# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2417861'
loop_
_audit_author_name
_audit_author_address
'Feng Li'
;Zaozhuang University
China
;
_audit_update_record             
;
2025-01-18 deposited with the CCDC.	2025-04-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H13 F4 N O2'
_chemical_formula_weight         351.29

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'
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'

_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                   8.8404(2)
_cell_length_b                   11.5522(3)
_cell_length_c                   15.9026(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.5930(10)
_cell_angle_gamma                90
_cell_volume                     1605.84(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9960
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      27.47

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.126
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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      273(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            65013
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.491
_diffrn_reflns_theta_max         27.529
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             3666
_reflns_number_gt                3154
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0949P)²+0.5399P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.230(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3666
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0576
_refine_ls_wR_factor_ref         0.1638
_refine_ls_wR_factor_gt          0.1432
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
F1 F 0.03204(13) 0.55077(13) 0.12115(9) 0.0676(4) Uani 1 1 d . . . . .
F2 F 0.17746(15) 0.46537(15) 0.04401(7) 0.0756(5) Uani 1 1 d . . . . .
F3 F 0.09243(14) 0.37319(12) 0.14375(9) 0.0656(4) Uani 1 1 d . . . . .
C3 C 0.41948(17) 0.43081(14) 0.17757(10) 0.0351(4) Uani 1 1 d . . . . .
F4 F 0.60715(16) 0.15567(11) 0.21342(10) 0.0740(4) Uani 1 1 d . . . . .
O1 O 0.27979(17) 0.72003(12) 0.15233(9) 0.0554(4) Uani 1 1 d . . . . .
O2 O 0.46909(15) 0.62545(11) 0.31606(8) 0.0472(3) Uani 1 1 d . . . . .
C2 C 0.4437(2) 0.31737(14) 0.20235(11) 0.0404(4) Uani 1 1 d . . . . .
H2 H 0.371612 0.276128 0.227208 0.049 Uiso 1 1 calc R U . . .
N1 N 0.47918(18) 0.60539(14) 0.12359(10) 0.0464(4) Uani 1 1 d . . . . .
C1 C 0.5801(2) 0.26742(17) 0.18866(13) 0.0503(5) Uani 1 1 d . . . . .
C4 C 0.5289(2) 0.49161(15) 0.14084(11) 0.0416(4) Uani 1 1 d . . . . .
C5 C 0.6648(2) 0.44003(19) 0.12806(14) 0.0550(5) Uani 1 1 d . . . . .
H5 H 0.737423 0.481000 0.103453 0.066 Uiso 1 1 calc R U . . .
C6 C 0.6900(2) 0.3258(2) 0.15283(15) 0.0586(5) Uani 1 1 d . . . . .
H6 H 0.780495 0.288916 0.145275 0.070 Uiso 1 1 calc R U . . .
C7 C 0.28732(17) 0.51091(13) 0.18516(9) 0.0339(3) Uani 1 1 d . . . . .
C8 C 0.3447(2) 0.62751(15) 0.15331(10) 0.0408(4) Uani 1 1 d . . . . .
C9 C 0.5708(3) 0.6952(2) 0.09250(19) 0.0748(7) Uani 1 1 d . . . . .
H9A H 0.668165 0.699583 0.128324 0.112 Uiso 1 1 calc R U . . .
H9B H 0.519025 0.768131 0.093176 0.112 Uiso 1 1 calc R U . . .
H9C H 0.585934 0.677301 0.035395 0.112 Uiso 1 1 calc R U . . .
C10 C 0.1464(2) 0.47511(18) 0.12315(11) 0.0467(4) Uani 1 1 d . . . . .
C11 C 0.24217(17) 0.51665(13) 0.27455(9) 0.0347(3) Uani 1 1 d . . . . .
H11A H 0.145043 0.556683 0.271453 0.042 Uiso 1 1 calc R U . . .
H11B H 0.228138 0.438532 0.294372 0.042 Uiso 1 1 calc R U . . .
C12 C 0.35951(18) 0.57779(13) 0.33836(10) 0.0347(3) Uani 1 1 d . . . . .
C13 C 0.33410(19) 0.57831(14) 0.42901(10) 0.0385(4) Uani 1 1 d . . . . .
C14 C 0.2260(2) 0.50793(19) 0.45835(12) 0.0516(5) Uani 1 1 d . . . . .
H14 H 0.162108 0.461836 0.420425 0.062 Uiso 1 1 calc R U . . .
C15 C 0.2133(3) 0.5063(2) 0.54438(13) 0.0601(5) Uani 1 1 d . . . . .
H15 H 0.141770 0.458267 0.564131 0.072 Uiso 1 1 calc R U . . .
C16 C 0.3063(3) 0.5756(2) 0.60029(12) 0.0580(6) Uani 1 1 d . . . . .
H16 H 0.297825 0.574056 0.657880 0.070 Uiso 1 1 calc R U . . .
C17 C 0.4113(3) 0.64696(19) 0.57161(12) 0.0568(5) Uani 1 1 d . . . . .
H17 H 0.472560 0.694664 0.609634 0.068 Uiso 1 1 calc R U . . .
C18 C 0.4265(2) 0.64832(16) 0.48632(11) 0.0469(4) Uani 1 1 d . . . . .
H18 H 0.498849 0.696244 0.467283 0.056 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
F1 C10 1.333(2) . ?
F2 C10 1.333(2) . ?
F3 C10 1.329(2) . ?
C3 C2 1.376(2) . ?
C3 C4 1.393(2) . ?
C3 C7 1.509(2) . ?
F4 C1 1.360(2) . ?
O1 C8 1.212(2) . ?
O2 C12 1.212(2) . ?
C2 C1 1.382(2) . ?
C2 H2 0.9300 . ?
N1 C8 1.368(2) . ?
N1 C4 1.400(2) . ?
N1 C9 1.448(2) . ?
C1 C6 1.374(3) . ?
C4 C5 1.383(3) . ?
C5 C6 1.386(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C10 1.526(2) . ?
C7 C11 1.534(2) . ?
C7 C8 1.551(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C11 C12 1.513(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.492(2) . ?
C13 C14 1.387(3) . ?
C13 C18 1.389(2) . ?
C14 C15 1.390(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.375(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.370(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.383(3) . ?
C17 H17 0.9300 . ?
C18 H18 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
C2 C3 C4 120.81(15) . . ?
C2 C3 C7 130.56(14) . . ?
C4 C3 C7 108.60(14) . . ?
C3 C2 C1 117.03(16) . . ?
C3 C2 H2 121.5 . . ?
C1 C2 H2 121.5 . . ?
C8 N1 C4 111.81(13) . . ?
C8 N1 C9 122.94(18) . . ?
C4 N1 C9 124.34(17) . . ?
F4 C1 C6 118.73(17) . . ?
F4 C1 C2 118.06(17) . . ?
C6 C1 C2 123.20(18) . . ?
C5 C4 C3 121.16(17) . . ?
C5 C4 N1 129.05(16) . . ?
C3 C4 N1 109.77(14) . . ?
C4 C5 C6 118.36(17) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C1 C6 C5 119.43(18) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C3 C7 C10 110.44(13) . . ?
C3 C7 C11 114.35(13) . . ?
C10 C7 C11 108.06(12) . . ?
C3 C7 C8 102.22(12) . . ?
C10 C7 C8 107.43(13) . . ?
C11 C7 C8 114.08(13) . . ?
O1 C8 N1 126.48(16) . . ?
O1 C8 C7 126.38(16) . . ?
N1 C8 C7 107.10(14) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
F3 C10 F2 106.87(16) . . ?
F3 C10 F1 106.74(15) . . ?
F2 C10 F1 107.19(16) . . ?
F3 C10 C7 111.65(15) . . ?
F2 C10 C7 111.68(14) . . ?
F1 C10 C7 112.38(15) . . ?
C12 C11 C7 113.22(12) . . ?
C12 C11 H11A 108.9 . . ?
C7 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C7 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
O2 C12 C13 121.54(15) . . ?
O2 C12 C11 120.89(14) . . ?
C13 C12 C11 117.57(13) . . ?
C14 C13 C18 119.19(16) . . ?
C14 C13 C12 122.23(15) . . ?
C18 C13 C12 118.53(16) . . ?
C13 C14 C15 120.04(19) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 120.0(2) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C15 120.33(18) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 120.24(19) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C13 120.19(19) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 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
C4 C3 C2 C1 -0.3(2) . . . . ?
C7 C3 C2 C1 -178.27(16) . . . . ?
C3 C2 C1 F4 179.37(17) . . . . ?
C3 C2 C1 C6 0.6(3) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C7 C3 C4 C5 178.43(16) . . . . ?
C2 C3 C4 N1 -178.39(15) . . . . ?
C7 C3 C4 N1 -0.05(19) . . . . ?
C8 N1 C4 C5 -173.54(19) . . . . ?
C9 N1 C4 C5 -4.2(3) . . . . ?
C8 N1 C4 C3 4.8(2) . . . . ?
C9 N1 C4 C3 174.2(2) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
N1 C4 C5 C6 178.09(19) . . . . ?
F4 C1 C6 C5 -179.4(2) . . . . ?
C2 C1 C6 C5 -0.6(3) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C2 C3 C7 C10 -71.8(2) . . . . ?
C4 C3 C7 C10 110.13(15) . . . . ?
C2 C3 C7 C11 50.4(2) . . . . ?
C4 C3 C7 C11 -127.74(14) . . . . ?
C2 C3 C7 C8 174.18(17) . . . . ?
C4 C3 C7 C8 -3.94(16) . . . . ?
C4 N1 C8 O1 175.04(18) . . . . ?
C9 N1 C8 O1 5.5(3) . . . . ?
C4 N1 C8 C7 -7.22(19) . . . . ?
C9 N1 C8 C7 -176.76(19) . . . . ?
C3 C7 C8 O1 -175.61(17) . . . . ?
C10 C7 C8 O1 68.1(2) . . . . ?
C11 C7 C8 O1 -51.6(2) . . . . ?
C3 C7 C8 N1 6.65(16) . . . . ?
C10 C7 C8 N1 -109.61(15) . . . . ?
C11 C7 C8 N1 130.63(15) . . . . ?
C3 C7 C10 F3 66.90(18) . . . . ?
C11 C7 C10 F3 -58.86(18) . . . . ?
C8 C7 C10 F3 177.62(14) . . . . ?
C3 C7 C10 F2 -52.7(2) . . . . ?
C11 C7 C10 F2 -178.45(15) . . . . ?
C8 C7 C10 F2 58.0(2) . . . . ?
C3 C7 C10 F1 -173.20(14) . . . . ?
C11 C7 C10 F1 61.04(19) . . . . ?
C8 C7 C10 F1 -62.48(18) . . . . ?
C3 C7 C11 C12 70.17(16) . . . . ?
C10 C7 C11 C12 -166.41(14) . . . . ?
C8 C7 C11 C12 -47.01(18) . . . . ?
C7 C11 C12 O2 6.4(2) . . . . ?
C7 C11 C12 C13 -174.29(13) . . . . ?
O2 C12 C13 C14 -168.31(17) . . . . ?
C11 C12 C13 C14 12.4(2) . . . . ?
O2 C12 C13 C18 9.0(2) . . . . ?
C11 C12 C13 C18 -170.29(14) . . . . ?
C18 C13 C14 C15 -1.3(3) . . . . ?
C12 C13 C14 C15 175.98(17) . . . . ?
C13 C14 C15 C16 0.9(3) . . . . ?
C14 C15 C16 C17 0.3(3) . . . . ?
C15 C16 C17 C18 -1.2(3) . . . . ?
C16 C17 C18 C13 0.8(3) . . . . ?
C14 C13 C18 C17 0.4(3) . . . . ?
C12 C13 C18 C17 -176.91(16) . . . . ?

_refine_diff_density_max         0.457
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.166

