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

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2201251'
loop_
_audit_author_name
_audit_author_address
'Mukesh Choudhary'
;NIT Patna
India
;
_audit_update_record             
;
2022-08-13 deposited with the CCDC.	2024-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 N2 Ni O2'
_chemical_formula_weight         425.11

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

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

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

_cell_length_a                   17.8664(14)
_cell_length_b                   8.2689(5)
_cell_length_c                   13.0861(8)
_cell_angle_alpha                90
_cell_angle_beta                 99.896(6)
_cell_angle_gamma                90
_cell_volume                     1904.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8857
_cell_measurement_theta_min      3.4890
_cell_measurement_theta_max      28.5850

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    1.042
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.64586
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16853
_diffrn_reflns_av_unetI/netI     0.0577
_diffrn_reflns_av_R_equivalents  0.1079
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.246
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             3299
_reflns_number_gt                2894
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0662P)²+2.1734P] 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         3299
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1400
_refine_ls_wR_factor_gt          0.1163
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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
C1 C 0.62286(19) 0.5774(4) 0.3799(2) 0.0337(7) Uani 1 1 d . . . . .
C2 C 0.6643(2) 0.6665(4) 0.4647(3) 0.0329(7) Uani 1 1 d . . . . .
C3 C 0.7470(2) 0.6730(4) 0.4798(3) 0.0381(8) Uani 1 1 d . . . . .
C4 C 0.7926(2) 0.7656(5) 0.5597(3) 0.0530(10) Uani 1 1 d . . . . .
H4 H 0.769195 0.828876 0.603763 0.064 Uiso 1 1 calc R U . . .
C5 C 0.8714(3) 0.7622(6) 0.5722(4) 0.0674(13) Uani 1 1 d . . . . .
H5 H 0.899828 0.822868 0.624909 0.081 Uiso 1 1 calc R U . . .
C6 C 0.9089(3) 0.6697(6) 0.5073(5) 0.0737(15) Uani 1 1 d . . . . .
H6 H 0.961701 0.667742 0.517357 0.088 Uiso 1 1 calc R U . . .
C7 C 0.8671(2) 0.5818(6) 0.4288(4) 0.0641(12) Uani 1 1 d . . . . .
H7 H 0.892070 0.520677 0.385311 0.077 Uiso 1 1 calc R U . . .
C8 C 0.7866(2) 0.5824(5) 0.4126(3) 0.0460(9) Uani 1 1 d . . . . .
C9 C 0.7425(2) 0.4895(5) 0.3301(3) 0.0479(9) Uani 1 1 d . . . . .
H9 H 0.767585 0.429074 0.286485 0.058 Uiso 1 1 calc R U . . .
C10 C 0.6644(2) 0.4879(4) 0.3144(3) 0.0410(8) Uani 1 1 d . . . . .
H10 H 0.637997 0.427384 0.259950 0.049 Uiso 1 1 calc R U . . .
C11 C 0.6247(2) 0.7355(4) 0.5403(2) 0.0358(7) Uani 1 1 d . . . . .
H11 H 0.654005 0.780719 0.598967 0.043 Uiso 1 1 calc R U . . .
C12 C 0.5180(2) 0.7955(4) 0.6260(3) 0.0417(8) Uani 1 1 d . . . . .
H12A H 0.550471 0.877040 0.664217 0.050 Uiso 1 1 calc R U . . .
H12B H 0.513949 0.705105 0.671967 0.050 Uiso 1 1 calc R U . . .
C13 C 0.4402(2) 0.8652(4) 0.5858(3) 0.0412(8) Uani 1 1 d . . . . .
H13A H 0.408409 0.858777 0.638797 0.049 Uiso 1 1 calc R U . . .
H13B H 0.444457 0.977767 0.566766 0.049 Uiso 1 1 calc R U . . .
C14 C 0.3326(2) 0.7668(4) 0.4669(2) 0.0361(7) Uani 1 1 d . . . . .
H14 H 0.305190 0.825848 0.508413 0.043 Uiso 1 1 calc R U . . .
C15 C 0.2891(2) 0.6818(4) 0.3790(3) 0.0336(7) Uani 1 1 d . . . . .
C16 C 0.2065(2) 0.6910(4) 0.3579(3) 0.0399(8) Uani 1 1 d . . . . .
C17 C 0.1634(2) 0.7848(5) 0.4174(3) 0.0530(10) Uani 1 1 d . . . . .
H17 H 0.188472 0.841247 0.474695 0.064 Uiso 1 1 calc R U . . .
C18 C 0.0849(3) 0.7946(6) 0.3925(4) 0.0683(12) Uani 1 1 d . . . . .
H18 H 0.058239 0.857194 0.433227 0.082 Uiso 1 1 calc R U . . .
C19 C 0.0450(3) 0.7107(7) 0.3061(4) 0.0754(14) Uani 1 1 d . . . . .
H19 H -0.007552 0.718633 0.288965 0.091 Uiso 1 1 calc R U . . .
C20 C 0.0852(2) 0.6168(6) 0.2475(4) 0.0636(12) Uani 1 1 d . . . . .
H20 H 0.058879 0.559744 0.191339 0.076 Uiso 1 1 calc R U . . .
C21 C 0.1659(2) 0.6045(5) 0.2704(3) 0.0466(9) Uani 1 1 d . . . . .
C22 C 0.2068(2) 0.5060(5) 0.2100(3) 0.0494(9) Uani 1 1 d . . . . .
H22 H 0.180049 0.445944 0.155596 0.059 Uiso 1 1 calc R U . . .
C23 C 0.2845(2) 0.4973(4) 0.2298(3) 0.0424(8) Uani 1 1 d . . . . .
H23 H 0.309253 0.431191 0.188686 0.051 Uiso 1 1 calc R U . . .
C24 C 0.32905(18) 0.5891(4) 0.3136(2) 0.0323(7) Uani 1 1 d . . . . .
N1 N 0.40648(15) 0.7680(3) 0.49325(19) 0.0321(6) Uani 1 1 d . . . . .
N2 N 0.55029(16) 0.7409(3) 0.53430(19) 0.0336(6) Uani 1 1 d . . . . .
Ni1 Ni 0.47707(2) 0.66527(4) 0.42697(3) 0.02959(18) Uani 1 1 d . . . . .
O1 O 0.54817(13) 0.5670(3) 0.35869(16) 0.0345(5) Uani 1 1 d . . . . .
O2 O 0.40367(13) 0.5793(3) 0.32315(16) 0.0364(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.318(4) . ?
C1 C2 1.428(4) . ?
C1 C10 1.433(5) . ?
C2 C11 1.431(5) . ?
C2 C3 1.458(5) . ?
C3 C8 1.430(5) . ?
C3 C4 1.432(5) . ?
C4 C5 1.389(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.370(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.419(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.444(5) . ?
C9 C10 1.374(5) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 N2 1.318(4) . ?
C11 H11 0.9300 . ?
C12 N2 1.488(4) . ?
C12 C13 1.513(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 N1 1.492(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N1 1.305(4) . ?
C14 C15 1.454(5) . ?
C14 H14 0.9300 . ?
C15 C24 1.428(5) . ?
C15 C16 1.458(5) . ?
C16 C17 1.416(6) . ?
C16 C21 1.436(5) . ?
C17 C18 1.387(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.412(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.376(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.426(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.421(6) . ?
C22 C23 1.370(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.454(4) . ?
C23 H23 0.9300 . ?
C24 O2 1.320(4) . ?
N1 Ni1 1.855(3) . ?
N2 Ni1 1.856(3) . ?
Ni1 O2 1.860(2) . ?
Ni1 O1 1.861(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 124.6(3) . . ?
O1 C1 C10 116.8(3) . . ?
C2 C1 C10 118.6(3) . . ?
C1 C2 C11 119.4(3) . . ?
C1 C2 C3 120.2(3) . . ?
C11 C2 C3 120.1(3) . . ?
C8 C3 C4 116.7(4) . . ?
C8 C3 C2 119.6(3) . . ?
C4 C3 C2 123.7(4) . . ?
C5 C4 C3 120.9(4) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 121.4(4) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C7 C6 C5 119.4(4) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C6 C7 C8 121.2(5) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C7 C8 C3 120.4(4) . . ?
C7 C8 C9 121.3(4) . . ?
C3 C8 C9 118.3(3) . . ?
C10 C9 C8 121.8(3) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
C9 C10 C1 121.5(3) . . ?
C9 C10 H10 119.3 . . ?
C1 C10 H10 119.3 . . ?
N2 C11 C2 125.8(3) . . ?
N2 C11 H11 117.1 . . ?
C2 C11 H11 117.1 . . ?
N2 C12 C13 107.2(3) . . ?
N2 C12 H12A 110.3 . . ?
C13 C12 H12A 110.3 . . ?
N2 C12 H12B 110.3 . . ?
C13 C12 H12B 110.3 . . ?
H12A C12 H12B 108.5 . . ?
N1 C13 C12 107.2(3) . . ?
N1 C13 H13A 110.3 . . ?
C12 C13 H13A 110.3 . . ?
N1 C13 H13B 110.3 . . ?
C12 C13 H13B 110.3 . . ?
H13A C13 H13B 108.5 . . ?
N1 C14 C15 126.2(3) . . ?
N1 C14 H14 116.9 . . ?
C15 C14 H14 116.9 . . ?
C24 C15 C14 118.7(3) . . ?
C24 C15 C16 120.6(3) . . ?
C14 C15 C16 120.7(3) . . ?
C17 C16 C21 117.7(3) . . ?
C17 C16 C15 123.6(3) . . ?
C21 C16 C15 118.7(3) . . ?
C18 C17 C16 121.7(4) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C17 C18 C19 120.6(4) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C20 C19 C18 119.0(4) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C19 C20 C21 121.9(4) . . ?
C19 C20 H20 119.0 . . ?
C21 C20 H20 119.0 . . ?
C22 C21 C20 121.5(4) . . ?
C22 C21 C16 119.5(3) . . ?
C20 C21 C16 119.0(4) . . ?
C23 C22 C21 121.8(3) . . ?
C23 C22 H22 119.1 . . ?
C21 C22 H22 119.1 . . ?
C22 C23 C24 121.4(3) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
O2 C24 C15 125.2(3) . . ?
O2 C24 C23 116.9(3) . . ?
C15 C24 C23 117.9(3) . . ?
C14 N1 C13 117.9(3) . . ?
C14 N1 Ni1 127.6(2) . . ?
C13 N1 Ni1 114.5(2) . . ?
C11 N2 C12 119.2(3) . . ?
C11 N2 Ni1 127.3(2) . . ?
C12 N2 Ni1 113.1(2) . . ?
N1 Ni1 N2 86.52(12) . . ?
N1 Ni1 O2 93.78(11) . . ?
N2 Ni1 O2 177.00(10) . . ?
N1 Ni1 O1 178.54(10) . . ?
N2 Ni1 O1 93.43(11) . . ?
O2 Ni1 O1 86.34(10) . . ?
C1 O1 Ni1 128.34(19) . . ?
C24 O2 Ni1 128.3(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
O1 C1 C2 C11 7.6(4) . . . . ?
C10 C1 C2 C11 -170.3(3) . . . . ?
O1 C1 C2 C3 -178.6(3) . . . . ?
C10 C1 C2 C3 3.6(4) . . . . ?
C1 C2 C3 C8 -3.4(4) . . . . ?
C11 C2 C3 C8 170.3(3) . . . . ?
C1 C2 C3 C4 176.9(3) . . . . ?
C11 C2 C3 C4 -9.3(5) . . . . ?
C8 C3 C4 C5 -1.9(5) . . . . ?
C2 C3 C4 C5 177.7(3) . . . . ?
C3 C4 C5 C6 0.4(7) . . . . ?
C4 C5 C6 C7 0.8(7) . . . . ?
C5 C6 C7 C8 -0.4(7) . . . . ?
C6 C7 C8 C3 -1.2(6) . . . . ?
C6 C7 C8 C9 -179.8(4) . . . . ?
C4 C3 C8 C7 2.3(5) . . . . ?
C2 C3 C8 C7 -177.4(3) . . . . ?
C4 C3 C8 C9 -179.0(3) . . . . ?
C2 C3 C8 C9 1.3(5) . . . . ?
C7 C8 C9 C10 179.4(4) . . . . ?
C3 C8 C9 C10 0.8(5) . . . . ?
C8 C9 C10 C1 -0.6(5) . . . . ?
O1 C1 C10 C9 -179.6(3) . . . . ?
C2 C1 C10 C9 -1.5(5) . . . . ?
C1 C2 C11 N2 -8.0(5) . . . . ?
C3 C2 C11 N2 178.2(3) . . . . ?
N2 C12 C13 N1 35.0(4) . . . . ?
N1 C14 C15 C24 0.3(5) . . . . ?
N1 C14 C15 C16 -179.8(3) . . . . ?
C24 C15 C16 C17 -177.8(3) . . . . ?
C14 C15 C16 C17 2.2(5) . . . . ?
C24 C15 C16 C21 0.2(5) . . . . ?
C14 C15 C16 C21 -179.7(3) . . . . ?
C21 C16 C17 C18 -0.4(6) . . . . ?
C15 C16 C17 C18 177.7(4) . . . . ?
C16 C17 C18 C19 -0.1(8) . . . . ?
C17 C18 C19 C20 0.9(8) . . . . ?
C18 C19 C20 C21 -1.3(8) . . . . ?
C19 C20 C21 C22 179.4(4) . . . . ?
C19 C20 C21 C16 0.8(7) . . . . ?
C17 C16 C21 C22 -178.6(3) . . . . ?
C15 C16 C21 C22 3.2(5) . . . . ?
C17 C16 C21 C20 0.0(5) . . . . ?
C15 C16 C21 C20 -178.1(3) . . . . ?
C20 C21 C22 C23 178.1(4) . . . . ?
C16 C21 C22 C23 -3.3(5) . . . . ?
C21 C22 C23 C24 -0.2(5) . . . . ?
C14 C15 C24 O2 -3.4(5) . . . . ?
C16 C15 C24 O2 176.7(3) . . . . ?
C14 C15 C24 C23 176.4(3) . . . . ?
C16 C15 C24 C23 -3.6(4) . . . . ?
C22 C23 C24 O2 -176.6(3) . . . . ?
C22 C23 C24 C15 3.6(5) . . . . ?
C15 C14 N1 C13 179.1(3) . . . . ?
C15 C14 N1 Ni1 0.6(5) . . . . ?
C12 C13 N1 C14 157.0(3) . . . . ?
C12 C13 N1 Ni1 -24.3(3) . . . . ?
C2 C11 N2 C12 171.3(3) . . . . ?
C2 C11 N2 Ni1 -1.2(5) . . . . ?
C13 C12 N2 C11 153.4(3) . . . . ?
C13 C12 N2 Ni1 -33.0(3) . . . . ?
C14 N1 Ni1 N2 -176.3(3) . . . . ?
C13 N1 Ni1 N2 5.2(2) . . . . ?
C14 N1 Ni1 O2 0.7(3) . . . . ?
C13 N1 Ni1 O2 -177.8(2) . . . . ?
C11 N2 Ni1 N1 -170.7(3) . . . . ?
C12 N2 Ni1 N1 16.3(2) . . . . ?
C11 N2 Ni1 O1 7.8(3) . . . . ?
C12 N2 Ni1 O1 -165.1(2) . . . . ?
C2 C1 O1 Ni1 1.9(4) . . . . ?
C10 C1 O1 Ni1 179.8(2) . . . . ?
N2 Ni1 O1 C1 -8.2(2) . . . . ?
O2 Ni1 O1 C1 174.8(2) . . . . ?
C15 C24 O2 Ni1 5.5(4) . . . . ?
C23 C24 O2 Ni1 -174.3(2) . . . . ?
N1 Ni1 O2 C24 -3.7(3) . . . . ?
O1 Ni1 O2 C24 177.7(3) . . . . ?

_refine_diff_density_max         0.565
_refine_diff_density_min         -0.753
_refine_diff_density_rms         0.090

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2201252'
loop_
_audit_author_name
_audit_author_address
'Mukesh Choudhary'
;NIT Patna
India
;
_audit_update_record             
;
2022-08-13 deposited with the CCDC.	2024-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 N2 Ni O2'
_chemical_formula_weight         425.11

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.243(4)
_cell_length_b                   13.068(3)
_cell_length_c                   17.906(5)
_cell_angle_alpha                99.85(2)
_cell_angle_beta                 92.64(8)
_cell_angle_gamma                93.66(7)
_cell_volume                     1893.3(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2317
_cell_measurement_theta_min      3.025
_cell_measurement_theta_max      24.997

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    1.048
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.871
_exptl_absorpt_correction_T_max  0.910
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16465
_diffrn_reflns_av_unetI/netI     0.0834
_diffrn_reflns_av_R_equivalents  0.0936
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.025
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             6639
_reflns_number_gt                4892
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0527P)²+0.2766P] 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         6639
_refine_ls_number_parameters     523
_refine_ls_number_restraints     420
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1276
_refine_ls_wR_factor_gt          0.1046
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.129
_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
C1 C 0.5894(4) 0.1862(2) 0.6713(2) 0.0349(7) Uani 1 1 d . U . . .
C2 C 0.6819(4) 0.1213(2) 0.7103(2) 0.0343(7) Uani 1 1 d . U . . .
C3 C 0.6914(4) 0.1424(3) 0.7938(2) 0.0425(7) Uani 1 1 d . U . . .
C4 C 0.7847(5) 0.0825(3) 0.8367(2) 0.0539(9) Uani 1 1 d . U . . .
H4 H 0.838491 0.026894 0.812421 0.065 Uiso 1 1 calc R U . . .
C5 C 0.7945(5) 0.1081(4) 0.9154(2) 0.0646(10) Uani 1 1 d . U . . .
H5 H 0.856571 0.069453 0.943450 0.078 Uiso 1 1 calc R U . . .
C6 C 0.7103(6) 0.1937(4) 0.9548(3) 0.0703(11) Uani 1 1 d . U . . .
H6 H 0.719466 0.208843 1.007579 0.084 Uiso 1 1 calc R U . . .
C7 C 0.6168(5) 0.2529(3) 0.9155(2) 0.0613(10) Uani 1 1 d . U . . .
H7 H 0.562198 0.307016 0.941276 0.074 Uiso 1 1 calc R U . . .
C8 C 0.6052(4) 0.2295(3) 0.8340(2) 0.0464(8) Uani 1 1 d . U . . .
C9 C 0.5059(4) 0.2895(3) 0.7930(2) 0.0477(8) Uani 1 1 d . U . . .
H9 H 0.447095 0.341351 0.818983 0.057 Uiso 1 1 calc R U . . .
C10 C 0.4980(4) 0.2701(3) 0.7157(2) 0.0411(8) Uani 1 1 d . U . . .
H10 H 0.434070 0.309958 0.689452 0.049 Uiso 1 1 calc R U . . .
C11 C 0.7664(4) 0.0333(2) 0.6676(2) 0.0356(7) Uani 1 1 d . U . . .
H11 H 0.823563 -0.006672 0.696583 0.043 Uiso 1 1 calc R U . . .
C12 C 0.8647(4) -0.0858(2) 0.5592(2) 0.0386(7) Uani 1 1 d . U . . .
H12A H 0.978738 -0.063100 0.558101 0.046 Uiso 1 1 calc R U . . .
H12B H 0.856393 -0.140165 0.589910 0.046 Uiso 1 1 calc R U . . .
C13 C 0.7957(4) -0.1263(2) 0.4813(2) 0.0386(7) Uani 1 1 d . U . . .
H13A H 0.704554 -0.176702 0.482138 0.046 Uiso 1 1 calc R U . . .
H13B H 0.877583 -0.159791 0.450442 0.046 Uiso 1 1 calc R U . . .
C14 C 0.7365(4) -0.0406(2) 0.3758(2) 0.0350(7) Uani 1 1 d . U . . .
H14 H 0.780867 -0.097126 0.347252 0.042 Uiso 1 1 calc R U . . .
C15 C 0.6673(4) 0.0349(2) 0.33627(19) 0.0338(7) Uani 1 1 d . U . . .
C16 C 0.6734(4) 0.0201(3) 0.2526(2) 0.0400(7) Uani 1 1 d . U . . .
C17 C 0.7659(5) -0.0592(3) 0.2076(2) 0.0520(9) Uani 1 1 d . U . . .
H17 H 0.827883 -0.101409 0.232553 0.062 Uiso 1 1 calc R U . . .
C18 C 0.7627(5) -0.0724(4) 0.1285(2) 0.0636(10) Uani 1 1 d . U . . .
H18 H 0.821217 -0.123014 0.100905 0.076 Uiso 1 1 calc R U . . .
C19 C 0.6696(6) -0.0079(4) 0.0914(3) 0.0685(11) Uani 1 1 d . U . . .
H19 H 0.665099 -0.017105 0.038687 0.082 Uiso 1 1 calc R U . . .
C20 C 0.5817(5) 0.0716(4) 0.1328(2) 0.0608(10) Uani 1 1 d . U . . .
H20 H 0.523098 0.114048 0.106524 0.073 Uiso 1 1 calc R U . . .
C21 C 0.4899(4) 0.1698(3) 0.2575(2) 0.0480(8) Uani 1 1 d . U . . .
H21 H 0.431342 0.212119 0.231077 0.058 Uiso 1 1 calc R U . . .
C22 C 0.4880(4) 0.1859(3) 0.3352(2) 0.0420(8) Uani 1 1 d . U . . .
H22 H 0.430074 0.238577 0.360685 0.050 Uiso 1 1 calc R U . . .
C23 C 0.5776(4) 0.1196(2) 0.3772(2) 0.0351(7) Uani 1 1 d . U . . .
C24 C 0.9112(4) 0.6859(2) 0.6715(2) 0.0349(7) Uani 1 1 d . U . . .
C25 C 0.8180(4) 0.6212(2) 0.7102(2) 0.0337(7) Uani 1 1 d . U . . .
C26 C 0.8084(4) 0.6423(3) 0.7938(2) 0.0405(7) Uani 1 1 d . U . . .
C27 C 0.7150(5) 0.5826(3) 0.8366(2) 0.0535(9) Uani 1 1 d . U . . .
H27 H 0.655523 0.522977 0.811104 0.064 Uiso 1 1 calc R U . . .
C28 C 0.7061(5) 0.6075(4) 0.9153(2) 0.0658(10) Uani 1 1 d . U . . .
H28 H 0.642421 0.564660 0.940623 0.079 Uiso 1 1 calc R U . . .
C29 C 0.7899(6) 0.6939(4) 0.9549(3) 0.0704(11) Uani 1 1 d . U . . .
H29 H 0.784083 0.712217 1.007164 0.084 Uiso 1 1 calc R U . . .
C30 C 0.8828(5) 0.7526(4) 0.9151(2) 0.0616(10) Uani 1 1 d . U . . .
H30 H 0.941794 0.811613 0.941810 0.074 Uiso 1 1 calc R U . . .
C31 C 0.8956(4) 0.7292(3) 0.8345(2) 0.0460(8) Uani 1 1 d . U . . .
C32 C 0.9940(4) 0.7901(3) 0.7930(2) 0.0484(8) Uani 1 1 d . U . . .
H32 H 1.057023 0.847232 0.820019 0.058 Uiso 1 1 calc R U . . .
C33 C 0.7338(4) 0.5333(2) 0.6678(2) 0.0347(7) Uani 1 1 d . U . . .
H33 H 0.673638 0.489811 0.694024 0.042 Uiso 1 1 calc R U . . .
C34 C 0.6358(4) 0.4137(2) 0.5591(2) 0.0403(8) Uani 1 1 d . U . . .
H34A H 0.522894 0.428886 0.552350 0.048 Uiso 1 1 calc R U . . .
H34B H 0.641227 0.361317 0.591324 0.048 Uiso 1 1 calc R U . . .
C35 C 0.7034(4) 0.3736(2) 0.4815(2) 0.0395(7) Uani 1 1 d . U . . .
H35A H 0.793413 0.330822 0.487758 0.047 Uiso 1 1 calc R U . . .
H35B H 0.619296 0.331924 0.447913 0.047 Uiso 1 1 calc R U . . .
C36 C 0.7642(4) 0.4596(2) 0.3759(2) 0.0354(7) Uani 1 1 d . U . . .
H36 H 0.716937 0.398652 0.346268 0.042 Uiso 1 1 calc R U . . .
C37 C 0.8335(4) 0.5353(2) 0.3365(2) 0.0332(7) Uani 1 1 d . U . . .
C38 C 0.8268(4) 0.5198(3) 0.2523(2) 0.0393(7) Uani 1 1 d . U . . .
C39 C 0.7340(5) 0.4404(3) 0.2076(2) 0.0515(9) Uani 1 1 d . U . . .
H39 H 0.667976 0.395038 0.229800 0.062 Uiso 1 1 calc R U . . .
C40 C 0.7374(6) 0.4268(4) 0.1286(2) 0.0639(10) Uani 1 1 d . U . . .
H40 H 0.674410 0.371185 0.099689 0.077 Uiso 1 1 calc R U . . .
C41 C 0.8306(6) 0.4925(4) 0.0911(3) 0.0686(11) Uani 1 1 d . U . . .
H41 H 0.830691 0.480893 0.038422 0.082 Uiso 1 1 calc R U . . .
C42 C 0.9184(5) 0.5716(4) 0.1324(2) 0.0594(9) Uani 1 1 d . U . . .
H42 H 0.981036 0.617289 0.108985 0.071 Uiso 1 1 calc R U . . .
C43 C 0.9173(4) 0.5872(3) 0.2139(2) 0.0458(8) Uani 1 1 d . U . . .
C44 C 1.0104(4) 0.6699(3) 0.2578(2) 0.0466(8) Uani 1 1 d . U . . .
H44 H 1.072490 0.715447 0.234061 0.056 Uiso 1 1 calc R U . . .
C45 C 1.0129(4) 0.6856(3) 0.3349(2) 0.0404(8) Uani 1 1 d . U . . .
H45 H 1.076958 0.742332 0.361851 0.049 Uiso 1 1 calc R U . . .
C46 C 0.9224(4) 0.6200(2) 0.3772(2) 0.0337(7) Uani 1 1 d . U . . .
C47 C 0.5819(4) 0.0875(3) 0.2138(2) 0.0475(8) Uani 1 1 d . U . . .
C48 C 1.0022(4) 0.7701(3) 0.7152(2) 0.0422(8) Uani 1 1 d . U . . .
H00O H 1.069209 0.813371 0.691756 0.051 Uiso 1 1 calc R U . . .
N1 N 0.7406(3) -0.03428(19) 0.44954(16) 0.0322(6) Uani 1 1 d . U . . .
N2 N 0.7681(3) 0.00681(19) 0.59372(16) 0.0329(6) Uani 1 1 d . U . . .
N3 N 0.7324(3) 0.50665(19) 0.59358(16) 0.0318(6) Uani 1 1 d . U . . .
N4 N 0.7593(3) 0.46603(19) 0.44969(16) 0.0321(6) Uani 1 1 d . U . . .
O1 O 0.5666(3) 0.14136(15) 0.45175(13) 0.0345(5) Uani 1 1 d . U . . .
O2 O 0.5791(3) 0.17709(16) 0.59674(13) 0.0361(5) Uani 1 1 d . U . . .
O3 O 0.9210(3) 0.67665(16) 0.59681(13) 0.0356(5) Uani 1 1 d . U . . .
O4 O 0.9332(3) 0.64150(15) 0.45189(13) 0.0345(5) Uani 1 1 d . U . . .
Ni1 Ni 0.66524(5) 0.07302(3) 0.52297(2) 0.02958(14) Uani 1 1 d . U . . .
Ni2 Ni 0.83485(5) 0.57305(3) 0.52294(2) 0.02946(14) Uani 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.318(4) . ?
C1 C2 1.422(5) . ?
C1 C10 1.504(5) . ?
C2 C3 1.472(5) . ?
C2 C11 1.497(5) . ?
C3 C4 1.423(5) . ?
C3 C8 1.480(5) . ?
C4 C5 1.388(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.452(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.379(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.436(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.430(5) . ?
C9 C10 1.363(5) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 N2 1.311(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.479(5) . ?
C12 N2 1.547(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 N1 1.501(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N1 1.307(4) . ?
C14 C15 1.440(5) . ?
C14 H14 0.9300 . ?
C15 C23 1.478(5) . ?
C15 C16 1.481(5) . ?
C16 C47 1.440(5) . ?
C16 C17 1.475(5) . ?
C17 C18 1.396(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.403(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.427(6) . ?
C19 H19 0.9300 . ?
C20 C47 1.428(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.372(5) . ?
C21 C47 1.489(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.455(5) . ?
C22 H22 0.9300 . ?
C23 O1 1.325(4) . ?
C24 O3 1.328(4) . ?
C24 C48 1.390(5) . ?
C24 C25 1.397(5) . ?
C25 C33 1.389(5) . ?
C25 C26 1.481(5) . ?
C26 C31 1.379(5) . ?
C26 C27 1.405(5) . ?
C27 C28 1.398(6) . ?
C27 H27 0.9300 . ?
C28 C29 1.354(6) . ?
C28 H28 0.9300 . ?
C29 C30 1.358(6) . ?
C29 H29 0.9300 . ?
C30 C31 1.433(5) . ?
C30 H30 0.9300 . ?
C31 C32 1.422(5) . ?
C32 C48 1.377(5) . ?
C32 H32 0.9300 . ?
C33 N3 1.315(4) . ?
C33 H33 0.9300 . ?
C34 N3 1.437(4) . ?
C34 C35 1.541(5) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 N4 1.479(4) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 N4 1.311(4) . ?
C36 C37 1.417(5) . ?
C36 H36 0.9300 . ?
C37 C46 1.365(4) . ?
C37 C38 1.484(5) . ?
C38 C39 1.364(5) . ?
C38 C43 1.407(5) . ?
C39 C40 1.396(6) . ?
C39 H39 0.9300 . ?
C40 C41 1.392(6) . ?
C40 H40 0.9300 . ?
C41 C42 1.316(6) . ?
C41 H41 0.9300 . ?
C42 C43 1.439(5) . ?
C42 H42 0.9300 . ?
C43 C44 1.387(5) . ?
C44 C45 1.360(5) . ?
C44 H44 0.9300 . ?
C45 C46 1.435(5) . ?
C45 H45 0.9300 . ?
C46 O4 1.317(4) . ?
C48 H00O 0.9300 . ?
N1 Ni1 1.907(3) . ?
N2 Ni1 1.855(3) . ?
N3 Ni2 1.856(3) . ?
N4 Ni2 1.803(3) . ?
O1 Ni1 1.863(2) . ?
O2 Ni1 1.922(2) . ?
O3 Ni2 1.807(2) . ?
O4 Ni2 1.862(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 C2 123.1(3) . . ?
O2 C1 C10 117.1(3) . . ?
C2 C1 C10 119.8(3) . . ?
C1 C2 C3 118.2(3) . . ?
C1 C2 C11 121.1(3) . . ?
C3 C2 C11 120.7(3) . . ?
C4 C3 C2 121.5(4) . . ?
C4 C3 C8 119.3(4) . . ?
C2 C3 C8 119.2(3) . . ?
C5 C4 C3 119.2(4) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 121.5(4) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C7 C6 C5 121.2(4) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 118.9(4) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
C9 C8 C7 119.1(4) . . ?
C9 C8 C3 121.1(3) . . ?
C7 C8 C3 119.9(4) . . ?
C10 C9 C8 119.5(4) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C1 122.1(3) . . ?
C9 C10 H10 119.0 . . ?
C1 C10 H10 119.0 . . ?
N2 C11 C2 126.7(3) . . ?
N2 C11 H11 116.7 . . ?
C2 C11 H11 116.7 . . ?
C13 C12 N2 108.4(3) . . ?
C13 C12 H12A 110.0 . . ?
N2 C12 H12A 110.0 . . ?
C13 C12 H12B 110.0 . . ?
N2 C12 H12B 110.0 . . ?
H12A C12 H12B 108.4 . . ?
C12 C13 N1 106.7(3) . . ?
C12 C13 H13A 110.4 . . ?
N1 C13 H13A 110.4 . . ?
C12 C13 H13B 110.4 . . ?
N1 C13 H13B 110.4 . . ?
H13A C13 H13B 108.6 . . ?
N1 C14 C15 123.9(3) . . ?
N1 C14 H14 118.0 . . ?
C15 C14 H14 118.0 . . ?
C14 C15 C23 120.7(3) . . ?
C14 C15 C16 118.7(3) . . ?
C23 C15 C16 120.4(3) . . ?
C47 C16 C17 118.9(4) . . ?
C47 C16 C15 117.2(3) . . ?
C17 C16 C15 124.0(3) . . ?
C18 C17 C16 121.6(4) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C19 118.7(4) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
C18 C19 C20 121.5(4) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C19 C20 C47 121.4(4) . . ?
C19 C20 H20 119.3 . . ?
C47 C20 H20 119.3 . . ?
C22 C21 C47 122.7(3) . . ?
C22 C21 H21 118.6 . . ?
C47 C21 H21 118.6 . . ?
C21 C22 C23 119.2(3) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
O1 C23 C22 114.3(3) . . ?
O1 C23 C15 125.6(3) . . ?
C22 C23 C15 120.1(3) . . ?
O3 C24 C48 115.9(3) . . ?
O3 C24 C25 127.0(3) . . ?
C48 C24 C25 117.0(3) . . ?
C33 C25 C24 117.8(3) . . ?
C33 C25 C26 119.6(3) . . ?
C24 C25 C26 122.6(3) . . ?
C31 C26 C27 115.7(4) . . ?
C31 C26 C25 118.3(3) . . ?
C27 C26 C25 126.0(3) . . ?
C28 C27 C26 123.9(4) . . ?
C28 C27 H27 118.1 . . ?
C26 C27 H27 118.1 . . ?
C29 C28 C27 120.2(4) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C28 C29 C30 117.3(4) . . ?
C28 C29 H29 121.4 . . ?
C30 C29 H29 121.4 . . ?
C29 C30 C31 124.1(4) . . ?
C29 C30 H30 118.0 . . ?
C31 C30 H30 118.0 . . ?
C26 C31 C32 117.0(4) . . ?
C26 C31 C30 118.9(4) . . ?
C32 C31 C30 124.1(4) . . ?
C48 C32 C31 124.3(3) . . ?
C48 C32 H32 117.9 . . ?
C31 C32 H32 117.9 . . ?
N3 C33 C25 125.1(3) . . ?
N3 C33 H33 117.4 . . ?
C25 C33 H33 117.4 . . ?
N3 C34 C35 108.1(3) . . ?
N3 C34 H34A 110.1 . . ?
C35 C34 H34A 110.1 . . ?
N3 C34 H34B 110.1 . . ?
C35 C34 H34B 110.1 . . ?
H34A C34 H34B 108.4 . . ?
N4 C35 C34 107.0(3) . . ?
N4 C35 H35A 110.3 . . ?
C34 C35 H35A 110.3 . . ?
N4 C35 H35B 110.3 . . ?
C34 C35 H35B 110.3 . . ?
H35A C35 H35B 108.6 . . ?
N4 C36 C37 127.2(3) . . ?
N4 C36 H36 116.4 . . ?
C37 C36 H36 116.4 . . ?
C46 C37 C36 118.6(3) . . ?
C46 C37 C38 119.1(3) . . ?
C36 C37 C38 121.9(3) . . ?
C39 C38 C43 115.9(4) . . ?
C39 C38 C37 122.8(3) . . ?
C43 C38 C37 121.3(3) . . ?
C38 C39 C40 120.4(4) . . ?
C38 C39 H39 119.8 . . ?
C40 C39 H39 119.8 . . ?
C41 C40 C39 123.2(4) . . ?
C41 C40 H40 118.4 . . ?
C39 C40 H40 118.4 . . ?
C42 C41 C40 118.1(4) . . ?
C42 C41 H41 121.0 . . ?
C40 C41 H41 121.0 . . ?
C41 C42 C43 119.8(4) . . ?
C41 C42 H42 120.1 . . ?
C43 C42 H42 120.1 . . ?
C44 C43 C38 117.3(4) . . ?
C44 C43 C42 120.2(4) . . ?
C38 C43 C42 122.5(4) . . ?
C45 C44 C43 121.3(4) . . ?
C45 C44 H44 119.3 . . ?
C43 C44 H44 119.3 . . ?
C44 C45 C46 123.9(3) . . ?
C44 C45 H45 118.1 . . ?
C46 C45 H45 118.1 . . ?
O4 C46 C37 123.6(3) . . ?
O4 C46 C45 119.3(3) . . ?
C37 C46 C45 117.0(3) . . ?
C20 C47 C16 117.8(4) . . ?
C20 C47 C21 121.9(4) . . ?
C16 C47 C21 120.3(3) . . ?
C32 C48 C24 120.7(4) . . ?
C32 C48 H00O 119.6 . . ?
C24 C48 H00O 119.6 . . ?
C14 N1 C13 117.3(3) . . ?
C14 N1 Ni1 127.9(2) . . ?
C13 N1 Ni1 114.5(2) . . ?
C11 N2 C12 119.7(3) . . ?
C11 N2 Ni1 125.6(2) . . ?
C12 N2 Ni1 114.7(2) . . ?
C33 N3 C34 117.5(3) . . ?
C33 N3 Ni2 129.8(2) . . ?
C34 N3 Ni2 112.7(2) . . ?
C36 N4 C35 119.8(3) . . ?
C36 N4 Ni2 128.0(2) . . ?
C35 N4 Ni2 111.9(2) . . ?
C23 O1 Ni1 126.0(2) . . ?
C1 O2 Ni1 128.1(2) . . ?
C24 O3 Ni2 128.7(2) . . ?
C46 O4 Ni2 130.3(2) . . ?
N2 Ni1 O1 178.64(10) . . ?
N2 Ni1 N1 84.99(12) . . ?
O1 Ni1 N1 94.95(11) . . ?
N2 Ni1 O2 95.27(12) . . ?
O1 Ni1 O2 84.85(10) . . ?
N1 Ni1 O2 177.13(10) . . ?
N4 Ni2 O3 176.77(10) . . ?
N4 Ni2 N3 88.91(12) . . ?
O3 Ni2 N3 91.29(12) . . ?
N4 Ni2 O4 91.20(12) . . ?
O3 Ni2 O4 88.68(10) . . ?
N3 Ni2 O4 178.62(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 C3 176.8(3) . . . . ?
C10 C1 C2 C3 -3.0(4) . . . . ?
O2 C1 C2 C11 -3.7(5) . . . . ?
C10 C1 C2 C11 176.5(3) . . . . ?
C1 C2 C3 C4 -178.5(3) . . . . ?
C11 C2 C3 C4 2.0(5) . . . . ?
C1 C2 C3 C8 0.0(5) . . . . ?
C11 C2 C3 C8 -179.5(3) . . . . ?
C2 C3 C4 C5 177.6(4) . . . . ?
C8 C3 C4 C5 -0.9(6) . . . . ?
C3 C4 C5 C6 0.8(7) . . . . ?
C4 C5 C6 C7 0.1(7) . . . . ?
C5 C6 C7 C8 -0.8(7) . . . . ?
C6 C7 C8 C9 178.8(4) . . . . ?
C6 C7 C8 C3 0.7(6) . . . . ?
C4 C3 C8 C9 -177.9(3) . . . . ?
C2 C3 C8 C9 3.5(5) . . . . ?
C4 C3 C8 C7 0.2(5) . . . . ?
C2 C3 C8 C7 -178.4(3) . . . . ?
C7 C8 C9 C10 178.0(4) . . . . ?
C3 C8 C9 C10 -3.9(5) . . . . ?
C8 C9 C10 C1 0.7(5) . . . . ?
O2 C1 C10 C9 -177.0(3) . . . . ?
C2 C1 C10 C9 2.8(5) . . . . ?
C1 C2 C11 N2 0.9(5) . . . . ?
C3 C2 C11 N2 -179.6(3) . . . . ?
N2 C12 C13 N1 33.7(3) . . . . ?
N1 C14 C15 C23 -7.3(5) . . . . ?
N1 C14 C15 C16 178.7(3) . . . . ?
C14 C15 C16 C47 170.8(3) . . . . ?
C23 C15 C16 C47 -3.3(4) . . . . ?
C14 C15 C16 C17 -8.8(5) . . . . ?
C23 C15 C16 C17 177.1(3) . . . . ?
C47 C16 C17 C18 -2.0(5) . . . . ?
C15 C16 C17 C18 177.6(3) . . . . ?
C16 C17 C18 C19 0.4(6) . . . . ?
C17 C18 C19 C20 1.3(6) . . . . ?
C18 C19 C20 C47 -1.4(6) . . . . ?
C47 C21 C22 C23 -0.7(5) . . . . ?
C21 C22 C23 O1 -179.5(3) . . . . ?
C21 C22 C23 C15 -1.0(5) . . . . ?
C14 C15 C23 O1 7.4(5) . . . . ?
C16 C15 C23 O1 -178.6(3) . . . . ?
C14 C15 C23 C22 -170.9(3) . . . . ?
C16 C15 C23 C22 3.0(4) . . . . ?
O3 C24 C25 C33 4.7(5) . . . . ?
C48 C24 C25 C33 -176.3(3) . . . . ?
O3 C24 C25 C26 -176.3(3) . . . . ?
C48 C24 C25 C26 2.7(5) . . . . ?
C33 C25 C26 C31 178.8(3) . . . . ?
C24 C25 C26 C31 -0.2(5) . . . . ?
C33 C25 C26 C27 -2.5(5) . . . . ?
C24 C25 C26 C27 178.5(3) . . . . ?
C31 C26 C27 C28 0.7(6) . . . . ?
C25 C26 C27 C28 -178.0(4) . . . . ?
C26 C27 C28 C29 0.3(7) . . . . ?
C27 C28 C29 C30 -1.0(7) . . . . ?
C28 C29 C30 C31 0.7(7) . . . . ?
C27 C26 C31 C32 178.8(3) . . . . ?
C25 C26 C31 C32 -2.4(5) . . . . ?
C27 C26 C31 C30 -1.0(5) . . . . ?
C25 C26 C31 C30 177.8(3) . . . . ?
C29 C30 C31 C26 0.4(6) . . . . ?
C29 C30 C31 C32 -179.4(4) . . . . ?
C26 C31 C32 C48 2.7(5) . . . . ?
C30 C31 C32 C48 -177.5(4) . . . . ?
C24 C25 C33 N3 -1.2(5) . . . . ?
C26 C25 C33 N3 179.7(3) . . . . ?
N3 C34 C35 N4 -35.3(3) . . . . ?
N4 C36 C37 C46 8.3(5) . . . . ?
N4 C36 C37 C38 -178.2(3) . . . . ?
C46 C37 C38 C39 -176.4(3) . . . . ?
C36 C37 C38 C39 10.1(5) . . . . ?
C46 C37 C38 C43 3.6(5) . . . . ?
C36 C37 C38 C43 -169.9(3) . . . . ?
C43 C38 C39 C40 2.7(5) . . . . ?
C37 C38 C39 C40 -177.3(3) . . . . ?
C38 C39 C40 C41 -1.3(7) . . . . ?
C39 C40 C41 C42 -0.5(7) . . . . ?
C40 C41 C42 C43 0.6(6) . . . . ?
C39 C38 C43 C44 178.8(3) . . . . ?
C37 C38 C43 C44 -1.2(5) . . . . ?
C39 C38 C43 C42 -2.6(5) . . . . ?
C37 C38 C43 C42 177.4(3) . . . . ?
C41 C42 C43 C44 179.5(4) . . . . ?
C41 C42 C43 C38 1.0(6) . . . . ?
C38 C43 C44 C45 -0.7(5) . . . . ?
C42 C43 C44 C45 -179.3(3) . . . . ?
C43 C44 C45 C46 0.2(6) . . . . ?
C36 C37 C46 O4 -7.6(5) . . . . ?
C38 C37 C46 O4 178.7(3) . . . . ?
C36 C37 C46 C45 169.9(3) . . . . ?
C38 C37 C46 C45 -3.8(4) . . . . ?
C44 C45 C46 O4 179.7(3) . . . . ?
C44 C45 C46 C37 2.1(5) . . . . ?
C19 C20 C47 C16 -0.3(6) . . . . ?
C19 C20 C47 C21 -179.7(3) . . . . ?
C17 C16 C47 C20 1.9(5) . . . . ?
C15 C16 C47 C20 -177.7(3) . . . . ?
C17 C16 C47 C21 -178.7(3) . . . . ?
C15 C16 C47 C21 1.7(5) . . . . ?
C22 C21 C47 C20 179.7(3) . . . . ?
C22 C21 C47 C16 0.3(5) . . . . ?
C31 C32 C48 C24 -0.1(6) . . . . ?
O3 C24 C48 C32 176.5(3) . . . . ?
C25 C24 C48 C32 -2.6(5) . . . . ?
C15 C14 N1 C13 171.8(3) . . . . ?
C15 C14 N1 Ni1 -1.7(5) . . . . ?
C12 C13 N1 C14 153.4(3) . . . . ?
C12 C13 N1 Ni1 -32.2(3) . . . . ?
C2 C11 N2 C12 179.0(3) . . . . ?
C2 C11 N2 Ni1 0.2(5) . . . . ?
C13 C12 N2 C11 157.1(3) . . . . ?
C13 C12 N2 Ni1 -23.9(3) . . . . ?
C25 C33 N3 C34 -178.9(3) . . . . ?
C25 C33 N3 Ni2 -0.4(5) . . . . ?
C35 C34 N3 C33 -157.3(3) . . . . ?
C35 C34 N3 Ni2 24.0(3) . . . . ?
C37 C36 N4 C35 -171.1(3) . . . . ?
C37 C36 N4 Ni2 1.3(5) . . . . ?
C34 C35 N4 C36 -154.1(3) . . . . ?
C34 C35 N4 Ni2 32.3(3) . . . . ?
C22 C23 O1 Ni1 -179.89(19) . . . . ?
C15 C23 O1 Ni1 1.7(4) . . . . ?
C2 C1 O2 Ni1 5.4(4) . . . . ?
C10 C1 O2 Ni1 -174.82(19) . . . . ?
C48 C24 O3 Ni2 174.5(2) . . . . ?
C25 C24 O3 Ni2 -6.5(5) . . . . ?
C37 C46 O4 Ni2 -2.1(4) . . . . ?
C45 C46 O4 Ni2 -179.5(2) . . . . ?
C11 N2 Ni1 N1 -176.3(3) . . . . ?
C12 N2 Ni1 N1 4.8(2) . . . . ?
C11 N2 Ni1 O2 0.8(3) . . . . ?
C12 N2 Ni1 O2 -178.1(2) . . . . ?
C23 O1 Ni1 N1 -7.8(2) . . . . ?
C23 O1 Ni1 O2 175.1(2) . . . . ?
C36 N4 Ni2 N3 170.7(3) . . . . ?
C35 N4 Ni2 N3 -16.3(2) . . . . ?
C36 N4 Ni2 O4 -7.9(3) . . . . ?
C35 N4 Ni2 O4 165.0(2) . . . . ?
C24 O3 Ni2 N3 3.7(3) . . . . ?
C24 O3 Ni2 O4 -177.7(3) . . . . ?
C33 N3 Ni2 N4 176.3(3) . . . . ?
C34 N3 Ni2 N4 -5.2(2) . . . . ?
C33 N3 Ni2 O3 -0.5(3) . . . . ?
C34 N3 Ni2 O3 178.0(2) . . . . ?
C46 O4 Ni2 N4 8.6(3) . . . . ?
C46 O4 Ni2 O3 -174.6(3) . . . . ?

_refine_diff_density_max         0.934
_refine_diff_density_min         -0.727
_refine_diff_density_rms         0.104

