# Supplementary Information (SI) for RSC Advances.
# 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_AG004_100k_auto
_database_code_depnum_ccdc_archive 'CCDC 2355346'
loop_
_audit_author_name
_audit_author_address
'Armen Ayvazyan'
;Scientific Technological Center of Organic and Pharmaceutical Chemistry of NAS RA
Armenia
;
_audit_update_record             
;
2024-05-14 deposited with the CCDC.	2025-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C35 H36 N4 Ni O3'
_chemical_formula_sum            'C35 H36 N4 Ni O3'
_chemical_formula_weight         619.39

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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   9.8518(2)
_cell_length_b                   9.06380(10)
_cell_length_c                   16.7122(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.5980(10)
_cell_angle_gamma                90
_cell_volume                     1492.23(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    38341
_cell_measurement_theta_min      2.3820
_cell_measurement_theta_max      33.7380

_exptl_crystal_description       prism
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_F_000             652
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.693
_shelx_estimated_absorpt_T_min   0.819
_shelx_estimated_absorpt_T_max   0.934
_exptl_absorpt_correction_T_min  0.43958
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.92a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            54508
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.067
_diffrn_reflns_theta_max         33.599
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             10491
_reflns_number_gt                9696
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.833
_reflns_Friedel_fraction_max     0.855
_reflns_Friedel_fraction_full    1.000

_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 1.171.43.92a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 (Ferrugia, 2012)'
_computing_publication_material  'enCIFer version 1.7 (Allen et al., 2004)'

_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)+(0.0449P)²+0.2821P] 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 4169 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.013(4)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         10491
_refine_ls_number_parameters     388
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0805
_refine_ls_wR_factor_gt          0.0782
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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 0.61935(2) 0.52042(3) 0.19436(2) 0.01412(6) Uani 1 1 d . . . . .
O16 O 0.63788(15) 0.65120(17) 0.10880(8) 0.0189(3) Uani 1 1 d . . . . .
O25 O 0.52480(17) 0.14605(17) 0.29731(9) 0.0244(3) Uani 1 1 d . . . . .
O17 O 0.76871(16) 0.83564(18) 0.06555(9) 0.0223(3) Uani 1 1 d . . . . .
N39 N 0.49011(16) 0.4031(2) 0.13420(10) 0.0167(3) Uani 1 1 d . . . . .
N23 N 0.59377(16) 0.39101(18) 0.27956(9) 0.0148(3) Uani 1 1 d . . . . .
N18 N 1.11023(18) 0.1751(2) 0.12524(10) 0.0192(3) Uani 1 1 d . . . . .
N9 N 0.73713(16) 0.64224(18) 0.24998(9) 0.0141(3) Uani 1 1 d . . . . .
C6 C 0.62402(18) 0.5168(3) 0.52374(10) 0.0202(3) Uani 1 1 d . . . . .
H6 H 0.628484 0.545448 0.578380 0.024 Uiso 1 1 calc R U . . .
C12 C 0.96352(17) 0.5229(3) 0.14685(10) 0.0193(3) Uani 1 1 d . . . . .
C7 C 0.6846(2) 0.6011(2) 0.46517(11) 0.0178(3) Uani 1 1 d . . . . .
H7 H 0.731411 0.688594 0.480314 0.021 Uiso 1 1 calc R U . . .
C2 C 0.67904(18) 0.5611(2) 0.38309(10) 0.0142(3) Uani 1 1 d . . . . .
C26 C 0.82498(19) 0.7887(2) 0.36041(11) 0.0157(3) Uani 1 1 d . . . . .
C8 C 0.74661(18) 0.6605(2) 0.32696(11) 0.0143(3) Uani 1 1 d . . . . .
C15 C 0.7359(2) 0.7448(2) 0.11615(11) 0.0172(3) Uani 1 1 d . . . . .
C3 C 0.61006(19) 0.4301(2) 0.35996(11) 0.0156(3) Uani 1 1 d . . . . .
C5 C 0.5565(2) 0.3890(2) 0.50063(12) 0.0216(4) Uani 1 1 d . . . . .
H5 H 0.513244 0.330443 0.540011 0.026 Uiso 1 1 calc R U . . .
C40 C 0.5026(2) 0.2516(2) 0.16878(12) 0.0188(3) Uani 1 1 d . . . . .
H40 H 0.414618 0.197843 0.161789 0.023 Uiso 1 1 calc R U . . .
C30 C 1.0233(2) 0.8908(3) 0.42547(13) 0.0261(4) Uani 1 1 d . . . . .
H30 H 1.111171 0.878114 0.448442 0.031 Uiso 1 1 calc R U . . .
C43 C 0.5218(2) 0.3819(3) 0.04753(12) 0.0217(4) Uani 1 1 d . . . . .
H43A H 0.543571 0.476951 0.021482 0.026 Uiso 1 1 calc R U . . .
H43B H 0.445034 0.334860 0.018601 0.026 Uiso 1 1 calc R U . . .
C13 C 0.9831(2) 0.4044(2) 0.11749(12) 0.0202(4) Uani 1 1 d . . . . .
C38 C 0.3494(2) 0.4664(2) 0.14096(12) 0.0204(4) Uani 1 1 d . . . . .
H38A H 0.282668 0.391579 0.122823 0.024 Uiso 1 1 calc R U . . .
H38B H 0.341173 0.552714 0.104927 0.024 Uiso 1 1 calc R U . . .
C4 C 0.5510(2) 0.3456(2) 0.42161(12) 0.0206(4) Uani 1 1 d . . . . .
H4 H 0.506063 0.256037 0.408158 0.025 Uiso 1 1 calc R U . . .
C10 C 0.81521(19) 0.7357(2) 0.19505(11) 0.0158(3) Uani 1 1 d . . . . .
H10 H 0.824051 0.836917 0.218381 0.019 Uiso 1 1 calc R U . . .
C11 C 0.9578(2) 0.6718(2) 0.18100(12) 0.0191(4) Uani 1 1 d . . . . .
H11A H 1.006951 0.739454 0.144917 0.023 Uiso 1 1 calc R U . . .
H11B H 1.007410 0.670876 0.232827 0.023 Uiso 1 1 calc R U . . .
C14 C 1.0150(2) 0.2633(2) 0.07796(12) 0.0223(4) Uani 1 1 d . . . . .
H14A H 0.930162 0.206590 0.069567 0.027 Uiso 1 1 calc R U . . .
H14B H 1.054552 0.283351 0.024841 0.027 Uiso 1 1 calc R U . . .
C27 C 0.7659(2) 0.9287(2) 0.35864(12) 0.0204(4) Uani 1 1 d . . . . .
H27 H 0.677748 0.941713 0.336139 0.024 Uiso 1 1 calc R U . . .
C28 C 0.8362(3) 1.0489(2) 0.38984(13) 0.0268(5) Uani 1 1 d . . . . .
H28 H 0.796460 1.144378 0.388356 0.032 Uiso 1 1 calc R U . . .
C32 C 0.31523(17) 0.5135(3) 0.22503(11) 0.0202(3) Uani 1 1 d . . . . .
C29 C 0.9650(2) 1.0293(3) 0.42327(12) 0.0284(4) Uani 1 1 d . . . . .
H29 H 1.012863 1.111515 0.444661 0.034 Uiso 1 1 calc R U . . .
C35 C 0.2698(3) 0.5979(4) 0.38291(16) 0.0360(6) Uani 1 1 d . . . . .
H35 H 0.256435 0.625735 0.437055 0.043 Uiso 1 1 calc R U . . .
C24 C 0.5405(2) 0.2576(2) 0.25694(12) 0.0179(3) Uani 1 1 d . . . . .
C22 C 1.1629(2) 0.0489(2) 0.07931(13) 0.0243(4) Uani 1 1 d . . . . .
H22A H 1.230443 0.081675 0.039650 0.029 Uiso 1 1 calc R U . . .
H22B H 1.088412 -0.003633 0.051080 0.029 Uiso 1 1 calc R U . . .
C21 C 1.2286(2) -0.0495(2) 0.14290(14) 0.0251(4) Uani 1 1 d . . . . .
H21A H 1.327961 -0.033291 0.145486 0.030 Uiso 1 1 calc R U . . .
H21B H 1.210889 -0.154921 0.131410 0.030 Uiso 1 1 calc R U . . .
C42 C 0.6443(2) 0.2814(3) 0.05032(13) 0.0274(4) Uani 1 1 d . . . . .
H42A H 0.728333 0.338159 0.061329 0.033 Uiso 1 1 calc R U . . .
H42B H 0.654465 0.227514 -0.000804 0.033 Uiso 1 1 calc R U . . .
C19 C 1.0505(2) 0.1052(3) 0.19564(13) 0.0244(4) Uani 1 1 d . . . . .
H19A H 0.965442 0.052689 0.181494 0.029 Uiso 1 1 calc R U . . .
H19B H 1.031446 0.178748 0.237873 0.029 Uiso 1 1 calc R U . . .
C20 C 1.1608(3) -0.0021(3) 0.22222(13) 0.0286(5) Uani 1 1 d . . . . .
H20A H 1.121305 -0.088202 0.250030 0.034 Uiso 1 1 calc R U . . .
H20B H 1.227143 0.046651 0.258405 0.034 Uiso 1 1 calc R U . . .
C33 C 0.2518(2) 0.4166(3) 0.27721(14) 0.0254(4) Uani 1 1 d . . . . .
H33 H 0.223341 0.322077 0.259112 0.030 Uiso 1 1 calc R U . . .
C37 C 0.3524(2) 0.6533(3) 0.25168(14) 0.0254(4) Uani 1 1 d . . . . .
H37 H 0.394063 0.720535 0.215899 0.031 Uiso 1 1 calc R U . . .
C36 C 0.3289(3) 0.6953(3) 0.33006(16) 0.0331(5) Uani 1 1 d . . . . .
H36 H 0.353581 0.791406 0.347545 0.040 Uiso 1 1 calc R U . . .
C41 C 0.6138(3) 0.1746(3) 0.11921(14) 0.0300(5) Uani 1 1 d . . . . .
H41A H 0.696160 0.157148 0.152320 0.036 Uiso 1 1 calc R U . . .
H41B H 0.580789 0.078772 0.098235 0.036 Uiso 1 1 calc R U . . .
C34 C 0.2301(3) 0.4592(3) 0.35648(16) 0.0345(5) Uani 1 1 d . . . . .
H34 H 0.187985 0.392748 0.392472 0.041 Uiso 1 1 calc R U . . .
C31 C 0.9536(2) 0.7694(2) 0.39401(12) 0.0205(4) Uani 1 1 d . . . . .
H31 H 0.993862 0.674193 0.395544 0.025 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 N9 1.8459(16) . ?
Ni1 N23 1.8639(16) . ?
Ni1 O16 1.8677(14) . ?
Ni1 N39 1.9328(16) . ?
O16 C15 1.290(2) . ?
O25 C24 1.226(2) . ?
O17 C15 1.226(2) . ?
N39 C40 1.494(3) . ?
N39 C43 1.497(2) . ?
N39 C38 1.506(3) . ?
N23 C24 1.370(3) . ?
N23 C3 1.397(2) . ?
N18 C14 1.459(3) . ?
N18 C19 1.465(3) . ?
N18 C22 1.475(3) . ?
N9 C8 1.299(2) . ?
N9 C10 1.472(2) . ?
C6 C7 1.383(3) . ?
C6 C5 1.388(3) . ?
C6 H6 0.9500 . ?
C12 C13 1.197(3) . ?
C12 C11 1.467(3) . ?
C7 C2 1.419(2) . ?
C7 H7 0.9500 . ?
C2 C3 1.420(3) . ?
C2 C8 1.466(3) . ?
C26 C31 1.392(3) . ?
C26 C27 1.396(3) . ?
C26 C8 1.500(3) . ?
C15 C10 1.528(3) . ?
C3 C4 1.414(3) . ?
C5 C4 1.379(3) . ?
C5 H5 0.9500 . ?
C40 C24 1.517(3) . ?
C40 C41 1.547(3) . ?
C40 H40 1.0000 . ?
C30 C29 1.381(4) . ?
C30 C31 1.397(3) . ?
C30 H30 0.9500 . ?
C43 C42 1.512(3) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C13 C14 1.475(3) . ?
C38 C32 1.510(3) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C4 H4 0.9500 . ?
C10 C11 1.540(3) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C27 C28 1.390(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.392(3) . ?
C28 H28 0.9500 . ?
C32 C33 1.391(3) . ?
C32 C37 1.391(3) . ?
C29 H29 0.9500 . ?
C35 C36 1.382(4) . ?
C35 C34 1.387(4) . ?
C35 H35 0.9500 . ?
C22 C21 1.526(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C21 C20 1.551(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C42 C41 1.537(4) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C19 C20 1.522(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C33 C34 1.398(3) . ?
C33 H33 0.9500 . ?
C37 C36 1.386(3) . ?
C37 H37 0.9500 . ?
C36 H36 0.9500 . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C34 H34 0.9500 . ?
C31 H31 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
N9 Ni1 N23 94.65(7) . . ?
N9 Ni1 O16 86.56(6) . . ?
N23 Ni1 O16 177.83(7) . . ?
N9 Ni1 N39 176.61(8) . . ?
N23 Ni1 N39 87.57(7) . . ?
O16 Ni1 N39 91.15(7) . . ?
C15 O16 Ni1 115.05(12) . . ?
C40 N39 C43 103.81(16) . . ?
C40 N39 C38 113.15(16) . . ?
C43 N39 C38 108.87(15) . . ?
C40 N39 Ni1 104.67(11) . . ?
C43 N39 Ni1 115.53(12) . . ?
C38 N39 Ni1 110.70(12) . . ?
C24 N23 C3 121.93(16) . . ?
C24 N23 Ni1 113.52(12) . . ?
C3 N23 Ni1 124.06(13) . . ?
C14 N18 C19 114.22(17) . . ?
C14 N18 C22 111.76(16) . . ?
C19 N18 C22 103.25(17) . . ?
C8 N9 C10 120.76(16) . . ?
C8 N9 Ni1 127.81(13) . . ?
C10 N9 Ni1 111.11(11) . . ?
C7 C6 C5 118.26(17) . . ?
C7 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
C13 C12 C11 172.71(19) . . ?
C6 C7 C2 122.01(19) . . ?
C6 C7 H7 119.0 . . ?
C2 C7 H7 119.0 . . ?
C7 C2 C3 119.38(17) . . ?
C7 C2 C8 116.61(16) . . ?
C3 C2 C8 124.01(16) . . ?
C31 C26 C27 120.02(18) . . ?
C31 C26 C8 121.09(17) . . ?
C27 C26 C8 118.88(17) . . ?
N9 C8 C2 121.79(17) . . ?
N9 C8 C26 119.95(17) . . ?
C2 C8 C26 118.24(15) . . ?
O17 C15 O16 125.33(18) . . ?
O17 C15 C10 119.68(17) . . ?
O16 C15 C10 114.98(16) . . ?
N23 C3 C4 121.29(17) . . ?
N23 C3 C2 121.58(16) . . ?
C4 C3 C2 117.02(17) . . ?
C4 C5 C6 121.26(18) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
N39 C40 C24 111.16(16) . . ?
N39 C40 C41 105.28(17) . . ?
C24 C40 C41 111.57(17) . . ?
N39 C40 H40 109.6 . . ?
C24 C40 H40 109.6 . . ?
C41 C40 H40 109.6 . . ?
C29 C30 C31 120.2(2) . . ?
C29 C30 H30 119.9 . . ?
C31 C30 H30 119.9 . . ?
N39 C43 C42 102.84(16) . . ?
N39 C43 H43A 111.2 . . ?
C42 C43 H43A 111.2 . . ?
N39 C43 H43B 111.2 . . ?
C42 C43 H43B 111.2 . . ?
H43A C43 H43B 109.1 . . ?
C12 C13 C14 175.9(2) . . ?
N39 C38 C32 113.09(15) . . ?
N39 C38 H38A 109.0 . . ?
C32 C38 H38A 109.0 . . ?
N39 C38 H38B 109.0 . . ?
C32 C38 H38B 109.0 . . ?
H38A C38 H38B 107.8 . . ?
C5 C4 C3 122.05(19) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
N9 C10 C15 107.65(15) . . ?
N9 C10 C11 111.22(16) . . ?
C15 C10 C11 110.36(15) . . ?
N9 C10 H10 109.2 . . ?
C15 C10 H10 109.2 . . ?
C11 C10 H10 109.2 . . ?
C12 C11 C10 116.38(16) . . ?
C12 C11 H11A 108.2 . . ?
C10 C11 H11A 108.2 . . ?
C12 C11 H11B 108.2 . . ?
C10 C11 H11B 108.2 . . ?
H11A C11 H11B 107.3 . . ?
N18 C14 C13 111.81(17) . . ?
N18 C14 H14A 109.3 . . ?
C13 C14 H14A 109.3 . . ?
N18 C14 H14B 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
C28 C27 C26 119.9(2) . . ?
C28 C27 H27 120.1 . . ?
C26 C27 H27 120.1 . . ?
C27 C28 C29 119.9(2) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C33 C32 C37 119.55(19) . . ?
C33 C32 C38 120.7(2) . . ?
C37 C32 C38 119.7(2) . . ?
C30 C29 C28 120.3(2) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C36 C35 C34 119.6(2) . . ?
C36 C35 H35 120.2 . . ?
C34 C35 H35 120.2 . . ?
O25 C24 N23 128.77(18) . . ?
O25 C24 C40 118.27(18) . . ?
N23 C24 C40 112.92(17) . . ?
N18 C22 C21 103.87(17) . . ?
N18 C22 H22A 111.0 . . ?
C21 C22 H22A 111.0 . . ?
N18 C22 H22B 111.0 . . ?
C21 C22 H22B 111.0 . . ?
H22A C22 H22B 109.0 . . ?
C22 C21 C20 104.46(18) . . ?
C22 C21 H21A 110.9 . . ?
C20 C21 H21A 110.9 . . ?
C22 C21 H21B 110.9 . . ?
C20 C21 H21B 110.9 . . ?
H21A C21 H21B 108.9 . . ?
C43 C42 C41 103.89(18) . . ?
C43 C42 H42A 111.0 . . ?
C41 C42 H42A 111.0 . . ?
C43 C42 H42B 111.0 . . ?
C41 C42 H42B 111.0 . . ?
H42A C42 H42B 109.0 . . ?
N18 C19 C20 102.64(17) . . ?
N18 C19 H19A 111.2 . . ?
C20 C19 H19A 111.2 . . ?
N18 C19 H19B 111.2 . . ?
C20 C19 H19B 111.2 . . ?
H19A C19 H19B 109.2 . . ?
C19 C20 C21 103.91(17) . . ?
C19 C20 H20A 111.0 . . ?
C21 C20 H20A 111.0 . . ?
C19 C20 H20B 111.0 . . ?
C21 C20 H20B 111.0 . . ?
H20A C20 H20B 109.0 . . ?
C32 C33 C34 119.6(2) . . ?
C32 C33 H33 120.2 . . ?
C34 C33 H33 120.2 . . ?
C36 C37 C32 120.4(2) . . ?
C36 C37 H37 119.8 . . ?
C32 C37 H37 119.8 . . ?
C35 C36 C37 120.3(3) . . ?
C35 C36 H36 119.8 . . ?
C37 C36 H36 119.8 . . ?
C42 C41 C40 105.19(18) . . ?
C42 C41 H41A 110.7 . . ?
C40 C41 H41A 110.7 . . ?
C42 C41 H41B 110.7 . . ?
C40 C41 H41B 110.7 . . ?
H41A C41 H41B 108.8 . . ?
C35 C34 C33 120.4(3) . . ?
C35 C34 H34 119.8 . . ?
C33 C34 H34 119.8 . . ?
C26 C31 C30 119.7(2) . . ?
C26 C31 H31 120.2 . . ?
C30 C31 H31 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N9 Ni1 O16 C15 12.82(14) . . . . ?
N39 Ni1 O16 C15 -169.67(14) . . . . ?
N9 Ni1 N23 C24 -162.55(14) . . . . ?
N39 Ni1 N23 C24 20.02(14) . . . . ?
N9 Ni1 N23 C3 25.29(15) . . . . ?
N39 Ni1 N23 C3 -152.15(15) . . . . ?
N23 Ni1 N9 C8 -24.44(17) . . . . ?
O16 Ni1 N9 C8 153.75(17) . . . . ?
N23 Ni1 N9 C10 162.15(13) . . . . ?
O16 Ni1 N9 C10 -19.66(13) . . . . ?
C5 C6 C7 C2 0.2(3) . . . . ?
C6 C7 C2 C3 -0.4(3) . . . . ?
C6 C7 C2 C8 179.59(18) . . . . ?
C10 N9 C8 C2 -174.74(16) . . . . ?
Ni1 N9 C8 C2 12.4(3) . . . . ?
C10 N9 C8 C26 7.1(3) . . . . ?
Ni1 N9 C8 C26 -165.77(14) . . . . ?
C7 C2 C8 N9 -173.44(17) . . . . ?
C3 C2 C8 N9 6.5(3) . . . . ?
C7 C2 C8 C26 4.8(2) . . . . ?
C3 C2 C8 C26 -175.25(17) . . . . ?
C31 C26 C8 N9 -104.1(2) . . . . ?
C27 C26 C8 N9 76.9(2) . . . . ?
C31 C26 C8 C2 77.6(2) . . . . ?
C27 C26 C8 C2 -101.4(2) . . . . ?
Ni1 O16 C15 O17 176.81(17) . . . . ?
Ni1 O16 C15 C10 -2.4(2) . . . . ?
C24 N23 C3 C4 -11.2(3) . . . . ?
Ni1 N23 C3 C4 160.31(15) . . . . ?
C24 N23 C3 C2 172.86(17) . . . . ?
Ni1 N23 C3 C2 -15.6(2) . . . . ?
C7 C2 C3 N23 175.61(17) . . . . ?
C8 C2 C3 N23 -4.4(3) . . . . ?
C7 C2 C3 C4 -0.5(3) . . . . ?
C8 C2 C3 C4 179.54(17) . . . . ?
C7 C6 C5 C4 0.8(3) . . . . ?
C43 N39 C40 C24 152.89(16) . . . . ?
C38 N39 C40 C24 -89.26(19) . . . . ?
Ni1 N39 C40 C24 31.35(18) . . . . ?
C43 N39 C40 C41 31.92(19) . . . . ?
C38 N39 C40 C41 149.78(17) . . . . ?
Ni1 N39 C40 C41 -89.61(15) . . . . ?
C40 N39 C43 C42 -44.04(19) . . . . ?
C38 N39 C43 C42 -164.82(17) . . . . ?
Ni1 N39 C43 C42 69.94(19) . . . . ?
C40 N39 C38 C32 73.8(2) . . . . ?
C43 N39 C38 C32 -171.33(19) . . . . ?
Ni1 N39 C38 C32 -43.3(2) . . . . ?
C6 C5 C4 C3 -1.8(3) . . . . ?
N23 C3 C4 C5 -174.54(19) . . . . ?
C2 C3 C4 C5 1.6(3) . . . . ?
C8 N9 C10 C15 -152.02(17) . . . . ?
Ni1 N9 C10 C15 21.92(18) . . . . ?
C8 N9 C10 C11 87.0(2) . . . . ?
Ni1 N9 C10 C11 -99.09(15) . . . . ?
O17 C15 C10 N9 167.99(18) . . . . ?
O16 C15 C10 N9 -12.7(2) . . . . ?
O17 C15 C10 C11 -70.5(2) . . . . ?
O16 C15 C10 C11 108.81(19) . . . . ?
N9 C10 C11 C12 59.4(2) . . . . ?
C15 C10 C11 C12 -60.0(2) . . . . ?
C19 N18 C14 C13 74.5(2) . . . . ?
C22 N18 C14 C13 -168.77(18) . . . . ?
C31 C26 C27 C28 0.6(3) . . . . ?
C8 C26 C27 C28 179.53(19) . . . . ?
C26 C27 C28 C29 -0.4(3) . . . . ?
N39 C38 C32 C33 -91.9(2) . . . . ?
N39 C38 C32 C37 85.5(2) . . . . ?
C31 C30 C29 C28 0.1(3) . . . . ?
C27 C28 C29 C30 0.1(3) . . . . ?
C3 N23 C24 O25 -15.6(3) . . . . ?
Ni1 N23 C24 O25 172.08(18) . . . . ?
C3 N23 C24 C40 167.02(17) . . . . ?
Ni1 N23 C24 C40 -5.3(2) . . . . ?
N39 C40 C24 O25 163.92(18) . . . . ?
C41 C40 C24 O25 -78.9(2) . . . . ?
N39 C40 C24 N23 -18.4(2) . . . . ?
C41 C40 C24 N23 98.8(2) . . . . ?
C14 N18 C22 C21 -165.85(17) . . . . ?
C19 N18 C22 C21 -42.6(2) . . . . ?
N18 C22 C21 C20 21.2(2) . . . . ?
N39 C43 C42 C41 38.4(2) . . . . ?
C14 N18 C19 C20 168.54(17) . . . . ?
C22 N18 C19 C20 47.0(2) . . . . ?
N18 C19 C20 C21 -32.4(2) . . . . ?
C22 C21 C20 C19 6.7(2) . . . . ?
C37 C32 C33 C34 -2.1(3) . . . . ?
C38 C32 C33 C34 175.4(2) . . . . ?
C33 C32 C37 C36 1.3(3) . . . . ?
C38 C32 C37 C36 -176.21(19) . . . . ?
C34 C35 C36 C37 -2.0(4) . . . . ?
C32 C37 C36 C35 0.8(3) . . . . ?
C43 C42 C41 C40 -18.6(2) . . . . ?
N39 C40 C41 C42 -8.0(2) . . . . ?
C24 C40 C41 C42 -128.66(19) . . . . ?
C36 C35 C34 C33 1.1(4) . . . . ?
C32 C33 C34 C35 0.9(4) . . . . ?
C27 C26 C31 C30 -0.3(3) . . . . ?
C8 C26 C31 C30 -179.28(18) . . . . ?
C29 C30 C31 C26 0.0(3) . . . . ?

_refine_diff_density_max         0.954
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_ANNA100K
_database_code_depnum_ccdc_archive 'CCDC 2355349'
loop_
_audit_author_name
_audit_author_address
'Armen Ayvazyan'
;Scientific Technological Center of Organic and Pharmaceutical Chemistry of NAS RA
Armenia
;
_audit_update_record             
;
2024-05-14 deposited with the CCDC.	2025-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C35 H38 N4 Ni O3'
_chemical_formula_sum            'C35 H38 N4 Ni O3'
_chemical_formula_weight         621.40

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                   8.06690(10)
_cell_length_b                   11.45850(10)
_cell_length_c                   32.7459(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3026.85(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    86163
_cell_measurement_theta_min      2.1720
_cell_measurement_theta_max      33.7630

_exptl_crystal_description       prism
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_F_000             1312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.683
_shelx_estimated_absorpt_T_min   0.811
_shelx_estimated_absorpt_T_max   0.935
_exptl_absorpt_correction_T_min  0.66803
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.92a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      100.0(8)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            113657
_diffrn_reflns_av_unetI/netI     0.0109
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_theta_min         2.169
_diffrn_reflns_theta_max         33.665
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             11103
_reflns_number_gt                10858
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.749
_reflns_Friedel_fraction_max     0.891
_reflns_Friedel_fraction_full    1.000

_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 1.171.43.92a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 (Ferrugia, 2012)'
_computing_publication_material  'enCIFer version 1.7 (Allen et al., 2004)'

_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)+(0.0353P)²+0.4937P] 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 4562 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0000(15)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         11103
_refine_ls_number_parameters     390
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0227
_refine_ls_R_factor_gt           0.0220
_refine_ls_wR_factor_ref         0.0595
_refine_ls_wR_factor_gt          0.0592
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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 0.46406(2) 0.49644(2) 0.34003(2) 0.01156(4) Uani 1 1 d . . . . .
C2 C 0.41787(15) 0.66056(10) 0.40609(3) 0.01367(19) Uani 1 1 d . . . . .
C3 C 0.55837(15) 0.61295(10) 0.42671(3) 0.01378(19) Uani 1 1 d . . . . .
C4 C 0.62543(17) 0.67329(11) 0.46063(4) 0.0192(2) Uani 1 1 d . . . . .
H4 H 0.717568 0.640475 0.474576 0.023 Uiso 1 1 calc R U . . .
C5 C 0.56157(19) 0.77811(11) 0.47412(4) 0.0222(2) Uani 1 1 d . . . . .
H5 H 0.608787 0.817094 0.496931 0.027 Uiso 1 1 calc R U . . .
C6 C 0.42631(18) 0.82547(11) 0.45354(4) 0.0209(2) Uani 1 1 d . . . . .
H6 H 0.382219 0.898269 0.462181 0.025 Uiso 1 1 calc R U . . .
C7 C 0.35513(17) 0.76841(11) 0.42077(4) 0.0188(2) Uani 1 1 d . . . . .
H7 H 0.261632 0.802282 0.407705 0.023 Uiso 1 1 calc R U . . .
N8 N 0.35299(12) 0.60710(9) 0.37121(3) 0.01316(16) Uani 1 1 d . . . . .
C9 C 0.20478(15) 0.64125(10) 0.35480(4) 0.01464(19) Uani 1 1 d . . . . .
O10 O 0.09508(12) 0.70008(9) 0.37092(3) 0.02017(17) Uani 1 1 d . . . . .
C11 C 0.64056(12) 0.50410(11) 0.41486(3) 0.01248(16) Uani 1 1 d . . . . .
N12 N 0.60063(12) 0.44701(8) 0.38204(3) 0.01170(16) Uani 1 1 d . . . . .
C13 C 0.68476(14) 0.33667(10) 0.37153(3) 0.01260(18) Uani 1 1 d . . . . .
H13 H 0.802684 0.341628 0.380782 0.015 Uiso 1 1 calc R U . . .
C14 C 0.60387(15) 0.22887(10) 0.39165(4) 0.0164(2) Uani 1 1 d . . . . .
H14A H 0.653021 0.157762 0.379470 0.020 Uiso 1 1 calc R U . . .
H14B H 0.632087 0.228957 0.421072 0.020 Uiso 1 1 calc R U . . .
C15 C 0.42229(15) 0.22193(10) 0.38756(4) 0.0171(2) Uani 1 1 d . . . . .
C16 C 0.27376(16) 0.21487(11) 0.38629(4) 0.0185(2) Uani 1 1 d . . . . .
C17 C 0.08958(15) 0.20901(11) 0.38435(4) 0.0181(2) Uani 1 1 d . . . . .
H17A H 0.044200 0.263673 0.404917 0.022 Uiso 1 1 calc R U . . .
H17B H 0.054199 0.237369 0.357152 0.022 Uiso 1 1 calc R U . . .
N18 N 0.01459(13) 0.09463(9) 0.39111(3) 0.01653(18) Uani 1 1 d . . . . .
C19 C 0.03196(19) 0.05803(13) 0.43391(4) 0.0242(2) Uani 1 1 d . . . . .
H19A H 0.006452 0.125152 0.451883 0.029 Uiso 1 1 calc R U . . .
H19B H 0.148468 0.035011 0.438949 0.029 Uiso 1 1 calc R U . . .
C20 C -0.0811(2) -0.04334(17) 0.44511(5) 0.0360(4) Uani 1 1 d . . . . .
H20A H -0.045280 -0.113621 0.430511 0.054 Uiso 1 1 calc R U . . .
H20B H -0.195361 -0.024452 0.437429 0.054 Uiso 1 1 calc R U . . .
H20C H -0.075317 -0.057244 0.474607 0.054 Uiso 1 1 calc R U . . .
C21 C 0.08087(15) 0.00569(12) 0.36325(4) 0.0196(2) Uani 1 1 d . . . . .
H21A H 0.022959 -0.069135 0.368246 0.023 Uiso 1 1 calc R U . . .
H21B H 0.199992 -0.006221 0.369213 0.023 Uiso 1 1 calc R U . . .
C22 C 0.06094(19) 0.03912(14) 0.31845(4) 0.0264(3) Uani 1 1 d . . . . .
H22A H 0.079384 -0.029744 0.301293 0.040 Uiso 1 1 calc R U . . .
H22B H 0.141961 0.099592 0.311419 0.040 Uiso 1 1 calc R U . . .
H22C H -0.051351 0.068990 0.313843 0.040 Uiso 1 1 calc R U . . .
C23 C 0.68248(14) 0.32517(11) 0.32493(4) 0.01485(19) Uani 1 1 d . . . . .
O24 O 0.77295(12) 0.25394(9) 0.30825(3) 0.02260(19) Uani 1 1 d . . . . .
O25 O 0.58081(11) 0.39458(8) 0.30647(3) 0.01733(16) Uani 1 1 d . . . . .
C26 C 0.50520(15) 0.72904(11) 0.29429(4) 0.0172(2) Uani 1 1 d . . . . .
C27 C 0.42430(16) 0.83450(12) 0.30144(4) 0.0211(2) Uani 1 1 d . . . . .
H27 H 0.318059 0.847879 0.289835 0.025 Uiso 1 1 calc R U . . .
C28 C 0.49774(18) 0.92049(12) 0.32545(5) 0.0245(3) Uani 1 1 d . . . . .
H28 H 0.441677 0.992170 0.330104 0.029 Uiso 1 1 calc R U . . .
C29 C 0.65302(19) 0.90147(13) 0.34260(5) 0.0254(3) Uani 1 1 d . . . . .
H29 H 0.702746 0.959817 0.359170 0.030 Uiso 1 1 calc R U . . .
C30 C 0.73561(17) 0.79667(13) 0.33543(5) 0.0254(3) Uani 1 1 d . . . . .
H30 H 0.841651 0.783247 0.347141 0.031 Uiso 1 1 calc R U . . .
C31 C 0.66239(16) 0.71205(12) 0.31113(4) 0.0210(2) Uani 1 1 d . . . . .
H31 H 0.720087 0.641366 0.305861 0.025 Uiso 1 1 calc R U . . .
C32 C 0.42666(16) 0.63405(11) 0.26906(4) 0.0190(2) Uani 1 1 d . . . . .
H32A H 0.350794 0.670123 0.248927 0.023 Uiso 1 1 calc R U . . .
H32B H 0.514528 0.592668 0.253704 0.023 Uiso 1 1 calc R U . . .
N33 N 0.33126(12) 0.54667(9) 0.29403(3) 0.01406(17) Uani 1 1 d . . . . .
C34 C 0.17523(15) 0.59450(11) 0.31206(4) 0.0170(2) Uani 1 1 d . . . . .
H34 H 0.132139 0.658639 0.294283 0.020 Uiso 1 1 calc R U . . .
C35 C 0.05036(17) 0.49068(15) 0.31173(5) 0.0303(3) Uani 1 1 d . . . . .
H35A H 0.015421 0.470773 0.339861 0.036 Uiso 1 1 calc R U . . .
H35B H -0.049215 0.510474 0.295472 0.036 Uiso 1 1 calc R U . . .
C36 C 0.14443(18) 0.38900(13) 0.29228(4) 0.0231(2) Uani 1 1 d . . . . .
H36A H 0.196033 0.338794 0.313346 0.028 Uiso 1 1 calc R U . . .
H36B H 0.070206 0.340891 0.275068 0.028 Uiso 1 1 calc R U . . .
C37 C 0.27431(16) 0.44968(12) 0.26678(4) 0.0184(2) Uani 1 1 d . . . . .
H37A H 0.366751 0.396210 0.260040 0.022 Uiso 1 1 calc R U . . .
H37B H 0.226167 0.480487 0.241141 0.022 Uiso 1 1 calc R U . . .
C38 C 0.78181(15) 0.46261(10) 0.44106(3) 0.01293(18) Uani 1 1 d . . . . .
C39 C 0.94135(14) 0.50385(11) 0.43260(3) 0.01596(18) Uani 1 1 d . . . . .
H39 H 0.958805 0.556145 0.410500 0.019 Uiso 1 1 calc R U . . .
C40 C 1.07476(16) 0.46817(11) 0.45663(4) 0.0196(2) Uani 1 1 d . . . . .
H40 H 1.183290 0.495462 0.450652 0.023 Uiso 1 1 calc R U . . .
C41 C 1.04937(17) 0.39268(12) 0.48934(4) 0.0205(2) Uani 1 1 d . . . . .
H41 H 1.140468 0.368467 0.505659 0.025 Uiso 1 1 calc R U . . .
C42 C 0.89040(18) 0.35272(12) 0.49812(4) 0.0202(2) Uani 1 1 d . . . . .
H42 H 0.872982 0.301692 0.520580 0.024 Uiso 1 1 calc R U . . .
C43 C 0.75633(15) 0.38745(11) 0.47398(3) 0.0162(2) Uani 1 1 d . . . . .
H43 H 0.647951 0.359922 0.479991 0.019 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 N12 1.8514(9) . ?
Ni1 N8 1.8583(10) . ?
Ni1 O25 1.8593(9) . ?
Ni1 N33 1.9359(10) . ?
C2 N8 1.3977(15) . ?
C2 C7 1.4193(16) . ?
C2 C3 1.4276(16) . ?
C3 C4 1.4157(16) . ?
C3 C11 1.4649(16) . ?
C4 C5 1.3795(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.393(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.3816(18) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
N8 C9 1.3681(15) . ?
C9 O10 1.2314(15) . ?
C9 C34 1.5172(17) . ?
C11 N12 1.2987(14) . ?
C11 C38 1.5033(15) . ?
N12 C13 1.4757(14) . ?
C13 C23 1.5316(16) . ?
C13 C14 1.5445(17) . ?
C13 H13 1.0000 . ?
C14 C15 1.4731(17) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.2016(18) . ?
C16 C17 1.4886(18) . ?
C17 N18 1.4603(16) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
N18 C21 1.4685(16) . ?
N18 C19 1.4699(17) . ?
C19 C20 1.521(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.5248(19) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 O24 1.2237(14) . ?
C23 O25 1.2926(14) . ?
C26 C27 1.3931(18) . ?
C26 C31 1.3965(17) . ?
C26 C32 1.5062(19) . ?
C27 C28 1.393(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.390(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.393(2) . ?
C29 H29 0.9500 . ?
C30 C31 1.386(2) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 N33 1.5043(16) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
N33 C34 1.4945(16) . ?
N33 C37 1.4974(16) . ?
C34 C35 1.5589(19) . ?
C34 H34 1.0000 . ?
C35 C36 1.529(2) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.5096(19) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 C43 1.3952(16) . ?
C38 C39 1.3987(16) . ?
C39 C40 1.3944(17) . ?
C39 H39 0.9500 . ?
C40 C41 1.3921(19) . ?
C40 H40 0.9500 . ?
C41 C42 1.392(2) . ?
C41 H41 0.9500 . ?
C42 C43 1.3974(17) . ?
C42 H42 0.9500 . ?
C43 H43 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
N12 Ni1 N8 95.00(4) . . ?
N12 Ni1 O25 86.89(4) . . ?
N8 Ni1 O25 175.83(4) . . ?
N12 Ni1 N33 176.84(4) . . ?
N8 Ni1 N33 87.59(4) . . ?
O25 Ni1 N33 90.40(4) . . ?
N8 C2 C7 121.66(11) . . ?
N8 C2 C3 121.08(10) . . ?
C7 C2 C3 117.11(10) . . ?
C4 C3 C2 119.19(10) . . ?
C4 C3 C11 116.78(10) . . ?
C2 C3 C11 124.02(10) . . ?
C5 C4 C3 122.26(12) . . ?
C5 C4 H4 118.9 . . ?
C3 C4 H4 118.9 . . ?
C4 C5 C6 118.48(12) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C7 C6 C5 121.14(11) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C2 121.79(12) . . ?
C6 C7 H7 119.1 . . ?
C2 C7 H7 119.1 . . ?
C9 N8 C2 121.53(10) . . ?
C9 N8 Ni1 113.61(8) . . ?
C2 N8 Ni1 124.58(8) . . ?
O10 C9 N8 128.04(12) . . ?
O10 C9 C34 118.41(11) . . ?
N8 C9 C34 113.50(10) . . ?
N12 C11 C3 122.39(10) . . ?
N12 C11 C38 120.06(10) . . ?
C3 C11 C38 117.47(9) . . ?
C11 N12 C13 120.70(9) . . ?
C11 N12 Ni1 127.48(8) . . ?
C13 N12 Ni1 111.25(7) . . ?
N12 C13 C23 107.49(9) . . ?
N12 C13 C14 113.04(9) . . ?
C23 C13 C14 110.55(9) . . ?
N12 C13 H13 108.5 . . ?
C23 C13 H13 108.5 . . ?
C14 C13 H13 108.5 . . ?
C15 C14 C13 115.12(10) . . ?
C15 C14 H14A 108.5 . . ?
C13 C14 H14A 108.5 . . ?
C15 C14 H14B 108.5 . . ?
C13 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
C16 C15 C14 176.68(14) . . ?
C15 C16 C17 178.64(15) . . ?
N18 C17 C16 116.58(10) . . ?
N18 C17 H17A 108.1 . . ?
C16 C17 H17A 108.1 . . ?
N18 C17 H17B 108.1 . . ?
C16 C17 H17B 108.1 . . ?
H17A C17 H17B 107.3 . . ?
C17 N18 C21 112.20(10) . . ?
C17 N18 C19 111.17(10) . . ?
C21 N18 C19 111.07(10) . . ?
N18 C19 C20 112.99(12) . . ?
N18 C19 H19A 109.0 . . ?
C20 C19 H19A 109.0 . . ?
N18 C19 H19B 109.0 . . ?
C20 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N18 C21 C22 112.64(10) . . ?
N18 C21 H21A 109.1 . . ?
C22 C21 H21A 109.1 . . ?
N18 C21 H21B 109.1 . . ?
C22 C21 H21B 109.1 . . ?
H21A C21 H21B 107.8 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O24 C23 O25 125.45(11) . . ?
O24 C23 C13 119.67(11) . . ?
O25 C23 C13 114.88(10) . . ?
C23 O25 Ni1 115.54(7) . . ?
C27 C26 C31 118.67(12) . . ?
C27 C26 C32 121.47(11) . . ?
C31 C26 C32 119.86(11) . . ?
C28 C27 C26 120.61(12) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C29 C28 C27 120.03(13) . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C28 C29 C30 119.87(14) . . ?
C28 C29 H29 120.1 . . ?
C30 C29 H29 120.1 . . ?
C31 C30 C29 119.72(13) . . ?
C31 C30 H30 120.1 . . ?
C29 C30 H30 120.1 . . ?
C30 C31 C26 121.07(13) . . ?
C30 C31 H31 119.5 . . ?
C26 C31 H31 119.5 . . ?
N33 C32 C26 113.46(10) . . ?
N33 C32 H32A 108.9 . . ?
C26 C32 H32A 108.9 . . ?
N33 C32 H32B 108.9 . . ?
C26 C32 H32B 108.9 . . ?
H32A C32 H32B 107.7 . . ?
C34 N33 C37 104.44(9) . . ?
C34 N33 C32 113.68(10) . . ?
C37 N33 C32 109.09(9) . . ?
C34 N33 Ni1 105.52(7) . . ?
C37 N33 Ni1 114.38(8) . . ?
C32 N33 Ni1 109.73(7) . . ?
N33 C34 C9 111.20(9) . . ?
N33 C34 C35 105.16(10) . . ?
C9 C34 C35 112.18(11) . . ?
N33 C34 H34 109.4 . . ?
C9 C34 H34 109.4 . . ?
C35 C34 H34 109.4 . . ?
C36 C35 C34 105.29(10) . . ?
C36 C35 H35A 110.7 . . ?
C34 C35 H35A 110.7 . . ?
C36 C35 H35B 110.7 . . ?
C34 C35 H35B 110.7 . . ?
H35A C35 H35B 108.8 . . ?
C37 C36 C35 102.94(12) . . ?
C37 C36 H36A 111.2 . . ?
C35 C36 H36A 111.2 . . ?
C37 C36 H36B 111.2 . . ?
C35 C36 H36B 111.2 . . ?
H36A C36 H36B 109.1 . . ?
N33 C37 C36 103.01(10) . . ?
N33 C37 H37A 111.2 . . ?
C36 C37 H37A 111.2 . . ?
N33 C37 H37B 111.2 . . ?
C36 C37 H37B 111.2 . . ?
H37A C37 H37B 109.1 . . ?
C43 C38 C39 119.81(11) . . ?
C43 C38 C11 121.63(11) . . ?
C39 C38 C11 118.53(10) . . ?
C40 C39 C38 119.96(11) . . ?
C40 C39 H39 120.0 . . ?
C38 C39 H39 120.0 . . ?
C41 C40 C39 120.19(12) . . ?
C41 C40 H40 119.9 . . ?
C39 C40 H40 119.9 . . ?
C42 C41 C40 119.93(12) . . ?
C42 C41 H41 120.0 . . ?
C40 C41 H41 120.0 . . ?
C41 C42 C43 120.18(12) . . ?
C41 C42 H42 119.9 . . ?
C43 C42 H42 119.9 . . ?
C38 C43 C42 119.92(12) . . ?
C38 C43 H43 120.0 . . ?
C42 C43 H43 120.0 . . ?

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
N8 C2 C3 C4 176.66(11) . . . . ?
C7 C2 C3 C4 1.10(17) . . . . ?
N8 C2 C3 C11 -2.94(17) . . . . ?
C7 C2 C3 C11 -178.50(11) . . . . ?
C2 C3 C4 C5 -1.23(19) . . . . ?
C11 C3 C4 C5 178.40(12) . . . . ?
C3 C4 C5 C6 0.1(2) . . . . ?
C4 C5 C6 C7 1.1(2) . . . . ?
C5 C6 C7 C2 -1.2(2) . . . . ?
N8 C2 C7 C6 -175.46(12) . . . . ?
C3 C2 C7 C6 0.07(18) . . . . ?
C7 C2 N8 C9 -14.60(17) . . . . ?
C3 C2 N8 C9 170.05(11) . . . . ?
C7 C2 N8 Ni1 159.00(9) . . . . ?
C3 C2 N8 Ni1 -16.36(15) . . . . ?
N12 Ni1 N8 C9 -161.31(8) . . . . ?
N33 Ni1 N8 C9 20.49(9) . . . . ?
N12 Ni1 N8 C2 24.65(10) . . . . ?
N33 Ni1 N8 C2 -153.55(10) . . . . ?
C2 N8 C9 O10 -16.58(19) . . . . ?
Ni1 N8 C9 O10 169.18(11) . . . . ?
C2 N8 C9 C34 166.07(10) . . . . ?
Ni1 N8 C9 C34 -8.17(13) . . . . ?
C4 C3 C11 N12 -173.24(11) . . . . ?
C2 C3 C11 N12 6.37(18) . . . . ?
C4 C3 C11 C38 3.45(15) . . . . ?
C2 C3 C11 C38 -176.94(11) . . . . ?
C3 C11 N12 C13 -179.05(10) . . . . ?
C38 C11 N12 C13 4.34(16) . . . . ?
C3 C11 N12 Ni1 10.41(16) . . . . ?
C38 C11 N12 Ni1 -166.20(8) . . . . ?
N8 Ni1 N12 C11 -22.20(11) . . . . ?
O25 Ni1 N12 C11 154.08(10) . . . . ?
N8 Ni1 N12 C13 166.52(8) . . . . ?
O25 Ni1 N12 C13 -17.20(8) . . . . ?
C11 N12 C13 C23 -150.99(10) . . . . ?
Ni1 N12 C13 C23 20.96(11) . . . . ?
C11 N12 C13 C14 86.72(13) . . . . ?
Ni1 N12 C13 C14 -101.33(9) . . . . ?
N12 C13 C14 C15 48.14(14) . . . . ?
C23 C13 C14 C15 -72.41(13) . . . . ?
C16 C17 N18 C21 -55.03(15) . . . . ?
C16 C17 N18 C19 70.04(15) . . . . ?
C17 N18 C19 C20 164.92(13) . . . . ?
C21 N18 C19 C20 -69.39(16) . . . . ?
C17 N18 C21 C22 -56.39(14) . . . . ?
C19 N18 C21 C22 178.49(11) . . . . ?
N12 C13 C23 O24 165.18(11) . . . . ?
C14 C13 C23 O24 -71.00(14) . . . . ?
N12 C13 C23 O25 -14.86(14) . . . . ?
C14 C13 C23 O25 108.95(12) . . . . ?
O24 C23 O25 Ni1 -178.24(11) . . . . ?
C13 C23 O25 Ni1 1.81(13) . . . . ?
N12 Ni1 O25 C23 8.91(9) . . . . ?
N33 Ni1 O25 C23 -172.72(9) . . . . ?
C31 C26 C27 C28 -0.99(19) . . . . ?
C32 C26 C27 C28 178.86(12) . . . . ?
C26 C27 C28 C29 -0.1(2) . . . . ?
C27 C28 C29 C30 0.6(2) . . . . ?
C28 C29 C30 C31 0.1(2) . . . . ?
C29 C30 C31 C26 -1.3(2) . . . . ?
C27 C26 C31 C30 1.7(2) . . . . ?
C32 C26 C31 C30 -178.15(13) . . . . ?
C27 C26 C32 N33 -92.82(14) . . . . ?
C31 C26 C32 N33 87.04(14) . . . . ?
C26 C32 N33 C34 70.00(13) . . . . ?
C26 C32 N33 C37 -173.91(10) . . . . ?
C26 C32 N33 Ni1 -47.88(12) . . . . ?
C37 N33 C34 C9 148.48(10) . . . . ?
C32 N33 C34 C9 -92.73(12) . . . . ?
Ni1 N33 C34 C9 27.56(11) . . . . ?
C37 N33 C34 C35 26.84(13) . . . . ?
C32 N33 C34 C35 145.63(11) . . . . ?
Ni1 N33 C34 C35 -94.08(10) . . . . ?
O10 C9 C34 N33 168.44(11) . . . . ?
N8 C9 C34 N33 -13.93(14) . . . . ?
O10 C9 C34 C35 -74.10(15) . . . . ?
N8 C9 C34 C35 103.53(12) . . . . ?
N33 C34 C35 C36 -1.16(15) . . . . ?
C9 C34 C35 C36 -122.17(12) . . . . ?
C34 C35 C36 C37 -24.55(15) . . . . ?
C34 N33 C37 C36 -42.97(12) . . . . ?
C32 N33 C37 C36 -164.83(10) . . . . ?
Ni1 N33 C37 C36 71.86(11) . . . . ?
C35 C36 C37 N33 41.45(13) . . . . ?
N12 C11 C38 C43 -92.29(14) . . . . ?
C3 C11 C38 C43 90.94(14) . . . . ?
N12 C11 C38 C39 89.65(14) . . . . ?
C3 C11 C38 C39 -87.12(13) . . . . ?
C43 C38 C39 C40 1.13(17) . . . . ?
C11 C38 C39 C40 179.22(11) . . . . ?
C38 C39 C40 C41 -0.79(18) . . . . ?
C39 C40 C41 C42 -0.03(19) . . . . ?
C40 C41 C42 C43 0.50(19) . . . . ?
C39 C38 C43 C42 -0.66(18) . . . . ?
C11 C38 C43 C42 -178.69(11) . . . . ?
C41 C42 C43 C38 -0.15(19) . . . . ?

_refine_diff_density_max         0.610
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.136

####################################################################### 
# 
# 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_ANNi_auto
_database_code_depnum_ccdc_archive 'CCDC 2355352'
loop_
_audit_author_name
_audit_author_address
'Armen Ayvazyan'
;Scientific Technological Center of Organic and Pharmaceutical Chemistry of NAS RA
Armenia
;
_audit_update_record             
;
2024-05-14 deposited with the CCDC.	2025-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C41 H40 N4 Ni O4'
_chemical_formula_sum            'C41 H40 N4 Ni O4'
_chemical_formula_weight         711.48

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

_cell_length_a                   9.27604(11)
_cell_length_b                   9.63867(13)
_cell_length_c                   38.6709(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3457.51(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    93875
_cell_measurement_theta_min      2.1650
_cell_measurement_theta_max      32.6980

_exptl_crystal_description       prism
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             1496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.610
_shelx_estimated_absorpt_T_min   0.784
_shelx_estimated_absorpt_T_max   0.877
_exptl_absorpt_correction_T_min  0.233
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.100a (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.
;

_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            117326
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -57
_diffrn_reflns_limit_l_max       56
_diffrn_reflns_theta_min         2.104
_diffrn_reflns_theta_max         32.425
_diffrn_reflns_theta_full        25.214
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             11424
_reflns_number_gt                11181
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.746
_reflns_Friedel_fraction_max     0.884
_reflns_Friedel_fraction_full    1.000

_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 1.171.43.92a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 (Ferrugia, 2012)'
_computing_publication_material  'enCIFer version 1.7 (Allen et al., 2004)'

_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)+(0.0347P)²+0.9433P] 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 4653 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0041(19)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         11424
_refine_ls_number_parameters     451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0265
_refine_ls_wR_factor_ref         0.0678
_refine_ls_wR_factor_gt          0.0675
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_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 0.39406(2) 0.27347(2) 0.39350(2) 0.01227(4) Uani 1 1 d . . . . .
O16 O 0.24976(13) 0.16218(12) 0.37621(3) 0.0203(2) Uani 1 1 d . . . . .
O17 O 0.02827(13) 0.16786(13) 0.35411(4) 0.0239(3) Uani 1 1 d . . . . .
N9 N 0.25549(13) 0.41177(12) 0.39836(3) 0.0112(2) Uani 1 1 d . . . . .
N30 N 0.54474(13) 0.37258(14) 0.41279(3) 0.0137(2) Uani 1 1 d . . . . .
N46 N 0.53415(15) 0.12976(15) 0.38277(4) 0.0198(3) Uani 1 1 d . . . . .
O32 O 0.79612(14) 0.37589(16) 0.41329(4) 0.0280(3) Uani 1 1 d . . . . .
N18 N 0.28874(14) 0.74523(14) 0.26723(3) 0.0168(2) Uani 1 1 d . . . . .
O21 O 0.05192(15) 0.93229(16) 0.25978(4) 0.0304(3) Uani 1 1 d . . . . .
C2 C 0.39920(17) 0.56593(14) 0.43399(3) 0.0134(2) Uani 1 1 d . . . . .
C8 C 0.27232(15) 0.53223(15) 0.41291(4) 0.0124(2) Uani 1 1 d . . . . .
C10 C 0.11751(16) 0.37404(14) 0.38096(4) 0.0122(2) Uani 1 1 d . . . . .
H10 H 0.039582 0.378500 0.398792 0.015 Uiso 1 1 calc R U . . .
C15 C 0.12897(15) 0.22322(16) 0.36906(4) 0.0156(2) Uani 1 1 d . . . . .
C13 C 0.27472(18) 0.54769(17) 0.30681(4) 0.0175(3) Uani 1 1 d . . . . .
C14 C 0.36481(17) 0.62302(16) 0.28126(4) 0.0164(3) Uani 1 1 d . . . . .
H14 H 0.382853 0.558285 0.261521 0.020 Uiso 1 1 calc R U . . .
C12 C 0.18494(18) 0.50440(16) 0.32642(4) 0.0163(3) Uani 1 1 d . . . . .
C33 C 0.16105(16) 0.64314(15) 0.40940(4) 0.0137(2) Uani 1 1 d . . . . .
C11 C 0.06963(16) 0.46475(16) 0.35026(4) 0.0144(3) Uani 1 1 d . . . . .
H11A H -0.005127 0.413912 0.337092 0.017 Uiso 1 1 calc R U . . .
H11B H 0.024574 0.550242 0.359451 0.017 Uiso 1 1 calc R U . . .
C47 C 0.67708(16) 0.20182(17) 0.38071(4) 0.0180(3) Uani 1 1 d . . . . .
H47 H 0.755788 0.135702 0.387091 0.022 Uiso 1 1 calc R U . . .
C7 C 0.38809(19) 0.68281(17) 0.45597(4) 0.0187(3) Uani 1 1 d . . . . .
H7 H 0.305843 0.741069 0.454127 0.022 Uiso 1 1 calc R U . . .
C3 C 0.52592(17) 0.48405(16) 0.43533(4) 0.0148(3) Uani 1 1 d . . . . .
C38 C 0.19446(17) 0.75585(15) 0.38810(4) 0.0171(3) Uani 1 1 d . . . . .
H38 H 0.286523 0.761367 0.377429 0.020 Uiso 1 1 calc R U . . .
C24 C 0.51153(18) 0.66598(18) 0.29560(4) 0.0195(3) Uani 1 1 d . . . . .
C31 C 0.68008(17) 0.32567(17) 0.40479(4) 0.0172(3) Uani 1 1 d . . . . .
C34 C 0.02717(18) 0.63668(17) 0.42581(4) 0.0180(3) Uani 1 1 d . . . . .
H34 H 0.004913 0.561075 0.440638 0.022 Uiso 1 1 calc R U . . .
C37 C 0.0935(2) 0.85965(16) 0.38251(4) 0.0226(3) Uani 1 1 d . . . . .
H37 H 0.115784 0.935732 0.367840 0.027 Uiso 1 1 calc R U . . .
C23 C 0.15714(18) 0.70581(18) 0.24844(4) 0.0205(3) Uani 1 1 d . . . . .
H23A H 0.088854 0.659560 0.264386 0.025 Uiso 1 1 calc R U . . .
H23B H 0.181359 0.640021 0.229660 0.025 Uiso 1 1 calc R U . . .
C48 C 0.69484(19) 0.2472(2) 0.34244(4) 0.0279(4) Uani 1 1 d . . . . .
H48A H 0.701101 0.349480 0.340583 0.033 Uiso 1 1 calc R U . . .
H48B H 0.782636 0.205817 0.332174 0.033 Uiso 1 1 calc R U . . .
C39 C 0.5586(2) 0.05717(18) 0.44542(5) 0.0242(3) Uani 1 1 d . . . . .
C6 C 0.4929(2) 0.7148(2) 0.47999(4) 0.0243(3) Uani 1 1 d . . . . .
H6 H 0.483771 0.794532 0.494273 0.029 Uiso 1 1 calc R U . . .
C35 C -0.07340(19) 0.74127(19) 0.42037(5) 0.0247(3) Uani 1 1 d . . . . .
H35 H -0.164511 0.737442 0.431553 0.030 Uiso 1 1 calc R U . . .
C4 C 0.62968(18) 0.5157(2) 0.46095(5) 0.0228(3) Uani 1 1 d . . . . .
H4 H 0.712857 0.458852 0.463183 0.027 Uiso 1 1 calc R U . . .
C36 C -0.0406(2) 0.85167(18) 0.39853(5) 0.0266(4) Uani 1 1 d . . . . .
H36 H -0.110254 0.922096 0.394532 0.032 Uiso 1 1 calc R U . . .
C5 C 0.6119(2) 0.6282(2) 0.48286(5) 0.0273(3) Uani 1 1 d . . . . .
H5 H 0.682308 0.646398 0.500116 0.033 Uiso 1 1 calc R U . . .
C40 C 0.6964(2) 0.0454(2) 0.45910(5) 0.0278(4) Uani 1 1 d . . . . .
H40 H 0.771683 0.009253 0.445104 0.033 Uiso 1 1 calc R U . . .
C29 C 0.6009(2) 0.74850(18) 0.27496(5) 0.0251(3) Uani 1 1 d . . . . .
H29 H 0.568914 0.777447 0.252768 0.030 Uiso 1 1 calc R U . . .
C22 C 0.0883(2) 0.8350(2) 0.23337(5) 0.0284(4) Uani 1 1 d . . . . .
H22A H 0.155905 0.878781 0.216846 0.034 Uiso 1 1 calc R U . . .
H22B H 0.000065 0.808758 0.220530 0.034 Uiso 1 1 calc R U . . .
C19 C 0.2507(2) 0.84544(17) 0.29415(4) 0.0218(3) Uani 1 1 d . . . . .
H19A H 0.338720 0.874487 0.306686 0.026 Uiso 1 1 calc R U . . .
H19B H 0.184327 0.801684 0.310970 0.026 Uiso 1 1 calc R U . . .
C49 C 0.5579(2) 0.1924(3) 0.32428(5) 0.0368(5) Uani 1 1 d . . . . .
H49A H 0.482213 0.264635 0.323253 0.044 Uiso 1 1 calc R U . . .
H49B H 0.579735 0.160376 0.300518 0.044 Uiso 1 1 calc R U . . .
C27 C 0.7840(2) 0.7470(2) 0.31911(6) 0.0355(5) Uani 1 1 d . . . . .
H27 H 0.876533 0.774450 0.327113 0.043 Uiso 1 1 calc R U . . .
C25 C 0.5598(2) 0.6250(2) 0.32803(5) 0.0272(4) Uani 1 1 d . . . . .
H25 H 0.499758 0.569377 0.342302 0.033 Uiso 1 1 calc R U . . .
C44 C 0.4487(2) 0.1087(2) 0.46665(6) 0.0323(4) Uani 1 1 d . . . . .
H44 H 0.353043 0.115705 0.458033 0.039 Uiso 1 1 calc R U . . .
C28 C 0.7364(2) 0.7884(2) 0.28675(6) 0.0314(4) Uani 1 1 d . . . . .
H28 H 0.796564 0.844287 0.272557 0.038 Uiso 1 1 calc R U . . .
C45 C 0.5287(2) 0.01364(18) 0.40856(6) 0.0270(4) Uani 1 1 d . . . . .
H45A H 0.600059 -0.057719 0.401783 0.032 Uiso 1 1 calc R U . . .
H45B H 0.432020 -0.029711 0.407570 0.032 Uiso 1 1 calc R U . . .
C50 C 0.5122(2) 0.0727(2) 0.34706(6) 0.0332(5) Uani 1 1 d . . . . .
H50A H 0.409945 0.047938 0.343067 0.040 Uiso 1 1 calc R U . . .
H50B H 0.573136 -0.009992 0.343033 0.040 Uiso 1 1 calc R U . . .
C20 C 0.1789(2) 0.9712(2) 0.27814(6) 0.0287(4) Uani 1 1 d . . . . .
H20A H 0.153535 1.038335 0.296540 0.034 Uiso 1 1 calc R U . . .
H20B H 0.247058 1.017194 0.262101 0.034 Uiso 1 1 calc R U . . .
C26 C 0.6960(2) 0.6650(3) 0.33984(6) 0.0354(5) Uani 1 1 d . . . . .
H26 H 0.728391 0.636253 0.362018 0.042 Uiso 1 1 calc R U . . .
C43 C 0.4794(3) 0.1496(3) 0.50039(6) 0.0399(5) Uani 1 1 d . . . . .
H43 H 0.404458 0.184674 0.514675 0.048 Uiso 1 1 calc R U . . .
C42 C 0.6182(3) 0.1395(2) 0.51328(6) 0.0415(5) Uani 1 1 d . . . . .
H42 H 0.638865 0.169666 0.536137 0.050 Uiso 1 1 calc R U . . .
C41 C 0.7263(3) 0.0855(2) 0.49287(6) 0.0355(5) Uani 1 1 d . . . . .
H41 H 0.821108 0.075788 0.501854 0.043 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 O16 1.8411(12) . ?
Ni1 N30 1.8501(13) . ?
Ni1 N9 1.8613(12) . ?
Ni1 N46 1.9441(14) . ?
O16 C15 1.2953(18) . ?
O17 C15 1.2213(18) . ?
N9 C8 1.2997(18) . ?
N9 C10 1.4910(18) . ?
N30 C31 1.3698(19) . ?
N30 C3 1.3943(19) . ?
N46 C47 1.499(2) . ?
N46 C45 1.500(3) . ?
N46 C50 1.500(2) . ?
O32 C31 1.225(2) . ?
N18 C19 1.463(2) . ?
N18 C23 1.471(2) . ?
N18 C14 1.476(2) . ?
O21 C20 1.426(3) . ?
O21 C22 1.427(3) . ?
C2 C7 1.4150(19) . ?
C2 C3 1.417(2) . ?
C2 C8 1.468(2) . ?
C8 C33 1.492(2) . ?
C10 C15 1.529(2) . ?
C10 C11 1.540(2) . ?
C10 H10 1.0000 . ?
C13 C12 1.201(2) . ?
C13 C14 1.484(2) . ?
C14 C24 1.527(2) . ?
C14 H14 1.0000 . ?
C12 C11 1.463(2) . ?
C33 C34 1.396(2) . ?
C33 C38 1.398(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C47 C31 1.514(2) . ?
C47 C48 1.552(2) . ?
C47 H47 1.0000 . ?
C7 C6 1.379(2) . ?
C7 H7 0.9500 . ?
C3 C4 1.415(2) . ?
C38 C37 1.387(2) . ?
C38 H38 0.9500 . ?
C24 C25 1.389(3) . ?
C24 C29 1.399(2) . ?
C34 C35 1.390(2) . ?
C34 H34 0.9500 . ?
C37 C36 1.392(3) . ?
C37 H37 0.9500 . ?
C23 C22 1.516(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C48 C49 1.545(3) . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C39 C40 1.388(3) . ?
C39 C44 1.400(3) . ?
C39 C45 1.512(3) . ?
C6 C5 1.389(3) . ?
C6 H6 0.9500 . ?
C35 C36 1.392(3) . ?
C35 H35 0.9500 . ?
C4 C5 1.386(2) . ?
C4 H4 0.9500 . ?
C36 H36 0.9500 . ?
C5 H5 0.9500 . ?
C40 C41 1.390(3) . ?
C40 H40 0.9500 . ?
C29 C28 1.391(3) . ?
C29 H29 0.9500 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C19 C20 1.516(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C49 C50 1.512(4) . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C27 C28 1.386(3) . ?
C27 C26 1.390(3) . ?
C27 H27 0.9500 . ?
C25 C26 1.398(3) . ?
C25 H25 0.9500 . ?
C44 C43 1.392(4) . ?
C44 H44 0.9500 . ?
C28 H28 0.9500 . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C26 H26 0.9500 . ?
C43 C42 1.384(4) . ?
C43 H43 0.9500 . ?
C42 C41 1.378(4) . ?
C42 H42 0.9500 . ?
C41 H41 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
O16 Ni1 N30 175.27(6) . . ?
O16 Ni1 N9 87.24(5) . . ?
N30 Ni1 N9 96.39(5) . . ?
O16 Ni1 N46 89.62(5) . . ?
N30 Ni1 N46 87.08(6) . . ?
N9 Ni1 N46 173.42(6) . . ?
C15 O16 Ni1 116.22(10) . . ?
C8 N9 C10 121.09(12) . . ?
C8 N9 Ni1 126.91(10) . . ?
C10 N9 Ni1 111.87(9) . . ?
C31 N30 C3 120.69(13) . . ?
C31 N30 Ni1 115.52(10) . . ?
C3 N30 Ni1 123.73(10) . . ?
C47 N46 C45 114.26(13) . . ?
C47 N46 C50 103.95(14) . . ?
C45 N46 C50 109.52(15) . . ?
C47 N46 Ni1 105.81(10) . . ?
C45 N46 Ni1 111.54(11) . . ?
C50 N46 Ni1 111.51(11) . . ?
C19 N18 C23 108.78(13) . . ?
C19 N18 C14 112.38(12) . . ?
C23 N18 C14 111.85(12) . . ?
C20 O21 C22 109.52(15) . . ?
C7 C2 C3 118.82(14) . . ?
C7 C2 C8 116.82(14) . . ?
C3 C2 C8 124.21(12) . . ?
N9 C8 C2 122.30(13) . . ?
N9 C8 C33 121.17(13) . . ?
C2 C8 C33 116.52(12) . . ?
N9 C10 C15 107.95(11) . . ?
N9 C10 C11 117.20(11) . . ?
C15 C10 C11 109.14(11) . . ?
N9 C10 H10 107.4 . . ?
C15 C10 H10 107.4 . . ?
C11 C10 H10 107.4 . . ?
O17 C15 O16 124.35(15) . . ?
O17 C15 C10 120.32(13) . . ?
O16 C15 C10 115.33(13) . . ?
C12 C13 C14 168.78(17) . . ?
N18 C14 C13 111.46(13) . . ?
N18 C14 C24 110.06(13) . . ?
C13 C14 C24 113.13(13) . . ?
N18 C14 H14 107.3 . . ?
C13 C14 H14 107.3 . . ?
C24 C14 H14 107.3 . . ?
C13 C12 C11 174.60(17) . . ?
C34 C33 C38 119.98(14) . . ?
C34 C33 C8 122.82(13) . . ?
C38 C33 C8 117.19(13) . . ?
C12 C11 C10 115.04(12) . . ?
C12 C11 H11A 108.5 . . ?
C10 C11 H11A 108.5 . . ?
C12 C11 H11B 108.5 . . ?
C10 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
N46 C47 C31 110.42(13) . . ?
N46 C47 C48 105.97(13) . . ?
C31 C47 C48 111.23(15) . . ?
N46 C47 H47 109.7 . . ?
C31 C47 H47 109.7 . . ?
C48 C47 H47 109.7 . . ?
C6 C7 C2 122.10(16) . . ?
C6 C7 H7 119.0 . . ?
C2 C7 H7 119.0 . . ?
N30 C3 C4 121.23(14) . . ?
N30 C3 C2 120.69(13) . . ?
C4 C3 C2 118.04(14) . . ?
C37 C38 C33 120.17(15) . . ?
C37 C38 H38 119.9 . . ?
C33 C38 H38 119.9 . . ?
C25 C24 C29 119.05(17) . . ?
C25 C24 C14 122.56(16) . . ?
C29 C24 C14 118.38(15) . . ?
O32 C31 N30 127.89(15) . . ?
O32 C31 C47 119.52(14) . . ?
N30 C31 C47 112.48(13) . . ?
C35 C34 C33 119.75(15) . . ?
C35 C34 H34 120.1 . . ?
C33 C34 H34 120.1 . . ?
C38 C37 C36 119.61(15) . . ?
C38 C37 H37 120.2 . . ?
C36 C37 H37 120.2 . . ?
N18 C23 C22 109.12(14) . . ?
N18 C23 H23A 109.9 . . ?
C22 C23 H23A 109.9 . . ?
N18 C23 H23B 109.9 . . ?
C22 C23 H23B 109.9 . . ?
H23A C23 H23B 108.3 . . ?
C49 C48 C47 104.47(16) . . ?
C49 C48 H48A 110.9 . . ?
C47 C48 H48A 110.9 . . ?
C49 C48 H48B 110.9 . . ?
C47 C48 H48B 110.9 . . ?
H48A C48 H48B 108.9 . . ?
C40 C39 C44 118.4(2) . . ?
C40 C39 C45 120.37(17) . . ?
C44 C39 C45 121.18(18) . . ?
C7 C6 C5 118.66(16) . . ?
C7 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C34 C35 C36 119.96(16) . . ?
C34 C35 H35 120.0 . . ?
C36 C35 H35 120.0 . . ?
C5 C4 C3 121.04(16) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C37 C36 C35 120.51(15) . . ?
C37 C36 H36 119.7 . . ?
C35 C36 H36 119.7 . . ?
C4 C5 C6 121.07(16) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C39 C40 C41 121.3(2) . . ?
C39 C40 H40 119.4 . . ?
C41 C40 H40 119.4 . . ?
C28 C29 C24 120.38(18) . . ?
C28 C29 H29 119.8 . . ?
C24 C29 H29 119.8 . . ?
O21 C22 C23 111.37(14) . . ?
O21 C22 H22A 109.4 . . ?
C23 C22 H22A 109.4 . . ?
O21 C22 H22B 109.4 . . ?
C23 C22 H22B 109.4 . . ?
H22A C22 H22B 108.0 . . ?
N18 C19 C20 110.09(15) . . ?
N18 C19 H19A 109.6 . . ?
C20 C19 H19A 109.6 . . ?
N18 C19 H19B 109.6 . . ?
C20 C19 H19B 109.6 . . ?
H19A C19 H19B 108.2 . . ?
C50 C49 C48 103.11(16) . . ?
C50 C49 H49A 111.1 . . ?
C48 C49 H49A 111.1 . . ?
C50 C49 H49B 111.1 . . ?
C48 C49 H49B 111.1 . . ?
H49A C49 H49B 109.1 . . ?
C28 C27 C26 119.83(18) . . ?
C28 C27 H27 120.1 . . ?
C26 C27 H27 120.1 . . ?
C24 C25 C26 120.54(19) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C43 C44 C39 120.1(2) . . ?
C43 C44 H44 120.0 . . ?
C39 C44 H44 120.0 . . ?
C27 C28 C29 120.26(19) . . ?
C27 C28 H28 119.9 . . ?
C29 C28 H28 119.9 . . ?
N46 C45 C39 114.44(14) . . ?
N46 C45 H45A 108.7 . . ?
C39 C45 H45A 108.7 . . ?
N46 C45 H45B 108.7 . . ?
C39 C45 H45B 108.7 . . ?
H45A C45 H45B 107.6 . . ?
N46 C50 C49 102.64(16) . . ?
N46 C50 H50A 111.2 . . ?
C49 C50 H50A 111.2 . . ?
N46 C50 H50B 111.2 . . ?
C49 C50 H50B 111.2 . . ?
H50A C50 H50B 109.2 . . ?
O21 C20 C19 110.84(16) . . ?
O21 C20 H20A 109.5 . . ?
C19 C20 H20A 109.5 . . ?
O21 C20 H20B 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 108.1 . . ?
C27 C26 C25 119.9(2) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C42 C43 C44 120.5(2) . . ?
C42 C43 H43 119.7 . . ?
C44 C43 H43 119.7 . . ?
C41 C42 C43 119.8(2) . . ?
C41 C42 H42 120.1 . . ?
C43 C42 H42 120.1 . . ?
C42 C41 C40 119.8(2) . . ?
C42 C41 H41 120.1 . . ?
C40 C41 H41 120.1 . . ?

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
N9 Ni1 O16 C15 10.94(12) . . . . ?
N46 Ni1 O16 C15 -163.27(13) . . . . ?
O16 Ni1 N9 C8 173.82(13) . . . . ?
N30 Ni1 N9 C8 -3.13(13) . . . . ?
O16 Ni1 N9 C10 -10.23(10) . . . . ?
N30 Ni1 N9 C10 172.81(9) . . . . ?
N9 Ni1 N30 C31 -160.28(12) . . . . ?
N46 Ni1 N30 C31 14.11(12) . . . . ?
N9 Ni1 N30 C3 22.58(13) . . . . ?
N46 Ni1 N30 C3 -163.04(13) . . . . ?
C10 N9 C8 C2 172.00(12) . . . . ?
Ni1 N9 C8 C2 -12.4(2) . . . . ?
C10 N9 C8 C33 -7.0(2) . . . . ?
Ni1 N9 C8 C33 168.65(10) . . . . ?
C7 C2 C8 N9 -163.03(14) . . . . ?
C3 C2 C8 N9 12.4(2) . . . . ?
C7 C2 C8 C33 15.97(19) . . . . ?
C3 C2 C8 C33 -168.56(14) . . . . ?
C8 N9 C10 C15 -175.83(12) . . . . ?
Ni1 N9 C10 C15 7.96(13) . . . . ?
C8 N9 C10 C11 60.53(18) . . . . ?
Ni1 N9 C10 C11 -115.69(11) . . . . ?
Ni1 O16 C15 O17 171.92(14) . . . . ?
Ni1 O16 C15 C10 -8.51(17) . . . . ?
N9 C10 C15 O17 179.70(14) . . . . ?
C11 C10 C15 O17 -51.91(19) . . . . ?
N9 C10 C15 O16 0.12(17) . . . . ?
C11 C10 C15 O16 128.51(14) . . . . ?
C19 N18 C14 C13 60.35(17) . . . . ?
C23 N18 C14 C13 -62.34(17) . . . . ?
C19 N18 C14 C24 -66.02(17) . . . . ?
C23 N18 C14 C24 171.29(13) . . . . ?
C12 C13 C14 N18 -1.6(9) . . . . ?
C12 C13 C14 C24 123.0(8) . . . . ?
N9 C8 C33 C34 71.3(2) . . . . ?
C2 C8 C33 C34 -107.71(16) . . . . ?
N9 C8 C33 C38 -107.52(16) . . . . ?
C2 C8 C33 C38 73.46(17) . . . . ?
N9 C10 C11 C12 41.83(18) . . . . ?
C15 C10 C11 C12 -81.21(15) . . . . ?
C45 N46 C47 C31 -92.46(17) . . . . ?
C50 N46 C47 C31 148.23(15) . . . . ?
Ni1 N46 C47 C31 30.65(15) . . . . ?
C45 N46 C47 C48 146.98(15) . . . . ?
C50 N46 C47 C48 27.66(17) . . . . ?
Ni1 N46 C47 C48 -89.92(13) . . . . ?
C3 C2 C7 C6 -3.8(2) . . . . ?
C8 C2 C7 C6 171.94(16) . . . . ?
C31 N30 C3 C4 -26.4(2) . . . . ?
Ni1 N30 C3 C4 150.64(14) . . . . ?
C31 N30 C3 C2 155.99(15) . . . . ?
Ni1 N30 C3 C2 -27.0(2) . . . . ?
C7 C2 C3 N30 -176.43(14) . . . . ?
C8 C2 C3 N30 8.2(2) . . . . ?
C7 C2 C3 C4 5.9(2) . . . . ?
C8 C2 C3 C4 -169.53(15) . . . . ?
C34 C33 C38 C37 -1.6(2) . . . . ?
C8 C33 C38 C37 177.22(14) . . . . ?
N18 C14 C24 C25 131.83(17) . . . . ?
C13 C14 C24 C25 6.4(2) . . . . ?
N18 C14 C24 C29 -48.93(19) . . . . ?
C13 C14 C24 C29 -174.35(15) . . . . ?
C3 N30 C31 O32 -5.5(3) . . . . ?
Ni1 N30 C31 O32 177.26(16) . . . . ?
C3 N30 C31 C47 178.49(14) . . . . ?
Ni1 N30 C31 C47 1.25(18) . . . . ?
N46 C47 C31 O32 161.66(16) . . . . ?
C48 C47 C31 O32 -81.0(2) . . . . ?
N46 C47 C31 N30 -21.95(19) . . . . ?
C48 C47 C31 N30 95.41(16) . . . . ?
C38 C33 C34 C35 1.2(2) . . . . ?
C8 C33 C34 C35 -177.62(15) . . . . ?
C33 C38 C37 C36 0.7(2) . . . . ?
C19 N18 C23 C22 57.86(17) . . . . ?
C14 N18 C23 C22 -177.42(13) . . . . ?
N46 C47 C48 C49 -1.65(18) . . . . ?
C31 C47 C48 C49 -121.69(16) . . . . ?
C2 C7 C6 C5 -0.8(3) . . . . ?
C33 C34 C35 C36 0.2(3) . . . . ?
N30 C3 C4 C5 178.72(17) . . . . ?
C2 C3 C4 C5 -3.6(3) . . . . ?
C38 C37 C36 C35 0.7(3) . . . . ?
C34 C35 C36 C37 -1.2(3) . . . . ?
C3 C4 C5 C6 -1.0(3) . . . . ?
C7 C6 C5 C4 3.3(3) . . . . ?
C44 C39 C40 C41 -1.0(3) . . . . ?
C45 C39 C40 C41 179.65(18) . . . . ?
C25 C24 C29 C28 0.2(3) . . . . ?
C14 C24 C29 C28 -179.03(16) . . . . ?
C20 O21 C22 C23 59.5(2) . . . . ?
N18 C23 C22 O21 -59.50(19) . . . . ?
C23 N18 C19 C20 -58.06(18) . . . . ?
C14 N18 C19 C20 177.54(14) . . . . ?
C47 C48 C49 C50 -24.64(19) . . . . ?
C29 C24 C25 C26 -0.3(3) . . . . ?
C14 C24 C25 C26 178.92(18) . . . . ?
C40 C39 C44 C43 1.4(3) . . . . ?
C45 C39 C44 C43 -179.25(18) . . . . ?
C26 C27 C28 C29 0.1(3) . . . . ?
C24 C29 C28 C27 -0.1(3) . . . . ?
C47 N46 C45 C39 60.33(19) . . . . ?
C50 N46 C45 C39 176.46(15) . . . . ?
Ni1 N46 C45 C39 -59.62(17) . . . . ?
C40 C39 C45 N46 -95.4(2) . . . . ?
C44 C39 C45 N46 85.3(2) . . . . ?
C47 N46 C50 C49 -43.63(16) . . . . ?
C45 N46 C50 C49 -166.13(14) . . . . ?
Ni1 N46 C50 C49 69.93(15) . . . . ?
C48 C49 C50 N46 42.07(18) . . . . ?
C22 O21 C20 C19 -58.8(2) . . . . ?
N18 C19 C20 O21 59.1(2) . . . . ?
C28 C27 C26 C25 -0.2(3) . . . . ?
C24 C25 C26 C27 0.3(3) . . . . ?
C39 C44 C43 C42 -0.2(3) . . . . ?
C44 C43 C42 C41 -1.5(3) . . . . ?
C43 C42 C41 C40 1.9(3) . . . . ?
C39 C40 C41 C42 -0.7(3) . . . . ?

_refine_diff_density_max         0.467
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.049

