# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1874854'
_audit_update_record             
;
2018-10-23 deposited with the CCDC.
2019-01-04 downloaded from the CCDC.
;
#===================================================================== 

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C56 H42 Gd3 N8 O39'
_chemical_formula_sum            'C56 H42 Gd3 N8 O39'
_chemical_formula_weight         1922.72

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'
Gd Gd -0.1653 3.9035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      cubic
_space_group_IT_number           220
_space_group_name_H-M_alt        'I -4 3 d'
_space_group_name_Hall           'I -4bd 2c 3'

_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'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'z, x, y'
'z+1/2, -x+1/2, -y'
'-z+1/2, -x, y+1/2'
'-z, x+1/2, -y+1/2'
'y, z, x'
'-y, z+1/2, -x+1/2'
'y+1/2, -z+1/2, -x'
'-y+1/2, -z, x+1/2'
'y+1/4, x+1/4, z+1/4'
'-y+1/4, -x+3/4, z+3/4'
'y+3/4, -x+1/4, -z+3/4'
'-y+3/4, x+3/4, -z+1/4'
'x+1/4, z+1/4, y+1/4'
'-x+3/4, z+3/4, -y+1/4'
'-x+1/4, -z+3/4, y+3/4'
'x+3/4, -z+1/4, -y+3/4'
'z+1/4, y+1/4, x+1/4'
'z+3/4, -y+1/4, -x+3/4'
'-z+3/4, y+3/4, -x+1/4'
'-z+1/4, -y+3/4, x+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-x+1/2, y+1, -z+1'
'x+1, -y+1, -z+1/2'
'z+1/2, x+1/2, y+1/2'
'z+1, -x+1, -y+1/2'
'-z+1, -x+1/2, y+1'
'-z+1/2, x+1, -y+1'
'y+1/2, z+1/2, x+1/2'
'-y+1/2, z+1, -x+1'
'y+1, -z+1, -x+1/2'
'-y+1, -z+1/2, x+1'
'y+3/4, x+3/4, z+3/4'
'-y+3/4, -x+5/4, z+5/4'
'y+5/4, -x+3/4, -z+5/4'
'-y+5/4, x+5/4, -z+3/4'
'x+3/4, z+3/4, y+3/4'
'-x+5/4, z+5/4, -y+3/4'
'-x+3/4, -z+5/4, y+5/4'
'x+5/4, -z+3/4, -y+5/4'
'z+3/4, y+3/4, x+3/4'
'z+5/4, -y+3/4, -x+5/4'
'-z+5/4, y+5/4, -x+3/4'
'-z+3/4, -y+5/4, x+5/4'

_cell_length_a                   24.9640(3)
_cell_length_b                   24.9640(3)
_cell_length_c                   24.9640(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     15557.6(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9963
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      26.29

_exptl_crystal_description       prismatic
_exptl_crystal_colour            'Bright yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_F_000             7504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.057
_exptl_crystal_size_mid          0.031
_exptl_crystal_size_min          0.025
_exptl_absorpt_coefficient_mu    2.622
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            129624
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.580
_diffrn_reflns_theta_max         26.347
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2643
_reflns_number_gt                2595
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.868
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0544P)²+27.2780P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1184 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2643
_refine_ls_number_parameters     175
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0231
_refine_ls_R_factor_gt           0.0226
_refine_ls_wR_factor_ref         0.0671
_refine_ls_wR_factor_gt          0.0666
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.000
_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
Gd1 Gd 0.5000 -0.7500 0.03779(2) 0.01374(12) Uani 1 2 d S T P . .
O1W O 0.3190(10) -0.7726(12) 0.0345(11) 0.072(8) Uani 0.25 1 d . U P . .
O2W O 0.2500 -0.606(2) 0.0000 0.12(2) Uani 0.25 2 d S T P . .
O3W O 0.2500 -0.8423(15) 0.0000 0.058(8) Uani 0.25 2 d S T P . .
C11 C 0.3954(3) -0.6322(2) 0.1213(3) 0.0310(14) Uani 1 1 d . . . . .
O11 O 0.42359(15) -0.70035(16) 0.18085(16) 0.0232(8) Uani 1 1 d . . . . .
N11 N 0.4036(3) -0.5228(3) 0.0196(3) 0.0535(18) Uani 1 1 d . . . . .
C12 C 0.3568(3) -0.6122(3) 0.1558(2) 0.0275(13) Uani 1 1 d . . . . .
H12A H 0.3462 -0.6322 0.1864 0.033 Uiso 1 1 calc R U . . .
O12 O 0.43754(16) -0.71189(17) 0.09295(16) 0.0258(8) Uani 1 1 d . . . . .
C13 C 0.3333(3) -0.5618(3) 0.1451(2) 0.0305(12) Uani 1 1 d . . . . .
O13 O 0.27814(16) -0.56664(16) 0.22351(16) 0.0255(8) Uani 1 1 d . . . . .
C14 C 0.3489(3) -0.5332(3) 0.1003(3) 0.0351(14) Uani 1 1 d . . . . .
H14A H 0.3334 -0.4992 0.0928 0.042 Uiso 1 1 calc R U . . .
O14 O 0.27115(18) -0.4953(2) 0.17130(18) 0.0340(9) Uani 1 1 d . . . . .
C15 C 0.3871(3) -0.5547(3) 0.0667(3) 0.0371(14) Uani 1 1 d . . . . .
O15 O 0.3859(4) -0.4782(3) 0.0155(3) 0.094(3) Uani 1 1 d . . . . .
C16 C 0.4107(3) -0.6037(3) 0.0754(3) 0.0353(14) Uani 1 1 d . . . . .
H16A H 0.4364 -0.6178 0.0511 0.042 Uiso 1 1 calc R U . . .
O16 O 0.4346(3) -0.5438(3) -0.0123(2) 0.0648(18) Uani 1 1 d . . . . .
C17 C 0.4200(2) -0.6867(2) 0.1325(2) 0.0253(12) Uani 1 1 d . . . . .
C18 C 0.2914(2) -0.5407(2) 0.1818(2) 0.0248(11) Uani 1 1 d . . . . .
C21 C 0.3759(3) -0.9396(3) -0.1340(4) 0.054(2) Uani 1 1 d . . . . .
H21A H 0.3535 -0.9164 -0.1563 0.080 Uiso 1 1 calc R U . . .
H21B H 0.4015 -0.9588 -0.1567 0.080 Uiso 1 1 calc R U . . .
H21C H 0.3533 -0.9654 -0.1150 0.080 Uiso 1 1 calc R U . . .
N21 N 0.4060(3) -0.9060(3) -0.0940(3) 0.041(2) Uani 1 3 d S T P . .
C22 C 0.4404(4) -0.9404(4) -0.0596(4) 0.087(6) Uani 1 3 d S T P . .
H22A H 0.4180 -0.9662 -0.0403 0.131 Uiso 0.3333 1 calc R U P . .
H22B H 0.4662 -0.9597 -0.0820 0.131 Uiso 0.3333 1 calc R U P . .
H22C H 0.4597 -0.9180 -0.0338 0.131 Uiso 0.3333 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
Gd1 O12 2.288(4) . ?
Gd1 O12 2.288(4) 26_534 ?
Gd1 O11 2.406(4) 39_544 ?
Gd1 O11 2.406(4) 16_435 ?
Gd1 O13 2.432(4) 23_545 ?
Gd1 O13 2.432(4) 46_434 ?
Gd1 O14 2.457(4) 46_434 ?
Gd1 O14 2.457(4) 23_545 ?
Gd1 C18 2.800(6) 46_434 ?
Gd1 C18 2.800(6) 23_545 ?
O2W O2W 0.96(11) 46_434 ?
C11 C12 1.386(9) . ?
C11 C16 1.401(9) . ?
C11 C17 1.518(8) . ?
O11 C17 1.259(7) . ?
O11 Gd1 2.406(4) 39_544 ?
N11 O15 1.203(9) . ?
N11 O16 1.227(9) . ?
N11 C15 1.478(9) . ?
C12 C13 1.414(9) . ?
C12 H12A 0.9500 . ?
O12 C17 1.249(7) . ?
C13 C14 1.383(9) . ?
C13 C18 1.486(8) . ?
O13 C18 1.270(7) . ?
O13 Gd1 2.432(4) 47_445 ?
C14 C15 1.380(9) . ?
C14 H14A 0.9500 . ?
O14 C18 1.270(8) . ?
O14 Gd1 2.457(4) 47_445 ?
C15 C16 1.376(10) . ?
C16 H16A 0.9500 . ?
C18 Gd1 2.800(6) 47_445 ?
C21 N21 1.503(9) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
N21 C22 1.49(2) . ?
N21 C21 1.503(9) 12_444 ?
N21 C21 1.503(9) 6_544 ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O12 Gd1 O12 106.0(2) . 26_534 ?
O12 Gd1 O11 79.95(15) . 39_544 ?
O12 Gd1 O11 77.45(15) 26_534 39_544 ?
O12 Gd1 O11 77.45(15) . 16_435 ?
O12 Gd1 O11 79.95(15) 26_534 16_435 ?
O11 Gd1 O11 142.02(18) 39_544 16_435 ?
O12 Gd1 O13 151.32(14) . 23_545 ?
O12 Gd1 O13 86.42(14) 26_534 23_545 ?
O11 Gd1 O13 128.50(13) 39_544 23_545 ?
O11 Gd1 O13 79.51(13) 16_435 23_545 ?
O12 Gd1 O13 86.42(14) . 46_434 ?
O12 Gd1 O13 151.32(14) 26_534 46_434 ?
O11 Gd1 O13 79.51(13) 39_544 46_434 ?
O11 Gd1 O13 128.50(13) 16_435 46_434 ?
O13 Gd1 O13 94.8(2) 23_545 46_434 ?
O12 Gd1 O14 80.53(16) . 46_434 ?
O12 Gd1 O14 152.31(16) 26_534 46_434 ?
O11 Gd1 O14 130.15(15) 39_544 46_434 ?
O11 Gd1 O14 75.22(14) 16_435 46_434 ?
O13 Gd1 O14 77.26(15) 23_545 46_434 ?
O13 Gd1 O14 53.86(13) 46_434 46_434 ?
O12 Gd1 O14 152.31(16) . 23_545 ?
O12 Gd1 O14 80.53(16) 26_534 23_545 ?
O11 Gd1 O14 75.22(14) 39_544 23_545 ?
O11 Gd1 O14 130.15(15) 16_435 23_545 ?
O13 Gd1 O14 53.86(13) 23_545 23_545 ?
O13 Gd1 O14 77.26(15) 46_434 23_545 ?
O14 Gd1 O14 106.4(2) 46_434 23_545 ?
O12 Gd1 C18 81.96(16) . 46_434 ?
O12 Gd1 C18 172.06(15) 26_534 46_434 ?
O11 Gd1 C18 104.79(16) 39_544 46_434 ?
O11 Gd1 C18 101.80(17) 16_435 46_434 ?
O13 Gd1 C18 86.30(16) 23_545 46_434 ?
O13 Gd1 C18 26.92(16) 46_434 46_434 ?
O14 Gd1 C18 26.95(17) 46_434 46_434 ?
O14 Gd1 C18 92.61(17) 23_545 46_434 ?
O12 Gd1 C18 172.06(16) . 23_545 ?
O12 Gd1 C18 81.96(16) 26_534 23_545 ?
O11 Gd1 C18 101.80(17) 39_544 23_545 ?
O11 Gd1 C18 104.79(16) 16_435 23_545 ?
O13 Gd1 C18 26.92(16) 23_545 23_545 ?
O13 Gd1 C18 86.30(16) 46_434 23_545 ?
O14 Gd1 C18 92.61(17) 46_434 23_545 ?
O14 Gd1 C18 26.95(17) 23_545 23_545 ?
C18 Gd1 C18 90.1(2) 46_434 23_545 ?
C12 C11 C16 121.1(6) . . ?
C12 C11 C17 119.3(5) . . ?
C16 C11 C17 119.6(6) . . ?
C17 O11 Gd1 120.5(3) . 39_544 ?
O15 N11 O16 124.9(7) . . ?
O15 N11 C15 117.6(7) . . ?
O16 N11 C15 117.5(6) . . ?
C11 C12 C13 119.4(5) . . ?
C11 C12 H12A 120.3 . . ?
C13 C12 H12A 120.3 . . ?
C17 O12 Gd1 157.4(4) . . ?
C14 C13 C12 119.7(6) . . ?
C14 C13 C18 120.9(6) . . ?
C12 C13 C18 119.4(5) . . ?
C18 O13 Gd1 92.9(3) . 47_445 ?
C15 C14 C13 119.1(6) . . ?
C15 C14 H14A 120.5 . . ?
C13 C14 H14A 120.5 . . ?
C18 O14 Gd1 91.7(3) . 47_445 ?
C16 C15 C14 123.1(6) . . ?
C16 C15 N11 119.0(6) . . ?
C14 C15 N11 117.9(6) . . ?
C15 C16 C11 117.6(6) . . ?
C15 C16 H16A 121.2 . . ?
C11 C16 H16A 121.2 . . ?
O12 C17 O11 126.6(5) . . ?
O12 C17 C11 116.6(5) . . ?
O11 C17 C11 116.6(5) . . ?
O13 C18 O14 121.4(5) . . ?
O13 C18 C13 120.6(5) . . ?
O14 C18 C13 118.0(5) . . ?
O13 C18 Gd1 60.1(3) . 47_445 ?
O14 C18 Gd1 61.3(3) . 47_445 ?
C13 C18 Gd1 179.3(5) . 47_445 ?
N21 C21 H21A 109.5 . . ?
N21 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N21 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C22 N21 C21 110.4(6) . 12_444 ?
C22 N21 C21 110.4(6) . 6_544 ?
C21 N21 C21 108.5(6) 12_444 6_544 ?
C22 N21 C21 110.4(6) . . ?
C21 N21 C21 108.5(6) 12_444 . ?
C21 N21 C21 108.5(6) 6_544 . ?
N21 C22 H22A 109.5 . . ?
N21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_refine_diff_density_max         0.726
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.113



_chemical_properties_physical    Light-sensitive
_exptl_crystal_preparation       'Proton conduction'
