# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1941861'
loop_
_audit_author_name
_audit_author_address
'XueMei Zhang'
;Tianjin University
China
;
_audit_update_record             
;
2020-10-06 deposited with the CCDC.	2020-10-09 downloaded from the CCDC.
;
_audit_creation_date             2020-09-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H20 Dy N3 O6, C3 H8 O'
_chemical_formula_sum            'C22 H28 Dy N3 O7'
_chemical_formula_weight         608.97
_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'
Dy Dy -0.1892 4.4098 '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                   11.311(2)
_cell_length_b                   14.748(3)
_cell_length_c                   15.539(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.92(3)
_cell_angle_gamma                90
_cell_volume                     2437.0(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6627
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      28.1199
_cell_measurement_theta_min      2.3612
_shelx_estimated_absorpt_T_max   0.707
_shelx_estimated_absorpt_T_min   0.636
_exptl_absorpt_coefficient_mu    3.111
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8431
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1212
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            28867
_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         27.895
_diffrn_reflns_theta_min         2.361
_diffrn_ambient_temperature      113.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5018
_reflns_number_total             5815
_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       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         1.170
_refine_diff_density_min         -1.466
_refine_diff_density_rms         0.135
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         5815
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0273
_refine_ls_restrained_S_all      1.101
_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)+(0.0358P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0630
_refine_ls_wR_factor_ref         0.0655
_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, All O(H) groups, All O(H,H) groups
2.a Riding coordinates:
 O6(H6A,H6B), O7(H7A)
2.b Ternary CH refined with riding coordinates:
 C21(H21)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C9(H9), C10(H10), C11(H11), C17(H17)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
Dy1 Dy 0.65640(2) 0.43750(2) 0.07340(2) 0.01078(5) Uani 1 1 d . . . . .
O1 O 0.56612(17) 0.57068(11) -0.00635(13) 0.0135(4) Uani 1 1 d . . . . .
O2 O 0.81817(17) 0.45555(12) 0.20632(12) 0.0141(4) Uani 1 1 d . . . . .
O3 O 0.96063(19) 0.38134(14) 0.35908(13) 0.0245(5) Uani 1 1 d . . . . .
O4 O 0.62863(18) 0.39934(13) -0.08091(13) 0.0183(4) Uani 1 1 d . . . . .
O5 O 0.79667(18) 0.32320(12) 0.07345(12) 0.0174(4) Uani 1 1 d . . . . .
O6 O 0.57012(19) 0.50060(14) 0.17879(13) 0.0247(5) Uani 1 1 d . . . . .
H6A H 0.508926 0.537658 0.162403 0.037 Uiso 1 1 d R U . . .
H6B H 0.613186 0.508888 0.234503 0.037 Uiso 1 1 d R U . . .
N1 N 0.4435(2) 0.69960(14) -0.11916(14) 0.0148(4) Uani 1 1 d . . . . .
N2 N 0.7574(2) 0.61804(15) -0.01551(15) 0.0154(5) Uani 1 1 d . . . . .
N3 N 0.8037(2) 0.54665(15) 0.04778(15) 0.0137(4) Uani 1 1 d . . . . .
C1 C 0.3782(3) 0.76825(18) -0.17056(18) 0.0178(5) Uani 1 1 d . . . . .
H1 H 0.289646 0.769746 -0.184469 0.021 Uiso 1 1 calc R U . . .
C2 C 0.4339(3) 0.83701(18) -0.2042(2) 0.0214(6) Uani 1 1 d . . . . .
H2 H 0.384799 0.884449 -0.240531 0.026 Uiso 1 1 calc R U . . .
C3 C 0.5629(3) 0.83462(19) -0.1835(2) 0.0244(6) Uani 1 1 d . . . . .
H3 H 0.603840 0.880953 -0.205337 0.029 Uiso 1 1 calc R U . . .
C4 C 0.6320(3) 0.76459(19) -0.13104(19) 0.0206(6) Uani 1 1 d . . . . .
H4 H 0.720513 0.761444 -0.117066 0.025 Uiso 1 1 calc R U . . .
C5 C 0.5688(2) 0.69841(17) -0.09891(17) 0.0135(5) Uani 1 1 d . . . . .
C6 C 0.6362(2) 0.62357(17) -0.03692(16) 0.0127(5) Uani 1 1 d . . . . .
C7 C 0.9252(3) 0.54135(18) 0.07989(18) 0.0151(5) Uani 1 1 d . . . . .
H7 H 0.971806 0.577629 0.052270 0.018 Uiso 1 1 calc R U . . .
C8 C 0.9942(2) 0.48320(17) 0.15559(17) 0.0140(5) Uani 1 1 d . . . . .
C9 C 1.1239(3) 0.47080(19) 0.17225(19) 0.0177(5) Uani 1 1 d . . . . .
H9 H 1.160068 0.493791 0.129779 0.021 Uiso 1 1 calc R U . . .
C10 C 1.1983(3) 0.42601(19) 0.2489(2) 0.0226(6) Uani 1 1 d . . . . .
H10 H 1.284656 0.415749 0.258193 0.027 Uiso 1 1 calc R U . . .
C11 C 1.1458(3) 0.3953(2) 0.3139(2) 0.0214(6) Uani 1 1 d . . . . .
H11 H 1.197954 0.366531 0.368239 0.026 Uiso 1 1 calc R U . . .
C12 C 1.0197(3) 0.40668(19) 0.29926(19) 0.0174(5) Uani 1 1 d . . . . .
C13 C 0.9376(2) 0.44806(16) 0.21759(18) 0.0133(5) Uani 1 1 d . . . . .
C14 C 1.0373(3) 0.3480(2) 0.4462(2) 0.0339(8) Uani 1 1 d . . . . .
H14A H 1.078273 0.291634 0.438145 0.051 Uiso 1 1 calc R U . . .
H14B H 0.984999 0.336187 0.483887 0.051 Uiso 1 1 calc R U . . .
H14C H 1.101521 0.393206 0.476466 0.051 Uiso 1 1 calc R U . . .
C15 C 0.6390(3) 0.3528(2) -0.22421(19) 0.0267(7) Uani 1 1 d . . . . .
H15A H 0.556086 0.323794 -0.243446 0.040 Uiso 1 1 calc R U . . .
H15B H 0.695223 0.318091 -0.247808 0.040 Uiso 1 1 calc R U . . .
H15C H 0.630670 0.414751 -0.248376 0.040 Uiso 1 1 calc R U . . .
C16 C 0.6927(3) 0.35555(18) -0.12111(18) 0.0163(5) Uani 1 1 d . . . . .
C17 C 0.8042(3) 0.31028(19) -0.07613(18) 0.0178(5) Uani 1 1 d . . . . .
H17 H 0.851420 0.287597 -0.111616 0.021 Uiso 1 1 calc R U . . .
C18 C 0.8511(3) 0.29603(18) 0.01889(19) 0.0176(6) Uani 1 1 d . . . . .
C19 C 0.9722(3) 0.2448(2) 0.0606(2) 0.0286(7) Uani 1 1 d . . . . .
H19A H 1.033714 0.283757 0.104846 0.043 Uiso 1 1 calc R U . . .
H19B H 1.004889 0.226651 0.012375 0.043 Uiso 1 1 calc R U . . .
H19C H 0.956762 0.190728 0.091867 0.043 Uiso 1 1 calc R U . . .
O7 O 0.76732(19) 0.99862(15) 0.14665(13) 0.0260(5) Uani 1 1 d . . . . .
H7A H 0.708814 0.969052 0.156559 0.039 Uiso 1 1 d R U . . .
C20 C 0.8224(4) 0.8445(2) 0.1195(3) 0.0380(8) Uani 1 1 d . . . . .
H20A H 0.906110 0.849109 0.166328 0.057 Uiso 1 1 calc R U . . .
H20B H 0.825607 0.802816 0.071253 0.057 Uiso 1 1 calc R U . . .
H20C H 0.762644 0.821487 0.147483 0.057 Uiso 1 1 calc R U . . .
C21 C 0.7807(3) 0.93666(19) 0.0789(2) 0.0252(7) Uani 1 1 d . . . . .
H21 H 0.697669 0.930547 0.028732 0.030 Uiso 1 1 calc R U . . .
C22 C 0.8737(4) 0.9799(3) 0.0403(3) 0.0412(9) Uani 1 1 d . . . . .
H22A H 0.842577 1.039591 0.014960 0.062 Uiso 1 1 calc R U . . .
H22B H 0.883337 0.941197 -0.008207 0.062 Uiso 1 1 calc R U . . .
H22C H 0.955320 0.986697 0.089114 0.062 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
Dy1 Dy1 3.9522(12) 3_665 ?
Dy1 O1 2.3610(17) . ?
Dy1 O1 2.377(2) 3_665 ?
Dy1 O2 2.260(2) . ?
Dy1 O4 2.3773(19) . ?
Dy1 O5 2.3149(18) . ?
Dy1 O6 2.364(2) . ?
Dy1 N1 2.534(2) 3_665 ?
Dy1 N3 2.445(2) . ?
O1 C6 1.311(3) . ?
O2 C13 1.306(3) . ?
O3 C12 1.368(3) . ?
O3 C14 1.423(3) . ?
O4 C16 1.281(3) . ?
O5 C18 1.271(3) . ?
O6 H6A 0.8500 . ?
O6 H6B 0.8451 . ?
N1 C1 1.344(3) . ?
N1 C5 1.343(3) . ?
N2 N3 1.414(3) . ?
N2 C6 1.299(3) . ?
N3 C7 1.295(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.387(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.384(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.382(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.399(4) . ?
C5 C6 1.492(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.450(4) . ?
C8 C9 1.411(4) . ?
C8 C13 1.424(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.372(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.408(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.377(4) . ?
C12 C13 1.429(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C15 C16 1.508(4) . ?
C16 C17 1.386(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.404(4) . ?
C18 C19 1.503(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O7 H7A 0.8493 . ?
O7 C21 1.440(4) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C20 C21 1.505(4) . ?
C21 H21 1.0000 . ?
C21 C22 1.518(4) . ?
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 Dy1 Dy1 33.34(4) 3_665 3_665 ?
O1 Dy1 Dy1 33.59(4) . 3_665 ?
O1 Dy1 O1 66.93(7) . 3_665 ?
O1 Dy1 O4 77.85(7) 3_665 . ?
O1 Dy1 O4 77.44(7) . . ?
O1 Dy1 O6 80.18(7) . . ?
O1 Dy1 N1 64.88(7) 3_665 3_665 ?
O1 Dy1 N1 131.06(7) . 3_665 ?
O1 Dy1 N3 64.12(7) . . ?
O1 Dy1 N3 129.84(7) 3_665 . ?
O2 Dy1 Dy1 139.39(5) . 3_665 ?
O2 Dy1 O1 116.89(6) . . ?
O2 Dy1 O1 144.41(7) . 3_665 ?
O2 Dy1 O4 137.49(7) . . ?
O2 Dy1 O5 75.18(7) . . ?
O2 Dy1 O6 73.58(7) . . ?
O2 Dy1 N1 97.88(7) . 3_665 ?
O2 Dy1 N3 71.76(7) . . ?
O4 Dy1 Dy1 75.14(5) . 3_665 ?
O4 Dy1 N1 100.13(7) . 3_665 ?
O4 Dy1 N3 81.65(7) . . ?
O5 Dy1 Dy1 144.94(5) . 3_665 ?
O5 Dy1 O1 125.91(6) . 3_665 ?
O5 Dy1 O1 141.24(7) . . ?
O5 Dy1 O4 71.51(7) . . ?
O5 Dy1 O6 136.98(7) . . ?
O5 Dy1 N1 77.88(7) . 3_665 ?
O5 Dy1 N3 88.55(7) . . ?
O6 Dy1 Dy1 73.54(5) . 3_665 ?
O6 Dy1 O1 72.43(7) . 3_665 ?
O6 Dy1 O4 147.99(7) . . ?
O6 Dy1 N1 77.92(7) . 3_665 ?
O6 Dy1 N3 108.58(8) . . ?
N1 Dy1 Dy1 97.88(5) 3_665 3_665 ?
N3 Dy1 Dy1 97.15(5) . 3_665 ?
N3 Dy1 N1 164.82(7) . 3_665 ?
Dy1 O1 Dy1 113.07(7) . 3_665 ?
C6 O1 Dy1 118.58(16) . . ?
C6 O1 Dy1 123.51(15) . 3_665 ?
C13 O2 Dy1 126.20(16) . . ?
C12 O3 C14 117.4(2) . . ?
C16 O4 Dy1 135.14(17) . . ?
C18 O5 Dy1 135.84(18) . . ?
Dy1 O6 H6A 122.1 . . ?
Dy1 O6 H6B 122.4 . . ?
H6A O6 H6B 109.9 . . ?
C1 N1 Dy1 124.08(18) . 3_665 ?
C5 N1 Dy1 117.37(17) . 3_665 ?
C5 N1 C1 118.1(2) . . ?
C6 N2 N3 109.4(2) . . ?
N2 N3 Dy1 119.53(16) . . ?
C7 N3 Dy1 126.17(18) . . ?
C7 N3 N2 113.9(2) . . ?
N1 C1 H1 118.4 . . ?
N1 C1 C2 123.1(3) . . ?
C2 C1 H1 118.4 . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118.2(3) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.8 . . ?
C3 C4 C5 118.5(3) . . ?
C5 C4 H4 120.8 . . ?
N1 C5 C4 122.3(2) . . ?
N1 C5 C6 115.3(2) . . ?
C4 C5 C6 122.4(2) . . ?
O1 C6 C5 115.8(2) . . ?
N2 C6 O1 125.9(2) . . ?
N2 C6 C5 118.3(2) . . ?
N3 C7 H7 118.1 . . ?
N3 C7 C8 123.7(2) . . ?
C8 C7 H7 118.1 . . ?
C9 C8 C7 117.6(2) . . ?
C9 C8 C13 120.5(2) . . ?
C13 C8 C7 121.5(2) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.9(3) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.6(3) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.6(3) . . ?
C12 C11 H11 119.7 . . ?
O3 C12 C11 125.0(3) . . ?
O3 C12 C13 113.6(2) . . ?
C11 C12 C13 121.4(3) . . ?
O2 C13 C8 124.2(2) . . ?
O2 C13 C12 119.0(2) . . ?
C8 C13 C12 116.8(2) . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C16 C15 H15C 109.5 . . ?
O4 C16 C15 116.2(2) . . ?
O4 C16 C17 124.4(2) . . ?
C17 C16 C15 119.4(2) . . ?
C16 C17 H17 118.1 . . ?
C16 C17 C18 123.7(2) . . ?
C18 C17 H17 118.1 . . ?
O5 C18 C17 124.0(3) . . ?
O5 C18 C19 116.6(3) . . ?
C17 C18 C19 119.4(3) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 O7 H7A 95.1 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
C21 C20 H20C 109.5 . . ?
O7 C21 C20 111.3(3) . . ?
O7 C21 H21 108.8 . . ?
O7 C21 C22 106.4(3) . . ?
C20 C21 H21 108.8 . . ?
C20 C21 C22 112.6(3) . . ?
C22 C21 H21 108.8 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 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
Dy1 O1 C6 N2 -11.7(3) . . . . ?
Dy1 O1 C6 N2 -165.3(2) 3_665 . . . ?
Dy1 O1 C6 C5 17.2(3) 3_665 . . . ?
Dy1 O1 C6 C5 170.79(16) . . . . ?
Dy1 O2 C13 C8 42.0(3) . . . . ?
Dy1 O2 C13 C12 -141.7(2) . . . . ?
Dy1 O4 C16 C15 -176.81(19) . . . . ?
Dy1 O4 C16 C17 4.6(4) . . . . ?
Dy1 O5 C18 C17 -25.0(4) . . . . ?
Dy1 O5 C18 C19 155.8(2) . . . . ?
Dy1 N1 C1 C2 -171.8(2) 3_665 . . . ?
Dy1 N1 C5 C4 171.6(2) 3_665 . . . ?
Dy1 N1 C5 C6 -10.6(3) 3_665 . . . ?
Dy1 N3 C7 C8 -17.2(4) . . . . ?
O3 C12 C13 O2 -1.8(4) . . . . ?
O3 C12 C13 C8 174.8(2) . . . . ?
O4 C16 C17 C18 9.4(4) . . . . ?
N1 C1 C2 C3 -0.2(4) . . . . ?
N1 C5 C6 O1 -3.0(3) . . . . ?
N1 C5 C6 N2 179.2(2) . . . . ?
N2 N3 C7 C8 170.1(2) . . . . ?
N3 N2 C6 O1 -1.1(4) . . . . ?
N3 N2 C6 C5 176.4(2) . . . . ?
N3 C7 C8 C9 168.1(3) . . . . ?
N3 C7 C8 C13 -19.0(4) . . . . ?
C1 N1 C5 C4 -1.4(4) . . . . ?
C1 N1 C5 C6 176.4(2) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C2 C3 C4 C5 -1.0(4) . . . . ?
C3 C4 C5 N1 1.6(4) . . . . ?
C3 C4 C5 C6 -176.0(3) . . . . ?
C4 C5 C6 O1 174.7(2) . . . . ?
C4 C5 C6 N2 -3.0(4) . . . . ?
C5 N1 C1 C2 0.7(4) . . . . ?
C6 N2 N3 Dy1 13.0(3) . . . . ?
C6 N2 N3 C7 -173.8(2) . . . . ?
C7 C8 C9 C10 172.0(3) . . . . ?
C7 C8 C13 O2 8.3(4) . . . . ?
C7 C8 C13 C12 -168.1(2) . . . . ?
C8 C9 C10 C11 -2.7(4) . . . . ?
C9 C8 C13 O2 -179.0(2) . . . . ?
C9 C8 C13 C12 4.6(4) . . . . ?
C9 C10 C11 C12 2.6(5) . . . . ?
C10 C11 C12 O3 -178.3(3) . . . . ?
C10 C11 C12 C13 1.2(4) . . . . ?
C11 C12 C13 O2 178.6(3) . . . . ?
C11 C12 C13 C8 -4.7(4) . . . . ?
C13 C8 C9 C10 -1.0(4) . . . . ?
C14 O3 C12 C11 5.7(4) . . . . ?
C14 O3 C12 C13 -173.8(3) . . . . ?
C15 C16 C17 C18 -169.1(3) . . . . ?
C16 C17 C18 O5 -0.1(4) . . . . ?
C16 C17 C18 C19 179.1(3) . . . . ?

_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_shelxl_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1941862'
loop_
_audit_author_name
_audit_author_address
'XueMei Zhang'
;Tianjin University
China
;
_audit_update_record             
;
2020-10-06 deposited with the CCDC.	2020-10-09 downloaded from the CCDC.
;
_audit_creation_date             2020-09-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H24 Dy N3 O6'
_chemical_formula_sum            'C21 H24 Dy N3 O6'
_chemical_formula_weight         576.93
_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'
Dy Dy -0.1892 4.4098 '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                   9.0155(18)
_cell_length_b                   10.725(2)
_cell_length_c                   11.835(2)
_cell_angle_alpha                89.52(3)
_cell_angle_beta                 86.23(3)
_cell_angle_gamma                77.98(3)
_cell_volume                     1116.8(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3604
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9424
_cell_measurement_theta_min      1.7243
_shelx_estimated_absorpt_T_max   0.581
_shelx_estimated_absorpt_T_min   0.473
_exptl_absorpt_coefficient_mu    3.386
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7343
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.716
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             570
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_Laue_measured_fraction_full 0.998
_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       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13313
_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         27.892
_diffrn_reflns_theta_min         1.724
_diffrn_ambient_temperature      113.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4718
_reflns_number_total             5289
_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       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         1.966
_refine_diff_density_min         -1.649
_refine_diff_density_rms         0.142
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         5289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0316
_refine_ls_restrained_S_all      1.060
_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)+(0.0346P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0669
_refine_ls_wR_factor_ref         0.0695
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 O6(H6), C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C9(H9), C10(H10), C11(H11),
 C17(H17)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C19(H19A,H19B,H19C), C21(H21A,H21B,
 H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Dy1 Dy 0.37418(2) 0.59291(2) 0.62566(2) 0.01775(6) Uani 1 1 d . . . . .
O1 O 0.3829(2) 0.4532(2) 0.4727(2) 0.0178(5) Uani 1 1 d . . . . .
O2 O 0.6563(3) 0.3887(2) 0.1892(2) 0.0248(5) Uani 1 1 d . . . . .
O3 O 0.8881(3) 0.3487(3) 0.0383(3) 0.0386(7) Uani 1 1 d . . . . .
O4 O 0.1614(3) 0.7570(2) 0.6581(2) 0.0250(5) Uani 1 1 d . . . . .
O5 O 0.3715(3) 0.7460(2) 0.4794(2) 0.0218(5) Uani 1 1 d . . . . .
O6 O 0.4941(3) 0.3908(2) 0.6970(2) 0.0271(6) Uani 1 1 d . . . . .
H6 H 0.523830 0.327222 0.639829 0.033 Uiso 1 1 calc R U . . .
N1 N 0.1583(3) 0.4767(3) 0.6287(3) 0.0218(6) Uani 1 1 d . . . . .
N2 N 0.3102(3) 0.2838(3) 0.3865(3) 0.0207(6) Uani 1 1 d . . . . .
N3 N 0.4423(3) 0.2850(3) 0.3154(3) 0.0208(6) Uani 1 1 d . . . . .
C1 C 0.0423(4) 0.4971(4) 0.7068(3) 0.0286(8) Uani 1 1 d . . . . .
H1 H 0.038976 0.560259 0.763289 0.034 Uiso 1 1 calc R U . . .
C2 C -0.0735(4) 0.4300(4) 0.7091(4) 0.0318(9) Uani 1 1 d . . . . .
H2 H -0.154995 0.447043 0.765723 0.038 Uiso 1 1 calc R U . . .
C3 C -0.0679(4) 0.3380(4) 0.6274(4) 0.0311(9) Uani 1 1 d . . . . .
H3 H -0.145838 0.290557 0.627289 0.037 Uiso 1 1 calc R U . . .
C4 C 0.0509(4) 0.3151(3) 0.5461(3) 0.0250(8) Uani 1 1 d . . . . .
H4 H 0.056254 0.251737 0.489520 0.030 Uiso 1 1 calc R U . . .
C5 C 0.1629(4) 0.3865(3) 0.5484(3) 0.0192(7) Uani 1 1 d . . . . .
C6 C 0.2937(4) 0.3734(3) 0.4635(3) 0.0186(7) Uani 1 1 d . . . . .
C7 C 0.4610(4) 0.2068(3) 0.2306(3) 0.0251(8) Uani 1 1 d . . . . .
H7 H 0.386859 0.156704 0.222557 0.030 Uiso 1 1 calc R U . . .
C8 C 0.5885(4) 0.1912(3) 0.1470(3) 0.0242(7) Uani 1 1 d . . . . .
C9 C 0.6184(5) 0.0798(4) 0.0793(3) 0.0311(9) Uani 1 1 d . . . . .
H9 H 0.554702 0.019686 0.088774 0.037 Uiso 1 1 calc R U . . .
C10 C 0.7395(5) 0.0577(4) -0.0004(4) 0.0386(10) Uani 1 1 d . . . . .
H10 H 0.759637 -0.018041 -0.044900 0.046 Uiso 1 1 calc R U . . .
C11 C 0.8322(5) 0.1459(4) -0.0160(4) 0.0366(10) Uani 1 1 d . . . . .
H11 H 0.915755 0.129850 -0.070905 0.044 Uiso 1 1 calc R U . . .
C12 C 0.8036(4) 0.2564(4) 0.0476(3) 0.0277(8) Uani 1 1 d . . . . .
C13 C 0.6799(4) 0.2838(3) 0.1306(3) 0.0238(7) Uani 1 1 d . . . . .
C14 C 1.0373(5) 0.3150(5) -0.0132(4) 0.0482(12) Uani 1 1 d . . . . .
H14A H 1.095110 0.242104 0.026446 0.072 Uiso 1 1 calc R U . . .
H14B H 1.087329 0.387512 -0.009077 0.072 Uiso 1 1 calc R U . . .
H14C H 1.032578 0.292158 -0.092726 0.072 Uiso 1 1 calc R U . . .
C15 C 0.0115(6) 0.9560(4) 0.7153(4) 0.0471(12) Uani 1 1 d . . . . .
H15A H -0.077760 0.916867 0.719067 0.071 Uiso 1 1 calc R U . . .
H15B H -0.015048 1.041308 0.682450 0.071 Uiso 1 1 calc R U . . .
H15C H 0.044993 0.962539 0.791678 0.071 Uiso 1 1 calc R U . . .
C16 C 0.1382(4) 0.8746(3) 0.6421(3) 0.0269(8) Uani 1 1 d . . . . .
C17 C 0.2200(4) 0.9341(3) 0.5606(3) 0.0310(9) Uani 1 1 d . . . . .
H17 H 0.200052 1.024584 0.559211 0.037 Uiso 1 1 calc R U . . .
C18 C 0.3284(4) 0.8679(3) 0.4819(3) 0.0240(7) Uani 1 1 d . . . . .
C19 C 0.3999(5) 0.9396(4) 0.3914(4) 0.0372(10) Uani 1 1 d . . . . .
H19A H 0.510730 0.917397 0.393848 0.056 Uiso 1 1 calc R U . . .
H19B H 0.364355 1.031423 0.404148 0.056 Uiso 1 1 calc R U . . .
H19C H 0.371295 0.916720 0.317028 0.056 Uiso 1 1 calc R U . . .
C20 C 0.5311(4) 0.3447(4) 0.8089(3) 0.0313(8) Uani 1 1 d . . . . .
H20A H 0.558749 0.413340 0.853316 0.038 Uiso 1 1 calc R U . . .
H20B H 0.619528 0.272290 0.802996 0.038 Uiso 1 1 calc R U . . .
C21 C 0.3992(6) 0.3030(5) 0.8678(4) 0.0575(14) Uani 1 1 d . . . . .
H21A H 0.311871 0.374864 0.873750 0.086 Uiso 1 1 calc R U . . .
H21B H 0.425298 0.272760 0.943752 0.086 Uiso 1 1 calc R U . . .
H21C H 0.373471 0.233707 0.824579 0.086 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
Dy1 Dy1 3.9108(14) 2_666 ?
Dy1 O1 2.346(2) . ?
Dy1 O1 2.370(2) 2_666 ?
Dy1 O2 2.196(3) 2_666 ?
Dy1 O4 2.330(2) . ?
Dy1 O5 2.373(2) . ?
Dy1 O6 2.387(2) . ?
Dy1 N1 2.518(3) . ?
Dy1 N3 2.451(3) 2_666 ?
O1 C6 1.301(4) . ?
O2 C13 1.298(4) . ?
O3 C12 1.369(5) . ?
O3 C14 1.415(5) . ?
O4 C16 1.250(4) . ?
O5 C18 1.284(4) . ?
O6 H6 0.9500 . ?
O6 C20 1.445(4) . ?
N1 C1 1.333(4) . ?
N1 C5 1.354(4) . ?
N2 N3 1.414(4) . ?
N2 C6 1.308(4) . ?
N3 C7 1.294(5) . ?
C1 H1 0.9500 . ?
C1 C2 1.385(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.378(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.375(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.391(4) . ?
C5 C6 1.483(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.450(5) . ?
C8 C9 1.413(5) . ?
C8 C13 1.421(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.377(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.379(5) . ?
C12 C13 1.421(5) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C15 C16 1.512(5) . ?
C16 C17 1.405(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.389(5) . ?
C18 C19 1.502(5) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.485(6) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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 Dy1 Dy1 34.19(5) . 2_666 ?
O1 Dy1 Dy1 33.79(6) 2_666 2_666 ?
O1 Dy1 O1 67.97(9) . 2_666 ?
O1 Dy1 O5 73.00(8) 2_666 . ?
O1 Dy1 O5 82.79(8) . . ?
O1 Dy1 O6 75.52(9) 2_666 . ?
O1 Dy1 O6 76.27(9) . . ?
O1 Dy1 N1 65.13(9) . . ?
O1 Dy1 N1 130.65(8) 2_666 . ?
O1 Dy1 N3 63.99(9) 2_666 2_666 ?
O1 Dy1 N3 131.49(9) . 2_666 ?
O2 Dy1 Dy1 144.46(7) 2_666 2_666 ?
O2 Dy1 O1 144.26(8) 2_666 . ?
O2 Dy1 O1 122.63(9) 2_666 2_666 ?
O2 Dy1 O4 75.45(10) 2_666 . ?
O2 Dy1 O5 132.23(8) 2_666 . ?
O2 Dy1 O6 74.54(9) 2_666 . ?
O2 Dy1 N1 89.43(10) 2_666 . ?
O2 Dy1 N3 72.98(10) 2_666 2_666 ?
O4 Dy1 Dy1 140.08(7) . 2_666 ?
O4 Dy1 O1 141.69(8) . 2_666 ?
O4 Dy1 O1 119.06(9) . . ?
O4 Dy1 O5 70.97(9) . . ?
O4 Dy1 O6 141.89(9) . . ?
O4 Dy1 N1 77.38(9) . . ?
O4 Dy1 N3 95.53(9) . 2_666 ?
O5 Dy1 Dy1 75.38(6) . 2_666 ?
O5 Dy1 O6 146.95(9) . . ?
O5 Dy1 N1 114.50(9) . . ?
O5 Dy1 N3 77.47(9) . 2_666 ?
O6 Dy1 Dy1 72.91(7) . 2_666 ?
O6 Dy1 N1 79.36(9) . . ?
O6 Dy1 N3 97.61(10) . 2_666 ?
N1 Dy1 Dy1 98.20(7) . 2_666 ?
N3 Dy1 Dy1 97.56(7) 2_666 2_666 ?
N3 Dy1 N1 162.26(10) 2_666 . ?
Dy1 O1 Dy1 112.03(9) . 2_666 ?
C6 O1 Dy1 125.3(2) . . ?
C6 O1 Dy1 118.3(2) . 2_666 ?
C13 O2 Dy1 126.7(2) . 2_666 ?
C12 O3 C14 118.0(3) . . ?
C16 O4 Dy1 133.0(2) . . ?
C18 O5 Dy1 130.8(2) . . ?
Dy1 O6 H6 113.3 . . ?
C20 O6 Dy1 133.5(2) . . ?
C20 O6 H6 113.3 . . ?
C1 N1 Dy1 123.4(2) . . ?
C1 N1 C5 118.5(3) . . ?
C5 N1 Dy1 118.0(2) . . ?
C6 N2 N3 109.6(2) . . ?
N2 N3 Dy1 119.1(2) . 2_666 ?
C7 N3 Dy1 126.4(2) . 2_666 ?
C7 N3 N2 114.0(3) . . ?
N1 C1 H1 118.6 . . ?
N1 C1 C2 122.7(4) . . ?
C2 C1 H1 118.6 . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.4(3) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.9(3) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.7 . . ?
C3 C4 C5 118.7(3) . . ?
C5 C4 H4 120.7 . . ?
N1 C5 C4 121.8(3) . . ?
N1 C5 C6 114.6(3) . . ?
C4 C5 C6 123.6(3) . . ?
O1 C6 N2 125.6(3) . . ?
O1 C6 C5 116.2(3) . . ?
N2 C6 C5 118.2(3) . . ?
N3 C7 H7 118.1 . . ?
N3 C7 C8 123.8(3) . . ?
C8 C7 H7 118.1 . . ?
C9 C8 C7 117.3(3) . . ?
C9 C8 C13 120.2(3) . . ?
C13 C8 C7 122.5(3) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.4(4) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.2(4) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.4(4) . . ?
C12 C11 H11 119.8 . . ?
O3 C12 C11 124.7(4) . . ?
O3 C12 C13 113.8(3) . . ?
C11 C12 C13 121.5(4) . . ?
O2 C13 C8 122.9(3) . . ?
O2 C13 C12 119.9(3) . . ?
C12 C13 C8 117.2(3) . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C16 C15 H15C 109.5 . . ?
O4 C16 C15 116.7(4) . . ?
O4 C16 C17 124.4(3) . . ?
C17 C16 C15 118.9(3) . . ?
C16 C17 H17 118.2 . . ?
C18 C17 C16 123.6(3) . . ?
C18 C17 H17 118.2 . . ?
O5 C18 C17 123.9(3) . . ?
O5 C18 C19 116.3(3) . . ?
C17 C18 C19 119.8(3) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O6 C20 H20A 109.6 . . ?
O6 C20 H20B 109.6 . . ?
O6 C20 C21 110.2(3) . . ?
H20A C20 H20B 108.1 . . ?
C21 C20 H20A 109.6 . . ?
C21 C20 H20B 109.6 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
Dy1 O1 C6 N2 -15.8(4) 2_666 . . . ?
Dy1 O1 C6 N2 -170.4(3) . . . . ?
Dy1 O1 C6 C5 9.6(4) . . . . ?
Dy1 O1 C6 C5 164.2(2) 2_666 . . . ?
Dy1 O2 C13 C8 50.0(5) 2_666 . . . ?
Dy1 O2 C13 C12 -128.6(3) 2_666 . . . ?
Dy1 O4 C16 C15 -155.3(3) . . . . ?
Dy1 O4 C16 C17 25.6(6) . . . . ?
Dy1 O5 C18 C17 -26.6(5) . . . . ?
Dy1 O5 C18 C19 154.7(3) . . . . ?
Dy1 O6 C20 C21 86.0(4) . . . . ?
Dy1 N1 C1 C2 -178.2(3) . . . . ?
Dy1 N1 C5 C4 177.9(3) . . . . ?
Dy1 N1 C5 C6 -3.4(4) . . . . ?
Dy1 N3 C7 C8 -8.3(5) 2_666 . . . ?
O3 C12 C13 O2 0.0(5) . . . . ?
O3 C12 C13 C8 -178.7(3) . . . . ?
O4 C16 C17 C18 5.4(6) . . . . ?
N1 C1 C2 C3 0.3(6) . . . . ?
N1 C5 C6 O1 -3.3(4) . . . . ?
N1 C5 C6 N2 176.6(3) . . . . ?
N2 N3 C7 C8 -179.7(3) . . . . ?
N3 N2 C6 O1 1.2(5) . . . . ?
N3 N2 C6 C5 -178.8(3) . . . . ?
N3 C7 C8 C9 162.3(4) . . . . ?
N3 C7 C8 C13 -18.8(6) . . . . ?
C1 N1 C5 C4 -0.3(5) . . . . ?
C1 N1 C5 C6 178.4(3) . . . . ?
C1 C2 C3 C4 -0.2(6) . . . . ?
C2 C3 C4 C5 -0.2(6) . . . . ?
C3 C4 C5 N1 0.5(5) . . . . ?
C3 C4 C5 C6 -178.1(3) . . . . ?
C4 C5 C6 O1 175.3(3) . . . . ?
C4 C5 C6 N2 -4.7(5) . . . . ?
C5 N1 C1 C2 -0.1(6) . . . . ?
C6 N2 N3 Dy1 13.6(3) . . . 2_666 ?
C6 N2 N3 C7 -174.4(3) . . . . ?
C7 C8 C9 C10 -178.8(4) . . . . ?
C7 C8 C13 O2 0.1(6) . . . . ?
C7 C8 C13 C12 178.8(3) . . . . ?
C8 C9 C10 C11 -0.9(7) . . . . ?
C9 C8 C13 O2 179.0(3) . . . . ?
C9 C8 C13 C12 -2.4(5) . . . . ?
C9 C10 C11 C12 -0.3(7) . . . . ?
C10 C11 C12 O3 -179.9(4) . . . . ?
C10 C11 C12 C13 0.1(6) . . . . ?
C11 C12 C13 O2 179.9(4) . . . . ?
C11 C12 C13 C8 1.2(6) . . . . ?
C13 C8 C9 C10 2.3(6) . . . . ?
C14 O3 C12 C11 -19.6(6) . . . . ?
C14 O3 C12 C13 160.3(4) . . . . ?
C15 C16 C17 C18 -173.6(4) . . . . ?
C16 C17 C18 O5 -4.1(6) . . . . ?
C16 C17 C18 C19 174.5(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_shelxl_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1945854'
loop_
_audit_author_name
_audit_author_address
'XueMei Zhang'
;Tianjin University
China
;
_audit_update_record             
;
2020-10-06 deposited with the CCDC.	2020-10-09 downloaded from the CCDC.
;
_audit_creation_date             2020-09-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H20 N3 O6 Yb, C3 H8 O'
_chemical_formula_sum            'C22 H28 N3 O7 Yb'
_chemical_formula_weight         619.51
_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'
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      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                   11.316(2)
_cell_length_b                   14.635(3)
_cell_length_c                   15.540(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.14(3)
_cell_angle_gamma                90
_cell_volume                     2416.4(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7013
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9103
_cell_measurement_theta_min      2.3689
_shelx_estimated_absorpt_T_max   0.651
_shelx_estimated_absorpt_T_min   0.508
_exptl_absorpt_coefficient_mu    3.916
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.8350
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.703
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1228
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23756
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.866
_diffrn_reflns_theta_min         2.369
_diffrn_ambient_temperature      113.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'rigaku saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4946
_reflns_number_total             5742
_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       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         1.595
_refine_diff_density_min         -1.758
_refine_diff_density_rms         0.157
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         5742
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0309
_refine_ls_restrained_S_all      1.117
_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)+(0.0366P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0686
_refine_ls_wR_factor_ref         0.0719
_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, All O(H) groups, All O(H,H) groups
2.a Riding coordinates:
 O6(H6A,H6B), O7(H7A)
2.b Ternary CH refined with riding coordinates:
 C21(H21)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C9(H9), C10(H10), C11(H11), C17(H17)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.65547(2) 0.43808(2) 0.07278(2) 0.01166(6) Uani 1 1 d . . . . .
O1 O 0.5640(2) 0.56969(14) -0.00560(16) 0.0142(5) Uani 1 1 d . . . . .
O2 O 0.8148(2) 0.45361(15) 0.20482(16) 0.0153(5) Uani 1 1 d . . . . .
O3 O 0.9574(2) 0.37942(18) 0.35902(18) 0.0258(6) Uani 1 1 d . . . . .
O4 O 0.6266(2) 0.40067(16) -0.07903(17) 0.0188(5) Uani 1 1 d . . . . .
O5 O 0.7936(2) 0.32431(16) 0.07413(16) 0.0184(5) Uani 1 1 d . . . . .
O6 O 0.5739(2) 0.50230(18) 0.17595(17) 0.0254(6) Uani 1 1 d . . . . .
H6A H 0.512726 0.539379 0.159564 0.038 Uiso 1 1 d R U . . .
H6B H 0.616986 0.510599 0.231664 0.038 Uiso 1 1 d R U . . .
N1 N 0.4391(3) 0.69717(18) -0.12070(19) 0.0154(6) Uani 1 1 d . . . . .
N2 N 0.7543(3) 0.61609(19) -0.01732(19) 0.0165(6) Uani 1 1 d . . . . .
N3 N 0.8009(3) 0.54435(18) 0.0469(2) 0.0145(6) Uani 1 1 d . . . . .
C1 C 0.3727(3) 0.7661(2) -0.1725(2) 0.0193(7) Uani 1 1 d . . . . .
H1 H 0.284123 0.767096 -0.186592 0.023 Uiso 1 1 calc R U . . .
C2 C 0.4277(3) 0.8357(2) -0.2065(3) 0.0230(8) Uani 1 1 d . . . . .
H2 H 0.377750 0.883298 -0.242787 0.028 Uiso 1 1 calc R U . . .
C3 C 0.5575(4) 0.8344(3) -0.1861(3) 0.0258(8) Uani 1 1 d . . . . .
H3 H 0.597851 0.881086 -0.208253 0.031 Uiso 1 1 calc R U . . .
C4 C 0.6265(3) 0.7640(2) -0.1332(2) 0.0216(8) Uani 1 1 d . . . . .
H4 H 0.715046 0.761056 -0.119343 0.026 Uiso 1 1 calc R U . . .
C5 C 0.5647(3) 0.6969(2) -0.1003(2) 0.0143(6) Uani 1 1 d . . . . .
C6 C 0.6329(3) 0.6220(2) -0.0378(2) 0.0137(6) Uani 1 1 d . . . . .
C7 C 0.9227(3) 0.5389(2) 0.0793(2) 0.0155(7) Uani 1 1 d . . . . .
H7 H 0.969195 0.574850 0.051254 0.019 Uiso 1 1 calc R U . . .
C8 C 0.9919(3) 0.4812(2) 0.1557(2) 0.0149(6) Uani 1 1 d . . . . .
C9 C 1.1219(3) 0.4688(2) 0.1733(2) 0.0180(7) Uani 1 1 d . . . . .
H9 H 1.158334 0.491816 0.130957 0.022 Uiso 1 1 calc R U . . .
C10 C 1.1966(3) 0.4239(2) 0.2508(3) 0.0237(8) Uani 1 1 d . . . . .
H10 H 1.283107 0.413691 0.260555 0.028 Uiso 1 1 calc R U . . .
C11 C 1.1442(3) 0.3932(2) 0.3155(2) 0.0217(7) Uani 1 1 d . . . . .
H11 H 1.196303 0.364680 0.370312 0.026 Uiso 1 1 calc R U . . .
C12 C 1.0167(3) 0.4044(2) 0.2995(2) 0.0184(7) Uani 1 1 d . . . . .
C13 C 0.9352(3) 0.4455(2) 0.2174(2) 0.0131(6) Uani 1 1 d . . . . .
C14 C 1.0341(4) 0.3457(3) 0.4467(3) 0.0345(10) Uani 1 1 d . . . . .
H14A H 1.074637 0.288626 0.438897 0.052 Uiso 1 1 calc R U . . .
H14B H 0.981620 0.334258 0.484234 0.052 Uiso 1 1 calc R U . . .
H14C H 1.098748 0.391031 0.477077 0.052 Uiso 1 1 calc R U . . .
C15 C 0.6379(4) 0.3577(3) -0.2228(2) 0.0280(9) Uani 1 1 d . . . . .
H15A H 0.557371 0.325091 -0.242928 0.042 Uiso 1 1 calc R U . . .
H15B H 0.696865 0.326729 -0.246779 0.042 Uiso 1 1 calc R U . . .
H15C H 0.624787 0.420594 -0.245810 0.042 Uiso 1 1 calc R U . . .
C16 C 0.6914(3) 0.3588(2) -0.1196(2) 0.0175(7) Uani 1 1 d . . . . .
C17 C 0.8035(3) 0.3134(2) -0.0747(2) 0.0200(7) Uani 1 1 d . . . . .
H17 H 0.851702 0.291976 -0.109992 0.024 Uiso 1 1 calc R U . . .
C18 C 0.8492(3) 0.2976(2) 0.0203(2) 0.0176(7) Uani 1 1 d . . . . .
C19 C 0.9696(4) 0.2447(3) 0.0625(3) 0.0307(9) Uani 1 1 d . . . . .
H19A H 1.032163 0.283513 0.106572 0.046 Uiso 1 1 calc R U . . .
H19B H 1.001613 0.225336 0.014256 0.046 Uiso 1 1 calc R U . . .
H19C H 0.953176 0.190721 0.094011 0.046 Uiso 1 1 calc R U . . .
O7 O 0.7683(2) 0.99663(19) 0.14672(18) 0.0272(6) Uani 1 1 d . . . . .
H7A H 0.709774 0.967047 0.156628 0.041 Uiso 1 1 d R U . . .
C20 C 0.8253(4) 0.8426(3) 0.1181(3) 0.0389(11) Uani 1 1 d . . . . .
H20A H 0.908409 0.847505 0.165939 0.058 Uiso 1 1 calc R U . . .
H20B H 0.830469 0.801729 0.069542 0.058 Uiso 1 1 calc R U . . .
H20C H 0.765004 0.817876 0.144617 0.058 Uiso 1 1 calc R U . . .
C21 C 0.7824(4) 0.9359(3) 0.0784(3) 0.0263(9) Uani 1 1 d . . . . .
H21 H 0.699215 0.929706 0.027991 0.032 Uiso 1 1 calc R U . . .
C22 C 0.8738(4) 0.9807(4) 0.0404(3) 0.0433(12) Uani 1 1 d . . . . .
H22A H 0.843054 1.041734 0.017494 0.065 Uiso 1 1 calc R U . . .
H22B H 0.881416 0.943581 -0.009940 0.065 Uiso 1 1 calc R U . . .
H22C H 0.956255 0.985852 0.088836 0.065 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
Yb1 Yb1 3.9117(12) 3_665 ?
Yb1 O1 2.323(2) . ?
Yb1 O1 2.342(2) 3_665 ?
Yb1 O2 2.228(2) . ?
Yb1 O4 2.333(2) . ?
Yb1 O5 2.279(2) . ?
Yb1 O6 2.307(2) . ?
Yb1 N1 2.483(3) 3_665 ?
Yb1 N3 2.397(3) . ?
Yb1 C6 3.156(3) . ?
Yb1 C13 3.191(3) . ?
O1 C6 1.309(4) . ?
O2 C13 1.313(4) . ?
O3 C12 1.367(4) . ?
O3 C14 1.428(4) . ?
O4 C16 1.276(4) . ?
O5 C18 1.268(4) . ?
O6 H6A 0.8471 . ?
O6 H6B 0.8434 . ?
N1 C1 1.347(4) . ?
N1 C5 1.346(4) . ?
N2 N3 1.419(4) . ?
N2 C6 1.302(4) . ?
N3 C7 1.297(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.389(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.392(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.380(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.400(4) . ?
C5 C6 1.492(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.448(5) . ?
C8 C9 1.412(4) . ?
C8 C13 1.424(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.378(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.403(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.387(5) . ?
C12 C13 1.424(5) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C15 C16 1.506(5) . ?
C16 C17 1.389(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.406(5) . ?
C18 C19 1.506(5) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O7 H7A 0.8484 . ?
O7 C21 1.435(4) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C20 C21 1.509(6) . ?
C21 H21 1.0000 . ?
C21 C22 1.505(5) . ?
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 Yb1 Yb1 33.18(5) . 3_665 ?
O1 Yb1 Yb1 32.87(5) 3_665 3_665 ?
O1 Yb1 O1 66.04(9) . 3_665 ?
O1 Yb1 O4 77.43(8) . . ?
O1 Yb1 N1 131.15(8) . 3_665 ?
O1 Yb1 N1 66.09(8) 3_665 3_665 ?
O1 Yb1 N3 65.27(9) . . ?
O1 Yb1 N3 129.84(8) 3_665 . ?
O1 Yb1 C6 85.65(8) 3_665 . ?
O1 Yb1 C6 21.48(8) . . ?
O1 Yb1 C13 163.33(8) 3_665 . ?
O1 Yb1 C13 119.73(8) . . ?
O2 Yb1 Yb1 140.07(6) . 3_665 ?
O2 Yb1 O1 118.13(8) . . ?
O2 Yb1 O1 144.40(8) . 3_665 ?
O2 Yb1 O4 137.93(8) . . ?
O2 Yb1 O5 74.39(9) . . ?
O2 Yb1 O6 73.08(9) . . ?
O2 Yb1 N1 95.78(9) . 3_665 ?
O2 Yb1 N3 72.76(9) . . ?
O2 Yb1 C6 107.62(8) . . ?
O2 Yb1 C13 19.27(8) . . ?
O4 Yb1 Yb1 74.88(6) . 3_665 ?
O4 Yb1 O1 77.30(9) . 3_665 ?
O4 Yb1 N1 101.04(9) . 3_665 ?
O4 Yb1 N3 81.24(9) . . ?
O4 Yb1 C6 72.09(8) . . ?
O4 Yb1 C13 118.68(9) . . ?
O5 Yb1 Yb1 145.23(6) . 3_665 ?
O5 Yb1 O1 142.27(8) . . ?
O5 Yb1 O1 125.98(8) . 3_665 ?
O5 Yb1 O4 72.21(9) . . ?
O5 Yb1 O6 136.75(9) . . ?
O5 Yb1 N1 77.29(9) . 3_665 ?
O5 Yb1 N3 88.11(9) . . ?
O5 Yb1 C6 123.68(8) . . ?
O5 Yb1 C13 60.50(8) . . ?
O6 Yb1 Yb1 73.61(7) . 3_665 ?
O6 Yb1 O1 73.33(9) . 3_665 ?
O6 Yb1 O1 79.29(9) . . ?
O6 Yb1 O4 148.01(9) . . ?
O6 Yb1 N1 78.44(9) . 3_665 ?
O6 Yb1 N3 108.31(10) . . ?
O6 Yb1 C6 93.12(9) . . ?
O6 Yb1 C13 91.92(9) . . ?
N1 Yb1 Yb1 98.51(7) 3_665 3_665 ?
N1 Yb1 C6 151.72(9) 3_665 . ?
N1 Yb1 C13 103.96(9) 3_665 . ?
N3 Yb1 Yb1 97.77(7) . 3_665 ?
N3 Yb1 N1 163.58(9) . 3_665 ?
N3 Yb1 C6 44.50(9) . . ?
N3 Yb1 C13 61.60(9) . . ?
C6 Yb1 Yb1 53.27(6) . 3_665 ?
C6 Yb1 C13 103.26(8) . . ?
C13 Yb1 Yb1 150.24(5) . 3_665 ?
Yb1 O1 Yb1 113.95(9) . 3_665 ?
C6 O1 Yb1 122.5(2) . 3_665 ?
C6 O1 Yb1 118.0(2) . . ?
C13 O2 Yb1 126.7(2) . . ?
C12 O3 C14 117.4(3) . . ?
C16 O4 Yb1 135.1(2) . . ?
C18 O5 Yb1 135.5(2) . . ?
Yb1 O6 H6A 122.2 . . ?
Yb1 O6 H6B 123.0 . . ?
H6A O6 H6B 109.9 . . ?
C1 N1 Yb1 124.6(2) . 3_665 ?
C5 N1 Yb1 117.2(2) . 3_665 ?
C5 N1 C1 118.0(3) . . ?
C6 N2 N3 109.0(3) . . ?
N2 N3 Yb1 119.22(19) . . ?
C7 N3 Yb1 126.5(2) . . ?
C7 N3 N2 114.0(3) . . ?
N1 C1 H1 118.4 . . ?
N1 C1 C2 123.1(3) . . ?
C2 C1 H1 118.4 . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.6(3) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 120.6 . . ?
C4 C3 C2 118.9(3) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.3(3) . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 122.1(3) . . ?
N1 C5 C6 115.0(3) . . ?
C4 C5 C6 122.8(3) . . ?
O1 C6 Yb1 40.55(14) . . ?
O1 C6 C5 115.9(3) . . ?
N2 C6 Yb1 85.97(19) . . ?
N2 C6 O1 125.8(3) . . ?
N2 C6 C5 118.3(3) . . ?
C5 C6 Yb1 155.3(2) . . ?
N3 C7 H7 118.1 . . ?
N3 C7 C8 123.9(3) . . ?
C8 C7 H7 118.1 . . ?
C9 C8 C7 117.8(3) . . ?
C9 C8 C13 120.3(3) . . ?
C13 C8 C7 121.6(3) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 120.9(3) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.7(3) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.2(3) . . ?
C12 C11 H11 119.9 . . ?
O3 C12 C11 124.7(3) . . ?
O3 C12 C13 113.7(3) . . ?
C11 C12 C13 121.6(3) . . ?
O2 C13 Yb1 34.05(15) . . ?
O2 C13 C8 123.5(3) . . ?
O2 C13 C12 119.4(3) . . ?
C8 C13 Yb1 96.1(2) . . ?
C12 C13 Yb1 142.8(2) . . ?
C12 C13 C8 117.0(3) . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C16 C15 H15C 109.5 . . ?
O4 C16 C15 116.3(3) . . ?
O4 C16 C17 124.2(3) . . ?
C17 C16 C15 119.5(3) . . ?
C16 C17 H17 118.4 . . ?
C16 C17 C18 123.3(3) . . ?
C18 C17 H17 118.4 . . ?
O5 C18 C17 123.7(3) . . ?
O5 C18 C19 116.8(3) . . ?
C17 C18 C19 119.5(3) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 O7 H7A 96.4 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
C21 C20 H20C 109.5 . . ?
O7 C21 C20 111.1(3) . . ?
O7 C21 H21 108.7 . . ?
O7 C21 C22 106.7(3) . . ?
C20 C21 H21 108.7 . . ?
C22 C21 C20 112.7(4) . . ?
C22 C21 H21 108.7 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 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
Yb1 O1 C6 Yb1 -152.1(3) 3_665 . . . ?
Yb1 O1 C6 N2 -12.4(4) . . . . ?
Yb1 O1 C6 N2 -164.5(3) 3_665 . . . ?
Yb1 O1 C6 C5 170.4(2) . . . . ?
Yb1 O1 C6 C5 18.3(4) 3_665 . . . ?
Yb1 O2 C13 C8 41.3(4) . . . . ?
Yb1 O2 C13 C12 -142.9(3) . . . . ?
Yb1 O4 C16 C15 -174.9(2) . . . . ?
Yb1 O4 C16 C17 6.9(5) . . . . ?
Yb1 O5 C18 C17 -24.9(5) . . . . ?
Yb1 O5 C18 C19 156.2(3) . . . . ?
Yb1 N1 C1 C2 -172.8(3) 3_665 . . . ?
Yb1 N1 C5 C4 172.2(3) 3_665 . . . ?
Yb1 N1 C5 C6 -9.7(4) 3_665 . . . ?
Yb1 N3 C7 C8 -17.2(5) . . . . ?
O3 C12 C13 Yb1 -35.6(5) . . . . ?
O3 C12 C13 O2 -1.7(5) . . . . ?
O3 C12 C13 C8 174.3(3) . . . . ?
O4 C16 C17 C18 9.2(5) . . . . ?
N1 C1 C2 C3 0.1(6) . . . . ?
N1 C5 C6 Yb1 10.6(7) . . . . ?
N1 C5 C6 O1 -4.5(4) . . . . ?
N1 C5 C6 N2 178.1(3) . . . . ?
N2 N3 C7 C8 169.9(3) . . . . ?
N3 N2 C6 Yb1 -8.8(2) . . . . ?
N3 N2 C6 O1 -0.8(5) . . . . ?
N3 N2 C6 C5 176.4(3) . . . . ?
N3 C7 C8 C9 168.6(3) . . . . ?
N3 C7 C8 C13 -17.9(5) . . . . ?
C1 N1 C5 C4 -1.8(5) . . . . ?
C1 N1 C5 C6 176.3(3) . . . . ?
C1 C2 C3 C4 0.1(6) . . . . ?
C2 C3 C4 C5 -1.1(6) . . . . ?
C3 C4 C5 N1 2.0(5) . . . . ?
C3 C4 C5 C6 -175.9(3) . . . . ?
C4 C5 C6 Yb1 -171.4(4) . . . . ?
C4 C5 C6 O1 173.5(3) . . . . ?
C4 C5 C6 N2 -3.9(5) . . . . ?
C5 N1 C1 C2 0.7(5) . . . . ?
C6 N2 N3 Yb1 13.4(3) . . . . ?
C6 N2 N3 C7 -173.1(3) . . . . ?
C7 C8 C9 C10 172.3(3) . . . . ?
C7 C8 C13 Yb1 29.3(3) . . . . ?
C7 C8 C13 O2 7.5(5) . . . . ?
C7 C8 C13 C12 -168.4(3) . . . . ?
C8 C9 C10 C11 -2.7(6) . . . . ?
C9 C8 C13 Yb1 -157.4(3) . . . . ?
C9 C8 C13 O2 -179.2(3) . . . . ?
C9 C8 C13 C12 4.9(5) . . . . ?
C9 C10 C11 C12 2.8(6) . . . . ?
C10 C11 C12 O3 -178.0(3) . . . . ?
C10 C11 C12 C13 1.0(5) . . . . ?
C11 C12 C13 Yb1 145.2(3) . . . . ?
C11 C12 C13 O2 179.1(3) . . . . ?
C11 C12 C13 C8 -4.8(5) . . . . ?
C13 C8 C9 C10 -1.3(5) . . . . ?
C14 O3 C12 C11 5.0(5) . . . . ?
C14 O3 C12 C13 -174.2(3) . . . . ?
C15 C16 C17 C18 -168.9(3) . . . . ?
C16 C17 C18 O5 -1.1(5) . . . . ?
C16 C17 C18 C19 177.8(3) . . . . ?

_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_shelxl_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1947934'
loop_
_audit_author_name
_audit_author_address
'XueMei Zhang'
;Tianjin University
China
;
_audit_update_record             
;
2020-10-06 deposited with the CCDC.	2020-10-09 downloaded from the CCDC.
;
_audit_creation_date             2020-09-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H20 Ho N3 O6, C3 H8 O'
_chemical_formula_sum            'C22 H28 Ho N3 O7'
_chemical_formula_weight         611.40
_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'
Ho Ho -0.2175 4.6783 '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                   11.304(2)
_cell_length_b                   14.712(3)
_cell_length_c                   15.521(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.03(3)
_cell_angle_gamma                90
_cell_volume                     2425.0(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7081
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.8984
_cell_measurement_theta_min      1.9477
_shelx_estimated_absorpt_T_max   0.733
_shelx_estimated_absorpt_T_min   0.587
_exptl_absorpt_coefficient_mu    3.308
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.7362
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.675
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23830
_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         27.840
_diffrn_reflns_theta_min         1.966
_diffrn_ambient_temperature      113.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4933
_reflns_number_total             5761
_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       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         1.376
_refine_diff_density_min         -1.808
_refine_diff_density_rms         0.148
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         5761
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0310
_refine_ls_restrained_S_all      1.075
_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)+(0.0363P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0683
_refine_ls_wR_factor_ref         0.0718
_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, All O(H) groups, All O(H,H) groups
2.a Riding coordinates:
 O6(H6A,H6B), O7(H7A)
2.b Ternary CH refined with riding coordinates:
 C21(H21)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C9(H9), C10(H10), C11(H11), C17(H17)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
Ho1 Ho 0.65602(2) 0.43772(2) 0.07319(2) 0.01168(6) Uani 1 1 d . . . . .
O1 O 0.5657(2) 0.57024(12) -0.00598(14) 0.0136(4) Uani 1 1 d . . . . .
O2 O 0.8168(2) 0.45502(14) 0.20621(14) 0.0149(4) Uani 1 1 d . . . . .
O3 O 0.9598(2) 0.38072(16) 0.35922(15) 0.0248(5) Uani 1 1 d . . . . .
O4 O 0.6283(2) 0.40011(15) -0.08029(15) 0.0182(5) Uani 1 1 d . . . . .
O5 O 0.7958(2) 0.32338(14) 0.07353(14) 0.0186(5) Uani 1 1 d . . . . .
O6 O 0.5708(2) 0.50107(16) 0.17797(15) 0.0258(5) Uani 1 1 d . . . . .
H6A H 0.509629 0.538142 0.161576 0.039 Uiso 1 1 d R U . . .
H6B H 0.613889 0.509362 0.233676 0.039 Uiso 1 1 d R U . . .
N1 N 0.4423(2) 0.69887(16) -0.11974(17) 0.0154(5) Uani 1 1 d . . . . .
N2 N 0.7566(2) 0.61757(17) -0.01605(17) 0.0167(5) Uani 1 1 d . . . . .
N3 N 0.8033(3) 0.54627(17) 0.04819(18) 0.0152(5) Uani 1 1 d . . . . .
C1 C 0.3759(3) 0.7675(2) -0.1713(2) 0.0185(7) Uani 1 1 d . . . . .
H1 H 0.287227 0.768951 -0.185489 0.022 Uiso 1 1 calc R U . . .
C2 C 0.4328(3) 0.8366(2) -0.2046(2) 0.0233(7) Uani 1 1 d . . . . .
H2 H 0.383822 0.884497 -0.240578 0.028 Uiso 1 1 calc R U . . .
C3 C 0.5616(3) 0.8343(2) -0.1846(2) 0.0252(8) Uani 1 1 d . . . . .
H3 H 0.602288 0.880377 -0.207112 0.030 Uiso 1 1 calc R U . . .
C4 C 0.6306(3) 0.7644(2) -0.1314(2) 0.0214(7) Uani 1 1 d . . . . .
H4 H 0.719330 0.761581 -0.116888 0.026 Uiso 1 1 calc R U . . .
C5 C 0.5681(3) 0.6981(2) -0.0996(2) 0.0139(6) Uani 1 1 d . . . . .
C6 C 0.6357(3) 0.62329(19) -0.0371(2) 0.0133(6) Uani 1 1 d . . . . .
C7 C 0.9242(3) 0.5407(2) 0.0799(2) 0.0155(6) Uani 1 1 d . . . . .
H7 H 0.970659 0.576821 0.051970 0.019 Uiso 1 1 calc R U . . .
C8 C 0.9935(3) 0.4828(2) 0.1558(2) 0.0144(6) Uani 1 1 d . . . . .
C9 C 1.1232(3) 0.4698(2) 0.1723(2) 0.0188(7) Uani 1 1 d . . . . .
H9 H 1.159176 0.492357 0.129422 0.023 Uiso 1 1 calc R U . . .
C10 C 1.1980(3) 0.4252(2) 0.2493(3) 0.0233(7) Uani 1 1 d . . . . .
H10 H 1.284576 0.415204 0.258718 0.028 Uiso 1 1 calc R U . . .
C11 C 1.1457(3) 0.3944(2) 0.3141(2) 0.0224(7) Uani 1 1 d . . . . .
H11 H 1.197844 0.365434 0.368554 0.027 Uiso 1 1 calc R U . . .
C12 C 1.0191(3) 0.4059(2) 0.2992(2) 0.0184(7) Uani 1 1 d . . . . .
C13 C 0.9364(3) 0.44748(19) 0.2174(2) 0.0139(6) Uani 1 1 d . . . . .
C14 C 1.0366(4) 0.3479(3) 0.4469(2) 0.0348(9) Uani 1 1 d . . . . .
H14A H 1.082499 0.293785 0.439242 0.052 Uiso 1 1 calc R U . . .
H14B H 0.983283 0.332247 0.483005 0.052 Uiso 1 1 calc R U . . .
H14C H 1.096733 0.395154 0.478903 0.052 Uiso 1 1 calc R U . . .
C15 C 0.6399(3) 0.3539(3) -0.2234(2) 0.0282(8) Uani 1 1 d . . . . .
H15A H 0.557166 0.324377 -0.243038 0.042 Uiso 1 1 calc R U . . .
H15B H 0.696783 0.319504 -0.246731 0.042 Uiso 1 1 calc R U . . .
H15C H 0.631099 0.416017 -0.247549 0.042 Uiso 1 1 calc R U . . .
C16 C 0.6929(3) 0.3566(2) -0.1205(2) 0.0186(7) Uani 1 1 d . . . . .
C17 C 0.8038(3) 0.3111(2) -0.0756(2) 0.0192(6) Uani 1 1 d . . . . .
H17 H 0.851067 0.288565 -0.111168 0.023 Uiso 1 1 calc R U . . .
C18 C 0.8508(3) 0.2963(2) 0.0197(2) 0.0179(6) Uani 1 1 d . . . . .
C19 C 0.9714(4) 0.2441(3) 0.0613(2) 0.0308(8) Uani 1 1 d . . . . .
H19A H 1.033515 0.282556 0.105907 0.046 Uiso 1 1 calc R U . . .
H19B H 1.003865 0.225820 0.012909 0.046 Uiso 1 1 calc R U . . .
H19C H 0.955255 0.189803 0.092218 0.046 Uiso 1 1 calc R U . . .
O7 O 0.7677(2) 0.99819(17) 0.14685(16) 0.0273(6) Uani 1 1 d . . . . .
H7A H 0.709221 0.968618 0.156760 0.041 Uiso 1 1 d R U . . .
C20 C 0.8231(4) 0.8447(3) 0.1192(3) 0.0389(10) Uani 1 1 d . . . . .
H20A H 0.905590 0.849652 0.167710 0.058 Uiso 1 1 calc R U . . .
H20B H 0.829204 0.803479 0.071299 0.058 Uiso 1 1 calc R U . . .
H20C H 0.761626 0.820763 0.145136 0.058 Uiso 1 1 calc R U . . .
C21 C 0.7817(4) 0.9366(2) 0.0787(3) 0.0277(8) Uani 1 1 d . . . . .
H21 H 0.698495 0.930381 0.028432 0.033 Uiso 1 1 calc R U . . .
C22 C 0.8734(4) 0.9804(3) 0.0401(3) 0.0436(11) Uani 1 1 d . . . . .
H22A H 0.843827 1.041560 0.017943 0.065 Uiso 1 1 calc R U . . .
H22B H 0.879460 0.943659 -0.010923 0.065 Uiso 1 1 calc R U . . .
H22C H 0.956420 0.984451 0.088044 0.065 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
Ho1 Ho1 3.9335(12) 3_665 ?
Ho1 O1 2.365(2) 3_665 ?
Ho1 O1 2.344(2) . ?
Ho1 O2 2.250(2) . ?
Ho1 O4 2.359(2) . ?
Ho1 O5 2.307(2) . ?
Ho1 O6 2.348(2) . ?
Ho1 N1 2.519(3) 3_665 ?
Ho1 N3 2.432(3) . ?
O1 C6 1.315(3) . ?
O2 C13 1.308(4) . ?
O3 C12 1.371(4) . ?
O3 C14 1.425(4) . ?
O4 C16 1.283(4) . ?
O5 C18 1.264(4) . ?
O6 H6A 0.8486 . ?
O6 H6B 0.8433 . ?
N1 C1 1.347(4) . ?
N1 C5 1.348(4) . ?
N2 N3 1.419(3) . ?
N2 C6 1.294(4) . ?
N3 C7 1.286(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.394(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.381(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.391(4) . ?
C5 C6 1.492(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.447(4) . ?
C8 C9 1.412(4) . ?
C8 C13 1.423(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.372(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.405(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.380(4) . ?
C12 C13 1.430(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C15 C16 1.502(4) . ?
C16 C17 1.380(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.407(4) . ?
C18 C19 1.504(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O7 H7A 0.8485 . ?
O7 C21 1.442(4) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C20 C21 1.497(5) . ?
C21 H21 1.0000 . ?
C21 C22 1.508(5) . ?
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 Ho1 Ho1 33.52(5) . 3_665 ?
O1 Ho1 Ho1 33.18(5) 3_665 3_665 ?
O1 Ho1 O1 66.70(8) . 3_665 ?
O1 Ho1 O4 77.43(8) . . ?
O1 Ho1 O6 79.90(8) . . ?
O1 Ho1 N1 131.17(8) . 3_665 ?
O1 Ho1 N1 65.30(7) 3_665 3_665 ?
O1 Ho1 N3 129.95(8) 3_665 . ?
O1 Ho1 N3 64.49(8) . . ?
O2 Ho1 Ho1 139.49(5) . 3_665 ?
O2 Ho1 O1 117.19(7) . . ?
O2 Ho1 O1 144.25(8) . 3_665 ?
O2 Ho1 O4 137.67(8) . . ?
O2 Ho1 O5 75.09(8) . . ?
O2 Ho1 O6 73.36(8) . . ?
O2 Ho1 N1 97.13(8) . 3_665 ?
O2 Ho1 N3 71.94(8) . . ?
O4 Ho1 Ho1 75.12(6) . 3_665 ?
O4 Ho1 O1 77.80(8) . 3_665 ?
O4 Ho1 N1 100.56(8) . 3_665 ?
O4 Ho1 N3 81.63(9) . . ?
O5 Ho1 Ho1 145.00(5) . 3_665 ?
O5 Ho1 O1 125.92(7) . 3_665 ?
O5 Ho1 O1 141.51(8) . . ?
O5 Ho1 O4 71.67(8) . . ?
O5 Ho1 O6 136.97(8) . . ?
O5 Ho1 N1 77.69(8) . 3_665 ?
O5 Ho1 N3 88.47(9) . . ?
O6 Ho1 Ho1 73.49(6) . 3_665 ?
O6 Ho1 O1 72.60(8) . 3_665 ?
O6 Ho1 O4 148.00(8) . . ?
O6 Ho1 N1 78.01(8) . 3_665 ?
O6 Ho1 N3 108.38(9) . . ?
N1 Ho1 Ho1 98.10(6) 3_665 3_665 ?
N3 Ho1 Ho1 97.44(6) . 3_665 ?
N3 Ho1 N1 164.34(9) . 3_665 ?
Ho1 O1 Ho1 113.30(8) . 3_665 ?
C6 O1 Ho1 123.18(18) . 3_665 ?
C6 O1 Ho1 118.52(19) . . ?
C13 O2 Ho1 125.89(19) . . ?
C12 O3 C14 117.5(3) . . ?
C16 O4 Ho1 135.0(2) . . ?
C18 O5 Ho1 136.0(2) . . ?
Ho1 O6 H6A 122.2 . . ?
Ho1 O6 H6B 122.5 . . ?
H6A O6 H6B 109.8 . . ?
C1 N1 Ho1 124.0(2) . 3_665 ?
C1 N1 C5 118.3(3) . . ?
C5 N1 Ho1 117.42(19) . 3_665 ?
C6 N2 N3 109.4(2) . . ?
N2 N3 Ho1 119.14(19) . . ?
C7 N3 Ho1 126.3(2) . . ?
C7 N3 N2 114.0(3) . . ?
N1 C1 H1 118.9 . . ?
N1 C1 C2 122.3(3) . . ?
C2 C1 H1 118.9 . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 118.9(3) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.3(3) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.9(3) . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 122.4(3) . . ?
N1 C5 C6 114.9(3) . . ?
C4 C5 C6 122.6(3) . . ?
O1 C6 C5 116.0(3) . . ?
N2 C6 O1 125.8(3) . . ?
N2 C6 C5 118.2(3) . . ?
N3 C7 H7 118.1 . . ?
N3 C7 C8 123.9(3) . . ?
C8 C7 H7 118.1 . . ?
C9 C8 C7 117.8(3) . . ?
C9 C8 C13 120.7(3) . . ?
C13 C8 C7 121.2(3) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.0(3) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.5(3) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.5(3) . . ?
C12 C11 H11 119.8 . . ?
O3 C12 C11 125.0(3) . . ?
O3 C12 C13 113.3(3) . . ?
C11 C12 C13 121.7(3) . . ?
O2 C13 C8 124.5(3) . . ?
O2 C13 C12 119.0(3) . . ?
C8 C13 C12 116.4(3) . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C16 C15 H15C 109.5 . . ?
O4 C16 C15 116.4(3) . . ?
O4 C16 C17 124.5(3) . . ?
C17 C16 C15 119.1(3) . . ?
C16 C17 H17 118.1 . . ?
C16 C17 C18 123.8(3) . . ?
C18 C17 H17 118.1 . . ?
O5 C18 C17 123.5(3) . . ?
O5 C18 C19 117.1(3) . . ?
C17 C18 C19 119.4(3) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 O7 H7A 95.7 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
C21 C20 H20C 109.5 . . ?
O7 C21 C20 110.9(3) . . ?
O7 C21 H21 108.7 . . ?
O7 C21 C22 106.6(3) . . ?
C20 C21 H21 108.7 . . ?
C20 C21 C22 113.2(4) . . ?
C22 C21 H21 108.7 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 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
Ho1 O1 C6 N2 -11.7(4) . . . . ?
Ho1 O1 C6 N2 -165.0(2) 3_665 . . . ?
Ho1 O1 C6 C5 170.41(18) . . . . ?
Ho1 O1 C6 C5 17.1(3) 3_665 . . . ?
Ho1 O2 C13 C8 41.9(4) . . . . ?
Ho1 O2 C13 C12 -142.0(2) . . . . ?
Ho1 O4 C16 C15 -176.6(2) . . . . ?
Ho1 O4 C16 C17 5.3(5) . . . . ?
Ho1 O5 C18 C17 -25.1(5) . . . . ?
Ho1 O5 C18 C19 156.1(2) . . . . ?
Ho1 N1 C1 C2 -172.3(2) 3_665 . . . ?
Ho1 N1 C5 C4 172.1(2) 3_665 . . . ?
Ho1 N1 C5 C6 -10.6(3) 3_665 . . . ?
Ho1 N3 C7 C8 -17.8(4) . . . . ?
O3 C12 C13 O2 -2.0(4) . . . . ?
O3 C12 C13 C8 174.4(3) . . . . ?
O4 C16 C17 C18 9.1(5) . . . . ?
N1 C1 C2 C3 0.4(5) . . . . ?
N1 C5 C6 O1 -3.1(4) . . . . ?
N1 C5 C6 N2 178.9(3) . . . . ?
N2 N3 C7 C8 170.4(3) . . . . ?
N3 N2 C6 O1 -1.6(4) . . . . ?
N3 N2 C6 C5 176.2(2) . . . . ?
N3 C7 C8 C9 168.0(3) . . . . ?
N3 C7 C8 C13 -18.2(5) . . . . ?
C1 N1 C5 C4 -1.2(4) . . . . ?
C1 N1 C5 C6 176.1(3) . . . . ?
C1 C2 C3 C4 -0.6(5) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
C3 C4 C5 N1 0.9(5) . . . . ?
C3 C4 C5 C6 -176.1(3) . . . . ?
C4 C5 C6 O1 174.2(3) . . . . ?
C4 C5 C6 N2 -3.9(4) . . . . ?
C5 N1 C1 C2 0.5(5) . . . . ?
C6 N2 N3 Ho1 13.8(3) . . . . ?
C6 N2 N3 C7 -173.8(3) . . . . ?
C7 C8 C9 C10 171.9(3) . . . . ?
C7 C8 C13 O2 7.8(5) . . . . ?
C7 C8 C13 C12 -168.5(3) . . . . ?
C8 C9 C10 C11 -2.0(5) . . . . ?
C9 C8 C13 O2 -178.6(3) . . . . ?
C9 C8 C13 C12 5.1(4) . . . . ?
C9 C10 C11 C12 2.3(5) . . . . ?
C10 C11 C12 O3 -178.0(3) . . . . ?
C10 C11 C12 C13 1.2(5) . . . . ?
C11 C12 C13 O2 178.7(3) . . . . ?
C11 C12 C13 C8 -4.8(5) . . . . ?
C13 C8 C9 C10 -1.9(5) . . . . ?
C14 O3 C12 C11 6.0(5) . . . . ?
C14 O3 C12 C13 -173.2(3) . . . . ?
C15 C16 C17 C18 -169.0(3) . . . . ?
C16 C17 C18 O5 -0.1(5) . . . . ?
C16 C17 C18 C19 178.7(3) . . . . ?

_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_shelxl_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1945857'
loop_
_audit_author_name
_audit_author_address
'XueMei Zhang'
;Tianjin University
China
;
_audit_update_record             
;
2020-10-06 deposited with the CCDC.	2020-10-09 downloaded from the CCDC.
;
_audit_creation_date             2020-09-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H20 Er N3 O6, C3 H8 O'
_chemical_formula_sum            'C22 H28 Er N3 O7'
_chemical_formula_weight         613.73
_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'
Er Er -0.2586 4.9576 '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                   11.312(2)
_cell_length_b                   14.684(3)
_cell_length_c                   15.527(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.12(3)
_cell_angle_gamma                90
_cell_volume                     2421.8(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6894
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.8984
_cell_measurement_theta_min      2.3665
_shelx_estimated_absorpt_T_max   0.639
_shelx_estimated_absorpt_T_min   0.499
_exptl_absorpt_coefficient_mu    3.511
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.8243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1220
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            28769
_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         27.883
_diffrn_reflns_theta_min         2.367
_diffrn_ambient_temperature      113.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5041
_reflns_number_total             5781
_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       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         1.194
_refine_diff_density_min         -1.645
_refine_diff_density_rms         0.151
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         5781
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0307
_refine_ls_restrained_S_all      1.122
_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)+(0.0368P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0672
_refine_ls_wR_factor_ref         0.0701
_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, All O(H) groups, All O(H,H) groups
2.a Riding coordinates:
 O6(H6A,H6B), O7(H7A)
2.b Ternary CH refined with riding coordinates:
 C21(H21)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C9(H9), C10(H10), C11(H11), C17(H17)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
Er1 Er 0.65590(2) 0.43780(2) 0.07302(2) 0.01113(5) Uani 1 1 d . . . . .
O1 O 0.5654(2) 0.57021(12) -0.00569(15) 0.0133(4) Uani 1 1 d . . . . .
O2 O 0.8165(2) 0.45460(14) 0.20592(15) 0.0143(4) Uani 1 1 d . . . . .
O3 O 0.9590(2) 0.38031(16) 0.35925(16) 0.0247(5) Uani 1 1 d . . . . .
O4 O 0.6281(2) 0.40039(14) -0.07972(15) 0.0177(5) Uani 1 1 d . . . . .
O5 O 0.7950(2) 0.32355(14) 0.07387(15) 0.0170(5) Uani 1 1 d . . . . .
O6 O 0.5722(2) 0.50141(16) 0.17701(16) 0.0247(5) Uani 1 1 d . . . . .
H6A H 0.511042 0.538477 0.160623 0.037 Uiso 1 1 d R U . . .
H6B H 0.615302 0.509697 0.232723 0.037 Uiso 1 1 d R U . . .
N1 N 0.4412(2) 0.69825(16) -0.12001(18) 0.0157(5) Uani 1 1 d . . . . .
N2 N 0.7559(2) 0.61711(16) -0.01642(18) 0.0155(5) Uani 1 1 d . . . . .
N3 N 0.8023(2) 0.54538(16) 0.04747(18) 0.0136(5) Uani 1 1 d . . . . .
C1 C 0.3756(3) 0.7670(2) -0.1716(2) 0.0180(6) Uani 1 1 d . . . . .
H1 H 0.286921 0.768363 -0.185785 0.022 Uiso 1 1 calc R U . . .
C2 C 0.4312(3) 0.8362(2) -0.2050(2) 0.0226(7) Uani 1 1 d . . . . .
H2 H 0.381608 0.883904 -0.241035 0.027 Uiso 1 1 calc R U . . .
C3 C 0.5605(3) 0.8345(2) -0.1849(3) 0.0262(8) Uani 1 1 d . . . . .
H3 H 0.600929 0.880908 -0.207117 0.031 Uiso 1 1 calc R U . . .
C4 C 0.6293(3) 0.7644(2) -0.1322(2) 0.0216(7) Uani 1 1 d . . . . .
H4 H 0.717839 0.761412 -0.118204 0.026 Uiso 1 1 calc R U . . .
C5 C 0.5672(3) 0.6978(2) -0.0997(2) 0.0142(6) Uani 1 1 d . . . . .
C6 C 0.6342(3) 0.62283(19) -0.0373(2) 0.0125(6) Uani 1 1 d . . . . .
C7 C 0.9236(3) 0.5400(2) 0.0797(2) 0.0150(6) Uani 1 1 d . . . . .
H7 H 0.970095 0.576197 0.051880 0.018 Uiso 1 1 calc R U . . .
C8 C 0.9930(3) 0.48181(19) 0.1558(2) 0.0140(6) Uani 1 1 d . . . . .
C9 C 1.1224(3) 0.4695(2) 0.1725(2) 0.0176(6) Uani 1 1 d . . . . .
H9 H 1.158402 0.492383 0.129876 0.021 Uiso 1 1 calc R U . . .
C10 C 1.1971(3) 0.4246(2) 0.2496(3) 0.0228(7) Uani 1 1 d . . . . .
H10 H 1.283560 0.414310 0.258919 0.027 Uiso 1 1 calc R U . . .
C11 C 1.1451(3) 0.3941(2) 0.3148(2) 0.0212(7) Uani 1 1 d . . . . .
H11 H 1.197485 0.365669 0.369555 0.025 Uiso 1 1 calc R U . . .
C12 C 1.0182(3) 0.4052(2) 0.2994(2) 0.0174(6) Uani 1 1 d . . . . .
C13 C 0.9363(3) 0.44703(18) 0.2175(2) 0.0129(6) Uani 1 1 d . . . . .
C14 C 1.0360(3) 0.3474(3) 0.4466(3) 0.0321(9) Uani 1 1 d . . . . .
H14A H 1.078477 0.291440 0.438795 0.048 Uiso 1 1 calc R U . . .
H14B H 0.983576 0.334511 0.483928 0.048 Uiso 1 1 calc R U . . .
H14C H 1.099053 0.393506 0.477230 0.048 Uiso 1 1 calc R U . . .
C15 C 0.6397(3) 0.3555(3) -0.2233(2) 0.0265(8) Uani 1 1 d . . . . .
H15A H 0.557627 0.324987 -0.243525 0.040 Uiso 1 1 calc R U . . .
H15B H 0.697478 0.322269 -0.246740 0.040 Uiso 1 1 calc R U . . .
H15C H 0.629736 0.417966 -0.246845 0.040 Uiso 1 1 calc R U . . .
C16 C 0.6922(3) 0.3572(2) -0.1204(2) 0.0170(6) Uani 1 1 d . . . . .
C17 C 0.8043(3) 0.3120(2) -0.0750(2) 0.0179(6) Uani 1 1 d . . . . .
H17 H 0.852542 0.290273 -0.110140 0.021 Uiso 1 1 calc R U . . .
C18 C 0.8501(3) 0.2966(2) 0.0198(2) 0.0179(6) Uani 1 1 d . . . . .
C19 C 0.9702(3) 0.2444(2) 0.0616(3) 0.0283(8) Uani 1 1 d . . . . .
H19A H 1.032938 0.283442 0.105238 0.042 Uiso 1 1 calc R U . . .
H19B H 1.001833 0.224899 0.013154 0.042 Uiso 1 1 calc R U . . .
H19C H 0.954361 0.190847 0.093623 0.042 Uiso 1 1 calc R U . . .
O7 O 0.7683(2) 0.99776(17) 0.14687(16) 0.0259(5) Uani 1 1 d . . . . .
H7A H 0.709796 0.968188 0.156781 0.039 Uiso 1 1 d R U . . .
C20 C 0.8236(4) 0.8437(3) 0.1187(3) 0.0372(9) Uani 1 1 d . . . . .
H20A H 0.908647 0.847597 0.164140 0.056 Uiso 1 1 calc R U . . .
H20B H 0.823626 0.801807 0.069590 0.056 Uiso 1 1 calc R U . . .
H20C H 0.765403 0.821267 0.148263 0.056 Uiso 1 1 calc R U . . .
C21 C 0.7822(4) 0.9364(2) 0.0789(3) 0.0271(8) Uani 1 1 d . . . . .
H21 H 0.698912 0.930429 0.028605 0.032 Uiso 1 1 calc R U . . .
C22 C 0.8738(4) 0.9809(3) 0.0402(3) 0.0429(11) Uani 1 1 d . . . . .
H22A H 0.842597 1.041393 0.016532 0.064 Uiso 1 1 calc R U . . .
H22B H 0.881862 0.943284 -0.009581 0.064 Uiso 1 1 calc R U . . .
H22C H 0.956192 0.986732 0.088725 0.064 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
Er1 Er1 3.9264(12) 3_665 ?
Er1 O1 2.361(2) 3_665 ?
Er1 O1 2.337(2) . ?
Er1 O2 2.245(2) . ?
Er1 O4 2.348(2) . ?
Er1 O5 2.297(2) . ?
Er1 O6 2.330(2) . ?
Er1 N1 2.506(2) 3_665 ?
Er1 N3 2.418(3) . ?
O1 C6 1.305(3) . ?
O2 C13 1.309(4) . ?
O3 C12 1.369(4) . ?
O3 C14 1.421(4) . ?
O4 C16 1.281(4) . ?
O5 C18 1.268(4) . ?
O6 H6A 0.8479 . ?
O6 H6B 0.8429 . ?
N1 C1 1.343(4) . ?
N1 C5 1.350(4) . ?
N2 N3 1.418(3) . ?
N2 C6 1.304(4) . ?
N3 C7 1.290(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.386(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.377(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.396(4) . ?
C5 C6 1.490(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.451(4) . ?
C8 C9 1.407(4) . ?
C8 C13 1.419(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.373(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.408(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.381(4) . ?
C12 C13 1.430(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C15 C16 1.501(4) . ?
C16 C17 1.390(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.400(4) . ?
C18 C19 1.499(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O7 H7A 0.8487 . ?
O7 C21 1.436(4) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C20 C21 1.502(5) . ?
C21 H21 1.0000 . ?
C21 C22 1.512(5) . ?
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 Er1 Er1 33.50(5) . 3_665 ?
O1 Er1 Er1 33.11(5) 3_665 3_665 ?
O1 Er1 O1 66.61(8) . 3_665 ?
O1 Er1 O4 77.53(8) . . ?
O1 Er1 N1 131.19(8) . 3_665 ?
O1 Er1 N1 65.48(7) 3_665 3_665 ?
O1 Er1 N3 129.92(8) 3_665 . ?
O1 Er1 N3 64.67(8) . . ?
O2 Er1 Er1 139.62(5) . 3_665 ?
O2 Er1 O1 117.36(7) . . ?
O2 Er1 O1 144.28(8) . 3_665 ?
O2 Er1 O4 137.65(8) . . ?
O2 Er1 O5 74.86(8) . . ?
O2 Er1 O6 73.26(8) . . ?
O2 Er1 N1 96.72(8) . 3_665 ?
O2 Er1 N3 72.29(8) . . ?
O4 Er1 Er1 75.17(6) . 3_665 ?
O4 Er1 O1 77.76(8) . 3_665 ?
O4 Er1 N1 100.82(8) . 3_665 ?
O4 Er1 N3 81.28(9) . . ?
O5 Er1 Er1 145.15(5) . 3_665 ?
O5 Er1 O1 125.89(7) . 3_665 ?
O5 Er1 O1 141.86(8) . . ?
O5 Er1 O4 71.84(8) . . ?
O5 Er1 O6 136.86(8) . . ?
O5 Er1 N1 77.54(8) . 3_665 ?
O5 Er1 N3 88.36(8) . . ?
O6 Er1 Er1 73.46(6) . 3_665 ?
O6 Er1 O1 79.61(8) . . ?
O6 Er1 O1 72.85(8) . 3_665 ?
O6 Er1 O4 148.09(8) . . ?
O6 Er1 N1 78.14(8) . 3_665 ?
O6 Er1 N3 108.44(9) . . ?
N1 Er1 Er1 98.18(6) 3_665 3_665 ?
N3 Er1 Er1 97.54(6) . 3_665 ?
N3 Er1 N1 164.14(9) . 3_665 ?
Er1 O1 Er1 113.39(8) . 3_665 ?
C6 O1 Er1 122.76(18) . 3_665 ?
C6 O1 Er1 118.60(18) . . ?
C13 O2 Er1 126.07(19) . . ?
C12 O3 C14 117.1(3) . . ?
C16 O4 Er1 135.4(2) . . ?
C18 O5 Er1 135.7(2) . . ?
Er1 O6 H6A 122.3 . . ?
Er1 O6 H6B 122.7 . . ?
H6A O6 H6B 109.8 . . ?
C1 N1 Er1 124.4(2) . 3_665 ?
C1 N1 C5 117.8(3) . . ?
C5 N1 Er1 117.47(19) . 3_665 ?
C6 N2 N3 109.1(2) . . ?
N2 N3 Er1 119.35(18) . . ?
C7 N3 Er1 126.4(2) . . ?
C7 N3 N2 113.9(3) . . ?
N1 C1 H1 118.5 . . ?
N1 C1 C2 123.0(3) . . ?
C2 C1 H1 118.5 . . ?
C1 C2 H2 120.6 . . ?
C1 C2 C3 118.8(3) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.0(3) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.1(3) . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 122.3(3) . . ?
N1 C5 C6 114.5(3) . . ?
C4 C5 C6 123.1(3) . . ?
O1 C6 C5 116.5(3) . . ?
N2 C6 O1 125.7(3) . . ?
N2 C6 C5 117.8(3) . . ?
N3 C7 H7 118.1 . . ?
N3 C7 C8 123.9(3) . . ?
C8 C7 H7 118.1 . . ?
C9 C8 C7 117.6(3) . . ?
C9 C8 C13 120.8(3) . . ?
C13 C8 C7 121.2(3) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.8(3) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.7(3) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11 119.8 . . ?
O3 C12 C11 125.0(3) . . ?
O3 C12 C13 113.6(3) . . ?
C11 C12 C13 121.4(3) . . ?
O2 C13 C8 124.4(3) . . ?
O2 C13 C12 118.8(3) . . ?
C8 C13 C12 116.7(3) . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C16 C15 H15C 109.5 . . ?
O4 C16 C15 116.7(3) . . ?
O4 C16 C17 123.9(3) . . ?
C17 C16 C15 119.3(3) . . ?
C16 C17 H17 118.2 . . ?
C16 C17 C18 123.6(3) . . ?
C18 C17 H17 118.2 . . ?
O5 C18 C17 123.9(3) . . ?
O5 C18 C19 116.8(3) . . ?
C17 C18 C19 119.3(3) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 O7 H7A 95.8 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
C21 C20 H20C 109.5 . . ?
O7 C21 C20 111.3(3) . . ?
O7 C21 H21 108.5 . . ?
O7 C21 C22 106.5(3) . . ?
C20 C21 H21 108.5 . . ?
C20 C21 C22 113.3(4) . . ?
C22 C21 H21 108.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 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
Er1 O1 C6 N2 -12.1(4) . . . . ?
Er1 O1 C6 N2 -164.8(2) 3_665 . . . ?
Er1 O1 C6 C5 170.28(19) . . . . ?
Er1 O1 C6 C5 17.6(3) 3_665 . . . ?
Er1 O2 C13 C8 41.2(4) . . . . ?
Er1 O2 C13 C12 -142.1(2) . . . . ?
Er1 O4 C16 C15 -175.9(2) . . . . ?
Er1 O4 C16 C17 5.1(5) . . . . ?
Er1 O5 C18 C17 -24.7(5) . . . . ?
Er1 O5 C18 C19 156.1(2) . . . . ?
Er1 N1 C1 C2 -172.6(2) 3_665 . . . ?
Er1 N1 C5 C4 172.0(2) 3_665 . . . ?
Er1 N1 C5 C6 -10.3(3) 3_665 . . . ?
Er1 N3 C7 C8 -17.1(4) . . . . ?
O3 C12 C13 O2 -2.2(4) . . . . ?
O3 C12 C13 C8 174.7(3) . . . . ?
O4 C16 C17 C18 10.1(5) . . . . ?
N1 C1 C2 C3 0.3(5) . . . . ?
N1 C5 C6 O1 -3.7(4) . . . . ?
N1 C5 C6 N2 178.5(3) . . . . ?
N2 N3 C7 C8 170.1(3) . . . . ?
N3 N2 C6 O1 -1.0(4) . . . . ?
N3 N2 C6 C5 176.6(2) . . . . ?
N3 C7 C8 C9 168.2(3) . . . . ?
N3 C7 C8 C13 -18.8(5) . . . . ?
C1 N1 C5 C4 -1.6(5) . . . . ?
C1 N1 C5 C6 176.1(3) . . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C2 C3 C4 C5 -0.8(5) . . . . ?
C3 C4 C5 N1 1.7(5) . . . . ?
C3 C4 C5 C6 -175.8(3) . . . . ?
C4 C5 C6 O1 174.0(3) . . . . ?
C4 C5 C6 N2 -3.8(4) . . . . ?
C5 N1 C1 C2 0.6(5) . . . . ?
C6 N2 N3 Er1 13.3(3) . . . . ?
C6 N2 N3 C7 -173.3(3) . . . . ?
C7 C8 C9 C10 172.0(3) . . . . ?
C7 C8 C13 O2 8.3(4) . . . . ?
C7 C8 C13 C12 -168.5(3) . . . . ?
C8 C9 C10 C11 -2.7(5) . . . . ?
C9 C8 C13 O2 -178.9(3) . . . . ?
C9 C8 C13 C12 4.3(4) . . . . ?
C9 C10 C11 C12 3.0(5) . . . . ?
C10 C11 C12 O3 -178.1(3) . . . . ?
C10 C11 C12 C13 0.5(5) . . . . ?
C11 C12 C13 O2 179.0(3) . . . . ?
C11 C12 C13 C8 -4.1(4) . . . . ?
C13 C8 C9 C10 -1.0(5) . . . . ?
C14 O3 C12 C11 5.4(5) . . . . ?
C14 O3 C12 C13 -173.3(3) . . . . ?
C15 C16 C17 C18 -169.0(3) . . . . ?
C16 C17 C18 O5 -1.1(5) . . . . ?
C16 C17 C18 C19 178.1(3) . . . . ?

_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_shelxl_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 1945851'
loop_
_audit_author_name
_audit_author_address
'XueMei Zhang'
;Tianjin University
China
;
_audit_update_record             
;
2020-10-06 deposited with the CCDC.	2020-10-09 downloaded from the CCDC.
;
_audit_creation_date             2020-09-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H20 Eu N3 O6, C3 H8 O'
_chemical_formula_sum            'C22 H28 Eu N3 O7'
_chemical_formula_weight         598.43
_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      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                   11.320(2)
_cell_length_b                   14.828(3)
_cell_length_c                   15.511(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.46(3)
_cell_angle_gamma                90
_cell_volume                     2454.7(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7103
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.8984
_cell_measurement_theta_min      1.9081
_shelx_estimated_absorpt_T_max   0.746
_shelx_estimated_absorpt_T_min   0.624
_exptl_absorpt_coefficient_mu    2.600
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.8783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24272
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.878
_diffrn_reflns_theta_min         2.351
_diffrn_ambient_temperature      113.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4606
_reflns_number_total             5855
_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       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         1.177
_refine_diff_density_min         -1.513
_refine_diff_density_rms         0.160
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         5855
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0312
_refine_ls_restrained_S_all      1.019
_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)+(0.0378P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0709
_refine_ls_wR_factor_ref         0.0753
_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, All O(H) groups, All O(H,H) groups
2. Restrained distances
 O6-H6A = O6-H6B
 0.85 with sigma of 0.01
 H6A-H6B
 1.4 with sigma of 0.01
3.a Riding coordinates:
 O6(H6A,H6B), O7(H7A)
3.b Ternary CH refined with riding coordinates:
 C21(H21)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C9(H9), C10(H10), C11(H11), C17(H17)
3.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.65709(2) 0.43712(2) 0.07402(2) 0.01090(6) Uani 1 1 d . . . . .
O1 O 0.5685(2) 0.57137(13) -0.00657(15) 0.0125(5) Uani 1 1 d . . . . .
O2 O 0.8203(2) 0.45735(14) 0.20782(14) 0.0136(5) Uani 1 1 d . . . . .
O3 O 0.9630(2) 0.38291(17) 0.35898(16) 0.0244(6) Uani 1 1 d . . . . .
O4 O 0.6310(2) 0.39861(16) -0.08245(15) 0.0180(5) Uani 1 1 d . . . . .
O5 O 0.7990(2) 0.32227(15) 0.07296(15) 0.0175(5) Uani 1 1 d . . . . .
O6 O 0.5667(2) 0.50030(17) 0.18130(16) 0.0256(6) Uani 1 1 d D . . . .
H6A H 0.505509 0.537367 0.164908 0.038 Uiso 1 1 d DR U . . .
H6B H 0.609769 0.508587 0.237008 0.038 Uiso 1 1 d DR U . . .
N1 N 0.4471(3) 0.70121(17) -0.11819(17) 0.0150(6) Uani 1 1 d . . . . .
N2 N 0.7600(3) 0.62027(17) -0.01391(18) 0.0147(6) Uani 1 1 d . . . . .
N3 N 0.8056(3) 0.54846(17) 0.04882(18) 0.0143(6) Uani 1 1 d . . . . .
C1 C 0.3823(3) 0.7694(2) -0.1699(2) 0.0177(7) Uani 1 1 d . . . . .
H1 H 0.293945 0.770949 -0.184273 0.021 Uiso 1 1 calc R U . . .
C2 C 0.4392(3) 0.8374(2) -0.2029(2) 0.0214(8) Uani 1 1 d . . . . .
H2 H 0.390906 0.884713 -0.239102 0.026 Uiso 1 1 calc R U . . .
C3 C 0.5676(3) 0.8350(2) -0.1822(3) 0.0258(8) Uani 1 1 d . . . . .
H3 H 0.608737 0.881065 -0.203982 0.031 Uiso 1 1 calc R U . . .
C4 C 0.6361(3) 0.7654(2) -0.1295(2) 0.0220(8) Uani 1 1 d . . . . .
H4 H 0.724381 0.762502 -0.115254 0.026 Uiso 1 1 calc R U . . .
C5 C 0.5727(3) 0.6996(2) -0.0977(2) 0.0134(6) Uani 1 1 d . . . . .
C6 C 0.6380(3) 0.6249(2) -0.0363(2) 0.0130(6) Uani 1 1 d . . . . .
C7 C 0.9265(3) 0.5438(2) 0.0802(2) 0.0146(7) Uani 1 1 d . . . . .
H7 H 0.972783 0.580411 0.052554 0.018 Uiso 1 1 calc R U . . .
C8 C 0.9955(3) 0.4853(2) 0.1555(2) 0.0134(6) Uani 1 1 d . . . . .
C9 C 1.1245(3) 0.4723(2) 0.1710(2) 0.0179(7) Uani 1 1 d . . . . .
H9 H 1.160461 0.494998 0.128031 0.021 Uiso 1 1 calc R U . . .
C10 C 1.1984(3) 0.4276(2) 0.2469(2) 0.0211(7) Uani 1 1 d . . . . .
H10 H 1.284287 0.417111 0.255119 0.025 Uiso 1 1 calc R U . . .
C11 C 1.1476(3) 0.3971(2) 0.3125(2) 0.0209(7) Uani 1 1 d . . . . .
H11 H 1.200032 0.368689 0.366648 0.025 Uiso 1 1 calc R U . . .
C12 C 1.0224(3) 0.4082(2) 0.2989(2) 0.0175(7) Uani 1 1 d . . . . .
C13 C 0.9400(3) 0.4500(2) 0.2182(2) 0.0127(6) Uani 1 1 d . . . . .
C14 C 1.0397(4) 0.3487(3) 0.4458(2) 0.0319(9) Uani 1 1 d . . . . .
H14A H 1.081915 0.293588 0.436714 0.048 Uiso 1 1 calc R U . . .
H14B H 0.987296 0.335077 0.483230 0.048 Uiso 1 1 calc R U . . .
H14C H 1.102529 0.393993 0.476811 0.048 Uiso 1 1 calc R U . . .
C15 C 0.6406(3) 0.3495(3) -0.2252(2) 0.0249(8) Uani 1 1 d . . . . .
H15A H 0.558000 0.320618 -0.243843 0.037 Uiso 1 1 calc R U . . .
H15B H 0.696811 0.314528 -0.248667 0.037 Uiso 1 1 calc R U . . .
H15C H 0.632390 0.410828 -0.250008 0.037 Uiso 1 1 calc R U . . .
C16 C 0.6938(3) 0.3533(2) -0.1221(2) 0.0168(7) Uani 1 1 d . . . . .
C17 C 0.8043(3) 0.3079(2) -0.0773(2) 0.0167(7) Uani 1 1 d . . . . .
H17 H 0.850477 0.284073 -0.113199 0.020 Uiso 1 1 calc R U . . .
C18 C 0.8524(3) 0.2947(2) 0.0177(2) 0.0163(7) Uani 1 1 d . . . . .
C19 C 0.9727(3) 0.2436(3) 0.0585(3) 0.0271(8) Uani 1 1 d . . . . .
H19A H 1.035481 0.283019 0.100331 0.041 Uiso 1 1 calc R U . . .
H19B H 1.003104 0.223112 0.009580 0.041 Uiso 1 1 calc R U . . .
H19C H 0.958042 0.191280 0.092207 0.041 Uiso 1 1 calc R U . . .
O7 O 0.7674(2) 0.99988(17) 0.14672(16) 0.0251(6) Uani 1 1 d . . . . .
H7A H 0.708892 0.970309 0.156634 0.038 Uiso 1 1 d R U . . .
C20 C 0.8202(4) 0.8461(3) 0.1209(3) 0.0351(10) Uani 1 1 d . . . . .
H20A H 0.904552 0.850607 0.166076 0.053 Uiso 1 1 calc R U . . .
H20B H 0.821010 0.803333 0.072976 0.053 Uiso 1 1 calc R U . . .
H20C H 0.761739 0.824983 0.151051 0.053 Uiso 1 1 calc R U . . .
C21 C 0.7793(4) 0.9375(2) 0.0790(2) 0.0256(8) Uani 1 1 d . . . . .
H21 H 0.696219 0.931388 0.029561 0.031 Uiso 1 1 calc R U . . .
C22 C 0.8716(4) 0.9792(3) 0.0393(3) 0.0409(11) Uani 1 1 d . . . . .
H22A H 0.843989 1.040236 0.017591 0.061 Uiso 1 1 calc R U . . .
H22B H 0.876195 0.942346 -0.011953 0.061 Uiso 1 1 calc R U . . .
H22C H 0.954503 0.982024 0.086475 0.061 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 Eu1 3.9946(12) 3_665 ?
Eu1 O1 2.387(2) . ?
Eu1 O1 2.419(2) 3_665 ?
Eu1 O2 2.292(2) . ?
Eu1 O4 2.414(2) . ?
Eu1 O5 2.345(2) . ?
Eu1 O6 2.414(2) . ?
Eu1 N1 2.570(3) 3_665 ?
Eu1 N3 2.479(3) . ?
Eu1 C6 3.237(3) . ?
Eu1 C13 3.244(3) . ?
O1 C6 1.306(4) . ?
O2 C13 1.315(4) . ?
O3 C12 1.371(4) . ?
O3 C14 1.430(4) . ?
O4 C16 1.276(4) . ?
O5 C18 1.269(4) . ?
O6 H6A 0.8539 . ?
O6 H6B 0.8478 . ?
N1 C1 1.346(4) . ?
N1 C5 1.351(4) . ?
N2 N3 1.419(3) . ?
N2 C6 1.309(4) . ?
N3 C7 1.292(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.382(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.380(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.395(5) . ?
C5 C6 1.487(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.456(4) . ?
C8 C9 1.412(4) . ?
C8 C13 1.422(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.368(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.400(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.372(5) . ?
C12 C13 1.429(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C15 C16 1.510(4) . ?
C16 C17 1.386(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.404(4) . ?
C18 C19 1.502(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O7 H7A 0.8499 . ?
O7 C21 1.439(4) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C20 C21 1.507(5) . ?
C21 H21 1.0000 . ?
C21 C22 1.511(5) . ?
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 Eu1 Eu1 33.51(5) 3_665 3_665 ?
O1 Eu1 Eu1 34.03(5) . 3_665 ?
O1 Eu1 O1 67.54(8) . 3_665 ?
O1 Eu1 O4 77.36(8) . . ?
O1 Eu1 O6 80.60(8) . . ?
O1 Eu1 N1 64.01(8) 3_665 3_665 ?
O1 Eu1 N1 130.94(8) . 3_665 ?
O1 Eu1 N3 129.82(8) 3_665 . ?
O1 Eu1 N3 63.30(8) . . ?
O1 Eu1 C6 20.52(8) . . ?
O1 Eu1 C6 86.64(8) 3_665 . ?
O1 Eu1 C13 163.50(8) 3_665 . ?
O1 Eu1 C13 117.27(7) . . ?
O2 Eu1 Eu1 138.94(6) . 3_665 ?
O2 Eu1 O1 115.87(7) . . ?
O2 Eu1 O1 144.55(8) . 3_665 ?
O2 Eu1 O4 137.14(8) . . ?
O2 Eu1 O5 75.76(8) . . ?
O2 Eu1 O6 73.98(8) . . ?
O2 Eu1 N1 99.55(8) . 3_665 ?
O2 Eu1 N3 70.80(8) . . ?
O2 Eu1 C6 104.93(8) . . ?
O2 Eu1 C13 19.16(8) . . ?
O4 Eu1 Eu1 75.23(6) . 3_665 ?
O4 Eu1 O1 78.15(8) . 3_665 ?
O4 Eu1 O6 147.87(8) . . ?
O4 Eu1 N1 99.54(8) . 3_665 ?
O4 Eu1 N3 82.03(9) . . ?
O4 Eu1 C6 73.00(8) . . ?
O4 Eu1 C13 117.98(8) . . ?
O5 Eu1 Eu1 144.66(5) . 3_665 ?
O5 Eu1 O1 125.88(7) . 3_665 ?
O5 Eu1 O1 140.48(8) . . ?
O5 Eu1 O4 71.09(8) . . ?
O5 Eu1 O6 137.34(8) . . ?
O5 Eu1 N1 78.37(9) . 3_665 ?
O5 Eu1 N3 88.87(9) . . ?
O5 Eu1 C6 123.09(8) . . ?
O5 Eu1 C13 61.72(8) . . ?
O6 Eu1 Eu1 73.41(6) . 3_665 ?
O6 Eu1 O1 71.92(8) . 3_665 ?
O6 Eu1 N1 77.79(9) . 3_665 ?
O6 Eu1 N3 108.41(9) . . ?
O6 Eu1 C6 93.54(8) . . ?
O6 Eu1 C13 92.86(8) . . ?
N1 Eu1 Eu1 97.25(6) 3_665 3_665 ?
N1 Eu1 C6 150.65(8) 3_665 . ?
N1 Eu1 C13 107.36(8) 3_665 . ?
N3 Eu1 Eu1 96.85(6) . 3_665 ?
N3 Eu1 N1 165.74(9) . 3_665 ?
N3 Eu1 C6 43.37(8) . . ?
N3 Eu1 C13 60.25(8) . . ?
C6 Eu1 Eu1 53.48(6) . 3_665 ?
C6 Eu1 C13 100.98(8) . . ?
C13 Eu1 Eu1 148.69(5) . 3_665 ?
Eu1 O1 Eu1 112.46(8) . 3_665 ?
C6 O1 Eu1 119.63(19) . . ?
C6 O1 Eu1 123.57(19) . 3_665 ?
C13 O2 Eu1 125.93(19) . . ?
C12 O3 C14 117.1(3) . . ?
C16 O4 Eu1 135.1(2) . . ?
C18 O5 Eu1 136.0(2) . . ?
Eu1 O6 H6A 122.2 . . ?
Eu1 O6 H6B 121.8 . . ?
H6A O6 H6B 110.1 . . ?
C1 N1 Eu1 123.5(2) . 3_665 ?
C1 N1 C5 118.4(3) . . ?
C5 N1 Eu1 117.6(2) . 3_665 ?
C6 N2 N3 109.4(3) . . ?
N2 N3 Eu1 119.81(19) . . ?
C7 N3 Eu1 126.4(2) . . ?
C7 N3 N2 113.3(3) . . ?
N1 C1 H1 118.7 . . ?
N1 C1 C2 122.7(3) . . ?
C2 C1 H1 118.7 . . ?
C1 C2 H2 120.7 . . ?
C3 C2 C1 118.6(3) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.7(3) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.7 . . ?
C3 C4 C5 118.6(3) . . ?
C5 C4 H4 120.7 . . ?
N1 C5 C4 122.0(3) . . ?
N1 C5 C6 115.1(3) . . ?
C4 C5 C6 122.9(3) . . ?
O1 C6 Eu1 39.85(14) . . ?
O1 C6 N2 125.6(3) . . ?
O1 C6 C5 116.7(3) . . ?
N2 C6 Eu1 86.34(19) . . ?
N2 C6 C5 117.7(3) . . ?
C5 C6 Eu1 155.6(2) . . ?
N3 C7 H7 118.3 . . ?
N3 C7 C8 123.5(3) . . ?
C8 C7 H7 118.3 . . ?
C9 C8 C7 117.7(3) . . ?
C9 C8 C13 120.1(3) . . ?
C13 C8 C7 121.8(3) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.9(3) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.1(3) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.2(3) . . ?
C12 C11 H11 119.9 . . ?
O3 C12 C11 125.3(3) . . ?
O3 C12 C13 112.9(3) . . ?
C11 C12 C13 121.8(3) . . ?
O2 C13 Eu1 34.91(13) . . ?
O2 C13 C8 123.9(3) . . ?
O2 C13 C12 119.2(3) . . ?
C8 C13 Eu1 96.31(19) . . ?
C8 C13 C12 116.8(3) . . ?
C12 C13 Eu1 141.7(2) . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C16 C15 H15C 109.5 . . ?
O4 C16 C15 116.1(3) . . ?
O4 C16 C17 124.6(3) . . ?
C17 C16 C15 119.2(3) . . ?
C16 C17 H17 117.8 . . ?
C16 C17 C18 124.3(3) . . ?
C18 C17 H17 117.8 . . ?
O5 C18 C17 123.9(3) . . ?
O5 C18 C19 116.6(3) . . ?
C17 C18 C19 119.5(3) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 O7 H7A 93.9 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
C21 C20 H20C 109.5 . . ?
O7 C21 C20 110.7(3) . . ?
O7 C21 H21 109.0 . . ?
O7 C21 C22 106.2(3) . . ?
C20 C21 H21 109.0 . . ?
C20 C21 C22 112.9(4) . . ?
C22 C21 H21 109.0 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 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
Eu1 O1 C6 Eu1 -154.8(3) 3_665 . . . ?
Eu1 O1 C6 N2 -166.5(2) 3_665 . . . ?
Eu1 O1 C6 N2 -11.7(4) . . . . ?
Eu1 O1 C6 C5 171.05(19) . . . . ?
Eu1 O1 C6 C5 16.2(4) 3_665 . . . ?
Eu1 O2 C13 C8 43.0(4) . . . . ?
Eu1 O2 C13 C12 -140.3(2) . . . . ?
Eu1 O4 C16 C15 -178.4(2) . . . . ?
Eu1 O4 C16 C17 2.2(5) . . . . ?
Eu1 O5 C18 C17 -24.9(5) . . . . ?
Eu1 O5 C18 C19 156.4(2) . . . . ?
Eu1 N1 C1 C2 -171.4(2) 3_665 . . . ?
Eu1 N1 C5 C4 171.2(2) 3_665 . . . ?
Eu1 N1 C5 C6 -11.1(3) 3_665 . . . ?
Eu1 N3 C7 C8 -17.5(5) . . . . ?
O3 C12 C13 Eu1 -38.3(5) . . . . ?
O3 C12 C13 O2 -2.2(4) . . . . ?
O3 C12 C13 C8 174.8(3) . . . . ?
O4 C16 C17 C18 9.6(5) . . . . ?
N1 C1 C2 C3 0.2(5) . . . . ?
N1 C5 C6 Eu1 11.7(7) . . . . ?
N1 C5 C6 O1 -2.2(4) . . . . ?
N1 C5 C6 N2 -179.7(3) . . . . ?
N2 N3 C7 C8 170.1(3) . . . . ?
N3 N2 C6 Eu1 -8.2(2) . . . . ?
N3 N2 C6 O1 -0.7(4) . . . . ?
N3 N2 C6 C5 176.6(3) . . . . ?
N3 C7 C8 C9 167.2(3) . . . . ?
N3 C7 C8 C13 -19.6(5) . . . . ?
C1 N1 C5 C4 -0.9(5) . . . . ?
C1 N1 C5 C6 176.9(3) . . . . ?
C1 C2 C3 C4 0.1(6) . . . . ?
C2 C3 C4 C5 -0.7(6) . . . . ?
C3 C4 C5 N1 1.1(5) . . . . ?
C3 C4 C5 C6 -176.4(3) . . . . ?
C4 C5 C6 Eu1 -170.6(4) . . . . ?
C4 C5 C6 O1 175.5(3) . . . . ?
C4 C5 C6 N2 -2.0(5) . . . . ?
C5 N1 C1 C2 0.2(5) . . . . ?
C6 N2 N3 Eu1 12.3(3) . . . . ?
C6 N2 N3 C7 -174.7(3) . . . . ?
C7 C8 C9 C10 171.9(3) . . . . ?
C7 C8 C13 Eu1 31.6(3) . . . . ?
C7 C8 C13 O2 8.5(5) . . . . ?
C7 C8 C13 C12 -168.3(3) . . . . ?
C8 C9 C10 C11 -2.6(5) . . . . ?
C9 C8 C13 Eu1 -155.3(3) . . . . ?
C9 C8 C13 O2 -178.4(3) . . . . ?
C9 C8 C13 C12 4.7(4) . . . . ?
C9 C10 C11 C12 3.1(5) . . . . ?
C10 C11 C12 O3 -178.5(3) . . . . ?
C10 C11 C12 C13 0.5(5) . . . . ?
C11 C12 C13 Eu1 142.6(3) . . . . ?
C11 C12 C13 O2 178.7(3) . . . . ?
C11 C12 C13 C8 -4.3(5) . . . . ?
C13 C8 C9 C10 -1.4(5) . . . . ?
C14 O3 C12 C11 5.1(5) . . . . ?
C14 O3 C12 C13 -173.9(3) . . . . ?
C15 C16 C17 C18 -169.7(3) . . . . ?
C16 C17 C18 O5 0.8(5) . . . . ?
C16 C17 C18 C19 179.4(3) . . . . ?

_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_shelxl_CCDC6
_database_code_depnum_ccdc_archive 'CCDC 1947943'
loop_
_audit_author_name
_audit_author_address
'XueMei Zhang'
;Tianjin University
China
;
_audit_update_record             
;
2020-10-06 deposited with the CCDC.	2020-10-09 downloaded from the CCDC.
;
_audit_creation_date             2020-09-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H20 N3 O6 Y, C3 H8 O'
_chemical_formula_sum            'C22 H28 N3 O7 Y'
_chemical_formula_weight         535.38
_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'
Y Y -2.7962 3.5667 '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                   11.327(2)
_cell_length_b                   14.721(3)
_cell_length_c                   15.534(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.86(3)
_cell_angle_gamma                90
_cell_volume                     2436.3(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5743
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.8704
_cell_measurement_theta_min      1.3937
_shelx_estimated_absorpt_T_max   0.758
_shelx_estimated_absorpt_T_min   0.641
_exptl_absorpt_coefficient_mu    2.439
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.7828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0764
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            28884
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.885
_diffrn_reflns_theta_min         2.360
_diffrn_ambient_temperature      113.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4604
_reflns_number_total             5788
_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       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         1.092
_refine_diff_density_min         -0.819
_refine_diff_density_rms         0.105
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         5788
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0489
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0547P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1062
_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, All O(H) groups, All O(H,H) groups
2.a Riding coordinates:
 O6(H6A,H6B), O7(H7A)
2.b Ternary CH refined with riding coordinates:
 C21(H21)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C9(H9), C10(H10), C11(H11), C17(H17)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
Y1 Y 0.65573(2) 0.43782(2) 0.07306(2) 0.01461(9) Uani 1 1 d . . . . .
O1 O 0.56588(17) 0.57022(11) -0.00614(12) 0.0160(4) Uani 1 1 d . . . . .
O2 O 0.81688(17) 0.45519(12) 0.20607(12) 0.0178(4) Uani 1 1 d . . . . .
O3 O 0.95919(19) 0.38032(14) 0.35887(13) 0.0284(5) Uani 1 1 d . . . . .
O4 O 0.62861(18) 0.40043(13) -0.08048(13) 0.0214(4) Uani 1 1 d . . . . .
O5 O 0.79516(18) 0.32356(12) 0.07340(13) 0.0203(4) Uani 1 1 d . . . . .
O6 O 0.57169(19) 0.50133(14) 0.17771(13) 0.0278(5) Uani 1 1 d . . . . .
H6A H 0.510503 0.538415 0.161306 0.042 Uiso 1 1 d R U . . .
H6B H 0.614763 0.509625 0.233406 0.042 Uiso 1 1 d R U . . .
N1 N 0.4420(2) 0.69888(14) -0.11983(15) 0.0173(5) Uani 1 1 d . . . . .
N2 N 0.7566(2) 0.61800(15) -0.01604(15) 0.0183(5) Uani 1 1 d . . . . .
N3 N 0.8024(2) 0.54617(14) 0.04741(15) 0.0171(5) Uani 1 1 d . . . . .
C1 C 0.3763(3) 0.76769(18) -0.17169(19) 0.0216(6) Uani 1 1 d . . . . .
H1 H 0.287844 0.769066 -0.186193 0.026 Uiso 1 1 calc R U . . .
C2 C 0.4330(3) 0.83639(19) -0.2046(2) 0.0248(7) Uani 1 1 d . . . . .
H2 H 0.384315 0.884335 -0.240355 0.030 Uiso 1 1 calc R U . . .
C3 C 0.5612(3) 0.8340(2) -0.1846(2) 0.0290(7) Uani 1 1 d . . . . .
H3 H 0.601734 0.880104 -0.207127 0.035 Uiso 1 1 calc R U . . .
C4 C 0.6308(3) 0.76410(19) -0.1314(2) 0.0239(7) Uani 1 1 d . . . . .
H4 H 0.719252 0.761308 -0.116886 0.029 Uiso 1 1 calc R U . . .
C5 C 0.5677(3) 0.69826(17) -0.09995(18) 0.0168(6) Uani 1 1 d . . . . .
C6 C 0.6354(3) 0.62300(17) -0.03708(18) 0.0161(6) Uani 1 1 d . . . . .
C7 C 0.9235(3) 0.54089(18) 0.07936(19) 0.0183(6) Uani 1 1 d . . . . .
H7 H 0.969816 0.577078 0.051434 0.022 Uiso 1 1 calc R U . . .
C8 C 0.9931(3) 0.48279(18) 0.15560(18) 0.0177(6) Uani 1 1 d . . . . .
C9 C 1.1223(3) 0.46992(18) 0.1726(2) 0.0211(6) Uani 1 1 d . . . . .
H9 H 1.158519 0.493044 0.130134 0.025 Uiso 1 1 calc R U . . .
C10 C 1.1969(3) 0.42505(19) 0.2485(2) 0.0252(7) Uani 1 1 d . . . . .
H10 H 1.283010 0.414724 0.257342 0.030 Uiso 1 1 calc R U . . .
C11 C 1.1450(3) 0.3943(2) 0.3136(2) 0.0242(7) Uani 1 1 d . . . . .
H11 H 1.197055 0.365284 0.367784 0.029 Uiso 1 1 calc R U . . .
C12 C 1.0187(3) 0.40603(19) 0.29915(19) 0.0209(6) Uani 1 1 d . . . . .
C13 C 0.9363(3) 0.44730(17) 0.21725(18) 0.0159(6) Uani 1 1 d . . . . .
C14 C 1.0359(3) 0.3471(2) 0.4460(2) 0.0375(8) Uani 1 1 d . . . . .
H14A H 1.076564 0.290492 0.438103 0.056 Uiso 1 1 calc R U . . .
H14B H 0.983688 0.335505 0.483918 0.056 Uiso 1 1 calc R U . . .
H14C H 1.100046 0.392354 0.476099 0.056 Uiso 1 1 calc R U . . .
C15 C 0.6395(3) 0.3545(2) -0.22360(19) 0.0302(7) Uani 1 1 d . . . . .
H15A H 0.557884 0.323776 -0.243029 0.045 Uiso 1 1 calc R U . . .
H15B H 0.697027 0.321441 -0.247315 0.045 Uiso 1 1 calc R U . . .
H15C H 0.628908 0.416707 -0.247451 0.045 Uiso 1 1 calc R U . . .
C16 C 0.6927(3) 0.35686(18) -0.12065(19) 0.0196(6) Uani 1 1 d . . . . .
C17 C 0.8039(3) 0.31146(18) -0.07518(19) 0.0216(6) Uani 1 1 d . . . . .
H17 H 0.851716 0.289153 -0.110407 0.026 Uiso 1 1 calc R U . . .
C18 C 0.8497(3) 0.29656(18) 0.0194(2) 0.0192(6) Uani 1 1 d . . . . .
C19 C 0.9700(3) 0.2444(2) 0.0612(2) 0.0319(8) Uani 1 1 d . . . . .
H19A H 1.031906 0.283070 0.105398 0.048 Uiso 1 1 calc R U . . .
H19B H 1.002531 0.225798 0.012908 0.048 Uiso 1 1 calc R U . . .
H19C H 0.953877 0.190416 0.092374 0.048 Uiso 1 1 calc R U . . .
O7 O 0.7681(2) 0.99850(14) 0.14702(14) 0.0301(5) Uani 1 1 d . . . . .
H7A H 0.709555 0.968930 0.156933 0.045 Uiso 1 1 d R U . . .
C20 C 0.8240(4) 0.8443(2) 0.1192(3) 0.0432(9) Uani 1 1 d . . . . .
H20A H 0.906718 0.849500 0.166857 0.065 Uiso 1 1 calc R U . . .
H20B H 0.829402 0.803304 0.070994 0.065 Uiso 1 1 calc R U . . .
H20C H 0.763681 0.820068 0.145980 0.065 Uiso 1 1 calc R U . . .
C21 C 0.7812(3) 0.9369(2) 0.0788(2) 0.0286(7) Uani 1 1 d . . . . .
H21 H 0.697976 0.930490 0.029091 0.034 Uiso 1 1 calc R U . . .
C22 C 0.8724(4) 0.9806(3) 0.0395(3) 0.0457(10) Uani 1 1 d . . . . .
H22A H 0.840128 1.040042 0.013770 0.069 Uiso 1 1 calc R U . . .
H22B H 0.882305 0.941715 -0.008856 0.069 Uiso 1 1 calc R U . . .
H22C H 0.953926 0.988284 0.087958 0.069 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
Y1 Y1 3.9383(12) 3_665 ?
Y1 O1 2.3447(17) . ?
Y1 O1 2.371(2) 3_665 ?
Y1 O2 2.259(2) . ?
Y1 O4 2.364(2) . ?
Y1 O5 2.3061(19) . ?
Y1 O6 2.340(2) . ?
Y1 N1 2.520(2) 3_665 ?
Y1 N3 2.432(2) . ?
O1 C6 1.308(3) . ?
O2 C13 1.309(3) . ?
O3 C12 1.372(3) . ?
O3 C14 1.424(3) . ?
O4 C16 1.279(3) . ?
O5 C18 1.263(3) . ?
O6 H6A 0.8505 . ?
O6 H6B 0.8455 . ?
N1 C1 1.350(3) . ?
N1 C5 1.350(3) . ?
N2 N3 1.418(3) . ?
N2 C6 1.301(3) . ?
N3 C7 1.292(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.385(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.379(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(4) . ?
C5 C6 1.504(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.457(4) . ?
C8 C9 1.409(4) . ?
C8 C13 1.423(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.366(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.405(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.381(4) . ?
C12 C13 1.433(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C15 C16 1.506(4) . ?
C16 C17 1.388(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.399(4) . ?
C18 C19 1.505(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O7 H7A 0.8496 . ?
O7 C21 1.440(4) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C20 C21 1.509(4) . ?
C21 H21 1.0000 . ?
C21 C22 1.511(4) . ?
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 Y1 Y1 33.59(4) . 3_665 ?
O1 Y1 Y1 33.16(4) 3_665 3_665 ?
O1 Y1 O1 66.75(7) . 3_665 ?
O1 Y1 O4 77.27(7) . . ?
O1 Y1 N1 131.31(7) . 3_665 ?
O1 Y1 N1 65.36(7) 3_665 3_665 ?
O1 Y1 N3 129.90(7) 3_665 . ?
O1 Y1 N3 64.39(7) . . ?
O2 Y1 Y1 139.62(5) . 3_665 ?
O2 Y1 O1 144.36(7) . 3_665 ?
O2 Y1 O1 117.24(6) . . ?
O2 Y1 O4 137.46(7) . . ?
O2 Y1 O5 74.96(7) . . ?
O2 Y1 O6 73.28(7) . . ?
O2 Y1 N1 97.14(7) . 3_665 ?
O2 Y1 N3 71.99(7) . . ?
O4 Y1 Y1 75.10(5) . 3_665 ?
O4 Y1 O1 77.92(7) . 3_665 ?
O4 Y1 N1 100.70(7) . 3_665 ?
O4 Y1 N3 81.33(7) . . ?
O5 Y1 Y1 145.00(5) . 3_665 ?
O5 Y1 O1 125.93(6) . 3_665 ?
O5 Y1 O1 141.48(7) . . ?
O5 Y1 O4 71.74(7) . . ?
O5 Y1 O6 136.87(7) . . ?
O5 Y1 N1 77.55(7) . 3_665 ?
O5 Y1 N3 88.47(7) . . ?
O6 Y1 Y1 73.65(5) . 3_665 ?
O6 Y1 O1 72.81(7) . 3_665 ?
O6 Y1 O1 79.97(7) . . ?
O6 Y1 O4 148.21(7) . . ?
O6 Y1 N1 78.26(7) . 3_665 ?
O6 Y1 N3 108.28(8) . . ?
N1 Y1 Y1 98.17(5) 3_665 3_665 ?
N3 Y1 Y1 97.41(5) . 3_665 ?
N3 Y1 N1 164.29(7) . 3_665 ?
Y1 O1 Y1 113.25(7) . 3_665 ?
C6 O1 Y1 118.58(16) . . ?
C6 O1 Y1 123.24(16) . 3_665 ?
C13 O2 Y1 126.07(17) . . ?
C12 O3 C14 117.2(2) . . ?
C16 O4 Y1 135.10(18) . . ?
C18 O5 Y1 135.82(17) . . ?
Y1 O6 H6A 122.1 . . ?
Y1 O6 H6B 122.6 . . ?
H6A O6 H6B 110.0 . . ?
C1 N1 Y1 124.37(19) . 3_665 ?
C1 N1 C5 117.8(2) . . ?
C5 N1 Y1 117.45(16) . 3_665 ?
C6 N2 N3 108.8(2) . . ?
N2 N3 Y1 119.60(16) . . ?
C7 N3 Y1 126.33(18) . . ?
C7 N3 N2 113.7(2) . . ?
N1 C1 H1 118.7 . . ?
N1 C1 C2 122.5(3) . . ?
C2 C1 H1 118.7 . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.9(3) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.7(3) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.9 . . ?
C3 C4 C5 118.1(3) . . ?
C5 C4 H4 120.9 . . ?
N1 C5 C4 123.0(2) . . ?
N1 C5 C6 114.8(2) . . ?
C4 C5 C6 122.2(3) . . ?
O1 C6 C5 116.0(2) . . ?
N2 C6 O1 126.1(2) . . ?
N2 C6 C5 117.8(2) . . ?
N3 C7 H7 118.0 . . ?
N3 C7 C8 124.0(3) . . ?
C8 C7 H7 118.0 . . ?
C9 C8 C7 118.2(3) . . ?
C9 C8 C13 120.2(2) . . ?
C13 C8 C7 121.3(3) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 C8 121.7(3) . . ?
C10 C9 H9 119.2 . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.3(3) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 H11 119.8 . . ?
O3 C12 C11 125.1(3) . . ?
O3 C12 C13 113.3(2) . . ?
C11 C12 C13 121.6(3) . . ?
O2 C13 C8 124.2(2) . . ?
O2 C13 C12 119.2(3) . . ?
C8 C13 C12 116.5(2) . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C16 C15 H15C 109.5 . . ?
O4 C16 C15 116.2(3) . . ?
O4 C16 C17 124.1(3) . . ?
C17 C16 C15 119.7(3) . . ?
C16 C17 H17 118.0 . . ?
C16 C17 C18 124.0(3) . . ?
C18 C17 H17 118.0 . . ?
O5 C18 C17 123.9(3) . . ?
O5 C18 C19 116.7(3) . . ?
C17 C18 C19 119.4(3) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 O7 H7A 95.3 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
C21 C20 H20C 109.5 . . ?
O7 C21 C20 111.2(3) . . ?
O7 C21 H21 108.8 . . ?
O7 C21 C22 106.6(3) . . ?
C20 C21 H21 108.8 . . ?
C20 C21 C22 112.6(3) . . ?
C22 C21 H21 108.8 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 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
Y1 O1 C6 N2 -12.0(3) . . . . ?
Y1 O1 C6 N2 -165.4(2) 3_665 . . . ?
Y1 O1 C6 C5 17.0(3) 3_665 . . . ?
Y1 O1 C6 C5 170.46(16) . . . . ?
Y1 O2 C13 C8 42.3(3) . . . . ?
Y1 O2 C13 C12 -142.2(2) . . . . ?
Y1 O4 C16 C15 -176.79(18) . . . . ?
Y1 O4 C16 C17 4.7(4) . . . . ?
Y1 O5 C18 C17 -24.7(4) . . . . ?
Y1 O5 C18 C19 156.2(2) . . . . ?
Y1 N1 C1 C2 -172.5(2) 3_665 . . . ?
Y1 N1 C5 C4 172.2(2) 3_665 . . . ?
Y1 N1 C5 C6 -10.7(3) 3_665 . . . ?
Y1 N3 C7 C8 -17.4(4) . . . . ?
O3 C12 C13 O2 -1.1(4) . . . . ?
O3 C12 C13 C8 174.8(2) . . . . ?
O4 C16 C17 C18 9.7(5) . . . . ?
N1 C1 C2 C3 0.8(4) . . . . ?
N1 C5 C6 O1 -3.0(3) . . . . ?
N1 C5 C6 N2 179.3(2) . . . . ?
N2 N3 C7 C8 169.8(2) . . . . ?
N3 N2 C6 O1 -0.8(4) . . . . ?
N3 N2 C6 C5 176.7(2) . . . . ?
N3 C7 C8 C9 168.1(3) . . . . ?
N3 C7 C8 C13 -18.3(4) . . . . ?
C1 N1 C5 C4 -0.9(4) . . . . ?
C1 N1 C5 C6 176.3(2) . . . . ?
C1 C2 C3 C4 -0.8(5) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
C3 C4 C5 N1 0.9(4) . . . . ?
C3 C4 C5 C6 -176.1(3) . . . . ?
C4 C5 C6 O1 174.2(2) . . . . ?
C4 C5 C6 N2 -3.5(4) . . . . ?
C5 N1 C1 C2 0.1(4) . . . . ?
C6 N2 N3 Y1 12.8(3) . . . . ?
C6 N2 N3 C7 -173.9(2) . . . . ?
C7 C8 C9 C10 172.5(3) . . . . ?
C7 C8 C13 O2 7.4(4) . . . . ?
C7 C8 C13 C12 -168.3(2) . . . . ?
C8 C9 C10 C11 -2.8(4) . . . . ?
C9 C8 C13 O2 -179.1(2) . . . . ?
C9 C8 C13 C12 5.2(4) . . . . ?
C9 C10 C11 C12 2.6(5) . . . . ?
C10 C11 C12 O3 -178.6(3) . . . . ?
C10 C11 C12 C13 1.7(4) . . . . ?
C11 C12 C13 O2 178.6(3) . . . . ?
C11 C12 C13 C8 -5.5(4) . . . . ?
C13 C8 C9 C10 -1.2(4) . . . . ?
C14 O3 C12 C11 6.4(4) . . . . ?
C14 O3 C12 C13 -173.8(2) . . . . ?
C15 C16 C17 C18 -168.7(3) . . . . ?
C16 C17 C18 O5 -0.6(5) . . . . ?
C16 C17 C18 C19 178.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
