# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_Ni(AIN)2
_database_code_depnum_ccdc_archive 'CCDC 2192392'
loop_
_audit_author_name
_audit_author_address
'Chang Seop Hong'
;Korea University
South Korea
;
_audit_update_record             
;
2022-08-29 deposited with the CCDC.	2022-11-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 N4 Ni O4'
_chemical_formula_weight         332.95

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 0.0064 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3447 1.0913 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           34
_space_group_name_H-M_alt        'P n n 2'
_space_group_name_Hall           'P 2 -2n'

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

_cell_length_a                   11.985(2)
_cell_length_b                   6.8910(14)
_cell_length_c                   10.624(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     877.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    18456
_cell_measurement_theta_min      0.401
_cell_measurement_theta_max      33.749

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_F_000             340
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.039
_exptl_crystal_size_mid          0.037
_exptl_crystal_size_min          0.035
_exptl_absorpt_coefficient_mu    1.073
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.926
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.700
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9439
_diffrn_reflns_av_unetI/netI     0.0639
_diffrn_reflns_av_R_equivalents  0.0792
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.523
_diffrn_reflns_theta_max         33.280
_diffrn_reflns_theta_full        24.835
_diffrn_measured_fraction_theta_max 0.855
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.855
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.834
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2963
_reflns_number_gt                1813
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.868
_reflns_Friedel_fraction_max     0.811
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'PAL BL2D-SMDC Program (Shin et. al, 2016)'
_computing_cell_refinement       'HKL3000sm (Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    WingX
_computing_publication_material  WingX
_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)+(0.1147P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 681 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.251(11)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2963
_refine_ls_number_parameters     96
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0590
_refine_ls_wR_factor_ref         0.1976
_refine_ls_wR_factor_gt          0.1746
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.024
_refine_ls_shift/su_mean         0.001

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
C2 C 0.2831(6) 0.1149(11) 0.4110(7) 0.0576(17) Uani 1 1 d . . . . .
H2 H 0.257826 0.044765 0.340651 0.069 Uiso 1 1 calc R U . . .
C3 C 0.2420(5) 0.3027(10) 0.4332(6) 0.0488(13) Uani 1 1 d . . . . .
C4 C 0.2879(6) 0.4093(10) 0.5332(7) 0.0523(15) Uani 1 1 d . . . . .
C5 C 0.3677(5) 0.3146(10) 0.6084(6) 0.0549(17) Uani 1 1 d . . . . .
H5 H 0.399571 0.384626 0.675294 0.066 Uiso 1 1 calc R U . . .
C6 C 0.1540(5) 0.3832(10) 0.3493(6) 0.0485(14) Uani 1 1 d . . . . .
Ni1 Ni 0.500000 0.000000 0.7202(2) 0.0429(3) Uani 1 2 d S T P . .
O1 O 0.1122(3) 0.2792(6) 0.2619(4) 0.0468(10) Uani 1 1 d . . . . .
N1 N 0.4012(4) 0.1311(9) 0.5908(5) 0.0487(12) Uani 1 1 d . . . . .
C1 C 0.3596(6) 0.0328(10) 0.4907(8) 0.0529(17) Uani 1 1 d . . . . .
H1 H 0.383795 -0.094788 0.475558 0.063 Uiso 1 1 calc R U . . .
O2 O 0.1197(4) 0.5567(8) 0.3646(4) 0.0536(12) Uani 1 1 d . . . . .
N2 N 0.2582(6) 0.5904(10) 0.5620(6) 0.074(2) Uani 1 1 d . . . . .
H2A H 0.207535 0.649449 0.517589 0.089 Uiso 1 1 calc R U . . .
H2B H 0.289519 0.649465 0.625126 0.089 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 C1 1.370(10) . ?
C2 C3 1.404(9) . ?
C2 H2 0.9400 . ?
C3 C4 1.404(10) . ?
C3 C6 1.488(9) . ?
C4 N2 1.333(10) . ?
C4 C5 1.407(9) . ?
C5 N1 1.340(8) . ?
C5 H5 0.9400 . ?
C6 O2 1.274(8) . ?
C6 O1 1.276(8) . ?
C6 Ni1 2.436(6) 3_454 ?
Ni1 N1 2.027(5) . ?
Ni1 N1 2.027(5) 2_655 ?
Ni1 O1 2.078(4) 3 ?
Ni1 O1 2.078(4) 4_545 ?
Ni1 O2 2.137(5) 3 ?
Ni1 O2 2.137(5) 4_545 ?
N1 C1 1.357(9) . ?
C1 H1 0.9400 . ?
N2 H2A 0.8700 . ?
N2 H2B 0.8700 . ?

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
C1 C2 C3 120.7(6) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 118.2(6) . . ?
C4 C3 C6 122.4(6) . . ?
C2 C3 C6 119.5(6) . . ?
N2 C4 C3 124.0(6) . . ?
N2 C4 C5 119.0(6) . . ?
C3 C4 C5 116.9(6) . . ?
N1 C5 C4 124.2(6) . . ?
N1 C5 H5 117.9 . . ?
C4 C5 H5 117.9 . . ?
O2 C6 O1 119.5(6) . . ?
O2 C6 C3 120.1(6) . . ?
O1 C6 C3 120.3(6) . . ?
O2 C6 Ni1 61.2(3) . 3_454 ?
O1 C6 Ni1 58.5(3) . 3_454 ?
C3 C6 Ni1 175.7(5) . 3_454 ?
N1 Ni1 N1 94.6(3) . 2_655 ?
N1 Ni1 O1 101.29(19) . 3 ?
N1 Ni1 O1 95.34(19) 2_655 3 ?
N1 Ni1 O1 95.34(19) . 4_545 ?
N1 Ni1 O1 101.29(19) 2_655 4_545 ?
O1 Ni1 O1 155.4(3) 3 4_545 ?
N1 Ni1 O2 163.9(2) . 3 ?
N1 Ni1 O2 90.8(2) 2_655 3 ?
O1 Ni1 O2 63.03(19) 3 3 ?
O1 Ni1 O2 98.49(19) 4_545 3 ?
N1 Ni1 O2 90.8(2) . 4_545 ?
N1 Ni1 O2 163.9(2) 2_655 4_545 ?
O1 Ni1 O2 98.49(19) 3 4_545 ?
O1 Ni1 O2 63.03(19) 4_545 4_545 ?
O2 Ni1 O2 88.2(3) 3 4_545 ?
N1 Ni1 C6 132.6(2) . 3 ?
N1 Ni1 C6 95.0(2) 2_655 3 ?
O1 Ni1 C6 31.59(19) 3 3 ?
O1 Ni1 C6 127.7(2) 4_545 3 ?
O2 Ni1 C6 31.5(2) 3 3 ?
O2 Ni1 C6 92.5(2) 4_545 3 ?
N1 Ni1 C6 95.0(2) . 4_545 ?
N1 Ni1 C6 132.6(2) 2_655 4_545 ?
O1 Ni1 C6 127.7(2) 3 4_545 ?
O1 Ni1 C6 31.59(19) 4_545 4_545 ?
O2 Ni1 C6 92.5(2) 3 4_545 ?
O2 Ni1 C6 31.5(2) 4_545 4_545 ?
C6 Ni1 C6 111.5(3) 3 4_545 ?
C6 O1 Ni1 89.9(4) . 3_454 ?
C5 N1 C1 118.0(6) . . ?
C5 N1 Ni1 120.1(4) . . ?
C1 N1 Ni1 121.6(5) . . ?
N1 C1 C2 121.7(6) . . ?
N1 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
C6 O2 Ni1 87.3(4) . 3_454 ?
C4 N2 H2A 120.0 . . ?
C4 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?

_refine_diff_density_max         0.787
_refine_diff_density_min         -1.726
_refine_diff_density_rms         0.093




