# Electronic Supplementary Material (ESI) for Sustainable Energy & Fuels.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_nani_diaobu2i23
_database_code_depnum_ccdc_archive 'CCDC 2099189'
loop_
_audit_author_name
_audit_author_address
'NANI GOPAL GHOSH'
;IISER Kolkata
India
;
_audit_update_record             
;
2021-07-26 deposited with the CCDC.	2022-04-12 downloaded from the CCDC.
;
_audit_creation_date             2021-07-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H22 I2 O4'
_chemical_formula_sum            'C22 H22 I2 O4'
_chemical_formula_weight         604.19
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H I O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   10.4919(3)
_cell_length_b                   27.9599(10)
_cell_length_c                   14.2253(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4173.0(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5661
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      66.0700
_cell_measurement_theta_min      3.1660
_shelx_estimated_absorpt_T_max   0.890
_shelx_estimated_absorpt_T_min   0.448
_exptl_absorpt_coefficient_mu    23.888
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear reddish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.923
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2336
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.005
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7724
_diffrn_reflns_point_group_measured_fraction_full 0.909
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_theta_full        66.243
_diffrn_reflns_theta_max         66.243
_diffrn_reflns_theta_min         5.473
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      1.00  81.00   1.00    1.00    --   26.33 -99.00 -60.00   80
  2  ω    -12.00 102.00   1.00    1.00    --   26.33  57.00  60.00  114
  3  ω    -12.00 102.00   1.00    1.00    --   26.33  57.00 -60.00  114
  4  ω    100.00 153.00   1.00    2.50    --   67.17 111.00  30.00   53
  5  ω     79.00 150.00   1.00    2.50    --   67.17 151.00 -82.00   71
  6  ω     23.00  49.00   1.00    2.50    --   67.17  78.00 119.67   26
  7  ω    100.00 153.00   1.00    2.50    --   67.17 111.00 -90.00   53
  8  ω     20.00 147.00   1.00    2.50    --   67.17  45.00  30.00  127
  9  ω     96.00 178.00   1.00    3.00    --  108.00 122.00 116.00   82
 10  ω     98.00 178.00   1.00    3.00    --  108.00 117.00-149.00   80
 11  ω    101.00 178.00   1.00    3.00    --  108.00 104.00  90.00   77
 12  ω    101.00 178.00   1.00    3.00    --  108.00 104.00-180.00   77
 13  ω     69.00 178.00   1.00    3.00    --  108.00  54.00-120.00  109
 14  ω     25.00 178.00   1.00    3.00    --  108.00 -32.00  60.00  153
 15  ω     67.00 178.00   1.00    3.00    --  108.00  73.00 -16.52  111
 16  ω     21.00 113.00   1.00    3.00    --  108.00-104.00 120.00   92
 17  ω     86.00 178.00   1.00    3.00    --  108.00 138.00-150.00   92
 18  ω     86.00 178.00   1.00    3.00    --  108.00 138.00 120.00   92
 19  ω     86.00 178.00   1.00    3.00    --  108.00 138.00  90.00   92
 20  ω    -12.00 102.00   1.00    1.00    --   26.33  57.00-180.00  114
 21  ω    -50.00  64.00   1.00    1.00    --   26.33 -57.00  60.00  114
 22  ω    100.00 153.00   1.00    2.50    --   67.17 111.00 120.00   53
 23  ω     20.00 147.00   1.00    2.50    --   67.17  45.00 -60.00  127
 24  ω     30.00 144.00   1.00    2.50    --   67.17  61.00  90.00  114
 25  ω     30.00 144.00   1.00    2.50    --   67.17  61.00-180.00  114
 26  ω     65.00 178.00   1.00    3.00    --  108.00  77.00  60.00  113
 27  ω    101.00 178.00   1.00    3.00    --  108.00 104.00  30.00   77
 28  ω     65.00 178.00   1.00    3.00    --  108.00  77.00 -60.00  113
 29  ω     65.00 178.00   1.00    3.00    --  108.00  77.00 -90.00  113
 30  ω     36.00 178.00   1.00    3.00    --  108.00  32.00-180.00  142
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1406343000
_diffrn_orient_matrix_UB_12      0.0139897000
_diffrn_orient_matrix_UB_13      0.0136577000
_diffrn_orient_matrix_UB_21      0.0349256000
_diffrn_orient_matrix_UB_22      0.0531012000
_diffrn_orient_matrix_UB_23      -0.0142282000
_diffrn_orient_matrix_UB_31      -0.0227449000
_diffrn_orient_matrix_UB_32      -0.0053052000
_diffrn_orient_matrix_UB_33      -0.1064607000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.749
_reflns_Friedel_fraction_full    0.815
_reflns_Friedel_fraction_max     0.814
_reflns_number_gt                1671
_reflns_number_total             1677
_reflns_odcompleteness_completeness 97.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         1.039
_refine_diff_density_min         -1.265
_refine_diff_density_rms         0.132
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.001(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1677
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0411
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0946P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1037
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 -0.13937(5) 0.30407(2) 0.54335(7) 0.0189(3) Uani 1 1 d . . . . .
O2 O 0.4360(5) 0.36058(17) 0.5283(5) 0.0147(13) Uani 1 1 d . . . . .
O1 O 0.4773(6) 0.27550(17) 0.4508(5) 0.0207(13) Uani 1 1 d . . . . .
C5 C 0.1502(8) 0.2866(3) 0.5136(6) 0.0124(19) Uani 1 1 d . . . . .
C8 C 0.4719(8) 0.4107(2) 0.5314(7) 0.0142(15) Uani 1 1 d . . . . .
H8A H 0.444213 0.425203 0.589942 0.017 Uiso 1 1 calc R U . . .
H8B H 0.433500 0.428048 0.479553 0.017 Uiso 1 1 calc R U . . .
C4 C 0.0553(8) 0.3201(3) 0.5315(8) 0.0172(16) Uani 1 1 d . . . . .
C9 C 0.6156(9) 0.4119(3) 0.5239(8) 0.017(2) Uani 1 1 d . . . . .
H9A H 0.642028 0.392386 0.471017 0.021 Uiso 1 1 calc R U . . .
H9B H 0.652168 0.398104 0.580423 0.021 Uiso 1 1 calc R U . . .
C3 C 0.0890(8) 0.3673(3) 0.5477(9) 0.0176(17) Uani 1 1 d . . . . .
H3 H 0.025479 0.389564 0.560810 0.021 Uiso 1 1 calc R U . . .
C2 C 0.2145(8) 0.3823(2) 0.5449(7) 0.0164(16) Uani 1 1 d . . . . .
H2 H 0.234357 0.414344 0.553936 0.020 Uiso 1 1 calc R U . . .
C6 C 0.2787(10) 0.3005(3) 0.5127(6) 0.014(2) Uani 1 1 d . . . . .
C7 C 0.3791(8) 0.2647(3) 0.4882(7) 0.0124(18) Uani 1 1 d . . . . .
C1 C 0.3111(9) 0.3492(3) 0.5286(7) 0.0138(16) Uani 1 1 d . . . . .
C11 C 0.8098(9) 0.4624(3) 0.5046(8) 0.025(2) Uani 1 1 d . . . . .
H11A H 0.835894 0.442174 0.453600 0.037 Uiso 1 1 calc R U . . .
H11B H 0.845105 0.450589 0.562343 0.037 Uiso 1 1 calc R U . . .
H11C H 0.839734 0.494388 0.493655 0.037 Uiso 1 1 calc R U . . .
C10 C 0.6670(9) 0.4626(3) 0.5111(7) 0.0182(19) Uani 1 1 d . . . . .
H10A H 0.631492 0.476410 0.454304 0.022 Uiso 1 1 calc R U . . .
H10B H 0.640747 0.482264 0.563857 0.022 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 C4 2.097(9) . ?
O2 C8 1.453(8) . ?
O2 C1 1.350(11) . ?
O1 C7 1.198(11) . ?
C5 C4 1.390(12) . ?
C5 C6 1.402(13) . ?
C5 C7 1.512(11) 14 ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.512(11) . ?
C4 C3 1.388(12) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.528(12) . ?
C3 H3 0.9300 . ?
C3 C2 1.382(13) . ?
C2 H2 0.9300 . ?
C2 C1 1.392(12) . ?
C6 C7 1.493(12) . ?
C6 C1 1.422(11) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C11 C10 1.501(13) . ?
C10 H10A 0.9700 . ?
C10 H10B 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
C1 O2 C8 118.7(6) . . ?
C4 C5 C6 120.3(8) . . ?
C4 C5 C7 122.5(8) . 14 ?
C6 C5 C7 117.1(7) . 14 ?
O2 C8 H8A 110.5 . . ?
O2 C8 H8B 110.5 . . ?
O2 C8 C9 106.0(6) . . ?
H8A C8 H8B 108.7 . . ?
C9 C8 H8A 110.5 . . ?
C9 C8 H8B 110.5 . . ?
C5 C4 I1 124.7(6) . . ?
C3 C4 I1 116.0(6) . . ?
C3 C4 C5 119.2(8) . . ?
C8 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
C8 C9 C10 112.3(7) . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C4 C3 H3 119.1 . . ?
C2 C3 C4 121.7(7) . . ?
C2 C3 H3 119.1 . . ?
C3 C2 H2 120.1 . . ?
C3 C2 C1 119.9(7) . . ?
C1 C2 H2 120.1 . . ?
C5 C6 C7 119.7(7) . . ?
C5 C6 C1 119.5(8) . . ?
C1 C6 C7 120.6(9) . . ?
O1 C7 C5 121.3(7) . 14 ?
O1 C7 C6 122.9(7) . . ?
C6 C7 C5 115.8(7) . 14 ?
O2 C1 C2 123.4(7) . . ?
O2 C1 C6 117.3(8) . . ?
C2 C1 C6 119.3(8) . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C11 C10 C9 110.9(8) . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?

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
I1 C4 C3 C2 178.0(8) . . . . ?
O2 C8 C9 C10 171.3(8) . . . . ?
C5 C4 C3 C2 1.1(17) . . . . ?
C5 C6 C7 O1 149.9(9) . . . . ?
C5 C6 C7 C5 -30.1(11) . . . 14 ?
C5 C6 C1 O2 179.1(8) . . . . ?
C5 C6 C1 C2 0.1(14) . . . . ?
C8 O2 C1 C2 -9.4(14) . . . . ?
C8 O2 C1 C6 171.7(8) . . . . ?
C8 C9 C10 C11 179.6(9) . . . . ?
C4 C5 C6 C7 -176.7(9) . . . . ?
C4 C5 C6 C1 -1.1(13) . . . . ?
C4 C3 C2 C1 -2.2(17) . . . . ?
C3 C2 C1 O2 -177.4(8) . . . . ?
C3 C2 C1 C6 1.5(15) . . . . ?
C6 C5 C4 I1 -176.1(7) . . . . ?
C6 C5 C4 C3 0.5(15) . . . . ?
C7 C5 C4 I1 8.0(14) 14 . . . ?
C7 C5 C4 C3 -175.4(10) 14 . . . ?
C7 C5 C6 C7 -0.6(10) 14 . . . ?
C7 C5 C6 C1 175.0(8) 14 . . . ?
C7 C6 C1 O2 -5.4(12) . . . . ?
C7 C6 C1 C2 175.6(9) . . . . ?
C1 O2 C8 C9 -176.4(8) . . . . ?
C1 C6 C7 O1 -25.7(14) . . . . ?
C1 C6 C7 C5 154.4(8) . . . 14 ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.536
_oxdiff_exptl_absorpt_empirical_full_min 0.533
