# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_added_by_encifer
_database_code_depnum_ccdc_archive 'CCDC 1431184'
_audit_update_record             
;
2015-10-14 deposited with the CCDC.
2015-12-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        PCN-99
_chemical_name_common            ?
_chemical_melting_point          'not measured'
_chemical_formula_moiety         'C108 H48 In3 N12 O24'
_chemical_formula_sum            'C108 H48 In3 N12 O24'
_chemical_formula_weight         2242.04

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'
In In -0.7276 1.3100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      cubic
_space_group_IT_number           225
_space_group_name_H-M_alt        'F m -3 m'
_space_group_name_Hall           '-F 4 2 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, z'
'-x, -y, z'
'y, -x, z'
'x, -z, y'
'x, -y, -z'
'x, z, -y'
'z, y, -x'
'-x, y, -z'
'-z, y, x'
'z, x, y'
'y, z, x'
'-y, -z, x'
'z, -x, -y'
'-y, z, -x'
'-z, -x, y'
'-z, x, -y'
'y, -z, -x'
'y, x, -z'
'-y, -x, -z'
'-x, z, y'
'-x, -z, -y'
'z, -y, x'
'-z, -y, -x'
'x, y+1/2, z+1/2'
'-y, x+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'y, -x+1/2, z+1/2'
'x, -z+1/2, y+1/2'
'x, -y+1/2, -z+1/2'
'x, z+1/2, -y+1/2'
'z, y+1/2, -x+1/2'
'-x, y+1/2, -z+1/2'
'-z, y+1/2, x+1/2'
'z, x+1/2, y+1/2'
'y, z+1/2, x+1/2'
'-y, -z+1/2, x+1/2'
'z, -x+1/2, -y+1/2'
'-y, z+1/2, -x+1/2'
'-z, -x+1/2, y+1/2'
'-z, x+1/2, -y+1/2'
'y, -z+1/2, -x+1/2'
'y, x+1/2, -z+1/2'
'-y, -x+1/2, -z+1/2'
'-x, z+1/2, y+1/2'
'-x, -z+1/2, -y+1/2'
'z, -y+1/2, x+1/2'
'-z, -y+1/2, -x+1/2'
'x+1/2, y, z+1/2'
'-y+1/2, x, z+1/2'
'-x+1/2, -y, z+1/2'
'y+1/2, -x, z+1/2'
'x+1/2, -z, y+1/2'
'x+1/2, -y, -z+1/2'
'x+1/2, z, -y+1/2'
'z+1/2, y, -x+1/2'
'-x+1/2, y, -z+1/2'
'-z+1/2, y, x+1/2'
'z+1/2, x, y+1/2'
'y+1/2, z, x+1/2'
'-y+1/2, -z, x+1/2'
'z+1/2, -x, -y+1/2'
'-y+1/2, z, -x+1/2'
'-z+1/2, -x, y+1/2'
'-z+1/2, x, -y+1/2'
'y+1/2, -z, -x+1/2'
'y+1/2, x, -z+1/2'
'-y+1/2, -x, -z+1/2'
'-x+1/2, z, y+1/2'
'-x+1/2, -z, -y+1/2'
'z+1/2, -y, x+1/2'
'-z+1/2, -y, -x+1/2'
'x+1/2, y+1/2, z'
'-y+1/2, x+1/2, z'
'-x+1/2, -y+1/2, z'
'y+1/2, -x+1/2, z'
'x+1/2, -z+1/2, y'
'x+1/2, -y+1/2, -z'
'x+1/2, z+1/2, -y'
'z+1/2, y+1/2, -x'
'-x+1/2, y+1/2, -z'
'-z+1/2, y+1/2, x'
'z+1/2, x+1/2, y'
'y+1/2, z+1/2, x'
'-y+1/2, -z+1/2, x'
'z+1/2, -x+1/2, -y'
'-y+1/2, z+1/2, -x'
'-z+1/2, -x+1/2, y'
'-z+1/2, x+1/2, -y'
'y+1/2, -z+1/2, -x'
'y+1/2, x+1/2, -z'
'-y+1/2, -x+1/2, -z'
'-x+1/2, z+1/2, y'
'-x+1/2, -z+1/2, -y'
'z+1/2, -y+1/2, x'
'-z+1/2, -y+1/2, -x'
'-x, -y, -z'
'y, -x, -z'
'x, y, -z'
'-y, x, -z'
'-x, z, -y'
'-x, y, z'
'-x, -z, y'
'-z, -y, x'
'x, -y, z'
'z, -y, -x'
'-z, -x, -y'
'-y, -z, -x'
'y, z, -x'
'-z, x, y'
'y, -z, x'
'z, x, -y'
'z, -x, y'
'-y, z, x'
'-y, -x, z'
'y, x, z'
'x, -z, -y'
'x, z, y'
'-z, y, -x'
'z, y, x'
'-x, -y+1/2, -z+1/2'
'y, -x+1/2, -z+1/2'
'x, y+1/2, -z+1/2'
'-y, x+1/2, -z+1/2'
'-x, z+1/2, -y+1/2'
'-x, y+1/2, z+1/2'
'-x, -z+1/2, y+1/2'
'-z, -y+1/2, x+1/2'
'x, -y+1/2, z+1/2'
'z, -y+1/2, -x+1/2'
'-z, -x+1/2, -y+1/2'
'-y, -z+1/2, -x+1/2'
'y, z+1/2, -x+1/2'
'-z, x+1/2, y+1/2'
'y, -z+1/2, x+1/2'
'z, x+1/2, -y+1/2'
'z, -x+1/2, y+1/2'
'-y, z+1/2, x+1/2'
'-y, -x+1/2, z+1/2'
'y, x+1/2, z+1/2'
'x, -z+1/2, -y+1/2'
'x, z+1/2, y+1/2'
'-z, y+1/2, -x+1/2'
'z, y+1/2, x+1/2'
'-x+1/2, -y, -z+1/2'
'y+1/2, -x, -z+1/2'
'x+1/2, y, -z+1/2'
'-y+1/2, x, -z+1/2'
'-x+1/2, z, -y+1/2'
'-x+1/2, y, z+1/2'
'-x+1/2, -z, y+1/2'
'-z+1/2, -y, x+1/2'
'x+1/2, -y, z+1/2'
'z+1/2, -y, -x+1/2'
'-z+1/2, -x, -y+1/2'
'-y+1/2, -z, -x+1/2'
'y+1/2, z, -x+1/2'
'-z+1/2, x, y+1/2'
'y+1/2, -z, x+1/2'
'z+1/2, x, -y+1/2'
'z+1/2, -x, y+1/2'
'-y+1/2, z, x+1/2'
'-y+1/2, -x, z+1/2'
'y+1/2, x, z+1/2'
'x+1/2, -z, -y+1/2'
'x+1/2, z, y+1/2'
'-z+1/2, y, -x+1/2'
'z+1/2, y, x+1/2'
'-x+1/2, -y+1/2, -z'
'y+1/2, -x+1/2, -z'
'x+1/2, y+1/2, -z'
'-y+1/2, x+1/2, -z'
'-x+1/2, z+1/2, -y'
'-x+1/2, y+1/2, z'
'-x+1/2, -z+1/2, y'
'-z+1/2, -y+1/2, x'
'x+1/2, -y+1/2, z'
'z+1/2, -y+1/2, -x'
'-z+1/2, -x+1/2, -y'
'-y+1/2, -z+1/2, -x'
'y+1/2, z+1/2, -x'
'-z+1/2, x+1/2, y'
'y+1/2, -z+1/2, x'
'z+1/2, x+1/2, -y'
'z+1/2, -x+1/2, y'
'-y+1/2, z+1/2, x'
'-y+1/2, -x+1/2, z'
'y+1/2, x+1/2, z'
'x+1/2, -z+1/2, -y'
'x+1/2, z+1/2, y'
'-z+1/2, y+1/2, -x'
'z+1/2, y+1/2, x'

_cell_length_a                   43.645(3)
_cell_length_b                   43.645(3)
_cell_length_c                   43.645(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     83137(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Cube
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.358
_exptl_crystal_F_000             8952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.185
_shelx_estimated_absorpt_T_min   0.991
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            194999
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_av_R_equivalents  0.1229
_diffrn_reflns_limit_h_min       -50
_diffrn_reflns_limit_h_max       50
_diffrn_reflns_limit_k_min       -50
_diffrn_reflns_limit_k_max       50
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_theta_min         1.866
_diffrn_reflns_theta_max         24.611
_diffrn_reflns_theta_full        24.611
_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 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3422
_reflns_number_gt                2143
_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.
 
 _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       'APEX2  (Bruker, 2008)'
_computing_cell_refinement       'SAINT+ ver. (Bruker, 2001)'
_computing_data_reduction        'SAINT+ ver. (Bruker, 2001)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] 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         3422
_refine_ls_number_parameters     64
_refine_ls_number_restraints     80
_refine_ls_R_factor_all          0.1597
_refine_ls_R_factor_gt           0.0987
_refine_ls_wR_factor_ref         0.3309
_refine_ls_wR_factor_gt          0.2798
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.291
_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
In1 In 0.2500 0.2500 0.0000 0.0554(5) Uani 1 8 d S T P . .
C7 C 0.32584(8) 0.17416(8) -0.13455(9) 0.115(3) Uani 1 2 d DS T P . .
C8 C 0.35184(8) 0.18655(9) -0.14816(8) 0.122(4) Uani 1 2 d DS T P A .
N1 N 0.36599(16) 0.21056(14) -0.13752(18) 0.132(3) Uani 0.5 1 d D U P A -1
H1 H 0.3824 0.2195 -0.1450 0.158 Uiso 0.5 1 calc R U P A -1
O1 O 0.29576(15) 0.26159(14) -0.02423(14) 0.0668(13) Uani 0.5 1 d D . P B -1
O2 O 0.26782(13) 0.21952(12) -0.03827(12) 0.0668(13) Uani 0.5 1 d D . P B -1
C2 C 0.33808(16) 0.24861(15) -0.06922(17) 0.1062(18) Uani 0.5 1 d D U P A -1
H2 H 0.3422 0.2653 -0.0559 0.127 Uiso 0.5 1 calc R U P A -1
C3 C 0.35654(16) 0.24327(15) -0.09358(18) 0.1062(18) Uani 0.5 1 d D . P A -1
H3 H 0.3736 0.2562 -0.0975 0.127 Uiso 0.5 1 calc R U P A -1
C4 C 0.35021(15) 0.21847(14) -0.11293(14) 0.1062(18) Uani 0.5 1 d D . P A -1
C5 C 0.32522(15) 0.19894(14) -0.10815(13) 0.1062(18) Uani 0.5 1 d D . P A -1
C6 C 0.30684(15) 0.20483(15) -0.08312(15) 0.1062(18) Uani 0.5 1 d D U P A -1
H6 H 0.2898 0.1919 -0.0791 0.127 Uiso 0.5 1 calc R U P A -1
C9 C 0.29018(13) 0.23760(13) -0.03995(12) 0.0668(13) Uani 0.5 1 d D . P B -1
C1 C 0.31265(16) 0.22928(17) -0.06359(15) 0.1062(18) Uani 0.5 1 d D 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
In1 O2 2.272(6) . ?
In1 O1 2.316(6) . ?
In1 C9 2.531(6) . ?
C7 C8 1.3903(15) 61_554 ?
C7 C8 1.3903(15) . ?
C7 C5 1.580(5) . ?
C8 N1 1.302(6) . ?
C8 C7 1.3903(15) 168_554 ?
N1 C4 1.321(8) . ?
O1 C9 1.275(6) . ?
O2 C9 1.257(6) . ?
C2 C3 1.354(7) . ?
C2 C1 1.416(7) . ?
C3 C4 1.401(7) . ?
C4 C5 1.400(6) . ?
C5 C6 1.379(6) . ?
C6 C1 1.389(7) . ?
C9 C1 1.470(6) . ?

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 In1 O1 59.81(17) . . ?
O2 In1 C9 29.72(13) . . ?
O1 In1 C9 30.09(14) . . ?
C8 C7 C8 116.9(3) 61_554 . ?
C8 C7 C5 149.7(3) 61_554 . ?
C8 C7 C5 93.4(3) . . ?
N1 C8 C7 123.2(4) . . ?
N1 C8 C7 113.7(4) . 168_554 ?
C7 C8 C7 123.1(3) . 168_554 ?
C8 N1 C4 104.6(5) . . ?
C9 O1 In1 84.4(4) . . ?
C9 O2 In1 86.6(4) . . ?
C3 C2 C1 120.0(5) . . ?
C2 C3 C4 119.3(5) . . ?
N1 C4 C5 111.6(5) . . ?
N1 C4 C3 126.1(6) . . ?
C5 C4 C3 122.3(5) . . ?
C6 C5 C4 117.2(4) . . ?
C6 C5 C7 135.6(5) . . ?
C4 C5 C7 107.1(4) . . ?
C5 C6 C1 121.5(5) . . ?
O2 C9 O1 129.2(7) . . ?
O2 C9 C1 113.8(6) . . ?
O1 C9 C1 117.0(6) . . ?
O2 C9 In1 63.7(4) . . ?
O1 C9 In1 65.6(4) . . ?
C1 C9 In1 177.5(5) . . ?
C6 C1 C2 119.6(5) . . ?
C6 C1 C9 119.9(6) . . ?
C2 C1 C9 119.9(5) . . ?

_refine_diff_density_max         0.626
_refine_diff_density_min         -3.032
_refine_diff_density_rms         0.080



# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.006 -0.014 -0.008 65986 14024 ' '
_platon_squeeze_details          
;
;


