# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_SPA629_sq
_database_code_depnum_ccdc_archive 'CCDC 2246022'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2023-03-03 deposited with the CCDC.	2023-05-10 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         'C14 H18 N2 Ni O5'
_chemical_formula_sum            'C14 H18 N2 Ni O5'
_chemical_formula_weight         353.01

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0021 0.0012 '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 0.0044 0.0025 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0080 0.0047 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3389 0.8999 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_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'

_cell_length_a                   6.0610(12)
_cell_length_b                   7.0090(14)
_cell_length_c                   10.677(2)
_cell_angle_alpha                89.49(3)
_cell_angle_beta                 84.51(3)
_cell_angle_gamma                87.40(3)
_cell_volume                     451.03(16)
_cell_formula_units_Z            1
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    28374
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      33.548

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_F_000             184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.074
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_min          0.015
_exptl_absorpt_coefficient_mu    0.788
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.822
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.630
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16737
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.698
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        22.210
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4575
_reflns_number_gt                4485
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.999
_reflns_Friedel_fraction_max     0.999
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'PAL BL2D-SMDC Program(Shin et.al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2018(Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 4(Putx&Brandenburg, 2014)'
_computing_publication_material  'publCIF(Westrip, 2010)'
_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)+(0.1559P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2173 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.043(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4575
_refine_ls_number_parameters     205
_refine_ls_number_restraints     135
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0760
_refine_ls_wR_factor_ref         0.1861
_refine_ls_wR_factor_gt          0.1852
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.112
_refine_ls_shift/su_max          0.000
_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 0.41840(2) 0.42061(2) 0.88375(2) 0.0117(2) Uani 1 1 d . . . . .
O1 O 0.5245(12) 0.4210(11) 0.7024(6) 0.0209(13) Uani 1 1 d . . . . .
O2 O 0.8918(12) 0.3819(17) 0.6537(6) 0.059(3) Uani 1 1 d . . . . .
O3 O 0.3436(11) 0.4208(9) 0.0753(6) 0.0165(13) Uani 1 1 d . . . . .
O4 O 0.6988(9) 0.4072(7) 0.0101(5) 0.0185(9) Uani 1 1 d . . . . .
O5 O 0.0888(8) 0.4389(7) 0.8569(5) 0.0184(9) Uani 1 1 d D . . . .
H1O5 H 0.010(12) 0.551(6) 0.843(11) 0.028 Uiso 1 1 d D U . . .
H2O5 H 0.006(12) 0.335(7) 0.845(10) 0.028 Uiso 1 1 d D U . . .
N1 N 0.4194(11) 0.7335(10) 0.8796(6) 0.0103(10) Uani 1 1 d . U . . .
N2 N 0.4180(11) 1.1095(10) 0.8796(6) 0.0103(10) Uani 1 1 d . U . . .
C1 C 0.6989(12) 0.4029(11) 0.6265(7) 0.0213(13) Uani 1 1 d . . . . .
C2 C 0.6598(11) 0.4048(10) 0.4885(7) 0.0183(12) Uani 1 1 d . . . . .
C3 C 0.4460(17) 0.4215(19) 0.4529(10) 0.034(3) Uani 1 1 d . . . . .
H3 H 0.324264 0.431759 0.514367 0.041 Uiso 1 1 calc R U . . .
C4 C 0.4117(16) 0.423(2) 0.3258(9) 0.035(3) Uani 1 1 d . . . . .
H4 H 0.266359 0.431333 0.301806 0.042 Uiso 1 1 calc R U . . .
C5 C 0.5923(11) 0.4120(10) 0.2334(6) 0.0159(11) Uani 1 1 d . . . . .
C6 C 0.8060(12) 0.3912(14) 0.2682(7) 0.0264(15) Uani 1 1 d . . . . .
H6 H 0.927293 0.379866 0.206484 0.032 Uiso 1 1 calc R U . . .
C7 C 0.8407(12) 0.3871(14) 0.3963(7) 0.0279(16) Uani 1 1 d . . . . .
H7 H 0.985633 0.372481 0.420400 0.033 Uiso 1 1 calc R U . . .
C8 C 0.5439(12) 0.4128(9) 0.0983(6) 0.0152(11) Uani 1 1 d . . . . .
C9 C 0.3160(14) 0.8169(10) 0.7695(7) 0.0237(14) Uani 1 1 d . . . . .
H9A H 0.160967 0.781232 0.773470 0.028 Uiso 1 1 calc R U . . .
H9B H 0.393638 0.764138 0.691921 0.028 Uiso 1 1 calc R U . . .
C10 C 0.3248(15) 1.0351(10) 0.7662(7) 0.0256(15) Uani 1 1 d . . . . .
H10A H 0.416691 1.073761 0.690503 0.031 Uiso 1 1 calc R U . . .
H10B H 0.174810 1.091301 0.761554 0.031 Uiso 1 1 calc R U . . .
C11 C 0.2918(14) 0.8145(10) 0.9928(7) 0.0238(14) Uani 1 1 d . . . . .
H11A H 0.360440 0.769312 1.067698 0.029 Uiso 1 1 calc R U . . .
H11B H 0.140475 0.769405 0.998433 0.029 Uiso 1 1 calc R U . . .
C12 C 0.2829(14) 1.0336(10) 0.9900(7) 0.0253(15) Uani 1 1 d . . . . .
H12A H 0.128525 1.080648 0.988037 0.030 Uiso 1 1 calc R U . . .
H12B H 0.336963 1.080842 1.067018 0.030 Uiso 1 1 calc R U . . .
C13 C 0.6475(11) 0.8032(10) 0.8739(8) 0.0231(14) Uani 1 1 d . . . . .
H13A H 0.731433 0.759660 0.795518 0.028 Uiso 1 1 calc R U . . .
H13B H 0.722246 0.748785 0.944282 0.028 Uiso 1 1 calc R U . . .
C14 C 0.6462(12) 1.0216(10) 0.8797(8) 0.0241(14) Uani 1 1 d . . . . .
H14A H 0.709862 1.059558 0.956244 0.029 Uiso 1 1 calc R U . . .
H14B H 0.739382 1.069678 0.807268 0.029 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 O1 1.981(7) . ?
Ni1 O5 2.043(5) . ?
Ni1 O3 2.052(6) 1_556 ?
Ni1 N2 2.181(7) 1_545 ?
Ni1 N1 2.194(7) . ?
Ni1 O4 2.267(5) 1_556 ?
Ni1 C8 2.481(7) 1_556 ?
O1 C1 1.272(10) . ?
O2 C1 1.233(10) . ?
O3 C8 1.260(10) . ?
O4 C8 1.264(8) . ?
O5 H1O5 0.922(15) . ?
O5 H2O5 0.920(15) . ?
N1 C11 1.474(10) . ?
N1 C13 1.483(9) . ?
N1 C9 1.487(10) . ?
N2 C12 1.478(10) . ?
N2 C14 1.488(10) . ?
N2 C10 1.493(10) . ?
C1 C2 1.515(9) . ?
C2 C3 1.385(12) . ?
C2 C7 1.403(9) . ?
C3 C4 1.392(9) . ?
C3 H3 0.9400 . ?
C4 C5 1.402(12) . ?
C4 H4 0.9400 . ?
C5 C6 1.383(9) . ?
C5 C8 1.499(9) . ?
C6 C7 1.403(9) . ?
C6 H6 0.9400 . ?
C7 H7 0.9400 . ?
C9 C10 1.532(10) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C11 C12 1.534(10) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C13 C14 1.533(10) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 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
O1 Ni1 O5 95.3(3) . . ?
O1 Ni1 O3 173.9(3) . 1_556 ?
O5 Ni1 O3 90.8(2) . 1_556 ?
O1 Ni1 N2 89.3(3) . 1_545 ?
O5 Ni1 N2 90.7(2) . 1_545 ?
O3 Ni1 N2 91.1(3) 1_556 1_545 ?
O1 Ni1 N1 88.4(3) . . ?
O5 Ni1 N1 88.9(2) . . ?
O3 Ni1 N1 91.2(3) 1_556 . ?
N2 Ni1 N1 177.7(3) 1_545 . ?
O1 Ni1 O4 113.0(3) . 1_556 ?
O5 Ni1 O4 151.7(2) . 1_556 ?
O3 Ni1 O4 60.9(2) 1_556 1_556 ?
N2 Ni1 O4 90.7(2) 1_545 1_556 ?
N1 Ni1 O4 90.8(2) . 1_556 ?
O1 Ni1 C8 143.4(3) . 1_556 ?
O5 Ni1 C8 121.2(2) . 1_556 ?
O3 Ni1 C8 30.4(3) 1_556 1_556 ?
N2 Ni1 C8 91.1(2) 1_545 1_556 ?
N1 Ni1 C8 91.0(2) . 1_556 ?
O4 Ni1 C8 30.4(2) 1_556 1_556 ?
C1 O1 Ni1 142.6(6) . . ?
C8 O3 Ni1 93.9(5) . 1_554 ?
C8 O4 Ni1 84.2(4) . 1_554 ?
Ni1 O5 H1O5 124(5) . . ?
Ni1 O5 H2O5 124(5) . . ?
H1O5 O5 H2O5 111(2) . . ?
C11 N1 C13 108.1(6) . . ?
C11 N1 C9 106.6(7) . . ?
C13 N1 C9 107.0(6) . . ?
C11 N1 Ni1 110.6(5) . . ?
C13 N1 Ni1 111.9(5) . . ?
C9 N1 Ni1 112.5(5) . . ?
C12 N2 C14 107.6(7) . . ?
C12 N2 C10 106.4(7) . . ?
C14 N2 C10 106.5(7) . . ?
C12 N2 Ni1 111.3(5) . 1_565 ?
C14 N2 Ni1 111.6(5) . 1_565 ?
C10 N2 Ni1 113.1(5) . 1_565 ?
O2 C1 O1 127.0(7) . . ?
O2 C1 C2 117.9(7) . . ?
O1 C1 C2 115.0(7) . . ?
C3 C2 C7 119.8(7) . . ?
C3 C2 C1 120.2(7) . . ?
C7 C2 C1 119.9(6) . . ?
C2 C3 C4 119.8(7) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 120.5(7) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 120.0(7) . . ?
C6 C5 C8 122.1(6) . . ?
C4 C5 C8 117.8(7) . . ?
C5 C6 C7 119.5(6) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C6 C7 C2 120.3(6) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
O3 C8 O4 121.0(6) . . ?
O3 C8 C5 117.8(6) . . ?
O4 C8 C5 121.2(6) . . ?
O3 C8 Ni1 55.6(4) . 1_554 ?
O4 C8 Ni1 65.4(3) . 1_554 ?
C5 C8 Ni1 173.4(5) . 1_554 ?
N1 C9 C10 111.6(6) . . ?
N1 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
N1 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
N2 C10 C9 111.7(6) . . ?
N2 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
N2 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
N1 C11 C12 111.6(6) . . ?
N1 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
N1 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
N2 C12 C11 112.1(6) . . ?
N2 C12 H12A 109.2 . . ?
C11 C12 H12A 109.2 . . ?
N2 C12 H12B 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
N1 C13 C14 111.6(6) . . ?
N1 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
N1 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
N2 C14 C13 111.9(6) . . ?
N2 C14 H14A 109.2 . . ?
C13 C14 H14A 109.2 . . ?
N2 C14 H14B 109.2 . . ?
C13 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?

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 C1 O2 -3.4(17) . . . . ?
Ni1 O1 C1 C2 175.6(7) . . . . ?
O2 C1 C2 C3 177.8(11) . . . . ?
O1 C1 C2 C3 -1.2(12) . . . . ?
O2 C1 C2 C7 -1.4(12) . . . . ?
O1 C1 C2 C7 179.6(8) . . . . ?
C7 C2 C3 C4 -0.8(14) . . . . ?
C1 C2 C3 C4 -179.9(8) . . . . ?
C2 C3 C4 C5 -1.4(14) . . . . ?
C3 C4 C5 C6 2.8(14) . . . . ?
C3 C4 C5 C8 179.6(8) . . . . ?
C4 C5 C6 C7 -2.0(14) . . . . ?
C8 C5 C6 C7 -178.6(7) . . . . ?
C5 C6 C7 C2 -0.3(14) . . . . ?
C3 C2 C7 C6 1.7(14) . . . . ?
C1 C2 C7 C6 -179.2(8) . . . . ?
Ni1 O3 C8 O4 -0.4(7) 1_554 . . . ?
Ni1 O3 C8 C5 179.1(5) 1_554 . . . ?
Ni1 O4 C8 O3 0.3(6) 1_554 . . . ?
Ni1 O4 C8 C5 -179.2(6) 1_554 . . . ?
C6 C5 C8 O3 175.8(7) . . . . ?
C4 C5 C8 O3 -0.9(11) . . . . ?
C6 C5 C8 O4 -4.8(11) . . . . ?
C4 C5 C8 O4 178.6(8) . . . . ?
C11 N1 C9 C10 60.4(8) . . . . ?
C13 N1 C9 C10 -55.0(8) . . . . ?
Ni1 N1 C9 C10 -178.2(5) . . . . ?
C12 N2 C10 C9 -54.6(9) . . . . ?
C14 N2 C10 C9 59.9(9) . . . . ?
Ni1 N2 C10 C9 -177.1(5) 1_565 . . . ?
N1 C9 C10 N2 -4.7(9) . . . . ?
C13 N1 C11 C12 59.3(9) . . . . ?
C9 N1 C11 C12 -55.4(9) . . . . ?
Ni1 N1 C11 C12 -178.0(6) . . . . ?
C14 N2 C12 C11 -54.0(9) . . . . ?
C10 N2 C12 C11 59.8(9) . . . . ?
Ni1 N2 C12 C11 -176.6(6) 1_565 . . . ?
N1 C11 C12 N2 -4.3(10) . . . . ?
C11 N1 C13 C14 -54.3(9) . . . . ?
C9 N1 C13 C14 60.1(8) . . . . ?
Ni1 N1 C13 C14 -176.2(5) . . . . ?
C12 N2 C14 C13 58.9(9) . . . . ?
C10 N2 C14 C13 -54.9(8) . . . . ?
Ni1 N2 C14 C13 -178.7(5) 1_565 . . . ?
N1 C13 C14 N2 -4.4(9) . . . . ?

_refine_diff_density_max         5.150
_refine_diff_density_min         -0.851
_refine_diff_density_rms         0.232























