# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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 2194662'
loop_
_audit_author_name
_audit_author_address
'Ranjan Patra'
;Amity Institute of Click Chemistry Research and Studies
India
;
_audit_update_record             
;
2022-08-04 deposited with the CCDC.	2023-06-20 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            'C23 H16 I2 O3'
_chemical_formula_weight         594.16

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'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   8.1476(5)
_cell_length_b                   9.0775(6)
_cell_length_c                   27.2326(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2014.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9488
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      28.37

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.959
_exptl_crystal_F_000             1136
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.144
_shelx_estimated_absorpt_T_min   0.452
_shelx_estimated_absorpt_T_max   0.744
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8402
_exptl_absorpt_correction_T_max  0.9425
_exptl_absorpt_process_details   'SADABS 2.05 (Sheldrick, 2002)'
_exptl_absorpt_special_details   
; 
 ? 
;
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32141
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.913
_diffrn_reflns_theta_max         28.361
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5019
_reflns_number_gt                4756
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.746
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    1.000

_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       'Bruker APEX'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'SHELXL 5.1, XP (Sheldrick, 1994)'
_computing_publication_material  SHELXS-97
_refine_special_details          
;
 Refined as a 2-component inversion 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)+1.4157P] 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 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.44(2)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         5019
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0216
_refine_ls_R_factor_gt           0.0190
_refine_ls_wR_factor_ref         0.0403
_refine_ls_wR_factor_gt          0.0389
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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 0.1934(4) 0.6804(4) 0.51852(12) 0.0113(7) Uani 1 1 d . . . . .
H1 H 0.314428 0.684444 0.512613 0.014 Uiso 1 1 calc R U . . .
C2 C 0.1626(4) 0.6112(4) 0.56921(13) 0.0115(7) Uani 1 1 d . . . . .
H2 H 0.059218 0.551936 0.568349 0.014 Uiso 1 1 calc R U . . .
C3 C 0.1374(4) 0.7461(4) 0.60039(14) 0.0107(7) Uani 1 1 d . . . . .
C4 C 0.1183(4) 0.8666(4) 0.56956(13) 0.0107(7) Uani 1 1 d . . . . .
C5 C 0.0871(4) 1.0074(4) 0.58680(13) 0.0123(7) Uani 1 1 d . . . . .
C6 C 0.0760(5) 1.0281(4) 0.63724(13) 0.0132(7) Uani 1 1 d . . . . .
H6 H 0.057741 1.123719 0.650309 0.016 Uiso 1 1 calc R U . . .
C7 C 0.0918(4) 0.9076(4) 0.66848(13) 0.0138(8) Uani 1 1 d . . . . .
C8 C 0.1228(5) 0.7659(4) 0.65088(14) 0.0127(7) Uani 1 1 d . . . . .
H8 H 0.133796 0.685088 0.672801 0.015 Uiso 1 1 calc R U . . .
C9 C 0.3065(4) 0.5125(4) 0.58384(13) 0.0113(7) Uani 1 1 d . . . . .
H9A H 0.334480 0.448074 0.555716 0.014 Uiso 1 1 calc R U . . .
H9B H 0.403140 0.575282 0.590706 0.014 Uiso 1 1 calc R U . . .
C10 C 0.2732(4) 0.4165(4) 0.62845(13) 0.0122(7) Uani 1 1 d . . . . .
C11 C 0.4121(4) 0.3243(4) 0.64673(13) 0.0128(7) Uani 1 1 d . . . . .
C12 C 0.3988(5) 0.2555(4) 0.69255(14) 0.0182(8) Uani 1 1 d . . . . .
H12 H 0.300965 0.265347 0.711265 0.022 Uiso 1 1 calc R U . . .
C13 C 0.5279(5) 0.1734(5) 0.71045(14) 0.0223(9) Uani 1 1 d . . . . .
H13 H 0.518803 0.126945 0.741599 0.027 Uiso 1 1 calc R U . . .
C14 C 0.6708(5) 0.1581(4) 0.68336(15) 0.0202(8) Uani 1 1 d . . . . .
H14 H 0.759921 0.102637 0.696158 0.024 Uiso 1 1 calc R U . . .
C15 C 0.6835(5) 0.2232(4) 0.63797(15) 0.0200(8) Uani 1 1 d . . . . .
H15 H 0.780638 0.210928 0.619115 0.024 Uiso 1 1 calc R U . . .
C16 C 0.5550(5) 0.3065(4) 0.61963(13) 0.0173(7) Uani 1 1 d . . . . .
H16 H 0.564705 0.351837 0.588316 0.021 Uiso 1 1 calc R U . . .
C17 C 0.1121(5) 0.6064(4) 0.47478(13) 0.0138(7) Uani 1 1 d . . . . .
C18 C 0.1273(4) 0.6798(4) 0.42593(13) 0.0126(7) Uani 1 1 d . . . . .
C19 C 0.0368(5) 0.6259(4) 0.38636(13) 0.0155(8) Uani 1 1 d . . . . .
H19 H -0.035212 0.544716 0.390780 0.019 Uiso 1 1 calc R U . . .
C20 C 0.0522(6) 0.6914(4) 0.34044(13) 0.0185(7) Uani 1 1 d . . . . .
H20 H -0.010836 0.655689 0.313597 0.022 Uiso 1 1 calc R U . . .
C21 C 0.1582(5) 0.8076(5) 0.33369(14) 0.0192(8) Uani 1 1 d . . . . .
H21 H 0.169395 0.850928 0.302110 0.023 Uiso 1 1 calc R U . . .
C22 C 0.2497(5) 0.8623(4) 0.37317(15) 0.0172(8) Uani 1 1 d . . . . .
H22 H 0.323327 0.942102 0.368309 0.021 Uiso 1 1 calc R U . . .
C23 C 0.2330(4) 0.8003(4) 0.41917(14) 0.0154(8) Uani 1 1 d . . . . .
H23 H 0.292811 0.838970 0.446185 0.018 Uiso 1 1 calc R U . . .
O1 O 0.1297(3) 0.8317(3) 0.52059(9) 0.0132(5) Uani 1 1 d . . . . .
O2 O 0.1392(3) 0.4167(3) 0.64897(9) 0.0150(5) Uani 1 1 d . . . . .
O3 O 0.0377(4) 0.4913(3) 0.47996(10) 0.0249(7) Uani 1 1 d . . . . .
I1 I 0.05794(3) 0.93393(2) 0.74443(2) 0.01734(6) Uani 1 1 d . . . . .
I2 I 0.05950(3) 1.18181(2) 0.53708(2) 0.01607(6) 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 O1 1.469(4) . ?
C1 C17 1.519(5) . ?
C1 C2 1.537(5) . ?
C1 H1 1.0000 . ?
C2 C3 1.504(5) . ?
C2 C9 1.529(5) . ?
C2 H2 1.0000 . ?
C3 C4 1.388(5) . ?
C3 C8 1.392(5) . ?
C4 O1 1.374(4) . ?
C4 C5 1.385(5) . ?
C5 C6 1.389(5) . ?
C5 I2 2.095(3) . ?
C6 C7 1.391(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.396(5) . ?
C7 I1 2.100(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.519(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 O2 1.226(4) . ?
C10 C11 1.493(5) . ?
C11 C16 1.388(5) . ?
C11 C12 1.400(5) . ?
C12 C13 1.378(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.374(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O3 1.216(4) . ?
C17 C18 1.493(5) . ?
C18 C19 1.394(5) . ?
C18 C23 1.404(5) . ?
C19 C20 1.390(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.376(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.399(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.380(5) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C17 106.8(3) . . ?
O1 C1 C2 106.8(3) . . ?
C17 C1 C2 116.9(3) . . ?
O1 C1 H1 108.7 . . ?
C17 C1 H1 108.7 . . ?
C2 C1 H1 108.7 . . ?
C3 C2 C9 115.8(3) . . ?
C3 C2 C1 101.4(3) . . ?
C9 C2 C1 110.4(3) . . ?
C3 C2 H2 109.7 . . ?
C9 C2 H2 109.7 . . ?
C1 C2 H2 109.6 . . ?
C4 C3 C8 119.1(3) . . ?
C4 C3 C2 108.4(3) . . ?
C8 C3 C2 132.4(3) . . ?
O1 C4 C5 123.7(3) . . ?
O1 C4 C3 113.4(3) . . ?
C5 C4 C3 122.9(3) . . ?
C4 C5 C6 118.1(3) . . ?
C4 C5 I2 119.9(3) . . ?
C6 C5 I2 122.0(3) . . ?
C5 C6 C7 119.5(3) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C6 C7 C8 122.1(3) . . ?
C6 C7 I1 120.0(3) . . ?
C8 C7 I1 117.8(3) . . ?
C3 C8 C7 118.3(3) . . ?
C3 C8 H8 120.9 . . ?
C7 C8 H8 120.9 . . ?
C10 C9 C2 114.0(3) . . ?
C10 C9 H9A 108.7 . . ?
C2 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C2 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
O2 C10 C11 121.6(3) . . ?
O2 C10 C9 121.5(3) . . ?
C11 C10 C9 116.9(3) . . ?
C16 C11 C12 119.2(3) . . ?
C16 C11 C10 121.6(3) . . ?
C12 C11 C10 119.3(3) . . ?
C13 C12 C11 119.8(4) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 120.5(4) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 120.0(4) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.2(4) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 120.4(3) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
O3 C17 C18 121.9(3) . . ?
O3 C17 C1 120.4(3) . . ?
C18 C17 C1 117.7(3) . . ?
C19 C18 C23 119.7(3) . . ?
C19 C18 C17 119.2(3) . . ?
C23 C18 C17 121.0(3) . . ?
C20 C19 C18 119.9(4) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C21 C20 C19 120.3(4) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 120.3(4) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C23 C22 C21 120.0(4) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C23 C18 119.8(4) . . ?
C22 C23 H23 120.1 . . ?
C18 C23 H23 120.1 . . ?
C4 O1 C1 106.1(3) . . ?

_refine_diff_density_max         0.423
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.076

