# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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. 
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data_1
_database_code_depnum_ccdc_archive 'CCDC 1871949'
_audit_update_record             
;
2018-11-13 deposited with the CCDC.
2018-11-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H36 N10 O22 Tb2'
_chemical_formula_weight         1326.63

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'
Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.648(2)
_cell_length_b                   18.182(4)
_cell_length_c                   12.408(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.205(3)
_cell_angle_gamma                90
_cell_volume                     2254.4(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6051
_cell_measurement_theta_min      3.0294
_cell_measurement_theta_max      27.4855

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.954
_exptl_crystal_F_000             1304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.211
_shelx_estimated_absorpt_T_min   0.644
_shelx_estimated_absorpt_T_max   0.740
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8631
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   '(Higashi, 1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn 724+'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18090
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.003
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5109
_reflns_number_gt                4217
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        
'CrystalClear (Rigaku Inc., 2008), SORTAV (Blessing, 1995)'
_computing_structure_solution    'SIR92 (Altomare et al, 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0400P)²+0.0200P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5109
_refine_ls_number_parameters     344
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0767
_refine_ls_wR_factor_gt          0.0708
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Tb1 Tb 0.88067(2) 0.52338(2) 0.34362(2) 0.01336(7) Uani 1 1 d . . . . .
O10 O 0.9980(3) 0.45977(16) 0.2282(3) 0.0228(7) Uani 1 1 d . . . . .
N2 N 1.1207(3) 0.5778(2) 0.1393(3) 0.0178(7) Uani 1 1 d D . . . .
O7 O 0.7154(3) 0.48823(16) 0.1592(2) 0.0214(6) Uani 1 1 d . . . . .
O1 O 0.8969(3) 0.47536(14) 0.5238(2) 0.0133(5) Uani 1 1 d . . . . .
O6 O 0.6649(3) 0.45391(16) 0.3063(2) 0.0204(6) Uani 1 1 d . . . . .
C20 C 1.2190(5) 0.4755(2) 0.0716(4) 0.0258(10) Uani 1 1 d . . . . .
H10A H 1.1662 0.4480 0.1090 0.039 Uiso 1 1 calc R U . . .
H10B H 1.3130 0.4604 0.1042 0.039 Uiso 1 1 calc R U . . .
H10C H 1.1851 0.4651 -0.0110 0.039 Uiso 1 1 calc R U . . .
O3 O 0.6954(3) 0.61010(17) 0.3032(3) 0.0248(7) Uani 1 1 d . . . . .
O2 O 0.9443(3) 0.60850(15) 0.2448(2) 0.0184(6) Uani 1 1 d . . . . .
C3 C 0.6123(4) 0.4832(3) 0.6284(4) 0.0246(10) Uani 1 1 d . . . . .
H13 H 0.5627 0.5187 0.6532 0.030 Uiso 1 1 calc R U . . .
O8 O 0.5369(3) 0.4223(2) 0.1346(3) 0.0332(8) Uani 1 1 d . . . . .
O4 O 0.8697(3) 0.64093(16) 0.4486(2) 0.0246(7) Uani 1 1 d . . . . .
C2 C 0.7180(4) 0.5069(2) 0.5925(4) 0.0190(9) Uani 1 1 d . . . . .
H12 H 0.7390 0.5578 0.5942 0.023 Uiso 1 1 calc R U . . .
N4 N 0.6349(3) 0.4538(2) 0.1983(3) 0.0211(8) Uani 1 1 d . . . . .
O9 O 0.9172(3) 0.38801(16) 0.3257(2) 0.0213(6) Uani 1 1 d . . . . .
C7 C 0.6237(4) 0.2818(3) 0.5842(4) 0.0269(10) Uani 1 1 d . . . . .
H17 H 0.5569 0.2634 0.6117 0.032 Uiso 1 1 calc R U . . .
C8 C 0.6939(5) 0.2339(2) 0.5414(4) 0.0296(11) Uani 1 1 d . . . . .
H18 H 0.6762 0.1827 0.5412 0.035 Uiso 1 1 calc R U . . .
O5 O 0.7120(4) 0.7210(2) 0.3708(3) 0.0462(10) Uani 1 1 d . . . . .
O11 O 1.0381(3) 0.34150(18) 0.2314(3) 0.0385(9) Uani 1 1 d . . . . .
C18 C 1.2851(4) 0.6101(3) 0.0611(4) 0.0250(10) Uani 1 1 d . . . . .
H8 H 1.3491 0.5959 0.0274 0.030 Uiso 1 1 calc R U . . .
C16 C 1.0992(4) 0.6496(2) 0.1612(3) 0.0165(8) Uani 1 1 d . . . . .
C1 C 0.7910(4) 0.4567(2) 0.5552(3) 0.0159(8) Uani 1 1 d . . . . .
N1 N 0.8173(3) 0.33128(19) 0.5042(3) 0.0193(7) Uani 1 1 d D . . . .
C10 C 0.8693(5) 0.2107(2) 0.4473(4) 0.0314(11) Uani 1 1 d . . . . .
H20A H 0.9052 0.2399 0.3982 0.047 Uiso 1 1 calc R U . . .
H20B H 0.8105 0.1722 0.4014 0.047 Uiso 1 1 calc R U . . .
H20C H 0.9433 0.1881 0.5090 0.047 Uiso 1 1 calc R U . . .
C19 C 1.2079(4) 0.5557(2) 0.0908(3) 0.0213(9) Uani 1 1 d . . . . .
N5 N 0.9860(3) 0.39399(19) 0.2600(3) 0.0212(8) Uani 1 1 d . . . . .
C13 C 1.0559(5) 0.7941(2) 0.2033(4) 0.0260(10) Uani 1 1 d . . . . .
H3 H 1.0395 0.8438 0.2175 0.031 Uiso 1 1 calc R U . . .
C17 C 1.2686(4) 0.6826(3) 0.0801(4) 0.0264(10) Uani 1 1 d . . . . .
H7 H 1.3219 0.7184 0.0602 0.032 Uiso 1 1 calc R U . . .
C11 C 1.0050(4) 0.6649(2) 0.2172(3) 0.0168(8) Uani 1 1 d . . . . .
C12 C 0.9857(4) 0.7383(2) 0.2367(3) 0.0213(9) Uani 1 1 d . . . . .
H2 H 0.9239 0.7513 0.2734 0.026 Uiso 1 1 calc R U . . .
N3 N 0.7571(4) 0.6597(2) 0.3741(3) 0.0251(8) Uani 1 1 d . . . . .
C15 C 1.1727(4) 0.7055(2) 0.1292(4) 0.0218(9) Uani 1 1 d . . . . .
C6 C 0.7525(4) 0.3821(2) 0.5488(3) 0.0163(8) Uani 1 1 d . . . . .
C4 C 0.5799(4) 0.4113(3) 0.6281(4) 0.0260(10) Uani 1 1 d . . . . .
H14 H 0.5103 0.3966 0.6551 0.031 Uiso 1 1 calc R U . . .
C5 C 0.6491(4) 0.3584(3) 0.5881(3) 0.0219(9) Uani 1 1 d . . . . .
C9 C 0.7918(4) 0.2592(2) 0.4978(4) 0.0240(10) Uani 1 1 d . . . . .
C14 C 1.1469(4) 0.7793(2) 0.1511(4) 0.0251(10) Uani 1 1 d . . . . .
H4 H 1.1926 0.8183 0.1296 0.030 Uiso 1 1 calc R U . . .
H1A H 1.085(4) 0.545(2) 0.166(4) 0.022(13) Uiso 1 1 d D . . . .
H2A H 0.880(3) 0.346(3) 0.481(4) 0.035(15) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Tb1 O2 2.221(3) . ?
Tb1 O1 2.350(3) . ?
Tb1 O1 2.372(3) 3_766 ?
Tb1 O3 2.438(3) . ?
Tb1 O7 2.441(3) . ?
Tb1 O10 2.487(3) . ?
Tb1 O9 2.514(3) . ?
Tb1 O6 2.521(3) . ?
Tb1 O4 2.527(3) . ?
Tb1 Tb1 3.9280(8) 3_766 ?
O10 N5 1.279(4) . ?
N2 C19 1.331(5) . ?
N2 C16 1.369(5) . ?
N2 H1A 0.839(19) . ?
O7 N4 1.284(4) . ?
O1 C1 1.357(5) . ?
O1 Tb1 2.372(3) 3_766 ?
O6 N4 1.266(4) . ?
C20 C19 1.490(6) . ?
C20 H10A 0.9800 . ?
C20 H10B 0.9800 . ?
C20 H10C 0.9800 . ?
O3 N3 1.273(5) . ?
O2 C11 1.319(5) . ?
C3 C4 1.353(7) . ?
C3 C2 1.413(6) . ?
C3 H13 0.9500 . ?
O8 N4 1.213(4) . ?
O4 N3 1.282(4) . ?
C2 C1 1.379(6) . ?
C2 H12 0.9500 . ?
O9 N5 1.275(4) . ?
C7 C8 1.369(7) . ?
C7 C5 1.415(6) . ?
C7 H17 0.9500 . ?
C8 C9 1.408(6) . ?
C8 H18 0.9500 . ?
O5 N3 1.210(5) . ?
O11 N5 1.217(4) . ?
C18 C17 1.361(7) . ?
C18 C19 1.413(6) . ?
C18 H8 0.9500 . ?
C16 C15 1.420(6) . ?
C16 C11 1.432(5) . ?
C1 C6 1.411(5) . ?
N1 C9 1.334(5) . ?
N1 C6 1.378(5) . ?
N1 H2A 0.860(19) . ?
C10 C9 1.486(6) . ?
C10 H20A 0.9800 . ?
C10 H20B 0.9800 . ?
C10 H20C 0.9800 . ?
C13 C14 1.365(6) . ?
C13 C12 1.404(6) . ?
C13 H3 0.9500 . ?
C17 C15 1.420(6) . ?
C17 H7 0.9500 . ?
C11 C12 1.384(6) . ?
C12 H2 0.9500 . ?
C15 C14 1.415(6) . ?
C6 C5 1.417(5) . ?
C4 C5 1.403(6) . ?
C4 H14 0.9500 . ?
C14 H4 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
O2 Tb1 O1 148.00(9) . . ?
O2 Tb1 O1 87.39(9) . 3_766 ?
O1 Tb1 O1 67.42(10) . 3_766 ?
O2 Tb1 O3 79.35(10) . . ?
O1 Tb1 O3 102.96(10) . . ?
O1 Tb1 O3 132.80(9) 3_766 . ?
O2 Tb1 O7 85.62(10) . . ?
O1 Tb1 O7 125.91(9) . . ?
O1 Tb1 O7 151.25(10) 3_766 . ?
O3 Tb1 O7 72.93(10) . . ?
O2 Tb1 O10 72.33(10) . . ?
O1 Tb1 O10 119.23(9) . . ?
O1 Tb1 O10 79.86(10) 3_766 . ?
O3 Tb1 O10 135.57(10) . . ?
O7 Tb1 O10 71.44(10) . . ?
O2 Tb1 O9 123.20(10) . . ?
O1 Tb1 O9 75.97(9) . . ?
O1 Tb1 O9 85.58(9) 3_766 . ?
O3 Tb1 O9 138.93(10) . . ?
O7 Tb1 O9 75.18(10) . . ?
O10 Tb1 O9 50.94(9) . . ?
O2 Tb1 O6 132.87(9) . . ?
O1 Tb1 O6 75.60(9) . . ?
O1 Tb1 O6 139.52(9) 3_766 . ?
O3 Tb1 O6 70.42(10) . . ?
O7 Tb1 O6 51.71(9) . . ?
O10 Tb1 O6 105.59(9) . . ?
O9 Tb1 O6 69.64(9) . . ?
O2 Tb1 O4 76.84(10) . . ?
O1 Tb1 O4 79.93(9) . . ?
O1 Tb1 O4 81.19(9) 3_766 . ?
O3 Tb1 O4 51.75(9) . . ?
O7 Tb1 O4 123.92(10) . . ?
O10 Tb1 O4 144.30(10) . . ?
O9 Tb1 O4 155.51(9) . . ?
O6 Tb1 O4 108.49(10) . . ?
O2 Tb1 Tb1 118.68(7) . 3_766 ?
O1 Tb1 Tb1 33.89(6) . 3_766 ?
O1 Tb1 Tb1 33.53(6) 3_766 3_766 ?
O3 Tb1 Tb1 122.99(7) . 3_766 ?
O7 Tb1 Tb1 151.68(7) . 3_766 ?
O10 Tb1 Tb1 100.71(7) . 3_766 ?
O9 Tb1 Tb1 78.95(6) . 3_766 ?
O6 Tb1 Tb1 108.09(6) . 3_766 ?
O4 Tb1 Tb1 78.64(7) . 3_766 ?
N5 O10 Tb1 97.7(2) . . ?
C19 N2 C16 124.5(4) . . ?
C19 N2 H1A 117(3) . . ?
C16 N2 H1A 118(3) . . ?
N4 O7 Tb1 97.7(2) . . ?
C1 O1 Tb1 124.8(2) . . ?
C1 O1 Tb1 122.2(2) . 3_766 ?
Tb1 O1 Tb1 112.58(10) . 3_766 ?
N4 O6 Tb1 94.3(2) . . ?
C19 C20 H10A 109.5 . . ?
C19 C20 H10B 109.5 . . ?
H10A C20 H10B 109.5 . . ?
C19 C20 H10C 109.5 . . ?
H10A C20 H10C 109.5 . . ?
H10B C20 H10C 109.5 . . ?
N3 O3 Tb1 97.4(2) . . ?
C11 O2 Tb1 162.8(3) . . ?
C4 C3 C2 121.6(4) . . ?
C4 C3 H13 119.2 . . ?
C2 C3 H13 119.2 . . ?
N3 O4 Tb1 93.0(2) . . ?
C1 C2 C3 120.5(4) . . ?
C1 C2 H12 119.8 . . ?
C3 C2 H12 119.8 . . ?
O8 N4 O6 122.4(3) . . ?
O8 N4 O7 121.4(3) . . ?
O6 N4 O7 116.2(3) . . ?
N5 O9 Tb1 96.5(2) . . ?
C8 C7 C5 121.0(4) . . ?
C8 C7 H17 119.5 . . ?
C5 C7 H17 119.5 . . ?
C7 C8 C9 121.2(4) . . ?
C7 C8 H18 119.4 . . ?
C9 C8 H18 119.4 . . ?
C17 C18 C19 120.7(4) . . ?
C17 C18 H8 119.6 . . ?
C19 C18 H8 119.6 . . ?
N2 C16 C15 118.8(4) . . ?
N2 C16 C11 118.4(4) . . ?
C15 C16 C11 122.8(4) . . ?
O1 C1 C2 123.5(4) . . ?
O1 C1 C6 118.6(3) . . ?
C2 C1 C6 117.9(4) . . ?
C9 N1 C6 124.3(4) . . ?
C9 N1 H2A 117(3) . . ?
C6 N1 H2A 118(3) . . ?
C9 C10 H20A 109.5 . . ?
C9 C10 H20B 109.5 . . ?
H20A C10 H20B 109.5 . . ?
C9 C10 H20C 109.5 . . ?
H20A C10 H20C 109.5 . . ?
H20B C10 H20C 109.5 . . ?
N2 C19 C18 117.8(4) . . ?
N2 C19 C20 118.2(4) . . ?
C18 C19 C20 124.0(4) . . ?
O11 N5 O9 122.7(4) . . ?
O11 N5 O10 122.6(4) . . ?
O9 N5 O10 114.7(3) . . ?
C14 C13 C12 122.4(4) . . ?
C14 C13 H3 118.8 . . ?
C12 C13 H3 118.8 . . ?
C18 C17 C15 120.8(4) . . ?
C18 C17 H7 119.6 . . ?
C15 C17 H7 119.6 . . ?
O2 C11 C12 126.1(4) . . ?
O2 C11 C16 117.5(4) . . ?
C12 C11 C16 116.4(4) . . ?
C11 C12 C13 121.2(4) . . ?
C11 C12 H2 119.4 . . ?
C13 C12 H2 119.4 . . ?
O5 N3 O3 121.7(4) . . ?
O5 N3 O4 122.1(4) . . ?
O3 N3 O4 116.2(3) . . ?
C14 C15 C16 117.6(4) . . ?
C14 C15 C17 125.1(4) . . ?
C16 C15 C17 117.3(4) . . ?
N1 C6 C1 119.4(4) . . ?
N1 C6 C5 119.3(4) . . ?
C1 C6 C5 121.3(4) . . ?
C3 C4 C5 119.9(4) . . ?
C3 C4 H14 120.0 . . ?
C5 C4 H14 120.0 . . ?
C4 C5 C7 124.7(4) . . ?
C4 C5 C6 118.6(4) . . ?
C7 C5 C6 116.7(4) . . ?
N1 C9 C8 117.4(4) . . ?
N1 C9 C10 118.5(4) . . ?
C8 C9 C10 124.1(4) . . ?
C13 C14 C15 119.6(4) . . ?
C13 C14 H4 120.2 . . ?
C15 C14 H4 120.2 . . ?

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
C4 C3 C2 C1 0.5(6) . . . . ?
Tb1 O6 N4 O8 176.3(4) . . . . ?
Tb1 O6 N4 O7 -2.8(3) . . . . ?
Tb1 O7 N4 O8 -176.2(3) . . . . ?
Tb1 O7 N4 O6 3.0(4) . . . . ?
C5 C7 C8 C9 -1.3(6) . . . . ?
C19 N2 C16 C15 0.9(6) . . . . ?
C19 N2 C16 C11 -178.1(4) . . . . ?
Tb1 O1 C1 C2 -81.2(4) . . . . ?
Tb1 O1 C1 C2 90.8(4) 3_766 . . . ?
Tb1 O1 C1 C6 98.5(4) . . . . ?
Tb1 O1 C1 C6 -89.5(4) 3_766 . . . ?
C3 C2 C1 O1 -177.4(4) . . . . ?
C3 C2 C1 C6 2.9(6) . . . . ?
C16 N2 C19 C18 0.8(6) . . . . ?
C16 N2 C19 C20 -179.5(4) . . . . ?
C17 C18 C19 N2 -1.0(6) . . . . ?
C17 C18 C19 C20 179.3(4) . . . . ?
Tb1 O9 N5 O11 174.7(3) . . . . ?
Tb1 O9 N5 O10 -4.1(3) . . . . ?
Tb1 O10 N5 O11 -174.6(3) . . . . ?
Tb1 O10 N5 O9 4.2(3) . . . . ?
C19 C18 C17 C15 -0.6(6) . . . . ?
Tb1 O2 C11 C12 -70.6(10) . . . . ?
Tb1 O2 C11 C16 109.8(9) . . . . ?
N2 C16 C11 O2 0.1(5) . . . . ?
C15 C16 C11 O2 -178.8(3) . . . . ?
N2 C16 C11 C12 -179.5(3) . . . . ?
C15 C16 C11 C12 1.6(6) . . . . ?
O2 C11 C12 C13 -179.8(4) . . . . ?
C16 C11 C12 C13 -0.3(6) . . . . ?
C14 C13 C12 C11 -0.5(6) . . . . ?
Tb1 O3 N3 O5 166.2(4) . . . . ?
Tb1 O3 N3 O4 -13.4(4) . . . . ?
Tb1 O4 N3 O5 -166.8(4) . . . . ?
Tb1 O4 N3 O3 12.8(3) . . . . ?
N2 C16 C15 C14 179.0(3) . . . . ?
C11 C16 C15 C14 -2.1(6) . . . . ?
N2 C16 C15 C17 -2.4(6) . . . . ?
C11 C16 C15 C17 176.5(4) . . . . ?
C18 C17 C15 C14 -179.2(4) . . . . ?
C18 C17 C15 C16 2.3(6) . . . . ?
C9 N1 C6 C1 177.7(4) . . . . ?
C9 N1 C6 C5 -1.9(6) . . . . ?
O1 C1 C6 N1 -4.2(5) . . . . ?
C2 C1 C6 N1 175.5(3) . . . . ?
O1 C1 C6 C5 175.4(3) . . . . ?
C2 C1 C6 C5 -4.9(6) . . . . ?
C2 C3 C4 C5 -2.1(6) . . . . ?
C3 C4 C5 C7 179.9(4) . . . . ?
C3 C4 C5 C6 0.2(6) . . . . ?
C8 C7 C5 C4 178.5(4) . . . . ?
C8 C7 C5 C6 -1.7(6) . . . . ?
N1 C6 C5 C4 -177.0(4) . . . . ?
C1 C6 C5 C4 3.4(6) . . . . ?
N1 C6 C5 C7 3.3(5) . . . . ?
C1 C6 C5 C7 -176.3(4) . . . . ?
C6 N1 C9 C8 -1.1(6) . . . . ?
C6 N1 C9 C10 179.9(4) . . . . ?
C7 C8 C9 N1 2.7(6) . . . . ?
C7 C8 C9 C10 -178.4(4) . . . . ?
C12 C13 C14 C15 0.0(6) . . . . ?
C16 C15 C14 C13 1.2(6) . . . . ?
C17 C15 C14 C13 -177.2(4) . . . . ?

_refine_diff_density_max         1.852
_refine_diff_density_min         -0.572
_refine_diff_density_rms         0.137

####################################################################### 
# 
# 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 1871950'
_audit_update_record             
;
2018-11-13 deposited with the CCDC.
2018-11-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H48 Cl6 N4 O6 Tb2'
_chemical_formula_weight         1259.40

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   10.835(5)
_cell_length_b                   12.142(6)
_cell_length_c                   18.646(9)
_cell_angle_alpha                90
_cell_angle_beta                 105.818(7)
_cell_angle_gamma                90
_cell_volume                     2360(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3722
_cell_measurement_theta_min      3.022
_cell_measurement_theta_max      27.501

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.772
_exptl_crystal_F_000             1240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    3.362
_shelx_estimated_absorpt_T_min   0.553
_shelx_estimated_absorpt_T_max   0.850
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5020
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   '(Higashi, 1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn 724+'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11123
_diffrn_reflns_av_unetI/netI     0.1964
_diffrn_reflns_av_R_equivalents  0.1026
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.053
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             5331
_reflns_number_gt                3110
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        
'CrystalClear (Rigaku Inc., 2008), SORTAV (Blessing, 1995)'
_computing_structure_solution    'SIR92 (Altomare et al, 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.0179P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5331
_refine_ls_number_parameters     224
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1379
_refine_ls_R_factor_gt           0.0787
_refine_ls_wR_factor_ref         0.2197
_refine_ls_wR_factor_gt          0.1682
_refine_ls_goodness_of_fit_ref   0.913
_refine_ls_restrained_S_all      0.913
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Tb1 Tb 0.01733(5) 0.87250(5) -0.05765(3) 0.0206(2) Uani 1 1 d . . . . .
Cl3 Cl 0.2232(3) 0.8240(3) 0.05462(16) 0.0307(7) Uani 1 1 d . . . . .
Cl2 Cl 0.1554(3) 0.8434(3) -0.15175(15) 0.0277(7) Uani 1 1 d . . . . .
Cl1 Cl -0.1962(3) 0.9153(3) -0.16230(16) 0.0374(8) Uani 1 1 d . . . . .
O2 O 0.0708(7) 1.0568(6) -0.0355(4) 0.0203(17) Uani 1 1 d . . . . .
N2 N 0.3246(9) 1.0982(8) 0.0165(5) 0.027(2) Uani 1 1 d . . . . .
H2A H 0.2826 1.0531 0.0383 0.033 Uiso 1 1 calc R U . . .
C17 C 0.4556(11) 1.2363(11) -0.0523(7) 0.0291(14) Uani 1 1 d . . . . .
H17 H 0.5041 1.2826 -0.0755 0.035 Uiso 1 1 calc R U . . .
C16 C 0.2573(10) 1.1468(9) -0.0492(6) 0.018(2) Uani 1 1 d . . . . .
C15 C 0.3190(11) 1.2179(11) -0.0870(6) 0.028(3) Uani 1 1 d . . . . .
C19 C 0.4489(11) 1.1144(10) 0.0494(6) 0.026(3) Uani 1 1 d . . . . .
C20 C 0.5030(11) 1.0570(12) 0.1206(7) 0.040(4) Uani 1 1 d . . . . .
H20A H 0.4701 1.0906 0.1594 0.060 Uiso 1 1 calc R U . . .
H20B H 0.5968 1.0629 0.1345 0.060 Uiso 1 1 calc R U . . .
H20C H 0.4782 0.9791 0.1151 0.060 Uiso 1 1 calc R U . . .
C12 C 0.0602(11) 1.1702(11) -0.1428(7) 0.0291(14) Uani 1 1 d . . . . .
H12 H -0.0282 1.1540 -0.1633 0.035 Uiso 1 1 calc R U . . .
C11 C 0.1244(9) 1.1230(9) -0.0760(6) 0.017(2) Uani 1 1 d . . . . .
C13 C 0.1209(14) 1.2409(11) -0.1813(7) 0.039(3) Uani 1 1 d . . . . .
H13 H 0.0732 1.2726 -0.2271 0.046 Uiso 1 1 calc R U . . .
C14 C 0.2484(11) 1.2652(10) -0.1540(7) 0.030(3) Uani 1 1 d . . . . .
H14 H 0.2888 1.3140 -0.1804 0.035 Uiso 1 1 calc R U . . .
C18 C 0.5110(11) 1.1874(11) 0.0121(7) 0.0291(14) Uani 1 1 d . . . . .
H18 H 0.5991 1.2027 0.0345 0.035 Uiso 1 1 calc R U . . .
O1 O -0.0605(7) 0.7160(7) -0.0376(4) 0.029(2) Uani 1 1 d . . . . .
C1 C -0.1198(16) 0.6378(11) -0.0130(9) 0.0466(15) Uani 1 1 d . . . . .
C2 C -0.2483(15) 0.6088(11) -0.0516(8) 0.0466(15) Uani 1 1 d . . . . .
H2 H -0.2899 0.6435 -0.0975 0.056 Uiso 1 1 calc R U . . .
C6 C -0.0595(16) 0.5831(13) 0.0526(8) 0.0466(15) Uani 1 1 d . . . . .
N1 N 0.0585(11) 0.6072(9) 0.0885(6) 0.035(3) Uani 1 1 d . . . . .
H1A H 0.0967 0.6584 0.0689 0.042 Uiso 1 1 calc R U . . .
C10 C 0.2618(14) 0.5957(11) 0.1872(8) 0.0466(15) Uani 1 1 d . . . . .
H10A H 0.2967 0.6347 0.1511 0.070 Uiso 1 1 calc R U . . .
H10B H 0.3132 0.5297 0.2047 0.070 Uiso 1 1 calc R U . . .
H10C H 0.2643 0.6441 0.2297 0.070 Uiso 1 1 calc R U . . .
C9 C 0.1253(11) 0.5628(11) 0.1506(7) 0.0291(14) Uani 1 1 d . . . . .
C3 C -0.3137(15) 0.5272(11) -0.0208(8) 0.0466(15) Uani 1 1 d . . . . .
H3 H -0.4016 0.5116 -0.0438 0.056 Uiso 1 1 calc R U . . .
C8 C 0.0651(15) 0.4784(12) 0.1814(8) 0.048(4) Uani 1 1 d . . . . .
H8 H 0.1110 0.4455 0.2271 0.058 Uiso 1 1 calc R U . . .
C5 C -0.1312(15) 0.4971(12) 0.0804(8) 0.0466(15) Uani 1 1 d . . . . .
C7 C -0.0547(15) 0.4431(12) 0.1483(8) 0.0466(15) Uani 1 1 d . . . . .
H7 H -0.0897 0.3832 0.1690 0.056 Uiso 1 1 calc R U . . .
C4 C -0.2505(15) 0.4723(12) 0.0411(8) 0.0466(15) Uani 1 1 d . . . . .
H4 H -0.2929 0.4130 0.0576 0.056 Uiso 1 1 calc R U . . .
O3 O 0.5763(14) 0.0191(13) 0.6969(7) 0.093(5) Uani 1 1 d . . . . .
H3A H 0.5036 0.0039 0.6687 0.140 Uiso 1 1 calc R U . . .
C21 C 0.588(2) 0.1371(16) 0.7068(14) 0.093(8) Uani 1 1 d . . . . .
H21A H 0.5650 0.1742 0.6577 0.112 Uiso 1 1 calc R U . . .
H21B H 0.6779 0.1566 0.7330 0.112 Uiso 1 1 calc R U . . .
C22 C 0.503(3) 0.1731(17) 0.7503(11) 0.114(9) Uani 1 1 d . . . . .
H22A H 0.4201 0.1944 0.7166 0.171 Uiso 1 1 calc R U . . .
H22B H 0.5410 0.2364 0.7810 0.171 Uiso 1 1 calc R U . . .
H22C H 0.4904 0.1128 0.7825 0.171 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
Tb1 O1 2.153(8) . ?
Tb1 O2 2.320(8) . ?
Tb1 O2 2.361(7) 3_575 ?
Tb1 Cl2 2.621(3) . ?
Tb1 Cl1 2.640(3) . ?
Tb1 Cl3 2.676(3) . ?
Tb1 Tb1 3.8458(18) 3_575 ?
O2 C11 1.338(12) . ?
O2 Tb1 2.361(7) 3_575 ?
N2 C19 1.334(14) . ?
N2 C16 1.376(13) . ?
N2 H2A 0.8800 . ?
C17 C18 1.327(16) . ?
C17 C15 1.462(15) . ?
C17 H17 0.9500 . ?
C16 C15 1.395(15) . ?
C16 C11 1.419(14) . ?
C15 C14 1.398(16) . ?
C19 C18 1.406(17) . ?
C19 C20 1.472(16) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C12 C11 1.375(15) . ?
C12 C13 1.395(16) . ?
C12 H12 0.9500 . ?
C13 C14 1.368(17) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C18 H18 0.9500 . ?
O1 C1 1.298(15) . ?
C1 C6 1.39(2) . ?
C1 C2 1.43(2) . ?
C2 C3 1.428(18) . ?
C2 H2 0.9500 . ?
C6 N1 1.306(18) . ?
C6 C5 1.48(2) . ?
N1 C9 1.303(15) . ?
N1 H1A 0.8800 . ?
C10 C9 1.504(18) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C9 C8 1.418(17) . ?
C3 C4 1.347(19) . ?
C3 H3 0.9500 . ?
C8 C7 1.35(2) . ?
C8 H8 0.9500 . ?
C5 C4 1.335(19) . ?
C5 C7 1.47(2) . ?
C7 H7 0.9500 . ?
C4 H4 0.9500 . ?
O3 C21 1.45(2) . ?
O3 H3A 0.8400 . ?
C21 C22 1.45(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
O1 Tb1 O2 155.7(3) . . ?
O1 Tb1 O2 86.4(3) . 3_575 ?
O2 Tb1 O2 69.5(3) . 3_575 ?
O1 Tb1 Cl2 108.6(2) . . ?
O2 Tb1 Cl2 95.09(18) . . ?
O2 Tb1 Cl2 163.9(2) 3_575 . ?
O1 Tb1 Cl1 89.8(2) . . ?
O2 Tb1 Cl1 93.9(2) . . ?
O2 Tb1 Cl1 91.35(19) 3_575 . ?
Cl2 Tb1 Cl1 94.40(10) . . ?
O1 Tb1 Cl3 87.3(2) . . ?
O2 Tb1 Cl3 87.64(19) . . ?
O2 Tb1 Cl3 85.57(19) 3_575 . ?
Cl2 Tb1 Cl3 89.30(10) . . ?
Cl1 Tb1 Cl3 175.85(9) . . ?
O1 Tb1 Tb1 120.7(2) . 3_575 ?
O2 Tb1 Tb1 35.10(17) . 3_575 ?
O2 Tb1 Tb1 34.42(18) 3_575 3_575 ?
Cl2 Tb1 Tb1 130.04(7) . 3_575 ?
Cl1 Tb1 Tb1 93.18(8) . 3_575 ?
Cl3 Tb1 Tb1 85.85(8) . 3_575 ?
C11 O2 Tb1 127.2(6) . . ?
C11 O2 Tb1 121.4(7) . 3_575 ?
Tb1 O2 Tb1 110.5(3) . 3_575 ?
C19 N2 C16 124.8(10) . . ?
C19 N2 H2A 117.6 . . ?
C16 N2 H2A 117.6 . . ?
C18 C17 C15 119.0(11) . . ?
C18 C17 H17 120.5 . . ?
C15 C17 H17 120.5 . . ?
N2 C16 C15 120.3(10) . . ?
N2 C16 C11 117.8(10) . . ?
C15 C16 C11 121.9(10) . . ?
C16 C15 C14 119.0(10) . . ?
C16 C15 C17 116.0(11) . . ?
C14 C15 C17 125.0(11) . . ?
N2 C19 C18 115.1(11) . . ?
N2 C19 C20 116.7(12) . . ?
C18 C19 C20 128.2(11) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C11 C12 C13 122.1(11) . . ?
C11 C12 H12 119.0 . . ?
C13 C12 H12 119.0 . . ?
O2 C11 C12 124.8(9) . . ?
O2 C11 C16 118.6(9) . . ?
C12 C11 C16 116.6(10) . . ?
C14 C13 C12 120.7(12) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 119.7(11) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C17 C18 C19 124.8(11) . . ?
C17 C18 H18 117.6 . . ?
C19 C18 H18 117.6 . . ?
C1 O1 Tb1 164.2(8) . . ?
O1 C1 C6 120.2(14) . . ?
O1 C1 C2 120.7(14) . . ?
C6 C1 C2 119.1(14) . . ?
C1 C2 C3 119.5(15) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
N1 C6 C1 120.3(14) . . ?
N1 C6 C5 120.9(15) . . ?
C1 C6 C5 118.8(15) . . ?
C9 N1 C6 126.3(12) . . ?
C9 N1 H1A 116.8 . . ?
C6 N1 H1A 116.8 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C9 C8 117.0(12) . . ?
N1 C9 C10 122.2(12) . . ?
C8 C9 C10 120.8(13) . . ?
C4 C3 C2 119.7(15) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C7 C8 C9 122.5(15) . . ?
C7 C8 H8 118.8 . . ?
C9 C8 H8 118.8 . . ?
C4 C5 C7 127.4(14) . . ?
C4 C5 C6 119.3(15) . . ?
C7 C5 C6 113.1(14) . . ?
C8 C7 C5 120.1(14) . . ?
C8 C7 H7 120.0 . . ?
C5 C7 H7 120.0 . . ?
C5 C4 C3 123.3(15) . . ?
C5 C4 H4 118.4 . . ?
C3 C4 H4 118.4 . . ?
C21 O3 H3A 109.5 . . ?
O3 C21 C22 108.8(17) . . ?
O3 C21 H21A 109.9 . . ?
C22 C21 H21A 109.9 . . ?
O3 C21 H21B 109.9 . . ?
C22 C21 H21B 109.9 . . ?
H21A C21 H21B 108.3 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
C19 N2 C16 C15 0.8(17) . . . . ?
C19 N2 C16 C11 -178.4(10) . . . . ?
N2 C16 C15 C14 179.4(11) . . . . ?
C11 C16 C15 C14 -1.4(17) . . . . ?
N2 C16 C15 C17 -0.3(16) . . . . ?
C11 C16 C15 C17 178.9(10) . . . . ?
C18 C17 C15 C16 -1.2(18) . . . . ?
C18 C17 C15 C14 179.1(12) . . . . ?
C16 N2 C19 C18 0.1(17) . . . . ?
C16 N2 C19 C20 178.6(10) . . . . ?
Tb1 O2 C11 C12 77.1(13) . . . . ?
Tb1 O2 C11 C12 -91.0(12) 3_575 . . . ?
Tb1 O2 C11 C16 -102.3(10) . . . . ?
Tb1 O2 C11 C16 89.5(10) 3_575 . . . ?
C13 C12 C11 O2 178.3(11) . . . . ?
C13 C12 C11 C16 -2.3(18) . . . . ?
N2 C16 C11 O2 1.3(15) . . . . ?
C15 C16 C11 O2 -177.9(10) . . . . ?
N2 C16 C11 C12 -178.2(10) . . . . ?
C15 C16 C11 C12 2.6(17) . . . . ?
C11 C12 C13 C14 0.7(19) . . . . ?
C12 C13 C14 C15 0.6(19) . . . . ?
C16 C15 C14 C13 -0.2(18) . . . . ?
C17 C15 C14 C13 179.4(11) . . . . ?
C15 C17 C18 C19 2(2) . . . . ?
N2 C19 C18 C17 -1.8(18) . . . . ?
C20 C19 C18 C17 180.0(13) . . . . ?
Tb1 O1 C1 C6 -85(4) . . . . ?
Tb1 O1 C1 C2 93(3) . . . . ?
O1 C1 C2 C3 -176.1(11) . . . . ?
C6 C1 C2 C3 2(2) . . . . ?
O1 C1 C6 N1 -2(2) . . . . ?
C2 C1 C6 N1 179.2(12) . . . . ?
O1 C1 C6 C5 177.9(11) . . . . ?
C2 C1 C6 C5 0(2) . . . . ?
C1 C6 N1 C9 179.4(12) . . . . ?
C5 C6 N1 C9 -1(2) . . . . ?
C6 N1 C9 C8 1(2) . . . . ?
C6 N1 C9 C10 179.3(12) . . . . ?
C1 C2 C3 C4 -5(2) . . . . ?
N1 C9 C8 C7 1(2) . . . . ?
C10 C9 C8 C7 -176.7(13) . . . . ?
N1 C6 C5 C4 -178.1(13) . . . . ?
C1 C6 C5 C4 2(2) . . . . ?
N1 C6 C5 C7 -1.9(19) . . . . ?
C1 C6 C5 C7 177.7(13) . . . . ?
C9 C8 C7 C5 -4(2) . . . . ?
C4 C5 C7 C8 180.0(13) . . . . ?
C6 C5 C7 C8 4.2(19) . . . . ?
C7 C5 C4 C3 179.6(13) . . . . ?
C6 C5 C4 C3 -5(2) . . . . ?
C2 C3 C4 C5 7(2) . . . . ?

_refine_diff_density_max         1.991
_refine_diff_density_min         -1.161
_refine_diff_density_rms         0.247

####################################################################### 
# 
# 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 1871952'
_audit_update_record             
;
2018-11-13 deposited with the CCDC.
2018-11-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H48 Cl6 N4 O6 Yb2'
_chemical_formula_weight         1287.64

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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   10.793(4)
_cell_length_b                   12.085(4)
_cell_length_c                   18.496(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.298(5)
_cell_angle_gamma                90
_cell_volume                     2327.0(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6011
_cell_measurement_theta_min      3.0254
_cell_measurement_theta_max      27.4739

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.838
_exptl_crystal_F_000             1260
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    4.390
_shelx_estimated_absorpt_T_min   0.668
_shelx_estimated_absorpt_T_max   0.810
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8238
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   '(Higashi, 1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn 724+'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8341
_diffrn_reflns_av_unetI/netI     0.1009
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.073
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             4527
_reflns_number_gt                3199
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        
'CrystalClear (Rigaku Inc., 2008), SORTAV (Blessing, 1995)'
_computing_structure_solution    'SIR92 (Altomare et al, 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0800P)²+0.0100P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4527
_refine_ls_number_parameters     206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0575
_refine_ls_wR_factor_ref         0.1602
_refine_ls_wR_factor_gt          0.1350
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1202(14) 0.6430(9) -0.0153(7) 0.0383(11) Uani 1 1 d . . . . .
C2 C -0.2475(15) 0.6110(9) -0.0528(7) 0.0383(11) Uani 1 1 d . . . . .
H2 H -0.2898 0.6485 -0.0977 0.046 Uiso 1 1 calc R U . . .
C3 C -0.3133(14) 0.5269(9) -0.0267(7) 0.0383(11) Uani 1 1 d . . . . .
H3 H -0.3986 0.5077 -0.0531 0.046 Uiso 1 1 calc R U . . .
C4 C -0.2535(14) 0.4744(9) 0.0360(7) 0.0383(11) Uani 1 1 d . . . . .
H4 H -0.2974 0.4155 0.0527 0.046 Uiso 1 1 calc R U . . .
C5 C -0.1282(15) 0.5012(9) 0.0793(7) 0.0383(11) Uani 1 1 d . . . . .
C6 C -0.0631(15) 0.5826(10) 0.0527(7) 0.0383(11) Uani 1 1 d . . . . .
C7 C -0.0564(14) 0.4461(10) 0.1451(7) 0.0383(11) Uani 1 1 d . . . . .
H7 H -0.0925 0.3838 0.1633 0.046 Uiso 1 1 calc R U . . .
C8 C 0.0647(14) 0.4817(9) 0.1827(7) 0.0383(11) Uani 1 1 d . . . . .
H8 H 0.1052 0.4505 0.2301 0.046 Uiso 1 1 calc R U . . .
C9 C 0.1289(14) 0.5618(9) 0.1532(7) 0.0383(11) Uani 1 1 d . . . . .
C10 C 0.2614(14) 0.6000(11) 0.1894(7) 0.045(4) Uani 1 1 d . . . . .
H10A H 0.2834 0.6615 0.1605 0.068 Uiso 1 1 calc R U . . .
H10B H 0.3218 0.5389 0.1911 0.068 Uiso 1 1 calc R U . . .
H10C H 0.2665 0.6250 0.2405 0.068 Uiso 1 1 calc R U . . .
C11 C 0.1239(10) 1.1239(8) -0.0779(5) 0.015(2) Uani 1 1 d . . . . .
C12 C 0.0560(10) 1.1655(10) -0.1470(6) 0.026(3) Uani 1 1 d . . . . .
H12 H -0.0313 1.1463 -0.1683 0.032 Uiso 1 1 calc R U . . .
C13 C 0.1203(11) 1.2361(8) -0.1835(6) 0.0220(11) Uani 1 1 d . . . . .
H13 H 0.0742 1.2666 -0.2302 0.026 Uiso 1 1 calc R U . . .
C14 C 0.2493(11) 1.2649(8) -0.1554(6) 0.0220(11) Uani 1 1 d . . . . .
H14 H 0.2891 1.3149 -0.1819 0.026 Uiso 1 1 calc R U . . .
C15 C 0.3205(11) 1.2180(8) -0.0859(6) 0.0220(11) Uani 1 1 d . . . . .
C16 C 0.2552(11) 1.1478(8) -0.0510(6) 0.0220(11) Uani 1 1 d . . . . .
C17 C 0.4520(11) 1.2370(9) -0.0532(6) 0.0220(11) Uani 1 1 d . . . . .
H17 H 0.4979 1.2863 -0.0767 0.026 Uiso 1 1 calc R U . . .
C18 C 0.5131(10) 1.1864(8) 0.0107(6) 0.024(2) Uani 1 1 d . . . . .
H18 H 0.6024 1.1985 0.0317 0.029 Uiso 1 1 calc R U . . .
C19 C 0.4446(11) 1.1148(8) 0.0469(6) 0.021(2) Uani 1 1 d . . . . .
C20 C 0.5077(11) 1.0564(9) 0.1222(6) 0.027(3) Uani 1 1 d . . . . .
H20A H 0.4574 1.0716 0.1581 0.041 Uiso 1 1 calc R U . . .
H20B H 0.5954 1.0842 0.1421 0.041 Uiso 1 1 calc R U . . .
H20C H 0.5102 0.9764 0.1139 0.041 Uiso 1 1 calc R U . . .
C21 C 0.408(2) 0.6343(13) 0.7903(15) 0.121(11) Uani 1 1 d . . . . .
H21A H 0.4286 0.6708 0.8399 0.145 Uiso 1 1 calc R U . . .
H21B H 0.3184 0.6529 0.7640 0.145 Uiso 1 1 calc R U . . .
C22 C 0.491(2) 0.6787(13) 0.7482(8) 0.088(7) Uani 1 1 d . . . . .
H22A H 0.5806 0.6737 0.7781 0.132 Uiso 1 1 calc R U . . .
H22B H 0.4689 0.7563 0.7359 0.132 Uiso 1 1 calc R U . . .
H22C H 0.4805 0.6362 0.7018 0.132 Uiso 1 1 calc R U . . .
Cl1 Cl -0.1894(3) 0.9164(2) -0.15942(14) 0.0287(6) Uani 1 1 d . . . . .
Cl2 Cl 0.1536(3) 0.8443(2) -0.14830(14) 0.0231(6) Uani 1 1 d . . . . .
Cl3 Cl 0.2220(3) 0.8272(2) 0.05449(14) 0.0242(6) Uani 1 1 d . . . . .
N1 N 0.0596(12) 0.6107(7) 0.0880(6) 0.0383(11) Uani 1 1 d . . . . .
H1A H 0.0967 0.6631 0.0681 0.046 Uiso 1 1 calc R U . . .
N2 N 0.3214(8) 1.0970(6) 0.0151(4) 0.0136(17) Uani 1 1 d . . . . .
H2A H 0.2795 1.0509 0.0370 0.016 Uiso 1 1 calc R U . . .
O1 O -0.0538(7) 0.7204(6) -0.0386(4) 0.0262(18) Uani 1 1 d . . . . .
O2 O 0.0692(6) 1.0542(5) -0.0359(3) 0.0142(14) Uani 1 1 d . . . . .
O3 O 0.4178(12) 0.5205(10) 0.8009(6) 0.073(4) Uani 1 1 d . . . . .
H3A H 0.4759 0.5064 0.8399 0.110 Uiso 1 1 calc R U . . .
Yb1 Yb 0.01795(4) 0.87511(3) -0.05551(2) 0.01483(17) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.318(13) . ?
C1 C2 1.420(19) . ?
C1 C6 1.444(18) . ?
C2 C3 1.397(16) . ?
C2 H2 0.9500 . ?
C3 C4 1.331(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.416(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.374(16) . ?
C5 C7 1.423(18) . ?
C6 N1 1.356(18) . ?
C7 C8 1.378(19) . ?
C7 H7 0.9500 . ?
C8 C9 1.383(16) . ?
C8 H8 0.9500 . ?
C9 N1 1.374(17) . ?
C9 C10 1.484(19) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O2 1.380(11) . ?
C11 C12 1.388(14) . ?
C11 C16 1.403(15) . ?
C12 C13 1.383(14) . ?
C12 H12 0.9500 . ?
C13 C14 1.396(15) . ?
C13 H13 0.9500 . ?
C14 C15 1.430(15) . ?
C14 H14 0.9500 . ?
C15 C16 1.368(14) . ?
C15 C17 1.407(15) . ?
C16 N2 1.387(13) . ?
C17 C18 1.339(15) . ?
C17 H17 0.9500 . ?
C18 C19 1.416(14) . ?
C18 H18 0.9500 . ?
C19 N2 1.322(13) . ?
C19 C20 1.549(13) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 O3 1.389(18) . ?
C21 C22 1.44(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
Cl1 Yb1 2.585(3) . ?
Cl2 Yb1 2.560(2) . ?
Cl3 Yb1 2.638(3) . ?
N1 H1A 0.8800 . ?
N2 H2A 0.8800 . ?
O1 Yb1 2.079(7) . ?
O2 Yb1 2.239(6) . ?
O2 Yb1 2.305(6) 3_575 ?
O3 H3A 0.8400 . ?
Yb1 O2 2.305(6) 3_575 ?
Yb1 Yb1 3.7281(12) 3_575 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 124.9(12) . . ?
O1 C1 C6 120.0(13) . . ?
C2 C1 C6 115.1(11) . . ?
C3 C2 C1 123.0(13) . . ?
C3 C2 H2 118.5 . . ?
C1 C2 H2 118.5 . . ?
C4 C3 C2 118.3(14) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C3 C4 C5 123.7(12) . . ?
C3 C4 H4 118.1 . . ?
C5 C4 H4 118.1 . . ?
C6 C5 C4 117.6(12) . . ?
C6 C5 C7 115.3(14) . . ?
C4 C5 C7 126.8(11) . . ?
N1 C6 C5 122.2(13) . . ?
N1 C6 C1 115.5(10) . . ?
C5 C6 C1 122.2(14) . . ?
C8 C7 C5 121.0(11) . . ?
C8 C7 H7 119.5 . . ?
C5 C7 H7 119.5 . . ?
C7 C8 C9 121.8(13) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
N1 C9 C8 115.7(13) . . ?
N1 C9 C10 119.9(10) . . ?
C8 C9 C10 124.3(13) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 C12 122.6(9) . . ?
O2 C11 C16 117.9(8) . . ?
C12 C11 C16 119.4(9) . . ?
C13 C12 C11 117.5(10) . . ?
C13 C12 H12 121.3 . . ?
C11 C12 H12 121.3 . . ?
C12 C13 C14 123.5(10) . . ?
C12 C13 H13 118.2 . . ?
C14 C13 H13 118.2 . . ?
C13 C14 C15 118.8(10) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C16 C15 C17 119.1(10) . . ?
C16 C15 C14 116.6(10) . . ?
C17 C15 C14 124.3(9) . . ?
C15 C16 N2 118.7(10) . . ?
C15 C16 C11 124.0(10) . . ?
N2 C16 C11 117.3(9) . . ?
C18 C17 C15 120.7(10) . . ?
C18 C17 H17 119.7 . . ?
C15 C17 H17 119.7 . . ?
C17 C18 C19 120.0(10) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
N2 C19 C18 118.6(9) . . ?
N2 C19 C20 118.5(9) . . ?
C18 C19 C20 122.9(10) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O3 C21 C22 114.4(14) . . ?
O3 C21 H21A 108.7 . . ?
C22 C21 H21A 108.7 . . ?
O3 C21 H21B 108.7 . . ?
C22 C21 H21B 108.7 . . ?
H21A C21 H21B 107.6 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C6 N1 C9 123.5(10) . . ?
C6 N1 H1A 118.3 . . ?
C9 N1 H1A 118.3 . . ?
C19 N2 C16 122.9(8) . . ?
C19 N2 H2A 118.5 . . ?
C16 N2 H2A 118.5 . . ?
C1 O1 Yb1 160.6(7) . . ?
C11 O2 Yb1 128.5(5) . . ?
C11 O2 Yb1 120.3(5) . 3_575 ?
Yb1 O2 Yb1 110.2(3) . 3_575 ?
C21 O3 H3A 109.5 . . ?
O1 Yb1 O2 158.6(2) . . ?
O1 Yb1 O2 89.0(2) . 3_575 ?
O2 Yb1 O2 69.8(3) . 3_575 ?
O1 Yb1 Cl2 105.7(2) . . ?
O2 Yb1 Cl2 95.09(17) . . ?
O2 Yb1 Cl2 164.15(17) 3_575 . ?
O1 Yb1 Cl1 90.1(2) . . ?
O2 Yb1 Cl1 93.57(18) . . ?
O2 Yb1 Cl1 91.87(18) 3_575 . ?
Cl2 Yb1 Cl1 93.77(9) . . ?
O1 Yb1 Cl3 87.4(2) . . ?
O2 Yb1 Cl3 88.09(18) . . ?
O2 Yb1 Cl3 86.27(17) 3_575 . ?
Cl2 Yb1 Cl3 88.66(9) . . ?
Cl1 Yb1 Cl3 176.93(8) . . ?
O1 Yb1 Yb1 123.29(19) . 3_575 ?
O2 Yb1 Yb1 35.46(16) . 3_575 ?
O2 Yb1 Yb1 34.30(16) 3_575 3_575 ?
Cl2 Yb1 Yb1 130.40(6) . 3_575 ?
Cl1 Yb1 Yb1 93.30(7) . 3_575 ?
Cl3 Yb1 Yb1 86.54(6) . 3_575 ?

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 C1 C2 C3 178.7(10) . . . . ?
C6 C1 C2 C3 -0.4(17) . . . . ?
C1 C2 C3 C4 -0.2(17) . . . . ?
C2 C3 C4 C5 2.2(18) . . . . ?
C3 C4 C5 C6 -3.3(18) . . . . ?
C3 C4 C5 C7 -177.3(11) . . . . ?
C4 C5 C6 N1 -176.7(11) . . . . ?
C7 C5 C6 N1 -2.1(17) . . . . ?
C4 C5 C6 C1 2.5(17) . . . . ?
C7 C5 C6 C1 177.2(10) . . . . ?
O1 C1 C6 N1 -0.7(16) . . . . ?
C2 C1 C6 N1 178.5(10) . . . . ?
O1 C1 C6 C5 -180.0(10) . . . . ?
C2 C1 C6 C5 -0.8(17) . . . . ?
C6 C5 C7 C8 6.8(16) . . . . ?
C4 C5 C7 C8 -179.1(11) . . . . ?
C5 C7 C8 C9 -9.1(18) . . . . ?
C7 C8 C9 N1 6.1(17) . . . . ?
C7 C8 C9 C10 -177.3(11) . . . . ?
O2 C11 C12 C13 179.0(9) . . . . ?
C16 C11 C12 C13 -4.7(15) . . . . ?
C11 C12 C13 C14 1.5(16) . . . . ?
C12 C13 C14 C15 1.2(15) . . . . ?
C13 C14 C15 C16 -0.7(14) . . . . ?
C13 C14 C15 C17 177.4(9) . . . . ?
C17 C15 C16 N2 -0.5(14) . . . . ?
C14 C15 C16 N2 177.7(8) . . . . ?
C17 C15 C16 C11 179.1(9) . . . . ?
C14 C15 C16 C11 -2.7(14) . . . . ?
O2 C11 C16 C15 -178.0(9) . . . . ?
C12 C11 C16 C15 5.6(15) . . . . ?
O2 C11 C16 N2 1.6(13) . . . . ?
C12 C11 C16 N2 -174.8(9) . . . . ?
C16 C15 C17 C18 0.7(15) . . . . ?
C14 C15 C17 C18 -177.3(9) . . . . ?
C15 C17 C18 C19 -1.4(15) . . . . ?
C17 C18 C19 N2 2.0(14) . . . . ?
C17 C18 C19 C20 -178.0(9) . . . . ?
C5 C6 N1 C9 -0.6(18) . . . . ?
C1 C6 N1 C9 -179.9(10) . . . . ?
C8 C9 N1 C6 -1.3(16) . . . . ?
C10 C9 N1 C6 -178.1(10) . . . . ?
C18 C19 N2 C16 -1.9(14) . . . . ?
C20 C19 N2 C16 178.1(8) . . . . ?
C15 C16 N2 C19 1.2(14) . . . . ?
C11 C16 N2 C19 -178.5(9) . . . . ?
C2 C1 O1 Yb1 86(3) . . . . ?
C6 C1 O1 Yb1 -95(3) . . . . ?
C12 C11 O2 Yb1 73.9(11) . . . . ?
C16 C11 O2 Yb1 -102.4(9) . . . . ?
C12 C11 O2 Yb1 -93.9(10) . . . 3_575 ?
C16 C11 O2 Yb1 89.8(9) . . . 3_575 ?

_refine_diff_density_max         1.600
_refine_diff_density_min         -1.237
_refine_diff_density_rms         0.236

####################################################################### 
# 
# 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 1871953'
_audit_update_record             
;
2018-11-13 deposited with the CCDC.
2018-11-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H36 N10 O22 Y2'
_chemical_formula_weight         1186.61

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'
Y Y -2.7962 3.5667 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.614(5)
_cell_length_b                   18.172(8)
_cell_length_c                   12.413(6)
_cell_angle_alpha                90
_cell_angle_beta                 110.223(5)
_cell_angle_gamma                90
_cell_volume                     2246.6(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5468
_cell_measurement_theta_min      3.0348
_cell_measurement_theta_max      27.4662

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.754
_exptl_crystal_F_000             1200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.670
_shelx_estimated_absorpt_T_min   0.690
_shelx_estimated_absorpt_T_max   0.776
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7113
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   '(Higashi, 1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn 724+'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9088
_diffrn_reflns_av_unetI/netI     0.1596
_diffrn_reflns_av_R_equivalents  0.0723
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.011
_diffrn_reflns_theta_max         27.490
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5086
_reflns_number_gt                3096
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        
'CrystalClear (Rigaku Inc., 2008), SORTAV (Blessing, 1995)'
_computing_structure_solution    'SIR92 (Altomare et al, 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0300P)²+0.1000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5086
_refine_ls_number_parameters     344
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1318
_refine_ls_R_factor_gt           0.0668
_refine_ls_wR_factor_ref         0.1179
_refine_ls_wR_factor_gt          0.1002
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Y1 Y 1.11751(4) 0.97757(3) 0.15518(4) 0.01560(13) Uani 1 1 d . . . . .
O1 O 0.8979(3) 0.97597(19) 0.0243(2) 0.0146(7) Uani 1 1 d . . . . .
O4 O 1.1279(3) 0.8615(2) 0.0508(3) 0.0268(9) Uani 1 1 d . . . . .
O3 O 1.3022(3) 0.8922(2) 0.1950(3) 0.0247(9) Uani 1 1 d . . . . .
N2 N 0.8787(4) 0.9225(2) 0.3592(3) 0.0180(9) Uani 1 1 d . . . . .
O2 O 1.0553(3) 0.89254(18) 0.2527(3) 0.0198(8) Uani 1 1 d . . . . .
N1 N 0.8177(4) 0.8312(3) 0.0047(3) 0.0212(10) Uani 1 1 d D . . . .
O5 O 1.2880(4) 0.7810(2) 0.1274(3) 0.0458(12) Uani 1 1 d . . . . .
C1 C 0.7914(4) 0.9567(3) 0.0547(4) 0.0184(11) Uani 1 1 d . . . . .
C6 C 0.7530(4) 0.8824(3) 0.0481(4) 0.0176(11) Uani 1 1 d . . . . .
C18 C 0.7157(4) 0.8903(3) 0.4391(4) 0.0231(12) Uani 1 1 d . . . . .
H18 H 0.6519 0.9041 0.4734 0.028 Uiso 1 1 calc R U . . .
C20 C 0.7804(5) 1.0245(3) 0.4285(4) 0.0253(12) Uani 1 1 d . . . . .
H20A H 0.8314 1.0524 0.3898 0.038 Uiso 1 1 calc R U . . .
H20B H 0.8165 1.0346 0.5111 0.038 Uiso 1 1 calc R U . . .
H20C H 0.6858 1.0391 0.3977 0.038 Uiso 1 1 calc R U . . .
C10 C 0.8697(5) 0.7109(3) -0.0534(4) 0.0298(13) Uani 1 1 d . . . . .
H10A H 0.9051 0.7407 -0.1023 0.045 Uiso 1 1 calc R U . . .
H10B H 0.8115 0.6722 -0.0996 0.045 Uiso 1 1 calc R U . . .
H10C H 0.9443 0.6884 0.0081 0.045 Uiso 1 1 calc R U . . .
N3 N 1.2402(4) 0.8426(3) 0.1240(4) 0.0288(11) Uani 1 1 d . . . . .
C16 C 0.9010(4) 0.8511(3) 0.3385(4) 0.0189(11) Uani 1 1 d . . . . .
C19 C 0.7921(5) 0.9443(3) 0.4084(4) 0.0246(12) Uani 1 1 d . . . . .
C3 C 0.6109(4) 0.9839(3) 0.1280(4) 0.0253(13) Uani 1 1 d . . . . .
H3 H 0.5605 1.0193 0.1524 0.030 Uiso 1 1 calc R U . . .
C2 C 0.7184(4) 1.0072(3) 0.0922(4) 0.0187(11) Uani 1 1 d . . . . .
H2 H 0.7400 1.0580 0.0942 0.022 Uiso 1 1 calc R U . . .
C14 C 0.8548(5) 0.7212(3) 0.3476(4) 0.0242(12) Uani 1 1 d . . . . .
H14 H 0.8093 0.6819 0.3690 0.029 Uiso 1 1 calc R U . . .
C15 C 0.8285(4) 0.7950(3) 0.3702(4) 0.0214(12) Uani 1 1 d . . . . .
C9 C 0.7909(5) 0.7587(3) -0.0024(4) 0.0239(12) Uani 1 1 d . . . . .
C17 C 0.7340(5) 0.8177(3) 0.4192(4) 0.0244(12) Uani 1 1 d . . . . .
H17 H 0.6811 0.7816 0.4392 0.029 Uiso 1 1 calc R U . . .
C7 C 0.6232(5) 0.7816(3) 0.0834(4) 0.0282(13) Uani 1 1 d . . . . .
H7 H 0.5557 0.7635 0.1107 0.034 Uiso 1 1 calc R U . . .
C11 C 0.9960(4) 0.8365(3) 0.2816(4) 0.0207(12) Uani 1 1 d . . . . .
C5 C 0.6499(4) 0.8582(3) 0.0868(4) 0.0204(12) Uani 1 1 d . . . . .
C8 C 0.6935(5) 0.7337(3) 0.0414(4) 0.0299(14) Uani 1 1 d . . . . .
H8 H 0.6762 0.6824 0.0419 0.036 Uiso 1 1 calc R U . . .
C12 C 1.0160(4) 0.7629(3) 0.2625(4) 0.0200(11) Uani 1 1 d . . . . .
H12 H 1.0789 0.7502 0.2266 0.024 Uiso 1 1 calc R U . . .
C13 C 0.9457(5) 0.7067(3) 0.2949(4) 0.0255(12) Uani 1 1 d . . . . .
H13 H 0.9618 0.6570 0.2797 0.031 Uiso 1 1 calc R U . . .
C4 C 0.5797(5) 0.9104(3) 0.1276(4) 0.0282(14) Uani 1 1 d . . . . .
H4 H 0.5106 0.8949 0.1548 0.034 Uiso 1 1 calc R U . . .
O10 O 0.9994(3) 1.0402(2) 0.2687(3) 0.0224(8) Uani 1 1 d . . . . .
O9 O 1.0841(3) 1.11223(19) 0.1732(3) 0.0215(8) Uani 1 1 d . . . . .
O7 O 1.2794(3) 1.0116(2) 0.3385(3) 0.0240(8) Uani 1 1 d . . . . .
O6 O 1.3323(3) 1.04608(19) 0.1921(3) 0.0218(8) Uani 1 1 d . . . . .
O11 O 0.9623(3) 1.1591(2) 0.2667(3) 0.0365(10) Uani 1 1 d . . . . .
N5 N 1.0139(4) 1.1062(2) 0.2381(3) 0.0229(10) Uani 1 1 d . . . . .
N4 N 1.3615(4) 1.0453(2) 0.3007(3) 0.0237(10) Uani 1 1 d . . . . .
O8 O 1.4612(3) 1.0767(2) 0.3651(3) 0.0325(10) Uani 1 1 d . . . . .
H1A H 0.917(4) 0.960(3) 0.337(4) 0.019(15) Uiso 1 1 d . . . . .
H2A H 0.872(4) 0.844(3) -0.026(4) 0.05(2) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Y1 O2 2.200(3) . ?
Y1 O1 2.335(3) 3_775 ?
Y1 O1 2.336(3) . ?
Y1 O7 2.411(3) . ?
Y1 O3 2.413(3) . ?
Y1 O10 2.465(3) . ?
Y1 O9 2.494(4) . ?
Y1 O6 2.497(3) . ?
Y1 O4 2.498(4) . ?
Y1 Y1 3.8840(17) 3_775 ?
O1 C1 1.355(5) . ?
O1 Y1 2.335(3) 3_775 ?
O4 N3 1.271(5) . ?
O3 N3 1.272(5) . ?
N2 C19 1.328(6) . ?
N2 C16 1.359(6) . ?
N2 H1A 0.88(5) . ?
O2 C11 1.310(6) . ?
N1 C9 1.344(6) . ?
N1 C6 1.372(6) . ?
N1 H2A 0.83(2) . ?
O5 N3 1.225(5) . ?
C1 C2 1.381(6) . ?
C1 C6 1.406(7) . ?
C6 C5 1.408(6) . ?
C18 C17 1.369(7) . ?
C18 C19 1.407(7) . ?
C18 H18 0.9500 . ?
C20 C19 1.489(7) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C10 C9 1.489(7) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C16 C15 1.413(7) . ?
C16 C11 1.442(6) . ?
C3 C4 1.376(7) . ?
C3 C2 1.424(6) . ?
C3 H3 0.9500 . ?
C2 H2 0.9500 . ?
C14 C13 1.366(7) . ?
C14 C15 1.417(7) . ?
C14 H14 0.9500 . ?
C15 C17 1.403(7) . ?
C9 C8 1.400(7) . ?
C17 H17 0.9500 . ?
C7 C8 1.362(7) . ?
C7 C5 1.418(7) . ?
C7 H7 0.9500 . ?
C11 C12 1.387(7) . ?
C5 C4 1.405(7) . ?
C8 H8 0.9500 . ?
C12 C13 1.403(7) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C4 H4 0.9500 . ?
O10 N5 1.282(5) . ?
O9 N5 1.277(5) . ?
O7 N4 1.279(5) . ?
O6 N4 1.275(5) . ?
O11 N5 1.219(5) . ?
N4 O8 1.225(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Y1 O1 147.50(11) . 3_775 ?
O2 Y1 O1 87.51(11) . . ?
O1 Y1 O1 67.47(12) 3_775 . ?
O2 Y1 O7 84.97(12) . . ?
O1 Y1 O7 126.88(11) 3_775 . ?
O1 Y1 O7 150.96(11) . . ?
O2 Y1 O3 79.20(12) . . ?
O1 Y1 O3 102.25(11) 3_775 . ?
O1 Y1 O3 132.77(12) . . ?
O7 Y1 O3 73.02(12) . . ?
O2 Y1 O10 72.62(12) . . ?
O1 Y1 O10 119.78(12) 3_775 . ?
O1 Y1 O10 79.68(11) . . ?
O7 Y1 O10 71.30(11) . . ?
O3 Y1 O10 135.85(12) . . ?
O2 Y1 O9 124.09(12) . . ?
O1 Y1 O9 76.45(11) 3_775 . ?
O1 Y1 O9 86.32(11) . . ?
O7 Y1 O9 74.98(11) . . ?
O3 Y1 O9 138.02(11) . . ?
O10 Y1 O9 51.60(11) . . ?
O2 Y1 O6 132.68(11) . . ?
O1 Y1 O6 75.71(10) 3_775 . ?
O1 Y1 O6 139.65(11) . . ?
O7 Y1 O6 52.51(11) . . ?
O3 Y1 O6 69.99(12) . . ?
O10 Y1 O6 106.10(11) . . ?
O9 Y1 O6 69.13(11) . . ?
O2 Y1 O4 76.58(12) . . ?
O1 Y1 O4 79.13(12) 3_775 . ?
O1 Y1 O4 80.86(11) . . ?
O7 Y1 O4 124.14(11) . . ?
O3 Y1 O4 52.03(11) . . ?
O10 Y1 O4 144.01(12) . . ?
O9 Y1 O4 155.29(11) . . ?
O6 Y1 O4 108.35(11) . . ?
O2 Y1 Y1 118.75(8) . 3_775 ?
O1 Y1 Y1 33.74(7) 3_775 3_775 ?
O1 Y1 Y1 33.73(7) . 3_775 ?
O7 Y1 Y1 152.44(9) . 3_775 ?
O3 Y1 Y1 122.41(8) . 3_775 ?
O10 Y1 Y1 101.00(8) . 3_775 ?
O9 Y1 Y1 79.66(7) . 3_775 ?
O6 Y1 Y1 108.05(8) . 3_775 ?
O4 Y1 Y1 77.95(8) . 3_775 ?
C1 O1 Y1 124.7(2) . 3_775 ?
C1 O1 Y1 122.5(2) . . ?
Y1 O1 Y1 112.53(12) 3_775 . ?
N3 O4 Y1 93.2(3) . . ?
N3 O3 Y1 97.2(3) . . ?
C19 N2 C16 124.4(5) . . ?
C19 N2 H1A 113(3) . . ?
C16 N2 H1A 123(3) . . ?
C11 O2 Y1 163.8(3) . . ?
C9 N1 C6 124.6(5) . . ?
C9 N1 H2A 114(4) . . ?
C6 N1 H2A 121(4) . . ?
O1 C1 C2 122.8(4) . . ?
O1 C1 C6 119.0(4) . . ?
C2 C1 C6 118.1(4) . . ?
N1 C6 C1 120.0(4) . . ?
N1 C6 C5 118.3(5) . . ?
C1 C6 C5 121.6(5) . . ?
C17 C18 C19 119.5(5) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O5 N3 O4 123.1(4) . . ?
O5 N3 O3 121.0(4) . . ?
O4 N3 O3 115.9(4) . . ?
N2 C16 C15 119.3(4) . . ?
N2 C16 C11 117.7(4) . . ?
C15 C16 C11 122.9(5) . . ?
N2 C19 C18 118.1(5) . . ?
N2 C19 C20 118.6(5) . . ?
C18 C19 C20 123.2(5) . . ?
C4 C3 C2 120.3(5) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C1 C2 C3 120.8(5) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C13 C14 C15 119.8(5) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C17 C15 C16 116.6(5) . . ?
C17 C15 C14 125.7(5) . . ?
C16 C15 C14 117.7(5) . . ?
N1 C9 C8 117.4(5) . . ?
N1 C9 C10 117.5(5) . . ?
C8 C9 C10 125.1(5) . . ?
C18 C17 C15 121.9(5) . . ?
C18 C17 H17 119.0 . . ?
C15 C17 H17 119.0 . . ?
C8 C7 C5 120.5(5) . . ?
C8 C7 H7 119.7 . . ?
C5 C7 H7 119.7 . . ?
O2 C11 C12 125.9(5) . . ?
O2 C11 C16 118.3(5) . . ?
C12 C11 C16 115.8(5) . . ?
C4 C5 C6 118.9(5) . . ?
C4 C5 C7 123.2(5) . . ?
C6 C5 C7 117.9(5) . . ?
C7 C8 C9 121.1(5) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C11 C12 C13 121.7(5) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C14 C13 C12 122.0(5) . . ?
C14 C13 H13 119.0 . . ?
C12 C13 H13 119.0 . . ?
C3 C4 C5 120.0(5) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
N5 O10 Y1 97.2(3) . . ?
N5 O9 Y1 96.0(3) . . ?
N4 O7 Y1 97.5(2) . . ?
N4 O6 Y1 93.5(2) . . ?
O11 N5 O9 122.3(5) . . ?
O11 N5 O10 122.6(4) . . ?
O9 N5 O10 115.0(4) . . ?
O8 N4 O6 121.6(4) . . ?
O8 N4 O7 121.9(4) . . ?
O6 N4 O7 116.5(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Y1 O1 C1 C2 -82.6(5) 3_775 . . . ?
Y1 O1 C1 C2 90.6(4) . . . . ?
Y1 O1 C1 C6 97.4(4) 3_775 . . . ?
Y1 O1 C1 C6 -89.4(4) . . . . ?
C9 N1 C6 C1 178.2(4) . . . . ?
C9 N1 C6 C5 -0.9(6) . . . . ?
O1 C1 C6 N1 -4.0(6) . . . . ?
C2 C1 C6 N1 176.0(4) . . . . ?
O1 C1 C6 C5 175.0(4) . . . . ?
C2 C1 C6 C5 -5.0(6) . . . . ?
Y1 O4 N3 O5 167.4(5) . . . . ?
Y1 O4 N3 O3 -12.7(4) . . . . ?
Y1 O3 N3 O5 -166.9(4) . . . . ?
Y1 O3 N3 O4 13.2(4) . . . . ?
C19 N2 C16 C15 0.1(7) . . . . ?
C19 N2 C16 C11 178.4(4) . . . . ?
C16 N2 C19 C18 -1.5(7) . . . . ?
C16 N2 C19 C20 178.5(4) . . . . ?
C17 C18 C19 N2 0.9(7) . . . . ?
C17 C18 C19 C20 -179.0(4) . . . . ?
O1 C1 C2 C3 -177.2(4) . . . . ?
C6 C1 C2 C3 2.8(6) . . . . ?
C4 C3 C2 C1 1.1(6) . . . . ?
N2 C16 C15 C17 1.7(6) . . . . ?
C11 C16 C15 C17 -176.5(4) . . . . ?
N2 C16 C15 C14 -179.8(4) . . . . ?
C11 C16 C15 C14 2.0(6) . . . . ?
C13 C14 C15 C17 177.2(4) . . . . ?
C13 C14 C15 C16 -1.2(6) . . . . ?
C6 N1 C9 C8 -2.4(6) . . . . ?
C6 N1 C9 C10 179.2(4) . . . . ?
C19 C18 C17 C15 0.9(7) . . . . ?
C16 C15 C17 C18 -2.2(7) . . . . ?
C14 C15 C17 C18 179.4(4) . . . . ?
Y1 O2 C11 C12 71.4(12) . . . . ?
Y1 O2 C11 C16 -108.6(11) . . . . ?
N2 C16 C11 O2 -0.2(6) . . . . ?
C15 C16 C11 O2 178.1(4) . . . . ?
N2 C16 C11 C12 179.8(4) . . . . ?
C15 C16 C11 C12 -2.0(6) . . . . ?
N1 C6 C5 C4 -177.7(4) . . . . ?
C1 C6 C5 C4 3.3(7) . . . . ?
N1 C6 C5 C7 2.8(6) . . . . ?
C1 C6 C5 C7 -176.2(4) . . . . ?
C8 C7 C5 C4 179.1(4) . . . . ?
C8 C7 C5 C6 -1.5(7) . . . . ?
C5 C7 C8 C9 -1.9(7) . . . . ?
N1 C9 C8 C7 3.8(7) . . . . ?
C10 C9 C8 C7 -178.0(4) . . . . ?
O2 C11 C12 C13 -178.8(4) . . . . ?
C16 C11 C12 C13 1.2(6) . . . . ?
C15 C14 C13 C12 0.5(7) . . . . ?
C11 C12 C13 C14 -0.5(7) . . . . ?
C2 C3 C4 C5 -2.9(7) . . . . ?
C6 C5 C4 C3 0.7(7) . . . . ?
C7 C5 C4 C3 -179.8(4) . . . . ?
Y1 O9 N5 O11 -174.8(4) . . . . ?
Y1 O9 N5 O10 3.8(4) . . . . ?
Y1 O10 N5 O11 174.7(4) . . . . ?
Y1 O10 N5 O9 -3.8(4) . . . . ?
Y1 O6 N4 O8 -176.4(4) . . . . ?
Y1 O6 N4 O7 1.9(4) . . . . ?
Y1 O7 N4 O8 176.3(4) . . . . ?
Y1 O7 N4 O6 -2.0(4) . . . . ?

_refine_diff_density_max         0.765
_refine_diff_density_min         -0.610
_refine_diff_density_rms         0.138

####################################################################### 
# 
# 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 1871951'
_audit_update_record             
;
2018-11-13 deposited with the CCDC.
2018-11-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H36 N10 O22 Yb2'
_chemical_formula_weight         1354.87

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Yb Yb -0.3850 5.5486 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.600(3)
_cell_length_b                   18.102(4)
_cell_length_c                   12.383(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.001(3)
_cell_angle_gamma                90
_cell_volume                     2232.8(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5387
_cell_measurement_theta_min      3.0411
_cell_measurement_theta_max      27.4932

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.015
_exptl_crystal_F_000             1324
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    4.263
_shelx_estimated_absorpt_T_min   0.483
_shelx_estimated_absorpt_T_max   0.815
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7746
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   '(Higashi, 1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn 724+'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8887
_diffrn_reflns_av_unetI/netI     0.0852
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.022
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             5008
_reflns_number_gt                3485
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        
'CrystalClear (Rigaku Inc., 2008), SORTAV (Blessing, 1995)'
_computing_structure_solution    'SIR92 (Altomare et al, 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0030P)²+0.0500P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5008
_refine_ls_number_parameters     344
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0316
_refine_ls_wR_factor_ref         0.0675
_refine_ls_wR_factor_gt          0.0640
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Yb1 Yb 0.61543(2) 1.02151(2) 0.15345(2) 0.01330(7) Uani 1 1 d . . . . .
O3 O 0.7997(3) 1.10531(18) 0.1936(3) 0.0215(8) Uani 1 1 d . . . . .
O6 O 0.8287(3) 0.95378(18) 0.1908(3) 0.0190(8) Uani 1 1 d . . . . .
O1 O 0.6014(3) 0.97645(16) -0.0231(3) 0.0113(7) Uani 1 1 d . . . . .
O10 O 0.4962(3) 0.95875(18) 0.2655(3) 0.0198(8) Uani 1 1 d . . . . .
O4 O 0.6256(4) 1.13755(18) 0.0508(3) 0.0230(8) Uani 1 1 d . . . . .
O9 O 0.5849(3) 0.88758(18) 0.1713(3) 0.0206(8) Uani 1 1 d . . . . .
O7 O 0.7744(3) 0.98830(18) 0.3356(3) 0.0241(9) Uani 1 1 d . . . . .
O8 O 0.9586(4) 0.9251(2) 0.3653(3) 0.0333(10) Uani 1 1 d . . . . .
O2 O 0.5555(3) 1.10507(18) 0.2518(3) 0.0194(8) Uani 1 1 d . . . . .
O11 O 0.4624(4) 0.8397(2) 0.2640(4) 0.0371(11) Uani 1 1 d . . . . .
O5 O 0.7870(4) 1.2166(2) 0.1236(4) 0.0394(11) Uani 1 1 d . . . . .
N1 N 0.6828(4) 0.8309(2) -0.0045(4) 0.0176(10) Uani 1 1 d D . . . .
C10 C 0.6286(6) 0.7108(3) 0.0531(5) 0.0306(14) Uani 1 1 d . . . . .
H10A H 0.5931 0.7410 0.1018 0.046 Uiso 1 1 calc R U . . .
H10B H 0.6862 0.6719 0.0997 0.046 Uiso 1 1 calc R U . . .
H10C H 0.5540 0.6883 -0.0084 0.046 Uiso 1 1 calc R U . . .
N4 N 0.8563(4) 0.9547(2) 0.2980(4) 0.0230(10) Uani 1 1 d . . . . .
N5 N 0.5110(4) 0.8928(2) 0.2338(4) 0.0234(11) Uani 1 1 d . . . . .
C7 C 0.8766(5) 0.7820(3) -0.0831(5) 0.0247(13) Uani 1 1 d . . . . .
H7 H 0.9434 0.7635 -0.1111 0.030 Uiso 1 1 calc R U . . .
C3 C 0.8882(5) 0.9843(3) -0.1270(4) 0.0215(12) Uani 1 1 d . . . . .
H3 H 0.9385 1.0203 -0.1508 0.026 Uiso 1 1 calc R U . . .
C2 C 0.7810(5) 1.0071(3) -0.0916(4) 0.0154(11) Uani 1 1 d . . . . .
H2 H 0.7584 1.0580 -0.0939 0.018 Uiso 1 1 calc R U . . .
C8 C 0.8078(6) 0.7337(3) -0.0401(5) 0.0301(15) Uani 1 1 d . . . . .
H8A H 0.8273 0.6824 -0.0385 0.036 Uiso 1 1 calc R U . . .
C1 C 0.7096(4) 0.9568(2) -0.0541(4) 0.0122(10) Uani 1 1 d . . . . .
N3 N 0.7401(4) 1.1559(3) 0.1227(4) 0.0236(10) Uani 1 1 d . . . . .
C4 C 0.9204(5) 0.9121(3) -0.1275(5) 0.0250(13) Uani 1 1 d . . . . .
H4 H 0.9898 0.8976 -0.1553 0.030 Uiso 1 1 calc R U . . .
C9 C 0.7090(5) 0.7585(3) 0.0018(5) 0.0221(12) Uani 1 1 d . . . . .
C5 C 0.8523(5) 0.8587(3) -0.0874(4) 0.0214(12) Uani 1 1 d . . . . .
C6 C 0.7463(5) 0.8825(3) -0.0493(4) 0.0153(11) Uani 1 1 d . . . . .
C11 C 0.4961(5) 1.1623(3) 0.2790(5) 0.0174(11) Uani 1 1 d . . . . .
C16 C 0.4014(5) 1.1482(3) 0.3360(5) 0.0167(11) Uani 1 1 d . . . . .
C12 C 0.5177(5) 1.2358(3) 0.2600(4) 0.0187(12) Uani 1 1 d . . . . .
H12 H 0.5803 1.2476 0.2231 0.022 Uiso 1 1 calc R U . . .
N2 N 0.3789(4) 1.0766(2) 0.3589(4) 0.0156(9) Uani 1 1 d D . . . .
C20 C 0.2783(5) 0.9745(3) 0.4270(5) 0.0250(12) Uani 1 1 d . . . . .
H19A H 0.3244 0.9463 0.3840 0.038 Uiso 1 1 calc R U . . .
H19B H 0.1831 0.9610 0.4002 0.038 Uiso 1 1 calc R U . . .
H19C H 0.3187 0.9633 0.5091 0.038 Uiso 1 1 calc R U . . .
C13 C 0.4511(6) 1.2927(3) 0.2930(5) 0.0227(12) Uani 1 1 d . . . . .
H13 H 0.4705 1.3424 0.2796 0.027 Uiso 1 1 calc R U . . .
C19 C 0.2919(5) 1.0557(3) 0.4081(4) 0.0206(12) Uani 1 1 d . . . . .
C15 C 0.3316(5) 1.2048(3) 0.3691(5) 0.0207(12) Uani 1 1 d . . . . .
C18 C 0.2176(5) 1.1098(3) 0.4386(5) 0.0258(13) Uani 1 1 d . . . . .
H18 H 0.1542 1.0964 0.4739 0.031 Uiso 1 1 calc R U . . .
C14 C 0.3572(5) 1.2784(3) 0.3449(5) 0.0251(13) Uani 1 1 d . . . . .
H14 H 0.3100 1.3180 0.3643 0.030 Uiso 1 1 calc R U . . .
C17 C 0.2358(5) 1.1825(3) 0.4176(5) 0.0267(13) Uani 1 1 d . . . . .
H17 H 0.1822 1.2189 0.4365 0.032 Uiso 1 1 calc R U . . .
H2A H 0.431(4) 1.044(2) 0.345(5) 0.024(16) Uiso 1 1 d D . . . .
H1A H 0.625(4) 0.844(3) 0.023(4) 0.024(16) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Yb1 O2 2.169(3) . ?
Yb1 O1 2.291(3) . ?
Yb1 O1 2.313(3) 3_675 ?
Yb1 O7 2.385(4) . ?
Yb1 O3 2.387(3) . ?
Yb1 O10 2.452(3) . ?
Yb1 O9 2.466(3) . ?
Yb1 O6 2.473(3) . ?
Yb1 O4 2.477(3) . ?
Yb1 Yb1 3.8308(9) 3_675 ?
O3 N3 1.277(5) . ?
O6 N4 1.258(5) . ?
O1 C1 1.375(5) . ?
O1 Yb1 2.313(3) 3_675 ?
O10 N5 1.283(5) . ?
O4 N3 1.280(5) . ?
O9 N5 1.279(5) . ?
O7 N4 1.272(5) . ?
O8 N4 1.241(5) . ?
O2 C11 1.314(6) . ?
O11 N5 1.208(5) . ?
O5 N3 1.204(5) . ?
N1 C9 1.338(6) . ?
N1 C6 1.374(6) . ?
N1 H1A 0.837(19) . ?
C10 C9 1.498(7) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C7 C8 1.359(7) . ?
C7 C5 1.410(7) . ?
C7 H7 0.9500 . ?
C3 C4 1.352(7) . ?
C3 C2 1.412(6) . ?
C3 H3 0.9500 . ?
C2 C1 1.362(6) . ?
C2 H2 0.9500 . ?
C8 C9 1.392(7) . ?
C8 H8A 0.9500 . ?
C1 C6 1.395(6) . ?
C4 C5 1.395(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.427(6) . ?
C11 C12 1.383(6) . ?
C11 C16 1.434(6) . ?
C16 N2 1.367(6) . ?
C16 C15 1.403(6) . ?
C12 C13 1.387(7) . ?
C12 H12 0.9500 . ?
N2 C19 1.323(6) . ?
N2 H2A 0.865(19) . ?
C20 C19 1.504(7) . ?
C20 H19A 0.9800 . ?
C20 H19B 0.9800 . ?
C20 H19C 0.9800 . ?
C13 C14 1.382(7) . ?
C13 H13 0.9500 . ?
C19 C18 1.387(7) . ?
C15 C17 1.405(7) . ?
C15 C14 1.413(7) . ?
C18 C17 1.367(7) . ?
C18 H18 0.9500 . ?
C14 H14 0.9500 . ?
C17 H17 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
O2 Yb1 O1 148.05(12) . . ?
O2 Yb1 O1 88.20(12) . 3_675 ?
O1 Yb1 O1 67.35(12) . 3_675 ?
O2 Yb1 O7 83.83(12) . . ?
O1 Yb1 O7 127.41(11) . . ?
O1 Yb1 O7 151.13(11) 3_675 . ?
O2 Yb1 O3 79.38(12) . . ?
O1 Yb1 O3 101.93(12) . . ?
O1 Yb1 O3 133.01(12) 3_675 . ?
O7 Yb1 O3 72.55(12) . . ?
O2 Yb1 O10 72.45(12) . . ?
O1 Yb1 O10 119.84(11) . . ?
O1 Yb1 O10 79.67(12) 3_675 . ?
O7 Yb1 O10 71.47(12) . . ?
O3 Yb1 O10 136.03(13) . . ?
O2 Yb1 O9 124.23(12) . . ?
O1 Yb1 O9 76.58(11) . . ?
O1 Yb1 O9 87.06(11) 3_675 . ?
O7 Yb1 O9 74.89(12) . . ?
O3 Yb1 O9 136.82(11) . . ?
O10 Yb1 O9 52.05(10) . . ?
O2 Yb1 O6 131.72(13) . . ?
O1 Yb1 O6 76.04(11) . . ?
O1 Yb1 O6 139.93(11) 3_675 . ?
O7 Yb1 O6 52.64(11) . . ?
O3 Yb1 O6 69.24(11) . . ?
O10 Yb1 O6 106.25(11) . . ?
O9 Yb1 O6 68.62(11) . . ?
O2 Yb1 O4 76.66(12) . . ?
O1 Yb1 O4 79.17(11) . . ?
O1 Yb1 O4 80.54(11) 3_675 . ?
O7 Yb1 O4 123.95(12) . . ?
O3 Yb1 O4 52.54(12) . . ?
O10 Yb1 O4 143.57(11) . . ?
O9 Yb1 O4 155.51(12) . . ?
O6 Yb1 O4 108.60(11) . . ?
O2 Yb1 Yb1 119.23(10) . 3_675 ?
O1 Yb1 Yb1 33.86(7) . 3_675 ?
O1 Yb1 Yb1 33.49(7) 3_675 3_675 ?
O7 Yb1 Yb1 153.12(8) . 3_675 ?
O3 Yb1 Yb1 122.37(9) . 3_675 ?
O10 Yb1 Yb1 100.91(9) . 3_675 ?
O9 Yb1 Yb1 80.23(9) . 3_675 ?
O6 Yb1 Yb1 108.53(8) . 3_675 ?
O4 Yb1 Yb1 77.78(9) . 3_675 ?
N3 O3 Yb1 97.8(3) . . ?
N4 O6 Yb1 93.4(3) . . ?
C1 O1 Yb1 124.8(3) . . ?
C1 O1 Yb1 122.3(3) . 3_675 ?
Yb1 O1 Yb1 112.65(12) . 3_675 ?
N5 O10 Yb1 96.7(3) . . ?
N3 O4 Yb1 93.5(3) . . ?
N5 O9 Yb1 96.2(3) . . ?
N4 O7 Yb1 97.1(3) . . ?
C11 O2 Yb1 162.1(3) . . ?
C9 N1 C6 124.7(4) . . ?
C9 N1 H1A 115(3) . . ?
C6 N1 H1A 120(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O8 N4 O6 122.5(4) . . ?
O8 N4 O7 120.6(5) . . ?
O6 N4 O7 116.8(4) . . ?
O11 N5 O9 122.8(5) . . ?
O11 N5 O10 122.4(4) . . ?
O9 N5 O10 114.8(4) . . ?
C8 C7 C5 122.2(5) . . ?
C8 C7 H7 118.9 . . ?
C5 C7 H7 118.9 . . ?
C4 C3 C2 121.0(5) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C1 C2 C3 120.7(5) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C7 C8 C9 120.8(5) . . ?
C7 C8 H8A 119.6 . . ?
C9 C8 H8A 119.6 . . ?
C2 C1 O1 122.4(4) . . ?
C2 C1 C6 118.7(4) . . ?
O1 C1 C6 118.9(4) . . ?
O5 N3 O3 122.9(5) . . ?
O5 N3 O4 122.3(5) . . ?
O3 N3 O4 114.9(4) . . ?
C3 C4 C5 120.4(5) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
N1 C9 C8 117.5(5) . . ?
N1 C9 C10 116.9(5) . . ?
C8 C9 C10 125.6(5) . . ?
C4 C5 C7 125.8(5) . . ?
C4 C5 C6 118.1(5) . . ?
C7 C5 C6 116.1(5) . . ?
N1 C6 C1 120.3(4) . . ?
N1 C6 C5 118.6(4) . . ?
C1 C6 C5 121.1(5) . . ?
O2 C11 C12 126.3(5) . . ?
O2 C11 C16 117.6(4) . . ?
C12 C11 C16 116.1(4) . . ?
N2 C16 C15 119.0(4) . . ?
N2 C16 C11 118.1(4) . . ?
C15 C16 C11 122.8(5) . . ?
C11 C12 C13 122.2(5) . . ?
C11 C12 H12 118.9 . . ?
C13 C12 H12 118.9 . . ?
C19 N2 C16 124.4(4) . . ?
C19 N2 H2A 119(3) . . ?
C16 N2 H2A 116(3) . . ?
C19 C20 H19A 109.5 . . ?
C19 C20 H19B 109.5 . . ?
H19A C20 H19B 109.5 . . ?
C19 C20 H19C 109.5 . . ?
H19A C20 H19C 109.5 . . ?
H19B C20 H19C 109.5 . . ?
C14 C13 C12 121.2(5) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
N2 C19 C18 118.3(5) . . ?
N2 C19 C20 118.0(4) . . ?
C18 C19 C20 123.7(4) . . ?
C16 C15 C17 116.5(5) . . ?
C16 C15 C14 117.9(5) . . ?
C17 C15 C14 125.5(5) . . ?
C17 C18 C19 119.8(5) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C13 C14 C15 119.7(5) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C18 C17 C15 121.8(5) . . ?
C18 C17 H17 119.1 . . ?
C15 C17 H17 119.1 . . ?

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 O6 N4 O8 178.5(4) . . . . ?
Yb1 O6 N4 O7 -2.2(4) . . . . ?
Yb1 O7 N4 O8 -178.4(4) . . . . ?
Yb1 O7 N4 O6 2.3(4) . . . . ?
Yb1 O9 N5 O11 176.9(4) . . . . ?
Yb1 O9 N5 O10 -5.4(4) . . . . ?
Yb1 O10 N5 O11 -176.9(4) . . . . ?
Yb1 O10 N5 O9 5.5(4) . . . . ?
C4 C3 C2 C1 1.7(8) . . . . ?
C5 C7 C8 C9 0.1(9) . . . . ?
C3 C2 C1 O1 -177.5(4) . . . . ?
C3 C2 C1 C6 1.3(7) . . . . ?
Yb1 O1 C1 C2 -83.3(5) . . . . ?
Yb1 O1 C1 C2 90.1(5) 3_675 . . . ?
Yb1 O1 C1 C6 98.0(4) . . . . ?
Yb1 O1 C1 C6 -88.7(5) 3_675 . . . ?
Yb1 O3 N3 O5 167.9(4) . . . . ?
Yb1 O3 N3 O4 -11.4(4) . . . . ?
Yb1 O4 N3 O5 -168.4(4) . . . . ?
Yb1 O4 N3 O3 10.9(4) . . . . ?
C2 C3 C4 C5 -3.3(8) . . . . ?
C6 N1 C9 C8 0.1(8) . . . . ?
C6 N1 C9 C10 -179.7(5) . . . . ?
C7 C8 C9 N1 1.5(8) . . . . ?
C7 C8 C9 C10 -178.7(5) . . . . ?
C3 C4 C5 C7 -179.8(5) . . . . ?
C3 C4 C5 C6 1.7(8) . . . . ?
C8 C7 C5 C4 178.4(6) . . . . ?
C8 C7 C5 C6 -3.1(8) . . . . ?
C9 N1 C6 C1 178.6(5) . . . . ?
C9 N1 C6 C5 -3.1(8) . . . . ?
C2 C1 C6 N1 175.4(5) . . . . ?
O1 C1 C6 N1 -5.8(7) . . . . ?
C2 C1 C6 C5 -2.8(7) . . . . ?
O1 C1 C6 C5 176.0(4) . . . . ?
C4 C5 C6 N1 -176.9(5) . . . . ?
C7 C5 C6 N1 4.4(7) . . . . ?
C4 C5 C6 C1 1.3(8) . . . . ?
C7 C5 C6 C1 -177.4(5) . . . . ?
Yb1 O2 C11 C12 -69.6(12) . . . . ?
Yb1 O2 C11 C16 111.7(10) . . . . ?
O2 C11 C16 N2 0.2(7) . . . . ?
C12 C11 C16 N2 -178.6(5) . . . . ?
O2 C11 C16 C15 -179.9(5) . . . . ?
C12 C11 C16 C15 1.3(8) . . . . ?
O2 C11 C12 C13 -179.2(5) . . . . ?
C16 C11 C12 C13 -0.5(8) . . . . ?
C15 C16 N2 C19 2.0(8) . . . . ?
C11 C16 N2 C19 -178.1(5) . . . . ?
C11 C12 C13 C14 -1.3(9) . . . . ?
C16 N2 C19 C18 0.2(8) . . . . ?
C16 N2 C19 C20 179.7(5) . . . . ?
N2 C16 C15 C17 -4.0(8) . . . . ?
C11 C16 C15 C17 176.1(5) . . . . ?
N2 C16 C15 C14 179.7(5) . . . . ?
C11 C16 C15 C14 -0.2(8) . . . . ?
N2 C19 C18 C17 -0.1(8) . . . . ?
C20 C19 C18 C17 -179.6(5) . . . . ?
C12 C13 C14 C15 2.4(9) . . . . ?
C16 C15 C14 C13 -1.7(8) . . . . ?
C17 C15 C14 C13 -177.6(6) . . . . ?
C19 C18 C17 C15 -2.1(9) . . . . ?
C16 C15 C17 C18 4.2(8) . . . . ?
C14 C15 C17 C18 -179.8(6) . . . . ?

_refine_diff_density_max         1.964
_refine_diff_density_min         -1.029
_refine_diff_density_rms         0.172

