# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_zhou_f_auto
_database_code_depnum_ccdc_archive 'CCDC 2539928'
loop_
_audit_author_name
_audit_author_address
'Long-Yong Xie'
;Hunan university of science and engineering
China
;
_audit_update_record             
;
2026-03-23 deposited with the CCDC.	2026-05-29 downloaded from the CCDC.
;
_audit_creation_date             2025-10-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        1
_chemical_formula_moiety         'C18 H14 F2 N2 O'
_chemical_formula_sum            'C18 H14 F2 N2 O'
_chemical_formula_weight         312.31
_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 0.0181 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'
F F 0.0727 0.0534 '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'

_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      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   12.29858(14)
_cell_length_b                   18.4524(2)
_cell_length_c                   12.77536(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2899.22(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    12390
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      74.9060
_cell_measurement_theta_min      2.3860
_shelx_estimated_absorpt_T_max   0.899
_shelx_estimated_absorpt_T_min   0.869
_exptl_absorpt_coefficient_mu    0.903
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0139
_diffrn_reflns_av_unetI/netI     0.0081
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15173
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.798
_diffrn_reflns_theta_min         4.320
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    129.00 155.00   0.50    0.05    --  107.57  94.00  59.00   52
  2  ω    112.00 175.00   0.50    0.05    --  107.57 128.00 133.00  126
  3  ω    103.00 136.00   0.50    0.05    --  107.57  15.00  60.00   66
  4  ω    100.00 138.00   0.50    0.05    --  107.57  15.00   0.00   76
  5  ω     94.00 132.00   0.50    0.05    --  107.57  15.00-180.00   76
  6  ω     44.00  70.00   0.50    0.05    --  107.57 -77.00-180.00   52
  7  ω     34.00  72.00   0.50    0.05    --  107.57 -77.00 -90.00   76
  8  ω     37.00  63.00   0.50    0.05    --  107.57 -77.00 -30.00   52
  9  ω     37.00  78.00   0.50    0.05    --  107.57 -77.00  30.00   82
 10  ω     43.00  76.00   0.50    0.05    --  107.57 -77.00 150.00   66
 11  ω    -35.00   9.00   0.50    0.05    --   43.18 -30.00 113.00   88
 12  ω     37.00  67.00   0.50    0.05    --  107.57-126.00   0.00   60
 13  ω     56.00  84.00   0.50    0.05    --  107.57 -95.00 -30.00   56
 14  ω    -13.00  32.00   0.50    0.05    --  -43.18  38.00 -60.00   90
 15  ω     -8.00  29.00   0.50    0.05    --  -43.18  38.00 -30.00   74
 16  ω     -5.00  29.00   0.50    0.05    --  -43.18  38.00  30.00   68
 17  ω    -42.00   0.00   0.50    0.05    --  -43.18  57.00  60.00   84
 18  ω    -92.00 -12.00   0.50    0.05    --  -43.18 128.00 133.00  160
 19  ω    -83.00 -31.00   0.50    0.05    -- -103.00 128.00 133.00  104
 20  ω    -65.00 -34.00   0.50    0.05    -- -103.00  77.00 120.00   62
 21  ω    -92.00 -29.00   0.50    0.05    -- -103.00  94.00  59.00  126
 22  ω    -70.00 -37.00   0.50    0.05    -- -103.00  77.00 -90.00   66
 23  ω   -163.00 -89.00   0.50    0.05    -- -103.00 -30.00 113.00  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0122179000
_diffrn_orient_matrix_UB_12      0.0770455000
_diffrn_orient_matrix_UB_13      -0.0449531000
_diffrn_orient_matrix_UB_21      0.1244909000
_diffrn_orient_matrix_UB_22      0.0057318000
_diffrn_orient_matrix_UB_23      -0.0109236000
_diffrn_orient_matrix_UB_31      -0.0072692000
_diffrn_orient_matrix_UB_32      -0.0316717000
_diffrn_orient_matrix_UB_33      -0.1113083000
_diffrn_oxdiff_digest_frames     
;
01b58cccd0177069ca1ffd70ad020e68c60191065d2
;
_diffrn_oxdiff_digest_hkl        
;
01fcb21353740dface4bd928507cf4f435d721
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2844
_reflns_number_total             2909
_reflns_odcompleteness_completeness 99.29
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.143a 64-bit (release 25-10-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2909
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0367
_refine_ls_restrained_S_all      1.088
_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)+(0.0461P)²+1.1380P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.0976
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H7A,H7B,H7C} of C7
 At 1.5 times of:
  {H11A,H11B,H11C} of C11
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C12(H12), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
F1 F 0.85696(6) 0.46115(4) 0.51016(7) 0.0412(2) Uani 1 1 d . . . . .
F2 F 0.78487(6) 0.38022(5) 0.35100(7) 0.0465(2) Uani 1 1 d . . . . .
O1 O 0.33094(7) 0.45780(5) 0.73129(7) 0.0338(2) Uani 1 1 d . . . . .
N1 N 0.43032(8) 0.37531(5) 0.49763(7) 0.0233(2) Uani 1 1 d . . . . .
N2 N 0.50170(8) 0.46047(5) 0.66428(7) 0.0234(2) Uani 1 1 d . . . . .
C1 C 0.71406(10) 0.39915(7) 0.42719(10) 0.0309(3) Uani 1 1 d . . . . .
C2 C 0.75156(10) 0.44086(7) 0.51002(10) 0.0296(3) Uani 1 1 d . . . . .
C3 C 0.68492(10) 0.46175(6) 0.59051(10) 0.0269(3) Uani 1 1 d . . . . .
H3 H 0.712111 0.489785 0.647118 0.032 Uiso 1 1 calc R . . . .
C4 C 0.57530(9) 0.44055(6) 0.58700(9) 0.0221(2) Uani 1 1 d . . . . .
C5 C 0.53672(9) 0.39834(6) 0.50355(9) 0.0227(2) Uani 1 1 d . . . . .
C6 C 0.60813(10) 0.37752(7) 0.42297(10) 0.0284(3) Uani 1 1 d . . . . .
H6 H 0.582871 0.348738 0.366304 0.034 Uiso 1 1 calc R . . . .
C7 C 0.53671(11) 0.50857(8) 0.74944(10) 0.0341(3) Uani 1 1 d . . . . .
H7A H 0.568386 0.552774 0.719805 0.041 Uiso 1 1 calc GR . . . .
H7B H 0.591206 0.483763 0.792426 0.041 Uiso 1 1 calc GR . . . .
H7C H 0.473884 0.521273 0.792916 0.041 Uiso 1 1 calc GR . . . .
C8 C 0.39465(9) 0.43820(6) 0.66303(9) 0.0228(2) Uani 1 1 d . . . . .
C9 C 0.36307(9) 0.39133(6) 0.57258(8) 0.0208(2) Uani 1 1 d . . . . .
C10 C 0.25084(9) 0.36226(6) 0.56472(8) 0.0224(2) Uani 1 1 d . . . . .
C11 C 0.21148(11) 0.34644(8) 0.45563(10) 0.0360(3) Uani 1 1 d . . . . .
H11A H 0.175364 0.389467 0.427107 0.054 Uiso 1 1 calc GR . . . .
H11B H 0.159933 0.305965 0.457521 0.054 Uiso 1 1 calc GR . . . .
H11C H 0.273501 0.333592 0.411189 0.054 Uiso 1 1 calc GR . . . .
C12 C 0.19551(9) 0.34481(6) 0.65158(9) 0.0233(2) Uani 1 1 d . . . . .
H12 H 0.228668 0.357904 0.716025 0.028 Uiso 1 1 calc R . . . .
C13 C 0.08954(9) 0.30782(6) 0.65942(9) 0.0229(2) Uani 1 1 d . . . . .
C14 C 0.00217(10) 0.31962(7) 0.59195(10) 0.0296(3) Uani 1 1 d . . . . .
H14 H 0.008732 0.354083 0.537071 0.036 Uiso 1 1 calc R . . . .
C15 C -0.09441(10) 0.28144(7) 0.60424(12) 0.0351(3) Uani 1 1 d . . . . .
H15 H -0.153283 0.290141 0.557761 0.042 Uiso 1 1 calc R . . . .
C16 C -0.10567(10) 0.23086(7) 0.68354(11) 0.0319(3) Uani 1 1 d . . . . .
H16 H -0.171233 0.204067 0.690481 0.038 Uiso 1 1 calc R . . . .
C17 C -0.02063(10) 0.21966(7) 0.75261(10) 0.0296(3) Uani 1 1 d . . . . .
H17 H -0.027988 0.185562 0.807880 0.035 Uiso 1 1 calc R . . . .
C18 C 0.07522(9) 0.25825(7) 0.74101(9) 0.0262(3) Uani 1 1 d . . . . .
H18 H 0.132590 0.250845 0.789648 0.031 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
F1 C2 1.3491(14) . ?
F2 C1 1.3519(14) . ?
O1 C8 1.2268(14) . ?
N1 C5 1.3780(15) . ?
N1 C9 1.2994(14) . ?
N2 C4 1.3890(15) . ?
N2 C7 1.4686(15) . ?
N2 C8 1.3793(15) . ?
C1 C2 1.3875(19) . ?
C1 C6 1.3637(17) . ?
C2 C3 1.3702(18) . ?
C3 H3 0.9500 . ?
C3 C4 1.4044(16) . ?
C4 C5 1.4030(16) . ?
C5 C6 1.4066(16) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.4947(15) . ?
C9 C10 1.4843(15) . ?
C10 C11 1.5038(16) . ?
C10 C12 1.3410(16) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12 0.9500 . ?
C12 C13 1.4746(15) . ?
C13 C14 1.3946(16) . ?
C13 C18 1.3980(16) . ?
C14 H14 0.9500 . ?
C14 C15 1.3900(17) . ?
C15 H15 0.9500 . ?
C15 C16 1.3844(19) . ?
C16 H16 0.9500 . ?
C16 C17 1.3839(18) . ?
C17 H17 0.9500 . ?
C17 C18 1.3852(16) . ?
C18 H18 0.9500 . ?

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
C9 N1 C5 119.59(10) . . ?
C4 N2 C7 119.71(10) . . ?
C8 N2 C4 122.34(9) . . ?
C8 N2 C7 117.93(10) . . ?
F2 C1 C2 118.58(11) . . ?
F2 C1 C6 120.75(12) . . ?
C6 C1 C2 120.67(11) . . ?
F1 C2 C1 118.31(11) . . ?
F1 C2 C3 119.72(11) . . ?
C3 C2 C1 121.97(11) . . ?
C2 C3 H3 120.9 . . ?
C2 C3 C4 118.15(11) . . ?
C4 C3 H3 120.9 . . ?
N2 C4 C3 121.95(10) . . ?
N2 C4 C5 117.82(10) . . ?
C5 C4 C3 120.24(10) . . ?
N1 C5 C4 122.28(10) . . ?
N1 C5 C6 117.94(10) . . ?
C4 C5 C6 119.77(11) . . ?
C1 C6 C5 119.18(11) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C8 N2 120.90(10) . . ?
O1 C8 C9 123.65(10) . . ?
N2 C8 C9 115.43(9) . . ?
N1 C9 C8 122.41(10) . . ?
N1 C9 C10 117.37(10) . . ?
C10 C9 C8 120.21(9) . . ?
C9 C10 C11 115.61(10) . . ?
C12 C10 C9 120.18(10) . . ?
C12 C10 C11 123.84(11) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12 116.0 . . ?
C10 C12 C13 128.01(10) . . ?
C13 C12 H12 116.0 . . ?
C14 C13 C12 124.52(10) . . ?
C14 C13 C18 117.77(11) . . ?
C18 C13 C12 117.70(10) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.63(12) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.65(12) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 120.3 . . ?
C17 C16 C15 119.46(11) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.88(11) . . ?
C18 C17 H17 120.1 . . ?
C13 C18 H18 119.2 . . ?
C17 C18 C13 121.56(11) . . ?
C17 C18 H18 119.2 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.232
_oxdiff_exptl_absorpt_empirical_full_min 0.769
