# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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 2262134'
loop_
_audit_author_name
_audit_author_address
'HRIZI chakib'
;Gabes university, Tunisia
Tunisia
;
_audit_update_record             
;
2024-03-23 deposited with the CCDC.	2024-04-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H20 I3 N'
_chemical_formula_weight         510.95

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'
I I -0.4742 1.8119 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

_cell_length_a                   14.5312(6)
_cell_length_b                   13.8795(5)
_cell_length_c                   15.1632(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3058.2(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2284
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      34.17

_exptl_crystal_description       block
_exptl_crystal_colour            red-brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.219
_exptl_crystal_F_000             1872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    6.099
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.279
_exptl_absorpt_correction_T_max  0.511
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(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 area detector'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            14335
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.941
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_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             3098
_reflns_number_gt                2284
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  ?
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0158P)²+4.3072P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00216(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3098
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0257
_refine_ls_wR_factor_ref         0.0610
_refine_ls_wR_factor_gt          0.0510
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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
I1 I 0.29798(4) 0.2500 0.47641(4) 0.07481(18) Uani 1 2 d S T P . .
I2 I 0.49548(3) 0.2500 0.50905(3) 0.06173(15) Uani 1 2 d S T P . .
I3 I 0.69556(4) 0.2500 0.54378(3) 0.06853(17) Uani 1 2 d S T P . .
I4A I 1.00023(6) 0.2500 0.72235(5) 0.0804(2) Uani 0.95 2 d S T P A 1
I5A I 1.01300(5) 0.2500 0.53215(5) 0.06427(19) Uani 0.95 2 d S T P A 1
I6A I 1.03379(7) 0.2500 0.33640(5) 0.0823(3) Uani 0.95 2 d S T P A 1
I4B I 0.9886(13) 0.2500 0.6801(7) 0.081(5) Uani 0.05 2 d S T P B 2
I5B I 1.0048(10) 0.2500 0.4895(6) 0.047(3) Uani 0.05 2 d S T P B 2
I6B I 1.0222(12) 0.2500 0.2955(6) 0.051(3) Uani 0.05 2 d S T P B 2
N1 N 0.7586(2) 0.0089(2) 0.2939(2) 0.0502(9) Uani 1 1 d . . . . .
C1 C 0.7173(4) -0.0658(4) 0.2339(3) 0.0747(15) Uani 1 1 d . . . . .
H1A H 0.6812 -0.1103 0.2691 0.090 Uiso 1 1 calc R U . . .
H1B H 0.7667 -0.1022 0.2066 0.090 Uiso 1 1 calc R U . . .
C2 C 0.6562(5) -0.0242(5) 0.1617(4) 0.098(2) Uani 1 1 d . . . . .
H2A H 0.6323 -0.0756 0.1261 0.147 Uiso 1 1 calc R U . . .
H2B H 0.6061 0.0106 0.1880 0.147 Uiso 1 1 calc R U . . .
H2C H 0.6917 0.0187 0.1254 0.147 Uiso 1 1 calc R U . . .
C3 C 0.6846(3) 0.0643(4) 0.3420(3) 0.0678(14) Uani 1 1 d . . . . .
H3A H 0.7138 0.1139 0.3773 0.081 Uiso 1 1 calc R U . . .
H3B H 0.6462 0.0963 0.2986 0.081 Uiso 1 1 calc R U . . .
C4 C 0.6236(4) 0.0050(4) 0.4011(4) 0.0823(17) Uani 1 1 d . . . . .
H4A H 0.5789 0.0461 0.4287 0.123 Uiso 1 1 calc R U . . .
H4B H 0.5927 -0.0432 0.3667 0.123 Uiso 1 1 calc R U . . .
H4C H 0.6604 -0.0257 0.4456 0.123 Uiso 1 1 calc R U . . .
C5 C 0.8198(4) -0.0437(4) 0.3578(3) 0.0725(14) Uani 1 1 d . . . . .
H5A H 0.7823 -0.0893 0.3904 0.087 Uiso 1 1 calc R U . . .
H5B H 0.8645 -0.0805 0.3243 0.087 Uiso 1 1 calc R U . . .
C6 C 0.8706(4) 0.0176(4) 0.4227(4) 0.0884(18) Uani 1 1 d . . . . .
H6A H 0.9074 -0.0226 0.4602 0.133 Uiso 1 1 calc R U . . .
H6B H 0.9097 0.0619 0.3917 0.133 Uiso 1 1 calc R U . . .
H6C H 0.8273 0.0530 0.4579 0.133 Uiso 1 1 calc R U . . .
C7 C 0.8126(4) 0.0822(4) 0.2414(3) 0.0762(15) Uani 1 1 d . . . . .
H7A H 0.8384 0.1292 0.2818 0.091 Uiso 1 1 calc R U . . .
H7B H 0.7708 0.1159 0.2023 0.091 Uiso 1 1 calc R U . . .
C8 C 0.8912(4) 0.0388(5) 0.1862(4) 0.108(2) Uani 1 1 d . . . . .
H8A H 0.9223 0.0892 0.1548 0.161 Uiso 1 1 calc R U . . .
H8B H 0.9340 0.0067 0.2244 0.161 Uiso 1 1 calc R U . . .
H8C H 0.8663 -0.0067 0.1448 0.161 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
I1 I2 2.9122(7) . ?
I2 I3 2.9547(7) . ?
I4A I5A 2.8900(10) . ?
I5A I6A 2.9835(10) . ?
I4B I5B 2.900(13) . ?
I5B I6B 2.952(13) . ?
N1 C1 1.504(6) . ?
N1 C5 1.504(6) . ?
N1 C3 1.510(6) . ?
N1 C7 1.511(6) . ?
C1 C2 1.524(7) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.505(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.497(7) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.539(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

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
I1 I2 I3 179.52(2) . . ?
I4A I5A I6A 177.87(4) . . ?
I4B I5B I6B 179.7(8) . . ?
C1 N1 C5 106.9(4) . . ?
C1 N1 C3 111.0(4) . . ?
C5 N1 C3 110.9(3) . . ?
C1 N1 C7 110.7(4) . . ?
C5 N1 C7 111.1(4) . . ?
C3 N1 C7 106.4(4) . . ?
N1 C1 C2 113.9(4) . . ?
N1 C1 H1A 108.8 . . ?
C2 C1 H1A 108.8 . . ?
N1 C1 H1B 108.8 . . ?
C2 C1 H1B 108.8 . . ?
H1A C1 H1B 107.7 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 N1 115.4(4) . . ?
C4 C3 H3A 108.4 . . ?
N1 C3 H3A 108.4 . . ?
C4 C3 H3B 108.4 . . ?
N1 C3 H3B 108.4 . . ?
H3A C3 H3B 107.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 N1 116.1(4) . . ?
C6 C5 H5A 108.3 . . ?
N1 C5 H5A 108.3 . . ?
C6 C5 H5B 108.3 . . ?
N1 C5 H5B 108.3 . . ?
H5A C5 H5B 107.4 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C7 C8 114.1(5) . . ?
N1 C7 H7A 108.7 . . ?
C8 C7 H7A 108.7 . . ?
N1 C7 H7B 108.7 . . ?
C8 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

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 -177.4(5) . . . . ?
C3 N1 C1 C2 61.5(5) . . . . ?
C7 N1 C1 C2 -56.3(6) . . . . ?
C1 N1 C3 C4 61.3(5) . . . . ?
C5 N1 C3 C4 -57.4(6) . . . . ?
C7 N1 C3 C4 -178.3(5) . . . . ?
C1 N1 C5 C6 178.3(5) . . . . ?
C3 N1 C5 C6 -60.6(6) . . . . ?
C7 N1 C5 C6 57.5(6) . . . . ?
C1 N1 C7 C8 -58.4(6) . . . . ?
C5 N1 C7 C8 60.1(6) . . . . ?
C3 N1 C7 C8 -179.1(5) . . . . ?

_refine_diff_density_max         0.795
_refine_diff_density_min         -0.763
_refine_diff_density_rms         0.081

####################################################################### 
# 
# 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 2262254'
loop_
_audit_author_name
_audit_author_address
'HRIZI chakib'
;Gabes university, Tunisia
Tunisia
;
_audit_update_record             
;
2024-03-23 deposited with the CCDC.	2024-04-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H12 I3 N2 O0.50'
_chemical_formula_weight         512.89

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'
I I -0.4742 1.8119 '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           13
_space_group_name_H-M_alt        'P 2/c'
_space_group_name_Hall           '-P 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, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   16.9466(12)
_cell_length_b                   6.0287(4)
_cell_length_c                   13.6214(11)
_cell_angle_alpha                90
_cell_angle_beta                 97.621(4)
_cell_angle_gamma                90
_cell_volume                     1379.35(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1772
_cell_measurement_theta_min      3.23
_cell_measurement_theta_max      44.12

_exptl_crystal_description       plate
_exptl_crystal_colour            black/dark-red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.470
_exptl_crystal_F_000             924
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.313
_exptl_crystal_size_mid          0.288
_exptl_crystal_size_min          0.17
_exptl_absorpt_coefficient_mu    6.766
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.138
_exptl_absorpt_correction_T_max  0.317
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(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 area detector'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            9572
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.018
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2709
_reflns_number_gt                1772
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0264P)²+7.6179P] 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         2709
_refine_ls_number_parameters     121
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1157
_refine_ls_wR_factor_gt          0.0861
_refine_ls_goodness_of_fit_ref   1.197
_refine_ls_restrained_S_all      1.196
_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
I1 I 0.59190(4) -0.34554(12) 0.17842(5) 0.0686(2) Uani 1 1 d . . . . .
I2 I 0.75275(3) -0.33237(9) 0.13122(4) 0.05315(19) Uani 1 1 d . . . . .
I3 I 0.91907(4) -0.33553(14) 0.08628(6) 0.0814(3) Uani 1 1 d . . . . .
O1 O 1.0000 0.221(2) 0.2500 0.104(4) Uani 1 2 d DS T P . .
H1A H 1.02(2) 0.23(4) 0.312(6) 0.156 Uiso 0.5 1 d D U P . .
H1B H 0.977(17) 0.34(2) 0.235(19) 0.156 Uiso 0.5 1 d D U P . .
N1 N 0.8726(5) 0.0085(14) 0.3367(6) 0.064(2) Uani 1 1 d . . . . .
H1 H 0.9193 0.0108 0.3186 0.076 Uiso 1 1 calc R U . . .
N2 N 0.6485(4) -0.0078(12) 0.4182(6) 0.0532(18) Uani 1 1 d . . . . .
C1 C 0.7211(5) -0.0031(14) 0.3924(6) 0.048(2) Uani 1 1 d . . . . .
C2 C 0.7449(5) 0.1624(15) 0.3295(7) 0.056(2) Uani 1 1 d . . . . .
H2 H 0.7089 0.2717 0.3049 0.067 Uiso 1 1 calc R U . . .
C3 C 0.8191(6) 0.1644(18) 0.3046(8) 0.067(3) Uani 1 1 d . . . . .
H3 H 0.8336 0.2772 0.2640 0.080 Uiso 1 1 calc R U . . .
C4 C 0.8528(6) -0.1507(17) 0.3971(8) 0.065(3) Uani 1 1 d . . . . .
H4 H 0.8908 -0.2560 0.4205 0.078 Uiso 1 1 calc R U . . .
C5 C 0.7801(5) -0.1639(15) 0.4253(7) 0.055(2) Uani 1 1 d . . . . .
H5 H 0.7682 -0.2787 0.4665 0.067 Uiso 1 1 calc R U . . .
C6 C 0.5878(6) 0.1517(16) 0.3810(8) 0.065(3) Uani 1 1 d . . . . .
H6A H 0.5950 0.2856 0.4193 0.097 Uiso 1 1 calc R U . . .
H6B H 0.5361 0.0910 0.3862 0.097 Uiso 1 1 calc R U . . .
H6C H 0.5919 0.1841 0.3129 0.097 Uiso 1 1 calc R U . . .
C7 C 0.6254(6) -0.1759(16) 0.4851(8) 0.066(3) Uani 1 1 d . . . . .
H7A H 0.5710 -0.1529 0.4951 0.100 Uiso 1 1 calc R U . . .
H7B H 0.6308 -0.3202 0.4569 0.100 Uiso 1 1 calc R U . . .
H7C H 0.6590 -0.1659 0.5474 0.100 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
I1 I2 2.8835(9) . ?
I2 I3 2.9627(9) . ?
O1 H1A 0.85(2) . ?
O1 H1B 0.85(2) . ?
N1 C4 1.336(12) . ?
N1 C3 1.338(12) . ?
N1 H1 0.8600 . ?
N2 C1 1.324(11) . ?
N2 C6 1.450(11) . ?
N2 C7 1.451(11) . ?
C1 C2 1.408(12) . ?
C1 C5 1.423(12) . ?
C2 C3 1.345(13) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 C5 1.340(13) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?

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
I1 I2 I3 177.83(3) . . ?
H1A O1 H1B 104(5) . . ?
C4 N1 C3 119.4(8) . . ?
C4 N1 H1 120.3 . . ?
C3 N1 H1 120.3 . . ?
C1 N2 C6 122.3(8) . . ?
C1 N2 C7 121.3(7) . . ?
C6 N2 C7 116.4(7) . . ?
N2 C1 C2 121.9(8) . . ?
N2 C1 C5 122.7(8) . . ?
C2 C1 C5 115.4(8) . . ?
C3 C2 C1 120.8(9) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
N1 C3 C2 121.8(10) . . ?
N1 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
N1 C4 C5 122.3(9) . . ?
N1 C4 H4 118.8 . . ?
C5 C4 H4 118.8 . . ?
C4 C5 C1 120.3(9) . . ?
C4 C5 H5 119.9 . . ?
C1 C5 H5 119.9 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

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
C6 N2 C1 C2 2.2(13) . . . . ?
C7 N2 C1 C2 -178.4(8) . . . . ?
C6 N2 C1 C5 -177.4(8) . . . . ?
C7 N2 C1 C5 1.9(13) . . . . ?
N2 C1 C2 C3 179.7(9) . . . . ?
C5 C1 C2 C3 -0.6(13) . . . . ?
C4 N1 C3 C2 -1.7(15) . . . . ?
C1 C2 C3 N1 1.2(16) . . . . ?
C3 N1 C4 C5 1.7(15) . . . . ?
N1 C4 C5 C1 -1.2(15) . . . . ?
N2 C1 C5 C4 -179.7(9) . . . . ?
C2 C1 C5 C4 0.6(13) . . . . ?

_refine_diff_density_max         1.292
_refine_diff_density_min         -1.014
_refine_diff_density_rms         0.142

