# 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_6
_database_code_depnum_ccdc_archive 'CCDC 2506020'
loop_
_audit_author_name
_audit_author_address
'Xuesen Fan'
;Henan Normal University
China
;
_audit_update_record             
;
2025-11-27 deposited with the CCDC.	2026-01-15 downloaded from the CCDC.
;
_audit_creation_date             2025-06-13
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H16 F3 N O2'
_chemical_formula_sum            'C21 H16 F3 N O2'
_chemical_formula_weight         371.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1 F1'
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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   7.3884(2)
_cell_length_b                   17.4100(4)
_cell_length_c                   27.1385(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3490.88(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4160
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.9500
_cell_measurement_theta_min      5.3340
_shelx_estimated_absorpt_T_max   0.910
_shelx_estimated_absorpt_T_min   0.832
_exptl_absorpt_coefficient_mu    0.956
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41396
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            8832
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.271
_diffrn_reflns_theta_min         5.081
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -12.00  14.00   1.00    1.00    --  -35.37 103.00  54.00   26
  2  ω    -78.00 -42.00   1.00    1.00    --  -35.37 154.00 110.00   36
  3  ω    101.00 160.00   1.00    3.72    --  106.81 120.00 -47.00   59
  4  ω    131.00 171.00   1.00    3.72    --  106.81  23.00-117.00   40
  5  ω     73.00  99.00   1.00    3.72    --  106.81-120.00-130.00   26
  6  ω    105.00 176.00   1.00    3.72    --  106.81 103.00  54.00   71
  7  ω   -102.00 -39.00   1.00    1.00    --  -35.37 -57.00-150.00   63
  8  ω     59.00 108.00   1.00    1.00    --   35.37-178.00  60.00   49
  9  ω    -11.00  34.00   1.00    1.00    --   35.37 -77.00  60.00   45
 10  ω     62.00 144.00   1.00    3.72    --  106.81 178.00 120.00   82
 11  ω     97.00 174.00   1.00    3.72    --  106.81  45.00 -60.00   77
 12  ω    131.00 156.00   1.00    3.72    --  106.81 111.00  90.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0030420000
_diffrn_orient_matrix_UB_12      -0.0255075000
_diffrn_orient_matrix_UB_13      -0.0543789000
_diffrn_orient_matrix_UB_21      0.2067966000
_diffrn_orient_matrix_UB_22      0.0101298000
_diffrn_orient_matrix_UB_23      -0.0028501000
_diffrn_orient_matrix_UB_31      0.0257166000
_diffrn_orient_matrix_UB_32      -0.0841234000
_diffrn_orient_matrix_UB_33      0.0161355000
_diffrn_oxdiff_digest_frames     
;
018a512e4c8ac7f68516dfc5232792a2b20002892ec
;
_diffrn_oxdiff_digest_hkl        
;
01bd5676e147a1a645a914049d12b6d2a44cdf
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2745
_reflns_number_total             3322
_reflns_odcompleteness_completeness 99.83
_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 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.197
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3322
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0641
_refine_ls_restrained_S_all      1.197
_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)+(0.0578P)²+2.7418P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1693
_refine_ls_wR_factor_ref         0.1750
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.0486(2) 0.42814(12) 0.57280(9) 0.0753(6) Uani 1 1 d . . . . .
F2 F 0.1954(3) 0.50458(15) 0.52618(8) 0.0870(8) Uani 1 1 d . . . . .
F3 F 0.1173(3) 0.54045(12) 0.59809(9) 0.0817(7) Uani 1 1 d . . . . .
O1 O 0.2580(4) 0.45169(13) 0.77016(8) 0.0680(7) Uani 1 1 d . . . . .
O2 O 0.4827(3) 0.50810(11) 0.58771(7) 0.0469(5) Uani 1 1 d . . . . .
N1 N 0.3080(3) 0.45260(12) 0.68750(8) 0.0431(5) Uani 1 1 d . . . . .
C1 C 0.3339(4) 0.41379(15) 0.64434(9) 0.0392(6) Uani 1 1 d . . . . .
C2 C 0.3567(4) 0.44771(15) 0.59219(9) 0.0401(6) Uani 1 1 d . . . . .
C3 C 0.4017(4) 0.37557(17) 0.56300(9) 0.0432(6) Uani 1 1 d . . . . .
C4 C 0.4530(4) 0.3694(2) 0.51411(10) 0.0560(8) Uani 1 1 d . . . . .
H4 H 0.4621 0.4127 0.4941 0.067 Uiso 1 1 calc R . . . .
C5 C 0.4904(5) 0.2968(2) 0.49584(12) 0.0677(10) Uani 1 1 d . . . . .
H5 H 0.5286 0.2915 0.4634 0.081 Uiso 1 1 calc R . . . .
C6 C 0.4720(5) 0.2327(2) 0.52476(13) 0.0689(10) Uani 1 1 d . . . . .
H6 H 0.4946 0.1845 0.5113 0.083 Uiso 1 1 calc R . . . .
C7 C 0.4203(5) 0.23861(19) 0.57377(11) 0.0569(8) Uani 1 1 d . . . . .
H7 H 0.4076 0.1950 0.5932 0.068 Uiso 1 1 calc R . . . .
C8 C 0.3880(4) 0.31090(16) 0.59292(9) 0.0424(6) Uani 1 1 d . . . . .
C9 C 0.3473(4) 0.33658(15) 0.64332(9) 0.0392(6) Uani 1 1 d . . . . .
C10 C 0.3356(4) 0.29443(14) 0.68742(10) 0.0395(6) Uani 1 1 d . . . . .
H10 H 0.3482 0.2413 0.6866 0.047 Uiso 1 1 calc R . . . .
C11 C 0.3058(4) 0.33047(16) 0.73137(9) 0.0394(6) Uani 1 1 d . . . . .
C12 C 0.2871(4) 0.41352(17) 0.73289(10) 0.0463(7) Uani 1 1 d . . . . .
C13 C 0.2994(4) 0.28503(16) 0.77760(9) 0.0410(6) Uani 1 1 d . . . . .
C14 C 0.3636(4) 0.31373(18) 0.82228(10) 0.0505(7) Uani 1 1 d . . . . .
H14 H 0.4034 0.3643 0.8242 0.061 Uiso 1 1 calc R . . . .
C15 C 0.3686(6) 0.2679(2) 0.86372(12) 0.0648(9) Uani 1 1 d . . . . .
H15 H 0.4118 0.2878 0.8933 0.078 Uiso 1 1 calc R . . . .
C16 C 0.3101(6) 0.1929(2) 0.86162(12) 0.0720(11) Uani 1 1 d . . . . .
H16 H 0.3153 0.1622 0.8896 0.086 Uiso 1 1 calc R . . . .
C17 C 0.2437(5) 0.16344(19) 0.81808(12) 0.0640(9) Uani 1 1 d . . . . .
H17 H 0.2041 0.1128 0.8166 0.077 Uiso 1 1 calc R . . . .
C18 C 0.2363(4) 0.20983(17) 0.77654(11) 0.0509(7) Uani 1 1 d . . . . .
H18 H 0.1883 0.1902 0.7475 0.061 Uiso 1 1 calc R . . . .
C19 C 0.1795(4) 0.48113(19) 0.57238(12) 0.0538(8) Uani 1 1 d . . . . .
C20 C 0.6618(4) 0.4865(2) 0.60206(13) 0.0593(8) Uani 1 1 d . . . . .
H20A H 0.6950 0.4397 0.5856 0.089 Uiso 1 1 calc GR . . . .
H20B H 0.6656 0.4788 0.6371 0.089 Uiso 1 1 calc GR . . . .
H20C H 0.7450 0.5265 0.5931 0.089 Uiso 1 1 calc GR . . . .
C21 C 0.3132(6) 0.53743(17) 0.69179(13) 0.0660(10) Uani 1 1 d . . . . .
H21A H 0.3500 0.5593 0.6609 0.099 Uiso 1 1 calc GR . . . .
H21B H 0.3979 0.5519 0.7170 0.099 Uiso 1 1 calc GR . . . .
H21C H 0.1950 0.5561 0.7003 0.099 Uiso 1 1 calc GR . . . .


_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 C19 1.337(4) . ?
F2 C19 1.324(4) . ?
F3 C19 1.328(4) . ?
O1 C12 1.229(3) . ?
O2 C2 1.410(3) . ?
O2 C20 1.429(4) . ?
N1 C1 1.366(3) . ?
N1 C12 1.416(3) . ?
N1 C21 1.482(4) . ?
C1 C2 1.543(3) . ?
C1 C9 1.348(4) . ?
C2 C3 1.522(4) . ?
C2 C19 1.530(4) . ?
C3 C4 1.384(4) . ?
C3 C8 1.392(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.371(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.388(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.382(4) . ?
C8 C9 1.470(3) . ?
C9 C10 1.407(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.366(4) . ?
C11 C12 1.453(4) . ?
C11 C13 1.484(3) . ?
C13 C14 1.394(4) . ?
C13 C18 1.390(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.379(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.376(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.379(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.388(4) . ?
C18 H18 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

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 O2 C20 113.1(2) . . ?
C1 N1 C12 121.6(2) . . ?
C1 N1 C21 123.8(2) . . ?
C12 N1 C21 114.4(2) . . ?
N1 C1 C2 127.8(2) . . ?
C9 C1 N1 121.4(2) . . ?
C9 C1 C2 110.8(2) . . ?
O2 C2 C1 115.9(2) . . ?
O2 C2 C3 115.2(2) . . ?
O2 C2 C19 104.5(2) . . ?
C3 C2 C1 100.7(2) . . ?
C3 C2 C19 108.5(2) . . ?
C19 C2 C1 112.0(2) . . ?
C4 C3 C2 128.5(3) . . ?
C4 C3 C8 121.1(3) . . ?
C8 C3 C2 110.4(2) . . ?
C3 C4 H4 121.0 . . ?
C3 C4 C5 117.9(3) . . ?
C5 C4 H4 121.0 . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.2(3) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C7 121.1(3) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 H7 120.8 . . ?
C8 C7 C6 118.4(3) . . ?
C8 C7 H7 120.8 . . ?
C3 C8 C9 108.2(2) . . ?
C7 C8 C3 120.3(3) . . ?
C7 C8 C9 131.5(3) . . ?
C1 C9 C8 109.7(2) . . ?
C1 C9 C10 119.9(2) . . ?
C10 C9 C8 130.2(2) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.9(2) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C12 119.8(2) . . ?
C10 C11 C13 119.9(2) . . ?
C12 C11 C13 120.2(2) . . ?
O1 C12 N1 118.4(3) . . ?
O1 C12 C11 125.3(3) . . ?
N1 C12 C11 116.3(2) . . ?
C14 C13 C11 122.2(3) . . ?
C18 C13 C11 119.7(2) . . ?
C18 C13 C14 118.0(3) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.7(3) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.4(3) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.0(3) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 120.2 . . ?
C16 C17 C18 119.6(3) . . ?
C18 C17 H17 120.2 . . ?
C13 C18 H18 119.4 . . ?
C17 C18 C13 121.2(3) . . ?
C17 C18 H18 119.4 . . ?
F1 C19 C2 110.7(2) . . ?
F2 C19 F1 106.6(3) . . ?
F2 C19 F3 106.8(3) . . ?
F2 C19 C2 112.0(2) . . ?
F3 C19 F1 106.3(3) . . ?
F3 C19 C2 114.0(3) . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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
O2 C2 C3 C4 -48.2(4) . . . . ?
O2 C2 C3 C8 130.7(2) . . . . ?
O2 C2 C19 F1 177.6(2) . . . . ?
O2 C2 C19 F2 58.9(3) . . . . ?
O2 C2 C19 F3 -62.5(3) . . . . ?
N1 C1 C2 O2 48.6(4) . . . . ?
N1 C1 C2 C3 173.6(3) . . . . ?
N1 C1 C2 C19 -71.2(4) . . . . ?
N1 C1 C9 C8 -175.8(2) . . . . ?
N1 C1 C9 C10 -0.3(4) . . . . ?
C1 N1 C12 O1 -177.5(3) . . . . ?
C1 N1 C12 C11 3.7(4) . . . . ?
C1 C2 C3 C4 -173.7(3) . . . . ?
C1 C2 C3 C8 5.3(3) . . . . ?
C1 C2 C19 F1 -56.1(3) . . . . ?
C1 C2 C19 F2 -174.9(3) . . . . ?
C1 C2 C19 F3 63.7(3) . . . . ?
C1 C9 C10 C11 1.7(4) . . . . ?
C2 C1 C9 C8 2.7(3) . . . . ?
C2 C1 C9 C10 178.2(2) . . . . ?
C2 C3 C4 C5 178.9(3) . . . . ?
C2 C3 C8 C7 178.9(3) . . . . ?
C2 C3 C8 C9 -4.1(3) . . . . ?
C3 C2 C19 F1 54.2(3) . . . . ?
C3 C2 C19 F2 -64.6(3) . . . . ?
C3 C2 C19 F3 174.0(2) . . . . ?
C3 C4 C5 C6 1.9(5) . . . . ?
C3 C8 C9 C1 0.8(3) . . . . ?
C3 C8 C9 C10 -174.0(3) . . . . ?
C4 C3 C8 C7 -2.0(4) . . . . ?
C4 C3 C8 C9 175.0(3) . . . . ?
C4 C5 C6 C7 -1.9(6) . . . . ?
C5 C6 C7 C8 -0.2(6) . . . . ?
C6 C7 C8 C3 2.1(5) . . . . ?
C6 C7 C8 C9 -174.1(3) . . . . ?
C7 C8 C9 C1 177.4(3) . . . . ?
C7 C8 C9 C10 2.5(5) . . . . ?
C8 C3 C4 C5 0.0(4) . . . . ?
C8 C9 C10 C11 176.2(3) . . . . ?
C9 C1 C2 O2 -129.8(3) . . . . ?
C9 C1 C2 C3 -4.8(3) . . . . ?
C9 C1 C2 C19 110.4(3) . . . . ?
C9 C10 C11 C12 -0.4(4) . . . . ?
C9 C10 C11 C13 -178.2(3) . . . . ?
C10 C11 C12 O1 179.0(3) . . . . ?
C10 C11 C12 N1 -2.2(4) . . . . ?
C10 C11 C13 C14 145.4(3) . . . . ?
C10 C11 C13 C18 -31.2(4) . . . . ?
C11 C13 C14 C15 -174.9(3) . . . . ?
C11 C13 C18 C17 174.1(3) . . . . ?
C12 N1 C1 C2 179.3(3) . . . . ?
C12 N1 C1 C9 -2.5(4) . . . . ?
C12 C11 C13 C14 -32.4(4) . . . . ?
C12 C11 C13 C18 151.0(3) . . . . ?
C13 C11 C12 O1 -3.2(5) . . . . ?
C13 C11 C12 N1 175.6(2) . . . . ?
C13 C14 C15 C16 -0.1(6) . . . . ?
C14 C13 C18 C17 -2.7(5) . . . . ?
C14 C15 C16 C17 -0.8(6) . . . . ?
C15 C16 C17 C18 0.0(6) . . . . ?
C16 C17 C18 C13 1.8(6) . . . . ?
C18 C13 C14 C15 1.8(5) . . . . ?
C19 C2 C3 C4 68.5(4) . . . . ?
C19 C2 C3 C8 -112.5(3) . . . . ?
C20 O2 C2 C1 59.5(3) . . . . ?
C20 O2 C2 C3 -57.7(3) . . . . ?
C20 O2 C2 C19 -176.8(2) . . . . ?
C21 N1 C1 C2 -5.5(5) . . . . ?
C21 N1 C1 C9 172.7(3) . . . . ?
C21 N1 C12 O1 6.9(4) . . . . ?
C21 N1 C12 C11 -172.0(3) . . . . ?

_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 1.919
_oxdiff_exptl_absorpt_empirical_full_min 0.442
####################################################################### 
# 
# 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_3ma
_database_code_depnum_ccdc_archive 'CCDC 2519849'
loop_
_audit_author_name
_audit_author_address
'Xuesen Fan'
;Henan Normal University
China
;
_audit_update_record             
;
2026-01-02 deposited with the CCDC.	2026-01-15 downloaded from the CCDC.
;
_audit_creation_date             2025-12-29
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H10 Cl2 F3 N O2'
_chemical_formula_sum            'C19 H10 Cl2 F3 N O2'
_chemical_formula_weight         412.18
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHONCl
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   6.3061(2)
_cell_length_b                   16.2896(4)
_cell_length_c                   17.1248(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.141(2)
_cell_angle_gamma                90
_cell_volume                     1741.40(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3657
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8320
_cell_measurement_theta_min      5.4190
_shelx_estimated_absorpt_T_max   0.703
_shelx_estimated_absorpt_T_min   0.518
_exptl_absorpt_coefficient_mu    3.783
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
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    1.572
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7031
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.134
_diffrn_reflns_theta_min         3.763
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -71.00 -39.00   1.00    1.10    --  -35.62  94.00  19.00   32
  2  ω      2.00  28.00   1.00    1.10    --   35.62 -94.00 -91.00   26
  3  ω     38.00  86.00   1.00    4.38    --  106.81 -94.00 -91.00   48
  4  ω    109.00 136.00   1.00    4.38    --  106.81  94.00  19.00   27
  5  ω   -100.00 -22.00   1.00    1.10    --  -35.62 -57.00-180.00   78
  6  ω     69.00 108.00   1.00    1.10    --   35.62 178.00-120.00   39
  7  ω     80.00 107.00   1.00    1.10    --   35.62-178.00 -90.00   27
  8  ω     64.00 108.00   1.00    1.10    --   35.62 178.00  30.00   44
  9  ω     20.00 103.00   1.00    1.10    --   35.62  38.00  60.00   83
 10  ω     61.00  88.00   1.00    1.10    --   35.62 178.00 -90.00   27
 11  ω     41.00  89.00   1.00    4.38    --  106.81-111.00   0.00   48
 12  ω     50.00  95.00   1.00    4.38    --  106.81 -94.00   0.00   45
 13  ω    133.00 166.00   1.00    4.38    --  106.81  61.00-180.00   33
 14  ω     40.00 102.00   1.00    4.38    --  106.81-111.00-120.00   62
 15  ω     47.00  84.00   1.00    4.38    --  106.81 -45.00   0.00   37
 16  ω     89.00 116.00   1.00    4.38    --  106.81 -45.00   0.00   27
 17  ω    116.00 172.00   1.00    4.38    --  106.81  77.00   0.00   56
 18  ω    122.00 169.00   1.00    4.38    --  106.81  77.00 -90.00   47
 19  ω     89.00 122.00   1.00    4.38    --  106.81  61.00-180.00   33
 20  ω     52.00 128.00   1.00    4.38    --  106.81 -77.00  60.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1218015000
_diffrn_orient_matrix_UB_12      -0.0709166000
_diffrn_orient_matrix_UB_13      -0.0332895000
_diffrn_orient_matrix_UB_21      0.0217405000
_diffrn_orient_matrix_UB_22      0.0517471000
_diffrn_orient_matrix_UB_23      -0.0737636000
_diffrn_orient_matrix_UB_31      0.2133814000
_diffrn_orient_matrix_UB_32      0.0352122000
_diffrn_orient_matrix_UB_33      0.0414201000
_diffrn_oxdiff_digest_frames     
;
01030527c9d6d888035187627cd8de7d9b000297ff1
;
_diffrn_oxdiff_digest_hkl        
;
0107864f1a9cca47ad50ca70d78610a1412170
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2767
_reflns_number_total             3304
_reflns_odcompleteness_completeness 99.78
_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 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0686
_refine_ls_restrained_S_all      1.115
_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)+(0.1020P)²+1.5194P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2068
_refine_ls_wR_factor_ref         0.2138
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15), C18(H18),
 C19(H19)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 1.24671(19) 0.42349(8) 0.76984(9) 0.0892(5) Uani 1 1 d . . . . .
Cl2 Cl 1.2804(3) 0.50482(14) 0.93758(11) 0.1362(8) Uani 1 1 d . . . . .
F1 F 0.1969(5) 0.67672(19) 0.40777(15) 0.0840(8) Uani 1 1 d . . . . .
F2 F 0.1896(4) 0.78151(17) 0.48262(17) 0.0798(8) Uani 1 1 d . . . . .
F3 F -0.0917(4) 0.7463(2) 0.40521(16) 0.0864(9) Uani 1 1 d . . . . .
O1 O 0.6723(4) 0.51605(17) 0.58024(14) 0.0560(6) Uani 1 1 d . . . . .
O2 O -0.1098(4) 0.59942(17) 0.47757(15) 0.0584(7) Uani 1 1 d . . . . .
H2 H -0.1753 0.5747 0.5083 0.088 Uiso 1 1 calc GR . . . .
N1 N 0.3621(4) 0.58425(17) 0.55363(15) 0.0444(6) Uani 1 1 d . . . . .
H1 H 0.3529 0.5674 0.5057 0.053 Uiso 1 1 calc R . . . .
C1 C 0.5342(5) 0.5595(2) 0.60609(19) 0.0436(7) Uani 1 1 d . . . . .
C2 C 0.5423(5) 0.5875(2) 0.68737(18) 0.0430(7) Uani 1 1 d . . . . .
C3 C 0.3796(5) 0.6368(2) 0.70516(19) 0.0446(7) Uani 1 1 d . . . . .
H3 H 0.3814 0.6545 0.7569 0.054 Uiso 1 1 calc R . . . .
C4 C 0.2109(5) 0.66145(19) 0.64795(19) 0.0421(7) Uani 1 1 d . . . . .
C5 C 0.2062(5) 0.63366(19) 0.57303(19) 0.0423(7) Uani 1 1 d . . . . .
C6 C 0.0767(6) 0.7172(3) 0.4530(2) 0.0625(10) Uani 1 1 d . . . . .
C7 C 0.0111(5) 0.6632(2) 0.5180(2) 0.0487(8) Uani 1 1 d . . . . .
C8 C -0.1003(5) 0.7140(2) 0.5758(2) 0.0489(8) Uani 1 1 d . . . . .
C9 C -0.2903(6) 0.7571(2) 0.5607(3) 0.0611(9) Uani 1 1 d . . . . .
H9 H -0.3699 0.7573 0.5106 0.073 Uiso 1 1 calc R . . . .
C10 C -0.3590(7) 0.8000(3) 0.6226(3) 0.0689(11) Uani 1 1 d . . . . .
H10 H -0.4862 0.8297 0.6138 0.083 Uiso 1 1 calc R . . . .
C11 C -0.2411(7) 0.7994(3) 0.6968(3) 0.0659(11) Uani 1 1 d . . . . .
H11 H -0.2896 0.8289 0.7373 0.079 Uiso 1 1 calc R . . . .
C12 C -0.0508(6) 0.7552(2) 0.7122(2) 0.0562(9) Uani 1 1 d . . . . .
H12 H 0.0274 0.7544 0.7625 0.067 Uiso 1 1 calc R . . . .
C13 C 0.0195(5) 0.7126(2) 0.6507(2) 0.0465(7) Uani 1 1 d . . . . .
C14 C 0.7252(6) 0.5641(2) 0.7478(2) 0.0481(7) Uani 1 1 d . . . . .
C15 C 0.8852(6) 0.5107(2) 0.7337(2) 0.0530(8) Uani 1 1 d . . . . .
H15 H 0.8795 0.4865 0.6843 0.064 Uiso 1 1 calc R . . . .
C16 C 1.0543(6) 0.4925(2) 0.7919(3) 0.0602(9) Uani 1 1 d . . . . .
C17 C 1.0693(8) 0.5267(3) 0.8639(3) 0.0801(13) Uani 1 1 d . . . . .
C18 C 0.9146(10) 0.5801(4) 0.8795(3) 0.107(2) Uani 1 1 d . . . . .
H18 H 0.9246 0.6046 0.9289 0.128 Uiso 1 1 calc R . . . .
C19 C 0.7442(9) 0.5980(4) 0.8231(3) 0.0857(16) Uani 1 1 d . . . . .
H19 H 0.6388 0.6338 0.8355 0.103 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 C16 1.734(4) . ?
Cl2 C17 1.736(4) . ?
F1 C6 1.332(5) . ?
F2 C6 1.327(5) . ?
F3 C6 1.333(5) . ?
O1 C1 1.250(4) . ?
O2 H2 0.8200 . ?
O2 C7 1.410(4) . ?
N1 H1 0.8600 . ?
N1 C1 1.368(4) . ?
N1 C5 1.348(4) . ?
C1 C2 1.459(4) . ?
C2 C3 1.371(5) . ?
C2 C14 1.486(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.399(5) . ?
C4 C5 1.357(4) . ?
C4 C13 1.473(4) . ?
C5 C7 1.519(4) . ?
C6 C7 1.521(5) . ?
C7 C8 1.536(5) . ?
C8 C9 1.380(5) . ?
C8 C13 1.395(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.389(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.379(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.392(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.385(5) . ?
C14 C15 1.379(5) . ?
C14 C19 1.393(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.384(6) . ?
C16 C17 1.344(7) . ?
C17 C18 1.362(8) . ?
C18 H18 0.9300 . ?
C18 C19 1.370(7) . ?
C19 H19 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
C7 O2 H2 109.5 . . ?
C1 N1 H1 118.2 . . ?
C5 N1 H1 118.2 . . ?
C5 N1 C1 123.5(3) . . ?
O1 C1 N1 117.5(3) . . ?
O1 C1 C2 125.6(3) . . ?
N1 C1 C2 116.8(3) . . ?
C1 C2 C14 120.2(3) . . ?
C3 C2 C1 118.0(3) . . ?
C3 C2 C14 121.8(3) . . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 122.1(3) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 C13 133.2(3) . . ?
C5 C4 C3 118.6(3) . . ?
C5 C4 C13 108.1(3) . . ?
N1 C5 C4 120.9(3) . . ?
N1 C5 C7 126.2(3) . . ?
C4 C5 C7 112.9(3) . . ?
F1 C6 F3 106.8(3) . . ?
F1 C6 C7 112.1(3) . . ?
F2 C6 F1 107.1(3) . . ?
F2 C6 F3 106.9(4) . . ?
F2 C6 C7 111.3(3) . . ?
F3 C6 C7 112.3(3) . . ?
O2 C7 C5 113.9(3) . . ?
O2 C7 C6 104.5(3) . . ?
O2 C7 C8 116.7(3) . . ?
C5 C7 C6 110.9(3) . . ?
C5 C7 C8 100.1(3) . . ?
C6 C7 C8 110.9(3) . . ?
C9 C8 C7 128.1(3) . . ?
C9 C8 C13 121.6(3) . . ?
C13 C8 C7 110.3(3) . . ?
C8 C9 H9 121.0 . . ?
C8 C9 C10 117.9(4) . . ?
C10 C9 H9 121.0 . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 120.9(4) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 121.1(4) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 120.8 . . ?
C13 C12 C11 118.4(4) . . ?
C13 C12 H12 120.8 . . ?
C8 C13 C4 108.6(3) . . ?
C12 C13 C4 131.3(3) . . ?
C12 C13 C8 120.1(3) . . ?
C15 C14 C2 123.8(3) . . ?
C15 C14 C19 116.3(4) . . ?
C19 C14 C2 120.0(3) . . ?
C14 C15 H15 119.4 . . ?
C14 C15 C16 121.2(4) . . ?
C16 C15 H15 119.4 . . ?
C15 C16 Cl1 118.3(3) . . ?
C17 C16 Cl1 120.5(3) . . ?
C17 C16 C15 121.2(4) . . ?
C16 C17 Cl2 121.9(4) . . ?
C16 C17 C18 119.0(4) . . ?
C18 C17 Cl2 119.0(4) . . ?
C17 C18 H18 119.6 . . ?
C17 C18 C19 120.7(5) . . ?
C19 C18 H18 119.6 . . ?
C14 C19 H19 119.2 . . ?
C18 C19 C14 121.6(4) . . ?
C18 C19 H19 119.2 . . ?

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
Cl1 C16 C17 Cl2 0.6(6) . . . . ?
Cl1 C16 C17 C18 -179.4(5) . . . . ?
Cl2 C17 C18 C19 -179.2(6) . . . . ?
F1 C6 C7 O2 -61.3(4) . . . . ?
F1 C6 C7 C5 61.9(4) . . . . ?
F1 C6 C7 C8 172.2(3) . . . . ?
F2 C6 C7 O2 178.8(3) . . . . ?
F2 C6 C7 C5 -58.0(4) . . . . ?
F2 C6 C7 C8 52.3(4) . . . . ?
F3 C6 C7 O2 58.9(4) . . . . ?
F3 C6 C7 C5 -177.9(3) . . . . ?
F3 C6 C7 C8 -67.6(4) . . . . ?
O1 C1 C2 C3 178.2(3) . . . . ?
O1 C1 C2 C14 -0.6(5) . . . . ?
O2 C7 C8 C9 -56.4(5) . . . . ?
O2 C7 C8 C13 124.0(3) . . . . ?
N1 C1 C2 C3 -0.6(4) . . . . ?
N1 C1 C2 C14 -179.3(3) . . . . ?
N1 C5 C7 O2 53.6(4) . . . . ?
N1 C5 C7 C6 -64.1(4) . . . . ?
N1 C5 C7 C8 178.8(3) . . . . ?
C1 N1 C5 C4 -0.7(5) . . . . ?
C1 N1 C5 C7 -179.8(3) . . . . ?
C1 C2 C3 C4 -1.0(5) . . . . ?
C1 C2 C14 C15 -5.4(5) . . . . ?
C1 C2 C14 C19 173.1(4) . . . . ?
C2 C3 C4 C5 1.8(5) . . . . ?
C2 C3 C4 C13 179.7(3) . . . . ?
C2 C14 C15 C16 178.6(3) . . . . ?
C2 C14 C19 C18 -177.7(6) . . . . ?
C3 C2 C14 C15 175.9(3) . . . . ?
C3 C2 C14 C19 -5.6(6) . . . . ?
C3 C4 C5 N1 -0.9(5) . . . . ?
C3 C4 C5 C7 178.3(3) . . . . ?
C3 C4 C13 C8 -177.6(3) . . . . ?
C3 C4 C13 C12 2.3(6) . . . . ?
C4 C5 C7 O2 -125.5(3) . . . . ?
C4 C5 C7 C6 116.8(3) . . . . ?
C4 C5 C7 C8 -0.3(4) . . . . ?
C5 N1 C1 O1 -177.4(3) . . . . ?
C5 N1 C1 C2 1.5(5) . . . . ?
C5 C4 C13 C8 0.5(4) . . . . ?
C5 C4 C13 C12 -179.7(4) . . . . ?
C5 C7 C8 C9 -179.7(4) . . . . ?
C5 C7 C8 C13 0.6(4) . . . . ?
C6 C7 C8 C9 63.1(5) . . . . ?
C6 C7 C8 C13 -116.6(3) . . . . ?
C7 C8 C9 C10 -179.1(4) . . . . ?
C7 C8 C13 C4 -0.7(4) . . . . ?
C7 C8 C13 C12 179.5(3) . . . . ?
C8 C9 C10 C11 -0.2(6) . . . . ?
C9 C8 C13 C4 179.6(3) . . . . ?
C9 C8 C13 C12 -0.2(5) . . . . ?
C9 C10 C11 C12 -0.4(7) . . . . ?
C10 C11 C12 C13 0.8(6) . . . . ?
C11 C12 C13 C4 179.8(4) . . . . ?
C11 C12 C13 C8 -0.5(5) . . . . ?
C13 C4 C5 N1 -179.3(3) . . . . ?
C13 C4 C5 C7 -0.1(4) . . . . ?
C13 C8 C9 C10 0.6(6) . . . . ?
C14 C2 C3 C4 177.7(3) . . . . ?
C14 C15 C16 Cl1 179.0(3) . . . . ?
C14 C15 C16 C17 -0.6(6) . . . . ?
C15 C14 C19 C18 0.9(8) . . . . ?
C15 C16 C17 Cl2 -179.8(3) . . . . ?
C15 C16 C17 C18 0.1(8) . . . . ?
C16 C17 C18 C19 0.8(11) . . . . ?
C17 C18 C19 C14 -1.4(11) . . . . ?
C19 C14 C15 C16 0.0(6) . . . . ?

_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 1.913
_oxdiff_exptl_absorpt_empirical_full_min 0.503
