# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_2
_database_code_depnum_ccdc_archive 'CCDC 2432267'
loop_
_audit_author_name
_audit_author_address
xwliBrisoq
;Guangdong University of Technology
China
;
_audit_update_record             
;
2025-03-19 deposited with the CCDC.	2025-04-24 downloaded from the CCDC.
;
_audit_creation_date             2025-03-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H17 Br N O'
_chemical_formula_sum            'C16 H17 Br N O'
_chemical_formula_weight         319.21
_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'
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'
Br Br -0.2901 2.4595 '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           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   10.4124(2)
_cell_length_b                   6.88590(10)
_cell_length_c                   10.4141(2)
_cell_angle_alpha                90
_cell_angle_beta                 112.8860(10)
_cell_angle_gamma                90
_cell_volume                     687.90(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4688
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.36
_cell_measurement_theta_min      3.54
_shelx_estimated_absorpt_T_max   0.916
_shelx_estimated_absorpt_T_min   0.865
_exptl_absorpt_coefficient_mu    2.979
_exptl_absorpt_correction_T_max  0.9159
_exptl_absorpt_correction_T_min  0.8653
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellowish
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             326
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8812
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.127
_diffrn_reflns_theta_min         3.540
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1533
_reflns_number_total             1979
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.880
_refine_diff_density_min         -0.628
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1979
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0471
_refine_ls_restrained_S_all      1.045
_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)+(0.0167P)²+1.3491P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.1030
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H13A,H13B} of C13, {H12A,H12B} of C12, {H14A,H14B} of C14
 At 1.5 times of:
  All O(H) groups, {H10A,H10B} of C10
2. Others
 Fixed Sof: H10B(0.5)
3.a Riding coordinates:
 C10(H10A,H10B)
3.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C8(H8), C9(H9)
3.d Tetrahedral OH refined with riding coordinates:
 O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.89166(5) 0.2500 0.02604(6) 0.05759(18) Uani 1 2 d S T P . .
O1 O 0.4487(3) 0.2500 0.4809(3) 0.0809(14) Uani 1 2 d S T P . .
H1 H 0.4247 0.2500 0.5472 0.121 Uiso 1 2 calc R U P . .
N1 N 0.2642(3) 0.2500 0.1021(3) 0.0403(7) Uani 1 2 d S T P . .
C1 C 0.3725(4) 0.2500 0.2303(4) 0.0386(8) Uani 1 2 d S T P . .
C2 C 0.5087(4) 0.2500 0.2456(4) 0.0400(9) Uani 1 2 d S T P . .
H2 H 0.5797 0.2500 0.3340 0.048 Uiso 1 2 calc R U P . .
C3 C 0.5408(4) 0.2500 0.1257(4) 0.0366(8) Uani 1 2 d S T P . .
C4 C 0.4311(4) 0.2500 -0.0062(4) 0.0342(7) Uani 1 2 d S T P . .
C5 C 0.2910(4) 0.2500 -0.0108(4) 0.0382(8) Uani 1 2 d S T P . .
C6 C 0.6810(4) 0.2500 0.1350(4) 0.0402(9) Uani 1 2 d S T P . .
H6 H 0.7550 0.2500 0.2215 0.048 Uiso 1 2 calc R U P . .
C7 C 0.7051(4) 0.2500 0.0155(5) 0.0418(9) Uani 1 2 d S T P . .
C8 C 0.5970(5) 0.2500 -0.1160(4) 0.0439(9) Uani 1 2 d S T P . .
H8 H 0.6166 0.2500 -0.1958 0.053 Uiso 1 2 calc R U P . .
C9 C 0.4621(4) 0.2500 -0.1265(4) 0.0416(9) Uani 1 2 d S T P . .
H9 H 0.3897 0.2500 -0.2141 0.050 Uiso 1 2 calc R U P . .
C10 C 0.1684(4) 0.2500 -0.1482(4) 0.0492(10) Uani 1 2 d S T P . .
H10A H 0.0837 0.2500 -0.1321 0.074 Uiso 1 2 d R U P . .
H10B H 0.1716 0.3638 -0.2001 0.074 Uiso 0.5 1 d R U P . .
C11 C 0.3277(4) 0.2500 0.3535(4) 0.0405(9) Uani 1 2 d S T P . .
C12 C 0.2431(4) 0.0691(5) 0.3503(3) 0.0524(8) Uani 1 1 d . . . . .
H12A H 0.3021 -0.0443 0.3629 0.063 Uiso 1 1 calc R U . . .
H12B H 0.1673 0.0589 0.2595 0.063 Uiso 1 1 calc R U . . .
C13 C 0.1833(4) 0.0703(6) 0.4623(4) 0.0647(10) Uani 1 1 d . . . . .
H13A H 0.1246 -0.0431 0.4513 0.078 Uiso 1 1 calc R U . . .
H13B H 0.2589 0.0630 0.5534 0.078 Uiso 1 1 calc R U . . .
C14 C 0.0992(5) 0.2500 0.4543(5) 0.0660(15) Uani 1 2 d S T P . .
H14A H 0.0674 0.2500 0.5304 0.079 Uiso 1 2 calc R U P . .
H14B H 0.0178 0.2500 0.3674 0.079 Uiso 1 2 calc R U P . .


_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 C7 1.902(4) . ?
O1 H1 0.8200 . ?
O1 C11 1.431(5) . ?
N1 C1 1.372(5) . ?
N1 C5 1.310(5) . ?
C1 C2 1.364(5) . ?
C1 C11 1.526(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.413(5) . ?
C3 C4 1.404(5) . ?
C3 C6 1.425(5) . ?
C4 C5 1.441(5) . ?
C4 C9 1.410(5) . ?
C5 C10 1.502(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.362(5) . ?
C7 C8 1.394(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.367(6) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9601 . ?
C10 H10B 0.9600 . ?
C11 C12 1.518(4) 4_565 ?
C11 C12 1.518(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.522(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.499(5) . ?
C14 C13 1.499(5) 4_565 ?
C14 H14A 0.9700 . ?
C14 H14B 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
C11 O1 H1 109.5 . . ?
C5 N1 C1 119.4(3) . . ?
N1 C1 C11 114.4(3) . . ?
C2 C1 N1 122.5(3) . . ?
C2 C1 C11 123.1(3) . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.3(4) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 C6 121.9(4) . . ?
C4 C3 C2 118.8(3) . . ?
C4 C3 C6 119.3(3) . . ?
C3 C4 C5 117.5(3) . . ?
C3 C4 C9 119.3(3) . . ?
C9 C4 C5 123.3(4) . . ?
N1 C5 C4 122.4(3) . . ?
N1 C5 C10 117.2(3) . . ?
C4 C5 C10 120.4(3) . . ?
C3 C6 H6 120.5 . . ?
C7 C6 C3 119.1(4) . . ?
C7 C6 H6 120.5 . . ?
C6 C7 Br1 119.6(3) . . ?
C6 C7 C8 122.2(4) . . ?
C8 C7 Br1 118.2(3) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 C7 119.4(4) . . ?
C9 C8 H8 120.3 . . ?
C4 C9 H9 119.6 . . ?
C8 C9 C4 120.8(4) . . ?
C8 C9 H9 119.6 . . ?
C5 C10 H10A 109.4 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O1 C11 C1 109.4(3) . . ?
O1 C11 C12 108.3(2) . 4_565 ?
O1 C11 C12 108.3(2) . . ?
C12 C11 C1 110.2(2) . . ?
C12 C11 C1 110.2(2) 4_565 . ?
C12 C11 C12 110.3(3) . 4_565 ?
C11 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
C11 C12 C13 112.7(3) . . ?
H12A C12 H12B 107.8 . . ?
C13 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C12 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 C12 111.5(3) . . ?
C14 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C13 C14 C13 111.3(4) . 4_565 ?
C13 C14 H14A 109.4 4_565 . ?
C13 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
C13 C14 H14B 109.4 4_565 . ?
H14A C14 H14B 108.0 . . ?

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
Br1 C7 C8 C9 180.000(0) . . . . ?
O1 C11 C12 C13 66.0(4) . . . . ?
N1 C1 C2 C3 0.000(1) . . . . ?
N1 C1 C11 O1 180.000(1) . . . . ?
N1 C1 C11 C12 -61.0(2) . . . 4_565 ?
N1 C1 C11 C12 61.0(2) . . . . ?
C1 N1 C5 C4 0.000(0) . . . . ?
C1 N1 C5 C10 180.000(0) . . . . ?
C1 C2 C3 C4 0.000(1) . . . . ?
C1 C2 C3 C6 180.000(0) . . . . ?
C1 C11 C12 C13 -174.3(3) . . . . ?
C2 C1 C11 O1 0.000(1) . . . . ?
C2 C1 C11 C12 -119.0(2) . . . . ?
C2 C1 C11 C12 119.0(2) . . . 4_565 ?
C2 C3 C4 C5 0.000(0) . . . . ?
C2 C3 C4 C9 180.000(0) . . . . ?
C2 C3 C6 C7 180.000(0) . . . . ?
C3 C4 C5 N1 0.000(0) . . . . ?
C3 C4 C5 C10 180.000(0) . . . . ?
C3 C4 C9 C8 0.000(0) . . . . ?
C3 C6 C7 Br1 180.000(0) . . . . ?
C3 C6 C7 C8 0.000(0) . . . . ?
C4 C3 C6 C7 0.000(0) . . . . ?
C5 N1 C1 C2 0.000(1) . . . . ?
C5 N1 C1 C11 180.000(0) . . . . ?
C5 C4 C9 C8 180.000(0) . . . . ?
C6 C3 C4 C5 180.000(0) . . . . ?
C6 C3 C4 C9 0.000(0) . . . . ?
C6 C7 C8 C9 0.000(0) . . . . ?
C7 C8 C9 C4 0.000(0) . . . . ?
C9 C4 C5 N1 180.000(0) . . . . ?
C9 C4 C5 C10 0.000(0) . . . . ?
C11 C1 C2 C3 180.000(1) . . . . ?
C11 C12 C13 C14 54.7(4) . . . . ?
C12 C11 C12 C13 -52.4(5) 4_565 . . . ?
C12 C13 C14 C13 -55.6(5) . . . 4_565 ?

_olex2_submission_special_instructions 'No special instructions were received'
