# 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_liangxinan-lxa-20200622-250k
_database_code_depnum_ccdc_archive 'CCDC 2422837'
loop_
_audit_author_name
_audit_author_address
'Xing-An Liang'
;Wuhan university
China
;
_audit_update_record             
;
2025-02-09 deposited with the CCDC.	2025-06-25 downloaded from the CCDC.
;
_audit_creation_date             2020-06-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H13 Cl F N O'
_chemical_formula_sum            'C15 H13 Cl F N O'
_chemical_formula_weight         277.71
_chemical_melting_point          ?
_chemical_oxdiff_formula         'H C N O F'
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'
Cl Cl 0.3639 0.7018 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.1084(2)
_cell_length_b                   10.9354(3)
_cell_length_c                   12.2655(4)
_cell_angle_alpha                80.540(3)
_cell_angle_beta                 87.394(3)
_cell_angle_gamma                81.359(2)
_cell_volume                     668.04(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4430
_cell_measurement_temperature    249.99(10)
_cell_measurement_theta_max      70.7110
_cell_measurement_theta_min      3.6270
_shelx_estimated_absorpt_T_max   0.927
_shelx_estimated_absorpt_T_min   0.821
_exptl_absorpt_coefficient_mu    2.566
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11194
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        64.995
_diffrn_reflns_theta_max         64.995
_diffrn_reflns_theta_min         3.654
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      249.99(10)
_diffrn_detector                 'Hybrid Pixel Counting (HPC) detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HyPix-6000HE'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -82.00  43.00   0.50    0.50    --    5.00 -38.00-150.00  250
  2  ω    -46.00 -20.00   0.50    0.50    --  -47.30 -57.00 -30.00   52
  3  ω    -84.00  37.00   0.50    0.50    --  -47.30  38.00  90.00  242
  4  ω   -117.00 -83.00   0.50    0.50    --  -47.30 -57.00 -30.00   68
  5  ω    -66.00  -8.00   0.50    0.50    --  -47.30 -75.00-180.00  116
  6  ω   -120.00 -82.00   0.50    0.50    --  -47.30 -75.00-180.00   76
  7  ω    -90.00  -9.00   0.50    0.50    --  -47.30 -75.00  30.00  162
  8  ω    -60.00 -29.00   0.50    0.50    --  -68.00 -75.00 -37.76   62
  9  ω    -64.00 -38.00   0.50    0.71    --  -76.00 -75.00 121.76   52
 10  ω    -71.00 -40.00   0.50    0.71    --  -76.00 -72.00  51.68   62
 11  ω    -66.00 -37.00   0.50    0.71    --  -76.00 -75.00 151.99   58
 12  ω    -69.00 -43.00   0.50    0.71    --  -80.00 -70.00  77.75   52
 13  ω    -73.00 -42.00   0.50    0.71    --  -80.00 -74.00 -73.36   62
 14  ω   -130.00-104.00   0.50    0.71    --  -80.00 -74.00 -73.36   52
 15  ω    -77.00 -48.00   0.50    0.71    --  -84.00 -68.00   2.47   58
 16  ω   -151.00-112.00   0.50    0.71    --  -84.00 -68.00   2.47   78
 17  ω   -170.00-138.00   0.50    0.71    --  -88.00 -73.00 -23.01   64
 18  ω   -113.00 -87.00   0.50    0.71    --  -88.00 -60.00-152.22   52
 19  ω   -140.00 -54.00   0.50    0.71    --  -88.00 -61.00-120.01  172
 20  ω   -121.00 -61.00   0.50    0.71    --  -88.00 -63.00 108.81  120
 21  ω   -169.00 -50.00   0.50    0.71    --  -88.00 -75.00 -36.39  238
 22  ω   -176.00-146.00   0.50    0.71    --  -88.00 -61.00-120.01   60
 23  ω    -83.00 -50.00   0.50    0.71    --  -88.00 -73.00 -23.01   66
 24  ω   -131.00 -86.00   0.50    0.71    --  -88.00 -73.00 -23.01   90
 25  ω    -81.00 -54.00   0.50    0.71    --  -88.00 -60.00-152.22   54
 26  ω    -97.00 -60.00   0.50    0.71    --  -92.00 -57.00-170.22   74
 27  ω   -181.00-103.00   0.50    0.71    --  -92.00 -57.00-170.22  156
 28  ω   -185.00 -62.00   0.50    0.71    --  -96.70 -57.00 120.00  246
 29  ω   -128.00 -59.00   0.50    0.71    --  -96.70  75.00-180.00  138
 30  ω   -132.00 -46.00   0.50    0.71    --  -96.70  75.00 -30.00  172
 31  ω   -185.00 -64.00   0.50    0.71    --  -96.70 -57.00  30.00  242
 32  ω   -181.00 -60.00   0.50    0.71    --  -96.70 -75.00 -68.24  242
 33  ω    -67.00 -42.00   0.50    0.71    --  -96.70  75.00  90.00   50
 34  ω   -107.00 -78.00   0.50    0.71    --  -96.70  75.00  90.00   58
 35  ω    -53.00  -7.00   0.50    0.71    --  -96.70  75.00 -90.00   92
 36  ω   -132.00 -62.00   0.50    0.71    --  -96.70  75.00 -90.00  140
 37  ω   -131.00 -13.00   0.50    0.71    --  -96.70  75.00  30.00  236
 38  ω   -105.00 -57.00   0.50    0.71    --  -96.70 -75.00-180.00   96
 39  ω   -150.00-109.00   0.50    0.71    --  -96.70 -75.00-180.00   82
 40  ω   -179.00 -62.00   0.50    0.71    --  -96.70 -56.00  53.97  234
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'profile data from ω-scans and φ-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0031882000
_diffrn_orient_matrix_UB_12      0.0340235000
_diffrn_orient_matrix_UB_13      -0.1269770000
_diffrn_orient_matrix_UB_21      -0.0396119000
_diffrn_orient_matrix_UB_22      -0.1347192000
_diffrn_orient_matrix_UB_23      -0.0095352000
_diffrn_orient_matrix_UB_31      -0.3025051000
_diffrn_orient_matrix_UB_32      0.0390936000
_diffrn_orient_matrix_UB_33      0.0026470000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'VariMax VHF'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_target            Cu
_diffrn_source_type              'Rigaku MicroMax-007HF'
_diffrn_source_voltage           40.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1934
_reflns_number_total             2248
_reflns_odcompleteness_completeness 99.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_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 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_computing_data_collection       
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_computing_data_reduction        
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.295
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0737
_refine_ls_restrained_S_all      1.083
_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)+(0.1149P)²+0.5755P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2100
_refine_ls_wR_factor_ref         0.2170
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C5(H5), C7(H7), C4(H4), C14(H14), C15(H15), C6(H6), C11(H11),
 C12(H12)
;
_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
Cl1 Cl 0.9724(2) 0.66280(8) 0.78501(9) 0.0734(4) Uani 1 1 d . . . . .
O1 O 0.3702(5) 0.6769(3) 0.5115(2) 0.0720(8) Uani 1 1 d . . . . .
F1 F 0.7962(8) 0.1058(3) 1.0186(3) 0.1215(12) Uani 1 1 d . . . . .
N1 N 0.8020(6) 0.6700(3) 0.5421(3) 0.0606(8) Uani 1 1 d . . . . .
H1 H 0.940173 0.706585 0.528115 0.073 Uiso 1 1 calc R . . . .
C1 C 0.5750(7) 0.7243(3) 0.4926(3) 0.0549(8) Uani 1 1 d . . . . .
C2 C 0.5837(6) 0.8422(3) 0.4128(3) 0.0533(8) Uani 1 1 d . . . . .
C3 C 0.7544(9) 0.9258(4) 0.4237(4) 0.0718(11) Uani 1 1 d . . . . .
H3 H 0.876341 0.906928 0.480258 0.086 Uiso 1 1 calc R . . . .
C5 C 0.5740(10) 1.0647(4) 0.2664(4) 0.0791(13) Uani 1 1 d . . . . .
H5 H 0.569680 1.139343 0.217236 0.095 Uiso 1 1 calc R . . . .
C8 C 0.8251(11) 0.5526(4) 0.6181(4) 0.0803(12) Uani 1 1 d . . . . .
H8A H 0.706964 0.500642 0.594726 0.096 Uiso 1 1 calc R . . . .
H8B H 1.004400 0.509510 0.612374 0.096 Uiso 1 1 calc R . . . .
C7 C 0.4112(9) 0.8704(4) 0.3269(4) 0.0771(11) Uani 1 1 d . . . . .
H7 H 0.295985 0.814872 0.317580 0.092 Uiso 1 1 calc R . . . .
C4 C 0.7457(10) 1.0376(4) 0.3511(4) 0.0816(12) Uani 1 1 d . . . . .
H4 H 0.858094 1.094347 0.360499 0.098 Uiso 1 1 calc R . . . .
C13 C 0.8015(10) 0.2154(4) 0.9485(4) 0.0805(12) Uani 1 1 d . . . . .
C10 C 0.7920(11) 0.4370(4) 0.8096(4) 0.0823(13) Uani 1 1 d . . . . .
C14 C 1.0029(11) 0.2238(4) 0.8742(4) 0.0866(13) Uani 1 1 d . . . . .
H14 H 1.136152 0.156595 0.869959 0.104 Uiso 1 1 calc R . . . .
C15 C 1.0026(11) 0.3386(5) 0.8032(4) 0.0893(14) Uani 1 1 d . . . . .
H15 H 1.140669 0.349736 0.752200 0.107 Uiso 1 1 calc R . . . .
C6 C 0.4083(11) 0.9820(5) 0.2538(4) 0.0905(14) Uani 1 1 d . . . . .
H6 H 0.291445 1.000284 0.195469 0.109 Uiso 1 1 calc R . . . .
C9 C 0.7661(10) 0.5630(4) 0.7327(4) 0.0816(12) Uani 1 1 d . . . . .
H9 H 0.581645 0.602579 0.737651 0.098 Uiso 1 1 calc R . . . .
C11 C 0.5969(12) 0.4205(4) 0.8855(4) 0.0892(14) Uani 1 1 d . . . . .
H11 H 0.458522 0.485279 0.890383 0.107 Uiso 1 1 calc R . . . .
C12 C 0.5999(11) 0.3101(5) 0.9552(4) 0.0911(14) Uani 1 1 d . . . . .
H12 H 0.464014 0.299497 1.007415 0.109 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
Cl1 C9 1.831(5) . ?
O1 C1 1.232(4) . ?
F1 C13 1.358(5) . ?
N1 H1 0.8600 . ?
N1 C1 1.344(5) . ?
N1 C8 1.450(5) . ?
C1 C2 1.490(5) . ?
C2 C3 1.380(5) . ?
C2 C7 1.371(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(6) . ?
C5 H5 0.9300 . ?
C5 C4 1.357(7) . ?
C5 C6 1.358(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.444(7) . ?
C7 H7 0.9300 . ?
C7 C6 1.388(6) . ?
C4 H4 0.9300 . ?
C13 C14 1.347(7) . ?
C13 C12 1.356(7) . ?
C10 C15 1.412(8) . ?
C10 C9 1.527(6) . ?
C10 C11 1.344(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.405(6) . ?
C15 H15 0.9300 . ?
C6 H6 0.9300 . ?
C9 H9 0.9800 . ?
C11 H11 0.9300 . ?
C11 C12 1.358(6) . ?
C12 H12 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
C1 N1 H1 118.4 . . ?
C1 N1 C8 123.1(3) . . ?
C8 N1 H1 118.4 . . ?
O1 C1 N1 121.0(3) . . ?
O1 C1 C2 121.9(3) . . ?
N1 C1 C2 117.2(3) . . ?
C3 C2 C1 122.5(3) . . ?
C7 C2 C1 118.8(3) . . ?
C7 C2 C3 118.6(4) . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.5(4) . . ?
C4 C3 H3 119.7 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.6(4) . . ?
C6 C5 H5 120.2 . . ?
N1 C8 H8A 108.4 . . ?
N1 C8 H8B 108.4 . . ?
H8A C8 H8B 107.4 . . ?
C9 C8 N1 115.6(4) . . ?
C9 C8 H8A 108.4 . . ?
C9 C8 H8B 108.4 . . ?
C2 C7 H7 120.0 . . ?
C2 C7 C6 120.0(4) . . ?
C6 C7 H7 120.0 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.3(4) . . ?
C5 C4 H4 119.8 . . ?
C14 C13 F1 118.5(4) . . ?
C14 C13 C12 123.2(4) . . ?
C12 C13 F1 118.2(4) . . ?
C15 C10 C9 123.9(5) . . ?
C11 C10 C15 119.4(4) . . ?
C11 C10 C9 116.7(4) . . ?
C13 C14 H14 121.5 . . ?
C13 C14 C15 117.0(5) . . ?
C15 C14 H14 121.5 . . ?
C10 C15 H15 120.1 . . ?
C14 C15 C10 119.8(5) . . ?
C14 C15 H15 120.1 . . ?
C5 C6 C7 120.9(4) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
Cl1 C9 H9 107.4 . . ?
C8 C9 Cl1 112.2(3) . . ?
C8 C9 C10 113.8(4) . . ?
C8 C9 H9 107.4 . . ?
C10 C9 Cl1 108.4(3) . . ?
C10 C9 H9 107.4 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.7(5) . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 119.9(5) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?

_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 1.358
_oxdiff_exptl_absorpt_empirical_full_min 0.733
