# Supplementary Information (SI) for Catalysis Science & Technology.
# 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 
# this file and to allow appropriate attribution of the data. 
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data_hdj_56_5_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2441463'
loop_
_audit_author_name
_audit_author_address
'Srinu Tothadi'
;CSIR CSMCRI
India
;
_audit_update_record             
;
2025-04-07 deposited with the CCDC.	2025-11-25 downloaded from the CCDC.
;
_audit_creation_date             2025-01-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H8 Br2 O4'
_chemical_formula_sum            'C10 H8 Br2 O4'
_chemical_formula_weight         351.98
_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'
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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.3464(5)
_cell_length_b                   6.2562(2)
_cell_length_c                   15.9702(6)
_cell_angle_alpha                90
_cell_angle_beta                 110.806(2)
_cell_angle_gamma                90
_cell_volume                     1153.12(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9961
_cell_measurement_temperature    298
_cell_measurement_theta_max      30.108
_cell_measurement_theta_min      2.586
_shelx_estimated_absorpt_T_max   0.817
_shelx_estimated_absorpt_T_min   0.365
_exptl_absorpt_coefficient_mu    7.024
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5397
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1097 before and 0.0778 after correction. The Ratio of minimum to maximum transmission is 0.7234. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.027
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0942
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            60533
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.622
_diffrn_reflns_theta_min         2.586
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2344
_reflns_number_total             3540
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.690
_refine_diff_density_min         -0.702
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         3540
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0389
_refine_ls_restrained_S_all      1.017
_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)+(0.0174P)²+1.5512P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0714
_refine_ls_wR_factor_ref         0.0843
_refine_special_details          ?
_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:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C8(H8), C9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.74228(4) 0.41292(8) 0.46498(3) 0.07277(15) Uani 1 1 d . . . . .
Br2 Br 0.44624(3) 0.11065(5) 0.63777(2) 0.05662(12) Uani 1 1 d . . . . .
O1 O 0.52729(19) 0.5004(4) 0.74734(14) 0.0504(5) Uani 1 1 d . . . . .
O2 O 0.5265(2) 0.3891(4) 0.91148(15) 0.0557(6) Uani 1 1 d . . . . .
O3 O 0.4387(4) 0.0737(4) 0.8722(2) 0.1003(12) Uani 1 1 d . . . . .
O4 O 0.3444(2) 0.3767(4) 0.82250(19) 0.0679(7) Uani 1 1 d . . . . .
C1 C 0.6771(3) 0.4459(6) 0.5558(2) 0.0512(8) Uani 1 1 d . . . . .
C2 C 0.5989(3) 0.2957(5) 0.56196(19) 0.0472(7) Uani 1 1 d . . . . .
H2 H 0.578154 0.180956 0.522427 0.057 Uiso 1 1 calc R . . . .
C3 C 0.5520(3) 0.3185(5) 0.62762(19) 0.0410(6) Uani 1 1 d . . . . .
C4 C 0.5808(3) 0.4906(5) 0.68649(19) 0.0414(6) Uani 1 1 d . . . . .
C5 C 0.5664(3) 0.6518(5) 0.8182(2) 0.0469(7) Uani 1 1 d . . . . .
H5A H 0.550848 0.796286 0.795004 0.056 Uiso 1 1 calc R . . . .
H5B H 0.649010 0.636683 0.850300 0.056 Uiso 1 1 calc R . . . .
C6 C 0.5003(3) 0.6046(4) 0.8789(2) 0.0439(7) Uani 1 1 d . . . . .
H6 H 0.522863 0.705084 0.929302 0.053 Uiso 1 1 calc R . . . .
C7 C 0.4367(4) 0.2635(6) 0.8685(3) 0.0621(10) Uani 1 1 d . . . . .
C8 C 0.7090(3) 0.6143(6) 0.6134(2) 0.0576(9) Uani 1 1 d . . . . .
H8 H 0.762982 0.712774 0.608760 0.069 Uiso 1 1 calc R . . . .
C9 C 0.6605(3) 0.6384(5) 0.6789(2) 0.0537(8) Uani 1 1 d . . . . .
H9 H 0.681475 0.754138 0.717926 0.064 Uiso 1 1 calc R . . . .
C10 C 0.3704(3) 0.6012(6) 0.8344(3) 0.0596(9) Uani 1 1 d . . . . .
H10A H 0.333175 0.666599 0.872184 0.072 Uiso 1 1 calc R . . . .
H10B H 0.346046 0.675050 0.777261 0.072 Uiso 1 1 calc R . . . .


_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 C1 1.903(3) . ?
Br2 C3 1.890(3) . ?
O1 C4 1.356(3) . ?
O1 C5 1.423(3) . ?
O2 C6 1.440(3) . ?
O2 C7 1.332(5) . ?
O3 C7 1.189(4) . ?
O4 C7 1.321(5) . ?
O4 C10 1.439(4) . ?
C1 C2 1.376(5) . ?
C1 C8 1.362(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.374(4) . ?
C3 C4 1.390(4) . ?
C4 C9 1.387(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.502(4) . ?
C6 H6 0.9800 . ?
C6 C10 1.505(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.386(5) . ?
C9 H9 0.9300 . ?
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
C4 O1 C5 119.1(2) . . ?
C7 O2 C6 109.1(3) . . ?
C7 O4 C10 110.0(3) . . ?
C2 C1 Br1 118.6(3) . . ?
C8 C1 Br1 120.0(3) . . ?
C8 C1 C2 121.4(3) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.8(3) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 Br2 119.0(2) . . ?
C2 C3 C4 121.4(3) . . ?
C4 C3 Br2 119.6(2) . . ?
O1 C4 C3 116.6(3) . . ?
O1 C4 C9 125.0(3) . . ?
C9 C4 C3 118.4(3) . . ?
O1 C5 H5A 110.6 . . ?
O1 C5 H5B 110.6 . . ?
O1 C5 C6 105.9(2) . . ?
H5A C5 H5B 108.7 . . ?
C6 C5 H5A 110.6 . . ?
C6 C5 H5B 110.6 . . ?
O2 C6 C5 108.2(2) . . ?
O2 C6 H6 110.0 . . ?
O2 C6 C10 102.8(3) . . ?
C5 C6 H6 110.0 . . ?
C5 C6 C10 115.4(3) . . ?
C10 C6 H6 110.0 . . ?
O3 C7 O2 124.4(5) . . ?
O3 C7 O4 124.1(4) . . ?
O4 C7 O2 111.4(3) . . ?
C1 C8 H8 120.1 . . ?
C1 C8 C9 119.7(3) . . ?
C9 C8 H8 120.1 . . ?
C4 C9 H9 119.9 . . ?
C8 C9 C4 120.2(3) . . ?
C8 C9 H9 119.9 . . ?
O4 C10 C6 103.1(3) . . ?
O4 C10 H10A 111.1 . . ?
O4 C10 H10B 111.1 . . ?
C6 C10 H10A 111.1 . . ?
C6 C10 H10B 111.1 . . ?
H10A C10 H10B 109.1 . . ?

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
Br1 C1 C2 C3 179.8(2) . . . . ?
Br1 C1 C8 C9 179.5(3) . . . . ?
Br2 C3 C4 O1 -1.6(4) . . . . ?
Br2 C3 C4 C9 178.6(2) . . . . ?
O1 C4 C9 C8 -179.2(3) . . . . ?
O1 C5 C6 O2 60.3(3) . . . . ?
O1 C5 C6 C10 -54.3(3) . . . . ?
O2 C6 C10 O4 -17.4(3) . . . . ?
C1 C2 C3 Br2 -179.0(2) . . . . ?
C1 C2 C3 C4 0.9(5) . . . . ?
C1 C8 C9 C4 0.7(5) . . . . ?
C2 C1 C8 C9 -1.1(5) . . . . ?
C2 C3 C4 O1 178.4(3) . . . . ?
C2 C3 C4 C9 -1.3(5) . . . . ?
C3 C4 C9 C8 0.5(5) . . . . ?
C4 O1 C5 C6 -173.4(3) . . . . ?
C5 O1 C4 C3 170.0(3) . . . . ?
C5 O1 C4 C9 -10.3(5) . . . . ?
C5 C6 C10 O4 100.3(3) . . . . ?
C6 O2 C7 O3 169.3(3) . . . . ?
C6 O2 C7 O4 -11.7(4) . . . . ?
C7 O2 C6 C5 -104.5(3) . . . . ?
C7 O2 C6 C10 18.1(3) . . . . ?
C7 O4 C10 C6 11.7(4) . . . . ?
C8 C1 C2 C3 0.3(5) . . . . ?
C10 O4 C7 O2 -0.6(4) . . . . ?
C10 O4 C7 O3 178.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
