# Supplementary Information (SI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2025

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 2394784'
loop_
_audit_author_name
_audit_author_address
'Maciej Kubicki'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2024-10-29 deposited with the CCDC.	2025-03-24 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 N2 Ni O2'
_chemical_formula_weight         379.09

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'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           52
_space_group_name_H-M_alt        'P n n a'
_space_group_name_Hall           '-P 2a 2bc'

_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+1/2, -y, z'
'-x+1/2, y+1/2, -z+1/2'
'x, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'x-1/2, -y-1/2, z-1/2'
'-x, y-1/2, z-1/2'

_cell_length_a                   6.81550(11)
_cell_length_b                   13.6335(2)
_cell_length_c                   17.8897(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1662.30(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(1)
_cell_measurement_reflns_used    7082
_cell_measurement_theta_min      2.4410
_cell_measurement_theta_max      74.1820

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.811
_shelx_estimated_absorpt_T_min   0.613
_shelx_estimated_absorpt_T_max   0.915
_exptl_absorpt_correction_T_min  0.66450
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.104a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      130(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.5384
_diffrn_reflns_number            12095
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.077
_diffrn_reflns_theta_max         74.406
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1698
_reflns_number_gt                1578
_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       
'CrysAlisPro system (CCD 43.104a 64-bit (release 22-12-2023))'
_computing_cell_refinement       'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXT-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0531P)²+0.6916P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     .
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1698
_refine_ls_number_parameters     114
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0979
_refine_ls_wR_factor_gt          0.0962
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_restrained_S_all      1.128
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.250000 0.500000 0.49173(2) 0.02449(16) Uani 1 2 d S T P . .
C1 C 0.3106(2) 0.31624(12) 0.42085(10) 0.0294(3) Uani 1 1 d . . . . .
O1 O 0.27894(17) 0.41076(8) 0.41475(6) 0.0292(3) Uani 1 1 d . . . . .
C2 C 0.3120(3) 0.25901(14) 0.35474(10) 0.0373(4) Uani 1 1 d . . . . .
H2 H 0.286266 0.289540 0.308026 0.045 Uiso 1 1 calc R U . . .
C3 C 0.3501(3) 0.15969(14) 0.35709(12) 0.0438(4) Uani 1 1 d . . . . .
H3 H 0.350407 0.123015 0.311941 0.053 Uiso 1 1 calc R U . . .
C4 C 0.3883(3) 0.11203(13) 0.42474(12) 0.0445(5) Uani 1 1 d . . . . .
H4 H 0.417516 0.043914 0.425751 0.053 Uiso 1 1 calc R U . . .
C5 C 0.3827(3) 0.16561(14) 0.48971(11) 0.0381(4) Uani 1 1 d . . . . .
H5 H 0.405955 0.133475 0.535985 0.046 Uiso 1 1 calc R U . . .
C6 C 0.3432(2) 0.26710(13) 0.48945(10) 0.0309(4) Uani 1 1 d . . . . .
C7 C 0.3386(2) 0.31838(12) 0.55935(10) 0.0325(4) Uani 1 1 d . . . . .
H7 H 0.365693 0.281599 0.603263 0.039 Uiso 1 1 calc R U . . .
N8 N 0.3008(2) 0.41042(10) 0.56743(8) 0.0299(3) Uani 1 1 d . . . . .
C9 C 0.3240(3) 0.45837(13) 0.64152(9) 0.0345(4) Uani 1 1 d . . . . .
H9 H 0.458429 0.487554 0.643951 0.041 Uiso 1 1 calc R U . . .
C10 C 0.2961(3) 0.39314(14) 0.70999(10) 0.0380(4) Uani 1 1 d . . . . .
H10A H 0.395789 0.340335 0.710109 0.046 Uiso 1 1 calc R U . . .
H10B H 0.164520 0.362406 0.708650 0.046 Uiso 1 1 calc R U . . .
C11 C 0.3169(3) 0.45579(15) 0.78056(10) 0.0462(5) Uani 1 1 d . . . . .
H11A H 0.287086 0.414833 0.824816 0.055 Uiso 1 1 calc R U . . .
H11B H 0.454609 0.478221 0.784947 0.055 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 O1 1.8481(11) 2_565 ?
Ni1 O1 1.8482(11) . ?
Ni1 N8 1.8561(14) . ?
Ni1 N8 1.8561(14) 2_565 ?
C1 O1 1.311(2) . ?
C1 C6 1.416(2) . ?
C1 C2 1.417(2) . ?
C2 C3 1.379(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.398(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.373(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.410(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.433(2) . ?
C7 N8 1.289(2) . ?
C7 H7 0.9500 . ?
N8 C9 1.486(2) . ?
C9 C9 1.518(4) 2_565 ?
C9 C10 1.526(2) . ?
C9 H9 1.0000 . ?
C10 C11 1.531(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C11 1.512(4) 2_565 ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Ni1 O1 83.66(7) 2_565 . ?
O1 Ni1 N8 175.34(5) 2_565 . ?
O1 Ni1 N8 95.19(6) . . ?
O1 Ni1 N8 95.19(6) 2_565 2_565 ?
O1 Ni1 N8 175.34(5) . 2_565 ?
N8 Ni1 N8 86.30(9) . 2_565 ?
O1 C1 C6 124.27(15) . . ?
O1 C1 C2 118.22(15) . . ?
C6 C1 C2 117.51(15) . . ?
C1 O1 Ni1 127.05(11) . . ?
C3 C2 C1 121.09(18) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 121.18(18) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 118.70(17) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.65(17) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 119.82(16) . . ?
C5 C6 C7 118.69(16) . . ?
C1 C6 C7 121.49(15) . . ?
N8 C7 C6 125.23(15) . . ?
N8 C7 H7 117.4 . . ?
C6 C7 H7 117.4 . . ?
C7 N8 C9 120.45(14) . . ?
C7 N8 Ni1 126.59(12) . . ?
C9 N8 Ni1 112.39(11) . . ?
N8 C9 C9 104.97(11) . 2_565 ?
N8 C9 C10 116.51(14) . . ?
C9 C9 C10 110.68(13) 2_565 . ?
N8 C9 H9 108.1 . . ?
C9 C9 H9 108.1 2_565 . ?
C10 C9 H9 108.1 . . ?
C9 C10 C11 108.98(15) . . ?
C9 C10 H10A 109.9 . . ?
C11 C10 H10A 109.9 . . ?
C9 C10 H10B 109.9 . . ?
C11 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
C11 C11 C10 112.88(15) 2_565 . ?
C11 C11 H11A 109.0 2_565 . ?
C10 C11 H11A 109.0 . . ?
C11 C11 H11B 109.0 2_565 . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?

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
C6 C1 O1 Ni1 -5.1(2) . . . . ?
C2 C1 O1 Ni1 174.76(12) . . . . ?
O1 Ni1 O1 C1 179.63(16) 2_565 . . . ?
N8 Ni1 O1 C1 4.17(14) . . . . ?
O1 C1 C2 C3 178.09(17) . . . . ?
C6 C1 C2 C3 -2.1(3) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C2 C3 C4 C5 1.5(3) . . . . ?
C3 C4 C5 C6 -1.2(3) . . . . ?
C4 C5 C6 C1 -0.8(3) . . . . ?
C4 C5 C6 C7 179.71(17) . . . . ?
O1 C1 C6 C5 -177.79(16) . . . . ?
C2 C1 C6 C5 2.4(2) . . . . ?
O1 C1 C6 C7 1.7(3) . . . . ?
C2 C1 C6 C7 -178.13(16) . . . . ?
C5 C6 C7 N8 -178.59(17) . . . . ?
C1 C6 C7 N8 1.9(3) . . . . ?
C6 C7 N8 C9 -172.50(16) . . . . ?
C6 C7 N8 Ni1 -1.8(3) . . . . ?
O1 Ni1 N8 C7 -0.78(16) . . . . ?
N8 Ni1 N8 C7 174.79(18) 2_565 . . . ?
O1 Ni1 N8 C9 170.52(11) . . . . ?
N8 Ni1 N8 C9 -13.91(8) 2_565 . . . ?
C7 N8 C9 C9 -151.19(17) . . . 2_565 ?
Ni1 N8 C9 C9 36.91(19) . . . 2_565 ?
C7 N8 C9 C10 -28.4(2) . . . . ?
Ni1 N8 C9 C10 159.72(13) . . . . ?
N8 C9 C10 C11 -177.67(16) . . . . ?
C9 C9 C10 C11 -57.9(2) 2_565 . . . ?
C9 C10 C11 C11 53.7(3) . . . 2_565 ?

_refine_diff_density_max         0.606
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.053



####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 2394786'
loop_
_audit_author_name
_audit_author_address
'Maciej Kubicki'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2024-10-29 deposited with the CCDC.	2025-03-24 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 N2 Ni O2'
_chemical_formula_sum            'C16 H14 N2 Ni O2'
_chemical_formula_weight         325.00

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'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   7.4766(3)
_cell_length_b                   13.8147(6)
_cell_length_c                   26.1363(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2699.5(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8796
_cell_measurement_theta_min      6.4081
_cell_measurement_theta_max      72.2037

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_F_000             1344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    2.122
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.760
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
J. Appl. Cryst. 48, 3-10.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec ImS DII'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω scans, π scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            25804
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.382
_diffrn_reflns_theta_max         72.359
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2665
_reflns_number_gt                2363
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0515P)²+1.2328P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     .
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0060(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2665
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1089
_refine_ls_wR_factor_gt          0.1057
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_restrained_S_all      1.162
_refine_ls_shift/su_max          0.002
_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 0.69047(5) 0.54800(2) 0.51148(2) 0.02810(17) Uani 1 1 d . . . . .
C1 C 0.6104(3) 0.62940(16) 0.41414(8) 0.0328(5) Uani 1 1 d . . . . .
O1 O 0.5959(2) 0.63353(10) 0.46403(6) 0.0328(4) Uani 1 1 d . . . . .
C2 C 0.5262(3) 0.70184(17) 0.38442(9) 0.0396(5) Uani 1 1 d . . . . .
H2 H 0.458558 0.749298 0.400636 0.048 Uiso 1 1 calc R U . . .
C3 C 0.5423(4) 0.7034(2) 0.33190(10) 0.0526(7) Uani 1 1 d . . . . .
H3 H 0.486188 0.752014 0.313230 0.063 Uiso 1 1 calc R U . . .
C4 C 0.6414(5) 0.6332(2) 0.30655(10) 0.0631(8) Uani 1 1 d . . . . .
H4 H 0.655766 0.636277 0.271239 0.076 Uiso 1 1 calc R U . . .
O4 O 0.6173(2) 0.63710(11) 0.55980(6) 0.0344(4) Uani 1 1 d . . . . .
C5 C 0.7175(4) 0.5599(2) 0.33366(11) 0.0549(7) Uani 1 1 d . . . . .
H5 H 0.780583 0.511942 0.316409 0.066 Uiso 1 1 calc R U . . .
C6 C 0.7024(3) 0.55510(17) 0.38779(9) 0.0375(5) Uani 1 1 d . . . . .
C7 C 0.7632(3) 0.47066(18) 0.41360(9) 0.0380(5) Uani 1 1 d . . . . .
H7 H 0.810317 0.420793 0.393855 0.046 Uiso 1 1 calc R U . . .
N8 N 0.7575(3) 0.45842(13) 0.46274(8) 0.0339(4) Uani 1 1 d . . . . .
C9 C 0.7957(4) 0.36223(18) 0.48430(10) 0.0442(6) Uani 1 1 d . . . . .
H9A H 0.878897 0.327538 0.462519 0.053 Uiso 1 1 calc R U . . .
H9B H 0.686358 0.324727 0.486873 0.053 Uiso 1 1 calc R U . . .
C10 C 0.8757(3) 0.37724(16) 0.53655(10) 0.0401(6) Uani 1 1 d . . . . .
H10A H 0.853012 0.321305 0.558024 0.048 Uiso 1 1 calc R U . . .
H10B H 1.003998 0.386320 0.533883 0.048 Uiso 1 1 calc R U . . .
N11 N 0.7910(2) 0.46452(13) 0.55887(8) 0.0322(4) Uani 1 1 d . . . . .
C12 C 0.7968(3) 0.47527(17) 0.60785(9) 0.0357(5) Uani 1 1 d . . . . .
H12 H 0.855715 0.427899 0.626703 0.043 Uiso 1 1 calc R U . . .
C13 C 0.7197(3) 0.55436(17) 0.63547(10) 0.0374(5) Uani 1 1 d . . . . .
C14 C 0.6252(3) 0.62891(15) 0.60986(8) 0.0310(5) Uani 1 1 d . . . . .
C15 C 0.5347(3) 0.69724(17) 0.64031(9) 0.0388(5) Uani 1 1 d . . . . .
H15 H 0.466735 0.745180 0.624604 0.047 Uiso 1 1 calc R U . . .
C16 C 0.5448(4) 0.6944(2) 0.69305(9) 0.0497(6) Uani 1 1 d . . . . .
H16 H 0.483390 0.740307 0.712291 0.060 Uiso 1 1 calc R U . . .
C17 C 0.6455(5) 0.6240(2) 0.71775(10) 0.0599(8) Uani 1 1 d . . . . .
H17 H 0.655512 0.624229 0.753212 0.072 Uiso 1 1 calc R U . . .
C18 C 0.7293(4) 0.5548(2) 0.68959(10) 0.0524(7) Uani 1 1 d . . . . .
H18 H 0.794201 0.506786 0.706208 0.063 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 N8 1.8456(19) . ?
Ni1 O4 1.8465(15) . ?
Ni1 N11 1.8516(19) . ?
Ni1 O1 1.8533(15) . ?
C1 O1 1.310(3) . ?
C1 C6 1.414(3) . ?
C1 C2 1.415(3) . ?
C2 C3 1.378(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.389(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.360(4) . ?
C4 H4 0.9300 . ?
O4 C14 1.315(3) . ?
C5 C6 1.421(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.422(3) . ?
C7 N8 1.296(3) . ?
C7 H7 0.9300 . ?
N8 C9 1.471(3) . ?
C9 C10 1.505(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N11 1.482(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
N11 C12 1.290(3) . ?
C12 C13 1.431(3) . ?
C12 H12 0.9300 . ?
C13 C18 1.416(4) . ?
C13 C14 1.417(3) . ?
C14 C15 1.408(3) . ?
C15 C16 1.381(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.389(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.359(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?

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
N8 Ni1 O4 178.52(8) . . ?
N8 Ni1 N11 86.20(9) . . ?
O4 Ni1 N11 94.48(8) . . ?
N8 Ni1 O1 93.97(8) . . ?
O4 Ni1 O1 85.39(7) . . ?
N11 Ni1 O1 178.38(7) . . ?
O1 C1 C6 123.8(2) . . ?
O1 C1 C2 118.6(2) . . ?
C6 C1 C2 117.6(2) . . ?
C1 O1 Ni1 127.35(14) . . ?
C3 C2 C1 121.3(2) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 120.7(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 119.6(3) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C14 O4 Ni1 127.58(14) . . ?
C4 C5 C6 121.4(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 119.3(2) . . ?
C1 C6 C7 121.3(2) . . ?
C5 C6 C7 119.0(2) . . ?
N8 C7 C6 124.5(2) . . ?
N8 C7 H7 117.7 . . ?
C6 C7 H7 117.7 . . ?
C7 N8 C9 119.4(2) . . ?
C7 N8 Ni1 127.26(17) . . ?
C9 N8 Ni1 113.19(15) . . ?
N8 C9 C10 107.46(19) . . ?
N8 C9 H9A 110.2 . . ?
C10 C9 H9A 110.2 . . ?
N8 C9 H9B 110.2 . . ?
C10 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
N11 C10 C9 107.42(19) . . ?
N11 C10 H10A 110.2 . . ?
C9 C10 H10A 110.2 . . ?
N11 C10 H10B 110.2 . . ?
C9 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
C12 N11 C10 118.0(2) . . ?
C12 N11 Ni1 127.30(16) . . ?
C10 N11 Ni1 114.65(16) . . ?
N11 C12 C13 125.1(2) . . ?
N11 C12 H12 117.4 . . ?
C13 C12 H12 117.4 . . ?
C18 C13 C14 119.6(2) . . ?
C18 C13 C12 119.1(2) . . ?
C14 C13 C12 121.2(2) . . ?
O4 C14 C15 118.9(2) . . ?
O4 C14 C13 123.7(2) . . ?
C15 C14 C13 117.4(2) . . ?
C16 C15 C14 121.3(2) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 C17 120.9(3) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C18 C17 C16 119.4(2) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C13 121.4(3) . . ?
C17 C18 H18 119.3 . . ?
C13 C18 H18 119.3 . . ?

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
C6 C1 O1 Ni1 1.0(3) . . . . ?
C2 C1 O1 Ni1 179.38(15) . . . . ?
N8 Ni1 O1 C1 -9.94(18) . . . . ?
O4 Ni1 O1 C1 171.39(18) . . . . ?
O1 C1 C2 C3 177.5(2) . . . . ?
C6 C1 C2 C3 -4.0(3) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C2 C3 C4 C5 2.7(5) . . . . ?
N11 Ni1 O4 C14 -6.33(19) . . . . ?
O1 Ni1 O4 C14 175.29(19) . . . . ?
C3 C4 C5 C6 -2.0(5) . . . . ?
O1 C1 C6 C5 -177.1(2) . . . . ?
C2 C1 C6 C5 4.5(3) . . . . ?
O1 C1 C6 C7 9.8(3) . . . . ?
C2 C1 C6 C7 -168.6(2) . . . . ?
C4 C5 C6 C1 -1.7(4) . . . . ?
C4 C5 C6 C7 171.6(3) . . . . ?
C1 C6 C7 N8 -7.4(4) . . . . ?
C5 C6 C7 N8 179.5(3) . . . . ?
C6 C7 N8 C9 169.7(2) . . . . ?
C6 C7 N8 Ni1 -5.8(4) . . . . ?
N11 Ni1 N8 C7 -166.1(2) . . . . ?
O1 Ni1 N8 C7 12.3(2) . . . . ?
N11 Ni1 N8 C9 18.20(17) . . . . ?
O1 Ni1 N8 C9 -163.42(17) . . . . ?
C7 N8 C9 C10 150.1(2) . . . . ?
Ni1 N8 C9 C10 -33.8(2) . . . . ?
N8 C9 C10 N11 33.7(3) . . . . ?
C9 C10 N11 C12 159.6(2) . . . . ?
C9 C10 N11 Ni1 -21.4(2) . . . . ?
N8 Ni1 N11 C12 -178.6(2) . . . . ?
O4 Ni1 N11 C12 0.1(2) . . . . ?
N8 Ni1 N11 C10 2.53(16) . . . . ?
O4 Ni1 N11 C10 -178.78(15) . . . . ?
C10 N11 C12 C13 -179.1(2) . . . . ?
Ni1 N11 C12 C13 2.1(3) . . . . ?
N11 C12 C13 C18 177.2(2) . . . . ?
N11 C12 C13 C14 1.0(4) . . . . ?
Ni1 O4 C14 C15 -169.09(15) . . . . ?
Ni1 O4 C14 C13 10.6(3) . . . . ?
C18 C13 C14 O4 176.3(2) . . . . ?
C12 C13 C14 O4 -7.5(3) . . . . ?
C18 C13 C14 C15 -4.0(3) . . . . ?
C12 C13 C14 C15 172.2(2) . . . . ?
O4 C14 C15 C16 -177.2(2) . . . . ?
C13 C14 C15 C16 3.1(3) . . . . ?
C14 C15 C16 C17 0.2(4) . . . . ?
C15 C16 C17 C18 -2.6(5) . . . . ?
C16 C17 C18 C13 1.6(5) . . . . ?
C14 C13 C18 C17 1.8(4) . . . . ?
C12 C13 C18 C17 -174.5(3) . . . . ?

_refine_diff_density_max         0.331
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.107



####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2394785'
loop_
_audit_author_name
_audit_author_address
'Maciej Kubicki'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2024-10-29 deposited with the CCDC.	2025-03-24 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H14 N2 Ni O2'
_chemical_formula_weight         373.04

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'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.3195(2)
_cell_length_b                   16.6342(8)
_cell_length_c                   17.1790(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1520.08(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    3988
_cell_measurement_theta_min      2.6810
_cell_measurement_theta_max      27.5670

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    1.293
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.42927
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.131a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.1544
_diffrn_reflns_number            10076
_diffrn_reflns_av_unetI/netI     0.0750
_diffrn_reflns_av_R_equivalents  0.0673
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.371
_diffrn_reflns_theta_max         28.173
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.881
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3275
_reflns_number_gt                2891
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.657
_reflns_Friedel_fraction_max     0.838
_reflns_Friedel_fraction_full    0.999

_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       
'CrysAlisPro system (CCD 43.105a 64-bit (release 11-01-2024))'
_computing_cell_refinement       'CrysAlisPro 1.171.43.131a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.131a (Rigaku OD, 2024)'
_computing_structure_solution    'SHELXT-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0732P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     .
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 962 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.019(15)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3275
_refine_ls_number_parameters     226
_refine_ls_number_restraints     141
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0570
_refine_ls_wR_factor_ref         0.1349
_refine_ls_wR_factor_gt          0.1280
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.045
_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 0.64411(13) 0.72436(4) 0.69154(4) 0.0161(2) Uani 1 1 d . . . . .
C1 C 1.0491(10) 0.7150(4) 0.7987(4) 0.0179(12) Uani 1 1 d . . . . .
O1 O 0.9260(8) 0.6838(3) 0.7401(3) 0.0215(10) Uani 1 1 d . . . . .
C2 C 1.2571(12) 0.6719(4) 0.8294(4) 0.0203(14) Uani 1 1 d . . . . .
H2 H 1.306079 0.622486 0.806240 0.024 Uiso 1 1 calc R U . . .
C3 C 1.3875(12) 0.7008(4) 0.8920(4) 0.0229(14) Uani 1 1 d . . . . .
H3 H 1.523523 0.670144 0.912156 0.028 Uiso 1 1 calc R U . . .
C4 C 1.3271(10) 0.7735(4) 0.9270(4) 0.0216(12) Uani 1 1 d . . . . .
H4 H 1.419826 0.792412 0.970582 0.026 Uiso 1 1 calc R U . . .
C5 C 1.1317(12) 0.8176(4) 0.8976(4) 0.0204(12) Uani 1 1 d . . . . .
H5 H 1.090989 0.867859 0.920551 0.024 Uiso 1 1 calc R U . . .
C6 C 0.9882(10) 0.7892(3) 0.8331(4) 0.0168(13) Uani 1 1 d . U . . .
C7 C 0.7932(10) 0.8393(4) 0.8038(4) 0.0185(13) Uani 1 1 d . . . . .
H7 H 0.765190 0.889135 0.829411 0.022 Uiso 1 1 calc R U . . .
N8 N 0.6493(9) 0.8219(3) 0.7444(3) 0.0154(10) Uani 1 1 d . . . . .
C9 C 0.4624(11) 0.8759(4) 0.7190(4) 0.0181(13) Uani 1 1 d . . . . .
C10 C 0.4310(11) 0.9550(4) 0.7441(4) 0.0206(14) Uani 1 1 d . . . . .
H10 H 0.546598 0.978120 0.779824 0.025 Uiso 1 1 calc R U . . .
C11 C 0.2305(12) 0.9996(4) 0.7166(4) 0.0228(14) Uani 1 1 d . . . . .
H11 H 0.203599 1.052554 0.735653 0.027 Uiso 1 1 calc R U . . .
C12 C 0.0687(11) 0.9678(4) 0.6615(4) 0.0214(14) Uani 1 1 d . . . . .
H12 H -0.068034 0.999079 0.642890 0.026 Uiso 1 1 calc R U . . .
C13 C 0.1043(11) 0.8912(4) 0.6335(4) 0.0212(14) Uani 1 1 d . . . . .
H13 H -0.005248 0.870064 0.594950 0.025 Uiso 1 1 calc R U . . .
C14 C 0.3017(11) 0.8445(4) 0.6620(4) 0.0179(13) Uani 1 1 d . . . . .
N15 N 0.3621(9) 0.7638(3) 0.6408(3) 0.0157(10) Uani 1 1 d . . . . .
C16 C 0.2191(10) 0.7228(4) 0.5931(4) 0.0187(12) Uani 1 1 d . . . . .
H16 H 0.073228 0.749152 0.573922 0.022 Uiso 1 1 calc R U . . .
C17 C 0.2606(11) 0.6435(4) 0.5674(4) 0.0165(13) Uani 1 1 d . . . . .
C18 C 0.4724(11) 0.5986(3) 0.5937(4) 0.0172(12) Uani 1 1 d . U . . .
O18 O 0.6394(8) 0.6265(2) 0.6421(2) 0.0204(9) Uani 1 1 d . . . . .
C19 C 0.4984(11) 0.5197(3) 0.5657(4) 0.0188(12) Uani 1 1 d . . . . .
H19 H 0.639660 0.488712 0.581211 0.023 Uiso 1 1 calc R U . . .
C20 C 0.3243(12) 0.4865(4) 0.5164(4) 0.0218(13) Uani 1 1 d . . . . .
H20 H 0.345781 0.432697 0.499091 0.026 Uiso 1 1 calc R U . . .
C21 C 0.1148(12) 0.5306(4) 0.4909(4) 0.0235(14) Uani 1 1 d . . . . .
H21 H -0.004742 0.507259 0.456647 0.028 Uiso 1 1 calc R U . . .
C22 C 0.0866(11) 0.6077(4) 0.5165(4) 0.0199(14) Uani 1 1 d . . . . .
H22 H -0.054326 0.638034 0.499427 0.024 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 O18 1.836(4) . ?
Ni1 O1 1.844(4) . ?
Ni1 N15 1.855(5) . ?
Ni1 N8 1.859(5) . ?
C1 O1 1.308(7) . ?
C1 C6 1.406(8) . ?
C1 C2 1.421(8) . ?
C2 C3 1.366(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.368(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.426(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.422(8) . ?
C7 N8 1.309(8) . ?
C7 H7 0.9500 . ?
N8 C9 1.409(8) . ?
C9 C10 1.395(9) . ?
C9 C14 1.401(9) . ?
C10 C11 1.382(9) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(9) . ?
C11 H11 0.9500 . ?
C12 C13 1.375(9) . ?
C12 H12 0.9500 . ?
C13 C14 1.394(9) . ?
C13 H13 0.9500 . ?
C14 N15 1.427(8) . ?
N15 C16 1.310(7) . ?
C16 C17 1.408(9) . ?
C16 H16 0.9500 . ?
C17 C22 1.406(8) . ?
C17 C18 1.425(8) . ?
C18 O18 1.303(7) . ?
C18 C19 1.404(8) . ?
C19 C20 1.371(8) . ?
C19 H19 0.9500 . ?
C20 C21 1.404(9) . ?
C20 H20 0.9500 . ?
C21 C22 1.364(8) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?

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
O18 Ni1 O1 84.03(19) . . ?
O18 Ni1 N15 94.89(19) . . ?
O1 Ni1 N15 178.8(2) . . ?
O18 Ni1 N8 178.3(2) . . ?
O1 Ni1 N8 95.0(2) . . ?
N15 Ni1 N8 86.1(2) . . ?
O1 C1 C6 123.8(5) . . ?
O1 C1 C2 118.4(6) . . ?
C6 C1 C2 117.8(6) . . ?
C1 O1 Ni1 127.6(4) . . ?
C3 C2 C1 120.7(6) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 121.9(6) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 118.8(6) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.1(6) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C7 122.3(6) . . ?
C1 C6 C5 119.6(5) . . ?
C7 C6 C5 118.1(5) . . ?
N8 C7 C6 124.9(6) . . ?
N8 C7 H7 117.5 . . ?
C6 C7 H7 117.5 . . ?
C7 N8 C9 120.9(5) . . ?
C7 N8 Ni1 125.6(4) . . ?
C9 N8 Ni1 113.3(4) . . ?
C10 C9 C14 119.6(6) . . ?
C10 C9 N8 126.2(6) . . ?
C14 C9 N8 114.2(5) . . ?
C11 C10 C9 119.6(6) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 120.5(6) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 120.5(6) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.8(6) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C9 119.8(6) . . ?
C13 C14 N15 127.1(6) . . ?
C9 C14 N15 113.0(5) . . ?
C16 N15 C14 121.2(5) . . ?
C16 N15 Ni1 125.4(4) . . ?
C14 N15 Ni1 113.3(4) . . ?
N15 C16 C17 126.4(6) . . ?
N15 C16 H16 116.8 . . ?
C17 C16 H16 116.8 . . ?
C22 C17 C16 119.2(5) . . ?
C22 C17 C18 119.7(5) . . ?
C16 C17 C18 121.0(6) . . ?
O18 C18 C19 119.0(5) . . ?
O18 C18 C17 123.7(5) . . ?
C19 C18 C17 117.3(6) . . ?
C18 O18 Ni1 128.4(4) . . ?
C20 C19 C18 121.4(6) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C19 C20 C21 121.2(6) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C22 C21 C20 118.6(6) . . ?
C22 C21 H21 120.7 . . ?
C20 C21 H21 120.7 . . ?
C21 C22 C17 121.8(6) . . ?
C21 C22 H22 119.1 . . ?
C17 C22 H22 119.1 . . ?

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
C6 C1 O1 Ni1 -2.7(8) . . . . ?
C2 C1 O1 Ni1 177.5(4) . . . . ?
O18 Ni1 O1 C1 -170.8(5) . . . . ?
N8 Ni1 O1 C1 7.8(5) . . . . ?
O1 C1 C2 C3 -178.1(5) . . . . ?
C6 C1 C2 C3 2.1(9) . . . . ?
C1 C2 C3 C4 -1.4(9) . . . . ?
C2 C3 C4 C5 -0.2(9) . . . . ?
C3 C4 C5 C6 1.1(9) . . . . ?
O1 C1 C6 C7 -3.6(9) . . . . ?
C2 C1 C6 C7 176.2(5) . . . . ?
O1 C1 C6 C5 179.0(5) . . . . ?
C2 C1 C6 C5 -1.2(8) . . . . ?
C4 C5 C6 C1 -0.4(9) . . . . ?
C4 C5 C6 C7 -177.9(5) . . . . ?
C1 C6 C7 N8 1.4(10) . . . . ?
C5 C6 C7 N8 178.8(5) . . . . ?
C6 C7 N8 C9 -179.3(5) . . . . ?
C6 C7 N8 Ni1 6.8(8) . . . . ?
O1 Ni1 N8 C7 -9.7(5) . . . . ?
N15 Ni1 N8 C7 170.9(5) . . . . ?
O1 Ni1 N8 C9 176.0(4) . . . . ?
N15 Ni1 N8 C9 -3.5(4) . . . . ?
C7 N8 C9 C10 9.9(9) . . . . ?
Ni1 N8 C9 C10 -175.5(5) . . . . ?
C7 N8 C9 C14 -171.7(5) . . . . ?
Ni1 N8 C9 C14 2.9(6) . . . . ?
C14 C9 C10 C11 4.8(9) . . . . ?
N8 C9 C10 C11 -176.9(6) . . . . ?
C9 C10 C11 C12 -3.3(10) . . . . ?
C10 C11 C12 C13 0.3(10) . . . . ?
C11 C12 C13 C14 1.3(10) . . . . ?
C12 C13 C14 C9 0.1(9) . . . . ?
C12 C13 C14 N15 178.5(6) . . . . ?
C10 C9 C14 C13 -3.2(9) . . . . ?
N8 C9 C14 C13 178.3(5) . . . . ?
C10 C9 C14 N15 178.2(5) . . . . ?
N8 C9 C14 N15 -0.3(7) . . . . ?
C13 C14 N15 C16 -4.2(9) . . . . ?
C9 C14 N15 C16 174.3(5) . . . . ?
C13 C14 N15 Ni1 179.1(5) . . . . ?
C9 C14 N15 Ni1 -2.4(6) . . . . ?
O18 Ni1 N15 C16 5.4(5) . . . . ?
N8 Ni1 N15 C16 -173.3(5) . . . . ?
O18 Ni1 N15 C14 -178.0(4) . . . . ?
N8 Ni1 N15 C14 3.3(4) . . . . ?
C14 N15 C16 C17 179.3(6) . . . . ?
Ni1 N15 C16 C17 -4.4(9) . . . . ?
N15 C16 C17 C22 179.3(6) . . . . ?
N15 C16 C17 C18 0.8(10) . . . . ?
C22 C17 C18 O18 -178.5(6) . . . . ?
C16 C17 C18 O18 0.0(10) . . . . ?
C22 C17 C18 C19 1.0(9) . . . . ?
C16 C17 C18 C19 179.5(6) . . . . ?
C19 C18 O18 Ni1 -176.5(4) . . . . ?
C17 C18 O18 Ni1 2.9(9) . . . . ?
O1 Ni1 O18 C18 175.8(5) . . . . ?
N15 Ni1 O18 C18 -4.8(5) . . . . ?
O18 C18 C19 C20 178.1(6) . . . . ?
C17 C18 C19 C20 -1.4(9) . . . . ?
C18 C19 C20 C21 1.0(10) . . . . ?
C19 C20 C21 C22 -0.2(9) . . . . ?
C20 C21 C22 C17 -0.2(9) . . . . ?
C16 C17 C22 C21 -178.8(6) . . . . ?
C18 C17 C22 C21 -0.2(9) . . . . ?

_refine_diff_density_max         0.912
_refine_diff_density_min         -1.081
_refine_diff_density_rms         0.136



