# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 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_1
_database_code_depnum_ccdc_archive 'CCDC 2089652'
loop_
_audit_author_name
_audit_author_address
'Zixin You'
;Liaoning Normal University
China
;
_audit_update_record             
;
2021-06-13 deposited with the CCDC.	2021-10-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 Cu N2 O12'
_chemical_formula_weight         515.87

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.9839(5)
_cell_length_b                   6.4217(6)
_cell_length_c                   15.1325(14)
_cell_angle_alpha                93.911(2)
_cell_angle_beta                 94.548(2)
_cell_angle_gamma                106.073(2)
_cell_volume                     461.86(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2106
_cell_measurement_theta_min      1.36
_cell_measurement_theta_max      27.85

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            BLUE
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.855
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             263
_exptl_absorpt_coefficient_mu    1.261
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7501
_exptl_absorpt_correction_T_max  0.9838
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            2920
_diffrn_reflns_av_R_equivalents  0.0158
_diffrn_reflns_av_sigmaI/netI    0.0402
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.36
_diffrn_reflns_theta_max         27.85
_reflns_number_total             2106
_reflns_number_gt                1902
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0402P)²+1.2110P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2106
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1189
_refine_ls_wR_factor_gt          0.1088
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 0.5000 0.5000 0.02147(18) Uani 1 2 d S . .
C1 C 0.6777(7) 0.6844(6) 0.3351(2) 0.0246(7) Uani 1 1 d . . .
C2 C 0.9062(8) 0.8314(8) 0.2889(2) 0.0377(10) Uani 1 1 d . . .
H2A H 0.9927 0.9643 0.3273 0.045 Uiso 1 1 calc R . .
H2B H 1.0498 0.7593 0.2789 0.045 Uiso 1 1 calc R . .
C3 C 0.6422(8) 1.0355(6) 0.2067(2) 0.0319(8) Uani 1 1 d . . .
C4 C 0.5213(7) 1.0847(6) 0.1209(2) 0.0291(8) Uani 1 1 d . . .
C5 C 0.3730(8) 1.2371(6) 0.1196(3) 0.0312(8) Uani 1 1 d . . .
H5 H 0.3488 1.3085 0.1727 0.037 Uiso 1 1 calc R . .
C6 C 0.5576(7) 0.9758(6) 0.0412(2) 0.0263(7) Uani 1 1 d . . .
C7 C 0.7412(8) 0.7159(6) -0.0382(3) 0.0323(8) Uani 1 1 d . . .
H7 H 0.8405 0.6128 -0.0379 0.039 Uiso 1 1 calc R . .
C8 C 0.7088(7) 0.8193(6) 0.0407(2) 0.0276(8) Uani 1 1 d . . .
C9 C 0.8326(7) 0.7686(6) 0.1259(3) 0.0317(8) Uani 1 1 d . . .
N5 N 0.7965(6) 0.8862(6) 0.2035(2) 0.0339(8) Uani 1 1 d . . .
O1 O 0.1852(6) 0.3772(7) 0.40999(19) 0.0659(12) Uani 1 1 d . . .
H1A H 0.0833 0.4635 0.4070 0.099 Uiso 1 1 d R . .
H1B H 0.2461 0.3608 0.3599 0.099 Uiso 1 1 d R . .
O2 O 0.6567(7) 0.1832(5) 0.4673(3) 0.0705(12) Uani 1 1 d . . .
H2C H 0.6167 0.1411 0.4121 0.106 Uiso 1 1 d R . .
H2D H 0.8333 0.2152 0.4802 0.106 Uiso 1 1 d R . .
O3 O 0.7520(5) 0.6492(5) 0.41400(16) 0.0347(6) Uani 1 1 d . . .
O4 O 0.4432(6) 0.6074(5) 0.29485(17) 0.0430(7) Uani 1 1 d . . .
O5 O 0.6104(7) 1.1213(5) 0.27793(19) 0.0462(8) Uani 1 1 d . . .
O6 O 0.9610(6) 0.6341(5) 0.12989(19) 0.0451(8) Uani 1 1 d . . .


_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
Cu1 O1 1.941(3) 2_666 ?
Cu1 O1 1.941(3) . ?
Cu1 O3 1.988(2) . ?
Cu1 O3 1.988(2) 2_666 ?
Cu1 O2 2.408(3) . ?
Cu1 O2 2.408(3) 2_666 ?
C1 O4 1.227(4) . ?
C1 O3 1.276(4) . ?
C1 C2 1.515(5) . ?
C2 N5 1.466(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 O5 1.219(5) . ?
C3 N5 1.386(5) . ?
C3 C4 1.478(5) . ?
C4 C5 1.380(5) . ?
C4 C6 1.402(5) . ?
C5 C7 1.402(5) 2_675 ?
C5 H5 0.9300 . ?
C6 C8 1.413(5) . ?
C6 C6 1.422(6) 2_675 ?
C7 C8 1.369(6) . ?
C7 C5 1.402(5) 2_675 ?
C7 H7 0.9300 . ?
C8 C9 1.480(5) . ?
C9 O6 1.211(5) . ?
C9 N5 1.404(5) . ?
O1 H1A 0.8500 . ?
O1 H1B 0.8500 . ?
O2 H2C 0.8500 . ?
O2 H2D 0.8500 . ?

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 Cu1 O1 180.0 2_666 . ?
O1 Cu1 O3 85.98(12) 2_666 . ?
O1 Cu1 O3 94.02(12) . . ?
O1 Cu1 O3 94.02(12) 2_666 2_666 ?
O1 Cu1 O3 85.98(12) . 2_666 ?
O3 Cu1 O3 179.999(1) . 2_666 ?
O1 Cu1 O2 91.82(17) 2_666 . ?
O1 Cu1 O2 88.19(17) . . ?
O3 Cu1 O2 88.10(12) . . ?
O3 Cu1 O2 91.90(12) 2_666 . ?
O1 Cu1 O2 88.18(17) 2_666 2_666 ?
O1 Cu1 O2 91.82(17) . 2_666 ?
O3 Cu1 O2 91.90(12) . 2_666 ?
O3 Cu1 O2 88.10(12) 2_666 2_666 ?
O2 Cu1 O2 180.000(1) . 2_666 ?
O4 C1 O3 125.6(3) . . ?
O4 C1 C2 119.1(3) . . ?
O3 C1 C2 115.3(3) . . ?
N5 C2 C1 112.0(3) . . ?
N5 C2 H2A 109.2 . . ?
C1 C2 H2A 109.2 . . ?
N5 C2 H2B 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
O5 C3 N5 120.4(3) . . ?
O5 C3 C4 122.3(4) . . ?
N5 C3 C4 117.2(3) . . ?
C5 C4 C6 120.4(3) . . ?
C5 C4 C3 119.9(4) . . ?
C6 C4 C3 119.7(3) . . ?
C4 C5 C7 119.9(4) . 2_675 ?
C4 C5 H5 120.0 . . ?
C7 C5 H5 120.0 2_675 . ?
C4 C6 C8 121.5(3) . . ?
C4 C6 C6 119.6(4) . 2_675 ?
C8 C6 C6 118.9(4) . 2_675 ?
C8 C7 C5 121.1(3) . 2_675 ?
C8 C7 H7 119.5 . . ?
C5 C7 H7 119.5 2_675 . ?
C7 C8 C6 120.1(3) . . ?
C7 C8 C9 120.3(3) . . ?
C6 C8 C9 119.6(3) . . ?
O6 C9 N5 120.6(3) . . ?
O6 C9 C8 122.7(4) . . ?
N5 C9 C8 116.7(3) . . ?
C3 N5 C9 125.2(3) . . ?
C3 N5 C2 117.0(3) . . ?
C9 N5 C2 117.5(3) . . ?
Cu1 O1 H1A 109.1 . . ?
Cu1 O1 H1B 109.4 . . ?
H1A O1 H1B 109.5 . . ?
Cu1 O2 H2C 109.2 . . ?
Cu1 O2 H2D 109.4 . . ?
H2C O2 H2D 109.5 . . ?
C1 O3 Cu1 126.4(2) . . ?

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
O4 C1 C2 N5 8.4(5) . . . . ?
O3 C1 C2 N5 -172.7(3) . . . . ?
O5 C3 C4 C5 1.9(6) . . . . ?
N5 C3 C4 C5 -178.0(3) . . . . ?
O5 C3 C4 C6 -178.0(4) . . . . ?
N5 C3 C4 C6 2.1(5) . . . . ?
C6 C4 C5 C7 -0.3(5) . . . 2_675 ?
C3 C4 C5 C7 179.9(3) . . . 2_675 ?
C5 C4 C6 C8 179.9(3) . . . . ?
C3 C4 C6 C8 -0.2(5) . . . . ?
C5 C4 C6 C6 0.5(6) . . . 2_675 ?
C3 C4 C6 C6 -179.7(4) . . . 2_675 ?
C5 C7 C8 C6 0.2(6) 2_675 . . . ?
C5 C7 C8 C9 -179.6(3) 2_675 . . . ?
C4 C6 C8 C7 -179.9(3) . . . . ?
C6 C6 C8 C7 -0.4(6) 2_675 . . . ?
C4 C6 C8 C9 -0.1(5) . . . . ?
C6 C6 C8 C9 179.4(4) 2_675 . . . ?
C7 C8 C9 O6 -1.3(6) . . . . ?
C6 C8 C9 O6 179.0(3) . . . . ?
C7 C8 C9 N5 178.3(3) . . . . ?
C6 C8 C9 N5 -1.5(5) . . . . ?
O5 C3 N5 C9 176.1(4) . . . . ?
C4 C3 N5 C9 -4.1(5) . . . . ?
O5 C3 N5 C2 2.6(6) . . . . ?
C4 C3 N5 C2 -177.6(3) . . . . ?
O6 C9 N5 C3 -176.7(4) . . . . ?
C8 C9 N5 C3 3.8(5) . . . . ?
O6 C9 N5 C2 -3.2(5) . . . . ?
C8 C9 N5 C2 177.2(3) . . . . ?
C1 C2 N5 C3 74.4(5) . . . . ?
C1 C2 N5 C9 -99.6(4) . . . . ?
O4 C1 O3 Cu1 -10.1(5) . . . . ?
C2 C1 O3 Cu1 171.0(3) . . . . ?
O1 Cu1 O3 C1 -164.6(3) 2_666 . . . ?
O1 Cu1 O3 C1 15.4(3) . . . . ?
O3 Cu1 O3 C1 -151(17) 2_666 . . . ?
O2 Cu1 O3 C1 103.4(3) . . . . ?
O2 Cu1 O3 C1 -76.6(3) 2_666 . . . ?

_diffrn_measured_fraction_theta_max 0.958
_diffrn_reflns_theta_full        27.85
_diffrn_measured_fraction_theta_full 0.958
_refine_diff_density_max         0.634
_refine_diff_density_min         -0.649
_refine_diff_density_rms         0.102
####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2089654'
loop_
_audit_author_name
_audit_author_address
'Zixin You'
;Liaoning Normal University
China
;
_audit_update_record             
;
2021-06-13 deposited with the CCDC.	2021-10-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 N2 Ni O12'
_chemical_formula_weight         511.04

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.0205(4)
_cell_length_b                   6.3112(5)
_cell_length_c                   15.0941(13)
_cell_angle_alpha                95.2790(10)
_cell_angle_beta                 95.0440(10)
_cell_angle_gamma                105.1340(10)
_cell_volume                     456.59(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1532
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      31.08

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            olive
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.859
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             262
_exptl_absorpt_coefficient_mu    1.142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5934
_exptl_absorpt_correction_T_max  0.7113
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            2360
_diffrn_reflns_av_R_equivalents  0.0111
_diffrn_reflns_av_sigmaI/netI    0.0221
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.73
_diffrn_reflns_theta_max         24.99
_reflns_number_total             1605
_reflns_number_gt                1507
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0433P)²+0.7520P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1605
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.0921
_refine_ls_wR_factor_gt          0.0908
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.5000 0.5000 0.0000 0.01949(18) Uani 1 2 d S . .
C1 C 0.3128(6) 0.3034(5) 0.16305(18) 0.0239(6) Uani 1 1 d . . .
C2 C 0.0891(6) 0.1525(6) 0.2073(2) 0.0333(7) Uani 1 1 d . . .
H2A H -0.0578 0.2232 0.2165 0.040 Uiso 1 1 calc R . .
H2B H 0.0095 0.0159 0.1679 0.040 Uiso 1 1 calc R . .
C3 C 0.3602(6) -0.0471(5) 0.2911(2) 0.0283(7) Uani 1 1 d . . .
C4 C 0.1636(6) 0.2259(5) 0.3713(2) 0.0293(7) Uani 1 1 d . . .
C5 C 0.4823(6) -0.0928(5) 0.3780(2) 0.0253(6) Uani 1 1 d . . .
C6 C 0.2882(6) 0.1794(5) 0.4580(2) 0.0255(6) Uani 1 1 d . . .
C7 C 0.6341(6) -0.2454(5) 0.3807(2) 0.0294(7) Uani 1 1 d . . .
H7 H 0.6609 -0.3201 0.3276 0.035 Uiso 1 1 calc R . .
C8 C 0.4419(6) 0.0219(5) 0.45860(19) 0.0234(6) Uani 1 1 d . . .
C9 C 0.2516(6) 0.2888(5) 0.5372(2) 0.0297(7) Uani 1 1 d . . .
H9 H 0.1499 0.3926 0.5362 0.036 Uiso 1 1 calc R . .
N1 N 0.1998(5) 0.1018(5) 0.29385(17) 0.0299(6) Uani 1 1 d . . .
O1 O 0.8223(5) 0.6152(6) 0.09708(15) 0.0629(9) Uani 1 1 d . . .
H1B H 0.8119 0.5238 0.1355 0.094 Uiso 1 1 d R . .
H1A H 0.9737 0.6296 0.0741 0.094 Uiso 1 1 d R . .
O2 O 0.6328(6) 0.2108(4) -0.0328(2) 0.0590(8) Uani 1 1 d . . .
H2D H 0.7054 0.1751 0.0146 0.088 Uiso 1 1 d R . .
H2C H 0.4937 0.1056 -0.0559 0.088 Uiso 1 1 d R . .
O3 O 0.2361(4) 0.3420(4) 0.08509(13) 0.0303(5) Uani 1 1 d . . .
O4 O 0.5470(5) 0.3756(4) 0.20412(15) 0.0426(6) Uani 1 1 d . . .
O5 O 0.3974(5) -0.1356(4) 0.21984(15) 0.0399(6) Uani 1 1 d . . .
O6 O 0.0343(5) 0.3621(4) 0.36679(16) 0.0440(6) Uani 1 1 d . . .


_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 2.017(2) 2_665 ?
Ni1 O1 2.017(2) . ?
Ni1 O3 2.0601(19) . ?
Ni1 O3 2.0602(19) 2_665 ?
Ni1 O2 2.133(2) 2_665 ?
Ni1 O2 2.133(2) . ?
C1 O4 1.231(4) . ?
C1 O3 1.271(3) . ?
C1 C2 1.518(4) . ?
C2 N1 1.469(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 O5 1.218(4) . ?
C3 N1 1.387(4) . ?
C3 C5 1.483(4) . ?
C4 O6 1.208(4) . ?
C4 N1 1.398(4) . ?
C4 C6 1.488(4) . ?
C5 C7 1.377(4) . ?
C5 C8 1.415(4) . ?
C6 C9 1.376(4) . ?
C6 C8 1.409(4) . ?
C7 C9 1.401(4) 2_656 ?
C7 H7 0.9300 . ?
C8 C8 1.414(5) 2_656 ?
C9 C7 1.401(4) 2_656 ?
C9 H9 0.9300 . ?
O1 H1B 0.8500 . ?
O1 H1A 0.8500 . ?
O2 H2D 0.8501 . ?
O2 H2C 0.8500 . ?

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 180.0 2_665 . ?
O1 Ni1 O3 86.17(9) 2_665 . ?
O1 Ni1 O3 93.83(9) . . ?
O1 Ni1 O3 93.83(9) 2_665 2_665 ?
O1 Ni1 O3 86.17(9) . 2_665 ?
O3 Ni1 O3 180.0 . 2_665 ?
O1 Ni1 O2 90.87(14) 2_665 2_665 ?
O1 Ni1 O2 89.13(14) . 2_665 ?
O3 Ni1 O2 88.45(9) . 2_665 ?
O3 Ni1 O2 91.55(9) 2_665 2_665 ?
O1 Ni1 O2 89.13(14) 2_665 . ?
O1 Ni1 O2 90.87(14) . . ?
O3 Ni1 O2 91.55(9) . . ?
O3 Ni1 O2 88.45(9) 2_665 . ?
O2 Ni1 O2 180.0 2_665 . ?
O4 C1 O3 126.1(3) . . ?
O4 C1 C2 118.6(2) . . ?
O3 C1 C2 115.2(3) . . ?
N1 C2 C1 111.8(2) . . ?
N1 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
N1 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
O5 C3 N1 120.8(3) . . ?
O5 C3 C5 122.0(3) . . ?
N1 C3 C5 117.3(3) . . ?
O6 C4 N1 120.8(3) . . ?
O6 C4 C6 122.4(3) . . ?
N1 C4 C6 116.8(3) . . ?
C7 C5 C8 120.0(3) . . ?
C7 C5 C3 120.5(3) . . ?
C8 C5 C3 119.5(3) . . ?
C9 C6 C8 120.2(3) . . ?
C9 C6 C4 120.0(3) . . ?
C8 C6 C4 119.7(3) . . ?
C5 C7 C9 120.4(3) . 2_656 ?
C5 C7 H7 119.8 . . ?
C9 C7 H7 119.8 2_656 . ?
C6 C8 C8 119.3(3) . 2_656 ?
C6 C8 C5 121.3(3) . . ?
C8 C8 C5 119.5(3) 2_656 . ?
C6 C9 C7 120.6(3) . 2_656 ?
C6 C9 H9 119.7 . . ?
C7 C9 H9 119.7 2_656 . ?
C3 N1 C4 125.2(2) . . ?
C3 N1 C2 116.8(3) . . ?
C4 N1 C2 117.5(3) . . ?
Ni1 O1 H1B 109.1 . . ?
Ni1 O1 H1A 109.3 . . ?
H1B O1 H1A 109.5 . . ?
Ni1 O2 H2D 109.2 . . ?
Ni1 O2 H2C 109.4 . . ?
H2D O2 H2C 109.5 . . ?
C1 O3 Ni1 124.71(19) . . ?

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
O4 C1 C2 N1 -4.4(4) . . . . ?
O3 C1 C2 N1 175.3(3) . . . . ?
O5 C3 C5 C7 -2.6(5) . . . . ?
N1 C3 C5 C7 177.3(3) . . . . ?
O5 C3 C5 C8 177.3(3) . . . . ?
N1 C3 C5 C8 -2.7(4) . . . . ?
O6 C4 C6 C9 1.8(5) . . . . ?
N1 C4 C6 C9 -177.4(3) . . . . ?
O6 C4 C6 C8 -178.6(3) . . . . ?
N1 C4 C6 C8 2.1(4) . . . . ?
C8 C5 C7 C9 0.2(4) . . . 2_656 ?
C3 C5 C7 C9 -179.8(3) . . . 2_656 ?
C9 C6 C8 C8 -0.1(5) . . . 2_656 ?
C4 C6 C8 C8 -179.7(3) . . . 2_656 ?
C9 C6 C8 C5 180.0(3) . . . . ?
C4 C6 C8 C5 0.4(4) . . . . ?
C7 C5 C8 C6 179.8(3) . . . . ?
C3 C5 C8 C6 -0.2(4) . . . . ?
C7 C5 C8 C8 -0.1(5) . . . 2_656 ?
C3 C5 C8 C8 179.9(3) . . . 2_656 ?
C8 C6 C9 C7 0.0(5) . . . 2_656 ?
C4 C6 C9 C7 179.5(3) . . . 2_656 ?
O5 C3 N1 C4 -174.3(3) . . . . ?
C5 C3 N1 C4 5.8(4) . . . . ?
O5 C3 N1 C2 -2.4(4) . . . . ?
C5 C3 N1 C2 177.6(3) . . . . ?
O6 C4 N1 C3 175.3(3) . . . . ?
C6 C4 N1 C3 -5.5(4) . . . . ?
O6 C4 N1 C2 3.5(4) . . . . ?
C6 C4 N1 C2 -177.3(2) . . . . ?
C1 C2 N1 C3 -74.6(4) . . . . ?
C1 C2 N1 C4 97.9(3) . . . . ?
O4 C1 O3 Ni1 9.3(4) . . . . ?
C2 C1 O3 Ni1 -170.4(2) . . . . ?
O1 Ni1 O3 C1 165.5(2) 2_665 . . . ?
O1 Ni1 O3 C1 -14.5(2) . . . . ?
O3 Ni1 O3 C1 164(19) 2_665 . . . ?
O2 Ni1 O3 C1 -103.5(2) 2_665 . . . ?
O2 Ni1 O3 C1 76.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.075
####################################################################### 
# 
# 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_1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2089655'
loop_
_audit_author_name
_audit_author_address
'Zixin You'
;Liaoning Normal University
China
;
_audit_update_record             
;
2021-06-13 deposited with the CCDC.	2021-10-01 downloaded from the CCDC.
;
_audit_creation_date             2021-03-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H8 N2 O8, 2(C2 H8 N)'
_chemical_formula_sum            'C22 H24 N4 O8'
_chemical_formula_weight         472.45
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.8728(14)
_cell_length_b                   8.938(2)
_cell_length_c                   12.700(4)
_cell_angle_alpha                92.089(5)
_cell_angle_beta                 91.089(5)
_cell_angle_gamma                99.348(5)
_cell_volume                     545.2(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1672
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.773
_cell_measurement_theta_min      2.761
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1276 before and 0.0213 after correction.
The Ratio of minimum to maximum transmission is 0.8679.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             248
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0118
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3210
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.800
_diffrn_reflns_theta_min         1.605
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           25.0
_diffrn_source_power             1.125
_diffrn_source_voltage           45.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1915
_reflns_number_total             2282
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0553P)²+0.1528P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1140
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), N2(H2C,H2D)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
C1 C 0.8854(3) 0.21627(16) 0.63994(11) 0.0341(3) Uani 1 1 d . . . . .
C2 C 1.0642(3) 0.25545(17) 0.74066(10) 0.0328(3) Uani 1 1 d . . . . .
H2A H 1.115554 0.163299 0.767432 0.039 Uiso 1 1 calc R U . . .
H2B H 1.233786 0.322532 0.724233 0.039 Uiso 1 1 calc R U . . .
C3 C 0.7232(3) 0.23398(15) 0.87893(10) 0.0299(3) Uani 1 1 d . . . . .
C4 C 0.9547(3) 0.48752(15) 0.82818(10) 0.0275(3) Uani 1 1 d . . . . .
C5 C 0.7765(3) 0.55862(14) 0.90300(9) 0.0254(3) Uani 1 1 d . . . . .
C6 C 0.8003(3) 0.71431(15) 0.91234(10) 0.0312(3) Uani 1 1 d . . . . .
H6 H 0.926237 0.774856 0.871372 0.037 Uiso 1 1 calc R U . . .
C7 C 0.6350(3) 0.78217(15) 0.98357(11) 0.0323(3) Uani 1 1 d . . . . .
H7 H 0.653013 0.887344 0.989569 0.039 Uiso 1 1 calc R U . . .
C8 C 0.4468(3) 0.69390(14) 1.04445(10) 0.0260(3) Uani 1 1 d . . . . .
C9 C 0.4168(3) 0.53419(14) 1.03584(9) 0.0230(3) Uani 1 1 d . . . . .
N1 N 0.9169(2) 0.32925(12) 0.82244(8) 0.0284(3) Uani 1 1 d . . . . .
O1 O 0.9533(3) 0.11450(14) 0.58034(9) 0.0521(3) Uani 1 1 d . . . . .
O2 O 0.6913(3) 0.28865(15) 0.62420(9) 0.0524(3) Uani 1 1 d . . . . .
O3 O 0.6977(3) 0.09714(11) 0.86543(9) 0.0475(3) Uani 1 1 d . . . . .
O4 O 1.1267(2) 0.56293(12) 0.77555(8) 0.0411(3) Uani 1 1 d . . . . .
C10 C 0.5563(4) 0.1269(2) 0.35325(14) 0.0579(5) Uani 1 1 d . . . . .
H10A H 0.429114 0.089627 0.296009 0.087 Uiso 1 1 calc R U . . .
H10B H 0.641374 0.045235 0.378894 0.087 Uiso 1 1 calc R U . . .
H10C H 0.697510 0.204890 0.329035 0.087 Uiso 1 1 calc R U . . .
C11 C 0.3068(5) 0.3317(2) 0.41107(17) 0.0665(6) Uani 1 1 d . . . . .
H11A H 0.185360 0.312839 0.349963 0.100 Uiso 1 1 calc R U . . .
H11B H 0.463829 0.407034 0.396217 0.100 Uiso 1 1 calc R U . . .
H11C H 0.207998 0.367452 0.468984 0.100 Uiso 1 1 calc R U . . .
N2 N 0.4043(3) 0.18980(15) 0.43879(10) 0.0416(3) Uani 1 1 d . . . . .
H2C H 0.514911 0.207710 0.495969 0.050 Uiso 1 1 calc R U . . .
H2D H 0.258350 0.121360 0.454420 0.050 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
C1 C2 1.531(2) . ?
C1 O1 1.2516(17) . ?
C1 O2 1.2468(19) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 N1 1.4701(16) . ?
C3 C8 1.4855(18) 2_667 ?
C3 N1 1.3927(18) . ?
C3 O3 1.2146(17) . ?
C4 C5 1.4924(17) . ?
C4 N1 1.3956(17) . ?
C4 O4 1.2143(17) . ?
C5 C6 1.3779(19) . ?
C5 C9 1.4139(18) 2_667 ?
C6 H6 0.9300 . ?
C6 C7 1.4075(19) . ?
C7 H7 0.9300 . ?
C7 C8 1.3776(19) . ?
C8 C9 1.4110(18) . ?
C9 C9 1.417(2) 2_667 ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C10 N2 1.472(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C11 N2 1.476(2) . ?
N2 H2C 0.8900 . ?
N2 H2D 0.8900 . ?

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 C1 C2 115.74(13) . . ?
O2 C1 C2 117.87(12) . . ?
O2 C1 O1 126.38(14) . . ?
C1 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
N1 C2 C1 111.87(11) . . ?
N1 C2 H2A 109.2 . . ?
N1 C2 H2B 109.2 . . ?
N1 C3 C8 117.56(11) . 2_667 ?
O3 C3 C8 122.02(13) . 2_667 ?
O3 C3 N1 120.42(12) . . ?
N1 C4 C5 116.71(11) . . ?
O4 C4 C5 122.00(12) . . ?
O4 C4 N1 121.29(12) . . ?
C6 C5 C4 120.04(12) . . ?
C6 C5 C9 120.15(12) . 2_667 ?
C9 C5 C4 119.82(12) 2_667 . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.34(12) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.47(12) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 C3 120.29(12) . 2_667 ?
C7 C8 C9 120.33(12) . . ?
C9 C8 C3 119.37(12) . 2_667 ?
C5 C9 C9 119.49(14) 2_667 2_667 ?
C8 C9 C5 121.29(12) . 2_667 ?
C8 C9 C9 119.22(14) . 2_667 ?
C3 N1 C2 116.27(11) . . ?
C3 N1 C4 125.17(11) . . ?
C4 N1 C2 118.02(11) . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
C10 N2 C11 112.73(15) . . ?
C10 N2 H2C 109.0 . . ?
C10 N2 H2D 109.0 . . ?
C11 N2 H2C 109.0 . . ?
C11 N2 H2D 109.0 . . ?
H2C N2 H2D 107.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2C O2 0.89 1.89 2.7572(18) 164.2 . yes
N2 H2D O1 0.89 2.20 2.8761(19) 132.4 1_455 yes

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
C1 C2 N1 C3 79.01(15) . . . . ?
C1 C2 N1 C4 -93.01(14) . . . . ?
C3 C8 C9 C5 1.45(18) 2_667 . . 2_667 ?
C3 C8 C9 C9 -178.77(13) 2_667 . . 2_667 ?
C4 C5 C6 C7 -179.32(12) . . . . ?
C5 C4 N1 C2 172.76(11) . . . . ?
C5 C4 N1 C3 1.52(18) . . . . ?
C5 C6 C7 C8 -0.3(2) . . . . ?
C6 C7 C8 C3 178.78(12) . . . 2_667 ?
C6 C7 C8 C9 -0.2(2) . . . . ?
C7 C8 C9 C5 -179.54(12) . . . 2_667 ?
C7 C8 C9 C9 0.2(2) . . . 2_667 ?
C8 C3 N1 C2 -174.75(11) 2_667 . . . ?
C8 C3 N1 C4 -3.37(19) 2_667 . . . ?
C9 C5 C6 C7 0.7(2) 2_667 . . . ?
N1 C4 C5 C6 -179.45(12) . . . . ?
N1 C4 C5 C9 0.49(18) . . . 2_667 ?
O1 C1 C2 N1 -158.53(13) . . . . ?
O2 C1 C2 N1 22.41(19) . . . . ?
O3 C3 N1 C2 5.55(19) . . . . ?
O3 C3 N1 C4 176.93(13) . . . . ?
O4 C4 C5 C6 1.4(2) . . . . ?
O4 C4 C5 C9 -178.67(12) . . . 2_667 ?
O4 C4 N1 C2 -8.06(19) . . . . ?
O4 C4 N1 C3 -179.31(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2089653'
loop_
_audit_author_name
_audit_author_address
'Zixin You'
;Liaoning Normal University
China
;
_audit_update_record             
;
2021-06-13 deposited with the CCDC.	2021-10-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 Co N2 O12'
_chemical_formula_weight         511.26

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'
Co Co 0.3494 0.9721 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.0506(6)
_cell_length_b                   6.3217(6)
_cell_length_c                   15.1500(16)
_cell_angle_alpha                95.321(4)
_cell_angle_beta                 95.049(3)
_cell_angle_gamma                105.252(3)
_cell_volume                     461.47(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1044
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      29.83

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.33
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.840
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             261
_exptl_absorpt_coefficient_mu    1.009
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6068
_exptl_absorpt_correction_T_max  0.7319
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            2389
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.36
_diffrn_reflns_theta_max         24.99
_reflns_number_total             1616
_reflns_number_gt                1443
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0234P)²+1.0636P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1616
_refine_ls_number_parameters     151
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.0942
_refine_ls_wR_factor_gt          0.0854
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.085
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.5000 0.0000 1.0000 0.0209(2) Uani 1 2 d S . .
C1 C 0.6894(7) 0.1977(6) 0.8352(2) 0.0250(7) Uani 1 1 d U . .
C2 C 0.9117(7) 0.3476(7) 0.7912(2) 0.0343(9) Uani 1 1 d . . .
H2A H 0.9915 0.4841 0.8305 0.041 Uiso 1 1 calc R . .
H2B H 1.0574 0.2768 0.7821 0.041 Uiso 1 1 calc R . .
C3 C 0.8364(7) 0.2745(6) 0.6274(2) 0.0296(8) Uani 1 1 d . . .
C4 C 0.7125(7) 0.3210(6) 0.5415(2) 0.0252(8) Uani 1 1 d . . .
C5 C 0.7470(7) 0.2123(6) 0.4625(2) 0.0305(8) Uani 1 1 d . . .
H5 H 0.8479 0.1087 0.4632 0.037 Uiso 1 1 calc R . .
C6 C 0.6321(7) 0.2553(6) 0.3805(2) 0.0303(8) Uani 1 1 d . . .
H6 H 0.6582 0.1808 0.3275 0.036 Uiso 1 1 calc R . .
C7 C 0.4806(7) 0.4077(5) 0.3783(2) 0.0251(7) Uani 1 1 d . . .
C8 C 0.4421(7) 0.5215(5) 0.4588(2) 0.0244(7) Uani 1 1 d . . .
C9 C 0.3585(7) 0.4527(6) 0.2921(2) 0.0279(8) Uani 1 1 d . . .
N1 N 0.8018(6) 0.3984(5) 0.70488(19) 0.0298(7) Uani 1 1 d . . .
O1 O 0.6371(7) -0.2950(5) 0.9676(2) 0.0671(11) Uani 1 1 d . . .
H1A H 0.4657 -0.3593 0.9551 0.081 Uiso 1 1 d R . .
H1B H 0.6585 -0.3154 0.9128 0.081 Uiso 1 1 d R . .
O2 O 0.8260(5) 0.1097(7) 1.09831(18) 0.0665(11) Uani 1 1 d . . .
H2D H 0.9768 0.0743 1.0968 0.080 Uiso 1 1 d R . .
H2C H 0.7383 0.0497 1.1390 0.080 Uiso 1 1 d R . .
O3 O 0.7656(5) 0.1570(4) 0.91281(15) 0.0318(6) Uani 1 1 d . . .
O4 O 0.4573(6) 0.1253(4) 0.79462(17) 0.0432(7) Uani 1 1 d . . .
O5 O 0.9660(6) 0.1386(5) 0.63207(18) 0.0440(7) Uani 1 1 d . . .
O6 O 0.3941(6) 0.3646(5) 0.22086(17) 0.0400(7) Uani 1 1 d . . .


_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
Co1 O2 2.046(3) . ?
Co1 O2 2.046(3) 2_657 ?
Co1 O3 2.094(2) . ?
Co1 O3 2.094(2) 2_657 ?
Co1 O1 2.183(3) . ?
Co1 O1 2.183(3) 2_657 ?
C1 O4 1.224(4) . ?
C1 O3 1.275(4) . ?
C1 C2 1.514(5) . ?
C2 N1 1.471(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 O5 1.212(4) . ?
C3 N1 1.399(5) . ?
C3 C4 1.482(5) . ?
C4 C5 1.373(5) . ?
C4 C8 1.418(5) 2_666 ?
C5 C6 1.405(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.380(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.413(5) . ?
C7 C9 1.479(5) . ?
C8 C8 1.410(6) 2_666 ?
C8 C4 1.418(5) 2_666 ?
C9 O6 1.218(4) . ?
C9 N1 1.394(5) 2_666 ?
N1 C9 1.394(5) 2_666 ?
O1 H1A 0.8500 . ?
O1 H1B 0.8500 . ?
O2 H2D 0.8500 . ?
O2 H2C 0.8500 . ?

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 Co1 O2 179.999(1) . 2_657 ?
O2 Co1 O3 87.08(11) . . ?
O2 Co1 O3 92.92(10) 2_657 . ?
O2 Co1 O3 92.92(10) . 2_657 ?
O2 Co1 O3 87.08(11) 2_657 2_657 ?
O3 Co1 O3 179.999(1) . 2_657 ?
O2 Co1 O1 89.14(16) . . ?
O2 Co1 O1 90.86(16) 2_657 . ?
O3 Co1 O1 88.02(10) . . ?
O3 Co1 O1 91.98(10) 2_657 . ?
O2 Co1 O1 90.86(16) . 2_657 ?
O2 Co1 O1 89.14(16) 2_657 2_657 ?
O3 Co1 O1 91.98(10) . 2_657 ?
O3 Co1 O1 88.01(10) 2_657 2_657 ?
O1 Co1 O1 180.000(2) . 2_657 ?
O4 C1 O3 125.7(3) . . ?
O4 C1 C2 118.9(3) . . ?
O3 C1 C2 115.4(3) . . ?
N1 C2 C1 111.8(3) . . ?
N1 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
N1 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
O5 C3 N1 120.4(3) . . ?
O5 C3 C4 122.8(3) . . ?
N1 C3 C4 116.9(3) . . ?
C5 C4 C8 120.0(3) . 2_666 ?
C5 C4 C3 120.2(3) . . ?
C8 C4 C3 119.8(3) 2_666 . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C7 C6 C5 120.2(3) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 119.9(3) . . ?
C6 C7 C9 120.3(3) . . ?
C8 C7 C9 119.8(3) . . ?
C8 C8 C7 119.9(4) 2_666 . ?
C8 C8 C4 119.1(4) 2_666 2_666 ?
C7 C8 C4 121.0(3) . 2_666 ?
O6 C9 N1 120.6(3) . 2_666 ?
O6 C9 C7 122.2(3) . . ?
N1 C9 C7 117.2(3) 2_666 . ?
C9 N1 C3 125.1(3) 2_666 . ?
C9 N1 C2 116.6(3) 2_666 . ?
C3 N1 C2 117.8(3) . . ?
Co1 O1 H1A 84.6 . . ?
Co1 O1 H1B 112.4 . . ?
H1A O1 H1B 89.7 . . ?
Co1 O2 H2D 123.5 . . ?
Co1 O2 H2C 95.0 . . ?
H2D O2 H2C 109.9 . . ?
C1 O3 Co1 125.1(2) . . ?

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
O4 C1 C2 N1 4.5(5) . . . . ?
O3 C1 C2 N1 -176.0(3) . . . . ?
O5 C3 C4 C5 -1.5(6) . . . . ?
N1 C3 C4 C5 177.4(3) . . . . ?
O5 C3 C4 C8 178.5(3) . . . 2_666 ?
N1 C3 C4 C8 -2.5(5) . . . 2_666 ?
C8 C4 C5 C6 0.3(5) 2_666 . . . ?
C3 C4 C5 C6 -179.7(3) . . . . ?
C4 C5 C6 C7 -0.3(6) . . . . ?
C5 C6 C7 C8 0.3(5) . . . . ?
C5 C6 C7 C9 -179.8(3) . . . . ?
C6 C7 C8 C8 -0.2(6) . . . 2_666 ?
C9 C7 C8 C8 179.9(4) . . . 2_666 ?
C6 C7 C8 C4 179.9(3) . . . 2_666 ?
C9 C7 C8 C4 0.0(5) . . . 2_666 ?
C6 C7 C9 O6 -2.6(5) . . . . ?
C8 C7 C9 O6 177.4(3) . . . . ?
C6 C7 C9 N1 177.3(3) . . . 2_666 ?
C8 C7 C9 N1 -2.7(5) . . . 2_666 ?
O5 C3 N1 C9 -175.3(3) . . . 2_666 ?
C4 C3 N1 C9 5.7(5) . . . 2_666 ?
O5 C3 N1 C2 -3.9(5) . . . . ?
C4 C3 N1 C2 177.2(3) . . . . ?
C1 C2 N1 C9 74.4(4) . . . 2_666 ?
C1 C2 N1 C3 -97.8(4) . . . . ?
O4 C1 O3 Co1 -10.9(5) . . . . ?
C2 C1 O3 Co1 169.6(2) . . . . ?
O2 Co1 O3 C1 -165.6(3) . . . . ?
O2 Co1 O3 C1 14.4(3) 2_657 . . . ?
O3 Co1 O3 C1 -122(13) 2_657 . . . ?
O1 Co1 O3 C1 105.2(3) . . . . ?
O1 Co1 O3 C1 -74.8(3) 2_657 . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.082
