# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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data_r-3c

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C56 H95 In N6 O16'
_chemical_formula_weight         1223.20

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'

_symmetry_cell_setting           Trigonal
_symmetry_space_group_name_H-M   R-3c

loop_
_symmetry_equiv_pos_as_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+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'
'y+2/3, x+1/3, -z+5/6'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'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'
'y+1/3, x+2/3, -z+7/6'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'-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+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'
'-y+2/3, -x+1/3, z-1/6'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-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'
'-y+1/3, -x+2/3, z+1/6'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'

_cell_length_a                   38.2369(10)
_cell_length_b                   38.2369(10)
_cell_length_c                   22.7356(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     28787.4(19)
_cell_formula_units_Z            18
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             11700
_exptl_absorpt_coefficient_mu    0.436
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5683
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   Process-auto

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            69588
_diffrn_reflns_av_R_equivalents  0.0947
_diffrn_reflns_av_sigmaI/netI    0.0790
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       50
_diffrn_reflns_limit_k_min       -50
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.07
_diffrn_reflns_theta_max         28.29
_reflns_number_total             7969
_reflns_number_gt                3195
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

The Following ALERTS were generated by PLATON checkcif
Alert level A
CHEMW03_ALERT_2_A ALERT: The ratio of given/expected molecular weight as
calculated from the _atom_site* data lies outside
the range 0.90 <> 1.10 
From the CIF: _chemical_formula_weight 1223.20
TEST: Calculate formula weight from _atom_site_*
atom mass num sum
C 12.01 24.00 288.26
H 1.01 15.00 15.12
N 14.01 1.00 14.01
O 16.00 8.00 127.99
In 114.82 1.00 114.82
Calculated formula weight 560.20
Alert level A
PLAT051_ALERT_1_A Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by . 11.16 Perc.

Response: These alerts may caused by the difference of the calculated and reported formula. 
          The reported formula includes the solvent molecules (Et2NH2+, DEF and C2H5OH) of the PLATON/squeeze calculation.
          These molecules were not included in the model.

;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0231P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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_number_reflns         7969
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1513
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.0878
_refine_ls_wR_factor_gt          0.0788
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
In1 In 0.411383(7) 0.078050(7) 0.0833 0.07793(13) Uani 1 2 d S . .
N1 N 0.6667 0.11489(10) 0.0833 0.0969(11) Uani 1 2 d S . .
O1 O 0.46590(6) 0.07451(6) 0.11442(11) 0.0982(7) Uani 1 1 d . . .
O2 O 0.46951(6) 0.10389(6) 0.03052(10) 0.1056(7) Uani 1 1 d . . .
O3 O 0.62293(6) -0.05040(7) -0.00306(9) 0.1057(7) Uani 1 1 d . . .
O4 O 0.60590(7) -0.01060(7) -0.04566(10) 0.1166(8) Uani 1 1 d . . .
C1 C 0.48486(10) 0.09212(9) 0.07065(19) 0.0920(11) Uani 1 1 d . . .
C2 C 0.52770(9) 0.10145(9) 0.06055(17) 0.0930(10) Uani 1 1 d . . .
C3 C 0.54957(10) 0.12221(10) 0.01211(17) 0.1176(12) Uani 1 1 d . . .
H3 H 0.5379 0.1308 -0.0162 0.141 Uiso 1 1 calc R . .
C4 C 0.58938(10) 0.13056(10) 0.00518(17) 0.1209(12) Uani 1 1 d . . .
H4 H 0.6043 0.1456 -0.0271 0.145 Uiso 1 1 calc R . .
C5 C 0.60677(8) 0.11705(8) 0.04489(17) 0.0875(9) Uani 1 1 d . . .
C6 C 0.58417(9) 0.09582(9) 0.09221(16) 0.1034(11) Uani 1 1 d . . .
H6 H 0.5953 0.0862 0.1197 0.124 Uiso 1 1 calc R . .
C7 C 0.54528(9) 0.08821(8) 0.10053(15) 0.1049(10) Uani 1 1 d . . .
H7 H 0.5309 0.0740 0.1336 0.126 Uiso 1 1 calc R . .
C8 C 0.64917(8) 0.12698(9) 0.03513(15) 0.1048(11) Uani 1 1 d . . .
H8A H 0.6503 0.1139 -0.0008 0.126 Uiso 1 1 calc R . .
H8B H 0.6657 0.1559 0.0293 0.126 Uiso 1 1 calc R . .
C9 C 0.6667 0.07817(12) 0.0833 0.0832(11) Uani 1 2 d S . .
C10 C 0.64557(7) 0.04864(9) 0.04156(13) 0.0870(9) Uani 1 1 d . . .
H10 H 0.6308 0.0531 0.0130 0.104 Uiso 1 1 calc R . .
C11 C 0.64596(8) 0.01348(9) 0.04137(14) 0.0785(8) Uani 1 1 d . . .
C12 C 0.6667 0.00575(11) 0.0833 0.0789(12) Uani 1 2 d S . .
H12 H 0.6667 -0.0186 0.0833 0.095 Uiso 1 2 calc SR . .
C13 C 0.62341(9) -0.01672(11) -0.00542(17) 0.0919(10) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
In1 0.06661(15) 0.06661(15) 0.1043(2) 0.00543(9) -0.00543(9) 0.03608(17)
N1 0.052(2) 0.0694(19) 0.164(4) 0.0009(11) 0.002(2) 0.0258(10)
O1 0.0637(14) 0.0958(16) 0.133(2) 0.0181(13) 0.0093(13) 0.0382(12)
O2 0.0753(14) 0.1036(16) 0.144(2) 0.0042(14) -0.0039(13) 0.0495(13)
O3 0.0887(15) 0.1015(16) 0.1253(18) -0.0211(14) -0.0204(13) 0.0464(13)
O4 0.1196(18) 0.1101(18) 0.1113(19) -0.0048(14) -0.0324(15) 0.0508(15)
C1 0.064(3) 0.071(2) 0.140(4) -0.008(2) -0.015(2) 0.0325(19)
C2 0.062(2) 0.084(2) 0.134(3) 0.023(2) 0.006(2) 0.0369(18)
C3 0.085(3) 0.139(3) 0.145(3) 0.046(3) 0.018(2) 0.068(2)
C4 0.078(2) 0.130(3) 0.156(4) 0.045(2) 0.024(2) 0.053(2)
C5 0.0516(19) 0.068(2) 0.138(3) 0.0147(19) 0.006(2) 0.0269(17)
C6 0.058(2) 0.097(2) 0.153(3) 0.028(2) -0.003(2) 0.0370(18)
C7 0.066(2) 0.098(2) 0.144(3) 0.036(2) 0.008(2) 0.0364(19)
C8 0.060(2) 0.078(2) 0.169(3) 0.019(2) 0.011(2) 0.0289(17)
C9 0.039(2) 0.065(2) 0.136(4) -0.0019(13) -0.004(3) 0.0197(12)
C10 0.0519(18) 0.069(2) 0.126(3) 0.011(2) -0.0060(17) 0.0195(16)
C11 0.0611(19) 0.067(2) 0.095(2) -0.016(2) -0.0167(17) 0.0227(16)
C12 0.065(3) 0.077(2) 0.091(3) -0.0018(12) -0.004(2) 0.0324(13)
C13 0.070(2) 0.093(3) 0.111(3) 0.016(3) 0.020(2) 0.040(2)

_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 O3 2.187(2) 34 ?
In1 O3 2.187(2) 19_655 ?
In1 O1 2.268(2) 16_544 ?
In1 O1 2.268(2) . ?
In1 O2 2.2720(19) 16_544 ?
In1 O2 2.2721(19) . ?
In1 O4 2.473(2) 34 ?
In1 O4 2.473(2) 19_655 ?
In1 C1 2.599(3) 16_544 ?
In1 C1 2.599(3) . ?
In1 C13 2.699(4) 19_655 ?
In1 C13 2.699(4) 34 ?
N1 C9 1.404(5) . ?
N1 C8 1.473(3) . ?
N1 C8 1.473(3) 18_654 ?
O1 C1 1.217(4) . ?
O2 C1 1.282(3) . ?
O3 C13 1.280(3) . ?
O3 In1 2.187(2) 19_655 ?
O4 C13 1.223(3) . ?
O4 In1 2.473(2) 19_655 ?
C1 C2 1.510(4) . ?
C2 C7 1.369(4) . ?
C2 C3 1.371(4) . ?
C3 C4 1.399(4) . ?
C4 C5 1.367(4) . ?
C5 C6 1.364(4) . ?
C5 C8 1.485(3) . ?
C6 C7 1.378(3) . ?
C9 C10 1.385(3) . ?
C9 C10 1.385(3) 18_654 ?
C10 C11 1.352(3) . ?
C11 C12 1.363(3) . ?
C11 C13 1.488(4) . ?
C12 C11 1.363(3) 18_654 ?
C13 In1 2.699(4) 19_655 ?

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
O3 In1 O3 114.40(12) 34 19_655 ?
O3 In1 O1 125.34(8) 34 16_544 ?
O3 In1 O1 83.52(9) 19_655 16_544 ?
O3 In1 O1 83.52(9) 34 . ?
O3 In1 O1 125.33(8) 19_655 . ?
O1 In1 O1 129.11(11) 16_544 . ?
O3 In1 O2 89.38(8) 34 16_544 ?
O3 In1 O2 140.92(9) 19_655 16_544 ?
O1 In1 O2 57.47(7) 16_544 16_544 ?
O1 In1 O2 86.02(8) . 16_544 ?
O3 In1 O2 140.92(9) 34 . ?
O3 In1 O2 89.38(8) 19_655 . ?
O1 In1 O2 86.02(8) 16_544 . ?
O1 In1 O2 57.47(7) . . ?
O2 In1 O2 90.09(10) 16_544 . ?
O3 In1 O4 54.83(7) 34 34 ?
O3 In1 O4 82.32(7) 19_655 34 ?
O1 In1 O4 79.64(8) 16_544 34 ?
O1 In1 O4 137.96(8) . 34 ?
O2 In1 O4 87.92(7) 16_544 34 ?
O2 In1 O4 164.13(8) . 34 ?
O3 In1 O4 82.32(7) 34 19_655 ?
O3 In1 O4 54.83(7) 19_655 19_655 ?
O1 In1 O4 137.96(8) 16_544 19_655 ?
O1 In1 O4 79.64(8) . 19_655 ?
O2 In1 O4 164.12(8) 16_544 19_655 ?
O2 In1 O4 87.92(7) . 19_655 ?
O4 In1 O4 98.16(11) 34 19_655 ?
O3 In1 C1 109.43(10) 34 16_544 ?
O3 In1 C1 111.41(11) 19_655 16_544 ?
O1 In1 C1 27.92(8) 16_544 16_544 ?
O1 In1 C1 109.28(10) . 16_544 ?
O2 In1 C1 29.55(9) 16_544 16_544 ?
O2 In1 C1 87.69(8) . 16_544 ?
O4 In1 C1 82.83(9) 34 16_544 ?
O4 In1 C1 165.61(11) 19_655 16_544 ?
O3 In1 C1 111.41(11) 34 . ?
O3 In1 C1 109.43(10) 19_655 . ?
O1 In1 C1 109.28(10) 16_544 . ?
O1 In1 C1 27.92(8) . . ?
O2 In1 C1 87.69(8) 16_544 . ?
O2 In1 C1 29.55(9) . . ?
O4 In1 C1 165.61(11) 34 . ?
O4 In1 C1 82.83(9) 19_655 . ?
C1 In1 C1 99.81(13) 16_544 . ?
O3 In1 C13 98.39(9) 34 19_655 ?
O3 In1 C13 27.93(8) 19_655 19_655 ?
O1 In1 C13 111.33(11) 16_544 19_655 ?
O1 In1 C13 102.78(10) . 19_655 ?
O2 In1 C13 168.81(10) 16_544 19_655 ?
O2 In1 C13 88.92(8) . 19_655 ?
O4 In1 C13 89.99(7) 34 19_655 ?
O4 In1 C13 26.91(7) 19_655 19_655 ?
C1 In1 C13 139.25(13) 16_544 19_655 ?
C1 In1 C13 96.86(9) . 19_655 ?
O3 In1 C13 27.93(8) 34 34 ?
O3 In1 C13 98.39(9) 19_655 34 ?
O1 In1 C13 102.78(10) 16_544 34 ?
O1 In1 C13 111.33(11) . 34 ?
O2 In1 C13 88.92(8) 16_544 34 ?
O2 In1 C13 168.80(10) . 34 ?
O4 In1 C13 26.91(7) 34 34 ?
O4 In1 C13 89.99(7) 19_655 34 ?
C1 In1 C13 96.86(10) 16_544 34 ?
C1 In1 C13 139.25(13) . 34 ?
C13 In1 C13 94.19(12) 19_655 34 ?
C9 N1 C8 122.72(17) . . ?
C9 N1 C8 122.72(17) . 18_654 ?
C8 N1 C8 114.6(3) . 18_654 ?
C1 O1 In1 91.3(2) . . ?
C1 O2 In1 89.5(2) . . ?
C13 O3 In1 98.9(2) . 19_655 ?
C13 O4 In1 86.9(2) . 19_655 ?
O1 C1 O2 121.7(3) . . ?
O1 C1 C2 122.1(3) . . ?
O2 C1 C2 116.2(4) . . ?
O1 C1 In1 60.76(18) . . ?
O2 C1 In1 60.96(16) . . ?
C2 C1 In1 177.2(3) . . ?
C7 C2 C3 118.5(3) . . ?
C7 C2 C1 119.1(3) . . ?
C3 C2 C1 122.3(3) . . ?
C2 C3 C4 120.1(3) . . ?
C5 C4 C3 121.3(3) . . ?
C6 C5 C4 117.6(3) . . ?
C6 C5 C8 123.7(3) . . ?
C4 C5 C8 118.7(3) . . ?
C5 C6 C7 122.0(3) . . ?
C2 C7 C6 120.5(3) . . ?
N1 C8 C5 114.7(2) . . ?
C10 C9 C10 116.8(4) . 18_654 ?
C10 C9 N1 121.6(2) . . ?
C10 C9 N1 121.6(2) 18_654 . ?
C11 C10 C9 121.4(3) . . ?
C10 C11 C12 120.7(3) . . ?
C10 C11 C13 118.9(3) . . ?
C12 C11 C13 120.4(3) . . ?
C11 C12 C11 119.0(4) . 18_654 ?
O4 C13 O3 119.3(4) . . ?
O4 C13 C11 123.1(3) . . ?
O3 C13 C11 117.5(3) . . ?
O4 C13 In1 66.2(2) . 19_655 ?
O3 C13 In1 53.17(18) . 19_655 ?
C11 C13 In1 170.5(3) . 19_655 ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        28.29
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.574
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.036
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 -0.009 -0.007 -0.002 21601 6913 ' '
_platon_squeeze_details          
;
The remaining solvent molecules were disordered and assigned as 18 Et2NH2+ ion, 72 DEF molecules,
72 ethanol molecules per unit cell, which were determined by TGA,
elemental analysis and SQUEEZE results. The contributions of these disordered solvents to
the scattering values have been removed by using the PLATON SQUEEZE program. We can see from 
the SQUEEZE that some 6913 electrons were removed from the unit cell, or some 6913/18 = 384 electrons 
per formula unit. This total includes 42 electrons of the Et2NH2+ ion and other electrons (342e) from 
disordered solvent, approximately 4(DEF) + 4(EtOH) in the channel. From the calculation and
related information (The CHN and TGA), the formula unit should include 4 DEF, 4 C2H5OH (56e*4+26e*4=328e).
Anal. Cald. for C56H95N6O16In: C, 54.99; H, 7.83; N, 6.87; found: C, 53.86; H, 6.90; N, 7.89.
;
_database_code_depnum_ccdc_archive 'CCDC 918529'