# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2174117'
loop_
_audit_author_name
_audit_author_address
'Yu Xinyu'
;Beijing Institute of Technolog
China
;
_audit_update_record             
;
2022-05-22 deposited with the CCDC.	2023-05-22 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         ?
_chemical_formula_sum            'C23 H24 Cu N6 O6'
_chemical_formula_weight         544.02

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'
Cu Cu 0.3201 1.2651 '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'

_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                   7.3115(3)
_cell_length_b                   16.1712(8)
_cell_length_c                   20.4372(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2416.41(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    46186
_cell_measurement_theta_min      2.358
_cell_measurement_theta_max      30.436

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_F_000             1124
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.955
_shelx_estimated_absorpt_T_min   0.796
_shelx_estimated_absorpt_T_max   0.817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.795
_exptl_absorpt_correction_T_max  0.816
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Smart Apex CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            46186
_diffrn_reflns_av_unetI/netI     0.0719
_diffrn_reflns_av_R_equivalents  0.0768
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.358
_diffrn_reflns_theta_max         30.436
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7311
_reflns_number_gt                5265
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.999

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0306P)²+0.0788P] 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 1848 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.009(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7311
_refine_ls_number_parameters     334
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.0718
_refine_ls_wR_factor_gt          0.0624
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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
Cu1 Cu 0.41461(5) 0.35914(2) 0.52481(2) 0.02019(9) Uani 1 1 d . . . . .
O1 O 0.5030(3) 0.49165(19) 0.41299(13) 0.0527(8) Uani 1 1 d . . . . .
N1 N -0.1552(3) 0.56884(15) 0.21762(11) 0.0227(5) Uani 1 1 d . . . . .
C1 C 0.3423(5) 0.4670(2) 0.41499(14) 0.0276(7) Uani 1 1 d . . . . .
O2 O 0.2794(3) 0.41335(13) 0.45453(9) 0.0292(5) Uani 1 1 d . . . . .
C8 C -0.4005(5) 0.5989(2) 0.16175(14) 0.0318(7) Uani 1 1 d . . . . .
H8 H -0.515472 0.618971 0.150497 0.038 Uiso 1 1 calc R U . . .
C2 C 0.2067(4) 0.50184(19) 0.36712(14) 0.0241(7) Uani 1 1 d . . . . .
O3 O 0.0138(3) 0.20391(13) 0.40086(10) 0.0278(5) Uani 1 1 d . . . . .
N3 N 0.1037(4) 0.43227(15) 0.14903(10) 0.0264(5) Uani 1 1 d . . . . .
C3 C 0.2685(4) 0.5478(2) 0.31431(15) 0.0320(7) Uani 1 1 d . . . . .
H3 H 0.391623 0.561853 0.311522 0.038 Uiso 1 1 calc R U . . .
O4 O -0.2794(3) 0.22167(15) 0.37639(10) 0.0368(6) Uani 1 1 d . . . . .
C12 C 0.2672(5) 0.4827(2) 0.06900(15) 0.0300(7) Uani 1 1 d . . . . .
H12 H 0.357551 0.489425 0.037415 0.036 Uiso 1 1 calc R U . . .
C4 C 0.1495(4) 0.5730(2) 0.26581(14) 0.0293(7) Uani 1 1 d . . . . .
H4 H 0.191678 0.603410 0.230255 0.035 Uiso 1 1 calc R U . . .
O5 O 0.5749(7) 0.7284(2) 0.36484(17) 0.0973(13) Uani 1 1 d . . . . .
N5 N 0.4084(4) 0.25640(14) 0.47125(11) 0.0302(5) Uani 1 1 d . . . . .
H5A H 0.418109 0.212564 0.497349 0.045 Uiso 1 1 calc R U . . .
H5B H 0.501019 0.256784 0.443007 0.045 Uiso 1 1 calc R U . . .
H5C H 0.303157 0.253895 0.449429 0.045 Uiso 1 1 calc R U . . .
C5 C -0.0335(4) 0.55230(19) 0.27094(14) 0.0236(7) Uani 1 1 d . . . . .
O6 O 0.7163(3) 0.39663(14) 0.48863(10) 0.0348(6) Uani 1 1 d D . . . .
H1 H 0.752(5) 0.422(2) 0.5233(12) 0.052 Uiso 1 1 d D U . . .
H1B H 0.671(5) 0.430(2) 0.4633(14) 0.052 Uiso 1 1 d D U . . .
C6 C -0.0995(5) 0.51010(18) 0.32482(13) 0.0261(6) Uani 1 1 d . . . . .
H6 H -0.223789 0.498941 0.328863 0.031 Uiso 1 1 calc R U . . .
N7 N 0.7491(7) 0.6734(2) 0.44591(19) 0.0676(11) Uani 1 1 d . . . . .
C7 C 0.0222(4) 0.4847(2) 0.37268(14) 0.0267(7) Uani 1 1 d . . . . .
H7 H -0.020708 0.455833 0.408928 0.032 Uiso 1 1 calc R U . . .
C9 C -0.3239(4) 0.6057(2) 0.22205(15) 0.0293(7) Uani 1 1 d . . . . .
H9 H -0.375269 0.630381 0.258843 0.035 Uiso 1 1 calc R U . . .
N2 N -0.2853(3) 0.55854(16) 0.11989(11) 0.0269(6) Uani 1 1 d . . . . .
C10 C -0.1385(4) 0.54196(18) 0.15471(13) 0.0214(6) Uani 1 1 d . . . . .
C11 C 0.0262(4) 0.50398(18) 0.12792(13) 0.0214(6) Uani 1 1 d . . . . .
N4 N 0.1216(3) 0.53554(14) 0.07877(11) 0.0211(5) Uani 1 1 d . . . . .
C13 C 0.2588(5) 0.4198(2) 0.11211(14) 0.0326(8) Uani 1 1 d . . . . .
H13 H 0.341606 0.376495 0.116165 0.039 Uiso 1 1 calc R U . . .
C14 C 0.0461(4) 0.37995(17) 0.20206(14) 0.0268(7) Uani 1 1 d . . . . .
C15 C -0.1349(4) 0.3579(2) 0.20862(14) 0.0328(7) Uani 1 1 d . . . . .
H15 H -0.221309 0.375105 0.178113 0.039 Uiso 1 1 calc R U . . .
C16 C -0.1859(5) 0.3094(2) 0.26177(15) 0.0331(8) Uani 1 1 d . . . . .
H16 H -0.308016 0.294799 0.267187 0.040 Uiso 1 1 calc R U . . .
C17 C -0.0575(4) 0.28271(17) 0.30662(13) 0.0245(7) Uani 1 1 d . . . . .
C18 C 0.1255(4) 0.30274(18) 0.29711(14) 0.0269(7) Uani 1 1 d . . . . .
H18 H 0.213632 0.282784 0.325862 0.032 Uiso 1 1 calc R U . . .
C19 C 0.1767(4) 0.3519(2) 0.24538(14) 0.0282(7) Uani 1 1 d . . . . .
H19 H 0.298859 0.366212 0.239626 0.034 Uiso 1 1 calc R U . . .
C20 C -0.1153(4) 0.23301(17) 0.36545(13) 0.0233(7) Uani 1 1 d . . . . .
C21 C 0.7528(10) 0.6230(3) 0.5044(2) 0.0971(18) Uani 1 1 d . . . . .
H21A H 0.631304 0.604137 0.514126 0.146 Uiso 1 1 calc R U . . .
H21B H 0.798236 0.655158 0.540348 0.146 Uiso 1 1 calc R U . . .
H21C H 0.831251 0.576203 0.497436 0.146 Uiso 1 1 calc R U . . .
C22 C 0.9153(10) 0.7056(3) 0.4199(3) 0.0995(18) Uani 1 1 d . . . . .
H22A H 0.899551 0.717395 0.374160 0.149 Uiso 1 1 calc R U . . .
H22B H 1.011209 0.665662 0.425273 0.149 Uiso 1 1 calc R U . . .
H22C H 0.947178 0.755556 0.442584 0.149 Uiso 1 1 calc R U . . .
C23 C 0.5940(10) 0.6866(3) 0.4145(2) 0.0747(14) Uani 1 1 d . . . . .
H23 H 0.489500 0.661910 0.431621 0.090 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
Cu1 O2 1.952(2) . ?
Cu1 O3 1.968(2) 4_556 ?
Cu1 N5 1.990(2) . ?
Cu1 N4 2.046(2) 2_565 ?
Cu1 O6 2.404(2) . ?
O1 C1 1.241(4) . ?
N1 C10 1.363(3) . ?
N1 C9 1.373(4) . ?
N1 C5 1.432(4) . ?
C1 O2 1.272(4) . ?
C1 C2 1.502(4) . ?
C8 C9 1.358(4) . ?
C8 N2 1.367(4) . ?
C8 H8 0.9300 . ?
C2 C7 1.382(4) . ?
C2 C3 1.387(4) . ?
O3 C20 1.279(4) . ?
N3 C11 1.361(4) . ?
N3 C13 1.377(4) . ?
N3 C14 1.438(3) . ?
C3 C4 1.380(4) . ?
C3 H3 0.9300 . ?
O4 C20 1.234(4) . ?
C12 C13 1.346(4) . ?
C12 N4 1.380(4) . ?
C12 H12 0.9300 . ?
C4 C5 1.383(4) . ?
C4 H4 0.9300 . ?
O5 C23 1.227(6) . ?
N5 H5A 0.8900 . ?
N5 H5B 0.8900 . ?
N5 H5C 0.8900 . ?
C5 C6 1.382(4) . ?
O6 H1 0.86(2) . ?
O6 H1B 0.82(2) . ?
C6 C7 1.385(4) . ?
C6 H6 0.9300 . ?
N7 C23 1.321(7) . ?
N7 C22 1.425(7) . ?
N7 C21 1.447(6) . ?
C7 H7 0.9300 . ?
C9 H9 0.9300 . ?
N2 C10 1.316(4) . ?
C10 C11 1.458(4) . ?
C11 N4 1.325(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.377(4) . ?
C14 C19 1.379(4) . ?
C15 C16 1.391(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.381(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.390(4) . ?
C17 C20 1.507(4) . ?
C18 C19 1.375(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O3 170.92(10) . 4_556 ?
O2 Cu1 N5 87.62(10) . . ?
O3 Cu1 N5 90.04(9) 4_556 . ?
O2 Cu1 N4 87.55(9) . 2_565 ?
O3 Cu1 N4 93.60(9) 4_556 2_565 ?
N5 Cu1 N4 171.25(11) . 2_565 ?
O2 Cu1 O6 97.18(8) . . ?
O3 Cu1 O6 91.72(8) 4_556 . ?
N5 Cu1 O6 93.58(10) . . ?
N4 Cu1 O6 94.26(9) 2_565 . ?
C10 N1 C9 106.4(2) . . ?
C10 N1 C5 127.0(2) . . ?
C9 N1 C5 126.1(2) . . ?
O1 C1 O2 125.6(3) . . ?
O1 C1 C2 118.9(3) . . ?
O2 C1 C2 115.5(3) . . ?
C1 O2 Cu1 126.2(2) . . ?
C9 C8 N2 110.7(3) . . ?
C9 C8 H8 124.7 . . ?
N2 C8 H8 124.7 . . ?
C7 C2 C3 119.3(3) . . ?
C7 C2 C1 121.0(3) . . ?
C3 C2 C1 119.5(3) . . ?
C20 O3 Cu1 110.81(19) . 4_456 ?
C11 N3 C13 107.1(2) . . ?
C11 N3 C14 128.2(2) . . ?
C13 N3 C14 124.7(3) . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C13 C12 N4 109.7(3) . . ?
C13 C12 H12 125.1 . . ?
N4 C12 H12 125.1 . . ?
C3 C4 C5 118.9(3) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
Cu1 N5 H5A 109.5 . . ?
Cu1 N5 H5B 109.5 . . ?
H5A N5 H5B 109.5 . . ?
Cu1 N5 H5C 109.5 . . ?
H5A N5 H5C 109.5 . . ?
H5B N5 H5C 109.5 . . ?
C6 C5 C4 121.2(3) . . ?
C6 C5 N1 118.8(3) . . ?
C4 C5 N1 119.9(3) . . ?
Cu1 O6 H1 98(3) . . ?
Cu1 O6 H1B 90(3) . . ?
H1 O6 H1B 109(3) . . ?
C5 C6 C7 119.0(3) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C23 N7 C22 119.5(5) . . ?
C23 N7 C21 120.5(5) . . ?
C22 N7 C21 119.9(5) . . ?
C2 C7 C6 120.6(3) . . ?
C2 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C8 C9 N1 106.0(3) . . ?
C8 C9 H9 127.0 . . ?
N1 C9 H9 127.0 . . ?
C10 N2 C8 105.2(2) . . ?
N2 C10 N1 111.8(2) . . ?
N2 C10 C11 123.8(2) . . ?
N1 C10 C11 124.3(2) . . ?
N4 C11 N3 110.4(3) . . ?
N4 C11 C10 123.8(3) . . ?
N3 C11 C10 125.7(3) . . ?
C11 N4 C12 106.1(2) . . ?
C11 N4 Cu1 131.4(2) . 2_564 ?
C12 N4 Cu1 122.51(19) . 2_564 ?
C12 C13 N3 106.6(3) . . ?
C12 C13 H13 126.7 . . ?
N3 C13 H13 126.7 . . ?
C15 C14 C19 121.2(3) . . ?
C15 C14 N3 120.5(3) . . ?
C19 C14 N3 118.3(3) . . ?
C14 C15 C16 118.7(3) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
C17 C16 C15 120.8(3) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 119.2(3) . . ?
C16 C17 C20 120.4(3) . . ?
C18 C17 C20 120.4(3) . . ?
C19 C18 C17 120.3(3) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C14 119.7(3) . . ?
C18 C19 H19 120.2 . . ?
C14 C19 H19 120.2 . . ?
O4 C20 O3 124.1(3) . . ?
O4 C20 C17 119.8(3) . . ?
O3 C20 C17 116.1(3) . . ?
N7 C21 H21A 109.5 . . ?
N7 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N7 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N7 C22 H22A 109.5 . . ?
N7 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N7 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O5 C23 N7 126.0(6) . . ?
O5 C23 H23 117.0 . . ?
N7 C23 H23 117.0 . . ?

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
O1 C1 O2 Cu1 3.0(5) . . . . ?
C2 C1 O2 Cu1 -177.43(19) . . . . ?
O1 C1 C2 C7 -171.5(3) . . . . ?
O2 C1 C2 C7 8.8(4) . . . . ?
O1 C1 C2 C3 12.3(5) . . . . ?
O2 C1 C2 C3 -167.3(3) . . . . ?
C7 C2 C3 C4 -3.2(5) . . . . ?
C1 C2 C3 C4 173.0(3) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
C3 C4 C5 C6 2.7(5) . . . . ?
C3 C4 C5 N1 -172.4(3) . . . . ?
C10 N1 C5 C6 -118.6(3) . . . . ?
C9 N1 C5 C6 52.1(4) . . . . ?
C10 N1 C5 C4 56.6(4) . . . . ?
C9 N1 C5 C4 -132.7(3) . . . . ?
C4 C5 C6 C7 -3.3(5) . . . . ?
N1 C5 C6 C7 171.9(3) . . . . ?
C3 C2 C7 C6 2.6(5) . . . . ?
C1 C2 C7 C6 -173.5(3) . . . . ?
C5 C6 C7 C2 0.6(5) . . . . ?
N2 C8 C9 N1 0.3(4) . . . . ?
C10 N1 C9 C8 0.3(3) . . . . ?
C5 N1 C9 C8 -172.0(3) . . . . ?
C9 C8 N2 C10 -0.8(4) . . . . ?
C8 N2 C10 N1 0.9(3) . . . . ?
C8 N2 C10 C11 -175.5(3) . . . . ?
C9 N1 C10 N2 -0.8(3) . . . . ?
C5 N1 C10 N2 171.4(3) . . . . ?
C9 N1 C10 C11 175.7(3) . . . . ?
C5 N1 C10 C11 -12.1(5) . . . . ?
C13 N3 C11 N4 1.8(3) . . . . ?
C14 N3 C11 N4 178.3(3) . . . . ?
C13 N3 C11 C10 -178.3(3) . . . . ?
C14 N3 C11 C10 -1.7(5) . . . . ?
N2 C10 C11 N4 57.7(4) . . . . ?
N1 C10 C11 N4 -118.4(3) . . . . ?
N2 C10 C11 N3 -122.3(3) . . . . ?
N1 C10 C11 N3 61.7(4) . . . . ?
N3 C11 N4 C12 -1.1(3) . . . . ?
C10 C11 N4 C12 178.9(3) . . . . ?
N3 C11 N4 Cu1 -179.51(19) . . . 2_564 ?
C10 C11 N4 Cu1 0.5(4) . . . 2_564 ?
C13 C12 N4 C11 0.0(4) . . . . ?
C13 C12 N4 Cu1 178.6(2) . . . 2_564 ?
N4 C12 C13 N3 1.0(4) . . . . ?
C11 N3 C13 C12 -1.7(4) . . . . ?
C14 N3 C13 C12 -178.4(3) . . . . ?
C11 N3 C14 C15 46.9(4) . . . . ?
C13 N3 C14 C15 -137.0(3) . . . . ?
C11 N3 C14 C19 -133.8(3) . . . . ?
C13 N3 C14 C19 42.2(4) . . . . ?
C19 C14 C15 C16 2.8(5) . . . . ?
N3 C14 C15 C16 -178.0(3) . . . . ?
C14 C15 C16 C17 -1.0(5) . . . . ?
C15 C16 C17 C18 -1.9(5) . . . . ?
C15 C16 C17 C20 177.6(3) . . . . ?
C16 C17 C18 C19 3.1(5) . . . . ?
C20 C17 C18 C19 -176.4(3) . . . . ?
C17 C18 C19 C14 -1.4(5) . . . . ?
C15 C14 C19 C18 -1.7(5) . . . . ?
N3 C14 C19 C18 179.1(3) . . . . ?
Cu1 O3 C20 O4 -1.0(3) 4_456 . . . ?
Cu1 O3 C20 C17 -179.95(18) 4_456 . . . ?
C16 C17 C20 O4 -5.7(4) . . . . ?
C18 C17 C20 O4 173.8(3) . . . . ?
C16 C17 C20 O3 173.3(3) . . . . ?
C18 C17 C20 O3 -7.2(4) . . . . ?
C22 N7 C23 O5 -3.6(7) . . . . ?
C21 N7 C23 O5 179.7(4) . . . . ?

_refine_diff_density_max         0.334
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.071



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DMF NH3`H2O'
####################################################################### 
# 
# 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_pl
_database_code_depnum_ccdc_archive 'CCDC 2174118'
loop_
_audit_author_name
_audit_author_address
'Yu Xinyu'
;Beijing Institute of Technolog
China
;
_audit_update_record             
;
2022-05-22 deposited with the CCDC.	2023-05-22 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         ?
_chemical_formula_sum            'C23 H24 N6 Ni O6'
_chemical_formula_weight         539.19

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'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   7.4327(8)
_cell_length_b                   20.826(2)
_cell_length_c                   16.1134(16)
_cell_angle_alpha                90
_cell_angle_beta                 100.733(4)
_cell_angle_gamma                90
_cell_volume                     2450.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    21054
_cell_measurement_theta_min      2.341
_cell_measurement_theta_max      28.339

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.843
_shelx_estimated_absorpt_T_min   0.811
_shelx_estimated_absorpt_T_max   0.850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.810
_exptl_absorpt_correction_T_max  0.849
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Smart Apex CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21054
_diffrn_reflns_av_unetI/netI     0.0807
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.341
_diffrn_reflns_theta_max         28.339
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             6032
_reflns_number_gt                3924
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1084P)²+2.5287P] 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_number_reflns         6032
_refine_ls_number_parameters     334
_refine_ls_number_restraints     74
_refine_ls_R_factor_all          0.1092
_refine_ls_R_factor_gt           0.0633
_refine_ls_wR_factor_ref         0.1927
_refine_ls_wR_factor_gt          0.1665
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.057
_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 0.22957(6) 0.02874(2) -0.11541(3) 0.01995(16) Uani 1 1 d . . . . .
O1 O 0.3480(4) 0.10938(12) -0.04501(17) 0.0272(6) Uani 1 1 d . . . . .
O2 O 0.0565(4) 0.08724(13) -0.05186(17) 0.0275(6) Uani 1 1 d . . . . .
O3 O -0.0635(4) 0.04114(12) 0.17379(17) 0.0278(6) Uani 1 1 d . . . . .
O4 O -0.2470(5) 0.08534(19) 0.2521(3) 0.0661(12) Uani 1 1 d . . . . .
N1 N 0.4319(4) 0.27858(15) 0.3140(2) 0.0274(7) Uani 1 1 d . . . . .
N2 N 0.5489(5) 0.37553(16) 0.3007(2) 0.0287(7) Uani 1 1 d . . . . .
N3 N 0.1444(4) 0.41465(15) 0.2757(2) 0.0250(7) Uani 1 1 d . . . . .
N4 N 0.1081(5) 0.34184(16) 0.1746(2) 0.0303(8) Uani 1 1 d . . . . .
C1 C 0.1942(5) 0.12201(18) -0.0257(2) 0.0239(8) Uani 1 1 d . . . . .
C2 C 0.1745(6) 0.18078(18) 0.0257(2) 0.0268(8) Uani 1 1 d . . . . .
C3 C 0.3192(6) 0.2220(2) 0.0500(3) 0.0316(9) Uani 1 1 d . . . . .
H3 H 0.430634 0.213793 0.033715 0.038 Uiso 1 1 calc R U . . .
C4 C 0.3005(6) 0.2762(2) 0.0989(3) 0.0335(9) Uani 1 1 d . . . . .
H4 H 0.398075 0.304313 0.114803 0.040 Uiso 1 1 calc R U . . .
O6 O 0.3870(12) 0.6331(4) -0.0074(6) 0.181(3) Uani 1 1 d D U . . .
N5 N 0.2835(5) -0.02893(15) -0.0098(2) 0.0288(7) Uani 1 1 d . . . . .
H5A H 0.179175 -0.045370 0.000318 0.043 Uiso 1 1 calc R U . . .
H5B H 0.336482 -0.005700 0.034419 0.043 Uiso 1 1 calc R U . . .
H5C H 0.358137 -0.060624 -0.018489 0.043 Uiso 1 1 calc R U . . .
C5 C 0.1339(6) 0.28724(19) 0.1233(2) 0.0294(9) Uani 1 1 d . . . . .
O5 O 0.4631(4) -0.00256(13) -0.15852(18) 0.0293(6) Uani 1 1 d D . . . .
H1 H 0.419(7) -0.0274(16) -0.198(2) 0.044 Uiso 1 1 d D U . . .
H1B H 0.491(7) 0.0321(13) -0.180(3) 0.044 Uiso 1 1 d D U . . .
C6 C -0.0134(6) 0.2468(2) 0.0972(3) 0.0337(10) Uani 1 1 d . . . . .
H6 H -0.125899 0.255428 0.112188 0.040 Uiso 1 1 calc R U . . .
N7 N 0.6403(18) 0.5680(6) -0.0221(8) 0.180(4) Uani 1 1 d D U . . .
C7 C 0.0071(6) 0.1936(2) 0.0490(3) 0.0321(9) Uani 1 1 d . . . . .
H7 H -0.091448 0.166139 0.031999 0.038 Uiso 1 1 calc R U . . .
C8 C -0.0496(6) 0.3783(2) 0.1622(3) 0.0369(10) Uani 1 1 d . . . . .
H8 H -0.152152 0.373290 0.119822 0.044 Uiso 1 1 calc R U . . .
C9 C -0.0242(6) 0.4227(2) 0.2244(3) 0.0346(10) Uani 1 1 d . . . . .
H9 H -0.108589 0.454287 0.231582 0.041 Uiso 1 1 calc R U . . .
C10 C 0.2211(5) 0.36506(17) 0.2444(2) 0.0239(8) Uani 1 1 d . . . . .
C11 C 0.3998(5) 0.33996(18) 0.2839(2) 0.0248(8) Uani 1 1 d . . . . .
C12 C 0.6822(6) 0.3364(2) 0.3444(3) 0.0365(10) Uani 1 1 d . . . . .
H12 H 0.802345 0.348795 0.365117 0.044 Uiso 1 1 calc R U . . .
C13 C 0.6127(6) 0.2761(2) 0.3530(3) 0.0359(10) Uani 1 1 d . . . . .
H13 H 0.675129 0.240884 0.379849 0.043 Uiso 1 1 calc R U . . .
C14 C 0.3046(5) 0.22577(18) 0.3007(3) 0.0270(8) Uani 1 1 d . . . . .
C15 C 0.1339(6) 0.23263(19) 0.3224(3) 0.0325(9) Uani 1 1 d . . . . .
H15 H 0.105631 0.269009 0.350871 0.039 Uiso 1 1 calc R U . . .
C16 C 0.0065(6) 0.1844(2) 0.3009(3) 0.0352(10) Uani 1 1 d . . . . .
H16 H -0.108059 0.188164 0.315713 0.042 Uiso 1 1 calc R U . . .
C17 C 0.0471(6) 0.13016(19) 0.2572(3) 0.0291(9) Uani 1 1 d . . . . .
C18 C 0.2202(6) 0.12359(19) 0.2390(3) 0.0325(9) Uani 1 1 d . . . . .
H18 H 0.250201 0.086910 0.211636 0.039 Uiso 1 1 calc R U . . .
C19 C 0.3509(6) 0.17186(19) 0.2617(3) 0.0311(9) Uani 1 1 d . . . . .
H19 H 0.468255 0.167195 0.250165 0.037 Uiso 1 1 calc R U . . .
C20 C -0.1006(6) 0.08191(19) 0.2252(3) 0.0314(9) Uani 1 1 d . . . . .
C21 C 0.540(2) 0.6144(7) 0.0210(11) 0.247(7) Uani 1 1 d D U . . .
H21 H 0.597767 0.630349 0.073154 0.296 Uiso 1 1 calc R U . . .
C22 C 0.821(2) 0.5501(8) 0.0167(11) 0.230(7) Uani 1 1 d D U . . .
H22A H 0.847270 0.508067 -0.002277 0.346 Uiso 1 1 calc R U . . .
H22B H 0.829955 0.549662 0.076943 0.346 Uiso 1 1 calc R U . . .
H22C H 0.906404 0.580425 0.001755 0.346 Uiso 1 1 calc R U . . .
C23 C 0.526(2) 0.5374(6) -0.1035(8) 0.224(6) Uani 1 1 d D U . . .
H23A H 0.491169 0.494551 -0.091202 0.336 Uiso 1 1 calc R U . . .
H23B H 0.599029 0.535954 -0.146839 0.336 Uiso 1 1 calc R U . . .
H23C H 0.418676 0.562704 -0.122469 0.336 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 O3 2.023(3) 3 ?
Ni1 N5 2.060(3) . ?
Ni1 O5 2.090(3) . ?
Ni1 N3 2.110(3) 4_565 ?
Ni1 O1 2.124(3) . ?
Ni1 O2 2.163(3) . ?
Ni1 C1 2.464(4) . ?
O1 C1 1.267(5) . ?
O2 C1 1.260(5) . ?
O3 C20 1.252(5) . ?
O4 C20 1.246(5) . ?
N1 C11 1.372(5) . ?
N1 C13 1.375(5) . ?
N1 C14 1.441(5) . ?
N2 C11 1.319(5) . ?
N2 C12 1.373(6) . ?
N3 C10 1.324(5) . ?
N3 C9 1.377(5) . ?
N4 C10 1.361(5) . ?
N4 C8 1.379(5) . ?
N4 C5 1.439(5) . ?
C1 C2 1.501(5) . ?
C2 C3 1.375(6) . ?
C2 C7 1.391(6) . ?
C3 C4 1.398(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(6) . ?
C4 H4 0.9300 . ?
O6 C21 1.208(13) . ?
N5 H5A 0.8900 . ?
N5 H5B 0.8900 . ?
N5 H5C 0.8900 . ?
C5 C6 1.384(6) . ?
O5 H1 0.838(19) . ?
O5 H1B 0.846(19) . ?
C6 C7 1.377(6) . ?
C6 H6 0.9300 . ?
N7 C22 1.419(13) . ?
N7 C21 1.472(13) . ?
N7 C23 1.558(13) . ?
C7 H7 0.9300 . ?
C8 C9 1.352(6) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.458(5) . ?
C12 C13 1.374(6) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C19 1.362(5) . ?
C14 C15 1.385(6) . ?
C15 C16 1.379(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.394(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.378(6) . ?
C17 C20 1.507(5) . ?
C18 C19 1.398(6) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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
O3 Ni1 N5 88.44(12) 3 . ?
O3 Ni1 O5 95.37(11) 3 . ?
N5 Ni1 O5 92.68(12) . . ?
O3 Ni1 N3 87.30(12) 3 4_565 ?
N5 Ni1 N3 173.85(13) . 4_565 ?
O5 Ni1 N3 92.13(12) . 4_565 ?
O3 Ni1 O1 166.76(11) 3 . ?
N5 Ni1 O1 91.27(12) . . ?
O5 Ni1 O1 97.87(11) . . ?
N3 Ni1 O1 91.86(12) 4_565 . ?
O3 Ni1 O2 105.08(11) 3 . ?
N5 Ni1 O2 88.78(12) . . ?
O5 Ni1 O2 159.53(11) . . ?
N3 Ni1 O2 88.05(12) 4_565 . ?
O1 Ni1 O2 61.67(10) . . ?
O3 Ni1 C1 135.82(12) 3 . ?
N5 Ni1 C1 90.04(13) . . ?
O5 Ni1 C1 128.80(12) . . ?
N3 Ni1 C1 89.92(12) 4_565 . ?
O1 Ni1 C1 30.94(11) . . ?
O2 Ni1 C1 30.73(11) . . ?
C1 O1 Ni1 89.5(2) . . ?
C1 O2 Ni1 88.0(2) . . ?
C20 O3 Ni1 127.2(3) . 3 ?
C11 N1 C13 106.7(3) . . ?
C11 N1 C14 126.3(3) . . ?
C13 N1 C14 126.7(3) . . ?
C11 N2 C12 105.7(3) . . ?
C10 N3 C9 106.0(3) . . ?
C10 N3 Ni1 132.0(3) . 4_566 ?
C9 N3 Ni1 121.9(3) . 4_566 ?
C10 N4 C8 107.5(3) . . ?
C10 N4 C5 128.9(3) . . ?
C8 N4 C5 123.5(3) . . ?
O2 C1 O1 120.8(3) . . ?
O2 C1 C2 119.8(3) . . ?
O1 C1 C2 119.3(3) . . ?
O2 C1 Ni1 61.30(19) . . ?
O1 C1 Ni1 59.52(19) . . ?
C2 C1 Ni1 177.4(3) . . ?
C3 C2 C7 119.6(4) . . ?
C3 C2 C1 121.0(4) . . ?
C7 C2 C1 119.4(4) . . ?
C2 C3 C4 120.7(4) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 118.8(4) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
Ni1 N5 H5A 109.5 . . ?
Ni1 N5 H5B 109.5 . . ?
H5A N5 H5B 109.5 . . ?
Ni1 N5 H5C 109.5 . . ?
H5A N5 H5C 109.5 . . ?
H5B N5 H5C 109.5 . . ?
C6 C5 C4 120.7(4) . . ?
C6 C5 N4 118.3(4) . . ?
C4 C5 N4 121.0(4) . . ?
Ni1 O5 H1 102(4) . . ?
Ni1 O5 H1B 99(4) . . ?
H1 O5 H1B 107(3) . . ?
C7 C6 C5 119.8(4) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C22 N7 C21 118.9(13) . . ?
C22 N7 C23 125.7(14) . . ?
C21 N7 C23 115.0(11) . . ?
C6 C7 C2 120.4(4) . . ?
C6 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?
C9 C8 N4 105.8(4) . . ?
C9 C8 H8 127.1 . . ?
N4 C8 H8 127.1 . . ?
C8 C9 N3 110.3(4) . . ?
C8 C9 H9 124.9 . . ?
N3 C9 H9 124.9 . . ?
N3 C10 N4 110.4(3) . . ?
N3 C10 C11 122.4(3) . . ?
N4 C10 C11 127.2(3) . . ?
N2 C11 N1 111.5(3) . . ?
N2 C11 C10 123.4(4) . . ?
N1 C11 C10 124.9(3) . . ?
N2 C12 C13 110.2(4) . . ?
N2 C12 H12 124.9 . . ?
C13 C12 H12 124.9 . . ?
C12 C13 N1 105.8(4) . . ?
C12 C13 H13 127.1 . . ?
N1 C13 H13 127.1 . . ?
C19 C14 C15 121.6(4) . . ?
C19 C14 N1 118.9(4) . . ?
C15 C14 N1 119.4(3) . . ?
C16 C15 C14 118.7(4) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
C15 C16 C17 121.0(4) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C18 C17 C16 119.1(4) . . ?
C18 C17 C20 120.7(4) . . ?
C16 C17 C20 120.1(4) . . ?
C17 C18 C19 120.3(4) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C14 C19 C18 119.4(4) . . ?
C14 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
O4 C20 O3 125.7(4) . . ?
O4 C20 C17 118.1(4) . . ?
O3 C20 C17 116.2(4) . . ?
O6 C21 N7 123.7(15) . . ?
O6 C21 H21 118.1 . . ?
N7 C21 H21 118.1 . . ?
N7 C22 H22A 109.5 . . ?
N7 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N7 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N7 C23 H23A 109.5 . . ?
N7 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N7 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
Ni1 O2 C1 O1 -0.1(4) . . . . ?
Ni1 O2 C1 C2 177.3(3) . . . . ?
Ni1 O1 C1 O2 0.1(4) . . . . ?
Ni1 O1 C1 C2 -177.3(3) . . . . ?
O2 C1 C2 C3 -175.4(4) . . . . ?
O1 C1 C2 C3 2.0(6) . . . . ?
O2 C1 C2 C7 4.6(6) . . . . ?
O1 C1 C2 C7 -178.1(4) . . . . ?
C7 C2 C3 C4 0.9(6) . . . . ?
C1 C2 C3 C4 -179.1(4) . . . . ?
C2 C3 C4 C5 0.7(7) . . . . ?
C3 C4 C5 C6 -2.3(7) . . . . ?
C3 C4 C5 N4 179.2(4) . . . . ?
C10 N4 C5 C6 137.0(4) . . . . ?
C8 N4 C5 C6 -38.7(6) . . . . ?
C10 N4 C5 C4 -44.5(6) . . . . ?
C8 N4 C5 C4 139.8(5) . . . . ?
C4 C5 C6 C7 2.3(7) . . . . ?
N4 C5 C6 C7 -179.1(4) . . . . ?
C5 C6 C7 C2 -0.7(7) . . . . ?
C3 C2 C7 C6 -0.9(6) . . . . ?
C1 C2 C7 C6 179.1(4) . . . . ?
C10 N4 C8 C9 0.9(5) . . . . ?
C5 N4 C8 C9 177.4(4) . . . . ?
N4 C8 C9 N3 -0.5(5) . . . . ?
C10 N3 C9 C8 -0.1(5) . . . . ?
Ni1 N3 C9 C8 -176.4(3) 4_566 . . . ?
C9 N3 C10 N4 0.7(5) . . . . ?
Ni1 N3 C10 N4 176.4(3) 4_566 . . . ?
C9 N3 C10 C11 -177.6(4) . . . . ?
Ni1 N3 C10 C11 -1.8(6) 4_566 . . . ?
C8 N4 C10 N3 -1.0(5) . . . . ?
C5 N4 C10 N3 -177.3(4) . . . . ?
C8 N4 C10 C11 177.2(4) . . . . ?
C5 N4 C10 C11 0.9(7) . . . . ?
C12 N2 C11 N1 -0.9(4) . . . . ?
C12 N2 C11 C10 174.3(4) . . . . ?
C13 N1 C11 N2 0.8(4) . . . . ?
C14 N1 C11 N2 -174.4(3) . . . . ?
C13 N1 C11 C10 -174.4(4) . . . . ?
C14 N1 C11 C10 10.4(6) . . . . ?
N3 C10 C11 N2 -54.8(6) . . . . ?
N4 C10 C11 N2 127.2(4) . . . . ?
N3 C10 C11 N1 119.8(4) . . . . ?
N4 C10 C11 N1 -58.1(6) . . . . ?
C11 N2 C12 C13 0.7(5) . . . . ?
N2 C12 C13 N1 -0.3(5) . . . . ?
C11 N1 C13 C12 -0.3(5) . . . . ?
C14 N1 C13 C12 174.9(4) . . . . ?
C11 N1 C14 C19 120.8(4) . . . . ?
C13 N1 C14 C19 -53.5(6) . . . . ?
C11 N1 C14 C15 -54.7(6) . . . . ?
C13 N1 C14 C15 131.0(5) . . . . ?
C19 C14 C15 C16 -2.4(7) . . . . ?
N1 C14 C15 C16 173.0(4) . . . . ?
C14 C15 C16 C17 -0.9(7) . . . . ?
C15 C16 C17 C18 3.1(7) . . . . ?
C15 C16 C17 C20 -172.7(4) . . . . ?
C16 C17 C18 C19 -2.2(6) . . . . ?
C20 C17 C18 C19 173.6(4) . . . . ?
C15 C14 C19 C18 3.3(7) . . . . ?
N1 C14 C19 C18 -172.1(4) . . . . ?
C17 C18 C19 C14 -0.9(7) . . . . ?
Ni1 O3 C20 O4 2.6(7) 3 . . . ?
Ni1 O3 C20 C17 -178.0(3) 3 . . . ?
C18 C17 C20 O4 171.0(5) . . . . ?
C16 C17 C20 O4 -13.3(7) . . . . ?
C18 C17 C20 O3 -8.4(6) . . . . ?
C16 C17 C20 O3 167.3(4) . . . . ?
C22 N7 C21 O6 179.2(14) . . . . ?
C23 N7 C21 O6 -7.1(19) . . . . ?

_refine_diff_density_max         1.668
_refine_diff_density_min         -0.738
_refine_diff_density_rms         0.112



####################################################################### 
# 
# 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 2174119'
loop_
_audit_author_name
_audit_author_address
'Yu Xinyu'
;Beijing Institute of Technolog
China
;
_audit_update_record             
;
2022-05-22 deposited with the CCDC.	2023-05-22 downloaded from the CCDC.
;
_audit_creation_date             2022-01-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H12 N4 O5 Zn, 0.5(C3 H7 N O)'
_chemical_formula_sum            'C21.50 H15.50 N4.50 O5.50 Zn'
_chemical_formula_weight         490.25
_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'
Zn Zn 0.2839 1.4301 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.8647(4)
_cell_length_b                   18.0466(10)
_cell_length_c                   18.6864(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.444(2)
_cell_angle_gamma                90
_cell_volume                     2295.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8246
_cell_measurement_temperature    298.01
_cell_measurement_theta_max      25.809
_cell_measurement_theta_min      2.257
_shelx_estimated_absorpt_T_max   0.851
_shelx_estimated_absorpt_T_min   0.808
_exptl_absorpt_coefficient_mu    1.112
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0939 before and 0.0554 after correction.
The Ratio of minimum to maximum transmission is 0.7715.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0665
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            37005
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.356
_diffrn_reflns_theta_min         2.471
_diffrn_ambient_temperature      298.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4108
_reflns_number_total             5722
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.191
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.123
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         5722
_refine_ls_number_restraints     75
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_gt           0.0561
_refine_ls_restrained_S_all      1.067
_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)+(0.0982P)²+3.5272P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1561
_refine_ls_wR_factor_ref         0.1783
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C5-O5
 1.22 with sigma of 0.02
 C5-N2
 1.36 with sigma of 0.02
 N2-C21
 1.45 with sigma of 0.02
 N2-C11
 1.46 with sigma of 0.02
 C5-C21
 2.46 with sigma of 0.04
 C5-C11
 2.45 with sigma of 0.04
 N2-C21 \\sim N2-C11
 with sigma of 0.02
3. Restrained planarity
 O5, N2, C5, C11, C21
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
O5 \\sim N2 \\sim C5 \\sim C11 \\sim C21: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
Uanis(O5) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C11) \\sim Ueq, Uanis(C21) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 O5, N2, C5, C11, C21
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: O5(0.5) N2(0.5) C5(0.5) H5(0.5) C11(0.5) H11A(0.5) H11B(0.5)
 H11C(0.5) C21(0.5) H21A(0.5) H21B(0.5) H21C(0.5)
7.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C9(H9), C13(H13), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20), C23(H23), C5(H5)
7.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C21(H21A,H21B,H21C)
;
_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
Zn1 Zn -0.00523(6) 0.59027(2) 0.43739(2) 0.02365(15) Uani 1 1 d . . . . .
O1 O 0.7944(4) 0.39461(15) 0.48070(14) 0.0304(6) Uani 1 1 d . . . . .
O2 O -0.1634(5) 0.4969(2) 0.3122(2) 0.0656(12) Uani 1 1 d . . . . .
O3 O -0.2728(5) 0.5590(2) 0.46084(18) 0.0473(8) Uani 1 1 d . . . . .
O4 O 0.1203(4) 0.51759(17) 0.38181(17) 0.0394(7) Uani 1 1 d . . . . .
O6 O 1.0299(4) 0.3337(2) 0.43456(16) 0.0431(8) Uani 1 1 d . . . . .
N1 N 0.5088(4) 0.19553(18) 0.10286(17) 0.0271(7) Uani 1 1 d . . . . .
N3 N 0.0922(5) 0.14955(19) 0.15587(19) 0.0331(8) Uani 1 1 d . . . . .
N4 N 0.4151(4) 0.29963(17) 0.15021(17) 0.0264(7) Uani 1 1 d . . . . .
N5 N 0.2753(4) 0.18236(18) 0.25781(17) 0.0265(6) Uani 1 1 d . . . . .
C1 C 0.4214(5) 0.2208(2) 0.3053(2) 0.0263(8) Uani 1 1 d . . . . .
C2 C 0.1117(6) 0.3445(2) 0.1900(2) 0.0318(9) Uani 1 1 d . . . . .
H2 H 0.040218 0.311390 0.158745 0.038 Uiso 1 1 calc R U . . .
C3 C 0.6182(6) 0.2532(2) 0.0806(2) 0.0346(9) Uani 1 1 d . . . . .
H3 H 0.713837 0.248776 0.049852 0.042 Uiso 1 1 calc R U . . .
C4 C 0.7014(5) 0.3041(2) 0.39093(19) 0.0268(8) Uani 1 1 d . . . . .
C6 C 0.6169(5) 0.2188(2) 0.2924(2) 0.0282(8) Uani 1 1 d . . . . .
H6 H 0.654447 0.189311 0.255677 0.034 Uiso 1 1 calc R U . . .
C7 C 0.0146(6) 0.4882(2) 0.3275(2) 0.0333(9) Uani 1 1 d . . . . .
C8 C 0.3877(5) 0.2250(2) 0.14428(19) 0.0237(7) Uani 1 1 d . . . . .
C9 C 0.0189(6) 0.3894(2) 0.2344(2) 0.0320(9) Uani 1 1 d . . . . .
H9 H -0.116774 0.386408 0.232966 0.038 Uiso 1 1 calc R U . . .
C10 C 0.2516(5) 0.1845(2) 0.1846(2) 0.0256(7) Uani 1 1 d . . . . .
C12 C 0.1228(6) 0.4391(2) 0.2811(2) 0.0266(8) Uani 1 1 d . . . . .
C13 C 0.5070(6) 0.3033(2) 0.4045(2) 0.0326(9) Uani 1 1 d . . . . .
H13 H 0.470551 0.330898 0.442678 0.039 Uiso 1 1 calc R U . . .
C14 C 0.8553(6) 0.3473(2) 0.43750(19) 0.0273(8) Uani 1 1 d . . . . .
C15 C 0.1171(6) 0.1437(2) 0.2768(2) 0.0341(9) Uani 1 1 d . . . . .
H15 H 0.089946 0.133763 0.323366 0.041 Uiso 1 1 calc R U . . .
C16 C 0.3245(6) 0.4435(2) 0.2824(2) 0.0306(8) Uani 1 1 d . . . . .
H16 H 0.396094 0.476578 0.313743 0.037 Uiso 1 1 calc R U . . .
C17 C 0.5651(6) 0.3173(2) 0.1102(2) 0.0350(9) Uani 1 1 d . . . . .
H17 H 0.618679 0.363956 0.104823 0.042 Uiso 1 1 calc R U . . .
C18 C 0.3672(6) 0.2619(2) 0.3619(2) 0.0316(9) Uani 1 1 d . . . . .
H18 H 0.237465 0.261717 0.371269 0.038 Uiso 1 1 calc R U . . .
C19 C 0.0098(6) 0.1233(2) 0.2148(2) 0.0369(10) Uani 1 1 d . . . . .
H19 H -0.104663 0.095318 0.211761 0.044 Uiso 1 1 calc R U . . .
C20 C 0.7532(5) 0.2609(2) 0.3347(2) 0.0293(8) Uani 1 1 d . . . . .
H20 H 0.883209 0.260580 0.325587 0.035 Uiso 1 1 calc R U . . .
C22 C 0.3139(5) 0.3495(2) 0.1928(2) 0.0256(7) Uani 1 1 d . . . . .
C23 C 0.4208(6) 0.3994(2) 0.2378(2) 0.0310(8) Uani 1 1 d . . . . .
H23 H 0.555965 0.403421 0.238079 0.037 Uiso 1 1 calc R U . . .
O5 O 0.279(2) 0.0887(8) 0.4651(8) 0.146(6) Uani 0.5 1 d D U P . .
N2 N 0.5739(13) 0.0752(4) 0.4379(3) 0.0422(17) Uani 0.5 1 d D U P . .
C5 C 0.3834(19) 0.0561(8) 0.4227(8) 0.095(4) Uani 0.5 1 d D U P . .
H5 H 0.334457 0.023504 0.386180 0.114 Uiso 0.5 1 calc R U P . .
C11 C 0.651(3) 0.1230(7) 0.4902(7) 0.109(5) Uani 0.5 1 d D U P . .
H11A H 0.547568 0.143130 0.514287 0.164 Uiso 0.5 1 calc R U P . .
H11B H 0.717373 0.162533 0.468880 0.164 Uiso 0.5 1 calc R U P . .
H11C H 0.742973 0.097163 0.524557 0.164 Uiso 0.5 1 calc R U P . .
C21 C 0.702(3) 0.0445(10) 0.3934(10) 0.122(6) Uani 0.5 1 d D U P . .
H21A H 0.756721 -0.000557 0.414589 0.183 Uiso 0.5 1 calc R U P . .
H21B H 0.805774 0.078987 0.388331 0.183 Uiso 0.5 1 calc R U P . .
H21C H 0.631000 0.034080 0.346784 0.183 Uiso 0.5 1 calc R U P . .


_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
Zn1 O1 1.985(3) 3_666 ?
Zn1 O3 2.023(3) . ?
Zn1 O4 1.943(3) . ?
Zn1 N1 2.042(3) 2 ?
O1 C14 1.281(4) . ?
O2 C7 1.229(5) . ?
O4 C7 1.284(5) . ?
O6 C14 1.231(5) . ?
N1 C3 1.380(5) . ?
N1 C8 1.319(5) . ?
N3 C10 1.316(5) . ?
N3 C19 1.384(6) . ?
N4 C8 1.362(5) . ?
N4 C17 1.385(5) . ?
N4 C22 1.438(5) . ?
N5 C1 1.430(5) . ?
N5 C10 1.358(5) . ?
N5 C15 1.375(5) . ?
C1 C6 1.395(5) . ?
C1 C18 1.380(5) . ?
C2 H2 0.9300 . ?
C2 C9 1.374(5) . ?
C2 C22 1.385(5) . ?
C3 H3 0.9300 . ?
C3 C17 1.352(6) . ?
C4 C13 1.390(5) . ?
C4 C14 1.498(5) . ?
C4 C20 1.390(5) . ?
C6 H6 0.9300 . ?
C6 C20 1.375(5) . ?
C7 C12 1.501(5) . ?
C8 C10 1.469(5) . ?
C9 H9 0.9300 . ?
C9 C12 1.382(6) . ?
C12 C16 1.384(5) . ?
C13 H13 0.9300 . ?
C13 C18 1.385(6) . ?
C15 H15 0.9300 . ?
C15 C19 1.342(6) . ?
C16 H16 0.9300 . ?
C16 C23 1.382(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C22 C23 1.378(5) . ?
C23 H23 0.9300 . ?
O5 C5 1.280(15) . ?
N2 C5 1.347(13) . ?
N2 C11 1.359(11) . ?
N2 C21 1.400(11) . ?
C5 H5 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

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 Zn1 O3 117.59(13) 3_666 . ?
O1 Zn1 N1 97.41(13) 3_666 2 ?
O3 Zn1 N1 111.82(13) . 2 ?
O4 Zn1 O1 100.10(12) . 3_666 ?
O4 Zn1 O3 113.91(14) . . ?
O4 Zn1 N1 114.59(13) . 2 ?
C14 O1 Zn1 108.2(2) . 3_666 ?
C7 O4 Zn1 117.2(3) . . ?
C3 N1 Zn1 124.9(2) . 2_545 ?
C8 N1 Zn1 127.8(3) . 2_545 ?
C8 N1 C3 106.3(3) . . ?
C10 N3 C19 104.1(3) . . ?
C8 N4 C17 106.7(3) . . ?
C8 N4 C22 126.3(3) . . ?
C17 N4 C22 126.9(3) . . ?
C10 N5 C1 126.5(3) . . ?
C10 N5 C15 106.2(3) . . ?
C15 N5 C1 126.8(3) . . ?
C6 C1 N5 119.5(3) . . ?
C18 C1 N5 119.9(3) . . ?
C18 C1 C6 120.5(3) . . ?
C9 C2 H2 120.7 . . ?
C9 C2 C22 118.7(4) . . ?
C22 C2 H2 120.7 . . ?
N1 C3 H3 125.2 . . ?
C17 C3 N1 109.6(3) . . ?
C17 C3 H3 125.2 . . ?
C13 C4 C14 121.4(3) . . ?
C20 C4 C13 118.5(3) . . ?
C20 C4 C14 120.0(3) . . ?
C1 C6 H6 120.5 . . ?
C20 C6 C1 118.9(3) . . ?
C20 C6 H6 120.5 . . ?
O2 C7 O4 125.1(4) . . ?
O2 C7 C12 119.5(4) . . ?
O4 C7 C12 115.4(4) . . ?
N1 C8 N4 110.8(3) . . ?
N1 C8 C10 126.2(3) . . ?
N4 C8 C10 122.8(3) . . ?
C2 C9 H9 119.3 . . ?
C2 C9 C12 121.5(4) . . ?
C12 C9 H9 119.3 . . ?
N3 C10 N5 112.5(3) . . ?
N3 C10 C8 125.5(3) . . ?
N5 C10 C8 122.0(3) . . ?
C9 C12 C7 119.6(3) . . ?
C9 C12 C16 118.8(3) . . ?
C16 C12 C7 121.6(4) . . ?
C4 C13 H13 119.7 . . ?
C18 C13 C4 120.7(3) . . ?
C18 C13 H13 119.7 . . ?
O1 C14 C4 116.7(3) . . ?
O6 C14 O1 124.0(4) . . ?
O6 C14 C4 119.2(3) . . ?
N5 C15 H15 126.9 . . ?
C19 C15 N5 106.2(4) . . ?
C19 C15 H15 126.9 . . ?
C12 C16 H16 119.6 . . ?
C23 C16 C12 120.8(4) . . ?
C23 C16 H16 119.6 . . ?
N4 C17 H17 126.8 . . ?
C3 C17 N4 106.5(3) . . ?
C3 C17 H17 126.8 . . ?
C1 C18 C13 119.7(3) . . ?
C1 C18 H18 120.2 . . ?
C13 C18 H18 120.2 . . ?
N3 C19 H19 124.5 . . ?
C15 C19 N3 111.0(3) . . ?
C15 C19 H19 124.5 . . ?
C4 C20 H20 119.2 . . ?
C6 C20 C4 121.6(3) . . ?
C6 C20 H20 119.2 . . ?
C2 C22 N4 119.5(3) . . ?
C23 C22 N4 119.3(3) . . ?
C23 C22 C2 121.1(3) . . ?
C16 C23 H23 120.4 . . ?
C22 C23 C16 119.2(4) . . ?
C22 C23 H23 120.4 . . ?
C5 N2 C11 126.3(13) . . ?
C5 N2 C21 116.1(13) . . ?
C11 N2 C21 117.6(15) . . ?
O5 C5 N2 111.1(14) . . ?
O5 C5 H5 124.5 . . ?
N2 C5 H5 124.5 . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C21 H21A 109.5 . . ?
N2 C21 H21B 109.5 . . ?
N2 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
Zn1 O1 C14 O6 -22.0(5) 3_666 . . . ?
Zn1 O1 C14 C4 154.9(3) 3_666 . . . ?
Zn1 O4 C7 O2 -7.5(6) . . . . ?
Zn1 O4 C7 C12 173.3(3) . . . . ?
Zn1 N1 C3 C17 171.0(3) 2_545 . . . ?
Zn1 N1 C8 N4 -169.7(2) 2_545 . . . ?
Zn1 N1 C8 C10 15.3(6) 2_545 . . . ?
O2 C7 C12 C9 -17.1(6) . . . . ?
O2 C7 C12 C16 161.1(4) . . . . ?
O4 C7 C12 C9 162.2(4) . . . . ?
O4 C7 C12 C16 -19.7(6) . . . . ?
N1 C3 C17 N4 -1.8(5) . . . . ?
N1 C8 C10 N3 -70.3(6) . . . . ?
N1 C8 C10 N5 112.8(4) . . . . ?
N4 C8 C10 N3 115.2(4) . . . . ?
N4 C8 C10 N5 -61.7(5) . . . . ?
N4 C22 C23 C16 -175.4(4) . . . . ?
N5 C1 C6 C20 174.6(4) . . . . ?
N5 C1 C18 C13 -175.4(4) . . . . ?
N5 C15 C19 N3 -1.6(5) . . . . ?
C1 N5 C10 N3 -173.3(3) . . . . ?
C1 N5 C10 C8 3.9(6) . . . . ?
C1 N5 C15 C19 174.0(4) . . . . ?
C1 C6 C20 C4 1.4(6) . . . . ?
C2 C9 C12 C7 178.7(4) . . . . ?
C2 C9 C12 C16 0.5(6) . . . . ?
C2 C22 C23 C16 2.1(6) . . . . ?
C3 N1 C8 N4 -0.4(4) . . . . ?
C3 N1 C8 C10 -175.5(4) . . . . ?
C4 C13 C18 C1 0.1(6) . . . . ?
C6 C1 C18 C13 2.2(6) . . . . ?
C7 C12 C16 C23 -178.0(4) . . . . ?
C8 N1 C3 C17 1.4(5) . . . . ?
C8 N4 C17 C3 1.5(5) . . . . ?
C8 N4 C22 C2 -46.2(6) . . . . ?
C8 N4 C22 C23 131.3(4) . . . . ?
C9 C2 C22 N4 176.0(4) . . . . ?
C9 C2 C22 C23 -1.4(6) . . . . ?
C9 C12 C16 C23 0.2(6) . . . . ?
C10 N3 C19 C15 1.2(5) . . . . ?
C10 N5 C1 C6 -47.2(6) . . . . ?
C10 N5 C1 C18 130.4(4) . . . . ?
C10 N5 C15 C19 1.3(4) . . . . ?
C12 C16 C23 C22 -1.4(6) . . . . ?
C13 C4 C14 O1 -13.5(6) . . . . ?
C13 C4 C14 O6 163.5(4) . . . . ?
C13 C4 C20 C6 0.8(6) . . . . ?
C14 C4 C13 C18 -178.7(4) . . . . ?
C14 C4 C20 C6 177.9(4) . . . . ?
C15 N5 C1 C6 141.6(4) . . . . ?
C15 N5 C1 C18 -40.8(6) . . . . ?
C15 N5 C10 N3 -0.7(4) . . . . ?
C15 N5 C10 C8 176.5(3) . . . . ?
C17 N4 C8 N1 -0.6(4) . . . . ?
C17 N4 C8 C10 174.6(4) . . . . ?
C17 N4 C22 C2 137.1(4) . . . . ?
C17 N4 C22 C23 -45.4(6) . . . . ?
C18 C1 C6 C20 -3.0(6) . . . . ?
C19 N3 C10 N5 -0.3(4) . . . . ?
C19 N3 C10 C8 -177.4(4) . . . . ?
C20 C4 C13 C18 -1.6(6) . . . . ?
C20 C4 C14 O1 169.5(4) . . . . ?
C20 C4 C14 O6 -13.5(6) . . . . ?
C22 N4 C8 N1 -177.9(3) . . . . ?
C22 N4 C8 C10 -2.6(6) . . . . ?
C22 N4 C17 C3 178.7(4) . . . . ?
C22 C2 C9 C12 0.1(7) . . . . ?
C11 N2 C5 O5 -0.6(16) . . . . ?
C21 N2 C5 O5 -178.2(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
