# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2022

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 2116312'
_audit_update_record             
;
2021-10-18 deposited with the CCDC.	2022-09-16 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         'C12 H9 Cu N5 O4'
_chemical_formula_sum            'C12 H9 Cu N5 O4'
_chemical_formula_weight         350.78

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

_space_group_crystal_system      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                   6.8825(3)
_cell_length_b                   12.7580(7)
_cell_length_c                   14.6681(6)
_cell_angle_alpha                88.831(2)
_cell_angle_beta                 83.151(2)
_cell_angle_gamma                82.229(2)
_cell_volume                     1267.01(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2715
_cell_measurement_theta_min      3.22
_cell_measurement_theta_max      25.34

_exptl_crystal_description       sheet
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.839
_exptl_crystal_F_000             708
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.753
_shelx_estimated_absorpt_T_min   0.779
_shelx_estimated_absorpt_T_max   0.933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6481
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 2 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10262
_diffrn_reflns_av_unetI/netI     0.0647
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.165
_diffrn_reflns_theta_max         25.374
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4639
_reflns_number_gt                3392
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0355P)²+1.0440P] 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         4639
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.0990
_refine_ls_wR_factor_gt          0.0828
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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
C1 C 0.2841(6) 0.0896(3) 0.5838(3) 0.0201(9) Uani 1 1 d . . . . .
C2 C 0.2880(6) -0.1555(3) 0.6780(3) 0.0204(9) Uani 1 1 d . . . . .
H2 H 0.2671 -0.2047 0.6336 0.024 Uiso 1 1 calc R U . . .
C3 C 0.3310(6) 0.3244(3) 0.4292(3) 0.0214(9) Uani 1 1 d . . . . .
H3 H 0.3822 0.3898 0.4307 0.026 Uiso 1 1 calc R U . . .
C4 C 0.3442(6) 0.2573(3) 0.5033(3) 0.0206(9) Uani 1 1 d . . . . .
H4 H 0.3975 0.2776 0.5561 0.025 Uiso 1 1 calc R U . . .
C5 C 0.2782(6) 0.1590(3) 0.5001(3) 0.0183(8) Uani 1 1 d . . . . .
C6 C 0.2040(6) 0.1318(3) 0.4211(3) 0.0203(9) Uani 1 1 d . . . . .
H6 H 0.1630 0.0643 0.4159 0.024 Uiso 1 1 calc R U . . .
C7 C 0.1910(6) 0.2047(3) 0.3502(3) 0.0185(8) Uani 1 1 d . . . . .
H7 H 0.1394 0.1858 0.2965 0.022 Uiso 1 1 calc R U . . .
C8 C 0.3142(6) -0.1859(3) 0.7728(3) 0.0188(9) Uani 1 1 d . . . . .
C9 C 0.3139(6) -0.2887(3) 0.8058(3) 0.0237(9) Uani 1 1 d . . . . .
H9 H 0.2939 -0.3436 0.7665 0.028 Uiso 1 1 calc R U . . .
C10 C 0.3428(6) -0.3105(3) 0.8966(3) 0.0244(10) Uani 1 1 d . . . . .
H10 H 0.3388 -0.3798 0.9211 0.029 Uiso 1 1 calc R U . . .
C11 C 0.3775(6) -0.2295(3) 0.9502(3) 0.0240(9) Uani 1 1 d . . . . .
H11 H 0.4009 -0.2427 1.0122 0.029 Uiso 1 1 calc R U . . .
C12 C 0.3781(6) -0.1286(3) 0.9136(3) 0.0214(9) Uani 1 1 d . . . . .
H12 H 0.4041 -0.0736 0.9513 0.026 Uiso 1 1 calc R U . . .
C13 C 0.1698(6) 0.3546(3) 0.0860(3) 0.0193(9) Uani 1 1 d . . . . .
C14 C 0.2266(7) 0.5947(3) 0.1628(3) 0.0294(10) Uani 1 1 d . . . . .
H14 H 0.2513 0.6399 0.1117 0.035 Uiso 1 1 calc R U . . .
C15 C 0.1532(6) 0.1160(3) -0.0565(3) 0.0220(9) Uani 1 1 d . . . . .
H15 H 0.1158 0.0472 -0.0471 0.026 Uiso 1 1 calc R U . . .
C16 C 0.1284(6) 0.1831(3) 0.0170(3) 0.0207(9) Uani 1 1 d . . . . .
H16 H 0.0798 0.1598 0.0762 0.025 Uiso 1 1 calc R U . . .
C17 C 0.1747(6) 0.2856(3) 0.0044(3) 0.0179(8) Uani 1 1 d . . . . .
C18 C 0.2351(6) 0.3170(3) -0.0847(3) 0.0223(9) Uani 1 1 d . . . . .
H18 H 0.2572 0.3881 -0.0972 0.027 Uiso 1 1 calc R U . . .
C19 C 0.2627(6) 0.2440(3) -0.1548(3) 0.0225(9) Uani 1 1 d . . . . .
H19 H 0.3080 0.2660 -0.2149 0.027 Uiso 1 1 calc R U . . .
C20 C 0.2166(6) 0.6312(3) 0.2575(3) 0.0248(9) Uani 1 1 d . . . . .
C21 C 0.2295(7) 0.7345(4) 0.2799(3) 0.0324(11) Uani 1 1 d . . . . .
H21 H 0.2519 0.7855 0.2331 0.039 Uiso 1 1 calc R U . . .
C22 C 0.2093(7) 0.7627(3) 0.3717(3) 0.0300(10) Uani 1 1 d . . . . .
H22 H 0.2181 0.8331 0.3888 0.036 Uiso 1 1 calc R U . . .
C23 C 0.1763(6) 0.6870(3) 0.4372(3) 0.0263(10) Uani 1 1 d . . . . .
H23 H 0.1597 0.7045 0.5005 0.032 Uiso 1 1 calc R U . . .
C24 C 0.1673(6) 0.5852(3) 0.4100(3) 0.0246(9) Uani 1 1 d . . . . .
H24 H 0.1448 0.5334 0.4562 0.029 Uiso 1 1 calc R U . . .
Cu1 Cu 0.31467(8) 0.03571(4) 0.75993(3) 0.02031(14) Uani 1 1 d . . . . .
Cu2 Cu 0.16397(7) 0.41344(4) 0.26269(3) 0.01907(14) Uani 1 1 d . . . . .
N1 N 0.2767(5) -0.0126(3) 0.5738(2) 0.0201(7) Uani 1 1 d . . . . .
N2 N 0.2952(5) -0.0576(3) 0.6594(2) 0.0167(7) Uani 1 1 d . . . . .
N3 N 0.2485(5) 0.3016(3) 0.3541(2) 0.0191(7) Uani 1 1 d . . . . .
N4 N 0.3433(4) -0.1059(3) 0.8273(2) 0.0170(7) Uani 1 1 d . . . . .
N5 N 0.2013(5) 0.4535(3) 0.0695(2) 0.0236(8) Uani 1 1 d . . . . .
N6 N 0.2006(5) 0.4995(3) 0.1531(2) 0.0205(7) Uani 1 1 d . . . . .
N7 N 0.2284(5) 0.1432(3) -0.1416(2) 0.0194(7) Uani 1 1 d . . . . .
N8 N 0.1886(5) 0.5553(3) 0.3221(2) 0.0214(8) Uani 1 1 d . . . . .
N9 N 0.7526(5) 0.0206(3) 0.8105(2) 0.0223(8) Uani 1 1 d . . . . .
N10 N -0.2561(5) 0.4967(3) 0.3371(2) 0.0248(8) Uani 1 1 d . . . . .
O1 O 0.2979(4) 0.1374(2) 0.65850(18) 0.0249(7) Uani 1 1 d . . . . .
O2 O 0.1439(4) 0.3119(2) 0.16565(17) 0.0219(6) Uani 1 1 d . . . . .
O3 O 0.6508(4) 0.0299(2) 0.74371(19) 0.0270(7) Uani 1 1 d . . . . .
O4 O 0.6789(5) 0.0566(3) 0.8870(2) 0.0394(8) Uani 1 1 d . . . . .
O5 O 0.9268(4) -0.0226(3) 0.7984(2) 0.0353(8) Uani 1 1 d . . . . .
O6 O -0.1271(4) 0.4163(2) 0.34909(19) 0.0250(7) Uani 1 1 d . . . . .
O7 O -0.2525(6) 0.5391(3) 0.2604(2) 0.0477(10) Uani 1 1 d . . . . .
O8 O -0.3818(5) 0.5266(3) 0.4016(2) 0.0413(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
C1 O1 1.284(5) . ?
C1 N1 1.323(5) . ?
C1 C5 1.500(5) . ?
C2 N2 1.280(5) . ?
C2 C8 1.462(5) . ?
C2 H2 0.9500 . ?
C3 N3 1.352(5) . ?
C3 C4 1.374(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(5) . ?
C6 C7 1.384(5) . ?
C6 H6 0.9500 . ?
C7 N3 1.352(5) . ?
C7 H7 0.9500 . ?
C8 N4 1.358(5) . ?
C8 C9 1.389(5) . ?
C9 C10 1.387(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.374(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(5) . ?
C11 H11 0.9500 . ?
C12 N4 1.336(5) . ?
C12 H12 0.9500 . ?
C13 O2 1.283(4) . ?
C13 N5 1.321(5) . ?
C13 C17 1.494(6) . ?
C14 N6 1.265(5) . ?
C14 C20 1.464(6) . ?
C14 H14 0.9500 . ?
C15 N7 1.351(5) . ?
C15 C16 1.371(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.391(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.392(5) . ?
C18 C19 1.379(6) . ?
C18 H18 0.9500 . ?
C19 N7 1.345(5) . ?
C19 H19 0.9500 . ?
C20 N8 1.358(5) . ?
C20 C21 1.382(6) . ?
C21 C22 1.386(6) . ?
C21 H21 0.9500 . ?
C22 C23 1.370(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.378(6) . ?
C23 H23 0.9500 . ?
C24 N8 1.338(5) . ?
C24 H24 0.9500 . ?
Cu1 N2 1.942(3) . ?
Cu1 O1 1.957(3) . ?
Cu1 N7 1.994(3) 1_556 ?
Cu1 N4 2.039(3) . ?
Cu1 O3 2.288(3) . ?
Cu2 N6 1.939(3) . ?
Cu2 O2 1.974(3) . ?
Cu2 N3 2.014(3) . ?
Cu2 N8 2.060(4) . ?
Cu2 O6 2.236(3) . ?
N1 N2 1.383(4) . ?
N5 N6 1.370(4) . ?
N7 Cu1 1.995(3) 1_554 ?
N9 O4 1.244(4) . ?
N9 O5 1.244(4) . ?
N9 O3 1.266(4) . ?
N10 O8 1.232(5) . ?
N10 O7 1.238(4) . ?
N10 O6 1.286(4) . ?

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 C1 N1 126.9(3) . . ?
O1 C1 C5 115.0(4) . . ?
N1 C1 C5 118.0(4) . . ?
N2 C2 C8 114.8(4) . . ?
N2 C2 H2 122.6 . . ?
C8 C2 H2 122.6 . . ?
N3 C3 C4 122.9(4) . . ?
N3 C3 H3 118.5 . . ?
C4 C3 H3 118.5 . . ?
C3 C4 C5 119.1(4) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 118.5(3) . . ?
C6 C5 C1 123.4(4) . . ?
C4 C5 C1 118.1(4) . . ?
C7 C6 C5 119.0(4) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
N3 C7 C6 122.8(4) . . ?
N3 C7 H7 118.6 . . ?
C6 C7 H7 118.6 . . ?
N4 C8 C9 121.6(4) . . ?
N4 C8 C2 115.0(3) . . ?
C9 C8 C2 123.4(4) . . ?
C10 C9 C8 119.4(4) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C11 C10 C9 118.5(4) . . ?
C11 C10 H10 120.8 . . ?
C9 C10 H10 120.8 . . ?
C10 C11 C12 119.8(4) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
N4 C12 C11 122.3(4) . . ?
N4 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
O2 C13 N5 125.6(4) . . ?
O2 C13 C17 117.4(3) . . ?
N5 C13 C17 116.9(3) . . ?
N6 C14 C20 116.1(4) . . ?
N6 C14 H14 122.0 . . ?
C20 C14 H14 122.0 . . ?
N7 C15 C16 122.9(4) . . ?
N7 C15 H15 118.5 . . ?
C16 C15 H15 118.5 . . ?
C15 C16 C17 119.7(4) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C18 117.5(4) . . ?
C16 C17 C13 119.6(3) . . ?
C18 C17 C13 122.8(4) . . ?
C19 C18 C17 119.4(4) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
N7 C19 C18 122.9(4) . . ?
N7 C19 H19 118.6 . . ?
C18 C19 H19 118.6 . . ?
N8 C20 C21 122.4(4) . . ?
N8 C20 C14 114.3(4) . . ?
C21 C20 C14 123.3(4) . . ?
C20 C21 C22 119.1(4) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
C23 C22 C21 118.7(4) . . ?
C23 C22 H22 120.6 . . ?
C21 C22 H22 120.6 . . ?
C22 C23 C24 119.2(4) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
N8 C24 C23 123.5(4) . . ?
N8 C24 H24 118.3 . . ?
C23 C24 H24 118.3 . . ?
N2 Cu1 O1 79.37(12) . . ?
N2 Cu1 N7 158.68(13) . 1_556 ?
O1 Cu1 N7 95.06(12) . 1_556 ?
N2 Cu1 N4 80.56(13) . . ?
O1 Cu1 N4 159.63(13) . . ?
N7 Cu1 N4 104.95(13) 1_556 . ?
N2 Cu1 O3 98.25(12) . . ?
O1 Cu1 O3 90.17(11) . . ?
N7 Cu1 O3 102.37(12) 1_556 . ?
N4 Cu1 O3 89.25(11) . . ?
N6 Cu2 O2 78.57(12) . . ?
N6 Cu2 N3 154.78(14) . . ?
O2 Cu2 N3 94.75(12) . . ?
N6 Cu2 N8 80.33(13) . . ?
O2 Cu2 N8 158.79(11) . . ?
N3 Cu2 N8 105.30(13) . . ?
N6 Cu2 O6 122.81(12) . . ?
O2 Cu2 O6 102.29(11) . . ?
N3 Cu2 O6 82.30(11) . . ?
N8 Cu2 O6 87.43(12) . . ?
C1 N1 N2 105.8(3) . . ?
C2 N2 N1 124.3(3) . . ?
C2 N2 Cu1 117.8(3) . . ?
N1 N2 Cu1 117.8(2) . . ?
C3 N3 C7 117.4(3) . . ?
C3 N3 Cu2 122.1(3) . . ?
C7 N3 Cu2 119.4(3) . . ?
C12 N4 C8 118.5(3) . . ?
C12 N4 Cu1 130.2(3) . . ?
C8 N4 Cu1 111.3(2) . . ?
C13 N5 N6 106.7(3) . . ?
C14 N6 N5 123.6(3) . . ?
C14 N6 Cu2 118.0(3) . . ?
N5 N6 Cu2 118.3(2) . . ?
C19 N7 C15 117.2(4) . . ?
C19 N7 Cu1 120.8(3) . 1_554 ?
C15 N7 Cu1 121.6(3) . 1_554 ?
C24 N8 C20 117.1(4) . . ?
C24 N8 Cu2 131.5(3) . . ?
C20 N8 Cu2 111.2(3) . . ?
O4 N9 O5 120.8(4) . . ?
O4 N9 O3 119.7(4) . . ?
O5 N9 O3 119.5(4) . . ?
O8 N10 O7 122.5(4) . . ?
O8 N10 O6 118.8(3) . . ?
O7 N10 O6 118.6(4) . . ?
C1 O1 Cu1 110.1(2) . . ?
C13 O2 Cu2 110.7(2) . . ?
N9 O3 Cu1 123.6(2) . . ?
N10 O6 Cu2 115.7(2) . . ?

_refine_diff_density_max         0.606
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.095

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2116313'
_audit_update_record             
;
2021-10-18 deposited with the CCDC.	2022-09-16 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         'C12 H10 Cd N6 O7'
_chemical_formula_sum            'C12 H10 Cd N6 O7'
_chemical_formula_weight         462.66

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'
Cd Cd -0.8075 1.2024 '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                   8.9489(3)
_cell_length_b                   11.3880(4)
_cell_length_c                   15.6833(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.6860(10)
_cell_angle_gamma                90
_cell_volume                     1538.76(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4848
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      25.34

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.997
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.474
_shelx_estimated_absorpt_T_min   0.692
_shelx_estimated_absorpt_T_max   0.809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6833
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 2 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9022
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.965
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             2773
_reflns_number_gt                2425
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0327P)²+1.8637P] 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         2773
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0237
_refine_ls_wR_factor_ref         0.0646
_refine_ls_wR_factor_gt          0.0578
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
C1 C 0.6454(3) 0.7061(3) 0.2713(2) 0.0209(6) Uani 1 1 d . . . . .
C2 C 0.3962(3) 0.7518(3) 0.40536(19) 0.0196(6) Uani 1 1 d . . . . .
H2 H 0.4547 0.7119 0.4568 0.023 Uiso 1 1 calc R U . . .
C3 C 0.9613(3) 0.5360(3) 0.2116(2) 0.0234(6) Uani 1 1 d . . . . .
H3 H 0.9877 0.5160 0.1586 0.028 Uiso 1 1 calc R U . . .
C4 C 0.8334(3) 0.6068(3) 0.2062(2) 0.0229(6) Uani 1 1 d . . . . .
H4 H 0.7739 0.6352 0.1504 0.028 Uiso 1 1 calc R U . . .
C5 C 0.7924(3) 0.6359(2) 0.2828(2) 0.0181(6) Uani 1 1 d . . . . .
C6 C 0.8868(3) 0.5968(3) 0.3631(2) 0.0234(6) Uani 1 1 d . . . . .
H6 H 0.8650 0.6174 0.4172 0.028 Uiso 1 1 calc R U . . .
C7 C 1.0136(3) 0.5273(3) 0.3628(2) 0.0249(7) Uani 1 1 d . . . . .
H7 H 1.0784 0.5014 0.4181 0.030 Uiso 1 1 calc R U . . .
C8 C 0.2444(3) 0.8014(3) 0.40306(19) 0.0190(6) Uani 1 1 d . . . . .
C9 C 0.1872(4) 0.7913(3) 0.4766(2) 0.0240(6) Uani 1 1 d . . . . .
H9 H 0.2447 0.7508 0.5280 0.029 Uiso 1 1 calc R U . . .
C10 C 0.0451(4) 0.8411(3) 0.4737(2) 0.0239(7) Uani 1 1 d . . . . .
H10 H 0.0030 0.8353 0.5230 0.029 Uiso 1 1 calc R U . . .
C11 C -0.0344(3) 0.8995(3) 0.3982(2) 0.0271(7) Uani 1 1 d . . . . .
H11 H -0.1314 0.9357 0.3949 0.033 Uiso 1 1 calc R U . . .
C12 C 0.0294(3) 0.9046(3) 0.3268(2) 0.0242(7) Uani 1 1 d . . . . .
H12 H -0.0267 0.9444 0.2747 0.029 Uiso 1 1 calc R U . . .
Cd1 Cd 0.27547(2) 0.84704(2) 0.20778(2) 0.01893(9) Uani 1 1 d . . . . .
N1 N 0.5919(3) 0.7114(2) 0.34484(17) 0.0220(5) Uani 1 1 d . . . . .
H1A H 0.637(4) 0.669(3) 0.393(2) 0.026 Uiso 1 1 d . U . . .
N2 N 0.4500(3) 0.7623(2) 0.33780(16) 0.0192(5) Uani 1 1 d . . . . .
N3 N 1.0496(3) 0.4946(2) 0.28916(17) 0.0206(5) Uani 1 1 d . . . . .
N4 N 0.1658(3) 0.8563(2) 0.32780(17) 0.0211(5) Uani 1 1 d . . . . .
N5 N -0.0222(3) 0.9373(2) 0.10387(16) 0.0241(6) Uani 1 1 d . . . . .
N6 N 0.2336(3) 0.6765(2) 0.07503(18) 0.0269(6) Uani 1 1 d . . . . .
O1 O 0.5794(3) 0.7519(2) 0.20123(14) 0.0318(5) Uani 1 1 d . . . . .
O2 O 0.0977(2) 0.99697(19) 0.13958(15) 0.0277(5) Uani 1 1 d . . . . .
O3 O -0.0195(3) 0.82967(19) 0.12079(15) 0.0289(5) Uani 1 1 d . . . . .
O4 O -0.1377(3) 0.9848(2) 0.05455(16) 0.0364(6) Uani 1 1 d . . . . .
O5 O 0.2412(3) 0.65356(19) 0.15565(15) 0.0290(5) Uani 1 1 d . . . . .
O6 O 0.2561(2) 0.7825(2) 0.05570(14) 0.0272(5) Uani 1 1 d . . . . .
O7 O 0.2053(3) 0.5993(2) 0.01812(17) 0.0400(6) 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
C1 O1 1.215(4) . ?
C1 N1 1.365(4) . ?
C1 C5 1.507(4) . ?
C2 N2 1.283(4) . ?
C2 C8 1.462(4) . ?
C2 H2 0.9500 . ?
C3 N3 1.344(4) . ?
C3 C4 1.384(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(4) . ?
C6 C7 1.385(4) . ?
C6 H6 0.9500 . ?
C7 N3 1.334(4) . ?
C7 H7 0.9500 . ?
C8 N4 1.352(4) . ?
C8 C9 1.388(4) . ?
C9 C10 1.382(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.376(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(4) . ?
C11 H11 0.9500 . ?
C12 N4 1.335(4) . ?
C12 H12 0.9500 . ?
Cd1 N3 2.288(2) 2_655 ?
Cd1 O5 2.341(2) . ?
Cd1 N4 2.349(3) . ?
Cd1 O2 2.381(2) . ?
Cd1 N2 2.410(2) . ?
Cd1 O6 2.456(2) . ?
Cd1 O3 2.631(2) . ?
N1 N2 1.373(3) . ?
N1 H1A 0.89(4) . ?
N3 Cd1 2.288(2) 2_645 ?
N5 O4 1.236(3) . ?
N5 O3 1.253(3) . ?
N5 O2 1.265(3) . ?
N6 O7 1.230(4) . ?
N6 O6 1.274(4) . ?
N6 O5 1.275(4) . ?

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 C1 N1 123.3(3) . . ?
O1 C1 C5 122.1(3) . . ?
N1 C1 C5 114.6(2) . . ?
N2 C2 C8 119.8(3) . . ?
N2 C2 H2 120.1 . . ?
C8 C2 H2 120.1 . . ?
N3 C3 C4 122.2(3) . . ?
N3 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C3 C4 C5 119.7(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 118.1(3) . . ?
C4 C5 C1 116.7(3) . . ?
C6 C5 C1 125.2(3) . . ?
C7 C6 C5 118.6(3) . . ?
C7 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
N3 C7 C6 123.5(3) . . ?
N3 C7 H7 118.2 . . ?
C6 C7 H7 118.2 . . ?
N4 C8 C9 122.8(3) . . ?
N4 C8 C2 117.4(3) . . ?
C9 C8 C2 119.7(3) . . ?
C10 C9 C8 118.7(3) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C11 C10 C9 119.0(3) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C10 C11 C12 119.0(3) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
N4 C12 C11 123.2(3) . . ?
N4 C12 H12 118.4 . . ?
C11 C12 H12 118.4 . . ?
N3 Cd1 O5 136.28(8) 2_655 . ?
N3 Cd1 N4 112.47(9) 2_655 . ?
O5 Cd1 N4 106.16(8) . . ?
N3 Cd1 O2 81.55(8) 2_655 . ?
O5 Cd1 O2 120.63(8) . . ?
N4 Cd1 O2 87.40(8) . . ?
N3 Cd1 N2 89.61(8) 2_655 . ?
O5 Cd1 N2 84.96(8) . . ?
N4 Cd1 N2 69.85(8) . . ?
O2 Cd1 N2 150.32(8) . . ?
N3 Cd1 O6 96.22(8) 2_655 . ?
O5 Cd1 O6 53.94(8) . . ?
N4 Cd1 O6 148.90(8) . . ?
O2 Cd1 O6 85.12(8) . . ?
N2 Cd1 O6 124.15(8) . . ?
N3 Cd1 O3 130.61(8) 2_655 . ?
O5 Cd1 O3 74.33(7) . . ?
N4 Cd1 O3 80.83(8) . . ?
O2 Cd1 O3 50.66(7) . . ?
N2 Cd1 O3 137.62(8) . . ?
O6 Cd1 O3 71.12(7) . . ?
C1 N1 N2 118.6(2) . . ?
C1 N1 H1A 121(2) . . ?
N2 N1 H1A 120(2) . . ?
C2 N2 N1 116.1(2) . . ?
C2 N2 Cd1 115.70(18) . . ?
N1 N2 Cd1 127.67(18) . . ?
C7 N3 C3 117.8(3) . . ?
C7 N3 Cd1 120.7(2) . 2_645 ?
C3 N3 Cd1 120.5(2) . 2_645 ?
C12 N4 C8 117.3(3) . . ?
C12 N4 Cd1 126.0(2) . . ?
C8 N4 Cd1 116.55(19) . . ?
O4 N5 O3 121.7(3) . . ?
O4 N5 O2 120.5(3) . . ?
O3 N5 O2 117.8(2) . . ?
O7 N6 O6 121.3(3) . . ?
O7 N6 O5 121.2(3) . . ?
O6 N6 O5 117.4(3) . . ?
N5 O2 Cd1 101.38(17) . . ?
N5 O3 Cd1 89.73(16) . . ?
N6 O5 Cd1 96.90(17) . . ?
N6 O6 Cd1 91.53(17) . . ?

_refine_diff_density_max         0.484
_refine_diff_density_min         -0.565
_refine_diff_density_rms         0.086

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 2116314'
_audit_update_record             
;
2021-10-18 deposited with the CCDC.	2022-09-16 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         'C12.89 H14.78 Eu N6 O9, 0.11(H2 O)'
_chemical_formula_sum            'C12.89 H15 Eu N6 O9.11'
_chemical_formula_weight         551.69

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'
Eu Eu -0.1578 3.6682 '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                   19.7262(6)
_cell_length_b                   14.0229(4)
_cell_length_c                   15.5506(4)
_cell_angle_alpha                90
_cell_angle_beta                 116.1130(10)
_cell_angle_gamma                90
_cell_volume                     3862.51(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5908
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      25.37

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.897
_exptl_crystal_F_000             2162
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    3.308
_shelx_estimated_absorpt_T_min   0.504
_shelx_estimated_absorpt_T_max   0.655
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6499
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 2 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11109
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.905
_diffrn_reflns_theta_max         25.374
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             3478
_reflns_number_gt                3006
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0362P)²+29.6836P] 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         3478
_refine_ls_number_parameters     273
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0269
_refine_ls_wR_factor_ref         0.0753
_refine_ls_wR_factor_gt          0.0654
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.032
_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
C1 C 0.6159(2) 0.4673(3) 0.1747(3) 0.0172(9) Uani 1 1 d . . . . .
C2 C 0.8052(3) 0.4463(3) 0.2465(3) 0.0220(10) Uani 1 1 d . . . . .
H2 H 0.8078 0.3910 0.2129 0.026 Uiso 1 1 calc R U . . .
C3 C 0.4088(3) 0.4048(4) 0.0490(4) 0.0305(11) Uani 1 1 d . . . . .
H3 H 0.3646 0.4164 0.0573 0.037 Uiso 1 1 calc R U . . .
C4 C 0.4768(3) 0.4418(4) 0.1161(3) 0.0257(10) Uani 1 1 d . . . . .
H4 H 0.4785 0.4780 0.1687 0.031 Uiso 1 1 calc R U . . .
C5 C 0.5422(2) 0.4252(3) 0.1058(3) 0.0188(9) Uani 1 1 d . . . . .
C6 C 0.5353(3) 0.3731(3) 0.0268(3) 0.0211(10) Uani 1 1 d . . . . .
H6 H 0.5785 0.3610 0.0165 0.025 Uiso 1 1 calc R U . . .
C7 C 0.4657(2) 0.3386(3) -0.0373(3) 0.0211(9) Uani 1 1 d . . . . .
H7 H 0.4624 0.3027 -0.0908 0.025 Uiso 1 1 calc R U . . .
C8 C 0.8736(3) 0.4968(3) 0.3094(3) 0.0225(10) Uani 1 1 d . . . . .
C9 C 0.9439(3) 0.4663(4) 0.3196(4) 0.0290(11) Uani 1 1 d . . . . .
H9 H 0.9483 0.4105 0.2877 0.035 Uiso 1 1 calc R U . . .
C10 C 1.0073(3) 0.5185(4) 0.3770(4) 0.0365(13) Uani 1 1 d . . . . .
H10 H 1.0557 0.5002 0.3834 0.044 Uiso 1 1 calc R U . . .
C11 C 0.9994(3) 0.5975(4) 0.4249(4) 0.0375(13) Uani 1 1 d . . . . .
H11 H 1.0421 0.6347 0.4643 0.045 Uiso 1 1 calc R U . . .
C12 C 0.9274(3) 0.6218(4) 0.4142(4) 0.0309(12) Uani 1 1 d . . . . .
H12 H 0.9225 0.6748 0.4492 0.037 Uiso 1 1 calc R U . . .
Eu1 Eu 0.72806(2) 0.61993(2) 0.32700(2) 0.01514(9) Uani 1 1 d . . . . .
O9 O 0.72397(18) 0.6904(2) 0.1846(2) 0.0236(7) Uani 0.893(10) 1 d . U P A 1
H9A H 0.6815 0.6802 0.1370 0.028 Uiso 0.893(10) 1 d R U P A 1
C13 C 0.7757(3) 0.7407(4) 0.1598(4) 0.0313(15) Uani 0.893(10) 1 d . U P A 1
H13A H 0.7507 0.7577 0.0917 0.047 Uiso 0.893(10) 1 calc R U P A 1
H13B H 0.7924 0.7988 0.1985 0.047 Uiso 0.893(10) 1 calc R U P A 1
H13C H 0.8194 0.7001 0.1721 0.047 Uiso 0.893(10) 1 calc R U P A 1
O9' O 0.72397(18) 0.6904(2) 0.1846(2) 0.0236(7) Uani 0.107(10) 1 d . U P A 2
H9'B H 0.6868 0.6763 0.1340 0.028 Uiso 0.107(10) 1 d R U P A 2
H9'A H 0.7597 0.7232 0.1857 0.028 Uiso 0.107(10) 1 d R U P A 2
O10' O 0.8510(16) 0.740(2) 0.205(2) 0.024(8) Uiso 0.107(10) 1 d . U P A 2
H10A H 0.8479 0.7889 0.1721 0.028 Uiso 0.107(10) 1 d R U P A 2
H10B H 0.8574 0.6961 0.1696 0.028 Uiso 0.107(10) 1 d R U P A 2
N1 N 0.6771(2) 0.4289(3) 0.1742(3) 0.0201(8) Uani 1 1 d . . . . .
N2 N 0.7413(2) 0.4778(3) 0.2373(3) 0.0179(8) Uani 1 1 d . . . . .
N3 N 0.4024(2) 0.3537(3) -0.0268(3) 0.0246(9) Uani 1 1 d . . . . .
N4 N 0.8646(2) 0.5738(3) 0.3568(3) 0.0227(8) Uani 1 1 d . . . . .
N5 N 0.7856(2) 0.5125(3) 0.5057(3) 0.0249(9) Uani 1 1 d . . . . .
N6 N 0.6095(2) 0.7314(3) 0.3488(3) 0.0210(8) Uani 1 1 d . . . . .
O1 O 0.61598(16) 0.5367(2) 0.2277(2) 0.0204(7) Uani 1 1 d . . . . .
O2 O 0.74179(19) 0.4766(2) 0.4240(2) 0.0266(7) Uani 1 1 d . . . . .
O3 O 0.80318(19) 0.5990(2) 0.5063(2) 0.0269(7) Uani 1 1 d . . . . .
O4 O 0.8096(2) 0.4643(3) 0.5789(3) 0.0424(10) Uani 1 1 d . . . . .
O5 O 0.62169(18) 0.7407(2) 0.2760(2) 0.0228(7) Uani 1 1 d . . . . .
O6 O 0.65192(18) 0.6694(2) 0.4118(2) 0.0226(7) Uani 1 1 d . . . . .
O7 O 0.56190(19) 0.7769(3) 0.3609(3) 0.0310(8) Uani 1 1 d . . . . .
O8 O 0.79336(18) 0.7652(2) 0.3953(2) 0.0195(6) Uani 1 1 d D . . . .
H8A H 0.803(3) 0.814(2) 0.374(3) 0.023 Uiso 1 1 d D U . . .
H8B H 0.805(3) 0.778(4) 0.4513(18) 0.023 Uiso 1 1 d D 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
C1 O1 1.273(5) . ?
C1 N1 1.326(6) . ?
C1 C5 1.496(6) . ?
C1 Eu1 3.236(4) . ?
C2 N2 1.282(6) . ?
C2 C8 1.455(6) . ?
C2 H2 0.9500 . ?
C3 N3 1.336(7) . ?
C3 C4 1.386(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(6) . ?
C6 C7 1.381(6) . ?
C6 H6 0.9500 . ?
C7 N3 1.345(6) . ?
C7 H7 0.9500 . ?
C8 N4 1.362(6) . ?
C8 C9 1.392(7) . ?
C9 C10 1.383(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.398(7) . ?
C11 H11 0.9500 . ?
C12 N4 1.346(6) . ?
C12 H12 0.9500 . ?
Eu1 O1 2.373(3) . ?
Eu1 O9' 2.394(3) . ?
Eu1 O9 2.394(3) . ?
Eu1 O8 2.394(3) . ?
Eu1 O2 2.454(3) . ?
Eu1 O6 2.494(3) . ?
Eu1 N2 2.512(4) . ?
Eu1 O3 2.533(3) . ?
Eu1 O5 2.537(3) . ?
Eu1 N4 2.606(4) . ?
Eu1 N5 2.916(4) . ?
Eu1 N6 2.953(4) . ?
Eu1 H9A 2.8102 . ?
O9 C13 1.425(6) . ?
O9 H9A 0.8504 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
O9' H9'B 0.8296 . ?
O9' H9'A 0.8355 . ?
O10' H10A 0.8377 . ?
O10' H10B 0.8793 . ?
N1 N2 1.395(5) . ?
N5 O4 1.226(5) . ?
N5 O3 1.260(5) . ?
N5 O2 1.284(5) . ?
N6 O7 1.217(5) . ?
N6 O5 1.262(5) . ?
N6 O6 1.302(5) . ?
O8 H8A 0.82(2) . ?
O8 H8B 0.817(19) . ?

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 C1 N1 124.9(4) . . ?
O1 C1 C5 119.3(4) . . ?
N1 C1 C5 115.8(4) . . ?
O1 C1 Eu1 38.4(2) . . ?
N1 C1 Eu1 86.7(3) . . ?
C5 C1 Eu1 157.1(3) . . ?
N2 C2 C8 118.9(4) . . ?
N2 C2 H2 120.5 . . ?
C8 C2 H2 120.5 . . ?
N3 C3 C4 123.4(5) . . ?
N3 C3 H3 118.3 . . ?
C4 C3 H3 118.3 . . ?
C3 C4 C5 119.3(4) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 117.2(4) . . ?
C6 C5 C1 122.0(4) . . ?
C4 C5 C1 120.7(4) . . ?
C7 C6 C5 120.2(4) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
N3 C7 C6 122.6(4) . . ?
N3 C7 H7 118.7 . . ?
C6 C7 H7 118.7 . . ?
N4 C8 C9 122.9(4) . . ?
N4 C8 C2 116.4(4) . . ?
C9 C8 C2 120.6(4) . . ?
C10 C9 C8 118.8(5) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C11 C10 C9 119.2(5) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C12 118.7(5) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
N4 C12 C11 123.2(5) . . ?
N4 C12 H12 118.4 . . ?
C11 C12 H12 118.4 . . ?
O1 Eu1 O9' 87.63(11) . . ?
O1 Eu1 O9 87.63(11) . . ?
O1 Eu1 O8 150.76(11) . . ?
O9' Eu1 O8 81.47(11) . . ?
O9 Eu1 O8 81.47(11) . . ?
O1 Eu1 O2 79.42(11) . . ?
O9' Eu1 O2 148.87(11) . . ?
O9 Eu1 O2 148.87(11) . . ?
O8 Eu1 O2 122.11(11) . . ?
O1 Eu1 O6 82.86(10) . . ?
O9' Eu1 O6 126.26(11) . . ?
O9 Eu1 O6 126.26(11) . . ?
O8 Eu1 O6 81.97(11) . . ?
O2 Eu1 O6 80.33(11) . . ?
O1 Eu1 N2 62.80(11) . . ?
O9' Eu1 N2 77.48(11) . . ?
O9 Eu1 N2 77.48(11) . . ?
O8 Eu1 N2 138.97(12) . . ?
O2 Eu1 N2 71.41(12) . . ?
O6 Eu1 N2 138.47(11) . . ?
O1 Eu1 O3 125.84(11) . . ?
O9' Eu1 O3 146.21(11) . . ?
O9 Eu1 O3 146.21(11) . . ?
O8 Eu1 O3 70.75(11) . . ?
O2 Eu1 O3 51.41(11) . . ?
O6 Eu1 O3 69.32(11) . . ?
N2 Eu1 O3 111.46(11) . . ?
O1 Eu1 O5 73.72(10) . . ?
O9' Eu1 O5 75.43(11) . . ?
O9 Eu1 O5 75.43(11) . . ?
O8 Eu1 O5 77.30(11) . . ?
O2 Eu1 O5 126.23(11) . . ?
O6 Eu1 O5 51.10(10) . . ?
N2 Eu1 O5 129.06(11) . . ?
O3 Eu1 O5 115.10(11) . . ?
O1 Eu1 N4 125.97(11) . . ?
O9' Eu1 N4 83.01(12) . . ?
O9 Eu1 N4 83.01(12) . . ?
O8 Eu1 N4 79.66(11) . . ?
O2 Eu1 N4 82.05(12) . . ?
O6 Eu1 N4 142.29(11) . . ?
N2 Eu1 N4 63.21(12) . . ?
O3 Eu1 N4 73.60(12) . . ?
O5 Eu1 N4 150.39(11) . . ?
O1 Eu1 N5 103.09(11) . . ?
O9' Eu1 N5 159.30(11) . . ?
O9 Eu1 N5 159.30(11) . . ?
O8 Eu1 N5 96.25(11) . . ?
O2 Eu1 N5 25.88(11) . . ?
O6 Eu1 N5 73.26(10) . . ?
N2 Eu1 N5 91.57(11) . . ?
O3 Eu1 N5 25.53(11) . . ?
O5 Eu1 N5 124.35(10) . . ?
N4 Eu1 N5 76.36(12) . . ?
O1 Eu1 N6 77.13(10) . . ?
O9' Eu1 N6 100.45(11) . . ?
O9 Eu1 N6 100.45(11) . . ?
O8 Eu1 N6 78.30(11) . . ?
O2 Eu1 N6 103.99(11) . . ?
O6 Eu1 N6 25.95(10) . . ?
N2 Eu1 N6 139.90(11) . . ?
O3 Eu1 N6 92.54(11) . . ?
O5 Eu1 N6 25.15(10) . . ?
N4 Eu1 N6 156.88(11) . . ?
N5 Eu1 N6 99.20(11) . . ?
O1 Eu1 H9A 71.6 . . ?
O9 Eu1 H9A 16.4 . . ?
O8 Eu1 H9A 94.2 . . ?
O2 Eu1 H9A 142.1 . . ?
O6 Eu1 H9A 118.6 . . ?
N2 Eu1 H9A 73.8 . . ?
O3 Eu1 H9A 162.5 . . ?
O5 Eu1 H9A 68.2 . . ?
N4 Eu1 H9A 95.5 . . ?
N5 Eu1 H9A 165.3 . . ?
N6 Eu1 H9A 93.0 . . ?
C13 O9 Eu1 135.9(3) . . ?
C13 O9 H9A 113.3 . . ?
Eu1 O9 H9A 110.7 . . ?
O9 C13 H13A 109.5 . . ?
O9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
Eu1 O9' H9'B 115.7 . . ?
Eu1 O9' H9'A 121.5 . . ?
H9'B O9' H9'A 122.6 . . ?
H10A O10' H10B 100.2 . . ?
C1 N1 N2 110.1(4) . . ?
C2 N2 N1 117.0(4) . . ?
C2 N2 Eu1 123.2(3) . . ?
N1 N2 Eu1 119.7(3) . . ?
C3 N3 C7 117.3(4) . . ?
C12 N4 C8 117.0(4) . . ?
C12 N4 Eu1 124.8(3) . . ?
C8 N4 Eu1 118.2(3) . . ?
O4 N5 O3 122.1(4) . . ?
O4 N5 O2 121.3(4) . . ?
O3 N5 O2 116.6(4) . . ?
O4 N5 Eu1 177.6(3) . . ?
O3 N5 Eu1 60.0(2) . . ?
O2 N5 Eu1 56.6(2) . . ?
O7 N6 O5 123.3(4) . . ?
O7 N6 O6 121.1(4) . . ?
O5 N6 O6 115.6(4) . . ?
O7 N6 Eu1 177.9(3) . . ?
O5 N6 Eu1 58.7(2) . . ?
O6 N6 Eu1 56.95(19) . . ?
C1 O1 Eu1 122.2(3) . . ?
N5 O2 Eu1 97.6(2) . . ?
N5 O3 Eu1 94.4(3) . . ?
N6 O5 Eu1 96.2(2) . . ?
N6 O6 Eu1 97.1(2) . . ?
Eu1 O8 H8A 135(4) . . ?
Eu1 O8 H8B 120(4) . . ?
H8A O8 H8B 105(5) . . ?

_refine_diff_density_max         1.297
_refine_diff_density_min         -1.108
_refine_diff_density_rms         0.122

