# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_l12014
_database_code_depnum_ccdc_archive 'CCDC 2076279'
loop_
_audit_author_name
_audit_author_address
'Liviu Mirica'
;University of Illinois at Urbana Champaign
United States of America
;
_audit_update_record             
;
2021-04-08 deposited with the CCDC.	2021-06-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H20 Cl2 N4 Ni, F6 P'
_chemical_formula_sum            'C16 H20 Cl2 F6 N4 Ni P'
_chemical_formula_weight         542.94

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.9385(3)
_cell_length_b                   12.1873(3)
_cell_length_c                   12.9860(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.5138(15)
_cell_angle_gamma                90
_cell_volume                     2006.50(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5029
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      26.85

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.797
_exptl_crystal_F_000             1100
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.302
_exptl_crystal_size_mid          0.271
_exptl_crystal_size_min          0.101
_exptl_absorpt_coefficient_mu    1.379
_shelx_estimated_absorpt_T_min   0.681
_shelx_estimated_absorpt_T_max   0.873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6738
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_process_details   'sadabs v2012/1'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24160
_diffrn_reflns_av_unetI/netI     0.0546
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.314
_diffrn_reflns_theta_max         27.541
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4618
_reflns_number_gt                3449
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
  
All  H atoms were positioned geometrically and refined using a 
riding model with C---H = 0.95--0.99 Å and with Uiso(H) 
= 1.2 (1.5 for methyl groups) times Ueq(C). 
  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0511P)²+2.8824P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4618
_refine_ls_number_parameters     399
_refine_ls_number_restraints     590
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1129
_refine_ls_wR_factor_gt          0.1002
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.145
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.17575(3) 0.32597(3) 0.30829(3) 0.01478(12) Uani 1 1 d D . . . .
Cl1 Cl 0.06756(6) 0.23017(7) 0.38588(6) 0.02153(19) Uani 1 1 d . . . . .
Cl2 Cl 0.17719(8) 0.20009(7) 0.18840(8) 0.0351(2) Uani 1 1 d . . . . .
N1 N 0.2688(2) 0.4114(2) 0.2449(2) 0.0168(6) Uani 1 1 d . . . . .
N3 N 0.0577(2) 0.4320(3) 0.2180(2) 0.0253(7) Uani 1 1 d . . . . .
N4 N 0.3226(2) 0.2790(3) 0.4092(3) 0.0370(9) Uani 1 1 d D . . . .
C1 C 0.2285(3) 0.4878(3) 0.1740(3) 0.0226(7) Uani 1 1 d . . . . .
C2 C 0.2947(3) 0.5482(3) 0.1250(3) 0.0303(9) Uani 1 1 d . . . . .
H2 H 0.2669 0.6025 0.0745 0.036 Uiso 1 1 calc R U . . .
C3 C 0.4011(3) 0.5290(3) 0.1500(3) 0.0311(9) Uani 1 1 d . . . . .
H3 H 0.4474 0.5697 0.1162 0.037 Uiso 1 1 calc R U . . .
C4 C 0.4416(3) 0.4508(3) 0.2239(3) 0.0259(8) Uani 1 1 d . . . . .
H4 H 0.5154 0.4379 0.2424 0.031 Uiso 1 1 calc R U . . .
C5 C 0.3722(3) 0.3917(3) 0.2704(2) 0.0186(7) Uani 1 1 d . . . . .
C6 C 0.4034(3) 0.2981(3) 0.3459(3) 0.0272(8) Uani 1 1 d . . . . .
H6A H 0.4126 0.2307 0.3061 0.033 Uiso 1 1 calc R U . . .
H6B H 0.4716 0.3152 0.3929 0.033 Uiso 1 1 calc R U . . .
C14 C 0.1119(3) 0.5024(4) 0.1544(4) 0.0426(11) Uani 1 1 d . . . . .
H14A H 0.0963 0.5799 0.1683 0.051 Uiso 1 1 calc R U . . .
H14B H 0.0829 0.4876 0.0792 0.051 Uiso 1 1 calc R U . . .
C15 C -0.0294(3) 0.3756(5) 0.1482(4) 0.0580(15) Uani 1 1 d . . . . .
H15A H -0.0031 0.3411 0.0903 0.087 Uiso 1 1 calc R U . . .
H15B H -0.0845 0.4289 0.1197 0.087 Uiso 1 1 calc R U . . .
H15C H -0.0588 0.3193 0.1879 0.087 Uiso 1 1 calc R U . . .
C7 C 0.3320(8) 0.3139(11) 0.5058(7) 0.026(2) Uani 0.390(9) 1 d D U P A 1
H7A H 0.4071 0.3254 0.5386 0.032 Uiso 0.390(9) 1 calc R U P A 1
H7B H 0.3011 0.2605 0.5486 0.032 Uiso 0.390(9) 1 calc R U P A 1
C7' C 0.3380(5) 0.3733(7) 0.4970(4) 0.0222(13) Uani 0.610(9) 1 d D U P A 2
H7'1 H 0.3524 0.3381 0.5671 0.027 Uiso 0.610(9) 1 calc R U P A 2
H7'2 H 0.4010 0.4170 0.4909 0.027 Uiso 0.610(9) 1 calc R U P A 2
N2 N 0.1960(10) 0.4320(11) 0.4144(10) 0.013(2) Uani 0.390(9) 1 d D U P A 1
C8 C 0.2734(9) 0.4192(9) 0.4970(8) 0.019(2) Uani 0.390(9) 1 d D U P A 1
C9 C 0.2846(10) 0.4950(10) 0.5768(8) 0.028(2) Uani 0.390(9) 1 d D U P A 1
H9 H 0.3379 0.4866 0.6381 0.033 Uiso 0.390(9) 1 calc R U P A 1
C10 C 0.2180(13) 0.5820(11) 0.5663(9) 0.031(3) Uani 0.390(9) 1 d D U P A 1
H10 H 0.2265 0.6354 0.6206 0.037 Uiso 0.390(9) 1 calc R U P A 1
C11 C 0.1381(11) 0.5953(8) 0.4790(9) 0.030(2) Uani 0.390(9) 1 d D U P A 1
H11 H 0.0903 0.6551 0.4733 0.036 Uiso 0.390(9) 1 calc R U P A 1
C12 C 0.1309(10) 0.5173(10) 0.4003(9) 0.0239(14) Uani 0.390(9) 1 d D U P A 1
N2' N 0.1671(7) 0.4403(7) 0.4076(6) 0.0167(18) Uani 0.610(9) 1 d D U P A 2
C8' C 0.2455(6) 0.4508(7) 0.4915(6) 0.0222(13) Uani 0.610(9) 1 d D U P A 2
C9' C 0.2414(8) 0.5327(7) 0.5664(5) 0.032(2) Uani 0.610(9) 1 d D U P A 2
H9' H 0.2965 0.5407 0.6264 0.038 Uiso 0.610(9) 1 calc R U P A 2
C10' C 0.1563(9) 0.5999(5) 0.5506(6) 0.0373(19) Uani 0.610(9) 1 d D U P A 2
H10' H 0.1521 0.6563 0.6001 0.045 Uiso 0.610(9) 1 calc R U P A 2
C11' C 0.0744(8) 0.5878(6) 0.4627(5) 0.0376(19) Uani 0.610(9) 1 d D U P A 2
H11' H 0.0142 0.6343 0.4527 0.045 Uiso 0.610(9) 1 calc R U P A 2
C12' C 0.0836(6) 0.5068(6) 0.3915(5) 0.0239(14) Uani 0.610(9) 1 d D U P A 2
C13 C 0.0475(11) 0.5194(11) 0.3034(9) 0.035(3) Uani 0.390(9) 1 d . U P A 1
H13A H 0.0472 0.5931 0.2713 0.042 Uiso 0.390(9) 1 calc R U P A 1
H13B H -0.0216 0.5092 0.3238 0.042 Uiso 0.390(9) 1 calc R U P A 1
C16 C 0.3267(10) 0.1408(10) 0.4047(12) 0.039(3) Uani 0.390(9) 1 d . . P A 1
H16A H 0.2644 0.1105 0.4268 0.058 Uiso 0.390(9) 1 calc R U P A 1
H16B H 0.3905 0.1145 0.4521 0.058 Uiso 0.390(9) 1 calc R U P A 1
H16C H 0.3275 0.1171 0.3328 0.058 Uiso 0.390(9) 1 calc R U P A 1
C13' C 0.0011(6) 0.4787(7) 0.2956(6) 0.0328(19) Uani 0.610(9) 1 d . U P A 2
H13C H -0.0496 0.4247 0.3136 0.039 Uiso 0.610(9) 1 calc R U P A 2
H13D H -0.0382 0.5453 0.2670 0.039 Uiso 0.610(9) 1 calc R U P A 2
C16' C 0.3227(6) 0.1766(7) 0.4626(7) 0.040(2) Uani 0.610(9) 1 d . . P A 2
H16D H 0.2724 0.1798 0.5098 0.060 Uiso 0.610(9) 1 calc R U P A 2
H16E H 0.3936 0.1620 0.5036 0.060 Uiso 0.610(9) 1 calc R U P A 2
H16F H 0.3023 0.1178 0.4111 0.060 Uiso 0.610(9) 1 calc R U P A 2
P1 P 0.33591(7) 0.76429(8) 0.35824(7) 0.0256(2) Uani 1 1 d D U . . .
F1 F 0.3106(3) 0.8883(2) 0.3202(3) 0.0458(9) Uani 0.828(5) 1 d D U P B 1
F2 F 0.4062(3) 0.7519(3) 0.2702(3) 0.0472(10) Uani 0.828(5) 1 d D U P B 1
F3 F 0.3589(4) 0.6410(3) 0.3887(3) 0.0616(12) Uani 0.828(5) 1 d D U P B 1
F4 F 0.2624(3) 0.7791(3) 0.4407(3) 0.0472(11) Uani 0.828(5) 1 d D U P B 1
F5 F 0.4345(2) 0.8071(3) 0.4393(3) 0.0587(12) Uani 0.828(5) 1 d D U P B 1
F6 F 0.2347(2) 0.7263(3) 0.2723(3) 0.0528(11) Uani 0.828(5) 1 d D U P B 1
F1' F 0.3705(11) 0.8896(6) 0.3757(12) 0.056(4) Uani 0.172(5) 1 d D U P B 2
F2' F 0.4453(7) 0.7347(10) 0.3276(12) 0.042(4) Uani 0.172(5) 1 d D U P B 2
F3' F 0.3029(11) 0.6389(6) 0.3530(11) 0.039(4) Uani 0.172(5) 1 d D U P B 2
F4' F 0.2326(7) 0.7917(12) 0.4020(11) 0.035(4) Uani 0.172(5) 1 d D U P B 2
F5' F 0.2814(12) 0.7838(12) 0.2426(6) 0.059(4) Uani 0.172(5) 1 d D U P B 2
F6' F 0.3938(10) 0.7450(11) 0.4802(6) 0.046(4) Uani 0.172(5) 1 d D U P B 2


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 N2 1.869(9) . ?
Ni1 N1 1.900(3) . ?
Ni1 N2' 1.916(6) . ?
Ni1 N4 2.159(3) . ?
Ni1 N3 2.159(3) . ?
Ni1 Cl2 2.1885(9) . ?
Ni1 Cl1 2.2138(9) . ?
N1 C5 1.333(4) . ?
N1 C1 1.340(4) . ?
N3 C14 1.463(5) . ?
N3 C15 1.468(5) . ?
N3 C13' 1.473(8) . ?
N3 C13 1.562(12) . ?
N4 C7 1.307(10) . ?
N4 C16' 1.427(8) . ?
N4 C6 1.471(5) . ?
N4 C7' 1.604(8) . ?
N4 C16 1.686(13) . ?
C1 C2 1.377(5) . ?
C1 C14 1.490(5) . ?
C2 C3 1.371(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.505(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C7 C8 1.484(14) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7' C8' 1.515(9) . ?
C7' H7'1 0.9900 . ?
C7' H7'2 0.9900 . ?
N2 C8 1.323(11) . ?
N2 C12 1.327(11) . ?
C8 C9 1.374(12) . ?
C9 C10 1.355(15) . ?
C9 H9 0.9500 . ?
C10 C11 1.383(15) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(11) . ?
C11 H11 0.9500 . ?
C12 C13 1.486(14) . ?
N2' C12' 1.333(8) . ?
N2' C8' 1.338(8) . ?
C8' C9' 1.402(10) . ?
C9' C10' 1.354(11) . ?
C9' H9' 0.9500 . ?
C10' C11' 1.402(11) . ?
C10' H10' 0.9500 . ?
C11' C12' 1.375(8) . ?
C11' H11' 0.9500 . ?
C12' C13' 1.509(9) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C13' H13C 0.9900 . ?
C13' H13D 0.9900 . ?
C16' H16D 0.9800 . ?
C16' H16E 0.9800 . ?
C16' H16F 0.9800 . ?
P1 F5' 1.545(6) . ?
P1 F3 1.568(3) . ?
P1 F5 1.572(3) . ?
P1 F4 1.578(3) . ?
P1 F3' 1.585(6) . ?
P1 F2' 1.587(6) . ?
P1 F4' 1.589(6) . ?
P1 F1' 1.594(6) . ?
P1 F1 1.604(3) . ?
P1 F2 1.604(3) . ?
P1 F6 1.610(3) . ?
P1 F6' 1.629(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Ni1 N1 86.1(5) . . ?
N1 Ni1 N2' 91.1(4) . . ?
N2 Ni1 N4 76.1(3) . . ?
N1 Ni1 N4 81.43(11) . . ?
N2' Ni1 N4 87.0(2) . . ?
N2 Ni1 N3 88.1(4) . . ?
N1 Ni1 N3 82.97(12) . . ?
N2' Ni1 N3 78.5(2) . . ?
N4 Ni1 N3 158.40(13) . . ?
N2 Ni1 Cl2 171.6(4) . . ?
N1 Ni1 Cl2 88.85(8) . . ?
N2' Ni1 Cl2 176.4(2) . . ?
N4 Ni1 Cl2 96.56(11) . . ?
N3 Ni1 Cl2 97.97(8) . . ?
N2 Ni1 Cl1 92.2(5) . . ?
N1 Ni1 Cl1 178.28(8) . . ?
N2' Ni1 Cl1 87.2(4) . . ?
N4 Ni1 Cl1 98.26(9) . . ?
N3 Ni1 Cl1 96.88(9) . . ?
Cl2 Ni1 Cl1 92.87(3) . . ?
C5 N1 C1 121.9(3) . . ?
C5 N1 Ni1 119.0(2) . . ?
C1 N1 Ni1 119.0(2) . . ?
C14 N3 C15 108.7(3) . . ?
C14 N3 C13' 121.3(5) . . ?
C15 N3 C13' 100.2(4) . . ?
C14 N3 C13 96.8(7) . . ?
C15 N3 C13 126.5(6) . . ?
C14 N3 Ni1 106.9(2) . . ?
C15 N3 Ni1 115.3(3) . . ?
C13' N3 Ni1 104.7(3) . . ?
C13 N3 Ni1 100.0(4) . . ?
C7 N4 C6 123.0(6) . . ?
C16' N4 C6 118.6(4) . . ?
C16' N4 C7' 107.1(5) . . ?
C6 N4 C7' 106.4(4) . . ?
C7 N4 C16 111.1(7) . . ?
C6 N4 C16 96.3(6) . . ?
C7 N4 Ni1 113.4(5) . . ?
C16' N4 Ni1 116.2(4) . . ?
C6 N4 Ni1 104.8(2) . . ?
C7' N4 Ni1 102.1(3) . . ?
C16 N4 Ni1 105.9(4) . . ?
N1 C1 C2 119.8(3) . . ?
N1 C1 C14 116.2(3) . . ?
C2 C1 C14 124.0(3) . . ?
C3 C2 C1 119.1(3) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 120.5(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 118.3(3) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
N1 C5 C4 120.3(3) . . ?
N1 C5 C6 115.0(3) . . ?
C4 C5 C6 124.5(3) . . ?
N4 C6 C5 110.9(3) . . ?
N4 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
N4 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
N3 C14 C1 114.6(3) . . ?
N3 C14 H14A 108.6 . . ?
C1 C14 H14A 108.6 . . ?
N3 C14 H14B 108.6 . . ?
C1 C14 H14B 108.6 . . ?
H14A C14 H14B 107.6 . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N4 C7 C8 105.1(7) . . ?
N4 C7 H7A 110.7 . . ?
C8 C7 H7A 110.7 . . ?
N4 C7 H7B 110.7 . . ?
C8 C7 H7B 110.7 . . ?
H7A C7 H7B 108.8 . . ?
C8' C7' N4 115.4(5) . . ?
C8' C7' H7'1 108.4 . . ?
N4 C7' H7'1 108.4 . . ?
C8' C7' H7'2 108.4 . . ?
N4 C7' H7'2 108.4 . . ?
H7'1 C7' H7'2 107.5 . . ?
C8 N2 C12 124.1(9) . . ?
C8 N2 Ni1 119.2(8) . . ?
C12 N2 Ni1 116.7(8) . . ?
N2 C8 C9 118.7(11) . . ?
N2 C8 C7 117.2(9) . . ?
C9 C8 C7 123.3(9) . . ?
C10 C9 C8 118.8(11) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C9 C10 C11 122.0(10) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C10 C11 C12 117.0(10) . . ?
C10 C11 H11 121.5 . . ?
C12 C11 H11 121.5 . . ?
N2 C12 C11 119.2(10) . . ?
N2 C12 C13 117.6(9) . . ?
C11 C12 C13 123.0(10) . . ?
C12' N2' C8' 121.8(6) . . ?
C12' N2' Ni1 119.4(5) . . ?
C8' N2' Ni1 118.8(5) . . ?
N2' C8' C9' 120.4(7) . . ?
N2' C8' C7' 116.2(6) . . ?
C9' C8' C7' 123.3(6) . . ?
C10' C9' C8' 117.9(7) . . ?
C10' C9' H9' 121.1 . . ?
C8' C9' H9' 121.1 . . ?
C9' C10' C11' 121.3(6) . . ?
C9' C10' H10' 119.4 . . ?
C11' C10' H10' 119.4 . . ?
C12' C11' C10' 118.0(7) . . ?
C12' C11' H11' 121.0 . . ?
C10' C11' H11' 121.0 . . ?
N2' C12' C11' 120.5(6) . . ?
N2' C12' C13' 114.1(6) . . ?
C11' C12' C13' 125.2(6) . . ?
C12 C13 N3 116.1(8) . . ?
C12 C13 H13A 108.3 . . ?
N3 C13 H13A 108.3 . . ?
C12 C13 H13B 108.3 . . ?
N3 C13 H13B 108.3 . . ?
H13A C13 H13B 107.4 . . ?
N4 C16 H16A 109.5 . . ?
N4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C13' C12' 106.6(5) . . ?
N3 C13' H13C 110.4 . . ?
C12' C13' H13C 110.4 . . ?
N3 C13' H13D 110.4 . . ?
C12' C13' H13D 110.4 . . ?
H13C C13' H13D 108.6 . . ?
N4 C16' H16D 109.5 . . ?
N4 C16' H16E 109.5 . . ?
H16D C16' H16E 109.5 . . ?
N4 C16' H16F 109.5 . . ?
H16D C16' H16F 109.5 . . ?
H16E C16' H16F 109.5 . . ?
F3 P1 F5 93.5(2) . . ?
F3 P1 F4 92.7(2) . . ?
F5 P1 F4 91.5(2) . . ?
F5' P1 F3' 92.3(6) . . ?
F5' P1 F2' 92.8(6) . . ?
F3' P1 F2' 90.9(5) . . ?
F5' P1 F4' 93.5(6) . . ?
F3' P1 F4' 88.8(6) . . ?
F2' P1 F4' 173.7(6) . . ?
F5' P1 F1' 92.9(6) . . ?
F3' P1 F1' 174.4(6) . . ?
F2' P1 F1' 90.8(5) . . ?
F4' P1 F1' 88.8(6) . . ?
F3 P1 F1 176.8(2) . . ?
F5 P1 F1 88.93(18) . . ?
F4 P1 F1 89.30(19) . . ?
F3 P1 F2 89.10(19) . . ?
F5 P1 F2 90.49(19) . . ?
F4 P1 F2 177.2(2) . . ?
F1 P1 F2 88.78(18) . . ?
F3 P1 F6 89.2(2) . . ?
F5 P1 F6 177.1(2) . . ?
F4 P1 F6 89.23(19) . . ?
F1 P1 F6 88.30(18) . . ?
F2 P1 F6 88.68(18) . . ?
F5' P1 F6' 179.4(6) . . ?
F3' P1 F6' 88.3(5) . . ?
F2' P1 F6' 87.2(5) . . ?
F4' P1 F6' 86.5(5) . . ?
F1' P1 F6' 86.5(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2_a Ni1 N1 C5 89.3(4) . . . . ?
N2' Ni1 N1 C5 99.5(3) . . . . ?
N4 Ni1 N1 C5 12.8(2) . . . . ?
N3 Ni1 N1 C5 177.8(2) . . . . ?
Cl2 Ni1 N1 C5 -84.0(2) . . . . ?
N2 Ni1 N1 C1 -92.4(4) . . . . ?
N2' Ni1 N1 C1 -82.2(3) . . . . ?
N4 Ni1 N1 C1 -168.9(3) . . . . ?
N3 Ni1 N1 C1 -3.9(2) . . . . ?
Cl2 Ni1 N1 C1 94.3(2) . . . . ?
C5 N1 C1 C2 0.2(5) . . . . ?
Ni1 N1 C1 C2 -178.0(2) . . . . ?
C5 N1 C1 C14 -179.1(3) . . . . ?
Ni1 N1 C1 C14 2.7(4) . . . . ?
N1 C1 C2 C3 -0.1(5) . . . . ?
C14 C1 C2 C3 179.1(4) . . . . ?
C1 C2 C3 C4 -0.5(5) . . . . ?
C2 C3 C4 C5 1.0(5) . . . . ?
C1 N1 C5 C4 0.3(5) . . . . ?
Ni1 N1 C5 C4 178.6(2) . . . . ?
C1 N1 C5 C6 -176.1(3) . . . . ?
Ni1 N1 C5 C6 2.2(4) . . . . ?
C3 C4 C5 N1 -0.9(5) . . . . ?
C3 C4 C5 C6 175.1(3) . . . . ?
C7 N4 C6 C5 -100.7(7) . . . . ?
C16' N4 C6 C5 162.4(5) . . . . ?
C7' N4 C6 C5 -77.0(4) . . . . ?
C16 N4 C6 C5 139.0(5) . . . . ?
Ni1 N4 C6 C5 30.7(4) . . . . ?
N1 C5 C6 N4 -24.2(4) . . . . ?
C4 C5 C6 N4 159.6(3) . . . . ?
C15 N3 C14 C1 -129.0(4) . . . . ?
C13' N3 C14 C1 115.8(5) . . . . ?
C13 N3 C14 C1 98.7(6) . . . . ?
Ni1 N3 C14 C1 -3.9(4) . . . . ?
N1 C1 C14 N3 1.3(5) . . . . ?
C2 C1 C14 N3 -177.9(3) . . . . ?
C16' N4 C7 C8 -146.1(10) . . . . ?
C6 N4 C7 C8 96.2(9) . . . . ?
C7' N4 C7 C8 38.2(9) . . . . ?
C16 N4 C7 C8 -150.8(9) . . . . ?
Ni1 N4 C7 C8 -31.7(11) . . . . ?
C7 N4 C7' C8' -110.7(14) . . . . ?
C16' N4 C7' C8' -115.1(6) . . . . ?
C6 N4 C7' C8' 117.2(5) . . . . ?
C16 N4 C7' C8' -123.3(9) . . . . ?
Ni1 N4 C7' C8' 7.5(6) . . . . ?
N1 Ni1 N2 C8 -90.4(12) . . . . ?
N2' Ni1 N2 C8 154(5) . . . . ?
N4 Ni1 N2 C8 -8.3(11) . . . . ?
N3 Ni1 N2 C8 -173.5(13) . . . . ?
Cl1 Ni1 N2 C8 89.7(12) . . . . ?
N1 Ni1 N2 C12 88.8(12) . . . . ?
N2' Ni1 N2 C12 -27(3) . . . . ?
N4 Ni1 N2 C12 170.9(13) . . . . ?
N3 Ni1 N2 C12 5.7(12) . . . . ?
Cl1 Ni1 N2 C12 -91.1(12) . . . . ?
C12 N2 C8 C9 4(2) . . . . ?
Ni1 N2 C8 C9 -177.1(10) . . . . ?
C12 N2 C8 C7 174.0(14) . . . . ?
Ni1 N2 C8 C7 -6.8(18) . . . . ?
N4 C7 C8 N2 26.4(16) . . . . ?
N4 C7 C8 C9 -163.9(10) . . . . ?
N2 C8 C9 C10 -2.1(18) . . . . ?
C7 C8 C9 C10 -171.7(12) . . . . ?
C8 C9 C10 C11 1.4(18) . . . . ?
C9 C10 C11 C12 -2.1(18) . . . . ?
C8 N2 C12 C11 -5(2) . . . . ?
Ni1 N2 C12 C11 176.2(10) . . . . ?
C8 N2 C12 C13 -179.7(14) . . . . ?
Ni1 N2 C12 C13 1.2(18) . . . . ?
C10 C11 C12 N2 3.6(18) . . . . ?
C10 C11 C12 C13 178.4(12) . . . . ?
C12' N2' C8' C9' 0.6(14) . . . . ?
Ni1 N2' C8' C9' -179.2(7) . . . . ?
C12' N2' C8' C7' -177.1(9) . . . . ?
Ni1 N2' C8' C7' 3.1(11) . . . . ?
N4 C7' C8' N2' -7.6(10) . . . . ?
N4 C7' C8' C9' 174.8(7) . . . . ?
N2' C8' C9' C10' -0.2(12) . . . . ?
C7' C8' C9' C10' 177.3(7) . . . . ?
C8' C9' C10' C11' 0.5(12) . . . . ?
C9' C10' C11' C12' -1.2(12) . . . . ?
C8' N2' C12' C11' -1.4(15) . . . . ?
Ni1 N2' C12' C11' 178.5(7) . . . . ?
C8' N2' C12' C13' -177.1(9) . . . . ?
Ni1 N2' C12' C13' 2.7(11) . . . . ?
C10' C11' C12' N2' 1.6(13) . . . . ?
C10' C11' C12' C13' 176.9(8) . . . . ?
N2 C12 C13 N3 -10.9(18) . . . . ?
C11 C12 C13 N3 174.2(11) . . . . ?
C14 N3 C13 C12 -95.6(11) . . . . ?
C15 N3 C13 C12 145.0(9) . . . . ?
C13' N3 C13 C12 115.3(18) . . . . ?
Ni1 N3 C13 C12 13.0(12) . . . . ?
C14 N3 C13' C12' -79.1(6) . . . . ?
C15 N3 C13' C12' 161.5(5) . . . . ?
C13 N3 C13' C12' -42.4(11) . . . . ?
Ni1 N3 C13' C12' 41.7(6) . . . . ?
N2' C12' C13' N3 -31.9(10) . . . . ?
C11' C12' C13' N3 152.6(7) . . . . ?

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
C2 H2 F4 0.95 2.25 3.151(5) 158.0 4_575
C2 H2 F4' 0.95 2.54 3.450(14) 159.3 4_575
C4 H4 F1 0.95 2.61 3.452(5) 147.7 2_645
C4 H4 F2 0.95 2.50 3.114(5) 122.2 2_645
C4 H4 F1' 0.95 2.40 3.066(12) 126.4 2_645
C6 H6B F6' 0.99 2.27 3.146(9) 147.3 3_666
C14 H14A Cl1 0.99 2.78 3.590(4) 139.0 2
C15 H15C Cl1 0.98 2.96 3.564(4) 120.6 .
C7 H7A F5 0.99 2.58 3.309(10) 130.5 3_666
C7 H7B Cl2 0.99 2.69 3.400(10) 128.5 4_566
C11' H11' Cl2 0.95 2.89 3.711(9) 146.0 2
C13 H13A Cl1 0.99 2.82 3.660(12) 143.1 2
C16 H16A Cl1 0.98 2.89 3.487(13) 120.1 .
C16 H16B F5 0.98 2.60 3.399(12) 139.0 3_666
C16 H16C Cl2 0.98 2.62 3.160(13) 114.9 .
C13' H13D Cl1 0.99 2.98 3.860(9) 149.1 2
C13' H13D Cl2 0.99 2.75 3.583(7) 142.5 2

_refine_diff_density_max         0.702
_refine_diff_density_min         -0.614
_refine_diff_density_rms         0.101

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_33_a
_database_code_depnum_ccdc_archive 'CCDC 2076280'
loop_
_audit_author_name
_audit_author_address
'Liviu Mirica'
;University of Illinois at Urbana Champaign
United States of America
;
_audit_update_record             
;
2021-04-08 deposited with the CCDC.	2021-06-25 downloaded from the CCDC.
;
_audit_creation_date             2021-01-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H24 Cl N4 Ni O, C H Cl3, F6 P'
_chemical_formula_sum            'C18 H25 Cl4 F6 N4 Ni O P'
_chemical_formula_weight         658.90
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   19.4628(6)
_cell_length_b                   13.3212(4)
_cell_length_c                   9.6192(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2493.95(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    30469
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.467
_cell_measurement_theta_min      2.592
_shelx_estimated_absorpt_T_max   0.946
_shelx_estimated_absorpt_T_min   0.465
_exptl_absorpt_coefficient_mu    1.337
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1430 before and 0.0567 after correction.
The Ratio of minimum to maximum transmission is 0.8015.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.755
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1336
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2.00 0.00 3.00 0.2680
0.00 0.00 -1.00 0.3140
1.00 -3.00 0.00 0.0210
-1.00 3.00 0.00 0.0110
-4.00 1.00 -1.00 0.0830
4.00 -1.00 0.00 0.1100
-6.00 0.00 -1.00 0.0630
6.00 1.00 1.00 0.0790
-1.00 5.00 -1.00 0.0890
-4.00 -1.00 -1.00 0.0820

_exptl_crystal_size_max          0.676
_exptl_crystal_size_mid          0.159
_exptl_crystal_size_min          0.042
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            47334
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.489
_diffrn_reflns_theta_min         2.592
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.888
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                5629
_reflns_number_total             5725
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.698
_refine_diff_density_min         -1.291
_refine_diff_density_rms         0.123
_refine_ls_abs_structure_details 
;
 Flack x determined using 2592 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.015(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     359
_refine_ls_number_reflns         5725
_refine_ls_number_restraints     140
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0316
_refine_ls_restrained_S_all      1.036
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1040
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O1-H1
 0.87 with sigma of 0.01
 Ni1-H1
 2.655653 with sigma of 0.02
 C17-H1
 1.882317 with sigma of 0.02
 F6-F2 \\sim F6-F4 \\sim F2-F5 \\sim F5-F4 \\sim F6A-F2A \\sim F6A-F4A \\sim
F2A-F5A \\sim F5A-F4A
 with sigma of 0.04
 P1-F1 \\sim P1-F3 \\sim P1-F6 \\sim P1-F2 \\sim P1-F5 \\sim P1-F4 \\sim P1-F6A
\\sim P1-F2A \\sim P1-F5A \\sim P1-
 F4A
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 F6, F5, F4, F2, F3, F1, P1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F6A, F4A, F2A, F1, F3, F5A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(F6A)=Sof(F2A)=Sof(F5A)=Sof(F4A)=1-FVAR(1)
 Sof(F6)=Sof(F2)=Sof(F5)=Sof(F4)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C18(H18)
5.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C7(H7A,H7B), C6(H6A,H6B), C14(H14A,H14B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9), C11(H11), C3(H3), C10(H10), C4(H4)
5.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.70298(2) 0.32989(3) 0.50772(5) 0.01448(13) Uani 1 1 d D . . . .
Cl1 Cl 0.75707(4) 0.48826(6) 0.52076(10) 0.02148(19) Uani 1 1 d . . . . .
Cl2 Cl 0.45112(5) 1.13703(7) 0.69628(10) 0.0261(2) Uani 1 1 d . . . . .
Cl4 Cl 0.46625(5) 1.11750(8) 0.39788(10) 0.0300(2) Uani 1 1 d . . . . .
P1 P 0.52937(5) 0.66905(7) 0.53984(11) 0.0249(2) Uani 1 1 d D U . . .
Cl3 Cl 0.45219(5) 0.94093(8) 0.56400(13) 0.0343(2) Uani 1 1 d . . . . .
F1 F 0.53900(17) 0.7302(3) 0.6788(3) 0.0464(8) Uani 1 1 d D U . . .
N1 N 0.78694(14) 0.2469(2) 0.5474(3) 0.0168(5) Uani 1 1 d . . . . .
N4 N 0.73059(16) 0.2887(2) 0.2946(3) 0.0169(6) Uani 1 1 d . . . . .
O1 O 0.61489(13) 0.40885(19) 0.4590(3) 0.0239(5) Uani 1 1 d D . . . .
H1 H 0.6101(14) 0.4744(10) 0.466(6) 0.036 Uiso 1 1 d D U . . .
N2 N 0.65579(14) 0.1939(2) 0.4957(3) 0.0170(5) Uani 1 1 d . . . . .
F3 F 0.5221(3) 0.6076(3) 0.3995(4) 0.0687(11) Uani 1 1 d D U . . .
C1 C 0.81999(16) 0.2074(3) 0.4390(4) 0.0189(6) Uani 1 1 d . . . . .
C12 C 0.66412(17) 0.1414(3) 0.3779(4) 0.0170(6) Uani 1 1 d . . . . .
N3 N 0.68544(17) 0.3000(2) 0.7296(3) 0.0205(6) Uani 1 1 d . . . . .
C2 C 0.86658(18) 0.1292(3) 0.4585(5) 0.0235(7) Uani 1 1 d . . . . .
H2 H 0.8915 0.1021 0.3823 0.028 Uiso 1 1 calc R U . . .
C13 C 0.6844(2) 0.2039(3) 0.2541(4) 0.0196(6) Uani 1 1 d . . . . .
H13A H 0.7082 0.1608 0.1854 0.024 Uiso 1 1 calc R U . . .
H13B H 0.6425 0.2312 0.2095 0.024 Uiso 1 1 calc R U . . .
C8 C 0.63855(17) 0.1483(3) 0.6140(4) 0.0192(6) Uani 1 1 d . . . . .
C9 C 0.62540(18) 0.0454(3) 0.6181(4) 0.0234(7) Uani 1 1 d . . . . .
H9 H 0.6118 0.0136 0.7021 0.028 Uiso 1 1 calc R U . . .
C11 C 0.65336(17) 0.0385(3) 0.3751(4) 0.0203(7) Uani 1 1 d . . . . .
H11 H 0.6600 0.0015 0.2917 0.024 Uiso 1 1 calc R U . . .
C7 C 0.6335(2) 0.2174(3) 0.7377(4) 0.0257(8) Uani 1 1 d . . . . .
H7A H 0.5868 0.2468 0.7417 0.031 Uiso 1 1 calc R U . . .
H7B H 0.6409 0.1784 0.8240 0.031 Uiso 1 1 calc R U . . .
C3 C 0.87575(19) 0.0919(3) 0.5923(5) 0.0271(8) Uani 1 1 d . . . . .
H3 H 0.9075 0.0389 0.6083 0.033 Uiso 1 1 calc R U . . .
C5 C 0.79453(17) 0.2111(3) 0.6758(4) 0.0204(7) Uani 1 1 d . . . . .
C10 C 0.63266(18) -0.0096(2) 0.4962(5) 0.0241(7) Uani 1 1 d . . . . .
H10 H 0.6235 -0.0797 0.4957 0.029 Uiso 1 1 calc R U . . .
C6 C 0.7526(2) 0.2662(3) 0.7852(4) 0.0252(8) Uani 1 1 d . . . . .
H6A H 0.7448 0.2212 0.8655 0.030 Uiso 1 1 calc R U . . .
H6B H 0.7788 0.3252 0.8184 0.030 Uiso 1 1 calc R U . . .
C15 C 0.7240(2) 0.3708(3) 0.1929(4) 0.0253(7) Uani 1 1 d . . . . .
H15A H 0.6756 0.3903 0.1847 0.038 Uiso 1 1 calc R U . . .
H15B H 0.7410 0.3482 0.1023 0.038 Uiso 1 1 calc R U . . .
H15C H 0.7511 0.4286 0.2241 0.038 Uiso 1 1 calc R U . . .
C14 C 0.80317(19) 0.2552(3) 0.3012(4) 0.0225(7) Uani 1 1 d . . . . .
H14A H 0.8337 0.3136 0.2862 0.027 Uiso 1 1 calc R U . . .
H14B H 0.8119 0.2062 0.2258 0.027 Uiso 1 1 calc R U . . .
F6 F 0.5565(6) 0.7560(5) 0.4608(10) 0.051(3) Uani 0.413(9) 1 d D U P A 1
C4 C 0.8387(2) 0.1318(3) 0.7025(5) 0.0264(8) Uani 1 1 d . . . . .
H4 H 0.8435 0.1054 0.7938 0.032 Uiso 1 1 calc R U . . .
C18 C 0.4296(2) 1.0663(3) 0.5486(5) 0.0288(8) Uani 1 1 d . . . . .
H18 H 0.3785 1.0694 0.5376 0.035 Uiso 1 1 calc R U . . .
C16 C 0.6609(2) 0.3877(3) 0.8090(4) 0.0275(8) Uani 1 1 d . . . . .
H16A H 0.6953 0.4414 0.8042 0.041 Uiso 1 1 calc R U . . .
H16B H 0.6538 0.3684 0.9062 0.041 Uiso 1 1 calc R U . . .
H16C H 0.6175 0.4114 0.7693 0.041 Uiso 1 1 calc R U . . .
F2 F 0.6027(3) 0.6148(6) 0.5402(10) 0.038(2) Uani 0.413(9) 1 d D U P A 1
C17 C 0.54562(19) 0.3722(3) 0.4571(6) 0.0347(10) Uani 1 1 d D . . . .
H17A H 0.5435 0.3102 0.4024 0.052 Uiso 1 1 calc R U . . .
H17B H 0.5155 0.4228 0.4152 0.052 Uiso 1 1 calc R U . . .
H17C H 0.5305 0.3585 0.5524 0.052 Uiso 1 1 calc R U . . .
F5 F 0.5013(5) 0.5711(6) 0.6318(9) 0.051(3) Uani 0.413(9) 1 d D U P A 1
F4 F 0.4529(3) 0.7105(6) 0.5458(10) 0.051(3) Uani 0.413(9) 1 d D U P A 1
F6A F 0.4881(4) 0.7538(6) 0.4555(9) 0.074(2) Uani 0.587(9) 1 d D . P A 2
F2A F 0.5999(3) 0.7281(5) 0.4855(6) 0.0499(17) Uani 0.587(9) 1 d D . P A 2
F5A F 0.5762(4) 0.5892(4) 0.6096(9) 0.0528(18) Uani 0.587(9) 1 d D . P A 2
F4A F 0.4618(3) 0.6214(6) 0.5860(7) 0.061(3) Uani 0.587(9) 1 d D . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 Cl1 2.3611(8) . ?
Ni1 N1 2.009(3) . ?
Ni1 N4 2.189(3) . ?
Ni1 O1 2.065(3) . ?
Ni1 N2 2.034(3) . ?
Ni1 N3 2.197(3) . ?
Cl2 C18 1.756(4) . ?
Cl4 C18 1.754(4) . ?
P1 F1 1.576(3) . ?
P1 F3 1.585(3) . ?
P1 F6 1.483(7) . ?
P1 F2 1.600(6) . ?
P1 F5 1.668(7) . ?
P1 F4 1.588(6) . ?
P1 F6A 1.606(6) . ?
P1 F2A 1.667(5) . ?
P1 F5A 1.553(6) . ?
P1 F4A 1.527(5) . ?
Cl3 C18 1.734(4) . ?
N1 C1 1.334(5) . ?
N1 C5 1.333(5) . ?
N4 C13 1.496(4) . ?
N4 C15 1.473(5) . ?
N4 C14 1.483(4) . ?
O1 H1 0.881(13) . ?
O1 C17 1.434(4) . ?
N2 C12 1.342(4) . ?
N2 C8 1.333(5) . ?
C1 C2 1.393(5) . ?
C1 C14 1.506(5) . ?
C12 C13 1.505(5) . ?
C12 C11 1.388(5) . ?
N3 C7 1.496(5) . ?
N3 C6 1.483(5) . ?
N3 C16 1.474(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.392(6) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C8 C9 1.395(5) . ?
C8 C7 1.508(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.389(6) . ?
C11 H11 0.9500 . ?
C11 C10 1.390(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C3 H3 0.9500 . ?
C3 C4 1.387(6) . ?
C5 C6 1.521(6) . ?
C5 C4 1.387(5) . ?
C10 H10 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C4 H4 0.9500 . ?
C18 H18 1.0000 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ni1 Cl1 96.83(8) . . ?
N1 Ni1 N4 80.81(12) . . ?
N1 Ni1 O1 176.70(12) . . ?
N1 Ni1 N2 83.58(11) . . ?
N1 Ni1 N3 80.93(13) . . ?
N4 Ni1 Cl1 99.45(8) . . ?
N4 Ni1 N3 154.45(12) . . ?
O1 Ni1 Cl1 85.82(7) . . ?
O1 Ni1 N4 96.84(12) . . ?
O1 Ni1 N3 100.57(13) . . ?
N2 Ni1 Cl1 179.58(9) . . ?
N2 Ni1 N4 80.48(12) . . ?
N2 Ni1 O1 93.77(11) . . ?
N2 Ni1 N3 79.85(12) . . ?
N3 Ni1 Cl1 100.33(9) . . ?
F1 P1 F3 178.3(2) . . ?
F1 P1 F2 97.2(3) . . ?
F1 P1 F5 89.6(3) . . ?
F1 P1 F4 84.3(3) . . ?
F1 P1 F6A 97.1(4) . . ?
F1 P1 F2A 85.7(2) . . ?
F3 P1 F2 81.2(3) . . ?
F3 P1 F5 91.1(3) . . ?
F3 P1 F4 97.3(3) . . ?
F3 P1 F6A 83.6(4) . . ?
F3 P1 F2A 92.8(3) . . ?
F6 P1 F1 89.3(4) . . ?
F6 P1 F3 89.9(4) . . ?
F6 P1 F2 92.1(5) . . ?
F6 P1 F5 178.0(6) . . ?
F6 P1 F4 94.6(6) . . ?
F2 P1 F5 86.4(5) . . ?
F4 P1 F2 173.1(5) . . ?
F4 P1 F5 86.9(5) . . ?
F6A P1 F2A 85.5(4) . . ?
F5A P1 F1 85.3(3) . . ?
F5A P1 F3 93.8(3) . . ?
F5A P1 F6A 173.4(5) . . ?
F5A P1 F2A 88.6(4) . . ?
F4A P1 F1 94.1(3) . . ?
F4A P1 F3 87.5(3) . . ?
F4A P1 F6A 90.4(4) . . ?
F4A P1 F2A 175.9(5) . . ?
F4A P1 F5A 95.5(4) . . ?
C1 N1 Ni1 117.5(2) . . ?
C5 N1 Ni1 117.6(2) . . ?
C5 N1 C1 122.0(3) . . ?
C13 N4 Ni1 106.6(2) . . ?
C15 N4 Ni1 114.5(2) . . ?
C15 N4 C13 109.6(3) . . ?
C15 N4 C14 109.6(3) . . ?
C14 N4 Ni1 105.6(2) . . ?
C14 N4 C13 110.9(3) . . ?
Ni1 O1 H1 125.1(19) . . ?
C17 O1 Ni1 127.6(2) . . ?
C17 O1 H1 103.8(18) . . ?
C12 N2 Ni1 117.2(2) . . ?
C8 N2 Ni1 118.1(2) . . ?
C8 N2 C12 120.9(3) . . ?
N1 C1 C2 120.2(4) . . ?
N1 C1 C14 114.6(3) . . ?
C2 C1 C14 125.2(3) . . ?
N2 C12 C13 114.3(3) . . ?
N2 C12 C11 120.9(3) . . ?
C11 C12 C13 124.8(3) . . ?
C7 N3 Ni1 106.8(2) . . ?
C6 N3 Ni1 105.6(2) . . ?
C6 N3 C7 110.7(3) . . ?
C16 N3 Ni1 114.2(2) . . ?
C16 N3 C7 109.7(3) . . ?
C16 N3 C6 109.8(3) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.4(4) . . ?
C3 C2 H2 120.8 . . ?
N4 C13 C12 111.7(3) . . ?
N4 C13 H13A 109.3 . . ?
N4 C13 H13B 109.3 . . ?
C12 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
N2 C8 C9 121.2(3) . . ?
N2 C8 C7 114.3(3) . . ?
C9 C8 C7 124.5(3) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 C8 118.4(3) . . ?
C10 C9 H9 120.8 . . ?
C12 C11 H11 120.5 . . ?
C12 C11 C10 118.9(3) . . ?
C10 C11 H11 120.5 . . ?
N3 C7 C8 111.3(3) . . ?
N3 C7 H7A 109.4 . . ?
N3 C7 H7B 109.4 . . ?
C8 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
N1 C5 C6 114.1(3) . . ?
N1 C5 C4 120.9(4) . . ?
C4 C5 C6 125.0(4) . . ?
C9 C10 C11 119.6(3) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
N3 C6 C5 111.7(3) . . ?
N3 C6 H6A 109.3 . . ?
N3 C6 H6B 109.3 . . ?
C5 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
N4 C15 H15A 109.5 . . ?
N4 C15 H15B 109.5 . . ?
N4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N4 C14 C1 111.8(3) . . ?
N4 C14 H14A 109.2 . . ?
N4 C14 H14B 109.2 . . ?
C1 C14 H14A 109.2 . . ?
C1 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C3 C4 H4 120.9 . . ?
C5 C4 C3 118.2(4) . . ?
C5 C4 H4 120.9 . . ?
Cl2 C18 H18 107.5 . . ?
Cl4 C18 Cl2 111.3(2) . . ?
Cl4 C18 H18 107.5 . . ?
Cl3 C18 Cl2 112.8(3) . . ?
Cl3 C18 Cl4 110.0(2) . . ?
Cl3 C18 H18 107.5 . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ni1 N1 C1 C2 -163.1(3) . . . . ?
Ni1 N1 C1 C14 17.8(4) . . . . ?
Ni1 N1 C5 C6 -20.0(4) . . . . ?
Ni1 N1 C5 C4 161.5(3) . . . . ?
Ni1 N4 C13 C12 -29.9(3) . . . . ?
Ni1 N4 C14 C1 31.2(3) . . . . ?
Ni1 N2 C12 C13 -21.5(4) . . . . ?
Ni1 N2 C12 C11 159.4(3) . . . . ?
Ni1 N2 C8 C9 -160.7(3) . . . . ?
Ni1 N2 C8 C7 20.5(4) . . . . ?
Ni1 N3 C7 C8 30.2(4) . . . . ?
Ni1 N3 C6 C5 -31.0(4) . . . . ?
N1 C1 C2 C3 2.1(5) . . . . ?
N1 C1 C14 N4 -34.0(4) . . . . ?
N1 C5 C6 N3 35.2(4) . . . . ?
N1 C5 C4 C3 1.1(5) . . . . ?
N2 C12 C13 N4 35.1(4) . . . . ?
N2 C12 C11 C10 1.0(5) . . . . ?
N2 C8 C9 C10 1.9(5) . . . . ?
N2 C8 C7 N3 -34.5(5) . . . . ?
C1 N1 C5 C6 180.0(3) . . . . ?
C1 N1 C5 C4 1.4(5) . . . . ?
C1 C2 C3 C4 0.4(5) . . . . ?
C12 N2 C8 C9 -3.1(5) . . . . ?
C12 N2 C8 C7 178.1(3) . . . . ?
C12 C11 C10 C9 -2.1(5) . . . . ?
C2 C1 C14 N4 147.0(3) . . . . ?
C2 C3 C4 C5 -2.0(5) . . . . ?
C13 N4 C14 C1 -83.9(4) . . . . ?
C13 C12 C11 C10 -178.0(3) . . . . ?
C8 N2 C12 C13 -179.3(3) . . . . ?
C8 N2 C12 C11 1.6(5) . . . . ?
C8 C9 C10 C11 0.7(5) . . . . ?
C9 C8 C7 N3 146.8(4) . . . . ?
C11 C12 C13 N4 -145.9(3) . . . . ?
C7 N3 C6 C5 84.2(4) . . . . ?
C7 C8 C9 C10 -179.4(3) . . . . ?
C5 N1 C1 C2 -3.0(5) . . . . ?
C5 N1 C1 C14 177.9(3) . . . . ?
C6 N3 C7 C8 -84.3(4) . . . . ?
C6 C5 C4 C3 -177.2(4) . . . . ?
C15 N4 C13 C12 -154.3(3) . . . . ?
C15 N4 C14 C1 155.0(3) . . . . ?
C14 N4 C13 C12 84.6(4) . . . . ?
C14 C1 C2 C3 -179.0(3) . . . . ?
C4 C5 C6 N3 -146.3(4) . . . . ?
C16 N3 C7 C8 154.4(3) . . . . ?
C16 N3 C6 C5 -154.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
