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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1970186'
loop_
_audit_author_name
_audit_author_address
'Li Xiu-Yuan'
;Xi an Technological University
China
;
_audit_update_record             
;
2019-12-05 deposited with the CCDC.	2020-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H5 Cu N3 O4'
_chemical_formula_weight         294.71

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'

_space_group_crystal_system      tetragonal
_space_group_IT_number           134
_space_group_name_H-M_alt        'P 42/n n m'
_space_group_name_Hall           '-P 4ac 2bc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-y+1/2, x, z+1/2'
'y, -x+1/2, z+1/2'
'-x+1/2, y, -z+1/2'
'x, -y+1/2, -z+1/2'
'y, x, -z'
'-y+1/2, -x+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'y-1/2, -x, -z-1/2'
'-y, x-1/2, -z-1/2'
'x-1/2, -y, z-1/2'
'-x, y-1/2, z-1/2'
'-y, -x, z'
'y-1/2, x-1/2, z'

_cell_length_a                   20.0928(3)
_cell_length_b                   20.0928(3)
_cell_length_c                   8.0460(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3248.34(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2086
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      19.48

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_F_000             1176
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.351
_shelx_estimated_absorpt_T_min   0.833
_shelx_estimated_absorpt_T_max   0.877
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            93955
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.727
_diffrn_reflns_theta_max         25.355
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1558
_reflns_number_gt                1427
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0436P)²+7.5421P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1558
_refine_ls_number_parameters     124
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.1027
_refine_ls_wR_factor_gt          0.0998
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.120
_refine_ls_shift/su_max          0.003
_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 0.52393(2) 1.02393(2) 0.14381(6) 0.02114(18) Uani 1 2 d S T P . .
N1 N 0.3508(2) 0.9566(3) 0.4431(6) 0.0318(11) Uani 0.5 1 d . . P . .
N2 N 0.3643(5) 0.8914(4) 0.4497(11) 0.110(4) Uani 0.5 1 d . U P . .
N3 N 0.4269(3) 0.9465(3) 0.6356(6) 0.033(2) Uani 0.5 1 d . . P . .
O1 O 0.43000(10) 1.02674(11) 0.2083(3) 0.0391(6) Uani 1 1 d . . . . .
O2 O 0.38960(10) 0.98628(11) -0.0318(3) 0.0392(6) Uani 1 1 d . . . . .
C1 C 0.38407(15) 1.00655(15) 0.1156(4) 0.0330(7) Uani 1 1 d . . . . .
C2 C 0.31472(15) 1.00669(17) 0.1868(4) 0.0361(7) Uani 1 1 d . . . . .
C3 C 0.3000(3) 0.9838(4) 0.3388(8) 0.0306(13) Uani 0.5 1 d . . P . .
C4 C 0.2351(3) 0.9827(4) 0.4012(9) 0.0341(15) Uani 0.5 1 d . . P . .
H4 H 0.2266 0.9629 0.5078 0.041 Uiso 0.5 1 d R U P . .
C5 C 0.2600(3) 1.0297(5) 0.0854(10) 0.057(2) Uani 0.5 1 d . . P . .
H5 H 0.2681 1.0436 -0.0269 0.068 Uiso 0.5 1 d R U P . .
C6 C 0.1959(3) 1.0313(4) 0.1491(9) 0.0468(19) Uani 0.5 1 d . . P . .
H6 H 0.1598 1.0487 0.0842 0.056 Uiso 0.5 1 d R U P . .
C7 C 0.4104(5) 0.8897(5) 0.5722(13) 0.094(4) Uani 0.5 1 d . U P . .
H7 H 0.4263 0.8484 0.6172 0.112 Uiso 0.5 1 d R U P . .
C8 C 0.3876(4) 0.9879(3) 0.5540(11) 0.057(2) Uani 0.5 1 d . . P . .
H8 H 0.3850 1.0348 0.5753 0.069 Uiso 0.5 1 d 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
Cu1 O1 1.958(2) . ?
Cu1 O1 1.958(2) 16_565 ?
Cu1 O2 1.968(2) 8_665 ?
Cu1 O2 1.968(2) 9_675 ?
Cu1 N3 2.117(5) 8_666 ?
Cu1 N3 2.117(5) 9_676 ?
Cu1 Cu1 2.6843(10) 9_675 ?
N1 C8 1.319(9) . ?
N1 N2 1.339(9) . ?
N1 C3 1.430(8) . ?
N1 C7 1.597(11) 16_565 ?
N1 C6 1.920(10) 5 ?
N2 N2 0.769(16) 16_565 ?
N2 C7 1.174(11) 16_565 ?
N2 C7 1.353(11) . ?
N3 N3 0.557(13) 16_565 ?
N3 C7 1.159(11) 16_565 ?
N3 C7 1.292(10) . ?
N3 C8 1.322(10) . ?
N3 C8 1.826(9) 16_565 ?
N3 Cu1 2.117(5) 9_676 ?
O1 C1 1.254(4) . ?
O2 C1 1.259(4) . ?
O2 Cu1 1.968(2) 9_675 ?
C1 C2 1.506(4) . ?
C2 C4 1.318(8) 5 ?
C2 C3 1.340(7) . ?
C2 C6 1.427(8) 5 ?
C2 C5 1.444(8) . ?
C3 C6 0.964(9) 5 ?
C3 C4 1.397(9) . ?
C3 C5 1.637(10) 5 ?
C4 C5 0.957(9) 5 ?
C4 C2 1.318(7) 5 ?
C4 C6 1.743(10) 5 ?
C4 H4 0.9600 . ?
C5 C4 0.957(9) 5 ?
C5 C6 1.387(10) . ?
C5 C3 1.637(10) 5 ?
C5 H5 0.9601 . ?
C6 C3 0.964(9) 5 ?
C6 C2 1.427(8) 5 ?
C6 C4 1.744(10) 5 ?
C6 N1 1.920(10) 5 ?
C6 H6 0.9600 . ?
C7 C7 0.589(16) 16_565 ?
C7 N3 1.159(10) 16_565 ?
C7 N2 1.174(11) 16_565 ?
C7 C8 1.564(12) 16_565 ?
C7 N1 1.597(11) 16_565 ?
C7 C8 2.031(11) . ?
C7 H7 0.9601 . ?
C8 C7 1.564(12) 16_565 ?
C8 N3 1.826(9) 16_565 ?
C8 H8 0.9599 . ?

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 89.16(13) . 16_565 ?
O1 Cu1 O2 89.73(10) . 8_665 ?
O1 Cu1 O2 167.21(10) 16_565 8_665 ?
O1 Cu1 O2 167.21(10) . 9_675 ?
O1 Cu1 O2 89.73(10) 16_565 9_675 ?
O2 Cu1 O2 88.53(13) 8_665 9_675 ?
O1 Cu1 N3 92.01(17) . 8_666 ?
O1 Cu1 N3 102.70(17) 16_565 8_666 ?
O2 Cu1 N3 90.07(17) 8_665 8_666 ?
O2 Cu1 N3 100.66(17) 9_675 8_666 ?
O1 Cu1 N3 102.69(17) . 9_676 ?
O1 Cu1 N3 92.01(17) 16_565 9_676 ?
O2 Cu1 N3 100.66(16) 8_665 9_676 ?
O2 Cu1 N3 90.07(17) 9_675 9_676 ?
N3 Cu1 N3 15.1(3) 8_666 9_676 ?
O1 Cu1 Cu1 83.87(7) . 9_675 ?
O1 Cu1 Cu1 83.87(7) 16_565 9_675 ?
O2 Cu1 Cu1 83.34(7) 8_665 9_675 ?
O2 Cu1 Cu1 83.34(7) 9_675 9_675 ?
N3 Cu1 Cu1 172.24(17) 8_666 9_675 ?
N3 Cu1 Cu1 172.24(17) 9_676 9_675 ?
C8 N1 N2 109.0(6) . . ?
C8 N1 C3 128.0(6) . . ?
N2 N1 C3 122.8(6) . . ?
C8 N1 C7 64.0(5) . 16_565 ?
N2 N1 C7 46.1(5) . 16_565 ?
C3 N1 C7 162.4(6) . 16_565 ?
C8 N1 C6 99.3(5) . 5 ?
N2 N1 C6 151.7(5) . 5 ?
C3 N1 C6 29.0(3) . 5 ?
C7 N1 C6 160.9(5) 16_565 5 ?
N2 N2 C7 85.6(6) 16_565 16_565 ?
N2 N2 N1 146.7(5) 16_565 . ?
C7 N2 N1 78.6(7) 16_565 . ?
N2 N2 C7 59.9(5) 16_565 . ?
C7 N2 C7 25.7(7) 16_565 . ?
N1 N2 C7 101.1(7) . . ?
N3 N3 C7 90.8(5) 16_565 16_565 ?
N3 N3 C7 63.7(4) 16_565 . ?
C7 N3 C7 27.1(7) 16_565 . ?
N3 N3 C8 150.2(5) 16_565 . ?
C7 N3 C8 77.8(6) 16_565 . ?
C7 N3 C8 101.9(6) . . ?
N3 N3 C8 21.1(3) 16_565 16_565 ?
C7 N3 C8 82.5(6) 16_565 16_565 ?
C7 N3 C8 57.2(5) . 16_565 ?
C8 N3 C8 129.1(8) . 16_565 ?
N3 N3 Cu1 82.44(17) 16_565 9_676 ?
C7 N3 Cu1 147.7(7) 16_565 9_676 ?
C7 N3 Cu1 134.3(5) . 9_676 ?
C8 N3 Cu1 121.3(5) . 9_676 ?
C8 N3 Cu1 99.8(4) 16_565 9_676 ?
C1 O1 Cu1 122.9(2) . . ?
C1 O2 Cu1 122.9(2) . 9_675 ?
O1 C1 O2 126.9(3) . . ?
O1 C1 C2 117.0(3) . . ?
O2 C1 C2 116.1(3) . . ?
C4 C2 C3 101.3(5) 5 . ?
C4 C2 C6 120.7(4) 5 5 ?
C3 C2 C6 40.6(4) . 5 ?
C4 C2 C5 40.2(4) 5 . ?
C3 C2 C5 117.2(4) . . ?
C6 C2 C5 107.3(5) 5 . ?
C4 C2 C1 119.9(4) 5 . ?
C3 C2 C1 123.4(4) . . ?
C6 C2 C1 119.4(4) 5 . ?
C5 C2 C1 119.3(4) . . ?
C6 C3 C2 74.5(6) 5 . ?
C6 C3 C4 93.4(7) 5 . ?
C2 C3 C4 122.7(5) . . ?
C6 C3 N1 105.0(8) 5 . ?
C2 C3 N1 120.6(5) . . ?
C4 C3 N1 116.7(5) . . ?
C6 C3 C5 57.7(6) 5 5 ?
C2 C3 C5 108.0(6) . 5 ?
C4 C3 C5 35.7(4) . 5 ?
N1 C3 C5 121.5(6) . 5 ?
C5 C4 C2 77.0(7) 5 5 ?
C5 C4 C3 86.0(7) 5 . ?
C2 C4 C3 120.6(5) 5 . ?
C5 C4 C6 52.5(6) 5 5 ?
C2 C4 C6 105.9(5) 5 5 ?
C3 C4 C6 33.5(4) . 5 ?
C5 C4 H4 109.1 5 . ?
C2 C4 H4 119.8 5 . ?
C3 C4 H4 119.6 . . ?
C6 C4 H4 125.5 5 . ?
C4 C5 C6 94.3(8) 5 . ?
C4 C5 C2 62.8(6) 5 . ?
C6 C5 C2 120.4(6) . . ?
C4 C5 C3 58.3(6) 5 5 ?
C6 C5 C3 36.0(4) . 5 ?
C2 C5 C3 99.7(6) . 5 ?
C4 C5 H5 112.1 5 . ?
C6 C5 H5 119.9 . . ?
C2 C5 H5 119.8 . . ?
C3 C5 H5 129.8 5 . ?
C3 C6 C5 86.3(8) 5 . ?
C3 C6 C2 64.9(6) 5 5 ?
C5 C6 C2 118.2(6) . 5 ?
C3 C6 C4 53.1(6) 5 5 ?
C5 C6 C4 33.2(4) . 5 ?
C2 C6 C4 98.0(5) 5 5 ?
C3 C6 N1 46.0(6) 5 5 ?
C5 C6 N1 107.1(7) . 5 ?
C2 C6 N1 90.7(5) 5 5 ?
C4 C6 N1 81.9(5) 5 5 ?
C3 C6 H6 118.7 5 . ?
C5 C6 H6 120.7 . . ?
C2 C6 H6 121.1 5 . ?
C4 C6 H6 132.7 5 . ?
N1 C6 H6 72.8 5 . ?
C7 C7 N3 89.2(5) 16_565 16_565 ?
C7 C7 N2 94.4(6) 16_565 16_565 ?
N3 C7 N2 148.6(13) 16_565 16_565 ?
C7 C7 N3 63.7(4) 16_565 . ?
N3 C7 N3 25.5(6) 16_565 . ?
N2 C7 N3 143.0(11) 16_565 . ?
C7 C7 N2 59.9(5) 16_565 . ?
N3 C7 N2 137.2(10) 16_565 . ?
N2 C7 N2 34.5(8) 16_565 . ?
N3 C7 N2 116.2(7) . . ?
C7 C7 C8 136.3(5) 16_565 16_565 ?
N3 C7 C8 55.7(6) 16_565 16_565 ?
N2 C7 C8 103.6(9) 16_565 16_565 ?
N3 C7 C8 78.9(7) . 16_565 ?
N2 C7 C8 127.9(10) . 16_565 ?
C7 C7 N1 139.2(4) 16_565 16_565 ?
N3 C7 N1 103.9(9) 16_565 16_565 ?
N2 C7 N1 55.3(6) 16_565 16_565 ?
N3 C7 N1 122.8(9) . 16_565 ?
N2 C7 N1 86.3(6) . 16_565 ?
C8 C7 N1 49.3(5) 16_565 16_565 ?
C7 C7 C8 32.1(4) 16_565 . ?
N3 C7 C8 63.1(5) 16_565 . ?
N2 C7 C8 106.8(8) 16_565 . ?
N3 C7 C8 39.6(4) . . ?
N2 C7 C8 76.6(5) . . ?
C8 C7 C8 104.2(8) 16_565 . ?
N1 C7 C8 124.1(8) 16_565 . ?
C7 C7 H7 147.7 16_565 . ?
N3 C7 H7 100.6 16_565 . ?
N2 C7 H7 92.8 16_565 . ?
N3 C7 H7 122.0 . . ?
N2 C7 H7 121.5 . . ?
C8 C7 H7 71.5 16_565 . ?
N1 C7 H7 68.3 16_565 . ?
C8 C7 H7 160.4 . . ?
N1 C8 N3 111.8(6) . . ?
N1 C8 C7 66.7(5) . 16_565 ?
N3 C8 C7 46.4(4) . 16_565 ?
N1 C8 N3 106.7(5) . 16_565 ?
N3 C8 N3 8.7(3) . 16_565 ?
C7 C8 N3 44.0(4) 16_565 16_565 ?
N1 C8 C7 73.3(5) . . ?
N3 C8 C7 38.5(4) . . ?
C7 C8 C7 11.6(3) 16_565 . ?
N3 C8 C7 34.5(3) 16_565 . ?
N1 C8 H8 124.0 . . ?
N3 C8 H8 124.2 . . ?
C7 C8 H8 164.3 16_565 . ?
N3 C8 H8 129.0 16_565 . ?
C7 C8 H8 162.5 . . ?

_refine_diff_density_max         0.494
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.068



