# 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_compound1
_database_code_depnum_ccdc_archive 'CCDC 2219404'
loop_
_audit_author_name
_audit_author_address
'Jaursup Boonmak'
;Khon Kaen University
Thailand
;
_audit_update_record             
;
2023-04-18 deposited with the CCDC.	2023-04-18 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT934_compound1           
;
PROBLEM: Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          2 Check
RESPONSE: The diffraction data of 1 is poor due to its very small size of single crystal. 
;
# Added during the CSD deposition process: Tuesday 18 April 2023 06:59 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H16 Cu2 N8 O10'
_chemical_formula_weight         607.45

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      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                   7.786(4)
_cell_length_b                   11.835(5)
_cell_length_c                   12.180(6)
_cell_angle_alpha                69.541(14)
_cell_angle_beta                 85.096(16)
_cell_angle_gamma                88.432(15)
_cell_volume                     1047.7(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3644
_cell_measurement_theta_min      2.9795
_cell_measurement_theta_max      23.4425

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.926
_exptl_crystal_F_000             612
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    2.107
_shelx_estimated_absorpt_T_min   0.902
_shelx_estimated_absorpt_T_max   0.939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6750
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   SADABS-2014/5
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  
;
Bruker D8 QUEST PHOTON 100
;
_diffrn_measurement_method       '\fandω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33336
_diffrn_reflns_av_unetI/netI     0.0922
_diffrn_reflns_av_R_equivalents  0.1526
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.979
_diffrn_reflns_theta_max         25.324
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3829
_reflns_number_gt                2457
_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       BrukerAPEX2
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    SHELXL
_computing_publication_material  SHELXL
_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)+(0.0571P)²+13.8672P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3829
_refine_ls_number_parameters     331
_refine_ls_number_restraints     265
_refine_ls_R_factor_all          0.1293
_refine_ls_R_factor_gt           0.0722
_refine_ls_wR_factor_ref         0.2040
_refine_ls_wR_factor_gt          0.1835
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_restrained_S_all      1.123
_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 0.68440(15) 0.71681(10) 0.42422(10) 0.0209(4) Uani 1 1 d . . . . .
Cu2 Cu 0.41309(16) 0.66925(10) 0.72834(10) 0.0214(4) Uani 1 1 d . . . . .
O1 O 0.8000(9) 0.5871(6) 0.3734(6) 0.0241(15) Uani 1 1 d . U . . .
O2 O 0.8619(9) 0.3915(6) 0.4333(6) 0.0289(17) Uani 1 1 d . U . . .
O3 O 0.3811(9) 0.5119(6) 0.8650(5) 0.0235(15) Uani 1 1 d . U . . .
O4 O 0.4548(10) 0.3173(6) 0.9261(6) 0.0328(17) Uani 1 1 d . U . . .
O5 O 0.6512(9) 0.8477(6) 0.2707(6) 0.0257(16) Uani 1 1 d . U . . .
O6 O 0.5183(9) 1.0230(6) 0.1899(6) 0.0323(17) Uani 1 1 d . U . . .
O7 O 0.2059(9) 0.7678(6) 0.7560(6) 0.0258(15) Uani 1 1 d . U . . .
O8 O 0.0664(9) 0.9380(7) 0.6685(6) 0.0334(18) Uani 1 1 d . U . . .
O9 O 0.9363(10) 0.7985(7) 0.4319(8) 0.053(2) Uani 1 1 d . . . . .
H1 H 1.0031 0.7566 0.4851 0.079 Uiso 1 1 d R U . . .
H2 H 0.9329 0.8687 0.4395 0.079 Uiso 1 1 d R U . . .
O10 O 0.5776(9) 0.7469(6) 0.8303(6) 0.0301(17) Uani 1 1 d . . . . .
H4 H 0.5473 0.8192 0.8209 0.045 Uiso 1 1 d R U . . .
H5 H 0.5565 0.7095 0.9049 0.045 Uiso 1 1 d R U . . .
N1 N 0.6562(10) 0.5817(7) 0.5707(7) 0.0213(17) Uani 1 1 d . U . . .
N2 N 0.5671(10) 0.5657(7) 0.6734(7) 0.0203(16) Uani 1 1 d . U . . .
N3 N 0.5184(10) 0.8143(6) 0.4781(6) 0.0182(16) Uani 1 1 d . U . . .
N4 N 0.4242(10) 0.7980(7) 0.5787(7) 0.0190(16) Uani 1 1 d . U . . .
N5 N 0.7309(15) -0.0187(13) 1.0042(11) 0.059(3) Uani 1 1 d D U . . .
N6 N 0.8896(12) -0.0295(9) 0.8581(8) 0.038(2) Uani 1 1 d . U . . .
H6 H 0.9487 -0.0578 0.8106 0.045 Uiso 1 1 calc R U . . .
N7 N 0.0210(11) 0.4925(8) 0.2119(7) 0.0279(18) Uani 1 1 d . U . . .
H7 H -0.0302 0.4598 0.2810 0.034 Uiso 1 1 calc R U . . .
N8 N 0.1814(11) 0.5165(9) 0.0540(7) 0.0319(19) Uani 1 1 d . U . . .
H8A H 0.2518 0.5023 0.0020 0.038 Uiso 1 1 calc R U . . .
C1 C 0.7976(12) 0.4820(9) 0.4515(8) 0.0200(18) Uani 1 1 d . U . . .
C2 C 0.7096(12) 0.4731(8) 0.5672(8) 0.0199(18) Uani 1 1 d . U . . .
C3 C 0.6519(12) 0.3831(9) 0.6731(8) 0.0215(19) Uani 1 1 d . U . . .
H3 H 0.6691 0.3003 0.6952 0.026 Uiso 1 1 calc R U . . .
C4 C 0.5641(12) 0.4452(8) 0.7367(8) 0.0170(17) Uani 1 1 d . U . . .
C5 C 0.4596(12) 0.4192(8) 0.8506(8) 0.0203(19) Uani 1 1 d . U . . .
C6 C 0.5456(13) 0.9312(9) 0.2748(8) 0.0219(19) Uani 1 1 d . U . . .
C7 C 0.4558(12) 0.9099(8) 0.3938(8) 0.0189(17) Uani 1 1 d . U . . .
C8 C 0.3142(13) 0.9578(8) 0.4428(8) 0.0207(19) Uani 1 1 d . U . . .
H8 H 0.2460 1.0238 0.4061 0.025 Uiso 1 1 calc R U . . .
C9 C 0.3017(13) 0.8809(8) 0.5614(8) 0.0208(18) Uani 1 1 d . U . . .
C10 C 0.1819(12) 0.8634(9) 0.6678(8) 0.0203(19) Uani 1 1 d . U . . .
C11 C 0.8068(16) -0.0961(13) 0.9575(11) 0.052(3) Uani 1 1 d . U . . .
H11 H 0.8020 -0.1798 0.9889 0.062 Uiso 1 1 calc R U . . .
C12 C 0.8694(15) 0.0899(11) 0.8404(11) 0.044(2) Uani 1 1 d . U . . .
H12 H 0.9145 0.1551 0.7772 0.052 Uiso 1 1 calc R U . . .
C13 C 0.7684(17) 0.0923(14) 0.9359(12) 0.056(3) Uani 1 1 d . U . . .
H13 H 0.7316 0.1615 0.9506 0.067 Uiso 1 1 calc R U . . .
C14 C 0.1266(13) 0.4360(10) 0.1577(9) 0.030(2) Uani 1 1 d . U . . .
H14 H 0.1571 0.3550 0.1866 0.036 Uiso 1 1 calc R U . . .
C15 C 0.1094(14) 0.6223(11) 0.0440(9) 0.033(2) Uani 1 1 d . U . . .
H15 H 0.1274 0.6934 -0.0200 0.040 Uiso 1 1 calc R U . . .
C16 C 0.0051(14) 0.6093(10) 0.1427(9) 0.033(2) Uani 1 1 d . U . . .
H16 H -0.0627 0.6681 0.1593 0.040 Uiso 1 1 calc R U . . .
H5A H 0.69(4) -0.06(2) 1.079(9) 0.26(15) Uiso 1 1 d 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 N3 1.933(7) . ?
Cu1 N1 1.936(8) . ?
Cu1 O5 2.000(7) . ?
Cu1 O1 2.011(6) . ?
Cu1 O9 2.233(8) . ?
Cu2 N4 1.920(8) . ?
Cu2 N2 1.935(8) . ?
Cu2 O3 2.022(6) . ?
Cu2 O7 2.038(7) . ?
Cu2 O10 2.272(7) . ?
O1 C1 1.275(11) . ?
O2 C1 1.251(11) . ?
O3 C5 1.299(11) . ?
O4 C5 1.234(11) . ?
O5 C6 1.280(11) . ?
O6 C6 1.238(11) . ?
O7 C10 1.282(11) . ?
O8 C10 1.244(11) . ?
O9 H1 0.8693 . ?
O9 H2 0.8674 . ?
O10 H4 0.8522 . ?
O10 H5 0.8629 . ?
N1 N2 1.332(10) . ?
N1 C2 1.354(12) . ?
N2 C4 1.363(12) . ?
N3 N4 1.329(10) . ?
N3 C7 1.348(12) . ?
N4 C9 1.325(12) . ?
N5 C13 1.310(19) . ?
N5 C11 1.338(18) . ?
N5 H5A 0.900(11) . ?
N6 C11 1.315(15) . ?
N6 C12 1.360(15) . ?
N6 H6 0.8600 . ?
N7 C14 1.322(12) . ?
N7 C16 1.353(14) . ?
N7 H7 0.8600 . ?
N8 C15 1.328(14) . ?
N8 C14 1.332(13) . ?
N8 H8A 0.8600 . ?
C1 C2 1.484(13) . ?
C2 C3 1.402(13) . ?
C3 C4 1.374(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.484(12) . ?
C6 C7 1.495(13) . ?
C7 C8 1.409(13) . ?
C8 C9 1.409(13) . ?
C8 H8 0.9300 . ?
C9 C10 1.486(13) . ?
C11 H11 0.9300 . ?
C12 C13 1.355(17) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.356(14) . ?
C15 H15 0.9300 . ?
C16 H16 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
N3 Cu1 N1 93.0(3) . . ?
N3 Cu1 O5 80.7(3) . . ?
N1 Cu1 O5 165.6(3) . . ?
N3 Cu1 O1 164.3(3) . . ?
N1 Cu1 O1 80.2(3) . . ?
O5 Cu1 O1 102.4(3) . . ?
N3 Cu1 O9 103.0(3) . . ?
N1 Cu1 O9 104.1(3) . . ?
O5 Cu1 O9 90.0(3) . . ?
O1 Cu1 O9 92.4(3) . . ?
N4 Cu2 N2 94.1(3) . . ?
N4 Cu2 O3 167.0(3) . . ?
N2 Cu2 O3 79.3(3) . . ?
N4 Cu2 O7 80.4(3) . . ?
N2 Cu2 O7 163.8(3) . . ?
O3 Cu2 O7 102.8(3) . . ?
N4 Cu2 O10 100.7(3) . . ?
N2 Cu2 O10 104.8(3) . . ?
O3 Cu2 O10 91.9(3) . . ?
O7 Cu2 O10 91.2(3) . . ?
C1 O1 Cu1 115.6(6) . . ?
C5 O3 Cu2 115.7(6) . . ?
C6 O5 Cu1 116.0(6) . . ?
C10 O7 Cu2 113.5(6) . . ?
Cu1 O9 H1 117.7 . . ?
Cu1 O9 H2 117.0 . . ?
H1 O9 H2 103.7 . . ?
Cu2 O10 H4 110.0 . . ?
Cu2 O10 H5 110.1 . . ?
H4 O10 H5 103.6 . . ?
N2 N1 C2 109.0(7) . . ?
N2 N1 Cu1 133.4(6) . . ?
C2 N1 Cu1 116.4(6) . . ?
N1 N2 C4 107.8(7) . . ?
N1 N2 Cu2 132.5(6) . . ?
C4 N2 Cu2 118.1(6) . . ?
N4 N3 C7 108.6(7) . . ?
N4 N3 Cu1 134.1(6) . . ?
C7 N3 Cu1 115.9(6) . . ?
C9 N4 N3 109.4(7) . . ?
C9 N4 Cu2 117.4(6) . . ?
N3 N4 Cu2 132.4(6) . . ?
C13 N5 C11 109.8(12) . . ?
C13 N5 H5A 140(10) . . ?
C11 N5 H5A 107(10) . . ?
C11 N6 C12 111.0(11) . . ?
C11 N6 H6 124.5 . . ?
C12 N6 H6 124.5 . . ?
C14 N7 C16 109.9(9) . . ?
C14 N7 H7 125.0 . . ?
C16 N7 H7 125.0 . . ?
C15 N8 C14 108.8(9) . . ?
C15 N8 H8A 125.6 . . ?
C14 N8 H8A 125.6 . . ?
O2 C1 O1 123.3(8) . . ?
O2 C1 C2 121.5(8) . . ?
O1 C1 C2 115.1(8) . . ?
N1 C2 C3 108.9(8) . . ?
N1 C2 C1 112.4(8) . . ?
C3 C2 C1 138.4(9) . . ?
C4 C3 C2 104.2(8) . . ?
C4 C3 H3 127.9 . . ?
C2 C3 H3 127.9 . . ?
N2 C4 C3 110.1(8) . . ?
N2 C4 C5 111.1(8) . . ?
C3 C4 C5 138.7(9) . . ?
O4 C5 O3 123.7(8) . . ?
O4 C5 C4 121.3(8) . . ?
O3 C5 C4 114.9(8) . . ?
O6 C6 O5 124.6(9) . . ?
O6 C6 C7 121.5(9) . . ?
O5 C6 C7 113.9(8) . . ?
N3 C7 C8 109.4(8) . . ?
N3 C7 C6 113.0(8) . . ?
C8 C7 C6 137.5(9) . . ?
C7 C8 C9 102.6(8) . . ?
C7 C8 H8 128.7 . . ?
C9 C8 H8 128.7 . . ?
N4 C9 C8 110.0(8) . . ?
N4 C9 C10 112.8(8) . . ?
C8 C9 C10 137.0(9) . . ?
O8 C10 O7 123.5(8) . . ?
O8 C10 C9 120.9(9) . . ?
O7 C10 C9 115.7(8) . . ?
N6 C11 N5 105.9(13) . . ?
N6 C11 H11 127.0 . . ?
N5 C11 H11 127.0 . . ?
C13 C12 N6 104.3(12) . . ?
C13 C12 H12 127.9 . . ?
N6 C12 H12 127.9 . . ?
N5 C13 C12 109.0(12) . . ?
N5 C13 H13 125.5 . . ?
C12 C13 H13 125.5 . . ?
N7 C14 N8 107.3(10) . . ?
N7 C14 H14 126.4 . . ?
N8 C14 H14 126.4 . . ?
N8 C15 C16 108.6(10) . . ?
N8 C15 H15 125.7 . . ?
C16 C15 H15 125.7 . . ?
N7 C16 C15 105.3(10) . . ?
N7 C16 H16 127.4 . . ?
C15 C16 H16 127.4 . . ?

_refine_diff_density_max         1.122
_refine_diff_density_min         -0.805
_refine_diff_density_rms         0.203

####################################################################### 
# 
# 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_compound2
_database_code_depnum_ccdc_archive 'CCDC 2219405'
loop_
_audit_author_name
_audit_author_address
'Jaursup Boonmak'
;Khon Kaen University
Thailand
;
_audit_update_record             
;
2023-04-18 deposited with the CCDC.	2023-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 Cu3 N8 O12'
_chemical_formula_weight         705.00

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                   5.3873(7)
_cell_length_b                   6.9457(8)
_cell_length_c                   15.7187(19)
_cell_angle_alpha                90.039(4)
_cell_angle_beta                 90.275(4)
_cell_angle_gamma                108.287(4)
_cell_volume                     558.46(12)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5561
_cell_measurement_theta_min      3.089
_cell_measurement_theta_max      26.3265

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.096
_exptl_crystal_F_000             353
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    2.916
_shelx_estimated_absorpt_T_min   0.868
_shelx_estimated_absorpt_T_max   0.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6659
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS-2014/5
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  
;
Bruker D8 QUEST PHOTON 100
;
_diffrn_measurement_method       '\fandω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14849
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.347
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2203
_reflns_number_gt                1725
_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       BrukerAPEX2
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    SHELXL
_computing_publication_material  SHELXL
_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)+(0.0316P)²+0.3675P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2203
_refine_ls_number_parameters     225
_refine_ls_number_restraints     155
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0282
_refine_ls_wR_factor_ref         0.0656
_refine_ls_wR_factor_gt          0.0602
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 1.0000 0.5000 0.5000 0.02081(14) Uani 1 2 d S . P A 1
Cu2 Cu 0.84041(7) 0.60203(6) 0.77538(2) 0.02355(13) Uani 1 1 d D . . A 1
O1 O 0.7395(4) 0.3132(3) 0.43076(12) 0.0281(5) Uani 1 1 d . U . A 1
O2 O 0.3238(4) 0.1123(3) 0.42806(12) 0.0278(5) Uani 1 1 d . U . A 1
O3 O 0.5082(4) 0.4454(4) 0.82766(12) 0.0362(6) Uani 1 1 d . U . A 1
O4 O 0.1150(5) 0.2315(4) 0.79947(14) 0.0524(8) Uani 1 1 d . U . A 1
O5 O 1.1754(4) 0.7329(4) 0.72561(13) 0.0467(7) Uani 1 1 d . . . A 1
H1 H 1.2113 0.7222 0.6736 0.070 Uiso 1 1 d R U . A 1
H2 H 1.3230 0.7859 0.7494 0.070 Uiso 1 1 d R U . A 1
O6 O 0.7059(4) 0.8965(3) 0.74552(13) 0.0320(5) Uani 1 1 d . . . A 1
H5 H 0.6901 0.9073 0.6921 0.048 Uiso 1 1 d R U . A 1
H9 H 0.8280 1.0030 0.7597 0.048 Uiso 1 1 d R U . A 1
N1 N 0.7211(4) 0.4149(3) 0.58873(13) 0.0184(5) Uani 1 1 d . U . A 1
N2 N 0.6750(4) 0.4430(4) 0.67190(14) 0.0201(5) Uani 1 1 d . U . A 1
N3 N 0.975(2) 0.715(6) 0.8889(10) 0.020(3) Uani 0.5 1 d D U P A 1
N4 N 0.976(3) 0.770(3) 1.0267(9) 0.025(3) Uani 0.5 1 d D U P A 1
H4 H 0.9145 0.7853 1.0757 0.030 Uiso 0.5 1 calc R U P A 1
C1 C 0.5127(5) 0.2264(4) 0.46562(17) 0.0199(6) Uani 1 1 d . U . A 1
C2 C 0.5033(5) 0.2808(4) 0.55595(17) 0.0184(6) Uani 1 1 d . U . A 1
C3 C 0.3105(6) 0.2189(4) 0.61675(17) 0.0226(6) Uani 1 1 d . U . A 1
H3 H 0.1427 0.1281 0.6109 0.027 Uiso 1 1 calc R U . A 1
C4 C 0.4276(6) 0.3246(4) 0.68848(17) 0.0229(6) Uani 1 1 d . U . A 1
C5 C 0.3385(6) 0.3311(5) 0.77711(18) 0.0314(8) Uani 1 1 d . U . A 1
C6 C 1.2164(15) 0.8276(12) 0.9169(5) 0.0268(18) Uani 0.5 1 d D U P A 1
H6 H 1.3601 0.8827 0.8820 0.032 Uiso 0.5 1 calc R U P A 1
C7 C 1.2178(19) 0.8485(13) 1.0022(5) 0.029(2) Uani 0.5 1 d D U P A 1
H7 H 1.3625 0.9073 1.0367 0.035 Uiso 0.5 1 calc R U P A 1
C8 C 0.838(2) 0.657(2) 0.9600(8) 0.023(3) Uani 0.5 1 d D U P A 1
H8 H 0.6760 0.5576 0.9638 0.027 Uiso 0.5 1 calc R U P A 1
N3A N 0.966(2) 0.690(5) 0.8922(9) 0.020(4) Uani 0.5 1 d D . P B 2
N4A N 0.967(2) 0.726(3) 1.0293(9) 0.023(3) Uani 0.5 1 d D . P B 2
H4A H 0.9073 0.7098 1.0803 0.027 Uiso 0.5 1 calc R U P B 2
C6A C 1.2151(16) 0.7326(12) 0.9229(5) 0.028(2) Uani 0.5 1 d D U P B 2
H6A H 1.3622 0.7391 0.8909 0.033 Uiso 0.5 1 calc R U P B 2
C7A C 1.2114(19) 0.7637(12) 1.0075(6) 0.028(2) Uani 0.5 1 d D U P B 2
H7A H 1.3559 0.8043 1.0436 0.033 Uiso 0.5 1 calc R U P B 2
C8A C 0.825(3) 0.718(2) 0.9567(9) 0.036(4) Uani 0.5 1 d D . P B 2
H8A H 0.6574 0.7291 0.9531 0.044 Uiso 0.5 1 calc R U P B 2


_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 1.9177(19) . ?
Cu1 O1 1.9177(19) 2_766 ?
Cu1 N1 2.004(2) . ?
Cu1 N1 2.004(2) 2_766 ?
Cu2 O5 1.918(2) . ?
Cu2 O3 1.963(2) . ?
Cu2 N3 1.989(15) . ?
Cu2 N2 2.007(2) . ?
Cu2 O6 2.420(2) . ?
O1 C1 1.305(3) . ?
O2 C1 1.224(3) . ?
O3 C5 1.278(4) . ?
O4 C5 1.238(4) . ?
O5 H1 0.8504 . ?
O5 H2 0.8496 . ?
O6 H5 0.8499 . ?
O6 H9 0.8503 . ?
N1 C2 1.348(4) . ?
N1 N2 1.357(3) . ?
N2 C4 1.355(4) . ?
N3 C8 1.334(15) . ?
N3 C6 1.359(13) . ?
N4 C7 1.304(11) . ?
N4 C8 1.375(13) . ?
N4 H4 0.8600 . ?
C1 C2 1.474(4) . ?
C2 C3 1.381(4) . ?
C3 C4 1.382(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.481(4) . ?
C6 C7 1.349(9) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
N3A C8A 1.321(15) . ?
N3A C6A 1.364(13) . ?
N4A C7A 1.305(11) . ?
N4A C8A 1.365(14) . ?
N4A H4A 0.8600 . ?
C6A C7A 1.348(9) . ?
C6A H6A 0.9300 . ?
C7A H7A 0.9300 . ?
C8A H8A 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 O1 180.00(9) . 2_766 ?
O1 Cu1 N1 82.71(8) . . ?
O1 Cu1 N1 97.29(8) 2_766 . ?
O1 Cu1 N1 97.29(8) . 2_766 ?
O1 Cu1 N1 82.71(9) 2_766 2_766 ?
N1 Cu1 N1 180.00(9) . 2_766 ?
O5 Cu2 O3 174.61(11) . . ?
O5 Cu2 N3 90.5(5) . . ?
O3 Cu2 N3 89.8(5) . . ?
O5 Cu2 N2 96.70(9) . . ?
O3 Cu2 N2 82.36(9) . . ?
N3 Cu2 N2 170.0(10) . . ?
O5 Cu2 O6 90.37(10) . . ?
O3 Cu2 O6 95.01(9) . . ?
N3 Cu2 O6 90.5(11) . . ?
N2 Cu2 O6 96.33(9) . . ?
C1 O1 Cu1 116.98(16) . . ?
C5 O3 Cu2 115.63(18) . . ?
Cu2 O5 H1 124.2 . . ?
Cu2 O5 H2 129.7 . . ?
H1 O5 H2 104.5 . . ?
Cu2 O6 H5 109.3 . . ?
Cu2 O6 H9 109.3 . . ?
H5 O6 H9 104.5 . . ?
C2 N1 N2 107.7(2) . . ?
C2 N1 Cu1 110.43(17) . . ?
N2 N1 Cu1 141.83(18) . . ?
C4 N2 N1 107.0(2) . . ?
C4 N2 Cu2 110.90(17) . . ?
N1 N2 Cu2 142.06(18) . . ?
C8 N3 C6 104.2(11) . . ?
C8 N3 Cu2 122.3(13) . . ?
C6 N3 Cu2 132.6(10) . . ?
C7 N4 C8 107.5(11) . . ?
C7 N4 H4 126.2 . . ?
C8 N4 H4 126.2 . . ?
O2 C1 O1 124.3(2) . . ?
O2 C1 C2 122.5(2) . . ?
O1 C1 C2 113.2(2) . . ?
N1 C2 C3 111.0(2) . . ?
N1 C2 C1 116.6(2) . . ?
C3 C2 C1 132.3(3) . . ?
C2 C3 C4 103.1(2) . . ?
C2 C3 H3 128.4 . . ?
C4 C3 H3 128.4 . . ?
N2 C4 C3 111.1(2) . . ?
N2 C4 C5 115.7(2) . . ?
C3 C4 C5 133.2(3) . . ?
O4 C5 O3 123.3(3) . . ?
O4 C5 C4 121.5(3) . . ?
O3 C5 C4 115.2(3) . . ?
C7 C6 N3 110.5(8) . . ?
C7 C6 H6 124.7 . . ?
N3 C6 H6 124.7 . . ?
N4 C7 C6 106.4(8) . . ?
N4 C7 H7 126.8 . . ?
C6 C7 H7 126.8 . . ?
N3 C8 N4 108.5(14) . . ?
N3 C8 H8 125.8 . . ?
N4 C8 H8 125.8 . . ?
C8A N3A C6A 105.9(11) . . ?
C7A N4A C8A 107.7(11) . . ?
C7A N4A H4A 126.2 . . ?
C8A N4A H4A 126.2 . . ?
C7A C6A N3A 108.4(9) . . ?
C7A C6A H6A 125.8 . . ?
N3A C6A H6A 125.8 . . ?
N4A C7A C6A 107.3(9) . . ?
N4A C7A H7A 126.4 . . ?
C6A C7A H7A 126.4 . . ?
N3A C8A N4A 107.7(14) . . ?
N3A C8A H8A 126.1 . . ?
N4A C8A H8A 126.1 . . ?

_refine_diff_density_max         0.427
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.087

####################################################################### 
# 
# 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_compound7
_database_code_depnum_ccdc_archive 'CCDC 2219409'
loop_
_audit_author_name
_audit_author_address
'Jaursup Boonmak'
;Khon Kaen University
Thailand
;
_audit_update_record             
;
2022-11-14 deposited with the CCDC.	2023-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            
{diaqua-bis(ethylenediamine)-bis(mu-pyrazole-3,5-dicarbarboxylato)tricopper(II)}
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H22 Cu3 N8 O10'
_chemical_formula_weight         653.01

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                   7.1285(2)
_cell_length_b                   8.7861(3)
_cell_length_c                   9.7390(4)
_cell_angle_alpha                114.0320(10)
_cell_angle_beta                 94.7760(10)
_cell_angle_gamma                101.9570(10)
_cell_volume                     535.33(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4342.5
_cell_measurement_theta_min      2.974
_cell_measurement_theta_max      27.375

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.026
_exptl_crystal_F_000             329
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    3.026
_shelx_estimated_absorpt_T_min   0.518
_shelx_estimated_absorpt_T_max   0.713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5744
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS-2014/5
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  
;
Bruker D8 QUEST PHOTON 100
;
_diffrn_measurement_method       '\fandω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18542
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_av_R_equivalents  0.0729
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.974
_diffrn_reflns_theta_max         27.514
_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             2456
_reflns_number_gt                2085
_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       BrukerAPEX2
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    SHELXL
_computing_publication_material  SHELXL
_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)+(0.0294P)²+0.5553P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2456
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0770
_refine_ls_wR_factor_gt          0.0731
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.77847(4) 0.45968(4) 0.70682(3) 0.01698(11) Uani 1 1 d . . . . .
Cu2 Cu 1.0000 0.0000 0.5000 0.01932(13) Uani 1 2 d S . P . .
O1 O 0.4972(3) 0.4421(2) 0.6507(2) 0.0240(4) Uani 1 1 d . . . . .
O2 O 0.2298(3) 0.2699(3) 0.4751(2) 0.0242(4) Uani 1 1 d . . . . .
O3 O 0.9117(3) -0.1534(2) 0.2774(2) 0.0229(4) Uani 1 1 d . . . . .
O4 O 0.6516(3) -0.2450(2) 0.0914(2) 0.0250(4) Uani 1 1 d . . . . .
O5 O 0.7310(3) 0.4395(3) 0.9326(2) 0.0261(4) Uani 1 1 d . . . . .
N1 N 0.7030(3) 0.2212(3) 0.5417(2) 0.0154(4) Uani 1 1 d . . . . .
N2 N 0.7906(3) 0.1004(3) 0.4625(2) 0.0159(4) Uani 1 1 d . . . . .
N3 N 0.8441(4) 0.7187(3) 0.8181(3) 0.0226(5) Uani 1 1 d . . . . .
N4 N 1.0649(3) 0.4932(3) 0.7408(3) 0.0216(5) Uani 1 1 d . . . . .
C1 C 0.4058(4) 0.3075(3) 0.5310(3) 0.0176(5) Uani 1 1 d . . . . .
C2 C 0.5261(3) 0.1865(3) 0.4576(3) 0.0155(5) Uani 1 1 d . . . . .
C3 C 0.4967(4) 0.0421(3) 0.3203(3) 0.0191(5) Uani 1 1 d . . . . .
H3 H 0.3882 -0.0094 0.2416 0.023 Uiso 1 1 calc R U . . .
C4 C 0.6685(4) -0.0080(3) 0.3282(3) 0.0164(5) Uani 1 1 d . . . . .
C5 C 0.7458(4) -0.1466(3) 0.2237(3) 0.0187(5) Uani 1 1 d . . . . .
C6 C 1.0524(4) 0.7854(3) 0.8921(3) 0.0272(6) Uani 1 1 d . . . . .
H6A H 1.0690 0.7788 0.9892 0.033 Uiso 1 1 calc R U . . .
H6B H 1.1001 0.9053 0.9111 0.033 Uiso 1 1 calc R U . . .
C7 C 1.1645(4) 0.6760(4) 0.7856(4) 0.0283(6) Uani 1 1 d . . . . .
H7A H 1.1669 0.6979 0.6957 0.034 Uiso 1 1 calc R U . . .
H7B H 1.2980 0.7034 0.8369 0.034 Uiso 1 1 calc R U . . .
H1 H 0.716(5) 0.528(5) 0.989(4) 0.029(9) Uiso 1 1 d . . . . .
H2 H 0.638(6) 0.371(6) 0.927(5) 0.053(13) Uiso 1 1 d . . . . .
H3A H 0.830(5) 0.752(5) 0.757(4) 0.033(10) Uiso 1 1 d . . . . .
H3B H 0.773(5) 0.755(5) 0.881(4) 0.037(10) Uiso 1 1 d . . . . .
H4A H 1.108(5) 0.431(5) 0.673(4) 0.031(9) Uiso 1 1 d . . . . .
H4B H 1.095(5) 0.467(5) 0.814(4) 0.034(10) 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 N1 1.977(2) . ?
Cu1 N4 1.981(2) . ?
Cu1 O1 1.9907(18) . ?
Cu1 N3 2.009(2) . ?
Cu1 O5 2.324(2) . ?
Cu2 N2 1.964(2) . ?
Cu2 N2 1.964(2) 2_756 ?
Cu2 O3 1.9883(18) . ?
Cu2 O3 1.9884(18) 2_756 ?
O1 C1 1.270(3) . ?
O2 C1 1.244(3) . ?
O3 C5 1.276(3) . ?
O4 C5 1.251(3) . ?
O5 H1 0.78(4) . ?
O5 H2 0.78(5) . ?
N1 N2 1.341(3) . ?
N1 C2 1.349(3) . ?
N2 C4 1.352(3) . ?
N3 C6 1.478(4) . ?
N3 H3A 0.77(4) . ?
N3 H3B 0.83(4) . ?
N4 C7 1.476(4) . ?
N4 H4A 0.80(4) . ?
N4 H4B 0.85(4) . ?
C1 C2 1.495(3) . ?
C2 C3 1.379(4) . ?
C3 C4 1.391(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.478(3) . ?
C6 C7 1.511(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?

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 N4 98.29(9) . . ?
N1 Cu1 O1 82.22(8) . . ?
N4 Cu1 O1 171.28(10) . . ?
N1 Cu1 N3 162.04(10) . . ?
N4 Cu1 N3 84.82(10) . . ?
O1 Cu1 N3 92.08(9) . . ?
N1 Cu1 O5 106.89(9) . . ?
N4 Cu1 O5 96.54(10) . . ?
O1 Cu1 O5 91.61(8) . . ?
N3 Cu1 O5 90.21(10) . . ?
N2 Cu2 N2 180.0 . 2_756 ?
N2 Cu2 O3 82.21(8) . . ?
N2 Cu2 O3 97.79(8) 2_756 . ?
N2 Cu2 O3 97.79(8) . 2_756 ?
N2 Cu2 O3 82.21(8) 2_756 2_756 ?
O3 Cu2 O3 180.0 . 2_756 ?
C1 O1 Cu1 114.61(15) . . ?
C5 O3 Cu2 113.23(16) . . ?
Cu1 O5 H1 107(3) . . ?
Cu1 O5 H2 116(3) . . ?
H1 O5 H2 104(4) . . ?
N2 N1 C2 107.96(19) . . ?
N2 N1 Cu1 138.20(16) . . ?
C2 N1 Cu1 110.82(15) . . ?
N1 N2 C4 107.85(19) . . ?
N1 N2 Cu2 138.95(16) . . ?
C4 N2 Cu2 110.74(16) . . ?
C6 N3 Cu1 108.95(17) . . ?
C6 N3 H3A 108(3) . . ?
Cu1 N3 H3A 107(3) . . ?
C6 N3 H3B 111(2) . . ?
Cu1 N3 H3B 114(3) . . ?
H3A N3 H3B 108(4) . . ?
C7 N4 Cu1 109.63(17) . . ?
C7 N4 H4A 110(2) . . ?
Cu1 N4 H4A 117(2) . . ?
C7 N4 H4B 110(2) . . ?
Cu1 N4 H4B 107(2) . . ?
H4A N4 H4B 102(3) . . ?
O2 C1 O1 125.6(2) . . ?
O2 C1 C2 119.7(2) . . ?
O1 C1 C2 114.7(2) . . ?
N1 C2 C3 110.7(2) . . ?
N1 C2 C1 115.1(2) . . ?
C3 C2 C1 134.2(2) . . ?
C2 C3 C4 103.3(2) . . ?
C2 C3 H3 128.4 . . ?
C4 C3 H3 128.4 . . ?
N2 C4 C3 110.2(2) . . ?
N2 C4 C5 115.0(2) . . ?
C3 C4 C5 134.7(2) . . ?
O4 C5 O3 124.5(2) . . ?
O4 C5 C4 120.1(2) . . ?
O3 C5 C4 115.3(2) . . ?
N3 C6 C7 107.8(2) . . ?
N3 C6 H6A 110.1 . . ?
C7 C6 H6A 110.1 . . ?
N3 C6 H6B 110.1 . . ?
C7 C6 H6B 110.1 . . ?
H6A C6 H6B 108.5 . . ?
N4 C7 C6 107.5(2) . . ?
N4 C7 H7A 110.2 . . ?
C6 C7 H7A 110.2 . . ?
N4 C7 H7B 110.2 . . ?
C6 C7 H7B 110.2 . . ?
H7A C7 H7B 108.5 . . ?

_refine_diff_density_max         0.555
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.096

####################################################################### 
# 
# 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_compound3
_database_code_depnum_ccdc_archive 'CCDC 2219415'
loop_
_audit_author_name
_audit_author_address
'Kittipong Chainok'
;Thammasat University
Thailand
;
_audit_update_record             
;
2023-04-18 deposited with the CCDC.	2023-04-18 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT934_compound3           
;
PROBLEM: Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          2 Check
RESPONSE: There are sixteen disordered lattice water molecules in compound 3. The disordered lattice water molecules were removed from diffraction data using the SQUEEZE routine of PLATON software. 
;
# Added during the CSD deposition process: Tuesday 18 April 2023 07:04 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H20 Cu4 N16 Na4 O18'
_chemical_formula_weight         1262.76

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'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   11.90320(10)
_cell_length_b                   11.90320(10)
_cell_length_c                   41.3061(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5852.50(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9913
_cell_measurement_theta_min      2.6135
_cell_measurement_theta_max      26.8285

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_F_000             2512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    1.535
_shelx_estimated_absorpt_T_min   0.790
_shelx_estimated_absorpt_T_max   1.550
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5645
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed x-ray tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3109
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_theta_min         3.122
_diffrn_reflns_theta_max         26.730
_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             3109
_reflns_number_gt                2466
_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       BrukerAPEX2
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    SHELXL
_computing_publication_material  SHELXL
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1093P)²+17.2151P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3109
_refine_ls_number_parameters     177
_refine_ls_number_restraints     136
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0588
_refine_ls_wR_factor_ref         0.1926
_refine_ls_wR_factor_gt          0.1846
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.078
_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 0.57695(5) 0.39562(4) 0.41276(2) 0.0350(2) Uani 1 1 d . . . A 1
Na1 Na 0.8889(7) 0.2051(10) 0.5126(2) 0.151(4) Uani 0.5 1 d . U P A 1
Na1A Na 0.7795(8) 0.0421(9) 0.5165(3) 0.163(5) Uani 0.5 1 d . . P B 2
O1 O 0.6076(3) 0.3640(3) 0.45965(8) 0.0536(10) Uani 1 1 d . U . A 1
O2 O 0.6988(4) 0.2461(4) 0.49183(9) 0.0756(14) Uani 1 1 d . U . A 1
O3 O 0.7592(3) 0.0105(3) 0.34634(9) 0.0525(9) Uani 1 1 d . U . A 1
O4 O 0.8796(4) -0.0420(4) 0.38488(13) 0.0756(13) Uani 1 1 d . U . A 1
O5 O 1.0000 0.2500 0.4637(3) 0.129(3) Uani 1 2 d S TU P A 1
N1 N 0.6457(3) 0.2456(3) 0.40811(8) 0.0341(8) Uani 1 1 d . U . A 1
N2 N 0.6807(3) 0.1786(3) 0.38398(9) 0.0331(7) Uani 1 1 d . U . A 1
N3 N 0.4834(3) 0.5252(3) 0.42462(9) 0.0382(8) Uani 1 1 d . U . A 1
N4 N 0.3902(4) 0.6455(4) 0.45391(11) 0.0551(11) Uani 1 1 d . U . A 1
H4 H 0.3623 0.6778 0.4707 0.066 Uiso 1 1 calc R U . A 1
C1 C 0.6656(5) 0.2762(5) 0.46484(11) 0.0515(12) Uani 1 1 d . U . A 1
C2 C 0.6941(4) 0.2103(4) 0.43564(11) 0.0380(9) Uani 1 1 d . U . A 1
C3 C 0.7625(4) 0.1188(4) 0.42943(12) 0.0409(10) Uani 1 1 d . U . A 1
H3 H 0.8062 0.0783 0.4440 0.049 Uiso 1 1 calc R U . A 1
C4 C 0.7508(4) 0.1018(4) 0.39656(11) 0.0367(9) Uani 1 1 d . U . A 1
C5 C 0.8001(4) 0.0170(4) 0.37421(14) 0.0488(11) Uani 1 1 d . U . A 1
C6 C 0.4531(4) 0.5532(5) 0.45371(12) 0.0480(11) Uani 1 1 d . U . A 1
H6 H 0.4730 0.5134 0.4722 0.058 Uiso 1 1 calc R U . A 1
C7 C 0.3783(5) 0.6789(5) 0.42300(14) 0.0529(12) Uani 1 1 d . U . A 1
H7 H 0.3393 0.7417 0.4157 0.063 Uiso 1 1 calc R U . A 1
C8 C 0.4343(4) 0.6032(4) 0.40457(14) 0.0469(11) Uani 1 1 d . U . A 1
H8 H 0.4388 0.6038 0.3821 0.056 Uiso 1 1 calc R U . A 1


_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 N3 1.965(4) . ?
Cu1 N1 1.974(4) . ?
Cu1 N2 1.976(4) 16_656 ?
Cu1 O1 2.007(3) . ?
Cu1 O3 2.390(4) 16_656 ?
Na1 O2 2.468(9) . ?
Na1 O5 2.472(13) . ?
Na1 Na1 2.85(2) 6_654 ?
O1 C1 1.269(6) . ?
O2 C1 1.237(6) . ?
O3 C5 1.252(7) . ?
O3 Cu1 2.389(4) 11_666 ?
O4 C5 1.258(7) . ?
O5 Na1 2.472(13) 6_654 ?
N1 C2 1.342(5) . ?
N1 N2 1.343(5) . ?
N2 C4 1.343(6) . ?
N2 Cu1 1.976(4) 11_666 ?
N3 C6 1.298(6) . ?
N3 C8 1.374(6) . ?
N4 C6 1.329(7) . ?
N4 C7 1.345(7) . ?
N4 H4 0.8600 . ?
C1 C2 1.479(6) . ?
C2 C3 1.384(6) . ?
C3 C4 1.380(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.489(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.356(7) . ?
C7 H7 0.9300 . ?
C8 H8 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
N3 Cu1 N1 165.85(17) . . ?
N3 Cu1 N2 93.38(16) . 16_656 ?
N1 Cu1 N2 96.30(15) . 16_656 ?
N3 Cu1 O1 90.58(15) . . ?
N1 Cu1 O1 81.28(14) . . ?
N2 Cu1 O1 171.35(16) 16_656 . ?
N3 Cu1 O3 93.10(15) . 16_656 ?
N1 Cu1 O3 99.26(15) . 16_656 ?
N2 Cu1 O3 75.77(13) 16_656 16_656 ?
O1 Cu1 O3 96.35(16) . 16_656 ?
O2 Na1 O5 99.4(3) . . ?
O2 Na1 Na1 140.9(6) . 6_654 ?
O5 Na1 Na1 54.8(3) . 6_654 ?
C1 O1 Cu1 114.6(3) . . ?
C1 O2 Na1 131.6(5) . . ?
C5 O3 Cu1 108.3(3) . 11_666 ?
Na1 O5 Na1 70.5(6) . 6_654 ?
C2 N1 N2 108.0(4) . . ?
C2 N1 Cu1 112.3(3) . . ?
N2 N1 Cu1 137.6(3) . . ?
N1 N2 C4 108.1(4) . . ?
N1 N2 Cu1 132.8(3) . 11_666 ?
C4 N2 Cu1 119.1(3) . 11_666 ?
C6 N3 C8 105.5(4) . . ?
C6 N3 Cu1 126.1(3) . . ?
C8 N3 Cu1 128.4(3) . . ?
C6 N4 C7 107.3(4) . . ?
C6 N4 H4 126.3 . . ?
C7 N4 H4 126.3 . . ?
O2 C1 O1 124.4(5) . . ?
O2 C1 C2 120.5(4) . . ?
O1 C1 C2 115.1(4) . . ?
N1 C2 C3 110.0(4) . . ?
N1 C2 C1 115.2(4) . . ?
C3 C2 C1 134.8(4) . . ?
C4 C3 C2 103.8(4) . . ?
C4 C3 H3 128.1 . . ?
C2 C3 H3 128.1 . . ?
N2 C4 C3 110.1(4) . . ?
N2 C4 C5 117.8(4) . . ?
C3 C4 C5 132.1(4) . . ?
O3 C5 O4 125.5(5) . . ?
O3 C5 C4 117.3(5) . . ?
O4 C5 C4 117.2(5) . . ?
N3 C6 N4 112.0(4) . . ?
N3 C6 H6 124.0 . . ?
N4 C6 H6 124.0 . . ?
N4 C7 C8 106.5(5) . . ?
N4 C7 H7 126.7 . . ?
C8 C7 H7 126.7 . . ?
C7 C8 N3 108.7(5) . . ?
C7 C8 H8 125.7 . . ?
N3 C8 H8 125.7 . . ?

_refine_diff_density_max         1.107
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.108


_exptl_crystal_preparation       'Magnetic properties'
####################################################################### 
# 
# 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_compound6
_database_code_depnum_ccdc_archive 'CCDC 2219408'
loop_
_audit_author_name
_audit_author_address
'Jaursup Boonmak'
;Khon Kaen University
Thailand
;
_audit_update_record             
;
2023-04-18 deposited with the CCDC.	2023-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H14 Cu3 N4 O14'
_chemical_formula_weight         604.87

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

_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                   5.1649(2)
_cell_length_b                   6.8991(3)
_cell_length_c                   12.5680(5)
_cell_angle_alpha                96.615(2)
_cell_angle_beta                 94.583(2)
_cell_angle_gamma                102.134(2)
_cell_volume                     432.41(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3534
_cell_measurement_theta_min      3.0485
_cell_measurement_theta_max      26.842

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.323
_exptl_crystal_F_000             301
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    3.746
_shelx_estimated_absorpt_T_min   0.754
_shelx_estimated_absorpt_T_max   0.929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4569
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS-2014/5
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  
;
Bruker D8 QUEST PHOTON 100
;
_diffrn_measurement_method       '\fandω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12041
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_av_R_equivalents  0.0897
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.261
_diffrn_reflns_theta_max         27.095
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1905
_reflns_number_gt                1472
_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       BrukerAPEX2
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    SHELXL
_computing_publication_material  SHELXL
_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)+(0.0318P)²+0.6929P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1905
_refine_ls_number_parameters     143
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.0974
_refine_ls_wR_factor_gt          0.0895
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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 0.14035(9) 0.09659(7) 0.65107(4) 0.01765(17) Uani 1 1 d . . . . .
Cu2 Cu 1.0000 0.5000 1.0000 0.0229(2) Uani 1 2 d S . P . .
O1 O 0.4966(5) 0.2704(4) 0.7057(2) 0.0218(6) Uani 1 1 d . . . . .
O2 O 0.8899(5) 0.4017(4) 0.6534(2) 0.0254(7) Uani 1 1 d . . . . .
O3 O 0.0244(5) -0.0168(4) 0.2173(2) 0.0207(6) Uani 1 1 d . . . . .
O4 O 0.3854(6) 0.1661(4) 0.1627(2) 0.0259(7) Uani 1 1 d . . . . .
O5 O 0.6553(5) 0.3510(5) 0.9169(2) 0.0327(8) Uani 1 1 d G . . . .
H1 H 0.6183 0.3303 0.8487 0.049 Uiso 1 1 d G U . . .
H2 H 0.5035 0.3390 0.9410 0.049 Uiso 1 1 d G U . . .
O6 O 1.1308(5) 0.5741(4) 0.8565(2) 0.0299(7) Uani 1 1 d G . . . .
H4 H 1.0581 0.5219 0.7937 0.045 Uiso 1 1 d G U . . .
H5 H 1.2785 0.6469 0.8458 0.045 Uiso 1 1 d G U . . .
O7 O 0.8467(6) 0.7560(4) 1.0226(2) 0.0249(7) Uani 1 1 d . . . . .
H6 H 0.8503 0.8120 0.9657 0.037 Uiso 1 1 d R U . . .
H7 H 0.9468 0.8422 1.0702 0.037 Uiso 1 1 d R U . . .
N1 N 0.2735(6) 0.1507(5) 0.5174(2) 0.0165(7) Uani 1 1 d . . . . .
N2 N 0.1735(6) 0.0928(5) 0.4150(3) 0.0167(7) Uani 1 1 d . . . . .
C1 C 0.2557(8) 0.1045(6) 0.2344(3) 0.0192(9) Uani 1 1 d . . . . .
C2 C 0.3548(8) 0.1664(6) 0.3510(3) 0.0152(8) Uani 1 1 d . . . . .
C3 C 0.5842(8) 0.2768(6) 0.4153(3) 0.0166(8) Uani 1 1 d . . . . .
H3 H 0.7416 0.3449 0.3931 0.020 Uiso 1 1 calc R U . . .
C4 C 0.5218(7) 0.2609(6) 0.5198(3) 0.0146(8) Uani 1 1 d . . . . .
C5 C 0.6520(8) 0.3197(6) 0.6331(3) 0.0175(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 1.912(3) . ?
Cu1 N2 1.916(3) 2_556 ?
Cu1 O1 1.994(3) . ?
Cu1 O3 2.000(3) 2_556 ?
Cu2 O5 2.001(2) 2_767 ?
Cu2 O5 2.001(2) . ?
Cu2 O6 2.057(2) 2_767 ?
Cu2 O6 2.057(2) . ?
Cu2 O7 2.082(3) . ?
Cu2 O7 2.082(3) 2_767 ?
O1 C5 1.290(5) . ?
O2 C5 1.232(5) . ?
O3 C1 1.293(5) . ?
O3 Cu1 2.000(3) 2_556 ?
O4 C1 1.227(5) . ?
O5 H1 0.8513 . ?
O5 H2 0.8541 . ?
O6 H4 0.8515 . ?
O6 H5 0.8508 . ?
O7 H6 0.8502 . ?
O7 H7 0.8479 . ?
N1 N2 1.330(4) . ?
N1 C4 1.342(5) . ?
N2 C2 1.340(5) . ?
N2 Cu1 1.916(3) 2_556 ?
C1 C2 1.496(5) . ?
C2 C3 1.401(5) . ?
C3 C4 1.389(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.498(5) . ?

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 N2 94.39(13) . 2_556 ?
N1 Cu1 O1 80.11(12) . . ?
N2 Cu1 O1 171.41(13) 2_556 . ?
N1 Cu1 O3 174.37(12) . 2_556 ?
N2 Cu1 O3 80.13(12) 2_556 2_556 ?
O1 Cu1 O3 105.19(11) . 2_556 ?
O5 Cu2 O5 180.0 2_767 . ?
O5 Cu2 O6 88.04(18) 2_767 2_767 ?
O5 Cu2 O6 91.96(18) . 2_767 ?
O5 Cu2 O6 91.96(8) 2_767 . ?
O5 Cu2 O6 88.04(8) . . ?
O6 Cu2 O6 180(3) 2_767 . ?
O5 Cu2 O7 90.10(13) 2_767 . ?
O5 Cu2 O7 89.90(13) . . ?
O6 Cu2 O7 89(3) 2_767 . ?
O6 Cu2 O7 91.17(12) . . ?
O5 Cu2 O7 89.90(13) 2_767 2_767 ?
O5 Cu2 O7 90.10(13) . 2_767 ?
O6 Cu2 O7 91(3) 2_767 2_767 ?
O6 Cu2 O7 88.83(12) . 2_767 ?
O7 Cu2 O7 180.0 . 2_767 ?
C5 O1 Cu1 115.7(2) . . ?
C1 O3 Cu1 115.8(2) . 2_556 ?
Cu2 O5 H1 127.3 . . ?
Cu2 O5 H2 124.5 . . ?
H1 O5 H2 104.0 . . ?
Cu2 O6 H4 126.4 . . ?
Cu2 O6 H5 128.6 . . ?
H4 O6 H5 104.3 . . ?
Cu2 O7 H6 110.1 . . ?
Cu2 O7 H7 110.0 . . ?
H6 O7 H7 104.7 . . ?
N2 N1 C4 108.6(3) . . ?
N2 N1 Cu1 133.0(3) . . ?
C4 N1 Cu1 118.4(3) . . ?
N1 N2 C2 109.1(3) . . ?
N1 N2 Cu1 132.4(3) . 2_556 ?
C2 N2 Cu1 117.8(3) . 2_556 ?
O4 C1 O3 124.1(4) . . ?
O4 C1 C2 122.0(4) . . ?
O3 C1 C2 114.0(3) . . ?
N2 C2 C3 108.9(3) . . ?
N2 C2 C1 111.8(3) . . ?
C3 C2 C1 139.2(4) . . ?
C4 C3 C2 103.8(3) . . ?
C4 C3 H3 128.1 . . ?
C2 C3 H3 128.1 . . ?
N1 C4 C3 109.6(3) . . ?
N1 C4 C5 111.1(3) . . ?
C3 C4 C5 139.2(4) . . ?
O2 C5 O1 123.8(4) . . ?
O2 C5 C4 121.9(4) . . ?
O1 C5 C4 114.2(3) . . ?

_refine_diff_density_max         0.585
_refine_diff_density_min         -0.681
_refine_diff_density_rms         0.128

####################################################################### 
# 
# 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_compound4
_database_code_depnum_ccdc_archive 'CCDC 2219406'
loop_
_audit_author_name
_audit_author_address
'Jaursup Boonmak'
;Khon Kaen University
Thailand
;
_audit_update_record             
;
2023-04-18 deposited with the CCDC.	2023-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 Cu2 N8 O10'
_chemical_formula_weight         659.52

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                   6.338(3)
_cell_length_b                   7.373(3)
_cell_length_c                   13.513(6)
_cell_angle_alpha                76.802(13)
_cell_angle_beta                 82.568(14)
_cell_angle_gamma                72.681(14)
_cell_volume                     585.6(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4691
_cell_measurement_theta_min      2.9545
_cell_measurement_theta_max      24.5295

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.870
_exptl_crystal_F_000             334
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    1.893
_shelx_estimated_absorpt_T_min   0.848
_shelx_estimated_absorpt_T_max   0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6994
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS-2014/5
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  
;
Bruker D8 QUEST PHOTON 100
;
_diffrn_measurement_method       '\fandω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15904
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.954
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_full        24.992
_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             2057
_reflns_number_gt                1677
_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       BrukerAPEX2
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    SHELXL
_computing_publication_material  SHELXL
_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)+(0.0206P)²+0.6592P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2057
_refine_ls_number_parameters     189
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_ref         0.0636
_refine_ls_wR_factor_gt          0.0585
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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 1.15790(6) 0.40122(5) 0.62659(3) 0.02147(13) Uani 1 1 d . . . . .
O1 O 1.1610(3) 0.1512(3) 0.72801(15) 0.0239(5) Uani 1 1 d . . . . .
O2 O 1.0029(4) -0.0909(3) 0.76879(15) 0.0286(5) Uani 1 1 d . . . . .
O3 O 0.6057(3) 0.5012(3) 0.33343(14) 0.0235(5) Uani 1 1 d . . . . .
O4 O 0.4488(4) 0.2580(3) 0.37641(17) 0.0351(6) Uani 1 1 d . . . . .
O5 O 0.9105(4) 0.5761(3) 0.73528(17) 0.0283(5) Uani 1 1 d D . . . .
N1 N 0.9563(4) 0.3123(3) 0.56815(17) 0.0222(6) Uani 1 1 d . . . . .
N2 N 0.8402(4) 0.3867(3) 0.48608(17) 0.0224(6) Uani 1 1 d . . . . .
N3 N 0.5062(5) 0.6313(4) 0.1363(2) 0.0374(7) Uani 1 1 d . . . . .
H3 H 0.4999 0.5750 0.1993 0.045 Uiso 1 1 calc R U . . .
N4 N 0.5346(4) 0.9090(4) -0.16090(19) 0.0311(7) Uani 1 1 d . . . . .
H4A H 0.4147 0.9643 -0.1920 0.037 Uiso 1 1 calc R U . . .
H4B H 0.6604 0.9149 -0.1920 0.037 Uiso 1 1 calc R U . . .
C1 C 1.0286(5) 0.0588(4) 0.7117(2) 0.0196(7) Uani 1 1 d . . . . .
C2 C 0.9047(5) 0.1504(4) 0.6182(2) 0.0193(7) Uani 1 1 d . . . . .
C3 C 0.7480(5) 0.1173(4) 0.5656(2) 0.0203(7) Uani 1 1 d . . . . .
H3A H 0.6826 0.0159 0.5824 0.024 Uiso 1 1 calc R U . . .
C4 C 0.7127(5) 0.2711(4) 0.4823(2) 0.0189(7) Uani 1 1 d . . . . .
C5 C 0.5770(5) 0.3429(4) 0.3921(2) 0.0203(7) Uani 1 1 d . . . . .
C6 C 0.7020(6) 0.6380(5) 0.0878(3) 0.0380(9) Uani 1 1 d . . . . .
H6 H 0.8298 0.5819 0.1231 0.046 Uiso 1 1 calc R U . . .
C7 C 0.7189(6) 0.7242(5) -0.0111(2) 0.0317(8) Uani 1 1 d . . . . .
H7 H 0.8575 0.7241 -0.0437 0.038 Uiso 1 1 calc R U . . .
C8 C 0.5255(5) 0.8151(4) -0.0654(2) 0.0250(7) Uani 1 1 d . . . . .
C9 C 0.3223(5) 0.8022(5) -0.0118(2) 0.0317(8) Uani 1 1 d . . . . .
H9 H 0.1909 0.8559 -0.0446 0.038 Uiso 1 1 calc R U . . .
C10 C 0.3188(6) 0.7117(5) 0.0873(3) 0.0372(9) Uani 1 1 d . . . . .
H10 H 0.1840 0.7049 0.1221 0.045 Uiso 1 1 calc R U . . .
H2 H 0.947(5) 0.676(3) 0.737(2) 0.034(10) Uiso 1 1 d D . . . .
H1 H 0.792(4) 0.626(4) 0.705(3) 0.055(13) Uiso 1 1 d 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 N1 1.919(2) . ?
Cu1 N2 1.919(2) 2_766 ?
Cu1 O3 2.021(2) 2_766 ?
Cu1 O1 2.027(2) . ?
Cu1 O5 2.312(2) . ?
O1 C1 1.294(3) . ?
O2 C1 1.235(3) . ?
O3 C5 1.300(3) . ?
O3 Cu1 2.021(2) 2_766 ?
O4 C5 1.227(3) . ?
O5 H2 0.842(10) . ?
O5 H1 0.846(10) . ?
N1 N2 1.329(3) . ?
N1 C2 1.340(4) . ?
N2 C4 1.350(3) . ?
N2 Cu1 1.919(2) 2_766 ?
N3 C6 1.336(4) . ?
N3 C10 1.343(4) . ?
N3 H3 0.8600 . ?
N4 C8 1.320(4) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
C1 C2 1.490(4) . ?
C2 C3 1.399(4) . ?
C3 C4 1.390(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.487(4) . ?
C6 C7 1.347(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.418(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.412(4) . ?
C9 C10 1.354(4) . ?
C9 H9 0.9300 . ?
C10 H10 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
N1 Cu1 N2 93.73(10) . 2_766 ?
N1 Cu1 O3 171.20(9) . 2_766 ?
N2 Cu1 O3 80.05(9) 2_766 2_766 ?
N1 Cu1 O1 79.68(9) . . ?
N2 Cu1 O1 170.65(9) 2_766 . ?
O3 Cu1 O1 105.72(8) 2_766 . ?
N1 Cu1 O5 99.35(10) . . ?
N2 Cu1 O5 97.47(10) 2_766 . ?
O3 Cu1 O5 87.71(9) 2_766 . ?
O1 Cu1 O5 90.19(9) . . ?
C1 O1 Cu1 115.38(17) . . ?
C5 O3 Cu1 115.14(17) . 2_766 ?
Cu1 O5 H2 110(2) . . ?
Cu1 O5 H1 106(3) . . ?
H2 O5 H1 100.9(15) . . ?
N2 N1 C2 109.2(2) . . ?
N2 N1 Cu1 132.34(19) . . ?
C2 N1 Cu1 118.32(19) . . ?
N1 N2 C4 108.5(2) . . ?
N1 N2 Cu1 133.43(19) . 2_766 ?
C4 N2 Cu1 117.78(19) . 2_766 ?
C6 N3 C10 120.5(3) . . ?
C6 N3 H3 119.8 . . ?
C10 N3 H3 119.8 . . ?
C8 N4 H4A 120.0 . . ?
C8 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
O2 C1 O1 123.6(3) . . ?
O2 C1 C2 122.2(3) . . ?
O1 C1 C2 114.2(2) . . ?
N1 C2 C3 109.0(2) . . ?
N1 C2 C1 112.3(2) . . ?
C3 C2 C1 138.7(3) . . ?
C4 C3 C2 104.0(2) . . ?
C4 C3 H3A 128.0 . . ?
C2 C3 H3A 128.0 . . ?
N2 C4 C3 109.3(2) . . ?
N2 C4 C5 112.3(2) . . ?
C3 C4 C5 138.5(3) . . ?
O4 C5 O3 124.0(3) . . ?
O4 C5 C4 121.7(3) . . ?
O3 C5 C4 114.3(2) . . ?
N3 C6 C7 121.6(3) . . ?
N3 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C6 C7 C8 120.0(3) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
N4 C8 C9 121.7(3) . . ?
N4 C8 C7 121.8(3) . . ?
C9 C8 C7 116.6(3) . . ?
C10 C9 C8 119.9(3) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
N3 C10 C9 121.3(3) . . ?
N3 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?

_refine_diff_density_max         0.359
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.072

####################################################################### 
# 
# 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_compound5
_database_code_depnum_ccdc_archive 'CCDC 2219407'
loop_
_audit_author_name
_audit_author_address
'Jaursup Boonmak'
;Khon Kaen University
Thailand
;
_audit_update_record             
;
2022-11-14 deposited with the CCDC.	2023-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H44 Cu4 N12 O20'
_chemical_formula_weight         1339.09

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                   11.8290(3)
_cell_length_b                   8.5810(3)
_cell_length_c                   24.3140(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.2730(10)
_cell_angle_gamma                90
_cell_volume                     2467.96(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9528
_cell_measurement_theta_min      3.040
_cell_measurement_theta_max      26.2735

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.802
_exptl_crystal_F_000             1360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.796
_shelx_estimated_absorpt_T_min   0.589
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6714
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS-2014/5
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  
;
Bruker D8 QUEST PHOTON 100
;
_diffrn_measurement_method       '\fandω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            55439
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.906
_diffrn_reflns_theta_max         26.414
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5074
_reflns_number_gt                4136
_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      BrukerAPEX2
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    SHELXL
_computing_publication_material  SHELXL
_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)+(0.0334P)²+1.7643P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5074
_refine_ls_number_parameters     386
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0293
_refine_ls_wR_factor_ref         0.0722
_refine_ls_wR_factor_gt          0.0667
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.053
_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 0.71763(2) 0.45127(3) 0.53145(2) 0.02795(9) Uani 1 1 d . . . . .
Cu2 Cu 0.98863(2) 0.19557(3) 0.49350(2) 0.02712(9) Uani 1 1 d . . . . .
O1 O 0.65948(13) 0.49036(19) 0.60794(6) 0.0307(4) Uani 1 1 d . . . . .
O2 O 0.68922(13) 0.4226(2) 0.69547(6) 0.0346(4) Uani 1 1 d . . . . .
O3 O 1.07622(13) 0.05086(19) 0.54346(6) 0.0287(4) Uani 1 1 d . . . . .
O4 O 1.09374(15) -0.0099(2) 0.63293(7) 0.0410(5) Uani 1 1 d . . . . .
O5 O 0.65440(13) 0.63034(19) 0.48851(7) 0.0326(4) Uani 1 1 d . . . . .
O6 O 0.67111(15) 0.7540(2) 0.40809(7) 0.0414(4) Uani 1 1 d . . . . .
O7 O 1.09172(13) 0.2310(2) 0.42977(7) 0.0339(4) Uani 1 1 d . . . . .
O8 O 1.10122(15) 0.3526(2) 0.34906(8) 0.0461(5) Uani 1 1 d . . . . .
O9 O 0.57519(15) 0.2948(2) 0.50588(9) 0.0440(5) Uani 1 1 d D . . . .
O10 O 0.68149(19) 0.0340(3) 0.46671(11) 0.0588(6) Uani 1 1 d D . . . .
N1 N 0.81161(15) 0.3054(2) 0.57174(7) 0.0285(4) Uani 1 1 d . . . . .
N2 N 0.89762(15) 0.2120(2) 0.55835(7) 0.0286(4) Uani 1 1 d . . . . .
N3 N 0.81355(16) 0.4396(2) 0.46799(8) 0.0298(4) Uani 1 1 d . . . . .
N4 N 0.90451(15) 0.3551(2) 0.45553(8) 0.0306(4) Uani 1 1 d . . . . .
N5 N -0.21455(18) 0.3605(3) 0.86079(12) 0.0578(8) Uani 1 1 d . . . . .
H5 H -0.2637 0.2967 0.8738 0.069 Uiso 1 1 calc R U . . .
N6 N 0.47914(15) 0.6199(2) 0.66020(8) 0.0302(4) Uani 1 1 d . . . . .
H6 H 0.5373 0.5866 0.6426 0.036 Uiso 1 1 calc R U . . .
C1 C 0.71063(17) 0.4114(3) 0.64649(9) 0.0264(5) Uani 1 1 d . . . . .
C2 C 0.80006(18) 0.3041(3) 0.62626(9) 0.0261(5) Uani 1 1 d . . . . .
C3 C 0.88059(18) 0.2066(3) 0.64937(9) 0.0277(5) Uani 1 1 d . . . . .
H3 H 0.8916 0.1832 0.6864 0.033 Uiso 1 1 calc R U . . .
C4 C 0.94111(18) 0.1518(3) 0.60456(9) 0.0251(5) Uani 1 1 d . . . . .
C5 C 1.04497(19) 0.0555(3) 0.59546(9) 0.0281(5) Uani 1 1 d . . . . .
C6 C 0.70169(18) 0.6550(3) 0.44129(10) 0.0281(5) Uani 1 1 d . . . . .
C7 C 0.79973(18) 0.5502(3) 0.42981(9) 0.0256(5) Uani 1 1 d . . . . .
C8 C 0.88430(19) 0.5357(3) 0.39057(10) 0.0286(5) Uani 1 1 d . . . . .
H8 H 0.8950 0.5958 0.3592 0.034 Uiso 1 1 calc R U . . .
C9 C 0.94875(18) 0.4113(3) 0.40880(9) 0.0272(5) Uani 1 1 d . . . . .
C10 C 1.05449(19) 0.3284(3) 0.39296(11) 0.0315(5) Uani 1 1 d . . . . .
C11 C -0.2043(2) 0.3728(3) 0.80682(14) 0.0528(8) Uani 1 1 d . . . . .
H11 H -0.2493 0.3123 0.7837 0.063 Uiso 1 1 calc R U . . .
C12 C -0.1279(2) 0.4742(3) 0.78502(11) 0.0395(6) Uani 1 1 d . . . . .
H12 H -0.1202 0.4826 0.7471 0.047 Uiso 1 1 calc R U . . .
C13 C -0.06189(18) 0.5646(3) 0.81968(10) 0.0286(5) Uani 1 1 d . . . . .
C14 C -0.0741(2) 0.5449(3) 0.87578(10) 0.0405(6) Uani 1 1 d . . . . .
H14 H -0.0290 0.6013 0.9001 0.049 Uiso 1 1 calc R U . . .
C15 C -0.1523(2) 0.4424(4) 0.89551(13) 0.0544(8) Uani 1 1 d . . . . .
H15 H -0.1617 0.4303 0.9332 0.065 Uiso 1 1 calc R U . . .
C16 C 0.01518(19) 0.6873(3) 0.79654(11) 0.0332(6) Uani 1 1 d . . . . .
H16A H 0.0369 0.7573 0.8261 0.040 Uiso 1 1 calc R U . . .
H16B H -0.0270 0.7478 0.7697 0.040 Uiso 1 1 calc R U . . .
C17 C 0.12201(19) 0.6272(3) 0.76930(10) 0.0322(5) Uani 1 1 d . . . . .
H17A H 0.1025 0.5556 0.7399 0.039 Uiso 1 1 calc R U . . .
H17B H 0.1682 0.5719 0.7960 0.039 Uiso 1 1 calc R U . . .
C18 C 0.18776(19) 0.7658(3) 0.74615(11) 0.0325(6) Uani 1 1 d . . . . .
H18A H 0.1389 0.8237 0.7214 0.039 Uiso 1 1 calc R U . . .
H18B H 0.2087 0.8345 0.7762 0.039 Uiso 1 1 calc R U . . .
C19 C 0.3957(2) 0.6866(3) 0.63219(10) 0.0337(6) Uani 1 1 d . . . . .
H19 H 0.4011 0.6981 0.5943 0.040 Uiso 1 1 calc R U . . .
C20 C 0.30142(19) 0.7387(3) 0.65929(10) 0.0312(5) Uani 1 1 d . . . . .
H20 H 0.2434 0.7872 0.6398 0.037 Uiso 1 1 calc R U . . .
C21 C 0.29279(18) 0.7190(2) 0.71579(9) 0.0247(5) Uani 1 1 d . . . . .
C22 C 0.38322(19) 0.6523(3) 0.74349(9) 0.0286(5) Uani 1 1 d . . . . .
H22 H 0.3810 0.6412 0.7815 0.034 Uiso 1 1 calc R U . . .
C23 C 0.47581(19) 0.6027(3) 0.71481(10) 0.0300(5) Uani 1 1 d . . . . .
H23 H 0.5364 0.5572 0.7333 0.036 Uiso 1 1 calc R U . . .
H1 H 0.5055(9) 0.296(3) 0.5088(12) 0.048(9) Uiso 1 1 d D . . . .
H2 H 0.5898(19) 0.2043(17) 0.4958(12) 0.051(9) Uiso 1 1 d D . . . .
H7 H 0.661(2) -0.042(3) 0.4471(12) 0.073(12) Uiso 1 1 d D . . . .
H4 H 0.7514(9) 0.022(4) 0.4686(15) 0.084(13) Uiso 1 1 d 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 N3 1.9222(18) . ?
Cu1 N1 1.9369(18) . ?
Cu1 O5 2.0007(16) . ?
Cu1 O1 2.0141(15) . ?
Cu1 O9 2.2402(18) . ?
Cu2 N2 1.9186(18) . ?
Cu2 N4 1.9257(19) . ?
Cu2 O7 1.9997(16) . ?
Cu2 O3 2.0196(15) . ?
Cu2 O3 2.4210(16) 3_756 ?
O1 C1 1.303(3) . ?
O2 C1 1.222(3) . ?
O3 C5 1.320(3) . ?
O3 Cu2 2.4211(16) 3_756 ?
O4 C5 1.214(3) . ?
O5 C6 1.297(3) . ?
O6 C6 1.225(3) . ?
O7 C10 1.300(3) . ?
O8 C10 1.222(3) . ?
O9 H1 0.828(10) . ?
O9 H2 0.833(10) . ?
O10 H7 0.840(10) . ?
O10 H4 0.834(10) . ?
N1 C2 1.333(3) . ?
N1 N2 1.337(2) . ?
N2 C4 1.337(3) . ?
N3 N4 1.334(2) . ?
N3 C7 1.337(3) . ?
N4 C9 1.343(3) . ?
N5 C15 1.320(4) . ?
N5 C11 1.322(4) . ?
N5 H5 0.8600 . ?
N6 C19 1.326(3) . ?
N6 C23 1.337(3) . ?
N6 H6 0.8600 . ?
C1 C2 1.488(3) . ?
C2 C3 1.385(3) . ?
C3 C4 1.388(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.498(3) . ?
C6 C7 1.495(3) . ?
C7 C8 1.391(3) . ?
C8 C9 1.383(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.491(3) . ?
C11 C12 1.364(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.384(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.383(3) . ?
C13 C16 1.504(3) . ?
C14 C15 1.365(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.520(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.530(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C21 1.503(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.373(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.388(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.385(3) . ?
C22 C23 1.369(3) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Cu1 N1 91.88(8) . . ?
N3 Cu1 O5 80.89(7) . . ?
N1 Cu1 O5 166.51(8) . . ?
N3 Cu1 O1 162.82(8) . . ?
N1 Cu1 O1 80.69(7) . . ?
O5 Cu1 O1 103.03(6) . . ?
N3 Cu1 O9 101.08(8) . . ?
N1 Cu1 O9 100.50(8) . . ?
O5 Cu1 O9 92.10(7) . . ?
O1 Cu1 O9 95.52(7) . . ?
N2 Cu2 N4 92.93(8) . . ?
N2 Cu2 O7 166.48(8) . . ?
N4 Cu2 O7 80.56(7) . . ?
N2 Cu2 O3 80.75(7) . . ?
N4 Cu2 O3 171.09(7) . . ?
O7 Cu2 O3 104.28(6) . . ?
N2 Cu2 O3 101.02(7) . 3_756 ?
N4 Cu2 O3 106.31(7) . 3_756 ?
O7 Cu2 O3 92.20(6) . 3_756 ?
O3 Cu2 O3 81.20(6) . 3_756 ?
C1 O1 Cu1 114.72(13) . . ?
C5 O3 Cu2 114.35(13) . . ?
C5 O3 Cu2 107.02(14) . 3_756 ?
Cu2 O3 Cu2 98.80(6) . 3_756 ?
C6 O5 Cu1 115.17(13) . . ?
C10 O7 Cu2 115.18(13) . . ?
Cu1 O9 H1 135.8(17) . . ?
Cu1 O9 H2 119.0(17) . . ?
H1 O9 H2 104.1(15) . . ?
H7 O10 H4 102.4(15) . . ?
C2 N1 N2 108.58(18) . . ?
C2 N1 Cu1 116.57(14) . . ?
N2 N1 Cu1 134.42(15) . . ?
N1 N2 C4 108.48(18) . . ?
N1 N2 Cu2 132.45(15) . . ?
C4 N2 Cu2 116.55(14) . . ?
N4 N3 C7 108.92(18) . . ?
N4 N3 Cu1 133.68(15) . . ?
C7 N3 Cu1 116.73(15) . . ?
N3 N4 C9 108.35(18) . . ?
N3 N4 Cu2 133.89(15) . . ?
C9 N4 Cu2 117.30(15) . . ?
C15 N5 C11 122.6(2) . . ?
C15 N5 H5 118.7 . . ?
C11 N5 H5 118.7 . . ?
C19 N6 C23 122.2(2) . . ?
C19 N6 H6 118.9 . . ?
C23 N6 H6 118.9 . . ?
O2 C1 O1 124.2(2) . . ?
O2 C1 C2 121.4(2) . . ?
O1 C1 C2 114.35(19) . . ?
N1 C2 C3 109.58(19) . . ?
N1 C2 C1 113.55(19) . . ?
C3 C2 C1 136.8(2) . . ?
C2 C3 C4 104.03(19) . . ?
C2 C3 H3 128.0 . . ?
C4 C3 H3 128.0 . . ?
N2 C4 C3 109.32(19) . . ?
N2 C4 C5 113.66(19) . . ?
C3 C4 C5 136.8(2) . . ?
O4 C5 O3 124.8(2) . . ?
O4 C5 C4 122.1(2) . . ?
O3 C5 C4 113.08(18) . . ?
O6 C6 O5 124.7(2) . . ?
O6 C6 C7 121.4(2) . . ?
O5 C6 C7 113.93(19) . . ?
N3 C7 C8 109.06(19) . . ?
N3 C7 C6 112.94(19) . . ?
C8 C7 C6 138.0(2) . . ?
C9 C8 C7 104.3(2) . . ?
C9 C8 H8 127.9 . . ?
C7 C8 H8 127.9 . . ?
N4 C9 C8 109.38(19) . . ?
N4 C9 C10 112.2(2) . . ?
C8 C9 C10 138.4(2) . . ?
O8 C10 O7 123.9(2) . . ?
O8 C10 C9 121.8(2) . . ?
O7 C10 C9 114.3(2) . . ?
N5 C11 C12 120.0(3) . . ?
N5 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C13 119.6(3) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C14 C13 C12 118.1(2) . . ?
C14 C13 C16 121.4(2) . . ?
C12 C13 C16 120.4(2) . . ?
C15 C14 C13 120.0(3) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
N5 C15 C14 119.7(3) . . ?
N5 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C13 C16 C17 115.6(2) . . ?
C13 C16 H16A 108.4 . . ?
C17 C16 H16A 108.4 . . ?
C13 C16 H16B 108.4 . . ?
C17 C16 H16B 108.4 . . ?
H16A C16 H16B 107.4 . . ?
C16 C17 C18 108.78(19) . . ?
C16 C17 H17A 109.9 . . ?
C18 C17 H17A 109.9 . . ?
C16 C17 H17B 109.9 . . ?
C18 C17 H17B 109.9 . . ?
H17A C17 H17B 108.3 . . ?
C21 C18 C17 113.33(19) . . ?
C21 C18 H18A 108.9 . . ?
C17 C18 H18A 108.9 . . ?
C21 C18 H18B 108.9 . . ?
C17 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
N6 C19 C20 119.9(2) . . ?
N6 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C19 C20 C21 119.9(2) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C22 C21 C20 118.1(2) . . ?
C22 C21 C18 120.7(2) . . ?
C20 C21 C18 121.2(2) . . ?
C23 C22 C21 119.9(2) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
N6 C23 C22 119.9(2) . . ?
N6 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?

_refine_diff_density_max         0.363
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.068

