# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_PA86_A
_database_code_depnum_ccdc_archive 'CCDC 2234588'
loop_
_audit_author_name
_audit_author_address
'Atash Gurbanov'
;Instituto Superior Tecnico
Portugal
;
_audit_update_record             
;
2023-01-05 deposited with the CCDC.	2023-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H24 Cu2 N8 O8'
_chemical_formula_sum            'C24 H24 Cu2 N8 O8'
_chemical_formula_weight         679.59

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3312(17)
_cell_length_b                   9.3618(19)
_cell_length_c                   9.4050(15)
_cell_angle_alpha                60.556(6)
_cell_angle_beta                 76.213(6)
_cell_angle_gamma                68.001(7)
_cell_volume                     661.9(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6770
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      26.50

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_F_000             346
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.672
_shelx_estimated_absorpt_T_min   0.680
_shelx_estimated_absorpt_T_max   0.731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.654
_exptl_absorpt_correction_T_max  0.703
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_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 D8 Quest PHOTON 100 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14352
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.874
_diffrn_reflns_theta_max         26.571
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2728
_reflns_number_gt                2446
_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'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0239P)²+0.5617P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2728
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_ref         0.0698
_refine_ls_wR_factor_gt          0.0675
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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 0.11828(3) 0.57885(3) 0.51324(3) 0.01451(9) Uani 1 1 d . . . . .
O1 O -0.0105(2) 0.3973(2) 0.89092(19) 0.0255(4) Uani 1 1 d . . . . .
O2 O -0.01938(17) 0.41393(19) 0.64972(17) 0.0165(3) Uani 1 1 d . . . . .
O3 O 0.41143(18) 0.5105(2) 0.82579(18) 0.0207(3) Uani 1 1 d . . . . .
O4 O -0.07974(18) 0.7993(2) 0.54286(18) 0.0192(3) Uani 1 1 d . . . . .
H4O H -0.165227 0.779834 0.556740 0.029 Uiso 1 1 d R U . . .
N1 N 0.2270(2) 0.5114(2) 0.6958(2) 0.0183(4) Uani 1 1 d . . . . .
H1N H 0.177694 0.452986 0.789586 0.022 Uiso 1 1 d R U . . .
N2 N 0.3700(2) 0.7335(2) 0.3927(2) 0.0163(4) Uani 1 1 d . . . . .
N3 N 0.2566(2) 0.7098(2) 0.3557(2) 0.0148(3) Uani 1 1 d . . . . .
N4 N 0.6412(3) 0.7401(3) 0.5628(3) 0.0314(5) Uani 1 1 d . . . . .
C1 C 0.3414(2) 0.5559(3) 0.6951(3) 0.0159(4) Uani 1 1 d . . . . .
C2 C 0.4089(2) 0.6660(3) 0.5440(3) 0.0175(4) Uani 1 1 d . . . . .
C3 C 0.5385(3) 0.7081(3) 0.5541(3) 0.0211(5) Uani 1 1 d . . . . .
C4 C 0.2392(2) 0.8008(3) 0.1833(2) 0.0147(4) Uani 1 1 d . . . . .
C5 C 0.3108(3) 0.9296(3) 0.0831(3) 0.0192(4) Uani 1 1 d . . . . .
H5 H 0.365349 0.959857 0.132255 0.023 Uiso 1 1 calc R U . . .
C6 C 0.3039(3) 1.0135(3) -0.0852(3) 0.0231(5) Uani 1 1 d . . . . .
H6 H 0.353398 1.100106 -0.150041 0.028 Uiso 1 1 calc R U . . .
C7 C -0.2250(3) 0.0289(3) 1.1590(3) 0.0256(5) Uani 1 1 d . . . . .
H7 H -0.222328 -0.025465 1.274649 0.031 Uiso 1 1 calc R U . . .
C8 C -0.1502(3) 0.1512(3) 1.0617(3) 0.0221(5) Uani 1 1 d . . . . .
H8 H -0.094814 0.178868 1.112586 0.027 Uiso 1 1 calc R U . . .
C9 C -0.1526(2) 0.2365(3) 0.8904(3) 0.0165(4) Uani 1 1 d . . . . .
C10 C -0.0571(2) 0.3577(3) 0.8075(2) 0.0163(4) Uani 1 1 d . . . . .
C11 C 0.3562(3) 0.3969(3) 0.9842(3) 0.0242(5) Uani 1 1 d . . . . .
H11A H 0.416280 0.374267 1.069401 0.036 Uiso 1 1 calc R U . . .
H11B H 0.368454 0.288046 0.984525 0.036 Uiso 1 1 calc R U . . .
H11C H 0.246508 0.451469 1.005589 0.036 Uiso 1 1 calc R U . . .
C12 C -0.0885(3) 0.8456(3) 0.6687(3) 0.0309(6) Uani 1 1 d . . . . .
H12A H -0.191038 0.926278 0.673957 0.046 Uiso 1 1 calc R U . . .
H12B H -0.008766 0.900413 0.644776 0.046 Uiso 1 1 calc R U . . .
H12C H -0.071869 0.742133 0.773928 0.046 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 N1 1.9133(18) . ?
Cu1 O2 1.9316(14) 2_566 ?
Cu1 N3 1.9622(17) . ?
Cu1 O2 2.1055(14) . ?
Cu1 O4 2.2834(16) . ?
O1 C10 1.229(3) . ?
O2 C10 1.313(3) . ?
O3 C1 1.334(2) . ?
O3 C11 1.450(3) . ?
O4 C12 1.424(3) . ?
O4 H4O 0.8500 . ?
N1 C1 1.281(3) . ?
N1 H1N 0.9000 . ?
N2 N3 1.311(2) . ?
N2 C2 1.322(3) . ?
N3 C4 1.430(3) . ?
N4 C3 1.136(3) . ?
C1 C2 1.448(3) . ?
C2 C3 1.441(3) . ?
C4 C9 1.404(3) 2_566 ?
C4 C5 1.405(3) . ?
C5 C6 1.384(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.384(3) 2_566 ?
C6 H6 0.9500 . ?
C7 C8 1.378(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.405(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.498(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

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
N1 Cu1 O2 165.75(7) . 2_566 ?
N1 Cu1 N3 92.80(7) . . ?
O2 Cu1 N3 95.25(7) 2_566 . ?
N1 Cu1 O2 94.62(7) . . ?
O2 Cu1 O2 75.65(6) 2_566 . ?
N3 Cu1 O2 168.02(6) . . ?
N1 Cu1 O4 96.73(7) . . ?
O2 Cu1 O4 93.57(6) 2_566 . ?
N3 Cu1 O4 99.18(7) . . ?
O2 Cu1 O4 89.28(6) . . ?
C10 O2 Cu1 128.06(13) . 2_566 ?
C10 O2 Cu1 125.51(12) . . ?
Cu1 O2 Cu1 104.35(6) 2_566 . ?
C1 O3 C11 117.54(16) . . ?
C12 O4 Cu1 122.49(14) . . ?
C12 O4 H4O 103.8 . . ?
Cu1 O4 H4O 109.3 . . ?
C1 N1 Cu1 127.85(16) . . ?
C1 N1 H1N 121.8 . . ?
Cu1 N1 H1N 109.8 . . ?
N3 N2 C2 123.44(17) . . ?
N2 N3 C4 111.11(16) . . ?
N2 N3 Cu1 125.61(14) . . ?
C4 N3 Cu1 123.20(13) . . ?
N1 C1 O3 126.20(19) . . ?
N1 C1 C2 121.35(19) . . ?
O3 C1 C2 112.45(17) . . ?
N2 C2 C3 113.43(19) . . ?
N2 C2 C1 128.83(19) . . ?
C3 C2 C1 117.73(19) . . ?
N4 C3 C2 179.5(3) . . ?
C9 C4 C5 118.41(19) 2_566 . ?
C9 C4 N3 121.43(18) 2_566 . ?
C5 C4 N3 120.15(18) . . ?
C6 C5 C4 121.8(2) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C7 C6 C5 119.9(2) 2_566 . ?
C7 C6 H6 120.0 2_566 . ?
C5 C6 H6 120.0 . . ?
C8 C7 C6 118.9(2) . 2_566 ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 2_566 . ?
C7 C8 C9 122.6(2) . . ?
C7 C8 H8 118.7 . . ?
C9 C8 H8 118.7 . . ?
C4 C9 C8 118.29(19) 2_566 . ?
C4 C9 C10 127.67(19) 2_566 . ?
C8 C9 C10 114.03(18) . . ?
O1 C10 O2 121.22(19) . . ?
O1 C10 C9 118.74(19) . . ?
O2 C10 C9 119.98(17) . . ?
O3 C11 H11A 109.5 . . ?
O3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
C2 N2 N3 C4 178.90(19) . . . . ?
C2 N2 N3 Cu1 2.2(3) . . . . ?
Cu1 N1 C1 O3 177.71(16) . . . . ?
Cu1 N1 C1 C2 -2.1(3) . . . . ?
C11 O3 C1 N1 1.5(3) . . . . ?
C11 O3 C1 C2 -178.63(19) . . . . ?
N3 N2 C2 C3 179.22(19) . . . . ?
N3 N2 C2 C1 0.6(4) . . . . ?
N1 C1 C2 N2 -0.7(4) . . . . ?
O3 C1 C2 N2 179.5(2) . . . . ?
N1 C1 C2 C3 -179.3(2) . . . . ?
O3 C1 C2 C3 0.9(3) . . . . ?
N2 N3 C4 C9 164.42(19) . . . 2_566 ?
Cu1 N3 C4 C9 -18.8(3) . . . 2_566 ?
N2 N3 C4 C5 -15.0(3) . . . . ?
Cu1 N3 C4 C5 161.81(16) . . . . ?
C9 C4 C5 C6 -3.1(3) 2_566 . . . ?
N3 C4 C5 C6 176.3(2) . . . . ?
C4 C5 C6 C7 0.0(4) . . . 2_566 ?
C6 C7 C8 C9 0.9(4) 2_566 . . . ?
C7 C8 C9 C4 2.2(4) . . . 2_566 ?
C7 C8 C9 C10 -176.9(2) . . . . ?
Cu1 O2 C10 O1 -162.12(16) 2_566 . . . ?
Cu1 O2 C10 O1 -1.2(3) . . . . ?
Cu1 O2 C10 C9 20.7(3) 2_566 . . . ?
Cu1 O2 C10 C9 -178.30(14) . . . . ?
C4 C9 C10 O1 167.6(2) 2_566 . . . ?
C8 C9 C10 O1 -13.3(3) . . . . ?
C4 C9 C10 O2 -15.2(3) 2_566 . . . ?
C8 C9 C10 O2 163.9(2) . . . . ?

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
O4 H4O N4 0.85 1.96 2.805(2) 173.5 1_455 yes
N1 H1N O1 0.90 1.91 2.707(2) 146.0 . yes

_refine_diff_density_max         0.361
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.068

####################################################################### 
# 
# 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_M2_A
_database_code_depnum_ccdc_archive 'CCDC 2234591'
loop_
_audit_author_name
_audit_author_address
'Atash Gurbanov'
;Instituto Superior Tecnico
Portugal
;
_audit_update_record             
;
2023-01-05 deposited with the CCDC.	2023-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H18 Cu N6 O4, H2 O'
_chemical_formula_sum            'C21 H20 Cu N6 O5'
_chemical_formula_weight         499.97

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6551(13)
_cell_length_b                   10.2932(18)
_cell_length_c                   12.572(2)
_cell_angle_alpha                71.796(6)
_cell_angle_beta                 79.500(6)
_cell_angle_gamma                82.626(6)
_cell_volume                     1043.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4171
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      26.37

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_F_000             514
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    1.096
_shelx_estimated_absorpt_T_min   0.771
_shelx_estimated_absorpt_T_max   0.871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.754
_exptl_absorpt_correction_T_max  0.858
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_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 D8 Quest PHOTON 100 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23523
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_av_R_equivalents  0.0837
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.281
_diffrn_reflns_theta_max         26.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4283
_reflns_number_gt                3498
_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'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0304P)²+1.0545P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4283
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.0871
_refine_ls_wR_factor_gt          0.0810
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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 0.64216(4) 0.33058(3) 0.44082(3) 0.01522(10) Uani 1 1 d . . . . .
O1 O 0.7300(2) 0.46617(19) 0.48454(15) 0.0197(4) Uani 1 1 d . . . . .
O2 O 0.8270(2) 0.6677(2) 0.44555(16) 0.0219(4) Uani 1 1 d . . . . .
O3 O 0.3267(2) 0.2406(2) 0.26291(16) 0.0200(4) Uani 1 1 d . . . . .
O4 O 0.8213(2) 0.1364(2) 0.47077(17) 0.0265(5) Uani 1 1 d . . . . .
H4A H 0.847022 0.077819 0.434438 0.040 Uiso 1 1 d R U . . .
H4B H 0.879571 0.111749 0.522328 0.040 Uiso 1 1 d R U . . .
O5 O 0.9552(2) 0.9193(2) 0.37648(16) 0.0250(5) Uani 1 1 d . . . . .
H5A H 0.990984 0.944684 0.306143 0.038 Uiso 1 1 d R U . . .
H5B H 0.903424 0.852644 0.380623 0.038 Uiso 1 1 d R U . . .
N1 N 0.4595(3) 0.2835(2) 0.39352(19) 0.0201(5) Uani 1 1 d . . . . .
H1N H 0.370439 0.275574 0.440027 0.024 Uiso 1 1 d R U . . .
N2 N 0.7016(3) 0.3815(2) 0.19355(18) 0.0157(5) Uani 1 1 d . . . . .
N3 N 0.7437(3) 0.3981(2) 0.28230(18) 0.0154(5) Uani 1 1 d . . . . .
N4 N 0.5128(3) 0.3210(3) 0.0047(2) 0.0297(6) Uani 1 1 d . . . . .
N5 N 0.5455(3) 0.2477(2) 0.60695(18) 0.0162(5) Uani 1 1 d . . . . .
N6 N 0.0807(3) 0.0187(3) 1.1464(2) 0.0270(6) Uani 1 1 d . . . . .
C1 C 0.4478(3) 0.2806(3) 0.2941(2) 0.0164(5) Uani 1 1 d . . . . .
C2 C 0.5699(3) 0.3257(3) 0.1976(2) 0.0164(5) Uani 1 1 d . . . . .
C3 C 0.8909(3) 0.4597(3) 0.2552(2) 0.0144(5) Uani 1 1 d . . . . .
C4 C 0.9967(3) 0.4498(3) 0.1583(2) 0.0166(5) Uani 1 1 d . . . . .
H4 H 0.969296 0.403392 0.110703 0.020 Uiso 1 1 calc R U . . .
C5 C 1.1397(3) 0.5066(3) 0.1317(2) 0.0206(6) Uani 1 1 d . . . . .
H5 H 1.210114 0.498473 0.066290 0.025 Uiso 1 1 calc R U . . .
C6 C 1.1816(3) 0.5754(3) 0.1998(2) 0.0201(6) Uani 1 1 d . . . . .
H6 H 1.281581 0.612127 0.182552 0.024 Uiso 1 1 calc R U . . .
C7 C 1.0758(3) 0.5902(3) 0.2934(2) 0.0187(6) Uani 1 1 d . . . . .
H7 H 1.102743 0.640154 0.338552 0.022 Uiso 1 1 calc R U . . .
C8 C 0.9301(3) 0.5328(3) 0.3225(2) 0.0141(5) Uani 1 1 d . . . . .
C9 C 0.8220(3) 0.5586(3) 0.4236(2) 0.0161(5) Uani 1 1 d . . . . .
C10 C 0.5390(3) 0.3239(3) 0.0901(2) 0.0189(6) Uani 1 1 d . . . . .
C11 C 0.1915(3) 0.1990(3) 0.3479(2) 0.0224(6) Uani 1 1 d . . . . .
H11A H 0.113443 0.169133 0.314820 0.034 Uiso 1 1 calc R U . . .
H11B H 0.144883 0.276610 0.375531 0.034 Uiso 1 1 calc R U . . .
H11C H 0.224395 0.123131 0.411121 0.034 Uiso 1 1 calc R U . . .
C12 C 0.5053(3) 0.3261(3) 0.6766(2) 0.0161(5) Uani 1 1 d . . . . .
H12 H 0.540973 0.415716 0.652700 0.019 Uiso 1 1 calc R U . . .
C13 C 0.4142(3) 0.2820(3) 0.7819(2) 0.0168(5) Uani 1 1 d . . . . .
H13 H 0.386373 0.341545 0.828056 0.020 Uiso 1 1 calc R U . . .
C14 C 0.3636(3) 0.1500(3) 0.8198(2) 0.0164(6) Uani 1 1 d . . . . .
C15 C 0.4095(3) 0.0669(3) 0.7489(2) 0.0222(6) Uani 1 1 d . . . . .
H15 H 0.379977 -0.024707 0.772225 0.027 Uiso 1 1 calc R U . . .
C16 C 0.4987(3) 0.1195(3) 0.6440(2) 0.0207(6) Uani 1 1 d . . . . .
H16 H 0.528227 0.062358 0.596053 0.025 Uiso 1 1 calc R U . . .
C17 C 0.2635(3) 0.1026(3) 0.9326(2) 0.0166(5) Uani 1 1 d . . . . .
C18 C 0.3029(3) -0.0202(3) 1.0115(2) 0.0220(6) Uani 1 1 d . . . . .
H18 H 0.391037 -0.078776 0.993337 0.026 Uiso 1 1 calc R U . . .
C19 C 0.2106(4) -0.0556(3) 1.1176(2) 0.0276(7) Uani 1 1 d . . . . .
H19 H 0.241735 -0.137070 1.172615 0.033 Uiso 1 1 calc R U . . .
C20 C 0.0411(4) 0.1333(3) 1.0681(3) 0.0276(7) Uani 1 1 d . . . . .
H20 H -0.052996 0.185773 1.085991 0.033 Uiso 1 1 calc R U . . .
C21 C 0.1293(3) 0.1804(3) 0.9620(2) 0.0243(6) Uani 1 1 d . . . . .
H21 H 0.098233 0.264849 0.910132 0.029 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 O1 1.9320(19) . ?
Cu1 N1 1.951(2) . ?
Cu1 N3 1.970(2) . ?
Cu1 N5 2.055(2) . ?
Cu1 O4 2.343(2) . ?
O1 C9 1.282(3) . ?
O2 C9 1.245(3) . ?
O3 C1 1.335(3) . ?
O3 C11 1.443(3) . ?
O4 H4A 0.8499 . ?
O4 H4B 0.8500 . ?
O5 H5A 0.8501 . ?
O5 H5B 0.8499 . ?
N1 C1 1.282(4) . ?
N1 H1N 0.8744 . ?
N2 N3 1.300(3) . ?
N2 C2 1.327(3) . ?
N3 C3 1.434(3) . ?
N4 C10 1.146(4) . ?
N5 C12 1.341(3) . ?
N5 C16 1.344(3) . ?
N6 C20 1.331(4) . ?
N6 C19 1.336(4) . ?
C1 C2 1.453(4) . ?
C2 C10 1.430(4) . ?
C3 C8 1.402(4) . ?
C3 C4 1.408(4) . ?
C4 C5 1.377(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.390(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.400(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.508(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.385(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.392(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.395(4) . ?
C14 C17 1.492(3) . ?
C15 C16 1.385(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C21 1.384(4) . ?
C17 C18 1.388(4) . ?
C18 C19 1.390(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.384(4) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?

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 N1 145.84(9) . . ?
O1 Cu1 N3 92.56(8) . . ?
N1 Cu1 N3 91.27(9) . . ?
O1 Cu1 N5 89.17(8) . . ?
N1 Cu1 N5 89.27(9) . . ?
N3 Cu1 N5 176.08(9) . . ?
O1 Cu1 O4 106.59(8) . . ?
N1 Cu1 O4 107.30(9) . . ?
N3 Cu1 O4 90.51(8) . . ?
N5 Cu1 O4 85.62(8) . . ?
C9 O1 Cu1 128.77(17) . . ?
C1 O3 C11 117.8(2) . . ?
Cu1 O4 H4A 130.8 . . ?
Cu1 O4 H4B 124.8 . . ?
H4A O4 H4B 104.3 . . ?
H5A O5 H5B 101.0 . . ?
C1 N1 Cu1 126.73(19) . . ?
C1 N1 H1N 114.0 . . ?
Cu1 N1 H1N 118.6 . . ?
N3 N2 C2 122.8(2) . . ?
N2 N3 C3 111.7(2) . . ?
N2 N3 Cu1 127.27(17) . . ?
C3 N3 Cu1 120.61(17) . . ?
C12 N5 C16 117.7(2) . . ?
C12 N5 Cu1 120.79(17) . . ?
C16 N5 Cu1 120.79(18) . . ?
C20 N6 C19 116.9(2) . . ?
N1 C1 O3 126.9(2) . . ?
N1 C1 C2 122.4(2) . . ?
O3 C1 C2 110.7(2) . . ?
N2 C2 C10 114.6(2) . . ?
N2 C2 C1 128.2(2) . . ?
C10 C2 C1 116.9(2) . . ?
C8 C3 C4 119.1(2) . . ?
C8 C3 N3 121.0(2) . . ?
C4 C3 N3 119.9(2) . . ?
C5 C4 C3 120.8(3) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C7 119.3(3) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C6 C7 C8 121.3(3) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C7 C8 C3 119.0(2) . . ?
C7 C8 C9 116.9(2) . . ?
C3 C8 C9 124.0(2) . . ?
O2 C9 O1 122.6(2) . . ?
O2 C9 C8 118.9(2) . . ?
O1 C9 C8 118.5(2) . . ?
N4 C10 C2 179.0(3) . . ?
O3 C11 H11A 109.5 . . ?
O3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N5 C12 C13 122.8(2) . . ?
N5 C12 H12 118.6 . . ?
C13 C12 H12 118.6 . . ?
C12 C13 C14 119.6(3) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 117.6(2) . . ?
C13 C14 C17 119.9(2) . . ?
C15 C14 C17 122.6(2) . . ?
C16 C15 C14 119.2(2) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
N5 C16 C15 123.1(3) . . ?
N5 C16 H16 118.5 . . ?
C15 C16 H16 118.5 . . ?
C21 C17 C18 118.0(2) . . ?
C21 C17 C14 120.9(2) . . ?
C18 C17 C14 121.0(2) . . ?
C17 C18 C19 118.6(3) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 H18 120.7 . . ?
N6 C19 C18 123.6(3) . . ?
N6 C19 H19 118.2 . . ?
C18 C19 H19 118.2 . . ?
N6 C20 C21 123.8(3) . . ?
N6 C20 H20 118.1 . . ?
C21 C20 H20 118.1 . . ?
C20 C21 C17 119.0(3) . . ?
C20 C21 H21 120.5 . . ?
C17 C21 H21 120.5 . . ?

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
C2 N2 N3 C3 179.7(2) . . . . ?
C2 N2 N3 Cu1 7.1(4) . . . . ?
Cu1 N1 C1 O3 175.70(19) . . . . ?
Cu1 N1 C1 C2 -5.8(4) . . . . ?
C11 O3 C1 N1 1.7(4) . . . . ?
C11 O3 C1 C2 -177.0(2) . . . . ?
N3 N2 C2 C10 176.3(2) . . . . ?
N3 N2 C2 C1 3.3(4) . . . . ?
N1 C1 C2 N2 -4.0(4) . . . . ?
O3 C1 C2 N2 174.7(3) . . . . ?
N1 C1 C2 C10 -176.9(3) . . . . ?
O3 C1 C2 C10 1.8(3) . . . . ?
N2 N3 C3 C8 155.9(2) . . . . ?
Cu1 N3 C3 C8 -31.0(3) . . . . ?
N2 N3 C3 C4 -22.7(3) . . . . ?
Cu1 N3 C3 C4 150.5(2) . . . . ?
C8 C3 C4 C5 2.4(4) . . . . ?
N3 C3 C4 C5 -179.0(2) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C4 C5 C6 C7 -1.9(4) . . . . ?
C5 C6 C7 C8 2.2(4) . . . . ?
C6 C7 C8 C3 -0.3(4) . . . . ?
C6 C7 C8 C9 -178.2(2) . . . . ?
C4 C3 C8 C7 -2.0(4) . . . . ?
N3 C3 C8 C7 179.4(2) . . . . ?
C4 C3 C8 C9 175.7(2) . . . . ?
N3 C3 C8 C9 -2.8(4) . . . . ?
Cu1 O1 C9 O2 153.5(2) . . . . ?
Cu1 O1 C9 C8 -27.5(3) . . . . ?
C7 C8 C9 O2 31.0(4) . . . . ?
C3 C8 C9 O2 -146.8(3) . . . . ?
C7 C8 C9 O1 -148.0(2) . . . . ?
C3 C8 C9 O1 34.2(4) . . . . ?
C16 N5 C12 C13 -2.3(4) . . . . ?
Cu1 N5 C12 C13 167.7(2) . . . . ?
N5 C12 C13 C14 1.4(4) . . . . ?
C12 C13 C14 C15 0.6(4) . . . . ?
C12 C13 C14 C17 -179.2(2) . . . . ?
C13 C14 C15 C16 -1.7(4) . . . . ?
C17 C14 C15 C16 178.1(3) . . . . ?
C12 N5 C16 C15 1.2(4) . . . . ?
Cu1 N5 C16 C15 -168.8(2) . . . . ?
C14 C15 C16 N5 0.8(4) . . . . ?
C13 C14 C17 C21 50.7(4) . . . . ?
C15 C14 C17 C21 -129.1(3) . . . . ?
C13 C14 C17 C18 -128.7(3) . . . . ?
C15 C14 C17 C18 51.5(4) . . . . ?
C21 C17 C18 C19 -3.1(4) . . . . ?
C14 C17 C18 C19 176.3(3) . . . . ?
C20 N6 C19 C18 -0.9(5) . . . . ?
C17 C18 C19 N6 3.6(5) . . . . ?
C19 N6 C20 C21 -2.3(5) . . . . ?
N6 C20 C21 C17 2.6(5) . . . . ?
C18 C17 C21 C20 0.3(4) . . . . ?
C14 C17 C21 C20 -179.1(3) . . . . ?

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
O4 H4A O5 0.85 2.04 2.869(3) 164.0 1_545 yes
O4 H4B O5 0.85 2.01 2.853(3) 168.9 2_766 yes
O5 H5A N6 0.85 1.96 2.808(3) 174.4 1_664 yes
O5 H5B O2 0.85 1.97 2.770(3) 156.3 . yes
N1 H1N O2 0.87 2.17 2.997(3) 157.9 2_666 yes

_refine_diff_density_max         0.384
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.077

####################################################################### 
# 
# 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_PA12_A
_database_code_depnum_ccdc_archive 'CCDC 2234589'
loop_
_audit_author_name
_audit_author_address
'Atash Gurbanov'
;Instituto Superior Tecnico
Portugal
;
_audit_update_record             
;
2023-01-05 deposited with the CCDC.	2023-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H12 Cu N6 O3'
_chemical_formula_sum            'C14 H12 Cu N6 O3'
_chemical_formula_weight         375.84

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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3848(3)
_cell_length_b                   8.9939(4)
_cell_length_c                   11.1413(5)
_cell_angle_alpha                102.733(2)
_cell_angle_beta                 90.338(2)
_cell_angle_gamma                113.054(2)
_cell_volume                     750.08(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9973
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      26.35

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_F_000             382
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    1.483
_shelx_estimated_absorpt_T_min   0.727
_shelx_estimated_absorpt_T_max   0.819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.723
_exptl_absorpt_correction_T_max  0.802
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest PHOTON 100 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25094
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.770
_diffrn_reflns_theta_max         26.380
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             3032
_reflns_number_gt                2891
_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'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0270P)²+0.3722P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3032
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0220
_refine_ls_R_factor_gt           0.0207
_refine_ls_wR_factor_ref         0.0580
_refine_ls_wR_factor_gt          0.0571
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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 0.45844(2) 0.54352(2) 0.84048(2) 0.02618(7) Uani 1 1 d . . . . .
O1 O 0.28706(14) 0.49518(14) 0.95480(10) 0.0359(3) Uani 1 1 d . . . . .
O2 O 0.05743(14) 0.32850(15) 1.02546(10) 0.0368(3) Uani 1 1 d . . . . .
O3 O 0.82631(14) 0.50288(15) 0.60255(10) 0.0360(3) Uani 1 1 d . . . . .
N1 N 0.66869(17) 0.54720(17) 0.76901(12) 0.0300(3) Uani 1 1 d . . . . .
H1N H 0.767800 0.601304 0.817112 0.036 Uiso 1 1 d R U . . .
N2 N 0.36111(17) 0.31159(16) 0.59711(12) 0.0292(3) Uani 1 1 d . . . . .
N3 N 0.31030(16) 0.36142(15) 0.70327(11) 0.0267(3) Uani 1 1 d . . . . .
N4 N 0.5718(2) 0.2538(2) 0.34881(15) 0.0550(5) Uani 1 1 d . . . . .
N5 N 0.58551(17) 0.76885(16) 0.95204(12) 0.0288(3) Uani 1 1 d . . . . .
N6 N 0.77385(19) 1.02673(17) 1.02117(14) 0.0388(3) Uani 1 1 d . . . . .
H6N H 0.856736 1.122292 1.016353 0.047 Uiso 1 1 d R U . . .
C1 C 0.67948(19) 0.48102(18) 0.65687(14) 0.0271(3) Uani 1 1 d . . . . .
C2 C 0.5257(2) 0.36759(19) 0.57351(14) 0.0294(3) Uani 1 1 d . . . . .
C3 C 0.12473(19) 0.28660(18) 0.70056(14) 0.0270(3) Uani 1 1 d . . . . .
C4 C 0.0201(2) 0.1988(2) 0.58810(15) 0.0371(4) Uani 1 1 d . . . . .
H4 H 0.072674 0.186512 0.515440 0.045 Uiso 1 1 calc R U . . .
C5 C -0.1593(2) 0.1305(2) 0.58337(17) 0.0418(4) Uani 1 1 d . . . . .
H5 H -0.225815 0.070122 0.508171 0.050 Uiso 1 1 calc R U . . .
C6 C -0.2411(2) 0.1511(2) 0.68949(17) 0.0393(4) Uani 1 1 d . . . . .
H6 H -0.361979 0.108937 0.685783 0.047 Uiso 1 1 calc R U . . .
C7 C -0.1401(2) 0.2351(2) 0.80063(16) 0.0339(3) Uani 1 1 d . . . . .
H7 H -0.194883 0.248568 0.872093 0.041 Uiso 1 1 calc R U . . .
C8 C 0.04234(19) 0.30094(18) 0.80976(14) 0.0273(3) Uani 1 1 d . . . . .
C9 C 0.1348(2) 0.37887(19) 0.93782(14) 0.0288(3) Uani 1 1 d . . . . .
C10 C 0.5512(2) 0.3026(2) 0.44865(15) 0.0365(4) Uani 1 1 d . . . . .
C11 C 0.9889(2) 0.6183(2) 0.67291(17) 0.0414(4) Uani 1 1 d . . . . .
H11A H 1.082616 0.625273 0.622280 0.062 Uiso 1 1 calc R U . . .
H11B H 1.006505 0.580369 0.743951 0.062 Uiso 1 1 calc R U . . .
H11C H 0.986079 0.726202 0.699419 0.062 Uiso 1 1 calc R U . . .
C12 C 0.5636(2) 0.8241(2) 1.07333(15) 0.0349(4) Uani 1 1 d . . . . .
H12 H 0.482333 0.761746 1.118767 0.042 Uiso 1 1 calc R U . . .
C13 C 0.6789(2) 0.9837(2) 1.11617(17) 0.0433(4) Uani 1 1 d . . . . .
H13 H 0.691009 1.050912 1.195062 0.052 Uiso 1 1 calc R U . . .
C14 C 0.7137(2) 0.8952(2) 0.92457(16) 0.0361(4) Uani 1 1 d . . . . .
H14 H 0.756613 0.892732 0.847701 0.043 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 O1 1.9112(11) . ?
Cu1 N1 1.9301(13) . ?
Cu1 N3 1.9603(12) . ?
Cu1 N5 1.9925(13) . ?
O1 C9 1.2743(18) . ?
O2 C9 1.2457(19) . ?
O3 C1 1.3387(18) . ?
O3 C11 1.439(2) . ?
N1 C1 1.2803(19) . ?
N1 H1N 0.8818 . ?
N2 N3 1.3051(17) . ?
N2 C2 1.321(2) . ?
N3 C3 1.4301(19) . ?
N4 C10 1.143(2) . ?
N5 C14 1.319(2) . ?
N5 C12 1.373(2) . ?
N6 C14 1.333(2) . ?
N6 C13 1.361(2) . ?
N6 H6N 0.8818 . ?
C1 C2 1.450(2) . ?
C2 C10 1.437(2) . ?
C3 C4 1.404(2) . ?
C3 C8 1.409(2) . ?
C4 C5 1.379(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.377(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.401(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.500(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.352(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14 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
O1 Cu1 N1 155.20(6) . . ?
O1 Cu1 N3 94.19(5) . . ?
N1 Cu1 N3 92.22(5) . . ?
O1 Cu1 N5 89.31(5) . . ?
N1 Cu1 N5 91.77(5) . . ?
N3 Cu1 N5 162.41(6) . . ?
C9 O1 Cu1 128.80(10) . . ?
C1 O3 C11 118.07(12) . . ?
C1 N1 Cu1 126.29(11) . . ?
C1 N1 H1N 116.1 . . ?
Cu1 N1 H1N 117.6 . . ?
N3 N2 C2 123.31(13) . . ?
N2 N3 C3 111.22(12) . . ?
N2 N3 Cu1 125.49(10) . . ?
C3 N3 Cu1 122.44(9) . . ?
C14 N5 C12 105.62(13) . . ?
C14 N5 Cu1 126.39(11) . . ?
C12 N5 Cu1 127.95(11) . . ?
C14 N6 C13 107.40(14) . . ?
C14 N6 H6N 122.0 . . ?
C13 N6 H6N 130.5 . . ?
N1 C1 O3 126.30(14) . . ?
N1 C1 C2 121.66(14) . . ?
O3 C1 C2 112.04(13) . . ?
N2 C2 C10 113.99(14) . . ?
N2 C2 C1 128.54(14) . . ?
C10 C2 C1 117.46(14) . . ?
C4 C3 C8 118.40(14) . . ?
C4 C3 N3 120.51(13) . . ?
C8 C3 N3 121.08(13) . . ?
C5 C4 C3 121.23(16) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 120.61(16) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 118.76(16) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C6 C7 C8 122.24(15) . . ?
C6 C7 H7 118.9 . . ?
C8 C7 H7 118.9 . . ?
C7 C8 C3 118.64(14) . . ?
C7 C8 C9 116.31(13) . . ?
C3 C8 C9 125.04(13) . . ?
O2 C9 O1 121.87(14) . . ?
O2 C9 C8 118.13(13) . . ?
O1 C9 C8 119.99(13) . . ?
N4 C10 C2 178.7(2) . . ?
O3 C11 H11A 109.5 . . ?
O3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 N5 109.13(14) . . ?
C13 C12 H12 125.4 . . ?
N5 C12 H12 125.4 . . ?
C12 C13 N6 106.54(15) . . ?
C12 C13 H13 126.7 . . ?
N6 C13 H13 126.7 . . ?
N5 C14 N6 111.30(14) . . ?
N5 C14 H14 124.4 . . ?
N6 C14 H14 124.4 . . ?

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
C2 N2 N3 C3 177.00(15) . . . . ?
C2 N2 N3 Cu1 7.4(2) . . . . ?
Cu1 N1 C1 O3 169.92(12) . . . . ?
Cu1 N1 C1 C2 -11.1(2) . . . . ?
C11 O3 C1 N1 -3.7(3) . . . . ?
C11 O3 C1 C2 177.31(15) . . . . ?
N3 N2 C2 C10 -176.79(15) . . . . ?
N3 N2 C2 C1 4.5(3) . . . . ?
N1 C1 C2 N2 -2.6(3) . . . . ?
O3 C1 C2 N2 176.47(16) . . . . ?
N1 C1 C2 C10 178.68(16) . . . . ?
O3 C1 C2 C10 -2.2(2) . . . . ?
N2 N3 C3 C4 -11.2(2) . . . . ?
Cu1 N3 C3 C4 158.84(13) . . . . ?
N2 N3 C3 C8 169.77(14) . . . . ?
Cu1 N3 C3 C8 -20.2(2) . . . . ?
C8 C3 C4 C5 1.2(3) . . . . ?
N3 C3 C4 C5 -177.89(16) . . . . ?
C3 C4 C5 C6 1.9(3) . . . . ?
C4 C5 C6 C7 -2.6(3) . . . . ?
C5 C6 C7 C8 0.3(3) . . . . ?
C6 C7 C8 C3 2.8(2) . . . . ?
C6 C7 C8 C9 -175.91(16) . . . . ?
C4 C3 C8 C7 -3.4(2) . . . . ?
N3 C3 C8 C7 175.65(14) . . . . ?
C4 C3 C8 C9 175.11(15) . . . . ?
N3 C3 C8 C9 -5.8(2) . . . . ?
Cu1 O1 C9 O2 157.31(13) . . . . ?
Cu1 O1 C9 C8 -23.9(2) . . . . ?
C7 C8 C9 O2 26.9(2) . . . . ?
C3 C8 C9 O2 -151.66(16) . . . . ?
C7 C8 C9 O1 -151.89(16) . . . . ?
C3 C8 C9 O1 29.5(2) . . . . ?
C14 N5 C12 C13 0.4(2) . . . . ?
Cu1 N5 C12 C13 178.39(13) . . . . ?
N5 C12 C13 N6 -0.6(2) . . . . ?
C14 N6 C13 C12 0.6(2) . . . . ?
C12 N5 C14 N6 0.0(2) . . . . ?
Cu1 N5 C14 N6 -178.06(12) . . . . ?
C13 N6 C14 N5 -0.3(2) . . . . ?

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
N1 H1N O2 0.88 2.09 2.9268(18) 157.5 2_667 yes
N6 H6N O2 0.88 1.94 2.8124(17) 171.6 1_665 yes

_refine_diff_density_max         0.275
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_5c_a
_database_code_depnum_ccdc_archive 'CCDC 2234592'
loop_
_audit_author_name
_audit_author_address
'Atash Gurbanov'
;Instituto Superior Tecnico
Portugal
;
_audit_update_record             
;
2023-01-05 deposited with the CCDC.	2023-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H13 Cu N5 O3'
_chemical_formula_sum            'C16 H13 Cu N5 O3'
_chemical_formula_weight         386.85

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   7.5563(2)
_cell_length_b                   19.9231(4)
_cell_length_c                   19.9344(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3001.02(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9968
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      26.35

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.712
_exptl_crystal_F_000             1576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    1.484
_shelx_estimated_absorpt_T_min   0.648
_shelx_estimated_absorpt_T_max   0.819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.632
_exptl_absorpt_correction_T_max  0.802
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_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 D8 Quest PHOTON 100 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28483
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.286
_diffrn_reflns_theta_max         26.374
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3074
_reflns_number_gt                2692
_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'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0371P)²+1.6377P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3074
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0249
_refine_ls_wR_factor_ref         0.0695
_refine_ls_wR_factor_gt          0.0659
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.002
_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 0.35669(3) 0.75250(2) 0.42096(2) 0.01684(8) Uani 1 1 d . . . . .
O1 O 0.24557(19) 0.68435(6) 0.47166(6) 0.0256(3) Uani 1 1 d . . . . .
O2 O 0.13127(18) 0.58795(6) 0.50161(6) 0.0252(3) Uani 1 1 d . . . . .
O3 O 0.69726(17) 0.86837(6) 0.30544(6) 0.0220(3) Uani 1 1 d . . . . .
N1 N 0.52694(19) 0.81825(7) 0.38977(7) 0.0182(3) Uani 1 1 d . . . . .
H1N H 0.564251 0.851181 0.418677 0.022 Uiso 1 1 d R U . . .
N2 N 0.45309(18) 0.71546(7) 0.28533(7) 0.0170(3) Uani 1 1 d . . . . .
N3 N 0.39734(19) 0.69347(7) 0.34344(7) 0.0158(3) Uani 1 1 d . . . . .
N4 N 0.6079(2) 0.80178(7) 0.15426(8) 0.0231(3) Uani 1 1 d . . . . .
N5 N 0.2909(2) 0.81503(7) 0.49749(7) 0.0190(3) Uani 1 1 d . . . . .
C1 C 0.5823(2) 0.82249(8) 0.32927(8) 0.0171(3) Uani 1 1 d . . . . .
C2 C 0.5289(2) 0.77502(8) 0.27747(8) 0.0167(3) Uani 1 1 d . . . . .
C3 C 0.3462(2) 0.62445(8) 0.33999(8) 0.0160(3) Uani 1 1 d . . . . .
C4 C 0.3987(2) 0.58552(8) 0.28434(8) 0.0191(3) Uani 1 1 d . . . . .
H4 H 0.468052 0.605500 0.249984 0.023 Uiso 1 1 calc R U . . .
C5 C 0.3508(2) 0.51884(9) 0.27900(9) 0.0219(4) Uani 1 1 d . . . . .
H5 H 0.388158 0.493547 0.241165 0.026 Uiso 1 1 calc R U . . .
C6 C 0.2485(3) 0.48824(9) 0.32831(9) 0.0232(4) Uani 1 1 d . . . . .
H6 H 0.211850 0.442863 0.323685 0.028 Uiso 1 1 calc R U . . .
C7 C 0.2013(2) 0.52524(8) 0.38420(9) 0.0209(4) Uani 1 1 d . . . . .
H7 H 0.132942 0.504423 0.418371 0.025 Uiso 1 1 calc R U . . .
C8 C 0.2513(2) 0.59271(8) 0.39193(8) 0.0169(3) Uani 1 1 d . . . . .
C9 C 0.2054(2) 0.62339(8) 0.45920(8) 0.0181(3) Uani 1 1 d . . . . .
C10 C 0.5738(2) 0.79031(8) 0.20934(9) 0.0183(3) Uani 1 1 d . . . . .
C11 C 0.7762(3) 0.91321(9) 0.35395(9) 0.0249(4) Uani 1 1 d . . . . .
H11A H 0.861265 0.942675 0.331349 0.037 Uiso 1 1 calc R U . . .
H11B H 0.837424 0.886910 0.388419 0.037 Uiso 1 1 calc R U . . .
H11C H 0.683573 0.940448 0.374974 0.037 Uiso 1 1 calc R U . . .
C12 C 0.3335(2) 0.79704(9) 0.56053(9) 0.0210(4) Uani 1 1 d . . . . .
H12 H 0.379641 0.753357 0.568199 0.025 Uiso 1 1 calc R U . . .
C13 C 0.3125(3) 0.83982(9) 0.61448(9) 0.0243(4) Uani 1 1 d . . . . .
H13 H 0.343892 0.825832 0.658453 0.029 Uiso 1 1 calc R U . . .
C14 C 0.2450(3) 0.90329(9) 0.60336(10) 0.0271(4) Uani 1 1 d . . . . .
H14 H 0.230012 0.933643 0.639672 0.033 Uiso 1 1 calc R U . . .
C15 C 0.1995(3) 0.92225(9) 0.53882(10) 0.0279(4) Uani 1 1 d . . . . .
H15 H 0.152155 0.965553 0.530072 0.033 Uiso 1 1 calc R U . . .
C16 C 0.2246(3) 0.87666(9) 0.48737(9) 0.0238(4) Uani 1 1 d . . . . .
H16 H 0.193557 0.889524 0.443018 0.029 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 O1 1.8895(12) . ?
Cu1 N1 1.9384(14) . ?
Cu1 N3 1.9661(14) . ?
Cu1 N5 2.0314(14) . ?
O1 C9 1.276(2) . ?
O2 C9 1.236(2) . ?
O3 C1 1.347(2) . ?
O3 C11 1.445(2) . ?
N1 C1 1.279(2) . ?
N1 H1N 0.9176 . ?
N2 N3 1.3082(19) . ?
N2 C2 1.327(2) . ?
N3 C3 1.430(2) . ?
N4 C10 1.151(2) . ?
N5 C16 1.341(2) . ?
N5 C12 1.346(2) . ?
C1 C2 1.457(2) . ?
C2 C10 1.433(2) . ?
C3 C8 1.409(2) . ?
C3 C4 1.410(2) . ?
C4 C5 1.381(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.383(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.405(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.514(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.381(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.381(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.383(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?

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 N1 162.20(6) . . ?
O1 Cu1 N3 93.44(5) . . ?
N1 Cu1 N3 92.77(6) . . ?
O1 Cu1 N5 86.00(5) . . ?
N1 Cu1 N5 89.36(6) . . ?
N3 Cu1 N5 174.48(6) . . ?
C9 O1 Cu1 133.28(11) . . ?
C1 O3 C11 116.72(13) . . ?
C1 N1 Cu1 124.34(12) . . ?
C1 N1 H1N 116.4 . . ?
Cu1 N1 H1N 119.1 . . ?
N3 N2 C2 122.88(14) . . ?
N2 N3 C3 111.50(13) . . ?
N2 N3 Cu1 123.10(10) . . ?
C3 N3 Cu1 124.80(11) . . ?
C16 N5 C12 118.26(15) . . ?
C16 N5 Cu1 122.67(12) . . ?
C12 N5 Cu1 118.64(12) . . ?
N1 C1 O3 126.02(15) . . ?
N1 C1 C2 122.30(15) . . ?
O3 C1 C2 111.66(14) . . ?
N2 C2 C10 113.85(14) . . ?
N2 C2 C1 128.06(15) . . ?
C10 C2 C1 117.90(15) . . ?
C8 C3 C4 118.31(15) . . ?
C8 C3 N3 122.26(14) . . ?
C4 C3 N3 119.37(15) . . ?
C5 C4 C3 121.06(16) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 120.84(16) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 118.63(16) . . ?
C7 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C6 C7 C8 121.94(16) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 H7 119.0 . . ?
C7 C8 C3 119.05(15) . . ?
C7 C8 C9 114.95(15) . . ?
C3 C8 C9 125.88(14) . . ?
O2 C9 O1 121.23(15) . . ?
O2 C9 C8 118.62(15) . . ?
O1 C9 C8 120.14(15) . . ?
N4 C10 C2 178.84(19) . . ?
O3 C11 H11A 109.5 . . ?
O3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N5 C12 C13 122.35(16) . . ?
N5 C12 H12 118.8 . . ?
C13 C12 H12 118.8 . . ?
C14 C13 C12 118.84(17) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C13 C14 C15 119.38(17) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C16 C15 C14 118.41(17) . . ?
C16 C15 H15 120.8 . . ?
C14 C15 H15 120.8 . . ?
N5 C16 C15 122.75(17) . . ?
N5 C16 H16 118.6 . . ?
C15 C16 H16 118.6 . . ?

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
N1 Cu1 O1 C9 -112.7(2) . . . . ?
N3 Cu1 O1 C9 -2.46(18) . . . . ?
N5 Cu1 O1 C9 172.04(18) . . . . ?
C2 N2 N3 C3 -171.11(15) . . . . ?
C2 N2 N3 Cu1 17.4(2) . . . . ?
Cu1 N1 C1 O3 178.39(12) . . . . ?
Cu1 N1 C1 C2 -3.4(2) . . . . ?
C11 O3 C1 N1 5.6(3) . . . . ?
C11 O3 C1 C2 -172.77(14) . . . . ?
N3 N2 C2 C10 -177.69(15) . . . . ?
N3 N2 C2 C1 7.5(3) . . . . ?
N1 C1 C2 N2 -15.6(3) . . . . ?
O3 C1 C2 N2 162.77(16) . . . . ?
N1 C1 C2 C10 169.76(16) . . . . ?
O3 C1 C2 C10 -11.8(2) . . . . ?
N2 N3 C3 C8 -167.82(15) . . . . ?
Cu1 N3 C3 C8 3.5(2) . . . . ?
N2 N3 C3 C4 15.1(2) . . . . ?
Cu1 N3 C3 C4 -173.58(12) . . . . ?
C8 C3 C4 C5 3.3(2) . . . . ?
N3 C3 C4 C5 -179.54(15) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C4 C5 C6 C7 -2.5(3) . . . . ?
C5 C6 C7 C8 1.0(3) . . . . ?
C6 C7 C8 C3 2.7(3) . . . . ?
C6 C7 C8 C9 -173.76(16) . . . . ?
C4 C3 C8 C7 -4.7(2) . . . . ?
N3 C3 C8 C7 178.22(15) . . . . ?
C4 C3 C8 C9 171.30(16) . . . . ?
N3 C3 C8 C9 -5.8(3) . . . . ?
Cu1 O1 C9 O2 179.97(13) . . . . ?
Cu1 O1 C9 C8 1.1(3) . . . . ?
C7 C8 C9 O2 0.8(2) . . . . ?
C3 C8 C9 O2 -175.36(16) . . . . ?
C7 C8 C9 O1 179.71(16) . . . . ?
C3 C8 C9 O1 3.6(3) . . . . ?
C16 N5 C12 C13 -0.5(3) . . . . ?
Cu1 N5 C12 C13 172.28(14) . . . . ?
N5 C12 C13 C14 0.1(3) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C13 C14 C15 C16 -0.4(3) . . . . ?
C12 N5 C16 C15 0.4(3) . . . . ?
Cu1 N5 C16 C15 -172.06(15) . . . . ?
C14 C15 C16 N5 0.0(3) . . . . ?

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
N1 H1N O2 0.92 2.06 2.9669(18) 168.5 2_566 yes

_refine_diff_density_max         0.311
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_AK38
_database_code_depnum_ccdc_archive 'CCDC 2234593'
loop_
_audit_author_name
_audit_author_address
'Atash Gurbanov'
;Instituto Superior Tecnico
Portugal
;
_audit_update_record             
;
2023-01-05 deposited with the CCDC.	2023-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H34 Cu3 N12 O10 [+ solvent]'
_chemical_formula_sum            'C44 H34 Cu3 N12 O10'
_chemical_formula_weight         1081.45

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   30.947(5)
_cell_length_b                   8.1219(10)
_cell_length_c                   20.211(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.999(7)
_cell_angle_gamma                90
_cell_volume                     4969.1(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3655
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      22.31

_exptl_crystal_description       prism
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_F_000             2196
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.338
_shelx_estimated_absorpt_T_min   0.814
_shelx_estimated_absorpt_T_max   0.878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.801
_exptl_absorpt_correction_T_max  0.865
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest PHOTON 100 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35267
_diffrn_reflns_av_unetI/netI     0.0794
_diffrn_reflns_av_R_equivalents  0.0993
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.031
_diffrn_reflns_theta_max         25.598
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4626
_reflns_number_gt                2508
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_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)+(0.0856P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4626
_refine_ls_number_parameters     314
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1192
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.1590
_refine_ls_wR_factor_gt          0.1304
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_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 0.73739(2) 0.71928(8) 0.31587(3) 0.0520(3) Uani 1 1 d . . . . .
Cu2 Cu 0.500000 1.000000 0.500000 0.0552(3) Uani 1 2 d S . P . .
O5 O 0.79397(13) 0.4388(5) 0.48394(17) 0.0664(11) Uani 1 1 d . . . . .
N2 N 0.69416(14) 0.6647(5) 0.42832(19) 0.0480(11) Uani 1 1 d . . . . .
N1 N 0.69054(13) 0.7239(5) 0.36693(19) 0.0440(10) Uani 1 1 d . . . . .
O2 O 0.64849(13) 0.9484(6) 0.17415(19) 0.0808(13) Uani 1 1 d . . . . .
O3 O 0.56784(14) 0.8723(5) 0.4859(2) 0.0748(12) Uani 1 1 d . . . . .
O1 O 0.70076(14) 0.8129(6) 0.23863(18) 0.0769(13) Uani 1 1 d . . . . .
N5 N 0.78670(15) 0.7620(6) 0.2649(2) 0.0562(12) Uani 1 1 d . . . . .
O4 O 0.51514(14) 0.9816(5) 0.4065(2) 0.0751(12) Uani 1 1 d . . . . .
N3 N 0.77442(14) 0.5747(5) 0.37922(19) 0.0541(11) Uani 1 1 d . . . . .
H3N H 0.797563 0.535470 0.367584 0.065 Uiso 1 1 calc R U . . .
N6 N 0.46572(16) 0.7900(5) 0.4854(3) 0.0601(12) Uani 1 1 d . . . . .
C1 C 0.64947(17) 0.8065(6) 0.3458(2) 0.0440(12) Uani 1 1 d . . . . .
C2 C 0.63594(17) 0.8759(6) 0.2807(2) 0.0471(13) Uani 1 1 d . . . . .
C6 C 0.62015(18) 0.8217(6) 0.3905(3) 0.0508(13) Uani 1 1 d . . . . .
H6 H 0.628238 0.776151 0.433493 0.061 Uiso 1 1 calc R U . . .
C13 C 0.72827(18) 0.5801(6) 0.4599(2) 0.0473(13) Uani 1 1 d . . . . .
C3 C 0.59530(19) 0.9518(7) 0.2648(3) 0.0616(15) Uani 1 1 d . . . . .
H3 H 0.586257 0.996260 0.221713 0.074 Uiso 1 1 calc R U . . .
C5 C 0.58072(19) 0.9000(6) 0.3733(3) 0.0560(15) Uani 1 1 d . . . . .
C14 C 0.76749(18) 0.5321(6) 0.4371(3) 0.0532(14) Uani 1 1 d . . . . .
C4 C 0.56753(19) 0.9648(7) 0.3093(3) 0.0629(15) Uani 1 1 d . . . . .
H4 H 0.540257 1.016534 0.296474 0.076 Uiso 1 1 calc R U . . .
N4 N 0.72077(18) 0.5090(7) 0.5810(2) 0.0822(16) Uani 1 1 d . . . . .
C15 C 0.72486(18) 0.5355(7) 0.5279(3) 0.0586(15) Uani 1 1 d . . . . .
C22 C 0.66288(19) 0.8791(7) 0.2275(3) 0.0554(14) Uani 1 1 d . . . . .
C21 C 0.7807(2) 0.7150(7) 0.2000(3) 0.0654(16) Uani 1 1 d . . . . .
H21 H 0.754919 0.659237 0.180799 0.079 Uiso 1 1 calc R U . . .
C20 C 0.8107(2) 0.7451(8) 0.1610(3) 0.0716(19) Uani 1 1 d . . . . .
H20 H 0.805647 0.708279 0.116504 0.086 Uiso 1 1 calc R U . . .
C16 C 0.8348(2) 0.3779(8) 0.4704(3) 0.0782(18) Uani 1 1 d . . . . .
H16A H 0.850360 0.317941 0.508986 0.117 Uiso 1 1 calc R U . . .
H16B H 0.852543 0.468655 0.461333 0.117 Uiso 1 1 calc R U . . .
H16C H 0.828714 0.306228 0.431789 0.117 Uiso 1 1 calc R U . . .
C7 C 0.5532(2) 0.9166(7) 0.4277(4) 0.0603(16) Uani 1 1 d . . . . .
C19 C 0.8478(3) 0.8288(9) 0.1874(4) 0.093(2) Uani 1 1 d . . . . .
H19 H 0.867907 0.854382 0.160551 0.111 Uiso 1 1 calc R U . . .
C8 C 0.4361(2) 0.7636(8) 0.4304(4) 0.0799(19) Uani 1 1 d . . . . .
H8 H 0.432478 0.841914 0.396124 0.096 Uiso 1 1 calc R U . . .
C17 C 0.8231(2) 0.8414(9) 0.2909(3) 0.086(2) Uani 1 1 d . . . . .
H17 H 0.827471 0.876090 0.335666 0.104 Uiso 1 1 calc R U . . .
C18 C 0.8559(2) 0.8765(9) 0.2543(4) 0.107(3) Uani 1 1 d . . . . .
H18 H 0.882011 0.929540 0.274298 0.128 Uiso 1 1 calc R U . . .
C12 C 0.4704(3) 0.6749(9) 0.5342(4) 0.104(3) Uani 1 1 d . . . . .
H12 H 0.491362 0.690782 0.573842 0.125 Uiso 1 1 calc R U . . .
C9 C 0.4099(3) 0.6251(11) 0.4207(4) 0.100(2) Uani 1 1 d . . . . .
H9 H 0.388961 0.610915 0.380898 0.121 Uiso 1 1 calc R U . . .
C10 C 0.4152(3) 0.5102(9) 0.4700(6) 0.111(3) Uani 1 1 d . . . . .
H10 H 0.398172 0.414916 0.464264 0.133 Uiso 1 1 calc R U . . .
C11 C 0.4452(3) 0.5346(10) 0.5271(5) 0.129(3) Uani 1 1 d . . . . .
H11 H 0.448858 0.457196 0.561769 0.155 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 O1 1.888(4) . ?
Cu1 N3 1.929(4) . ?
Cu1 N1 1.947(4) . ?
Cu1 N5 2.041(4) . ?
Cu2 N6 1.998(5) . ?
Cu2 N6 1.998(5) 5_676 ?
Cu2 O4 2.044(4) . ?
Cu2 O4 2.044(4) 5_676 ?
Cu2 O3 2.411(4) . ?
Cu2 O3 2.411(4) 5_676 ?
Cu2 C7 2.511(5) 5_676 ?
Cu2 C7 2.512(5) . ?
O5 C14 1.349(6) . ?
O5 C16 1.435(6) . ?
N2 C13 1.309(6) . ?
N2 N1 1.314(5) . ?
N1 C1 1.422(6) . ?
O2 C22 1.216(6) . ?
O3 C7 1.223(7) . ?
O1 C22 1.266(6) . ?
N5 C17 1.311(7) . ?
N5 C21 1.342(7) . ?
O4 C7 1.281(7) . ?
N3 C14 1.279(6) . ?
N3 H3N 0.8600 . ?
N6 C8 1.304(8) . ?
N6 C12 1.344(8) . ?
C1 C2 1.411(7) . ?
C1 C6 1.413(6) . ?
C2 C3 1.377(7) . ?
C2 C22 1.493(6) . ?
C6 C5 1.356(7) . ?
C6 H6 0.9300 . ?
C13 C14 1.440(7) . ?
C13 C15 1.445(7) . ?
C3 C4 1.372(7) . ?
C3 H3 0.9300 . ?
C5 C4 1.377(7) . ?
C5 C7 1.530(7) . ?
C4 H4 0.9300 . ?
N4 C15 1.129(6) . ?
C21 C20 1.358(7) . ?
C21 H21 0.9300 . ?
C20 C19 1.345(9) . ?
C20 H20 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C19 C18 1.379(9) . ?
C19 H19 0.9300 . ?
C8 C9 1.376(9) . ?
C8 H8 0.9300 . ?
C17 C18 1.404(8) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C12 C11 1.372(10) . ?
C12 H12 0.9300 . ?
C9 C10 1.350(10) . ?
C9 H9 0.9300 . ?
C10 C11 1.336(11) . ?
C10 H10 0.9300 . ?
C11 H11 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
O1 Cu1 N3 164.95(18) . . ?
O1 Cu1 N1 92.59(16) . . ?
N3 Cu1 N1 93.72(17) . . ?
O1 Cu1 N5 84.11(17) . . ?
N3 Cu1 N5 92.03(18) . . ?
N1 Cu1 N5 169.04(18) . . ?
N6 Cu2 N6 180.0 . 5_676 ?
N6 Cu2 O4 91.06(17) . . ?
N6 Cu2 O4 88.94(17) 5_676 . ?
N6 Cu2 O4 88.94(17) . 5_676 ?
N6 Cu2 O4 91.06(17) 5_676 5_676 ?
O4 Cu2 O4 180.0 . 5_676 ?
N6 Cu2 O3 93.69(16) . . ?
N6 Cu2 O3 86.31(16) 5_676 . ?
O4 Cu2 O3 59.14(15) . . ?
O4 Cu2 O3 120.86(15) 5_676 . ?
N6 Cu2 O3 86.31(16) . 5_676 ?
N6 Cu2 O3 93.69(16) 5_676 5_676 ?
O4 Cu2 O3 120.86(15) . 5_676 ?
O4 Cu2 O3 59.14(15) 5_676 5_676 ?
O3 Cu2 O3 180.0 . 5_676 ?
N6 Cu2 C7 85.61(17) . 5_676 ?
N6 Cu2 C7 94.39(17) 5_676 5_676 ?
O4 Cu2 C7 149.47(19) . 5_676 ?
O4 Cu2 C7 30.53(19) 5_676 5_676 ?
O3 Cu2 C7 151.31(16) . 5_676 ?
O3 Cu2 C7 28.69(16) 5_676 5_676 ?
N6 Cu2 C7 94.39(17) . . ?
N6 Cu2 C7 85.61(17) 5_676 . ?
O4 Cu2 C7 30.53(19) . . ?
O4 Cu2 C7 149.47(19) 5_676 . ?
O3 Cu2 C7 28.69(16) . . ?
O3 Cu2 C7 151.31(16) 5_676 . ?
C7 Cu2 C7 180.0 5_676 . ?
C14 O5 C16 119.3(4) . . ?
C13 N2 N1 123.7(4) . . ?
N2 N1 C1 110.6(4) . . ?
N2 N1 Cu1 124.5(3) . . ?
C1 N1 Cu1 124.5(3) . . ?
C7 O3 Cu2 80.2(3) . . ?
C22 O1 Cu1 133.8(3) . . ?
C17 N5 C21 117.7(5) . . ?
C17 N5 Cu1 123.5(4) . . ?
C21 N5 Cu1 118.7(4) . . ?
C7 O4 Cu2 95.3(4) . . ?
C14 N3 Cu1 125.6(4) . . ?
C14 N3 H3N 117.2 . . ?
Cu1 N3 H3N 117.2 . . ?
C8 N6 C12 117.4(6) . . ?
C8 N6 Cu2 121.6(4) . . ?
C12 N6 Cu2 120.9(5) . . ?
C2 C1 C6 117.1(5) . . ?
C2 C1 N1 122.9(4) . . ?
C6 C1 N1 120.1(4) . . ?
C3 C2 C1 118.5(4) . . ?
C3 C2 C22 116.3(5) . . ?
C1 C2 C22 125.2(5) . . ?
C5 C6 C1 122.7(5) . . ?
C5 C6 H6 118.6 . . ?
C1 C6 H6 118.6 . . ?
N2 C13 C14 129.3(4) . . ?
N2 C13 C15 112.6(4) . . ?
C14 C13 C15 118.0(5) . . ?
C4 C3 C2 123.2(5) . . ?
C4 C3 H3 118.4 . . ?
C2 C3 H3 118.4 . . ?
C6 C5 C4 119.7(5) . . ?
C6 C5 C7 117.5(5) . . ?
C4 C5 C7 122.8(6) . . ?
N3 C14 O5 126.9(5) . . ?
N3 C14 C13 122.2(5) . . ?
O5 C14 C13 110.9(4) . . ?
C3 C4 C5 118.9(5) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
N4 C15 C13 175.9(6) . . ?
O2 C22 O1 120.6(5) . . ?
O2 C22 C2 119.4(5) . . ?
O1 C22 C2 120.0(5) . . ?
N5 C21 C20 122.9(6) . . ?
N5 C21 H21 118.5 . . ?
C20 C21 H21 118.5 . . ?
C19 C20 C21 119.4(6) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
O5 C16 H16A 109.5 . . ?
O5 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O5 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C7 O4 124.9(5) . . ?
O3 C7 C5 121.1(6) . . ?
O4 C7 C5 114.0(6) . . ?
O3 C7 Cu2 71.1(3) . . ?
O4 C7 Cu2 54.1(3) . . ?
C5 C7 Cu2 166.4(5) . . ?
C20 C19 C18 119.8(6) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
N6 C8 C9 123.0(7) . . ?
N6 C8 H8 118.5 . . ?
C9 C8 H8 118.5 . . ?
N5 C17 C18 123.0(6) . . ?
N5 C17 H17 118.5 . . ?
C18 C17 H17 118.5 . . ?
C19 C18 C17 117.1(7) . . ?
C19 C18 H18 121.4 . . ?
C17 C18 H18 121.4 . . ?
N6 C12 C11 122.0(7) . . ?
N6 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C10 C9 C8 118.9(7) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C11 C10 C9 119.4(8) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C12 119.3(8) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?

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
C13 N2 N1 C1 178.6(4) . . . . ?
C13 N2 N1 Cu1 -7.3(6) . . . . ?
N3 Cu1 O1 C22 125.1(7) . . . . ?
N1 Cu1 O1 C22 10.4(6) . . . . ?
N5 Cu1 O1 C22 -159.2(6) . . . . ?
N2 N1 C1 C2 -177.2(4) . . . . ?
Cu1 N1 C1 C2 8.8(6) . . . . ?
N2 N1 C1 C6 2.7(6) . . . . ?
Cu1 N1 C1 C6 -171.3(3) . . . . ?
C6 C1 C2 C3 -0.7(7) . . . . ?
N1 C1 C2 C3 179.2(4) . . . . ?
C6 C1 C2 C22 177.3(5) . . . . ?
N1 C1 C2 C22 -2.8(8) . . . . ?
C2 C1 C6 C5 -0.5(7) . . . . ?
N1 C1 C6 C5 179.5(4) . . . . ?
N1 N2 C13 C14 -0.7(8) . . . . ?
N1 N2 C13 C15 177.5(4) . . . . ?
C1 C2 C3 C4 0.8(8) . . . . ?
C22 C2 C3 C4 -177.3(5) . . . . ?
C1 C6 C5 C4 1.7(8) . . . . ?
C1 C6 C5 C7 -176.6(4) . . . . ?
Cu1 N3 C14 O5 -176.1(4) . . . . ?
Cu1 N3 C14 C13 4.6(7) . . . . ?
C16 O5 C14 N3 0.3(8) . . . . ?
C16 O5 C14 C13 179.7(5) . . . . ?
N2 C13 C14 N3 2.3(9) . . . . ?
C15 C13 C14 N3 -175.8(5) . . . . ?
N2 C13 C14 O5 -177.1(5) . . . . ?
C15 C13 C14 O5 4.7(7) . . . . ?
C2 C3 C4 C5 0.3(9) . . . . ?
C6 C5 C4 C3 -1.5(8) . . . . ?
C7 C5 C4 C3 176.6(5) . . . . ?
Cu1 O1 C22 O2 171.1(4) . . . . ?
Cu1 O1 C22 C2 -7.4(9) . . . . ?
C3 C2 C22 O2 1.0(8) . . . . ?
C1 C2 C22 O2 -177.0(5) . . . . ?
C3 C2 C22 O1 179.5(5) . . . . ?
C1 C2 C22 O1 1.5(8) . . . . ?
C17 N5 C21 C20 0.4(9) . . . . ?
Cu1 N5 C21 C20 176.8(4) . . . . ?
N5 C21 C20 C19 -1.5(9) . . . . ?
Cu2 O3 C7 O4 -5.7(5) . . . . ?
Cu2 O3 C7 C5 173.2(5) . . . . ?
Cu2 O4 C7 O3 6.6(6) . . . . ?
Cu2 O4 C7 C5 -172.3(4) . . . . ?
C6 C5 C7 O3 5.6(8) . . . . ?
C4 C5 C7 O3 -172.6(5) . . . . ?
C6 C5 C7 O4 -175.4(5) . . . . ?
C4 C5 C7 O4 6.4(7) . . . . ?
C6 C5 C7 Cu2 157.1(15) . . . . ?
C4 C5 C7 Cu2 -21(2) . . . . ?
C21 C20 C19 C18 2.9(10) . . . . ?
C12 N6 C8 C9 0.2(10) . . . . ?
Cu2 N6 C8 C9 -175.6(5) . . . . ?
C21 N5 C17 C18 -0.9(10) . . . . ?
Cu1 N5 C17 C18 -177.1(6) . . . . ?
C20 C19 C18 C17 -3.3(11) . . . . ?
N5 C17 C18 C19 2.3(12) . . . . ?
C8 N6 C12 C11 -0.2(11) . . . . ?
Cu2 N6 C12 C11 175.7(7) . . . . ?
N6 C8 C9 C10 -0.5(11) . . . . ?
C8 C9 C10 C11 0.9(13) . . . . ?
C9 C10 C11 C12 -0.9(15) . . . . ?
N6 C12 C11 C10 0.6(15) . . . . ?

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 H3N O2 0.86 2.14 2.996(5) 172.7 4_645 yes

_refine_diff_density_max         0.380
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.075



