# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
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data_wx-02-r21-1-2f
_database_code_depnum_ccdc_archive 'CCDC 2300788'
loop_
_audit_author_name
_audit_author_address
'Xuan Wang'
;Guangdong Provincial Hospital of Chinese Medicine,
China
;
_audit_update_record             
;
2023-10-12 deposited with the CCDC.	2024-01-18 downloaded from the CCDC.
;
_audit_creation_date             2023-05-25
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H13 F2 N O'
_chemical_formula_sum            'C16 H13 F2 N O'
_chemical_formula_weight         273.27
_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      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                   10.1690(2)
_cell_length_b                   10.8560(2)
_cell_length_c                   12.0502(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.790(2)
_cell_angle_gamma                90
_cell_volume                     1297.27(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3381
_cell_measurement_temperature    170.00(18)
_cell_measurement_theta_max      73.4180
_cell_measurement_theta_min      3.9880
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.900
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65603
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4569
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.710
_diffrn_reflns_theta_min         5.160
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(18)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00  31.00   1.00    1.00    --  -40.92  37.00  30.00   96
  2  ω     50.00  80.00   1.00    1.00    --   40.92 -99.00 120.00   30
  3  ω     42.00 107.00   1.00    1.00    --  107.58 -45.00 150.00   65
  4  ω     89.00 144.00   1.00    1.00    --  107.58  30.00   0.00   55
  5  ω     96.00 122.00   1.00    1.00    --  107.58  30.00-120.00   26
  6  ω    130.00 176.00   1.00    1.00    --  107.58  30.00-120.00   46
  7  ω     48.00 106.00   1.00    1.00    --  107.58 -94.00 -30.00   58
  8  ω     34.00  76.00   1.00    1.00    --  107.58 -30.00-120.00   42
  9  ω     35.00 136.00   1.00    1.00    --  107.58 -61.00 -30.00  101
 10  ω    -95.00 -69.00   1.00    1.00    --  -40.92-140.00 122.00   26
 11  ω   -100.00 -20.00   1.00    1.00    --  -40.92 -37.00  30.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0981363000
_diffrn_orient_matrix_UB_12      0.0191017000
_diffrn_orient_matrix_UB_13      0.1158875000
_diffrn_orient_matrix_UB_21      0.1155943000
_diffrn_orient_matrix_UB_22      0.0241182000
_diffrn_orient_matrix_UB_23      -0.0610226000
_diffrn_orient_matrix_UB_31      -0.0335840000
_diffrn_orient_matrix_UB_32      0.1385792000
_diffrn_orient_matrix_UB_33      -0.0054613000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2282
_reflns_number_total             2541
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0193(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2541
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.047
_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)+(0.0539P)²+0.3043P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1028
_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 Ternary CH refined with riding coordinates:
 C8(H8), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), 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 0.60182(8) 0.34734(9) 0.68395(7) 0.0437(3) Uani 1 1 d . . . . .
F2 F 0.16668(9) 0.39506(11) 0.45345(8) 0.0522(3) Uani 1 1 d . . . . .
O1 O 0.14460(9) 0.35001(9) 0.68697(8) 0.0313(2) Uani 1 1 d . . . . .
N1 N 0.28486(10) 0.34500(10) 0.74414(9) 0.0253(3) Uani 1 1 d . . . . .
C1 C 0.20277(14) 0.47070(12) 0.88742(12) 0.0327(3) Uani 1 1 d . . . . .
C2 C 0.21810(17) 0.50448(14) 1.00065(14) 0.0429(4) Uani 1 1 d . . . . .
H2 H 0.156254 0.560993 1.021240 0.051 Uiso 1 1 calc R U . . .
C3 C 0.32183(18) 0.45736(16) 1.08416(14) 0.0477(4) Uani 1 1 d . . . . .
H3 H 0.330238 0.481409 1.161216 0.057 Uiso 1 1 calc R U . . .
C4 C 0.41305(17) 0.37560(16) 1.05589(13) 0.0429(4) Uani 1 1 d . . . . .
H4 H 0.484608 0.343932 1.113229 0.051 Uiso 1 1 calc R U . . .
C5 C 0.39988(14) 0.33982(13) 0.94350(13) 0.0333(3) Uani 1 1 d . . . . .
H5 H 0.462214 0.283339 0.923597 0.040 Uiso 1 1 calc R U . . .
C6 C 0.29515(13) 0.38689(11) 0.86006(11) 0.0269(3) Uani 1 1 d . . . . .
C7 C 0.09051(15) 0.52039(14) 0.79481(14) 0.0398(4) Uani 1 1 d . . . . .
H7A H 0.088627 0.611421 0.799047 0.048 Uiso 1 1 calc R U . . .
H7B H 0.002715 0.488599 0.805043 0.048 Uiso 1 1 calc R U . . .
C8 C 0.11323(14) 0.48079(14) 0.67998(13) 0.0358(3) Uani 1 1 d . . . . .
H8 H 0.031736 0.497726 0.618317 0.043 Uiso 1 1 calc R U . . .
C9 C 0.23904(14) 0.54082(13) 0.65307(13) 0.0356(3) Uani 1 1 d . . . . .
H9A H 0.267709 0.613371 0.702261 0.043 Uiso 1 1 calc R U . . .
H9B H 0.222600 0.566572 0.572359 0.043 Uiso 1 1 calc R U . . .
C10 C 0.34527(12) 0.43715(12) 0.67862(11) 0.0267(3) Uani 1 1 d . . . . .
H10 H 0.429055 0.470823 0.729083 0.032 Uiso 1 1 calc R U . . .
C11 C 0.38220(12) 0.37853(11) 0.57583(11) 0.0262(3) Uani 1 1 d . . . . .
C12 C 0.51348(13) 0.33769(12) 0.58200(12) 0.0287(3) Uani 1 1 d . . . . .
C13 C 0.56006(14) 0.28843(13) 0.49279(13) 0.0349(3) Uani 1 1 d . . . . .
H13 H 0.650865 0.261628 0.502876 0.042 Uiso 1 1 calc R U . . .
C14 C 0.47199(15) 0.27894(13) 0.38866(13) 0.0370(3) Uani 1 1 d . . . . .
H14 H 0.502558 0.247654 0.325173 0.044 Uiso 1 1 calc R U . . .
C15 C 0.33890(16) 0.31485(15) 0.37606(13) 0.0384(3) Uani 1 1 d . . . . .
H15 H 0.276842 0.306844 0.304846 0.046 Uiso 1 1 calc R U . . .
C16 C 0.29846(13) 0.36243(13) 0.46906(12) 0.0326(3) 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
F1 C12 1.3560(15) . ?
F2 C16 1.3584(16) . ?
O1 N1 1.4411(14) . ?
O1 C8 1.4535(17) . ?
N1 C6 1.4507(17) . ?
N1 C10 1.4887(16) . ?
C1 C2 1.388(2) . ?
C1 C6 1.3986(18) . ?
C1 C7 1.508(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.380(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.387(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.3900(19) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.515(2) . ?
C8 H8 1.0000 . ?
C8 C9 1.5331(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5431(17) . ?
C10 H10 1.0000 . ?
C10 C11 1.5120(18) . ?
C11 C12 1.3930(18) . ?
C11 C16 1.3878(19) . ?
C12 C13 1.375(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.375(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.384(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.377(2) . ?

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
N1 O1 C8 104.24(9) . . ?
O1 N1 C6 107.53(9) . . ?
O1 N1 C10 101.66(9) . . ?
C6 N1 C10 110.47(10) . . ?
C2 C1 C6 117.94(14) . . ?
C2 C1 C7 122.32(14) . . ?
C6 C1 C7 119.74(13) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.23(15) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.25(15) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.77(15) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.76(14) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 N1 121.46(12) . . ?
C5 C6 N1 117.49(12) . . ?
C5 C6 C1 121.05(13) . . ?
C1 C7 H7A 109.8 . . ?
C1 C7 H7B 109.8 . . ?
C1 C7 C8 109.32(11) . . ?
H7A C7 H7B 108.3 . . ?
C8 C7 H7A 109.8 . . ?
C8 C7 H7B 109.8 . . ?
O1 C8 C7 107.46(11) . . ?
O1 C8 H8 111.0 . . ?
O1 C8 C9 104.16(10) . . ?
C7 C8 H8 111.0 . . ?
C7 C8 C9 112.07(13) . . ?
C9 C8 H8 111.0 . . ?
C8 C9 H9A 111.1 . . ?
C8 C9 H9B 111.1 . . ?
C8 C9 C10 103.17(11) . . ?
H9A C9 H9B 109.1 . . ?
C10 C9 H9A 111.1 . . ?
C10 C9 H9B 111.1 . . ?
N1 C10 C9 104.07(10) . . ?
N1 C10 H10 108.6 . . ?
N1 C10 C11 110.98(10) . . ?
C9 C10 H10 108.6 . . ?
C11 C10 C9 115.68(11) . . ?
C11 C10 H10 108.6 . . ?
C12 C11 C10 119.94(12) . . ?
C16 C11 C10 126.85(11) . . ?
C16 C11 C12 113.17(12) . . ?
F1 C12 C11 117.30(12) . . ?
F1 C12 C13 117.68(12) . . ?
C13 C12 C11 125.02(13) . . ?
C12 C13 H13 120.8 . . ?
C14 C13 C12 118.37(13) . . ?
C14 C13 H13 120.8 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.17(13) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.7 . . ?
C16 C15 C14 118.51(14) . . ?
C16 C15 H15 120.7 . . ?
F2 C16 C11 118.66(12) . . ?
F2 C16 C15 116.64(13) . . ?
C15 C16 C11 124.70(13) . . ?

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
F1 C12 C13 C14 -179.50(12) . . . . ?
O1 N1 C6 C1 -28.56(15) . . . . ?
O1 N1 C6 C5 150.93(11) . . . . ?
O1 N1 C10 C9 38.15(12) . . . . ?
O1 N1 C10 C11 -86.93(11) . . . . ?
O1 C8 C9 C10 -14.32(14) . . . . ?
N1 O1 C8 C7 -79.73(12) . . . . ?
N1 O1 C8 C9 39.33(13) . . . . ?
N1 C10 C11 C12 -95.83(14) . . . . ?
N1 C10 C11 C16 86.29(16) . . . . ?
C1 C2 C3 C4 0.3(2) . . . . ?
C1 C7 C8 O1 47.17(15) . . . . ?
C1 C7 C8 C9 -66.68(15) . . . . ?
C2 C1 C6 N1 178.83(12) . . . . ?
C2 C1 C6 C5 -0.6(2) . . . . ?
C2 C1 C7 C8 171.90(13) . . . . ?
C2 C3 C4 C5 -0.6(2) . . . . ?
C3 C4 C5 C6 0.2(2) . . . . ?
C4 C5 C6 N1 -179.10(12) . . . . ?
C4 C5 C6 C1 0.4(2) . . . . ?
C6 N1 C10 C9 -75.76(13) . . . . ?
C6 N1 C10 C11 159.16(10) . . . . ?
C6 C1 C2 C3 0.3(2) . . . . ?
C6 C1 C7 C8 -8.56(19) . . . . ?
C7 C1 C2 C3 179.85(14) . . . . ?
C7 C1 C6 N1 -0.73(19) . . . . ?
C7 C1 C6 C5 179.80(13) . . . . ?
C7 C8 C9 C10 101.55(13) . . . . ?
C8 O1 N1 C6 67.32(11) . . . . ?
C8 O1 N1 C10 -48.76(11) . . . . ?
C8 C9 C10 N1 -14.38(14) . . . . ?
C8 C9 C10 C11 107.64(13) . . . . ?
C9 C10 C11 C12 145.91(12) . . . . ?
C9 C10 C11 C16 -31.96(19) . . . . ?
C10 N1 C6 C1 81.57(14) . . . . ?
C10 N1 C6 C5 -98.94(13) . . . . ?
C10 C11 C12 F1 3.24(18) . . . . ?
C10 C11 C12 C13 -176.80(13) . . . . ?
C10 C11 C16 F2 -4.1(2) . . . . ?
C10 C11 C16 C15 176.06(13) . . . . ?
C11 C12 C13 C14 0.5(2) . . . . ?
C12 C11 C16 F2 177.87(12) . . . . ?
C12 C11 C16 C15 -1.9(2) . . . . ?
C12 C13 C14 C15 -2.0(2) . . . . ?
C13 C14 C15 C16 1.5(2) . . . . ?
C14 C15 C16 F2 -179.18(13) . . . . ?
C14 C15 C16 C11 0.6(2) . . . . ?
C16 C11 C12 F1 -178.61(12) . . . . ?
C16 C11 C12 C13 1.3(2) . . . . ?

_olex2_date_sample_data_collection 2023-05-25
_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 1.307
_oxdiff_exptl_absorpt_empirical_full_min 0.734
####################################################################### 
# 
# 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_ljl-39-2
_database_code_depnum_ccdc_archive 'CCDC 2300790'
loop_
_audit_author_name
_audit_author_address
'Xuan Wang'
;Guangdong Provincial Hospital of Chinese Medicine,
China
;
_audit_update_record             
;
2023-10-12 deposited with the CCDC.	2024-01-18 downloaded from the CCDC.
;
_audit_creation_date             2023-09-26
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H13 F2 N O'
_chemical_formula_sum            'C16 H13 F2 N O'
_chemical_formula_weight         273.27
_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      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                   9.7065(3)
_cell_length_b                   11.7198(4)
_cell_length_c                   12.0290(4)
_cell_angle_alpha                77.710(3)
_cell_angle_beta                 89.322(3)
_cell_angle_gamma                71.433(3)
_cell_volume                     1265.13(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6079
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      73.4040
_cell_measurement_theta_min      3.7390
_shelx_estimated_absorpt_T_max   0.897
_shelx_estimated_absorpt_T_min   0.859
_exptl_absorpt_coefficient_mu    0.923
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8430
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.544
_diffrn_reflns_theta_min         3.768
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00  33.00   1.00    1.00    --  -40.73  38.00 -90.00   93
  2  ω      5.00  34.00   1.00    1.00    --   40.73 -99.00-180.00   29
  3  ω     60.00  90.00   1.00    1.00    --   40.73-125.00 -90.00   30
  4  ω     90.00 116.00   1.00    1.00    --  106.95-125.00 -30.00   26
  5  ω     94.00 133.00   1.00    1.00    --  106.95 -45.00  90.00   39
  6  ω     89.00 172.00   1.00    1.00    --  106.95  30.00  90.00   83
  7  ω    127.00 173.00   1.00    1.00    --  106.95  61.00  30.00   46
  8  ω     95.00 122.00   1.00    1.00    --  106.95 125.00 -30.00   27
  9  ω     78.00 123.00   1.00    1.00    --  106.95  61.00  30.00   45
 10  ω     75.00 132.00   1.00    1.00    --  106.95  77.00 -60.00   57
 11  ω     81.00 171.00   1.00    1.00    --  106.95  45.00 150.00   90
 12  ω     41.00  67.00   1.00    1.00    --  106.95-125.00 -30.00   26
 13  ω     33.00 138.00   1.00    1.00    --  106.95 -77.00 -30.00  105
 14  ω     36.00 105.00   1.00    1.00    --  106.95 -77.00-120.00   69
 15  ω     27.00 102.00   1.00    1.00    --  106.95 -94.00-180.00   75
 16  ω     34.00 121.00   1.00    1.00    --  106.95-125.00 150.00   87
 17  ω    -69.00  25.00   1.00    1.00    --  -40.73  57.00 120.00   94
 18  ω   -113.00 -22.00   1.00    1.00    --  -40.73 -57.00 -30.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1232963000
_diffrn_orient_matrix_UB_12      0.0068301000
_diffrn_orient_matrix_UB_13      -0.0831916000
_diffrn_orient_matrix_UB_21      -0.1130510000
_diffrn_orient_matrix_UB_22      0.0740049000
_diffrn_orient_matrix_UB_23      0.0710191000
_diffrn_orient_matrix_UB_31      0.0123592000
_diffrn_orient_matrix_UB_32      0.1211974000
_diffrn_orient_matrix_UB_33      -0.0726565000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4444
_reflns_number_total             4941
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.121
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         4941
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0517
_refine_ls_restrained_S_all      1.059
_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)+(0.0880P)²+0.2445P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1391
_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 Ternary CH refined with riding coordinates:
 C7(H7), C9(H9), C24(H24), C26(H26)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C23(H23A,H23B), C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C13(H13), C14(H14), C20(H20),
 C21(H21), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32)
;
_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 1.11903(11) 0.49854(9) 0.86069(10) 0.0442(3) Uani 1 1 d . . . . .
F2 F 1.32563(11) 0.49671(9) 1.00750(10) 0.0431(3) Uani 1 1 d . . . . .
O1 O 0.70018(11) 0.84982(10) 0.88645(10) 0.0295(3) Uani 1 1 d . . . . .
N1 N 0.81343(12) 0.89294(11) 0.92046(10) 0.0223(3) Uani 1 1 d . . . . .
C1 C 0.69218(14) 1.10811(13) 0.81621(12) 0.0209(3) Uani 1 1 d . . . . .
C2 C 0.67188(16) 1.20473(13) 0.72097(13) 0.0245(3) Uani 1 1 d . . . . .
H2 H 0.734773 1.194197 0.660183 0.029 Uiso 1 1 calc R U . . .
C3 C 0.56135(16) 1.31582(14) 0.71372(13) 0.0280(3) Uani 1 1 d . . . . .
H3 H 0.548678 1.380536 0.648031 0.034 Uiso 1 1 calc R U . . .
C4 C 0.46917(16) 1.33293(14) 0.80191(14) 0.0293(3) Uani 1 1 d . . . . .
H4 H 0.393636 1.409243 0.797194 0.035 Uiso 1 1 calc R U . . .
C5 C 0.48820(16) 1.23767(15) 0.89702(14) 0.0293(3) Uani 1 1 d . . . . .
H5 H 0.425191 1.248787 0.957674 0.035 Uiso 1 1 calc R U . . .
C6 C 0.59890(16) 1.12586(14) 0.90439(13) 0.0253(3) Uani 1 1 d . . . . .
H6 H 0.610937 1.061182 0.970016 0.030 Uiso 1 1 calc R U . . .
C7 C 0.81438(14) 0.98836(13) 0.81857(12) 0.0214(3) Uani 1 1 d . . . . .
H7 H 0.910149 1.003560 0.817145 0.026 Uiso 1 1 calc R U . . .
C8 C 0.79916(18) 0.92744(14) 0.71952(13) 0.0305(3) Uani 1 1 d . . . . .
H8A H 0.730345 0.987062 0.657744 0.037 Uiso 1 1 calc R U . . .
H8B H 0.894544 0.893924 0.687865 0.037 Uiso 1 1 calc R U . . .
C9 C 0.74011(17) 0.82377(15) 0.77584(15) 0.0319(4) Uani 1 1 d . . . . .
H9 H 0.653226 0.826053 0.730482 0.038 Uiso 1 1 calc R U . . .
C10 C 0.85439(17) 0.69637(14) 0.79728(15) 0.0325(4) Uani 1 1 d . . . . .
H10A H 0.809057 0.632148 0.826894 0.039 Uiso 1 1 calc R U . . .
H10B H 0.899582 0.680652 0.725454 0.039 Uiso 1 1 calc R U . . .
C11 C 0.96783(16) 0.69313(13) 0.88345(13) 0.0246(3) Uani 1 1 d . . . . .
C12 C 0.94832(15) 0.79091(13) 0.93809(12) 0.0228(3) Uani 1 1 d . . . . .
C13 C 1.05650(17) 0.79200(14) 1.01156(13) 0.0291(3) Uani 1 1 d . . . . .
H13 H 1.042420 0.860423 1.045917 0.035 Uiso 1 1 calc R U . . .
C14 C 1.18529(18) 0.69362(15) 1.03517(14) 0.0323(4) Uani 1 1 d . . . . .
H14 H 1.260095 0.694222 1.085040 0.039 Uiso 1 1 calc R U . . .
C15 C 1.20278(16) 0.59507(14) 0.98504(14) 0.0296(3) Uani 1 1 d . . . . .
C16 C 1.09614(17) 0.59534(14) 0.91020(14) 0.0282(3) Uani 1 1 d . . . . .
F3 F 1.25982(12) 0.49260(9) 0.57100(10) 0.0470(3) Uani 1 1 d . . . . .
F4 F 1.09828(11) 0.50465(8) 0.38770(10) 0.0418(3) Uani 1 1 d . . . . .
O4 O 0.87419(11) 0.93781(9) 0.22506(8) 0.0246(2) Uani 1 1 d . . . . .
N2 N 0.88137(12) 0.94461(11) 0.34365(10) 0.0210(3) Uani 1 1 d . . . . .
C17 C 0.98197(15) 0.71865(13) 0.36643(13) 0.0240(3) Uani 1 1 d . . . . .
C18 C 1.08212(17) 0.60926(13) 0.42428(14) 0.0295(3) Uani 1 1 d . . . . .
C19 C 1.16481(16) 0.60325(14) 0.51864(15) 0.0310(3) Uani 1 1 d . . . . .
C20 C 1.15204(16) 0.70700(15) 0.55950(14) 0.0292(3) Uani 1 1 d . . . . .
H20 H 1.207454 0.701991 0.625987 0.035 Uiso 1 1 calc R U . . .
C21 C 1.05631(15) 0.81919(13) 0.50133(13) 0.0246(3) Uani 1 1 d . . . . .
H21 H 1.047425 0.892326 0.527011 0.029 Uiso 1 1 calc R U . . .
C22 C 0.97349(14) 0.82485(13) 0.40572(12) 0.0215(3) Uani 1 1 d . . . . .
C23 C 0.88929(17) 0.72414(14) 0.26534(13) 0.0281(3) Uani 1 1 d . . . . .
H23A H 0.830406 0.668605 0.287271 0.034 Uiso 1 1 calc R U . . .
H23B H 0.951944 0.696506 0.204246 0.034 Uiso 1 1 calc R U . . .
C24 C 0.78971(16) 0.85583(14) 0.22235(13) 0.0262(3) Uani 1 1 d . . . . .
H24 H 0.749208 0.867460 0.143161 0.031 Uiso 1 1 calc R U . . .
C25 C 0.66672(16) 0.89768(14) 0.30077(14) 0.0287(3) Uani 1 1 d . . . . .
H25A H 0.646915 0.825938 0.349708 0.034 Uiso 1 1 calc R U . . .
H25B H 0.576130 0.952329 0.255903 0.034 Uiso 1 1 calc R U . . .
C26 C 0.72608(14) 0.96842(13) 0.37322(12) 0.0216(3) Uani 1 1 d . . . . .
H26 H 0.722854 0.931952 0.455914 0.026 Uiso 1 1 calc R U . . .
C27 C 0.64274(14) 1.10538(13) 0.34901(12) 0.0227(3) Uani 1 1 d . . . . .
C28 C 0.64202(17) 1.18296(15) 0.24351(14) 0.0306(3) Uani 1 1 d . . . . .
H28 H 0.700153 1.151078 0.186031 0.037 Uiso 1 1 calc R U . . .
C29 C 0.55695(18) 1.30654(15) 0.22171(15) 0.0354(4) Uani 1 1 d . . . . .
H29 H 0.557715 1.358740 0.149661 0.043 Uiso 1 1 calc R U . . .
C30 C 0.47085(17) 1.35411(14) 0.30471(16) 0.0348(4) Uani 1 1 d . . . . .
H30 H 0.411689 1.438354 0.289227 0.042 Uiso 1 1 calc R U . . .
C31 C 0.47160(17) 1.27842(15) 0.40984(15) 0.0330(4) Uani 1 1 d . . . . .
H31 H 0.413757 1.310790 0.467229 0.040 Uiso 1 1 calc R U . . .
C32 C 0.55711(16) 1.15461(14) 0.43181(13) 0.0271(3) Uani 1 1 d . . . . .
H32 H 0.556980 1.103060 0.504351 0.032 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 C16 1.3473(17) . ?
F2 C15 1.3504(17) . ?
O1 N1 1.4435(15) . ?
O1 C9 1.449(2) . ?
N1 C7 1.4750(17) . ?
N1 C12 1.4459(17) . ?
C1 C2 1.395(2) . ?
C1 C6 1.393(2) . ?
C1 C7 1.5169(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(2) . ?
C6 H6 0.9500 . ?
C7 H7 1.0000 . ?
C7 C8 1.544(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.532(2) . ?
C9 H9 1.0000 . ?
C9 C10 1.521(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.507(2) . ?
C11 C12 1.400(2) . ?
C11 C16 1.383(2) . ?
C12 C13 1.385(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.377(2) . ?
C15 C16 1.379(2) . ?
F3 C19 1.3540(17) . ?
F4 C18 1.3516(18) . ?
O4 N2 1.4492(15) . ?
O4 C24 1.4534(17) . ?
N2 C22 1.4482(17) . ?
N2 C26 1.4961(17) . ?
C17 C18 1.384(2) . ?
C17 C22 1.401(2) . ?
C17 C23 1.499(2) . ?
C18 C19 1.374(2) . ?
C19 C20 1.376(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.388(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.389(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.518(2) . ?
C24 H24 1.0000 . ?
C24 C25 1.534(2) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.550(2) . ?
C26 H26 1.0000 . ?
C26 C27 1.5151(19) . ?
C27 C28 1.394(2) . ?
C27 C32 1.391(2) . ?
C28 H28 0.9500 . ?
C28 C29 1.389(2) . ?
C29 H29 0.9500 . ?
C29 C30 1.388(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.380(3) . ?
C31 H31 0.9500 . ?
C31 C32 1.392(2) . ?
C32 H32 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
N1 O1 C9 103.89(10) . . ?
O1 N1 C7 101.28(10) . . ?
O1 N1 C12 107.91(10) . . ?
C12 N1 C7 111.42(11) . . ?
C2 C1 C7 118.42(12) . . ?
C6 C1 C2 118.48(13) . . ?
C6 C1 C7 123.10(12) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 120.95(14) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.25(14) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.37(14) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.50(14) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.45(14) . . ?
C5 C6 H6 119.8 . . ?
N1 C7 C1 111.48(11) . . ?
N1 C7 H7 109.7 . . ?
N1 C7 C8 102.95(11) . . ?
C1 C7 H7 109.7 . . ?
C1 C7 C8 113.24(12) . . ?
C8 C7 H7 109.7 . . ?
C7 C8 H8A 111.1 . . ?
C7 C8 H8B 111.1 . . ?
H8A C8 H8B 109.1 . . ?
C9 C8 C7 103.30(12) . . ?
C9 C8 H8A 111.1 . . ?
C9 C8 H8B 111.1 . . ?
O1 C9 C8 103.94(12) . . ?
O1 C9 H9 110.8 . . ?
O1 C9 C10 106.89(13) . . ?
C8 C9 H9 110.8 . . ?
C10 C9 C8 113.29(13) . . ?
C10 C9 H9 110.8 . . ?
C9 C10 H10A 110.2 . . ?
C9 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
C11 C10 C9 107.61(12) . . ?
C11 C10 H10A 110.2 . . ?
C11 C10 H10B 110.2 . . ?
C12 C11 C10 121.00(13) . . ?
C16 C11 C10 121.71(14) . . ?
C16 C11 C12 117.27(14) . . ?
C11 C12 N1 120.74(13) . . ?
C13 C12 N1 118.13(13) . . ?
C13 C12 C11 121.12(13) . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.28(14) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.6 . . ?
C15 C14 C13 118.81(14) . . ?
C15 C14 H14 120.6 . . ?
F2 C15 C14 120.50(14) . . ?
F2 C15 C16 118.73(14) . . ?
C14 C15 C16 120.77(14) . . ?
F1 C16 C11 119.38(14) . . ?
F1 C16 C15 118.94(14) . . ?
C15 C16 C11 121.67(14) . . ?
N2 O4 C24 104.54(10) . . ?
O4 N2 C26 102.20(10) . . ?
C22 N2 O4 106.87(10) . . ?
C22 N2 C26 111.44(10) . . ?
C18 C17 C22 116.59(14) . . ?
C18 C17 C23 121.88(14) . . ?
C22 C17 C23 121.52(13) . . ?
F4 C18 C17 119.08(15) . . ?
F4 C18 C19 118.83(14) . . ?
C19 C18 C17 122.08(14) . . ?
F3 C19 C18 118.56(15) . . ?
F3 C19 C20 120.37(15) . . ?
C18 C19 C20 121.07(14) . . ?
C19 C20 H20 120.8 . . ?
C19 C20 C21 118.47(15) . . ?
C21 C20 H20 120.8 . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C22 120.21(14) . . ?
C22 C21 H21 119.9 . . ?
C17 C22 N2 120.04(13) . . ?
C21 C22 N2 118.43(12) . . ?
C21 C22 C17 121.49(13) . . ?
C17 C23 H23A 109.8 . . ?
C17 C23 H23B 109.8 . . ?
C17 C23 C24 109.20(12) . . ?
H23A C23 H23B 108.3 . . ?
C24 C23 H23A 109.8 . . ?
C24 C23 H23B 109.8 . . ?
O4 C24 C23 107.95(12) . . ?
O4 C24 H24 110.6 . . ?
O4 C24 C25 103.20(11) . . ?
C23 C24 H24 110.6 . . ?
C23 C24 C25 113.75(13) . . ?
C25 C24 H24 110.6 . . ?
C24 C25 H25A 111.0 . . ?
C24 C25 H25B 111.0 . . ?
C24 C25 C26 103.81(11) . . ?
H25A C25 H25B 109.0 . . ?
C26 C25 H25A 111.0 . . ?
C26 C25 H25B 111.0 . . ?
N2 C26 C25 104.30(11) . . ?
N2 C26 H26 109.2 . . ?
N2 C26 C27 111.41(11) . . ?
C25 C26 H26 109.2 . . ?
C27 C26 C25 113.28(12) . . ?
C27 C26 H26 109.2 . . ?
C28 C27 C26 122.00(13) . . ?
C32 C27 C26 119.35(13) . . ?
C32 C27 C28 118.53(14) . . ?
C27 C28 H28 119.7 . . ?
C29 C28 C27 120.53(15) . . ?
C29 C28 H28 119.7 . . ?
C28 C29 H29 119.8 . . ?
C30 C29 C28 120.31(15) . . ?
C30 C29 H29 119.8 . . ?
C29 C30 H30 120.2 . . ?
C31 C30 C29 119.68(14) . . ?
C31 C30 H30 120.2 . . ?
C30 C31 H31 120.0 . . ?
C30 C31 C32 120.02(15) . . ?
C32 C31 H31 120.0 . . ?
C27 C32 C31 120.92(15) . . ?
C27 C32 H32 119.5 . . ?
C31 C32 H32 119.5 . . ?

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
F2 C15 C16 F1 -1.0(2) . . . . ?
F2 C15 C16 C11 -179.97(14) . . . . ?
O1 N1 C7 C1 79.92(12) . . . . ?
O1 N1 C7 C8 -41.79(12) . . . . ?
O1 N1 C12 C11 24.33(16) . . . . ?
O1 N1 C12 C13 -154.82(13) . . . . ?
O1 C9 C10 C11 -48.73(16) . . . . ?
N1 O1 C9 C8 -38.13(13) . . . . ?
N1 O1 C9 C10 81.94(13) . . . . ?
N1 C7 C8 C9 18.56(14) . . . . ?
N1 C12 C13 C14 177.13(14) . . . . ?
C1 C2 C3 C4 0.4(2) . . . . ?
C1 C7 C8 C9 -101.95(13) . . . . ?
C2 C1 C6 C5 0.0(2) . . . . ?
C2 C1 C7 N1 -175.42(12) . . . . ?
C2 C1 C7 C8 -59.88(17) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
C3 C4 C5 C6 0.2(2) . . . . ?
C4 C5 C6 C1 0.0(2) . . . . ?
C6 C1 C2 C3 -0.2(2) . . . . ?
C6 C1 C7 N1 4.24(19) . . . . ?
C6 C1 C7 C8 119.78(15) . . . . ?
C7 N1 C12 C11 -86.01(15) . . . . ?
C7 N1 C12 C13 94.84(15) . . . . ?
C7 C1 C2 C3 179.48(13) . . . . ?
C7 C1 C6 C5 -179.64(13) . . . . ?
C7 C8 C9 O1 11.23(14) . . . . ?
C7 C8 C9 C10 -104.42(14) . . . . ?
C8 C9 C10 C11 65.15(17) . . . . ?
C9 O1 N1 C7 50.74(12) . . . . ?
C9 O1 N1 C12 -66.37(13) . . . . ?
C9 C10 C11 C12 7.1(2) . . . . ?
C9 C10 C11 C16 -171.57(15) . . . . ?
C10 C11 C12 N1 5.2(2) . . . . ?
C10 C11 C12 C13 -175.64(14) . . . . ?
C10 C11 C16 F1 -2.0(2) . . . . ?
C10 C11 C16 C15 176.93(15) . . . . ?
C11 C12 C13 C14 -2.0(2) . . . . ?
C12 N1 C7 C1 -165.56(11) . . . . ?
C12 N1 C7 C8 72.73(13) . . . . ?
C12 C11 C16 F1 179.27(13) . . . . ?
C12 C11 C16 C15 -1.8(2) . . . . ?
C12 C13 C14 C15 -0.5(2) . . . . ?
C13 C14 C15 F2 -178.87(15) . . . . ?
C13 C14 C15 C16 1.8(3) . . . . ?
C14 C15 C16 F1 178.31(14) . . . . ?
C14 C15 C16 C11 -0.6(3) . . . . ?
C16 C11 C12 N1 -176.01(13) . . . . ?
C16 C11 C12 C13 3.1(2) . . . . ?
F3 C19 C20 C21 178.19(14) . . . . ?
F4 C18 C19 F3 0.3(2) . . . . ?
F4 C18 C19 C20 -179.77(14) . . . . ?
O4 N2 C22 C17 -28.88(15) . . . . ?
O4 N2 C22 C21 148.62(12) . . . . ?
O4 N2 C26 C25 33.38(12) . . . . ?
O4 N2 C26 C27 -89.16(12) . . . . ?
O4 C24 C25 C26 -19.67(14) . . . . ?
N2 O4 C24 C23 -78.64(13) . . . . ?
N2 O4 C24 C25 42.08(13) . . . . ?
N2 C26 C27 C28 52.09(18) . . . . ?
N2 C26 C27 C32 -131.83(13) . . . . ?
C17 C18 C19 F3 179.60(14) . . . . ?
C17 C18 C19 C20 -0.4(2) . . . . ?
C17 C23 C24 O4 41.98(15) . . . . ?
C17 C23 C24 C25 -71.89(15) . . . . ?
C18 C17 C22 N2 174.30(13) . . . . ?
C18 C17 C22 C21 -3.1(2) . . . . ?
C18 C17 C23 C24 179.13(13) . . . . ?
C18 C19 C20 C21 -1.8(2) . . . . ?
C19 C20 C21 C22 1.5(2) . . . . ?
C20 C21 C22 N2 -176.42(13) . . . . ?
C20 C21 C22 C17 1.0(2) . . . . ?
C22 N2 C26 C25 -80.44(13) . . . . ?
C22 N2 C26 C27 157.02(12) . . . . ?
C22 C17 C18 F4 -177.84(12) . . . . ?
C22 C17 C18 C19 2.8(2) . . . . ?
C22 C17 C23 C24 -2.17(19) . . . . ?
C23 C17 C18 F4 0.9(2) . . . . ?
C23 C17 C18 C19 -178.40(14) . . . . ?
C23 C17 C22 N2 -4.5(2) . . . . ?
C23 C17 C22 C21 178.12(13) . . . . ?
C23 C24 C25 C26 97.01(14) . . . . ?
C24 O4 N2 C22 69.38(12) . . . . ?
C24 O4 N2 C26 -47.78(12) . . . . ?
C24 C25 C26 N2 -8.31(14) . . . . ?
C24 C25 C26 C27 112.99(13) . . . . ?
C25 C26 C27 C28 -65.12(17) . . . . ?
C25 C26 C27 C32 110.95(15) . . . . ?
C26 N2 C22 C17 81.99(15) . . . . ?
C26 N2 C22 C21 -100.51(14) . . . . ?
C26 C27 C28 C29 175.81(14) . . . . ?
C26 C27 C32 C31 -175.76(13) . . . . ?
C27 C28 C29 C30 -0.4(2) . . . . ?
C28 C27 C32 C31 0.5(2) . . . . ?
C28 C29 C30 C31 0.9(2) . . . . ?
C29 C30 C31 C32 -0.8(2) . . . . ?
C30 C31 C32 C27 0.1(2) . . . . ?
C32 C27 C28 C29 -0.3(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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 5.132
_oxdiff_exptl_absorpt_empirical_full_min 0.392
