# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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 
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data_mo_jgocarka280421_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2232966'
loop_
_audit_author_name
_audit_author_address
'ARGHYADIP BHOWMIK'
;PhD Scholar at Indian Association for the Cultivation of Science
India
;
_audit_update_record             
;
2022-12-27 deposited with the CCDC.	2023-04-10 downloaded from the CCDC.
;
_audit_creation_date             2022-12-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '4(C18 H15 Br I N O4)'
_chemical_formula_sum            'C72 H60 Br4 I4 N4 O16'
_chemical_formula_weight         2064.48
_chemical_absolute_configuration Rmod
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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                   9.8468(4)
_cell_length_b                   10.3709(4)
_cell_length_c                   17.4196(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1778.89(13)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9953
_cell_measurement_temperature    134.31
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   0.686
_shelx_estimated_absorpt_T_min   0.235
_exptl_absorpt_coefficient_mu    4.069
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.2265
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1575 before and 0.0937 after correction.
The Ratio of minimum to maximum transmission is 0.3038.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.927
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0615
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20967
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.526
_diffrn_reflns_theta_min         2.285
_diffrn_ambient_temperature      134.31
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.752
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3965
_reflns_number_total             4089
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         1.098
_refine_diff_density_min         -0.653
_refine_diff_density_rms         0.098
_refine_ls_abs_structure_details 
;
 Flack x determined using 1637 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.117(6)
_refine_ls_extinction_coef       0.0051(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4089
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0270
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0236P)²+0.9398P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0638
_refine_ls_wR_factor_ref         0.0643
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C8(H8), C10(H10), C14(H14), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.10880(3) 0.37001(3) 0.14338(2) 0.02274(11) Uani 1 1 d . . . . .
Br1 Br 0.15740(6) 0.01282(5) 0.52620(3) 0.02595(14) Uani 1 1 d . . . . .
O1 O 0.3977(4) 1.0106(3) 0.32429(18) 0.0202(7) Uani 1 1 d . . . . .
O2 O 0.2914(3) 0.6259(3) 0.41115(18) 0.0179(6) Uani 1 1 d . . . . .
O3 O 0.5571(4) 0.7607(3) 0.23130(19) 0.0187(7) Uani 1 1 d . . . . .
H3 H 0.548406 0.693393 0.204904 0.028 Uiso 1 1 calc R U . . .
O4 O 0.1164(5) 0.6700(4) 0.4901(2) 0.0369(10) Uani 1 1 d . . . . .
N1 N 0.2349(4) 0.9338(4) 0.2415(2) 0.0161(8) Uani 1 1 d . . . . .
C2 C 0.0775(5) 0.6575(5) 0.1388(3) 0.0196(10) Uani 1 1 d . . . . .
H2 H 0.013986 0.636088 0.099806 0.023 Uiso 1 1 calc R U . . .
C3 C 0.1933(5) 0.5932(5) 0.4608(3) 0.0198(10) Uani 1 1 d . . . . .
C4 C 0.3551(5) 0.7773(4) 0.3119(2) 0.0132(9) Uani 1 1 d . . . . .
C1 C 0.3360(5) 0.9212(4) 0.2937(3) 0.0157(9) Uani 1 1 d . . . . .
C5 C 0.5050(4) 0.7387(5) 0.3065(3) 0.0153(9) Uani 1 1 d . . . . .
H5A H 0.558294 0.789303 0.344098 0.018 Uiso 1 1 calc R U . . .
H5B H 0.514721 0.646269 0.319623 0.018 Uiso 1 1 calc R U . . .
C6 C 0.1479(5) 0.5601(4) 0.1764(3) 0.0177(10) Uani 1 1 d . . . . .
C7 C 0.2608(4) 0.3649(5) 0.4299(3) 0.0192(9) Uani 1 1 d . . . . .
H7 H 0.315152 0.394580 0.388453 0.023 Uiso 1 1 calc R U . . .
C8 C 0.0993(5) 0.7870(5) 0.1580(3) 0.0189(9) Uani 1 1 d . . . . .
H8 H 0.050989 0.854705 0.133403 0.023 Uiso 1 1 calc R U . . .
C9 C 0.3015(5) 0.7616(4) 0.3941(3) 0.0169(9) Uani 1 1 d . . . . .
H9A H 0.364048 0.803772 0.430830 0.020 Uiso 1 1 calc R U . . .
H9B H 0.211106 0.802652 0.398910 0.020 Uiso 1 1 calc R U . . .
C10 C 0.2429(5) 0.5870(4) 0.2341(2) 0.0139(9) Uani 1 1 d . . . . .
H10 H 0.291621 0.519900 0.259049 0.017 Uiso 1 1 calc R U . . .
C11 C 0.1937(5) 0.8114(4) 0.2140(3) 0.0147(9) Uani 1 1 d . . . . .
C12 C 0.1902(5) 0.4518(5) 0.4752(3) 0.0156(9) Uani 1 1 d . . . . .
C13 C 0.2628(5) 0.7150(5) 0.2534(3) 0.0139(9) Uani 1 1 d . . . . .
C14 C 0.1041(5) 0.2774(5) 0.5532(3) 0.0193(9) Uani 1 1 d . . . . .
H14 H 0.051991 0.247150 0.595384 0.023 Uiso 1 1 calc R U . . .
C15 C 0.1780(5) 1.0548(4) 0.2167(3) 0.0208(10) Uani 1 1 d . . . . .
H15A H 0.212152 1.124386 0.249573 0.031 Uiso 1 1 calc R U . . .
H15B H 0.078780 1.051064 0.220407 0.031 Uiso 1 1 calc R U . . .
H15C H 0.204419 1.071394 0.163401 0.031 Uiso 1 1 calc R U . . .
C16 C 0.1739(5) 0.1925(5) 0.5072(3) 0.0180(9) Uani 1 1 d . . . . .
C17 C 0.2515(5) 0.2331(5) 0.4458(3) 0.0206(10) Uani 1 1 d . . . . .
H17 H 0.298018 0.172118 0.414778 0.025 Uiso 1 1 calc R U . . .
C18 C 0.1111(5) 0.4083(4) 0.5368(3) 0.0196(9) Uani 1 1 d . . . . .
H18 H 0.062343 0.468305 0.567442 0.024 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 C6 2.089(5) . ?
Br1 C16 1.900(5) . ?
O1 C1 1.230(6) . ?
O2 C3 1.340(6) . ?
O2 C9 1.441(6) . ?
O3 H3 0.8400 . ?
O3 C5 1.425(6) . ?
O4 C3 1.212(6) . ?
N1 C1 1.355(6) . ?
N1 C11 1.416(6) . ?
N1 C15 1.440(6) . ?
C2 H2 0.9500 . ?
C2 C6 1.389(7) . ?
C2 C8 1.401(7) . ?
C3 C12 1.488(7) . ?
C4 C1 1.538(6) . ?
C4 C5 1.532(6) . ?
C4 C9 1.536(6) . ?
C4 C13 1.510(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C10 1.401(6) . ?
C7 H7 0.9500 . ?
C7 C12 1.385(7) . ?
C7 C17 1.398(7) . ?
C8 H8 0.9500 . ?
C8 C11 1.371(7) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10 0.9500 . ?
C10 C13 1.384(7) . ?
C11 C13 1.391(6) . ?
C12 C18 1.401(7) . ?
C14 H14 0.9500 . ?
C14 C16 1.375(7) . ?
C14 C18 1.388(7) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.379(7) . ?
C17 H17 0.9500 . ?
C18 H18 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
C3 O2 C9 115.4(4) . . ?
C5 O3 H3 109.5 . . ?
C1 N1 C11 110.5(4) . . ?
C1 N1 C15 124.8(4) . . ?
C11 N1 C15 124.7(4) . . ?
C6 C2 H2 119.7 . . ?
C6 C2 C8 120.6(4) . . ?
C8 C2 H2 119.7 . . ?
O2 C3 C12 111.9(4) . . ?
O4 C3 O2 123.8(5) . . ?
O4 C3 C12 124.3(4) . . ?
C5 C4 C1 111.0(4) . . ?
C5 C4 C9 111.1(4) . . ?
C9 C4 C1 104.6(4) . . ?
C13 C4 C1 101.7(4) . . ?
C13 C4 C5 115.3(4) . . ?
C13 C4 C9 112.1(4) . . ?
O1 C1 N1 125.5(4) . . ?
O1 C1 C4 125.6(4) . . ?
N1 C1 C4 108.7(4) . . ?
O3 C5 C4 111.2(4) . . ?
O3 C5 H5A 109.4 . . ?
O3 C5 H5B 109.4 . . ?
C4 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C2 C6 I1 117.7(4) . . ?
C2 C6 C10 121.8(4) . . ?
C10 C6 I1 120.5(3) . . ?
C12 C7 H7 120.3 . . ?
C12 C7 C17 119.4(4) . . ?
C17 C7 H7 120.3 . . ?
C2 C8 H8 121.6 . . ?
C11 C8 C2 116.8(4) . . ?
C11 C8 H8 121.6 . . ?
O2 C9 C4 108.6(4) . . ?
O2 C9 H9A 110.0 . . ?
O2 C9 H9B 110.0 . . ?
C4 C9 H9A 110.0 . . ?
C4 C9 H9B 110.0 . . ?
H9A C9 H9B 108.4 . . ?
C6 C10 H10 121.3 . . ?
C13 C10 C6 117.4(4) . . ?
C13 C10 H10 121.3 . . ?
C8 C11 N1 126.9(4) . . ?
C8 C11 C13 123.4(4) . . ?
C13 C11 N1 109.7(4) . . ?
C7 C12 C3 122.3(4) . . ?
C7 C12 C18 120.4(4) . . ?
C18 C12 C3 117.3(4) . . ?
C10 C13 C4 131.3(4) . . ?
C10 C13 C11 120.1(4) . . ?
C11 C13 C4 108.6(4) . . ?
C16 C14 H14 120.6 . . ?
C16 C14 C18 118.8(4) . . ?
C18 C14 H14 120.6 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 Br1 119.0(4) . . ?
C14 C16 C17 122.2(5) . . ?
C17 C16 Br1 118.8(4) . . ?
C7 C17 H17 120.4 . . ?
C16 C17 C7 119.2(5) . . ?
C16 C17 H17 120.4 . . ?
C12 C18 H18 120.0 . . ?
C14 C18 C12 120.0(4) . . ?
C14 C18 H18 120.0 . . ?

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 C6 C10 C13 -179.5(3) . . . . ?
Br1 C16 C17 C7 178.0(4) . . . . ?
O2 C3 C12 C7 -12.8(7) . . . . ?
O2 C3 C12 C18 167.7(4) . . . . ?
O4 C3 C12 C7 167.0(5) . . . . ?
O4 C3 C12 C18 -12.5(8) . . . . ?
N1 C11 C13 C4 0.8(5) . . . . ?
N1 C11 C13 C10 -177.5(4) . . . . ?
C2 C6 C10 C13 0.9(7) . . . . ?
C2 C8 C11 N1 178.4(4) . . . . ?
C2 C8 C11 C13 -2.5(7) . . . . ?
C3 O2 C9 C4 -149.8(4) . . . . ?
C3 C12 C18 C14 180.0(5) . . . . ?
C1 N1 C11 C8 -176.4(5) . . . . ?
C1 N1 C11 C13 4.4(5) . . . . ?
C1 C4 C5 O3 -60.4(5) . . . . ?
C1 C4 C9 O2 169.4(4) . . . . ?
C1 C4 C13 C10 173.1(5) . . . . ?
C1 C4 C13 C11 -4.9(5) . . . . ?
C5 C4 C1 O1 -52.4(6) . . . . ?
C5 C4 C1 N1 130.7(4) . . . . ?
C5 C4 C9 O2 -70.8(5) . . . . ?
C5 C4 C13 C10 52.9(7) . . . . ?
C5 C4 C13 C11 -125.1(4) . . . . ?
C6 C2 C8 C11 0.9(7) . . . . ?
C6 C10 C13 C4 179.9(4) . . . . ?
C6 C10 C13 C11 -2.4(7) . . . . ?
C7 C12 C18 C14 0.5(8) . . . . ?
C8 C2 C6 I1 -179.8(4) . . . . ?
C8 C2 C6 C10 -0.2(7) . . . . ?
C8 C11 C13 C4 -178.5(4) . . . . ?
C8 C11 C13 C10 3.3(7) . . . . ?
C9 O2 C3 O4 0.3(7) . . . . ?
C9 O2 C3 C12 -179.9(4) . . . . ?
C9 C4 C1 O1 67.5(6) . . . . ?
C9 C4 C1 N1 -109.3(4) . . . . ?
C9 C4 C5 O3 -176.4(4) . . . . ?
C9 C4 C13 C10 -75.6(6) . . . . ?
C9 C4 C13 C11 106.4(4) . . . . ?
C11 N1 C1 O1 175.6(5) . . . . ?
C11 N1 C1 C4 -7.6(5) . . . . ?
C12 C7 C17 C16 -1.1(7) . . . . ?
C13 C4 C1 O1 -175.6(5) . . . . ?
C13 C4 C1 N1 7.6(5) . . . . ?
C13 C4 C5 O3 54.6(5) . . . . ?
C13 C4 C9 O2 59.9(5) . . . . ?
C14 C16 C17 C7 0.5(8) . . . . ?
C15 N1 C1 O1 -3.9(8) . . . . ?
C15 N1 C1 C4 172.9(4) . . . . ?
C15 N1 C11 C8 3.1(8) . . . . ?
C15 N1 C11 C13 -176.1(4) . . . . ?
C16 C14 C18 C12 -1.1(8) . . . . ?
C17 C7 C12 C3 -178.8(5) . . . . ?
C17 C7 C12 C18 0.6(7) . . . . ?
C18 C14 C16 Br1 -176.9(4) . . . . ?
C18 C14 C16 C17 0.6(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
