# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_syu374_auto
_database_code_depnum_ccdc_archive 'CCDC 2277724'
loop_
_audit_author_name
_audit_author_address
'Ryohei Doi'
;Osaka University
Japan
;
_audit_update_record             
;
2023-06-29 deposited with the CCDC.	2023-08-30 downloaded from the CCDC.
;
_audit_creation_date             2023-06-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H9 F4 N'
_chemical_formula_sum            'C15 H9 F4 N'
_chemical_formula_weight         279.23
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H9F4N
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/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                   13.8964(3)
_cell_length_b                   5.82860(10)
_cell_length_c                   14.9634(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.679(2)
_cell_angle_gamma                90
_cell_volume                     1211.90(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6882
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      77.0660
_cell_measurement_theta_min      5.9310
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.162
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85051
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12705
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.248
_diffrn_reflns_theta_min         5.915
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -19.00   8.00   0.50    0.05    --   47.45 -77.00 150.00   54
  2  ω     14.00  70.00   0.50    0.05    --   47.45 -77.00 150.00  112
  3  ω     52.00 120.00   0.50    0.05    --   47.45  57.00   0.00  136
  4  ω     96.00 122.00   0.50    0.21    --   86.25 110.00  17.00   52
  5  ω    -19.00  19.00   0.50    0.05    --   47.45 -37.00-180.00   76
  6  ω    -27.00  -2.00   0.50    0.05    --   47.45 -19.00-150.00   50
  7  ω    -10.00  20.00   0.50    0.05    --   47.45 -37.00-150.00   60
  8  ω    -27.00   5.00   0.50    0.05    --   47.45 -19.00-120.00   64
  9  ω    -23.00   5.00   0.50    0.05    --   47.45 -19.00  90.00   56
 10  ω     17.00  42.00   0.50    0.21    --   86.25 -57.00  90.00   50
 11  ω     16.00  44.00   0.50    0.21    --   86.25 -57.00  30.00   56
 12  ω     15.00  42.00   0.50    0.21    --   86.25 -57.00 -90.00   54
 13  ω   -107.00 -81.00   0.50    0.21    -- -107.75 125.00 -60.00   52
 14  ω    -71.00 -38.00   0.50    0.21    -- -107.75 125.00-120.00   66
 15  ω   -106.00 -80.00   0.50    0.21    -- -107.75 125.00-120.00   52
 16  ω   -103.00 -53.00   0.50    0.21    -- -107.75 125.00  30.00  100
 17  ω    -65.00 -40.00   0.50    0.21    -- -107.75 137.00  55.09   50
 18  ω   -120.00 -95.00   0.50    0.21    -- -107.75 137.00  55.09   50
 19  ω    -84.00 -10.00   0.50    0.05    --  -47.45 110.00  17.00  148
 20  ω    -98.00 -62.00   0.50    0.21    -- -107.75 125.00 150.00   72
 21  ω   -110.00 -84.00   0.50    0.21    -- -107.75 125.00  90.00   52
 22  ω   -111.00 -86.00   0.50    0.21    -- -107.75 125.00  60.00   50
 23  ω   -107.00 -81.00   0.50    0.21    -- -107.75 110.00  17.00   52
 24  ω    -63.00 -37.00   0.50    0.21    -- -107.75  37.00 -90.00   52
 25  ω    -76.00 -35.00   0.50    0.21    -- -107.75  77.00  30.00   82
 26  ω   -123.00 -81.00   0.50    0.21    -- -107.75  77.00  30.00   84
 27  ω   -126.00 -97.00   0.50    0.21    -- -107.75  77.00 -60.00   58
 28  ω    -81.00 -55.00   0.50    0.21    -- -107.75  77.00 -60.00   52
 29  ω    -87.00 -37.00   0.50    0.21    -- -107.75  57.00-180.00  100
 30  ω    -77.00 -35.00   0.50    0.21    -- -107.75  57.00 -90.00   84
 31  ω    -73.00 -40.00   0.50    0.21    -- -107.75  57.00  30.00   66
 32  ω    -60.00 -35.00   0.50    0.21    -- -107.75  37.00  60.00   50
 33  ω    -87.00 -50.00   0.50    0.21    -- -107.75  57.00 150.00   74
 34  ω     10.00  45.00   0.50    0.05    --   47.45-110.00 -78.00   70
 35  ω     39.00  66.00   0.50    0.21    --   86.25-110.00 -78.00   54
 36  ω    -63.00 -34.00   0.50    0.21    -- -107.75  37.00-120.00   58
 37  ω    -60.00 -34.00   0.50    0.21    -- -107.75  37.00   0.00   52
 38  ω   -175.00-101.00   0.50    0.21    -- -107.75 -19.00  60.00  148
 39  ω   -171.00 -95.00   0.50    0.21    -- -107.75 -37.00 150.00  152
 40  ω   -138.00 -86.00   0.50    0.21    -- -107.75 -77.00  60.00  104
 41  ω   -177.00 -96.00   0.50    0.21    -- -107.75 -37.00-180.00  162
 42  ω   -153.00-125.00   0.50    0.21    -- -107.75-110.00 -78.00   56
 43  ω   -107.00 -82.00   0.50    0.21    -- -107.75-110.00 -78.00   50
 44  ω   -117.00 -74.00   0.50    0.21    -- -107.75-125.00 -30.00   86
 45  ω   -170.00-144.00   0.50    0.21    -- -107.75-125.00 -30.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0589200000
_diffrn_orient_matrix_UB_12      0.0042586000
_diffrn_orient_matrix_UB_13      -0.0865274000
_diffrn_orient_matrix_UB_21      0.0847702000
_diffrn_orient_matrix_UB_22      0.1114815000
_diffrn_orient_matrix_UB_23      0.0511325000
_diffrn_orient_matrix_UB_31      0.0404595000
_diffrn_orient_matrix_UB_32      -0.2396125000
_diffrn_orient_matrix_UB_33      0.0223004000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2006
_reflns_number_total             2209
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0345
_refine_ls_restrained_S_all      1.053
_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)+(0.0506P)²+0.3263P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.0955
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H),
 C00I(H00I), C00J(H00J), C00K(H00K)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F001 F 0.26358(6) 0.20235(13) 0.64638(5) 0.0279(2) Uani 1 1 d . . . . .
F002 F 0.33879(5) 0.51846(13) 0.68418(5) 0.0268(2) Uani 1 1 d . . . . .
F003 F 0.11535(5) 0.43449(14) 0.57862(5) 0.0296(2) Uani 1 1 d . . . . .
F004 F 0.18828(6) 0.76234(13) 0.59989(5) 0.0289(2) Uani 1 1 d . . . . .
N005 N 0.45607(8) 0.52439(19) 0.19837(8) 0.0278(3) Uani 1 1 d . . . . .
C006 C 0.14450(9) 0.5537(2) 0.72823(8) 0.0220(3) Uani 1 1 d . . . . .
C007 C 0.32023(9) 0.4414(2) 0.53059(8) 0.0216(3) Uani 1 1 d . . . . .
C008 C 0.42935(9) 0.5048(2) 0.27040(9) 0.0241(3) Uani 1 1 d . . . . .
C009 C 0.39350(9) 0.4818(2) 0.36016(8) 0.0232(3) Uani 1 1 d . . . . .
C00A C 0.27762(9) 0.4253(2) 0.62228(8) 0.0219(3) Uani 1 1 d . . . . .
C00B C 0.17922(9) 0.5462(2) 0.63347(8) 0.0222(3) Uani 1 1 d . . . . .
C00C C 0.30409(10) 0.2676(2) 0.46849(9) 0.0245(3) Uani 1 1 d . . . . .
H00C H 0.268794 0.138547 0.484278 0.029 Uiso 1 1 calc R U . . .
C00D C 0.09233(9) 0.3716(2) 0.76320(9) 0.0255(3) Uani 1 1 d . . . . .
H00D H 0.075328 0.247568 0.727239 0.031 Uiso 1 1 calc R U . . .
C00E C 0.41047(9) 0.6554(2) 0.42268(9) 0.0249(3) Uani 1 1 d . . . . .
H00E H 0.446021 0.784203 0.407106 0.030 Uiso 1 1 calc R U . . .
C00F C 0.37400(9) 0.6345(2) 0.50805(9) 0.0242(3) Uani 1 1 d . . . . .
H00F H 0.385331 0.748913 0.550196 0.029 Uiso 1 1 calc R U . . .
C00G C 0.16955(10) 0.7400(2) 0.78177(9) 0.0255(3) Uani 1 1 d . . . . .
H00G H 0.204271 0.861511 0.758024 0.031 Uiso 1 1 calc R U . . .
C00H C 0.34064(10) 0.2870(2) 0.38318(9) 0.0255(3) Uani 1 1 d . . . . .
H00H H 0.330104 0.171139 0.341448 0.031 Uiso 1 1 calc R U . . .
C00I C 0.09110(10) 0.5620(3) 0.90596(9) 0.0298(3) Uani 1 1 d . . . . .
H00I H 0.073481 0.564197 0.965719 0.036 Uiso 1 1 calc R U . . .
C00J C 0.14252(10) 0.7438(2) 0.87071(9) 0.0290(3) Uani 1 1 d . . . . .
H00J H 0.158896 0.868289 0.906667 0.035 Uiso 1 1 calc R U . . .
C00K C 0.06587(10) 0.3770(2) 0.85248(9) 0.0291(3) Uani 1 1 d . . . . .
H00K H 0.031059 0.255902 0.876423 0.035 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
F001 C00A 1.3633(15) . ?
F002 C00A 1.3626(15) . ?
F003 C00B 1.3667(15) . ?
F004 C00B 1.3626(15) . ?
N005 C008 1.1498(18) . ?
C006 C00B 1.5038(17) . ?
C006 C00D 1.3909(19) . ?
C006 C00G 1.3913(19) . ?
C007 C00A 1.5037(17) . ?
C007 C00C 1.3911(19) . ?
C007 C00F 1.3946(18) . ?
C008 C009 1.4443(18) . ?
C009 C00E 1.3961(19) . ?
C009 C00H 1.3977(19) . ?
C00A C00B 1.5491(18) . ?
C00C H00C 0.9300 . ?
C00C C00H 1.3841(19) . ?
C00D H00D 0.9300 . ?
C00D C00K 1.3902(19) . ?
C00E H00E 0.9300 . ?
C00E C00F 1.3852(18) . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00G C00J 1.3874(19) . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?
C00I C00J 1.386(2) . ?
C00I C00K 1.385(2) . ?
C00J H00J 0.9300 . ?
C00K H00K 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
C00D C006 C00B 120.47(11) . . ?
C00D C006 C00G 120.46(12) . . ?
C00G C006 C00B 118.99(11) . . ?
C00C C007 C00A 120.13(11) . . ?
C00C C007 C00F 120.58(12) . . ?
C00F C007 C00A 119.27(11) . . ?
N005 C008 C009 178.62(14) . . ?
C00E C009 C008 119.90(11) . . ?
C00E C009 C00H 120.59(12) . . ?
C00H C009 C008 119.51(12) . . ?
F001 C00A C007 111.09(10) . . ?
F001 C00A C00B 106.00(10) . . ?
F002 C00A F001 106.87(10) . . ?
F002 C00A C007 110.25(10) . . ?
F002 C00A C00B 106.84(10) . . ?
C007 C00A C00B 115.33(10) . . ?
F003 C00B C006 111.51(10) . . ?
F003 C00B C00A 106.63(10) . . ?
F004 C00B F003 106.34(10) . . ?
F004 C00B C006 110.67(10) . . ?
F004 C00B C00A 107.16(10) . . ?
C006 C00B C00A 114.11(10) . . ?
C007 C00C H00C 120.0 . . ?
C00H C00C C007 119.91(12) . . ?
C00H C00C H00C 120.0 . . ?
C006 C00D H00D 120.4 . . ?
C006 C00D C00K 119.28(12) . . ?
C00K C00D H00D 120.4 . . ?
C009 C00E H00E 120.2 . . ?
C00F C00E C009 119.57(12) . . ?
C00F C00E H00E 120.2 . . ?
C007 C00F H00F 120.1 . . ?
C00E C00F C007 119.79(12) . . ?
C00E C00F H00F 120.1 . . ?
C006 C00G H00G 120.1 . . ?
C00J C00G C006 119.75(12) . . ?
C00J C00G H00G 120.1 . . ?
C009 C00H H00H 120.2 . . ?
C00C C00H C009 119.55(12) . . ?
C00C C00H H00H 120.2 . . ?
C00J C00I H00I 119.9 . . ?
C00K C00I H00I 119.9 . . ?
C00K C00I C00J 120.22(13) . . ?
C00G C00J H00J 120.0 . . ?
C00I C00J C00G 119.97(13) . . ?
C00I C00J H00J 120.0 . . ?
C00D C00K H00K 119.8 . . ?
C00I C00K C00D 120.32(12) . . ?
C00I C00K H00K 119.8 . . ?

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
F001 C00A C00B F003 -59.44(12) . . . . ?
F001 C00A C00B F004 -172.99(9) . . . . ?
F001 C00A C00B C006 64.12(13) . . . . ?
F002 C00A C00B F003 -173.16(9) . . . . ?
F002 C00A C00B F004 73.29(12) . . . . ?
F002 C00A C00B C006 -49.59(13) . . . . ?
C006 C00D C00K C00I 0.1(2) . . . . ?
C006 C00G C00J C00I 0.3(2) . . . . ?
C007 C00A C00B F003 63.92(13) . . . . ?
C007 C00A C00B F004 -49.63(14) . . . . ?
C007 C00A C00B C006 -172.51(10) . . . . ?
C007 C00C C00H C009 -0.07(19) . . . . ?
C008 C009 C00E C00F 178.54(12) . . . . ?
C008 C009 C00H C00C -178.30(12) . . . . ?
C009 C00E C00F C007 -0.42(19) . . . . ?
C00A C007 C00C C00H 177.74(12) . . . . ?
C00A C007 C00F C00E -177.51(11) . . . . ?
C00B C006 C00D C00K 176.33(12) . . . . ?
C00B C006 C00G C00J -176.55(12) . . . . ?
C00C C007 C00A F001 26.73(16) . . . . ?
C00C C007 C00A F002 145.02(12) . . . . ?
C00C C007 C00A C00B -93.90(14) . . . . ?
C00C C007 C00F C00E 1.00(19) . . . . ?
C00D C006 C00B F003 34.45(16) . . . . ?
C00D C006 C00B F004 152.60(12) . . . . ?
C00D C006 C00B C00A -86.44(14) . . . . ?
C00D C006 C00G C00J 0.2(2) . . . . ?
C00E C009 C00H C00C 0.6(2) . . . . ?
C00F C007 C00A F001 -154.75(11) . . . . ?
C00F C007 C00A F002 -36.47(15) . . . . ?
C00F C007 C00A C00B 84.62(15) . . . . ?
C00F C007 C00C C00H -0.8(2) . . . . ?
C00G C006 C00B F003 -148.81(12) . . . . ?
C00G C006 C00B F004 -30.66(16) . . . . ?
C00G C006 C00B C00A 90.30(14) . . . . ?
C00G C006 C00D C00K -0.36(19) . . . . ?
C00H C009 C00E C00F -0.40(19) . . . . ?
C00J C00I C00K C00D 0.3(2) . . . . ?
C00K C00I C00J C00G -0.5(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.493
_oxdiff_exptl_absorpt_empirical_full_min 0.754
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hot hexane'
####################################################################### 
# 
# 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_syu_214_take3_auto
_database_code_depnum_ccdc_archive 'CCDC 2277726'
loop_
_audit_author_name
_audit_author_address
'Ryohei Doi'
;Osaka University
Japan
;
_audit_update_record             
;
2023-06-29 deposited with the CCDC.	2023-08-30 downloaded from the CCDC.
;
_audit_creation_date             2023-05-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H9 F6 N'
_chemical_formula_sum            'C16 H9 F6 N'
_chemical_formula_weight         329.24
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   11.2311(5)
_cell_length_b                   9.9935(3)
_cell_length_c                   13.5768(6)
_cell_angle_alpha                90
_cell_angle_beta                 113.826(5)
_cell_angle_gamma                90
_cell_volume                     1393.97(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7475
_cell_measurement_temperature    123
_cell_measurement_theta_max      76.5230
_cell_measurement_theta_min      3.5400
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.321
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0674
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16159
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.064
_diffrn_reflns_theta_max         67.064
_diffrn_reflns_theta_min         4.303
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00 -38.00   0.50    0.05    -- -105.75 125.00 120.00  144
  2  ω    -75.00 -37.00   0.50    0.05    -- -105.75 125.00  60.00   76
  3  ω   -105.00 -37.00   0.50    0.05    -- -105.75 125.00   0.00  136
  4  ω    -99.00 -62.00   0.50    0.05    -- -105.75 125.00 -60.00   74
  5  ω    -75.00 -39.00   0.50    0.05    -- -105.75 107.00-110.70   72
  6  ω   -110.00 -44.00   0.50    0.05    -- -105.75 125.00-120.00  132
  7  ω   -107.00 -79.00   0.50    0.05    -- -105.75 107.00-110.70   56
  8  ω   -108.00 -59.00   0.50    0.05    -- -105.75 109.00 -30.96   98
  9  ω    -73.00 -36.00   0.50    0.05    -- -105.75 103.00  67.67   74
 10  ω   -105.00 -80.00   0.50    0.05    -- -105.75 103.00  67.67   50
 11  ω   -106.00 -76.00   0.50    0.05    -- -105.75 107.00 107.68   60
 12  ω    -60.00 -34.00   0.50    0.05    -- -105.75  33.00  34.00   52
 13  ω    -61.00 -36.00   0.50    0.05    -- -105.75  77.00 -30.00   50
 14  ω    -67.00 -35.00   0.50    0.05    -- -105.75  57.00 -30.00   64
 15  ω    -86.00 -45.00   0.50    0.05    -- -105.75  57.00 -90.00   82
 16  ω    -73.00 -44.00   0.50    0.05    -- -105.75  57.00-120.00   58
 17  ω    -63.00 -37.00   0.50    0.05    -- -105.75  37.00-120.00   52
 18  ω   -125.00-100.00   0.50    0.05    -- -105.75  77.00 -30.00   50
 19  ω    -87.00 -62.00   0.50    0.05    -- -105.75  57.00 120.00   50
 20  ω    -62.00 -36.00   0.50    0.05    -- -105.75  37.00  60.00   52
 21  ω    -42.00  16.00   0.50    0.05    --  -49.68  33.00  34.00  116
 22  ω     15.00  42.00   0.50    0.05    --   49.68 -57.00-120.00   54
 23  ω    -10.00  16.00   0.50    0.05    --   49.68 -33.00-123.00   52
 24  ω    -20.00  10.00   0.50    0.05    --   49.68 -57.00-120.00   60
 25  ω    -17.00   9.00   0.50    0.05    --   49.68 -37.00 -30.00   52
 26  ω     46.00 120.00   0.50    0.05    --   49.68  33.00  34.00  148
 27  ω     93.00 154.00   0.50    0.05    --   82.50  33.00  34.00  122
 28  ω    -23.00   5.00   0.50    0.05    --   49.68 -19.00  90.00   56
 29  ω    -23.00   2.00   0.50    0.05    --   49.68 -19.00 120.00   50
 30  ω     11.00  42.00   0.50    0.05    --   82.50 -57.00  90.00   62
 31  ω     17.00  44.00   0.50    0.05    --   82.50 -57.00 150.00   54
 32  ω     14.00  44.00   0.50    0.05    --   82.50 -57.00  60.00   60
 33  ω     14.00  39.00   0.50    0.05    --   82.50 -57.00 -90.00   50
 34  ω     19.00  45.00   0.50    0.05    --   49.68-125.00  60.00   52
 35  ω     52.00  90.00   0.50    0.05    --   49.68-125.00  60.00   76
 36  ω     14.00  67.00   0.50    0.05    --   82.50 -99.00 150.00  106
 37  ω   -118.00 -43.00   0.50    0.05    --  -49.68 -33.00-123.00  150
 38  ω   -177.00-100.00   0.50    0.05    -- -105.75 -37.00 -30.00  154
 39  ω   -169.00-103.00   0.50    0.05    -- -105.75 -33.00-123.00  132
 40  ω   -170.00-106.00   0.50    0.05    -- -105.75 -37.00   0.00  128
 41  ω   -141.00-100.00   0.50    0.05    -- -105.75 -19.00  60.00   82
 42  ω   -136.00-109.00   0.50    0.05    -- -105.75 -37.00 120.00   54
 43  ω   -176.00-144.00   0.50    0.05    -- -105.75 -37.00 120.00   64
 44  ω   -173.00-120.00   0.50    0.05    -- -105.75-125.00  30.00  106
 45  ω   -165.00-108.00   0.50    0.05    -- -105.75 -99.00 -90.00  114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2188
_reflns_number_total             2489
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2489
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.065
_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)+(0.0627P)²+0.2668P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1083
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I),
 C00L(H00L), C00M(H00M), C00N(H00N)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F001 F 0.65064(8) 0.28720(8) 0.37421(7) 0.0299(2) Uani 1 1 d . . . . .
F002 F 0.56675(9) 0.39448(9) 0.47068(7) 0.0350(2) Uani 1 1 d . . . . .
F003 F 0.44034(9) 0.43474(11) 0.26515(8) 0.0410(3) Uani 1 1 d . . . . .
F004 F 0.84815(9) 0.46070(10) 0.42827(7) 0.0392(3) Uani 1 1 d . . . . .
F005 F 0.53376(10) 0.61574(9) 0.35076(8) 0.0433(3) Uani 1 1 d . . . . .
F006 F 0.76352(11) 0.58690(9) 0.51470(8) 0.0457(3) Uani 1 1 d . . . . .
C007 C 0.61499(15) 0.51963(14) 0.23119(12) 0.0270(3) Uani 1 1 d . . . . .
C008 C 0.63745(15) 0.40990(14) 0.41148(12) 0.0270(3) Uani 1 1 d . . . . .
C009 C 0.83790(15) 0.37284(15) 0.58616(12) 0.0286(3) Uani 1 1 d . . . . .
C00A C 0.71852(15) 0.55864(16) 0.08013(12) 0.0292(3) Uani 1 1 d . . . . .
N00B N 0.81960(17) 0.59238(17) -0.05923(13) 0.0494(4) Uani 1 1 d . . . . .
C00C C 0.65177(16) 0.44080(15) 0.07893(12) 0.0310(4) Uani 1 1 d . . . . .
H00C H 0.641921 0.373974 0.026436 0.037 Uiso 1 1 calc R U . . .
C00D C 0.55800(15) 0.49767(15) 0.31253(13) 0.0310(4) Uani 1 1 d . . . . .
C00E C 0.59986(15) 0.42146(14) 0.15453(12) 0.0292(3) Uani 1 1 d . . . . .
H00E H 0.554043 0.341381 0.154044 0.035 Uiso 1 1 calc R U . . .
C00F C 0.68158(16) 0.63730(15) 0.23232(12) 0.0329(4) Uani 1 1 d . . . . .
H00F H 0.691891 0.703949 0.285040 0.040 Uiso 1 1 calc R U . . .
C00G C 0.91859(15) 0.26775(16) 0.58627(12) 0.0317(3) Uani 1 1 d . . . . .
H00G H 0.937501 0.251571 0.525142 0.038 Uiso 1 1 calc R U . . .
C00H C 0.81087(16) 0.39741(16) 0.67593(13) 0.0336(4) Uani 1 1 d . . . . .
H00H H 0.755239 0.469263 0.675412 0.040 Uiso 1 1 calc R U . . .
C00I C 0.73261(16) 0.65676(16) 0.15646(13) 0.0337(4) Uani 1 1 d . . . . .
H00I H 0.777426 0.737374 0.156448 0.040 Uiso 1 1 calc R U . . .
C00J C 0.77459(17) 0.57772(17) 0.00260(13) 0.0362(4) Uani 1 1 d . . . . .
C00K C 0.77513(16) 0.45785(15) 0.48733(12) 0.0302(3) Uani 1 1 d . . . . .
C00L C 0.86557(16) 0.31644(19) 0.76623(13) 0.0384(4) Uani 1 1 d . . . . .
H00L H 0.848608 0.333522 0.828191 0.046 Uiso 1 1 calc R U . . .
C00M C 0.97148(16) 0.18641(18) 0.67655(14) 0.0379(4) Uani 1 1 d . . . . .
H00M H 1.026187 0.113709 0.676989 0.045 Uiso 1 1 calc R U . . .
C00N C 0.94482(16) 0.21083(19) 0.76568(14) 0.0404(4) Uani 1 1 d . . . . .
H00N H 0.981217 0.154630 0.827099 0.049 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
F001 C008 1.3573(16) . ?
F002 C008 1.3475(17) . ?
F003 C00D 1.3670(19) . ?
F004 C00K 1.3593(18) . ?
F005 C00D 1.3601(18) . ?
F006 C00K 1.3629(18) . ?
C007 C00D 1.499(2) . ?
C007 C00E 1.390(2) . ?
C007 C00F 1.390(2) . ?
C008 C00D 1.550(2) . ?
C008 C00K 1.547(2) . ?
C009 C00G 1.387(2) . ?
C009 C00H 1.392(2) . ?
C009 C00K 1.502(2) . ?
C00A C00C 1.393(2) . ?
C00A C00I 1.388(2) . ?
C00A C00J 1.441(2) . ?
N00B C00J 1.151(2) . ?
C00C H00C 0.9500 . ?
C00C C00E 1.384(2) . ?
C00E H00E 0.9500 . ?
C00F H00F 0.9500 . ?
C00F C00I 1.380(2) . ?
C00G H00G 0.9500 . ?
C00G C00M 1.388(2) . ?
C00H H00H 0.9500 . ?
C00H C00L 1.388(2) . ?
C00I H00I 0.9500 . ?
C00L H00L 0.9500 . ?
C00L C00N 1.383(3) . ?
C00M H00M 0.9500 . ?
C00M C00N 1.381(2) . ?
C00N H00N 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00E C007 C00D 119.26(13) . . ?
C00E C007 C00F 120.51(14) . . ?
C00F C007 C00D 120.23(13) . . ?
F001 C008 C00D 107.42(12) . . ?
F001 C008 C00K 107.32(12) . . ?
F002 C008 F001 107.36(11) . . ?
F002 C008 C00D 108.07(12) . . ?
F002 C008 C00K 108.04(12) . . ?
C00K C008 C00D 118.18(12) . . ?
C00G C009 C00H 120.42(14) . . ?
C00G C009 C00K 120.01(13) . . ?
C00H C009 C00K 119.54(14) . . ?
C00C C00A C00J 119.70(15) . . ?
C00I C00A C00C 120.29(14) . . ?
C00I C00A C00J 120.00(14) . . ?
C00A C00C H00C 120.1 . . ?
C00E C00C C00A 119.71(14) . . ?
C00E C00C H00C 120.1 . . ?
F003 C00D C007 109.87(12) . . ?
F003 C00D C008 104.84(12) . . ?
F005 C00D F003 105.92(12) . . ?
F005 C00D C007 111.40(12) . . ?
F005 C00D C008 107.11(12) . . ?
C007 C00D C008 116.98(12) . . ?
C007 C00E H00E 120.1 . . ?
C00C C00E C007 119.75(14) . . ?
C00C C00E H00E 120.1 . . ?
C007 C00F H00F 120.2 . . ?
C00I C00F C007 119.65(14) . . ?
C00I C00F H00F 120.2 . . ?
C009 C00G H00G 120.3 . . ?
C009 C00G C00M 119.39(14) . . ?
C00M C00G H00G 120.3 . . ?
C009 C00H H00H 120.2 . . ?
C00L C00H C009 119.70(15) . . ?
C00L C00H H00H 120.2 . . ?
C00A C00I H00I 120.0 . . ?
C00F C00I C00A 120.07(14) . . ?
C00F C00I H00I 120.0 . . ?
N00B C00J C00A 179.68(19) . . ?
F004 C00K F006 106.74(12) . . ?
F004 C00K C008 107.02(12) . . ?
F004 C00K C009 111.20(13) . . ?
F006 C00K C008 107.13(13) . . ?
F006 C00K C009 110.72(12) . . ?
C009 C00K C008 113.68(12) . . ?
C00H C00L H00L 120.1 . . ?
C00N C00L C00H 119.76(15) . . ?
C00N C00L H00L 120.1 . . ?
C00G C00M H00M 119.9 . . ?
C00N C00M C00G 120.22(16) . . ?
C00N C00M H00M 119.9 . . ?
C00L C00N H00N 119.7 . . ?
C00M C00N C00L 120.51(15) . . ?
C00M C00N H00N 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
F001 C008 C00D F003 61.69(14) . . . . ?
F001 C008 C00D F005 173.92(11) . . . . ?
F001 C008 C00D C007 -60.28(17) . . . . ?
F001 C008 C00K F004 58.95(14) . . . . ?
F001 C008 C00K F006 173.12(11) . . . . ?
F001 C008 C00K C009 -64.23(15) . . . . ?
F002 C008 C00D F003 -53.87(15) . . . . ?
F002 C008 C00D F005 58.37(15) . . . . ?
F002 C008 C00D C007 -175.83(12) . . . . ?
F002 C008 C00K F004 174.43(11) . . . . ?
F002 C008 C00K F006 -71.39(14) . . . . ?
F002 C008 C00K C009 51.26(16) . . . . ?
C007 C00F C00I C00A -0.6(2) . . . . ?
C009 C00G C00M C00N -0.6(2) . . . . ?
C009 C00H C00L C00N -1.0(2) . . . . ?
C00A C00C C00E C007 -0.1(2) . . . . ?
C00C C00A C00I C00F 0.7(2) . . . . ?
C00D C007 C00E C00C 179.85(14) . . . . ?
C00D C007 C00F C00I -179.45(14) . . . . ?
C00D C008 C00K F004 -62.58(16) . . . . ?
C00D C008 C00K F006 51.60(17) . . . . ?
C00D C008 C00K C009 174.24(12) . . . . ?
C00E C007 C00D F003 -38.09(18) . . . . ?
C00E C007 C00D F005 -155.14(13) . . . . ?
C00E C007 C00D C008 81.22(18) . . . . ?
C00E C007 C00F C00I 0.2(2) . . . . ?
C00F C007 C00D F003 141.57(14) . . . . ?
C00F C007 C00D F005 24.5(2) . . . . ?
C00F C007 C00D C008 -99.11(17) . . . . ?
C00F C007 C00E C00C 0.2(2) . . . . ?
C00G C009 C00H C00L 0.3(2) . . . . ?
C00G C009 C00K F004 -27.81(19) . . . . ?
C00G C009 C00K F006 -146.30(14) . . . . ?
C00G C009 C00K C008 93.05(17) . . . . ?
C00G C00M C00N C00L -0.1(3) . . . . ?
C00H C009 C00G C00M 0.5(2) . . . . ?
C00H C009 C00K F004 154.43(13) . . . . ?
C00H C009 C00K F006 35.94(19) . . . . ?
C00H C009 C00K C008 -84.71(17) . . . . ?
C00H C00L C00N C00M 0.9(3) . . . . ?
C00I C00A C00C C00E -0.3(2) . . . . ?
C00J C00A C00C C00E 178.89(14) . . . . ?
C00J C00A C00I C00F -178.50(15) . . . . ?
C00K C008 C00D F003 -176.84(12) . . . . ?
C00K C008 C00D F005 -64.61(16) . . . . ?
C00K C008 C00D C007 61.19(18) . . . . ?
C00K C009 C00G C00M -177.23(14) . . . . ?
C00K C009 C00H C00L 178.03(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
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hot hexane'
####################################################################### 
# 
# 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_syu_214_c4_auto
_database_code_depnum_ccdc_archive 'CCDC 2277725'
loop_
_audit_author_name
_audit_author_address
'Ryohei Doi'
;Osaka University
Japan
;
_audit_update_record             
;
2023-06-29 deposited with the CCDC.	2023-08-30 downloaded from the CCDC.
;
_audit_creation_date             2023-05-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H9 F8 N'
_chemical_formula_sum            'C17 H9 F8 N'
_chemical_formula_weight         379.25
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   22.9150(17)
_cell_length_b                   5.0800(3)
_cell_length_c                   27.5806(19)
_cell_angle_alpha                90
_cell_angle_beta                 106.035(7)
_cell_angle_gamma                90
_cell_volume                     3085.7(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3337
_cell_measurement_temperature    123
_cell_measurement_theta_max      74.9220
_cell_measurement_theta_min      4.0030
_shelx_estimated_absorpt_T_max   0.930
_shelx_estimated_absorpt_T_min   0.866
_exptl_absorpt_coefficient_mu    1.476
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (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_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0986
_diffrn_reflns_av_unetI/netI     0.0626
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            17219
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.051
_diffrn_reflns_theta_max         67.051
_diffrn_reflns_theta_min         3.335
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00  19.00   0.50    0.10    --   49.93 -37.00 120.00   72
  2  ω    -20.00  20.00   0.50    0.10    --   49.93 -37.00  90.00   80
  3  ω    -21.00   4.00   0.50    0.10    --   49.93 -19.00   0.00   50
  4  ω    -22.00   4.00   0.50    0.10    --   49.93 -19.00  30.00   52
  5  ω    -22.00   4.00   0.50    0.10    --   49.93 -19.00 -30.00   52
  6  ω    -22.00   3.00   0.50    0.10    --   49.93 -19.00 -60.00   50
  7  ω    -22.00   3.00   0.50    0.10    --   49.93 -19.00-120.00   50
  8  ω     36.00  62.00   0.50    0.10    --   82.50-111.00  36.00   52
  9  ω    -60.00   4.00   0.50    0.10    --  -49.93  57.00 120.00  128
 10  ω    -47.00 -21.00   0.50    0.10    --  -49.93  19.00-180.00   52
 11  ω     20.00  45.00   0.50    0.10    --   49.93-111.00  36.00   50
 12  ω     19.00  44.00   0.50    0.10    --   82.50 -57.00 -60.00   50
 13  ω     11.00  43.00   0.50    0.10    --   82.50 -57.00 -90.00   64
 14  ω     12.00  39.00   0.50    0.10    --   82.50 -57.00 150.00   54
 15  ω   -177.00 -99.00   0.50    0.10    -- -105.75 -37.00 120.00  156
 16  ω   -166.00-127.00   0.50    0.10    -- -105.75 -37.00 -30.00   78
 17  ω   -176.00-151.00   0.50    0.10    -- -105.75 -19.00-120.00   50
 18  ω   -145.00 -98.00   0.50    0.10    -- -105.75 -19.00-120.00   94
 19  ω   -134.00 -98.00   0.50    0.10    -- -105.75 -19.00-150.00   72
 20  ω   -168.00-138.00   0.50    0.10    -- -105.75 -19.00-150.00   60
 21  ω   -135.00 -82.00   0.50    0.10    -- -105.75-111.00  36.00  106
 22  ω    -85.00 -35.00   0.50    0.10    -- -105.75  57.00  60.00  100
 23  ω    -71.00 -46.00   0.50    0.10    -- -105.75  57.00  90.00   50
 24  ω    -79.00 -40.00   0.50    0.10    -- -105.75  57.00 120.00   78
 25  ω    -86.00 -53.00   0.50    0.10    -- -105.75  57.00 -60.00   66
 26  ω   -122.00 -72.00   0.50    0.10    -- -105.75  77.00 -90.00  100
 27  ω    -82.00 -41.00   0.50    0.10    -- -105.75  57.00-180.00   82
 28  ω    -62.00 -37.00   0.50    0.10    -- -105.75  37.00-150.00   50
 29  ω    -86.00 -37.00   0.50    0.10    -- -105.75  57.00 -90.00   98
 30  ω    -63.00 -38.00   0.50    0.10    -- -105.75  37.00 -30.00   50
 31  ω    -60.00 -35.00   0.50    0.10    -- -105.75  37.00   0.00   50
 32  ω    -63.00 -34.00   0.50    0.10    -- -105.75  37.00  60.00   58
 33  ω    -63.00 -35.00   0.50    0.10    -- -105.75  37.00 120.00   56
 34  ω    -80.00 -39.00   0.50    0.10    --  -49.93 111.00 130.00   82
 35  ω   -110.00 -85.00   0.50    0.10    -- -105.75 125.00 150.00   50
 36  ω    -79.00 -41.00   0.50    0.10    -- -105.75 125.00  60.00   76
 37  ω   -110.00 -81.00   0.50    0.10    -- -105.75 125.00  30.00   58
 38  ω    -94.00 -64.00   0.50    0.10    -- -105.75 125.00 -30.00   60
 39  ω   -110.00 -69.00   0.50    0.10    -- -105.75 125.00 -90.00   82
 40  ω    -99.00 -40.00   0.50    0.10    -- -105.75 125.00-120.00  118
 41  ω   -109.00 -37.00   0.50    0.10    -- -105.75 125.00 -60.00  144
 42  ω   -108.00 -74.00   0.50    0.10    -- -105.75 111.00 130.00   68
 43  ω    -68.00 -42.00   0.50    0.10    -- -105.75 125.00 150.00   52
 44  ω    -27.00  -2.00   0.50    0.10    --  -49.93 111.00 130.00   50
 45  ω     84.00 120.00   0.50    0.10    --   82.50 111.00 130.00   72
 46  ω     74.00 119.00   0.50    0.10    --   49.93 125.00  30.00   90
 47  ω     84.00 119.00   0.50    0.10    --   49.93 125.00 -90.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2085
_reflns_number_total             2747
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2747
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0526
_refine_ls_restrained_S_all      1.042
_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)+(0.0886P)²+1.3286P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1465
_refine_ls_wR_factor_ref         0.1598
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M),
 C00O(H00O), C00P(H00P), C00Q(H00Q)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F001 F 0.35416(7) 0.8167(3) 0.54360(5) 0.0340(4) Uani 1 1 d . . . . .
F002 F 0.31943(6) 0.3643(3) 0.49618(5) 0.0345(4) Uani 1 1 d . . . . .
F003 F 0.39696(7) 0.3613(3) 0.46454(5) 0.0349(4) Uani 1 1 d . . . . .
F004 F 0.48116(6) 0.4182(3) 0.55116(6) 0.0365(4) Uani 1 1 d . . . . .
F005 F 0.40593(7) 0.3448(3) 0.58389(5) 0.0356(4) Uani 1 1 d . . . . .
F006 F 0.42786(7) 0.8650(3) 0.50796(5) 0.0362(4) Uani 1 1 d . . . . .
F007 F 0.28183(8) 0.8301(3) 0.44730(6) 0.0470(5) Uani 1 1 d . . . . .
F008 F 0.35864(8) 0.8170(3) 0.41474(6) 0.0477(5) Uani 1 1 d . . . . .
N009 N 0.16810(11) -0.2301(6) 0.25659(10) 0.0487(7) Uani 1 1 d . . . . .
C00A C 0.46810(11) 0.7150(5) 0.61282(9) 0.0277(6) Uani 1 1 d . . . . .
C00B C 0.35823(10) 0.5179(5) 0.47991(9) 0.0265(6) Uani 1 1 d . . . . .
C00C C 0.39458(11) 0.6875(5) 0.52485(9) 0.0272(6) Uani 1 1 d . . . . .
C00D C 0.43879(11) 0.5382(5) 0.56925(9) 0.0285(6) Uani 1 1 d . . . . .
C00E C 0.28561(11) 0.4793(5) 0.39186(9) 0.0301(6) Uani 1 1 d . . . . .
C00F C 0.22495(12) 0.1165(5) 0.32146(9) 0.0311(6) Uani 1 1 d . . . . .
C00G C 0.31209(12) 0.3865(5) 0.35586(9) 0.0310(6) Uani 1 1 d . . . . .
H00G H 0.351146 0.447583 0.355491 0.037 Uiso 1 1 calc R U . . .
C00H C 0.32021(12) 0.6661(5) 0.43231(9) 0.0310(6) Uani 1 1 d . . . . .
C00I C 0.28194(12) 0.2050(5) 0.32039(9) 0.0319(6) Uani 1 1 d . . . . .
H00I H 0.300016 0.141392 0.295535 0.038 Uiso 1 1 calc R U . . .
C00J C 0.44030(12) 0.7603(5) 0.65077(10) 0.0330(6) Uani 1 1 d . . . . .
H00J H 0.403005 0.676000 0.649860 0.040 Uiso 1 1 calc R U . . .
C00K C 0.19777(12) 0.2122(5) 0.35740(10) 0.0336(6) Uani 1 1 d . . . . .
H00K H 0.158397 0.154060 0.357488 0.040 Uiso 1 1 calc R U . . .
C00L C 0.22857(12) 0.3922(5) 0.39286(10) 0.0318(6) Uani 1 1 d . . . . .
H00L H 0.210753 0.456022 0.417850 0.038 Uiso 1 1 calc R U . . .
C00M C 0.52212(12) 0.8408(5) 0.61372(10) 0.0342(6) Uani 1 1 d . . . . .
H00M H 0.540406 0.814970 0.587086 0.041 Uiso 1 1 calc R U . . .
C00N C 0.19325(12) -0.0767(6) 0.28535(10) 0.0363(6) Uani 1 1 d . . . . .
C00O C 0.46723(13) 0.9293(6) 0.69007(10) 0.0377(7) Uani 1 1 d . . . . .
H00O H 0.448070 0.963166 0.715896 0.045 Uiso 1 1 calc R U . . .
C00P C 0.52173(13) 1.0481(6) 0.69165(10) 0.0418(7) Uani 1 1 d . . . . .
H00P H 0.540486 1.160944 0.718988 0.050 Uiso 1 1 calc R U . . .
C00Q C 0.54919(13) 1.0045(6) 0.65387(11) 0.0427(7) Uani 1 1 d . . . . .
H00Q H 0.586847 1.086789 0.655290 0.051 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
F001 C00C 1.349(3) . ?
F002 C00B 1.349(3) . ?
F003 C00B 1.345(3) . ?
F004 C00D 1.353(3) . ?
F005 C00D 1.365(3) . ?
F006 C00C 1.345(3) . ?
F007 C00H 1.356(3) . ?
F008 C00H 1.354(3) . ?
N009 C00N 1.147(4) . ?
C00A C00D 1.502(3) . ?
C00A C00J 1.387(4) . ?
C00A C00M 1.387(4) . ?
C00B C00C 1.550(3) . ?
C00B C00H 1.555(3) . ?
C00C C00D 1.554(3) . ?
C00E C00G 1.382(4) . ?
C00E C00H 1.512(3) . ?
C00E C00L 1.387(4) . ?
C00F C00I 1.389(4) . ?
C00F C00K 1.396(4) . ?
C00F C00N 1.443(4) . ?
C00G H00G 0.9500 . ?
C00G C00I 1.383(4) . ?
C00I H00I 0.9500 . ?
C00J H00J 0.9500 . ?
C00J C00O 1.387(4) . ?
C00K H00K 0.9500 . ?
C00K C00L 1.382(4) . ?
C00L H00L 0.9500 . ?
C00M H00M 0.9500 . ?
C00M C00Q 1.387(4) . ?
C00O H00O 0.9500 . ?
C00O C00P 1.377(4) . ?
C00P H00P 0.9500 . ?
C00P C00Q 1.376(4) . ?
C00Q H00Q 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00J C00A C00D 120.4(2) . . ?
C00J C00A C00M 120.3(2) . . ?
C00M C00A C00D 119.3(2) . . ?
F002 C00B C00C 108.27(18) . . ?
F002 C00B C00H 107.08(19) . . ?
F003 C00B F002 108.38(19) . . ?
F003 C00B C00C 108.98(19) . . ?
F003 C00B C00H 106.55(19) . . ?
C00C C00B C00H 117.3(2) . . ?
F001 C00C C00B 107.61(19) . . ?
F001 C00C C00D 107.61(19) . . ?
F006 C00C F001 108.77(19) . . ?
F006 C00C C00B 109.06(19) . . ?
F006 C00C C00D 106.94(19) . . ?
C00B C00C C00D 116.6(2) . . ?
F004 C00D F005 107.18(19) . . ?
F004 C00D C00A 110.89(19) . . ?
F004 C00D C00C 107.90(19) . . ?
F005 C00D C00A 110.8(2) . . ?
F005 C00D C00C 106.95(19) . . ?
C00A C00D C00C 112.9(2) . . ?
C00G C00E C00H 120.0(2) . . ?
C00G C00E C00L 120.6(2) . . ?
C00L C00E C00H 119.4(2) . . ?
C00I C00F C00K 120.6(2) . . ?
C00I C00F C00N 120.1(2) . . ?
C00K C00F C00N 119.3(2) . . ?
C00E C00G H00G 119.9 . . ?
C00E C00G C00I 120.2(2) . . ?
C00I C00G H00G 119.9 . . ?
F007 C00H C00B 107.4(2) . . ?
F007 C00H C00E 111.0(2) . . ?
F008 C00H F007 107.6(2) . . ?
F008 C00H C00B 107.9(2) . . ?
F008 C00H C00E 110.6(2) . . ?
C00E C00H C00B 112.1(2) . . ?
C00F C00I H00I 120.3 . . ?
C00G C00I C00F 119.3(2) . . ?
C00G C00I H00I 120.3 . . ?
C00A C00J H00J 120.2 . . ?
C00A C00J C00O 119.6(2) . . ?
C00O C00J H00J 120.2 . . ?
C00F C00K H00K 120.3 . . ?
C00L C00K C00F 119.5(2) . . ?
C00L C00K H00K 120.3 . . ?
C00E C00L H00L 120.1 . . ?
C00K C00L C00E 119.8(2) . . ?
C00K C00L H00L 120.1 . . ?
C00A C00M H00M 120.3 . . ?
C00Q C00M C00A 119.4(2) . . ?
C00Q C00M H00M 120.3 . . ?
N009 C00N C00F 179.9(3) . . ?
C00J C00O H00O 120.0 . . ?
C00P C00O C00J 120.0(3) . . ?
C00P C00O H00O 120.0 . . ?
C00O C00P H00P 119.8 . . ?
C00Q C00P C00O 120.4(3) . . ?
C00Q C00P H00P 119.8 . . ?
C00M C00Q H00Q 119.9 . . ?
C00P C00Q C00M 120.3(3) . . ?
C00P C00Q H00Q 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F001 C00C C00D F004 -177.19(17) . . . . ?
F001 C00C C00D F005 67.8(2) . . . . ?
F001 C00C C00D C00A -54.3(3) . . . . ?
F002 C00B C00C F001 -54.5(2) . . . . ?
F002 C00B C00C F006 -172.31(18) . . . . ?
F002 C00B C00C C00D 66.5(3) . . . . ?
F002 C00B C00H F007 65.7(2) . . . . ?
F002 C00B C00H F008 -178.63(18) . . . . ?
F002 C00B C00H C00E -56.6(3) . . . . ?
F003 C00B C00C F001 -172.17(18) . . . . ?
F003 C00B C00C F006 70.0(2) . . . . ?
F003 C00B C00C C00D -51.2(3) . . . . ?
F003 C00B C00H F007 -178.53(19) . . . . ?
F003 C00B C00H F008 -62.8(2) . . . . ?
F003 C00B C00H C00E 59.2(3) . . . . ?
F006 C00C C00D F004 -60.5(2) . . . . ?
F006 C00C C00D F005 -175.49(18) . . . . ?
F006 C00C C00D C00A 62.4(3) . . . . ?
C00A C00J C00O C00P -1.0(4) . . . . ?
C00A C00M C00Q C00P -2.0(4) . . . . ?
C00B C00C C00D F004 61.9(3) . . . . ?
C00B C00C C00D F005 -53.2(3) . . . . ?
C00B C00C C00D C00A -175.3(2) . . . . ?
C00C C00B C00H F007 -56.2(3) . . . . ?
C00C C00B C00H F008 59.5(3) . . . . ?
C00C C00B C00H C00E -178.4(2) . . . . ?
C00D C00A C00J C00O -178.4(2) . . . . ?
C00D C00A C00M C00Q 179.9(2) . . . . ?
C00E C00G C00I C00F -0.2(4) . . . . ?
C00F C00K C00L C00E 1.1(4) . . . . ?
C00G C00E C00H F007 150.0(2) . . . . ?
C00G C00E C00H F008 30.6(3) . . . . ?
C00G C00E C00H C00B -89.9(3) . . . . ?
C00G C00E C00L C00K -0.4(4) . . . . ?
C00H C00B C00C F001 66.7(3) . . . . ?
C00H C00B C00C F006 -51.1(3) . . . . ?
C00H C00B C00C C00D -172.3(2) . . . . ?
C00H C00E C00G C00I 176.6(2) . . . . ?
C00H C00E C00L C00K -177.1(2) . . . . ?
C00I C00F C00K C00L -1.4(4) . . . . ?
C00J C00A C00D F004 -150.1(2) . . . . ?
C00J C00A C00D F005 -31.2(3) . . . . ?
C00J C00A C00D C00C 88.7(3) . . . . ?
C00J C00A C00M C00Q 2.4(4) . . . . ?
C00J C00O C00P C00Q 1.3(4) . . . . ?
C00K C00F C00I C00G 1.0(4) . . . . ?
C00L C00E C00G C00I -0.1(4) . . . . ?
C00L C00E C00H F007 -33.3(3) . . . . ?
C00L C00E C00H F008 -152.7(2) . . . . ?
C00L C00E C00H C00B 86.8(3) . . . . ?
C00M C00A C00D F004 32.4(3) . . . . ?
C00M C00A C00D F005 151.3(2) . . . . ?
C00M C00A C00D C00C -88.8(3) . . . . ?
C00M C00A C00J C00O -0.9(4) . . . . ?
C00N C00F C00I C00G -178.8(2) . . . . ?
C00N C00F C00K C00L 178.4(2) . . . . ?
C00O C00P C00Q C00M 0.2(5) . . . . ?

_olex2_exptl_crystal_mounting_method Loop
_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
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hot hexane'
