# 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 2021

####################################################################### 
# 
# 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_RJ-E-49
_database_code_depnum_ccdc_archive 'CCDC 2074093'
loop_
_audit_author_name
_audit_author_address
'Dr. Rajesh G. Gonnade'
;CSIR NATIONAL CHEMICAL LABORATORY PUNE 
India
;
_audit_update_record             
;
2021-03-29 deposited with the CCDC.	2021-05-31 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         'C15 H20 Cl N3 Ni O2'
_chemical_formula_sum            'C15 H20 Cl N3 Ni O2'
_chemical_formula_weight         368.50

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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   16.793(3)
_cell_length_b                   9.9261(18)
_cell_length_c                   19.198(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3200.2(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1269
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      29.33

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_F_000             1536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.041
_exptl_absorpt_coefficient_mu    1.389
_shelx_estimated_absorpt_T_min   0.819
_shelx_estimated_absorpt_T_max   0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.819
_exptl_absorpt_correction_T_max  0.945
_exptl_absorpt_process_details   'SADABS (BRUKER, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            41734
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.609
_diffrn_reflns_theta_max         30.015
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4658
_reflns_number_gt                4192
_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_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL, Mercury 2020.20'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0225P)²+2.1977P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4658
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0231
_refine_ls_wR_factor_ref         0.0575
_refine_ls_wR_factor_gt          0.0552
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.004
_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
Ni1 Ni 0.57044(2) 0.75412(2) 0.37395(2) 0.00860(4) Uani 1 1 d . . . . .
Cl1 Cl 0.67435(2) 0.80535(3) 0.43875(2) 0.01341(6) Uani 1 1 d . . . . .
O1 O 0.53809(5) 0.35840(8) 0.41605(4) 0.01387(16) Uani 1 1 d . . . . .
O2 O 0.38644(5) 0.81277(9) 0.24840(4) 0.01611(16) Uani 1 1 d . . . . .
N1 N 0.57774(6) 0.57037(9) 0.39638(5) 0.01048(17) Uani 1 1 d . . . . .
N2 N 0.46781(6) 0.72912(9) 0.33696(5) 0.01009(17) Uani 1 1 d . . . . .
N3 N 0.56669(5) 0.93190(10) 0.33069(5) 0.01106(17) Uani 1 1 d . . . . .
C1 C 0.65270(7) 0.49175(11) 0.39666(6) 0.0128(2) Uani 1 1 d . . . . .
H1A H 0.692018 0.531091 0.429256 0.015 Uiso 1 1 calc R U . . .
H1B H 0.676388 0.487396 0.349491 0.015 Uiso 1 1 calc R U . . .
C2 C 0.62556(7) 0.35260(11) 0.42111(6) 0.0144(2) Uani 1 1 d . . . . .
H2A H 0.647350 0.280975 0.390696 0.017 Uiso 1 1 calc R U . . .
H2B H 0.642645 0.335496 0.469663 0.017 Uiso 1 1 calc R U . . .
C3 C 0.51914(7) 0.48783(11) 0.40409(5) 0.01023(19) Uani 1 1 d . . . . .
C4 C 0.43492(6) 0.52222(11) 0.40011(6) 0.01024(19) Uani 1 1 d . . . . .
C5 C 0.37857(7) 0.43465(11) 0.42950(6) 0.0128(2) Uani 1 1 d . . . . .
H5 H 0.395641 0.352853 0.450407 0.015 Uiso 1 1 calc R U . . .
C6 C 0.29825(7) 0.46644(12) 0.42829(6) 0.0152(2) Uani 1 1 d . . . . .
H6 H 0.260170 0.406936 0.448097 0.018 Uiso 1 1 calc R U . . .
C7 C 0.27407(7) 0.58715(13) 0.39756(6) 0.0158(2) Uani 1 1 d . . . . .
H7 H 0.219269 0.610882 0.397855 0.019 Uiso 1 1 calc R U . . .
C8 C 0.32887(7) 0.67310(12) 0.36655(6) 0.0134(2) Uani 1 1 d . . . . .
H8 H 0.310877 0.753839 0.345149 0.016 Uiso 1 1 calc R U . . .
C9 C 0.41087(7) 0.64221(11) 0.36639(5) 0.01018(19) Uani 1 1 d . . . . .
C10 C 0.44698(7) 0.81502(11) 0.28465(5) 0.01088(19) Uani 1 1 d . . . . .
C11 C 0.51082(7) 0.91881(11) 0.27090(6) 0.0130(2) Uani 1 1 d . . . . .
H11A H 0.541096 0.892812 0.228746 0.016 Uiso 1 1 calc R U . . .
H11B H 0.485474 1.007130 0.261826 0.016 Uiso 1 1 calc R U . . .
C12 C 0.53757(7) 1.03764(12) 0.38023(6) 0.0156(2) Uani 1 1 d . . . . .
H12A H 0.535318 1.124805 0.355241 0.019 Uiso 1 1 calc R U . . .
H12B H 0.576917 1.047061 0.418314 0.019 Uiso 1 1 calc R U . . .
C13 C 0.45631(8) 1.01039(14) 0.41225(7) 0.0227(3) Uani 1 1 d . . . . .
H13A H 0.416365 1.003466 0.375216 0.034 Uiso 1 1 calc R U . . .
H13B H 0.442156 1.084395 0.443692 0.034 Uiso 1 1 calc R U . . .
H13C H 0.458064 0.925751 0.438491 0.034 Uiso 1 1 calc R U . . .
C14 C 0.64639(7) 0.97862(12) 0.30357(6) 0.0159(2) Uani 1 1 d . . . . .
H14A H 0.680209 1.004796 0.343576 0.019 Uiso 1 1 calc R U . . .
H14B H 0.638216 1.059815 0.274486 0.019 Uiso 1 1 calc R U . . .
C15 C 0.69023(8) 0.87345(14) 0.26079(7) 0.0217(3) Uani 1 1 d . . . . .
H15A H 0.659567 0.853107 0.218647 0.033 Uiso 1 1 calc R U . . .
H15B H 0.696660 0.791175 0.288437 0.033 Uiso 1 1 calc R U . . .
H15C H 0.742752 0.908205 0.247672 0.033 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 N1 1.8780(10) . ?
Ni1 N2 1.8806(10) . ?
Ni1 N3 1.9514(10) . ?
Ni1 Cl1 2.2025(4) . ?
O1 C3 1.3434(13) . ?
O1 C2 1.4733(14) . ?
O2 C10 1.2323(14) . ?
N1 C3 1.2890(14) . ?
N1 C1 1.4811(14) . ?
N2 C10 1.3630(14) . ?
N2 C9 1.4064(14) . ?
N3 C11 1.4880(14) . ?
N3 C12 1.4984(15) . ?
N3 C14 1.5091(15) . ?
C1 C2 1.5283(16) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.4570(15) . ?
C4 C5 1.4033(15) . ?
C4 C9 1.4145(15) . ?
C5 C6 1.3854(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.3959(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.3889(16) . ?
C7 H7 0.9500 . ?
C8 C9 1.4107(16) . ?
C8 H8 0.9500 . ?
C10 C11 1.5101(16) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.5209(18) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.5187(18) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
N1 Ni1 N2 91.05(4) . . ?
N1 Ni1 N3 167.95(4) . . ?
N2 Ni1 N3 85.93(4) . . ?
N1 Ni1 Cl1 92.46(3) . . ?
N2 Ni1 Cl1 165.90(3) . . ?
N3 Ni1 Cl1 93.28(3) . . ?
C3 O1 C2 106.55(8) . . ?
C3 N1 C1 108.27(9) . . ?
C3 N1 Ni1 126.43(8) . . ?
C1 N1 Ni1 124.61(7) . . ?
C10 N2 C9 120.35(9) . . ?
C10 N2 Ni1 115.52(7) . . ?
C9 N2 Ni1 123.53(7) . . ?
C11 N3 C12 110.18(9) . . ?
C11 N3 C14 108.65(9) . . ?
C12 N3 C14 107.05(9) . . ?
C11 N3 Ni1 105.64(7) . . ?
C12 N3 Ni1 111.95(7) . . ?
C14 N3 Ni1 113.33(7) . . ?
N1 C1 C2 102.94(9) . . ?
N1 C1 H1A 111.2 . . ?
C2 C1 H1A 111.2 . . ?
N1 C1 H1B 111.2 . . ?
C2 C1 H1B 111.2 . . ?
H1A C1 H1B 109.1 . . ?
O1 C2 C1 103.99(9) . . ?
O1 C2 H2A 111.0 . . ?
C1 C2 H2A 111.0 . . ?
O1 C2 H2B 111.0 . . ?
C1 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
N1 C3 O1 116.53(10) . . ?
N1 C3 C4 125.89(10) . . ?
O1 C3 C4 117.58(9) . . ?
C5 C4 C9 120.86(10) . . ?
C5 C4 C3 119.24(10) . . ?
C9 C4 C3 119.89(10) . . ?
C6 C5 C4 120.57(11) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 119.07(11) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C8 C7 C6 121.04(11) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 120.94(11) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
N2 C9 C8 122.09(10) . . ?
N2 C9 C4 120.42(10) . . ?
C8 C9 C4 117.43(10) . . ?
O2 C10 N2 128.05(10) . . ?
O2 C10 C11 119.97(10) . . ?
N2 C10 C11 111.92(9) . . ?
N3 C11 C10 111.86(9) . . ?
N3 C11 H11A 109.2 . . ?
C10 C11 H11A 109.2 . . ?
N3 C11 H11B 109.2 . . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
N3 C12 C13 115.14(10) . . ?
N3 C12 H12A 108.5 . . ?
C13 C12 H12A 108.5 . . ?
N3 C12 H12B 108.5 . . ?
C13 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C15 113.91(10) . . ?
N3 C14 H14A 108.8 . . ?
C15 C14 H14A 108.8 . . ?
N3 C14 H14B 108.8 . . ?
C15 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
N2 Ni1 N1 C3 -21.00(10) . . . . ?
N3 Ni1 N1 C3 -96.3(2) . . . . ?
Cl1 Ni1 N1 C3 145.34(9) . . . . ?
N2 Ni1 N1 C1 148.34(9) . . . . ?
N3 Ni1 N1 C1 73.1(2) . . . . ?
Cl1 Ni1 N1 C1 -45.33(8) . . . . ?
N1 Ni1 N2 C10 -150.51(8) . . . . ?
N3 Ni1 N2 C10 17.82(8) . . . . ?
Cl1 Ni1 N2 C10 105.06(13) . . . . ?
N1 Ni1 N2 C9 38.35(9) . . . . ?
N3 Ni1 N2 C9 -153.33(9) . . . . ?
Cl1 Ni1 N2 C9 -66.08(16) . . . . ?
C3 N1 C1 C2 -11.31(11) . . . . ?
Ni1 N1 C1 C2 177.72(7) . . . . ?
C3 O1 C2 C1 -10.34(11) . . . . ?
N1 C1 C2 O1 12.76(11) . . . . ?
C1 N1 C3 O1 5.33(13) . . . . ?
Ni1 N1 C3 O1 176.10(7) . . . . ?
C1 N1 C3 C4 -173.85(10) . . . . ?
Ni1 N1 C3 C4 -3.08(16) . . . . ?
C2 O1 C3 N1 3.55(13) . . . . ?
C2 O1 C3 C4 -177.20(9) . . . . ?
N1 C3 C4 C5 -160.97(11) . . . . ?
O1 C3 C4 C5 19.85(15) . . . . ?
N1 C3 C4 C9 19.54(16) . . . . ?
O1 C3 C4 C9 -159.63(10) . . . . ?
C9 C4 C5 C6 -2.36(16) . . . . ?
C3 C4 C5 C6 178.16(10) . . . . ?
C4 C5 C6 C7 -0.17(17) . . . . ?
C5 C6 C7 C8 1.97(17) . . . . ?
C6 C7 C8 C9 -1.25(17) . . . . ?
C10 N2 C9 C8 -26.69(15) . . . . ?
Ni1 N2 C9 C8 144.04(9) . . . . ?
C10 N2 C9 C4 156.29(10) . . . . ?
Ni1 N2 C9 C4 -32.97(14) . . . . ?
C7 C8 C9 N2 -178.33(10) . . . . ?
C7 C8 C9 C4 -1.23(16) . . . . ?
C5 C4 C9 N2 -179.84(10) . . . . ?
C3 C4 C9 N2 -0.37(15) . . . . ?
C5 C4 C9 C8 3.01(15) . . . . ?
C3 C4 C9 C8 -177.51(10) . . . . ?
C9 N2 C10 O2 -14.88(17) . . . . ?
Ni1 N2 C10 O2 173.67(10) . . . . ?
C9 N2 C10 C11 167.90(9) . . . . ?
Ni1 N2 C10 C11 -3.55(12) . . . . ?
C12 N3 C11 C10 -90.45(11) . . . . ?
C14 N3 C11 C10 152.57(9) . . . . ?
Ni1 N3 C11 C10 30.65(10) . . . . ?
O2 C10 C11 N3 163.61(10) . . . . ?
N2 C10 C11 N3 -18.92(13) . . . . ?
C11 N3 C12 C13 60.69(13) . . . . ?
C14 N3 C12 C13 178.67(10) . . . . ?
Ni1 N3 C12 C13 -56.55(12) . . . . ?
C11 N3 C14 C15 -69.66(12) . . . . ?
C12 N3 C14 C15 171.38(10) . . . . ?
Ni1 N3 C14 C15 47.45(11) . . . . ?

_refine_diff_density_max         0.456
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_RJ-D-57
_database_code_depnum_ccdc_archive 'CCDC 2074094'
loop_
_audit_author_name
_audit_author_address
'Dr. Rajesh G. Gonnade'
;CSIR NATIONAL CHEMICAL LABORATORY PUNE 
India
;
_audit_update_record             
;
2021-03-29 deposited with the CCDC.	2021-05-31 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         'C22 H26 Cl N3 Ni O2'
_chemical_formula_sum            'C22 H26 Cl N3 Ni O2'
_chemical_formula_weight         458.62

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'
Cl Cl 0.1484 0.1585 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   9.9695(4)
_cell_length_b                   10.0137(3)
_cell_length_c                   21.4431(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2140.70(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9954
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      33.71

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    1.054
_shelx_estimated_absorpt_T_min   0.809
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.809
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_process_details   'SADABS (BRUKER, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            44424
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.245
_diffrn_reflns_theta_max         34.629
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             8381
_reflns_number_gt                7601
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_max     0.870
_reflns_Friedel_fraction_full    0.998

_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_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL, Mercury 2020.20'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0258P)²+0.1125P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_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 2969 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.008(4)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         8381
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_ref         0.0585
_refine_ls_wR_factor_gt          0.0557
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_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
Ni1 Ni 0.25618(2) 0.40663(2) 0.32600(2) 0.01826(5) Uani 1 1 d . . . . .
Cl1 Cl 0.16288(4) 0.36065(4) 0.41591(2) 0.02700(8) Uani 1 1 d . . . . .
O1 O 0.11418(14) 0.77763(11) 0.28691(6) 0.0313(3) Uani 1 1 d . . . . .
O2 O 0.50115(13) 0.36073(13) 0.18309(6) 0.0331(3) Uani 1 1 d . . . . .
N1 N 0.17822(13) 0.57870(11) 0.32468(6) 0.0208(2) Uani 1 1 d . . . . .
N2 N 0.31927(14) 0.42599(12) 0.24374(6) 0.0208(2) Uani 1 1 d . . . . .
N3 N 0.35873(13) 0.23954(12) 0.32755(6) 0.0220(2) Uani 1 1 d . . . . .
C1 C 0.15427(17) 0.66305(14) 0.38113(7) 0.0228(3) Uani 1 1 d . . . . .
H1 H 0.093755 0.616220 0.411213 0.027 Uiso 1 1 calc R U . . .
C2 C 0.0847(2) 0.78517(18) 0.35328(8) 0.0342(4) Uani 1 1 d . . . . .
H2A H -0.013225 0.781697 0.360776 0.041 Uiso 1 1 calc R U . . .
H2AB H 0.120802 0.868595 0.371497 0.041 Uiso 1 1 calc R U . . .
C3 C 0.15930(17) 0.65248(14) 0.27638(7) 0.0235(3) Uani 1 1 d . . . . .
C4 C 0.17979(17) 0.61551(15) 0.21190(7) 0.0240(3) Uani 1 1 d . . . . .
C5 C 0.11833(19) 0.69150(17) 0.16500(8) 0.0318(4) Uani 1 1 d . . . . .
H5 H 0.066997 0.767859 0.176022 0.038 Uiso 1 1 calc R U . . .
C6 C 0.1315(2) 0.6568(2) 0.10303(9) 0.0378(4) Uani 1 1 d . . . . .
H6 H 0.090517 0.709043 0.071349 0.045 Uiso 1 1 calc R U . . .
C7 C 0.2054(2) 0.5444(2) 0.08784(8) 0.0363(4) Uani 1 1 d . . . . .
H7 H 0.213290 0.518696 0.045353 0.044 Uiso 1 1 calc R U . . .
C8 C 0.2679(2) 0.46888(17) 0.13319(7) 0.0292(3) Uani 1 1 d . . . . .
H8 H 0.318311 0.392439 0.121354 0.035 Uiso 1 1 calc R U . . .
C9 C 0.25828(18) 0.50327(13) 0.19656(7) 0.0223(3) Uani 1 1 d . . . . .
C10 C 0.42945(17) 0.35259(15) 0.22965(7) 0.0234(3) Uani 1 1 d . . . . .
C11 C 0.46589(18) 0.25349(16) 0.27985(8) 0.0269(3) Uani 1 1 d . . . . .
H11A H 0.482817 0.165363 0.260462 0.032 Uiso 1 1 calc R U . . .
H11B H 0.549772 0.282685 0.300462 0.032 Uiso 1 1 calc R U . . .
C12 C 0.26831(19) 0.12340(14) 0.31194(8) 0.0283(3) Uani 1 1 d . . . . .
H12A H 0.197804 0.117187 0.344326 0.034 Uiso 1 1 calc R U . . .
H12B H 0.321843 0.040234 0.313863 0.034 Uiso 1 1 calc R U . . .
C13 C 0.2012(2) 0.13080(19) 0.24876(9) 0.0368(4) Uani 1 1 d . . . . .
H13A H 0.269768 0.134051 0.216070 0.055 Uiso 1 1 calc R U . . .
H13B H 0.145552 0.211367 0.246583 0.055 Uiso 1 1 calc R U . . .
H13C H 0.144655 0.051770 0.242713 0.055 Uiso 1 1 calc R U . . .
C14 C 0.42417(19) 0.20465(17) 0.38872(8) 0.0294(4) Uani 1 1 d . . . . .
H14A H 0.483797 0.126837 0.382173 0.035 Uiso 1 1 calc R U . . .
H14B H 0.353557 0.177418 0.418584 0.035 Uiso 1 1 calc R U . . .
C15 C 0.5054(2) 0.3165(2) 0.41761(10) 0.0409(4) Uani 1 1 d . . . . .
H15A H 0.577803 0.342236 0.389135 0.061 Uiso 1 1 calc R U . . .
H15B H 0.543799 0.286112 0.457201 0.061 Uiso 1 1 calc R U . . .
H15C H 0.447054 0.393626 0.425172 0.061 Uiso 1 1 calc R U . . .
C16 C 0.28924(16) 0.69333(15) 0.41118(8) 0.0233(3) Uani 1 1 d . . . . .
H16A H 0.329277 0.608611 0.426002 0.028 Uiso 1 1 calc R U . . .
H16B H 0.349865 0.730982 0.379114 0.028 Uiso 1 1 calc R U . . .
C17 C 0.28139(16) 0.78989(14) 0.46539(7) 0.0222(3) Uani 1 1 d . . . . .
C18 C 0.1890(2) 0.77469(17) 0.51320(8) 0.0312(4) Uani 1 1 d . . . . .
H18 H 0.125649 0.703911 0.511350 0.037 Uiso 1 1 calc R U . . .
C19 C 0.1876(2) 0.86170(19) 0.56394(9) 0.0366(4) Uani 1 1 d . . . . .
H19 H 0.123237 0.850911 0.596212 0.044 Uiso 1 1 calc R U . . .
C20 C 0.2807(2) 0.96379(17) 0.56693(8) 0.0334(4) Uani 1 1 d . . . . .
H20 H 0.282692 1.021295 0.602151 0.040 Uiso 1 1 calc R U . . .
C21 C 0.37074(19) 0.98233(16) 0.51885(9) 0.0310(4) Uani 1 1 d . . . . .
H21 H 0.433095 1.053985 0.520503 0.037 Uiso 1 1 calc R U . . .
C22 C 0.37031(16) 0.89638(15) 0.46806(8) 0.0249(3) Uani 1 1 d . . . . .
H22 H 0.431539 0.910611 0.434770 0.030 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 N2 1.8826(12) . ?
Ni1 N1 1.8904(12) . ?
Ni1 N3 1.9611(12) . ?
Ni1 Cl1 2.1896(4) . ?
O1 C3 1.3505(18) . ?
O1 C2 1.455(2) . ?
O2 C10 1.2306(19) . ?
N1 C3 1.2862(19) . ?
N1 C1 1.4953(19) . ?
N2 C10 1.356(2) . ?
N2 C9 1.4114(19) . ?
N3 C11 1.486(2) . ?
N3 C14 1.506(2) . ?
N3 C12 1.509(2) . ?
C1 C16 1.522(2) . ?
C1 C2 1.527(2) . ?
C1 H1 1.0000 . ?
C2 H2A 0.9900 . ?
C2 H2AB 0.9900 . ?
C3 C4 1.446(2) . ?
C4 C5 1.402(2) . ?
C4 C9 1.408(2) . ?
C5 C6 1.380(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.384(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.380(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.405(2) . ?
C8 H8 0.9500 . ?
C10 C11 1.509(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.513(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.515(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.514(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.387(2) . ?
C17 C22 1.388(2) . ?
C18 C19 1.394(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.382(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.379(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.388(2) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?

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
N2 Ni1 N1 91.69(5) . . ?
N2 Ni1 N3 85.96(5) . . ?
N1 Ni1 N3 172.85(6) . . ?
N2 Ni1 Cl1 171.32(4) . . ?
N1 Ni1 Cl1 91.73(4) . . ?
N3 Ni1 Cl1 91.55(4) . . ?
C3 O1 C2 106.20(13) . . ?
C3 N1 C1 107.70(11) . . ?
C3 N1 Ni1 126.58(10) . . ?
C1 N1 Ni1 124.64(10) . . ?
C10 N2 C9 119.11(13) . . ?
C10 N2 Ni1 115.07(10) . . ?
C9 N2 Ni1 125.74(11) . . ?
C11 N3 C14 108.05(13) . . ?
C11 N3 C12 110.45(13) . . ?
C14 N3 C12 105.85(12) . . ?
C11 N3 Ni1 106.44(9) . . ?
C14 N3 Ni1 116.01(10) . . ?
C12 N3 Ni1 110.02(10) . . ?
N1 C1 C16 108.30(13) . . ?
N1 C1 C2 102.02(13) . . ?
C16 C1 C2 114.04(14) . . ?
N1 C1 H1 110.7 . . ?
C16 C1 H1 110.7 . . ?
C2 C1 H1 110.7 . . ?
O1 C2 C1 104.43(13) . . ?
O1 C2 H2A 110.9 . . ?
C1 C2 H2A 110.9 . . ?
O1 C2 H2AB 110.9 . . ?
C1 C2 H2AB 110.9 . . ?
H2A C2 H2AB 108.9 . . ?
N1 C3 O1 116.56(14) . . ?
N1 C3 C4 127.03(13) . . ?
O1 C3 C4 116.40(13) . . ?
C5 C4 C9 120.55(15) . . ?
C5 C4 C3 119.03(15) . . ?
C9 C4 C3 120.41(14) . . ?
C6 C5 C4 120.82(17) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 118.83(16) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C8 C7 C6 121.34(17) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C9 121.07(16) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C8 C9 C4 117.35(14) . . ?
C8 C9 N2 121.96(14) . . ?
C4 C9 N2 120.63(13) . . ?
O2 C10 N2 128.00(15) . . ?
O2 C10 C11 118.85(15) . . ?
N2 C10 C11 113.12(14) . . ?
N3 C11 C10 112.33(13) . . ?
N3 C11 H11A 109.1 . . ?
C10 C11 H11A 109.1 . . ?
N3 C11 H11B 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
N3 C12 C13 115.16(13) . . ?
N3 C12 H12A 108.5 . . ?
C13 C12 H12A 108.5 . . ?
N3 C12 H12B 108.5 . . ?
C13 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C15 114.59(14) . . ?
N3 C14 H14A 108.6 . . ?
C15 C14 H14A 108.6 . . ?
N3 C14 H14B 108.6 . . ?
C15 C14 H14B 108.6 . . ?
H14A C14 H14B 107.6 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C1 113.98(13) . . ?
C17 C16 H16A 108.8 . . ?
C1 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
C1 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C18 C17 C22 118.57(14) . . ?
C18 C17 C16 122.13(14) . . ?
C22 C17 C16 119.30(14) . . ?
C17 C18 C19 120.99(16) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C20 C19 C18 119.47(17) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C21 C20 C19 120.12(16) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 120.06(16) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C17 C22 C21 120.71(15) . . ?
C17 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?

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
N2 Ni1 N1 C3 12.98(14) . . . . ?
Cl1 Ni1 N1 C3 -159.04(14) . . . . ?
N2 Ni1 N1 C1 -153.65(12) . . . . ?
Cl1 Ni1 N1 C1 34.34(12) . . . . ?
N1 Ni1 N2 C10 153.65(12) . . . . ?
N3 Ni1 N2 C10 -19.58(12) . . . . ?
N1 Ni1 N2 C9 -29.69(13) . . . . ?
N3 Ni1 N2 C9 157.07(13) . . . . ?
C3 N1 C1 C16 -106.75(15) . . . . ?
Ni1 N1 C1 C16 62.01(15) . . . . ?
C3 N1 C1 C2 13.86(17) . . . . ?
Ni1 N1 C1 C2 -177.39(12) . . . . ?
C3 O1 C2 C1 15.0(2) . . . . ?
N1 C1 C2 O1 -17.14(18) . . . . ?
C16 C1 C2 O1 99.38(16) . . . . ?
C1 N1 C3 O1 -5.07(19) . . . . ?
Ni1 N1 C3 O1 -173.55(11) . . . . ?
C1 N1 C3 C4 175.61(17) . . . . ?
Ni1 N1 C3 C4 7.1(3) . . . . ?
C2 O1 C3 N1 -6.8(2) . . . . ?
C2 O1 C3 C4 172.62(16) . . . . ?
N1 C3 C4 C5 161.32(18) . . . . ?
O1 C3 C4 C5 -18.0(2) . . . . ?
N1 C3 C4 C9 -17.5(3) . . . . ?
O1 C3 C4 C9 163.20(15) . . . . ?
C9 C4 C5 C6 1.1(3) . . . . ?
C3 C4 C5 C6 -177.69(18) . . . . ?
C4 C5 C6 C7 0.7(3) . . . . ?
C5 C6 C7 C8 -1.4(3) . . . . ?
C6 C7 C8 C9 0.2(3) . . . . ?
C7 C8 C9 C4 1.5(3) . . . . ?
C7 C8 C9 N2 178.76(17) . . . . ?
C5 C4 C9 C8 -2.2(2) . . . . ?
C3 C4 C9 C8 176.60(16) . . . . ?
C5 C4 C9 N2 -179.45(16) . . . . ?
C3 C4 C9 N2 -0.7(2) . . . . ?
C10 N2 C9 C8 26.8(2) . . . . ?
Ni1 N2 C9 C8 -149.69(14) . . . . ?
C10 N2 C9 C4 -156.03(15) . . . . ?
Ni1 N2 C9 C4 27.4(2) . . . . ?
C9 N2 C10 O2 14.3(3) . . . . ?
Ni1 N2 C10 O2 -168.77(15) . . . . ?
C9 N2 C10 C11 -167.65(14) . . . . ?
Ni1 N2 C10 C11 9.24(18) . . . . ?
C14 N3 C11 C10 -149.88(13) . . . . ?
C12 N3 C11 C10 94.77(16) . . . . ?
Ni1 N3 C11 C10 -24.63(16) . . . . ?
O2 C10 C11 N3 -170.54(15) . . . . ?
N2 C10 C11 N3 11.3(2) . . . . ?
C11 N3 C12 C13 -57.84(19) . . . . ?
C14 N3 C12 C13 -174.56(15) . . . . ?
Ni1 N3 C12 C13 59.38(17) . . . . ?
C11 N3 C14 C15 69.60(18) . . . . ?
C12 N3 C14 C15 -172.06(16) . . . . ?
Ni1 N3 C14 C15 -49.75(19) . . . . ?
N1 C1 C16 C17 174.16(12) . . . . ?
C2 C1 C16 C17 61.35(18) . . . . ?
C1 C16 C17 C18 48.5(2) . . . . ?
C1 C16 C17 C22 -132.29(15) . . . . ?
C22 C17 C18 C19 -2.0(3) . . . . ?
C16 C17 C18 C19 177.22(17) . . . . ?
C17 C18 C19 C20 -0.7(3) . . . . ?
C18 C19 C20 C21 2.5(3) . . . . ?
C19 C20 C21 C22 -1.6(3) . . . . ?
C18 C17 C22 C21 2.8(2) . . . . ?
C16 C17 C22 C21 -176.36(15) . . . . ?
C20 C21 C22 C17 -1.1(3) . . . . ?

_refine_diff_density_max         0.254
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_RJ-E-04
_database_code_depnum_ccdc_archive 'CCDC 2074095'
loop_
_audit_author_name
_audit_author_address
'Dr. Rajesh G. Gonnade'
;CSIR NATIONAL CHEMICAL LABORATORY PUNE 
India
;
_audit_update_record             
;
2021-03-29 deposited with the CCDC.	2021-05-31 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         'C19 H28 Cl N3 Ni O2'
_chemical_formula_sum            'C19 H28 Cl N3 Ni O2'
_chemical_formula_weight         424.60

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'
Cl Cl 0.1484 0.1585 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   9.7315(3)
_cell_length_b                   9.8437(3)
_cell_length_c                   21.1840(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2029.30(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9376
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      30.49

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.105
_shelx_estimated_absorpt_T_min   0.809
_shelx_estimated_absorpt_T_max   0.947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.809
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_process_details   'SADABS (BRUKER, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            36549
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.281
_diffrn_reflns_theta_max         30.523
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6183
_reflns_number_gt                6036
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.773
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.996

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL, Mercury 2020.20'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0206P)²+0.3822P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.023(8)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         6183
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0193
_refine_ls_R_factor_gt           0.0187
_refine_ls_wR_factor_ref         0.0483
_refine_ls_wR_factor_gt          0.0481
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_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
Ni1 Ni 0.22247(2) 0.50447(2) 0.41595(2) 0.01362(4) Uani 1 1 d . . . . .
Cl1 Cl 0.17719(4) 0.39489(4) 0.32813(2) 0.01889(7) Uani 1 1 d . . . . .
O1 O 0.59048(12) 0.34352(12) 0.46643(5) 0.0205(2) Uani 1 1 d . . . . .
O2 O 0.16657(14) 0.77065(12) 0.55320(6) 0.0266(3) Uani 1 1 d . . . . .
N1 N 0.39679(12) 0.42115(12) 0.42206(6) 0.0156(2) Uani 1 1 d . . . . .
N2 N 0.23733(13) 0.57837(12) 0.49781(6) 0.0155(2) Uani 1 1 d . . . . .
N3 N 0.05306(13) 0.61048(13) 0.40888(6) 0.0188(2) Uani 1 1 d . . . . .
C1 C 0.48546(15) 0.38150(16) 0.36782(7) 0.0169(3) Uani 1 1 d . . . . .
H1 H 0.433630 0.321279 0.338184 0.020 Uiso 1 1 calc R U . . .
C2 C 0.59969(17) 0.30132(17) 0.40091(8) 0.0230(3) Uani 1 1 d . . . . .
H2A H 0.584335 0.202295 0.396771 0.028 Uiso 1 1 calc R U . . .
H2AB H 0.690768 0.324133 0.382984 0.028 Uiso 1 1 calc R U . . .
C3 C 0.46577(15) 0.40197(15) 0.47329(7) 0.0163(3) Uani 1 1 d . . . . .
C4 C 0.42274(16) 0.43320(15) 0.53703(7) 0.0169(3) Uani 1 1 d . . . . .
C5 C 0.49500(16) 0.37351(16) 0.58728(8) 0.0221(3) Uani 1 1 d . . . . .
H5 H 0.571433 0.316395 0.578677 0.027 Uiso 1 1 calc R U . . .
C6 C 0.45627(19) 0.39687(19) 0.64898(8) 0.0261(3) Uani 1 1 d . . . . .
H6 H 0.505546 0.356562 0.682857 0.031 Uiso 1 1 calc R U . . .
C7 C 0.34367(18) 0.48057(18) 0.66078(7) 0.0251(3) Uani 1 1 d . . . . .
H7 H 0.315527 0.496273 0.703091 0.030 Uiso 1 1 calc R U . . .
C8 C 0.27206(18) 0.54129(16) 0.61171(7) 0.0206(3) Uani 1 1 d . . . . .
H8 H 0.195862 0.598224 0.620977 0.025 Uiso 1 1 calc R U . . .
C9 C 0.31042(14) 0.51996(15) 0.54833(7) 0.0162(3) Uani 1 1 d . . . . .
C10 C 0.16141(16) 0.69317(15) 0.50786(8) 0.0193(3) Uani 1 1 d . . . . .
C11 C 0.06381(18) 0.72448(16) 0.45458(8) 0.0222(3) Uani 1 1 d . . . . .
H11A H -0.028332 0.743989 0.472188 0.027 Uiso 1 1 calc R U . . .
H11B H 0.095839 0.806856 0.432165 0.027 Uiso 1 1 calc R U . . .
C12 C -0.06869(15) 0.52265(17) 0.42462(8) 0.0236(3) Uani 1 1 d . . . . .
H12A H -0.073156 0.447296 0.393734 0.028 Uiso 1 1 calc R U . . .
H12B H -0.153321 0.577433 0.419669 0.028 Uiso 1 1 calc R U . . .
C13 C -0.06687(18) 0.46279(18) 0.49066(9) 0.0271(4) Uani 1 1 d . . . . .
H13A H -0.149826 0.408116 0.497173 0.041 Uiso 1 1 calc R U . . .
H13B H -0.064177 0.536399 0.521781 0.041 Uiso 1 1 calc R U . . .
H13C H 0.014563 0.405218 0.495650 0.041 Uiso 1 1 calc R U . . .
C14 C 0.0255(2) 0.67002(19) 0.34444(9) 0.0291(4) Uani 1 1 d . . . . .
H14A H -0.000884 0.595445 0.315514 0.035 Uiso 1 1 calc R U . . .
H14B H -0.053946 0.732504 0.347657 0.035 Uiso 1 1 calc R U . . .
C15 C 0.1443(3) 0.7462(2) 0.31571(10) 0.0415(5) Uani 1 1 d . . . . .
H15A H 0.116173 0.784922 0.275102 0.062 Uiso 1 1 calc R U . . .
H15B H 0.221470 0.683780 0.309136 0.062 Uiso 1 1 calc R U . . .
H15C H 0.172674 0.819450 0.344210 0.062 Uiso 1 1 calc R U . . .
C16 C 0.53766(14) 0.50714(17) 0.33326(7) 0.0185(2) Uani 1 1 d . . . . .
H16A H 0.600409 0.558017 0.361442 0.022 Uiso 1 1 calc R U . . .
H16B H 0.458792 0.566933 0.323299 0.022 Uiso 1 1 calc R U . . .
C17 C 0.61389(18) 0.47217(17) 0.27177(8) 0.0239(3) Uani 1 1 d . . . . .
H17 H 0.686316 0.409055 0.287930 0.029 Uiso 1 1 calc R U . A 1
C18 C 0.6999(3) 0.5884(3) 0.24947(11) 0.0504(6) Uani 1 1 d . . . . .
H18A H 0.740688 0.565770 0.208498 0.076 Uiso 1 1 calc R U . . .
H18B H 0.773077 0.606054 0.280159 0.076 Uiso 1 1 calc R U . . .
H18C H 0.642291 0.669496 0.245113 0.076 Uiso 1 1 calc R U . . .
C19A C 0.5460(7) 0.3878(8) 0.2281(3) 0.0348(7) Uani 0.348(5) 1 d . . P B 1
H19A H 0.453400 0.423135 0.220228 0.052 Uiso 0.348(5) 1 calc R U P B 1
H19B H 0.539528 0.295506 0.245215 0.052 Uiso 0.348(5) 1 calc R U P B 1
H19C H 0.597720 0.385923 0.188407 0.052 Uiso 0.348(5) 1 calc R U P B 1
C19B C 0.5033(4) 0.4516(4) 0.21720(15) 0.0348(7) Uani 0.652(5) 1 d . . P B 2
H19D H 0.458715 0.538598 0.207929 0.052 Uiso 0.652(5) 1 calc R U P B 2
H19E H 0.433968 0.385716 0.230971 0.052 Uiso 0.652(5) 1 calc R U P B 2
H19F H 0.549093 0.417752 0.179120 0.052 Uiso 0.652(5) 1 calc R U P B 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 N2 1.8859(12) . ?
Ni1 N1 1.8887(12) . ?
Ni1 N3 1.9569(13) . ?
Ni1 Cl1 2.1952(4) . ?
O1 C3 1.3509(18) . ?
O1 C2 1.452(2) . ?
O2 C10 1.2275(19) . ?
N1 C3 1.2900(19) . ?
N1 C1 1.4890(18) . ?
N2 C10 1.3669(19) . ?
N2 C9 1.4078(18) . ?
N3 C11 1.486(2) . ?
N3 C12 1.504(2) . ?
N3 C14 1.510(2) . ?
C1 C16 1.524(2) . ?
C1 C2 1.533(2) . ?
C1 H1 1.0000 . ?
C2 H2A 0.9900 . ?
C2 H2AB 0.9900 . ?
C3 C4 1.447(2) . ?
C4 C5 1.404(2) . ?
C4 C9 1.408(2) . ?
C5 C6 1.380(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.394(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.387(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.409(2) . ?
C8 H8 0.9500 . ?
C10 C11 1.507(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.518(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.507(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.538(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C19A 1.409(6) . ?
C17 C18 1.494(3) . ?
C17 C19B 1.593(4) . ?
C17 H17 1.0000 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19A H19A 0.9800 . ?
C19A H19B 0.9800 . ?
C19A H19C 0.9800 . ?
C19B H19D 0.9800 . ?
C19B H19E 0.9800 . ?
C19B H19F 0.9800 . ?

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
N2 Ni1 N1 92.04(5) . . ?
N2 Ni1 N3 85.95(5) . . ?
N1 Ni1 N3 173.47(6) . . ?
N2 Ni1 Cl1 169.78(4) . . ?
N1 Ni1 Cl1 91.43(4) . . ?
N3 Ni1 Cl1 91.60(4) . . ?
C3 O1 C2 106.28(12) . . ?
C3 N1 C1 108.02(12) . . ?
C3 N1 Ni1 126.06(10) . . ?
C1 N1 Ni1 125.55(10) . . ?
C10 N2 C9 119.49(13) . . ?
C10 N2 Ni1 114.88(10) . . ?
C9 N2 Ni1 125.46(9) . . ?
C11 N3 C12 110.19(13) . . ?
C11 N3 C14 107.97(13) . . ?
C12 N3 C14 106.47(13) . . ?
C11 N3 Ni1 107.07(10) . . ?
C12 N3 Ni1 109.88(9) . . ?
C14 N3 Ni1 115.23(11) . . ?
N1 C1 C16 110.56(12) . . ?
N1 C1 C2 101.68(12) . . ?
C16 C1 C2 113.31(13) . . ?
N1 C1 H1 110.3 . . ?
C16 C1 H1 110.3 . . ?
C2 C1 H1 110.3 . . ?
O1 C2 C1 104.18(12) . . ?
O1 C2 H2A 110.9 . . ?
C1 C2 H2A 110.9 . . ?
O1 C2 H2AB 110.9 . . ?
C1 C2 H2AB 110.9 . . ?
H2A C2 H2AB 108.9 . . ?
N1 C3 O1 116.06(13) . . ?
N1 C3 C4 127.12(13) . . ?
O1 C3 C4 116.80(13) . . ?
C5 C4 C9 120.92(14) . . ?
C5 C4 C3 118.26(14) . . ?
C9 C4 C3 120.82(13) . . ?
C6 C5 C4 120.76(15) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 118.90(15) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C8 C7 C6 121.03(15) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 121.11(15) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C4 C9 N2 120.72(13) . . ?
C4 C9 C8 117.26(13) . . ?
N2 C9 C8 121.98(13) . . ?
O2 C10 N2 127.84(16) . . ?
O2 C10 C11 119.00(14) . . ?
N2 C10 C11 113.15(13) . . ?
N3 C11 C10 112.21(12) . . ?
N3 C11 H11A 109.2 . . ?
C10 C11 H11A 109.2 . . ?
N3 C11 H11B 109.2 . . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
N3 C12 C13 114.72(13) . . ?
N3 C12 H12A 108.6 . . ?
C13 C12 H12A 108.6 . . ?
N3 C12 H12B 108.6 . . ?
C13 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 N3 114.95(17) . . ?
C15 C14 H14A 108.5 . . ?
N3 C14 H14A 108.5 . . ?
C15 C14 H14B 108.5 . . ?
N3 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 C16 C17 112.70(13) . . ?
C1 C16 H16A 109.1 . . ?
C17 C16 H16A 109.1 . . ?
C1 C16 H16B 109.1 . . ?
C17 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
C19A C17 C18 120.4(3) . . ?
C19A C17 C16 117.5(3) . . ?
C18 C17 C16 111.52(16) . . ?
C18 C17 C19B 104.3(2) . . ?
C16 C17 C19B 108.50(17) . . ?
C19A C17 H17 100.9 . . ?
C18 C17 H17 100.9 . . ?
C16 C17 H17 100.9 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19A H19A 109.5 . . ?
C17 C19A H19B 109.5 . . ?
H19A C19A H19B 109.5 . . ?
C17 C19A H19C 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
C17 C19B H19D 109.5 . . ?
C17 C19B H19E 109.5 . . ?
H19D C19B H19E 109.5 . . ?
C17 C19B H19F 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 109.5 . . ?

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
N2 Ni1 N1 C3 15.65(13) . . . . ?
Cl1 Ni1 N1 C3 -154.74(12) . . . . ?
N2 Ni1 N1 C1 -156.46(12) . . . . ?
Cl1 Ni1 N1 C1 33.15(11) . . . . ?
N1 Ni1 N2 C10 154.58(11) . . . . ?
N3 Ni1 N2 C10 -19.20(11) . . . . ?
Cl1 Ni1 N2 C10 -95.6(2) . . . . ?
N1 Ni1 N2 C9 -30.14(12) . . . . ?
N3 Ni1 N2 C9 156.08(12) . . . . ?
Cl1 Ni1 N2 C9 79.7(3) . . . . ?
C3 N1 C1 C16 -105.69(14) . . . . ?
Ni1 N1 C1 C16 67.62(15) . . . . ?
C3 N1 C1 C2 14.91(15) . . . . ?
Ni1 N1 C1 C2 -171.78(10) . . . . ?
C3 O1 C2 C1 16.96(16) . . . . ?
N1 C1 C2 O1 -18.91(15) . . . . ?
C16 C1 C2 O1 99.74(14) . . . . ?
C1 N1 C3 O1 -4.94(18) . . . . ?
Ni1 N1 C3 O1 -178.21(10) . . . . ?
C1 N1 C3 C4 176.66(14) . . . . ?
Ni1 N1 C3 C4 3.4(2) . . . . ?
C2 O1 C3 N1 -8.20(18) . . . . ?
C2 O1 C3 C4 170.37(13) . . . . ?
N1 C3 C4 C5 163.55(15) . . . . ?
O1 C3 C4 C5 -14.8(2) . . . . ?
N1 C3 C4 C9 -15.8(2) . . . . ?
O1 C3 C4 C9 165.85(13) . . . . ?
C9 C4 C5 C6 1.0(2) . . . . ?
C3 C4 C5 C6 -178.31(15) . . . . ?
C4 C5 C6 C7 0.2(3) . . . . ?
C5 C6 C7 C8 -0.8(3) . . . . ?
C6 C7 C8 C9 0.3(2) . . . . ?
C5 C4 C9 N2 -179.29(14) . . . . ?
C3 C4 C9 N2 0.0(2) . . . . ?
C5 C4 C9 C8 -1.5(2) . . . . ?
C3 C4 C9 C8 177.78(14) . . . . ?
C10 N2 C9 C4 -158.53(14) . . . . ?
Ni1 N2 C9 C4 26.39(19) . . . . ?
C10 N2 C9 C8 23.8(2) . . . . ?
Ni1 N2 C9 C8 -151.27(12) . . . . ?
C7 C8 C9 C4 0.9(2) . . . . ?
C7 C8 C9 N2 178.65(14) . . . . ?
C9 N2 C10 O2 15.0(2) . . . . ?
Ni1 N2 C10 O2 -169.37(14) . . . . ?
C9 N2 C10 C11 -166.37(13) . . . . ?
Ni1 N2 C10 C11 9.21(17) . . . . ?
C12 N3 C11 C10 95.44(15) . . . . ?
C14 N3 C11 C10 -148.66(15) . . . . ?
Ni1 N3 C11 C10 -24.03(16) . . . . ?
O2 C10 C11 N3 -170.56(15) . . . . ?
N2 C10 C11 N3 10.7(2) . . . . ?
C11 N3 C12 C13 -57.94(17) . . . . ?
C14 N3 C12 C13 -174.78(14) . . . . ?
Ni1 N3 C12 C13 59.80(15) . . . . ?
C11 N3 C14 C15 69.87(19) . . . . ?
C12 N3 C14 C15 -171.83(15) . . . . ?
Ni1 N3 C14 C15 -49.73(19) . . . . ?
N1 C1 C16 C17 -172.40(13) . . . . ?
C2 C1 C16 C17 74.21(16) . . . . ?
C1 C16 C17 C19A 52.5(4) . . . . ?
C1 C16 C17 C18 -162.43(17) . . . . ?
C1 C16 C17 C19B 83.3(2) . . . . ?

_refine_diff_density_max         0.305
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.042

