# Supplementary Information (SI) for Chemical Science.
# 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_lph1823d_0m
_database_code_depnum_ccdc_archive 'CCDC 2247992'
loop_
_audit_author_name
_audit_author_address
lipuhui
;fuzhou university
China
;
_audit_update_record             
;
2023-03-12 deposited with the CCDC.	2025-12-02 downloaded from the CCDC.
;
_audit_creation_date             2022-12-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H23 Br O2'
_chemical_formula_sum            'C20 H23 Br O2'
_chemical_formula_weight         375.29
_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/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   21.565(9)
_cell_length_b                   5.361(2)
_cell_length_c                   15.030(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.476(15)
_cell_angle_gamma                90
_cell_volume                     1729.7(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8004
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      24.033
_cell_measurement_theta_min      2.799
_shelx_estimated_absorpt_T_max   0.763
_shelx_estimated_absorpt_T_min   0.716
_exptl_absorpt_coefficient_mu    2.384
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5516
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1066 before and 0.0692 after correction.
The Ratio of minimum to maximum transmission is 0.7399.
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    1.441
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0843
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            33705
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.303
_diffrn_reflns_theta_min         2.723
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_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           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2625
_reflns_number_total             3835
_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  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3835
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.022
_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)+(0.0254P)²+1.5005P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0781
_refine_ls_wR_factor_ref         0.0893
_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:
 C006(H00A,H00B), C009(H00C,H00D), C00A(H00E,H00F), C00E(H00I,H00J)
2.b Aromatic/amide H refined with riding coordinates:
 C004(H004), C00B(H00G), C00C(H00H), C00F(H00K), C00G(H00L), C00J(H00M),
 C00K(H00N), C00L(H00O)
2.c Idealised Me refined as rotating group:
 C00M(H00P,H00Q,H00R), C00N(H00S,H00T,H00U)
2.d Idealised tetrahedral OH refined as rotating group:
 O003(H003)
;
_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 0.04259(2) 0.18052(6) 0.92532(2) 0.05032(13) Uani 1 1 d . . . . .
O002 O 0.22305(8) 0.7100(3) 0.70797(12) 0.0304(4) Uani 1 1 d . . . . .
O003 O 0.48675(9) 1.0326(3) 0.72472(12) 0.0300(4) Uani 1 1 d . . . . .
H003 H 0.500471 1.164354 0.749654 0.045 Uiso 1 1 calc R U . . .
C004 C 0.41331(12) 0.7668(4) 0.53873(16) 0.0239(6) Uani 1 1 d . . . . .
H004 H 0.446041 0.833964 0.508061 0.029 Uiso 1 1 calc R U . . .
C005 C 0.37914(12) 0.5603(5) 0.49149(16) 0.0247(6) Uani 1 1 d . . . . .
C006 C 0.35980(12) 0.8093(4) 0.68174(17) 0.0238(6) Uani 1 1 d . . . . .
H00A H 0.380893 0.810278 0.743199 0.029 Uiso 1 1 calc R U . . .
H00B H 0.344447 0.637937 0.668664 0.029 Uiso 1 1 calc R U . . .
C007 C 0.40638(12) 0.8765(4) 0.61715(17) 0.0224(6) Uani 1 1 d . . . . .
C008 C 0.18112(12) 0.6079(5) 0.76075(18) 0.0259(6) Uani 1 1 d . . . . .
C009 C 0.44812(13) 1.0937(5) 0.64492(17) 0.0260(6) Uani 1 1 d . . . . .
H00C H 0.474501 1.134465 0.596507 0.031 Uiso 1 1 calc R U . . .
H00D H 0.422456 1.241888 0.655645 0.031 Uiso 1 1 calc R U . . .
C00A C 0.25822(13) 0.9210(5) 0.74327(18) 0.0270(6) Uani 1 1 d . . . . .
H00E H 0.280522 0.879102 0.802006 0.032 Uiso 1 1 calc R U . . .
H00F H 0.230109 1.063570 0.751329 0.032 Uiso 1 1 calc R U . . .
C00B C 0.14172(12) 0.4281(5) 0.71949(18) 0.0275(6) Uani 1 1 d . . . . .
H00G H 0.143670 0.392490 0.657902 0.033 Uiso 1 1 calc R U . . .
C00C C 0.17720(12) 0.6683(5) 0.84943(17) 0.0276(6) Uani 1 1 d . . . . .
H00H H 0.203009 0.796393 0.876406 0.033 Uiso 1 1 calc R U . . .
C00D C 0.13576(13) 0.5434(5) 0.89987(18) 0.0308(6) Uani 1 1 d . . . . .
C00E C 0.30413(12) 0.9876(5) 0.67741(17) 0.0261(6) Uani 1 1 d . . . . .
H00I H 0.319459 1.159469 0.689676 0.031 Uiso 1 1 calc R U . . .
H00J H 0.282582 0.984802 0.616239 0.031 Uiso 1 1 calc R U . . .
C00F C 0.41044(13) 0.4257(5) 0.42942(17) 0.0283(6) Uani 1 1 d . . . . .
H00K H 0.451802 0.471469 0.419627 0.034 Uiso 1 1 calc R U . . .
C00G C 0.31775(13) 0.4944(5) 0.50185(17) 0.0281(6) Uani 1 1 d . . . . .
H00L H 0.295006 0.585979 0.542018 0.034 Uiso 1 1 calc R U . . .
C00H C 0.09960(13) 0.3000(5) 0.76679(19) 0.0311(6) Uani 1 1 d . . . . .
C00I C 0.09838(13) 0.3589(5) 0.8572(2) 0.0323(7) Uani 1 1 d . . . . .
C00J C 0.38247(14) 0.2280(5) 0.38220(18) 0.0314(7) Uani 1 1 d . . . . .
H00M H 0.404775 0.137216 0.341304 0.038 Uiso 1 1 calc R U . . .
C00K C 0.28940(13) 0.2965(5) 0.45417(18) 0.0307(6) Uani 1 1 d . . . . .
H00N H 0.247639 0.252632 0.462304 0.037 Uiso 1 1 calc R U . . .
C00L C 0.32191(14) 0.1629(5) 0.39471(19) 0.0339(7) Uani 1 1 d . . . . .
H00O H 0.302558 0.026664 0.362585 0.041 Uiso 1 1 calc R U . . .
C00M C 0.13457(15) 0.6067(6) 0.99722(19) 0.0423(8) Uani 1 1 d . . . . .
H00P H 0.161936 0.749645 1.012150 0.064 Uiso 1 1 calc R U . . .
H00Q H 0.149065 0.463008 1.033769 0.064 Uiso 1 1 calc R U . . .
H00R H 0.091919 0.648835 1.009151 0.064 Uiso 1 1 calc R U . . .
C00N C 0.05837(14) 0.1047(5) 0.7202(2) 0.0437(8) Uani 1 1 d . . . . .
H00S H 0.062928 0.108598 0.655995 0.066 Uiso 1 1 calc R U . . .
H00T H 0.014892 0.138246 0.730150 0.066 Uiso 1 1 calc R U . . .
H00U H 0.070395 -0.060229 0.744177 0.066 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
Br01 C00I 1.909(3) . ?
O002 C008 1.373(3) . ?
O002 C00A 1.435(3) . ?
O003 H003 0.8400 . ?
O003 C009 1.432(3) . ?
C004 H004 0.9500 . ?
C004 C005 1.474(4) . ?
C004 C007 1.338(3) . ?
C005 C00F 1.402(4) . ?
C005 C00G 1.393(4) . ?
C006 H00A 0.9900 . ?
C006 H00B 0.9900 . ?
C006 C007 1.506(3) . ?
C006 C00E 1.531(3) . ?
C007 C009 1.506(3) . ?
C008 C00B 1.391(4) . ?
C008 C00C 1.382(4) . ?
C009 H00C 0.9900 . ?
C009 H00D 0.9900 . ?
C00A H00E 0.9900 . ?
C00A H00F 0.9900 . ?
C00A C00E 1.508(3) . ?
C00B H00G 0.9500 . ?
C00B C00H 1.388(4) . ?
C00C H00H 0.9500 . ?
C00C C00D 1.397(4) . ?
C00D C00I 1.393(4) . ?
C00D C00M 1.505(4) . ?
C00E H00I 0.9900 . ?
C00E H00J 0.9900 . ?
C00F H00K 0.9500 . ?
C00F C00J 1.382(4) . ?
C00G H00L 0.9500 . ?
C00G C00K 1.389(4) . ?
C00H C00I 1.398(4) . ?
C00H C00N 1.503(4) . ?
C00J H00M 0.9500 . ?
C00J C00L 1.382(4) . ?
C00K H00N 0.9500 . ?
C00K C00L 1.387(4) . ?
C00L H00O 0.9500 . ?
C00M H00P 0.9800 . ?
C00M H00Q 0.9800 . ?
C00M H00R 0.9800 . ?
C00N H00S 0.9800 . ?
C00N H00T 0.9800 . ?
C00N H00U 0.9800 . ?

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
C008 O002 C00A 117.05(19) . . ?
C009 O003 H003 109.5 . . ?
C005 C004 H004 114.3 . . ?
C007 C004 H004 114.3 . . ?
C007 C004 C005 131.4(2) . . ?
C00F C005 C004 117.2(2) . . ?
C00G C005 C004 125.0(2) . . ?
C00G C005 C00F 117.8(2) . . ?
H00A C006 H00B 107.8 . . ?
C007 C006 H00A 109.0 . . ?
C007 C006 H00B 109.0 . . ?
C007 C006 C00E 113.1(2) . . ?
C00E C006 H00A 109.0 . . ?
C00E C006 H00B 109.0 . . ?
C004 C007 C006 126.9(2) . . ?
C004 C007 C009 118.0(2) . . ?
C006 C007 C009 115.1(2) . . ?
O002 C008 C00B 115.3(2) . . ?
O002 C008 C00C 124.6(2) . . ?
C00C C008 C00B 120.1(2) . . ?
O003 C009 C007 109.9(2) . . ?
O003 C009 H00C 109.7 . . ?
O003 C009 H00D 109.7 . . ?
C007 C009 H00C 109.7 . . ?
C007 C009 H00D 109.7 . . ?
H00C C009 H00D 108.2 . . ?
O002 C00A H00E 110.2 . . ?
O002 C00A H00F 110.2 . . ?
O002 C00A C00E 107.5(2) . . ?
H00E C00A H00F 108.5 . . ?
C00E C00A H00E 110.2 . . ?
C00E C00A H00F 110.2 . . ?
C008 C00B H00G 119.5 . . ?
C00H C00B C008 121.1(3) . . ?
C00H C00B H00G 119.5 . . ?
C008 C00C H00H 119.6 . . ?
C008 C00C C00D 120.8(3) . . ?
C00D C00C H00H 119.6 . . ?
C00C C00D C00M 119.4(3) . . ?
C00I C00D C00C 117.6(3) . . ?
C00I C00D C00M 123.0(3) . . ?
C006 C00E H00I 109.1 . . ?
C006 C00E H00J 109.1 . . ?
C00A C00E C006 112.7(2) . . ?
C00A C00E H00I 109.1 . . ?
C00A C00E H00J 109.1 . . ?
H00I C00E H00J 107.8 . . ?
C005 C00F H00K 119.3 . . ?
C00J C00F C005 121.5(3) . . ?
C00J C00F H00K 119.3 . . ?
C005 C00G H00L 119.6 . . ?
C00K C00G C005 120.8(3) . . ?
C00K C00G H00L 119.6 . . ?
C00B C00H C00I 117.4(3) . . ?
C00B C00H C00N 119.6(3) . . ?
C00I C00H C00N 123.0(3) . . ?
C00D C00I Br01 118.4(2) . . ?
C00D C00I C00H 123.0(3) . . ?
C00H C00I Br01 118.6(2) . . ?
C00F C00J H00M 120.1 . . ?
C00F C00J C00L 119.7(3) . . ?
C00L C00J H00M 120.1 . . ?
C00G C00K H00N 119.9 . . ?
C00L C00K C00G 120.2(3) . . ?
C00L C00K H00N 119.9 . . ?
C00J C00L C00K 120.0(3) . . ?
C00J C00L H00O 120.0 . . ?
C00K C00L H00O 120.0 . . ?
C00D C00M H00P 109.5 . . ?
C00D C00M H00Q 109.5 . . ?
C00D C00M H00R 109.5 . . ?
H00P C00M H00Q 109.5 . . ?
H00P C00M H00R 109.5 . . ?
H00Q C00M H00R 109.5 . . ?
C00H C00N H00S 109.5 . . ?
C00H C00N H00T 109.5 . . ?
C00H C00N H00U 109.5 . . ?
H00S C00N H00T 109.5 . . ?
H00S C00N H00U 109.5 . . ?
H00T C00N H00U 109.5 . . ?

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
O002 C008 C00B C00H 176.3(2) . . . . ?
O002 C008 C00C C00D -175.8(2) . . . . ?
O002 C00A C00E C006 -76.3(3) . . . . ?
C004 C005 C00F C00J 179.6(2) . . . . ?
C004 C005 C00G C00K 179.9(2) . . . . ?
C004 C007 C009 O003 -116.7(3) . . . . ?
C005 C004 C007 C006 1.3(4) . . . . ?
C005 C004 C007 C009 -177.5(2) . . . . ?
C005 C00F C00J C00L 1.2(4) . . . . ?
C005 C00G C00K C00L -0.6(4) . . . . ?
C006 C007 C009 O003 64.4(3) . . . . ?
C007 C004 C005 C00F -156.3(3) . . . . ?
C007 C004 C005 C00G 25.8(4) . . . . ?
C007 C006 C00E C00A -179.2(2) . . . . ?
C008 O002 C00A C00E 175.7(2) . . . . ?
C008 C00B C00H C00I 0.1(4) . . . . ?
C008 C00B C00H C00N -179.2(2) . . . . ?
C008 C00C C00D C00I -0.7(4) . . . . ?
C008 C00C C00D C00M 177.5(2) . . . . ?
C00A O002 C008 C00B 171.1(2) . . . . ?
C00A O002 C008 C00C -10.3(4) . . . . ?
C00B C008 C00C C00D 2.7(4) . . . . ?
C00B C00H C00I Br01 -178.40(19) . . . . ?
C00B C00H C00I C00D 2.1(4) . . . . ?
C00C C008 C00B C00H -2.4(4) . . . . ?
C00C C00D C00I Br01 178.71(19) . . . . ?
C00C C00D C00I C00H -1.7(4) . . . . ?
C00E C006 C007 C004 -102.1(3) . . . . ?
C00E C006 C007 C009 76.7(3) . . . . ?
C00F C005 C00G C00K 2.0(4) . . . . ?
C00F C00J C00L C00K 0.3(4) . . . . ?
C00G C005 C00F C00J -2.4(4) . . . . ?
C00G C00K C00L C00J -0.6(4) . . . . ?
C00M C00D C00I Br01 0.5(4) . . . . ?
C00M C00D C00I C00H -179.9(3) . . . . ?
C00N C00H C00I Br01 0.8(4) . . . . ?
C00N C00H C00I C00D -178.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
