# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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. 
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#######################################################################

data_mo_VA287_0m
_database_code_depnum_ccdc_archive 'CCDC 2497610'
loop_
_audit_author_name
_audit_author_address
'B. Sridhar'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2025-10-24 deposited with the CCDC.	2026-01-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H11 I N2 O2'
_chemical_formula_sum            'C11 H11 I N2 O2'
_chemical_formula_weight         330.12

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'
I I -0.4742 1.8119 '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                   19.0900(17)
_cell_length_b                   9.6073(8)
_cell_length_c                   20.2257(18)
_cell_angle_alpha                90
_cell_angle_beta                 95.037(3)
_cell_angle_gamma                90
_cell_volume                     3695.1(6)
_cell_formula_units_Z            12
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9182
_cell_measurement_theta_min      2.203
_cell_measurement_theta_max      28.204

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.780
_exptl_crystal_F_000             1920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    2.587
_shelx_estimated_absorpt_T_min   0.600
_shelx_estimated_absorpt_T_max   0.682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5642
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec I\mS 3.0'
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON III C14'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 7.391
_diffrn_reflns_number            42332
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.544
_diffrn_reflns_theta_max         28.265
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             8926
_reflns_number_gt                7385
_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       'APEX5 (Bruker, 2023)'
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_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)+(0.0389P)²+0.9082P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8926
_refine_ls_number_parameters     515
_refine_ls_number_restraints     123
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0267
_refine_ls_wR_factor_ref         0.0766
_refine_ls_wR_factor_gt          0.0710
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.005
_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
C1A C 0.69292(12) 0.3338(2) 0.63541(12) 0.0578(5) Uani 1 1 d . . . . .
H1A H 0.727375 0.311853 0.607339 0.069 Uiso 1 1 calc R U . . .
C2A C 0.69160(11) 0.2889(2) 0.70015(11) 0.0501(4) Uani 1 1 d . . . . .
C3A C 0.63102(10) 0.34722(18) 0.72252(10) 0.0438(4) Uani 1 1 d . . . . .
C4A C 0.60177(10) 0.34395(18) 0.78780(10) 0.0448(4) Uani 1 1 d . . . . .
C5A C 0.64578(12) 0.3465(2) 0.84608(11) 0.0553(5) Uani 1 1 d . . . . .
H5A H 0.694286 0.342499 0.844586 0.066 Uiso 1 1 calc R U . . .
C6A C 0.61716(14) 0.3550(3) 0.90652(11) 0.0611(5) Uani 1 1 d . . . . .
H6A H 0.646871 0.355712 0.945507 0.073 Uiso 1 1 calc R U . . .
C7A C 0.54545(13) 0.3623(2) 0.91000(11) 0.0577(5) Uani 1 1 d . . . . .
H7A H 0.526881 0.370961 0.950799 0.069 Uiso 1 1 calc R U . . .
C8A C 0.50167(11) 0.3566(2) 0.85208(11) 0.0515(4) Uani 1 1 d . . . . .
C9A C 0.52967(11) 0.3464(2) 0.79096(10) 0.0482(4) Uani 1 1 d . . . . .
H9A H 0.499816 0.341284 0.752148 0.058 Uiso 1 1 calc R U . . .
C10A C 0.39623(14) 0.3726(3) 0.90818(13) 0.0728(7) Uani 1 1 d . . . . .
H10C H 0.346468 0.352925 0.899151 0.087 Uiso 1 1 calc R U . . .
H10D H 0.416028 0.302323 0.938807 0.087 Uiso 1 1 calc R U . . .
C11A C 0.3641(2) 0.6062(4) 0.90403(17) 0.1034(11) Uani 1 1 d . . . . .
H11D H 0.372464 0.605036 0.857910 0.155 Uiso 1 1 calc R U . . .
H11E H 0.377585 0.695084 0.922794 0.155 Uiso 1 1 calc R U . . .
H11F H 0.315103 0.590424 0.908393 0.155 Uiso 1 1 calc R U . . .
N1A N 0.63683(10) 0.4135(2) 0.61967(9) 0.0555(4) Uani 1 1 d . . . . .
H1NA H 0.626(2) 0.457(5) 0.580(2) 0.146(16) Uiso 1 1 d . . . . .
N2A N 0.59884(9) 0.42250(17) 0.67288(8) 0.0488(4) Uani 1 1 d . . . . .
O1A O 0.42912(9) 0.3629(2) 0.84798(8) 0.0716(5) Uani 1 1 d . . . . .
O2A O 0.40411(9) 0.50085(19) 0.93775(8) 0.0681(4) Uani 1 1 d . . . . .
I1A I 0.7576(3) 0.1435(5) 0.74673(13) 0.0797(5) Uani 0.568(15) 1 d . U P A 1
I1D I 0.77194(16) 0.1670(4) 0.74652(17) 0.0670(4) Uani 0.432(15) 1 d . U P A 2
C1B C 0.42399(11) 0.6069(2) 0.70439(10) 0.0566(5) Uani 1 1 d . . . . .
H1B H 0.425628 0.571851 0.747355 0.068 Uiso 1 1 calc R U . . .
C2B C 0.37261(10) 0.6932(2) 0.67489(10) 0.0504(4) Uani 1 1 d . . . . .
C3B C 0.39116(9) 0.7192(2) 0.61110(9) 0.0431(4) Uani 1 1 d . . . . .
C4B C 0.35831(9) 0.8047(2) 0.55698(9) 0.0429(4) Uani 1 1 d . . . . .
C5B C 0.28568(10) 0.8039(2) 0.54210(10) 0.0509(4) Uani 1 1 d . . . . .
H5B H 0.257321 0.747299 0.565814 0.061 Uiso 1 1 calc R U . . .
C6B C 0.25627(11) 0.8880(3) 0.49183(12) 0.0593(5) Uani 1 1 d . . . . .
H6B H 0.207672 0.889593 0.482756 0.071 Uiso 1 1 calc R U . . .
C7B C 0.29746(11) 0.9698(3) 0.45473(11) 0.0586(5) Uani 1 1 d . . . . .
H7B H 0.276783 1.025265 0.420745 0.070 Uiso 1 1 calc R U . . .
C8B C 0.36974(10) 0.9687(2) 0.46842(10) 0.0509(4) Uani 1 1 d D . . . .
C9B C 0.40013(10) 0.8880(2) 0.52011(9) 0.0465(4) Uani 1 1 d . . . . .
H9B H 0.448610 0.889558 0.530165 0.056 Uiso 1 1 calc R U . . .
N1B N 0.47081(9) 0.5824(2) 0.66076(9) 0.0528(4) Uani 1 1 d . . . . .
H1NB H 0.509(2) 0.531(4) 0.6686(19) 0.127(13) Uiso 1 1 d . . . . .
N2B N 0.45164(8) 0.65019(17) 0.60387(8) 0.0456(3) Uani 1 1 d . . . . .
C10B C 0.3924(5) 1.1355(12) 0.3845(5) 0.0768(18) Uani 0.678(5) 1 d D U P B 1
H10A H 0.355233 1.194572 0.398488 0.092 Uiso 0.678(5) 1 calc R U P B 1
H10B H 0.430441 1.195922 0.373545 0.092 Uiso 0.678(5) 1 calc R U P B 1
C11B C 0.4234(4) 1.0139(8) 0.2901(3) 0.1194(18) Uani 0.678(5) 1 d D U P B 1
H11J H 0.403374 0.954037 0.255442 0.179 Uiso 0.678(5) 1 calc R U P B 1
H11K H 0.456507 0.962244 0.318979 0.179 Uiso 0.678(5) 1 calc R U P B 1
H11L H 0.446901 1.090308 0.271006 0.179 Uiso 0.678(5) 1 calc R U P B 1
O1B O 0.4172(5) 1.0517(10) 0.4386(4) 0.0653(16) Uani 0.678(5) 1 d D U P B 1
O2B O 0.36736(18) 1.0673(4) 0.32832(15) 0.0906(10) Uani 0.678(5) 1 d D U P B 1
I1B I 0.28652(9) 0.7614(3) 0.72222(8) 0.0692(3) Uani 0.678(5) 1 d . U P B 1
C10E C 0.3809(10) 1.120(3) 0.3782(11) 0.075(2) Uani 0.322(5) 1 d D U P B 2
H10G H 0.343869 1.073058 0.350632 0.090 Uiso 0.322(5) 1 calc R U P B 2
H10H H 0.360998 1.199237 0.399414 0.090 Uiso 0.322(5) 1 calc R U P B 2
C11E C 0.4596(7) 1.0613(16) 0.3016(7) 0.111(3) Uani 0.322(5) 1 d D U P B 2
H11A H 0.425724 1.044294 0.264600 0.166 Uiso 0.322(5) 1 calc R U P B 2
H11B H 0.467975 0.976853 0.326440 0.166 Uiso 0.322(5) 1 calc R U P B 2
H11C H 0.502856 1.092791 0.285749 0.166 Uiso 0.322(5) 1 calc R U P B 2
O1E O 0.4137(11) 1.026(2) 0.4265(8) 0.062(3) Uani 0.322(5) 1 d D U P B 2
O2E O 0.4348(4) 1.1600(8) 0.3412(4) 0.1035(19) Uani 0.322(5) 1 d D U P B 2
I1E I 0.2937(2) 0.7841(5) 0.7224(2) 0.0736(8) Uani 0.322(5) 1 d . U P B 2
C1C C 0.54096(11) 0.7305(2) 0.44040(11) 0.0523(5) Uani 1 1 d . . . . .
H1C H 0.502764 0.782479 0.422535 0.063 Uiso 1 1 calc R U . . .
C2C C 0.60595(11) 0.7241(2) 0.41577(9) 0.0479(4) Uani 1 1 d . . . . .
C3C C 0.64658(10) 0.6352(2) 0.45806(10) 0.0458(4) Uani 1 1 d . . . . .
C4C C 0.72021(10) 0.5883(2) 0.45824(11) 0.0485(4) Uani 1 1 d . . . . .
C5C C 0.74965(12) 0.5616(2) 0.39906(12) 0.0577(5) Uani 1 1 d . . . . .
H5C H 0.723082 0.574003 0.358711 0.069 Uiso 1 1 calc R U . . .
C6C C 0.81833(13) 0.5166(3) 0.40033(13) 0.0669(6) Uani 1 1 d . . . . .
H6C H 0.837982 0.500469 0.360548 0.080 Uiso 1 1 calc R U . . .
C7C C 0.85826(12) 0.4951(2) 0.45931(14) 0.0647(6) Uani 1 1 d . . . . .
H7C H 0.904412 0.464053 0.459473 0.078 Uiso 1 1 calc R U . . .
C8C C 0.82920(11) 0.5201(2) 0.51844(12) 0.0578(5) Uani 1 1 d . . . . .
C9C C 0.76053(11) 0.5681(2) 0.51783(11) 0.0523(5) Uani 1 1 d . . . . .
H9C H 0.741479 0.586769 0.557657 0.063 Uiso 1 1 calc R U . . .
C10C C 0.93768(13) 0.4856(3) 0.58529(18) 0.0868(9) Uani 1 1 d . . . . .
H10E H 0.957402 0.556520 0.558253 0.104 Uiso 1 1 calc R U . . .
H10F H 0.956128 0.500745 0.630956 0.104 Uiso 1 1 calc R U . . .
C11C C 0.9433(3) 0.2491(4) 0.6104(2) 0.1310(16) Uani 1 1 d . . . . .
H11G H 0.893567 0.246616 0.614038 0.196 Uiso 1 1 calc R U . . .
H11H H 0.967410 0.267816 0.653113 0.196 Uiso 1 1 calc R U . . .
H11I H 0.958488 0.160930 0.594412 0.196 Uiso 1 1 calc R U . . .
N1C N 0.54202(9) 0.65018(19) 0.49393(9) 0.0519(4) Uani 1 1 d D . . . .
H1NC H 0.5107(19) 0.641(4) 0.5243(17) 0.144(16) Uiso 1 1 d D . . . .
N2C N 0.60649(8) 0.59196(18) 0.50574(8) 0.0486(4) Uani 1 1 d . . . . .
O1C O 0.86345(8) 0.5007(2) 0.58060(10) 0.0751(5) Uani 1 1 d . . . . .
O2C O 0.95906(11) 0.3561(2) 0.56501(13) 0.0943(7) Uani 1 1 d . . . . .
I1C I 0.63841(15) 0.8482(3) 0.33890(12) 0.0634(3) Uani 0.575(17) 1 d . U P C 1
I1F I 0.6317(2) 0.8285(6) 0.33394(17) 0.0677(6) Uani 0.425(17) 1 d . U P C 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1A N1A 1.332(3) . ?
C1A C2A 1.381(3) . ?
C1A H1A 0.9300 . ?
C2A C3A 1.396(3) . ?
C2A I1A 2.055(3) . ?
C2A I1D 2.086(3) . ?
C3A N2A 1.342(3) . ?
C3A C4A 1.478(3) . ?
C4A C9A 1.384(3) . ?
C4A C5A 1.386(3) . ?
C5A C6A 1.384(3) . ?
C5A H5A 0.9300 . ?
C6A C7A 1.379(4) . ?
C6A H6A 0.9300 . ?
C7A C8A 1.379(3) . ?
C7A H7A 0.9300 . ?
C8A O1A 1.381(3) . ?
C8A C9A 1.393(3) . ?
C9A H9A 0.9300 . ?
C10A O2A 1.372(3) . ?
C10A O1A 1.421(3) . ?
C10A H10C 0.9700 . ?
C10A H10D 0.9700 . ?
C11A O2A 1.407(4) . ?
C11A H11D 0.9600 . ?
C11A H11E 0.9600 . ?
C11A H11F 0.9600 . ?
N1A N2A 1.352(2) . ?
N1A H1NA 0.92(4) . ?
C1B N1B 1.331(3) . ?
C1B C2B 1.379(3) . ?
C1B H1B 0.9300 . ?
C2B C3B 1.390(3) . ?
C2B I1E 2.053(4) . ?
C2B I1B 2.079(3) . ?
C3B N2B 1.351(2) . ?
C3B C4B 1.465(3) . ?
C4B C9B 1.392(3) . ?
C4B C5B 1.393(3) . ?
C5B C6B 1.379(3) . ?
C5B H5B 0.9300 . ?
C6B C7B 1.379(3) . ?
C6B H6B 0.9300 . ?
C7B C8B 1.383(3) . ?
C7B H7B 0.9300 . ?
C8B O1E 1.363(15) . ?
C8B O1B 1.384(7) . ?
C8B C9B 1.387(3) . ?
C9B H9B 0.9300 . ?
N1B N2B 1.345(2) . ?
N1B H1NB 0.89(4) . ?
C10B O2B 1.362(10) . ?
C10B O1B 1.407(8) . ?
C10B H10A 0.9700 . ?
C10B H10B 0.9700 . ?
C11B O2B 1.466(7) . ?
C11B H11J 0.9600 . ?
C11B H11K 0.9600 . ?
C11B H11L 0.9600 . ?
C10E O2E 1.381(16) . ?
C10E O1E 1.429(16) . ?
C10E H10G 0.9700 . ?
C10E H10H 0.9700 . ?
C11E O2E 1.353(13) . ?
C11E H11A 0.9600 . ?
C11E H11B 0.9600 . ?
C11E H11C 0.9600 . ?
C1C N1C 1.328(3) . ?
C1C C2C 1.378(3) . ?
C1C H1C 0.9300 . ?
C2C C3C 1.395(3) . ?
C2C I1F 2.033(3) . ?
C2C I1C 2.096(3) . ?
C3C N2C 1.348(2) . ?
C3C C4C 1.476(3) . ?
C4C C9C 1.386(3) . ?
C4C C5C 1.390(3) . ?
C5C C6C 1.379(3) . ?
C5C H5C 0.9300 . ?
C6C C7C 1.374(4) . ?
C6C H6C 0.9300 . ?
C7C C8C 1.383(3) . ?
C7C H7C 0.9300 . ?
C8C O1C 1.378(3) . ?
C8C C9C 1.389(3) . ?
C9C H9C 0.9300 . ?
C10C O2C 1.383(4) . ?
C10C O1C 1.419(3) . ?
C10C H10E 0.9700 . ?
C10C H10F 0.9700 . ?
C11C O2C 1.427(5) . ?
C11C H11G 0.9600 . ?
C11C H11H 0.9600 . ?
C11C H11I 0.9600 . ?
N1C N2C 1.354(2) . ?
N1C H1NC 0.898(19) . ?

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
N1A C1A C2A 108.96(18) . . ?
N1A C1A H1A 125.5 . . ?
C2A C1A H1A 125.5 . . ?
C1A C2A C3A 105.48(18) . . ?
C1A C2A I1A 125.84(19) . . ?
C3A C2A I1A 128.1(2) . . ?
C1A C2A I1D 121.85(17) . . ?
C3A C2A I1D 132.62(18) . . ?
N2A C3A C2A 108.16(17) . . ?
N2A C3A C4A 119.72(16) . . ?
C2A C3A C4A 132.05(18) . . ?
C9A C4A C5A 119.43(19) . . ?
C9A C4A C3A 119.75(18) . . ?
C5A C4A C3A 120.72(19) . . ?
C6A C5A C4A 119.7(2) . . ?
C6A C5A H5A 120.2 . . ?
C4A C5A H5A 120.2 . . ?
C7A C6A C5A 121.2(2) . . ?
C7A C6A H6A 119.4 . . ?
C5A C6A H6A 119.4 . . ?
C6A C7A C8A 119.0(2) . . ?
C6A C7A H7A 120.5 . . ?
C8A C7A H7A 120.5 . . ?
C7A C8A O1A 125.38(19) . . ?
C7A C8A C9A 120.4(2) . . ?
O1A C8A C9A 114.24(19) . . ?
C4A C9A C8A 120.21(19) . . ?
C4A C9A H9A 119.9 . . ?
C8A C9A H9A 119.9 . . ?
O2A C10A O1A 113.1(2) . . ?
O2A C10A H10C 109.0 . . ?
O1A C10A H10C 109.0 . . ?
O2A C10A H10D 109.0 . . ?
O1A C10A H10D 109.0 . . ?
H10C C10A H10D 107.8 . . ?
O2A C11A H11D 109.5 . . ?
O2A C11A H11E 109.5 . . ?
H11D C11A H11E 109.5 . . ?
O2A C11A H11F 109.5 . . ?
H11D C11A H11F 109.5 . . ?
H11E C11A H11F 109.5 . . ?
C1A N1A N2A 108.81(18) . . ?
C1A N1A H1NA 126(3) . . ?
N2A N1A H1NA 126(3) . . ?
C3A N2A N1A 108.59(16) . . ?
C8A O1A C10A 117.86(19) . . ?
C10A O2A C11A 113.6(2) . . ?
N1B C1B C2B 108.23(18) . . ?
N1B C1B H1B 125.9 . . ?
C2B C1B H1B 125.9 . . ?
C1B C2B C3B 106.27(16) . . ?
C1B C2B I1E 125.21(18) . . ?
C3B C2B I1E 127.98(19) . . ?
C1B C2B I1B 123.44(15) . . ?
C3B C2B I1B 130.29(16) . . ?
N2B C3B C2B 107.58(17) . . ?
N2B C3B C4B 120.55(16) . . ?
C2B C3B C4B 131.86(17) . . ?
C9B C4B C5B 119.61(18) . . ?
C9B C4B C3B 119.65(17) . . ?
C5B C4B C3B 120.74(17) . . ?
C6B C5B C4B 119.3(2) . . ?
C6B C5B H5B 120.3 . . ?
C4B C5B H5B 120.3 . . ?
C5B C6B C7B 121.35(19) . . ?
C5B C6B H6B 119.3 . . ?
C7B C6B H6B 119.3 . . ?
C6B C7B C8B 119.6(2) . . ?
C6B C7B H7B 120.2 . . ?
C8B C7B H7B 120.2 . . ?
O1E C8B C7B 122.0(10) . . ?
C7B C8B O1B 126.0(5) . . ?
O1E C8B C9B 117.2(10) . . ?
C7B C8B C9B 119.92(19) . . ?
O1B C8B C9B 113.8(5) . . ?
C8B C9B C4B 120.23(18) . . ?
C8B C9B H9B 119.9 . . ?
C4B C9B H9B 119.9 . . ?
C1B N1B N2B 109.49(17) . . ?
C1B N1B H1NB 125(2) . . ?
N2B N1B H1NB 125(2) . . ?
N1B N2B C3B 108.43(15) . . ?
O2B C10B O1B 116.3(7) . . ?
O2B C10B H10A 108.2 . . ?
O1B C10B H10A 108.2 . . ?
O2B C10B H10B 108.2 . . ?
O1B C10B H10B 108.2 . . ?
H10A C10B H10B 107.4 . . ?
O2B C11B H11J 109.5 . . ?
O2B C11B H11K 109.5 . . ?
H11J C11B H11K 109.5 . . ?
O2B C11B H11L 109.5 . . ?
H11J C11B H11L 109.5 . . ?
H11K C11B H11L 109.5 . . ?
C8B O1B C10B 118.7(8) . . ?
C10B O2B C11B 112.9(6) . . ?
O2E C10E O1E 104.0(14) . . ?
O2E C10E H10G 110.9 . . ?
O1E C10E H10G 110.9 . . ?
O2E C10E H10H 110.9 . . ?
O1E C10E H10H 110.9 . . ?
H10G C10E H10H 109.0 . . ?
O2E C11E H11A 109.5 . . ?
O2E C11E H11B 109.5 . . ?
H11A C11E H11B 109.5 . . ?
O2E C11E H11C 109.5 . . ?
H11A C11E H11C 109.5 . . ?
H11B C11E H11C 109.5 . . ?
C8B O1E C10E 115.0(16) . . ?
C11E O2E C10E 116.2(14) . . ?
N1C C1C C2C 108.57(19) . . ?
N1C C1C H1C 125.7 . . ?
C2C C1C H1C 125.7 . . ?
C1C C2C C3C 106.01(17) . . ?
C1C C2C I1F 124.17(18) . . ?
C3C C2C I1F 129.82(16) . . ?
C1C C2C I1C 125.21(17) . . ?
C3C C2C I1C 128.21(15) . . ?
N2C C3C C2C 107.89(16) . . ?
N2C C3C C4C 120.30(18) . . ?
C2C C3C C4C 131.81(17) . . ?
C9C C4C C5C 119.17(19) . . ?
C9C C4C C3C 120.07(17) . . ?
C5C C4C C3C 120.8(2) . . ?
C6C C5C C4C 119.8(2) . . ?
C6C C5C H5C 120.1 . . ?
C4C C5C H5C 120.1 . . ?
C7C C6C C5C 121.2(2) . . ?
C7C C6C H6C 119.4 . . ?
C5C C6C H6C 119.4 . . ?
C6C C7C C8C 119.4(2) . . ?
C6C C7C H7C 120.3 . . ?
C8C C7C H7C 120.3 . . ?
O1C C8C C7C 124.8(2) . . ?
O1C C8C C9C 115.2(2) . . ?
C7C C8C C9C 120.0(2) . . ?
C4C C9C C8C 120.4(2) . . ?
C4C C9C H9C 119.8 . . ?
C8C C9C H9C 119.8 . . ?
O2C C10C O1C 113.0(2) . . ?
O2C C10C H10E 109.0 . . ?
O1C C10C H10E 109.0 . . ?
O2C C10C H10F 109.0 . . ?
O1C C10C H10F 109.0 . . ?
H10E C10C H10F 107.8 . . ?
O2C C11C H11G 109.5 . . ?
O2C C11C H11H 109.5 . . ?
H11G C11C H11H 109.5 . . ?
O2C C11C H11I 109.5 . . ?
H11G C11C H11I 109.5 . . ?
H11H C11C H11I 109.5 . . ?
C1C N1C N2C 109.43(16) . . ?
C1C N1C H1NC 131(3) . . ?
N2C N1C H1NC 119(3) . . ?
C3C N2C N1C 108.10(16) . . ?
C8C O1C C10C 117.8(2) . . ?
C10C O2C C11C 111.9(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
N1A C1A C2A C3A -0.1(3) . . . . ?
N1A C1A C2A I1A 171.6(3) . . . . ?
N1A C1A C2A I1D -177.7(2) . . . . ?
C1A C2A C3A N2A -0.1(2) . . . . ?
I1A C2A C3A N2A -171.5(3) . . . . ?
I1D C2A C3A N2A 177.1(2) . . . . ?
C1A C2A C3A C4A -176.9(2) . . . . ?
I1A C2A C3A C4A 11.6(4) . . . . ?
I1D C2A C3A C4A 0.2(4) . . . . ?
N2A C3A C4A C9A 35.7(3) . . . . ?
C2A C3A C4A C9A -147.8(2) . . . . ?
N2A C3A C4A C5A -140.6(2) . . . . ?
C2A C3A C4A C5A 35.9(3) . . . . ?
C9A C4A C5A C6A -1.6(3) . . . . ?
C3A C4A C5A C6A 174.68(19) . . . . ?
C4A C5A C6A C7A -0.6(3) . . . . ?
C5A C6A C7A C8A 2.1(3) . . . . ?
C6A C7A C8A O1A -179.9(2) . . . . ?
C6A C7A C8A C9A -1.3(3) . . . . ?
C5A C4A C9A C8A 2.4(3) . . . . ?
C3A C4A C9A C8A -173.96(17) . . . . ?
C7A C8A C9A C4A -0.9(3) . . . . ?
O1A C8A C9A C4A 177.83(18) . . . . ?
C2A C1A N1A N2A 0.3(3) . . . . ?
C2A C3A N2A N1A 0.2(2) . . . . ?
C4A C3A N2A N1A 177.52(17) . . . . ?
C1A N1A N2A C3A -0.3(2) . . . . ?
C7A C8A O1A C10A -1.7(3) . . . . ?
C9A C8A O1A C10A 179.6(2) . . . . ?
O2A C10A O1A C8A 72.8(3) . . . . ?
O1A C10A O2A C11A 71.8(3) . . . . ?
N1B C1B C2B C3B 0.0(3) . . . . ?
N1B C1B C2B I1E -172.2(2) . . . . ?
N1B C1B C2B I1B 179.47(18) . . . . ?
C1B C2B C3B N2B -0.1(2) . . . . ?
I1E C2B C3B N2B 171.8(2) . . . . ?
I1B C2B C3B N2B -179.52(19) . . . . ?
C1B C2B C3B C4B -178.7(2) . . . . ?
I1E C2B C3B C4B -6.8(4) . . . . ?
I1B C2B C3B C4B 1.9(4) . . . . ?
N2B C3B C4B C9B -41.2(3) . . . . ?
C2B C3B C4B C9B 137.2(2) . . . . ?
N2B C3B C4B C5B 139.0(2) . . . . ?
C2B C3B C4B C5B -42.6(3) . . . . ?
C9B C4B C5B C6B -1.3(3) . . . . ?
C3B C4B C5B C6B 178.53(19) . . . . ?
C4B C5B C6B C7B 1.9(3) . . . . ?
C5B C6B C7B C8B -0.6(4) . . . . ?
C6B C7B C8B O1E 167.7(10) . . . . ?
C6B C7B C8B O1B -175.4(5) . . . . ?
C6B C7B C8B C9B -1.4(3) . . . . ?
O1E C8B C9B C4B -167.7(9) . . . . ?
C7B C8B C9B C4B 2.0(3) . . . . ?
O1B C8B C9B C4B 176.7(4) . . . . ?
C5B C4B C9B C8B -0.6(3) . . . . ?
C3B C4B C9B C8B 179.55(18) . . . . ?
C2B C1B N1B N2B 0.1(3) . . . . ?
C1B N1B N2B C3B -0.2(2) . . . . ?
C2B C3B N2B N1B 0.2(2) . . . . ?
C4B C3B N2B N1B 178.96(17) . . . . ?
C7B C8B O1B C10B -7.2(9) . . . . ?
C9B C8B O1B C10B 178.5(6) . . . . ?
O2B C10B O1B C8B -65.8(10) . . . . ?
O1B C10B O2B C11B -77.8(9) . . . . ?
C7B C8B O1E C10E 16.6(17) . . . . ?
C9B C8B O1E C10E -174.0(12) . . . . ?
O2E C10E O1E C8B -178.2(16) . . . . ?
O1E C10E O2E C11E 70.0(18) . . . . ?
N1C C1C C2C C3C -0.3(2) . . . . ?
N1C C1C C2C I1F 179.9(3) . . . . ?
N1C C1C C2C I1C -172.2(2) . . . . ?
C1C C2C C3C N2C -0.2(2) . . . . ?
I1F C2C C3C N2C 179.5(3) . . . . ?
I1C C2C C3C N2C 171.3(2) . . . . ?
C1C C2C C3C C4C -179.3(2) . . . . ?
I1F C2C C3C C4C 0.4(4) . . . . ?
I1C C2C C3C C4C -7.8(4) . . . . ?
N2C C3C C4C C9C -35.1(3) . . . . ?
C2C C3C C4C C9C 143.9(2) . . . . ?
N2C C3C C4C C5C 143.8(2) . . . . ?
C2C C3C C4C C5C -37.1(3) . . . . ?
C9C C4C C5C C6C -0.5(3) . . . . ?
C3C C4C C5C C6C -179.4(2) . . . . ?
C4C C5C C6C C7C 1.1(4) . . . . ?
C5C C6C C7C C8C -0.5(4) . . . . ?
C6C C7C C8C O1C 179.0(2) . . . . ?
C6C C7C C8C C9C -0.8(3) . . . . ?
C5C C4C C9C C8C -0.8(3) . . . . ?
C3C C4C C9C C8C 178.15(19) . . . . ?
O1C C8C C9C C4C -178.41(19) . . . . ?
C7C C8C C9C C4C 1.4(3) . . . . ?
C2C C1C N1C N2C 0.7(2) . . . . ?
C2C C3C N2C N1C 0.6(2) . . . . ?
C4C C3C N2C N1C 179.89(17) . . . . ?
C1C N1C N2C C3C -0.8(2) . . . . ?
C7C C8C O1C C10C 15.4(3) . . . . ?
C9C C8C O1C C10C -164.7(2) . . . . ?
O2C C10C O1C C8C -75.6(3) . . . . ?
O1C C10C O2C C11C -69.8(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
N1A H1NA N2C 0.92(4) 1.99(4) 2.890(3) 167(4) . yes
N1B H1NB N2A 0.89(4) 1.99(4) 2.879(2) 172(4) . yes
N1C H1NC N2B 0.898(19) 2.05(2) 2.932(2) 168(4) . yes

_refine_diff_density_max         0.425
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.053

