# 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. 
# 
#######################################################################

data_mo_lb_wz_14091_a
_audit_block_doi                 10.5517/ccdc.csd.cc2pn6p8
_database_code_depnum_ccdc_archive 'CCDC 2492080'
loop_
_audit_author_name
_audit_author_address
'Zhuang Wang'
;Sichuan University
China
;
_audit_update_record             
;
2025-09-29 deposited with the CCDC.	2026-01-08 downloaded from the CCDC.
;
_audit_creation_date             2025-09-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H21 Br O'
_chemical_formula_sum            'C14 H20 Br N O'
_chemical_formula_weight         298.22
_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'
N N 0.0061 0.0033 '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                   8.7790(16)
_cell_length_b                   13.881(2)
_cell_length_c                   11.429(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.759(7)
_cell_angle_gamma                90
_cell_volume                     1391.2(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6213
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.066
_cell_measurement_theta_min      2.748
_shelx_estimated_absorpt_T_max   0.701
_shelx_estimated_absorpt_T_min   0.351
_exptl_absorpt_coefficient_mu    2.940
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4259
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1365 before and 0.0868 after correction.
The Ratio of minimum to maximum transmission is 0.5712.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1085
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            34092
_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         27.527
_diffrn_reflns_theta_min         2.310
_diffrn_ambient_temperature      294.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-IICCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2328
_reflns_number_total             3204
_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 V8.41 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.41 (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.760
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         3204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0440
_refine_ls_restrained_S_all      1.033
_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)+(0.0558P)²+0.8885P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1270
_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:
 C1(H1), C4(H4), C5(H5), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C2(H2A,H2B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C10(H10A,
 H10B), C11(H11A,H11B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14)
;
_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
Br1 Br 0.53566(4) 0.58863(2) 0.11893(3) 0.06547(17) Uani 1 1 d . . . . .
O1 O 0.0448(3) 0.6826(3) 0.2109(3) 0.0984(10) Uani 1 1 d . . . . .
C1 C 0.4272(3) 0.74721(19) 0.3093(2) 0.0397(6) Uani 1 1 d . . . . .
H1 H 0.3766 0.7199 0.2385 0.048 Uiso 1 1 calc R U . . .
C15 C 0.6903(6) 0.8736(4) 0.3823(4) 0.0886(14) Uani 1 1 d . . . . .
H15A H 0.7533 0.9054 0.4428 0.106 Uiso 1 1 calc R U . . .
H15B H 0.7303 0.8894 0.3070 0.106 Uiso 1 1 calc R U . . .
C2 C 0.6971(4) 0.7663(3) 0.4006(4) 0.0752(11) Uani 1 1 d . . . . .
H2A H 0.6667 0.7507 0.4788 0.090 Uiso 1 1 calc R U . . .
H2B H 0.8008 0.7438 0.3929 0.090 Uiso 1 1 calc R U . . .
C3 C 0.5920(3) 0.7168(2) 0.3109(3) 0.0497(7) Uani 1 1 d . . . . .
C4 C 0.3448(3) 0.7072(2) 0.4151(2) 0.0422(6) Uani 1 1 d . . . . .
H4 H 0.3749 0.7457 0.4843 0.051 Uiso 1 1 calc R U . . .
C5 C 0.1655(4) 0.7081(2) 0.3992(3) 0.0540(7) Uani 1 1 d . . . . .
H5 H 0.1270 0.7549 0.4548 0.065 Uiso 1 1 calc R U . . .
C6 C 0.1130(5) 0.6085(3) 0.4362(5) 0.0815(12) Uani 1 1 d . . . . .
H6A H 0.0246 0.6135 0.4835 0.098 Uiso 1 1 calc R U . . .
H6B H 0.0866 0.5692 0.3680 0.098 Uiso 1 1 calc R U . . .
C7 C 0.3809(4) 0.6015(2) 0.4417(3) 0.0558(8) Uani 1 1 d . . . . .
H7A H 0.3923 0.5655 0.3699 0.067 Uiso 1 1 calc R U . . .
H7B H 0.4740 0.5956 0.4904 0.067 Uiso 1 1 calc R U . . .
C8 C 0.2452(5) 0.5654(3) 0.5058(4) 0.0775(11) Uani 1 1 d . . . . .
H8A H 0.2403 0.4956 0.5052 0.093 Uiso 1 1 calc R U . . .
H8B H 0.2486 0.5880 0.5862 0.093 Uiso 1 1 calc R U . . .
C9 C 0.1093(4) 0.7386(3) 0.2769(3) 0.0647(10) Uani 1 1 d . . . . .
C10 C 0.1355(5) 0.8419(3) 0.2423(4) 0.0769(12) Uani 1 1 d . . . . .
H10A H 0.1600 0.8429 0.1604 0.092 Uiso 1 1 calc R U . . .
H10B H 0.0404 0.8766 0.2487 0.092 Uiso 1 1 calc R U . . .
C11 C 0.2575(5) 0.8957(3) 0.3105(4) 0.0722(11) Uani 1 1 d . . . . .
H11A H 0.2346 0.8940 0.3926 0.087 Uiso 1 1 calc R U . . .
H11B H 0.2544 0.9625 0.2857 0.087 Uiso 1 1 calc R U . . .
C12 C 0.4172(4) 0.8581(2) 0.2985(3) 0.0537(8) Uani 1 1 d . . . . .
H12 H 0.4476 0.8751 0.2197 0.064 Uiso 1 1 calc R U . . .
C13 C 0.5287(7) 0.9092(3) 0.3863(4) 0.0796(12) Uani 1 1 d . . . . .
H13A H 0.5270 0.9778 0.3700 0.096 Uiso 1 1 calc R U . . .
H13B H 0.4940 0.9000 0.4648 0.096 Uiso 1 1 calc R U . . .
C14 C 0.6501(4) 0.6555(3) 0.2377(3) 0.0579(8) Uani 1 1 d . . . . .
H14 H 0.7546 0.6442 0.2446 0.069 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 C14 1.892(4) . ?
O1 C9 1.205(5) . ?
C1 H1 0.9800 . ?
C1 C3 1.507(4) . ?
C1 C4 1.542(4) . ?
C1 C12 1.546(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C2 1.504(6) . ?
C15 C13 1.505(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.511(5) . ?
C3 C14 1.313(5) . ?
C4 H4 0.9800 . ?
C4 C5 1.576(4) . ?
C4 C7 1.529(4) . ?
C5 H5 0.9800 . ?
C5 C6 1.523(5) . ?
C5 C9 1.521(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C8 1.499(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.514(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.508(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.493(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.509(5) . ?
C12 H12 0.9800 . ?
C12 C13 1.541(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14 0.9300 . ?

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
C3 C1 H1 107.3 . . ?
C3 C1 C4 112.1(2) . . ?
C3 C1 C12 109.3(2) . . ?
C4 C1 H1 107.3 . . ?
C4 C1 C12 113.2(2) . . ?
C12 C1 H1 107.3 . . ?
H15A C15 H15B 108.1 . . ?
C2 C15 H15A 109.5 . . ?
C2 C15 H15B 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 C2 110.7(3) . . ?
C15 C2 H2A 109.7 . . ?
C15 C2 H2B 109.7 . . ?
C15 C2 C3 109.7(3) . . ?
H2A C2 H2B 108.2 . . ?
C3 C2 H2A 109.7 . . ?
C3 C2 H2B 109.7 . . ?
C1 C3 C2 115.8(3) . . ?
C14 C3 C1 125.2(3) . . ?
C14 C3 C2 118.9(3) . . ?
C1 C4 H4 108.6 . . ?
C1 C4 C5 114.2(2) . . ?
C5 C4 H4 108.6 . . ?
C7 C4 C1 113.6(2) . . ?
C7 C4 H4 108.6 . . ?
C7 C4 C5 103.1(2) . . ?
C4 C5 H5 107.7 . . ?
C6 C5 C4 106.0(3) . . ?
C6 C5 H5 107.7 . . ?
C9 C5 C4 112.7(2) . . ?
C9 C5 H5 107.7 . . ?
C9 C5 C6 114.7(3) . . ?
C5 C6 H6A 110.6 . . ?
C5 C6 H6B 110.6 . . ?
H6A C6 H6B 108.7 . . ?
C8 C6 C5 105.8(3) . . ?
C8 C6 H6A 110.6 . . ?
C8 C6 H6B 110.6 . . ?
C4 C7 H7A 110.8 . . ?
C4 C7 H7B 110.8 . . ?
H7A C7 H7B 108.9 . . ?
C8 C7 C4 104.7(3) . . ?
C8 C7 H7A 110.8 . . ?
C8 C7 H7B 110.8 . . ?
C6 C8 C7 102.6(3) . . ?
C6 C8 H8A 111.2 . . ?
C6 C8 H8B 111.2 . . ?
C7 C8 H8A 111.2 . . ?
C7 C8 H8B 111.2 . . ?
H8A C8 H8B 109.2 . . ?
O1 C9 C5 121.2(4) . . ?
O1 C9 C10 121.5(4) . . ?
C10 C9 C5 117.3(3) . . ?
C9 C10 H10A 108.1 . . ?
C9 C10 H10B 108.1 . . ?
H10A C10 H10B 107.3 . . ?
C11 C10 C9 116.9(3) . . ?
C11 C10 H10A 108.1 . . ?
C11 C10 H10B 108.1 . . ?
C10 C11 H11A 108.5 . . ?
C10 C11 H11B 108.5 . . ?
C10 C11 C12 115.2(3) . . ?
H11A C11 H11B 107.5 . . ?
C12 C11 H11A 108.5 . . ?
C12 C11 H11B 108.5 . . ?
C1 C12 H12 107.2 . . ?
C11 C12 C1 112.7(3) . . ?
C11 C12 H12 107.2 . . ?
C11 C12 C13 110.2(3) . . ?
C13 C12 C1 112.0(3) . . ?
C13 C12 H12 107.2 . . ?
C15 C13 C12 113.5(3) . . ?
C15 C13 H13A 108.9 . . ?
C15 C13 H13B 108.9 . . ?
C12 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
Br1 C14 H14 117.8 . . ?
C3 C14 Br1 124.4(2) . . ?
C3 C14 H14 117.8 . . ?

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
O1 C9 C10 C11 -160.3(4) . . . . ?
C1 C3 C14 Br1 -2.9(5) . . . . ?
C1 C4 C5 C6 132.3(3) . . . . ?
C1 C4 C5 C9 6.0(4) . . . . ?
C1 C4 C7 C8 -155.5(3) . . . . ?
C1 C12 C13 C15 51.9(4) . . . . ?
C15 C2 C3 C1 -57.3(4) . . . . ?
C15 C2 C3 C14 119.3(4) . . . . ?
C2 C15 C13 C12 -55.5(5) . . . . ?
C2 C3 C14 Br1 -179.1(3) . . . . ?
C3 C1 C4 C5 -161.8(2) . . . . ?
C3 C1 C4 C7 -43.9(3) . . . . ?
C3 C1 C12 C11 -173.3(3) . . . . ?
C3 C1 C12 C13 -48.3(4) . . . . ?
C4 C1 C3 C2 -73.4(3) . . . . ?
C4 C1 C3 C14 110.2(3) . . . . ?
C4 C1 C12 C11 -47.6(4) . . . . ?
C4 C1 C12 C13 77.4(4) . . . . ?
C4 C5 C6 C8 17.5(4) . . . . ?
C4 C5 C9 O1 112.7(4) . . . . ?
C4 C5 C9 C10 -68.2(4) . . . . ?
C4 C7 C8 C6 43.0(4) . . . . ?
C5 C4 C7 C8 -31.4(3) . . . . ?
C5 C6 C8 C7 -37.1(4) . . . . ?
C5 C9 C10 C11 20.6(5) . . . . ?
C6 C5 C9 O1 -8.8(5) . . . . ?
C6 C5 C9 C10 170.3(3) . . . . ?
C7 C4 C5 C6 8.6(4) . . . . ?
C7 C4 C5 C9 -117.7(3) . . . . ?
C9 C5 C6 C8 142.6(3) . . . . ?
C9 C10 C11 C12 64.8(4) . . . . ?
C10 C11 C12 C1 -45.6(4) . . . . ?
C10 C11 C12 C13 -171.6(3) . . . . ?
C11 C12 C13 C15 178.3(3) . . . . ?
C12 C1 C3 C2 52.9(3) . . . . ?
C12 C1 C3 C14 -123.5(3) . . . . ?
C12 C1 C4 C5 74.1(3) . . . . ?
C12 C1 C4 C7 -168.1(3) . . . . ?
C13 C15 C2 C3 55.9(5) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
