# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# 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. 
# 
#######################################################################

data_TN1-Eu
_database_code_depnum_ccdc_archive 'CCDC 1946819'
loop_
_audit_author_name
_audit_author_address
'Andrzej Gladysiak'
;Ecole polytechnique federale de Lausanne
Switzerland
;
_audit_update_record             
;
2019-08-13 deposited with the CCDC.	2020-05-04 downloaded from the CCDC.
;
_audit_creation_date             2019-08-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C66 H72 B2 Eu2 O12)'
_chemical_formula_sum            'C33 H36 B Eu O6'
_chemical_formula_weight         691.37
_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'
B B 0.0013 0.0007 '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'
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      trigonal
_space_group_IT_number           163
_space_group_name_H-M_alt        'P -3 1 c'
_space_group_name_Hall           '-P 3 2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, -z+1/2'
'-x+y, y, -z+1/2'
'x, x-y, -z+1/2'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'y, x, z-1/2'
'x-y, -y, z-1/2'
'-x, -x+y, z-1/2'

_cell_length_a                   14.5046(9)
_cell_length_b                   14.5046(9)
_cell_length_c                   9.2626(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1687.6(2)
_cell_formula_units_Z            2.00004
_cell_measurement_reflns_used    3206
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      24.629
_cell_measurement_theta_min      2.732
_shelx_estimated_absorpt_T_max   0.954
_shelx_estimated_absorpt_T_min   0.895
_exptl_absorpt_coefficient_mu    1.897
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6546
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0834 before and 0.0681 after correction. The Ratio of minimum to maximum transmission is 0.8784. 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    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             700
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.025
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1077
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12798
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.022
_diffrn_reflns_theta_max         25.022
_diffrn_reflns_theta_min         2.732
_diffrn_ambient_temperature      99.95
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                728
_reflns_number_total             1005
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         1.107
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.117
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     67
_refine_ls_number_reflns         1005
_refine_ls_number_restraints     66
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.025
_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)+(0.0693P)²+1.4606P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1108
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained planarity
 C2, C3_$1, C3, C4_$1, C4, C5
 with sigma of 0.0005
3. Uiso/Uaniso restraints and constraints
Uanis(C5) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C2) \\sim
Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.005
4. Rigid body (RIGU) restrains
 C1, C2, C3, C4, C5, C6, C7
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Idealised Me refined as rotating group:
 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
B1 B 0.6667 0.3333 0.2500 0.022(3) Uani 1 6 d S T P . .
C1 C 0.9011(3) 0.8021(6) 0.2500 0.0196(16) Uani 1 2 d S TU P . .
C2 C 0.8407(3) 0.6815(6) 0.2500 0.0178(15) Uani 1 2 d S TU P . .
C3 C 0.7534(3) 0.6280(4) 0.3427(5) 0.0217(12) Uani 1 1 d . U . . .
C4 C 0.6982(3) 0.5163(4) 0.3417(4) 0.0214(12) Uani 1 1 d . U . . .
C5 C 0.7298(3) 0.4596(6) 0.2500 0.0181(15) Uani 1 2 d S TU P . .
C6 C 0.7121(5) 0.6872(5) 0.4300(8) 0.0350(16) Uani 1 1 d . U . . .
H6A H 0.7340 0.6909 0.5310 0.053 Uiso 1 1 calc GR . . . .
H6B H 0.6342 0.6498 0.4244 0.053 Uiso 1 1 calc GR . . . .
H6C H 0.7411 0.7594 0.3916 0.053 Uiso 1 1 calc GR . . . .
C7 C 0.6133(5) 0.4605(5) 0.4550(7) 0.0366(16) Uani 1 1 d . U . . .
H7A H 0.5457 0.4518 0.4198 0.055 Uiso 1 1 calc GR . . . .
H7B H 0.6342 0.5032 0.5437 0.055 Uiso 1 1 calc GR . . . .
H7C H 0.6050 0.3905 0.4753 0.055 Uiso 1 1 calc GR . . . .
Eu1 Eu 1.0000 1.0000 0.5000 0.0190(3) Uani 1 6 d S T P . .
O1 O 0.9428(3) 0.8491(3) 0.3661(4) 0.0273(9) 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
B1 C5 1.586(7) 3_665 ?
B1 C5 1.586(7) . ?
B1 C5 1.586(7) 2_655 ?
C1 C2 1.516(10) . ?
C1 O1 1.255(5) 5_655 ?
C1 O1 1.255(5) . ?
C2 C3 1.400(6) 5_655 ?
C2 C3 1.400(6) . ?
C3 C4 1.404(7) . ?
C3 C6 1.505(7) . ?
C4 C5 1.409(6) . ?
C4 C7 1.508(7) . ?
C5 C4 1.409(6) 5_655 ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
Eu1 O1 2.280(4) 7_776 ?
Eu1 O1 2.281(4) 9_656 ?
Eu1 O1 2.281(4) . ?
Eu1 O1 2.280(4) 8_566 ?
Eu1 O1 2.281(4) 3_675 ?
Eu1 O1 2.280(4) 2_765 ?

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
C5 B1 C5 120.0 3_665 2_655 ?
C5 B1 C5 120.0 2_655 . ?
C5 B1 C5 120.000(1) 3_665 . ?
O1 C1 C2 118.0(3) 5_655 . ?
O1 C1 C2 118.0(3) . . ?
O1 C1 O1 123.9(7) . 5_655 ?
C3 C2 C1 118.6(3) . . ?
C3 C2 C1 118.6(3) 5_655 . ?
C3 C2 C3 122.7(7) 5_655 . ?
C2 C3 C4 118.1(5) . . ?
C2 C3 C6 121.5(5) . . ?
C4 C3 C6 120.1(5) . . ?
C3 C4 C5 120.9(5) . . ?
C3 C4 C7 117.1(4) . . ?
C5 C4 C7 121.6(5) . . ?
C4 C5 B1 120.4(3) 5_655 . ?
C4 C5 B1 120.4(3) . . ?
C4 C5 C4 119.3(6) . 5_655 ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 Eu1 O1 86.75(13) 2_765 9_656 ?
O1 Eu1 O1 93.25(13) 2_765 . ?
O1 Eu1 O1 93.25(13) 8_566 9_656 ?
O1 Eu1 O1 86.75(13) 7_776 3_675 ?
O1 Eu1 O1 93.25(13) 7_776 9_656 ?
O1 Eu1 O1 93.25(13) 2_765 3_675 ?
O1 Eu1 O1 180.0 9_656 3_675 ?
O1 Eu1 O1 86.75(13) . 9_656 ?
O1 Eu1 O1 93.25(14) 7_776 8_566 ?
O1 Eu1 O1 86.75(13) 8_566 3_675 ?
O1 Eu1 O1 86.75(14) 7_776 2_765 ?
O1 Eu1 O1 93.25(14) . 3_675 ?
O1 Eu1 O1 180.0 8_566 2_765 ?
O1 Eu1 O1 180.0 7_776 . ?
O1 Eu1 O1 86.75(14) 8_566 . ?
C1 O1 Eu1 146.3(4) . . ?

_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 0.333 0.667 0.250 169.6 26.8 ?
2 -0.333 0.333 0.750 169.6 26.8 ?


_olex2_submission_original_sample_id TN2_107a
_olex2_submission_special_instructions 'No special instructions were received'
