# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_Co1
_database_code_depnum_ccdc_archive 'CCDC 2308477'
loop_
_audit_author_name
_audit_author_address
'M. Fatima C. Guedes da Silva'
;University of Lisbon, Portugal
Portugal
;
_audit_update_record             
;
2023-11-16 deposited with the CCDC.	2024-04-25 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 H20 Co N6 O8'
_chemical_formula_weight         579.39

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 '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                   7.6976(5)
_cell_length_b                   7.8986(5)
_cell_length_c                   10.9820(7)
_cell_angle_alpha                108.974(3)
_cell_angle_beta                 90.541(3)
_cell_angle_gamma                114.662(3)
_cell_volume                     565.59(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9851
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      26.12

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_F_000             297
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.827
_shelx_estimated_absorpt_T_min   0.755
_shelx_estimated_absorpt_T_max   0.900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.704
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26886
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.954
_diffrn_reflns_theta_max         26.145
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2250
_reflns_number_gt                2141
_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_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR-97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_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)+(0.0234P)²+0.2650P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2250
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0238
_refine_ls_R_factor_gt           0.0218
_refine_ls_wR_factor_ref         0.0588
_refine_ls_wR_factor_gt          0.0574
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.118
_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
C1 C 0.0993(2) -0.2688(2) 0.29328(14) 0.0266(3) Uani 1 1 d . . . . .
C2 C -0.0225(2) -0.2570(2) 0.40028(13) 0.0241(3) Uani 1 1 d . . . . .
C3 C 0.0308(2) -0.2705(2) 0.51694(14) 0.0288(3) Uani 1 1 d . . . . .
H3 H 0.145660 -0.278920 0.531378 0.035 Uiso 1 1 calc R U . . .
C4 C -0.0869(2) -0.2714(2) 0.61157(14) 0.0295(3) Uani 1 1 d . . . . .
H4 H -0.053755 -0.286385 0.687762 0.035 Uiso 1 1 calc R U . . .
C5 C -0.2548(2) -0.2499(2) 0.59299(13) 0.0247(3) Uani 1 1 d . . . . .
C6 C -0.3070(2) -0.2325(2) 0.47768(14) 0.0278(3) Uani 1 1 d . . . . .
H6 H -0.418081 -0.216429 0.465257 0.033 Uiso 1 1 calc R U . . .
C7 C -0.1922(2) -0.2393(2) 0.38132(14) 0.0277(3) Uani 1 1 d . . . . .
H7 H -0.229093 -0.231961 0.303039 0.033 Uiso 1 1 calc R U . . .
C8 C -0.3780(2) -0.2562(2) 0.69714(13) 0.0254(3) Uani 1 1 d . . . . .
C9 C -0.1709(2) -0.9195(2) 0.01984(14) 0.0274(3) Uani 1 1 d . . . . .
H9 H -0.093253 -0.936390 -0.042920 0.033 Uiso 1 1 calc R U . . .
C10 C -0.3748(2) -1.0451(2) 0.14896(15) 0.0293(3) Uani 1 1 d . . . . .
H10 H -0.438996 -1.146776 0.180748 0.035 Uiso 1 1 calc R U . . .
C11 C -0.4032(2) -0.8744(2) 0.19382(13) 0.0238(3) Uani 1 1 d . . . . .
C12 C -0.3015(2) -0.7249(2) 0.14582(14) 0.0254(3) Uani 1 1 d . . . . .
H12 H -0.315260 -0.607340 0.174083 0.030 Uiso 1 1 calc R U . . .
N1 N -0.18365(17) -0.74741(18) 0.05927(11) 0.0243(2) Uani 1 1 d . . . . .
N2 N -0.25907(19) -1.06927(19) 0.06200(13) 0.0309(3) Uani 1 1 d . . . . .
N3 N -0.47503(19) -0.1413(2) 0.71323(13) 0.0285(3) Uani 1 1 d . . . . .
O1 O 0.26808(17) -0.24249(19) 0.32103(11) 0.0384(3) Uani 1 1 d . . . . .
O2 O 0.01705(16) -0.30533(16) 0.18061(10) 0.0317(2) Uani 1 1 d . . . . .
O3 O 0.24906(17) -0.5285(2) 0.05617(13) 0.0346(3) Uani 1 1 d . . . . .
O4 O -0.39112(18) -0.35749(19) 0.76284(11) 0.0381(3) Uani 1 1 d . . . . .
Co1 Co 0.000000 -0.500000 0.000000 0.02186(9) Uani 1 2 d S . P . .
H03A H -0.434(3) -0.047(3) 0.6834(18) 0.033 Uiso 1 1 d . U . . .
H03B H 0.286(3) -0.486(3) 0.132(2) 0.033 Uiso 1 1 d . U . . .
H03C H 0.257(3) -0.637(3) 0.0235(18) 0.033 Uiso 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 O1 1.2446(19) . ?
C1 O2 1.2714(18) . ?
C1 C2 1.5141(18) . ?
C2 C7 1.391(2) . ?
C2 C3 1.392(2) . ?
C3 C4 1.385(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.393(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(2) . ?
C5 C8 1.4926(18) . ?
C6 C7 1.387(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 O4 1.2167(18) . ?
C8 N3 1.3700(19) . ?
C9 N2 1.329(2) . ?
C9 N1 1.3318(19) . ?
C9 H9 0.9300 . ?
C10 N2 1.3350(19) . ?
C10 C11 1.388(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.388(2) . ?
C11 N3 1.4029(18) 2_446 ?
C12 N1 1.3413(17) . ?
C12 H12 0.9300 . ?
N1 Co1 2.1863(12) . ?
N3 H03A 0.855(19) . ?
O2 Co1 2.0394(10) . ?
O3 Co1 2.1295(11) . ?
O3 H03B 0.79(2) . ?
O3 H03C 0.84(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 O2 125.52(13) . . ?
O1 C1 C2 118.90(13) . . ?
O2 C1 C2 115.57(13) . . ?
C7 C2 C3 119.35(13) . . ?
C7 C2 C1 120.38(13) . . ?
C3 C2 C1 120.24(13) . . ?
C4 C3 C2 120.12(14) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.21(13) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 119.93(13) . . ?
C6 C5 C8 122.21(13) . . ?
C4 C5 C8 117.80(13) . . ?
C7 C6 C5 119.46(13) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C6 C7 C2 120.85(13) . . ?
C6 C7 H7 119.6 . . ?
C2 C7 H7 119.6 . . ?
O4 C8 N3 122.52(13) . . ?
O4 C8 C5 121.87(13) . . ?
N3 C8 C5 115.61(12) . . ?
N2 C9 N1 125.96(13) . . ?
N2 C9 H9 117.0 . . ?
N1 C9 H9 117.0 . . ?
N2 C10 C11 122.60(13) . . ?
N2 C10 H10 118.7 . . ?
C11 C10 H10 118.7 . . ?
C10 C11 C12 116.72(13) . . ?
C10 C11 N3 119.28(13) . 2_446 ?
C12 C11 N3 123.95(13) . 2_446 ?
N1 C12 C11 120.99(13) . . ?
N1 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C9 N1 C12 117.45(12) . . ?
C9 N1 Co1 121.47(9) . . ?
C12 N1 Co1 120.84(10) . . ?
C9 N2 C10 116.22(13) . . ?
C8 N3 C11 124.42(13) . 2_446 ?
C8 N3 H03A 117.9(12) . . ?
C11 N3 H03A 114.8(12) 2_446 . ?
C1 O2 Co1 132.17(10) . . ?
Co1 O3 H03B 115.3(14) . . ?
Co1 O3 H03C 121.3(13) . . ?
H03B O3 H03C 107.9(18) . . ?
O2 Co1 O2 180.0 . 2_545 ?
O2 Co1 O3 86.19(5) . 2_545 ?
O2 Co1 O3 93.81(5) 2_545 2_545 ?
O2 Co1 O3 93.81(5) . . ?
O2 Co1 O3 86.19(5) 2_545 . ?
O3 Co1 O3 180.0 2_545 . ?
O2 Co1 N1 90.97(4) . 2_545 ?
O2 Co1 N1 89.03(4) 2_545 2_545 ?
O3 Co1 N1 90.03(5) 2_545 2_545 ?
O3 Co1 N1 89.97(5) . 2_545 ?
O2 Co1 N1 89.03(4) . . ?
O2 Co1 N1 90.97(4) 2_545 . ?
O3 Co1 N1 89.97(5) 2_545 . ?
O3 Co1 N1 90.03(5) . . ?
N1 Co1 N1 180.0 2_545 . ?

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 C7 165.09(14) . . . . ?
O2 C1 C2 C7 -14.74(19) . . . . ?
O1 C1 C2 C3 -17.1(2) . . . . ?
O2 C1 C2 C3 163.09(13) . . . . ?
C7 C2 C3 C4 1.6(2) . . . . ?
C1 C2 C3 C4 -176.21(14) . . . . ?
C2 C3 C4 C5 -2.8(2) . . . . ?
C3 C4 C5 C6 1.6(2) . . . . ?
C3 C4 C5 C8 178.77(14) . . . . ?
C4 C5 C6 C7 0.8(2) . . . . ?
C8 C5 C6 C7 -176.22(14) . . . . ?
C5 C6 C7 C2 -2.0(2) . . . . ?
C3 C2 C7 C6 0.8(2) . . . . ?
C1 C2 C7 C6 178.66(14) . . . . ?
C6 C5 C8 O4 144.97(16) . . . . ?
C4 C5 C8 O4 -32.1(2) . . . . ?
C6 C5 C8 N3 -34.8(2) . . . . ?
C4 C5 C8 N3 148.05(14) . . . . ?
N2 C10 C11 C12 -1.3(2) . . . . ?
N2 C10 C11 N3 -179.06(14) . . . 2_446 ?
C10 C11 C12 N1 0.7(2) . . . . ?
N3 C11 C12 N1 178.35(13) 2_446 . . . ?
N2 C9 N1 C12 -2.6(2) . . . . ?
N2 C9 N1 Co1 171.75(12) . . . . ?
C11 C12 N1 C9 1.1(2) . . . . ?
C11 C12 N1 Co1 -173.32(10) . . . . ?
N1 C9 N2 C10 2.1(2) . . . . ?
C11 C10 N2 C9 0.0(2) . . . . ?
O4 C8 N3 C11 0.7(2) . . . 2_446 ?
C5 C8 N3 C11 -179.53(13) . . . 2_446 ?
O1 C1 O2 Co1 46.6(2) . . . . ?
C2 C1 O2 Co1 -133.53(11) . . . . ?

_refine_diff_density_max         0.261
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_Ni2
_database_code_depnum_ccdc_archive 'CCDC 2308478'
loop_
_audit_author_name
_audit_author_address
'M. Fatima C. Guedes da Silva'
;University of Lisbon, Portugal
Portugal
;
_audit_update_record             
;
2023-11-16 deposited with the CCDC.	2024-04-25 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         'C24 H20 N6 Ni O8'
_chemical_formula_sum            'C24 H20 N6 Ni O8'
_chemical_formula_weight         579.17

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                   7.6921(2)
_cell_length_b                   7.8232(2)
_cell_length_c                   10.9612(3)
_cell_angle_alpha                108.5190(10)
_cell_angle_beta                 90.3980(10)
_cell_angle_gamma                114.6470(10)
_cell_volume                     560.99(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9433
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      26.05

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_F_000             298
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.933
_shelx_estimated_absorpt_T_min   0.754
_shelx_estimated_absorpt_T_max   0.929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.722
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22787
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.952
_diffrn_reflns_theta_max         26.086
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2228
_reflns_number_gt                2032
_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_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR-97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_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)+(0.0301P)²+0.2332P] 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         2228
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0241
_refine_ls_wR_factor_ref         0.0637
_refine_ls_wR_factor_gt          0.0614
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
C1 C -0.4071(3) 0.7279(2) 0.79068(16) 0.0251(4) Uani 1 1 d . . . . .
C2 C -0.5261(2) 0.7424(2) 0.89991(16) 0.0240(3) Uani 1 1 d . . . . .
C3 C -0.4706(3) 0.7304(3) 1.01681(17) 0.0281(4) Uani 1 1 d . . . . .
H3 H -0.355225 0.722494 1.030591 0.034 Uiso 1 1 calc R U . . .
C4 C -0.5867(3) 0.7303(3) 1.11261(17) 0.0291(4) Uani 1 1 d . . . . .
H4 H -0.551882 0.716297 1.189019 0.035 Uiso 1 1 calc R U . . .
C5 C -0.7553(2) 0.7509(3) 1.09530(16) 0.0242(3) Uani 1 1 d . . . . .
C6 C -0.8094(3) 0.7674(3) 0.97981(16) 0.0279(4) Uani 1 1 d . . . . .
H6 H -0.920904 0.783262 0.967951 0.033 Uiso 1 1 calc R U . . .
C7 C -0.6956(3) 0.7600(3) 0.88241(16) 0.0274(4) Uani 1 1 d . . . . .
H7 H -0.733716 0.766932 0.804116 0.033 Uiso 1 1 calc R U . . .
C8 C 0.1217(2) 0.7438(3) 0.20018(16) 0.0250(4) Uani 1 1 d . . . . .
C9 C -0.0971(2) 0.8754(3) 0.30992(16) 0.0226(3) Uani 1 1 d . . . . .
C10 C -0.1995(2) 0.7233(3) 0.35763(16) 0.0244(3) Uani 1 1 d . . . . .
H10 H -0.185183 0.605231 0.329530 0.029 Uiso 1 1 calc R U . . .
C11 C -0.3320(2) 0.9173(3) 0.48307(17) 0.0263(4) Uani 1 1 d . . . . .
H11 H -0.410519 0.933090 0.545635 0.032 Uiso 1 1 calc R U . . .
C12 C -0.1264(2) 1.0466(3) 0.35462(17) 0.0284(4) Uani 1 1 d . . . . .
H12 H -0.061887 1.149657 0.322844 0.034 Uiso 1 1 calc R U . . .
N1 N -0.31888(19) 0.7445(2) 0.44376(13) 0.0230(3) Uani 1 1 d . . . . .
N2 N -0.2432(2) 1.0699(2) 0.44132(15) 0.0300(3) Uani 1 1 d . . . . .
N3 N 0.0259(2) 0.8613(2) 0.21718(14) 0.0280(3) Uani 1 1 d . . . . .
O1 O -0.23908(18) 0.7505(2) 0.81563(13) 0.0360(3) Uani 1 1 d . . . . .
O2 O -0.49222(18) 0.69055(18) 0.67932(11) 0.0284(3) Uani 1 1 d . . . . .
O3 O 0.1073(2) 0.6398(2) 0.26506(13) 0.0381(3) Uani 1 1 d . . . . .
O4 O -0.25513(19) 0.4776(2) 0.55708(14) 0.0314(3) Uani 1 1 d . . . . .
Ni1 Ni -0.500000 0.500000 0.500000 0.02038(10) Uani 1 2 d S . P . .
H03A H 0.067(3) 0.961(3) 0.188(2) 0.031 Uiso 1 1 d . U . . .
H04B H -0.214(3) 0.530(3) 0.635(2) 0.031 Uiso 1 1 d . U . . .
H04A H -0.244(3) 0.374(3) 0.528(2) 0.031 Uiso 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 O1 1.246(2) . ?
C1 O2 1.267(2) . ?
C1 C2 1.516(2) . ?
C2 C7 1.385(2) . ?
C2 C3 1.391(2) . ?
C3 C4 1.383(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(2) . ?
C5 C8 1.494(2) 1_456 ?
C6 C7 1.388(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 O3 1.214(2) . ?
C8 N3 1.372(2) . ?
C9 C12 1.385(2) . ?
C9 C10 1.389(2) . ?
C9 N3 1.404(2) . ?
C10 N1 1.3422(19) . ?
C10 H10 0.9300 . ?
C11 N1 1.329(2) . ?
C11 N2 1.331(2) . ?
C11 H11 0.9300 . ?
C12 N2 1.335(2) . ?
C12 H12 0.9300 . ?
N1 Ni1 2.1257(13) . ?
N3 H03A 0.87(2) . ?
O2 Ni1 2.0376(11) . ?
O4 Ni1 2.0731(13) . ?
O4 H04B 0.81(2) . ?
O4 H04A 0.81(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 O2 125.63(15) . . ?
O1 C1 C2 118.98(15) . . ?
O2 C1 C2 115.39(15) . . ?
C7 C2 C3 119.20(14) . . ?
C7 C2 C1 120.22(15) . . ?
C3 C2 C1 120.54(15) . . ?
C4 C3 C2 120.16(16) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.37(16) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 119.74(15) . . ?
C6 C5 C8 122.04(15) . 1_456 ?
C4 C5 C8 118.14(15) . 1_456 ?
C7 C6 C5 119.39(16) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C2 C7 C6 121.07(16) . . ?
C2 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
O3 C8 N3 122.61(15) . . ?
O3 C8 C5 121.96(15) . 1_654 ?
N3 C8 C5 115.43(14) . 1_654 ?
C12 C9 C10 116.73(14) . . ?
C12 C9 N3 119.34(15) . . ?
C10 C9 N3 123.89(15) . . ?
N1 C10 C9 120.84(15) . . ?
N1 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
N1 C11 N2 126.13(15) . . ?
N1 C11 H11 116.9 . . ?
N2 C11 H11 116.9 . . ?
N2 C12 C9 122.83(16) . . ?
N2 C12 H12 118.6 . . ?
C9 C12 H12 118.6 . . ?
C11 N1 C10 117.49(14) . . ?
C11 N1 Ni1 121.42(10) . . ?
C10 N1 Ni1 120.82(11) . . ?
C11 N2 C12 115.92(15) . . ?
C8 N3 C9 124.40(14) . . ?
C8 N3 H03A 119.4(13) . . ?
C9 N3 H03A 113.5(13) . . ?
C1 O2 Ni1 130.89(11) . . ?
Ni1 O4 H04B 114.9(15) . . ?
Ni1 O4 H04A 122.2(15) . . ?
H04B O4 H04A 110(2) . . ?
O2 Ni1 O2 180.00(5) 2_466 . ?
O2 Ni1 O4 85.96(5) 2_466 . ?
O2 Ni1 O4 94.04(5) . . ?
O2 Ni1 O4 94.04(5) 2_466 2_466 ?
O2 Ni1 O4 85.96(5) . 2_466 ?
O4 Ni1 O4 180.0 . 2_466 ?
O2 Ni1 N1 91.48(5) 2_466 2_466 ?
O2 Ni1 N1 88.52(5) . 2_466 ?
O4 Ni1 N1 91.17(5) . 2_466 ?
O4 Ni1 N1 88.83(5) 2_466 2_466 ?
O2 Ni1 N1 88.52(5) 2_466 . ?
O2 Ni1 N1 91.48(5) . . ?
O4 Ni1 N1 88.83(5) . . ?
O4 Ni1 N1 91.17(5) 2_466 . ?
N1 Ni1 N1 180.0 2_466 . ?

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 C7 166.54(16) . . . . ?
O2 C1 C2 C7 -14.3(2) . . . . ?
O1 C1 C2 C3 -16.0(2) . . . . ?
O2 C1 C2 C3 163.21(16) . . . . ?
C7 C2 C3 C4 1.8(3) . . . . ?
C1 C2 C3 C4 -175.68(16) . . . . ?
C2 C3 C4 C5 -2.8(3) . . . . ?
C3 C4 C5 C6 1.4(3) . . . . ?
C3 C4 C5 C8 178.26(16) . . . 1_456 ?
C4 C5 C6 C7 1.0(3) . . . . ?
C8 C5 C6 C7 -175.78(16) 1_456 . . . ?
C3 C2 C7 C6 0.5(3) . . . . ?
C1 C2 C7 C6 178.06(16) . . . . ?
C5 C6 C7 C2 -1.9(3) . . . . ?
C12 C9 C10 N1 -0.6(2) . . . . ?
N3 C9 C10 N1 -178.20(15) . . . . ?
C10 C9 C12 N2 1.4(3) . . . . ?
N3 C9 C12 N2 179.07(16) . . . . ?
N2 C11 N1 C10 2.8(3) . . . . ?
N2 C11 N1 Ni1 -171.31(14) . . . . ?
C9 C10 N1 C11 -1.3(2) . . . . ?
C9 C10 N1 Ni1 172.85(12) . . . . ?
N1 C11 N2 C12 -2.0(3) . . . . ?
C9 C12 N2 C11 -0.2(3) . . . . ?
O3 C8 N3 C9 0.2(3) . . . . ?
C5 C8 N3 C9 179.76(15) 1_654 . . . ?
C12 C9 N3 C8 155.17(17) . . . . ?
C10 C9 N3 C8 -27.3(3) . . . . ?
O1 C1 O2 Ni1 42.2(2) . . . . ?
C2 C1 O2 Ni1 -136.90(13) . . . . ?

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.046

