# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_InOF-15
_database_code_depnum_ccdc_archive 'CCDC 1554960'
_audit_update_record             
;
2017-06-08 deposited with the CCDC.
2017-10-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        InOF-15
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10.50 H6.50 In0.50 N O2.67'
_chemical_formula_weight         246.74

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           hexagonal
_symmetry_space_group_name_H-M   P63/m

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

_cell_length_a                   15.1951(11)
_cell_length_b                   15.1951(11)
_cell_length_c                   23.091(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     4617.2(7)
_cell_formula_units_Z            12
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6405
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      28.15

_exptl_crystal_description       'light yellow'
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.065
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1468
_exptl_absorpt_coefficient_mu    0.792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9690
_exptl_absorpt_correction_T_max  0.9766
_exptl_absorpt_process_details   'Inorg. Chem., 2015, 54, 8375-8379'

_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  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27530
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_sigmaI/netI    0.0410
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         28.24
_reflns_number_total             3912
_reflns_number_gt                3104
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0817P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3912
_refine_ls_number_parameters     135
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1330
_refine_ls_wR_factor_gt          0.1277
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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 -0.023 -0.018 0.250 1189.3 -26.7
2 -0.025 -0.024 0.750 1189.2 -22.7
_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 0.20943(2) 0.52396(2) 0.7500 0.03452(13) Uani 1 2 d S . .
N1 N -0.0265(3) 0.6013(2) 0.50539(13) 0.0555(8) Uani 1 1 d . . .
O1 O 0.1322(2) 0.5607(2) 0.68366(11) 0.0574(7) Uani 1 1 d . . .
C10 C 0.1426(3) 0.6419(3) 0.66314(14) 0.0465(8) Uani 1 1 d . . .
C3 C 0.0826(3) 0.6318(3) 0.60914(14) 0.0464(8) Uani 1 1 d . . .
C8 C -0.0101(3) 0.6797(3) 0.54252(16) 0.0511(9) Uani 1 1 d . . .
C9 C 0.0447(3) 0.6993(3) 0.59506(16) 0.0483(8) Uani 1 1 d . . .
C2 C 0.0622(3) 0.5538(3) 0.57266(16) 0.0533(9) Uani 1 1 d . . .
H2 H 0.0835 0.5078 0.5821 0.064 Uiso 1 1 calc R . .
C1 C 0.0089(3) 0.5418(3) 0.52053(16) 0.0522(9) Uani 1 1 d . . .
C7 C -0.0516(3) 0.7408(3) 0.52639(19) 0.0588(10) Uani 1 1 d . . .
H7 H -0.0876 0.7280 0.4919 0.071 Uiso 1 1 calc R . .
C4 C 0.0563(3) 0.7807(3) 0.62987(17) 0.0586(10) Uani 1 1 d . . .
H4 H 0.0929 0.7958 0.6643 0.070 Uiso 1 1 calc R . .
C6 C -0.0389(3) 0.8195(3) 0.5616(2) 0.0660(11) Uani 1 1 d . . .
H6 H -0.0657 0.8603 0.5507 0.079 Uiso 1 1 calc R . .
C5 C 0.0134(3) 0.8376(4) 0.6129(2) 0.0699(12) Uani 1 1 d . . .
H5 H 0.0200 0.8899 0.6368 0.084 Uiso 1 1 calc R . .
O3 O 0.3333 0.6667 0.7500 0.0383(11) Uani 1 6 d S . .
O2 O 0.2002(2) 0.7290(2) 0.68210(11) 0.0580(7) Uani 1 1 d . . .
O4 O 0.0850(3) 0.3757(3) 0.7500 0.0959(14) Uani 1 2 d S . .
C11 C 0.0129(5) 0.3113(5) 0.7500 0.0959(14) Uani 1 2 d S . .
H11A H 0.0122 0.2614 0.7242 0.144 Uiso 0.50 1 calc PR . .
H11B H -0.0362 0.3294 0.7374 0.144 Uiso 0.50 1 calc PR . .
H11C H -0.0037 0.2837 0.7884 0.144 Uiso 0.50 1 calc PR . .

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 0.0432(2) 0.04219(19) 0.01708(18) 0.000 0.000 0.02053(14)
N1 0.0718(19) 0.0665(19) 0.0385(17) -0.0099(14) -0.0233(15) 0.0423(17)
O1 0.0663(16) 0.0642(16) 0.0396(14) 0.0023(12) -0.0206(12) 0.0310(13)
C10 0.057(2) 0.063(2) 0.0246(15) -0.0047(15) -0.0085(15) 0.0340(18)
C3 0.0547(19) 0.062(2) 0.0280(16) -0.0024(15) -0.0111(15) 0.0329(17)
C8 0.058(2) 0.063(2) 0.0394(19) -0.0011(17) -0.0115(16) 0.0352(18)
C9 0.0511(19) 0.058(2) 0.0373(18) -0.0022(16) -0.0083(15) 0.0284(17)
C2 0.075(2) 0.066(2) 0.0336(18) -0.0092(17) -0.0219(18) 0.046(2)
C1 0.065(2) 0.065(2) 0.0345(17) -0.0072(16) -0.0195(17) 0.0383(19)
C7 0.063(2) 0.066(2) 0.057(2) 0.001(2) -0.0164(19) 0.038(2)
C4 0.066(2) 0.070(2) 0.046(2) -0.0136(19) -0.0136(19) 0.038(2)
C6 0.071(3) 0.072(3) 0.068(3) 0.000(2) -0.012(2) 0.046(2)
C5 0.080(3) 0.073(3) 0.072(3) -0.011(2) -0.009(2) 0.049(2)
O3 0.0413(17) 0.0413(17) 0.032(3) 0.000 0.000 0.0207(8)
O2 0.0686(16) 0.0635(16) 0.0459(15) -0.0116(13) -0.0279(13) 0.0360(13)
O4 0.060(2) 0.0450(18) 0.147(4) 0.000 0.000 -0.0004(14)
C11 0.060(2) 0.0450(18) 0.147(4) 0.000 0.000 -0.0004(14)

_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 2.0407(3) . ?
In1 O4 2.095(4) . ?
In1 O1 2.166(2) . ?
In1 O1 2.166(2) 10_557 ?
In1 O2 2.174(2) 12_667 ?
In1 O2 2.174(2) 3_665 ?
N1 C1 1.308(5) . ?
N1 C8 1.385(5) . ?
O1 C10 1.256(4) . ?
C10 O2 1.245(4) . ?
C10 C3 1.506(4) . ?
C3 C2 1.358(5) . ?
C3 C9 1.443(5) . ?
C8 C7 1.409(5) . ?
C8 C9 1.416(5) . ?
C9 C4 1.410(5) . ?
C2 C1 1.411(5) . ?
C2 H2 0.9300 . ?
C1 C1 1.498(8) 7_566 ?
C7 C6 1.378(6) . ?
C7 H7 0.9300 . ?
C4 C5 1.376(6) . ?
C4 H4 0.9300 . ?
C6 C5 1.375(6) . ?
C6 H6 0.9300 . ?
C5 H5 0.9300 . ?
O3 In1 2.0407(3) 8_567 ?
O3 In1 2.0407(3) 3_665 ?
O2 In1 2.174(2) 8_567 ?
O4 C11 1.042(7) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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 178.37(14) . . ?
O3 In1 O1 93.27(7) . . ?
O4 In1 O1 87.88(13) . . ?
O3 In1 O1 93.27(7) . 10_557 ?
O4 In1 O1 87.88(13) . 10_557 ?
O1 In1 O1 90.01(15) . 10_557 ?
O3 In1 O2 93.08(7) . 12_667 ?
O4 In1 O2 85.79(12) . 12_667 ?
O1 In1 O2 173.55(10) . 12_667 ?
O1 In1 O2 88.49(11) 10_557 12_667 ?
O3 In1 O2 93.08(7) . 3_665 ?
O4 In1 O2 85.79(12) . 3_665 ?
O1 In1 O2 88.49(11) . 3_665 ?
O1 In1 O2 173.55(10) 10_557 3_665 ?
O2 In1 O2 92.30(16) 12_667 3_665 ?
C1 N1 C8 118.0(3) . . ?
C10 O1 In1 134.6(2) . . ?
O2 C10 O1 126.0(3) . . ?
O2 C10 C3 117.9(3) . . ?
O1 C10 C3 116.0(3) . . ?
C2 C3 C9 118.9(3) . . ?
C2 C3 C10 117.7(3) . . ?
C9 C3 C10 123.4(3) . . ?
N1 C8 C7 117.1(3) . . ?
N1 C8 C9 123.0(3) . . ?
C7 C8 C9 119.9(4) . . ?
C4 C9 C8 118.4(3) . . ?
C4 C9 C3 125.1(3) . . ?
C8 C9 C3 116.4(3) . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
N1 C1 C2 123.1(4) . . ?
N1 C1 C1 117.1(4) . 7_566 ?
C2 C1 C1 119.8(4) . 7_566 ?
C6 C7 C8 120.1(4) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C5 C4 C9 119.9(4) . . ?
C5 C4 H4 120.1 . . ?
C9 C4 H4 120.1 . . ?
C5 C6 C7 119.9(4) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C6 C5 C4 121.9(4) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
In1 O3 In1 120.0 8_567 . ?
In1 O3 In1 120.0 8_567 3_665 ?
In1 O3 In1 120.0 . 3_665 ?
C10 O2 In1 134.1(2) . 8_567 ?
C11 O4 In1 165.9(6) . . ?
O4 C11 H11A 109.5 . . ?
O4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.24
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.869
_refine_diff_density_min         -1.755
_refine_diff_density_rms         0.138
_exptl_crystal_recrystallization_method 'Vapour deposition'
