# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

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

data_L-H2O
_database_code_depnum_ccdc_archive 'CCDC 2288060'
loop_
_audit_author_name
_audit_author_address
'Chris Hawes'
;Keele University
United Kingdom
;
_audit_update_record             
;
2023-08-10 deposited with the CCDC.	2023-11-01 downloaded from the CCDC.
;
_audit_creation_date             2023-08-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '4(C7 H6 N2 O), 3(H2 O)'
_chemical_formula_sum            'C28 H30 N8 O7'
_chemical_formula_weight         590.60
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   19.0792(8)
_cell_length_b                   7.8359(4)
_cell_length_c                   19.1930(9)
_cell_angle_alpha                90
_cell_angle_beta                 94.0760(10)
_cell_angle_gamma                90
_cell_volume                     2862.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9905
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      30.457
_cell_measurement_theta_min      2.809
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.961
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0621 before and 0.0570 after correction.
The Ratio of minimum to maximum transmission is 0.9267.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            59294
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.561
_diffrn_reflns_theta_min         2.809
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Quest ECO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6199
_reflns_number_total             8783
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     418
_refine_ls_number_reflns         8783
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0501
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0417P)²+0.9836P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1131
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All N(H) groups, All O(H,H) groups
2. Restrained distances
 N3-H3 = N1-H1 = N5-H5A = N7-H7A
 0.88 with sigma of 0.02
 O7-H7B = O7-H7C = O6-H6B = O6-H6A = O5-H5B = O5-H5C
 0.87 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23),
  C26(H26), C27(H27), C28(H28)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O1 O 0.41181(5) 0.04159(13) 0.29149(5) 0.0284(2) Uani 1 1 d . . . . .
N1 N 0.55024(6) 0.16269(15) 0.29328(6) 0.0239(2) Uani 1 1 d D . . . .
H1 H 0.5523(9) 0.0528(19) 0.3078(9) 0.036 Uiso 1 1 d D U . . .
N2 N 0.42522(6) 0.20818(15) 0.28592(6) 0.0236(2) Uani 1 1 d . . . . .
C1 C 0.60751(8) 0.27061(19) 0.29161(7) 0.0276(3) Uani 1 1 d . . . . .
H1A H 0.655166 0.234741 0.296432 0.033 Uiso 1 1 calc R U . . .
C2 C 0.58623(8) 0.43460(19) 0.28213(8) 0.0297(3) Uani 1 1 d . . . . .
H2 H 0.615674 0.531470 0.278412 0.036 Uiso 1 1 calc R U . . .
C3 C 0.51125(8) 0.43422(18) 0.27881(7) 0.0254(3) Uani 1 1 d . . . . .
C4 C 0.49250(7) 0.26184(17) 0.28628(7) 0.0219(3) Uani 1 1 d . . . . .
C5 C 0.45741(8) 0.55529(19) 0.27122(8) 0.0311(3) Uani 1 1 d . . . . .
H5 H 0.467495 0.673046 0.265718 0.037 Uiso 1 1 calc R U . . .
C6 C 0.38912(8) 0.4977(2) 0.27199(8) 0.0327(3) Uani 1 1 d . . . . .
H6 H 0.351660 0.577684 0.267185 0.039 Uiso 1 1 calc R U . . .
C7 C 0.37383(8) 0.3261(2) 0.27960(8) 0.0291(3) Uani 1 1 d . . . . .
H7 H 0.326226 0.291050 0.280366 0.035 Uiso 1 1 calc R U . . .
O2 O 0.56967(5) 0.83468(13) 0.33353(5) 0.0288(2) Uani 1 1 d . . . . .
N3 N 0.45329(6) 0.87242(15) 0.41314(6) 0.0233(2) Uani 1 1 d D . . . .
H3 H 0.4435(9) 0.927(2) 0.3734(8) 0.035 Uiso 1 1 d D U . . .
N4 N 0.57126(6) 0.77701(14) 0.39903(6) 0.0236(2) Uani 1 1 d . . . . .
C8 C 0.40976(8) 0.86335(19) 0.46750(8) 0.0284(3) Uani 1 1 d . . . . .
H8 H 0.363630 0.909403 0.466343 0.034 Uiso 1 1 calc R U . . .
C9 C 0.44194(8) 0.77960(19) 0.52281(8) 0.0300(3) Uani 1 1 d . . . . .
H9 H 0.422530 0.756004 0.566006 0.036 Uiso 1 1 calc R U . . .
C10 C 0.51038(7) 0.73368(17) 0.50388(7) 0.0250(3) Uani 1 1 d . . . . .
C11 C 0.51388(7) 0.79512(16) 0.43544(7) 0.0218(3) Uani 1 1 d . . . . .
C12 C 0.56892(8) 0.64941(19) 0.53486(8) 0.0311(3) Uani 1 1 d . . . . .
H12 H 0.568616 0.604367 0.580793 0.037 Uiso 1 1 calc R U . . .
C13 C 0.62739(8) 0.63326(19) 0.49686(8) 0.0327(3) Uani 1 1 d . . . . .
H13 H 0.667996 0.577374 0.517288 0.039 Uiso 1 1 calc R U . . .
C14 C 0.62801(8) 0.69684(18) 0.42963(8) 0.0296(3) Uani 1 1 d . . . . .
H14 H 0.668938 0.683870 0.404687 0.036 Uiso 1 1 calc R U . . .
O3 O 0.83421(6) 0.64517(13) 0.44145(5) 0.0314(2) Uani 1 1 d . . . . .
N5 N 0.90550(7) 0.60018(15) 0.57285(6) 0.0263(3) Uani 1 1 d D . . . .
H5A H 0.8631(8) 0.555(2) 0.5743(9) 0.039 Uiso 1 1 d D U . . .
N6 N 0.90058(7) 0.69700(14) 0.45372(6) 0.0273(3) Uani 1 1 d . . . . .
C15 C 0.95660(8) 0.6048(2) 0.62740(8) 0.0321(3) Uani 1 1 d . . . . .
H15 H 0.951265 0.560735 0.672830 0.038 Uiso 1 1 calc R U . . .
C16 C 1.01558(8) 0.6814(2) 0.60695(9) 0.0352(3) Uani 1 1 d . . . . .
H16 H 1.057856 0.700386 0.635091 0.042 Uiso 1 1 calc R U . . .
C17 C 1.00237(8) 0.72783(18) 0.53552(8) 0.0302(3) Uani 1 1 d . . . . .
C18 C 0.93314(8) 0.67387(17) 0.51758(7) 0.0256(3) Uani 1 1 d . . . . .
C19 C 1.03825(9) 0.8101(2) 0.48425(9) 0.0366(4) Uani 1 1 d . . . . .
H19 H 1.084876 0.850416 0.493988 0.044 Uiso 1 1 calc R U . . .
C20 C 1.00412(9) 0.8311(2) 0.41910(9) 0.0383(4) Uani 1 1 d . . . . .
H20 H 1.028018 0.885440 0.383425 0.046 Uiso 1 1 calc R U . . .
C21 C 0.93609(9) 0.77514(19) 0.40437(8) 0.0345(3) Uani 1 1 d . . . . .
H21 H 0.913987 0.791813 0.358956 0.041 Uiso 1 1 calc R U . . .
O4 O 0.77545(5) 0.45251(13) 0.58788(5) 0.0272(2) Uani 1 1 d . . . . .
N7 N 0.78883(6) 0.31511(14) 0.45506(6) 0.0232(2) Uani 1 1 d D . . . .
H7A H 0.8017(9) 0.4253(18) 0.4540(9) 0.035 Uiso 1 1 d D U . . .
N8 N 0.77233(6) 0.28398(15) 0.57744(6) 0.0219(2) Uani 1 1 d . . . . .
C22 C 0.79226(8) 0.20081(18) 0.40055(7) 0.0268(3) Uani 1 1 d . . . . .
H22 H 0.799619 0.231596 0.353751 0.032 Uiso 1 1 calc R U . . .
C23 C 0.78366(8) 0.03828(18) 0.42316(7) 0.0271(3) Uani 1 1 d . . . . .
H23 H 0.783289 -0.062179 0.395422 0.033 Uiso 1 1 calc R U . . .
C24 C 0.77527(7) 0.04685(17) 0.49650(7) 0.0228(3) Uani 1 1 d . . . . .
C25 C 0.77862(7) 0.22209(17) 0.51257(7) 0.0202(2) Uani 1 1 d . . . . .
C26 C 0.76761(7) -0.06858(19) 0.55067(8) 0.0278(3) Uani 1 1 d . . . . .
H26 H 0.766888 -0.188191 0.542564 0.033 Uiso 1 1 calc R U . . .
C27 C 0.76111(8) -0.0024(2) 0.61658(8) 0.0312(3) Uani 1 1 d . . . . .
H27 H 0.755470 -0.078328 0.654376 0.037 Uiso 1 1 calc R U . . .
C28 C 0.76258(7) 0.1718(2) 0.62905(7) 0.0278(3) Uani 1 1 d . . . . .
H28 H 0.756612 0.212889 0.674821 0.033 Uiso 1 1 calc R U . . .
O5 O 0.68337(7) 0.85460(16) 0.25653(6) 0.0408(3) Uani 1 1 d D . . . .
H5B H 0.7149(10) 0.780(3) 0.2738(11) 0.061 Uiso 1 1 d D U . . .
H5C H 0.6478(10) 0.853(3) 0.2830(11) 0.061 Uiso 1 1 d D U . . .
O6 O 0.76567(6) 0.61408(16) 0.31502(6) 0.0378(3) Uani 1 1 d D . . . .
H6A H 0.7826(10) 0.534(2) 0.2893(10) 0.057 Uiso 1 1 d D U . . .
H6B H 0.7929(10) 0.626(3) 0.3533(9) 0.057 Uiso 1 1 d D U . . .
O7 O 0.78973(6) 0.59588(15) 0.72202(6) 0.0341(3) Uani 1 1 d D . . . .
H7B H 0.7856(10) 0.549(3) 0.6807(8) 0.051 Uiso 1 1 d D U . . .
H7C H 0.8275(9) 0.553(3) 0.7435(10) 0.051 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
O1 N2 1.3360(15) . ?
N1 H1 0.906(14) . ?
N1 C1 1.3838(18) . ?
N1 C4 1.3469(17) . ?
N2 C4 1.3503(17) . ?
N2 C7 1.3466(18) . ?
C1 H1A 0.9500 . ?
C1 C2 1.356(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.428(2) . ?
C3 C4 1.4073(19) . ?
C3 C5 1.398(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.380(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.386(2) . ?
C7 H7 0.9500 . ?
O2 N4 1.3342(15) . ?
N3 H3 0.882(13) . ?
N3 C8 1.3809(18) . ?
N3 C11 1.3476(17) . ?
N4 C11 1.3474(17) . ?
N4 C14 1.3496(18) . ?
C8 H8 0.9500 . ?
C8 C9 1.357(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.426(2) . ?
C10 C11 1.4050(19) . ?
C10 C12 1.394(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.381(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.384(2) . ?
C14 H14 0.9500 . ?
O3 N6 1.3348(16) . ?
N5 H5A 0.886(14) . ?
N5 C15 1.3794(19) . ?
N5 C18 1.3477(18) . ?
N6 C18 1.3463(19) . ?
N6 C21 1.3499(19) . ?
C15 H15 0.9500 . ?
C15 C16 1.358(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.423(2) . ?
C17 C18 1.406(2) . ?
C17 C19 1.396(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.378(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.380(2) . ?
C21 H21 0.9500 . ?
O4 N8 1.3364(15) . ?
N7 H7A 0.898(14) . ?
N7 C22 1.3824(17) . ?
N7 C25 1.3484(17) . ?
N8 C25 1.3495(17) . ?
N8 C28 1.3469(18) . ?
C22 H22 0.9500 . ?
C22 C23 1.359(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.4296(19) . ?
C24 C25 1.4078(18) . ?
C24 C26 1.3936(19) . ?
C26 H26 0.9500 . ?
C26 C27 1.381(2) . ?
C27 H27 0.9500 . ?
C27 C28 1.386(2) . ?
C28 H28 0.9500 . ?
O5 H5B 0.887(15) . ?
O5 H5C 0.877(16) . ?
O6 H6A 0.873(15) . ?
O6 H6B 0.874(15) . ?
O7 H7B 0.871(15) . ?
O7 H7C 0.872(15) . ?

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
C1 N1 H1 124.8(11) . . ?
C4 N1 H1 126.7(11) . . ?
C4 N1 C1 106.66(12) . . ?
O1 N2 C4 119.43(11) . . ?
O1 N2 C7 122.37(12) . . ?
C7 N2 C4 118.20(12) . . ?
N1 C1 H1A 124.7 . . ?
C2 C1 N1 110.67(13) . . ?
C2 C1 H1A 124.7 . . ?
C1 C2 H2 126.5 . . ?
C1 C2 C3 107.07(13) . . ?
C3 C2 H2 126.5 . . ?
C4 C3 C2 104.99(12) . . ?
C5 C3 C2 136.86(14) . . ?
C5 C3 C4 118.15(13) . . ?
N1 C4 N2 126.25(12) . . ?
N1 C4 C3 110.60(12) . . ?
N2 C4 C3 123.15(12) . . ?
C3 C5 H5 121.2 . . ?
C6 C5 C3 117.66(14) . . ?
C6 C5 H5 121.2 . . ?
C5 C6 H6 119.2 . . ?
C5 C6 C7 121.62(14) . . ?
C7 C6 H6 119.2 . . ?
N2 C7 C6 121.20(14) . . ?
N2 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C8 N3 H3 125.2(11) . . ?
C11 N3 H3 128.0(11) . . ?
C11 N3 C8 106.58(12) . . ?
O2 N4 C11 119.22(11) . . ?
O2 N4 C14 122.11(12) . . ?
C11 N4 C14 118.66(12) . . ?
N3 C8 H8 124.7 . . ?
C9 C8 N3 110.66(13) . . ?
C9 C8 H8 124.7 . . ?
C8 C9 H9 126.4 . . ?
C8 C9 C10 107.11(13) . . ?
C10 C9 H9 126.4 . . ?
C11 C10 C9 104.89(12) . . ?
C12 C10 C9 136.99(14) . . ?
C12 C10 C11 118.12(13) . . ?
N3 C11 C10 110.75(12) . . ?
N4 C11 N3 126.36(12) . . ?
N4 C11 C10 122.90(12) . . ?
C10 C12 H12 121.0 . . ?
C13 C12 C10 118.09(14) . . ?
C13 C12 H12 121.0 . . ?
C12 C13 H13 119.3 . . ?
C12 C13 C14 121.33(14) . . ?
C14 C13 H13 119.3 . . ?
N4 C14 C13 120.90(14) . . ?
N4 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C15 N5 H5A 125.8(12) . . ?
C18 N5 H5A 127.2(12) . . ?
C18 N5 C15 106.93(13) . . ?
O3 N6 C18 119.36(12) . . ?
O3 N6 C21 122.09(13) . . ?
C18 N6 C21 118.54(13) . . ?
N5 C15 H15 124.8 . . ?
C16 C15 N5 110.35(14) . . ?
C16 C15 H15 124.8 . . ?
C15 C16 H16 126.3 . . ?
C15 C16 C17 107.32(14) . . ?
C17 C16 H16 126.3 . . ?
C18 C17 C16 104.95(13) . . ?
C19 C17 C16 137.30(15) . . ?
C19 C17 C18 117.74(15) . . ?
N5 C18 C17 110.44(13) . . ?
N6 C18 N5 126.39(13) . . ?
N6 C18 C17 123.17(13) . . ?
C17 C19 H19 120.9 . . ?
C20 C19 C17 118.10(15) . . ?
C20 C19 H19 120.9 . . ?
C19 C20 H20 119.2 . . ?
C19 C20 C21 121.66(15) . . ?
C21 C20 H20 119.2 . . ?
N6 C21 C20 120.80(15) . . ?
N6 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C22 N7 H7A 125.4(11) . . ?
C25 N7 H7A 126.4(11) . . ?
C25 N7 C22 106.66(11) . . ?
O4 N8 C25 119.17(11) . . ?
O4 N8 C28 122.79(11) . . ?
C28 N8 C25 118.03(12) . . ?
N7 C22 H22 124.7 . . ?
C23 C22 N7 110.62(12) . . ?
C23 C22 H22 124.7 . . ?
C22 C23 H23 126.4 . . ?
C22 C23 C24 107.15(12) . . ?
C24 C23 H23 126.4 . . ?
C25 C24 C23 104.78(12) . . ?
C26 C24 C23 136.81(13) . . ?
C26 C24 C25 118.37(13) . . ?
N7 C25 N8 126.05(12) . . ?
N7 C25 C24 110.79(11) . . ?
N8 C25 C24 123.16(12) . . ?
C24 C26 H26 121.3 . . ?
C27 C26 C24 117.44(14) . . ?
C27 C26 H26 121.3 . . ?
C26 C27 H27 119.1 . . ?
C26 C27 C28 121.73(13) . . ?
C28 C27 H27 119.1 . . ?
N8 C28 C27 121.20(13) . . ?
N8 C28 H28 119.4 . . ?
C27 C28 H28 119.4 . . ?
H5B O5 H5C 108(2) . . ?
H6A O6 H6B 109.2(19) . . ?
H7B O7 H7C 106.7(18) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O2 0.906(14) 1.803(14) 2.7018(15) 171.7(16) 1_545 yes
N3 H3 O1 0.882(13) 1.874(14) 2.7518(15) 173.4(16) 1_565 yes
N5 H5A O4 0.886(14) 1.890(14) 2.7714(16) 173.6(17) . yes
N7 H7A O3 0.898(14) 1.853(14) 2.7457(15) 172.4(16) . yes
O5 H5B O6 0.887(15) 1.773(16) 2.6510(16) 170(2) . yes
O5 H5C O2 0.877(16) 1.840(16) 2.7147(15) 175(2) . yes
O6 H6A O5 0.873(15) 1.805(16) 2.6750(17) 174(2) 2_645 yes
O6 H6B O3 0.874(15) 1.821(16) 2.6843(16) 169(2) . yes
O7 H7B O4 0.871(15) 1.934(15) 2.8044(14) 178(2) . yes
O7 H7C O1 0.872(15) 1.942(15) 2.8145(14) 180(2) 4_666 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N2 C4 N1 -1.46(19) . . . . ?
O1 N2 C4 C3 178.25(12) . . . . ?
O1 N2 C7 C6 -178.21(13) . . . . ?
N1 C1 C2 C3 1.16(17) . . . . ?
C1 N1 C4 N2 -179.27(13) . . . . ?
C1 N1 C4 C3 0.99(15) . . . . ?
C1 C2 C3 C4 -0.52(16) . . . . ?
C1 C2 C3 C5 178.74(16) . . . . ?
C2 C3 C4 N1 -0.31(15) . . . . ?
C2 C3 C4 N2 179.95(12) . . . . ?
C2 C3 C5 C6 -178.80(16) . . . . ?
C3 C5 C6 C7 -0.4(2) . . . . ?
C4 N1 C1 C2 -1.35(16) . . . . ?
C4 N2 C7 C6 1.5(2) . . . . ?
C4 C3 C5 C6 0.4(2) . . . . ?
C5 C3 C4 N1 -179.73(12) . . . . ?
C5 C3 C4 N2 0.5(2) . . . . ?
C5 C6 C7 N2 -0.6(2) . . . . ?
C7 N2 C4 N1 178.83(13) . . . . ?
C7 N2 C4 C3 -1.47(19) . . . . ?
O2 N4 C11 N3 -2.2(2) . . . . ?
O2 N4 C11 C10 178.10(12) . . . . ?
O2 N4 C14 C13 -177.83(13) . . . . ?
N3 C8 C9 C10 0.81(17) . . . . ?
C8 N3 C11 N4 -179.18(13) . . . . ?
C8 N3 C11 C10 0.57(15) . . . . ?
C8 C9 C10 C11 -0.44(15) . . . . ?
C8 C9 C10 C12 179.73(16) . . . . ?
C9 C10 C11 N3 -0.09(15) . . . . ?
C9 C10 C11 N4 179.67(12) . . . . ?
C9 C10 C12 C13 -179.28(15) . . . . ?
C10 C12 C13 C14 -0.7(2) . . . . ?
C11 N3 C8 C9 -0.87(16) . . . . ?
C11 N4 C14 C13 0.4(2) . . . . ?
C11 C10 C12 C13 0.9(2) . . . . ?
C12 C10 C11 N3 179.78(12) . . . . ?
C12 C10 C11 N4 -0.5(2) . . . . ?
C12 C13 C14 N4 0.0(2) . . . . ?
C14 N4 C11 N3 179.50(13) . . . . ?
C14 N4 C11 C10 -0.22(19) . . . . ?
O3 N6 C18 N5 0.5(2) . . . . ?
O3 N6 C18 C17 -178.56(12) . . . . ?
O3 N6 C21 C20 178.40(13) . . . . ?
N5 C15 C16 C17 -0.36(18) . . . . ?
C15 N5 C18 N6 -179.39(13) . . . . ?
C15 N5 C18 C17 -0.20(16) . . . . ?
C15 C16 C17 C18 0.22(17) . . . . ?
C15 C16 C17 C19 178.66(17) . . . . ?
C16 C17 C18 N5 -0.01(16) . . . . ?
C16 C17 C18 N6 179.21(13) . . . . ?
C16 C17 C19 C20 -179.22(17) . . . . ?
C17 C19 C20 C21 0.8(2) . . . . ?
C18 N5 C15 C16 0.35(17) . . . . ?
C18 N6 C21 C20 -0.4(2) . . . . ?
C18 C17 C19 C20 -0.9(2) . . . . ?
C19 C17 C18 N5 -178.81(13) . . . . ?
C19 C17 C18 N6 0.4(2) . . . . ?
C19 C20 C21 N6 -0.2(2) . . . . ?
C21 N6 C18 N5 179.35(13) . . . . ?
C21 N6 C18 C17 0.3(2) . . . . ?
O4 N8 C25 N7 0.78(19) . . . . ?
O4 N8 C25 C24 -179.33(12) . . . . ?
O4 N8 C28 C27 -178.62(13) . . . . ?
N7 C22 C23 C24 -0.93(17) . . . . ?
C22 N7 C25 N8 179.92(13) . . . . ?
C22 N7 C25 C24 0.01(15) . . . . ?
C22 C23 C24 C25 0.89(16) . . . . ?
C22 C23 C24 C26 -176.67(16) . . . . ?
C23 C24 C25 N7 -0.56(15) . . . . ?
C23 C24 C25 N8 179.53(12) . . . . ?
C23 C24 C26 C27 179.71(15) . . . . ?
C24 C26 C27 C28 -0.5(2) . . . . ?
C25 N7 C22 C23 0.58(16) . . . . ?
C25 N8 C28 C27 1.9(2) . . . . ?
C25 C24 C26 C27 2.4(2) . . . . ?
C26 C24 C25 N7 177.54(12) . . . . ?
C26 C24 C25 N8 -2.4(2) . . . . ?
C26 C27 C28 N8 -1.8(2) . . . . ?
C28 N8 C25 N7 -179.71(13) . . . . ?
C28 N8 C25 C24 0.18(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 2288065'
loop_
_audit_author_name
_audit_author_address
'Chris Hawes'
;Keele University
United Kingdom
;
_audit_update_record             
;
2023-08-10 deposited with the CCDC.	2023-11-01 downloaded from the CCDC.
;
_audit_creation_date             2023-08-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'C35 H32 Cl N10 O6 Yb, C21 H18 Cl3 N6 O3 Yb, 2(Cl)'
_chemical_formula_sum            'C56 H50 Cl6 N16 O9 Yb2'
_chemical_formula_weight         1649.90
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'
Yb Yb -0.3850 5.5486 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   13.2616(4)
_cell_length_b                   16.7698(6)
_cell_length_c                   16.9393(6)
_cell_angle_alpha                118.4950(10)
_cell_angle_beta                 93.0430(10)
_cell_angle_gamma                103.0590(10)
_cell_volume                     3167.75(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9852
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      25.74
_cell_measurement_theta_min      2.49
_shelx_estimated_absorpt_T_max   0.881
_shelx_estimated_absorpt_T_min   0.608
_exptl_absorpt_coefficient_mu    3.255
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0705 before and 0.0604 after correction.
The Ratio of minimum to maximum transmission is 0.9101.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1624
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0793
_diffrn_reflns_av_unetI/netI     0.0702
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            62610
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.439
_diffrn_reflns_theta_min         2.446
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Quest ECO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8968
_reflns_number_total             12991
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.140
_refine_diff_density_min         -0.863
_refine_diff_density_rms         0.140
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     827
_refine_ls_number_reflns         12991
_refine_ls_number_restraints     77
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0446
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0197P)²+10.0079P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0743
_refine_ls_wR_factor_ref         0.0852
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 N10-H10 = N2-H2 = N4-H4 = N8-H8 = N6-H6 = N16-H16A = N12-H12 = N14-H14A
 0.88 with sigma of 0.02
3. Rigid body (RIGU) restrains
 N5, N6, C15, C16, C17, C18, C19, C20, C21
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Rotating group:
 O9(H9A,H9B)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3), C6(H6A), C7(H7), C8(H8A), C9(H9), C10(H10A),
 C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C20(H20), C21(H21), C22(H22),
  C23(H23), C24(H24), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31),
 C34(H34), C35(H35), C36(H36), C37(H37), C38(H38), C41(H41), C42(H42), C43(H43),
  C44(H44), C45(H45), C48(H48), C49(H49), C50(H50), C51(H51), C52(H52),
 C55(H55), C56(H56)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Yb1 Yb 0.40941(2) 0.74539(2) 0.14956(2) 0.03148(8) Uani 1 1 d . . . . .
Cl1 Cl 0.36466(17) 0.89408(14) 0.27496(17) 0.0719(7) Uani 1 1 d . . . . .
O1 O 0.3171(3) 0.7457(3) 0.0348(3) 0.0453(13) Uani 1 1 d . . . . .
O2 O 0.5207(3) 0.8350(3) 0.1077(3) 0.0354(11) Uani 1 1 d . . . . .
O3 O 0.5733(3) 0.7909(3) 0.2305(3) 0.0345(10) Uani 1 1 d . . . . .
O4 O 0.4005(3) 0.6754(3) 0.2347(3) 0.0372(11) Uani 1 1 d . . . . .
O5 O 0.2436(3) 0.6551(3) 0.1231(3) 0.0408(12) Uani 1 1 d . . . . .
O9 O 0.4471(3) 0.6146(3) 0.0358(3) 0.0388(11) Uani 1 1 d . . . . .
H9A H 0.417944 0.564660 0.039641 0.058 Uiso 1 1 d R U . . .
H9B H 0.514731 0.621471 0.045715 0.058 Uiso 1 1 d R U . . .
N1 N 0.3510(4) 0.7706(4) -0.0266(4) 0.0395(14) Uani 1 1 d . . . . .
N2 N 0.3310(5) 0.9251(4) 0.0616(4) 0.0377(13) Uani 1 1 d D . . . .
H2 H 0.312(5) 0.921(5) 0.109(3) 0.045 Uiso 1 1 d D U . . .
N3 N 0.6236(4) 0.8815(4) 0.1390(4) 0.0343(13) Uani 1 1 d . . . . .
N4 N 0.5901(5) 1.0174(4) 0.2630(4) 0.0448(15) Uani 1 1 d D . . . .
H4 H 0.5210(17) 1.000(5) 0.250(5) 0.054 Uiso 1 1 d D U . . .
N5 N 0.5966(4) 0.7845(4) 0.3054(4) 0.0499(15) Uani 1 1 d . . . . .
N6 N 0.6624(5) 0.6535(6) 0.2253(5) 0.0623(19) Uani 1 1 d D . . . .
H6 H 0.663(6) 0.648(6) 0.170(3) 0.075 Uiso 1 1 d D U . . .
N7 N 0.3235(4) 0.6565(4) 0.2800(4) 0.0467(15) Uani 1 1 d . . . . .
N8 N 0.3135(5) 0.4937(4) 0.1953(4) 0.0393(14) Uani 1 1 d D . . . .
H8 H 0.360(4) 0.497(5) 0.160(4) 0.047 Uiso 1 1 d D U . . .
N9 N 0.1553(5) 0.6552(4) 0.0784(5) 0.0493(16) Uani 1 1 d . . . . .
N10 N 0.1516(4) 0.5072(4) -0.0488(4) 0.0399(14) Uani 1 1 d D . . . .
H10 H 0.199(4) 0.487(5) -0.030(4) 0.048 Uiso 1 1 d D U . . .
C1 C 0.3796(6) 0.7100(5) -0.1022(5) 0.049(2) Uani 1 1 d . . . . .
H1 H 0.379333 0.649218 -0.112281 0.058 Uiso 1 1 calc R U . . .
C2 C 0.4093(7) 0.7360(6) -0.1655(6) 0.064(2) Uani 1 1 d . . . . .
H2A H 0.429690 0.692599 -0.218648 0.077 Uiso 1 1 calc R U . . .
C3 C 0.4101(6) 0.8233(6) -0.1534(5) 0.058(2) Uani 1 1 d . . . . .
H3 H 0.429417 0.840131 -0.197768 0.070 Uiso 1 1 calc R U . . .
C4 C 0.3819(6) 0.8860(5) -0.0744(5) 0.0428(18) Uani 1 1 d . . . . .
C5 C 0.3542(5) 0.8557(5) -0.0114(5) 0.0366(16) Uani 1 1 d . . . . .
C6 C 0.3706(6) 0.9776(5) -0.0340(5) 0.056(2) Uani 1 1 d . . . . .
H6A H 0.381461 1.017644 -0.059653 0.068 Uiso 1 1 calc R U . . .
C7 C 0.3421(6) 0.9992(5) 0.0463(5) 0.052(2) Uani 1 1 d . . . . .
H7 H 0.331005 1.058139 0.087263 0.062 Uiso 1 1 calc R U . . .
C8 C 0.6974(5) 0.8428(5) 0.0966(5) 0.0361(16) Uani 1 1 d . . . . .
H8A H 0.677103 0.780906 0.044528 0.043 Uiso 1 1 calc R U . . .
C9 C 0.8023(5) 0.8929(5) 0.1286(5) 0.0459(19) Uani 1 1 d . . . . .
H9 H 0.853823 0.865382 0.097777 0.055 Uiso 1 1 calc R U . . .
C10 C 0.8339(5) 0.9819(5) 0.2044(5) 0.0455(18) Uani 1 1 d . . . . .
H10A H 0.906743 1.015025 0.226544 0.055 Uiso 1 1 calc R U . . .
C11 C 0.7599(5) 1.0228(5) 0.2478(5) 0.0406(17) Uani 1 1 d . . . . .
C12 C 0.6537(5) 0.9691(4) 0.2138(5) 0.0332(15) Uani 1 1 d . . . . .
C13 C 0.7560(7) 1.1093(5) 0.3235(5) 0.053(2) Uani 1 1 d . . . . .
H13 H 0.815081 1.161974 0.362130 0.064 Uiso 1 1 calc R U . . .
C14 C 0.6555(7) 1.1042(5) 0.3312(6) 0.058(2) Uani 1 1 d . . . . .
H14 H 0.632057 1.153064 0.376873 0.069 Uiso 1 1 calc R U . . .
C15 C 0.5740(6) 0.8434(6) 0.3872(5) 0.072(2) Uani 1 1 d . . . . .
H15 H 0.544186 0.892081 0.393355 0.086 Uiso 1 1 calc R U . . .
C16 C 0.5959(8) 0.8311(8) 0.4638(6) 0.089(3) Uani 1 1 d . . . . .
H16 H 0.580794 0.871152 0.521553 0.107 Uiso 1 1 calc R U . . .
C17 C 0.6385(8) 0.7608(8) 0.4517(7) 0.097(3) Uani 1 1 d . . . . .
H17 H 0.652615 0.753562 0.503127 0.117 Uiso 1 1 calc R U . . .
C18 C 0.6626(7) 0.7005(8) 0.3729(7) 0.073(2) Uani 1 1 d . . . . .
C19 C 0.6387(6) 0.7152(7) 0.2986(6) 0.0562(19) Uani 1 1 d . . . . .
C20 C 0.7017(7) 0.6225(9) 0.3355(8) 0.095(3) Uani 1 1 d . . . . .
H20 H 0.724556 0.594463 0.367746 0.113 Uiso 1 1 calc R U . . .
C21 C 0.7022(7) 0.5929(8) 0.2464(8) 0.088(3) Uani 1 1 d . . . . .
H21 H 0.724994 0.540766 0.205159 0.105 Uiso 1 1 calc R U . . .
C22 C 0.2876(5) 0.7232(5) 0.3451(5) 0.0396(17) Uani 1 1 d . . . . .
H22 H 0.314113 0.787065 0.359288 0.048 Uiso 1 1 calc R U . . .
C23 C 0.2144(6) 0.7026(5) 0.3914(5) 0.0471(19) Uani 1 1 d . . . . .
H23 H 0.189918 0.751502 0.435880 0.057 Uiso 1 1 calc R U . . .
C24 C 0.1762(5) 0.6116(5) 0.3741(5) 0.0469(19) Uani 1 1 d . . . . .
H24 H 0.126597 0.596191 0.406655 0.056 Uiso 1 1 calc R U . . .
C25 C 0.2132(5) 0.5430(5) 0.3069(5) 0.0363(16) Uani 1 1 d . . . . .
C26 C 0.2864(5) 0.5698(5) 0.2602(5) 0.0406(17) Uani 1 1 d . . . . .
C27 C 0.1956(5) 0.4435(5) 0.2651(5) 0.0440(18) Uani 1 1 d . . . . .
H27 H 0.150202 0.402716 0.280727 0.053 Uiso 1 1 calc R U . . .
C28 C 0.2544(6) 0.4169(5) 0.1995(5) 0.0446(18) Uani 1 1 d . . . . .
H28 H 0.255140 0.353369 0.160970 0.054 Uiso 1 1 calc R U . . .
C29 C 0.1076(5) 0.7254(4) 0.1146(5) 0.0406(17) Uani 1 1 d . . . . .
H29 H 0.138846 0.779431 0.173001 0.049 Uiso 1 1 calc R U . . .
C30 C 0.0161(6) 0.7205(6) 0.0693(6) 0.061(2) Uani 1 1 d . . . . .
H30 H -0.016404 0.769903 0.096323 0.073 Uiso 1 1 calc R U . . .
C31 C -0.0288(6) 0.6428(6) -0.0162(6) 0.064(3) Uani 1 1 d . . . . .
H31 H -0.092476 0.638509 -0.048386 0.077 Uiso 1 1 calc R U . . .
C32 C 0.0185(6) 0.5721(6) -0.0544(6) 0.049(2) Uani 1 1 d . . . . .
C33 C 0.1169(6) 0.5814(5) -0.0011(5) 0.0444(19) Uani 1 1 d . . . . .
C34 C 0.0029(7) 0.4846(6) -0.1356(6) 0.061(2) Uani 1 1 d . . . . .
H34 H -0.053425 0.456798 -0.186221 0.074 Uiso 1 1 calc R U . . .
C35 C 0.0804(6) 0.4471(6) -0.1298(5) 0.057(2) Uani 1 1 d . . . . .
H35 H 0.085593 0.387361 -0.175341 0.069 Uiso 1 1 calc R U . . .
Yb2 Yb 0.80339(2) 0.85044(2) 0.71925(2) 0.02506(7) Uani 1 1 d . . . . .
Cl2 Cl 0.87680(14) 1.03172(11) 0.82105(12) 0.0451(4) Uani 1 1 d . . . . .
Cl3 Cl 0.61196(12) 0.85926(12) 0.69773(12) 0.0406(4) Uani 1 1 d . . . . .
Cl4 Cl 0.78264(13) 0.81775(11) 0.85204(11) 0.0369(4) Uani 1 1 d . . . . .
O6 O 0.7432(3) 0.6971(3) 0.6192(3) 0.0370(11) Uani 1 1 d . . . . .
O7 O 0.8470(4) 0.8651(3) 0.6039(3) 0.0404(11) Uani 1 1 d . . . . .
O8 O 0.9661(3) 0.8389(3) 0.7305(3) 0.0312(10) Uani 1 1 d . . . . .
N11 N 0.6729(4) 0.6214(3) 0.6104(3) 0.0283(12) Uani 1 1 d . . . . .
N12 N 0.7432(4) 0.5174(4) 0.4860(4) 0.0343(13) Uani 1 1 d D . . . .
H12 H 0.795(4) 0.561(3) 0.487(4) 0.041 Uiso 1 1 d D U . . .
N13 N 0.8481(4) 0.9127(4) 0.5620(4) 0.0424(15) Uani 1 1 d . . . . .
N14 N 0.9252(5) 0.8099(4) 0.4425(4) 0.0474(15) Uani 1 1 d D . . . .
H14A H 0.929(6) 0.768(4) 0.462(5) 0.057 Uiso 1 1 d D U . . .
N15 N 1.0144(4) 0.8191(4) 0.7875(4) 0.0343(13) Uani 1 1 d . . . . .
N16 N 1.0151(4) 0.6683(4) 0.6621(4) 0.0399(14) Uani 1 1 d D . . . .
H16A H 0.989(5) 0.679(5) 0.621(4) 0.048 Uiso 1 1 d D U . . .
C36 C 0.5999(5) 0.6269(5) 0.6644(4) 0.0352(16) Uani 1 1 d . . . . .
H36 H 0.596767 0.686990 0.710864 0.042 Uiso 1 1 calc R U . . .
C37 C 0.5306(5) 0.5457(5) 0.6522(5) 0.0425(18) Uani 1 1 d . . . . .
H37 H 0.480839 0.550590 0.691435 0.051 Uiso 1 1 calc R U . . .
C38 C 0.5314(5) 0.4569(5) 0.5840(5) 0.0440(18) Uani 1 1 d . . . . .
H38 H 0.482359 0.401292 0.575560 0.053 Uiso 1 1 calc R U . . .
C39 C 0.6045(5) 0.4516(4) 0.5292(4) 0.0360(16) Uani 1 1 d . . . . .
C40 C 0.6750(5) 0.5354(4) 0.5444(4) 0.0284(14) Uani 1 1 d . . . . .
C41 C 0.6325(6) 0.3779(5) 0.4528(5) 0.049(2) Uani 1 1 d . . . . .
H41 H 0.598567 0.311824 0.423878 0.059 Uiso 1 1 calc R U . . .
C42 C 0.7151(6) 0.4196(5) 0.4302(5) 0.0464(19) Uani 1 1 d . . . . .
H42 H 0.749909 0.386740 0.382399 0.056 Uiso 1 1 calc R U . . .
C43 C 0.8101(6) 0.9876(5) 0.5916(6) 0.052(2) Uani 1 1 d . . . . .
H43 H 0.786160 1.010828 0.648099 0.062 Uiso 1 1 calc R U . . .
C44 C 0.8054(7) 1.0318(6) 0.5402(6) 0.062(2) Uani 1 1 d . . . . .
H44 H 0.776877 1.084016 0.562301 0.075 Uiso 1 1 calc R U . . .
C45 C 0.8422(7) 1.0014(6) 0.4551(6) 0.062(2) Uani 1 1 d . . . . .
H45 H 0.839674 1.032694 0.421128 0.074 Uiso 1 1 calc R U . . .
C46 C 0.8800(6) 0.9268(6) 0.4263(5) 0.052(2) Uani 1 1 d . . . . .
C47 C 0.8844(5) 0.8840(5) 0.4823(5) 0.0417(17) Uani 1 1 d . . . . .
C48 C 0.9271(7) 0.8741(7) 0.3515(5) 0.071(3) Uani 1 1 d . . . . .
H48 H 0.940945 0.886695 0.303547 0.085 Uiso 1 1 calc R U . . .
C49 C 0.9484(7) 0.8043(7) 0.3600(5) 0.063(2) Uani 1 1 d . . . . .
H49 H 0.975692 0.757106 0.316385 0.076 Uiso 1 1 calc R U . . .
C50 C 1.0400(5) 0.8772(5) 0.8774(5) 0.0468(19) Uani 1 1 d . . . . .
H50 H 1.025475 0.936631 0.903671 0.056 Uiso 1 1 calc R U . . .
C51 C 1.0879(6) 0.8519(7) 0.9335(5) 0.062(2) Uani 1 1 d . . . . .
H51 H 1.107195 0.895019 0.997492 0.075 Uiso 1 1 calc R U . . .
C52 C 1.1080(6) 0.7656(8) 0.8980(7) 0.068(3) Uani 1 1 d . . . . .
H52 H 1.138068 0.747755 0.937043 0.081 Uiso 1 1 calc R U . . .
C53 C 1.0837(5) 0.7057(6) 0.8049(6) 0.049(2) Uani 1 1 d . . . . .
C54 C 1.0361(5) 0.7351(5) 0.7511(5) 0.0369(16) Uani 1 1 d . . . . .
C55 C 1.0890(6) 0.6134(7) 0.7401(7) 0.066(3) Uani 1 1 d . . . . .
H55 H 1.116989 0.572890 0.753585 0.080 Uiso 1 1 calc R U . . .
C56 C 1.0476(6) 0.5942(6) 0.6571(7) 0.060(2) Uani 1 1 d . . . . .
H56 H 1.041455 0.536894 0.602034 0.072 Uiso 1 1 calc R U . . .
Cl5 Cl 0.94718(15) 0.64409(14) 0.47042(13) 0.0519(5) Uani 1 1 d . . . . .
Cl6 Cl 0.32992(14) 0.40990(12) -0.01592(13) 0.0489(5) 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
Yb1 Cl1 2.6136(19) . ?
Yb1 O1 2.244(4) . ?
Yb1 O2 2.252(4) . ?
Yb1 O3 2.263(4) . ?
Yb1 O4 2.245(4) . ?
Yb1 O5 2.253(4) . ?
Yb1 O9 2.311(4) . ?
Yb1 H9A 2.7310 . ?
Yb1 H9B 2.7291 . ?
O1 N1 1.355(7) . ?
O2 N3 1.341(6) . ?
O3 N5 1.350(7) . ?
O4 N7 1.379(7) . ?
O5 N9 1.361(7) . ?
O9 H9A 0.8737 . ?
O9 H9B 0.8742 . ?
N1 C1 1.342(8) . ?
N1 C5 1.314(8) . ?
N2 H2 0.88(2) . ?
N2 C5 1.345(8) . ?
N2 C7 1.365(9) . ?
N3 C8 1.347(8) . ?
N3 C12 1.352(8) . ?
N4 H4 0.88(2) . ?
N4 C12 1.341(8) . ?
N4 C14 1.388(9) . ?
N5 C15 1.362(10) . ?
N5 C19 1.359(10) . ?
N6 H6 0.90(2) . ?
N6 C19 1.294(11) . ?
N6 C21 1.419(10) . ?
N7 C22 1.347(8) . ?
N7 C26 1.289(8) . ?
N8 H8 0.89(2) . ?
N8 C26 1.369(8) . ?
N8 C28 1.385(8) . ?
N9 C29 1.361(8) . ?
N9 C33 1.287(9) . ?
N10 H10 0.88(2) . ?
N10 C33 1.324(8) . ?
N10 C35 1.380(9) . ?
C1 H1 0.9500 . ?
C1 C2 1.381(10) . ?
C2 H2A 0.9500 . ?
C2 C3 1.374(11) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(10) . ?
C4 C5 1.415(9) . ?
C4 C6 1.401(10) . ?
C6 H6A 0.9500 . ?
C6 C7 1.329(10) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9500 . ?
C8 C9 1.375(9) . ?
C9 H9 0.9500 . ?
C9 C10 1.373(10) . ?
C10 H10A 0.9500 . ?
C10 C11 1.369(9) . ?
C11 C12 1.405(9) . ?
C11 C13 1.420(10) . ?
C13 H13 0.9500 . ?
C13 C14 1.334(10) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C15 C16 1.433(12) . ?
C16 H16 0.9500 . ?
C16 C17 1.354(15) . ?
C17 H17 0.9500 . ?
C17 C18 1.345(14) . ?
C18 C19 1.426(11) . ?
C18 C20 1.391(14) . ?
C20 H20 0.9500 . ?
C20 C21 1.346(14) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C22 C23 1.366(9) . ?
C23 H23 0.9500 . ?
C23 C24 1.371(9) . ?
C24 H24 0.9500 . ?
C24 C25 1.386(9) . ?
C25 C26 1.414(9) . ?
C25 C27 1.421(9) . ?
C27 H27 0.9500 . ?
C27 C28 1.349(9) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C29 C30 1.365(9) . ?
C30 H30 0.9500 . ?
C30 C31 1.381(11) . ?
C31 H31 0.9500 . ?
C31 C32 1.366(11) . ?
C32 C33 1.480(10) . ?
C32 C34 1.412(11) . ?
C34 H34 0.9500 . ?
C34 C35 1.343(11) . ?
C35 H35 0.9500 . ?
Yb2 Cl2 2.5778(16) . ?
Yb2 Cl3 2.5927(16) . ?
Yb2 Cl4 2.5710(16) . ?
Yb2 O6 2.213(4) . ?
Yb2 O7 2.175(4) . ?
Yb2 O8 2.217(4) . ?
O6 N11 1.332(6) . ?
O7 N13 1.294(6) . ?
O8 N15 1.337(6) . ?
N11 C36 1.354(7) . ?
N11 C40 1.347(7) . ?
N12 H12 0.87(2) . ?
N12 C40 1.350(8) . ?
N12 C42 1.389(8) . ?
N13 C43 1.340(8) . ?
N13 C47 1.357(8) . ?
N14 H14A 0.90(2) . ?
N14 C47 1.354(9) . ?
N14 C49 1.410(9) . ?
N15 C50 1.328(8) . ?
N15 C54 1.349(8) . ?
N16 H16A 0.88(2) . ?
N16 C54 1.344(9) . ?
N16 C56 1.373(9) . ?
C36 H36 0.9500 . ?
C36 C37 1.374(9) . ?
C37 H37 0.9500 . ?
C37 C38 1.385(9) . ?
C38 H38 0.9500 . ?
C38 C39 1.367(9) . ?
C39 C40 1.396(8) . ?
C39 C41 1.439(9) . ?
C41 H41 0.9500 . ?
C41 C42 1.338(10) . ?
C42 H42 0.9500 . ?
C43 H43 0.9500 . ?
C43 C44 1.393(10) . ?
C44 H44 0.9500 . ?
C44 C45 1.435(11) . ?
C45 H45 0.9500 . ?
C45 C46 1.335(11) . ?
C46 C47 1.442(10) . ?
C46 C48 1.429(11) . ?
C48 H48 0.9500 . ?
C48 C49 1.332(11) . ?
C49 H49 0.9500 . ?
C50 H50 0.9500 . ?
C50 C51 1.388(10) . ?
C51 H51 0.9500 . ?
C51 C52 1.373(12) . ?
C52 H52 0.9500 . ?
C52 C53 1.374(12) . ?
C53 C54 1.408(9) . ?
C53 C55 1.430(11) . ?
C55 H55 0.9500 . ?
C55 C56 1.337(11) . ?
C56 H56 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Yb1 H9A 163.3 . . ?
Cl1 Yb1 H9B 163.2 . . ?
O1 Yb1 Cl1 93.10(14) . . ?
O1 Yb1 O2 72.76(15) . . ?
O1 Yb1 O3 143.72(15) . . ?
O1 Yb1 O4 142.55(15) . . ?
O1 Yb1 O5 72.98(15) . . ?
O1 Yb1 O9 85.42(16) . . ?
O1 Yb1 H9A 92.7 . . ?
O1 Yb1 H9B 97.2 . . ?
O2 Yb1 Cl1 91.29(12) . . ?
O2 Yb1 O3 71.23(15) . . ?
O2 Yb1 O5 145.74(15) . . ?
O2 Yb1 O9 88.02(15) . . ?
O2 Yb1 H9A 105.4 . . ?
O2 Yb1 H9B 79.2 . . ?
O3 Yb1 Cl1 91.98(12) . . ?
O3 Yb1 O9 89.07(15) . . ?
O3 Yb1 H9A 92.6 . . ?
O3 Yb1 H9B 71.9 . . ?
O4 Yb1 Cl1 93.43(13) . . ?
O4 Yb1 O2 143.80(15) . . ?
O4 Yb1 O3 72.75(15) . . ?
O4 Yb1 O5 70.09(15) . . ?
O4 Yb1 O9 87.91(16) . . ?
O4 Yb1 H9A 72.6 . . ?
O4 Yb1 H9B 86.5 . . ?
O5 Yb1 Cl1 90.81(13) . . ?
O5 Yb1 O3 142.83(15) . . ?
O5 Yb1 O9 89.00(16) . . ?
O5 Yb1 H9A 75.9 . . ?
O5 Yb1 H9B 104.9 . . ?
O9 Yb1 Cl1 178.49(12) . . ?
O9 Yb1 H9A 17.5 . . ?
O9 Yb1 H9B 17.6 . . ?
H9A Yb1 H9B 29.3 . . ?
N1 O1 Yb1 130.1(3) . . ?
N3 O2 Yb1 130.9(3) . . ?
N5 O3 Yb1 125.3(3) . . ?
N7 O4 Yb1 131.5(4) . . ?
N9 O5 Yb1 127.1(3) . . ?
Yb1 O9 H9A 109.6 . . ?
Yb1 O9 H9B 109.4 . . ?
H9A O9 H9B 104.3 . . ?
C1 N1 O1 121.5(6) . . ?
C5 N1 O1 118.6(6) . . ?
C5 N1 C1 119.9(6) . . ?
C5 N2 H2 125(4) . . ?
C5 N2 C7 106.6(6) . . ?
C7 N2 H2 128(4) . . ?
O2 N3 C8 121.1(5) . . ?
O2 N3 C12 119.5(5) . . ?
C8 N3 C12 119.4(6) . . ?
C12 N4 H4 126(5) . . ?
C12 N4 C14 106.1(6) . . ?
C14 N4 H4 127(5) . . ?
O3 N5 C15 121.3(7) . . ?
O3 N5 C19 119.6(6) . . ?
C19 N5 C15 119.1(8) . . ?
C19 N6 H6 132(5) . . ?
C19 N6 C21 108.1(8) . . ?
C21 N6 H6 120(5) . . ?
C22 N7 O4 123.9(6) . . ?
C26 N7 O4 117.4(6) . . ?
C26 N7 C22 118.6(6) . . ?
C26 N8 H8 125(4) . . ?
C26 N8 C28 104.8(6) . . ?
C28 N8 H8 130(4) . . ?
O5 N9 C29 123.7(6) . . ?
C33 N9 O5 114.9(6) . . ?
C33 N9 C29 121.4(7) . . ?
C33 N10 H10 129(5) . . ?
C33 N10 C35 107.8(7) . . ?
C35 N10 H10 121(5) . . ?
N1 C1 H1 119.9 . . ?
N1 C1 C2 120.1(7) . . ?
C2 C1 H1 119.9 . . ?
C1 C2 H2A 119.3 . . ?
C3 C2 C1 121.5(7) . . ?
C3 C2 H2A 119.3 . . ?
C2 C3 H3 120.9 . . ?
C2 C3 C4 118.1(7) . . ?
C4 C3 H3 120.9 . . ?
C3 C4 C5 117.6(7) . . ?
C3 C4 C6 138.4(7) . . ?
C6 C4 C5 104.0(6) . . ?
N1 C5 N2 127.3(6) . . ?
N1 C5 C4 122.7(6) . . ?
N2 C5 C4 110.0(6) . . ?
C4 C6 H6A 125.6 . . ?
C7 C6 C4 108.7(7) . . ?
C7 C6 H6A 125.6 . . ?
N2 C7 H7 124.6 . . ?
C6 C7 N2 110.7(7) . . ?
C6 C7 H7 124.6 . . ?
N3 C8 H8A 120.0 . . ?
N3 C8 C9 120.0(6) . . ?
C9 C8 H8A 120.0 . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.2(7) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10A 120.2 . . ?
C11 C10 C9 119.7(7) . . ?
C11 C10 H10A 120.2 . . ?
C10 C11 C12 117.5(7) . . ?
C10 C11 C13 138.6(7) . . ?
C12 C11 C13 103.8(6) . . ?
N3 C12 C11 122.2(6) . . ?
N4 C12 N3 126.6(6) . . ?
N4 C12 C11 111.2(6) . . ?
C11 C13 H13 125.8 . . ?
C14 C13 C11 108.5(7) . . ?
C14 C13 H13 125.8 . . ?
N4 C14 H14 124.8 . . ?
C13 C14 N4 110.3(7) . . ?
C13 C14 H14 124.8 . . ?
N5 C15 H15 120.4 . . ?
N5 C15 C16 119.2(10) . . ?
C16 C15 H15 120.4 . . ?
C15 C16 H16 120.9 . . ?
C17 C16 C15 118.3(11) . . ?
C17 C16 H16 120.9 . . ?
C16 C17 H17 117.3 . . ?
C18 C17 C16 125.4(11) . . ?
C18 C17 H17 117.3 . . ?
C17 C18 C19 114.3(11) . . ?
C17 C18 C20 141.1(10) . . ?
C20 C18 C19 104.6(10) . . ?
N5 C19 C18 123.9(9) . . ?
N6 C19 N5 125.7(7) . . ?
N6 C19 C18 110.4(9) . . ?
C18 C20 H20 125.3 . . ?
C21 C20 C18 109.3(9) . . ?
C21 C20 H20 125.3 . . ?
N6 C21 H21 126.2 . . ?
C20 C21 N6 107.6(10) . . ?
C20 C21 H21 126.2 . . ?
N7 C22 H22 118.8 . . ?
N7 C22 C23 122.5(6) . . ?
C23 C22 H22 118.8 . . ?
C22 C23 H23 119.9 . . ?
C22 C23 C24 120.3(7) . . ?
C24 C23 H23 119.9 . . ?
C23 C24 H24 121.4 . . ?
C23 C24 C25 117.2(6) . . ?
C25 C24 H24 121.4 . . ?
C24 C25 C26 119.0(7) . . ?
C24 C25 C27 137.2(6) . . ?
C26 C25 C27 103.8(6) . . ?
N7 C26 N8 125.9(7) . . ?
N7 C26 C25 122.4(7) . . ?
N8 C26 C25 111.7(6) . . ?
C25 C27 H27 125.9 . . ?
C28 C27 C25 108.3(6) . . ?
C28 C27 H27 125.9 . . ?
N8 C28 H28 124.2 . . ?
C27 C28 N8 111.5(6) . . ?
C27 C28 H28 124.2 . . ?
N9 C29 H29 119.1 . . ?
N9 C29 C30 121.8(7) . . ?
C30 C29 H29 119.1 . . ?
C29 C30 H30 120.4 . . ?
C29 C30 C31 119.3(8) . . ?
C31 C30 H30 120.4 . . ?
C30 C31 H31 120.0 . . ?
C32 C31 C30 119.9(7) . . ?
C32 C31 H31 120.0 . . ?
C31 C32 C33 118.0(8) . . ?
C31 C32 C34 139.2(8) . . ?
C34 C32 C33 102.8(7) . . ?
N9 C33 N10 130.8(8) . . ?
N9 C33 C32 119.6(7) . . ?
N10 C33 C32 109.6(7) . . ?
C32 C34 H34 125.5 . . ?
C35 C34 C32 109.0(7) . . ?
C35 C34 H34 125.5 . . ?
N10 C35 H35 124.6 . . ?
C34 C35 N10 110.8(7) . . ?
C34 C35 H35 124.6 . . ?
Cl2 Yb2 Cl3 92.41(6) . . ?
Cl4 Yb2 Cl2 95.61(6) . . ?
Cl4 Yb2 Cl3 93.99(5) . . ?
O6 Yb2 Cl2 173.82(12) . . ?
O6 Yb2 Cl3 87.58(12) . . ?
O6 Yb2 Cl4 90.55(12) . . ?
O6 Yb2 O8 90.55(15) . . ?
O7 Yb2 Cl2 88.27(13) . . ?
O7 Yb2 Cl3 96.81(13) . . ?
O7 Yb2 Cl4 168.36(13) . . ?
O7 Yb2 O6 85.60(16) . . ?
O7 Yb2 O8 81.10(16) . . ?
O8 Yb2 Cl2 89.23(11) . . ?
O8 Yb2 Cl3 177.30(11) . . ?
O8 Yb2 Cl4 87.98(11) . . ?
N11 O6 Yb2 138.0(3) . . ?
N13 O7 Yb2 146.1(4) . . ?
N15 O8 Yb2 127.9(3) . . ?
O6 N11 C36 123.3(5) . . ?
O6 N11 C40 117.9(5) . . ?
C40 N11 C36 118.8(5) . . ?
C40 N12 H12 124(4) . . ?
C40 N12 C42 106.0(6) . . ?
C42 N12 H12 130(4) . . ?
O7 N13 C43 122.9(6) . . ?
O7 N13 C47 119.5(6) . . ?
C43 N13 C47 117.5(6) . . ?
C47 N14 H14A 127(5) . . ?
C47 N14 C49 105.7(7) . . ?
C49 N14 H14A 127(5) . . ?
O8 N15 C54 117.7(5) . . ?
C50 N15 O8 123.3(6) . . ?
C50 N15 C54 119.1(6) . . ?
C54 N16 H16A 120(5) . . ?
C54 N16 C56 106.5(7) . . ?
C56 N16 H16A 134(5) . . ?
N11 C36 H36 119.9 . . ?
N11 C36 C37 120.1(6) . . ?
C37 C36 H36 119.9 . . ?
C36 C37 H37 119.2 . . ?
C36 C37 C38 121.6(6) . . ?
C38 C37 H37 119.2 . . ?
C37 C38 H38 120.9 . . ?
C39 C38 C37 118.2(6) . . ?
C39 C38 H38 120.9 . . ?
C38 C39 C40 118.8(6) . . ?
C38 C39 C41 136.7(7) . . ?
C40 C39 C41 104.5(6) . . ?
N11 C40 N12 126.3(6) . . ?
N11 C40 C39 122.5(6) . . ?
N12 C40 C39 111.2(5) . . ?
C39 C41 H41 126.4 . . ?
C42 C41 C39 107.3(6) . . ?
C42 C41 H41 126.4 . . ?
N12 C42 H42 124.5 . . ?
C41 C42 N12 111.0(6) . . ?
C41 C42 H42 124.5 . . ?
N13 C43 H43 119.7 . . ?
N13 C43 C44 120.7(7) . . ?
C44 C43 H43 119.7 . . ?
C43 C44 H44 118.8 . . ?
C43 C44 C45 122.4(8) . . ?
C45 C44 H44 118.8 . . ?
C44 C45 H45 121.8 . . ?
C46 C45 C44 116.4(7) . . ?
C46 C45 H45 121.8 . . ?
C45 C46 C47 119.1(7) . . ?
C45 C46 C48 137.3(8) . . ?
C48 C46 C47 103.4(7) . . ?
N13 C47 C46 123.8(7) . . ?
N14 C47 N13 125.4(6) . . ?
N14 C47 C46 110.8(6) . . ?
C46 C48 H48 125.5 . . ?
C49 C48 C46 109.0(7) . . ?
C49 C48 H48 125.5 . . ?
N14 C49 H49 124.6 . . ?
C48 C49 N14 110.9(7) . . ?
C48 C49 H49 124.6 . . ?
N15 C50 H50 119.6 . . ?
N15 C50 C51 120.7(7) . . ?
C51 C50 H50 119.6 . . ?
C50 C51 H51 119.5 . . ?
C52 C51 C50 121.1(8) . . ?
C52 C51 H51 119.5 . . ?
C51 C52 H52 120.6 . . ?
C51 C52 C53 118.7(8) . . ?
C53 C52 H52 120.6 . . ?
C52 C53 C54 117.8(8) . . ?
C52 C53 C55 138.2(8) . . ?
C54 C53 C55 104.0(7) . . ?
N15 C54 C53 122.5(7) . . ?
N16 C54 N15 126.7(6) . . ?
N16 C54 C53 110.8(7) . . ?
C53 C55 H55 126.2 . . ?
C56 C55 C53 107.7(7) . . ?
C56 C55 H55 126.2 . . ?
N16 C56 H56 124.5 . . ?
C55 C56 N16 111.0(8) . . ?
C55 C56 H56 124.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O9 H9A Cl6 0.87 2.27 3.089(5) 155.3 . yes
O9 H9B Cl6 0.87 2.26 3.090(5) 157.6 2_665 yes
N4 H4 Cl1 0.88(2) 2.60(5) 3.306(6) 138(6) . yes
N6 H6 Cl6 0.90(2) 2.33(3) 3.194(8) 163(7) 2_665 yes
N8 H8 Cl6 0.89(2) 2.58(5) 3.202(6) 128(5) . yes
N10 H10 Cl6 0.88(2) 2.46(3) 3.322(6) 167(6) . yes
C10 H10A O8 0.95 2.38 3.194(8) 143.2 2_776 yes
N12 H12 Cl5 0.87(2) 2.30(3) 3.148(6) 165(6) . yes
N14 H14A Cl5 0.90(2) 2.23(3) 3.107(7) 164(6) . yes
N16 H16A Cl5 0.88(2) 2.33(4) 3.128(7) 152(6) . yes
C52 H52 N1 0.95 2.76 3.371(9) 123.1 1_656 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Yb1 O1 N1 C1 82.6(7) . . . . ?
Yb1 O1 N1 C5 -98.3(6) . . . . ?
Yb1 O2 N3 C8 96.6(6) . . . . ?
Yb1 O2 N3 C12 -84.2(6) . . . . ?
Yb1 O3 N5 C15 -72.5(7) . . . . ?
Yb1 O3 N5 C19 104.3(6) . . . . ?
Yb1 O4 N7 C22 -58.2(8) . . . . ?
Yb1 O4 N7 C26 124.0(5) . . . . ?
Yb1 O5 N9 C29 -73.6(7) . . . . ?
Yb1 O5 N9 C33 108.4(6) . . . . ?
O1 N1 C1 C2 177.1(7) . . . . ?
O1 N1 C5 N2 2.7(10) . . . . ?
O1 N1 C5 C4 -175.8(6) . . . . ?
O2 N3 C8 C9 178.3(6) . . . . ?
O2 N3 C12 N4 0.3(9) . . . . ?
O2 N3 C12 C11 -177.5(5) . . . . ?
O3 N5 C15 C16 177.2(6) . . . . ?
O3 N5 C19 N6 1.9(11) . . . . ?
O3 N5 C19 C18 -177.7(6) . . . . ?
O4 N7 C22 C23 -177.1(6) . . . . ?
O4 N7 C26 N8 -2.8(10) . . . . ?
O4 N7 C26 C25 175.1(5) . . . . ?
O5 N9 C29 C30 -176.6(6) . . . . ?
O5 N9 C33 N10 -3.5(10) . . . . ?
O5 N9 C33 C32 177.6(5) . . . . ?
N1 C1 C2 C3 -0.3(13) . . . . ?
N3 C8 C9 C10 0.8(10) . . . . ?
N5 C15 C16 C17 0.1(13) . . . . ?
N7 C22 C23 C24 1.5(12) . . . . ?
N9 C29 C30 C31 -1.0(11) . . . . ?
C1 N1 C5 N2 -178.1(7) . . . . ?
C1 N1 C5 C4 3.3(10) . . . . ?
C1 C2 C3 C4 1.2(13) . . . . ?
C2 C3 C4 C5 0.1(11) . . . . ?
C2 C3 C4 C6 -179.4(9) . . . . ?
C3 C4 C5 N1 -2.4(11) . . . . ?
C3 C4 C5 N2 178.9(6) . . . . ?
C3 C4 C6 C7 -178.7(9) . . . . ?
C4 C6 C7 N2 -1.4(10) . . . . ?
C5 N1 C1 C2 -2.0(11) . . . . ?
C5 N2 C7 C6 0.4(9) . . . . ?
C5 C4 C6 C7 1.7(9) . . . . ?
C6 C4 C5 N1 177.3(7) . . . . ?
C6 C4 C5 N2 -1.5(8) . . . . ?
C7 N2 C5 N1 -178.0(7) . . . . ?
C7 N2 C5 C4 0.7(8) . . . . ?
C8 N3 C12 N4 179.5(6) . . . . ?
C8 N3 C12 C11 1.7(9) . . . . ?
C8 C9 C10 C11 -1.5(11) . . . . ?
C9 C10 C11 C12 2.2(10) . . . . ?
C9 C10 C11 C13 -178.8(8) . . . . ?
C10 C11 C12 N3 -2.4(10) . . . . ?
C10 C11 C12 N4 179.6(6) . . . . ?
C10 C11 C13 C14 -179.0(8) . . . . ?
C11 C13 C14 N4 -0.4(9) . . . . ?
C12 N3 C8 C9 -0.9(9) . . . . ?
C12 N4 C14 C13 0.6(9) . . . . ?
C12 C11 C13 C14 0.1(8) . . . . ?
C13 C11 C12 N3 178.3(6) . . . . ?
C13 C11 C12 N4 0.2(8) . . . . ?
C14 N4 C12 N3 -178.5(6) . . . . ?
C14 N4 C12 C11 -0.5(8) . . . . ?
C15 N5 C19 N6 178.8(7) . . . . ?
C15 N5 C19 C18 -0.8(10) . . . . ?
C15 C16 C17 C18 -0.1(16) . . . . ?
C16 C17 C18 C19 -0.4(14) . . . . ?
C16 C17 C18 C20 -177.4(12) . . . . ?
C17 C18 C19 N5 0.8(11) . . . . ?
C17 C18 C19 N6 -178.9(8) . . . . ?
C17 C18 C20 C21 177.6(11) . . . . ?
C18 C20 C21 N6 0.1(11) . . . . ?
C19 N5 C15 C16 0.3(10) . . . . ?
C19 N6 C21 C20 -0.6(10) . . . . ?
C19 C18 C20 C21 0.4(11) . . . . ?
C20 C18 C19 N5 178.9(7) . . . . ?
C20 C18 C19 N6 -0.8(9) . . . . ?
C21 N6 C19 N5 -178.8(7) . . . . ?
C21 N6 C19 C18 0.9(9) . . . . ?
C22 N7 C26 N8 179.2(6) . . . . ?
C22 N7 C26 C25 -2.8(10) . . . . ?
C22 C23 C24 C25 -1.5(11) . . . . ?
C23 C24 C25 C26 -0.5(10) . . . . ?
C23 C24 C25 C27 -178.0(8) . . . . ?
C24 C25 C26 N7 2.7(10) . . . . ?
C24 C25 C26 N8 -179.0(6) . . . . ?
C24 C25 C27 C28 177.5(8) . . . . ?
C25 C27 C28 N8 1.3(8) . . . . ?
C26 N7 C22 C23 0.8(11) . . . . ?
C26 N8 C28 C27 -1.7(8) . . . . ?
C26 C25 C27 C28 -0.3(7) . . . . ?
C27 C25 C26 N7 -179.0(6) . . . . ?
C27 C25 C26 N8 -0.7(7) . . . . ?
C28 N8 C26 N7 179.6(7) . . . . ?
C28 N8 C26 C25 1.5(7) . . . . ?
C29 N9 C33 N10 178.5(7) . . . . ?
C29 N9 C33 C32 -0.4(10) . . . . ?
C29 C30 C31 C32 0.0(12) . . . . ?
C30 C31 C32 C33 0.7(11) . . . . ?
C30 C31 C32 C34 -179.5(9) . . . . ?
C31 C32 C33 N9 -0.5(10) . . . . ?
C31 C32 C33 N10 -179.7(6) . . . . ?
C31 C32 C34 C35 -178.8(9) . . . . ?
C32 C34 C35 N10 -2.2(9) . . . . ?
C33 N9 C29 C30 1.2(10) . . . . ?
C33 N10 C35 C34 2.5(9) . . . . ?
C33 C32 C34 C35 1.0(8) . . . . ?
C34 C32 C33 N9 179.6(6) . . . . ?
C34 C32 C33 N10 0.5(8) . . . . ?
C35 N10 C33 N9 179.2(7) . . . . ?
C35 N10 C33 C32 -1.8(8) . . . . ?
Yb2 O6 N11 C36 12.6(9) . . . . ?
Yb2 O6 N11 C40 -167.4(4) . . . . ?
Yb2 O7 N13 C43 0.2(12) . . . . ?
Yb2 O7 N13 C47 -176.5(5) . . . . ?
Yb2 O8 N15 C50 -67.6(7) . . . . ?
Yb2 O8 N15 C54 111.4(5) . . . . ?
O6 N11 C36 C37 -179.2(6) . . . . ?
O6 N11 C40 N12 1.1(9) . . . . ?
O6 N11 C40 C39 -179.8(6) . . . . ?
O7 N13 C43 C44 -174.8(7) . . . . ?
O7 N13 C47 N14 -2.9(11) . . . . ?
O7 N13 C47 C46 174.1(6) . . . . ?
O8 N15 C50 C51 178.5(6) . . . . ?
O8 N15 C54 N16 0.7(9) . . . . ?
O8 N15 C54 C53 -178.0(5) . . . . ?
N11 C36 C37 C38 -1.4(11) . . . . ?
N13 C43 C44 C45 -1.2(13) . . . . ?
N15 C50 C51 C52 -1.4(11) . . . . ?
C36 N11 C40 N12 -178.9(6) . . . . ?
C36 N11 C40 C39 0.3(9) . . . . ?
C36 C37 C38 C39 0.9(11) . . . . ?
C37 C38 C39 C40 0.1(10) . . . . ?
C37 C38 C39 C41 -179.4(8) . . . . ?
C38 C39 C40 N11 -0.7(10) . . . . ?
C38 C39 C40 N12 178.6(6) . . . . ?
C38 C39 C41 C42 -178.7(8) . . . . ?
C39 C41 C42 N12 -1.1(9) . . . . ?
C40 N11 C36 C37 0.8(9) . . . . ?
C40 N12 C42 C41 0.0(8) . . . . ?
C40 C39 C41 C42 1.7(8) . . . . ?
C41 C39 C40 N11 179.0(6) . . . . ?
C41 C39 C40 N12 -1.8(7) . . . . ?
C42 N12 C40 N11 -179.6(6) . . . . ?
C42 N12 C40 C39 1.1(7) . . . . ?
C43 N13 C47 N14 -179.9(7) . . . . ?
C43 N13 C47 C46 -2.9(11) . . . . ?
C43 C44 C45 C46 1.1(12) . . . . ?
C44 C45 C46 C47 -1.8(11) . . . . ?
C44 C45 C46 C48 -177.3(9) . . . . ?
C45 C46 C47 N13 2.9(11) . . . . ?
C45 C46 C47 N14 -179.8(7) . . . . ?
C45 C46 C48 C49 -179.7(10) . . . . ?
C46 C48 C49 N14 -4.4(11) . . . . ?
C47 N13 C43 C44 2.0(11) . . . . ?
C47 N14 C49 C48 2.5(9) . . . . ?
C47 C46 C48 C49 4.4(10) . . . . ?
C48 C46 C47 N13 179.7(7) . . . . ?
C48 C46 C47 N14 -2.9(8) . . . . ?
C49 N14 C47 N13 177.8(7) . . . . ?
C49 N14 C47 C46 0.4(8) . . . . ?
C50 N15 C54 N16 179.7(6) . . . . ?
C50 N15 C54 C53 1.0(9) . . . . ?
C50 C51 C52 C53 2.7(12) . . . . ?
C51 C52 C53 C54 -2.1(11) . . . . ?
C51 C52 C53 C55 -179.2(8) . . . . ?
C52 C53 C54 N15 0.3(10) . . . . ?
C52 C53 C54 N16 -178.6(6) . . . . ?
C52 C53 C55 C56 177.6(9) . . . . ?
C53 C55 C56 N16 0.3(9) . . . . ?
C54 N15 C50 C51 -0.4(10) . . . . ?
C54 N16 C56 C55 -0.6(8) . . . . ?
C54 C53 C55 C56 0.2(8) . . . . ?
C55 C53 C54 N15 178.3(6) . . . . ?
C55 C53 C54 N16 -0.6(7) . . . . ?
C56 N16 C54 N15 -178.1(6) . . . . ?
C56 N16 C54 C53 0.7(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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 2288061'
loop_
_audit_author_name
_audit_author_address
'Chris Hawes'
;Keele University
United Kingdom
;
_audit_update_record             
;
2023-08-10 deposited with the CCDC.	2023-11-01 downloaded from the CCDC.
;
_audit_creation_date             2023-08-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H10 Cu N4 O2'
_chemical_formula_sum            'C14 H10 Cu N4 O2'
_chemical_formula_weight         329.80
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   8.6982(5)
_cell_length_b                   11.0452(6)
_cell_length_c                   13.7542(8)
_cell_angle_alpha                90
_cell_angle_beta                 106.867(2)
_cell_angle_gamma                90
_cell_volume                     1264.57(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4840
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      27.477
_cell_measurement_theta_min      3.064
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.745
_exptl_absorpt_coefficient_mu    1.737
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6447
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0683 before and 0.0585 after correction.
The Ratio of minimum to maximum transmission is 0.8647.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.732
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             668
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.534
_diffrn_reflns_theta_min         3.064
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Quest ECO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2173
_reflns_number_total             2911
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2911
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0403
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0339P)²+1.2299P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0892
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13),
 C14(H14)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.43361(4) 0.38673(3) 0.55715(3) 0.02255(12) Uani 1 1 d . . . . .
O1 O 0.5389(3) 0.28150(19) 0.67588(17) 0.0319(5) Uani 1 1 d . . . . .
O2 O 0.3159(2) 0.48615(18) 0.43587(16) 0.0254(5) Uani 1 1 d . . . . .
N1 N 0.5023(3) 0.2664(2) 0.4782(2) 0.0263(6) Uani 1 1 d . . . . .
N2 N 0.6079(3) 0.1876(2) 0.6421(2) 0.0283(6) Uani 1 1 d . . . . .
N3 N 0.3298(3) 0.4926(2) 0.6307(2) 0.0256(6) Uani 1 1 d . . . . .
N4 N 0.2105(3) 0.5586(2) 0.4644(2) 0.0251(6) Uani 1 1 d . . . . .
C1 C 0.5156(4) 0.2322(3) 0.3855(3) 0.0314(7) Uani 1 1 d . . . . .
H1 H 0.467465 0.274719 0.324173 0.038 Uiso 1 1 calc R U . . .
C2 C 0.6075(4) 0.1285(3) 0.3913(3) 0.0338(8) Uani 1 1 d . . . . .
H2 H 0.632736 0.088742 0.336613 0.041 Uiso 1 1 calc R U . . .
C3 C 0.6560(4) 0.0936(3) 0.4944(3) 0.0341(8) Uani 1 1 d . . . . .
C4 C 0.5882(3) 0.1822(3) 0.5424(3) 0.0251(7) Uani 1 1 d . . . . .
C5 C 0.7480(4) 0.0047(3) 0.5575(3) 0.0391(9) Uani 1 1 d . . . . .
H5 H 0.798347 -0.057771 0.530350 0.047 Uiso 1 1 calc R U . . .
C6 C 0.7639(4) 0.0100(3) 0.6597(3) 0.0446(10) Uani 1 1 d . . . . .
H6 H 0.823887 -0.051515 0.702594 0.054 Uiso 1 1 calc R U . . .
C7 C 0.6955(4) 0.1019(3) 0.7033(3) 0.0341(8) Uani 1 1 d . . . . .
H7 H 0.710534 0.103944 0.774466 0.041 Uiso 1 1 calc R U . . .
C8 C 0.3036(4) 0.5209(3) 0.7222(3) 0.0322(8) Uani 1 1 d . . . . .
H8 H 0.362755 0.487161 0.785560 0.039 Uiso 1 1 calc R U . . .
C9 C 0.1816(4) 0.6037(3) 0.7108(3) 0.0369(8) Uani 1 1 d . . . . .
H9 H 0.143436 0.636219 0.763503 0.044 Uiso 1 1 calc R U . . .
C10 C 0.1236(4) 0.6315(3) 0.6065(3) 0.0324(8) Uani 1 1 d . . . . .
C11 C 0.2215(3) 0.5596(3) 0.5634(2) 0.0243(7) Uani 1 1 d . . . . .
C12 C 0.0079(4) 0.7019(3) 0.5386(3) 0.0408(9) Uani 1 1 d . . . . .
H12 H -0.063567 0.751144 0.562000 0.049 Uiso 1 1 calc R U . . .
C13 C -0.0010(4) 0.6988(3) 0.4364(3) 0.0403(9) Uani 1 1 d . . . . .
H13 H -0.079372 0.747211 0.390238 0.048 Uiso 1 1 calc R U . . .
C14 C 0.1004(4) 0.6278(3) 0.3992(3) 0.0311(7) Uani 1 1 d . . . . .
H14 H 0.092190 0.627963 0.328822 0.037 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.997(2) . ?
Cu1 O2 2.011(2) . ?
Cu1 N1 1.918(2) . ?
Cu1 N3 1.933(2) . ?
O1 N2 1.347(3) . ?
O2 N4 1.357(3) . ?
N1 C1 1.367(4) . ?
N1 C4 1.349(4) . ?
N2 C4 1.333(4) . ?
N2 C7 1.347(4) . ?
N3 C8 1.378(4) . ?
N3 C11 1.336(4) . ?
N4 C11 1.337(4) . ?
N4 C14 1.344(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.386(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.411(5) . ?
C3 C4 1.402(4) . ?
C3 C5 1.398(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.373(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.396(5) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.376(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.410(5) . ?
C10 C11 1.414(4) . ?
C10 C12 1.395(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.384(5) . ?
C14 H14 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O2 176.54(8) . . ?
N1 Cu1 O1 85.13(10) . . ?
N1 Cu1 O2 94.37(10) . . ?
N1 Cu1 N3 170.05(10) . . ?
N3 Cu1 O1 95.57(10) . . ?
N3 Cu1 O2 84.32(9) . . ?
N2 O1 Cu1 108.08(17) . . ?
N4 O2 Cu1 107.84(16) . . ?
C1 N1 Cu1 147.6(2) . . ?
C4 N1 Cu1 108.2(2) . . ?
C4 N1 C1 103.8(2) . . ?
C4 N2 O1 116.9(2) . . ?
C4 N2 C7 119.5(3) . . ?
C7 N2 O1 123.6(3) . . ?
C8 N3 Cu1 147.3(2) . . ?
C11 N3 Cu1 108.3(2) . . ?
C11 N3 C8 103.7(3) . . ?
C11 N4 O2 116.4(2) . . ?
C11 N4 C14 120.1(3) . . ?
C14 N4 O2 123.6(3) . . ?
N1 C1 H1 123.9 . . ?
N1 C1 C2 112.2(3) . . ?
C2 C1 H1 123.9 . . ?
C1 C2 H2 126.8 . . ?
C1 C2 C3 106.4(3) . . ?
C3 C2 H2 126.8 . . ?
C4 C3 C2 103.8(3) . . ?
C5 C3 C2 140.0(3) . . ?
C5 C3 C4 116.2(3) . . ?
N1 C4 C3 113.7(3) . . ?
N2 C4 N1 121.5(3) . . ?
N2 C4 C3 124.7(3) . . ?
C3 C5 H5 120.8 . . ?
C6 C5 C3 118.4(3) . . ?
C6 C5 H5 120.8 . . ?
C5 C6 H6 118.6 . . ?
C5 C6 C7 122.7(3) . . ?
C7 C6 H6 118.6 . . ?
N2 C7 C6 118.5(3) . . ?
N2 C7 H7 120.7 . . ?
C6 C7 H7 120.7 . . ?
N3 C8 H8 124.0 . . ?
C9 C8 N3 111.9(3) . . ?
C9 C8 H8 124.0 . . ?
C8 C9 H9 126.4 . . ?
C8 C9 C10 107.2(3) . . ?
C10 C9 H9 126.4 . . ?
C9 C10 C11 102.9(3) . . ?
C12 C10 C9 141.1(3) . . ?
C12 C10 C11 115.9(3) . . ?
N3 C11 N4 121.9(3) . . ?
N3 C11 C10 114.2(3) . . ?
N4 C11 C10 123.9(3) . . ?
C10 C12 H12 120.6 . . ?
C13 C12 C10 118.9(3) . . ?
C13 C12 H12 120.6 . . ?
C12 C13 H13 118.8 . . ?
C14 C13 C12 122.3(3) . . ?
C14 C13 H13 118.8 . . ?
N4 C14 C13 118.9(3) . . ?
N4 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 N2 C4 -2.2(3) . . . . ?
Cu1 O1 N2 C7 176.9(2) . . . . ?
Cu1 O2 N4 C11 7.9(3) . . . . ?
Cu1 O2 N4 C14 -172.8(2) . . . . ?
Cu1 N1 C1 C2 171.0(3) . . . . ?
Cu1 N1 C4 N2 2.9(3) . . . . ?
Cu1 N1 C4 C3 -175.4(2) . . . . ?
Cu1 N3 C8 C9 -168.2(3) . . . . ?
Cu1 N3 C11 N4 -7.8(3) . . . . ?
Cu1 N3 C11 C10 173.1(2) . . . . ?
O1 N2 C4 N1 -0.5(4) . . . . ?
O1 N2 C4 C3 177.6(3) . . . . ?
O1 N2 C7 C6 -178.8(3) . . . . ?
O2 N4 C11 N3 -0.3(4) . . . . ?
O2 N4 C11 C10 178.7(2) . . . . ?
O2 N4 C14 C13 -179.7(3) . . . . ?
N1 C1 C2 C3 0.1(4) . . . . ?
N3 C8 C9 C10 0.2(4) . . . . ?
C1 N1 C4 N2 177.7(3) . . . . ?
C1 N1 C4 C3 -0.5(3) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C1 C2 C3 C5 -178.6(4) . . . . ?
C2 C3 C4 N1 0.6(3) . . . . ?
C2 C3 C4 N2 -177.6(3) . . . . ?
C2 C3 C5 C6 178.5(4) . . . . ?
C3 C5 C6 C7 -1.7(5) . . . . ?
C4 N1 C1 C2 0.3(3) . . . . ?
C4 N2 C7 C6 0.3(4) . . . . ?
C4 C3 C5 C6 0.5(4) . . . . ?
C5 C3 C4 N1 179.3(3) . . . . ?
C5 C3 C4 N2 1.1(4) . . . . ?
C5 C6 C7 N2 1.3(5) . . . . ?
C7 N2 C4 N1 -179.6(3) . . . . ?
C7 N2 C4 C3 -1.5(4) . . . . ?
C8 N3 C11 N4 179.0(3) . . . . ?
C8 N3 C11 C10 -0.2(3) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C8 C9 C10 C12 179.2(4) . . . . ?
C9 C10 C11 N3 0.3(3) . . . . ?
C9 C10 C11 N4 -178.8(3) . . . . ?
C9 C10 C12 C13 179.2(4) . . . . ?
C10 C12 C13 C14 0.4(5) . . . . ?
C11 N3 C8 C9 0.0(3) . . . . ?
C11 N4 C14 C13 -0.4(4) . . . . ?
C11 C10 C12 C13 -1.3(4) . . . . ?
C12 C10 C11 N3 -179.4(3) . . . . ?
C12 C10 C11 N4 1.5(4) . . . . ?
C12 C13 C14 N4 0.5(5) . . . . ?
C14 N4 C11 N3 -179.7(3) . . . . ?
C14 N4 C11 C10 -0.7(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 2288064'
loop_
_audit_author_name
_audit_author_address
'Chris Hawes'
;Keele University
United Kingdom
;
_audit_update_record             
;
2023-08-10 deposited with the CCDC.	2023-11-01 downloaded from the CCDC.
;
_audit_creation_date             2023-08-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C42 H36 Cl6 Eu2 N12 O6'
_chemical_formula_sum            'C42 H36 Cl6 Eu2 N12 O6'
_chemical_formula_weight         1321.45
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4097(3)
_cell_length_b                   10.7232(4)
_cell_length_c                   13.8568(5)
_cell_angle_alpha                79.1160(10)
_cell_angle_beta                 80.1310(10)
_cell_angle_gamma                79.9150(10)
_cell_volume                     1195.72(8)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      28.223
_cell_measurement_theta_min      2.486
_shelx_estimated_absorpt_T_max   0.796
_shelx_estimated_absorpt_T_min   0.646
_exptl_absorpt_coefficient_mu    2.994
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0592 before and 0.0525 after correction.
The Ratio of minimum to maximum transmission is 0.9266.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.835
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            26086
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.335
_diffrn_reflns_theta_min         2.661
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Quest ECO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5114
_reflns_number_total             5964
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         2.124
_refine_diff_density_min         -1.364
_refine_diff_density_rms         0.118
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     394
_refine_ls_number_reflns         5964
_refine_ls_number_restraints     174
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0331
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0113P)²+3.0433P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0603
_refine_ls_wR_factor_ref         0.0644
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 N4-H4 = N2-H2
 0.88 with sigma of 0.02
 N7-C22 \\sim N7-C26 \\sim N5-C19 \\sim N5-C15 \\sim N6-C19 \\sim N8-C26
 with sigma of 0.02
 N8-C28 \\sim N6-C21
 with sigma of 0.02
 C19-C18 \\sim C25-C26
 with sigma of 0.02
 C27-C25 \\sim C20-C18
 with sigma of 0.02
 C16-C15 \\sim C17-C16 \\sim C17-C18 \\sim C23-C22 \\sim C23-C24 \\sim C25-C24
 with sigma of 0.02
 C20-C21 \\sim C27-C28
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 N5, N6, C15, C16, C17, C18, C19, C20, C21, N7, N8, C22, C23, C24, C25, C26,
 C27, C28
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Fixed Sof: N5(0.5) N6(0.5) H6A(0.5) C15(0.5) H15(0.5) C16(0.5) H16(0.5)
 C17(0.5) H17(0.5) C18(0.5) C19(0.5) C20(0.5) H20(0.5) C21(0.5) H21(0.5)
 N7(0.5) N8(0.5) H8A(0.5) C22(0.5) H22(0.5) C23(0.5) H23(0.5) C24(0.5) H24(0.5)
 C25(0.5) C26(0.5) C27(0.5) H27(0.5) C28(0.5) H28(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13),
 C14(H14), N6(H6A), C15(H15), C16(H16), C17(H17), C20(H20), C21(H21), N8(H8A),
 C22(H22), C23(H23), C24(H24), C27(H27), C28(H28)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Eu1 Eu 0.54434(2) 0.58288(2) 0.34687(2) 0.02347(6) Uani 1 1 d . . . . .
Cl1 Cl 0.79770(16) 0.65898(15) 0.40188(8) 0.0608(4) Uani 1 1 d . . . . .
Cl2 Cl 0.29349(13) 0.48825(11) 0.30261(8) 0.0434(3) Uani 1 1 d . . . . .
Cl3 Cl 0.63905(11) 0.68855(9) 0.15667(6) 0.02897(19) Uani 1 1 d . . . . .
O1 O 0.7046(4) 0.4160(3) 0.28308(17) 0.0362(7) Uani 1 1 d . . . . .
O2 O 0.3833(3) 0.7836(2) 0.33682(18) 0.0337(6) Uani 1 1 d . . . . .
O3 O 0.4096(3) 0.6013(2) 0.51442(18) 0.0363(7) Uani 1 1 d . . . . .
N1 N 0.8042(4) 0.3940(3) 0.1986(2) 0.0343(8) Uani 1 1 d . . . . .
N2 N 0.5756(4) 0.3717(3) 0.1259(2) 0.0283(7) Uani 1 1 d D . . . .
H2 H 0.497(4) 0.389(4) 0.175(2) 0.034 Uiso 1 1 d D U . . .
N3 N 0.3522(4) 0.8724(3) 0.2579(2) 0.0301(7) Uani 1 1 d . . . . .
N4 N 0.0929(4) 0.8082(3) 0.2563(2) 0.0331(7) Uani 1 1 d D . . . .
H4 H 0.097(5) 0.736(3) 0.296(3) 0.040 Uiso 1 1 d D U . . .
C1 C 0.9663(4) 0.3938(4) 0.1875(3) 0.0316(8) Uani 1 1 d . . . . .
H1 H 1.013623 0.413465 0.239247 0.038 Uiso 1 1 calc R U . . .
C2 C 1.0649(5) 0.3651(4) 0.1013(3) 0.0453(11) Uani 1 1 d . . . . .
H2A H 1.179457 0.363637 0.094914 0.054 Uiso 1 1 calc R U . . .
C3 C 0.9972(6) 0.3387(4) 0.0243(3) 0.0475(12) Uani 1 1 d . . . . .
H3 H 1.064317 0.318943 -0.034949 0.057 Uiso 1 1 calc R U . . .
C4 C 0.8299(5) 0.3416(4) 0.0356(3) 0.0362(10) Uani 1 1 d . . . . .
C5 C 0.7368(5) 0.3705(4) 0.1264(3) 0.0330(9) Uani 1 1 d . . . . .
C6 C 0.7121(6) 0.3279(4) -0.0217(3) 0.0401(10) Uani 1 1 d . . . . .
H6 H 0.733545 0.308557 -0.087194 0.048 Uiso 1 1 calc R U . . .
C7 C 0.5646(6) 0.3471(4) 0.0328(3) 0.0373(10) Uani 1 1 d . . . . .
H7 H 0.464997 0.344270 0.010279 0.045 Uiso 1 1 calc R U . . .
C8 C 0.4590(6) 0.9532(4) 0.2125(3) 0.0405(10) Uani 1 1 d . . . . .
H8 H 0.559152 0.947560 0.237104 0.049 Uiso 1 1 calc R U . . .
C9 C 0.4248(7) 1.0438(4) 0.1308(4) 0.0525(13) Uani 1 1 d . . . . .
H9 H 0.503196 1.097837 0.099060 0.063 Uiso 1 1 calc R U . . .
C10 C 0.2795(7) 1.0573(4) 0.0945(3) 0.0499(13) Uani 1 1 d . . . . .
H10 H 0.255818 1.120801 0.038954 0.060 Uiso 1 1 calc R U . . .
C11 C 0.1682(6) 0.9757(4) 0.1413(3) 0.0385(10) Uani 1 1 d . . . . .
C12 C 0.2112(5) 0.8816(3) 0.2224(3) 0.0299(8) Uani 1 1 d . . . . .
C13 C 0.0110(6) 0.9544(5) 0.1297(3) 0.0492(12) Uani 1 1 d . . . . .
H13 H -0.054622 1.003286 0.082386 0.059 Uiso 1 1 calc R U . . .
C14 C -0.0292(6) 0.8523(5) 0.1977(3) 0.0441(11) Uani 1 1 d . . . . .
H14 H -0.126780 0.816407 0.204244 0.053 Uiso 1 1 calc R U . . .
N5 N 0.3641(7) 0.7266(6) 0.5430(4) 0.0199(10) Uani 0.5 1 d D . P A 1
N6 N 0.0877(10) 0.6914(12) 0.5507(10) 0.027(2) Uani 0.5 1 d D . P A 1
H6A H 0.104854 0.616517 0.530521 0.033 Uiso 0.5 1 calc R U P A 1
C15 C 0.4595(18) 0.8087(18) 0.556(2) 0.028(2) Uani 0.5 1 d D . P A 1
H15 H 0.574663 0.788121 0.541229 0.033 Uiso 0.5 1 calc R U P A 1
C16 C 0.3947(12) 0.9213(9) 0.5905(8) 0.0352(18) Uani 0.5 1 d D . P A 1
H16 H 0.465152 0.975170 0.602481 0.042 Uiso 0.5 1 calc R U P A 1
C17 C 0.2301(11) 0.9565(10) 0.6077(7) 0.0352(18) Uani 0.5 1 d D . P A 1
H17 H 0.185686 1.035839 0.629560 0.042 Uiso 0.5 1 calc R U P A 1
C18 C 0.1288(12) 0.8766(7) 0.5931(6) 0.0266(15) Uani 0.5 1 d D . P A 1
C19 C 0.2038(8) 0.7601(7) 0.5588(4) 0.0209(11) Uani 0.5 1 d D . P A 1
C20 C -0.0416(11) 0.8717(8) 0.6051(6) 0.0338(17) Uani 0.5 1 d D . P A 1
H20 H -0.126017 0.935825 0.627002 0.041 Uiso 0.5 1 calc R U P A 1
C21 C -0.0632(11) 0.7598(9) 0.5800(8) 0.036(2) Uani 0.5 1 d D . P A 1
H21 H -0.165590 0.732774 0.582138 0.043 Uiso 0.5 1 calc R U P A 1
N7 N 0.2748(8) 0.6913(6) 0.5313(4) 0.0269(11) Uani 0.5 1 d D . P A 2
N8 N 0.4707(15) 0.7987(16) 0.5719(19) 0.037(4) Uani 0.5 1 d D . P A 2
H8A H 0.560125 0.744236 0.559725 0.044 Uiso 0.5 1 calc R U P A 2
C22 C 0.1145(13) 0.6908(15) 0.5290(13) 0.031(2) Uani 0.5 1 d D . P A 2
H22 H 0.083377 0.622403 0.505274 0.037 Uiso 0.5 1 calc R U P A 2
C23 C -0.0045(12) 0.7860(9) 0.5599(8) 0.0362(19) Uani 0.5 1 d D . P A 2
H23 H -0.116273 0.782241 0.558944 0.043 Uiso 0.5 1 calc R U P A 2
C24 C 0.0398(14) 0.8864(8) 0.5922(7) 0.0358(18) Uani 0.5 1 d D . P A 2
H24 H -0.041267 0.952526 0.614237 0.043 Uiso 0.5 1 calc R U P A 2
C25 C 0.2000(12) 0.8911(9) 0.5926(6) 0.0310(16) Uani 0.5 1 d D . P A 2
C26 C 0.3178(10) 0.7878(8) 0.5609(5) 0.0290(13) Uani 0.5 1 d D . P A 2
C27 C 0.2982(13) 0.9697(10) 0.6200(8) 0.043(2) Uani 0.5 1 d D . P A 2
H27 H 0.259508 1.048541 0.643962 0.052 Uiso 0.5 1 calc R U P A 2
C28 C 0.4571(13) 0.9138(11) 0.6065(11) 0.052(3) Uani 0.5 1 d D . P A 2
H28 H 0.546324 0.948806 0.619075 0.063 Uiso 0.5 1 calc R U P A 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
Eu1 Eu1 4.2727(4) 2_666 ?
Eu1 Cl1 2.6810(12) . ?
Eu1 Cl2 2.6989(11) . ?
Eu1 Cl3 2.7080(8) . ?
Eu1 O1 2.268(2) . ?
Eu1 O2 2.327(2) . ?
Eu1 O3 2.430(2) . ?
Eu1 O3 2.509(2) 2_666 ?
O1 N1 1.352(4) . ?
O2 N3 1.338(4) . ?
O3 N5 1.441(7) . ?
O3 N7 1.372(7) . ?
N1 C1 1.345(5) . ?
N1 C5 1.313(5) . ?
N2 H2 0.885(18) . ?
N2 C5 1.354(5) . ?
N2 C7 1.385(5) . ?
N3 C8 1.352(5) . ?
N3 C12 1.341(5) . ?
N4 H4 0.860(19) . ?
N4 C12 1.343(5) . ?
N4 C14 1.381(5) . ?
C1 H1 0.9500 . ?
C1 C2 1.385(5) . ?
C2 H2A 0.9500 . ?
C2 C3 1.386(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(6) . ?
C4 C5 1.421(5) . ?
C4 C6 1.413(6) . ?
C6 H6 0.9500 . ?
C6 C7 1.340(6) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.381(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.374(7) . ?
C10 H10 0.9500 . ?
C10 C11 1.389(6) . ?
C11 C12 1.412(5) . ?
C11 C13 1.421(7) . ?
C13 H13 0.9500 . ?
C13 C14 1.353(7) . ?
C14 H14 0.9500 . ?
N5 C15 1.346(11) . ?
N5 C19 1.324(8) . ?
N6 H6A 0.8800 . ?
N6 C19 1.352(9) . ?
N6 C21 1.386(11) . ?
C15 H15 0.9500 . ?
C15 C16 1.371(13) . ?
C16 H16 0.9500 . ?
C16 C17 1.361(10) . ?
C17 H17 0.9500 . ?
C17 C18 1.371(10) . ?
C18 C19 1.424(9) . ?
C18 C20 1.423(10) . ?
C20 H20 0.9500 . ?
C20 C21 1.360(11) . ?
C21 H21 0.9500 . ?
N7 C22 1.355(11) . ?
N7 C26 1.309(9) . ?
N8 H8A 0.8800 . ?
N8 C26 1.348(11) . ?
N8 C28 1.386(13) . ?
C22 H22 0.9500 . ?
C22 C23 1.374(11) . ?
C23 H23 0.9500 . ?
C23 C24 1.370(10) . ?
C24 H24 0.9500 . ?
C24 C25 1.358(10) . ?
C25 C26 1.432(10) . ?
C25 C27 1.418(12) . ?
C27 H27 0.9500 . ?
C27 C28 1.363(12) . ?
C28 H28 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Eu1 Eu1 83.60(3) . 2_666 ?
Cl1 Eu1 Cl2 175.23(4) . . ?
Cl1 Eu1 Cl3 89.62(3) . . ?
Cl2 Eu1 Eu1 92.49(2) . 2_666 ?
Cl2 Eu1 Cl3 94.17(3) . . ?
Cl3 Eu1 Eu1 172.83(2) . 2_666 ?
O1 Eu1 Eu1 100.74(6) . 2_666 ?
O1 Eu1 Cl1 92.62(8) . . ?
O1 Eu1 Cl2 85.40(8) . . ?
O1 Eu1 Cl3 77.16(7) . . ?
O1 Eu1 O2 154.40(9) . . ?
O1 Eu1 O3 71.20(8) . 2_666 ?
O1 Eu1 O3 131.33(9) . . ?
O2 Eu1 Eu1 104.33(6) . 2_666 ?
O2 Eu1 Cl1 95.20(8) . . ?
O2 Eu1 Cl2 88.41(8) . . ?
O2 Eu1 Cl3 78.56(6) . . ?
O2 Eu1 O3 73.69(8) . . ?
O2 Eu1 O3 133.90(8) . 2_666 ?
O3 Eu1 Eu1 29.59(5) 2_666 2_666 ?
O3 Eu1 Eu1 30.66(6) . 2_666 ?
O3 Eu1 Cl1 85.47(8) . . ?
O3 Eu1 Cl1 83.50(8) 2_666 . ?
O3 Eu1 Cl2 92.57(8) . . ?
O3 Eu1 Cl2 91.74(8) 2_666 . ?
O3 Eu1 Cl3 147.20(6) 2_666 . ?
O3 Eu1 Cl3 151.22(6) . . ?
O3 Eu1 O3 60.25(10) . 2_666 ?
N1 O1 Eu1 138.7(2) . . ?
N3 O2 Eu1 130.5(2) . . ?
Eu1 O3 Eu1 119.75(10) . 2_666 ?
N5 O3 Eu1 115.9(3) . 2_666 ?
N5 O3 Eu1 119.3(3) . . ?
N7 O3 Eu1 121.1(3) . . ?
C1 N1 O1 122.5(3) . . ?
C5 N1 O1 117.2(3) . . ?
C5 N1 C1 120.2(3) . . ?
C5 N2 H2 126(3) . . ?
C5 N2 C7 105.2(3) . . ?
C7 N2 H2 129(3) . . ?
O2 N3 C8 121.9(4) . . ?
O2 N3 C12 119.2(3) . . ?
C12 N3 C8 118.9(3) . . ?
C12 N4 H4 129(3) . . ?
C12 N4 C14 107.1(4) . . ?
C14 N4 H4 123(3) . . ?
N1 C1 H1 119.7 . . ?
N1 C1 C2 120.7(4) . . ?
C2 C1 H1 119.7 . . ?
C1 C2 H2A 119.8 . . ?
C1 C2 C3 120.3(4) . . ?
C3 C2 H2A 119.8 . . ?
C2 C3 H3 120.7 . . ?
C4 C3 C2 118.6(4) . . ?
C4 C3 H3 120.7 . . ?
C3 C4 C5 117.9(4) . . ?
C3 C4 C6 138.0(4) . . ?
C6 C4 C5 104.1(4) . . ?
N1 C5 N2 126.7(4) . . ?
N1 C5 C4 122.2(4) . . ?
N2 C5 C4 111.1(4) . . ?
C4 C6 H6 126.0 . . ?
C7 C6 C4 108.0(4) . . ?
C7 C6 H6 126.0 . . ?
N2 C7 H7 124.2 . . ?
C6 C7 N2 111.6(4) . . ?
C6 C7 H7 124.2 . . ?
N3 C8 H8 119.5 . . ?
N3 C8 C9 121.0(4) . . ?
C9 C8 H8 119.5 . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.3(4) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 120.9 . . ?
C9 C10 C11 118.1(4) . . ?
C11 C10 H10 120.9 . . ?
C10 C11 C12 118.5(4) . . ?
C10 C11 C13 137.3(4) . . ?
C12 C11 C13 104.2(4) . . ?
N3 C12 N4 127.1(3) . . ?
N3 C12 C11 122.2(4) . . ?
N4 C12 C11 110.7(4) . . ?
C11 C13 H13 125.9 . . ?
C14 C13 C11 108.2(4) . . ?
C14 C13 H13 125.9 . . ?
N4 C14 H14 125.1 . . ?
C13 C14 N4 109.8(4) . . ?
C13 C14 H14 125.1 . . ?
C15 N5 O3 129.4(8) . . ?
C19 N5 O3 112.3(6) . . ?
C19 N5 C15 118.3(9) . . ?
C19 N6 H6A 126.1 . . ?
C19 N6 C21 107.9(8) . . ?
C21 N6 H6A 126.1 . . ?
N5 C15 H15 119.2 . . ?
N5 C15 C16 121.6(13) . . ?
C16 C15 H15 119.2 . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.5(9) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 120.3 . . ?
C16 C17 C18 119.5(9) . . ?
C18 C17 H17 120.3 . . ?
C17 C18 C19 117.2(8) . . ?
C17 C18 C20 138.2(8) . . ?
C20 C18 C19 104.6(7) . . ?
N5 C19 N6 127.5(8) . . ?
N5 C19 C18 122.7(7) . . ?
N6 C19 C18 109.7(7) . . ?
C18 C20 H20 125.8 . . ?
C21 C20 C18 108.5(7) . . ?
C21 C20 H20 125.8 . . ?
N6 C21 H21 125.3 . . ?
C20 C21 N6 109.4(9) . . ?
C20 C21 H21 125.3 . . ?
C22 N7 O3 131.7(7) . . ?
C26 N7 O3 109.4(7) . . ?
C26 N7 C22 118.7(9) . . ?
C26 N8 H8A 127.3 . . ?
C26 N8 C28 105.3(11) . . ?
C28 N8 H8A 127.3 . . ?
N7 C22 H22 118.9 . . ?
N7 C22 C23 122.2(11) . . ?
C23 C22 H22 118.9 . . ?
C22 C23 H23 120.4 . . ?
C24 C23 C22 119.2(10) . . ?
C24 C23 H23 120.4 . . ?
C23 C24 H24 120.1 . . ?
C25 C24 C23 119.8(9) . . ?
C25 C24 H24 120.1 . . ?
C24 C25 C26 118.2(9) . . ?
C24 C25 C27 139.1(8) . . ?
C27 C25 C26 102.7(7) . . ?
N7 C26 N8 125.6(10) . . ?
N7 C26 C25 121.9(8) . . ?
N8 C26 C25 112.4(9) . . ?
C25 C27 H27 125.6 . . ?
C28 C27 C25 108.8(9) . . ?
C28 C27 H27 125.6 . . ?
N8 C28 H28 124.7 . . ?
C27 C28 N8 110.7(10) . . ?
C27 C28 H28 124.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 Cl2 0.885(18) 2.50(2) 3.364(3) 166(4) . yes
N4 H4 Cl2 0.860(19) 2.87(3) 3.541(4) 136(4) . yes
N6 H6A Cl1 0.88 2.94 3.673(13) 141.9 2_666 yes
N8 H8A Cl1 0.88 2.87 3.609(18) 142.8 . yes
N8 H8A Cl2 0.88 3.05 3.67(2) 128.9 2_666 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Eu1 O1 N1 C1 94.3(4) . . . . ?
Eu1 O1 N1 C5 -86.7(5) . . . . ?
Eu1 O2 N3 C8 -79.6(4) . . . . ?
Eu1 O2 N3 C12 100.2(3) . . . . ?
Eu1 O3 N5 C15 -68.8(18) . . . . ?
Eu1 O3 N5 C15 85.9(18) 2_666 . . . ?
Eu1 O3 N5 C19 112.2(5) . . . . ?
Eu1 O3 N5 C19 -93.2(5) 2_666 . . . ?
Eu1 O3 N7 C22 -78.2(12) 2_666 . . . ?
Eu1 O3 N7 C22 83.0(13) . . . . ?
Eu1 O3 N7 C26 -102.2(5) . . . . ?
Eu1 O3 N7 C26 96.6(5) 2_666 . . . ?
O1 N1 C1 C2 177.1(4) . . . . ?
O1 N1 C5 N2 3.3(6) . . . . ?
O1 N1 C5 C4 -177.7(3) . . . . ?
O2 N3 C8 C9 179.7(4) . . . . ?
O2 N3 C12 N4 -1.4(5) . . . . ?
O2 N3 C12 C11 177.9(3) . . . . ?
O3 N5 C15 C16 -175.3(14) . . . . ?
O3 N5 C19 N6 -0.1(11) . . . . ?
O3 N5 C19 C18 176.4(6) . . . . ?
O3 N7 C22 C23 172.1(9) . . . . ?
O3 N7 C26 N8 0.9(16) . . . . ?
O3 N7 C26 C25 -174.3(6) . . . . ?
N1 C1 C2 C3 1.3(7) . . . . ?
N3 C8 C9 C10 1.8(7) . . . . ?
C1 N1 C5 N2 -177.6(4) . . . . ?
C1 N1 C5 C4 1.3(6) . . . . ?
C1 C2 C3 C4 0.0(7) . . . . ?
C2 C3 C4 C5 -0.6(6) . . . . ?
C2 C3 C4 C6 176.2(5) . . . . ?
C3 C4 C5 N1 0.0(6) . . . . ?
C3 C4 C5 N2 179.1(4) . . . . ?
C3 C4 C6 C7 -177.3(5) . . . . ?
C4 C6 C7 N2 -0.9(5) . . . . ?
C5 N1 C1 C2 -1.9(6) . . . . ?
C5 N2 C7 C6 1.6(5) . . . . ?
C5 C4 C6 C7 -0.2(5) . . . . ?
C6 C4 C5 N1 -177.8(4) . . . . ?
C6 C4 C5 N2 1.2(4) . . . . ?
C7 N2 C5 N1 177.3(4) . . . . ?
C7 N2 C5 C4 -1.7(4) . . . . ?
C8 N3 C12 N4 178.5(4) . . . . ?
C8 N3 C12 C11 -2.2(5) . . . . ?
C8 C9 C10 C11 -1.0(7) . . . . ?
C9 C10 C11 C12 -1.2(6) . . . . ?
C9 C10 C11 C13 -179.1(5) . . . . ?
C10 C11 C12 N3 2.9(6) . . . . ?
C10 C11 C12 N4 -177.7(3) . . . . ?
C10 C11 C13 C14 176.3(5) . . . . ?
C11 C13 C14 N4 2.2(5) . . . . ?
C12 N3 C8 C9 -0.1(6) . . . . ?
C12 N4 C14 C13 -1.6(5) . . . . ?
C12 C11 C13 C14 -1.8(5) . . . . ?
C13 C11 C12 N3 -178.5(3) . . . . ?
C13 C11 C12 N4 0.9(4) . . . . ?
C14 N4 C12 N3 179.7(4) . . . . ?
C14 N4 C12 C11 0.4(4) . . . . ?
N5 C15 C16 C17 -3(3) . . . . ?
C15 N5 C19 N6 -179.3(18) . . . . ?
C15 N5 C19 C18 -2.8(18) . . . . ?
C15 C16 C17 C18 2(2) . . . . ?
C16 C17 C18 C19 -1.0(12) . . . . ?
C16 C17 C18 C20 176.7(10) . . . . ?
C17 C18 C19 N5 1.5(11) . . . . ?
C17 C18 C19 N6 178.5(9) . . . . ?
C17 C18 C20 C21 -177.5(11) . . . . ?
C18 C20 C21 N6 -0.7(12) . . . . ?
C19 N5 C15 C16 4(3) . . . . ?
C19 N6 C21 C20 0.7(13) . . . . ?
C19 C18 C20 C21 0.3(9) . . . . ?
C20 C18 C19 N5 -176.9(6) . . . . ?
C20 C18 C19 N6 0.1(10) . . . . ?
C21 N6 C19 N5 176.4(8) . . . . ?
C21 N6 C19 C18 -0.5(13) . . . . ?
N7 C22 C23 C24 1(2) . . . . ?
C22 N7 C26 N8 176.4(17) . . . . ?
C22 N7 C26 C25 1.2(14) . . . . ?
C22 C23 C24 C25 0.5(16) . . . . ?
C23 C24 C25 C26 -1.4(13) . . . . ?
C23 C24 C25 C27 -178.1(11) . . . . ?
C24 C25 C26 N7 0.6(12) . . . . ?
C24 C25 C26 N8 -175.2(14) . . . . ?
C24 C25 C27 C28 175.9(12) . . . . ?
C25 C27 C28 N8 -0.8(17) . . . . ?
C26 N7 C22 C23 -2(2) . . . . ?
C26 N8 C28 C27 2(2) . . . . ?
C26 C25 C27 C28 -1.0(11) . . . . ?
C27 C25 C26 N7 178.3(8) . . . . ?
C27 C25 C26 N8 2.6(15) . . . . ?
C28 N8 C26 N7 -178.6(11) . . . . ?
C28 N8 C26 C25 -3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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 2288062'
loop_
_audit_author_name
_audit_author_address
'Chris Hawes'
;Keele University
United Kingdom
;
_audit_update_record             
;
2023-08-10 deposited with the CCDC.	2023-11-01 downloaded from the CCDC.
;
_audit_creation_date             2023-08-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H18 Eu N9 O12'
_chemical_formula_sum            'C21 H18 Eu N9 O12'
_chemical_formula_weight         740.40
_chemical_melting_point          ?
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'
Eu Eu -0.1578 3.6682 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5699(4)
_cell_length_b                   11.7452(6)
_cell_length_c                   14.2218(7)
_cell_angle_alpha                78.6540(10)
_cell_angle_beta                 77.1540(10)
_cell_angle_gamma                70.8060(10)
_cell_volume                     1306.15(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9950
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      30.511
_cell_measurement_theta_min      2.703
_shelx_estimated_absorpt_T_max   0.663
_shelx_estimated_absorpt_T_min   0.523
_exptl_absorpt_coefficient_mu    2.484
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6391
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0553 before and 0.0358 after correction.
The Ratio of minimum to maximum transmission is 0.8566.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.883
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             732
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            37986
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.543
_diffrn_reflns_theta_min         3.164
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Quest ECO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7700
_reflns_number_total             7957
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.727
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         7957
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0169
_refine_ls_R_factor_gt           0.0159
_refine_ls_restrained_S_all      1.169
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0097P)²+0.8269P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0378
_refine_ls_wR_factor_ref         0.0381
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 N4-H4 = N2-H2 = N6-H6
 0.88 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3), C6(H6A), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13),
 C14(H14), C15(H15), C16(H16), C17(H17), C20(H20), C21(H21)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Eu1 Eu 0.52253(2) 0.30180(2) 0.28729(2) 0.01390(2) Uani 1 1 d . . . . .
O1 O 0.29507(14) 0.26762(9) 0.40078(7) 0.0191(2) Uani 1 1 d . . . . .
O2 O 0.37919(14) 0.49922(9) 0.32371(7) 0.0190(2) Uani 1 1 d . . . . .
O3 O 0.31266(14) 0.36123(9) 0.18966(8) 0.0192(2) Uani 1 1 d . . . . .
O4 O 0.60001(15) 0.30975(10) 0.44650(8) 0.0238(2) Uani 1 1 d . . . . .
O5 O 0.69664(15) 0.13741(10) 0.39113(8) 0.0253(2) Uani 1 1 d . . . . .
O6 O 0.7982(2) 0.16613(15) 0.50887(11) 0.0463(4) Uani 1 1 d . . . . .
O7 O 0.79040(14) 0.34774(10) 0.25339(8) 0.0212(2) Uani 1 1 d . . . . .
O8 O 0.63114(14) 0.43759(10) 0.14610(8) 0.0218(2) Uani 1 1 d . . . . .
O9 O 0.88497(15) 0.45013(12) 0.12111(10) 0.0319(3) Uani 1 1 d . . . . .
O10 O 0.70231(15) 0.17748(10) 0.16131(8) 0.0235(2) Uani 1 1 d . . . . .
O11 O 0.52100(14) 0.09738(10) 0.25581(9) 0.0245(2) Uani 1 1 d . . . . .
O12 O 0.70645(18) -0.00411(11) 0.14696(9) 0.0329(3) Uani 1 1 d . . . . .
N1 N 0.23603(15) 0.25541(11) 0.49645(9) 0.0160(2) Uani 1 1 d . . . . .
N2 N 0.19761(16) 0.46477(11) 0.50853(9) 0.0179(2) Uani 1 1 d D . . . .
H2 H 0.244(2) 0.4884(17) 0.4519(11) 0.022 Uiso 1 1 d D U . . .
N3 N 0.39714(15) 0.60864(10) 0.28280(9) 0.0160(2) Uani 1 1 d . . . . .
N4 N 0.26836(17) 0.61334(12) 0.14779(9) 0.0205(2) Uani 1 1 d D . . . .
H4 H 0.266(3) 0.5409(14) 0.1577(15) 0.025 Uiso 1 1 d D U . . .
N5 N 0.26522(15) 0.30042(11) 0.13583(9) 0.0179(2) Uani 1 1 d . . . . .
N6 N 0.15710(16) 0.18120(12) 0.27673(10) 0.0202(2) Uani 1 1 d D . . . .
H6 H 0.184(2) 0.2073(18) 0.3221(13) 0.024 Uiso 1 1 d D U . . .
N7 N 0.70068(18) 0.20289(13) 0.45130(10) 0.0243(3) Uani 1 1 d . . . . .
N8 N 0.77274(16) 0.41321(11) 0.17174(9) 0.0191(2) Uani 1 1 d . . . . .
N9 N 0.64453(17) 0.08743(11) 0.18682(9) 0.0200(2) Uani 1 1 d . . . . .
C1 C 0.21925(19) 0.14796(13) 0.54461(11) 0.0203(3) Uani 1 1 d . . . . .
H1 H 0.256119 0.078613 0.511365 0.024 Uiso 1 1 calc R U . . .
C2 C 0.1487(2) 0.13814(14) 0.64211(11) 0.0233(3) Uani 1 1 d . . . . .
H2A H 0.138853 0.061505 0.674979 0.028 Uiso 1 1 calc R U . . .
C3 C 0.0920(2) 0.23708(14) 0.69302(11) 0.0224(3) Uani 1 1 d . . . . .
H3 H 0.041696 0.229750 0.759668 0.027 Uiso 1 1 calc R U . . .
C4 C 0.11105(18) 0.34777(13) 0.64354(10) 0.0182(3) Uani 1 1 d . . . . .
C5 C 0.18605(17) 0.35234(12) 0.54461(10) 0.0159(2) Uani 1 1 d . . . . .
C6 C 0.0770(2) 0.46765(14) 0.66615(11) 0.0224(3) Uani 1 1 d . . . . .
H6A H 0.025989 0.495344 0.727325 0.027 Uiso 1 1 calc R U . . .
C7 C 0.13102(19) 0.53457(14) 0.58385(12) 0.0216(3) Uani 1 1 d . . . . .
H7 H 0.124092 0.617914 0.578668 0.026 Uiso 1 1 calc R U . . .
C8 C 0.46839(19) 0.66743(14) 0.32463(11) 0.0212(3) Uani 1 1 d . . . . .
H8 H 0.510809 0.630331 0.383155 0.025 Uiso 1 1 calc R U . . .
C9 C 0.4803(2) 0.78170(14) 0.28297(13) 0.0248(3) Uani 1 1 d . . . . .
H9 H 0.530976 0.822124 0.313496 0.030 Uiso 1 1 calc R U . . .
C10 C 0.4200(2) 0.83832(14) 0.19772(12) 0.0247(3) Uani 1 1 d . . . . .
H10 H 0.428301 0.916924 0.169579 0.030 Uiso 1 1 calc R U . . .
C11 C 0.34720(19) 0.77711(13) 0.15449(11) 0.0209(3) Uani 1 1 d . . . . .
C12 C 0.33921(18) 0.66074(12) 0.19957(10) 0.0170(2) Uani 1 1 d . . . . .
C13 C 0.2754(2) 0.79785(15) 0.06890(12) 0.0280(3) Uani 1 1 d . . . . .
H13 H 0.260650 0.868852 0.022215 0.034 Uiso 1 1 calc R U . . .
C14 C 0.2322(2) 0.69744(15) 0.06659(12) 0.0273(3) Uani 1 1 d . . . . .
H14 H 0.183868 0.686371 0.016341 0.033 Uiso 1 1 calc R U . . .
C15 C 0.2862(2) 0.32564(14) 0.03791(11) 0.0223(3) Uani 1 1 d . . . . .
H15 H 0.337334 0.386611 0.005743 0.027 Uiso 1 1 calc R U . . .
C16 C 0.2338(2) 0.26341(16) -0.01594(12) 0.0261(3) Uani 1 1 d . . . . .
H16 H 0.248535 0.282901 -0.084768 0.031 Uiso 1 1 calc R U . . .
C17 C 0.1604(2) 0.17321(15) 0.02855(12) 0.0246(3) Uani 1 1 d . . . . .
H17 H 0.126805 0.129604 -0.008961 0.029 Uiso 1 1 calc R U . . .
C18 C 0.13712(18) 0.14816(13) 0.12904(12) 0.0207(3) Uani 1 1 d . . . . .
C19 C 0.19018(18) 0.21586(13) 0.18076(11) 0.0181(3) Uani 1 1 d . . . . .
C20 C 0.0707(2) 0.06625(14) 0.20226(13) 0.0241(3) Uani 1 1 d . . . . .
H20 H 0.024694 0.007321 0.191857 0.029 Uiso 1 1 calc R U . . .
C21 C 0.0856(2) 0.08823(14) 0.28958(12) 0.0238(3) Uani 1 1 d . . . . .
H21 H 0.051806 0.045788 0.350793 0.029 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Eu1 O1 2.3295(10) . ?
Eu1 O2 2.3390(10) . ?
Eu1 O3 2.3566(10) . ?
Eu1 O4 2.5238(11) . ?
Eu1 O5 2.4696(11) . ?
Eu1 O7 2.4523(11) . ?
Eu1 O8 2.5154(11) . ?
Eu1 O10 2.4573(11) . ?
Eu1 O11 2.5321(11) . ?
O1 N1 1.3389(15) . ?
O2 N3 1.3452(15) . ?
O3 N5 1.3439(15) . ?
O4 N7 1.2668(17) . ?
O5 N7 1.2706(18) . ?
O6 N7 1.2175(18) . ?
O7 N8 1.2701(16) . ?
O8 N8 1.2707(17) . ?
O9 N8 1.2144(17) . ?
O10 N9 1.2684(17) . ?
O11 N9 1.2645(17) . ?
O12 N9 1.2206(16) . ?
N1 C1 1.3483(18) . ?
N1 C5 1.3432(18) . ?
N2 H2 0.851(14) . ?
N2 C5 1.3467(18) . ?
N2 C7 1.3825(19) . ?
N3 C8 1.3431(19) . ?
N3 C12 1.3411(18) . ?
N4 H4 0.841(15) . ?
N4 C12 1.3428(19) . ?
N4 C14 1.384(2) . ?
N5 C15 1.3493(19) . ?
N5 C19 1.3401(19) . ?
N6 H6 0.869(15) . ?
N6 C19 1.3395(19) . ?
N6 C21 1.383(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.383(2) . ?
C2 H2A 0.9500 . ?
C2 C3 1.383(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.393(2) . ?
C4 C5 1.409(2) . ?
C4 C6 1.427(2) . ?
C6 H6A 0.9500 . ?
C6 C7 1.356(2) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.383(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.384(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.387(2) . ?
C11 C12 1.4075(19) . ?
C11 C13 1.427(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.355(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C15 C16 1.382(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.384(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.384(2) . ?
C18 C19 1.413(2) . ?
C18 C20 1.427(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.358(2) . ?
C21 H21 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Eu1 O2 79.36(4) . . ?
O1 Eu1 O3 78.84(4) . . ?
O1 Eu1 O4 77.39(4) . . ?
O1 Eu1 O5 85.45(4) . . ?
O1 Eu1 O7 148.60(4) . . ?
O1 Eu1 O8 148.04(4) . . ?
O1 Eu1 O10 128.58(4) . . ?
O1 Eu1 O11 77.57(4) . . ?
O2 Eu1 O3 78.85(4) . . ?
O2 Eu1 O4 74.85(4) . . ?
O2 Eu1 O5 125.84(4) . . ?
O2 Eu1 O7 90.55(4) . . ?
O2 Eu1 O8 75.40(4) . . ?
O2 Eu1 O10 145.58(4) . . ?
O2 Eu1 O11 150.44(4) . . ?
O3 Eu1 O4 147.23(4) . . ?
O3 Eu1 O5 147.69(4) . . ?
O3 Eu1 O7 128.59(4) . . ?
O3 Eu1 O8 77.31(4) . . ?
O3 Eu1 O10 86.95(4) . . ?
O3 Eu1 O11 78.76(4) . . ?
O4 Eu1 O11 117.21(4) . . ?
O5 Eu1 O4 51.08(4) . . ?
O5 Eu1 O8 125.40(4) . . ?
O5 Eu1 O11 70.33(4) . . ?
O7 Eu1 O4 71.27(4) . . ?
O7 Eu1 O5 76.51(4) . . ?
O7 Eu1 O8 51.44(3) . . ?
O7 Eu1 O10 74.08(4) . . ?
O7 Eu1 O11 118.59(4) . . ?
O8 Eu1 O4 113.75(4) . . ?
O8 Eu1 O11 117.72(4) . . ?
O10 Eu1 O4 125.64(4) . . ?
O10 Eu1 O5 81.04(4) . . ?
O10 Eu1 O8 70.93(4) . . ?
O10 Eu1 O11 51.13(4) . . ?
N1 O1 Eu1 142.50(9) . . ?
N3 O2 Eu1 132.61(8) . . ?
N5 O3 Eu1 132.67(8) . . ?
N7 O4 Eu1 94.47(8) . . ?
N7 O5 Eu1 96.95(8) . . ?
N8 O7 Eu1 97.53(8) . . ?
N8 O8 Eu1 94.50(8) . . ?
N9 O10 Eu1 97.81(8) . . ?
N9 O11 Eu1 94.33(8) . . ?
O1 N1 C1 120.81(12) . . ?
O1 N1 C5 119.84(11) . . ?
C5 N1 C1 119.29(12) . . ?
C5 N2 H2 127.6(13) . . ?
C5 N2 C7 106.85(12) . . ?
C7 N2 H2 125.4(13) . . ?
C8 N3 O2 121.38(12) . . ?
C12 N3 O2 118.98(12) . . ?
C12 N3 C8 119.62(12) . . ?
C12 N4 H4 125.0(14) . . ?
C12 N4 C14 106.84(13) . . ?
C14 N4 H4 127.1(14) . . ?
O3 N5 C15 121.45(12) . . ?
C19 N5 O3 119.13(12) . . ?
C19 N5 C15 119.38(13) . . ?
C19 N6 H6 126.4(13) . . ?
C19 N6 C21 107.15(13) . . ?
C21 N6 H6 126.2(13) . . ?
O4 N7 O5 116.15(13) . . ?
O6 N7 O4 121.81(15) . . ?
O6 N7 O5 122.02(14) . . ?
O7 N8 O8 116.15(12) . . ?
O9 N8 O7 121.83(13) . . ?
O9 N8 O8 122.02(13) . . ?
O11 N9 O10 116.53(12) . . ?
O12 N9 O10 121.36(14) . . ?
O12 N9 O11 122.11(13) . . ?
N1 C1 H1 119.8 . . ?
N1 C1 C2 120.36(14) . . ?
C2 C1 H1 119.8 . . ?
C1 C2 H2A 119.2 . . ?
C1 C2 C3 121.67(14) . . ?
C3 C2 H2A 119.2 . . ?
C2 C3 H3 121.0 . . ?
C2 C3 C4 117.96(14) . . ?
C4 C3 H3 121.0 . . ?
C3 C4 C5 118.05(13) . . ?
C3 C4 C6 136.92(14) . . ?
C5 C4 C6 105.02(13) . . ?
N1 C5 N2 126.96(13) . . ?
N1 C5 C4 122.63(13) . . ?
N2 C5 C4 110.41(12) . . ?
C4 C6 H6A 126.5 . . ?
C7 C6 C4 107.09(13) . . ?
C7 C6 H6A 126.5 . . ?
N2 C7 H7 124.7 . . ?
C6 C7 N2 110.64(13) . . ?
C6 C7 H7 124.7 . . ?
N3 C8 H8 119.8 . . ?
N3 C8 C9 120.37(14) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 119.3 . . ?
C8 C9 C10 121.33(15) . . ?
C10 C9 H9 119.3 . . ?
C9 C10 H10 120.9 . . ?
C9 C10 C11 118.15(14) . . ?
C11 C10 H10 120.9 . . ?
C10 C11 C12 118.21(14) . . ?
C10 C11 C13 137.02(15) . . ?
C12 C11 C13 104.74(14) . . ?
N3 C12 N4 126.98(13) . . ?
N3 C12 C11 122.32(13) . . ?
N4 C12 C11 110.71(13) . . ?
C11 C13 H13 126.4 . . ?
C14 C13 C11 107.30(14) . . ?
C14 C13 H13 126.4 . . ?
N4 C14 H14 124.8 . . ?
C13 C14 N4 110.39(14) . . ?
C13 C14 H14 124.8 . . ?
N5 C15 H15 119.8 . . ?
N5 C15 C16 120.49(15) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 119.4 . . ?
C15 C16 C17 121.24(15) . . ?
C17 C16 H16 119.4 . . ?
C16 C17 H17 120.8 . . ?
C18 C17 C16 118.33(15) . . ?
C18 C17 H17 120.8 . . ?
C17 C18 C19 118.17(14) . . ?
C17 C18 C20 137.04(15) . . ?
C19 C18 C20 104.78(14) . . ?
N5 C19 C18 122.35(14) . . ?
N6 C19 N5 127.15(14) . . ?
N6 C19 C18 110.49(13) . . ?
C18 C20 H20 126.4 . . ?
C21 C20 C18 107.23(14) . . ?
C21 C20 H20 126.4 . . ?
N6 C21 H21 124.8 . . ?
C20 C21 N6 110.33(14) . . ?
C20 C21 H21 124.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 O2 0.851(14) 1.938(15) 2.7697(16) 165.6(19) . yes
N4 H4 O3 0.841(15) 1.992(15) 2.8168(16) 167(2) . yes
N6 H6 O1 0.869(15) 1.971(15) 2.8217(17) 165.8(19) . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Eu1 O1 N1 C1 -112.95(15) . . . . ?
Eu1 O1 N1 C5 69.89(18) . . . . ?
Eu1 O2 N3 C8 -104.31(14) . . . . ?
Eu1 O2 N3 C12 77.11(16) . . . . ?
Eu1 O3 N5 C15 -113.26(14) . . . . ?
Eu1 O3 N5 C19 69.08(16) . . . . ?
Eu1 O4 N7 O5 -11.35(14) . . . . ?
Eu1 O4 N7 O6 167.10(15) . . . . ?
Eu1 O5 N7 O4 11.65(14) . . . . ?
Eu1 O5 N7 O6 -166.79(15) . . . . ?
Eu1 O7 N8 O8 6.27(13) . . . . ?
Eu1 O7 N8 O9 -173.61(12) . . . . ?
Eu1 O8 N8 O7 -6.08(12) . . . . ?
Eu1 O8 N8 O9 173.80(13) . . . . ?
Eu1 O10 N9 O11 4.45(13) . . . . ?
Eu1 O10 N9 O12 -175.02(12) . . . . ?
Eu1 O11 N9 O10 -4.29(13) . . . . ?
Eu1 O11 N9 O12 175.18(13) . . . . ?
O1 N1 C1 C2 -176.05(14) . . . . ?
O1 N1 C5 N2 -4.6(2) . . . . ?
O1 N1 C5 C4 175.07(13) . . . . ?
O2 N3 C8 C9 -177.78(13) . . . . ?
O2 N3 C12 N4 -2.9(2) . . . . ?
O2 N3 C12 C11 177.37(13) . . . . ?
O3 N5 C15 C16 -178.87(14) . . . . ?
O3 N5 C19 N6 -1.1(2) . . . . ?
O3 N5 C19 C18 -179.89(12) . . . . ?
N1 C1 C2 C3 0.6(2) . . . . ?
N3 C8 C9 C10 -0.1(2) . . . . ?
N5 C15 C16 C17 -0.6(2) . . . . ?
C1 N1 C5 N2 178.19(14) . . . . ?
C1 N1 C5 C4 -2.1(2) . . . . ?
C1 C2 C3 C4 -1.3(2) . . . . ?
C2 C3 C4 C5 0.3(2) . . . . ?
C2 C3 C4 C6 -177.96(17) . . . . ?
C3 C4 C5 N1 1.4(2) . . . . ?
C3 C4 C5 N2 -178.86(13) . . . . ?
C3 C4 C6 C7 178.23(18) . . . . ?
C4 C6 C7 N2 0.40(18) . . . . ?
C5 N1 C1 C2 1.1(2) . . . . ?
C5 N2 C7 C6 -0.46(17) . . . . ?
C5 C4 C6 C7 -0.19(17) . . . . ?
C6 C4 C5 N1 -179.82(13) . . . . ?
C6 C4 C5 N2 -0.09(17) . . . . ?
C7 N2 C5 N1 -179.95(14) . . . . ?
C7 N2 C5 C4 0.33(16) . . . . ?
C8 N3 C12 N4 178.50(14) . . . . ?
C8 N3 C12 C11 -1.2(2) . . . . ?
C8 C9 C10 C11 -0.2(2) . . . . ?
C9 C10 C11 C12 -0.2(2) . . . . ?
C9 C10 C11 C13 -178.01(18) . . . . ?
C10 C11 C12 N3 0.9(2) . . . . ?
C10 C11 C12 N4 -178.83(14) . . . . ?
C10 C11 C13 C14 177.31(19) . . . . ?
C11 C13 C14 N4 1.5(2) . . . . ?
C12 N3 C8 C9 0.8(2) . . . . ?
C12 N4 C14 C13 -1.74(19) . . . . ?
C12 C11 C13 C14 -0.69(18) . . . . ?
C13 C11 C12 N3 179.39(14) . . . . ?
C13 C11 C12 N4 -0.39(17) . . . . ?
C14 N4 C12 N3 -178.48(15) . . . . ?
C14 N4 C12 C11 1.28(17) . . . . ?
C15 N5 C19 N6 -178.85(14) . . . . ?
C15 N5 C19 C18 2.4(2) . . . . ?
C15 C16 C17 C18 1.3(2) . . . . ?
C16 C17 C18 C19 -0.2(2) . . . . ?
C16 C17 C18 C20 -179.50(17) . . . . ?
C17 C18 C19 N5 -1.7(2) . . . . ?
C17 C18 C19 N6 179.38(13) . . . . ?
C17 C18 C20 C21 179.68(18) . . . . ?
C18 C20 C21 N6 0.54(18) . . . . ?
C19 N5 C15 C16 -1.2(2) . . . . ?
C19 N6 C21 C20 -1.24(18) . . . . ?
C19 C18 C20 C21 0.32(17) . . . . ?
C20 C18 C19 N5 177.82(13) . . . . ?
C20 C18 C19 N6 -1.11(16) . . . . ?
C21 N6 C19 N5 -177.42(14) . . . . ?
C21 N6 C19 C18 1.45(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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 2288063'
loop_
_audit_author_name
_audit_author_address
'Chris Hawes'
;Keele University
United Kingdom
;
_audit_update_record             
;
2023-08-10 deposited with the CCDC.	2023-11-01 downloaded from the CCDC.
;
_audit_creation_date             2023-08-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H18 Gd N9 O12'
_chemical_formula_sum            'C21 H18 Gd N9 O12'
_chemical_formula_weight         745.69
_chemical_melting_point          ?
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'
Gd Gd -0.1653 3.9035 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5744(3)
_cell_length_b                   11.7399(4)
_cell_length_c                   14.2153(5)
_cell_angle_alpha                78.6810(10)
_cell_angle_beta                 77.1570(10)
_cell_angle_gamma                70.8240(10)
_cell_volume                     1305.88(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9973
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      28.706
_cell_measurement_theta_min      2.524
_shelx_estimated_absorpt_T_max   0.622
_shelx_estimated_absorpt_T_min   0.560
_exptl_absorpt_coefficient_mu    2.622
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6210
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0559 before and 0.0371 after correction.
The Ratio of minimum to maximum transmission is 0.8327.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.896
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             734
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            27414
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.705
_diffrn_reflns_theta_min         3.163
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Quest ECO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6411
_reflns_number_total             6724
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.697
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         6724
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0192
_refine_ls_R_factor_gt           0.0174
_refine_ls_restrained_S_all      1.114
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0089P)²+1.0644P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0379
_refine_ls_wR_factor_ref         0.0384
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 N2-H2 = N4-H4 = N6-H6
 0.88 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3), C6(H6A), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13),
 C14(H14), C15(H15), C16(H16), C17(H17), C20(H20), C21(H21)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Gd1 Gd 0.47878(2) 0.69762(2) 0.71280(2) 0.01465(3) Uani 1 1 d . . . . .
O1 O 0.68787(16) 0.63854(11) 0.81002(9) 0.0200(3) Uani 1 1 d . . . . .
O2 O 0.70537(16) 0.73195(11) 0.59961(9) 0.0201(3) Uani 1 1 d . . . . .
O3 O 0.62139(16) 0.50098(11) 0.67655(9) 0.0202(3) Uani 1 1 d . . . . .
O4 O 0.29929(17) 0.82146(12) 0.83807(10) 0.0238(3) Uani 1 1 d . . . . .
O5 O 0.48108(17) 0.90146(12) 0.74380(10) 0.0246(3) Uani 1 1 d . . . . .
O6 O 0.2954(2) 1.00335(13) 0.85257(11) 0.0332(3) Uani 1 1 d . . . . .
O7 O 0.30530(18) 0.86148(12) 0.60984(10) 0.0259(3) Uani 1 1 d . . . . .
O8 O 0.40208(17) 0.68934(12) 0.55411(10) 0.0244(3) Uani 1 1 d . . . . .
O9 O 0.2038(2) 0.83378(17) 0.49163(12) 0.0458(4) Uani 1 1 d . . . . .
O10 O 0.21233(17) 0.65187(12) 0.74616(9) 0.0218(3) Uani 1 1 d . . . . .
O11 O 0.37082(16) 0.56245(12) 0.85407(10) 0.0224(3) Uani 1 1 d . . . . .
O12 O 0.11658(18) 0.55036(14) 0.87898(11) 0.0326(3) Uani 1 1 d . . . . .
N1 N 0.73466(19) 0.69963(13) 0.86411(11) 0.0191(3) Uani 1 1 d . . . . .
N2 N 0.8444(2) 0.81805(14) 0.72325(12) 0.0211(3) Uani 1 1 d D . . . .
H2 H 0.816(3) 0.792(2) 0.6784(14) 0.025 Uiso 1 1 d D U . . .
N3 N 0.76318(18) 0.74444(13) 0.50385(11) 0.0172(3) Uani 1 1 d . . . . .
N4 N 0.80243(19) 0.53491(13) 0.49148(11) 0.0189(3) Uani 1 1 d D . . . .
H4 H 0.755(3) 0.5132(19) 0.5495(12) 0.023 Uiso 1 1 d D U . . .
N5 N 0.60353(18) 0.39115(12) 0.71742(11) 0.0170(3) Uani 1 1 d . . . . .
N6 N 0.7327(2) 0.38650(14) 0.85229(12) 0.0214(3) Uani 1 1 d D . . . .
H6 H 0.736(3) 0.4598(15) 0.8421(16) 0.026 Uiso 1 1 d D U . . .
N7 N 0.3576(2) 0.91159(14) 0.81263(11) 0.0209(3) Uani 1 1 d . . . . .
N8 N 0.3011(2) 0.79636(15) 0.54932(12) 0.0253(3) Uani 1 1 d . . . . .
N9 N 0.22910(19) 0.58689(13) 0.82821(11) 0.0200(3) Uani 1 1 d . . . . .
C1 C 0.7134(2) 0.67447(17) 0.96223(14) 0.0237(4) Uani 1 1 d . . . . .
H1 H 0.662488 0.613356 0.994304 0.028 Uiso 1 1 calc R U . . .
C2 C 0.7651(3) 0.73666(19) 1.01620(15) 0.0277(4) Uani 1 1 d . . . . .
H2A H 0.749677 0.717443 1.085083 0.033 Uiso 1 1 calc R U . . .
C3 C 0.8391(2) 0.82683(18) 0.97161(15) 0.0258(4) Uani 1 1 d . . . . .
H3 H 0.872195 0.870629 1.009227 0.031 Uiso 1 1 calc R U . . .
C4 C 0.8635(2) 0.85147(17) 0.87121(15) 0.0221(4) Uani 1 1 d . . . . .
C5 C 0.8107(2) 0.78383(16) 0.81929(13) 0.0196(3) Uani 1 1 d . . . . .
C6 C 0.9305(2) 0.93306(18) 0.79781(15) 0.0258(4) Uani 1 1 d . . . . .
H6A H 0.976783 0.991882 0.808210 0.031 Uiso 1 1 calc R U . . .
C7 C 0.9159(2) 0.91110(17) 0.71066(15) 0.0251(4) Uani 1 1 d . . . . .
H7 H 0.949878 0.953564 0.649482 0.030 Uiso 1 1 calc R U . . .
C8 C 0.7798(2) 0.85221(16) 0.45556(14) 0.0215(4) Uani 1 1 d . . . . .
H8 H 0.742889 0.921548 0.488867 0.026 Uiso 1 1 calc R U . . .
C9 C 0.8500(2) 0.86220(17) 0.35804(14) 0.0246(4) Uani 1 1 d . . . . .
H9 H 0.859729 0.938931 0.325285 0.030 Uiso 1 1 calc R U . . .
C10 C 0.9066(2) 0.76345(17) 0.30684(14) 0.0234(4) Uani 1 1 d . . . . .
H10 H 0.956352 0.771019 0.240073 0.028 Uiso 1 1 calc R U . . .
C11 C 0.8881(2) 0.65225(16) 0.35647(13) 0.0193(3) Uani 1 1 d . . . . .
C12 C 0.8137(2) 0.64754(15) 0.45549(13) 0.0169(3) Uani 1 1 d . . . . .
C13 C 0.9226(2) 0.53257(17) 0.33361(14) 0.0229(4) Uani 1 1 d . . . . .
H13 H 0.973504 0.505058 0.272330 0.028 Uiso 1 1 calc R U . . .
C14 C 0.8690(2) 0.46529(17) 0.41606(14) 0.0223(4) Uani 1 1 d . . . . .
H14 H 0.876248 0.381862 0.421160 0.027 Uiso 1 1 calc R U . . .
C15 C 0.5325(2) 0.33236(17) 0.67547(14) 0.0223(4) Uani 1 1 d . . . . .
H15 H 0.490327 0.369397 0.616853 0.027 Uiso 1 1 calc R U . . .
C16 C 0.5204(2) 0.21808(17) 0.71720(15) 0.0256(4) Uani 1 1 d . . . . .
H16 H 0.469392 0.177774 0.686802 0.031 Uiso 1 1 calc R U . . .
C17 C 0.5811(2) 0.16131(17) 0.80223(15) 0.0257(4) Uani 1 1 d . . . . .
H17 H 0.573478 0.082497 0.830230 0.031 Uiso 1 1 calc R U . . .
C18 C 0.6536(2) 0.22287(16) 0.84543(13) 0.0219(4) Uani 1 1 d . . . . .
C19 C 0.6614(2) 0.33920(15) 0.80058(13) 0.0181(3) Uani 1 1 d . . . . .
C20 C 0.7258(3) 0.20189(18) 0.93105(14) 0.0291(4) Uani 1 1 d . . . . .
H20 H 0.740936 0.130688 0.977551 0.035 Uiso 1 1 calc R U . . .
C21 C 0.7685(3) 0.30243(18) 0.93358(15) 0.0283(4) Uani 1 1 d . . . . .
H21 H 0.816335 0.313630 0.984015 0.034 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Gd1 O1 2.3482(12) . ?
Gd1 O2 2.3230(12) . ?
Gd1 O3 2.3286(12) . ?
Gd1 O4 2.4457(13) . ?
Gd1 O5 2.5240(13) . ?
Gd1 O7 2.4573(13) . ?
Gd1 O8 2.5136(13) . ?
Gd1 O10 2.4408(13) . ?
Gd1 O11 2.5091(13) . ?
O1 N1 1.3449(19) . ?
O2 N3 1.3378(19) . ?
O3 N5 1.3489(18) . ?
O4 N7 1.272(2) . ?
O5 N7 1.263(2) . ?
O6 N7 1.223(2) . ?
O7 N8 1.271(2) . ?
O8 N8 1.269(2) . ?
O9 N8 1.218(2) . ?
O10 N9 1.2713(19) . ?
O11 N9 1.274(2) . ?
O12 N9 1.215(2) . ?
N1 C1 1.351(2) . ?
N1 C5 1.342(2) . ?
N2 H2 0.867(15) . ?
N2 C5 1.339(2) . ?
N2 C7 1.384(2) . ?
N3 C8 1.351(2) . ?
N3 C12 1.344(2) . ?
N4 H4 0.865(15) . ?
N4 C12 1.348(2) . ?
N4 C14 1.382(2) . ?
N5 C15 1.342(2) . ?
N5 C19 1.340(2) . ?
N6 H6 0.853(15) . ?
N6 C19 1.344(2) . ?
N6 C21 1.384(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.379(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.387(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.382(3) . ?
C4 C5 1.412(3) . ?
C4 C6 1.428(3) . ?
C6 H6A 0.9500 . ?
C6 C7 1.354(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.382(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.383(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.397(3) . ?
C11 C12 1.409(2) . ?
C11 C13 1.425(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.358(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C15 C16 1.384(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.383(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.387(3) . ?
C18 C19 1.405(2) . ?
C18 C20 1.429(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.355(3) . ?
C21 H21 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Gd1 O4 87.11(5) . . ?
O1 Gd1 O5 78.71(4) . . ?
O1 Gd1 O7 147.59(4) . . ?
O1 Gd1 O8 147.12(4) . . ?
O1 Gd1 O10 128.75(4) . . ?
O1 Gd1 O11 77.20(4) . . ?
O2 Gd1 O1 78.81(5) . . ?
O2 Gd1 O3 79.44(4) . . ?
O2 Gd1 O4 128.60(4) . . ?
O2 Gd1 O5 77.33(4) . . ?
O2 Gd1 O7 85.50(5) . . ?
O2 Gd1 O8 77.37(5) . . ?
O2 Gd1 O10 148.50(4) . . ?
O2 Gd1 O11 148.06(4) . . ?
O3 Gd1 O1 78.85(4) . . ?
O3 Gd1 O4 145.59(4) . . ?
O3 Gd1 O5 150.30(5) . . ?
O3 Gd1 O7 126.01(4) . . ?
O3 Gd1 O8 74.78(4) . . ?
O3 Gd1 O10 90.52(5) . . ?
O3 Gd1 O11 75.49(4) . . ?
O4 Gd1 O5 51.38(4) . . ?
O4 Gd1 O7 80.77(5) . . ?
O4 Gd1 O8 125.59(5) . . ?
O4 Gd1 O11 70.79(4) . . ?
O7 Gd1 O5 70.21(5) . . ?
O7 Gd1 O8 51.31(4) . . ?
O7 Gd1 O11 125.42(4) . . ?
O8 Gd1 O5 117.20(4) . . ?
O10 Gd1 O4 74.04(4) . . ?
O10 Gd1 O5 118.78(4) . . ?
O10 Gd1 O7 76.41(4) . . ?
O10 Gd1 O8 71.19(4) . . ?
O10 Gd1 O11 51.69(4) . . ?
O11 Gd1 O5 117.71(4) . . ?
O11 Gd1 O8 113.95(4) . . ?
N1 O1 Gd1 132.53(10) . . ?
N3 O2 Gd1 142.11(11) . . ?
N5 O3 Gd1 132.72(10) . . ?
N7 O4 Gd1 97.70(10) . . ?
N7 O5 Gd1 94.21(10) . . ?
N8 O7 Gd1 97.05(10) . . ?
N8 O8 Gd1 94.43(10) . . ?
N9 O10 Gd1 97.60(10) . . ?
N9 O11 Gd1 94.27(10) . . ?
O1 N1 C1 121.54(15) . . ?
C5 N1 O1 119.14(15) . . ?
C5 N1 C1 119.25(16) . . ?
C5 N2 H2 125.9(15) . . ?
C5 N2 C7 106.94(16) . . ?
C7 N2 H2 126.8(15) . . ?
O2 N3 C8 120.85(15) . . ?
O2 N3 C12 119.92(14) . . ?
C12 N3 C8 119.15(15) . . ?
C12 N4 H4 125.7(15) . . ?
C12 N4 C14 106.84(15) . . ?
C14 N4 H4 127.3(15) . . ?
C15 N5 O3 121.39(15) . . ?
C19 N5 O3 118.89(14) . . ?
C19 N5 C15 119.70(15) . . ?
C19 N6 H6 125.2(15) . . ?
C19 N6 C21 106.82(16) . . ?
C21 N6 H6 126.9(15) . . ?
O5 N7 O4 116.52(14) . . ?
O6 N7 O4 121.25(16) . . ?
O6 N7 O5 122.23(16) . . ?
O8 N8 O7 115.88(15) . . ?
O9 N8 O7 121.93(17) . . ?
O9 N8 O8 122.18(17) . . ?
O10 N9 O11 116.02(14) . . ?
O12 N9 O10 121.99(16) . . ?
O12 N9 O11 121.98(16) . . ?
N1 C1 H1 119.7 . . ?
N1 C1 C2 120.62(18) . . ?
C2 C1 H1 119.7 . . ?
C1 C2 H2A 119.4 . . ?
C1 C2 C3 121.10(19) . . ?
C3 C2 H2A 119.4 . . ?
C2 C3 H3 120.8 . . ?
C4 C3 C2 118.46(18) . . ?
C4 C3 H3 120.8 . . ?
C3 C4 C5 118.17(18) . . ?
C3 C4 C6 137.24(18) . . ?
C5 C4 C6 104.59(17) . . ?
N1 C5 C4 122.34(17) . . ?
N2 C5 N1 126.98(17) . . ?
N2 C5 C4 110.67(17) . . ?
C4 C6 H6A 126.3 . . ?
C7 C6 C4 107.34(17) . . ?
C7 C6 H6A 126.3 . . ?
N2 C7 H7 124.8 . . ?
C6 C7 N2 110.43(18) . . ?
C6 C7 H7 124.8 . . ?
N3 C8 H8 119.8 . . ?
N3 C8 C9 120.43(17) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 119.1 . . ?
C8 C9 C10 121.75(17) . . ?
C10 C9 H9 119.1 . . ?
C9 C10 H10 121.1 . . ?
C9 C10 C11 117.86(17) . . ?
C11 C10 H10 121.1 . . ?
C10 C11 C12 118.03(16) . . ?
C10 C11 C13 136.79(17) . . ?
C12 C11 C13 105.17(16) . . ?
N3 C12 N4 126.90(16) . . ?
N3 C12 C11 122.76(16) . . ?
N4 C12 C11 110.34(15) . . ?
C11 C13 H13 126.5 . . ?
C14 C13 C11 107.00(16) . . ?
C14 C13 H13 126.5 . . ?
N4 C14 H14 124.7 . . ?
C13 C14 N4 110.64(16) . . ?
C13 C14 H14 124.7 . . ?
N5 C15 H15 119.8 . . ?
N5 C15 C16 120.30(18) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 119.3 . . ?
C17 C16 C15 121.36(18) . . ?
C17 C16 H16 119.3 . . ?
C16 C17 H17 121.0 . . ?
C16 C17 C18 118.00(17) . . ?
C18 C17 H17 121.0 . . ?
C17 C18 C19 118.39(17) . . ?
C17 C18 C20 136.84(18) . . ?
C19 C18 C20 104.74(17) . . ?
N5 C19 N6 127.03(16) . . ?
N5 C19 C18 122.22(17) . . ?
N6 C19 C18 110.75(16) . . ?
C18 C20 H20 126.4 . . ?
C21 C20 C18 107.27(17) . . ?
C21 C20 H20 126.4 . . ?
N6 C21 H21 124.8 . . ?
C20 C21 N6 110.38(18) . . ?
C20 C21 H21 124.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 O2 0.867(15) 1.969(16) 2.820(2) 167(2) . yes
N4 H4 O3 0.865(15) 1.917(16) 2.769(2) 168(2) . yes
N6 H6 O1 0.853(15) 1.980(16) 2.815(2) 166(2) . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Gd1 O1 N1 C1 113.09(17) . . . . ?
Gd1 O1 N1 C5 -69.8(2) . . . . ?
Gd1 O2 N3 C8 112.96(18) . . . . ?
Gd1 O2 N3 C12 -70.5(2) . . . . ?
Gd1 O3 N5 C15 104.28(17) . . . . ?
Gd1 O3 N5 C19 -77.12(19) . . . . ?
Gd1 O4 N7 O5 -4.30(16) . . . . ?
Gd1 O4 N7 O6 174.99(15) . . . . ?
Gd1 O5 N7 O4 4.14(15) . . . . ?
Gd1 O5 N7 O6 -175.15(15) . . . . ?
Gd1 O7 N8 O8 -11.57(17) . . . . ?
Gd1 O7 N8 O9 167.06(17) . . . . ?
Gd1 O8 N8 O7 11.25(16) . . . . ?
Gd1 O8 N8 O9 -167.37(18) . . . . ?
Gd1 O10 N9 O11 -6.50(15) . . . . ?
Gd1 O10 N9 O12 173.44(15) . . . . ?
Gd1 O11 N9 O10 6.29(15) . . . . ?
Gd1 O11 N9 O12 -173.66(15) . . . . ?
O1 N1 C1 C2 178.81(17) . . . . ?
O1 N1 C5 N2 1.6(3) . . . . ?
O1 N1 C5 C4 -179.95(15) . . . . ?
O2 N3 C8 C9 175.66(17) . . . . ?
O2 N3 C12 N4 5.2(3) . . . . ?
O2 N3 C12 C11 -174.80(16) . . . . ?
O3 N5 C15 C16 177.93(16) . . . . ?
O3 N5 C19 N6 2.6(3) . . . . ?
O3 N5 C19 C18 -177.35(15) . . . . ?
N1 C1 C2 C3 0.3(3) . . . . ?
N3 C8 C9 C10 -0.5(3) . . . . ?
N5 C15 C16 C17 -0.3(3) . . . . ?
C1 N1 C5 N2 178.70(17) . . . . ?
C1 N1 C5 C4 -2.8(3) . . . . ?
C1 C2 C3 C4 -1.4(3) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C2 C3 C4 C6 179.4(2) . . . . ?
C3 C4 C5 N1 1.7(3) . . . . ?
C3 C4 C5 N2 -179.54(17) . . . . ?
C3 C4 C6 C7 -179.4(2) . . . . ?
C4 C6 C7 N2 -0.7(2) . . . . ?
C5 N1 C1 C2 1.7(3) . . . . ?
C5 N2 C7 C6 1.4(2) . . . . ?
C5 C4 C6 C7 -0.2(2) . . . . ?
C6 C4 C5 N1 -177.62(16) . . . . ?
C6 C4 C5 N2 1.1(2) . . . . ?
C7 N2 C5 N1 177.10(17) . . . . ?
C7 N2 C5 C4 -1.5(2) . . . . ?
C8 N3 C12 N4 -178.17(17) . . . . ?
C8 N3 C12 C11 1.8(3) . . . . ?
C8 C9 C10 C11 1.0(3) . . . . ?
C9 C10 C11 C12 -0.2(3) . . . . ?
C9 C10 C11 C13 178.1(2) . . . . ?
C10 C11 C12 N3 -1.2(3) . . . . ?
C10 C11 C12 N4 178.75(16) . . . . ?
C10 C11 C13 C14 -178.2(2) . . . . ?
C11 C13 C14 N4 -0.4(2) . . . . ?
C12 N3 C8 C9 -0.9(3) . . . . ?
C12 N4 C14 C13 0.4(2) . . . . ?
C12 C11 C13 C14 0.3(2) . . . . ?
C13 C11 C12 N3 179.96(16) . . . . ?
C13 C11 C12 N4 0.0(2) . . . . ?
C14 N4 C12 N3 179.80(17) . . . . ?
C14 N4 C12 C11 -0.2(2) . . . . ?
C15 N5 C19 N6 -178.79(17) . . . . ?
C15 N5 C19 C18 1.3(3) . . . . ?
C15 C16 C17 C18 0.6(3) . . . . ?
C16 C17 C18 C19 0.0(3) . . . . ?
C16 C17 C18 C20 178.1(2) . . . . ?
C17 C18 C19 N5 -0.9(3) . . . . ?
C17 C18 C19 N6 179.13(16) . . . . ?
C17 C18 C20 C21 -177.4(2) . . . . ?
C18 C20 C21 N6 -1.9(2) . . . . ?
C19 N5 C15 C16 -0.7(3) . . . . ?
C19 N6 C21 C20 2.2(2) . . . . ?
C19 C18 C20 C21 0.9(2) . . . . ?
C20 C18 C19 N5 -179.57(17) . . . . ?
C20 C18 C19 N6 0.5(2) . . . . ?
C21 N6 C19 N5 178.46(18) . . . . ?
C21 N6 C19 C18 -1.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_Cu2L2OMe2
_database_code_depnum_ccdc_archive 'CCDC 2288066'
loop_
_audit_author_name
_audit_author_address
'Chris Hawes'
;Keele University
United Kingdom
;
_audit_update_record             
;
2023-08-10 deposited with the CCDC.	2023-11-01 downloaded from the CCDC.
;
_audit_creation_date             2023-08-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 Cu2 N4 O4'
_chemical_formula_sum            'C16 H16 Cu2 N4 O4'
_chemical_formula_weight         455.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.4309(6)
_cell_length_b                   10.4129(5)
_cell_length_c                   13.1342(6)
_cell_angle_alpha                90
_cell_angle_beta                 104.761(2)
_cell_angle_gamma                90
_cell_volume                     1644.00(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5121
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      28.256
_cell_measurement_theta_min      2.530
_shelx_estimated_absorpt_T_max   0.949
_shelx_estimated_absorpt_T_min   0.859
_exptl_absorpt_coefficient_mu    2.619
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0763 before and 0.0670 after correction.
The Ratio of minimum to maximum transmission is 0.8880.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.840
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1167
_diffrn_reflns_av_unetI/netI     0.0742
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            33543
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.285
_diffrn_reflns_theta_min         2.808
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Quest ECO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2816
_reflns_number_total             4084
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.820
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.127
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4084
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1063
_refine_ls_R_factor_gt           0.0632
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0302P)²+3.7936P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1104
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13),
 C14(H14)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.54993(5) 0.55304(5) 0.70696(4) 0.02115(16) Uani 1 1 d . . . . .
Cu2 Cu 0.38592(5) 0.57332(5) 0.49677(4) 0.01934(15) Uani 1 1 d . . . . .
O1 O 0.5401(3) 0.4806(3) 0.8444(3) 0.0320(8) Uani 1 1 d . . . . .
O2 O 0.3937(3) 0.6619(3) 0.3631(3) 0.0277(8) Uani 1 1 d . . . . .
O3 O 0.5408(3) 0.6156(3) 0.5650(2) 0.0199(7) Uani 1 1 d . . . . .
O4 O 0.3986(3) 0.5187(3) 0.6385(2) 0.0224(7) Uani 1 1 d . . . . .
N1 N 0.6993(3) 0.6029(4) 0.7828(3) 0.0259(9) Uani 1 1 d . . . . .
N2 N 0.6390(4) 0.4915(4) 0.9129(3) 0.0284(10) Uani 1 1 d . . . . .
N3 N 0.2259(3) 0.5582(4) 0.4279(3) 0.0245(9) Uani 1 1 d . . . . .
N4 N 0.2892(3) 0.6811(4) 0.3047(3) 0.0248(9) Uani 1 1 d . . . . .
C1 C 0.7997(4) 0.6572(5) 0.7807(4) 0.0309(12) Uani 1 1 d . . . . .
H1 H 0.812815 0.699807 0.721017 0.037 Uiso 1 1 calc R U . . .
C2 C 0.8790(4) 0.6429(5) 0.8747(4) 0.0327(13) Uani 1 1 d . . . . .
H2 H 0.953405 0.673383 0.890523 0.039 Uiso 1 1 calc R U . . .
C3 C 0.8284(4) 0.5740(5) 0.9433(4) 0.0303(12) Uani 1 1 d . . . . .
C4 C 0.7189(4) 0.5531(4) 0.8795(4) 0.0249(11) Uani 1 1 d . . . . .
C5 C 0.8525(5) 0.5203(5) 1.0429(4) 0.0335(13) Uani 1 1 d . . . . .
H5 H 0.925144 0.527144 1.088405 0.040 Uiso 1 1 calc R U . . .
C6 C 0.7696(5) 0.4566(5) 1.0755(4) 0.0362(13) Uani 1 1 d . . . . .
H6 H 0.786255 0.420873 1.144305 0.043 Uiso 1 1 calc R U . . .
C7 C 0.6625(5) 0.4431(5) 1.0110(4) 0.0302(11) Uani 1 1 d . . . . .
H7 H 0.606687 0.400186 1.035870 0.036 Uiso 1 1 calc R U . . .
C8 C 0.1215(4) 0.5214(5) 0.4326(4) 0.0287(12) Uani 1 1 d . . . . .
H8 H 0.107331 0.468839 0.486905 0.034 Uiso 1 1 calc R U . . .
C9 C 0.0396(4) 0.5687(5) 0.3506(4) 0.0298(11) Uani 1 1 d . . . . .
H9 H -0.038228 0.555324 0.338981 0.036 Uiso 1 1 calc R U . . .
C10 C 0.0932(4) 0.6417(4) 0.2859(4) 0.0260(11) Uani 1 1 d . . . . .
C11 C 0.2070(4) 0.6291(4) 0.3399(4) 0.0189(10) Uani 1 1 d . . . . .
C12 C 0.0681(4) 0.7139(5) 0.1949(4) 0.0302(12) Uani 1 1 d . . . . .
H12 H -0.006945 0.727997 0.156994 0.036 Uiso 1 1 calc R U . . .
C13 C 0.1558(5) 0.7654(5) 0.1602(4) 0.0336(13) Uani 1 1 d . . . . .
H13 H 0.139614 0.813887 0.096867 0.040 Uiso 1 1 calc R U . . .
C14 C 0.2660(4) 0.7484(4) 0.2150(4) 0.0247(11) Uani 1 1 d . . . . .
H14 H 0.324230 0.784070 0.189195 0.030 Uiso 1 1 calc R U . . .
C15 C 0.5959(4) 0.7274(4) 0.5437(4) 0.0267(11) Uani 1 1 d . . . . .
H15A H 0.567200 0.751334 0.469573 0.040 Uiso 1 1 calc R U . . .
H15B H 0.675926 0.710662 0.558278 0.040 Uiso 1 1 calc R U . . .
H15C H 0.582667 0.797821 0.588574 0.040 Uiso 1 1 calc R U . . .
C16 C 0.3324(5) 0.4265(5) 0.6724(4) 0.0328(12) Uani 1 1 d . . . . .
H16A H 0.294712 0.466493 0.721384 0.049 Uiso 1 1 calc R U . . .
H16B H 0.379558 0.356086 0.707865 0.049 Uiso 1 1 calc R U . . .
H16C H 0.276747 0.392875 0.611367 0.049 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.989(3) . ?
Cu1 O3 1.951(3) . ?
Cu1 O4 1.901(3) . ?
Cu1 N1 1.941(4) . ?
Cu2 O2 2.007(3) . ?
Cu2 O3 1.955(3) . ?
Cu2 O4 1.915(3) . ?
Cu2 N3 1.970(4) . ?
O1 N2 1.330(5) . ?
O2 N4 1.344(5) . ?
O3 C15 1.415(5) . ?
O4 C16 1.408(5) . ?
N1 C1 1.376(6) . ?
N1 C4 1.336(6) . ?
N2 C4 1.347(6) . ?
N2 C7 1.345(6) . ?
N3 C8 1.370(6) . ?
N3 C11 1.340(6) . ?
N4 C11 1.339(6) . ?
N4 C14 1.337(6) . ?
C1 H1 0.9500 . ?
C1 C2 1.378(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.418(7) . ?
C3 C4 1.422(7) . ?
C3 C5 1.384(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.382(7) . ?
C6 H6 0.9500 . ?
C6 C7 1.391(7) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.372(7) . ?
C9 H9 0.9500 . ?
C9 C10 1.426(7) . ?
C10 C11 1.417(6) . ?
C10 C12 1.379(7) . ?
C12 H12 0.9500 . ?
C12 C13 1.392(7) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(7) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Cu1 O1 172.79(14) . . ?
O4 Cu1 O1 94.32(14) . . ?
O4 Cu1 O3 78.53(13) . . ?
O4 Cu1 N1 174.36(15) . . ?
N1 Cu1 O1 84.72(16) . . ?
N1 Cu1 O3 102.49(15) . . ?
O3 Cu2 O2 92.07(13) . . ?
O3 Cu2 N3 171.54(15) . . ?
O4 Cu2 O2 167.61(14) . . ?
O4 Cu2 O3 78.11(13) . . ?
O4 Cu2 N3 104.24(15) . . ?
N3 Cu2 O2 84.43(15) . . ?
N2 O1 Cu1 108.7(3) . . ?
N4 O2 Cu2 108.2(3) . . ?
Cu1 O3 Cu2 100.01(13) . . ?
C15 O3 Cu1 123.4(3) . . ?
C15 O3 Cu2 124.4(3) . . ?
Cu1 O4 Cu2 103.30(14) . . ?
C16 O4 Cu1 124.5(3) . . ?
C16 O4 Cu2 126.8(3) . . ?
C1 N1 Cu1 148.6(4) . . ?
C4 N1 Cu1 107.6(3) . . ?
C4 N1 C1 103.4(4) . . ?
O1 N2 C4 116.9(4) . . ?
O1 N2 C7 123.6(4) . . ?
C7 N2 C4 119.5(5) . . ?
C8 N3 Cu2 149.2(4) . . ?
C11 N3 Cu2 106.7(3) . . ?
C11 N3 C8 103.5(4) . . ?
C11 N4 O2 117.0(4) . . ?
C14 N4 O2 122.8(4) . . ?
C14 N4 C11 120.2(4) . . ?
N1 C1 H1 123.8 . . ?
N1 C1 C2 112.5(5) . . ?
C2 C1 H1 123.8 . . ?
C1 C2 H2 126.5 . . ?
C1 C2 C3 107.0(5) . . ?
C3 C2 H2 126.5 . . ?
C2 C3 C4 102.5(5) . . ?
C5 C3 C2 141.4(5) . . ?
C5 C3 C4 116.1(5) . . ?
N1 C4 N2 121.6(5) . . ?
N1 C4 C3 114.6(4) . . ?
N2 C4 C3 123.8(5) . . ?
C3 C5 H5 120.4 . . ?
C6 C5 C3 119.2(5) . . ?
C6 C5 H5 120.4 . . ?
C5 C6 H6 118.9 . . ?
C5 C6 C7 122.2(5) . . ?
C7 C6 H6 118.9 . . ?
N2 C7 C6 119.1(5) . . ?
N2 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
N3 C8 H8 123.6 . . ?
N3 C8 C9 112.7(5) . . ?
C9 C8 H8 123.6 . . ?
C8 C9 H9 126.5 . . ?
C8 C9 C10 107.0(5) . . ?
C10 C9 H9 126.5 . . ?
C11 C10 C9 102.2(4) . . ?
C12 C10 C9 140.3(5) . . ?
C12 C10 C11 117.5(4) . . ?
N3 C11 C10 114.6(4) . . ?
N4 C11 N3 122.6(4) . . ?
N4 C11 C10 122.8(4) . . ?
C10 C12 H12 121.0 . . ?
C10 C12 C13 118.0(5) . . ?
C13 C12 H12 121.0 . . ?
C12 C13 H13 118.9 . . ?
C14 C13 C12 122.2(5) . . ?
C14 C13 H13 118.9 . . ?
N4 C14 C13 119.2(5) . . ?
N4 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 N2 C4 4.0(5) . . . . ?
Cu1 O1 N2 C7 -174.9(4) . . . . ?
Cu1 N1 C1 C2 -171.7(5) . . . . ?
Cu1 N1 C4 N2 -5.6(5) . . . . ?
Cu1 N1 C4 C3 176.1(3) . . . . ?
Cu2 O2 N4 C11 -6.2(4) . . . . ?
Cu2 O2 N4 C14 173.8(3) . . . . ?
Cu2 N3 C8 C9 167.3(5) . . . . ?
Cu2 N3 C11 N4 8.5(5) . . . . ?
Cu2 N3 C11 C10 -173.1(3) . . . . ?
O1 N2 C4 N1 1.1(6) . . . . ?
O1 N2 C4 C3 179.3(4) . . . . ?
O1 N2 C7 C6 178.2(4) . . . . ?
O2 N4 C11 N3 -1.6(6) . . . . ?
O2 N4 C11 C10 -179.9(4) . . . . ?
O2 N4 C14 C13 -179.0(4) . . . . ?
N1 C1 C2 C3 0.4(6) . . . . ?
N3 C8 C9 C10 0.4(6) . . . . ?
C1 N1 C4 N2 179.4(4) . . . . ?
C1 N1 C4 C3 1.1(5) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C1 C2 C3 C5 176.3(6) . . . . ?
C2 C3 C4 N1 -0.9(5) . . . . ?
C2 C3 C4 N2 -179.1(4) . . . . ?
C2 C3 C5 C6 -178.7(6) . . . . ?
C3 C5 C6 C7 0.8(8) . . . . ?
C4 N1 C1 C2 -0.9(5) . . . . ?
C4 N2 C7 C6 -0.7(7) . . . . ?
C4 C3 C5 C6 -3.0(7) . . . . ?
C5 C3 C4 N1 -178.1(4) . . . . ?
C5 C3 C4 N2 3.6(7) . . . . ?
C5 C6 C7 N2 1.2(8) . . . . ?
C7 N2 C4 N1 -179.9(4) . . . . ?
C7 N2 C4 C3 -1.8(7) . . . . ?
C8 N3 C11 N4 -178.0(4) . . . . ?
C8 N3 C11 C10 0.4(5) . . . . ?
C8 C9 C10 C11 -0.1(5) . . . . ?
C8 C9 C10 C12 179.9(6) . . . . ?
C9 C10 C11 N3 -0.2(5) . . . . ?
C9 C10 C11 N4 178.3(4) . . . . ?
C9 C10 C12 C13 -177.8(6) . . . . ?
C10 C12 C13 C14 -1.2(8) . . . . ?
C11 N3 C8 C9 -0.5(5) . . . . ?
C11 N4 C14 C13 1.1(7) . . . . ?
C11 C10 C12 C13 2.3(7) . . . . ?
C12 C10 C11 N3 179.8(4) . . . . ?
C12 C10 C11 N4 -1.8(7) . . . . ?
C12 C13 C14 N4 -0.5(7) . . . . ?
C14 N4 C11 N3 178.4(4) . . . . ?
C14 N4 C11 C10 0.1(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
