# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_jll-37-1_0527-2_auto
_database_code_depnum_ccdc_archive 'CCDC 2358542'
loop_
_audit_author_name
_audit_author_address
'chenmaizhuo '
;Northwest Normal University
China
;
_audit_update_record             
;
2025-10-14 deposited with the CCDC.	2026-04-30 downloaded from the CCDC.
;
_audit_creation_date             2024-05-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H16 F2 N2 O2'
_chemical_formula_sum            'C19 H16 F2 N2 O2'
_chemical_formula_weight         342.34
_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                   9.0908(3)
_cell_length_b                   9.5390(4)
_cell_length_c                   9.9620(3)
_cell_angle_alpha                91.586(3)
_cell_angle_beta                 100.371(3)
_cell_angle_gamma                96.622(3)
_cell_volume                     843.06(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4907
_cell_measurement_temperature    301.54(10)
_cell_measurement_theta_max      76.2070
_cell_measurement_theta_min      6.0640
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.870
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79403
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9347
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.077
_diffrn_reflns_theta_min         4.518
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      301.54(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -54.00 -26.00   0.50    0.05    -- -100.00  45.00 120.00   56
  2  ω    -53.00 -27.00   0.50    0.05    -- -100.00  45.00  30.00   52
  3  ω    -53.00 -27.00   0.50    0.05    -- -100.00  45.00   0.00   52
  4  ω    -54.00 -25.00   0.50    0.05    -- -100.00  45.00 -60.00   58
  5  ω    -54.00 -28.00   0.50    0.05    -- -100.00  45.00-150.00   52
  6  ω    -98.00 -32.00   0.50    0.05    -- -100.00   0.00-120.00  132
  7  ω   -176.00-126.00   0.50    0.05    -- -100.00   0.00-120.00  100
  8  ω    -54.00 -29.00   0.50    0.05    -- -100.00  45.00  90.00   50
  9  ω    -54.00 -26.00   0.50    0.05    -- -100.00  45.00 150.00   56
 10  ω    -33.00   1.00   0.50    0.05    --   45.30 -19.00 -60.00   68
 11  ω    -33.00  24.00   0.50    0.05    --   45.30 -19.00  60.00  114
 12  ω    -19.00  39.00   0.50    0.05    --   45.30 -37.00 -60.00  116
 13  ω    -30.00  39.00   0.50    0.05    --   45.30 -37.00-180.00  138
 14  ω     93.00 169.00   0.50    0.05    --  111.87  45.00-120.00  152
 15  ω     68.00 108.00   0.50    0.05    --   45.30 146.00 -43.00   80
 16  ω     91.00 116.00   0.50    0.05    --  111.87 146.00 -43.00   50
 17  ω     79.00 121.00   0.50    0.05    --  111.87 125.00 150.00   84
 18  ω     50.00  98.00   0.50    0.05    --  111.87 -77.00  60.00   96
 19  ω     42.00  67.00   0.50    0.05    --  111.87 -61.00  90.00   50
 20  ω     45.00 103.00   0.50    0.05    --  111.87 -77.00 -60.00  116
 21  ω     39.00  68.00   0.50    0.05    --  111.87 -61.00 -60.00   58
 22  ω     50.00  77.00   0.50    0.05    --  111.87 -77.00-120.00   54
 23  ω     50.00  84.00   0.50    0.05    --  111.87 -94.00-120.00   68
 24  ω     41.00  69.00   0.50    0.05    --  111.87-146.00 -94.00   56
 25  ω     72.00 101.00   0.50    0.05    --  111.87-146.00 -94.00   58
 26  ω     41.00  86.00   0.50    0.05    --  111.87-125.00 -30.00   90
 27  ω     41.00  79.00   0.50    0.05    --  111.87-125.00  71.00   76
 28  ω     84.00 110.00   0.50    0.05    --  111.87-125.00  71.00   52
 29  ω     43.00  97.00   0.50    0.05    --  111.87 -94.00  60.00  108
 30  ω     32.00  57.00   0.50    0.05    --   45.30-125.00  71.00   50
 31  ω     87.00 112.00   0.50    0.05    --  111.87-125.00 -90.00   50
 32  ω     44.00  69.00   0.50    0.05    --   45.30-146.00 -94.00   50
 33  ω   -169.00-100.00   0.50    0.05    -- -100.00 -61.00 150.00  138
 34  ω   -153.00 -82.00   0.50    0.05    -- -100.00-125.00  71.00  142
 35  ω   -111.00 -82.00   0.50    0.05    --  -45.30-146.00 -94.00   58
 36  ω   -137.00 -90.00   0.50    0.05    -- -100.00-146.00 -94.00   94
 37  ω   -169.00-138.00   0.50    0.05    -- -100.00-125.00  30.00   62
 38  ω   -174.00-140.00   0.50    0.05    -- -100.00 -94.00  30.00   68
 39  ω   -129.00 -88.00   0.50    0.05    -- -100.00 -94.00  30.00   82
 40  ω   -131.00-105.00   0.50    0.05    -- -100.00-125.00  30.00   52
 41  ω    -90.00 -19.00   0.50    0.05    --  -45.30 -77.00  90.00  142
 42  ω    -96.00 -70.00   0.50    0.05    --  -45.30 146.00 -43.00   52
 43  ω   -112.00 -71.00   0.50    0.05    -- -100.00 125.00 -90.00   82
 44  ω   -126.00 -91.00   0.50    0.05    -- -100.00 146.00 -43.00   70
 45  ω   -110.00 -85.00   0.50    0.05    -- -100.00 125.00  30.00   50
 46  ω   -111.00 -77.00   0.50    0.05    -- -100.00 125.00 150.00   68
 47  ω    -87.00 -48.00   0.50    0.05    --  -45.30 125.00 150.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0885797000
_diffrn_orient_matrix_UB_12      -0.1436744000
_diffrn_orient_matrix_UB_13      -0.0551828000
_diffrn_orient_matrix_UB_21      -0.0050791000
_diffrn_orient_matrix_UB_22      -0.0425941000
_diffrn_orient_matrix_UB_23      0.1472926000
_diffrn_orient_matrix_UB_31      -0.1491937000
_diffrn_orient_matrix_UB_32      0.0635817000
_diffrn_orient_matrix_UB_33      -0.0060433000
_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                2592
_reflns_number_total             3298
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0751
_refine_ls_restrained_S_all      1.069
_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)+(0.1151P)²+0.2840P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2156
_refine_ls_wR_factor_ref         0.2265
_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 Ternary CH refined with riding coordinates:
 C19(H19)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_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
F1 F 0.7283(3) 0.7112(2) 0.33761(18) 0.0997(6) Uani 1 1 d . . . . .
F2 F 0.8818(2) 0.8348(2) 0.4989(2) 0.0971(6) Uani 1 1 d . . . . .
O1 O 0.8203(2) 0.6282(3) 0.9185(2) 0.0967(8) Uani 1 1 d . . . . .
O2 O 0.6152(3) 0.6492(4) 0.9965(3) 0.1390(14) Uani 1 1 d . . . . .
N1 N 0.6782(2) 0.4649(2) 0.6966(2) 0.0599(5) Uani 1 1 d . . . . .
N2 N 0.7604(2) 0.5253(2) 0.6088(2) 0.0648(6) Uani 1 1 d . . . . .
C1 C 0.5897(3) 0.5465(3) 0.7719(2) 0.0576(6) Uani 1 1 d . . . . .
C2 C 0.2421(5) 0.9098(5) 0.7268(4) 0.1066(13) Uani 1 1 d . . . . .
H2 H 0.232315 1.005185 0.717323 0.128 Uiso 1 1 calc R U . . .
C3 C 0.8089(4) 0.1137(4) 0.6889(4) 0.0866(9) Uani 1 1 d . . . . .
H3 H 0.861098 0.062260 0.636766 0.104 Uiso 1 1 calc R U . . .
C4 C 0.7053(3) 0.3272(3) 0.7331(2) 0.0580(6) Uani 1 1 d . . . . .
C5 C 0.2726(3) 0.6306(4) 0.7579(3) 0.0760(8) Uani 1 1 d . . . . .
H5 H 0.282863 0.535846 0.771235 0.091 Uiso 1 1 calc R U . . .
C6 C 0.5240(3) 0.6601(3) 0.6850(2) 0.0604(6) Uani 1 1 d . . . . .
C7 C 0.7594(4) 0.0539(3) 0.7990(4) 0.0859(9) Uani 1 1 d . . . . .
H7 H 0.777672 -0.037308 0.821230 0.103 Uiso 1 1 calc R U . . .
C8 C 0.6766(3) 0.6145(3) 0.9076(3) 0.0661(7) Uani 1 1 d . . . . .
C9 C 0.9086(4) 0.6985(6) 1.0444(4) 0.1153(15) Uani 1 1 d . . . . .
H9A H 1.009042 0.729016 1.030823 0.173 Uiso 1 1 calc R U . . .
H9B H 0.912417 0.633721 1.116621 0.173 Uiso 1 1 calc R U . . .
H9C H 0.862446 0.778860 1.068357 0.173 Uiso 1 1 calc R U . . .
C10 C 0.3881(3) 0.7165(3) 0.7168(3) 0.0643(6) Uani 1 1 d . . . . .
C11 C 0.6825(4) 0.1303(3) 0.8760(4) 0.0802(8) Uani 1 1 d . . . . .
H11 H 0.647619 0.090037 0.950045 0.096 Uiso 1 1 calc R U . . .
C12 C 0.5975(3) 0.7086(3) 0.5888(3) 0.0684(7) Uani 1 1 d . . . . .
H12 H 0.566676 0.784572 0.539140 0.082 Uiso 1 1 calc R U . . .
C13 C 0.3722(4) 0.8583(4) 0.7027(3) 0.0834(9) Uani 1 1 d . . . . .
H13 H 0.448705 0.919122 0.677015 0.100 Uiso 1 1 calc R U . . .
C14 C 0.7829(3) 0.2479(3) 0.6545(3) 0.0713(7) Uani 1 1 d . . . . .
H14 H 0.816518 0.286456 0.579143 0.086 Uiso 1 1 calc R U . . .
C15 C 0.1426(4) 0.6822(5) 0.7795(4) 0.0927(10) Uani 1 1 d . . . . .
H15 H 0.065125 0.621849 0.804285 0.111 Uiso 1 1 calc R U . . .
C16 C 0.7246(3) 0.6438(3) 0.5615(3) 0.0680(7) Uani 1 1 d . . . . .
C17 C 0.1279(5) 0.8221(5) 0.7643(4) 0.1064(13) Uani 1 1 d . . . . .
H17 H 0.040904 0.857541 0.779427 0.128 Uiso 1 1 calc R U . . .
C18 C 0.6565(3) 0.2669(3) 0.8443(3) 0.0682(7) Uani 1 1 d . . . . .
H18 H 0.605922 0.318167 0.898092 0.082 Uiso 1 1 calc R U . . .
C19 C 0.8180(4) 0.7009(3) 0.4616(3) 0.0806(8) Uani 1 1 d . . . . .
H19 H 0.895747 0.639909 0.452795 0.097 Uiso 1 1 calc R U . . .
H1 H 0.511(3) 0.477(3) 0.794(3) 0.059(7) 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
F1 C19 1.365(4) . ?
F2 C19 1.353(4) . ?
O1 C8 1.282(3) . ?
O1 C9 1.460(4) . ?
O2 C8 1.187(3) . ?
N1 N2 1.349(3) . ?
N1 C1 1.465(3) . ?
N1 C4 1.410(3) . ?
N2 C16 1.291(4) . ?
C1 C6 1.515(4) . ?
C1 C8 1.524(4) . ?
C1 H1 0.98(3) . ?
C2 H2 0.9300 . ?
C2 C13 1.388(5) . ?
C2 C17 1.368(6) . ?
C3 H3 0.9300 . ?
C3 C7 1.372(5) . ?
C3 C14 1.370(5) . ?
C4 C14 1.403(3) . ?
C4 C18 1.381(4) . ?
C5 H5 0.9300 . ?
C5 C10 1.384(4) . ?
C5 C15 1.381(4) . ?
C6 C10 1.484(3) . ?
C6 C12 1.328(4) . ?
C7 H7 0.9300 . ?
C7 C11 1.374(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C13 1.386(4) . ?
C11 H11 0.9300 . ?
C11 C18 1.385(4) . ?
C12 H12 0.9300 . ?
C12 C16 1.434(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C15 C17 1.366(6) . ?
C16 C19 1.495(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19 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 C9 116.7(2) . . ?
N2 N1 C1 121.9(2) . . ?
N2 N1 C4 116.25(19) . . ?
C4 N1 C1 120.7(2) . . ?
C16 N2 N1 117.0(2) . . ?
N1 C1 C6 110.5(2) . . ?
N1 C1 C8 114.31(19) . . ?
N1 C1 H1 104.8(15) . . ?
C6 C1 C8 109.0(2) . . ?
C6 C1 H1 111.8(15) . . ?
C8 C1 H1 106.4(16) . . ?
C13 C2 H2 119.6 . . ?
C17 C2 H2 119.6 . . ?
C17 C2 C13 120.9(4) . . ?
C7 C3 H3 119.4 . . ?
C14 C3 H3 119.4 . . ?
C14 C3 C7 121.2(3) . . ?
C14 C4 N1 119.6(2) . . ?
C18 C4 N1 121.7(2) . . ?
C18 C4 C14 118.6(2) . . ?
C10 C5 H5 119.2 . . ?
C15 C5 H5 119.2 . . ?
C15 C5 C10 121.6(3) . . ?
C10 C6 C1 118.8(2) . . ?
C12 C6 C1 117.3(2) . . ?
C12 C6 C10 123.8(2) . . ?
C3 C7 H7 120.4 . . ?
C3 C7 C11 119.3(3) . . ?
C11 C7 H7 120.4 . . ?
O1 C8 C1 114.6(2) . . ?
O2 C8 O1 123.2(3) . . ?
O2 C8 C1 122.1(3) . . ?
O1 C9 H9A 109.5 . . ?
O1 C9 H9B 109.5 . . ?
O1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C10 C6 122.0(3) . . ?
C5 C10 C13 117.9(3) . . ?
C13 C10 C6 120.1(3) . . ?
C7 C11 H11 119.7 . . ?
C7 C11 C18 120.6(3) . . ?
C18 C11 H11 119.7 . . ?
C6 C12 H12 120.0 . . ?
C6 C12 C16 120.0(3) . . ?
C16 C12 H12 120.0 . . ?
C2 C13 H13 120.0 . . ?
C10 C13 C2 120.1(4) . . ?
C10 C13 H13 120.0 . . ?
C3 C14 C4 120.0(3) . . ?
C3 C14 H14 120.0 . . ?
C4 C14 H14 120.0 . . ?
C5 C15 H15 120.1 . . ?
C17 C15 C5 119.8(4) . . ?
C17 C15 H15 120.1 . . ?
N2 C16 C12 124.1(3) . . ?
N2 C16 C19 113.5(2) . . ?
C12 C16 C19 122.1(3) . . ?
C2 C17 H17 120.2 . . ?
C15 C17 C2 119.7(3) . . ?
C15 C17 H17 120.2 . . ?
C4 C18 C11 120.3(3) . . ?
C4 C18 H18 119.8 . . ?
C11 C18 H18 119.8 . . ?
F1 C19 C16 109.9(3) . . ?
F1 C19 H19 110.3 . . ?
F2 C19 F1 104.7(3) . . ?
F2 C19 C16 111.2(2) . . ?
F2 C19 H19 110.3 . . ?
C16 C19 H19 110.3 . . ?

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 N2 C16 C12 -4.6(4) . . . . ?
N1 N2 C16 C19 -178.1(2) . . . . ?
N1 C1 C6 C10 156.8(2) . . . . ?
N1 C1 C6 C12 -26.8(3) . . . . ?
N1 C1 C8 O1 20.1(4) . . . . ?
N1 C1 C8 O2 -158.6(3) . . . . ?
N1 C4 C14 C3 -179.6(3) . . . . ?
N1 C4 C18 C11 178.8(2) . . . . ?
N2 N1 C1 C6 35.5(3) . . . . ?
N2 N1 C1 C8 -87.9(3) . . . . ?
N2 N1 C4 C14 -16.0(3) . . . . ?
N2 N1 C4 C18 164.5(2) . . . . ?
N2 C16 C19 F1 118.6(3) . . . . ?
N2 C16 C19 F2 -125.9(3) . . . . ?
C1 N1 N2 C16 -20.6(3) . . . . ?
C1 N1 C4 C14 176.3(2) . . . . ?
C1 N1 C4 C18 -3.2(3) . . . . ?
C1 C6 C10 C5 -38.2(3) . . . . ?
C1 C6 C10 C13 143.4(3) . . . . ?
C1 C6 C12 C16 6.2(4) . . . . ?
C3 C7 C11 C18 -0.8(5) . . . . ?
C4 N1 N2 C16 171.8(2) . . . . ?
C4 N1 C1 C6 -157.5(2) . . . . ?
C4 N1 C1 C8 79.1(3) . . . . ?
C5 C10 C13 C2 -1.3(5) . . . . ?
C5 C15 C17 C2 0.5(6) . . . . ?
C6 C1 C8 O1 -104.1(3) . . . . ?
C6 C1 C8 O2 77.2(4) . . . . ?
C6 C10 C13 C2 177.2(3) . . . . ?
C6 C12 C16 N2 11.6(4) . . . . ?
C6 C12 C16 C19 -175.4(3) . . . . ?
C7 C3 C14 C4 0.5(5) . . . . ?
C7 C11 C18 C4 1.2(4) . . . . ?
C8 C1 C6 C10 -76.8(3) . . . . ?
C8 C1 C6 C12 99.6(3) . . . . ?
C9 O1 C8 O2 -3.9(5) . . . . ?
C9 O1 C8 C1 177.4(3) . . . . ?
C10 C5 C15 C17 -2.0(5) . . . . ?
C10 C6 C12 C16 -177.5(2) . . . . ?
C12 C6 C10 C5 145.7(3) . . . . ?
C12 C6 C10 C13 -32.8(4) . . . . ?
C12 C16 C19 F1 -55.0(4) . . . . ?
C12 C16 C19 F2 60.5(4) . . . . ?
C13 C2 C17 C15 0.6(6) . . . . ?
C14 C3 C7 C11 -0.1(5) . . . . ?
C14 C4 C18 C11 -0.7(4) . . . . ?
C15 C5 C10 C6 -176.1(3) . . . . ?
C15 C5 C10 C13 2.4(4) . . . . ?
C17 C2 C13 C10 -0.2(6) . . . . ?
C18 C4 C14 C3 -0.1(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 2.993
_oxdiff_exptl_absorpt_empirical_full_min 0.403
####################################################################### 
# 
# 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_jll-37-2_0527_auto
_database_code_depnum_ccdc_archive 'CCDC 2358543'
loop_
_audit_author_name
_audit_author_address
chen
;qq
China
;
_audit_update_record             
;
2024-05-27 deposited with the CCDC.	2026-04-30 downloaded from the CCDC.
;
_audit_creation_date             2024-05-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H14 F2 N2 O2'
_chemical_formula_sum            'C18 H14 F2 N2 O2'
_chemical_formula_weight         328.31
_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/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                   6.0296(2)
_cell_length_b                   9.1187(4)
_cell_length_c                   28.9024(15)
_cell_angle_alpha                90
_cell_angle_beta                 92.846(4)
_cell_angle_gamma                90
_cell_volume                     1587.16(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3662
_cell_measurement_temperature    301.62(10)
_cell_measurement_theta_max      75.2250
_cell_measurement_theta_min      3.0530
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.902
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49595
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_unetI/netI     0.0638
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            10300
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.376
_diffrn_reflns_theta_min         3.062
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      301.62(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 0.933
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    140.00 171.00   0.50    0.60    --  111.87  61.00-180.00   62
  2  ω    137.00 163.00   0.50    0.60    --  111.87  61.00  90.00   52
  3  ω    134.00 168.00   0.50    0.60    --  111.87  45.00 120.00   68
  4  ω     96.00 130.00   0.50    0.60    --  111.87  61.00  90.00   68
  5  ω    102.00 129.00   0.50    0.60    --  111.87  45.00 120.00   54
  6  ω     40.00  66.00   0.50    0.60    --  111.87 -61.00   0.00   52
  7  ω     53.00  99.00   0.50    0.60    --  111.87 -77.00 -30.00   92
  8  ω     49.00 100.00   0.50    0.60    --  111.87 -77.00 -90.00  102
  9  ω    -29.00  -4.00   0.50    0.54    --   44.30 -19.00 -90.00   50
 10  ω    -33.00  22.00   0.50    0.54    --   44.30 -19.00-180.00  110
 11  ω     69.00  94.00   0.50    0.54    --   44.30 136.00   3.00   50
 12  ω     99.00 124.00   0.50    0.60    --  111.87 133.00-174.00   50
 13  ω    -34.00   8.00   0.50    0.54    --   44.30 -19.00 120.00   84
 14  ω      0.00  35.00   0.50    0.54    --  -44.30  19.00 -30.00   70
 15  ω    -51.00 -25.00   0.50    0.60    -- -100.00  45.00 -60.00   52
 16  ω    -51.00 -25.00   0.50    0.60    -- -100.00  45.00-120.00   52
 17  ω     55.00  80.00   0.50    0.60    --  111.87-136.00 -60.00   50
 18  ω     22.00  62.00   0.50    0.54    --   44.30-133.00 117.00   80
 19  ω    -54.00 -25.00   0.50    0.60    -- -100.00  45.00-180.00   58
 20  ω    -54.00 -25.00   0.50    0.60    -- -100.00  45.00-150.00   58
 21  ω   -111.00 -80.00   0.50    0.60    -- -100.00 125.00  90.00   62
 22  ω   -126.00-101.00   0.50    0.60    -- -100.00 145.00 176.59   50
 23  ω   -124.00 -99.00   0.50    0.60    -- -100.00 142.00  71.07   50
 24  ω    -89.00 -29.00   0.50    0.60    -- -100.00 136.00   3.00  120
 25  ω    -90.00 -65.00   0.50    0.54    --  -44.30 136.00   3.00   50
 26  ω    -99.00 -46.00   0.50    0.54    --  -44.30 133.00-174.00  106
 27  ω   -104.00 -72.00   0.50    0.60    -- -100.00 133.00-174.00   64
 28  ω   -174.00-125.00   0.50    0.60    -- -100.00-136.00 -60.00   98
 29  ω   -141.00 -87.00   0.50    0.60    -- -100.00 -94.00  60.00  108
 30  ω   -125.00 -84.00   0.50    0.60    -- -100.00-133.00 117.00   82
 31  ω   -171.00-145.00   0.50    0.60    -- -100.00 -94.00  60.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0128841000
_diffrn_orient_matrix_UB_12      0.1498547000
_diffrn_orient_matrix_UB_13      -0.0246335000
_diffrn_orient_matrix_UB_21      -0.0290338000
_diffrn_orient_matrix_UB_22      -0.0780879000
_diffrn_orient_matrix_UB_23      -0.0471854000
_diffrn_orient_matrix_UB_31      -0.2537357000
_diffrn_orient_matrix_UB_32      0.0014856000
_diffrn_orient_matrix_UB_33      0.0039761000
_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                2157
_reflns_number_total             3156
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.589
_refine_diff_density_min         -0.629
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3156
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.1166
_refine_ls_R_factor_gt           0.0901
_refine_ls_restrained_S_all      1.153
_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)+(0.1491P)²+0.9732P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2567
_refine_ls_wR_factor_ref         0.2871
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F3) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F4) \\sim Ueq, Uanis(F1) \\sim
Ueq: with sigma of 0.004 and sigma for terminal atoms of 0.002
3. Others
 Fixed Sof: F1(0.75) F2(0.25) F3(0.75) F4(0.25) H3A(0.75) H3B(0.25)
4.a Ternary CH refined with riding coordinates:
 C3(H3A), C3(H3B)
4.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C13(H13), C14(H14),
 C17(H17), C18(H18)
4.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C)
;
_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 0.3982(8) 0.1134(5) 0.39960(16) 0.1088(13) Uani 0.75 1 d . U P A 1
F2 F 0.514(2) 0.1409(15) 0.4418(5) 0.099(3) Uani 0.25 1 d . U P A 2
F3 F 0.4333(8) 0.1853(5) 0.46816(17) 0.1081(13) Uani 0.75 1 d . U P A 1
F4 F 0.1658(18) 0.2219(13) 0.4476(4) 0.087(3) Uani 0.25 1 d . U P A 2
O1 O 0.0799(4) 0.4819(4) 0.30462(10) 0.0764(8) Uani 1 1 d . . . . .
O2 O 0.0327(5) 0.2875(4) 0.34983(13) 0.0914(11) Uani 1 1 d . . . . .
N1 N 0.5991(4) 0.5580(3) 0.40759(10) 0.0530(7) Uani 1 1 d . . . . .
N2 N 0.5739(5) 0.4305(3) 0.43124(11) 0.0612(8) Uani 1 1 d . . . . .
C1 C 0.7664(5) 0.6582(4) 0.42479(12) 0.0522(8) Uani 1 1 d . . . . .
C2 C -0.1551(7) 0.2439(6) 0.3209(2) 0.0942(16) Uani 1 1 d . . . . .
H2A H -0.108499 0.223330 0.290325 0.141 Uiso 1 1 calc R U . . .
H2B H -0.262589 0.321675 0.319526 0.141 Uiso 1 1 calc R U . . .
H2C H -0.220260 0.157600 0.333548 0.141 Uiso 1 1 calc R U . . .
C3 C 0.3369(7) 0.2172(5) 0.42602(17) 0.0733(11) Uani 1 1 d . . . . .
H3A H 0.175023 0.215174 0.427754 0.088 Uiso 0.75 1 calc R U P A 1
H3B H 0.289900 0.165370 0.397498 0.088 Uiso 0.25 1 calc R U P A 2
C4 C 0.2823(9) 0.9103(5) 0.3048(2) 0.0939(16) Uani 1 1 d . . . . .
H4 H 0.164029 0.975681 0.302177 0.113 Uiso 1 1 calc R U . . .
C5 C 1.0969(6) 0.8411(5) 0.46015(13) 0.0685(10) Uani 1 1 d . . . . .
H5 H 1.208958 0.903125 0.471641 0.082 Uiso 1 1 calc R U . . .
C6 C 0.9038(7) 0.8993(5) 0.44017(14) 0.0696(10) Uani 1 1 d . . . . .
H6 H 0.885966 1.000466 0.438301 0.084 Uiso 1 1 calc R U . . .
C7 C 0.4686(11) 0.9322(6) 0.27937(19) 0.1017(19) Uani 1 1 d . . . . .
H7 H 0.473973 1.011701 0.259294 0.122 Uiso 1 1 calc R U . . .
C8 C 0.3214(5) 0.4455(4) 0.37085(12) 0.0530(8) Uani 1 1 d . . . . .
C9 C 0.4066(6) 0.3626(4) 0.40906(14) 0.0614(9) Uani 1 1 d . . . . .
C10 C 0.2732(6) 0.7901(5) 0.33431(16) 0.0689(10) Uani 1 1 d . . . . .
H10 H 0.147804 0.773560 0.351063 0.083 Uiso 1 1 calc R U . . .
C11 C 0.9602(5) 0.5996(4) 0.44529(12) 0.0578(9) Uani 1 1 d . . . . .
H11 H 0.979305 0.498463 0.446976 0.069 Uiso 1 1 calc R U . . .
C12 C 0.4521(5) 0.6955(4) 0.33847(12) 0.0517(8) Uani 1 1 d . . . . .
C13 C 0.7365(6) 0.8074(4) 0.42289(13) 0.0583(9) Uani 1 1 d . . . . .
H13 H 0.604822 0.846434 0.410091 0.070 Uiso 1 1 calc R U . . .
C14 C 0.6443(9) 0.8377(6) 0.28363(16) 0.0855(14) Uani 1 1 d . . . . .
H14 H 0.769236 0.853451 0.266695 0.103 Uiso 1 1 calc R U . . .
C15 C 0.1357(5) 0.4109(4) 0.33805(14) 0.0572(9) Uani 1 1 d . . . . .
C16 C 0.4513(5) 0.5709(4) 0.37064(11) 0.0496(8) Uani 1 1 d . . . . .
C17 C 1.1240(6) 0.6921(5) 0.46310(14) 0.0649(10) Uani 1 1 d . . . . .
H17 H 1.253149 0.653278 0.477149 0.078 Uiso 1 1 calc R U . . .
C18 C 0.6365(6) 0.7212(5) 0.31243(13) 0.0640(10) Uani 1 1 d . . . . .
H18 H 0.756505 0.657135 0.314921 0.077 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 C3 1.282(6) . ?
F2 C3 1.336(13) . ?
F3 C3 1.355(6) . ?
F4 C3 1.233(11) . ?
O1 C15 1.197(5) . ?
O2 C2 1.429(5) . ?
O2 C15 1.338(5) . ?
N1 N2 1.362(4) . ?
N1 C1 1.431(4) . ?
N1 C16 1.361(4) . ?
N2 C9 1.322(5) . ?
C1 C11 1.391(5) . ?
C1 C13 1.373(5) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 C9 1.482(6) . ?
C4 H4 0.9300 . ?
C4 C7 1.387(9) . ?
C4 C10 1.391(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(6) . ?
C5 C17 1.371(6) . ?
C6 H6 0.9300 . ?
C6 C13 1.386(5) . ?
C7 H7 0.9300 . ?
C7 C14 1.366(8) . ?
C8 C9 1.413(5) . ?
C8 C15 1.465(5) . ?
C8 C16 1.387(5) . ?
C10 H10 0.9300 . ?
C10 C12 1.382(5) . ?
C11 H11 0.9300 . ?
C11 C17 1.379(5) . ?
C12 C16 1.468(5) . ?
C12 C18 1.393(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C14 C18 1.351(6) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O2 C2 116.7(4) . . ?
N2 N1 C1 117.7(3) . . ?
C16 N1 N2 112.5(3) . . ?
C16 N1 C1 129.8(3) . . ?
C9 N2 N1 104.9(3) . . ?
C11 C1 N1 117.7(3) . . ?
C13 C1 N1 122.0(3) . . ?
C13 C1 C11 120.3(3) . . ?
O2 C2 H2A 109.5 . . ?
O2 C2 H2B 109.5 . . ?
O2 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
F1 C3 F3 104.7(4) . . ?
F1 C3 H3A 109.5 . . ?
F1 C3 C9 111.6(4) . . ?
F2 C3 H3B 103.2 . . ?
F2 C3 C9 110.1(6) . . ?
F3 C3 H3A 109.5 . . ?
F3 C3 C9 111.9(4) . . ?
F4 C3 F2 121.3(9) . . ?
F4 C3 H3B 103.2 . . ?
F4 C3 C9 113.3(6) . . ?
C9 C3 H3A 109.5 . . ?
C9 C3 H3B 103.2 . . ?
C7 C4 H4 120.1 . . ?
C7 C4 C10 119.8(5) . . ?
C10 C4 H4 120.1 . . ?
C6 C5 H5 119.9 . . ?
C17 C5 H5 119.9 . . ?
C17 C5 C6 120.2(4) . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C13 120.1(4) . . ?
C13 C6 H6 119.9 . . ?
C4 C7 H7 119.8 . . ?
C14 C7 C4 120.4(4) . . ?
C14 C7 H7 119.8 . . ?
C9 C8 C15 128.8(3) . . ?
C16 C8 C9 105.1(3) . . ?
C16 C8 C15 126.0(3) . . ?
N2 C9 C3 118.7(3) . . ?
N2 C9 C8 111.6(3) . . ?
C8 C9 C3 129.7(3) . . ?
C4 C10 H10 120.3 . . ?
C12 C10 C4 119.4(4) . . ?
C12 C10 H10 120.3 . . ?
C1 C11 H11 120.2 . . ?
C17 C11 C1 119.7(4) . . ?
C17 C11 H11 120.2 . . ?
C10 C12 C16 120.7(3) . . ?
C10 C12 C18 119.2(3) . . ?
C18 C12 C16 120.0(3) . . ?
C1 C13 C6 119.5(3) . . ?
C1 C13 H13 120.2 . . ?
C6 C13 H13 120.2 . . ?
C7 C14 H14 120.0 . . ?
C18 C14 C7 120.1(5) . . ?
C18 C14 H14 120.0 . . ?
O1 C15 O2 123.0(3) . . ?
O1 C15 C8 125.5(3) . . ?
O2 C15 C8 111.5(3) . . ?
N1 C16 C8 105.9(3) . . ?
N1 C16 C12 122.7(3) . . ?
C8 C16 C12 131.3(3) . . ?
C5 C17 C11 120.1(4) . . ?
C5 C17 H17 119.9 . . ?
C11 C17 H17 119.9 . . ?
C12 C18 H18 119.4 . . ?
C14 C18 C12 121.2(4) . . ?
C14 C18 H18 119.4 . . ?

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 C3 C9 N2 -105.8(5) . . . . ?
F1 C3 C9 C8 73.6(6) . . . . ?
F2 C3 C9 N2 -36.2(9) . . . . ?
F2 C3 C9 C8 143.2(8) . . . . ?
F3 C3 C9 N2 11.2(6) . . . . ?
F3 C3 C9 C8 -169.4(4) . . . . ?
F4 C3 C9 N2 103.3(7) . . . . ?
F4 C3 C9 C8 -77.3(8) . . . . ?
N1 N2 C9 C3 179.4(3) . . . . ?
N1 N2 C9 C8 -0.1(4) . . . . ?
N1 C1 C11 C17 -178.8(3) . . . . ?
N1 C1 C13 C6 179.8(3) . . . . ?
N2 N1 C1 C11 34.4(4) . . . . ?
N2 N1 C1 C13 -143.4(3) . . . . ?
N2 N1 C16 C8 0.9(4) . . . . ?
N2 N1 C16 C12 -177.0(3) . . . . ?
C1 N1 N2 C9 178.0(3) . . . . ?
C1 N1 C16 C8 -177.4(3) . . . . ?
C1 N1 C16 C12 4.7(5) . . . . ?
C1 C11 C17 C5 -0.7(6) . . . . ?
C2 O2 C15 O1 -1.5(6) . . . . ?
C2 O2 C15 C8 178.6(4) . . . . ?
C4 C7 C14 C18 0.6(8) . . . . ?
C4 C10 C12 C16 177.6(4) . . . . ?
C4 C10 C12 C18 -1.0(6) . . . . ?
C5 C6 C13 C1 -1.5(6) . . . . ?
C6 C5 C17 C11 1.3(6) . . . . ?
C7 C4 C10 C12 1.2(7) . . . . ?
C7 C14 C18 C12 -0.5(7) . . . . ?
C9 C8 C15 O1 -175.2(4) . . . . ?
C9 C8 C15 O2 4.6(5) . . . . ?
C9 C8 C16 N1 -0.8(4) . . . . ?
C9 C8 C16 C12 176.8(3) . . . . ?
C10 C4 C7 C14 -1.0(8) . . . . ?
C10 C12 C16 N1 -116.6(4) . . . . ?
C10 C12 C16 C8 66.1(5) . . . . ?
C10 C12 C18 C14 0.7(6) . . . . ?
C11 C1 C13 C6 2.1(5) . . . . ?
C13 C1 C11 C17 -1.0(5) . . . . ?
C15 C8 C9 N2 -179.0(3) . . . . ?
C15 C8 C9 C3 1.6(7) . . . . ?
C15 C8 C16 N1 178.7(3) . . . . ?
C15 C8 C16 C12 -3.6(6) . . . . ?
C16 N1 N2 C9 -0.5(4) . . . . ?
C16 N1 C1 C11 -147.4(3) . . . . ?
C16 N1 C1 C13 34.8(5) . . . . ?
C16 C8 C9 N2 0.6(4) . . . . ?
C16 C8 C9 C3 -178.8(4) . . . . ?
C16 C8 C15 O1 5.3(6) . . . . ?
C16 C8 C15 O2 -174.9(3) . . . . ?
C16 C12 C18 C14 -178.0(4) . . . . ?
C17 C5 C6 C13 -0.1(6) . . . . ?
C18 C12 C16 N1 62.1(5) . . . . ?
C18 C12 C16 C8 -115.2(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 3.868
_oxdiff_exptl_absorpt_empirical_full_min 0.359
