# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2295384'
loop_
_audit_author_name
_audit_author_address
yrc 'Jiangxi Science and Technology Normal University'
_audit_update_record             
;
2023-09-16 deposited with the CCDC.	2023-11-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H16 Br N'
_chemical_formula_weight         398.29

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.3380(14)
_cell_length_b                   12.4628(15)
_cell_length_c                   13.4549(17)
_cell_angle_alpha                90
_cell_angle_beta                 106.655(2)
_cell_angle_gamma                90
_cell_volume                     1821.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2768
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      25.91

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    2.263
_shelx_estimated_absorpt_T_min   0.591
_shelx_estimated_absorpt_T_max   0.613
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9087
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.643
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3192
_reflns_number_gt                2334
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0537P)²+0.3415P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3192
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0932
_refine_ls_wR_factor_gt          0.0860
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_restrained_S_all      0.990
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.55719(3) 0.26480(3) -0.19237(2) 0.07139(16) Uani 1 1 d . . . . .
N1 N 0.38178(18) 0.37746(18) 0.01055(16) 0.0480(6) Uani 1 1 d . . . . .
C11 C 0.5977(2) 0.36355(18) 0.11225(17) 0.0338(5) Uani 1 1 d . . . . .
C10 C 0.6853(2) 0.37200(19) 0.21127(17) 0.0361(5) Uani 1 1 d . . . . .
H10 H 0.7678 0.3573 0.2186 0.043 Uiso 1 1 calc R U . . .
C12 C 0.4724(2) 0.38633(19) 0.10281(18) 0.0379(6) Uani 1 1 d . . . . .
C7 C 0.8002(2) 0.4009(2) 0.48499(18) 0.0406(6) Uani 1 1 d . . . . .
C6 C 0.8821(2) 0.39421(19) 0.58893(18) 0.0391(6) Uani 1 1 d . . . . .
C9 C 0.6489(2) 0.40183(19) 0.29638(18) 0.0375(6) Uani 1 1 d . . . . .
C16 C 0.6301(2) 0.32650(19) 0.02287(17) 0.0370(6) Uani 1 1 d . . . . .
C8 C 0.7340(2) 0.40370(19) 0.39846(18) 0.0392(6) Uani 1 1 d . . . . .
C5 C 1.0075(2) 0.4066(2) 0.6077(2) 0.0489(7) Uani 1 1 d . . . . .
H5 H 1.0398 0.4221 0.5532 0.059 Uiso 1 1 calc R U . . .
C17 C 0.5349(2) 0.3155(2) -0.06639(17) 0.0445(6) Uani 1 1 d . . . . .
C13 C 0.4363(2) 0.4179(2) 0.19143(19) 0.0416(6) Uani 1 1 d . . . . .
C20 C 0.8477(2) 0.3830(2) 0.04963(18) 0.0459(6) Uani 1 1 d . . . . .
H20 H 0.8246 0.4526 0.0607 0.055 Uiso 1 1 calc R U . . .
C18 C 0.4143(2) 0.3428(2) -0.0689(2) 0.0514(7) Uani 1 1 d . . . . .
H18 H 0.3533 0.3357 -0.1317 0.062 Uiso 1 1 calc R U . . .
C19 C 0.7607(2) 0.3020(2) 0.02909(17) 0.0404(6) Uani 1 1 d . . . . .
C14 C 0.5242(2) 0.4256(2) 0.28464(19) 0.0428(6) Uani 1 1 d . . . . .
H14 H 0.5010 0.4474 0.3424 0.051 Uiso 1 1 calc R U . . .
C1 C 0.8364(3) 0.3702(2) 0.6719(2) 0.0514(7) Uani 1 1 d . . . . .
H1 H 0.7521 0.3616 0.6608 0.062 Uiso 1 1 calc R U . . .
C4 C 1.0853(3) 0.3962(2) 0.7070(2) 0.0560(8) Uani 1 1 d . . . . .
H4 H 1.1695 0.4060 0.7189 0.067 Uiso 1 1 calc R U . . .
C3 C 1.0396(3) 0.3716(2) 0.7882(2) 0.0572(8) Uani 1 1 d . . . . .
H3 H 1.0927 0.3635 0.8547 0.069 Uiso 1 1 calc R U . . .
C2 C 0.9154(3) 0.3591(3) 0.7706(2) 0.0609(8) Uani 1 1 d . . . . .
H2 H 0.8840 0.3429 0.8256 0.073 Uiso 1 1 calc R U . . .
C21 C 0.9687(2) 0.3615(3) 0.0539(2) 0.0591(8) Uani 1 1 d . . . . .
H21 H 1.0266 0.4164 0.0679 0.071 Uiso 1 1 calc R U . . .
C24 C 0.7968(3) 0.1983(3) 0.0148(2) 0.0563(7) Uani 1 1 d . . . . .
H24 H 0.7397 0.1427 0.0024 0.068 Uiso 1 1 calc R U . . .
C22 C 1.0032(3) 0.2598(3) 0.0376(2) 0.0694(10) Uani 1 1 d . . . . .
H22 H 1.0843 0.2459 0.0391 0.083 Uiso 1 1 calc R U . . .
C15 C 0.3018(2) 0.4373(3) 0.1814(2) 0.0637(8) Uani 1 1 d . . . . .
H15A H 0.2747 0.5009 0.1410 0.096 Uiso 1 1 calc R U . . .
H15B H 0.2910 0.4463 0.2491 0.096 Uiso 1 1 calc R U . . .
H15C H 0.2541 0.3770 0.1476 0.096 Uiso 1 1 calc R U . . .
C23 C 0.9188(3) 0.1777(3) 0.0190(2) 0.0687(10) Uani 1 1 d . . . . .
H23 H 0.9432 0.1082 0.0092 0.082 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 C17 1.893(2) . ?
N1 C18 1.300(3) . ?
N1 C12 1.370(3) . ?
C11 C10 1.419(3) . ?
C11 C12 1.418(3) . ?
C11 C16 1.431(3) . ?
C10 C9 1.375(3) . ?
C10 H10 0.9300 . ?
C12 C13 1.422(3) . ?
C7 C8 1.191(3) . ?
C7 C6 1.443(3) . ?
C6 C5 1.379(3) . ?
C6 C1 1.392(3) . ?
C9 C14 1.408(3) . ?
C9 C8 1.435(3) . ?
C16 C17 1.372(3) . ?
C16 C19 1.490(3) . ?
C5 C4 1.379(4) . ?
C5 H5 0.9300 . ?
C17 C18 1.400(4) . ?
C13 C14 1.363(3) . ?
C13 C15 1.512(3) . ?
C20 C19 1.383(4) . ?
C20 C21 1.383(4) . ?
C20 H20 0.9300 . ?
C18 H18 0.9300 . ?
C19 C24 1.386(4) . ?
C14 H14 0.9300 . ?
C1 C2 1.379(4) . ?
C1 H1 0.9300 . ?
C4 C3 1.371(4) . ?
C4 H4 0.9300 . ?
C3 C2 1.369(4) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C21 C22 1.362(4) . ?
C21 H21 0.9300 . ?
C24 C23 1.392(4) . ?
C24 H24 0.9300 . ?
C22 C23 1.374(5) . ?
C22 H22 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C23 H23 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
C18 N1 C12 117.1(2) . . ?
C10 C11 C12 118.9(2) . . ?
C10 C11 C16 122.2(2) . . ?
C12 C11 C16 118.8(2) . . ?
C9 C10 C11 120.3(2) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
N1 C12 C13 117.5(2) . . ?
N1 C12 C11 122.5(2) . . ?
C13 C12 C11 120.1(2) . . ?
C8 C7 C6 178.0(3) . . ?
C5 C6 C1 118.6(2) . . ?
C5 C6 C7 121.0(2) . . ?
C1 C6 C7 120.3(2) . . ?
C10 C9 C14 119.7(2) . . ?
C10 C9 C8 121.4(2) . . ?
C14 C9 C8 118.8(2) . . ?
C17 C16 C11 116.1(2) . . ?
C17 C16 C19 123.2(2) . . ?
C11 C16 C19 120.6(2) . . ?
C7 C8 C9 176.1(3) . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C16 C17 C18 121.0(2) . . ?
C16 C17 Br1 122.9(2) . . ?
C18 C17 Br1 116.09(18) . . ?
C14 C13 C12 118.8(2) . . ?
C14 C13 C15 121.6(2) . . ?
C12 C13 C15 119.6(2) . . ?
C19 C20 C21 120.6(3) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
N1 C18 C17 124.5(2) . . ?
N1 C18 H18 117.8 . . ?
C17 C18 H18 117.8 . . ?
C20 C19 C24 119.1(2) . . ?
C20 C19 C16 120.1(2) . . ?
C24 C19 C16 120.7(2) . . ?
C13 C14 C9 122.2(2) . . ?
C13 C14 H14 118.9 . . ?
C9 C14 H14 118.9 . . ?
C2 C1 C6 120.3(3) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C2 C3 C4 119.5(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C22 C21 C20 120.1(3) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C19 C24 C23 119.7(3) . . ?
C19 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C21 C22 C23 120.4(3) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C22 C23 C24 120.1(3) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?

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
C12 C11 C10 C9 0.0(3) . . . . ?
C16 C11 C10 C9 -176.1(2) . . . . ?
C18 N1 C12 C13 -176.3(2) . . . . ?
C18 N1 C12 C11 2.6(4) . . . . ?
C10 C11 C12 N1 -178.3(2) . . . . ?
C16 C11 C12 N1 -2.1(3) . . . . ?
C10 C11 C12 C13 0.5(3) . . . . ?
C16 C11 C12 C13 176.7(2) . . . . ?
C11 C10 C9 C14 -1.0(3) . . . . ?
C11 C10 C9 C8 175.6(2) . . . . ?
C10 C11 C16 C17 175.8(2) . . . . ?
C12 C11 C16 C17 -0.2(3) . . . . ?
C10 C11 C16 C19 -4.2(3) . . . . ?
C12 C11 C16 C19 179.8(2) . . . . ?
C1 C6 C5 C4 -0.5(4) . . . . ?
C7 C6 C5 C4 -177.7(2) . . . . ?
C11 C16 C17 C18 2.0(4) . . . . ?
C19 C16 C17 C18 -178.0(2) . . . . ?
C11 C16 C17 Br1 -178.61(18) . . . . ?
C19 C16 C17 Br1 1.4(4) . . . . ?
N1 C12 C13 C14 178.9(2) . . . . ?
C11 C12 C13 C14 0.0(4) . . . . ?
N1 C12 C13 C15 1.5(4) . . . . ?
C11 C12 C13 C15 -177.4(2) . . . . ?
C12 N1 C18 C17 -0.8(4) . . . . ?
C16 C17 C18 N1 -1.6(4) . . . . ?
Br1 C17 C18 N1 179.0(2) . . . . ?
C21 C20 C19 C24 1.2(3) . . . . ?
C21 C20 C19 C16 -178.9(2) . . . . ?
C17 C16 C19 C20 115.3(3) . . . . ?
C11 C16 C19 C20 -64.6(3) . . . . ?
C17 C16 C19 C24 -64.8(3) . . . . ?
C11 C16 C19 C24 115.2(3) . . . . ?
C12 C13 C14 C9 -1.1(4) . . . . ?
C15 C13 C14 C9 176.3(2) . . . . ?
C10 C9 C14 C13 1.6(4) . . . . ?
C8 C9 C14 C13 -175.1(2) . . . . ?
C5 C6 C1 C2 -0.1(4) . . . . ?
C7 C6 C1 C2 177.1(3) . . . . ?
C6 C5 C4 C3 1.1(4) . . . . ?
C5 C4 C3 C2 -1.1(4) . . . . ?
C4 C3 C2 C1 0.5(5) . . . . ?
C6 C1 C2 C3 0.1(5) . . . . ?
C19 C20 C21 C22 0.1(4) . . . . ?
C20 C19 C24 C23 -1.4(4) . . . . ?
C16 C19 C24 C23 178.8(2) . . . . ?
C20 C21 C22 C23 -1.3(4) . . . . ?
C21 C22 C23 C24 1.2(4) . . . . ?
C19 C24 C23 C22 0.2(4) . . . . ?

_refine_diff_density_max         0.290
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.049

