# 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. 
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data_z1
_database_code_depnum_ccdc_archive 'CCDC 2417115'
loop_
_audit_author_name
_audit_author_address
'Zhi-Qiang Zhu'
;East China University of Technology
China
;
_audit_update_record             
;
2025-01-15 deposited with the CCDC.	2025-05-12 downloaded from the CCDC.
;
_audit_creation_date             2024-12-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H19 Br N4 O2'
_chemical_formula_sum            'C21 H19 Br N4 O2'
_chemical_formula_weight         439.31
_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           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                   13.6693(11)
_cell_length_b                   14.0976(9)
_cell_length_c                   11.4593(7)
_cell_angle_alpha                90
_cell_angle_beta                 113.319(8)
_cell_angle_gamma                90
_cell_volume                     2027.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2732
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.1230
_cell_measurement_theta_min      3.8250
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.051
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_unetI/netI     0.0887
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.862
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13361
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.862
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.397
_diffrn_reflns_theta_min         3.315
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.862
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2165
_reflns_number_total             4826
_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  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4826
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1601
_refine_ls_R_factor_gt           0.0577
_refine_ls_restrained_S_all      1.008
_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)+(0.0440P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1367
_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 Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C15(H15A,H15B), C5(H5A,H5B), C4(H4A,H4B), C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C17(H17), C18(H18), C21(H21), C20(H20), C10(H10), C13(H13),
 C12(H12), C11(H11)
;
_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
O2 O 0.13307(19) 0.4625(2) 0.4956(2) 0.0604(7) Uani 1 1 d . . . . .
O1 O 0.46609(19) 0.5844(2) 0.6052(2) 0.0663(8) Uani 1 1 d . . . . .
N1 N 0.3019(2) 0.5189(2) 0.5485(2) 0.0440(7) Uani 1 1 d . . . . .
N2 N 0.2167(2) 0.5344(2) 0.6874(2) 0.0474(8) Uani 1 1 d . . . . .
N3 N 0.3052(2) 0.5722(2) 0.7800(2) 0.0496(8) Uani 1 1 d . . . . .
C3 C 0.2114(3) 0.5020(3) 0.5720(3) 0.0482(10) Uani 1 1 d . . . . .
C16 C 0.2677(3) 0.5496(3) 0.3207(3) 0.0463(9) Uani 1 1 d . . . . .
C9 C 0.1358(2) 0.4378(3) 0.8059(3) 0.0461(9) Uani 1 1 d . . . . .
C1 C 0.3899(3) 0.5645(3) 0.6309(3) 0.0482(9) Uani 1 1 d . . . . .
C2 C 0.3871(3) 0.5871(3) 0.7550(3) 0.0476(9) Uani 1 1 d . . . . .
C19 C 0.2004(3) 0.6741(3) 0.1184(3) 0.0526(10) Uani 1 1 d . . . . .
C8 C 0.1253(3) 0.5229(3) 0.7229(3) 0.0523(10) Uani 1 1 d . . . . .
H8A H 0.060889 0.516797 0.646337 0.063 Uiso 1 1 calc R U . . .
H8B H 0.118364 0.579373 0.767425 0.063 Uiso 1 1 calc R U . . .
N4 N 0.6049(3) 0.6672(3) 1.3082(3) 0.0806(12) Uani 1 1 d . . . . .
C15 C 0.3053(3) 0.4795(3) 0.4303(3) 0.0541(10) Uani 1 1 d . . . . .
H15A H 0.260831 0.423268 0.405962 0.065 Uiso 1 1 calc R U . . .
H15B H 0.377748 0.460477 0.446675 0.065 Uiso 1 1 calc R U . . .
C14 C 0.1076(3) 0.3489(3) 0.7540(3) 0.0590(11) Uani 1 1 d . . . . .
H14 H 0.080808 0.341782 0.666239 0.071 Uiso 1 1 calc R U . . .
C17 C 0.3398(3) 0.5992(3) 0.2890(3) 0.0575(11) Uani 1 1 d . . . . .
H17 H 0.412204 0.590532 0.336457 0.069 Uiso 1 1 calc R U . . .
C18 C 0.3068(3) 0.6623(3) 0.1873(3) 0.0617(11) Uani 1 1 d . . . . .
H18 H 0.356459 0.695754 0.166802 0.074 Uiso 1 1 calc R U . . .
C21 C 0.1603(3) 0.5623(3) 0.2491(3) 0.0607(12) Uani 1 1 d . . . . .
H21 H 0.110418 0.528364 0.268596 0.073 Uiso 1 1 calc R U . . .
C7 C 0.5965(3) 0.6763(3) 1.2075(4) 0.0601(11) Uani 1 1 d . . . . .
C5 C 0.4816(3) 0.6436(3) 0.9823(3) 0.0626(12) Uani 1 1 d . . . . .
H5A H 0.468708 0.583681 1.015458 0.075 Uiso 1 1 calc R U . . .
H5B H 0.422739 0.685742 0.972494 0.075 Uiso 1 1 calc R U . . .
C20 C 0.1267(3) 0.6258(3) 0.1479(3) 0.0643(12) Uani 1 1 d . . . . .
H20 H 0.054341 0.635194 0.100640 0.077 Uiso 1 1 calc R U . . .
C4 C 0.4860(3) 0.6274(3) 0.8552(3) 0.0615(11) Uani 1 1 d . . . . .
H4A H 0.501580 0.687370 0.824793 0.074 Uiso 1 1 calc R U . . .
H4B H 0.544740 0.584743 0.866423 0.074 Uiso 1 1 calc R U . . .
C10 C 0.1754(3) 0.4460(3) 0.9369(3) 0.0622(11) Uani 1 1 d . . . . .
H10 H 0.195108 0.505263 0.974487 0.075 Uiso 1 1 calc R U . . .
C13 C 0.1182(3) 0.2699(3) 0.8298(5) 0.0732(13) Uani 1 1 d . . . . .
H13 H 0.098253 0.210427 0.792913 0.088 Uiso 1 1 calc R U . . .
C12 C 0.1583(3) 0.2796(4) 0.9591(4) 0.0738(14) Uani 1 1 d . . . . .
H12 H 0.166442 0.226385 1.010156 0.089 Uiso 1 1 calc R U . . .
C6 C 0.5845(3) 0.6866(4) 1.0761(3) 0.0760(13) Uani 1 1 d . . . . .
H6A H 0.644245 0.656143 1.065802 0.091 Uiso 1 1 calc R U . . .
H6B H 0.586195 0.753425 1.057045 0.091 Uiso 1 1 calc R U . . .
C11 C 0.1861(3) 0.3664(4) 1.0133(4) 0.0761(14) Uani 1 1 d . . . . .
H11 H 0.212325 0.372788 1.101151 0.091 Uiso 1 1 calc R U . . .
Br1 Br 0.15558(4) 0.75584(3) -0.02512(4) 0.0861(2) 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
O2 C3 1.217(4) . ?
O1 C1 1.223(4) . ?
N1 C3 1.387(4) . ?
N1 C1 1.361(4) . ?
N1 C15 1.482(4) . ?
N2 N3 1.363(3) . ?
N2 C3 1.373(4) . ?
N2 C8 1.469(4) . ?
N3 C2 1.279(4) . ?
C16 C15 1.519(5) . ?
C16 C17 1.369(5) . ?
C16 C21 1.380(4) . ?
C9 C8 1.502(5) . ?
C9 C14 1.375(5) . ?
C9 C10 1.384(4) . ?
C1 C2 1.472(5) . ?
C2 C4 1.496(5) . ?
C19 C18 1.363(5) . ?
C19 C20 1.366(5) . ?
C19 Br1 1.900(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
N4 C7 1.121(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C14 H14 0.9300 . ?
C14 C13 1.384(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.392(5) . ?
C18 H18 0.9300 . ?
C21 H21 0.9300 . ?
C21 C20 1.391(5) . ?
C7 C6 1.456(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C4 1.499(4) . ?
C5 C6 1.518(5) . ?
C20 H20 0.9300 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C10 H10 0.9300 . ?
C10 C11 1.394(6) . ?
C13 H13 0.9300 . ?
C13 C12 1.368(6) . ?
C12 H12 0.9300 . ?
C12 C11 1.357(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C11 H11 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 N1 C15 117.8(3) . . ?
C1 N1 C3 123.9(3) . . ?
C1 N1 C15 118.2(3) . . ?
N3 N2 C3 125.0(3) . . ?
N3 N2 C8 114.6(3) . . ?
C3 N2 C8 120.2(3) . . ?
C2 N3 N2 118.4(3) . . ?
O2 C3 N1 122.5(3) . . ?
O2 C3 N2 122.8(3) . . ?
N2 C3 N1 114.7(3) . . ?
C17 C16 C15 120.5(3) . . ?
C17 C16 C21 118.9(3) . . ?
C21 C16 C15 120.5(3) . . ?
C14 C9 C8 120.9(3) . . ?
C14 C9 C10 117.8(4) . . ?
C10 C9 C8 121.3(4) . . ?
O1 C1 N1 123.0(3) . . ?
O1 C1 C2 122.2(3) . . ?
N1 C1 C2 114.8(3) . . ?
N3 C2 C1 122.7(3) . . ?
N3 C2 C4 119.7(3) . . ?
C1 C2 C4 117.6(3) . . ?
C18 C19 C20 121.2(4) . . ?
C18 C19 Br1 118.7(3) . . ?
C20 C19 Br1 120.1(3) . . ?
N2 C8 C9 112.6(3) . . ?
N2 C8 H8A 109.1 . . ?
N2 C8 H8B 109.1 . . ?
C9 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
N1 C15 C16 112.9(3) . . ?
N1 C15 H15A 109.0 . . ?
N1 C15 H15B 109.0 . . ?
C16 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C9 C14 H14 119.3 . . ?
C9 C14 C13 121.4(4) . . ?
C13 C14 H14 119.3 . . ?
C16 C17 H17 119.3 . . ?
C16 C17 C18 121.3(3) . . ?
C18 C17 H17 119.3 . . ?
C19 C18 C17 118.7(4) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
C16 C21 H21 119.9 . . ?
C16 C21 C20 120.1(4) . . ?
C20 C21 H21 119.9 . . ?
N4 C7 C6 178.9(5) . . ?
H5A C5 H5B 108.0 . . ?
C4 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
C4 C5 C6 111.5(3) . . ?
C6 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C19 C20 C21 119.7(3) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C2 C4 C5 115.6(3) . . ?
C2 C4 H4A 108.4 . . ?
C2 C4 H4B 108.4 . . ?
C5 C4 H4A 108.4 . . ?
C5 C4 H4B 108.4 . . ?
H4A C4 H4B 107.4 . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.8(4) . . ?
C11 C10 H10 119.6 . . ?
C14 C13 H13 120.1 . . ?
C12 C13 C14 119.8(4) . . ?
C12 C13 H13 120.1 . . ?
C13 C12 H12 119.8 . . ?
C11 C12 C13 120.3(4) . . ?
C11 C12 H12 119.8 . . ?
C7 C6 C5 112.7(3) . . ?
C7 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
C5 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.9(4) . . ?
C12 C11 H11 120.1 . . ?

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 C1 C2 N3 175.3(4) . . . . ?
O1 C1 C2 C4 -5.9(6) . . . . ?
N1 C1 C2 N3 -5.5(5) . . . . ?
N1 C1 C2 C4 173.3(3) . . . . ?
N2 N3 C2 C1 -0.5(5) . . . . ?
N2 N3 C2 C4 -179.3(3) . . . . ?
N3 N2 C3 O2 174.5(3) . . . . ?
N3 N2 C3 N1 -6.3(5) . . . . ?
N3 N2 C8 C9 -77.9(4) . . . . ?
N3 C2 C4 C5 2.5(5) . . . . ?
C3 N1 C1 O1 -174.9(3) . . . . ?
C3 N1 C1 C2 5.9(5) . . . . ?
C3 N1 C15 C16 93.8(4) . . . . ?
C3 N2 N3 C2 6.8(5) . . . . ?
C3 N2 C8 C9 97.6(4) . . . . ?
C16 C17 C18 C19 -0.2(6) . . . . ?
C16 C21 C20 C19 1.2(6) . . . . ?
C9 C14 C13 C12 -0.4(6) . . . . ?
C9 C10 C11 C12 0.5(6) . . . . ?
C1 N1 C3 O2 178.7(3) . . . . ?
C1 N1 C3 N2 -0.5(5) . . . . ?
C1 N1 C15 C16 -90.0(4) . . . . ?
C1 C2 C4 C5 -176.3(3) . . . . ?
C8 N2 N3 C2 -177.9(3) . . . . ?
C8 N2 C3 O2 -0.6(5) . . . . ?
C8 N2 C3 N1 178.7(3) . . . . ?
C8 C9 C14 C13 179.2(3) . . . . ?
C8 C9 C10 C11 -179.2(3) . . . . ?
C15 N1 C3 O2 -5.3(5) . . . . ?
C15 N1 C3 N2 175.4(3) . . . . ?
C15 N1 C1 O1 9.2(5) . . . . ?
C15 N1 C1 C2 -170.1(3) . . . . ?
C15 C16 C17 C18 178.7(3) . . . . ?
C15 C16 C21 C20 -179.2(3) . . . . ?
C14 C9 C8 N2 -83.2(4) . . . . ?
C14 C9 C10 C11 0.0(5) . . . . ?
C14 C13 C12 C11 0.9(6) . . . . ?
C17 C16 C15 N1 100.1(4) . . . . ?
C17 C16 C21 C20 -1.0(6) . . . . ?
C18 C19 C20 C21 -0.8(6) . . . . ?
C21 C16 C15 N1 -81.7(4) . . . . ?
C21 C16 C17 C18 0.5(6) . . . . ?
C20 C19 C18 C17 0.3(6) . . . . ?
C4 C5 C6 C7 -162.2(4) . . . . ?
C10 C9 C8 N2 95.9(4) . . . . ?
C10 C9 C14 C13 0.0(5) . . . . ?
C13 C12 C11 C10 -1.0(6) . . . . ?
C6 C5 C4 C2 -178.7(4) . . . . ?
Br1 C19 C18 C17 -177.1(3) . . . . ?
Br1 C19 C20 C21 176.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
