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

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#                 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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#  from this site to visualise CIF-encoded structures and 
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data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C186 H102 In9 N30 O72 Ru2'
_chemical_formula_weight         5144.50

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'
Ru Ru -1.2594 0.8363 '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   P321

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z'
'x-y, -y, -z'
'-x, -x+y, -z'

_cell_length_a                   15.7780(13)
_cell_length_b                   15.7780(13)
_cell_length_c                   28.032(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     6043.5(12)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       hexagonal-plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2533
_exptl_absorpt_coefficient_mu    1.044
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6802
_exptl_absorpt_correction_T_max  0.8184
_exptl_absorpt_process_details   sadabs

_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            36766
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_sigmaI/netI    0.0516
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         0.73
_diffrn_reflns_theta_max         26.08
_reflns_number_total             7988
_reflns_number_gt                6643
_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)+(0.0627P)²+46.5908P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_number_reflns         7988
_refine_ls_number_parameters     451
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0701
_refine_ls_wR_factor_ref         0.1742
_refine_ls_wR_factor_gt          0.1681
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.070
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ru1 Ru 0.6667 0.3333 0.33683(7) 0.0375(6) Uani 0.852(6) 3 d SP . .
In1 In 1.19531(5) 0.86199(5) 0.31962(3) 0.02967(19) Uani 1 1 d . . .
In2 In 0.47017(6) 0.47017(6) 0.0000 0.0260(2) Uani 1 2 d S . .
O1 O 1.0522(5) 0.2486(4) 0.2601(3) 0.0353(17) Uani 1 1 d . . .
O2 O 1.0010(7) 0.2545(6) 0.1861(3) 0.058(2) Uani 1 1 d . . .
O3 O 0.5791(5) 0.7162(5) 0.3817(3) 0.0411(19) Uani 1 1 d . . .
O4 O 0.5949(7) 0.6833(7) 0.4560(3) 0.056(2) Uani 1 1 d . . .
O5 O 1.0457(6) 0.8257(7) 0.3261(3) 0.053(2) Uani 1 1 d . . .
O6 O 1.0708(7) 0.7906(8) 0.3977(4) 0.083(3) Uani 1 1 d U . .
O7 O 1.1570(5) 0.7087(5) 0.3155(3) 0.0373(18) Uani 1 1 d . . .
O8 O 1.1271(8) 0.7381(6) 0.2406(4) 0.073(3) Uani 1 1 d . . .
O9 O 0.6176(5) 1.0856(5) 0.0607(3) 0.0334(17) Uani 1 1 d . . .
O10 O 0.6676(9) 1.0757(7) 0.1333(3) 0.088(4) Uani 1 1 d . . .
O11 O 0.5067(7) 0.6190(7) 0.0081(3) 0.053(2) Uani 1 1 d . . .
O12 O 0.5442(8) 0.5940(6) 0.0778(3) 0.066(3) Uani 1 1 d . . .
N1 N 1.0964(6) 0.4311(6) 0.2781(3) 0.035(2) Uani 1 1 d . . .
N2 N 0.7656(6) 0.7663(7) 0.3642(4) 0.035(2) Uani 1 1 d . . .
N3 N 0.5692(7) 0.8995(7) 0.0414(3) 0.036(2) Uani 1 1 d . . .
N4 N 0.7155(7) 0.2539(7) 0.2980(3) 0.041(2) Uani 1 1 d U . .
N5 N 0.6127(8) 0.2081(9) 0.3739(3) 0.053(3) Uani 1 1 d . . .
C1 C 1.0359(7) 0.2916(8) 0.2265(4) 0.037(2) Uani 1 1 d . . .
C2 C 1.0539(8) 0.3936(7) 0.2364(4) 0.035(2) Uani 1 1 d . . .
C3 C 1.0285(12) 0.4433(9) 0.2042(4) 0.059(3) Uani 1 1 d . . .
H3A H 0.9937 0.4132 0.1766 0.070 Uiso 1 1 calc R . .
C4 C 1.0572(12) 0.5411(10) 0.2146(5) 0.063(4) Uani 1 1 d . . .
H4A H 1.0475 0.5795 0.1926 0.075 Uiso 1 1 calc R . .
C5 C 1.1001(10) 0.5792(8) 0.2582(5) 0.046(3) Uani 1 1 d . . .
C6 C 1.1175(7) 0.5231(7) 0.2883(4) 0.029(2) Uani 1 1 d . . .
H6A H 1.1457 0.5493 0.3178 0.035 Uiso 1 1 calc R . .
C7 C 1.1311(8) 0.6835(8) 0.2715(5) 0.038(3) Uani 1 1 d . . .
C8 C 0.6261(8) 0.7101(8) 0.4164(5) 0.044(3) Uani 1 1 d . . .
C9 C 0.7295(9) 0.7301(9) 0.4053(4) 0.043(3) Uani 1 1 d . . .
C10 C 0.7813(9) 0.7052(12) 0.4374(5) 0.063(4) Uani 1 1 d . . .
H10A H 0.7532 0.6741 0.4660 0.076 Uiso 1 1 calc R . .
C11 C 0.8752(10) 0.7279(11) 0.4254(5) 0.062(4) Uani 1 1 d . . .
H11A H 0.9127 0.7155 0.4469 0.075 Uiso 1 1 calc R . .
C12 C 0.9147(8) 0.7704(9) 0.3801(5) 0.039(3) Uani 1 1 d . . .
C13 C 0.8563(7) 0.7868(8) 0.3511(4) 0.041(3) Uani 1 1 d . . .
H13A H 0.8792 0.8132 0.3210 0.049 Uiso 1 1 calc R . .
C14 C 1.0192(10) 0.7989(11) 0.3665(7) 0.064(4) Uani 1 1 d U . .
C15 C 0.6362(9) 1.0406(8) 0.0945(4) 0.040(3) Uani 1 1 d . . .
C16 C 0.6129(10) 0.9373(8) 0.0843(3) 0.040(3) Uani 1 1 d . . .
C17 C 0.6337(11) 0.8841(10) 0.1161(5) 0.070(5) Uani 1 1 d . . .
H17A H 0.6596 0.9095 0.1460 0.083 Uiso 1 1 calc R . .
C18 C 0.6161(12) 0.7942(9) 0.1033(5) 0.067(4) Uani 1 1 d . . .
H18A H 0.6345 0.7595 0.1236 0.081 Uiso 1 1 calc R . .
C19 C 0.5704(9) 0.7526(8) 0.0599(5) 0.045(3) Uani 1 1 d . . .
C20 C 0.5474(10) 0.8103(8) 0.0301(4) 0.041(3) Uani 1 1 d . . .
H20A H 0.5157 0.7840 0.0013 0.049 Uiso 1 1 calc R . .
C21 C 0.5418(10) 0.6506(9) 0.0490(5) 0.054(4) Uani 1 1 d . . .
C22 C 0.7677(10) 0.2891(12) 0.2571(5) 0.065(4) Uani 1 1 d . . .
H22A H 0.7860 0.3515 0.2460 0.078 Uiso 1 1 calc R . .
C23 C 0.7926(12) 0.2289(12) 0.2325(6) 0.079(5) Uani 1 1 d . . .
H23A H 0.8306 0.2524 0.2051 0.095 Uiso 1 1 calc R . .
C24 C 0.7630(13) 0.1364(13) 0.2472(6) 0.082(5) Uani 1 1 d . . .
H24A H 0.7791 0.0960 0.2299 0.098 Uiso 1 1 calc R . .
C25 C 0.7063(12) 0.1027(11) 0.2899(7) 0.080(5) Uani 1 1 d . . .
H25A H 0.6837 0.0395 0.3012 0.096 Uiso 1 1 calc R . .
C26 C 0.6869(9) 0.1648(9) 0.3131(5) 0.050(3) Uani 1 1 d . . .
C27 C 0.6266(9) 0.1371(10) 0.3573(5) 0.057(3) Uani 1 1 d . . .
C28 C 0.5950(14) 0.0464(13) 0.3786(7) 0.097(6) Uani 1 1 d . . .
H28A H 0.6085 0.0005 0.3653 0.116 Uiso 1 1 calc R . .
C29 C 0.5401(13) 0.0271(14) 0.4226(7) 0.096(6) Uani 1 1 d . . .
H29A H 0.5158 -0.0322 0.4386 0.115 Uiso 1 1 calc R . .
C30 C 0.5254(12) 0.1021(11) 0.4398(5) 0.069(4) Uani 1 1 d . . .
H30A H 0.4945 0.0936 0.4691 0.083 Uiso 1 1 calc R . .
C31 C 0.5549(9) 0.1882(10) 0.4150(5) 0.056(3) Uani 1 1 d . . .
H31A H 0.5366 0.2326 0.4255 0.067 Uiso 1 1 calc R . .


_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
Ru1 N5 2.007(11) 3_665 ?
Ru1 N5 2.007(11) 2_655 ?
Ru1 N5 2.007(11) . ?
Ru1 N4 2.077(8) . ?
Ru1 N4 2.077(8) 3_665 ?
Ru1 N4 2.077(8) 2_655 ?
In1 O5 2.140(8) . ?
In1 O1 2.143(7) 3_775 ?
In1 O7 2.183(7) . ?
In1 O3 2.227(7) 2_765 ?
In1 N1 2.276(8) 3_775 ?
In1 N2 2.303(8) 2_765 ?
In2 O11 2.132(9) . ?
In2 O11 2.132(9) 4 ?
In2 O9 2.184(8) 6_655 ?
In2 O9 2.184(8) 3_565 ?
In2 N3 2.287(9) 3_565 ?
In2 N3 2.287(9) 6_655 ?
O1 C1 1.260(13) . ?
O1 In1 2.144(7) 2_755 ?
O2 C1 1.268(13) . ?
O3 C8 1.255(15) . ?
O3 In1 2.227(7) 3_675 ?
O4 C8 1.202(14) . ?
O5 C14 1.207(19) . ?
O6 C14 1.245(17) . ?
O7 C7 1.297(14) . ?
O8 C7 1.246(13) . ?
O9 C15 1.302(12) . ?
O9 In2 2.184(8) 2_665 ?
O10 C15 1.208(13) . ?
O11 C21 1.262(16) . ?
O12 C21 1.219(16) . ?
N1 C2 1.330(14) . ?
N1 C6 1.347(13) . ?
N1 In1 2.276(8) 2_755 ?
N2 C9 1.287(15) . ?
N2 C13 1.351(12) . ?
N2 In1 2.303(8) 3_675 ?
N3 C20 1.310(13) . ?
N3 C16 1.367(13) . ?
N3 In2 2.287(9) 2_665 ?
N4 C26 1.313(15) . ?
N4 C22 1.360(15) . ?
N5 C27 1.329(17) . ?
N5 C31 1.404(14) . ?
C1 C2 1.513(14) . ?
C2 C3 1.381(15) . ?
C3 C4 1.404(17) . ?
C4 C5 1.380(16) . ?
C5 C6 1.348(14) . ?
C5 C7 1.511(14) . ?
C8 C9 1.531(16) . ?
C9 C10 1.396(17) . ?
C10 C11 1.381(17) . ?
C11 C12 1.426(18) . ?
C12 C13 1.348(15) . ?
C12 C14 1.525(17) . ?
C15 C16 1.509(14) . ?
C16 C17 1.372(15) . ?
C17 C18 1.350(18) . ?
C18 C19 1.400(17) . ?
C19 C20 1.409(16) . ?
C19 C21 1.469(17) . ?
C22 C23 1.379(19) . ?
C23 C24 1.36(2) . ?
C24 C25 1.43(2) . ?
C25 C26 1.334(18) . ?
C26 C27 1.488(19) . ?
C27 C28 1.39(2) . ?
C28 C29 1.45(2) . ?
C29 C30 1.40(2) . ?
C30 C31 1.383(18) . ?

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
N5 Ru1 N5 95.6(4) 3_665 2_655 ?
N5 Ru1 N5 95.6(4) 3_665 . ?
N5 Ru1 N5 95.6(4) 2_655 . ?
N5 Ru1 N4 169.4(4) 3_665 . ?
N5 Ru1 N4 92.9(4) 2_655 . ?
N5 Ru1 N4 77.3(4) . . ?
N5 Ru1 N4 77.3(4) 3_665 3_665 ?
N5 Ru1 N4 169.4(4) 2_655 3_665 ?
N5 Ru1 N4 92.9(4) . 3_665 ?
N4 Ru1 N4 95.1(4) . 3_665 ?
N5 Ru1 N4 92.9(4) 3_665 2_655 ?
N5 Ru1 N4 77.3(4) 2_655 2_655 ?
N5 Ru1 N4 169.4(4) . 2_655 ?
N4 Ru1 N4 95.1(4) . 2_655 ?
N4 Ru1 N4 95.1(4) 3_665 2_655 ?
O5 In1 O1 84.0(3) . 3_775 ?
O5 In1 O7 92.9(3) . . ?
O1 In1 O7 124.7(3) 3_775 . ?
O5 In1 O3 122.6(3) . 2_765 ?
O1 In1 O3 142.9(3) 3_775 2_765 ?
O7 In1 O3 82.8(3) . 2_765 ?
O5 In1 N1 154.0(4) . 3_775 ?
O1 In1 N1 73.7(3) 3_775 3_775 ?
O7 In1 N1 89.1(3) . 3_775 ?
O3 In1 N1 83.4(3) 2_765 3_775 ?
O5 In1 N2 86.7(3) . 2_765 ?
O1 In1 N2 85.0(3) 3_775 2_765 ?
O7 In1 N2 150.2(3) . 2_765 ?
O3 In1 N2 72.6(3) 2_765 2_765 ?
N1 In1 N2 104.1(3) 3_775 2_765 ?
O11 In2 O11 93.4(5) . 4 ?
O11 In2 O9 85.5(3) . 6_655 ?
O11 In2 O9 121.7(3) 4 6_655 ?
O11 In2 O9 121.7(3) . 3_565 ?
O11 In2 O9 85.5(3) 4 3_565 ?
O9 In2 O9 142.1(4) 6_655 3_565 ?
O11 In2 N3 86.4(4) . 3_565 ?
O11 In2 N3 155.6(3) 4 3_565 ?
O9 In2 N3 82.7(3) 6_655 3_565 ?
O9 In2 N3 74.0(3) 3_565 3_565 ?
O11 In2 N3 155.6(3) . 6_655 ?
O11 In2 N3 86.4(4) 4 6_655 ?
O9 In2 N3 74.0(3) 6_655 6_655 ?
O9 In2 N3 82.7(3) 3_565 6_655 ?
N3 In2 N3 103.6(5) 3_565 6_655 ?
C1 O1 In1 118.7(6) . 2_755 ?
C8 O3 In1 116.7(7) . 3_675 ?
C14 O5 In1 108.5(9) . . ?
C7 O7 In1 105.1(6) . . ?
C15 O9 In2 118.5(6) . 2_665 ?
C21 O11 In2 110.9(8) . . ?
C2 N1 C6 117.7(9) . . ?
C2 N1 In1 113.5(6) . 2_755 ?
C6 N1 In1 128.4(8) . 2_755 ?
C9 N2 C13 122.0(10) . . ?
C9 N2 In1 113.3(7) . 3_675 ?
C13 N2 In1 124.5(8) . 3_675 ?
C20 N3 C16 119.0(10) . . ?
C20 N3 In2 127.3(8) . 2_665 ?
C16 N3 In2 113.4(7) . 2_665 ?
C26 N4 C22 121.6(10) . . ?
C26 N4 Ru1 116.4(8) . . ?
C22 N4 Ru1 121.9(8) . . ?
C27 N5 C31 117.5(12) . . ?
C27 N5 Ru1 118.8(9) . . ?
C31 N5 Ru1 123.6(9) . . ?
O1 C1 O2 125.3(10) . . ?
O1 C1 C2 117.1(9) . . ?
O2 C1 C2 117.5(10) . . ?
N1 C2 C3 123.1(9) . . ?
N1 C2 C1 114.8(9) . . ?
C3 C2 C1 122.0(10) . . ?
C2 C3 C4 117.5(12) . . ?
C5 C4 C3 118.8(11) . . ?
C6 C5 C4 119.1(10) . . ?
C6 C5 C7 119.9(10) . . ?
C4 C5 C7 120.9(10) . . ?
N1 C6 C5 123.5(10) . . ?
O8 C7 O7 124.4(10) . . ?
O8 C7 C5 118.8(11) . . ?
O7 C7 C5 116.8(10) . . ?
O4 C8 O3 126.1(11) . . ?
O4 C8 C9 117.8(12) . . ?
O3 C8 C9 115.8(10) . . ?
N2 C9 C10 120.6(11) . . ?
N2 C9 C8 117.6(10) . . ?
C10 C9 C8 121.7(12) . . ?
C11 C10 C9 118.4(13) . . ?
C10 C11 C12 119.8(12) . . ?
C13 C12 C11 116.7(10) . . ?
C13 C12 C14 122.3(12) . . ?
C11 C12 C14 121.0(12) . . ?
C12 C13 N2 122.3(10) . . ?
O5 C14 O6 124.3(14) . . ?
O5 C14 C12 118.2(12) . . ?
O6 C14 C12 117.4(16) . . ?
O10 C15 O9 123.9(10) . . ?
O10 C15 C16 119.2(9) . . ?
O9 C15 C16 116.8(9) . . ?
N3 C16 C17 121.9(11) . . ?
N3 C16 C15 115.8(9) . . ?
C17 C16 C15 122.3(10) . . ?
C18 C17 C16 118.9(12) . . ?
C17 C18 C19 120.7(11) . . ?
C18 C19 C20 116.8(10) . . ?
C18 C19 C21 119.8(11) . . ?
C20 C19 C21 123.2(12) . . ?
N3 C20 C19 122.5(11) . . ?
O12 C21 O11 118.7(12) . . ?
O12 C21 C19 124.1(14) . . ?
O11 C21 C19 117.1(13) . . ?
N4 C22 C23 117.6(14) . . ?
C24 C23 C22 121.8(16) . . ?
C23 C24 C25 118.0(16) . . ?
C26 C25 C24 117.9(15) . . ?
N4 C26 C25 123.1(14) . . ?
N4 C26 C27 114.2(10) . . ?
C25 C26 C27 122.6(13) . . ?
N5 C27 C28 126.2(15) . . ?
N5 C27 C26 113.2(11) . . ?
C28 C27 C26 120.5(15) . . ?
C27 C28 C29 116.8(17) . . ?
C30 C29 C28 116.7(14) . . ?
C31 C30 C29 122.7(14) . . ?
C30 C31 N5 119.6(13) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        26.08
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         2.734
_refine_diff_density_min         -2.413
_refine_diff_density_rms         0.156

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 -0.138 -0.108 -0.001 1976 635 ' '
_platon_squeeze_details          
;
A. L. Spek, J. Appl. Crystallogr., 2003, 36, 7-13.
A. L. Spek, Acta Crystallogr., 2009, D65, 148-155
;

_database_code_depnum_ccdc_archive 'CCDC 997132'
#######################################################################
#
#                 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_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H6 In N2 O8'
_chemical_formula_weight         445.03

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                   15.7069(13)
_cell_length_b                   15.7069(13)
_cell_length_c                   52.887(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     11299(2)
_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       hexagonal-plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3906
_exptl_absorpt_coefficient_mu    0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7275
_exptl_absorpt_correction_T_max  0.8295
_exptl_absorpt_process_details   sadabs

_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            22233
_diffrn_reflns_av_R_equivalents  0.1186
_diffrn_reflns_av_sigmaI/netI    0.0651
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -62
_diffrn_reflns_limit_l_max       64
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         26.04
_reflns_number_total             2486
_reflns_number_gt                1667
_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)+(0.0295P)²+0.0000P] 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_number_reflns         2486
_refine_ls_number_parameters     114
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0744
_refine_ls_wR_factor_gt          0.0680
_refine_ls_goodness_of_fit_ref   0.868
_refine_ls_restrained_S_all      0.868
_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 1.13481(2) 0.80148(2) 0.0833 0.04063(13) Uani 1 2 d S . .
O1 O 1.12978(19) 0.70997(18) 0.05130(5) 0.0490(7) Uani 1 1 d . . .
O2 O 1.0691(2) 0.6578(2) 0.01286(5) 0.0845(11) Uani 1 1 d . . .
O3 O 0.7168(2) 0.7929(2) 0.04338(6) 0.0729(9) Uani 1 1 d . . .
O4 O 0.78362(19) 0.83109(19) 0.08120(5) 0.0559(7) Uani 1 1 d . . .
N1 N 0.9961(2) 0.7631(2) 0.06111(5) 0.0412(7) Uani 1 1 d . . .
C1 C 1.0693(3) 0.6939(3) 0.03342(8) 0.0536(10) Uani 1 1 d . . .
C2 C 0.9904(3) 0.7206(3) 0.03869(7) 0.0473(10) Uani 1 1 d . . .
C3 C 0.9160(3) 0.7019(3) 0.02205(7) 0.0622(12) Uani 1 1 d . . .
H3A H 0.9124 0.6720 0.0066 0.075 Uiso 1 1 calc R . .
C4 C 0.8466(3) 0.7274(3) 0.02826(8) 0.0629(12) Uani 1 1 d . . .
H4A H 0.7961 0.7151 0.0170 0.076 Uiso 1 1 calc R . .
C5 C 0.8526(3) 0.7712(3) 0.05121(7) 0.0478(10) Uani 1 1 d . . .
C6 C 0.9287(3) 0.7873(3) 0.06708(7) 0.0449(9) Uani 1 1 d . . .
H6A H 0.9331 0.8165 0.0827 0.054 Uiso 1 1 calc R . .
C7 C 0.7787(3) 0.7996(3) 0.05864(9) 0.0529(11) 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
In1 O4 2.158(2) 17_664 ?
In1 O4 2.158(2) 2_765 ?
In1 O1 2.197(2) 16_544 ?
In1 O1 2.197(2) . ?
In1 N1 2.276(3) 16_544 ?
In1 N1 2.276(3) . ?
O1 C1 1.273(4) . ?
O2 C1 1.225(4) . ?
O3 C7 1.227(4) . ?
O4 C7 1.279(4) . ?
O4 In1 2.158(2) 3_675 ?
N1 C6 1.330(4) . ?
N1 C2 1.341(4) . ?
C1 C2 1.521(5) . ?
C2 C3 1.372(5) . ?
C3 C4 1.375(5) . ?
C4 C5 1.375(5) . ?
C5 C6 1.376(5) . ?
C5 C7 1.490(5) . ?

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 In1 O4 95.28(14) 17_664 2_765 ?
O4 In1 O1 125.93(10) 17_664 16_544 ?
O4 In1 O1 83.00(10) 2_765 16_544 ?
O4 In1 O1 83.00(10) 17_664 . ?
O4 In1 O1 125.93(10) 2_765 . ?
O1 In1 O1 139.63(13) 16_544 . ?
O4 In1 N1 86.73(10) 17_664 16_544 ?
O4 In1 N1 151.74(10) 2_765 16_544 ?
O1 In1 N1 73.25(9) 16_544 16_544 ?
O1 In1 N1 82.32(10) . 16_544 ?
O4 In1 N1 151.74(10) 17_664 . ?
O4 In1 N1 86.73(10) 2_765 . ?
O1 In1 N1 82.32(10) 16_544 . ?
O1 In1 N1 73.25(9) . . ?
N1 In1 N1 104.63(14) 16_544 . ?
C1 O1 In1 118.8(2) . . ?
C7 O4 In1 104.5(2) . 3_675 ?
C6 N1 C2 119.2(3) . . ?
C6 N1 In1 126.5(2) . . ?
C2 N1 In1 113.9(2) . . ?
O2 C1 O1 125.5(4) . . ?
O2 C1 C2 118.4(4) . . ?
O1 C1 C2 116.1(3) . . ?
N1 C2 C3 120.8(3) . . ?
N1 C2 C1 116.0(3) . . ?
C3 C2 C1 123.2(4) . . ?
C2 C3 C4 119.9(4) . . ?
C3 C4 C5 119.4(4) . . ?
C4 C5 C6 117.8(4) . . ?
C4 C5 C7 121.0(4) . . ?
C6 C5 C7 121.3(4) . . ?
N1 C6 C5 123.0(3) . . ?
O3 C7 O4 122.7(4) . . ?
O3 C7 C5 120.2(4) . . ?
O4 C7 C5 117.1(4) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.04
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.065

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 -0.060 -0.050 -0.002 5829 1634 ' '
_platon_squeeze_details          
;
A. L. Spek, J. Appl. Crystallogr., 2003, 36, 7-13.
A. L. Spek, Acta Crystallogr., 2009, D65, 148-155
;
_database_code_depnum_ccdc_archive 'CCDC 997133'
