# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_jft-01-537
_database_code_depnum_ccdc_archive 'CCDC 2141776'
loop_
_audit_author_name
_audit_author_address
'Farzaneh Fadaei Tirani'
;EPFL
Switzerland
;
_audit_update_record             
;
2022-01-13 deposited with the CCDC.	2022-02-09 downloaded from the CCDC.
;
_audit_creation_date             2020-07-29
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_shelx_SHELXL_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H21 F4 N3'
_chemical_formula_sum            'C18 H21 F4 N3'
_chemical_formula_weight         355.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H21 F4 N3'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.21581(8)
_cell_length_b                   14.44752(14)
_cell_length_c                   13.23644(14)
_cell_angle_alpha                90
_cell_angle_beta                 91.4811(9)
_cell_angle_gamma                90
_cell_volume                     1761.79(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11336
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      75.5750
_cell_measurement_theta_min      3.0440
_shelx_estimated_absorpt_T_max   0.906
_shelx_estimated_absorpt_T_min   0.729
_exptl_absorpt_coefficient_mu    0.941
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.399
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.41.76a (Rigaku Oxford Diffraction, 2020)
 Numerical absorption correction based on Gaussian integration over
 a multifaceted crystal model.
 Empirical absorption correction using spherical harmonics
 as implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             744
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 2 1 0.0375
0 -2 -1 0.0691
0 1 -1 0.1422
1 -2 1 0.1089
0 -1 1 0.1302
2 0 1 0.1359
-2 0 -1 0.1022
1 -1 0 0.1182
-1 1 2 0.1184
-1 -1 1 0.1557
1 1 -1 0.2044
-1 2 0 0.1028
1 1 0 0.1503

_exptl_crystal_size_max          0.358
_exptl_crystal_size_mid          0.247
_exptl_crystal_size_min          0.107
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0006 1.9995 1.0003 -0.2059 -0.0126 -0.1278
0.0006 -1.9995 -1.0003 0.2059 0.0126 0.1278
-0.0001 0.9997 -0.9982 -0.0156 0.1447 -0.0607
0.9998 -1.9997 0.9975 0.0007 -0.1453 0.2585
0.0001 -0.9997 0.9982 0.0156 -0.1447 0.0607
1.9988 -0.0005 0.9990 -0.2357 -0.0136 0.2677
-1.9988 0.0005 -0.9990 0.2357 0.0136 -0.2677
0.9997 -1.0000 -0.0007 -0.0149 -0.0005 0.1977
-0.9999 1.0001 1.9985 -0.1016 -0.2009 -0.2020
-0.9994 -0.9994 0.9982 0.1044 -0.1883 -0.0742
0.9994 0.9994 -0.9982 -0.1044 0.1883 0.0742
-0.9999 1.9997 0.0014 -0.0590 0.0446 -0.2606
0.9992 0.9995 0.0007 -0.1626 0.0876 0.0720

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18746
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.037
_diffrn_reflns_theta_min         4.531
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -72.00  33.00   1.00    1.00    --  -40.91  72.00-145.00  105
  2  ω    -98.00 -19.00   1.00    1.00    --  -40.91 -72.00  84.00   79
  3  ω     38.00  63.00   1.00    1.00    --   40.91  72.00-145.00   25
  4  ω     -5.00  20.00   1.00    1.00    --   40.91 -72.00  84.00   25
  5  ω     51.00  92.00   1.00    4.00    --  112.00 -72.00  84.00   41
  6  ω    131.00 158.00   1.00    4.00    --  112.00  72.00-145.00   27
  7  ω      7.00  32.00   1.00    1.00    --  -40.91  57.00   0.00   25
  8  ω     20.00 113.00   1.00    1.00    --   40.91  38.00 -30.00   93
  9  ω     42.00  97.00   1.00    1.00    --   40.91-125.00   0.00   55
 10  ω    -31.00  63.00   1.00    1.00    --   40.91 -38.00 -30.00   94
 11  ω     43.00  89.00   1.00    4.00    --  112.00-111.00  60.00   46
 12  ω     98.00 178.00   1.00    4.00    --  112.00  45.00 -30.00   80
 13  ω    103.00 178.00   1.00    4.00    --  112.00  77.00-180.00   75
 14  ω     71.00 108.00   1.00    4.00    --  112.00-111.00 -90.00   37
 15  ω    107.00 139.00   1.00    4.00    --  112.00 111.00  60.00   32
 16  ω    149.00 175.00   1.00    4.00    --  112.00 111.00  60.00   26
 17  ω    127.00 165.00   1.00    4.00    --  112.00  30.00  30.00   38
 18  ω     53.00 109.00   1.00    4.00    --  112.00-111.00  90.00   56
 19  ω     84.00 111.00   1.00    4.00    --  112.00  61.00  90.00   27
 20  ω     42.00 108.00   1.00    4.00    --  112.00-111.00-150.00   66
 21  ω     78.00 103.00   1.00    4.00    --  112.00-111.00 150.00   25
 22  ω     53.00  94.00   1.00    4.00    --  112.00-111.00   0.00   41
 23  ω    101.00 177.00   1.00    4.00    --  112.00  61.00-120.00   76
 24  ω     36.00 109.00   1.00    4.00    --  112.00-111.00-180.00   73
 25  ω     36.00  68.00   1.00    4.00    --  112.00-111.00 150.00   32
 26  ω     36.00  61.00   1.00    4.00    --  112.00 -94.00  30.00   25
 27  ω     82.00 109.00   1.00    4.00    --  112.00-111.00 120.00   27
 28  ω     86.00 113.00   1.00    4.00    --  112.00  30.00  30.00   27
 29  ω     37.00  88.00   1.00    4.00    --  112.00-111.00 -60.00   51
 30  ω     68.00 109.00   1.00    4.00    --  112.00-111.00 -30.00   41
 31  ω     63.00 135.00   1.00    4.00    --  112.00 178.00 -30.00   72
 32  ω     83.00 171.00   1.00    4.00    --  112.00  61.00 -60.00   88
 33  ω    113.00 155.00   1.00    4.00    --  112.00  30.00 -60.00   42
 34  ω    119.00 146.00   1.00    4.00    --  112.00  61.00  90.00   27
 35  ω     36.00  63.00   1.00    4.00    --  112.00-111.00-120.00   27
 36  ω     69.00 108.00   1.00    4.00    --  112.00-111.00  30.00   39
 37  ω     66.00 118.00   1.00    4.00    --  112.00 178.00  90.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0888151000
_diffrn_orient_matrix_UB_12      -0.0738516000
_diffrn_orient_matrix_UB_13      -0.0583107000
_diffrn_orient_matrix_UB_21      0.0435588000
_diffrn_orient_matrix_UB_22      0.0441369000
_diffrn_orient_matrix_UB_23      -0.1007951000
_diffrn_orient_matrix_UB_31      0.1349445000
_diffrn_orient_matrix_UB_32      -0.0628288000
_diffrn_orient_matrix_UB_33      -0.0020951000
_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                3433
_reflns_number_total             3665
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.41.76a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.76a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.76a (Rigaku OD, 2020)'
_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, 2015)'
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3665
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0378
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0630P)²+0.3431P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1065
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C16(H16)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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_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 0.82723(7) 0.52160(5) 0.86647(5) 0.04359(19) Uani 1 1 d . . . . .
F2 F 0.73846(8) 0.43087(5) 0.74916(5) 0.04187(18) Uani 1 1 d . . . . .
F3 F 0.85105(7) 0.66147(5) 0.73965(5) 0.04282(18) Uani 1 1 d . . . . .
F4 F 0.95237(7) 0.53525(6) 0.68769(6) 0.0468(2) Uani 1 1 d . . . . .
N1 N 0.59530(10) 0.54733(7) 0.79543(7) 0.0340(2) Uani 1 1 d . . . . .
N2 N 0.58560(10) 0.60785(7) 0.86567(7) 0.0341(2) Uani 1 1 d . . . . .
N3 N 0.45460(10) 0.63697(7) 0.88326(8) 0.0381(2) Uani 1 1 d . . . . .
C1 C 0.74178(12) 0.52064(8) 0.78128(8) 0.0344(2) Uani 1 1 d . . . . .
C2 C 0.81995(11) 0.57687(8) 0.69959(9) 0.0351(2) Uani 1 1 d . . . . .
C3 C 0.73989(12) 0.58215(8) 0.59890(8) 0.0347(2) Uani 1 1 d . . . . .
C4 C 0.76619(15) 0.51131(9) 0.53281(10) 0.0437(3) Uani 1 1 d . . . . .
H4 H 0.834138 0.464567 0.551671 0.052 Uiso 1 1 calc R U . . .
C5 C 0.69466(18) 0.50634(11) 0.43758(10) 0.0546(3) Uani 1 1 d . . . . .
H5 H 0.714542 0.456665 0.392992 0.065 Uiso 1 1 calc R U . . .
C6 C 0.59742(17) 0.57257(11) 0.40972(10) 0.0526(3) Uani 1 1 d . . . . .
H6 H 0.549407 0.568922 0.345462 0.063 Uiso 1 1 calc R U . . .
C7 C 0.56656(13) 0.64703(9) 0.47514(10) 0.0432(3) Uani 1 1 d . . . . .
C8 C 0.46469(14) 0.71566(11) 0.44500(11) 0.0525(3) Uani 1 1 d . . . . .
H8 H 0.416164 0.710555 0.381047 0.063 Uiso 1 1 calc R U . . .
C9 C 0.43502(14) 0.78857(11) 0.50568(13) 0.0571(4) Uani 1 1 d . . . . .
H9 H 0.366927 0.834256 0.484011 0.068 Uiso 1 1 calc R U . . .
C10 C 0.50590(15) 0.79621(10) 0.60126(12) 0.0512(3) Uani 1 1 d . . . . .
H10 H 0.485692 0.847698 0.643260 0.061 Uiso 1 1 calc R U . . .
C11 C 0.60330(13) 0.73054(9) 0.63433(10) 0.0414(3) Uani 1 1 d . . . . .
H11 H 0.648392 0.736427 0.699364 0.050 Uiso 1 1 calc R U . . .
C12 C 0.63765(11) 0.65348(8) 0.57211(9) 0.0354(2) Uani 1 1 d . . . . .
C13 C 0.44396(13) 0.70604(9) 0.96516(10) 0.0439(3) Uani 1 1 d . . . . .
H13 H 0.338590 0.719380 0.974073 0.053 Uiso 1 1 calc R U . . .
C14 C 0.51618(17) 0.79590(10) 0.93608(14) 0.0601(4) Uani 1 1 d . . . . .
H14A H 0.619968 0.785148 0.926717 0.090 Uiso 1 1 calc R U . . .
H14B H 0.503548 0.841683 0.989769 0.090 Uiso 1 1 calc R U . . .
H14C H 0.471811 0.819060 0.872922 0.090 Uiso 1 1 calc R U . . .
C15 C 0.50406(17) 0.66833(11) 1.06497(11) 0.0556(4) Uani 1 1 d . . . . .
H15A H 0.458944 0.608406 1.078904 0.083 Uiso 1 1 calc R U . . .
H15B H 0.482599 0.711816 1.119411 0.083 Uiso 1 1 calc R U . . .
H15C H 0.609372 0.660463 1.060944 0.083 Uiso 1 1 calc R U . . .
C16 C 0.32291(12) 0.60280(10) 0.82869(10) 0.0438(3) Uani 1 1 d . . . . .
H16 H 0.354345 0.557981 0.776001 0.053 Uiso 1 1 calc R U . . .
C17 C 0.24365(15) 0.68167(12) 0.77552(12) 0.0561(4) Uani 1 1 d . . . . .
H17A H 0.211071 0.726428 0.825730 0.084 Uiso 1 1 calc R U . . .
H17B H 0.159396 0.657236 0.737506 0.084 Uiso 1 1 calc R U . . .
H17C H 0.309262 0.712291 0.728964 0.084 Uiso 1 1 calc R U . . .
C18 C 0.22557(15) 0.55092(11) 0.90155(13) 0.0557(4) Uani 1 1 d . . . . .
H18A H 0.281153 0.501130 0.934674 0.084 Uiso 1 1 calc R U . . .
H18B H 0.142542 0.524452 0.863899 0.084 Uiso 1 1 calc R U . . .
H18C H 0.190675 0.593947 0.952752 0.084 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 C1 1.3587(13) . ?
F2 C1 1.3649(13) . ?
F3 C2 1.3599(13) . ?
F4 C2 1.3732(12) . ?
N1 N2 1.2812(13) . ?
N1 C1 1.4210(13) . ?
N2 N3 1.3051(13) . ?
N3 C13 1.4785(15) . ?
N3 C16 1.4809(15) . ?
C1 C2 1.5455(16) . ?
C2 C3 1.5085(15) . ?
C3 C4 1.3720(17) . ?
C3 C12 1.4347(16) . ?
C4 H4 0.9500 . ?
C4 C5 1.4091(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.356(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.415(2) . ?
C7 C8 1.4156(19) . ?
C7 C12 1.4290(17) . ?
C8 H8 0.9500 . ?
C8 C9 1.357(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.413(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.3701(18) . ?
C11 H11 0.9500 . ?
C11 C12 1.4252(17) . ?
C13 H13 1.0000 . ?
C13 C14 1.5132(19) . ?
C13 C15 1.520(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16 1.0000 . ?
C16 C17 1.517(2) . ?
C16 C18 1.5302(19) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C1 111.42(9) . . ?
N1 N2 N3 115.57(9) . . ?
N2 N3 C13 115.31(9) . . ?
N2 N3 C16 123.76(10) . . ?
C13 N3 C16 120.90(9) . . ?
F1 C1 F2 106.03(9) . . ?
F1 C1 N1 114.84(9) . . ?
F1 C1 C2 107.74(9) . . ?
F2 C1 N1 106.57(9) . . ?
F2 C1 C2 106.77(9) . . ?
N1 C1 C2 114.27(9) . . ?
F3 C2 F4 105.03(9) . . ?
F3 C2 C1 107.28(9) . . ?
F3 C2 C3 113.11(9) . . ?
F4 C2 C1 106.36(9) . . ?
F4 C2 C3 109.67(9) . . ?
C3 C2 C1 114.74(9) . . ?
C4 C3 C2 115.80(10) . . ?
C4 C3 C12 120.26(11) . . ?
C12 C3 C2 123.90(10) . . ?
C3 C4 H4 119.3 . . ?
C3 C4 C5 121.48(13) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.87(13) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C7 120.82(12) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 C8 120.17(13) . . ?
C6 C7 C12 120.31(12) . . ?
C8 C7 C12 119.52(13) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.29(13) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.67(12) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.05(14) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.65(13) . . ?
C12 C11 H11 119.7 . . ?
C7 C12 C3 117.26(11) . . ?
C11 C12 C3 124.93(11) . . ?
C11 C12 C7 117.80(11) . . ?
N3 C13 H13 107.4 . . ?
N3 C13 C14 110.77(11) . . ?
N3 C13 C15 111.45(11) . . ?
C14 C13 H13 107.4 . . ?
C14 C13 C15 112.07(13) . . ?
C15 C13 H13 107.4 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 H16 107.9 . . ?
N3 C16 C17 110.77(11) . . ?
N3 C16 C18 110.02(11) . . ?
C17 C16 H16 107.9 . . ?
C17 C16 C18 112.17(11) . . ?
C18 C16 H16 107.9 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
F1 C1 C2 F3 -53.96(11) . . . . ?
F1 C1 C2 F4 58.03(11) . . . . ?
F1 C1 C2 C3 179.47(9) . . . . ?
F2 C1 C2 F3 -167.48(8) . . . . ?
F2 C1 C2 F4 -55.50(11) . . . . ?
F2 C1 C2 C3 65.94(11) . . . . ?
F3 C2 C3 C4 148.93(10) . . . . ?
F3 C2 C3 C12 -33.36(14) . . . . ?
F4 C2 C3 C4 32.07(14) . . . . ?
F4 C2 C3 C12 -150.23(10) . . . . ?
N1 N2 N3 C13 179.36(10) . . . . ?
N1 N2 N3 C16 1.12(16) . . . . ?
N1 C1 C2 F3 74.95(11) . . . . ?
N1 C1 C2 F4 -173.07(9) . . . . ?
N1 C1 C2 C3 -51.63(13) . . . . ?
N2 N1 C1 F1 32.44(13) . . . . ?
N2 N1 C1 F2 149.52(9) . . . . ?
N2 N1 C1 C2 -92.79(11) . . . . ?
N2 N3 C13 C14 66.62(15) . . . . ?
N2 N3 C13 C15 -58.89(14) . . . . ?
N2 N3 C16 C17 -120.88(13) . . . . ?
N2 N3 C16 C18 114.54(13) . . . . ?
C1 N1 N2 N3 179.46(9) . . . . ?
C1 C2 C3 C4 -87.55(12) . . . . ?
C1 C2 C3 C12 90.15(13) . . . . ?
C2 C3 C4 C5 177.85(12) . . . . ?
C2 C3 C12 C7 -177.72(10) . . . . ?
C2 C3 C12 C11 3.11(17) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C4 C3 C12 C7 -0.11(16) . . . . ?
C4 C3 C12 C11 -179.29(11) . . . . ?
C4 C5 C6 C7 0.0(2) . . . . ?
C5 C6 C7 C8 -179.97(13) . . . . ?
C5 C6 C7 C12 -0.1(2) . . . . ?
C6 C7 C8 C9 -178.89(12) . . . . ?
C6 C7 C12 C3 0.13(17) . . . . ?
C6 C7 C12 C11 179.37(11) . . . . ?
C7 C8 C9 C10 -0.52(19) . . . . ?
C8 C7 C12 C3 -179.99(10) . . . . ?
C8 C7 C12 C11 -0.75(16) . . . . ?
C8 C9 C10 C11 -0.69(19) . . . . ?
C9 C10 C11 C12 1.16(19) . . . . ?
C10 C11 C12 C3 178.76(11) . . . . ?
C10 C11 C12 C7 -0.42(17) . . . . ?
C12 C3 C4 C5 0.05(19) . . . . ?
C12 C7 C8 C9 1.24(19) . . . . ?
C13 N3 C16 C17 60.98(15) . . . . ?
C13 N3 C16 C18 -63.61(15) . . . . ?
C16 N3 C13 C14 -115.09(13) . . . . ?
C16 N3 C13 C15 119.41(13) . . . . ?

_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.841
_oxdiff_exptl_absorpt_empirical_full_min 0.564
####################################################################### 
# 
# 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_jft-r478
_database_code_depnum_ccdc_archive 'CCDC 2100359'
loop_
_audit_author_name
_audit_author_address
'Farzaneh Fadaei Tirani'
;EPFL
Switzerland
;
_audit_update_record             
;
2022-01-13 deposited with the CCDC.	2022-02-09 downloaded from the CCDC.
;
_audit_creation_date             2021-07-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H21 F2 N3 O'
_chemical_formula_sum            'C15 H21 F2 N3 O'
_chemical_formula_weight         297.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H21 F2 N3 O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   9.5957(2)
_cell_length_b                   9.9111(3)
_cell_length_c                   10.2433(2)
_cell_angle_alpha                104.216(2)
_cell_angle_beta                 114.117(2)
_cell_angle_gamma                101.164(2)
_cell_volume                     812.95(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8522
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      74.4200
_cell_measurement_theta_min      4.8760
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.793
_exptl_absorpt_coefficient_mu    0.783
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.685
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on Gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics
as implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             316
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 -1 -2 0.0238
-2 1 2 0.0114
1 0 0 0.1175
-1 -1 1 0.0396
1 1 -1 0.0340
0 -1 0 0.0395
0 1 0 0.0144
-1 -1 2 0.0782
-5 -3 4 0.0293
0 -2 1 0.0791
1 -2 0 0.0682
0 1 -2 0.1227

_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2.0005 -0.9968 -2.0000 -0.3961 -0.0758 -0.0724
-2.0005 0.9968 2.0000 0.3961 0.0758 0.0724
0.9991 0.0008 0.0006 -0.0769 -0.0944 0.1412
-0.9982 -1.0007 0.9982 0.0561 0.2431 -0.0157
0.9982 1.0007 -0.9982 -0.0561 -0.2431 0.0157
0.0014 -0.9994 -0.0012 -0.0946 0.1368 -0.0346
-0.0014 0.9994 0.0012 0.0946 -0.1368 0.0346
-0.9987 -1.0011 1.9982 0.1300 0.2550 0.1445
-4.9933 -3.0041 3.9934 0.3960 0.9300 -0.1693
0.0023 -1.9993 0.9977 -0.1153 0.2856 0.0910
1.0018 -1.9980 -0.0017 -0.2661 0.1793 0.0721
-0.0004 1.0003 -1.9989 -0.0531 -0.1607 -0.2857

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0085
_diffrn_reflns_av_unetI/netI     0.0094
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12419
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.125
_diffrn_reflns_theta_min         4.880
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     44.00  88.00   0.50    0.50    --   65.75  15.00 120.00   88
  2  ω     49.00  88.00   0.50    1.00    --   76.97  15.00  90.00   78
  3  ω     54.00 108.00   0.50    1.00    --   76.97  15.00  30.00  108
  4  ω     67.00  93.00   0.50    1.00    --   76.97  15.00 -30.00   52
  5  ω     65.00 110.00   0.50    1.00    --   76.97   0.00 -90.00   90
  6  ω     40.00 106.00   0.50    0.50    --   65.75  15.00-120.00  132
  7  ω     39.00 100.00   0.50    0.50    --   65.75   0.00-150.00  122
  8  ω     53.00 117.00   0.50    1.00    --   76.97  15.00-180.00  128
  9  ω     39.00  86.00   0.50    0.50    --   65.75   0.00 -90.00   94
 10  ω     43.00  97.00   0.50    0.50    --   65.75   0.00 -30.00  108
 11  ω     49.00 108.00   0.50    1.00    --   76.97   0.00 -30.00  118
 12  ω     40.00  91.00   0.50    1.00    --   76.97-111.00  77.00  102
 13  ω     52.00  93.00   0.50    1.00    --   76.97-125.00 150.00   82
 14  ω     73.00  98.00   0.50    0.50    --   73.19-125.00 120.00   50
 15  ω     55.00 102.00   0.50    1.00    --   76.97-125.00  60.00   94
 16  ω     42.00  71.00   0.50    1.00    --   76.97-125.00  30.00   58
 17  ω     36.00 101.00   0.50    1.00    --   76.97-125.00 -30.00  130
 18  ω     31.00  63.00   0.50    0.50    --   65.75-125.00 -60.00   64
 19  ω     52.00 102.00   0.50    1.00    --   76.97-125.00   0.00  100
 20  ω     42.00 100.00   0.50    1.00    --   76.97-125.00 -60.00  116
 21  ω     37.00 101.00   0.50    1.00    --   76.97-125.00 -90.00  128
 22  ω     36.00 101.00   0.50    1.00    --   76.97-125.00-150.00  130
 23  ω     49.00 102.00   0.50    1.00    --   76.97-125.00-180.00  106
 24  ω     71.00 102.00   0.50    1.00    --   76.97-125.00-120.00   62
 25  ω     41.00  66.00   0.50    1.00    --   76.97-125.00-120.00   50
 26  ω     76.00 102.00   0.50    1.00    --   76.97-125.00  30.00   52
 27  ω     38.00  63.00   0.50    0.50    --   73.19-111.00  77.00   50
 28  ω     35.00  79.00   0.50    0.50    --   65.75-111.00  77.00   88
 29  ω     36.00 102.00   0.50    1.00    --   76.97-125.00 120.00  132
 30  ω   -111.00 -62.00   0.50    0.50    --  -73.25 147.00 125.61   98
 31  ω   -108.00 -79.00   0.50    0.50    --  -73.25 146.00  73.70   58
 32  ω    -64.00 -38.00   0.50    0.50    --  -67.30 125.00  60.00   52
 33  ω    -80.00 -55.00   0.50    0.50    --  -67.30 111.00 171.00   50
 34  ω    -92.00 -28.00   0.50    0.50    --  -67.30 125.00 -60.00  128
 35  ω    -92.00 -46.00   0.50    0.50    --  -67.30 125.00 -90.00   92
 36  ω    -92.00 -58.00   0.50    0.50    --  -67.30 125.00-120.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0770561000
_diffrn_orient_matrix_UB_12      0.0944699000
_diffrn_orient_matrix_UB_13      0.0738742000
_diffrn_orient_matrix_UB_21      -0.0943365000
_diffrn_orient_matrix_UB_22      -0.1370443000
_diffrn_orient_matrix_UB_23      0.0118288000
_diffrn_orient_matrix_UB_31      0.1412205000
_diffrn_orient_matrix_UB_32      0.0345936000
_diffrn_orient_matrix_UB_33      0.1602057000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3033
_reflns_number_total             3276
_reflns_odcompleteness_completeness 98.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_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, 2015)'
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0030(5)
_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   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         3276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0356
_refine_ls_restrained_S_all      1.060
_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)+(0.0433P)²+0.2384P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.0948
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C13(H13)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,
 H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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_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 0.49832(8) 0.28352(8) 0.81733(9) 0.0406(2) Uani 1 1 d . . . . .
F2 F 0.31896(10) 0.07292(8) 0.64205(10) 0.0475(2) Uani 1 1 d . . . . .
O1 O 0.20355(12) 0.21152(9) 0.45655(10) 0.0423(2) Uani 1 1 d . . . . .
N1 N 0.34780(11) 0.43982(10) 0.66187(10) 0.0256(2) Uani 1 1 d . . . . .
N2 N 0.28940(10) 0.50105(9) 0.56150(10) 0.0248(2) Uani 1 1 d . . . . .
N3 N 0.33925(10) 0.64294(9) 0.61528(10) 0.0242(2) Uani 1 1 d . . . . .
C1 C 0.28697(13) 0.28751(12) 0.59096(13) 0.0281(2) Uani 1 1 d . . . . .
C2 C 0.33480(14) 0.21549(12) 0.71302(14) 0.0321(3) Uani 1 1 d . . . . .
C3 C 0.23680(13) 0.22019(12) 0.79587(13) 0.0277(2) Uani 1 1 d . . . . .
C4 C 0.10616(14) 0.09844(12) 0.75502(14) 0.0325(3) Uani 1 1 d . . . . .
H4 H 0.079623 0.008988 0.675512 0.039 Uiso 1 1 calc R U . . .
C5 C 0.01512(14) 0.10785(13) 0.83027(14) 0.0355(3) Uani 1 1 d . . . . .
H5 H -0.073753 0.024215 0.801572 0.043 Uiso 1 1 calc R U . . .
C6 C 0.05102(15) 0.23722(13) 0.94706(14) 0.0346(3) Uani 1 1 d . . . . .
C7 C 0.18103(14) 0.35898(13) 0.98529(13) 0.0332(3) Uani 1 1 d . . . . .
H7 H 0.206966 0.448767 1.064081 0.040 Uiso 1 1 calc R U . . .
C8 C 0.27245(13) 0.35124(12) 0.91072(13) 0.0298(2) Uani 1 1 d . . . . .
H8 H 0.359852 0.435494 0.937813 0.036 Uiso 1 1 calc R U . . .
C9 C -0.04623(19) 0.24672(17) 1.03081(19) 0.0519(4) Uani 1 1 d . . . . .
H9A H 0.013103 0.237661 1.130237 0.078 Uiso 1 1 calc R U . . .
H9B H -0.150632 0.166715 0.969638 0.078 Uiso 1 1 calc R U . . .
H9C H -0.064492 0.341973 1.047084 0.078 Uiso 1 1 calc R U . . .
C10 C 0.45487(14) 0.73466(12) 0.77838(13) 0.0323(3) Uani 1 1 d . . . . .
H10 H 0.504016 0.669080 0.829186 0.039 Uiso 1 1 calc R U . . .
C11 C 0.3625(2) 0.79325(17) 0.85548(16) 0.0529(4) Uani 1 1 d . . . . .
H11A H 0.314134 0.859159 0.808759 0.079 Uiso 1 1 calc R U . . .
H11B H 0.436706 0.847880 0.965142 0.079 Uiso 1 1 calc R U . . .
H11C H 0.276780 0.710615 0.842435 0.079 Uiso 1 1 calc R U . . .
C12 C 0.59092(17) 0.85495(15) 0.79288(17) 0.0488(4) Uani 1 1 d . . . . .
H12A H 0.641435 0.810855 0.735478 0.073 Uiso 1 1 calc R U . . .
H12B H 0.672012 0.906220 0.901290 0.073 Uiso 1 1 calc R U . . .
H12C H 0.547242 0.925503 0.751255 0.073 Uiso 1 1 calc R U . . .
C13 C 0.26243(13) 0.71182(12) 0.50391(13) 0.0291(2) Uani 1 1 d . . . . .
H13 H 0.294281 0.819371 0.562609 0.035 Uiso 1 1 calc R U . . .
C14 C 0.3259(2) 0.6979(2) 0.38998(18) 0.0567(4) Uani 1 1 d . . . . .
H14A H 0.443587 0.746193 0.444886 0.085 Uiso 1 1 calc R U . . .
H14B H 0.275592 0.745196 0.318178 0.085 Uiso 1 1 calc R U . . .
H14C H 0.299603 0.593287 0.333017 0.085 Uiso 1 1 calc R U . . .
C15 C 0.07970(16) 0.64749(18) 0.42748(19) 0.0517(4) Uani 1 1 d . . . . .
H15A H 0.044748 0.542112 0.367748 0.077 Uiso 1 1 calc R U . . .
H15B H 0.031071 0.698408 0.359123 0.077 Uiso 1 1 calc R U . . .
H15C H 0.045046 0.660322 0.506107 0.077 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C2 1.3873(14) . ?
F2 C2 1.3675(13) . ?
O1 C1 1.2084(14) . ?
N1 N2 1.3064(13) . ?
N1 C1 1.3860(13) . ?
N2 N3 1.2859(12) . ?
N3 C10 1.4823(13) . ?
N3 C13 1.4836(14) . ?
C1 C2 1.5426(16) . ?
C2 C3 1.5022(16) . ?
C3 C4 1.3929(15) . ?
C3 C8 1.3916(16) . ?
C4 H4 0.9500 . ?
C4 C5 1.3830(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.3902(17) . ?
C6 C7 1.3970(17) . ?
C6 C9 1.5047(18) . ?
C7 H7 0.9500 . ?
C7 C8 1.3798(17) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10 1.0000 . ?
C10 C11 1.5144(19) . ?
C10 C12 1.5164(18) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13 1.0000 . ?
C13 C14 1.5119(17) . ?
C13 C15 1.5146(17) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C1 110.08(9) . . ?
N3 N2 N1 115.20(8) . . ?
N2 N3 C10 124.04(9) . . ?
N2 N3 C13 115.03(8) . . ?
C10 N3 C13 120.77(8) . . ?
O1 C1 N1 129.90(11) . . ?
O1 C1 C2 120.21(10) . . ?
N1 C1 C2 109.84(9) . . ?
F1 C2 C1 109.37(9) . . ?
F1 C2 C3 110.07(9) . . ?
F2 C2 F1 105.13(9) . . ?
F2 C2 C1 108.08(9) . . ?
F2 C2 C3 110.50(9) . . ?
C3 C2 C1 113.34(9) . . ?
C4 C3 C2 121.37(10) . . ?
C8 C3 C2 119.20(10) . . ?
C8 C3 C4 119.35(11) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 119.96(11) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.34(11) . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C7 118.03(11) . . ?
C5 C6 C9 121.36(11) . . ?
C7 C6 C9 120.61(12) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.21(11) . . ?
C8 C7 H7 119.4 . . ?
C3 C8 H8 120.0 . . ?
C7 C8 C3 120.09(10) . . ?
C7 C8 H8 120.0 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 C10 H10 107.7 . . ?
N3 C10 C11 108.91(10) . . ?
N3 C10 C12 111.22(10) . . ?
C11 C10 H10 107.7 . . ?
C11 C10 C12 113.34(11) . . ?
C12 C10 H10 107.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 H13 107.6 . . ?
N3 C13 C14 110.28(10) . . ?
N3 C13 C15 110.60(9) . . ?
C14 C13 H13 107.6 . . ?
C14 C13 C15 112.82(12) . . ?
C15 C13 H13 107.6 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
F1 C2 C3 C4 -137.95(11) . . . . ?
F1 C2 C3 C8 45.26(13) . . . . ?
F2 C2 C3 C4 -22.27(15) . . . . ?
F2 C2 C3 C8 160.94(10) . . . . ?
O1 C1 C2 F1 134.86(11) . . . . ?
O1 C1 C2 F2 20.91(14) . . . . ?
O1 C1 C2 C3 -101.92(12) . . . . ?
N1 N2 N3 C10 0.18(14) . . . . ?
N1 N2 N3 C13 -175.15(8) . . . . ?
N1 C1 C2 F1 -47.42(12) . . . . ?
N1 C1 C2 F2 -161.37(9) . . . . ?
N1 C1 C2 C3 75.80(11) . . . . ?
N2 N1 C1 O1 6.16(16) . . . . ?
N2 N1 C1 C2 -171.28(8) . . . . ?
N2 N3 C10 C11 -103.47(12) . . . . ?
N2 N3 C10 C12 130.91(11) . . . . ?
N2 N3 C13 C14 -73.44(13) . . . . ?
N2 N3 C13 C15 52.05(13) . . . . ?
C1 N1 N2 N3 -179.50(8) . . . . ?
C1 C2 C3 C4 99.21(12) . . . . ?
C1 C2 C3 C8 -77.58(13) . . . . ?
C2 C3 C4 C5 -177.90(11) . . . . ?
C2 C3 C8 C7 178.22(10) . . . . ?
C3 C4 C5 C6 -0.01(19) . . . . ?
C4 C3 C8 C7 1.37(17) . . . . ?
C4 C5 C6 C7 0.87(19) . . . . ?
C4 C5 C6 C9 -178.94(12) . . . . ?
C5 C6 C7 C8 -0.61(18) . . . . ?
C6 C7 C8 C3 -0.50(18) . . . . ?
C8 C3 C4 C5 -1.12(17) . . . . ?
C9 C6 C7 C8 179.19(12) . . . . ?
C10 N3 C13 C14 111.07(13) . . . . ?
C10 N3 C13 C15 -123.44(12) . . . . ?
C13 N3 C10 C11 71.60(13) . . . . ?
C13 N3 C10 C12 -54.02(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.275
_oxdiff_exptl_absorpt_empirical_full_min 0.839
