# 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 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_exp_4672
_database_code_depnum_ccdc_archive 'CCDC 2295246'
loop_
_audit_author_name
_audit_author_address
'Le Wang'
;China Three Gorges University
China
;
_audit_update_record             
;
2023-09-15 deposited with the CCDC.	2023-12-11 downloaded from the CCDC.
;
_audit_creation_date             2023-06-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H6 Cl2 N Ni0.5 O3'
_chemical_formula_sum            'C9 H6 Cl2 N Ni0.50 O3'
_chemical_formula_weight         276.40
_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 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
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                   7.43760(10)
_cell_length_b                   11.9779(3)
_cell_length_c                   22.9882(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2047.95(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2842
_cell_measurement_temperature    290.15
_cell_measurement_theta_max      74.0360
_cell_measurement_theta_min      3.8510
_shelx_estimated_absorpt_T_max   0.561
_shelx_estimated_absorpt_T_min   0.244
_exptl_absorpt_coefficient_mu    6.546
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40348
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear bluish violet'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   bluish
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.793
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1112
_exptl_crystal_preparation       Solvothermal
_exptl_crystal_recrystallization_method UNK
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            5667
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.162
_diffrn_reflns_theta_min         3.846
_diffrn_ambient_temperature      290.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -7.00  54.00   0.50    4.14    --    0.00  38.00 -90.00  122
  2  ω     58.00  83.00   0.50    4.14    --    0.00  38.00 -90.00   50
  3  ω    -13.00  31.00   0.50    4.14    --    0.00 -82.00  60.00   88
  4  ω      7.00  98.00   0.50   16.57    --   95.80 -45.00   0.00  182
  5  ω     89.00 116.00   0.50   16.57    --   95.80  82.00-120.00   54
  6  ω    127.00 171.00   0.50   16.57    --   95.80  82.00-120.00   88
  7  ω      6.00  99.00   0.50   16.57    --   95.80 -61.00 -90.00  186
  8  ω     74.00  99.00   0.50   16.57    --   95.80 -45.00 150.00   50
  9  ω     41.00  68.00   0.50   16.57    --   95.80 -45.00 150.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0453460000
_diffrn_orient_matrix_UB_12      -0.1139528000
_diffrn_orient_matrix_UB_13      0.0272890000
_diffrn_orient_matrix_UB_21      -0.1395475000
_diffrn_orient_matrix_UB_22      -0.0212279000
_diffrn_orient_matrix_UB_23      -0.0482557000
_diffrn_orient_matrix_UB_31      0.1462792000
_diffrn_orient_matrix_UB_32      -0.0556793000
_diffrn_orient_matrix_UB_33      -0.0376432000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1667
_reflns_number_total             2015
_reflns_odcompleteness_completeness 99.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         2015
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0441
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0593P)²+1.0257P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1163
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Rotating group:
 O1(H1a,H1b)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C1(H1), C2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.750000 0.250000 0.27910(2) 0.0180(2) Uani 1 2 d S T P . .
Cl2 Cl 0.42189(10) 0.48655(7) 0.39113(3) 0.0344(2) Uani 1 1 d . . . . .
Cl1 Cl 0.32381(10) 0.37303(8) 0.50934(3) 0.0370(2) Uani 1 1 d . . . . .
O2 O 0.5236(2) 0.34956(18) 0.27341(8) 0.0230(4) Uani 1 1 d . . . . .
O1 O 0.6067(2) 0.10458(18) 0.28106(8) 0.0248(5) Uani 1 1 d . . . . .
H1A H 0.506658 0.113763 0.263593 0.037 Uiso 1 1 d R U . . .
H1B H 0.661008 0.055163 0.260926 0.037 Uiso 1 1 d R U . . .
O3 O 0.2448(2) 0.4002(2) 0.25188(9) 0.0321(5) Uani 1 1 d . . . . .
N2 N 0.750000 0.250000 0.37392(13) 0.0216(7) Uani 1 2 d S T P . .
N1 N 0.750000 0.250000 0.68405(14) 0.0256(8) Uani 1 2 d S T P . .
C8 C 0.2942(3) 0.3008(2) 0.33974(11) 0.0179(6) Uani 1 1 d . . . . .
C7 C 0.3589(3) 0.3537(2) 0.28361(11) 0.0180(6) Uani 1 1 d . . . . .
C6 C 0.8170(4) 0.3356(3) 0.40454(12) 0.0259(6) Uani 1 1 d . . . . .
H6 H 0.863878 0.396230 0.384299 0.031 Uiso 1 1 calc R U . . .
C4 C 0.750000 0.250000 0.49645(16) 0.0242(9) Uani 1 2 d S T P . .
C10 C 0.2864(3) 0.3038(3) 0.44478(12) 0.0238(6) Uani 1 1 d . . . . .
C9 C 0.3287(3) 0.3549(3) 0.39242(12) 0.0210(6) Uani 1 1 d . . . . .
C3 C 0.750000 0.250000 0.56121(17) 0.0256(9) Uani 1 2 d S T P . .
C5 C 0.8202(4) 0.3385(3) 0.46497(12) 0.0281(7) Uani 1 1 d . . . . .
H5 H 0.869244 0.399674 0.484206 0.034 Uiso 1 1 calc R U . . .
C1 C 0.8858(4) 0.2934(3) 0.65335(12) 0.0333(8) Uani 1 1 d . . . . .
H1 H 0.982504 0.323932 0.673472 0.040 Uiso 1 1 calc R U . . .
C2 C 0.8899(4) 0.2951(3) 0.59304(12) 0.0331(8) Uani 1 1 d . . . . .
H2 H 0.987548 0.326751 0.573884 0.040 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
Ni1 O2 2.0674(18) . ?
Ni1 O2 2.0674(18) 2_655 ?
Ni1 O1 2.042(2) 2_655 ?
Ni1 O1 2.042(2) . ?
Ni1 N2 2.180(3) . ?
Ni1 N1 2.185(3) 7_565 ?
Cl2 C9 1.723(3) . ?
Cl1 C10 1.723(3) . ?
O2 C7 1.248(3) . ?
O1 H1A 0.8529 . ?
O1 H1B 0.8530 . ?
O3 C7 1.250(3) . ?
N2 C6 1.340(3) 2_655 ?
N2 C6 1.340(3) . ?
N1 C1 1.337(3) 2_655 ?
N1 C1 1.337(3) . ?
C8 C8 1.383(5) 2 ?
C8 C7 1.516(3) . ?
C8 C9 1.397(4) . ?
C6 H6 0.9300 . ?
C6 C5 1.390(4) . ?
C4 C3 1.489(5) . ?
C4 C5 1.386(4) . ?
C4 C5 1.386(4) 2_655 ?
C10 C10 1.398(6) 2 ?
C10 C9 1.386(4) . ?
C3 C2 1.382(4) 2_655 ?
C3 C2 1.382(4) . ?
C5 H5 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.387(4) . ?
C2 H2 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
O2 Ni1 O2 172.75(11) . 2_655 ?
O2 Ni1 N2 93.63(5) . . ?
O2 Ni1 N2 93.63(5) 2_655 . ?
O2 Ni1 N1 86.37(5) 2_655 7_565 ?
O2 Ni1 N1 86.37(5) . 7_565 ?
O1 Ni1 O2 86.24(8) 2_655 . ?
O1 Ni1 O2 93.92(8) . . ?
O1 Ni1 O2 86.24(8) . 2_655 ?
O1 Ni1 O2 93.92(8) 2_655 2_655 ?
O1 Ni1 O1 177.47(11) 2_655 . ?
O1 Ni1 N2 88.73(5) . . ?
O1 Ni1 N2 88.74(5) 2_655 . ?
O1 Ni1 N1 91.26(5) 2_655 7_565 ?
O1 Ni1 N1 91.27(5) . 7_565 ?
N2 Ni1 N1 180.0 . 7_565 ?
C7 O2 Ni1 144.1(2) . . ?
Ni1 O1 H1A 109.6 . . ?
Ni1 O1 H1B 109.4 . . ?
H1A O1 H1B 104.3 . . ?
C6 N2 Ni1 121.68(16) 2_655 . ?
C6 N2 Ni1 121.68(16) . . ?
C6 N2 C6 116.6(3) 2_655 . ?
C1 N1 Ni1 121.85(16) . 7_566 ?
C1 N1 Ni1 121.85(16) 2_655 7_566 ?
C1 N1 C1 116.3(3) 2_655 . ?
C8 C8 C7 121.25(15) 2 . ?
C8 C8 C9 119.69(16) 2 . ?
C9 C8 C7 119.1(2) . . ?
O2 C7 O3 125.1(3) . . ?
O2 C7 C8 117.0(2) . . ?
O3 C7 C8 117.9(2) . . ?
N2 C6 H6 118.3 . . ?
N2 C6 C5 123.4(3) . . ?
C5 C6 H6 118.3 . . ?
C5 C4 C3 121.47(18) 2_655 . ?
C5 C4 C3 121.48(18) . . ?
C5 C4 C5 117.0(4) 2_655 . ?
C10 C10 Cl1 120.42(11) 2 . ?
C9 C10 Cl1 119.9(2) . . ?
C9 C10 C10 119.64(17) . 2 ?
C8 C9 Cl2 118.9(2) . . ?
C10 C9 Cl2 120.7(2) . . ?
C10 C9 C8 120.4(3) . . ?
C2 C3 C4 121.97(17) . . ?
C2 C3 C4 121.97(17) 2_655 . ?
C2 C3 C2 116.1(3) . 2_655 ?
C6 C5 H5 120.1 . . ?
C4 C5 C6 119.8(3) . . ?
C4 C5 H5 120.1 . . ?
N1 C1 H1 118.3 . . ?
N1 C1 C2 123.4(3) . . ?
C2 C1 H1 118.3 . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?

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 O2 C7 O3 -142.7(3) . . . . ?
Ni1 O2 C7 C8 39.1(4) . . . . ?
Ni1 N2 C6 C5 -179.7(2) . . . . ?
Ni1 N1 C1 C2 -179.8(3) 7_566 . . . ?
Cl1 C10 C9 Cl2 1.0(3) . . . . ?
Cl1 C10 C9 C8 -178.2(2) . . . . ?
N2 C6 C5 C4 -0.6(4) . . . . ?
N1 C1 C2 C3 -0.4(5) . . . . ?
C8 C8 C7 O2 -104.9(4) 2 . . . ?
C8 C8 C7 O3 76.7(4) 2 . . . ?
C8 C8 C9 Cl2 -174.6(3) 2 . . . ?
C8 C8 C9 C10 4.6(5) 2 . . . ?
C7 C8 C9 Cl2 6.9(3) . . . . ?
C7 C8 C9 C10 -173.9(2) . . . . ?
C6 N2 C6 C5 0.3(2) 2_655 . . . ?
C4 C3 C2 C1 -179.8(2) . . . . ?
C10 C10 C9 Cl2 -179.0(3) 2 . . . ?
C10 C10 C9 C8 1.8(5) 2 . . . ?
C9 C8 C7 O2 73.6(3) . . . . ?
C9 C8 C7 O3 -104.7(3) . . . . ?
C3 C4 C5 C6 -179.7(2) . . . . ?
C5 C4 C3 C2 143.6(2) 2_655 . . . ?
C5 C4 C3 C2 -36.4(2) 2_655 . . 2_655 ?
C5 C4 C3 C2 -36.4(2) . . . . ?
C5 C4 C3 C2 143.6(2) . . . 2_655 ?
C5 C4 C5 C6 0.3(2) 2_655 . . . ?
C1 N1 C1 C2 0.2(3) 2_655 . . . ?
C2 C3 C2 C1 0.2(2) 2_655 . . . ?

_olex2_exptl_crystal_mounting_method GLASS
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.870
_oxdiff_exptl_absorpt_empirical_full_min 0.187
