# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2203979'
loop_
_audit_author_name
_audit_author_address
'Dechambenoit Pierre'
;University of Bordeaux
France
;
_audit_update_record             
;
2022-08-29 deposited with the CCDC.	2022-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 Br4 In N O, C12 H8 N O'
_chemical_formula_sum            'C24 H17 Br4 In N2 O2'
_chemical_formula_weight         799.85

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   34.562(4)
_cell_length_b                   7.6912(10)
_cell_length_c                   19.859(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.002(14)
_cell_angle_gamma                90
_cell_volume                     5020.5(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2238
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      19.53

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.116
_exptl_crystal_F_000             3040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    7.333
_shelx_estimated_absorpt_T_min   0.406
_shelx_estimated_absorpt_T_max   0.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5994
_exptl_absorpt_correction_T_max  0.7444
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II Quasar'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36527
_diffrn_reflns_av_unetI/netI     0.0778
_diffrn_reflns_av_R_equivalents  0.1802
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.479
_diffrn_reflns_theta_max         19.933
_diffrn_reflns_theta_full        19.933
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.966
_reflns_number_total             2247
_reflns_number_gt                1691
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Intrinsic Phasing (Bruker)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
The data were cut at 1.05 angstrom as there is no diffraction 
above and Rint becomes larger. The result is a low thetamax value 
as well as poor resolution and data/parameters ratio.
The crystal is a very thin needle. Its very small size makes 
the diffraction very low. In addition, the anisotropic shape makes 
the diffraction strongly dependent of the orientation of the crystal 
so that several reflections at "high" angles were not present.
All non-hydrogens were refined anisotropically. Hydrogen atoms were assigned to 
ideal positions and refined isotropically using a riding model.
Due to some the very low resolution (together with some probable slight disorder), 
some of the thermal ellipsoids were found to be meaningless (nearly 2D), so that 
SIMU restraints were applied.
;
_vrf_THETM01_shelx               
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
            Calculated sin(theta_max)/wavelength =    0.4797
RESPONSE: The data were cut at 1.05 angstrom as there is no diffraction 
above and Rint becomes larger. The result is a low thetamax value 
as well as poor resolution and data/parameters ratio.
;
_vrf_PLAT342_shelx               
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.03 Ang.
RESPONSE: The data were cut at 1.05 angstrom as there is no diffraction 
above and Rint becomes larger. The result is a low thetamax value 
as well as poor resolution and data/parameters ratio.
;
_vrf_PLAT088_shelx               
;
PROBLEM: Poor Data / Parameter Ratio ....................       7.54 Note
RESPONSE: The data were cut at 1.05 angstrom as there is no diffraction 
above and Rint becomes larger. The result is a low thetamax value 
as well as poor resolution and data/parameters ratio. 
;
_vrf_RINTA01_shelx               
;
PROBLEM: The value of Rint is greater than 0.18
            Rint given   0.180
RESPONSE: The crystal is a very thin needle. Its very small size makes 
the diffraction very low, at low resolution. In addition, the anisotropic shape makes 
the diffraction strongly dependent of the orientation of the crystal 
so that several reflections at "high" angles were not present. One could cut the data 
at even lower angles to decrease this Rint, but this would result in a lower bond precisions.
We believe this cutoff at 1.05 angstrom being the best compromise.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0001P)²+272.5915P] 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         2247
_refine_ls_number_parameters     298
_refine_ls_number_restraints     108
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0602
_refine_ls_wR_factor_ref         0.1175
_refine_ls_wR_factor_gt          0.1057
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_restrained_S_all      1.114
_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 0.88736(4) 0.68068(15) 0.55320(8) 0.0225(4) Uani 1 1 d . . . . .
Br4 Br 0.92429(5) 0.3877(2) 0.56640(11) 0.0306(6) Uani 1 1 d . . . . .
Br1 Br 0.82718(6) 0.5628(2) 0.44492(12) 0.0337(6) Uani 1 1 d . . . . .
Br2 Br 0.93693(6) 0.8049(2) 0.67150(12) 0.0350(6) Uani 1 1 d . . . . .
Br3 Br 0.91713(6) 0.8712(2) 0.47351(12) 0.0363(6) Uani 1 1 d . . . . .
O1 O 0.8487(3) 0.5724(13) 0.6222(7) 0.024(3) Uani 1 1 d . . . . .
N1 N 0.8405(4) 0.8850(17) 0.5641(8) 0.024(4) Uani 1 1 d . U . . .
C5 C 0.8120(5) 0.835(2) 0.5947(10) 0.024(5) Uani 1 1 d . U . . .
N2 N 0.5505(5) 0.394(2) 0.6433(9) 0.038(4) Uani 1 1 d . U . . .
C3 C 0.7832(5) 1.116(2) 0.5819(10) 0.026(5) Uani 1 1 d . . . . .
H3 H 0.763729 1.196942 0.588075 0.031 Uiso 1 1 calc R U . . .
C6 C 0.8170(6) 0.652(2) 0.6214(10) 0.026(5) Uani 1 1 d . . . . .
C4 C 0.7825(5) 0.945(2) 0.6035(10) 0.027(5) Uani 1 1 d . . . . .
H4 H 0.762478 0.905779 0.623715 0.032 Uiso 1 1 calc R U . . .
C12 C 0.8011(6) 0.466(2) 0.7097(11) 0.028(5) Uani 1 1 d . U . . .
H12 H 0.829608 0.457077 0.731872 0.034 Uiso 1 1 calc R U . . .
C8 C 0.7446(5) 0.5712(19) 0.6143(10) 0.021(4) Uani 1 1 d . U . . .
H8 H 0.734161 0.636043 0.571819 0.026 Uiso 1 1 calc R U . . .
O2 O 0.6519(4) 0.420(3) 0.7474(9) 0.088(7) Uani 1 1 d . . . . .
C19 C 0.5513(5) 0.558(2) 0.6751(11) 0.027(5) Uani 1 1 d . U . . .
C1 C 0.8410(5) 1.049(2) 0.5432(10) 0.029(5) Uani 1 1 d . U . . .
H1 H 0.861100 1.085600 0.522631 0.035 Uiso 1 1 calc R U . . .
C7 C 0.7868(5) 0.5696(19) 0.6498(11) 0.023(4) Uani 1 1 d . U . . .
C9 C 0.7190(5) 0.480(2) 0.6406(12) 0.029(5) Uani 1 1 d . U . . .
H9 H 0.690625 0.483207 0.616039 0.035 Uiso 1 1 calc R U . . .
C2 C 0.8121(5) 1.170(2) 0.5513(11) 0.032(6) Uani 1 1 d . . . . .
H2 H 0.812437 1.286887 0.535975 0.038 Uiso 1 1 calc R U . . .
C11 C 0.7754(6) 0.376(2) 0.7382(11) 0.034(6) Uani 1 1 d . . . . .
H11 H 0.785846 0.310923 0.780639 0.041 Uiso 1 1 calc R U . . .
C14 C 0.5900(6) 0.323(2) 0.6666(12) 0.040(5) Uani 1 1 d . U . . .
C24 C 0.5898(6) 0.594(2) 0.7213(12) 0.040(5) Uani 1 1 d . U . . .
C10 C 0.7328(6) 0.384(3) 0.7023(13) 0.043(6) Uani 1 1 d . . . . .
H10 H 0.714108 0.323166 0.720302 0.051 Uiso 1 1 calc R U . . .
C13 C 0.6170(7) 0.441(3) 0.7177(13) 0.046(6) Uani 1 1 d . U . . .
C20 C 0.5199(7) 0.681(3) 0.6657(12) 0.050(5) Uani 1 1 d . U . . .
H20 H 0.493163 0.658641 0.635131 0.061 Uiso 1 1 calc R U . . .
C23 C 0.5983(7) 0.749(3) 0.7589(13) 0.056(6) Uani 1 1 d . U . . .
H23 H 0.624379 0.772977 0.791310 0.068 Uiso 1 1 calc R U . . .
C16 C 0.5597(9) 0.079(3) 0.5928(14) 0.069(6) Uani 1 1 d . U . . .
H16 H 0.562377 -0.031171 0.572664 0.083 Uiso 1 1 calc R U . . .
C17 C 0.5237(8) 0.156(3) 0.5745(14) 0.069(6) Uani 1 1 d . U . . .
H17 H 0.500961 0.096878 0.543554 0.083 Uiso 1 1 calc R U . . .
C15 C 0.5945(8) 0.155(3) 0.6418(14) 0.063(6) Uani 1 1 d . U . . .
H15 H 0.619763 0.096004 0.657241 0.076 Uiso 1 1 calc R U . . .
C18 C 0.5181(7) 0.319(3) 0.5987(12) 0.053(5) Uani 1 1 d . U . . .
H18 H 0.492308 0.375082 0.584142 0.063 Uiso 1 1 calc R U . . .
C22 C 0.5680(9) 0.863(3) 0.7471(14) 0.069(6) Uani 1 1 d . U . . .
H22 H 0.573667 0.971390 0.771254 0.083 Uiso 1 1 calc R U . . .
C21 C 0.5300(8) 0.837(3) 0.7039(13) 0.062(6) Uani 1 1 d . U . . .
H21 H 0.509971 0.925045 0.699011 0.074 Uiso 1 1 calc R U . . .


_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 N1 2.313(13) . ?
In1 O1 2.344(11) . ?
In1 Br4 2.563(2) . ?
In1 Br3 2.592(2) . ?
In1 Br2 2.623(3) . ?
In1 Br1 2.647(2) . ?
O1 C6 1.251(19) . ?
N1 C1 1.33(2) . ?
N1 C5 1.37(2) . ?
C5 C4 1.38(2) . ?
C5 C6 1.49(2) . ?
N2 C18 1.33(2) . ?
N2 C14 1.41(2) . ?
N2 C19 1.41(2) . ?
C3 C2 1.38(2) . ?
C3 C4 1.39(2) . ?
C3 H3 0.9500 . ?
C6 C7 1.47(2) . ?
C4 H4 0.9500 . ?
C12 C11 1.38(2) . ?
C12 C7 1.39(2) . ?
C12 H12 0.9500 . ?
C8 C9 1.35(2) . ?
C8 C7 1.41(2) . ?
C8 H8 0.9500 . ?
O2 C13 1.18(2) . ?
C19 C24 1.39(3) . ?
C19 C20 1.40(3) . ?
C1 C2 1.41(2) . ?
C1 H1 0.9500 . ?
C9 C10 1.39(3) . ?
C9 H9 0.9500 . ?
C2 H2 0.9500 . ?
C11 C10 1.43(2) . ?
C11 H11 0.9500 . ?
C14 C15 1.41(3) . ?
C14 C13 1.46(3) . ?
C24 C23 1.39(3) . ?
C24 C13 1.52(3) . ?
C10 H10 0.9500 . ?
C20 C21 1.41(3) . ?
C20 H20 0.9500 . ?
C23 C22 1.33(3) . ?
C23 H23 0.9500 . ?
C16 C17 1.33(3) . ?
C16 C15 1.42(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.38(3) . ?
C17 H17 0.9500 . ?
C15 H15 0.9500 . ?
C18 H18 0.9500 . ?
C22 C21 1.34(3) . ?
C22 H22 0.9500 . ?
C21 H21 0.9500 . ?

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
N1 In1 O1 69.2(5) . . ?
N1 In1 Br4 158.2(4) . . ?
O1 In1 Br4 89.1(3) . . ?
N1 In1 Br3 95.4(4) . . ?
O1 In1 Br3 164.6(3) . . ?
Br4 In1 Br3 106.30(8) . . ?
N1 In1 Br2 87.2(3) . . ?
O1 In1 Br2 86.5(3) . . ?
Br4 In1 Br2 93.56(7) . . ?
Br3 In1 Br2 93.91(8) . . ?
N1 In1 Br1 84.9(3) . . ?
O1 In1 Br1 84.6(3) . . ?
Br4 In1 Br1 91.33(7) . . ?
Br3 In1 Br1 93.33(8) . . ?
Br2 In1 Br1 169.77(9) . . ?
C6 O1 In1 118.3(11) . . ?
C1 N1 C5 119.2(15) . . ?
C1 N1 In1 122.7(12) . . ?
C5 N1 In1 118.1(10) . . ?
N1 C5 C4 123.0(16) . . ?
N1 C5 C6 113.9(15) . . ?
C4 C5 C6 123.0(18) . . ?
C18 N2 C14 125.8(18) . . ?
C18 N2 C19 125.7(18) . . ?
C14 N2 C19 108.5(16) . . ?
C2 C3 C4 120.3(16) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
O1 C6 C7 120.4(15) . . ?
O1 C6 C5 118.0(16) . . ?
C7 C6 C5 121.5(16) . . ?
C5 C4 C3 117.5(18) . . ?
C5 C4 H4 121.2 . . ?
C3 C4 H4 121.2 . . ?
C11 C12 C7 122.5(17) . . ?
C11 C12 H12 118.8 . . ?
C7 C12 H12 118.8 . . ?
C9 C8 C7 120.1(18) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C24 C19 C20 120.0(19) . . ?
C24 C19 N2 110.7(16) . . ?
C20 C19 N2 129.3(18) . . ?
N1 C1 C2 120.8(18) . . ?
N1 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C12 C7 C8 118.2(16) . . ?
C12 C7 C6 117.9(16) . . ?
C8 C7 C6 123.4(17) . . ?
C8 C9 C10 122.1(18) . . ?
C8 C9 H9 119.0 . . ?
C10 C9 H9 119.0 . . ?
C3 C2 C1 119.2(17) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C12 C11 C10 118.1(18) . . ?
C12 C11 H11 121.0 . . ?
C10 C11 H11 121.0 . . ?
C15 C14 N2 116(2) . . ?
C15 C14 C13 134(2) . . ?
N2 C14 C13 109.5(16) . . ?
C19 C24 C23 122(2) . . ?
C19 C24 C13 107.3(18) . . ?
C23 C24 C13 131(2) . . ?
C9 C10 C11 118.9(17) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
O2 C13 C14 127(2) . . ?
O2 C13 C24 130(2) . . ?
C14 C13 C24 104.0(18) . . ?
C19 C20 C21 117(2) . . ?
C19 C20 H20 121.7 . . ?
C21 C20 H20 121.7 . . ?
C22 C23 C24 117(2) . . ?
C22 C23 H23 121.7 . . ?
C24 C23 H23 121.7 . . ?
C17 C16 C15 122(2) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C16 C17 C18 122(2) . . ?
C16 C17 H17 118.8 . . ?
C18 C17 H17 118.8 . . ?
C14 C15 C16 117(2) . . ?
C14 C15 H15 121.3 . . ?
C16 C15 H15 121.3 . . ?
N2 C18 C17 117(2) . . ?
N2 C18 H18 121.7 . . ?
C17 C18 H18 121.7 . . ?
C23 C22 C21 125(2) . . ?
C23 C22 H22 117.4 . . ?
C21 C22 H22 117.4 . . ?
C22 C21 C20 120(2) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?

_refine_diff_density_max         0.727
_refine_diff_density_min         -0.913
_refine_diff_density_rms         0.167

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2203980'
loop_
_audit_author_name
_audit_author_address
'Dechambenoit Pierre'
;University of Bordeaux
France
;
_audit_update_record             
;
2022-08-29 deposited with the CCDC.	2022-09-28 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         'C14 H15 Cl3 In N O2, C12 H9 N O'
_chemical_formula_sum            'C26 H24 Cl3 In N2 O3'
_chemical_formula_weight         633.64

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   17.5180(9)
_cell_length_b                   7.7740(4)
_cell_length_c                   19.4933(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.390(2)
_cell_angle_gamma                90
_cell_volume                     2611.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9860
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      26.05

_exptl_crystal_description       parallelipiped
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_F_000             1272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.243
_shelx_estimated_absorpt_T_min   0.599
_shelx_estimated_absorpt_T_max   0.940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6321
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II Quasar'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            86266
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_av_R_equivalents  0.0725
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.124
_diffrn_reflns_theta_max         28.906
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6788
_reflns_number_gt                5634
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Intrinsic Phasing (Bruker)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
All non-hydrogens were refined anisotropically. Hydrogen atoms were 
assigned to ideal positions and refined isotropically using a riding 
model, except H2ET which was introduced based on the residual electronic
density found in the difference Fourier map, and refined using a DFIX constraint.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0213P)²+1.0526P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6788
_refine_ls_number_parameters     320
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0250
_refine_ls_wR_factor_ref         0.0554
_refine_ls_wR_factor_gt          0.0516
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.002
_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 0.23351(2) 0.35690(2) 0.47137(2) 0.01292(4) Uani 1 1 d . . . . .
Cl2 Cl 0.26181(3) 0.52853(6) 0.37638(2) 0.02182(11) Uani 1 1 d . . . . .
Cl3 Cl 0.30517(3) 0.09546(6) 0.46951(2) 0.02218(11) Uani 1 1 d . . . . .
Cl1 Cl 0.10738(3) 0.25209(6) 0.41200(2) 0.02261(11) Uani 1 1 d . . . . .
O2 O 0.33042(8) 0.47959(17) 0.54243(6) 0.0193(3) Uani 1 1 d D . . . .
O1 O 0.18957(7) 0.26721(16) 0.57332(6) 0.0161(3) Uani 1 1 d . . . . .
O3 O 0.31023(8) 0.08414(17) 0.70428(7) 0.0221(3) Uani 1 1 d . . . . .
N1 N 0.17032(9) 0.57648(19) 0.51700(7) 0.0143(3) Uani 1 1 d . . . . .
N2 N 0.31410(9) 0.5174(2) 0.67539(7) 0.0166(3) Uani 1 1 d . . . . .
C6 C 0.13569(11) 0.3521(2) 0.58897(9) 0.0143(4) Uani 1 1 d . . . . .
C5 C 0.12604(11) 0.5341(2) 0.56461(9) 0.0142(4) Uani 1 1 d . . . . .
C16 C 0.27259(12) 0.3939(3) 0.77510(9) 0.0210(4) Uani 1 1 d . . . . .
H16 H 0.2705 0.2971 0.8045 0.025 Uiso 1 1 calc R U . . .
C25 C 0.40769(11) 0.5045(2) 0.52849(10) 0.0185(4) Uani 1 1 d . . . . .
H25A H 0.4071 0.4954 0.4777 0.022 Uiso 1 1 calc R U . . .
H25B H 0.4425 0.4140 0.5523 0.022 Uiso 1 1 calc R U . . .
C7 C 0.08453(11) 0.2752(2) 0.63331(9) 0.0143(4) Uani 1 1 d . . . . .
C4 C 0.08234(11) 0.6558(2) 0.59205(9) 0.0173(4) Uani 1 1 d . . . . .
H4 H 0.0519 0.6241 0.6257 0.021 Uiso 1 1 calc R U . . .
C8 C 0.00492(11) 0.3049(2) 0.62088(9) 0.0172(4) Uani 1 1 d . . . . .
H8 H -0.0176 0.3828 0.5854 0.021 Uiso 1 1 calc R U . . .
C9 C -0.04145(12) 0.2199(3) 0.66081(10) 0.0217(4) Uani 1 1 d . . . . .
H9 H -0.0961 0.2367 0.6515 0.026 Uiso 1 1 calc R U . . .
C3 C 0.08376(12) 0.8251(2) 0.56945(10) 0.0203(4) Uani 1 1 d . . . . .
H3 H 0.0527 0.9102 0.5861 0.024 Uiso 1 1 calc R U . . .
C19 C 0.42297(11) 0.2206(2) 0.67927(9) 0.0159(4) Uani 1 1 d . . . . .
C13 C 0.28001(12) 0.6643(2) 0.68814(10) 0.0194(4) Uani 1 1 d . . . . .
H13 H 0.2823 0.7590 0.6577 0.023 Uiso 1 1 calc R U . . .
C17 C 0.31011(11) 0.3842(2) 0.71857(9) 0.0165(4) Uani 1 1 d . . . . .
C23 C 0.51294(12) 0.0875(3) 0.61587(10) 0.0220(4) Uani 1 1 d . . . . .
H23 H 0.5246 0.0009 0.5849 0.026 Uiso 1 1 calc R U . . .
C26 C 0.43731(13) 0.6787(3) 0.55412(12) 0.0284(5) Uani 1 1 d . . . . .
H26A H 0.4017 0.7676 0.5317 0.043 Uiso 1 1 calc R U . . .
H26B H 0.4889 0.6972 0.5426 0.043 Uiso 1 1 calc R U . . .
H26C H 0.4407 0.6849 0.6048 0.043 Uiso 1 1 calc R U . . .
C24 C 0.44076(11) 0.0912(2) 0.63525(9) 0.0181(4) Uani 1 1 d . . . . .
H24 H 0.4033 0.0055 0.6185 0.022 Uiso 1 1 calc R U . . .
C15 C 0.23818(12) 0.5481(3) 0.78777(10) 0.0248(5) Uani 1 1 d . . . . .
H15 H 0.2125 0.5592 0.8265 0.030 Uiso 1 1 calc R U . . .
C1 C 0.17350(11) 0.7399(2) 0.49763(9) 0.0180(4) Uani 1 1 d . . . . .
H1 H 0.2062 0.7699 0.4655 0.022 Uiso 1 1 calc R U . . .
C18 C 0.34553(11) 0.2177(2) 0.70053(9) 0.0164(4) Uani 1 1 d . . . . .
C12 C 0.11761(12) 0.1630(2) 0.68640(9) 0.0183(4) Uani 1 1 d . . . . .
H12 H 0.1718 0.1406 0.6943 0.022 Uiso 1 1 calc R U . . .
C2 C 0.13078(12) 0.8679(2) 0.52270(10) 0.0209(4) Uani 1 1 d . . . . .
H2 H 0.1340 0.9836 0.5078 0.025 Uiso 1 1 calc R U . . .
C14 C 0.24148(12) 0.6854(3) 0.74363(10) 0.0235(4) Uani 1 1 d . . . . .
H14 H 0.2178 0.7921 0.7511 0.028 Uiso 1 1 calc R U . . .
C10 C -0.00836(12) 0.1109(3) 0.71399(10) 0.0230(4) Uani 1 1 d . . . . .
H10 H -0.0403 0.0539 0.7414 0.028 Uiso 1 1 calc R U . . .
C20 C 0.47833(12) 0.3441(3) 0.70434(10) 0.0221(4) Uani 1 1 d . . . . .
H20 H 0.4662 0.4333 0.7339 0.027 Uiso 1 1 calc R U . . .
C11 C 0.07086(12) 0.0845(3) 0.72751(10) 0.0216(4) Uani 1 1 d . . . . .
H11 H 0.0934 0.0124 0.7651 0.026 Uiso 1 1 calc R U . . .
C21 C 0.55128(12) 0.3372(3) 0.68618(11) 0.0265(5) Uani 1 1 d . . . . .
H21 H 0.5896 0.4197 0.7044 0.032 Uiso 1 1 calc R U . . .
C22 C 0.56821(12) 0.2096(3) 0.64146(10) 0.0238(4) Uani 1 1 d . . . . .
H22 H 0.6179 0.2062 0.6284 0.029 Uiso 1 1 calc R U . . .
H2ET H 0.3308(13) 0.486(3) 0.5887(5) 0.029 Uiso 1 1 d D U . . .


_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 2.2051(13) . ?
In1 N1 2.2991(15) . ?
In1 O1 2.3623(12) . ?
In1 Cl3 2.3926(5) . ?
In1 Cl2 2.4053(4) . ?
In1 Cl1 2.4419(5) . ?
O2 C25 1.441(2) . ?
O2 H2ET 0.903(9) . ?
O1 C6 1.234(2) . ?
O3 C18 1.217(2) . ?
N1 C1 1.329(2) . ?
N1 C5 1.353(2) . ?
N2 C13 1.333(2) . ?
N2 C17 1.344(2) . ?
C6 C7 1.479(2) . ?
C6 C5 1.492(3) . ?
C5 C4 1.384(3) . ?
C16 C17 1.383(3) . ?
C16 C15 1.384(3) . ?
C16 H16 0.9500 . ?
C25 C26 1.503(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C7 C8 1.391(3) . ?
C7 C12 1.397(3) . ?
C4 C3 1.390(3) . ?
C4 H4 0.9500 . ?
C8 C9 1.389(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.383(3) . ?
C9 H9 0.9500 . ?
C3 C2 1.375(3) . ?
C3 H3 0.9500 . ?
C19 C20 1.389(3) . ?
C19 C24 1.394(3) . ?
C19 C18 1.489(3) . ?
C13 C14 1.384(3) . ?
C13 H13 0.9500 . ?
C17 C18 1.505(3) . ?
C23 C22 1.383(3) . ?
C23 C24 1.384(3) . ?
C23 H23 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C24 H24 0.9500 . ?
C15 C14 1.379(3) . ?
C15 H15 0.9500 . ?
C1 C2 1.386(3) . ?
C1 H1 0.9500 . ?
C12 C11 1.386(3) . ?
C12 H12 0.9500 . ?
C2 H2 0.9500 . ?
C14 H14 0.9500 . ?
C10 C11 1.381(3) . ?
C10 H10 0.9500 . ?
C20 C21 1.387(3) . ?
C20 H20 0.9500 . ?
C11 H11 0.9500 . ?
C21 C22 1.387(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?

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 N1 78.79(5) . . ?
O2 In1 O1 85.98(4) . . ?
N1 In1 O1 68.96(5) . . ?
O2 In1 Cl3 91.74(4) . . ?
N1 In1 Cl3 157.99(4) . . ?
O1 In1 Cl3 90.77(3) . . ?
O2 In1 Cl2 90.09(4) . . ?
N1 In1 Cl2 93.81(4) . . ?
O1 In1 Cl2 162.75(3) . . ?
Cl3 In1 Cl2 106.143(17) . . ?
O2 In1 Cl1 166.01(3) . . ?
N1 In1 Cl1 88.48(4) . . ?
O1 In1 Cl1 84.03(3) . . ?
Cl3 In1 Cl1 98.153(18) . . ?
Cl2 In1 Cl1 96.588(17) . . ?
C25 O2 In1 125.63(10) . . ?
C25 O2 H2ET 110.0(14) . . ?
In1 O2 H2ET 121.3(14) . . ?
C6 O1 In1 115.45(11) . . ?
C1 N1 C5 119.10(16) . . ?
C1 N1 In1 123.49(12) . . ?
C5 N1 In1 117.39(12) . . ?
C13 N2 C17 117.89(16) . . ?
O1 C6 C7 119.93(16) . . ?
O1 C6 C5 118.45(16) . . ?
C7 C6 C5 121.58(16) . . ?
N1 C5 C4 121.59(16) . . ?
N1 C5 C6 113.78(15) . . ?
C4 C5 C6 124.34(16) . . ?
C17 C16 C15 118.29(18) . . ?
C17 C16 H16 120.9 . . ?
C15 C16 H16 120.9 . . ?
O2 C25 C26 109.76(15) . . ?
O2 C25 H25A 109.7 . . ?
C26 C25 H25A 109.7 . . ?
O2 C25 H25B 109.7 . . ?
C26 C25 H25B 109.7 . . ?
H25A C25 H25B 108.2 . . ?
C8 C7 C12 120.12(17) . . ?
C8 C7 C6 121.66(16) . . ?
C12 C7 C6 118.13(17) . . ?
C5 C4 C3 118.85(17) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C9 C8 C7 119.49(18) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C10 C9 C8 120.21(19) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C2 C3 C4 119.07(18) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C20 C19 C24 119.75(18) . . ?
C20 C19 C18 121.73(17) . . ?
C24 C19 C18 118.46(17) . . ?
N2 C13 C14 123.04(18) . . ?
N2 C13 H13 118.5 . . ?
C14 C13 H13 118.5 . . ?
N2 C17 C16 122.89(17) . . ?
N2 C17 C18 116.52(15) . . ?
C16 C17 C18 120.52(17) . . ?
C22 C23 C24 120.11(18) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C23 C24 C19 120.00(18) . . ?
C23 C24 H24 120.0 . . ?
C19 C24 H24 120.0 . . ?
C14 C15 C16 119.38(18) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
N1 C1 C2 122.20(17) . . ?
N1 C1 H1 118.9 . . ?
C2 C1 H1 118.9 . . ?
O3 C18 C19 121.88(17) . . ?
O3 C18 C17 118.99(17) . . ?
C19 C18 C17 119.13(16) . . ?
C11 C12 C7 119.58(19) . . ?
C11 C12 H12 120.2 . . ?
C7 C12 H12 120.2 . . ?
C3 C2 C1 119.11(18) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C15 C14 C13 118.50(18) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C11 C10 C9 120.35(18) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C21 C20 C19 119.99(18) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C10 C11 C12 120.17(18) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C22 C21 C20 119.95(19) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C23 C22 C21 120.16(19) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?

_refine_diff_density_max         0.473
_refine_diff_density_min         -0.716
_refine_diff_density_rms         0.083

####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2203981'
loop_
_audit_author_name
_audit_author_address
'Dechambenoit Pierre'
;University of Bordeaux
France
;
_audit_update_record             
;
2022-08-29 deposited with the CCDC.	2022-09-28 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         'C28 H32 Br4 In2 N2 O4'
_chemical_formula_sum            'C28 H32 Br4 In2 N2 O4'
_chemical_formula_weight         1009.83

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   12.4217(9)
_cell_length_b                   10.4041(7)
_cell_length_c                   25.5262(19)
_cell_angle_alpha                90
_cell_angle_beta                 90.439(4)
_cell_angle_gamma                90
_cell_volume                     3298.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9028
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      27.33

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.033
_exptl_crystal_F_000             1936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    6.278
_shelx_estimated_absorpt_T_min   0.239
_shelx_estimated_absorpt_T_max   0.834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5044
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II Quasar'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            153532
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.596
_diffrn_reflns_theta_max         27.556
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7611
_reflns_number_gt                6358
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Intrinsic Phasing (Bruker)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
All non-hydrogens were refined anisotropically. Hydrogen atoms were 
assigned to ideal positions and refined isotropically using a riding 
model, except those on the oxygen atom of coordinated ethanol, which 
were found on the difference density map and introduced using DFIX 
constraints.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0271P)²+24.9235P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7611
_refine_ls_number_parameters     369
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.0916
_refine_ls_wR_factor_gt          0.0841
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_restrained_S_all      1.127
_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_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
In2 In 0.31885(3) 0.24684(3) 0.63220(2) 0.01532(8) Uani 1 1 d . . . . .
In1 In 0.19244(3) 0.54076(3) 0.61663(2) 0.01459(8) Uani 1 1 d . . . . .
Br4 Br 0.49821(4) 0.35264(5) 0.66563(2) 0.02312(12) Uani 1 1 d . . . . .
Br1 Br 0.11870(4) 0.74311(5) 0.65866(2) 0.02269(12) Uani 1 1 d . . . . .
Br2 Br 0.00942(4) 0.43703(5) 0.58828(2) 0.02343(12) Uani 1 1 d . . . . .
Br3 Br 0.41129(5) 0.05735(5) 0.58953(2) 0.02697(13) Uani 1 1 d . . . . .
O2 O 0.2224(3) 0.3898(3) 0.67144(12) 0.0144(7) Uani 1 1 d . . . . .
O1 O 0.2853(3) 0.3937(3) 0.57599(12) 0.0151(7) Uani 1 1 d . . . . .
O4 O 0.1530(3) 0.1756(4) 0.60519(15) 0.0235(8) Uani 1 1 d D . . . .
O3 O 0.3567(3) 0.6069(4) 0.64674(16) 0.0264(8) Uani 1 1 d D . . . .
N2 N 0.2683(3) 0.1584(4) 0.70793(16) 0.0173(8) Uani 1 1 d . . . . .
N1 N 0.2455(3) 0.6281(4) 0.54052(16) 0.0183(9) Uani 1 1 d . . . . .
C17 C 0.1996(4) 0.2269(4) 0.73736(18) 0.0141(9) Uani 1 1 d . . . . .
C12 C 0.3618(4) 0.2305(5) 0.4661(2) 0.0223(11) Uani 1 1 d . . . . .
H12 H 0.4335 0.2238 0.4791 0.027 Uiso 1 1 calc R U . . .
C7 C 0.2941(4) 0.3252(5) 0.48548(18) 0.0165(10) Uani 1 1 d . . . . .
C5 C 0.3096(4) 0.5567(5) 0.51028(19) 0.0171(10) Uani 1 1 d . . . . .
C18 C 0.1633(4) 0.3574(5) 0.71630(18) 0.0157(9) Uani 1 1 d . . . . .
H18 H 0.0856 0.3509 0.7061 0.019 Uiso 1 1 calc R U . . .
C19 C 0.1746(4) 0.4621(5) 0.75744(18) 0.0177(10) Uani 1 1 d . . . . .
C6 C 0.3334(4) 0.4189(5) 0.52736(18) 0.0168(10) Uani 1 1 d . . . . .
H6 H 0.4131 0.4089 0.5314 0.020 Uiso 1 1 calc R U . . .
C8 C 0.1899(4) 0.3339(5) 0.4662(2) 0.0230(11) Uani 1 1 d . . . . .
H8 H 0.1431 0.3985 0.4792 0.028 Uiso 1 1 calc R U . . .
C11 C 0.3254(5) 0.1452(5) 0.4278(2) 0.0258(12) Uani 1 1 d . . . . .
H11 H 0.3723 0.0809 0.4147 0.031 Uiso 1 1 calc R U . . .
C13 C 0.2978(4) 0.0396(5) 0.7239(2) 0.0236(11) Uani 1 1 d . . . . .
H13 H 0.3462 -0.0085 0.7030 0.028 Uiso 1 1 calc R U . . .
C14 C 0.2604(5) -0.0141(5) 0.7696(2) 0.0264(12) Uani 1 1 d . . . . .
H14 H 0.2817 -0.0982 0.7798 0.032 Uiso 1 1 calc R U . . .
C15 C 0.1912(4) 0.0569(5) 0.8000(2) 0.0244(11) Uani 1 1 d . . . . .
H15 H 0.1651 0.0227 0.8320 0.029 Uiso 1 1 calc R U . . .
C10 C 0.2216(5) 0.1540(5) 0.4090(2) 0.0273(12) Uani 1 1 d . . . . .
H10 H 0.1966 0.0955 0.3830 0.033 Uiso 1 1 calc R U . . .
C4 C 0.3544(4) 0.6070(5) 0.4647(2) 0.0205(10) Uani 1 1 d . . . . .
H4 H 0.3984 0.5548 0.4431 0.025 Uiso 1 1 calc R U . . .
C16 C 0.1599(4) 0.1784(5) 0.7837(2) 0.0210(10) Uani 1 1 d . . . . .
H16 H 0.1117 0.2278 0.8043 0.025 Uiso 1 1 calc R U . . .
C2 C 0.2682(5) 0.8072(5) 0.4830(2) 0.0297(13) Uani 1 1 d . . . . .
H2 H 0.2537 0.8946 0.4747 0.036 Uiso 1 1 calc R U . . .
C9 C 0.1530(4) 0.2497(5) 0.4281(2) 0.0259(12) Uani 1 1 d . . . . .
H9 H 0.0814 0.2567 0.4151 0.031 Uiso 1 1 calc R U . . .
C24 C 0.0841(5) 0.5237(6) 0.7768(2) 0.0276(12) Uani 1 1 d . . . . .
H24 H 0.0144 0.4966 0.7659 0.033 Uiso 1 1 calc R U . . .
C21 C 0.2855(6) 0.6011(6) 0.8095(2) 0.0362(15) Uani 1 1 d . . . . .
H21 H 0.3549 0.6270 0.8213 0.043 Uiso 1 1 calc R U . . .
C1 C 0.2237(5) 0.7507(5) 0.5268(2) 0.0281(12) Uani 1 1 d . . . . .
H1 H 0.1764 0.7997 0.5480 0.034 Uiso 1 1 calc R U . . .
C20 C 0.2758(4) 0.5010(5) 0.7740(2) 0.0241(11) Uani 1 1 d . . . . .
H20 H 0.3383 0.4594 0.7610 0.029 Uiso 1 1 calc R U . . .
C3 C 0.3343(5) 0.7333(5) 0.4514(2) 0.0260(12) Uani 1 1 d . . . . .
H3 H 0.3655 0.7694 0.4209 0.031 Uiso 1 1 calc R U . . .
C23 C 0.0950(6) 0.6245(6) 0.8120(2) 0.0400(17) Uani 1 1 d . . . . .
H23 H 0.0326 0.6663 0.8250 0.048 Uiso 1 1 calc R U . . .
C28 C 0.1315(6) 0.0748(6) 0.5683(3) 0.0377(15) Uani 1 1 d . . . . .
H28A H 0.1797 0.0013 0.5760 0.045 Uiso 1 1 calc R U . . .
H28B H 0.1480 0.1060 0.5326 0.045 Uiso 1 1 calc R U . . .
C22 C 0.1949(7) 0.6640(6) 0.8282(2) 0.0425(18) Uani 1 1 d . . . . .
H22 H 0.2023 0.7339 0.8519 0.051 Uiso 1 1 calc R U . . .
C27 C 0.0200(6) 0.0307(7) 0.5696(3) 0.0465(17) Uani 1 1 d . . . . .
H27A H 0.0019 0.0040 0.6052 0.070 Uiso 1 1 calc R U . . .
H27B H 0.0110 -0.0423 0.5457 0.070 Uiso 1 1 calc R U . . .
H27C H -0.0278 0.1008 0.5586 0.070 Uiso 1 1 calc R U . . .
C25 C 0.4945(6) 0.7455(8) 0.6828(3) 0.053(2) Uani 1 1 d . . . . .
H25A H 0.4590 0.7479 0.7169 0.079 Uiso 1 1 calc R U . . .
H25B H 0.5303 0.8278 0.6764 0.079 Uiso 1 1 calc R U . . .
H25C H 0.5480 0.6762 0.6826 0.079 Uiso 1 1 calc R U . . .
C26 C 0.4131(6) 0.7219(7) 0.6411(4) 0.055(2) Uani 1 1 d . . . . .
H26A H 0.3610 0.7939 0.6408 0.066 Uiso 1 1 calc R U . . .
H26B H 0.4497 0.7214 0.6067 0.066 Uiso 1 1 calc R U . . .
H3E H 0.403(5) 0.546(6) 0.658(3) 0.066 Uiso 1 1 d D U . . .
H4E H 0.114(6) 0.248(4) 0.601(3) 0.066 Uiso 1 1 d D U . . .


_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
In2 O1 2.135(3) . ?
In2 O2 2.161(3) . ?
In2 N2 2.235(4) . ?
In2 O4 2.291(4) . ?
In2 Br3 2.5319(6) . ?
In2 Br4 2.6220(6) . ?
In1 O2 2.134(3) . ?
In1 O1 2.184(3) . ?
In1 N1 2.248(4) . ?
In1 O3 2.281(4) . ?
In1 Br1 2.5372(6) . ?
In1 Br2 2.6138(6) . ?
O2 C18 1.406(5) . ?
O1 C6 1.406(6) . ?
O4 C28 1.433(7) . ?
O4 H4E 0.898(10) . ?
O3 C26 1.395(7) . ?
O3 H3E 0.899(10) . ?
N2 C17 1.346(6) . ?
N2 C13 1.351(6) . ?
N1 C5 1.338(6) . ?
N1 C1 1.349(7) . ?
C17 C16 1.381(7) . ?
C17 C18 1.527(6) . ?
C12 C7 1.388(7) . ?
C12 C11 1.393(8) . ?
C12 H12 0.9500 . ?
C7 C8 1.385(7) . ?
C7 C6 1.524(7) . ?
C5 C4 1.395(7) . ?
C5 C6 1.526(7) . ?
C18 C19 1.519(7) . ?
C18 H18 1.0000 . ?
C19 C20 1.383(7) . ?
C19 C24 1.389(7) . ?
C6 H6 1.0000 . ?
C8 C9 1.383(7) . ?
C8 H8 0.9500 . ?
C11 C10 1.376(8) . ?
C11 H11 0.9500 . ?
C13 C14 1.376(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.377(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(7) . ?
C15 H15 0.9500 . ?
C10 C9 1.401(8) . ?
C10 H10 0.9500 . ?
C4 C3 1.380(7) . ?
C4 H4 0.9500 . ?
C16 H16 0.9500 . ?
C2 C1 1.383(8) . ?
C2 C3 1.388(8) . ?
C2 H2 0.9500 . ?
C9 H9 0.9500 . ?
C24 C23 1.387(9) . ?
C24 H24 0.9500 . ?
C21 C20 1.386(8) . ?
C21 C22 1.389(10) . ?
C21 H21 0.9500 . ?
C1 H1 0.9500 . ?
C20 H20 0.9500 . ?
C3 H3 0.9500 . ?
C23 C22 1.369(11) . ?
C23 H23 0.9500 . ?
C28 C27 1.459(9) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C22 H22 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C25 C26 1.483(10) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?

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
O1 In2 O2 73.33(12) . . ?
O1 In2 N2 145.22(14) . . ?
O2 In2 N2 73.86(13) . . ?
O1 In2 O4 81.90(13) . . ?
O2 In2 O4 82.05(13) . . ?
N2 In2 O4 82.49(14) . . ?
O1 In2 Br3 110.78(9) . . ?
O2 In2 Br3 171.99(9) . . ?
N2 In2 Br3 100.53(11) . . ?
O4 In2 Br3 91.63(9) . . ?
O1 In2 Br4 94.54(9) . . ?
O2 In2 Br4 91.89(9) . . ?
N2 In2 Br4 97.75(11) . . ?
O4 In2 Br4 173.63(9) . . ?
Br3 In2 Br4 94.58(2) . . ?
O2 In1 O1 72.87(12) . . ?
O2 In1 N1 144.40(14) . . ?
O1 In1 N1 73.33(13) . . ?
O2 In1 O3 81.37(13) . . ?
O1 In1 O3 84.07(13) . . ?
N1 In1 O3 84.36(15) . . ?
O2 In1 Br1 113.28(9) . . ?
O1 In1 Br1 167.48(9) . . ?
N1 In1 Br1 98.00(11) . . ?
O3 In1 Br1 86.12(10) . . ?
O2 In1 Br2 91.41(9) . . ?
O1 In1 Br2 92.34(9) . . ?
N1 In1 Br2 100.83(11) . . ?
O3 In1 Br2 172.61(10) . . ?
Br1 In1 Br2 98.26(2) . . ?
C18 O2 In1 128.4(3) . . ?
C18 O2 In2 120.5(3) . . ?
In1 O2 In2 107.29(13) . . ?
C6 O1 In2 130.1(3) . . ?
C6 O1 In1 121.2(3) . . ?
In2 O1 In1 106.45(13) . . ?
C28 O4 In2 126.7(4) . . ?
C28 O4 H4E 116(5) . . ?
In2 O4 H4E 104(5) . . ?
C26 O3 In1 132.2(4) . . ?
C26 O3 H3E 108(5) . . ?
In1 O3 H3E 118(5) . . ?
C17 N2 C13 119.2(4) . . ?
C17 N2 In2 116.6(3) . . ?
C13 N2 In2 124.1(3) . . ?
C5 N1 C1 119.6(4) . . ?
C5 N1 In1 117.0(3) . . ?
C1 N1 In1 123.1(4) . . ?
N2 C17 C16 121.1(4) . . ?
N2 C17 C18 117.5(4) . . ?
C16 C17 C18 121.4(4) . . ?
C7 C12 C11 120.5(5) . . ?
C7 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C8 C7 C12 119.1(5) . . ?
C8 C7 C6 120.1(4) . . ?
C12 C7 C6 120.8(5) . . ?
N1 C5 C4 121.0(5) . . ?
N1 C5 C6 118.2(4) . . ?
C4 C5 C6 120.8(4) . . ?
O2 C18 C19 110.2(4) . . ?
O2 C18 C17 110.2(4) . . ?
C19 C18 C17 111.7(4) . . ?
O2 C18 H18 108.2 . . ?
C19 C18 H18 108.2 . . ?
C17 C18 H18 108.2 . . ?
C20 C19 C24 119.5(5) . . ?
C20 C19 C18 120.0(5) . . ?
C24 C19 C18 120.4(5) . . ?
O1 C6 C7 111.3(4) . . ?
O1 C6 C5 110.1(4) . . ?
C7 C6 C5 109.9(4) . . ?
O1 C6 H6 108.5 . . ?
C7 C6 H6 108.5 . . ?
C5 C6 H6 108.5 . . ?
C9 C8 C7 120.8(5) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C10 C11 C12 120.1(5) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
N2 C13 C14 122.3(5) . . ?
N2 C13 H13 118.8 . . ?
C14 C13 H13 118.8 . . ?
C13 C14 C15 118.4(5) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 H14 120.8 . . ?
C14 C15 C16 119.7(5) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C11 C10 C9 119.8(5) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C3 C4 C5 119.4(5) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C17 C16 C15 119.3(5) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C1 C2 C3 118.5(5) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C8 C9 C10 119.7(5) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C23 C24 C19 120.3(6) . . ?
C23 C24 H24 119.8 . . ?
C19 C24 H24 119.8 . . ?
C20 C21 C22 120.8(6) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
N1 C1 C2 122.1(5) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C19 C20 C21 119.6(6) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C4 C3 C2 119.4(5) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C22 C23 C24 120.4(6) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
O4 C28 C27 112.8(6) . . ?
O4 C28 H28A 109.0 . . ?
C27 C28 H28A 109.0 . . ?
O4 C28 H28B 109.0 . . ?
C27 C28 H28B 109.0 . . ?
H28A C28 H28B 107.8 . . ?
C23 C22 C21 119.4(6) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C28 C27 H27A 109.5 . . ?
C28 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C28 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C25 H25A 109.5 . . ?
C26 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C26 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O3 C26 C25 114.1(6) . . ?
O3 C26 H26A 108.7 . . ?
C25 C26 H26A 108.7 . . ?
O3 C26 H26B 108.7 . . ?
C25 C26 H26B 108.7 . . ?
H26A C26 H26B 107.6 . . ?

_refine_diff_density_max         2.439
_refine_diff_density_min         -1.430
_refine_diff_density_rms         0.154

