# Electronic Supplementary Material (ESI) for ChemComm.
# 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_14
_database_code_depnum_ccdc_archive 'CCDC 1981921'
_audit_update_record             
;
2020-07-28 deposited with the CCDC.	2020-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H9 N O F4'
_chemical_formula_sum            'C16 H9 F4 N O'
_chemical_formula_weight         307.24
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_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.
;
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                   26.225(5)
_cell_length_b                   5.0080(10)
_cell_length_c                   10.261(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.42(3)
_cell_angle_gamma                90
_cell_volume                     1345.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    1228
_cell_measurement_theta_min      1.556
_cell_measurement_theta_max      29.125
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   0.349
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.710753083229
_diffrn_radiation_type           synchrotron
_diffrn_source                   synchrotron
_diffrn_measurement_device_type  'Dectris Eiger X 16M'
_diffrn_measurement_method       'Omega Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1228
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_theta_min         1.556
_diffrn_reflns_theta_max         29.125
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.254
_diffrn_measured_fraction_theta_full 0.269
_diffrn_reflns_Laue_measured_fraction_max 0.254
_diffrn_reflns_Laue_measured_fraction_full 0.269
_diffrn_reflns_point_group_measured_fraction_max 0.254
_diffrn_reflns_point_group_measured_fraction_full 0.269
_reflns_number_total             919
_reflns_number_gt                769
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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.
;
_computing_data_collection       'AS QEGUI'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'known structure'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1214P)²+2.2576P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         919
_refine_ls_number_parameters     29
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1126
_refine_ls_R_factor_gt           0.1026
_refine_ls_wR_factor_ref         0.2790
_refine_ls_wR_factor_gt          0.2677
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_restrained_S_all      1.157
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
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
C1 C 0.19044(5) 0.5127(3) 0.1697(2) 0.0263(11) Uiso 1 1 d G . . . .
F4 F 0.34898(5) 0.8864(4) 0.6404(2) 0.0376(9) Uiso 1 1 d G . . . .
C10 C 0.35082(4) 0.6832(3) 0.5554(2) 0.0285(12) Uiso 1 1 d G . . . .
C9 C 0.30746(4) 0.6252(2) 0.4769(2) 0.0269(11) Uiso 1 1 d G . . . .
C11 C 0.39600(4) 0.5407(3) 0.5483(2) 0.0287(11) Uiso 1 1 d G . . . .
C12 C 0.39772(4) 0.3307(3) 0.4601(2) 0.0289(12) Uiso 1 1 d G . . . .
C14 C 0.44266(4) 0.6166(3) 0.6348(2) 0.0320(12) Uiso 1 1 d G . . . .
C8 C 0.30952(4) 0.4124(2) 0.3894(2) 0.0244(11) Uiso 1 1 d G . . . .
H9 H 0.277116 0.727258 0.482517 0.029 Uiso 1 1 d G U . . .
C13 C 0.35433(4) 0.2649(3) 0.3822(2) 0.0275(11) Uiso 1 1 d G . . . .
H12 H 0.428425 0.232343 0.453153 0.033 Uiso 1 1 d G U . . .
F1 F 0.43208(5) 0.6384(4) 0.7601(2) 0.0453(11) Uiso 1 1 d G . . . .
F3 F 0.46237(5) 0.8497(3) 0.5993(2) 0.0378(9) Uiso 1 1 d G . . . .
F2 F 0.47980(4) 0.4343(3) 0.6284(3) 0.0415(10) Uiso 1 1 d G . . . .
C7 C 0.26468(4) 0.3349(2) 0.2995(2) 0.0259(10) Uiso 1 1 d G . . . .
H13 H 0.355238 0.118229 0.323553 0.031 Uiso 1 1 d G U . . .
O1 O 0.25696(6) 0.1005(3) 0.2696(3) 0.0313(9) Uiso 1 1 d G . . . .
N1 N 0.23506(4) 0.5400(3) 0.2546(2) 0.0259(10) Uiso 1 1 d G . . . .
H1 H 0.244030 0.702313 0.279671 0.031 Uiso 1 1 d G U . . .
C2 C 0.14959(5) 0.6815(3) 0.1904(2) 0.0288(12) Uiso 1 1 d G . . . .
C6 C 0.18752(6) 0.3296(4) 0.0670(2) 0.0320(12) Uiso 1 1 d G . . . .
H2 H 0.152086 0.808185 0.259451 0.038 Uiso 1 1 d G U . . .
C3 C 0.10474(6) 0.6647(4) 0.1093(3) 0.0309(12) Uiso 1 1 d G . . . .
H6 H 0.215613 0.215831 0.052315 0.037 Uiso 1 1 d G U . . .
C5 C 0.14302(7) 0.3152(4) -0.0136(2) 0.0400(15) Uiso 1 1 d G . . . .
C4 C 0.10174(6) 0.4802(4) 0.0070(3) 0.0355(13) Uiso 1 1 d G . . . .
C15 C 0.06215(6) 0.8332(4) 0.1335(3) 0.0361(13) Uiso 1 1 d G . . . .
H5 H 0.140854 0.190848 -0.083677 0.043 Uiso 1 1 d G U . . .
H4 H 0.071490 0.467669 -0.048456 0.043 Uiso 1 1 d G U . . .
C16 C 0.02681(6) 0.9745(5) 0.1538(3) 0.0472(17) Uiso 1 1 d G . . . .
H16 H -0.001308 1.086951 0.170037 0.057 Uiso 1 1 d G 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
C1 C2 1.3907 . ?
C1 C6 1.3954 . ?
C1 N1 1.4234 . ?
F4 C10 1.3429 . ?
C10 C9 1.3846 . ?
C10 C11 1.3890 . ?
C9 C8 1.3968 . ?
C9 H9 0.9504 . ?
C11 C12 1.3894 . ?
C11 C14 1.5167 . ?
C12 C13 1.3911 . ?
C12 H12 0.9502 . ?
C14 F1 1.3359 . ?
C14 F3 1.3360 . ?
C14 F2 1.3397 . ?
C8 C13 1.3939 . ?
C8 C7 1.5012 . ?
C13 H13 0.9506 . ?
C7 O1 1.2272 . ?
C7 N1 1.3522 . ?
N1 H1 0.8803 . ?
C2 C3 1.4021 . ?
C2 H2 0.9505 . ?
C6 C5 1.3915 . ?
C6 H6 0.9503 . ?
C3 C4 1.3974 . ?
C3 C15 1.4334 . ?
C5 C4 1.3877 . ?
C5 H5 0.9505 . ?
C4 H4 0.9503 . ?
C15 C16 1.1941 . ?
C16 H16 0.9504 . ?
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 C1 C6 120.5 . . ?
C2 C1 N1 117.4 . . ?
C6 C1 N1 122.1 . . ?
F4 C10 C9 118.5 . . ?
F4 C10 C11 119.2 . . ?
C9 C10 C11 122.3 . . ?
C10 C9 C8 118.2 . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
C10 C11 C12 119.0 . . ?
C10 C11 C14 120.1 . . ?
C12 C11 C14 121.0 . . ?
C11 C12 C13 119.8 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
F1 C14 F3 107.3 . . ?
F1 C14 F2 107.2 . . ?
F3 C14 F2 106.7 . . ?
F1 C14 C11 112.2 . . ?
F3 C14 C11 111.8 . . ?
F2 C14 C11 111.3 . . ?
C13 C8 C9 120.2 . . ?
C13 C8 C7 117.5 . . ?
C9 C8 C7 122.2 . . ?
C12 C13 C8 120.5 . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.7 . . ?
O1 C7 N1 123.9 . . ?
O1 C7 C8 120.8 . . ?
N1 C7 C8 115.2 . . ?
C7 N1 C1 124.8 . . ?
C7 N1 H1 117.6 . . ?
C1 N1 H1 117.6 . . ?
C1 C2 C3 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C5 C6 C1 119.3 . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
C4 C3 C2 119.5 . . ?
C4 C3 C15 120.7 . . ?
C2 C3 C15 119.8 . . ?
C4 C5 C6 120.9 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C4 C3 119.9 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.1 . . ?
C16 C15 C3 179.7 . . ?
C15 C16 H16 180.0 . . ?
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.055
_exptl_absorp_correction_type    none
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_source         'MX2 Beamline Australian Synchrotron'
####################################################################### 
# 
# 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_15
_database_code_depnum_ccdc_archive 'CCDC 1981922'
_audit_update_record             
;
2020-07-28 deposited with the CCDC.	2020-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H9 N O F4'
_chemical_formula_sum            'C16 H9 F4 N O'
_chemical_formula_weight         307.24
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_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.
;
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                   26.224(5)
_cell_length_b                   5.0080(10)
_cell_length_c                   10.260(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.41(3)
_cell_angle_gamma                90
_cell_volume                     1345.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    1230
_cell_measurement_theta_min      1.556
_cell_measurement_theta_max      29.129
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   0.349
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.710753083229
_diffrn_radiation_type           synchrotron
_diffrn_source                   synchrotron
_diffrn_measurement_device_type  'Dectris Eiger X 16M'
_diffrn_measurement_method       'Omega Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1230
_diffrn_reflns_av_unetI/netI     0.0889
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_theta_min         1.556
_diffrn_reflns_theta_max         29.129
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.254
_diffrn_measured_fraction_theta_full 0.269
_diffrn_reflns_Laue_measured_fraction_max 0.254
_diffrn_reflns_Laue_measured_fraction_full 0.269
_diffrn_reflns_point_group_measured_fraction_max 0.254
_diffrn_reflns_point_group_measured_fraction_full 0.269
_reflns_number_total             919
_reflns_number_gt                797
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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.
;
_computing_data_collection       'AS QEGUI'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'known structure'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1195P)²+2.4884P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         919
_refine_ls_number_parameters     29
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1166
_refine_ls_R_factor_gt           0.1089
_refine_ls_wR_factor_ref         0.2900
_refine_ls_wR_factor_gt          0.2819
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_restrained_S_all      1.134
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
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
C1 C 0.19047(5) 0.5128(3) 0.1696(2) 0.0275(11) Uiso 1 1 d G . . . .
F4 F 0.34898(5) 0.8862(4) 0.6405(2) 0.0380(9) Uiso 1 1 d G . . . .
C10 C 0.35083(4) 0.6831(3) 0.5555(2) 0.0294(12) Uiso 1 1 d G . . . .
C9 C 0.30747(4) 0.6251(2) 0.4770(2) 0.0277(11) Uiso 1 1 d G . . . .
C11 C 0.39601(4) 0.5406(3) 0.5483(2) 0.0292(12) Uiso 1 1 d G . . . .
C12 C 0.39774(4) 0.3307(3) 0.4602(2) 0.0300(12) Uiso 1 1 d G . . . .
C14 C 0.44266(4) 0.6165(3) 0.6349(2) 0.0335(13) Uiso 1 1 d G . . . .
C8 C 0.30954(4) 0.4124(2) 0.3894(2) 0.0247(11) Uiso 1 1 d G . . . .
H9 H 0.277125 0.727137 0.482573 0.030 Uiso 1 1 d G U . . .
C13 C 0.35435(5) 0.2649(3) 0.3822(2) 0.0272(11) Uiso 1 1 d G . . . .
H12 H 0.428447 0.232341 0.453194 0.033 Uiso 1 1 d G U . . .
F1 F 0.43208(5) 0.6383(4) 0.7602(2) 0.0447(11) Uiso 1 1 d G . . . .
F3 F 0.46237(5) 0.8496(3) 0.5994(3) 0.0384(9) Uiso 1 1 d G . . . .
F2 F 0.47981(4) 0.4342(4) 0.6285(3) 0.0416(10) Uiso 1 1 d G . . . .
C7 C 0.26471(4) 0.3349(2) 0.2995(2) 0.0261(11) Uiso 1 1 d G . . . .
H13 H 0.355269 0.118258 0.323552 0.031 Uiso 1 1 d G U . . .
O1 O 0.25699(6) 0.1005(3) 0.2696(3) 0.0319(10) Uiso 1 1 d G . . . .
N1 N 0.23509(4) 0.5400(3) 0.2546(2) 0.0262(10) Uiso 1 1 d G . . . .
H1 H 0.244050 0.702294 0.279712 0.031 Uiso 1 1 d G U . . .
C2 C 0.14962(5) 0.6815(3) 0.1904(2) 0.0282(12) Uiso 1 1 d G . . . .
C6 C 0.18756(6) 0.3296(4) 0.0670(2) 0.0329(13) Uiso 1 1 d G . . . .
H2 H 0.152105 0.808116 0.259473 0.039 Uiso 1 1 d G U . . .
C3 C 0.10477(6) 0.6647(4) 0.1093(3) 0.0310(12) Uiso 1 1 d G . . . .
H6 H 0.215658 0.215933 0.052278 0.037 Uiso 1 1 d G U . . .
C5 C 0.14306(7) 0.3153(5) -0.0136(2) 0.0403(15) Uiso 1 1 d G . . . .
C4 C 0.10178(6) 0.4803(4) 0.0069(3) 0.0349(13) Uiso 1 1 d G . . . .
C15 C 0.06217(6) 0.8332(5) 0.1335(3) 0.0354(13) Uiso 1 1 d G . . . .
H5 H 0.140906 0.190983 -0.083746 0.042 Uiso 1 1 d G U . . .
H4 H 0.071533 0.467735 -0.048510 0.042 Uiso 1 1 d G U . . .
C16 C 0.02683(7) 0.9744(5) 0.1538(3) 0.0467(17) Uiso 1 1 d G . . . .
H16 H -0.001291 1.086834 0.170042 0.056 Uiso 1 1 d G 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
C1 C2 1.3906 . ?
C1 C6 1.3953 . ?
C1 N1 1.4234 . ?
F4 C10 1.3429 . ?
C10 C9 1.3846 . ?
C10 C11 1.3890 . ?
C9 C8 1.3967 . ?
C9 H9 0.9504 . ?
C11 C12 1.3893 . ?
C11 C14 1.5168 . ?
C12 C13 1.3911 . ?
C12 H12 0.9502 . ?
C14 F1 1.3357 . ?
C14 F3 1.3359 . ?
C14 F2 1.3396 . ?
C8 C13 1.3938 . ?
C8 C7 1.5012 . ?
C13 H13 0.9505 . ?
C7 O1 1.2272 . ?
C7 N1 1.3522 . ?
N1 H1 0.8803 . ?
C2 C3 1.4022 . ?
C2 H2 0.9505 . ?
C6 C5 1.3916 . ?
C6 H6 0.9502 . ?
C3 C4 1.3973 . ?
C3 C15 1.4333 . ?
C5 C4 1.3877 . ?
C5 H5 0.9505 . ?
C4 H4 0.9504 . ?
C15 C16 1.1941 . ?
C16 H16 0.9503 . ?
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 C1 C6 120.5 . . ?
C2 C1 N1 117.4 . . ?
C6 C1 N1 122.1 . . ?
F4 C10 C9 118.5 . . ?
F4 C10 C11 119.2 . . ?
C9 C10 C11 122.4 . . ?
C10 C9 C8 118.2 . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
C10 C11 C12 119.0 . . ?
C10 C11 C14 120.1 . . ?
C12 C11 C14 121.0 . . ?
C11 C12 C13 119.8 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
F1 C14 F3 107.3 . . ?
F1 C14 F2 107.2 . . ?
F3 C14 F2 106.7 . . ?
F1 C14 C11 112.2 . . ?
F3 C14 C11 111.8 . . ?
F2 C14 C11 111.3 . . ?
C13 C8 C9 120.2 . . ?
C13 C8 C7 117.5 . . ?
C9 C8 C7 122.2 . . ?
C12 C13 C8 120.5 . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.7 . . ?
O1 C7 N1 123.9 . . ?
O1 C7 C8 120.8 . . ?
N1 C7 C8 115.2 . . ?
C7 N1 C1 124.8 . . ?
C7 N1 H1 117.6 . . ?
C1 N1 H1 117.6 . . ?
C1 C2 C3 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C5 C6 C1 119.3 . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
C4 C3 C2 119.5 . . ?
C4 C3 C15 120.6 . . ?
C2 C3 C15 119.8 . . ?
C4 C5 C6 120.9 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C4 C3 119.9 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.1 . . ?
C16 C15 C3 179.7 . . ?
C15 C16 H16 180.0 . . ?
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.058
_exptl_absorp_correction_type    none
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_source         'MX2 Beamline Australian Synchrotron'
####################################################################### 
# 
# 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_26
_database_code_depnum_ccdc_archive 'CCDC 1981930'
_audit_update_record             
;
2020-07-28 deposited with the CCDC.	2020-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H9 N O F4'
_chemical_formula_sum            'C16 H9 F4 N O'
_chemical_formula_weight         307.24
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_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.
;
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                   26.225(5)
_cell_length_b                   5.0070(10)
_cell_length_c                   10.259(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.37(3)
_cell_angle_gamma                90
_cell_volume                     1344.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    1191
_cell_measurement_theta_min      4.144
_cell_measurement_theta_max      29.094
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   0.349
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.710753083229
_diffrn_radiation_type           synchrotron
_diffrn_source                   synchrotron
_diffrn_measurement_device_type  'Dectris Eiger X 16M'
_diffrn_measurement_method       'Omega Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1191
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_theta_min         4.144
_diffrn_reflns_theta_max         29.094
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.243
_diffrn_measured_fraction_theta_full 0.253
_diffrn_reflns_Laue_measured_fraction_max 0.243
_diffrn_reflns_Laue_measured_fraction_full 0.253
_diffrn_reflns_point_group_measured_fraction_max 0.243
_diffrn_reflns_point_group_measured_fraction_full 0.253
_reflns_number_total             876
_reflns_number_gt                718
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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.
;
_computing_data_collection       'AS QEGUI'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'known structure'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1620P)²+1.9401P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         876
_refine_ls_number_parameters     29
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1258
_refine_ls_R_factor_gt           0.1147
_refine_ls_wR_factor_ref         0.3162
_refine_ls_wR_factor_gt          0.3037
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_restrained_S_all      1.161
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
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
C1 C 0.19053(5) 0.5128(3) 0.1695(2) 0.0285(12) Uiso 1 1 d G . . . .
F4 F 0.34894(5) 0.8858(4) 0.6406(2) 0.0390(10) Uiso 1 1 d G . . . .
C10 C 0.35082(4) 0.6829(3) 0.5555(2) 0.0290(12) Uiso 1 1 d G . . . .
C9 C 0.30748(4) 0.6249(3) 0.4769(2) 0.0280(12) Uiso 1 1 d G . . . .
C11 C 0.39602(4) 0.5405(3) 0.5484(2) 0.0291(12) Uiso 1 1 d G . . . .
C12 C 0.39778(5) 0.3307(3) 0.4601(2) 0.0319(13) Uiso 1 1 d G . . . .
C14 C 0.44265(5) 0.6164(3) 0.6350(2) 0.0337(13) Uiso 1 1 d G . . . .
C8 C 0.30958(4) 0.4124(2) 0.3893(2) 0.0273(12) Uiso 1 1 d G . . . .
H9 H 0.277121 0.726857 0.482551 0.033 Uiso 1 1 d G U . . .
C13 C 0.35441(5) 0.2650(3) 0.3821(2) 0.0304(13) Uiso 1 1 d G . . . .
H12 H 0.428495 0.232517 0.453116 0.037 Uiso 1 1 d G U . . .
F1 F 0.43204(6) 0.6379(4) 0.7603(2) 0.0478(12) Uiso 1 1 d G . . . .
F3 F 0.46234(5) 0.8496(4) 0.5996(3) 0.0397(10) Uiso 1 1 d G . . . .
F2 F 0.47982(5) 0.4342(4) 0.6286(3) 0.0415(11) Uiso 1 1 d G . . . .
C7 C 0.26477(5) 0.3349(3) 0.2993(2) 0.0273(11) Uiso 1 1 d G . . . .
H13 H 0.355346 0.118475 0.323355 0.033 Uiso 1 1 d G U . . .
O1 O 0.25707(6) 0.1006(3) 0.2693(3) 0.0343(11) Uiso 1 1 d G . . . .
N1 N 0.23513(5) 0.5400(3) 0.2545(2) 0.0278(11) Uiso 1 1 d G . . . .
H1 H 0.244079 0.702296 0.279652 0.033 Uiso 1 1 d G U . . .
C2 C 0.14966(5) 0.6814(3) 0.1902(3) 0.0304(13) Uiso 1 1 d G . . . .
C6 C 0.18766(6) 0.3299(4) 0.0667(2) 0.0329(13) Uiso 1 1 d G . . . .
H2 H 0.152125 0.807911 0.259366 0.040 Uiso 1 1 d G U . . .
C3 C 0.10482(6) 0.6646(4) 0.1091(3) 0.0327(13) Uiso 1 1 d G . . . .
H6 H 0.215763 0.216274 0.051989 0.039 Uiso 1 1 d G U . . .
C5 C 0.14317(7) 0.3156(5) -0.0140(3) 0.0406(16) Uiso 1 1 d G . . . .
C4 C 0.10187(7) 0.4804(4) 0.0066(3) 0.0364(14) Uiso 1 1 d G . . . .
C15 C 0.06221(6) 0.8330(5) 0.1333(3) 0.0374(15) Uiso 1 1 d G . . . .
H5 H 0.141032 0.191374 -0.084115 0.045 Uiso 1 1 d G U . . .
H4 H 0.071629 0.467877 -0.048834 0.045 Uiso 1 1 d G U . . .
C16 C 0.02685(7) 0.9741(6) 0.1537(4) 0.0495(18) Uiso 1 1 d G . . . .
H16 H -0.001284 1.086385 0.169902 0.059 Uiso 1 1 d G 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
C1 C2 1.3904 . ?
C1 C6 1.3952 . ?
C1 N1 1.4239 . ?
F4 C10 1.3426 . ?
C10 C9 1.3851 . ?
C10 C11 1.3889 . ?
C9 C8 1.3965 . ?
C9 H9 0.9503 . ?
C11 C12 1.3891 . ?
C11 C14 1.5173 . ?
C12 C13 1.3916 . ?
C12 H12 0.9501 . ?
C14 F1 1.3353 . ?
C14 F3 1.3356 . ?
C14 F2 1.3395 . ?
C8 C13 1.3938 . ?
C8 C7 1.5017 . ?
C13 H13 0.9504 . ?
C7 O1 1.2270 . ?
C7 N1 1.3523 . ?
N1 H1 0.8802 . ?
C2 C3 1.4027 . ?
C2 H2 0.9504 . ?
C6 C5 1.3921 . ?
C6 H6 0.9501 . ?
C3 C4 1.3972 . ?
C3 C15 1.4331 . ?
C5 C4 1.3875 . ?
C5 H5 0.9504 . ?
C4 H4 0.9507 . ?
C15 C16 1.1939 . ?
C16 H16 0.9502 . ?
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 C1 C6 120.4 . . ?
C2 C1 N1 117.4 . . ?
C6 C1 N1 122.1 . . ?
F4 C10 C9 118.5 . . ?
F4 C10 C11 119.1 . . ?
C9 C10 C11 122.4 . . ?
C10 C9 C8 118.2 . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
C10 C11 C12 118.9 . . ?
C10 C11 C14 120.1 . . ?
C12 C11 C14 121.0 . . ?
C11 C12 C13 119.8 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
F1 C14 F3 107.3 . . ?
F1 C14 F2 107.2 . . ?
F3 C14 F2 106.7 . . ?
F1 C14 C11 112.2 . . ?
F3 C14 C11 111.8 . . ?
F2 C14 C11 111.4 . . ?
C13 C8 C9 120.2 . . ?
C13 C8 C7 117.6 . . ?
C9 C8 C7 122.2 . . ?
C12 C13 C8 120.5 . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.7 . . ?
O1 C7 N1 123.9 . . ?
O1 C7 C8 120.8 . . ?
N1 C7 C8 115.2 . . ?
C7 N1 C1 124.8 . . ?
C7 N1 H1 117.6 . . ?
C1 N1 H1 117.6 . . ?
C1 C2 C3 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C5 C6 C1 119.3 . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.3 . . ?
C4 C3 C2 119.6 . . ?
C4 C3 C15 120.6 . . ?
C2 C3 C15 119.8 . . ?
C4 C5 C6 120.9 . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.6 . . ?
C5 C4 C3 119.9 . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C16 C15 C3 179.7 . . ?
C15 C16 H16 180.0 . . ?
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.059
_exptl_absorp_correction_type    none
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_source         'MX2 Beamline Australian Synchrotron'
####################################################################### 
# 
# 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_20
_database_code_depnum_ccdc_archive 'CCDC 1981927'
_audit_update_record             
;
2020-07-28 deposited with the CCDC.	2020-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H9 N O F4'
_chemical_formula_sum            'C16 H9 F4 N O'
_chemical_formula_weight         307.24
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_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.
;
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                   26.232(5)
_cell_length_b                   5.0080(10)
_cell_length_c                   10.264(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.43(3)
_cell_angle_gamma                90
_cell_volume                     1346.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    1233
_cell_measurement_theta_min      1.555
_cell_measurement_theta_max      29.118
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   0.350
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.710753083229
_diffrn_radiation_type           synchrotron
_diffrn_source                   synchrotron
_diffrn_measurement_device_type  'Dectris Eiger X 16M'
_diffrn_measurement_method       'Omega Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1233
_diffrn_reflns_av_unetI/netI     0.1040
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_theta_min         1.555
_diffrn_reflns_theta_max         29.118
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.256
_diffrn_measured_fraction_theta_full 0.270
_diffrn_reflns_Laue_measured_fraction_max 0.256
_diffrn_reflns_Laue_measured_fraction_full 0.270
_diffrn_reflns_point_group_measured_fraction_max 0.256
_diffrn_reflns_point_group_measured_fraction_full 0.270
_reflns_number_total             925
_reflns_number_gt                811
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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.
;
_computing_data_collection       'AS QEGUI'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'known structure'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1645P)²+2.5163P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         925
_refine_ls_number_parameters     29
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1238
_refine_ls_R_factor_gt           0.1172
_refine_ls_wR_factor_ref         0.3177
_refine_ls_wR_factor_gt          0.3095
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
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
C1 C 0.19046(5) 0.5124(3) 0.1698(2) 0.0261(11) Uiso 1 1 d G . . . .
F4 F 0.34903(5) 0.8865(4) 0.6404(2) 0.0378(10) Uiso 1 1 d G . . . .
C10 C 0.35085(4) 0.6831(3) 0.5555(2) 0.0301(13) Uiso 1 1 d G . . . .
C9 C 0.30748(4) 0.6251(3) 0.4770(2) 0.0292(12) Uiso 1 1 d G . . . .
C11 C 0.39602(4) 0.5405(3) 0.5484(2) 0.0282(12) Uiso 1 1 d G . . . .
C12 C 0.39772(4) 0.3303(3) 0.4604(2) 0.0292(12) Uiso 1 1 d G . . . .
C14 C 0.44268(4) 0.6165(3) 0.6349(2) 0.0314(12) Uiso 1 1 d G . . . .
C8 C 0.30952(4) 0.4122(2) 0.3895(2) 0.0258(11) Uiso 1 1 d G . . . .
H9 H 0.277151 0.727255 0.482547 0.031 Uiso 1 1 d G U . . .
C13 C 0.35432(5) 0.2645(3) 0.3824(2) 0.0285(12) Uiso 1 1 d G . . . .
H12 H 0.428416 0.231863 0.453420 0.034 Uiso 1 1 d G U . . .
F1 F 0.43210(5) 0.6385(4) 0.7602(2) 0.0440(11) Uiso 1 1 d G . . . .
F3 F 0.46241(5) 0.8494(3) 0.5993(3) 0.0370(9) Uiso 1 1 d G . . . .
F2 F 0.47981(4) 0.4340(4) 0.6286(3) 0.0411(11) Uiso 1 1 d G . . . .
C7 C 0.26468(4) 0.3346(2) 0.2997(2) 0.0255(11) Uiso 1 1 d G . . . .
H13 H 0.355221 0.117706 0.323861 0.031 Uiso 1 1 d G U . . .
O1 O 0.25694(6) 0.1002(3) 0.2699(3) 0.0315(10) Uiso 1 1 d G . . . .
N1 N 0.23508(4) 0.5397(3) 0.2547(2) 0.0258(10) Uiso 1 1 d G . . . .
H1 H 0.244067 0.702014 0.279708 0.031 Uiso 1 1 d G U . . .
C2 C 0.14963(5) 0.6813(3) 0.1904(2) 0.0280(12) Uiso 1 1 d G . . . .
C6 C 0.18753(6) 0.3290(4) 0.0672(2) 0.0317(13) Uiso 1 1 d G . . . .
H2 H 0.152132 0.808102 0.259430 0.038 Uiso 1 1 d G U . . .
C3 C 0.10477(6) 0.6645(4) 0.1094(3) 0.0292(12) Uiso 1 1 d G . . . .
H6 H 0.215611 0.215176 0.052564 0.035 Uiso 1 1 d G U . . .
C5 C 0.14302(7) 0.3147(5) -0.0134(2) 0.0390(15) Uiso 1 1 d G . . . .
C4 C 0.10177(6) 0.4798(4) 0.0071(3) 0.0349(13) Uiso 1 1 d G . . . .
C15 C 0.06220(6) 0.8332(5) 0.1334(3) 0.0366(14) Uiso 1 1 d G . . . .
H5 H 0.140851 0.190141 -0.083426 0.044 Uiso 1 1 d G U . . .
H4 H 0.071512 0.467221 -0.048336 0.044 Uiso 1 1 d G U . . .
C16 C 0.02688(7) 0.9746(6) 0.1537(4) 0.0457(17) Uiso 1 1 d G . . . .
H16 H -0.001235 1.087124 0.169874 0.055 Uiso 1 1 d G 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
C1 C2 1.3909 . ?
C1 C6 1.3956 . ?
C1 N1 1.4237 . ?
F4 C10 1.3431 . ?
C10 C9 1.3848 . ?
C10 C11 1.3893 . ?
C9 C8 1.3969 . ?
C9 H9 0.9506 . ?
C11 C12 1.3895 . ?
C11 C14 1.5170 . ?
C12 C13 1.3914 . ?
C12 H12 0.9504 . ?
C14 F3 1.3361 . ?
C14 F1 1.3363 . ?
C14 F2 1.3398 . ?
C8 C13 1.3942 . ?
C8 C7 1.5015 . ?
C13 H13 0.9507 . ?
C7 O1 1.2272 . ?
C7 N1 1.3523 . ?
N1 H1 0.8804 . ?
C2 C3 1.4024 . ?
C2 H2 0.9507 . ?
C6 C5 1.3918 . ?
C6 H6 0.9505 . ?
C3 C4 1.3976 . ?
C3 C15 1.4336 . ?
C5 C4 1.3880 . ?
C5 H5 0.9507 . ?
C4 H4 0.9505 . ?
C15 C16 1.1944 . ?
C16 H16 0.9505 . ?
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 C1 C6 120.5 . . ?
C2 C1 N1 117.4 . . ?
C6 C1 N1 122.1 . . ?
F4 C10 C9 118.5 . . ?
F4 C10 C11 119.2 . . ?
C9 C10 C11 122.4 . . ?
C10 C9 C8 118.2 . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
C10 C11 C12 119.0 . . ?
C10 C11 C14 120.1 . . ?
C12 C11 C14 121.0 . . ?
C11 C12 C13 119.8 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
F3 C14 F1 107.3 . . ?
F3 C14 F2 106.7 . . ?
F1 C14 F2 107.2 . . ?
F3 C14 C11 111.8 . . ?
F1 C14 C11 112.2 . . ?
F2 C14 C11 111.3 . . ?
C13 C8 C9 120.2 . . ?
C13 C8 C7 117.5 . . ?
C9 C8 C7 122.2 . . ?
C12 C13 C8 120.5 . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.7 . . ?
O1 C7 N1 123.9 . . ?
O1 C7 C8 120.8 . . ?
N1 C7 C8 115.2 . . ?
C7 N1 C1 124.8 . . ?
C7 N1 H1 117.6 . . ?
C1 N1 H1 117.6 . . ?
C1 C2 C3 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C5 C6 C1 119.3 . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
C4 C3 C2 119.5 . . ?
C4 C3 C15 120.7 . . ?
C2 C3 C15 119.8 . . ?
C4 C5 C6 120.9 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C4 C3 119.9 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.1 . . ?
C16 C15 C3 179.7 . . ?
C15 C16 H16 180.0 . . ?
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.062
_exptl_absorp_correction_type    none
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_source         'MX2 Beamline Australian Synchrotron'
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1989616'
loop_
_audit_author_name
_audit_author_address
'Deepak Chopra'
;IISER Bhopal
India
;
_audit_update_record             
;
2020-03-11 deposited with the CCDC.	2020-09-16 downloaded from the CCDC.
;
_audit_creation_date             2020-02-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H9 F4 N O'
_chemical_formula_sum            'C16 H9 F4 N O'
_chemical_formula_weight         307.24
_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 0.0033 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'
O O 0.0106 0.0060 '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'

_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                   26.2128(8)
_cell_length_b                   5.00270(10)
_cell_length_c                   10.2514(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.435(2)
_cell_angle_gamma                90
_cell_volume                     1341.90(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1937
_cell_measurement_temperature    100(2)
_cell_measurement_theta_min      3.89
_cell_measurement_theta_max      29.72
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6349
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14917
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.129
_diffrn_reflns_theta_min         2.335
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEXII D8 Venture CMOS diffractometer'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2801
_reflns_number_total             3929
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3929
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0543
_refine_ls_restrained_S_all      1.045
_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)+(0.0524P)²+0.3476P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1273
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9), C13(H13), C12(H12), C4(H4), C5(H5), C6(H6)
2.b :
 C16(H16)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.26488(5) 0.0391(3) 0.74546(13) 0.0156(3) Uani 1 1 d . . . . .
H1 H 0.2563(7) 0.194(4) 0.7234(18) 0.019 Uiso 1 1 d R . . . .
F1 F 0.06785(4) 0.1380(2) 0.23999(10) 0.0324(3) Uani 1 1 d . . . . .
F2 F 0.02020(4) -0.0659(2) 0.37082(11) 0.0323(3) Uani 1 1 d . . . . .
F3 F 0.03756(4) 0.3489(2) 0.40037(10) 0.0279(3) Uani 1 1 d . . . . .
F4 F 0.15096(4) 0.3861(2) 0.35961(10) 0.0267(3) Uani 1 1 d . . . . .
O1 O 0.24289(5) -0.4004(2) 0.73028(11) 0.0210(3) Uani 1 1 d . . . . .
C16 C 0.47305(8) 0.4719(4) 0.8461(2) 0.0362(5) Uani 1 1 d . . . . .
H16 H 0.501369 0.583086 0.829920 0.043 Uiso 1 1 calc R . . . .
C15 C 0.43783(7) 0.3336(4) 0.86624(18) 0.0260(4) Uani 1 1 d . . . . .
C3 C 0.39509(7) 0.1640(3) 0.89056(17) 0.0202(4) Uani 1 1 d . . . . .
C2 C 0.35029(6) 0.1804(3) 0.80995(16) 0.0174(3) Uani 1 1 d . . . . .
H2 H 0.347791 0.307114 0.740844 0.021 Uiso 1 1 calc R . . . .
C1 C 0.30954(6) 0.0127(3) 0.83040(15) 0.0152(3) Uani 1 1 d . . . . .
C7 C 0.23502(6) -0.1659(3) 0.70049(15) 0.0148(3) Uani 1 1 d . . . . .
C8 C 0.19031(6) -0.0873(3) 0.61085(15) 0.0144(3) Uani 1 1 d . . . . .
C9 C 0.19225(7) 0.1247(3) 0.52313(15) 0.0171(3) Uani 1 1 d . . . . .
H9 H 0.222565 0.226940 0.517273 0.020 Uiso 1 1 calc R . . . .
C10 C 0.14898(7) 0.1819(3) 0.44509(15) 0.0176(3) Uani 1 1 d . . . . .
C11 C 0.10378(6) 0.0408(3) 0.45138(15) 0.0172(3) Uani 1 1 d . . . . .
C14 C 0.05735(7) 0.1153(3) 0.36574(16) 0.0198(4) Uani 1 1 d . . . . .
C13 C 0.14554(7) -0.2348(3) 0.61741(16) 0.0180(3) Uani 1 1 d . . . . .
H13 H 0.144661 -0.382141 0.675692 0.022 Uiso 1 1 calc R . . . .
C12 C 0.10232(7) -0.1694(3) 0.54009(16) 0.0193(4) Uani 1 1 d . . . . .
H12 H 0.071642 -0.267845 0.547486 0.023 Uiso 1 1 calc R . . . .
C4 C 0.39810(7) -0.0213(4) 0.99289(17) 0.0243(4) Uani 1 1 d . . . . .
H4 H 0.428399 -0.034720 1.048158 0.029 Uiso 1 1 calc R . . . .
C5 C 0.35688(7) -0.1845(4) 1.01326(17) 0.0251(4) Uani 1 1 d . . . . .
H5 H 0.358899 -0.308038 1.083766 0.030 Uiso 1 1 calc R . . . .
C6 C 0.31255(7) -0.1713(3) 0.93256(16) 0.0208(4) Uani 1 1 d . . . . .
H6 H 0.284579 -0.286228 0.946797 0.025 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
N1 H1 0.836(19) . ?
N1 C1 1.423(2) . ?
N1 C7 1.354(2) . ?
F1 C14 1.339(2) . ?
F2 C14 1.334(2) . ?
F3 C14 1.3352(18) . ?
F4 C10 1.3489(18) . ?
O1 C7 1.2269(18) . ?
C16 H16 0.9500 . ?
C16 C15 1.182(3) . ?
C15 C3 1.439(3) . ?
C3 C2 1.397(2) . ?
C3 C4 1.399(2) . ?
C2 H2 0.9500 . ?
C2 C1 1.384(2) . ?
C1 C6 1.393(2) . ?
C7 C8 1.498(2) . ?
C8 C9 1.393(2) . ?
C8 C13 1.391(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.378(2) . ?
C10 C11 1.384(2) . ?
C11 C14 1.504(2) . ?
C11 C12 1.392(2) . ?
C13 H13 0.9500 . ?
C13 C12 1.382(2) . ?
C12 H12 0.9500 . ?
C4 H4 0.9500 . ?
C4 C5 1.380(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(3) . ?
C6 H6 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
C1 N1 H1 116.7(13) . . ?
C7 N1 H1 118.1(13) . . ?
C7 N1 C1 125.17(13) . . ?
C15 C16 H16 180.0 . . ?
C16 C15 C3 179.7(2) . . ?
C2 C3 C15 119.90(16) . . ?
C2 C3 C4 119.35(16) . . ?
C4 C3 C15 120.74(16) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 C3 120.25(15) . . ?
C1 C2 H2 119.9 . . ?
C2 C1 N1 117.73(14) . . ?
C2 C1 C6 120.33(15) . . ?
C6 C1 N1 121.93(15) . . ?
N1 C7 C8 115.18(13) . . ?
O1 C7 N1 123.67(15) . . ?
O1 C7 C8 121.15(14) . . ?
C9 C8 C7 122.55(15) . . ?
C13 C8 C7 117.55(14) . . ?
C13 C8 C9 119.90(15) . . ?
C8 C9 H9 120.9 . . ?
C10 C9 C8 118.16(15) . . ?
C10 C9 H9 120.9 . . ?
F4 C10 C9 118.15(15) . . ?
F4 C10 C11 118.87(14) . . ?
C9 C10 C11 122.97(15) . . ?
C10 C11 C14 120.76(15) . . ?
C10 C11 C12 118.20(15) . . ?
C12 C11 C14 121.04(15) . . ?
F1 C14 C11 112.16(14) . . ?
F2 C14 F1 106.72(13) . . ?
F2 C14 F3 106.74(14) . . ?
F2 C14 C11 112.08(14) . . ?
F3 C14 F1 106.70(13) . . ?
F3 C14 C11 112.05(13) . . ?
C8 C13 H13 119.6 . . ?
C12 C13 C8 120.75(15) . . ?
C12 C13 H13 119.6 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 119.98(16) . . ?
C13 C12 H12 120.0 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.74(16) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.12(16) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 H6 120.4 . . ?
C5 C6 C1 119.19(16) . . ?
C5 C6 H6 120.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C6 C5 -179.01(15) . . . . ?
N1 C7 C8 C9 34.6(2) . . . . ?
N1 C7 C8 C13 -145.41(15) . . . . ?
F4 C10 C11 C14 -0.7(2) . . . . ?
F4 C10 C11 C12 180.00(14) . . . . ?
O1 C7 C8 C9 -146.01(16) . . . . ?
O1 C7 C8 C13 34.0(2) . . . . ?
C15 C3 C2 C1 178.15(16) . . . . ?
C15 C3 C4 C5 -179.08(17) . . . . ?
C3 C2 C1 N1 179.82(14) . . . . ?
C3 C2 C1 C6 0.9(2) . . . . ?
C3 C4 C5 C6 1.0(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C2 C1 C6 C5 -0.1(2) . . . . ?
C1 N1 C7 O1 1.2(3) . . . . ?
C1 N1 C7 C8 -179.35(14) . . . . ?
C7 N1 C1 C2 142.64(16) . . . . ?
C7 N1 C1 C6 -38.4(2) . . . . ?
C7 C8 C9 C10 -179.76(14) . . . . ?
C7 C8 C13 C12 178.29(14) . . . . ?
C8 C9 C10 F4 -179.61(14) . . . . ?
C8 C9 C10 C11 0.9(2) . . . . ?
C8 C13 C12 C11 2.1(2) . . . . ?
C9 C8 C13 C12 -1.7(2) . . . . ?
C9 C10 C11 C14 178.76(15) . . . . ?
C9 C10 C11 C12 -0.5(2) . . . . ?
C10 C11 C14 F1 50.4(2) . . . . ?
C10 C11 C14 F2 170.48(14) . . . . ?
C10 C11 C14 F3 -69.5(2) . . . . ?
C10 C11 C12 C13 -1.0(2) . . . . ?
C14 C11 C12 C13 179.75(15) . . . . ?
C13 C8 C9 C10 0.2(2) . . . . ?
C12 C11 C14 F1 -130.33(16) . . . . ?
C12 C11 C14 F2 -10.3(2) . . . . ?
C12 C11 C14 F3 109.68(17) . . . . ?
C4 C3 C2 C1 -0.7(2) . . . . ?
C4 C5 C6 C1 -0.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_29
_database_code_depnum_ccdc_archive 'CCDC 1981933'
_audit_update_record             
;
2020-07-28 deposited with the CCDC.	2020-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H9 N O F4'
_chemical_formula_sum            'C16 H9 F4 N O'
_chemical_formula_weight         307.24
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_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.
;
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                   26.233(5)
_cell_length_b                   5.0070(10)
_cell_length_c                   10.266(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.36(3)
_cell_angle_gamma                90
_cell_volume                     1346.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    1189
_cell_measurement_theta_min      4.144
_cell_measurement_theta_max      29.129
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   0.350
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.710753083229
_diffrn_radiation_type           synchrotron
_diffrn_source                   synchrotron
_diffrn_measurement_device_type  'Dectris Eiger X 16M'
_diffrn_measurement_method       'Omega Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1189
_diffrn_reflns_av_unetI/netI     0.0925
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_theta_min         4.144
_diffrn_reflns_theta_max         29.129
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.245
_diffrn_measured_fraction_theta_full 0.258
_diffrn_reflns_Laue_measured_fraction_max 0.245
_diffrn_reflns_Laue_measured_fraction_full 0.258
_diffrn_reflns_point_group_measured_fraction_max 0.245
_diffrn_reflns_point_group_measured_fraction_full 0.258
_reflns_number_total             884
_reflns_number_gt                778
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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.
;
_computing_data_collection       'AS QEGUI'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'known structure'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1296P)²+2.3062P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         884
_refine_ls_number_parameters     29
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1161
_refine_ls_R_factor_gt           0.1087
_refine_ls_wR_factor_ref         0.2941
_refine_ls_wR_factor_gt          0.2847
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
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
C1 C 0.19049(5) 0.5125(3) 0.1697(2) 0.0291(11) Uiso 1 1 d G . . . .
F4 F 0.34904(5) 0.8861(4) 0.6405(2) 0.0406(9) Uiso 1 1 d G . . . .
C10 C 0.35087(4) 0.6830(3) 0.5555(2) 0.0329(12) Uiso 1 1 d G . . . .
C9 C 0.30751(4) 0.6249(2) 0.4770(2) 0.0322(12) Uiso 1 1 d G . . . .
C11 C 0.39605(4) 0.5404(3) 0.5484(2) 0.0320(12) Uiso 1 1 d G . . . .
C12 C 0.39777(4) 0.3304(3) 0.4603(2) 0.0335(12) Uiso 1 1 d G . . . .
C14 C 0.44271(4) 0.6164(3) 0.6349(2) 0.0350(13) Uiso 1 1 d G . . . .
C8 C 0.30957(4) 0.4122(2) 0.3895(2) 0.0294(11) Uiso 1 1 d G . . . .
H9 H 0.277168 0.727041 0.482600 0.035 Uiso 1 1 d G U . . .
C13 C 0.35438(5) 0.2646(3) 0.3823(2) 0.0322(12) Uiso 1 1 d G . . . .
H12 H 0.428471 0.232062 0.453268 0.039 Uiso 1 1 d G U . . .
F1 F 0.43212(5) 0.6382(4) 0.7602(2) 0.0480(11) Uiso 1 1 d G . . . .
F3 F 0.46242(5) 0.8494(3) 0.5994(3) 0.0410(9) Uiso 1 1 d G . . . .
F2 F 0.47985(5) 0.4340(4) 0.6285(3) 0.0446(11) Uiso 1 1 d G . . . .
C7 C 0.26473(4) 0.3347(2) 0.2996(2) 0.0291(11) Uiso 1 1 d G . . . .
H13 H 0.355286 0.117966 0.323659 0.035 Uiso 1 1 d G U . . .
O1 O 0.25700(6) 0.1003(3) 0.2697(3) 0.0348(10) Uiso 1 1 d G . . . .
N1 N 0.23512(4) 0.5398(3) 0.2547(2) 0.0292(10) Uiso 1 1 d G . . . .
H1 H 0.244086 0.702090 0.279750 0.035 Uiso 1 1 d G U . . .
C2 C 0.14965(5) 0.6813(3) 0.1904(2) 0.0318(12) Uiso 1 1 d G . . . .
C6 C 0.18758(6) 0.3293(4) 0.0671(2) 0.0360(13) Uiso 1 1 d G . . . .
H2 H 0.152144 0.807997 0.259513 0.043 Uiso 1 1 d G U . . .
C3 C 0.10480(6) 0.6645(4) 0.1094(3) 0.0337(12) Uiso 1 1 d G . . . .
H6 H 0.215669 0.215598 0.052400 0.040 Uiso 1 1 d G U . . .
C5 C 0.14307(7) 0.3150(5) -0.0135(3) 0.0445(16) Uiso 1 1 d G . . . .
C4 C 0.10180(6) 0.4800(4) 0.0070(3) 0.0385(13) Uiso 1 1 d G . . . .
C15 C 0.06221(6) 0.8331(5) 0.1335(3) 0.0392(14) Uiso 1 1 d G . . . .
H5 H 0.140911 0.190633 -0.083603 0.047 Uiso 1 1 d G U . . .
H4 H 0.071550 0.467485 -0.048398 0.047 Uiso 1 1 d G U . . .
C16 C 0.02688(7) 0.9744(5) 0.1539(4) 0.0490(17) Uiso 1 1 d G . . . .
H16 H -0.001243 1.086816 0.170071 0.059 Uiso 1 1 d G 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
C1 C2 1.3907 . ?
C1 C6 1.3957 . ?
C1 N1 1.4246 . ?
F4 C10 1.3430 . ?
C10 C9 1.3857 . ?
C10 C11 1.3892 . ?
C9 C8 1.3969 . ?
C9 H9 0.9505 . ?
C11 C12 1.3895 . ?
C11 C14 1.5179 . ?
C12 C13 1.3922 . ?
C12 H12 0.9503 . ?
C14 F3 1.3358 . ?
C14 F1 1.3362 . ?
C14 F2 1.3397 . ?
C8 C13 1.3941 . ?
C8 C7 1.5024 . ?
C13 H13 0.9506 . ?
C7 O1 1.2271 . ?
C7 N1 1.3525 . ?
N1 H1 0.8803 . ?
C2 C3 1.4033 . ?
C2 H2 0.9507 . ?
C6 C5 1.3927 . ?
C6 H6 0.9503 . ?
C3 C4 1.3977 . ?
C3 C15 1.4334 . ?
C5 C4 1.3878 . ?
C5 H5 0.9508 . ?
C4 H4 0.9511 . ?
C15 C16 1.1941 . ?
C16 H16 0.9503 . ?
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 C1 C6 120.4 . . ?
C2 C1 N1 117.4 . . ?
C6 C1 N1 122.1 . . ?
F4 C10 C9 118.5 . . ?
F4 C10 C11 119.1 . . ?
C9 C10 C11 122.4 . . ?
C10 C9 C8 118.2 . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
C10 C11 C12 118.9 . . ?
C10 C11 C14 120.1 . . ?
C12 C11 C14 121.0 . . ?
C11 C12 C13 119.8 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
F3 C14 F1 107.3 . . ?
F3 C14 F2 106.7 . . ?
F1 C14 F2 107.2 . . ?
F3 C14 C11 111.8 . . ?
F1 C14 C11 112.2 . . ?
F2 C14 C11 111.4 . . ?
C13 C8 C9 120.2 . . ?
C13 C8 C7 117.6 . . ?
C9 C8 C7 122.2 . . ?
C12 C13 C8 120.5 . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.7 . . ?
O1 C7 N1 123.9 . . ?
O1 C7 C8 120.8 . . ?
N1 C7 C8 115.3 . . ?
C7 N1 C1 124.8 . . ?
C7 N1 H1 117.6 . . ?
C1 N1 H1 117.6 . . ?
C1 C2 C3 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.1 . . ?
C5 C6 C1 119.3 . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.3 . . ?
C4 C3 C2 119.6 . . ?
C4 C3 C15 120.6 . . ?
C2 C3 C15 119.8 . . ?
C4 C5 C6 120.9 . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.6 . . ?
C5 C4 C3 119.9 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.1 . . ?
C16 C15 C3 179.7 . . ?
C15 C16 H16 180.0 . . ?
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.053
_exptl_absorp_correction_type    none
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_source         'MX2 Beamline Australian Synchrotron'

####################################################################### 
# 
# 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_24
_database_code_depnum_ccdc_archive 'CCDC 1981928'
_audit_update_record             
;
2020-07-28 deposited with the CCDC.	2020-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H9 N O F4'
_chemical_formula_sum            'C16 H9 F4 N O'
_chemical_formula_weight         307.24
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_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.
;
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                   26.219(5)
_cell_length_b                   5.0090(10)
_cell_length_c                   10.260(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.40(3)
_cell_angle_gamma                90
_cell_volume                     1345.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    1164
_cell_measurement_theta_min      4.142
_cell_measurement_theta_max      29.087
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   0.349
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.710753083229
_diffrn_radiation_type           synchrotron
_diffrn_source                   synchrotron
_diffrn_measurement_device_type  'Dectris Eiger X 16M'
_diffrn_measurement_method       'Omega Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1164
_diffrn_reflns_av_unetI/netI     0.1017
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_theta_min         4.142
_diffrn_reflns_theta_max         29.087
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.240
_diffrn_measured_fraction_theta_full 0.254
_diffrn_reflns_Laue_measured_fraction_max 0.240
_diffrn_reflns_Laue_measured_fraction_full 0.254
_diffrn_reflns_point_group_measured_fraction_max 0.240
_diffrn_reflns_point_group_measured_fraction_full 0.254
_reflns_number_total             864
_reflns_number_gt                766
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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.
;
_computing_data_collection       'AS QEGUI'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'known structure'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1584P)²+3.2215P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         864
_refine_ls_number_parameters     29
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1346
_refine_ls_R_factor_gt           0.1265
_refine_ls_wR_factor_ref         0.3447
_refine_ls_wR_factor_gt          0.3334
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.108
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
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
C1 C 0.19050(6) 0.5125(4) 0.1693(3) 0.0313(14) Uiso 1 1 d G . . . .
F4 F 0.34902(6) 0.8861(4) 0.6401(3) 0.0417(12) Uiso 1 1 d G . . . .
C10 C 0.35086(5) 0.6830(3) 0.5551(3) 0.0319(15) Uiso 1 1 d G . . . .
C9 C 0.30750(5) 0.6249(3) 0.4766(2) 0.0301(14) Uiso 1 1 d G . . . .
C11 C 0.39605(5) 0.5405(3) 0.5480(3) 0.0307(14) Uiso 1 1 d G . . . .
C12 C 0.39777(5) 0.3305(3) 0.4599(3) 0.0336(15) Uiso 1 1 d G . . . .
C14 C 0.44270(5) 0.6164(4) 0.6345(3) 0.0358(16) Uiso 1 1 d G . . . .
C8 C 0.30957(5) 0.4122(3) 0.3891(3) 0.0278(13) Uiso 1 1 d G . . . .
H9 H 0.277158 0.727025 0.482203 0.033 Uiso 1 1 d G U . . .
C13 C 0.35438(6) 0.2647(3) 0.3819(3) 0.0326(14) Uiso 1 1 d G . . . .
H12 H 0.428475 0.232162 0.452861 0.039 Uiso 1 1 d G U . . .
F1 F 0.43211(7) 0.6382(5) 0.7598(3) 0.0496(14) Uiso 1 1 d G . . . .
F3 F 0.46241(6) 0.8495(4) 0.5990(3) 0.0421(12) Uiso 1 1 d G . . . .
F2 F 0.47984(6) 0.4341(4) 0.6281(3) 0.0442(13) Uiso 1 1 d G . . . .
C7 C 0.26474(6) 0.3347(3) 0.2992(3) 0.0283(13) Uiso 1 1 d G . . . .
H13 H 0.355295 0.118055 0.323233 0.034 Uiso 1 1 d G U . . .
O1 O 0.25701(7) 0.1003(3) 0.2693(3) 0.0364(12) Uiso 1 1 d G . . . .
N1 N 0.23512(5) 0.5398(3) 0.2542(2) 0.0304(12) Uiso 1 1 d G . . . .
H1 H 0.244082 0.702115 0.279346 0.037 Uiso 1 1 d G U . . .
C2 C 0.14965(6) 0.6813(4) 0.1900(3) 0.0326(15) Uiso 1 1 d G . . . .
C6 C 0.18759(7) 0.3294(5) 0.0667(3) 0.0365(16) Uiso 1 1 d G . . . .
H2 H 0.152137 0.807964 0.259103 0.044 Uiso 1 1 d G U . . .
C3 C 0.10480(7) 0.6645(5) 0.1090(3) 0.0334(15) Uiso 1 1 d G . . . .
H6 H 0.215682 0.215676 0.051958 0.040 Uiso 1 1 d G U . . .
C5 C 0.14309(8) 0.3151(5) -0.0140(3) 0.0425(18) Uiso 1 1 d G . . . .
C4 C 0.10181(8) 0.4800(5) 0.0066(3) 0.0375(16) Uiso 1 1 d G . . . .
C15 C 0.06220(7) 0.8330(6) 0.1331(4) 0.0385(16) Uiso 1 1 d G . . . .
H5 H 0.140928 0.190701 -0.084059 0.046 Uiso 1 1 d G U . . .
H4 H 0.071559 0.467492 -0.048845 0.046 Uiso 1 1 d G U . . .
C16 C 0.02687(8) 0.9743(7) 0.1535(4) 0.052(2) Uiso 1 1 d G . . . .
H16 H -0.001256 1.086704 0.169656 0.063 Uiso 1 1 d G 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
C1 C2 1.3905 . ?
C1 C6 1.3955 . ?
C1 N1 1.4234 . ?
F4 C10 1.3430 . ?
C10 C9 1.3846 . ?
C10 C11 1.3888 . ?
C9 C8 1.3969 . ?
C9 H9 0.9503 . ?
C11 C12 1.3895 . ?
C11 C14 1.5168 . ?
C12 C13 1.3911 . ?
C12 H12 0.9500 . ?
C14 F1 1.3356 . ?
C14 F3 1.3361 . ?
C14 F2 1.3396 . ?
C8 C13 1.3937 . ?
C8 C7 1.5012 . ?
C13 H13 0.9506 . ?
C7 O1 1.2274 . ?
C7 N1 1.3523 . ?
N1 H1 0.8805 . ?
C2 C3 1.4021 . ?
C2 H2 0.9506 . ?
C6 C5 1.3915 . ?
C6 H6 0.9502 . ?
C3 C4 1.3975 . ?
C3 C15 1.4332 . ?
C5 C4 1.3876 . ?
C5 H5 0.9506 . ?
C4 H4 0.9504 . ?
C15 C16 1.1940 . ?
C16 H16 0.9502 . ?
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 C1 C6 120.5 . . ?
C2 C1 N1 117.4 . . ?
C6 C1 N1 122.1 . . ?
F4 C10 C9 118.5 . . ?
F4 C10 C11 119.2 . . ?
C9 C10 C11 122.3 . . ?
C10 C9 C8 118.2 . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
C10 C11 C12 119.0 . . ?
C10 C11 C14 120.1 . . ?
C12 C11 C14 121.0 . . ?
C11 C12 C13 119.8 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
F1 C14 F3 107.3 . . ?
F1 C14 F2 107.2 . . ?
F3 C14 F2 106.8 . . ?
F1 C14 C11 112.2 . . ?
F3 C14 C11 111.8 . . ?
F2 C14 C11 111.3 . . ?
C13 C8 C9 120.2 . . ?
C13 C8 C7 117.5 . . ?
C9 C8 C7 122.2 . . ?
C12 C13 C8 120.5 . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.7 . . ?
O1 C7 N1 123.9 . . ?
O1 C7 C8 120.8 . . ?
N1 C7 C8 115.2 . . ?
C7 N1 C1 124.8 . . ?
C7 N1 H1 117.6 . . ?
C1 N1 H1 117.6 . . ?
C1 C2 C3 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C5 C6 C1 119.3 . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
C4 C3 C2 119.6 . . ?
C4 C3 C15 120.7 . . ?
C2 C3 C15 119.8 . . ?
C4 C5 C6 120.9 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C4 C3 119.9 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.1 . . ?
C16 C15 C3 179.7 . . ?
C15 C16 H16 180.0 . . ?
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.066
_exptl_absorp_correction_type    none
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_source         'MX2 Beamline Australian Synchrotron'
####################################################################### 
# 
# 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_19
_database_code_depnum_ccdc_archive 'CCDC 1981926'
_audit_update_record             
;
2020-07-28 deposited with the CCDC.	2020-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H9 N O F4'
_chemical_formula_sum            'C16 H9 F4 N O'
_chemical_formula_weight         307.24
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_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.
;
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                   26.230(5)
_cell_length_b                   5.0080(10)
_cell_length_c                   10.263(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.46(3)
_cell_angle_gamma                90
_cell_volume                     1345.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    1243
_cell_measurement_theta_min      1.556
_cell_measurement_theta_max      29.114
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   0.350
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.710753083229
_diffrn_radiation_type           synchrotron
_diffrn_source                   synchrotron
_diffrn_measurement_device_type  'Dectris Eiger X 16M'
_diffrn_measurement_method       'Omega Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1243
_diffrn_reflns_av_unetI/netI     0.0742
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_theta_min         1.556
_diffrn_reflns_theta_max         29.114
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.257
_diffrn_measured_fraction_theta_full 0.271
_diffrn_reflns_Laue_measured_fraction_max 0.257
_diffrn_reflns_Laue_measured_fraction_full 0.271
_diffrn_reflns_point_group_measured_fraction_max 0.257
_diffrn_reflns_point_group_measured_fraction_full 0.271
_reflns_number_total             929
_reflns_number_gt                807
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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.
;
_computing_data_collection       'AS QEGUI'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'known structure'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1220P)²+2.3418P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         929
_refine_ls_number_parameters     29
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1082
_refine_ls_R_factor_gt           0.1017
_refine_ls_wR_factor_ref         0.2696
_refine_ls_wR_factor_gt          0.2625
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
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
C1 C 0.19047(5) 0.5126(3) 0.1698(2) 0.0249(10) Uiso 1 1 d G . . . .
F4 F 0.34900(5) 0.8862(3) 0.6406(2) 0.0377(9) Uiso 1 1 d G . . . .
C10 C 0.35083(4) 0.6830(3) 0.55562(19) 0.0288(11) Uiso 1 1 d G . . . .
C9 C 0.30747(3) 0.6250(2) 0.47712(18) 0.0275(10) Uiso 1 1 d G . . . .
C11 C 0.39601(4) 0.5404(2) 0.5485(2) 0.0271(11) Uiso 1 1 d G . . . .
C12 C 0.39772(4) 0.3303(3) 0.4604(2) 0.0277(11) Uiso 1 1 d G . . . .
C14 C 0.44266(4) 0.6163(3) 0.6351(2) 0.0313(11) Uiso 1 1 d G . . . .
C8 C 0.30952(4) 0.4122(2) 0.38959(19) 0.0243(10) Uiso 1 1 d G . . . .
H9 H 0.277132 0.727149 0.482677 0.029 Uiso 1 1 d G U . . .
C13 C 0.35433(4) 0.2646(3) 0.3824(2) 0.0281(11) Uiso 1 1 d G . . . .
H12 H 0.428415 0.231948 0.453463 0.034 Uiso 1 1 d G U . . .
F1 F 0.43207(5) 0.6382(4) 0.7604(2) 0.0446(10) Uiso 1 1 d G . . . .
F3 F 0.46239(4) 0.8493(3) 0.5996(2) 0.0371(8) Uiso 1 1 d G . . . .
F2 F 0.47979(4) 0.4339(3) 0.6287(2) 0.0404(10) Uiso 1 1 d G . . . .
C7 C 0.26469(4) 0.3347(2) 0.2997(2) 0.0249(10) Uiso 1 1 d G . . . .
H13 H 0.355233 0.117897 0.323833 0.030 Uiso 1 1 d G U . . .
O1 O 0.25695(5) 0.1003(2) 0.2698(2) 0.0312(9) Uiso 1 1 d G . . . .
N1 N 0.23509(4) 0.5399(2) 0.25474(19) 0.0251(9) Uiso 1 1 d G . . . .
H1 H 0.244063 0.702157 0.279817 0.030 Uiso 1 1 d G U . . .
C2 C 0.14963(5) 0.6815(3) 0.1905(2) 0.0278(11) Uiso 1 1 d G . . . .
C6 C 0.18755(6) 0.3294(4) 0.0672(2) 0.0312(11) Uiso 1 1 d G . . . .
H2 H 0.152127 0.808183 0.259528 0.037 Uiso 1 1 d G U . . .
C3 C 0.10478(5) 0.6647(4) 0.1094(2) 0.0291(11) Uiso 1 1 d G . . . .
H6 H 0.215638 0.215607 0.052502 0.035 Uiso 1 1 d G U . . .
C5 C 0.14305(6) 0.3151(4) -0.0135(2) 0.0381(14) Uiso 1 1 d G . . . .
C4 C 0.10179(6) 0.4802(4) 0.0071(2) 0.0341(12) Uiso 1 1 d G . . . .
C15 C 0.06220(5) 0.8333(4) 0.1335(3) 0.0358(13) Uiso 1 1 d G . . . .
H5 H 0.140888 0.190687 -0.083532 0.043 Uiso 1 1 d G U . . .
H4 H 0.071538 0.467649 -0.048386 0.043 Uiso 1 1 d G U . . .
C16 C 0.02687(6) 0.9747(5) 0.1538(3) 0.0450(15) Uiso 1 1 d G . . . .
H16 H -0.001243 1.087175 0.169989 0.054 Uiso 1 1 d G 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
C1 C2 1.3910 . ?
C1 C6 1.3955 . ?
C1 N1 1.4231 . ?
F4 C10 1.3431 . ?
C10 C9 1.3843 . ?
C10 C11 1.3893 . ?
C9 C8 1.3969 . ?
C9 H9 0.9506 . ?
C11 C12 1.3895 . ?
C11 C14 1.5164 . ?
C12 C13 1.3909 . ?
C12 H12 0.9504 . ?
C14 F3 1.3362 . ?
C14 F1 1.3363 . ?
C14 F2 1.3399 . ?
C8 C13 1.3941 . ?
C8 C7 1.5009 . ?
C13 H13 0.9506 . ?
C7 O1 1.2272 . ?
C7 N1 1.3521 . ?
N1 H1 0.8803 . ?
C2 C3 1.4018 . ?
C2 H2 0.9506 . ?
C6 C5 1.3913 . ?
C6 H6 0.9505 . ?
C3 C4 1.3975 . ?
C3 C15 1.4337 . ?
C5 C4 1.3880 . ?
C5 H5 0.9506 . ?
C4 H4 0.9501 . ?
C15 C16 1.1944 . ?
C16 H16 0.9505 . ?
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 C1 C6 120.5 . . ?
C2 C1 N1 117.4 . . ?
C6 C1 N1 122.1 . . ?
F4 C10 C9 118.5 . . ?
F4 C10 C11 119.2 . . ?
C9 C10 C11 122.3 . . ?
C10 C9 C8 118.2 . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
C10 C11 C12 119.0 . . ?
C10 C11 C14 120.1 . . ?
C12 C11 C14 120.9 . . ?
C11 C12 C13 119.7 . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.1 . . ?
F3 C14 F1 107.3 . . ?
F3 C14 F2 106.7 . . ?
F1 C14 F2 107.3 . . ?
F3 C14 C11 111.8 . . ?
F1 C14 C11 112.1 . . ?
F2 C14 C11 111.3 . . ?
C13 C8 C9 120.3 . . ?
C13 C8 C7 117.5 . . ?
C9 C8 C7 122.2 . . ?
C12 C13 C8 120.5 . . ?
C12 C13 H13 119.7 . . ?
C8 C13 H13 119.8 . . ?
O1 C7 N1 124.0 . . ?
O1 C7 C8 120.8 . . ?
N1 C7 C8 115.2 . . ?
C7 N1 C1 124.8 . . ?
C7 N1 H1 117.6 . . ?
C1 N1 H1 117.6 . . ?
C1 C2 C3 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C5 C6 C1 119.2 . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
C4 C3 C2 119.5 . . ?
C4 C3 C15 120.7 . . ?
C2 C3 C15 119.8 . . ?
C4 C5 C6 120.9 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C4 C3 119.9 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C16 C15 C3 179.7 . . ?
C15 C16 H16 180.0 . . ?
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.053
_exptl_absorp_correction_type    none
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_source         'MX2 Beamline Australian Synchrotron'
####################################################################### 
# 
# 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_27
_database_code_depnum_ccdc_archive 'CCDC 1981931'
_audit_update_record             
;
2020-07-28 deposited with the CCDC.	2020-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H9 N O F4'
_chemical_formula_sum            'C16 H9 F4 N O'
_chemical_formula_weight         307.24
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_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.
;
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                   26.226(5)
_cell_length_b                   5.0070(10)
_cell_length_c                   10.264(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.46(3)
_cell_angle_gamma                90
_cell_volume                     1345.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    1192
_cell_measurement_theta_min      4.144
_cell_measurement_theta_max      29.118
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   0.349
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.710753083229
_diffrn_radiation_type           synchrotron
_diffrn_source                   synchrotron
_diffrn_measurement_device_type  'Dectris Eiger X 16M'
_diffrn_measurement_method       'Omega Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1192
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_theta_min         4.144
_diffrn_reflns_theta_max         29.118
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.243
_diffrn_measured_fraction_theta_full 0.253
_diffrn_reflns_Laue_measured_fraction_max 0.243
_diffrn_reflns_Laue_measured_fraction_full 0.253
_diffrn_reflns_point_group_measured_fraction_max 0.243
_diffrn_reflns_point_group_measured_fraction_full 0.253
_reflns_number_total             878
_reflns_number_gt                740
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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.
;
_computing_data_collection       'AS QEGUI'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'known structure'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1416P)²+1.9289P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         878
_refine_ls_number_parameters     29
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1141
_refine_ls_R_factor_gt           0.1063
_refine_ls_wR_factor_ref         0.2908
_refine_ls_wR_factor_gt          0.2828
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_restrained_S_all      1.163
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
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
C1 C 0.19050(5) 0.5126(3) 0.1696(2) 0.0278(11) Uiso 1 1 d G . . . .
F4 F 0.34901(5) 0.8860(4) 0.6405(2) 0.0385(9) Uiso 1 1 d G . . . .
C10 C 0.35086(4) 0.6829(3) 0.5555(2) 0.0294(12) Uiso 1 1 d G . . . .
C9 C 0.30751(4) 0.6249(2) 0.4770(2) 0.0287(11) Uiso 1 1 d G . . . .
C11 C 0.39605(4) 0.5404(3) 0.5483(2) 0.0295(12) Uiso 1 1 d G . . . .
C12 C 0.39779(4) 0.3305(3) 0.4602(2) 0.0314(12) Uiso 1 1 d G . . . .
C14 C 0.44270(4) 0.6164(3) 0.6349(2) 0.0330(13) Uiso 1 1 d G . . . .
C8 C 0.30958(4) 0.4122(2) 0.3894(2) 0.0276(11) Uiso 1 1 d G . . . .
H9 H 0.277159 0.726932 0.482574 0.033 Uiso 1 1 d G U . . .
C13 C 0.35440(5) 0.2648(3) 0.3822(2) 0.0298(12) Uiso 1 1 d G . . . .
H12 H 0.428492 0.232249 0.453143 0.036 Uiso 1 1 d G U . . .
F1 F 0.43211(5) 0.6380(4) 0.7602(2) 0.0476(11) Uiso 1 1 d G . . . .
F3 F 0.46240(5) 0.8495(3) 0.5994(3) 0.0388(9) Uiso 1 1 d G . . . .
F2 F 0.47985(5) 0.4341(4) 0.6285(3) 0.0418(10) Uiso 1 1 d G . . . .
C7 C 0.26475(4) 0.3348(2) 0.2995(2) 0.0279(11) Uiso 1 1 d G . . . .
H13 H 0.355316 0.118169 0.323493 0.034 Uiso 1 1 d G U . . .
O1 O 0.25704(6) 0.1004(3) 0.2695(3) 0.0340(10) Uiso 1 1 d G . . . .
N1 N 0.23512(4) 0.5399(3) 0.2546(2) 0.0272(10) Uiso 1 1 d G . . . .
H1 H 0.244084 0.702149 0.279712 0.033 Uiso 1 1 d G U . . .
C2 C 0.14965(5) 0.6813(3) 0.1904(2) 0.0300(12) Uiso 1 1 d G . . . .
C6 C 0.18760(6) 0.3295(4) 0.0669(2) 0.0333(13) Uiso 1 1 d G . . . .
H2 H 0.152137 0.807920 0.259485 0.040 Uiso 1 1 d G U . . .
C3 C 0.10480(6) 0.6645(4) 0.1093(3) 0.0321(12) Uiso 1 1 d G . . . .
H6 H 0.215701 0.215861 0.052233 0.039 Uiso 1 1 d G U . . .
C5 C 0.14310(7) 0.3152(4) -0.0137(2) 0.0411(15) Uiso 1 1 d G . . . .
C4 C 0.10182(6) 0.4801(4) 0.0069(3) 0.0369(14) Uiso 1 1 d G . . . .
C15 C 0.06220(6) 0.8330(5) 0.1335(3) 0.0377(14) Uiso 1 1 d G . . . .
H5 H 0.140949 0.190917 -0.083789 0.045 Uiso 1 1 d G U . . .
H4 H 0.071571 0.467609 -0.048526 0.045 Uiso 1 1 d G U . . .
C16 C 0.02686(7) 0.9742(5) 0.1539(3) 0.0473(17) Uiso 1 1 d G . . . .
H16 H -0.001265 1.086572 0.170087 0.057 Uiso 1 1 d G 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
C1 C2 1.3907 . ?
C1 C6 1.3955 . ?
C1 N1 1.4231 . ?
F4 C10 1.3429 . ?
C10 C9 1.3843 . ?
C10 C11 1.3890 . ?
C9 C8 1.3968 . ?
C9 H9 0.9504 . ?
C11 C12 1.3894 . ?
C11 C14 1.5164 . ?
C12 C13 1.3908 . ?
C12 H12 0.9502 . ?
C14 F3 1.3359 . ?
C14 F1 1.3364 . ?
C14 F2 1.3396 . ?
C8 C13 1.3939 . ?
C8 C7 1.5009 . ?
C13 H13 0.9506 . ?
C7 O1 1.2270 . ?
C7 N1 1.3519 . ?
N1 H1 0.8802 . ?
C2 C3 1.4018 . ?
C2 H2 0.9506 . ?
C6 C5 1.3913 . ?
C6 H6 0.9503 . ?
C3 C4 1.3975 . ?
C3 C15 1.4334 . ?
C5 C4 1.3878 . ?
C5 H5 0.9506 . ?
C4 H4 0.9502 . ?
C15 C16 1.1942 . ?
C16 H16 0.9504 . ?
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 C1 C6 120.5 . . ?
C2 C1 N1 117.4 . . ?
C6 C1 N1 122.1 . . ?
F4 C10 C9 118.5 . . ?
F4 C10 C11 119.2 . . ?
C9 C10 C11 122.3 . . ?
C10 C9 C8 118.2 . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
C10 C11 C12 119.0 . . ?
C10 C11 C14 120.1 . . ?
C12 C11 C14 121.0 . . ?
C11 C12 C13 119.8 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
F3 C14 F1 107.3 . . ?
F3 C14 F2 106.7 . . ?
F1 C14 F2 107.3 . . ?
F3 C14 C11 111.8 . . ?
F1 C14 C11 112.2 . . ?
F2 C14 C11 111.3 . . ?
C13 C8 C9 120.2 . . ?
C13 C8 C7 117.5 . . ?
C9 C8 C7 122.2 . . ?
C12 C13 C8 120.5 . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?
O1 C7 N1 123.9 . . ?
O1 C7 C8 120.8 . . ?
N1 C7 C8 115.2 . . ?
C7 N1 C1 124.8 . . ?
C7 N1 H1 117.6 . . ?
C1 N1 H1 117.6 . . ?
C1 C2 C3 119.9 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C5 C6 C1 119.2 . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
C4 C3 C2 119.5 . . ?
C4 C3 C15 120.7 . . ?
C2 C3 C15 119.8 . . ?
C4 C5 C6 120.9 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C4 C3 119.9 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.1 . . ?
C16 C15 C3 179.7 . . ?
C15 C16 H16 180.0 . . ?
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.053
_exptl_absorp_correction_type    none
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_source         'MX2 Beamline Australian Synchrotron'
####################################################################### 
# 
# 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_16
_database_code_depnum_ccdc_archive 'CCDC 1981923'
_audit_update_record             
;
2020-07-28 deposited with the CCDC.	2020-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H9 N O F4'
_chemical_formula_sum            'C16 H9 F4 N O'
_chemical_formula_weight         307.24
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_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.
;
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                   26.229(5)
_cell_length_b                   5.0080(10)
_cell_length_c                   10.259(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.39(3)
_cell_angle_gamma                90
_cell_volume                     1345.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    1237
_cell_measurement_theta_min      1.555
_cell_measurement_theta_max      29.127
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   0.349
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.710753083229
_diffrn_radiation_type           synchrotron
_diffrn_source                   synchrotron
_diffrn_measurement_device_type  'Dectris Eiger X 16M'
_diffrn_measurement_method       'Omega Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1237
_diffrn_reflns_av_unetI/netI     0.0530
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_theta_min         1.555
_diffrn_reflns_theta_max         29.127
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.256
_diffrn_measured_fraction_theta_full 0.271
_diffrn_reflns_Laue_measured_fraction_max 0.256
_diffrn_reflns_Laue_measured_fraction_full 0.271
_diffrn_reflns_point_group_measured_fraction_max 0.256
_diffrn_reflns_point_group_measured_fraction_full 0.271
_reflns_number_total             925
_reflns_number_gt                796
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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.
;
_computing_data_collection       'AS QEGUI'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'known structure'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1266P)²+1.8377P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         925
_refine_ls_number_parameters     29
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1077
_refine_ls_R_factor_gt           0.0995
_refine_ls_wR_factor_ref         0.2670
_refine_ls_wR_factor_gt          0.2587
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_restrained_S_all      1.135
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
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
C1 C 0.19048(4) 0.5127(3) 0.1697(2) 0.0277(10) Uiso 1 1 d G . . . .
F4 F 0.34903(5) 0.8862(3) 0.6405(2) 0.0387(8) Uiso 1 1 d G . . . .
C10 C 0.35086(4) 0.6830(2) 0.55551(19) 0.0309(11) Uiso 1 1 d G . . . .
C9 C 0.30750(3) 0.6250(2) 0.47702(18) 0.0294(10) Uiso 1 1 d G . . . .
C11 C 0.39604(3) 0.5404(2) 0.5484(2) 0.0298(11) Uiso 1 1 d G . . . .
C12 C 0.39775(4) 0.3304(3) 0.4603(2) 0.0309(11) Uiso 1 1 d G . . . .
C14 C 0.44270(4) 0.6163(3) 0.6349(2) 0.0327(11) Uiso 1 1 d G . . . .
C8 C 0.30955(4) 0.4123(2) 0.38947(19) 0.0252(10) Uiso 1 1 d G . . . .
H9 H 0.277162 0.727134 0.482601 0.030 Uiso 1 1 d G U . . .
C13 C 0.35436(4) 0.2647(2) 0.3823(2) 0.0298(11) Uiso 1 1 d G . . . .
H12 H 0.428451 0.232034 0.453274 0.036 Uiso 1 1 d G U . . .
F1 F 0.43211(5) 0.6382(4) 0.7602(2) 0.0458(10) Uiso 1 1 d G . . . .
F3 F 0.46242(4) 0.8494(3) 0.5994(2) 0.0390(8) Uiso 1 1 d G . . . .
F2 F 0.47983(4) 0.4339(3) 0.6285(2) 0.0431(10) Uiso 1 1 d G . . . .
C7 C 0.26471(4) 0.3348(2) 0.2996(2) 0.0268(10) Uiso 1 1 d G . . . .
H13 H 0.355262 0.117992 0.323664 0.032 Uiso 1 1 d G U . . .
O1 O 0.25698(5) 0.1004(2) 0.2697(2) 0.0327(9) Uiso 1 1 d G . . . .
N1 N 0.23511(4) 0.5399(2) 0.25466(19) 0.0273(9) Uiso 1 1 d G . . . .
H1 H 0.244080 0.702205 0.279750 0.033 Uiso 1 1 d G U . . .
C2 C 0.14964(5) 0.6815(3) 0.1904(2) 0.0297(11) Uiso 1 1 d G . . . .
C6 C 0.18756(5) 0.3295(4) 0.0671(2) 0.0331(11) Uiso 1 1 d G . . . .
H2 H 0.152141 0.808185 0.259510 0.040 Uiso 1 1 d G U . . .
C3 C 0.10479(5) 0.6647(3) 0.1094(2) 0.0310(11) Uiso 1 1 d G . . . .
H6 H 0.215649 0.215730 0.052399 0.037 Uiso 1 1 d G U . . .
C5 C 0.14306(6) 0.3152(4) -0.0135(2) 0.0403(14) Uiso 1 1 d G . . . .
C4 C 0.10179(6) 0.4802(4) 0.0070(2) 0.0369(12) Uiso 1 1 d G . . . .
C15 C 0.06221(5) 0.8333(4) 0.1335(3) 0.0370(13) Uiso 1 1 d G . . . .
H5 H 0.140891 0.190821 -0.083604 0.044 Uiso 1 1 d G U . . .
H4 H 0.071538 0.467730 -0.048402 0.044 Uiso 1 1 d G U . . .
C16 C 0.02688(6) 0.9747(5) 0.1539(3) 0.0481(16) Uiso 1 1 d G . . . .
H16 H -0.001239 1.087126 0.170064 0.058 Uiso 1 1 d G 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
C1 C2 1.3907 . ?
C1 C6 1.3953 . ?
C1 N1 1.4238 . ?
F4 C10 1.3428 . ?
C10 C9 1.3850 . ?
C10 C11 1.3891 . ?
C9 C8 1.3966 . ?
C9 H9 0.9505 . ?
C11 C12 1.3892 . ?
C11 C14 1.5171 . ?
C12 C13 1.3915 . ?
C12 H12 0.9503 . ?
C14 F1 1.3355 . ?
C14 F3 1.3359 . ?
C14 F2 1.3397 . ?
C8 C13 1.3940 . ?
C8 C7 1.5016 . ?
C13 H13 0.9505 . ?
C7 O1 1.2272 . ?
C7 N1 1.3524 . ?
N1 H1 0.8804 . ?
C2 C3 1.4025 . ?
C2 H2 0.9504 . ?
C6 C5 1.3920 . ?
C6 H6 0.9503 . ?
C3 C4 1.3973 . ?
C3 C15 1.4334 . ?
C5 C4 1.3878 . ?
C5 H5 0.9505 . ?
C4 H4 0.9506 . ?
C15 C16 1.1942 . ?
C16 H16 0.9504 . ?
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 C1 C6 120.4 . . ?
C2 C1 N1 117.4 . . ?
C6 C1 N1 122.1 . . ?
F4 C10 C9 118.5 . . ?
F4 C10 C11 119.2 . . ?
C9 C10 C11 122.4 . . ?
C10 C9 C8 118.2 . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
C10 C11 C12 118.9 . . ?
C10 C11 C14 120.1 . . ?
C12 C11 C14 121.0 . . ?
C11 C12 C13 119.8 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
F1 C14 F3 107.3 . . ?
F1 C14 F2 107.2 . . ?
F3 C14 F2 106.7 . . ?
F1 C14 C11 112.2 . . ?
F3 C14 C11 111.8 . . ?
F2 C14 C11 111.4 . . ?
C13 C8 C9 120.2 . . ?
C13 C8 C7 117.6 . . ?
C9 C8 C7 122.2 . . ?
C12 C13 C8 120.5 . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.7 . . ?
O1 C7 N1 123.9 . . ?
O1 C7 C8 120.8 . . ?
N1 C7 C8 115.2 . . ?
C7 N1 C1 124.8 . . ?
C7 N1 H1 117.6 . . ?
C1 N1 H1 117.6 . . ?
C1 C2 C3 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C5 C6 C1 119.3 . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
C4 C3 C2 119.5 . . ?
C4 C3 C15 120.6 . . ?
C2 C3 C15 119.8 . . ?
C4 C5 C6 120.9 . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.6 . . ?
C5 C4 C3 119.9 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.1 . . ?
C16 C15 C3 179.7 . . ?
C15 C16 H16 180.0 . . ?
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.052
_exptl_absorp_correction_type    none
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_source         'MX2 Beamline Australian Synchrotron'
####################################################################### 
# 
# 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_25
_database_code_depnum_ccdc_archive 'CCDC 1981929'
_audit_update_record             
;
2020-07-28 deposited with the CCDC.	2020-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H9 N O F4'
_chemical_formula_sum            'C16 H9 F4 N O'
_chemical_formula_weight         307.24
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_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.
;
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                   26.223(5)
_cell_length_b                   5.0070(10)
_cell_length_c                   10.266(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.45(3)
_cell_angle_gamma                90
_cell_volume                     1345.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    1199
_cell_measurement_theta_min      4.144
_cell_measurement_theta_max      29.119
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   0.350
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.710753083229
_diffrn_radiation_type           synchrotron
_diffrn_source                   synchrotron
_diffrn_measurement_device_type  'Dectris Eiger X 16M'
_diffrn_measurement_method       'Omega Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1199
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_theta_min         4.144
_diffrn_reflns_theta_max         29.119
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.243
_diffrn_measured_fraction_theta_full 0.253
_diffrn_reflns_Laue_measured_fraction_max 0.243
_diffrn_reflns_Laue_measured_fraction_full 0.253
_diffrn_reflns_point_group_measured_fraction_max 0.243
_diffrn_reflns_point_group_measured_fraction_full 0.253
_reflns_number_total             879
_reflns_number_gt                733
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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.
;
_computing_data_collection       'AS QEGUI'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'known structure'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1701P)²+2.4464P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         879
_refine_ls_number_parameters     29
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1288
_refine_ls_R_factor_gt           0.1187
_refine_ls_wR_factor_ref         0.3253
_refine_ls_wR_factor_gt          0.3137
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_restrained_S_all      1.129
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
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
C1 C 0.19047(6) 0.5126(3) 0.1694(2) 0.0287(12) Uiso 1 1 d G . . . .
F4 F 0.34897(6) 0.8861(4) 0.6403(3) 0.0387(10) Uiso 1 1 d G . . . .
C10 C 0.35082(5) 0.6830(3) 0.5553(2) 0.0297(13) Uiso 1 1 d G . . . .
C9 C 0.30747(4) 0.6250(3) 0.4768(2) 0.0289(12) Uiso 1 1 d G . . . .
C11 C 0.39602(4) 0.5406(3) 0.5481(2) 0.0291(13) Uiso 1 1 d G . . . .
C12 C 0.39775(5) 0.3307(3) 0.4600(3) 0.0320(14) Uiso 1 1 d G . . . .
C14 C 0.44266(5) 0.6165(3) 0.6347(3) 0.0342(14) Uiso 1 1 d G . . . .
C8 C 0.30954(4) 0.4123(2) 0.3892(2) 0.0271(12) Uiso 1 1 d G . . . .
H9 H 0.277118 0.727015 0.482370 0.033 Uiso 1 1 d G U . . .
C13 C 0.35436(5) 0.2649(3) 0.3820(3) 0.0309(13) Uiso 1 1 d G . . . .
H12 H 0.428459 0.232376 0.452965 0.037 Uiso 1 1 d G U . . .
F1 F 0.43208(6) 0.6382(4) 0.7600(2) 0.0472(12) Uiso 1 1 d G . . . .
F3 F 0.46236(5) 0.8497(4) 0.5992(3) 0.0402(11) Uiso 1 1 d G . . . .
F2 F 0.47982(5) 0.4343(4) 0.6283(3) 0.0425(12) Uiso 1 1 d G . . . .
C7 C 0.26472(5) 0.3348(3) 0.2993(2) 0.0271(12) Uiso 1 1 d G . . . .
H13 H 0.355284 0.118246 0.323320 0.032 Uiso 1 1 d G U . . .
O1 O 0.25700(6) 0.1004(3) 0.2693(3) 0.0343(11) Uiso 1 1 d G . . . .
N1 N 0.23509(5) 0.5399(3) 0.2544(2) 0.0283(11) Uiso 1 1 d G . . . .
H1 H 0.244045 0.702180 0.279510 0.034 Uiso 1 1 d G U . . .
C2 C 0.14961(6) 0.6813(4) 0.1902(3) 0.0309(13) Uiso 1 1 d G . . . .
C6 C 0.18757(7) 0.3295(4) 0.0668(3) 0.0343(14) Uiso 1 1 d G . . . .
H2 H 0.152095 0.807916 0.259278 0.041 Uiso 1 1 d G U . . .
C3 C 0.10476(6) 0.6645(4) 0.1091(3) 0.0327(14) Uiso 1 1 d G . . . .
H6 H 0.215668 0.215837 0.052054 0.039 Uiso 1 1 d G U . . .
C5 C 0.14307(8) 0.3152(5) -0.0139(3) 0.0416(17) Uiso 1 1 d G . . . .
C4 C 0.10178(7) 0.4801(5) 0.0067(3) 0.0377(15) Uiso 1 1 d G . . . .
C15 C 0.06216(7) 0.8329(5) 0.1333(3) 0.0372(15) Uiso 1 1 d G . . . .
H5 H 0.140917 0.190840 -0.083967 0.045 Uiso 1 1 d G U . . .
H4 H 0.071534 0.467516 -0.048718 0.045 Uiso 1 1 d G U . . .
C16 C 0.02682(7) 0.9741(6) 0.1537(4) 0.0488(19) Uiso 1 1 d G . . . .
H16 H -0.001310 1.086498 0.169864 0.059 Uiso 1 1 d G 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
C1 C2 1.3906 . ?
C1 C6 1.3956 . ?
C1 N1 1.4232 . ?
F4 C10 1.3431 . ?
C10 C9 1.3844 . ?
C10 C11 1.3889 . ?
C9 C8 1.3969 . ?
C9 H9 0.9504 . ?
C11 C12 1.3895 . ?
C11 C14 1.5165 . ?
C12 C13 1.3909 . ?
C12 H12 0.9501 . ?
C14 F3 1.3359 . ?
C14 F1 1.3366 . ?
C14 F2 1.3395 . ?
C8 C13 1.3937 . ?
C8 C7 1.5010 . ?
C13 H13 0.9506 . ?
C7 O1 1.2270 . ?
C7 N1 1.3519 . ?
N1 H1 0.8802 . ?
C2 C3 1.4019 . ?
C2 H2 0.9507 . ?
C6 C5 1.3913 . ?
C6 H6 0.9503 . ?
C3 C4 1.3976 . ?
C3 C15 1.4333 . ?
C5 C4 1.3877 . ?
C5 H5 0.9507 . ?
C4 H4 0.9502 . ?
C15 C16 1.1941 . ?
C16 H16 0.9503 . ?
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 C1 C6 120.5 . . ?
C2 C1 N1 117.4 . . ?
C6 C1 N1 122.1 . . ?
F4 C10 C9 118.5 . . ?
F4 C10 C11 119.2 . . ?
C9 C10 C11 122.3 . . ?
C10 C9 C8 118.2 . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
C10 C11 C12 119.0 . . ?
C10 C11 C14 120.1 . . ?
C12 C11 C14 121.0 . . ?
C11 C12 C13 119.8 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
F3 C14 F1 107.3 . . ?
F3 C14 F2 106.7 . . ?
F1 C14 F2 107.2 . . ?
F3 C14 C11 111.8 . . ?
F1 C14 C11 112.2 . . ?
F2 C14 C11 111.3 . . ?
C13 C8 C9 120.2 . . ?
C13 C8 C7 117.5 . . ?
C9 C8 C7 122.2 . . ?
C12 C13 C8 120.5 . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?
O1 C7 N1 123.9 . . ?
O1 C7 C8 120.8 . . ?
N1 C7 C8 115.2 . . ?
C7 N1 C1 124.8 . . ?
C7 N1 H1 117.6 . . ?
C1 N1 H1 117.6 . . ?
C1 C2 C3 119.9 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C5 C6 C1 119.3 . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.4 . . ?
C4 C3 C2 119.5 . . ?
C4 C3 C15 120.7 . . ?
C2 C3 C15 119.8 . . ?
C4 C5 C6 120.9 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C4 C3 119.9 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.1 . . ?
C16 C15 C3 179.7 . . ?
C15 C16 H16 180.0 . . ?
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.061
_exptl_absorp_correction_type    none
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_source         'MX2 Beamline Australian Synchrotron'
####################################################################### 
# 
# 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_18
_database_code_depnum_ccdc_archive 'CCDC 1981925'
_audit_update_record             
;
2020-07-28 deposited with the CCDC.	2020-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H9 N O F4'
_chemical_formula_sum            'C16 H9 F4 N O'
_chemical_formula_weight         307.24
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_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.
;
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                   26.230(5)
_cell_length_b                   5.0080(10)
_cell_length_c                   10.263(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.49(3)
_cell_angle_gamma                90
_cell_volume                     1345.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    1240
_cell_measurement_theta_min      1.556
_cell_measurement_theta_max      29.109
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   0.350
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.710753083229
_diffrn_radiation_type           synchrotron
_diffrn_source                   synchrotron
_diffrn_measurement_device_type  'Dectris Eiger X 16M'
_diffrn_measurement_method       'Omega Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1240
_diffrn_reflns_av_unetI/netI     0.0680
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_theta_min         1.556
_diffrn_reflns_theta_max         29.109
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.257
_diffrn_measured_fraction_theta_full 0.270
_diffrn_reflns_Laue_measured_fraction_max 0.257
_diffrn_reflns_Laue_measured_fraction_full 0.270
_diffrn_reflns_point_group_measured_fraction_max 0.257
_diffrn_reflns_point_group_measured_fraction_full 0.270
_reflns_number_total             927
_reflns_number_gt                806
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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.
;
_computing_data_collection       'AS QEGUI'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'known structure'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1152P)²+2.4119P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         927
_refine_ls_number_parameters     29
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1081
_refine_ls_R_factor_gt           0.1011
_refine_ls_wR_factor_ref         0.2646
_refine_ls_wR_factor_gt          0.2576
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
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
C1 C 0.19047(5) 0.5127(3) 0.1697(2) 0.0259(10) Uiso 1 1 d G . . . .
F4 F 0.34898(5) 0.8859(3) 0.6406(2) 0.0373(9) Uiso 1 1 d G . . . .
C10 C 0.35083(4) 0.6828(3) 0.55557(19) 0.0294(11) Uiso 1 1 d G . . . .
C9 C 0.30747(3) 0.6248(2) 0.47705(18) 0.0276(10) Uiso 1 1 d G . . . .
C11 C 0.39602(4) 0.5403(3) 0.5484(2) 0.0282(11) Uiso 1 1 d G . . . .
C12 C 0.39775(4) 0.3304(3) 0.4602(2) 0.0288(11) Uiso 1 1 d G . . . .
C14 C 0.44267(4) 0.6162(3) 0.6350(2) 0.0314(11) Uiso 1 1 d G . . . .
C8 C 0.30954(4) 0.4122(2) 0.38943(19) 0.0243(10) Uiso 1 1 d G . . . .
H9 H 0.277127 0.726879 0.482657 0.029 Uiso 1 1 d G U . . .
C13 C 0.35436(4) 0.2647(3) 0.3822(2) 0.0281(11) Uiso 1 1 d G . . . .
H12 H 0.428450 0.232125 0.453202 0.034 Uiso 1 1 d G U . . .
F1 F 0.43208(5) 0.6378(4) 0.7603(2) 0.0446(10) Uiso 1 1 d G . . . .
F3 F 0.46237(4) 0.8493(3) 0.5995(2) 0.0370(8) Uiso 1 1 d G . . . .
F2 F 0.47981(4) 0.4339(3) 0.6285(2) 0.0413(10) Uiso 1 1 d G . . . .
C7 C 0.26471(4) 0.3348(2) 0.2996(2) 0.0257(10) Uiso 1 1 d G . . . .
H13 H 0.355273 0.118116 0.323541 0.031 Uiso 1 1 d G U . . .
O1 O 0.25699(5) 0.1004(2) 0.2695(2) 0.0314(9) Uiso 1 1 d G . . . .
N1 N 0.23509(4) 0.5399(2) 0.25465(19) 0.0254(9) Uiso 1 1 d G . . . .
H1 H 0.244052 0.702166 0.279792 0.031 Uiso 1 1 d G U . . .
C2 C 0.14962(5) 0.6814(3) 0.1905(2) 0.0283(11) Uiso 1 1 d G . . . .
C6 C 0.18757(6) 0.3296(4) 0.0670(2) 0.0318(12) Uiso 1 1 d G . . . .
H2 H 0.152107 0.807989 0.259567 0.038 Uiso 1 1 d G U . . .
C3 C 0.10477(5) 0.6646(4) 0.1094(2) 0.0293(11) Uiso 1 1 d G . . . .
H6 H 0.215661 0.215951 0.052281 0.035 Uiso 1 1 d G U . . .
C5 C 0.14307(6) 0.3154(4) -0.0136(2) 0.0393(14) Uiso 1 1 d G . . . .
C4 C 0.10179(6) 0.4803(4) 0.0070(2) 0.0349(12) Uiso 1 1 d G . . . .
C15 C 0.06217(6) 0.8331(4) 0.1336(3) 0.0360(13) Uiso 1 1 d G . . . .
H5 H 0.140910 0.191081 -0.083747 0.043 Uiso 1 1 d G U . . .
H4 H 0.071536 0.467799 -0.048470 0.043 Uiso 1 1 d G U . . .
C16 C 0.02684(6) 0.9744(5) 0.1540(3) 0.0458(15) Uiso 1 1 d G . . . .
H16 H -0.001289 1.086743 0.170179 0.055 Uiso 1 1 d G 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
C1 C2 1.3911 . ?
C1 C6 1.3955 . ?
C1 N1 1.4227 . ?
F4 C10 1.3431 . ?
C10 C9 1.3840 . ?
C10 C11 1.3893 . ?
C9 C8 1.3969 . ?
C9 H9 0.9506 . ?
C11 C12 1.3895 . ?
C11 C14 1.5161 . ?
C12 C13 1.3905 . ?
C12 H12 0.9504 . ?
C14 F3 1.3362 . ?
C14 F1 1.3364 . ?
C14 F2 1.3399 . ?
C8 C13 1.3941 . ?
C8 C7 1.5005 . ?
C13 H13 0.9507 . ?
C7 O1 1.2272 . ?
C7 N1 1.3520 . ?
N1 H1 0.8803 . ?
C2 C3 1.4015 . ?
C2 H2 0.9506 . ?
C6 C5 1.3909 . ?
C6 H6 0.9505 . ?
C3 C4 1.3975 . ?
C3 C15 1.4338 . ?
C5 C4 1.3881 . ?
C5 H5 0.9506 . ?
C4 H4 0.9499 . ?
C15 C16 1.1945 . ?
C16 H16 0.9506 . ?
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 C1 C6 120.5 . . ?
C2 C1 N1 117.4 . . ?
C6 C1 N1 122.1 . . ?
F4 C10 C9 118.5 . . ?
F4 C10 C11 119.2 . . ?
C9 C10 C11 122.3 . . ?
C10 C9 C8 118.2 . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 121.0 . . ?
C10 C11 C12 119.0 . . ?
C10 C11 C14 120.1 . . ?
C12 C11 C14 120.9 . . ?
C11 C12 C13 119.7 . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.1 . . ?
F3 C14 F1 107.3 . . ?
F3 C14 F2 106.7 . . ?
F1 C14 F2 107.3 . . ?
F3 C14 C11 111.8 . . ?
F1 C14 C11 112.1 . . ?
F2 C14 C11 111.3 . . ?
C13 C8 C9 120.3 . . ?
C13 C8 C7 117.5 . . ?
C9 C8 C7 122.2 . . ?
C12 C13 C8 120.5 . . ?
C12 C13 H13 119.7 . . ?
C8 C13 H13 119.8 . . ?
O1 C7 N1 124.0 . . ?
O1 C7 C8 120.8 . . ?
N1 C7 C8 115.2 . . ?
C7 N1 C1 124.8 . . ?
C7 N1 H1 117.6 . . ?
C1 N1 H1 117.6 . . ?
C1 C2 C3 119.9 . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.0 . . ?
C5 C6 C1 119.2 . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
C4 C3 C2 119.5 . . ?
C4 C3 C15 120.7 . . ?
C2 C3 C15 119.8 . . ?
C4 C5 C6 120.9 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.5 . . ?
C5 C4 C3 119.9 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C16 C15 C3 179.7 . . ?
C15 C16 H16 180.0 . . ?
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.052
_exptl_absorp_correction_type    none
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_source         'MX2 Beamline Australian Synchrotron'
####################################################################### 
# 
# 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_28
_database_code_depnum_ccdc_archive 'CCDC 1981932'
_audit_update_record             
;
2020-07-28 deposited with the CCDC.	2020-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H9 N O F4'
_chemical_formula_sum            'C16 H9 F4 N O'
_chemical_formula_weight         307.24
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_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.
;
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                   26.231(5)
_cell_length_b                   5.0080(10)
_cell_length_c                   10.259(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.42(3)
_cell_angle_gamma                90
_cell_volume                     1345.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    1174
_cell_measurement_theta_min      4.143
_cell_measurement_theta_max      29.124
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   0.349
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.710753083229
_diffrn_radiation_type           synchrotron
_diffrn_source                   synchrotron
_diffrn_measurement_device_type  'Dectris Eiger X 16M'
_diffrn_measurement_method       'Omega Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1174
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_theta_min         4.143
_diffrn_reflns_theta_max         29.124
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.241
_diffrn_measured_fraction_theta_full 0.253
_diffrn_reflns_Laue_measured_fraction_max 0.241
_diffrn_reflns_Laue_measured_fraction_full 0.253
_diffrn_reflns_point_group_measured_fraction_max 0.241
_diffrn_reflns_point_group_measured_fraction_full 0.253
_reflns_number_total             869
_reflns_number_gt                740
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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.
;
_computing_data_collection       'AS QEGUI'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'known structure'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1256P)²+2.1403P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         869
_refine_ls_number_parameters     29
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1092
_refine_ls_R_factor_gt           0.1010
_refine_ls_wR_factor_ref         0.2705
_refine_ls_wR_factor_gt          0.2630
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_restrained_S_all      1.129
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
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
C1 C 0.19048(5) 0.5128(3) 0.1698(2) 0.0279(11) Uiso 1 1 d G . . . .
F4 F 0.34899(5) 0.8858(3) 0.6407(2) 0.0387(9) Uiso 1 1 d G . . . .
C10 C 0.35085(4) 0.6829(3) 0.5556(2) 0.0301(11) Uiso 1 1 d G . . . .
C9 C 0.30749(4) 0.6249(2) 0.47710(19) 0.0289(11) Uiso 1 1 d G . . . .
C11 C 0.39605(4) 0.5405(3) 0.5484(2) 0.0293(11) Uiso 1 1 d G . . . .
C12 C 0.39779(4) 0.3308(3) 0.4602(2) 0.0311(12) Uiso 1 1 d G . . . .
C14 C 0.44269(4) 0.6164(3) 0.6350(2) 0.0331(12) Uiso 1 1 d G . . . .
C8 C 0.30957(4) 0.4124(2) 0.3894(2) 0.0271(11) Uiso 1 1 d G . . . .
H9 H 0.277136 0.726861 0.482747 0.033 Uiso 1 1 d G U . . .
C13 C 0.35440(4) 0.2650(3) 0.3821(2) 0.0303(11) Uiso 1 1 d G . . . .
H12 H 0.428502 0.232551 0.453102 0.036 Uiso 1 1 d G U . . .
F1 F 0.43211(5) 0.6379(4) 0.7603(2) 0.0468(10) Uiso 1 1 d G . . . .
F3 F 0.46238(5) 0.8497(3) 0.5996(2) 0.0403(9) Uiso 1 1 d G . . . .
F2 F 0.47986(4) 0.4342(3) 0.6285(2) 0.0426(10) Uiso 1 1 d G . . . .
C7 C 0.26475(4) 0.3349(2) 0.2995(2) 0.0277(10) Uiso 1 1 d G . . . .
H13 H 0.355328 0.118500 0.323436 0.033 Uiso 1 1 d G U . . .
O1 O 0.25705(6) 0.1006(2) 0.2695(3) 0.0337(9) Uiso 1 1 d G . . . .
N1 N 0.23510(4) 0.5400(2) 0.2547(2) 0.0281(10) Uiso 1 1 d G . . . .
H1 H 0.244053 0.702301 0.279886 0.034 Uiso 1 1 d G U . . .
C2 C 0.14962(5) 0.6814(3) 0.1906(2) 0.0295(12) Uiso 1 1 d G . . . .
C6 C 0.18759(6) 0.3299(4) 0.0670(2) 0.0342(12) Uiso 1 1 d G . . . .
H2 H 0.152098 0.807899 0.259724 0.041 Uiso 1 1 d G U . . .
C3 C 0.10477(5) 0.6646(4) 0.1095(3) 0.0317(12) Uiso 1 1 d G . . . .
H6 H 0.215694 0.216281 0.052251 0.038 Uiso 1 1 d G U . . .
C5 C 0.14309(7) 0.3156(4) -0.0136(2) 0.0409(15) Uiso 1 1 d G . . . .
C4 C 0.10179(6) 0.4804(4) 0.0071(2) 0.0358(13) Uiso 1 1 d G . . . .
C15 C 0.06215(6) 0.8329(4) 0.1338(3) 0.0379(13) Uiso 1 1 d G . . . .
H5 H 0.140937 0.191372 -0.083756 0.046 Uiso 1 1 d G U . . .
H4 H 0.071542 0.467861 -0.048378 0.046 Uiso 1 1 d G U . . .
C16 C 0.02681(6) 0.9741(5) 0.1542(3) 0.0478(16) Uiso 1 1 d G . . . .
H16 H -0.001328 1.086346 0.170468 0.057 Uiso 1 1 d G 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
C1 C2 1.3909 . ?
C1 C6 1.3952 . ?
C1 N1 1.4235 . ?
F4 C10 1.3428 . ?
C10 C9 1.3847 . ?
C10 C11 1.3892 . ?
C9 C8 1.3967 . ?
C9 H9 0.9506 . ?
C11 C12 1.3893 . ?
C11 C14 1.5168 . ?
C12 C13 1.3912 . ?
C12 H12 0.9503 . ?
C14 F1 1.3356 . ?
C14 F3 1.3360 . ?
C14 F2 1.3398 . ?
C8 C13 1.3941 . ?
C8 C7 1.5013 . ?
C13 H13 0.9505 . ?
C7 O1 1.2272 . ?
C7 N1 1.3523 . ?
N1 H1 0.8803 . ?
C2 C3 1.4022 . ?
C2 H2 0.9504 . ?
C6 C5 1.3916 . ?
C6 H6 0.9504 . ?
C3 C4 1.3973 . ?
C3 C15 1.4336 . ?
C5 C4 1.3879 . ?
C5 H5 0.9504 . ?
C4 H4 0.9504 . ?
C15 C16 1.1943 . ?
C16 H16 0.9505 . ?
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 C1 C6 120.5 . . ?
C2 C1 N1 117.4 . . ?
C6 C1 N1 122.1 . . ?
F4 C10 C9 118.5 . . ?
F4 C10 C11 119.2 . . ?
C9 C10 C11 122.4 . . ?
C10 C9 C8 118.2 . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
C10 C11 C12 119.0 . . ?
C10 C11 C14 120.1 . . ?
C12 C11 C14 120.9 . . ?
C11 C12 C13 119.8 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
F1 C14 F3 107.3 . . ?
F1 C14 F2 107.2 . . ?
F3 C14 F2 106.7 . . ?
F1 C14 C11 112.1 . . ?
F3 C14 C11 111.8 . . ?
F2 C14 C11 111.4 . . ?
C13 C8 C9 120.2 . . ?
C13 C8 C7 117.6 . . ?
C9 C8 C7 122.2 . . ?
C12 C13 C8 120.5 . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.7 . . ?
O1 C7 N1 123.9 . . ?
O1 C7 C8 120.8 . . ?
N1 C7 C8 115.2 . . ?
C7 N1 C1 124.8 . . ?
C7 N1 H1 117.6 . . ?
C1 N1 H1 117.6 . . ?
C1 C2 C3 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C5 C6 C1 119.2 . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
C4 C3 C2 119.5 . . ?
C4 C3 C15 120.7 . . ?
C2 C3 C15 119.8 . . ?
C4 C5 C6 120.9 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C4 C3 119.9 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.1 . . ?
C16 C15 C3 179.7 . . ?
C15 C16 H16 180.0 . . ?
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.049
_exptl_absorp_correction_type    none
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_source         'MX2 Beamline Australian Synchrotron'
####################################################################### 
# 
# 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_17
_database_code_depnum_ccdc_archive 'CCDC 1981924'
_audit_update_record             
;
2020-07-28 deposited with the CCDC.	2020-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H9 N O F4'
_chemical_formula_sum            'C16 H9 F4 N O'
_chemical_formula_weight         307.24
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_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.
;
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                   26.231(5)
_cell_length_b                   5.0080(10)
_cell_length_c                   10.262(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.44(3)
_cell_angle_gamma                90
_cell_volume                     1345.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    1230
_cell_measurement_theta_min      1.555
_cell_measurement_theta_max      29.118
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   0.350
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.710753083229
_diffrn_radiation_type           synchrotron
_diffrn_source                   synchrotron
_diffrn_measurement_device_type  'Dectris Eiger X 16M'
_diffrn_measurement_method       'Omega Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1230
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_theta_min         1.555
_diffrn_reflns_theta_max         29.118
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.256
_diffrn_measured_fraction_theta_full 0.270
_diffrn_reflns_Laue_measured_fraction_max 0.256
_diffrn_reflns_Laue_measured_fraction_full 0.270
_diffrn_reflns_point_group_measured_fraction_max 0.256
_diffrn_reflns_point_group_measured_fraction_full 0.270
_reflns_number_total             923
_reflns_number_gt                808
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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.
;
_computing_data_collection       'AS QEGUI'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'known structure'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1199P)²+2.4258P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         923
_refine_ls_number_parameters     29
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1072
_refine_ls_R_factor_gt           0.1006
_refine_ls_wR_factor_ref         0.2627
_refine_ls_wR_factor_gt          0.2567
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
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
C1 C 0.19046(5) 0.5126(3) 0.1697(2) 0.0263(10) Uiso 1 1 d G . . . .
F4 F 0.34900(5) 0.8861(3) 0.6406(2) 0.0383(9) Uiso 1 1 d G . . . .
C10 C 0.35083(4) 0.6829(3) 0.55556(19) 0.0296(11) Uiso 1 1 d G . . . .
C9 C 0.30747(3) 0.6249(2) 0.47707(19) 0.0279(10) Uiso 1 1 d G . . . .
C11 C 0.39601(4) 0.5404(2) 0.5484(2) 0.0295(11) Uiso 1 1 d G . . . .
C12 C 0.39773(4) 0.3304(3) 0.4603(2) 0.0301(11) Uiso 1 1 d G . . . .
C14 C 0.44267(4) 0.6163(3) 0.6350(2) 0.0326(12) Uiso 1 1 d G . . . .
C8 C 0.30953(4) 0.4122(2) 0.38950(19) 0.0249(10) Uiso 1 1 d G . . . .
H9 H 0.277131 0.727033 0.482647 0.030 Uiso 1 1 d G U . . .
C13 C 0.35434(4) 0.2646(3) 0.3823(2) 0.0292(11) Uiso 1 1 d G . . . .
H12 H 0.428431 0.232024 0.453306 0.035 Uiso 1 1 d G U . . .
F1 F 0.43208(5) 0.6381(4) 0.7603(2) 0.0450(10) Uiso 1 1 d G . . . .
F3 F 0.46238(4) 0.8493(3) 0.5995(2) 0.0381(8) Uiso 1 1 d G . . . .
F2 F 0.47981(4) 0.4339(3) 0.6286(2) 0.0416(10) Uiso 1 1 d G . . . .
C7 C 0.26470(4) 0.3347(2) 0.2996(2) 0.0260(10) Uiso 1 1 d G . . . .
H13 H 0.355246 0.117983 0.323677 0.031 Uiso 1 1 d G U . . .
O1 O 0.25697(5) 0.1003(2) 0.2697(2) 0.0321(9) Uiso 1 1 d G . . . .
N1 N 0.23508(4) 0.5399(2) 0.25469(19) 0.0263(9) Uiso 1 1 d G . . . .
H1 H 0.244054 0.702148 0.279790 0.032 Uiso 1 1 d G U . . .
C2 C 0.14962(5) 0.6814(3) 0.1905(2) 0.0286(11) Uiso 1 1 d G . . . .
C6 C 0.18755(6) 0.3295(4) 0.0671(2) 0.0319(11) Uiso 1 1 d G . . . .
H2 H 0.152113 0.808084 0.259545 0.038 Uiso 1 1 d G U . . .
C3 C 0.10477(5) 0.6646(4) 0.1094(2) 0.0296(11) Uiso 1 1 d G . . . .
H6 H 0.215637 0.215728 0.052402 0.036 Uiso 1 1 d G U . . .
C5 C 0.14304(6) 0.3152(4) -0.0135(2) 0.0401(14) Uiso 1 1 d G . . . .
C4 C 0.10178(6) 0.4802(4) 0.0070(2) 0.0356(12) Uiso 1 1 d G . . . .
C15 C 0.06218(6) 0.8332(4) 0.1335(3) 0.0369(13) Uiso 1 1 d G . . . .
H5 H 0.140883 0.190820 -0.083615 0.044 Uiso 1 1 d G U . . .
H4 H 0.071523 0.467679 -0.048401 0.044 Uiso 1 1 d G U . . .
C16 C 0.02685(6) 0.9745(5) 0.1539(3) 0.0464(15) Uiso 1 1 d G . . . .
H16 H -0.001270 1.086967 0.170097 0.056 Uiso 1 1 d G 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
C1 C2 1.3910 . ?
C1 C6 1.3955 . ?
C1 N1 1.4233 . ?
F4 C10 1.3430 . ?
C10 C9 1.3846 . ?
C10 C11 1.3893 . ?
C9 C8 1.3968 . ?
C9 H9 0.9506 . ?
C11 C12 1.3894 . ?
C11 C14 1.5167 . ?
C12 C13 1.3911 . ?
C12 H12 0.9504 . ?
C14 F3 1.3361 . ?
C14 F1 1.3361 . ?
C14 F2 1.3399 . ?
C8 C13 1.3941 . ?
C8 C7 1.5011 . ?
C13 H13 0.9506 . ?
C7 O1 1.2272 . ?
C7 N1 1.3522 . ?
N1 H1 0.8803 . ?
C2 C3 1.4021 . ?
C2 H2 0.9506 . ?
C6 C5 1.3915 . ?
C6 H6 0.9505 . ?
C3 C4 1.3975 . ?
C3 C15 1.4336 . ?
C5 C4 1.3880 . ?
C5 H5 0.9506 . ?
C4 H4 0.9503 . ?
C15 C16 1.1944 . ?
C16 H16 0.9505 . ?
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 C1 C6 120.5 . . ?
C2 C1 N1 117.4 . . ?
C6 C1 N1 122.1 . . ?
F4 C10 C9 118.5 . . ?
F4 C10 C11 119.2 . . ?
C9 C10 C11 122.3 . . ?
C10 C9 C8 118.2 . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
C10 C11 C12 119.0 . . ?
C10 C11 C14 120.1 . . ?
C12 C11 C14 121.0 . . ?
C11 C12 C13 119.8 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
F3 C14 F1 107.3 . . ?
F3 C14 F2 106.7 . . ?
F1 C14 F2 107.2 . . ?
F3 C14 C11 111.8 . . ?
F1 C14 C11 112.1 . . ?
F2 C14 C11 111.3 . . ?
C13 C8 C9 120.2 . . ?
C13 C8 C7 117.5 . . ?
C9 C8 C7 122.2 . . ?
C12 C13 C8 120.5 . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?
O1 C7 N1 123.9 . . ?
O1 C7 C8 120.8 . . ?
N1 C7 C8 115.2 . . ?
C7 N1 C1 124.8 . . ?
C7 N1 H1 117.6 . . ?
C1 N1 H1 117.6 . . ?
C1 C2 C3 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C5 C6 C1 119.2 . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
C4 C3 C2 119.5 . . ?
C4 C3 C15 120.7 . . ?
C2 C3 C15 119.8 . . ?
C4 C5 C6 120.9 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C4 C3 119.9 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C16 C15 C3 179.7 . . ?
C15 C16 H16 180.0 . . ?
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.052
_exptl_absorp_correction_type    none
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_source         'MX2 Beamline Australian Synchrotron'
