# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_hd_2_2_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2131730'
loop_
_audit_author_name
_audit_author_address
'Mrinal Kanti Adak'
;IIT Delhi
India
;
_audit_update_record             
;
2022-08-10 deposited with the CCDC.	2022-08-15 downloaded from the CCDC.
;
_audit_creation_date             2022-08-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_chemical_name_common            ?
_chemical_name_systematic        C8H7ClN3Ni0.5O0.5
_chemical_formula_moiety         'C8 H7 Cl N3 Ni0.5, 0.5(O)'
_chemical_formula_sum            'C8 H7 Cl N3 Ni0.50 O0.50'
_chemical_formula_weight         217.97
_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 0.0033 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'
Cl Cl 0.1484 0.1585 '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      orthorhombic
_space_group_IT_number           52
_space_group_name_H-M_alt        'P n n a'
_space_group_name_Hall           '-P 2a 2bc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 'x, -y+1/2, -z+1/2'
3 '-x+1/2, y+1/2, -z+1/2'
4 '-x+1/2, -y, z'
5 '-x, -y, -z'
6 '-x, y-1/2, z-1/2'
7 'x-1/2, -y-1/2, z-1/2'
8 'x-1/2, y, -z'

_cell_length_a                   9.07(6)
_cell_length_b                   15.98(11)
_cell_length_c                   12.33(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1786(21)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2888
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      30.5750
_cell_measurement_theta_min      2.9910
_exptl_absorpt_coefficient_mu    1.404
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51021
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'clear bluish blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   bluish
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.1391
_diffrn_reflns_av_unetI/netI     0.0907
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14443
_diffrn_reflns_theta_full        27.37
_diffrn_reflns_theta_max         27.37
_diffrn_reflns_theta_min         2.09
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1056
_reflns_number_total             2022
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 97-2 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         2022
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1349
_refine_ls_R_factor_gt           0.0530
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0418P)²+1.0898P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1255
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C8(H8), C1(H1), C7(H7), C2(H2), C3(H3A), C4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.56168(8) 0.7500 0.2500 0.0388(3) Uani 1 2 d S . .
Cl1 Cl 0.37989(12) 0.63911(7) 0.26566(9) 0.0486(3) Uani 1 1 d . . .
N1 N 0.7283(4) 0.6620(2) 0.2877(3) 0.0426(9) Uani 1 1 d . . .
N2 N 0.5813(4) 0.7669(2) 0.4119(3) 0.0423(9) Uani 1 1 d . . .
N3 N 0.6913(4) 0.7336(2) 0.5631(3) 0.0550(11) Uani 1 1 d . . .
H3 H 0.7484 0.7085 0.6083 0.066 Uiso 1 1 calc R . .
C6 C 0.6811(5) 0.7175(3) 0.4566(4) 0.0435(11) Uani 1 1 d . . .
C5 C 0.7649(5) 0.6597(3) 0.3920(4) 0.0482(12) Uani 1 1 d . . .
C8 C 0.5274(5) 0.8159(3) 0.4920(4) 0.0544(13) Uani 1 1 d . . .
H8 H 0.4549 0.8566 0.4837 0.065 Uiso 1 1 calc R . .
C1 C 0.7992(5) 0.6110(3) 0.2201(4) 0.0548(13) Uani 1 1 d . . .
H1 H 0.7740 0.6115 0.1470 0.066 Uiso 1 1 calc R . .
C7 C 0.5965(5) 0.7959(3) 0.5870(4) 0.0588(14) Uani 1 1 d . . .
H7 H 0.5813 0.8204 0.6546 0.071 Uiso 1 1 calc R . .
C2 C 0.9090(5) 0.5575(3) 0.2548(5) 0.0673(15) Uani 1 1 d . . .
H2 H 0.9568 0.5225 0.2059 0.081 Uiso 1 1 calc R . .
C3 C 0.9462(6) 0.5567(3) 0.3617(5) 0.0673(15) Uani 1 1 d . . .
H3A H 1.0210 0.5219 0.3865 0.081 Uiso 1 1 calc R . .
C4 C 0.8718(5) 0.6080(3) 0.4324(4) 0.0588(14) Uani 1 1 d . . .
H4 H 0.8937 0.6076 0.5061 0.071 Uiso 1 1 calc R . .
O1 O 0.2500 0.5000 0.0809(7) 0.180(4) Uani 1 2 d S . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ni1 0.0395(5) 0.0407(4) 0.0362(5) 0.0007(4) 0.000 0.000
Cl1 0.0482(7) 0.0465(6) 0.0510(7) 0.0001(6) 0.0073(6) -0.0029(5)
N1 0.042(2) 0.041(2) 0.045(2) -0.0027(18) 0.0021(18) 0.0019(18)
N2 0.042(2) 0.044(2) 0.041(2) -0.0015(17) -0.0046(18) 0.0022(18)
N3 0.050(3) 0.067(3) 0.048(3) 0.000(2) -0.013(2) 0.007(2)
C6 0.044(3) 0.041(3) 0.045(3) 0.003(2) -0.008(2) -0.003(2)
C5 0.044(3) 0.039(3) 0.062(3) 0.000(2) -0.002(3) 0.004(2)
C8 0.050(3) 0.061(3) 0.053(3) -0.006(3) -0.003(3) 0.007(2)
C1 0.057(3) 0.049(3) 0.059(3) 0.000(3) 0.004(3) -0.001(3)
C7 0.056(4) 0.075(4) 0.045(3) -0.017(3) -0.005(3) 0.016(3)
C2 0.062(3) 0.049(3) 0.091(5) 0.000(3) 0.019(4) 0.010(3)
C3 0.067(4) 0.060(3) 0.075(4) 0.004(3) -0.004(3) 0.018(3)
C4 0.053(3) 0.055(3) 0.068(4) 0.007(3) -0.012(3) 0.008(3)
O1 0.224(9) 0.126(7) 0.190(9) 0.000 0.000 0.026(7)

_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 Cl1 2.428(11) 2_565 ?
Ni1 Cl1 2.428(11) . ?
Ni1 N1 2.116(10) . ?
Ni1 N1 2.116(10) 2_565 ?
Ni1 N2 2.022(14) 2_565 ?
Ni1 N2 2.022(14) . ?
N1 C5 1.329(10) . ?
N1 C1 1.330(8) . ?
N2 C6 1.321(8) . ?
N2 C8 1.352(8) . ?
N3 H3 0.8600 . ?
N3 C6 1.341(10) . ?
N3 C7 1.349(8) . ?
C6 C5 1.437(8) . ?
C5 C4 1.368(8) . ?
C8 H8 0.9300 . ?
C8 C7 1.366(10) . ?
C1 H1 0.9300 . ?
C1 C2 1.380(9) . ?
C7 H7 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.359(11) . ?
C3 H3A 0.9300 . ?
C3 C4 1.373(9) . ?
C4 H4 0.9300 . ?

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
Cl1 Ni1 Cl1 94.5(5) . 2_565 ?
N1 Ni1 Cl1 170.93(12) . 2_565 ?
N1 Ni1 Cl1 170.93(12) 2_565 . ?
N1 Ni1 Cl1 89.0(5) 2_565 2_565 ?
N1 Ni1 Cl1 89.0(5) . . ?
N1 Ni1 N1 88.9(5) 2_565 . ?
N2 Ni1 Cl1 94.50(15) 2_565 2_565 ?
N2 Ni1 Cl1 92.35(14) 2_565 . ?
N2 Ni1 Cl1 92.35(14) . 2_565 ?
N2 Ni1 Cl1 94.50(15) . . ?
N2 Ni1 N1 93.7(2) . 2_565 ?
N2 Ni1 N1 79.0(2) 2_565 2_565 ?
N2 Ni1 N1 93.7(2) 2_565 . ?
N2 Ni1 N1 79.0(2) . . ?
N2 Ni1 N2 169.9(2) . 2_565 ?
C5 N1 Ni1 114.2(3) . . ?
C5 N1 C1 117.9(5) . . ?
C1 N1 Ni1 128.0(5) . . ?
C6 N2 Ni1 113.1(4) . . ?
C6 N2 C8 106.8(6) . . ?
C8 N2 Ni1 140.0(4) . . ?
C6 N3 H3 125.9 . . ?
C6 N3 C7 108.2(4) . . ?
C7 N3 H3 125.9 . . ?
N2 C6 N3 110.0(5) . . ?
N2 C6 C5 121.0(6) . . ?
N3 C6 C5 129.0(5) . . ?
N1 C5 C6 112.7(5) . . ?
N1 C5 C4 123.1(5) . . ?
C4 C5 C6 124.2(6) . . ?
N2 C8 H8 125.5 . . ?
N2 C8 C7 109.0(6) . . ?
C7 C8 H8 125.5 . . ?
N1 C1 H1 118.9 . . ?
N1 C1 C2 122.3(6) . . ?
C2 C1 H1 118.9 . . ?
N3 C7 C8 106.1(5) . . ?
N3 C7 H7 127.0 . . ?
C8 C7 H7 127.0 . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 119.0(5) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3A 120.4 . . ?
C2 C3 C4 119.2(6) . . ?
C4 C3 H3A 120.4 . . ?
C5 C4 C3 118.5(6) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?

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 N1 C5 C6 0.6(5) . . . . ?
Ni1 N1 C5 C4 -178.9(4) . . . . ?
Ni1 N1 C1 C2 178.4(3) . . . . ?
Ni1 N2 C6 N3 178.3(3) . . . . ?
Ni1 N2 C6 C5 0.7(5) . . . . ?
Ni1 N2 C8 C7 -176.7(4) . . . . ?
Cl1 Ni1 N1 C5 -95.0(4) . . . . ?
Cl1 Ni1 N1 C5 17.4(9) 2_565 . . . ?
Cl1 Ni1 N1 C1 85.8(4) . . . . ?
Cl1 Ni1 N1 C1 -161.7(5) 2_565 . . . ?
Cl1 Ni1 N2 C6 87.9(6) . . . . ?
Cl1 Ni1 N2 C6 -177.5(3) 2_565 . . . ?
Cl1 Ni1 N2 C8 -0.6(5) 2_565 . . . ?
Cl1 Ni1 N2 C8 -95.3(7) . . . . ?
N1 Ni1 N1 C5 93.8(4) 2_565 . . . ?
N1 Ni1 N1 C1 -85.3(4) 2_565 . . . ?
N1 Ni1 N2 C6 -0.2(3) . . . . ?
N1 Ni1 N2 C6 -88.3(6) 2_565 . . . ?
N1 Ni1 N2 C8 88.5(7) 2_565 . . . ?
N1 Ni1 N2 C8 176.6(5) . . . . ?
N1 C5 C4 C3 0.8(8) . . . . ?
N1 C1 C2 C3 -0.1(7) . . . . ?
N2 Ni1 N1 C5 -0.2(3) . . . . ?
N2 Ni1 N1 C5 172.7(3) 2_565 . . . ?
N2 Ni1 N1 C1 -179.4(4) . . . . ?
N2 Ni1 N1 C1 -6.4(4) 2_565 . . . ?
N2 Ni1 N2 C6 -44.7(4) 2_565 . . . ?
N2 Ni1 N2 C8 132.1(5) 2_565 . . . ?
N2 C6 C5 N1 -0.9(6) . . . . ?
N2 C6 C5 C4 178.6(4) . . . . ?
N2 C8 C7 N3 -0.7(6) . . . . ?
N3 C6 C5 N1 -178.0(4) . . . . ?
N3 C6 C5 C4 1.5(8) . . . . ?
C6 N2 C8 C7 0.2(5) . . . . ?
C6 N3 C7 C8 1.0(6) . . . . ?
C6 C5 C4 C3 -178.7(5) . . . . ?
C5 N1 C1 C2 -0.7(7) . . . . ?
C8 N2 C6 N3 0.4(5) . . . . ?
C8 N2 C6 C5 -177.2(4) . . . . ?
C1 N1 C5 C6 179.8(4) . . . . ?
C1 N1 C5 C4 0.3(7) . . . . ?
C1 C2 C3 C4 1.2(8) . . . . ?
C7 N3 C6 N2 -0.9(5) . . . . ?
C7 N3 C6 C5 176.5(5) . . . . ?
C2 C3 C4 C5 -1.5(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
