# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_10
_database_code_depnum_ccdc_archive 'CCDC 1562522'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7CE01872J 2017
_audit_update_record             
;
2017-07-17 deposited with the CCDC.
2018-01-10 downloaded from the CCDC.
;
_audit_creation_date             2016-12-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H12 F4 N2'
_chemical_formula_sum            'C20 H12 F4 N2'
_chemical_formula_weight         356.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H12 N2 F4'
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'

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

_cell_length_a                   10.0684(6)
_cell_length_b                   3.7580(2)
_cell_length_c                   20.6855(12)
_cell_angle_alpha                90
_cell_angle_beta                 91.012(5)
_cell_angle_gamma                90
_cell_volume                     782.56(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2953
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      32.8870
_cell_measurement_theta_min      3.4940
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44448
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.7d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            9408
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         32.713
_diffrn_reflns_theta_min         3.552
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.9970
_diffrn_measured_fraction_theta_max 0.9541
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00 118.80   0.30   10.00    --   29.89  54.00-120.00  626
  2  ω    -69.00 118.80   0.30   10.00    --   29.89  54.00   0.00  626
  3  ω    -69.00  72.00   0.30   10.00    --   29.89  54.00 120.00  470
;
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0566418000
_diffrn_orient_matrix_UB_12      -0.0486658000
_diffrn_orient_matrix_UB_13      0.0178943000
_diffrn_orient_matrix_UB_21      -0.0389794000
_diffrn_orient_matrix_UB_22      -0.0010642000
_diffrn_orient_matrix_UB_23      -0.0288885000
_diffrn_orient_matrix_UB_31      0.0153478000
_diffrn_orient_matrix_UB_32      -0.1824085000
_diffrn_orient_matrix_UB_33      -0.0045899000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2260
_reflns_number_total             2761
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.7d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7d (Rigaku OD, 2015)'
_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         0.751
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2761
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0666
_refine_ls_restrained_S_all      1.148
_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)+(0.1114P)²+0.2062P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1784
_refine_ls_wR_factor_ref         0.2000
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C1(H1), C10(H10), C3(H3), C5(H5), C7(H7)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.44312(9) 0.7359(3) 0.20035(4) 0.0314(3) Uani 1 1 d . . . . .
F2 F 0.74046(8) 0.3112(3) 0.35925(4) 0.0309(3) Uani 1 1 d . . . . .
N1 N 0.32758(11) 0.8076(3) 0.42470(5) 0.0229(3) Uani 1 1 d . . . . .
C2 C 0.41362(12) 0.7049(4) 0.37485(6) 0.0212(3) Uani 1 1 d . . . . .
C9 C -0.03336(12) 0.8335(4) 0.44180(6) 0.0213(3) Uani 1 1 d . . . . .
H9 H -0.0553 0.7221 0.4029 0.026 Uiso 1 1 calc R . . . .
C1 C 0.20232(13) 0.7658(3) 0.41418(6) 0.0213(3) Uani 1 1 d . . . . .
H1 H 0.1748 0.6526 0.3763 0.026 Uiso 1 1 calc R . . . .
C10 C -0.13362(12) 0.9449(4) 0.48245(6) 0.0210(3) Uani 1 1 d . . . . .
H10 H -0.2222 0.9084 0.4708 0.025 Uiso 1 1 calc R . . . .
C3 C 0.38194(12) 0.7679(4) 0.30952(6) 0.0220(3) Uani 1 1 d . . . . .
H3 H 0.3014 0.8714 0.2974 0.026 Uiso 1 1 calc R . . . .
C4 C 0.47367(13) 0.6721(4) 0.26354(6) 0.0223(3) Uani 1 1 d . . . . .
C5 C 0.59476(12) 0.5174(4) 0.27799(6) 0.0224(3) Uani 1 1 d . . . . .
H5 H 0.6544 0.4548 0.2461 0.027 Uiso 1 1 calc R . . . .
C8 C 0.10074(12) 0.8876(4) 0.45893(6) 0.0203(3) Uani 1 1 d . . . . .
C6 C 0.62203(12) 0.4610(4) 0.34327(6) 0.0229(3) Uani 1 1 d . . . . .
C7 C 0.53633(12) 0.5527(4) 0.39218(6) 0.0231(3) Uani 1 1 d . . . . .
H7 H 0.5595 0.5143 0.4353 0.028 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C4 1.3589(14) . ?
F2 C6 1.3543(14) . ?
N1 C2 1.4121(16) . ?
N1 C1 1.2856(16) . ?
C2 C3 1.4031(17) . ?
C2 C7 1.4023(17) . ?
C9 H9 0.9300 . ?
C9 C10 1.3898(17) . ?
C9 C8 1.4046(16) . ?
C1 H1 0.9300 . ?
C1 C8 1.4649(17) . ?
C10 H10 0.9300 . ?
C10 C8 1.4007(17) 3_576 ?
C3 H3 0.9300 . ?
C3 C4 1.3851(18) . ?
C4 C5 1.3787(17) . ?
C5 H5 0.9300 . ?
C5 C6 1.3893(17) . ?
C8 C10 1.4007(17) 3_576 ?
C6 C7 1.3849(18) . ?
C7 H7 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 117.10(11) . . ?
C3 C2 N1 121.69(12) . . ?
C7 C2 N1 118.28(11) . . ?
C7 C2 C3 119.95(11) . . ?
C10 C9 H9 119.7 . . ?
C10 C9 C8 120.60(11) . . ?
C8 C9 H9 119.7 . . ?
N1 C1 H1 118.4 . . ?
N1 C1 C8 123.27(11) . . ?
C8 C1 H1 118.4 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C8 119.74(11) . 3_576 ?
C8 C10 H10 120.1 3_576 . ?
C2 C3 H3 120.8 . . ?
C4 C3 C2 118.33(12) . . ?
C4 C3 H3 120.8 . . ?
F1 C4 C3 118.18(11) . . ?
F1 C4 C5 117.87(11) . . ?
C5 C4 C3 123.96(12) . . ?
C4 C5 H5 122.1 . . ?
C4 C5 C6 115.71(12) . . ?
C6 C5 H5 122.1 . . ?
C9 C8 C1 118.31(11) . . ?
C10 C8 C9 119.65(11) 3_576 . ?
C10 C8 C1 122.04(11) 3_576 . ?
F2 C6 C5 117.30(11) . . ?
F2 C6 C7 118.84(11) . . ?
C7 C6 C5 123.86(12) . . ?
C2 C7 H7 120.9 . . ?
C6 C7 C2 118.18(11) . . ?
C6 C7 H7 120.9 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.601
_oxdiff_exptl_absorpt_empirical_full_min 0.540
####################################################################### 
# 
# 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_12
_database_code_depnum_ccdc_archive 'CCDC 1562523'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7CE01872J 2017
_audit_update_record             
;
2017-07-17 deposited with the CCDC.
2018-01-10 downloaded from the CCDC.
;
_audit_creation_date             2016-12-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H14 F2 N2'
_chemical_formula_sum            'C20 H14 F2 N2'
_chemical_formula_weight         320.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H14 N2 F2'
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'
N N 0.0061 0.0033 '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'

_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                   6.9111(5)
_cell_length_b                   11.5037(9)
_cell_length_c                   10.0653(7)
_cell_angle_alpha                90
_cell_angle_beta                 104.659(8)
_cell_angle_gamma                90
_cell_volume                     774.18(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2262
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      32.9320
_cell_measurement_theta_min      2.7130
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.7f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0768
_diffrn_reflns_av_unetI/netI     0.0797
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6483
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         32.935
_diffrn_reflns_theta_min         2.741
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.9189
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00 119.70   0.30   10.00    --   29.89  54.00 120.00  629
  2  ω    -69.00  90.90   0.30   10.00    --   29.89  54.00   0.00  533
;
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0909897000
_diffrn_orient_matrix_UB_12      0.0004620000
_diffrn_orient_matrix_UB_13      -0.0521947000
_diffrn_orient_matrix_UB_21      -0.0543377000
_diffrn_orient_matrix_UB_22      0.0042044000
_diffrn_orient_matrix_UB_23      0.0507707000
_diffrn_orient_matrix_UB_31      0.0042450000
_diffrn_orient_matrix_UB_32      0.0615396000
_diffrn_orient_matrix_UB_33      -0.0030585000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1693
_reflns_number_total             2674
_reflns_odcompleteness_completeness 91.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.86
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.728
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       0.010(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         2674
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1126
_refine_ls_R_factor_gt           0.0857
_refine_ls_restrained_S_all      1.020
_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)+(0.1618P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2189
_refine_ls_wR_factor_ref         0.2711
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9), C7(H7), C1(H1), C4(H4), C5(H5), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.15178(16) 0.67792(9) 0.42178(10) 0.0368(4) Uani 1 1 d . . . . .
N1 N 0.36600(19) 0.43989(13) 0.72029(12) 0.0269(4) Uani 1 1 d . . . . .
C10 C 0.4531(2) 0.60581(15) 1.05031(14) 0.0265(4) Uani 1 1 d . . . . .
H10 H 0.4217 0.6786 1.0843 0.032 Uiso 1 1 calc R . . . .
C8 C 0.4290(2) 0.47424(14) 0.85940(15) 0.0257(4) Uani 1 1 d . . . . .
C2 C 0.2444(2) 0.48332(15) 0.48215(14) 0.0255(4) Uani 1 1 d . . . . .
C9 C 0.3815(2) 0.57997(15) 0.91176(14) 0.0274(4) Uani 1 1 d . . . . .
H9 H 0.2997 0.6346 0.8521 0.033 Uiso 1 1 calc R . . . .
C3 C 0.1712(2) 0.56689(15) 0.38154(15) 0.0275(4) Uani 1 1 d . . . . .
C7 C 0.2602(3) 0.37017(15) 0.43662(16) 0.0292(4) Uani 1 1 d . . . . .
H7 H 0.3092 0.3107 0.5020 0.035 Uiso 1 1 calc R . . . .
C1 C 0.3088(2) 0.51618(15) 0.62685(15) 0.0258(4) Uani 1 1 d . . . . .
H1 H 0.3080 0.5958 0.6517 0.031 Uiso 1 1 calc R . . . .
C4 C 0.1155(2) 0.54212(17) 0.24256(15) 0.0316(4) Uani 1 1 d . . . . .
H4 H 0.0653 0.6013 0.1771 0.038 Uiso 1 1 calc R . . . .
C5 C 0.1348(3) 0.42900(18) 0.20135(15) 0.0329(4) Uani 1 1 d . . . . .
H5 H 0.0993 0.4103 0.1063 0.039 Uiso 1 1 calc R . . . .
C6 C 0.2057(3) 0.34226(17) 0.29759(17) 0.0330(4) Uani 1 1 d . . . . .
H6 H 0.2170 0.2645 0.2686 0.040 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C3 1.357(2) . ?
N1 C8 1.4135(18) . ?
N1 C1 1.274(2) . ?
C10 H10 0.9500 . ?
C10 C8 1.401(2) 3_667 ?
C10 C9 1.3887(19) . ?
C8 C10 1.401(2) 3_667 ?
C8 C9 1.397(2) . ?
C2 C3 1.395(2) . ?
C2 C7 1.393(2) . ?
C2 C1 1.461(2) . ?
C9 H9 0.9500 . ?
C3 C4 1.383(2) . ?
C7 H7 0.9500 . ?
C7 C6 1.392(2) . ?
C1 H1 0.9500 . ?
C4 H4 0.9500 . ?
C4 C5 1.382(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(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 C8 119.94(15) . . ?
C8 C10 H10 119.6 3_667 . ?
C9 C10 H10 119.6 . . ?
C9 C10 C8 120.76(16) . 3_667 ?
C10 C8 N1 116.21(15) 3_667 . ?
C9 C8 N1 125.03(14) . . ?
C9 C8 C10 118.76(13) . 3_667 ?
C3 C2 C1 120.56(15) . . ?
C7 C2 C3 116.69(14) . . ?
C7 C2 C1 122.69(15) . . ?
C10 C9 C8 120.47(15) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
F1 C3 C2 118.49(14) . . ?
F1 C3 C4 118.20(15) . . ?
C4 C3 C2 123.31(17) . . ?
C2 C7 H7 119.2 . . ?
C6 C7 C2 121.50(16) . . ?
C6 C7 H7 119.2 . . ?
N1 C1 C2 121.14(16) . . ?
N1 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
C3 C4 H4 120.9 . . ?
C5 C4 C3 118.30(16) . . ?
C5 C4 H4 120.9 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.67(15) . . ?
C6 C5 H5 119.7 . . ?
C7 C6 H6 120.2 . . ?
C5 C6 C7 119.53(17) . . ?
C5 C6 H6 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C3 C4 C5 -179.88(13) . . . . ?
N1 C8 C9 C10 -179.31(15) . . . . ?
C10 C8 C9 C10 1.1(3) 3_667 . . . ?
C8 N1 C1 C2 179.50(14) . . . . ?
C8 C10 C9 C8 -1.2(3) 3_667 . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C2 C7 C6 C5 0.3(3) . . . . ?
C3 C2 C7 C6 0.1(3) . . . . ?
C3 C2 C1 N1 176.29(15) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
C7 C2 C3 F1 179.39(14) . . . . ?
C7 C2 C3 C4 0.0(3) . . . . ?
C7 C2 C1 N1 -6.6(3) . . . . ?
C1 N1 C8 C10 -160.34(15) . . . 3_667 ?
C1 N1 C8 C9 20.1(3) . . . . ?
C1 C2 C3 F1 -3.3(2) . . . . ?
C1 C2 C3 C4 177.31(15) . . . . ?
C1 C2 C7 C6 -177.16(15) . . . . ?
C4 C5 C6 C7 -0.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.251
_oxdiff_exptl_absorpt_empirical_full_min 0.440
####################################################################### 
# 
# 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 1562529'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7CE01872J 2017
_audit_update_record             
;
2017-07-17 deposited with the CCDC.
2018-01-10 downloaded from the CCDC.
;
_audit_creation_date             2016-12-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H12 F4 N2'
_chemical_formula_sum            'C20 H12 F4 N2'
_chemical_formula_weight         356.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.056(2)
_cell_length_b                   6.677(2)
_cell_length_c                   8.101(3)
_cell_angle_alpha                79.582(6)
_cell_angle_beta                 75.757(7)
_cell_angle_gamma                77.750(7)
_cell_volume                     307.41(17)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2540
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.62
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0405 before and 0.0299 after correction.
The Ratio of minimum to maximum transmission is 0.9305.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.925
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             182
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4136
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.123
_diffrn_reflns_theta_min         2.618
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                983
_reflns_number_total             1073
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1073
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0397
_refine_ls_restrained_S_all      1.092
_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)+(0.0614P)²+0.1894P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1080
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C1(H1), C9(H9), C10(H10), C7(H7)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3915(2) 0.2608(2) 0.72159(19) 0.0176(4) Uani 1 1 d . . . . .
C3 C 0.2601(3) 0.5157(3) 0.9594(2) 0.0173(4) Uani 1 1 d . . . . .
H3 H 0.2932 0.5808 0.8439 0.021 Uiso 1 1 calc R . . . .
C2 C 0.2807(3) 0.3171(3) 0.9943(2) 0.0168(4) Uani 1 1 d . . . . .
C6 C 0.1740(3) 0.3424(3) 1.2747(2) 0.0211(4) Uani 1 1 d . . . . .
H6 H 0.1442 0.2792 1.3910 0.025 Uiso 1 1 calc R . . . .
C4 C 0.1951(3) 0.6210(3) 1.0820(2) 0.0186(4) Uani 1 1 d . . . . .
C1 C 0.3447(3) 0.1958(3) 0.8683(2) 0.0176(4) Uani 1 1 d . . . . .
H1 H 0.3524 0.0508 0.8997 0.021 Uiso 1 1 calc R . . . .
C5 C 0.1535(3) 0.5368(3) 1.2378(2) 0.0195(4) Uani 1 1 d . . . . .
C9 C 0.6100(3) 0.1494(3) 0.4813(2) 0.0193(4) Uani 1 1 d . . . . .
H9 H 0.6909 0.2610 0.4660 0.023 Uiso 1 1 calc R . . . .
C10 C 0.6687(3) 0.0214(3) 0.3715(2) 0.0193(4) Uani 1 1 d . . . . .
H10 H 0.7955 0.0365 0.2769 0.023 Uiso 1 1 calc R . . . .
C8 C 0.4429(3) 0.1278(3) 0.6115(2) 0.0176(4) Uani 1 1 d . . . . .
C7 C 0.2359(3) 0.2333(3) 1.1515(2) 0.0193(4) Uani 1 1 d . . . . .
H7 H 0.2492 0.0872 1.1768 0.023 Uiso 1 1 calc R . . . .
F2 F 0.09207(18) 0.65051(17) 1.35259(13) 0.0246(3) Uani 1 1 d . . . . .
F1 F 0.16712(19) 0.81397(15) 1.05382(14) 0.0242(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.175(2) . ?
N1 C8 1.309(2) . ?
C3 H3 0.9500 . ?
C3 C2 1.291(3) . ?
C3 C4 1.256(3) . ?
C2 C1 1.348(2) . ?
C2 C7 1.283(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.265(3) . ?
C6 C7 1.277(3) . ?
C4 C5 1.273(3) . ?
C4 F1 1.250(2) . ?
C1 H1 0.9500 . ?
C5 F2 1.243(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.280(2) . ?
C9 C8 1.281(3) . ?
C10 H10 0.9500 . ?
C10 C8 1.288(3) 2_656 ?
C8 C10 1.288(3) 2_656 ?
C7 H7 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 C8 117.30(16) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C4 C3 C2 118.38(18) . . ?
C3 C2 C1 121.24(17) . . ?
C7 C2 C3 119.49(18) . . ?
C7 C2 C1 119.27(17) . . ?
C5 C6 H6 120.9 . . ?
C5 C6 C7 118.20(18) . . ?
C7 C6 H6 120.9 . . ?
C3 C4 C5 121.84(18) . . ?
F1 C4 C3 120.46(18) . . ?
F1 C4 C5 117.70(17) . . ?
N1 C1 C2 123.21(17) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C6 C5 C4 120.76(18) . . ?
F2 C5 C6 120.92(18) . . ?
F2 C5 C4 118.32(17) . . ?
C10 C9 H9 119.8 . . ?
C10 C9 C8 120.36(18) . . ?
C8 C9 H9 119.8 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C8 120.46(18) . 2_656 ?
C8 C10 H10 119.8 2_656 . ?
C9 C8 N1 118.12(17) . . ?
C9 C8 C10 119.15(17) . 2_656 ?
C10 C8 N1 122.72(17) 2_656 . ?
C2 C7 H7 119.3 . . ?
C6 C7 C2 121.32(18) . . ?
C6 C7 H7 119.3 . . ?

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
C3 C2 C1 N1 2.2(3) . . . . ?
C3 C2 C7 C6 -0.9(3) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C3 C4 C5 F2 179.31(16) . . . . ?
C2 C3 C4 C5 1.2(3) . . . . ?
C2 C3 C4 F1 -178.12(16) . . . . ?
C4 C3 C2 C1 178.53(16) . . . . ?
C4 C3 C2 C7 -0.4(3) . . . . ?
C1 N1 C8 C9 -139.49(18) . . . . ?
C1 N1 C8 C10 41.1(3) . . . 2_656 ?
C1 C2 C7 C6 -179.79(17) . . . . ?
C5 C6 C7 C2 1.3(3) . . . . ?
C10 C9 C8 N1 178.99(16) . . . . ?
C10 C9 C8 C10 -1.6(3) . . . 2_656 ?
C8 N1 C1 C2 -177.54(16) . . . . ?
C8 C9 C10 C8 1.6(3) . . . 2_656 ?
C7 C2 C1 N1 -178.91(18) . . . . ?
C7 C6 C5 C4 -0.5(3) . . . . ?
C7 C6 C5 F2 179.44(16) . . . . ?
F1 C4 C5 C6 178.55(17) . . . . ?
F1 C4 C5 F2 -1.4(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_15
_database_code_depnum_ccdc_archive 'CCDC 1562525'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7CE01872J 2017
_audit_update_record             
;
2017-07-17 deposited with the CCDC.
2018-01-10 downloaded from the CCDC.
;
_audit_creation_date             2017-07-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H12 F4 N2'
_chemical_formula_sum            'C20 H12 F4 N2'
_chemical_formula_weight         356.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H12 N2 F4'
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'

_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                   6.819(4)
_cell_length_b                   11.603(5)
_cell_length_c                   10.135(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.14(2)
_cell_angle_gamma                90
_cell_volume                     774.1(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3573
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      32.8900
_cell_measurement_theta_min      2.7030
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49849
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing 1995'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6538
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.528
_diffrn_reflns_theta_min         3.095
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00 105.90   0.30    8.00    --   29.89  54.00 120.00  583
  2  ω    -69.00  60.90   0.30    8.00    --   29.89  54.00 240.00  433
  3  ω    -69.00  80.70   0.30    8.00    --   29.89  54.00   0.00  499
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'Cryo loop'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0423845000
_diffrn_orient_matrix_UB_12      0.0076835000
_diffrn_orient_matrix_UB_13      -0.0711370000
_diffrn_orient_matrix_UB_21      -0.0780154000
_diffrn_orient_matrix_UB_22      -0.0394476000
_diffrn_orient_matrix_UB_23      0.0020517000
_diffrn_orient_matrix_UB_31      -0.0607054000
_diffrn_orient_matrix_UB_32      0.0456847000
_diffrn_orient_matrix_UB_33      0.0136146000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_current           12.0
_diffrn_source_power             0.6
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1474
_reflns_number_total             1762
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_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         0.340
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1762
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0434
_refine_ls_restrained_S_all      1.050
_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)+(0.0731P)²+0.1247P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1242
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.84762(13) 0.32348(7) 0.58145(8) 0.0263(3) Uani 1 1 d . . . . .
F2 F 0.94917(13) 0.37642(7) 0.84722(8) 0.0284(3) Uani 1 1 d . . . . .
N1 N 0.63390(17) 0.55892(10) 0.27961(11) 0.0200(3) Uani 1 1 d . . . . .
C1 C 0.69275(19) 0.48360(11) 0.37284(13) 0.0186(3) Uani 1 1 d . . . . .
H1 H 0.6967 0.4048 0.3481 0.022 Uiso 1 1 calc R . . . .
C2 C 0.75478(19) 0.51612(11) 0.51827(13) 0.0180(3) Uani 1 1 d . . . . .
C3 C 0.8268(2) 0.43338(11) 0.61744(13) 0.0185(3) Uani 1 1 d . . . . .
C4 C 0.87935(19) 0.46132(12) 0.75578(13) 0.0204(3) Uani 1 1 d . . . . .
C5 C 0.8610(2) 0.57180(12) 0.79892(14) 0.0223(3) Uani 1 1 d . . . . .
H5 H 0.8962 0.5902 0.8935 0.027 Uiso 1 1 calc R . . . .
C6 C 0.7897(2) 0.65621(12) 0.70076(14) 0.0229(3) Uani 1 1 d . . . . .
H6 H 0.7762 0.7333 0.7286 0.027 Uiso 1 1 calc R . . . .
C7 C 0.7378(2) 0.62896(12) 0.56195(14) 0.0207(3) Uani 1 1 d . . . . .
H7 H 0.6903 0.6879 0.4963 0.025 Uiso 1 1 calc R . . . .
C8 C 0.57123(19) 0.52495(11) 0.13996(12) 0.0180(3) Uani 1 1 d . . . . .
C9 C 0.6182(2) 0.41986(12) 0.08853(13) 0.0201(3) Uani 1 1 d . . . . .
H9 H 0.6996 0.3650 0.1481 0.024 Uiso 1 1 calc R . . . .
C10 C 0.5457(2) 0.39558(12) -0.04971(13) 0.0196(3) Uani 1 1 d . . . . .
H10 H 0.5764 0.3233 -0.0835 0.023 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C3 1.3441(16) . ?
F2 C4 1.3511(15) . ?
N1 C1 1.2727(17) . ?
N1 C8 1.4231(17) . ?
C1 H1 0.9500 . ?
C1 C2 1.4726(19) . ?
C2 C3 1.3839(19) . ?
C2 C7 1.3966(19) . ?
C3 C4 1.3917(19) . ?
C4 C5 1.371(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.3944(19) . ?
C7 H7 0.9500 . ?
C8 C9 1.3958(19) . ?
C8 C10 1.3935(19) 3_665 ?
C9 H9 0.9500 . ?
C9 C10 1.3875(19) . ?
C10 C8 1.3935(19) 3_665 ?
C10 H10 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 C8 120.18(12) . . ?
N1 C1 H1 119.3 . . ?
N1 C1 C2 121.31(13) . . ?
C2 C1 H1 119.3 . . ?
C3 C2 C1 120.25(12) . . ?
C3 C2 C7 117.60(12) . . ?
C7 C2 C1 122.12(12) . . ?
F1 C3 C2 120.24(12) . . ?
F1 C3 C4 118.47(12) . . ?
C2 C3 C4 121.28(12) . . ?
F2 C4 C3 118.24(12) . . ?
F2 C4 C5 120.55(12) . . ?
C5 C4 C3 121.21(12) . . ?
C4 C5 H5 120.8 . . ?
C4 C5 C6 118.33(12) . . ?
C6 C5 H5 120.8 . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C7 120.76(13) . . ?
C7 C6 H6 119.6 . . ?
C2 C7 H7 119.6 . . ?
C6 C7 C2 120.81(13) . . ?
C6 C7 H7 119.6 . . ?
C9 C8 N1 125.09(12) . . ?
C10 C8 N1 116.18(12) 3_665 . ?
C10 C8 C9 118.73(12) 3_665 . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 119.91(12) . . ?
C10 C9 H9 120.0 . . ?
C8 C10 H10 119.3 3_665 . ?
C9 C10 C8 121.35(13) . 3_665 ?
C9 C10 H10 119.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C3 C4 F2 0.09(18) . . . . ?
F1 C3 C4 C5 -179.84(12) . . . . ?
F2 C4 C5 C6 179.58(11) . . . . ?
N1 C1 C2 C3 -177.12(12) . . . . ?
N1 C1 C2 C7 5.0(2) . . . . ?
N1 C8 C9 C10 179.01(12) . . . . ?
C1 N1 C8 C9 -18.6(2) . . . . ?
C1 N1 C8 C10 161.44(13) . . . 3_665 ?
C1 C2 C3 F1 2.45(19) . . . . ?
C1 C2 C3 C4 -177.65(12) . . . . ?
C1 C2 C7 C6 177.25(12) . . . . ?
C2 C3 C4 F2 -179.81(11) . . . . ?
C2 C3 C4 C5 0.3(2) . . . . ?
C3 C2 C7 C6 -0.7(2) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
C4 C5 C6 C7 0.1(2) . . . . ?
C5 C6 C7 C2 0.5(2) . . . . ?
C7 C2 C3 F1 -179.55(12) . . . . ?
C7 C2 C3 C4 0.4(2) . . . . ?
C8 N1 C1 C2 -178.85(11) . . . . ?
C8 C9 C10 C8 1.1(2) . . . 3_665 ?
C10 C8 C9 C10 -1.1(2) 3_665 . . . ?

_olex2_exptl_crystal_mounting_method 'cryo loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.455
_oxdiff_exptl_absorpt_empirical_full_min 0.765
####################################################################### 
# 
# 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 1562526'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7CE01872J 2017
_audit_update_record             
;
2017-07-17 deposited with the CCDC.
2018-01-10 downloaded from the CCDC.
;
_audit_creation_date             2017-07-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H12 F4 N2'
_chemical_formula_sum            'C20 H12 F4 N2'
_chemical_formula_weight         356.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   6.846(4)
_cell_length_b                   11.633(6)
_cell_length_c                   10.202(6)
_cell_angle_alpha                90
_cell_angle_beta                 106.03(3)
_cell_angle_gamma                90
_cell_volume                     780.9(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2259
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing 1995'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5270
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         3.096
_diffrn_ambient_temperature      100.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
scan:
	Number of images: 629
	           Slice: -69.0000 - 119.7000
	     Image width: 0.3000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 240.0000
	             XTD: 49.8600
	          2theta: 29.8900
scan:
	Number of images: 600
	           Slice: -69.0000 - 111.0000
	     Image width: 0.3000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 0.0000
	             XTD: 49.8600
	          2theta: 29.8900
;
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Cryo loop'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.011037
_diffrn_orient_matrix_UB_12      0.149733
_diffrn_orient_matrix_UB_13      0.023550
_diffrn_orient_matrix_UB_21      -0.078877
_diffrn_orient_matrix_UB_22      -0.010909
_diffrn_orient_matrix_UB_23      0.032394
_diffrn_orient_matrix_UB_31      0.036276
_diffrn_orient_matrix_UB_32      0.016487
_diffrn_orient_matrix_UB_33      0.093881
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           12.0
_diffrn_source_power             0.6
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1377
_reflns_number_total             1753
_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       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1753
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0494
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0755P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1315
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C6(H6), C7(H7), C9(H9), C10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.16200(13) 0.66811(8) 0.41250(8) 0.0288(3) Uani 1 1 d . . . . .
F2 F 0.09595(13) 0.38548(8) 0.07480(8) 0.0274(3) Uani 1 1 d . . . . .
N1 N 0.36827(17) 0.43824(10) 0.72136(12) 0.0201(3) Uani 1 1 d . . . . .
C1 C 0.31035(19) 0.51248(12) 0.62594(14) 0.0184(3) Uani 1 1 d . . . . .
H1 H 0.3084 0.5917 0.6482 0.022 Uiso 1 1 calc R . . . .
C2 C 0.24692(19) 0.47669(12) 0.48252(14) 0.0177(3) Uani 1 1 d . . . . .
C3 C 0.1770(2) 0.55681(12) 0.37819(15) 0.0195(3) Uani 1 1 d . . . . .
C4 C 0.12314(19) 0.52901(13) 0.24075(13) 0.0201(3) Uani 1 1 d . . . . .
H4 H 0.0750 0.5855 0.1722 0.024 Uiso 1 1 calc R . . . .
C5 C 0.1429(2) 0.41574(13) 0.20870(14) 0.0211(3) Uani 1 1 d . . . . .
C6 C 0.2087(2) 0.33082(13) 0.30546(14) 0.0227(3) Uani 1 1 d . . . . .
H6 H 0.2188 0.2531 0.2795 0.027 Uiso 1 1 calc R . . . .
C7 C 0.2596(2) 0.36266(13) 0.44242(14) 0.0215(3) Uani 1 1 d . . . . .
H7 H 0.3042 0.3053 0.5104 0.026 Uiso 1 1 calc R . . . .
C8 C 0.43099(19) 0.47387(12) 0.86000(14) 0.0175(3) Uani 1 1 d . . . . .
C9 C 0.3780(2) 0.57793(12) 0.90987(14) 0.0197(3) Uani 1 1 d . . . . .
H9 H 0.2940 0.6313 0.8491 0.024 Uiso 1 1 calc R . . . .
C10 C 0.5523(2) 0.39654(12) 0.95210(14) 0.0194(3) Uani 1 1 d . . . . .
H10 H 0.5877 0.3251 0.9197 0.023 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C3 1.3525(18) . ?
F2 C5 1.3604(17) . ?
N1 C1 1.280(2) . ?
N1 C8 1.4217(19) . ?
C1 H1 0.9500 . ?
C1 C2 1.467(2) . ?
C2 C3 1.396(2) . ?
C2 C7 1.398(2) . ?
C3 C4 1.386(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.373(2) . ?
C5 C6 1.381(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.394(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.399(2) . ?
C8 C10 1.397(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.388(2) 3_667 ?
C10 C9 1.388(2) 3_667 ?
C10 H10 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 C8 120.33(13) . . ?
N1 C1 H1 119.6 . . ?
N1 C1 C2 120.76(14) . . ?
C2 C1 H1 119.6 . . ?
C3 C2 C1 121.04(13) . . ?
C3 C2 C7 116.50(13) . . ?
C7 C2 C1 122.42(13) . . ?
F1 C3 C2 118.44(13) . . ?
F1 C3 C4 117.85(13) . . ?
C4 C3 C2 123.71(14) . . ?
C3 C4 H4 121.7 . . ?
C5 C4 C3 116.65(13) . . ?
C5 C4 H4 121.7 . . ?
F2 C5 C4 118.42(13) . . ?
F2 C5 C6 118.20(14) . . ?
C4 C5 C6 123.38(13) . . ?
C5 C6 H6 121.0 . . ?
C5 C6 C7 117.93(14) . . ?
C7 C6 H6 121.0 . . ?
C2 C7 H7 119.1 . . ?
C6 C7 C2 121.81(14) . . ?
C6 C7 H7 119.1 . . ?
C9 C8 N1 125.21(13) . . ?
C10 C8 N1 116.21(13) . . ?
C10 C8 C9 118.57(13) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.18(14) 3_667 . ?
C10 C9 H9 119.9 3_667 . ?
C8 C10 H10 119.4 . . ?
C9 C10 C8 121.24(14) 3_667 . ?
C9 C10 H10 119.4 3_667 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C3 C4 C5 178.99(11) . . . . ?
F2 C5 C6 C7 178.99(11) . . . . ?
N1 C1 C2 C3 177.80(12) . . . . ?
N1 C1 C2 C7 -4.6(2) . . . . ?
N1 C8 C9 C10 179.73(11) . . . 3_667 ?
N1 C8 C10 C9 -179.84(11) . . . 3_667 ?
C1 N1 C8 C9 21.65(19) . . . . ?
C1 N1 C8 C10 -159.47(12) . . . . ?
C1 C2 C3 F1 -2.34(19) . . . . ?
C1 C2 C3 C4 177.17(12) . . . . ?
C1 C2 C7 C6 -176.65(12) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C3 C2 C7 C6 1.1(2) . . . . ?
C3 C4 C5 F2 -178.52(10) . . . . ?
C3 C4 C5 C6 1.3(2) . . . . ?
C4 C5 C6 C7 -0.8(2) . . . . ?
C5 C6 C7 C2 -0.5(2) . . . . ?
C7 C2 C3 F1 179.88(11) . . . . ?
C7 C2 C3 C4 -0.6(2) . . . . ?
C8 N1 C1 C2 179.50(11) . . . . ?
C9 C8 C10 C9 -0.9(2) . . . 3_667 ?
C10 C8 C9 C10 0.9(2) . . . 3_667 ?

_olex2_exptl_crystal_mounting_method 'cryo loop'
_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_18
_database_code_depnum_ccdc_archive 'CCDC 1562528'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7CE01872J 2017
_audit_update_record             
;
2017-07-17 deposited with the CCDC.
2018-01-10 downloaded from the CCDC.
;
_audit_creation_date             2017-07-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H12 F4 N2'
_chemical_formula_sum            'C20 H12 F4 N2'
_chemical_formula_weight         356.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   4.837(7)
_cell_length_b                   18.14(2)
_cell_length_c                   8.981(14)
_cell_angle_alpha                90
_cell_angle_beta                 93.42(7)
_cell_angle_gamma                90
_cell_volume                     786.7(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1669
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.2
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessings, 1995'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Prism
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7770
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         3.195
_diffrn_ambient_temperature      100.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
scan:
	Number of images: 600
	           Slice: -69.0000 - 111.0000
	     Image width: 0.3000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 0.0000
	             XTD: 49.8600
	          2theta: 29.8900
scan:
	Number of images: 600
	           Slice: -69.0000 - 111.0000
	     Image width: 0.3000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 240.0000
	             XTD: 49.8600
	          2theta: 29.8900
scan:
	Number of images: 600
	           Slice: -69.0000 - 111.0000
	     Image width: 0.3000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 120.0000
	             XTD: 49.8600
	          2theta: 29.8900
;
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Cryo loop'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.189752
_diffrn_orient_matrix_UB_12      0.030547
_diffrn_orient_matrix_UB_13      -0.077204
_diffrn_orient_matrix_UB_21      -0.013688
_diffrn_orient_matrix_UB_22      -0.028726
_diffrn_orient_matrix_UB_23      -0.045009
_diffrn_orient_matrix_UB_31      -0.028936
_diffrn_orient_matrix_UB_32      0.094583
_diffrn_orient_matrix_UB_33      -0.051565
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           12.0
_diffrn_source_power             0.6
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1281
_reflns_number_total             1772
_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       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_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         0.316
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1772
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0430
_refine_ls_restrained_S_all      0.980
_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)+(0.0696P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1275
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C5(H5), C4(H4), C6(H6), C1(H1), C9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F2 F 0.33199(19) 0.24671(5) 0.73914(10) 0.0246(3) Uani 1 1 d . . . . .
F1 F 0.7828(2) 0.44850(5) 0.52698(11) 0.0297(3) Uani 1 1 d . . . . .
N1 N 0.2519(3) 0.38901(7) 0.83496(14) 0.0219(3) Uani 1 1 d . . . . .
C3 C 0.7441(4) 0.37474(9) 0.54214(17) 0.0216(4) Uani 1 1 d . . . . .
C10 C 0.0892(4) 0.43441(9) 1.06538(18) 0.0232(4) Uani 1 1 d . . . . .
H10 H 0.1491 0.3893 1.1104 0.028 Uiso 1 1 calc R . . . .
C5 C 0.8568(3) 0.25298(9) 0.47179(17) 0.0231(4) Uani 1 1 d . . . . .
H5 H 0.9615 0.2196 0.4162 0.028 Uiso 1 1 calc R . . . .
C4 C 0.8965(3) 0.32825(9) 0.45711(16) 0.0233(4) Uani 1 1 d . . . . .
H4 H 1.0245 0.3472 0.3906 0.028 Uiso 1 1 calc R . . . .
C6 C 0.6660(4) 0.22623(9) 0.56682(17) 0.0222(4) Uani 1 1 d . . . . .
H6 H 0.6374 0.1747 0.5757 0.027 Uiso 1 1 calc R . . . .
C7 C 0.5175(3) 0.27500(9) 0.64864(16) 0.0195(4) Uani 1 1 d . . . . .
C1 C 0.4128(3) 0.40617(9) 0.73309(17) 0.0213(4) Uani 1 1 d . . . . .
H1 H 0.4449 0.4569 0.7148 0.026 Uiso 1 1 calc R . . . .
C9 C 0.0358(3) 0.51263(9) 0.84937(17) 0.0225(4) Uani 1 1 d . . . . .
H9 H 0.0587 0.5214 0.7465 0.027 Uiso 1 1 calc R . . . .
C2 C 0.5512(3) 0.35155(8) 0.64248(16) 0.0200(4) Uani 1 1 d . . . . .
C8 C 0.1279(3) 0.44651(8) 0.91488(17) 0.0205(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F2 C7 1.348(2) . ?
F1 C3 1.359(2) . ?
N1 C1 1.275(2) . ?
N1 C8 1.419(2) . ?
C3 C4 1.380(3) . ?
C3 C2 1.400(3) . ?
C10 H10 0.9500 . ?
C10 C9 1.389(3) 3_567 ?
C10 C8 1.393(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.386(3) . ?
C5 C6 1.382(3) . ?
C4 H4 0.9500 . ?
C6 H6 0.9500 . ?
C6 C7 1.379(3) . ?
C7 C2 1.400(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.469(2) . ?
C9 C10 1.389(3) 3_567 ?
C9 H9 0.9500 . ?
C9 C8 1.397(3) . ?

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 C8 118.55(15) . . ?
F1 C3 C4 117.71(15) . . ?
F1 C3 C2 117.48(14) . . ?
C4 C3 C2 124.82(17) . . ?
C9 C10 H10 119.5 3_567 . ?
C9 C10 C8 120.92(16) 3_567 . ?
C8 C10 H10 119.5 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C6 C5 C4 120.39(14) . . ?
C3 C4 C5 117.89(16) . . ?
C3 C4 H4 121.1 . . ?
C5 C4 H4 121.1 . . ?
C5 C6 H6 120.3 . . ?
C7 C6 C5 119.48(17) . . ?
C7 C6 H6 120.3 . . ?
F2 C7 C6 117.64(16) . . ?
F2 C7 C2 119.00(14) . . ?
C6 C7 C2 123.36(16) . . ?
N1 C1 H1 118.3 . . ?
N1 C1 C2 123.43(16) . . ?
C2 C1 H1 118.3 . . ?
C10 C9 H9 120.0 3_567 . ?
C10 C9 C8 120.00(17) 3_567 . ?
C8 C9 H9 120.0 . . ?
C3 C2 C1 119.81(16) . . ?
C7 C2 C3 114.03(14) . . ?
C7 C2 C1 126.13(15) . . ?
C10 C8 N1 117.40(15) . . ?
C10 C8 C9 119.07(15) . . ?
C9 C8 N1 123.49(16) . . ?

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
F2 C7 C2 C3 -178.50(13) . . . . ?
F2 C7 C2 C1 3.7(2) . . . . ?
F1 C3 C4 C5 -179.74(13) . . . . ?
F1 C3 C2 C7 178.29(13) . . . . ?
F1 C3 C2 C1 -3.8(2) . . . . ?
N1 C1 C2 C3 -174.24(15) . . . . ?
N1 C1 C2 C7 3.4(3) . . . . ?
C10 C9 C8 N1 178.54(16) 3_567 . . . ?
C10 C9 C8 C10 0.8(3) 3_567 . . . ?
C5 C6 C7 F2 179.51(13) . . . . ?
C5 C6 C7 C2 -0.8(2) . . . . ?
C4 C3 C2 C7 -1.3(2) . . . . ?
C4 C3 C2 C1 176.57(15) . . . . ?
C4 C5 C6 C7 -0.8(2) . . . . ?
C6 C5 C4 C3 1.3(2) . . . . ?
C6 C7 C2 C3 1.8(2) . . . . ?
C6 C7 C2 C1 -175.98(15) . . . . ?
C1 N1 C8 C10 -144.92(16) . . . . ?
C1 N1 C8 C9 37.3(2) . . . . ?
C9 C10 C8 N1 -178.69(16) 3_567 . . . ?
C9 C10 C8 C9 -0.8(3) 3_567 . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C8 N1 C1 C2 -179.58(14) . . . . ?

_olex2_exptl_crystal_mounting_method 'cryo loop'
_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_2
_database_code_depnum_ccdc_archive 'CCDC 1562530'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7CE01872J 2017
_audit_update_record             
;
2017-07-17 deposited with the CCDC.
2018-01-10 downloaded from the CCDC.
;
_audit_creation_date             2017-07-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 F2 N2'
_chemical_formula_sum            'C20 H14 F2 N2'
_chemical_formula_weight         318.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   5.775(4)
_cell_length_b                   20.795(7)
_cell_length_c                   6.653(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.46(2)
_cell_angle_gamma                90
_cell_volume                     762.2(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1905
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.2
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.637
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing 1995'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_unetI/netI     0.0938
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5422
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         3.356
_diffrn_ambient_temperature      100.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
scan:
	Number of images: 629
	           Slice: -69.0000 - 119.7000
	     Image width: 0.3000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 240.0000
	             XTD: 49.8600
	          2theta: 29.8900
scan:
	Number of images: 629
	           Slice: -69.0000 - 119.7000
	     Image width: 0.3000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 120.0000
	             XTD: 49.8600
	          2theta: 29.8900
;
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'Cryo loop'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.032681
_diffrn_orient_matrix_UB_12      -0.046834
_diffrn_orient_matrix_UB_13      0.172311
_diffrn_orient_matrix_UB_21      0.004268
_diffrn_orient_matrix_UB_22      0.046010
_diffrn_orient_matrix_UB_23      0.013315
_diffrn_orient_matrix_UB_31      -0.155756
_diffrn_orient_matrix_UB_32      0.007954
_diffrn_orient_matrix_UB_33      0.022437
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           12.0
_diffrn_source_power             0.6
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                951
_reflns_number_total             1739
_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       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_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         0.290
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.902
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1739
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0441
_refine_ls_restrained_S_all      0.902
_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)+(0.0374P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.1160
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C1(H1), C7(H7), C4(H4), C10(H10), C5(H5), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.2888(2) 0.32722(6) 0.46382(18) 0.0319(4) Uani 1 1 d . . . . .
N1 N 0.6617(3) 0.40968(8) 0.5275(3) 0.0217(4) Uani 1 1 d . . . . .
C8 C 0.9419(3) 0.46211(9) 0.8184(3) 0.0185(4) Uani 1 1 d . . . . .
C9 C 1.1764(4) 0.46160(9) 0.9582(3) 0.0213(5) Uani 1 1 d . . . . .
H9 H 1.2973 0.4354 0.9294 0.026 Uiso 1 1 calc R . . . .
C3 C 0.4065(4) 0.32874(10) 0.3150(3) 0.0215(5) Uani 1 1 d . . . . .
C1 C 0.8815(4) 0.41989(9) 0.6342(3) 0.0217(5) Uani 1 1 d . . . . .
H1 H 1.0083 0.3998 0.5935 0.026 Uiso 1 1 calc R . . . .
C2 C 0.6069(3) 0.36906(9) 0.3500(3) 0.0202(5) Uani 1 1 d . . . . .
C7 C 0.7280(4) 0.36910(9) 0.1972(3) 0.0228(5) Uani 1 1 d . . . . .
H7 H 0.8666 0.3957 0.2153 0.027 Uiso 1 1 calc R . . . .
C4 C 0.3250(4) 0.29011(10) 0.1407(3) 0.0236(5) Uani 1 1 d . . . . .
H4 H 0.1881 0.2630 0.1234 0.028 Uiso 1 1 calc R . . . .
C10 C 0.7653(3) 0.50098(9) 0.8612(3) 0.0211(5) Uani 1 1 d . . . . .
H10 H 0.6052 0.5018 0.7665 0.025 Uiso 1 1 calc R . . . .
C5 C 0.4469(4) 0.29168(10) -0.0088(3) 0.0262(5) Uani 1 1 d . . . . .
H5 H 0.3927 0.2658 -0.1317 0.031 Uiso 1 1 calc R . . . .
C6 C 0.6483(4) 0.33092(10) 0.0201(3) 0.0241(5) Uani 1 1 d . . . . .
H6 H 0.7321 0.3315 -0.0829 0.029 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C3 1.359(2) . ?
N1 C1 1.273(3) . ?
N1 C2 1.409(2) . ?
C8 C9 1.394(3) . ?
C8 C1 1.462(3) . ?
C8 C10 1.396(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(3) 3_767 ?
C3 C2 1.391(3) . ?
C3 C4 1.372(3) . ?
C1 H1 0.9500 . ?
C2 C7 1.396(3) . ?
C7 H7 0.9500 . ?
C7 C6 1.380(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.381(3) . ?
C10 C9 1.386(3) 3_767 ?
C10 H10 0.9500 . ?
C5 H5 0.9500 . ?
C5 C6 1.386(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 C2 120.18(18) . . ?
C9 C8 C1 119.65(18) . . ?
C9 C8 C10 119.40(17) . . ?
C10 C8 C1 120.90(18) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.61(18) 3_767 . ?
C10 C9 H9 119.7 3_767 . ?
F1 C3 C2 117.70(18) . . ?
F1 C3 C4 118.83(18) . . ?
C4 C3 C2 123.45(19) . . ?
N1 C1 C8 120.98(19) . . ?
N1 C1 H1 119.5 . . ?
C8 C1 H1 119.5 . . ?
C3 C2 N1 117.88(18) . . ?
C3 C2 C7 116.87(18) . . ?
C7 C2 N1 125.09(19) . . ?
C2 C7 H7 119.7 . . ?
C6 C7 C2 120.63(19) . . ?
C6 C7 H7 119.7 . . ?
C3 C4 H4 120.8 . . ?
C3 C4 C5 118.4(2) . . ?
C5 C4 H4 120.8 . . ?
C8 C10 H10 120.0 . . ?
C9 C10 C8 119.99(18) 3_767 . ?
C9 C10 H10 120.0 3_767 . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.1(2) . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 120.5(2) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C3 C2 N1 -5.4(3) . . . . ?
F1 C3 C2 C7 178.88(16) . . . . ?
F1 C3 C4 C5 -179.53(17) . . . . ?
N1 C2 C7 C6 -174.83(18) . . . . ?
C9 C8 C1 N1 165.99(18) . . . . ?
C9 C8 C10 C9 -0.3(3) . . . 3_767 ?
C3 C2 C7 C6 0.5(3) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C1 N1 C2 C3 141.7(2) . . . . ?
C1 N1 C2 C7 -43.0(3) . . . . ?
C1 C8 C9 C10 -177.03(18) . . . 3_767 ?
C1 C8 C10 C9 176.99(18) . . . 3_767 ?
C2 N1 C1 C8 179.73(17) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C2 C7 C6 C5 -0.2(3) . . . . ?
C4 C3 C2 N1 175.58(18) . . . . ?
C4 C3 C2 C7 -0.1(3) . . . . ?
C4 C5 C6 C7 -0.5(3) . . . . ?
C10 C8 C9 C10 0.3(3) . . . 3_767 ?
C10 C8 C1 N1 -11.3(3) . . . . ?

_olex2_exptl_crystal_mounting_method 'Cryo loop'
_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_9
_database_code_depnum_ccdc_archive 'CCDC 1562538'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7CE01872J 2017
_audit_update_record             
;
2017-07-17 deposited with the CCDC.
2018-01-10 downloaded from the CCDC.
;
_audit_creation_date             2017-06-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H12 F4 N2'
_chemical_formula_sum            'C20 H12 F4 N2'
_chemical_formula_weight         356.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   4.6210(4)
_cell_length_b                   14.8580(14)
_cell_length_c                   11.0496(9)
_cell_angle_alpha                90
_cell_angle_beta                 94.614(8)
_cell_angle_gamma                90
_cell_volume                     756.19(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2889
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      32.3800
_cell_measurement_theta_min      2.3380
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.7f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10707
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         32.791
_diffrn_reflns_theta_min         2.302
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -68.70 119.70   0.30   20.00    --   29.89  54.00 240.00  628
  2  ω    -68.70 119.70   0.30   20.00    --   29.89  54.00 120.00  628
  3  ω    -69.00 119.70   0.30   20.00    --   29.89  54.00   0.00  629
;
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0125813000
_diffrn_orient_matrix_UB_12      -0.0456197000
_diffrn_orient_matrix_UB_13      0.0177531000
_diffrn_orient_matrix_UB_21      -0.1509329000
_diffrn_orient_matrix_UB_22      0.0061187000
_diffrn_orient_matrix_UB_23      0.0044807000
_diffrn_orient_matrix_UB_31      -0.0276240000
_diffrn_orient_matrix_UB_32      -0.0126493000
_diffrn_orient_matrix_UB_33      -0.0617714000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1823
_reflns_number_total             2707
_reflns_odcompleteness_completeness 96.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.72
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.794
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2707
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1031
_refine_ls_R_factor_gt           0.0727
_refine_ls_restrained_S_all      1.063
_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)+(0.1209P)²+0.1894P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1846
_refine_ls_wR_factor_ref         0.2237
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C10(H10), C6(H6), C1(H1), C7(H7), C9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.1655(3) 0.91740(8) 0.35928(10) 0.0323(3) Uani 1 1 d . . . . .
C3 C -0.1535(3) 0.80518(11) 0.42311(14) 0.0195(3) Uani 1 1 d . . . . .
H3 H -0.2217 0.7947 0.3429 0.023 Uiso 1 1 calc R . . . .
C10 C -0.8986(3) 0.51735(11) 0.61927(14) 0.0191(3) Uani 1 1 d . . . . .
H10 H -0.8300 0.5289 0.6992 0.023 Uiso 1 1 calc R . . . .
N1 N -0.4761(3) 0.69009(9) 0.47868(12) 0.0189(3) Uani 1 1 d . . . . .
F2 F 0.3628(2) 0.95150(7) 0.59206(9) 0.0260(3) Uani 1 1 d . . . . .
C6 C 0.0495(3) 0.84008(11) 0.66268(14) 0.0188(3) Uani 1 1 d . . . . .
H6 H 0.1160 0.8521 0.7427 0.023 Uiso 1 1 calc R . . . .
C8 C -0.7921(3) 0.56802(10) 0.52543(14) 0.0161(3) Uani 1 1 d . . . . .
C1 C -0.5752(3) 0.63727(11) 0.55686(14) 0.0184(3) Uani 1 1 d . . . . .
H1 H -0.5054 0.6433 0.6378 0.022 Uiso 1 1 calc R . . . .
C2 C -0.2628(3) 0.75538(11) 0.51644(14) 0.0176(3) Uani 1 1 d . . . . .
C5 C 0.1589(3) 0.88773(11) 0.56894(15) 0.0194(3) Uani 1 1 d . . . . .
C7 C -0.1598(3) 0.77433(12) 0.63698(15) 0.0209(4) Uani 1 1 d . . . . .
H7 H -0.2328 0.7424 0.7002 0.025 Uiso 1 1 calc R . . . .
C9 C -0.8958(4) 0.54959(11) 0.40476(14) 0.0192(3) Uani 1 1 d . . . . .
H9 H -0.8266 0.5822 0.3413 0.023 Uiso 1 1 calc R . . . .
C4 C 0.0568(4) 0.87031(12) 0.45017(14) 0.0205(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C4 1.3533(19) . ?
C3 H3 0.9300 . ?
C3 C2 1.396(2) . ?
C3 C4 1.387(2) . ?
C10 H10 0.9300 . ?
C10 C8 1.402(2) . ?
C10 C9 1.386(2) 3_366 ?
N1 C1 1.279(2) . ?
N1 C2 1.422(2) . ?
F2 C5 1.3461(18) . ?
C6 H6 0.9300 . ?
C6 C5 1.383(2) . ?
C6 C7 1.388(2) . ?
C8 C1 1.459(2) . ?
C8 C9 1.407(2) . ?
C1 H1 0.9300 . ?
C2 C7 1.406(2) . ?
C5 C4 1.383(2) . ?
C7 H7 0.9300 . ?
C9 C10 1.386(2) 3_366 ?
C9 H9 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C4 C3 C2 119.96(14) . . ?
C8 C10 H10 119.4 . . ?
C9 C10 H10 119.4 3_366 . ?
C9 C10 C8 121.30(14) 3_366 . ?
C1 N1 C2 119.87(14) . . ?
C5 C6 H6 120.1 . . ?
C5 C6 C7 119.84(14) . . ?
C7 C6 H6 120.1 . . ?
C10 C8 C1 118.55(14) . . ?
C10 C8 C9 118.90(14) . . ?
C9 C8 C1 122.55(14) . . ?
N1 C1 C8 123.26(14) . . ?
N1 C1 H1 118.4 . . ?
C8 C1 H1 118.4 . . ?
C3 C2 N1 115.37(14) . . ?
C3 C2 C7 118.58(14) . . ?
C7 C2 N1 126.05(14) . . ?
F2 C5 C6 120.69(14) . . ?
F2 C5 C4 119.47(15) . . ?
C4 C5 C6 119.84(15) . . ?
C6 C7 C2 120.79(15) . . ?
C6 C7 H7 119.6 . . ?
C2 C7 H7 119.6 . . ?
C10 C9 C8 119.80(15) 3_366 . ?
C10 C9 H9 120.1 3_366 . ?
C8 C9 H9 120.1 . . ?
F1 C4 C3 119.74(14) . . ?
F1 C4 C5 119.28(15) . . ?
C5 C4 C3 120.98(15) . . ?

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
C3 C2 C7 C6 -1.0(2) . . . . ?
C10 C8 C1 N1 -176.21(15) . . . . ?
C10 C8 C9 C10 0.5(3) . . . 3_366 ?
N1 C2 C7 C6 -179.86(15) . . . . ?
F2 C5 C4 F1 0.4(2) . . . . ?
F2 C5 C4 C3 -179.89(15) . . . . ?
C6 C5 C4 F1 179.98(15) . . . . ?
C6 C5 C4 C3 -0.3(3) . . . . ?
C1 N1 C2 C3 175.47(15) . . . . ?
C1 N1 C2 C7 -5.7(3) . . . . ?
C1 C8 C9 C10 179.74(15) . . . 3_366 ?
C2 C3 C4 F1 178.94(15) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C2 N1 C1 C8 -179.45(14) . . . . ?
C5 C6 C7 C2 0.0(3) . . . . ?
C7 C6 C5 F2 -179.74(14) . . . . ?
C7 C6 C5 C4 0.7(3) . . . . ?
C9 C10 C8 C1 -179.78(15) 3_366 . . . ?
C9 C10 C8 C9 -0.5(3) 3_366 . . . ?
C9 C8 C1 N1 4.5(3) . . . . ?
C4 C3 C2 N1 -179.65(15) . . . . ?
C4 C3 C2 C7 1.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.338
_oxdiff_exptl_absorpt_empirical_full_min 0.864
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1562532'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7CE01872J 2017
_audit_update_record             
;
2017-07-17 deposited with the CCDC.
2018-01-10 downloaded from the CCDC.
;
_audit_creation_date             2017-07-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 F2 N2'
_chemical_formula_sum            'C20 H14 F2 N2'
_chemical_formula_weight         320.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.445(3)
_cell_length_b                   3.9293(14)
_cell_length_c                   20.333(8)
_cell_angle_alpha                90
_cell_angle_beta                 93.987(16)
_cell_angle_gamma                90
_cell_volume                     752.7(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1752
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      2.0
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.780
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessings, 1995'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_av_unetI/netI     0.0904
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            4755
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.506
_diffrn_reflns_theta_min         3.585
_diffrn_ambient_temperature      100.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details      
;
scan:
	Number of images: 629
	           Slice: -69.0000 - 119.7000
	     Image width: 0.3000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 240.0000
	             XTD: 49.8600
	          2theta: 29.8900
scan:
	Number of images: 583
	           Slice: -69.0000 - 105.9000
	     Image width: 0.3000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 120.0000
	             XTD: 49.8600
	          2theta: 29.8900
scan:
	Number of images: 434
	           Slice: -37.0000 - 93.2000
	     Image width: 0.3000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 0.0000
	             XTD: 49.8600
	          2theta: 29.8900
;
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Cryo loop'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.086619
_diffrn_orient_matrix_UB_12      -0.002890
_diffrn_orient_matrix_UB_13      -0.061265
_diffrn_orient_matrix_UB_21      -0.127666
_diffrn_orient_matrix_UB_22      0.134699
_diffrn_orient_matrix_UB_23      0.174146
_diffrn_orient_matrix_UB_31      0.011312
_diffrn_orient_matrix_UB_32      0.041614
_diffrn_orient_matrix_UB_33      -0.023895
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           12.0
_diffrn_source_power             0.6
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1042
_reflns_number_total             1651
_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       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1651
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1231
_refine_ls_R_factor_gt           0.0860
_refine_ls_restrained_S_all      1.066
_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)+(0.1287P)²+0.1091P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2242
_refine_ls_wR_factor_ref         0.2483
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C1(H1), C6(H6), C5(H5), C3(H3), C7(H7), C10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.4570(2) 0.7932(5) 0.20129(10) 0.0350(7) Uani 1 1 d . . . . .
N1 N 0.3348(3) 0.7411(7) 0.42622(13) 0.0224(7) Uani 1 1 d . . . . .
C9 C 0.1453(3) 0.4481(8) 0.51566(16) 0.0211(7) Uani 1 1 d . . . . .
H9 H 0.2436 0.4115 0.5263 0.025 Uiso 1 1 calc R . . . .
C8 C 0.1002(3) 0.6212(8) 0.45824(16) 0.0200(7) Uani 1 1 d . . . . .
C1 C 0.2005(3) 0.7534(8) 0.41293(16) 0.0211(8) Uani 1 1 d . . . . .
H1 H 0.1649 0.8514 0.3724 0.025 Uiso 1 1 calc R . . . .
C6 C 0.6375(4) 1.1324(9) 0.34985(17) 0.0254(8) Uani 1 1 d . . . . .
H6 H 0.7210 1.2566 0.3630 0.030 Uiso 1 1 calc R . . . .
C2 C 0.4218(3) 0.8519(8) 0.37691(16) 0.0209(8) Uani 1 1 d . . . . .
C5 C 0.6075(3) 1.0553(9) 0.28295(17) 0.0248(8) Uani 1 1 d . . . . .
H5 H 0.6694 1.1243 0.2506 0.030 Uiso 1 1 calc R . . . .
C3 C 0.3918(3) 0.7714(8) 0.31048(17) 0.0231(8) Uani 1 1 d . . . . .
H3 H 0.3088 0.6474 0.2965 0.028 Uiso 1 1 calc R . . . .
C7 C 0.5476(3) 1.0307(8) 0.39681(17) 0.0236(8) Uani 1 1 d . . . . .
H7 H 0.5700 1.0803 0.4421 0.028 Uiso 1 1 calc R . . . .
C10 C 0.0459(4) 0.3288(8) 0.55745(17) 0.0223(8) Uani 1 1 d . . . . .
H10 H 0.0768 0.2128 0.5969 0.027 Uiso 1 1 calc R . . . .
C4 C 0.4855(4) 0.8765(8) 0.26602(16) 0.0237(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C4 1.365(4) . ?
N1 C1 1.279(4) . ?
N1 C2 1.409(4) . ?
C9 H9 0.9500 . ?
C9 C8 1.392(4) . ?
C9 C10 1.390(5) . ?
C8 C1 1.462(5) . ?
C8 C10 1.409(5) 3_566 ?
C1 H1 0.9500 . ?
C6 H6 0.9500 . ?
C6 C5 1.403(5) . ?
C6 C7 1.380(5) . ?
C2 C3 1.397(5) . ?
C2 C7 1.415(5) . ?
C5 H5 0.9500 . ?
C5 C4 1.373(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.372(5) . ?
C7 H7 0.9500 . ?
C10 C8 1.409(5) 3_566 ?
C10 H10 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 C2 117.2(3) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C10 C9 C8 119.8(3) . . ?
C9 C8 C1 121.9(3) . . ?
C9 C8 C10 119.7(3) . 3_566 ?
C10 C8 C1 118.4(3) 3_566 . ?
N1 C1 C8 122.0(3) . . ?
N1 C1 H1 119.0 . . ?
C8 C1 H1 119.0 . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C7 C6 C5 121.1(3) . . ?
N1 C2 C7 118.0(3) . . ?
C3 C2 N1 121.9(3) . . ?
C3 C2 C7 119.9(3) . . ?
C6 C5 H5 121.2 . . ?
C4 C5 C6 117.5(3) . . ?
C4 C5 H5 121.2 . . ?
C2 C3 H3 120.9 . . ?
C4 C3 C2 118.2(3) . . ?
C4 C3 H3 120.9 . . ?
C6 C7 C2 119.4(3) . . ?
C6 C7 H7 120.3 . . ?
C2 C7 H7 120.3 . . ?
C9 C10 C8 120.5(3) . 3_566 ?
C9 C10 H10 119.8 . . ?
C8 C10 H10 119.8 3_566 . ?
F1 C4 C5 118.1(3) . . ?
F1 C4 C3 118.0(3) . . ?
C3 C4 C5 123.9(3) . . ?

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 C2 C3 C4 -177.1(3) . . . . ?
N1 C2 C7 C6 177.8(3) . . . . ?
C9 C8 C1 N1 -5.7(5) . . . . ?
C8 C9 C10 C8 0.7(5) . . . 3_566 ?
C1 N1 C2 C3 -41.1(4) . . . . ?
C1 N1 C2 C7 143.0(3) . . . . ?
C6 C5 C4 F1 -178.5(3) . . . . ?
C6 C5 C4 C3 0.3(5) . . . . ?
C2 N1 C1 C8 175.2(3) . . . . ?
C2 C3 C4 F1 179.0(3) . . . . ?
C2 C3 C4 C5 0.2(5) . . . . ?
C5 C6 C7 C2 -1.3(5) . . . . ?
C3 C2 C7 C6 1.8(5) . . . . ?
C7 C6 C5 C4 0.2(5) . . . . ?
C7 C2 C3 C4 -1.3(5) . . . . ?
C10 C9 C8 C1 179.6(3) . . . . ?
C10 C9 C8 C10 -0.7(5) . . . 3_566 ?
C10 C8 C1 N1 174.5(3) 3_566 . . . ?

_olex2_exptl_crystal_mounting_method 'Cryo loop'
_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_8
_database_code_depnum_ccdc_archive 'CCDC 1562537'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7CE01872J 2017
_audit_update_record             
;
2017-07-17 deposited with the CCDC.
2018-01-10 downloaded from the CCDC.
;
_audit_creation_date             2017-07-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H12 F4 N2'
_chemical_formula_sum            'C20 H12 F4 N2'
_chemical_formula_weight         356.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   15.229(16)
_cell_length_b                   3.914(3)
_cell_length_c                   13.287(11)
_cell_angle_alpha                90
_cell_angle_beta                 102.54(4)
_cell_angle_gamma                90
_cell_volume                     773.2(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1977
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessings, 1995'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0927
_diffrn_reflns_av_unetI/netI     0.0694
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7387
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.469
_diffrn_reflns_theta_min         3.141
_diffrn_ambient_temperature      100.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
scan:
	Number of images: 629
	           Slice: -69.0000 - 119.7000
	     Image width: 0.3000
	        Exp time: 12.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 0.0000
	             XTD: 49.8600
	          2theta: 29.8900
scan:
	Number of images: 629
	           Slice: -69.0000 - 119.7000
	     Image width: 0.3000
	        Exp time: 12.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 120.0000
	             XTD: 49.8600
	          2theta: 29.8900
scan:
	Number of images: 629
	           Slice: -69.0000 - 119.7000
	     Image width: 0.3000
	        Exp time: 12.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 240.0000
	             XTD: 49.8600
	          2theta: 29.8900
;
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Cryo loop'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.027827
_diffrn_orient_matrix_UB_12      0.070917
_diffrn_orient_matrix_UB_13      -0.011860
_diffrn_orient_matrix_UB_21      -0.027619
_diffrn_orient_matrix_UB_22      -0.031311
_diffrn_orient_matrix_UB_23      -0.252032
_diffrn_orient_matrix_UB_31      -0.055553
_diffrn_orient_matrix_UB_32      0.037906
_diffrn_orient_matrix_UB_33      0.001379
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           12.0
_diffrn_source_power             0.6
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1059
_reflns_number_total             1733
_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       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_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         0.834
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1733
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1270
_refine_ls_R_factor_gt           0.0911
_refine_ls_restrained_S_all      1.069
_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)+(0.1788P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2369
_refine_ls_wR_factor_ref         0.2914
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C1(H1), C9(H9), C10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.69386(12) 0.6015(5) 0.21691(15) 0.0415(6) Uani 1 1 d . . . . .
F2 F 0.86900(13) 1.0845(5) 0.51843(15) 0.0431(6) Uani 1 1 d . . . . .
N1 N 0.71792(16) 0.7200(7) 0.4308(2) 0.0353(7) Uani 1 1 d . . . . .
C2 C 0.7761(2) 0.8496(8) 0.3698(2) 0.0335(8) Uani 1 1 d . . . . .
C3 C 0.7657(2) 0.7912(9) 0.2647(3) 0.0368(8) Uani 1 1 d . . . . .
C4 C 0.8249(2) 0.9054(8) 0.2066(3) 0.0368(8) Uani 1 1 d . . . . .
H4 H 0.8142 0.8629 0.1345 0.044 Uiso 1 1 calc R . . . .
C5 C 0.9001(2) 1.0834(8) 0.2568(3) 0.0385(9) Uani 1 1 d . . . . .
H5 H 0.9418 1.1648 0.2186 0.046 Uiso 1 1 calc R . . . .
C6 C 0.9154(2) 1.1444(9) 0.3608(3) 0.0374(8) Uani 1 1 d . . . . .
H6 H 0.9673 1.2668 0.3946 0.045 Uiso 1 1 calc R . . . .
C7 C 0.8541(2) 1.0250(9) 0.4157(3) 0.0361(8) Uani 1 1 d . . . . .
C1 C 0.6333(2) 0.7569(8) 0.3968(3) 0.0367(8) Uani 1 1 d . . . . .
H1 H 0.6129 0.8787 0.3343 0.044 Uiso 1 1 calc R . . . .
C8 C 0.5662(2) 0.6186(8) 0.4504(2) 0.0350(8) Uani 1 1 d . . . . .
C9 C 0.5907(2) 0.4259(8) 0.5399(3) 0.0328(8) Uani 1 1 d . . . . .
H9 H 0.6522 0.3731 0.5669 0.039 Uiso 1 1 calc R . . . .
C10 C 0.5250(2) 0.3101(9) 0.5900(3) 0.0364(8) Uani 1 1 d . . . . .
H10 H 0.5420 0.1820 0.6519 0.044 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C3 1.360(4) . ?
F2 C7 1.354(4) . ?
N1 C2 1.418(4) . ?
N1 C1 1.278(4) . ?
C2 C3 1.390(5) . ?
C2 C7 1.393(5) . ?
C3 C4 1.382(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.382(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.372(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.385(4) . ?
C1 H1 0.9500 . ?
C1 C8 1.469(4) . ?
C8 C9 1.389(5) . ?
C8 C10 1.404(5) 3_666 ?
C9 H9 0.9500 . ?
C9 C10 1.393(4) . ?
C10 C8 1.404(5) 3_666 ?
C10 H10 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 C2 117.7(3) . . ?
C3 C2 N1 124.5(3) . . ?
C3 C2 C7 114.9(3) . . ?
C7 C2 N1 120.4(3) . . ?
F1 C3 C2 117.6(3) . . ?
F1 C3 C4 118.2(3) . . ?
C4 C3 C2 124.2(3) . . ?
C3 C4 H4 121.1 . . ?
C5 C4 C3 117.8(3) . . ?
C5 C4 H4 121.1 . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 H6 120.5 . . ?
C5 C6 C7 119.1(3) . . ?
C7 C6 H6 120.5 . . ?
F2 C7 C2 117.8(3) . . ?
F2 C7 C6 119.3(3) . . ?
C6 C7 C2 122.9(3) . . ?
N1 C1 H1 118.6 . . ?
N1 C1 C8 122.7(3) . . ?
C8 C1 H1 118.6 . . ?
C9 C8 C1 122.0(3) . . ?
C9 C8 C10 119.7(3) . 3_666 ?
C10 C8 C1 118.4(3) 3_666 . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 119.9(3) . . ?
C10 C9 H9 120.0 . . ?
C8 C10 H10 119.8 3_666 . ?
C9 C10 C8 120.4(3) . 3_666 ?
C9 C10 H10 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C3 C4 C5 -176.9(3) . . . . ?
N1 C2 C3 F1 1.2(5) . . . . ?
N1 C2 C3 C4 -177.0(3) . . . . ?
N1 C2 C7 F2 -4.0(5) . . . . ?
N1 C2 C7 C6 177.1(3) . . . . ?
N1 C1 C8 C9 -2.7(5) . . . . ?
N1 C1 C8 C10 176.3(3) . . . 3_666 ?
C2 N1 C1 C8 176.9(3) . . . . ?
C2 C3 C4 C5 1.3(5) . . . . ?
C3 C2 C7 F2 -178.8(3) . . . . ?
C3 C2 C7 C6 2.3(5) . . . . ?
C3 C4 C5 C6 0.0(5) . . . . ?
C4 C5 C6 C7 -0.1(5) . . . . ?
C5 C6 C7 F2 180.0(3) . . . . ?
C5 C6 C7 C2 -1.2(5) . . . . ?
C7 C2 C3 F1 175.8(3) . . . . ?
C7 C2 C3 C4 -2.4(5) . . . . ?
C1 N1 C2 C3 -48.2(5) . . . . ?
C1 N1 C2 C7 137.5(3) . . . . ?
C1 C8 C9 C10 177.8(3) . . . . ?
C8 C9 C10 C8 1.2(5) . . . 3_666 ?
C10 C8 C9 C10 -1.2(5) 3_666 . . . ?

_olex2_exptl_crystal_mounting_method 'cryo loop'
_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_20
_database_code_depnum_ccdc_archive 'CCDC 1562531'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7CE01872J 2017
_audit_update_record             
;
2017-07-17 deposited with the CCDC.
2018-01-10 downloaded from the CCDC.
;
_audit_creation_date             2017-07-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C10 H6 F2 N)'
_chemical_formula_sum            'C20 H12 F4 N2'
_chemical_formula_weight         356.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   32.026(12)
_cell_length_b                   3.8110(11)
_cell_length_c                   13.037(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.569(16)
_cell_angle_gamma                90
_cell_volume                     1573.4(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3578
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.1
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing 1995'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12787
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_min         3.130
_diffrn_ambient_temperature      100.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
scan:
	Number of images: 629
	           Slice: -69.0000 - 119.7000
	     Image width: 0.3000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 120.0000
	             XTD: 49.8600
	          2theta: 29.8900
scan:
	Number of images: 553
	           Slice: -69.0000 - 96.9000
	     Image width: 0.3000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 240.0000
	             XTD: 49.8600
	          2theta: 29.8900
scan:
	Number of images: 483
	           Slice: -69.0000 - 75.9000
	     Image width: 0.3000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 0.0000
	             XTD: 49.8600
	          2theta: 29.8900
;
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Cryo loop'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.001156
_diffrn_orient_matrix_UB_12      0.015909
_diffrn_orient_matrix_UB_13      -0.075914
_diffrn_orient_matrix_UB_21      -0.252347
_diffrn_orient_matrix_UB_22      0.069532
_diffrn_orient_matrix_UB_23      0.018414
_diffrn_orient_matrix_UB_31      0.008477
_diffrn_orient_matrix_UB_32      0.030384
_diffrn_orient_matrix_UB_33      0.001431
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           12.0
_diffrn_source_power             0.6
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2677
_reflns_number_total             3576
_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       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_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         0.329
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3576
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0554
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0778P)²+0.5672P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1398
_refine_ls_wR_factor_ref         0.1608
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C3A(H3A), C5A(H5A), C7A(H7A), C9A(H9A), C10A(H10A), C1B(H1B),
 C7B(H7B), C5B(H5B), C3B(H3B), C9B(H9B), C10B(H10B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1A F 0.75515(4) 0.5186(4) 0.11450(10) 0.0394(4) Uani 1 1 d . . . . .
F2A F 0.86086(4) 0.1659(4) 0.38341(9) 0.0346(3) Uani 1 1 d . . . . .
N1A N 0.94011(5) 0.7456(4) 0.11959(12) 0.0235(4) Uani 1 1 d . . . . .
C1A C 0.90107(6) 0.7430(5) 0.08164(14) 0.0233(4) Uani 1 1 d . . . . .
H1A H 0.8925 0.8374 0.0144 0.028 Uiso 1 1 calc R . . . .
C2A C 0.86896(6) 0.5972(5) 0.13953(14) 0.0219(4) Uani 1 1 d . . . . .
C3A C 0.82638(6) 0.6220(5) 0.09778(15) 0.0251(4) Uani 1 1 d . . . . .
H3A H 0.8180 0.7253 0.0316 0.030 Uiso 1 1 calc R . . . .
C4A C 0.79683(6) 0.4934(6) 0.15456(16) 0.0269(4) Uani 1 1 d . . . . .
C5A C 0.80714(6) 0.3404(6) 0.25079(15) 0.0269(4) Uani 1 1 d . . . . .
H5A H 0.7862 0.2549 0.2889 0.032 Uiso 1 1 calc R . . . .
C6A C 0.84957(6) 0.3186(5) 0.28859(14) 0.0250(4) Uani 1 1 d . . . . .
C7A C 0.88099(6) 0.4401(5) 0.23674(15) 0.0246(4) Uani 1 1 d . . . . .
H7A H 0.9099 0.4185 0.2657 0.030 Uiso 1 1 calc R . . . .
C8A C 0.96944(6) 0.8753(5) 0.05709(14) 0.0232(4) Uani 1 1 d . . . . .
C9A C 1.00509(6) 1.0506(5) 0.10682(15) 0.0240(4) Uani 1 1 d . . . . .
H9A H 1.0088 1.0823 0.1799 0.029 Uiso 1 1 calc R . . . .
C10A C 1.03503(6) 1.1784(5) 0.05043(14) 0.0241(4) Uani 1 1 d . . . . .
H10A H 1.0588 1.3032 0.0846 0.029 Uiso 1 1 calc R . . . .
F1B F 0.74024(4) 0.8041(4) 0.35196(10) 0.0391(4) Uani 1 1 d . . . . .
F2B F 0.64493(4) 0.2411(4) 0.53691(9) 0.0358(3) Uani 1 1 d . . . . .
N1B N 0.56188(5) 0.4653(5) 0.17842(13) 0.0287(4) Uani 1 1 d . . . . .
C1B C 0.59642(6) 0.6368(6) 0.18524(15) 0.0275(4) Uani 1 1 d . . . . .
H1B H 0.6008 0.7924 0.1310 0.033 Uiso 1 1 calc R . . . .
C2B C 0.62944(6) 0.5974(6) 0.27566(15) 0.0274(4) Uani 1 1 d . . . . .
C7B C 0.62070(6) 0.4317(6) 0.36620(15) 0.0275(4) Uani 1 1 d . . . . .
H7B H 0.5933 0.3444 0.3710 0.033 Uiso 1 1 calc R . . . .
C6B C 0.65297(7) 0.3995(6) 0.44769(16) 0.0289(5) Uani 1 1 d . . . . .
C5B C 0.69353(7) 0.5189(6) 0.44670(16) 0.0296(5) Uani 1 1 d . . . . .
H5B H 0.7152 0.4916 0.5044 0.036 Uiso 1 1 calc R . . . .
C4B C 0.70055(6) 0.6811(6) 0.35606(17) 0.0300(5) Uani 1 1 d . . . . .
C3B C 0.66991(7) 0.7242(6) 0.27118(16) 0.0297(5) Uani 1 1 d . . . . .
H3B H 0.6762 0.8383 0.2106 0.036 Uiso 1 1 calc R . . . .
C8B C 0.53170(6) 0.4897(5) 0.08742(16) 0.0267(4) Uani 1 1 d . . . . .
C9B C 0.49036(6) 0.3948(6) 0.09557(16) 0.0294(5) Uani 1 1 d . . . . .
H9B H 0.4836 0.3206 0.1607 0.035 Uiso 1 1 calc R . . . .
C10B C 0.45896(7) 0.4068(6) 0.01016(16) 0.0289(5) Uani 1 1 d . . . . .
H10B H 0.4308 0.3445 0.0176 0.035 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
F1A C4A 1.362(2) . ?
F2A C6A 1.365(2) . ?
N1A C1A 1.274(2) . ?
N1A C8A 1.421(2) . ?
C1A H1A 0.9500 . ?
C1A C2A 1.472(3) . ?
C2A C3A 1.394(3) . ?
C2A C7A 1.403(3) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.376(3) . ?
C4A C5A 1.378(3) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.377(3) . ?
C6A C7A 1.374(3) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.396(3) . ?
C8A C10A 1.403(3) 3_775 ?
C9A H9A 0.9500 . ?
C9A C10A 1.381(3) . ?
C10A C8A 1.403(3) 3_775 ?
C10A H10A 0.9500 . ?
F1B C4B 1.363(2) . ?
F2B C6B 1.369(2) . ?
N1B C1B 1.276(3) . ?
N1B C8B 1.417(3) . ?
C1B H1B 0.9500 . ?
C1B C2B 1.469(3) . ?
C2B C7B 1.403(3) . ?
C2B C3B 1.393(3) . ?
C7B H7B 0.9500 . ?
C7B C6B 1.373(3) . ?
C6B C5B 1.378(3) . ?
C5B H5B 0.9500 . ?
C5B C4B 1.381(3) . ?
C4B C3B 1.375(3) . ?
C3B H3B 0.9500 . ?
C8B C9B 1.392(3) . ?
C8B C10B 1.406(3) 3_665 ?
C9B H9B 0.9500 . ?
C9B C10B 1.386(3) . ?
C10B C8B 1.406(3) 3_665 ?
C10B H10B 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
C1A N1A C8A 118.32(16) . . ?
N1A C1A H1A 119.2 . . ?
N1A C1A C2A 121.59(18) . . ?
C2A C1A H1A 119.2 . . ?
C3A C2A C1A 119.45(17) . . ?
C3A C2A C7A 120.17(17) . . ?
C7A C2A C1A 120.37(17) . . ?
C2A C3A H3A 120.7 . . ?
C4A C3A C2A 118.51(18) . . ?
C4A C3A H3A 120.7 . . ?
F1A C4A C3A 118.82(18) . . ?
F1A C4A C5A 117.83(17) . . ?
C3A C4A C5A 123.35(18) . . ?
C4A C5A H5A 121.9 . . ?
C6A C5A C4A 116.17(18) . . ?
C6A C5A H5A 121.9 . . ?
F2A C6A C5A 117.63(17) . . ?
F2A C6A C7A 118.33(17) . . ?
C7A C6A C5A 124.04(18) . . ?
C2A C7A H7A 121.1 . . ?
C6A C7A C2A 117.77(18) . . ?
C6A C7A H7A 121.1 . . ?
C9A C8A N1A 117.70(17) . . ?
C9A C8A C10A 119.23(18) . 3_775 ?
C10A C8A N1A 123.01(17) 3_775 . ?
C8A C9A H9A 119.8 . . ?
C10A C9A C8A 120.40(18) . . ?
C10A C9A H9A 119.8 . . ?
C8A C10A H10A 119.8 3_775 . ?
C9A C10A C8A 120.34(18) . 3_775 ?
C9A C10A H10A 119.8 . . ?
C1B N1B C8B 120.03(18) . . ?
N1B C1B H1B 119.5 . . ?
N1B C1B C2B 121.08(19) . . ?
C2B C1B H1B 119.5 . . ?
C7B C2B C1B 120.73(18) . . ?
C3B C2B C1B 119.61(19) . . ?
C3B C2B C7B 119.66(19) . . ?
C2B C7B H7B 121.0 . . ?
C6B C7B C2B 118.01(19) . . ?
C6B C7B H7B 121.0 . . ?
F2B C6B C7B 118.80(18) . . ?
F2B C6B C5B 116.78(18) . . ?
C7B C6B C5B 124.42(19) . . ?
C6B C5B H5B 122.3 . . ?
C6B C5B C4B 115.44(19) . . ?
C4B C5B H5B 122.3 . . ?
F1B C4B C5B 117.31(19) . . ?
F1B C4B C3B 119.03(19) . . ?
C3B C4B C5B 123.66(19) . . ?
C2B C3B H3B 120.6 . . ?
C4B C3B C2B 118.81(19) . . ?
C4B C3B H3B 120.6 . . ?
C9B C8B N1B 117.18(18) . . ?
C9B C8B C10B 118.36(19) . 3_665 ?
C10B C8B N1B 124.43(18) 3_665 . ?
C8B C9B H9B 119.5 . . ?
C10B C9B C8B 121.00(19) . . ?
C10B C9B H9B 119.5 . . ?
C8B C10B H10B 119.7 3_665 . ?
C9B C10B C8B 120.63(19) . 3_665 ?
C9B C10B H10B 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1A C4A C5A C6A 179.80(18) . . . . ?
F2A C6A C7A C2A -179.85(17) . . . . ?
N1A C1A C2A C3A 175.62(18) . . . . ?
N1A C1A C2A C7A -3.3(3) . . . . ?
N1A C8A C9A C10A 179.10(18) . . . . ?
C1A N1A C8A C9A 146.58(19) . . . . ?
C1A N1A C8A C10A -36.2(3) . . . 3_775 ?
C1A C2A C3A C4A -178.09(18) . . . . ?
C1A C2A C7A C6A 178.00(18) . . . . ?
C2A C3A C4A F1A 179.62(17) . . . . ?
C2A C3A C4A C5A -0.1(3) . . . . ?
C3A C2A C7A C6A -0.9(3) . . . . ?
C3A C4A C5A C6A -0.5(3) . . . . ?
C4A C5A C6A F2A -179.50(18) . . . . ?
C4A C5A C6A C7A 0.4(3) . . . . ?
C5A C6A C7A C2A 0.3(3) . . . . ?
C7A C2A C3A C4A 0.8(3) . . . . ?
C8A N1A C1A C2A 177.01(17) . . . . ?
C8A C9A C10A C8A -1.8(3) . . . 3_775 ?
C10A C8A C9A C10A 1.8(3) 3_775 . . . ?
F1B C4B C3B C2B 179.85(18) . . . . ?
F2B C6B C5B C4B -179.29(18) . . . . ?
N1B C1B C2B C7B -13.8(3) . . . . ?
N1B C1B C2B C3B 165.8(2) . . . . ?
N1B C8B C9B C10B -179.24(19) . . . . ?
C1B N1B C8B C9B -160.0(2) . . . . ?
C1B N1B C8B C10B 21.9(3) . . . 3_665 ?
C1B C2B C7B C6B 179.32(19) . . . . ?
C1B C2B C3B C4B -179.20(18) . . . . ?
C2B C7B C6B F2B 179.49(18) . . . . ?
C2B C7B C6B C5B 0.0(3) . . . . ?
C7B C2B C3B C4B 0.4(3) . . . . ?
C7B C6B C5B C4B 0.3(3) . . . . ?
C6B C5B C4B F1B 179.81(18) . . . . ?
C6B C5B C4B C3B -0.1(3) . . . . ?
C5B C4B C3B C2B -0.2(3) . . . . ?
C3B C2B C7B C6B -0.3(3) . . . . ?
C8B N1B C1B C2B -175.77(18) . . . . ?
C8B C9B C10B C8B 1.0(4) . . . 3_665 ?
C10B C8B C9B C10B -1.0(3) 3_665 . . . ?

_olex2_exptl_crystal_mounting_method 'cryo loop'
_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_7
_database_code_depnum_ccdc_archive 'CCDC 1562536'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7CE01872J 2017
_audit_update_record             
;
2017-07-17 deposited with the CCDC.
2018-01-10 downloaded from the CCDC.
;
_audit_creation_date             2017-07-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C10 H6 F2 N)'
_chemical_formula_sum            'C20 H12 F4 N2'
_chemical_formula_weight         356.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   35.40(2)
_cell_length_b                   3.766(2)
_cell_length_c                   11.682(8)
_cell_angle_alpha                90
_cell_angle_beta                 99.19(3)
_cell_angle_gamma                90
_cell_volume                     1537.0(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1544
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.8
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.818
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessings, 1995'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0829
_diffrn_reflns_av_unetI/netI     0.0823
_diffrn_reflns_Laue_measured_fraction_full 0.755
_diffrn_reflns_Laue_measured_fraction_max 0.788
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6612
_diffrn_reflns_point_group_measured_fraction_full 0.755
_diffrn_reflns_point_group_measured_fraction_max 0.788
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.490
_diffrn_reflns_theta_min         1.748
_diffrn_ambient_temperature      100.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.755
_diffrn_measured_fraction_theta_max 0.788
_diffrn_measurement_details      
;
scan:
	Number of images: 600
	           Slice: -70.0000 - 110.0000
	     Image width: 0.3000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 45.0000
	             XTD: 49.8600
	          2theta: 29.8900
scan:
	Number of images: 600
	           Slice: -70.0000 - 110.0000
	     Image width: 0.3000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 135.0000
	             XTD: 49.8600
	          2theta: 29.8900
scan:
	Number of images: 600
	           Slice: -70.0000 - 110.0000
	     Image width: 0.3000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 225.0000
	             XTD: 49.8600
	          2theta: 29.8900
;
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Cryo loop'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.063562
_diffrn_orient_matrix_UB_12      -0.058699
_diffrn_orient_matrix_UB_13      -0.000336
_diffrn_orient_matrix_UB_21      -0.002828
_diffrn_orient_matrix_UB_22      0.004589
_diffrn_orient_matrix_UB_23      -0.266463
_diffrn_orient_matrix_UB_31      0.015809
_diffrn_orient_matrix_UB_32      -0.023752
_diffrn_orient_matrix_UB_33      -0.000577
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           12.0
_diffrn_source_power             0.6
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1492
_reflns_number_total             2438
_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       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_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         0.560
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.124
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.362
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2438
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1659
_refine_ls_R_factor_gt           0.1308
_refine_ls_restrained_S_all      1.362
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3671
_refine_ls_wR_factor_ref         0.4232
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.756(8)
 0.244(8)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C4B(H4B), C10A(H10A), C9B(H9B), C7A(H7A), C9A(H9A), C1B(H1B), C7B(H7B),
 C5B(H5B), C5A(H5A), C1A(H1A), C10B(H10B), C4A(H4A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1B F 0.38864(11) 0.1328(14) 0.2959(5) 0.0355(12) Uani 1 1 d . . . . .
F1A F 0.11006(12) -0.6236(13) 0.4038(4) 0.0369(12) Uani 1 1 d . . . . .
F2A F 0.21808(12) -0.3920(15) 0.1328(5) 0.0422(13) Uani 1 1 d . . . . .
F2B F 0.28170(12) -0.1968(19) -0.0724(5) 0.0486(14) Uani 1 1 d . . . . .
N1A N 0.08793(14) -0.2697(18) 0.1983(6) 0.0291(15) Uani 1 1 d . . . . .
N1B N 0.41178(15) -0.2377(17) 0.1151(5) 0.0241(13) Uani 1 1 d . . . . .
C4B C 0.3246(2) 0.137(2) 0.2074(8) 0.0350(18) Uani 1 1 d . . . . .
H4B H 0.3178 0.2502 0.2739 0.042 Uiso 1 1 calc R . . . .
C10A C -0.01203(17) -0.0230(19) -0.1178(7) 0.0253(14) Uani 1 1 d . . . . .
H10A H -0.0206 -0.0378 -0.1990 0.030 Uiso 1 1 calc R . . . .
C9B C 0.48737(17) -0.5175(19) 0.1088(7) 0.0258(14) Uani 1 1 d . . . . .
H9B H 0.4788 -0.5429 0.1815 0.031 Uiso 1 1 calc R . . . .
C7A C 0.15435(18) -0.342(2) 0.1618(7) 0.0294(17) Uani 1 1 d . . . . .
H7A H 0.1483 -0.2288 0.0884 0.035 Uiso 1 1 calc R . . . .
C3A C 0.13728(17) -0.5674(19) 0.3356(7) 0.0261(15) Uani 1 1 d . . . . .
C2A C 0.12606(18) -0.3967(19) 0.2299(7) 0.0254(14) Uani 1 1 d . . . . .
C9A C 0.02366(19) -0.150(2) -0.0728(7) 0.0289(16) Uani 1 1 d . . . . .
H9A H 0.0396 -0.2513 -0.1223 0.035 Uiso 1 1 calc R . . . .
C1B C 0.42656(16) -0.2293(19) 0.0233(6) 0.0246(14) Uani 1 1 d . . . . .
H1B H 0.4120 -0.1254 -0.0436 0.029 Uiso 1 1 calc R . . . .
C8A C 0.03616(17) -0.1293(18) 0.0459(6) 0.0245(15) Uani 1 1 d . . . . .
C7B C 0.34518(19) -0.197(3) 0.0152(7) 0.0370(19) Uani 1 1 d . . . . .
H7B H 0.3521 -0.3028 -0.0525 0.044 Uiso 1 1 calc R . . . .
C5B C 0.29630(19) 0.0553(19) 0.1119(9) 0.0343(19) Uani 1 1 d . . . . .
H5B H 0.2703 0.1194 0.1106 0.041 Uiso 1 1 calc R . . . .
C6B C 0.3083(2) -0.126(2) 0.0188(8) 0.0338(17) Uani 1 1 d . . . . .
C5A C 0.20189(18) -0.616(2) 0.3072(7) 0.0332(17) Uani 1 1 d . . . . .
H5A H 0.2277 -0.6827 0.3329 0.040 Uiso 1 1 calc R . . . .
C3B C 0.36207(19) 0.054(2) 0.2040(7) 0.0308(16) Uani 1 1 d . . . . .
C8B C 0.46358(18) -0.3646(18) 0.0130(6) 0.0257(15) Uani 1 1 d . . . . .
C6A C 0.19123(16) -0.4517(19) 0.2016(7) 0.0273(15) Uani 1 1 d . . . . .
C1A C 0.07414(16) -0.281(2) 0.0926(7) 0.0280(16) Uani 1 1 d . . . . .
H1A H 0.0886 -0.3914 0.0405 0.034 Uiso 1 1 calc R . . . .
C10B C 0.47592(18) -0.369(2) -0.0935(7) 0.0303(16) Uani 1 1 d . . . . .
H10B H 0.4587 -0.2912 -0.1596 0.036 Uiso 1 1 calc R . . . .
C4A C 0.17393(18) -0.679(2) 0.3746(7) 0.0323(17) Uani 1 1 d . . . . .
H4A H 0.1800 -0.7987 0.4468 0.039 Uiso 1 1 calc R . . . .
C2B C 0.37405(17) -0.1188(19) 0.1105(7) 0.0280(16) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1B C3B 1.343(8) . ?
F1A C3A 1.361(8) . ?
F2A C6A 1.358(8) . ?
F2B C6B 1.332(9) . ?
N1A C2A 1.424(8) . ?
N1A C1A 1.255(10) . ?
N1B C1B 1.266(9) . ?
N1B C2B 1.402(8) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.410(12) . ?
C4B C3B 1.369(10) . ?
C10A H10A 0.9500 . ?
C10A C9A 1.375(9) . ?
C10A C8A 1.412(9) 3 ?
C9B H9B 0.9500 . ?
C9B C8B 1.412(10) . ?
C9B C10B 1.406(9) 3_645 ?
C7A H7A 0.9500 . ?
C7A C2A 1.390(10) . ?
C7A C6A 1.378(9) . ?
C3A C2A 1.392(10) . ?
C3A C4A 1.371(9) . ?
C9A H9A 0.9500 . ?
C9A C8A 1.389(10) . ?
C1B H1B 0.9500 . ?
C1B C8B 1.429(9) . ?
C8A C10A 1.411(9) 3 ?
C8A C1A 1.482(9) . ?
C7B H7B 0.9500 . ?
C7B C6B 1.340(10) . ?
C7B C2B 1.417(10) . ?
C5B H5B 0.9500 . ?
C5B C6B 1.405(13) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.377(11) . ?
C5A C4A 1.381(11) . ?
C3B C2B 1.394(11) . ?
C8B C10B 1.383(10) . ?
C1A H1A 0.9500 . ?
C10B C9B 1.406(9) 3_645 ?
C10B H10B 0.9500 . ?
C4A H4A 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
C1A N1A C2A 116.5(6) . . ?
C1B N1B C2B 118.6(6) . . ?
C5B C4B H4B 120.1 . . ?
C3B C4B H4B 120.1 . . ?
C3B C4B C5B 119.7(8) . . ?
C9A C10A H10A 119.3 . . ?
C9A C10A C8A 121.3(7) . 3 ?
C8A C10A H10A 119.3 3 . ?
C8B C9B H9B 121.0 . . ?
C10B C9B H9B 121.0 3_645 . ?
C10B C9B C8B 118.0(7) 3_645 . ?
C2A C7A H7A 120.3 . . ?
C6A C7A H7A 120.3 . . ?
C6A C7A C2A 119.5(7) . . ?
F1A C3A C2A 117.6(6) . . ?
F1A C3A C4A 118.5(7) . . ?
C4A C3A C2A 123.9(7) . . ?
C7A C2A N1A 122.8(7) . . ?
C7A C2A C3A 116.5(6) . . ?
C3A C2A N1A 120.6(7) . . ?
C10A C9A H9A 120.3 . . ?
C10A C9A C8A 119.3(7) . . ?
C8A C9A H9A 120.3 . . ?
N1B C1B H1B 117.6 . . ?
N1B C1B C8B 124.8(6) . . ?
C8B C1B H1B 117.6 . . ?
C10A C8A C1A 122.5(7) 3 . ?
C9A C8A C10A 119.4(6) . 3 ?
C9A C8A C1A 118.1(7) . . ?
C6B C7B H7B 119.5 . . ?
C6B C7B C2B 121.1(8) . . ?
C2B C7B H7B 119.5 . . ?
C4B C5B H5B 121.5 . . ?
C6B C5B C4B 117.0(6) . . ?
C6B C5B H5B 121.5 . . ?
F2B C6B C7B 120.1(8) . . ?
F2B C6B C5B 117.0(7) . . ?
C7B C6B C5B 122.6(8) . . ?
C6A C5A H5A 121.0 . . ?
C6A C5A C4A 118.0(6) . . ?
C4A C5A H5A 121.0 . . ?
F1B C3B C4B 118.9(7) . . ?
F1B C3B C2B 117.9(6) . . ?
C4B C3B C2B 123.2(7) . . ?
C9B C8B C1B 121.2(6) . . ?
C10B C8B C9B 118.3(6) . . ?
C10B C8B C1B 120.4(7) . . ?
F2A C6A C7A 117.7(7) . . ?
F2A C6A C5A 119.1(6) . . ?
C5A C6A C7A 123.2(7) . . ?
N1A C1A C8A 122.4(7) . . ?
N1A C1A H1A 118.8 . . ?
C8A C1A H1A 118.8 . . ?
C9B C10B H10B 118.3 3_645 . ?
C8B C10B C9B 123.3(7) . 3_645 ?
C8B C10B H10B 118.3 . . ?
C3A C4A C5A 118.9(7) . . ?
C3A C4A H4A 120.6 . . ?
C5A C4A H4A 120.6 . . ?
N1B C2B C7B 121.8(7) . . ?
C3B C2B N1B 121.7(7) . . ?
C3B C2B C7B 116.2(6) . . ?

_olex2_exptl_crystal_mounting_method 'cryo loop'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.756(8)
2 0.244(8)

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1562534'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7CE01872J 2017
_audit_update_record             
;
2017-07-17 deposited with the CCDC.
2018-01-10 downloaded from the CCDC.
;
_audit_creation_date             2017-07-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H12 F4 N2'
_chemical_formula_sum            'C20 H12 F4 N2'
_chemical_formula_weight         356.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   16.870(4)
_cell_length_b                   3.7774(7)
_cell_length_c                   12.010(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.317(11)
_cell_angle_gamma                90
_cell_volume                     762.1(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1567
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.4
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessings, 1995'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7231
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_min         2.425
_diffrn_ambient_temperature      100.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
scan:
	Number of images: 629
	           Slice: -69.0000 - 119.7000
	     Image width: 0.3000
	        Exp time: 22.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 0.0000
	             XTD: 49.8600
	          2theta: 29.8900
scan:
	Number of images: 629
	           Slice: -69.0000 - 119.7000
	     Image width: 0.3000
	        Exp time: 22.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 120.0000
	             XTD: 49.8600
	          2theta: 29.8900
scan:
	Number of images: 544
	           Slice: -69.0000 - 94.2000
	     Image width: 0.3000
	        Exp time: 22.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 240.0000
	             XTD: 49.8600
	          2theta: 29.8900
;
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Cryo loop'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.024192
_diffrn_orient_matrix_UB_12      0.079783
_diffrn_orient_matrix_UB_13      0.006477
_diffrn_orient_matrix_UB_21      0.249350
_diffrn_orient_matrix_UB_22      -0.071294
_diffrn_orient_matrix_UB_23      -0.053152
_diffrn_orient_matrix_UB_31      -0.008523
_diffrn_orient_matrix_UB_32      0.013031
_diffrn_orient_matrix_UB_33      -0.057461
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           12.0
_diffrn_source_power             0.6
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1374
_reflns_number_total             1735
_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       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_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         0.625
_refine_diff_density_min         -0.593
_refine_diff_density_rms         0.155
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1735
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0505
_refine_ls_restrained_S_all      1.093
_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)+(0.1462P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1457
_refine_ls_wR_factor_ref         0.2039
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9), C5(H5), C1(H1), C6(H6), C7(H7)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.72906(6) 0.3882(3) 0.18152(9) 0.0255(4) Uani 1 1 d . . . . .
F2 F 0.88149(7) 0.2410(3) 0.15837(10) 0.0278(4) Uani 1 1 d . . . . .
N1 N 0.68191(9) 0.7576(4) 0.36345(14) 0.0193(4) Uani 1 1 d . . . . .
C2 C 0.76237(11) 0.6566(5) 0.35831(16) 0.0180(4) Uani 1 1 d . . . . .
C8 C 0.57459(11) 0.8710(5) 0.47810(15) 0.0181(5) Uani 1 1 d . . . . .
C10 C 0.47560(11) 0.9766(5) 0.60768(16) 0.0192(5) Uani 1 1 d . . . . .
H10 H 0.4590 0.9594 0.6809 0.023 Uiso 1 1 calc R . . . .
C9 C 0.54990(11) 0.8500(5) 0.58584(16) 0.0196(5) Uani 1 1 d . . . . .
H9 H 0.5842 0.7485 0.6445 0.024 Uiso 1 1 calc R . . . .
C3 C 0.78447(11) 0.4862(5) 0.26359(16) 0.0195(5) Uani 1 1 d . . . . .
C4 C 0.86360(12) 0.4092(5) 0.25161(16) 0.0207(5) Uani 1 1 d . . . . .
C5 C 0.92298(11) 0.5009(5) 0.33263(16) 0.0216(5) Uani 1 1 d . . . . .
H5 H 0.9771 0.4476 0.3238 0.026 Uiso 1 1 calc R . . . .
C1 C 0.65361(11) 0.7366(5) 0.45861(16) 0.0184(5) Uani 1 1 d . . . . .
H1 H 0.6852 0.6295 0.5191 0.022 Uiso 1 1 calc R . . . .
C6 C 0.90194(11) 0.6732(6) 0.42757(18) 0.0223(5) Uani 1 1 d . . . . .
H6 H 0.9422 0.7393 0.4843 0.027 Uiso 1 1 calc R . . . .
C7 C 0.82280(12) 0.7504(5) 0.44087(17) 0.0199(5) Uani 1 1 d . . . . .
H7 H 0.8096 0.8679 0.5066 0.024 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C3 1.346(2) . ?
F2 C4 1.346(2) . ?
N1 C2 1.417(2) . ?
N1 C1 1.281(3) . ?
C2 C3 1.388(3) . ?
C2 C7 1.400(3) . ?
C8 C10 1.396(3) 3_676 ?
C8 C9 1.398(3) . ?
C8 C1 1.465(3) . ?
C10 C8 1.396(3) 3_676 ?
C10 H10 0.9500 . ?
C10 C9 1.389(3) . ?
C9 H9 0.9500 . ?
C3 C4 1.387(3) . ?
C4 C5 1.375(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(3) . ?
C1 H1 0.9500 . ?
C6 H6 0.9500 . ?
C6 C7 1.390(3) . ?
C7 H7 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 C2 117.38(16) . . ?
C3 C2 N1 119.45(17) . . ?
C3 C2 C7 117.69(17) . . ?
C7 C2 N1 122.59(17) . . ?
C10 C8 C9 119.63(17) 3_676 . ?
C10 C8 C1 121.57(17) 3_676 . ?
C9 C8 C1 118.79(17) . . ?
C8 C10 H10 120.0 3_676 . ?
C9 C10 C8 119.93(18) . 3_676 ?
C9 C10 H10 120.0 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.44(18) . . ?
C10 C9 H9 119.8 . . ?
F1 C3 C2 120.46(16) . . ?
F1 C3 C4 118.43(17) . . ?
C4 C3 C2 121.11(18) . . ?
F2 C4 C3 118.54(17) . . ?
F2 C4 C5 120.20(17) . . ?
C5 C4 C3 121.26(18) . . ?
C4 C5 H5 120.8 . . ?
C4 C5 C6 118.35(17) . . ?
C6 C5 H5 120.8 . . ?
N1 C1 C8 122.74(17) . . ?
N1 C1 H1 118.6 . . ?
C8 C1 H1 118.6 . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C7 120.96(18) . . ?
C7 C6 H6 119.5 . . ?
C2 C7 H7 119.7 . . ?
C6 C7 C2 120.63(18) . . ?
C6 C7 H7 119.7 . . ?

_olex2_exptl_crystal_mounting_method 'cryo loop'
_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_13
_database_code_depnum_ccdc_archive 'CCDC 1562524'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7CE01872J 2017
_audit_update_record             
;
2017-07-17 deposited with the CCDC.
2018-01-10 downloaded from the CCDC.
;
_audit_creation_date             2017-06-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 F2 N2'
_chemical_formula_sum            'C20 H14 F2 N2'
_chemical_formula_weight         320.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H14 N2 F2'
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'

_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                   17.2860(18)
_cell_length_b                   6.1726(8)
_cell_length_c                   7.0329(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.883(10)
_cell_angle_gamma                90
_cell_volume                     749.46(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3184
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      32.8870
_cell_measurement_theta_min      2.2940
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.16470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing 1995'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6536
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         32.882
_diffrn_reflns_theta_min         2.359
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00 119.70   0.30    8.00    --   29.89  54.00 240.00  629
  2  ω    -69.00 119.70   0.30    8.00    --   29.89  54.00   0.00  629
;
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0400981000
_diffrn_orient_matrix_UB_12      0.0160104000
_diffrn_orient_matrix_UB_13      -0.0125552000
_diffrn_orient_matrix_UB_21      -0.0072798000
_diffrn_orient_matrix_UB_22      0.0004911000
_diffrn_orient_matrix_UB_23      -0.1000143000
_diffrn_orient_matrix_UB_31      -0.0054957000
_diffrn_orient_matrix_UB_32      0.1138603000
_diffrn_orient_matrix_UB_33      0.0018382000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1878
_reflns_number_total             2580
_reflns_odcompleteness_completeness 91.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.81
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.814
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.107
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         2580
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1004
_refine_ls_R_factor_gt           0.0852
_refine_ls_restrained_S_all      1.116
_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)+(0.1755P)²+0.0061P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2345
_refine_ls_wR_factor_ref         0.2755
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9), C7(H7), C1(H1), C6(H6), C5(H5), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.94579(5) 0.18195(17) 0.42502(16) 0.0390(4) Uani 1 1 d . . . . .
N1 N 0.65353(7) 0.1349(2) 0.44647(17) 0.0232(3) Uani 1 1 d . . . . .
C10 C 0.43664(8) 0.1236(2) 0.4377(2) 0.0219(3) Uani 1 1 d . . . . .
H10 H 0.3933 0.2092 0.3962 0.026 Uiso 1 1 calc R . . . .
C9 C 0.51081(8) 0.1967(2) 0.40669(19) 0.0228(4) Uani 1 1 d . . . . .
H9 H 0.5179 0.3297 0.3419 0.027 Uiso 1 1 calc R . . . .
C8 C 0.57551(8) 0.0743(2) 0.47101(19) 0.0221(4) Uani 1 1 d . . . . .
C7 C 0.76678(9) 0.6177(2) 0.3563(2) 0.0261(4) Uani 1 1 d . . . . .
H7 H 0.7256 0.7194 0.3433 0.031 Uiso 1 1 calc R . . . .
C2 C 0.75196(8) 0.4056(2) 0.4116(2) 0.0237(4) Uani 1 1 d . . . . .
C1 C 0.67189(8) 0.3351(2) 0.4399(2) 0.0235(4) Uani 1 1 d . . . . .
H1 H 0.6329 0.4415 0.4536 0.028 Uiso 1 1 calc R . . . .
C6 C 0.84228(9) 0.6805(3) 0.3200(2) 0.0298(4) Uani 1 1 d . . . . .
H6 H 0.8521 0.8243 0.2795 0.036 Uiso 1 1 calc R . . . .
C5 C 0.90316(8) 0.5335(3) 0.3430(2) 0.0307(4) Uani 1 1 d . . . . .
H5 H 0.9547 0.5748 0.3185 0.037 Uiso 1 1 calc R . . . .
C3 C 0.81282(8) 0.2555(3) 0.4364(2) 0.0254(4) Uani 1 1 d . . . . .
H3 H 0.8035 0.1109 0.4752 0.031 Uiso 1 1 calc R . . . .
C4 C 0.88660(8) 0.3261(3) 0.4024(2) 0.0286(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C4 1.3592(17) . ?
N1 C8 1.4183(17) . ?
N1 C1 1.277(2) . ?
C10 H10 0.9500 . ?
C10 C9 1.3866(17) . ?
C10 C8 1.401(2) 3_656 ?
C9 H9 0.9500 . ?
C9 C8 1.406(2) . ?
C8 C10 1.401(2) 3_656 ?
C7 H7 0.9500 . ?
C7 C2 1.393(2) . ?
C7 C6 1.3972(19) . ?
C2 C1 1.4739(19) . ?
C2 C3 1.406(2) . ?
C1 H1 0.9500 . ?
C6 H6 0.9500 . ?
C6 C5 1.393(2) . ?
C5 H5 0.9500 . ?
C5 C4 1.381(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.3800(18) . ?

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 C8 119.93(13) . . ?
C9 C10 H10 119.4 . . ?
C9 C10 C8 121.13(13) . 3_656 ?
C8 C10 H10 119.4 3_656 . ?
C10 C9 H9 119.9 . . ?
C10 C9 C8 120.10(13) . . ?
C8 C9 H9 119.9 . . ?
C10 C8 N1 116.81(13) 3_656 . ?
C10 C8 C9 118.76(12) 3_656 . ?
C9 C8 N1 124.42(13) . . ?
C2 C7 H7 120.0 . . ?
C2 C7 C6 119.90(14) . . ?
C6 C7 H7 120.0 . . ?
C7 C2 C1 120.16(14) . . ?
C7 C2 C3 120.45(12) . . ?
C3 C2 C1 119.37(13) . . ?
N1 C1 C2 121.83(13) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C7 C6 H6 119.8 . . ?
C5 C6 C7 120.34(14) . . ?
C5 C6 H6 119.8 . . ?
C6 C5 H5 120.9 . . ?
C4 C5 C6 118.17(12) . . ?
C4 C5 H5 120.9 . . ?
C2 C3 H3 121.2 . . ?
C4 C3 C2 117.58(14) . . ?
C4 C3 H3 121.2 . . ?
F1 C4 C5 118.42(12) . . ?
F1 C4 C3 118.04(14) . . ?
C3 C4 C5 123.53(14) . . ?

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
C10 C9 C8 N1 180.00(11) . . . . ?
C10 C9 C8 C10 1.4(2) . . . 3_656 ?
C8 N1 C1 C2 -179.03(12) . . . . ?
C8 C10 C9 C8 -1.5(2) 3_656 . . . ?
C7 C2 C1 N1 163.36(14) . . . . ?
C7 C2 C3 C4 -0.6(2) . . . . ?
C7 C6 C5 C4 -0.1(2) . . . . ?
C2 C7 C6 C5 -1.5(2) . . . . ?
C2 C3 C4 F1 -179.65(13) . . . . ?
C2 C3 C4 C5 -1.0(2) . . . . ?
C1 N1 C8 C10 -151.31(14) . . . 3_656 ?
C1 N1 C8 C9 30.1(2) . . . . ?
C1 C2 C3 C4 177.88(12) . . . . ?
C6 C7 C2 C1 -176.65(12) . . . . ?
C6 C7 C2 C3 1.8(2) . . . . ?
C6 C5 C4 F1 179.98(13) . . . . ?
C6 C5 C4 C3 1.4(2) . . . . ?
C3 C2 C1 N1 -15.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.213
_oxdiff_exptl_absorpt_empirical_full_min 0.513
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1562533'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7CE01872J 2017
_audit_update_record             
;
2017-07-17 deposited with the CCDC.
2018-01-10 downloaded from the CCDC.
;
_audit_creation_date             2016-12-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 F2 N2'
_chemical_formula_sum            'C20 H14 F2 N2'
_chemical_formula_weight         320.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.4234(7)
_cell_length_b                   5.6728(5)
_cell_length_c                   36.086(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.003(8)
_cell_angle_gamma                90
_cell_volume                     1513.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3322
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      32.4220
_cell_measurement_theta_min      2.8590
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81049
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.7f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_av_unetI/netI     0.0706
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_limit_l_min       -54
_diffrn_reflns_number            18896
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         32.898
_diffrn_reflns_theta_min         2.754
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.9490
_diffrn_measured_fraction_theta_max 0.9491
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00 105.90   0.30   10.00    --   29.89  54.00 120.00  583
  2  ω    -60.00 118.20   0.30   10.00    --   29.89  54.00   0.00  594
  3  ω    -69.00  91.80   0.30   10.00    --   29.89  54.00 240.00  536
;
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0449206000
_diffrn_orient_matrix_UB_12      0.1083092000
_diffrn_orient_matrix_UB_13      0.0042633000
_diffrn_orient_matrix_UB_21      0.0483775000
_diffrn_orient_matrix_UB_22      -0.0530534000
_diffrn_orient_matrix_UB_23      0.0156280000
_diffrn_orient_matrix_UB_31      0.0696090000
_diffrn_orient_matrix_UB_32      -0.0329303000
_diffrn_orient_matrix_UB_33      -0.0112597000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2675
_reflns_number_total             5393
_reflns_odcompleteness_completeness 94.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.82
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_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         1.269
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.116
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         5393
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.1574
_refine_ls_R_factor_gt           0.0891
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1485P)²+0.0394P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2245
_refine_ls_wR_factor_ref         0.2981
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Shared sites
{N1A, N1B}
{N2A, N2B}
3. Restrained distances
 C11B-C8B
 1.47 with sigma of 0.02
 C1B-C18B
 1.47 with sigma of 0.02
 C20B-C19B
 1.39 with sigma of 0.02
 C9B-C10B
 1.39 with sigma of 0.02
 C8B-C20B
 1.39 with sigma of 0.02
 C8B-C9B
 1.39 with sigma of 0.02
 C18B-C19B
 1.39 with sigma of 0.02
 C10B-C18B
 1.39 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(N1A) = Uanis(N1B)
Uanis(N2A) = Uanis(N2B)
Uanis(C1A) = Uanis(C11B)
Uanis(C8A) = Uanis(C8B)
Uanis(C20A) = Uanis(C20B)
Uanis(C19A) = Uanis(C19B)
Uanis(C18A) = Uanis(C18B)
Uanis(C10A) = Uanis(C10B)
Uanis(C9A) = Uanis(C9B)
Uanis(C11A) = Uanis(C1B)
5. Others
 Sof(C19B)=Sof(H19B)=Sof(C1B)=Sof(H1B)=Sof(C20B)=Sof(H20B)=Sof(C11B)=Sof(H11B)=
 Sof(C18B)=Sof(C8B)=Sof(C9B)=Sof(H9B)=Sof(C10B)=Sof(H10B)=Sof(N1B)=Sof(N2B)=1-
 FVAR(1)
 Sof(C10A)=Sof(H10A)=Sof(C8A)=Sof(C11A)=Sof(H11A)=Sof(C1A)=Sof(H1A)=Sof(C9A)=
 Sof(H9A)=Sof(C18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)=Sof(N1A)=Sof(N2A)=
 FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C10A(H10A), C11A(H11A), C1A(H1A), C9A(H9A), C19A(H19A), C20A(H20A),
 C19B(H19B), C1B(H1B), C20B(H20B), C11B(H11B), C9B(H9B), C10B(H10B), C3(H3),
 C6(H6), C16(H16), C13(H13), C4(H4), C7(H7), C17(H17), C14(H14)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C10A C 0.8437(3) 0.5273(4) 0.76217(5) 0.0196(4) Uani 0.946(3) 1 d . . P A 1
H10A H 0.9090 0.6582 0.7712 0.024 Uiso 0.946(3) 1 calc R . P A 1
C8A C 0.6750(3) 0.3241(3) 0.71162(5) 0.0190(4) Uani 0.946(3) 1 d . . P A 1
C11A C 0.8846(3) 0.3407(4) 0.82513(5) 0.0197(4) Uani 0.946(3) 1 d . . P A 1
H11A H 0.8878 0.1996 0.8383 0.024 Uiso 0.946(3) 1 calc R . P A 1
C1A C 0.5927(3) 0.3206(4) 0.67318(5) 0.0200(4) Uani 0.946(3) 1 d . . P A 1
H1A H 0.5516 0.1782 0.6629 0.024 Uiso 0.946(3) 1 calc R . P A 1
C9A C 0.7739(3) 0.5218(4) 0.72559(6) 0.0197(4) Uani 0.946(3) 1 d . . P A 1
H9A H 0.7920 0.6488 0.7101 0.024 Uiso 0.946(3) 1 calc R . P A 1
C18A C 0.8169(3) 0.3369(4) 0.78598(5) 0.0190(4) Uani 0.946(3) 1 d . . P A 1
C19A C 0.7230(3) 0.1384(4) 0.77182(5) 0.0191(4) Uani 0.946(3) 1 d . . P A 1
H19A H 0.7073 0.0098 0.7872 0.023 Uiso 0.946(3) 1 calc R . P A 1
C20A C 0.6528(3) 0.1323(4) 0.73487(5) 0.0211(4) Uani 0.946(3) 1 d . . P A 1
H20A H 0.5907 -0.0005 0.7256 0.025 Uiso 0.946(3) 1 calc R . P A 1
N1A N 0.5761(2) 0.5053(3) 0.65372(5) 0.0218(4) Uani 0.946(3) 1 d . . P A 1
N2A N 0.9393(2) 0.5261(3) 0.84225(5) 0.0225(4) Uani 0.946(3) 1 d . . P A 1
C19B C 0.726(5) 0.481(5) 0.7749(8) 0.0191(4) Uani 0.054(3) 1 d D . P A 2
H19B H 0.7164 0.3508 0.7902 0.023 Uiso 0.054(3) 1 calc R . P A 2
C1B C 0.902(5) 0.688(7) 0.8258(7) 0.0197(4) Uani 0.054(3) 1 d D . P A 2
H1B H 0.9253 0.8331 0.8371 0.024 Uiso 0.054(3) 1 calc R . P A 2
C20B C 0.651(5) 0.483(5) 0.7383(7) 0.0211(4) Uani 0.054(3) 1 d D . P A 2
H20B H 0.5868 0.3502 0.7296 0.025 Uiso 0.054(3) 1 calc R . P A 2
C11B C 0.613(5) 0.658(7) 0.6731(7) 0.0200(4) Uani 0.054(3) 1 d D . P A 2
H11B H 0.6113 0.8036 0.6613 0.024 Uiso 0.054(3) 1 calc R . P A 2
C18B C 0.818(4) 0.686(5) 0.7877(7) 0.0190(4) Uani 0.054(3) 1 d D . P A 2
C8B C 0.664(4) 0.671(5) 0.7136(7) 0.0190(4) Uani 0.054(3) 1 d D . P A 2
C9B C 0.778(4) 0.850(6) 0.7273(8) 0.0197(4) Uani 0.054(3) 1 d D . P A 2
H9B H 0.8115 0.9632 0.7105 0.024 Uiso 0.054(3) 1 calc R . P A 2
C10B C 0.848(5) 0.874(5) 0.7643(7) 0.0196(4) Uani 0.054(3) 1 d D . P A 2
H10B H 0.9101 1.0083 0.7727 0.024 Uiso 0.054(3) 1 calc R . P A 2
N1B N 0.5761(2) 0.5053(3) 0.65372(5) 0.0218(4) Uani 0.054(3) 1 d . . P A 2
N2B N 0.9393(2) 0.5261(3) 0.84225(5) 0.0225(4) Uani 0.054(3) 1 d . . P A 2
F2 F 1.20219(17) 0.4933(2) 0.99027(3) 0.0267(3) Uani 1 1 d . . . . .
F1 F 0.28202(18) 0.5063(2) 0.50778(3) 0.0281(3) Uani 1 1 d . . . . .
C5 C 0.3529(3) 0.5032(3) 0.54372(5) 0.0195(4) Uani 1 1 d . . . . .
C2 C 0.5001(3) 0.4960(3) 0.61652(5) 0.0188(4) Uani 1 1 d . . . . .
C12 C 1.0081(3) 0.5122(3) 0.87991(5) 0.0182(4) Uani 1 1 d . . . . .
C15 C 1.1373(3) 0.4981(3) 0.95385(5) 0.0198(4) Uani 1 1 d . . . . .
C3 C 0.5314(3) 0.3081(3) 0.59254(5) 0.0207(4) Uani 1 1 d . . . . .
H3 H 0.6015 0.1807 0.6013 0.025 Uiso 1 1 calc R . . . .
C6 C 0.3197(3) 0.6907(3) 0.56644(5) 0.0200(4) Uani 1 1 d . . . . .
H6 H 0.2477 0.8160 0.5575 0.024 Uiso 1 1 calc R . . . .
C16 C 1.1784(3) 0.3138(3) 0.93127(5) 0.0204(4) Uani 1 1 d . . . . .
H16 H 1.2484 0.1879 0.9407 0.024 Uiso 1 1 calc R . . . .
C13 C 0.9713(3) 0.6972(3) 0.90380(5) 0.0212(4) Uani 1 1 d . . . . .
H13 H 0.9038 0.8259 0.8946 0.025 Uiso 1 1 calc R . . . .
C4 C 0.4583(3) 0.3113(3) 0.55587(5) 0.0208(4) Uani 1 1 d . . . . .
H4 H 0.4793 0.1881 0.5398 0.025 Uiso 1 1 calc R . . . .
C7 C 0.3957(3) 0.6887(3) 0.60282(5) 0.0201(4) Uani 1 1 d . . . . .
H7 H 0.3776 0.8159 0.6183 0.024 Uiso 1 1 calc R . . . .
C17 C 1.1128(3) 0.3206(3) 0.89403(5) 0.0193(4) Uani 1 1 d . . . . .
H17 H 1.1384 0.1974 0.8783 0.023 Uiso 1 1 calc R . . . .
C14 C 1.0346(3) 0.6900(3) 0.94106(5) 0.0205(4) Uani 1 1 d . . . . .
H14 H 1.0088 0.8112 0.9571 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
C10A H10A 0.9300 . ?
C10A C9A 1.376(3) . ?
C10A C18A 1.405(3) . ?
C8A C1A 1.466(3) . ?
C8A C9A 1.409(3) . ?
C8A C20A 1.393(3) . ?
C11A H11A 0.9300 . ?
C11A C18A 1.457(3) . ?
C11A N2A 1.268(3) . ?
C1A H1A 0.9300 . ?
C1A N1A 1.261(3) . ?
C9A H9A 0.9300 . ?
C18A C19A 1.398(3) . ?
C19A H19A 0.9300 . ?
C19A C20A 1.389(3) . ?
C20A H20A 0.9300 . ?
N1A C2 1.411(2) . ?
N2A C12 1.412(2) . ?
C19B H19B 0.9300 . ?
C19B C20B 1.391(19) . ?
C19B C18B 1.408(19) . ?
C1B H1B 0.9300 . ?
C1B C18B 1.455(18) . ?
C1B N2B 1.11(3) . ?
C20B H20B 0.9300 . ?
C20B C8B 1.396(19) . ?
C11B H11B 0.9300 . ?
C11B C8B 1.479(18) . ?
C11B N1B 1.13(3) . ?
C18B C10B 1.389(19) . ?
C8B C9B 1.390(19) . ?
C9B H9B 0.9300 . ?
C9B C10B 1.393(19) . ?
C10B H10B 0.9300 . ?
N1B C2 1.411(2) . ?
N2B C12 1.412(2) . ?
F2 C15 1.360(2) . ?
F1 C5 1.356(2) . ?
C5 C6 1.379(3) . ?
C5 C4 1.389(3) . ?
C2 C3 1.405(3) . ?
C2 C7 1.405(3) . ?
C12 C13 1.400(3) . ?
C12 C17 1.406(3) . ?
C15 C16 1.376(3) . ?
C15 C14 1.385(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.386(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.383(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.389(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.386(2) . ?
C4 H4 0.9300 . ?
C7 H7 0.9300 . ?
C17 H17 0.9300 . ?
C14 H14 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9A C10A H10A 119.7 . . ?
C9A C10A C18A 120.50(18) . . ?
C18A C10A H10A 119.7 . . ?
C9A C8A C1A 120.70(17) . . ?
C20A C8A C1A 119.85(18) . . ?
C20A C8A C9A 119.44(18) . . ?
C18A C11A H11A 118.2 . . ?
N2A C11A H11A 118.2 . . ?
N2A C11A C18A 123.58(18) . . ?
C8A C1A H1A 119.1 . . ?
N1A C1A C8A 121.86(18) . . ?
N1A C1A H1A 119.1 . . ?
C10A C9A C8A 120.17(18) . . ?
C10A C9A H9A 119.9 . . ?
C8A C9A H9A 119.9 . . ?
C10A C18A C11A 121.74(18) . . ?
C19A C18A C10A 119.24(18) . . ?
C19A C18A C11A 119.02(18) . . ?
C18A C19A H19A 119.9 . . ?
C20A C19A C18A 120.29(18) . . ?
C20A C19A H19A 119.9 . . ?
C8A C20A H20A 119.8 . . ?
C19A C20A C8A 120.31(19) . . ?
C19A C20A H20A 119.8 . . ?
C1A N1A C2 120.69(17) . . ?
C11A N2A C12 119.75(17) . . ?
C20B C19B H19B 121.6 . . ?
C20B C19B C18B 117(3) . . ?
C18B C19B H19B 121.6 . . ?
C18B C1B H1B 117.8 . . ?
N2B C1B H1B 117.8 . . ?
N2B C1B C18B 124(3) . . ?
C19B C20B H20B 117.7 . . ?
C19B C20B C8B 125(3) . . ?
C8B C20B H20B 117.7 . . ?
C8B C11B H11B 113.8 . . ?
N1B C11B H11B 113.8 . . ?
N1B C11B C8B 132(3) . . ?
C19B C18B C1B 118(2) . . ?
C10B C18B C19B 122(2) . . ?
C10B C18B C1B 120(2) . . ?
C20B C8B C11B 125(2) . . ?
C9B C8B C20B 114(3) . . ?
C9B C8B C11B 119(2) . . ?
C8B C9B H9B 117.5 . . ?
C8B C9B C10B 125(3) . . ?
C10B C9B H9B 117.5 . . ?
C18B C10B C9B 116(3) . . ?
C18B C10B H10B 121.8 . . ?
C9B C10B H10B 121.8 . . ?
C11B N1B C2 132.2(17) . . ?
C1B N2B C12 127.7(16) . . ?
F1 C5 C6 118.93(16) . . ?
F1 C5 C4 118.24(17) . . ?
C6 C5 C4 122.82(17) . . ?
C3 C2 N1A 122.72(17) . . ?
C3 C2 N1B 122.72(17) . . ?
C7 C2 N1A 117.91(17) . . ?
C7 C2 N1B 117.91(17) . . ?
C7 C2 C3 119.31(17) . . ?
C13 C12 N2A 118.51(17) . . ?
C13 C12 N2B 118.51(17) . . ?
C13 C12 C17 119.19(17) . . ?
C17 C12 N2A 122.30(17) . . ?
C17 C12 N2B 122.30(17) . . ?
F2 C15 C16 118.62(16) . . ?
F2 C15 C14 118.42(17) . . ?
C16 C15 C14 122.96(17) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.41(18) . . ?
C4 C3 H3 119.8 . . ?
C5 C6 H6 120.7 . . ?
C5 C6 C7 118.62(18) . . ?
C7 C6 H6 120.7 . . ?
C15 C16 H16 120.8 . . ?
C15 C16 C17 118.34(17) . . ?
C17 C16 H16 120.8 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.49(18) . . ?
C14 C13 H13 119.8 . . ?
C5 C4 H4 120.8 . . ?
C3 C4 C5 118.33(17) . . ?
C3 C4 H4 120.8 . . ?
C2 C7 H7 119.8 . . ?
C6 C7 C2 120.47(18) . . ?
C6 C7 H7 119.8 . . ?
C12 C17 H17 119.7 . . ?
C16 C17 C12 120.54(17) . . ?
C16 C17 H17 119.7 . . ?
C15 C14 C13 118.48(17) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10A C18A C19A C20A -1.7(3) . . . . ?
C8A C1A N1A C2 178.51(17) . . . . ?
C11A C18A C19A C20A 178.31(18) . . . . ?
C11A N2A C12 C13 -143.5(2) . . . . ?
C11A N2A C12 C17 37.0(3) . . . . ?
C1A C8A C9A C10A 177.10(18) . . . . ?
C1A C8A C20A C19A -176.94(18) . . . . ?
C1A N1A C2 C3 -37.2(3) . . . . ?
C1A N1A C2 C7 145.7(2) . . . . ?
C9A C10A C18A C11A -178.14(18) . . . . ?
C9A C10A C18A C19A 1.8(3) . . . . ?
C9A C8A C1A N1A -14.0(3) . . . . ?
C9A C8A C20A C19A 1.9(3) . . . . ?
C18A C10A C9A C8A -0.2(3) . . . . ?
C18A C11A N2A C12 -177.99(18) . . . . ?
C18A C19A C20A C8A -0.2(3) . . . . ?
C20A C8A C1A N1A 164.8(2) . . . . ?
C20A C8A C9A C10A -1.7(3) . . . . ?
N1A C2 C3 C4 -177.86(18) . . . . ?
N1A C2 C7 C6 179.22(17) . . . . ?
N2A C11A C18A C10A 14.2(3) . . . . ?
N2A C11A C18A C19A -165.8(2) . . . . ?
N2A C12 C13 C14 179.39(18) . . . . ?
N2A C12 C17 C16 179.84(17) . . . . ?
C19B C20B C8B C11B 168(3) . . . . ?
C19B C20B C8B C9B 7(5) . . . . ?
C19B C18B C10B C9B 1(5) . . . . ?
C1B C18B C10B C9B 174(3) . . . . ?
C1B N2B C12 C13 24(2) . . . . ?
C1B N2B C12 C17 -155(2) . . . . ?
C20B C19B C18B C1B -179(3) . . . . ?
C20B C19B C18B C10B -6(5) . . . . ?
C20B C8B C9B C10B -13(5) . . . . ?
C11B C8B C9B C10B -175(3) . . . . ?
C11B N1B C2 C3 153(2) . . . . ?
C11B N1B C2 C7 -24(2) . . . . ?
C18B C19B C20B C8B 1(6) . . . . ?
C18B C1B N2B C12 -175(2) . . . . ?
C8B C11B N1B C2 168(3) . . . . ?
C8B C9B C10B C18B 9(5) . . . . ?
N1B C11B C8B C20B -10(6) . . . . ?
N1B C11B C8B C9B 151(4) . . . . ?
N1B C2 C3 C4 -177.86(18) . . . . ?
N1B C2 C7 C6 179.22(17) . . . . ?
N2B C1B C18B C19B 22(5) . . . . ?
N2B C1B C18B C10B -152(4) . . . . ?
N2B C12 C13 C14 179.39(18) . . . . ?
N2B C12 C17 C16 179.84(17) . . . . ?
F2 C15 C16 C17 -179.54(17) . . . . ?
F2 C15 C14 C13 178.81(17) . . . . ?
F1 C5 C6 C7 -178.61(17) . . . . ?
F1 C5 C4 C3 179.81(17) . . . . ?
C5 C6 C7 C2 -1.8(3) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C12 C13 C14 C15 1.1(3) . . . . ?
C15 C16 C17 C12 0.4(3) . . . . ?
C3 C2 C7 C6 2.0(3) . . . . ?
C6 C5 C4 C3 0.7(3) . . . . ?
C16 C15 C14 C13 -0.3(3) . . . . ?
C13 C12 C17 C16 0.3(3) . . . . ?
C4 C5 C6 C7 0.5(3) . . . . ?
C7 C2 C3 C4 -0.7(3) . . . . ?
C17 C12 C13 C14 -1.1(3) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.323
_oxdiff_exptl_absorpt_empirical_full_min 0.872
####################################################################### 
# 
# 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 1562527'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7CE01872J 2017
_audit_update_record             
;
2017-07-17 deposited with the CCDC.
2018-01-10 downloaded from the CCDC.
;
_audit_creation_date             2016-12-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H12 F4 N2'
_chemical_formula_sum            'C20 H18 F4 N2 '
_chemical_formula_weight         362.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   16.806(5)
_cell_length_b                   6.726(3)
_cell_length_c                   7.298(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.110(16)
_cell_angle_gamma                90
_cell_volume                     814.5(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2076
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing 1995'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7512
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         3.268
_diffrn_ambient_temperature      100.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
scan:
	Number of images: 599
	           Slice: -69.0000 - 110.7000
	     Image width: 0.3000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 0.0000
	             XTD: 49.8600
	          2theta: 29.8900
scan:
	Number of images: 603
	           Slice: -69.0000 - 111.9000
	     Image width: 0.3000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 240.0000
	             XTD: 49.8600
	          2theta: 29.8900
scan:
	Number of images: 506
	           Slice: -32.0000 - 119.8000
	     Image width: 0.3000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 120.0000
	             XTD: 49.8600
	          2theta: 29.8900
;
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.135964
_diffrn_orient_matrix_UB_12      0.023441
_diffrn_orient_matrix_UB_13      0.014941
_diffrn_orient_matrix_UB_21      0.019122
_diffrn_orient_matrix_UB_22      0.017608
_diffrn_orient_matrix_UB_23      0.146385
_diffrn_orient_matrix_UB_31      -0.000211
_diffrn_orient_matrix_UB_32      0.059834
_diffrn_orient_matrix_UB_33      -0.007170
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           12.0
_diffrn_source_power             0.6
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1516
_reflns_number_total             1855
_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       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_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    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1855
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0501
_refine_ls_restrained_S_all      1.096
_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)+(0.0840P)²+0.1002P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1429
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C5(H5), C7(H7), C9(H9), C10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.24383(5) 1.08485(11) 0.16288(13) 0.0309(3) Uani 1 1 d . . . . .
F2 F 0.07086(5) 0.43401(13) -0.09663(13) 0.0314(3) Uani 1 1 d . . . . .
N1 N 0.34460(7) 0.54176(17) 0.29175(16) 0.0213(3) Uani 1 1 d . . . . .
C1 C 0.31594(8) 0.7132(2) 0.24947(19) 0.0203(3) Uani 1 1 d . . . . .
H1 H 0.3466 0.8281 0.2902 0.024 Uiso 1 1 calc R . . . .
C2 C 0.23554(8) 0.7350(2) 0.13775(18) 0.0193(3) Uani 1 1 d . . . . .
C3 C 0.20099(9) 0.92125(19) 0.0972(2) 0.0227(3) Uani 1 1 d . . . . .
C4 C 0.12526(8) 0.9481(2) -0.0045(2) 0.0250(4) Uani 1 1 d . . . . .
H4 H 0.1041 1.0781 -0.0292 0.030 Uiso 1 1 calc R . . . .
C5 C 0.08063(8) 0.7826(2) -0.0698(2) 0.0241(3) Uani 1 1 d . . . . .
H5 H 0.0281 0.7961 -0.1394 0.029 Uiso 1 1 calc R . . . .
C6 C 0.11464(8) 0.5974(2) -0.0309(2) 0.0225(3) Uani 1 1 d . . . . .
C7 C 0.19004(8) 0.5690(2) 0.06973(19) 0.0210(3) Uani 1 1 d . . . . .
H7 H 0.2110 0.4386 0.0928 0.025 Uiso 1 1 calc R . . . .
C8 C 0.42309(8) 0.52593(19) 0.39615(18) 0.0189(3) Uani 1 1 d . . . . .
C9 C 0.43693(8) 0.3763(2) 0.52928(19) 0.0210(3) Uani 1 1 d . . . . .
H9 H 0.3941 0.2907 0.5490 0.025 Uiso 1 1 calc R . . . .
C10 C 0.51288(8) 0.3514(2) 0.63337(19) 0.0205(3) Uani 1 1 d . . . . .
H10 H 0.5215 0.2503 0.7253 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
F1 C3 1.3600(16) . ?
F2 C6 1.3667(16) . ?
N1 C1 1.2687(18) . ?
N1 C8 1.4190(17) . ?
C1 H1 0.9500 . ?
C1 C2 1.4708(18) . ?
C2 C3 1.3928(19) . ?
C2 C7 1.3992(19) . ?
C3 C4 1.380(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.381(2) . ?
C6 C7 1.3737(19) . ?
C7 H7 0.9500 . ?
C8 C9 1.3928(19) . ?
C8 C10 1.3997(18) 3_666 ?
C9 H9 0.9500 . ?
C9 C10 1.3883(19) . ?
C10 C8 1.3997(18) 3_666 ?
C10 H10 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 C8 118.92(11) . . ?
N1 C1 H1 119.8 . . ?
N1 C1 C2 120.36(12) . . ?
C2 C1 H1 119.8 . . ?
C3 C2 C1 121.53(12) . . ?
C3 C2 C7 117.16(12) . . ?
C7 C2 C1 121.31(12) . . ?
F1 C3 C2 118.25(13) . . ?
F1 C3 C4 118.38(12) . . ?
C4 C3 C2 123.37(13) . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 118.90(13) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 H5 121.0 . . ?
C6 C5 C4 118.06(13) . . ?
C6 C5 H5 121.0 . . ?
F2 C6 C5 118.09(12) . . ?
F2 C6 C7 118.38(12) . . ?
C7 C6 C5 123.53(13) . . ?
C2 C7 H7 120.5 . . ?
C6 C7 C2 118.98(12) . . ?
C6 C7 H7 120.5 . . ?
C9 C8 N1 117.85(11) . . ?
C9 C8 C10 119.08(12) . 3_666 ?
C10 C8 N1 123.03(12) 3_666 . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.42(12) . . ?
C10 C9 H9 119.8 . . ?
C8 C10 H10 119.8 3_666 . ?
C9 C10 C8 120.49(12) . 3_666 ?
C9 C10 H10 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C3 C4 C5 -179.10(12) . . . . ?
F2 C6 C7 C2 179.96(12) . . . . ?
N1 C1 C2 C3 176.75(13) . . . . ?
N1 C1 C2 C7 -2.4(2) . . . . ?
N1 C8 C9 C10 178.86(12) . . . . ?
C1 N1 C8 C9 142.70(13) . . . . ?
C1 N1 C8 C10 -39.59(19) . . . 3_666 ?
C1 C2 C3 F1 0.4(2) . . . . ?
C1 C2 C3 C4 -178.91(12) . . . . ?
C1 C2 C7 C6 178.77(11) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
C3 C2 C7 C6 -0.4(2) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
C4 C5 C6 F2 -179.50(13) . . . . ?
C4 C5 C6 C7 0.3(2) . . . . ?
C5 C6 C7 C2 0.1(2) . . . . ?
C7 C2 C3 F1 179.55(12) . . . . ?
C7 C2 C3 C4 0.3(2) . . . . ?
C8 N1 C1 C2 178.60(11) . . . . ?
C8 C9 C10 C8 -1.1(2) . . . 3_666 ?
C10 C8 C9 C10 1.1(2) 3_666 . . . ?

_shelx_SHELXL_version_number     2014/7
_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_6
_database_code_depnum_ccdc_archive 'CCDC 1562535'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7CE01872J 2017
_audit_update_record             
;
2017-07-17 deposited with the CCDC.
2018-01-10 downloaded from the CCDC.
;
_audit_creation_date             2017-07-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H12 F4 N2'
_chemical_formula_sum            'C20 H12 F4 N2'
_chemical_formula_weight         356.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   4.5664(15)
_cell_length_b                   11.438(3)
_cell_length_c                   14.923(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.382(13)
_cell_angle_gamma                90
_cell_volume                     774.6(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2121
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.2
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessings, 1995'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6663
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.510
_diffrn_reflns_theta_min         2.249
_diffrn_ambient_temperature      100
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
scan:
	Number of images: 600
	           Slice: -69.0000 - 111.0000
	     Image width: 0.3000
	        Exp time: 22.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 120.0000
	             XTD: 49.8600
	          2theta: 29.8900
scan:
	Number of images: 600
	           Slice: -69.0000 - 111.0000
	     Image width: 0.3000
	        Exp time: 22.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 240.0000
	             XTD: 49.8600
	          2theta: 29.8900
scan:
	Number of images: 600
	           Slice: -69.0000 - 111.0000
	     Image width: 0.3000
	        Exp time: 22.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 0.0000
	             XTD: 49.8600
	          2theta: 29.8900
;
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Cryo loop'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.026182
_diffrn_orient_matrix_UB_12      -0.080470
_diffrn_orient_matrix_UB_13      0.203461
_diffrn_orient_matrix_UB_21      0.045326
_diffrn_orient_matrix_UB_22      0.071334
_diffrn_orient_matrix_UB_23      0.022381
_diffrn_orient_matrix_UB_31      -0.055856
_diffrn_orient_matrix_UB_32      0.027301
_diffrn_orient_matrix_UB_33      0.026103
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           12.0
_diffrn_source_power             0.6
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1470
_reflns_number_total             1731
_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       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_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         0.284
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1731
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0437
_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)+(0.0771P)²+0.2164P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1269
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C6(H6), C9(H9), C1(H1), C4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.78641(19) 0.62442(7) 0.83858(6) 0.0284(3) Uani 1 1 d . . . . .
F2 F 1.47181(19) 0.34257(8) 0.95231(6) 0.0290(3) Uani 1 1 d . . . . .
N1 N 0.5849(2) 0.49194(10) 0.69439(8) 0.0201(3) Uani 1 1 d . . . . .
C7 C 0.9263(3) 0.33385(12) 0.75813(9) 0.0206(3) Uani 1 1 d . . . . .
H7 H 0.8585 0.2826 0.7121 0.025 Uiso 1 1 calc R . . . .
C5 C 1.2485(3) 0.37539(12) 0.88961(9) 0.0219(3) Uani 1 1 d . . . . .
C2 C 0.7993(3) 0.44509(11) 0.76001(9) 0.0184(3) Uani 1 1 d . . . . .
C10 C -0.0448(3) 0.61821(11) 0.48387(9) 0.0204(3) Uani 1 1 d . . . . .
H10 H -0.0751 0.6976 0.4729 0.025 Uiso 1 1 calc R . . . .
C8 C 0.2116(3) 0.46408(11) 0.56944(9) 0.0186(3) Uani 1 1 d . . . . .
C6 C 1.1494(3) 0.29755(12) 0.82249(9) 0.0217(3) Uani 1 1 d . . . . .
H6 H 1.2298 0.2230 0.8205 0.026 Uiso 1 1 calc R . . . .
C3 C 0.9084(3) 0.51744(11) 0.83133(9) 0.0207(3) Uani 1 1 d . . . . .
C9 C 0.1639(3) 0.58281(11) 0.55251(9) 0.0204(3) Uani 1 1 d . . . . .
H9 H 0.2729 0.6382 0.5875 0.025 Uiso 1 1 calc R . . . .
C1 C 0.4302(3) 0.42245(11) 0.64147(9) 0.0194(3) Uani 1 1 d . . . . .
H1 H 0.4575 0.3423 0.6490 0.023 Uiso 1 1 calc R . . . .
C4 C 1.1332(3) 0.48583(12) 0.89606(9) 0.0230(3) Uani 1 1 d . . . . .
H4 H 1.2038 0.5368 0.9420 0.028 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C3 1.3538(15) . ?
F2 C5 1.3581(15) . ?
N1 C2 1.4113(16) . ?
N1 C1 1.2770(17) . ?
C7 H7 0.9300 . ?
C7 C2 1.3999(18) . ?
C7 C6 1.3837(18) . ?
C5 C6 1.3784(19) . ?
C5 C4 1.376(2) . ?
C2 C3 1.3956(19) . ?
C10 H10 0.9300 . ?
C10 C8 1.4014(18) 3_566 ?
C10 C9 1.3799(18) . ?
C8 C10 1.4014(18) 3_566 ?
C8 C9 1.3941(19) . ?
C8 C1 1.4629(18) . ?
C6 H6 0.9300 . ?
C3 C4 1.3773(19) . ?
C9 H9 0.9300 . ?
C1 H1 0.9300 . ?
C4 H4 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 119.10(12) . . ?
C2 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C6 C7 C2 122.24(12) . . ?
F2 C5 C6 118.88(12) . . ?
F2 C5 C4 117.99(12) . . ?
C4 C5 C6 123.12(13) . . ?
C7 C2 N1 126.03(12) . . ?
C3 C2 N1 117.73(12) . . ?
C3 C2 C7 116.15(12) . . ?
C8 C10 H10 119.6 3_566 . ?
C9 C10 H10 119.6 . . ?
C9 C10 C8 120.74(12) . 3_566 ?
C10 C8 C1 118.81(12) 3_566 . ?
C9 C8 C10 119.16(12) . 3_566 ?
C9 C8 C1 122.03(12) . . ?
C7 C6 H6 121.1 . . ?
C5 C6 C7 117.87(13) . . ?
C5 C6 H6 121.1 . . ?
F1 C3 C2 118.80(12) . . ?
F1 C3 C4 117.54(12) . . ?
C4 C3 C2 123.65(12) . . ?
C10 C9 C8 120.09(12) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
N1 C1 C8 122.50(12) . . ?
N1 C1 H1 118.7 . . ?
C8 C1 H1 118.7 . . ?
C5 C4 C3 116.94(13) . . ?
C5 C4 H4 121.5 . . ?
C3 C4 H4 121.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C3 C4 C5 177.88(12) . . . . ?
F2 C5 C6 C7 -178.52(12) . . . . ?
F2 C5 C4 C3 179.53(12) . . . . ?
N1 C2 C3 F1 5.71(19) . . . . ?
N1 C2 C3 C4 -174.98(13) . . . . ?
C7 C2 C3 F1 -177.55(12) . . . . ?
C7 C2 C3 C4 1.8(2) . . . . ?
C2 N1 C1 C8 -177.57(11) . . . . ?
C2 C7 C6 C5 -0.7(2) . . . . ?
C2 C3 C4 C5 -1.4(2) . . . . ?
C10 C8 C9 C10 -0.1(2) 3_566 . . . ?
C10 C8 C1 N1 -178.08(13) 3_566 . . . ?
C8 C10 C9 C8 0.1(2) 3_566 . . . ?
C6 C7 C2 N1 175.77(12) . . . . ?
C6 C7 C2 C3 -0.7(2) . . . . ?
C6 C5 C4 C3 0.0(2) . . . . ?
C9 C8 C1 N1 1.7(2) . . . . ?
C1 N1 C2 C7 20.4(2) . . . . ?
C1 N1 C2 C3 -163.21(13) . . . . ?
C1 C8 C9 C10 -179.96(12) . . . . ?
C4 C5 C6 C7 1.0(2) . . . . ?

_olex2_exptl_crystal_mounting_method 'cryo loop'
_olex2_submission_special_instructions 'No special instructions were received'
