# Supplementary Information (SI) for ChemComm.
# 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_XY234_0m
_database_code_depnum_ccdc_archive 'CCDC 2412290'
loop_
_audit_author_name
_audit_author_address
'Yan-Ping Zhu'
;Yantai University
China
;
_audit_update_record             
;
2024-12-22 deposited with the CCDC.	2025-02-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H8 Br F2 N O'
_chemical_formula_weight         288.09

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   23.396(10)
_cell_length_b                   6.177(3)
_cell_length_c                   16.234(7)
_cell_angle_alpha                90
_cell_angle_beta                 111.845(6)
_cell_angle_gamma                90
_cell_volume                     2177.6(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1970
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      26.14

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.757
_exptl_crystal_F_000             1136
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    3.779
_shelx_estimated_absorpt_T_min   0.534
_shelx_estimated_absorpt_T_max   0.583
_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      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6425
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.876
_diffrn_reflns_theta_max         27.556
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2490
_reflns_number_gt                1787
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0600P)²] 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         2490
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1137
_refine_ls_wR_factor_gt          0.1047
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.000
_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 0.10500(2) 0.82092(7) 0.67833(2) 0.05609(18) Uani 1 1 d . . . . .
F1 F 0.45763(9) 0.3717(3) 0.65954(13) 0.0590(6) Uani 1 1 d . . . . .
F2 F 0.43175(10) 0.4177(4) 0.51905(13) 0.0639(6) Uani 1 1 d . . . . .
O2 O 0.32670(11) 0.3090(3) 0.55660(19) 0.0566(7) Uani 1 1 d . . . . .
N1 N 0.33825(11) 0.6629(4) 0.60688(15) 0.0289(5) Uani 1 1 d . . . . .
C1 C 0.17545(13) 0.7747(5) 0.64976(19) 0.0363(7) Uani 1 1 d . . . . .
C2 C 0.22009(14) 0.9337(5) 0.6701(2) 0.0410(7) Uani 1 1 d . . . . .
H6 H 0.214488 1.064707 0.694234 0.049 Uiso 1 1 calc R U . . .
C3 C 0.27328(14) 0.8953(5) 0.6539(2) 0.0384(7) Uani 1 1 d . . . . .
H1 H 0.303467 1.001855 0.667297 0.046 Uiso 1 1 calc R U . . .
C4 C 0.28217(12) 0.7007(4) 0.61819(18) 0.0290(6) Uani 1 1 d . . . . .
C5 C 0.38698(15) 0.8281(5) 0.6327(3) 0.0445(8) Uani 1 1 d . . . . .
H5 H 0.401842 0.855424 0.696087 0.053 Uiso 1 1 calc R U . . .
H4 H 0.372145 0.962814 0.601343 0.053 Uiso 1 1 calc R U . . .
C6 C 0.43684(15) 0.7310(6) 0.6067(3) 0.0456(8) Uani 1 1 d . . . . .
C7 C 0.23570(13) 0.5469(5) 0.59519(19) 0.0385(7) Uani 1 1 d . . . . .
H3 H 0.240342 0.417350 0.569194 0.046 Uiso 1 1 calc R U . . .
C8 C 0.18276(13) 0.5858(6) 0.6108(2) 0.0431(8) Uani 1 1 d . . . . .
H2 H 0.151574 0.482641 0.594628 0.052 Uiso 1 1 calc R U . . .
C9 C 0.42260(13) 0.4982(5) 0.59044(19) 0.0388(7) Uani 1 1 d . . . . .
C10 C 0.35596(13) 0.4756(5) 0.58116(18) 0.0333(7) Uani 1 1 d . . . . .
C11 C 0.4824(2) 0.8318(7) 0.5950(4) 0.0862(16) Uani 1 1 d . . . . .
H11A H 0.509038 0.756075 0.574887 0.103 Uiso 1 1 calc R U . . .
H11B H 0.488212 0.979212 0.606857 0.103 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 C1 1.893(3) . ?
F1 C9 1.362(3) . ?
F2 C9 1.349(3) . ?
O2 C10 1.218(4) . ?
N1 C10 1.347(4) . ?
N1 C4 1.410(3) . ?
N1 C5 1.470(4) . ?
C1 C8 1.368(5) . ?
C1 C2 1.381(4) . ?
C2 C3 1.384(4) . ?
C2 H6 0.9300 . ?
C3 C4 1.384(4) . ?
C3 H1 0.9300 . ?
C4 C7 1.386(4) . ?
C5 C6 1.505(4) . ?
C5 H5 0.9700 . ?
C5 H4 0.9700 . ?
C6 C11 1.308(5) . ?
C6 C9 1.478(5) . ?
C7 C8 1.374(4) . ?
C7 H3 0.9300 . ?
C8 H2 0.9300 . ?
C9 C10 1.516(4) . ?
C11 H11A 0.9300 . ?
C11 H11B 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
C10 N1 C4 126.2(2) . . ?
C10 N1 C5 112.9(2) . . ?
C4 N1 C5 120.6(2) . . ?
C8 C1 C2 120.2(3) . . ?
C8 C1 Br1 120.8(2) . . ?
C2 C1 Br1 119.0(2) . . ?
C1 C2 C3 119.1(3) . . ?
C1 C2 H6 120.4 . . ?
C3 C2 H6 120.4 . . ?
C2 C3 C4 120.9(3) . . ?
C2 C3 H1 119.5 . . ?
C4 C3 H1 119.5 . . ?
C3 C4 C7 118.9(3) . . ?
C3 C4 N1 119.4(2) . . ?
C7 C4 N1 121.8(2) . . ?
N1 C5 C6 104.1(2) . . ?
N1 C5 H5 110.9 . . ?
C6 C5 H5 110.9 . . ?
N1 C5 H4 110.9 . . ?
C6 C5 H4 110.9 . . ?
H5 C5 H4 109.0 . . ?
C11 C6 C9 125.4(3) . . ?
C11 C6 C5 127.6(4) . . ?
C9 C6 C5 106.9(3) . . ?
C8 C7 C4 120.1(3) . . ?
C8 C7 H3 120.0 . . ?
C4 C7 H3 120.0 . . ?
C1 C8 C7 120.7(3) . . ?
C1 C8 H2 119.7 . . ?
C7 C8 H2 119.7 . . ?
F2 C9 F1 104.9(2) . . ?
F2 C9 C6 114.5(3) . . ?
F1 C9 C6 112.6(3) . . ?
F2 C9 C10 111.5(2) . . ?
F1 C9 C10 108.1(2) . . ?
C6 C9 C10 105.2(2) . . ?
O2 C10 N1 128.8(3) . . ?
O2 C10 C9 122.9(3) . . ?
N1 C10 C9 108.3(3) . . ?
C6 C11 H11A 120.0 . . ?
C6 C11 H11B 120.0 . . ?
H11A C11 H11B 120.0 . . ?

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
C8 C1 C2 C3 -2.7(5) . . . . ?
Br1 C1 C2 C3 176.3(2) . . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C2 C3 C4 C7 2.6(5) . . . . ?
C2 C3 C4 N1 -176.8(3) . . . . ?
C10 N1 C4 C3 173.3(3) . . . . ?
C5 N1 C4 C3 0.0(4) . . . . ?
C10 N1 C4 C7 -6.1(4) . . . . ?
C5 N1 C4 C7 -179.4(3) . . . . ?
C10 N1 C5 C6 8.3(4) . . . . ?
C4 N1 C5 C6 -177.6(3) . . . . ?
N1 C5 C6 C11 161.3(5) . . . . ?
N1 C5 C6 C9 -14.9(4) . . . . ?
C3 C4 C7 C8 -2.2(4) . . . . ?
N1 C4 C7 C8 177.2(3) . . . . ?
C2 C1 C8 C7 3.2(5) . . . . ?
Br1 C1 C8 C7 -175.9(2) . . . . ?
C4 C7 C8 C1 -0.7(5) . . . . ?
C11 C6 C9 F2 -37.6(6) . . . . ?
C5 C6 C9 F2 138.7(3) . . . . ?
C11 C6 C9 F1 82.1(5) . . . . ?
C5 C6 C9 F1 -101.6(3) . . . . ?
C11 C6 C9 C10 -160.4(4) . . . . ?
C5 C6 C9 C10 15.9(4) . . . . ?
C4 N1 C10 O2 5.9(5) . . . . ?
C5 N1 C10 O2 179.5(3) . . . . ?
C4 N1 C10 C9 -172.1(2) . . . . ?
C5 N1 C10 C9 1.6(3) . . . . ?
F2 C9 C10 O2 46.1(4) . . . . ?
F1 C9 C10 O2 -68.7(4) . . . . ?
C6 C9 C10 O2 170.8(3) . . . . ?
F2 C9 C10 N1 -135.8(3) . . . . ?
F1 C9 C10 N1 109.4(3) . . . . ?
C6 C9 C10 N1 -11.1(3) . . . . ?

_refine_diff_density_max         0.433
_refine_diff_density_min         -0.901
_refine_diff_density_rms         0.165



