# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1535494'
_audit_update_record             
;
2017-03-01 deposited with the CCDC.
2018-12-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            MIL53(In)_OH
_chemical_melting_point          'not measured'
_chemical_formula_moiety         'C8 H4 In O8'
_chemical_formula_sum            'C8 H4 In O8'
_chemical_formula_weight         342.93

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   Cmca

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

_cell_length_a                   37.4012(11)
_cell_length_b                   23.0052(7)
_cell_length_c                   7.1553(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     6156.6(3)
_cell_formula_units_Z            16
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9034
_cell_measurement_theta_min      3.3531
_cell_measurement_theta_max      28.3152

_exptl_crystal_description       block
_exptl_crystal_colour            transparent
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2640
_exptl_absorpt_coefficient_mu    1.555
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.633
_exptl_absorpt_correction_T_max  0.792
_exptl_absorpt_process_details   SADAB

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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 9.00cm
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            15786
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.09
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2773
_reflns_number_gt                2616
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.1045P)²+12.2290P] 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     SHELXL
_refine_ls_extinction_coef       0.00011(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2773
_refine_ls_number_parameters     169
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.1412
_refine_ls_wR_factor_gt          0.1388
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.139
_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
In1 In 0.0000 0.245232(18) 0.95804(8) 0.0185(2) Uani 1 2 d S . .
In2 In 0.247179(11) 0.5000 1.0000 0.0184(2) Uani 1 2 d S . .
O1 O 0.20566(9) 0.44316(16) 0.9021(4) 0.0410(9) Uani 1 1 d . . .
O2 O 0.20946(9) 0.44341(16) 0.5918(4) 0.0422(9) Uani 1 1 d . . .
O3 O 0.04149(9) 0.30444(16) 0.8614(5) 0.0446(9) Uani 1 1 d . . .
O4 O 0.04282(9) 0.30946(17) 0.5522(5) 0.0424(9) Uani 1 1 d . . .
O5 O 0.09352(13) 0.3461(3) 1.0609(6) 0.0790(17) Uani 1 1 d U . .
H5 H 0.0741 0.3303 1.0441 0.118 Uiso 1 1 calc R . .
O6 O 0.15714(13) 0.4034(3) 0.3928(6) 0.0821(17) Uani 1 1 d U . .
H6 H 0.1766 0.4187 0.4104 0.123 Uiso 1 1 calc R . .
O7 O 0.2500 0.45533(17) 1.2500 0.0287(9) Uani 1 2 d S . .
O8 O 0.0000 0.29424(17) 1.2008(6) 0.0273(9) Uani 1 2 d S . .
O9 O 0.2500 0.3400(5) 0.2500 0.199(6) Uani 1 2 d SU . .
O10 O 0.0000 0.4098(6) 0.182(2) 0.213(7) Uani 1 2 d SU . .
C1 C 0.19371(11) 0.4320(2) 0.7441(7) 0.0321(10) Uani 1 1 d . . .
C2 C 0.15831(12) 0.4023(2) 0.7314(7) 0.0343(11) Uani 1 1 d . . .
C3 C 0.14077(15) 0.3871(3) 0.8964(7) 0.0417(13) Uani 1 1 d . . .
C4 C 0.10819(15) 0.3602(3) 0.8929(7) 0.0443(14) Uani 1 1 d . . .
C5 C 0.09163(12) 0.3478(2) 0.7207(7) 0.0344(11) Uani 1 1 d . . .
C6 C 0.10902(16) 0.3632(3) 0.5576(8) 0.0458(15) Uani 1 1 d . . .
C7 C 0.14208(16) 0.3896(3) 0.5603(7) 0.0462(16) Uani 1 1 d . . .
C8 C 0.05624(12) 0.3183(2) 0.7095(6) 0.0309(10) Uani 1 1 d . . .
H1 H 0.1519(16) 0.399(2) 1.006(8) 0.033(16) Uiso 1 1 d . . .
H2 H 0.0984(19) 0.355(3) 0.464(10) 0.06(2) Uiso 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 0.0133(3) 0.0279(3) 0.0144(3) 0.00193(14) 0.000 0.000
In2 0.0136(3) 0.0277(3) 0.0140(3) -0.00166(13) 0.000 0.000
O1 0.0370(19) 0.061(2) 0.0249(17) 0.0017(16) -0.0072(15) -0.0272(17)
O2 0.037(2) 0.064(2) 0.0260(17) -0.0040(16) 0.0073(15) -0.0261(17)
O3 0.0396(19) 0.065(2) 0.0294(18) -0.0047(16) 0.0077(15) -0.0313(17)
O4 0.035(2) 0.063(2) 0.0298(18) 0.0017(16) -0.0048(15) -0.0268(17)
O5 0.068(3) 0.144(4) 0.025(2) 0.002(2) 0.003(2) -0.070(3)
O6 0.068(3) 0.157(5) 0.022(2) 0.001(2) 0.004(2) -0.069(3)
O7 0.044(2) 0.028(2) 0.015(2) 0.000 -0.0014(19) 0.000
O8 0.033(2) 0.033(2) 0.017(2) -0.0004(17) 0.000 0.000
O9 0.322(15) 0.096(7) 0.177(12) 0.000 0.007(11) 0.000
O10 0.324(16) 0.105(8) 0.211(13) 0.000(9) 0.000 0.000
C1 0.028(2) 0.041(2) 0.027(2) 0.000(2) -0.001(2) -0.0087(18)
C2 0.030(2) 0.048(3) 0.025(2) -0.001(2) 0.001(2) -0.016(2)
C3 0.036(3) 0.068(4) 0.021(3) 0.000(2) -0.004(2) -0.024(3)
C4 0.040(3) 0.070(4) 0.023(3) 0.000(2) 0.001(2) -0.028(3)
C5 0.031(2) 0.046(3) 0.026(2) -0.002(2) 0.0028(19) -0.017(2)
C6 0.039(3) 0.077(4) 0.021(3) 0.000(2) -0.005(2) -0.029(3)
C7 0.040(3) 0.080(4) 0.019(2) -0.002(2) 0.002(2) -0.034(3)
C8 0.028(2) 0.043(2) 0.022(2) -0.002(2) -0.0012(18) -0.0121(19)

_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 O8 2.052(4) 2_554 ?
In1 O8 2.071(4) . ?
In1 O4 2.145(3) 2 ?
In1 O4 2.145(3) 11_566 ?
In1 O3 2.177(3) . ?
In1 O3 2.178(3) 12 ?
In2 O7 2.0657(19) . ?
In2 O7 2.0658(19) 6_554 ?
In2 O1 2.147(3) 4_567 ?
In2 O1 2.148(3) . ?
In2 O2 2.181(3) 6 ?
In2 O2 2.181(3) 7_546 ?
O1 C1 1.242(6) . ?
O2 C1 1.267(6) . ?
O2 In2 2.181(3) 6_554 ?
O3 C8 1.259(5) . ?
O4 C8 1.249(5) . ?
O4 In1 2.145(3) 2_554 ?
O5 C4 1.361(7) . ?
O5 H5 0.8200 . ?
O6 C7 1.362(7) . ?
O6 H6 0.8200 . ?
O7 In2 2.0657(19) 6 ?
O8 In1 2.052(4) 2 ?
C1 C2 1.493(6) . ?
C2 C3 1.395(7) . ?
C2 C7 1.397(7) . ?
C3 C4 1.367(8) . ?
C3 H1 0.93(6) . ?
C4 C5 1.409(7) . ?
C5 C6 1.383(7) . ?
C5 C8 1.490(6) . ?
C6 C7 1.377(8) . ?
C6 H2 0.80(7) . ?

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
O8 In1 O8 173.28(11) 2_554 . ?
O8 In1 O4 91.27(12) 2_554 2 ?
O8 In1 O4 93.20(12) . 2 ?
O8 In1 O4 91.27(12) 2_554 11_566 ?
O8 In1 O4 93.20(12) . 11_566 ?
O4 In1 O4 96.6(2) 2 11_566 ?
O8 In1 O3 89.54(12) 2_554 . ?
O8 In1 O3 85.75(12) . . ?
O4 In1 O3 177.02(16) 2 . ?
O4 In1 O3 86.25(15) 11_566 . ?
O8 In1 O3 89.54(12) 2_554 12 ?
O8 In1 O3 85.75(12) . 12 ?
O4 In1 O3 86.25(15) 2 12 ?
O4 In1 O3 177.02(16) 11_566 12 ?
O3 In1 O3 90.9(2) . 12 ?
O7 In2 O7 174.14(2) . 6_554 ?
O7 In2 O1 93.30(11) . 4_567 ?
O7 In2 O1 90.94(11) 6_554 4_567 ?
O7 In2 O1 90.94(11) . . ?
O7 In2 O1 93.30(11) 6_554 . ?
O1 In2 O1 87.4(2) 4_567 . ?
O7 In2 O2 89.90(11) . 6 ?
O7 In2 O2 85.75(11) 6_554 6 ?
O1 In2 O2 94.36(14) 4_567 6 ?
O1 In2 O2 178.02(14) . 6 ?
O7 In2 O2 85.75(11) . 7_546 ?
O7 In2 O2 89.90(11) 6_554 7_546 ?
O1 In2 O2 178.02(14) 4_567 7_546 ?
O1 In2 O2 94.36(14) . 7_546 ?
O2 In2 O2 83.9(2) 6 7_546 ?
C1 O1 In2 133.0(3) . . ?
C1 O2 In2 136.8(3) . 6_554 ?
C8 O3 In1 138.1(3) . . ?
C8 O4 In1 132.7(3) . 2_554 ?
C4 O5 H5 109.5 . . ?
C7 O6 H6 109.5 . . ?
In2 O7 In2 120.33(19) 6 . ?
In1 O8 In1 120.76(19) 2 . ?
O1 C1 O2 125.0(4) . . ?
O1 C1 C2 118.0(4) . . ?
O2 C1 C2 117.0(4) . . ?
C3 C2 C7 119.0(4) . . ?
C3 C2 C1 118.7(4) . . ?
C7 C2 C1 122.3(4) . . ?
C4 C3 C2 121.1(5) . . ?
C4 C3 H1 123(4) . . ?
C2 C3 H1 115(4) . . ?
O5 C4 C3 116.9(5) . . ?
O5 C4 C5 123.1(5) . . ?
C3 C4 C5 120.0(5) . . ?
C6 C5 C4 118.6(4) . . ?
C6 C5 C8 119.3(4) . . ?
C4 C5 C8 122.0(4) . . ?
C7 C6 C5 121.6(5) . . ?
C7 C6 H2 124(5) . . ?
C5 C6 H2 115(5) . . ?
O6 C7 C6 117.5(5) . . ?
O6 C7 C2 122.8(5) . . ?
C6 C7 C2 119.7(5) . . ?
O4 C8 O3 124.1(4) . . ?
O4 C8 C5 118.6(4) . . ?
O3 C8 C5 117.3(4) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.988
_refine_diff_density_min         -0.584
_refine_diff_density_rms         0.180
####################################################################### 
# 
# 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_imma2
_database_code_depnum_ccdc_archive 'CCDC 1535495'
_audit_update_record             
;
2017-03-01 deposited with the CCDC.
2018-12-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            MIL53(In)_Br
_chemical_melting_point          'not measured'
_chemical_formula_moiety         'C8 Br In O5'
_chemical_formula_sum            'C8 Br In O5'
_chemical_formula_weight         370.81

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'
Br Br -0.2901 2.4595 '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   Imma

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

_cell_length_a                   17.4254(9)
_cell_length_b                   7.2516(3)
_cell_length_c                   13.3713(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1689.62(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3171
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      28.27

_exptl_crystal_description       block
_exptl_crystal_colour            transparent
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    3.760
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.513
_exptl_absorpt_correction_T_max  0.661
_exptl_absorpt_process_details   SADAB

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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 9.00cm
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            4260
_diffrn_reflns_av_R_equivalents  0.0902
_diffrn_reflns_av_sigmaI/netI    0.0428
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         24.99
_reflns_number_total             839
_reflns_number_gt                664
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0837P)²+4.2700P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   none
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0020(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         839
_refine_ls_number_parameters     67
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1235
_refine_ls_wR_factor_gt          0.1183
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.105
_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 0.5000 0.0000 0.5000 0.02103(9) Uani 1 4 d S . .
O1 O 0.41095(10) 0.0975(2) 0.40067(15) 0.0594(5) Uani 1 1 d . . .
O2 O 0.5000 0.2500 0.5759(2) 0.0298(7) Uani 1 4 d S . .
Br1 Br 0.26552(17) -0.1123(4) 0.4075(2) 0.0942(8) Uani 0.13 1 d P . .
Br2 Br 0.2891(2) -0.1424(4) 0.3645(3) 0.0955(10) Uani 0.13 1 d PU . .
C1 C 0.38488(19) 0.2500 0.3762(3) 0.0392(9) Uani 1 2 d S . .
C2 C 0.3141(2) 0.2500 0.3131(3) 0.0498(10) Uani 1 2 d S . .
C3 C 0.2684(3) 0.0953(7) 0.3023(5) 0.0632(16) Uani 0.50 1 d P . .
C4 C 0.2992(3) 0.1003(8) 0.2479(5) 0.0630(16) Uani 0.50 1 d P . .

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 0.01968(16) 0.01246(15) 0.03096(17) 0.00217(9) 0.000 0.000
O1 0.0622(10) 0.0303(8) 0.0859(12) -0.0053(9) -0.0438(9) 0.0094(9)
O2 0.0412(15) 0.0157(12) 0.0326(14) 0.000 0.000 0.000
Br1 0.0934(16) 0.0766(13) 0.1125(17) 0.0602(12) -0.0579(14) -0.0416(13)
Br2 0.1059(19) 0.0504(14) 0.130(2) 0.0254(15) -0.0616(17) -0.0147(15)
C1 0.0326(15) 0.0266(14) 0.058(2) 0.000 -0.0167(15) 0.000
C2 0.0492(18) 0.0141(13) 0.086(3) 0.000 -0.0352(18) 0.000
C3 0.066(3) 0.022(2) 0.102(4) 0.022(2) -0.050(3) 0.001(2)
C4 0.054(3) 0.039(3) 0.096(4) -0.020(3) -0.046(3) 0.008(2)

_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 O2 2.0778(15) . ?
In1 O2 2.0779(15) 9_656 ?
In1 O1 2.1614(18) . ?
In1 O1 2.1614(18) 12_655 ?
In1 O1 2.1615(18) 9_656 ?
In1 O1 2.1615(18) 4_556 ?
O1 C1 1.240(2) . ?
O2 In1 2.0778(15) 2_655 ?
Br1 Br2 0.739(5) . ?
Br1 Br2 1.914(4) 11 ?
Br1 Br1 1.998(6) 11 ?
Br1 C3 2.060(6) . ?
Br2 Br2 1.560(6) 11 ?
Br2 Br1 1.914(4) 11 ?
Br2 C3 1.948(6) . ?
Br2 C4 2.358(7) . ?
C1 O1 1.240(2) 11_565 ?
C1 C2 1.495(5) . ?
C2 C3 1.383(6) 11_565 ?
C2 C3 1.383(6) . ?
C2 C4 1.416(6) 11_565 ?
C2 C4 1.416(6) . ?
C3 C4 0.904(9) . ?
C3 C4 1.357(8) 7_545 ?
C3 C3 1.539(12) 7_545 ?
C4 C3 1.357(8) 7_545 ?
C4 C4 1.715(11) 7_545 ?

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
O2 In1 O2 180.0 . 9_656 ?
O2 In1 O1 90.85(7) . . ?
O2 In1 O1 89.15(7) 9_656 . ?
O2 In1 O1 90.85(7) . 12_655 ?
O2 In1 O1 89.15(7) 9_656 12_655 ?
O1 In1 O1 91.77(10) . 12_655 ?
O2 In1 O1 89.15(7) . 9_656 ?
O2 In1 O1 90.85(7) 9_656 9_656 ?
O1 In1 O1 180.0 . 9_656 ?
O1 In1 O1 88.23(10) 12_655 9_656 ?
O2 In1 O1 89.15(7) . 4_556 ?
O2 In1 O1 90.85(7) 9_656 4_556 ?
O1 In1 O1 88.23(10) . 4_556 ?
O1 In1 O1 180.0 12_655 4_556 ?
O1 In1 O1 91.77(10) 9_656 4_556 ?
C1 O1 In1 135.83(18) . . ?
In1 O2 In1 121.50(15) 2_655 . ?
Br2 Br1 Br2 51.2(3) . 11 ?
Br2 Br1 Br1 72.8(3) . 11 ?
Br2 Br1 Br1 21.66(14) 11 11 ?
Br2 Br1 C3 70.9(4) . . ?
Br2 Br1 C3 118.0(3) 11 . ?
Br1 Br1 C3 136.94(19) 11 . ?
Br1 Br2 Br2 107.2(3) . 11 ?
Br1 Br2 Br1 85.5(4) . 11 ?
Br2 Br2 Br1 21.66(15) 11 11 ?
Br1 Br2 C3 88.1(4) . . ?
Br2 Br2 C3 152.3(2) 11 . ?
Br1 Br2 C3 155.6(3) 11 . ?
Br1 Br2 C4 109.5(4) . . ?
Br2 Br2 C4 138.30(17) 11 . ?
Br1 Br2 C4 155.3(3) 11 . ?
C3 Br2 C4 21.7(2) . . ?
O1 C1 O1 126.3(3) 11_565 . ?
O1 C1 C2 116.85(16) 11_565 . ?
O1 C1 C2 116.85(16) . . ?
C3 C2 C3 108.4(5) 11_565 . ?
C3 C2 C4 37.7(4) 11_565 11_565 ?
C3 C2 C4 116.9(4) . 11_565 ?
C3 C2 C4 116.9(4) 11_565 . ?
C3 C2 C4 37.7(4) . . ?
C4 C2 C4 100.1(6) 11_565 . ?
C3 C2 C1 122.3(3) 11_565 . ?
C3 C2 C1 122.3(3) . . ?
C4 C2 C1 119.9(3) 11_565 . ?
C4 C2 C1 119.9(3) . . ?
C4 C3 C4 96.7(7) . 7_545 ?
C4 C3 C2 73.1(5) . . ?
C4 C3 C2 122.0(5) 7_545 . ?
C4 C3 C3 61.1(6) . 7_545 ?
C4 C3 C3 35.7(4) 7_545 7_545 ?
C2 C3 C3 109.5(4) . 7_545 ?
C4 C3 Br2 105.6(6) . . ?
C4 C3 Br2 113.3(4) 7_545 . ?
C2 C3 Br2 124.5(4) . . ?
C3 C3 Br2 117.7(2) 7_545 . ?
C4 C3 Br1 126.3(6) . . ?
C4 C3 Br1 109.7(4) 7_545 . ?
C2 C3 Br1 122.4(4) . . ?
C3 C3 Br1 127.6(3) 7_545 . ?
Br2 C3 Br1 21.02(15) . . ?
C3 C4 C3 83.2(7) . 7_545 ?
C3 C4 C2 69.2(5) . . ?
C3 C4 C2 119.0(5) 7_545 . ?
C3 C4 C4 51.8(5) . 7_545 ?
C3 C4 C4 31.6(4) 7_545 7_545 ?
C2 C4 C4 99.4(4) . 7_545 ?
C3 C4 Br2 52.7(5) . . ?
C3 C4 Br2 104.0(4) 7_545 . ?
C2 C4 Br2 100.3(4) . . ?
C4 C4 Br2 84.5(3) 7_545 . ?

_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.964
_refine_diff_density_max         1.844
_refine_diff_density_min         -0.648
_refine_diff_density_rms         0.148
####################################################################### 
# 
# 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_imma
_database_code_depnum_ccdc_archive 'CCDC 1535496'
_audit_update_record             
;
2017-03-01 deposited with the CCDC.
2018-12-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            MIL53(In)_NO2
_chemical_melting_point          'not measured'
_chemical_formula_moiety         'C8 In N O9'
_chemical_formula_sum            'C8 In N O9'
_chemical_formula_weight         368.91

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   Imma

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

_cell_length_a                   18.6290(9)
_cell_length_b                   7.3019(4)
_cell_length_c                   11.4527(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1557.88(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2878
_cell_measurement_theta_min      2.1865
_cell_measurement_theta_max      28.3415

_exptl_crystal_description       block
_exptl_crystal_colour            transparent
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    1.549
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.757
_exptl_absorpt_correction_T_max  0.857
_exptl_absorpt_process_details   SADAB

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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 9.00cm
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            4096
_diffrn_reflns_av_R_equivalents  0.0921
_diffrn_reflns_av_sigmaI/netI    0.0485
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         25.00
_reflns_number_total             777
_reflns_number_gt                612
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.1237P)²+0.1246P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   none
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0059(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         777
_refine_ls_number_parameters     73
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.1566
_refine_ls_wR_factor_gt          0.1493
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.059
_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
In1 In 0.5000 0.0000 0.5000 0.0186(5) Uani 1 4 d S . .
N1 N 0.3066(13) -0.080(4) 0.693(2) 0.060(7) Uani 0.25 1 d PDU . .
O1 O 0.41577(18) 0.0974(4) 0.6134(3) 0.0482(11) Uani 1 1 d . . .
O2 O 0.5000 0.2500 0.4129(5) 0.0290(15) Uani 1 4 d S . .
O3 O 0.2910(14) -0.148(4) 0.595(2) 0.111(8) Uani 0.25 1 d PU . .
O4 O 0.3444(11) -0.160(3) 0.772(2) 0.098(7) Uani 0.25 1 d PD . .
O5 O 0.0491(13) 0.2500 0.3200(12) 0.245(8) Uani 1 2 d SU . .
C1 C 0.2828(4) 0.0885(9) 0.7212(8) 0.063(2) Uani 1 1 d . . .
C2 C 0.3170(4) 0.2500 0.6953(8) 0.041(2) Uani 1 2 d S . .
C3 C 0.3888(4) 0.2500 0.6340(7) 0.0359(17) Uani 1 2 d S . .

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 0.0138(6) 0.0120(6) 0.0300(7) -0.00134(18) 0.000 0.000
N1 0.056(13) 0.060(13) 0.065(13) -0.006(12) 0.039(11) -0.009(11)
O1 0.043(2) 0.0314(19) 0.070(3) 0.0061(18) 0.0334(18) 0.0091(15)
O2 0.035(3) 0.015(3) 0.037(4) 0.000 0.000 0.000
O3 0.118(14) 0.094(13) 0.121(14) -0.039(12) 0.042(12) -0.006(11)
O4 0.068(14) 0.079(13) 0.15(2) 0.034(16) 0.033(15) 0.023(11)
O5 0.310(17) 0.225(15) 0.202(11) 0.000 -0.084(12) 0.000
C1 0.053(4) 0.027(3) 0.108(6) -0.001(3) 0.046(4) 0.000(3)
C2 0.036(4) 0.021(4) 0.067(6) 0.000 0.026(4) 0.000
C3 0.032(4) 0.024(3) 0.051(5) 0.000 0.015(3) 0.000

_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 O2 2.080(3) . ?
In1 O2 2.080(3) 9_656 ?
In1 O1 2.157(3) 12_655 ?
In1 O1 2.157(3) 9_656 ?
In1 O1 2.157(3) . ?
In1 O1 2.157(3) 4_556 ?
N1 O3 1.26(3) . ?
N1 O4 1.289(18) . ?
N1 C1 1.35(3) . ?
O1 C3 1.244(4) . ?
O2 In1 2.080(3) 2_655 ?
O3 O3 1.50(5) 11 ?
O4 O4 1.31(5) 11 ?
C1 C2 1.373(8) . ?
C1 C1 1.389(13) 7_546 ?
C2 C1 1.373(8) 11_565 ?
C2 C3 1.510(10) . ?
C3 O1 1.245(4) 11_565 ?

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
O2 In1 O2 180.0 . 9_656 ?
O2 In1 O1 89.96(13) . 12_655 ?
O2 In1 O1 90.04(13) 9_656 12_655 ?
O2 In1 O1 90.04(13) . 9_656 ?
O2 In1 O1 89.96(13) 9_656 9_656 ?
O1 In1 O1 86.7(2) 12_655 9_656 ?
O2 In1 O1 89.96(13) . . ?
O2 In1 O1 90.04(13) 9_656 . ?
O1 In1 O1 93.3(2) 12_655 . ?
O1 In1 O1 180.00(15) 9_656 . ?
O2 In1 O1 90.04(13) . 4_556 ?
O2 In1 O1 89.96(13) 9_656 4_556 ?
O1 In1 O1 180.00(12) 12_655 4_556 ?
O1 In1 O1 93.3(2) 9_656 4_556 ?
O1 In1 O1 86.7(2) . 4_556 ?
O3 N1 O4 125(3) . . ?
O3 N1 C1 120(2) . . ?
O4 N1 C1 115(2) . . ?
C3 O1 In1 134.6(4) . . ?
In1 O2 In1 122.7(3) . 2_655 ?
N1 O3 O3 113.0(18) . 11 ?
N1 O4 O4 117.0(18) . 11 ?
N1 C1 C2 125.4(12) . . ?
N1 C1 C1 113.8(11) . 7_546 ?
C2 C1 C1 120.8(4) . 7_546 ?
C1 C2 C1 118.3(8) . 11_565 ?
C1 C2 C3 120.8(4) . . ?
C1 C2 C3 120.8(4) 11_565 . ?
O1 C3 O1 127.1(6) . 11_565 ?
O1 C3 C2 116.4(3) . . ?
O1 C3 C2 116.4(3) 11_565 . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.474
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.194
