# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 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. 
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data_10671
_database_code_depnum_ccdc_archive 'CCDC 1817846'
loop_
_audit_author_name
_audit_author_address
Lirongyang
;Henan University
China
;
_audit_update_record             
;
2020-08-14 deposited with the CCDC.	2020-08-19 downloaded from the CCDC.
;
_audit_creation_date             2020-08-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H10 O11 Pr, C9 H8 N2'
_chemical_formula_sum            'C25 H18 N2 O11 Pr'
_chemical_formula_weight         663.32
_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'
Pr Pr -0.2180 2.8214 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.097(5)
_cell_length_b                   8.503(3)
_cell_length_c                   19.088(6)
_cell_angle_alpha                90
_cell_angle_beta                 114.725(4)
_cell_angle_gamma                90
_cell_volume                     2373.2(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9897
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.61
_cell_measurement_theta_min      2.67
_shelx_estimated_absorpt_T_max   0.866
_shelx_estimated_absorpt_T_min   0.515
_exptl_absorpt_coefficient_mu    2.123
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1174 before and 0.0567 after correction. The Ratio of minimum to maximum transmission is 0.6300. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.857
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1316
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14902
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.614
_diffrn_reflns_theta_min         2.173
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker Smart APEX II CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5426
_reflns_number_total             5894
_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       'APEX 2'
_computing_data_collection       'APEX 2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.775
_refine_diff_density_min         -0.723
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         5894
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0254
_refine_ls_restrained_S_all      1.043
_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)+(0.0223P)²+1.3097P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0657
_refine_ls_wR_factor_ref         0.0673
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All O(H,H) groups
2.a Riding coordinates:
 O1W(H1WA,H1WB), O2W(H2WA,H2WB)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C17(H17),
 C18(H18), C20(H20), C21(H21), C23(H23), C24(H24), C25(H25)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pr1 Pr 0.86592(2) 0.08878(2) 0.96316(2) 0.01377(5) Uani 1 1 d . . . . .
N1 N 0.48996(15) 0.4402(3) 0.73876(12) 0.0296(5) Uani 1 1 d . . . . .
N2 N 0.44791(15) 0.4755(3) 0.61778(12) 0.0323(5) Uani 1 1 d . . . . .
H2 H 0.415784 0.502143 0.570616 0.039 Uiso 1 1 calc R . . . .
O1 O 0.73472(11) 0.10934(17) 1.18389(9) 0.0187(3) Uani 1 1 d . . . . .
O2 O 0.77382(11) -0.12530(19) 0.88921(9) 0.0223(3) Uani 1 1 d . . . . .
O3 O 0.80805(14) -0.3512(2) 0.95203(10) 0.0338(4) Uani 1 1 d . . . . .
O4 O 0.96663(10) -0.13528(18) 0.95115(8) 0.0182(3) Uani 1 1 d . . . . .
O5 O 0.93768(11) 0.1896(2) 1.09901(9) 0.0249(4) Uani 1 1 d . . . . .
O6 O 0.90911(12) 0.1398(2) 0.85507(9) 0.0281(4) Uani 1 1 d . . . . .
O7 O 0.76550(12) 0.1949(2) 0.82558(9) 0.0260(4) Uani 1 1 d . . . . .
O8 O 0.73222(11) 0.1544(2) 0.97589(9) 0.0261(4) Uani 1 1 d . . . . .
O9 O 0.63288(14) 0.0943(3) 1.02251(12) 0.0384(6) Uani 1 1 d . . . . .
O1W O 0.90305(15) 0.3817(2) 0.96240(11) 0.0353(4) Uani 1 1 d . . . . .
H1WA H 0.871884 0.458683 0.966763 0.042 Uiso 1 1 d R . . . .
H1WB H 0.915304 0.406163 0.924593 0.042 Uiso 1 1 d R . . . .
O2W O 0.88754(15) -0.1235(2) 1.06228(11) 0.0334(4) Uani 1 1 d . . . . .
H2WA H 0.936810 -0.153736 1.099084 0.040 Uiso 1 1 d R . . . .
H2WB H 0.865020 -0.206586 1.036594 0.040 Uiso 1 1 d R . . . .
C1 C 0.80269(15) -0.2636(3) 0.89853(13) 0.0202(4) Uani 1 1 d . . . . .
C2 C 0.83185(15) -0.3319(2) 0.83992(12) 0.0160(4) Uani 1 1 d . . . . .
C3 C 0.77202(16) -0.4322(3) 0.78539(13) 0.0191(4) Uani 1 1 d . . . . .
H3 H 0.713336 -0.446404 0.782385 0.023 Uiso 1 1 calc R . . . .
C4 C 0.79869(15) 0.0115(2) 1.23544(11) 0.0162(4) Uani 1 1 d . . . . .
C5 C 0.88377(16) -0.4899(3) 0.73722(13) 0.0226(5) Uani 1 1 d . . . . .
H5 H 0.901285 -0.543556 0.703111 0.027 Uiso 1 1 calc R . . . .
C6 C 0.94291(17) -0.3872(3) 0.79054(14) 0.0220(5) Uani 1 1 d . . . . .
H6 H 1.000719 -0.370835 0.791959 0.026 Uiso 1 1 calc R . . . .
C7 C 0.91781(15) -0.3076(2) 0.84231(12) 0.0161(4) Uani 1 1 d . . . . .
C8 C 0.98590(15) -0.2036(2) 0.90052(12) 0.0166(4) Uani 1 1 d . . . . .
C9 C 0.82855(16) 0.1644(3) 0.80608(12) 0.0209(4) Uani 1 1 d . . . . .
C10 C 0.80919(16) 0.3577(3) 1.22323(12) 0.0198(4) Uani 1 1 d . . . . .
C11 C 0.8359(2) 0.4988(3) 1.20325(15) 0.0294(5) Uani 1 1 d . . . . .
H11 H 0.866731 0.572357 1.241383 0.035 Uiso 1 1 calc R . . . .
C12 C 0.8176(2) 0.5319(3) 1.12759(15) 0.0328(6) Uani 1 1 d . . . . .
H12 H 0.833949 0.628572 1.114337 0.039 Uiso 1 1 calc R . . . .
C13 C 0.77512(19) 0.4216(3) 1.07232(14) 0.0253(5) Uani 1 1 d . . . . .
H13 H 0.764858 0.442600 1.021539 0.030 Uiso 1 1 calc R . . . .
C14 C 0.74705(15) 0.2798(3) 1.08980(12) 0.0176(4) Uani 1 1 d . . . . .
C15 C 0.76438(14) 0.2491(2) 1.16604(11) 0.0156(4) Uani 1 1 d . . . . .
C16 C 0.70027(15) 0.1659(3) 1.02592(12) 0.0209(4) Uani 1 1 d . . . . .
C17 C 0.4217(3) 0.4056(6) 0.8284(2) 0.0738(16) Uani 1 1 d . . . . .
H17 H 0.370765 0.360164 0.789323 0.089 Uiso 1 1 calc R . . . .
C18 C 0.4251(3) 0.4239(6) 0.9016(2) 0.0830(18) Uani 1 1 d . . . . .
H18 H 0.375706 0.390184 0.910923 0.100 Uiso 1 1 calc R . . . .
C19 C 0.4984(2) 0.4896(4) 0.96054(15) 0.0395(7) Uani 1 1 d . . . . .
C20 C 0.5680(2) 0.5421(4) 0.94370(16) 0.0451(7) Uani 1 1 d . . . . .
H20 H 0.617983 0.591455 0.981963 0.054 Uiso 1 1 calc R . . . .
C21 C 0.5661(2) 0.5238(5) 0.87141(16) 0.0458(8) Uani 1 1 d . . . . .
H21 H 0.614864 0.558921 0.861562 0.055 Uiso 1 1 calc R . . . .
C22 C 0.49290(18) 0.4543(4) 0.81431(14) 0.0325(6) Uani 1 1 d . . . . .
C23 C 0.55838(18) 0.3831(3) 0.72062(15) 0.0289(5) Uani 1 1 d . . . . .
H23 H 0.612879 0.337241 0.754435 0.035 Uiso 1 1 calc R . . . .
C24 C 0.53147(19) 0.4064(3) 0.64476(16) 0.0322(6) Uani 1 1 d . . . . .
H24 H 0.563991 0.380050 0.616038 0.039 Uiso 1 1 calc R . . . .
C25 C 0.42390(18) 0.4954(4) 0.67456(15) 0.0341(6) Uani 1 1 d . . . . .
H25 H 0.369552 0.540632 0.670693 0.041 Uiso 1 1 calc R . . . .


_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
Pr1 O2 2.3986(17) . ?
Pr1 O4 2.5731(16) . ?
Pr1 O4 2.5317(17) 3_757 ?
Pr1 O5 2.5075(17) . ?
Pr1 O6 2.4755(18) . ?
Pr1 O7 2.6024(18) . ?
Pr1 O8 2.3324(17) . ?
Pr1 O1W 2.563(2) . ?
Pr1 O2W 2.5314(19) . ?
Pr1 C8 2.867(2) 3_757 ?
N1 C22 1.428(3) . ?
N1 C23 1.374(3) . ?
N1 C25 1.328(3) . ?
N2 H2 0.8600 . ?
N2 C24 1.357(4) . ?
N2 C25 1.305(3) . ?
O1 C4 1.369(2) . ?
O1 C15 1.376(2) . ?
O2 C1 1.250(3) . ?
O3 C1 1.237(3) . ?
O4 C8 1.272(2) . ?
O5 C8 1.232(3) 3_757 ?
O6 C9 1.259(3) . ?
O7 C9 1.246(3) . ?
O8 C16 1.264(3) . ?
O9 C16 1.222(3) . ?
O1W H1WA 0.8501 . ?
O1W H1WB 0.8498 . ?
O2W H2WA 0.8500 . ?
O2W H2WB 0.8500 . ?
C1 C2 1.500(3) . ?
C2 C3 1.378(3) . ?
C2 C7 1.381(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.375(3) 4 ?
C4 C5 1.368(3) 4_556 ?
C5 H5 0.9300 . ?
C5 C6 1.376(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.390(3) . ?
C7 C8 1.483(3) . ?
C9 C10 1.490(3) 4_565 ?
C10 C11 1.381(3) . ?
C10 C15 1.381(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.377(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.363(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.377(3) . ?
C14 C15 1.387(3) . ?
C14 C16 1.491(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.384(5) . ?
C17 C22 1.348(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.363(5) . ?
C19 C19 1.496(5) 3_667 ?
C19 C20 1.365(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.376(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.360(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.341(4) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Pr1 O4 69.09(6) . . ?
O2 Pr1 O4 136.70(5) . 3_757 ?
O2 Pr1 O5 140.53(6) . . ?
O2 Pr1 O6 87.85(6) . . ?
O2 Pr1 O7 72.49(6) . . ?
O2 Pr1 O1W 145.33(6) . . ?
O2 Pr1 O2W 75.91(6) . . ?
O2 Pr1 C8 150.14(6) . 3_757 ?
O4 Pr1 O4 68.47(6) 3_757 . ?
O4 Pr1 O7 129.94(5) 3_757 . ?
O4 Pr1 O7 108.39(5) . . ?
O4 Pr1 O1W 70.37(6) 3_757 . ?
O4 Pr1 C8 26.33(5) 3_757 3_757 ?
O4 Pr1 C8 90.98(6) . 3_757 ?
O5 Pr1 O4 51.17(5) . 3_757 ?
O5 Pr1 O4 108.08(5) . . ?
O5 Pr1 O7 138.42(6) . . ?
O5 Pr1 O1W 70.48(6) . . ?
O5 Pr1 O2W 67.11(6) . . ?
O5 Pr1 C8 25.39(6) . 3_757 ?
O6 Pr1 O4 85.23(6) . 3_757 ?
O6 Pr1 O4 69.42(6) . . ?
O6 Pr1 O5 129.31(6) . . ?
O6 Pr1 O7 51.00(6) . . ?
O6 Pr1 O1W 71.19(6) . . ?
O6 Pr1 O2W 138.52(6) . . ?
O6 Pr1 C8 106.24(7) . 3_757 ?
O7 Pr1 C8 136.68(6) . 3_757 ?
O8 Pr1 O2 82.69(6) . . ?
O8 Pr1 O4 146.06(6) . . ?
O8 Pr1 O4 132.44(6) . 3_757 ?
O8 Pr1 O5 81.75(6) . . ?
O8 Pr1 O6 129.64(6) . . ?
O8 Pr1 O7 79.13(6) . . ?
O8 Pr1 O1W 89.75(7) . . ?
O8 Pr1 O2W 86.39(7) . . ?
O8 Pr1 C8 106.11(6) . 3_757 ?
O1W Pr1 O4 124.19(6) . . ?
O1W Pr1 O7 72.86(6) . . ?
O1W Pr1 C8 64.32(6) . 3_757 ?
O2W Pr1 O4 69.14(6) . . ?
O2W Pr1 O4 81.49(6) . 3_757 ?
O2W Pr1 O7 146.58(6) . . ?
O2W Pr1 O1W 137.53(6) . . ?
O2W Pr1 C8 76.26(7) . 3_757 ?
C23 N1 C22 126.4(2) . . ?
C25 N1 C22 125.3(2) . . ?
C25 N1 C23 108.0(2) . . ?
C24 N2 H2 125.3 . . ?
C25 N2 H2 125.3 . . ?
C25 N2 C24 109.4(2) . . ?
C4 O1 C15 117.94(17) . . ?
C1 O2 Pr1 121.94(14) . . ?
Pr1 O4 Pr1 111.53(6) 3_757 . ?
C8 O4 Pr1 91.73(13) . 3_757 ?
C8 O4 Pr1 140.24(13) . . ?
C8 O5 Pr1 93.86(13) 3_757 . ?
C9 O6 Pr1 94.99(14) . . ?
C9 O7 Pr1 89.39(13) . . ?
C16 O8 Pr1 141.47(15) . . ?
Pr1 O1W H1WA 126.8 . . ?
Pr1 O1W H1WB 112.4 . . ?
H1WA O1W H1WB 104.5 . . ?
Pr1 O2W H2WA 128.5 . . ?
Pr1 O2W H2WB 105.6 . . ?
H2WA O2W H2WB 104.5 . . ?
O2 C1 C2 118.2(2) . . ?
O3 C1 O2 125.3(2) . . ?
O3 C1 C2 116.6(2) . . ?
C3 C2 C1 117.72(19) . . ?
C3 C2 C7 119.45(19) . . ?
C7 C2 C1 122.64(19) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.3(2) 4 . ?
C4 C3 H3 119.8 4 . ?
O1 C4 C3 115.9(2) . 4_556 ?
C5 C4 O1 122.94(19) 4_556 . ?
C5 C4 C3 121.1(2) 4_556 4_556 ?
C4 C5 H5 120.7 4 . ?
C4 C5 C6 118.6(2) 4 . ?
C6 C5 H5 120.7 . . ?
C5 C6 H6 119.4 . . ?
C5 C6 C7 121.2(2) . . ?
C7 C6 H6 119.4 . . ?
C2 C7 C6 119.3(2) . . ?
C2 C7 C8 122.04(19) . . ?
C6 C7 C8 118.7(2) . . ?
O4 C8 Pr1 61.94(11) . 3_757 ?
O4 C8 C7 120.19(19) . . ?
O5 C8 Pr1 60.75(11) 3_757 3_757 ?
O5 C8 O4 120.66(19) 3_757 . ?
O5 C8 C7 119.08(19) 3_757 . ?
C7 C8 Pr1 163.07(14) . 3_757 ?
O6 C9 C10 117.4(2) . 4_565 ?
O7 C9 O6 121.8(2) . . ?
O7 C9 C10 120.6(2) . 4_565 ?
C11 C10 C9 116.9(2) . 4_566 ?
C11 C10 C15 118.9(2) . . ?
C15 C10 C9 124.2(2) . 4_566 ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.8(2) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.3(2) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 H13 119.2 . . ?
C12 C13 C14 121.6(2) . . ?
C14 C13 H13 119.2 . . ?
C13 C14 C15 118.5(2) . . ?
C13 C14 C16 118.37(19) . . ?
C15 C14 C16 123.2(2) . . ?
O1 C15 C10 120.18(18) . . ?
O1 C15 C14 118.95(19) . . ?
C10 C15 C14 120.9(2) . . ?
O8 C16 C14 116.3(2) . . ?
O9 C16 O8 123.6(2) . . ?
O9 C16 C14 120.1(2) . . ?
C18 C17 H17 120.4 . . ?
C22 C17 H17 120.4 . . ?
C22 C17 C18 119.2(3) . . ?
C17 C18 H18 118.8 . . ?
C19 C18 C17 122.3(3) . . ?
C19 C18 H18 118.8 . . ?
C18 C19 C19 122.3(4) . 3_667 ?
C18 C19 C20 116.9(3) . . ?
C20 C19 C19 120.8(3) . 3_667 ?
C19 C20 H20 119.2 . . ?
C19 C20 C21 121.5(3) . . ?
C21 C20 H20 119.2 . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.1(3) . . ?
C22 C21 H21 119.9 . . ?
C17 C22 N1 120.3(3) . . ?
C17 C22 C21 119.9(3) . . ?
C21 C22 N1 119.8(3) . . ?
N1 C23 H23 126.6 . . ?
C24 C23 N1 106.8(2) . . ?
C24 C23 H23 126.6 . . ?
N2 C24 H24 126.4 . . ?
C23 C24 N2 107.2(2) . . ?
C23 C24 H24 126.4 . . ?
N1 C25 H25 125.7 . . ?
N2 C25 N1 108.6(2) . . ?
N2 C25 H25 125.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1W H1WA O3 0.85 1.87 2.699(3) 163.7 1_565 yes
O1W H1WB O6 0.85 2.61 2.933(3) 104.3 . yes
O2W H2WA O6 0.85 2.26 2.984(3) 142.8 3_757 yes
O2W H2WB O3 0.85 1.93 2.750(3) 162.1 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Pr1 O2 C1 O3 77.8(3) . . . . ?
Pr1 O2 C1 C2 -103.4(2) . . . . ?
Pr1 O4 C8 Pr1 127.6(2) . . . 3_757 ?
Pr1 O4 C8 O5 111.3(2) . . . 3_757 ?
Pr1 O4 C8 O5 -16.3(2) 3_757 . . 3_757 ?
Pr1 O4 C8 C7 160.75(17) 3_757 . . . ?
Pr1 O4 C8 C7 -71.6(3) . . . . ?
Pr1 O6 C9 O7 17.7(2) . . . . ?
Pr1 O6 C9 C10 -157.19(18) . . . 4_565 ?
Pr1 O7 C9 O6 -16.8(2) . . . . ?
Pr1 O7 C9 C10 157.99(19) . . . 4_565 ?
Pr1 O8 C16 O9 -122.6(3) . . . . ?
Pr1 O8 C16 C14 60.2(3) . . . . ?
N1 C23 C24 N2 -0.3(3) . . . . ?
O2 C1 C2 C3 -101.4(2) . . . . ?
O2 C1 C2 C7 83.6(3) . . . . ?
O3 C1 C2 C3 77.5(3) . . . . ?
O3 C1 C2 C7 -97.5(3) . . . . ?
C1 C2 C3 C4 -173.0(2) . . . 4 ?
C1 C2 C7 C6 173.7(2) . . . . ?
C1 C2 C7 C8 -3.9(3) . . . . ?
C2 C7 C8 Pr1 93.5(5) . . . 3_757 ?
C2 C7 C8 O4 1.1(3) . . . . ?
C2 C7 C8 O5 178.2(2) . . . 3_757 ?
C3 C2 C7 C6 -1.2(3) . . . . ?
C3 C2 C7 C8 -178.8(2) . . . . ?
C4 O1 C15 C10 -59.8(3) . . . . ?
C4 O1 C15 C14 121.4(2) . . . . ?
C4 C5 C6 C7 0.6(4) 4 . . . ?
C5 C6 C7 C2 -0.2(3) . . . . ?
C5 C6 C7 C8 177.5(2) . . . . ?
C6 C7 C8 Pr1 -84.0(5) . . . 3_757 ?
C6 C7 C8 O4 -176.5(2) . . . . ?
C6 C7 C8 O5 0.6(3) . . . 3_757 ?
C7 C2 C3 C4 2.1(3) . . . 4 ?
C9 C10 C11 C12 -177.4(3) 4_566 . . . ?
C9 C10 C15 O1 -0.3(3) 4_566 . . . ?
C9 C10 C15 C14 178.5(2) 4_566 . . . ?
C10 C11 C12 C13 -2.2(4) . . . . ?
C11 C10 C15 O1 -178.2(2) . . . . ?
C11 C10 C15 C14 0.6(3) . . . . ?
C11 C12 C13 C14 2.4(4) . . . . ?
C12 C13 C14 C15 -1.2(4) . . . . ?
C12 C13 C14 C16 179.4(2) . . . . ?
C13 C14 C15 O1 178.5(2) . . . . ?
C13 C14 C15 C10 -0.4(3) . . . . ?
C13 C14 C16 O8 40.1(3) . . . . ?
C13 C14 C16 O9 -137.3(3) . . . . ?
C15 O1 C4 C3 142.7(2) . . . 4_556 ?
C15 O1 C4 C5 -38.5(3) . . . 4_556 ?
C15 C10 C11 C12 0.7(4) . . . . ?
C15 C14 C16 O8 -139.3(2) . . . . ?
C15 C14 C16 O9 43.3(3) . . . . ?
C16 C14 C15 O1 -2.1(3) . . . . ?
C16 C14 C15 C10 179.0(2) . . . . ?
C17 C18 C19 C19 179.5(5) . . . 3_667 ?
C17 C18 C19 C20 2.1(7) . . . . ?
C18 C17 C22 N1 -178.4(4) . . . . ?
C18 C17 C22 C21 -1.5(7) . . . . ?
C18 C19 C20 C21 -2.6(6) . . . . ?
C19 C19 C20 C21 180.0(4) 3_667 . . . ?
C19 C20 C21 C22 1.1(6) . . . . ?
C20 C21 C22 N1 178.0(3) . . . . ?
C20 C21 C22 C17 1.0(6) . . . . ?
C22 N1 C23 C24 -173.4(3) . . . . ?
C22 N1 C25 N2 173.7(3) . . . . ?
C22 C17 C18 C19 -0.1(8) . . . . ?
C23 N1 C22 C17 -133.8(4) . . . . ?
C23 N1 C22 C21 49.2(4) . . . . ?
C23 N1 C25 N2 0.0(3) . . . . ?
C24 N2 C25 N1 -0.2(3) . . . . ?
C25 N1 C22 C17 53.6(5) . . . . ?
C25 N1 C22 C21 -123.4(3) . . . . ?
C25 N1 C23 C24 0.2(3) . . . . ?
C25 N2 C24 C23 0.3(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_108331
_database_code_depnum_ccdc_archive 'CCDC 1835488'
loop_
_audit_author_name
_audit_author_address
Lirongyang
;Henan University
China
;
_audit_update_record             
;
2020-08-14 deposited with the CCDC.	2020-08-19 downloaded from the CCDC.
;
_audit_creation_date             2020-08-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H10 Eu O11, C9 H8 N2'
_chemical_formula_sum            'C25 H18 Eu N2 O11'
_chemical_formula_weight         674.37
_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.213(3)
_cell_length_b                   8.5404(14)
_cell_length_c                   19.151(4)
_cell_angle_alpha                90
_cell_angle_beta                 114.685(3)
_cell_angle_gamma                90
_cell_volume                     2409.4(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    651
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      16.82
_cell_measurement_theta_min      2.66
_shelx_estimated_absorpt_T_max   0.878
_shelx_estimated_absorpt_T_min   0.815
_exptl_absorpt_coefficient_mu    2.672
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0920 before and 0.0715 after correction. The Ratio of minimum to maximum transmission is 0.8215. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.859
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1332
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1233
_diffrn_reflns_av_unetI/netI     0.1691
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            14806
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.191
_diffrn_reflns_theta_min         2.165
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker Smart APEX II CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3187
_reflns_number_total             5796
_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       'APEX 2'
_computing_data_collection       'APEX 2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.384
_refine_diff_density_min         -1.467
_refine_diff_density_rms         0.229
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         5796
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1330
_refine_ls_R_factor_gt           0.0600
_refine_ls_restrained_S_all      0.942
_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)+(0.0330P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1291
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
O9 \\sim C25 \\sim O8: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(C8) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Rotating group:
 O1W(H1WA,H1WB), O2W(H2WA,H2WB)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C3(H3), C9(H9), C8(H8), C6(H6), C5(H5), C12(H12),
 C13(H13), C14(H14), C20(H20), C21(H21), C23(H23)
3.c Fitted hexagon refined as free rotating group:
 C4(C9,C8,C7,C6,C5)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Eu1 Eu 0.13320(3) 0.58745(5) 0.03610(2) 0.01831(13) Uani 1 1 d . . . . .
N1 N 0.4475(5) 0.4749(9) 0.1173(5) 0.037(2) Uani 1 1 d . . . . .
H1 H 0.415933 0.502331 0.070365 0.044 Uiso 1 1 calc R . . . .
N2 N 0.4886(5) 0.4388(10) 0.2378(4) 0.033(2) Uani 1 1 d . . . . .
O1 O 0.2626(4) 0.8486(7) 0.5218(3) 0.0270(15) Uani 1 1 d . . . . .
O2 O 0.3637(4) 0.9091(9) 0.4763(3) 0.0442(19) Uani 1 1 d . . . . .
O3 O 0.2640(4) 0.8897(7) 0.3140(3) 0.0249(14) Uani 1 1 d . . . . .
O4 O 0.2346(4) 0.6892(7) 0.1717(3) 0.0272(15) Uani 1 1 d . . . . .
O5 O 0.0921(4) 0.6336(7) 0.1431(4) 0.0328(17) Uani 1 1 d . . . . .
O6 O -0.0313(4) 0.6360(7) -0.0451(3) 0.0239(14) Uani 1 1 d . . . . .
O7 O 0.0641(4) 0.6910(7) -0.0959(3) 0.0295(16) Uani 1 1 d . . . . .
O8 O -0.1929(5) 0.8503(7) -0.0463(4) 0.0404(18) Uani 1 1 d . U . . .
O9 O -0.2225(4) 0.6224(6) -0.1082(3) 0.0210(14) Uani 1 1 d . U . . .
O1W O 0.1034(4) 0.8758(7) 0.0407(4) 0.0363(17) Uani 1 1 d . . . . .
H1WA H 0.093032 0.894909 0.080362 0.054 Uiso 1 1 d GR . . . .
H1WB H 0.053610 0.901236 0.002652 0.054 Uiso 1 1 d GR . . . .
O2W O 0.1130(4) 0.3811(7) -0.0614(3) 0.0366(17) Uani 1 1 d . . . . .
H2WA H 0.054418 0.364115 -0.091586 0.055 Uiso 1 1 d GR . . . .
H2WB H 0.131199 0.288022 -0.038931 0.055 Uiso 1 1 d GR . . . .
C1 C 0.4227(6) 0.4956(12) 0.1743(5) 0.034(3) Uani 1 1 d . . . . .
H1A H 0.368997 0.541494 0.170643 0.041 Uiso 1 1 calc R . . . .
C2 C 0.5299(6) 0.4040(13) 0.1436(5) 0.036(2) Uani 1 1 d . . . . .
H2 H 0.561440 0.376217 0.114556 0.043 Uiso 1 1 calc R . . . .
C3 C 0.5576(6) 0.3814(12) 0.2198(5) 0.033(3) Uani 1 1 d . . . . .
H3 H 0.611965 0.336465 0.253494 0.040 Uiso 1 1 calc R . . . .
C4 C 0.4923(4) 0.4533(9) 0.3137(3) 0.039(3) Uani 1 1 d . . . . .
C9 C 0.4209(4) 0.4002(10) 0.3295(3) 0.082(5) Uani 1 1 d G . . . .
H9 H 0.370968 0.352445 0.291134 0.099 Uiso 1 1 calc R . . . .
C8 C 0.4240(4) 0.4186(10) 0.4027(4) 0.075(4) Uani 1 1 d G U . . .
H8 H 0.376217 0.383048 0.413294 0.090 Uiso 1 1 calc R . . . .
C7 C 0.4986(5) 0.4900(10) 0.4601(3) 0.046(3) Uani 1 1 d G . . . .
C6 C 0.5701(4) 0.5431(9) 0.4443(3) 0.058(4) Uani 1 1 d G . . . .
H6 H 0.619965 0.590888 0.482666 0.070 Uiso 1 1 calc R . . . .
C5 C 0.5669(4) 0.5248(9) 0.3711(4) 0.054(3) Uani 1 1 d G . . . .
H5 H 0.614717 0.560286 0.360507 0.064 Uiso 1 1 calc R . . . .
C10 C 0.1724(6) 0.6598(10) 0.1923(5) 0.024(2) Uani 1 1 d . . . . .
C11 C 0.1904(6) 0.6380(10) 0.2751(5) 0.022(2) Uani 1 1 d . . . . .
C12 C 0.1658(6) 0.4984(10) 0.2963(5) 0.028(2) Uani 1 1 d . . . . .
H12 H 0.137464 0.423228 0.258683 0.033 Uiso 1 1 calc R . . . .
C13 C 0.1819(7) 0.4652(11) 0.3719(5) 0.037(3) Uani 1 1 d . . . . .
H13 H 0.165278 0.369297 0.385151 0.045 Uiso 1 1 calc R . . . .
C14 C 0.2228(6) 0.5772(12) 0.4260(5) 0.033(2) Uani 1 1 d . . . . .
H14 H 0.232377 0.556920 0.476559 0.040 Uiso 1 1 calc R . . . .
C15 C 0.2510(6) 0.7214(11) 0.4090(4) 0.022(2) Uani 1 1 d . . . . .
C16 C 0.2347(5) 0.7494(11) 0.3323(5) 0.0208(19) Uani 1 1 d . . . . .
C17 C 0.2960(6) 0.8387(11) 0.4729(5) 0.026(2) Uani 1 1 d . . . . .
C18 C -0.0131(6) 0.7058(10) -0.0975(5) 0.022(2) Uani 1 1 d . . . . .
C19 C -0.0806(5) 0.8068(9) -0.1551(4) 0.0142(18) Uani 1 1 d . . . . .
C20 C -0.0552(6) 0.8866(10) -0.2060(5) 0.024(2) Uani 1 1 d . . . . .
H20 H 0.002375 0.870074 -0.204190 0.029 Uiso 1 1 calc R . . . .
C21 C -0.1145(6) 0.9924(10) -0.2603(5) 0.025(2) Uani 1 1 d . . . . .
H21 H -0.096822 1.045848 -0.294155 0.030 Uiso 1 1 calc R . . . .
C22 C -0.1996(6) 1.0143(10) -0.2618(5) 0.025(2) Uani 1 1 d . . . . .
C23 C -0.2265(5) 0.9318(10) -0.2123(5) 0.0209(19) Uani 1 1 d . . . . .
H23 H -0.284883 0.944335 -0.215438 0.025 Uiso 1 1 calc R . . . .
C24 C -0.1666(5) 0.8315(10) -0.1586(5) 0.0196(19) Uani 1 1 d . . . . .
C25 C -0.1961(6) 0.7622(11) -0.0994(5) 0.024(2) Uani 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Eu1 Eu1 4.2201(11) 3_565 ?
Eu1 O1 2.293(6) 4_575 ?
Eu1 O4 2.576(6) . ?
Eu1 O5 2.437(6) . ?
Eu1 O6 2.497(5) . ?
Eu1 O6 2.576(5) 3_565 ?
Eu1 O7 2.463(6) . ?
Eu1 O9 2.355(5) 3_565 ?
Eu1 O1W 2.518(6) . ?
Eu1 O2W 2.487(6) . ?
Eu1 C25 3.224(9) 3_565 ?
N1 H1 0.8600 . ?
N1 C1 1.323(11) . ?
N1 C2 1.359(11) . ?
N2 C1 1.331(10) . ?
N2 C3 1.391(11) . ?
N2 C4 1.435(8) . ?
O1 C17 1.265(10) . ?
O2 C17 1.229(10) . ?
O3 C16 1.387(10) . ?
O3 C22 1.376(9) 3_575 ?
O4 C10 1.252(10) . ?
O5 C10 1.268(10) . ?
O6 C18 1.303(10) . ?
O7 C18 1.246(9) . ?
O8 C25 1.249(10) . ?
O9 C25 1.256(10) . ?
O1W H1WA 0.8590 . ?
O1W H1WB 0.8591 . ?
O2W H2WA 0.8945 . ?
O2W H2WB 0.8927 . ?
C1 H1A 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.349(11) . ?
C3 H3 0.9300 . ?
C4 C9 1.3900 . ?
C4 C5 1.3900 . ?
C9 H9 0.9300 . ?
C9 C8 1.3900 . ?
C8 H8 0.9300 . ?
C8 C7 1.3900 . ?
C7 C7 1.520(9) 3_666 ?
C7 C6 1.3900 . ?
C6 H6 0.9300 . ?
C6 C5 1.3900 . ?
C5 H5 0.9300 . ?
C10 C11 1.500(11) . ?
C11 C12 1.371(11) . ?
C11 C16 1.401(11) . ?
C12 H12 0.9300 . ?
C12 C13 1.389(12) . ?
C13 H13 0.9300 . ?
C13 C14 1.362(12) . ?
C14 H14 0.9300 . ?
C14 C15 1.399(12) . ?
C15 C16 1.399(10) . ?
C15 C17 1.513(11) . ?
C18 C19 1.467(11) . ?
C19 C20 1.385(11) . ?
C19 C24 1.384(10) . ?
C20 H20 0.9300 . ?
C20 C21 1.410(11) . ?
C21 H21 0.9300 . ?
C21 C22 1.382(11) . ?
C22 C23 1.388(11) . ?
C23 H23 0.9300 . ?
C23 C24 1.379(11) . ?
C24 C25 1.521(11) . ?

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 155.19(14) 4_575 3_565 ?
O1 Eu1 O4 79.03(19) 4_575 . ?
O1 Eu1 O5 130.3(2) 4_575 . ?
O1 Eu1 O6 146.0(2) 4_575 3_565 ?
O1 Eu1 O6 132.75(19) 4_575 . ?
O1 Eu1 O7 80.68(19) 4_575 . ?
O1 Eu1 O9 83.2(2) 4_575 3_565 ?
O1 Eu1 O1W 88.3(2) 4_575 . ?
O1 Eu1 O2W 85.4(2) 4_575 . ?
O1 Eu1 C25 96.0(2) 4_575 3_565 ?
O4 Eu1 Eu1 125.77(14) . 3_565 ?
O4 Eu1 O6 109.85(18) . 3_565 ?
O4 Eu1 C25 88.0(2) . 3_565 ?
O5 Eu1 Eu1 74.39(14) . 3_565 ?
O5 Eu1 O4 51.76(19) . . ?
O5 Eu1 O6 84.3(2) . . ?
O5 Eu1 O6 69.85(19) . 3_565 ?
O5 Eu1 O7 129.7(2) . . ?
O5 Eu1 O1W 71.8(2) . . ?
O5 Eu1 O2W 138.5(2) . . ?
O5 Eu1 C25 89.3(2) . 3_565 ?
O6 Eu1 Eu1 34.32(13) . 3_565 ?
O6 Eu1 Eu1 33.12(12) 3_565 3_565 ?
O6 Eu1 O4 129.60(19) . . ?
O6 Eu1 O6 67.4(2) . 3_565 ?
O6 Eu1 O1W 71.86(19) . . ?
O6 Eu1 C25 53.1(2) 3_565 3_565 ?
O6 Eu1 C25 118.4(2) . 3_565 ?
O7 Eu1 Eu1 80.01(14) . 3_565 ?
O7 Eu1 O4 137.7(2) . . ?
O7 Eu1 O6 107.76(19) . 3_565 ?
O7 Eu1 O6 52.55(18) . . ?
O7 Eu1 O1W 70.9(2) . . ?
O7 Eu1 O2W 67.9(2) . . ?
O7 Eu1 C25 131.0(2) . 3_565 ?
O9 Eu1 Eu1 102.55(13) 3_565 3_565 ?
O9 Eu1 O4 71.85(19) 3_565 . ?
O9 Eu1 O5 87.0(2) 3_565 . ?
O9 Eu1 O6 136.60(18) 3_565 . ?
O9 Eu1 O6 69.63(18) 3_565 3_565 ?
O9 Eu1 O7 141.2(2) 3_565 . ?
O9 Eu1 O1W 143.5(2) 3_565 . ?
O9 Eu1 O2W 75.9(2) 3_565 . ?
O9 Eu1 C25 18.9(2) 3_565 3_565 ?
O1W Eu1 Eu1 99.92(14) . 3_565 ?
O1W Eu1 O4 71.69(19) . . ?
O1W Eu1 O6 125.72(19) . 3_565 ?
O1W Eu1 C25 158.1(2) . 3_565 ?
O2W Eu1 Eu1 73.00(15) . 3_565 ?
O2W Eu1 O4 145.5(2) . . ?
O2W Eu1 O6 68.79(19) . 3_565 ?
O2W Eu1 O6 83.1(2) . . ?
O2W Eu1 O1W 138.8(2) . . ?
O2W Eu1 C25 63.1(2) . 3_565 ?
C25 Eu1 Eu1 85.12(16) 3_565 3_565 ?
C1 N1 H1 124.9 . . ?
C1 N1 C2 110.1(8) . . ?
C2 N1 H1 124.9 . . ?
C1 N2 C3 108.9(8) . . ?
C1 N2 C4 124.9(8) . . ?
C3 N2 C4 125.7(7) . . ?
C17 O1 Eu1 143.1(5) . 4_576 ?
C22 O3 C16 117.6(6) 3_575 . ?
C10 O4 Eu1 89.5(5) . . ?
C10 O5 Eu1 95.6(5) . . ?
Eu1 O6 Eu1 112.6(2) . 3_565 ?
C18 O6 Eu1 91.7(5) . . ?
C18 O6 Eu1 138.4(5) . 3_565 ?
C18 O7 Eu1 94.7(5) . . ?
C25 O9 Eu1 123.6(5) . 3_565 ?
Eu1 O1W H1WA 109.2 . . ?
Eu1 O1W H1WB 110.1 . . ?
H1WA O1W H1WB 103.9 . . ?
Eu1 O2W H2WA 111.8 . . ?
Eu1 O2W H2WB 110.9 . . ?
H2WA O2W H2WB 102.4 . . ?
N1 C1 N2 107.5(8) . . ?
N1 C1 H1A 126.2 . . ?
N2 C1 H1A 126.2 . . ?
N1 C2 H2 126.4 . . ?
C3 C2 N1 107.3(8) . . ?
C3 C2 H2 126.4 . . ?
N2 C3 H3 126.9 . . ?
C2 C3 N2 106.2(8) . . ?
C2 C3 H3 126.9 . . ?
C9 C4 N2 120.4(5) . . ?
C9 C4 C5 120.0 . . ?
C5 C4 N2 119.6(5) . . ?
C4 C9 H9 120.0 . . ?
C8 C9 C4 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C8 H8 120.0 . . ?
C9 C8 C7 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C7 C7 119.7(9) . 3_666 ?
C6 C7 C8 120.0 . . ?
C6 C7 C7 120.3(9) . 3_666 ?
C7 C6 H6 120.0 . . ?
C5 C6 C7 120.0 . . ?
C5 C6 H6 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.0 . . ?
C6 C5 H5 120.0 . . ?
O4 C10 O5 120.9(8) . . ?
O4 C10 C11 122.1(8) . . ?
O5 C10 C11 116.7(8) . . ?
C12 C11 C10 117.9(8) . . ?
C12 C11 C16 118.5(8) . . ?
C16 C11 C10 123.5(8) . . ?
C11 C12 H12 118.9 . . ?
C11 C12 C13 122.3(9) . . ?
C13 C12 H12 118.9 . . ?
C12 C13 H13 121.0 . . ?
C14 C13 C12 118.0(9) . . ?
C14 C13 H13 121.0 . . ?
C13 C14 H14 118.6 . . ?
C13 C14 C15 122.9(8) . . ?
C15 C14 H14 118.6 . . ?
C14 C15 C17 119.2(8) . . ?
C16 C15 C14 117.3(8) . . ?
C16 C15 C17 123.5(8) . . ?
O3 C16 C11 120.5(7) . . ?
O3 C16 C15 118.5(8) . . ?
C15 C16 C11 121.0(8) . . ?
O1 C17 C15 115.6(8) . . ?
O2 C17 O1 125.3(9) . . ?
O2 C17 C15 119.0(8) . . ?
O6 C18 C19 120.7(8) . . ?
O7 C18 O6 118.9(8) . . ?
O7 C18 C19 120.3(8) . . ?
C20 C19 C18 118.0(7) . . ?
C24 C19 C18 123.1(8) . . ?
C24 C19 C20 118.8(8) . . ?
C19 C20 H20 119.2 . . ?
C19 C20 C21 121.5(8) . . ?
C21 C20 H20 119.2 . . ?
C20 C21 H21 121.0 . . ?
C22 C21 C20 118.0(8) . . ?
C22 C21 H21 121.0 . . ?
O3 C22 C21 122.9(8) 3_575 . ?
O3 C22 C23 116.1(8) 3_575 . ?
C21 C22 C23 120.9(8) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 120.1(8) . . ?
C24 C23 H23 120.0 . . ?
C19 C24 C25 121.9(7) . . ?
C23 C24 C19 120.7(8) . . ?
C23 C24 C25 117.1(7) . . ?
O8 C25 Eu1 110.7(5) . 3_565 ?
O8 C25 O9 125.3(8) . . ?
O8 C25 C24 117.0(8) . . ?
O9 C25 Eu1 37.5(4) . 3_565 ?
O9 C25 C24 117.8(8) . . ?
C24 C25 Eu1 119.5(5) . 3_565 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1A O4 0.93 2.53 3.451(11) 173.4 . yes
C1 H1A O9 0.93 2.58 3.117(10) 117.2 3_565 yes
C2 H2 O2 0.93 2.52 3.400(10) 158.3 2_645 yes
C2 H2 O3 0.93 2.58 3.093(10) 115.2 2_645 yes
C3 H3 O4 0.93 2.62 3.538(11) 170.7 2_645 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Eu1 O1 C17 O2 121.6(10) 4_576 . . . ?
Eu1 O1 C17 C15 -62.8(13) 4_576 . . . ?
Eu1 O4 C10 O5 -15.0(8) . . . . ?
Eu1 O4 C10 C11 158.8(7) . . . . ?
Eu1 O5 C10 O4 16.0(9) . . . . ?
Eu1 O5 C10 C11 -158.1(6) . . . . ?
Eu1 O6 C18 O7 -113.1(8) 3_565 . . . ?
Eu1 O6 C18 O7 14.6(8) . . . . ?
Eu1 O6 C18 C19 -162.3(7) . . . . ?
Eu1 O6 C18 C19 70.1(11) 3_565 . . . ?
Eu1 O7 C18 O6 -14.9(8) . . . . ?
Eu1 O7 C18 C19 162.0(6) . . . . ?
Eu1 O9 C25 O8 -77.8(10) 3_565 . . . ?
Eu1 O9 C25 C24 103.1(7) 3_565 . . . ?
N1 C2 C3 N2 0.9(11) . . . . ?
N2 C4 C9 C8 -178.3(7) . . . . ?
N2 C4 C5 C6 178.3(7) . . . . ?
O3 C22 C23 C24 179.3(7) 3_575 . . . ?
O4 C10 C11 C12 -121.4(10) . . . . ?
O4 C10 C11 C16 55.4(12) . . . . ?
O5 C10 C11 C12 52.7(11) . . . . ?
O5 C10 C11 C16 -130.6(9) . . . . ?
O6 C18 C19 C20 175.5(7) . . . . ?
O6 C18 C19 C24 -1.4(12) . . . . ?
O7 C18 C19 C20 -1.4(12) . . . . ?
O7 C18 C19 C24 -178.2(8) . . . . ?
C1 N1 C2 C3 -0.6(12) . . . . ?
C1 N2 C3 C2 -0.9(11) . . . . ?
C1 N2 C4 C9 56.0(11) . . . . ?
C1 N2 C4 C5 -122.3(9) . . . . ?
C2 N1 C1 N2 0.1(12) . . . . ?
C3 N2 C1 N1 0.5(11) . . . . ?
C3 N2 C4 C9 -132.6(8) . . . . ?
C3 N2 C4 C5 49.1(11) . . . . ?
C4 N2 C1 N1 173.1(8) . . . . ?
C4 N2 C3 C2 -173.4(9) . . . . ?
C4 C9 C8 C7 0.0 . . . . ?
C9 C4 C5 C6 0.0 . . . . ?
C9 C8 C7 C7 179.8(13) . . . 3_666 ?
C9 C8 C7 C6 0.0 . . . . ?
C8 C7 C6 C5 0.0 . . . . ?
C7 C7 C6 C5 -179.8(13) 3_666 . . . ?
C7 C6 C5 C4 0.0 . . . . ?
C5 C4 C9 C8 0.0 . . . . ?
C10 C11 C12 C13 178.2(8) . . . . ?
C10 C11 C16 O3 0.6(13) . . . . ?
C10 C11 C16 C15 -178.8(8) . . . . ?
C11 C12 C13 C14 0.6(14) . . . . ?
C12 C11 C16 O3 177.4(8) . . . . ?
C12 C11 C16 C15 -2.1(13) . . . . ?
C12 C13 C14 C15 -1.7(14) . . . . ?
C13 C14 C15 C16 0.8(14) . . . . ?
C13 C14 C15 C17 -179.9(8) . . . . ?
C14 C15 C16 O3 -178.4(7) . . . . ?
C14 C15 C16 C11 1.1(12) . . . . ?
C14 C15 C17 O1 -39.4(11) . . . . ?
C14 C15 C17 O2 136.5(9) . . . . ?
C16 C11 C12 C13 1.2(14) . . . . ?
C16 C15 C17 O1 139.8(8) . . . . ?
C16 C15 C17 O2 -44.3(12) . . . . ?
C17 C15 C16 O3 2.4(12) . . . . ?
C17 C15 C16 C11 -178.1(8) . . . . ?
C18 C19 C20 C21 -176.6(8) . . . . ?
C18 C19 C24 C23 177.8(8) . . . . ?
C18 C19 C24 C25 3.6(12) . . . . ?
C19 C20 C21 C22 -0.2(13) . . . . ?
C19 C24 C25 Eu1 -39.2(10) . . . 3_565 ?
C19 C24 C25 O8 98.8(10) . . . . ?
C19 C24 C25 O9 -82.1(10) . . . . ?
C20 C19 C24 C23 0.9(12) . . . . ?
C20 C19 C24 C25 -173.3(8) . . . . ?
C20 C21 C22 O3 -177.7(8) . . . 3_575 ?
C20 C21 C22 C23 -1.4(13) . . . . ?
C21 C22 C23 C24 2.8(13) . . . . ?
C22 O3 C16 C11 59.8(10) 3_575 . . . ?
C22 O3 C16 C15 -120.7(8) 3_575 . . . ?
C22 C23 C24 C19 -2.5(12) . . . . ?
C22 C23 C24 C25 171.9(8) . . . . ?
C23 C24 C25 Eu1 146.4(6) . . . 3_565 ?
C23 C24 C25 O8 -75.6(10) . . . . ?
C23 C24 C25 O9 103.5(9) . . . . ?
C24 C19 C20 C21 0.4(12) . . . . ?

_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_10735
_database_code_depnum_ccdc_archive 'CCDC 1835486'
loop_
_audit_author_name
_audit_author_address
Lirongyang
;Henan University
China
;
_audit_update_record             
;
2020-08-14 deposited with the CCDC.	2020-08-19 downloaded from the CCDC.
;
_audit_creation_date             2020-08-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H10 Nd O11, C9 H8 N2'
_chemical_formula_sum            'C25 H18 N2 Nd O11'
_chemical_formula_weight         666.65
_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'
Nd Nd -0.1943 3.0179 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.2535(18)
_cell_length_b                   8.5688(9)
_cell_length_c                   19.213(2)
_cell_angle_alpha                90
_cell_angle_beta                 114.7074(16)
_cell_angle_gamma                90
_cell_volume                     2430.9(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7174
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.45
_cell_measurement_theta_min      2.65
_shelx_estimated_absorpt_T_max   0.879
_shelx_estimated_absorpt_T_min   0.473
_exptl_absorpt_coefficient_mu    2.204
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5637
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0997 before and 0.0525 after correction. The Ratio of minimum to maximum transmission is 0.7559. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.822
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15058
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.445
_diffrn_reflns_theta_min         2.158
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker Smart APEX II CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5179
_reflns_number_total             5981
_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       'APEX 2'
_computing_data_collection       'APEX 2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.662
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         5981
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0257
_refine_ls_restrained_S_all      1.031
_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)+(0.0185P)²+0.8579P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0589
_refine_ls_wR_factor_ref         0.0621
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All O(H,H) groups
2.a Riding coordinates:
 O1W(H1WA,H1WB), O2W(H2WA,H2WB)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C12(H12), C14(H14),
 C15(H15), C20(H20), C21(H21), C22(H22), N1(H1A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Nd1 Nd 0.63377(2) 0.58829(2) 0.03666(2) 0.01467(5) Uani 1 1 d . . . . .
C1 C 0.07645(19) 0.9947(4) 0.32579(16) 0.0344(7) Uani 1 1 d . . . . .
H1 H 0.130287 1.039334 0.329481 0.041 Uiso 1 1 calc R . . . .
C2 C -0.03104(19) 0.9062(4) 0.35542(17) 0.0330(7) Uani 1 1 d . . . . .
H2 H -0.063334 0.880085 0.383891 0.040 Uiso 1 1 calc R . . . .
C3 C -0.05773(19) 0.8834(3) 0.27980(16) 0.0296(6) Uani 1 1 d . . . . .
H3 H -0.111794 0.838173 0.246170 0.036 Uiso 1 1 calc R . . . .
C4 C 0.0072(2) 0.9531(4) 0.18575(16) 0.0338(7) Uani 1 1 d . . . . .
C5 C -0.0659(2) 1.0233(5) 0.12876(17) 0.0486(9) Uani 1 1 d . . . . .
H5 H -0.113998 1.058567 0.138696 0.058 Uiso 1 1 calc R . . . .
C6 C -0.0678(2) 1.0414(5) 0.05668(17) 0.0461(9) Uani 1 1 d . . . . .
H6 H -0.117451 1.090129 0.018700 0.055 Uiso 1 1 calc R . . . .
C7 C 0.0014(2) 0.9896(4) 0.03957(16) 0.0407(8) Uani 1 1 d . . . . .
C8 C 0.0752(3) 0.9230(6) 0.0982(2) 0.0843(18) Uani 1 1 d . . . . .
H8 H 0.124036 0.889988 0.088736 0.101 Uiso 1 1 calc R . . . .
C9 C 0.0782(3) 0.9040(6) 0.1715(2) 0.0758(16) Uani 1 1 d . . . . .
H9 H 0.128358 0.858105 0.210180 0.091 Uiso 1 1 calc R . . . .
C10 C 0.30345(16) 0.7640(3) -0.10069(14) 0.0205(5) Uani 1 1 d . . . . .
C11 C 0.33232(16) 0.8323(3) -0.15949(13) 0.0168(5) Uani 1 1 d . . . . .
C12 C 0.27234(17) 0.9326(3) -0.21397(14) 0.0196(5) Uani 1 1 d . . . . .
H12 H 0.214229 0.946453 -0.216893 0.024 Uiso 1 1 calc R . . . .
C13 C 0.29903(16) 1.0120(3) -0.26394(12) 0.0174(5) Uani 1 1 d . . . . .
C14 C 0.38410(17) 0.9900(3) -0.26202(14) 0.0228(5) Uani 1 1 d . . . . .
H14 H 0.401380 1.043286 -0.295933 0.027 Uiso 1 1 calc R . . . .
C15 C 0.44329(18) 0.8877(3) -0.20902(15) 0.0228(5) Uani 1 1 d . . . . .
H15 H 0.500471 0.871538 -0.207766 0.027 Uiso 1 1 calc R . . . .
C16 C 0.41811(16) 0.8076(3) -0.15691(13) 0.0176(5) Uani 1 1 d . . . . .
C17 C 0.48678(16) 0.7039(3) -0.09904(13) 0.0165(5) Uani 1 1 d . . . . .
C18 C 0.67152(17) 0.6634(3) 0.19355(13) 0.0213(5) Uani 1 1 d . . . . .
C19 C 0.69050(17) 0.6414(3) 0.27644(13) 0.0200(5) Uani 1 1 d . . . . .
C20 C 0.6643(2) 0.5005(3) 0.29667(16) 0.0301(6) Uani 1 1 d . . . . .
H20 H 0.634162 0.427144 0.258863 0.036 Uiso 1 1 calc R . . . .
C21 C 0.6821(2) 0.4676(3) 0.37177(17) 0.0335(7) Uani 1 1 d . . . . .
H21 H 0.665757 0.371641 0.384776 0.040 Uiso 1 1 calc R . . . .
C22 C 0.72445(19) 0.5779(3) 0.42749(15) 0.0251(6) Uani 1 1 d . . . . .
H22 H 0.734588 0.556977 0.477923 0.030 Uiso 1 1 calc R . . . .
C23 C 0.75236(16) 0.7204(3) 0.40965(13) 0.0181(5) Uani 1 1 d . . . . .
C24 C 0.79898(17) 0.8344(3) 0.47377(13) 0.0219(5) Uani 1 1 d . . . . .
C25 C 0.73551(15) 0.7502(3) 0.33351(12) 0.0158(5) Uani 1 1 d . . . . .
N1 N 0.05260(16) 0.9751(3) 0.38263(13) 0.0337(6) Uani 1 1 d . . . . .
H1A H 0.084431 1.001441 0.429492 0.040 Uiso 1 1 calc R . . . .
N2 N 0.01027(16) 0.9397(3) 0.26171(13) 0.0305(5) Uani 1 1 d . . . . .
O1 O 0.59093(12) 0.6383(2) 0.14437(10) 0.0285(4) Uani 1 1 d . . . . .
O2 O 0.73439(12) 0.6936(2) 0.17364(10) 0.0272(4) Uani 1 1 d . . . . .
O3 O 0.76531(11) 0.89017(19) 0.31563(9) 0.0192(4) Uani 1 1 d . . . . .
O4 O 0.86622(14) 0.9068(3) 0.47719(11) 0.0401(6) Uani 1 1 d . . . . .
O5 O 0.76677(12) 0.8457(2) 0.52363(10) 0.0273(4) Uani 1 1 d . . . . .
O6 O 0.56305(12) 0.6896(2) -0.09822(10) 0.0253(4) Uani 1 1 d . . . . .
O7 O 0.46707(11) 0.6352(2) -0.04808(9) 0.0192(4) Uani 1 1 d . . . . .
O8 O 0.30836(15) 0.8513(2) -0.04724(11) 0.0346(5) Uani 1 1 d . . . . .
O9 O 0.27498(12) 0.6253(2) -0.10978(10) 0.0236(4) Uani 1 1 d . . . . .
O1W O 0.61274(15) 0.3782(2) -0.06202(11) 0.0350(5) Uani 1 1 d . . . . .
H1WA H 0.558558 0.357376 -0.092883 0.042 Uiso 1 1 d R . . . .
H1WB H 0.640208 0.292106 -0.046093 0.042 Uiso 1 1 d R . . . .
O2W O 0.59828(16) 0.8796(2) 0.03830(12) 0.0362(5) Uani 1 1 d . . . . .
H2WA H 0.576885 0.891564 0.071460 0.043 Uiso 1 1 d R . . . .
H2WB H 0.624345 0.964174 0.036030 0.043 Uiso 1 1 d R . . . .


_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
Nd1 O1 2.4809(18) . ?
Nd1 O2 2.6109(17) . ?
Nd1 O5 2.3469(18) 4_575 ?
Nd1 O6 2.5099(17) . ?
Nd1 O7 2.5427(16) . ?
Nd1 O7 2.5888(17) 3_665 ?
Nd1 O9 2.4041(17) 3_665 ?
Nd1 O1W 2.5321(19) . ?
Nd1 O2W 2.5648(19) . ?
C1 H1 0.9300 . ?
C1 N1 1.313(4) . ?
C1 N2 1.337(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.346(4) . ?
C2 N1 1.370(4) . ?
C3 H3 0.9300 . ?
C3 N2 1.377(4) . ?
C4 C5 1.373(4) . ?
C4 C9 1.359(5) . ?
C4 N2 1.444(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.381(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.371(5) . ?
C7 C7 1.513(6) 3_575 ?
C7 C8 1.380(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.398(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.511(3) . ?
C10 O8 1.246(3) . ?
C10 O9 1.261(3) . ?
C11 C12 1.390(3) . ?
C11 C16 1.391(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.386(3) . ?
C13 C14 1.381(3) . ?
C13 O3 1.384(3) 3_675 ?
C14 H14 0.9300 . ?
C14 C15 1.383(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.408(3) . ?
C16 C17 1.494(3) . ?
C17 O6 1.239(3) . ?
C17 O7 1.293(3) . ?
C18 C19 1.502(3) . ?
C18 O1 1.273(3) . ?
C18 O2 1.259(3) . ?
C19 C20 1.389(4) . ?
C19 C25 1.391(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.377(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.377(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.394(3) . ?
C23 C24 1.505(3) . ?
C23 C25 1.395(3) . ?
C24 O4 1.234(3) . ?
C24 O5 1.273(3) . ?
C25 O3 1.390(3) . ?
N1 H1A 0.8600 . ?
O1W H1WA 0.8499 . ?
O1W H1WB 0.8501 . ?
O2W H2WA 0.8500 . ?
O2W H2WB 0.8500 . ?

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 Nd1 O2 51.35(6) . . ?
O1 Nd1 O6 129.38(6) . . ?
O1 Nd1 O7 69.43(6) . 3_665 ?
O1 Nd1 O7 84.91(6) . . ?
O1 Nd1 O1W 138.60(7) . . ?
O1 Nd1 O2W 71.26(7) . . ?
O5 Nd1 O1 129.75(6) 4_575 . ?
O5 Nd1 O2 78.90(6) 4_575 . ?
O5 Nd1 O6 81.45(6) 4_575 . ?
O5 Nd1 O7 132.54(6) 4_575 . ?
O5 Nd1 O7 146.24(6) 4_575 3_665 ?
O5 Nd1 O9 82.83(6) 4_575 3_665 ?
O5 Nd1 O1W 86.20(7) 4_575 . ?
O5 Nd1 O2W 89.35(7) 4_575 . ?
O6 Nd1 O2 138.15(6) . . ?
O6 Nd1 O7 51.59(5) . . ?
O6 Nd1 O7 108.07(5) . 3_665 ?
O6 Nd1 O1W 67.20(6) . . ?
O6 Nd1 O2W 70.61(6) . . ?
O7 Nd1 O2 129.91(6) . . ?
O7 Nd1 O2 108.79(5) 3_665 . ?
O7 Nd1 O7 68.17(6) . 3_665 ?
O7 Nd1 O2W 70.68(6) . . ?
O9 Nd1 O1 87.92(7) 3_665 . ?
O9 Nd1 O2 72.57(6) 3_665 . ?
O9 Nd1 O6 140.44(6) 3_665 . ?
O9 Nd1 O7 69.22(6) 3_665 3_665 ?
O9 Nd1 O7 136.58(6) 3_665 . ?
O9 Nd1 O1W 75.73(6) 3_665 . ?
O9 Nd1 O2W 145.13(6) 3_665 . ?
O1W Nd1 O2 146.32(6) . . ?
O1W Nd1 O7 81.87(6) . . ?
O1W Nd1 O7 69.23(6) . 3_665 ?
O1W Nd1 O2W 137.77(6) . . ?
O2W Nd1 O2 72.58(6) . . ?
O2W Nd1 O7 124.41(6) . 3_665 ?
N1 C1 H1 125.8 . . ?
N1 C1 N2 108.5(3) . . ?
N2 C1 H1 125.8 . . ?
C3 C2 H2 126.4 . . ?
C3 C2 N1 107.2(3) . . ?
N1 C2 H2 126.4 . . ?
C2 C3 H3 126.5 . . ?
C2 C3 N2 106.9(2) . . ?
N2 C3 H3 126.5 . . ?
C5 C4 N2 119.6(3) . . ?
C9 C4 C5 120.0(3) . . ?
C9 C4 N2 120.4(3) . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 119.9(3) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 H6 119.1 . . ?
C7 C6 C5 121.8(3) . . ?
C7 C6 H6 119.1 . . ?
C6 C7 C7 121.4(4) . 3_575 ?
C6 C7 C8 117.3(3) . . ?
C8 C7 C7 121.3(4) . 3_575 ?
C7 C8 H8 119.2 . . ?
C7 C8 C9 121.6(4) . . ?
C9 C8 H8 119.2 . . ?
C4 C9 C8 119.4(3) . . ?
C4 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
O8 C10 C11 116.8(2) . . ?
O8 C10 O9 125.0(2) . . ?
O9 C10 C11 118.2(2) . . ?
C12 C11 C10 117.6(2) . . ?
C12 C11 C16 119.9(2) . . ?
C16 C11 C10 122.3(2) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.1(2) . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 121.0(2) . . ?
C14 C13 O3 123.4(2) . 3_675 ?
O3 C13 C12 115.7(2) 3_675 . ?
C13 C14 H14 120.4 . . ?
C13 C14 C15 119.1(2) . . ?
C15 C14 H14 120.4 . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.9(2) . . ?
C16 C15 H15 119.6 . . ?
C11 C16 C15 119.0(2) . . ?
C11 C16 C17 122.9(2) . . ?
C15 C16 C17 118.0(2) . . ?
O6 C17 C16 120.0(2) . . ?
O6 C17 O7 120.6(2) . . ?
O7 C17 C16 119.3(2) . . ?
O1 C18 C19 117.2(2) . . ?
O2 C18 C19 121.0(2) . . ?
O2 C18 O1 121.6(2) . . ?
C20 C19 C18 117.0(2) . . ?
C20 C19 C25 118.9(2) . . ?
C25 C19 C18 124.0(2) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 121.1(3) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 H21 120.3 . . ?
C20 C21 C22 119.5(3) . . ?
C22 C21 H21 120.3 . . ?
C21 C22 H22 119.4 . . ?
C21 C22 C23 121.2(2) . . ?
C23 C22 H22 119.4 . . ?
C22 C23 C24 118.1(2) . . ?
C22 C23 C25 118.4(2) . . ?
C25 C23 C24 123.4(2) . . ?
O4 C24 C23 120.1(2) . . ?
O4 C24 O5 123.8(2) . . ?
O5 C24 C23 116.1(2) . . ?
C19 C25 C23 120.8(2) . . ?
O3 C25 C19 120.4(2) . . ?
O3 C25 C23 118.8(2) . . ?
C1 N1 C2 109.2(2) . . ?
C1 N1 H1A 125.4 . . ?
C2 N1 H1A 125.4 . . ?
C1 N2 C3 108.2(2) . . ?
C1 N2 C4 125.2(3) . . ?
C3 N2 C4 126.2(2) . . ?
C18 O1 Nd1 95.04(15) . . ?
C18 O2 Nd1 89.38(14) . . ?
C13 O3 C25 117.62(18) 3_675 . ?
C24 O5 Nd1 141.76(16) . 4_576 ?
C17 O6 Nd1 94.10(14) . . ?
Nd1 O7 Nd1 111.84(6) . 3_665 ?
C17 O7 Nd1 140.14(15) . 3_665 ?
C17 O7 Nd1 91.25(13) . . ?
C10 O9 Nd1 122.39(15) . 3_665 ?
Nd1 O1W H1WA 116.6 . . ?
Nd1 O1W H1WB 117.5 . . ?
H1WA O1W H1WB 107.7 . . ?
Nd1 O2W H2WA 106.9 . . ?
Nd1 O2W H2WB 135.2 . . ?
H2WA O2W H2WB 107.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1 O2 0.93 2.59 3.511(4) 171.8 2_655 yes
C1 H1 O9 0.93 2.57 3.108(3) 117.6 4_576 yes
C2 H2 O3 0.93 2.54 3.073(3) 117.1 1_455 yes
C2 H2 O4 0.93 2.51 3.395(4) 159.5 1_455 yes
C3 H3 O2 0.93 2.61 3.530(3) 169.9 1_455 yes
C14 H14 O6 0.93 2.65 3.578(3) 175.2 2_654 yes
O1W H1WA O1 0.85 2.21 3.017(3) 159.1 3_665 yes
O1W H1WB O8 0.85 2.04 2.769(3) 143.0 3_665 yes
O2W H2WB O8 0.85 1.88 2.726(3) 171.3 3_675 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C3 N2 C1 0.2(3) . . . . ?
C2 C3 N2 C4 -173.7(3) . . . . ?
C3 C2 N1 C1 0.3(4) . . . . ?
C4 C5 C6 C7 0.7(6) . . . . ?
C5 C4 C9 C8 -1.2(7) . . . . ?
C5 C4 N2 C1 -123.3(4) . . . . ?
C5 C4 N2 C3 49.5(5) . . . . ?
C5 C6 C7 C7 -179.9(4) . . . 3_575 ?
C5 C6 C7 C8 -2.2(6) . . . . ?
C6 C7 C8 C9 2.1(7) . . . . ?
C7 C7 C8 C9 179.8(5) 3_575 . . . ?
C7 C8 C9 C4 -0.5(8) . . . . ?
C9 C4 C5 C6 1.1(6) . . . . ?
C9 C4 N2 C1 53.4(5) . . . . ?
C9 C4 N2 C3 -133.8(4) . . . . ?
C10 C11 C12 C13 172.9(2) . . . . ?
C10 C11 C16 C15 -173.6(2) . . . . ?
C10 C11 C16 C17 3.9(4) . . . . ?
C11 C10 O9 Nd1 103.2(2) . . . 3_665 ?
C11 C12 C13 C14 1.8(4) . . . . ?
C11 C12 C13 O3 -179.5(2) . . . 3_675 ?
C11 C16 C17 O6 -178.1(2) . . . . ?
C11 C16 C17 O7 -1.0(3) . . . . ?
C12 C11 C16 C15 1.2(4) . . . . ?
C12 C11 C16 C17 178.8(2) . . . . ?
C12 C13 C14 C15 -0.3(4) . . . . ?
C13 C14 C15 C16 -0.6(4) . . . . ?
C14 C15 C16 C11 0.2(4) . . . . ?
C14 C15 C16 C17 -177.5(2) . . . . ?
C15 C16 C17 O6 -0.5(3) . . . . ?
C15 C16 C17 O7 176.5(2) . . . . ?
C16 C11 C12 C13 -2.2(4) . . . . ?
C16 C17 O6 Nd1 160.74(18) . . . . ?
C16 C17 O7 Nd1 -161.01(18) . . . . ?
C16 C17 O7 Nd1 71.6(3) . . . 3_665 ?
C18 C19 C20 C21 177.4(3) . . . . ?
C18 C19 C25 C23 -178.7(2) . . . . ?
C18 C19 C25 O3 0.7(4) . . . . ?
C19 C18 O1 Nd1 -157.38(19) . . . . ?
C19 C18 O2 Nd1 158.1(2) . . . . ?
C19 C20 C21 C22 1.8(5) . . . . ?
C19 C25 O3 C13 59.7(3) . . . 3_675 ?
C20 C19 C25 C23 -1.5(4) . . . . ?
C20 C19 C25 O3 177.9(2) . . . . ?
C20 C21 C22 C23 -2.2(4) . . . . ?
C21 C22 C23 C24 -179.4(3) . . . . ?
C21 C22 C23 C25 0.8(4) . . . . ?
C22 C23 C24 O4 137.5(3) . . . . ?
C22 C23 C24 O5 -40.2(3) . . . . ?
C22 C23 C25 C19 1.1(4) . . . . ?
C22 C23 C25 O3 -178.3(2) . . . . ?
C23 C24 O5 Nd1 -60.6(4) . . . 4_576 ?
C23 C25 O3 C13 -120.9(2) . . . 3_675 ?
C24 C23 C25 C19 -178.7(2) . . . . ?
C24 C23 C25 O3 1.9(3) . . . . ?
C25 C19 C20 C21 0.0(4) . . . . ?
C25 C23 C24 O4 -42.7(4) . . . . ?
C25 C23 C24 O5 139.6(2) . . . . ?
N1 C1 N2 C3 0.0(4) . . . . ?
N1 C1 N2 C4 173.9(3) . . . . ?
N1 C2 C3 N2 -0.3(3) . . . . ?
N2 C1 N1 C2 -0.2(4) . . . . ?
N2 C4 C5 C6 177.8(3) . . . . ?
N2 C4 C9 C8 -177.8(4) . . . . ?
O1 C18 C19 C20 52.0(3) . . . . ?
O1 C18 C19 C25 -130.8(3) . . . . ?
O1 C18 O2 Nd1 -16.3(3) . . . . ?
O2 C18 C19 C20 -122.7(3) . . . . ?
O2 C18 C19 C25 54.5(4) . . . . ?
O2 C18 O1 Nd1 17.3(3) . . . . ?
O3 C13 C14 C15 -178.9(2) 3_675 . . . ?
O4 C24 O5 Nd1 121.8(3) . . . 4_576 ?
O6 C17 O7 Nd1 -111.3(2) . . . 3_665 ?
O6 C17 O7 Nd1 16.0(2) . . . . ?
O7 C17 O6 Nd1 -16.3(2) . . . . ?
O8 C10 C11 C12 -77.1(3) . . . . ?
O8 C10 C11 C16 97.9(3) . . . . ?
O8 C10 O9 Nd1 -78.1(3) . . . 3_665 ?
O9 C10 C11 C12 101.7(3) . . . . ?
O9 C10 C11 C16 -83.3(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_10723
_database_code_depnum_ccdc_archive 'CCDC 1835485'
loop_
_audit_author_name
_audit_author_address
Lirongyang
;Henan University
China
;
_audit_update_record             
;
2020-08-14 deposited with the CCDC.	2020-08-19 downloaded from the CCDC.
;
_audit_creation_date             2020-08-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H10 Ce O11, C9 H8 N2'
_chemical_formula_sum            'C25 H18 Ce N2 O11'
_chemical_formula_weight         662.53
_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'
Ce Ce -0.2486 2.6331 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.2883(10)
_cell_length_b                   8.5827(5)
_cell_length_c                   19.2359(12)
_cell_angle_alpha                90
_cell_angle_beta                 114.7250(9)
_cell_angle_gamma                90
_cell_volume                     2442.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5800
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.33
_shelx_estimated_absorpt_T_max   0.877
_shelx_estimated_absorpt_T_min   0.512
_exptl_absorpt_coefficient_mu    1.932
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6250
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0838 before and 0.0440 after correction. The Ratio of minimum to maximum transmission is 0.8381. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.802
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            15164
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.326
_diffrn_reflns_theta_min         2.155
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker Smart APEX II CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4941
_reflns_number_total             5972
_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       'APEX 2'
_computing_data_collection       'APEX 2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.622
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         5972
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0280
_refine_ls_restrained_S_all      1.012
_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)+(0.0204P)²+1.5007P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0592
_refine_ls_wR_factor_ref         0.0637
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All O(H,H) groups
2.a Riding coordinates:
 O1W(H1WA,H1WB), O2W(H2WA,H2WB)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C12(H12),
 C14(H14), C15(H15), C20(H20), C21(H21), C22(H22)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ce1 Ce 0.13445(2) 1.08935(2) 0.53701(2) 0.01577(5) Uani 1 1 d . . . . .
N1 N 0.44856(17) 0.9764(3) 0.61818(15) 0.0349(6) Uani 1 1 d . . . . .
H1 H 0.417062 1.003063 0.571390 0.042 Uiso 1 1 calc R . . . .
N2 N 0.49016(17) 0.9408(3) 0.73919(14) 0.0319(6) Uani 1 1 d . . . . .
O1 O 0.22678(13) 0.8740(2) 0.61166(11) 0.0253(4) Uani 1 1 d . . . . .
O2 O 0.19200(17) 0.6488(3) 0.54870(12) 0.0374(6) Uani 1 1 d . . . . .
O3 O 0.03400(12) 0.8648(2) 0.54965(10) 0.0205(4) Uani 1 1 d . . . . .
O4 O -0.06168(13) 0.8108(2) 0.60005(11) 0.0264(5) Uani 1 1 d . . . . .
O5 O 0.26557(12) 1.3912(2) 0.81663(10) 0.0208(4) Uani 1 1 d . . . . .
O6 O 0.23437(14) 1.1959(2) 0.67517(11) 0.0287(5) Uani 1 1 d . . . . .
O7 O 0.09103(14) 1.1419(3) 0.64566(11) 0.0310(5) Uani 1 1 d . . . . .
O8 O 0.36840(15) 1.4051(3) 0.97794(12) 0.0412(6) Uani 1 1 d . . . . .
O9 O 0.26934(13) 1.3454(3) 1.02479(11) 0.0292(5) Uani 1 1 d . . . . .
O1W O 0.11268(17) 0.8745(3) 0.43735(13) 0.0388(6) Uani 1 1 d . . . . .
H1WA H 0.131296 0.793040 0.464644 0.047 Uiso 1 1 d R . . . .
H1WB H 0.055466 0.865320 0.416744 0.047 Uiso 1 1 d R . . . .
O2W O 0.09616(17) 1.3837(2) 0.53692(13) 0.0393(6) Uani 1 1 d . . . . .
H2WA H 0.079404 1.477448 0.524863 0.047 Uiso 1 1 d R . . . .
H2WB H 0.103904 1.375938 0.583313 0.047 Uiso 1 1 d R . . . .
C1 C 0.4245(2) 0.9954(4) 0.67480(18) 0.0359(8) Uani 1 1 d . . . . .
H1A H 0.370609 1.039708 0.670796 0.043 Uiso 1 1 calc R . . . .
C2 C 0.5318(2) 0.9073(4) 0.64564(18) 0.0340(7) Uani 1 1 d . . . . .
H2 H 0.564144 0.881430 0.617308 0.041 Uiso 1 1 calc R . . . .
C3 C 0.5582(2) 0.8835(4) 0.72087(18) 0.0315(7) Uani 1 1 d . . . . .
H3 H 0.611925 0.837345 0.754310 0.038 Uiso 1 1 calc R . . . .
C4 C 0.4929(2) 0.9547(4) 0.81459(18) 0.0351(8) Uani 1 1 d . . . . .
C5 C 0.5654(2) 1.0236(5) 0.87147(19) 0.0488(10) Uani 1 1 d . . . . .
H5 H 0.613718 1.058019 0.861691 0.059 Uiso 1 1 calc R . . . .
C6 C 0.5675(2) 1.0425(5) 0.94376(19) 0.0464(10) Uani 1 1 d . . . . .
H6 H 0.616950 1.091680 0.981549 0.056 Uiso 1 1 calc R . . . .
C7 C 0.4985(2) 0.9905(5) 0.96098(18) 0.0410(9) Uani 1 1 d . . . . .
C8 C 0.4252(3) 0.9238(7) 0.9017(3) 0.086(2) Uani 1 1 d . . . . .
H8 H 0.376544 0.889806 0.910973 0.103 Uiso 1 1 calc R . . . .
C9 C 0.4218(3) 0.9058(6) 0.8287(2) 0.0760(17) Uani 1 1 d . . . . .
H9 H 0.371537 0.860878 0.789981 0.091 Uiso 1 1 calc R . . . .
C10 C 0.19756(18) 0.7362(3) 0.60221(16) 0.0219(6) Uani 1 1 d . . . . .
C11 C 0.16864(18) 0.6683(3) 0.66079(15) 0.0183(5) Uani 1 1 d . . . . .
C12 C 0.22802(19) 0.5677(3) 0.71497(15) 0.0208(6) Uani 1 1 d . . . . .
H12 H 0.285881 0.553301 0.717691 0.025 Uiso 1 1 calc R . . . .
C13 C 0.20168(18) 0.4887(3) 0.76503(14) 0.0188(5) Uani 1 1 d . . . . .
C14 C 0.11675(19) 0.5109(3) 0.76342(15) 0.0245(6) Uani 1 1 d . . . . .
H14 H 0.099511 0.458383 0.797471 0.029 Uiso 1 1 calc R . . . .
C15 C 0.0581(2) 0.6129(3) 0.71009(16) 0.0243(6) Uani 1 1 d . . . . .
H15 H 0.000934 0.628834 0.708647 0.029 Uiso 1 1 calc R . . . .
C16 C 0.08261(18) 0.6926(3) 0.65827(15) 0.0183(5) Uani 1 1 d . . . . .
C17 C 0.01495(18) 0.7963(3) 0.60045(14) 0.0182(5) Uani 1 1 d . . . . .
C18 C 0.1713(2) 1.1667(3) 0.69450(15) 0.0230(6) Uani 1 1 d . . . . .
C19 C 0.19070(19) 1.1440(3) 0.77745(15) 0.0212(6) Uani 1 1 d . . . . .
C20 C 0.1641(2) 1.0032(4) 0.79752(18) 0.0322(7) Uani 1 1 d . . . . .
H20 H 0.133412 0.930632 0.759603 0.039 Uiso 1 1 calc R . . . .
C21 C 0.1825(2) 0.9696(4) 0.87255(19) 0.0354(8) Uani 1 1 d . . . . .
H21 H 0.166138 0.873853 0.885592 0.043 Uiso 1 1 calc R . . . .
C22 C 0.2253(2) 1.0792(3) 0.92785(17) 0.0281(7) Uani 1 1 d . . . . .
H22 H 0.235719 1.058112 0.978267 0.034 Uiso 1 1 calc R . . . .
C23 C 0.25362(18) 1.2209(3) 0.91057(14) 0.0192(5) Uani 1 1 d . . . . .
C24 C 0.23607(17) 1.2512(3) 0.83455(14) 0.0177(5) Uani 1 1 d . . . . .
C25 C 0.30060(19) 1.3337(3) 0.97450(15) 0.0225(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ce1 O1 2.4358(19) . ?
Ce1 O3 2.5760(18) 3_576 ?
Ce1 O3 2.6043(18) . ?
Ce1 O4 2.5450(19) 3_576 ?
Ce1 O6 2.6322(19) . ?
Ce1 O7 2.512(2) . ?
Ce1 O9 2.3724(19) 4_585 ?
Ce1 O1W 2.575(2) . ?
Ce1 O2W 2.602(2) . ?
Ce1 C17 2.915(3) 3_576 ?
N1 H1 0.8600 . ?
N1 C1 1.312(4) . ?
N1 C2 1.367(4) . ?
N2 C1 1.338(4) . ?
N2 C3 1.386(4) . ?
N2 C4 1.437(4) . ?
O1 C10 1.259(3) . ?
O2 C10 1.246(3) . ?
O3 C17 1.285(3) . ?
O4 C17 1.251(3) . ?
O5 C13 1.380(3) 1_565 ?
O5 C24 1.390(3) . ?
O6 C18 1.255(3) . ?
O7 C18 1.269(3) . ?
O8 C25 1.240(3) . ?
O9 C25 1.272(3) . ?
O1W H1WA 0.8503 . ?
O1W H1WB 0.8501 . ?
O2W H2WA 0.8501 . ?
O2W H2WB 0.8500 . ?
C1 H1A 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.342(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(5) . ?
C4 C9 1.361(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.373(5) . ?
C7 C7 1.491(6) 3_677 ?
C7 C8 1.383(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.389(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.509(4) . ?
C11 C12 1.387(4) . ?
C11 C16 1.397(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.385(4) . ?
C13 C14 1.384(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.382(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.398(4) . ?
C16 C17 1.490(4) . ?
C18 C19 1.504(4) . ?
C19 C20 1.392(4) . ?
C19 C24 1.385(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.376(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.372(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.389(4) . ?
C23 C24 1.392(3) . ?
C23 C25 1.500(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Ce1 O3 136.48(6) . 3_576 ?
O1 Ce1 O3 68.93(6) . . ?
O1 Ce1 O4 140.48(7) . 3_576 ?
O1 Ce1 O6 72.53(7) . . ?
O1 Ce1 O7 87.99(7) . . ?
O1 Ce1 O1W 75.78(7) . . ?
O1 Ce1 O2W 145.68(7) . . ?
O1 Ce1 C17 149.96(7) . 3_576 ?
O3 Ce1 O3 68.45(7) 3_576 . ?
O3 Ce1 O6 108.06(6) . . ?
O3 Ce1 O6 129.92(6) 3_576 . ?
O3 Ce1 O2W 70.20(7) 3_576 . ?
O3 Ce1 C17 90.86(7) . 3_576 ?
O3 Ce1 C17 26.14(6) 3_576 3_576 ?
O4 Ce1 O3 50.92(6) 3_576 3_576 ?
O4 Ce1 O3 107.90(6) 3_576 . ?
O4 Ce1 O6 138.80(7) 3_576 . ?
O4 Ce1 O1W 67.08(7) 3_576 . ?
O4 Ce1 O2W 70.41(7) 3_576 . ?
O4 Ce1 C17 25.36(6) 3_576 3_576 ?
O6 Ce1 C17 136.73(7) . 3_576 ?
O7 Ce1 O3 69.42(6) . . ?
O7 Ce1 O3 85.22(6) . 3_576 ?
O7 Ce1 O4 129.08(7) . 3_576 ?
O7 Ce1 O6 50.80(6) . . ?
O7 Ce1 O1W 138.49(7) . . ?
O7 Ce1 O2W 71.06(7) . . ?
O7 Ce1 C17 106.00(7) . 3_576 ?
O9 Ce1 O1 82.45(7) 4_585 . ?
O9 Ce1 O3 132.82(6) 4_585 3_576 ?
O9 Ce1 O3 145.89(7) 4_585 . ?
O9 Ce1 O4 82.37(6) 4_585 3_576 ?
O9 Ce1 O6 79.11(6) 4_585 . ?
O9 Ce1 O7 129.42(7) 4_585 . ?
O9 Ce1 O1W 86.57(8) 4_585 . ?
O9 Ce1 O2W 90.14(8) 4_585 . ?
O9 Ce1 C17 106.68(7) 4_585 3_576 ?
O1W Ce1 O3 81.36(7) . 3_576 ?
O1W Ce1 O3 69.10(7) . . ?
O1W Ce1 O6 146.58(7) . . ?
O1W Ce1 O2W 137.42(7) . . ?
O1W Ce1 C17 76.29(7) . 3_576 ?
O2W Ce1 O3 123.97(7) . . ?
O2W Ce1 O6 73.16(7) . . ?
O2W Ce1 C17 64.12(7) . 3_576 ?
C1 N1 H1 125.5 . . ?
C1 N1 C2 109.0(3) . . ?
C2 N1 H1 125.5 . . ?
C1 N2 C3 107.7(3) . . ?
C1 N2 C4 125.5(3) . . ?
C3 N2 C4 126.5(3) . . ?
C10 O1 Ce1 121.64(17) . . ?
Ce1 O3 Ce1 111.55(7) 3_576 . ?
C17 O3 Ce1 140.41(17) . . ?
C17 O3 Ce1 91.80(15) . 3_576 ?
C17 O4 Ce1 94.07(15) . 3_576 ?
C13 O5 C24 117.9(2) 1_565 . ?
C18 O6 Ce1 89.59(16) . . ?
C18 O7 Ce1 94.85(16) . . ?
C25 O9 Ce1 140.90(18) . 4_586 ?
Ce1 O1W H1WA 103.1 . . ?
Ce1 O1W H1WB 101.3 . . ?
H1WA O1W H1WB 104.5 . . ?
Ce1 O2W H2WA 165.6 . . ?
Ce1 O2W H2WB 89.6 . . ?
H2WA O2W H2WB 104.5 . . ?
N1 C1 N2 108.9(3) . . ?
N1 C1 H1A 125.5 . . ?
N2 C1 H1A 125.5 . . ?
N1 C2 H2 126.2 . . ?
C3 C2 N1 107.6(3) . . ?
C3 C2 H2 126.2 . . ?
N2 C3 H3 126.6 . . ?
C2 C3 N2 106.8(3) . . ?
C2 C3 H3 126.6 . . ?
C5 C4 N2 119.7(3) . . ?
C9 C4 N2 120.4(3) . . ?
C9 C4 C5 119.8(3) . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.3(3) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.7(3) . . ?
C7 C6 H6 119.2 . . ?
C6 C7 C7 121.5(4) . 3_677 ?
C6 C7 C8 116.5(3) . . ?
C8 C7 C7 121.9(4) . 3_677 ?
C7 C8 H8 118.8 . . ?
C7 C8 C9 122.3(4) . . ?
C9 C8 H8 118.8 . . ?
C4 C9 C8 119.3(4) . . ?
C4 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
O1 C10 C11 118.2(2) . . ?
O2 C10 O1 125.3(3) . . ?
O2 C10 C11 116.5(2) . . ?
C12 C11 C10 117.7(2) . . ?
C12 C11 C16 119.5(2) . . ?
C16 C11 C10 122.6(2) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
O5 C13 C12 115.9(2) 1_545 . ?
O5 C13 C14 123.1(2) 1_545 . ?
C14 C13 C12 121.0(2) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 C13 118.5(3) . . ?
C15 C14 H14 120.7 . . ?
C14 C15 H15 119.2 . . ?
C14 C15 C16 121.6(3) . . ?
C16 C15 H15 119.2 . . ?
C11 C16 C15 118.9(2) . . ?
C11 C16 C17 122.2(2) . . ?
C15 C16 C17 118.8(2) . . ?
O3 C17 Ce1 62.06(13) . 3_576 ?
O3 C17 C16 120.2(2) . . ?
O4 C17 Ce1 60.57(14) . 3_576 ?
O4 C17 O3 120.5(2) . . ?
O4 C17 C16 119.2(2) . . ?
C16 C17 Ce1 162.72(18) . 3_576 ?
O6 C18 O7 122.1(2) . . ?
O6 C18 C19 120.3(3) . . ?
O7 C18 C19 117.3(2) . . ?
C20 C19 C18 117.1(2) . . ?
C24 C19 C18 124.1(2) . . ?
C24 C19 C20 118.8(2) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 121.1(3) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 H21 120.5 . . ?
C22 C21 C20 119.1(3) . . ?
C22 C21 H21 120.5 . . ?
C21 C22 H22 119.1 . . ?
C21 C22 C23 121.8(3) . . ?
C23 C22 H22 119.1 . . ?
C22 C23 C24 118.2(3) . . ?
C22 C23 C25 118.4(2) . . ?
C24 C23 C25 123.4(2) . . ?
O5 C24 C23 118.8(2) . . ?
C19 C24 O5 120.2(2) . . ?
C19 C24 C23 121.1(2) . . ?
O8 C25 O9 123.5(3) . . ?
O8 C25 C23 120.0(2) . . ?
O9 C25 C23 116.4(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1W H1WA O2 0.85 1.95 2.774(3) 164.2 . yes
O1W H1WB O7 0.85 2.18 3.024(3) 173.9 3_576 yes
O2W H2WA O2 0.85 2.24 2.714(3) 115.0 1_565 yes
O2W H2WB O6 0.85 2.62 3.119(3) 118.4 . yes
O2W H2WB O7 0.85 2.39 2.973(3) 125.9 . yes
C1 H1A O1 0.93 2.56 3.108(4) 117.8 . yes
C1 H1A O6 0.93 2.62 3.546(4) 171.1 . yes
C2 H2 O5 0.93 2.52 3.072(4) 118.1 2_646 yes
C2 H2 O8 0.93 2.51 3.396(4) 159.7 2_646 yes
C3 H3 O6 0.93 2.60 3.515(4) 169.4 2_646 yes
C14 H14 O4 0.93 2.62 3.553(3) 176.3 2_546 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ce1 O1 C10 O2 77.8(3) . . . . ?
Ce1 O1 C10 C11 -103.7(2) . . . . ?
Ce1 O3 C17 Ce1 127.9(2) . . . 3_576 ?
Ce1 O3 C17 O4 111.2(3) . . . . ?
Ce1 O3 C17 O4 -16.7(3) 3_576 . . . ?
Ce1 O3 C17 C16 160.4(2) 3_576 . . . ?
Ce1 O3 C17 C16 -71.7(3) . . . . ?
Ce1 O4 C17 O3 16.9(3) 3_576 . . . ?
Ce1 O4 C17 C16 -160.2(2) 3_576 . . . ?
Ce1 O6 C18 O7 -16.4(3) . . . . ?
Ce1 O6 C18 C19 157.4(2) . . . . ?
Ce1 O7 C18 O6 17.3(3) . . . . ?
Ce1 O7 C18 C19 -156.7(2) . . . . ?
Ce1 O9 C25 O8 123.6(3) 4_586 . . . ?
Ce1 O9 C25 C23 -59.4(4) 4_586 . . . ?
N1 C2 C3 N2 -0.6(4) . . . . ?
N2 C4 C5 C6 177.8(4) . . . . ?
N2 C4 C9 C8 -178.5(4) . . . . ?
O1 C10 C11 C12 -101.3(3) . . . . ?
O1 C10 C11 C16 84.1(3) . . . . ?
O2 C10 C11 C12 77.3(3) . . . . ?
O2 C10 C11 C16 -97.3(3) . . . . ?
O5 C13 C14 C15 179.1(3) 1_545 . . . ?
O6 C18 C19 C20 -122.6(3) . . . . ?
O6 C18 C19 C24 54.8(4) . . . . ?
O7 C18 C19 C20 51.5(4) . . . . ?
O7 C18 C19 C24 -131.2(3) . . . . ?
C1 N1 C2 C3 0.3(4) . . . . ?
C1 N2 C3 C2 0.7(4) . . . . ?
C1 N2 C4 C5 -123.6(4) . . . . ?
C1 N2 C4 C9 53.5(5) . . . . ?
C2 N1 C1 N2 0.2(4) . . . . ?
C3 N2 C1 N1 -0.6(4) . . . . ?
C3 N2 C4 C5 49.4(5) . . . . ?
C3 N2 C4 C9 -133.5(4) . . . . ?
C4 N2 C1 N1 173.5(3) . . . . ?
C4 N2 C3 C2 -173.3(3) . . . . ?
C4 C5 C6 C7 1.3(6) . . . . ?
C5 C4 C9 C8 -1.5(7) . . . . ?
C5 C6 C7 C7 179.3(5) . . . 3_677 ?
C5 C6 C7 C8 -2.5(7) . . . . ?
C6 C7 C8 C9 1.7(8) . . . . ?
C7 C7 C8 C9 179.9(5) 3_677 . . . ?
C7 C8 C9 C4 0.2(9) . . . . ?
C9 C4 C5 C6 0.7(6) . . . . ?
C10 C11 C12 C13 -173.1(2) . . . . ?
C10 C11 C16 C15 173.6(3) . . . . ?
C10 C11 C16 C17 -4.2(4) . . . . ?
C11 C12 C13 O5 179.8(2) . . . 1_545 ?
C11 C12 C13 C14 -1.6(4) . . . . ?
C11 C16 C17 Ce1 94.0(6) . . . 3_576 ?
C11 C16 C17 O3 1.4(4) . . . . ?
C11 C16 C17 O4 178.5(3) . . . . ?
C12 C11 C16 C15 -0.8(4) . . . . ?
C12 C11 C16 C17 -178.7(2) . . . . ?
C12 C13 C14 C15 0.6(4) . . . . ?
C13 O5 C24 C19 59.0(3) 1_565 . . . ?
C13 O5 C24 C23 -121.5(3) 1_565 . . . ?
C13 C14 C15 C16 0.2(4) . . . . ?
C14 C15 C16 C11 -0.1(4) . . . . ?
C14 C15 C16 C17 177.8(3) . . . . ?
C15 C16 C17 Ce1 -83.9(7) . . . 3_576 ?
C15 C16 C17 O3 -176.5(2) . . . . ?
C15 C16 C17 O4 0.6(4) . . . . ?
C16 C11 C12 C13 1.7(4) . . . . ?
C18 C19 C20 C21 177.2(3) . . . . ?
C18 C19 C24 O5 1.1(4) . . . . ?
C18 C19 C24 C23 -178.4(3) . . . . ?
C19 C20 C21 C22 2.0(5) . . . . ?
C20 C19 C24 O5 178.3(2) . . . . ?
C20 C19 C24 C23 -1.1(4) . . . . ?
C20 C21 C22 C23 -2.4(5) . . . . ?
C21 C22 C23 C24 1.1(4) . . . . ?
C21 C22 C23 C25 -179.5(3) . . . . ?
C22 C23 C24 O5 -178.7(2) . . . . ?
C22 C23 C24 C19 0.8(4) . . . . ?
C22 C23 C25 O8 137.2(3) . . . . ?
C22 C23 C25 O9 -40.0(4) . . . . ?
C24 C19 C20 C21 -0.2(5) . . . . ?
C24 C23 C25 O8 -43.5(4) . . . . ?
C24 C23 C25 O9 139.4(3) . . . . ?
C25 C23 C24 O5 1.9(4) . . . . ?
C25 C23 C24 C19 -178.6(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_10682
_database_code_depnum_ccdc_archive 'CCDC 1818344'
loop_
_audit_author_name
_audit_author_address
Lirongyang
;Henan University
China
;
_audit_update_record             
;
2020-08-14 deposited with the CCDC.	2020-08-19 downloaded from the CCDC.
;
_audit_creation_date             2020-08-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H10 O11 Sm, C9 H8 N2'
_chemical_formula_sum            'C25 H18 N2 O11 Sm'
_chemical_formula_weight         672.76
_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'
Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.2397(14)
_cell_length_b                   8.5555(7)
_cell_length_c                   19.2033(17)
_cell_angle_alpha                90
_cell_angle_beta                 114.7534(12)
_cell_angle_gamma                90
_cell_volume                     2422.9(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8561
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.16
_shelx_estimated_absorpt_T_max   0.865
_shelx_estimated_absorpt_T_min   0.407
_exptl_absorpt_coefficient_mu    2.492
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1412 before and 0.0607 after correction. The Ratio of minimum to maximum transmission is 0.6383. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.844
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14632
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.252
_diffrn_reflns_theta_min         1.381
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker Smart APEX II CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5147
_reflns_number_total             5862
_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       'APEX 2'
_computing_data_collection       'APEX 2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.282
_refine_diff_density_min         -1.310
_refine_diff_density_rms         0.156
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         5862
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0323
_refine_ls_restrained_S_all      1.072
_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)+(0.0517P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0931
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All O(H,H) groups
2.a Riding coordinates:
 O1W(H1WA,H1WB), O2W(H2WA,H2WB)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C12(H12),
 C13(H13), C14(H14), C20(H20), C21(H21), C23(H23)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sm1 Sm 0.13339(2) 0.58780(2) 1.03632(2) 0.01423(7) Uani 1 1 d . . . . .
N1 N 0.4893(2) 0.4382(4) 0.23792(17) 0.0298(7) Uani 1 1 d . . . . .
N2 N 0.4465(2) 0.4741(4) 0.11685(16) 0.0324(7) Uani 1 1 d . . . . .
H2 H 0.414396 0.499895 0.069909 0.039 Uiso 1 1 calc R . . . .
O1 O 0.09158(16) 0.6340(3) 1.14329(12) 0.0272(5) Uani 1 1 d . . . . .
O2 O 0.23503(16) 0.6916(3) 1.17310(13) 0.0268(5) Uani 1 1 d . . . . .
O3 O 0.26484(15) 0.6104(2) 0.81487(12) 0.0193(5) Uani 1 1 d . . . . .
O4 O 0.36440(19) 0.5922(3) 0.97631(16) 0.0387(8) Uani 1 1 d . . . . .
O5 O 0.26438(16) 0.6528(3) 1.02281(12) 0.0260(5) Uani 1 1 d . . . . .
O6 O -0.03188(15) 0.6359(3) 0.95353(11) 0.0199(4) Uani 1 1 d . . . . .
O7 O 0.06413(15) 0.6912(3) 0.90327(13) 0.0255(5) Uani 1 1 d . . . . .
O8 O 0.22392(15) 0.3770(3) 1.10866(13) 0.0226(5) Uani 1 1 d . . . . .
O9 O 0.1928(2) 0.1486(3) 1.04703(14) 0.0354(6) Uani 1 1 d . . . . .
O1W O 0.1001(2) 0.8764(3) 1.03929(15) 0.0361(6) Uani 1 1 d . . . . .
H1WA H 0.061090 0.902655 1.055932 0.043 Uiso 1 1 d R . . . .
H1WB H 0.121090 0.959595 1.028762 0.043 Uiso 1 1 d R . . . .
O2W O 0.1135(2) 0.3797(3) 0.93842(15) 0.0336(6) Uani 1 1 d . . . . .
H2WA H 0.062986 0.332059 0.928155 0.040 Uiso 1 1 d R . . . .
H2WB H 0.107386 0.427479 0.897614 0.040 Uiso 1 1 d R . . . .
C1 C 0.4925(3) 0.4535(5) 0.3136(2) 0.0338(8) Uani 1 1 d . . . . .
C2 C 0.4210(4) 0.4046(7) 0.3278(3) 0.074(2) Uani 1 1 d . . . . .
H2A H 0.370641 0.358766 0.289178 0.089 Uiso 1 1 calc R . . . .
C3 C 0.4246(4) 0.4243(8) 0.4015(3) 0.083(2) Uani 1 1 d . . . . .
H3 H 0.375405 0.392229 0.410873 0.100 Uiso 1 1 calc R . . . .
C4 C 0.4981(3) 0.4893(6) 0.4603(2) 0.0406(10) Uani 1 1 d . . . . .
C5 C 0.5684(3) 0.5405(6) 0.4435(2) 0.0454(10) Uani 1 1 d . . . . .
H5 H 0.618308 0.588570 0.481576 0.055 Uiso 1 1 calc R . . . .
C6 C 0.5662(3) 0.5218(6) 0.3712(2) 0.0462(11) Uani 1 1 d . . . . .
H6 H 0.614782 0.555547 0.361488 0.055 Uiso 1 1 calc R . . . .
C7 C 0.5575(3) 0.3822(4) 0.2197(2) 0.0293(8) Uani 1 1 d . . . . .
H7 H 0.611664 0.336643 0.253202 0.035 Uiso 1 1 calc R . . . .
C8 C 0.5303(3) 0.4064(4) 0.1435(2) 0.0316(8) Uani 1 1 d . . . . .
H8 H 0.562547 0.381517 0.114801 0.038 Uiso 1 1 calc R . . . .
C9 C 0.4224(2) 0.4940(5) 0.1735(2) 0.0333(8) Uani 1 1 d . . . . .
H9 H 0.368501 0.538858 0.169726 0.040 Uiso 1 1 calc R . . . .
C10 C 0.1715(2) 0.6604(4) 1.19260(17) 0.0207(6) Uani 1 1 d . . . . .
C11 C 0.1906(2) 0.8599(4) 0.77548(16) 0.0189(6) Uani 1 1 d . . . . .
C12 C 0.1641(3) 1.0022(4) 0.7959(2) 0.0291(8) Uani 1 1 d . . . . .
H12 H 0.134398 1.076177 0.758191 0.035 Uiso 1 1 calc R . . . .
C13 C 0.1815(3) 1.0338(4) 0.8712(2) 0.0323(8) Uani 1 1 d . . . . .
H13 H 0.164711 1.129408 0.884398 0.039 Uiso 1 1 calc R . . . .
C14 C 0.2239(3) 0.9226(4) 0.9270(2) 0.0239(7) Uani 1 1 d . . . . .
H14 H 0.234362 0.943444 0.977595 0.029 Uiso 1 1 calc R . . . .
C15 C 0.2512(2) 0.7803(3) 0.90898(16) 0.0171(6) Uani 1 1 d . . . . .
C16 C 0.23541(19) 0.7506(3) 0.83296(16) 0.0153(5) Uani 1 1 d . . . . .
C17 C 0.2968(2) 0.6649(4) 0.97320(17) 0.0207(6) Uani 1 1 d . . . . .
C18 C -0.0130(2) 0.7040(3) 0.90253(16) 0.0174(6) Uani 1 1 d . . . . .
C19 C 0.0812(2) 0.1921(3) 1.15592(16) 0.0170(6) Uani 1 1 d . . . . .
C20 C 0.0562(2) 0.3879(4) 0.70785(19) 0.0226(7) Uani 1 1 d . . . . .
H20 H -0.001023 0.371203 0.706551 0.027 Uiso 1 1 calc R . . . .
C21 C 0.1149(2) 0.4910(4) 0.76094(18) 0.0230(7) Uani 1 1 d . . . . .
H21 H 0.097343 0.544660 0.794627 0.028 Uiso 1 1 calc R . . . .
C22 C 0.2003(2) 0.5126(3) 0.76288(16) 0.0170(6) Uani 1 1 d . . . . .
C23 C 0.2276(2) 0.0678(3) 1.21325(18) 0.0191(6) Uani 1 1 d . . . . .
H23 H 0.286026 0.054496 1.216707 0.023 Uiso 1 1 calc R . . . .
C24 C 0.1677(2) 0.1683(3) 1.15844(16) 0.0162(6) Uani 1 1 d . . . . .
C25 C 0.1962(2) 0.2373(3) 1.09983(18) 0.0194(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sm1 O1 2.450(2) . ?
Sm1 O2 2.604(2) . ?
Sm1 O5 2.316(2) . ?
Sm1 O6 2.586(2) 3_567 ?
Sm1 O6 2.515(2) . ?
Sm1 O7 2.484(2) . ?
Sm1 O8 2.373(2) . ?
Sm1 O1W 2.533(3) . ?
Sm1 O2W 2.510(2) . ?
N1 C1 1.439(4) . ?
N1 C7 1.380(5) . ?
N1 C9 1.347(4) . ?
N2 H2 0.8600 . ?
N2 C8 1.366(5) . ?
N2 C9 1.312(5) . ?
O1 C10 1.267(4) . ?
O2 C10 1.264(4) . ?
O3 C16 1.387(3) . ?
O3 C22 1.386(3) . ?
O4 C17 1.242(4) . ?
O5 C17 1.271(4) . ?
O6 C18 1.282(3) . ?
O7 C18 1.252(4) . ?
O8 C25 1.264(4) . ?
O9 C25 1.249(4) . ?
O1W H1WA 0.8502 . ?
O1W H1WB 0.8499 . ?
O2W H2WA 0.8622 . ?
O2W H2WB 0.8519 . ?
C1 C2 1.365(6) . ?
C1 C6 1.373(5) . ?
C2 H2A 0.9300 . ?
C2 C3 1.402(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.371(6) . ?
C4 C4 1.511(7) 3_666 ?
C4 C5 1.382(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.356(5) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.499(4) 4_576 ?
C11 C12 1.401(5) . ?
C11 C16 1.397(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.380(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.382(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.388(4) . ?
C15 C16 1.396(4) . ?
C15 C17 1.510(4) . ?
C18 C19 1.496(4) 3_567 ?
C19 C20 1.402(4) 4_566 ?
C19 C24 1.400(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.383(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.384(4) . ?
C22 C23 1.390(4) 4_565 ?
C23 H23 0.9300 . ?
C23 C24 1.391(4) . ?
C24 C25 1.505(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Sm1 O2 51.73(8) . . ?
O1 Sm1 O6 84.64(8) . . ?
O1 Sm1 O6 69.34(8) . 3_567 ?
O1 Sm1 O7 129.78(8) . . ?
O1 Sm1 O1W 71.77(9) . . ?
O1 Sm1 O2W 138.46(9) . . ?
O5 Sm1 O1 130.17(8) . . ?
O5 Sm1 O2 78.88(8) . . ?
O5 Sm1 O6 146.15(8) . 3_567 ?
O5 Sm1 O6 132.60(7) . . ?
O5 Sm1 O7 80.83(8) . . ?
O5 Sm1 O8 82.82(8) . . ?
O5 Sm1 O1W 89.04(9) . . ?
O5 Sm1 O2W 85.55(9) . . ?
O6 Sm1 O2 129.76(7) . . ?
O6 Sm1 O2 109.35(7) 3_567 . ?
O6 Sm1 O6 67.90(8) . 3_567 ?
O6 Sm1 O1W 70.93(9) . . ?
O7 Sm1 O2 137.62(9) . . ?
O7 Sm1 O6 52.25(7) . . ?
O7 Sm1 O6 108.23(7) . 3_567 ?
O7 Sm1 O1W 70.55(8) . . ?
O7 Sm1 O2W 67.75(8) . . ?
O8 Sm1 O1 87.31(8) . . ?
O8 Sm1 O2 72.13(8) . . ?
O8 Sm1 O6 136.88(7) . . ?
O8 Sm1 O6 69.62(7) . 3_567 ?
O8 Sm1 O7 140.85(8) . . ?
O8 Sm1 O1W 144.40(8) . . ?
O8 Sm1 O2W 75.72(8) . . ?
O1W Sm1 O2 72.30(8) . . ?
O1W Sm1 O6 124.80(8) . 3_567 ?
O2W Sm1 O2 145.66(9) . . ?
O2W Sm1 O6 82.78(9) . . ?
O2W Sm1 O6 69.23(8) . 3_567 ?
O2W Sm1 O1W 138.29(8) . . ?
C7 N1 C1 126.5(3) . . ?
C9 N1 C1 124.8(3) . . ?
C9 N1 C7 108.3(3) . . ?
C8 N2 H2 125.0 . . ?
C9 N2 H2 125.0 . . ?
C9 N2 C8 109.9(3) . . ?
C10 O1 Sm1 95.64(18) . . ?
C10 O2 Sm1 88.59(18) . . ?
C22 O3 C16 117.8(2) . . ?
C17 O5 Sm1 142.3(2) . . ?
Sm1 O6 Sm1 112.11(8) . 3_567 ?
C18 O6 Sm1 139.25(19) . 3_567 ?
C18 O6 Sm1 91.38(18) . . ?
C18 O7 Sm1 93.59(17) . . ?
C25 O8 Sm1 122.8(2) . . ?
Sm1 O1W H1WA 117.8 . . ?
Sm1 O1W H1WB 134.5 . . ?
H1WA O1W H1WB 107.7 . . ?
Sm1 O2W H2WA 108.5 . . ?
Sm1 O2W H2WB 106.1 . . ?
H2WA O2W H2WB 106.4 . . ?
C2 C1 N1 120.0(4) . . ?
C2 C1 C6 119.8(4) . . ?
C6 C1 N1 120.2(3) . . ?
C1 C2 H2A 120.5 . . ?
C1 C2 C3 119.0(4) . . ?
C3 C2 H2A 120.5 . . ?
C2 C3 H3 118.9 . . ?
C4 C3 C2 122.2(4) . . ?
C4 C3 H3 118.9 . . ?
C3 C4 C4 122.2(5) . 3_666 ?
C3 C4 C5 117.1(4) . . ?
C5 C4 C4 120.6(5) . 3_666 ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.4(4) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 120.3(4) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
N1 C7 H7 126.7 . . ?
C8 C7 N1 106.7(3) . . ?
C8 C7 H7 126.7 . . ?
N2 C8 H8 126.5 . . ?
C7 C8 N2 107.0(3) . . ?
C7 C8 H8 126.5 . . ?
N1 C9 H9 126.0 . . ?
N2 C9 N1 108.0(3) . . ?
N2 C9 H9 126.0 . . ?
O1 C10 C11 117.7(3) . 4_576 ?
O2 C10 O1 121.6(3) . . ?
O2 C10 C11 120.5(3) . 4_576 ?
C12 C11 C10 116.5(3) . 4_575 ?
C16 C11 C10 124.7(3) . 4_575 ?
C16 C11 C12 118.7(3) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.8(3) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.7(3) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.4 . . ?
C13 C14 C15 121.2(3) . . ?
C15 C14 H14 119.4 . . ?
C14 C15 C16 118.9(3) . . ?
C14 C15 C17 117.9(3) . . ?
C16 C15 C17 123.2(3) . . ?
O3 C16 C11 120.1(2) . . ?
O3 C16 C15 119.2(3) . . ?
C15 C16 C11 120.7(3) . . ?
O4 C17 O5 124.0(3) . . ?
O4 C17 C15 119.2(3) . . ?
O5 C17 C15 116.8(3) . . ?
O6 C18 C19 120.3(3) . 3_567 ?
O7 C18 O6 120.7(3) . . ?
O7 C18 C19 118.9(3) . 3_567 ?
C20 C19 C18 118.7(3) 4_566 3_567 ?
C24 C19 C18 122.0(3) . 3_567 ?
C24 C19 C20 119.3(3) . 4_566 ?
C19 C20 H20 119.3 4_565 . ?
C21 C20 C19 121.3(3) . 4_565 ?
C21 C20 H20 119.3 . . ?
C20 C21 H21 120.7 . . ?
C20 C21 C22 118.6(3) . . ?
C22 C21 H21 120.7 . . ?
O3 C22 C23 115.5(3) . 4_565 ?
C21 C22 O3 123.2(3) . . ?
C21 C22 C23 121.3(3) . 4_565 ?
C22 C23 H23 119.9 4_566 . ?
C22 C23 C24 120.1(3) 4_566 . ?
C24 C23 H23 119.9 . . ?
C19 C24 C25 122.3(3) . . ?
C23 C24 C19 119.3(3) . . ?
C23 C24 C25 118.2(3) . . ?
O8 C25 C24 118.3(3) . . ?
O9 C25 O8 125.2(3) . . ?
O9 C25 C24 116.5(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1W H1WB O9 0.85 1.94 2.744(4) 158.0 1_565 yes
O2W H2WA O1 0.86 2.32 3.032(4) 140.1 3_567 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Sm1 O1 C10 O2 16.5(3) . . . . ?
Sm1 O1 C10 C11 -158.4(2) . . . 4_576 ?
Sm1 O2 C10 O1 -15.5(3) . . . . ?
Sm1 O2 C10 C11 159.3(3) . . . 4_576 ?
Sm1 O5 C17 O4 -121.8(4) . . . . ?
Sm1 O5 C17 C15 60.7(5) . . . . ?
Sm1 O6 C18 O7 -112.5(3) 3_567 . . . ?
Sm1 O6 C18 O7 14.7(3) . . . . ?
Sm1 O6 C18 C19 71.3(4) 3_567 . . 3_567 ?
Sm1 O6 C18 C19 -161.5(2) . . . 3_567 ?
Sm1 O7 C18 O6 -14.9(3) . . . . ?
Sm1 O7 C18 C19 161.3(2) . . . 3_567 ?
Sm1 O8 C25 O9 79.0(4) . . . . ?
Sm1 O8 C25 C24 -103.3(3) . . . . ?
N1 C1 C2 C3 -178.4(5) . . . . ?
N1 C1 C6 C5 178.3(4) . . . . ?
N1 C7 C8 N2 -0.7(4) . . . . ?
C1 N1 C7 C8 -172.5(4) . . . . ?
C1 N1 C9 N2 173.2(3) . . . . ?
C1 C2 C3 C4 -0.9(10) . . . . ?
C2 C1 C6 C5 0.3(8) . . . . ?
C2 C3 C4 C4 179.9(6) . . . 3_666 ?
C2 C3 C4 C5 2.2(9) . . . . ?
C3 C4 C5 C6 -2.3(8) . . . . ?
C4 C4 C5 C6 180.0(5) 3_666 . . . ?
C4 C5 C6 C1 1.1(8) . . . . ?
C6 C1 C2 C3 -0.4(8) . . . . ?
C7 N1 C1 C2 -134.4(5) . . . . ?
C7 N1 C1 C6 47.6(6) . . . . ?
C7 N1 C9 N2 0.2(5) . . . . ?
C8 N2 C9 N1 -0.7(5) . . . . ?
C9 N1 C1 C2 53.9(6) . . . . ?
C9 N1 C1 C6 -124.1(5) . . . . ?
C9 N1 C7 C8 0.3(4) . . . . ?
C9 N2 C8 C7 0.9(4) . . . . ?
C10 C11 C12 C13 -177.9(3) 4_575 . . . ?
C10 C11 C16 O3 -0.7(5) 4_575 . . . ?
C10 C11 C16 C15 179.2(3) 4_575 . . . ?
C11 C12 C13 C14 -1.3(6) . . . . ?
C12 C11 C16 O3 -178.2(3) . . . . ?
C12 C11 C16 C15 1.8(5) . . . . ?
C12 C13 C14 C15 1.3(6) . . . . ?
C13 C14 C15 C16 0.2(5) . . . . ?
C13 C14 C15 C17 -179.8(3) . . . . ?
C14 C15 C16 O3 178.2(3) . . . . ?
C14 C15 C16 C11 -1.8(4) . . . . ?
C14 C15 C17 O4 -137.4(3) . . . . ?
C14 C15 C17 O5 40.2(4) . . . . ?
C16 O3 C22 C21 -38.5(4) . . . . ?
C16 O3 C22 C23 143.4(3) . . . 4_565 ?
C16 C11 C12 C13 -0.2(5) . . . . ?
C16 C15 C17 O4 42.6(4) . . . . ?
C16 C15 C17 O5 -139.8(3) . . . . ?
C17 C15 C16 O3 -1.8(4) . . . . ?
C17 C15 C16 C11 178.2(3) . . . . ?
C18 C19 C24 C23 -178.8(3) 3_567 . . . ?
C18 C19 C24 C25 -3.8(4) 3_567 . . . ?
C19 C20 C21 C22 -1.0(5) 4_565 . . . ?
C19 C24 C25 O8 83.0(4) . . . . ?
C19 C24 C25 O9 -99.1(4) . . . . ?
C20 C19 C24 C23 -1.1(4) 4_566 . . . ?
C20 C19 C24 C25 173.8(3) 4_566 . . . ?
C20 C21 C22 O3 -178.5(3) . . . . ?
C20 C21 C22 C23 -0.5(5) . . . 4_565 ?
C22 O3 C16 C11 -59.8(4) . . . . ?
C22 O3 C16 C15 120.2(3) . . . . ?
C22 C23 C24 C19 2.6(5) 4_566 . . . ?
C22 C23 C24 C25 -172.6(3) 4_566 . . . ?
C23 C24 C25 O8 -102.0(3) . . . . ?
C23 C24 C25 O9 75.9(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_11563
_database_code_depnum_ccdc_archive 'CCDC 1887230'
loop_
_audit_author_name
_audit_author_address
Lirongyang
;Henan University
China
;
_audit_update_record             
;
2020-08-14 deposited with the CCDC.	2020-08-19 downloaded from the CCDC.
;
_audit_creation_date             2020-08-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H10 La O11, C9 H8 N2'
_chemical_formula_sum            'C25 H18 La N2 O11'
_chemical_formula_weight         661.32
_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'
La La -0.2871 2.4523 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.398(8)
_cell_length_b                   8.627(4)
_cell_length_c                   19.391(9)
_cell_angle_alpha                90
_cell_angle_beta                 115.01
_cell_angle_gamma                90
_cell_volume                     2486(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1051
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      19.37
_cell_measurement_theta_min      2.32
_shelx_estimated_absorpt_T_max   0.885
_shelx_estimated_absorpt_T_min   0.788
_exptl_absorpt_coefficient_mu    1.785
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6334
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0654 before and 0.0485 after correction. The Ratio of minimum to maximum transmission is 0.8494. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.767
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1308
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0996
_diffrn_reflns_av_unetI/netI     0.1340
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15227
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.428
_diffrn_reflns_theta_min         2.137
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measurement_device_type  'Bruker Smart APEX II CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3446
_reflns_number_total             5762
_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       'APEX 2'
_computing_data_collection       'APEX 2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.100
_refine_diff_density_min         -1.585
_refine_diff_density_rms         0.183
_refine_ls_extinction_coef       0.0030(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         5762
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1056
_refine_ls_R_factor_gt           0.0534
_refine_ls_restrained_S_all      0.933
_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)+(0.0371P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.1127
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All O(H,H) groups
2.a Riding coordinates:
 O1W(H1WA,H1WB), O2W(H2WA,H2WB)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C4(H4), C6(H6), C11(H11), C12(H12), C13(H13), C17(H17),
 C18(H18), C19(H19), C21(H21), C22(H22), C24(H24), C25(H25)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
La1 La 0.86535(2) 1.09040(4) 0.96277(2) 0.02072(13) Uani 1 1 d . . . . .
N1 N 0.5496(4) 0.9767(7) 0.8811(3) 0.0395(15) Uani 1 1 d . . . . .
H1 H 0.580782 1.003532 0.927690 0.047 Uiso 1 1 calc R . . . .
N2 N 0.5090(3) 0.9417(7) 0.7605(3) 0.0354(15) Uani 1 1 d . . . . .
O1 O 1.0606(3) 0.8111(5) 0.8987(2) 0.0324(12) Uani 1 1 d . . . . .
O2 O 0.9654(3) 0.8660(5) 0.9494(2) 0.0238(10) Uani 1 1 d . . . . .
O3 O 0.8082(3) 0.6485(5) 0.9509(3) 0.0431(13) Uani 1 1 d . . . . .
O4 O 0.7726(3) 0.8731(5) 0.8872(2) 0.0303(11) Uani 1 1 d . . . . .
O5 O 0.7342(3) 0.3910(5) 0.6825(2) 0.0254(10) Uani 1 1 d . . . . .
O6 O 0.6304(3) 0.4045(6) 0.5216(2) 0.0452(14) Uani 1 1 d . . . . .
O7 O 0.7291(3) 0.3453(6) 0.4746(2) 0.0345(12) Uani 1 1 d . . . . .
O8 O 0.7660(3) 0.1988(5) 0.8240(2) 0.0326(11) Uani 1 1 d . . . . .
O9 O 0.9093(3) 0.1441(5) 0.8537(3) 0.0366(12) Uani 1 1 d . . . . .
C1 C 0.9845(4) 0.7969(7) 0.8985(3) 0.0236(14) Uani 1 1 d . . . . .
C2 C 0.9169(4) 0.6929(7) 0.8411(3) 0.0225(14) Uani 1 1 d . . . . .
C3 C 0.9411(4) 0.6128(7) 0.7887(4) 0.0291(16) Uani 1 1 d . . . . .
H3 H 0.997813 0.628771 0.790057 0.035 Uiso 1 1 calc R . . . .
C4 C 0.8822(4) 0.5111(7) 0.7355(3) 0.0286(16) Uani 1 1 d . . . . .
H4 H 0.898629 0.459055 0.701285 0.034 Uiso 1 1 calc R . . . .
C5 C 0.7974(4) 0.4892(7) 0.7348(3) 0.0215(14) Uani 1 1 d . . . . .
C6 C 0.7714(4) 0.5673(7) 0.7842(3) 0.0231(14) Uani 1 1 d . . . . .
H6 H 0.713995 0.552856 0.781666 0.028 Uiso 1 1 calc R . . . .
C7 C 0.8314(4) 0.6682(7) 0.8381(3) 0.0195(14) Uani 1 1 d . . . . .
C8 C 0.8029(4) 0.7356(8) 0.8973(4) 0.0248(15) Uani 1 1 d . . . . .
C9 C 0.8284(5) 0.1674(8) 0.8042(4) 0.0314(16) Uani 1 1 d . . . . .
C10 C 0.8080(4) 0.1448(7) 0.7211(4) 0.0242(15) Uani 1 1 d . . . . .
C11 C 0.8355(5) 0.0051(8) 0.7013(4) 0.0394(19) Uani 1 1 d . . . . .
H11 H 0.867417 -0.065963 0.739240 0.047 Uiso 1 1 calc R . . . .
C12 C 0.8162(5) -0.0292(8) 0.6266(4) 0.0403(19) Uani 1 1 d . . . . .
H12 H 0.832285 -0.124747 0.613811 0.048 Uiso 1 1 calc R . . . .
C13 C 0.7728(4) 0.0795(8) 0.5710(4) 0.0307(15) Uani 1 1 d . . . . .
H13 H 0.761810 0.058190 0.520824 0.037 Uiso 1 1 calc R . . . .
C14 C 0.7450(4) 0.2213(7) 0.5888(3) 0.0231(14) Uani 1 1 d . . . . .
C15 C 0.6970(4) 0.3333(8) 0.5241(3) 0.0284(16) Uani 1 1 d . . . . .
C16 C 0.7638(4) 0.2509(7) 0.6645(3) 0.0213(14) Uani 1 1 d . . . . .
C17 C 0.5743(4) 0.9962(9) 0.8248(4) 0.0400(19) Uani 1 1 d . . . . .
H17 H 0.628042 1.040381 0.829236 0.048 Uiso 1 1 calc R . . . .
C18 C 0.4413(4) 0.8833(8) 0.7791(4) 0.0360(18) Uani 1 1 d . . . . .
H18 H 0.388130 0.836295 0.745960 0.043 Uiso 1 1 calc R . . . .
C19 C 0.4676(4) 0.9078(9) 0.8538(4) 0.0395(18) Uani 1 1 d . . . . .
H19 H 0.435365 0.882145 0.881814 0.047 Uiso 1 1 calc R . . . .
C20 C 0.5072(5) 0.9532(9) 0.6848(4) 0.045(2) Uani 1 1 d . . . . .
C21 C 0.4348(5) 1.0258(10) 0.6287(4) 0.052(2) Uani 1 1 d . . . . .
H21 H 0.387708 1.062643 0.638845 0.063 Uiso 1 1 calc R . . . .
C22 C 0.4328(5) 1.0435(10) 0.5567(4) 0.053(2) Uani 1 1 d . . . . .
H22 H 0.383187 1.091692 0.519102 0.063 Uiso 1 1 calc R . . . .
C23 C 0.5015(5) 0.9924(11) 0.5382(4) 0.050(2) Uani 1 1 d . . . . .
C24 C 0.5735(6) 0.9233(13) 0.5985(5) 0.093(4) Uani 1 1 d . . . . .
H24 H 0.621869 0.888025 0.589805 0.112 Uiso 1 1 calc R . . . .
C25 C 0.5769(5) 0.9041(13) 0.6706(5) 0.089(4) Uani 1 1 d . . . . .
H25 H 0.626702 0.857835 0.708927 0.106 Uiso 1 1 calc R . . . .
O1W O 0.9037(3) 1.3868(5) 0.9625(3) 0.0472(14) Uani 1 1 d . . . . .
H1WA H 0.960211 1.388164 0.989534 0.057 Uiso 1 1 d R . . . .
H1WB H 0.890281 1.466414 0.934094 0.057 Uiso 1 1 d R . . . .
O2W O 0.8895(3) 0.8725(5) 1.0623(3) 0.0455(14) Uani 1 1 d . . . . .
H2WA H 0.916936 0.832810 1.106236 0.055 Uiso 1 1 d R . . . .
H2WB H 0.866086 0.798900 1.030906 0.055 Uiso 1 1 d R . . . .


_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
La1 O1 2.579(4) 3_777 ?
La1 O2 2.620(4) . ?
La1 O2 2.597(4) 3_777 ?
La1 O4 2.468(4) . ?
La1 O7 2.405(4) 4_576 ?
La1 O8 2.657(4) 1_565 ?
La1 O9 2.550(5) 1_565 ?
La1 C1 2.940(6) 3_777 ?
La1 C9 2.948(7) 1_565 ?
La1 O1W 2.633(5) . ?
La1 O2W 2.601(5) . ?
N1 H1 0.8600 . ?
N1 C17 1.326(8) . ?
N1 C19 1.357(8) . ?
N2 C17 1.340(8) . ?
N2 C18 1.398(8) . ?
N2 C20 1.459(9) . ?
O1 C1 1.252(7) . ?
O2 C1 1.299(7) . ?
O3 C8 1.256(7) . ?
O4 C8 1.269(7) . ?
O5 C5 1.390(7) . ?
O5 C16 1.402(7) . ?
O6 C15 1.236(7) . ?
O7 C15 1.280(7) . ?
O8 C9 1.266(7) . ?
O9 C9 1.283(7) . ?
C1 C2 1.494(8) . ?
C2 C3 1.416(8) . ?
C2 C7 1.396(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.388(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.398(8) . ?
C5 C6 1.378(8) . ?
C6 H6 0.9300 . ?
C6 C7 1.395(8) . ?
C7 C8 1.525(8) . ?
C9 C10 1.513(9) . ?
C10 C11 1.396(9) . ?
C10 C16 1.377(8) . ?
C11 H11 0.9300 . ?
C11 C12 1.379(9) . ?
C12 H12 0.9300 . ?
C12 C13 1.378(9) . ?
C13 H13 0.9300 . ?
C13 C14 1.399(8) . ?
C14 C15 1.515(8) . ?
C14 C16 1.389(8) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C18 C19 1.342(9) . ?
C19 H19 0.9300 . ?
C20 C21 1.375(9) . ?
C20 C25 1.351(10) . ?
C21 H21 0.9300 . ?
C21 C22 1.392(10) . ?
C22 H22 0.9300 . ?
C22 C23 1.390(10) . ?
C23 C23 1.468(14) 3_676 ?
C23 C24 1.396(11) . ?
C24 H24 0.9300 . ?
C24 C25 1.385(11) . ?
C25 H25 0.9300 . ?
O1W H1WA 0.8499 . ?
O1W H1WB 0.8499 . ?
O2W H2WA 0.8500 . ?
O2W H2WB 0.8501 . ?

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 La1 O2 50.76(13) 3_777 3_777 ?
O1 La1 O2 107.90(13) 3_777 . ?
O1 La1 O8 139.07(15) 3_777 1_565 ?
O1 La1 C1 25.15(14) 3_777 3_777 ?
O1 La1 C9 144.16(18) 3_777 1_565 ?
O1 La1 O1W 70.98(15) 3_777 . ?
O1 La1 O2W 66.98(15) 3_777 . ?
O2 La1 O2 68.38(14) 3_777 . ?
O2 La1 O8 107.55(13) . 1_565 ?
O2 La1 O8 129.83(14) 3_777 1_565 ?
O2 La1 C1 26.22(14) 3_777 3_777 ?
O2 La1 C1 90.99(16) . 3_777 ?
O2 La1 C9 110.04(16) 3_777 1_565 ?
O2 La1 C9 85.67(16) . 1_565 ?
O2 La1 O1W 123.85(14) . . ?
O2 La1 O1W 70.78(14) 3_777 . ?
O2 La1 O2W 80.40(14) 3_777 . ?
O4 La1 O1 140.30(15) . 3_777 ?
O4 La1 O2 135.95(13) . 3_777 ?
O4 La1 O2 68.58(13) . . ?
O4 La1 O8 72.90(15) . 1_565 ?
O4 La1 O9 87.98(15) . 1_565 ?
O4 La1 C1 149.55(16) . 3_777 ?
O4 La1 C9 75.42(17) . 1_565 ?
O4 La1 O1W 145.50(15) . . ?
O4 La1 O2W 75.75(15) . . ?
O7 La1 O1 82.67(14) 4_576 3_777 ?
O7 La1 O2 145.64(15) 4_576 . ?
O7 La1 O2 133.03(14) 4_576 3_777 ?
O7 La1 O4 82.38(15) 4_576 . ?
O7 La1 O8 79.55(14) 4_576 1_565 ?
O7 La1 O9 129.57(15) 4_576 1_565 ?
O7 La1 C1 106.81(17) 4_576 3_777 ?
O7 La1 C9 104.94(17) 4_576 1_565 ?
O7 La1 O1W 90.49(16) 4_576 . ?
O7 La1 O2W 87.26(16) 4_576 . ?
O8 La1 C1 136.70(16) 1_565 3_777 ?
O8 La1 C9 25.42(14) 1_565 1_565 ?
O9 La1 O1 129.07(15) 1_565 3_777 ?
O9 La1 O2 85.36(14) 1_565 3_777 ?
O9 La1 O2 69.13(14) 1_565 . ?
O9 La1 O8 50.45(14) 1_565 1_565 ?
O9 La1 C1 106.13(17) 1_565 3_777 ?
O9 La1 C9 25.69(15) 1_565 1_565 ?
O9 La1 O1W 70.77(15) 1_565 . ?
O9 La1 O2W 137.65(15) 1_565 . ?
C1 La1 C9 127.10(18) 3_777 1_565 ?
O1W La1 O8 72.61(14) . 1_565 ?
O1W La1 C1 64.68(15) . 3_777 ?
O1W La1 C9 73.95(17) . 1_565 ?
O2W La1 O2 68.54(14) . . ?
O2W La1 O8 147.26(15) . 1_565 ?
O2W La1 C1 75.79(16) . 3_777 ?
O2W La1 C9 146.74(17) . 1_565 ?
O2W La1 O1W 137.85(15) . . ?
C17 N1 H1 125.3 . . ?
C17 N1 C19 109.4(6) . . ?
C19 N1 H1 125.3 . . ?
C17 N2 C18 107.1(6) . . ?
C17 N2 C20 125.5(6) . . ?
C18 N2 C20 127.2(6) . . ?
C1 O1 La1 93.7(4) . 3_777 ?
La1 O2 La1 111.62(14) 3_777 . ?
C1 O2 La1 91.8(3) . 3_777 ?
C1 O2 La1 140.9(4) . . ?
C8 O4 La1 121.0(4) . . ?
C5 O5 C16 118.5(4) . . ?
C15 O7 La1 141.6(4) . 4_575 ?
C9 O8 La1 90.2(4) . 1_545 ?
C9 O9 La1 94.8(4) . 1_545 ?
O1 C1 La1 61.1(3) . 3_777 ?
O1 C1 O2 120.8(6) . . ?
O1 C1 C2 119.0(6) . . ?
O2 C1 La1 62.0(3) . 3_777 ?
O2 C1 C2 120.1(5) . . ?
C2 C1 La1 162.1(4) . 3_777 ?
C3 C2 C1 118.9(6) . . ?
C7 C2 C1 122.6(6) . . ?
C7 C2 C3 118.5(6) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.6(6) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 121.0 . . ?
C3 C4 C5 118.0(6) . . ?
C5 C4 H4 121.0 . . ?
O5 C5 C4 121.4(5) . . ?
C6 C5 O5 116.9(5) . . ?
C6 C5 C4 121.7(5) . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 119.9(6) . . ?
C7 C6 H6 120.0 . . ?
C2 C7 C8 122.2(5) . . ?
C6 C7 C2 120.2(6) . . ?
C6 C7 C8 117.3(5) . . ?
O3 C8 O4 124.9(6) . . ?
O3 C8 C7 117.3(6) . . ?
O4 C8 C7 117.7(6) . . ?
O8 C9 La1 64.3(3) . 1_545 ?
O8 C9 O9 121.3(6) . . ?
O8 C9 C10 120.5(6) . . ?
O9 C9 La1 59.5(3) . 1_545 ?
O9 C9 C10 118.0(6) . . ?
C10 C9 La1 159.6(4) . 1_545 ?
C11 C10 C9 116.9(6) . . ?
C16 C10 C9 124.7(6) . . ?
C16 C10 C11 118.5(6) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.1(7) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 120.4 . . ?
C13 C12 C11 119.3(7) . . ?
C13 C12 H12 120.4 . . ?
C12 C13 H13 119.4 . . ?
C12 C13 C14 121.1(6) . . ?
C14 C13 H13 119.4 . . ?
C13 C14 C15 117.6(6) . . ?
C16 C14 C13 118.1(6) . . ?
C16 C14 C15 124.3(6) . . ?
O6 C15 O7 124.6(6) . . ?
O6 C15 C14 119.4(6) . . ?
O7 C15 C14 116.0(6) . . ?
C10 C16 O5 119.7(6) . . ?
C10 C16 C14 121.8(6) . . ?
C14 C16 O5 118.5(5) . . ?
N1 C17 N2 108.7(6) . . ?
N1 C17 H17 125.7 . . ?
N2 C17 H17 125.7 . . ?
N2 C18 H18 126.4 . . ?
C19 C18 N2 107.2(6) . . ?
C19 C18 H18 126.4 . . ?
N1 C19 H19 126.2 . . ?
C18 C19 N1 107.6(6) . . ?
C18 C19 H19 126.2 . . ?
C21 C20 N2 118.0(7) . . ?
C25 C20 N2 121.6(7) . . ?
C25 C20 C21 120.3(8) . . ?
C20 C21 H21 120.4 . . ?
C20 C21 C22 119.3(7) . . ?
C22 C21 H21 120.4 . . ?
C21 C22 H22 118.5 . . ?
C23 C22 C21 123.1(7) . . ?
C23 C22 H22 118.5 . . ?
C22 C23 C23 123.1(9) . 3_676 ?
C22 C23 C24 114.2(7) . . ?
C24 C23 C23 122.7(9) . 3_676 ?
C23 C24 H24 118.1 . . ?
C25 C24 C23 123.8(8) . . ?
C25 C24 H24 118.1 . . ?
C20 C25 C24 119.4(8) . . ?
C20 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
La1 O1W H1WA 102.2 . . ?
La1 O1W H1WB 142.1 . . ?
H1WA O1W H1WB 107.7 . . ?
La1 O2W H2WA 152.3 . . ?
La1 O2W H2WB 97.4 . . ?
H2WA O2W H2WB 107.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C4 H4 O1 0.93 2.63 3.563(8) 178.1 2_746 yes
C17 H17 O4 0.93 2.59 3.136(8) 118.0 . yes
C18 H18 O8 0.93 2.60 3.513(8) 169.2 2_656 yes
C19 H19 O5 0.93 2.52 3.081(8) 118.9 2_656 yes
C19 H19 O6 0.93 2.53 3.420(8) 159.7 2_656 yes
O1W H1WA O2 0.85 2.54 3.029(6) 117.2 3_777 yes
O1W H1WB O3 0.85 2.18 2.703(7) 119.5 1_565 yes
O2W H2WB O3 0.85 1.93 2.781(6) 173.7 . yes
O2W H2WB O4 0.85 2.63 3.114(6) 117.4 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
La1 O1 C1 O2 17.5(6) 3_777 . . . ?
La1 O1 C1 C2 -159.5(5) 3_777 . . . ?
La1 O2 C1 La1 128.5(6) . . . 3_777 ?
La1 O2 C1 O1 111.1(6) . . . . ?
La1 O2 C1 O1 -17.4(6) 3_777 . . . ?
La1 O2 C1 C2 159.6(5) 3_777 . . . ?
La1 O2 C1 C2 -71.9(8) . . . . ?
La1 O4 C8 O3 78.3(7) . . . . ?
La1 O4 C8 C7 -104.4(5) . . . . ?
La1 O7 C15 O6 122.9(7) 4_575 . . . ?
La1 O7 C15 C14 -57.9(9) 4_575 . . . ?
La1 O8 C9 O9 -18.1(7) 1_545 . . . ?
La1 O8 C9 C10 157.5(6) 1_545 . . . ?
La1 O9 C9 O8 19.0(7) 1_545 . . . ?
La1 O9 C9 C10 -156.7(5) 1_545 . . . ?
La1 C1 C2 C3 -85.2(15) 3_777 . . . ?
La1 C1 C2 C7 93.1(15) 3_777 . . . ?
La1 C9 C10 C11 -26.3(16) 1_545 . . . ?
La1 C9 C10 C16 153.0(10) 1_545 . . . ?
N2 C18 C19 N1 -1.0(8) . . . . ?
N2 C20 C21 C22 177.7(7) . . . . ?
N2 C20 C25 C24 -177.4(9) . . . . ?
O1 C1 C2 C3 0.3(9) . . . . ?
O1 C1 C2 C7 178.5(6) . . . . ?
O2 C1 C2 C3 -176.8(6) . . . . ?
O2 C1 C2 C7 1.5(9) . . . . ?
O5 C5 C6 C7 -179.8(5) . . . . ?
O8 C9 C10 C11 -124.6(7) . . . . ?
O8 C9 C10 C16 54.7(10) . . . . ?
O9 C9 C10 C11 51.2(9) . . . . ?
O9 C9 C10 C16 -129.6(7) . . . . ?
C1 C2 C3 C4 178.1(6) . . . . ?
C1 C2 C7 C6 -178.7(6) . . . . ?
C1 C2 C7 C8 -4.9(9) . . . . ?
C2 C3 C4 C5 -0.1(10) . . . . ?
C2 C7 C8 O3 -97.4(7) . . . . ?
C2 C7 C8 O4 85.2(7) . . . . ?
C3 C2 C7 C6 -0.4(9) . . . . ?
C3 C2 C7 C8 173.4(6) . . . . ?
C3 C4 C5 O5 179.1(6) . . . . ?
C3 C4 C5 C6 1.1(9) . . . . ?
C4 C5 C6 C7 -1.8(9) . . . . ?
C5 O5 C16 C10 59.1(7) . . . . ?
C5 O5 C16 C14 -122.9(6) . . . . ?
C5 C6 C7 C2 1.4(9) . . . . ?
C5 C6 C7 C8 -172.7(6) . . . . ?
C6 C7 C8 O3 76.6(7) . . . . ?
C6 C7 C8 O4 -100.8(7) . . . . ?
C7 C2 C3 C4 -0.3(9) . . . . ?
C9 C10 C11 C12 176.9(7) . . . . ?
C9 C10 C16 O5 -0.3(9) . . . . ?
C9 C10 C16 C14 -178.2(6) . . . . ?
C10 C11 C12 C13 3.2(11) . . . . ?
C11 C10 C16 O5 179.0(5) . . . . ?
C11 C10 C16 C14 1.0(9) . . . . ?
C11 C12 C13 C14 -2.5(11) . . . . ?
C12 C13 C14 C15 -179.4(6) . . . . ?
C12 C13 C14 C16 1.1(9) . . . . ?
C13 C14 C15 O6 137.9(7) . . . . ?
C13 C14 C15 O7 -41.4(8) . . . . ?
C13 C14 C16 O5 -178.4(5) . . . . ?
C13 C14 C16 C10 -0.4(9) . . . . ?
C15 C14 C16 O5 2.2(9) . . . . ?
C15 C14 C16 C10 -179.8(6) . . . . ?
C16 O5 C5 C4 39.5(8) . . . . ?
C16 O5 C5 C6 -142.4(6) . . . . ?
C16 C10 C11 C12 -2.4(10) . . . . ?
C16 C14 C15 O6 -42.7(9) . . . . ?
C16 C14 C15 O7 138.0(6) . . . . ?
C17 N1 C19 C18 0.4(9) . . . . ?
C17 N2 C18 C19 1.3(8) . . . . ?
C17 N2 C20 C21 -122.5(8) . . . . ?
C17 N2 C20 C25 53.0(12) . . . . ?
C18 N2 C17 N1 -1.0(8) . . . . ?
C18 N2 C20 C21 52.4(11) . . . . ?
C18 N2 C20 C25 -132.0(9) . . . . ?
C19 N1 C17 N2 0.4(9) . . . . ?
C20 N2 C17 N1 174.7(6) . . . . ?
C20 N2 C18 C19 -174.4(7) . . . . ?
C20 C21 C22 C23 -0.7(14) . . . . ?
C21 C20 C25 C24 -2.0(16) . . . . ?
C21 C22 C23 C23 178.4(10) . . . 3_676 ?
C21 C22 C23 C24 -0.7(14) . . . . ?
C22 C23 C24 C25 0.8(16) . . . . ?
C23 C23 C24 C25 -178.3(12) 3_676 . . . ?
C23 C24 C25 C20 0.5(19) . . . . ?
C25 C20 C21 C22 2.1(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
