# 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_yl20251121a_0ma
_database_code_depnum_ccdc_archive 'CCDC 2517520'
loop_
_audit_author_name
_audit_author_address
ylyfk
;qingdao university of science and technology
China
;
_audit_update_record             
;
2025-12-19 deposited with the CCDC.	2026-05-28 downloaded from the CCDC.
;
_audit_creation_date             2025-11-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H15 Br N2'
_chemical_formula_sum            'C21 H15 Br N2'
_chemical_formula_weight         375.26
_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'

_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                   13.6554(11)
_cell_length_b                   14.8377(13)
_cell_length_c                   8.5743(6)
_cell_angle_alpha                90
_cell_angle_beta                 106.457(3)
_cell_angle_gamma                90
_cell_volume                     1666.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4994
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.300
_cell_measurement_theta_min      2.745
_shelx_estimated_absorpt_T_max   0.790
_shelx_estimated_absorpt_T_min   0.740
_exptl_absorpt_coefficient_mu    2.470
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6376
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0903 before and 0.0663 after correction.
The Ratio of minimum to maximum transmission is 0.8556.
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    1.496
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            18291
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.361
_diffrn_reflns_theta_min         2.746
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_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                2608
_reflns_number_total             3055
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3055
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0295
_refine_ls_restrained_S_all      1.062
_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)+(0.0307P)²+0.4392P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0680
_refine_ls_wR_factor_ref         0.0715
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C1(H1A), C5(H5), C2(H2), C21(H21), C12(H12), C8(H8), C14(H14),
  C17(H17), C15(H15), C13(H13), C20(H20), C18(H18), C19(H19)
;
_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 0.02461(2) 0.09749(2) 0.13988(3) 0.03849(11) Uani 1 1 d . . . . .
N2 N 0.48055(13) 0.34211(11) 0.46534(19) 0.0208(4) Uani 1 1 d . . . . .
N1 N 0.41221(13) 0.23914(12) 0.6158(2) 0.0256(4) Uani 1 1 d . . . . .
H1 H 0.423185 0.215080 0.710494 0.031 Uiso 1 1 calc R U . . .
C7 C 0.48632(15) 0.29945(14) 0.6026(2) 0.0214(4) Uani 1 1 d . . . . .
C10 C 0.64658(16) 0.41345(13) 0.6024(3) 0.0217(5) Uani 1 1 d . . . . .
C11 C 0.55975(16) 0.40089(14) 0.4665(3) 0.0225(5) Uani 1 1 d . . . . .
C3 C 0.14305(16) 0.14532(15) 0.2917(3) 0.0257(5) Uani 1 1 d . . . . .
C4 C 0.19276(17) 0.09452(15) 0.4259(3) 0.0269(5) Uani 1 1 d . . . . .
H4 H 0.166168 0.039411 0.445887 0.032 Uiso 1 1 calc R U . . .
C6 C 0.32248(15) 0.21017(14) 0.5028(2) 0.0221(4) Uani 1 1 d . . . . .
C1 C 0.26975(16) 0.26070(15) 0.3691(2) 0.0254(5) Uani 1 1 d . . . . .
H1A H 0.294404 0.316971 0.350766 0.030 Uiso 1 1 calc R U . . .
C9 C 0.65161(16) 0.36148(14) 0.7467(3) 0.0228(4) Uani 1 1 d . . . . .
C5 C 0.28238(16) 0.12678(15) 0.5299(3) 0.0248(5) Uani 1 1 d . . . . .
H5 H 0.316724 0.092511 0.619534 0.030 Uiso 1 1 calc R U . . .
C16 C 0.74020(16) 0.36202(14) 0.8937(3) 0.0257(5) Uani 1 1 d . . . . .
C2 C 0.18056(16) 0.22788(15) 0.2625(3) 0.0284(5) Uani 1 1 d . . . . .
H2 H 0.146274 0.261427 0.171861 0.034 Uiso 1 1 calc R U . . .
C21 C 0.72590(18) 0.36472(15) 1.0480(3) 0.0297(5) Uani 1 1 d . . . . .
H21 H 0.660221 0.370401 1.058465 0.036 Uiso 1 1 calc R U . . .
C12 C 0.55311(17) 0.45026(15) 0.3232(3) 0.0275(5) Uani 1 1 d . . . . .
H12 H 0.496912 0.442125 0.233050 0.033 Uiso 1 1 calc R U . . .
C8 C 0.57044(16) 0.30791(14) 0.7443(2) 0.0235(5) Uani 1 1 d . . . . .
H8 H 0.569938 0.276073 0.837518 0.028 Uiso 1 1 calc R U . . .
C14 C 0.71234(18) 0.52378(16) 0.4489(3) 0.0324(5) Uani 1 1 d . . . . .
H14 H 0.762585 0.564831 0.442745 0.039 Uiso 1 1 calc R U . . .
C17 C 0.83975(17) 0.35342(16) 0.8825(3) 0.0309(5) Uani 1 1 d . . . . .
H17 H 0.851196 0.351006 0.780717 0.037 Uiso 1 1 calc R U . . .
C15 C 0.72119(17) 0.47687(15) 0.5899(3) 0.0281(5) Uani 1 1 d . . . . .
H15 H 0.777443 0.486978 0.679110 0.034 Uiso 1 1 calc R U . . .
C13 C 0.62787(18) 0.50992(15) 0.3144(3) 0.0312(5) Uani 1 1 d . . . . .
H13 H 0.622346 0.541336 0.218423 0.037 Uiso 1 1 calc R U . . .
C20 C 0.8080(2) 0.35908(16) 1.1861(3) 0.0377(6) Uani 1 1 d . . . . .
H20 H 0.797127 0.360721 1.288349 0.045 Uiso 1 1 calc R U . . .
C18 C 0.92137(19) 0.34846(17) 1.0206(3) 0.0399(6) Uani 1 1 d . . . . .
H18 H 0.987318 0.343357 1.011090 0.048 Uiso 1 1 calc R U . . .
C19 C 0.9059(2) 0.35101(17) 1.1725(3) 0.0427(6) Uani 1 1 d . . . . .
H19 H 0.961158 0.347326 1.265302 0.051 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 C3 1.903(2) . ?
N2 C7 1.319(3) . ?
N2 C11 1.387(3) . ?
N1 H1 0.8600 . ?
N1 C7 1.379(3) . ?
N1 C6 1.397(3) . ?
C7 C8 1.421(3) . ?
C10 C11 1.420(3) . ?
C10 C9 1.443(3) . ?
C10 C15 1.413(3) . ?
C11 C12 1.411(3) . ?
C3 C4 1.383(3) . ?
C3 C2 1.378(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.380(3) . ?
C6 C1 1.388(3) . ?
C6 C5 1.399(3) . ?
C1 H1A 0.9300 . ?
C1 C2 1.387(3) . ?
C9 C16 1.479(3) . ?
C9 C8 1.359(3) . ?
C5 H5 0.9300 . ?
C16 C21 1.392(3) . ?
C16 C17 1.395(3) . ?
C2 H2 0.9300 . ?
C21 H21 0.9300 . ?
C21 C20 1.383(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.369(3) . ?
C8 H8 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.371(3) . ?
C14 C13 1.396(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.379(3) . ?
C15 H15 0.9300 . ?
C13 H13 0.9300 . ?
C20 H20 0.9300 . ?
C20 C19 1.381(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.378(4) . ?
C19 H19 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
C7 N2 C11 116.49(17) . . ?
C7 N1 H1 114.3 . . ?
C7 N1 C6 131.47(17) . . ?
C6 N1 H1 114.3 . . ?
N2 C7 N1 121.66(19) . . ?
N2 C7 C8 123.36(18) . . ?
N1 C7 C8 114.91(18) . . ?
C11 C10 C9 117.36(18) . . ?
C15 C10 C11 118.49(19) . . ?
C15 C10 C9 124.1(2) . . ?
N2 C11 C10 123.79(18) . . ?
N2 C11 C12 117.56(19) . . ?
C12 C11 C10 118.65(19) . . ?
C4 C3 Br1 119.20(17) . . ?
C2 C3 Br1 119.68(17) . . ?
C2 C3 C4 121.1(2) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 C3 119.0(2) . . ?
C5 C4 H4 120.5 . . ?
N1 C6 C5 117.67(19) . . ?
C1 C6 N1 123.67(19) . . ?
C1 C6 C5 118.63(19) . . ?
C6 C1 H1A 119.8 . . ?
C2 C1 C6 120.5(2) . . ?
C2 C1 H1A 119.8 . . ?
C10 C9 C16 123.81(19) . . ?
C8 C9 C10 117.34(19) . . ?
C8 C9 C16 118.84(19) . . ?
C4 C5 C6 121.1(2) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C21 C16 C9 120.60(19) . . ?
C21 C16 C17 118.0(2) . . ?
C17 C16 C9 121.23(19) . . ?
C3 C2 C1 119.7(2) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C16 C21 H21 119.5 . . ?
C20 C21 C16 120.9(2) . . ?
C20 C21 H21 119.5 . . ?
C11 C12 H12 119.4 . . ?
C13 C12 C11 121.2(2) . . ?
C13 C12 H12 119.4 . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.50(19) . . ?
C9 C8 H8 119.3 . . ?
C15 C14 H14 120.0 . . ?
C15 C14 C13 120.0(2) . . ?
C13 C14 H14 120.0 . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.8(2) . . ?
C18 C17 H17 119.6 . . ?
C10 C15 H15 119.3 . . ?
C14 C15 C10 121.3(2) . . ?
C14 C15 H15 119.3 . . ?
C12 C13 C14 120.3(2) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C21 C20 H20 119.9 . . ?
C19 C20 C21 120.2(2) . . ?
C19 C20 H20 119.9 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.5(2) . . ?
C19 C18 H18 119.8 . . ?
C20 C19 H19 120.2 . . ?
C18 C19 C20 119.6(2) . . ?
C18 C19 H19 120.2 . . ?

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 C3 C4 C5 175.72(15) . . . . ?
Br1 C3 C2 C1 -176.84(15) . . . . ?
N2 C7 C8 C9 -0.1(3) . . . . ?
N2 C11 C12 C13 179.77(19) . . . . ?
N1 C7 C8 C9 176.75(19) . . . . ?
N1 C6 C1 C2 -179.47(19) . . . . ?
N1 C6 C5 C4 178.45(18) . . . . ?
C7 N2 C11 C10 3.1(3) . . . . ?
C7 N2 C11 C12 -177.31(18) . . . . ?
C7 N1 C6 C1 -25.2(3) . . . . ?
C7 N1 C6 C5 157.0(2) . . . . ?
C10 C11 C12 C13 -0.6(3) . . . . ?
C10 C9 C16 C21 138.0(2) . . . . ?
C10 C9 C16 C17 -46.6(3) . . . . ?
C10 C9 C8 C7 3.4(3) . . . . ?
C11 N2 C7 N1 -179.77(18) . . . . ?
C11 N2 C7 C8 -3.1(3) . . . . ?
C11 C10 C9 C16 175.40(19) . . . . ?
C11 C10 C9 C8 -3.3(3) . . . . ?
C11 C10 C15 C14 -1.8(3) . . . . ?
C11 C12 C13 C14 -0.6(3) . . . . ?
C3 C4 C5 C6 1.0(3) . . . . ?
C4 C3 C2 C1 0.2(3) . . . . ?
C6 N1 C7 N2 0.1(3) . . . . ?
C6 N1 C7 C8 -176.8(2) . . . . ?
C6 C1 C2 C3 1.3(3) . . . . ?
C1 C6 C5 C4 0.5(3) . . . . ?
C9 C10 C11 N2 0.1(3) . . . . ?
C9 C10 C11 C12 -179.49(19) . . . . ?
C9 C10 C15 C14 179.6(2) . . . . ?
C9 C16 C21 C20 175.6(2) . . . . ?
C9 C16 C17 C18 -176.0(2) . . . . ?
C5 C6 C1 C2 -1.6(3) . . . . ?
C16 C9 C8 C7 -175.38(19) . . . . ?
C16 C21 C20 C19 0.3(4) . . . . ?
C16 C17 C18 C19 0.7(4) . . . . ?
C2 C3 C4 C5 -1.3(3) . . . . ?
C21 C16 C17 C18 -0.5(3) . . . . ?
C21 C20 C19 C18 -0.1(4) . . . . ?
C8 C9 C16 C21 -43.4(3) . . . . ?
C8 C9 C16 C17 132.0(2) . . . . ?
C17 C16 C21 C20 0.0(3) . . . . ?
C17 C18 C19 C20 -0.3(4) . . . . ?
C15 C10 C11 N2 -178.60(18) . . . . ?
C15 C10 C11 C12 1.8(3) . . . . ?
C15 C10 C9 C16 -6.0(3) . . . . ?
C15 C10 C9 C8 175.33(19) . . . . ?
C15 C14 C13 C12 0.7(3) . . . . ?
C13 C14 C15 C10 0.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
