# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2025

####################################################################### 
# 
# 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_exp_351
_database_code_depnum_ccdc_archive 'CCDC 2297091'
loop_
_audit_author_name
_audit_author_address
'Alexey Barkov'
;Ural Federal University
Russia
;
_audit_update_record             
;
2023-09-24 deposited with the CCDC.	2025-10-29 downloaded from the CCDC.
;
_audit_creation_date             2023-04-28
_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         'C15 H11 F3 N2 O6'
_chemical_formula_sum            'C15 H11 F3 N2 O6'
_chemical_formula_weight         372.26
_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 0.0033 0.0016 '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 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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                   7.6176(7)
_cell_length_b                   11.1985(9)
_cell_length_c                   18.9787(18)
_cell_angle_alpha                90
_cell_angle_beta                 95.657(10)
_cell_angle_gamma                90
_cell_volume                     1611.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2540
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      23.5470
_cell_measurement_theta_min      4.0270
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.937
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.0656
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.879
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12656
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.478
_diffrn_reflns_theta_min         3.713
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 16.5253
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.990
_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     68.00  93.00   1.00   60.00    --   21.29  10.00  48.00   25
  2  ω     -2.00  23.00   1.00   60.00    --   21.29  10.00  48.00   25
  3  ω     -4.00  21.00   1.00   60.00    --   21.29 -10.00-125.00   25
  4  ω    -94.00  39.00   1.00   60.00    --  -22.70 -10.00-125.00  133
  5  ω      3.00  90.00   1.00   60.00    --   21.29  57.00-120.00   87
  6  ω    -97.00 -55.00   1.00   60.00    --  -22.70-178.00  30.00   42
  7  ω    -46.00 -21.00   1.00   60.00    --  -22.70  10.00  48.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1880
_reflns_number_total             4307
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.007(3)
_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   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4307
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1495
_refine_ls_R_factor_gt           0.0643
_refine_ls_restrained_S_all      1.013
_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)+(0.1008P)²+0.0865P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1690
_refine_ls_wR_factor_ref         0.2370
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C15) \\sim Ueq, Uanis(C15A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3. Others
 Fixed Sof: H14A(0.5) H14B(0.5) H14C(0.5) H14D(0.5) C15(0.5) H15A(0.5)
 H15B(0.5) H15C(0.5) C15A(0.5) H15D(0.5) H15E(0.5) H15F(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C14(H14C,H14D)
4.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C15A(H15D,H15E,H15F)
;
_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
O3 O -0.0019(3) 0.61650(19) 0.43152(12) 0.0697(6) Uani 1 1 d . . . . .
O4 O 0.0989(3) 0.6359(2) 0.32569(12) 0.0720(6) Uani 1 1 d . . . . .
O2 O 0.7856(3) 0.37964(19) 0.40904(15) 0.0819(8) Uani 1 1 d . . . . .
O1 O 0.9795(3) 0.1927(2) 0.43658(15) 0.0834(8) Uani 1 1 d . . . . .
N1 N 0.2440(3) 0.4402(2) 0.46620(14) 0.0590(7) Uani 1 1 d . . . . .
N006 N 0.3691(4) -0.0785(3) 0.39598(16) 0.0741(8) Uani 1 1 d . . . . .
F3 F 0.3144(4) 0.4991(3) 0.25084(12) 0.1259(10) Uani 1 1 d . . . . .
F2 F 0.4928(4) 0.6187(2) 0.30241(16) 0.1365(12) Uani 1 1 d . . . . .
F1 F 0.5705(4) 0.4413(3) 0.28220(14) 0.1382(12) Uani 1 1 d . . . . .
O6 O 0.3812(4) -0.1856(3) 0.40907(17) 0.1041(10) Uani 1 1 d . . . . .
O5 O 0.2298(3) -0.0299(2) 0.3757(2) 0.1153(12) Uani 1 1 d . . . . .
C2 C 0.2429(4) 0.5035(3) 0.40535(15) 0.0543(7) Uani 1 1 d . . . . .
C7 C 0.6616(4) 0.1883(2) 0.41447(15) 0.0551(7) Uani 1 1 d . . . . .
C13 C 0.1001(4) 0.5900(2) 0.38956(16) 0.0559(7) Uani 1 1 d . . . . .
C11 C 0.5271(4) -0.0044(3) 0.40641(15) 0.0573(7) Uani 1 1 d . . . . .
C4 C 0.4781(4) 0.3784(3) 0.41659(16) 0.0580(8) Uani 1 1 d . . . . .
C3 C 0.3904(4) 0.4663(3) 0.37248(15) 0.0570(7) Uani 1 1 d . . . . .
C12 C 0.5107(4) 0.1173(3) 0.40417(16) 0.0566(7) Uani 1 1 d . . . . .
C6 C 0.6513(4) 0.3183(3) 0.41197(16) 0.0610(8) Uani 1 1 d . . . . .
C8 C 0.8289(4) 0.1310(3) 0.42601(16) 0.0614(8) Uani 1 1 d . . . . .
C5 C 0.3811(4) 0.3635(3) 0.47341(18) 0.0613(8) Uani 1 1 d . . . . .
C10 C 0.6899(4) -0.0614(3) 0.41788(17) 0.0653(8) Uani 1 1 d . . . . .
C9 C 0.8398(4) 0.0075(3) 0.42744(18) 0.0678(9) Uani 1 1 d . . . . .
C1 C 0.4448(5) 0.5072(4) 0.3034(2) 0.0773(10) Uani 1 1 d . . . . .
C14 C -0.0352(5) 0.7262(4) 0.3049(2) 0.0892(11) Uani 1 1 d . . . . .
H14A H -0.036633 0.787168 0.341170 0.107 Uiso 0.5 1 calc R U P A 1
H14B H -0.151228 0.690028 0.297600 0.107 Uiso 0.5 1 calc R U P A 1
H14C H -0.145398 0.705537 0.323482 0.107 Uiso 0.5 1 calc R U P B 2
H14D H 0.002727 0.803548 0.323742 0.107 Uiso 0.5 1 calc R U P B 2
C15 C 0.015(2) 0.7780(14) 0.2385(8) 0.116(5) Uani 0.5 1 d . U P C 1
H15A H 0.129015 0.815041 0.246971 0.174 Uiso 0.5 1 calc R U P C 1
H15B H -0.070423 0.836602 0.221319 0.174 Uiso 0.5 1 calc R U P C 1
H15C H 0.020119 0.715940 0.203780 0.174 Uiso 0.5 1 calc R U P C 1
C15A C -0.059(2) 0.7304(18) 0.2284(10) 0.155(7) Uani 0.5 1 d . U P C 2
H15D H 0.050259 0.751697 0.210554 0.232 Uiso 0.5 1 calc R U P C 2
H15E H -0.147296 0.788876 0.213476 0.232 Uiso 0.5 1 calc R U P C 2
H15F H -0.096443 0.653473 0.210274 0.232 Uiso 0.5 1 calc R U P C 2
H1 H 0.950(5) 0.279(4) 0.4242(19) 0.086(11) Uiso 1 1 d . . . . .
H12 H 0.386(4) 0.157(3) 0.3957(16) 0.065(8) Uiso 1 1 d . . . . .
H1A H 0.181(4) 0.461(3) 0.4967(18) 0.072(10) Uiso 1 1 d . . . . .
H5 H 0.410(4) 0.313(3) 0.5167(18) 0.073(9) Uiso 1 1 d . . . . .
H9 H 0.962(6) -0.029(4) 0.432(2) 0.112(13) Uiso 1 1 d . . . . .
H10 H 0.701(5) -0.150(3) 0.416(2) 0.096(12) 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
O3 C13 1.203(3) . ?
O4 C13 1.316(3) . ?
O4 C14 1.463(4) . ?
O2 C6 1.238(3) . ?
O1 C8 1.337(3) . ?
O1 H1 1.01(4) . ?
N1 C2 1.354(4) . ?
N1 C5 1.349(4) . ?
N1 H1A 0.82(3) . ?
N006 O6 1.227(4) . ?
N006 O5 1.220(4) . ?
N006 C11 1.459(4) . ?
F3 C1 1.340(4) . ?
F2 C1 1.301(4) . ?
F1 C1 1.304(4) . ?
C2 C13 1.465(4) . ?
C2 C3 1.401(4) . ?
C7 C12 1.395(4) . ?
C7 C6 1.458(4) . ?
C7 C8 1.424(4) . ?
C11 C12 1.369(4) . ?
C11 C10 1.392(4) . ?
C4 C3 1.416(4) . ?
C4 C6 1.492(4) . ?
C4 C5 1.376(4) . ?
C3 C1 1.485(4) . ?
C12 H12 1.05(3) . ?
C8 C9 1.386(5) . ?
C5 H5 1.01(3) . ?
C10 C9 1.375(5) . ?
C10 H10 0.99(4) . ?
C9 H9 1.01(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C14 H14D 0.9700 . ?
C14 C15 1.473(13) . ?
C14 C15A 1.448(19) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C15A H15D 0.9600 . ?
C15A H15E 0.9600 . ?
C15A H15F 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
C13 O4 C14 117.4(2) . . ?
C8 O1 H1 107(2) . . ?
C2 N1 H1A 120(2) . . ?
C5 N1 C2 111.1(2) . . ?
C5 N1 H1A 127(2) . . ?
O6 N006 C11 118.9(3) . . ?
O5 N006 O6 123.0(3) . . ?
O5 N006 C11 118.0(3) . . ?
N1 C2 C13 117.5(2) . . ?
N1 C2 C3 106.6(3) . . ?
C3 C2 C13 135.8(3) . . ?
C12 C7 C6 121.6(3) . . ?
C12 C7 C8 118.5(3) . . ?
C8 C7 C6 119.9(3) . . ?
O3 C13 O4 124.5(3) . . ?
O3 C13 C2 122.9(3) . . ?
O4 C13 C2 112.6(2) . . ?
C12 C11 N006 119.4(3) . . ?
C12 C11 C10 122.5(3) . . ?
C10 C11 N006 118.1(3) . . ?
C3 C4 C6 130.4(3) . . ?
C5 C4 C3 106.8(2) . . ?
C5 C4 C6 122.5(3) . . ?
C2 C3 C4 107.2(2) . . ?
C2 C3 C1 127.4(3) . . ?
C4 C3 C1 125.4(3) . . ?
C7 C12 H12 119.9(16) . . ?
C11 C12 C7 119.5(3) . . ?
C11 C12 H12 120.6(16) . . ?
O2 C6 C7 120.9(3) . . ?
O2 C6 C4 119.4(3) . . ?
C7 C6 C4 119.6(3) . . ?
O1 C8 C7 122.1(3) . . ?
O1 C8 C9 117.6(3) . . ?
C9 C8 C7 120.2(3) . . ?
N1 C5 C4 108.3(3) . . ?
N1 C5 H5 123.3(17) . . ?
C4 C5 H5 128.0(17) . . ?
C11 C10 H10 122(2) . . ?
C9 C10 C11 118.6(3) . . ?
C9 C10 H10 119(2) . . ?
C8 C9 H9 117(2) . . ?
C10 C9 C8 120.7(3) . . ?
C10 C9 H9 122(2) . . ?
F3 C1 C3 112.7(3) . . ?
F2 C1 F3 104.0(3) . . ?
F2 C1 F1 108.8(3) . . ?
F2 C1 C3 114.4(3) . . ?
F1 C1 F3 104.1(3) . . ?
F1 C1 C3 112.1(3) . . ?
O4 C14 H14A 110.6 . . ?
O4 C14 H14B 110.6 . . ?
O4 C14 H14C 110.1 . . ?
O4 C14 H14D 110.1 . . ?
O4 C14 C15 105.6(6) . . ?
H14A C14 H14B 108.8 . . ?
H14C C14 H14D 108.4 . . ?
C15 C14 H14A 110.6 . . ?
C15 C14 H14B 110.6 . . ?
C15A C14 O4 108.0(8) . . ?
C15A C14 H14C 110.1 . . ?
C15A C14 H14D 110.1 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C15A H15D 109.5 . . ?
C14 C15A H15E 109.5 . . ?
C14 C15A H15F 109.5 . . ?
H15D C15A H15E 109.5 . . ?
H15D C15A H15F 109.5 . . ?
H15E C15A H15F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C8 C9 C10 179.2(3) . . . . ?
N1 C2 C13 O3 8.9(4) . . . . ?
N1 C2 C13 O4 -172.3(2) . . . . ?
N1 C2 C3 C4 0.0(3) . . . . ?
N1 C2 C3 C1 178.4(3) . . . . ?
N006 C11 C12 C7 179.7(3) . . . . ?
N006 C11 C10 C9 179.7(3) . . . . ?
O6 N006 C11 C12 -168.5(3) . . . . ?
O6 N006 C11 C10 11.9(4) . . . . ?
O5 N006 C11 C12 10.2(4) . . . . ?
O5 N006 C11 C10 -169.4(3) . . . . ?
C2 N1 C5 C4 1.8(4) . . . . ?
C2 C3 C1 F3 -52.2(5) . . . . ?
C2 C3 C1 F2 66.4(5) . . . . ?
C2 C3 C1 F1 -169.2(3) . . . . ?
C7 C8 C9 C10 -0.1(5) . . . . ?
C13 O4 C14 C15 169.2(7) . . . . ?
C13 O4 C14 C15A -158.2(9) . . . . ?
C13 C2 C3 C4 179.5(3) . . . . ?
C13 C2 C3 C1 -2.1(6) . . . . ?
C11 C10 C9 C8 0.3(5) . . . . ?
C4 C3 C1 F3 126.0(3) . . . . ?
C4 C3 C1 F2 -115.5(4) . . . . ?
C4 C3 C1 F1 8.9(5) . . . . ?
C3 C2 C13 O3 -170.5(3) . . . . ?
C3 C2 C13 O4 8.3(5) . . . . ?
C3 C4 C6 O2 54.3(5) . . . . ?
C3 C4 C6 C7 -128.7(3) . . . . ?
C3 C4 C5 N1 -1.7(4) . . . . ?
C12 C7 C6 O2 -167.5(3) . . . . ?
C12 C7 C6 C4 15.5(4) . . . . ?
C12 C7 C8 O1 -179.7(3) . . . . ?
C12 C7 C8 C9 -0.5(4) . . . . ?
C12 C11 C10 C9 0.1(5) . . . . ?
C6 C7 C12 C11 179.5(3) . . . . ?
C6 C7 C8 O1 1.7(4) . . . . ?
C6 C7 C8 C9 -179.1(3) . . . . ?
C6 C4 C3 C2 -172.5(3) . . . . ?
C6 C4 C3 C1 9.1(5) . . . . ?
C6 C4 C5 N1 172.4(3) . . . . ?
C8 C7 C12 C11 0.9(4) . . . . ?
C8 C7 C6 O2 11.0(5) . . . . ?
C8 C7 C6 C4 -166.0(3) . . . . ?
C5 N1 C2 C13 179.3(3) . . . . ?
C5 N1 C2 C3 -1.1(3) . . . . ?
C5 C4 C3 C2 1.0(3) . . . . ?
C5 C4 C3 C1 -177.4(3) . . . . ?
C5 C4 C6 O2 -118.3(4) . . . . ?
C5 C4 C6 C7 58.7(4) . . . . ?
C10 C11 C12 C7 -0.7(5) . . . . ?
C14 O4 C13 O3 0.6(5) . . . . ?
C14 O4 C13 C2 -178.2(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# 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_exp_411
_database_code_depnum_ccdc_archive 'CCDC 2454280'
loop_
_audit_author_name
_audit_author_address
'Alexey Barkov'
;Ural Federal University
Russia
;
_audit_update_record             
;
2025-05-27 deposited with the CCDC.	2025-10-29 downloaded from the CCDC.
;
_audit_creation_date             2023-09-22
_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 H14 F3 N O4'
_chemical_formula_sum            'C17 H14 F3 N O4'
_chemical_formula_weight         353.29
_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 0.0033 0.0016 '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 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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                   7.7224(7)
_cell_length_b                   14.8067(13)
_cell_length_c                   15.0191(11)
_cell_angle_alpha                107.418(7)
_cell_angle_beta                 97.252(7)
_cell_angle_gamma                95.632(7)
_cell_volume                     1608.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2319
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      22.4020
_cell_measurement_theta_min      3.6360
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.942
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87235
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_av_unetI/netI     0.1365
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15647
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.564
_diffrn_reflns_theta_min         3.670
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 16.5253
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     56.00  86.00   1.00   10.00    --   21.29-169.00  11.00   30
  2  ω    -72.00 -46.00   1.00   10.00    --  -22.70 116.00-115.00   26
  3  ω    -23.00   7.00   1.00   10.00    --  -22.70 116.00-115.00   30
  4  ω    -88.00 -63.00   1.00   10.00    --  -22.70 169.00  28.00   25
  5  ω     -7.00  20.00   1.00   10.00    --   21.29-116.00 155.00   27
  6  ω    -49.00  43.00   1.00   10.00    --   21.29 -38.00   0.00   92
  7  ω     46.00  71.00   1.00   10.00    --   21.29-116.00 155.00   25
  8  ω      2.00  30.00   1.00   10.00    --   21.29  77.00  30.00   28
  9  ω    -97.00 -39.00   1.00   10.00    --  -22.70-178.00 120.00   58
 10  ω    -93.00  -1.00   1.00   10.00    --  -22.70 -38.00  90.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2939
_reflns_number_total             8513
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     482
_refine_ls_number_reflns         8513
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2098
_refine_ls_R_factor_gt           0.0743
_refine_ls_restrained_S_all      0.959
_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)+(0.0937P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1746
_refine_ls_wR_factor_ref         0.2658
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C15A(H15C,H15D)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C10(H10), C13(H13), C12(H12), C10A(H10A), C11(H11), C14A(H14A),
 C11A(H11A), C12A(H12A), C13A(H13A)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C16A(H16D,H16E,H16F)
2.d Idealised tetrahedral OH refined as rotating group:
 O4A(H4A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F2 F 0.5519(4) 0.11629(18) 0.83006(19) 0.0912(9) Uani 1 1 d . . . . .
O2 O 0.6296(4) 0.29725(19) 0.84809(18) 0.0624(7) Uani 1 1 d . . . . .
F1 F 0.5383(4) -0.01898(19) 0.7281(2) 0.0960(9) Uani 1 1 d . . . . .
F2A F 0.1888(4) 0.72751(19) 0.57391(19) 0.0920(9) Uani 1 1 d . . . . .
F3 F 0.7847(4) 0.0525(2) 0.81180(19) 0.0920(9) Uani 1 1 d . . . . .
O1 O 0.5475(4) 0.35305(19) 0.72876(19) 0.0686(8) Uani 1 1 d . . . . .
O2A O 0.5177(4) 0.7334(2) 0.8334(2) 0.0716(8) Uani 1 1 d . . . . .
O3A O 0.2475(4) 0.5932(2) 0.4182(2) 0.0773(9) Uani 1 1 d . . . . .
N1 N 0.6675(4) 0.2109(2) 0.6050(2) 0.0496(8) Uani 1 1 d . . . . .
F3A F 0.4668(4) 0.7459(2) 0.5792(3) 0.1093(11) Uani 1 1 d . . . . .
O3 O 0.8031(5) -0.0775(2) 0.6217(2) 0.0903(11) Uani 1 1 d . . . . .
F1A F 0.3488(5) 0.7850(2) 0.7072(2) 0.1288(14) Uani 1 1 d . . . . .
O4 O 0.8626(5) -0.2111(2) 0.4871(2) 0.0886(11) Uani 1 1 d . . . . .
O1A O 0.4816(5) 0.5944(2) 0.8626(2) 0.0914(11) Uani 1 1 d . . . . .
O4A O 0.1282(6) 0.4831(2) 0.2543(2) 0.0984(12) Uani 1 1 d . . . . .
H4A H 0.146663 0.534484 0.296885 0.148 Uiso 1 1 calc R U . . .
N1A N 0.3828(5) 0.4961(2) 0.6775(2) 0.0622(9) Uani 1 1 d . . . . .
C2 C 0.6430(5) 0.2037(2) 0.6919(2) 0.0453(8) Uani 1 1 d . . . . .
C3 C 0.6685(4) 0.1108(2) 0.6910(2) 0.0437(8) Uani 1 1 d . . . . .
C4 C 0.7128(5) 0.0634(2) 0.6001(2) 0.0460(9) Uani 1 1 d . . . . .
C1 C 0.6007(5) 0.2908(3) 0.7581(3) 0.0490(9) Uani 1 1 d . . . . .
C2A C 0.4012(5) 0.5942(3) 0.7066(3) 0.0510(9) Uani 1 1 d . . . . .
C4A C 0.2949(5) 0.5349(3) 0.5486(3) 0.0514(9) Uani 1 1 d . . . . .
C3A C 0.3472(5) 0.6209(3) 0.6271(3) 0.0508(9) Uani 1 1 d . . . . .
C5 C 0.7090(5) 0.1281(3) 0.5498(3) 0.0502(9) Uani 1 1 d . . . . .
C6 C 0.7639(5) -0.0321(3) 0.5635(3) 0.0523(9) Uani 1 1 d . . . . .
C6A C 0.2360(5) 0.5225(3) 0.4489(3) 0.0535(10) Uani 1 1 d . . . . .
C8 C 0.8288(5) -0.1594(3) 0.4317(3) 0.0537(10) Uani 1 1 d . . . . .
C9 C 0.8520(5) -0.2023(3) 0.3323(3) 0.0541(10) Uani 1 1 d . . . . .
C5A C 0.3205(6) 0.4603(3) 0.5839(3) 0.0621(11) Uani 1 1 d . . . . .
C17 C 0.6376(6) 0.0661(3) 0.7654(3) 0.0562(10) Uani 1 1 d . . . . .
C7 C 0.7754(5) -0.0713(3) 0.4671(3) 0.0558(10) Uani 1 1 d . . . . .
C9A C 0.0470(5) 0.3184(3) 0.2204(3) 0.0584(10) Uani 1 1 d . . . . .
C7A C 0.1673(6) 0.4289(3) 0.3852(3) 0.0603(11) Uani 1 1 d . . . . .
C1A C 0.4702(5) 0.6401(3) 0.8081(3) 0.0565(10) Uani 1 1 d . . . . .
C8A C 0.1163(5) 0.4124(3) 0.2914(3) 0.0598(10) Uani 1 1 d . . . . .
C14 C 0.8963(5) -0.2940(3) 0.3017(3) 0.0637(11) Uani 1 1 d . . . . .
H14 H 0.914591 -0.327421 0.344772 0.076 Uiso 1 1 calc R U . . .
C17A C 0.3384(7) 0.7196(3) 0.6229(3) 0.0673(12) Uani 1 1 d . . . . .
C10 C 0.8299(6) -0.1533(3) 0.2665(3) 0.0663(12) Uani 1 1 d . . . . .
H10 H 0.800618 -0.091729 0.285276 0.080 Uiso 1 1 calc R U . . .
C15 C 0.5890(6) 0.3837(3) 0.9154(3) 0.0650(11) Uani 1 1 d . . . . .
H15A H 0.545691 0.368044 0.967657 0.078 Uiso 1 1 calc R U . . .
H15B H 0.497486 0.409749 0.884499 0.078 Uiso 1 1 calc R U . . .
C13 C 0.9137(6) -0.3366(3) 0.2082(4) 0.0757(13) Uani 1 1 d . . . . .
H13 H 0.941388 -0.398484 0.188810 0.091 Uiso 1 1 calc R U . . .
C12 C 0.8903(6) -0.2878(4) 0.1443(3) 0.0771(14) Uani 1 1 d . . . . .
H12 H 0.900793 -0.316701 0.081488 0.093 Uiso 1 1 calc R U . . .
C10A C -0.0354(6) 0.3125(3) 0.1303(3) 0.0740(13) Uani 1 1 d . . . . .
H10A H -0.047588 0.368543 0.115588 0.089 Uiso 1 1 calc R U . . .
C16 C 0.7510(6) 0.4564(3) 0.9520(3) 0.0822(14) Uani 1 1 d . . . . .
H16A H 0.787564 0.475806 0.900904 0.123 Uiso 1 1 calc R U . . .
H16B H 0.843625 0.428962 0.978887 0.123 Uiso 1 1 calc R U . . .
H16C H 0.725967 0.510946 0.999563 0.123 Uiso 1 1 calc R U . . .
C11 C 0.8510(6) -0.1952(4) 0.1735(3) 0.0766(13) Uani 1 1 d . . . . .
H11 H 0.838849 -0.161140 0.130691 0.092 Uiso 1 1 calc R U . . .
C15A C 0.5850(7) 0.7828(3) 0.9320(3) 0.0765(13) Uani 1 1 d . . . . .
H15C H 0.700619 0.766784 0.949163 0.092 Uiso 1 1 calc R U . . .
H15D H 0.506602 0.764622 0.971326 0.092 Uiso 1 1 calc R U . . .
C14A C 0.0637(6) 0.2331(3) 0.2404(3) 0.0777(13) Uani 1 1 d . . . . .
H14A H 0.118181 0.234670 0.299777 0.093 Uiso 1 1 calc R U . . .
C11A C -0.0989(7) 0.2262(4) 0.0628(4) 0.0872(15) Uani 1 1 d . . . . .
H11A H -0.152066 0.223999 0.002977 0.105 Uiso 1 1 calc R U . . .
C12A C -0.0838(7) 0.1426(4) 0.0838(4) 0.0960(17) Uani 1 1 d . . . . .
H12A H -0.129629 0.083997 0.038741 0.115 Uiso 1 1 calc R U . . .
C16A C 0.5964(7) 0.8883(3) 0.9460(4) 0.0947(16) Uani 1 1 d . . . . .
H16D H 0.668285 0.904755 0.903894 0.142 Uiso 1 1 calc R U . . .
H16E H 0.647956 0.923540 1.010209 0.142 Uiso 1 1 calc R U . . .
H16F H 0.480207 0.904022 0.932831 0.142 Uiso 1 1 calc R U . . .
C13A C -0.0010(8) 0.1462(4) 0.1716(4) 0.0999(18) Uani 1 1 d . . . . .
H13A H 0.011919 0.089556 0.184948 0.120 Uiso 1 1 calc R U . . .
H1 H 0.655(6) 0.268(3) 0.590(3) 0.095(15) Uiso 1 1 d . . . . .
H1A H 0.436(8) 0.464(5) 0.724(5) 0.16(2) Uiso 1 1 d . . . . .
H7 H 0.748(5) -0.037(3) 0.427(3) 0.066(12) Uiso 1 1 d . . . . .
H5 H 0.740(5) 0.124(3) 0.482(3) 0.063(11) Uiso 1 1 d . . . . .
H5A H 0.301(5) 0.393(3) 0.548(3) 0.061(11) Uiso 1 1 d . . . . .
H7A H 0.167(6) 0.377(3) 0.411(3) 0.088(15) Uiso 1 1 d . . . . .
H3 H 0.836(8) -0.163(5) 0.560(5) 0.15(2) 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
F2 C17 1.327(4) . ?
O2 C1 1.314(4) . ?
O2 C15 1.464(4) . ?
F1 C17 1.330(5) . ?
F2A C17A 1.324(5) . ?
F3 C17 1.321(4) . ?
O1 C1 1.218(4) . ?
O2A C1A 1.319(5) . ?
O2A C15A 1.442(5) . ?
O3A C6A 1.263(4) . ?
N1 C2 1.375(5) . ?
N1 C5 1.352(4) . ?
N1 H1 0.94(5) . ?
F3A C17A 1.344(5) . ?
O3 C6 1.278(4) . ?
O3 H3 1.39(7) . ?
F1A C17A 1.331(5) . ?
O4 C8 1.308(4) . ?
O4 H3 1.17(7) . ?
O1A C1A 1.208(4) . ?
O4A H4A 0.8200 . ?
O4A C8A 1.325(5) . ?
N1A C2A 1.373(5) . ?
N1A C5A 1.349(5) . ?
N1A H1A 1.02(6) . ?
C2 C3 1.404(4) . ?
C2 C1 1.469(5) . ?
C3 C4 1.437(5) . ?
C3 C17 1.492(5) . ?
C4 C5 1.387(5) . ?
C4 C6 1.469(5) . ?
C2A C3A 1.394(5) . ?
C2A C1A 1.474(5) . ?
C4A C3A 1.433(5) . ?
C4A C6A 1.460(5) . ?
C4A C5A 1.382(5) . ?
C3A C17A 1.490(5) . ?
C5 H5 1.07(4) . ?
C6 C7 1.407(5) . ?
C6A C7A 1.432(6) . ?
C8 C9 1.478(5) . ?
C8 C7 1.379(5) . ?
C9 C14 1.388(5) . ?
C9 C10 1.394(6) . ?
C5A H5A 0.96(4) . ?
C7 H7 0.92(4) . ?
C9A C8A 1.477(5) . ?
C9A C10A 1.395(6) . ?
C9A C14A 1.396(6) . ?
C7A C8A 1.355(5) . ?
C7A H7A 0.95(4) . ?
C14 H14 0.9300 . ?
C14 C13 1.387(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.386(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.494(6) . ?
C13 H13 0.9300 . ?
C13 C12 1.368(6) . ?
C12 H12 0.9300 . ?
C12 C11 1.385(6) . ?
C10A H10A 0.9300 . ?
C10A C11A 1.370(6) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C11 H11 0.9300 . ?
C15A H15C 0.9700 . ?
C15A H15D 0.9700 . ?
C15A C16A 1.505(6) . ?
C14A H14A 0.9300 . ?
C14A C13A 1.386(7) . ?
C11A H11A 0.9300 . ?
C11A C12A 1.377(7) . ?
C12A H12A 0.9300 . ?
C12A C13A 1.374(7) . ?
C16A H16D 0.9600 . ?
C16A H16E 0.9600 . ?
C16A H16F 0.9600 . ?
C13A H13A 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
C1 O2 C15 116.9(3) . . ?
C1A O2A C15A 117.5(3) . . ?
C2 N1 H1 121(3) . . ?
C5 N1 C2 110.6(3) . . ?
C5 N1 H1 128(3) . . ?
C6 O3 H3 100(2) . . ?
C8 O4 H3 102(3) . . ?
C8A O4A H4A 109.5 . . ?
C2A N1A H1A 118(4) . . ?
C5A N1A C2A 110.4(3) . . ?
C5A N1A H1A 131(4) . . ?
N1 C2 C3 107.2(3) . . ?
N1 C2 C1 114.8(3) . . ?
C3 C2 C1 137.9(3) . . ?
C2 C3 C4 106.8(3) . . ?
C2 C3 C17 126.9(3) . . ?
C4 C3 C17 126.0(3) . . ?
C3 C4 C6 129.9(3) . . ?
C5 C4 C3 106.7(3) . . ?
C5 C4 C6 123.3(3) . . ?
O2 C1 C2 116.0(3) . . ?
O1 C1 O2 123.9(3) . . ?
O1 C1 C2 120.0(3) . . ?
N1A C2A C3A 107.0(3) . . ?
N1A C2A C1A 114.4(3) . . ?
C3A C2A C1A 138.7(4) . . ?
C3A C4A C6A 129.8(3) . . ?
C5A C4A C3A 106.2(3) . . ?
C5A C4A C6A 123.9(4) . . ?
C2A C3A C4A 107.4(3) . . ?
C2A C3A C17A 127.4(4) . . ?
C4A C3A C17A 125.2(3) . . ?
N1 C5 C4 108.7(3) . . ?
N1 C5 H5 119.1(19) . . ?
C4 C5 H5 132.0(19) . . ?
O3 C6 C4 118.4(4) . . ?
O3 C6 C7 120.8(3) . . ?
C7 C6 C4 120.7(3) . . ?
O3A C6A C4A 120.6(4) . . ?
O3A C6A C7A 119.9(4) . . ?
C7A C6A C4A 119.5(3) . . ?
O4 C8 C9 115.5(3) . . ?
O4 C8 C7 120.1(4) . . ?
C7 C8 C9 124.4(4) . . ?
C14 C9 C8 120.3(4) . . ?
C14 C9 C10 117.9(4) . . ?
C10 C9 C8 121.8(3) . . ?
N1A C5A C4A 109.0(4) . . ?
N1A C5A H5A 125(2) . . ?
C4A C5A H5A 126(2) . . ?
F2 C17 F1 105.1(4) . . ?
F2 C17 C3 113.6(3) . . ?
F1 C17 C3 111.1(3) . . ?
F3 C17 F2 106.5(3) . . ?
F3 C17 F1 106.8(3) . . ?
F3 C17 C3 113.2(3) . . ?
C6 C7 H7 119(3) . . ?
C8 C7 C6 121.8(4) . . ?
C8 C7 H7 119(3) . . ?
C10A C9A C8A 120.5(4) . . ?
C10A C9A C14A 118.0(4) . . ?
C14A C9A C8A 121.6(4) . . ?
C6A C7A H7A 117(3) . . ?
C8A C7A C6A 122.2(4) . . ?
C8A C7A H7A 121(3) . . ?
O2A C1A C2A 114.7(3) . . ?
O1A C1A O2A 123.6(4) . . ?
O1A C1A C2A 121.6(4) . . ?
O4A C8A C9A 113.1(3) . . ?
O4A C8A C7A 121.0(4) . . ?
C7A C8A C9A 125.9(4) . . ?
C9 C14 H14 119.4 . . ?
C13 C14 C9 121.2(4) . . ?
C13 C14 H14 119.4 . . ?
F2A C17A F3A 105.6(4) . . ?
F2A C17A F1A 104.5(4) . . ?
F2A C17A C3A 113.0(4) . . ?
F3A C17A C3A 110.5(4) . . ?
F1A C17A F3A 109.0(4) . . ?
F1A C17A C3A 113.8(3) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.8(4) . . ?
C11 C10 H10 119.6 . . ?
O2 C15 H15A 109.7 . . ?
O2 C15 H15B 109.7 . . ?
O2 C15 C16 109.8(3) . . ?
H15A C15 H15B 108.2 . . ?
C16 C15 H15A 109.7 . . ?
C16 C15 H15B 109.7 . . ?
C14 C13 H13 119.9 . . ?
C12 C13 C14 120.2(4) . . ?
C12 C13 H13 119.9 . . ?
C13 C12 H12 120.1 . . ?
C13 C12 C11 119.8(4) . . ?
C11 C12 H12 120.1 . . ?
C9A C10A H10A 119.2 . . ?
C11A C10A C9A 121.6(5) . . ?
C11A C10A H10A 119.2 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.0(4) . . ?
C12 C11 H11 120.0 . . ?
O2A C15A H15C 110.2 . . ?
O2A C15A H15D 110.2 . . ?
O2A C15A C16A 107.3(4) . . ?
H15C C15A H15D 108.5 . . ?
C16A C15A H15C 110.2 . . ?
C16A C15A H15D 110.2 . . ?
C9A C14A H14A 120.0 . . ?
C13A C14A C9A 120.0(5) . . ?
C13A C14A H14A 120.0 . . ?
C10A C11A H11A 120.0 . . ?
C10A C11A C12A 119.9(5) . . ?
C12A C11A H11A 120.0 . . ?
C11A C12A H12A 120.1 . . ?
C13A C12A C11A 119.8(5) . . ?
C13A C12A H12A 120.1 . . ?
C15A C16A H16D 109.5 . . ?
C15A C16A H16E 109.5 . . ?
C15A C16A H16F 109.5 . . ?
H16D C16A H16E 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 109.5 . . ?
C14A C13A H13A 119.6 . . ?
C12A C13A C14A 120.8(5) . . ?
C12A C13A H13A 119.6 . . ?

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
O3A C6A C7A C8A 1.3(7) . . . . ?
N1 C2 C3 C4 1.1(4) . . . . ?
N1 C2 C3 C17 -173.1(3) . . . . ?
N1 C2 C1 O2 -159.8(3) . . . . ?
N1 C2 C1 O1 18.1(5) . . . . ?
O3 C6 C7 C8 0.1(7) . . . . ?
O4 C8 C9 C14 3.7(6) . . . . ?
O4 C8 C9 C10 -176.5(4) . . . . ?
O4 C8 C7 C6 3.1(7) . . . . ?
N1A C2A C3A C4A 0.1(4) . . . . ?
N1A C2A C3A C17A 178.3(4) . . . . ?
N1A C2A C1A O2A 168.6(3) . . . . ?
N1A C2A C1A O1A -11.3(6) . . . . ?
C2 N1 C5 C4 -0.1(4) . . . . ?
C2 C3 C4 C5 -1.1(4) . . . . ?
C2 C3 C4 C6 175.6(4) . . . . ?
C2 C3 C17 F2 11.1(6) . . . . ?
C2 C3 C17 F1 129.3(4) . . . . ?
C2 C3 C17 F3 -110.6(4) . . . . ?
C3 C2 C1 O2 19.5(7) . . . . ?
C3 C2 C1 O1 -162.6(4) . . . . ?
C3 C4 C5 N1 0.7(4) . . . . ?
C3 C4 C6 O3 -12.3(6) . . . . ?
C3 C4 C6 C7 169.9(4) . . . . ?
C4 C3 C17 F2 -162.1(3) . . . . ?
C4 C3 C17 F1 -43.8(5) . . . . ?
C4 C3 C17 F3 76.3(5) . . . . ?
C4 C6 C7 C8 177.8(4) . . . . ?
C1 O2 C15 C16 -93.7(4) . . . . ?
C1 C2 C3 C4 -178.2(4) . . . . ?
C1 C2 C3 C17 7.6(7) . . . . ?
C2A N1A C5A C4A -0.4(5) . . . . ?
C2A C3A C17A F2A -133.8(4) . . . . ?
C2A C3A C17A F3A 108.1(5) . . . . ?
C2A C3A C17A F1A -14.8(7) . . . . ?
C4A C3A C17A F2A 44.1(6) . . . . ?
C4A C3A C17A F3A -73.9(5) . . . . ?
C4A C3A C17A F1A 163.1(4) . . . . ?
C4A C6A C7A C8A -177.7(4) . . . . ?
C3A C2A C1A O2A -11.0(7) . . . . ?
C3A C2A C1A O1A 169.1(5) . . . . ?
C3A C4A C6A O3A 9.6(7) . . . . ?
C3A C4A C6A C7A -171.4(4) . . . . ?
C3A C4A C5A N1A 0.4(5) . . . . ?
C5 N1 C2 C3 -0.7(4) . . . . ?
C5 N1 C2 C1 178.8(3) . . . . ?
C5 C4 C6 O3 163.9(4) . . . . ?
C5 C4 C6 C7 -13.8(6) . . . . ?
C6 C4 C5 N1 -176.2(3) . . . . ?
C6A C4A C3A C2A -176.7(4) . . . . ?
C6A C4A C3A C17A 5.0(7) . . . . ?
C6A C4A C5A N1A 177.1(4) . . . . ?
C6A C7A C8A O4A 0.1(7) . . . . ?
C6A C7A C8A C9A 178.9(4) . . . . ?
C8 C9 C14 C13 178.2(4) . . . . ?
C8 C9 C10 C11 -179.5(4) . . . . ?
C9 C8 C7 C6 -176.9(4) . . . . ?
C9 C14 C13 C12 1.2(7) . . . . ?
C9 C10 C11 C12 1.6(7) . . . . ?
C5A N1A C2A C3A 0.2(5) . . . . ?
C5A N1A C2A C1A -179.5(4) . . . . ?
C5A C4A C3A C2A -0.3(4) . . . . ?
C5A C4A C3A C17A -178.6(4) . . . . ?
C5A C4A C6A O3A -166.3(4) . . . . ?
C5A C4A C6A C7A 12.7(6) . . . . ?
C17 C3 C4 C5 173.2(4) . . . . ?
C17 C3 C4 C6 -10.1(6) . . . . ?
C7 C8 C9 C14 -176.2(4) . . . . ?
C7 C8 C9 C10 3.5(6) . . . . ?
C9A C10A C11A C12A 0.8(8) . . . . ?
C9A C14A C13A C12A -0.8(8) . . . . ?
C1A O2A C15A C16A -169.4(4) . . . . ?
C1A C2A C3A C4A 179.7(5) . . . . ?
C1A C2A C3A C17A -2.1(8) . . . . ?
C8A C9A C10A C11A 179.2(4) . . . . ?
C8A C9A C14A C13A -179.2(5) . . . . ?
C14 C9 C10 C11 0.2(6) . . . . ?
C14 C13 C12 C11 0.7(7) . . . . ?
C10 C9 C14 C13 -1.6(6) . . . . ?
C15 O2 C1 O1 2.0(6) . . . . ?
C15 O2 C1 C2 179.8(3) . . . . ?
C13 C12 C11 C10 -2.1(7) . . . . ?
C10A C9A C8A O4A -14.6(6) . . . . ?
C10A C9A C8A C7A 166.5(4) . . . . ?
C10A C9A C14A C13A -0.1(7) . . . . ?
C10A C11A C12A C13A -1.7(8) . . . . ?
C15A O2A C1A O1A -0.7(6) . . . . ?
C15A O2A C1A C2A 179.5(3) . . . . ?
C14A C9A C8A O4A 164.4(4) . . . . ?
C14A C9A C8A C7A -14.5(7) . . . . ?
C14A C9A C10A C11A 0.1(7) . . . . ?
C11A C12A C13A C14A 1.8(9) . . . . ?


_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
;
####################################################################### 
# 
# 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_exp_1224
_database_code_depnum_ccdc_archive 'CCDC 2297093'
loop_
_audit_author_name
_audit_author_address
'Alexey Barkov'
;Ural Federal University
Russia
;
_audit_update_record             
;
2023-09-24 deposited with the CCDC.	2025-10-29 downloaded from the CCDC.
;
_audit_creation_date             2023-09-04
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H14 F3 N O2'
_chemical_formula_sum            'C20 H14 F3 N O2'
_chemical_formula_weight         357.32
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   5.2062(6)
_cell_length_b                   13.1121(8)
_cell_length_c                   24.064(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1642.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1299
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.4250
_cell_measurement_theta_min      2.9660
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.05399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.98a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0974
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4701
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.77
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9555
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9762
_diffrn_measured_fraction_theta_max 0.8488
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -84.00 -46.00   1.00   50.00    --  -18.90-178.00-180.00   38
  2  ω    -39.00  46.00   1.00   50.00    --   21.25 -77.00  30.00   85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0884603000
_diffrn_orient_matrix_UB_12      -0.0401964000
_diffrn_orient_matrix_UB_13      0.0044276000
_diffrn_orient_matrix_UB_21      0.0583907000
_diffrn_orient_matrix_UB_22      0.0284647000
_diffrn_orient_matrix_UB_23      0.0217759000
_diffrn_orient_matrix_UB_31      -0.0847605000
_diffrn_orient_matrix_UB_32      -0.0226618000
_diffrn_orient_matrix_UB_33      0.0194521000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1681
_reflns_number_total             3431
_reflns_odcompleteness_completeness 97.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(17)
_refine_ls_extinction_coef       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3431
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1292
_refine_ls_R_factor_gt           0.0639
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0623P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1895
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.5698(8) -0.8458(2) -0.22216(14) 0.0724(11) Uani 1 1 d . . .
F3 F -1.0308(8) -0.8406(2) -0.37307(13) 0.1052(13) Uani 1 1 d . . .
F1 F -0.9941(8) -0.88870(19) -0.28903(13) 0.0952(12) Uani 1 1 d . . .
O2 O -0.2249(8) -0.8571(2) -0.15215(16) 0.0747(11) Uani 1 1 d . . .
F2 F -0.6648(7) -0.8824(2) -0.34085(16) 0.1052(13) Uani 1 1 d . . .
N1 N -0.8746(9) -0.5585(2) -0.30481(16) 0.0595(11) Uani 1 1 d . . .
C2 C -0.9471(9) -0.6407(3) -0.33614(19) 0.0528(11) Uani 1 1 d . . .
C6 C -0.5275(10) -0.7486(3) -0.22606(17) 0.0539(11) Uani 1 1 d . . .
C8 C -0.1882(10) -0.7592(3) -0.15686(18) 0.0532(11) Uani 1 1 d . . .
C4 C -0.6868(10) -0.6920(3) -0.26452(18) 0.0516(12) Uani 1 1 d . . .
C5 C -0.7190(10) -0.5871(3) -0.26241(18) 0.0559(12) Uani 1 1 d . . .
H5 H -0.6461 -0.5436 -0.2363 0.067 Uiso 1 1 calc R . .
C7 C -0.3368(9) -0.7031(3) -0.19405(17) 0.0530(12) Uani 1 1 d . . .
H7 H -0.3077 -0.6334 -0.1976 0.064 Uiso 1 1 calc R . .
C1 C -0.8794(12) -0.8328(3) -0.3278(2) 0.0671(14) Uani 1 1 d . . .
C3 C -0.8378(9) -0.7261(3) -0.31148(17) 0.0506(11) Uani 1 1 d . . .
C9 C 0.0169(10) -0.7150(3) -0.12116(17) 0.0529(11) Uani 1 1 d . . .
C15 C -1.0907(9) -0.6228(3) -0.38803(19) 0.0560(12) Uani 1 1 d . . .
C12 C 0.4020(11) -0.6382(4) -0.0536(2) 0.0689(14) Uani 1 1 d . . .
H12 H 0.5299 -0.6119 -0.0307 0.083 Uiso 1 1 calc R . .
C10 C 0.0689(10) -0.6112(3) -0.12023(19) 0.0616(13) Uani 1 1 d . . .
H10 H -0.0269 -0.5668 -0.1421 0.074 Uiso 1 1 calc R . .
C14 C 0.1606(10) -0.7782(3) -0.08747(18) 0.0606(13) Uani 1 1 d . . .
H14 H 0.1269 -0.8478 -0.0874 0.073 Uiso 1 1 calc R . .
C11 C 0.2640(11) -0.5738(3) -0.0867(2) 0.0683(15) Uani 1 1 d . . .
H11 H 0.3011 -0.5044 -0.0868 0.082 Uiso 1 1 calc R . .
C16 C -1.0013(11) -0.6591(3) -0.43903(19) 0.0663(13) Uani 1 1 d . . .
H16 H -0.8561 -0.7004 -0.4402 0.080 Uiso 1 1 calc R . .
C20 C -1.3047(11) -0.5594(3) -0.3873(2) 0.0700(14) Uani 1 1 d . . .
H20 H -1.3644 -0.5333 -0.3538 0.084 Uiso 1 1 calc R . .
C13 C 0.3554(11) -0.7400(4) -0.0535(2) 0.0706(15) Uani 1 1 d . . .
H13 H 0.4515 -0.7836 -0.0312 0.085 Uiso 1 1 calc R . .
C17 C -1.1269(13) -0.6344(4) -0.4880(2) 0.0828(18) Uani 1 1 d . . .
H17 H -1.0667 -0.6589 -0.5218 0.099 Uiso 1 1 calc R . .
C18 C -1.3431(14) -0.5726(4) -0.4861(3) 0.093(2) Uani 1 1 d . . .
H18 H -1.4301 -0.5567 -0.5187 0.111 Uiso 1 1 calc R . .
C19 C -1.4288(13) -0.5351(4) -0.4362(3) 0.089(2) Uani 1 1 d . . .
H19 H -1.5721 -0.4928 -0.4353 0.107 Uiso 1 1 calc R . .
H1A H -0.924(10) -0.486(4) -0.3152(18) 0.086(17) Uiso 1 1 d . . .
H1 H -0.342(17) -0.862(6) -0.190(3) 0.20(4) 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
O1 C6 1.296(5) . ?
O1 H1 1.43(9) . ?
F3 C1 1.349(6) . ?
F1 C1 1.328(6) . ?
O2 C8 1.302(5) . ?
O2 H1 1.10(8) . ?
F2 C1 1.331(6) . ?
N1 C2 1.369(5) . ?
N1 C5 1.356(6) . ?
N1 H1A 1.01(5) . ?
C2 C3 1.389(5) . ?
C2 C15 1.474(6) . ?
C6 C4 1.448(6) . ?
C6 C7 1.391(6) . ?
C8 C7 1.393(6) . ?
C8 C9 1.488(6) . ?
C4 C5 1.387(5) . ?
C4 C3 1.448(6) . ?
C5 H5 0.9300 . ?
C7 H7 0.9300 . ?
C1 C3 1.468(6) . ?
C9 C10 1.387(5) . ?
C9 C14 1.380(6) . ?
C15 C16 1.396(6) . ?
C15 C20 1.390(7) . ?
C12 H12 0.9300 . ?
C12 C11 1.366(6) . ?
C12 C13 1.357(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.387(6) . ?
C14 H14 0.9300 . ?
C14 C13 1.396(7) . ?
C11 H11 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.386(7) . ?
C20 H20 0.9300 . ?
C20 C19 1.378(7) . ?
C13 H13 0.9300 . ?
C17 H17 0.9300 . ?
C17 C18 1.387(8) . ?
C18 H18 0.9300 . ?
C18 C19 1.372(8) . ?
C19 H19 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O1 H1 92(3) . . ?
C8 O2 H1 94(4) . . ?
C2 N1 H1A 122(3) . . ?
C5 N1 C2 111.2(3) . . ?
C5 N1 H1A 127(3) . . ?
N1 C2 C3 106.7(4) . . ?
N1 C2 C15 118.7(4) . . ?
C3 C2 C15 134.2(4) . . ?
O1 C6 C4 116.9(4) . . ?
O1 C6 C7 120.2(4) . . ?
C7 C6 C4 122.9(4) . . ?
O2 C8 C7 119.7(4) . . ?
O2 C8 C9 116.1(4) . . ?
C7 C8 C9 124.3(3) . . ?
C5 C4 C6 123.7(4) . . ?
C5 C4 C3 105.7(4) . . ?
C3 C4 C6 130.6(3) . . ?
N1 C5 C4 108.6(4) . . ?
N1 C5 H5 125.7 . . ?
C4 C5 H5 125.7 . . ?
C6 C7 C8 121.7(4) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
F3 C1 C3 112.0(4) . . ?
F1 C1 F3 105.2(4) . . ?
F1 C1 F2 105.9(4) . . ?
F1 C1 C3 113.9(4) . . ?
F2 C1 F3 105.2(5) . . ?
F2 C1 C3 113.9(5) . . ?
C2 C3 C4 107.8(3) . . ?
C2 C3 C1 126.4(4) . . ?
C4 C3 C1 125.7(4) . . ?
C10 C9 C8 122.1(4) . . ?
C14 C9 C8 119.6(4) . . ?
C14 C9 C10 118.3(4) . . ?
C16 C15 C2 121.4(4) . . ?
C20 C15 C2 119.4(5) . . ?
C20 C15 C16 118.8(5) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C13 C12 C11 121.0(5) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 119.9(5) . . ?
C11 C10 H10 120.0 . . ?
C9 C14 H14 119.2 . . ?
C9 C14 C13 121.5(4) . . ?
C13 C14 H14 119.2 . . ?
C12 C11 C10 120.4(4) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.7(5) . . ?
C17 C16 H16 119.7 . . ?
C15 C20 H20 119.9 . . ?
C19 C20 C15 120.3(5) . . ?
C19 C20 H20 119.9 . . ?
C12 C13 C14 118.8(5) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?
C16 C17 H17 120.3 . . ?
C16 C17 C18 119.4(6) . . ?
C18 C17 H17 120.3 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.2(6) . . ?
C19 C18 H18 119.9 . . ?
C20 C19 H19 119.7 . . ?
C18 C19 C20 120.7(6) . . ?
C18 C19 H19 119.7 . . ?

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 C6 C4 C5 160.8(5) . . . . ?
O1 C6 C4 C3 -20.2(8) . . . . ?
O1 C6 C7 C8 -0.6(7) . . . . ?
F3 C1 C3 C2 3.4(8) . . . . ?
F3 C1 C3 C4 179.4(4) . . . . ?
F1 C1 C3 C2 -115.8(6) . . . . ?
F1 C1 C3 C4 60.2(7) . . . . ?
O2 C8 C7 C6 0.9(7) . . . . ?
O2 C8 C9 C10 -177.2(5) . . . . ?
O2 C8 C9 C14 2.4(6) . . . . ?
F2 C1 C3 C2 122.6(6) . . . . ?
F2 C1 C3 C4 -61.3(7) . . . . ?
N1 C2 C3 C4 -2.0(5) . . . . ?
N1 C2 C3 C1 174.6(5) . . . . ?
N1 C2 C15 C16 123.3(5) . . . . ?
N1 C2 C15 C20 -49.8(6) . . . . ?
C2 N1 C5 C4 -0.7(6) . . . . ?
C2 C15 C16 C17 -174.5(4) . . . . ?
C2 C15 C20 C19 174.7(4) . . . . ?
C6 C4 C5 N1 178.7(4) . . . . ?
C6 C4 C3 C2 -177.6(5) . . . . ?
C6 C4 C3 C1 5.8(9) . . . . ?
C8 C9 C10 C11 -179.3(4) . . . . ?
C8 C9 C14 C13 179.8(4) . . . . ?
C4 C6 C7 C8 179.2(4) . . . . ?
C5 N1 C2 C3 1.7(5) . . . . ?
C5 N1 C2 C15 -172.6(4) . . . . ?
C5 C4 C3 C2 1.6(6) . . . . ?
C5 C4 C3 C1 -175.1(5) . . . . ?
C7 C6 C4 C5 -19.0(8) . . . . ?
C7 C6 C4 C3 160.0(5) . . . . ?
C7 C8 C9 C10 3.2(7) . . . . ?
C7 C8 C9 C14 -177.1(4) . . . . ?
C3 C2 C15 C16 -49.2(7) . . . . ?
C3 C2 C15 C20 137.8(5) . . . . ?
C3 C4 C5 N1 -0.6(6) . . . . ?
C9 C8 C7 C6 -179.5(4) . . . . ?
C9 C10 C11 C12 -1.4(8) . . . . ?
C9 C14 C13 C12 0.4(7) . . . . ?
C15 C2 C3 C4 171.1(5) . . . . ?
C15 C2 C3 C1 -12.3(9) . . . . ?
C15 C16 C17 C18 0.1(8) . . . . ?
C15 C20 C19 C18 -0.2(8) . . . . ?
C10 C9 C14 C13 -0.5(7) . . . . ?
C14 C9 C10 C11 1.0(7) . . . . ?
C11 C12 C13 C14 -0.8(8) . . . . ?
C16 C15 C20 C19 1.4(7) . . . . ?
C16 C17 C18 C19 1.1(8) . . . . ?
C20 C15 C16 C17 -1.4(7) . . . . ?
C13 C12 C11 C10 1.3(8) . . . . ?
C17 C18 C19 C20 -1.1(9) . . . . ?

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 10.138
_oxdiff_exptl_absorpt_empirical_full_min 0.483
####################################################################### 
# 
# 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_exp_1812
_database_code_depnum_ccdc_archive 'CCDC 2491605'
loop_
_audit_author_name
_audit_author_address
'Alexey Barkov'
;Ural Federal University
Russia
;
_audit_update_record             
;
2025-09-26 deposited with the CCDC.	2025-10-29 downloaded from the CCDC.
;
_audit_creation_date             2025-09-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H13 F3 N2 O3'
_chemical_formula_sum            'C17 H13 F3 N2 O3'
_chemical_formula_weight         350.29
_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 0.0033 0.0016 '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 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   13.0298(7)
_cell_length_b                   7.5259(7)
_cell_length_c                   31.6005(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3098.8(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1425
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      24.7080
_cell_measurement_theta_min      3.0080
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.941
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.98a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1440
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0997
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.844
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            8639
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.176
_diffrn_reflns_theta_min         3.015
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 15.9555
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.844
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -39.00  -6.00   1.00   60.00    --  -19.06 -77.00-180.00   33
  2  ω    -32.00   0.00   1.00   60.00    --  -19.06 -77.00  60.00   32
  3  ω    -14.00  46.00   1.00   60.00    --   21.56 -19.00  60.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur 3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1771
_reflns_number_total             4226
_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 1.171.41.98a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_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         0.204
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1781
_refine_ls_R_factor_gt           0.0631
_refine_ls_restrained_S_all      0.976
_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)+(0.0387P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1361
_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.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C7(H7), C10(H10), C9(H9), C8(H8)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_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
F2 F 0.47129(10) 0.2425(2) 0.78839(5) 0.0535(5) Uani 1 1 d . . . . .
O1 O 0.39917(11) 0.4024(2) 0.71549(5) 0.0408(5) Uani 1 1 d . . . . .
F1 F 0.47954(11) 0.5159(3) 0.80430(6) 0.0744(6) Uani 1 1 d . . . . .
F3 F 0.45470(10) 0.3209(3) 0.85221(5) 0.0890(8) Uani 1 1 d . . . . .
O2 O 0.14970(13) 0.4689(3) 0.89713(5) 0.0634(7) Uani 1 1 d . . . . .
N1 N 0.14878(15) 0.3980(3) 0.81660(6) 0.0411(6) Uani 1 1 d . . . . .
N2 N 0.42180(15) 0.3684(3) 0.67247(6) 0.0400(6) Uani 1 1 d . . . . .
C5 C 0.30656(16) 0.3305(4) 0.72462(7) 0.0336(6) Uani 1 1 d . . . . .
O3 O 0.31922(14) 0.4903(4) 0.90221(6) 0.0840(9) Uani 1 1 d . . . . .
C16 C 0.26611(16) 0.3556(4) 0.76703(7) 0.0333(6) Uani 1 1 d . . . . .
C3 C 0.34277(17) 0.2791(4) 0.65778(7) 0.0351(7) Uani 1 1 d . . . . .
C4 C 0.2676(2) 0.2545(4) 0.68951(8) 0.0382(7) Uani 1 1 d . . . . .
C15 C 0.31674(16) 0.3811(4) 0.80646(7) 0.0328(6) Uani 1 1 d . . . . .
C6 C 0.34317(18) 0.2160(4) 0.61356(7) 0.0384(7) Uani 1 1 d . . . . .
C17 C 0.16253(18) 0.3679(4) 0.77514(8) 0.0409(7) Uani 1 1 d . . . . .
C2 C 0.24142(17) 0.4096(4) 0.83676(7) 0.0359(7) Uani 1 1 d . . . . .
C14 C 0.2445(2) 0.4591(4) 0.88205(8) 0.0445(8) Uani 1 1 d . . . . .
C1 C 0.42924(19) 0.3670(5) 0.81332(8) 0.0451(8) Uani 1 1 d . . . . .
C11 C 0.43315(19) 0.1668(4) 0.59390(8) 0.0520(8) Uani 1 1 d . . . . .
H11 H 0.494700 0.172592 0.608737 0.062 Uiso 1 1 calc R U . . .
C7 C 0.25193(19) 0.2032(5) 0.59117(8) 0.0590(10) Uani 1 1 d . . . . .
H7 H 0.190218 0.233178 0.604127 0.071 Uiso 1 1 calc R U . . .
C10 C 0.4330(2) 0.1090(5) 0.55246(9) 0.0618(10) Uani 1 1 d . . . . .
H10 H 0.494381 0.076846 0.539538 0.074 Uiso 1 1 calc R U . . .
C9 C 0.3427(2) 0.0989(4) 0.53023(9) 0.0662(10) Uani 1 1 d . . . . .
H9 H 0.342732 0.060322 0.502269 0.079 Uiso 1 1 calc R U . . .
C8 C 0.2527(2) 0.1459(5) 0.54950(9) 0.0726(12) Uani 1 1 d . . . . .
H8 H 0.191423 0.139219 0.534495 0.087 Uiso 1 1 calc R U . . .
C13 C 0.0354(2) 0.6065(5) 0.94541(9) 0.0762(11) Uani 1 1 d . . . . .
H13A H 0.032433 0.711619 0.928236 0.114 Uiso 1 1 calc R U . . .
H13B H 0.023944 0.637699 0.974484 0.114 Uiso 1 1 calc R U . . .
H13C H -0.016548 0.524430 0.936345 0.114 Uiso 1 1 calc R U . . .
C12 C 0.1373(2) 0.5232(6) 0.94104(9) 0.0786(13) Uani 1 1 d . . . . .
H12A H 0.190608 0.607183 0.948772 0.094 Uiso 1 1 calc R U . . .
H12B H 0.142507 0.420762 0.959539 0.094 Uiso 1 1 calc R U . . .
H17 H 0.1043(16) 0.356(3) 0.7566(7) 0.045(7) Uiso 1 1 d . . . . .
H1 H 0.085(2) 0.413(4) 0.8274(8) 0.069(9) Uiso 1 1 d . . . . .
H4 H 0.2039(18) 0.199(4) 0.6861(7) 0.052(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F2 C1 1.341(3) . ?
O1 N2 1.414(2) . ?
O1 C5 1.353(3) . ?
F1 C1 1.329(3) . ?
F3 C1 1.319(3) . ?
O2 C14 1.327(3) . ?
O2 C12 1.455(3) . ?
N1 C17 1.342(3) . ?
N1 C2 1.368(3) . ?
N1 H1 0.91(3) . ?
N2 C3 1.314(3) . ?
C5 C16 1.453(3) . ?
C5 C4 1.347(3) . ?
O3 C14 1.187(3) . ?
C16 C15 1.423(3) . ?
C16 C17 1.377(3) . ?
C3 C4 1.414(3) . ?
C3 C6 1.476(3) . ?
C4 H4 0.93(2) . ?
C15 C2 1.388(3) . ?
C15 C1 1.486(3) . ?
C6 C11 1.377(3) . ?
C6 C7 1.387(3) . ?
C17 H17 0.96(2) . ?
C2 C14 1.479(3) . ?
C11 H11 0.9300 . ?
C11 C10 1.380(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.386(4) . ?
C10 H10 0.9300 . ?
C10 C9 1.372(4) . ?
C9 H9 0.9300 . ?
C9 C8 1.368(4) . ?
C8 H8 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C13 C12 1.475(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?

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
C5 O1 N2 108.57(17) . . ?
C14 O2 C12 117.5(2) . . ?
C17 N1 C2 110.4(2) . . ?
C17 N1 H1 120.7(17) . . ?
C2 N1 H1 128.8(18) . . ?
C3 N2 O1 105.59(18) . . ?
O1 C5 C16 117.9(2) . . ?
C4 C5 O1 109.3(2) . . ?
C4 C5 C16 132.7(2) . . ?
C15 C16 C5 131.1(2) . . ?
C17 C16 C5 122.4(2) . . ?
C17 C16 C15 106.4(2) . . ?
N2 C3 C4 111.0(2) . . ?
N2 C3 C6 119.8(2) . . ?
C4 C3 C6 129.2(2) . . ?
C5 C4 C3 105.5(2) . . ?
C5 C4 H4 128.1(15) . . ?
C3 C4 H4 126.4(15) . . ?
C16 C15 C1 125.1(2) . . ?
C2 C15 C16 107.29(19) . . ?
C2 C15 C1 127.5(2) . . ?
C11 C6 C3 121.1(2) . . ?
C11 C6 C7 118.7(2) . . ?
C7 C6 C3 120.2(2) . . ?
N1 C17 C16 108.9(2) . . ?
N1 C17 H17 120.4(13) . . ?
C16 C17 H17 130.7(13) . . ?
N1 C2 C15 107.0(2) . . ?
N1 C2 C14 119.4(2) . . ?
C15 C2 C14 133.4(2) . . ?
O2 C14 C2 109.6(2) . . ?
O3 C14 O2 124.0(2) . . ?
O3 C14 C2 126.3(2) . . ?
F2 C1 C15 111.6(2) . . ?
F1 C1 F2 105.2(2) . . ?
F1 C1 C15 113.2(2) . . ?
F3 C1 F2 105.1(2) . . ?
F3 C1 F1 107.3(2) . . ?
F3 C1 C15 113.8(2) . . ?
C6 C11 H11 119.6 . . ?
C6 C11 C10 120.8(3) . . ?
C10 C11 H11 119.6 . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 120.0(2) . . ?
C8 C7 H7 120.0 . . ?
C11 C10 H10 119.9 . . ?
C9 C10 C11 120.3(3) . . ?
C9 C10 H10 119.9 . . ?
C10 C9 H9 120.2 . . ?
C8 C9 C10 119.5(3) . . ?
C8 C9 H9 120.2 . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.6(3) . . ?
C9 C8 H8 119.7 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
O2 C12 C13 107.9(2) . . ?
O2 C12 H12A 110.1 . . ?
O2 C12 H12B 110.1 . . ?
C13 C12 H12A 110.1 . . ?
C13 C12 H12B 110.1 . . ?
H12A C12 H12B 108.4 . . ?

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
O1 N2 C3 C4 0.7(3) . . . . ?
O1 N2 C3 C6 -177.8(2) . . . . ?
O1 C5 C16 C15 -27.9(4) . . . . ?
O1 C5 C16 C17 148.5(3) . . . . ?
O1 C5 C4 C3 1.4(3) . . . . ?
N1 C2 C14 O2 5.8(4) . . . . ?
N1 C2 C14 O3 -172.3(3) . . . . ?
N2 O1 C5 C16 -177.7(2) . . . . ?
N2 O1 C5 C4 -1.0(3) . . . . ?
N2 C3 C4 C5 -1.4(3) . . . . ?
N2 C3 C6 C11 32.6(4) . . . . ?
N2 C3 C6 C7 -148.2(3) . . . . ?
C5 O1 N2 C3 0.2(3) . . . . ?
C5 C16 C15 C2 176.2(3) . . . . ?
C5 C16 C15 C1 -7.5(5) . . . . ?
C5 C16 C17 N1 -177.5(3) . . . . ?
C16 C5 C4 C3 177.4(3) . . . . ?
C16 C15 C2 N1 1.2(3) . . . . ?
C16 C15 C2 C14 -173.7(3) . . . . ?
C16 C15 C1 F2 -34.0(4) . . . . ?
C16 C15 C1 F1 84.5(3) . . . . ?
C16 C15 C1 F3 -152.7(3) . . . . ?
C3 C6 C11 C10 -179.6(3) . . . . ?
C3 C6 C7 C8 179.3(3) . . . . ?
C4 C5 C16 C15 156.3(3) . . . . ?
C4 C5 C16 C17 -27.3(5) . . . . ?
C4 C3 C6 C11 -145.6(3) . . . . ?
C4 C3 C6 C7 33.5(5) . . . . ?
C15 C16 C17 N1 -0.3(3) . . . . ?
C15 C2 C14 O2 -179.7(3) . . . . ?
C15 C2 C14 O3 2.2(6) . . . . ?
C6 C3 C4 C5 177.0(3) . . . . ?
C6 C11 C10 C9 -0.4(5) . . . . ?
C6 C7 C8 C9 1.0(6) . . . . ?
C17 N1 C2 C15 -1.5(3) . . . . ?
C17 N1 C2 C14 174.4(3) . . . . ?
C17 C16 C15 C2 -0.6(3) . . . . ?
C17 C16 C15 C1 175.7(3) . . . . ?
C2 N1 C17 C16 1.1(4) . . . . ?
C2 C15 C1 F2 141.6(3) . . . . ?
C2 C15 C1 F1 -100.0(3) . . . . ?
C2 C15 C1 F3 22.9(5) . . . . ?
C14 O2 C12 C13 153.3(3) . . . . ?
C1 C15 C2 N1 -175.0(3) . . . . ?
C1 C15 C2 C14 10.1(5) . . . . ?
C11 C6 C7 C8 -1.5(5) . . . . ?
C11 C10 C9 C8 -0.2(5) . . . . ?
C7 C6 C11 C10 1.2(5) . . . . ?
C10 C9 C8 C7 -0.1(6) . . . . ?
C12 O2 C14 O3 0.6(5) . . . . ?
C12 O2 C14 C2 -177.6(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;

