# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_InOF-8

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H24 Cu6 I6 In3 N6 O16'
_chemical_formula_weight         2283.71

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
In In 0.0822 5.0449 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           trigonal
_symmetry_space_group_name_H-M   P6/mcc

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x-y, x, z'
'-y, x-y, z'
'-x, -y, z'
'-x+y, -x, z'
'y, -x+y, z'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'y, x, -z+1/2'
'-y, -x, -z+1/2'
'-x+y, y, -z+1/2'
'x, x-y, -z+1/2'
'-x, -y, -z'
'-x+y, -x, -z'
'y, -x+y, -z'
'x, y, -z'
'x-y, x, -z'
'-y, x-y, -z'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-y, -x, z-1/2'
'y, x, z-1/2'
'x-y, -y, z-1/2'
'-x, -x+y, z-1/2'

_cell_length_a                   21.9173(4)
_cell_length_b                   21.9173(4)
_cell_length_c                   28.2685(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     11760.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             4196
_exptl_absorpt_coefficient_mu    18.407
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.2161
_exptl_absorpt_correction_T_max  0.4047
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\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            25786
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_sigmaI/netI    0.0199
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.90
_diffrn_reflns_theta_max         73.14
_reflns_number_total             4004
_reflns_number_gt                2954
_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 F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1668P)²+55.1877P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4004
_refine_ls_number_parameters     114
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.1128
_refine_ls_R_factor_gt           0.0964
_refine_ls_wR_factor_ref         0.3051
_refine_ls_wR_factor_gt          0.2853
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_restrained_S_all      1.177
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

# SQUEEZE RESULTS (APPEND TO CIF)
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
1 -0.004 -0.002 -0.006 6321.0 537.2
2 0.333 0.667 0.250 229.6 40.9
3 0.333 0.667 0.750 229.5 44.1
4 0.667 0.333 0.250 229.4 42.7
5 0.667 0.333 0.750 229.5 45.8
_platon_squeeze_details          
;
;

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 0.23073(5) 0.64358(5) 0.5000 0.0501(4) Uani 1 2 d S . .
O3 O 0.3333 0.6667 0.5000 0.052(3) Uani 1 6 d S . .
O1 O 0.2031(4) 0.5665(4) 0.4435(2) 0.0618(18) Uani 1 1 d . . .
O4 O 0.1240(9) 0.6191(8) 0.5000 0.117(6) Uani 1 2 d S . .
O2 O 0.2810(5) 0.5276(6) 0.4454(3) 0.092(3) Uani 1 1 d . . .
I1 I 0.07657(8) 0.46421(9) 0.19169(5) 0.1720(10) Uani 1 1 d . . .
Cu1 Cu 0.05067(13) 0.4825(2) 0.28233(8) 0.1471(15) Uani 1 1 d . . .
C6 C 0.2303(5) 0.5320(7) 0.4283(4) 0.071(3) Uani 1 1 d . . .
C1 C 0.1498(7) 0.5028(11) 0.3592(5) 0.113(7) Uani 1 1 d U . .
H1 H 0.1376 0.5362 0.3705 0.136 Uiso 1 1 calc R . .
C5 C 0.1327(13) 0.4107(13) 0.3079(9) 0.137(7) Uani 1 1 d U . .
H5 H 0.1015 0.3753 0.2866 0.164 Uiso 1 1 calc R . .
C2 C 0.1988(7) 0.4894(12) 0.3856(6) 0.120(7) Uani 1 1 d . . .
N1 N 0.1213(9) 0.4669(8) 0.3178(6) 0.111(4) Uani 1 1 d U . .
C3 C 0.2229(15) 0.4468(12) 0.3682(10) 0.149(7) Uani 1 1 d U . .
H3 H 0.2614 0.4448 0.3820 0.178 Uiso 1 1 calc R . .
C4 C 0.1845(17) 0.4044(16) 0.3265(12) 0.180(10) Uani 1 1 d U . .
H4 H 0.1971 0.3724 0.3131 0.216 Uiso 1 1 calc R . .

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 0.0618(6) 0.0652(6) 0.0230(5) 0.000 0.000 0.0316(4)
O3 0.065(5) 0.065(5) 0.026(6) 0.000 0.000 0.032(3)
O1 0.072(4) 0.080(5) 0.025(3) -0.012(3) 0.002(3) 0.032(4)
O4 0.105(11) 0.069(8) 0.186(18) 0.000 0.000 0.050(8)
O2 0.086(6) 0.120(8) 0.068(5) -0.045(5) -0.022(4) 0.049(6)
I1 0.1354(11) 0.1684(13) 0.0907(9) -0.0815(9) 0.0426(7) -0.0153(9)
Cu1 0.0852(14) 0.295(4) 0.0736(14) -0.101(2) -0.0418(11) 0.104(2)
C6 0.047(5) 0.097(8) 0.046(6) -0.026(6) -0.005(4) 0.018(5)
C1 0.068(7) 0.201(18) 0.077(8) -0.067(10) -0.006(6) 0.072(10)
C5 0.137(7) 0.137(7) 0.137(7) -0.0004(10) -0.0002(10) 0.069(4)
C2 0.061(7) 0.217(19) 0.084(9) -0.092(12) -0.025(7) 0.069(10)
N1 0.111(4) 0.111(4) 0.110(4) -0.0018(10) 0.0000(10) 0.055(2)
C3 0.148(8) 0.152(9) 0.147(9) -0.015(5) -0.002(5) 0.075(6)
C4 0.180(10) 0.180(10) 0.180(10) -0.0003(10) -0.0001(10) 0.090(5)

_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 2.0434(9) . ?
In1 O4 2.122(17) . ?
In1 O2 2.159(8) 14_566 ?
In1 O2 2.159(8) 5_565 ?
In1 O1 2.179(6) . ?
In1 O1 2.179(6) 16_556 ?
O3 In1 2.0434(9) 14_566 ?
O3 In1 2.0434(9) 3_665 ?
O1 C6 1.250(15) . ?
O2 C6 1.258(15) . ?
O2 In1 2.159(8) 3_665 ?
I1 Cu1 2.616(3) 8 ?
I1 Cu1 2.698(2) . ?
I1 Cu1 2.710(4) 12_565 ?
Cu1 N1 2.013(17) . ?
Cu1 I1 2.616(3) 8 ?
Cu1 Cu1 2.620(8) 12_565 ?
Cu1 Cu1 2.654(4) 8 ?
Cu1 Cu1 2.687(5) 4_565 ?
Cu1 I1 2.710(4) 12_565 ?
C6 C2 1.470(15) . ?
C1 N1 1.373(19) . ?
C1 C2 1.45(2) . ?
C5 C4 1.32(4) . ?
C5 N1 1.40(3) . ?
C2 C3 1.37(3) . ?
C3 C4 1.48(4) . ?

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 O4 179.7(4) . . ?
O3 In1 O2 94.3(3) . 14_566 ?
O4 In1 O2 85.9(4) . 14_566 ?
O3 In1 O2 94.3(3) . 5_565 ?
O4 In1 O2 85.9(4) . 5_565 ?
O2 In1 O2 91.3(6) 14_566 5_565 ?
O3 In1 O1 92.1(2) . . ?
O4 In1 O1 87.7(3) . . ?
O2 In1 O1 173.5(4) 14_566 . ?
O2 In1 O1 86.8(3) 5_565 . ?
O3 In1 O1 92.1(2) . 16_556 ?
O4 In1 O1 87.7(3) . 16_556 ?
O2 In1 O1 86.8(3) 14_566 16_556 ?
O2 In1 O1 173.5(4) 5_565 16_556 ?
O1 In1 O1 94.3(4) . 16_556 ?
In1 O3 In1 120.0 . 14_566 ?
In1 O3 In1 120.000(1) . 3_665 ?
In1 O3 In1 120.0 14_566 3_665 ?
C6 O1 In1 133.5(7) . . ?
C6 O2 In1 131.8(8) . 3_665 ?
Cu1 I1 Cu1 59.90(8) 8 . ?
Cu1 I1 Cu1 60.58(11) 8 12_565 ?
Cu1 I1 Cu1 57.95(14) . 12_565 ?
N1 Cu1 I1 109.3(5) . 8 ?
N1 Cu1 Cu1 138.2(5) . 12_565 ?
I1 Cu1 Cu1 112.56(8) 8 12_565 ?
N1 Cu1 Cu1 145.7(5) . 8 ?
I1 Cu1 Cu1 61.58(10) 8 8 ?
Cu1 Cu1 Cu1 61.27(9) 12_565 8 ?
N1 Cu1 Cu1 149.8(5) . 4_565 ?
I1 Cu1 Cu1 61.45(10) 8 4_565 ?
Cu1 Cu1 Cu1 59.98(14) 12_565 4_565 ?
Cu1 Cu1 Cu1 58.74(16) 8 4_565 ?
N1 Cu1 I1 102.2(5) . . ?
I1 Cu1 I1 111.62(10) 8 . ?
Cu1 Cu1 I1 61.26(9) 12_565 . ?
Cu1 Cu1 I1 58.52(10) 8 . ?
Cu1 Cu1 I1 107.93(7) 4_565 . ?
N1 Cu1 I1 105.6(5) . 12_565 ?
I1 Cu1 I1 109.82(11) 8 12_565 ?
Cu1 Cu1 I1 60.78(13) 12_565 12_565 ?
Cu1 Cu1 I1 108.55(5) 8 12_565 ?
Cu1 Cu1 I1 57.97(15) 4_565 12_565 ?
I1 Cu1 I1 117.68(15) . 12_565 ?
O1 C6 O2 128.5(9) . . ?
O1 C6 C2 116.8(11) . . ?
O2 C6 C2 114.7(12) . . ?
N1 C1 C2 119.5(15) . . ?
C4 C5 N1 124(3) . . ?
C3 C2 C1 121.8(16) . . ?
C3 C2 C6 120.6(18) . . ?
C1 C2 C6 117.0(15) . . ?
C1 N1 C5 116.4(18) . . ?
C1 N1 Cu1 119.7(13) . . ?
C5 N1 Cu1 122.6(14) . . ?
C2 C3 C4 115(3) . . ?
C5 C4 C3 120(3) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        73.14
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         2.598
_refine_diff_density_min         -1.816
_refine_diff_density_rms         0.186

_vrf_PLAT342_InOF-8              
;
PROBLEM: Low Bond Precision on  C-C Bonds        0.0360 Ang. 

RESPONSE: Though we tried our best to collect the diffraction data  
and refine the structure, the weak diffractions and too many 
exterior nonmetalllic atoms result in Low Bond Precision on  C-C Bonds.
;
_database_code_depnum_ccdc_archive 'CCDC 998993'
