# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 1953742'
loop_
_audit_author_name
_audit_author_address
'Jiyan Pei'
;Zhejiang University
China
;
_audit_update_record             
;
2019-11-17 deposited with the CCDC.	2020-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H12 N Ni O4'
_chemical_formula_weight         328.97

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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           123
_space_group_name_H-M_alt        'P 4/m m m'
_space_group_name_Hall           '-P 4 2'

_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, -y, z'
'-y, x, z'
'y, -x, z'
'-x, y, -z'
'x, -y, -z'
'y, x, -z'
'-y, -x, -z'
'-x, -y, -z'
'x, y, -z'
'y, -x, -z'
'-y, x, -z'
'x, -y, z'
'-x, y, z'
'-y, -x, z'
'y, x, z'

_cell_length_a                   10.8865(8)
_cell_length_b                   10.8865(8)
_cell_length_c                   9.3470(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1107.78(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2348
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      25.85

_exptl_crystal_description       Bloc
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.986
_exptl_crystal_F_000             338
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.28
_exptl_absorpt_coefficient_mu    0.885
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.696
_exptl_absorpt_correction_T_max  0.781
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7901
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_av_R_equivalents  0.1057
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.871
_diffrn_reflns_theta_max         25.851
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             663
_reflns_number_gt                560
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_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)+(0.1839P)²+1.7794P] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.029(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         663
_refine_ls_number_parameters     61
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0792
_refine_ls_wR_factor_ref         0.2599
_refine_ls_wR_factor_gt          0.2359
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.111
_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 0.000000 0.000000 0.14210(17) 0.0232(8) Uani 1 8 d S T P . .
N1 N 0.000000 0.000000 0.3624(13) 0.031(3) Uani 1 8 d S T P . .
O1 O -0.019(2) 0.1804(6) 0.1188(7) 0.038(5) Uani 0.5 1 d . . P . .
C1 C 0.000000 0.2345(10) 0.000000 0.048(3) Uani 1 4 d S T P . .
C2 C 0.000000 0.3720(11) 0.000000 0.077(5) Uani 1 4 d S T P . .
C3 C 0.089(2) 0.4332(14) 0.087(2) 0.100(8) Uani 0.375 1 d D U P . .
C4 C 0.182(3) 0.3734(19) 0.162(3) 0.106(8) Uani 0.25 1 d D U P . .
H4A H 0.192754 0.289357 0.149909 0.127 Uiso 0.25 1 calc R U P . .
C5 C 0.258(3) 0.437(2) 0.255(3) 0.109(8) Uani 0.25 1 d D U P . .
H5A H 0.308713 0.393917 0.316970 0.131 Uiso 0.25 1 calc R U P . .
C6 C 0.0492(18) 0.1129(18) 0.4160(17) 0.102(18) Uani 0.5 1 d . . P . .
H6A H 0.069871 0.162879 0.333570 0.122 Uiso 0.5 1 calc R U P A -1
H6C H 0.069869 0.162875 0.498504 0.122 Uiso 0.5 1 calc R U P A -1


_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 1.988(7) . ?
Ni1 O1 1.988(7) 3 ?
Ni1 O1 1.988(7) 13 ?
Ni1 O1 1.988(7) 15 ?
Ni1 O1 1.988(7) 14 ?
Ni1 O1 1.988(7) 4 ?
Ni1 O1 1.988(7) 2 ?
Ni1 O1 1.988(7) 16 ?
Ni1 N1 2.059(12) . ?
Ni1 Ni1 2.656(3) 9 ?
N1 C6 1.43(2) 16 ?
N1 C6 1.43(2) 15 ?
N1 C6 1.43(2) 14 ?
N1 C6 1.43(2) 2 ?
N1 C6 1.43(2) 4 ?
N1 C6 1.43(2) 3 ?
N1 C6 1.43(2) 13 ?
N1 C6 1.43(2) . ?
O1 O1 0.42(5) 14 ?
O1 C1 1.275(9) . ?
C1 C2 1.497(16) . ?
C2 C3 1.43(2) . ?
C2 C3 1.43(2) 5 ?
C2 C3 1.43(2) 10 ?
C2 C3 1.43(2) 14 ?
C3 C4 1.394(10) . ?
C3 C3 1.45(3) 13_565 ?
C3 C3 1.62(4) 10 ?
C3 C3 1.94(5) 14 ?
C4 C5 1.380(10) . ?
C5 C5 1.38(5) 13_565 ?
C6 C6 0.98(4) 16 ?
C6 C6 1.07(4) 14 ?
C6 C6 1.57(3) 10_556 ?
C6 C6 1.85(3) 7_556 ?
C6 C6 1.90(3) 3 ?
C6 C6 1.90(3) 4 ?
C6 C6 1.90(4) 5_556 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Ni1 O1 89.31(4) . 3 ?
O1 Ni1 O1 162.4(10) . 13 ?
O1 Ni1 O1 77.1(14) 3 13 ?
O1 Ni1 O1 77.1(14) . 15 ?
O1 Ni1 O1 12.2(14) 3 15 ?
O1 Ni1 O1 89.31(4) 13 15 ?
O1 Ni1 O1 12.2(14) . 14 ?
O1 Ni1 O1 101.5(14) 3 14 ?
O1 Ni1 O1 167.4(4) 13 14 ?
O1 Ni1 O1 89.31(4) 15 14 ?
O1 Ni1 O1 89.32(4) . 4 ?
O1 Ni1 O1 167.4(4) 3 4 ?
O1 Ni1 O1 101.5(14) 13 4 ?
O1 Ni1 O1 162.4(10) 15 4 ?
O1 Ni1 O1 77.1(14) 14 4 ?
O1 Ni1 O1 167.4(4) . 2 ?
O1 Ni1 O1 89.31(4) 3 2 ?
O1 Ni1 O1 12.2(14) 13 2 ?
O1 Ni1 O1 101.5(14) 15 2 ?
O1 Ni1 O1 162.4(10) 14 2 ?
O1 Ni1 O1 89.31(4) 4 2 ?
O1 Ni1 O1 101.5(14) . 16 ?
O1 Ni1 O1 162.4(10) 3 16 ?
O1 Ni1 O1 89.31(4) 13 16 ?
O1 Ni1 O1 167.4(4) 15 16 ?
O1 Ni1 O1 89.31(4) 14 16 ?
O1 Ni1 O1 12.2(14) 4 16 ?
O1 Ni1 O1 77.1(14) 2 16 ?
O1 Ni1 N1 96.3(2) . . ?
O1 Ni1 N1 96.3(2) 3 . ?
O1 Ni1 N1 96.3(2) 13 . ?
O1 Ni1 N1 96.3(2) 15 . ?
O1 Ni1 N1 96.3(2) 14 . ?
O1 Ni1 N1 96.3(2) 4 . ?
O1 Ni1 N1 96.3(2) 2 . ?
O1 Ni1 N1 96.3(2) 16 . ?
O1 Ni1 Ni1 83.7(2) . 9 ?
O1 Ni1 Ni1 83.7(2) 3 9 ?
O1 Ni1 Ni1 83.7(2) 13 9 ?
O1 Ni1 Ni1 83.7(2) 15 9 ?
O1 Ni1 Ni1 83.7(2) 14 9 ?
O1 Ni1 Ni1 83.7(2) 4 9 ?
O1 Ni1 Ni1 83.7(2) 2 9 ?
O1 Ni1 Ni1 83.7(2) 16 9 ?
N1 Ni1 Ni1 180.0 . 9 ?
C6 N1 C6 139.0(16) 16 15 ?
C6 N1 C6 82.9(5) 16 14 ?
C6 N1 C6 82.9(5) 15 14 ?
C6 N1 C6 121.3(16) 16 2 ?
C6 N1 C6 40.1(16) 15 2 ?
C6 N1 C6 118.3(15) 14 2 ?
C6 N1 C6 43.9(16) 16 4 ?
C6 N1 C6 118.3(15) 15 4 ?
C6 N1 C6 121.3(16) 14 4 ?
C6 N1 C6 82.9(5) 2 4 ?
C6 N1 C6 118.3(15) 16 3 ?
C6 N1 C6 43.9(16) 15 3 ?
C6 N1 C6 40.1(16) 14 3 ?
C6 N1 C6 82.9(5) 2 3 ?
C6 N1 C6 139.0(16) 4 3 ?
C6 N1 C6 82.9(5) 16 13 ?
C6 N1 C6 82.9(5) 15 13 ?
C6 N1 C6 139.0(16) 14 13 ?
C6 N1 C6 43.9(16) 2 13 ?
C6 N1 C6 40.1(16) 4 13 ?
C6 N1 C6 121.3(16) 3 13 ?
C6 N1 C6 40.1(15) 16 . ?
C6 N1 C6 121.3(16) 15 . ?
C6 N1 C6 43.9(16) 14 . ?
C6 N1 C6 139.0(16) 2 . ?
C6 N1 C6 82.9(5) 4 . ?
C6 N1 C6 82.9(5) 3 . ?
C6 N1 C6 118.3(15) 13 . ?
C6 N1 Ni1 110.5(8) 16 . ?
C6 N1 Ni1 110.5(8) 15 . ?
C6 N1 Ni1 110.5(8) 14 . ?
C6 N1 Ni1 110.5(8) 2 . ?
C6 N1 Ni1 110.5(8) 4 . ?
C6 N1 Ni1 110.5(8) 3 . ?
C6 N1 Ni1 110.5(8) 13 . ?
C6 N1 Ni1 110.5(8) . . ?
O1 O1 C1 80.4(11) 14 . ?
O1 O1 Ni1 83.9(7) 14 . ?
C1 O1 Ni1 122.3(7) . . ?
O1 C1 O1 121.2(12) . 10 ?
O1 C1 O1 125.0(10) . 5 ?
O1 C1 O1 19(2) 10 5 ?
O1 C1 O1 19(2) . 14 ?
O1 C1 O1 125.0(10) 10 14 ?
O1 C1 O1 121.2(12) 5 14 ?
O1 C1 C2 117.5(5) . . ?
O1 C1 C2 117.5(5) 10 . ?
O1 C1 C2 117.5(5) 5 . ?
O1 C1 C2 117.5(5) 14 . ?
C3 C2 C3 124.3(16) . 5 ?
C3 C2 C3 69(2) . 10 ?
C3 C2 C3 85(2) 5 10 ?
C3 C2 C3 85(2) . 14 ?
C3 C2 C3 69(2) 5 14 ?
C3 C2 C3 124.3(16) 10 14 ?
C3 C2 C1 117.9(8) . . ?
C3 C2 C1 117.9(8) 5 . ?
C3 C2 C1 117.9(8) 10 . ?
C3 C2 C1 117.9(8) 14 . ?
C4 C3 C2 124.1(15) . . ?
C4 C3 C3 117.8(11) . 13_565 ?
C2 C3 C3 117.9(8) . 13_565 ?
C4 C3 C3 120.4(17) . 10 ?
C2 C3 C3 55.5(10) . 10 ?
C3 C3 C3 89.999(3) 13_565 10 ?
C4 C3 C3 136.4(17) . 14 ?
C2 C3 C3 47.3(11) . 14 ?
C3 C3 C3 89.998(3) 13_565 14 ?
C3 C3 C3 89.999(2) 10 14 ?
C5 C4 C3 121.2(17) . . ?
C5 C5 C4 119.9(12) 13_565 . ?
C6 C6 C6 134.998(3) 16 14 ?
C6 C6 N1 70.0(8) 16 . ?
C6 C6 N1 68.0(8) 14 . ?
C6 C6 C6 90.000(1) 16 10_556 ?
C6 C6 C6 90.001(2) 14 10_556 ?
N1 C6 C6 110.5(8) . 10_556 ?
C6 C6 C6 58.0(12) 16 7_556 ?
C6 C6 C6 112.0(8) 14 7_556 ?
N1 C6 C6 96.6(11) . 7_556 ?
C6 C6 C6 32.0(12) 10_556 7_556 ?
C6 C6 C6 113.5(8) 16 3 ?
C6 C6 C6 21.5(8) 14 3 ?
N1 C6 C6 48.5(3) . 3 ?
C6 C6 C6 90.001(4) 10_556 3 ?
C6 C6 C6 102.2(2) 7_556 3 ?
C6 C6 C6 23.5(8) 16 4 ?
C6 C6 C6 111.5(8) 14 4 ?
N1 C6 C6 48.5(3) . 4 ?
C6 C6 C6 89.999(1) 10_556 4 ?
C6 C6 C6 60.9(12) 7_556 4 ?
C6 C6 C6 89.999(2) 3 4 ?
C6 C6 C6 113.5(7) 16 5_556 ?
C6 C6 C6 55.7(11) 14 5_556 ?
N1 C6 C6 94.5(11) . 5_556 ?
C6 C6 C6 34.3(11) 10_556 5_556 ?
C6 C6 C6 60.7(12) 7_556 5_556 ?
C6 C6 C6 58.4(12) 3 5_556 ?
C6 C6 C6 101.9(3) 4 5_556 ?

_refine_diff_density_max         0.958
_refine_diff_density_min         -0.715
_refine_diff_density_rms         0.175

