# Supplementary Information (SI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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 2374055'
loop_
_audit_author_name
_audit_author_address
'Tarun Kanti Panda'
;IIT Hyderabad
India
;
_audit_update_record             
;
2024-07-28 deposited with the CCDC.	2024-11-11 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         'C23 H24 Cl3 In N2 O'
_chemical_formula_sum            'C23 H24 Cl3 In N2 O'
_chemical_formula_weight         565.61

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'
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'

_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                   8.8110(3)
_cell_length_b                   14.1384(5)
_cell_length_c                   19.8289(6)
_cell_angle_alpha                80.3650(10)
_cell_angle_beta                 87.6050(10)
_cell_angle_gamma                82.2660(10)
_cell_volume                     2412.69(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    48585
_cell_measurement_theta_min      2.084
_cell_measurement_theta_max      27.110

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_F_000             1136
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    1.329
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.76387
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Bruker (Mo) X-ray Source'
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48585
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.084
_diffrn_reflns_theta_max         27.110
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             10647
_reflns_number_gt                6628
_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       
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP 3.0 & Olex 2.1'
_computing_publication_material  WinGX
_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)+(0.0381P)²+0.9279P] 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         10647
_refine_ls_number_parameters     541
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.0968
_refine_ls_wR_factor_gt          0.0837
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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 0.55083(3) 0.12399(2) 0.68047(2) 0.04744(8) Uani 1 1 d . . . . .
In2 In 0.05274(3) 0.62707(2) 0.67535(2) 0.04827(9) Uani 1 1 d . . . . .
Cl1 Cl 0.56822(12) 0.29180(7) 0.68961(5) 0.0693(3) Uani 1 1 d . . . . .
Cl2 Cl 0.35500(11) 0.08120(8) 0.76358(5) 0.0727(3) Uani 1 1 d . . . . .
Cl3 Cl 0.40570(12) 0.15913(9) 0.57627(5) 0.0789(3) Uani 1 1 d . . . . .
Cl4 Cl 0.09100(13) 0.79361(7) 0.68080(6) 0.0748(3) Uani 1 1 d . . . . .
Cl5 Cl -0.14203(11) 0.60992(8) 0.76317(5) 0.0730(3) Uani 1 1 d . . . . .
Cl6 Cl -0.09532(12) 0.65736(10) 0.57231(5) 0.0870(4) Uani 1 1 d . . . . .
N1 N 0.7758(3) 0.11191(18) 0.61785(13) 0.0454(7) Uani 1 1 d . . . . .
N2 N 0.7500(3) 0.05997(18) 0.75572(13) 0.0444(6) Uani 1 1 d . . . . .
N3 N 0.2746(3) 0.60732(19) 0.60959(13) 0.0458(7) Uani 1 1 d . . . . .
N4 N 0.2574(3) 0.57454(18) 0.74783(12) 0.0437(6) Uani 1 1 d . . . . .
O2 O 0.0628(3) 0.46110(18) 0.67198(13) 0.0670(7) Uani 1 1 d . . . . .
O1 O 0.5844(4) -0.04063(19) 0.66433(14) 0.0777(8) Uani 1 1 d . . . . .
C1 C 0.7898(4) 0.1370(2) 0.55045(17) 0.0540(9) Uani 1 1 d . . . . .
H1 H 0.702428 0.162188 0.525420 0.065 Uiso 1 1 calc R U . . .
C2 C 0.9287(5) 0.1271(3) 0.51638(18) 0.0600(10) Uani 1 1 d . . . . .
H2 H 0.934550 0.144365 0.469068 0.072 Uiso 1 1 calc R U . . .
C3 C 1.0571(5) 0.0919(3) 0.5525(2) 0.0625(10) Uani 1 1 d . . . . .
H3 H 1.152390 0.085941 0.530508 0.075 Uiso 1 1 calc R U . . .
C4 C 1.0444(4) 0.0649(3) 0.62269(18) 0.0563(9) Uani 1 1 d . . . . .
H4 H 1.130841 0.039819 0.648385 0.068 Uiso 1 1 calc R U . . .
C5 C 0.9032(4) 0.0756(2) 0.65373(16) 0.0439(8) Uani 1 1 d . . . . .
C6 C 0.8809(4) 0.0478(2) 0.72773(16) 0.0486(8) Uani 1 1 d . . . . .
H6 H 0.964873 0.020717 0.754558 0.058 Uiso 1 1 calc R U . . .
C7 C 0.7256(4) 0.0271(2) 0.83024(15) 0.0492(8) Uani 1 1 d . . . . .
H7 H 0.638412 -0.009933 0.834331 0.059 Uiso 1 1 calc R U . . .
C8 C 0.6776(4) 0.1122(3) 0.86668(16) 0.0519(9) Uani 1 1 d . . . . .
C9 C 0.5778(5) 0.1009(3) 0.92272(18) 0.0717(11) Uani 1 1 d . . . . .
H9 H 0.534912 0.043647 0.934400 0.086 Uiso 1 1 calc R U . . .
C10 C 0.5420(6) 0.1735(4) 0.9609(2) 0.0936(16) Uani 1 1 d . . . . .
H10 H 0.476297 0.164420 0.998733 0.112 Uiso 1 1 calc R U . . .
C11 C 0.6019(6) 0.2592(4) 0.9442(2) 0.0853(14) Uani 1 1 d . . . . .
H11 H 0.577770 0.307910 0.970612 0.102 Uiso 1 1 calc R U . . .
C12 C 0.6965(6) 0.2722(3) 0.8887(2) 0.0831(13) Uani 1 1 d . . . . .
H12 H 0.735524 0.330707 0.876402 0.100 Uiso 1 1 calc R U . . .
C13 C 0.7361(5) 0.1984(3) 0.84986(19) 0.0671(11) Uani 1 1 d . . . . .
H13 H 0.802442 0.207860 0.812339 0.080 Uiso 1 1 calc R U . . .
C14 C 0.8587(4) -0.0411(3) 0.86422(16) 0.0542(9) Uani 1 1 d . . . . .
C15 C 0.9691(5) -0.0099(3) 0.8991(2) 0.0910(15) Uani 1 1 d . . . . .
H15 H 0.962983 0.055321 0.902501 0.109 Uiso 1 1 calc R U . . .
C16 C 1.0887(6) -0.0741(5) 0.9292(3) 0.116(2) Uani 1 1 d . . . . .
H16 H 1.163050 -0.051848 0.952224 0.139 Uiso 1 1 calc R U . . .
C17 C 1.0982(7) -0.1700(5) 0.9252(2) 0.1047(19) Uani 1 1 d . . . . .
H17 H 1.177876 -0.213601 0.946069 0.126 Uiso 1 1 calc R U . . .
C18 C 0.9923(7) -0.2008(3) 0.8912(3) 0.0995(17) Uani 1 1 d . . . . .
H18 H 0.999755 -0.266180 0.887992 0.119 Uiso 1 1 calc R U . . .
C19 C 0.8713(5) -0.1378(3) 0.8605(2) 0.0741(12) Uani 1 1 d . . . . .
H19 H 0.798402 -0.161145 0.837341 0.089 Uiso 1 1 calc R U . . .
C20 C 0.5593(11) -0.1183(4) 0.7092(3) 0.210(5) Uani 1 1 d . . . . .
H20A H 0.472102 -0.100994 0.738224 0.252 Uiso 1 1 calc R U . . .
H20B H 0.647778 -0.138287 0.738090 0.252 Uiso 1 1 calc R U . . .
C21 C 0.5305(7) -0.1975(4) 0.6781(2) 0.1027(17) Uani 1 1 d . . . . .
H21A H 0.433003 -0.218749 0.693823 0.123 Uiso 1 1 calc R U . . .
H21B H 0.610993 -0.251536 0.688180 0.123 Uiso 1 1 calc R U . . .
C22 C 0.5282(8) -0.1596(4) 0.6067(2) 0.133(3) Uani 1 1 d . . . . .
H22A H 0.424209 -0.139219 0.591174 0.160 Uiso 1 1 calc R U . . .
H22B H 0.577948 -0.206989 0.580023 0.160 Uiso 1 1 calc R U . . .
C23 C 0.6137(9) -0.0774(4) 0.6021(3) 0.161(3) Uani 1 1 d . . . . .
H23A H 0.722363 -0.097607 0.596216 0.193 Uiso 1 1 calc R U . . .
H23B H 0.579760 -0.028255 0.563545 0.193 Uiso 1 1 calc R U . . .
C24 C 0.4052(4) 0.5817(2) 0.64446(16) 0.0441(8) Uani 1 1 d . . . . .
C25 C 0.3885(4) 0.5665(2) 0.71940(16) 0.0475(8) Uani 1 1 d . . . . .
H25 H 0.475260 0.550678 0.746178 0.057 Uiso 1 1 calc R U . . .
C26 C 0.2386(4) 0.5648(2) 0.82338(16) 0.0488(8) Uani 1 1 d . . . . .
H26 H 0.149735 0.611158 0.832078 0.059 Uiso 1 1 calc R U . . .
C27 C 0.1981(4) 0.4658(2) 0.85355(16) 0.0511(9) Uani 1 1 d . . . . .
C28 C 0.2687(5) 0.3823(3) 0.83256(19) 0.0659(11) Uani 1 1 d . . . . .
H28 H 0.342481 0.386028 0.797612 0.079 Uiso 1 1 calc R U . . .
C29 C 0.2305(5) 0.2927(3) 0.8633(2) 0.0800(13) Uani 1 1 d . . . . .
H29 H 0.277649 0.236717 0.848405 0.096 Uiso 1 1 calc R U . . .
C30 C 0.1241(6) 0.2866(4) 0.9151(3) 0.0915(15) Uani 1 1 d . . . . .
H30 H 0.099605 0.226518 0.935959 0.110 Uiso 1 1 calc R U . . .
C31 C 0.0530(6) 0.3691(4) 0.9364(2) 0.0918(15) Uani 1 1 d . . . . .
H31 H -0.020165 0.365157 0.971610 0.110 Uiso 1 1 calc R U . . .
C32 C 0.0906(5) 0.4578(3) 0.90541(19) 0.0713(11) Uani 1 1 d . . . . .
H32 H 0.041916 0.513545 0.920049 0.086 Uiso 1 1 calc R U . . .
C33 C 0.3744(4) 0.5944(3) 0.85633(16) 0.0515(9) Uani 1 1 d . . . . .
C34 C 0.3935(5) 0.6909(3) 0.84746(18) 0.0643(10) Uani 1 1 d . . . . .
H34 H 0.323192 0.736437 0.821916 0.077 Uiso 1 1 calc R U . . .
C35 C 0.5155(5) 0.7210(3) 0.8759(2) 0.0778(13) Uani 1 1 d . . . . .
H35 H 0.525996 0.786513 0.869765 0.093 Uiso 1 1 calc R U . . .
C36 C 0.6209(5) 0.6551(4) 0.9131(2) 0.0826(13) Uani 1 1 d . . . . .
H36 H 0.703439 0.675378 0.931952 0.099 Uiso 1 1 calc R U . . .
C37 C 0.6037(5) 0.5595(4) 0.9223(2) 0.0858(13) Uani 1 1 d . . . . .
H37 H 0.675183 0.514356 0.947547 0.103 Uiso 1 1 calc R U . . .
C38 C 0.4803(5) 0.5285(3) 0.8945(2) 0.0697(11) Uani 1 1 d . . . . .
H38 H 0.469376 0.463030 0.901645 0.084 Uiso 1 1 calc R U . . .
C39 C 0.5456(4) 0.5767(3) 0.61246(18) 0.0541(9) Uani 1 1 d . . . . .
H39 H 0.634341 0.558890 0.637819 0.065 Uiso 1 1 calc R U . . .
C40 C 0.5542(4) 0.5982(3) 0.54198(18) 0.0582(10) Uani 1 1 d . . . . .
H40 H 0.648657 0.595243 0.519158 0.070 Uiso 1 1 calc R U . . .
C41 C 0.4214(5) 0.6241(2) 0.50633(18) 0.0559(9) Uani 1 1 d . . . . .
H41 H 0.424299 0.639281 0.458854 0.067 Uiso 1 1 calc R U . . .
C42 C 0.2837(4) 0.6273(2) 0.54162(17) 0.0532(9) Uani 1 1 d . . . . .
H42 H 0.193592 0.644139 0.517135 0.064 Uiso 1 1 calc R U . . .
C43 C -0.0336(5) 0.3987(3) 0.7133(2) 0.0779(12) Uani 1 1 d . . . . .
H43A H -0.141005 0.421969 0.705264 0.093 Uiso 1 1 calc R U . . .
H43B H -0.013912 0.394341 0.761548 0.093 Uiso 1 1 calc R U . . .
C44 C 0.0095(6) 0.3028(3) 0.6906(3) 0.0954(15) Uani 1 1 d . . . . .
H44A H 0.097506 0.266625 0.715088 0.114 Uiso 1 1 calc R U . . .
H44B H -0.075112 0.264582 0.697471 0.114 Uiso 1 1 calc R U . . .
C45 C 0.0454(7) 0.3281(4) 0.6191(3) 0.116(2) Uani 1 1 d . . . . .
H45A H -0.046872 0.342554 0.592296 0.140 Uiso 1 1 calc R U . . .
H45B H 0.112421 0.276278 0.602624 0.140 Uiso 1 1 calc R U . . .
C46 C 0.1242(7) 0.4159(3) 0.6160(3) 0.115(2) Uani 1 1 d . . . . .
H46A H 0.233997 0.398005 0.620266 0.137 Uiso 1 1 calc R U . . .
H46B H 0.104163 0.459216 0.573041 0.137 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 2.297(3) . ?
In1 N2 2.338(3) . ?
In1 O1 2.380(3) . ?
In1 Cl2 2.4017(10) . ?
In1 Cl3 2.4202(9) . ?
In1 Cl1 2.4349(10) . ?
In2 N3 2.315(3) . ?
In2 N4 2.317(3) . ?
In2 O2 2.348(2) . ?
In2 Cl5 2.3994(9) . ?
In2 Cl6 2.4165(10) . ?
In2 Cl4 2.4436(10) . ?
N1 C1 1.329(4) . ?
N1 C5 1.348(4) . ?
N2 C6 1.263(4) . ?
N2 C7 1.489(4) . ?
N3 C42 1.331(4) . ?
N3 C24 1.343(4) . ?
N4 C25 1.264(4) . ?
N4 C26 1.486(4) . ?
O2 C46 1.423(5) . ?
O2 C43 1.440(4) . ?
O1 C20 1.329(5) . ?
O1 C23 1.418(5) . ?
C1 C2 1.375(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.356(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.366(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.466(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.509(5) . ?
C7 C14 1.517(5) . ?
C7 H7 0.9800 . ?
C8 C13 1.371(5) . ?
C8 C9 1.389(5) . ?
C9 C10 1.371(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.371(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.355(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.397(5) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C19 1.372(5) . ?
C14 C15 1.375(5) . ?
C15 C16 1.380(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.363(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.333(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.385(6) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.421(6) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.428(6) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.457(7) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C39 1.365(4) . ?
C24 C25 1.469(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.511(4) . ?
C26 C33 1.524(4) . ?
C26 H26 0.9800 . ?
C27 C32 1.369(5) . ?
C27 C28 1.378(5) . ?
C28 C29 1.389(5) . ?
C28 H28 0.9300 . ?
C29 C30 1.361(6) . ?
C29 H29 0.9300 . ?
C30 C31 1.370(6) . ?
C30 H30 0.9300 . ?
C31 C32 1.378(5) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C33 C34 1.378(5) . ?
C33 C38 1.379(5) . ?
C34 C35 1.383(5) . ?
C34 H34 0.9300 . ?
C35 C36 1.367(6) . ?
C35 H35 0.9300 . ?
C36 C37 1.362(6) . ?
C36 H36 0.9300 . ?
C37 C38 1.392(5) . ?
C37 H37 0.9300 . ?
C38 H38 0.9300 . ?
C39 C40 1.381(5) . ?
C39 H39 0.9300 . ?
C40 C41 1.367(5) . ?
C40 H40 0.9300 . ?
C41 C42 1.375(5) . ?
C41 H41 0.9300 . ?
C42 H42 0.9300 . ?
C43 C44 1.496(6) . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C44 C45 1.434(6) . ?
C44 H44A 0.9700 . ?
C44 H44B 0.9700 . ?
C45 C46 1.494(6) . ?
C45 H45A 0.9700 . ?
C45 H45B 0.9700 . ?
C46 H46A 0.9700 . ?
C46 H46B 0.9700 . ?

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 N2 71.80(9) . . ?
N1 In1 O1 77.27(10) . . ?
N2 In1 O1 79.38(9) . . ?
N1 In1 Cl2 159.91(7) . . ?
N2 In1 Cl2 93.48(7) . . ?
O1 In1 Cl2 86.79(8) . . ?
N1 In1 Cl3 90.43(7) . . ?
N2 In1 Cl3 159.46(7) . . ?
O1 In1 Cl3 86.85(8) . . ?
Cl2 In1 Cl3 100.94(4) . . ?
N1 In1 Cl1 91.93(7) . . ?
N2 In1 Cl1 94.83(7) . . ?
O1 In1 Cl1 168.87(8) . . ?
Cl2 In1 Cl1 103.16(4) . . ?
Cl3 In1 Cl1 96.02(4) . . ?
N3 In2 N4 71.43(9) . . ?
N3 In2 O2 81.54(9) . . ?
N4 In2 O2 82.90(9) . . ?
N3 In2 Cl5 164.34(7) . . ?
N4 In2 Cl5 95.63(7) . . ?
O2 In2 Cl5 88.27(7) . . ?
N3 In2 Cl6 89.36(7) . . ?
N4 In2 Cl6 159.62(7) . . ?
O2 In2 Cl6 87.71(7) . . ?
Cl5 In2 Cl6 102.15(4) . . ?
N3 In2 Cl4 90.62(7) . . ?
N4 In2 Cl4 88.65(7) . . ?
O2 In2 Cl4 169.94(7) . . ?
Cl5 In2 Cl4 98.01(4) . . ?
Cl6 In2 Cl4 98.56(4) . . ?
C1 N1 C5 118.4(3) . . ?
C1 N1 In1 125.7(2) . . ?
C5 N1 In1 115.9(2) . . ?
C6 N2 C7 121.4(3) . . ?
C6 N2 In1 114.9(2) . . ?
C7 N2 In1 123.5(2) . . ?
C42 N3 C24 118.4(3) . . ?
C42 N3 In2 125.6(2) . . ?
C24 N3 In2 115.7(2) . . ?
C25 N4 C26 121.4(3) . . ?
C25 N4 In2 116.0(2) . . ?
C26 N4 In2 122.0(2) . . ?
C46 O2 C43 108.8(3) . . ?
C46 O2 In2 124.2(2) . . ?
C43 O2 In2 124.0(2) . . ?
C20 O1 C23 103.4(4) . . ?
C20 O1 In1 128.2(3) . . ?
C23 O1 In1 127.8(3) . . ?
N1 C1 C2 122.4(3) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C3 C2 C1 119.2(3) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 119.0(3) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 119.2(3) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
N1 C5 C4 121.8(3) . . ?
N1 C5 C6 116.1(3) . . ?
C4 C5 C6 122.1(3) . . ?
N2 C6 C5 121.2(3) . . ?
N2 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
N2 C7 C8 110.8(3) . . ?
N2 C7 C14 114.1(3) . . ?
C8 C7 C14 112.6(3) . . ?
N2 C7 H7 106.2 . . ?
C8 C7 H7 106.2 . . ?
C14 C7 H7 106.2 . . ?
C13 C8 C9 118.2(4) . . ?
C13 C8 C7 122.9(3) . . ?
C9 C8 C7 118.7(3) . . ?
C10 C9 C8 120.6(4) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 120.9(4) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 119.2(4) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C11 C12 C13 120.7(4) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C8 C13 C12 120.4(4) . . ?
C8 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C19 C14 C15 117.9(4) . . ?
C19 C14 C7 119.5(4) . . ?
C15 C14 C7 122.6(3) . . ?
C14 C15 C16 120.9(5) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C17 C16 C15 120.2(5) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C16 119.3(5) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C19 121.6(5) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C14 C19 C18 120.1(5) . . ?
C14 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
O1 C20 C21 113.5(5) . . ?
O1 C20 H20A 108.9 . . ?
C21 C20 H20A 108.9 . . ?
O1 C20 H20B 108.9 . . ?
C21 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
C20 C21 C22 103.9(4) . . ?
C20 C21 H21A 111.0 . . ?
C22 C21 H21A 111.0 . . ?
C20 C21 H21B 111.0 . . ?
C22 C21 H21B 111.0 . . ?
H21A C21 H21B 109.0 . . ?
C21 C22 C23 102.8(4) . . ?
C21 C22 H22A 111.2 . . ?
C23 C22 H22A 111.2 . . ?
C21 C22 H22B 111.2 . . ?
C23 C22 H22B 111.2 . . ?
H22A C22 H22B 109.1 . . ?
O1 C23 C22 106.3(4) . . ?
O1 C23 H23A 110.5 . . ?
C22 C23 H23A 110.5 . . ?
O1 C23 H23B 110.5 . . ?
C22 C23 H23B 110.5 . . ?
H23A C23 H23B 108.7 . . ?
N3 C24 C39 122.1(3) . . ?
N3 C24 C25 115.9(3) . . ?
C39 C24 C25 121.8(3) . . ?
N4 C25 C24 120.7(3) . . ?
N4 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
N4 C26 C27 110.7(3) . . ?
N4 C26 C33 112.1(3) . . ?
C27 C26 C33 114.6(3) . . ?
N4 C26 H26 106.3 . . ?
C27 C26 H26 106.3 . . ?
C33 C26 H26 106.3 . . ?
C32 C27 C28 118.3(3) . . ?
C32 C27 C26 119.0(3) . . ?
C28 C27 C26 122.6(3) . . ?
C27 C28 C29 120.4(4) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 H28 119.8 . . ?
C30 C29 C28 120.1(4) . . ?
C30 C29 H29 120.0 . . ?
C28 C29 H29 120.0 . . ?
C29 C30 C31 120.0(4) . . ?
C29 C30 H30 120.0 . . ?
C31 C30 H30 120.0 . . ?
C30 C31 C32 119.6(4) . . ?
C30 C31 H31 120.2 . . ?
C32 C31 H31 120.2 . . ?
C27 C32 C31 121.5(4) . . ?
C27 C32 H32 119.2 . . ?
C31 C32 H32 119.2 . . ?
C34 C33 C38 118.2(4) . . ?
C34 C33 C26 119.0(3) . . ?
C38 C33 C26 122.8(3) . . ?
C33 C34 C35 121.1(4) . . ?
C33 C34 H34 119.5 . . ?
C35 C34 H34 119.5 . . ?
C36 C35 C34 120.4(4) . . ?
C36 C35 H35 119.8 . . ?
C34 C35 H35 119.8 . . ?
C37 C36 C35 119.3(4) . . ?
C37 C36 H36 120.3 . . ?
C35 C36 H36 120.3 . . ?
C36 C37 C38 120.8(4) . . ?
C36 C37 H37 119.6 . . ?
C38 C37 H37 119.6 . . ?
C33 C38 C37 120.3(4) . . ?
C33 C38 H38 119.8 . . ?
C37 C38 H38 119.8 . . ?
C24 C39 C40 119.2(3) . . ?
C24 C39 H39 120.4 . . ?
C40 C39 H39 120.4 . . ?
C41 C40 C39 118.9(3) . . ?
C41 C40 H40 120.6 . . ?
C39 C40 H40 120.6 . . ?
C40 C41 C42 119.1(3) . . ?
C40 C41 H41 120.4 . . ?
C42 C41 H41 120.4 . . ?
N3 C42 C41 122.4(3) . . ?
N3 C42 H42 118.8 . . ?
C41 C42 H42 118.8 . . ?
O2 C43 C44 104.1(3) . . ?
O2 C43 H43A 110.9 . . ?
C44 C43 H43A 110.9 . . ?
O2 C43 H43B 110.9 . . ?
C44 C43 H43B 110.9 . . ?
H43A C43 H43B 109.0 . . ?
C45 C44 C43 103.5(4) . . ?
C45 C44 H44A 111.1 . . ?
C43 C44 H44A 111.1 . . ?
C45 C44 H44B 111.1 . . ?
C43 C44 H44B 111.1 . . ?
H44A C44 H44B 109.0 . . ?
C44 C45 C46 103.5(4) . . ?
C44 C45 H45A 111.1 . . ?
C46 C45 H45A 111.1 . . ?
C44 C45 H45B 111.1 . . ?
C46 C45 H45B 111.1 . . ?
H45A C45 H45B 109.0 . . ?
O2 C46 C45 105.7(4) . . ?
O2 C46 H46A 110.6 . . ?
C45 C46 H46A 110.6 . . ?
O2 C46 H46B 110.6 . . ?
C45 C46 H46B 110.6 . . ?
H46A C46 H46B 108.7 . . ?

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
C5 N1 C1 C2 0.1(5) . . . . ?
In1 N1 C1 C2 -179.6(2) . . . . ?
N1 C1 C2 C3 -1.0(5) . . . . ?
C1 C2 C3 C4 1.4(5) . . . . ?
C2 C3 C4 C5 -0.8(5) . . . . ?
C1 N1 C5 C4 0.5(5) . . . . ?
In1 N1 C5 C4 -179.8(2) . . . . ?
C1 N1 C5 C6 -179.1(3) . . . . ?
In1 N1 C5 C6 0.6(3) . . . . ?
C3 C4 C5 N1 -0.1(5) . . . . ?
C3 C4 C5 C6 179.5(3) . . . . ?
C7 N2 C6 C5 176.7(3) . . . . ?
In1 N2 C6 C5 2.0(4) . . . . ?
N1 C5 C6 N2 -1.8(5) . . . . ?
C4 C5 C6 N2 178.6(3) . . . . ?
C6 N2 C7 C8 114.7(3) . . . . ?
In1 N2 C7 C8 -71.0(3) . . . . ?
C6 N2 C7 C14 -13.8(4) . . . . ?
In1 N2 C7 C14 160.5(2) . . . . ?
N2 C7 C8 C13 -37.6(5) . . . . ?
C14 C7 C8 C13 91.6(4) . . . . ?
N2 C7 C8 C9 146.9(3) . . . . ?
C14 C7 C8 C9 -83.9(4) . . . . ?
C13 C8 C9 C10 -1.5(6) . . . . ?
C7 C8 C9 C10 174.2(4) . . . . ?
C8 C9 C10 C11 1.0(7) . . . . ?
C9 C10 C11 C12 0.6(7) . . . . ?
C10 C11 C12 C13 -1.6(7) . . . . ?
C9 C8 C13 C12 0.5(6) . . . . ?
C7 C8 C13 C12 -175.0(3) . . . . ?
C11 C12 C13 C8 1.0(7) . . . . ?
N2 C7 C14 C19 -82.9(4) . . . . ?
C8 C7 C14 C19 149.6(3) . . . . ?
N2 C7 C14 C15 97.1(4) . . . . ?
C8 C7 C14 C15 -30.4(5) . . . . ?
C19 C14 C15 C16 0.2(7) . . . . ?
C7 C14 C15 C16 -179.8(4) . . . . ?
C14 C15 C16 C17 -0.7(8) . . . . ?
C15 C16 C17 C18 1.0(9) . . . . ?
C16 C17 C18 C19 -0.9(8) . . . . ?
C15 C14 C19 C18 -0.1(6) . . . . ?
C7 C14 C19 C18 179.9(4) . . . . ?
C17 C18 C19 C14 0.5(7) . . . . ?
C23 O1 C20 C21 -15.5(9) . . . . ?
In1 O1 C20 C21 156.1(4) . . . . ?
O1 C20 C21 C22 -4.3(9) . . . . ?
C20 C21 C22 C23 21.6(8) . . . . ?
C20 O1 C23 C22 29.2(8) . . . . ?
In1 O1 C23 C22 -142.5(4) . . . . ?
C21 C22 C23 O1 -31.9(8) . . . . ?
C42 N3 C24 C39 0.6(5) . . . . ?
In2 N3 C24 C39 -173.5(2) . . . . ?
C42 N3 C24 C25 176.3(3) . . . . ?
In2 N3 C24 C25 2.1(4) . . . . ?
C26 N4 C25 C24 -176.5(3) . . . . ?
In2 N4 C25 C24 -5.1(4) . . . . ?
N3 C24 C25 N4 2.1(5) . . . . ?
C39 C24 C25 N4 177.7(3) . . . . ?
C25 N4 C26 C27 -101.1(4) . . . . ?
In2 N4 C26 C27 88.1(3) . . . . ?
C25 N4 C26 C33 28.3(4) . . . . ?
In2 N4 C26 C33 -142.6(2) . . . . ?
N4 C26 C27 C32 -139.5(3) . . . . ?
C33 C26 C27 C32 92.5(4) . . . . ?
N4 C26 C27 C28 42.8(4) . . . . ?
C33 C26 C27 C28 -85.2(4) . . . . ?
C32 C27 C28 C29 0.4(6) . . . . ?
C26 C27 C28 C29 178.1(3) . . . . ?
C27 C28 C29 C30 -0.9(6) . . . . ?
C28 C29 C30 C31 0.9(7) . . . . ?
C29 C30 C31 C32 -0.4(8) . . . . ?
C28 C27 C32 C31 0.1(6) . . . . ?
C26 C27 C32 C31 -177.7(4) . . . . ?
C30 C31 C32 C27 -0.1(7) . . . . ?
N4 C26 C33 C34 71.5(4) . . . . ?
C27 C26 C33 C34 -161.3(3) . . . . ?
N4 C26 C33 C38 -108.1(4) . . . . ?
C27 C26 C33 C38 19.2(5) . . . . ?
C38 C33 C34 C35 0.0(5) . . . . ?
C26 C33 C34 C35 -179.5(3) . . . . ?
C33 C34 C35 C36 0.6(6) . . . . ?
C34 C35 C36 C37 -0.6(6) . . . . ?
C35 C36 C37 C38 -0.1(7) . . . . ?
C34 C33 C38 C37 -0.7(6) . . . . ?
C26 C33 C38 C37 178.8(3) . . . . ?
C36 C37 C38 C33 0.8(7) . . . . ?
N3 C24 C39 C40 -0.2(5) . . . . ?
C25 C24 C39 C40 -175.6(3) . . . . ?
C24 C39 C40 C41 0.0(5) . . . . ?
C39 C40 C41 C42 -0.3(5) . . . . ?
C24 N3 C42 C41 -1.0(5) . . . . ?
In2 N3 C42 C41 172.6(2) . . . . ?
C40 C41 C42 N3 0.8(5) . . . . ?
C46 O2 C43 C44 15.9(5) . . . . ?
In2 O2 C43 C44 177.2(3) . . . . ?
O2 C43 C44 C45 -33.7(5) . . . . ?
C43 C44 C45 C46 37.8(6) . . . . ?
C43 O2 C46 C45 7.3(6) . . . . ?
In2 O2 C46 C45 -154.0(3) . . . . ?
C44 C45 C46 O2 -28.5(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1 Cl3 0.93 2.77 3.382(4) 124.6 . yes
C2 H2 Cl4 0.93 2.96 3.887(4) 172.5 2_666 yes
C7 H7 Cl2 0.98 2.95 3.514(4) 117.9 . yes
C23 H23B Cl3 0.97 2.92 3.557(7) 124.2 . yes
C26 H26 Cl5 0.98 2.96 3.548(4) 119.2 . yes
C41 H41 Cl1 0.93 2.94 3.869(4) 174.1 2_666 yes
C42 H42 Cl6 0.93 2.72 3.352(4) 125.6 . yes
C45 H45B Cl3 0.97 2.95 3.863(6) 156.7 . yes
C1 H1 Cl3 0.93 2.77 3.382(4) 124.6 . yes
C2 H2 Cl4 0.93 2.96 3.887(4) 172.5 2_666 yes
C7 H7 Cl2 0.98 2.95 3.514(4) 117.9 . yes
C23 H23B Cl3 0.97 2.92 3.557(7) 124.2 . yes
C26 H26 Cl5 0.98 2.96 3.548(4) 119.2 . yes
C41 H41 Cl1 0.93 2.94 3.869(4) 174.1 2_666 yes
C42 H42 Cl6 0.93 2.72 3.352(4) 125.6 . yes
C45 H45B Cl3 0.97 2.95 3.863(6) 156.7 . yes

_refine_diff_density_max         0.644
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.062



####################################################################### 
# 
# 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 2374056'
loop_
_audit_author_name
_audit_author_address
'Tarun Kanti Panda'
;IIT Hyderabad
India
;
_audit_update_record             
;
2024-07-28 deposited with the CCDC.	2024-11-11 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         ?
_chemical_formula_sum            'C18 H22 Cl2 In N2 O P S'
_chemical_formula_weight         531.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
In In -0.7276 1.3100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'
O O 0.0106 0.0060 '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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 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'

_cell_length_a                   21.0292(11)
_cell_length_b                   7.9555(4)
_cell_length_c                   14.0135(6)
_cell_angle_alpha                90
_cell_angle_beta                 112.329(2)
_cell_angle_gamma                90
_cell_volume                     2168.64(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    19543
_cell_measurement_theta_min      2.979
_cell_measurement_theta_max      27.169

_exptl_crystal_description       plates
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_F_000             1064
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    1.516
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.651
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Bruker (Mo) X-ray Source'
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19543
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.979
_diffrn_reflns_theta_max         27.169
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4746
_reflns_number_gt                4402
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.979
_reflns_Friedel_fraction_max     0.975
_reflns_Friedel_fraction_full    0.989

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

_computing_data_collection       
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP 3.0 & Olex 2.1'
_computing_publication_material  WinGX
_refine_special_details          
;
 Refined as a 2-component 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)+(0.0376P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2000 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4746
_refine_ls_number_parameters     236
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_ref         0.0688
_refine_ls_wR_factor_gt          0.0677
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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 0.58622(4) 0.49724(3) 0.62098(5) 0.03249(10) Uani 1 1 d . . . . .
S1 S 0.49699(6) 0.72701(16) 0.64333(9) 0.0462(3) Uani 1 1 d . . . . .
P1 P 0.44640(5) 0.64260(13) 0.49979(7) 0.0319(2) Uani 1 1 d . . . . .
Cl1 Cl 0.58610(7) 0.29901(17) 0.74799(9) 0.0569(3) Uani 1 1 d . . . . .
Cl2 Cl 0.68520(7) 0.66762(19) 0.68305(12) 0.0670(4) Uani 1 1 d . . . . .
O1 O 0.74862(18) 0.2351(5) 0.5527(3) 0.0607(10) Uani 1 1 d . . . . .
N1 N 0.5017(2) 0.5205(4) 0.4799(3) 0.0338(9) Uani 1 1 d . . . . .
N2 N 0.60526(18) 0.2868(4) 0.5120(3) 0.0341(7) Uani 1 1 d . . . . .
C1 C 0.4884(2) 0.3906(6) 0.4017(3) 0.0449(11) Uani 1 1 d . . . . .
H1A H 0.499448 0.432105 0.344703 0.054 Uiso 1 1 calc R U . . .
H1B H 0.440216 0.359670 0.375324 0.054 Uiso 1 1 calc R U . . .
C2 C 0.5325(2) 0.2387(6) 0.4499(4) 0.0447(10) Uani 1 1 d . . . . .
H2A H 0.513464 0.181060 0.493983 0.054 Uiso 1 1 calc R U . . .
H2B H 0.531593 0.161421 0.395812 0.054 Uiso 1 1 calc R U . . .
C3 C 0.6379(3) 0.3501(7) 0.4422(4) 0.0461(11) Uani 1 1 d . . . . .
H3A H 0.615868 0.454183 0.410587 0.055 Uiso 1 1 calc R U . . .
H3B H 0.631409 0.268824 0.387697 0.055 Uiso 1 1 calc R U . . .
C4 C 0.7141(3) 0.3805(7) 0.5003(5) 0.0577(13) Uani 1 1 d . . . . .
H4A H 0.734444 0.416519 0.452083 0.069 Uiso 1 1 calc R U . . .
H4B H 0.720311 0.470291 0.549898 0.069 Uiso 1 1 calc R U . . .
C5 C 0.7183(3) 0.1772(7) 0.6212(4) 0.0560(13) Uani 1 1 d . . . . .
H5A H 0.722495 0.263437 0.672204 0.067 Uiso 1 1 calc R U . . .
H5B H 0.742703 0.078256 0.657241 0.067 Uiso 1 1 calc R U . . .
C6 C 0.6433(3) 0.1344(6) 0.5645(4) 0.0441(10) Uani 1 1 d . . . . .
H6A H 0.638754 0.047092 0.514049 0.053 Uiso 1 1 calc R U . . .
H6B H 0.624078 0.092649 0.612897 0.053 Uiso 1 1 calc R U . . .
C7 C 0.4199(2) 0.8104(5) 0.4071(3) 0.0339(8) Uani 1 1 d . . . . .
C8 C 0.4443(3) 0.8176(6) 0.3278(4) 0.0424(10) Uani 1 1 d . . . . .
H8 H 0.475605 0.737494 0.324337 0.051 Uiso 1 1 calc R U . . .
C9 C 0.4225(3) 0.9423(7) 0.2543(4) 0.0517(12) Uani 1 1 d . . . . .
H9 H 0.438638 0.944906 0.201094 0.062 Uiso 1 1 calc R U . . .
C10 C 0.3770(3) 1.0628(7) 0.2591(4) 0.0544(13) Uani 1 1 d . . . . .
H10 H 0.362282 1.146714 0.209245 0.065 Uiso 1 1 calc R U . . .
C11 C 0.3534(3) 1.0584(9) 0.3385(5) 0.0567(14) Uani 1 1 d . . . . .
H11 H 0.322677 1.139876 0.341999 0.068 Uiso 1 1 calc R U . . .
C12 C 0.3751(3) 0.9338(7) 0.4132(5) 0.0484(11) Uani 1 1 d . . . . .
H12 H 0.359691 0.933045 0.467209 0.058 Uiso 1 1 calc R U . . .
C13 C 0.3684(3) 0.5301(6) 0.4837(4) 0.0381(10) Uani 1 1 d . . . . .
C14 C 0.3688(3) 0.4190(7) 0.5610(4) 0.0536(13) Uani 1 1 d . . . . .
H14 H 0.408323 0.407008 0.620190 0.064 Uiso 1 1 calc R U . . .
C15 C 0.3106(3) 0.3266(7) 0.5498(5) 0.0632(15) Uani 1 1 d . . . . .
H15 H 0.310871 0.253661 0.601821 0.076 Uiso 1 1 calc R U . . .
C16 C 0.2526(3) 0.3426(6) 0.4620(5) 0.0536(13) Uani 1 1 d . . . . .
H16 H 0.213777 0.279467 0.454651 0.064 Uiso 1 1 calc R U . . .
C17 C 0.2510(3) 0.4503(7) 0.3853(4) 0.0474(11) Uani 1 1 d . . . . .
H17 H 0.211197 0.460767 0.326428 0.057 Uiso 1 1 calc R U . . .
C18 C 0.3094(3) 0.5451(8) 0.3952(5) 0.0423(11) Uani 1 1 d . . . . .
H18 H 0.308624 0.617488 0.342617 0.051 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 2.105(4) . ?
In1 Cl2 2.3559(14) . ?
In1 Cl1 2.3787(13) . ?
In1 N2 2.401(4) . ?
In1 S1 2.7216(13) . ?
In1 P1 3.0121(13) . ?
S1 P1 2.0008(16) . ?
P1 N1 1.619(4) . ?
P1 C7 1.797(4) . ?
P1 C13 1.807(5) . ?
O1 C4 1.414(7) . ?
O1 C5 1.417(7) . ?
N1 C1 1.454(6) . ?
N2 C3 1.479(6) . ?
N2 C6 1.484(6) . ?
N2 C2 1.494(6) . ?
C1 C2 1.517(7) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.517(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.511(8) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C12 1.385(7) . ?
C7 C8 1.391(6) . ?
C8 C9 1.377(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.373(10) . ?
C9 H9 0.9300 . ?
C10 C11 1.381(9) . ?
C10 H10 0.9300 . ?
C11 C12 1.387(9) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C18 1.387(8) . ?
C13 C14 1.394(8) . ?
C14 C15 1.385(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.370(9) . ?
C15 H15 0.9300 . ?
C16 C17 1.365(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.402(8) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?

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 Cl2 127.47(12) . . ?
N1 In1 Cl1 121.36(12) . . ?
Cl2 In1 Cl1 110.93(7) . . ?
N1 In1 N2 75.45(13) . . ?
Cl2 In1 N2 107.38(10) . . ?
Cl1 In1 N2 93.53(9) . . ?
N1 In1 S1 71.11(11) . . ?
Cl2 In1 S1 97.01(5) . . ?
Cl1 In1 S1 99.35(5) . . ?
N2 In1 S1 146.17(9) . . ?
N1 In1 P1 30.89(11) . . ?
Cl2 In1 P1 121.57(5) . . ?
Cl1 In1 P1 113.46(5) . . ?
N2 In1 P1 105.79(9) . . ?
S1 In1 P1 40.45(3) . . ?
P1 S1 In1 77.61(5) . . ?
N1 P1 C7 111.5(2) . . ?
N1 P1 C13 111.1(2) . . ?
C7 P1 C13 105.1(2) . . ?
N1 P1 S1 103.41(17) . . ?
C7 P1 S1 112.19(15) . . ?
C13 P1 S1 113.73(19) . . ?
N1 P1 In1 41.86(16) . . ?
C7 P1 In1 131.35(14) . . ?
C13 P1 In1 121.72(17) . . ?
S1 P1 In1 61.94(4) . . ?
C4 O1 C5 110.1(4) . . ?
C1 N1 P1 127.7(3) . . ?
C1 N1 In1 119.8(3) . . ?
P1 N1 In1 107.2(2) . . ?
C3 N2 C6 108.0(4) . . ?
C3 N2 C2 109.4(4) . . ?
C6 N2 C2 108.6(3) . . ?
C3 N2 In1 114.5(3) . . ?
C6 N2 In1 116.3(3) . . ?
C2 N2 In1 99.7(3) . . ?
N1 C1 C2 108.7(4) . . ?
N1 C1 H1A 110.0 . . ?
C2 C1 H1A 110.0 . . ?
N1 C1 H1B 110.0 . . ?
C2 C1 H1B 110.0 . . ?
H1A C1 H1B 108.3 . . ?
N2 C2 C1 111.9(4) . . ?
N2 C2 H2A 109.2 . . ?
C1 C2 H2A 109.2 . . ?
N2 C2 H2B 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
N2 C3 C4 111.1(4) . . ?
N2 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
N2 C3 H3B 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
O1 C4 C3 112.2(4) . . ?
O1 C4 H4A 109.2 . . ?
C3 C4 H4A 109.2 . . ?
O1 C4 H4B 109.2 . . ?
C3 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
O1 C5 C6 111.4(4) . . ?
O1 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
O1 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
N2 C6 C5 109.6(4) . . ?
N2 C6 H6A 109.8 . . ?
C5 C6 H6A 109.8 . . ?
N2 C6 H6B 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
C12 C7 C8 119.1(4) . . ?
C12 C7 P1 120.8(4) . . ?
C8 C7 P1 120.1(3) . . ?
C9 C8 C7 120.5(5) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C10 C9 C8 120.5(5) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 119.4(5) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C10 C11 C12 120.7(6) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C7 C12 C11 119.7(5) . . ?
C7 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C18 C13 C14 119.3(5) . . ?
C18 C13 P1 122.0(4) . . ?
C14 C13 P1 118.7(4) . . ?
C15 C14 C13 120.3(5) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 119.9(5) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C15 120.8(5) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 120.1(5) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C13 C18 C17 119.5(5) . . ?
C13 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?

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
C7 P1 N1 C1 -77.5(5) . . . . ?
C13 P1 N1 C1 39.4(5) . . . . ?
S1 P1 N1 C1 161.7(4) . . . . ?
In1 P1 N1 C1 153.9(5) . . . . ?
C7 P1 N1 In1 128.6(2) . . . . ?
C13 P1 N1 In1 -114.5(2) . . . . ?
S1 P1 N1 In1 7.9(2) . . . . ?
P1 N1 C1 C2 -138.7(4) . . . . ?
In1 N1 C1 C2 12.3(5) . . . . ?
C3 N2 C2 C1 -67.8(5) . . . . ?
C6 N2 C2 C1 174.6(4) . . . . ?
In1 N2 C2 C1 52.5(4) . . . . ?
N1 C1 C2 N2 -46.8(6) . . . . ?
C6 N2 C3 C4 -55.1(5) . . . . ?
C2 N2 C3 C4 -173.1(4) . . . . ?
In1 N2 C3 C4 76.1(4) . . . . ?
C5 O1 C4 C3 -57.0(6) . . . . ?
N2 C3 C4 O1 56.1(6) . . . . ?
C4 O1 C5 C6 59.7(6) . . . . ?
C3 N2 C6 C5 57.2(5) . . . . ?
C2 N2 C6 C5 175.7(4) . . . . ?
In1 N2 C6 C5 -73.0(5) . . . . ?
O1 C5 C6 N2 -60.8(5) . . . . ?
N1 P1 C7 C12 -177.0(4) . . . . ?
C13 P1 C7 C12 62.6(4) . . . . ?
S1 P1 C7 C12 -61.5(4) . . . . ?
In1 P1 C7 C12 -133.0(3) . . . . ?
N1 P1 C7 C8 3.1(4) . . . . ?
C13 P1 C7 C8 -117.3(4) . . . . ?
S1 P1 C7 C8 118.6(3) . . . . ?
In1 P1 C7 C8 47.1(4) . . . . ?
C12 C7 C8 C9 -2.2(7) . . . . ?
P1 C7 C8 C9 177.7(4) . . . . ?
C7 C8 C9 C10 0.9(8) . . . . ?
C8 C9 C10 C11 0.2(9) . . . . ?
C9 C10 C11 C12 0.0(10) . . . . ?
C8 C7 C12 C11 2.3(8) . . . . ?
P1 C7 C12 C11 -177.6(5) . . . . ?
C10 C11 C12 C7 -1.3(10) . . . . ?
N1 P1 C13 C18 -101.9(5) . . . . ?
C7 P1 C13 C18 18.8(5) . . . . ?
S1 P1 C13 C18 141.9(4) . . . . ?
In1 P1 C13 C18 -147.5(4) . . . . ?
N1 P1 C13 C14 75.0(5) . . . . ?
C7 P1 C13 C14 -164.3(4) . . . . ?
S1 P1 C13 C14 -41.2(5) . . . . ?
In1 P1 C13 C14 29.4(5) . . . . ?
C18 C13 C14 C15 -0.9(8) . . . . ?
P1 C13 C14 C15 -177.9(4) . . . . ?
C13 C14 C15 C16 0.8(9) . . . . ?
C14 C15 C16 C17 -0.6(9) . . . . ?
C15 C16 C17 C18 0.6(9) . . . . ?
C14 C13 C18 C17 0.9(8) . . . . ?
P1 C13 C18 C17 177.8(4) . . . . ?
C16 C17 C18 C13 -0.7(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C5 H5A Cl1 0.97 3.43 3.947(6) 115.7 . yes
C5 H5A Cl1 0.97 3.43 3.947(6) 115.7 . yes

_refine_diff_density_max         0.819
_refine_diff_density_min         -0.723
_refine_diff_density_rms         0.066



####################################################################### 
# 
# 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 2374057'
loop_
_audit_author_name
_audit_author_address
'Tarun Kanti Panda'
;IIT Hyderabad
India
;
_audit_update_record             
;
2024-07-28 deposited with the CCDC.	2024-11-11 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         ?
_chemical_formula_sum            'C22 H32 Cl In N6 O2'
_chemical_formula_weight         562.80

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
O O 0.0106 0.0060 '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'
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'

_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                   18.309(2)
_cell_length_b                   9.8212(9)
_cell_length_c                   15.5256(14)
_cell_angle_alpha                90
_cell_angle_beta                 115.026(3)
_cell_angle_gamma                90
_cell_volume                     2529.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    76971
_cell_measurement_theta_min      2.410
_cell_measurement_theta_max      27.163

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    1.069
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.790
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Bruker (Mo) X-ray Source'
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            76971
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_av_R_equivalents  0.0749
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.410
_diffrn_reflns_theta_max         27.163
_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             5619
_reflns_number_gt                4228
_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       
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP 3.0 & Olex 2.1'
_computing_publication_material  WinGX
_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)+(0.0263P)²+0.9528P] 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         5619
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.0676
_refine_ls_wR_factor_gt          0.0611
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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 0.18418(2) 0.73308(2) 0.30179(2) 0.04446(7) Uani 1 1 d . . . . .
Cl1 Cl 0.10068(4) 0.82860(8) 0.37702(5) 0.0625(2) Uani 1 1 d . . . . .
O1 O 0.10733(17) 1.1374(3) 0.1484(2) 0.1008(8) Uani 1 1 d . . . . .
O2 O 0.56013(15) 0.3536(3) 0.35967(18) 0.0885(7) Uani 1 1 d . . . . .
N1 N 0.21833(14) 0.5452(2) 0.38597(16) 0.0552(6) Uani 1 1 d . . . . .
N2 N 0.09812(13) 0.5792(2) 0.21351(16) 0.0570(6) Uani 1 1 d . . . . .
N3 N 0.10209(14) 0.8443(2) 0.14589(16) 0.0565(6) Uani 1 1 d . . . . .
N4 N 0.28019(12) 0.8730(2) 0.37283(15) 0.0480(5) Uani 1 1 d . . . . .
N5 N 0.27908(13) 0.6894(2) 0.24126(16) 0.0532(6) Uani 1 1 d . . . . .
N6 N 0.39908(15) 0.4566(2) 0.28523(19) 0.0629(7) Uani 1 1 d . . . . .
C1 C 0.2750(2) 0.4989(3) 0.4689(2) 0.0692(9) Uani 1 1 d . . . . .
H1 H 0.314595 0.551893 0.514566 0.083 Uiso 1 1 calc R U . . .
C2 C 0.2653(2) 0.3598(4) 0.4756(3) 0.0837(11) Uani 1 1 d . . . . .
H2 H 0.296637 0.303873 0.526098 0.100 Uiso 1 1 calc R U . . .
C3 C 0.2014(2) 0.3201(3) 0.3948(3) 0.0824(10) Uani 1 1 d . . . . .
H3 H 0.180791 0.232365 0.379675 0.099 Uiso 1 1 calc R U . . .
C4 C 0.17282(18) 0.4360(3) 0.3393(2) 0.0597(7) Uani 1 1 d . . . . .
C5 C 0.10988(18) 0.4584(3) 0.2480(2) 0.0629(8) Uani 1 1 d . . . . .
H5 H 0.077604 0.386613 0.213513 0.075 Uiso 1 1 calc R U . . .
C6 C 0.03543(19) 0.6169(4) 0.1224(2) 0.0744(9) Uani 1 1 d . . . . .
H6A H -0.011318 0.650562 0.129933 0.089 Uiso 1 1 calc R U . . .
H6B H 0.019242 0.538548 0.080423 0.089 Uiso 1 1 calc R U . . .
C7 C 0.0688(2) 0.7266(4) 0.0810(2) 0.0832(11) Uani 1 1 d . . . . .
H7A H 0.110906 0.687919 0.066314 0.100 Uiso 1 1 calc R U . . .
H7B H 0.026215 0.758536 0.021956 0.100 Uiso 1 1 calc R U . . .
C8 C 0.03701(18) 0.9307(4) 0.1466(2) 0.0706(9) Uani 1 1 d . . . . .
H8A H 0.009931 0.883628 0.179810 0.085 Uiso 1 1 calc R U . . .
H8B H -0.002140 0.946125 0.081746 0.085 Uiso 1 1 calc R U . . .
C9 C 0.0667(2) 1.0627(4) 0.1929(3) 0.0893(12) Uani 1 1 d . . . . .
H9A H 0.021503 1.115911 0.191318 0.107 Uiso 1 1 calc R U . . .
H9B H 0.103113 1.047542 0.258961 0.107 Uiso 1 1 calc R U . . .
C10 C 0.1500(2) 0.9278(4) 0.1054(2) 0.0823(11) Uani 1 1 d . . . . .
H10A H 0.198013 0.877909 0.112827 0.099 Uiso 1 1 calc R U . . .
H10B H 0.117743 0.942066 0.037933 0.099 Uiso 1 1 calc R U . . .
C11 C 0.1738(2) 1.0634(4) 0.1544(3) 0.0979(13) Uani 1 1 d . . . . .
H11A H 0.209784 1.048975 0.220740 0.117 Uiso 1 1 calc R U . . .
H11B H 0.202814 1.115181 0.125607 0.117 Uiso 1 1 calc R U . . .
C12 C 0.29667(18) 0.9749(3) 0.43663(19) 0.0557(7) Uani 1 1 d . . . . .
H12 H 0.262371 1.004096 0.463149 0.067 Uiso 1 1 calc R U . . .
C13 C 0.37112(19) 1.0295(3) 0.4568(2) 0.0658(8) Uani 1 1 d . . . . .
H13 H 0.395918 1.100431 0.498720 0.079 Uiso 1 1 calc R U . . .
C14 C 0.40219(18) 0.9584(3) 0.4029(2) 0.0636(8) Uani 1 1 d . . . . .
H14 H 0.451973 0.972390 0.401627 0.076 Uiso 1 1 calc R U . . .
C15 C 0.34490(15) 0.8625(3) 0.35105(19) 0.0499(6) Uani 1 1 d . . . . .
C16 C 0.34175(17) 0.7636(3) 0.2827(2) 0.0559(7) Uani 1 1 d . . . . .
H16 H 0.385629 0.752845 0.267924 0.067 Uiso 1 1 calc R U . . .
C17 C 0.28044(19) 0.5867(3) 0.1738(2) 0.0741(9) Uani 1 1 d . . . . .
H17A H 0.312621 0.620260 0.142192 0.089 Uiso 1 1 calc R U . . .
H17B H 0.225976 0.572675 0.125682 0.089 Uiso 1 1 calc R U . . .
C18 C 0.3143(2) 0.4524(3) 0.2202(3) 0.0803(10) Uani 1 1 d . . . . .
H18A H 0.283834 0.421764 0.254748 0.096 Uiso 1 1 calc R U . . .
H18B H 0.306747 0.385844 0.171028 0.096 Uiso 1 1 calc R U . . .
C19 C 0.4230(3) 0.3331(4) 0.3423(3) 0.0915(12) Uani 1 1 d . . . . .
H19A H 0.412261 0.254734 0.300645 0.110 Uiso 1 1 calc R U . . .
H19B H 0.391242 0.323741 0.378528 0.110 Uiso 1 1 calc R U . . .
C20 C 0.5109(3) 0.3360(4) 0.4091(3) 0.1047(14) Uani 1 1 d . . . . .
H20A H 0.520758 0.409980 0.454028 0.126 Uiso 1 1 calc R U . . .
H20B H 0.525281 0.251475 0.444634 0.126 Uiso 1 1 calc R U . . .
C21 C 0.5377(2) 0.4765(4) 0.3081(3) 0.0768(10) Uani 1 1 d . . . . .
H21A H 0.571946 0.491795 0.275456 0.092 Uiso 1 1 calc R U . . .
H21B H 0.545577 0.551550 0.351725 0.092 Uiso 1 1 calc R U . . .
C22 C 0.45135(18) 0.4730(3) 0.2369(2) 0.0664(8) Uani 1 1 d . . . . .
H22A H 0.438064 0.556956 0.200511 0.080 Uiso 1 1 calc R U . . .
H22B H 0.443146 0.397980 0.193097 0.080 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 N4 2.134(2) . ?
In1 N1 2.194(2) . ?
In1 N2 2.195(2) . ?
In1 N5 2.338(2) . ?
In1 Cl1 2.4684(7) . ?
In1 N3 2.497(2) . ?
O1 C11 1.387(4) . ?
O1 C9 1.416(4) . ?
O2 C21 1.410(4) . ?
O2 C20 1.420(4) . ?
N1 C1 1.345(4) . ?
N1 C4 1.363(4) . ?
N2 C5 1.282(4) . ?
N2 C6 1.443(4) . ?
N3 C8 1.467(3) . ?
N3 C7 1.484(4) . ?
N3 C10 1.517(4) . ?
N4 C12 1.350(3) . ?
N4 C15 1.367(3) . ?
N5 C16 1.280(3) . ?
N5 C17 1.462(3) . ?
N6 C18 1.451(4) . ?
N6 C22 1.454(4) . ?
N6 C19 1.456(4) . ?
C1 C2 1.387(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.361(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.390(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.416(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.509(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.470(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.504(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.372(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.386(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.422(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.505(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.501(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.498(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?

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
N4 In1 N1 105.60(8) . . ?
N4 In1 N2 169.36(8) . . ?
N1 In1 N2 75.00(9) . . ?
N4 In1 N5 74.71(8) . . ?
N1 In1 N5 90.69(8) . . ?
N2 In1 N5 94.69(8) . . ?
N4 In1 Cl1 92.89(6) . . ?
N1 In1 Cl1 96.62(6) . . ?
N2 In1 Cl1 97.61(7) . . ?
N5 In1 Cl1 166.97(6) . . ?
N4 In1 N3 104.22(8) . . ?
N1 In1 N3 148.06(9) . . ?
N2 In1 N3 73.57(9) . . ?
N5 In1 N3 86.31(8) . . ?
Cl1 In1 N3 93.04(6) . . ?
C11 O1 C9 108.9(3) . . ?
C21 O2 C20 108.2(3) . . ?
C1 N1 C4 107.1(3) . . ?
C1 N1 In1 139.8(2) . . ?
C4 N1 In1 112.87(19) . . ?
C5 N2 C6 124.8(3) . . ?
C5 N2 In1 115.3(2) . . ?
C6 N2 In1 119.9(2) . . ?
C8 N3 C7 110.7(3) . . ?
C8 N3 C10 107.7(2) . . ?
C7 N3 C10 106.4(3) . . ?
C8 N3 In1 113.78(17) . . ?
C7 N3 In1 102.91(17) . . ?
C10 N3 In1 114.96(17) . . ?
C12 N4 C15 106.8(2) . . ?
C12 N4 In1 137.43(19) . . ?
C15 N4 In1 115.75(17) . . ?
C16 N5 C17 118.0(2) . . ?
C16 N5 In1 110.73(18) . . ?
C17 N5 In1 130.95(19) . . ?
C18 N6 C22 112.9(3) . . ?
C18 N6 C19 110.9(3) . . ?
C22 N6 C19 108.2(2) . . ?
N1 C1 C2 109.5(3) . . ?
N1 C1 H1 125.3 . . ?
C2 C1 H1 125.3 . . ?
C3 C2 C1 107.5(3) . . ?
C3 C2 H2 126.3 . . ?
C1 C2 H2 126.3 . . ?
C2 C3 C4 106.8(3) . . ?
C2 C3 H3 126.6 . . ?
C4 C3 H3 126.6 . . ?
N1 C4 C3 109.2(3) . . ?
N1 C4 C5 117.8(3) . . ?
C3 C4 C5 133.0(3) . . ?
N2 C5 C4 118.9(3) . . ?
N2 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
N2 C6 C7 107.7(3) . . ?
N2 C6 H6A 110.2 . . ?
C7 C6 H6A 110.2 . . ?
N2 C6 H6B 110.2 . . ?
C7 C6 H6B 110.2 . . ?
H6A C6 H6B 108.5 . . ?
N3 C7 C6 113.0(3) . . ?
N3 C7 H7A 109.0 . . ?
C6 C7 H7A 109.0 . . ?
N3 C7 H7B 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
N3 C8 C9 112.4(3) . . ?
N3 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
N3 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
O1 C9 C8 112.4(3) . . ?
O1 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
O1 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 N3 111.3(3) . . ?
C11 C10 H10A 109.4 . . ?
N3 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
N3 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
O1 C11 C10 111.8(3) . . ?
O1 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
O1 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
N4 C12 C13 110.5(3) . . ?
N4 C12 H12 124.8 . . ?
C13 C12 H12 124.8 . . ?
C12 C13 C14 106.7(3) . . ?
C12 C13 H13 126.6 . . ?
C14 C13 H13 126.6 . . ?
C13 C14 C15 106.9(3) . . ?
C13 C14 H14 126.6 . . ?
C15 C14 H14 126.6 . . ?
N4 C15 C14 109.1(2) . . ?
N4 C15 C16 118.1(2) . . ?
C14 C15 C16 132.8(3) . . ?
N5 C16 C15 120.6(2) . . ?
N5 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
N5 C17 C18 112.9(3) . . ?
N5 C17 H17A 109.0 . . ?
C18 C17 H17A 109.0 . . ?
N5 C17 H17B 109.0 . . ?
C18 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
N6 C18 C17 114.3(3) . . ?
N6 C18 H18A 108.7 . . ?
C17 C18 H18A 108.7 . . ?
N6 C18 H18B 108.7 . . ?
C17 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
N6 C19 C20 111.3(3) . . ?
N6 C19 H19A 109.4 . . ?
C20 C19 H19A 109.4 . . ?
N6 C19 H19B 109.4 . . ?
C20 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
O2 C20 C19 111.7(3) . . ?
O2 C20 H20A 109.3 . . ?
C19 C20 H20A 109.3 . . ?
O2 C20 H20B 109.3 . . ?
C19 C20 H20B 109.3 . . ?
H20A C20 H20B 107.9 . . ?
O2 C21 C22 111.3(3) . . ?
O2 C21 H21A 109.4 . . ?
C22 C21 H21A 109.4 . . ?
O2 C21 H21B 109.4 . . ?
C22 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
N6 C22 C21 109.9(3) . . ?
N6 C22 H22A 109.7 . . ?
C21 C22 H22A 109.7 . . ?
N6 C22 H22B 109.7 . . ?
C21 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?

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
C4 N1 C1 C2 -0.5(3) . . . . ?
In1 N1 C1 C2 -174.5(2) . . . . ?
N1 C1 C2 C3 0.3(4) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C1 N1 C4 C3 0.6(3) . . . . ?
In1 N1 C4 C3 176.4(2) . . . . ?
C1 N1 C4 C5 -178.2(3) . . . . ?
In1 N1 C4 C5 -2.5(3) . . . . ?
C2 C3 C4 N1 -0.5(4) . . . . ?
C2 C3 C4 C5 178.1(3) . . . . ?
C6 N2 C5 C4 -178.8(3) . . . . ?
In1 N2 C5 C4 3.1(4) . . . . ?
N1 C4 C5 N2 -0.4(4) . . . . ?
C3 C4 C5 N2 -178.9(3) . . . . ?
C5 N2 C6 C7 -144.7(3) . . . . ?
In1 N2 C6 C7 33.3(3) . . . . ?
C8 N3 C7 C6 -76.2(3) . . . . ?
C10 N3 C7 C6 167.0(3) . . . . ?
In1 N3 C7 C6 45.7(3) . . . . ?
N2 C6 C7 N3 -54.2(4) . . . . ?
C7 N3 C8 C9 -167.5(3) . . . . ?
C10 N3 C8 C9 -51.5(3) . . . . ?
In1 N3 C8 C9 77.2(3) . . . . ?
C11 O1 C9 C8 -61.3(4) . . . . ?
N3 C8 C9 O1 58.6(4) . . . . ?
C8 N3 C10 C11 50.6(3) . . . . ?
C7 N3 C10 C11 169.3(3) . . . . ?
In1 N3 C10 C11 -77.5(3) . . . . ?
C9 O1 C11 C10 60.5(4) . . . . ?
N3 C10 C11 O1 -57.2(4) . . . . ?
C15 N4 C12 C13 -0.5(3) . . . . ?
In1 N4 C12 C13 179.6(2) . . . . ?
N4 C12 C13 C14 0.2(3) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C12 N4 C15 C14 0.6(3) . . . . ?
In1 N4 C15 C14 -179.51(18) . . . . ?
C12 N4 C15 C16 -178.4(2) . . . . ?
In1 N4 C15 C16 1.5(3) . . . . ?
C13 C14 C15 N4 -0.4(3) . . . . ?
C13 C14 C15 C16 178.3(3) . . . . ?
C17 N5 C16 C15 -178.2(3) . . . . ?
In1 N5 C16 C15 -3.6(3) . . . . ?
N4 C15 C16 N5 1.7(4) . . . . ?
C14 C15 C16 N5 -177.0(3) . . . . ?
C16 N5 C17 C18 88.3(4) . . . . ?
In1 N5 C17 C18 -84.9(3) . . . . ?
C22 N6 C18 C17 -70.8(3) . . . . ?
C19 N6 C18 C17 167.6(3) . . . . ?
N5 C17 C18 N6 -66.1(4) . . . . ?
C18 N6 C19 C20 179.4(3) . . . . ?
C22 N6 C19 C20 55.1(4) . . . . ?
C21 O2 C20 C19 58.5(4) . . . . ?
N6 C19 C20 O2 -57.3(4) . . . . ?
C20 O2 C21 C22 -60.9(4) . . . . ?
C18 N6 C22 C21 -180.0(3) . . . . ?
C19 N6 C22 C21 -56.8(4) . . . . ?
O2 C21 C22 N6 61.7(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C7 H7A Cl1 0.97 2.87 3.497(3) 123.3 4_575 yes
C8 H8A Cl1 0.97 2.85 3.410(3) 117.7 . yes
C9 H9A Cl1 0.97 2.91 3.817(4) 155.6 2 yes
C9 H9B Cl1 0.97 2.84 3.513(4) 127.4 . yes
C7 H7A Cl1 0.97 2.87 3.497(3) 123.3 4_575 yes
C8 H8A Cl1 0.97 2.85 3.410(3) 117.7 . yes
C9 H9A Cl1 0.97 2.91 3.817(4) 155.6 2 yes
C9 H9B Cl1 0.97 2.84 3.513(4) 127.4 . yes

_refine_diff_density_max         0.444
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.056



