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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_R_1059_TRY1_0m
_database_code_depnum_ccdc_archive 'CCDC 1841713'
_audit_update_record             
;
2018-09-16 deposited with the CCDC.
2018-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'Sodium cerium iminodiacetato biphenyl dicarboxylate'
_chemical_name_common            
'Sodium cerium iminodiacetato biphenyl dicarboxylate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C54 H36 Ce3 N3 Na3 O28'
_chemical_formula_sum            'C54 H36 Ce3 N3 Na3 O28'
_chemical_formula_weight         1664.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -1.8482 9.6596 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.1353 0.1239 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           155
_space_group_name_H-M_alt        'R 3 2 :H'
_space_group_name_Hall           'R 3 2"'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x-y, -y, -z'
'y, x, -z'
'-x, -x+y, -z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x-y+2/3, -y+1/3, -z+1/3'
'y+2/3, x+1/3, -z+1/3'
'-x+2/3, -x+y+1/3, -z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'x-y+1/3, -y+2/3, -z+2/3'
'y+1/3, x+2/3, -z+2/3'
'-x+1/3, -x+y+2/3, -z+2/3'

_cell_length_a                   12.8523(4)
_cell_length_b                   12.8523(4)
_cell_length_c                   45.7558(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     6545.4(5)
_cell_formula_units_Z            3
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2862
_cell_measurement_theta_min      4.417
_cell_measurement_theta_max      72.254

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_F_000             2436
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.5
_exptl_absorpt_coefficient_mu    12.578
_shelx_estimated_absorpt_T_min   0.000
_shelx_estimated_absorpt_T_max   0.002
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.000
_exptl_absorpt_correction_T_max  0.002
_exptl_absorpt_process_details   SADABS,2008
_exptl_absorpt_special_details   multi-scan
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  microfocus
_diffrn_measurement_method       APEXIII
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17802
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -56
_diffrn_reflns_limit_l_max       56
_diffrn_reflns_theta_min         4.417
_diffrn_reflns_theta_max         72.254
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2862
_reflns_number_gt                2834
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_max     0.990
_reflns_Friedel_fraction_full    0.992

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

_computing_data_collection       'Bruker APEXIII'
_computing_cell_refinement       'SHELXTL Suite'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond 3.0'
_computing_publication_material  ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0560P)²+105.4796P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00024(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1194 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.007(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2862
_refine_ls_number_parameters     141
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.1200
_refine_ls_wR_factor_gt          0.1199
_refine_ls_goodness_of_fit_ref   1.193
_refine_ls_restrained_S_all      1.193
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.1251(9) 0.2586(7) 0.89409(16) 0.0147(16) Uani 1 1 d . . . . .
C2 C 1.0884(8) 0.2444(8) 0.92559(18) 0.0181(18) Uani 1 1 d . . . . .
C3 C 0.9715(9) 0.1578(9) 0.9337(2) 0.026(2) Uani 1 1 d . . . . .
H3 H 0.9162 0.1096 0.9196 0.031 Uiso 1 1 calc R U . . .
C4 C 0.9385(10) 0.1443(10) 0.9631(2) 0.034(3) Uani 1 1 d . . . . .
H4 H 0.8613 0.0856 0.9684 0.041 Uiso 1 1 calc R U . . .
C5 C 1.0176(10) 0.2159(10) 0.98440(19) 0.026(2) Uani 1 1 d . . . . .
C6 C 1.1349(10) 0.3047(11) 0.9760(2) 0.029(2) Uani 1 1 d . . . . .
H6 H 1.1893 0.3547 0.9901 0.035 Uiso 1 1 calc R U . . .
C7 C 1.1686(8) 0.3172(9) 0.94698(18) 0.0239(19) Uani 1 1 d . . . . .
H7 H 1.2461 0.3753 0.9417 0.029 Uiso 1 1 calc R U . . .
C8 C 0.8783(8) 0.1334(8) 0.82149(18) 0.0167(17) Uani 1 1 d . . . . .
C9 C 0.7732(13) 0.1505(11) 0.8264(7) 0.096(10) Uani 1 1 d . . . . .
H9A H 0.7933 0.2085 0.8420 0.115 Uiso 1 1 calc R U . . .
H9B H 0.7610 0.1852 0.8088 0.115 Uiso 1 1 calc R U . . .
Ce1 Ce 1.17776(5) 0.3333 0.8333 0.0084(3) Uani 1 2 d S T P . .
N2 N 0.6667 0.0499(9) 0.8333 0.033(3) Uani 1 2 d S T P . .
Na1 Na 1.0000 0.0000 0.85505(11) 0.0110(10) Uani 1 3 d S T P . .
Na2 Na 1.0000 0.0000 0.7647(5) 0.166(18) Uani 0.5 3 d S T P . .
O1 O 1.0489(6) 0.1903(5) 0.87511(12) 0.0157(12) Uani 1 1 d . . . . .
O2 O 1.2299(6) 0.3376(6) 0.88711(12) 0.0213(15) Uani 1 1 d . . . . .
O3 O 0.9756(5) 0.2234(7) 0.81276(14) 0.0205(12) Uani 1 1 d . . . . .
O4 O 0.8635(6) 0.0312(6) 0.82651(15) 0.0166(14) Uani 1 1 d . . . . .
O100 O 0.6667 0.3333 0.8011(17) 0.28(4) Uani 1 3 d S T P . .
O200 O 1.0000 0.0000 0.6920(17) 0.29(3) Uani 1 3 d S T 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
C1 O2 1.256(12) . ?
C1 O1 1.275(10) . ?
C1 C2 1.499(11) . ?
C1 Ce1 2.908(8) . ?
C2 C7 1.390(12) . ?
C2 C3 1.401(13) . ?
C3 C4 1.394(13) . ?
C4 C5 1.377(15) . ?
C5 C6 1.415(16) . ?
C5 C5 1.481(18) 6_767 ?
C6 C7 1.381(13) . ?
C8 O4 1.251(11) . ?
C8 O3 1.271(11) . ?
C8 C9 1.489(16) . ?
C9 N2 1.370(14) . ?
Ce1 O3 2.442(6) 16_556 ?
Ce1 O3 2.442(6) . ?
Ce1 O4 2.487(7) 17_646 ?
Ce1 O4 2.487(6) 3_765 ?
Ce1 O2 2.543(6) . ?
Ce1 O2 2.543(6) 16_556 ?
Ce1 O1 2.595(6) 16_556 ?
Ce1 O1 2.595(6) . ?
Ce1 N2 2.640(12) 3_765 ?
Ce1 C1 2.908(8) 16_556 ?
Ce1 Na1 3.8435(13) . ?
N2 C9 1.370(14) 18_656 ?
N2 Ce1 2.640(12) 2_645 ?
Na1 O4 2.376(7) . ?
Na1 O4 2.376(7) 2_645 ?
Na1 O4 2.376(7) 3_765 ?
Na1 O1 2.384(6) 2_645 ?
Na1 O1 2.384(6) 3_765 ?
Na1 O1 2.384(6) . ?
Na1 Ce1 3.8435(13) 2_645 ?
Na1 Ce1 3.8435(13) 3_765 ?
Na1 Na2 4.14(2) . ?
O4 Ce1 2.487(6) 2_645 ?

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 C1 O1 121.8(7) . . ?
O2 C1 C2 119.2(8) . . ?
O1 C1 C2 119.0(8) . . ?
O2 C1 Ce1 60.8(4) . . ?
O1 C1 Ce1 63.1(4) . . ?
C2 C1 Ce1 165.1(6) . . ?
C7 C2 C3 119.2(8) . . ?
C7 C2 C1 120.8(8) . . ?
C3 C2 C1 119.9(8) . . ?
C4 C3 C2 119.5(9) . . ?
C5 C4 C3 121.6(10) . . ?
C4 C5 C6 118.6(9) . . ?
C4 C5 C5 120.9(12) . 6_767 ?
C6 C5 C5 120.4(11) . 6_767 ?
C7 C6 C5 120.0(9) . . ?
C6 C7 C2 121.0(9) . . ?
O4 C8 O3 125.3(8) . . ?
O4 C8 C9 117.0(9) . . ?
O3 C8 C9 117.7(9) . . ?
N2 C9 C8 116.6(10) . . ?
O3 Ce1 O3 78.4(4) 16_556 . ?
O3 Ce1 O4 82.2(2) 16_556 17_646 ?
O3 Ce1 O4 147.5(2) . 17_646 ?
O3 Ce1 O4 147.5(2) 16_556 3_765 ?
O3 Ce1 O4 82.2(2) . 3_765 ?
O4 Ce1 O4 125.7(3) 17_646 3_765 ?
O3 Ce1 O2 79.2(2) 16_556 . ?
O3 Ce1 O2 125.3(2) . . ?
O4 Ce1 O2 75.3(2) 17_646 . ?
O4 Ce1 O2 91.3(2) 3_765 . ?
O3 Ce1 O2 125.3(2) 16_556 16_556 ?
O3 Ce1 O2 79.2(2) . 16_556 ?
O4 Ce1 O2 91.3(2) 17_646 16_556 ?
O4 Ce1 O2 75.3(2) 3_765 16_556 ?
O2 Ce1 O2 150.8(3) . 16_556 ?
O3 Ce1 O1 75.9(2) 16_556 16_556 ?
O3 Ce1 O1 78.7(2) . 16_556 ?
O4 Ce1 O1 71.4(2) 17_646 16_556 ?
O4 Ce1 O1 125.3(2) 3_765 16_556 ?
O2 Ce1 O1 140.6(2) . 16_556 ?
O2 Ce1 O1 50.99(19) 16_556 16_556 ?
O3 Ce1 O1 78.7(2) 16_556 . ?
O3 Ce1 O1 75.9(2) . . ?
O4 Ce1 O1 125.3(2) 17_646 . ?
O4 Ce1 O1 71.4(2) 3_765 . ?
O2 Ce1 O1 51.0(2) . . ?
O2 Ce1 O1 140.6(2) 16_556 . ?
O1 Ce1 O1 147.0(3) 16_556 . ?
O3 Ce1 N2 140.78(19) 16_556 3_765 ?
O3 Ce1 N2 140.78(18) . 3_765 ?
O4 Ce1 N2 62.84(14) 17_646 3_765 ?
O4 Ce1 N2 62.85(15) 3_765 3_765 ?
O2 Ce1 N2 75.38(16) . 3_765 ?
O2 Ce1 N2 75.39(16) 16_556 3_765 ?
O1 Ce1 N2 106.52(14) 16_556 3_765 ?
O1 Ce1 N2 106.51(14) . 3_765 ?
O3 Ce1 C1 73.9(2) 16_556 . ?
O3 Ce1 C1 100.0(2) . . ?
O4 Ce1 C1 99.4(2) 17_646 . ?
O4 Ce1 C1 84.2(2) 3_765 . ?
O2 Ce1 C1 25.5(3) . . ?
O2 Ce1 C1 159.5(2) 16_556 . ?
O1 Ce1 C1 149.4(2) 16_556 . ?
O1 Ce1 C1 26.0(2) . . ?
N2 Ce1 C1 93.9(2) 3_765 . ?
O3 Ce1 C1 100.0(2) 16_556 16_556 ?
O3 Ce1 C1 73.9(2) . 16_556 ?
O4 Ce1 C1 84.2(2) 17_646 16_556 ?
O4 Ce1 C1 99.4(2) 3_765 16_556 ?
O2 Ce1 C1 159.5(2) . 16_556 ?
O2 Ce1 C1 25.5(3) 16_556 16_556 ?
O1 Ce1 C1 26.0(2) 16_556 16_556 ?
O1 Ce1 C1 149.4(2) . 16_556 ?
N2 Ce1 C1 93.9(2) 3_765 16_556 ?
C1 Ce1 C1 172.3(4) . 16_556 ?
O3 Ce1 Na1 110.81(19) 16_556 . ?
O3 Ce1 Na1 65.62(18) . . ?
O4 Ce1 Na1 146.59(15) 17_646 . ?
O4 Ce1 Na1 36.78(15) 3_765 . ?
O2 Ce1 Na1 77.14(17) . . ?
O2 Ce1 Na1 103.96(17) 16_556 . ?
O1 Ce1 Na1 140.55(15) 16_556 . ?
O1 Ce1 Na1 37.51(14) . . ?
N2 Ce1 Na1 92.126(11) 3_765 . ?
C1 Ce1 Na1 58.29(18) . . ?
C1 Ce1 Na1 121.37(17) 16_556 . ?
C9 N2 C9 127.3(14) 18_656 . ?
C9 N2 Ce1 116.3(7) 18_656 2_645 ?
C9 N2 Ce1 116.4(7) . 2_645 ?
O4 Na1 O4 92.7(3) . 2_645 ?
O4 Na1 O4 92.7(3) . 3_765 ?
O4 Na1 O4 92.7(3) 2_645 3_765 ?
O4 Na1 O1 77.1(2) . 2_645 ?
O4 Na1 O1 82.9(2) 2_645 2_645 ?
O4 Na1 O1 168.7(3) 3_765 2_645 ?
O4 Na1 O1 168.7(3) . 3_765 ?
O4 Na1 O1 77.1(2) 2_645 3_765 ?
O4 Na1 O1 82.9(2) 3_765 3_765 ?
O1 Na1 O1 106.12(19) 2_645 3_765 ?
O4 Na1 O1 82.9(2) . . ?
O4 Na1 O1 168.7(3) 2_645 . ?
O4 Na1 O1 77.2(2) 3_765 . ?
O1 Na1 O1 106.12(19) 2_645 . ?
O1 Na1 O1 106.1(2) 3_765 . ?
O4 Na1 Ce1 38.81(16) . 2_645 ?
O4 Na1 Ce1 75.38(16) 2_645 2_645 ?
O4 Na1 Ce1 127.3(2) 3_765 2_645 ?
O1 Na1 Ce1 41.50(14) 2_645 2_645 ?
O1 Na1 Ce1 139.55(16) 3_765 2_645 ?
O1 Na1 Ce1 106.65(15) . 2_645 ?
O4 Na1 Ce1 127.3(2) . 3_765 ?
O4 Na1 Ce1 38.81(15) 2_645 3_765 ?
O4 Na1 Ce1 75.38(16) 3_765 3_765 ?
O1 Na1 Ce1 106.65(15) 2_645 3_765 ?
O1 Na1 Ce1 41.50(14) 3_765 3_765 ?
O1 Na1 Ce1 139.55(15) . 3_765 ?
Ce1 Na1 Ce1 113.57(6) 2_645 3_765 ?
O4 Na1 Ce1 75.38(16) . . ?
O4 Na1 Ce1 127.3(2) 2_645 . ?
O4 Na1 Ce1 38.81(15) 3_765 . ?
O1 Na1 Ce1 139.55(15) 2_645 . ?
O1 Na1 Ce1 106.65(15) 3_765 . ?
O1 Na1 Ce1 41.50(14) . . ?
Ce1 Na1 Ce1 113.56(6) 2_645 . ?
Ce1 Na1 Ce1 113.56(6) 3_765 . ?
O4 Na1 Na2 56.7(2) . . ?
O4 Na1 Na2 56.7(2) 2_645 . ?
O4 Na1 Na2 56.7(2) 3_765 . ?
O1 Na1 Na2 112.64(18) 2_645 . ?
O1 Na1 Na2 112.64(17) 3_765 . ?
O1 Na1 Na2 112.64(17) . . ?
Ce1 Na1 Na2 75.02(7) 2_645 . ?
Ce1 Na1 Na2 75.02(7) 3_765 . ?
Ce1 Na1 Na2 75.02(7) . . ?
C1 O1 Na1 133.3(6) . . ?
C1 O1 Ce1 90.9(5) . . ?
Na1 O1 Ce1 101.0(2) . . ?
C1 O2 Ce1 93.7(5) . . ?
C8 O3 Ce1 133.1(5) . . ?
C8 O4 Na1 122.7(6) . . ?
C8 O4 Ce1 125.7(6) . 2_645 ?
Na1 O4 Ce1 104.4(2) . 2_645 ?

_refine_diff_density_max         1.276
_refine_diff_density_min         -0.906
_refine_diff_density_rms         0.210

