# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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. 
# 
#######################################################################

data_2-20240803
_database_code_depnum_ccdc_archive 'CCDC 2375417'
loop_
_audit_author_name
_audit_author_address
'Kelu Yan'
;Qufu Normal University
China
;
_audit_update_record             
;
2024-08-03 deposited with the CCDC.	2025-04-09 downloaded from the CCDC.
;
_audit_creation_date             2024-08-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H14 Br N O3'
_chemical_formula_sum            'C18 H14 Br N O3'
_chemical_formula_weight         372.21
_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                   7.3081(8)
_cell_length_b                   8.5016(9)
_cell_length_c                   14.2301(15)
_cell_angle_alpha                99.451(4)
_cell_angle_beta                 100.327(3)
_cell_angle_gamma                107.469(3)
_cell_volume                     806.98(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3466
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.863
_cell_measurement_theta_min      2.667
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.561
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6126
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0967 before and 0.0515 after correction.
The Ratio of minimum to maximum transmission is 0.8215.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_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  0.0708
_diffrn_reflns_av_unetI/netI     0.0846
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17850
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.304
_diffrn_reflns_theta_min         2.582
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_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                1776
_reflns_number_total             4008
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         4008
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1536
_refine_ls_R_factor_gt           0.0465
_refine_ls_restrained_S_all      0.991
_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)+(0.0246P)²+0.2399P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0693
_refine_ls_wR_factor_ref         0.0919
_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:
 C11(H11A,H11B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C4(H4), C1(H1), C18(H18), C14(H14), C15(H15), C9(H9), C3(H3),
 C17(H17), C2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.94487(6) 0.68929(6) 1.17124(3) 0.0903(2) Uani 1 1 d . . . . .
O2 O 0.3723(3) 0.8645(3) 0.79896(15) 0.0543(5) Uani 1 1 d . . . . .
O1 O 0.0944(3) 0.7610(3) 0.50171(16) 0.0673(7) Uani 1 1 d . . . . .
N1 N 0.4062(4) 0.8893(3) 0.59657(17) 0.0468(6) Uani 1 1 d . . . . .
O3 O 0.1453(3) 0.7868(3) 0.88376(16) 0.0727(7) Uani 1 1 d . . . . .
C6 C 0.3516(4) 0.6817(4) 0.4481(2) 0.0411(7) Uani 1 1 d . . . . .
C5 C 0.5534(4) 0.7032(4) 0.4674(2) 0.0427(7) Uani 1 1 d . . . . .
C13 C 0.4683(4) 0.7829(4) 0.9448(2) 0.0472(8) Uani 1 1 d . . . . .
C12 C 0.3101(5) 0.8096(4) 0.8747(2) 0.0496(8) Uani 1 1 d . . . . .
C7 C 0.2706(5) 0.7755(4) 0.5144(2) 0.0499(8) Uani 1 1 d . . . . .
C8 C 0.6809(4) 0.8240(4) 0.5545(2) 0.0508(8) Uani 1 1 d . . . . .
H8 H 0.8157 0.8413 0.5692 0.061 Uiso 1 1 calc R . . . .
C4 C 0.6216(4) 0.6082(4) 0.4004(2) 0.0529(8) Uani 1 1 d . . . . .
H4 H 0.7551 0.6202 0.4128 0.064 Uiso 1 1 calc R . . . .
C1 C 0.2227(4) 0.5671(4) 0.3628(2) 0.0525(8) Uani 1 1 d . . . . .
H1 H 0.0884 0.5518 0.3499 0.063 Uiso 1 1 calc R . . . .
C18 C 0.4216(5) 0.7216(4) 1.0249(2) 0.0559(9) Uani 1 1 d . . . . .
H18 H 0.2938 0.6990 1.0335 0.067 Uiso 1 1 calc R . . . .
C14 C 0.6597(5) 0.8152(4) 0.9329(2) 0.0568(9) Uani 1 1 d . . . . .
H14 H 0.6929 0.8567 0.8794 0.068 Uiso 1 1 calc R . . . .
C15 C 0.8016(5) 0.7862(4) 0.9999(2) 0.0619(9) Uani 1 1 d . . . . .
H15 H 0.9292 0.8067 0.9914 0.074 Uiso 1 1 calc R . . . .
C9 C 0.6067(4) 0.9114(4) 0.6143(2) 0.0531(8) Uani 1 1 d . . . . .
H9 H 0.6921 0.9903 0.6700 0.064 Uiso 1 1 calc R . . . .
C3 C 0.4944(5) 0.4987(4) 0.3175(2) 0.0586(9) Uani 1 1 d . . . . .
H3 H 0.5415 0.4372 0.2734 0.070 Uiso 1 1 calc R . . . .
C17 C 0.5628(5) 0.6936(4) 1.0923(2) 0.0596(9) Uani 1 1 d . . . . .
H17 H 0.5308 0.6526 1.1461 0.072 Uiso 1 1 calc R . . . .
C16 C 0.7509(5) 0.7269(4) 1.0788(2) 0.0576(9) Uani 1 1 d . . . . .
C11 C 0.2262(4) 0.8955(4) 0.7287(2) 0.0553(8) Uani 1 1 d . . . . .
H11A H 0.1599 0.9618 0.7624 0.066 Uiso 1 1 calc R . . . .
H11B H 0.1278 0.7889 0.6904 0.066 Uiso 1 1 calc R . . . .
C10 C 0.3309(5) 0.9907(4) 0.6623(2) 0.0562(9) Uani 1 1 d . . . . .
H10A H 0.2400 1.0316 0.6233 0.067 Uiso 1 1 calc R . . . .
H10B H 0.4404 1.0887 0.7025 0.067 Uiso 1 1 calc R . . . .
C2 C 0.2939(5) 0.4780(4) 0.2984(2) 0.0622(9) Uani 1 1 d . . . . .
H2 H 0.2080 0.4030 0.2415 0.075 Uiso 1 1 calc R . . . .


_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 C16 1.893(3) . ?
O2 C12 1.341(3) . ?
O2 C11 1.443(3) . ?
O1 C7 1.233(3) . ?
N1 C7 1.386(4) . ?
N1 C9 1.390(4) . ?
N1 C10 1.459(3) . ?
O3 C12 1.195(3) . ?
C6 C5 1.400(4) . ?
C6 C7 1.454(4) . ?
C6 C1 1.400(4) . ?
C5 C8 1.433(4) . ?
C5 C4 1.404(4) . ?
C13 C12 1.484(4) . ?
C13 C18 1.383(4) . ?
C13 C14 1.390(4) . ?
C8 C9 1.331(4) . ?
C4 C3 1.359(4) . ?
C1 C2 1.365(4) . ?
C18 C17 1.381(4) . ?
C14 C15 1.386(4) . ?
C15 C16 1.369(4) . ?
C3 C2 1.392(4) . ?
C17 C16 1.373(4) . ?
C11 C10 1.506(4) . ?

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
C12 O2 C11 115.3(2) . . ?
C7 N1 C9 121.9(3) . . ?
C7 N1 C10 117.1(3) . . ?
C9 N1 C10 120.9(3) . . ?
C5 C6 C7 121.8(3) . . ?
C5 C6 C1 119.7(3) . . ?
C1 C6 C7 118.5(3) . . ?
C6 C5 C8 117.9(3) . . ?
C6 C5 C4 118.9(3) . . ?
C4 C5 C8 123.2(3) . . ?
C18 C13 C12 118.3(3) . . ?
C18 C13 C14 118.9(3) . . ?
C14 C13 C12 122.8(3) . . ?
O2 C12 C13 112.5(3) . . ?
O3 C12 O2 122.9(3) . . ?
O3 C12 C13 124.6(3) . . ?
O1 C7 N1 119.5(3) . . ?
O1 C7 C6 124.7(3) . . ?
N1 C7 C6 115.8(3) . . ?
C9 C8 C5 120.1(3) . . ?
C3 C4 C5 120.6(3) . . ?
C2 C1 C6 120.1(3) . . ?
C17 C18 C13 120.7(3) . . ?
C15 C14 C13 120.6(3) . . ?
C16 C15 C14 119.0(3) . . ?
C8 C9 N1 122.4(3) . . ?
C4 C3 C2 120.4(3) . . ?
C16 C17 C18 119.2(3) . . ?
C15 C16 Br1 119.1(3) . . ?
C15 C16 C17 121.6(3) . . ?
C17 C16 Br1 119.2(3) . . ?
O2 C11 C10 107.9(2) . . ?
N1 C10 C11 113.7(2) . . ?
C1 C2 C3 120.4(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
