# Electronic Supplementary Material (ESI) for Molecular Systems Design & Engineering.
# 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_shelx
_audit_block_doi                 10.5517/ccdc.csd.cc245ctj
_database_code_depnum_ccdc_archive 'CCDC 1971377'
loop_
_audit_author_name
_audit_author_address
'Nikos Panagiotou'
;University of Cyprus
Cyprus
;
_audit_update_record             
;
2019-12-11 deposited with the CCDC.	2020-05-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C42 H24 Ho3 O19, 3(C2 H8 N) [+ solvent]'
_chemical_formula_sum            'C48 H48 Ho3 N3 O22'
_chemical_formula_weight         1513.68

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'
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'
Ho Ho -14.9734 3.7046 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 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'
'-y, x-y, z'
'-x+y, -x, 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+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, -z'
'y, -x+y, -z'
'x-y, x, -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+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'

_cell_length_a                   27.7647(11)
_cell_length_b                   27.7647(11)
_cell_length_c                   24.6333(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     16445.2(16)
_cell_formula_units_Z            6
_cell_measurement_temperature    109(7)
_cell_measurement_reflns_used    7194
_cell_measurement_theta_min      5.1180
_cell_measurement_theta_max      71.9730

_exptl_crystal_description       plate
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.917
_exptl_crystal_F_000             4404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.046
_exptl_crystal_size_mid          0.044
_exptl_crystal_size_min          0.026
_exptl_absorpt_coefficient_mu    4.220
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.83052
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.691
_oxdiff_exptl_absorpt_empirical_full_max 1.478
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      109(7)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4223
_diffrn_reflns_number            30299
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         4.033
_diffrn_reflns_theta_max         67.000
_diffrn_reflns_theta_full        67.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6540
_reflns_number_gt                4918
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1312P)²+11.1592P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6540
_refine_ls_number_parameters     222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0602
_refine_ls_wR_factor_ref         0.1934
_refine_ls_wR_factor_gt          0.1838
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.002
_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 0.4406(2) 0.6885(2) 0.3207(2) 0.0648(13) Uani 1 1 d . . . . .
C2 C 0.4778(2) 0.6966(2) 0.3680(2) 0.0657(13) Uani 1 1 d . . . . .
C3 C 0.4731(3) 0.6508(3) 0.3959(3) 0.095(2) Uani 1 1 d . . . . .
H3 H 0.447181 0.614869 0.385078 0.114 Uiso 1 1 calc R U . . .
C4 C 0.5180(2) 0.7488(3) 0.3821(3) 0.0772(15) Uani 1 1 d . . . . .
H4 H 0.522260 0.779010 0.361878 0.093 Uiso 1 1 calc R U . . .
C5 C 0.5078(3) 0.6596(3) 0.4401(3) 0.109(3) Uani 1 1 d . . . . .
H5 H 0.504400 0.629466 0.459745 0.131 Uiso 1 1 calc R U . . .
C6 C 0.5538(2) 0.7580(3) 0.4275(3) 0.0853(19) Uani 1 1 d . . . . .
H6 H 0.580625 0.793780 0.437625 0.102 Uiso 1 1 calc R U . . .
C7 C 0.5474(2) 0.7134(3) 0.4549(3) 0.090(2) Uani 1 1 d . . . . .
C8 C 0.6359(2) 0.7573(3) 0.4976(3) 0.090(2) Uani 1 1 d . . . . .
C9 C 0.6677(3) 0.7597(3) 0.4540(3) 0.091(2) Uani 1 1 d . . . . .
H9 H 0.651572 0.736298 0.424365 0.110 Uiso 1 1 calc R U . . .
C10 C 0.6585(2) 0.7921(3) 0.5438(3) 0.099(2) Uani 1 1 d . . . . .
H10 H 0.636417 0.791014 0.572696 0.119 Uiso 1 1 calc R U . . .
C11 C 0.7246(2) 0.7979(3) 0.4547(3) 0.0780(16) Uani 1 1 d . . . . .
H11 H 0.746878 0.800820 0.425270 0.094 Uiso 1 1 calc R U . . .
C12 C 0.7155(2) 0.8277(3) 0.5431(3) 0.0830(18) Uani 1 1 d . . . . .
H12 H 0.732455 0.849841 0.573390 0.100 Uiso 1 1 calc R U . . .
C13 C 0.74766(19) 0.8315(2) 0.5000(2) 0.0629(12) Uani 1 1 d . . . . .
C14 C 0.80959(19) 0.8727(2) 0.5006(2) 0.0591(12) Uani 1 1 d . . . . .
C15 C 0.4363(4) 0.4600(4) 0.0432(5) 0.131(3) Uani 1 1 d . . . . .
H15A H 0.457981 0.497705 0.030868 0.197 Uiso 1 1 calc R U . . .
H15B H 0.436070 0.435283 0.015778 0.197 Uiso 1 1 calc R U . . .
H15C H 0.452349 0.455315 0.075927 0.197 Uiso 1 1 calc R U . . .
C16 C 0.3779(3) 0.4920(3) 0.0863(3) 0.0810(16) Uani 1 1 d . . . . .
H16A H 0.385709 0.488934 0.123717 0.121 Uiso 1 1 calc R U . . .
H16B H 0.341331 0.487255 0.083229 0.121 Uiso 1 1 calc R U . . .
H16C H 0.404799 0.527939 0.072724 0.121 Uiso 1 1 calc R U . . .
N1 N 0.3809(6) 0.4475(5) 0.0537(7) 0.338(12) Uani 1 1 d . . . . .
H1A H 0.363052 0.415436 0.071549 0.406 Uiso 1 1 calc R U . . .
H1B H 0.363445 0.443274 0.022190 0.406 Uiso 1 1 calc R U . . .
O1 O 0.333333 0.666667 0.2546(2) 0.0445(10) Uani 1 3 d S T P . .
O2 O 0.26942(11) 0.58652(12) 0.19597(13) 0.0470(6) Uani 1 1 d . . . . .
O3 O 0.40993(14) 0.63846(16) 0.30398(15) 0.0666(9) Uani 1 1 d . . . . .
O4 O 0.44176(14) 0.73127(16) 0.30173(15) 0.0653(9) Uani 1 1 d . . . . .
O5 O 0.57866(17) 0.7176(2) 0.49999(19) 0.113(2) Uani 1 1 d . . . . .
O6 O 0.30341(15) 0.50503(14) 0.20385(16) 0.0664(9) Uani 1 1 d . . . . .
O7 O 0.42551(14) 0.58635(15) 0.20555(15) 0.0632(8) Uani 1 1 d . . . . .
Ho01 Ho 0.35098(2) 0.59651(2) 0.23110(2) 0.05617(18) 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
C1 O4 1.260(7) . ?
C1 O3 1.281(7) . ?
C1 C2 1.499(7) . ?
C2 C4 1.358(8) . ?
C2 C3 1.394(9) . ?
C3 C5 1.392(9) . ?
C3 H3 0.9300 . ?
C4 C6 1.432(8) . ?
C4 H4 0.9300 . ?
C5 C7 1.390(10) . ?
C5 H5 0.9300 . ?
C6 C7 1.343(9) . ?
C6 H6 0.9300 . ?
C7 O5 1.378(7) . ?
C8 C9 1.371(10) . ?
C8 O5 1.411(6) . ?
C8 C10 1.419(10) . ?
C9 C11 1.396(8) . ?
C9 H9 0.9300 . ?
C10 C12 1.386(8) . ?
C10 H10 0.9300 . ?
C11 C13 1.386(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.358(9) . ?
C12 H12 0.9300 . ?
C13 C14 1.516(6) . ?
C14 O7 1.265(6) 6_565 ?
C14 O6 1.273(6) 17 ?
C15 N1 1.423(14) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 N1 1.508(13) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
O1 Ho01 2.3073(13) . ?
O1 Ho01 2.3074(13) 2_665 ?
O1 Ho01 2.3075(13) 3_565 ?
O2 Ho01 2.308(3) . ?
O2 Ho01 2.313(3) 3_565 ?
O2 Ho01 2.317(3) 14_455 ?
O3 Ho01 2.313(4) . ?
O4 Ho01 2.293(4) 2_665 ?
O6 Ho01 2.300(3) . ?
O7 Ho01 2.311(3) . ?
Ho01 Ho01 3.8685(6) 2_665 ?
Ho01 Ho01 3.8686(6) 3_565 ?
Ho01 Ho01 3.8814(7) 15 ?
Ho01 Ho01 3.8815(7) 14_455 ?

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
O4 C1 O3 126.4(5) . . ?
O4 C1 C2 117.0(5) . . ?
O3 C1 C2 116.5(5) . . ?
C4 C2 C3 120.0(5) . . ?
C4 C2 C1 119.7(5) . . ?
C3 C2 C1 120.2(5) . . ?
C2 C3 C5 118.9(6) . . ?
C2 C3 H3 120.5 . . ?
C5 C3 H3 120.5 . . ?
C2 C4 C6 121.0(6) . . ?
C2 C4 H4 119.5 . . ?
C6 C4 H4 119.5 . . ?
C7 C5 C3 120.1(6) . . ?
C7 C5 H5 120.0 . . ?
C3 C5 H5 120.0 . . ?
C7 C6 C4 118.0(6) . . ?
C7 C6 H6 121.0 . . ?
C4 C6 H6 121.0 . . ?
C6 C7 O5 122.8(6) . . ?
C6 C7 C5 121.8(6) . . ?
O5 C7 C5 115.4(6) . . ?
C9 C8 O5 121.1(6) . . ?
C9 C8 C10 122.6(5) . . ?
O5 C8 C10 116.2(6) . . ?
C8 C9 C11 119.0(6) . . ?
C8 C9 H9 120.5 . . ?
C11 C9 H9 120.5 . . ?
C12 C10 C8 115.8(6) . . ?
C12 C10 H10 122.1 . . ?
C8 C10 H10 122.1 . . ?
C13 C11 C9 119.2(6) . . ?
C13 C11 H11 120.4 . . ?
C9 C11 H11 120.4 . . ?
C13 C12 C10 122.4(6) . . ?
C13 C12 H12 118.8 . . ?
C10 C12 H12 118.8 . . ?
C12 C13 C11 120.9(5) . . ?
C12 C13 C14 120.2(5) . . ?
C11 C13 C14 118.9(5) . . ?
O7 C14 O6 126.6(4) 6_565 17 ?
O7 C14 C13 116.8(5) 6_565 . ?
O6 C14 C13 116.7(5) 17 . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 N1 C16 113.1(13) . . ?
C15 N1 H1A 109.0 . . ?
C16 N1 H1A 109.0 . . ?
C15 N1 H1B 109.0 . . ?
C16 N1 H1B 109.0 . . ?
H1A N1 H1B 107.8 . . ?
Ho01 O1 Ho01 113.92(10) . 2_665 ?
Ho01 O1 Ho01 113.92(10) . 3_565 ?
Ho01 O1 Ho01 113.91(10) 2_665 3_565 ?
Ho01 O2 Ho01 113.68(12) . 3_565 ?
Ho01 O2 Ho01 114.12(12) . 14_455 ?
Ho01 O2 Ho01 113.90(12) 3_565 14_455 ?
C1 O3 Ho01 135.5(3) . . ?
C1 O4 Ho01 138.4(4) . 2_665 ?
C7 O5 C8 116.6(5) . . ?
C14 O6 Ho01 137.9(3) 18_545 . ?
C14 O7 Ho01 136.4(3) 8_654 . ?
O4 Ho01 O6 80.00(13) 3_565 . ?
O4 Ho01 O2 76.73(13) 3_565 . ?
O6 Ho01 O2 76.74(12) . . ?
O4 Ho01 O1 77.15(13) 3_565 . ?
O6 Ho01 O1 139.32(10) . . ?
O2 Ho01 O1 65.54(10) . . ?
O4 Ho01 O7 130.89(13) 3_565 . ?
O6 Ho01 O7 80.83(13) . . ?
O2 Ho01 O7 140.16(12) . . ?
O1 Ho01 O7 138.80(9) . . ?
O4 Ho01 O2 139.75(11) 3_565 2_665 ?
O6 Ho01 O2 138.99(12) . 2_665 ?
O2 Ho01 O2 99.60(14) . 2_665 ?
O1 Ho01 O2 65.45(10) . 2_665 ?
O7 Ho01 O2 76.78(11) . 2_665 ?
O4 Ho01 O3 79.62(14) 3_565 . ?
O6 Ho01 O3 130.80(14) . . ?
O2 Ho01 O3 139.14(12) . . ?
O1 Ho01 O3 77.03(13) . . ?
O7 Ho01 O3 79.72(13) . . ?
O2 Ho01 O3 78.07(12) 2_665 . ?
O4 Ho01 O2 138.97(11) 3_565 15 ?
O6 Ho01 O2 76.70(12) . 15 ?
O2 Ho01 O2 65.35(10) . 15 ?
O1 Ho01 O2 99.69(14) . 15 ?
O7 Ho01 O2 77.73(12) . 15 ?
O2 Ho01 O2 65.27(10) 2_665 15 ?
O3 Ho01 O2 140.33(11) . 15 ?
O4 Ho01 Ho01 107.26(9) 3_565 2_665 ?
O6 Ho01 Ho01 159.16(10) . 2_665 ?
O2 Ho01 Ho01 85.83(7) . 2_665 ?
O1 Ho01 Ho01 33.04(5) . 2_665 ?
O7 Ho01 Ho01 106.59(9) . 2_665 ?
O2 Ho01 Ho01 33.12(7) 2_665 2_665 ?
O3 Ho01 Ho01 70.04(10) . 2_665 ?
O2 Ho01 Ho01 85.76(7) 15 2_665 ?
O4 Ho01 Ho01 69.29(9) 3_565 3_565 ?
O6 Ho01 Ho01 106.93(10) . 3_565 ?
O2 Ho01 Ho01 33.21(7) . 3_565 ?
O1 Ho01 Ho01 33.04(5) . 3_565 ?
O7 Ho01 Ho01 159.80(9) . 3_565 ?
O2 Ho01 Ho01 85.76(7) 2_665 3_565 ?
O3 Ho01 Ho01 106.77(10) . 3_565 ?
O2 Ho01 Ho01 85.84(7) 15 3_565 ?
Ho01 Ho01 Ho01 60.0 2_665 3_565 ?
O4 Ho01 Ho01 159.27(9) 3_565 15 ?
O6 Ho01 Ho01 106.60(10) . 15 ?
O2 Ho01 Ho01 85.58(8) . 15 ?
O1 Ho01 Ho01 85.80(10) . 15 ?
O7 Ho01 Ho01 69.83(9) . 15 ?
O2 Ho01 Ho01 33.08(8) 2_665 15 ?
O3 Ho01 Ho01 108.18(9) . 15 ?
O2 Ho01 Ho01 32.86(6) 15 15 ?
Ho01 Ho01 Ho01 60.109(6) 2_665 15 ?
Ho01 Ho01 Ho01 90.0 3_565 15 ?
O4 Ho01 Ho01 106.69(10) 3_565 14_455 ?
O6 Ho01 Ho01 69.17(10) . 14_455 ?
O2 Ho01 Ho01 33.02(8) . 14_455 ?
O1 Ho01 Ho01 85.80(10) . 14_455 ?
O7 Ho01 Ho01 107.82(9) . 14_455 ?
O2 Ho01 Ho01 85.59(8) 2_665 14_455 ?
O3 Ho01 Ho01 160.02(10) . 14_455 ?
O2 Ho01 Ho01 33.01(7) 15 14_455 ?
Ho01 Ho01 Ho01 90.0 2_665 14_455 ?
Ho01 Ho01 Ho01 60.107(6) 3_565 14_455 ?
Ho01 Ho01 Ho01 59.777(12) 15 14_455 ?

_refine_diff_density_max         1.450
_refine_diff_density_min         -0.883
_refine_diff_density_rms         0.091



