# Supplementary Information (SI) for ChemComm.
# 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. 
# 
#######################################################################

data_20230321-2
_audit_block_doi                 10.5517/ccdc.csd.cc2g1d86
_database_code_depnum_ccdc_archive 'CCDC 2265457'
loop_
_audit_author_name
_audit_author_address
'hou ming'
;China
China
;
_audit_update_record             
;
2023-05-25 deposited with the CCDC.	2024-12-16 downloaded from the CCDC.
;
_audit_creation_date             2023-03-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C10 H9 Br O3)'
_chemical_formula_sum            'C20 H18 Br2 O6'
_chemical_formula_weight         514.16
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Br'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0181 0.0091 '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'
H H 0.0000 0.0000 '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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   10.7195(4)
_cell_length_b                   14.0637(5)
_cell_length_c                   13.2599(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1999.01(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1574
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.9270
_cell_measurement_theta_min      5.1650
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.449
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34014
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.708
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4346
_diffrn_reflns_point_group_measured_fraction_full 0.615
_diffrn_reflns_point_group_measured_fraction_max 0.594
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.153
_diffrn_reflns_theta_min         5.188
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0802
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     47.00  74.00   1.00    1.11    --   36.58 -99.00   0.00   27
  2  ω     -3.00  26.00   1.00    1.11    --   36.58 -99.00   0.00   29
  3  ω     60.00 108.00   1.00    1.11    --   36.58 178.00 -30.00   48
  4  ω     59.00  94.00   1.00    1.11    --   36.58 178.00-180.00   35
  5  ω     69.00  95.00   1.00    1.11    --   36.58  77.00 -60.00   26
  6  ω     58.00  94.00   1.00    1.11    --   36.58 178.00 120.00   36
  7  ω     33.00  66.00   1.00    1.11    --   36.58 -99.00-150.00   33
  8  ω     97.00 173.00   1.00    4.43    --  108.00  61.00 -30.00   76
  9  ω    100.00 164.00   1.00    4.43    --  108.00 111.00-150.00   64
 10  ω     60.00 117.00   1.00    4.43    --  108.00 -45.00  60.00   57
 11  ω    101.00 176.00   1.00    4.43    --  108.00 111.00   0.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1057042000
_diffrn_orient_matrix_UB_12      -0.0240160000
_diffrn_orient_matrix_UB_13      -0.0233744000
_diffrn_orient_matrix_UB_21      0.0005958000
_diffrn_orient_matrix_UB_22      -0.1122083000
_diffrn_orient_matrix_UB_23      0.0726348000
_diffrn_orient_matrix_UB_31      -0.0286993000
_diffrn_orient_matrix_UB_32      0.0864758000
_diffrn_orient_matrix_UB_33      0.0876583000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.170
_reflns_Friedel_fraction_full    0.191
_reflns_Friedel_fraction_max     0.182
_reflns_number_gt                1941
_reflns_number_total             2352
_reflns_odcompleteness_completeness 99.81
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.636
_refine_diff_density_min         -0.776
_refine_diff_density_rms         0.152
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.06(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.227
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         2352
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0593
_refine_ls_restrained_S_all      1.226
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1702
_refine_ls_wR_factor_ref         0.1810
_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:
 C00R(H00N,H00O), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00B(H00B), C00D(H00F), C00H(H00H), C00I(H00I), C00L(H00L),
 C00M(H00M), C00P(H00P)
2.c Idealised Me refined as rotating group:
 C00N(H00C,H00D,H00E), C00Q(H00G,H00J,H00K)
;
_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
Br01 Br 0.57404(10) 0.33726(6) 0.62576(12) 0.0617(4) Uani 1 1 d . . . . .
Br02 Br 0.69917(11) 1.16159(6) 0.37132(11) 0.0675(4) Uani 1 1 d . . . . .
O003 O 0.7264(4) 0.5160(4) 0.6222(9) 0.0608(18) Uani 1 1 d . . . . .
O004 O 0.6908(5) 0.5090(4) 0.3659(9) 0.0463(16) Uani 1 1 d . . . . .
O005 O 0.3736(5) 0.9616(4) 0.6172(9) 0.0602(18) Uani 1 1 d . . . . .
O10 O 0.5770(5) 0.9906(4) 0.6320(11) 0.0509(19) Uani 1 1 d . . . . .
O007 O 0.8966(5) 0.5374(4) 0.3783(9) 0.0592(17) Uani 1 1 d . . . . .
C008 C 0.5785(6) 0.6409(5) 0.6236(10) 0.0300(13) Uani 1 1 d . . . . .
O009 O 0.5445(5) 0.9848(5) 0.3812(10) 0.068(2) Uani 1 1 d . . . . .
C00A C 0.6726(6) 0.7094(5) 0.6279(8) 0.0347(15) Uani 1 1 d . . . . .
H00A H 0.755765 0.690772 0.630349 0.042 Uiso 1 1 calc R . . . .
C00B C 0.6425(6) 0.8042(5) 0.6286(8) 0.0329(14) Uani 1 1 d . . . . .
H00B H 0.705078 0.849962 0.631574 0.039 Uiso 1 1 calc R . . . .
C00C C 0.6183(6) 0.5372(4) 0.6234(8) 0.0312(13) Uani 1 1 d . . . . .
C00D C 0.8163(7) 0.8302(5) 0.3875(7) 0.0347(19) Uani 1 1 d . . . . .
H00F H 0.878884 0.875681 0.393300 0.042 Uiso 1 1 calc R . . . .
C00E C 0.6524(6) 0.9620(5) 0.3786(8) 0.0335(15) Uani 1 1 d . . . . .
C00F C 0.7525(9) 0.6675(4) 0.3777(9) 0.0316(13) Uani 1 1 d . . . . .
C00G C 0.5176(6) 0.8316(4) 0.6248(9) 0.0323(14) Uani 1 1 d . . . . .
C00H C 0.5977(6) 0.7903(5) 0.3709(8) 0.0365(15) Uani 1 1 d . . . . .
H00H H 0.514616 0.809028 0.366882 0.044 Uiso 1 1 calc R . . . .
C00I C 0.4251(5) 0.7631(5) 0.6173(9) 0.0414(17) Uani 1 1 d . . . . .
H00I H 0.342082 0.781574 0.612273 0.050 Uiso 1 1 calc R . . . .
C00J C 0.7898(7) 0.5640(5) 0.3756(8) 0.0383(16) Uani 1 1 d . . . . .
C00K C 0.6907(7) 0.8575(5) 0.3785(8) 0.0286(14) Uani 1 1 d . . . . .
C00L C 0.6282(6) 0.6957(5) 0.3694(7) 0.0338(15) Uani 1 1 d . . . . .
H00L H 0.565873 0.650121 0.362813 0.041 Uiso 1 1 calc R . . . .
C00M C 0.8445(6) 0.7353(6) 0.3877(7) 0.0397(18) Uani 1 1 d . . . . .
H00M H 0.927124 0.716253 0.394541 0.048 Uiso 1 1 calc R . . . .
C00N C 0.5516(9) 1.0918(5) 0.6322(13) 0.056(2) Uani 1 1 d . . . . .
H00C H 0.528981 1.111805 0.565433 0.083 Uiso 1 1 calc GR . . . .
H00D H 0.624874 1.125591 0.653490 0.083 Uiso 1 1 calc GR . . . .
H00E H 0.484297 1.105101 0.677781 0.083 Uiso 1 1 calc GR . . . .
C00O C 0.4802(7) 0.9347(5) 0.6232(9) 0.0376(15) Uani 1 1 d . . . . .
C00P C 0.4553(7) 0.6668(5) 0.6173(9) 0.0367(17) Uani 1 1 d . . . . .
H00P H 0.393140 0.620896 0.613054 0.044 Uiso 1 1 calc R . . . .
C00Q C 0.7153(9) 0.4082(6) 0.3655(15) 0.061(3) Uani 1 1 d . . . . .
H00G H 0.769158 0.392841 0.309941 0.091 Uiso 1 1 calc GR . . . .
H00J H 0.638132 0.374127 0.358560 0.091 Uiso 1 1 calc GR . . . .
H00K H 0.754937 0.390389 0.427579 0.091 Uiso 1 1 calc GR . . . .
C00R C 0.7557(9) 1.0340(5) 0.3772(14) 0.054(2) Uani 1 1 d . . . . .
H00N H 0.808573 1.021785 0.319254 0.065 Uiso 1 1 calc R . . . .
H00O H 0.806131 1.025959 0.437272 0.065 Uiso 1 1 calc R . . . .
C9 C 0.5155(6) 0.4653(5) 0.6255(12) 0.047(2) Uani 1 1 d . . . . .
H9A H 0.462402 0.474740 0.567118 0.057 Uiso 1 1 calc R . . . .
H9B H 0.465030 0.475634 0.685261 0.057 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
Br01 C9 1.907(7) . ?
Br02 C00R 1.895(7) . ?
O003 C00C 1.196(8) . ?
O004 C00J 1.320(9) . ?
O004 C00Q 1.442(9) . ?
O005 C00O 1.206(9) . ?
O10 C00N 1.449(9) . ?
O10 C00O 1.307(8) . ?
O007 C00J 1.205(9) . ?
C008 C00A 1.396(8) . ?
C008 C00C 1.519(9) . ?
C008 C00P 1.372(10) . ?
O009 C00E 1.201(8) . ?
C00A H00A 0.9300 . ?
C00A C00B 1.372(10) . ?
C00B H00B 0.9300 . ?
C00B C00G 1.394(9) . ?
C00C C9 1.497(9) . ?
C00D H00F 0.9300 . ?
C00D C00K 1.405(9) . ?
C00D C00M 1.369(11) . ?
C00E C00K 1.526(9) . ?
C00E C00R 1.500(10) . ?
C00F C00J 1.510(8) . ?
C00F C00L 1.394(11) . ?
C00F C00M 1.378(11) . ?
C00G C00I 1.386(9) . ?
C00G C00O 1.505(8) . ?
C00H H00H 0.9300 . ?
C00H C00K 1.378(10) . ?
C00H C00L 1.371(10) . ?
C00I H00I 0.9300 . ?
C00I C00P 1.392(10) . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00N H00C 0.9600 . ?
C00N H00D 0.9600 . ?
C00N H00E 0.9600 . ?
C00P H00P 0.9300 . ?
C00Q H00G 0.9600 . ?
C00Q H00J 0.9600 . ?
C00Q H00K 0.9600 . ?
C00R H00N 0.9700 . ?
C00R H00O 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 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
C00J O004 C00Q 115.5(7) . . ?
C00O O10 C00N 116.2(6) . . ?
C00A C008 C00C 117.4(5) . . ?
C00P C008 C00A 120.9(6) . . ?
C00P C008 C00C 121.7(6) . . ?
C008 C00A H00A 119.9 . . ?
C00B C00A C008 120.1(6) . . ?
C00B C00A H00A 119.9 . . ?
C00A C00B H00B 120.2 . . ?
C00A C00B C00G 119.6(6) . . ?
C00G C00B H00B 120.2 . . ?
O003 C00C C008 120.8(6) . . ?
O003 C00C C9 123.0(6) . . ?
C9 C00C C008 116.2(6) . . ?
C00K C00D H00F 120.7 . . ?
C00M C00D H00F 120.7 . . ?
C00M C00D C00K 118.6(7) . . ?
O009 C00E C00K 121.1(6) . . ?
O009 C00E C00R 122.1(7) . . ?
C00R C00E C00K 116.9(6) . . ?
C00L C00F C00J 121.7(7) . . ?
C00M C00F C00J 118.7(8) . . ?
C00M C00F C00L 119.6(6) . . ?
C00B C00G C00O 121.5(6) . . ?
C00I C00G C00B 119.9(6) . . ?
C00I C00G C00O 118.6(6) . . ?
C00K C00H H00H 120.2 . . ?
C00L C00H H00H 120.2 . . ?
C00L C00H C00K 119.6(6) . . ?
C00G C00I H00I 119.7 . . ?
C00G C00I C00P 120.6(6) . . ?
C00P C00I H00I 119.7 . . ?
O004 C00J C00F 110.7(6) . . ?
O007 C00J O004 125.8(7) . . ?
O007 C00J C00F 123.4(7) . . ?
C00D C00K C00E 121.4(6) . . ?
C00H C00K C00D 120.8(7) . . ?
C00H C00K C00E 117.8(7) . . ?
C00F C00L H00L 119.9 . . ?
C00H C00L C00F 120.2(6) . . ?
C00H C00L H00L 119.9 . . ?
C00D C00M C00F 121.1(7) . . ?
C00D C00M H00M 119.4 . . ?
C00F C00M H00M 119.4 . . ?
O10 C00N H00C 109.5 . . ?
O10 C00N H00D 109.5 . . ?
O10 C00N H00E 109.5 . . ?
H00C C00N H00D 109.5 . . ?
H00C C00N H00E 109.5 . . ?
H00D C00N H00E 109.5 . . ?
O005 C00O O10 124.7(7) . . ?
O005 C00O C00G 123.8(6) . . ?
O10 C00O C00G 111.5(6) . . ?
C008 C00P C00I 118.8(7) . . ?
C008 C00P H00P 120.6 . . ?
C00I C00P H00P 120.6 . . ?
O004 C00Q H00G 109.5 . . ?
O004 C00Q H00J 109.5 . . ?
O004 C00Q H00K 109.5 . . ?
H00G C00Q H00J 109.5 . . ?
H00G C00Q H00K 109.5 . . ?
H00J C00Q H00K 109.5 . . ?
Br02 C00R H00N 108.8 . . ?
Br02 C00R H00O 108.8 . . ?
C00E C00R Br02 113.8(6) . . ?
C00E C00R H00N 108.8 . . ?
C00E C00R H00O 108.8 . . ?
H00N C00R H00O 107.7 . . ?
Br01 C9 H9A 108.9 . . ?
Br01 C9 H9B 108.9 . . ?
C00C C9 Br01 113.3(5) . . ?
C00C C9 H9A 108.9 . . ?
C00C C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?

_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 3.037
_oxdiff_exptl_absorpt_empirical_full_min 0.675
