# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2025

####################################################################### 
# 
# 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_ersh13
_database_code_depnum_ccdc_archive 'CCDC 2361578'
loop_
_audit_author_name
_audit_author_address
'Ilya Yakushev'
;Kurnakov Institute of general and inorganic chemistry, RAS
Russia
;
_audit_update_record             
;
2025-02-15 deposited with the CCDC.	2025-02-18 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         'C28 H30 In2 N4 O2'
_chemical_formula_sum            'C28 H30 In2 N4 O2'
_chemical_formula_weight         684.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0027 0.0018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
In In -0.5973 1.4575 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0071 0.0037 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0124 0.0069 '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                   21.051(6)
_cell_length_b                   10.1465(9)
_cell_length_c                   13.0494(9)
_cell_angle_alpha                90
_cell_angle_beta                 111.090(9)
_cell_angle_gamma                90
_cell_volume                     2600.6(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5953
_cell_measurement_theta_min      2.393
_cell_measurement_theta_max      26.644

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.748
_exptl_crystal_F_000             1360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    2.094
_shelx_estimated_absorpt_T_min   0.834
_shelx_estimated_absorpt_T_max   0.940
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.001
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'XDS (Kabsch, 2010)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.75268
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       φ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2277
_diffrn_reflns_av_unetI/netI     0.0907
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.393
_diffrn_reflns_theta_max         26.644
_diffrn_reflns_theta_full        26.644
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2277
_reflns_number_gt                1994
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Marccd (Doyle, 2011)'
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_reduction        XDS
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;Refined as a 2-component twin.
Due to twinning effects, an unexpected residual electron density is observed
near the oxygen atom O1(1.56 e/A3), about 2.272 A from the indium atom In1.
The second largest residual density (1.44 e/A3) is observed at a distance of
ca. 2.843 A from the heaviest atom.
This electron density does not affect the refinement and is not a consequence
of unaccounted disorder.,Twin
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0774P)²+3.2313P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         2277
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1440
_refine_ls_wR_factor_gt          0.1394
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_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 0.55666(2) 0.85150(3) 0.49261(3) 0.0171(2) Uani 1 1 d . . . . .
O1 O 0.45066(19) 0.9168(4) 0.4473(3) 0.0210(9) Uani 1 1 d . . . . .
N1 N 0.4819(2) 0.6761(5) 0.3949(4) 0.0167(10) Uani 1 1 d . . . . .
N2 N 0.6195(3) 0.6221(5) 0.4725(4) 0.0209(10) Uani 1 1 d . . . . .
C1 C 0.5845(3) 0.7940(6) 0.6620(5) 0.0230(12) Uani 1 1 d . . . . .
H1A H 0.594761 0.699538 0.669321 0.035 Uiso 1 1 calc R U . . .
H1B H 0.546614 0.812581 0.686790 0.035 Uiso 1 1 calc R U . . .
H1C H 0.624727 0.843844 0.707105 0.035 Uiso 1 1 calc R U . . .
C2 C 0.5963(3) 0.9297(6) 0.3742(5) 0.0261(13) Uani 1 1 d . . . . .
H2A H 0.606874 1.023419 0.389195 0.039 Uiso 1 1 calc R U . . .
H2B H 0.562207 0.919445 0.300147 0.039 Uiso 1 1 calc R U . . .
H2C H 0.637769 0.881896 0.379404 0.039 Uiso 1 1 calc R U . . .
C3 C 0.4007(3) 0.8404(5) 0.3905(5) 0.0179(12) Uani 1 1 d . . . . .
C4 C 0.3319(3) 0.8819(6) 0.3564(5) 0.0198(11) Uani 1 1 d . . . . .
H4 H 0.321757 0.966508 0.377552 0.024 Uiso 1 1 calc R U . . .
C5 C 0.2792(3) 0.8016(6) 0.2928(5) 0.0223(12) Uani 1 1 d . . . . .
H5 H 0.233459 0.831417 0.271900 0.027 Uiso 1 1 calc R U . . .
C6 C 0.2925(3) 0.6782(6) 0.2592(5) 0.0235(12) Uani 1 1 d . . . . .
H6 H 0.256160 0.624793 0.213981 0.028 Uiso 1 1 calc R U . . .
C7 C 0.3589(3) 0.6332(6) 0.2920(5) 0.0220(13) Uani 1 1 d . . . . .
H7 H 0.367842 0.548131 0.269892 0.026 Uiso 1 1 calc R U . . .
C8 C 0.4133(3) 0.7117(5) 0.3574(5) 0.0187(11) Uani 1 1 d . . . . .
C9 C 0.5024(3) 0.5601(6) 0.3836(5) 0.0209(11) Uani 1 1 d . . . . .
H9 H 0.469717 0.494054 0.349071 0.025 Uiso 1 1 calc R U . . .
C10 C 0.5753(3) 0.5263(5) 0.4227(5) 0.0196(11) Uani 1 1 d . . . . .
C11 C 0.5959(3) 0.3997(6) 0.4075(5) 0.0216(12) Uani 1 1 d . . . . .
H11 H 0.563157 0.333930 0.372401 0.026 Uiso 1 1 calc R U . . .
C12 C 0.6648(3) 0.3714(6) 0.4444(6) 0.0257(13) Uani 1 1 d . . . . .
H12 H 0.680293 0.286340 0.433923 0.031 Uiso 1 1 calc R U . . .
C13 C 0.7106(3) 0.4696(6) 0.4969(5) 0.0250(12) Uani 1 1 d . . . . .
H13 H 0.758254 0.453332 0.523979 0.030 Uiso 1 1 calc R U . . .
C14 C 0.6849(3) 0.5932(6) 0.5088(5) 0.0257(13) Uani 1 1 d . . . . .
H14 H 0.716428 0.660322 0.545183 0.031 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 C1 2.154(6) . ?
In1 C2 2.154(6) . ?
In1 O1 2.195(4) . ?
In1 N1 2.414(5) . ?
In1 O1 2.500(4) 5_676 ?
In1 N2 2.736(5) . ?
O1 C3 1.303(7) . ?
N1 C9 1.280(7) . ?
N1 C8 1.395(7) . ?
N2 C14 1.318(8) . ?
N2 C10 1.342(7) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.416(8) . ?
C3 C8 1.430(8) . ?
C4 C5 1.386(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.385(9) . ?
C6 H6 0.9500 . ?
C7 C8 1.403(8) . ?
C7 H7 0.9500 . ?
C9 C10 1.472(8) . ?
C9 H9 0.9500 . ?
C10 C11 1.392(8) . ?
C11 C12 1.385(9) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(9) . ?
C12 H12 0.9500 . ?
C13 C14 1.397(9) . ?
C13 H13 0.9500 . ?
C14 H14 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
C1 In1 C2 143.5(2) . . ?
C1 In1 O1 103.45(19) . . ?
C2 In1 O1 108.3(2) . . ?
C1 In1 N1 103.16(19) . . ?
C2 In1 N1 103.9(2) . . ?
O1 In1 N1 70.98(15) . . ?
C1 In1 O1 87.56(19) . 5_676 ?
C2 In1 O1 87.8(2) . 5_676 ?
O1 In1 O1 68.22(15) . 5_676 ?
N1 In1 O1 139.19(15) . 5_676 ?
C1 In1 N2 84.6(2) . . ?
C2 In1 N2 85.4(2) . . ?
O1 In1 N2 135.31(15) . . ?
N1 In1 N2 64.41(16) . . ?
O1 In1 N2 156.39(13) 5_676 . ?
C3 O1 In1 120.5(3) . . ?
C3 O1 In1 127.6(3) . 5_676 ?
In1 O1 In1 111.78(15) . 5_676 ?
C9 N1 C8 123.1(5) . . ?
C9 N1 In1 123.8(4) . . ?
C8 N1 In1 113.0(3) . . ?
C14 N2 C10 117.8(5) . . ?
C14 N2 In1 129.3(4) . . ?
C10 N2 In1 112.8(3) . . ?
In1 C1 H1A 109.5 . . ?
In1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
In1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
In1 C2 H2A 109.5 . . ?
In1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
In1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O1 C3 C4 121.8(5) . . ?
O1 C3 C8 121.1(5) . . ?
C4 C3 C8 117.2(5) . . ?
C5 C4 C3 121.4(5) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 120.6(5) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 119.8(5) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 120.9(5) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
N1 C8 C7 125.5(5) . . ?
N1 C8 C3 114.3(5) . . ?
C7 C8 C3 120.1(5) . . ?
N1 C9 C10 121.8(5) . . ?
N1 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
N2 C10 C11 122.7(5) . . ?
N2 C10 C9 117.0(5) . . ?
C11 C10 C9 120.3(5) . . ?
C12 C11 C10 118.9(6) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C13 C12 C11 118.6(5) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C12 C13 C14 118.2(5) . . ?
C12 C13 H13 120.9 . . ?
C14 C13 H13 120.9 . . ?
N2 C14 C13 123.8(6) . . ?
N2 C14 H14 118.1 . . ?
C13 C14 H14 118.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
In1 O1 C3 C4 -177.4(4) . . . . ?
In1 O1 C3 C4 -1.6(8) 5_676 . . . ?
In1 O1 C3 C8 0.8(7) . . . . ?
In1 O1 C3 C8 176.6(4) 5_676 . . . ?
O1 C3 C4 C5 177.7(6) . . . . ?
C8 C3 C4 C5 -0.5(9) . . . . ?
C3 C4 C5 C6 -0.9(9) . . . . ?
C4 C5 C6 C7 1.7(10) . . . . ?
C5 C6 C7 C8 -1.0(10) . . . . ?
C9 N1 C8 C7 -8.2(9) . . . . ?
In1 N1 C8 C7 175.5(5) . . . . ?
C9 N1 C8 C3 172.2(5) . . . . ?
In1 N1 C8 C3 -4.1(6) . . . . ?
C6 C7 C8 N1 180.0(6) . . . . ?
C6 C7 C8 C3 -0.5(9) . . . . ?
O1 C3 C8 N1 2.5(8) . . . . ?
C4 C3 C8 N1 -179.2(5) . . . . ?
O1 C3 C8 C7 -177.1(5) . . . . ?
C4 C3 C8 C7 1.2(9) . . . . ?
C8 N1 C9 C10 179.1(5) . . . . ?
In1 N1 C9 C10 -5.0(8) . . . . ?
C14 N2 C10 C11 -0.5(9) . . . . ?
In1 N2 C10 C11 -177.4(4) . . . . ?
C14 N2 C10 C9 179.5(5) . . . . ?
In1 N2 C10 C9 2.5(6) . . . . ?
N1 C9 C10 N2 1.1(8) . . . . ?
N1 C9 C10 C11 -178.9(6) . . . . ?
N2 C10 C11 C12 -0.5(9) . . . . ?
C9 C10 C11 C12 179.5(6) . . . . ?
C10 C11 C12 C13 1.2(9) . . . . ?
C11 C12 C13 C14 -0.7(9) . . . . ?
C10 N2 C14 C13 1.0(9) . . . . ?
In1 N2 C14 C13 177.3(5) . . . . ?
C12 C13 C14 N2 -0.4(10) . . . . ?

_refine_diff_density_max         1.562
_refine_diff_density_min         -1.352
_refine_diff_density_rms         0.249



####################################################################### 
# 
# 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_ersh14
_database_code_depnum_ccdc_archive 'CCDC 2361581'
loop_
_audit_author_name
_audit_author_address
'Ilya Yakushev'
;Kurnakov Institute of general and inorganic chemistry, RAS
Russia
;
_audit_update_record             
;
2024-06-10 deposited with the CCDC.	2025-02-18 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         'C28 H28 In2 N6 O6'
_chemical_formula_sum            'C28 H28 In2 N6 O6'
_chemical_formula_weight         774.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0027 0.0018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
In In -0.5973 1.4575 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0071 0.0037 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0124 0.0069 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.9004(19)
_cell_length_b                   8.4003(17)
_cell_length_c                   11.382(3)
_cell_angle_alpha                77.261(5)
_cell_angle_beta                 82.036(18)
_cell_angle_gamma                89.638(19)
_cell_volume                     729.4(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2060
_cell_measurement_theta_min      1.962
_cell_measurement_theta_max      26.960

_exptl_crystal_description       nugget
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.762
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.893
_shelx_estimated_absorpt_T_min   0.895
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.001
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'XDS (Kabsch, 2010)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.75268
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       φ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5470
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.962
_diffrn_reflns_theta_max         26.960
_diffrn_reflns_theta_full        26.847
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measured_fraction_theta_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 0.955
_reflns_number_total             2549
_reflns_number_gt                2240
_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       'Marccd (Doyle, 2011)'
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_reduction        XDS
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0358P)²+2.1340P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         2549
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.0924
_refine_ls_wR_factor_gt          0.0888
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
In1 In 0.48394(5) 0.71031(4) 0.37604(3) 0.02615(13) Uani 1 1 d . . . . .
O1 O 0.3847(4) 0.4525(4) 0.4310(3) 0.0290(8) Uani 1 1 d . . . . .
O2 O -0.1128(6) 0.3296(6) 0.0820(4) 0.0450(10) Uani 1 1 d . . . . .
O3 O -0.0895(5) 0.0827(5) 0.1852(4) 0.0392(9) Uani 1 1 d . . . . .
N1 N 0.2872(5) 0.6691(5) 0.2440(4) 0.0244(8) Uani 1 1 d . . . . .
N2 N 0.4353(5) 0.9694(6) 0.2137(4) 0.0290(9) Uani 1 1 d . . . . .
N3 N -0.0567(6) 0.2306(6) 0.1650(4) 0.0339(10) Uani 1 1 d . . . . .
C1 C 0.7359(7) 0.6862(7) 0.2835(5) 0.0323(12) Uani 1 1 d . . . . .
H1A H 0.770147 0.787501 0.223430 0.048 Uiso 1 1 calc R U . . .
H1B H 0.735434 0.595439 0.242232 0.048 Uiso 1 1 calc R U . . .
H1C H 0.816848 0.664611 0.342716 0.048 Uiso 1 1 calc R U . . .
C2 C 0.3256(7) 0.8079(7) 0.5100(5) 0.0337(12) Uani 1 1 d . . . . .
H2A H 0.302379 0.724054 0.585549 0.051 Uiso 1 1 calc R U . . .
H2B H 0.217469 0.842322 0.480317 0.051 Uiso 1 1 calc R U . . .
H2C H 0.384218 0.902087 0.525450 0.051 Uiso 1 1 calc R U . . .
C3 C 0.2761(6) 0.4013(6) 0.3720(4) 0.0257(10) Uani 1 1 d . . . . .
C4 C 0.2105(6) 0.2387(6) 0.4037(5) 0.0286(11) Uani 1 1 d . . . . .
H4 H 0.243801 0.165878 0.472681 0.034 Uiso 1 1 calc R U . . .
C5 C 0.1014(6) 0.1838(7) 0.3383(5) 0.0288(11) Uani 1 1 d . . . . .
H5 H 0.060106 0.073734 0.360349 0.035 Uiso 1 1 calc R U . . .
C6 C 0.0511(6) 0.2915(7) 0.2383(5) 0.0289(11) Uani 1 1 d . . . . .
C7 C 0.1056(6) 0.4530(7) 0.2044(4) 0.0277(11) Uani 1 1 d . . . . .
H7 H 0.066673 0.524246 0.136968 0.033 Uiso 1 1 calc R U . . .
C8 C 0.2178(6) 0.5099(6) 0.2700(4) 0.0270(10) Uani 1 1 d . . . . .
C9 C 0.2468(7) 0.7850(7) 0.1596(4) 0.0290(11) Uani 1 1 d . . . . .
H9 H 0.165125 0.764503 0.110464 0.035 Uiso 1 1 calc R U . . .
C10 C 0.3236(6) 0.9467(6) 0.1379(4) 0.0268(10) Uani 1 1 d . . . . .
C11 C 0.2846(6) 1.0722(6) 0.0438(4) 0.0272(10) Uani 1 1 d . . . . .
H11 H 0.206412 1.053567 -0.008310 0.033 Uiso 1 1 calc R U . . .
C12 C 0.3620(7) 1.2252(7) 0.0275(5) 0.0327(11) Uani 1 1 d . . . . .
H12 H 0.337841 1.312601 -0.036134 0.039 Uiso 1 1 calc R U . . .
C13 C 0.4744(7) 1.2480(7) 0.1053(5) 0.0323(11) Uani 1 1 d . . . . .
H13 H 0.528075 1.351647 0.096751 0.039 Uiso 1 1 calc R U . . .
C14 C 0.5074(6) 1.1168(6) 0.1963(5) 0.0279(10) Uani 1 1 d . . . . .
H14 H 0.585843 1.133054 0.249024 0.033 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 C2 2.138(5) . ?
In1 C1 2.149(5) . ?
In1 O1 2.232(4) . ?
In1 N1 2.383(4) . ?
In1 N2 2.591(4) . ?
In1 O1 2.657(3) 2_666 ?
O1 C3 1.290(6) . ?
O2 N3 1.243(6) . ?
O3 N3 1.235(6) . ?
N1 C9 1.281(7) . ?
N1 C8 1.402(7) . ?
N2 C14 1.329(7) . ?
N2 C10 1.358(6) . ?
N3 C6 1.440(7) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.416(8) . ?
C3 C8 1.438(7) . ?
C4 C5 1.358(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.381(8) . ?
C7 C8 1.385(7) . ?
C7 H7 0.9500 . ?
C9 C10 1.448(8) . ?
C9 H9 0.9500 . ?
C10 C11 1.394(7) . ?
C11 C12 1.390(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.380(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.387(7) . ?
C13 H13 0.9500 . ?
C14 H14 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
C2 In1 C1 148.2(2) . . ?
C2 In1 O1 98.64(19) . . ?
C1 In1 O1 102.57(18) . . ?
C2 In1 N1 102.38(17) . . ?
C1 In1 N1 106.83(17) . . ?
O1 In1 N1 70.80(13) . . ?
C2 In1 N2 89.32(17) . . ?
C1 In1 N2 91.11(17) . . ?
O1 In1 N2 136.91(13) . . ?
N1 In1 N2 66.13(14) . . ?
C2 In1 O1 82.71(16) . 2_666 ?
C1 In1 O1 83.12(16) . 2_666 ?
O1 In1 O1 68.96(13) . 2_666 ?
N1 In1 O1 139.74(13) . 2_666 ?
N2 In1 O1 154.02(13) . 2_666 ?
C3 O1 In1 120.4(3) . . ?
C3 O1 In1 128.5(3) . 2_666 ?
In1 O1 In1 111.04(13) . 2_666 ?
C9 N1 C8 124.1(4) . . ?
C9 N1 In1 122.0(4) . . ?
C8 N1 In1 113.9(3) . . ?
C14 N2 C10 118.0(4) . . ?
C14 N2 In1 127.8(3) . . ?
C10 N2 In1 114.2(3) . . ?
O3 N3 O2 122.0(4) . . ?
O3 N3 C6 119.6(4) . . ?
O2 N3 C6 118.5(5) . . ?
In1 C1 H1A 109.5 . . ?
In1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
In1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
In1 C2 H2A 109.5 . . ?
In1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
In1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O1 C3 C4 122.2(4) . . ?
O1 C3 C8 120.2(5) . . ?
C4 C3 C8 117.6(4) . . ?
C5 C4 C3 121.8(5) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 118.9(5) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C7 C6 C5 122.4(5) . . ?
C7 C6 N3 118.8(5) . . ?
C5 C6 N3 118.7(5) . . ?
C6 C7 C8 119.1(5) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C7 C8 N1 125.3(4) . . ?
C7 C8 C3 120.1(5) . . ?
N1 C8 C3 114.6(4) . . ?
N1 C9 C10 121.1(5) . . ?
N1 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
N2 C10 C11 121.9(5) . . ?
N2 C10 C9 116.6(4) . . ?
C11 C10 C9 121.5(4) . . ?
C12 C11 C10 118.9(5) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C13 C12 C11 118.9(5) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C12 C13 C14 118.7(5) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 H13 120.7 . . ?
N2 C14 C13 123.5(5) . . ?
N2 C14 H14 118.3 . . ?
C13 C14 H14 118.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
In1 O1 C3 C4 179.8(3) . . . . ?
In1 O1 C3 C4 -1.3(6) 2_666 . . . ?
In1 O1 C3 C8 0.1(6) . . . . ?
In1 O1 C3 C8 179.0(3) 2_666 . . . ?
O1 C3 C4 C5 -177.3(4) . . . . ?
C8 C3 C4 C5 2.4(7) . . . . ?
C3 C4 C5 C6 -0.9(7) . . . . ?
C4 C5 C6 C7 -1.2(7) . . . . ?
C4 C5 C6 N3 176.5(4) . . . . ?
O3 N3 C6 C7 171.3(4) . . . . ?
O2 N3 C6 C7 -8.1(7) . . . . ?
O3 N3 C6 C5 -6.5(7) . . . . ?
O2 N3 C6 C5 174.1(4) . . . . ?
C5 C6 C7 C8 1.6(7) . . . . ?
N3 C6 C7 C8 -176.0(4) . . . . ?
C6 C7 C8 N1 178.1(4) . . . . ?
C6 C7 C8 C3 0.0(7) . . . . ?
C9 N1 C8 C7 4.3(7) . . . . ?
In1 N1 C8 C7 -177.6(4) . . . . ?
C9 N1 C8 C3 -177.4(4) . . . . ?
In1 N1 C8 C3 0.7(5) . . . . ?
O1 C3 C8 C7 177.8(4) . . . . ?
C4 C3 C8 C7 -1.9(7) . . . . ?
O1 C3 C8 N1 -0.5(6) . . . . ?
C4 C3 C8 N1 179.8(4) . . . . ?
C8 N1 C9 C10 179.9(4) . . . . ?
In1 N1 C9 C10 2.0(6) . . . . ?
C14 N2 C10 C11 0.3(7) . . . . ?
In1 N2 C10 C11 -178.9(3) . . . . ?
C14 N2 C10 C9 -179.8(4) . . . . ?
In1 N2 C10 C9 1.1(5) . . . . ?
N1 C9 C10 N2 -2.0(7) . . . . ?
N1 C9 C10 C11 177.9(4) . . . . ?
N2 C10 C11 C12 -0.2(7) . . . . ?
C9 C10 C11 C12 179.8(4) . . . . ?
C10 C11 C12 C13 -0.3(7) . . . . ?
C11 C12 C13 C14 0.7(7) . . . . ?
C10 N2 C14 C13 0.1(7) . . . . ?
In1 N2 C14 C13 179.2(3) . . . . ?
C12 C13 C14 N2 -0.6(7) . . . . ?

_refine_diff_density_max         1.325
_refine_diff_density_min         -1.169
_refine_diff_density_rms         0.114



####################################################################### 
# 
# 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_23ersh12
_database_code_depnum_ccdc_archive 'CCDC 2361579'
loop_
_audit_author_name
_audit_author_address
'Ilya Yakushev'
;Kurnakov Institute of general and inorganic chemistry, RAS
Russia
;
_audit_update_record             
;
2024-06-10 deposited with the CCDC.	2025-02-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H34 In2 N4 O2'
_chemical_formula_sum            'C30 H34 In2 N4 O2'
_chemical_formula_weight         712.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
In In -0.7276 1.3100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.6219(5)
_cell_length_b                   17.4483(11)
_cell_length_c                   9.7888(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.362(2)
_cell_angle_gamma                90
_cell_volume                     1438.46(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7086
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      30.42

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.636
_shelx_estimated_absorpt_T_min   0.791
_shelx_estimated_absorpt_T_max   0.828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6225
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21821
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.335
_diffrn_reflns_theta_max         30.532
_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             4391
_reflns_number_gt                3456
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHERLXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0189P)²+0.6041P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         4391
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0635
_refine_ls_wR_factor_gt          0.0571
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
In1 In 0.69471(2) 0.54160(2) 0.61142(2) 0.01678(6) Uani 1 1 d . . . . .
O1 O 0.4403(2) 0.56588(9) 0.53898(19) 0.0200(4) Uani 1 1 d . . . . .
N1 N 0.6477(2) 0.67325(11) 0.6608(2) 0.0150(4) Uani 1 1 d . . . . .
N2 N 0.9457(3) 0.61752(12) 0.7634(2) 0.0212(5) Uani 1 1 d . . . . .
C1 C 0.8022(3) 0.56610(15) 0.4377(3) 0.0232(6) Uani 1 1 d . . . . .
H1A H 0.865089 0.613194 0.456560 0.035 Uiso 1 1 calc R U . . .
H1B H 0.719154 0.572828 0.352976 0.035 Uiso 1 1 calc R U . . .
H1C H 0.871434 0.523463 0.424347 0.035 Uiso 1 1 calc R U . . .
C2 C 0.7020(4) 0.46855(15) 0.7898(3) 0.0282(6) Uani 1 1 d . . . . .
H2A H 0.678436 0.415703 0.758199 0.042 Uiso 1 1 calc R U . . .
H2B H 0.622988 0.485909 0.841509 0.042 Uiso 1 1 calc R U . . .
H2C H 0.808040 0.470776 0.850884 0.042 Uiso 1 1 calc R U . . .
C3 C 0.4889(3) 0.69596(13) 0.6084(3) 0.0155(5) Uani 1 1 d . . . . .
C4 C 0.4320(3) 0.77095(13) 0.6124(3) 0.0167(5) Uani 1 1 d . . . . .
H4 H 0.502140 0.810066 0.655952 0.020 Uiso 1 1 calc R U . . .
C5 C 0.2754(3) 0.78918(14) 0.5540(3) 0.0191(5) Uani 1 1 d . . . . .
C6 C 0.1743(3) 0.72945(14) 0.4955(3) 0.0199(5) Uani 1 1 d . . . . .
H6 H 0.065868 0.740519 0.456902 0.024 Uiso 1 1 calc R U . . .
C7 C 0.2271(3) 0.65523(14) 0.4921(3) 0.0192(5) Uani 1 1 d . . . . .
H7 H 0.154579 0.616227 0.452067 0.023 Uiso 1 1 calc R U . . .
C8 C 0.3869(3) 0.63617(13) 0.5471(3) 0.0164(5) Uani 1 1 d . . . . .
C9 C 0.2141(3) 0.87013(15) 0.5503(3) 0.0264(6) Uani 1 1 d . . . . .
H9A H 0.185060 0.887783 0.453119 0.040 Uiso 1 1 calc R U . . .
H9B H 0.296803 0.903539 0.603403 0.040 Uiso 1 1 calc R U . . .
H9C H 0.120387 0.871739 0.591966 0.040 Uiso 1 1 calc R U . . .
C10 C 0.7607(3) 0.72076(14) 0.7048(3) 0.0170(5) Uani 1 1 d . . . . .
H10 H 0.738895 0.774174 0.702076 0.020 Uiso 1 1 calc R U . . .
C11 C 0.9231(3) 0.69378(14) 0.7591(3) 0.0172(5) Uani 1 1 d . . . . .
C12 C 1.0457(3) 0.74572(15) 0.8041(3) 0.0207(5) Uani 1 1 d . . . . .
H12 H 1.025851 0.799318 0.798944 0.025 Uiso 1 1 calc R U . . .
C13 C 1.1970(3) 0.71791(16) 0.8564(3) 0.0244(6) Uani 1 1 d . . . . .
H13 H 1.282993 0.752095 0.888047 0.029 Uiso 1 1 calc R U . . .
C14 C 1.2209(3) 0.63999(17) 0.8618(3) 0.0279(6) Uani 1 1 d . . . . .
H14 H 1.323574 0.619346 0.897346 0.033 Uiso 1 1 calc R U . . .
C15 C 1.0923(3) 0.59204(16) 0.8144(3) 0.0271(6) Uani 1 1 d . . . . .
H15 H 1.109692 0.538246 0.818514 0.033 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 C1 2.146(3) . ?
In1 C2 2.152(3) . ?
In1 O1 2.1969(17) . ?
In1 N1 2.400(2) . ?
In1 O1 2.5112(17) 3_666 ?
In1 N2 2.697(2) . ?
O1 C8 1.318(3) . ?
N1 C10 1.281(3) . ?
N1 C3 1.412(3) . ?
N2 C15 1.332(3) . ?
N2 C11 1.344(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.401(3) . ?
C3 C8 1.413(3) . ?
C4 C5 1.386(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.400(4) . ?
C5 C9 1.506(3) . ?
C6 C7 1.375(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.408(3) . ?
C7 H7 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.465(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.390(3) . ?
C12 C13 1.384(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.374(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(4) . ?
C14 H14 0.9500 . ?
C15 H15 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
C1 In1 C2 144.89(11) . . ?
C1 In1 O1 106.04(9) . . ?
C2 In1 O1 103.30(10) . . ?
C1 In1 N1 95.11(9) . . ?
C2 In1 N1 112.36(9) . . ?
O1 In1 N1 71.37(6) . . ?
C1 In1 O1 84.78(8) . 3_666 ?
C2 In1 O1 87.87(9) . 3_666 ?
O1 In1 O1 69.47(7) . 3_666 ?
N1 In1 O1 139.11(6) . 3_666 ?
C1 In1 N2 84.69(9) . . ?
C2 In1 N2 87.86(9) . . ?
O1 In1 N2 135.33(6) . . ?
N1 In1 N2 64.45(7) . . ?
O1 In1 N2 155.07(6) 3_666 . ?
C8 O1 In1 119.82(15) . . ?
C8 O1 In1 127.30(15) . 3_666 ?
In1 O1 In1 110.53(7) . 3_666 ?
C10 N1 C3 123.3(2) . . ?
C10 N1 In1 122.55(16) . . ?
C3 N1 In1 112.81(14) . . ?
C15 N2 C11 117.5(2) . . ?
C15 N2 In1 128.89(18) . . ?
C11 N2 In1 112.04(15) . . ?
In1 C1 H1A 109.5 . . ?
In1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
In1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
In1 C2 H2A 109.5 . . ?
In1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
In1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 N1 124.8(2) . . ?
C4 C3 C8 120.8(2) . . ?
N1 C3 C8 114.5(2) . . ?
C5 C4 C3 121.3(2) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 117.7(2) . . ?
C4 C5 C9 122.1(2) . . ?
C6 C5 C9 120.3(2) . . ?
C7 C6 C5 122.0(2) . . ?
C7 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
C6 C7 C8 121.0(2) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
O1 C8 C7 121.5(2) . . ?
O1 C8 C3 121.3(2) . . ?
C7 C8 C3 117.2(2) . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 C11 120.8(2) . . ?
N1 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
N2 C11 C12 122.7(2) . . ?
N2 C11 C10 116.8(2) . . ?
C12 C11 C10 120.5(2) . . ?
C13 C12 C11 118.8(2) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C14 C13 C12 118.9(2) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C13 C14 C15 118.8(3) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
N2 C15 C14 123.4(3) . . ?
N2 C15 H15 118.3 . . ?
C14 C15 H15 118.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 N1 C3 C4 -7.5(4) . . . . ?
In1 N1 C3 C4 -174.5(2) . . . . ?
C10 N1 C3 C8 171.4(2) . . . . ?
In1 N1 C3 C8 4.5(3) . . . . ?
N1 C3 C4 C5 177.6(2) . . . . ?
C8 C3 C4 C5 -1.4(4) . . . . ?
C3 C4 C5 C6 2.4(4) . . . . ?
C3 C4 C5 C9 -176.7(2) . . . . ?
C4 C5 C6 C7 -1.5(4) . . . . ?
C9 C5 C6 C7 177.6(3) . . . . ?
C5 C6 C7 C8 -0.4(4) . . . . ?
In1 O1 C8 C7 175.09(19) . . . . ?
In1 O1 C8 C7 14.2(3) 3_666 . . . ?
In1 O1 C8 C3 -3.3(3) . . . . ?
In1 O1 C8 C3 -164.24(17) 3_666 . . . ?
C6 C7 C8 O1 -177.0(2) . . . . ?
C6 C7 C8 C3 1.5(4) . . . . ?
C4 C3 C8 O1 177.9(2) . . . . ?
N1 C3 C8 O1 -1.2(3) . . . . ?
C4 C3 C8 C7 -0.6(4) . . . . ?
N1 C3 C8 C7 -179.6(2) . . . . ?
C3 N1 C10 C11 179.5(2) . . . . ?
In1 N1 C10 C11 -14.8(3) . . . . ?
C15 N2 C11 C12 0.6(4) . . . . ?
In1 N2 C11 C12 -166.3(2) . . . . ?
C15 N2 C11 C10 -179.1(2) . . . . ?
In1 N2 C11 C10 14.0(3) . . . . ?
N1 C10 C11 N2 -1.6(4) . . . . ?
N1 C10 C11 C12 178.7(2) . . . . ?
N2 C11 C12 C13 -0.5(4) . . . . ?
C10 C11 C12 C13 179.2(2) . . . . ?
C11 C12 C13 C14 0.1(4) . . . . ?
C12 C13 C14 C15 0.1(4) . . . . ?
C11 N2 C15 C14 -0.4(4) . . . . ?
In1 N2 C15 C14 164.0(2) . . . . ?
C13 C14 C15 N2 0.0(5) . . . . ?

_refine_diff_density_max         0.618
_refine_diff_density_min         -0.676
_refine_diff_density_rms         0.119



####################################################################### 
# 
# 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_23ersh10
_database_code_depnum_ccdc_archive 'CCDC 2361580'
loop_
_audit_author_name
_audit_author_address
'Ilya Yakushev'
;Kurnakov Institute of general and inorganic chemistry, RAS
Russia
;
_audit_update_record             
;
2024-06-10 deposited with the CCDC.	2025-02-18 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         'C28 H28 Cl2 In2 N4 O2'
_chemical_formula_sum            'C28 H28 Cl2 In2 N4 O2'
_chemical_formula_weight         753.08

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
In In -0.7276 1.3100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.5866(2)
_cell_length_b                   17.1574(5)
_cell_length_c                   9.9567(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.3870(10)
_cell_angle_gamma                90
_cell_volume                     1432.71(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9858
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      30.50

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.746
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.829
_shelx_estimated_absorpt_T_min   0.668
_shelx_estimated_absorpt_T_max   0.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6196
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23889
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.374
_diffrn_reflns_theta_max         30.503
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4384
_reflns_number_gt                3841
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0145P)²+0.7106P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         4384
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0200
_refine_ls_wR_factor_ref         0.0484
_refine_ls_wR_factor_gt          0.0467
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
In1 In 0.30337(2) 0.45803(2) 0.38632(2) 0.02338(4) Uani 1 1 d . . . . .
Cl1 Cl 0.79677(6) 0.11379(3) 0.43755(5) 0.03905(11) Uani 1 1 d . . . . .
O1 O 0.55772(13) 0.43194(7) 0.46365(13) 0.0289(3) Uani 1 1 d . . . . .
N1 N 0.35052(15) 0.32391(7) 0.33977(13) 0.0205(2) Uani 1 1 d . . . . .
N2 N 0.05397(17) 0.38247(8) 0.23549(15) 0.0282(3) Uani 1 1 d . . . . .
C1 C 0.1932(2) 0.43383(11) 0.55704(19) 0.0293(3) Uani 1 1 d . . . . .
H1A H 0.125754 0.387403 0.536694 0.044 Uiso 1 1 calc R U . . .
H1B H 0.127684 0.478432 0.572065 0.044 Uiso 1 1 calc R U . . .
H1C H 0.276007 0.424653 0.639964 0.044 Uiso 1 1 calc R U . . .
C2 C 0.3002(3) 0.53188(11) 0.2120(2) 0.0393(4) Uani 1 1 d . . . . .
H2A H 0.346167 0.582697 0.243396 0.059 Uiso 1 1 calc R U . . .
H2B H 0.190046 0.538889 0.161204 0.059 Uiso 1 1 calc R U . . .
H2C H 0.363102 0.507809 0.151780 0.059 Uiso 1 1 calc R U . . .
C3 C 0.61146(18) 0.36106(9) 0.45458(16) 0.0225(3) Uani 1 1 d . . . . .
C4 C 0.77254(19) 0.34148(10) 0.50874(18) 0.0268(3) Uani 1 1 d . . . . .
H4 H 0.844690 0.381063 0.549614 0.032 Uiso 1 1 calc R U . . .
C5 C 0.82707(19) 0.26674(10) 0.50367(17) 0.0269(3) Uani 1 1 d . . . . .
H5 H 0.935572 0.254828 0.541912 0.032 Uiso 1 1 calc R U . . .
C6 C 0.7233(2) 0.20814(9) 0.44235(17) 0.0252(3) Uani 1 1 d . . . . .
C7 C 0.56586(19) 0.22418(9) 0.38496(16) 0.0229(3) Uani 1 1 d . . . . .
H7 H 0.496709 0.184096 0.341527 0.028 Uiso 1 1 calc R U . . .
C8 C 0.50909(17) 0.30019(9) 0.39142(15) 0.0199(3) Uani 1 1 d . . . . .
C9 C 0.23596(18) 0.27602(9) 0.29619(16) 0.0219(3) Uani 1 1 d . . . . .
H9 H 0.256303 0.221553 0.299800 0.026 Uiso 1 1 calc R U . . .
C10 C 0.07423(18) 0.30459(9) 0.24096(16) 0.0218(3) Uani 1 1 d . . . . .
C11 C -0.04990(19) 0.25274(10) 0.19563(17) 0.0260(3) Uani 1 1 d . . . . .
H11 H -0.032007 0.198082 0.201430 0.031 Uiso 1 1 calc R U . . .
C12 C -0.2004(2) 0.28228(12) 0.14178(18) 0.0325(4) Uani 1 1 d . . . . .
H12 H -0.287565 0.248115 0.110115 0.039 Uiso 1 1 calc R U . . .
C13 C -0.2220(2) 0.36149(13) 0.1347(2) 0.0378(4) Uani 1 1 d . . . . .
H13 H -0.323852 0.383128 0.097241 0.045 Uiso 1 1 calc R U . . .
C14 C -0.0915(2) 0.40953(11) 0.1836(2) 0.0359(4) Uani 1 1 d . . . . .
H14 H -0.107200 0.464359 0.179652 0.043 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 C2 2.1445(19) . ?
In1 C1 2.1556(18) . ?
In1 O1 2.2004(11) . ?
In1 N1 2.3988(13) . ?
In1 O1 2.5404(11) 3_666 ?
In1 N2 2.6725(14) . ?
Cl1 C6 1.7419(16) . ?
O1 C3 1.3106(19) . ?
N1 C9 1.2837(19) . ?
N1 C8 1.4084(19) . ?
N2 C14 1.329(2) . ?
N2 C10 1.347(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.413(2) . ?
C3 C8 1.422(2) . ?
C4 C5 1.370(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.394(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.378(2) . ?
C7 C8 1.398(2) . ?
C7 H7 0.9500 . ?
C9 C10 1.464(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.387(2) . ?
C11 C12 1.384(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.371(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.392(3) . ?
C13 H13 0.9500 . ?
C14 H14 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
C2 In1 C1 145.14(8) . . ?
C2 In1 O1 104.04(7) . . ?
C1 In1 O1 104.80(6) . . ?
C2 In1 N1 112.57(6) . . ?
C1 In1 N1 95.08(6) . . ?
O1 In1 N1 71.12(4) . . ?
C2 In1 O1 87.68(6) . 3_666 ?
C1 In1 O1 84.81(6) . 3_666 ?
O1 In1 O1 68.89(5) . 3_666 ?
N1 In1 O1 138.51(4) . 3_666 ?
C2 In1 N2 87.85(6) . . ?
C1 In1 N2 85.14(6) . . ?
O1 In1 N2 135.52(4) . . ?
N1 In1 N2 64.80(4) . . ?
O1 In1 N2 155.43(4) 3_666 . ?
C3 O1 In1 120.16(9) . . ?
C3 O1 In1 127.03(10) . 3_666 ?
In1 O1 In1 111.11(5) . 3_666 ?
C9 N1 C8 123.31(13) . . ?
C9 N1 In1 122.03(11) . . ?
C8 N1 In1 113.37(9) . . ?
C14 N2 C10 117.70(15) . . ?
C14 N2 In1 128.47(12) . . ?
C10 N2 In1 112.17(10) . . ?
In1 C1 H1A 109.5 . . ?
In1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
In1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
In1 C2 H2A 109.5 . . ?
In1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
In1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O1 C3 C4 121.64(14) . . ?
O1 C3 C8 121.24(14) . . ?
C4 C3 C8 117.12(14) . . ?
C5 C4 C3 121.52(15) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 119.97(15) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C7 C6 C5 121.05(15) . . ?
C7 C6 Cl1 120.22(13) . . ?
C5 C6 Cl1 118.73(13) . . ?
C6 C7 C8 119.20(14) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C7 C8 N1 124.89(13) . . ?
C7 C8 C3 121.11(14) . . ?
N1 C8 C3 114.00(13) . . ?
N1 C9 C10 120.60(14) . . ?
N1 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
N2 C10 C11 122.64(15) . . ?
N2 C10 C9 116.82(13) . . ?
C11 C10 C9 120.54(14) . . ?
C12 C11 C10 118.63(16) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
C13 C12 C11 119.17(16) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C14 118.62(17) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 H13 120.7 . . ?
N2 C14 C13 123.23(18) . . ?
N2 C14 H14 118.4 . . ?
C13 C14 H14 118.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
In1 O1 C3 C4 -177.10(12) . . . . ?
In1 O1 C3 C4 -13.4(2) 3_666 . . . ?
In1 O1 C3 C8 1.9(2) . . . . ?
In1 O1 C3 C8 165.67(11) 3_666 . . . ?
O1 C3 C4 C5 177.54(16) . . . . ?
C8 C3 C4 C5 -1.5(2) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
C4 C5 C6 C7 0.7(3) . . . . ?
C4 C5 C6 Cl1 179.92(13) . . . . ?
C5 C6 C7 C8 -1.5(2) . . . . ?
Cl1 C6 C7 C8 179.29(12) . . . . ?
C6 C7 C8 N1 -178.49(15) . . . . ?
C6 C7 C8 C3 0.8(2) . . . . ?
C9 N1 C8 C7 9.0(2) . . . . ?
In1 N1 C8 C7 176.30(12) . . . . ?
C9 N1 C8 C3 -170.26(15) . . . . ?
In1 N1 C8 C3 -3.00(16) . . . . ?
O1 C3 C8 C7 -178.37(15) . . . . ?
C4 C3 C8 C7 0.7(2) . . . . ?
O1 C3 C8 N1 1.0(2) . . . . ?
C4 C3 C8 N1 -179.97(14) . . . . ?
C8 N1 C9 C10 -178.68(14) . . . . ?
In1 N1 C9 C10 15.1(2) . . . . ?
C14 N2 C10 C11 -0.4(3) . . . . ?
In1 N2 C10 C11 166.22(12) . . . . ?
C14 N2 C10 C9 178.93(16) . . . . ?
In1 N2 C10 C9 -14.50(17) . . . . ?
N1 C9 C10 N2 1.6(2) . . . . ?
N1 C9 C10 C11 -179.11(15) . . . . ?
N2 C10 C11 C12 0.4(2) . . . . ?
C9 C10 C11 C12 -178.81(15) . . . . ?
C10 C11 C12 C13 0.1(3) . . . . ?
C11 C12 C13 C14 -0.7(3) . . . . ?
C10 N2 C14 C13 -0.3(3) . . . . ?
In1 N2 C14 C13 -164.35(15) . . . . ?
C12 C13 C14 N2 0.8(3) . . . . ?

_refine_diff_density_max         0.464
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.065



