# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_mo_dd23006_0m
_database_code_depnum_ccdc_archive 'CCDC 2340632'
loop_
_audit_author_name
_audit_author_address
HuTeng
;East China University of Science and Technology
China
;
_audit_update_record             
;
2024-03-15 deposited with the CCDC.	2024-05-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H18 Br2 O2'
_chemical_formula_weight         486.19

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.2643(5)
_cell_length_b                   9.0256(5)
_cell_length_c                   21.2231(13)
_cell_angle_alpha                90
_cell_angle_beta                 94.116(2)
_cell_angle_gamma                90
_cell_volume                     1961.07(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    6127
_cell_measurement_theta_min      5.334
_cell_measurement_theta_max      54.697

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    4.149
_shelx_estimated_absorpt_T_min   0.557
_shelx_estimated_absorpt_T_max   0.682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5165
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      213(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18359
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.667
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3855
_reflns_number_gt                2850
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0266P)²+1.2351P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3855
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0772
_refine_ls_wR_factor_gt          0.0681
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.84524(3) 0.27921(4) 0.39139(2) 0.05573(13) Uani 1 1 d . . . . .
Br2 Br 0.38176(3) 0.38578(5) 0.23902(2) 0.05627(14) Uani 1 1 d . . . . .
O1 O 0.34831(18) 0.6249(2) 0.33262(9) 0.0327(5) Uani 1 1 d . . . . .
O2 O 0.24548(18) 0.6199(2) 0.42684(9) 0.0347(5) Uani 1 1 d . . . . .
C1 C 0.4613(3) 0.5490(3) 0.34980(13) 0.0273(6) Uani 1 1 d . . . . .
C2 C 0.4941(3) 0.4332(3) 0.31061(14) 0.0311(7) Uani 1 1 d . . . . .
C3 C 0.6062(3) 0.3502(3) 0.32264(14) 0.0346(7) Uani 1 1 d . . . . .
H3 H 0.6266 0.2714 0.2961 0.041 Uiso 1 1 calc R U . . .
C4 C 0.6874(3) 0.3870(3) 0.37520(15) 0.0329(7) Uani 1 1 d . . . . .
C5 C 0.6565(3) 0.4995(3) 0.41513(14) 0.0313(7) Uani 1 1 d . . . . .
H5 H 0.7130 0.5213 0.4508 0.038 Uiso 1 1 calc R U . . .
C6 C 0.5427(3) 0.5816(3) 0.40344(13) 0.0263(6) Uani 1 1 d . . . . .
C7 C 0.5017(3) 0.6981(3) 0.44977(13) 0.0285(6) Uani 1 1 d . . . . .
H7 H 0.4553 0.6450 0.4823 0.034 Uiso 1 1 calc R U . . .
C8 C 0.4026(3) 0.8029(3) 0.41646(14) 0.0316(7) Uani 1 1 d . . . . .
H8A H 0.3654 0.8678 0.4476 0.038 Uiso 1 1 calc R U . . .
H8B H 0.4460 0.8651 0.3865 0.038 Uiso 1 1 calc R U . . .
C9 C 0.2941(3) 0.7140(3) 0.38154(13) 0.0288(6) Uani 1 1 d . . . . .
C10 C 0.1892(3) 0.8066(3) 0.34623(13) 0.0305(7) Uani 1 1 d . . . . .
C11 C 0.2243(3) 0.9154(4) 0.30470(15) 0.0408(8) Uani 1 1 d . . . . .
H11 H 0.3130 0.9301 0.2981 0.049 Uiso 1 1 calc R U . . .
C12 C 0.1303(3) 1.0034(4) 0.27259(15) 0.0490(9) Uani 1 1 d . . . . .
H12 H 0.1550 1.0763 0.2441 0.059 Uiso 1 1 calc R U . . .
C13 C 0.0001(3) 0.9824(4) 0.28298(17) 0.0517(10) Uani 1 1 d . . . . .
H13 H -0.0642 1.0426 0.2622 0.062 Uiso 1 1 calc R U . . .
C14 C -0.0352(3) 0.8733(4) 0.32369(16) 0.0453(9) Uani 1 1 d . . . . .
H14 H -0.1241 0.8587 0.3298 0.054 Uiso 1 1 calc R U . . .
C15 C 0.0579(3) 0.7840(3) 0.35610(15) 0.0358(7) Uani 1 1 d . . . . .
C16 C 0.0186(3) 0.6651(4) 0.39986(17) 0.0467(9) Uani 1 1 d . . . . .
H16A H -0.0632 0.6194 0.3829 0.056 Uiso 1 1 calc R U . . .
H16B H 0.0039 0.7081 0.4411 0.056 Uiso 1 1 calc R U . . .
C17 C 0.1242(3) 0.5489(4) 0.40734(17) 0.0421(8) Uani 1 1 d . . . . .
H17A H 0.1022 0.4758 0.4390 0.051 Uiso 1 1 calc R U . . .
H17B H 0.1319 0.4974 0.3671 0.051 Uiso 1 1 calc R U . . .
C18 C 0.6167(3) 0.7754(3) 0.48416(14) 0.0283(6) Uani 1 1 d . . . . .
C19 C 0.7012(3) 0.8658(4) 0.45377(16) 0.0432(8) Uani 1 1 d . . . . .
H19 H 0.6851 0.8863 0.4105 0.052 Uiso 1 1 calc R U . . .
C20 C 0.8102(3) 0.9264(4) 0.48722(19) 0.0501(9) Uani 1 1 d . . . . .
H20 H 0.8670 0.9875 0.4661 0.060 Uiso 1 1 calc R U . . .
C21 C 0.8357(3) 0.8986(3) 0.54995(18) 0.0451(9) Uani 1 1 d . . . . .
H21 H 0.9103 0.9388 0.5719 0.054 Uiso 1 1 calc R U . . .
C22 C 0.7522(4) 0.8119(4) 0.58047(17) 0.0489(9) Uani 1 1 d . . . . .
H22 H 0.7687 0.7930 0.6239 0.059 Uiso 1 1 calc R U . . .
C23 C 0.6427(3) 0.7513(3) 0.54821(15) 0.0407(8) Uani 1 1 d . . . . .
H23 H 0.5852 0.6928 0.5702 0.049 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 C4 1.900(3) . ?
Br2 C2 1.889(3) . ?
O1 C1 1.373(3) . ?
O1 C9 1.455(3) . ?
O2 C9 1.401(3) . ?
O2 C17 1.434(3) . ?
C1 C2 1.392(4) . ?
C1 C6 1.394(4) . ?
C2 C3 1.382(4) . ?
C3 C4 1.385(4) . ?
C3 H3 0.9400 . ?
C4 C5 1.374(4) . ?
C5 C6 1.390(4) . ?
C5 H5 0.9400 . ?
C6 C7 1.520(4) . ?
C7 C18 1.513(4) . ?
C7 C8 1.525(4) . ?
C7 H7 0.9900 . ?
C8 C9 1.521(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C9 C10 1.518(4) . ?
C10 C11 1.384(4) . ?
C10 C15 1.394(4) . ?
C11 C12 1.389(4) . ?
C11 H11 0.9400 . ?
C12 C13 1.383(5) . ?
C12 H12 0.9400 . ?
C13 C14 1.376(5) . ?
C13 H13 0.9400 . ?
C14 C15 1.394(4) . ?
C14 H14 0.9400 . ?
C15 C16 1.494(5) . ?
C16 C17 1.508(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C18 C19 1.384(4) . ?
C18 C23 1.383(4) . ?
C19 C20 1.392(4) . ?
C19 H19 0.9400 . ?
C20 C21 1.362(5) . ?
C20 H20 0.9400 . ?
C21 C22 1.359(5) . ?
C21 H21 0.9400 . ?
C22 C23 1.386(4) . ?
C22 H22 0.9400 . ?
C23 H23 0.9400 . ?

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
C1 O1 C9 116.4(2) . . ?
C9 O2 C17 114.6(2) . . ?
O1 C1 C2 116.8(2) . . ?
O1 C1 C6 123.9(2) . . ?
C2 C1 C6 119.3(2) . . ?
C3 C2 C1 122.0(3) . . ?
C3 C2 Br2 118.5(2) . . ?
C1 C2 Br2 119.4(2) . . ?
C2 C3 C4 117.6(3) . . ?
C2 C3 H3 121.2 . . ?
C4 C3 H3 121.2 . . ?
C5 C4 C3 121.5(3) . . ?
C5 C4 Br1 119.9(2) . . ?
C3 C4 Br1 118.6(2) . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 118.7(3) . . ?
C5 C6 C7 121.4(2) . . ?
C1 C6 C7 119.8(2) . . ?
C18 C7 C6 112.9(2) . . ?
C18 C7 C8 114.2(2) . . ?
C6 C7 C8 109.6(2) . . ?
C18 C7 H7 106.5 . . ?
C6 C7 H7 106.5 . . ?
C8 C7 H7 106.5 . . ?
C9 C8 C7 109.8(2) . . ?
C9 C8 H8A 109.7 . . ?
C7 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
O2 C9 O1 109.1(2) . . ?
O2 C9 C10 113.5(2) . . ?
O1 C9 C10 104.3(2) . . ?
O2 C9 C8 105.6(2) . . ?
O1 C9 C8 109.6(2) . . ?
C10 C9 C8 114.7(2) . . ?
C11 C10 C15 119.8(3) . . ?
C11 C10 C9 119.9(3) . . ?
C15 C10 C9 120.3(3) . . ?
C10 C11 C12 121.0(3) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C13 C12 C11 119.2(3) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C14 C13 C12 120.0(3) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 121.4(3) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C14 C15 C10 118.5(3) . . ?
C14 C15 C16 121.1(3) . . ?
C10 C15 C16 120.4(3) . . ?
C15 C16 C17 109.9(3) . . ?
C15 C16 H16A 109.7 . . ?
C17 C16 H16A 109.7 . . ?
C15 C16 H16B 109.7 . . ?
C17 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
O2 C17 C16 108.8(3) . . ?
O2 C17 H17A 109.9 . . ?
C16 C17 H17A 109.9 . . ?
O2 C17 H17B 109.9 . . ?
C16 C17 H17B 109.9 . . ?
H17A C17 H17B 108.3 . . ?
C19 C18 C23 117.9(3) . . ?
C19 C18 C7 122.7(3) . . ?
C23 C18 C7 119.4(3) . . ?
C18 C19 C20 120.1(3) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C21 C20 C19 121.2(3) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C22 C21 C20 119.2(3) . . ?
C22 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?
C21 C22 C23 120.6(3) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C18 C23 C22 121.0(3) . . ?
C18 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?

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
C9 O1 C1 C2 162.4(2) . . . . ?
C9 O1 C1 C6 -17.5(4) . . . . ?
O1 C1 C2 C3 179.2(3) . . . . ?
C6 C1 C2 C3 -0.9(4) . . . . ?
O1 C1 C2 Br2 -1.4(4) . . . . ?
C6 C1 C2 Br2 178.5(2) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
Br2 C2 C3 C4 179.8(2) . . . . ?
C2 C3 C4 C5 1.7(4) . . . . ?
C2 C3 C4 Br1 -177.9(2) . . . . ?
C3 C4 C5 C6 -0.8(4) . . . . ?
Br1 C4 C5 C6 178.8(2) . . . . ?
C4 C5 C6 C1 -1.0(4) . . . . ?
C4 C5 C6 C7 175.1(3) . . . . ?
O1 C1 C6 C5 -178.3(3) . . . . ?
C2 C1 C6 C5 1.8(4) . . . . ?
O1 C1 C6 C7 5.5(4) . . . . ?
C2 C1 C6 C7 -174.4(3) . . . . ?
C5 C6 C7 C18 33.0(4) . . . . ?
C1 C6 C7 C18 -151.0(3) . . . . ?
C5 C6 C7 C8 161.5(3) . . . . ?
C1 C6 C7 C8 -22.5(4) . . . . ?
C18 C7 C8 C9 177.9(2) . . . . ?
C6 C7 C8 C9 50.2(3) . . . . ?
C17 O2 C9 O1 -75.1(3) . . . . ?
C17 O2 C9 C10 40.7(3) . . . . ?
C17 O2 C9 C8 167.2(2) . . . . ?
C1 O1 C9 O2 -69.6(3) . . . . ?
C1 O1 C9 C10 168.8(2) . . . . ?
C1 O1 C9 C8 45.6(3) . . . . ?
C7 C8 C9 O2 54.5(3) . . . . ?
C7 C8 C9 O1 -63.0(3) . . . . ?
C7 C8 C9 C10 -179.8(2) . . . . ?
O2 C9 C10 C11 173.4(3) . . . . ?
O1 C9 C10 C11 -68.0(3) . . . . ?
C8 C9 C10 C11 51.8(4) . . . . ?
O2 C9 C10 C15 -5.7(4) . . . . ?
O1 C9 C10 C15 112.9(3) . . . . ?
C8 C9 C10 C15 -127.3(3) . . . . ?
C15 C10 C11 C12 0.2(5) . . . . ?
C9 C10 C11 C12 -178.9(3) . . . . ?
C10 C11 C12 C13 0.7(5) . . . . ?
C11 C12 C13 C14 -1.4(5) . . . . ?
C12 C13 C14 C15 1.3(5) . . . . ?
C13 C14 C15 C10 -0.4(5) . . . . ?
C13 C14 C15 C16 -179.5(3) . . . . ?
C11 C10 C15 C14 -0.3(4) . . . . ?
C9 C10 C15 C14 178.8(3) . . . . ?
C11 C10 C15 C16 178.8(3) . . . . ?
C9 C10 C15 C16 -2.1(4) . . . . ?
C14 C15 C16 C17 156.9(3) . . . . ?
C10 C15 C16 C17 -22.3(4) . . . . ?
C9 O2 C17 C16 -66.8(3) . . . . ?
C15 C16 C17 O2 54.3(4) . . . . ?
C6 C7 C18 C19 66.0(4) . . . . ?
C8 C7 C18 C19 -60.0(4) . . . . ?
C6 C7 C18 C23 -111.4(3) . . . . ?
C8 C7 C18 C23 122.5(3) . . . . ?
C23 C18 C19 C20 1.6(5) . . . . ?
C7 C18 C19 C20 -175.9(3) . . . . ?
C18 C19 C20 C21 -0.1(5) . . . . ?
C19 C20 C21 C22 -1.0(5) . . . . ?
C20 C21 C22 C23 0.6(5) . . . . ?
C19 C18 C23 C22 -2.0(5) . . . . ?
C7 C18 C23 C22 175.6(3) . . . . ?
C21 C22 C23 C18 1.0(5) . . . . ?

_refine_diff_density_max         0.514
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.064

_shelxl_version_number           2013-4

