# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_ffensaiqin
_database_code_depnum_ccdc_archive 'CCDC 1984084'
_audit_update_record             
;
2020-02-14 deposited with the CCDC.	2020-05-18 downloaded from the CCDC.
;
_audit_creation_date             2019-12-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C25 H16 F N O S, 0.5(C2 Cl4)'
_chemical_formula_sum            'C26 H16 Cl2 F N O S'
_chemical_formula_weight         480.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O S N F'
_chemical_oxdiff_usercomment     'C H O S N F'
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'
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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   9.1731(2)
_cell_length_b                   11.0168(3)
_cell_length_c                   11.6865(4)
_cell_angle_alpha                115.261(3)
_cell_angle_beta                 101.427(2)
_cell_angle_gamma                92.737(2)
_cell_volume                     1035.18(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    16009
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.8170
_cell_measurement_theta_min      4.2630
_exptl_absorpt_coefficient_mu    4.013
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            34398
_diffrn_reflns_theta_full        67.07
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         4.31
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1975
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -117.00  -9.00   1.00    1.00    --  -41.12 -77.00-120.00  108
  2  ω   -117.00  -9.00   1.00    1.00    --  -41.12 -77.00 -60.00  108
  3  ω    -92.00  -2.00   1.00    1.00    --  -41.12 125.00  90.00   90
  4  ω    -69.00  32.00   1.00    1.00    --  -41.12  57.00   0.00  101
  5  ω   -117.00  -9.00   1.00    1.00    --  -41.12 -77.00-180.00  108
  6  ω    -92.00  -2.00   1.00    1.00    --  -41.12 125.00-180.00   90
  7  ω     13.00 114.00   1.00    1.00    --   41.12  57.00  60.00  101
  8  ω     23.00  97.00   1.00    1.00    --   41.12-125.00  90.00   74
  9  ω     13.00 114.00   1.00    1.00    --   41.12  57.00 -60.00  101
 10  ω     17.00 116.00   1.00    1.00    --   41.12  37.00  30.00   99
 11  ω      9.00 117.00   1.00    1.00    --   41.12  77.00  90.00  108
 12  ω      9.00 117.00   1.00    1.00    --   41.12  77.00 150.00  108
 13  ω     73.00 178.00   1.00    3.95    --  105.32  77.00 120.00  105
 14  ω     76.00 178.00   1.00    3.95    --  105.32  61.00 -30.00  102
 15  ω     29.00 138.00   1.00    3.95    --  105.32 -77.00 -30.00  109
 16  ω     76.00 178.00   1.00    3.95    --  105.32  61.00 120.00  102
 17  ω     76.00 178.00   1.00    3.95    --  105.32  61.00  30.00  102
 18  ω     76.00 178.00   1.00    3.95    --  105.32  61.00-150.00  102
 19  ω     73.00 178.00   1.00    3.95    --  105.32  77.00  60.00  105
 20  ω     23.00 109.00   1.00    3.95    --  105.32 -94.00-180.00   86
 21  ω     73.00 178.00   1.00    3.95    --  105.32  77.00 -90.00  105
 22  ω     73.00 178.00   1.00    3.95    --  105.32  77.00-120.00  105
 23  ω     76.00 178.00   1.00    3.95    --  105.32  61.00-120.00  102
 24  ω     76.00 178.00   1.00    3.95    --  105.32  61.00  90.00  102
 25  ω     73.00 178.00   1.00    3.95    --  105.32  77.00  30.00  105
 26  ω     73.00 178.00   1.00    3.95    --  105.32  77.00  90.00  105
 27  ω     76.00 178.00   1.00    3.95    --  105.32  61.00 150.00  102
 28  ω     73.00 178.00   1.00    3.95    --  105.32  77.00-180.00  105
 29  ω     73.00 178.00   1.00    3.95    --  105.32  77.00   0.00  105
 30  ω     73.00 178.00   1.00    3.95    --  105.32  77.00-150.00  105
 31  ω     76.00 178.00   1.00    3.95    --  105.32  61.00  60.00  102
 32  ω     76.00 178.00   1.00    3.95    --  105.32  61.00-180.00  102
 33  ω     76.00 178.00   1.00    3.95    --  105.32  61.00 -90.00  102
 34  ω     32.00 117.00   1.00    3.95    --  105.32-125.00 -30.00   85
 35  ω     32.00 117.00   1.00    3.95    --  105.32-125.00-180.00   85
 36  ω     73.00 178.00   1.00    3.95    --  105.32  77.00 -60.00  105
 37  ω     73.00 178.00   1.00    3.95    --  105.32  77.00 150.00  105
 38  ω     76.00 178.00   1.00    3.95    --  105.32  61.00 -60.00  102
 39  ω     76.00 178.00   1.00    3.95    --  105.32  61.00   0.00  102
 40  ω   -113.00 -13.00   1.00    1.00    --  -41.12 -57.00-180.00  100
 41  ω     17.00 116.00   1.00    1.00    --   41.12  37.00-150.00   99
 42  ω    -47.00 129.00   1.00    1.00    --   41.12   0.00 -90.00  176
 43  ω    -47.00 129.00   1.00    1.00    --   41.12   0.00-180.00  176
 44  ω    -47.00 129.00   1.00    1.00    --   41.12   0.00-150.00  176
 45  ω     17.00 116.00   1.00    1.00    --   41.12  37.00  90.00   99
 46  ω     17.00 116.00   1.00    1.00    --   41.12  37.00-120.00   99
 47  ω    -47.00 129.00   1.00    1.00    --   41.12   0.00 -60.00  176
 48  ω    -47.00 129.00   1.00    1.00    --   41.12   0.00 -30.00  176
 49  ω    -47.00 129.00   1.00    1.00    --   41.12   0.00   0.00  176
 50  ω    -47.00 129.00   1.00    1.00    --   41.12   0.00  30.00  176
 51  ω    -47.00 129.00   1.00    1.00    --   41.12   0.00  60.00  176
 52  ω    -47.00 129.00   1.00    1.00    --   41.12   0.00-120.00  176
 53  ω     33.00 105.00   1.00    3.95    --  105.32 -61.00-150.00   72
;
_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      -0.0685567000
_diffrn_orient_matrix_UB_12      0.0297314000
_diffrn_orient_matrix_UB_13      0.1177206000
_diffrn_orient_matrix_UB_21      -0.1590726000
_diffrn_orient_matrix_UB_22      -0.0337973000
_diffrn_orient_matrix_UB_23      -0.0895374000
_diffrn_orient_matrix_UB_31      -0.0047157000
_diffrn_orient_matrix_UB_32      -0.1497562000
_diffrn_orient_matrix_UB_33      -0.0263103000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3247
_reflns_number_total             3682
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.876
_refine_diff_density_min         -1.695
_refine_diff_density_rms         0.189
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.630
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3680
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1085
_refine_ls_R_factor_gt           0.1029
_refine_ls_restrained_S_all      1.630
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3289
_refine_ls_wR_factor_ref         0.3450
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17), C18(H18),
 C21(H21), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C29(H29), C30(H30)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.14775(10) 0.65463(16) 0.02951(11) 0.0793(6) Uani 1 d . . .
N1 N 0.2984(3) 0.7145(3) -0.1621(3) 0.0430(7) Uani 1 d . . .
O2 O 0.6546(3) 0.6361(3) 0.3285(3) 0.0633(8) Uani 1 d . . .
C3 C 0.1404(3) 0.6765(3) -0.1999(3) 0.0399(7) Uani 1 d . . .
C4 C 0.6974(4) 0.6934(3) 0.2697(3) 0.0453(8) Uani 1 d . . .
C5 C 0.3938(3) 0.7026(3) -0.0597(3) 0.0364(7) Uani 1 d . . .
C6 C 0.5946(4) 0.6951(3) 0.1549(3) 0.0412(7) Uani 1 d . . .
C7 C 0.3409(3) 0.6755(3) 0.0339(3) 0.0415(7) Uani 1 d . . .
C8 C 0.8552(4) 0.7622(3) 0.3108(3) 0.0446(8) Uani 1 d . . .
C9 C 0.4383(4) 0.6705(3) 0.1370(3) 0.0426(7) Uani 1 d . . .
H9 H 0.4000 0.6504 0.1959 0.051 Uiso 1 calc . . R
C10 C 0.6472(3) 0.7181(3) 0.0609(3) 0.0442(8) Uani 1 d . . .
H10 H 0.7503 0.7331 0.0697 0.053 Uiso 1 calc . . R
C11 C 0.3690(3) 0.7534(3) -0.2437(3) 0.0394(7) Uani 1 d . . .
C12 C 0.5498(3) 0.7191(3) -0.0451(3) 0.0421(7) Uani 1 d . . .
H12 H 0.5885 0.7310 -0.1080 0.051 Uiso 1 calc . . R
C13 C 0.9694(4) 0.7039(3) 0.3574(3) 0.0486(8) Uani 1 d . . .
H13 H 0.9453 0.6234 0.3621 0.058 Uiso 1 calc . . R
C14 C 0.3994(3) 0.6550(3) -0.3547(3) 0.0426(7) Uani 1 d . . .
H14 H 0.3700 0.5637 -0.3789 0.051 Uiso 1 calc . . R
C15 C 0.0627(4) 0.6419(3) -0.1239(3) 0.0453(8) Uani 1 d . . .
C16 C 0.8953(4) 0.8853(4) 0.3080(3) 0.0532(9) Uani 1 d . . .
H16 H 0.8208 0.9261 0.2774 0.064 Uiso 1 calc . . R
C17 C 0.4732(4) 0.6917(4) -0.4296(3) 0.0507(8) Uani 1 d . . .
H17 H 0.4942 0.6253 -0.5039 0.061 Uiso 1 calc . . R
C18 C 0.4101(4) 0.8887(4) -0.2089(4) 0.0541(9) Uani 1 d . . .
H18 H 0.3884 0.9553 -0.1350 0.065 Uiso 1 calc . . R
F20 F 1.2956(3) 0.9413(4) 0.4289(4) 0.1070(13) Uani 1 d . . .
C21 C 0.0576(4) 0.6748(4) -0.3140(3) 0.0503(8) Uani 1 d . . .
H21 H 0.1075 0.6974 -0.3657 0.060 Uiso 1 calc . . R
C23 C -0.0927(4) 0.6026(4) -0.1659(4) 0.0530(9) Uani 1 d . . .
H23 H -0.1431 0.5763 -0.1165 0.064 Uiso 1 calc . . R
C24 C 1.1176(4) 0.7639(4) 0.3967(4) 0.0595(10) Uani 1 d . . .
H24 H 1.1936 0.7243 0.4271 0.071 Uiso 1 calc . . R
C25 C -0.1727(4) 0.6020(4) -0.2788(4) 0.0628(10) Uani 1 d . . .
H25 H -0.2764 0.5761 -0.3054 0.075 Uiso 1 calc . . R
C26 C 1.0426(5) 0.9467(4) 0.3496(4) 0.0658(11) Uani 1 d . . .
H26 H 1.0683 1.0297 0.3502 0.079 Uiso 1 calc . . R
C27 C 0.5155(4) 0.8266(4) -0.3943(4) 0.0562(9) Uani 1 d . . .
H27 H 0.5656 0.8513 -0.4447 0.067 Uiso 1 calc . . R
C28 C 1.1504(5) 0.8823(5) 0.3899(4) 0.0652(11) Uani 1 d . . .
C29 C -0.0975(4) 0.6401(4) -0.3525(4) 0.0614(10) Uani 1 d . . .
H29 H -0.1509 0.6425 -0.4278 0.074 Uiso 1 calc . . R
C30 C 0.4842(5) 0.9249(4) -0.2850(4) 0.0628(10) Uani 1 d . . .
H30 H 0.5127 1.0161 -0.2617 0.075 Uiso 1 calc . . R
C1 C 0.1636(14) 1.0169(12) 0.0772(8) 0.106(3) Uani 1 d . . .
Cl1 Cl 0.1563(5) 1.0323(4) 0.0142(8) 0.235(3) Uani 1 d . . .
Cl2 Cl 0.004(4) 0.994(3) 0.070(2) 0.54(2) Uani 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C7 1.763(3) . ?
S1 C15 1.750(3) . ?
N1 C3 1.415(4) . ?
N1 C5 1.394(4) . ?
N1 C11 1.442(4) . ?
O2 C4 1.215(4) . ?
C3 C15 1.398(5) . ?
C3 C21 1.389(5) . ?
C4 C6 1.487(4) . ?
C4 C8 1.487(5) . ?
C5 C7 1.413(4) . ?
C5 C12 1.401(4) . ?
C6 C9 1.403(5) . ?
C6 C10 1.393(4) . ?
C7 C9 1.374(5) . ?
C8 C13 1.394(5) . ?
C8 C16 1.404(5) . ?
C10 C12 1.381(4) . ?
C11 C14 1.381(4) . ?
C11 C18 1.378(5) . ?
C13 C24 1.380(5) . ?
C14 C17 1.379(5) . ?
C15 C23 1.394(5) . ?
C16 C26 1.376(6) . ?
C17 C27 1.374(6) . ?
C18 C30 1.388(5) . ?
F20 C28 1.352(5) . ?
C21 C29 1.386(5) . ?
C23 C25 1.374(6) . ?
C24 C28 1.363(6) . ?
C25 C29 1.382(6) . ?
C26 C28 1.368(6) . ?
C27 C30 1.372(6) . ?
C1 Cl1 0.814(10) . ?
C1 Cl2 1.46(3) . ?
C1 Cl2 2.02(4) 2_575 ?
Cl1 Cl2 1.53(4) 2_575 ?
Cl1 Cl2 1.76(3) . ?
Cl2 C1 2.02(4) 2_575 ?
Cl2 Cl1 1.53(4) 2_575 ?
Cl2 Cl2 1.68(4) 2_575 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 S1 C7 102.53(15) . . ?
C3 N1 C11 118.1(2) . . ?
C5 N1 C3 124.7(3) . . ?
C5 N1 C11 116.7(2) . . ?
C15 C3 N1 121.7(3) . . ?
C21 C3 N1 120.2(3) . . ?
C21 C3 C15 118.1(3) . . ?
O2 C4 C6 121.1(3) . . ?
O2 C4 C8 120.3(3) . . ?
C8 C4 C6 118.6(3) . . ?
N1 C5 C7 123.0(3) . . ?
N1 C5 C12 120.2(3) . . ?
C12 C5 C7 116.9(3) . . ?
C9 C6 C4 120.0(3) . . ?
C10 C6 C4 122.5(3) . . ?
C10 C6 C9 117.5(3) . . ?
C5 C7 S1 122.0(2) . . ?
C9 C7 S1 116.5(2) . . ?
C9 C7 C5 121.5(3) . . ?
C13 C8 C4 118.8(3) . . ?
C13 C8 C16 118.0(3) . . ?
C16 C8 C4 123.2(3) . . ?
C7 C9 C6 121.2(3) . . ?
C12 C10 C6 121.5(3) . . ?
C14 C11 N1 120.0(3) . . ?
C18 C11 N1 120.0(3) . . ?
C18 C11 C14 120.0(3) . . ?
C10 C12 C5 121.3(3) . . ?
C24 C13 C8 120.9(3) . . ?
C17 C14 C11 120.2(3) . . ?
C3 C15 S1 123.7(2) . . ?
C23 C15 S1 116.3(3) . . ?
C23 C15 C3 119.9(3) . . ?
C26 C16 C8 121.2(3) . . ?
C27 C17 C14 119.9(3) . . ?
C11 C18 C30 119.5(3) . . ?
C29 C21 C3 121.6(3) . . ?
C25 C23 C15 121.1(3) . . ?
C28 C24 C13 118.7(4) . . ?
C23 C25 C29 119.4(3) . . ?
C28 C26 C16 118.2(4) . . ?
C30 C27 C17 120.2(3) . . ?
F20 C28 C24 118.6(4) . . ?
F20 C28 C26 118.4(4) . . ?
C24 C28 C26 123.0(4) . . ?
C25 C29 C21 119.9(3) . . ?
C27 C30 C18 120.2(3) . . ?
Cl1 C1 Cl2 43.3(9) . 2_575 ?
Cl1 C1 Cl2 97.6(14) . . ?
Cl2 C1 Cl2 54.9(12) . 2_575 ?
C1 Cl1 Cl2 55.1(13) . . ?
C1 Cl1 Cl2 115.4(12) . 2_575 ?
Cl2 Cl1 Cl2 60.8(14) 2_575 . ?
C1 Cl2 C1 125.1(12) . 2_575 ?
C1 Cl2 Cl1 146.0(15) . 2_575 ?
C1 Cl2 Cl1 27.3(6) . . ?
C1 Cl2 Cl2 80(2) . 2_575 ?
Cl1 Cl2 C1 21.4(6) 2_575 2_575 ?
Cl1 Cl2 C1 98.0(11) . 2_575 ?
Cl1 Cl2 Cl1 119.2(14) 2_575 . ?
Cl1 Cl2 Cl2 66(2) 2_575 2_575 ?
Cl2 Cl2 C1 45(2) 2_575 2_575 ?
Cl2 Cl2 Cl1 52.9(16) 2_575 . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.980
_oxdiff_exptl_absorpt_empirical_full_min 0.300
####################################################################### 
# 
# 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_ldffeneqin
_database_code_depnum_ccdc_archive 'CCDC 1984091'
_audit_update_record             
;
2020-02-14 deposited with the CCDC.	2020-05-18 downloaded from the CCDC.
;
_audit_creation_date             2019-12-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C25 H16 F N O2'
_chemical_formula_sum            'C25 H16 F N O2'
_chemical_formula_weight         381.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C25 H16 O2 N1 F1'
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'
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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   8.85361(17)
_cell_length_b                   9.38414(18)
_cell_length_c                   11.7086(2)
_cell_angle_alpha                99.9418(16)
_cell_angle_beta                 98.5741(16)
_cell_angle_gamma                94.0033(16)
_cell_volume                     942.91(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    19309
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.8540
_cell_measurement_theta_min      4.7850
_exptl_absorpt_coefficient_mu    0.750
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75296
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       bulk
_exptl_crystal_F_000             396
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0096
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            32193
_diffrn_reflns_theta_full        67.07
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         3.89
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1975
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -113.00 -13.00   1.00    3.87    --  -41.12 -57.00-180.00  100
  2  ω   -113.00 -13.00   1.00    3.87    --  -41.12 -57.00 -30.00  100
  3  ω    -65.00  33.00   1.00    3.87    --  -41.12  37.00 -30.00   98
  4  ω   -114.00 -12.00   1.00    3.87    --  -41.12 -62.00 132.00  102
  5  ω     23.00  97.00   1.00    3.87    --   41.12-125.00-180.00   74
  6  ω     23.00  97.00   1.00    3.87    --   41.12-125.00  90.00   74
  7  ω     17.00 116.00   1.00    3.87    --   41.12  37.00  90.00   99
  8  ω      8.00  45.00   1.00    3.87    --   42.00  82.00 -62.76   37
  9  ω     16.00  45.00   1.00    3.87    --   50.00  81.00-178.16   29
 10  ω     17.00  45.00   1.00    3.87    --   50.00  80.00  83.95   28
 11  ω     25.00 134.00   1.00    3.87    --   58.00  77.00-102.61  109
 12  ω     30.00 137.00   1.00    3.87    --   62.00  75.00  41.64  107
 13  ω     30.00 138.00   1.00    3.87    --   62.00  76.00-150.72  108
 14  ω     30.00 138.00   1.00    3.87    --   62.00  76.00   8.16  108
 15  ω     34.00 141.00   1.00    3.87    --   66.00  75.00 159.07  107
 16  ω     33.00 142.00   1.00    3.87    --   66.00  77.00 110.52  109
 17  ω     37.00 146.00   1.00    3.87    --   70.00  77.00 -55.77  109
 18  ω     37.00 146.00   1.00    3.87    --   70.00  77.00  75.42  109
 19  ω     37.00 146.00   1.00    3.87    --   70.00  77.00  47.46  109
 20  ω     73.00 178.00   1.00   15.48    --  105.32  77.00-150.00  105
 21  ω     23.00 109.00   1.00   15.48    --  105.32 -94.00-150.00   86
 22  ω     76.00 178.00   1.00   15.48    --  105.32  62.00 -89.00  102
 23  ω     73.00 178.00   1.00   15.48    --  105.32  77.00 120.00  105
 24  ω     73.00 178.00   1.00   15.48    --  105.32  77.00  90.00  105
 25  ω     73.00 178.00   1.00   15.48    --  105.32  77.00 150.00  105
 26  ω     76.00 178.00   1.00   15.48    --  105.32  61.00 -30.00  102
 27  ω     76.00 178.00   1.00   15.48    --  105.32  61.00-120.00  102
 28  ω     73.00 178.00   1.00   15.48    --  105.32  77.00 -60.00  105
 29  ω     73.00 178.00   1.00   15.48    --  105.32  77.00  60.00  105
 30  ω     32.00 117.00   1.00   15.48    --  105.32-125.00   0.00   85
 31  ω     76.00 178.00   1.00   15.48    --  105.32  61.00 -60.00  102
 32  ω     32.00 117.00   1.00   15.48    --  105.32-125.00-150.00   85
 33  ω     76.00 178.00   1.00   15.48    --  105.32  61.00-150.00  102
 34  ω     73.00 178.00   1.00   15.48    --  105.32  77.00 -30.00  105
 35  ω     76.00 178.00   1.00   15.48    --  105.32  61.00   0.00  102
 36  ω     73.00 178.00   1.00   15.48    --  105.32  77.00  30.00  105
 37  ω     73.00 178.00   1.00   15.48    --  105.32  77.00-180.00  105
 38  ω     76.00 178.00   1.00   15.48    --  105.32  61.00  30.00  102
 39  ω     32.00 131.00   1.00   15.48    --  105.32 -45.00-150.00   99
 40  ω     76.00 178.00   1.00   15.48    --  105.32  61.00 150.00  102
 41  ω     29.00 138.00   1.00   15.48    --  105.32 -77.00   0.00  109
 42  ω    -47.00 129.00   1.00    3.87    --   41.12   0.00 -90.00  176
 43  ω    -47.00 129.00   1.00    3.87    --   41.12   0.00-150.00  176
 44  ω    -47.00 129.00   1.00    3.87    --   41.12   0.00-180.00  176
 45  ω     23.00  97.00   1.00    3.87    --   41.12-125.00-150.00   74
 46  ω    -47.00 129.00   1.00    3.87    --   41.12   0.00 -60.00  176
 47  ω    -47.00 129.00   1.00    3.87    --   41.12   0.00-120.00  176
 48  ω    -47.00 115.00   1.00    3.87    --   41.12   0.00 -30.00  162
 49  ω     16.00  45.00   1.00    3.87    --   50.00  82.00   4.17   29
 50  ω     16.00  45.00   1.00    3.87    --   50.00  82.00-103.53   29
 51  ω     26.00 134.00   1.00    3.87    --   58.00  76.00 -45.05  108
 52  ω     26.00 134.00   1.00    3.87    --   58.00  76.00  96.43  108
 53  ω     25.00 134.00   1.00    3.87    --   58.00  77.00 -75.49  109
 54  ω     30.00 137.00   1.00    3.87    --   62.00  75.00 -12.77  107
 55  ω     30.00 138.00   1.00    3.87    --   62.00  76.00-178.31  108
 56  ω     30.00 138.00   1.00    3.87    --   62.00  76.00 146.62  108
;
_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      0.0218771000
_diffrn_orient_matrix_UB_12      0.1427005000
_diffrn_orient_matrix_UB_13      0.0908798000
_diffrn_orient_matrix_UB_21      -0.1587949000
_diffrn_orient_matrix_UB_22      -0.0361742000
_diffrn_orient_matrix_UB_23      0.0324491000
_diffrn_orient_matrix_UB_31      0.0746467000
_diffrn_orient_matrix_UB_32      -0.0798537000
_diffrn_orient_matrix_UB_33      0.0949997000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3061
_reflns_number_total             3362
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3362
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0472
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0683P)²+0.1229P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1174
_refine_ls_wR_factor_ref         0.1214
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C10(H10), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20),
 C21(H21), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.34683(11) 0.11548(13) 0.08222(8) 0.0712(3) Uani 1 d . . .
C2 C 0.20176(14) 0.16134(13) 0.08349(11) 0.0507(3) Uani 1 d . . .
C3 C 0.15092(14) 0.21264(13) 0.18994(10) 0.0491(3) Uani 1 d . . .
C4 C 0.11272(14) 0.15937(13) -0.02244(11) 0.0516(3) Uani 1 d . . .
H4 H 0.1496 0.1251 -0.0914 0.062 Uiso 1 calc . . R
N5 N 0.24873(12) 0.22088(13) 0.29526(9) 0.0580(3) Uani 1 d . . .
C6 C -0.08725(14) 0.25374(14) 0.07616(11) 0.0528(3) Uani 1 d . . .
H6 H -0.1856 0.2833 0.0741 0.063 Uiso 1 calc . . R
O7 O -0.09845(12) 0.12353(11) -0.23301(8) 0.0707(3) Uani 1 d . . .
C8 C 0.39427(14) 0.17014(14) 0.29580(11) 0.0533(3) Uani 1 d . . .
C9 C -0.12636(15) 0.20396(14) -0.14594(11) 0.0531(3) Uani 1 d . . .
C10 C 0.00340(14) 0.25548(14) 0.18324(11) 0.0531(3) Uani 1 d . . .
H10 H -0.0351 0.2859 0.2521 0.064 Uiso 1 calc . . R
C11 C 0.44093(15) 0.11942(15) 0.18863(12) 0.0561(3) Uani 1 d . . .
C12 C -0.03348(14) 0.20835(13) -0.02874(10) 0.0494(3) Uani 1 d . . .
C13 C 0.19934(14) 0.27654(14) 0.40459(10) 0.0518(3) Uani 1 d . . .
F14 F -0.62783(12) 0.53328(13) -0.18678(10) 0.1044(4) Uani 1 d . . .
C15 C -0.25612(15) 0.29653(13) -0.15779(10) 0.0521(3) Uani 1 d . . .
C16 C 0.63716(17) 0.1170(2) 0.39358(15) 0.0760(4) Uani 1 d . . .
H16 H 0.7031 0.1155 0.4630 0.091 Uiso 1 calc . . R
C17 C -0.37769(17) 0.51395(15) -0.10036(13) 0.0635(4) Uani 1 d . . .
H17 H -0.3754 0.6056 -0.0544 0.076 Uiso 1 calc . . R
C18 C 0.58331(16) 0.07057(17) 0.18434(14) 0.0676(4) Uani 1 d . . .
H18 H 0.6132 0.0384 0.1122 0.081 Uiso 1 calc . . R
C19 C -0.38587(17) 0.24389(16) -0.24093(12) 0.0655(4) Uani 1 d . . .
H19 H -0.3882 0.1540 -0.2896 0.079 Uiso 1 calc . . R
C20 C 0.49407(16) 0.16759(17) 0.39802(13) 0.0656(4) Uani 1 d . . .
H20 H 0.4651 0.2000 0.4705 0.079 Uiso 1 calc . . R
C21 C -0.51108(19) 0.32280(19) -0.25233(14) 0.0792(5) Uani 1 d . . .
H21 H -0.5982 0.2869 -0.3075 0.095 Uiso 1 calc . . R
C22 C -0.50383(18) 0.45587(17) -0.18011(13) 0.0707(4) Uani 1 d . . .
C23 C 0.11565(16) 0.18553(16) 0.45663(12) 0.0637(4) Uani 1 d . . .
H23 H 0.0921 0.0880 0.4221 0.076 Uiso 1 calc . . R
C24 C -0.25278(16) 0.43399(14) -0.08897(12) 0.0581(3) Uani 1 d . . .
H24 H -0.1655 0.4723 -0.0348 0.070 Uiso 1 calc . . R
C25 C 0.18638(19) 0.47363(17) 0.56046(13) 0.0720(4) Uani 1 d . . .
H25 H 0.2105 0.5708 0.5958 0.086 Uiso 1 calc . . R
C26 C 0.23604(16) 0.42086(15) 0.45540(12) 0.0624(3) Uani 1 d . . .
H26 H 0.2933 0.4822 0.4199 0.075 Uiso 1 calc . . R
C27 C 0.06631(17) 0.23977(19) 0.56097(12) 0.0717(4) Uani 1 d . . .
H27 H 0.0087 0.1788 0.5965 0.086 Uiso 1 calc . . R
C28 C 0.10229(17) 0.38304(19) 0.61180(12) 0.0703(4) Uani 1 d . . .
H28 H 0.0691 0.4190 0.6820 0.084 Uiso 1 calc . . R
C29 C 0.68179(17) 0.06936(19) 0.28725(15) 0.0758(4) Uani 1 d . . .
H29 H 0.7781 0.0363 0.2846 0.091 Uiso 1 calc . . R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.3841(15) . ?
O1 C11 1.3849(16) . ?
C2 C3 1.4065(16) . ?
C2 C4 1.3633(18) . ?
C3 N5 1.3841(16) . ?
C3 C10 1.3883(17) . ?
C4 C12 1.3995(17) . ?
N5 C8 1.4041(16) . ?
N5 C13 1.4390(15) . ?
C6 C10 1.3810(18) . ?
C6 C12 1.3924(16) . ?
O7 C9 1.2271(15) . ?
C8 C11 1.3956(18) . ?
C8 C20 1.3826(19) . ?
C9 C12 1.4833(18) . ?
C9 C15 1.4924(18) . ?
C11 C18 1.3759(18) . ?
C13 C23 1.370(2) . ?
C13 C26 1.3770(19) . ?
F14 C22 1.3581(17) . ?
C15 C19 1.3901(19) . ?
C15 C24 1.3938(18) . ?
C16 C20 1.388(2) . ?
C16 C29 1.373(2) . ?
C17 C22 1.358(2) . ?
C17 C24 1.382(2) . ?
C18 C29 1.380(2) . ?
C19 C21 1.378(2) . ?
C21 C22 1.373(2) . ?
C23 C27 1.3850(19) . ?
C25 C26 1.390(2) . ?
C25 C28 1.364(2) . ?
C27 C28 1.368(2) . ?

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
C2 O1 C11 118.46(10) . . ?
O1 C2 C3 121.12(11) . . ?
C4 C2 O1 117.27(10) . . ?
C4 C2 C3 121.57(11) . . ?
N5 C3 C2 119.57(11) . . ?
N5 C3 C10 123.06(11) . . ?
C10 C3 C2 117.36(11) . . ?
C2 C4 C12 120.81(11) . . ?
C3 N5 C8 120.01(10) . . ?
C3 N5 C13 120.07(10) . . ?
C8 N5 C13 119.88(10) . . ?
C10 C6 C12 120.91(11) . . ?
C11 C8 N5 118.86(12) . . ?
C20 C8 N5 122.98(12) . . ?
C20 C8 C11 118.16(12) . . ?
O7 C9 C12 120.50(12) . . ?
O7 C9 C15 119.74(11) . . ?
C12 C9 C15 119.76(10) . . ?
C6 C10 C3 121.24(11) . . ?
O1 C11 C8 121.87(11) . . ?
C18 C11 O1 117.01(12) . . ?
C18 C11 C8 121.12(13) . . ?
C4 C12 C9 118.92(10) . . ?
C6 C12 C4 118.00(11) . . ?
C6 C12 C9 123.02(11) . . ?
C23 C13 N5 119.61(12) . . ?
C23 C13 C26 120.74(12) . . ?
C26 C13 N5 119.65(12) . . ?
C19 C15 C9 118.80(12) . . ?
C19 C15 C24 118.46(12) . . ?
C24 C15 C9 122.74(11) . . ?
C29 C16 C20 120.33(14) . . ?
C22 C17 C24 118.62(13) . . ?
C11 C18 C29 119.95(14) . . ?
C21 C19 C15 121.05(13) . . ?
C8 C20 C16 120.64(14) . . ?
C22 C21 C19 118.23(14) . . ?
F14 C22 C17 117.85(14) . . ?
F14 C22 C21 119.30(14) . . ?
C17 C22 C21 122.84(14) . . ?
C13 C23 C27 119.53(14) . . ?
C17 C24 C15 120.73(12) . . ?
C28 C25 C26 120.08(14) . . ?
C13 C26 C25 119.09(14) . . ?
C28 C27 C23 119.99(15) . . ?
C25 C28 C27 120.56(13) . . ?
C16 C29 C18 119.79(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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.261
_oxdiff_exptl_absorpt_empirical_full_min 0.868
####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1984092'
_audit_update_record             
;
2020-05-08 deposited with the CCDC.	2020-05-18 downloaded from the CCDC.
;
_audit_creation_date             2020-05-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H18 F N O'
_chemical_formula_sum            'C25 H18 F N O'
_chemical_formula_weight         367.40
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   20.990(4)
_cell_length_b                   9.1680(16)
_cell_length_c                   10.0159(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1927.4(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4962
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.08
_cell_measurement_theta_min      2.42
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            19763
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.044
_diffrn_reflns_theta_min         1.940
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.821
_reflns_Friedel_fraction_full    0.968
_reflns_Friedel_fraction_max     0.900
_reflns_number_gt                4233
_reflns_number_total             5837
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 
;
 Flack x determined using 1512 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(4)
_refine_ls_extinction_coef       0.0182(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         5837
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0413
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0389P)²+0.1638P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.1023
_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:
 C1(H1), C2(H2), C4(H4), C5(H5), C9(H9), C10(H10), C12(H12), C13(H13),
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C21(H21), C22(H22), C23(H23),
  C24(H24), C25(H25)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.75320(8) -0.40520(17) 1.1097(2) 0.0915(6) Uani 1 1 d . . . . .
O1 O 0.68580(9) 0.25090(19) 1.17344(17) 0.0663(5) Uani 1 1 d . . . . .
N1 N 0.57603(8) 0.44664(17) 0.60706(17) 0.0452(4) Uani 1 1 d . . . . .
C1 C 0.73119(10) -0.0472(3) 0.9701(2) 0.0499(5) Uani 1 1 d . . . . .
H1 H 0.7400 0.0035 0.8918 0.060 Uiso 1 1 calc R . . . .
C2 C 0.74966(12) -0.1914(3) 0.9823(3) 0.0604(6) Uani 1 1 d . . . . .
H2 H 0.7711 -0.2383 0.9133 0.072 Uiso 1 1 calc R . . . .
C3 C 0.73575(12) -0.2625(3) 1.0971(3) 0.0610(6) Uani 1 1 d . . . . .
C4 C 0.70510(14) -0.1991(3) 1.2017(3) 0.0689(7) Uani 1 1 d . . . . .
H4 H 0.6963 -0.2516 1.2790 0.083 Uiso 1 1 calc R . . . .
C5 C 0.68754(12) -0.0552(3) 1.1900(2) 0.0573(6) Uani 1 1 d . . . . .
H5 H 0.6673 -0.0093 1.2610 0.069 Uiso 1 1 calc R . . . .
C6 C 0.69952(9) 0.0225(2) 1.0739(2) 0.0428(4) Uani 1 1 d . . . . .
C7 C 0.68021(9) 0.1791(2) 1.0714(2) 0.0441(4) Uani 1 1 d . . . . .
C8 C 0.65305(10) 0.2448(2) 0.9493(2) 0.0414(4) Uani 1 1 d . . . . .
C9 C 0.64329(10) 0.3954(2) 0.9450(2) 0.0462(5) Uani 1 1 d . . . . .
H9 H 0.6544 0.4517 1.0187 0.055 Uiso 1 1 calc R . . . .
C10 C 0.61772(11) 0.4626(2) 0.8351(2) 0.0461(5) Uani 1 1 d . . . . .
H10 H 0.6114 0.5630 0.8359 0.055 Uiso 1 1 calc R . . . .
C11 C 0.60109(9) 0.3821(2) 0.7219(2) 0.0408(4) Uani 1 1 d . . . . .
C12 C 0.60882(10) 0.2306(2) 0.7273(2) 0.0451(5) Uani 1 1 d . . . . .
H12 H 0.5967 0.1738 0.6547 0.054 Uiso 1 1 calc R . . . .
C13 C 0.63412(10) 0.1645(2) 0.8386(2) 0.0428(5) Uani 1 1 d . . . . .
H13 H 0.6387 0.0636 0.8398 0.051 Uiso 1 1 calc R . . . .
C14 C 0.58590(9) 0.5950(2) 0.5718(2) 0.0410(4) Uani 1 1 d . . . . .
C15 C 0.64203(10) 0.6677(2) 0.6032(2) 0.0499(5) Uani 1 1 d . . . . .
H15 H 0.6745 0.6190 0.6478 0.060 Uiso 1 1 calc R . . . .
C16 C 0.64944(12) 0.8127(3) 0.5677(3) 0.0610(6) Uani 1 1 d . . . . .
H16 H 0.6867 0.8615 0.5904 0.073 Uiso 1 1 calc R . . . .
C17 C 0.60222(14) 0.8853(2) 0.4993(3) 0.0640(7) Uani 1 1 d . . . . .
H17 H 0.6073 0.9831 0.4769 0.077 Uiso 1 1 calc R . . . .
C18 C 0.54783(14) 0.8129(3) 0.4645(3) 0.0620(7) Uani 1 1 d . . . . .
H18 H 0.5163 0.8612 0.4165 0.074 Uiso 1 1 calc R . . . .
C19 C 0.53913(11) 0.6682(2) 0.5002(2) 0.0518(5) Uani 1 1 d . . . . .
H19 H 0.5019 0.6199 0.4761 0.062 Uiso 1 1 calc R . . . .
C20 C 0.54152(9) 0.3560(2) 0.5153(2) 0.0431(4) Uani 1 1 d . . . . .
C21 C 0.56556(11) 0.3326(3) 0.3889(2) 0.0527(5) Uani 1 1 d . . . . .
H21 H 0.6032 0.3774 0.3624 0.063 Uiso 1 1 calc R . . . .
C22 C 0.53297(13) 0.2415(3) 0.3016(3) 0.0605(6) Uani 1 1 d . . . . .
H22 H 0.5488 0.2260 0.2161 0.073 Uiso 1 1 calc R . . . .
C23 C 0.47794(13) 0.1747(3) 0.3402(3) 0.0627(7) Uani 1 1 d . . . . .
H23 H 0.4564 0.1137 0.2814 0.075 Uiso 1 1 calc R . . . .
C24 C 0.45446(12) 0.1980(3) 0.4661(3) 0.0636(7) Uani 1 1 d . . . . .
H24 H 0.4172 0.1516 0.4927 0.076 Uiso 1 1 calc R . . . .
C25 C 0.48551(11) 0.2892(2) 0.5536(3) 0.0539(5) Uani 1 1 d . . . . .
H25 H 0.4688 0.3059 0.6382 0.065 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C3 1.364(3) . ?
O1 C7 1.221(3) . ?
N1 C11 1.397(3) . ?
N1 C14 1.421(2) . ?
N1 C20 1.436(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.383(3) . ?
C1 C6 1.390(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.354(4) . ?
C3 C4 1.360(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.387(3) . ?
C6 C7 1.492(3) . ?
C7 C8 1.478(3) . ?
C8 C9 1.396(3) . ?
C8 C13 1.389(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.371(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.397(3) . ?
C11 C12 1.399(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.375(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.389(3) . ?
C14 C19 1.389(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.385(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.377(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.366(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.387(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.379(3) . ?
C20 C25 1.380(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.389(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.363(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.370(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.376(3) . ?
C25 H25 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
C11 N1 C14 123.75(16) . . ?
C11 N1 C20 118.17(15) . . ?
C14 N1 C20 117.97(16) . . ?
C2 C1 H1 119.8 . . ?
C2 C1 C6 120.5(2) . . ?
C6 C1 H1 119.8 . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.4(2) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 F1 118.9(3) . . ?
C2 C3 C4 123.4(2) . . ?
C4 C3 F1 117.7(2) . . ?
C3 C4 H4 121.0 . . ?
C3 C4 C5 118.1(2) . . ?
C5 C4 H4 121.0 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.1(2) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C7 124.07(19) . . ?
C5 C6 C1 118.5(2) . . ?
C5 C6 C7 117.3(2) . . ?
O1 C7 C6 118.6(2) . . ?
O1 C7 C8 120.67(19) . . ?
C8 C7 C6 120.71(18) . . ?
C9 C8 C7 119.03(18) . . ?
C13 C8 C7 123.70(17) . . ?
C13 C8 C9 117.23(19) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 C8 121.76(19) . . ?
C10 C9 H9 119.1 . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.81(17) . . ?
C11 C10 H10 119.6 . . ?
N1 C11 C10 122.58(17) . . ?
N1 C11 C12 119.76(17) . . ?
C10 C11 C12 117.65(18) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.86(18) . . ?
C13 C12 H12 119.6 . . ?
C8 C13 H13 119.2 . . ?
C12 C13 C8 121.62(18) . . ?
C12 C13 H13 119.2 . . ?
C15 C14 N1 121.78(18) . . ?
C19 C14 N1 119.18(18) . . ?
C19 C14 C15 118.99(18) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.8(2) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.7(2) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.6(2) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 119.7 . . ?
C17 C18 C19 120.7(2) . . ?
C19 C18 H18 119.7 . . ?
C14 C19 H19 119.9 . . ?
C18 C19 C14 120.1(2) . . ?
C18 C19 H19 119.9 . . ?
C21 C20 N1 119.55(19) . . ?
C21 C20 C25 119.9(2) . . ?
C25 C20 N1 120.6(2) . . ?
C20 C21 H21 120.3 . . ?
C20 C21 C22 119.4(2) . . ?
C22 C21 H21 120.3 . . ?
C21 C22 H22 119.7 . . ?
C23 C22 C21 120.6(3) . . ?
C23 C22 H22 119.7 . . ?
C22 C23 H23 120.1 . . ?
C22 C23 C24 119.7(2) . . ?
C24 C23 H23 120.1 . . ?
C23 C24 H24 119.7 . . ?
C23 C24 C25 120.7(2) . . ?
C25 C24 H24 119.7 . . ?
C20 C25 H25 120.1 . . ?
C24 C25 C20 119.7(2) . . ?
C24 C25 H25 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C3 C4 C5 179.8(2) . . . . ?
O1 C7 C8 C9 10.2(3) . . . . ?
O1 C7 C8 C13 -167.3(2) . . . . ?
N1 C11 C12 C13 179.20(19) . . . . ?
N1 C14 C15 C16 -179.5(2) . . . . ?
N1 C14 C19 C18 -179.9(2) . . . . ?
N1 C20 C21 C22 178.2(2) . . . . ?
N1 C20 C25 C24 -177.4(2) . . . . ?
C1 C2 C3 F1 179.4(2) . . . . ?
C1 C2 C3 C4 -0.7(4) . . . . ?
C1 C6 C7 O1 -140.3(2) . . . . ?
C1 C6 C7 C8 41.5(3) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
C2 C1 C6 C7 177.4(2) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
C3 C4 C5 C6 1.3(4) . . . . ?
C4 C5 C6 C1 -1.5(3) . . . . ?
C4 C5 C6 C7 -178.5(2) . . . . ?
C5 C6 C7 O1 36.5(3) . . . . ?
C5 C6 C7 C8 -141.7(2) . . . . ?
C6 C1 C2 C3 0.4(3) . . . . ?
C6 C7 C8 C9 -171.73(19) . . . . ?
C6 C7 C8 C13 10.8(3) . . . . ?
C7 C8 C9 C10 -179.4(2) . . . . ?
C7 C8 C13 C12 179.7(2) . . . . ?
C8 C9 C10 C11 -0.8(3) . . . . ?
C9 C8 C13 C12 2.2(3) . . . . ?
C9 C10 C11 N1 -178.80(19) . . . . ?
C9 C10 C11 C12 2.8(3) . . . . ?
C10 C11 C12 C13 -2.3(3) . . . . ?
C11 N1 C14 C15 32.7(3) . . . . ?
C11 N1 C14 C19 -149.5(2) . . . . ?
C11 N1 C20 C21 -114.6(2) . . . . ?
C11 N1 C20 C25 63.7(3) . . . . ?
C11 C12 C13 C8 -0.2(3) . . . . ?
C13 C8 C9 C10 -1.7(3) . . . . ?
C14 N1 C11 C10 24.0(3) . . . . ?
C14 N1 C11 C12 -157.6(2) . . . . ?
C14 N1 C20 C21 61.7(3) . . . . ?
C14 N1 C20 C25 -119.9(2) . . . . ?
C14 C15 C16 C17 -1.3(4) . . . . ?
C15 C14 C19 C18 -2.0(3) . . . . ?
C15 C16 C17 C18 -0.8(4) . . . . ?
C16 C17 C18 C19 1.5(4) . . . . ?
C17 C18 C19 C14 -0.1(4) . . . . ?
C19 C14 C15 C16 2.7(3) . . . . ?
C20 N1 C11 C10 -159.9(2) . . . . ?
C20 N1 C11 C12 18.5(3) . . . . ?
C20 N1 C14 C15 -143.4(2) . . . . ?
C20 N1 C14 C19 34.3(3) . . . . ?
C20 C21 C22 C23 -0.5(3) . . . . ?
C21 C20 C25 C24 1.0(3) . . . . ?
C21 C22 C23 C24 0.2(4) . . . . ?
C22 C23 C24 C25 0.7(4) . . . . ?
C23 C24 C25 C20 -1.2(4) . . . . ?
C25 C20 C21 C22 -0.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
