# Supplementary Information (SI) for Chemical Science.
# 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_s6736r
_database_code_depnum_ccdc_archive 'CCDC 2475750'
loop_
_audit_author_name
_audit_author_address
'Avantika Hasija'
;University of Manchester
United Kingdom
;
_audit_update_record             
;
2025-07-24 deposited with the CCDC.	2026-06-08 downloaded from the CCDC.
;
_audit_creation_date             2025-07-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7308)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H7 Br F3 N O'
_chemical_formula_sum            'C13 H7 Br F3 N O'
_chemical_formula_weight         330.11
_chemical_melting_point          ?
_chemical_oxdiff_formula         C13H7BrF3NO
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'
Br Br -0.6763 1.2805 '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/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                   9.7276(3)
_cell_length_b                   7.63087(19)
_cell_length_c                   16.6784(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.133(3)
_cell_angle_gamma                90
_cell_volume                     1195.10(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3864
_cell_measurement_temperature    99.97(10)
_cell_measurement_theta_max      74.7560
_cell_measurement_theta_min      4.7020
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.002
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.571
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.112a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.835
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-6 0 -1 0.0175
6 0 1 0.0085
1 5 -3 0.0787
2 0 -11 0.0307
-2 0 11 0.0307
-1 -4 5 0.0891
3 0 7 0.0178

_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.061
_exptl_crystal_size_min          0.026
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-5.9952 -0.0631 -0.5857 -0.1836 0.9812 0.0593
5.9952 0.0631 0.5857 0.1836 -0.9812 -0.0593
0.9209 4.7317 -3.1040 -0.0033 -0.0137 -0.9999
2.0944 0.2395 -10.7808 -0.9266 -0.1755 -0.3326
-2.0944 -0.2395 10.7808 0.9266 0.1755 0.3326
-1.1370 -4.4821 4.5385 0.1434 0.0322 0.9891
3.0000 0.0000 7.0000 0.7023 -0.5912 0.1412

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6849
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.071
_diffrn_reflns_theta_min         4.709
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00 -41.00   0.50    0.05    --  -46.62 -22.00 -63.00  158
  2  ω   -172.00-102.00   0.50    0.07    -- -109.00 -15.00   0.00  140
  3  ω   -126.00-101.00   0.50    0.07    -- -109.00 -22.00 -63.00   50
  4  ω    -26.00  11.00   0.50    0.05    --  -46.62  38.00-120.00   74
  5  ω    -79.00 -54.00   0.50    0.07    -- -109.00 125.00-150.00   50
  6  ω   -112.00 -86.00   0.50    0.07    -- -109.00 125.00-150.00   52
  7  ω    -64.00 -39.00   0.50    0.07    -- -109.00  61.00 -30.00   50
  8  ω    -22.00   3.00   0.50    0.05    --  -46.62  22.00 102.00   50
  9  ω     46.00  71.00   0.50    0.05    --   46.62  22.00 102.00   50
 10  ω     72.00 120.00   0.50    0.05    --   46.62  22.00 102.00   96
 11  ω     91.00 175.00   0.50    0.07    --  107.75  61.00  30.00  168
 12  ω    101.00 169.00   0.50    0.07    --  107.75  22.00 102.00  136
 13  ω     59.00 108.00   0.50    0.07    --  107.75 -77.00 120.00   98
 14  ω     36.00  69.00   0.50    0.07    --  107.75 -61.00  90.00   66
 15  ω     39.00  69.00   0.50    0.07    --  107.75 -61.00  30.00   60
 16  ω     44.00  70.00   0.50    0.07    --  107.75 -61.00 150.00   52
 17  ω     44.00  70.00   0.50    0.07    --  107.75 -61.00 -30.00   52
 18  ω     46.00  71.00   0.50    0.07    --  107.75 -61.00 -60.00   50
 19  ω     36.00  70.00   0.50    0.07    --  107.75 -61.00 -90.00   68
 20  ω     46.00  72.00   0.50    0.07    --  107.75 -61.00-150.00   52
 21  ω     36.00  72.00   0.50    0.07    --  107.75 -61.00-180.00   72
 22  ω     -4.00  43.00   0.50    0.05    --   46.62 -38.00-180.00   94
 23  ω    -25.00   0.00   0.50    0.05    --   46.62 -22.00 -63.00   50
 24  ω    -28.00  20.00   0.50    0.05    --   46.62 -19.00 150.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0211265000
_diffrn_orient_matrix_UB_12      0.0550671000
_diffrn_orient_matrix_UB_13      0.0912763000
_diffrn_orient_matrix_UB_21      -0.1624163000
_diffrn_orient_matrix_UB_22      0.0189731000
_diffrn_orient_matrix_UB_23      -0.0148528000
_diffrn_orient_matrix_UB_31      -0.0102558000
_diffrn_orient_matrix_UB_32      -0.1932093000
_diffrn_orient_matrix_UB_33      0.0245666000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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                2057
_reflns_number_total             2423
_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 1.171.43.112a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 44.117a 64-bit (release 07-07-2025))'
_computing_data_reduction        'CrysAlisPro 1.171.43.112a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.891
_refine_diff_density_min         -1.265
_refine_diff_density_rms         0.112
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2423
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0430
_refine_ls_restrained_S_all      1.081
_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)+(0.0651P)²+0.9228P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1153
_refine_ls_wR_factor_ref         0.1198
_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:
 C9(H9), C3(H3), C13(H13), C10(H10), C1(H1), C12(H12), C11(H11)
;
_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
Br1 Br 0.78135(4) 0.55409(5) 0.56213(2) 0.02834(17) Uani 1 1 d . . . . .
F2 F 0.2218(2) 0.9208(3) 0.67344(13) 0.0316(5) Uani 1 1 d . . . . .
F1 F 0.2192(3) 1.0491(3) 0.55847(14) 0.0363(6) Uani 1 1 d . . . . .
F3 F 0.1192(2) 0.7984(3) 0.55688(14) 0.0380(5) Uani 1 1 d . . . . .
O1 O 0.4963(3) 0.7350(4) 0.80540(15) 0.0340(6) Uani 1 1 d . . . . .
N1 N 0.4077(3) 0.8299(4) 0.52387(16) 0.0240(6) Uani 1 1 d . . . . .
C2 C 0.6130(4) 0.6552(5) 0.5781(2) 0.0230(7) Uani 1 1 d . . . . .
C9 C 0.2207(4) 0.4603(4) 0.6805(2) 0.0251(7) Uani 1 1 d . . . . .
H9 H 0.249649 0.460788 0.630344 0.030 Uiso 1 1 calc R U . . .
C8 C 0.2912(4) 0.5654(4) 0.7467(2) 0.0230(7) Uani 1 1 d . . . . .
C3 C 0.5771(4) 0.6317(4) 0.6520(2) 0.0238(7) Uani 1 1 d . . . . .
H3 H 0.637783 0.567603 0.696187 0.029 Uiso 1 1 calc R U . . .
C4 C 0.4508(4) 0.7035(4) 0.66071(19) 0.0225(7) Uani 1 1 d . . . . .
C13 C 0.2484(4) 0.5638(5) 0.8214(2) 0.0246(7) Uani 1 1 d . . . . .
H13 H 0.296674 0.634202 0.867113 0.029 Uiso 1 1 calc R U . . .
C10 C 0.1085(4) 0.3552(5) 0.6875(2) 0.0271(7) Uani 1 1 d . . . . .
H10 H 0.060813 0.283414 0.642206 0.033 Uiso 1 1 calc R U . . .
C1 C 0.5262(4) 0.7542(5) 0.5151(2) 0.0267(7) Uani 1 1 d . . . . .
H1 H 0.552093 0.768313 0.464337 0.032 Uiso 1 1 calc R U . . .
C7 C 0.4151(4) 0.6734(5) 0.7434(2) 0.0244(7) Uani 1 1 d . . . . .
C6 C 0.2331(4) 0.8933(5) 0.5955(2) 0.0267(7) Uani 1 1 d . . . . .
C5 C 0.3708(4) 0.8039(4) 0.5949(2) 0.0231(7) Uani 1 1 d . . . . .
C12 C 0.1358(4) 0.4590(5) 0.8274(2) 0.0283(8) Uani 1 1 d . . . . .
H12 H 0.106017 0.458109 0.877348 0.034 Uiso 1 1 calc R U . . .
C11 C 0.0656(4) 0.3546(5) 0.7608(2) 0.0279(8) Uani 1 1 d . . . . .
H11 H -0.011749 0.282784 0.765424 0.033 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
Br1 C2 1.891(3) . ?
F2 C6 1.350(4) . ?
F1 C6 1.330(4) . ?
F3 C6 1.339(4) . ?
O1 C7 1.220(4) . ?
N1 C1 1.332(5) . ?
N1 C5 1.340(4) . ?
C2 C3 1.378(5) . ?
C2 C1 1.387(5) . ?
C9 H9 0.9500 . ?
C9 C8 1.391(5) . ?
C9 C10 1.383(5) . ?
C8 C13 1.414(4) . ?
C8 C7 1.473(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.388(5) . ?
C4 C7 1.524(4) . ?
C4 C5 1.396(5) . ?
C13 H13 0.9500 . ?
C13 C12 1.381(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.392(5) . ?
C1 H1 0.9500 . ?
C6 C5 1.505(5) . ?
C12 H12 0.9500 . ?
C12 C11 1.393(5) . ?
C11 H11 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
C1 N1 C5 118.2(3) . . ?
C3 C2 Br1 120.2(3) . . ?
C3 C2 C1 120.2(3) . . ?
C1 C2 Br1 119.6(3) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C10 C9 C8 120.3(3) . . ?
C9 C8 C13 119.8(3) . . ?
C9 C8 C7 122.1(3) . . ?
C13 C8 C7 118.0(3) . . ?
C2 C3 H3 120.7 . . ?
C2 C3 C4 118.7(3) . . ?
C4 C3 H3 120.7 . . ?
C3 C4 C7 116.9(3) . . ?
C3 C4 C5 117.5(3) . . ?
C5 C4 C7 125.6(3) . . ?
C8 C13 H13 120.3 . . ?
C12 C13 C8 119.4(3) . . ?
C12 C13 H13 120.3 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
N1 C1 C2 121.7(3) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
O1 C7 C8 122.6(3) . . ?
O1 C7 C4 117.4(3) . . ?
C8 C7 C4 120.0(3) . . ?
F2 C6 C5 111.9(3) . . ?
F1 C6 F2 106.5(3) . . ?
F1 C6 F3 106.8(3) . . ?
F1 C6 C5 112.7(3) . . ?
F3 C6 F2 106.3(3) . . ?
F3 C6 C5 112.2(3) . . ?
N1 C5 C4 123.6(3) . . ?
N1 C5 C6 112.5(3) . . ?
C4 C5 C6 123.9(3) . . ?
C13 C12 H12 119.8 . . ?
C13 C12 C11 120.4(3) . . ?
C11 C12 H12 119.8 . . ?
C10 C11 C12 120.1(3) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?

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
Br1 C2 C3 C4 -178.2(3) . . . . ?
Br1 C2 C1 N1 -179.1(3) . . . . ?
F2 C6 C5 N1 -158.0(3) . . . . ?
F2 C6 C5 C4 22.6(5) . . . . ?
F1 C6 C5 N1 -37.9(4) . . . . ?
F1 C6 C5 C4 142.6(3) . . . . ?
F3 C6 C5 N1 82.6(4) . . . . ?
F3 C6 C5 C4 -96.8(4) . . . . ?
C2 C3 C4 C7 179.7(3) . . . . ?
C2 C3 C4 C5 -3.4(5) . . . . ?
C9 C8 C13 C12 -0.7(5) . . . . ?
C9 C8 C7 O1 -163.5(4) . . . . ?
C9 C8 C7 C4 13.1(5) . . . . ?
C9 C10 C11 C12 -0.3(5) . . . . ?
C8 C9 C10 C11 0.2(5) . . . . ?
C8 C13 C12 C11 0.5(5) . . . . ?
C3 C2 C1 N1 0.5(5) . . . . ?
C3 C4 C7 O1 62.8(4) . . . . ?
C3 C4 C7 C8 -113.9(4) . . . . ?
C3 C4 C5 N1 1.9(5) . . . . ?
C3 C4 C5 C6 -178.7(3) . . . . ?
C13 C8 C7 O1 13.4(5) . . . . ?
C13 C8 C7 C4 -170.0(3) . . . . ?
C13 C12 C11 C10 0.0(5) . . . . ?
C10 C9 C8 C13 0.3(5) . . . . ?
C10 C9 C8 C7 177.2(3) . . . . ?
C1 N1 C5 C4 0.8(5) . . . . ?
C1 N1 C5 C6 -178.6(3) . . . . ?
C1 C2 C3 C4 2.3(5) . . . . ?
C7 C8 C13 C12 -177.7(3) . . . . ?
C7 C4 C5 N1 178.5(3) . . . . ?
C7 C4 C5 C6 -2.1(5) . . . . ?
C5 N1 C1 C2 -2.0(5) . . . . ?
C5 C4 C7 O1 -113.8(4) . . . . ?
C5 C4 C7 C8 69.4(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 1.619
_oxdiff_exptl_absorpt_empirical_full_min 0.748
####################################################################### 
# 
# 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_s6739r
_database_code_depnum_ccdc_archive 'CCDC 2478546'
loop_
_audit_author_name
_audit_author_address
'Avantika Hasija'
;University of Manchester
United Kingdom
;
_audit_update_record             
;
2025-08-05 deposited with the CCDC.	2026-06-08 downloaded from the CCDC.
;
_audit_creation_date             2025-08-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7308)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H10 F3 N O2'
_chemical_formula_sum            'C19 H10 F3 N O2'
_chemical_formula_weight         341.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         C19H10F3NO2
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      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                   6.3172(3)
_cell_length_b                   9.4347(4)
_cell_length_c                   13.0054(5)
_cell_angle_alpha                104.381(3)
_cell_angle_beta                 101.852(4)
_cell_angle_gamma                95.556(4)
_cell_volume                     725.85(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3641
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      77.1840
_cell_measurement_theta_min      3.6200
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.099
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.878
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.112a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             348
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 1 4 0.0097
4 -1 -4 0.0254
-1 6 -4 0.0410
1 -6 3 0.0521
-2 1 -6 0.0385
2 -2 6 0.0184

_exptl_crystal_size_max          0.138
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.037
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-3.8900 0.9002 3.9924 0.4761 -0.8737 0.0996
3.9011 -0.7739 -4.0030 -0.4772 0.8754 -0.0779
-1.1595 5.6502 -4.2027 -0.4884 -0.4245 0.7624
0.6397 -6.0946 2.5883 0.2958 0.2605 -0.9191
-1.9696 1.4018 -6.3968 -0.7571 -0.6487 -0.0770
1.9693 -1.5236 6.4069 0.7581 0.6497 0.0565

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7026
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.783
_diffrn_reflns_theta_min         3.612
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      3.00  63.00   0.50    0.10    --   46.62-104.00 140.00  120
  2  ω     37.00  73.00   0.50    0.30    --  107.75-125.00 120.00   72
  3  ω     84.00 112.00   0.50    0.30    --  107.75-125.00 120.00   56
  4  ω     82.00 107.00   0.50    0.30    --  107.75-104.00 140.00   50
  5  ω     36.00 109.00   0.50    0.30    --  107.75-125.00   0.00  146
  6  ω     70.00 104.00   0.50    0.30    --  107.75 -95.00 -30.00   68
  7  ω     40.00  66.00   0.50    0.30    --  107.75 -95.00-120.00   52
  8  ω     68.00 105.00   0.50    0.30    --  107.75 -95.00-120.00   74
  9  ω     36.00 105.00   0.50    0.30    --  107.75 -95.00-180.00  138
 10  ω     42.00  68.00   0.50    0.30    --  107.75 -61.00 -90.00   52
 11  ω    -26.00  35.00   0.50    0.10    --   46.62 -38.00   0.00  122
 12  ω    -16.00  23.00   0.50    0.10    --   46.62 -19.00  60.00   78
 13  ω     36.00  68.00   0.50    0.30    --  107.75 -61.00 150.00   64
 14  ω    100.00 125.00   0.50    0.30    --  107.75 104.00-118.00   50
 15  ω    100.00 167.00   0.50    0.30    --  107.75  45.00-150.00  134
 16  ω     98.00 175.00   0.50    0.30    --  107.75  15.00-180.00  154
 17  ω    128.00 155.00   0.50    0.30    --  107.75 104.00-118.00   54
 18  ω   -106.00 -80.00   0.50    0.30    -- -109.00 104.00-118.00   52
 19  ω    -79.00 -39.00   0.50    0.30    -- -109.00 125.00-120.00   80
 20  ω    -90.00 -64.00   0.50    0.10    --  -46.62 125.00 -60.00   52
 21  ω    -50.00 -23.00   0.50    0.10    --  -46.62 125.00 -90.00   54
 22  ω    -79.00  -5.00   0.50    0.10    --  -46.62 104.00-118.00  148
 23  ω    -93.00 -64.00   0.50    0.30    -- -109.00 125.00   0.00   58
 24  ω    -65.00 -40.00   0.50    0.30    -- -109.00  61.00   0.00   50
 25  ω    -63.00 -38.00   0.50    0.30    -- -109.00  61.00  30.00   50
 26  ω    -70.00 -38.00   0.50    0.30    -- -109.00  61.00  60.00   64
 27  ω    -71.00 -42.00   0.50    0.30    -- -109.00  61.00  90.00   58
 28  ω   -107.00 -55.00   0.50    0.30    -- -109.00  77.00 150.00  104
 29  ω    -71.00 -40.00   0.50    0.30    -- -109.00  61.00 -90.00   62
 30  ω   -136.00 -95.00   0.50    0.30    -- -109.00 -15.00-150.00   82
 31  ω   -146.00-121.00   0.50    0.30    -- -109.00 -30.00-180.00   50
 32  ω   -169.00-144.00   0.50    0.30    -- -109.00 -15.00-150.00   50
 33  ω   -174.00 -96.00   0.50    0.30    -- -109.00 -30.00 -30.00  156
 34  ω    -86.00 -40.00   0.50    0.10    --  -46.62 -38.00  30.00   92
 35  ω   -116.00 -24.00   0.50    0.10    --  -46.62 -77.00 150.00  184
 36  ω   -145.00 -92.00   0.50    0.30    -- -109.00-104.00 140.00  106
 37  ω   -173.00-109.00   0.50    0.30    -- -109.00 -95.00   0.00  128
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0000415000
_diffrn_orient_matrix_UB_12      0.0019154000
_diffrn_orient_matrix_UB_13      0.1187889000
_diffrn_orient_matrix_UB_21      0.2474484000
_diffrn_orient_matrix_UB_22      -0.0066735000
_diffrn_orient_matrix_UB_23      0.0237650000
_diffrn_orient_matrix_UB_31      0.0490557000
_diffrn_orient_matrix_UB_32      0.1705155000
_diffrn_orient_matrix_UB_33      0.0342978000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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                2422
_reflns_number_total             2906
_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 1.171.43.112a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 44.117a 64-bit (release 07-07-2025))'
_computing_data_reduction        'CrysAlisPro 1.171.43.112a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2906
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0405
_refine_ls_restrained_S_all      1.048
_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)+(0.0502P)²+0.2211P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1091
_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:
 C9(H9), C3(H3), C2(H2), C16(H16), C17(H17), C1(H1), C18(H18), C12(H12),
 C13(H13), C15(H15)
;
_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
F1 F 0.14351(19) 0.50910(11) 0.91294(9) 0.0341(3) Uani 1 1 d . . . . .
F3 F 0.09346(18) 0.71669(11) 1.01276(9) 0.0336(3) Uani 1 1 d . . . . .
F2 F 0.35380(19) 0.60588(12) 1.07282(9) 0.0366(3) Uani 1 1 d . . . . .
O2 O -0.16052(18) 0.18443(12) 0.42617(9) 0.0220(3) Uani 1 1 d . . . . .
O1 O -0.0112(2) 0.65570(13) 0.74464(10) 0.0293(3) Uani 1 1 d . . . . .
N1 N 0.5640(2) 0.81380(15) 1.01096(11) 0.0245(3) Uani 1 1 d . . . . .
C5 C 0.3998(3) 0.72143(16) 0.93564(13) 0.0210(3) Uani 1 1 d . . . . .
C10 C 0.0115(3) 0.27502(17) 0.50668(12) 0.0200(3) Uani 1 1 d . . . . .
C4 C 0.3677(3) 0.70283(16) 0.82323(12) 0.0207(3) Uani 1 1 d . . . . .
C11 C 0.2106(3) 0.22270(16) 0.50286(12) 0.0198(3) Uani 1 1 d . . . . .
C19 C 0.1580(3) 0.08808(16) 0.41391(12) 0.0200(3) Uani 1 1 d . . . . .
C14 C -0.0670(3) 0.07098(17) 0.37070(12) 0.0209(3) Uani 1 1 d . . . . .
C7 C 0.1641(3) 0.61342(17) 0.74150(13) 0.0214(3) Uani 1 1 d . . . . .
C9 C -0.0079(3) 0.40201(17) 0.58185(12) 0.0206(3) Uani 1 1 d . . . . .
H9 H -0.144748 0.435707 0.582098 0.025 Uiso 1 1 calc R U . . .
C3 C 0.5260(3) 0.78101(17) 0.78897(13) 0.0228(3) Uani 1 1 d . . . . .
H3 H 0.515657 0.768690 0.713269 0.027 Uiso 1 1 calc R U . . .
C8 C 0.1849(3) 0.47873(17) 0.65786(13) 0.0211(3) Uani 1 1 d . . . . .
C6 C 0.2473(3) 0.63755(18) 0.98334(13) 0.0247(3) Uani 1 1 d . . . . .
C2 C 0.6980(3) 0.87664(17) 0.86607(14) 0.0252(3) Uani 1 1 d . . . . .
H2 H 0.807188 0.931058 0.844358 0.030 Uiso 1 1 calc R U . . .
C16 C -0.0591(3) -0.14976(17) 0.23939(13) 0.0228(3) Uani 1 1 d . . . . .
H16 H -0.130630 -0.232107 0.179412 0.027 Uiso 1 1 calc R U . . .
C17 C 0.1667(3) -0.13684(17) 0.28188(13) 0.0235(3) Uani 1 1 d . . . . .
H17 H 0.244859 -0.210655 0.250587 0.028 Uiso 1 1 calc R U . . .
C1 C 0.7075(3) 0.89128(18) 0.97568(14) 0.0260(4) Uani 1 1 d . . . . .
H1 H 0.822305 0.960179 1.028458 0.031 Uiso 1 1 calc R U . . .
C18 C 0.2779(3) -0.01786(17) 0.36896(13) 0.0226(3) Uani 1 1 d . . . . .
H18 H 0.431184 -0.008672 0.397247 0.027 Uiso 1 1 calc R U . . .
C12 C 0.4014(3) 0.30126(17) 0.57800(13) 0.0219(3) Uani 1 1 d . . . . .
H12 H 0.538519 0.268555 0.576074 0.026 Uiso 1 1 calc R U . . .
C13 C 0.3868(3) 0.42846(17) 0.65582(13) 0.0217(3) Uani 1 1 d . . . . .
H13 H 0.515105 0.482277 0.708418 0.026 Uiso 1 1 calc R U . . .
C15 C -0.1810(3) -0.04554(17) 0.28255(13) 0.0231(3) Uani 1 1 d . . . . .
H15 H -0.333804 -0.053543 0.253387 0.028 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 C6 1.336(2) . ?
F3 C6 1.342(2) . ?
F2 C6 1.337(2) . ?
O2 C10 1.3841(19) . ?
O2 C14 1.3890(19) . ?
O1 C7 1.218(2) . ?
N1 C5 1.333(2) . ?
N1 C1 1.333(2) . ?
C5 C4 1.398(2) . ?
C5 C6 1.510(2) . ?
C10 C11 1.401(2) . ?
C10 C9 1.379(2) . ?
C4 C7 1.510(2) . ?
C4 C3 1.395(2) . ?
C11 C19 1.447(2) . ?
C11 C12 1.393(2) . ?
C19 C14 1.394(2) . ?
C19 C18 1.397(2) . ?
C14 C15 1.387(2) . ?
C7 C8 1.490(2) . ?
C9 H9 0.9500 . ?
C9 C8 1.401(2) . ?
C3 H3 0.9500 . ?
C3 C2 1.383(2) . ?
C8 C13 1.406(2) . ?
C2 H2 0.9500 . ?
C2 C1 1.386(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.402(2) . ?
C16 C15 1.387(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.387(2) . ?
C1 H1 0.9500 . ?
C18 H18 0.9500 . ?
C12 H12 0.9500 . ?
C12 C13 1.389(2) . ?
C13 H13 0.9500 . ?
C15 H15 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
C10 O2 C14 105.04(12) . . ?
C1 N1 C5 117.29(14) . . ?
N1 C5 C4 124.25(15) . . ?
N1 C5 C6 113.42(14) . . ?
C4 C5 C6 122.33(15) . . ?
O2 C10 C11 111.81(13) . . ?
C9 C10 O2 124.75(14) . . ?
C9 C10 C11 123.44(15) . . ?
C5 C4 C7 122.73(14) . . ?
C3 C4 C5 116.87(14) . . ?
C3 C4 C7 120.20(14) . . ?
C10 C11 C19 105.53(13) . . ?
C12 C11 C10 119.40(14) . . ?
C12 C11 C19 135.07(15) . . ?
C14 C19 C11 105.78(14) . . ?
C14 C19 C18 119.47(14) . . ?
C18 C19 C11 134.75(15) . . ?
O2 C14 C19 111.84(13) . . ?
C15 C14 O2 124.71(15) . . ?
C15 C14 C19 123.45(15) . . ?
O1 C7 C4 118.84(14) . . ?
O1 C7 C8 122.16(15) . . ?
C8 C7 C4 118.98(14) . . ?
C10 C9 H9 121.7 . . ?
C10 C9 C8 116.51(15) . . ?
C8 C9 H9 121.7 . . ?
C4 C3 H3 120.3 . . ?
C2 C3 C4 119.50(15) . . ?
C2 C3 H3 120.3 . . ?
C9 C8 C7 116.81(15) . . ?
C9 C8 C13 121.15(15) . . ?
C13 C8 C7 122.03(14) . . ?
F1 C6 F3 107.23(14) . . ?
F1 C6 F2 106.90(13) . . ?
F1 C6 C5 112.39(13) . . ?
F3 C6 C5 111.35(13) . . ?
F2 C6 F3 106.74(13) . . ?
F2 C6 C5 111.91(14) . . ?
C3 C2 H2 120.8 . . ?
C3 C2 C1 118.50(15) . . ?
C1 C2 H2 120.8 . . ?
C17 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C15 C16 C17 121.79(15) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 120.98(15) . . ?
C18 C17 H17 119.5 . . ?
N1 C1 C2 123.46(15) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C19 C18 H18 120.9 . . ?
C17 C18 C19 118.14(15) . . ?
C17 C18 H18 120.9 . . ?
C11 C12 H12 120.7 . . ?
C13 C12 C11 118.53(15) . . ?
C13 C12 H12 120.7 . . ?
C8 C13 H13 119.5 . . ?
C12 C13 C8 120.95(15) . . ?
C12 C13 H13 119.5 . . ?
C14 C15 C16 116.15(15) . . ?
C14 C15 H15 121.9 . . ?
C16 C15 H15 121.9 . . ?

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 C10 C11 C19 -0.75(17) . . . . ?
O2 C10 C11 C12 179.67(13) . . . . ?
O2 C10 C9 C8 179.50(14) . . . . ?
O2 C14 C15 C16 -178.76(14) . . . . ?
O1 C7 C8 C9 0.2(2) . . . . ?
O1 C7 C8 C13 -178.67(15) . . . . ?
N1 C5 C4 C7 -171.41(14) . . . . ?
N1 C5 C4 C3 3.6(2) . . . . ?
N1 C5 C6 F1 -154.67(14) . . . . ?
N1 C5 C6 F3 85.01(17) . . . . ?
N1 C5 C6 F2 -34.36(19) . . . . ?
C5 N1 C1 C2 -2.2(2) . . . . ?
C5 C4 C7 O1 64.3(2) . . . . ?
C5 C4 C7 C8 -117.35(17) . . . . ?
C5 C4 C3 C2 -3.0(2) . . . . ?
C10 O2 C14 C19 -0.12(16) . . . . ?
C10 O2 C14 C15 -179.82(15) . . . . ?
C10 C11 C19 C14 0.63(16) . . . . ?
C10 C11 C19 C18 -178.43(16) . . . . ?
C10 C11 C12 C13 1.0(2) . . . . ?
C10 C9 C8 C7 -178.14(13) . . . . ?
C10 C9 C8 C13 0.7(2) . . . . ?
C4 C5 C6 F1 25.7(2) . . . . ?
C4 C5 C6 F3 -94.61(17) . . . . ?
C4 C5 C6 F2 146.02(15) . . . . ?
C4 C7 C8 C9 -178.17(14) . . . . ?
C4 C7 C8 C13 3.0(2) . . . . ?
C4 C3 C2 C1 0.2(2) . . . . ?
C11 C10 C9 C8 -0.8(2) . . . . ?
C11 C19 C14 O2 -0.33(17) . . . . ?
C11 C19 C14 C15 179.37(14) . . . . ?
C11 C19 C18 C17 179.19(16) . . . . ?
C11 C12 C13 C8 -1.1(2) . . . . ?
C19 C11 C12 C13 -178.40(16) . . . . ?
C19 C14 C15 C16 1.6(2) . . . . ?
C14 O2 C10 C11 0.55(16) . . . . ?
C14 O2 C10 C9 -179.70(14) . . . . ?
C14 C19 C18 C17 0.2(2) . . . . ?
C7 C4 C3 C2 172.11(14) . . . . ?
C7 C8 C13 C12 179.00(14) . . . . ?
C9 C10 C11 C19 179.49(14) . . . . ?
C9 C10 C11 C12 -0.1(2) . . . . ?
C9 C8 C13 C12 0.2(2) . . . . ?
C3 C4 C7 O1 -110.54(18) . . . . ?
C3 C4 C7 C8 67.84(19) . . . . ?
C3 C2 C1 N1 2.6(3) . . . . ?
C6 C5 C4 C7 8.2(2) . . . . ?
C6 C5 C4 C3 -176.86(14) . . . . ?
C16 C17 C18 C19 0.6(2) . . . . ?
C17 C16 C15 C14 -0.7(2) . . . . ?
C1 N1 C5 C4 -1.0(2) . . . . ?
C1 N1 C5 C6 179.41(14) . . . . ?
C18 C19 C14 O2 178.91(13) . . . . ?
C18 C19 C14 C15 -1.4(2) . . . . ?
C12 C11 C19 C14 -179.89(17) . . . . ?
C12 C11 C19 C18 1.0(3) . . . . ?
C15 C16 C17 C18 -0.4(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 1.407
_oxdiff_exptl_absorpt_empirical_full_min 0.770
####################################################################### 
# 
# 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_s6734l
_database_code_depnum_ccdc_archive 'CCDC 2475751'
loop_
_audit_author_name
_audit_author_address
'Avantika Hasija'
;University of Manchester
United Kingdom
;
_audit_update_record             
;
2025-07-24 deposited with the CCDC.	2026-06-08 downloaded from the CCDC.
;
_audit_creation_date             2025-07-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7308)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 F3 N O2'
_chemical_formula_sum            'C20 H14 F3 N O2'
_chemical_formula_weight         357.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H14F3NO2
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      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                   8.3940(2)
_cell_length_b                   21.4396(5)
_cell_length_c                   9.3120(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.923(2)
_cell_angle_gamma                90
_cell_volume                     1675.62(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4035
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.5970
_cell_measurement_theta_min      5.1820
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.974
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.112a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 9 5 0.0254
0 -9 -5 0.0109
-5 1 0 0.0145
-5 1 0 0.0145
5 -1 0 0.0182
0 7 -5 0.0254
0 -7 5 0.0073

_exptl_crystal_size_max          0.049
_exptl_crystal_size_mid          0.033
_exptl_crystal_size_min          0.033
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.4767 9.1326 4.5223 -0.3952 0.9186 0.0008
-0.4767 -9.1326 -4.5223 0.3952 -0.9186 -0.0008
-5.4254 0.8292 0.4861 -0.0008 0.0005 -1.0000
-5.4257 0.8283 0.4807 -0.0000 0.0001 -1.0000
5.4257 -0.8283 -0.4807 0.0000 -0.0001 1.0000
-0.1287 7.1403 -5.1843 0.9958 0.0920 0.0000
0.1287 -7.1403 5.1843 -0.9958 -0.0920 -0.0000

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11328
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.359
_diffrn_reflns_theta_min         4.124
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -4.00  44.00   0.50    0.76    --   43.06  20.00-180.00   96
  2  ω     64.00 129.00   0.50    0.76    --   43.06  20.00-180.00  130
  3  ω     60.00 135.00   0.50    0.76    --   45.54  50.00 150.00  150
  4  ω    -44.00  43.00   0.50    0.76    --   45.54  50.00 150.00  174
  5  ω    156.00 198.00   0.50    4.00    --  108.20  60.00  30.00   84
  6  ω     19.00  77.00   0.50    4.00    --  108.20  60.00-150.00  116
  7  ω     19.00  54.00   0.50    4.00    --  108.20  60.00 150.00   70
  8  ω     36.00  63.00   0.50    4.00    --  108.20  60.00  30.00   54
  9  ω    165.00 197.00   0.50    4.00    --  108.20  60.00-150.00   64
 10  ω    104.00 153.00   0.50    4.00    --  108.20  60.00  30.00   98
 11  ω     80.00 137.00   0.50    4.00    --  108.20  60.00-150.00  114
 12  ω     59.00 197.00   0.50    4.00    --  108.20  60.00 150.00  276
 13  ω     88.00 113.00   0.50    4.00    --  108.20   0.00  90.00   50
 14  ω     37.00 136.00   0.50    4.00    --  108.20  20.00-150.00  198
 15  ω    172.00 198.00   0.50    4.00    --  108.20  20.00-150.00   52
 16  ω    118.00 198.00   0.50    4.00    --  108.20  40.00 -30.00  160
 17  ω     88.00 138.00   0.50    4.00    --  108.20  50.00 120.00  100
 18  ω    151.00 197.00   0.50    4.00    --  108.20  60.00-180.00   92
 19  ω     23.00  52.00   0.50    4.00    --  108.20   0.00  90.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0084764000
_diffrn_orient_matrix_UB_12      0.0310180000
_diffrn_orient_matrix_UB_13      -0.1491400000
_diffrn_orient_matrix_UB_21      0.0161364000
_diffrn_orient_matrix_UB_22      0.0646416000
_diffrn_orient_matrix_UB_23      0.0708796000
_diffrn_orient_matrix_UB_31      0.1827284000
_diffrn_orient_matrix_UB_32      -0.0042848000
_diffrn_orient_matrix_UB_33      -0.0104367000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2824
_reflns_number_total             3432
_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 1.171.43.112a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 44.112a 64-bit (release 21-05-2025))'
_computing_data_reduction        'CrysAlisPro 1.171.43.112a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0020(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3432
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0374
_refine_ls_restrained_S_all      1.051
_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)+(0.0434P)²+0.4646P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.1015
_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. Others
 Sof(F3)=Sof(F1)=Sof(F2)=1-FVAR(1)
 Sof(F6)=Sof(F5)=Sof(F4)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C1(H1), C13(H13), C15(H15), C11(H11), C19(H19), C18(H18), C9(H9),
 C12(H12), C2(H2), C10(H10)
3.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_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
F6 F 0.393(2) 0.6757(8) 0.7536(17) 0.056(4) Uani 0.34(6) 1 d . . P A 1
O1 O 0.20638(14) 0.46346(5) -0.04865(12) 0.0344(3) Uani 1 1 d . . . . .
O2 O 0.45886(12) 0.56875(5) 0.58292(11) 0.0300(2) Uani 1 1 d . . . . .
F5 F 0.6191(18) 0.7192(9) 0.7391(19) 0.049(3) Uani 0.34(6) 1 d . . P A 1
C4 C 0.41694(16) 0.66138(6) 0.45112(15) 0.0242(3) Uani 1 1 d . . . . .
C16 C 0.37682(17) 0.49924(6) 0.14900(15) 0.0256(3) Uani 1 1 d . . . . .
H16 H 0.420490 0.458873 0.164481 0.031 Uiso 1 1 calc R U . . .
C5 C 0.46820(17) 0.71475(7) 0.52374(16) 0.0281(3) Uani 1 1 d . . . . .
C14 C 0.36473(16) 0.60861(6) 0.21191(15) 0.0240(3) Uani 1 1 d . . . . .
C3 C 0.41720(16) 0.66253(6) 0.30021(16) 0.0253(3) Uani 1 1 d . . . . .
N1 N 0.51818(16) 0.76696(6) 0.46006(15) 0.0334(3) Uani 1 1 d . . . . .
C8 C 0.18709(16) 0.59498(6) 0.54814(14) 0.0235(3) Uani 1 1 d . . . . .
C1 C 0.5154(2) 0.76777(7) 0.31698(18) 0.0346(4) Uani 1 1 d . . . . .
H1 H 0.548521 0.804642 0.269415 0.042 Uiso 1 1 calc R U . . .
C13 C 0.13540(17) 0.54770(7) 0.63962(14) 0.0258(3) Uani 1 1 d . . . . .
H13 H 0.211039 0.521734 0.687479 0.031 Uiso 1 1 calc R U . . .
C15 C 0.42436(16) 0.54887(6) 0.23527(15) 0.0247(3) Uani 1 1 d . . . . .
H15 H 0.498819 0.541924 0.311510 0.030 Uiso 1 1 calc R U . . .
C20 C 0.2482(2) 0.40062(7) -0.01579(19) 0.0389(4) Uani 1 1 d . . . . .
H20A H 0.192482 0.372443 -0.082475 0.058 Uiso 1 1 calc R U . . .
H20B H 0.217507 0.390971 0.082831 0.058 Uiso 1 1 calc R U . . .
H20C H 0.363546 0.395225 -0.025109 0.058 Uiso 1 1 calc R U . . .
C7 C 0.36059(16) 0.60419(6) 0.53151(14) 0.0231(3) Uani 1 1 d . . . . .
C17 C 0.26474(17) 0.50908(7) 0.03969(15) 0.0270(3) Uani 1 1 d . . . . .
C11 C -0.13638(18) 0.57593(8) 0.58921(16) 0.0320(3) Uani 1 1 d . . . . .
H11 H -0.246967 0.569318 0.603143 0.038 Uiso 1 1 calc R U . . .
C19 C 0.25469(18) 0.61788(7) 0.09958(15) 0.0276(3) Uani 1 1 d . . . . .
H19 H 0.214514 0.658554 0.080886 0.033 Uiso 1 1 calc R U . . .
C18 C 0.20410(18) 0.56857(7) 0.01586(15) 0.0299(3) Uani 1 1 d . . . . .
H18 H 0.127316 0.575240 -0.058614 0.036 Uiso 1 1 calc R U . . .
C9 C 0.07529(17) 0.63263(7) 0.47751(15) 0.0277(3) Uani 1 1 d . . . . .
H9 H 0.109664 0.665007 0.415628 0.033 Uiso 1 1 calc R U . . .
C12 C -0.02518(18) 0.53868(7) 0.66052(16) 0.0300(3) Uani 1 1 d . . . . .
H12 H -0.059888 0.506904 0.723871 0.036 Uiso 1 1 calc R U . . .
C2 C 0.46656(18) 0.71752(7) 0.23458(17) 0.0303(3) Uani 1 1 d . . . . .
H2 H 0.466612 0.720446 0.132780 0.036 Uiso 1 1 calc R U . . .
F4 F 0.405(2) 0.7732(8) 0.730(2) 0.056(3) Uani 0.34(6) 1 d . . P A 1
C10 C -0.08613(18) 0.62277(8) 0.49766(16) 0.0321(3) Uani 1 1 d . . . . .
H10 H -0.162335 0.648113 0.448742 0.039 Uiso 1 1 calc R U . . .
C6 C 0.47500(19) 0.71950(7) 0.68567(18) 0.0330(3) Uani 1 1 d . . . . .
F3 F 0.3831(8) 0.6792(4) 0.7513(8) 0.0418(17) Uani 0.66(6) 1 d . . P A 2
F1 F 0.437(2) 0.7752(3) 0.7310(10) 0.0633(19) Uani 0.66(6) 1 d . . P A 2
F2 F 0.6228(11) 0.7085(9) 0.7352(11) 0.073(2) Uani 0.66(6) 1 d . . P A 2


_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
F6 C6 1.332(14) . ?
O1 C20 1.424(2) . ?
O1 C17 1.3639(18) . ?
O2 C7 1.2142(17) . ?
F5 C6 1.301(16) . ?
C4 C5 1.394(2) . ?
C4 C3 1.406(2) . ?
C4 C7 1.5162(19) . ?
C16 H16 0.9500 . ?
C16 C15 1.388(2) . ?
C16 C17 1.391(2) . ?
C5 N1 1.337(2) . ?
C5 C6 1.511(2) . ?
C14 C3 1.481(2) . ?
C14 C15 1.3910(19) . ?
C14 C19 1.398(2) . ?
C3 C2 1.394(2) . ?
N1 C1 1.332(2) . ?
C8 C13 1.3976(19) . ?
C8 C7 1.4803(19) . ?
C8 C9 1.395(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.381(2) . ?
C13 H13 0.9500 . ?
C13 C12 1.379(2) . ?
C15 H15 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C17 C18 1.390(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.389(2) . ?
C11 C10 1.387(2) . ?
C19 H19 0.9500 . ?
C19 C18 1.377(2) . ?
C18 H18 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.387(2) . ?
C12 H12 0.9500 . ?
C2 H2 0.9500 . ?
F4 C6 1.360(14) . ?
C10 H10 0.9500 . ?
C6 F3 1.315(6) . ?
C6 F1 1.308(8) . ?
C6 F2 1.338(11) . ?

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
C17 O1 C20 117.62(13) . . ?
C5 C4 C3 117.73(13) . . ?
C5 C4 C7 121.38(13) . . ?
C3 C4 C7 120.89(12) . . ?
C15 C16 H16 120.3 . . ?
C15 C16 C17 119.48(13) . . ?
C17 C16 H16 120.3 . . ?
C4 C5 C6 123.08(13) . . ?
N1 C5 C4 124.66(14) . . ?
N1 C5 C6 112.25(13) . . ?
C15 C14 C3 121.92(13) . . ?
C15 C14 C19 118.66(13) . . ?
C19 C14 C3 119.41(13) . . ?
C4 C3 C14 122.41(12) . . ?
C2 C3 C4 117.29(13) . . ?
C2 C3 C14 120.29(13) . . ?
C1 N1 C5 116.98(13) . . ?
C13 C8 C7 118.43(12) . . ?
C9 C8 C13 119.61(13) . . ?
C9 C8 C7 121.95(12) . . ?
N1 C1 H1 118.5 . . ?
N1 C1 C2 123.08(14) . . ?
C2 C1 H1 118.5 . . ?
C8 C13 H13 119.9 . . ?
C12 C13 C8 120.11(13) . . ?
C12 C13 H13 119.9 . . ?
C16 C15 C14 121.06(13) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
O1 C20 H20A 109.5 . . ?
O1 C20 H20B 109.5 . . ?
O1 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O2 C7 C4 119.04(12) . . ?
O2 C7 C8 122.58(13) . . ?
C8 C7 C4 118.35(12) . . ?
O1 C17 C16 124.39(13) . . ?
O1 C17 C18 115.76(13) . . ?
C18 C17 C16 119.84(13) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.08(14) . . ?
C14 C19 H19 119.7 . . ?
C18 C19 C14 120.56(13) . . ?
C18 C19 H19 119.7 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.37(14) . . ?
C19 C18 H18 119.8 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 119.96(13) . . ?
C10 C9 H9 120.0 . . ?
C13 C12 C11 120.18(14) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C3 C2 H2 119.9 . . ?
C1 C2 C3 120.25(14) . . ?
C1 C2 H2 119.9 . . ?
C11 C10 H10 120.0 . . ?
C9 C10 C11 120.05(14) . . ?
C9 C10 H10 120.0 . . ?
F6 C6 C5 114.5(7) . . ?
F6 C6 F4 103.0(11) . . ?
F5 C6 F6 107.6(10) . . ?
F5 C6 C5 113.6(8) . . ?
F5 C6 F4 107.1(11) . . ?
F4 C6 C5 110.3(9) . . ?
F3 C6 C5 114.0(3) . . ?
F3 C6 F2 105.8(6) . . ?
F1 C6 C5 112.2(5) . . ?
F1 C6 F3 107.6(7) . . ?
F1 C6 F2 106.2(6) . . ?
F2 C6 C5 110.6(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
O1 C17 C18 C19 179.73(13) . . . . ?
C4 C5 N1 C1 1.3(2) . . . . ?
C4 C5 C6 F6 -15.8(9) . . . . ?
C4 C5 C6 F5 108.3(9) . . . . ?
C4 C5 C6 F4 -131.4(10) . . . . ?
C4 C5 C6 F3 -21.1(5) . . . . ?
C4 C5 C6 F1 -143.7(10) . . . . ?
C4 C5 C6 F2 97.9(8) . . . . ?
C4 C3 C2 C1 1.1(2) . . . . ?
C16 C17 C18 C19 0.2(2) . . . . ?
C5 C4 C3 C14 -179.79(13) . . . . ?
C5 C4 C3 C2 -1.0(2) . . . . ?
C5 C4 C7 O2 -79.76(18) . . . . ?
C5 C4 C7 C8 98.28(16) . . . . ?
C5 N1 C1 C2 -1.1(2) . . . . ?
C14 C3 C2 C1 179.97(14) . . . . ?
C14 C19 C18 C17 -1.6(2) . . . . ?
C3 C4 C5 N1 -0.2(2) . . . . ?
C3 C4 C5 C6 -179.51(13) . . . . ?
C3 C4 C7 O2 101.06(16) . . . . ?
C3 C4 C7 C8 -80.90(16) . . . . ?
C3 C14 C15 C16 -178.31(13) . . . . ?
C3 C14 C19 C18 179.95(13) . . . . ?
N1 C5 C6 F6 164.8(9) . . . . ?
N1 C5 C6 F5 -71.1(9) . . . . ?
N1 C5 C6 F4 49.2(10) . . . . ?
N1 C5 C6 F3 159.5(4) . . . . ?
N1 C5 C6 F1 37.0(10) . . . . ?
N1 C5 C6 F2 -81.4(8) . . . . ?
N1 C1 C2 C3 -0.1(3) . . . . ?
C8 C13 C12 C11 0.9(2) . . . . ?
C8 C9 C10 C11 0.7(2) . . . . ?
C13 C8 C7 O2 7.3(2) . . . . ?
C13 C8 C7 C4 -170.70(12) . . . . ?
C13 C8 C9 C10 -0.4(2) . . . . ?
C15 C16 C17 O1 -178.10(13) . . . . ?
C15 C16 C17 C18 1.4(2) . . . . ?
C15 C14 C3 C4 -51.14(19) . . . . ?
C15 C14 C3 C2 130.08(15) . . . . ?
C15 C14 C19 C18 1.3(2) . . . . ?
C20 O1 C17 C16 7.9(2) . . . . ?
C20 O1 C17 C18 -171.56(13) . . . . ?
C7 C4 C5 N1 -179.44(13) . . . . ?
C7 C4 C5 C6 1.3(2) . . . . ?
C7 C4 C3 C14 -0.6(2) . . . . ?
C7 C4 C3 C2 178.23(13) . . . . ?
C7 C8 C13 C12 178.44(13) . . . . ?
C7 C8 C9 C10 -179.21(13) . . . . ?
C17 C16 C15 C14 -1.6(2) . . . . ?
C19 C14 C3 C4 130.28(15) . . . . ?
C19 C14 C3 C2 -48.49(19) . . . . ?
C19 C14 C15 C16 0.3(2) . . . . ?
C9 C8 C13 C12 -0.4(2) . . . . ?
C9 C8 C7 O2 -173.89(14) . . . . ?
C9 C8 C7 C4 8.15(19) . . . . ?
C12 C11 C10 C9 -0.2(2) . . . . ?
C10 C11 C12 C13 -0.6(2) . . . . ?
C6 C5 N1 C1 -179.36(14) . . . . ?

_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 1.400
_oxdiff_exptl_absorpt_empirical_full_min 0.729
####################################################################### 
# 
# 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_s6735r
_database_code_depnum_ccdc_archive 'CCDC 2475672'
loop_
_audit_author_name
_audit_author_address
'Avantika Hasija'
;University of Manchester
United Kingdom
;
_audit_update_record             
;
2025-07-24 deposited with the CCDC.	2026-06-08 downloaded from the CCDC.
;
_audit_creation_date             2025-07-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7308)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H14 F3 N O S'
_chemical_formula_sum            'C25 H14 F3 N O S'
_chemical_formula_weight         433.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         C25H14F3NOS
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'
S S 0.3331 0.5567 '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                   8.36426(13)
_cell_length_b                   25.5739(4)
_cell_length_c                   9.21252(14)
_cell_angle_alpha                90
_cell_angle_beta                 91.2344(14)
_cell_angle_gamma                90
_cell_volume                     1970.16(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7282
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.7400
_cell_measurement_theta_min      3.4670
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.867
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.874
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.112a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             888
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -16 1 0.0461
1 16 0 0.0301
2 1 6 0.0327
-2 -2 -6 0.0187
1 -16 0 0.0385
0 -8 -5 0.0342
-1 16 0 0.0359
-4 -1 4 0.0489
-5 6 -1 0.0528
5 -4 -1 0.0377

_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.053
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.7829 -16.1421 1.1115 -0.7014 -0.3865 0.5989
1.0060 16.2877 -0.3473 0.7663 0.4212 -0.4852
1.6579 1.2720 5.6333 0.4880 0.2610 0.8329
-1.7055 -2.2020 -5.5781 -0.5291 -0.2836 -0.7997
0.9632 -16.3220 0.2507 -0.5099 -0.6724 0.5366
-0.0103 -7.7164 -5.2916 -0.5117 -0.6646 -0.5445
-0.9718 16.2991 -0.3653 0.5034 0.6641 -0.5528
-4.1431 -0.6671 3.9521 -0.4241 0.7826 0.4557
-4.9707 6.3613 -0.6462 -0.4326 0.7876 -0.4387
5.1468 -3.7223 -1.4858 0.4784 -0.8761 0.0601

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            12451
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.990
_diffrn_reflns_theta_min         3.456
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     48.00  74.00   0.50    0.12    --  107.75 -77.00-150.00   52
  2  ω     89.00 114.00   0.50    0.12    --  107.75 -77.00-150.00   50
  3  ω    117.00 143.00   0.50    0.12    --  107.75  84.00 101.00   52
  4  ω     36.00  73.00   0.50    0.12    --  107.75 -61.00 150.00   74
  5  ω     35.00  72.00   0.50    0.12    --  107.75 -61.00 120.00   74
  6  ω     41.00 118.00   0.50    0.05    --   46.87  38.00-180.00  154
  7  ω     35.00  60.00   0.50    0.12    --  107.75 -61.00-180.00   50
  8  ω     35.00  74.00   0.50    0.12    --  107.75-125.00-150.00   78
  9  ω     81.00 110.00   0.50    0.12    --  107.75-125.00-150.00   58
 10  ω     40.00  87.00   0.50    0.12    --  107.75 -84.00 -18.00   94
 11  ω     14.00  45.00   0.50    0.05    --   46.87 -84.00 -18.00   62
 12  ω    -22.00  29.00   0.50    0.05    --  -46.87  19.00 -90.00  102
 13  ω   -112.00 -37.00   0.50    0.12    -- -109.00  77.00 -60.00  150
 14  ω    -71.00 -38.00   0.50    0.12    -- -109.00  61.00  60.00   66
 15  ω    -71.00 -46.00   0.50    0.12    -- -109.00  61.00  30.00   50
 16  ω    -67.00 -39.00   0.50    0.12    -- -109.00  61.00  90.00   56
 17  ω    -71.00 -43.00   0.50    0.12    -- -109.00  61.00 120.00   56
 18  ω    -22.00  29.00   0.50    0.05    --  -46.87  19.00  30.00  102
 19  ω    -64.00  24.00   0.50    0.05    --  -46.87  84.00 101.00  176
 20  ω   -105.00 -79.00   0.50    0.12    -- -109.00  84.00 101.00   52
 21  ω   -172.00 -95.00   0.50    0.12    -- -109.00 -15.00-180.00  154
 22  ω   -164.00 -90.00   0.50    0.12    -- -109.00 -84.00 -18.00  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1327833000
_diffrn_orient_matrix_UB_12      0.0396688000
_diffrn_orient_matrix_UB_13      0.0385982000
_diffrn_orient_matrix_UB_21      -0.1232938000
_diffrn_orient_matrix_UB_22      0.0350660000
_diffrn_orient_matrix_UB_23      0.0746996000
_diffrn_orient_matrix_UB_31      0.0326864000
_diffrn_orient_matrix_UB_32      -0.0287226000
_diffrn_orient_matrix_UB_33      0.1447164000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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                3333
_reflns_number_total             4032
_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 1.171.43.112a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 44.117a 64-bit (release 07-07-2025))'
_computing_data_reduction        'CrysAlisPro 1.171.43.112a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4032
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0375
_refine_ls_restrained_S_all      1.048
_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)+(0.0373P)²+0.5699P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0943
_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:
 C8(H8), C25(H25), C21(H21), C2(H2), C14(H14), C24(H24), C5(H5), C11(H11),
 C3(H3), C22(H22), C10(H10), C4(H4), C15(H15), C23(H23)
;
_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
S1 S 0.36720(5) 0.50957(2) 1.15417(4) 0.02441(12) Uani 1 1 d . . . . .
F2 F 0.19797(13) 0.31053(4) 0.34017(11) 0.0305(2) Uani 1 1 d . . . . .
F1 F 0.16833(19) 0.22820(4) 0.36676(13) 0.0461(3) Uani 1 1 d . . . . .
O1 O 0.12251(14) 0.40291(5) 0.50784(13) 0.0239(3) Uani 1 1 d . . . . .
F3 F -0.03779(15) 0.27811(5) 0.35052(14) 0.0456(3) Uani 1 1 d . . . . .
N1 N 0.05981(19) 0.23671(6) 0.63549(18) 0.0284(3) Uani 1 1 d . . . . .
C8 C 0.16022(19) 0.42071(6) 0.85415(18) 0.0200(3) Uani 1 1 d . . . . .
H8 H 0.089228 0.426743 0.774025 0.024 Uiso 1 1 calc R U . . .
C20 C 0.3945(2) 0.38156(6) 0.55230(17) 0.0202(3) Uani 1 1 d . . . . .
C19 C 0.2194(2) 0.37323(6) 0.56289(17) 0.0189(3) Uani 1 1 d . . . . .
C17 C 0.16203(19) 0.32518(6) 0.64347(18) 0.0207(3) Uani 1 1 d . . . . .
C25 C 0.4480(2) 0.42527(7) 0.47598(19) 0.0252(4) Uani 1 1 d . . . . .
H25 H 0.372833 0.449564 0.436649 0.030 Uiso 1 1 calc R U . . .
C13 C 0.15940(19) 0.32481(6) 0.79646(19) 0.0216(3) Uani 1 1 d . . . . .
C9 C 0.2125(2) 0.37012(6) 0.88590(18) 0.0212(3) Uani 1 1 d . . . . .
C18 C 0.1104(2) 0.27451(7) 0.4076(2) 0.0272(4) Uani 1 1 d . . . . .
C21 C 0.5062(2) 0.34657(7) 0.61186(19) 0.0241(4) Uani 1 1 d . . . . .
H21 H 0.470959 0.317027 0.664888 0.029 Uiso 1 1 calc R U . . .
C2 C 0.2474(2) 0.60233(7) 1.02957(19) 0.0254(4) Uani 1 1 d . . . . .
H2 H 0.302574 0.622482 1.101368 0.030 Uiso 1 1 calc R U . . .
C7 C 0.21233(19) 0.46228(6) 0.94012(17) 0.0199(3) Uani 1 1 d . . . . .
C16 C 0.1116(2) 0.28020(7) 0.5711(2) 0.0243(4) Uani 1 1 d . . . . .
C6 C 0.1785(2) 0.51759(6) 0.92306(18) 0.0204(3) Uani 1 1 d . . . . .
C14 C 0.1084(2) 0.27890(7) 0.8630(2) 0.0267(4) Uani 1 1 d . . . . .
H14 H 0.106872 0.276741 0.965886 0.032 Uiso 1 1 calc R U . . .
C12 C 0.3150(2) 0.45243(7) 1.06070(18) 0.0214(3) Uani 1 1 d . . . . .
C24 C 0.6091(2) 0.43321(8) 0.4577(2) 0.0303(4) Uani 1 1 d . . . . .
H24 H 0.644493 0.462727 0.404653 0.036 Uiso 1 1 calc R U . . .
C5 C 0.0839(2) 0.54247(7) 0.81701(18) 0.0212(3) Uani 1 1 d . . . . .
H5 H 0.027765 0.522495 0.745449 0.025 Uiso 1 1 calc R U . . .
C11 C 0.3671(2) 0.40198(7) 1.09316(19) 0.0245(4) Uani 1 1 d . . . . .
H11 H 0.436585 0.395669 1.174162 0.029 Uiso 1 1 calc R U . . .
C1 C 0.2571(2) 0.54799(7) 1.02950(18) 0.0215(3) Uani 1 1 d . . . . .
C3 C 0.1552(2) 0.62616(7) 0.9220(2) 0.0258(4) Uani 1 1 d . . . . .
H3 H 0.147896 0.663217 0.919504 0.031 Uiso 1 1 calc R U . . .
C22 C 0.6683(2) 0.35488(8) 0.5937(2) 0.0295(4) Uani 1 1 d . . . . .
H22 H 0.743895 0.330963 0.634144 0.035 Uiso 1 1 calc R U . . .
C10 C 0.3159(2) 0.36139(7) 1.00568(19) 0.0235(4) Uani 1 1 d . . . . .
H10 H 0.351073 0.326842 1.026694 0.028 Uiso 1 1 calc R U . . .
C4 C 0.0726(2) 0.59665(7) 0.81708(19) 0.0246(4) Uani 1 1 d . . . . .
H4 H 0.008298 0.613767 0.745313 0.029 Uiso 1 1 calc R U . . .
C15 C 0.0603(2) 0.23667(7) 0.7800(2) 0.0305(4) Uani 1 1 d . . . . .
H15 H 0.025829 0.206001 0.828344 0.037 Uiso 1 1 calc R U . . .
C23 C 0.7206(2) 0.39814(8) 0.5165(2) 0.0308(4) Uani 1 1 d . . . . .
H23 H 0.831706 0.403783 0.503935 0.037 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
S1 C12 1.7467(17) . ?
S1 C1 1.7570(17) . ?
F2 C18 1.338(2) . ?
F1 C18 1.337(2) . ?
O1 C19 1.214(2) . ?
F3 C18 1.339(2) . ?
N1 C16 1.337(2) . ?
N1 C15 1.331(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.395(2) . ?
C8 C7 1.390(2) . ?
C20 C19 1.485(2) . ?
C20 C25 1.399(2) . ?
C20 C21 1.397(2) . ?
C19 C17 1.519(2) . ?
C17 C13 1.410(2) . ?
C17 C16 1.391(2) . ?
C25 H25 0.9500 . ?
C25 C24 1.377(3) . ?
C13 C9 1.484(2) . ?
C13 C14 1.395(2) . ?
C9 C10 1.405(2) . ?
C18 C16 1.513(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.386(3) . ?
C2 H2 0.9500 . ?
C2 C1 1.392(2) . ?
C2 C3 1.384(3) . ?
C7 C6 1.450(2) . ?
C7 C12 1.412(2) . ?
C6 C5 1.397(2) . ?
C6 C1 1.404(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.378(3) . ?
C12 C11 1.392(2) . ?
C24 H24 0.9500 . ?
C24 C23 1.395(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.389(2) . ?
C11 H11 0.9500 . ?
C11 C10 1.377(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.397(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.391(3) . ?
C10 H10 0.9500 . ?
C4 H4 0.9500 . ?
C15 H15 0.9500 . ?
C23 H23 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
C12 S1 C1 91.36(8) . . ?
C15 N1 C16 116.76(16) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C7 C8 C9 119.80(15) . . ?
C25 C20 C19 118.30(15) . . ?
C21 C20 C19 122.29(15) . . ?
C21 C20 C25 119.38(16) . . ?
O1 C19 C20 122.25(15) . . ?
O1 C19 C17 119.66(15) . . ?
C20 C19 C17 118.08(14) . . ?
C13 C17 C19 120.38(14) . . ?
C16 C17 C19 122.04(15) . . ?
C16 C17 C13 117.58(16) . . ?
C20 C25 H25 119.9 . . ?
C24 C25 C20 120.25(17) . . ?
C24 C25 H25 119.9 . . ?
C17 C13 C9 122.60(15) . . ?
C14 C13 C17 117.13(16) . . ?
C14 C13 C9 120.25(16) . . ?
C8 C9 C13 121.28(15) . . ?
C8 C9 C10 119.79(16) . . ?
C10 C9 C13 118.92(15) . . ?
F2 C18 F3 106.37(14) . . ?
F2 C18 C16 113.83(14) . . ?
F1 C18 F2 105.90(16) . . ?
F1 C18 F3 106.76(15) . . ?
F1 C18 C16 111.76(15) . . ?
F3 C18 C16 111.74(16) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.13(17) . . ?
C22 C21 H21 119.9 . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C3 C2 C1 118.08(16) . . ?
C8 C7 C6 128.75(15) . . ?
C8 C7 C12 119.32(15) . . ?
C12 C7 C6 111.91(15) . . ?
N1 C16 C17 124.95(17) . . ?
N1 C16 C18 111.51(15) . . ?
C17 C16 C18 123.54(16) . . ?
C5 C6 C7 128.78(15) . . ?
C5 C6 C1 119.07(15) . . ?
C1 C6 C7 112.14(15) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.27(17) . . ?
C15 C14 H14 119.9 . . ?
C7 C12 S1 112.33(12) . . ?
C11 C12 S1 126.58(13) . . ?
C11 C12 C7 121.08(15) . . ?
C25 C24 H24 119.8 . . ?
C25 C24 C23 120.37(18) . . ?
C23 C24 H24 119.8 . . ?
C6 C5 H5 120.3 . . ?
C4 C5 C6 119.44(16) . . ?
C4 C5 H5 120.3 . . ?
C12 C11 H11 120.6 . . ?
C10 C11 C12 118.76(15) . . ?
C10 C11 H11 120.6 . . ?
C2 C1 S1 125.99(13) . . ?
C2 C1 C6 121.79(16) . . ?
C6 C1 S1 112.20(13) . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.16(16) . . ?
C4 C3 H3 119.4 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.19(17) . . ?
C23 C22 H22 119.9 . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.22(16) . . ?
C11 C10 H10 119.4 . . ?
C5 C4 C3 120.43(16) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
N1 C15 C14 123.29(17) . . ?
N1 C15 H15 118.4 . . ?
C14 C15 H15 118.4 . . ?
C24 C23 H23 120.2 . . ?
C22 C23 C24 119.66(17) . . ?
C22 C23 H23 120.2 . . ?

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
S1 C12 C11 C10 -178.79(14) . . . . ?
F2 C18 C16 N1 -163.57(15) . . . . ?
F2 C18 C16 C17 15.9(2) . . . . ?
F1 C18 C16 N1 -43.7(2) . . . . ?
F1 C18 C16 C17 135.80(17) . . . . ?
O1 C19 C17 C13 -101.29(18) . . . . ?
O1 C19 C17 C16 79.1(2) . . . . ?
F3 C18 C16 N1 75.91(19) . . . . ?
F3 C18 C16 C17 -104.64(19) . . . . ?
C8 C9 C10 C11 0.0(3) . . . . ?
C8 C7 C6 C5 0.8(3) . . . . ?
C8 C7 C6 C1 -178.09(17) . . . . ?
C8 C7 C12 S1 179.83(13) . . . . ?
C8 C7 C12 C11 1.2(3) . . . . ?
C20 C19 C17 C13 79.80(19) . . . . ?
C20 C19 C17 C16 -99.76(18) . . . . ?
C20 C25 C24 C23 -0.8(3) . . . . ?
C20 C21 C22 C23 0.2(3) . . . . ?
C19 C20 C25 C24 -176.97(16) . . . . ?
C19 C20 C21 C22 177.22(16) . . . . ?
C19 C17 C13 C9 -0.5(2) . . . . ?
C19 C17 C13 C14 -178.66(15) . . . . ?
C19 C17 C16 N1 180.00(16) . . . . ?
C19 C17 C16 C18 0.6(3) . . . . ?
C17 C13 C9 C8 47.8(2) . . . . ?
C17 C13 C9 C10 -133.00(18) . . . . ?
C17 C13 C14 C15 -1.3(3) . . . . ?
C25 C20 C19 O1 0.0(2) . . . . ?
C25 C20 C19 C17 178.89(15) . . . . ?
C25 C20 C21 C22 -0.8(3) . . . . ?
C25 C24 C23 C22 0.2(3) . . . . ?
C13 C17 C16 N1 0.4(3) . . . . ?
C13 C17 C16 C18 -178.95(16) . . . . ?
C13 C9 C10 C11 -179.20(16) . . . . ?
C13 C14 C15 N1 0.3(3) . . . . ?
C9 C8 C7 C6 177.21(16) . . . . ?
C9 C8 C7 C12 -1.4(2) . . . . ?
C9 C13 C14 C15 -179.48(16) . . . . ?
C21 C20 C19 O1 -178.02(16) . . . . ?
C21 C20 C19 C17 0.9(2) . . . . ?
C21 C20 C25 C24 1.1(3) . . . . ?
C21 C22 C23 C24 0.1(3) . . . . ?
C2 C3 C4 C5 -1.2(3) . . . . ?
C7 C8 C9 C13 -179.97(16) . . . . ?
C7 C8 C9 C10 0.8(2) . . . . ?
C7 C6 C5 C4 -177.31(16) . . . . ?
C7 C6 C1 S1 -1.93(18) . . . . ?
C7 C6 C1 C2 176.92(15) . . . . ?
C7 C12 C11 C10 -0.3(3) . . . . ?
C16 N1 C15 C14 1.1(3) . . . . ?
C16 C17 C13 C9 179.10(15) . . . . ?
C16 C17 C13 C14 0.9(2) . . . . ?
C6 C7 C12 S1 1.00(18) . . . . ?
C6 C7 C12 C11 -177.66(16) . . . . ?
C6 C5 C4 C3 0.1(3) . . . . ?
C14 C13 C9 C8 -134.10(18) . . . . ?
C14 C13 C9 C10 45.1(2) . . . . ?
C12 S1 C1 C2 -176.68(16) . . . . ?
C12 S1 C1 C6 2.12(14) . . . . ?
C12 C7 C6 C5 179.44(17) . . . . ?
C12 C7 C6 C1 0.6(2) . . . . ?
C12 C11 C10 C9 -0.3(3) . . . . ?
C5 C6 C1 S1 179.10(13) . . . . ?
C5 C6 C1 C2 -2.0(3) . . . . ?
C1 S1 C12 C7 -1.77(14) . . . . ?
C1 S1 C12 C11 176.80(17) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C1 C6 C5 C4 1.5(2) . . . . ?
C3 C2 C1 S1 179.66(14) . . . . ?
C3 C2 C1 C6 1.0(3) . . . . ?
C15 N1 C16 C17 -1.4(3) . . . . ?
C15 N1 C16 C18 178.02(16) . . . . ?

_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 1.187
_oxdiff_exptl_absorpt_empirical_full_min 0.860
####################################################################### 
# 
# 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_s6782r
_database_code_depnum_ccdc_archive 'CCDC 2515794'
loop_
_audit_author_name
_audit_author_address
' Avantika Hasija'
;The University of Manchester
United Kingdom
;
_audit_update_record             
;
2025-12-14 deposited with the CCDC.	2026-06-08 downloaded from the CCDC.
;
_audit_creation_date             2025-11-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H10 Cl F2 N O2'
_chemical_formula_sum            'C14 H10 Cl F2 N O2'
_chemical_formula_weight         297.68
_chemical_melting_point          ?
_chemical_oxdiff_formula         C14H10ClF2NO2
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      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                   10.69639(17)
_cell_length_b                   11.34198(17)
_cell_length_c                   21.1345(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2564.00(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6979
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.1500
_cell_measurement_theta_min      2.0990
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.896
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.608
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.112a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 -7 2 0.1309
-2 1 -2 0.0512
1 -1 2 0.0468
-1 -2 1 0.1300
1 2 0 0.1025
0 0 1 0.0517
0 0 -1 0.0272
2 1 -2 0.0891
3 -6 -7 0.0790
-5 0 10 0.0979
-3 6 7 0.1318
6 -3 -6 0.0552
5 0 10 0.0672

_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.079
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2.5119 -6.7501 2.2587 0.1285 -0.0666 0.9895
-2.0000 1.0000 -2.0000 -0.2807 0.2094 0.0055
1.0000 -1.0000 2.0000 0.2152 -0.1010 0.0630
-1.0000 -2.0000 1.0000 0.0424 0.0194 0.3127
1.0000 2.0000 -0.0000 0.0214 0.0152 -0.3065
-0.0000 -0.0000 1.0000 0.0638 0.0346 0.0062
0.0000 0.0000 -1.0000 -0.0638 -0.0346 -0.0062
2.0000 1.0000 -2.0000 -0.0188 -0.2242 -0.2684
3.0000 -6.0000 -7.0000 -0.1183 -0.9382 0.4651
-5.0000 0.0000 10.0000 0.3111 0.8880 0.4047
-3.0000 6.0000 7.0000 0.1183 0.9382 -0.4651
6.0000 -3.0000 -6.0000 0.0758 -1.0434 -0.0912
5.0000 -0.0000 10.0000 0.9658 -0.1961 -0.2800

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9507
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.911
_diffrn_reflns_theta_min         4.184
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     64.00 105.00   0.50    0.05    --  107.75 -95.00-120.00   82
  2  ω     46.00  75.00   0.50    0.05    --  107.75-124.00 169.00   58
  3  ω    -21.00  24.00   0.50    0.05    --  -46.51  19.00-120.00   90
  4  ω     -9.00  29.00   0.50    0.05    --  -46.51  19.00 -90.00   76
  5  ω    -16.00  20.00   0.50    0.05    --  -46.51  19.00   0.00   72
  6  ω    -68.00 -42.00   0.50    0.05    -- -109.00  61.00-150.00   52
  7  ω    -71.00 -39.00   0.50    0.05    -- -109.00  61.00-180.00   64
  8  ω   -109.00 -83.00   0.50    0.05    -- -109.00 124.00-112.00   52
  9  ω   -102.00 -71.00   0.50    0.05    --  -46.51 148.00  52.00   62
 10  ω    -67.00 -41.00   0.50    0.05    --  -46.51 148.00  52.00   52
 11  ω    -64.00 -36.00   0.50    0.05    -- -109.00 124.00-112.00   56
 12  ω   -166.00-140.00   0.50    0.05    -- -109.00 -38.00  32.00   52
 13  ω     35.00  65.00   0.50    0.05    --  107.75 -61.00 -60.00   60
 14  ω     37.00  72.00   0.50    0.05    --  107.75 -61.00  30.00   70
 15  ω     60.00 113.00   0.50    0.05    --  107.75 -77.00 120.00  106
 16  ω     97.00 175.00   0.50    0.05    --  107.75  84.00   1.00  156
 17  ω    -18.00  24.00   0.50    0.05    --   46.51 -19.00 -90.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0654685000
_diffrn_orient_matrix_UB_12      -0.0220299000
_diffrn_orient_matrix_UB_13      0.0638436000
_diffrn_orient_matrix_UB_21      -0.1084094000
_diffrn_orient_matrix_UB_22      0.0617893000
_diffrn_orient_matrix_UB_23      0.0345991000
_diffrn_orient_matrix_UB_31      -0.0684724000
_diffrn_orient_matrix_UB_32      -0.1190202000
_diffrn_orient_matrix_UB_33      0.0062333000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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                2375
_reflns_number_total             2640
_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 1.171.43.112a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 44.122a 64-bit (release 14-09-2025))'
_computing_data_reduction        'CrysAlisPro 1.171.43.112a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2640
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0296
_refine_ls_restrained_S_all      1.085
_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)+(0.0394P)²+0.9990P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0779
_refine_ls_wR_factor_ref         0.0799
_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:
 C13(H13), C9(H9), C12(H12), C10(H10), C4(H4), C3(H3), C5(H5)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_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 0.56887(3) 0.60331(3) 0.67733(2) 0.02657(11) Uani 1 1 d . . . . .
F2 F 0.55307(9) 0.48728(7) 0.57534(4) 0.0306(2) Uani 1 1 d . . . . .
F1 F 0.39789(8) 0.60293(7) 0.59456(4) 0.0284(2) Uani 1 1 d . . . . .
O2 O 0.51761(9) 0.04231(8) 0.37375(4) 0.0204(2) Uani 1 1 d . . . . .
O1 O 0.65242(9) 0.27128(9) 0.63909(5) 0.0254(2) Uani 1 1 d . . . . .
N1 N 0.30688(11) 0.46225(10) 0.68593(5) 0.0180(2) Uani 1 1 d . . . . .
C13 C 0.64208(12) 0.14544(11) 0.52219(6) 0.0174(3) Uani 1 1 d . . . . .
H13 H 0.718188 0.139622 0.545142 0.021 Uiso 1 1 calc R U . . .
C11 C 0.51977(13) 0.10098(11) 0.42982(6) 0.0164(3) Uani 1 1 d . . . . .
C1 C 0.40461(12) 0.42522(11) 0.65178(6) 0.0160(3) Uani 1 1 d . . . . .
C9 C 0.43092(12) 0.21684(12) 0.51313(6) 0.0177(3) Uani 1 1 d . . . . .
H9 H 0.362168 0.259096 0.530328 0.021 Uiso 1 1 calc R U . . .
C12 C 0.63144(12) 0.09199(11) 0.46393(6) 0.0178(3) Uani 1 1 d . . . . .
H12 H 0.699895 0.049062 0.446912 0.021 Uiso 1 1 calc R U . . .
C10 C 0.41937(12) 0.16488(11) 0.45404(6) 0.0181(3) Uani 1 1 d . . . . .
H10 H 0.344227 0.172735 0.430450 0.022 Uiso 1 1 calc R U . . .
C4 C 0.25429(13) 0.25961(12) 0.70469(6) 0.0185(3) Uani 1 1 d . . . . .
H4 H 0.199424 0.203764 0.723429 0.022 Uiso 1 1 calc R U . . .
C2 C 0.43592(12) 0.30707(11) 0.64275(6) 0.0153(3) Uani 1 1 d . . . . .
C8 C 0.54139(12) 0.20832(11) 0.54782(6) 0.0158(3) Uani 1 1 d . . . . .
C7 C 0.55368(12) 0.26394(11) 0.61056(6) 0.0171(3) Uani 1 1 d . . . . .
C3 C 0.35546(13) 0.22317(11) 0.66909(6) 0.0178(3) Uani 1 1 d . . . . .
H3 H 0.370316 0.141499 0.662527 0.021 Uiso 1 1 calc R U . . .
C5 C 0.23461(13) 0.37982(12) 0.71245(6) 0.0185(3) Uani 1 1 d . . . . .
H5 H 0.166318 0.404686 0.737905 0.022 Uiso 1 1 calc R U . . .
C6 C 0.47644(13) 0.52533(12) 0.62149(6) 0.0199(3) Uani 1 1 d . . . . .
C14 C 0.40493(14) 0.04673(13) 0.33746(7) 0.0247(3) Uani 1 1 d . . . . .
H14A H 0.415756 0.001160 0.298445 0.037 Uiso 1 1 calc R U . . .
H14B H 0.385679 0.128852 0.326837 0.037 Uiso 1 1 calc R U . . .
H14C H 0.336099 0.013195 0.362215 0.037 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
Cl1 C6 1.7756(14) . ?
F2 C6 1.3451(16) . ?
F1 C6 1.3433(16) . ?
O2 C11 1.3593(15) . ?
O2 C14 1.4295(17) . ?
O1 C7 1.2191(16) . ?
N1 C1 1.3381(17) . ?
N1 C5 1.3362(18) . ?
C13 H13 0.9500 . ?
C13 C12 1.3771(19) . ?
C13 C8 1.4007(18) . ?
C11 C12 1.3988(19) . ?
C11 C10 1.3931(18) . ?
C1 C2 1.3944(18) . ?
C1 C6 1.5129(18) . ?
C9 H9 0.9500 . ?
C9 C10 1.3865(19) . ?
C9 C8 1.3939(18) . ?
C12 H12 0.9500 . ?
C10 H10 0.9500 . ?
C4 H4 0.9500 . ?
C4 C3 1.3813(19) . ?
C4 C5 1.3893(18) . ?
C2 C7 1.5128(18) . ?
C2 C3 1.3986(18) . ?
C8 C7 1.4742(18) . ?
C3 H3 0.9500 . ?
C5 H5 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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
C11 O2 C14 117.71(11) . . ?
C5 N1 C1 117.30(11) . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C8 120.43(12) . . ?
C8 C13 H13 119.8 . . ?
O2 C11 C12 115.35(11) . . ?
O2 C11 C10 124.18(12) . . ?
C10 C11 C12 120.46(12) . . ?
N1 C1 C2 124.27(12) . . ?
N1 C1 C6 112.92(11) . . ?
C2 C1 C6 122.78(12) . . ?
C10 C9 H9 119.3 . . ?
C10 C9 C8 121.32(12) . . ?
C8 C9 H9 119.3 . . ?
C13 C12 C11 119.94(12) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C11 C10 H10 120.5 . . ?
C9 C10 C11 118.91(12) . . ?
C9 C10 H10 120.5 . . ?
C3 C4 H4 120.8 . . ?
C3 C4 C5 118.47(12) . . ?
C5 C4 H4 120.8 . . ?
C1 C2 C7 124.90(12) . . ?
C1 C2 C3 116.85(12) . . ?
C3 C2 C7 118.12(11) . . ?
C13 C8 C7 119.81(12) . . ?
C9 C8 C13 118.93(12) . . ?
C9 C8 C7 121.26(12) . . ?
O1 C7 C2 118.48(12) . . ?
O1 C7 C8 123.46(12) . . ?
C8 C7 C2 117.95(11) . . ?
C4 C3 C2 119.69(12) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
N1 C5 C4 123.33(12) . . ?
N1 C5 H5 118.3 . . ?
C4 C5 H5 118.3 . . ?
F2 C6 Cl1 107.60(9) . . ?
F2 C6 C1 112.05(11) . . ?
F1 C6 Cl1 107.66(9) . . ?
F1 C6 F2 106.51(11) . . ?
F1 C6 C1 110.69(11) . . ?
C1 C6 Cl1 112.05(9) . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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 C11 C12 C13 -178.17(12) . . . . ?
O2 C11 C10 C9 177.22(12) . . . . ?
N1 C1 C2 C7 -172.81(12) . . . . ?
N1 C1 C2 C3 3.05(19) . . . . ?
N1 C1 C6 Cl1 74.64(13) . . . . ?
N1 C1 C6 F2 -164.29(11) . . . . ?
N1 C1 C6 F1 -45.55(15) . . . . ?
C13 C8 C7 O1 9.4(2) . . . . ?
C13 C8 C7 C2 -166.64(12) . . . . ?
C1 N1 C5 C4 -1.87(19) . . . . ?
C1 C2 C7 O1 74.05(18) . . . . ?
C1 C2 C7 C8 -109.74(14) . . . . ?
C1 C2 C3 C4 -3.10(18) . . . . ?
C9 C8 C7 O1 -170.69(13) . . . . ?
C9 C8 C7 C2 13.30(18) . . . . ?
C12 C13 C8 C9 -0.63(19) . . . . ?
C12 C13 C8 C7 179.31(12) . . . . ?
C12 C11 C10 C9 -1.61(19) . . . . ?
C10 C11 C12 C13 0.75(19) . . . . ?
C10 C9 C8 C13 -0.3(2) . . . . ?
C10 C9 C8 C7 179.80(12) . . . . ?
C2 C1 C6 Cl1 -107.38(13) . . . . ?
C2 C1 C6 F2 13.69(18) . . . . ?
C2 C1 C6 F1 132.43(13) . . . . ?
C8 C13 C12 C11 0.39(19) . . . . ?
C8 C9 C10 C11 1.4(2) . . . . ?
C7 C2 C3 C4 173.05(12) . . . . ?
C3 C4 C5 N1 1.7(2) . . . . ?
C3 C2 C7 O1 -101.76(15) . . . . ?
C3 C2 C7 C8 74.45(16) . . . . ?
C5 N1 C1 C2 -0.60(19) . . . . ?
C5 N1 C1 C6 177.35(11) . . . . ?
C5 C4 C3 C2 0.9(2) . . . . ?
C6 C1 C2 C7 9.4(2) . . . . ?
C6 C1 C2 C3 -174.70(12) . . . . ?
C14 O2 C11 C12 178.89(11) . . . . ?
C14 O2 C11 C10 0.01(18) . . . . ?

_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 1.250
_oxdiff_exptl_absorpt_empirical_full_min 0.861
####################################################################### 
# 
# 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_s6747l
_database_code_depnum_ccdc_archive 'CCDC 2487299'
loop_
_audit_author_name
_audit_author_address
'Avantika Hasija'
;The University of Manchester
United Kingdom
;
_audit_update_record             
;
2025-09-11 deposited with the CCDC.	2026-06-08 downloaded from the CCDC.
;
_audit_creation_date             2025-09-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H9 N O3'
_chemical_formula_sum            'C13 H9 N O3'
_chemical_formula_weight         227.21
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C13H9NO3
# start Validation Reply Form
_vrf_PLAT772_s6747l              
;
PROBLEM: Suspect O-H Bond in CIF: O3H      --H3A       ..       1.45 Ang.  
RESPONSE: The formation of strong hydrogen bond between O3A-H3A...O3H 
has led to elongation of O3A-H3A bond length, leading to bridging of 
hydrogen between O3A and O3H.
;
# end Validation Reply Form
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'
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.07570(10)
_cell_length_b                   24.4204(5)
_cell_length_c                   7.3631(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.530(3)
_cell_angle_gamma                90
_cell_volume                     1016.24(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3778
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.3850
_cell_measurement_theta_min      7.2040
_shelx_estimated_absorpt_T_max   0.940
_shelx_estimated_absorpt_T_min   0.871
_exptl_absorpt_coefficient_mu    0.889
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.655
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.112a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             472
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 2 -4 0.0719
0 -1 4 0.0438
-1 15 0 0.0596
1 -15 -1 0.0797
1 -11 -3 0.0843
1 -10 3 0.0777
4 6 -3 0.0150
-3 -7 3 0.0426

_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.1275 1.5680 -4.3646 -0.3618 -0.6082 -0.7065
0.0684 -0.6703 4.4103 0.3824 0.6429 0.6637
-1.0110 15.3152 0.3347 0.3108 0.5238 -0.7931
1.0065 -15.2830 -0.7656 -0.3488 -0.5876 0.7301
0.7172 -11.1239 -3.3799 -0.5064 -0.8524 0.1302
0.6694 -9.8664 3.0993 0.0964 0.1613 0.9822
3.5464 5.8332 -2.6341 0.7774 -0.5800 -0.2435
-3.3112 -7.1057 2.8410 -0.7478 0.5579 0.3599

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5061
_diffrn_reflns_point_group_measured_fraction_full 0.788
_diffrn_reflns_point_group_measured_fraction_max 0.742
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.177
_diffrn_reflns_theta_min         6.463
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -6.00  70.00   0.50    0.17    --   43.52  10.00-150.00  152
  2  ω     79.00 128.00   0.50    0.17    --   43.52  10.00-150.00   98
  3  ω    -37.00   3.00   0.50    0.17    --   46.08  10.00   0.00   80
  4  ω     83.00 135.00   0.50    0.17    --   46.08  10.00   0.00  104
  5  ω     47.00  73.00   0.50    0.17    --   46.08  10.00   0.00   52
  6  ω     19.00  45.00   0.50    0.17    --  108.20  50.00   0.00   52
  7  ω    117.00 143.00   0.50    0.17    --  108.20   0.00 -90.00   52
  8  ω     20.00  91.00   0.50    0.17    --  108.20  60.00  60.00  142
  9  ω     24.00 113.00   0.50    0.17    --  108.20   0.00 -90.00  178
 10  ω     83.00 198.00   0.50    0.17    --  108.20  50.00   0.00  230
 11  ω     55.00  81.00   0.50    0.17    --  108.20  40.00-150.00   52
 12  ω     95.00 123.00   0.50    0.17    --  108.20  40.00-150.00   56
 13  ω    143.00 197.00   0.50    0.17    --  108.20  40.00-150.00  108
 14  ω    173.00 198.00   0.50    0.17    --  108.20   0.00   0.00   50
 15  ω    141.00 198.00   0.50    0.17    --  108.20  60.00  60.00  114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2296020000
_diffrn_orient_matrix_UB_12      0.0335219000
_diffrn_orient_matrix_UB_13      0.0882329000
_diffrn_orient_matrix_UB_21      -0.0922210000
_diffrn_orient_matrix_UB_22      0.0248123000
_diffrn_orient_matrix_UB_23      0.1509618000
_diffrn_orient_matrix_UB_31      0.1143118000
_diffrn_orient_matrix_UB_32      -0.0473347000
_diffrn_orient_matrix_UB_33      0.1415284000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_reflns_Friedel_coverage         0.522
_reflns_Friedel_fraction_full    0.572
_reflns_Friedel_fraction_max     0.522
_reflns_number_gt                3073
_reflns_number_total             3162
_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 1.171.43.112a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 44.117a 64-bit (release 07-07-2025))'
_computing_data_reduction        'CrysAlisPro 1.171.43.112a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 1020 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         3162
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0288
_refine_ls_restrained_S_all      1.063
_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)+(0.0456P)²+0.1339P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0794
_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:
 C9A(H9A), C4H(H4H), C11H(H11H), C3H(H3H), C10A(H10A), C5H(H5H), C5A(H5A),
 C11A(H11A), C10H(H10H), C1H(H1HA), C1A(H1A), C2A(H2A), C2H(H2H), C9H(H9H),
 C3A(H3AA), C4A(H4A)
;
_atom_sites_solution_hydrogens   mixed
_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
O2A O 0.5071(3) 0.40018(7) 0.6112(2) 0.0219(4) Uani 1 1 d . . . . .
O1H O 0.0995(3) 0.58633(8) 0.0897(2) 0.0229(4) Uani 1 1 d . . . . .
O3H O 0.5833(3) 0.50811(7) -0.0777(2) 0.0205(4) Uani 1 1 d . . . . .
O3A O 0.4060(3) 0.48931(7) 0.5635(2) 0.0197(4) Uani 1 1 d . . . . .
O2H O 0.4380(3) 0.59398(8) -0.1247(2) 0.0273(4) Uani 1 1 d . . . . .
O1A O 0.8703(3) 0.41279(7) 0.4254(2) 0.0199(4) Uani 1 1 d . . . . .
N1H N 0.8224(3) 0.53542(8) 0.3063(3) 0.0171(4) Uani 1 1 d . . . . .
C12H C 0.6219(4) 0.56099(10) 0.1965(3) 0.0163(4) Uani 1 1 d . . . . .
N1A N 0.1387(3) 0.45835(9) 0.1794(3) 0.0172(4) Uani 1 1 d . . . . .
C9A C 0.3890(4) 0.39435(10) 0.0058(3) 0.0181(5) Uani 1 1 d . . . . .
H9A H 0.474371 0.372826 -0.053557 0.022 Uiso 1 1 calc R U . . .
C7H C 0.2624(4) 0.61704(10) 0.1743(3) 0.0164(5) Uani 1 1 d . . . . .
C13A C 0.4272(4) 0.43961(10) 0.5058(3) 0.0159(4) Uani 1 1 d . . . . .
C8H C 0.5044(4) 0.59333(10) 0.2873(3) 0.0165(4) Uani 1 1 d . . . . .
C6A C 0.7645(4) 0.32180(10) 0.3156(3) 0.0166(5) Uani 1 1 d . . . . .
C4H C 0.3876(4) 0.76864(10) 0.2479(3) 0.0222(5) Uani 1 1 d . . . . .
H4H H 0.518600 0.792988 0.283498 0.027 Uiso 1 1 calc R U . . .
C8A C 0.4763(4) 0.40213(9) 0.2070(3) 0.0161(5) Uani 1 1 d . . . . .
C6H C 0.2303(4) 0.67693(10) 0.1853(3) 0.0171(5) Uani 1 1 d . . . . .
C11H C 0.9212(4) 0.54115(11) 0.5012(3) 0.0194(5) Uani 1 1 d . . . . .
H11H H 1.065154 0.522912 0.572564 0.023 Uiso 1 1 calc R U . . .
C13H C 0.5373(4) 0.55454(10) -0.0247(3) 0.0175(5) Uani 1 1 d . . . . .
C3H C 0.1609(4) 0.78894(11) 0.2021(3) 0.0234(5) Uani 1 1 d . . . . .
H3H H 0.136986 0.827228 0.208578 0.028 Uiso 1 1 calc R U . . .
C10A C 0.1768(4) 0.41832(10) -0.1066(3) 0.0189(5) Uani 1 1 d . . . . .
H10A H 0.112738 0.413293 -0.244089 0.023 Uiso 1 1 calc R U . . .
C5H C 0.4233(4) 0.71257(10) 0.2415(3) 0.0189(5) Uani 1 1 d . . . . .
H5H H 0.579026 0.698499 0.275517 0.023 Uiso 1 1 calc R U . . .
C5A C 0.5801(4) 0.28407(11) 0.2599(3) 0.0200(5) Uani 1 1 d . . . . .
H5A H 0.421817 0.296319 0.227504 0.024 Uiso 1 1 calc R U . . .
C11A C 0.0590(4) 0.44989(10) -0.0143(3) 0.0191(5) Uani 1 1 d . . . . .
H11A H -0.086279 0.466489 -0.092591 0.023 Uiso 1 1 calc R U . . .
C10H C 0.8129(4) 0.57357(10) 0.5974(4) 0.0193(5) Uani 1 1 d . . . . .
H10H H 0.882083 0.578288 0.734887 0.023 Uiso 1 1 calc R U . . .
C1H C 0.0024(4) 0.69764(11) 0.1367(4) 0.0206(5) Uani 1 1 d . . . . .
H1HA H -0.129559 0.673530 0.096553 0.025 Uiso 1 1 calc R U . . .
C1A C 0.9986(4) 0.30360(11) 0.3647(3) 0.0198(5) Uani 1 1 d . . . . .
H1A H 1.125930 0.328998 0.404414 0.024 Uiso 1 1 calc R U . . .
C2A C 1.0416(4) 0.24822(12) 0.3545(4) 0.0225(5) Uani 1 1 d . . . . .
H2A H 1.199469 0.235748 0.386348 0.027 Uiso 1 1 calc R U . . .
C7A C 0.7174(4) 0.38115(10) 0.3285(3) 0.0161(5) Uani 1 1 d . . . . .
C2H C -0.0318(4) 0.75367(12) 0.1469(4) 0.0235(5) Uani 1 1 d . . . . .
H2H H -0.186915 0.767828 0.116154 0.028 Uiso 1 1 calc R U . . .
C12A C 0.3422(4) 0.43399(10) 0.2871(3) 0.0155(4) Uani 1 1 d . . . . .
C9H C 0.6008(4) 0.59922(10) 0.4897(3) 0.0180(5) Uani 1 1 d . . . . .
H9H H 0.521328 0.620789 0.554032 0.022 Uiso 1 1 calc R U . . .
C3A C 0.8576(4) 0.21078(11) 0.2985(4) 0.0222(5) Uani 1 1 d . . . . .
H3AA H 0.889844 0.172912 0.292208 0.027 Uiso 1 1 calc R U . . .
C4A C 0.6261(4) 0.22847(10) 0.2514(4) 0.0226(5) Uani 1 1 d . . . . .
H4A H 0.499789 0.202796 0.213714 0.027 Uiso 1 1 calc R U . . .
H3A H 0.487(8) 0.4916(19) 0.719(7) 0.072(12) Uiso 1 1 d . . . . .
H1H H 0.902(6) 0.5133(14) 0.253(5) 0.040(8) Uiso 1 1 d . . . . .


_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
O2A C13A 1.220(3) . ?
O1H C7H 1.216(3) . ?
O3H C13H 1.263(3) . ?
O3H H3A 1.45(4) 1_554 ?
O3A C13A 1.308(3) . ?
O3A H3A 1.07(4) . ?
O2H C13H 1.228(3) . ?
O1A C7A 1.218(3) . ?
N1H C12H 1.343(3) . ?
N1H C11H 1.345(3) . ?
N1H H1H 0.90(3) . ?
C12H C8H 1.389(3) . ?
C12H C13H 1.525(3) . ?
N1A C11A 1.344(3) . ?
N1A C12A 1.339(3) . ?
C9A H9A 0.9500 . ?
C9A C8A 1.391(3) . ?
C9A C10A 1.381(3) . ?
C7H C8H 1.514(3) . ?
C7H C6H 1.482(3) . ?
C13A C12A 1.506(3) . ?
C8H C9H 1.394(3) . ?
C6A C5A 1.391(3) . ?
C6A C1A 1.405(3) . ?
C6A C7A 1.487(3) . ?
C4H H4H 0.9500 . ?
C4H C3H 1.384(4) . ?
C4H C5H 1.390(4) . ?
C8A C7A 1.499(3) . ?
C8A C12A 1.403(3) . ?
C6H C5H 1.395(3) . ?
C6H C1H 1.392(3) . ?
C11H H11H 0.9500 . ?
C11H C10H 1.380(3) . ?
C3H H3H 0.9500 . ?
C3H C2H 1.389(4) . ?
C10A H10A 0.9500 . ?
C10A C11A 1.387(3) . ?
C5H H5H 0.9500 . ?
C5A H5A 0.9500 . ?
C5A C4A 1.392(4) . ?
C11A H11A 0.9500 . ?
C10H H10H 0.9500 . ?
C10H C9H 1.390(3) . ?
C1H H1HA 0.9500 . ?
C1H C2H 1.390(4) . ?
C1A H1A 0.9500 . ?
C1A C2A 1.385(4) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.385(4) . ?
C2H H2H 0.9500 . ?
C9H H9H 0.9500 . ?
C3A H3AA 0.9500 . ?
C3A C4A 1.389(4) . ?
C4A H4A 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
C13H O3H H3A 121.1(19) . 1_554 ?
C13A O3A H3A 110(2) . . ?
C12H N1H C11H 123.0(2) . . ?
C12H N1H H1H 122(2) . . ?
C11H N1H H1H 115(2) . . ?
N1H C12H C8H 119.2(2) . . ?
N1H C12H C13H 118.0(2) . . ?
C8H C12H C13H 122.8(2) . . ?
C12A N1A C11A 117.05(19) . . ?
C8A C9A H9A 120.4 . . ?
C10A C9A H9A 120.4 . . ?
C10A C9A C8A 119.2(2) . . ?
O1H C7H C8H 119.3(2) . . ?
O1H C7H C6H 122.6(2) . . ?
C6H C7H C8H 117.9(2) . . ?
O2A C13A O3A 126.1(2) . . ?
O2A C13A C12A 120.6(2) . . ?
O3A C13A C12A 113.32(19) . . ?
C12H C8H C7H 121.3(2) . . ?
C12H C8H C9H 119.0(2) . . ?
C9H C8H C7H 119.33(19) . . ?
C5A C6A C1A 119.8(2) . . ?
C5A C6A C7A 120.7(2) . . ?
C1A C6A C7A 119.5(2) . . ?
C3H C4H H4H 120.1 . . ?
C3H C4H C5H 119.9(2) . . ?
C5H C4H H4H 120.1 . . ?
C9A C8A C7A 119.7(2) . . ?
C9A C8A C12A 118.0(2) . . ?
C12A C8A C7A 122.0(2) . . ?
C5H C6H C7H 121.3(2) . . ?
C1H C6H C7H 118.9(2) . . ?
C1H C6H C5H 119.9(2) . . ?
N1H C11H H11H 120.1 . . ?
N1H C11H C10H 119.9(2) . . ?
C10H C11H H11H 120.1 . . ?
O3H C13H C12H 113.4(2) . . ?
O2H C13H O3H 129.4(2) . . ?
O2H C13H C12H 117.3(2) . . ?
C4H C3H H3H 119.8 . . ?
C4H C3H C2H 120.4(3) . . ?
C2H C3H H3H 119.8 . . ?
C9A C10A H10A 120.7 . . ?
C9A C10A C11A 118.6(2) . . ?
C11A C10A H10A 120.7 . . ?
C4H C5H C6H 120.0(2) . . ?
C4H C5H H5H 120.0 . . ?
C6H C5H H5H 120.0 . . ?
C6A C5A H5A 119.8 . . ?
C6A C5A C4A 120.4(2) . . ?
C4A C5A H5A 119.8 . . ?
N1A C11A C10A 123.8(2) . . ?
N1A C11A H11A 118.1 . . ?
C10A C11A H11A 118.1 . . ?
C11H C10H H10H 120.6 . . ?
C11H C10H C9H 118.9(2) . . ?
C9H C10H H10H 120.6 . . ?
C6H C1H H1HA 120.1 . . ?
C2H C1H C6H 119.9(2) . . ?
C2H C1H H1HA 120.1 . . ?
C6A C1A H1A 120.4 . . ?
C2A C1A C6A 119.2(2) . . ?
C2A C1A H1A 120.4 . . ?
C1A C2A H2A 119.6 . . ?
C1A C2A C3A 120.9(2) . . ?
C3A C2A H2A 119.6 . . ?
O1A C7A C6A 122.2(2) . . ?
O1A C7A C8A 120.1(2) . . ?
C6A C7A C8A 117.7(2) . . ?
C3H C2H C1H 120.0(2) . . ?
C3H C2H H2H 120.0 . . ?
C1H C2H H2H 120.0 . . ?
N1A C12A C13A 118.19(19) . . ?
N1A C12A C8A 123.4(2) . . ?
C8A C12A C13A 118.4(2) . . ?
C8H C9H H9H 120.0 . . ?
C10H C9H C8H 120.1(2) . . ?
C10H C9H H9H 120.0 . . ?
C2A C3A H3AA 119.9 . . ?
C2A C3A C4A 120.1(3) . . ?
C4A C3A H3AA 119.9 . . ?
C5A C4A H4A 120.2 . . ?
C3A C4A C5A 119.6(2) . . ?
C3A C4A H4A 120.2 . . ?

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
O2A C13A C12A N1A 136.7(2) . . . . ?
O2A C13A C12A C8A -41.3(3) . . . . ?
O1H C7H C8H C12H 58.7(3) . . . . ?
O1H C7H C8H C9H -114.5(3) . . . . ?
O1H C7H C6H C5H -164.7(2) . . . . ?
O1H C7H C6H C1H 14.7(3) . . . . ?
O3A C13A C12A N1A -43.5(3) . . . . ?
O3A C13A C12A C8A 138.4(2) . . . . ?
N1H C12H C8H C7H -172.0(2) . . . . ?
N1H C12H C8H C9H 1.3(3) . . . . ?
N1H C12H C13H O3H 33.9(3) . . . . ?
N1H C12H C13H O2H -145.6(2) . . . . ?
N1H C11H C10H C9H 0.8(4) . . . . ?
C12H N1H C11H C10H 1.4(4) . . . . ?
C12H C8H C9H C10H 0.9(4) . . . . ?
C9A C8A C7A O1A 119.8(3) . . . . ?
C9A C8A C7A C6A -56.5(3) . . . . ?
C9A C8A C12A N1A -1.8(3) . . . . ?
C9A C8A C12A C13A 176.1(2) . . . . ?
C9A C10A C11A N1A -0.5(4) . . . . ?
C7H C8H C9H C10H 174.3(2) . . . . ?
C7H C6H C5H C4H 179.1(2) . . . . ?
C7H C6H C1H C2H 179.7(2) . . . . ?
C8H C12H C13H O3H -148.1(2) . . . . ?
C8H C12H C13H O2H 32.3(3) . . . . ?
C8H C7H C6H C5H 20.3(3) . . . . ?
C8H C7H C6H C1H -160.2(2) . . . . ?
C6A C5A C4A C3A -0.2(4) . . . . ?
C6A C1A C2A C3A -0.6(4) . . . . ?
C4H C3H C2H C1H -0.2(4) . . . . ?
C8A C9A C10A C11A 0.6(4) . . . . ?
C6H C7H C8H C12H -126.1(2) . . . . ?
C6H C7H C8H C9H 60.7(3) . . . . ?
C6H C1H C2H C3H 1.2(4) . . . . ?
C11H N1H C12H C8H -2.5(3) . . . . ?
C11H N1H C12H C13H 175.6(2) . . . . ?
C11H C10H C9H C8H -1.9(4) . . . . ?
C13H C12H C8H C7H 10.1(4) . . . . ?
C13H C12H C8H C9H -176.7(2) . . . . ?
C3H C4H C5H C6H 1.3(4) . . . . ?
C10A C9A C8A C7A -173.9(2) . . . . ?
C10A C9A C8A C12A 0.4(3) . . . . ?
C5H C4H C3H C2H -1.0(4) . . . . ?
C5H C6H C1H C2H -0.9(4) . . . . ?
C5A C6A C1A C2A 0.8(4) . . . . ?
C5A C6A C7A O1A 159.1(2) . . . . ?
C5A C6A C7A C8A -24.7(3) . . . . ?
C11A N1A C12A C13A -175.9(2) . . . . ?
C11A N1A C12A C8A 2.0(3) . . . . ?
C1H C6H C5H C4H -0.4(4) . . . . ?
C1A C6A C5A C4A -0.4(4) . . . . ?
C1A C6A C7A O1A -19.4(3) . . . . ?
C1A C6A C7A C8A 156.8(2) . . . . ?
C1A C2A C3A C4A 0.0(4) . . . . ?
C2A C3A C4A C5A 0.4(4) . . . . ?
C7A C6A C5A C4A -178.9(2) . . . . ?
C7A C6A C1A C2A 179.3(2) . . . . ?
C7A C8A C12A N1A 172.4(2) . . . . ?
C7A C8A C12A C13A -9.7(3) . . . . ?
C12A N1A C11A C10A -0.8(4) . . . . ?
C12A C8A C7A O1A -54.4(3) . . . . ?
C12A C8A C7A C6A 129.3(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 1.406
_oxdiff_exptl_absorpt_empirical_full_min 0.815
####################################################################### 
# 
# 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_s6737r
_database_code_depnum_ccdc_archive 'CCDC 2475756'
loop_
_audit_author_name
_audit_author_address
'Avantika Hasija'
;University of Manchester
United Kingdom
;
_audit_update_record             
;
2025-07-24 deposited with the CCDC.	2026-06-08 downloaded from the CCDC.
;
_audit_creation_date             2025-07-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7308)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H7 Cl F3 N O'
_chemical_formula_sum            'C13 H7 Cl F3 N O'
_chemical_formula_weight         285.65
_chemical_melting_point          ?
_chemical_oxdiff_formula         C13H7ClF3NO
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/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                   9.6528(4)
_cell_length_b                   7.5835(3)
_cell_length_c                   16.5958(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.477(4)
_cell_angle_gamma                90
_cell_volume                     1170.80(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3603
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      77.3570
_cell_measurement_theta_min      4.7440
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.206
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.740
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.112a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-6 0 0 0.0193
6 0 -1 0.0070
1 -3 -8 0.0867
0 3 8 0.0612
2 1 -10 0.0478
-2 -1 11 0.0297
-1 -5 2 0.0539
0 5 1 0.0588

_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_min          0.028
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-6.0599 0.3269 0.2632 0.5665 -0.8200 -0.0815
6.0885 -0.4299 -0.5470 -0.5648 0.8172 0.1150
1.1321 -3.0700 -8.4316 0.0251 -0.0452 0.9987
-0.4533 3.0248 8.3781 -0.0882 0.1365 -0.9867
2.3778 1.0286 -10.4484 0.5857 0.5066 0.6328
-2.3731 -0.7924 10.5521 -0.5613 -0.4859 -0.6699
-0.9704 -4.8109 1.9377 -0.6747 -0.5755 0.4622
0.3751 4.8914 0.8570 0.5616 0.4771 -0.6761

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6793
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.377
_diffrn_reflns_theta_min         4.754
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -2.00  46.00   0.50    0.05    --   46.62 -69.00 -32.00   96
  2  ω     35.00  60.00   0.50    0.08    --  107.75 -61.00-120.00   50
  3  ω     41.00  82.00   0.50    0.08    --  107.75 -69.00 -32.00   82
  4  ω     36.00  62.00   0.50    0.08    --  107.75 -61.00  30.00   52
  5  ω     45.00  70.00   0.50    0.08    --  107.75 -61.00  90.00   50
  6  ω     39.00  67.00   0.50    0.08    --  107.75 -61.00 120.00   56
  7  ω     99.00 170.00   0.50    0.08    --  107.75  45.00  30.00  142
  8  ω    142.00 173.00   0.50    0.08    --  107.75  45.00   0.00   62
  9  ω    106.00 134.00   0.50    0.08    --  107.75  45.00   0.00   56
 10  ω    106.00 175.00   0.50    0.08    --  107.75  69.00  99.00  138
 11  ω     48.00  73.00   0.50    0.05    --   46.62  69.00  99.00   50
 12  ω     -7.00  28.00   0.50    0.05    --  -46.62  19.00  90.00   70
 13  ω    -21.00  17.00   0.50    0.05    --  -46.62  69.00  99.00   76
 14  ω    -52.00 -26.00   0.50    0.05    --  -46.62  69.00  99.00   52
 15  ω     36.00  99.00   0.50    0.08    --  107.75 -95.00-120.00  126
 16  ω    -21.00  21.00   0.50    0.05    --  -46.62  19.00 -90.00   84
 17  ω    -22.00   4.00   0.50    0.05    --  -46.62  19.00-120.00   52
 18  ω    -70.00 -45.00   0.50    0.08    -- -109.00  61.00 -30.00   50
 19  ω    -67.00 -42.00   0.50    0.08    -- -109.00  61.00 -60.00   50
 20  ω    -78.00 -39.00   0.50    0.08    -- -109.00  69.00  99.00   78
 21  ω    -66.00 -41.00   0.50    0.08    -- -109.00  61.00  60.00   50
 22  ω   -164.00-139.00   0.50    0.08    -- -109.00 -45.00 -90.00   50
 23  ω   -173.00-133.00   0.50    0.08    -- -109.00 -69.00 -32.00   80
 24  ω   -121.00 -96.00   0.50    0.08    -- -109.00 -45.00 -90.00   50
 25  ω   -118.00 -28.00   0.50    0.05    --  -46.62 -69.00 -32.00  180
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0890788000
_diffrn_orient_matrix_UB_12      0.1327210000
_diffrn_orient_matrix_UB_13      -0.0632603000
_diffrn_orient_matrix_UB_21      0.1397261000
_diffrn_orient_matrix_UB_22      0.0882182000
_diffrn_orient_matrix_UB_23      -0.0079995000
_diffrn_orient_matrix_UB_31      0.0035269000
_diffrn_orient_matrix_UB_32      -0.1258463000
_diffrn_orient_matrix_UB_33      -0.0721474000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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                1919
_reflns_number_total             2353
_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 1.171.43.112a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 44.117a 64-bit (release 07-07-2025))'
_computing_data_reduction        'CrysAlisPro 1.171.43.112a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0390
_refine_ls_restrained_S_all      1.057
_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)+(0.0339P)²+0.7786P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.0972
_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:
 C9(H9), C1(H1), C3(H3), C13(H13), C10(H10), 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 0.77268(6) 0.44333(7) 0.56172(3) 0.02546(15) Uani 1 1 d . . . . .
F1 F 0.22126(14) 0.08672(18) 0.67115(7) 0.0272(3) Uani 1 1 d . . . . .
F3 F 0.21879(15) -0.04339(18) 0.55564(8) 0.0320(3) Uani 1 1 d . . . . .
F2 F 0.11710(14) 0.20883(19) 0.55346(8) 0.0336(3) Uani 1 1 d . . . . .
O1 O 0.49960(17) 0.2773(2) 0.80405(9) 0.0303(4) Uani 1 1 d . . . . .
N1 N 0.40867(19) 0.1765(2) 0.52120(10) 0.0209(4) Uani 1 1 d . . . . .
C8 C 0.2907(2) 0.4452(3) 0.74472(12) 0.0180(4) Uani 1 1 d . . . . .
C4 C 0.4516(2) 0.3060(3) 0.65839(12) 0.0183(4) Uani 1 1 d . . . . .
C9 C 0.2500(2) 0.4492(3) 0.81966(12) 0.0200(4) Uani 1 1 d . . . . .
H9 H 0.301087 0.380960 0.866125 0.024 Uiso 1 1 calc R U . . .
C5 C 0.3711(2) 0.2048(3) 0.59228(12) 0.0186(4) Uani 1 1 d . . . . .
C7 C 0.4171(2) 0.3379(3) 0.74159(12) 0.0206(4) Uani 1 1 d . . . . .
C1 C 0.5291(2) 0.2509(3) 0.51297(12) 0.0208(4) Uani 1 1 d . . . . .
H1 H 0.555680 0.234481 0.462342 0.025 Uiso 1 1 calc R U . . .
C3 C 0.5793(2) 0.3792(3) 0.64990(12) 0.0199(4) Uani 1 1 d . . . . .
H3 H 0.639316 0.446544 0.693836 0.024 Uiso 1 1 calc R U . . .
C2 C 0.6167(2) 0.3516(3) 0.57588(12) 0.0206(4) Uani 1 1 d . . . . .
C13 C 0.2150(2) 0.5461(3) 0.67680(12) 0.0202(4) Uani 1 1 d . . . . .
H13 H 0.241849 0.543404 0.625751 0.024 Uiso 1 1 calc R U . . .
C10 C 0.1352(2) 0.5526(3) 0.82590(13) 0.0226(4) Uani 1 1 d . . . . .
H10 H 0.106960 0.554336 0.876514 0.027 Uiso 1 1 calc R U . . .
C11 C 0.0612(2) 0.6540(3) 0.75838(13) 0.0238(5) Uani 1 1 d . . . . .
H11 H -0.016682 0.726007 0.763195 0.029 Uiso 1 1 calc R U . . .
C12 C 0.1008(2) 0.6503(3) 0.68380(13) 0.0236(5) Uani 1 1 d . . . . .
H12 H 0.049625 0.719187 0.637621 0.028 Uiso 1 1 calc R U . . .
C6 C 0.2322(2) 0.1139(3) 0.59289(13) 0.0225(5) Uani 1 1 d . . . . .


_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 C2 1.731(2) . ?
F1 C6 1.347(2) . ?
F3 C6 1.334(3) . ?
F2 C6 1.339(3) . ?
O1 C7 1.216(3) . ?
N1 C5 1.341(2) . ?
N1 C1 1.332(3) . ?
C8 C9 1.401(3) . ?
C8 C7 1.480(3) . ?
C8 C13 1.397(3) . ?
C4 C5 1.393(3) . ?
C4 C7 1.523(3) . ?
C4 C3 1.393(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.384(3) . ?
C5 C6 1.510(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.385(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.386(3) . ?
C13 H13 0.9500 . ?
C13 C12 1.386(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.389(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.390(3) . ?
C12 H12 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
C1 N1 C5 118.08(18) . . ?
C9 C8 C7 118.20(18) . . ?
C13 C8 C9 119.63(19) . . ?
C13 C8 C7 122.12(17) . . ?
C5 C4 C7 126.17(19) . . ?
C3 C4 C5 117.55(17) . . ?
C3 C4 C7 116.21(18) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.90(19) . . ?
C10 C9 H9 120.1 . . ?
N1 C5 C4 123.79(19) . . ?
N1 C5 C6 112.44(18) . . ?
C4 C5 C6 123.76(17) . . ?
O1 C7 C8 122.44(18) . . ?
O1 C7 C4 117.45(19) . . ?
C8 C7 C4 120.06(17) . . ?
N1 C1 H1 119.0 . . ?
N1 C1 C2 122.05(18) . . ?
C2 C1 H1 119.0 . . ?
C4 C3 H3 120.8 . . ?
C2 C3 C4 118.45(19) . . ?
C2 C3 H3 120.8 . . ?
C1 C2 Cl1 119.85(15) . . ?
C1 C2 C3 120.0(2) . . ?
C3 C2 Cl1 120.11(17) . . ?
C8 C13 H13 120.0 . . ?
C12 C13 C8 120.07(18) . . ?
C12 C13 H13 120.0 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.20(19) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.2(2) . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 120.0(2) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
F1 C6 C5 111.99(17) . . ?
F3 C6 F1 106.70(17) . . ?
F3 C6 F2 106.81(17) . . ?
F3 C6 C5 112.43(17) . . ?
F2 C6 F1 106.58(17) . . ?
F2 C6 C5 111.95(18) . . ?

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
N1 C5 C6 F1 157.25(18) . . . . ?
N1 C5 C6 F3 37.1(2) . . . . ?
N1 C5 C6 F2 -83.1(2) . . . . ?
N1 C1 C2 Cl1 179.43(16) . . . . ?
N1 C1 C2 C3 -0.8(3) . . . . ?
C8 C9 C10 C11 -0.7(3) . . . . ?
C8 C13 C12 C11 -0.2(3) . . . . ?
C4 C5 C6 F1 -22.5(3) . . . . ?
C4 C5 C6 F3 -142.6(2) . . . . ?
C4 C5 C6 F2 97.2(2) . . . . ?
C4 C3 C2 Cl1 178.82(16) . . . . ?
C4 C3 C2 C1 -1.0(3) . . . . ?
C9 C8 C7 O1 -12.1(3) . . . . ?
C9 C8 C7 C4 170.42(19) . . . . ?
C9 C8 C13 C12 0.3(3) . . . . ?
C9 C10 C11 C12 0.8(3) . . . . ?
C5 N1 C1 C2 1.6(3) . . . . ?
C5 C4 C7 O1 114.0(2) . . . . ?
C5 C4 C7 C8 -68.4(3) . . . . ?
C5 C4 C3 C2 1.8(3) . . . . ?
C7 C8 C9 C10 177.84(19) . . . . ?
C7 C8 C13 C12 -177.3(2) . . . . ?
C7 C4 C5 N1 -177.9(2) . . . . ?
C7 C4 C5 C6 1.8(3) . . . . ?
C7 C4 C3 C2 178.97(18) . . . . ?
C1 N1 C5 C4 -0.7(3) . . . . ?
C1 N1 C5 C6 179.56(18) . . . . ?
C3 C4 C5 N1 -1.0(3) . . . . ?
C3 C4 C5 C6 178.7(2) . . . . ?
C3 C4 C7 O1 -62.9(3) . . . . ?
C3 C4 C7 C8 114.7(2) . . . . ?
C13 C8 C9 C10 0.1(3) . . . . ?
C13 C8 C7 O1 165.5(2) . . . . ?
C13 C8 C7 C4 -11.9(3) . . . . ?
C10 C11 C12 C13 -0.4(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 1.189
_oxdiff_exptl_absorpt_empirical_full_min 0.815
####################################################################### 
# 
# 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_s6748r
_database_code_depnum_ccdc_archive 'CCDC 2487303'
loop_
_audit_author_name
_audit_author_address
' Avantika Hasija'
;The University of Manchester
United Kingdom
;
_audit_update_record             
;
2025-09-11 deposited with the CCDC.	2026-06-08 downloaded from the CCDC.
;
_audit_creation_date             2025-09-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H12 F3 N O'
_chemical_formula_sum            'C19 H12 F3 N O'
_chemical_formula_weight         327.30
_chemical_absolute_configuration unk
_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           41
_space_group_name_H-M_alt        'A e a 2'
_space_group_name_Hall           'A 2 -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, z+1/2'

_cell_length_a                   31.5336(3)
_cell_length_b                   35.2182(4)
_cell_length_c                   8.08290(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     8976.52(17)
_cell_formula_units_Z            24
_cell_measurement_reflns_used    29778
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      77.4330
_cell_measurement_theta_min      2.5320
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.986
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82233
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.44.117a (Rigaku Oxford Diffraction, 2025)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             4032
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            54418
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.821
_diffrn_reflns_theta_min         2.509
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_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    -56.00  26.00   0.50    0.10    --  -46.87  57.00  54.00  164
  2  ω    -22.00  21.00   0.50    0.10    --  -46.87  19.00-150.00   86
  3  ω    -39.00 -12.00   0.50    0.10    --  -46.87  38.00-180.00   54
  4  ω     66.00 100.00   0.50    0.10    --  107.75 -95.00   0.00   68
  5  ω     35.00  60.00   0.50    0.10    --  107.75 -95.00   0.00   50
  6  ω     38.00  64.00   0.50    0.10    --  107.75 -61.00  60.00   52
  7  ω     36.00  66.00   0.50    0.10    --  107.75 -61.00 120.00   60
  8  ω     36.00  70.00   0.50    0.10    --  107.75 -61.00 150.00   68
  9  ω     48.00  73.00   0.50    0.10    --  107.75 -61.00  90.00   50
 10  ω     47.00  73.00   0.50    0.10    --  107.75 -61.00 -30.00   52
 11  ω     35.00  67.00   0.50    0.10    --  107.75 -57.00 -86.00   64
 12  ω     14.00  40.00   0.50    0.10    --   46.87 -57.00 -86.00   52
 13  ω    104.00 156.00   0.50    0.10    --  107.75  15.00 -30.00  104
 14  ω    135.00 172.00   0.50    0.10    --  107.75  61.00 -30.00   74
 15  ω     92.00 119.00   0.50    0.10    --  107.75  61.00 -30.00   54
 16  ω     85.00 116.00   0.50    0.10    --  107.75  77.00 120.00   62
 17  ω     92.00 118.00   0.50    0.10    --  107.75  61.00 150.00   52
 18  ω    127.00 172.00   0.50    0.10    --  107.75  77.00 120.00   90
 19  ω     93.00 144.00   0.50    0.10    --  107.75  57.00  54.00  102
 20  ω     95.00 126.00   0.50    0.10    --  107.75  45.00-180.00   62
 21  ω    116.00 170.00   0.50    0.10    --  107.75  45.00-120.00  108
 22  ω     56.00  82.00   0.50    0.10    --   46.87  57.00  54.00   52
 23  ω     35.00 118.00   0.50    0.10    --   46.87  38.00 150.00  166
 24  ω    -71.00 -36.00   0.50    0.10    -- -109.00  61.00 -90.00   70
 25  ω    -65.00 -36.00   0.50    0.10    -- -109.00  57.00  54.00   58
 26  ω    -66.00 -40.00   0.50    0.10    -- -109.00  61.00  90.00   52
 27  ω    -69.00 -41.00   0.50    0.10    -- -109.00  61.00 120.00   56
 28  ω     35.00  92.00   0.50    0.10    --   46.87  57.00-180.00  114
 29  ω   -111.00 -86.00   0.50    0.10    -- -109.00 -77.00-180.00   50
 30  ω   -118.00 -92.00   0.50    0.10    -- -109.00 -61.00-150.00   52
 31  ω   -152.00 -92.00   0.50    0.10    -- -109.00 -61.00-120.00  120
 32  ω   -122.00 -95.00   0.50    0.10    -- -109.00 -57.00 -86.00   54
 33  ω   -119.00 -32.00   0.50    0.10    --  -46.87 -57.00 -86.00  174
 34  ω   -123.00 -98.00   0.50    0.10    -- -109.00 -49.00-155.73   50
 35  ω   -118.00 -93.00   0.50    0.10    -- -109.00 -60.00 155.30   50
 36  ω   -118.00 -93.00   0.50    0.10    -- -109.00 -59.00 165.43   50
 37  ω   -174.00-108.00   0.50    0.10    -- -109.00 -49.00 134.41  132
 38  ω   -147.00-100.00   0.50    0.10    -- -109.00 -56.00 146.28   94
 39  ω   -119.00 -94.00   0.50    0.10    -- -109.00 -55.00 178.32   50
 40  ω   -120.00 -95.00   0.50    0.10    -- -109.00 -48.00 156.55   50
 41  ω   -162.00-104.00   0.50    0.10    -- -109.00 -15.00   0.00  116
 42  ω   -163.00-138.00   0.50    0.10    -- -109.00 -15.00 120.00   50
 43  ω   -167.00-104.00   0.50    0.10    -- -109.00 -45.00 -30.00  126
 44  ω   -132.00 -97.00   0.50    0.10    -- -109.00 -45.00-180.00   70
 45  ω   -164.00-139.00   0.50    0.10    -- -109.00 -45.00-180.00   50
 46  ω   -170.00-102.00   0.50    0.10    -- -109.00 -15.00-180.00  136
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, SynergyCustom DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1254687000
_diffrn_orient_matrix_UB_12      -0.0326361000
_diffrn_orient_matrix_UB_13      -0.0048856000
_diffrn_orient_matrix_UB_21      -0.0348991000
_diffrn_orient_matrix_UB_22      -0.0125758000
_diffrn_orient_matrix_UB_23      0.0459416000
_diffrn_orient_matrix_UB_31      -0.1391357000
_diffrn_orient_matrix_UB_32      -0.0262527000
_diffrn_orient_matrix_UB_33      -0.0159378000
_diffrn_oxdiff_digest_hkl        
;
43df8feb2d19f6d5337d93e88b437f43d7c92c
;
_diffrn_oxdiff_digest_od_ed      
;

;
_diffrn_oxdiff_measurement_exp_name s6748r.par
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.831
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.958
_reflns_number_gt                8633
_reflns_number_total             9357
_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 1.171.44.117a (Rigaku OD, 2025)'
_computing_data_collection       'CrysAlisPro 1.171.44.117a (Rigaku OD, 2025)'
_computing_data_reduction        'CrysAlisPro 1.171.44.117a (Rigaku OD, 2025)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 3624 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     649
_refine_ls_number_reflns         9357
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0324
_refine_ls_restrained_S_all      1.037
_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)+(0.0362P)²+2.7643P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0772
_refine_ls_wR_factor_ref         0.0790
_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:
 C5C(H5C), C11C(H11C), C5B(H5B), C9A(H9A), C12C(H12C), C8A(H8A), C1B(H1B),
 C8B(H8B), C9B(H9B), C1C(H1C), C4B(H4B), C3B(H3B), C11B(H11B), C4C(H4C),
 C4A(H4A), C17A(H17A), C12A(H12A), C16B(H16B), C15B(H15B), C12B(H12B), C1A(H1A),
  C15A(H15A), C3A(H3A), C3C(H3C), C2B(H2B), C2A(H2A), C16A(H16A), C9C(H9C),
 C17B(H17B), C8C(H8C), C11A(H11A), C2C(H2C), C5A(H5A), C15C(H15C), C17C(H17C),
 C16C(H16C)
;
_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
F1A F 0.34341(4) 0.25074(4) -0.16691(18) 0.0327(3) Uani 1 1 d . . . . .
F3A F 0.27611(4) 0.24274(4) -0.15431(19) 0.0354(3) Uani 1 1 d . . . . .
F1B F 0.32645(5) 0.56142(4) 0.18051(18) 0.0374(4) Uani 1 1 d . . . . .
F3C F 0.49768(5) 0.53875(5) 0.8322(2) 0.0417(4) Uani 1 1 d . . . . .
F2A F 0.31641(6) 0.19628(5) -0.22387(18) 0.0417(4) Uani 1 1 d . . . . .
F2C F 0.48991(6) 0.59779(4) 0.78005(19) 0.0406(4) Uani 1 1 d . . . . .
F1C F 0.43590(5) 0.56320(5) 0.8374(2) 0.0406(4) Uani 1 1 d . . . . .
O1A O 0.41683(5) 0.23037(5) 0.0541(2) 0.0306(4) Uani 1 1 d . . . . .
F2B F 0.31570(7) 0.62051(5) 0.1407(2) 0.0548(5) Uani 1 1 d . . . . .
O1C O 0.56810(5) 0.56794(5) 0.5412(2) 0.0331(4) Uani 1 1 d . . . . .
F3B F 0.37867(7) 0.59786(6) 0.1236(2) 0.0593(5) Uani 1 1 d . . . . .
O1B O 0.25398(6) 0.57823(5) 0.4078(3) 0.0364(4) Uani 1 1 d . . . . .
N1A N 0.28470(6) 0.19028(6) 0.0995(3) 0.0255(4) Uani 1 1 d . . . . .
N1C N 0.43349(6) 0.53326(6) 0.5392(3) 0.0294(5) Uani 1 1 d . . . . .
N1B N 0.38161(7) 0.62674(6) 0.4239(3) 0.0290(4) Uani 1 1 d . . . . .
C6B C 0.29220(7) 0.40056(7) 0.5665(3) 0.0227(4) Uani 1 1 d . . . . .
C5C C 0.56809(7) 0.76892(7) 0.6272(3) 0.0257(5) Uani 1 1 d . . . . .
H5C H 0.581319 0.754233 0.711223 0.031 Uiso 1 1 calc R U . . .
C11C C 0.50445(7) 0.65075(7) 0.4412(3) 0.0233(5) Uani 1 1 d . . . . .
H11C H 0.479057 0.638563 0.406835 0.028 Uiso 1 1 calc R U . . .
C10A C 0.38637(7) 0.29041(7) 0.1141(3) 0.0238(5) Uani 1 1 d . . . . .
C10C C 0.53938(7) 0.62902(7) 0.4889(3) 0.0234(5) Uani 1 1 d . . . . .
C7A C 0.38516(7) 0.36995(6) 0.0946(3) 0.0242(5) Uani 1 1 d . . . . .
C19A C 0.31328(7) 0.22580(7) -0.1222(3) 0.0260(5) Uani 1 1 d . . . . .
C5B C 0.31866(7) 0.38368(7) 0.6845(3) 0.0241(5) Uani 1 1 d . . . . .
H5B H 0.335549 0.399301 0.754138 0.029 Uiso 1 1 calc R U . . .
C9A C 0.42276(7) 0.31019(7) 0.0673(3) 0.0283(5) Uani 1 1 d . . . . .
H9A H 0.447988 0.296677 0.041659 0.034 Uiso 1 1 calc R U . . .
C12C C 0.50668(7) 0.69006(7) 0.4436(3) 0.0226(4) Uani 1 1 d . . . . .
H12C H 0.482715 0.704614 0.411282 0.027 Uiso 1 1 calc R U . . .
C19C C 0.47245(8) 0.56355(7) 0.7551(3) 0.0261(5) Uani 1 1 d . . . . .
C14A C 0.34781(7) 0.22649(6) 0.1621(3) 0.0230(5) Uani 1 1 d . . . . .
C6C C 0.54616(7) 0.75061(7) 0.4995(3) 0.0222(4) Uani 1 1 d . . . . .
C8A C 0.42225(7) 0.34941(7) 0.0582(3) 0.0277(5) Uani 1 1 d . . . . .
H8A H 0.447259 0.362635 0.026956 0.033 Uiso 1 1 calc R U . . .
C7B C 0.29019(7) 0.44245(7) 0.5476(3) 0.0227(5) Uani 1 1 d . . . . .
C1B C 0.26801(7) 0.37663(7) 0.4664(3) 0.0278(5) Uani 1 1 d . . . . .
H1B H 0.249906 0.387387 0.384948 0.033 Uiso 1 1 calc R U . . .
C6A C 0.38297(7) 0.41167(7) 0.0704(3) 0.0242(5) Uani 1 1 d . . . . .
C14C C 0.49691(7) 0.56650(7) 0.4568(3) 0.0247(5) Uani 1 1 d . . . . .
C8B C 0.32529(7) 0.46536(7) 0.5842(3) 0.0236(5) Uani 1 1 d . . . . .
H8B H 0.350675 0.453921 0.623169 0.028 Uiso 1 1 calc R U . . .
C7C C 0.54381(7) 0.70850(7) 0.4932(3) 0.0220(4) Uani 1 1 d . . . . .
C9B C 0.32359(7) 0.50425(7) 0.5645(3) 0.0238(5) Uani 1 1 d . . . . .
H9B H 0.347625 0.519268 0.591721 0.029 Uiso 1 1 calc R U . . .
C14B C 0.32313(7) 0.58708(7) 0.5117(3) 0.0248(5) Uani 1 1 d . . . . .
C18C C 0.46738(7) 0.55455(6) 0.5741(3) 0.0242(5) Uani 1 1 d . . . . .
C13A C 0.38643(7) 0.24826(7) 0.1057(3) 0.0238(5) Uani 1 1 d . . . . .
C13C C 0.53773(7) 0.58703(7) 0.4997(3) 0.0245(5) Uani 1 1 d . . . . .
C1C C 0.52683(7) 0.77292(7) 0.3781(3) 0.0242(5) Uani 1 1 d . . . . .
H1C H 0.511561 0.761069 0.290942 0.029 Uiso 1 1 calc R U . . .
C18A C 0.31615(7) 0.21387(6) 0.0563(3) 0.0219(4) Uani 1 1 d . . . . .
C10B C 0.28679(7) 0.52182(7) 0.5048(3) 0.0243(5) Uani 1 1 d . . . . .
C4B C 0.32062(7) 0.34455(7) 0.7015(3) 0.0259(5) Uani 1 1 d . . . . .
H4B H 0.338609 0.333626 0.782929 0.031 Uiso 1 1 calc R U . . .
C3B C 0.29640(8) 0.32122(7) 0.6001(3) 0.0287(5) Uani 1 1 d . . . . .
H3B H 0.298013 0.294394 0.610567 0.034 Uiso 1 1 calc R U . . .
C11B C 0.25155(8) 0.49918(7) 0.4690(3) 0.0279(5) Uani 1 1 d . . . . .
H11B H 0.226248 0.510662 0.429482 0.033 Uiso 1 1 calc R U . . .
C4C C 0.57078(8) 0.80819(7) 0.6328(3) 0.0277(5) Uani 1 1 d . . . . .
H4C H 0.585728 0.820212 0.720356 0.033 Uiso 1 1 calc R U . . .
C4A C 0.40130(8) 0.46750(7) -0.0901(3) 0.0279(5) Uani 1 1 d . . . . .
H4A H 0.416978 0.478899 -0.177322 0.033 Uiso 1 1 calc R U . . .
C17A C 0.28346(8) 0.17914(7) 0.2571(3) 0.0274(5) Uani 1 1 d . . . . .
H17A H 0.262009 0.161773 0.289973 0.033 Uiso 1 1 calc R U . . .
C18B C 0.34915(8) 0.60344(7) 0.3914(3) 0.0255(5) Uani 1 1 d . . . . .
C12A C 0.34947(7) 0.34981(7) 0.1473(3) 0.0263(5) Uani 1 1 d . . . . .
H12A H 0.324469 0.363266 0.176686 0.032 Uiso 1 1 calc R U . . .
C16B C 0.36594(8) 0.61926(7) 0.7115(3) 0.0282(5) Uani 1 1 d . . . . .
H16B H 0.372775 0.625199 0.823019 0.034 Uiso 1 1 calc R U . . .
C15B C 0.33269(8) 0.59508(7) 0.6759(3) 0.0271(5) Uani 1 1 d . . . . .
H15B H 0.316523 0.584044 0.762642 0.033 Uiso 1 1 calc R U . . .
C13B C 0.28494(7) 0.56316(7) 0.4699(3) 0.0274(5) Uani 1 1 d . . . . .
C12B C 0.25313(7) 0.46038(7) 0.4905(3) 0.0271(5) Uani 1 1 d . . . . .
H12B H 0.228771 0.445503 0.466386 0.032 Uiso 1 1 calc R U . . .
C1A C 0.35641(8) 0.43423(7) 0.1668(3) 0.0269(5) Uani 1 1 d . . . . .
H1A H 0.341321 0.423137 0.256359 0.032 Uiso 1 1 calc R U . . .
C15A C 0.34491(8) 0.21536(7) 0.3273(3) 0.0273(5) Uani 1 1 d . . . . .
H15A H 0.365193 0.223872 0.405907 0.033 Uiso 1 1 calc R U . . .
C3A C 0.37380(7) 0.48927(7) 0.0050(3) 0.0275(5) Uani 1 1 d . . . . .
H3A H 0.370196 0.515505 -0.018433 0.033 Uiso 1 1 calc R U . . .
C3C C 0.55173(8) 0.82993(7) 0.5110(3) 0.0289(5) Uani 1 1 d . . . . .
H3C H 0.553701 0.856838 0.514476 0.035 Uiso 1 1 calc R U . . .
C2B C 0.26982(8) 0.33757(7) 0.4832(3) 0.0304(5) Uani 1 1 d . . . . .
H2B H 0.252804 0.321877 0.414416 0.036 Uiso 1 1 calc R U . . .
C2A C 0.35166(8) 0.47262(7) 0.1340(3) 0.0286(5) Uani 1 1 d . . . . .
H2A H 0.333174 0.487561 0.200208 0.034 Uiso 1 1 calc R U . . .
C16A C 0.31209(8) 0.19176(7) 0.3750(3) 0.0293(5) Uani 1 1 d . . . . .
H16A H 0.309178 0.184284 0.487397 0.035 Uiso 1 1 calc R U . . .
C9C C 0.57693(7) 0.64737(7) 0.5343(3) 0.0278(5) Uani 1 1 d . . . . .
H9C H 0.601179 0.632831 0.563375 0.033 Uiso 1 1 calc R U . . .
C17B C 0.38914(8) 0.63469(7) 0.5831(3) 0.0280(5) Uani 1 1 d . . . . .
H17B H 0.411505 0.651764 0.609004 0.034 Uiso 1 1 calc R U . . .
C8C C 0.57892(7) 0.68633(7) 0.5369(3) 0.0267(5) Uani 1 1 d . . . . .
H8C H 0.604561 0.698440 0.568924 0.032 Uiso 1 1 calc R U . . .
C11A C 0.34993(7) 0.31061(7) 0.1574(3) 0.0252(5) Uani 1 1 d . . . . .
H11A H 0.325390 0.297399 0.193948 0.030 Uiso 1 1 calc R U . . .
C19B C 0.34266(9) 0.59594(7) 0.2091(3) 0.0333(6) Uani 1 1 d . . . . .
C2C C 0.52970(8) 0.81222(7) 0.3836(3) 0.0282(5) Uani 1 1 d . . . . .
H2C H 0.516558 0.827070 0.299954 0.034 Uiso 1 1 calc R U . . .
C5A C 0.40577(8) 0.42907(7) -0.0573(3) 0.0270(5) Uani 1 1 d . . . . .
H5A H 0.424629 0.414301 -0.122529 0.032 Uiso 1 1 calc R U . . .
C15C C 0.48971(9) 0.55598(8) 0.2932(3) 0.0334(6) Uani 1 1 d . . . . .
H15C H 0.508591 0.563889 0.208307 0.040 Uiso 1 1 calc R U . . .
C17C C 0.42796(8) 0.52312(8) 0.3816(4) 0.0356(6) Uani 1 1 d . . . . .
H17C H 0.404282 0.507625 0.354718 0.043 Uiso 1 1 calc R U . . .
C16C C 0.45493(9) 0.53401(8) 0.2557(4) 0.0377(6) Uani 1 1 d . . . . .
H16C H 0.449556 0.526445 0.144901 0.045 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
F1A C19A 1.343(3) . ?
F3A C19A 1.340(3) . ?
F1B C19B 1.339(3) . ?
F3C C19C 1.336(3) . ?
F2A C19A 1.329(3) . ?
F2C C19C 1.341(3) . ?
F1C C19C 1.331(3) . ?
O1A C13A 1.221(3) . ?
F2B C19B 1.333(3) . ?
O1C C13C 1.217(3) . ?
F3B C19B 1.331(3) . ?
O1B C13B 1.219(3) . ?
N1A C18A 1.340(3) . ?
N1A C17A 1.334(3) . ?
N1C C18C 1.335(3) . ?
N1C C17C 1.334(4) . ?
N1B C18B 1.338(3) . ?
N1B C17B 1.338(3) . ?
C6B C5B 1.400(3) . ?
C6B C7B 1.485(3) . ?
C6B C1B 1.395(3) . ?
C5C H5C 0.9500 . ?
C5C C6C 1.400(3) . ?
C5C C4C 1.387(4) . ?
C11C H11C 0.9500 . ?
C11C C10C 1.396(3) . ?
C11C C12C 1.386(3) . ?
C10A C9A 1.395(3) . ?
C10A C13A 1.486(3) . ?
C10A C11A 1.396(3) . ?
C10C C13C 1.482(3) . ?
C10C C9C 1.398(3) . ?
C7A C8A 1.406(3) . ?
C7A C6A 1.484(3) . ?
C7A C12A 1.397(3) . ?
C19A C18A 1.506(3) . ?
C5B H5B 0.9500 . ?
C5B C4B 1.387(3) . ?
C9A H9A 0.9500 . ?
C9A C8A 1.384(4) . ?
C12C H12C 0.9500 . ?
C12C C7C 1.397(3) . ?
C19C C18C 1.506(4) . ?
C14A C13A 1.509(3) . ?
C14A C18A 1.388(3) . ?
C14A C15A 1.395(3) . ?
C6C C7C 1.486(3) . ?
C6C C1C 1.397(3) . ?
C8A H8A 0.9500 . ?
C7B C8B 1.401(3) . ?
C7B C12B 1.406(3) . ?
C1B H1B 0.9500 . ?
C1B C2B 1.383(4) . ?
C6A C1A 1.393(3) . ?
C6A C5A 1.399(3) . ?
C14C C18C 1.394(3) . ?
C14C C13C 1.517(3) . ?
C14C C15C 1.392(4) . ?
C8B H8B 0.9500 . ?
C8B C9B 1.380(3) . ?
C7C C8C 1.400(3) . ?
C9B H9B 0.9500 . ?
C9B C10B 1.401(3) . ?
C14B C18B 1.397(3) . ?
C14B C15B 1.389(4) . ?
C14B C13B 1.508(3) . ?
C1C H1C 0.9500 . ?
C1C C2C 1.388(3) . ?
C10B C11B 1.398(3) . ?
C10B C13B 1.484(3) . ?
C4B H4B 0.9500 . ?
C4B C3B 1.390(4) . ?
C3B H3B 0.9500 . ?
C3B C2B 1.388(4) . ?
C11B H11B 0.9500 . ?
C11B C12B 1.378(3) . ?
C4C H4C 0.9500 . ?
C4C C3C 1.384(4) . ?
C4A H4A 0.9500 . ?
C4A C3A 1.390(3) . ?
C4A C5A 1.386(4) . ?
C17A H17A 0.9500 . ?
C17A C16A 1.386(4) . ?
C18B C19B 1.511(4) . ?
C12A H12A 0.9500 . ?
C12A C11A 1.383(3) . ?
C16B H16B 0.9500 . ?
C16B C15B 1.381(4) . ?
C16B C17B 1.382(4) . ?
C15B H15B 0.9500 . ?
C12B H12B 0.9500 . ?
C1A H1A 0.9500 . ?
C1A C2A 1.386(4) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.382(4) . ?
C3A H3A 0.9500 . ?
C3A C2A 1.385(4) . ?
C3C H3C 0.9500 . ?
C3C C2C 1.390(4) . ?
C2B H2B 0.9500 . ?
C2A H2A 0.9500 . ?
C16A H16A 0.9500 . ?
C9C H9C 0.9500 . ?
C9C C8C 1.374(4) . ?
C17B H17B 0.9500 . ?
C8C H8C 0.9500 . ?
C11A H11A 0.9500 . ?
C2C H2C 0.9500 . ?
C5A H5A 0.9500 . ?
C15C H15C 0.9500 . ?
C15C C16C 1.376(4) . ?
C17C H17C 0.9500 . ?
C17C C16C 1.380(4) . ?
C16C H16C 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
C17A N1A C18A 116.9(2) . . ?
C17C N1C C18C 117.1(2) . . ?
C18B N1B C17B 116.9(2) . . ?
C5B C6B C7B 121.2(2) . . ?
C1B C6B C5B 117.7(2) . . ?
C1B C6B C7B 121.1(2) . . ?
C6C C5C H5C 119.6 . . ?
C4C C5C H5C 119.6 . . ?
C4C C5C C6C 120.9(2) . . ?
C10C C11C H11C 119.9 . . ?
C12C C11C H11C 119.9 . . ?
C12C C11C C10C 120.2(2) . . ?
C9A C10A C13A 119.0(2) . . ?
C9A C10A C11A 119.4(2) . . ?
C11A C10A C13A 121.4(2) . . ?
C11C C10C C13C 122.4(2) . . ?
C11C C10C C9C 119.2(2) . . ?
C9C C10C C13C 118.4(2) . . ?
C8A C7A C6A 121.4(2) . . ?
C12A C7A C8A 118.2(2) . . ?
C12A C7A C6A 120.4(2) . . ?
F1A C19A C18A 113.42(19) . . ?
F3A C19A F1A 106.00(19) . . ?
F3A C19A C18A 111.2(2) . . ?
F2A C19A F1A 107.0(2) . . ?
F2A C19A F3A 107.08(19) . . ?
F2A C19A C18A 111.7(2) . . ?
C6B C5B H5B 119.5 . . ?
C4B C5B C6B 121.1(2) . . ?
C4B C5B H5B 119.5 . . ?
C10A C9A H9A 119.9 . . ?
C8A C9A C10A 120.2(2) . . ?
C8A C9A H9A 119.9 . . ?
C11C C12C H12C 119.6 . . ?
C11C C12C C7C 120.7(2) . . ?
C7C C12C H12C 119.6 . . ?
F3C C19C F2C 105.9(2) . . ?
F3C C19C C18C 112.3(2) . . ?
F2C C19C C18C 112.27(19) . . ?
F1C C19C F3C 106.1(2) . . ?
F1C C19C F2C 106.8(2) . . ?
F1C C19C C18C 113.1(2) . . ?
C18A C14A C13A 123.9(2) . . ?
C18A C14A C15A 116.9(2) . . ?
C15A C14A C13A 119.0(2) . . ?
C5C C6C C7C 120.6(2) . . ?
C1C C6C C5C 118.3(2) . . ?
C1C C6C C7C 121.0(2) . . ?
C7A C8A H8A 119.6 . . ?
C9A C8A C7A 120.8(2) . . ?
C9A C8A H8A 119.6 . . ?
C8B C7B C6B 121.1(2) . . ?
C8B C7B C12B 117.9(2) . . ?
C12B C7B C6B 121.0(2) . . ?
C6B C1B H1B 119.3 . . ?
C2B C1B C6B 121.4(2) . . ?
C2B C1B H1B 119.3 . . ?
C1A C6A C7A 121.3(2) . . ?
C1A C6A C5A 118.2(2) . . ?
C5A C6A C7A 120.5(2) . . ?
C18C C14C C13C 123.7(2) . . ?
C15C C14C C18C 117.2(2) . . ?
C15C C14C C13C 118.8(2) . . ?
C7B C8B H8B 119.5 . . ?
C9B C8B C7B 121.1(2) . . ?
C9B C8B H8B 119.5 . . ?
C12C C7C C6C 121.0(2) . . ?
C12C C7C C8C 118.4(2) . . ?
C8C C7C C6C 120.6(2) . . ?
C8B C9B H9B 119.7 . . ?
C8B C9B C10B 120.7(2) . . ?
C10B C9B H9B 119.7 . . ?
C18B C14B C13B 122.9(2) . . ?
C15B C14B C18B 117.0(2) . . ?
C15B C14B C13B 120.0(2) . . ?
N1C C18C C19C 114.1(2) . . ?
N1C C18C C14C 124.1(2) . . ?
C14C C18C C19C 121.8(2) . . ?
O1A C13A C10A 122.2(2) . . ?
O1A C13A C14A 118.3(2) . . ?
C10A C13A C14A 119.51(19) . . ?
O1C C13C C10C 122.7(2) . . ?
O1C C13C C14C 117.9(2) . . ?
C10C C13C C14C 119.47(19) . . ?
C6C C1C H1C 119.7 . . ?
C2C C1C C6C 120.7(2) . . ?
C2C C1C H1C 119.7 . . ?
N1A C18A C19A 112.2(2) . . ?
N1A C18A C14A 124.8(2) . . ?
C14A C18A C19A 123.0(2) . . ?
C9B C10B C13B 122.1(2) . . ?
C11B C10B C9B 118.5(2) . . ?
C11B C10B C13B 119.3(2) . . ?
C5B C4B H4B 119.8 . . ?
C5B C4B C3B 120.3(2) . . ?
C3B C4B H4B 119.8 . . ?
C4B C3B H3B 120.4 . . ?
C2B C3B C4B 119.2(2) . . ?
C2B C3B H3B 120.4 . . ?
C10B C11B H11B 119.6 . . ?
C12B C11B C10B 120.7(2) . . ?
C12B C11B H11B 119.6 . . ?
C5C C4C H4C 119.9 . . ?
C3C C4C C5C 120.2(2) . . ?
C3C C4C H4C 119.9 . . ?
C3A C4A H4A 120.1 . . ?
C5A C4A H4A 120.1 . . ?
C5A C4A C3A 119.7(2) . . ?
N1A C17A H17A 118.5 . . ?
N1A C17A C16A 122.9(2) . . ?
C16A C17A H17A 118.5 . . ?
N1B C18B C14B 124.5(2) . . ?
N1B C18B C19B 113.7(2) . . ?
C14B C18B C19B 121.8(2) . . ?
C7A C12A H12A 119.5 . . ?
C11A C12A C7A 121.1(2) . . ?
C11A C12A H12A 119.5 . . ?
C15B C16B H16B 120.4 . . ?
C15B C16B C17B 119.2(2) . . ?
C17B C16B H16B 120.4 . . ?
C14B C15B H15B 120.4 . . ?
C16B C15B C14B 119.3(2) . . ?
C16B C15B H15B 120.4 . . ?
O1B C13B C14B 119.2(2) . . ?
O1B C13B C10B 122.5(2) . . ?
C10B C13B C14B 118.3(2) . . ?
C7B C12B H12B 119.5 . . ?
C11B C12B C7B 121.1(2) . . ?
C11B C12B H12B 119.5 . . ?
C6A C1A H1A 119.5 . . ?
C2A C1A C6A 121.0(2) . . ?
C2A C1A H1A 119.5 . . ?
C14A C15A H15A 120.5 . . ?
C16A C15A C14A 119.0(2) . . ?
C16A C15A H15A 120.5 . . ?
C4A C3A H3A 120.1 . . ?
C2A C3A C4A 119.8(2) . . ?
C2A C3A H3A 120.1 . . ?
C4C C3C H3C 120.2 . . ?
C4C C3C C2C 119.7(2) . . ?
C2C C3C H3C 120.2 . . ?
C1B C2B C3B 120.3(2) . . ?
C1B C2B H2B 119.9 . . ?
C3B C2B H2B 119.9 . . ?
C1A C2A H2A 119.9 . . ?
C3A C2A C1A 120.2(2) . . ?
C3A C2A H2A 119.9 . . ?
C17A C16A H16A 120.4 . . ?
C15A C16A C17A 119.2(2) . . ?
C15A C16A H16A 120.4 . . ?
C10C C9C H9C 119.8 . . ?
C8C C9C C10C 120.3(2) . . ?
C8C C9C H9C 119.8 . . ?
N1B C17B C16B 123.1(2) . . ?
N1B C17B H17B 118.5 . . ?
C16B C17B H17B 118.5 . . ?
C7C C8C H8C 119.4 . . ?
C9C C8C C7C 121.1(2) . . ?
C9C C8C H8C 119.4 . . ?
C10A C11A H11A 119.9 . . ?
C12A C11A C10A 120.2(2) . . ?
C12A C11A H11A 119.9 . . ?
F1B C19B C18B 112.3(2) . . ?
F2B C19B F1B 105.9(2) . . ?
F2B C19B C18B 112.2(2) . . ?
F3B C19B F1B 106.4(2) . . ?
F3B C19B F2B 107.2(2) . . ?
F3B C19B C18B 112.4(2) . . ?
C1C C2C C3C 120.3(2) . . ?
C1C C2C H2C 119.9 . . ?
C3C C2C H2C 119.9 . . ?
C6A C5A H5A 119.4 . . ?
C4A C5A C6A 121.1(2) . . ?
C4A C5A H5A 119.4 . . ?
C14C C15C H15C 120.4 . . ?
C16C C15C C14C 119.2(3) . . ?
C16C C15C H15C 120.4 . . ?
N1C C17C H17C 118.4 . . ?
N1C C17C C16C 123.3(2) . . ?
C16C C17C H17C 118.4 . . ?
C15C C16C C17C 119.0(3) . . ?
C15C C16C H16C 120.5 . . ?
C17C C16C H16C 120.5 . . ?

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
F1A C19A C18A N1A 177.32(19) . . . . ?
F1A C19A C18A C14A -2.1(3) . . . . ?
F3A C19A C18A N1A 57.9(3) . . . . ?
F3A C19A C18A C14A -121.5(2) . . . . ?
F3C C19C C18C N1C 93.6(3) . . . . ?
F3C C19C C18C C14C -84.0(3) . . . . ?
F2A C19A C18A N1A -61.6(3) . . . . ?
F2A C19A C18A C14A 118.9(2) . . . . ?
F2C C19C C18C N1C -147.2(2) . . . . ?
F2C C19C C18C C14C 35.2(3) . . . . ?
F1C C19C C18C N1C -26.3(3) . . . . ?
F1C C19C C18C C14C 156.1(2) . . . . ?
N1A C17A C16A C15A -3.6(4) . . . . ?
N1C C17C C16C C15C 0.9(5) . . . . ?
N1B C18B C19B F1B 149.6(2) . . . . ?
N1B C18B C19B F2B -91.3(3) . . . . ?
N1B C18B C19B F3B 29.6(3) . . . . ?
C6B C5B C4B C3B 0.5(3) . . . . ?
C6B C7B C8B C9B 179.1(2) . . . . ?
C6B C7B C12B C11B -178.4(2) . . . . ?
C6B C1B C2B C3B -0.7(4) . . . . ?
C5C C6C C7C C12C 141.4(2) . . . . ?
C5C C6C C7C C8C -38.6(3) . . . . ?
C5C C6C C1C C2C 0.6(3) . . . . ?
C5C C4C C3C C2C 0.3(4) . . . . ?
C11C C10C C13C O1C 180.0(2) . . . . ?
C11C C10C C13C C14C 0.3(4) . . . . ?
C11C C10C C9C C8C 2.1(4) . . . . ?
C11C C12C C7C C6C -178.7(2) . . . . ?
C11C C12C C7C C8C 1.3(3) . . . . ?
C10A C9A C8A C7A -0.4(4) . . . . ?
C10C C11C C12C C7C 0.2(3) . . . . ?
C10C C9C C8C C7C -0.6(4) . . . . ?
C7A C6A C1A C2A -174.2(2) . . . . ?
C7A C6A C5A C4A 174.5(2) . . . . ?
C7A C12A C11A C10A -0.2(4) . . . . ?
C5B C6B C7B C8B 29.5(3) . . . . ?
C5B C6B C7B C12B -151.2(2) . . . . ?
C5B C6B C1B C2B 0.3(4) . . . . ?
C5B C4B C3B C2B -0.9(4) . . . . ?
C9A C10A C13A O1A -2.4(3) . . . . ?
C9A C10A C13A C14A 177.7(2) . . . . ?
C9A C10A C11A C12A 2.7(4) . . . . ?
C12C C11C C10C C13C 175.7(2) . . . . ?
C12C C11C C10C C9C -1.9(4) . . . . ?
C12C C7C C8C C9C -1.1(4) . . . . ?
C14A C15A C16A C17A 1.3(4) . . . . ?
C6C C5C C4C C3C -0.1(4) . . . . ?
C6C C7C C8C C9C 178.9(2) . . . . ?
C6C C1C C2C C3C -0.4(4) . . . . ?
C8A C7A C6A C1A -151.4(2) . . . . ?
C8A C7A C6A C5A 32.6(3) . . . . ?
C8A C7A C12A C11A -2.5(4) . . . . ?
C7B C6B C5B C4B -179.7(2) . . . . ?
C7B C6B C1B C2B 179.9(2) . . . . ?
C7B C8B C9B C10B -1.0(4) . . . . ?
C1B C6B C5B C4B -0.2(3) . . . . ?
C1B C6B C7B C8B -150.0(2) . . . . ?
C1B C6B C7B C12B 29.2(3) . . . . ?
C6A C7A C8A C9A -174.3(2) . . . . ?
C6A C7A C12A C11A 174.6(2) . . . . ?
C6A C1A C2A C3A -0.7(4) . . . . ?
C14C C15C C16C C17C 0.3(4) . . . . ?
C8B C7B C12B C11B 0.9(3) . . . . ?
C8B C9B C10B C11B 1.4(4) . . . . ?
C8B C9B C10B C13B -175.2(2) . . . . ?
C7C C6C C1C C2C -179.0(2) . . . . ?
C9B C10B C11B C12B -0.6(4) . . . . ?
C9B C10B C13B O1B 175.1(2) . . . . ?
C9B C10B C13B C14B -4.3(3) . . . . ?
C14B C18B C19B F1B -30.4(3) . . . . ?
C14B C18B C19B F2B 88.7(3) . . . . ?
C14B C18B C19B F3B -150.3(2) . . . . ?
C18C N1C C17C C16C -1.0(4) . . . . ?
C18C C14C C13C O1C 83.1(3) . . . . ?
C18C C14C C13C C10C -97.2(3) . . . . ?
C18C C14C C15C C16C -1.3(4) . . . . ?
C13A C10A C9A C8A 173.6(2) . . . . ?
C13A C10A C11A C12A -173.2(2) . . . . ?
C13A C14A C18A N1A 170.6(2) . . . . ?
C13A C14A C18A C19A -10.1(3) . . . . ?
C13A C14A C15A C16A -172.6(2) . . . . ?
C13C C10C C9C C8C -175.6(2) . . . . ?
C13C C14C C18C N1C -173.2(2) . . . . ?
C13C C14C C18C C19C 4.2(4) . . . . ?
C13C C14C C15C C16C 173.4(2) . . . . ?
C1C C6C C7C C12C -38.9(3) . . . . ?
C1C C6C C7C C8C 141.1(2) . . . . ?
C18A N1A C17A C16A 2.0(4) . . . . ?
C18A C14A C13A O1A -84.1(3) . . . . ?
C18A C14A C13A C10A 95.8(3) . . . . ?
C18A C14A C15A C16A 2.1(3) . . . . ?
C10B C11B C12B C7B -0.5(4) . . . . ?
C4B C3B C2B C1B 1.0(4) . . . . ?
C11B C10B C13B O1B -1.4(4) . . . . ?
C11B C10B C13B C14B 179.2(2) . . . . ?
C4C C5C C6C C7C 179.3(2) . . . . ?
C4C C5C C6C C1C -0.3(3) . . . . ?
C4C C3C C2C C1C -0.1(4) . . . . ?
C4A C3A C2A C1A -1.0(4) . . . . ?
C17A N1A C18A C19A -177.6(2) . . . . ?
C17A N1A C18A C14A 1.9(3) . . . . ?
C18B N1B C17B C16B 1.8(4) . . . . ?
C18B C14B C15B C16B 2.0(3) . . . . ?
C18B C14B C13B O1B -69.1(3) . . . . ?
C18B C14B C13B C10B 110.3(3) . . . . ?
C12A C7A C8A C9A 2.8(4) . . . . ?
C12A C7A C6A C1A 31.6(3) . . . . ?
C12A C7A C6A C5A -144.4(2) . . . . ?
C15B C14B C18B N1B -1.7(4) . . . . ?
C15B C14B C18B C19B 178.3(2) . . . . ?
C15B C14B C13B O1B 108.0(3) . . . . ?
C15B C14B C13B C10B -72.6(3) . . . . ?
C15B C16B C17B N1B -1.5(4) . . . . ?
C13B C14B C18B N1B 175.5(2) . . . . ?
C13B C14B C18B C19B -4.5(4) . . . . ?
C13B C14B C15B C16B -175.4(2) . . . . ?
C13B C10B C11B C12B 176.0(2) . . . . ?
C12B C7B C8B C9B -0.1(3) . . . . ?
C1A C6A C5A C4A -1.7(3) . . . . ?
C15A C14A C13A O1A 90.3(3) . . . . ?
C15A C14A C13A C10A -89.9(3) . . . . ?
C15A C14A C18A N1A -3.9(3) . . . . ?
C15A C14A C18A C19A 175.5(2) . . . . ?
C3A C4A C5A C6A 0.1(4) . . . . ?
C9C C10C C13C O1C -2.4(4) . . . . ?
C9C C10C C13C C14C 178.0(2) . . . . ?
C17B N1B C18B C14B -0.2(3) . . . . ?
C17B N1B C18B C19B 179.9(2) . . . . ?
C17B C16B C15B C14B -0.5(4) . . . . ?
C11A C10A C9A C8A -2.3(4) . . . . ?
C11A C10A C13A O1A 173.4(2) . . . . ?
C11A C10A C13A C14A -6.4(3) . . . . ?
C5A C6A C1A C2A 2.0(3) . . . . ?
C5A C4A C3A C2A 1.3(4) . . . . ?
C15C C14C C18C N1C 1.3(4) . . . . ?
C15C C14C C18C C19C 178.7(2) . . . . ?
C15C C14C C13C O1C -91.3(3) . . . . ?
C15C C14C C13C C10C 88.4(3) . . . . ?
C17C N1C C18C C19C -177.7(2) . . . . ?
C17C N1C C18C C14C -0.2(4) . . . . ?

_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 1.266
_oxdiff_exptl_absorpt_empirical_full_min 0.819
####################################################################### 
# 
# 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_s6783r
_database_code_depnum_ccdc_archive 'CCDC 2515793'
loop_
_audit_author_name
_audit_author_address
' Avantika Hasija'
;The University of Manchester
United Kingdom
;
_audit_update_record             
;
2025-12-14 deposited with the CCDC.	2026-06-08 downloaded from the CCDC.
;
_audit_creation_date             2025-11-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H11 F3 N2 O2'
_chemical_formula_sum            'C19 H11 F3 N2 O2'
_chemical_formula_weight         356.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         C19H11F3N2O2
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      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                   14.7181(2)
_cell_length_b                   7.14966(9)
_cell_length_c                   15.2683(2)
_cell_angle_alpha                90
_cell_angle_beta                 108.6911(14)
_cell_angle_gamma                90
_cell_volume                     1521.94(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7699
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      77.1020
_cell_measurement_theta_min      3.0370
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.094
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.924
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.112a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0588
-1 0 0 0.0532
-1 0 2 0.0582
-2 -1 1 0.0630
2 1 -1 0.0551
0 0 -1 0.0792
0 1 2 0.0801
0 1 0 0.0672
0 1 -2 0.0839
-1 -1 1 0.0694
-2 -2 -1 0.0725
2 -1 0 0.0582
2 2 -1 0.0475

_exptl_crystal_size_max          0.175
_exptl_crystal_size_mid          0.151
_exptl_crystal_size_min          0.112
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0009 0.0002 -0.0003 0.0751 0.0696 0.0418
-1.0009 -0.0002 0.0003 -0.0751 -0.0696 -0.0418
-0.9989 0.0004 1.9984 -0.0592 -0.1042 0.1677
-2.0004 -1.0003 0.9997 0.0125 -0.3020 -0.0147
2.0004 1.0003 -0.9997 -0.0125 0.3020 0.0147
-0.0010 -0.0003 -0.9991 -0.0080 0.0173 -0.1047
0.0016 1.0008 1.9981 -0.1388 0.1110 0.2453
-0.0004 1.0003 0.0000 -0.1548 0.1456 0.0358
-0.0025 0.9997 -1.9981 -0.1708 0.1802 -0.1736
-0.9994 -1.0002 0.9994 0.0877 -0.2324 0.0271
-2.0020 -2.0012 -0.9984 0.1514 -0.4130 -0.2599
2.0023 -0.9999 -0.0007 0.3051 -0.0065 0.0477
1.9999 2.0006 -0.9997 -0.1674 0.4476 0.0505

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9873
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.602
_diffrn_reflns_theta_min         3.170
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -24.00  20.00   0.50    0.05    --   46.64 -19.00   0.00   88
  2  ω     26.00  51.00   0.50    0.05    --   46.64-115.00 -87.00   50
  3  ω     48.00  73.00   0.50    0.05    --  107.75-115.00 -87.00   50
  4  ω     35.00 104.00   0.50    0.05    --  107.75 -95.00 -90.00  138
  5  ω     36.00  62.00   0.50    0.05    --  107.75 -61.00 -60.00   52
  6  ω     95.00 172.00   0.50    0.05    --  107.75  45.00   0.00  154
  7  ω    104.00 129.00   0.50    0.05    --  107.75 115.00   1.00   50
  8  ω     71.00  97.00   0.50    0.05    --  107.75 174.00 141.00   52
  9  ω     72.00 114.00   0.50    0.05    --   46.64 174.00 141.00   84
 10  ω     -5.00  21.00   0.50    0.05    --  -46.64  19.00 -90.00   52
 11  ω    -20.00  28.00   0.50    0.05    --  -46.64  19.00 -30.00   96
 12  ω    -22.00  29.00   0.50    0.05    --  -46.64  19.00 -60.00  102
 13  ω    -13.00  29.00   0.50    0.05    --  -46.64  19.00-180.00   84
 14  ω   -104.00 -75.00   0.50    0.05    -- -109.00 125.00 -60.00   58
 15  ω   -108.00 -44.00   0.50    0.05    -- -109.00 115.00   1.00  128
 16  ω    -63.00 -37.00   0.50    0.05    -- -109.00  61.00  90.00   52
 17  ω    -71.00 -40.00   0.50    0.05    -- -109.00  61.00  30.00   62
 18  ω    -71.00 -41.00   0.50    0.05    -- -109.00  61.00   0.00   60
 19  ω    -69.00 -37.00   0.50    0.05    -- -109.00  61.00 -30.00   64
 20  ω    -65.00 -40.00   0.50    0.05    -- -109.00  61.00 -60.00   50
 21  ω    -82.00 -52.00   0.50    0.05    --  -46.64 115.00   1.00   60
 22  ω    -65.00 -36.00   0.50    0.05    -- -109.00  61.00-180.00   58
 23  ω   -150.00-124.00   0.50    0.05    -- -109.00 -30.00 -60.00   52
 24  ω   -174.00 -98.00   0.50    0.05    -- -109.00 -45.00-180.00  152
 25  ω   -117.00 -61.00   0.50    0.05    --  -46.64-174.00 131.00  112
 26  ω   -101.00 -69.00   0.50    0.05    -- -109.00-174.00 131.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0750984000
_diffrn_orient_matrix_UB_12      -0.1547529000
_diffrn_orient_matrix_UB_13      0.0079622000
_diffrn_orient_matrix_UB_21      0.0694640000
_diffrn_orient_matrix_UB_22      0.1455631000
_diffrn_orient_matrix_UB_23      -0.0174289000
_diffrn_orient_matrix_UB_31      0.0417547000
_diffrn_orient_matrix_UB_32      0.0358530000
_diffrn_orient_matrix_UB_33      0.1047625000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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                2863
_reflns_number_total             3120
_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 1.171.43.112a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 44.122a 64-bit (release 14-09-2025))'
_computing_data_reduction        'CrysAlisPro 1.171.43.112a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0330
_refine_ls_restrained_S_all      1.043
_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)+(0.0404P)²+0.7208P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0856
_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:
 C15(H15), C10(H10), C3(H3), C12(H12), C11(H11), C16(H16), C4(H4), C17(H17)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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
F1 F 0.79969(7) 0.13267(12) 0.57485(5) 0.0327(2) Uani 1 1 d . . . . .
F2 F 0.85410(6) -0.07149(12) 0.68094(6) 0.0374(2) Uani 1 1 d . . . . .
F3 F 0.71522(6) 0.04653(14) 0.65824(6) 0.0373(2) Uani 1 1 d . . . . .
O1 O 0.69750(6) 0.55727(12) 0.63576(6) 0.01666(18) Uani 1 1 d . . . . .
O2 O 0.96065(6) 0.40546(14) 0.59468(6) 0.0241(2) Uani 1 1 d . . . . .
N1 N 0.55999(7) 0.59969(14) 0.67848(7) 0.0180(2) Uani 1 1 d . . . . .
N2 N 0.85002(8) 0.19290(16) 0.81568(7) 0.0225(2) Uani 1 1 d . . . . .
C14 C 0.88376(8) 0.40577(17) 0.70752(8) 0.0157(2) Uani 1 1 d . . . . .
C15 C 0.92297(8) 0.53256(18) 0.77912(8) 0.0190(3) Uani 1 1 d . . . . .
H15 H 0.947429 0.649234 0.766982 0.023 Uiso 1 1 calc R U . . .
C5 C 0.57213(8) 0.71220(17) 0.53150(8) 0.0172(2) Uani 1 1 d . . . . .
C6 C 0.60503(8) 0.62462(17) 0.61754(8) 0.0165(2) Uani 1 1 d . . . . .
C13 C 0.88944(8) 0.45321(17) 0.61293(8) 0.0169(2) Uani 1 1 d . . . . .
C8 C 0.72374(8) 0.60505(16) 0.55946(8) 0.0156(2) Uani 1 1 d . . . . .
C18 C 0.84848(8) 0.23867(17) 0.73047(8) 0.0170(2) Uani 1 1 d . . . . .
C7 C 0.65013(8) 0.70196(16) 0.49336(8) 0.0169(2) Uani 1 1 d . . . . .
C10 C 0.82267(9) 0.62262(18) 0.46373(8) 0.0196(3) Uani 1 1 d . . . . .
H10 H 0.881096 0.596593 0.452177 0.024 Uiso 1 1 calc R U . . .
C9 C 0.81112(8) 0.56145(17) 0.54677(8) 0.0167(2) Uani 1 1 d . . . . .
C3 C 0.42777(9) 0.75604(18) 0.56654(9) 0.0212(3) Uani 1 1 d . . . . .
H3 H 0.363793 0.801011 0.550693 0.025 Uiso 1 1 calc R U . . .
C2 C 0.46937(9) 0.66778(17) 0.65204(9) 0.0197(3) Uani 1 1 d . . . . .
C12 C 0.66413(9) 0.76124(17) 0.41165(8) 0.0199(3) Uani 1 1 d . . . . .
H12 H 0.615420 0.828131 0.366403 0.024 Uiso 1 1 calc R U . . .
C19 C 0.80434(9) 0.08681(18) 0.66094(8) 0.0195(3) Uani 1 1 d . . . . .
C11 C 0.75090(9) 0.72040(18) 0.39775(8) 0.0214(3) Uani 1 1 d . . . . .
H11 H 0.761350 0.759886 0.342338 0.026 Uiso 1 1 calc R U . . .
C16 C 0.92587(9) 0.48670(19) 0.86792(8) 0.0223(3) Uani 1 1 d . . . . .
H16 H 0.952810 0.570618 0.917736 0.027 Uiso 1 1 calc R U . . .
C4 C 0.47829(9) 0.77886(17) 0.50474(9) 0.0203(3) Uani 1 1 d . . . . .
H4 H 0.450084 0.837572 0.446510 0.024 Uiso 1 1 calc R U . . .
C17 C 0.88869(10) 0.3158(2) 0.88293(8) 0.0248(3) Uani 1 1 d . . . . .
H17 H 0.890919 0.284899 0.944104 0.030 Uiso 1 1 calc R U . . .
C1 C 0.41540(9) 0.6466(2) 0.71989(9) 0.0244(3) Uani 1 1 d . . . . .
H1A H 0.437119 0.533327 0.756828 0.037 Uiso 1 1 calc R U . . .
H1B H 0.346595 0.636777 0.686359 0.037 Uiso 1 1 calc R U . . .
H1C H 0.427278 0.755836 0.760779 0.037 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 C19 1.3351(15) . ?
F2 C19 1.3293(15) . ?
F3 C19 1.3306(14) . ?
O1 C6 1.3854(14) . ?
O1 C8 1.3825(14) . ?
O2 C13 1.2165(15) . ?
N1 C6 1.3160(16) . ?
N1 C2 1.3542(15) . ?
N2 C18 1.3347(16) . ?
N2 C17 1.3326(17) . ?
C14 C15 1.3949(17) . ?
C14 C13 1.5117(16) . ?
C14 C18 1.3916(17) . ?
C15 H15 0.9500 . ?
C15 C16 1.3821(17) . ?
C5 C6 1.3945(17) . ?
C5 C7 1.4461(17) . ?
C5 C4 1.3928(17) . ?
C13 C9 1.4839(16) . ?
C8 C7 1.4041(16) . ?
C8 C9 1.3958(16) . ?
C18 C19 1.5119(17) . ?
C7 C12 1.3939(17) . ?
C10 H10 0.9500 . ?
C10 C9 1.4021(17) . ?
C10 C11 1.3918(18) . ?
C3 H3 0.9500 . ?
C3 C2 1.4017(18) . ?
C3 C4 1.3855(18) . ?
C2 C1 1.5015(17) . ?
C12 H12 0.9500 . ?
C12 C11 1.3912(18) . ?
C11 H11 0.9500 . ?
C16 H16 0.9500 . ?
C16 C17 1.3877(19) . ?
C4 H4 0.9500 . ?
C17 H17 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?

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
C8 O1 C6 105.46(9) . . ?
C6 N1 C2 114.31(10) . . ?
C17 N2 C18 117.33(11) . . ?
C15 C14 C13 117.86(11) . . ?
C18 C14 C15 117.04(11) . . ?
C18 C14 C13 124.93(11) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 C14 119.31(12) . . ?
C16 C15 H15 120.3 . . ?
C6 C5 C7 106.01(10) . . ?
C4 C5 C6 116.25(11) . . ?
C4 C5 C7 137.72(11) . . ?
O1 C6 C5 111.56(10) . . ?
N1 C6 O1 119.73(10) . . ?
N1 C6 C5 128.70(11) . . ?
O2 C13 C14 118.12(11) . . ?
O2 C13 C9 121.93(11) . . ?
C9 C13 C14 119.91(10) . . ?
O1 C8 C7 111.60(10) . . ?
O1 C8 C9 125.47(10) . . ?
C9 C8 C7 122.92(11) . . ?
N2 C18 C14 124.39(11) . . ?
N2 C18 C19 112.19(11) . . ?
C14 C18 C19 123.42(11) . . ?
C8 C7 C5 105.35(10) . . ?
C12 C7 C5 135.16(11) . . ?
C12 C7 C8 119.48(11) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C11 C10 C9 121.83(12) . . ?
C8 C9 C13 124.85(11) . . ?
C8 C9 C10 116.10(11) . . ?
C10 C9 C13 119.04(11) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C4 C3 C2 121.18(11) . . ?
N1 C2 C3 122.27(11) . . ?
N1 C2 C1 116.51(11) . . ?
C3 C2 C1 121.21(11) . . ?
C7 C12 H12 120.7 . . ?
C11 C12 C7 118.62(11) . . ?
C11 C12 H12 120.7 . . ?
F1 C19 C18 112.95(10) . . ?
F2 C19 F1 106.61(10) . . ?
F2 C19 F3 106.73(11) . . ?
F2 C19 C18 111.65(10) . . ?
F3 C19 F1 106.48(10) . . ?
F3 C19 C18 112.01(10) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 121.05(11) . . ?
C12 C11 H11 119.5 . . ?
C15 C16 H16 120.6 . . ?
C15 C16 C17 118.76(12) . . ?
C17 C16 H16 120.6 . . ?
C5 C4 H4 121.4 . . ?
C3 C4 C5 117.26(11) . . ?
C3 C4 H4 121.4 . . ?
N2 C17 C16 123.16(12) . . ?
N2 C17 H17 118.4 . . ?
C16 C17 H17 118.4 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
O1 C8 C7 C5 -0.83(13) . . . . ?
O1 C8 C7 C12 180.00(10) . . . . ?
O1 C8 C9 C13 1.17(19) . . . . ?
O1 C8 C9 C10 179.61(11) . . . . ?
O2 C13 C9 C8 173.50(12) . . . . ?
O2 C13 C9 C10 -4.90(18) . . . . ?
N2 C18 C19 F1 178.16(10) . . . . ?
N2 C18 C19 F2 -61.70(14) . . . . ?
N2 C18 C19 F3 57.94(14) . . . . ?
C14 C15 C16 C17 -0.58(18) . . . . ?
C14 C13 C9 C8 -8.88(18) . . . . ?
C14 C13 C9 C10 172.72(11) . . . . ?
C14 C18 C19 F1 -2.24(17) . . . . ?
C14 C18 C19 F2 117.90(13) . . . . ?
C14 C18 C19 F3 -122.46(12) . . . . ?
C15 C14 C13 O2 87.89(14) . . . . ?
C15 C14 C13 C9 -89.82(13) . . . . ?
C15 C14 C18 N2 -0.12(18) . . . . ?
C15 C14 C18 C19 -179.67(11) . . . . ?
C15 C16 C17 N2 -0.1(2) . . . . ?
C5 C7 C12 C11 -178.20(13) . . . . ?
C6 O1 C8 C7 0.26(13) . . . . ?
C6 O1 C8 C9 -178.59(11) . . . . ?
C6 N1 C2 C3 0.36(17) . . . . ?
C6 N1 C2 C1 -178.77(11) . . . . ?
C6 C5 C7 C8 1.06(13) . . . . ?
C6 C5 C7 C12 -179.97(13) . . . . ?
C6 C5 C4 C3 1.50(17) . . . . ?
C13 C14 C15 C16 -174.86(11) . . . . ?
C13 C14 C18 N2 175.05(11) . . . . ?
C13 C14 C18 C19 -4.50(18) . . . . ?
C8 O1 C6 N1 179.87(11) . . . . ?
C8 O1 C6 C5 0.46(13) . . . . ?
C8 C7 C12 C11 0.66(18) . . . . ?
C18 N2 C17 C16 0.59(19) . . . . ?
C18 C14 C15 C16 0.66(17) . . . . ?
C18 C14 C13 O2 -87.25(15) . . . . ?
C18 C14 C13 C9 95.04(14) . . . . ?
C7 C5 C6 O1 -0.97(13) . . . . ?
C7 C5 C6 N1 179.69(12) . . . . ?
C7 C5 C4 C3 179.49(14) . . . . ?
C7 C8 C9 C13 -177.55(11) . . . . ?
C7 C8 C9 C10 0.89(17) . . . . ?
C7 C12 C11 C10 -0.06(19) . . . . ?
C9 C8 C7 C5 178.05(11) . . . . ?
C9 C8 C7 C12 -1.12(18) . . . . ?
C9 C10 C11 C12 -0.1(2) . . . . ?
C2 N1 C6 O1 -178.56(10) . . . . ?
C2 N1 C6 C5 0.74(18) . . . . ?
C2 C3 C4 C5 -0.60(18) . . . . ?
C11 C10 C9 C13 178.28(11) . . . . ?
C11 C10 C9 C8 -0.26(18) . . . . ?
C4 C5 C6 O1 177.63(10) . . . . ?
C4 C5 C6 N1 -1.72(19) . . . . ?
C4 C5 C7 C8 -177.07(14) . . . . ?
C4 C5 C7 C12 1.9(3) . . . . ?
C4 C3 C2 N1 -0.40(19) . . . . ?
C4 C3 C2 C1 178.69(12) . . . . ?
C17 N2 C18 C14 -0.49(18) . . . . ?
C17 N2 C18 C19 179.10(11) . . . . ?

_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 1.115
_oxdiff_exptl_absorpt_empirical_full_min 0.939
####################################################################### 
# 
# 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_s6746l
_database_code_depnum_ccdc_archive 'CCDC 2487297'
loop_
_audit_author_name
_audit_author_address
'Avantika Hasija'
;The University of Manchester
United Kingdom
;
_audit_update_record             
;
2025-09-11 deposited with the CCDC.	2026-06-08 downloaded from the CCDC.
;
_audit_creation_date             2025-09-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H23 N O'
_chemical_formula_sum            'C25 H23 N O'
_chemical_formula_weight         353.44
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
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'
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/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                   10.29270(10)
_cell_length_b                   20.50005(19)
_cell_length_c                   18.53109(19)
_cell_angle_alpha                90
_cell_angle_beta                 90.1212(9)
_cell_angle_gamma                90
_cell_volume                     3910.07(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8448
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      75.6640
_cell_measurement_theta_min      4.7240
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.561
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.931
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.112a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
6 2 3 0.0291
-6 -2 -3 0.0436
-2 9 8 0.0109
2 -9 -8 0.0363
0 11 -7 0.0218
0 -11 7 0.0218

_exptl_crystal_size_max          0.073
_exptl_crystal_size_mid          0.052
_exptl_crystal_size_min          0.044
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
6.3152 2.1791 3.3412 -0.0005 0.0006 -1.0000
-6.3152 -2.1791 -3.3412 0.0005 -0.0006 1.0000
-2.1215 8.6863 8.2962 -0.1170 -0.9931 -0.0005
2.1215 -8.6863 -8.2962 0.1170 0.9931 0.0005
0.2443 10.6924 -7.1437 0.9755 -0.2202 -0.0011
-0.2443 -10.6924 7.1437 -0.9755 0.2202 0.0011

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21995
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        66.600
_diffrn_reflns_theta_max         66.599
_diffrn_reflns_theta_min         3.215
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -5.00  21.00   0.50    0.75    --   43.87  30.00  30.00   52
  2  ω     22.00 133.00   0.50    0.75    --   43.87  30.00  30.00  222
  3  ω      8.00 135.00   0.50    0.75    --   46.33  60.00   0.00  254
  4  ω    -34.00  -6.00   0.50    0.75    --   46.33   0.00-180.00   56
  5  ω    161.00 198.00   0.50    4.00    --  108.20  40.00 -30.00   74
  6  ω     19.00  45.00   0.50    4.00    --  108.20  50.00 -60.00   52
  7  ω     23.00 198.00   0.50    4.00    --  108.20  60.00 -60.00  350
  8  ω     48.00 111.00   0.50    4.00    --  108.20  20.00  30.00  126
  9  ω    137.00 198.00   0.50    4.00    --  108.20  50.00 -60.00  122
 10  ω     94.00 120.00   0.50    4.00    --  108.20  50.00 -60.00   52
 11  ω     78.00 198.00   0.50    4.00    --  108.20  60.00 150.00  240
 12  ω     59.00 198.00   0.50    4.00    --  108.20  40.00 150.00  278
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0156098000
_diffrn_orient_matrix_UB_12      0.0494939000
_diffrn_orient_matrix_UB_13      -0.0619338000
_diffrn_orient_matrix_UB_21      0.0457090000
_diffrn_orient_matrix_UB_22      -0.0551954000
_diffrn_orient_matrix_UB_23      -0.0502295000
_diffrn_orient_matrix_UB_31      -0.1417370000
_diffrn_orient_matrix_UB_32      -0.0124271000
_diffrn_orient_matrix_UB_33      -0.0232928000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5486
_reflns_number_total             6625
_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 1.171.43.112a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 44.117a 64-bit (release 07-07-2025))'
_computing_data_reduction        'CrysAlisPro 1.171.43.112a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     487
_refine_ls_number_reflns         6625
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0405
_refine_ls_restrained_S_all      1.019
_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)+(0.0498P)²+0.8042P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1047
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C19B(H19A,H19B), C12B(H12A,H12B), C19A(H19C,H19D), C12A(H12C,H12D)
2.b Aromatic/amide H refined with riding coordinates:
 C8B(H8B), C11A(H11A), C11B(H11B), C10B(H10B), C9B(H9B), C5A(H5A), C10A(H10A),
 C4A(H4A), C1B(H1B), C9A(H9A), C18B(H18B), C8A(H8A), C21B(H21B), C25B(H25B),
 C14B(H14B), C25A(H25A), C5B(H5B), C3A(H3A), C1A(H1A), C2B(H2B), C14A(H14A),
 C15A(H15A), C18A(H18A), C24A(H24A), C16A(H16A), C17B(H17B), C15B(H15B),
 C2A(H2A), C4B(H4B), C21A(H21A), C16B(H16B), C3B(H3B), C23A(H23A), C22B(H22B),
 C24B(H24B), C17A(H17A), C23B(H23B), C22A(H22A)
;
_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
O1B O 1.04303(10) 0.35881(5) 0.01227(6) 0.0414(3) Uani 1 1 d . . . . .
O1A O 0.42860(10) 0.39920(5) 0.40155(6) 0.0408(3) Uani 1 1 d . . . . .
N1B N 0.64193(11) 0.58717(6) 0.07230(7) 0.0314(3) Uani 1 1 d . . . . .
N1A N 0.22621(12) 0.57092(6) 0.66856(7) 0.0337(3) Uani 1 1 d . . . . .
C20B C 0.60529(13) 0.68704(7) -0.00087(8) 0.0306(3) Uani 1 1 d . . . . .
C8B C 0.82095(14) 0.36737(7) 0.04308(8) 0.0314(3) Uani 1 1 d . . . . .
H8B H 0.743021 0.344033 0.052385 0.038 Uiso 1 1 calc R U . . .
C11A C 0.27799(14) 0.53879(7) 0.61294(8) 0.0327(3) Uani 1 1 d . . . . .
H11A H 0.369889 0.540730 0.608806 0.039 Uiso 1 1 calc R U . . .
C11B C 0.73054(13) 0.54122(7) 0.05684(7) 0.0299(3) Uani 1 1 d . . . . .
H11B H 0.813392 0.556378 0.041794 0.036 Uiso 1 1 calc R U . . .
C10B C 0.71501(13) 0.47516(7) 0.06030(8) 0.0309(3) Uani 1 1 d . . . . .
H10B H 0.634324 0.457206 0.075206 0.037 Uiso 1 1 calc R U . . .
C9B C 0.81891(14) 0.43359(7) 0.04171(7) 0.0311(3) Uani 1 1 d . . . . .
H9B H 0.896626 0.454369 0.026426 0.037 Uiso 1 1 calc R U . . .
C19B C 0.67146(14) 0.65635(7) 0.06381(8) 0.0321(3) Uani 1 1 d . . . . .
H19A H 0.766621 0.661705 0.058870 0.038 Uiso 1 1 calc R U . . .
H19B H 0.644209 0.679831 0.107943 0.038 Uiso 1 1 calc R U . . .
C13B C 0.49353(14) 0.55761(7) 0.17387(8) 0.0333(3) Uani 1 1 d . . . . .
C5A C 0.13019(14) 0.30906(7) 0.38524(8) 0.0328(3) Uani 1 1 d . . . . .
H5A H 0.092556 0.320264 0.430334 0.039 Uiso 1 1 calc R U . . .
C10A C 0.21428(15) 0.50335(7) 0.56110(8) 0.0346(3) Uani 1 1 d . . . . .
H10A H 0.122025 0.501947 0.560814 0.042 Uiso 1 1 calc R U . . .
C12B C 0.51068(13) 0.56923(7) 0.09371(8) 0.0329(3) Uani 1 1 d . . . . .
H12A H 0.485448 0.529074 0.067520 0.039 Uiso 1 1 calc R U . . .
H12B H 0.450510 0.604338 0.078524 0.039 Uiso 1 1 calc R U . . .
C4A C 0.07218(15) 0.26156(7) 0.34251(8) 0.0363(3) Uani 1 1 d . . . . .
H4A H -0.004086 0.239926 0.358576 0.044 Uiso 1 1 calc R U . . .
C13A C 0.04038(14) 0.53513(7) 0.74351(8) 0.0341(3) Uani 1 1 d . . . . .
C1B C 1.05342(16) 0.23075(8) 0.07142(8) 0.0377(3) Uani 1 1 d . . . . .
H1B H 1.128939 0.256392 0.079497 0.045 Uiso 1 1 calc R U . . .
C7B C 0.94054(14) 0.33186(7) 0.03054(7) 0.0322(3) Uani 1 1 d . . . . .
C6A C 0.24314(14) 0.34043(7) 0.36256(8) 0.0343(3) Uani 1 1 d . . . . .
C9A C 0.28477(15) 0.46896(7) 0.50817(8) 0.0360(3) Uani 1 1 d . . . . .
H9A H 0.376429 0.474392 0.507640 0.043 Uiso 1 1 calc R U . . .
C18B C 0.57291(15) 0.58649(7) 0.22554(9) 0.0385(3) Uani 1 1 d . . . . .
H18B H 0.646517 0.611094 0.210946 0.046 Uiso 1 1 calc R U . . .
C6B C 0.94099(14) 0.25980(7) 0.04444(8) 0.0333(3) Uani 1 1 d . . . . .
C20A C 0.29142(14) 0.67758(7) 0.71664(8) 0.0329(3) Uani 1 1 d . . . . .
C19A C 0.30852(15) 0.60465(7) 0.72140(8) 0.0350(3) Uani 1 1 d . . . . .
H19C H 0.400673 0.593440 0.712534 0.042 Uiso 1 1 calc R U . . .
H19D H 0.285817 0.589737 0.770595 0.042 Uiso 1 1 calc R U . . .
C12A C 0.08606(14) 0.57621(7) 0.68075(9) 0.0371(3) Uani 1 1 d . . . . .
H12C H 0.039486 0.562376 0.636529 0.045 Uiso 1 1 calc R U . . .
H12D H 0.063754 0.622419 0.690048 0.045 Uiso 1 1 calc R U . . .
C8A C 0.23138(15) 0.42834(7) 0.45748(8) 0.0360(3) Uani 1 1 d . . . . .
H8A H 0.139516 0.424456 0.454891 0.043 Uiso 1 1 calc R U . . .
C21B C 0.58093(15) 0.65239(8) -0.06369(8) 0.0386(3) Uani 1 1 d . . . . .
H21B H 0.603345 0.607512 -0.066483 0.046 Uiso 1 1 calc R U . . .
C25B C 0.57182(14) 0.75282(7) 0.00184(9) 0.0370(3) Uani 1 1 d . . . . .
H25B H 0.585813 0.776866 0.044984 0.044 Uiso 1 1 calc R U . . .
C7A C 0.30985(15) 0.39136(7) 0.40800(8) 0.0348(3) Uani 1 1 d . . . . .
C14B C 0.38859(15) 0.52021(7) 0.19688(9) 0.0406(4) Uani 1 1 d . . . . .
H14B H 0.335315 0.498943 0.162185 0.049 Uiso 1 1 calc R U . . .
C25A C 0.22727(15) 0.71228(8) 0.77007(8) 0.0392(3) Uani 1 1 d . . . . .
H25A H 0.194250 0.689924 0.811022 0.047 Uiso 1 1 calc R U . . .
C5B C 0.83266(16) 0.22112(7) 0.03132(9) 0.0394(3) Uani 1 1 d . . . . .
H5B H 0.755415 0.240398 0.012993 0.047 Uiso 1 1 calc R U . . .
C3A C 0.12655(15) 0.24586(8) 0.27594(8) 0.0395(3) Uani 1 1 d . . . . .
H3A H 0.085798 0.214447 0.245754 0.047 Uiso 1 1 calc R U . . .
C1A C 0.29822(16) 0.32257(8) 0.29701(9) 0.0430(4) Uani 1 1 d . . . . .
H1A H 0.376769 0.342553 0.281728 0.052 Uiso 1 1 calc R U . . .
C2B C 1.05540(18) 0.16430(8) 0.08656(9) 0.0459(4) Uani 1 1 d . . . . .
H2B H 1.131454 0.144892 0.106205 0.055 Uiso 1 1 calc R U . . .
C14A C 0.07109(15) 0.46924(7) 0.74786(9) 0.0389(3) Uani 1 1 d . . . . .
H14A H 0.122543 0.449653 0.711292 0.047 Uiso 1 1 calc R U . . .
C15A C 0.02722(17) 0.43195(8) 0.80510(9) 0.0457(4) Uani 1 1 d . . . . .
H15A H 0.047887 0.386834 0.807379 0.055 Uiso 1 1 calc R U . . .
C18A C -0.03324(15) 0.56301(8) 0.79811(9) 0.0428(4) Uani 1 1 d . . . . .
H18A H -0.054405 0.608077 0.796065 0.051 Uiso 1 1 calc R U . . .
C24A C 0.21081(16) 0.77919(8) 0.76438(9) 0.0445(4) Uani 1 1 d . . . . .
H24A H 0.167481 0.802473 0.801552 0.053 Uiso 1 1 calc R U . . .
C16A C -0.04636(17) 0.46008(9) 0.85883(9) 0.0486(4) Uani 1 1 d . . . . .
H16A H -0.076508 0.434352 0.898013 0.058 Uiso 1 1 calc R U . . .
C17B C 0.54503(17) 0.57951(8) 0.29849(9) 0.0443(4) Uani 1 1 d . . . . .
H17B H 0.599544 0.599587 0.333451 0.053 Uiso 1 1 calc R U . . .
C15B C 0.36075(17) 0.51355(8) 0.26941(10) 0.0475(4) Uani 1 1 d . . . . .
H15B H 0.288068 0.488330 0.284145 0.057 Uiso 1 1 calc R U . . .
C2A C 0.23965(17) 0.27597(9) 0.25387(9) 0.0466(4) Uani 1 1 d . . . . .
H2A H 0.277418 0.264644 0.208845 0.056 Uiso 1 1 calc R U . . .
C4B C 0.83636(18) 0.15439(8) 0.04479(10) 0.0477(4) Uani 1 1 d . . . . .
H4B H 0.762611 0.128109 0.034477 0.057 Uiso 1 1 calc R U . . .
C21A C 0.33726(17) 0.71101(8) 0.65662(10) 0.0442(4) Uani 1 1 d . . . . .
H21A H 0.381070 0.687925 0.619471 0.053 Uiso 1 1 calc R U . . .
C16B C 0.43840(17) 0.54351(8) 0.32063(10) 0.0474(4) Uani 1 1 d . . . . .
H16B H 0.418803 0.539437 0.370500 0.057 Uiso 1 1 calc R U . . .
C3B C 0.94687(19) 0.12647(8) 0.07306(10) 0.0495(4) Uani 1 1 d . . . . .
H3B H 0.948584 0.081071 0.083324 0.059 Uiso 1 1 calc R U . . .
C23A C 0.25716(16) 0.81190(8) 0.70496(11) 0.0497(4) Uani 1 1 d . . . . .
H23A H 0.246501 0.857807 0.701137 0.060 Uiso 1 1 calc R U . . .
C22B C 0.52394(17) 0.68304(10) -0.12243(9) 0.0496(4) Uani 1 1 d . . . . .
H22B H 0.505156 0.658675 -0.164795 0.060 Uiso 1 1 calc R U . . .
C24B C 0.51830(16) 0.78347(9) -0.05784(10) 0.0472(4) Uani 1 1 d . . . . .
H24B H 0.498151 0.828654 -0.055879 0.057 Uiso 1 1 calc R U . . .
C17A C -0.07608(16) 0.52549(10) 0.85564(10) 0.0499(4) Uani 1 1 d . . . . .
H17A H -0.126047 0.544974 0.892907 0.060 Uiso 1 1 calc R U . . .
C23B C 0.49423(17) 0.74871(10) -0.11992(10) 0.0531(5) Uani 1 1 d . . . . .
H23B H 0.457402 0.769732 -0.160811 0.064 Uiso 1 1 calc R U . . .
C22A C 0.31952(19) 0.77756(9) 0.65065(11) 0.0536(5) Uani 1 1 d . . . . .
H22A H 0.350178 0.799921 0.609137 0.064 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
O1B C7B 1.2386(18) . ?
O1A C7A 1.2388(18) . ?
N1B C11B 1.3426(18) . ?
N1B C19B 1.4590(18) . ?
N1B C12B 1.4561(18) . ?
N1A C11A 1.3351(19) . ?
N1A C19A 1.4666(18) . ?
N1A C12A 1.4646(19) . ?
C20B C19B 1.514(2) . ?
C20B C21B 1.386(2) . ?
C20B C25B 1.393(2) . ?
C8B H8B 0.9500 . ?
C8B C9B 1.358(2) . ?
C8B C7B 1.449(2) . ?
C11A H11A 0.9500 . ?
C11A C10A 1.370(2) . ?
C11B H11B 0.9500 . ?
C11B C10B 1.365(2) . ?
C10B H10B 0.9500 . ?
C10B C9B 1.411(2) . ?
C9B H9B 0.9500 . ?
C19B H19A 0.9900 . ?
C19B H19B 0.9900 . ?
C13B C12B 1.515(2) . ?
C13B C18B 1.390(2) . ?
C13B C14B 1.392(2) . ?
C5A H5A 0.9500 . ?
C5A C4A 1.389(2) . ?
C5A C6A 1.394(2) . ?
C10A H10A 0.9500 . ?
C10A C9A 1.410(2) . ?
C12B H12A 0.9900 . ?
C12B H12B 0.9900 . ?
C4A H4A 0.9500 . ?
C4A C3A 1.393(2) . ?
C13A C12A 1.512(2) . ?
C13A C14A 1.390(2) . ?
C13A C18A 1.388(2) . ?
C1B H1B 0.9500 . ?
C1B C6B 1.393(2) . ?
C1B C2B 1.391(2) . ?
C7B C6B 1.500(2) . ?
C6A C7A 1.506(2) . ?
C6A C1A 1.391(2) . ?
C9A H9A 0.9500 . ?
C9A C8A 1.370(2) . ?
C18B H18B 0.9500 . ?
C18B C17B 1.390(2) . ?
C6B C5B 1.389(2) . ?
C20A C19A 1.508(2) . ?
C20A C25A 1.387(2) . ?
C20A C21A 1.390(2) . ?
C19A H19C 0.9900 . ?
C19A H19D 0.9900 . ?
C12A H12C 0.9900 . ?
C12A H12D 0.9900 . ?
C8A H8A 0.9500 . ?
C8A C7A 1.439(2) . ?
C21B H21B 0.9500 . ?
C21B C22B 1.386(2) . ?
C25B H25B 0.9500 . ?
C25B C24B 1.385(2) . ?
C14B H14B 0.9500 . ?
C14B C15B 1.382(3) . ?
C25A H25A 0.9500 . ?
C25A C24A 1.386(2) . ?
C5B H5B 0.9500 . ?
C5B C4B 1.391(2) . ?
C3A H3A 0.9500 . ?
C3A C2A 1.380(2) . ?
C1A H1A 0.9500 . ?
C1A C2A 1.383(2) . ?
C2B H2B 0.9500 . ?
C2B C3B 1.382(3) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.384(2) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.379(3) . ?
C18A H18A 0.9500 . ?
C18A C17A 1.387(3) . ?
C24A H24A 0.9500 . ?
C24A C23A 1.376(3) . ?
C16A H16A 0.9500 . ?
C16A C17A 1.377(3) . ?
C17B H17B 0.9500 . ?
C17B C16B 1.385(3) . ?
C15B H15B 0.9500 . ?
C15B C16B 1.383(3) . ?
C2A H2A 0.9500 . ?
C4B H4B 0.9500 . ?
C4B C3B 1.376(3) . ?
C21A H21A 0.9500 . ?
C21A C22A 1.381(3) . ?
C16B H16B 0.9500 . ?
C3B H3B 0.9500 . ?
C23A H23A 0.9500 . ?
C23A C22A 1.387(3) . ?
C22B H22B 0.9500 . ?
C22B C23B 1.381(3) . ?
C24B H24B 0.9500 . ?
C24B C23B 1.375(3) . ?
C17A H17A 0.9500 . ?
C23B H23B 0.9500 . ?
C22A H22A 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
C11B N1B C19B 121.15(12) . . ?
C11B N1B C12B 120.79(12) . . ?
C12B N1B C19B 117.95(11) . . ?
C11A N1A C19A 121.13(12) . . ?
C11A N1A C12A 123.40(12) . . ?
C12A N1A C19A 115.46(12) . . ?
C21B C20B C19B 122.15(13) . . ?
C21B C20B C25B 118.83(14) . . ?
C25B C20B C19B 118.99(13) . . ?
C9B C8B H8B 119.6 . . ?
C9B C8B C7B 120.81(13) . . ?
C7B C8B H8B 119.6 . . ?
N1A C11A H11A 116.1 . . ?
N1A C11A C10A 127.70(14) . . ?
C10A C11A H11A 116.1 . . ?
N1B C11B H11B 116.3 . . ?
N1B C11B C10B 127.33(13) . . ?
C10B C11B H11B 116.3 . . ?
C11B C10B H10B 120.0 . . ?
C11B C10B C9B 119.93(13) . . ?
C9B C10B H10B 120.0 . . ?
C8B C9B C10B 127.66(13) . . ?
C8B C9B H9B 116.2 . . ?
C10B C9B H9B 116.2 . . ?
N1B C19B C20B 113.31(12) . . ?
N1B C19B H19A 108.9 . . ?
N1B C19B H19B 108.9 . . ?
C20B C19B H19A 108.9 . . ?
C20B C19B H19B 108.9 . . ?
H19A C19B H19B 107.7 . . ?
C18B C13B C12B 122.61(13) . . ?
C18B C13B C14B 118.62(15) . . ?
C14B C13B C12B 118.61(14) . . ?
C4A C5A H5A 119.7 . . ?
C4A C5A C6A 120.62(14) . . ?
C6A C5A H5A 119.7 . . ?
C11A C10A H10A 119.8 . . ?
C11A C10A C9A 120.43(14) . . ?
C9A C10A H10A 119.8 . . ?
N1B C12B C13B 114.65(12) . . ?
N1B C12B H12A 108.6 . . ?
N1B C12B H12B 108.6 . . ?
C13B C12B H12A 108.6 . . ?
C13B C12B H12B 108.6 . . ?
H12A C12B H12B 107.6 . . ?
C5A C4A H4A 120.2 . . ?
C5A C4A C3A 119.58(14) . . ?
C3A C4A H4A 120.2 . . ?
C14A C13A C12A 121.00(14) . . ?
C18A C13A C12A 120.17(14) . . ?
C18A C13A C14A 118.83(15) . . ?
C6B C1B H1B 119.9 . . ?
C2B C1B H1B 119.9 . . ?
C2B C1B C6B 120.18(16) . . ?
O1B C7B C8B 122.95(13) . . ?
O1B C7B C6B 118.95(13) . . ?
C8B C7B C6B 118.00(12) . . ?
C5A C6A C7A 122.06(13) . . ?
C1A C6A C5A 118.92(14) . . ?
C1A C6A C7A 118.99(13) . . ?
C10A C9A H9A 117.5 . . ?
C8A C9A C10A 125.08(15) . . ?
C8A C9A H9A 117.5 . . ?
C13B C18B H18B 119.9 . . ?
C17B C18B C13B 120.26(15) . . ?
C17B C18B H18B 119.9 . . ?
C1B C6B C7B 119.01(14) . . ?
C5B C6B C1B 118.98(14) . . ?
C5B C6B C7B 122.01(14) . . ?
C25A C20A C19A 121.49(14) . . ?
C25A C20A C21A 118.77(14) . . ?
C21A C20A C19A 119.72(13) . . ?
N1A C19A C20A 111.17(12) . . ?
N1A C19A H19C 109.4 . . ?
N1A C19A H19D 109.4 . . ?
C20A C19A H19C 109.4 . . ?
C20A C19A H19D 109.4 . . ?
H19C C19A H19D 108.0 . . ?
N1A C12A C13A 112.68(12) . . ?
N1A C12A H12C 109.1 . . ?
N1A C12A H12D 109.1 . . ?
C13A C12A H12C 109.1 . . ?
C13A C12A H12D 109.1 . . ?
H12C C12A H12D 107.8 . . ?
C9A C8A H8A 118.9 . . ?
C9A C8A C7A 122.17(14) . . ?
C7A C8A H8A 118.9 . . ?
C20B C21B H21B 119.9 . . ?
C22B C21B C20B 120.19(16) . . ?
C22B C21B H21B 119.9 . . ?
C20B C25B H25B 119.7 . . ?
C24B C25B C20B 120.55(16) . . ?
C24B C25B H25B 119.7 . . ?
O1A C7A C6A 119.00(14) . . ?
O1A C7A C8A 123.25(14) . . ?
C8A C7A C6A 117.75(13) . . ?
C13B C14B H14B 119.5 . . ?
C15B C14B C13B 120.99(16) . . ?
C15B C14B H14B 119.5 . . ?
C20A C25A H25A 119.6 . . ?
C24A C25A C20A 120.75(15) . . ?
C24A C25A H25A 119.6 . . ?
C6B C5B H5B 119.7 . . ?
C6B C5B C4B 120.54(16) . . ?
C4B C5B H5B 119.7 . . ?
C4A C3A H3A 120.0 . . ?
C2A C3A C4A 119.97(14) . . ?
C2A C3A H3A 120.0 . . ?
C6A C1A H1A 119.7 . . ?
C2A C1A C6A 120.58(15) . . ?
C2A C1A H1A 119.7 . . ?
C1B C2B H2B 119.9 . . ?
C3B C2B C1B 120.10(16) . . ?
C3B C2B H2B 119.9 . . ?
C13A C14A H14A 119.8 . . ?
C15A C14A C13A 120.45(15) . . ?
C15A C14A H14A 119.8 . . ?
C14A C15A H15A 119.9 . . ?
C16A C15A C14A 120.21(16) . . ?
C16A C15A H15A 119.9 . . ?
C13A C18A H18A 119.8 . . ?
C17A C18A C13A 120.44(16) . . ?
C17A C18A H18A 119.8 . . ?
C25A C24A H24A 120.0 . . ?
C23A C24A C25A 120.06(15) . . ?
C23A C24A H24A 120.0 . . ?
C15A C16A H16A 120.0 . . ?
C17A C16A C15A 119.91(16) . . ?
C17A C16A H16A 120.0 . . ?
C18B C17B H17B 119.7 . . ?
C16B C17B C18B 120.54(16) . . ?
C16B C17B H17B 119.7 . . ?
C14B C15B H15B 119.9 . . ?
C14B C15B C16B 120.20(16) . . ?
C16B C15B H15B 119.9 . . ?
C3A C2A C1A 120.29(15) . . ?
C3A C2A H2A 119.9 . . ?
C1A C2A H2A 119.9 . . ?
C5B C4B H4B 120.0 . . ?
C3B C4B C5B 119.99(17) . . ?
C3B C4B H4B 120.0 . . ?
C20A C21A H21A 119.8 . . ?
C22A C21A C20A 120.41(15) . . ?
C22A C21A H21A 119.8 . . ?
C17B C16B H16B 120.3 . . ?
C15B C16B C17B 119.35(16) . . ?
C15B C16B H16B 120.3 . . ?
C2B C3B H3B 119.9 . . ?
C4B C3B C2B 120.16(16) . . ?
C4B C3B H3B 119.9 . . ?
C24A C23A H23A 120.2 . . ?
C24A C23A C22A 119.68(16) . . ?
C22A C23A H23A 120.2 . . ?
C21B C22B H22B 119.7 . . ?
C23B C22B C21B 120.57(16) . . ?
C23B C22B H22B 119.7 . . ?
C25B C24B H24B 119.9 . . ?
C23B C24B C25B 120.23(16) . . ?
C23B C24B H24B 119.9 . . ?
C18A C17A H17A 119.9 . . ?
C16A C17A C18A 120.14(15) . . ?
C16A C17A H17A 119.9 . . ?
C22B C23B H23B 120.2 . . ?
C24B C23B C22B 119.58(16) . . ?
C24B C23B H23B 120.2 . . ?
C21A C22A C23A 120.31(17) . . ?
C21A C22A H22A 119.8 . . ?
C23A C22A H22A 119.8 . . ?

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
O1B C7B C6B C1B 31.4(2) . . . . ?
O1B C7B C6B C5B -148.68(15) . . . . ?
N1B C11B C10B C9B 179.72(13) . . . . ?
N1A C11A C10A C9A -176.14(13) . . . . ?
C20B C21B C22B C23B 1.9(2) . . . . ?
C20B C25B C24B C23B 1.8(2) . . . . ?
C8B C7B C6B C1B -145.26(14) . . . . ?
C8B C7B C6B C5B 34.7(2) . . . . ?
C11A N1A C19A C20A 112.38(15) . . . . ?
C11A N1A C12A C13A 107.55(15) . . . . ?
C11A C10A C9A C8A 174.87(14) . . . . ?
C11B N1B C19B C20B 106.45(15) . . . . ?
C11B N1B C12B C13B 87.50(16) . . . . ?
C11B C10B C9B C8B 178.95(14) . . . . ?
C9B C8B C7B O1B -6.1(2) . . . . ?
C9B C8B C7B C6B 170.36(13) . . . . ?
C19B N1B C11B C10B -178.00(14) . . . . ?
C19B N1B C12B C13B -96.28(15) . . . . ?
C19B C20B C21B C22B -177.88(14) . . . . ?
C19B C20B C25B C24B 176.11(14) . . . . ?
C13B C18B C17B C16B 0.3(2) . . . . ?
C13B C14B C15B C16B -0.8(2) . . . . ?
C5A C4A C3A C2A 2.0(2) . . . . ?
C5A C6A C7A O1A 152.10(14) . . . . ?
C5A C6A C7A C8A -27.5(2) . . . . ?
C5A C6A C1A C2A 2.1(2) . . . . ?
C10A C9A C8A C7A -175.80(14) . . . . ?
C12B N1B C11B C10B -1.9(2) . . . . ?
C12B N1B C19B C20B -69.76(16) . . . . ?
C12B C13B C18B C17B 173.48(14) . . . . ?
C12B C13B C14B C15B -173.39(14) . . . . ?
C4A C5A C6A C7A -178.99(13) . . . . ?
C4A C5A C6A C1A -1.2(2) . . . . ?
C4A C3A C2A C1A -1.1(3) . . . . ?
C13A C14A C15A C16A -0.7(2) . . . . ?
C13A C18A C17A C16A -0.3(2) . . . . ?
C1B C6B C5B C4B -0.1(2) . . . . ?
C1B C2B C3B C4B -0.2(2) . . . . ?
C7B C8B C9B C10B -172.58(14) . . . . ?
C7B C6B C5B C4B 179.98(14) . . . . ?
C6A C5A C4A C3A -0.9(2) . . . . ?
C6A C1A C2A C3A -1.0(3) . . . . ?
C9A C8A C7A O1A -9.0(2) . . . . ?
C9A C8A C7A C6A 170.53(13) . . . . ?
C18B C13B C12B N1B 25.84(19) . . . . ?
C18B C13B C14B C15B 2.2(2) . . . . ?
C18B C17B C16B C15B 1.0(2) . . . . ?
C6B C1B C2B C3B 1.7(2) . . . . ?
C6B C5B C4B C3B 1.7(2) . . . . ?
C20A C25A C24A C23A 0.6(2) . . . . ?
C20A C21A C22A C23A 0.8(3) . . . . ?
C19A N1A C11A C10A 177.51(14) . . . . ?
C19A N1A C12A C13A -73.50(15) . . . . ?
C19A C20A C25A C24A -179.10(14) . . . . ?
C19A C20A C21A C22A 178.41(16) . . . . ?
C12A N1A C11A C10A -3.6(2) . . . . ?
C12A N1A C19A C20A -66.59(16) . . . . ?
C12A C13A C14A C15A -179.13(14) . . . . ?
C12A C13A C18A C17A 179.63(14) . . . . ?
C21B C20B C19B N1B -32.53(19) . . . . ?
C21B C20B C25B C24B -1.7(2) . . . . ?
C21B C22B C23B C24B -1.8(3) . . . . ?
C25B C20B C19B N1B 149.74(13) . . . . ?
C25B C20B C21B C22B -0.1(2) . . . . ?
C25B C24B C23B C22B -0.1(3) . . . . ?
C7A C6A C1A C2A 180.00(15) . . . . ?
C14B C13B C12B N1B -158.78(12) . . . . ?
C14B C13B C18B C17B -1.9(2) . . . . ?
C14B C15B C16B C17B -0.8(3) . . . . ?
C25A C20A C19A N1A 108.66(16) . . . . ?
C25A C20A C21A C22A 0.3(2) . . . . ?
C25A C24A C23A C22A 0.4(3) . . . . ?
C5B C4B C3B C2B -1.5(3) . . . . ?
C1A C6A C7A O1A -25.7(2) . . . . ?
C1A C6A C7A C8A 154.71(14) . . . . ?
C2B C1B C6B C7B 178.33(13) . . . . ?
C2B C1B C6B C5B -1.6(2) . . . . ?
C14A C13A C12A N1A -52.13(18) . . . . ?
C14A C13A C18A C17A -0.5(2) . . . . ?
C14A C15A C16A C17A -0.1(3) . . . . ?
C15A C16A C17A C18A 0.6(3) . . . . ?
C18A C13A C12A N1A 127.74(14) . . . . ?
C18A C13A C14A C15A 1.0(2) . . . . ?
C24A C23A C22A C21A -1.2(3) . . . . ?
C21A C20A C19A N1A -69.44(18) . . . . ?
C21A C20A C25A C24A -1.0(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 1.364
_oxdiff_exptl_absorpt_empirical_full_min 0.790
