# 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_yq375
_database_code_depnum_ccdc_archive 'CCDC 2053182'
loop_
_audit_author_name
_audit_author_address
cuixiuling
;Huaqiao University
China
;
_audit_update_record             
;
2020-12-30 deposited with the CCDC.	2026-05-04 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            'C17 H13 Br N2 O'
_chemical_formula_weight         341.20

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'
O O 0.0492 0.0322 '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/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.2783(3)
_cell_length_b                   13.5508(4)
_cell_length_c                   14.8298(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.097(3)
_cell_angle_gamma                90
_cell_volume                     1435.28(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    3.898
_shelx_estimated_absorpt_T_min   0.611
_shelx_estimated_absorpt_T_max   0.746
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5282
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.458
_diffrn_reflns_theta_max         67.076
_diffrn_reflns_theta_full        67.076
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2568
_reflns_number_gt                2079
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0569P)²+0.9250P] 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         2568
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1214
_refine_ls_wR_factor_gt          0.1115
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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 0.47741(7) 0.44152(3) 0.37569(3) 0.0674(2) Uani 1 1 d . . . . .
C1 C 0.4037(5) 0.6608(3) 0.2833(2) 0.0420(7) Uani 1 1 d . . . . .
C2 C 0.5945(5) 0.6126(2) 0.2848(2) 0.0389(7) Uani 1 1 d . . . . .
C3 C 0.7459(4) 0.6363(2) 0.3688(2) 0.0372(7) Uani 1 1 d . . . . .
C4 C 0.7230(4) 0.7127(2) 0.4283(2) 0.0365(7) Uani 1 1 d . . . . .
C5 C 0.8683(5) 0.7387(3) 0.5008(2) 0.0450(8) Uani 1 1 d . . . . .
H5 H 0.8518 0.7898 0.5403 0.054 Uiso 1 1 calc R U . . .
C6 C 1.0352(5) 0.6886(3) 0.5134(3) 0.0524(9) Uani 1 1 d . . . . .
H6 H 1.1319 0.7057 0.5616 0.063 Uiso 1 1 calc R U . . .
C7 C 1.0594(5) 0.6129(3) 0.4549(3) 0.0525(9) Uani 1 1 d . . . . .
H7 H 1.1722 0.5787 0.4639 0.063 Uiso 1 1 calc R U . . .
C8 C 0.9167(5) 0.5876(3) 0.3829(3) 0.0464(8) Uani 1 1 d . . . . .
H8 H 0.9355 0.5370 0.3432 0.056 Uiso 1 1 calc R U . . .
C9 C 0.5629(5) 0.5017(3) 0.2718(3) 0.0491(9) Uani 1 1 d . . . . .
H9A H 0.6789 0.4706 0.2641 0.059 Uiso 1 1 calc R U . . .
H9B H 0.4705 0.4902 0.2163 0.059 Uiso 1 1 calc R U . . .
C10 C 0.6586(6) 0.6526(3) 0.1981(2) 0.0547(9) Uani 1 1 d . . . . .
H10A H 0.5671 0.6361 0.1445 0.082 Uiso 1 1 calc R U . . .
H10B H 0.7767 0.6237 0.1935 0.082 Uiso 1 1 calc R U . . .
H10C H 0.6716 0.7231 0.2026 0.082 Uiso 1 1 calc R U . . .
C11 C 0.5488(4) 0.7677(2) 0.4136(2) 0.0352(7) Uani 1 1 d . . . . .
C12 C 0.2558(4) 0.8065(2) 0.3452(2) 0.0356(7) Uani 1 1 d . . . . .
C13 C 0.3256(4) 0.8704(2) 0.4174(2) 0.0375(7) Uani 1 1 d . . . . .
C14 C 0.2177(5) 0.9488(3) 0.4377(3) 0.0481(8) Uani 1 1 d . . . . .
H14 H 0.2621 0.9916 0.4861 0.058 Uiso 1 1 calc R U . . .
C15 C 0.0425(6) 0.9610(3) 0.3839(3) 0.0545(9) Uani 1 1 d . . . . .
H15 H -0.0323 1.0132 0.3958 0.065 Uiso 1 1 calc R U . . .
C16 C -0.0245(5) 0.8964(3) 0.3120(3) 0.0531(9) Uani 1 1 d . . . . .
H16 H -0.1434 0.9066 0.2769 0.064 Uiso 1 1 calc R U . . .
C17 C 0.0802(5) 0.8178(3) 0.2912(2) 0.0453(8) Uani 1 1 d . . . . .
H17 H 0.0350 0.7747 0.2432 0.054 Uiso 1 1 calc R U . . .
N1 N 0.4014(3) 0.73937(19) 0.34266(18) 0.0346(6) Uani 1 1 d . . . . .
N2 N 0.5081(4) 0.8446(2) 0.45842(18) 0.0408(6) Uani 1 1 d . . . . .
O1 O 0.2654(4) 0.6375(2) 0.2294(2) 0.0632(8) 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
Br1 C9 1.949(4) . ?
C1 O1 1.201(4) . ?
C1 N1 1.383(4) . ?
C1 C2 1.532(5) . ?
C2 C9 1.526(5) . ?
C2 C3 1.530(4) . ?
C2 C10 1.548(5) . ?
C3 C8 1.388(5) . ?
C3 C4 1.391(5) . ?
C4 C5 1.400(4) . ?
C4 C11 1.451(4) . ?
C5 C6 1.373(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.376(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.382(5) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 N2 1.300(4) . ?
C11 N1 1.404(4) . ?
C12 C17 1.380(5) . ?
C12 C13 1.394(4) . ?
C12 N1 1.403(4) . ?
C13 C14 1.388(5) . ?
C13 N2 1.395(4) . ?
C14 C15 1.378(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.394(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.379(5) . ?
C16 H16 0.9300 . ?
C17 H17 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
O1 C1 N1 121.0(3) . . ?
O1 C1 C2 122.6(3) . . ?
N1 C1 C2 116.2(3) . . ?
C9 C2 C3 112.2(3) . . ?
C9 C2 C1 107.7(3) . . ?
C3 C2 C1 115.5(3) . . ?
C9 C2 C10 107.6(3) . . ?
C3 C2 C10 108.5(3) . . ?
C1 C2 C10 104.8(3) . . ?
C8 C3 C4 118.1(3) . . ?
C8 C3 C2 120.4(3) . . ?
C4 C3 C2 121.2(3) . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 C11 119.6(3) . . ?
C5 C4 C11 119.7(3) . . ?
C6 C5 C4 119.9(3) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 120.0(3) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C8 120.3(3) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C7 C8 C3 121.1(4) . . ?
C7 C8 H8 119.5 . . ?
C3 C8 H8 119.5 . . ?
C2 C9 Br1 112.0(2) . . ?
C2 C9 H9A 109.2 . . ?
Br1 C9 H9A 109.2 . . ?
C2 C9 H9B 109.2 . . ?
Br1 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C2 C10 H10A 109.5 . . ?
C2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 N1 112.7(3) . . ?
N2 C11 C4 127.8(3) . . ?
N1 C11 C4 119.5(3) . . ?
C17 C12 C13 122.5(3) . . ?
C17 C12 N1 132.5(3) . . ?
C13 C12 N1 105.0(3) . . ?
C14 C13 C12 120.3(3) . . ?
C14 C13 N2 128.9(3) . . ?
C12 C13 N2 110.8(3) . . ?
C15 C14 C13 117.7(3) . . ?
C15 C14 H14 121.1 . . ?
C13 C14 H14 121.1 . . ?
C14 C15 C16 121.1(3) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C17 C16 C15 122.0(4) . . ?
C17 C16 H16 119.0 . . ?
C15 C16 H16 119.0 . . ?
C16 C17 C12 116.5(3) . . ?
C16 C17 H17 121.8 . . ?
C12 C17 H17 121.8 . . ?
C1 N1 C12 128.2(3) . . ?
C1 N1 C11 125.9(3) . . ?
C12 N1 C11 105.9(3) . . ?
C11 N2 C13 105.6(3) . . ?

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 C9 -42.3(5) . . . . ?
N1 C1 C2 C9 143.1(3) . . . . ?
O1 C1 C2 C3 -168.6(3) . . . . ?
N1 C1 C2 C3 16.8(4) . . . . ?
O1 C1 C2 C10 72.1(4) . . . . ?
N1 C1 C2 C10 -102.5(3) . . . . ?
C9 C2 C3 C8 48.2(4) . . . . ?
C1 C2 C3 C8 172.2(3) . . . . ?
C10 C2 C3 C8 -70.5(4) . . . . ?
C9 C2 C3 C4 -137.4(3) . . . . ?
C1 C2 C3 C4 -13.5(5) . . . . ?
C10 C2 C3 C4 103.8(4) . . . . ?
C8 C3 C4 C5 -0.5(5) . . . . ?
C2 C3 C4 C5 -175.0(3) . . . . ?
C8 C3 C4 C11 177.7(3) . . . . ?
C2 C3 C4 C11 3.3(5) . . . . ?
C3 C4 C5 C6 0.0(5) . . . . ?
C11 C4 C5 C6 -178.2(3) . . . . ?
C4 C5 C6 C7 0.0(6) . . . . ?
C5 C6 C7 C8 0.5(6) . . . . ?
C6 C7 C8 C3 -1.0(6) . . . . ?
C4 C3 C8 C7 1.0(5) . . . . ?
C2 C3 C8 C7 175.5(3) . . . . ?
C3 C2 C9 Br1 61.6(3) . . . . ?
C1 C2 C9 Br1 -66.6(3) . . . . ?
C10 C2 C9 Br1 -179.1(2) . . . . ?
C3 C4 C11 N2 -175.2(3) . . . . ?
C5 C4 C11 N2 3.0(5) . . . . ?
C3 C4 C11 N1 3.8(5) . . . . ?
C5 C4 C11 N1 -178.0(3) . . . . ?
C17 C12 C13 C14 0.4(5) . . . . ?
N1 C12 C13 C14 178.3(3) . . . . ?
C17 C12 C13 N2 -177.8(3) . . . . ?
N1 C12 C13 N2 0.1(3) . . . . ?
C12 C13 C14 C15 -0.6(5) . . . . ?
N2 C13 C14 C15 177.2(3) . . . . ?
C13 C14 C15 C16 0.5(6) . . . . ?
C14 C15 C16 C17 0.0(6) . . . . ?
C15 C16 C17 C12 -0.2(6) . . . . ?
C13 C12 C17 C16 0.1(5) . . . . ?
N1 C12 C17 C16 -177.2(3) . . . . ?
O1 C1 N1 C12 -6.1(6) . . . . ?
C2 C1 N1 C12 168.6(3) . . . . ?
O1 C1 N1 C11 174.0(3) . . . . ?
C2 C1 N1 C11 -11.3(5) . . . . ?
C17 C12 N1 C1 -2.3(6) . . . . ?
C13 C12 N1 C1 -179.9(3) . . . . ?
C17 C12 N1 C11 177.6(3) . . . . ?
C13 C12 N1 C11 0.0(3) . . . . ?
N2 C11 N1 C1 179.8(3) . . . . ?
C4 C11 N1 C1 0.6(5) . . . . ?
N2 C11 N1 C12 -0.1(4) . . . . ?
C4 C11 N1 C12 -179.3(3) . . . . ?
N1 C11 N2 C13 0.2(4) . . . . ?
C4 C11 N2 C13 179.3(3) . . . . ?
C14 C13 N2 C11 -178.2(3) . . . . ?
C12 C13 N2 C11 -0.2(4) . . . . ?

_refine_diff_density_max         0.448
_refine_diff_density_min         -0.711
_refine_diff_density_rms         0.066

