oxdiff_usercomment     TAR-84p
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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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'
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/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                   7.99026(4)
_cell_length_b                   19.21028(11)
_cell_length_c                   11.91822(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.8923(5)
_cell_angle_gamma                90
_cell_volume                     1796.430(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18527
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      80.1490
_cell_measurement_theta_min      3.7960
_shelx_estimated_absorpt_T_max   0.543
_shelx_estimated_absorpt_T_min   0.254
_exptl_absorpt_coefficient_mu    3.372
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.105
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.104a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             912
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 2 0.2873
-1 0 -2 0.1717
-2 5 -2 0.1779
1 1 -1 0.1373
-1 -1 1 0.1182
-2 0 5 0.1504
1 0 -1 0.1221
-1 0 1 0.1182
-3 1 5 0.1203
5 2 -2 0.1401
-1 5 -3 0.1671
1 -5 2 0.2386
-2 -1 -5 0.1767
0 -5 -1 0.2747
0 5 1 0.2849
1 -5 1 0.2346
1 -3 -5 0.1760
1 -1 -1 0.0936
-1 1 1 0.1127
5 -2 -3 0.1115
5 -2 -2 0.1097
-3 5 0 0.1606
3 -5 0 0.1666
0 -5 1 0.2470
1 5 2 0.2694

_exptl_crystal_size_max          0.559
_exptl_crystal_size_mid          0.440
_exptl_crystal_size_min          0.206
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0000 -0.0000 2.0000 -0.1633 -0.0574 -0.3122
-1.0000 0.0000 -2.0000 0.1633 0.0574 0.3122
-2.0000 5.0000 -2.0000 0.5893 0.1589 0.2255
1.0000 1.0000 -1.0000 -0.0626 0.2176 -0.0354
-1.0000 -1.0000 1.0000 0.0626 -0.2176 0.0354
-2.0000 -0.0000 5.0000 0.1992 -0.5898 -0.3195
1.0000 0.0000 -1.0000 -0.1208 0.1775 0.0024
-1.0000 -0.0000 1.0000 0.1208 -0.1775 -0.0024
-3.0000 1.0000 5.0000 0.3923 -0.6489 -0.2548
5.0000 2.0000 -2.0000 -0.5301 0.7329 -0.3781
-1.0000 5.0000 -3.0000 0.4685 0.3364 0.2280
1.0000 -5.0000 2.0000 -0.4543 -0.2581 -0.1231
-2.0000 -1.0000 -5.0000 0.2825 0.1528 0.7671
0.0000 -5.0000 -1.0000 -0.2769 -0.1225 0.2940
-0.0000 5.0000 1.0000 0.2769 0.1225 -0.2940
1.0000 -5.0000 1.0000 -0.4402 -0.1799 -0.0182
1.0000 -3.0000 -5.0000 -0.2389 0.3701 0.5354
1.0000 -1.0000 -1.0000 -0.1790 0.1373 0.0402
-1.0000 1.0000 1.0000 0.1790 -0.1373 -0.0402
5.0000 -2.0000 -3.0000 -0.7488 0.6506 -0.1220
5.0000 -2.0000 -2.0000 -0.7629 0.5723 -0.2269
-3.0000 5.0000 0.0000 0.6960 -0.0968 0.1182
3.0000 -5.0000 -0.0000 -0.6960 0.0968 -0.1182
0.0000 -5.0000 1.0000 -0.3052 -0.2791 0.0842
1.0000 5.0000 2.0000 0.1278 0.1434 -0.5013

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            24230
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.377
_diffrn_reflns_theta_min         4.424
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -1.00  68.00   0.50    0.05    --   15.16 -99.00-180.00  138
  2  ω     -1.00  68.00   0.50    0.05    --   15.16 -99.00-120.00  138
  3  ω    -21.00  61.00   0.50    0.05    --   15.16 -84.00 -25.00  164
  4  ω     34.00 112.00   0.50    0.20    --   71.20-125.00   0.00  156
  5  ω     43.00 108.00   0.50    0.25    --  127.25-111.00-180.00  130
  6  ω     37.00 105.00   0.50    0.25    --  127.25 -92.00-120.00  136
  7  ω     37.00 105.00   0.50    0.25    --  127.25 -92.00 -90.00  136
  8  ω     37.00 105.00   0.50    0.25    --  127.25 -92.00 -30.00  136
  9  ω     37.00 105.00   0.50    0.25    --  127.25 -92.00 -30.00  136
 10  ω     43.00 108.00   0.50    0.25    --  127.25-111.00  90.00  130
 11  ω     52.00  78.00   0.50    0.25    --  127.25 -92.00  30.00   52
 12  ω     38.00 174.00   0.50    0.25    --  127.25 -84.00 -25.00  272
 13  ω     38.00 174.00   0.50    0.25    --  127.25 -84.00 -25.00  272
 14  ω    -18.00 117.00   0.50    0.20    --   71.20 -84.00 -25.00  270
 15  ω     85.00 111.00   0.50    0.25    --  127.25 -80.00 102.37   52
 16  ω     41.00 105.00   0.50    0.25    --  127.25 -77.00 150.00  128
 17  ω     41.00 105.00   0.50    0.25    --  127.25 -77.00  90.00  128
 18  ω     49.00  76.00   0.50    0.25    --  127.25 -64.00  30.00   54
 19  ω     41.00 105.00   0.50    0.25    --  127.25 -77.00   0.00  128
 20  ω     -7.00  71.00   0.50    0.20    --   71.20 -61.00 150.00  156
 21  ω     49.00  76.00   0.50    0.25    --  127.25 -64.00   0.00   54
 22  ω     49.00  76.00   0.50    0.25    --  127.25 -64.00 -30.00   54
 23  ω     49.00  76.00   0.50    0.25    --  127.25 -64.00-120.00   54
 24  ω     49.00  75.00   0.50    0.25    --  127.25 -64.00-180.00   52
 25  ω    -17.00  35.00   0.50    0.20    --   71.20 -30.00 150.00  104
 26  ω     44.00 178.00   0.50    0.25    --  127.25  28.00  -3.64  268
 27  ω     90.00 178.00   0.50    0.25    --  127.25  64.00  90.00  176
 28  ω     84.00 178.00   0.50    0.25    --  127.25  77.00  60.00  188
 29  ω    104.00 130.00   0.50    0.25    --  127.25  50.00 150.00   52
 30  ω     90.00 178.00   0.50    0.25    --  127.25  64.00  30.00  176
 31  ω     90.00 178.00   0.50    0.25    --  127.25  64.00  30.00  176
 32  ω     90.00 177.00   0.50    0.25    --  127.25  64.00   0.00  174
 33  ω     77.00 178.00   0.50    0.25    --  127.25  38.00  30.00  202
 34  ω     44.00 178.00   0.50    0.25    --  127.25  28.00  -3.64  268
 35  ω     90.00 178.00   0.50    0.25    --  127.25  64.00-180.00  176
 36  ω     63.00 146.00   0.50    0.25    --  127.25 178.00 -30.00  166
 37  ω     63.00 146.00   0.50    0.25    --  127.25 178.00  90.00  166
 38  ω    103.00 178.00   0.50    0.25    --  127.25 111.00  60.00  150
 39  ω    102.00 153.00   0.50    0.20    --   71.20  84.00  94.00  102
 40  ω    101.00 178.00   0.50    0.25    --  127.25  84.00  94.00  154
 41  ω    128.00 169.00   0.50    0.25    --  127.25 111.00 -60.00   82
 42  ω     64.00 143.00   0.50    0.25    --  127.25 178.00-180.00  158
 43  ω    -25.00  11.00   0.50    0.20    --  -71.20  15.00-150.00   72
 44  ω   -110.00 -39.00   0.50    0.05    --  -15.16 178.00-180.00  142
 45  ω    -61.00  43.00   0.50    0.05    --  -15.16  84.00  94.00  208
 46  ω   -152.00 -23.00   0.50    0.25    -- -105.75  84.00  94.00  258
 47  ω    -82.00 -27.00   0.50    0.25    -- -105.75 111.00 150.00  110
 48  ω    -35.00  11.00   0.50    0.20    --  -71.20  30.00  60.00   92
 49  ω    -20.00  30.00   0.50    0.05    --  -15.16 -84.00 -25.00  100
 50  ω   -160.00 -79.00   0.50    0.20    --  -71.20 -84.00 -25.00  162
 51  ω   -177.00 -79.00   0.50    0.25    -- -105.75 -84.00 -25.00  196
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1349592000
_diffrn_orient_matrix_UB_12      0.0582161000
_diffrn_orient_matrix_UB_13      -0.0141500000
_diffrn_orient_matrix_UB_21      0.0992038000
_diffrn_orient_matrix_UB_22      0.0401556000
_diffrn_orient_matrix_UB_23      -0.0782809000
_diffrn_orient_matrix_UB_31      -0.1024467000
_diffrn_orient_matrix_UB_32      -0.0378206000
_diffrn_orient_matrix_UB_33      -0.1048699000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3907
_reflns_number_total             3931
_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 1.171.43.104a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.92a 64-bit (release 05-10-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.104a (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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.00311(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3931
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0274
_refine_ls_restrained_S_all      1.104
_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)+(0.0253P)²+1.3841P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0666
_refine_ls_wR_factor_ref         0.0668
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.55104(3) 0.36246(2) 0.72551(2) 0.01320(8) Uani 1 1 d . . . . .
Cl1 Cl 0.49188(4) 0.34868(2) 0.89667(3) 0.01997(9) Uani 1 1 d . . . . .
N1 N 0.89122(15) 0.41397(6) 0.80950(10) 0.0145(2) Uani 1 1 d . . . . .
C1 C 0.78620(18) 0.35922(7) 0.77626(12) 0.0141(3) Uani 1 1 d . . . . .
N2 N 0.89155(15) 0.30332(6) 0.79223(10) 0.0152(2) Uani 1 1 d . . . . .
C2 C 1.06030(18) 0.32282(8) 0.83369(13) 0.0178(3) Uani 1 1 d . . . . .
H2 H 1.148(3) 0.2911(10) 0.8489(16) 0.021 Uiso 1 1 d . U . . .
C3 C 1.06008(18) 0.39237(8) 0.84438(12) 0.0171(3) Uani 1 1 d . . . . .
H3 H 1.147(3) 0.4227(10) 0.8681(16) 0.021 Uiso 1 1 d . U . . .
C4 C 0.83734(17) 0.48511(7) 0.79626(12) 0.0150(3) Uani 1 1 d . . . . .
C5 C 0.86298(18) 0.52180(8) 0.70088(12) 0.0168(3) Uani 1 1 d . . . . .
F5 F 0.93912(13) 0.48934(5) 0.62375(8) 0.0265(2) Uani 1 1 d . . . . .
C6 C 0.81144(19) 0.59004(8) 0.68119(13) 0.0190(3) Uani 1 1 d . . . . .
H6 H 0.827(3) 0.6122(11) 0.6144(17) 0.023 Uiso 1 1 d . U . . .
C7 C 0.73369(19) 0.62087(8) 0.76286(13) 0.0197(3) Uani 1 1 d . . . . .
F7 F 0.68571(13) 0.68812(5) 0.74657(9) 0.0287(2) Uani 1 1 d . . . . .
C8 C 0.7035(2) 0.58678(8) 0.85874(14) 0.0220(3) Uani 1 1 d . . . . .
H8 H 0.648(3) 0.6094(11) 0.9104(18) 0.026 Uiso 1 1 d . U . . .
C9 C 0.75524(19) 0.51775(8) 0.87465(13) 0.0192(3) Uani 1 1 d . . . . .
H9 H 0.738(3) 0.4918(11) 0.9411(17) 0.023 Uiso 1 1 d . U . . .
C10 C 0.84071(17) 0.23387(7) 0.75815(12) 0.0150(3) Uani 1 1 d . . . . .
C11 C 0.87243(18) 0.20892(8) 0.65522(12) 0.0171(3) Uani 1 1 d . . . . .
F11 F 0.94680(13) 0.25165(5) 0.58944(8) 0.0296(2) Uani 1 1 d . . . . .
C12 C 0.82972(19) 0.14238(8) 0.61685(13) 0.0195(3) Uani 1 1 d . . . . .
H12 H 0.850(3) 0.1275(10) 0.5468(18) 0.023 Uiso 1 1 d . U . . .
C13 C 0.75163(19) 0.10122(8) 0.68622(13) 0.0189(3) Uani 1 1 d . . . . .
F13 F 0.70824(13) 0.03538(5) 0.65124(9) 0.0268(2) Uani 1 1 d . . . . .
C14 C 0.7148(2) 0.12352(9) 0.78855(14) 0.0247(3) Uani 1 1 d . . . . .
H14 H 0.659(3) 0.0921(11) 0.8331(18) 0.030 Uiso 1 1 d . U . . .
C15 C 0.7596(2) 0.19110(8) 0.82453(14) 0.0224(3) Uani 1 1 d . . . . .
H15 H 0.736(3) 0.2078(11) 0.8930(18) 0.027 Uiso 1 1 d . U . . .
C16 C 0.55908(19) 0.38399(9) 0.55966(12) 0.0204(3) Uani 1 1 d . . . . .
H16 H 0.664(3) 0.3906(11) 0.5354(17) 0.025 Uiso 1 1 d . U . . .
C17 C 0.4680(2) 0.31936(8) 0.55727(13) 0.0225(3) Uani 1 1 d . . . . .
H17 H 0.502(3) 0.2754(11) 0.5345(18) 0.027 Uiso 1 1 d . U . . .
C18 C 0.3245(2) 0.33288(9) 0.60371(13) 0.0241(3) Uani 1 1 d . . . . .
H18 H 0.246(3) 0.3003(11) 0.6180(18) 0.029 Uiso 1 1 d . U . . .
C19 C 0.3198(2) 0.40637(9) 0.62853(13) 0.0228(3) Uani 1 1 d . . . . .
H19 H 0.237(3) 0.4286(11) 0.6585(18) 0.027 Uiso 1 1 d . U . . .
C20 C 0.4588(2) 0.43837(8) 0.59590(13) 0.0204(3) Uani 1 1 d . . . . .
H20 H 0.487(3) 0.4860(11) 0.6020(17) 0.025 Uiso 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 Cl1 2.1953(4) . ?
Ni1 C1 1.8630(14) . ?
Ni1 C16 2.0323(15) . ?
Ni1 C17 2.1548(15) . ?
Ni1 C18 2.1710(15) . ?
Ni1 C19 2.1574(15) . ?
Ni1 C20 2.1507(15) . ?
N1 C1 1.3570(18) . ?
N1 C3 1.3977(18) . ?
N1 C4 1.4325(17) . ?
C1 N2 1.3555(18) . ?
N2 C2 1.3967(18) . ?
N2 C10 1.4310(18) . ?
C2 H2 0.92(2) . ?
C2 C3 1.342(2) . ?
C3 H3 0.91(2) . ?
C4 C5 1.385(2) . ?
C4 C9 1.389(2) . ?
C5 F5 1.3473(17) . ?
C5 C6 1.381(2) . ?
C6 H6 0.93(2) . ?
C6 C7 1.383(2) . ?
C7 F7 1.3511(17) . ?
C7 C8 1.377(2) . ?
C8 H8 0.93(2) . ?
C8 C9 1.391(2) . ?
C9 H9 0.97(2) . ?
C10 C11 1.384(2) . ?
C10 C15 1.384(2) . ?
C11 F11 1.3483(17) . ?
C11 C12 1.379(2) . ?
C12 H12 0.93(2) . ?
C12 C13 1.376(2) . ?
C13 F13 1.3562(17) . ?
C13 C14 1.376(2) . ?
C14 H14 0.97(2) . ?
C14 C15 1.393(2) . ?
C15 H15 0.93(2) . ?
C16 H16 0.94(2) . ?
C16 C17 1.437(2) . ?
C16 C20 1.432(2) . ?
C17 H17 0.94(2) . ?
C17 C18 1.388(2) . ?
C18 H18 0.92(2) . ?
C18 C19 1.444(2) . ?
C19 H19 0.91(2) . ?
C19 C20 1.388(2) . ?
C20 H20 0.94(2) . ?

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
C1 Ni1 Cl1 94.32(4) . . ?
C1 Ni1 C16 96.16(6) . . ?
C1 Ni1 C17 113.81(6) . . ?
C1 Ni1 C18 150.53(6) . . ?
C1 Ni1 C19 153.66(6) . . ?
C1 Ni1 C20 116.32(6) . . ?
C16 Ni1 Cl1 168.59(5) . . ?
C16 Ni1 C17 40.00(6) . . ?
C16 Ni1 C18 65.07(6) . . ?
C16 Ni1 C19 65.21(6) . . ?
C16 Ni1 C20 39.91(6) . . ?
C17 Ni1 Cl1 137.37(5) . . ?
C17 Ni1 C18 37.43(6) . . ?
C17 Ni1 C19 64.51(6) . . ?
C18 Ni1 Cl1 106.92(5) . . ?
C19 Ni1 Cl1 103.41(4) . . ?
C19 Ni1 C18 38.98(7) . . ?
C20 Ni1 Cl1 130.13(4) . . ?
C20 Ni1 C17 65.71(6) . . ?
C20 Ni1 C18 64.41(6) . . ?
C20 Ni1 C19 37.59(6) . . ?
C1 N1 C3 111.44(12) . . ?
C1 N1 C4 123.42(12) . . ?
C3 N1 C4 124.69(12) . . ?
N1 C1 Ni1 126.80(10) . . ?
N2 C1 Ni1 129.31(10) . . ?
N2 C1 N1 103.87(12) . . ?
C1 N2 C2 111.69(12) . . ?
C1 N2 C10 124.29(12) . . ?
C2 N2 C10 123.63(12) . . ?
N2 C2 H2 122.8(12) . . ?
C3 C2 N2 106.39(13) . . ?
C3 C2 H2 130.8(12) . . ?
N1 C3 H3 122.8(12) . . ?
C2 C3 N1 106.61(13) . . ?
C2 C3 H3 130.6(12) . . ?
C5 C4 N1 119.20(13) . . ?
C5 C4 C9 118.96(13) . . ?
C9 C4 N1 121.81(13) . . ?
F5 C5 C4 118.70(13) . . ?
F5 C5 C6 118.82(13) . . ?
C6 C5 C4 122.47(14) . . ?
C5 C6 H6 119.6(13) . . ?
C5 C6 C7 116.50(14) . . ?
C7 C6 H6 123.9(13) . . ?
F7 C7 C6 117.48(14) . . ?
F7 C7 C8 118.98(14) . . ?
C8 C7 C6 123.54(14) . . ?
C7 C8 H8 120.5(13) . . ?
C7 C8 C9 118.19(14) . . ?
C9 C8 H8 121.3(13) . . ?
C4 C9 C8 120.31(14) . . ?
C4 C9 H9 118.4(12) . . ?
C8 C9 H9 121.2(12) . . ?
C11 C10 N2 118.99(13) . . ?
C15 C10 N2 121.99(13) . . ?
C15 C10 C11 119.01(13) . . ?
F11 C11 C10 118.62(13) . . ?
F11 C11 C12 118.71(13) . . ?
C12 C11 C10 122.66(14) . . ?
C11 C12 H12 120.7(13) . . ?
C13 C12 C11 116.45(14) . . ?
C13 C12 H12 122.8(13) . . ?
C12 C13 C14 123.43(14) . . ?
F13 C13 C12 118.03(13) . . ?
F13 C13 C14 118.54(14) . . ?
C13 C14 H14 119.4(13) . . ?
C13 C14 C15 118.52(14) . . ?
C15 C14 H14 122.1(13) . . ?
C10 C15 C14 119.90(14) . . ?
C10 C15 H15 119.5(13) . . ?
C14 C15 H15 120.6(13) . . ?
Ni1 C16 H16 121.2(12) . . ?
C17 C16 Ni1 74.60(9) . . ?
C17 C16 H16 125.9(13) . . ?
C20 C16 Ni1 74.50(9) . . ?
C20 C16 H16 124.9(13) . . ?
C20 C16 C17 109.04(14) . . ?
Ni1 C17 H17 123.8(13) . . ?
C16 C17 Ni1 65.40(8) . . ?
C16 C17 H17 127.2(13) . . ?
C18 C17 Ni1 71.92(9) . . ?
C18 C17 C16 106.49(14) . . ?
C18 C17 H17 126.1(13) . . ?
Ni1 C18 H18 124.3(13) . . ?
C17 C18 Ni1 70.65(9) . . ?
C17 C18 H18 125.9(13) . . ?
C17 C18 C19 108.67(14) . . ?
C19 C18 Ni1 70.00(9) . . ?
C19 C18 H18 125.5(13) . . ?
Ni1 C19 H19 125.6(13) . . ?
C18 C19 Ni1 71.02(9) . . ?
C18 C19 H19 125.9(14) . . ?
C20 C19 Ni1 70.94(9) . . ?
C20 C19 C18 108.79(14) . . ?
C20 C19 H19 125.3(14) . . ?
Ni1 C20 H20 123.9(12) . . ?
C16 C20 Ni1 65.59(8) . . ?
C16 C20 H20 126.2(12) . . ?
C19 C20 Ni1 71.47(9) . . ?
C19 C20 C16 106.52(14) . . ?
C19 C20 H20 127.1(12) . . ?

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 C1 N2 C2 -178.79(11) . . . . ?
Ni1 C1 N2 C10 8.2(2) . . . . ?
Ni1 C16 C17 C18 60.56(11) . . . . ?
Ni1 C16 C20 C19 -60.09(11) . . . . ?
Ni1 C17 C18 C19 59.92(11) . . . . ?
Ni1 C18 C19 C20 61.19(11) . . . . ?
Ni1 C19 C20 C16 56.35(10) . . . . ?
Cl1 Ni1 C1 N1 -90.50(12) . . . . ?
Cl1 Ni1 C1 N2 87.28(13) . . . . ?
N1 C1 N2 C2 -0.62(15) . . . . ?
N1 C1 N2 C10 -173.60(12) . . . . ?
N1 C4 C5 F5 -0.4(2) . . . . ?
N1 C4 C5 C6 178.69(13) . . . . ?
N1 C4 C9 C8 -179.54(13) . . . . ?
C1 N1 C3 C2 -0.53(17) . . . . ?
C1 N1 C4 C5 -95.15(16) . . . . ?
C1 N1 C4 C9 82.83(18) . . . . ?
C1 N2 C2 C3 0.32(17) . . . . ?
C1 N2 C10 C11 97.13(17) . . . . ?
C1 N2 C10 C15 -82.36(19) . . . . ?
N2 C2 C3 N1 0.13(16) . . . . ?
N2 C10 C11 F11 -1.5(2) . . . . ?
N2 C10 C11 C12 179.08(13) . . . . ?
N2 C10 C15 C14 -179.07(14) . . . . ?
C2 N2 C10 C11 -75.03(18) . . . . ?
C2 N2 C10 C15 105.49(17) . . . . ?
C3 N1 C1 Ni1 178.93(10) . . . . ?
C3 N1 C1 N2 0.70(15) . . . . ?
C3 N1 C4 C5 76.58(18) . . . . ?
C3 N1 C4 C9 -105.45(17) . . . . ?
C4 N1 C1 Ni1 -8.37(19) . . . . ?
C4 N1 C1 N2 173.40(12) . . . . ?
C4 N1 C3 C2 -173.12(13) . . . . ?
C4 C5 C6 C7 0.8(2) . . . . ?
C5 C4 C9 C8 -1.6(2) . . . . ?
C5 C6 C7 F7 178.55(13) . . . . ?
C5 C6 C7 C8 -1.4(2) . . . . ?
F5 C5 C6 C7 179.88(13) . . . . ?
C6 C7 C8 C9 0.5(2) . . . . ?
C7 C8 C9 C4 1.0(2) . . . . ?
F7 C7 C8 C9 -179.40(14) . . . . ?
C9 C4 C5 F5 -178.46(13) . . . . ?
C9 C4 C5 C6 0.7(2) . . . . ?
C10 N2 C2 C3 173.35(13) . . . . ?
C10 C11 C12 C13 0.5(2) . . . . ?
C11 C10 C15 C14 1.4(2) . . . . ?
C11 C12 C13 F13 -179.84(13) . . . . ?
C11 C12 C13 C14 0.5(2) . . . . ?
F11 C11 C12 C13 -178.97(13) . . . . ?
C12 C13 C14 C15 -0.4(3) . . . . ?
C13 C14 C15 C10 -0.6(3) . . . . ?
F13 C13 C14 C15 179.90(14) . . . . ?
C15 C10 C11 F11 178.01(14) . . . . ?
C15 C10 C11 C12 -1.4(2) . . . . ?
C16 Ni1 C1 N1 84.99(13) . . . . ?
C16 Ni1 C1 N2 -97.24(13) . . . . ?
C16 C17 C18 Ni1 -56.40(10) . . . . ?
C16 C17 C18 C19 3.51(17) . . . . ?
C17 Ni1 C1 N1 122.38(12) . . . . ?
C17 Ni1 C1 N2 -59.85(14) . . . . ?
C17 C16 C20 Ni1 67.21(10) . . . . ?
C17 C16 C20 C19 7.13(17) . . . . ?
C17 C18 C19 Ni1 -60.32(11) . . . . ?
C17 C18 C19 C20 0.87(17) . . . . ?
C18 Ni1 C1 N1 132.86(13) . . . . ?
C18 Ni1 C1 N2 -49.4(2) . . . . ?
C18 C19 C20 Ni1 -61.24(10) . . . . ?
C18 C19 C20 C16 -4.89(17) . . . . ?
C19 Ni1 C1 N1 42.1(2) . . . . ?
C19 Ni1 C1 N2 -140.13(14) . . . . ?
C20 Ni1 C1 N1 48.83(14) . . . . ?
C20 Ni1 C1 N2 -133.39(13) . . . . ?
C20 C16 C17 Ni1 -67.15(10) . . . . ?
C20 C16 C17 C18 -6.60(17) . . . . ?

_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 1.154
_oxdiff_exptl_absorpt_empirical_full_min 0.865
####################################################################### 
# 
# 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_4b
_database_code_depnum_ccdc_archive 'CCDC 2348102'
loop_
_audit_author_name
_audit_author_address
'Mikhail Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2024-04-13 deposited with the CCDC.	2024-07-16 downloaded from the CCDC.
;
_audit_creation_date             2024-04-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H15 Cl F2 N2 Ni'
_chemical_formula_sum            'C20 H15 Cl F2 N2 Ni'
_chemical_formula_weight         415.50
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Ni Cl F2 N2 C20 H15'
_chemical_oxdiff_usercomment     TAR-96
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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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'
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/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                   10.82250(6)
_cell_length_b                   7.90636(4)
_cell_length_c                   20.14341(12)
_cell_angle_alpha                90
_cell_angle_beta                 95.3896(5)
_cell_angle_gamma                90
_cell_volume                     1715.982(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    22372
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.5740
_cell_measurement_theta_min      2.1920
_shelx_estimated_absorpt_T_max   0.558
_shelx_estimated_absorpt_T_min   0.391
_exptl_absorpt_coefficient_mu    3.298
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.223
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.117a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             848
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 -2 0.1236
0 -1 2 0.1156
0 0 -1 0.0990
0 0 1 0.1028
-1 2 -2 0.1323
1 -2 2 0.1350
-1 2 0 0.1650
0 -1 -1 0.1694
-1 2 1 0.1751
-1 0 2 0.1178
1 0 -2 0.1178
2 0 -1 0.1266
-2 0 1 0.1190
2 2 -1 0.1868
0 1 5 0.1241
1 -1 5 0.1021
-3 0 -5 0.1305
1 3 5 0.1597
3 -1 5 0.1124
-5 1 -1 0.1293
5 -1 1 0.1165
1 5 3 0.1640
-1 0 5 0.0972
1 -5 1 0.1562
-3 1 -11 0.1122

_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0000 1.0000 -2.0000 0.0017 -0.1811 0.1697
-0.0000 -1.0000 2.0000 -0.0017 0.1811 -0.1697
0.0000 -0.0000 -1.0000 0.0175 -0.0741 -0.0098
-0.0000 0.0000 1.0000 -0.0175 0.0741 0.0098
-1.0000 2.0000 -2.0000 0.1079 -0.1985 0.3862
1.0000 -2.0000 2.0000 -0.1079 0.1985 -0.3862
-1.0000 2.0000 0.0000 0.0729 -0.0502 0.4057
0.0000 -1.0000 -1.0000 0.0508 -0.0413 -0.1990
-1.0000 2.0000 1.0000 0.0554 0.0239 0.4155
-1.0000 0.0000 2.0000 0.1045 0.1637 0.0468
1.0000 -0.0000 -2.0000 -0.1045 -0.1637 -0.0468
2.0000 0.0000 -1.0000 -0.2615 -0.1050 -0.0643
-2.0000 -0.0000 1.0000 0.2615 0.1050 0.0643
2.0000 2.0000 -1.0000 -0.3281 -0.1707 0.3142
-0.0000 1.0000 5.0000 -0.1208 0.3379 0.2381
1.0000 -1.0000 5.0000 -0.1937 0.3881 -0.1677
-3.0000 -0.0000 -5.0000 0.5059 -0.3244 0.0330
1.0000 3.0000 5.0000 -0.3269 0.2568 0.5892
3.0000 -1.0000 5.0000 -0.4726 0.3572 -0.2222
-5.0000 1.0000 -1.0000 0.6816 -0.0298 0.3158
5.0000 -1.0000 1.0000 -0.6816 0.0298 -0.3158
1.0000 5.0000 3.0000 -0.3585 0.0429 0.9482
-1.0000 0.0000 5.0000 0.0520 0.3862 0.0761
1.0000 -5.0000 1.0000 0.0095 0.2228 -0.9636
-3.0000 1.0000 -11.0000 0.5776 -0.8021 0.1636

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            27642
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.065
_diffrn_reflns_theta_min         4.103
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     44.00 105.00   0.50    0.32    --  117.50 -77.00  90.00  122
  2  ω     44.00 105.00   0.50    0.32    --  117.50 -77.00 120.00  122
  3  ω     44.00 105.00   0.50    0.32    --  117.50 -77.00   0.00  122
  4  ω     44.00 105.00   0.50    0.32    --  117.50 -77.00  30.00  122
  5  ω     44.00  71.00   0.50    0.32    --  117.50 -61.00   0.00   54
  6  ω     44.00 105.00   0.50    0.32    --  117.50 -77.00 -60.00  122
  7  ω     44.00 105.00   0.50    0.32    --  117.50 -77.00-120.00  122
  8  ω     44.00 105.00   0.50    0.32    --  117.50 -77.00-180.00  122
  9  ω     44.00  69.00   0.50    0.32    --  117.50 -61.00-180.00   50
 10  ω    -34.00  43.00   0.50    0.09    --   42.78 -38.00-150.00  154
 11  ω     34.00  95.00   0.50    0.09    --   42.78-125.00-180.00  122
 12  ω     46.00 111.00   0.50    0.32    --  117.50-125.00 -30.00  130
 13  ω     49.00 104.00   0.50    0.32    --  117.50 -95.00   0.00  110
 14  ω     48.00  74.00   0.50    0.32    --  117.50 -95.00-120.00   52
 15  ω     44.00 105.00   0.50    0.32    --  117.50 -95.00-180.00  122
 16  ω     44.00 105.00   0.50    0.32    --  117.50 -95.00-150.00  122
 17  ω    115.00 151.00   0.50    0.32    --  117.50 -86.00 -98.77   72
 18  ω     44.00 149.00   0.50    0.32    --  117.50 -83.00 -42.45  210
 19  ω     44.00 149.00   0.50    0.32    --  117.50 -83.00 -42.45  210
 20  ω    121.00 147.00   0.50    0.32    --  117.50 -88.00  83.46   52
 21  ω     49.00 115.00   0.50    0.32    --  117.50 -88.00  83.46  132
 22  ω     44.00 150.00   0.50    0.32    --  117.50 -85.00 102.24  212
 23  ω     67.00 177.00   0.50    0.32    --  117.50  15.00 120.00  220
 24  ω     89.00 178.00   0.50    0.32    --  117.50  77.00 150.00  178
 25  ω     95.00 178.00   0.50    0.32    --  117.50  45.00 150.00  166
 26  ω     94.00 178.00   0.50    0.32    --  117.50  30.00 150.00  168
 27  ω    113.00 138.00   0.50    0.32    --  117.50  61.00  60.00   50
 28  ω    141.00 170.00   0.50    0.32    --  117.50  61.00  60.00   58
 29  ω     94.00 178.00   0.50    0.32    --  117.50  30.00  30.00  168
 30  ω     94.00 178.00   0.50    0.32    --  117.50  30.00  30.00  168
 31  ω      6.00 124.00   0.50    0.09    --   42.78  18.00 128.00  236
 32  ω     81.00 178.00   0.50    0.32    --  117.50  18.00 128.00  194
 33  ω     81.00 178.00   0.50    0.32    --  117.50  18.00 128.00  194
 34  ω    115.00 151.00   0.50    0.32    --  117.50  30.00 -90.00   72
 35  ω    118.00 144.00   0.50    0.32    --  117.50  45.00-180.00   52
 36  ω    130.00 156.00   0.50    0.32    --  117.50 125.00 -60.00   52
 37  ω     95.00 178.00   0.50    0.32    --  117.50 125.00   0.00  166
 38  ω     95.00 178.00   0.50    0.32    --  117.50 125.00   0.00  166
 39  ω   -123.00  -9.00   0.50    0.09    --  -42.78 -18.00 -39.00  228
 40  ω   -177.00 -62.00   0.50    0.32    --  -96.00 -18.00 -39.00  230
 41  ω    -71.00 -22.00   0.50    0.32    --  -96.00  61.00 -90.00   98
 42  ω    -27.00  38.00   0.50    0.09    --  -42.78  19.00-180.00  130
 43  ω    -51.00 -20.00   0.50    0.32    --  -96.00  45.00 -30.00   62
 44  ω    -26.00  38.00   0.50    0.09    --  -42.78  18.00 128.00  128
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1394813000
_diffrn_orient_matrix_UB_12      -0.0332961000
_diffrn_orient_matrix_UB_13      -0.0174970000
_diffrn_orient_matrix_UB_21      -0.0154353000
_diffrn_orient_matrix_UB_22      -0.0328231000
_diffrn_orient_matrix_UB_23      0.0741444000
_diffrn_orient_matrix_UB_31      -0.0272689000
_diffrn_orient_matrix_UB_32      0.1892272000
_diffrn_orient_matrix_UB_33      0.0097651000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3699
_reflns_number_total             3728
_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 1.171.43.117a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.117a 64-bit (release 26-03-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.117a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL  (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         3728
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0263
_refine_ls_restrained_S_all      1.072
_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)+(0.0257P)²+1.5319P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0648
_refine_ls_wR_factor_ref         0.0650
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.34124(2) 0.21857(3) 0.63689(2) 0.01222(7) Uani 1 1 d . . . . .
Cl1 Cl 0.30511(3) 0.12020(4) 0.53526(2) 0.01936(9) Uani 1 1 d . . . . .
N1 N 0.53733(10) 0.44559(15) 0.60147(6) 0.0123(2) Uani 1 1 d . . . . .
C1 C 0.41552(12) 0.42041(17) 0.61016(6) 0.0125(2) Uani 1 1 d . . . . .
N2 N 0.35979(11) 0.56706(15) 0.58804(6) 0.0130(2) Uani 1 1 d . . . . .
C2 C 0.44505(13) 0.68053(18) 0.56518(7) 0.0149(3) Uani 1 1 d . . . . .
H2 H 0.4199(18) 0.790(3) 0.5481(9) 0.019(5) Uiso 1 1 d . . . . .
C3 C 0.55661(13) 0.60410(18) 0.57383(7) 0.0146(3) Uani 1 1 d . . . . .
H3 H 0.6322(18) 0.640(2) 0.5620(9) 0.018(4) Uiso 1 1 d . . . . .
C4 C 0.63616(12) 0.33003(18) 0.62111(7) 0.0127(3) Uani 1 1 d . . . . .
C5 C 0.62823(13) 0.16096(18) 0.60215(7) 0.0149(3) Uani 1 1 d . . . . .
H5 H 0.5579(18) 0.122(2) 0.5744(9) 0.019(5) Uiso 1 1 d . . . . .
C6 C 0.72468(14) 0.05107(19) 0.62321(7) 0.0168(3) Uani 1 1 d . . . . .
H6 H 0.7226(17) -0.064(2) 0.6106(9) 0.016(4) Uiso 1 1 d . . . . .
C7 C 0.82566(13) 0.11519(19) 0.66222(7) 0.0176(3) Uani 1 1 d . . . . .
F7 F 0.91954(8) 0.00776(12) 0.68407(5) 0.0252(2) Uani 1 1 d . . . . .
C8 C 0.83628(14) 0.28278(19) 0.68050(7) 0.0179(3) Uani 1 1 d . . . . .
H8 H 0.9053(18) 0.322(2) 0.7066(9) 0.019(5) Uiso 1 1 d . . . . .
C9 C 0.73935(13) 0.39179(18) 0.65956(7) 0.0147(3) Uani 1 1 d . . . . .
H9 H 0.7435(18) 0.507(3) 0.6719(9) 0.020(5) Uiso 1 1 d . . . . .
C10 C 0.23013(13) 0.60459(17) 0.58859(7) 0.0143(3) Uani 1 1 d . . . . .
C11 C 0.17540(13) 0.58990(18) 0.64795(7) 0.0155(3) Uani 1 1 d . . . . .
H11 H 0.2238(17) 0.560(2) 0.6891(9) 0.016(4) Uiso 1 1 d . . . . .
C12 C 0.04943(14) 0.62452(18) 0.64896(8) 0.0173(3) Uani 1 1 d . . . . .
H12 H 0.0071(18) 0.615(2) 0.6894(10) 0.021(5) Uiso 1 1 d . . . . .
C13 C -0.01618(13) 0.67515(19) 0.59040(8) 0.0179(3) Uani 1 1 d . . . . .
F13 F -0.13946(8) 0.70468(12) 0.59146(5) 0.0246(2) Uani 1 1 d . . . . .
C14 C 0.03686(14) 0.6968(2) 0.53138(8) 0.0221(3) Uani 1 1 d . . . . .
H14 H -0.011(2) 0.732(3) 0.4924(12) 0.035(6) Uiso 1 1 d . . . . .
C15 C 0.16257(14) 0.6599(2) 0.53053(7) 0.0194(3) Uani 1 1 d . . . . .
H15 H 0.2027(19) 0.669(3) 0.4906(10) 0.027(5) Uiso 1 1 d . . . . .
C16 C 0.33863(14) 0.25394(19) 0.73840(7) 0.0165(3) Uani 1 1 d . . . . .
H16 H 0.3551(18) 0.358(3) 0.7604(9) 0.020(5) Uiso 1 1 d . . . . .
C17 C 0.21880(14) 0.1924(2) 0.71462(7) 0.0182(3) Uani 1 1 d . . . . .
H17 H 0.142(2) 0.254(3) 0.7168(11) 0.030(5) Uiso 1 1 d . . . . .
C18 C 0.23713(14) 0.03527(19) 0.68456(7) 0.0179(3) Uani 1 1 d . . . . .
H18 H 0.1741(19) -0.031(3) 0.6607(10) 0.027(5) Uiso 1 1 d . . . . .
C19 C 0.36683(14) -0.01101(18) 0.69698(7) 0.0171(3) Uani 1 1 d . . . . .
H19 H 0.4023(19) -0.111(3) 0.6817(10) 0.025(5) Uiso 1 1 d . . . . .
C20 C 0.42875(13) 0.12181(19) 0.73064(7) 0.0166(3) Uani 1 1 d . . . . .
H20 H 0.5150(19) 0.130(2) 0.7438(9) 0.019(5) Uiso 1 1 d . . . . .


_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 2.1905(4) . ?
Ni1 C1 1.8879(14) . ?
Ni1 C16 2.0666(14) . ?
Ni1 C17 2.1539(14) . ?
Ni1 C18 2.1201(14) . ?
Ni1 C19 2.1848(14) . ?
Ni1 C20 2.1708(14) . ?
N1 C1 1.3608(17) . ?
N1 C3 1.3949(18) . ?
N1 C4 1.4338(17) . ?
C1 N2 1.3624(18) . ?
N2 C2 1.3959(18) . ?
N2 C10 1.4353(17) . ?
C2 H2 0.96(2) . ?
C2 C3 1.347(2) . ?
C3 H3 0.92(2) . ?
C4 C5 1.391(2) . ?
C4 C9 1.3867(19) . ?
C5 H5 0.95(2) . ?
C5 C6 1.393(2) . ?
C6 H6 0.95(2) . ?
C6 C7 1.381(2) . ?
C7 F7 1.3651(16) . ?
C7 C8 1.377(2) . ?
C8 H8 0.92(2) . ?
C8 C9 1.392(2) . ?
C9 H9 0.94(2) . ?
C10 C11 1.388(2) . ?
C10 C15 1.390(2) . ?
C11 H11 0.966(18) . ?
C11 C12 1.392(2) . ?
C12 H12 0.98(2) . ?
C12 C13 1.378(2) . ?
C13 F13 1.3566(16) . ?
C13 C14 1.379(2) . ?
C14 H14 0.94(2) . ?
C14 C15 1.393(2) . ?
C15 H15 0.95(2) . ?
C16 H16 0.94(2) . ?
C16 C17 1.425(2) . ?
C16 C20 1.448(2) . ?
C17 H17 0.96(2) . ?
C17 C18 1.404(2) . ?
C18 H18 0.95(2) . ?
C18 C19 1.449(2) . ?
C19 H19 0.94(2) . ?
C19 C20 1.388(2) . ?
C20 H20 0.95(2) . ?

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
C1 Ni1 Cl1 94.42(4) . . ?
C1 Ni1 C16 102.33(6) . . ?
C1 Ni1 C17 126.58(6) . . ?
C1 Ni1 C18 164.93(6) . . ?
C1 Ni1 C19 145.60(6) . . ?
C1 Ni1 C20 112.54(6) . . ?
C16 Ni1 Cl1 162.73(4) . . ?
C16 Ni1 C17 39.40(6) . . ?
C16 Ni1 C18 65.62(6) . . ?
C16 Ni1 C19 64.98(6) . . ?
C16 Ni1 C20 39.86(5) . . ?
C17 Ni1 Cl1 125.25(4) . . ?
C17 Ni1 C19 64.67(6) . . ?
C17 Ni1 C20 65.28(6) . . ?
C18 Ni1 Cl1 97.16(4) . . ?
C18 Ni1 C17 38.35(6) . . ?
C18 Ni1 C19 39.31(6) . . ?
C18 Ni1 C20 64.67(6) . . ?
C19 Ni1 Cl1 103.00(4) . . ?
C20 Ni1 Cl1 135.47(4) . . ?
C20 Ni1 C19 37.16(6) . . ?
C1 N1 C3 111.46(11) . . ?
C1 N1 C4 125.30(12) . . ?
C3 N1 C4 123.16(11) . . ?
N1 C1 Ni1 127.15(10) . . ?
N1 C1 N2 103.77(11) . . ?
N2 C1 Ni1 128.71(10) . . ?
C1 N2 C2 111.64(11) . . ?
C1 N2 C10 125.21(12) . . ?
C2 N2 C10 123.14(12) . . ?
N2 C2 H2 121.5(12) . . ?
C3 C2 N2 106.34(12) . . ?
C3 C2 H2 132.2(12) . . ?
N1 C3 H3 123.3(12) . . ?
C2 C3 N1 106.79(12) . . ?
C2 C3 H3 129.7(12) . . ?
C5 C4 N1 120.76(12) . . ?
C9 C4 N1 118.07(12) . . ?
C9 C4 C5 121.17(13) . . ?
C4 C5 H5 119.8(12) . . ?
C4 C5 C6 119.38(13) . . ?
C6 C5 H5 120.8(12) . . ?
C5 C6 H6 121.4(11) . . ?
C7 C6 C5 118.32(14) . . ?
C7 C6 H6 120.3(11) . . ?
F7 C7 C6 118.70(13) . . ?
F7 C7 C8 118.14(13) . . ?
C8 C7 C6 123.17(14) . . ?
C7 C8 H8 121.0(12) . . ?
C7 C8 C9 118.23(13) . . ?
C9 C8 H8 120.8(12) . . ?
C4 C9 C8 119.71(13) . . ?
C4 C9 H9 120.2(12) . . ?
C8 C9 H9 120.1(12) . . ?
C11 C10 N2 119.07(12) . . ?
C11 C10 C15 121.17(13) . . ?
C15 C10 N2 119.72(13) . . ?
C10 C11 H11 121.2(11) . . ?
C10 C11 C12 119.59(13) . . ?
C12 C11 H11 119.2(11) . . ?
C11 C12 H12 122.3(11) . . ?
C13 C12 C11 118.10(14) . . ?
C13 C12 H12 119.6(11) . . ?
C12 C13 C14 123.47(14) . . ?
F13 C13 C12 117.71(13) . . ?
F13 C13 C14 118.82(13) . . ?
C13 C14 H14 121.2(15) . . ?
C13 C14 C15 118.09(14) . . ?
C15 C14 H14 120.7(15) . . ?
C10 C15 C14 119.51(14) . . ?
C10 C15 H15 119.2(13) . . ?
C14 C15 H15 121.3(13) . . ?
Ni1 C16 H16 124.3(12) . . ?
C17 C16 Ni1 73.60(8) . . ?
C17 C16 H16 125.5(12) . . ?
C17 C16 C20 108.56(13) . . ?
C20 C16 Ni1 73.95(8) . . ?
C20 C16 H16 125.5(12) . . ?
Ni1 C17 H17 125.0(13) . . ?
C16 C17 Ni1 66.99(8) . . ?
C16 C17 H17 124.8(13) . . ?
C18 C17 Ni1 69.52(8) . . ?
C18 C17 C16 106.62(13) . . ?
C18 C17 H17 128.5(13) . . ?
Ni1 C18 H18 122.3(12) . . ?
C17 C18 Ni1 72.13(8) . . ?
C17 C18 H18 125.5(13) . . ?
C17 C18 C19 108.82(13) . . ?
C19 C18 Ni1 72.75(8) . . ?
C19 C18 H18 125.7(13) . . ?
Ni1 C19 H19 123.3(12) . . ?
C18 C19 Ni1 67.93(8) . . ?
C18 C19 H19 124.9(13) . . ?
C20 C19 Ni1 70.87(8) . . ?
C20 C19 C18 107.98(13) . . ?
C20 C19 H19 127.0(13) . . ?
Ni1 C20 H20 123.7(12) . . ?
C16 C20 Ni1 66.19(8) . . ?
C16 C20 H20 125.1(12) . . ?
C19 C20 Ni1 71.97(8) . . ?
C19 C20 C16 107.43(13) . . ?
C19 C20 H20 127.4(12) . . ?

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 C1 N2 C2 -172.53(10) . . . . ?
Ni1 C1 N2 C10 8.4(2) . . . . ?
Ni1 C16 C17 C18 58.43(10) . . . . ?
Ni1 C16 C20 C19 -60.45(10) . . . . ?
Ni1 C17 C18 C19 63.96(10) . . . . ?
Ni1 C18 C19 C20 59.78(10) . . . . ?
Ni1 C19 C20 C16 56.83(10) . . . . ?
Cl1 Ni1 C1 N1 -88.22(12) . . . . ?
Cl1 Ni1 C1 N2 83.64(12) . . . . ?
N1 C1 N2 C2 0.79(15) . . . . ?
N1 C1 N2 C10 -178.29(12) . . . . ?
N1 C4 C5 C6 -178.66(12) . . . . ?
N1 C4 C9 C8 178.95(12) . . . . ?
C1 N1 C3 C2 0.24(16) . . . . ?
C1 N1 C4 C5 51.51(19) . . . . ?
C1 N1 C4 C9 -128.36(14) . . . . ?
C1 N2 C2 C3 -0.67(16) . . . . ?
C1 N2 C10 C11 53.84(19) . . . . ?
C1 N2 C10 C15 -128.18(15) . . . . ?
N2 C2 C3 N1 0.25(15) . . . . ?
N2 C10 C11 C12 -179.43(13) . . . . ?
N2 C10 C15 C14 -179.77(14) . . . . ?
C2 N2 C10 C11 -125.14(15) . . . . ?
C2 N2 C10 C15 52.84(19) . . . . ?
C3 N1 C1 Ni1 172.84(10) . . . . ?
C3 N1 C1 N2 -0.62(14) . . . . ?
C3 N1 C4 C5 -132.06(14) . . . . ?
C3 N1 C4 C9 48.07(18) . . . . ?
C4 N1 C1 Ni1 -10.38(19) . . . . ?
C4 N1 C1 N2 176.16(12) . . . . ?
C4 N1 C3 C2 -176.63(12) . . . . ?
C4 C5 C6 C7 -0.3(2) . . . . ?
C5 C4 C9 C8 -0.9(2) . . . . ?
C5 C6 C7 F7 178.83(13) . . . . ?
C5 C6 C7 C8 -0.9(2) . . . . ?
C6 C7 C8 C9 1.2(2) . . . . ?
C7 C8 C9 C4 -0.3(2) . . . . ?
F7 C7 C8 C9 -178.55(13) . . . . ?
C9 C4 C5 C6 1.2(2) . . . . ?
C10 N2 C2 C3 178.43(12) . . . . ?
C10 C11 C12 C13 -1.0(2) . . . . ?
C11 C10 C15 C14 -1.8(2) . . . . ?
C11 C12 C13 F13 178.44(13) . . . . ?
C11 C12 C13 C14 -1.5(2) . . . . ?
C12 C13 C14 C15 2.2(2) . . . . ?
C13 C14 C15 C10 -0.5(2) . . . . ?
F13 C13 C14 C15 -177.67(14) . . . . ?
C15 C10 C11 C12 2.6(2) . . . . ?
C16 Ni1 C1 N1 96.04(12) . . . . ?
C16 Ni1 C1 N2 -92.11(13) . . . . ?
C16 C17 C18 Ni1 -56.84(10) . . . . ?
C16 C17 C18 C19 7.11(16) . . . . ?
C17 Ni1 C1 N1 130.68(11) . . . . ?
C17 Ni1 C1 N2 -57.47(14) . . . . ?
C17 C16 C20 Ni1 66.02(10) . . . . ?
C17 C16 C20 C19 5.56(16) . . . . ?
C17 C18 C19 Ni1 -63.56(10) . . . . ?
C17 C18 C19 C20 -3.77(16) . . . . ?
C18 Ni1 C1 N1 131.6(2) . . . . ?
C18 Ni1 C1 N2 -56.5(3) . . . . ?
C18 C19 C20 Ni1 -57.95(10) . . . . ?
C18 C19 C20 C16 -1.12(16) . . . . ?
C19 Ni1 C1 N1 32.59(18) . . . . ?
C19 Ni1 C1 N2 -155.56(11) . . . . ?
C20 Ni1 C1 N1 55.51(13) . . . . ?
C20 Ni1 C1 N2 -132.64(12) . . . . ?
C20 C16 C17 Ni1 -66.24(10) . . . . ?
C20 C16 C17 C18 -7.81(16) . . . . ?

_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 1.176
_oxdiff_exptl_absorpt_empirical_full_min 0.901
####################################################################### 
# 
# 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_4e
_database_code_depnum_ccdc_archive 'CCDC 2338062'
loop_
_audit_author_name
_audit_author_address
'Mikhail Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2024-03-06 deposited with the CCDC.	2024-07-16 downloaded from the CCDC.
;
_audit_creation_date             2024-03-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H13 Cl F4 N2 Ni'
_chemical_formula_sum            'C20 H13 Cl F4 N2 Ni'
_chemical_formula_weight         451.48
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H13N2F4ClNi
_chemical_oxdiff_usercomment     TAR-87_tarabrin
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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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'
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                   7.95480(7)
_cell_length_b                   17.60556(13)
_cell_length_c                   13.33453(10)
_cell_angle_alpha                90
_cell_angle_beta                 106.8036(9)
_cell_angle_gamma                90
_cell_volume                     1787.74(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    22210
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.7440
_cell_measurement_theta_min      2.5100
_shelx_estimated_absorpt_T_max   0.773
_shelx_estimated_absorpt_T_min   0.687
_exptl_absorpt_coefficient_mu    3.389
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.695
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.104a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear intense red'
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             912
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0538
2 -5 -1 0.0544
0 1 -2 0.0680
-1 2 0 0.0540
1 5 1 0.0552
-1 2 -1 0.0595
-1 -5 -1 0.0494
0 1 0 0.0522
0 5 -2 0.0506
1 -5 -2 0.0460
2 2 -1 0.0456
-2 -1 -1 0.0538
0 -2 -1 0.0481
-1 -5 3 0.0467
0 5 2 0.0532
5 3 0 0.0469
-4 -5 0 0.0452
-1 2 1 0.0459
1 -2 -2 0.0420
1 5 -4 0.0472
2 -1 -2 0.0361
-1 0 1 0.0365
0 -1 2 0.0425

_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0002 -1.0003 0.0003 0.0771 0.0097 -0.0404
2.0000 -5.0008 -0.9998 0.3666 -0.3186 -0.3248
0.0013 1.0033 -1.9995 0.0364 -0.0848 0.2395
-0.9999 2.0010 0.0003 -0.1164 0.1454 0.1920
1.0011 4.9993 0.9971 -0.4797 -0.1756 -0.0091
-0.9993 2.0025 -0.9993 -0.0597 0.1078 0.2916
-1.0011 -4.9993 -0.9971 0.4797 0.1756 0.0091
0.0002 1.0003 -0.0003 -0.0771 -0.0097 0.0404
0.0023 5.0044 -2.0008 -0.2718 -0.1236 0.4009
1.0002 -4.9987 -1.9985 0.4611 -0.1914 -0.1139
2.0017 2.0011 -1.0020 -0.1728 -0.3864 -0.0423
-2.0004 -0.9978 -0.9974 0.2092 0.3016 0.2818
0.0000 -1.9990 -0.9989 0.2109 -0.0182 0.0189
-1.0031 -5.0055 3.0012 0.2528 0.3259 -0.3892
0.0002 4.9983 1.9976 -0.4988 0.0267 0.0026
5.0025 2.9984 -0.0055 -0.4197 -0.8528 -0.4354
-4.0026 -4.9995 0.0052 0.5361 0.7074 0.2434
-1.0004 1.9995 0.9999 -0.1731 0.1829 0.0924
1.0009 -1.9979 -1.9994 0.2299 -0.2205 0.0071
1.0037 5.0070 -4.0008 -0.1960 -0.3635 0.4888
2.0015 -0.9981 -2.0007 0.1151 -0.3949 -0.0638
-1.0009 -0.0011 1.0005 -0.0190 0.2023 0.0117
-0.0013 -1.0033 1.9995 -0.0364 0.0848 -0.2395

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_unetI/netI     0.0096
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            28249
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.980
_diffrn_reflns_theta_min         4.278
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     21.00 119.00   0.50    0.50    --   42.78  45.00-137.00  196
  2  ω     21.00 119.00   0.50    0.50    --   42.78  45.00-137.00  196
  3  ω    -80.00 -22.00   0.50    1.80    --  -96.00  99.00 -39.00  116
  4  ω    -51.00 -20.00   0.50    1.80    --  -96.00  45.00-137.00   62
  5  ω     44.00 106.00   0.50    1.80    --  117.50 -99.00-145.00  124
  6  ω     95.00 178.00   0.50    1.80    --  117.50  45.00-137.00  166
  7  ω    101.00 178.00   0.50    1.80    --  117.50  86.00  66.00  154
  8  ω    -76.00  31.00   0.50    0.50    --  -42.78  86.00  66.00  214
  9  ω    -37.00  27.00   0.50    0.50    --   42.78 -19.00 -60.00  128
 10  ω    -51.00 -20.00   0.50    1.80    --  -96.00  45.00  60.00   62
 11  ω     46.00 111.00   0.50    1.80    --  117.50-125.00 -60.00  130
 12  ω     44.00  71.00   0.50    1.80    --  117.50 -61.00  30.00   54
 13  ω     95.00 178.00   0.50    1.80    --  117.50 125.00  90.00  166
 14  ω     89.00 178.00   0.50    1.80    --  117.50  77.00 -60.00  178
 15  ω      0.00  37.00   0.50    0.50    --   42.81 -85.00 -52.00   74
 16  ω      2.00  28.00   0.50    0.50    --  -42.81  19.00  30.00   52
 17  ω    -86.00 -48.00   0.50    0.50    --  -42.81 -77.00 -90.00   76
 18  ω   -114.00 -87.00   0.50    0.50    --  -42.81 -77.00 -90.00   54
 19  ω    -29.00  27.00   0.50    0.50    --   42.81 -19.00  60.00  112
 20  ω     65.00  91.00   0.50    0.50    --   42.81-125.00-150.00   52
 21  ω     36.00  62.00   0.50    0.50    --   42.81-125.00-150.00   52
 22  ω     40.00  89.00   0.50    0.50    --   42.81-125.00 150.00   98
 23  ω    -49.00 -21.00   0.50    1.80    --  -96.00  45.00  30.00   56
 24  ω    -51.00 -22.00   0.50    1.80    --  -96.00  45.00 -90.00   58
 25  ω     45.00  70.00   0.50    1.80    --  117.50 -61.00-150.00   50
 26  ω     76.00 111.00   0.50    1.80    --  117.50-125.00-150.00   70
 27  ω     46.00  77.00   0.50    1.80    --  117.50 -77.00 120.00   62
 28  ω     51.00  78.00   0.50    1.80    --  117.50 -77.00 150.00   54
 29  ω     96.00 139.00   0.50    1.80    --  117.50  30.00  60.00   86
 30  ω     49.00  74.00   0.50    1.80    --  117.50-125.00-150.00   50
 31  ω    109.00 135.00   0.50    1.80    --  117.50  30.00  30.00   52
 32  ω    107.00 155.00   0.50    1.80    --  117.50  77.00  90.00   96
 33  ω    107.00 168.00   0.50    1.80    --  117.50  77.00 -30.00  122
 34  ω     77.00 111.00   0.50    1.80    --  117.50-125.00  60.00   68
 35  ω     73.00 111.00   0.50    1.80    --  117.50-125.00  30.00   76
 36  ω     60.00  90.00   0.50    1.80    --  117.50 -82.00  40.45   60
 37  ω     84.00 110.00   0.50    1.80    --  117.50-125.00 -30.00   52
 38  ω     93.00 118.00   0.50    1.80    --  117.50 -87.00-105.83   50
 39  ω    132.00 168.00   0.50    1.80    --  117.50 125.00  30.00   72
 40  ω     77.00 111.00   0.50    1.80    --  117.50-125.00-120.00   68
 41  ω     50.00 101.00   0.50    1.80    --  117.50 -77.00  60.00  102
 42  ω     69.00  95.00   0.50    1.80    --  117.50 -85.00 -52.00   52
 43  ω     45.00  71.00   0.50    1.80    --  117.50 -61.00 -30.00   52
 44  ω    108.00 133.00   0.50    1.80    --  117.50  30.00 150.00   50
 45  ω   -167.00-141.00   0.50    1.80    --  -96.00 -85.00 -52.00   52
 46  ω     44.00  69.00   0.50    1.80    --  117.50 -61.00  90.00   50
 47  ω     47.00  94.00   0.50    1.80    --  117.50 -95.00 150.00   94
 48  ω     53.00  79.00   0.50    1.80    --  117.50 -77.00 -90.00   52
 49  ω    118.00 149.00   0.50    1.80    --  117.50  61.00  90.00   62
 50  ω    136.00 178.00   0.50    1.80    --  117.50  45.00 150.00   84
 51  ω     56.00  95.00   0.50    1.80    --  117.50 -95.00   0.00   78
 52  ω     83.00 109.00   0.50    1.80    --  117.50 -78.00 -52.45   52
 53  ω    116.00 155.00   0.50    1.80    --  117.50 125.00 -60.00   78
 54  ω    131.00 157.00   0.50    1.80    --  117.50  77.00   0.00   52
 55  ω     68.00  97.00   0.50    1.80    --  117.50 -77.00  90.00   58
 56  ω     61.00 105.00   0.50    1.80    --  117.50 -85.00   3.73   88
 57  ω     44.00  69.00   0.50    1.80    --  117.50 -61.00   0.00   50
 58  ω   -116.00 -20.00   0.50    0.50    --  -42.81 -57.00 -30.00  192
 59  ω   -116.00 -20.00   0.50    0.50    --  -42.81 -57.00  60.00  192
 60  ω    -37.00  27.00   0.50    0.50    --   42.81 -19.00-180.00  128
 61  ω     14.00 117.00   0.50    0.50    --   42.81  77.00 -90.00  206
 62  ω     14.00 117.00   0.50    0.50    --   42.81  77.00  90.00  206
 63  ω     14.00  78.00   0.50    0.50    --   42.81  77.00-180.00  128
 64  ω      9.00  43.00   0.50    0.50    --   42.81  89.00  14.22   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0377883000
_diffrn_orient_matrix_UB_12      -0.0770443000
_diffrn_orient_matrix_UB_13      -0.0569079000
_diffrn_orient_matrix_UB_21      -0.1646554000
_diffrn_orient_matrix_UB_22      -0.0096375000
_diffrn_orient_matrix_UB_23      0.0374890000
_diffrn_orient_matrix_UB_31      -0.1113276000
_diffrn_orient_matrix_UB_32      0.0403415000
_diffrn_orient_matrix_UB_33      -0.0996154000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3779
_reflns_number_total             3890
_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 1.171.43.104a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.104a 64-bit (release 22-12-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.104a (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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         3890
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0246
_refine_ls_R_factor_gt           0.0241
_refine_ls_restrained_S_all      1.059
_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)+(0.0315P)²+1.0770P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0653
_refine_ls_wR_factor_ref         0.0657
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.67790(3) 0.65048(2) 0.21390(2) 0.01312(7) Uani 1 1 d . . . . .
Cl1 Cl 0.87554(4) 0.65815(2) 0.36645(3) 0.03042(10) Uani 1 1 d . . . . .
N1 N 0.41256(13) 0.59237(6) 0.30394(8) 0.0142(2) Uani 1 1 d . . . . .
C1 C 0.49140(16) 0.65255(6) 0.27228(9) 0.0132(2) Uani 1 1 d . . . . .
N2 N 0.40691(13) 0.71346(6) 0.29730(8) 0.0135(2) Uani 1 1 d . . . . .
C2 C 0.27767(17) 0.69172(7) 0.34294(10) 0.0176(2) Uani 1 1 d . . . . .
H2 H 0.207(2) 0.7267(10) 0.3632(13) 0.021 Uiso 1 1 d . U . . .
C3 C 0.28055(17) 0.61561(7) 0.34691(10) 0.0181(2) Uani 1 1 d . . . . .
H3 H 0.212(2) 0.5820(10) 0.3702(13) 0.022 Uiso 1 1 d . U . . .
C4 C 0.45266(16) 0.51504(7) 0.28909(10) 0.0148(2) Uani 1 1 d . . . . .
C5 C 0.36939(17) 0.47731(7) 0.19650(10) 0.0166(2) Uani 1 1 d . . . . .
F5 F 0.24976(11) 0.51648(4) 0.12199(6) 0.02332(17) Uani 1 1 d . . . . .
C6 C 0.40663(18) 0.40287(7) 0.17847(10) 0.0191(3) Uani 1 1 d . . . . .
H6 H 0.351(2) 0.3811(10) 0.1164(14) 0.023 Uiso 1 1 d . U . . .
C7 C 0.53189(19) 0.36445(7) 0.25610(11) 0.0211(3) Uani 1 1 d . . . . .
H7 H 0.563(2) 0.3127(10) 0.2433(14) 0.025 Uiso 1 1 d . U . . .
C8 C 0.61519(18) 0.39933(7) 0.35091(11) 0.0220(3) Uani 1 1 d . . . . .
H8 H 0.701(2) 0.3752(11) 0.4040(14) 0.026 Uiso 1 1 d . U . . .
C9 C 0.57372(17) 0.47400(7) 0.36556(10) 0.0182(2) Uani 1 1 d . . . . .
F9 F 0.65288(11) 0.50900(4) 0.45686(6) 0.02572(18) Uani 1 1 d . . . . .
C10 C 0.44174(15) 0.78996(7) 0.27472(9) 0.0140(2) Uani 1 1 d . . . . .
C11 C 0.37764(17) 0.81933(7) 0.17449(10) 0.0172(2) Uani 1 1 d . . . . .
F11 F 0.27634(11) 0.77395(5) 0.10053(6) 0.02569(18) Uani 1 1 d . . . . .
C12 C 0.41427(18) 0.89227(7) 0.14875(10) 0.0204(3) Uani 1 1 d . . . . .
H12 H 0.372(2) 0.9077(10) 0.0782(14) 0.024 Uiso 1 1 d . U . . .
C13 C 0.51470(18) 0.93840(7) 0.22797(11) 0.0205(3) Uani 1 1 d . . . . .
H13 H 0.543(2) 0.9889(10) 0.2114(13) 0.025 Uiso 1 1 d . U . . .
C14 C 0.57480(18) 0.91233(7) 0.33083(11) 0.0208(3) Uani 1 1 d . . . . .
H14 H 0.640(2) 0.9426(10) 0.3848(14) 0.025 Uiso 1 1 d . U . . .
C15 C 0.53765(17) 0.83854(7) 0.35201(10) 0.0168(2) Uani 1 1 d . . . . .
F15 F 0.59299(11) 0.81241(4) 0.45082(6) 0.02463(18) Uani 1 1 d . . . . .
C16 C 0.53102(18) 0.63803(8) 0.06222(10) 0.0185(2) Uani 1 1 d . . . . .
H16 H 0.411(2) 0.6337(10) 0.0441(13) 0.022 Uiso 1 1 d . U . . .
C17 C 0.62980(19) 0.70644(7) 0.06254(10) 0.0206(3) Uani 1 1 d . . . . .
H17 H 0.582(2) 0.7565(10) 0.0460(13) 0.025 Uiso 1 1 d . U . . .
C18 C 0.80630(18) 0.68692(7) 0.09578(10) 0.0186(2) Uani 1 1 d . . . . .
H18 H 0.902(2) 0.7188(10) 0.1071(13) 0.022 Uiso 1 1 d . U . . .
C19 C 0.82009(17) 0.60539(7) 0.11039(9) 0.0162(2) Uani 1 1 d . . . . .
H19 H 0.925(2) 0.5792(10) 0.1332(13) 0.019 Uiso 1 1 d . U . . .
C20 C 0.65047(17) 0.57502(7) 0.08450(10) 0.0168(2) Uani 1 1 d . . . . .
H20 H 0.617(2) 0.5231(10) 0.0851(13) 0.020 Uiso 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 Cl1 2.1860(4) . ?
Ni1 C1 1.8644(13) . ?
Ni1 C16 2.0342(13) . ?
Ni1 C17 2.1781(13) . ?
Ni1 C18 2.2059(12) . ?
Ni1 C19 2.1719(12) . ?
Ni1 C20 2.1383(12) . ?
N1 C1 1.3591(15) . ?
N1 C3 1.3952(16) . ?
N1 C4 1.4251(15) . ?
C1 N2 1.3575(15) . ?
N2 C2 1.3912(16) . ?
N2 C10 1.4246(15) . ?
C2 H2 0.927(17) . ?
C2 C3 1.3410(19) . ?
C3 H3 0.918(18) . ?
C4 C5 1.3898(17) . ?
C4 C9 1.3861(18) . ?
C5 F5 1.3497(15) . ?
C5 C6 1.3799(18) . ?
C6 H6 0.903(18) . ?
C6 C7 1.388(2) . ?
C7 H7 0.971(18) . ?
C7 C8 1.389(2) . ?
C8 H8 0.930(19) . ?
C8 C9 1.3830(18) . ?
C9 F9 1.3473(15) . ?
C10 C11 1.3855(17) . ?
C10 C15 1.3860(17) . ?
C11 F11 1.3419(14) . ?
C11 C12 1.3818(18) . ?
C12 H12 0.942(17) . ?
C12 C13 1.3878(19) . ?
C13 H13 0.959(18) . ?
C13 C14 1.3933(19) . ?
C14 H14 0.925(18) . ?
C14 C15 1.3796(18) . ?
C15 F15 1.3439(14) . ?
C16 H16 0.922(18) . ?
C16 C17 1.4373(19) . ?
C16 C20 1.4347(18) . ?
C17 H17 0.959(17) . ?
C17 C18 1.3878(19) . ?
C18 H18 0.925(18) . ?
C18 C19 1.4485(17) . ?
C19 H19 0.924(17) . ?
C19 C20 1.3986(17) . ?
C20 H20 0.952(17) . ?

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
Cl1 Ni1 C18 106.83(4) . . ?
C1 Ni1 Cl1 93.17(4) . . ?
C1 Ni1 C16 96.87(5) . . ?
C1 Ni1 C17 115.48(5) . . ?
C1 Ni1 C18 151.77(5) . . ?
C1 Ni1 C19 153.63(5) . . ?
C1 Ni1 C20 116.18(5) . . ?
C16 Ni1 Cl1 169.66(4) . . ?
C16 Ni1 C17 39.72(5) . . ?
C16 Ni1 C18 64.71(5) . . ?
C16 Ni1 C19 65.40(5) . . ?
C16 Ni1 C20 40.13(5) . . ?
C17 Ni1 Cl1 136.12(4) . . ?
C17 Ni1 C18 36.90(5) . . ?
C19 Ni1 Cl1 104.32(4) . . ?
C19 Ni1 C17 63.94(5) . . ?
C19 Ni1 C18 38.63(5) . . ?
C20 Ni1 Cl1 131.87(4) . . ?
C20 Ni1 C17 65.39(5) . . ?
C20 Ni1 C18 64.20(5) . . ?
C20 Ni1 C19 37.86(5) . . ?
C1 N1 C3 111.63(10) . . ?
C1 N1 C4 124.03(10) . . ?
C3 N1 C4 124.23(10) . . ?
N1 C1 Ni1 127.50(9) . . ?
N2 C1 Ni1 128.93(9) . . ?
N2 C1 N1 103.52(10) . . ?
C1 N2 C2 111.79(10) . . ?
C1 N2 C10 123.68(10) . . ?
C2 N2 C10 124.47(10) . . ?
N2 C2 H2 122.3(10) . . ?
C3 C2 N2 106.61(11) . . ?
C3 C2 H2 131.1(11) . . ?
N1 C3 H3 122.8(11) . . ?
C2 C3 N1 106.44(11) . . ?
C2 C3 H3 130.7(11) . . ?
C5 C4 N1 120.77(11) . . ?
C9 C4 N1 122.11(11) . . ?
C9 C4 C5 117.11(11) . . ?
F5 C5 C4 117.60(11) . . ?
F5 C5 C6 119.88(11) . . ?
C6 C5 C4 122.52(12) . . ?
C5 C6 H6 119.3(11) . . ?
C5 C6 C7 118.48(12) . . ?
C7 C6 H6 122.2(11) . . ?
C6 C7 H7 119.3(10) . . ?
C6 C7 C8 120.94(12) . . ?
C8 C7 H7 119.7(10) . . ?
C7 C8 H8 122.8(11) . . ?
C9 C8 C7 118.57(12) . . ?
C9 C8 H8 118.6(11) . . ?
C8 C9 C4 122.34(12) . . ?
F9 C9 C4 118.04(11) . . ?
F9 C9 C8 119.62(12) . . ?
C11 C10 N2 121.12(11) . . ?
C11 C10 C15 117.19(11) . . ?
C15 C10 N2 121.67(11) . . ?
F11 C11 C10 117.52(11) . . ?
F11 C11 C12 119.72(11) . . ?
C12 C11 C10 122.76(12) . . ?
C11 C12 H12 118.3(11) . . ?
C11 C12 C13 118.11(12) . . ?
C13 C12 H12 123.5(11) . . ?
C12 C13 H13 119.3(10) . . ?
C12 C13 C14 120.98(12) . . ?
C14 C13 H13 119.7(10) . . ?
C13 C14 H14 122.1(11) . . ?
C15 C14 C13 118.62(12) . . ?
C15 C14 H14 119.3(11) . . ?
C14 C15 C10 122.23(12) . . ?
F15 C15 C10 118.15(11) . . ?
F15 C15 C14 119.61(11) . . ?
Ni1 C16 H16 121.7(11) . . ?
C17 C16 Ni1 75.55(8) . . ?
C17 C16 H16 126.6(11) . . ?
C20 C16 Ni1 73.84(7) . . ?
C20 C16 H16 124.5(11) . . ?
C20 C16 C17 108.57(11) . . ?
Ni1 C17 H17 125.4(10) . . ?
C16 C17 Ni1 64.74(7) . . ?
C16 C17 H17 126.1(10) . . ?
C18 C17 Ni1 72.64(7) . . ?
C18 C17 C16 107.17(11) . . ?
C18 C17 H17 126.7(10) . . ?
Ni1 C18 H18 126.2(10) . . ?
C17 C18 Ni1 70.46(7) . . ?
C17 C18 H18 127.8(11) . . ?
C17 C18 C19 108.58(11) . . ?
C19 C18 Ni1 69.42(7) . . ?
C19 C18 H18 123.6(11) . . ?
Ni1 C19 H19 124.0(10) . . ?
C18 C19 Ni1 71.95(7) . . ?
C18 C19 H19 124.4(10) . . ?
C20 C19 Ni1 69.76(7) . . ?
C20 C19 C18 108.38(11) . . ?
C20 C19 H19 127.2(10) . . ?
Ni1 C20 H20 123.6(10) . . ?
C16 C20 Ni1 66.03(7) . . ?
C16 C20 H20 125.1(10) . . ?
C19 C20 Ni1 72.38(7) . . ?
C19 C20 C16 106.83(11) . . ?
C19 C20 H20 128.0(10) . . ?

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 C1 N2 C2 -177.91(9) . . . . ?
Ni1 C1 N2 C10 4.84(17) . . . . ?
Ni1 C16 C17 C18 60.58(9) . . . . ?
Ni1 C16 C20 C19 -61.27(9) . . . . ?
Ni1 C17 C18 C19 59.14(8) . . . . ?
Ni1 C18 C19 C20 60.55(9) . . . . ?
Ni1 C19 C20 C16 57.22(8) . . . . ?
Cl1 Ni1 C1 N1 -89.84(11) . . . . ?
Cl1 Ni1 C1 N2 87.17(11) . . . . ?
N1 C1 N2 C2 -0.35(13) . . . . ?
N1 C1 N2 C10 -177.60(10) . . . . ?
N1 C4 C5 F5 -0.16(17) . . . . ?
N1 C4 C5 C6 178.92(11) . . . . ?
N1 C4 C9 C8 -178.93(12) . . . . ?
N1 C4 C9 F9 0.93(18) . . . . ?
C1 N1 C3 C2 -0.54(15) . . . . ?
C1 N1 C4 C5 -86.34(15) . . . . ?
C1 N1 C4 C9 94.29(15) . . . . ?
C1 N2 C2 C3 0.03(14) . . . . ?
C1 N2 C10 C11 77.13(16) . . . . ?
C1 N2 C10 C15 -104.21(14) . . . . ?
N2 C2 C3 N1 0.29(14) . . . . ?
N2 C10 C11 F11 2.40(17) . . . . ?
N2 C10 C11 C12 -177.45(12) . . . . ?
N2 C10 C15 C14 178.87(12) . . . . ?
N2 C10 C15 F15 -2.21(18) . . . . ?
C2 N2 C10 C11 -99.77(15) . . . . ?
C2 N2 C10 C15 78.89(16) . . . . ?
C3 N1 C1 Ni1 178.15(9) . . . . ?
C3 N1 C1 N2 0.54(13) . . . . ?
C3 N1 C4 C5 89.61(15) . . . . ?
C3 N1 C4 C9 -89.76(16) . . . . ?
C4 N1 C1 Ni1 -5.46(17) . . . . ?
C4 N1 C1 N2 176.94(10) . . . . ?
C4 N1 C3 C2 -176.93(11) . . . . ?
C4 C5 C6 C7 0.13(19) . . . . ?
C5 C4 C9 C8 1.67(19) . . . . ?
C5 C4 C9 F9 -178.47(11) . . . . ?
C5 C6 C7 C8 1.5(2) . . . . ?
F5 C5 C6 C7 179.19(11) . . . . ?
C6 C7 C8 C9 -1.5(2) . . . . ?
C7 C8 C9 C4 -0.1(2) . . . . ?
C7 C8 C9 F9 -179.99(12) . . . . ?
C9 C4 C5 F5 179.25(11) . . . . ?
C9 C4 C5 C6 -1.67(19) . . . . ?
C10 N2 C2 C3 177.25(11) . . . . ?
C10 C11 C12 C13 -2.2(2) . . . . ?
C11 C10 C15 C14 -2.42(19) . . . . ?
C11 C10 C15 F15 176.50(11) . . . . ?
C11 C12 C13 C14 -0.9(2) . . . . ?
F11 C11 C12 C13 177.92(12) . . . . ?
C12 C13 C14 C15 2.2(2) . . . . ?
C13 C14 C15 C10 -0.5(2) . . . . ?
C13 C14 C15 F15 -179.41(12) . . . . ?
C15 C10 C11 F11 -176.31(11) . . . . ?
C15 C10 C11 C12 3.84(19) . . . . ?
C16 Ni1 C1 N1 87.68(11) . . . . ?
C16 Ni1 C1 N2 -95.31(11) . . . . ?
C16 C17 C18 Ni1 -55.62(8) . . . . ?
C16 C17 C18 C19 3.52(14) . . . . ?
C17 Ni1 C1 N1 124.47(11) . . . . ?
C17 Ni1 C1 N2 -58.52(12) . . . . ?
C17 C16 C20 Ni1 68.19(9) . . . . ?
C17 C16 C20 C19 6.92(14) . . . . ?
C17 C18 C19 Ni1 -59.79(9) . . . . ?
C17 C18 C19 C20 0.76(14) . . . . ?
C18 Ni1 C1 N1 134.42(11) . . . . ?
C18 Ni1 C1 N2 -48.57(17) . . . . ?
C18 C19 C20 Ni1 -61.93(8) . . . . ?
C18 C19 C20 C16 -4.72(14) . . . . ?
C19 Ni1 C1 N1 42.19(18) . . . . ?
C19 Ni1 C1 N2 -140.80(11) . . . . ?
C20 Ni1 C1 N1 50.71(12) . . . . ?
C20 Ni1 C1 N2 -132.28(11) . . . . ?
C20 C16 C17 Ni1 -67.06(9) . . . . ?
C20 C16 C17 C18 -6.48(14) . . . . ?

_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 1.156
_oxdiff_exptl_absorpt_empirical_full_min 0.943
####################################################################### 
# 
# 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_4d
_database_code_depnum_ccdc_archive 'CCDC 2338061'
loop_
_audit_author_name
_audit_author_address
'Mikhail Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2024-03-06 deposited with the CCDC.	2024-07-16 downloaded from the CCDC.
;
_audit_creation_date             2023-10-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H13 Cl F4 N2 Ni'
_chemical_formula_sum            'C20 H13 Cl F4 N2 Ni'
_chemical_formula_weight         451.48
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H13N2F4ClNi
_chemical_oxdiff_usercomment     TAR-70
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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/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                   10.87858(6)
_cell_length_b                   10.65567(5)
_cell_length_c                   15.41970(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.6788(5)
_cell_angle_gamma                90
_cell_volume                     1785.476(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    19140
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.9420
_cell_measurement_theta_min      2.8580
_shelx_estimated_absorpt_T_max   0.509
_shelx_estimated_absorpt_T_min   0.252
_exptl_absorpt_coefficient_mu    3.393
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.328
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.91a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.680
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             912
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.3943
-5 1 -5 0.1245
-1 0 -1 0.1198
1 0 1 0.1360
5 -2 5 0.1409
-5 1 0 0.1078
-2 -1 -2 0.1837
0 0 1 0.1462
0 1 0 0.1622
-1 0 0 0.1055
1 0 0 0.1200
2 -2 5 0.1426
0 0 -1 0.1227

_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.23
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0004 -1.0000 0.0024 0.0422 -0.0593 -0.1249
-5.0014 0.9943 -4.9998 -0.3116 0.7830 -0.3103
-0.9983 -0.0005 -1.0008 -0.0536 0.1447 -0.0869
0.9983 0.0005 1.0008 0.0536 -0.1447 0.0869
5.0004 -2.0000 5.0044 0.3539 -0.8428 0.1847
-4.9988 1.0036 0.0011 -0.5825 0.3753 -0.2074
-2.0002 -0.9993 -1.9969 -0.0657 0.2303 -0.2986
0.0000 -0.0006 1.0000 -0.0541 -0.0816 0.0202
0.0006 1.0000 -0.0009 -0.0422 0.0592 0.1250
-0.9999 0.0009 -0.0004 -0.1080 0.0633 -0.0665
0.9995 -0.0013 0.0012 0.1080 -0.0634 0.0664
1.9998 -2.0016 5.0034 0.0298 -0.6531 -0.0153
-0.0003 0.0005 -0.9999 0.0541 0.0816 -0.0203

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24172
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.226
_diffrn_reflns_theta_min         4.068
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -45.00  39.00   0.50    0.21    --  -41.38  40.00  22.00  168
  2  ω    -71.00 -24.00   0.50    0.21    -- -100.00  61.00 -30.00   94
  3  ω    -51.00 -21.00   0.50    0.21    -- -100.00  45.00-120.00   60
  4  ω    -45.00 -19.00   0.50    0.21    -- -100.00  40.00  22.00   52
  5  ω    -71.00 -24.00   0.50    0.21    -- -100.00  61.00-120.00   94
  6  ω    -51.00 -21.00   0.50    0.21    -- -100.00  45.00-150.00   60
  7  ω     34.00  99.00   0.50    0.21    --   41.38-125.00-180.00  130
  8  ω     45.00 108.00   0.50    0.21    --  121.50-111.00-180.00  126
  9  ω     45.00 108.00   0.50    0.21    --  121.50-111.00-150.00  126
 10  ω     45.00 108.00   0.50    0.21    --  121.50-111.00 -90.00  126
 11  ω     45.00 108.00   0.50    0.21    --  121.50-111.00 -30.00  126
 12  ω     79.00 104.00   0.50    0.21    --  121.50 -95.00 -90.00   50
 13  ω     41.00 106.00   0.50    0.21    --  121.50 -95.00 -30.00  130
 14  ω     43.00 160.00   0.50    0.21    --  121.50 -86.00 120.91  234
 15  ω     45.00 108.00   0.50    0.21    --  121.50-111.00  90.00  126
 16  ω     41.00 106.00   0.50    0.21    --  121.50 -94.00  67.58  130
 17  ω     45.00 108.00   0.50    0.21    --  121.50-111.00  30.00  126
 18  ω     34.00  99.00   0.50    0.21    --   41.38-125.00  60.00  130
 19  ω    -39.00  45.00   0.50    0.21    --   41.38 -40.00-131.00  168
 20  ω     47.00 105.00   0.50    0.21    --  121.50 -77.00-180.00  116
 21  ω     47.00 105.00   0.50    0.21    --  121.50 -77.00 -90.00  116
 22  ω     47.00 105.00   0.50    0.21    --  121.50 -77.00   0.00  116
 23  ω     47.00 105.00   0.50    0.21    --  121.50 -77.00  60.00  116
 24  ω     47.00 105.00   0.50    0.21    --  121.50 -77.00 120.00  116
 25  ω     47.00 105.00   0.50    0.21    --  121.50 -77.00 150.00  116
 26  ω      1.00  42.00   0.50    0.21    --   41.38  91.00 127.66   82
 27  ω    103.00 178.00   0.50    0.21    --  121.50 111.00 150.00  150
 28  ω     71.00  97.00   0.50    0.21    --  121.50 178.00 150.00   52
 29  ω    103.00 178.00   0.50    0.21    --  121.50 111.00  60.00  150
 30  ω    116.00 142.00   0.50    0.21    --  121.50 111.00 -30.00   52
 31  ω    105.00 130.00   0.50    0.21    --  121.50 178.00-150.00   50
 32  ω    103.00 178.00   0.50    0.21    --  121.50 111.00-120.00  150
 33  ω     42.00 178.00   0.50    0.21    --  121.50  15.00-150.00  272
 34  ω     93.00 147.00   0.50    0.21    --  121.50  45.00-180.00  108
 35  ω     92.00 178.00   0.50    0.21    --  121.50  61.00-120.00  172
 36  ω     91.00 178.00   0.50    0.21    --  121.50  40.00  22.00  174
 37  ω     87.00 178.00   0.50    0.21    --  121.50  77.00  30.00  182
 38  ω     87.00 178.00   0.50    0.21    --  121.50  77.00  60.00  182
 39  ω     87.00 178.00   0.50    0.21    --  121.50  77.00 120.00  182
 40  ω    112.00 155.00   0.50    0.21    --  121.50  30.00   0.00   86
 41  ω     11.00 122.00   0.50    0.21    --   41.38  40.00  22.00  222
 42  ω   -122.00 -11.00   0.50    0.21    --  -41.38 -40.00-131.00  222
 43  ω   -177.00 -69.00   0.50    0.21    -- -100.00 -40.00-131.00  216
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1080245000
_diffrn_orient_matrix_UB_12      -0.0423228000
_diffrn_orient_matrix_UB_13      -0.0541449000
_diffrn_orient_matrix_UB_21      -0.0632181000
_diffrn_orient_matrix_UB_22      0.0591664000
_diffrn_orient_matrix_UB_23      -0.0815929000
_diffrn_orient_matrix_UB_31      0.0665744000
_diffrn_orient_matrix_UB_32      0.1249584000
_diffrn_orient_matrix_UB_33      0.0203171000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3876
_reflns_number_total             3896
_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 1.171.43.91a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 42.102a 64-bit (release 15-09-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.91a (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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.00057(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         3896
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0277
_refine_ls_restrained_S_all      1.105
_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)+(0.0259P)²+1.4482P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0676
_refine_ls_wR_factor_ref         0.0677
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C6-F6 \\sim C8-F8A \\sim C12-F12 \\sim C14-F14A
 with sigma of 0.02
 C7-F8A \\sim C9-F8A
 with sigma of 0.02
3. Restrained planarity
 C4, C5, C6, F6, C7, F7, C8, F8A, C9
 with sigma of 0.1
 C10, C11, C12, F12, C13, F13, C14, F14A, C15
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(F6) = Uanis(F8A)
Uanis(F12) = Uanis(F14A)
5. Others
 Sof(H6A)=Sof(F8A)=1-FVAR(1)
 Sof(F6)=Sof(H8)=FVAR(1)
 Sof(H12A)=Sof(F14A)=1-FVAR(2)
 Sof(F12)=Sof(H14)=FVAR(2)
6.a Aromatic/amide H refined with riding coordinates:
 C6(H6A), C8(H8), C12(H12A), C14(H14)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.29032(2) 0.67715(2) 0.62243(2) 0.01588(8) Uani 1 1 d . . . . .
Cl1 Cl 0.27721(3) 0.88225(3) 0.60035(2) 0.02018(9) Uani 1 1 d . . . . .
N1 N 0.30717(11) 0.65951(12) 0.81219(8) 0.0176(3) Uani 1 1 d . . . . .
C1 C 0.36347(14) 0.67334(14) 0.73548(9) 0.0176(3) Uani 1 1 d . . . . .
N2 N 0.48540(12) 0.66235(13) 0.75856(8) 0.0186(3) Uani 1 1 d . . . . .
C2 C 0.50426(15) 0.63987(16) 0.84741(10) 0.0211(3) Uani 1 1 d . . . . .
H2 H 0.5808(19) 0.630(2) 0.8750(13) 0.025 Uiso 1 1 d . U . . .
C3 C 0.39255(14) 0.63790(15) 0.88103(10) 0.0201(3) Uani 1 1 d . . . . .
H3 H 0.3695(18) 0.6277(19) 0.9389(13) 0.024 Uiso 1 1 d . U . . .
C4 C 0.17720(13) 0.66825(14) 0.82283(9) 0.0171(3) Uani 1 1 d . . . . .
C5 C 0.10992(14) 0.76097(14) 0.77833(9) 0.0180(3) Uani 1 1 d . . . . .
H5 H 0.1460(19) 0.8135(19) 0.7407(13) 0.022 Uiso 1 1 d . U . . .
C6 C -0.01401(14) 0.77056(14) 0.79265(9) 0.0184(3) Uani 1 1 d D . . . .
H6A H -0.061874 0.832811 0.762647 0.022 Uiso 0.020(2) 1 calc R U P A 2
F6 F -0.08190(9) 0.85897(10) 0.75077(6) 0.0249(2) Uani 0.980(2) 1 d D . P A 1
C7 C -0.06985(13) 0.69105(15) 0.84997(9) 0.0184(3) Uani 1 1 d D . . . .
F7 F -0.19064(8) 0.70594(9) 0.86330(6) 0.02251(19) Uani 1 1 d . . . . .
C8 C -0.00358(14) 0.59806(15) 0.89272(10) 0.0205(3) Uani 1 1 d D . . . .
H8 H -0.042712 0.542493 0.930933 0.025 Uiso 0.980(2) 1 calc R U P A 1
F8A F -0.0529(19) 0.534(3) 0.9529(18) 0.0249(2) Uani 0.020(2) 1 d D . P A 2
C9 C 0.12171(14) 0.58634(15) 0.87926(10) 0.0199(3) Uani 1 1 d D . . . .
H9 H 0.1680(18) 0.524(2) 0.9067(13) 0.024 Uiso 1 1 d . U . . .
C10 C 0.58436(14) 0.67279(15) 0.70063(9) 0.0191(3) Uani 1 1 d . . . . .
C11 C 0.58325(14) 0.76861(16) 0.63933(10) 0.0208(3) Uani 1 1 d . . . . .
H11 H 0.5201(19) 0.826(2) 0.6336(13) 0.025 Uiso 1 1 d . U . . .
C12 C 0.68290(15) 0.77903(16) 0.58711(10) 0.0221(3) Uani 1 1 d D . . . .
H12A H 0.683111 0.842554 0.543888 0.027 Uiso 0.3697(19) 1 calc R U P B 2
F12 F 0.68672(14) 0.86499(14) 0.52846(9) 0.0240(3) Uani 0.6303(19) 1 d D . P B
1
C13 C 0.78186(14) 0.69851(17) 0.59692(10) 0.0227(3) Uani 1 1 d . . . . .
F13 F 0.87967(9) 0.71403(10) 0.54760(6) 0.0288(2) Uani 1 1 d . . . . .
C14 C 0.78144(14) 0.60379(16) 0.65736(10) 0.0223(3) Uani 1 1 d D . . . .
H14 H 0.849627 0.548288 0.663516 0.027 Uiso 0.6303(19) 1 calc R U P B 1
F14A F 0.8762(2) 0.5372(2) 0.66460(16) 0.0240(3) Uani 0.3697(19) 1 d D . P B 2
C15 C 0.68162(14) 0.58882(16) 0.70956(10) 0.0204(3) Uani 1 1 d . . . . .
H15 H 0.6812(18) 0.525(2) 0.7512(13) 0.024 Uiso 1 1 d . U . . .
C16 C 0.26322(15) 0.48756(15) 0.61892(10) 0.0222(3) Uani 1 1 d . . . . .
H16 H 0.2745(18) 0.437(2) 0.6683(14) 0.027 Uiso 1 1 d . U . . .
C17 C 0.15134(15) 0.54119(16) 0.58590(11) 0.0250(3) Uani 1 1 d . . . . .
H17 H 0.077(2) 0.536(2) 0.6121(14) 0.030 Uiso 1 1 d . U . . .
C18 C 0.17963(17) 0.61256(17) 0.51342(11) 0.0265(3) Uani 1 1 d . . . . .
H18 H 0.125(2) 0.667(2) 0.4825(15) 0.032 Uiso 1 1 d . U . . .
C19 C 0.30747(17) 0.59172(16) 0.49503(10) 0.0253(3) Uani 1 1 d . . . . .
H19 H 0.351(2) 0.626(2) 0.4484(14) 0.030 Uiso 1 1 d . U . . .
C20 C 0.35858(15) 0.51376(15) 0.55876(11) 0.0230(3) Uani 1 1 d . . . . .
H20 H 0.4416(19) 0.486(2) 0.5662(13) 0.028 Uiso 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 Cl1 2.2154(4) . ?
Ni1 C1 1.8826(15) . ?
Ni1 C16 2.0419(16) . ?
Ni1 C17 2.1499(16) . ?
Ni1 C18 2.1354(16) . ?
Ni1 C19 2.1811(15) . ?
Ni1 C20 2.1481(16) . ?
N1 C1 1.3651(18) . ?
N1 C3 1.3966(19) . ?
N1 C4 1.4340(18) . ?
C1 N2 1.3622(19) . ?
N2 C2 1.3964(19) . ?
N2 C10 1.4350(18) . ?
C2 H2 0.92(2) . ?
C2 C3 1.343(2) . ?
C3 H3 0.94(2) . ?
C4 C5 1.391(2) . ?
C4 C9 1.390(2) . ?
C5 H5 0.91(2) . ?
C5 C6 1.380(2) . ?
C6 H6A 0.9500 . ?
C6 F6 1.3435(18) . ?
C6 C7 1.385(2) . ?
C7 F7 1.3489(17) . ?
C7 C8 1.375(2) . ?
C8 H8 0.9500 . ?
C8 F8A 1.286(16) . ?
C8 C9 1.394(2) . ?
C9 H9 0.92(2) . ?
C10 C11 1.391(2) . ?
C10 C15 1.388(2) . ?
C11 H11 0.92(2) . ?
C11 C12 1.385(2) . ?
C12 H12A 0.9500 . ?
C12 F12 1.289(2) . ?
C12 C13 1.379(2) . ?
C13 F13 1.3467(17) . ?
C13 C14 1.374(2) . ?
C14 H14 0.9500 . ?
C14 F14A 1.253(3) . ?
C14 C15 1.391(2) . ?
C15 H15 0.93(2) . ?
C16 H16 0.93(2) . ?
C16 C17 1.417(2) . ?
C16 C20 1.451(2) . ?
C17 H17 0.92(2) . ?
C17 C18 1.398(2) . ?
C18 H18 0.95(2) . ?
C18 C19 1.449(3) . ?
C19 H19 0.95(2) . ?
C19 C20 1.383(2) . ?
C20 H20 0.95(2) . ?

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
C1 Ni1 Cl1 100.66(5) . . ?
C1 Ni1 C16 93.29(7) . . ?
C1 Ni1 C17 119.32(7) . . ?
C1 Ni1 C18 156.98(7) . . ?
C1 Ni1 C19 140.79(7) . . ?
C1 Ni1 C20 105.40(7) . . ?
C16 Ni1 Cl1 164.52(5) . . ?
C16 Ni1 C17 39.42(7) . . ?
C16 Ni1 C18 65.47(7) . . ?
C16 Ni1 C19 65.26(6) . . ?
C16 Ni1 C20 40.42(6) . . ?
C17 Ni1 Cl1 125.81(5) . . ?
C17 Ni1 C19 64.63(6) . . ?
C18 Ni1 Cl1 99.62(5) . . ?
C18 Ni1 C17 38.08(7) . . ?
C18 Ni1 C19 39.22(7) . . ?
C18 Ni1 C20 64.74(7) . . ?
C19 Ni1 Cl1 106.31(5) . . ?
C20 Ni1 Cl1 138.63(5) . . ?
C20 Ni1 C17 65.67(6) . . ?
C20 Ni1 C19 37.26(6) . . ?
C1 N1 C3 111.53(12) . . ?
C1 N1 C4 125.23(12) . . ?
C3 N1 C4 123.23(12) . . ?
N1 C1 Ni1 128.12(11) . . ?
N2 C1 Ni1 127.45(11) . . ?
N2 C1 N1 103.60(12) . . ?
C1 N2 C2 111.57(12) . . ?
C1 N2 C10 125.48(13) . . ?
C2 N2 C10 122.95(13) . . ?
N2 C2 H2 124.0(13) . . ?
C3 C2 N2 106.69(13) . . ?
C3 C2 H2 129.3(13) . . ?
N1 C3 H3 122.7(12) . . ?
C2 C3 N1 106.59(13) . . ?
C2 C3 H3 130.7(12) . . ?
C5 C4 N1 119.23(13) . . ?
C9 C4 N1 119.35(13) . . ?
C9 C4 C5 121.39(14) . . ?
C4 C5 H5 121.3(13) . . ?
C6 C5 C4 117.97(14) . . ?
C6 C5 H5 120.7(13) . . ?
C5 C6 H6A 119.4 . . ?
C5 C6 C7 121.17(14) . . ?
F6 C6 C5 119.62(14) . . ?
F6 C6 C7 119.21(13) . . ?
C7 C6 H6A 119.4 . . ?
F7 C7 C6 118.99(14) . . ?
F7 C7 C8 120.29(14) . . ?
C8 C7 C6 120.72(14) . . ?
C7 C8 H8 120.4 . . ?
C7 C8 C9 119.18(14) . . ?
F8A C8 C7 119.9(8) . . ?
F8A C8 C9 120.3(8) . . ?
C9 C8 H8 120.4 . . ?
C4 C9 C8 119.55(14) . . ?
C4 C9 H9 119.7(13) . . ?
C8 C9 H9 120.8(13) . . ?
C11 C10 N2 119.80(14) . . ?
C15 C10 N2 118.62(14) . . ?
C15 C10 C11 121.54(14) . . ?
C10 C11 H11 122.4(13) . . ?
C12 C11 C10 118.15(15) . . ?
C12 C11 H11 119.4(13) . . ?
C11 C12 H12A 119.5 . . ?
F12 C12 C11 121.11(16) . . ?
F12 C12 C13 117.92(15) . . ?
C13 C12 C11 120.96(15) . . ?
C13 C12 H12A 119.5 . . ?
F13 C13 C12 119.66(15) . . ?
F13 C13 C14 120.06(15) . . ?
C14 C13 C12 120.27(14) . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.28(15) . . ?
F14A C14 C13 116.61(17) . . ?
F14A C14 C15 123.05(19) . . ?
C15 C14 H14 119.9 . . ?
C10 C15 C14 118.75(15) . . ?
C10 C15 H15 120.6(12) . . ?
C14 C15 H15 120.7(12) . . ?
Ni1 C16 H16 122.1(13) . . ?
C17 C16 Ni1 74.40(10) . . ?
C17 C16 H16 127.0(12) . . ?
C17 C16 C20 108.68(14) . . ?
C20 C16 Ni1 73.73(9) . . ?
C20 C16 H16 124.1(12) . . ?
Ni1 C17 H17 123.0(14) . . ?
C16 C17 Ni1 66.18(9) . . ?
C16 C17 H17 125.2(14) . . ?
C18 C17 Ni1 70.40(9) . . ?
C18 C17 C16 106.81(15) . . ?
C18 C17 H17 127.6(14) . . ?
Ni1 C18 H18 121.1(14) . . ?
C17 C18 Ni1 71.52(9) . . ?
C17 C18 H18 125.5(14) . . ?
C17 C18 C19 108.80(15) . . ?
C19 C18 Ni1 72.09(9) . . ?
C19 C18 H18 125.7(14) . . ?
Ni1 C19 H19 125.9(13) . . ?
C18 C19 Ni1 68.69(9) . . ?
C18 C19 H19 126.9(13) . . ?
C20 C19 Ni1 70.08(9) . . ?
C20 C19 C18 108.09(15) . . ?
C20 C19 H19 125.0(13) . . ?
Ni1 C20 H20 123.0(13) . . ?
C16 C20 Ni1 65.85(9) . . ?
C16 C20 H20 124.4(13) . . ?
C19 C20 Ni1 72.66(9) . . ?
C19 C20 C16 107.10(15) . . ?
C19 C20 H20 128.3(13) . . ?

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 C1 N2 C2 -169.09(12) . . . . ?
Ni1 C1 N2 C10 11.3(2) . . . . ?
Ni1 C16 C17 C18 58.91(12) . . . . ?
Ni1 C16 C20 C19 -61.34(11) . . . . ?
Ni1 C17 C18 C19 62.86(11) . . . . ?
Ni1 C18 C19 C20 59.19(12) . . . . ?
Ni1 C19 C20 C16 57.01(11) . . . . ?
Cl1 Ni1 C1 N1 97.22(14) . . . . ?
Cl1 Ni1 C1 N2 -94.95(14) . . . . ?
N1 C1 N2 C2 1.08(17) . . . . ?
N1 C1 N2 C10 -178.57(14) . . . . ?
N1 C4 C5 C6 -177.30(13) . . . . ?
N1 C4 C9 C8 177.20(14) . . . . ?
C1 N1 C3 C2 0.84(19) . . . . ?
C1 N1 C4 C5 -40.9(2) . . . . ?
C1 N1 C4 C9 140.95(15) . . . . ?
C1 N2 C2 C3 -0.61(19) . . . . ?
C1 N2 C10 C11 44.2(2) . . . . ?
C1 N2 C10 C15 -138.09(16) . . . . ?
N2 C2 C3 N1 -0.14(18) . . . . ?
N2 C10 C11 C12 177.22(14) . . . . ?
N2 C10 C15 C14 -175.81(14) . . . . ?
C2 N2 C10 C11 -135.39(16) . . . . ?
C2 N2 C10 C15 42.3(2) . . . . ?
C3 N1 C1 Ni1 168.91(12) . . . . ?
C3 N1 C1 N2 -1.17(17) . . . . ?
C3 N1 C4 C5 137.74(15) . . . . ?
C3 N1 C4 C9 -40.4(2) . . . . ?
C4 N1 C1 Ni1 -12.3(2) . . . . ?
C4 N1 C1 N2 177.61(13) . . . . ?
C4 N1 C3 C2 -177.96(14) . . . . ?
C4 C5 C6 F6 -179.97(13) . . . . ?
C4 C5 C6 C7 0.4(2) . . . . ?
C5 C4 C9 C8 -0.9(2) . . . . ?
C5 C6 C7 F7 178.50(13) . . . . ?
C5 C6 C7 C8 -1.6(2) . . . . ?
C6 C7 C8 F8A 172(2) . . . . ?
C6 C7 C8 C9 1.5(2) . . . . ?
F6 C6 C7 F7 -1.1(2) . . . . ?
F6 C6 C7 C8 178.80(14) . . . . ?
C7 C8 C9 C4 -0.2(2) . . . . ?
F7 C7 C8 F8A -8(2) . . . . ?
F7 C7 C8 C9 -178.62(13) . . . . ?
F8A C8 C9 C4 -171(2) . . . . ?
C9 C4 C5 C6 0.8(2) . . . . ?
C10 N2 C2 C3 179.05(14) . . . . ?
C10 C11 C12 F12 179.24(15) . . . . ?
C10 C11 C12 C13 -1.5(2) . . . . ?
C11 C10 C15 C14 1.8(2) . . . . ?
C11 C12 C13 F13 -177.33(14) . . . . ?
C11 C12 C13 C14 1.9(2) . . . . ?
C12 C13 C14 F14A -177.61(19) . . . . ?
C12 C13 C14 C15 -0.4(2) . . . . ?
F12 C12 C13 F13 2.0(2) . . . . ?
F12 C12 C13 C14 -178.78(16) . . . . ?
C13 C14 C15 C10 -1.4(2) . . . . ?
F13 C13 C14 F14A 1.7(3) . . . . ?
F13 C13 C14 C15 178.81(14) . . . . ?
F14A C14 C15 C10 175.6(2) . . . . ?
C15 C10 C11 C12 -0.4(2) . . . . ?
C16 Ni1 C1 N1 -76.05(14) . . . . ?
C16 Ni1 C1 N2 91.78(14) . . . . ?
C16 C17 C18 Ni1 -56.26(11) . . . . ?
C16 C17 C18 C19 6.60(19) . . . . ?
C17 Ni1 C1 N1 -44.82(16) . . . . ?
C17 Ni1 C1 N2 123.00(14) . . . . ?
C17 C16 C20 Ni1 66.77(11) . . . . ?
C17 C16 C20 C19 5.44(18) . . . . ?
C17 C18 C19 Ni1 -62.50(12) . . . . ?
C17 C18 C19 C20 -3.31(19) . . . . ?
C18 Ni1 C1 N1 -54.1(2) . . . . ?
C18 Ni1 C1 N2 113.68(19) . . . . ?
C18 C19 C20 Ni1 -58.33(11) . . . . ?
C18 C19 C20 C16 -1.32(18) . . . . ?
C19 Ni1 C1 N1 -129.72(14) . . . . ?
C19 Ni1 C1 N2 38.10(19) . . . . ?
C20 Ni1 C1 N1 -115.23(14) . . . . ?
C20 Ni1 C1 N2 52.59(15) . . . . ?
C20 C16 C17 Ni1 -66.33(11) . . . . ?
C20 C16 C17 C18 -7.43(18) . . . . ?

_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 1.160
_oxdiff_exptl_absorpt_empirical_full_min 0.849
####################################################################### 
# 
# 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_4g
_database_code_depnum_ccdc_archive 'CCDC 2338063'
loop_
_audit_author_name
_audit_author_address
'Mikhail Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2024-03-06 deposited with the CCDC.	2024-07-16 downloaded from the CCDC.
;
_audit_creation_date             2024-01-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H11 Cl F6 N2 Ni'
_chemical_formula_sum            'C20 H11 Cl F6 N2 Ni'
_chemical_formula_weight         487.47
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H11 Cl F6 N2 Ni'
_chemical_oxdiff_usercomment     TAR-86_red_block
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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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'
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                   10.34845(5)
_cell_length_b                   17.63964(7)
_cell_length_c                   10.81434(6)
_cell_angle_alpha                90
_cell_angle_beta                 108.9317(5)
_cell_angle_gamma                90
_cell_volume                     1867.293(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    27158
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      80.1450
_cell_measurement_theta_min      4.9690
_shelx_estimated_absorpt_T_max   0.555
_shelx_estimated_absorpt_T_min   0.461
_exptl_absorpt_coefficient_mu    3.457
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.253
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.104a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear intense red'
_exptl_crystal_density_diffrn    1.734
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             976
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 10 3 0.1071
2 -3 -5 0.1547
3 -4 4 0.1309
0 11 -2 0.1166
-5 -4 -3 0.1179
-2 -10 3 0.1349
2 -1 1 0.1284
2 -11 -1 0.1613
-1 -2 0 0.1217
0 -5 2 0.1368
5 3 -2 0.1235
-1 0 -1 0.1066
-2 -5 -3 0.1337
-1 0 1 0.0749
-1 -2 2 0.1030
1 0 0 0.1268
4 -7 1 0.1438
-4 5 -3 0.0775
2 5 2 0.0937
1 2 0 0.1085
-2 2 7 0.0633
-1 5 6 0.0660
0 3 6 0.0688
-4 0 5 0.0680
-4 -8 -1 0.1193
1 0 -1 0.1183
1 -1 -1 0.1277
-1 2 -1 0.0714

_exptl_crystal_size_max          0.265
_exptl_crystal_size_mid          0.216
_exptl_crystal_size_min          0.193
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2.9956 9.9892 2.9981 0.3287 0.2757 0.9301
1.9960 -2.9978 -5.0035 -0.2470 0.3696 -0.6194
2.9940 -3.9921 4.0072 0.4557 -0.7968 -0.2232
-0.0036 10.9993 -1.9946 0.4055 0.8208 0.4182
-5.0021 -3.9845 -2.9998 -1.0318 0.3253 0.0725
-1.9954 -10.0041 2.9968 -0.5365 -0.8173 -0.1329
1.9965 -1.0030 1.0049 0.2700 -0.2440 -0.1667
2.0067 -10.9968 -1.0002 -0.3633 -0.5331 -0.7732
-1.0015 -1.9991 0.0018 -0.2242 -0.0705 -0.0084
0.0017 -5.0027 1.9975 -0.1085 -0.5038 -0.1257
4.9977 2.9957 -2.0034 0.6341 0.2213 -0.4164
-0.9983 0.0012 -1.0026 -0.1946 0.1554 0.0294
-1.9977 -4.9902 -3.0087 -0.7064 0.1668 -0.2438
-0.9999 -0.0024 1.0001 -0.0556 -0.0844 0.1479
-0.9974 -2.0015 2.0004 -0.0847 -0.3100 0.1094
0.9996 -0.0017 0.0007 0.1250 -0.0356 -0.0888
3.9964 -7.0089 0.9927 0.2218 -0.6311 -0.6376
-3.9907 5.0030 -3.0025 -0.4603 0.7653 0.4204
2.0034 4.9961 1.9972 0.6370 -0.0456 0.1837
1.0004 1.9977 -0.0001 0.2241 0.0703 0.0085
-1.9959 2.0029 7.0016 0.3368 -0.6614 0.6892
-1.0002 5.0055 5.9994 0.5403 -0.4178 0.6877
0.0038 2.9939 6.0028 0.5665 -0.5602 0.5008
-3.9986 -0.0113 4.9992 -0.1528 -0.4574 0.6504
-3.9962 -7.9957 -1.0122 -0.9663 -0.1604 -0.0946
1.0007 -0.0006 -0.9987 0.0556 0.0841 -0.1480
0.9994 -0.9998 -1.0012 0.0058 0.0316 -0.1967
-1.0002 2.0025 -0.9986 -0.0954 0.2609 0.1273

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0111
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            33931
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.164
_diffrn_reflns_theta_min         4.998
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -33.00  76.00   0.50    0.10    --   41.38 -76.00 163.00  218
  2  ω     45.00 108.00   0.50    0.40    --  121.50-111.00 150.00  126
  3  ω     45.00 108.00   0.50    0.40    --  121.50-111.00   0.00  126
  4  ω     45.00 108.00   0.50    0.40    --  121.50-111.00 -60.00  126
  5  ω     45.00 108.00   0.50    0.40    --  121.50-111.00-150.00  126
  6  ω    -43.00  27.00   0.50    0.10    --   41.38 -19.00-180.00  140
  7  ω    -43.00  27.00   0.50    0.10    --   41.38 -19.00   0.00  140
  8  ω     45.00 108.00   0.50    0.40    --  121.50-111.00 120.00  126
  9  ω     45.00 108.00   0.50    0.40    --  121.50-111.00  90.00  126
 10  ω     41.00 106.00   0.50    0.40    --  121.50 -95.00  90.00  130
 11  ω     41.00 106.00   0.50    0.40    --  121.50 -95.00 120.00  130
 12  ω     41.00 106.00   0.50    0.40    --  121.50 -95.00 150.00  130
 13  ω     41.00 106.00   0.50    0.40    --  121.50 -95.00  60.00  130
 14  ω     45.00 108.00   0.50    0.40    --  121.50-111.00  30.00  126
 15  ω     41.00 106.00   0.50    0.40    --  121.50 -95.00   0.00  130
 16  ω     45.00 158.00   0.50    0.40    --  121.50 -82.00 -62.88  226
 17  ω     41.00 106.00   0.50    0.40    --  121.50 -95.00-120.00  130
 18  ω     43.00 160.00   0.50    0.40    --  121.50 -86.00  64.10  234
 19  ω     43.00 160.00   0.50    0.40    --  121.50 -86.00  64.10  234
 20  ω     41.00 106.00   0.50    0.40    --  121.50 -95.00 150.00  130
 21  ω     47.00 101.00   0.50    0.40    --  121.50 -76.00 163.00  108
 22  ω     47.00 105.00   0.50    0.40    --  121.50 -77.00 120.00  116
 23  ω     47.00 105.00   0.50    0.40    --  121.50 -77.00  90.00  116
 24  ω     46.00 158.00   0.50    0.40    --  121.50 -80.00 107.97  224
 25  ω     47.00 105.00   0.50    0.40    --  121.50 -77.00   0.00  116
 26  ω     47.00 105.00   0.50    0.40    --  121.50 -77.00-120.00  116
 27  ω     84.00 178.00   0.50    0.40    --  121.50  30.00 -30.00  188
 28  ω     87.00 178.00   0.50    0.40    --  121.50  77.00  30.00  182
 29  ω     92.00 178.00   0.50    0.40    --  121.50  61.00   0.00  172
 30  ω     87.00 178.00   0.50    0.40    --  121.50  77.00 -60.00  182
 31  ω     87.00 178.00   0.50    0.40    --  121.50  76.00 -69.00  182
 32  ω     92.00 178.00   0.50    0.40    --  121.50  61.00 -60.00  172
 33  ω     92.00 178.00   0.50    0.40    --  121.50  61.00-120.00  172
 34  ω     92.00 178.00   0.50    0.40    --  121.50  45.00 -90.00  172
 35  ω     87.00 178.00   0.50    0.40    --  121.50  77.00-150.00  182
 36  ω     14.00 117.00   0.50    0.10    --   41.38  57.00 -60.00  206
 37  ω     14.00  98.00   0.50    0.10    --   41.38  57.00  60.00  168
 38  ω      0.00  41.00   0.50    0.10    --   41.38  92.00  28.49   82
 39  ω     -3.00  23.00   0.50    0.10    --   41.38  99.00 139.45   52
 40  ω    103.00 178.00   0.50    0.40    --  121.50 111.00  90.00  150
 41  ω     63.00 146.00   0.50    0.40    --  121.50 178.00 -30.00  166
 42  ω     63.00 146.00   0.50    0.40    --  121.50 178.00 -60.00  166
 43  ω    103.00 178.00   0.50    0.40    --  121.50 111.00-180.00  150
 44  ω   -117.00  -7.00   0.50    0.10    --  -41.38 -76.00 163.00  220
 45  ω   -175.00 -66.00   0.50    0.40    -- -100.00 -76.00 163.00  218
 46  ω   -101.00 -24.00   0.50    0.40    -- -100.00  76.00 -69.00  154
 47  ω    -82.00 -23.00   0.50    0.40    -- -100.00 111.00   0.00  118
 48  ω    -75.00  34.00   0.50    0.10    --  -41.38  76.00 -69.00  218
 49  ω    -51.00 -21.00   0.50    0.40    -- -100.00  45.00  60.00   60
 50  ω    -51.00 -21.00   0.50    0.40    -- -100.00  45.00 150.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1250852000
_diffrn_orient_matrix_UB_12      0.0495282000
_diffrn_orient_matrix_UB_13      0.0695961000
_diffrn_orient_matrix_UB_21      -0.0354034000
_diffrn_orient_matrix_UB_22      0.0529044000
_diffrn_orient_matrix_UB_23      -0.1196851000
_diffrn_orient_matrix_UB_31      -0.0887941000
_diffrn_orient_matrix_UB_32      0.0487236000
_diffrn_orient_matrix_UB_33      0.0591788000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4059
_reflns_number_total             4083
_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 1.171.43.104a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.104a 64-bit (release 22-12-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.104a (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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.00144(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         4083
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0248
_refine_ls_R_factor_gt           0.0246
_refine_ls_restrained_S_all      1.098
_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)+(0.0263P)²+1.1473P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0622
_refine_ls_wR_factor_ref         0.0623
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.33424(2) 0.32428(2) 0.42402(2) 0.01395(8) Uani 1 1 d . . . . .
Cl1 Cl 0.55853(3) 0.33109(2) 0.47727(3) 0.01790(8) Uani 1 1 d . . . . .
N1 N 0.27124(11) 0.48669(6) 0.40316(10) 0.0152(2) Uani 1 1 d . . . . .
C1 C 0.29191(12) 0.42034(7) 0.34752(12) 0.0146(2) Uani 1 1 d . . . . .
N2 N 0.26825(11) 0.43921(6) 0.22009(10) 0.0147(2) Uani 1 1 d . . . . .
C2 C 0.23304(13) 0.51563(7) 0.19694(13) 0.0171(2) Uani 1 1 d . . . . .
H2 H 0.2169(18) 0.5372(10) 0.1137(18) 0.021 Uiso 1 1 d . U . . .
C3 C 0.23470(13) 0.54540(7) 0.31153(13) 0.0176(2) Uani 1 1 d . . . . .
H3 H 0.2217(18) 0.5947(11) 0.3373(17) 0.021 Uiso 1 1 d . U . . .
C4 C 0.28707(13) 0.49496(7) 0.53871(12) 0.0158(2) Uani 1 1 d . . . . .
C5 C 0.18945(14) 0.53374(8) 0.57627(13) 0.0190(3) Uani 1 1 d . . . . .
F5 F 0.07925(9) 0.56455(5) 0.48740(8) 0.02620(19) Uani 1 1 d . . . . .
C6 C 0.20287(15) 0.54148(8) 0.70752(14) 0.0222(3) Uani 1 1 d . . . . .
F6 F 0.10653(10) 0.57795(6) 0.74272(9) 0.0330(2) Uani 1 1 d . . . . .
C7 C 0.31525(15) 0.51075(8) 0.80086(13) 0.0216(3) Uani 1 1 d . . . . .
F7 F 0.32634(10) 0.52031(6) 0.92786(8) 0.0298(2) Uani 1 1 d . . . . .
C8 C 0.41353(14) 0.47172(8) 0.76617(13) 0.0207(3) Uani 1 1 d . . . . .
H8 H 0.4904(19) 0.4507(11) 0.8331(18) 0.025 Uiso 1 1 d . U . . .
C9 C 0.39952(13) 0.46420(8) 0.63438(13) 0.0179(2) Uani 1 1 d . . . . .
H9 H 0.4661(18) 0.4393(10) 0.6072(17) 0.022 Uiso 1 1 d . U . . .
C10 C 0.27822(13) 0.38776(7) 0.12172(12) 0.0153(2) Uani 1 1 d . . . . .
C11 C 0.17208(13) 0.38340(7) 0.00413(13) 0.0173(2) Uani 1 1 d . . . . .
F11 F 0.05978(8) 0.42649(5) -0.01734(8) 0.02603(19) Uani 1 1 d . . . . .
C12 C 0.17870(14) 0.33433(8) -0.09320(13) 0.0199(3) Uani 1 1 d . . . . .
F12 F 0.07501(9) 0.33120(5) -0.20633(8) 0.0284(2) Uani 1 1 d . . . . .
C13 C 0.29153(16) 0.28828(9) -0.07116(14) 0.0237(3) Uani 1 1 d . . . . .
F13 F 0.29416(11) 0.23900(6) -0.16542(9) 0.0342(2) Uani 1 1 d . . . . .
C14 C 0.39849(16) 0.29171(9) 0.04455(14) 0.0267(3) Uani 1 1 d . . . . .
H14 H 0.473(2) 0.2604(12) 0.057(2) 0.032 Uiso 1 1 d . U . . .
C15 C 0.39261(14) 0.34228(8) 0.14107(13) 0.0209(3) Uani 1 1 d . . . . .
H15 H 0.464(2) 0.3453(11) 0.2177(19) 0.025 Uiso 1 1 d . U . . .
C16 C 0.13740(14) 0.29370(8) 0.39815(14) 0.0223(3) Uani 1 1 d . . . . .
H16 H 0.062(2) 0.3266(11) 0.3605(19) 0.027 Uiso 1 1 d . U . . .
C17 C 0.18816(15) 0.23758(8) 0.32891(14) 0.0237(3) Uani 1 1 d . . . . .
H17 H 0.157(2) 0.2297(11) 0.239(2) 0.028 Uiso 1 1 d . U . . .
C18 C 0.29936(16) 0.20387(8) 0.42069(16) 0.0260(3) Uani 1 1 d . . . . .
H18 H 0.360(2) 0.1692(12) 0.400(2) 0.031 Uiso 1 1 d . U . . .
C19 C 0.31257(16) 0.23427(9) 0.54862(15) 0.0270(3) Uani 1 1 d . . . . .
H19 H 0.381(2) 0.2212(12) 0.626(2) 0.032 Uiso 1 1 d . U . . .
C20 C 0.20927(15) 0.28691(9) 0.53535(14) 0.0252(3) Uani 1 1 d . . . . .
H20 H 0.191(2) 0.3170(12) 0.598(2) 0.030 Uiso 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 Cl1 2.2059(4) . ?
Ni1 C1 1.8741(13) . ?
Ni1 C16 2.0368(14) . ?
Ni1 C17 2.1618(14) . ?
Ni1 C18 2.1527(14) . ?
Ni1 C19 2.1407(14) . ?
Ni1 C20 2.1370(14) . ?
N1 C1 1.3643(16) . ?
N1 C3 1.3979(16) . ?
N1 C4 1.4286(16) . ?
C1 N2 1.3604(16) . ?
N2 C2 1.3976(16) . ?
N2 C10 1.4273(16) . ?
C2 H2 0.941(18) . ?
C2 C3 1.3409(19) . ?
C3 H3 0.936(19) . ?
C4 C5 1.3855(18) . ?
C4 C9 1.3920(18) . ?
C5 F5 1.3448(15) . ?
C5 C6 1.3873(19) . ?
C6 F6 1.3413(16) . ?
C6 C7 1.380(2) . ?
C7 F7 1.3510(15) . ?
C7 C8 1.377(2) . ?
C8 H8 0.959(19) . ?
C8 C9 1.3914(19) . ?
C9 H9 0.941(18) . ?
C10 C11 1.3868(18) . ?
C10 C15 1.3886(18) . ?
C11 F11 1.3443(15) . ?
C11 C12 1.3815(19) . ?
C12 F12 1.3414(16) . ?
C12 C13 1.378(2) . ?
C13 F13 1.3467(16) . ?
C13 C14 1.377(2) . ?
C14 H14 0.92(2) . ?
C14 C15 1.389(2) . ?
C15 H15 0.91(2) . ?
C16 H16 0.95(2) . ?
C16 C17 1.439(2) . ?
C16 C20 1.433(2) . ?
C17 H17 0.93(2) . ?
C17 C18 1.386(2) . ?
C18 H18 0.95(2) . ?
C18 C19 1.448(2) . ?
C19 H19 0.93(2) . ?
C19 C20 1.388(2) . ?
C20 H20 0.93(2) . ?

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
C1 Ni1 Cl1 98.13(4) . . ?
C1 Ni1 C16 95.66(6) . . ?
C1 Ni1 C17 113.73(6) . . ?
C1 Ni1 C18 150.54(6) . . ?
C1 Ni1 C19 153.02(6) . . ?
C1 Ni1 C20 115.47(6) . . ?
C16 Ni1 Cl1 166.16(4) . . ?
C16 Ni1 C17 39.96(6) . . ?
C16 Ni1 C18 65.27(6) . . ?
C16 Ni1 C19 65.53(6) . . ?
C16 Ni1 C20 40.06(6) . . ?
C17 Ni1 Cl1 132.60(4) . . ?
C18 Ni1 Cl1 102.39(4) . . ?
C18 Ni1 C17 37.48(6) . . ?
C19 Ni1 Cl1 101.09(4) . . ?
C19 Ni1 C17 64.84(6) . . ?
C19 Ni1 C18 39.43(6) . . ?
C20 Ni1 Cl1 130.36(4) . . ?
C20 Ni1 C17 65.94(6) . . ?
C20 Ni1 C18 64.93(6) . . ?
C20 Ni1 C19 37.86(6) . . ?
C1 N1 C3 111.59(10) . . ?
C1 N1 C4 123.91(11) . . ?
C3 N1 C4 124.50(11) . . ?
N1 C1 Ni1 128.95(9) . . ?
N2 C1 Ni1 127.44(9) . . ?
N2 C1 N1 103.55(10) . . ?
C1 N2 C2 111.61(11) . . ?
C1 N2 C10 124.51(11) . . ?
C2 N2 C10 123.88(11) . . ?
N2 C2 H2 121.1(11) . . ?
C3 C2 N2 106.72(11) . . ?
C3 C2 H2 132.1(11) . . ?
N1 C3 H3 120.6(11) . . ?
C2 C3 N1 106.53(11) . . ?
C2 C3 H3 132.8(11) . . ?
C5 C4 N1 119.96(11) . . ?
C5 C4 C9 119.19(12) . . ?
C9 C4 N1 120.85(11) . . ?
C4 C5 C6 120.54(12) . . ?
F5 C5 C4 121.33(12) . . ?
F5 C5 C6 118.14(12) . . ?
F6 C6 C5 120.05(13) . . ?
F6 C6 C7 120.56(13) . . ?
C7 C6 C5 119.39(13) . . ?
F7 C7 C6 117.92(13) . . ?
F7 C7 C8 120.84(13) . . ?
C8 C7 C6 121.25(13) . . ?
C7 C8 H8 119.5(11) . . ?
C7 C8 C9 119.08(13) . . ?
C9 C8 H8 121.4(11) . . ?
C4 C9 H9 118.0(11) . . ?
C8 C9 C4 120.55(12) . . ?
C8 C9 H9 121.4(11) . . ?
C11 C10 N2 119.44(11) . . ?
C11 C10 C15 119.27(12) . . ?
C15 C10 N2 121.29(12) . . ?
F11 C11 C10 120.67(12) . . ?
F11 C11 C12 118.45(12) . . ?
C12 C11 C10 120.87(12) . . ?
F12 C12 C11 119.86(12) . . ?
F12 C12 C13 121.04(12) . . ?
C13 C12 C11 119.09(13) . . ?
F13 C13 C12 118.27(13) . . ?
F13 C13 C14 120.57(13) . . ?
C14 C13 C12 121.16(13) . . ?
C13 C14 H14 119.6(13) . . ?
C13 C14 C15 119.53(13) . . ?
C15 C14 H14 120.9(13) . . ?
C10 C15 C14 120.05(13) . . ?
C10 C15 H15 119.8(12) . . ?
C14 C15 H15 120.1(12) . . ?
Ni1 C16 H16 122.8(12) . . ?
C17 C16 Ni1 74.70(8) . . ?
C17 C16 H16 125.7(12) . . ?
C20 C16 Ni1 73.73(8) . . ?
C20 C16 H16 125.0(12) . . ?
C20 C16 C17 109.07(13) . . ?
Ni1 C17 H17 123.8(12) . . ?
C16 C17 Ni1 65.34(7) . . ?
C16 C17 H17 125.7(12) . . ?
C18 C17 Ni1 70.90(8) . . ?
C18 C17 C16 106.31(13) . . ?
C18 C17 H17 127.7(12) . . ?
Ni1 C18 H18 121.1(12) . . ?
C17 C18 Ni1 71.61(8) . . ?
C17 C18 H18 124.3(12) . . ?
C17 C18 C19 108.92(13) . . ?
C19 C18 Ni1 69.84(8) . . ?
C19 C18 H18 126.6(12) . . ?
Ni1 C19 H19 122.9(13) . . ?
C18 C19 Ni1 70.73(8) . . ?
C18 C19 H19 124.9(13) . . ?
C20 C19 Ni1 70.92(8) . . ?
C20 C19 C18 108.55(13) . . ?
C20 C19 H19 126.5(13) . . ?
Ni1 C20 H20 122.9(12) . . ?
C16 C20 Ni1 66.20(8) . . ?
C16 C20 H20 123.3(13) . . ?
C19 C20 Ni1 71.22(8) . . ?
C19 C20 C16 106.66(13) . . ?
C19 C20 H20 129.8(13) . . ?

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 C1 N2 C2 177.07(9) . . . . ?
Ni1 C1 N2 C10 -3.06(18) . . . . ?
Ni1 C16 C17 C18 59.38(10) . . . . ?
Ni1 C16 C20 C19 -60.05(10) . . . . ?
Ni1 C17 C18 C19 60.14(10) . . . . ?
Ni1 C18 C19 C20 61.15(10) . . . . ?
Ni1 C19 C20 C16 56.86(10) . . . . ?
Cl1 Ni1 C1 N1 -93.83(11) . . . . ?
Cl1 Ni1 C1 N2 89.52(11) . . . . ?
N1 C1 N2 C2 -0.25(13) . . . . ?
N1 C1 N2 C10 179.62(11) . . . . ?
N1 C4 C5 F5 -0.39(19) . . . . ?
N1 C4 C5 C6 179.32(12) . . . . ?
N1 C4 C9 C8 -179.27(12) . . . . ?
C1 N1 C3 C2 -0.30(15) . . . . ?
C1 N1 C4 C5 -134.93(13) . . . . ?
C1 N1 C4 C9 44.80(18) . . . . ?
C1 N2 C2 C3 0.08(15) . . . . ?
C1 N2 C10 C11 130.44(13) . . . . ?
C1 N2 C10 C15 -49.99(18) . . . . ?
N2 C2 C3 N1 0.13(14) . . . . ?
N2 C10 C11 F11 -0.67(19) . . . . ?
N2 C10 C11 C12 179.84(12) . . . . ?
N2 C10 C15 C14 178.83(13) . . . . ?
C2 N2 C10 C11 -49.71(17) . . . . ?
C2 N2 C10 C15 129.86(14) . . . . ?
C3 N1 C1 Ni1 -176.93(9) . . . . ?
C3 N1 C1 N2 0.34(14) . . . . ?
C3 N1 C4 C5 46.01(18) . . . . ?
C3 N1 C4 C9 -134.26(13) . . . . ?
C4 N1 C1 Ni1 3.90(18) . . . . ?
C4 N1 C1 N2 -178.83(11) . . . . ?
C4 N1 C3 C2 178.86(11) . . . . ?
C4 C5 C6 F6 -178.80(12) . . . . ?
C4 C5 C6 C7 0.6(2) . . . . ?
C5 C4 C9 C8 0.5(2) . . . . ?
C5 C6 C7 F7 178.98(12) . . . . ?
C5 C6 C7 C8 -0.8(2) . . . . ?
F5 C5 C6 F6 0.9(2) . . . . ?
F5 C5 C6 C7 -179.70(12) . . . . ?
C6 C7 C8 C9 0.8(2) . . . . ?
F6 C6 C7 F7 -1.6(2) . . . . ?
F6 C6 C7 C8 178.58(13) . . . . ?
C7 C8 C9 C4 -0.7(2) . . . . ?
F7 C7 C8 C9 -178.93(12) . . . . ?
C9 C4 C5 F5 179.87(12) . . . . ?
C9 C4 C5 C6 -0.4(2) . . . . ?
C10 N2 C2 C3 -179.79(11) . . . . ?
C10 C11 C12 F12 -179.81(12) . . . . ?
C10 C11 C12 C13 1.3(2) . . . . ?
C11 C10 C15 C14 -1.6(2) . . . . ?
C11 C12 C13 F13 177.79(13) . . . . ?
C11 C12 C13 C14 -1.5(2) . . . . ?
F11 C11 C12 F12 0.69(19) . . . . ?
F11 C11 C12 C13 -178.21(13) . . . . ?
C12 C13 C14 C15 0.2(2) . . . . ?
F12 C12 C13 F13 -1.1(2) . . . . ?
F12 C12 C13 C14 179.59(14) . . . . ?
C13 C14 C15 C10 1.4(2) . . . . ?
F13 C13 C14 C15 -179.10(14) . . . . ?
C15 C10 C11 F11 179.75(12) . . . . ?
C15 C10 C11 C12 0.3(2) . . . . ?
C16 Ni1 C1 N1 85.02(12) . . . . ?
C16 Ni1 C1 N2 -91.63(12) . . . . ?
C16 C17 C18 Ni1 -55.85(9) . . . . ?
C16 C17 C18 C19 4.29(16) . . . . ?
C17 Ni1 C1 N1 122.10(11) . . . . ?
C17 Ni1 C1 N2 -54.55(12) . . . . ?
C17 C16 C20 Ni1 66.94(10) . . . . ?
C17 C16 C20 C19 6.89(16) . . . . ?
C17 C18 C19 Ni1 -61.24(10) . . . . ?
C17 C18 C19 C20 -0.09(17) . . . . ?
C18 Ni1 C1 N1 132.23(13) . . . . ?
C18 Ni1 C1 N2 -44.42(18) . . . . ?
C18 C19 C20 Ni1 -61.03(10) . . . . ?
C18 C19 C20 C16 -4.17(16) . . . . ?
C19 Ni1 C1 N1 41.32(19) . . . . ?
C19 Ni1 C1 N2 -135.33(13) . . . . ?
C20 Ni1 C1 N1 48.60(13) . . . . ?
C20 Ni1 C1 N2 -128.05(11) . . . . ?
C20 C16 C17 Ni1 -66.31(10) . . . . ?
C20 C16 C17 C18 -6.93(16) . . . . ?

_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 1.575
_oxdiff_exptl_absorpt_empirical_full_min 0.837


####################################################################### 
# 
# 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_DPR553
_database_code_depnum_ccdc_archive 'CCDC 2362711'
loop_
_audit_author_name
_audit_author_address
'Mikhail Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2024-06-13 deposited with the CCDC.	2024-07-16 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT911_DPR553              
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         58 Report
RESPONSE: Some reflections were not collected or were omitted during
 the integration due to relatively poor crystal quality, weak diffraction
 ability, high mosaicity, and minor unidentified twinning.
;
# end Validation Reply Form
_audit_creation_date             2024-06-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H11 F4 N3 O2 Pd'
_chemical_formula_sum            'C20 H11 F4 N3 O2 Pd'
_chemical_formula_weight         507.72
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H11F4N3O2Pd
_chemical_oxdiff_usercomment     PDO-553-Pd
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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd 0.1215 3.9337 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.68882(7)
_cell_length_b                   11.4296(2)
_cell_length_c                   20.0470(3)
_cell_angle_alpha                88.7087(14)
_cell_angle_beta                 84.9983(14)
_cell_angle_gamma                82.4843(17)
_cell_volume                     834.71(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7596
_cell_measurement_temperature    100.00(11)
_cell_measurement_theta_max      79.2340
_cell_measurement_theta_min      2.1860
_shelx_estimated_absorpt_T_max   0.831
_shelx_estimated_absorpt_T_min   0.513
_exptl_absorpt_coefficient_mu    9.614
_exptl_absorpt_correction_T_max  0.888
_exptl_absorpt_correction_T_min  0.551
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.125a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear red'
_exptl_crystal_density_diffrn    2.020
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             500
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0097
0 0 -1 0.0161
0 0 1 0.0148
-1 0 0 0.0380
1 0 0 0.0418
0 -1 -2 0.0153
0 1 1 0.0102
0 -1 1 0.0145
0 1 -1 0.0120

_exptl_crystal_size_max          0.085
_exptl_crystal_size_mid          0.031
_exptl_crystal_size_min          0.022
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0001 -1.0004 -0.0003 0.0006 -0.1353 -0.0142
0.0001 0.0002 -1.0000 -0.0568 -0.0049 0.0520
-0.0001 -0.0002 1.0000 0.0568 0.0049 -0.0520
-0.9999 0.0016 -0.0002 0.3093 0.0263 0.2870
0.9999 -0.0016 0.0002 -0.3093 -0.0263 -0.2870
0.0001 -1.0000 -2.0003 -0.1130 -0.1450 0.0897
0.0000 1.0002 1.0003 0.0562 0.1401 -0.0377
-0.0002 -1.0005 0.9997 0.0574 -0.1304 -0.0662
0.0002 1.0005 -0.9997 -0.0574 0.1304 0.0662

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12853
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.654
_diffrn_reflns_theta_min         2.212
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -51.00  -6.00   0.50    3.00    --  -46.47  64.00  73.00   90
  2  ω    -78.00 -44.00   0.50    3.00    --  -46.47 -64.00 -63.00   68
  3  ω     68.00 102.00   0.50    3.00    --   46.47  64.00  73.00   68
  4  ω     20.00  45.00   0.50    3.00    --   46.47 -64.00 -63.00   50
  5  ω   -144.00-118.00   0.50   12.00    --  -91.75 -64.00 -63.00   52
  6  ω    -72.00 -47.00   0.50   12.00    --  -91.75  64.00  73.00   50
  7  ω     98.00 140.00   0.50   12.00    --  113.25  64.00  73.00   84
  8  ω     41.00  66.00   0.50   12.00    --  113.25 -64.00 -63.00   50
  9  ω     -7.00  28.00   0.50    3.00    --  -46.47  19.00-150.00   70
 10  ω    -54.00 -15.00   0.50    3.00    --  -46.47 125.00-180.00   78
 11  ω    -26.00  28.00   0.50    3.00    --  -46.47  19.00 -60.00  108
 12  ω    -25.00  28.00   0.50    3.00    --  -46.47  19.00-180.00  106
 13  ω    -72.00 -32.00   0.50    3.00    --  -46.47 -38.00-180.00   80
 14  ω     34.00 120.00   0.50    3.00    --   46.47  38.00-150.00  172
 15  ω     39.00  87.00   0.50    3.00    --   46.47-125.00 150.00   96
 16  ω   -137.00 -73.00   0.50   12.00    --  -91.75 -65.00 165.82  128
 17  ω    -93.00 -68.00   0.50   12.00    --  -91.75 -77.00-150.00   50
 18  ω     44.00  70.00   0.50   12.00    --  113.25 -61.00-150.00   52
 19  ω    140.00 177.00   0.50   12.00    --  113.25  61.00 120.00   74
 20  ω     76.00 102.00   0.50   12.00    --  113.25 -81.00 109.81   52
 21  ω     94.00 123.00   0.50   12.00    --  113.25  77.00 150.00   58
 22  ω    139.00 172.00   0.50   12.00    --  113.25  77.00 150.00   66
 23  ω     43.00  69.00   0.50   12.00    --  113.25 -77.00 120.00   52
 24  ω     99.00 151.00   0.50   12.00    --  113.25  30.00  30.00  104
 25  ω    103.00 129.00   0.50   12.00    --  113.25 -88.00 114.58   52
 26  ω     90.00 115.00   0.50   12.00    --  113.25  77.00-150.00   50
 27  ω     85.00 126.00   0.50   12.00    --  113.25 -88.00-136.75   82
 28  ω     66.00  92.00   0.50   12.00    --  113.25 -88.00 114.58   52
 29  ω    132.00 165.00   0.50   12.00    --  113.25  77.00-150.00   66
 30  ω    152.00 177.00   0.50   12.00    --  113.25  30.00-150.00   50
 31  ω    105.00 139.00   0.50   12.00    --  113.25 -81.00 109.81   68
 32  ω     71.00 102.00   0.50   12.00    --  113.25 -77.00 120.00   62
 33  ω     42.00  98.00   0.50   12.00    --  113.25 -95.00  30.00  112
 34  ω    122.00 148.00   0.50   12.00    --  113.25  45.00-150.00   52
 35  ω     96.00 178.00   0.50   12.00    --  113.25  15.00   0.00  164
 36  ω    103.00 129.00   0.50   12.00    --  113.25 125.00 150.00   52
 37  ω    101.00 127.00   0.50   12.00    --  113.25  30.00  90.00   52
 38  ω    129.00 155.00   0.50   12.00    --  113.25 125.00 120.00   52
 39  ω     41.00  69.00   0.50   12.00    --  113.25 -61.00 150.00   56
 40  ω    150.00 176.00   0.50   12.00    --  113.25  77.00  30.00   52
 41  ω     90.00 145.00   0.50   12.00    --  113.25  77.00-180.00  110
 42  ω     43.00  98.00   0.50   12.00    --  113.25 -77.00  30.00  110
 43  ω    111.00 137.00   0.50   12.00    --  113.25  61.00-180.00   52
 44  ω     75.00 100.00   0.50   12.00    --  113.25 -77.00 -90.00   50
 45  ω    149.00 177.00   0.50   12.00    --  113.25  77.00-180.00   56
 46  ω     43.00  69.00   0.50   12.00    --  113.25-125.00   0.00   52
 47  ω    153.00 178.00   0.50   12.00    --  113.25 125.00 -60.00   50
 48  ω     55.00  87.00   0.50   12.00    --  113.25 -77.00-150.00   64
 49  ω     45.00  83.00   0.50   12.00    --  113.25-125.00 150.00   76
 50  ω    134.00 177.00   0.50   12.00    --  113.25  45.00  60.00   86
 51  ω    108.00 133.00   0.50   12.00    --  113.25  30.00-180.00   50
 52  ω    110.00 135.00   0.50   12.00    --  113.25  30.00-150.00   50
 53  ω     95.00 134.00   0.50   12.00    --  113.25 125.00 -60.00   78
 54  ω     42.00  69.00   0.50   12.00    --  113.25 -61.00 -60.00   54
 55  ω    130.00 163.00   0.50   12.00    --  113.25  15.00 -30.00   66
 56  ω     45.00 113.00   0.50   12.00    --  113.25 -88.00 -14.30  136
 57  ω     42.00  76.00   0.50   12.00    --  113.25 -77.00 -60.00   68
 58  ω     62.00 105.00   0.50   12.00    --  113.25 -77.00  60.00   86
 59  ω     96.00 138.00   0.50   12.00    --  113.25  61.00-150.00   84
 60  ω     41.00  69.00   0.50   12.00    --  113.25 -61.00 -30.00   56
 61  ω    153.00 178.00   0.50   12.00    --  113.25  15.00-180.00   50
 62  ω    123.00 178.00   0.50   12.00    --  113.25  45.00 -90.00  110
 63  ω     99.00 132.00   0.50   12.00    --  113.25  45.00 -60.00   66
 64  ω    149.00 175.00   0.50   12.00    --  113.25  45.00 -60.00   52
 65  ω    102.00 127.00   0.50   12.00    --  113.25  45.00 120.00   50
 66  ω    134.00 160.00   0.50   12.00    --  113.25  45.00 120.00   52
 67  ω    101.00 142.00   0.50   12.00    --  113.25  30.00 -90.00   82
 68  ω    151.00 178.00   0.50   12.00    --  113.25  30.00 150.00   54
 69  ω    121.00 147.00   0.50   12.00    --  113.25  61.00  30.00   52
 70  ω     91.00 122.00   0.50   12.00    --  113.25  77.00-120.00   62
 71  ω     97.00 137.00   0.50   12.00    --  113.25  15.00-180.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.3093445000
_diffrn_orient_matrix_UB_12      -0.0006216000
_diffrn_orient_matrix_UB_13      0.0567851000
_diffrn_orient_matrix_UB_21      -0.0260999000
_diffrn_orient_matrix_UB_22      0.1352095000
_diffrn_orient_matrix_UB_23      0.0048789000
_diffrn_orient_matrix_UB_31      -0.2869961000
_diffrn_orient_matrix_UB_32      0.0142829000
_diffrn_orient_matrix_UB_33      -0.0519920000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3248
_reflns_number_total             3473
_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 1.171.43.125a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.124a 64-bit (release 23-05-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.125a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL  (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         1.140
_refine_diff_density_min         -0.884
_refine_diff_density_rms         0.109
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         3473
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0312
_refine_ls_restrained_S_all      1.094
_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)+3.8844P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0743
_refine_ls_wR_factor_ref         0.0754
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
Pd1 Pd 0.70353(7) 0.41201(2) 0.28023(2) 0.01384(8) Uani 1 1 d . . . . .
N1 N 0.8614(8) 0.6130(3) 0.19468(15) 0.0180(6) Uani 1 1 d . . . . .
C1 C 0.8598(9) 0.4945(3) 0.20068(18) 0.0157(7) Uani 1 1 d . . . . .
N2 N 1.0249(8) 0.4465(3) 0.14258(15) 0.0168(6) Uani 1 1 d . . . . .
C2 C 1.1402(10) 0.5380(4) 0.10108(19) 0.0205(7) Uani 1 1 d . . . . .
H2 H 1.257(13) 0.525(4) 0.057(2) 0.025 Uiso 1 1 d . U . . .
C3 C 1.0398(11) 0.6394(4) 0.13321(19) 0.0213(8) Uani 1 1 d . . . . .
H3 H 1.081(13) 0.713(5) 0.120(2) 0.026 Uiso 1 1 d . U . . .
C4 C 0.6753(10) 0.6964(3) 0.24270(18) 0.0171(7) Uani 1 1 d . . . . .
C5 C 0.5970(10) 0.6615(3) 0.31025(18) 0.0170(7) Uani 1 1 d . . . . .
O5 O 0.6962(7) 0.5562(2) 0.33469(13) 0.0200(5) Uani 1 1 d . . . . .
C6 C 0.4064(10) 0.7476(3) 0.35458(19) 0.0200(7) Uani 1 1 d . . . . .
H6 H 0.354(13) 0.729(4) 0.398(2) 0.024 Uiso 1 1 d . U . . .
C7 C 0.2998(10) 0.8592(3) 0.3317(2) 0.0207(8) Uani 1 1 d . . . . .
F7 F 0.1097(6) 0.9387(2) 0.37628(12) 0.0267(5) Uani 1 1 d . . . . .
C8 C 0.3674(11) 0.8959(3) 0.2666(2) 0.0212(8) Uani 1 1 d . . . . .
H8 H 0.294(13) 0.972(5) 0.251(2) 0.025 Uiso 1 1 d . U . . .
C9 C 0.5516(11) 0.8118(3) 0.22363(18) 0.0197(7) Uani 1 1 d . . . . .
F9 F 0.6073(7) 0.8450(2) 0.15840(11) 0.0274(5) Uani 1 1 d . . . . .
C10 C 1.0538(10) 0.3237(3) 0.12640(18) 0.0166(7) Uani 1 1 d . . . . .
C11 C 0.9016(10) 0.2411(3) 0.17129(17) 0.0162(7) Uani 1 1 d . . . . .
O11 O 0.7299(7) 0.2634(2) 0.23045(13) 0.0200(5) Uani 1 1 d . . . . .
C12 C 0.9269(10) 0.1227(3) 0.15030(18) 0.0180(7) Uani 1 1 d . . . . .
H12 H 0.830(13) 0.064(4) 0.181(2) 0.022 Uiso 1 1 d . U . . .
C13 C 1.0895(10) 0.0891(3) 0.08863(18) 0.0188(7) Uani 1 1 d . . . . .
F13 F 1.1016(7) -0.0251(2) 0.07043(11) 0.0252(5) Uani 1 1 d . . . . .
C14 C 1.2434(11) 0.1661(4) 0.04389(18) 0.0208(8) Uani 1 1 d . . . . .
H14 H 1.362(13) 0.143(4) 0.003(2) 0.025 Uiso 1 1 d . U . . .
C15 C 1.2222(10) 0.2806(4) 0.06507(17) 0.0190(7) Uani 1 1 d . . . . .
F15 F 1.3799(7) 0.3552(2) 0.02030(11) 0.0254(5) Uani 1 1 d . . . . .
N3 N 0.5331(8) 0.3227(3) 0.36874(15) 0.0162(6) Uani 1 1 d . . . . .
C16 C 0.5940(10) 0.2050(3) 0.37430(19) 0.0194(7) Uani 1 1 d . . . . .
H16 H 0.700(13) 0.164(4) 0.334(2) 0.023 Uiso 1 1 d . U . . .
C17 C 0.4850(11) 0.1449(3) 0.43179(19) 0.0197(7) Uani 1 1 d . . . . .
H17 H 0.524(13) 0.063(5) 0.430(2) 0.024 Uiso 1 1 d . U . . .
C18 C 0.3079(10) 0.2085(4) 0.48581(18) 0.0198(7) Uani 1 1 d . . . . .
H18 H 0.231(13) 0.164(4) 0.522(2) 0.024 Uiso 1 1 d . U . . .
C19 C 0.2454(10) 0.3304(4) 0.48052(19) 0.0213(8) Uani 1 1 d . . . . .
H19 H 0.130(13) 0.380(4) 0.518(2) 0.026 Uiso 1 1 d . U . . .
C20 C 0.3608(10) 0.3843(3) 0.42127(18) 0.0192(7) Uani 1 1 d . . . . .
H20 H 0.333(13) 0.464(5) 0.417(2) 0.023 Uiso 1 1 d . 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
Pd1 C1 1.918(4) . ?
Pd1 O5 1.994(3) . ?
Pd1 O11 1.977(3) . ?
Pd1 N3 2.116(3) . ?
N1 C1 1.358(5) . ?
N1 C3 1.392(5) . ?
N1 C4 1.436(5) . ?
C1 N2 1.359(4) . ?
N2 C2 1.407(5) . ?
N2 C10 1.437(5) . ?
C2 H2 0.96(5) . ?
C2 C3 1.333(6) . ?
C3 H3 0.90(5) . ?
C4 C5 1.419(5) . ?
C4 C9 1.395(5) . ?
C5 O5 1.308(4) . ?
C5 C6 1.415(5) . ?
C6 H6 0.91(5) . ?
C6 C7 1.366(6) . ?
C7 F7 1.369(4) . ?
C7 C8 1.374(6) . ?
C8 H8 0.94(5) . ?
C8 C9 1.376(5) . ?
C9 F9 1.359(4) . ?
C10 C11 1.424(5) . ?
C10 C15 1.398(5) . ?
C11 O11 1.309(4) . ?
C11 C12 1.415(5) . ?
C12 H12 0.98(5) . ?
C12 C13 1.367(5) . ?
C13 F13 1.357(4) . ?
C13 C14 1.381(5) . ?
C14 H14 0.93(5) . ?
C14 C15 1.376(6) . ?
C15 F15 1.369(4) . ?
N3 C16 1.338(5) . ?
N3 C20 1.345(5) . ?
C16 H16 0.97(5) . ?
C16 C17 1.385(5) . ?
C17 H17 0.93(5) . ?
C17 C18 1.384(5) . ?
C18 H18 0.92(5) . ?
C18 C19 1.386(6) . ?
C19 H19 0.99(5) . ?
C19 C20 1.385(5) . ?
C20 H20 0.91(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
C1 Pd1 O5 90.88(13) . . ?
C1 Pd1 O11 91.42(13) . . ?
C1 Pd1 N3 179.28(14) . . ?
O5 Pd1 N3 88.42(11) . . ?
O11 Pd1 O5 176.35(12) . . ?
O11 Pd1 N3 89.26(11) . . ?
C1 N1 C3 109.5(3) . . ?
C1 N1 C4 123.8(3) . . ?
C3 N1 C4 126.4(3) . . ?
N1 C1 Pd1 125.6(3) . . ?
N1 C1 N2 106.8(3) . . ?
N2 C1 Pd1 127.3(3) . . ?
C1 N2 C2 108.4(3) . . ?
C1 N2 C10 124.5(3) . . ?
C2 N2 C10 127.0(3) . . ?
N2 C2 H2 123(3) . . ?
C3 C2 N2 107.9(3) . . ?
C3 C2 H2 129(3) . . ?
N1 C3 H3 124(3) . . ?
C2 C3 N1 107.3(3) . . ?
C2 C3 H3 128(3) . . ?
C5 C4 N1 120.6(3) . . ?
C9 C4 N1 121.0(3) . . ?
C9 C4 C5 118.3(3) . . ?
O5 C5 C4 124.6(3) . . ?
O5 C5 C6 117.8(3) . . ?
C6 C5 C4 117.6(3) . . ?
C5 O5 Pd1 121.3(2) . . ?
C5 C6 H6 120(3) . . ?
C7 C6 C5 120.1(4) . . ?
C7 C6 H6 120(3) . . ?
C6 C7 F7 117.9(3) . . ?
C6 C7 C8 123.9(4) . . ?
F7 C7 C8 118.2(3) . . ?
C7 C8 H8 124(3) . . ?
C7 C8 C9 115.8(3) . . ?
C9 C8 H8 120(3) . . ?
C8 C9 C4 124.2(3) . . ?
F9 C9 C4 119.1(3) . . ?
F9 C9 C8 116.6(3) . . ?
C11 C10 N2 121.4(3) . . ?
C15 C10 N2 121.5(3) . . ?
C15 C10 C11 117.1(3) . . ?
O11 C11 C10 126.7(3) . . ?
O11 C11 C12 115.4(3) . . ?
C12 C11 C10 117.9(3) . . ?
C11 O11 Pd1 126.0(2) . . ?
C11 C12 H12 119(3) . . ?
C13 C12 C11 120.9(3) . . ?
C13 C12 H12 120(3) . . ?
C12 C13 C14 123.0(4) . . ?
F13 C13 C12 118.7(3) . . ?
F13 C13 C14 118.3(3) . . ?
C13 C14 H14 123(3) . . ?
C15 C14 C13 115.7(3) . . ?
C15 C14 H14 121(3) . . ?
C14 C15 C10 125.4(3) . . ?
F15 C15 C10 119.8(3) . . ?
F15 C15 C14 114.8(3) . . ?
C16 N3 Pd1 121.6(2) . . ?
C16 N3 C20 118.4(3) . . ?
C20 N3 Pd1 120.0(2) . . ?
N3 C16 H16 116(3) . . ?
N3 C16 C17 122.5(3) . . ?
C17 C16 H16 122(3) . . ?
C16 C17 H17 117(3) . . ?
C18 C17 C16 119.0(4) . . ?
C18 C17 H17 124(3) . . ?
C17 C18 H18 116(3) . . ?
C17 C18 C19 118.8(3) . . ?
C19 C18 H18 125(3) . . ?
C18 C19 H19 122(3) . . ?
C20 C19 C18 118.9(3) . . ?
C20 C19 H19 119(3) . . ?
N3 C20 C19 122.4(4) . . ?
N3 C20 H20 116(3) . . ?
C19 C20 H20 121(3) . . ?

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
Pd1 C1 N2 C2 -171.6(3) . . . . ?
Pd1 C1 N2 C10 11.6(5) . . . . ?
Pd1 N3 C16 C17 180.0(3) . . . . ?
Pd1 N3 C20 C19 -179.6(3) . . . . ?
N1 C1 N2 C2 1.9(4) . . . . ?
N1 C1 N2 C10 -174.9(3) . . . . ?
N1 C4 C5 O5 2.9(6) . . . . ?
N1 C4 C5 C6 -178.7(3) . . . . ?
N1 C4 C9 C8 179.1(4) . . . . ?
N1 C4 C9 F9 0.3(5) . . . . ?
C1 N1 C3 C2 1.3(4) . . . . ?
C1 N1 C4 C5 24.4(5) . . . . ?
C1 N1 C4 C9 -152.5(4) . . . . ?
C1 N2 C2 C3 -1.1(4) . . . . ?
C1 N2 C10 C11 1.0(5) . . . . ?
C1 N2 C10 C15 178.9(3) . . . . ?
N2 C2 C3 N1 -0.1(4) . . . . ?
N2 C10 C11 O11 -1.2(6) . . . . ?
N2 C10 C11 C12 177.1(3) . . . . ?
N2 C10 C15 C14 -176.1(4) . . . . ?
N2 C10 C15 F15 3.2(5) . . . . ?
C2 N2 C10 C11 -175.3(4) . . . . ?
C2 N2 C10 C15 2.6(6) . . . . ?
C3 N1 C1 Pd1 171.6(3) . . . . ?
C3 N1 C1 N2 -2.0(4) . . . . ?
C3 N1 C4 C5 -161.7(4) . . . . ?
C3 N1 C4 C9 21.4(6) . . . . ?
C4 N1 C1 Pd1 -13.6(5) . . . . ?
C4 N1 C1 N2 172.8(3) . . . . ?
C4 N1 C3 C2 -173.3(4) . . . . ?
C4 C5 O5 Pd1 -36.0(5) . . . . ?
C4 C5 C6 C7 0.9(5) . . . . ?
C5 C4 C9 C8 2.2(6) . . . . ?
C5 C4 C9 F9 -176.6(3) . . . . ?
C5 C6 C7 F7 178.7(3) . . . . ?
C5 C6 C7 C8 -0.3(6) . . . . ?
O5 C5 C6 C7 179.4(3) . . . . ?
C6 C5 O5 Pd1 145.7(3) . . . . ?
C6 C7 C8 C9 0.6(6) . . . . ?
C7 C8 C9 C4 -1.5(6) . . . . ?
C7 C8 C9 F9 177.3(3) . . . . ?
F7 C7 C8 C9 -178.5(3) . . . . ?
C9 C4 C5 O5 179.9(4) . . . . ?
C9 C4 C5 C6 -1.8(5) . . . . ?
C10 N2 C2 C3 175.6(4) . . . . ?
C10 C11 O11 Pd1 -10.6(5) . . . . ?
C10 C11 C12 C13 -0.6(5) . . . . ?
C11 C10 C15 C14 1.9(6) . . . . ?
C11 C10 C15 F15 -178.8(3) . . . . ?
C11 C12 C13 F13 -178.9(3) . . . . ?
C11 C12 C13 C14 1.2(6) . . . . ?
O11 C11 C12 C13 177.9(3) . . . . ?
C12 C11 O11 Pd1 171.1(2) . . . . ?
C12 C13 C14 C15 -0.3(6) . . . . ?
C13 C14 C15 C10 -1.4(6) . . . . ?
C13 C14 C15 F15 179.3(3) . . . . ?
F13 C13 C14 C15 179.9(3) . . . . ?
C15 C10 C11 O11 -179.2(3) . . . . ?
C15 C10 C11 C12 -0.9(5) . . . . ?
N3 C16 C17 C18 -0.3(6) . . . . ?
C16 N3 C20 C19 0.0(6) . . . . ?
C16 C17 C18 C19 0.0(6) . . . . ?
C17 C18 C19 C20 0.3(6) . . . . ?
C18 C19 C20 N3 -0.3(6) . . . . ?
C20 N3 C16 C17 0.3(6) . . . . ?

_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 1.262
_oxdiff_exptl_absorpt_empirical_full_min 0.921
####################################################################### 
# 
# 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_DPR557
_database_code_depnum_ccdc_archive 'CCDC 2362710'
loop_
_audit_author_name
_audit_author_address
'Mikhail Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2024-06-13 deposited with the CCDC.	2024-07-16 downloaded from the CCDC.
;
_audit_creation_date             2024-06-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H15 Cl F2 N2 Ni, 0.501(H2 O)'
_chemical_formula_sum            'C20 H16 Cl F2 N2 Ni O0.50'
_chemical_formula_weight         424.51
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H16.00 Cl F2 N2 Ni O0.50'
_chemical_oxdiff_usercomment     DPR557
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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'
O O 0.0492 0.0322 '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                   8.53819(6)
_cell_length_b                   18.09252(12)
_cell_length_c                   12.13920(8)
_cell_angle_alpha                90
_cell_angle_beta                 105.5562(7)
_cell_angle_gamma                90
_cell_volume                     1806.54(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17122
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      80.0190
_cell_measurement_theta_min      3.7890
_shelx_estimated_absorpt_T_max   0.764
_shelx_estimated_absorpt_T_min   0.270
_exptl_absorpt_coefficient_mu    3.167
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.287
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.125a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear red'
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             868
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.1434
0 1 0 0.2125
-1 -2 2 0.2260
-1 0 0 0.0383
1 0 0 0.0483
-1 0 2 0.2545
-2 -1 0 0.0503
-1 2 2 0.2455
2 0 -1 0.1001
-1 1 0 0.0991
1 0 1 0.1796
2 1 -1 0.0986
-1 0 -2 0.2007
1 -2 -1 0.1870
0 -1 1 0.2471
0 2 -1 0.1650
0 1 -2 0.2128
0 1 2 0.2715
1 2 -2 0.1592
-3 -5 1 0.0919
5 -2 0 0.0512

_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.09
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0000 -1.0000 -0.0000 0.0671 -0.0142 0.0505
0.0000 1.0000 0.0000 -0.0671 0.0142 -0.0505
-1.0000 -2.0000 2.0000 0.3024 -0.0272 -0.1219
-1.0000 -0.0000 0.0000 0.0694 0.1681 -0.0446
1.0000 0.0000 -0.0000 -0.0694 -0.1681 0.0446
-1.0000 -0.0000 2.0000 0.1683 0.0013 -0.2229
-2.0000 -1.0000 -0.0000 0.2059 0.3220 -0.0387
-1.0000 2.0000 2.0000 0.0342 0.0298 -0.3240
2.0000 0.0000 -1.0000 -0.1883 -0.2528 0.1784
-1.0000 1.0000 0.0000 0.0024 0.1824 -0.0951
1.0000 -0.0000 1.0000 -0.0200 -0.2515 -0.0446
2.0000 1.0000 -1.0000 -0.2554 -0.2386 0.1279
-1.0000 0.0000 -2.0000 -0.0295 0.3349 0.1337
1.0000 -2.0000 -1.0000 0.0152 -0.1132 0.2348
0.0000 -1.0000 1.0000 0.1165 -0.0977 -0.0386
0.0000 2.0000 -1.0000 -0.1836 0.1119 -0.0119
-0.0000 1.0000 -2.0000 -0.1660 0.1811 0.1278
0.0000 1.0000 2.0000 0.0318 -0.1526 -0.2288
1.0000 2.0000 -2.0000 -0.3024 0.0272 0.1219
-3.0000 -5.0000 1.0000 0.5930 0.3497 0.0296
5.0000 -2.0000 -0.0000 -0.2131 -0.8691 0.3241

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            26603
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.311
_diffrn_reflns_theta_min         4.502
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -32.00  76.00   0.50    0.05    --    0.00  72.00-127.00  216
  2  ω    -32.00  76.00   0.50    0.05    --    0.00  72.00-127.00  216
  3  ω      9.00 117.00   0.50    0.15    --   41.38  72.00-127.00  216
  4  ω     45.00 101.00   0.50    0.25    --  121.50-111.00-120.00  112
  5  ω     45.00 108.00   0.50    0.25    --  121.50-111.00 -60.00  126
  6  ω     46.00  72.00   0.50    0.25    --  121.50-111.00   0.00   52
  7  ω     41.00 106.00   0.50    0.25    --  121.50 -95.00 -30.00  130
  8  ω     41.00 106.00   0.50    0.25    --  121.50 -95.00   0.00  130
  9  ω     46.00  72.00   0.50    0.25    --  121.50 -82.00 -19.62   52
 10  ω     45.00 108.00   0.50    0.25    --  121.50-111.00  90.00  126
 11  ω     41.00 106.00   0.50    0.25    --  121.50 -95.00 150.00  130
 12  ω     46.00 157.00   0.50    0.25    --  121.50 -79.00  42.04  222
 13  ω     46.00 157.00   0.50    0.25    --  121.50 -79.00  42.04  222
 14  ω     47.00  74.00   0.50    0.25    --  121.50 -77.00  90.00   54
 15  ω     47.00 105.00   0.50    0.25    --  121.50 -77.00 150.00  116
 16  ω    123.00 156.00   0.50    0.25    --  121.50 -79.00  62.54   66
 17  ω     92.00 118.00   0.50    0.25    --  121.50 -79.00  62.54   52
 18  ω     76.00 102.00   0.50    0.25    --  121.50 -77.00   0.00   52
 19  ω     47.00  91.00   0.50    0.25    --  121.50 -72.00 103.00   88
 20  ω     59.00  90.00   0.50    0.25    --  121.50 -77.00 -60.00   62
 21  ω    -33.00  74.00   0.50    0.15    --   41.38 -72.00 103.00  214
 22  ω    -75.00  33.00   0.50    0.05    --    0.00 -72.00 103.00  216
 23  ω     47.00 105.00   0.50    0.25    --  121.50 -77.00 -90.00  116
 24  ω     60.00  86.00   0.50    0.25    --  121.50 -77.00-150.00   52
 25  ω     42.00 178.00   0.50    0.25    --  121.50  15.00-150.00  272
 26  ω     89.00 178.00   0.50    0.25    --  121.50  72.00-127.00  178
 27  ω     92.00 178.00   0.50    0.25    --  121.50  61.00 -60.00  172
 28  ω    100.00 127.00   0.50    0.25    --  121.50  45.00   0.00   54
 29  ω     92.00 178.00   0.50    0.25    --  121.50  45.00 -30.00  172
 30  ω     92.00 178.00   0.50    0.25    --  121.50  45.00 -30.00  172
 31  ω     92.00 171.00   0.50    0.25    --  121.50  45.00  90.00  158
 32  ω     84.00 178.00   0.50    0.25    --  121.50  30.00 150.00  188
 33  ω     84.00 178.00   0.50    0.25    --  121.50  30.00 150.00  188
 34  ω     58.00  84.00   0.50    0.25    --  121.50  17.00-104.25   52
 35  ω     92.00 178.00   0.50    0.25    --  121.50  45.00-150.00  172
 36  ω    138.00 178.00   0.50    0.25    --  121.50  45.00-150.00   80
 37  ω     96.00 144.00   0.50    0.25    --  121.50  45.00-180.00   96
 38  ω    142.00 171.00   0.50    0.25    --  121.50  15.00-150.00   58
 39  ω     65.00 178.00   0.50    0.25    --  121.50  22.00 -75.63  226
 40  ω    137.00 163.00   0.50    0.25    --  121.50  15.00 120.00   52
 41  ω     42.00  97.00   0.50    0.25    --  121.50  15.00 120.00  110
 42  ω     -1.00  29.00   0.50    0.15    --   41.38  96.00  -5.07   60
 43  ω    -86.00 -39.00   0.50    0.05    --    0.00 178.00 -60.00   94
 44  ω    -51.00 -21.00   0.50    0.25    -- -100.00  45.00  90.00   60
 45  ω    -27.00  41.00   0.50    0.15    --  -41.38  19.00  60.00  136
 46  ω    121.00 146.00   0.50    0.25    --  121.50 178.00 -60.00   50
 47  ω    -27.00  41.00   0.50    0.15    --  -41.38  19.00  30.00  136
 48  ω    -82.00 -23.00   0.50    0.25    -- -100.00 111.00   0.00  118
 49  ω    -91.00 -24.00   0.50    0.25    -- -100.00  72.00-127.00  134
 50  ω   -175.00 -67.00   0.50    0.25    -- -100.00 -72.00 103.00  216
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0694334000
_diffrn_orient_matrix_UB_12      -0.0670528000
_diffrn_orient_matrix_UB_13      0.0494501000
_diffrn_orient_matrix_UB_21      -0.1681193000
_diffrn_orient_matrix_UB_22      0.0142497000
_diffrn_orient_matrix_UB_23      -0.0834046000
_diffrn_orient_matrix_UB_31      0.0446083000
_diffrn_orient_matrix_UB_32      -0.0505163000
_diffrn_orient_matrix_UB_33      -0.0891641000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3841
_reflns_number_total             3948
_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 1.171.43.125a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.125a 64-bit (release 04-06-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.125a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL  (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.00067(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         3948
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0319
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0419P)²+1.1244P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0851
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O1-H1A = O1-H1B
 0.84 with sigma of 0.02
 Ni1-Cl1 \\sim Ni1-Cl1A \\sim Ni1-Cl1B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(Cl1) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(Cl1) = Uanis(Cl1A) = Uanis(Cl1B)
4. Others
 1*[Sof(Cl1)+Sof(O1)+Sof(H1A)+Sof(H1B)]+1*[Sof(Cl1A)]+1*[Sof(Cl1B)]=1 with esd
 of 0.00001
 Sof(Cl1)=Sof(O1)=Sof(H1A)=Sof(H1B)=FVAR(1)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.55551(3) 0.62477(2) 0.27922(2) 0.02216(10) Uani 1 1 d D . . . .
Cl1 Cl 0.50311(15) 0.66110(8) 0.43976(10) 0.0211(2) Uani 0.501(3) 1 d D U P A 1
Cl1A Cl 0.5272(3) 0.64082(18) 0.4543(2) 0.0211(2) Uani 0.307(3) 1 d D . P A 2
Cl1B Cl 0.5503(4) 0.62816(16) 0.4686(2) 0.0211(2) Uani 0.192(3) 1 d D . P A 3
N1 N 0.89883(17) 0.65966(8) 0.38091(12) 0.0264(3) Uani 1 1 d . . . . .
C1 C 0.78080(19) 0.60988(9) 0.33251(13) 0.0232(3) Uani 1 1 d . . . . .
N2 N 0.86540(16) 0.54622(7) 0.33224(12) 0.0249(3) Uani 1 1 d . . . . .
C2 C 1.0312(2) 0.55620(10) 0.37886(16) 0.0315(3) Uani 1 1 d . . . . .
H2 H 1.105(3) 0.5153(13) 0.388(2) 0.038 Uiso 1 1 d . U . . .
C3 C 1.0520(2) 0.62747(10) 0.40990(17) 0.0328(4) Uani 1 1 d . . . . .
H3 H 1.149(3) 0.6545(13) 0.445(2) 0.039 Uiso 1 1 d . U . . .
C4 C 0.87306(18) 0.73626(9) 0.40026(14) 0.0257(3) Uani 1 1 d . . . . .
C5 C 0.91921(19) 0.76366(9) 0.51107(14) 0.0276(3) Uani 1 1 d . . . . .
F5 F 0.98210(14) 0.71678(6) 0.59773(9) 0.0369(2) Uani 1 1 d . . . . .
C6 C 0.9046(2) 0.83756(10) 0.53419(15) 0.0301(3) Uani 1 1 d . . . . .
H6 H 0.935(3) 0.8528(13) 0.611(2) 0.036 Uiso 1 1 d . U . . .
C7 C 0.8415(2) 0.88518(9) 0.44363(16) 0.0305(3) Uani 1 1 d . . . . .
H7 H 0.830(3) 0.9377(13) 0.4579(19) 0.037 Uiso 1 1 d . U . . .
C8 C 0.7935(2) 0.85889(10) 0.33193(16) 0.0302(3) Uani 1 1 d . . . . .
H8 H 0.748(3) 0.8925(13) 0.268(2) 0.036 Uiso 1 1 d . U . . .
C9 C 0.8097(2) 0.78418(9) 0.31037(15) 0.0283(3) Uani 1 1 d . . . . .
H9 H 0.776(3) 0.7641(12) 0.2272(19) 0.034 Uiso 1 1 d . U . . .
C10 C 0.79566(18) 0.47723(8) 0.28617(13) 0.0233(3) Uani 1 1 d . . . . .
C11 C 0.83071(18) 0.44982(8) 0.18912(13) 0.0234(3) Uani 1 1 d . . . . .
F11 F 0.92845(12) 0.49054(5) 0.14093(8) 0.0307(2) Uani 1 1 d . . . . .
C12 C 0.7672(2) 0.38395(9) 0.13943(14) 0.0261(3) Uani 1 1 d . . . . .
H12 H 0.797(3) 0.3688(11) 0.074(2) 0.031 Uiso 1 1 d . U . . .
C13 C 0.6641(2) 0.34450(9) 0.18893(14) 0.0274(3) Uani 1 1 d . . . . .
H13 H 0.621(3) 0.2979(12) 0.1564(19) 0.033 Uiso 1 1 d . U . . .
C14 C 0.6283(2) 0.37090(9) 0.28706(15) 0.0272(3) Uani 1 1 d . . . . .
H14 H 0.555(3) 0.3444(12) 0.3213(19) 0.033 Uiso 1 1 d . U . . .
C15 C 0.69407(19) 0.43720(9) 0.33611(13) 0.0260(3) Uani 1 1 d . . . . .
H15 H 0.670(3) 0.4584(12) 0.4059(19) 0.031 Uiso 1 1 d . U . . .
C16 C 0.5327(2) 0.60369(10) 0.11038(13) 0.0296(3) Uani 1 1 d . . . . .
H16 H 0.626(3) 0.5900(12) 0.0847(19) 0.035 Uiso 1 1 d . U . . .
C17 C 0.4300(2) 0.55041(9) 0.14330(14) 0.0268(3) Uani 1 1 d . . . . .
H17 H 0.449(3) 0.4954(12) 0.1444(18) 0.032 Uiso 1 1 d . U . . .
C18 C 0.3149(2) 0.58980(10) 0.18066(15) 0.0290(3) Uani 1 1 d . . . . .
H18 H 0.235(3) 0.5704(12) 0.2148(19) 0.035 Uiso 1 1 d . U . . .
C19 C 0.3376(2) 0.66765(10) 0.16300(16) 0.0334(4) Uani 1 1 d . . . . .
H19 H 0.274(3) 0.7058(13) 0.185(2) 0.040 Uiso 1 1 d . U . . .
C20 C 0.4669(2) 0.67580(10) 0.11456(15) 0.0330(4) Uani 1 1 d . . . . .
H20 H 0.502(3) 0.7224(13) 0.094(2) 0.040 Uiso 1 1 d . U . . .
O1 O 0.6594(3) 0.52745(14) 0.5974(2) 0.0307(6) Uani 0.501(3) 1 d D . P A 1
H1A H 0.623(6) 0.563(2) 0.555(4) 0.046 Uiso 0.501(3) 1 d D U P A 1
H1B H 0.597(5) 0.492(2) 0.589(4) 0.046 Uiso 0.501(3) 1 d D U P A 1


_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 2.2131(11) . ?
Ni1 Cl1A 2.2217(19) . ?
Ni1 Cl1B 2.312(3) . ?
Ni1 C1 1.8772(16) . ?
Ni1 C16 2.0422(16) . ?
Ni1 C17 2.1754(15) . ?
Ni1 C18 2.1756(16) . ?
Ni1 C19 2.1553(17) . ?
Ni1 C20 2.1468(17) . ?
N1 C1 1.362(2) . ?
N1 C3 1.388(2) . ?
N1 C4 1.433(2) . ?
C1 N2 1.360(2) . ?
N2 C2 1.388(2) . ?
N2 C10 1.4307(19) . ?
C2 H2 0.96(2) . ?
C2 C3 1.342(2) . ?
C3 H3 0.96(2) . ?
C4 C5 1.388(2) . ?
C4 C9 1.385(2) . ?
C5 F5 1.346(2) . ?
C5 C6 1.379(2) . ?
C6 H6 0.94(2) . ?
C6 C7 1.387(3) . ?
C7 H7 0.98(2) . ?
C7 C8 1.391(3) . ?
C8 H8 0.98(2) . ?
C8 C9 1.391(2) . ?
C9 H9 1.04(2) . ?
C10 C11 1.383(2) . ?
C10 C15 1.388(2) . ?
C11 F11 1.3576(18) . ?
C11 C12 1.379(2) . ?
C12 H12 0.94(2) . ?
C12 C13 1.389(2) . ?
C13 H13 0.96(2) . ?
C13 C14 1.391(2) . ?
C14 H14 0.96(2) . ?
C14 C15 1.389(2) . ?
C15 H15 1.00(2) . ?
C16 H16 0.96(2) . ?
C16 C17 1.430(2) . ?
C16 C20 1.427(3) . ?
C17 H17 1.01(2) . ?
C17 C18 1.385(2) . ?
C18 H18 0.95(2) . ?
C18 C19 1.446(3) . ?
C19 H19 0.96(2) . ?
C19 C20 1.391(3) . ?
C20 H20 0.95(2) . ?
O1 H1A 0.83(2) . ?
O1 H1B 0.82(2) . ?

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
C1 Ni1 Cl1 99.77(6) . . ?
C1 Ni1 Cl1A 93.06(9) . . ?
C1 Ni1 Cl1B 87.26(9) . . ?
C1 Ni1 C16 97.59(7) . . ?
C1 Ni1 C17 115.06(7) . . ?
C1 Ni1 C18 151.28(7) . . ?
C1 Ni1 C19 154.42(7) . . ?
C1 Ni1 C20 117.07(7) . . ?
C16 Ni1 Cl1 162.17(6) . . ?
C16 Ni1 Cl1A 168.26(8) . . ?
C16 Ni1 Cl1B 168.78(9) . . ?
C16 Ni1 C17 39.49(7) . . ?
C16 Ni1 C18 64.66(7) . . ?
C16 Ni1 C19 64.98(7) . . ?
C16 Ni1 C20 39.73(7) . . ?
C17 Ni1 Cl1 132.59(6) . . ?
C17 Ni1 Cl1A 130.44(7) . . ?
C17 Ni1 Cl1B 129.32(8) . . ?
C17 Ni1 C18 37.12(6) . . ?
C18 Ni1 Cl1 100.76(6) . . ?
C18 Ni1 Cl1A 103.61(7) . . ?
C18 Ni1 Cl1B 106.71(8) . . ?
C19 Ni1 Cl1 97.28(6) . . ?
C19 Ni1 Cl1A 106.44(10) . . ?
C19 Ni1 Cl1B 113.46(10) . . ?
C19 Ni1 C17 64.08(6) . . ?
C19 Ni1 C18 38.99(7) . . ?
C20 Ni1 Cl1 126.03(7) . . ?
C20 Ni1 Cl1A 137.14(11) . . ?
C20 Ni1 Cl1B 144.93(10) . . ?
C20 Ni1 C17 65.22(6) . . ?
C20 Ni1 C18 64.41(7) . . ?
C20 Ni1 C19 37.72(7) . . ?
C1 N1 C3 111.70(14) . . ?
C1 N1 C4 125.60(14) . . ?
C3 N1 C4 122.69(14) . . ?
N1 C1 Ni1 128.70(12) . . ?
N2 C1 Ni1 128.06(11) . . ?
N2 C1 N1 103.24(13) . . ?
C1 N2 C2 111.90(14) . . ?
C1 N2 C10 125.04(13) . . ?
C2 N2 C10 123.02(14) . . ?
N2 C2 H2 120.7(14) . . ?
C3 C2 N2 106.46(15) . . ?
C3 C2 H2 132.7(14) . . ?
N1 C3 H3 122.7(14) . . ?
C2 C3 N1 106.70(15) . . ?
C2 C3 H3 130.6(14) . . ?
C5 C4 N1 119.23(15) . . ?
C9 C4 N1 121.40(15) . . ?
C9 C4 C5 119.30(15) . . ?
F5 C5 C4 118.85(15) . . ?
F5 C5 C6 119.41(15) . . ?
C6 C5 C4 121.74(16) . . ?
C5 C6 H6 118.2(14) . . ?
C5 C6 C7 118.58(16) . . ?
C7 C6 H6 123.2(14) . . ?
C6 C7 H7 120.1(14) . . ?
C6 C7 C8 120.69(16) . . ?
C8 C7 H7 119.2(14) . . ?
C7 C8 H8 120.6(14) . . ?
C9 C8 C7 119.85(17) . . ?
C9 C8 H8 119.5(14) . . ?
C4 C9 C8 119.84(16) . . ?
C4 C9 H9 119.7(12) . . ?
C8 C9 H9 120.5(12) . . ?
C11 C10 N2 118.91(14) . . ?
C11 C10 C15 119.24(14) . . ?
C15 C10 N2 121.86(14) . . ?
F11 C11 C10 118.09(14) . . ?
F11 C11 C12 119.69(14) . . ?
C12 C11 C10 122.20(15) . . ?
C11 C12 H12 117.4(13) . . ?
C11 C12 C13 118.37(15) . . ?
C13 C12 H12 124.2(13) . . ?
C12 C13 H13 119.5(13) . . ?
C12 C13 C14 120.28(15) . . ?
C14 C13 H13 120.2(13) . . ?
C13 C14 H14 120.9(13) . . ?
C15 C14 C13 120.48(15) . . ?
C15 C14 H14 118.6(13) . . ?
C10 C15 C14 119.43(15) . . ?
C10 C15 H15 117.8(12) . . ?
C14 C15 H15 122.8(12) . . ?
Ni1 C16 H16 120.6(14) . . ?
C17 C16 Ni1 75.28(9) . . ?
C17 C16 H16 122.6(14) . . ?
C20 C16 Ni1 74.09(10) . . ?
C20 C16 H16 128.0(14) . . ?
C20 C16 C17 109.23(15) . . ?
Ni1 C17 H17 123.7(12) . . ?
C16 C17 Ni1 65.22(9) . . ?
C16 C17 H17 124.0(12) . . ?
C18 C17 Ni1 71.45(9) . . ?
C18 C17 C16 106.67(14) . . ?
C18 C17 H17 129.1(12) . . ?
Ni1 C18 H18 123.1(14) . . ?
C17 C18 Ni1 71.43(9) . . ?
C17 C18 H18 127.2(14) . . ?
C17 C18 C19 108.52(15) . . ?
C19 C18 Ni1 69.75(9) . . ?
C19 C18 H18 124.2(14) . . ?
Ni1 C19 H19 122.0(14) . . ?
C18 C19 Ni1 71.26(9) . . ?
C18 C19 H19 123.6(14) . . ?
C20 C19 Ni1 70.81(10) . . ?
C20 C19 C18 108.62(15) . . ?
C20 C19 H19 127.8(14) . . ?
Ni1 C20 H20 124.8(15) . . ?
C16 C20 Ni1 66.18(9) . . ?
C16 C20 H20 130.0(14) . . ?
C19 C20 Ni1 71.47(10) . . ?
C19 C20 C16 106.43(15) . . ?
C19 C20 H20 123.5(14) . . ?
H1A O1 H1B 114(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1A Cl1 0.83(2) 2.32(2) 3.150(3) 175(5) . yes
O1 H1B Cl1 0.82(2) 2.89(3) 3.665(3) 157(5) 3_666 yes

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 C1 N2 C2 -179.95(12) . . . . ?
Ni1 C1 N2 C10 2.2(2) . . . . ?
Ni1 C16 C17 C18 59.74(12) . . . . ?
Ni1 C16 C20 C19 -60.50(12) . . . . ?
Ni1 C17 C18 C19 60.16(11) . . . . ?
Ni1 C18 C19 C20 61.28(12) . . . . ?
Ni1 C19 C20 C16 57.11(11) . . . . ?
Cl1 Ni1 C1 N1 -60.27(15) . . . . ?
Cl1 Ni1 C1 N2 119.50(14) . . . . ?
Cl1A Ni1 C1 N1 -69.35(16) . . . . ?
Cl1A Ni1 C1 N2 110.41(16) . . . . ?
Cl1B Ni1 C1 N1 -74.57(16) . . . . ?
Cl1B Ni1 C1 N2 105.19(16) . . . . ?
N1 C1 N2 C2 -0.14(18) . . . . ?
N1 C1 N2 C10 -177.96(14) . . . . ?
N1 C4 C5 F5 -2.2(2) . . . . ?
N1 C4 C5 C6 176.81(15) . . . . ?
N1 C4 C9 C8 -176.95(15) . . . . ?
C1 N1 C3 C2 0.4(2) . . . . ?
C1 N1 C4 C5 120.02(17) . . . . ?
C1 N1 C4 C9 -62.8(2) . . . . ?
C1 N2 C2 C3 0.4(2) . . . . ?
C1 N2 C10 C11 111.66(18) . . . . ?
C1 N2 C10 C15 -68.3(2) . . . . ?
N2 C2 C3 N1 -0.4(2) . . . . ?
N2 C10 C11 F11 -0.9(2) . . . . ?
N2 C10 C11 C12 -179.60(14) . . . . ?
N2 C10 C15 C14 179.33(14) . . . . ?
C2 N2 C10 C11 -65.9(2) . . . . ?
C2 N2 C10 C15 114.08(18) . . . . ?
C3 N1 C1 Ni1 179.67(13) . . . . ?
C3 N1 C1 N2 -0.14(18) . . . . ?
C3 N1 C4 C5 -60.4(2) . . . . ?
C3 N1 C4 C9 116.76(19) . . . . ?
C4 N1 C1 Ni1 -0.7(2) . . . . ?
C4 N1 C1 N2 179.50(14) . . . . ?
C4 N1 C3 C2 -179.29(16) . . . . ?
C4 C5 C6 C7 0.2(2) . . . . ?
C5 C4 C9 C8 0.2(2) . . . . ?
C5 C6 C7 C8 0.2(3) . . . . ?
F5 C5 C6 C7 179.18(15) . . . . ?
C6 C7 C8 C9 -0.4(3) . . . . ?
C7 C8 C9 C4 0.2(2) . . . . ?
C9 C4 C5 F5 -179.37(14) . . . . ?
C9 C4 C5 C6 -0.4(2) . . . . ?
C10 N2 C2 C3 178.23(16) . . . . ?
C10 C11 C12 C13 0.3(2) . . . . ?
C11 C10 C15 C14 -0.7(2) . . . . ?
C11 C12 C13 C14 -0.8(2) . . . . ?
F11 C11 C12 C13 -178.29(14) . . . . ?
C12 C13 C14 C15 0.5(2) . . . . ?
C13 C14 C15 C10 0.2(2) . . . . ?
C15 C10 C11 F11 179.05(13) . . . . ?
C15 C10 C11 C12 0.4(2) . . . . ?
C16 Ni1 C1 N1 115.60(15) . . . . ?
C16 Ni1 C1 N2 -64.64(15) . . . . ?
C16 C17 C18 Ni1 -55.81(11) . . . . ?
C16 C17 C18 C19 4.34(18) . . . . ?
C17 Ni1 C1 N1 152.74(13) . . . . ?
C17 Ni1 C1 N2 -27.49(16) . . . . ?
C17 C16 C20 Ni1 67.71(11) . . . . ?
C17 C16 C20 C19 7.21(19) . . . . ?
C17 C18 C19 Ni1 -61.21(12) . . . . ?
C17 C18 C19 C20 0.06(19) . . . . ?
C18 Ni1 C1 N1 164.65(13) . . . . ?
C18 Ni1 C1 N2 -15.6(2) . . . . ?
C18 C19 C20 Ni1 -61.56(12) . . . . ?
C18 C19 C20 C16 -4.45(19) . . . . ?
C19 Ni1 C1 N1 70.8(2) . . . . ?
C19 Ni1 C1 N2 -109.40(18) . . . . ?
C20 Ni1 C1 N1 79.04(16) . . . . ?
C20 Ni1 C1 N2 -101.19(15) . . . . ?
C20 C16 C17 Ni1 -66.93(11) . . . . ?
C20 C16 C17 C18 -7.20(18) . . . . ?

_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 1.175
_oxdiff_exptl_absorpt_empirical_full_min 0.913
