# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_0423_auto
_database_code_depnum_ccdc_archive 'CCDC 2481110'
loop_
_audit_author_name
_audit_author_address
'cui zhiyang'
;CAU
China
;
_audit_update_record             
;
2025-08-16 deposited with the CCDC.	2026-02-05 downloaded from the CCDC.
;
_audit_creation_date             2025-04-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        1
_chemical_formula_moiety         'C25 H18 Br N O'
_chemical_formula_sum            'C25 H18 Br N O'
_chemical_formula_weight         428.31
_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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.9195(7)
_cell_length_b                   10.2361(6)
_cell_length_c                   10.9376(8)
_cell_angle_alpha                106.469(6)
_cell_angle_beta                 105.026(6)
_cell_angle_gamma                103.433(6)
_cell_volume                     970.91(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3235
_cell_measurement_temperature    293
_cell_measurement_theta_max      26.2640
_cell_measurement_theta_min      3.9480
_shelx_estimated_absorpt_T_max   0.901
_shelx_estimated_absorpt_T_min   0.883
_exptl_absorpt_coefficient_mu    2.132
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49328
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.465
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.837
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10043
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.428
_diffrn_reflns_theta_min         3.299
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0353
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.837
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -2.00  86.00   1.00    4.80    --   16.85  37.00  90.00   88
  2  ω    -10.00  42.00   1.00    4.80    --   16.85  77.00-180.00   52
  3  ω    -10.00  42.00   1.00    4.80    --   16.85  77.00 -60.00   52
  4  ω      0.00  84.00   1.00    4.80    --   16.85  57.00  90.00   84
  5  ω    -50.00  34.00   1.00    4.80    --   16.85 -57.00-150.00   84
  6  ω    -55.00  42.00   1.00    4.80    --   16.85 -19.00 -90.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0288030000
_diffrn_orient_matrix_UB_12      0.0384438000
_diffrn_orient_matrix_UB_13      0.0458986000
_diffrn_orient_matrix_UB_21      0.0058500000
_diffrn_orient_matrix_UB_22      0.0541102000
_diffrn_orient_matrix_UB_23      -0.0288250000
_diffrn_orient_matrix_UB_31      -0.0727216000
_diffrn_orient_matrix_UB_32      -0.0381358000
_diffrn_orient_matrix_UB_33      -0.0476229000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2886
_reflns_number_total             4509
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.775
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4509
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0507
_refine_ls_restrained_S_all      1.007
_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)+(0.0576P)²+0.2834P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1318
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C18(H18), C13(H13), C15(H15), C16(H16), C14(H14), C21(H21), C3(H3),
 C25(H25), C2(H2), C6(H6), C23(H23), C22(H22), C5(H5), C24(H24)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_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 0.33477(5) 0.20675(4) 0.89410(4) 0.0725(2) Uani 1 1 d . . . . .
N1 N 0.4624(3) 0.9055(2) 0.7889(2) 0.0353(6) Uani 1 1 d . . . . .
O1 O 0.0059(3) 0.8203(3) 0.5845(3) 0.0596(6) Uani 1 1 d . . . . .
C11 C 0.3865(3) 0.8106(3) 0.6647(3) 0.0322(6) Uani 1 1 d . . . . .
C12 C 0.6127(3) 0.9640(3) 0.8260(3) 0.0327(6) Uani 1 1 d . . . . .
C17 C 0.6881(3) 0.9246(3) 0.7359(3) 0.0337(6) Uani 1 1 d . . . . .
C8 C 0.2232(3) 0.7553(3) 0.6348(3) 0.0326(6) Uani 1 1 d . . . . .
C19 C 0.4513(3) 0.7665(3) 0.5650(3) 0.0332(6) Uani 1 1 d . . . . .
C7 C 0.1530(3) 0.6426(3) 0.6591(3) 0.0356(7) Uani 1 1 d . . . . .
H7 H 0.051779 0.625043 0.636771 0.043 Uiso 1 1 calc R . . . .
C20 C 0.3609(3) 0.6638(3) 0.4227(3) 0.0350(7) Uani 1 1 d . . . . .
C18 C 0.6018(3) 0.8242(3) 0.6031(3) 0.0364(7) Uani 1 1 d . . . . .
H18 H 0.647817 0.796852 0.540671 0.044 Uiso 1 1 calc R . . . .
C9 C 0.1322(3) 0.8413(3) 0.5857(3) 0.0394(7) Uani 1 1 d . . . . .
C4 C 0.2048(3) 0.5415(3) 0.7141(3) 0.0363(7) Uani 1 1 d . . . . .
C13 C 0.6928(4) 1.0645(3) 0.9592(3) 0.0432(7) Uani 1 1 d . . . . .
H13 H 0.643405 1.090671 1.018877 0.052 Uiso 1 1 calc R . . . .
C15 C 0.9177(4) 1.0835(3) 0.9124(3) 0.0466(8) Uani 1 1 d . . . . .
H15 H 1.020039 1.124046 0.942591 0.056 Uiso 1 1 calc R . . . .
C16 C 0.8437(3) 0.9864(3) 0.7827(3) 0.0414(7) Uani 1 1 d . . . . .
H16 H 0.895579 0.960804 0.725278 0.050 Uiso 1 1 calc R . . . .
C14 C 0.8420(4) 1.1230(3) 1.0006(3) 0.0469(8) Uani 1 1 d . . . . .
H14 H 0.894326 1.190096 1.088379 0.056 Uiso 1 1 calc R . . . .
C1 C 0.2815(4) 0.3416(3) 0.8199(3) 0.0473(8) Uani 1 1 d . . . . .
C21 C 0.2991(3) 0.5179(3) 0.3937(3) 0.0442(8) Uani 1 1 d . . . . .
H21 H 0.311138 0.482653 0.464043 0.053 Uiso 1 1 calc R . . . .
C3 C 0.0990(3) 0.4313(3) 0.7220(3) 0.0464(8) Uani 1 1 d . . . . .
H3 H 0.000141 0.424548 0.690948 0.056 Uiso 1 1 calc R . . . .
C25 C 0.3410(4) 0.7132(3) 0.3158(3) 0.0476(8) Uani 1 1 d . . . . .
H25 H 0.383548 0.810609 0.332938 0.057 Uiso 1 1 calc R . . . .
C2 C 0.1360(4) 0.3318(3) 0.7744(3) 0.0525(9) Uani 1 1 d . . . . .
H2 H 0.063338 0.259143 0.778837 0.063 Uiso 1 1 calc R . . . .
C6 C 0.3898(4) 0.4489(4) 0.8140(4) 0.0558(9) Uani 1 1 d . . . . .
H6 H 0.488374 0.454598 0.844885 0.067 Uiso 1 1 calc R . . . .
C23 C 0.1984(4) 0.4744(4) 0.1568(3) 0.0548(9) Uani 1 1 d . . . . .
H23 H 0.143557 0.411056 0.068024 0.066 Uiso 1 1 calc R . . . .
C22 C 0.2194(4) 0.4235(3) 0.2608(4) 0.0560(9) Uani 1 1 d . . . . .
H22 H 0.180036 0.325313 0.242283 0.067 Uiso 1 1 calc R . . . .
C5 C 0.3508(4) 0.5478(4) 0.7619(4) 0.0517(9) Uani 1 1 d . . . . .
H5 H 0.424322 0.620691 0.758568 0.062 Uiso 1 1 calc R . . . .
C24 C 0.2582(4) 0.6186(4) 0.1834(3) 0.0570(9) Uani 1 1 d . . . . .
H24 H 0.243271 0.653180 0.112677 0.068 Uiso 1 1 calc R . . . .
C10 C 0.2015(4) 0.9534(4) 0.5372(4) 0.0555(9) Uani 1 1 d . . . . .
H10A H 0.214397 0.907051 0.453504 0.083 Uiso 1 1 calc GR . . . .
H10B H 0.296007 1.014824 0.604455 0.083 Uiso 1 1 calc GR . . . .
H10C H 0.138645 1.010109 0.522478 0.083 Uiso 1 1 calc GR . . . .


_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 1.896(3) . ?
N1 C11 1.318(4) . ?
N1 C12 1.371(4) . ?
O1 C9 1.217(4) . ?
C11 C8 1.499(4) . ?
C11 C19 1.423(4) . ?
C12 C17 1.411(4) . ?
C12 C13 1.408(4) . ?
C17 C18 1.414(4) . ?
C17 C16 1.414(4) . ?
C8 C7 1.335(4) . ?
C8 C9 1.505(4) . ?
C19 C20 1.498(4) . ?
C19 C18 1.371(4) . ?
C7 C4 1.462(4) . ?
C20 C21 1.383(4) . ?
C20 C25 1.387(4) . ?
C9 C10 1.496(4) . ?
C4 C3 1.390(4) . ?
C4 C5 1.386(4) . ?
C13 C14 1.357(4) . ?
C15 C16 1.364(4) . ?
C15 C14 1.398(5) . ?
C1 C2 1.368(5) . ?
C1 C6 1.376(5) . ?
C21 C22 1.388(4) . ?
C3 C2 1.377(4) . ?
C25 C24 1.389(4) . ?
C6 C5 1.376(4) . ?
C23 C22 1.368(5) . ?
C23 C24 1.369(5) . ?

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 N1 C12 118.6(3) . . ?
N1 C11 C8 114.1(3) . . ?
N1 C11 C19 123.8(3) . . ?
C19 C11 C8 122.1(2) . . ?
N1 C12 C17 122.0(2) . . ?
N1 C12 C13 118.2(3) . . ?
C13 C12 C17 119.8(3) . . ?
C12 C17 C18 117.3(3) . . ?
C12 C17 C16 118.8(3) . . ?
C16 C17 C18 123.9(3) . . ?
C11 C8 C9 117.6(2) . . ?
C7 C8 C11 125.3(2) . . ?
C7 C8 C9 116.8(3) . . ?
C11 C19 C20 122.4(3) . . ?
C18 C19 C11 117.3(3) . . ?
C18 C19 C20 120.3(3) . . ?
C8 C7 C4 132.4(3) . . ?
C21 C20 C19 121.3(3) . . ?
C21 C20 C25 118.4(3) . . ?
C25 C20 C19 120.2(3) . . ?
C19 C18 C17 120.9(3) . . ?
O1 C9 C8 121.3(3) . . ?
O1 C9 C10 120.8(3) . . ?
C10 C9 C8 117.9(3) . . ?
C3 C4 C7 117.3(3) . . ?
C5 C4 C7 125.6(3) . . ?
C5 C4 C3 117.1(3) . . ?
C14 C13 C12 120.0(3) . . ?
C16 C15 C14 121.0(3) . . ?
C15 C16 C17 119.9(3) . . ?
C13 C14 C15 120.6(3) . . ?
C2 C1 Br1 119.5(2) . . ?
C2 C1 C6 120.9(3) . . ?
C6 C1 Br1 119.6(3) . . ?
C20 C21 C22 120.6(3) . . ?
C2 C3 C4 122.1(3) . . ?
C20 C25 C24 120.6(3) . . ?
C1 C2 C3 118.9(3) . . ?
C5 C6 C1 119.4(3) . . ?
C22 C23 C24 120.1(3) . . ?
C23 C22 C21 120.2(3) . . ?
C6 C5 C4 121.6(3) . . ?
C23 C24 C25 120.0(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.438
_oxdiff_exptl_absorpt_empirical_full_min 0.667
