# 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. 
# 
#######################################################################

data_7
_database_code_depnum_ccdc_archive 'CCDC 2352134'
loop_
_audit_author_name
_audit_author_address
'Xuesen Fan'
;Henan Normal University
China
;
_audit_update_record             
;
2024-04-30 deposited with the CCDC.	2024-05-29 downloaded from the CCDC.
;
_audit_creation_date             2024-03-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H11 F3 N2 O4'
_chemical_formula_sum            'C17 H11 F3 N2 O4'
_chemical_formula_weight         364.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
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                   9.7758(4)
_cell_length_b                   10.5130(5)
_cell_length_c                   11.2193(5)
_cell_angle_alpha                90.001(4)
_cell_angle_beta                 112.552(4)
_cell_angle_gamma                105.120(4)
_cell_volume                     1021.51(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2769
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8630
_cell_measurement_theta_min      4.2870
_shelx_estimated_absorpt_T_max   0.915
_shelx_estimated_absorpt_T_min   0.841
_exptl_absorpt_coefficient_mu    0.899
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92055
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.109a (Rigaku Oxford Diffraction, 2024)
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    1.184
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7312
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.621
_diffrn_reflns_theta_min         4.294
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -103.00 -78.00   1.00    1.89    --  -35.62-160.00  76.00   25
  2  ω    -65.00 -39.00   1.00    1.89    --  -35.62 118.00 -44.00   26
  3  ω     41.00  82.00   1.00    1.89    --   35.62-118.00-131.00   41
  4  ω     76.00 106.00   1.00    1.89    --   35.62-160.00  76.00   30
  5  ω     83.00 110.00   1.00    7.57    --  106.81 160.00 107.00   27
  6  ω     42.00 108.00   1.00    7.57    --  106.81-118.00-131.00   66
  7  ω     67.00  92.00   1.00    7.57    --  106.81-160.00  76.00   25
  8  ω    119.00 144.00   1.00    7.57    --  106.81 160.00 107.00   25
  9  ω    113.00 138.00   1.00    7.57    --  106.81 118.00 -44.00   25
 10  ω   -104.00 -17.00   1.00    1.89    --  -35.62 -38.00  60.00   87
 11  ω    -91.00 -66.00   1.00    1.89    --  -35.62 160.00 107.00   25
 12  ω     17.00  74.00   1.00    1.89    --   35.62 -99.00  90.00   57
 13  ω    -24.00  48.00   1.00    1.89    --   35.62 -38.00 -60.00   72
 14  ω    -14.00  23.00   1.00    1.89    --   35.62 -77.00  30.00   37
 15  ω     19.00  98.00   1.00    1.89    --   35.62  38.00-150.00   79
 16  ω    -23.00  53.00   1.00    1.89    --   35.62 -38.00-150.00   76
 17  ω    -18.00  33.00   1.00    1.89    --   35.62 -77.00 -60.00   51
 18  ω     91.00 174.00   1.00    7.57    --  106.81  45.00 -30.00   83
 19  ω    104.00 135.00   1.00    7.57    --  106.81 111.00  60.00   31
 20  ω     40.00 124.00   1.00    7.57    --  106.81 -45.00-180.00   84
 21  ω    147.00 172.00   1.00    7.57    --  106.81 111.00  60.00   25
 22  ω     65.00 108.00   1.00    7.57    --  106.81-111.00   0.00   43
 23  ω     58.00 114.00   1.00    7.57    --  106.81 -45.00 -90.00   56
 24  ω     40.00 105.00   1.00    7.57    --  106.81 -95.00  60.00   65
 25  ω     70.00 132.00   1.00    7.57    --  106.81 178.00-120.00   62
 26  ω     90.00 115.00   1.00    7.57    --  106.81 -45.00  90.00   25
 27  ω     53.00  83.00   1.00    7.57    --  106.81 -45.00  90.00   30
 28  ω     65.00 105.00   1.00    7.57    --  106.81-111.00 -90.00   40
 29  ω     41.00  68.00   1.00    7.57    --  106.81-111.00 120.00   27
 30  ω     92.00 175.00   1.00    7.57    --  106.81  30.00-120.00   83
 31  ω    118.00 162.00   1.00    7.57    --  106.81  77.00-180.00   44
 32  ω     52.00 127.00   1.00    7.57    --  106.81 -30.00   0.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0223132000
_diffrn_orient_matrix_UB_12      -0.1391167000
_diffrn_orient_matrix_UB_13      -0.0072718000
_diffrn_orient_matrix_UB_21      0.0932966000
_diffrn_orient_matrix_UB_22      0.0188442000
_diffrn_orient_matrix_UB_23      0.1480347000
_diffrn_orient_matrix_UB_31      -0.1497986000
_diffrn_orient_matrix_UB_32      -0.0602202000
_diffrn_orient_matrix_UB_33      0.0205267000
_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                2915
_reflns_number_total             3851
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.43.109a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.109a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.109a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.715
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.059
_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     237
_refine_ls_number_reflns         3851
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0680
_refine_ls_restrained_S_all      1.059
_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)+(0.1079P)²+0.4647P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2064
_refine_ls_wR_factor_ref         0.2177
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 O3(H3)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3A), C4(H4), C5(H5), C9(H9), C11(H11)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.2928(3) 0.2425(3) -0.0270(2) 0.1035(8) Uani 1 1 d . . . . .
F2 F 0.5216(3) 0.3711(3) 0.0674(3) 0.1013(7) Uani 1 1 d . . . . .
F3 F 0.4741(3) 0.1649(2) 0.0921(2) 0.1010(8) Uani 1 1 d . . . . .
O1 O 0.9204(4) 0.2294(4) 0.5710(3) 0.1071(10) Uani 1 1 d . . . . .
O2 O 0.9855(3) 0.4383(3) 0.6583(2) 0.0859(8) Uani 1 1 d . . . . .
O3 O 0.2852(3) 0.1811(2) 0.2096(3) 0.0776(7) Uani 1 1 d . . . . .
H3 H 0.232432 0.192839 0.255424 0.093 Uiso 1 1 d R U . . .
O4 O 0.0839(2) 0.3643(2) 0.0346(2) 0.0623(5) Uani 1 1 d . . . . .
N1 N 0.5326(3) 0.3341(2) 0.3134(2) 0.0585(6) Uani 1 1 d . . . . .
N2 N 0.1916(3) 0.5760(2) 0.1311(2) 0.0540(6) Uani 1 1 d . . . . .
H2 H 0.109321 0.594964 0.081163 0.065 Uiso 1 1 calc R U . . .
C1 C 0.3062(3) 0.6768(3) 0.2194(3) 0.0517(6) Uani 1 1 d . . . . .
C2 C 0.2871(4) 0.8033(3) 0.2251(3) 0.0647(8) Uani 1 1 d . . . . .
H2A H 0.196619 0.820064 0.168922 0.078 Uiso 1 1 calc R U . . .
C3 C 0.4016(4) 0.9024(3) 0.3133(4) 0.0741(9) Uani 1 1 d . . . . .
H3A H 0.388432 0.986650 0.316452 0.089 Uiso 1 1 calc R U . . .
C4 C 0.5380(4) 0.8797(3) 0.3988(4) 0.0730(9) Uani 1 1 d . . . . .
H4 H 0.614908 0.948463 0.458285 0.088 Uiso 1 1 calc R U . . .
C5 C 0.5587(4) 0.7563(3) 0.3954(3) 0.0610(7) Uani 1 1 d . . . . .
H5 H 0.649786 0.741345 0.452739 0.073 Uiso 1 1 calc R U . . .
C6 C 0.4435(3) 0.6523(3) 0.3059(3) 0.0495(6) Uani 1 1 d . . . . .
C7 C 0.4537(3) 0.5208(3) 0.2925(3) 0.0485(6) Uani 1 1 d . . . . .
C8 C 0.5772(3) 0.4639(3) 0.3675(3) 0.0516(6) Uani 1 1 d . . . . .
C9 C 0.7160(3) 0.4862(3) 0.4713(3) 0.0557(7) Uani 1 1 d . . . . .
H9 H 0.772455 0.564579 0.526133 0.067 Uiso 1 1 calc R U . . .
C10 C 0.7560(3) 0.3653(3) 0.4780(3) 0.0607(7) Uani 1 1 d . . . . .
C11 C 0.6418(4) 0.2739(3) 0.3807(3) 0.0639(8) Uani 1 1 d . . . . .
H11 H 0.639355 0.186574 0.363639 0.077 Uiso 1 1 calc R U . . .
C12 C 0.1960(3) 0.4480(3) 0.1151(3) 0.0518(6) Uani 1 1 d . . . . .
C13 C 0.3400(3) 0.4253(3) 0.1992(3) 0.0510(6) Uani 1 1 d . . . . .
C14 C 0.3842(3) 0.2964(3) 0.1999(3) 0.0589(7) Uani 1 1 d . . . . .
C15 C 0.4183(4) 0.2704(4) 0.0818(4) 0.0732(9) Uani 1 1 d . . . . .
C16 C 0.8937(4) 0.3346(4) 0.5708(3) 0.0727(9) Uani 1 1 d . . . . .
C17 C 1.1217(4) 0.4171(7) 0.7580(4) 0.117(2) Uani 1 1 d . . . . .
H17A H 1.167788 0.368318 0.719438 0.175 Uiso 1 1 calc R U . . .
H17B H 1.093616 0.367647 0.821075 0.175 Uiso 1 1 calc R U . . .
H17C H 1.194380 0.501116 0.799643 0.175 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 C15 1.320(4) . ?
F2 C15 1.316(5) . ?
F3 C15 1.345(4) . ?
O1 C16 1.201(5) . ?
O2 C16 1.331(5) . ?
O2 C17 1.445(4) . ?
O3 H3 0.8840 . ?
O3 C14 1.373(4) . ?
O4 C12 1.236(3) . ?
N1 C8 1.381(4) . ?
N1 C11 1.358(4) . ?
N1 C14 1.471(3) . ?
N2 H2 0.8600 . ?
N2 C1 1.374(3) . ?
N2 C12 1.371(4) . ?
C1 C2 1.395(4) . ?
C1 C6 1.411(4) . ?
C2 H2A 0.9300 . ?
C2 C3 1.364(5) . ?
C3 H3A 0.9300 . ?
C3 C4 1.393(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.367(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.401(4) . ?
C6 C7 1.424(4) . ?
C7 C8 1.457(4) . ?
C7 C13 1.365(4) . ?
C8 C9 1.369(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.418(4) . ?
C10 C11 1.367(5) . ?
C10 C16 1.467(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.444(4) . ?
C13 C14 1.526(4) . ?
C14 C15 1.526(5) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 O2 C17 115.8(4) . . ?
C14 O3 H3 113.6 . . ?
C8 N1 C14 114.2(2) . . ?
C11 N1 C8 109.4(3) . . ?
C11 N1 C14 136.4(3) . . ?
C1 N2 H2 116.9 . . ?
C12 N2 H2 116.9 . . ?
C12 N2 C1 126.3(2) . . ?
N2 C1 C2 120.4(2) . . ?
N2 C1 C6 119.9(2) . . ?
C2 C1 C6 119.6(3) . . ?
C1 C2 H2A 120.1 . . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 H2A 120.1 . . ?
C2 C3 H3A 119.4 . . ?
C2 C3 C4 121.1(3) . . ?
C4 C3 H3A 119.4 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.3(3) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C7 115.8(2) . . ?
C5 C6 C1 119.1(3) . . ?
C5 C6 C7 125.1(3) . . ?
C6 C7 C8 129.1(2) . . ?
C13 C7 C6 122.2(2) . . ?
C13 C7 C8 108.7(2) . . ?
N1 C8 C7 106.2(2) . . ?
C9 C8 N1 108.4(3) . . ?
C9 C8 C7 145.3(3) . . ?
C8 C9 H9 127.0 . . ?
C8 C9 C10 105.9(3) . . ?
C10 C9 H9 127.0 . . ?
C9 C10 C16 128.7(3) . . ?
C11 C10 C9 108.9(2) . . ?
C11 C10 C16 122.5(3) . . ?
N1 C11 C10 107.4(3) . . ?
N1 C11 H11 126.3 . . ?
C10 C11 H11 126.3 . . ?
O4 C12 N2 120.6(2) . . ?
O4 C12 C13 125.9(3) . . ?
N2 C12 C13 113.5(2) . . ?
C7 C13 C12 122.1(2) . . ?
C7 C13 C14 111.7(2) . . ?
C12 C13 C14 126.3(2) . . ?
O3 C14 N1 112.6(3) . . ?
O3 C14 C13 118.7(3) . . ?
O3 C14 C15 106.8(3) . . ?
N1 C14 C13 99.1(2) . . ?
N1 C14 C15 107.3(3) . . ?
C13 C14 C15 111.9(3) . . ?
F1 C15 F3 105.9(3) . . ?
F1 C15 C14 112.1(3) . . ?
F2 C15 F1 108.1(3) . . ?
F2 C15 F3 106.8(3) . . ?
F2 C15 C14 112.7(3) . . ?
F3 C15 C14 110.8(3) . . ?
O1 C16 O2 123.6(3) . . ?
O1 C16 C10 125.2(4) . . ?
O2 C16 C10 111.2(3) . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
O3 C14 C15 F1 62.4(4) . . . . ?
O3 C14 C15 F2 -175.3(3) . . . . ?
O3 C14 C15 F3 -55.7(3) . . . . ?
O4 C12 C13 C7 -174.8(3) . . . . ?
O4 C12 C13 C14 3.4(5) . . . . ?
N1 C8 C9 C10 0.6(3) . . . . ?
N1 C14 C15 F1 -176.6(3) . . . . ?
N1 C14 C15 F2 -54.4(3) . . . . ?
N1 C14 C15 F3 65.2(3) . . . . ?
N2 C1 C2 C3 179.9(3) . . . . ?
N2 C1 C6 C5 -179.8(3) . . . . ?
N2 C1 C6 C7 1.1(4) . . . . ?
N2 C12 C13 C7 5.3(4) . . . . ?
N2 C12 C13 C14 -176.6(3) . . . . ?
C1 N2 C12 O4 177.9(3) . . . . ?
C1 N2 C12 C13 -2.1(4) . . . . ?
C1 C2 C3 C4 -0.2(6) . . . . ?
C1 C6 C7 C8 -178.7(3) . . . . ?
C1 C6 C7 C13 2.0(4) . . . . ?
C2 C1 C6 C5 -0.4(4) . . . . ?
C2 C1 C6 C7 -179.4(3) . . . . ?
C2 C3 C4 C5 -0.1(6) . . . . ?
C3 C4 C5 C6 0.2(6) . . . . ?
C4 C5 C6 C1 0.1(5) . . . . ?
C4 C5 C6 C7 179.0(3) . . . . ?
C5 C6 C7 C8 2.4(5) . . . . ?
C5 C6 C7 C13 -176.9(3) . . . . ?
C6 C1 C2 C3 0.5(5) . . . . ?
C6 C7 C8 N1 -178.4(3) . . . . ?
C6 C7 C8 C9 4.5(7) . . . . ?
C6 C7 C13 C12 -5.5(4) . . . . ?
C6 C7 C13 C14 176.1(3) . . . . ?
C7 C8 C9 C10 177.8(4) . . . . ?
C7 C13 C14 O3 126.0(3) . . . . ?
C7 C13 C14 N1 4.0(3) . . . . ?
C7 C13 C14 C15 -108.9(3) . . . . ?
C8 N1 C11 C10 0.1(4) . . . . ?
C8 N1 C14 O3 -129.7(3) . . . . ?
C8 N1 C14 C13 -3.4(3) . . . . ?
C8 N1 C14 C15 113.1(3) . . . . ?
C8 C7 C13 C12 175.1(3) . . . . ?
C8 C7 C13 C14 -3.3(3) . . . . ?
C8 C9 C10 C11 -0.6(4) . . . . ?
C8 C9 C10 C16 179.8(3) . . . . ?
C9 C10 C11 N1 0.3(4) . . . . ?
C9 C10 C16 O1 179.9(4) . . . . ?
C9 C10 C16 O2 1.4(5) . . . . ?
C11 N1 C8 C7 -178.8(2) . . . . ?
C11 N1 C8 C9 -0.5(4) . . . . ?
C11 N1 C14 O3 51.0(5) . . . . ?
C11 N1 C14 C13 177.3(4) . . . . ?
C11 N1 C14 C15 -66.2(5) . . . . ?
C11 C10 C16 O1 0.3(6) . . . . ?
C11 C10 C16 O2 -178.3(3) . . . . ?
C12 N2 C1 C2 179.6(3) . . . . ?
C12 N2 C1 C6 -1.0(5) . . . . ?
C12 C13 C14 O3 -52.3(4) . . . . ?
C12 C13 C14 N1 -174.3(3) . . . . ?
C12 C13 C14 C15 72.8(4) . . . . ?
C13 C7 C8 N1 1.0(3) . . . . ?
C13 C7 C8 C9 -176.1(4) . . . . ?
C13 C14 C15 F1 -69.0(4) . . . . ?
C13 C14 C15 F2 53.3(4) . . . . ?
C13 C14 C15 F3 172.8(3) . . . . ?
C14 N1 C8 C7 1.7(3) . . . . ?
C14 N1 C8 C9 -180.0(3) . . . . ?
C14 N1 C11 C10 179.4(3) . . . . ?
C16 C10 C11 N1 180.0(3) . . . . ?
C17 O2 C16 O1 -1.1(6) . . . . ?
C17 O2 C16 C10 177.5(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.574 0.000 -0.872 297.7 89.4 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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 1.390
_oxdiff_exptl_absorpt_empirical_full_min 0.724
####################################################################### 
# 
# 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_3ra
_database_code_depnum_ccdc_archive 'CCDC 2352143'
loop_
_audit_author_name
_audit_author_address
'Xuesen Fan'
;Henan Normal University
China
;
_audit_update_record             
;
2024-04-30 deposited with the CCDC.	2024-05-29 downloaded from the CCDC.
;
_audit_creation_date             2023-12-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H15 F3 N2 O3'
_chemical_formula_sum            'C17 H15 F3 N2 O3'
_chemical_formula_weight         352.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
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                   10.9356(7)
_cell_length_b                   17.2071(9)
_cell_length_c                   9.5578(5)
_cell_angle_alpha                90
_cell_angle_beta                 113.916(7)
_cell_angle_gamma                90
_cell_volume                     1644.07(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3881
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.2390
_cell_measurement_theta_min      5.1110
_shelx_estimated_absorpt_T_max   0.903
_shelx_estimated_absorpt_T_min   0.818
_exptl_absorpt_coefficient_mu    1.044
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.879
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6475
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.798
_diffrn_reflns_theta_min         4.423
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.879
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -77.00 -36.00   1.00    1.00    --  -35.62 111.00 133.00   41
  2  ω     34.00  74.00   1.00    1.00    --   35.62-111.00  39.00   40
  3  ω    110.00 168.00   1.00    1.72    --  106.81 111.00 133.00   58
  4  ω     75.00 101.00   1.00    1.72    --  106.81-111.00  39.00   26
  5  ω    -65.00  23.00   1.00    1.00    --  -35.62  19.00-150.00   88
  6  ω     17.00  83.00   1.00    1.00    --   35.62  38.00 -30.00   66
  7  ω    -15.00  52.00   1.00    1.00    --   35.62 -57.00 -60.00   67
  8  ω     68.00 102.00   1.00    1.00    --   35.62 178.00-180.00   34
  9  ω     37.00  95.00   1.00    1.72    --  106.81 -95.00  60.00   58
 10  ω     52.00  96.00   1.00    1.72    --  106.81-111.00-150.00   44
 11  ω    112.00 160.00   1.00    1.72    --  106.81  77.00  30.00   48
 12  ω    106.00 163.00   1.00    1.72    --  106.81  77.00 -60.00   57
 13  ω     54.00 106.00   1.00    1.72    --  106.81-111.00 120.00   52
 14  ω    105.00 175.00   1.00    1.72    --  106.81  45.00-180.00   70
 15  ω     91.00 117.00   1.00    1.72    --  106.81  61.00 -90.00   26
 16  ω    143.00 174.00   1.00    1.72    --  106.81  61.00 -90.00   31
 17  ω     38.00 113.00   1.00    1.72    --  106.81 -30.00   0.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0936870000
_diffrn_orient_matrix_UB_12      -0.0058360000
_diffrn_orient_matrix_UB_13      -0.0841130000
_diffrn_orient_matrix_UB_21      -0.0326958000
_diffrn_orient_matrix_UB_22      -0.0872008000
_diffrn_orient_matrix_UB_23      -0.0284281000
_diffrn_orient_matrix_UB_31      -0.1179257000
_diffrn_orient_matrix_UB_32      0.0194937000
_diffrn_orient_matrix_UB_33      -0.1522820000
_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                2633
_reflns_number_total             3142
_reflns_odcompleteness_completeness 99.41
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0531
_refine_ls_restrained_S_all      1.104
_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)+(0.0631P)²+1.0075P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1416
_refine_ls_wR_factor_ref         0.1518
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3A), C4(H4), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C11(H11A,H11B,H11C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.97175(14) 0.43095(10) 0.56950(18) 0.0535(4) Uani 1 1 d . . . . .
F2 F 0.84743(16) 0.42064(12) 0.33156(17) 0.0609(5) Uani 1 1 d . . . . .
F3 F 0.92068(16) 0.31880(10) 0.4686(3) 0.0683(6) Uani 1 1 d . . . . .
O1 O 0.7224(2) 0.13234(9) 0.4749(2) 0.0488(5) Uani 1 1 d . . . . .
O2 O 0.64391(17) 0.22842(9) 0.23304(16) 0.0365(4) Uani 1 1 d . . . . .
O3 O 0.79361(16) 0.36784(10) 0.65468(16) 0.0377(4) Uani 1 1 d . . . . .
H3 H 0.731909 0.349919 0.672482 0.057 Uiso 1 1 calc R U . . .
N1 N 0.68309(18) 0.46456(10) 0.4669(2) 0.0304(4) Uani 1 1 d . . . . .
N2 N 0.6952(2) 0.21041(11) 0.4837(2) 0.0386(5) Uani 1 1 d . . . . .
H2 H 0.702455 0.230229 0.569333 0.046 Uiso 1 1 calc R U . . .
C1 C 0.8219(3) 0.55912(17) 0.6724(3) 0.0545(7) Uani 1 1 d . . . . .
H1A H 0.812465 0.532747 0.755956 0.082 Uiso 1 1 calc R U . . .
H1B H 0.822625 0.614250 0.688145 0.082 Uiso 1 1 calc R U . . .
H1C H 0.904275 0.543702 0.667039 0.082 Uiso 1 1 calc R U . . .
C2 C 0.7082(3) 0.53854(13) 0.5272(3) 0.0374(5) Uani 1 1 d . . . . .
C3 C 0.6039(3) 0.58345(14) 0.4314(3) 0.0461(6) Uani 1 1 d . . . . .
H3A H 0.594073 0.636425 0.443194 0.055 Uiso 1 1 calc R U . . .
C4 C 0.5139(3) 0.53706(14) 0.3124(3) 0.0423(6) Uani 1 1 d . . . . .
H4 H 0.435162 0.553147 0.232834 0.051 Uiso 1 1 calc R U . . .
C5 C 0.5663(2) 0.46327(13) 0.3382(2) 0.0314(5) Uani 1 1 d . . . . .
C6 C 0.5383(2) 0.38361(12) 0.2861(2) 0.0277(4) Uani 1 1 d . . . . .
C7 C 0.6390(2) 0.33789(12) 0.3822(2) 0.0251(4) Uani 1 1 d . . . . .
C8 C 0.7470(2) 0.38849(12) 0.5019(2) 0.0249(4) Uani 1 1 d . . . . .
C9 C 0.8729(2) 0.39001(14) 0.4679(3) 0.0353(5) Uani 1 1 d . . . . .
C10 C 0.6578(2) 0.25450(12) 0.3591(2) 0.0248(4) Uani 1 1 d . . . . .
C11 C 0.8631(3) 0.12132(19) 0.5211(3) 0.0624(9) Uani 1 1 d . . . . .
H11A H 0.890972 0.146551 0.449336 0.094 Uiso 1 1 calc R U . . .
H11B H 0.882221 0.066752 0.523888 0.094 Uiso 1 1 calc R U . . .
H11C H 0.910414 0.143258 0.621001 0.094 Uiso 1 1 calc R U . . .
C12 C 0.4161(2) 0.35965(14) 0.1556(2) 0.0347(5) Uani 1 1 d . . . . .
C13 C 0.3435(2) 0.29544(15) 0.1641(3) 0.0417(6) Uani 1 1 d . . . . .
H13 H 0.374189 0.265093 0.252223 0.050 Uiso 1 1 calc R U . . .
C14 C 0.2257(3) 0.27611(19) 0.0426(4) 0.0585(8) Uani 1 1 d . . . . .
H14 H 0.177309 0.232932 0.049506 0.070 Uiso 1 1 calc R U . . .
C15 C 0.1794(3) 0.3204(2) -0.0888(4) 0.0723(10) Uani 1 1 d . . . . .
H15 H 0.099576 0.307451 -0.170135 0.087 Uiso 1 1 calc R U . . .
C16 C 0.2514(4) 0.3832(3) -0.0987(4) 0.0814(12) Uani 1 1 d . . . . .
H16 H 0.221174 0.412491 -0.188140 0.098 Uiso 1 1 calc R U . . .
C17 C 0.3683(3) 0.4039(2) 0.0220(3) 0.0614(9) Uani 1 1 d . . . . .
H17 H 0.415456 0.447534 0.014404 0.074 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 C9 1.326(3) . ?
F2 C9 1.326(3) . ?
F3 C9 1.331(3) . ?
O1 N2 1.386(2) . ?
O1 C11 1.431(4) . ?
O2 C10 1.236(2) . ?
O3 H3 0.8200 . ?
O3 C8 1.383(2) . ?
N1 C2 1.378(3) . ?
N1 C5 1.368(3) . ?
N1 C8 1.457(3) . ?
N2 H2 0.8600 . ?
N2 C10 1.329(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.483(3) . ?
C2 C3 1.375(4) . ?
C3 H3A 0.9300 . ?
C3 C4 1.411(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.374(3) . ?
C5 C6 1.448(3) . ?
C6 C7 1.362(3) . ?
C6 C12 1.470(3) . ?
C7 C8 1.538(3) . ?
C7 C10 1.478(3) . ?
C8 C9 1.538(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.382(4) . ?
C12 C17 1.394(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.381(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.378(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.364(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.377(4) . ?
C17 H17 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
N2 O1 C11 109.9(2) . . ?
C8 O3 H3 109.5 . . ?
C2 N1 C8 137.53(19) . . ?
C5 N1 C2 110.25(19) . . ?
C5 N1 C8 112.21(17) . . ?
O1 N2 H2 120.2 . . ?
C10 N2 O1 119.67(18) . . ?
C10 N2 H2 120.2 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
N1 C2 C1 124.1(2) . . ?
C3 C2 N1 105.6(2) . . ?
C3 C2 C1 130.1(2) . . ?
C2 C3 H3A 125.1 . . ?
C2 C3 C4 109.8(2) . . ?
C4 C3 H3A 125.1 . . ?
C3 C4 H4 127.0 . . ?
C5 C4 C3 105.9(2) . . ?
C5 C4 H4 127.0 . . ?
N1 C5 C4 108.4(2) . . ?
N1 C5 C6 108.33(18) . . ?
C4 C5 C6 143.0(2) . . ?
C5 C6 C12 123.35(19) . . ?
C7 C6 C5 108.35(18) . . ?
C7 C6 C12 128.2(2) . . ?
C6 C7 C8 109.97(17) . . ?
C6 C7 C10 125.65(18) . . ?
C10 C7 C8 123.33(17) . . ?
O3 C8 N1 114.23(17) . . ?
O3 C8 C7 118.89(17) . . ?
O3 C8 C9 104.44(17) . . ?
N1 C8 C7 100.69(15) . . ?
N1 C8 C9 108.84(17) . . ?
C9 C8 C7 109.57(17) . . ?
F1 C9 F2 107.0(2) . . ?
F1 C9 F3 106.46(19) . . ?
F1 C9 C8 112.83(19) . . ?
F2 C9 F3 107.3(2) . . ?
F2 C9 C8 111.44(18) . . ?
F3 C9 C8 111.50(19) . . ?
O2 C10 N2 122.53(19) . . ?
O2 C10 C7 121.89(18) . . ?
N2 C10 C7 115.54(17) . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C6 121.4(2) . . ?
C13 C12 C17 118.7(2) . . ?
C17 C12 C6 119.9(2) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.4(3) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.5(3) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 120.3 . . ?
C16 C15 C14 119.5(3) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 H16 119.6 . . ?
C15 C16 C17 120.9(3) . . ?
C17 C16 H16 119.6 . . ?
C12 C17 H17 119.9 . . ?
C16 C17 C12 120.2(3) . . ?
C16 C17 H17 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
O1 N2 C10 O2 1.1(3) . . . . ?
O1 N2 C10 C7 -176.44(19) . . . . ?
O3 C8 C9 F1 -49.8(2) . . . . ?
O3 C8 C9 F2 -170.26(19) . . . . ?
O3 C8 C9 F3 69.9(2) . . . . ?
N1 C2 C3 C4 0.4(3) . . . . ?
N1 C5 C6 C7 -0.8(3) . . . . ?
N1 C5 C6 C12 176.1(2) . . . . ?
N1 C8 C9 F1 72.6(2) . . . . ?
N1 C8 C9 F2 -47.9(2) . . . . ?
N1 C8 C9 F3 -167.69(18) . . . . ?
C1 C2 C3 C4 -175.5(3) . . . . ?
C2 N1 C5 C4 0.3(3) . . . . ?
C2 N1 C5 C6 -175.35(19) . . . . ?
C2 N1 C8 O3 45.3(3) . . . . ?
C2 N1 C8 C7 174.0(3) . . . . ?
C2 N1 C8 C9 -70.9(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 N1 -0.1(3) . . . . ?
C3 C4 C5 C6 173.1(3) . . . . ?
C4 C5 C6 C7 -174.0(3) . . . . ?
C4 C5 C6 C12 2.9(5) . . . . ?
C5 N1 C2 C1 175.8(2) . . . . ?
C5 N1 C2 C3 -0.4(3) . . . . ?
C5 N1 C8 O3 -135.29(19) . . . . ?
C5 N1 C8 C7 -6.7(2) . . . . ?
C5 N1 C8 C9 108.5(2) . . . . ?
C5 C6 C7 C8 -3.5(2) . . . . ?
C5 C6 C7 C10 -172.0(2) . . . . ?
C5 C6 C12 C13 -134.1(3) . . . . ?
C5 C6 C12 C17 43.2(4) . . . . ?
C6 C7 C8 O3 131.6(2) . . . . ?
C6 C7 C8 N1 6.0(2) . . . . ?
C6 C7 C8 C9 -108.5(2) . . . . ?
C6 C7 C10 O2 43.4(3) . . . . ?
C6 C7 C10 N2 -139.0(2) . . . . ?
C6 C12 C13 C14 177.0(2) . . . . ?
C6 C12 C17 C16 -177.8(3) . . . . ?
C7 C6 C12 C13 42.2(4) . . . . ?
C7 C6 C12 C17 -140.5(3) . . . . ?
C7 C8 C9 F1 -178.22(18) . . . . ?
C7 C8 C9 F2 61.4(2) . . . . ?
C7 C8 C9 F3 -58.5(2) . . . . ?
C8 N1 C2 C1 -4.8(4) . . . . ?
C8 N1 C2 C3 178.9(2) . . . . ?
C8 N1 C5 C4 -179.21(19) . . . . ?
C8 N1 C5 C6 5.1(2) . . . . ?
C8 C7 C10 O2 -123.8(2) . . . . ?
C8 C7 C10 N2 53.8(3) . . . . ?
C10 C7 C8 O3 -59.5(3) . . . . ?
C10 C7 C8 N1 174.95(18) . . . . ?
C10 C7 C8 C9 60.4(2) . . . . ?
C11 O1 N2 C10 96.0(3) . . . . ?
C12 C6 C7 C8 179.8(2) . . . . ?
C12 C6 C7 C10 11.2(4) . . . . ?
C12 C13 C14 C15 0.3(5) . . . . ?
C13 C12 C17 C16 -0.4(5) . . . . ?
C13 C14 C15 C16 0.6(6) . . . . ?
C14 C15 C16 C17 -1.3(6) . . . . ?
C15 C16 C17 C12 1.3(6) . . . . ?
C17 C12 C13 C14 -0.3(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 2.315
_oxdiff_exptl_absorpt_empirical_full_min 0.578
