# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_11
_database_code_depnum_ccdc_archive 'CCDC 2512208'
loop_
_audit_author_name
_audit_author_address
'Zhao Zhifei'
;Shihezi University
China
;
_audit_update_record             
;
2025-12-01 deposited with the CCDC.	2026-02-05 downloaded from the CCDC.
;
_audit_creation_date             2025-10-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H16 Br N'
_chemical_formula_sum            'C18 H16 Br N'
_chemical_formula_weight         326.23
_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 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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                   5.8713(5)
_cell_length_b                   9.6203(9)
_cell_length_c                   13.4415(12)
_cell_angle_alpha                90.831(3)
_cell_angle_beta                 95.528(3)
_cell_angle_gamma                95.559(3)
_cell_volume                     751.92(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7745
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      72.20
_cell_measurement_theta_min      4.62
_shelx_estimated_absorpt_T_max   0.517
_shelx_estimated_absorpt_T_min   0.465
_exptl_absorpt_coefficient_mu    3.618
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.4430
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1163 before and 0.0538 after correction.
The Ratio of minimum to maximum transmission is 0.5878.
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    1.441
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8691
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.228
_diffrn_reflns_theta_min         4.619
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2811
_reflns_number_total             2884
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2884
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0316
_refine_ls_restrained_S_all      1.117
_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)+(0.0410P)²+0.3598P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.0852
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
2.d :
 C12(H12)
;
_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 0.02332(4) -0.32615(2) 0.95445(2) 0.03971(12) Uani 1 1 d . . . . .
N1 N 0.5759(3) 0.49851(17) 0.68103(13) 0.0293(4) Uani 1 1 d . . . . .
H1 H 0.427342 0.472201 0.673243 0.035 Uiso 1 1 calc R U . . .
C1 C 0.4240(3) 0.04941(19) 0.80677(14) 0.0244(4) Uani 1 1 d . . . . .
C2 C 0.5026(3) -0.0838(2) 0.80766(15) 0.0268(4) Uani 1 1 d . . . . .
H2 H 0.639038 -0.097445 0.777697 0.032 Uiso 1 1 calc R U . . .
C3 C 0.3870(4) -0.1959(2) 0.85092(15) 0.0302(4) Uani 1 1 d . . . . .
H3 H 0.444243 -0.284917 0.851892 0.036 Uiso 1 1 calc R U . . .
C4 C 0.1853(3) -0.1754(2) 0.89292(14) 0.0290(4) Uani 1 1 d . . . . .
C5 C 0.0950(3) -0.0477(2) 0.88820(15) 0.0299(4) Uani 1 1 d . . . . .
H5 H -0.047196 -0.036536 0.914170 0.036 Uiso 1 1 calc R U . . .
C6 C 0.2134(3) 0.0635(2) 0.84540(15) 0.0283(4) Uani 1 1 d . . . . .
H6 H 0.151214 0.151010 0.842053 0.034 Uiso 1 1 calc R U . . .
C7 C 0.5625(3) 0.1647(2) 0.76384(14) 0.0256(4) Uani 1 1 d . . . . .
H7 H 0.651964 0.139485 0.712395 0.031 Uiso 1 1 calc R U . . .
C8 C 0.5781(3) 0.3012(2) 0.78842(13) 0.0248(4) Uani 1 1 d . . . . .
C9 C 0.4547(4) 0.3663(2) 0.86771(16) 0.0333(4) Uani 1 1 d . . . . .
H9A H 0.304514 0.389982 0.838266 0.050 Uiso 1 1 calc R U . . .
H9B H 0.546340 0.451274 0.894986 0.050 Uiso 1 1 calc R U . . .
H9C H 0.432992 0.299969 0.921444 0.050 Uiso 1 1 calc R U . . .
C10 C 0.7283(3) 0.40799(19) 0.73503(14) 0.0251(4) Uani 1 1 d . . . . .
H10 H 0.825907 0.467112 0.787704 0.030 Uiso 1 1 calc R U . . .
C11 C 0.8851(3) 0.3484(2) 0.67012(15) 0.0284(4) Uani 1 1 d . . . . .
C12 C 1.0131(4) 0.3066(2) 0.61595(18) 0.0387(5) Uani 1 1 d . . . . .
H12 H 1.115414 0.273102 0.572663 0.046 Uiso 1 1 calc R U . . .
C13 C 0.6558(3) 0.62454(19) 0.64142(14) 0.0240(4) Uani 1 1 d . . . . .
C14 C 0.5042(3) 0.6914(2) 0.57532(15) 0.0292(4) Uani 1 1 d . . . . .
H14 H 0.356300 0.646075 0.553840 0.035 Uiso 1 1 calc R U . . .
C15 C 0.5689(4) 0.8225(2) 0.54145(16) 0.0332(4) Uani 1 1 d . . . . .
H15 H 0.464096 0.866985 0.497243 0.040 Uiso 1 1 calc R U . . .
C16 C 0.7852(4) 0.8908(2) 0.57096(16) 0.0315(4) Uani 1 1 d . . . . .
H16 H 0.826987 0.982147 0.548684 0.038 Uiso 1 1 calc R U . . .
C17 C 0.9386(3) 0.8234(2) 0.63338(15) 0.0280(4) Uani 1 1 d . . . . .
H17 H 1.087765 0.868279 0.653014 0.034 Uiso 1 1 calc R U . . .
C18 C 0.8766(3) 0.6908(2) 0.66758(14) 0.0256(4) Uani 1 1 d . . . . .
H18 H 0.984891 0.644799 0.708970 0.031 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 C4 1.900(2) . ?
N1 H1 0.8800 . ?
N1 C10 1.460(2) . ?
N1 C13 1.389(3) . ?
C1 C2 1.404(3) . ?
C1 C6 1.404(3) . ?
C1 C7 1.469(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.383(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(3) . ?
C4 C5 1.385(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.381(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C7 C8 1.342(3) . ?
C8 C9 1.507(3) . ?
C8 C10 1.522(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10 1.0000 . ?
C10 C11 1.476(3) . ?
C11 C12 1.189(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.404(3) . ?
C13 C18 1.398(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.378(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.391(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.385(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.389(3) . ?
C18 H18 0.9500 . ?

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
C10 N1 H1 118.7 . . ?
C13 N1 H1 118.7 . . ?
C13 N1 C10 122.64(16) . . ?
C2 C1 C6 117.47(18) . . ?
C2 C1 C7 118.63(17) . . ?
C6 C1 C7 123.89(17) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 C1 121.88(18) . . ?
C3 C2 H2 119.1 . . ?
C2 C3 H3 120.7 . . ?
C2 C3 C4 118.58(18) . . ?
C4 C3 H3 120.7 . . ?
C3 C4 Br1 119.87(16) . . ?
C5 C4 Br1 118.88(15) . . ?
C5 C4 C3 121.22(19) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.41(18) . . ?
C6 C5 H5 120.3 . . ?
C1 C6 H6 119.4 . . ?
C5 C6 C1 121.23(18) . . ?
C5 C6 H6 119.4 . . ?
C1 C7 H7 116.0 . . ?
C8 C7 C1 127.92(18) . . ?
C8 C7 H7 116.0 . . ?
C7 C8 C9 125.90(18) . . ?
C7 C8 C10 121.21(17) . . ?
C9 C8 C10 112.88(16) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 C8 107.28(15) . . ?
N1 C10 H10 107.2 . . ?
N1 C10 C11 112.45(16) . . ?
C8 C10 H10 107.2 . . ?
C11 C10 C8 115.05(16) . . ?
C11 C10 H10 107.2 . . ?
C12 C11 C10 176.9(2) . . ?
C11 C12 H12 180.0 . . ?
N1 C13 C14 118.32(17) . . ?
N1 C13 C18 123.13(17) . . ?
C18 C13 C14 118.49(18) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.33(19) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 119.5 . . ?
C14 C15 C16 121.05(19) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 120.5 . . ?
C17 C16 C15 118.92(19) . . ?
C17 C16 H16 120.5 . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.72(18) . . ?
C18 C17 H17 119.6 . . ?
C13 C18 H18 119.8 . . ?
C17 C18 C13 120.38(17) . . ?
C17 C18 H18 119.8 . . ?

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
Br1 C4 C5 C6 178.75(14) . . . . ?
N1 C13 C14 C15 173.99(18) . . . . ?
N1 C13 C18 C17 -173.36(17) . . . . ?
C1 C2 C3 C4 1.2(3) . . . . ?
C1 C7 C8 C9 0.4(3) . . . . ?
C1 C7 C8 C10 -179.10(17) . . . . ?
C2 C1 C6 C5 3.8(3) . . . . ?
C2 C1 C7 C8 -150.8(2) . . . . ?
C2 C3 C4 Br1 -179.28(14) . . . . ?
C2 C3 C4 C5 2.8(3) . . . . ?
C3 C4 C5 C6 -3.3(3) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
C6 C1 C2 C3 -4.4(3) . . . . ?
C6 C1 C7 C8 30.6(3) . . . . ?
C7 C1 C2 C3 176.98(17) . . . . ?
C7 C1 C6 C5 -177.59(18) . . . . ?
C7 C8 C10 N1 114.81(19) . . . . ?
C7 C8 C10 C11 -11.1(3) . . . . ?
C9 C8 C10 N1 -64.8(2) . . . . ?
C9 C8 C10 C11 169.28(17) . . . . ?
C10 N1 C13 C14 168.33(17) . . . . ?
C10 N1 C13 C18 -14.5(3) . . . . ?
C13 N1 C10 C8 166.15(16) . . . . ?
C13 N1 C10 C11 -66.4(2) . . . . ?
C13 C14 C15 C16 0.6(3) . . . . ?
C14 C13 C18 C17 3.8(3) . . . . ?
C14 C15 C16 C17 1.7(3) . . . . ?
C15 C16 C17 C18 -1.2(3) . . . . ?
C16 C17 C18 C13 -1.6(3) . . . . ?
C18 C13 C14 C15 -3.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
