# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2010

data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_author_name                'Guangshan Zhu'
_publ_contact_author_name        'Guangshan Zhu'
_publ_contact_author_email       zhugs@mail.jlu.edu.cn

data_JUC-77
_database_code_depnum_ccdc_archive 'CCDC 773451'
#TrackingRef '- JUC-77.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H9 In N0 O6'
_chemical_formula_weight         388.03

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           orthorhombic
_symmetry_space_group_name_H-M   Fddd

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+3/4, -y+3/4, z'
'-x+3/4, y, -z+3/4'
'x, -y+3/4, -z+3/4'
'x, y+1/2, z+1/2'
'-x+3/4, -y+5/4, z+1/2'
'-x+3/4, y+1/2, -z+5/4'
'x, -y+5/4, -z+5/4'
'x+1/2, y, z+1/2'
'-x+5/4, -y+3/4, z+1/2'
'-x+5/4, y, -z+5/4'
'x+1/2, -y+3/4, -z+5/4'
'x+1/2, y+1/2, z'
'-x+5/4, -y+5/4, z'
'-x+5/4, y+1/2, -z+3/4'
'x+1/2, -y+5/4, -z+3/4'
'-x, -y, -z'
'x-3/4, y-3/4, -z'
'x-3/4, -y, z-3/4'
'-x, y-3/4, z-3/4'
'-x, -y+1/2, -z+1/2'
'x-3/4, y-1/4, -z+1/2'
'x-3/4, -y+1/2, z-1/4'
'-x, y-1/4, z-1/4'
'-x+1/2, -y, -z+1/2'
'x-1/4, y-3/4, -z+1/2'
'x-1/4, -y, z-1/4'
'-x+1/2, y-3/4, z-1/4'
'-x+1/2, -y+1/2, -z'
'x-1/4, y-1/4, -z'
'x-1/4, -y+1/2, z-3/4'
'-x+1/2, y-1/4, z-3/4'

_cell_length_a                   19.2396(9)
_cell_length_b                   20.3017(9)
_cell_length_c                   46.143(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     18023.4(14)
_cell_formula_units_Z            32
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5357
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      28.29

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.144
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             6080
_exptl_absorpt_coefficient_mu    1.064
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 6.00cm
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            23211
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_sigmaI/netI    0.0372
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -54
_diffrn_reflns_limit_l_max       54
_diffrn_reflns_theta_min         1.52
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3980
_reflns_number_gt                3397
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker saint'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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. Due to disorder in the
dimethylformamide molecules of crystallisation, the routine SQUEEZE was
applied to the data. This dramatically improved the agreement indices.
;

_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^)+(0.1347P)^2^+525.0533P] 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    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3980
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0698
_refine_ls_wR_factor_ref         0.2274
_refine_ls_wR_factor_gt          0.2191
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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 1.0000 0.5000 1.0000 0.0382(3) Uani 1 2 d S . .
In2 In 1.1250 0.6250 1.013434(17) 0.0410(3) Uani 1 2 d S . .
C1 C 1.0309(5) 0.6134(4) 0.95769(19) 0.048(2) Uani 1 1 d . . .
C2 C 1.0283(5) 0.6444(5) 0.9278(2) 0.057(2) Uani 1 1 d . . .
C3 C 0.9935(7) 0.6140(6) 0.9055(2) 0.073(3) Uani 1 1 d . . .
H3 H 0.9718 0.5737 0.9086 0.087 Uiso 1 1 calc R . .
C4 C 1.0617(6) 0.7047(6) 0.9234(2) 0.071(3) Uani 1 1 d . . .
H4 H 1.0839 0.7260 0.9387 0.085 Uiso 1 1 calc R . .
C5 C 0.9910(8) 0.6429(8) 0.8786(3) 0.096(5) Uani 1 1 d . . .
H5 H 0.9659 0.6236 0.8637 0.115 Uiso 1 1 calc R . .
C6 C 1.0613(7) 0.7323(7) 0.8961(3) 0.095(5) Uani 1 1 d . . .
H6 H 1.0847 0.7716 0.8927 0.114 Uiso 1 1 calc R . .
C7 C 1.0269(7) 0.7021(8) 0.8742(3) 0.096(5) Uani 1 1 d . . .
C8 C 0.8244(8) 0.7349(8) 1.0853(3) 0.098(5) Uani 1 1 d . . .
C9 C 0.8895(9) 0.7547(9) 1.0870(4) 0.124(7) Uani 1 1 d . . .
H9 H 0.9007 0.7918 1.0979 0.149 Uiso 1 1 calc R . .
C10 C 0.8065(7) 0.6784(8) 1.0703(3) 0.096(4) Uani 1 1 d . . .
H10 H 0.7608 0.6636 1.0701 0.115 Uiso 1 1 calc R . .
C11 C 0.9423(7) 0.7196(6) 1.0725(3) 0.090(4) Uani 1 1 d . . .
H11 H 0.9882 0.7337 1.0734 0.108 Uiso 1 1 calc R . .
C12 C 0.8567(6) 0.6447(6) 1.0560(2) 0.069(3) Uani 1 1 d . . .
H12 H 0.8448 0.6077 1.0452 0.083 Uiso 1 1 calc R . .
C13 C 0.9244(6) 0.6641(5) 1.0572(2) 0.060(3) Uani 1 1 d . . .
C14 C 0.9796(5) 0.6267(4) 1.0404(2) 0.051(2) Uani 1 1 d . . .
O1 O 1.0086(4) 0.5557(3) 0.96034(13) 0.0563(17) Uani 1 1 d . . .
O2 O 1.0543(4) 0.6474(3) 0.97818(14) 0.0576(16) Uani 1 1 d . . .
O3 O 1.0196(6) 0.7296(7) 0.8471(2) 0.139(5) Uani 1 1 d . . .
O4 O 1.0414(4) 0.6446(3) 1.04350(14) 0.0579(17) Uani 1 1 d . . .
O5 O 0.9582(3) 0.5819(3) 1.02431(14) 0.0541(16) Uani 1 1 d . . .
O6 O 1.0998(3) 0.5256(3) 1.01301(13) 0.0496(14) 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 0.0469(5) 0.0311(4) 0.0367(5) -0.0022(3) 0.0081(3) -0.0145(3)
In2 0.0448(5) 0.0376(5) 0.0405(5) 0.000 0.000 -0.0161(3)
C1 0.050(5) 0.049(5) 0.046(5) 0.009(4) 0.002(4) -0.014(4)
C2 0.052(5) 0.067(6) 0.051(5) 0.020(4) -0.003(4) -0.023(5)
C3 0.093(8) 0.077(7) 0.048(6) 0.021(5) -0.005(5) -0.029(6)
C4 0.063(6) 0.076(7) 0.073(7) 0.028(6) -0.010(5) -0.029(5)
C5 0.111(11) 0.124(12) 0.054(7) 0.026(7) -0.006(7) -0.046(9)
C6 0.076(8) 0.100(9) 0.110(10) 0.062(8) -0.017(8) -0.044(7)
C7 0.089(9) 0.131(11) 0.069(7) 0.057(8) -0.012(7) -0.039(9)
C8 0.081(9) 0.138(12) 0.075(8) -0.063(8) -0.002(7) 0.028(9)
C9 0.115(13) 0.134(13) 0.125(13) -0.096(12) 0.006(10) 0.011(10)
C10 0.073(8) 0.144(13) 0.070(7) -0.039(8) 0.011(6) 0.013(8)
C11 0.082(8) 0.087(8) 0.102(9) -0.056(8) 0.013(7) -0.012(7)
C12 0.062(6) 0.077(7) 0.069(7) -0.026(6) 0.016(5) -0.010(5)
C13 0.070(6) 0.063(6) 0.049(5) -0.017(4) 0.010(5) -0.010(5)
C14 0.062(6) 0.046(5) 0.046(5) -0.004(4) 0.013(4) -0.005(4)
O1 0.076(4) 0.053(4) 0.041(3) 0.007(3) 0.002(3) -0.026(3)
O2 0.071(4) 0.049(3) 0.053(4) 0.006(3) -0.016(3) -0.014(3)
O3 0.114(8) 0.206(12) 0.097(7) 0.101(8) -0.028(6) -0.071(8)
O4 0.063(4) 0.060(4) 0.051(4) -0.016(3) 0.013(3) -0.018(3)
O5 0.052(4) 0.047(3) 0.064(4) -0.023(3) 0.013(3) -0.008(3)
O6 0.050(3) 0.038(3) 0.061(4) 0.003(3) 0.003(3) -0.016(3)

_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 O6 2.078(6) 17_767 ?
In1 O6 2.078(6) . ?
In1 O1 2.158(6) 17_767 ?
In1 O1 2.158(6) . ?
In1 O5 2.161(6) . ?
In1 O5 2.161(6) 17_767 ?
In2 O6 2.076(5) . ?
In2 O6 2.076(5) 14_655 ?
In2 O4 2.161(6) . ?
In2 O4 2.161(6) 14_655 ?
In2 O2 2.169(6) 14_655 ?
In2 O2 2.169(6) . ?
C1 O1 1.254(10) . ?
C1 O2 1.254(11) . ?
C1 C2 1.515(12) . ?
C2 C3 1.376(15) . ?
C2 C4 1.398(13) . ?
C3 C5 1.372(15) . ?
C4 C6 1.380(16) . ?
C5 C7 1.400(18) . ?
C6 C7 1.36(2) . ?
C7 O3 1.377(14) . ?
C8 C9 1.32(2) . ?
C8 C10 1.383(19) . ?
C8 O3 1.386(15) 31_566 ?
C9 C11 1.408(18) . ?
C10 C12 1.356(15) . ?
C11 C13 1.376(14) . ?
C12 C13 1.361(15) . ?
C13 C14 1.517(13) . ?
C14 O5 1.246(11) . ?
C14 O4 1.250(12) . ?
O3 C8 1.386(15) 23_665 ?

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
O6 In1 O6 179.997(1) 17_767 . ?
O6 In1 O1 92.5(2) 17_767 17_767 ?
O6 In1 O1 87.5(2) . 17_767 ?
O6 In1 O1 87.5(2) 17_767 . ?
O6 In1 O1 92.5(2) . . ?
O1 In1 O1 180.0(4) 17_767 . ?
O6 In1 O5 89.9(2) 17_767 . ?
O6 In1 O5 90.1(2) . . ?
O1 In1 O5 86.2(3) 17_767 . ?
O1 In1 O5 93.8(3) . . ?
O6 In1 O5 90.1(2) 17_767 17_767 ?
O6 In1 O5 89.9(2) . 17_767 ?
O1 In1 O5 93.8(3) 17_767 17_767 ?
O1 In1 O5 86.2(3) . 17_767 ?
O5 In1 O5 179.999(2) . 17_767 ?
O6 In2 O6 178.9(3) . 14_655 ?
O6 In2 O4 90.6(2) . . ?
O6 In2 O4 90.1(2) 14_655 . ?
O6 In2 O4 90.1(2) . 14_655 ?
O6 In2 O4 90.6(2) 14_655 14_655 ?
O4 In2 O4 100.1(4) . 14_655 ?
O6 In2 O2 86.3(2) . 14_655 ?
O6 In2 O2 92.9(2) 14_655 14_655 ?
O4 In2 O2 170.8(3) . 14_655 ?
O4 In2 O2 88.6(3) 14_655 14_655 ?
O6 In2 O2 92.9(2) . . ?
O6 In2 O2 86.3(2) 14_655 . ?
O4 In2 O2 88.6(3) . . ?
O4 In2 O2 170.8(3) 14_655 . ?
O2 In2 O2 82.8(4) 14_655 . ?
O1 C1 O2 124.3(8) . . ?
O1 C1 C2 117.7(8) . . ?
O2 C1 C2 118.0(8) . . ?
C3 C2 C4 120.5(9) . . ?
C3 C2 C1 120.7(8) . . ?
C4 C2 C1 118.7(9) . . ?
C5 C3 C2 120.1(10) . . ?
C6 C4 C2 119.0(11) . . ?
C3 C5 C7 118.9(12) . . ?
C7 C6 C4 120.2(10) . . ?
C6 C7 O3 123.0(12) . . ?
C6 C7 C5 121.2(10) . . ?
O3 C7 C5 115.6(13) . . ?
C9 C8 C10 121.3(12) . . ?
C9 C8 O3 122.7(13) . 31_566 ?
C10 C8 O3 116.0(14) . 31_566 ?
C8 C9 C11 120.1(12) . . ?
C12 C10 C8 119.0(13) . . ?
C13 C11 C9 118.6(12) . . ?
C10 C12 C13 121.1(11) . . ?
C12 C13 C11 119.7(10) . . ?
C12 C13 C14 120.4(9) . . ?
C11 C13 C14 119.8(10) . . ?
O5 C14 O4 126.5(9) . . ?
O5 C14 C13 115.9(9) . . ?
O4 C14 C13 117.6(8) . . ?
C1 O1 In1 126.8(6) . . ?
C1 O2 In2 132.5(6) . . ?
C7 O3 C8 119.4(11) . 23_665 ?
C14 O4 In2 125.5(6) . . ?
C14 O5 In1 138.5(6) . . ?
In2 O6 In1 117.5(3) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.808
_refine_diff_density_min         -0.577
_refine_diff_density_rms         0.311