# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2026

####################################################################### 
# 
# 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_230329zh_xj_3_39_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2361001'
loop_
_audit_author_name
_audit_author_address
'Sun Zhihui'
;Nanjing University of Chinese Medicine
China
;
_audit_update_record             
;
2024-06-06 deposited with the CCDC.	2026-04-23 downloaded from the CCDC.
;
_audit_creation_date             2023-04-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H25 Br O2'
_chemical_formula_sum            'C19 H25 Br O2'
_chemical_formula_weight         365.30
_chemical_absolute_configuration AD
_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 0.0148 0.0070 '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 -0.9502 1.0410 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.8573(2)
_cell_length_b                   15.9633(4)
_cell_length_c                   17.6718(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1652.35(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9891
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      53.80
_cell_measurement_theta_min      3.25
_shelx_estimated_absorpt_T_max   0.817
_shelx_estimated_absorpt_T_min   0.766
_exptl_absorpt_coefficient_mu    2.346
_exptl_absorpt_correction_T_max  0.7506
_exptl_absorpt_correction_T_min  0.6440
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0927 before and 0.0545 after correction.
The Ratio of minimum to maximum transmission is 0.8580.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21054
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         53.988
_diffrn_reflns_theta_min         3.246
_diffrn_ambient_temperature      193.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.705
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2848
_reflns_number_total             3023
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1132 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.019(8)
_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     201
_refine_ls_number_reflns         3023
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0227
_refine_ls_restrained_S_all      1.051
_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)+(0.0223P)²+0.5928P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0524
_refine_ls_wR_factor_ref         0.0536
_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 Ternary CH refined with riding coordinates:
 C18(H18), C17(H17), C9(H9), C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C10(H10A,H10B), C11(H11A,H11B), C19(H19A,H19B), C15(H15A,
 H15B), C6(H6A,H6B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C13(H13A,H13B,H13C)
;
_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 0.34200(7) 0.40362(2) 0.81144(2) 0.04097(12) Uani 1 1 d . . . . .
O2 O 0.6736(5) 0.66932(13) 0.43414(11) 0.0385(5) Uani 1 1 d . . . . .
C18 C 0.5876(5) 0.47829(16) 0.64593(15) 0.0198(6) Uani 1 1 d . . . . .
H18 H 0.419027 0.481638 0.654429 0.024 Uiso 1 1 calc R . . . .
C17 C 0.6651(6) 0.55499(16) 0.60233(14) 0.0209(6) Uani 1 1 d . . . . .
H17 H 0.832329 0.547359 0.593230 0.025 Uiso 1 1 calc R . . . .
C16 C 0.6379(6) 0.64247(16) 0.63653(15) 0.0280(7) Uani 1 1 d . . . . .
H16A H 0.749945 0.652087 0.677566 0.034 Uiso 1 1 calc R . . . .
H16B H 0.481852 0.650895 0.656639 0.034 Uiso 1 1 calc R . . . .
C9 C 0.6422(5) 0.39923(16) 0.59878(13) 0.0204(5) Uani 1 1 d . . . . .
H9 H 0.812365 0.396580 0.595045 0.025 Uiso 1 1 calc R . . . .
C1 C 0.6530(5) 0.39415(17) 0.76547(14) 0.0264(6) Uani 1 1 d . . . . .
H1 H 0.766011 0.388645 0.807592 0.032 Uiso 1 1 calc R . . . .
C12 C 0.5544(5) 0.56198(18) 0.52367(15) 0.0232(6) Uani 1 1 d . . . . .
C10 C 0.5535(5) 0.40573(19) 0.51674(14) 0.0295(6) Uani 1 1 d . . . . .
H10A H 0.612320 0.357493 0.487415 0.035 Uiso 1 1 calc R . . . .
H10B H 0.384847 0.401861 0.517285 0.035 Uiso 1 1 calc R . . . .
C8 C 0.3043(5) 0.30767(18) 0.64100(17) 0.0282(7) Uani 1 1 d . . . . .
H8A H 0.236758 0.360442 0.658351 0.042 Uiso 1 1 calc GR . . . .
H8B H 0.262518 0.262562 0.675968 0.042 Uiso 1 1 calc GR . . . .
H8C H 0.247141 0.294452 0.590265 0.042 Uiso 1 1 calc GR . . . .
O1 O 0.9026(5) 0.11196(15) 0.73766(17) 0.0662(8) Uani 1 1 d . . . . .
C11 C 0.6233(6) 0.48712(17) 0.47643(15) 0.0288(7) Uani 1 1 d . . . . .
H11A H 0.790520 0.487644 0.468379 0.035 Uiso 1 1 calc R . . . .
H11B H 0.547981 0.490102 0.426343 0.035 Uiso 1 1 calc R . . . .
C19 C 0.7087(5) 0.47297(17) 0.72226(15) 0.0263(7) Uani 1 1 d . . . . .
H19A H 0.875623 0.475590 0.713889 0.032 Uiso 1 1 calc R . . . .
H19B H 0.664901 0.522073 0.753254 0.032 Uiso 1 1 calc R . . . .
C7 C 0.5667(5) 0.31641(17) 0.63848(15) 0.0202(6) Uani 1 1 d . . . . .
C14 C 0.6424(6) 0.64730(17) 0.49880(16) 0.0262(6) Uani 1 1 d . . . . .
C15 C 0.6843(6) 0.70020(17) 0.56856(16) 0.0328(7) Uani 1 1 d . . . . .
H15A H 0.580144 0.749032 0.569395 0.039 Uiso 1 1 calc R . . . .
H15B H 0.843794 0.720704 0.569525 0.039 Uiso 1 1 calc R . . . .
C2 C 0.6640(5) 0.31575(16) 0.71882(14) 0.0212(6) Uani 1 1 d . . . . .
C3 C 0.7719(5) 0.24977(18) 0.74870(17) 0.0264(6) Uani 1 1 d . . . . .
H3 H 0.840433 0.256136 0.797077 0.032 Uiso 1 1 calc R . . . .
C13 C 0.2928(5) 0.5722(2) 0.52777(17) 0.0347(8) Uani 1 1 d . . . . .
H13A H 0.226157 0.523362 0.553146 0.052 Uiso 1 1 calc GR . . . .
H13B H 0.230612 0.576643 0.476450 0.052 Uiso 1 1 calc GR . . . .
H13C H 0.255432 0.622973 0.556336 0.052 Uiso 1 1 calc GR . . . .
C6 C 0.6643(6) 0.24113(16) 0.59481(15) 0.0274(6) Uani 1 1 d . . . . .
H6A H 0.576662 0.233987 0.547350 0.033 Uiso 1 1 calc R . . . .
H6B H 0.824540 0.253433 0.580873 0.033 Uiso 1 1 calc R . . . .
C5 C 0.6576(7) 0.15904(17) 0.63913(16) 0.0309(7) Uani 1 1 d . . . . .
H5A H 0.497361 0.144198 0.650876 0.037 Uiso 1 1 calc R . . . .
H5B H 0.723978 0.113452 0.608169 0.037 Uiso 1 1 calc R . . . .
C4 C 0.7905(5) 0.16824(19) 0.71118(18) 0.0333(8) Uani 1 1 d . . . . .


_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 2.000(3) . ?
O2 C14 1.209(3) . ?
C18 C17 1.516(4) . ?
C18 C9 1.546(4) . ?
C18 C19 1.526(4) . ?
C17 C16 1.530(4) . ?
C17 C12 1.538(4) . ?
C16 C15 1.538(4) . ?
C9 C10 1.543(3) . ?
C9 C7 1.561(4) . ?
C1 C19 1.507(4) . ?
C1 C2 1.500(4) . ?
C12 C11 1.513(4) . ?
C12 C14 1.521(4) . ?
C12 C13 1.542(4) . ?
C10 C11 1.537(4) . ?
C8 C7 1.544(4) . ?
O1 C4 1.207(4) . ?
C7 C2 1.530(4) . ?
C7 C6 1.538(4) . ?
C14 C15 1.514(4) . ?
C2 C3 1.337(4) . ?
C3 C4 1.465(4) . ?
C6 C5 1.527(4) . ?
C5 C4 1.499(4) . ?

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
C17 C18 C9 108.9(2) . . ?
C17 C18 C19 110.8(2) . . ?
C19 C18 C9 109.6(2) . . ?
C18 C17 C16 120.3(2) . . ?
C18 C17 C12 113.0(2) . . ?
C16 C17 C12 104.3(2) . . ?
C17 C16 C15 102.7(2) . . ?
C18 C9 C7 113.00(19) . . ?
C10 C9 C18 112.4(2) . . ?
C10 C9 C7 112.6(2) . . ?
C19 C1 Br1 109.9(2) . . ?
C2 C1 Br1 109.0(2) . . ?
C2 C1 C19 114.1(2) . . ?
C17 C12 C13 112.6(2) . . ?
C11 C12 C17 109.2(2) . . ?
C11 C12 C14 117.2(2) . . ?
C11 C12 C13 112.0(3) . . ?
C14 C12 C17 100.5(2) . . ?
C14 C12 C13 104.8(2) . . ?
C11 C10 C9 113.8(2) . . ?
C12 C11 C10 109.9(2) . . ?
C1 C19 C18 113.2(2) . . ?
C8 C7 C9 111.8(2) . . ?
C2 C7 C9 108.5(2) . . ?
C2 C7 C8 110.1(2) . . ?
C2 C7 C6 108.8(2) . . ?
C6 C7 C9 109.3(2) . . ?
C6 C7 C8 108.3(2) . . ?
O2 C14 C12 125.8(3) . . ?
O2 C14 C15 125.6(3) . . ?
C15 C14 C12 108.6(2) . . ?
C14 C15 C16 105.8(2) . . ?
C1 C2 C7 119.2(2) . . ?
C3 C2 C1 117.4(2) . . ?
C3 C2 C7 123.2(2) . . ?
C2 C3 C4 123.8(3) . . ?
C5 C6 C7 113.8(2) . . ?
C4 C5 C6 109.8(2) . . ?
O1 C4 C3 121.8(3) . . ?
O1 C4 C5 122.6(3) . . ?
C3 C4 C5 115.6(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
