# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_20211121li_lidz3105_0m
_database_code_depnum_ccdc_archive 'CCDC 2181192'
loop_
_audit_author_name
_audit_author_address
'Hengcong  Huang'
;Tongji University
China
;
_audit_update_record             
;
2022-06-22 deposited with the CCDC.	2023-06-23 downloaded from the CCDC.
;
_audit_creation_date             2021-11-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H6 N4 Ni O2'
_chemical_formula_sum            'C8 H6 N4 Ni O2'
_chemical_formula_weight         248.88
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -1.3357 3.2904 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           127
_space_group_name_H-M_alt        'P 4/m b m'
_space_group_name_Hall           '-P 4 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-y, x, z'
'y, -x, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'y+1/2, x+1/2, -z'
'-y+1/2, -x+1/2, -z'
'-x, -y, -z'
'x, y, -z'
'y, -x, -z'
'-y, x, -z'
'x-1/2, -y-1/2, z'
'-x-1/2, y-1/2, z'
'-y-1/2, -x-1/2, z'
'y-1/2, x-1/2, z'

_cell_length_a                   13.4433(11)
_cell_length_b                   13.4433(11)
_cell_length_c                   7.1126(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1285.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3048
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      59.13
_cell_measurement_theta_min      4.05
_shelx_estimated_absorpt_T_max   0.495
_shelx_estimated_absorpt_T_min   0.440
_exptl_absorpt_coefficient_mu    8.192
_exptl_absorpt_correction_T_max  0.7518
_exptl_absorpt_correction_T_min  0.6033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1283 before and 0.0608 after correction.
The Ratio of minimum to maximum transmission is 0.8025.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9875
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.139
_diffrn_reflns_theta_min         4.046
_diffrn_ambient_temperature      300.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Metaljet PHOTON III'
_diffrn_measurement_method       'ω and φ shutterless scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   MetalJet
_diffrn_source_current           2.86
_diffrn_source_power             0.19937059999999998
_diffrn_source_type              'Liquid Metal source'
_diffrn_source_voltage           69.71
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                685
_reflns_number_total             834
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2019)'
_computing_data_collection       'Bruker BIS V6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     55
_refine_ls_number_reflns         834
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0371
_refine_ls_restrained_S_all      1.107
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0606P)²+0.4043P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1057
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Shared sites
{N2, N2A}
3. Uiso/Uaniso restraints and constraints
Uanis(N2) = Uanis(N2A)
4. Others
 Fixed Sof: N2(0.25) C5(0.5) H5(0.5) C4(0.5) H4(0.5) N2A(0.25)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.10046(3) 0.60046(3) 0.500000 0.0239(2) Uani 1 4 d S T P . .
O1 O 0.36256(17) 0.25232(16) 0.500000 0.0336(6) Uani 1 2 d S T P . .
N1 N 0.1179(2) 0.4514(2) 0.500000 0.0284(6) Uani 1 2 d S T P A .
N2 N 0.10345(15) 0.60345(15) 0.1952(4) 0.0340(7) Uani 0.5 2 d S T P A 1
C3 C 0.2721(2) 0.2279(2) 0.500000 0.0291(10) Uani 1 4 d S T P . .
C2 C 0.1949(2) 0.3051(2) 0.500000 0.0282(9) Uani 1 4 d S T P A .
C1 C 0.2073(3) 0.4070(2) 0.500000 0.0350(8) Uani 1 2 d S T P . .
H1 H 0.268148 0.439797 0.500000 0.042 Uiso 1 2 calc R U P A .
C5 C 0.1789(5) 0.5849(6) 0.0976(8) 0.0571(18) Uani 0.5 1 d . . P . .
H5 H 0.238117 0.570285 0.159450 0.069 Uiso 0.5 1 calc R U P A 1
C4 C 0.1291(6) 0.5192(5) 0.0967(8) 0.0528(16) Uani 0.5 1 d . . P . .
H4 H 0.146613 0.461688 0.161530 0.063 Uiso 0.5 1 calc R U P A 1
N2A N 0.10345(15) 0.60345(15) 0.1952(4) 0.0340(7) Uani 0.5 2 d S T P A 2


_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 O1 2.101(2) 5_556 ?
Ni1 O1 2.101(2) 11_566 ?
Ni1 N1 2.018(3) 7_456 ?
Ni1 N1 2.018(3) . ?
Ni1 N2 2.169(3) . ?
Ni1 N2 2.169(3) 10_556 ?
Ni1 C3 2.423(5) 11_566 ?
Ni1 N2A 2.169(3) . ?
O1 C3 1.260(3) . ?
N1 N1 1.316(6) 15_665 ?
N1 C1 1.342(4) . ?
N2 C5 1.254(6) 16_565 ?
N2 C5 1.254(6) . ?
N2 C4 1.376(6) 16_565 ?
N2 C4 1.376(6) . ?
C3 C2 1.467(6) . ?
C2 C1 1.380(4) 15_665 ?
C2 C1 1.380(4) . ?
C1 H1 0.9300 . ?
C5 C5 1.389(12) 10 ?
C5 H5 0.9300 . ?
C5 C4 1.772(8) 10 ?
C5 N2A 1.254(6) . ?
C4 C4 1.376(11) 10 ?
C4 H4 0.9300 . ?
C4 N2A 1.376(6) . ?

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 Ni1 O1 62.62(13) 5_556 11_566 ?
O1 Ni1 N2 88.72(7) 5_556 10_556 ?
O1 Ni1 N2 88.72(7) 11_566 10_556 ?
O1 Ni1 N2 88.72(7) 11_566 . ?
O1 Ni1 N2 88.72(7) 5_556 . ?
O1 Ni1 C3 31.31(6) 11_566 11_566 ?
O1 Ni1 C3 31.31(7) 5_556 11_566 ?
O1 Ni1 N2A 88.72(7) 11_566 . ?
O1 Ni1 N2A 88.72(7) 5_556 . ?
N1 Ni1 O1 97.03(9) 7_456 5_556 ?
N1 Ni1 O1 159.66(11) . 5_556 ?
N1 Ni1 O1 159.66(11) 7_456 11_566 ?
N1 Ni1 O1 97.03(9) . 11_566 ?
N1 Ni1 N1 103.31(16) 7_456 . ?
N1 Ni1 N2 90.93(5) 7_456 . ?
N1 Ni1 N2 90.93(5) . 10_556 ?
N1 Ni1 N2 90.93(5) 7_456 10_556 ?
N1 Ni1 N2 90.93(5) . . ?
N1 Ni1 C3 128.34(8) 7_456 11_566 ?
N1 Ni1 C3 128.34(8) . 11_566 ?
N1 Ni1 N2A 90.93(5) 7_456 . ?
N1 Ni1 N2A 90.93(5) . . ?
N2 Ni1 N2 177.00(16) 10_556 . ?
N2 Ni1 C3 88.50(8) . 11_566 ?
N2 Ni1 C3 88.50(8) 10_556 11_566 ?
N2A Ni1 C3 88.50(8) . 11_566 ?
C3 O1 Ni1 88.6(2) . 3_655 ?
N1 N1 Ni1 128.34(8) 15_665 . ?
N1 N1 C1 108.6(2) 15_665 . ?
C1 N1 Ni1 123.1(2) . . ?
C5 N2 Ni1 124.4(3) . . ?
C5 N2 Ni1 124.4(3) 16_565 . ?
C5 N2 C5 90.9(6) 16_565 . ?
C5 N2 C4 115.7(4) 16_565 . ?
C5 N2 C4 49.6(4) 16_565 16_565 ?
C5 N2 C4 115.7(4) . 16_565 ?
C5 N2 C4 49.6(4) . . ?
C4 N2 Ni1 119.9(3) 16_565 . ?
C4 N2 Ni1 119.9(3) . . ?
C4 N2 C4 98.8(6) 16_565 . ?
O1 C3 Ni1 60.1(2) 15_665 3_655 ?
O1 C3 Ni1 60.1(2) . 3_655 ?
O1 C3 O1 120.2(4) 15_665 . ?
O1 C3 C2 119.9(2) 15_665 . ?
O1 C3 C2 119.9(2) . . ?
C2 C3 Ni1 180.0(3) . 3_655 ?
C1 C2 C3 128.1(2) 15_665 . ?
C1 C2 C3 128.1(2) . . ?
C1 C2 C1 103.8(4) 15_665 . ?
N1 C1 C2 109.5(3) . . ?
N1 C1 H1 125.2 . . ?
C2 C1 H1 125.2 . . ?
N2 C5 C5 123.6(3) . 10 ?
N2 C5 H5 118.2 . . ?
N2 C5 C4 103.0(5) . 10 ?
C5 C5 H5 118.2 10 . ?
C5 C5 C4 38.7(3) 10 10 ?
C4 C5 H5 126.0 10 . ?
N2A C5 C5 123.6(3) . 10 ?
N2A C5 C4 103.0(5) . 10 ?
N2 C4 C4 120.6(3) . 10 ?
N2 C4 H4 119.7 . . ?
C4 C4 H4 119.7 10 . ?
N2A C4 C4 120.6(3) . 10 ?
C5 N2A Ni1 124.4(3) 16_565 . ?
C5 N2A Ni1 124.4(3) . . ?
C5 N2A C5 90.9(6) 16_565 . ?
C5 N2A C4 115.7(4) . 16_565 ?
C5 N2A C4 49.6(4) 16_565 16_565 ?
C5 N2A C4 49.6(4) . . ?
C5 N2A C4 115.7(4) 16_565 . ?
C4 N2A Ni1 119.9(3) . . ?
C4 N2A Ni1 119.9(3) 16_565 . ?
C4 N2A C4 98.8(6) 16_565 . ?

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
Ni1 O1 C3 O1 0.0 3_655 . . 15_665 ?
Ni1 O1 C3 C2 180.0 3_655 . . . ?
Ni1 N1 C1 C2 180.0 . . . . ?
Ni1 N2 C5 C5 178.45(8) . . . 10 ?
Ni1 N2 C5 C4 142.3(3) . . . 10 ?
Ni1 N2 C4 C4 178.47(8) . . . 10 ?
O1 C3 C2 C1 0.0 15_665 . . 15_665 ?
O1 C3 C2 C1 180.0 . . . 15_665 ?
O1 C3 C2 C1 180.0 15_665 . . . ?
O1 C3 C2 C1 0.0 . . . . ?
N1 N1 C1 C2 0.0 15_665 . . . ?
C3 C2 C1 N1 180.0 . . . . ?
C1 C2 C1 N1 0.0 15_665 . . . ?
C5 N2 C5 C5 -47.6(6) 16_565 . . 10 ?
C5 N2 C5 C4 -83.7(6) 16_565 . . 10 ?
C5 N2 C4 C4 -2.9(7) 16_565 . . 10 ?
C5 N2 C4 C4 -70.1(4) . . . 10 ?
C5 C5 N2A Ni1 178.45(8) 10 . . . ?
C5 C5 N2A C5 -47.6(6) 10 . . 16_565 ?
C5 C5 N2A C4 76.3(4) 10 . . . ?
C5 C5 N2A C4 -3.0(7) 10 . . 16_565 ?
C4 N2 C5 C5 -3.0(7) 16_565 . . 10 ?
C4 N2 C5 C5 76.3(4) . . . 10 ?
C4 N2 C5 C4 40.2(4) . . . 10 ?
C4 N2 C5 C4 -39.1(7) 16_565 . . 10 ?
C4 N2 C4 C4 46.3(5) 16_565 . . 10 ?
C4 C5 N2A Ni1 142.3(3) 10 . . . ?
C4 C5 N2A C5 -83.7(6) 10 . . 16_565 ?
C4 C5 N2A C4 -39.1(7) 10 . . 16_565 ?
C4 C5 N2A C4 40.2(4) 10 . . . ?
C4 C4 N2A Ni1 178.47(8) 10 . . . ?
C4 C4 N2A C5 -70.1(4) 10 . . . ?
C4 C4 N2A C5 -2.9(7) 10 . . 16_565 ?
C4 C4 N2A C4 46.3(5) 10 . . 16_565 ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.484 -0.148 -0.093 497.9 99.8 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
