# Supplementary Information (SI) for Analytical Methods.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_cbk2
_database_code_depnum_ccdc_archive 'CCDC 2105055'
loop_
_audit_author_name
_audit_author_address
'Dr. C. Balakrishnan'
;Nazareth Margoschis College at Pillaiyanmanai
India
;
_audit_update_record             
;
2021-08-24 deposited with the CCDC.	2025-02-25 downloaded from the CCDC.
;
_audit_creation_date             2021-04-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C10 H9 Br2 N O)'
_chemical_formula_sum            'C20 H18 Br4 N2 O2'
_chemical_formula_weight         638.00
_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'
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      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/n 1'
_space_group_name_Hall           '-P 2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   15.9413(8)
_cell_length_b                   9.2450(5)
_cell_length_c                   16.0151(8)
_cell_angle_alpha                90
_cell_angle_beta                 110.540(2)
_cell_angle_gamma                90
_cell_volume                     2210.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9254
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      27.492
_cell_measurement_theta_min      2.588
_shelx_estimated_absorpt_T_max   0.707
_shelx_estimated_absorpt_T_min   0.292
_exptl_absorpt_coefficient_mu    7.302
_exptl_absorpt_correction_T_max  0.3334
_exptl_absorpt_correction_T_min  0.1454
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1062 before and 0.0588 after correction.
The Ratio of minimum to maximum transmission is 0.4361.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.917
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.224
_exptl_crystal_size_mid          0.062
_exptl_crystal_size_min          0.051
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            108971
_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         27.492
_diffrn_reflns_theta_min         2.203
_diffrn_ambient_temperature      110.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker QUEST PHOTON-III'
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4438
_reflns_number_total             5050
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.682
_refine_diff_density_min         -0.672
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         5050
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0246
_refine_ls_R_factor_gt           0.0187
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0173P)²+1.8308P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0415
_refine_ls_wR_factor_ref         0.0430
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C20(H20A,H20B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C4(H4), C7(H7), C17(H17), C16(H16), C14(H14)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_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
Br1 Br 0.40621(2) 0.28162(2) 0.61614(2) 0.02381(5) Uani 1 1 d . . . . .
Br2 Br 0.61294(2) 0.14593(3) 0.40491(2) 0.03578(6) Uani 1 1 d . . . . .
O1 O 0.54031(8) 0.52787(14) 0.67712(8) 0.0181(3) Uani 1 1 d . . . . .
H1 H 0.574389 0.600172 0.688762 0.027 Uiso 1 1 calc R U . . .
N1 N 0.67043(10) 0.69266(16) 0.67177(10) 0.0151(3) Uani 1 1 d . . . . .
C8 C 0.72783(11) 0.82017(19) 0.69908(11) 0.0154(4) Uani 1 1 d . . . . .
H8 H 0.775323 0.816128 0.671684 0.018 Uiso 1 1 calc R U . . .
C6 C 0.64523(12) 0.3864(2) 0.52290(12) 0.0170(4) Uani 1 1 d . . . . .
H6 H 0.692654 0.408262 0.501973 0.020 Uiso 1 1 calc R U . . .
C4 C 0.52201(12) 0.23350(19) 0.51990(11) 0.0164(4) Uani 1 1 d . . . . .
H4 H 0.485900 0.150547 0.497629 0.020 Uiso 1 1 calc R U . . .
C9 C 0.67178(13) 0.9569(2) 0.66735(13) 0.0226(4) Uani 1 1 d . . . . .
H9A H 0.646176 0.957219 0.601381 0.027 Uiso 1 1 calc R U . . .
H9B H 0.621486 0.956782 0.690082 0.027 Uiso 1 1 calc R U . . .
C10 C 0.72778(13) 1.0929(2) 0.69945(13) 0.0245(4) Uani 1 1 d . . . . .
H10A H 0.774366 1.098215 0.671838 0.029 Uiso 1 1 calc R U . . .
H10B H 0.688965 1.179237 0.680547 0.029 Uiso 1 1 calc R U . . .
C7 C 0.68562(11) 0.60304(19) 0.61820(11) 0.0148(3) Uani 1 1 d . . . . .
H7 H 0.734535 0.619659 0.598563 0.018 Uiso 1 1 calc R U . . .
C3 C 0.50559(12) 0.3226(2) 0.58185(11) 0.0155(3) Uani 1 1 d . . . . .
C1 C 0.62930(11) 0.47506(19) 0.58629(11) 0.0131(3) Uani 1 1 d . . . . .
C2 C 0.55835(11) 0.44421(19) 0.61709(11) 0.0136(3) Uani 1 1 d . . . . .
C5 C 0.59197(12) 0.2671(2) 0.49083(12) 0.0182(4) Uani 1 1 d . . . . .
Br3 Br 0.88805(2) 0.31098(2) 0.61888(2) 0.02212(5) Uani 1 1 d . . . . .
Br4 Br 1.06191(2) 0.12130(2) 0.38603(2) 0.02321(5) Uani 1 1 d . . . . .
O2 O 0.82111(8) 0.54612(14) 0.47902(8) 0.0167(3) Uani 1 1 d . . . . .
H2 H 0.806588 0.613882 0.441735 0.025 Uiso 1 1 calc R U . . .
N2 N 0.81656(9) 0.69680(16) 0.33982(9) 0.0131(3) Uani 1 1 d . . . . .
C11 C 0.89925(11) 0.47499(19) 0.38155(11) 0.0128(3) Uani 1 1 d . . . . .
C15 C 0.98826(11) 0.25899(19) 0.41529(12) 0.0151(3) Uani 1 1 d . . . . .
C17 C 0.87003(11) 0.60387(19) 0.32633(11) 0.0137(3) Uani 1 1 d . . . . .
H17 H 0.891436 0.619406 0.278664 0.016 Uiso 1 1 calc R U . . .
C13 C 0.91139(11) 0.3349(2) 0.51179(11) 0.0146(3) Uani 1 1 d . . . . .
C16 C 0.95626(11) 0.37757(19) 0.36108(11) 0.0147(3) Uani 1 1 d . . . . .
H16 H 0.972847 0.392837 0.310285 0.018 Uiso 1 1 calc R U . . .
C18 C 0.79783(11) 0.82728(18) 0.28400(11) 0.0121(3) Uani 1 1 d . . . . .
H18 H 0.840936 0.831910 0.251335 0.015 Uiso 1 1 calc R U . . .
C20 C 0.79523(11) 1.09947(19) 0.28781(11) 0.0156(4) Uani 1 1 d . . . . .
H20A H 0.798538 1.183720 0.326993 0.019 Uiso 1 1 calc R U . . .
H20B H 0.843405 1.109707 0.262556 0.019 Uiso 1 1 calc R U . . .
C12 C 0.87531(11) 0.45394(19) 0.45758(11) 0.0126(3) Uani 1 1 d . . . . .
C14 C 0.96677(11) 0.23676(19) 0.49099(12) 0.0153(3) Uani 1 1 d . . . . .
H14 H 0.989716 0.155279 0.528144 0.018 Uiso 1 1 calc R U . . .
C19 C 0.81049(11) 0.96132(19) 0.34309(11) 0.0145(3) Uani 1 1 d . . . . .
H19A H 0.767824 0.957871 0.375478 0.017 Uiso 1 1 calc R U . . .
H19B H 0.871961 0.961714 0.387760 0.017 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
Br1 C3 1.8882(18) . ?
Br2 C5 1.8929(18) . ?
O1 H1 0.8400 . ?
O1 C2 1.341(2) . ?
N1 C8 1.462(2) . ?
N1 C7 1.276(2) . ?
C8 C8 1.533(3) 2_656 ?
C8 H8 1.0000 . ?
C8 C9 1.528(3) . ?
C6 H6 0.9500 . ?
C6 C1 1.396(2) . ?
C6 C5 1.376(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.384(3) . ?
C4 C5 1.386(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.523(3) . ?
C10 C10 1.523(4) 2_656 ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C7 H7 0.9500 . ?
C7 C1 1.465(2) . ?
C3 C2 1.399(2) . ?
C1 C2 1.413(2) . ?
Br3 C13 1.8911(17) . ?
Br4 C15 1.8985(17) . ?
O2 H2 0.8400 . ?
O2 C12 1.341(2) . ?
N2 C17 1.281(2) . ?
N2 C18 1.468(2) . ?
C11 C17 1.459(2) . ?
C11 C16 1.398(2) . ?
C11 C12 1.412(2) . ?
C15 C16 1.380(2) . ?
C15 C14 1.386(3) . ?
C17 H17 0.9500 . ?
C13 C12 1.394(2) . ?
C13 C14 1.386(3) . ?
C16 H16 0.9500 . ?
C18 C18 1.532(3) 2_655 ?
C18 H18 1.0000 . ?
C18 C19 1.529(2) . ?
C20 C20 1.523(3) 2_655 ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C19 1.524(2) . ?
C14 H14 0.9500 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?

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
C2 O1 H1 109.5 . . ?
C7 N1 C8 118.58(15) . . ?
N1 C8 C8 108.95(12) . 2_656 ?
N1 C8 H8 109.2 . . ?
N1 C8 C9 109.62(14) . . ?
C8 C8 H8 109.2 2_656 . ?
C9 C8 C8 110.56(13) . 2_656 ?
C9 C8 H8 109.2 . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C5 C6 C1 119.74(17) . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 118.96(16) . . ?
C5 C4 H4 120.5 . . ?
C8 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 C8 111.43(15) . . ?
C10 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
C10 C10 C9 110.97(14) 2_656 . ?
C10 C10 H10A 109.4 2_656 . ?
C10 C10 H10B 109.4 2_656 . ?
H10A C10 H10B 108.0 . . ?
N1 C7 H7 119.3 . . ?
N1 C7 C1 121.44(16) . . ?
C1 C7 H7 119.3 . . ?
C4 C3 Br1 118.56(13) . . ?
C4 C3 C2 121.99(16) . . ?
C2 C3 Br1 119.42(13) . . ?
C6 C1 C7 118.85(16) . . ?
C6 C1 C2 120.51(16) . . ?
C2 C1 C7 120.61(16) . . ?
O1 C2 C3 120.19(16) . . ?
O1 C2 C1 122.22(15) . . ?
C3 C2 C1 117.59(16) . . ?
C6 C5 Br2 120.15(14) . . ?
C6 C5 C4 121.20(17) . . ?
C4 C5 Br2 118.65(14) . . ?
C12 O2 H2 109.5 . . ?
C17 N2 C18 116.96(14) . . ?
C16 C11 C17 118.66(16) . . ?
C16 C11 C12 120.55(16) . . ?
C12 C11 C17 120.66(15) . . ?
C16 C15 Br4 120.09(14) . . ?
C16 C15 C14 121.19(16) . . ?
C14 C15 Br4 118.72(13) . . ?
N2 C17 C11 122.36(16) . . ?
N2 C17 H17 118.8 . . ?
C11 C17 H17 118.8 . . ?
C12 C13 Br3 119.19(13) . . ?
C14 C13 Br3 119.07(13) . . ?
C14 C13 C12 121.69(16) . . ?
C11 C16 H16 120.3 . . ?
C15 C16 C11 119.44(16) . . ?
C15 C16 H16 120.3 . . ?
N2 C18 C18 111.83(11) . 2_655 ?
N2 C18 H18 108.9 . . ?
N2 C18 C19 109.54(13) . . ?
C18 C18 H18 108.9 2_655 . ?
C19 C18 C18 108.80(12) . 2_655 ?
C19 C18 H18 108.9 . . ?
C20 C20 H20A 109.2 2_655 . ?
C20 C20 H20B 109.2 2_655 . ?
C20 C20 C19 112.05(11) 2_655 . ?
H20A C20 H20B 107.9 . . ?
C19 C20 H20A 109.2 . . ?
C19 C20 H20B 109.2 . . ?
O2 C12 C11 121.78(15) . . ?
O2 C12 C13 120.25(15) . . ?
C13 C12 C11 117.95(16) . . ?
C15 C14 C13 119.14(16) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C18 C19 H19A 109.4 . . ?
C18 C19 H19B 109.4 . . ?
C20 C19 C18 111.10(14) . . ?
C20 C19 H19A 109.4 . . ?
C20 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?

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
Br1 C3 C2 O1 2.4(2) . . . . ?
Br1 C3 C2 C1 -176.88(12) . . . . ?
N1 C8 C9 C10 176.38(16) . . . . ?
N1 C7 C1 C6 175.51(16) . . . . ?
N1 C7 C1 C2 -2.6(3) . . . . ?
C8 N1 C7 C1 -178.38(15) . . . . ?
C8 C8 C9 C10 56.2(2) 2_656 . . . ?
C8 C9 C10 C10 -56.2(3) . . . 2_656 ?
C6 C1 C2 O1 -179.18(16) . . . . ?
C6 C1 C2 C3 0.1(2) . . . . ?
C4 C3 C2 O1 -179.92(16) . . . . ?
C4 C3 C2 C1 0.8(3) . . . . ?
C7 N1 C8 C8 -121.56(18) . . . 2_656 ?
C7 N1 C8 C9 117.33(18) . . . . ?
C7 C1 C2 O1 -1.1(2) . . . . ?
C7 C1 C2 C3 178.13(15) . . . . ?
C3 C4 C5 Br2 -179.19(13) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C1 C6 C5 Br2 -179.95(13) . . . . ?
C1 C6 C5 C4 0.4(3) . . . . ?
C5 C6 C1 C7 -178.78(16) . . . . ?
C5 C6 C1 C2 -0.7(3) . . . . ?
C5 C4 C3 Br1 176.65(13) . . . . ?
C5 C4 C3 C2 -1.1(3) . . . . ?
Br3 C13 C12 O2 -3.3(2) . . . . ?
Br3 C13 C12 C11 175.36(12) . . . . ?
Br3 C13 C14 C15 -176.18(13) . . . . ?
Br4 C15 C16 C11 177.50(12) . . . . ?
Br4 C15 C14 C13 -178.55(13) . . . . ?
N2 C18 C19 C20 177.75(14) . . . . ?
C17 N2 C18 C18 108.82(19) . . . 2_655 ?
C17 N2 C18 C19 -130.47(16) . . . . ?
C17 C11 C16 C15 176.68(15) . . . . ?
C17 C11 C12 O2 3.9(2) . . . . ?
C17 C11 C12 C13 -174.74(15) . . . . ?
C16 C11 C17 N2 178.70(16) . . . . ?
C16 C11 C12 O2 179.66(15) . . . . ?
C16 C11 C12 C13 1.0(2) . . . . ?
C16 C15 C14 C13 0.7(3) . . . . ?
C18 N2 C17 C11 175.40(14) . . . . ?
C18 C18 C19 C20 -59.7(2) 2_655 . . . ?
C20 C20 C19 C18 53.9(2) 2_655 . . . ?
C12 C11 C17 N2 -5.5(2) . . . . ?
C12 C11 C16 C15 0.8(2) . . . . ?
C12 C13 C14 C15 1.3(3) . . . . ?
C14 C15 C16 C11 -1.7(3) . . . . ?
C14 C13 C12 O2 179.24(15) . . . . ?
C14 C13 C12 C11 -2.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dimethylformamide'
