# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2248741'
loop_
_audit_author_name
_audit_author_address
'Francielli Sousa Santana'
;Universidade Federal do Parana
Brazil
;
_audit_update_record             
;
2023-03-14 deposited with the CCDC.	2023-08-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_structural     '[Cu(C4H5N3O2)2(NO3)2]'
_chemical_formula_moiety         'C8 H10 Cu N8 O10'
_chemical_formula_sum            'C8 H10 Cu N8 O10'
_chemical_formula_weight         441.78

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   7.3995(9)
_cell_length_b                   8.2828(12)
_cell_length_c                   12.5949(18)
_cell_angle_alpha                90
_cell_angle_beta                 94.276(5)
_cell_angle_gamma                90
_cell_volume                     769.77(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8191
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      27.54
_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            'dark blue'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.906
_exptl_crystal_F_000             446
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_min          0.074
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_max          0.129
_exptl_absorpt_coefficient_mu    1.497
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7097
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
SADABS-2012/1 - Bruker AXS area detector scaling and absorption correction 
;
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 Venture/Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            24278
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.946
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1773
_reflns_number_gt                1499
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3 (2015)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2015 (Sheldrick 2015a)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015b)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976 and Farrugia, 2012)'
_computing_publication_material  
'SHELXL-97 (Sheldrick, 2008) and WINGX (Farrugia, 2012)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0318P)²+0.3312P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1773
_refine_ls_number_parameters     144
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0239
_refine_ls_wR_factor_ref         0.0614
_refine_ls_wR_factor_gt          0.0587
_refine_ls_goodness_of_fit_ref   1.061
_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_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 0.000000 0.500000 0.500000 0.01767(9) Uani 1 2 d S . P . .
N1 N 0.15290(19) 0.14289(19) 0.47789(12) 0.0287(3) Uani 1 1 d . . . . .
N2 N 0.03552(18) 0.36899(17) 0.37240(11) 0.0213(3) Uani 1 1 d . . . . .
N3 N 0.0373(2) 0.2657(2) 0.21281(14) 0.0353(4) Uani 1 1 d . . . . .
N4 N 0.35911(19) 0.63282(17) 0.53652(11) 0.0226(3) Uani 1 1 d . . . . .
O2 O 0.2092(2) 0.00350(18) 0.47807(14) 0.0473(4) Uani 1 1 d . . . . .
O1 O 0.14351(18) 0.22544(18) 0.55860(10) 0.0340(3) Uani 1 1 d . . . . .
O1N4 O 0.22332(16) 0.61903(16) 0.46686(9) 0.0280(3) Uani 1 1 d . . . . .
O2N4 O 0.35508(19) 0.5704(2) 0.62410(11) 0.0399(4) Uani 1 1 d . . . . .
O3N4 O 0.49092(15) 0.71110(18) 0.51019(10) 0.0325(3) Uani 1 1 d . . . . .
C1 C -0.0692(3) 0.5516(3) 0.22212(18) 0.0390(5) Uani 1 1 d . . . . .
C2 C 0.0001(2) 0.3988(2) 0.26941(13) 0.0260(4) Uani 1 1 d . . . . .
C3 C 0.0959(2) 0.2133(2) 0.37819(14) 0.0246(4) Uani 1 1 d . . . . .
C4 C 0.0971(3) 0.1472(3) 0.27995(17) 0.0354(5) Uani 1 1 d . . . . .
H1A H -0.038(4) 0.646(4) 0.266(3) 0.088(11) Uiso 1 1 d D . . . .
H1B H -0.013(4) 0.572(4) 0.160(3) 0.086(10) Uiso 1 1 d D . . . .
H1C H -0.193(5) 0.550(4) 0.212(3) 0.086(11) Uiso 1 1 d . . . . .
H3N3 H 0.028(4) 0.259(3) 0.146(2) 0.061(8) Uiso 1 1 d . . . . .
H4 H 0.131(3) 0.046(3) 0.2593(19) 0.044(7) Uiso 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 N2 1.9729(14) . ?
Cu1 N2 1.9729(14) 3_566 ?
Cu1 O1N4 1.9949(12) 3_566 ?
Cu1 O1N4 1.9949(12) . ?
N1 O2 1.227(2) . ?
N1 O1 1.231(2) . ?
N1 C3 1.420(2) . ?
N2 C2 1.327(2) . ?
N2 C3 1.365(2) . ?
N3 C4 1.348(3) . ?
N3 C2 1.352(2) . ?
N3 H3N3 0.84(3) . ?
N4 O2N4 1.2205(19) . ?
N4 O3N4 1.2368(18) . ?
N4 O1N4 1.2888(18) . ?
C1 C2 1.475(3) . ?
C1 H1A 0.98(3) . ?
C1 H1B 0.92(4) . ?
C1 H1C 0.92(4) . ?
C3 C4 1.353(3) . ?
C4 H4 0.92(3) . ?

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
N2 Cu1 N2 180.00(7) . 3_566 ?
N2 Cu1 O1N4 93.52(5) . 3_566 ?
N2 Cu1 O1N4 86.48(5) 3_566 3_566 ?
N2 Cu1 O1N4 86.48(5) . . ?
N2 Cu1 O1N4 93.52(5) 3_566 . ?
O1N4 Cu1 O1N4 180.0 3_566 . ?
O2 N1 O1 124.12(17) . . ?
O2 N1 C3 117.79(16) . . ?
O1 N1 C3 118.09(15) . . ?
C2 N2 C3 105.54(15) . . ?
C2 N2 Cu1 131.70(13) . . ?
C3 N2 Cu1 122.62(12) . . ?
C4 N3 C2 109.44(16) . . ?
C4 N3 H3N3 125.1(19) . . ?
C2 N3 H3N3 125(2) . . ?
O2N4 N4 O3N4 122.50(14) . . ?
O2N4 N4 O1N4 120.49(14) . . ?
O3N4 N4 O1N4 117.02(14) . . ?
N4 O1N4 Cu1 121.15(10) . . ?
C2 C1 H1A 113.3(19) . . ?
C2 C1 H1B 110(2) . . ?
H1A C1 H1B 103(3) . . ?
C2 C1 H1C 111(2) . . ?
H1A C1 H1C 106(3) . . ?
H1B C1 H1C 113(3) . . ?
N2 C2 N3 109.31(17) . . ?
N2 C2 C1 126.28(18) . . ?
N3 C2 C1 124.41(18) . . ?
C4 C3 N2 110.95(17) . . ?
C4 C3 N1 128.37(18) . . ?
N2 C3 N1 120.64(15) . . ?
N3 C4 C3 104.77(18) . . ?
N3 C4 H4 124.7(15) . . ?
C3 C4 H4 130.5(15) . . ?

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
O2N4 N4 O1N4 Cu1 1.3(2) . . . . ?
O3N4 N4 O1N4 Cu1 -178.68(11) . . . . ?
C3 N2 C2 N3 0.01(19) . . . . ?
Cu1 N2 C2 N3 -175.70(12) . . . . ?
C3 N2 C2 C1 179.88(18) . . . . ?
Cu1 N2 C2 C1 4.2(3) . . . . ?
C4 N3 C2 N2 0.3(2) . . . . ?
C4 N3 C2 C1 -179.62(19) . . . . ?
C2 N2 C3 C4 -0.27(19) . . . . ?
Cu1 N2 C3 C4 175.93(13) . . . . ?
C2 N2 C3 N1 177.70(15) . . . . ?
Cu1 N2 C3 N1 -6.1(2) . . . . ?
O2 N1 C3 C4 -1.0(3) . . . . ?
O1 N1 C3 C4 178.70(18) . . . . ?
O2 N1 C3 N2 -178.59(16) . . . . ?
O1 N1 C3 N2 1.1(2) . . . . ?
C2 N3 C4 C3 -0.4(2) . . . . ?
N2 C3 C4 N3 0.4(2) . . . . ?
N1 C3 C4 N3 -177.36(17) . . . . ?

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
N3 H3N3 O3N4 0.84(3) 2.00(3) 2.837(2) 173(3) 2_545 yes

_refine_diff_density_max         0.276
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2248742'
loop_
_audit_author_name
_audit_author_address
'Francielli Sousa Santana'
;Universidade Federal do Parana
Brazil
;
_audit_update_record             
;
2023-03-14 deposited with the CCDC.	2023-08-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_structural     '[Cu(C4H5N3O2)2(H2O)2](NO3)2(H2O)2'
_chemical_formula_moiety         'C8 H14 Cu N6 O6, 2(N O3), 2(H2 O)'
_chemical_formula_sum            'C8 H18 Cu1 N8 O14'
_chemical_formula_weight         513.84


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      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                   6.714(2)
_cell_length_b                   10.504(4)
_cell_length_c                   14.095(5)
_cell_angle_alpha                90
_cell_angle_beta                 103.104(11)
_cell_angle_gamma                90
_cell_volume                     968.1(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    201(2)
_cell_measurement_reflns_used    8487
_cell_measurement_theta_min      3.67
_cell_measurement_theta_max      28.64
_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            'dark blue'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.763
_exptl_crystal_F_000             526
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_min          0.180
_exptl_crystal_size_mid          0.321
_exptl_crystal_size_max          0.356
_exptl_absorpt_coefficient_mu    1.218
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6783
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   
;
SADABS-2012/1 - Bruker AXS area detector scaling and absorption correction 
;
_diffrn_ambient_temperature      201(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 Venture/Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            46208
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.546
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2336
_reflns_number_gt                2080
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3 (2015)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2015 (Sheldrick 2015a)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015b)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976 and Farrugia, 2012)'
_computing_publication_material  
'SHELXL-97 (Sheldrick, 2008) and WINGX (Farrugia, 2012)'
_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)+(0.0400P)²+0.3056P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2336
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0242
_refine_ls_wR_factor_ref         0.0685
_refine_ls_wR_factor_gt          0.0668
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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
Cu Cu 0.500000 0.500000 0.500000 0.01933(9) Uani 1 2 d S . P . .
C1 C 0.1989(3) 0.74683(17) 0.37442(12) 0.0341(3) Uani 1 1 d . . . . .
C2 C 0.3006(2) 0.76013(13) 0.47869(10) 0.0225(3) Uani 1 1 d . . . . .
C3 C 0.4654(2) 0.72383(13) 0.62507(9) 0.0222(3) Uani 1 1 d . . . . .
C4 C 0.3994(2) 0.84615(14) 0.62531(11) 0.0278(3) Uani 1 1 d . . . . .
O1 O 0.63331(18) 0.54274(11) 0.68573(8) 0.0351(2) Uani 1 1 d . . . . .
O2 O 0.6224(2) 0.69969(15) 0.78472(8) 0.0505(3) Uani 1 1 d . . . . .
N1 N 0.58135(19) 0.65146(13) 0.70396(8) 0.0286(3) Uani 1 1 d . . . . .
N2 N 0.40538(16) 0.67016(10) 0.53447(8) 0.0205(2) Uani 1 1 d . . . . .
N3 N 0.29666(19) 0.86692(12) 0.53214(9) 0.0266(3) Uani 1 1 d . . . . .
O1W O 0.74104(19) 0.57915(12) 0.46988(10) 0.0366(3) Uani 1 1 d . . . . .
H1W1 H 0.758(4) 0.650(3) 0.4796(18) 0.059(7) Uiso 1 1 d . . . . .
H2W1 H 0.779(3) 0.551(2) 0.4206(17) 0.049(6) Uiso 1 1 d . . . . .
H1A H 0.066(4) 0.778(2) 0.3592(16) 0.054(6) Uiso 1 1 d . . . . .
H1B H 0.191(4) 0.666(3) 0.3542(19) 0.073(8) Uiso 1 1 d . . . . .
H1C H 0.272(4) 0.792(3) 0.340(2) 0.075(8) Uiso 1 1 d . . . . .
H1N3 H 0.246(3) 0.928(2) 0.5134(16) 0.045(6) Uiso 1 1 d . . . . .
H4 H 0.411(3) 0.9049(19) 0.6740(14) 0.038(5) Uiso 1 1 d . . . . .
N4 N 0.88111(18) 0.85301(11) 0.59385(9) 0.0248(2) Uani 1 1 d . . . . .
O1N4 O 0.93389(19) 0.76227(12) 0.64915(9) 0.0437(3) Uani 1 1 d . . . . .
O2N4 O 0.80673(19) 0.83773(12) 0.50500(8) 0.0400(3) Uani 1 1 d . . . . .
O3N4 O 0.8985(3) 0.96333(13) 0.62624(10) 0.0524(4) Uani 1 1 d . . . . .
O2W O 0.8602(2) 0.47894(14) 0.32003(11) 0.0428(3) Uani 1 1 d . . . . .
H1W2 H 0.888(5) 0.511(2) 0.272(2) 0.068(9) Uiso 1 1 d . . . . .
H2W2 H 0.932(4) 0.429(3) 0.334(2) 0.069(9) Uiso 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
Cu O1W 1.9499(12) . ?
Cu O1W 1.9499(12) 3_666 ?
Cu N2 1.9935(12) . ?
Cu N2 1.9935(12) 3_666 ?
C1 C2 1.480(2) . ?
C1 H1A 0.93(2) . ?
C1 H1B 0.90(3) . ?
C1 H1C 0.90(3) . ?
C2 N2 1.3249(17) . ?
C2 N3 1.3548(18) . ?
C3 C4 1.359(2) . ?
C3 N2 1.3702(17) . ?
C3 N1 1.4240(18) . ?
C4 N3 1.355(2) . ?
C4 H4 0.91(2) . ?
O1 N1 1.2380(18) . ?
O2 N1 1.2191(17) . ?
N3 H1N3 0.75(2) . ?
O1W H1W1 0.76(3) . ?
O1W H2W1 0.84(2) . ?
N4 O1N4 1.2313(17) . ?
N4 O3N4 1.2413(18) . ?
N4 O2N4 1.2489(16) . ?
O2W H1W2 0.82(3) . ?
O2W H2W2 0.71(3) . ?

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
O1W Cu O1W 180.0 . 3_666 ?
O1W Cu N2 89.82(5) . . ?
O1W Cu N2 90.18(5) 3_666 . ?
O1W Cu N2 90.18(5) . 3_666 ?
O1W Cu N2 89.82(5) 3_666 3_666 ?
N2 Cu N2 180.00(6) . 3_666 ?
C2 C1 H1A 113.5(14) . . ?
C2 C1 H1B 112.7(17) . . ?
H1A C1 H1B 106(2) . . ?
C2 C1 H1C 107.9(17) . . ?
H1A C1 H1C 107(2) . . ?
H1B C1 H1C 109(2) . . ?
N2 C2 N3 109.59(12) . . ?
N2 C2 C1 125.82(13) . . ?
N3 C2 C1 124.58(13) . . ?
C4 C3 N2 111.35(12) . . ?
C4 C3 N1 128.57(13) . . ?
N2 C3 N1 120.08(12) . . ?
N3 C4 C3 104.14(12) . . ?
N3 C4 H4 124.0(12) . . ?
C3 C4 H4 131.9(12) . . ?
O2 N1 O1 124.23(13) . . ?
O2 N1 C3 118.37(13) . . ?
O1 N1 C3 117.40(12) . . ?
C2 N2 C3 105.30(11) . . ?
C2 N2 Cu 130.58(9) . . ?
C3 N2 Cu 123.60(9) . . ?
C2 N3 C4 109.61(12) . . ?
C2 N3 H1N3 125.6(17) . . ?
C4 N3 H1N3 124.8(17) . . ?
Cu O1W H1W1 118.5(19) . . ?
Cu O1W H2W1 116.9(16) . . ?
H1W1 O1W H2W1 115(2) . . ?
O1N4 N4 O3N4 120.02(14) . . ?
O1N4 N4 O2N4 121.84(13) . . ?
O3N4 N4 O2N4 118.13(13) . . ?
H1W2 O2W H2W2 106(3) . . ?

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
N2 C3 C4 N3 -0.03(15) . . . . ?
N1 C3 C4 N3 -179.77(13) . . . . ?
C4 C3 N1 O2 3.8(2) . . . . ?
N2 C3 N1 O2 -175.95(13) . . . . ?
C4 C3 N1 O1 -176.51(14) . . . . ?
N2 C3 N1 O1 3.78(19) . . . . ?
N3 C2 N2 C3 0.57(15) . . . . ?
C1 C2 N2 C3 -178.27(14) . . . . ?
N3 C2 N2 Cu -171.26(9) . . . . ?
C1 C2 N2 Cu 9.9(2) . . . . ?
C4 C3 N2 C2 -0.33(15) . . . . ?
N1 C3 N2 C2 179.43(12) . . . . ?
C4 C3 N2 Cu 172.22(9) . . . . ?
N1 C3 N2 Cu -8.02(17) . . . . ?
N2 C2 N3 C4 -0.62(16) . . . . ?
C1 C2 N3 C4 178.23(14) . . . . ?
C3 C4 N3 C2 0.39(16) . . . . ?

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
O1W H1W1 O2N4 0.76(3) 2.02(3) 2.778(2) 179(3) . yes
O1W H2W1 O2W 0.84(2) 1.80(3) 2.6409(19) 175(2) . yes
C1 H1B O1 0.90(3) 2.61(3) 3.417(2) 151(2) 3_666 yes
C1 H1C O2 0.90(3) 2.64(3) 3.410(3) 144(2) 4_575 yes
N3 H1N3 O3N4 0.75(2) 2.29(2) 2.924(2) 143(2) 3_676 yes
C4 H4 O1 0.91(2) 2.52(2) 3.416(2) 166.2(16) 2_656 yes
O2W H1W2 O3N4 0.82(3) 2.09(3) 2.866(2) 159(3) 4_575 yes
O2W H2W2 O1N4 0.71(3) 2.19(3) 2.872(2) 161(3) 3_766 yes

_refine_diff_density_max         0.395
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.056

