# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_f
_database_code_depnum_ccdc_archive 'CCDC 2179951'
loop_
_audit_author_name
_audit_author_address
'Paula Brandao'
;Universidade de Aveiro
Portugal
;
_audit_update_record             
;
2022-06-17 deposited with the CCDC.	2023-02-21 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            'C22 H36 Cu N4 O5'
_chemical_formula_weight         500.09

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

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

_cell_length_a                   16.0184(6)
_cell_length_b                   17.2661(7)
_cell_length_c                   8.8793(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2455.79(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    491
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      25.10

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_F_000             1060
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.928
_shelx_estimated_absorpt_T_min   0.851
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6915
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            68421
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.359
_diffrn_reflns_theta_max         27.154
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2719
_reflns_number_gt                2127
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_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)+(0.0445P)²+4.2409P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2719
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.1176
_refine_ls_wR_factor_gt          0.1047
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_restrained_S_all      1.131
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.500000 0.500000 0.500000 0.02030(15) Uani 1 2 d S . P . .
O1 O 0.52890(11) 0.40022(10) 0.61268(19) 0.0227(4) Uani 1 1 d . . . . .
N1 N 0.38055(13) 0.45703(13) 0.4805(2) 0.0209(4) Uani 1 1 d . . . . .
N2 N 0.51918(14) 0.43508(14) 0.2918(2) 0.0256(5) Uani 1 1 d . . . . .
H2A H 0.510(2) 0.391(2) 0.324(4) 0.032(9) Uiso 1 1 d . . . . .
C1 C 0.47828(16) 0.36478(14) 0.7057(3) 0.0209(5) Uani 1 1 d . . . . .
C2 C 0.51104(17) 0.31908(15) 0.8246(3) 0.0267(5) Uani 1 1 d . . . . .
H2 H 0.569850 0.315569 0.836661 0.032 Uiso 1 1 calc R U . . .
C3 C 0.46003(19) 0.27969(16) 0.9231(3) 0.0317(6) Uani 1 1 d . . . . .
H3 H 0.484178 0.250238 1.002315 0.038 Uiso 1 1 calc R U . . .
C4 C 0.37307(19) 0.28242(16) 0.9083(3) 0.0322(6) Uani 1 1 d . . . . .
H4 H 0.338021 0.255715 0.977223 0.039 Uiso 1 1 calc R U . . .
C5 C 0.33948(17) 0.32464(15) 0.7916(3) 0.0272(6) Uani 1 1 d . . . . .
H5 H 0.280602 0.325175 0.778770 0.033 Uiso 1 1 calc R U . . .
C6 C 0.38938(15) 0.36697(14) 0.6908(3) 0.0214(5) Uani 1 1 d . . . . .
C7 C 0.34835(15) 0.40558(15) 0.5660(3) 0.0223(5) Uani 1 1 d . . . . .
H7 H 0.292176 0.391251 0.546027 0.027 Uiso 1 1 calc R U . . .
C8 C 0.33294(17) 0.47948(17) 0.3456(3) 0.0287(6) Uani 1 1 d . . . . .
H8A H 0.336800 0.536147 0.330089 0.034 Uiso 1 1 calc R U . . .
H8B H 0.273389 0.465651 0.358581 0.034 Uiso 1 1 calc R U . . .
C9 C 0.36919(18) 0.43687(18) 0.2096(3) 0.0340(7) Uani 1 1 d . . . . .
H9A H 0.363818 0.380512 0.227626 0.041 Uiso 1 1 calc R U . . .
H9B H 0.334575 0.449546 0.120539 0.041 Uiso 1 1 calc R U . . .
C10 C 0.45935(18) 0.45404(17) 0.1713(3) 0.0302(6) Uani 1 1 d . . . . .
H10A H 0.474665 0.424445 0.079866 0.036 Uiso 1 1 calc R U . . .
H10B H 0.464539 0.509788 0.146960 0.036 Uiso 1 1 calc R U . . .
C11 C 0.60511(18) 0.42988(18) 0.2320(3) 0.0338(6) Uani 1 1 d . . . . .
H11A H 0.607108 0.390903 0.151812 0.051 Uiso 1 1 calc R U . . .
H11B H 0.643337 0.414993 0.313112 0.051 Uiso 1 1 calc R U . . .
H11C H 0.621840 0.480305 0.191250 0.051 Uiso 1 1 calc R U . . .
O100 O 0.750000 0.250000 0.2887(3) 0.0347(7) Uani 1 2 d S T P . .
H10C H 0.772(2) 0.229(2) 0.342(4) 0.035(10) Uiso 1 1 d . . . . .
O200 O 0.6670(2) 0.3141(2) 0.5319(3) 0.0591(9) Uani 1 1 d . . . . .
H20A H 0.635(3) 0.337(3) 0.554(5) 0.059(15) Uiso 1 1 d . . . . .
H20B H 0.686(3) 0.300(3) 0.597(5) 0.060(14) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 2.0454(17) 5_666 ?
Cu1 O1 2.0454(17) . ?
Cu1 N1 2.059(2) 5_666 ?
Cu1 N1 2.059(2) . ?
Cu1 N2 2.183(2) . ?
Cu1 N2 2.183(2) 5_666 ?
O1 C1 1.309(3) . ?
N1 C7 1.278(3) . ?
N1 C8 1.471(3) . ?
N2 C10 1.474(4) . ?
N2 C11 1.478(3) . ?
N2 H2A 0.82(3) . ?
C1 C2 1.419(3) . ?
C1 C6 1.431(3) . ?
C2 C3 1.377(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.400(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.405(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.450(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.529(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.513(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
O100 H10C 0.70(3) . ?
O100 H10C 0.70(3) 2_655 ?
O200 H20A 0.67(5) . ?
O200 H20B 0.69(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 180.0 5_666 . ?
O1 Cu1 N1 87.03(8) 5_666 5_666 ?
O1 Cu1 N1 92.97(8) . 5_666 ?
O1 Cu1 N1 92.97(8) 5_666 . ?
O1 Cu1 N1 87.02(8) . . ?
N1 Cu1 N1 180.0 5_666 . ?
O1 Cu1 N2 92.87(8) 5_666 . ?
O1 Cu1 N2 87.13(8) . . ?
N1 Cu1 N2 97.21(8) 5_666 . ?
N1 Cu1 N2 82.79(8) . . ?
O1 Cu1 N2 87.13(8) 5_666 5_666 ?
O1 Cu1 N2 92.87(8) . 5_666 ?
N1 Cu1 N2 82.79(8) 5_666 5_666 ?
N1 Cu1 N2 97.21(8) . 5_666 ?
N2 Cu1 N2 180.0 . 5_666 ?
C1 O1 Cu1 124.20(15) . . ?
C7 N1 C8 117.2(2) . . ?
C7 N1 Cu1 125.13(17) . . ?
C8 N1 Cu1 117.08(16) . . ?
C10 N2 C11 111.0(2) . . ?
C10 N2 Cu1 114.17(17) . . ?
C11 N2 Cu1 117.82(17) . . ?
C10 N2 H2A 110(2) . . ?
C11 N2 H2A 104(2) . . ?
Cu1 N2 H2A 99(2) . . ?
O1 C1 C2 120.0(2) . . ?
O1 C1 C6 123.1(2) . . ?
C2 C1 C6 116.8(2) . . ?
C3 C2 C1 121.9(3) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C2 C3 C4 120.9(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 118.5(3) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 C6 122.2(3) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C5 C6 C1 119.6(2) . . ?
C5 C6 C7 117.9(2) . . ?
C1 C6 C7 122.3(2) . . ?
N1 C7 C6 126.2(2) . . ?
N1 C7 H7 116.9 . . ?
C6 C7 H7 116.9 . . ?
N1 C8 C9 108.6(2) . . ?
N1 C8 H8A 110.0 . . ?
C9 C8 H8A 110.0 . . ?
N1 C8 H8B 110.0 . . ?
C9 C8 H8B 110.0 . . ?
H8A C8 H8B 108.3 . . ?
C10 C9 C8 116.5(2) . . ?
C10 C9 H9A 108.2 . . ?
C8 C9 H9A 108.2 . . ?
C10 C9 H9B 108.2 . . ?
C8 C9 H9B 108.2 . . ?
H9A C9 H9B 107.3 . . ?
N2 C10 C9 114.5(2) . . ?
N2 C10 H10A 108.6 . . ?
C9 C10 H10A 108.6 . . ?
N2 C10 H10B 108.6 . . ?
C9 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
H10C O100 H10C 94(5) . 2_655 ?
H20A O200 H20B 106(5) . . ?

_refine_diff_density_max         0.447
_refine_diff_density_min         -0.696
_refine_diff_density_rms         0.073



####################################################################### 
# 
# 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_f_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2179957'
loop_
_audit_author_name
_audit_author_address
'Paula Brandao'
;Universidade de Aveiro
Portugal
;
_audit_update_record             
;
2022-06-17 deposited with the CCDC.	2023-02-21 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            'C50 H70 Cl2 N12 Ni2 O12'
_chemical_formula_weight         1219.50

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.5595(5)
_cell_length_b                   12.9431(7)
_cell_length_c                   20.8682(11)
_cell_angle_alpha                90
_cell_angle_beta                 98.743(2)
_cell_angle_gamma                90
_cell_volume                     2819.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    512
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      25.08

_exptl_crystal_description       Block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_F_000             1280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.833
_shelx_estimated_absorpt_T_min   0.813
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6454
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            77937
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.858
_diffrn_reflns_theta_max         27.129
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6226
_reflns_number_gt                5407
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_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)+(0.0352P)²+3.1742P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6226
_refine_ls_number_parameters     373
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0916
_refine_ls_wR_factor_gt          0.0857
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 1.000000 1.000000 0.500000 0.01494(8) Uani 1 2 d S . P . .
O1 O 0.90737(12) 0.87844(10) 0.44925(6) 0.0205(3) Uani 1 1 d . . . . .
N1 N 1.16684(14) 0.93285(11) 0.48252(7) 0.0189(3) Uani 1 1 d . . . . .
N2 N 1.02458(15) 0.89695(12) 0.58368(7) 0.0202(3) Uani 1 1 d . . . . .
H2A H 1.021(2) 0.8407(19) 0.5623(11) 0.026(6) Uiso 1 1 d . . . . .
C1 C 0.94450(18) 0.83595(13) 0.39779(8) 0.0199(3) Uani 1 1 d . . . . .
C2 C 0.8546(2) 0.78109(16) 0.35286(9) 0.0272(4) Uani 1 1 d . . . . .
H2 H 0.767652 0.777808 0.359536 0.033 Uiso 1 1 calc R U . . .
C3 C 0.8910(2) 0.73226(18) 0.29950(10) 0.0354(5) Uani 1 1 d . . . . .
H3 H 0.829711 0.693648 0.271119 0.043 Uiso 1 1 calc R U . . .
C4 C 1.0166(2) 0.7392(2) 0.28705(10) 0.0387(5) Uani 1 1 d . . . . .
H4 H 1.040368 0.707855 0.249477 0.046 Uiso 1 1 calc R U . . .
C5 C 1.1060(2) 0.79207(17) 0.32976(10) 0.0315(5) Uani 1 1 d . . . . .
H5 H 1.191558 0.796999 0.321148 0.038 Uiso 1 1 calc R U . . .
C6 C 1.07337(19) 0.83885(14) 0.38580(9) 0.0220(4) Uani 1 1 d . . . . .
C7 C 1.17827(18) 0.87599(14) 0.43363(9) 0.0216(4) Uani 1 1 d . . . . .
H7 H 1.262558 0.856266 0.428036 0.026 Uiso 1 1 calc R U . . .
C8 C 1.27970(17) 0.94212(14) 0.53302(9) 0.0218(4) Uani 1 1 d . . . . .
H8A H 1.290029 1.014732 0.547801 0.026 Uiso 1 1 calc R U . . .
H8B H 1.357726 0.921525 0.515264 0.026 Uiso 1 1 calc R U . . .
C9 C 1.26200(19) 0.87231(15) 0.59004(9) 0.0244(4) Uani 1 1 d . . . . .
H9A H 1.248654 0.800621 0.573874 0.029 Uiso 1 1 calc R U . . .
H9B H 1.342157 0.873228 0.621559 0.029 Uiso 1 1 calc R U . . .
C10 C 1.15122(19) 0.90137(15) 0.62545(9) 0.0243(4) Uani 1 1 d . . . . .
H10A H 1.150612 0.853947 0.662619 0.029 Uiso 1 1 calc R U . . .
H10B H 1.165318 0.972252 0.642916 0.029 Uiso 1 1 calc R U . . .
C11 C 0.9205(2) 0.89282(16) 0.62352(9) 0.0273(4) Uani 1 1 d . . . . .
H11A H 0.928067 0.829141 0.649227 0.041 Uiso 1 1 calc R U . . .
H11B H 0.837549 0.893911 0.595173 0.041 Uiso 1 1 calc R U . . .
H11C H 0.926900 0.952654 0.652608 0.041 Uiso 1 1 calc R U . . .
Ni2 Ni 0.500000 0.500000 0.500000 0.01707(9) Uani 1 2 d S . P . .
O2 O 0.40861(12) 0.54452(10) 0.57673(6) 0.0217(3) Uani 1 1 d . . . . .
N3 N 0.34628(15) 0.56720(12) 0.43804(7) 0.0207(3) Uani 1 1 d . . . . .
N4 N 0.43621(17) 0.38681(14) 0.31683(9) 0.0274(4) Uani 1 1 d . . . . .
H4A H 0.455(3) 0.426(2) 0.2824(13) 0.037(7) Uiso 1 1 d . . . . .
H4B H 0.494(3) 0.411(2) 0.3547(13) 0.039(7) Uiso 1 1 d . . . . .
N5 N 0.58648(15) 0.64412(12) 0.50275(8) 0.0210(3) Uani 1 1 d . . . . .
N6 N 0.71175(16) 0.77611(13) 0.48961(9) 0.0251(3) Uani 1 1 d . . . . .
H6 H 0.773(3) 0.811(2) 0.4788(12) 0.036(7) Uiso 1 1 d . . . . .
C12 C 0.28628(17) 0.56545(13) 0.57604(9) 0.0204(4) Uani 1 1 d . . . . .
C13 C 0.2341(2) 0.56447(16) 0.63461(10) 0.0285(4) Uani 1 1 d . . . . .
H13 H 0.287529 0.545684 0.673677 0.034 Uiso 1 1 calc R U . . .
C14 C 0.1083(2) 0.58988(18) 0.63671(11) 0.0348(5) Uani 1 1 d . . . . .
H14 H 0.076896 0.588850 0.677026 0.042 Uiso 1 1 calc R U . . .
C15 C 0.0260(2) 0.61718(17) 0.58034(11) 0.0322(5) Uani 1 1 d . . . . .
H15 H -0.060798 0.634805 0.581965 0.039 Uiso 1 1 calc R U . . .
C16 C 0.07325(19) 0.61802(15) 0.52247(10) 0.0270(4) Uani 1 1 d . . . . .
H16 H 0.017954 0.637040 0.484033 0.032 Uiso 1 1 calc R U . . .
C17 C 0.20159(18) 0.59145(14) 0.51846(9) 0.0218(4) Uani 1 1 d . . . . .
C18 C 0.24072(18) 0.59821(14) 0.45480(9) 0.0226(4) Uani 1 1 d . . . . .
H18 H 0.181110 0.629238 0.421695 0.027 Uiso 1 1 calc R U . . .
C19 C 0.3620(2) 0.59292(16) 0.37023(10) 0.0294(4) Uani 1 1 d . . . . .
H19A H 0.452735 0.582581 0.364886 0.035 Uiso 1 1 calc R U . . .
H19B H 0.340997 0.666732 0.361976 0.035 Uiso 1 1 calc R U . . .
C20 C 0.2769(2) 0.5270(2) 0.32031(11) 0.0372(5) Uani 1 1 d . . . . .
H20A H 0.186263 0.539929 0.324853 0.045 Uiso 1 1 calc R U . . .
H20B H 0.289036 0.549977 0.276405 0.045 Uiso 1 1 calc R U . . .
C21 C 0.3016(2) 0.41166(19) 0.32560(11) 0.0342(5) Uani 1 1 d . . . . .
H21A H 0.286220 0.387041 0.368665 0.041 Uiso 1 1 calc R U . . .
H21B H 0.241344 0.375203 0.292162 0.041 Uiso 1 1 calc R U . . .
C22 C 0.4577(2) 0.27488(17) 0.30599(11) 0.0371(5) Uani 1 1 d . . . . .
H22A H 0.432003 0.234794 0.341730 0.056 Uiso 1 1 calc R U . . .
H22B H 0.548659 0.262866 0.304077 0.056 Uiso 1 1 calc R U . . .
H22C H 0.406497 0.253294 0.265024 0.056 Uiso 1 1 calc R U . . .
C23 C 0.69351(18) 0.67379(14) 0.48258(9) 0.0234(4) Uani 1 1 d . . . . .
H23 H 0.750436 0.628418 0.465282 0.028 Uiso 1 1 calc R U . . .
C24 C 0.6102(2) 0.81482(15) 0.51539(11) 0.0294(4) Uani 1 1 d . . . . .
H24 H 0.595994 0.884924 0.525777 0.035 Uiso 1 1 calc R U . . .
C25 C 0.53348(19) 0.73291(14) 0.52318(10) 0.0263(4) Uani 1 1 d . . . . .
H25 H 0.455087 0.736479 0.540175 0.032 Uiso 1 1 calc R U . . .
Cl1 Cl 0.58037(6) 0.47511(5) 0.17776(3) 0.04038(14) Uani 1 1 d . . . . .
O102 O 0.4856(2) 0.52103(17) 0.21240(10) 0.0640(6) Uani 1 1 d . . . . .
O103 O 0.5492(2) 0.49241(19) 0.11064(9) 0.0638(6) Uani 1 1 d . . . . .
O101 O 0.5914(2) 0.36894(17) 0.19361(13) 0.0733(7) Uani 1 1 d . . . . .
O104 O 0.7022(2) 0.5235(2) 0.19999(13) 0.0814(8) 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
Ni1 N1 2.0464(15) . ?
Ni1 N1 2.0464(15) 3_776 ?
Ni1 O1 2.0588(12) . ?
Ni1 O1 2.0589(12) 3_776 ?
Ni1 N2 2.1813(15) . ?
Ni1 N2 2.1814(15) 3_776 ?
O1 C1 1.318(2) . ?
N1 C7 1.278(2) . ?
N1 C8 1.471(2) . ?
N2 C11 1.476(2) . ?
N2 C10 1.482(2) . ?
N2 H2A 0.85(2) . ?
C1 C2 1.419(3) . ?
C1 C6 1.421(3) . ?
C2 C3 1.385(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.393(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.378(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.405(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.455(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.528(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.523(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
Ni2 O2 2.0728(13) 3_666 ?
Ni2 O2 2.0729(13) . ?
Ni2 N5 2.0738(15) 3_666 ?
Ni2 N5 2.0738(15) . ?
Ni2 N3 2.1035(16) 3_666 ?
Ni2 N3 2.1035(16) . ?
O2 C12 1.318(2) . ?
N3 C18 1.282(2) . ?
N3 C19 1.488(2) . ?
N4 C22 1.489(3) . ?
N4 C21 1.495(3) . ?
N4 H4A 0.93(3) . ?
N4 H4B 0.97(3) . ?
N5 C23 1.322(2) . ?
N5 C25 1.374(2) . ?
N6 C23 1.343(2) . ?
N6 C24 1.366(3) . ?
N6 H6 0.84(3) . ?
C12 C13 1.415(3) . ?
C12 C17 1.425(3) . ?
C13 C14 1.376(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.397(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.375(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.413(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.453(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.528(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.517(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23 0.9500 . ?
C24 C25 1.359(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
Cl1 O103 1.407(2) . ?
Cl1 O101 1.414(2) . ?
Cl1 O104 1.442(3) . ?
Cl1 O102 1.4479(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ni1 N1 180.0 . 3_776 ?
N1 Ni1 O1 86.46(6) . . ?
N1 Ni1 O1 93.54(6) 3_776 . ?
N1 Ni1 O1 93.54(6) . 3_776 ?
N1 Ni1 O1 86.46(6) 3_776 3_776 ?
O1 Ni1 O1 180.00(8) . 3_776 ?
N1 Ni1 N2 83.23(6) . . ?
N1 Ni1 N2 96.77(6) 3_776 . ?
O1 Ni1 N2 86.21(6) . . ?
O1 Ni1 N2 93.79(6) 3_776 . ?
N1 Ni1 N2 96.77(6) . 3_776 ?
N1 Ni1 N2 83.23(6) 3_776 3_776 ?
O1 Ni1 N2 93.79(6) . 3_776 ?
O1 Ni1 N2 86.21(6) 3_776 3_776 ?
N2 Ni1 N2 180.0 . 3_776 ?
C1 O1 Ni1 124.13(11) . . ?
C7 N1 C8 117.02(15) . . ?
C7 N1 Ni1 125.10(13) . . ?
C8 N1 Ni1 117.60(11) . . ?
C11 N2 C10 110.64(15) . . ?
C11 N2 Ni1 117.70(12) . . ?
C10 N2 Ni1 115.73(11) . . ?
C11 N2 H2A 106.6(16) . . ?
C10 N2 H2A 107.9(16) . . ?
Ni1 N2 H2A 96.5(16) . . ?
O1 C1 C2 119.67(17) . . ?
O1 C1 C6 122.94(16) . . ?
C2 C1 C6 117.35(17) . . ?
C3 C2 C1 121.3(2) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 120.6(2) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 119.33(19) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 121.5(2) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 119.83(18) . . ?
C5 C6 C7 117.12(18) . . ?
C1 C6 C7 122.50(16) . . ?
N1 C7 C6 125.67(17) . . ?
N1 C7 H7 117.2 . . ?
C6 C7 H7 117.2 . . ?
N1 C8 C9 109.15(15) . . ?
N1 C8 H8A 109.9 . . ?
C9 C8 H8A 109.9 . . ?
N1 C8 H8B 109.9 . . ?
C9 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
C10 C9 C8 115.20(16) . . ?
C10 C9 H9A 108.5 . . ?
C8 C9 H9A 108.5 . . ?
C10 C9 H9B 108.5 . . ?
C8 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
N2 C10 C9 113.33(15) . . ?
N2 C10 H10A 108.9 . . ?
C9 C10 H10A 108.9 . . ?
N2 C10 H10B 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 Ni2 O2 180.0 3_666 . ?
O2 Ni2 N5 89.05(6) 3_666 3_666 ?
O2 Ni2 N5 90.95(6) . 3_666 ?
O2 Ni2 N5 90.95(6) 3_666 . ?
O2 Ni2 N5 89.05(6) . . ?
N5 Ni2 N5 180.0 3_666 . ?
O2 Ni2 N3 87.34(6) 3_666 3_666 ?
O2 Ni2 N3 92.66(6) . 3_666 ?
N5 Ni2 N3 86.59(6) 3_666 3_666 ?
N5 Ni2 N3 93.41(6) . 3_666 ?
O2 Ni2 N3 92.66(6) 3_666 . ?
O2 Ni2 N3 87.34(6) . . ?
N5 Ni2 N3 93.41(6) 3_666 . ?
N5 Ni2 N3 86.59(6) . . ?
N3 Ni2 N3 180.0 3_666 . ?
C12 O2 Ni2 128.27(12) . . ?
C18 N3 C19 114.64(16) . . ?
C18 N3 Ni2 125.69(13) . . ?
C19 N3 Ni2 119.33(12) . . ?
C22 N4 C21 113.42(18) . . ?
C22 N4 H4A 111.4(16) . . ?
C21 N4 H4A 107.0(16) . . ?
C22 N4 H4B 110.4(16) . . ?
C21 N4 H4B 108.6(16) . . ?
H4A N4 H4B 106(2) . . ?
C23 N5 C25 105.31(15) . . ?
C23 N5 Ni2 130.31(13) . . ?
C25 N5 Ni2 124.22(12) . . ?
C23 N6 C24 107.24(16) . . ?
C23 N6 H6 127.0(18) . . ?
C24 N6 H6 125.7(18) . . ?
O2 C12 C13 119.90(17) . . ?
O2 C12 C17 123.12(16) . . ?
C13 C12 C17 116.97(17) . . ?
C14 C13 C12 122.0(2) . . ?
C14 C13 H13 119.0 . . ?
C12 C13 H13 119.0 . . ?
C13 C14 C15 120.9(2) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C16 C15 C14 118.63(19) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
C15 C16 C17 121.97(19) . . ?
C15 C16 H16 119.0 . . ?
C17 C16 H16 119.0 . . ?
C16 C17 C12 119.49(17) . . ?
C16 C17 C18 116.63(17) . . ?
C12 C17 C18 123.79(17) . . ?
N3 C18 C17 127.62(17) . . ?
N3 C18 H18 116.2 . . ?
C17 C18 H18 116.2 . . ?
N3 C19 C20 112.59(18) . . ?
N3 C19 H19A 109.1 . . ?
C20 C19 H19A 109.1 . . ?
N3 C19 H19B 109.1 . . ?
C20 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
C21 C20 C19 115.00(18) . . ?
C21 C20 H20A 108.5 . . ?
C19 C20 H20A 108.5 . . ?
C21 C20 H20B 108.5 . . ?
C19 C20 H20B 108.5 . . ?
H20A C20 H20B 107.5 . . ?
N4 C21 C20 111.06(18) . . ?
N4 C21 H21A 109.4 . . ?
C20 C21 H21A 109.4 . . ?
N4 C21 H21B 109.4 . . ?
C20 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
N4 C22 H22A 109.5 . . ?
N4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N5 C23 N6 111.54(17) . . ?
N5 C23 H23 124.2 . . ?
N6 C23 H23 124.2 . . ?
C25 C24 N6 106.19(17) . . ?
C25 C24 H24 126.9 . . ?
N6 C24 H24 126.9 . . ?
C24 C25 N5 109.71(17) . . ?
C24 C25 H25 125.1 . . ?
N5 C25 H25 125.1 . . ?
O103 Cl1 O101 112.69(16) . . ?
O103 Cl1 O104 108.28(15) . . ?
O101 Cl1 O104 107.99(17) . . ?
O103 Cl1 O102 110.88(13) . . ?
O101 Cl1 O102 108.70(13) . . ?
O104 Cl1 O102 108.16(17) . . ?

_refine_diff_density_max         0.917
_refine_diff_density_min         -0.972
_refine_diff_density_rms         0.058



