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

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

data_SUM-6
_database_code_depnum_ccdc_archive 'CCDC 2159905'
loop_
_audit_author_name
_audit_author_address
'Chong Liu'
;Sichuan University
China
;
_audit_update_record             
;
2022-03-18 deposited with the CCDC.	2022-11-09 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT241_SUM-6               
;
PROBLEM: High   'MainMol' Ueq as Compared to Neighbors of         C6 Check
RESPONSE: C6 is a terminal atom of a coordinating solvent molecule with possible severe disorders or thermal motions.
;
# Added during the CSD deposition process: Friday 18 March 2022 07:32 AM
# end Validation Reply Form

_audit_creation_date             2022-03-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H20 Ce N5 O9'
_chemical_formula_sum            'C14 H20 Ce N5 O9'
_chemical_formula_weight         542.47
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   13.9892(7)
_cell_length_b                   20.1086(9)
_cell_length_c                   8.5463(4)
_cell_angle_alpha                90
_cell_angle_beta                 124.703(2)
_cell_angle_gamma                90
_cell_volume                     1976.44(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5738
_cell_measurement_temperature    304(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      3.52
_shelx_estimated_absorpt_T_max   0.871
_shelx_estimated_absorpt_T_min   0.798
_exptl_absorpt_coefficient_mu    2.361
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6536
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0728 before and 0.0622 after correction.
The Ratio of minimum to maximum transmission is 0.8766.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.823
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1076
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0708
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            15794
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_min         2.026
_diffrn_ambient_temperature      304.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1966
_reflns_number_total             2267
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.406
_refine_diff_density_min         -1.014
_refine_diff_density_rms         0.155
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         2267
_refine_ls_number_restraints     27
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0418
_refine_ls_restrained_S_all      1.167
_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)+(0.0650P)²+6.2932P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1088
_refine_ls_wR_factor_ref         0.1137
_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 C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Ce1 \\sim O3: within 3A with sigma of 0.01 and sigma for terminal atoms of
0.015 within 3A
N3 \\sim C6 \\sim C7: within 3A with sigma of 0.01 and sigma for terminal atoms
of 0.015 within 3A
3. Rigid body (RIGU) restrains
 N3, C7
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(O6)=1-FVAR(1)
 Sof(O5)=FVAR(1)
 Sof(C5B)=Sof(H5B)=1-FVAR(2)
 Sof(C5A)=Sof(H5A)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C5A(H5A), C5B(H5B)
5.b Idealised Me refined with riding coordinates:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ce1 Ce 0.500000 0.51343(2) 0.250000 0.02757(16) Uani 1 2 d S TU P C .
O1 O 0.7009(5) 0.5592(4) 0.3928(9) 0.0842(19) Uani 1 1 d . . . . .
O2 O 0.5706(4) 0.54958(17) 0.5757(5) 0.0387(9) Uani 1 1 d . . . . .
N1 N 0.6223(5) 0.6090(2) 0.6555(6) 0.0437(12) Uani 1 1 d . . . . .
H1 H 0.637445 0.636732 0.595778 0.052 Uiso 1 1 calc R U . . .
O4 O 0.6281(5) 0.5830(2) 0.9154(6) 0.0546(12) Uani 1 1 d . . . . .
O3 O 0.500000 0.6442(4) 0.250000 0.097(3) Uani 1 2 d S TU P . .
C3 C 0.6484(6) 0.6230(3) 0.8260(8) 0.0455(14) Uani 1 1 d . . . . .
C4 C 0.7021(6) 0.6893(3) 0.9115(8) 0.0482(16) Uani 1 1 d . . . . .
C1 C 0.8184(7) 0.7846(3) 0.9576(10) 0.0580(19) Uani 1 1 d . . . . .
H1A H 0.865084 0.807642 0.930734 0.070 Uiso 1 1 calc R U . . .
C2 C 0.7691(7) 0.7247(3) 0.8689(10) 0.0583(19) Uani 1 1 d . . . . .
H2 H 0.781069 0.708143 0.779803 0.070 Uiso 1 1 calc R U . . .
N2 N 0.500000 0.6998(4) 0.250000 0.098(4) Uani 1 2 d S T P B .
N3 N 0.8576(8) 0.5872(5) 0.4028(16) 0.106(3) Uani 1 1 d . U . . .
C6 C 0.8607(19) 0.5259(10) 0.304(3) 0.199(7) Uani 1 1 d . U . . .
H6A H 0.929078 0.526954 0.302838 0.299 Uiso 1 1 calc R U . A 2
H6B H 0.792815 0.524925 0.175054 0.299 Uiso 1 1 calc R U . A 2
H6C H 0.862303 0.486925 0.369847 0.299 Uiso 1 1 calc R U . A 2
C7 C 0.9372(13) 0.6259(9) 0.395(2) 0.175(5) Uani 1 1 d . U . . .
H7A H 1.012686 0.605621 0.471050 0.262 Uiso 1 1 calc R U . . .
H7B H 0.940476 0.669482 0.444101 0.262 Uiso 1 1 calc R U . . .
H7C H 0.913511 0.629390 0.265896 0.262 Uiso 1 1 calc R U . . .
O5 O 0.483(6) 0.7357(11) 0.121(4) 0.120(17) Uani 0.42(7) 1 d . . P B 1
O6 O 0.394(4) 0.7183(17) 0.096(2) 0.125(16) Uani 0.58(7) 1 d . . P B 2
C5A C 0.7601(12) 0.5508(9) 0.338(2) 0.053(5) Uani 0.47(2) 1 d . . P C 1
H5A H 0.739523 0.518005 0.247344 0.063 Uiso 0.47(2) 1 calc R U P C 1
C5B C 0.7764(16) 0.6034(12) 0.417(3) 0.086(7) Uani 0.53(2) 1 d . . P C 2
H5B H 0.770098 0.647172 0.446056 0.104 Uiso 0.53(2) 1 calc R U P C 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ce1 O1 2.516(6) . ?
Ce1 O1 2.516(6) 2_655 ?
Ce1 O2 2.474(3) 2_655 ?
Ce1 O2 2.474(3) . ?
Ce1 O2 2.545(4) 6_565 ?
Ce1 O2 2.545(4) 5_666 ?
Ce1 O4 2.467(4) 5_666 ?
Ce1 O4 2.467(4) 6_565 ?
Ce1 O3 2.629(8) . ?
O1 C5A 1.171(16) . ?
O1 C5B 1.303(19) . ?
O2 N1 1.362(5) . ?
N1 H1 0.8600 . ?
N1 C3 1.315(7) . ?
O4 C3 1.249(7) . ?
O3 N2 1.118(11) . ?
C3 C4 1.499(8) . ?
C4 C1 1.405(9) 7_667 ?
C4 C2 1.381(9) . ?
C1 H1A 0.9300 . ?
C1 C2 1.380(8) . ?
C2 H2 0.9300 . ?
N2 O5 1.22(2) 2_655 ?
N2 O5 1.22(2) . ?
N2 O6 1.36(3) 2_655 ?
N2 O6 1.36(3) . ?
N3 C6 1.51(2) . ?
N3 C7 1.390(15) . ?
N3 C5A 1.358(17) . ?
N3 C5B 1.26(2) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C5A H5A 0.9300 . ?
C5B H5B 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
O1 Ce1 O1 137.1(3) 2_655 . ?
O1 Ce1 O2 126.64(18) . 5_666 ?
O1 Ce1 O2 76.55(18) . 6_565 ?
O1 Ce1 O2 76.55(18) 2_655 5_666 ?
O1 Ce1 O2 126.64(18) 2_655 6_565 ?
O1 Ce1 O3 68.55(17) . . ?
O1 Ce1 O3 68.55(18) 2_655 . ?
O2 Ce1 O1 74.15(18) 2_655 2_655 ?
O2 Ce1 O1 93.34(18) . 2_655 ?
O2 Ce1 O1 93.34(19) 2_655 . ?
O2 Ce1 O1 74.15(18) . . ?
O2 Ce1 O2 120.27(16) 6_565 5_666 ?
O2 Ce1 O2 61.77(13) . 5_666 ?
O2 Ce1 O2 145.82(17) . 2_655 ?
O2 Ce1 O2 139.96(17) 2_655 5_666 ?
O2 Ce1 O2 61.77(13) 2_655 6_565 ?
O2 Ce1 O2 139.96(17) . 6_565 ?
O2 Ce1 O3 119.86(8) 6_565 . ?
O2 Ce1 O3 119.86(8) 5_666 . ?
O2 Ce1 O3 72.91(8) . . ?
O2 Ce1 O3 72.91(8) 2_655 . ?
O4 Ce1 O1 144.3(2) 6_565 2_655 ?
O4 Ce1 O1 76.3(2) 6_565 . ?
O4 Ce1 O1 76.3(2) 5_666 2_655 ?
O4 Ce1 O1 144.3(2) 5_666 . ?
O4 Ce1 O2 83.79(13) 5_666 2_655 ?
O4 Ce1 O2 70.74(15) 6_565 5_666 ?
O4 Ce1 O2 63.06(12) 5_666 5_666 ?
O4 Ce1 O2 124.77(12) 5_666 . ?
O4 Ce1 O2 63.06(12) 6_565 6_565 ?
O4 Ce1 O2 83.79(13) 6_565 . ?
O4 Ce1 O2 124.77(12) 6_565 2_655 ?
O4 Ce1 O2 70.74(15) 5_666 6_565 ?
O4 Ce1 O4 76.3(2) 5_666 6_565 ?
O4 Ce1 O3 141.83(12) 6_565 . ?
O4 Ce1 O3 141.83(12) 5_666 . ?
C5A O1 Ce1 127.0(9) . . ?
C5B O1 Ce1 155.1(11) . . ?
Ce1 O2 Ce1 118.23(13) . 5_666 ?
N1 O2 Ce1 125.4(3) . . ?
N1 O2 Ce1 114.6(3) . 5_666 ?
O2 N1 H1 120.8 . . ?
C3 N1 O2 118.5(4) . . ?
C3 N1 H1 120.8 . . ?
C3 O4 Ce1 120.0(3) . 5_666 ?
N2 O3 Ce1 180.0 . . ?
N1 C3 C4 118.5(5) . . ?
O4 C3 N1 121.6(5) . . ?
O4 C3 C4 120.0(5) . . ?
C1 C4 C3 116.6(6) 7_667 . ?
C2 C4 C3 123.9(6) . . ?
C2 C4 C1 119.5(5) . 7_667 ?
C4 C1 H1A 120.0 7_667 . ?
C2 C1 C4 119.9(6) . 7_667 ?
C2 C1 H1A 120.0 . . ?
C4 C2 H2 119.7 . . ?
C1 C2 C4 120.5(6) . . ?
C1 C2 H2 119.7 . . ?
O3 N2 O5 126.3(12) . . ?
O3 N2 O5 126.3(12) . 2_655 ?
O3 N2 O6 105.9(18) . 2_655 ?
O3 N2 O6 105.9(18) . . ?
O5 N2 O5 107(2) 2_655 . ?
O5 N2 O6 54.2(16) 2_655 2_655 ?
O5 N2 O6 105(3) . 2_655 ?
O6 N2 O6 148(4) . 2_655 ?
C7 N3 C6 98.7(13) . . ?
C5A N3 C6 71.1(13) . . ?
C5A N3 C7 158.3(13) . . ?
C5B N3 C6 125.9(16) . . ?
C5B N3 C7 130.7(16) . . ?
N3 C6 H6A 109.5 . . ?
N3 C6 H6B 109.5 . . ?
N3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N3 C7 H7A 109.5 . . ?
N3 C7 H7B 109.5 . . ?
N3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C5A N3 122.3(15) . . ?
O1 C5A H5A 118.8 . . ?
N3 C5A H5A 118.8 . . ?
O1 C5B H5B 120.0 . . ?
N3 C5B O1 120(2) . . ?
N3 C5B H5B 120.0 . . ?

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 C5A N3 167.5(9) . . . . ?
Ce1 O1 C5B N3 -128(2) . . . . ?
Ce1 O2 N1 C3 175.6(5) . . . . ?
Ce1 O2 N1 C3 11.2(7) 5_666 . . . ?
Ce1 O4 C3 N1 -13.3(9) 5_666 . . . ?
Ce1 O4 C3 C4 165.7(5) 5_666 . . . ?
O2 N1 C3 O4 0.8(10) . . . . ?
O2 N1 C3 C4 -178.2(6) . . . . ?
N1 C3 C4 C1 152.1(7) . . . 7_667 ?
N1 C3 C4 C2 -28.0(11) . . . . ?
O4 C3 C4 C1 -26.9(10) . . . 7_667 ?
O4 C3 C4 C2 152.9(8) . . . . ?
C3 C4 C2 C1 -178.2(7) . . . . ?
C4 C1 C2 C4 -1.7(13) 7_667 . . . ?
C1 C4 C2 C1 1.7(13) 7_667 . . . ?
C6 N3 C5A O1 163.9(18) . . . . ?
C6 N3 C5B O1 19(3) . . . . ?
C7 N3 C5A O1 -131(3) . . . . ?
C7 N3 C5B O1 169.6(15) . . . . ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_SUM-7
_database_code_depnum_ccdc_archive 'CCDC 2159906'
loop_
_audit_author_name
_audit_author_address
'Chong Liu'
;Sichuan University
China
;
_audit_update_record             
;
2022-03-18 deposited with the CCDC.	2022-11-09 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT250_SUM-7               
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        4.6 Note
RESPONSE: This is due to the structure containing highly disordered components in the acetate as well as the benzene ring.
;
# Added during the CSD deposition process: Friday 18 March 2022 07:32 AM
# end Validation Reply Form

_audit_creation_date             2022-03-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H9 Ce N2 O6'
_chemical_formula_sum            'C10 H9 Ce N2 O6'
_chemical_formula_weight         393.31
_chemical_absolute_configuration ?
_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      tetragonal
_space_group_IT_number           98
_space_group_name_H-M_alt        'I 41 2 2'
_space_group_name_Hall           'I 4bw 2bw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-y, x+1/2, z+1/4'
'y+1/2, -x, z+3/4'
'-x+1/2, y, -z+3/4'
'x, -y+1/2, -z+1/4'
'y+1/2, x+1/2, -z+1/2'
'-y, -x, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1, z+1'
'-y+1/2, x+1, z+3/4'
'y+1, -x+1/2, z+5/4'
'-x+1, y+1/2, -z+5/4'
'x+1/2, -y+1, -z+3/4'
'y+1, x+1, -z+1'
'-y+1/2, -x+1/2, -z+1/2'

_cell_length_a                   17.450(3)
_cell_length_b                   17.450(3)
_cell_length_c                   16.295(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4961(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9939
_cell_measurement_temperature    304(2)
_cell_measurement_theta_max      27.396
_cell_measurement_theta_min      2.333
_shelx_estimated_absorpt_T_max   0.851
_shelx_estimated_absorpt_T_min   0.504
_exptl_absorpt_coefficient_mu    1.847
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5343
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.053
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1512
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1090
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            101387
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.624
_diffrn_reflns_theta_min         2.334
_diffrn_ambient_temperature      304.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                2633
_reflns_number_total             2891
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.067
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.116
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.50(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     94
_refine_ls_number_reflns         2891
_refine_ls_number_restraints     27
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0307
_refine_ls_restrained_S_all      1.077
_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)+(0.0624P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0800
_refine_ls_wR_factor_ref         0.0820
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.50(2)
 0.50(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Rigid bond restraints
 C2, C3, C4
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C2 \\sim C3 \\sim C4: within 2A with sigma of 0.04 and sigma for terminal atoms
of 0.08 within 2A
Uanis(C3) \\sim Ueq, Uanis(C6) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
5. Others
 Fixed Sof: C6(0.5) H6A(0.5) H6B(0.5) H6C(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C4(H4)
6.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ce1 Ce 0.250000 0.73130(2) 0.375000 0.02417(14) Uani 1 2 d S T P . .
O1 O 0.3271(2) 0.7780(2) 0.49000(19) 0.0338(9) Uani 1 1 d . . . . .
N1 N 0.3742(3) 0.8398(3) 0.4855(3) 0.0440(15) Uani 1 1 d . . . . .
H1 H 0.391002 0.855479 0.438824 0.053 Uiso 1 1 calc R U . . .
O2 O 0.3674(2) 0.8532(2) 0.62116(19) 0.0524(13) Uani 1 1 d . . . . .
O3 O 0.3398(3) 0.8301(3) 0.3182(2) 0.067(2) Uani 1 1 d . . . . .
C1 C 0.3935(4) 0.8750(4) 0.5529(4) 0.0409(13) Uani 1 1 d . . . . .
C2 C 0.4491(4) 0.9375(4) 0.5467(4) 0.057(2) Uani 1 1 d . U . . .
C3 C 0.4743(4) 0.9692(4) 0.6167(3) 0.062(2) Uani 1 1 d . U . . .
H3 H 0.457126 0.949772 0.666580 0.074 Uiso 1 1 calc R U . . .
C5 C 0.3568(4) 0.8568(4) 0.250000 0.076(5) Uani 1 2 d S T P . .
C4 C 0.4670(7) 0.9726(7) 0.4781(4) 0.136(6) Uani 1 1 d . U . . .
H4 H 0.439138 0.963674 0.430403 0.163 Uiso 1 1 calc R U . . .
C6 C 0.4399(10) 0.8969(12) 0.2469(13) 0.087(6) Uani 0.5 1 d . U P . .
H6A H 0.442167 0.937130 0.286912 0.130 Uiso 0.5 1 calc R U P . .
H6B H 0.448353 0.917882 0.193171 0.130 Uiso 0.5 1 calc R U P . .
H6C H 0.478698 0.859425 0.258603 0.130 Uiso 0.5 1 calc R U P . .


_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 Ce1 4.0997(10) 4_464 ?
Ce1 Ce1 4.0997(10) 3_655 ?
Ce1 O1 2.473(3) 8_666 ?
Ce1 O1 2.473(3) 4_464 ?
Ce1 O1 2.447(3) . ?
Ce1 O1 2.447(3) 5 ?
Ce1 O2 2.492(4) 8_666 ?
Ce1 O2 2.492(4) 4_464 ?
Ce1 O3 2.508(4) . ?
Ce1 O3 2.508(4) 5 ?
O1 N1 1.358(6) . ?
N1 H1 0.8600 . ?
N1 C1 1.303(7) . ?
O2 C1 1.261(6) . ?
O3 C5 1.240(5) . ?
C1 C2 1.464(8) . ?
C2 C3 1.342(7) . ?
C2 C4 1.312(9) . ?
C3 C3 1.399(15) 10_564 ?
C3 H3 0.9300 . ?
C5 C6 1.611(16) . ?
C5 C6 1.611(16) 7_455 ?
C4 C4 1.497(15) 10_564 ?
C4 H4 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6A 0.96(5) 7_455 ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?

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
Ce1 Ce1 Ce1 170.869(10) 3_655 4_464 ?
O1 Ce1 Ce1 154.28(8) 8_666 4_464 ?
O1 Ce1 Ce1 33.36(8) 4_464 4_464 ?
O1 Ce1 Ce1 33.77(8) 5 4_464 ?
O1 Ce1 Ce1 141.11(9) 5 3_655 ?
O1 Ce1 Ce1 33.77(8) . 3_655 ?
O1 Ce1 Ce1 141.11(9) . 4_464 ?
O1 Ce1 Ce1 33.36(8) 8_666 3_655 ?
O1 Ce1 Ce1 154.28(8) 4_464 3_655 ?
O1 Ce1 O1 141.1(2) . 5 ?
O1 Ce1 O1 64.18(15) 5 4_464 ?
O1 Ce1 O1 64.18(15) . 8_666 ?
O1 Ce1 O1 135.23(10) 5 8_666 ?
O1 Ce1 O1 135.23(10) . 4_464 ?
O1 Ce1 O1 131.30(17) 4_464 8_666 ?
O1 Ce1 O2 127.46(11) 5 4_464 ?
O1 Ce1 O2 83.10(13) 4_464 8_666 ?
O1 Ce1 O2 83.10(13) 8_666 4_464 ?
O1 Ce1 O2 81.47(13) 5 8_666 ?
O1 Ce1 O2 63.27(11) 8_666 8_666 ?
O1 Ce1 O2 127.45(11) . 8_666 ?
O1 Ce1 O2 63.27(11) 4_464 4_464 ?
O1 Ce1 O2 81.48(13) . 4_464 ?
O1 Ce1 O3 73.14(12) 5 5 ?
O1 Ce1 O3 80.31(14) 4_464 . ?
O1 Ce1 O3 73.14(12) . . ?
O1 Ce1 O3 80.31(14) 8_666 5 ?
O1 Ce1 O3 80.35(15) . 5 ?
O1 Ce1 O3 137.33(12) 4_464 5 ?
O1 Ce1 O3 80.35(15) 5 . ?
O1 Ce1 O3 137.33(12) 8_666 . ?
O2 Ce1 Ce1 95.02(7) 8_666 3_655 ?
O2 Ce1 Ce1 91.29(7) 8_666 4_464 ?
O2 Ce1 Ce1 91.29(7) 4_464 3_655 ?
O2 Ce1 Ce1 95.02(7) 4_464 4_464 ?
O2 Ce1 O2 92.6(2) 8_666 4_464 ?
O2 Ce1 O3 90.81(17) 4_464 . ?
O2 Ce1 O3 90.81(17) 8_666 5 ?
O2 Ce1 O3 159.40(11) 4_464 5 ?
O2 Ce1 O3 159.40(11) 8_666 . ?
O3 Ce1 Ce1 68.17(8) 5 3_655 ?
O3 Ce1 Ce1 68.17(8) . 4_464 ?
O3 Ce1 Ce1 105.21(8) 5 4_464 ?
O3 Ce1 Ce1 105.21(8) . 3_655 ?
O3 Ce1 O3 93.1(3) 5 . ?
Ce1 O1 Ce1 112.88(14) . 3_655 ?
N1 O1 Ce1 117.0(3) . 3_655 ?
N1 O1 Ce1 123.8(3) . . ?
O1 N1 H1 120.5 . . ?
C1 N1 O1 119.0(4) . . ?
C1 N1 H1 120.5 . . ?
C1 O2 Ce1 119.3(3) . 3_655 ?
C5 O3 Ce1 137.5(5) . . ?
N1 C1 C2 117.7(5) . . ?
O2 C1 N1 120.5(5) . . ?
O2 C1 C2 121.7(6) . . ?
C3 C2 C1 117.8(6) . . ?
C4 C2 C1 124.4(6) . . ?
C4 C2 C3 117.0(6) . . ?
C2 C3 C3 121.8(4) . 10_564 ?
C2 C3 H3 119.1 . . ?
C3 C3 H3 119.1 10_564 . ?
O3 C5 O3 128.6(8) 7_455 . ?
O3 C5 C6 114.4(9) . 7_455 ?
O3 C5 C6 114.4(9) 7_455 . ?
O3 C5 C6 113.9(9) 7_455 7_455 ?
O3 C5 C6 113.9(9) . . ?
C6 C5 C6 38.7(17) . 7_455 ?
C2 C4 C4 118.8(6) . 10_564 ?
C2 C4 H4 120.6 . . ?
C4 C4 H4 120.6 10_564 . ?
C5 C6 H6A 109(4) . 7_455 ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6A 77.9 . 7_455 ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6A 34.4 . 7_455 ?
H6B C6 H6C 109.5 . . ?
H6C C6 H6A 135.0 . 7_455 ?

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 N1 C1 158.3(5) . . . . ?
Ce1 O1 N1 C1 8.3(8) 3_655 . . . ?
Ce1 O2 C1 N1 -5.8(10) 3_655 . . . ?
Ce1 O2 C1 C2 177.3(6) 3_655 . . . ?
Ce1 O3 C5 O3 0.4(4) . . . 7_455 ?
Ce1 O3 C5 C6 159.0(10) . . . 7_455 ?
Ce1 O3 C5 C6 -158.4(10) . . . . ?
O1 N1 C1 O2 -1.8(11) . . . . ?
O1 N1 C1 C2 175.2(7) . . . . ?
N1 C1 C2 C3 -174.1(8) . . . . ?
N1 C1 C2 C4 16.9(15) . . . . ?
O2 C1 C2 C3 2.9(12) . . . . ?
O2 C1 C2 C4 -166.1(11) . . . . ?
C1 C2 C3 C3 -178.1(8) . . . 10_564 ?
C1 C2 C4 C4 -170.8(14) . . . 10_564 ?
C3 C2 C4 C4 20(2) . . . 10_564 ?
C4 C2 C3 C3 -8.3(16) . . . 10_564 ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.250 0.250 -0.866 1441.0 481.9 ?
2 -0.250 0.750 -0.365 1441.0 481.9 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.50(2)
2 0.50(2)

