# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# 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_KHD591
_database_code_depnum_ccdc_archive 'CCDC 1957756'
loop_
_audit_author_name
_audit_author_address
'Hamid Reza Khavasi'
;Shahid Beheshti University
Iran
;
_audit_update_record             
;
2020-04-18 deposited with the CCDC.	2020-05-01 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            'C16 H12 I2 O4'
_chemical_formula_weight         522.06

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           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

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

_cell_length_a                   15.8426(17)
_cell_length_b                   7.9016(6)
_cell_length_c                   13.7208(14)
_cell_angle_alpha                90
_cell_angle_beta                 90.146(9)
_cell_angle_gamma                90
_cell_volume                     1717.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1860
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      27.00

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.019
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_absorpt_coefficient_mu    3.675
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.2541
_exptl_absorpt_correction_T_max  0.3331
_exptl_absorpt_process_details   'shape of crystal determined optically'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_reflns_number            4490
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.571
_diffrn_reflns_theta_max         26.993
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             1860
_reflns_number_gt                1266
_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       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0822P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1860
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1363
_refine_ls_wR_factor_gt          0.1068
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.004
_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
C1 C 0.1932(3) -0.0453(8) 0.2933(4) 0.0533(13) Uani 1 1 d . . . . .
H1 H 0.205555 0.029693 0.243051 0.064 Uiso 1 1 calc R U . . .
C2 C 0.2417(3) -0.0451(7) 0.3781(4) 0.0516(13) Uani 1 1 d . . . . .
C3 C 0.2255(4) -0.1562(7) 0.4551(4) 0.0529(14) Uani 1 1 d . . . . .
C4 C 0.1596(4) -0.2714(9) 0.4390(5) 0.0679(17) Uani 1 1 d . . . . .
H4 H 0.148685 -0.351811 0.486846 0.082 Uiso 1 1 calc R U . . .
C5 C 0.1105(4) -0.2719(9) 0.3567(5) 0.0655(17) Uani 1 1 d . . . . .
H5 H 0.066665 -0.349391 0.350207 0.079 Uiso 1 1 calc R U . . .
C6 C 0.1264(4) -0.1577(7) 0.2839(5) 0.0551(14) Uani 1 1 d . . . . .
C7 C 0.0720(4) -0.1417(8) 0.1934(4) 0.0544(14) Uani 1 1 d . . . . .
C8 C -0.0392(5) -0.2631(13) 0.1049(6) 0.095(3) Uani 1 1 d . . . . .
H8A H -0.078865 -0.354551 0.109442 0.114 Uiso 1 1 calc R U . . .
H8B H -0.069171 -0.157703 0.100637 0.114 Uiso 1 1 calc R U . . .
H8C H -0.005076 -0.277550 0.047782 0.114 Uiso 1 1 calc R U . . .
O1 O 0.0795(3) -0.0324(6) 0.1350(4) 0.0733(12) Uani 1 1 d . . . . .
O2 O 0.0151(3) -0.2621(7) 0.1919(3) 0.0823(15) Uani 1 1 d . . . . .
I1 I 0.33852(3) 0.13549(7) 0.38405(4) 0.0860(3) Uani 1 1 d . . . . .


_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
C1 C6 1.386(8) . ?
C1 C2 1.393(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.399(8) . ?
C2 I1 2.096(5) . ?
C3 C4 1.401(8) . ?
C3 C3 1.455(11) 2_556 ?
C4 C5 1.370(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.370(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.515(8) . ?
C7 O1 1.184(7) . ?
C7 O2 1.310(7) . ?
C8 O2 1.470(8) . ?
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
C6 C1 C2 119.8(5) . . ?
C6 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
C1 C2 C3 121.9(5) . . ?
C1 C2 I1 115.8(4) . . ?
C3 C2 I1 122.2(4) . . ?
C2 C3 C4 115.3(5) . . ?
C2 C3 C3 122.8(5) . 2_556 ?
C4 C3 C3 121.9(5) . 2_556 ?
C5 C4 C3 123.5(6) . . ?
C5 C4 H4 118.2 . . ?
C3 C4 H4 118.2 . . ?
C6 C5 C4 119.6(6) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C1 119.7(6) . . ?
C5 C6 C7 123.1(5) . . ?
C1 C6 C7 117.1(5) . . ?
O1 C7 O2 126.0(5) . . ?
O1 C7 C6 123.9(6) . . ?
O2 C7 C6 110.1(5) . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 O2 C8 114.7(6) . . ?

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 C1 C2 C3 0.3(9) . . . . ?
C6 C1 C2 I1 -178.4(4) . . . . ?
C1 C2 C3 C4 2.5(9) . . . . ?
I1 C2 C3 C4 -178.9(5) . . . . ?
C1 C2 C3 C3 -179.0(6) . . . 2_556 ?
I1 C2 C3 C3 -0.3(8) . . . 2_556 ?
C2 C3 C4 C5 -3.5(10) . . . . ?
C3 C3 C4 C5 178.0(7) 2_556 . . . ?
C3 C4 C5 C6 1.6(11) . . . . ?
C4 C5 C6 C1 1.5(10) . . . . ?
C4 C5 C6 C7 -175.9(6) . . . . ?
C2 C1 C6 C5 -2.4(9) . . . . ?
C2 C1 C6 C7 175.2(5) . . . . ?
C5 C6 C7 O1 171.7(7) . . . . ?
C1 C6 C7 O1 -5.8(9) . . . . ?
C5 C6 C7 O2 -6.4(9) . . . . ?
C1 C6 C7 O2 176.1(5) . . . . ?
O1 C7 O2 C8 4.4(10) . . . . ?
C6 C7 O2 C8 -177.6(6) . . . . ?

_refine_diff_density_max         0.832
_refine_diff_density_min         -0.622
_refine_diff_density_rms         0.134

