# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1045476'
_audit_update_record             
;
2015-05-05 deposited with the CCDC.
2015-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H6 In N0 O8'
_chemical_formula_weight         441.03

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'
In In -0.7276 1.3100 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_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'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   20.305(5)
_cell_length_b                   10.022(3)
_cell_length_c                   17.220(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3504.2(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    0.836
_exptl_crystal_F_000             860
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.368
_exptl_crystal_size_mid          0.321
_exptl_crystal_size_min          0.268
_exptl_absorpt_coefficient_mu    0.694
_shelx_estimated_absorpt_T_min   0.784
_shelx_estimated_absorpt_T_max   0.836
_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      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12093
_diffrn_reflns_av_unetI/netI     0.0650
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.551
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.956
_reflns_number_total             3132
_reflns_number_gt                2139
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1220P)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         3132
_refine_ls_number_parameters     116
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0934
_refine_ls_R_factor_gt           0.0701
_refine_ls_wR_factor_ref         0.1876
_refine_ls_wR_factor_gt          0.1785
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_restrained_S_all      0.976
_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 0.36991(3) 0.2500 0.62654(3) 0.0292(3) Uani 1 2 d S T P . .
C1 C 0.3744(3) 0.4946(7) 0.5735(5) 0.0442(18) Uani 1 1 d . . . . .
C2 C 0.3766(3) 0.6315(6) 0.5350(4) 0.0294(14) Uani 1 1 d . . . . .
C3 C 0.3744(4) 0.7500 0.5764(5) 0.0239(18) Uani 1 2 d S T P . .
H3 H 0.3715 0.7500 0.6303 0.029 Uiso 1 2 calc R U P . .
C4 C 0.3820(3) 0.6313(5) 0.4539(3) 0.0237(12) Uiso 1 1 d . . . . .
H4 H 0.3832 0.5514 0.4265 0.028 Uiso 1 1 calc R U . . .
C5 C 0.3855(3) 0.7500 0.4161(4) 0.0125(15) Uiso 1 2 d S . P . .
C6 C 0.3849(6) 0.7500 0.3280(7) 0.053(3) Uiso 1 2 d S . P . .
C7 C 0.3268(4) 0.7500 0.2901(4) 0.0226(18) Uiso 1 2 d S . P . .
H7 H 0.2885 0.7500 0.3196 0.027 Uiso 1 2 calc R U P . .
C8 C 0.3207(4) 0.7500 0.2093(5) 0.027(2) Uani 1 2 d S T P . .
C9 C 0.3776(6) 0.7500 0.1636(9) 0.171(14) Uani 1 2 d S T P . .
H9 H 0.3740 0.7500 0.1097 0.206 Uiso 1 2 calc R U P . .
C10 C 0.4410(7) 0.7500 0.1987(7) 0.067(4) Uiso 1 2 d S . P . .
H10 H 0.4791 0.7500 0.1687 0.081 Uiso 1 2 calc R U P . .
C11 C 0.4441(4) 0.7500 0.2802(5) 0.034(2) Uani 1 2 d S T P . .
C13 C 0.2541(6) 0.7500 0.1757(7) 0.052(3) Uiso 1 2 d S . P . .
C14 C 0.5090(4) 0.7500 0.3150(5) 0.0275(19) Uani 1 2 d S T P . .
O1 O 0.3732(2) 0.4947(7) 0.6471(4) 0.0710(19) Uani 1 1 d . . . . .
O2 O 0.3686(2) 0.3970(4) 0.5331(3) 0.0502(14) Uani 1 1 d . . . . .
O3 O 0.2047(3) 0.7500 0.2173(4) 0.055(2) Uani 1 2 d S T P . .
O4 O 0.2471(3) 0.7500 0.1000(4) 0.063(2) Uani 1 2 d S T P . .
O5 O 0.5592(3) 0.7500 0.2708(4) 0.0307(14) Uani 1 2 d S T P . .
O6 O 0.5193(3) 0.7500 0.3877(4) 0.056(2) Uani 1 2 d S T 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 O3 2.177(7) 2_565 ?
In1 O2 2.182(5) 8_565 ?
In1 O2 2.182(5) . ?
In1 O6 2.263(6) 5_666 ?
In1 O5 2.280(6) 5_666 ?
In1 O4 2.420(7) 2_565 ?
In1 O1 2.479(7) 8_565 ?
In1 O1 2.479(7) . ?
In1 C1 2.617(7) 8_565 ?
In1 C1 2.617(7) . ?
In1 C13 2.656(11) 2_565 ?
In1 C14 2.657(8) 5_666 ?
C1 O2 1.205(9) . ?
C1 O1 1.267(10) . ?
C1 C2 1.525(8) . ?
C2 C3 1.386(8) . ?
C2 C4 1.401(8) . ?
C3 C2 1.386(8) 8_575 ?
C3 H3 0.9300 . ?
C4 C5 1.358(6) . ?
C4 H4 0.9300 . ?
C5 C4 1.358(6) 8_575 ?
C5 C6 1.518(13) . ?
C6 C7 1.348(13) . ?
C6 C11 1.457(14) . ?
C7 C8 1.398(12) . ?
C7 H7 0.9300 . ?
C8 C9 1.397(16) . ?
C8 C13 1.472(14) . ?
C9 C10 1.423(17) . ?
C9 H9 0.9300 . ?
C10 C11 1.405(14) . ?
C10 H10 0.9300 . ?
C11 C14 1.447(12) . ?
C13 O3 1.232(13) . ?
C13 O4 1.311(13) . ?
C13 In1 2.656(11) 2_564 ?
C14 O6 1.268(10) . ?
C14 O5 1.272(10) . ?
C14 In1 2.657(8) 5_666 ?
O3 In1 2.177(7) 2_564 ?
O4 In1 2.420(7) 2_564 ?
O5 In1 2.280(6) 5_666 ?
O6 In1 2.264(6) 5_666 ?

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 O2 121.38(18) 2_565 8_565 ?
O3 In1 O2 121.38(18) 2_565 . ?
O2 In1 O2 85.0(3) 8_565 . ?
O3 In1 O6 140.3(3) 2_565 5_666 ?
O2 In1 O6 86.14(17) 8_565 5_666 ?
O2 In1 O6 86.14(17) . 5_666 ?
O3 In1 O5 83.3(3) 2_565 5_666 ?
O2 In1 O5 125.42(14) 8_565 5_666 ?
O2 In1 O5 125.41(14) . 5_666 ?
O6 In1 O5 57.0(2) 5_666 5_666 ?
O3 In1 O4 56.8(2) 2_565 2_565 ?
O2 In1 O4 81.29(16) 8_565 2_565 ?
O2 In1 O4 81.29(16) . 2_565 ?
O6 In1 O4 162.9(2) 5_666 2_565 ?
O5 In1 O4 140.0(2) 5_666 2_565 ?
O3 In1 O1 85.19(13) 2_565 8_565 ?
O2 In1 O1 55.76(19) 8_565 8_565 ?
O2 In1 O1 140.7(2) . 8_565 ?
O6 In1 O1 89.36(12) 5_666 8_565 ?
O5 In1 O1 82.67(13) 5_666 8_565 ?
O4 In1 O1 93.05(12) 2_565 8_565 ?
O3 In1 O1 85.19(13) 2_565 . ?
O2 In1 O1 140.7(2) 8_565 . ?
O2 In1 O1 55.76(19) . . ?
O6 In1 O1 89.36(12) 5_666 . ?
O5 In1 O1 82.67(13) 5_666 . ?
O4 In1 O1 93.05(12) 2_565 . ?
O1 In1 O1 163.3(3) 8_565 . ?
O3 In1 C1 105.94(17) 2_565 8_565 ?
O2 In1 C1 27.2(2) 8_565 8_565 ?
O2 In1 C1 112.1(2) . 8_565 ?
O6 In1 C1 85.87(15) 5_666 8_565 ?
O5 In1 C1 104.41(17) 5_666 8_565 ?
O4 In1 C1 88.17(15) 2_565 8_565 ?
O1 In1 C1 28.6(2) 8_565 8_565 ?
O1 In1 C1 167.3(2) . 8_565 ?
O3 In1 C1 105.94(17) 2_565 . ?
O2 In1 C1 112.1(2) 8_565 . ?
O2 In1 C1 27.2(2) . . ?
O6 In1 C1 85.87(15) 5_666 . ?
O5 In1 C1 104.41(17) 5_666 . ?
O4 In1 C1 88.17(15) 2_565 . ?
O1 In1 C1 167.3(2) 8_565 . ?
O1 In1 C1 28.6(2) . . ?
C1 In1 C1 138.9(4) 8_565 . ?
O3 In1 C13 27.3(3) 2_565 2_565 ?
O2 In1 C13 102.9(2) 8_565 2_565 ?
O2 In1 C13 102.9(2) . 2_565 ?
O6 In1 C13 167.6(3) 5_666 2_565 ?
O5 In1 C13 110.6(3) 5_666 2_565 ?
O4 In1 C13 29.5(3) 2_565 2_565 ?
O1 In1 C13 88.85(12) 8_565 2_565 ?
O1 In1 C13 88.85(12) . 2_565 ?
C1 In1 C13 98.28(17) 8_565 2_565 ?
C1 In1 C13 98.27(16) . 2_565 ?
O3 In1 C14 111.9(3) 2_565 5_666 ?
O2 In1 C14 106.90(17) 8_565 5_666 ?
O2 In1 C14 106.90(18) . 5_666 ?
O6 In1 C14 28.5(2) 5_666 5_666 ?
O5 In1 C14 28.6(2) 5_666 5_666 ?
O4 In1 C14 168.6(2) 2_565 5_666 ?
O1 In1 C14 85.48(12) 8_565 5_666 ?
O1 In1 C14 85.48(12) . 5_666 ?
C1 In1 C14 95.75(16) 8_565 5_666 ?
C1 In1 C14 95.75(16) . 5_666 ?
C13 In1 C14 139.2(3) 2_565 5_666 ?
O2 C1 O1 125.2(7) . . ?
O2 C1 C2 118.8(7) . . ?
O1 C1 C2 115.7(7) . . ?
O2 C1 In1 55.8(3) . . ?
O1 C1 In1 69.6(4) . . ?
C2 C1 In1 174.7(6) . . ?
C3 C2 C4 121.1(5) . . ?
C3 C2 C1 123.1(6) . . ?
C4 C2 C1 115.7(6) . . ?
C2 C3 C2 117.9(7) 8_575 . ?
C2 C3 H3 121.0 8_575 . ?
C2 C3 H3 121.0 . . ?
C5 C4 C2 118.7(5) . . ?
C5 C4 H4 120.6 . . ?
C2 C4 H4 120.6 . . ?
C4 C5 C4 122.3(7) . 8_575 ?
C4 C5 C6 118.6(3) . . ?
C4 C5 C6 118.6(3) 8_575 . ?
C7 C6 C11 116.6(9) . . ?
C7 C6 C5 119.4(9) . . ?
C11 C6 C5 123.9(9) . . ?
C6 C7 C8 124.0(8) . . ?
C6 C7 H7 118.0 . . ?
C8 C7 H7 118.0 . . ?
C9 C8 C7 119.2(8) . . ?
C9 C8 C13 122.6(10) . . ?
C7 C8 C13 118.2(8) . . ?
C8 C9 C10 120.6(12) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C9 117.7(12) . . ?
C11 C10 H10 121.1 . . ?
C9 C10 H10 121.1 . . ?
C10 C11 C14 117.0(9) . . ?
C10 C11 C6 121.9(10) . . ?
C14 C11 C6 121.1(8) . . ?
O3 C13 O4 119.4(10) . . ?
O3 C13 C8 121.3(10) . . ?
O4 C13 C8 119.3(10) . . ?
O3 C13 In1 54.2(6) . 2_564 ?
O4 C13 In1 65.3(6) . 2_564 ?
C8 C13 In1 175.5(8) . 2_564 ?
O6 C14 O5 117.3(7) . . ?
O6 C14 C11 124.0(8) . . ?
O5 C14 C11 118.8(7) . . ?
O6 C14 In1 58.3(4) . 5_666 ?
O5 C14 In1 59.0(4) . 5_666 ?
C11 C14 In1 177.8(6) . 5_666 ?
C1 O1 In1 81.8(5) . . ?
C1 O2 In1 97.0(5) . . ?
C13 O3 In1 98.5(7) . 2_564 ?
C13 O4 In1 85.3(6) . 2_564 ?
C14 O5 In1 92.4(5) . 5_666 ?
C14 O6 In1 93.3(5) . 5_666 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 C3 171.2(6) . . . . ?
O1 C1 C2 C3 -3.0(9) . . . . ?
O2 C1 C2 C4 -9.6(8) . . . . ?
O1 C1 C2 C4 176.2(5) . . . . ?
C4 C2 C3 C2 1.1(11) . . . 8_575 ?
C1 C2 C3 C2 -179.8(4) . . . 8_575 ?
C3 C2 C4 C5 0.4(9) . . . . ?
C1 C2 C4 C5 -178.7(5) . . . . ?
C2 C4 C5 C4 -2.0(11) . . . 8_575 ?
C2 C4 C5 C6 -174.3(7) . . . . ?
C4 C5 C6 C7 86.3(6) . . . . ?
C4 C5 C6 C7 -86.3(6) 8_575 . . . ?
C4 C5 C6 C11 -93.7(6) . . . . ?
C4 C5 C6 C11 93.7(6) 8_575 . . . ?
C11 C6 C7 C8 0.000(1) . . . . ?
C5 C6 C7 C8 180.000(1) . . . . ?
C6 C7 C8 C9 0.000(1) . . . . ?
C6 C7 C8 C13 180.000(1) . . . . ?
C7 C8 C9 C10 0.000(1) . . . . ?
C13 C8 C9 C10 180.000(1) . . . . ?
C8 C9 C10 C11 0.000(1) . . . . ?
C9 C10 C11 C14 180.000(1) . . . . ?
C9 C10 C11 C6 0.000(1) . . . . ?
C7 C6 C11 C10 0.000(1) . . . . ?
C5 C6 C11 C10 180.000(1) . . . . ?
C7 C6 C11 C14 180.000(1) . . . . ?
C5 C6 C11 C14 0.000(1) . . . . ?
C9 C8 C13 O3 180.000(0) . . . . ?
C7 C8 C13 O3 0.000(1) . . . . ?
C9 C8 C13 O4 0.000(1) . . . . ?
C7 C8 C13 O4 180.000(1) . . . . ?
C10 C11 C14 O6 180.000(1) . . . . ?
C6 C11 C14 O6 0.000(1) . . . . ?
C10 C11 C14 O5 0.000(1) . . . . ?
C6 C11 C14 O5 180.000(1) . . . . ?
O2 C1 O1 In1 5.9(7) . . . . ?
C2 C1 O1 In1 179.7(5) . . . . ?
O1 C1 O2 In1 -6.7(8) . . . . ?
C2 C1 O2 In1 179.7(5) . . . . ?
O4 C13 O3 In1 0.000(0) . . . 2_564 ?
C8 C13 O3 In1 180.000(0) . . . 2_564 ?
O3 C13 O4 In1 0.000(1) . . . 2_564 ?
C8 C13 O4 In1 180.000(0) . . . 2_564 ?
O6 C14 O5 In1 0.000(1) . . . 5_666 ?
C11 C14 O5 In1 180.000(0) . . . 5_666 ?
O5 C14 O6 In1 0.000(1) . . . 5_666 ?
C11 C14 O6 In1 180.000(1) . . . 5_666 ?

_refine_diff_density_max         1.569
_refine_diff_density_min         -2.694
_refine_diff_density_rms         0.153

# 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 0.306 -0.013 -0.027 2282 1499 ' '
_platon_squeeze_details          
;
;


#End of Crystallographic Information File 
