# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_exp_13717_auto
_database_code_depnum_ccdc_archive 'CCDC 2314640'
loop_
_audit_author_name
_audit_author_address
Yuanxia
;China West Normal University
China
;
_audit_update_record             
;
2023-12-15 deposited with the CCDC.	2024-07-31 downloaded from the CCDC.
;
_audit_creation_date             2023-12-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H9 F4 N O'
_chemical_formula_sum            'C16 H9 F4 N O'
_chemical_formula_weight         307.24
_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 0.0033 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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   16.1519(17)
_cell_length_b                   9.9600(11)
_cell_length_c                   8.6943(9)
_cell_angle_alpha                90
_cell_angle_beta                 98.929(10)
_cell_angle_gamma                90
_cell_volume                     1381.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1299
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.4740
_cell_measurement_theta_min      3.1240
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90365
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.99a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0632
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.855
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6389
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.855
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.151
_diffrn_reflns_theta_min         2.411
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.855
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -16.00  78.00   1.00    5.00    --   16.96  19.00 150.00   94
  2  ω    -39.00  -9.00   1.00    5.00    --  -17.28 -77.00 -90.00   30
  3  ω    -73.00 -44.00   1.00    5.00    --  -17.28 137.00  53.00   29
  4  ω    -12.00  18.00   1.00    5.00    --  -17.28  77.00-150.00   30
  5  ω    -31.00  11.00   1.00    5.00    --  -17.28 -77.00 -30.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0159032000
_diffrn_orient_matrix_UB_12      0.0657424000
_diffrn_orient_matrix_UB_13      0.0069824000
_diffrn_orient_matrix_UB_21      0.0392226000
_diffrn_orient_matrix_UB_22      0.0273371000
_diffrn_orient_matrix_UB_23      -0.0108005000
_diffrn_orient_matrix_UB_31      -0.0135549000
_diffrn_orient_matrix_UB_32      0.0020357000
_diffrn_orient_matrix_UB_33      -0.0815874000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1702
_reflns_number_total             3175
_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 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1344
_refine_ls_R_factor_gt           0.0643
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0365P)²+0.2360P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1341
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H),
 C00J(H00J), C00L(H00L), C00M(H00M)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O001 O 0.82975(10) 0.6371(2) 0.8626(2) 0.0709(6) Uani 1 1 d . . . . .
F002 F 0.75406(12) 0.22765(19) 0.3008(2) 0.0981(6) Uani 1 1 d . . . . .
N003 N 0.76338(12) 0.5591(2) 0.6259(2) 0.0494(5) Uani 1 1 d . . . . .
F004 F 0.79551(13) 0.3901(2) 0.1751(2) 0.1091(7) Uani 1 1 d . . . . .
F005 F 0.66487(12) 0.3452(2) 0.1537(2) 0.1250(9) Uani 1 1 d . . . . .
F006 F 0.46316(12) 0.8204(2) 0.6253(2) 0.1294(9) Uani 1 1 d . . . . .
C007 C 0.89731(14) 0.4866(2) 0.6999(2) 0.0456(6) Uani 1 1 d . . . . .
C008 C 0.78083(15) 0.4703(2) 0.5081(3) 0.0463(6) Uani 1 1 d . . . . .
C009 C 0.86809(14) 0.4245(2) 0.5589(2) 0.0438(6) Uani 1 1 d . . . . .
C00A C 0.68514(16) 0.6262(3) 0.6244(3) 0.0500(6) Uani 1 1 d . . . . .
C00B C 0.83028(15) 0.5703(3) 0.7456(3) 0.0517(6) Uani 1 1 d . . . . .
C00C C 0.92015(16) 0.3398(2) 0.4923(3) 0.0528(7) Uani 1 1 d . . . . .
H00C H 0.901448 0.297052 0.398211 0.063 Uiso 1 1 calc R U . . .
C00D C 0.97815(16) 0.4679(3) 0.7753(3) 0.0557(7) Uani 1 1 d . . . . .
H00D H 0.997322 0.511355 0.868720 0.067 Uiso 1 1 calc R U . . .
C00E C 1.02964(16) 0.3829(3) 0.7082(3) 0.0597(7) Uani 1 1 d . . . . .
H00E H 1.084228 0.367893 0.757258 0.072 Uiso 1 1 calc R U . . .
C00F C 1.00093(16) 0.3201(3) 0.5692(3) 0.0573(7) Uani 1 1 d . . . . .
H00F H 1.036640 0.263040 0.525881 0.069 Uiso 1 1 calc R U . . .
C00G C 0.72452(16) 0.4448(3) 0.3831(3) 0.0605(7) Uani 1 1 d . . . . .
H00G H 0.673431 0.489261 0.375813 0.073 Uiso 1 1 calc R U . . .
C00H C 0.61921(18) 0.5602(3) 0.6708(3) 0.0750(9) Uani 1 1 d . . . . .
H00H H 0.625319 0.471277 0.703110 0.090 Uiso 1 1 calc R U . . .
C00I C 0.7352(2) 0.3533(3) 0.2553(4) 0.0752(9) Uani 1 1 d . . . . .
C00J C 0.67681(19) 0.7572(3) 0.5765(3) 0.0706(8) Uani 1 1 d . . . . .
H00J H 0.721527 0.801745 0.543507 0.085 Uiso 1 1 calc R U . . .
C00K C 0.5371(2) 0.7547(4) 0.6243(4) 0.0811(10) Uani 1 1 d . . . . .
C00L C 0.6011(2) 0.8230(3) 0.5776(4) 0.0854(10) Uani 1 1 d . . . . .
H00L H 0.594583 0.912275 0.546729 0.102 Uiso 1 1 calc R U . . .
C00M C 0.5433(2) 0.6249(4) 0.6703(4) 0.0893(10) Uani 1 1 d . . . . .
H00M H 0.497824 0.580394 0.700583 0.107 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
O001 C00B 1.217(3) . ?
F002 C00I 1.333(3) . ?
N003 C008 1.414(3) . ?
N003 C00A 1.428(3) . ?
N003 C00B 1.383(3) . ?
F004 C00I 1.335(4) . ?
F005 C00I 1.328(3) . ?
F006 C00K 1.363(3) . ?
C007 C009 1.388(3) . ?
C007 C00B 1.469(3) . ?
C007 C00D 1.380(3) . ?
C008 C009 1.482(3) . ?
C008 C00G 1.330(3) . ?
C009 C00C 1.380(3) . ?
C00A C00H 1.365(3) . ?
C00A C00J 1.370(4) . ?
C00C H00C 0.9300 . ?
C00C C00F 1.385(3) . ?
C00D H00D 0.9300 . ?
C00D C00E 1.378(3) . ?
C00E H00E 0.9300 . ?
C00E C00F 1.376(3) . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00G C00I 1.467(4) . ?
C00H H00H 0.9300 . ?
C00H C00M 1.385(4) . ?
C00J H00J 0.9300 . ?
C00J C00L 1.388(4) . ?
C00K C00L 1.352(4) . ?
C00K C00M 1.352(5) . ?
C00L H00L 0.9300 . ?
C00M H00M 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
C008 N003 C00A 124.17(19) . . ?
C00B N003 C008 112.0(2) . . ?
C00B N003 C00A 123.78(19) . . ?
C009 C007 C00B 109.1(2) . . ?
C00D C007 C009 121.8(2) . . ?
C00D C007 C00B 129.1(2) . . ?
N003 C008 C009 105.32(19) . . ?
C00G C008 N003 121.6(2) . . ?
C00G C008 C009 133.1(2) . . ?
C007 C009 C008 107.6(2) . . ?
C00C C009 C007 119.8(2) . . ?
C00C C009 C008 132.6(2) . . ?
C00H C00A N003 120.1(2) . . ?
C00H C00A C00J 120.3(3) . . ?
C00J C00A N003 119.6(2) . . ?
O001 C00B N003 124.6(2) . . ?
O001 C00B C007 129.6(2) . . ?
N003 C00B C007 105.8(2) . . ?
C009 C00C H00C 120.9 . . ?
C009 C00C C00F 118.3(2) . . ?
C00F C00C H00C 120.9 . . ?
C007 C00D H00D 121.0 . . ?
C00E C00D C007 118.1(2) . . ?
C00E C00D H00D 121.0 . . ?
C00D C00E H00E 119.7 . . ?
C00F C00E C00D 120.5(2) . . ?
C00F C00E H00E 119.7 . . ?
C00C C00F H00F 119.2 . . ?
C00E C00F C00C 121.6(3) . . ?
C00E C00F H00F 119.2 . . ?
C008 C00G H00G 116.8 . . ?
C008 C00G C00I 126.3(2) . . ?
C00I C00G H00G 116.8 . . ?
C00A C00H H00H 119.8 . . ?
C00A C00H C00M 120.4(3) . . ?
C00M C00H H00H 119.8 . . ?
F002 C00I F004 105.1(3) . . ?
F002 C00I C00G 114.0(3) . . ?
F004 C00I C00G 113.9(3) . . ?
F005 C00I F002 105.8(3) . . ?
F005 C00I F004 106.7(3) . . ?
F005 C00I C00G 110.6(3) . . ?
C00A C00J H00J 120.2 . . ?
C00A C00J C00L 119.5(3) . . ?
C00L C00J H00J 120.2 . . ?
C00L C00K F006 118.2(4) . . ?
C00M C00K F006 118.8(4) . . ?
C00M C00K C00L 123.0(3) . . ?
C00J C00L H00L 120.7 . . ?
C00K C00L C00J 118.7(3) . . ?
C00K C00L H00L 120.7 . . ?
C00H C00M H00M 121.0 . . ?
C00K C00M C00H 118.1(3) . . ?
C00K C00M H00M 121.0 . . ?

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
N003 C008 C009 C007 -0.1(3) . . . . ?
N003 C008 C009 C00C -178.7(2) . . . . ?
N003 C008 C00G C00I -179.0(3) . . . . ?
N003 C00A C00H C00M 179.7(2) . . . . ?
N003 C00A C00J C00L -178.9(2) . . . . ?
F006 C00K C00L C00J 179.8(3) . . . . ?
F006 C00K C00M C00H -179.0(3) . . . . ?
C007 C009 C00C C00F -0.3(3) . . . . ?
C007 C00D C00E C00F 0.6(4) . . . . ?
C008 N003 C00A C00H 80.7(3) . . . . ?
C008 N003 C00A C00J -99.6(3) . . . . ?
C008 N003 C00B O001 -177.5(2) . . . . ?
C008 N003 C00B C007 2.2(3) . . . . ?
C008 C009 C00C C00F 178.2(2) . . . . ?
C008 C00G C00I F002 57.1(4) . . . . ?
C008 C00G C00I F004 -63.6(4) . . . . ?
C008 C00G C00I F005 176.2(3) . . . . ?
C009 C007 C00B O001 177.4(3) . . . . ?
C009 C007 C00B N003 -2.2(3) . . . . ?
C009 C007 C00D C00E -1.2(4) . . . . ?
C009 C008 C00G C00I 2.2(5) . . . . ?
C009 C00C C00F C00E -0.2(4) . . . . ?
C00A N003 C008 C009 -179.5(2) . . . . ?
C00A N003 C008 C00G 1.4(4) . . . . ?
C00A N003 C00B O001 0.7(4) . . . . ?
C00A N003 C00B C007 -179.7(2) . . . . ?
C00A C00H C00M C00K -0.8(5) . . . . ?
C00A C00J C00L C00K -0.8(4) . . . . ?
C00B N003 C008 C009 -1.3(3) . . . . ?
C00B N003 C008 C00G 179.6(2) . . . . ?
C00B N003 C00A C00H -97.3(3) . . . . ?
C00B N003 C00A C00J 82.5(3) . . . . ?
C00B C007 C009 C008 1.4(3) . . . . ?
C00B C007 C009 C00C -179.8(2) . . . . ?
C00B C007 C00D C00E 179.8(2) . . . . ?
C00D C007 C009 C008 -177.8(2) . . . . ?
C00D C007 C009 C00C 1.0(3) . . . . ?
C00D C007 C00B O001 -3.4(4) . . . . ?
C00D C007 C00B N003 176.9(2) . . . . ?
C00D C00E C00F C00C 0.1(4) . . . . ?
C00G C008 C009 C007 178.8(3) . . . . ?
C00G C008 C009 C00C 0.2(5) . . . . ?
C00H C00A C00J C00L 0.9(4) . . . . ?
C00J C00A C00H C00M -0.1(4) . . . . ?
C00L C00K C00M C00H 0.8(5) . . . . ?
C00M C00K C00L C00J 0.0(5) . . . . ?

_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 1.090
_oxdiff_exptl_absorpt_empirical_full_min 0.839
