# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_Reduced_10
_database_code_depnum_ccdc_archive 'CCDC 2329091'
loop_
_audit_author_name
_audit_author_address
'Santanu Mukherjee'
;Indian Institute of Science Bangalore
India
;
_audit_update_record             
;
2024-01-29 deposited with the CCDC.	2024-07-16 downloaded from the CCDC.
;
_audit_creation_date             2024-01-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_chemical_formula_moiety         'C20 H13 I O3'
_chemical_formula_sum            'C20 H13 I O3'
_chemical_formula_weight         428.229
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
I -0.41187 1.83264 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07120 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   5.2435(1)
_cell_length_b                   16.7054(4)
_cell_length_c                   18.3220(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1604.91(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9927
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.94
_cell_measurement_theta_min      2.24
_exptl_absorpt_coefficient_mu    2.010
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.556
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.772
_exptl_crystal_description       needle-like
_exptl_crystal_F_000             838.895
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.28
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 1.0000
_diffrn_reflns_Laue_measured_fraction_max 0.9996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            82438
_diffrn_reflns_point_group_measured_fraction_full 0.9997
_diffrn_reflns_point_group_measured_fraction_max 0.9988
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         30.52
_diffrn_reflns_theta_min         1.65
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.998
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              23
_reflns_limit_k_min              -23
_reflns_limit_l_max              26
_reflns_limit_l_min              -25
_reflns_number_gt                4724
_reflns_number_total             4912
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.2895
_refine_diff_density_min         -0.4407
_refine_diff_density_rms         0.0686
_refine_ls_abs_structure_details 
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   0.000(6)
_refine_ls_d_res_high            0.6998
_refine_ls_d_res_low             12.3445
_refine_ls_goodness_of_fit_ref   1.0223
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    25
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4912
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0193
_refine_ls_R_factor_gt           0.0176
_refine_ls_restrained_S_all      1.0223
_refine_ls_shift/su_max          -0.0008
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0167P)²+0.7951P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0389
_refine_ls_wR_factor_ref         0.0395
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C10(H10), C11(H11), C13(H13), C14(H14), C19(H19),
 C20(H20)
2.c X=CH2 refined with riding coordinates:
 C18(H18a,H18b)
;
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_refinement_flags_posn
I1 I -0.02831(2) 0.332822(7) 0.546378(6) 0.01895(3) Uani 1.000000 .
O1 O 0.5615(2) 0.46996(7) 0.65186(7) 0.0155(2) Uani 1.000000 .
O2 O 0.0051(3) 0.68286(7) 0.68072(7) 0.0209(3) Uani 1.000000 .
O3 O 0.3115(3) 0.74281(8) 0.78873(9) 0.0262(3) Uani 1.000000 .
C1 C 0.2276(4) 0.67357(12) 0.40093(10) 0.0217(4) Uani 1.000000 .
H1 H 0.2341(4) 0.70426(12) 0.35862(10) 0.0260(4) Uiso 1.000000 R
C2 C 0.4117(3) 0.68315(10) 0.45452(11) 0.0212(3) Uani 1.000000 .
H2 H 0.5412(3) 0.72058(10) 0.44829(11) 0.0254(4) Uiso 1.000000 R
C3 C 0.4030(4) 0.63663(11) 0.51796(10) 0.0182(3) Uani 1.000000 .
H3 H 0.5280(4) 0.64287(11) 0.55352(10) 0.0218(4) Uiso 1.000000 R
C4 C 0.2085(3) 0.58107(10) 0.52817(9) 0.0145(3) Uani 1.000000 .
C5 C 0.1875(3) 0.53213(10) 0.59772(10) 0.0143(3) Uani 1.000000 .
H5 H 0.0086(3) 0.51763(10) 0.60569(10) 0.0172(4) Uiso 1.000000 R
C6 C 0.2875(3) 0.57409(10) 0.66450(10) 0.0144(3) Uani 1.000000 .
C7 C 0.4935(3) 0.53513(9) 0.69075(9) 0.0141(3) Uani 1.000000 .
C8 C 0.6394(3) 0.55571(10) 0.75548(10) 0.0144(3) Uani 1.000000 .
C9 C 0.5737(3) 0.62714(10) 0.79105(10) 0.0161(3) Uani 1.000000 .
C10 C 0.7110(4) 0.65118(10) 0.85208(10) 0.0178(4) Uani 1.000000 .
H10 H 0.6690(4) 0.69856(10) 0.87587(10) 0.0214(4) Uiso 1.000000 R
C11 C 0.9113(4) 0.60432(11) 0.87757(10) 0.0209(4) Uani 1.000000 .
H11 H 1.0048(4) 0.62108(11) 0.91790(10) 0.0251(5) Uiso 1.000000 R
C12 C 0.3548(3) 0.45443(10) 0.59985(10) 0.0153(3) Uani 1.000000 .
H12 H 0.4253(3) 0.44344(10) 0.55133(10) 0.0183(4) Uiso 1.000000 R
C13 C 0.9731(4) 0.53264(10) 0.84329(9) 0.0193(3) Uani 1.000000 .
H13 H 1.1044(4) 0.50093(10) 0.86136(9) 0.0231(4) Uiso 1.000000 R
C14 C 0.8370(4) 0.50849(11) 0.78164(10) 0.0168(3) Uani 1.000000 .
H14 H 0.8787(4) 0.46091(11) 0.75815(10) 0.0202(4) Uiso 1.000000 R
C15 C 0.3599(3) 0.67773(10) 0.76312(10) 0.0173(3) Uani 1.000000 .
C16 C 0.1960(4) 0.64587(10) 0.69893(10) 0.0160(4) Uani 1.000000 .
C17 C 0.2085(3) 0.38300(10) 0.62698(10) 0.0151(3) Uani 1.000000 .
C18 C 0.2139(4) 0.35290(11) 0.69359(10) 0.0173(4) Uani 1.000000 .
H18a H 0.1124(4) 0.30909(11) 0.70526(10) 0.0207(4) Uiso 1.000000 R
H18b H 0.3193(4) 0.37551(11) 0.72884(10) 0.0207(4) Uiso 1.000000 R
C19 C 0.0245(4) 0.57198(10) 0.47395(9) 0.0181(3) Uani 1.000000 .
H19 H -0.1058(4) 0.53481(10) 0.48007(9) 0.0217(4) Uiso 1.000000 R
C20 C 0.0339(4) 0.61812(11) 0.41057(10) 0.0216(4) Uani 1.000000 .
H20 H -0.0900(4) 0.61168(11) 0.37472(10) 0.0260(4) Uiso 1.000000 R


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 C17 2.1037(17) . ?
O1 C7 1.3491(19) . ?
O1 C12 1.466(2) . ?
O2 C16 1.223(2) . ?
O3 C15 1.211(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.386(3) . ?
C1 C20 1.386(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.399(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.392(2) . ?
C4 C5 1.518(2) . ?
C4 C19 1.393(2) . ?
C5 H5 0.9800 . ?
C5 C6 1.504(2) . ?
C5 C12 1.567(2) . ?
C6 C7 1.350(2) . ?
C6 C16 1.437(2) . ?
C7 C8 1.453(2) . ?
C8 C9 1.402(2) . ?
C8 C14 1.388(3) . ?
C9 C10 1.389(3) . ?
C9 C15 1.494(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.391(3) . ?
C11 H11 0.9300 . ?
C11 C13 1.390(3) . ?
C12 H12 0.9800 . ?
C12 C17 1.503(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.395(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.551(3) . ?
C17 C18 1.320(3) . ?
C18 H18a 0.9300 . ?
C18 H18b 0.9300 . ?
C19 H19 0.9300 . ?
C19 C20 1.395(2) . ?
C20 H20 0.9300 . ?

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
C12 O1 C7 106.88(13) . . ?
C2 C1 H1 120.09(11) . . ?
C20 C1 H1 120.09(11) . . ?
C20 C1 C2 119.83(17) . . ?
H2 C2 C1 119.95(11) . . ?
C3 C2 C1 120.11(16) . . ?
C3 C2 H2 119.95(10) . . ?
H3 C3 C2 119.80(10) . . ?
C4 C3 C2 120.40(17) . . ?
C4 C3 H3 119.80(11) . . ?
C5 C4 C3 121.68(16) . . ?
C19 C4 C3 118.97(16) . . ?
C19 C4 C5 119.32(15) . . ?
H5 C5 C4 109.12(9) . . ?
C6 C5 C4 113.99(14) . . ?
C6 C5 H5 109.12(9) . . ?
C12 C5 C4 115.24(14) . . ?
C12 C5 H5 109.12(9) . . ?
C12 C5 C6 99.83(14) . . ?
C7 C6 C5 110.12(15) . . ?
C16 C6 C5 129.01(17) . . ?
C16 C6 C7 120.86(17) . . ?
C6 C7 O1 114.37(15) . . ?
C8 C7 O1 118.88(15) . . ?
C8 C7 C6 126.75(15) . . ?
C9 C8 C7 116.84(16) . . ?
C14 C8 C7 122.73(16) . . ?
C14 C8 C9 120.42(17) . . ?
C10 C9 C8 119.53(17) . . ?
C15 C9 C8 120.41(16) . . ?
C15 C9 C10 120.05(16) . . ?
H10 C10 C9 120.04(11) . . ?
C11 C10 C9 119.92(17) . . ?
C11 C10 H10 120.04(11) . . ?
H11 C11 C10 119.70(11) . . ?
C13 C11 C10 120.60(18) . . ?
C13 C11 H11 119.70(11) . . ?
C5 C12 O1 106.47(13) . . ?
H12 C12 O1 110.10(9) . . ?
H12 C12 C5 110.10(9) . . ?
C17 C12 O1 107.62(14) . . ?
C17 C12 C5 112.34(14) . . ?
C17 C12 H12 110.10(10) . . ?
H13 C13 C11 120.15(11) . . ?
C14 C13 C11 119.71(18) . . ?
C14 C13 H13 120.15(11) . . ?
C13 C14 C8 119.80(17) . . ?
H14 C14 C8 120.10(11) . . ?
H14 C14 C13 120.10(11) . . ?
C9 C15 O3 122.16(17) . . ?
C16 C15 O3 119.07(17) . . ?
C16 C15 C9 118.77(15) . . ?
C6 C16 O2 125.10(18) . . ?
C15 C16 O2 119.15(16) . . ?
C15 C16 C6 115.74(17) . . ?
C12 C17 I1 112.67(12) . . ?
C18 C17 I1 120.65(14) . . ?
C18 C17 C12 126.66(16) . . ?
H18a C18 C17 120.0 . . ?
H18b C18 C17 120.0 . . ?
H18b C18 H18a 120.0 . . ?
H19 C19 C4 119.70(10) . . ?
C20 C19 C4 120.60(17) . . ?
C20 C19 H19 119.70(12) . . ?
C19 C20 C1 120.08(18) . . ?
H20 C20 C1 119.96(11) . . ?
H20 C20 C19 119.96(12) . . ?

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 C17 C12 O1 -164.23(11) . . . . ?
I1 C17 C12 C5 78.89(12) . . . . ?
O1 C7 C6 C5 0.55(16) . . . . ?
O1 C7 C6 C16 -178.32(14) . . . . ?
O1 C7 C8 C9 175.39(15) . . . . ?
O1 C7 C8 C14 -3.92(18) . . . . ?
O1 C12 C5 C4 108.54(14) . . . . ?
O1 C12 C5 C6 -14.00(14) . . . . ?
O1 C12 C17 C18 17.30(18) . . . . ?
O2 C16 C6 C5 4.7(2) . . . . ?
O2 C16 C6 C7 -176.67(18) . . . . ?
O2 C16 C15 O3 -7.9(2) . . . . ?
O2 C16 C15 C9 172.49(16) . . . . ?
O3 C15 C9 C8 -173.81(18) . . . . ?
O3 C15 C9 C10 5.4(2) . . . . ?
O3 C15 C16 C6 171.17(17) . . . . ?
C1 C2 C3 C4 -0.7(2) . . . . ?
C1 C20 C19 C4 0.1(2) . . . . ?
C2 C3 C4 C5 -177.45(16) . . . . ?
C2 C3 C4 C19 0.7(2) . . . . ?
C3 C4 C5 C6 30.45(19) . . . . ?
C3 C4 C5 C12 -84.15(18) . . . . ?
C3 C4 C19 C20 -0.4(2) . . . . ?
C4 C5 C6 C7 -114.88(16) . . . . ?
C4 C5 C6 C16 63.86(18) . . . . ?
C4 C5 C12 C17 -133.89(15) . . . . ?
C5 C6 C7 C8 -178.24(13) . . . . ?
C5 C6 C16 C15 -174.26(18) . . . . ?
C5 C12 C17 C18 -99.58(17) . . . . ?
C6 C7 C8 C9 -5.9(2) . . . . ?
C6 C7 C8 C14 174.82(18) . . . . ?
C6 C16 C15 C9 -8.48(18) . . . . ?
C7 C8 C9 C10 -178.21(15) . . . . ?
C7 C8 C9 C15 1.02(18) . . . . ?
C7 C8 C14 C13 178.63(17) . . . . ?
C8 C9 C10 C11 -0.2(2) . . . . ?
C8 C9 C15 C16 5.82(19) . . . . ?
C8 C14 C13 C11 -0.7(2) . . . . ?
C9 C10 C11 C13 -1.2(2) . . . . ?
C10 C11 C13 C14 1.6(2) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
