# Supplementary Information (SI) for RSC Advances.
# 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_T
_database_code_depnum_ccdc_archive 'CCDC 2373595'
loop_
_audit_author_name
_audit_author_address
'xiaoyu xie'
;HuaiBei Normal University
China
;
_audit_update_record             
;
2024-07-26 deposited with the CCDC.	2025-08-17 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         'C16 H14 F N O2'
_chemical_formula_sum            'C16 H14 F N O2'
_chemical_formula_weight         271.28

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   7.3027(15)
_cell_length_b                   10.689(2)
_cell_length_c                   17.559(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1370.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    58006
_cell_measurement_theta_min      3.573
_cell_measurement_theta_max      27.557

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            58006
_diffrn_reflns_av_unetI/netI     0.0092
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.573
_diffrn_reflns_theta_max         27.557
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3164
_reflns_number_gt                2928
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.999

_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    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Diamond
_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)+(0.0742P)²+0.0963P] 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-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.077(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1218 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(12)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3164
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0325
_refine_ls_wR_factor_ref         0.1054
_refine_ls_wR_factor_gt          0.0977
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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 0.31943(19) 0.59316(13) 0.51023(7) 0.0644(4) Uani 1 1 d . . . . .
O1 O 0.29045(16) 0.66286(13) 0.34292(8) 0.0483(3) Uani 1 1 d . . . . .
O2 O 0.91016(18) 0.34969(13) 0.23590(9) 0.0543(4) Uani 1 1 d . . . . .
H2 H 0.8610 0.2808 0.2334 0.081 Uiso 1 1 calc R U . . .
N1 N 0.58672(19) 0.66989(13) 0.29531(8) 0.0390(3) Uani 1 1 d . . . . .
C1 C 0.5596(2) 0.62206(14) 0.42083(9) 0.0387(4) Uani 1 1 d . . . . .
C2 C 0.5007(3) 0.59541(17) 0.49400(10) 0.0476(4) Uani 1 1 d . . . . .
C3 C 0.6256(4) 0.5698(2) 0.55064(11) 0.0627(6) Uani 1 1 d . . . . .
H3 H 0.5862 0.5519 0.5998 0.075 Uiso 1 1 calc R U . . .
C4 C 0.8112(4) 0.5711(2) 0.53333(12) 0.0671(6) Uani 1 1 d . . . . .
H4 H 0.8953 0.5536 0.5717 0.080 Uiso 1 1 calc R U . . .
C5 C 0.8751(3) 0.5977(2) 0.46074(12) 0.0564(5) Uani 1 1 d . . . . .
H5 H 0.9997 0.5983 0.4498 0.068 Uiso 1 1 calc R U . . .
C6 C 0.7459(2) 0.62318(15) 0.40539(10) 0.0414(4) Uani 1 1 d . . . . .
C7 C 0.5483(2) 0.69992(15) 0.21805(10) 0.0415(4) Uani 1 1 d . . . . .
C8 C 0.4023(3) 0.64371(18) 0.18047(11) 0.0500(4) Uani 1 1 d . . . . .
H8 H 0.3289 0.5857 0.2055 0.060 Uiso 1 1 calc R U . . .
C9 C 0.3672(4) 0.6751(2) 0.10500(12) 0.0653(6) Uani 1 1 d . . . . .
H9 H 0.2681 0.6392 0.0800 0.078 Uiso 1 1 calc R U . . .
C10 C 0.4774(4) 0.7587(3) 0.06701(13) 0.0733(7) Uani 1 1 d . . . . .
H10 H 0.4539 0.7784 0.0164 0.088 Uiso 1 1 calc R U . . .
C11 C 0.6224(4) 0.8129(2) 0.10423(13) 0.0675(6) Uani 1 1 d . . . . .
H11 H 0.6965 0.8697 0.0786 0.081 Uiso 1 1 calc R U . . .
C12 C 0.6598(3) 0.78398(19) 0.17968(12) 0.0538(5) Uani 1 1 d . . . . .
H12 H 0.7588 0.8207 0.2044 0.065 Uiso 1 1 calc R U . . .
C13 C 0.4576(2) 0.65278(15) 0.35086(9) 0.0371(3) Uani 1 1 d . . . . .
C14 C 0.7772(2) 0.65610(16) 0.32322(10) 0.0398(4) Uani 1 1 d . . . . .
H14 H 0.8393 0.7372 0.3202 0.048 Uiso 1 1 calc R U . . .
C15 C 0.8861(2) 0.55964(16) 0.27797(10) 0.0426(4) Uani 1 1 d . . . . .
H15A H 0.9056 0.5911 0.2268 0.051 Uiso 1 1 calc R U . . .
H15B H 1.0052 0.5490 0.3016 0.051 Uiso 1 1 calc R U . . .
C16 C 0.7927(3) 0.43407(18) 0.27326(13) 0.0519(5) Uani 1 1 d . . . . .
H16A H 0.7650 0.4037 0.3240 0.062 Uiso 1 1 calc R U . . .
H16B H 0.6786 0.4417 0.2453 0.062 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 C2 1.354(2) . ?
O1 C13 1.2334(19) . ?
O2 C16 1.407(2) . ?
N1 C13 1.369(2) . ?
N1 C7 1.422(2) . ?
N1 C14 1.482(2) . ?
C1 C2 1.385(3) . ?
C1 C6 1.387(2) . ?
C1 C13 1.474(2) . ?
C2 C3 1.377(3) . ?
C3 C4 1.389(4) . ?
C4 C5 1.387(3) . ?
C5 C6 1.382(2) . ?
C6 C14 1.503(2) . ?
C7 C12 1.387(3) . ?
C7 C8 1.390(3) . ?
C8 C9 1.391(3) . ?
C9 C10 1.375(4) . ?
C10 C11 1.372(4) . ?
C11 C12 1.388(3) . ?
C14 C15 1.525(2) . ?
C15 C16 1.508(2) . ?

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
C13 N1 C7 125.04(14) . . ?
C13 N1 C14 113.42(13) . . ?
C7 N1 C14 121.54(14) . . ?
C2 C1 C6 119.23(16) . . ?
C2 C1 C13 131.45(16) . . ?
C6 C1 C13 109.32(14) . . ?
F1 C2 C3 119.48(18) . . ?
F1 C2 C1 120.20(17) . . ?
C3 C2 C1 120.32(19) . . ?
C2 C3 C4 119.1(2) . . ?
C5 C4 C3 122.12(19) . . ?
C6 C5 C4 117.2(2) . . ?
C5 C6 C1 122.04(18) . . ?
C5 C6 C14 128.15(17) . . ?
C1 C6 C14 109.80(14) . . ?
C12 C7 C8 119.96(17) . . ?
C12 C7 N1 119.60(17) . . ?
C8 C7 N1 120.43(16) . . ?
C7 C8 C9 119.3(2) . . ?
C10 C9 C8 120.7(2) . . ?
C11 C10 C9 119.7(2) . . ?
C10 C11 C12 120.8(2) . . ?
C11 C12 C7 119.5(2) . . ?
O1 C13 N1 126.12(15) . . ?
O1 C13 C1 127.88(15) . . ?
N1 C13 C1 105.99(13) . . ?
N1 C14 C6 101.43(13) . . ?
N1 C14 C15 112.60(13) . . ?
C6 C14 C15 114.90(14) . . ?
C16 C15 C14 113.22(14) . . ?
O2 C16 C15 108.67(14) . . ?

_refine_diff_density_max         0.191
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.066

