# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_4A
_database_code_depnum_ccdc_archive 'CCDC 1585036'
_audit_update_record             
;
2017-11-10 deposited with the CCDC.
2018-03-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H9 F6 N'
_chemical_formula_sum            'C19 H9 F6 N'
_chemical_formula_weight         365.27

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.08220(10)
_cell_length_b                   15.6783(2)
_cell_length_c                   14.5087(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.9680(10)
_cell_angle_gamma                90
_cell_volume                     1599.10(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9961
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      28.24

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.138
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.936
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25426
_diffrn_reflns_av_unetI/netI     0.0117
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.920
_diffrn_reflns_theta_max         28.278
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3962
_reflns_number_gt                3481
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT-plus (Bruker, 2008)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2008)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 2012)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0557P)²+1.1729P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3962
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1232
_refine_ls_wR_factor_gt          0.1180
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C3 C 0.36129(19) 0.55092(9) 0.62147(9) 0.0182(3) Uani 1 1 d . . . . .
C2 C 0.4025(2) 0.52717(9) 0.71339(9) 0.0205(3) Uani 1 1 d . . . . .
H2 H 0.3921 0.4694 0.7318 0.025 Uiso 1 1 calc R U . . .
C1 C 0.4601(2) 0.59061(9) 0.77870(9) 0.0201(3) Uani 1 1 d . . . . .
C9 C 0.44370(18) 0.69649(9) 0.67043(9) 0.0178(3) Uani 1 1 d . . . . .
C4 C 0.38391(19) 0.63822(9) 0.59757(9) 0.0178(3) Uani 1 1 d . . . . .
C5 C 0.3465(2) 0.66782(9) 0.50496(9) 0.0213(3) Uani 1 1 d . . . . .
H5 H 0.3074 0.6287 0.4563 0.026 Uiso 1 1 calc R U . . .
C6 C 0.3664(2) 0.75227(10) 0.48515(10) 0.0246(3) Uani 1 1 d . . . . .
H6 H 0.3422 0.7716 0.4228 0.030 Uiso 1 1 calc R U . . .
C7 C 0.4229(2) 0.81101(9) 0.55704(10) 0.0244(3) Uani 1 1 d . . . . .
H7 H 0.4353 0.8697 0.5426 0.029 Uiso 1 1 calc R U . . .
C8 C 0.4603(2) 0.78441(9) 0.64760(10) 0.0205(3) Uani 1 1 d . . . . .
C11 C 0.5094(2) 0.84907(9) 0.72309(10) 0.0244(3) Uani 1 1 d . . . . .
C10 C 0.5034(2) 0.56596(10) 0.87999(10) 0.0276(3) Uani 1 1 d . . . . .
C12 C 0.2909(2) 0.49009(9) 0.55264(10) 0.0202(3) Uani 1 1 d . . . . .
C13 C 0.22461(19) 0.44006(9) 0.49525(10) 0.0202(3) Uani 1 1 d . . . . .
C14 C 0.14736(19) 0.38265(9) 0.42366(9) 0.0192(3) Uani 1 1 d . . . . .
C15 C 0.1138(2) 0.29697(9) 0.44317(10) 0.0229(3) Uani 1 1 d . . . . .
H15 H 0.1411 0.2760 0.5048 0.027 Uiso 1 1 calc R U . . .
C16 C 0.0405(2) 0.24272(10) 0.37204(11) 0.0275(3) Uani 1 1 d . . . . .
H16 H 0.0184 0.1844 0.3850 0.033 Uiso 1 1 calc R U . . .
C17 C -0.0008(2) 0.27345(11) 0.28203(11) 0.0283(3) Uani 1 1 d . . . . .
H17 H -0.0515 0.2361 0.2337 0.034 Uiso 1 1 calc R U . . .
C18 C 0.0315(2) 0.35830(11) 0.26240(10) 0.0268(3) Uani 1 1 d . . . . .
H18 H 0.0028 0.3790 0.2008 0.032 Uiso 1 1 calc R U . . .
C19 C 0.1057(2) 0.41301(9) 0.33273(10) 0.0226(3) Uani 1 1 d . . . . .
H19 H 0.1284 0.4711 0.3192 0.027 Uiso 1 1 calc R U . . .
N1 N 0.48064(17) 0.67211(8) 0.76108(8) 0.0193(2) Uani 1 1 d . . . . .
F4 F 0.51536(18) 0.92835(6) 0.68818(7) 0.0417(3) Uani 1 1 d . . . . .
F5 F 0.67808(13) 0.83619(6) 0.77343(7) 0.0310(2) Uani 1 1 d . . . . .
F6 F 0.38064(14) 0.85184(6) 0.78361(7) 0.0331(2) Uani 1 1 d . . . . .
F1 F 0.4432(3) 0.62213(8) 0.93611(8) 0.0693(5) Uani 1 1 d . . . . .
F2 F 0.69114(19) 0.55895(10) 0.90504(8) 0.0599(4) Uani 1 1 d . . . . .
F3 F 0.4313(2) 0.49080(7) 0.89759(7) 0.0502(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
C3 C2 1.3813(19) . ?
C3 C4 1.4257(19) . ?
C3 C12 1.4264(19) . ?
C2 C1 1.4000(19) . ?
C2 H2 0.9500 . ?
C1 N1 1.3146(18) . ?
C1 C10 1.5145(19) . ?
C9 N1 1.3641(17) . ?
C9 C4 1.4223(18) . ?
C9 C8 1.4258(19) . ?
C4 C5 1.4158(18) . ?
C5 C6 1.366(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.413(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.3732(19) . ?
C7 H7 0.9500 . ?
C8 C11 1.5020(19) . ?
C11 F5 1.3379(18) . ?
C11 F6 1.3410(18) . ?
C11 F4 1.3448(17) . ?
C10 F1 1.306(2) . ?
C10 F3 1.3214(18) . ?
C10 F2 1.340(2) . ?
C12 C13 1.198(2) . ?
C13 C14 1.4320(19) . ?
C14 C15 1.399(2) . ?
C14 C19 1.3997(19) . ?
C15 C16 1.389(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.389(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.385(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.387(2) . ?
C18 H18 0.9500 . ?
C19 H19 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
C2 C3 C4 118.47(12) . . ?
C2 C3 C12 120.71(13) . . ?
C4 C3 C12 120.78(12) . . ?
C3 C2 C1 118.17(13) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
N1 C1 C2 126.08(13) . . ?
N1 C1 C10 115.00(12) . . ?
C2 C1 C10 118.92(13) . . ?
N1 C9 C4 122.79(12) . . ?
N1 C9 C8 118.90(12) . . ?
C4 C9 C8 118.28(12) . . ?
C5 C4 C9 119.96(12) . . ?
C5 C4 C3 122.13(12) . . ?
C9 C4 C3 117.91(12) . . ?
C6 C5 C4 120.36(13) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 120.25(13) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 120.86(13) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 120.28(13) . . ?
C7 C8 C11 119.56(13) . . ?
C9 C8 C11 120.09(12) . . ?
F5 C11 F6 106.29(12) . . ?
F5 C11 F4 106.16(13) . . ?
F6 C11 F4 105.76(12) . . ?
F5 C11 C8 114.12(12) . . ?
F6 C11 C8 112.56(12) . . ?
F4 C11 C8 111.36(12) . . ?
F1 C10 F3 108.54(15) . . ?
F1 C10 F2 105.94(15) . . ?
F3 C10 F2 105.57(14) . . ?
F1 C10 C1 112.96(13) . . ?
F3 C10 C1 112.18(12) . . ?
F2 C10 C1 111.19(13) . . ?
C13 C12 C3 177.40(15) . . ?
C12 C13 C14 177.59(15) . . ?
C15 C14 C19 119.72(13) . . ?
C15 C14 C13 121.06(13) . . ?
C19 C14 C13 119.22(13) . . ?
C16 C15 C14 119.67(14) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 120.22(14) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 120.34(14) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 120.00(14) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C14 120.05(14) . . ?
C18 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?
C1 N1 C9 116.56(12) . . ?

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
C4 C3 C2 C1 1.5(2) . . . . ?
C12 C3 C2 C1 -176.17(13) . . . . ?
C3 C2 C1 N1 -0.5(2) . . . . ?
C3 C2 C1 C10 179.18(13) . . . . ?
N1 C9 C4 C5 179.52(12) . . . . ?
C8 C9 C4 C5 1.33(19) . . . . ?
N1 C9 C4 C3 0.34(19) . . . . ?
C8 C9 C4 C3 -177.85(12) . . . . ?
C2 C3 C4 C5 179.40(13) . . . . ?
C12 C3 C4 C5 -2.9(2) . . . . ?
C2 C3 C4 C9 -1.44(19) . . . . ?
C12 C3 C4 C9 176.24(12) . . . . ?
C9 C4 C5 C6 -0.4(2) . . . . ?
C3 C4 C5 C6 178.74(13) . . . . ?
C4 C5 C6 C7 -0.6(2) . . . . ?
C5 C6 C7 C8 0.6(2) . . . . ?
C6 C7 C8 C9 0.4(2) . . . . ?
C6 C7 C8 C11 -176.57(14) . . . . ?
N1 C9 C8 C7 -179.60(13) . . . . ?
C4 C9 C8 C7 -1.3(2) . . . . ?
N1 C9 C8 C11 -2.6(2) . . . . ?
C4 C9 C8 C11 175.63(12) . . . . ?
C7 C8 C11 F5 -122.13(15) . . . . ?
C9 C8 C11 F5 60.88(18) . . . . ?
C7 C8 C11 F6 116.61(15) . . . . ?
C9 C8 C11 F6 -60.38(17) . . . . ?
C7 C8 C11 F4 -2.0(2) . . . . ?
C9 C8 C11 F4 -178.96(13) . . . . ?
N1 C1 C10 F1 39.2(2) . . . . ?
C2 C1 C10 F1 -140.54(16) . . . . ?
N1 C1 C10 F3 162.24(14) . . . . ?
C2 C1 C10 F3 -17.5(2) . . . . ?
N1 C1 C10 F2 -79.79(17) . . . . ?
C2 C1 C10 F2 100.49(16) . . . . ?
C19 C14 C15 C16 0.3(2) . . . . ?
C13 C14 C15 C16 -179.40(13) . . . . ?
C14 C15 C16 C17 -0.5(2) . . . . ?
C15 C16 C17 C18 0.2(2) . . . . ?
C16 C17 C18 C19 0.1(2) . . . . ?
C17 C18 C19 C14 -0.3(2) . . . . ?
C15 C14 C19 C18 0.0(2) . . . . ?
C13 C14 C19 C18 179.77(13) . . . . ?
C2 C1 N1 C9 -0.6(2) . . . . ?
C10 C1 N1 C9 179.69(12) . . . . ?
C4 C9 N1 C1 0.67(19) . . . . ?
C8 C9 N1 C1 178.85(13) . . . . ?

_refine_diff_density_max         0.885
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.053

_shelxl_version_number           2014-3

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform'
####################################################################### 
# 
# 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_4B
_database_code_depnum_ccdc_archive 'CCDC 1585037'
_audit_update_record             
;
2017-11-10 deposited with the CCDC.
2018-03-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H11 F6 N'
_chemical_formula_sum            'C20 H11 F6 N'
_chemical_formula_weight         379.30

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.1227(3)
_cell_length_b                   15.8558(3)
_cell_length_c                   14.7066(3)
_cell_angle_alpha                90
_cell_angle_beta                 111.4840(10)
_cell_angle_gamma                90
_cell_volume                     3281.37(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9901
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      27.75
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_F_000             1536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.138
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.958
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            60507
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.935
_diffrn_reflns_theta_max         28.365
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7960
_reflns_number_gt                5541
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT-plus (Bruker, 2008)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2008)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 2012)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0419P)²+1.6426P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7960
_refine_ls_number_parameters     489
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.1043
_refine_ls_wR_factor_gt          0.0897
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F4 F -0.04488(6) 0.54605(6) 0.77928(7) 0.0273(2) Uani 1 1 d . . . . .
F5 F 0.00600(7) 0.56192(6) 0.93524(7) 0.0264(2) Uani 1 1 d . . . . .
F6 F 0.06463(7) 0.46481(5) 0.87212(7) 0.0270(2) Uani 1 1 d . . . . .
F1 F -0.16391(7) 0.78233(6) 0.84283(8) 0.0348(3) Uani 1 1 d . . . . .
F3 F -0.12793(8) 0.90758(6) 0.81623(10) 0.0465(3) Uani 1 1 d . . . . .
F2 F -0.17020(7) 0.81798(9) 0.70041(8) 0.0491(3) Uani 1 1 d . . . . .
F11 F 0.49115(7) 0.32122(6) 0.03558(7) 0.0303(2) Uani 1 1 d . . . . .
F10 F 0.52450(7) 0.29684(6) 0.18797(7) 0.0320(2) Uani 1 1 d . . . . .
F12 F 0.41682(7) 0.22441(6) 0.08038(9) 0.0370(3) Uani 1 1 d . . . . .
F8 F 0.64251(7) 0.56624(6) 0.10904(8) 0.0321(2) Uani 1 1 d . . . . .
F7 F 0.62700(8) 0.66402(7) 0.20281(10) 0.0491(3) Uani 1 1 d . . . . .
F9 F 0.66711(7) 0.53875(8) 0.25817(8) 0.0406(3) Uani 1 1 d . . . . .
N1 N -0.00194(9) 0.71898(8) 0.82984(9) 0.0184(3) Uani 1 1 d . . . . .
N2 N 0.49061(9) 0.47774(8) 0.13862(9) 0.0205(3) Uani 1 1 d . . . . .
C11 C 0.03396(11) 0.54541(9) 0.86020(12) 0.0211(3) Uani 1 1 d . . . . .
C8 C 0.10905(11) 0.60502(9) 0.85621(11) 0.0187(3) Uani 1 1 d . . . . .
C9 C 0.08822(11) 0.69305(9) 0.84421(11) 0.0179(3) Uani 1 1 d . . . . .
C4 C 0.16207(11) 0.74895(9) 0.84635(11) 0.0183(3) Uani 1 1 d . . . . .
C3 C 0.14050(11) 0.83728(9) 0.83676(11) 0.0196(3) Uani 1 1 d . . . . .
C12 C 0.21248(11) 0.89687(9) 0.84018(12) 0.0215(3) Uani 1 1 d . . . . .
C13 C 0.27635(11) 0.94384(9) 0.84577(11) 0.0209(3) Uani 1 1 d . . . . .
C14 C 0.35918(11) 0.99294(10) 0.85742(11) 0.0209(3) Uani 1 1 d . . . . .
C15 C 0.35735(12) 1.08104(10) 0.85366(12) 0.0244(4) Uani 1 1 d . . . . .
H15 H 0.2994 1.1105 0.8408 0.029 Uiso 1 1 calc R U . . .
C16 C 0.44089(13) 1.12516(10) 0.86879(13) 0.0285(4) Uani 1 1 d . . . . .
H16 H 0.4394 1.1850 0.8665 0.034 Uiso 1 1 calc R U . . .
C17 C 0.52668(12) 1.08349(11) 0.88730(12) 0.0280(4) Uani 1 1 d . . . . .
C20 C 0.61755(14) 1.13129(14) 0.90460(15) 0.0432(5) Uani 1 1 d . . . . .
H20A H 0.6708 1.1010 0.9525 0.065 Uiso 1 1 calc R U . . .
H20B H 0.6127 1.1877 0.9295 0.065 Uiso 1 1 calc R U . . .
H20C H 0.6283 1.1362 0.8430 0.065 Uiso 1 1 calc R U . . .
C1 C -0.01797(11) 0.80055(10) 0.81957(11) 0.0200(3) Uani 1 1 d . . . . .
C2 C 0.04961(11) 0.86244(10) 0.82414(11) 0.0213(3) Uani 1 1 d . . . . .
H2 H 0.0331 0.9205 0.8187 0.026 Uiso 1 1 calc R U . . .
C5 C 0.25267(11) 0.71643(10) 0.85706(12) 0.0217(3) Uani 1 1 d . . . . .
H5 H 0.3020 0.7539 0.8580 0.026 Uiso 1 1 calc R U . . .
C6 C 0.26966(11) 0.63182(10) 0.86608(12) 0.0233(3) Uani 1 1 d . . . . .
H6 H 0.3304 0.6106 0.8724 0.028 Uiso 1 1 calc R U . . .
C7 C 0.19714(11) 0.57559(10) 0.86609(12) 0.0217(3) Uani 1 1 d . . . . .
H7 H 0.2097 0.5168 0.8730 0.026 Uiso 1 1 calc R U . . .
C18 C 0.52731(12) 0.99595(11) 0.88980(12) 0.0271(4) Uani 1 1 d . . . . .
H18 H 0.5852 0.9666 0.9017 0.033 Uiso 1 1 calc R U . . .
C19 C 0.44531(12) 0.95096(10) 0.87527(12) 0.0236(3) Uani 1 1 d . . . . .
H19 H 0.4473 0.8911 0.8774 0.028 Uiso 1 1 calc R U . . .
C10 C -0.12023(12) 0.82632(10) 0.79508(13) 0.0245(4) Uani 1 1 d . . . . .
C40 C -0.12599(13) 0.90208(13) 0.05538(15) 0.0382(5) Uani 1 1 d . . . . .
H40A H -0.1122 0.9623 0.0533 0.057 Uiso 1 1 calc R U . . .
H40B H -0.1484 0.8914 0.1089 0.057 Uiso 1 1 calc R U . . .
H40C H -0.1752 0.8853 -0.0067 0.057 Uiso 1 1 calc R U . . .
C37 C -0.03670(12) 0.85146(11) 0.07166(12) 0.0259(4) Uani 1 1 d . . . . .
C38 C -0.03846(12) 0.76387(11) 0.07659(12) 0.0254(4) Uani 1 1 d . . . . .
H38 H -0.0959 0.7363 0.0712 0.031 Uiso 1 1 calc R U . . .
C39 C 0.04156(11) 0.71617(10) 0.08912(12) 0.0229(3) Uani 1 1 d . . . . .
H39 H 0.0384 0.6564 0.0919 0.028 Uiso 1 1 calc R U . . .
C34 C 0.12721(11) 0.75523(10) 0.09772(11) 0.0199(3) Uani 1 1 d . . . . .
C33 C 0.20914(11) 0.70396(9) 0.10994(11) 0.0211(3) Uani 1 1 d . . . . .
C32 C 0.27378(11) 0.65677(9) 0.11935(12) 0.0207(3) Uani 1 1 d . . . . .
C23 C 0.34731(11) 0.59699(9) 0.12751(11) 0.0193(3) Uani 1 1 d . . . . .
C24 C 0.32528(11) 0.50887(9) 0.11440(11) 0.0189(3) Uani 1 1 d . . . . .
C29 C 0.39949(11) 0.45226(9) 0.11876(11) 0.0183(3) Uani 1 1 d . . . . .
C28 C 0.37717(11) 0.36458(10) 0.10257(11) 0.0202(3) Uani 1 1 d . . . . .
C31 C 0.45200(12) 0.30273(10) 0.10163(12) 0.0240(4) Uani 1 1 d . . . . .
C36 C 0.04854(12) 0.89014(10) 0.08144(13) 0.0287(4) Uani 1 1 d . . . . .
H36 H 0.0514 0.9499 0.0792 0.034 Uiso 1 1 calc R U . . .
C35 C 0.12985(12) 0.84326(10) 0.09450(13) 0.0260(4) Uani 1 1 d . . . . .
H35 H 0.1875 0.8711 0.1013 0.031 Uiso 1 1 calc R U . . .
C22 C 0.44014(11) 0.62131(10) 0.14819(11) 0.0215(3) Uani 1 1 d . . . . .
H22 H 0.4579 0.6790 0.1583 0.026 Uiso 1 1 calc R U . . .
C21 C 0.50759(11) 0.55908(10) 0.15397(12) 0.0216(3) Uani 1 1 d . . . . .
C30 C 0.61113(12) 0.58235(10) 0.18105(13) 0.0264(4) Uani 1 1 d . . . . .
C25 C 0.23330(11) 0.47709(10) 0.09897(12) 0.0214(3) Uani 1 1 d . . . . .
H25 H 0.1838 0.5148 0.0969 0.026 Uiso 1 1 calc R U . . .
C26 C 0.21537(11) 0.39278(10) 0.08712(12) 0.0242(4) Uani 1 1 d . . . . .
H26 H 0.1540 0.3719 0.0786 0.029 Uiso 1 1 calc R U . . .
C27 C 0.28756(11) 0.33640(10) 0.08748(12) 0.0234(3) Uani 1 1 d . . . . .
H27 H 0.2737 0.2780 0.0771 0.028 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F4 C11 1.3412(18) . ?
F5 C11 1.3442(18) . ?
F6 C11 1.3489(17) . ?
F1 C10 1.3249(19) . ?
F3 C10 1.3405(19) . ?
F2 C10 1.325(2) . ?
F11 C31 1.3421(19) . ?
F10 C31 1.3429(19) . ?
F12 C31 1.3419(18) . ?
F8 C30 1.334(2) . ?
F7 C30 1.3344(19) . ?
F9 C30 1.333(2) . ?
N1 C1 1.3145(19) . ?
N1 C9 1.3643(19) . ?
N2 C21 1.318(2) . ?
N2 C29 1.361(2) . ?
C11 C8 1.495(2) . ?
C8 C7 1.368(2) . ?
C8 C9 1.428(2) . ?
C9 C4 1.417(2) . ?
C4 C5 1.418(2) . ?
C4 C3 1.433(2) . ?
C3 C2 1.377(2) . ?
C3 C12 1.428(2) . ?
C12 C13 1.198(2) . ?
C13 C14 1.431(2) . ?
C14 C15 1.398(2) . ?
C14 C19 1.399(2) . ?
C15 C16 1.389(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.391(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.388(2) . ?
C17 C20 1.507(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C1 C2 1.401(2) . ?
C1 C10 1.510(2) . ?
C2 H2 0.9500 . ?
C5 C6 1.363(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.413(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C18 C19 1.378(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C40 C37 1.513(2) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C37 C36 1.387(2) . ?
C37 C38 1.391(2) . ?
C38 C39 1.381(2) . ?
C38 H38 0.9500 . ?
C39 C34 1.399(2) . ?
C39 H39 0.9500 . ?
C34 C35 1.398(2) . ?
C34 C33 1.437(2) . ?
C33 C32 1.198(2) . ?
C32 C23 1.432(2) . ?
C23 C22 1.378(2) . ?
C23 C24 1.433(2) . ?
C24 C25 1.417(2) . ?
C24 C29 1.420(2) . ?
C29 C28 1.430(2) . ?
C28 C27 1.366(2) . ?
C28 C31 1.501(2) . ?
C36 C35 1.389(2) . ?
C36 H36 0.9500 . ?
C35 H35 0.9500 . ?
C22 C21 1.399(2) . ?
C22 H22 0.9500 . ?
C21 C30 1.513(2) . ?
C25 C26 1.363(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.409(2) . ?
C26 H26 0.9500 . ?
C27 H27 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 C9 116.49(13) . . ?
C21 N2 C29 116.46(13) . . ?
F4 C11 F5 106.40(12) . . ?
F4 C11 F6 105.91(12) . . ?
F5 C11 F6 105.93(12) . . ?
F4 C11 C8 113.67(13) . . ?
F5 C11 C8 112.39(13) . . ?
F6 C11 C8 111.97(13) . . ?
C7 C8 C9 120.59(14) . . ?
C7 C8 C11 120.28(14) . . ?
C9 C8 C11 119.12(13) . . ?
N1 C9 C4 123.35(13) . . ?
N1 C9 C8 118.46(13) . . ?
C4 C9 C8 118.18(14) . . ?
C9 C4 C5 119.78(14) . . ?
C9 C4 C3 117.37(14) . . ?
C5 C4 C3 122.84(14) . . ?
C2 C3 C12 121.55(14) . . ?
C2 C3 C4 118.45(14) . . ?
C12 C3 C4 120.00(14) . . ?
C13 C12 C3 176.57(17) . . ?
C12 C13 C14 174.04(17) . . ?
C15 C14 C19 119.11(15) . . ?
C15 C14 C13 122.36(15) . . ?
C19 C14 C13 118.52(14) . . ?
C16 C15 C14 119.56(16) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 121.37(16) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C18 C17 C16 118.48(16) . . ?
C18 C17 C20 120.08(17) . . ?
C16 C17 C20 121.44(17) . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N1 C1 C2 125.68(14) . . ?
N1 C1 C10 115.04(14) . . ?
C2 C1 C10 119.17(14) . . ?
C3 C2 C1 118.57(14) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C6 C5 C4 120.59(15) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 120.14(15) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 120.68(14) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C19 C18 C17 121.10(16) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C14 120.38(15) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
F1 C10 F2 107.53(14) . . ?
F1 C10 F3 106.28(13) . . ?
F2 C10 F3 105.97(14) . . ?
F1 C10 C1 113.39(13) . . ?
F2 C10 C1 111.33(13) . . ?
F3 C10 C1 111.91(14) . . ?
C37 C40 H40A 109.5 . . ?
C37 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C37 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C36 C37 C38 118.09(15) . . ?
C36 C37 C40 121.59(16) . . ?
C38 C37 C40 120.32(16) . . ?
C39 C38 C37 121.40(16) . . ?
C39 C38 H38 119.3 . . ?
C37 C38 H38 119.3 . . ?
C38 C39 C34 120.45(15) . . ?
C38 C39 H39 119.8 . . ?
C34 C39 H39 119.8 . . ?
C35 C34 C39 118.42(15) . . ?
C35 C34 C33 122.36(15) . . ?
C39 C34 C33 119.22(14) . . ?
C32 C33 C34 175.80(16) . . ?
C33 C32 C23 176.84(17) . . ?
C22 C23 C32 122.01(14) . . ?
C22 C23 C24 118.06(14) . . ?
C32 C23 C24 119.93(14) . . ?
C25 C24 C29 119.71(14) . . ?
C25 C24 C23 122.29(14) . . ?
C29 C24 C23 117.99(14) . . ?
N2 C29 C24 122.91(14) . . ?
N2 C29 C28 118.88(14) . . ?
C24 C29 C28 118.20(14) . . ?
C27 C28 C29 120.32(14) . . ?
C27 C28 C31 119.42(14) . . ?
C29 C28 C31 120.26(14) . . ?
F12 C31 F11 106.02(13) . . ?
F12 C31 F10 105.82(13) . . ?
F11 C31 F10 106.01(13) . . ?
F12 C31 C28 111.76(13) . . ?
F11 C31 C28 113.44(13) . . ?
F10 C31 C28 113.19(13) . . ?
C37 C36 C35 121.34(15) . . ?
C37 C36 H36 119.3 . . ?
C35 C36 H36 119.3 . . ?
C36 C35 C34 120.29(15) . . ?
C36 C35 H35 119.9 . . ?
C34 C35 H35 119.9 . . ?
C23 C22 C21 118.50(14) . . ?
C23 C22 H22 120.8 . . ?
C21 C22 H22 120.8 . . ?
N2 C21 C22 125.99(15) . . ?
N2 C21 C30 113.67(14) . . ?
C22 C21 C30 120.34(14) . . ?
F9 C30 F8 106.03(13) . . ?
F9 C30 F7 107.27(14) . . ?
F8 C30 F7 106.93(14) . . ?
F9 C30 C21 111.77(13) . . ?
F8 C30 C21 112.27(14) . . ?
F7 C30 C21 112.19(14) . . ?
C26 C25 C24 120.46(15) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C25 C26 C27 120.28(15) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C28 C27 C26 120.95(15) . . ?
C28 C27 H27 119.5 . . ?
C26 C27 H27 119.5 . . ?

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
F4 C11 C8 C7 -121.14(16) . . . . ?
F5 C11 C8 C7 117.93(16) . . . . ?
F6 C11 C8 C7 -1.2(2) . . . . ?
F4 C11 C8 C9 60.28(19) . . . . ?
F5 C11 C8 C9 -60.65(19) . . . . ?
F6 C11 C8 C9 -179.75(13) . . . . ?
C1 N1 C9 C4 -1.3(2) . . . . ?
C1 N1 C9 C8 179.71(14) . . . . ?
C7 C8 C9 N1 176.84(14) . . . . ?
C11 C8 C9 N1 -4.6(2) . . . . ?
C7 C8 C9 C4 -2.2(2) . . . . ?
C11 C8 C9 C4 176.37(14) . . . . ?
N1 C9 C4 C5 -177.02(14) . . . . ?
C8 C9 C4 C5 2.0(2) . . . . ?
N1 C9 C4 C3 2.6(2) . . . . ?
C8 C9 C4 C3 -178.40(14) . . . . ?
C9 C4 C3 C2 -1.3(2) . . . . ?
C5 C4 C3 C2 178.32(14) . . . . ?
C9 C4 C3 C12 178.84(14) . . . . ?
C5 C4 C3 C12 -1.5(2) . . . . ?
C19 C14 C15 C16 -0.8(2) . . . . ?
C13 C14 C15 C16 177.84(15) . . . . ?
C14 C15 C16 C17 0.3(3) . . . . ?
C15 C16 C17 C18 0.4(3) . . . . ?
C15 C16 C17 C20 -179.46(16) . . . . ?
C9 N1 C1 C2 -1.4(2) . . . . ?
C9 N1 C1 C10 174.91(13) . . . . ?
C12 C3 C2 C1 178.78(15) . . . . ?
C4 C3 C2 C1 -1.1(2) . . . . ?
N1 C1 C2 C3 2.6(2) . . . . ?
C10 C1 C2 C3 -173.54(14) . . . . ?
C9 C4 C5 C6 -0.5(2) . . . . ?
C3 C4 C5 C6 179.89(15) . . . . ?
C4 C5 C6 C7 -0.8(2) . . . . ?
C9 C8 C7 C6 0.9(2) . . . . ?
C11 C8 C7 C6 -177.62(15) . . . . ?
C5 C6 C7 C8 0.6(2) . . . . ?
C16 C17 C18 C19 -0.6(3) . . . . ?
C20 C17 C18 C19 179.27(16) . . . . ?
C17 C18 C19 C14 0.1(3) . . . . ?
C15 C14 C19 C18 0.6(2) . . . . ?
C13 C14 C19 C18 -178.08(15) . . . . ?
N1 C1 C10 F1 39.7(2) . . . . ?
C2 C1 C10 F1 -143.77(15) . . . . ?
N1 C1 C10 F2 -81.75(17) . . . . ?
C2 C1 C10 F2 94.82(18) . . . . ?
N1 C1 C10 F3 159.87(14) . . . . ?
C2 C1 C10 F3 -23.6(2) . . . . ?
C36 C37 C38 C39 -1.1(3) . . . . ?
C40 C37 C38 C39 178.48(16) . . . . ?
C37 C38 C39 C34 0.3(2) . . . . ?
C38 C39 C34 C35 0.8(2) . . . . ?
C38 C39 C34 C33 -179.52(15) . . . . ?
C22 C23 C24 C25 175.99(15) . . . . ?
C32 C23 C24 C25 -3.8(2) . . . . ?
C22 C23 C24 C29 -3.0(2) . . . . ?
C32 C23 C24 C29 177.21(14) . . . . ?
C21 N2 C29 C24 0.0(2) . . . . ?
C21 N2 C29 C28 -179.31(14) . . . . ?
C25 C24 C29 N2 -176.32(14) . . . . ?
C23 C24 C29 N2 2.7(2) . . . . ?
C25 C24 C29 C28 3.0(2) . . . . ?
C23 C24 C29 C28 -178.00(14) . . . . ?
N2 C29 C28 C27 176.61(15) . . . . ?
C24 C29 C28 C27 -2.7(2) . . . . ?
N2 C29 C28 C31 -3.6(2) . . . . ?
C24 C29 C28 C31 177.06(14) . . . . ?
C27 C28 C31 F12 3.0(2) . . . . ?
C29 C28 C31 F12 -176.75(14) . . . . ?
C27 C28 C31 F11 122.80(16) . . . . ?
C29 C28 C31 F11 -57.0(2) . . . . ?
C27 C28 C31 F10 -116.35(16) . . . . ?
C29 C28 C31 F10 63.89(19) . . . . ?
C38 C37 C36 C35 0.8(3) . . . . ?
C40 C37 C36 C35 -178.74(17) . . . . ?
C37 C36 C35 C34 0.2(3) . . . . ?
C39 C34 C35 C36 -1.0(2) . . . . ?
C33 C34 C35 C36 179.26(15) . . . . ?
C32 C23 C22 C21 -179.37(15) . . . . ?
C24 C23 C22 C21 0.9(2) . . . . ?
C29 N2 C21 C22 -2.5(2) . . . . ?
C29 N2 C21 C30 176.83(13) . . . . ?
C23 C22 C21 N2 2.1(3) . . . . ?
C23 C22 C21 C30 -177.19(14) . . . . ?
N2 C21 C30 F9 -55.03(19) . . . . ?
C22 C21 C30 F9 124.30(16) . . . . ?
N2 C21 C30 F8 63.98(18) . . . . ?
C22 C21 C30 F8 -116.69(16) . . . . ?
N2 C21 C30 F7 -175.56(14) . . . . ?
C22 C21 C30 F7 3.8(2) . . . . ?
C29 C24 C25 C26 -0.8(2) . . . . ?
C23 C24 C25 C26 -179.80(15) . . . . ?
C24 C25 C26 C27 -1.7(2) . . . . ?
C29 C28 C27 C26 0.3(2) . . . . ?
C31 C28 C27 C26 -179.51(15) . . . . ?
C25 C26 C27 C28 2.0(3) . . . . ?

_refine_diff_density_max         0.351
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.050

_shelxl_version_number           2014-3

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform'
####################################################################### 
# 
# 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_4E
_database_code_depnum_ccdc_archive 'CCDC 1585038'
_audit_update_record             
;
2017-11-10 deposited with the CCDC.
2018-03-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H8 F9 N'
_chemical_formula_sum            'C20 H8 F9 N'
_chemical_formula_weight         433.27

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.2613(2)
_cell_length_b                   15.7199(3)
_cell_length_c                   14.1251(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.8220(10)
_cell_angle_gamma                90
_cell_volume                     3384.59(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9963
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      28.46

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_F_000             1728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.170
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.958
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            75376
_diffrn_reflns_av_unetI/netI     0.0118
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.336
_diffrn_reflns_theta_max         28.522
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8511
_reflns_number_gt                7198
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT-plus (Bruker, 2008)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2008)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 2012)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0443P)²+2.3720P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8511
_refine_ls_number_parameters     541
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.1019
_refine_ls_wR_factor_gt          0.0918
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F6 F 0.47850(6) 1.29652(5) 0.36040(7) 0.0301(2) Uani 1 1 d . . . . .
F5 F 0.56168(6) 1.20417(6) 0.43215(7) 0.0303(2) Uani 1 1 d . . . . .
F4 F 0.54760(6) 1.20487(6) 0.27993(7) 0.02778(19) Uani 1 1 d . . . . .
F1 F 0.63376(7) 0.83910(7) 0.34061(11) 0.0558(4) Uani 1 1 d . . . . .
F3 F 0.65251(7) 0.94832(8) 0.25587(8) 0.0501(3) Uani 1 1 d . . . . .
F2 F 0.68295(6) 0.95456(8) 0.40339(9) 0.0482(3) Uani 1 1 d . . . . .
F7 F 0.33302(5) 0.65789(6) 0.48353(6) 0.02363(18) Uani 1 1 d . . . . .
F8 F 0.28193(5) 0.54582(5) 0.41287(7) 0.02641(19) Uani 1 1 d . . . . .
F9 F 0.32438(5) 0.65207(6) 0.33123(6) 0.02691(19) Uani 1 1 d . . . . .
F16 F 0.16653(5) 1.09398(6) 0.01970(7) 0.02774(19) Uani 1 1 d . . . . .
F13 F -0.06857(5) 0.59423(6) 0.05934(6) 0.02593(18) Uani 1 1 d . . . . .
F14 F -0.05885(5) 0.57172(5) 0.21002(6) 0.02535(18) Uani 1 1 d . . . . .
F15 F 0.00818(6) 0.48933(5) 0.11590(7) 0.02779(19) Uani 1 1 d . . . . .
F18 F 0.17577(6) 1.14086(6) 0.16278(6) 0.0299(2) Uani 1 1 d . . . . .
F17 F 0.21667(6) 1.21964(6) 0.04878(7) 0.0306(2) Uani 1 1 d . . . . .
F10 F -0.13370(6) 0.94169(5) 0.19739(7) 0.02835(19) Uani 1 1 d . . . . .
F11 F -0.13519(6) 0.84455(6) 0.30352(7) 0.0339(2) Uani 1 1 d . . . . .
F12 F -0.18706(6) 0.81870(6) 0.16255(8) 0.0339(2) Uani 1 1 d . . . . .
N1 N 0.52311(7) 1.03511(7) 0.35685(8) 0.0188(2) Uani 1 1 d . . . . .
N2 N -0.02530(7) 0.74622(7) 0.17156(8) 0.0176(2) Uani 1 1 d . . . . .
C11 C 0.50356(9) 1.21431(9) 0.35880(10) 0.0211(3) Uani 1 1 d . . . . .
C8 C 0.42635(8) 1.15527(8) 0.36354(9) 0.0188(2) Uani 1 1 d . . . . .
C9 C 0.44011(8) 1.06543(8) 0.36471(9) 0.0182(2) Uani 1 1 d . . . . .
C4 C 0.36600(8) 1.01122(8) 0.37183(9) 0.0184(2) Uani 1 1 d . . . . .
C3 C 0.38111(9) 0.92161(9) 0.37290(9) 0.0197(3) Uani 1 1 d . . . . .
C12 C 0.30979(9) 0.86343(9) 0.38230(10) 0.0214(3) Uani 1 1 d . . . . .
C13 C 0.25100(9) 0.81418(9) 0.39099(10) 0.0204(3) Uani 1 1 d . . . . .
C14 C 0.17916(8) 0.75659(8) 0.40205(9) 0.0174(2) Uani 1 1 d . . . . .
C15 C 0.19151(8) 0.66798(8) 0.40965(9) 0.0163(2) Uani 1 1 d . . . . .
C16 C 0.12058(8) 0.61450(9) 0.42089(10) 0.0193(3) Uani 1 1 d . . . . .
H16 H 0.1294 0.5548 0.4259 0.023 Uiso 1 1 calc R U . . .
C17 C 0.03647(9) 0.64811(10) 0.42484(10) 0.0227(3) Uani 1 1 d . . . . .
H17 H -0.0121 0.6113 0.4320 0.027 Uiso 1 1 calc R U . . .
C1 C 0.53277(9) 0.95191(9) 0.35474(10) 0.0202(3) Uani 1 1 d . . . . .
C10 C 0.62577(9) 0.92300(9) 0.33917(11) 0.0237(3) Uani 1 1 d . . . . .
C2 C 0.46550(9) 0.89194(9) 0.36336(10) 0.0215(3) Uani 1 1 d . . . . .
H2 H 0.4776 0.8327 0.3627 0.026 Uiso 1 1 calc R U . . .
C5 C 0.28112(9) 1.04727(9) 0.37608(10) 0.0215(3) Uani 1 1 d . . . . .
H5 H 0.2316 1.0112 0.3813 0.026 Uiso 1 1 calc R U . . .
C6 C 0.26992(9) 1.13326(9) 0.37277(10) 0.0230(3) Uani 1 1 d . . . . .
H6 H 0.2126 1.1567 0.3746 0.028 Uiso 1 1 calc R U . . .
C7 C 0.34327(9) 1.18780(9) 0.36666(10) 0.0218(3) Uani 1 1 d . . . . .
H7 H 0.3348 1.2477 0.3647 0.026 Uiso 1 1 calc R U . . .
C20 C 0.28217(8) 0.63091(8) 0.40869(9) 0.0184(2) Uani 1 1 d . . . . .
C18 C 0.02356(9) 0.73513(10) 0.41834(10) 0.0230(3) Uani 1 1 d . . . . .
H18 H -0.0339 0.7579 0.4216 0.028 Uiso 1 1 calc R U . . .
C19 C 0.09411(9) 0.78924(9) 0.40710(9) 0.0204(3) Uani 1 1 d . . . . .
H19 H 0.0847 0.8489 0.4028 0.024 Uiso 1 1 calc R U . . .
C40 C 0.21756(9) 1.13976(9) 0.08174(10) 0.0213(3) Uani 1 1 d . . . . .
C35 C 0.30856(8) 1.10384(8) 0.09341(9) 0.0180(2) Uani 1 1 d . . . . .
C34 C 0.32133(8) 1.01952(8) 0.12438(9) 0.0178(2) Uani 1 1 d . . . . .
C33 C 0.24947(9) 0.96452(9) 0.14425(10) 0.0197(3) Uani 1 1 d . . . . .
C32 C 0.19090(9) 0.91609(9) 0.15774(10) 0.0205(3) Uani 1 1 d . . . . .
C23 C 0.11929(9) 0.85827(8) 0.16637(9) 0.0184(2) Uani 1 1 d . . . . .
C24 C 0.13202(8) 0.76882(8) 0.15549(9) 0.0176(2) Uani 1 1 d . . . . .
C29 C 0.05657(8) 0.71602(8) 0.15579(9) 0.0170(2) Uani 1 1 d . . . . .
C28 C 0.06703(9) 0.62707(8) 0.13902(9) 0.0183(2) Uani 1 1 d . . . . .
C31 C -0.01285(9) 0.57131(8) 0.13160(10) 0.0206(3) Uani 1 1 d . . . . .
C21 C -0.03241(8) 0.82862(8) 0.18558(9) 0.0179(2) Uani 1 1 d . . . . .
C22 C 0.03605(9) 0.88797(8) 0.18178(9) 0.0198(3) Uani 1 1 d . . . . .
H22 H 0.0254 0.9470 0.1896 0.024 Uiso 1 1 calc R U . . .
C25 C 0.21559(9) 0.73208(9) 0.14309(9) 0.0201(3) Uani 1 1 d . . . . .
H25 H 0.2662 0.7673 0.1435 0.024 Uiso 1 1 calc R U . . .
C26 C 0.22383(9) 0.64622(9) 0.13050(10) 0.0218(3) Uani 1 1 d . . . . .
H26 H 0.2802 0.6220 0.1240 0.026 Uiso 1 1 calc R U . . .
C27 C 0.14872(9) 0.59344(9) 0.12707(10) 0.0207(3) Uani 1 1 d . . . . .
H27 H 0.1549 0.5341 0.1164 0.025 Uiso 1 1 calc R U . . .
C36 C 0.37976(9) 1.15388(9) 0.07225(10) 0.0227(3) Uani 1 1 d . . . . .
H36 H 0.3707 1.2107 0.0512 0.027 Uiso 1 1 calc R U . . .
C37 C 0.46426(9) 1.12118(10) 0.08172(11) 0.0260(3) Uani 1 1 d . . . . .
H37 H 0.5129 1.1557 0.0673 0.031 Uiso 1 1 calc R U . . .
C38 C 0.47766(9) 1.03823(10) 0.11217(10) 0.0251(3) Uani 1 1 d . . . . .
H38 H 0.5356 1.0162 0.1191 0.030 Uiso 1 1 calc R U . . .
C39 C 0.40710(9) 0.98744(9) 0.13255(10) 0.0216(3) Uani 1 1 d . . . . .
H39 H 0.4168 0.9303 0.1523 0.026 Uiso 1 1 calc R U . . .
C30 C -0.12278(9) 0.85807(8) 0.21178(10) 0.0205(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
F6 C11 1.3483(16) . ?
F5 C11 1.3398(17) . ?
F4 C11 1.3374(16) . ?
F1 C10 1.3246(17) . ?
F3 C10 1.3254(18) . ?
F2 C10 1.3238(18) . ?
F7 C20 1.3487(15) . ?
F8 C20 1.3389(15) . ?
F9 C20 1.3387(15) . ?
F16 C40 1.3510(16) . ?
F13 C31 1.3451(16) . ?
F14 C31 1.3402(16) . ?
F15 C31 1.3491(15) . ?
F18 C40 1.3375(16) . ?
F17 C40 1.3391(16) . ?
F10 C30 1.3392(15) . ?
F11 C30 1.3358(17) . ?
F12 C30 1.3274(16) . ?
N1 C1 1.3166(17) . ?
N1 C9 1.3631(17) . ?
N2 C21 1.3157(17) . ?
N2 C29 1.3652(16) . ?
C11 C8 1.5040(18) . ?
C8 C7 1.3698(19) . ?
C8 C9 1.4278(18) . ?
C9 C4 1.4237(18) . ?
C4 C5 1.4179(18) . ?
C4 C3 1.4273(18) . ?
C3 C2 1.3826(19) . ?
C3 C12 1.4330(18) . ?
C12 C13 1.196(2) . ?
C13 C14 1.4362(18) . ?
C14 C19 1.4009(18) . ?
C14 C15 1.4091(18) . ?
C15 C16 1.3860(18) . ?
C15 C20 1.5019(17) . ?
C16 C17 1.3918(18) . ?
C16 H16 0.9500 . ?
C17 C18 1.384(2) . ?
C17 H17 0.9500 . ?
C1 C2 1.4035(19) . ?
C1 C10 1.5167(19) . ?
C2 H2 0.9500 . ?
C5 C6 1.363(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.4162(19) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C18 C19 1.387(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C40 C35 1.5007(18) . ?
C35 C36 1.3860(18) . ?
C35 C34 1.4063(18) . ?
C34 C39 1.4022(18) . ?
C34 C33 1.4350(18) . ?
C33 C32 1.197(2) . ?
C32 C23 1.4312(18) . ?
C23 C22 1.3807(19) . ?
C23 C24 1.4289(18) . ?
C24 C25 1.4188(18) . ?
C24 C29 1.4195(18) . ?
C29 C28 1.4284(18) . ?
C28 C27 1.3723(18) . ?
C28 C31 1.5011(18) . ?
C21 C22 1.4036(18) . ?
C21 C30 1.5178(18) . ?
C22 H22 0.9500 . ?
C25 C26 1.368(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.4138(19) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C36 C37 1.388(2) . ?
C36 H36 0.9500 . ?
C37 C38 1.385(2) . ?
C37 H37 0.9500 . ?
C38 C39 1.382(2) . ?
C38 H38 0.9500 . ?
C39 H39 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 C9 117.04(12) . . ?
C21 N2 C29 116.73(11) . . ?
F4 C11 F5 106.87(11) . . ?
F4 C11 F6 105.95(11) . . ?
F5 C11 F6 106.18(11) . . ?
F4 C11 C8 113.30(11) . . ?
F5 C11 C8 112.49(11) . . ?
F6 C11 C8 111.54(11) . . ?
C7 C8 C9 120.32(12) . . ?
C7 C8 C11 119.97(12) . . ?
C9 C8 C11 119.72(12) . . ?
N1 C9 C4 122.77(12) . . ?
N1 C9 C8 118.79(12) . . ?
C4 C9 C8 118.42(12) . . ?
C5 C4 C9 119.63(12) . . ?
C5 C4 C3 122.79(12) . . ?
C9 C4 C3 117.57(12) . . ?
C2 C3 C4 118.87(12) . . ?
C2 C3 C12 120.61(13) . . ?
C4 C3 C12 120.52(12) . . ?
C13 C12 C3 179.08(16) . . ?
C12 C13 C14 178.71(15) . . ?
C19 C14 C15 118.62(12) . . ?
C19 C14 C13 119.26(12) . . ?
C15 C14 C13 122.11(12) . . ?
C16 C15 C14 120.41(12) . . ?
C16 C15 C20 119.38(12) . . ?
C14 C15 C20 120.18(11) . . ?
C15 C16 C17 120.09(13) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 120.07(12) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
N1 C1 C2 125.60(13) . . ?
N1 C1 C10 114.05(12) . . ?
C2 C1 C10 120.33(12) . . ?
F2 C10 F1 107.79(13) . . ?
F2 C10 F3 105.93(13) . . ?
F1 C10 F3 106.29(14) . . ?
F2 C10 C1 112.23(12) . . ?
F1 C10 C1 112.47(12) . . ?
F3 C10 C1 111.71(12) . . ?
C3 C2 C1 118.08(13) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C6 C5 C4 120.55(12) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 120.29(13) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 120.77(13) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
F9 C20 F8 106.66(11) . . ?
F9 C20 F7 106.32(10) . . ?
F8 C20 F7 106.39(10) . . ?
F9 C20 C15 113.05(11) . . ?
F8 C20 C15 112.50(11) . . ?
F7 C20 C15 111.45(11) . . ?
C17 C18 C19 120.31(12) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C14 120.50(13) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.7 . . ?
F18 C40 F17 106.76(11) . . ?
F18 C40 F16 106.15(11) . . ?
F17 C40 F16 106.16(11) . . ?
F18 C40 C35 112.86(11) . . ?
F17 C40 C35 112.61(11) . . ?
F16 C40 C35 111.81(11) . . ?
C36 C35 C34 120.25(12) . . ?
C36 C35 C40 119.60(12) . . ?
C34 C35 C40 120.14(11) . . ?
C39 C34 C35 118.63(12) . . ?
C39 C34 C33 119.11(12) . . ?
C35 C34 C33 122.22(12) . . ?
C32 C33 C34 176.97(15) . . ?
C33 C32 C23 175.69(14) . . ?
C22 C23 C24 118.73(12) . . ?
C22 C23 C32 120.74(12) . . ?
C24 C23 C32 120.49(12) . . ?
C25 C24 C29 119.77(12) . . ?
C25 C24 C23 122.80(12) . . ?
C29 C24 C23 117.42(12) . . ?
N2 C29 C24 123.11(12) . . ?
N2 C29 C28 118.56(11) . . ?
C24 C29 C28 118.33(12) . . ?
C27 C28 C29 120.47(12) . . ?
C27 C28 C31 120.40(12) . . ?
C29 C28 C31 119.10(11) . . ?
F14 C31 F13 106.78(11) . . ?
F14 C31 F15 106.20(11) . . ?
F13 C31 F15 106.12(11) . . ?
F14 C31 C28 113.34(11) . . ?
F13 C31 C28 112.18(11) . . ?
F15 C31 C28 111.74(11) . . ?
N2 C21 C22 125.56(12) . . ?
N2 C21 C30 114.81(11) . . ?
C22 C21 C30 119.58(12) . . ?
C23 C22 C21 118.27(12) . . ?
C23 C22 H22 120.9 . . ?
C21 C22 H22 120.9 . . ?
C26 C25 C24 120.44(12) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C25 C26 C27 120.26(12) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C28 C27 C26 120.64(13) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C35 C36 C37 120.23(13) . . ?
C35 C36 H36 119.9 . . ?
C37 C36 H36 119.9 . . ?
C38 C37 C36 120.04(13) . . ?
C38 C37 H37 120.0 . . ?
C36 C37 H37 120.0 . . ?
C39 C38 C37 120.25(13) . . ?
C39 C38 H38 119.9 . . ?
C37 C38 H38 119.9 . . ?
C38 C39 C34 120.59(13) . . ?
C38 C39 H39 119.7 . . ?
C34 C39 H39 119.7 . . ?
F12 C30 F11 107.31(11) . . ?
F12 C30 F10 107.15(11) . . ?
F11 C30 F10 106.32(11) . . ?
F12 C30 C21 112.77(11) . . ?
F11 C30 C21 111.22(11) . . ?
F10 C30 C21 111.73(11) . . ?

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
F4 C11 C8 C7 -118.07(14) . . . . ?
F5 C11 C8 C7 120.57(14) . . . . ?
F6 C11 C8 C7 1.38(18) . . . . ?
F4 C11 C8 C9 61.89(17) . . . . ?
F5 C11 C8 C9 -59.47(17) . . . . ?
F6 C11 C8 C9 -178.66(12) . . . . ?
C1 N1 C9 C4 0.88(19) . . . . ?
C1 N1 C9 C8 -177.60(12) . . . . ?
C7 C8 C9 N1 176.82(12) . . . . ?
C11 C8 C9 N1 -3.14(19) . . . . ?
C7 C8 C9 C4 -1.7(2) . . . . ?
C11 C8 C9 C4 178.32(12) . . . . ?
N1 C9 C4 C5 -177.53(12) . . . . ?
C8 C9 C4 C5 0.95(19) . . . . ?
N1 C9 C4 C3 1.53(19) . . . . ?
C8 C9 C4 C3 -179.99(12) . . . . ?
C5 C4 C3 C2 176.56(13) . . . . ?
C9 C4 C3 C2 -2.47(19) . . . . ?
C5 C4 C3 C12 -2.5(2) . . . . ?
C9 C4 C3 C12 178.44(12) . . . . ?
C19 C14 C15 C16 0.67(19) . . . . ?
C13 C14 C15 C16 179.57(12) . . . . ?
C19 C14 C15 C20 -177.42(12) . . . . ?
C13 C14 C15 C20 1.49(19) . . . . ?
C14 C15 C16 C17 -0.1(2) . . . . ?
C20 C15 C16 C17 178.03(12) . . . . ?
C15 C16 C17 C18 -0.5(2) . . . . ?
C9 N1 C1 C2 -2.5(2) . . . . ?
C9 N1 C1 C10 176.04(11) . . . . ?
N1 C1 C10 F2 56.12(17) . . . . ?
C2 C1 C10 F2 -125.29(15) . . . . ?
N1 C1 C10 F1 177.88(13) . . . . ?
C2 C1 C10 F1 -3.5(2) . . . . ?
N1 C1 C10 F3 -62.69(17) . . . . ?
C2 C1 C10 F3 115.90(15) . . . . ?
C4 C3 C2 C1 1.1(2) . . . . ?
C12 C3 C2 C1 -179.79(12) . . . . ?
N1 C1 C2 C3 1.5(2) . . . . ?
C10 C1 C2 C3 -176.94(13) . . . . ?
C9 C4 C5 C6 0.4(2) . . . . ?
C3 C4 C5 C6 -178.57(13) . . . . ?
C4 C5 C6 C7 -1.1(2) . . . . ?
C9 C8 C7 C6 1.1(2) . . . . ?
C11 C8 C7 C6 -178.91(13) . . . . ?
C5 C6 C7 C8 0.3(2) . . . . ?
C16 C15 C20 F9 125.21(13) . . . . ?
C14 C15 C20 F9 -56.69(16) . . . . ?
C16 C15 C20 F8 4.30(17) . . . . ?
C14 C15 C20 F8 -177.59(11) . . . . ?
C16 C15 C20 F7 -115.10(13) . . . . ?
C14 C15 C20 F7 63.00(16) . . . . ?
C16 C17 C18 C19 0.5(2) . . . . ?
C17 C18 C19 C14 0.1(2) . . . . ?
C15 C14 C19 C18 -0.68(19) . . . . ?
C13 C14 C19 C18 -179.61(12) . . . . ?
F18 C40 C35 C36 -119.72(14) . . . . ?
F17 C40 C35 C36 1.26(18) . . . . ?
F16 C40 C35 C36 120.69(14) . . . . ?
F18 C40 C35 C34 61.14(16) . . . . ?
F17 C40 C35 C34 -177.88(12) . . . . ?
F16 C40 C35 C34 -58.45(17) . . . . ?
C36 C35 C34 C39 -0.48(19) . . . . ?
C40 C35 C34 C39 178.65(12) . . . . ?
C36 C35 C34 C33 -178.01(13) . . . . ?
C40 C35 C34 C33 1.13(19) . . . . ?
C22 C23 C24 C25 -177.50(12) . . . . ?
C32 C23 C24 C25 4.9(2) . . . . ?
C22 C23 C24 C29 3.56(18) . . . . ?
C32 C23 C24 C29 -174.04(12) . . . . ?
C21 N2 C29 C24 0.96(18) . . . . ?
C21 N2 C29 C28 -179.20(12) . . . . ?
C25 C24 C29 N2 176.96(12) . . . . ?
C23 C24 C29 N2 -4.06(19) . . . . ?
C25 C24 C29 C28 -2.88(18) . . . . ?
C23 C24 C29 C28 176.10(12) . . . . ?
N2 C29 C28 C27 -177.07(12) . . . . ?
C24 C29 C28 C27 2.78(19) . . . . ?
N2 C29 C28 C31 4.83(18) . . . . ?
C24 C29 C28 C31 -175.33(12) . . . . ?
C27 C28 C31 F14 121.94(13) . . . . ?
C29 C28 C31 F14 -59.95(16) . . . . ?
C27 C28 C31 F13 -117.04(14) . . . . ?
C29 C28 C31 F13 61.06(16) . . . . ?
C27 C28 C31 F15 2.00(18) . . . . ?
C29 C28 C31 F15 -179.90(11) . . . . ?
C29 N2 C21 C22 2.79(19) . . . . ?
C29 N2 C21 C30 -174.60(11) . . . . ?
C24 C23 C22 C21 -0.29(19) . . . . ?
C32 C23 C22 C21 177.30(12) . . . . ?
N2 C21 C22 C23 -3.1(2) . . . . ?
C30 C21 C22 C23 174.13(12) . . . . ?
C29 C24 C25 C26 0.64(19) . . . . ?
C23 C24 C25 C26 -178.28(13) . . . . ?
C24 C25 C26 C27 1.8(2) . . . . ?
C29 C28 C27 C26 -0.4(2) . . . . ?
C31 C28 C27 C26 177.65(12) . . . . ?
C25 C26 C27 C28 -1.9(2) . . . . ?
C34 C35 C36 C37 -0.2(2) . . . . ?
C40 C35 C36 C37 -179.30(13) . . . . ?
C35 C36 C37 C38 0.2(2) . . . . ?
C36 C37 C38 C39 0.5(2) . . . . ?
C37 C38 C39 C34 -1.2(2) . . . . ?
C35 C34 C39 C38 1.1(2) . . . . ?
C33 C34 C39 C38 178.75(13) . . . . ?
N2 C21 C30 F12 -40.54(16) . . . . ?
C22 C21 C30 F12 141.90(13) . . . . ?
N2 C21 C30 F11 80.07(15) . . . . ?
C22 C21 C30 F11 -97.49(14) . . . . ?
N2 C21 C30 F10 -161.30(12) . . . . ?
C22 C21 C30 F10 21.14(17) . . . . ?

_refine_diff_density_max         0.532
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.053

_shelxl_version_number           2014-3

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform'
####################################################################### 
# 
# 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_4P
_database_code_depnum_ccdc_archive 'CCDC 1585044'
_audit_update_record             
;
2017-11-10 deposited with the CCDC.
2018-03-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H12 F3 N'
_chemical_formula_sum            'C19 H12 F3 N'
_chemical_formula_weight         311.30

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.5779(2)
_cell_length_b                   8.9018(2)
_cell_length_c                   16.0143(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.6110(10)
_cell_angle_gamma                90
_cell_volume                     1490.95(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9888
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      28.75

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.431
_exptl_crystal_size_mid          0.278
_exptl_crystal_size_min          0.262
_exptl_absorpt_coefficient_mu    0.107
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.946
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18792
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.625
_diffrn_reflns_theta_max         28.752
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3783
_reflns_number_gt                3103
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT-plus (Bruker, 2008)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2008)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 2012)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0704P)²+0.6222P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3783
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1332
_refine_ls_wR_factor_gt          0.1234
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C19 C 0.98586(16) 0.84223(17) 0.16962(12) 0.0368(4) Uani 1 1 d . . . . .
H19A H 1.0672 0.8445 0.1473 0.055 Uiso 1 1 calc R U . . .
H19B H 0.9284 0.9189 0.1411 0.055 Uiso 1 1 calc R U . . .
H19C H 1.0014 0.8627 0.2304 0.055 Uiso 1 1 calc R U . . .
C16 C 0.92529(14) 0.68926(15) 0.15427(10) 0.0266(3) Uani 1 1 d . . . . .
C15 C 0.80869(14) 0.65717(15) 0.18018(9) 0.0247(3) Uani 1 1 d . . . . .
H15 H 0.7667 0.7328 0.2077 0.030 Uiso 1 1 calc R U . . .
C14 C 0.75244(13) 0.51683(15) 0.16669(9) 0.0242(3) Uani 1 1 d . . . . .
H14 H 0.6727 0.4971 0.1851 0.029 Uiso 1 1 calc R U . . .
C13 C 0.81264(13) 0.40432(14) 0.12613(9) 0.0234(3) Uani 1 1 d . . . . .
C12 C 0.75434(13) 0.25924(15) 0.11134(9) 0.0247(3) Uani 1 1 d . . . . .
C11 C 0.70357(13) 0.13921(15) 0.09997(9) 0.0239(3) Uani 1 1 d . . . . .
C3 C 0.64057(12) -0.00295(14) 0.08653(8) 0.0217(3) Uani 1 1 d . . . . .
C2 C 0.54905(13) -0.04536(15) 0.13485(9) 0.0228(3) Uani 1 1 d . . . . .
H2 H 0.5264 0.0186 0.1777 0.027 Uiso 1 1 calc R U . . .
C1 C 0.49033(12) -0.18635(14) 0.11862(9) 0.0219(3) Uani 1 1 d . . . . .
C10 C 0.39337(14) -0.24092(15) 0.17166(10) 0.0271(3) Uani 1 1 d . . . . .
C9 C 0.60401(12) -0.24228(14) 0.01203(8) 0.0218(3) Uani 1 1 d . . . . .
C4 C 0.67068(12) -0.10277(14) 0.02252(8) 0.0213(3) Uani 1 1 d . . . . .
C5 C 0.76223(13) -0.06919(16) -0.03071(9) 0.0263(3) Uani 1 1 d . . . . .
H5 H 0.8076 0.0232 -0.0242 0.032 Uiso 1 1 calc R U . . .
C6 C 0.78570(15) -0.16905(17) -0.09143(10) 0.0311(3) Uani 1 1 d . . . . .
H6 H 0.8466 -0.1450 -0.1274 0.037 Uiso 1 1 calc R U . . .
C7 C 0.71987(16) -0.30822(17) -0.10122(10) 0.0314(3) Uani 1 1 d . . . . .
H7 H 0.7376 -0.3770 -0.1433 0.038 Uiso 1 1 calc R U . . .
C8 C 0.63125(14) -0.34420(16) -0.05070(9) 0.0269(3) Uani 1 1 d . . . . .
H8 H 0.5878 -0.4378 -0.0577 0.032 Uiso 1 1 calc R U . . .
C17 C 0.98516(14) 0.57651(17) 0.11400(11) 0.0323(3) Uani 1 1 d . . . . .
H17 H 1.0651 0.5965 0.0960 0.039 Uiso 1 1 calc R U . . .
C18 C 0.92996(14) 0.43555(16) 0.09983(10) 0.0307(3) Uani 1 1 d . . . . .
H18 H 0.9720 0.3602 0.0722 0.037 Uiso 1 1 calc R U . . .
N1 N 0.51448(11) -0.28263(12) 0.06097(7) 0.0221(2) Uani 1 1 d . . . . .
F1 F 0.44158(11) -0.34871(12) 0.22514(8) 0.0523(3) Uani 1 1 d . . . . .
F2 F 0.35169(9) -0.13218(10) 0.21829(6) 0.0361(2) Uani 1 1 d . . . . .
F3 F 0.28973(9) -0.29857(13) 0.12473(7) 0.0468(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
C19 C16 1.5094(19) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C16 C15 1.389(2) . ?
C16 C17 1.395(2) . ?
C15 C14 1.3867(18) . ?
C15 H15 0.9500 . ?
C14 C13 1.3981(19) . ?
C14 H14 0.9500 . ?
C13 C18 1.397(2) . ?
C13 C12 1.4355(18) . ?
C12 C11 1.1975(19) . ?
C11 C3 1.4314(17) . ?
C3 C2 1.3795(19) . ?
C3 C4 1.4282(18) . ?
C2 C1 1.4071(17) . ?
C2 H2 0.9500 . ?
C1 N1 1.3126(18) . ?
C1 C10 1.5067(19) . ?
C10 F3 1.3354(18) . ?
C10 F1 1.3355(18) . ?
C10 F2 1.3371(17) . ?
C9 N1 1.3647(18) . ?
C9 C8 1.4150(19) . ?
C9 C4 1.4256(17) . ?
C4 C5 1.4144(19) . ?
C5 C6 1.367(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.418(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.365(2) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C17 C18 1.3884(19) . ?
C17 H17 0.9500 . ?
C18 H18 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
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C15 C16 C17 118.37(12) . . ?
C15 C16 C19 120.74(13) . . ?
C17 C16 C19 120.88(14) . . ?
C14 C15 C16 121.22(13) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C14 C13 120.21(13) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C18 C13 C14 118.98(12) . . ?
C18 C13 C12 120.56(13) . . ?
C14 C13 C12 120.45(12) . . ?
C11 C12 C13 178.54(16) . . ?
C12 C11 C3 178.90(15) . . ?
C2 C3 C4 118.88(12) . . ?
C2 C3 C11 120.51(12) . . ?
C4 C3 C11 120.61(12) . . ?
C3 C2 C1 117.90(12) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
N1 C1 C2 125.82(13) . . ?
N1 C1 C10 113.99(11) . . ?
C2 C1 C10 120.16(12) . . ?
F3 C10 F1 106.70(12) . . ?
F3 C10 F2 106.32(12) . . ?
F1 C10 F2 106.74(13) . . ?
F3 C10 C1 112.18(12) . . ?
F1 C10 C1 111.49(12) . . ?
F2 C10 C1 112.99(11) . . ?
N1 C9 C8 118.13(12) . . ?
N1 C9 C4 122.36(12) . . ?
C8 C9 C4 119.50(12) . . ?
C5 C4 C9 118.97(12) . . ?
C5 C4 C3 123.19(12) . . ?
C9 C4 C3 117.84(12) . . ?
C6 C5 C4 120.32(13) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 120.53(13) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C8 C7 C6 120.59(14) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 120.09(13) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C18 C17 C16 121.12(14) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C13 120.10(13) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?
C1 N1 C9 117.19(11) . . ?

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
C17 C16 C15 C14 0.0(2) . . . . ?
C19 C16 C15 C14 -179.74(14) . . . . ?
C16 C15 C14 C13 -0.2(2) . . . . ?
C15 C14 C13 C18 0.2(2) . . . . ?
C15 C14 C13 C12 -179.46(13) . . . . ?
C4 C3 C2 C1 0.38(19) . . . . ?
C11 C3 C2 C1 179.92(12) . . . . ?
C3 C2 C1 N1 -0.2(2) . . . . ?
C3 C2 C1 C10 177.67(12) . . . . ?
N1 C1 C10 F3 -47.60(17) . . . . ?
C2 C1 C10 F3 134.33(13) . . . . ?
N1 C1 C10 F1 71.99(16) . . . . ?
C2 C1 C10 F1 -106.07(15) . . . . ?
N1 C1 C10 F2 -167.78(12) . . . . ?
C2 C1 C10 F2 14.15(19) . . . . ?
N1 C9 C4 C5 179.96(12) . . . . ?
C8 C9 C4 C5 0.41(19) . . . . ?
N1 C9 C4 C3 -0.42(19) . . . . ?
C8 C9 C4 C3 -179.96(12) . . . . ?
C2 C3 C4 C5 179.49(13) . . . . ?
C11 C3 C4 C5 0.0(2) . . . . ?
C2 C3 C4 C9 -0.11(18) . . . . ?
C11 C3 C4 C9 -179.65(12) . . . . ?
C9 C4 C5 C6 0.3(2) . . . . ?
C3 C4 C5 C6 -179.32(13) . . . . ?
C4 C5 C6 C7 -0.8(2) . . . . ?
C5 C6 C7 C8 0.6(2) . . . . ?
C6 C7 C8 C9 0.1(2) . . . . ?
N1 C9 C8 C7 179.82(13) . . . . ?
C4 C9 C8 C7 -0.6(2) . . . . ?
C15 C16 C17 C18 0.1(2) . . . . ?
C19 C16 C17 C18 179.90(15) . . . . ?
C16 C17 C18 C13 -0.1(2) . . . . ?
C14 C13 C18 C17 0.0(2) . . . . ?
C12 C13 C18 C17 179.62(14) . . . . ?
C2 C1 N1 C9 -0.4(2) . . . . ?
C10 C1 N1 C9 -178.30(11) . . . . ?
C8 C9 N1 C1 -179.81(12) . . . . ?
C4 C9 N1 C1 0.65(19) . . . . ?

_refine_diff_density_max         0.490
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.053

_shelxl_version_number           2014-3

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform'
####################################################################### 
# 
# 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_4I
_database_code_depnum_ccdc_archive 'CCDC 1585039'
_audit_update_record             
;
2017-11-10 deposited with the CCDC.
2018-03-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H9 F6 N'
_chemical_formula_sum            'C16 H9 F6 N'
_chemical_formula_weight         329.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.8480(15)
_cell_length_b                   15.2591(14)
_cell_length_c                   24.008(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.003(2)
_cell_angle_gamma                90
_cell_volume                     5552.0(9)
_cell_formula_units_Z            16
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    49872
_cell_measurement_theta_min      1.77
_cell_measurement_theta_max      28.39

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_F_000             2656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.149
_shelx_estimated_absorpt_T_min   0.925
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.916
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            49872
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.774
_diffrn_reflns_theta_max         28.395
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6965
_reflns_number_gt                5373
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT-plus (Bruker, 2008)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2008)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 2012)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0513P)²+4.3997P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6965
_refine_ls_number_parameters     443
_refine_ls_number_restraints     51
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.1127
_refine_ls_wR_factor_gt          0.1011
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.14207(8) 0.12476(6) 0.38508(4) 0.0480(3) Uani 1 1 d . . . . .
F2 F 0.20064(7) 0.08624(6) 0.31947(5) 0.0457(3) Uani 1 1 d . . . . .
F3 F 0.06176(7) 0.08358(7) 0.30174(5) 0.0544(3) Uani 1 1 d . . . . .
F4 F 0.17601(6) 0.19662(6) 0.15122(4) 0.0371(2) Uani 1 1 d . . . . .
F5 F 0.03488(6) 0.19795(6) 0.12509(4) 0.0416(2) Uani 1 1 d . . . . .
F6 F 0.10555(7) 0.27189(6) 0.07730(4) 0.0430(2) Uani 1 1 d . . . . .
N1 N 0.11753(8) 0.23107(7) 0.25082(5) 0.0237(2) Uani 1 1 d . . . . .
C10 C 0.13293(10) 0.12918(9) 0.32835(6) 0.0276(3) Uani 1 1 d . . . . .
C1 C 0.12770(9) 0.22285(9) 0.30683(5) 0.0241(3) Uani 1 1 d . . . . .
C2 C 0.13466(9) 0.29200(9) 0.34627(6) 0.0268(3) Uani 1 1 d . . . . .
H3A H 0.1427 0.2808 0.3864 0.032 Uiso 1 1 calc R U . . .
C3 C 0.12959(9) 0.37673(9) 0.32549(6) 0.0256(3) Uani 1 1 d . . . . .
C4 C 0.11919(9) 0.38977(9) 0.26505(6) 0.0248(3) Uani 1 1 d . . . . .
C5 C 0.11503(10) 0.47426(9) 0.24005(6) 0.0310(3) Uani 1 1 d . . . . .
H6A H 0.1177 0.5247 0.2637 0.037 Uiso 1 1 calc R U . . .
C6 C 0.10723(11) 0.48372(10) 0.18247(7) 0.0352(3) Uani 1 1 d . . . . .
H7A H 0.1041 0.5407 0.1661 0.042 Uiso 1 1 calc R U . . .
C7 C 0.10382(10) 0.40936(10) 0.14695(6) 0.0318(3) Uani 1 1 d . . . . .
H8A H 0.0989 0.4169 0.1068 0.038 Uiso 1 1 calc R U . . .
C8 C 0.10746(9) 0.32666(9) 0.16946(6) 0.0254(3) Uani 1 1 d . . . . .
C9 C 0.11467(9) 0.31421(9) 0.22967(5) 0.0227(3) Uani 1 1 d . . . . .
C11 C 0.10590(10) 0.24840(10) 0.13139(6) 0.0283(3) Uani 1 1 d . . . . .
C12 C 0.13555(10) 0.44916(10) 0.36453(6) 0.0293(3) Uani 1 1 d . . . . .
C13 C 0.14189(11) 0.50554(10) 0.39926(6) 0.0315(3) Uani 1 1 d . . . . .
C14 C 0.15190(12) 0.57331(10) 0.44211(6) 0.0381(4) Uani 1 1 d . . . . .
H14A H 0.1734 0.5535 0.4836 0.046 Uiso 1 1 calc R U . . .
C15 C 0.09033(13) 0.65002(12) 0.43093(9) 0.0493(5) Uani 1 1 d . . . . .
H15A H 0.0435 0.6522 0.3932 0.059 Uiso 1 1 calc R U . . .
H15B H 0.0733 0.6743 0.4643 0.059 Uiso 1 1 calc R U . . .
C16 C 0.18186(13) 0.66234(11) 0.43032(8) 0.0451(4) Uani 1 1 d . . . . .
H16A H 0.2222 0.6944 0.4633 0.054 Uiso 1 1 calc R U . . .
H16B H 0.1925 0.6723 0.3922 0.054 Uiso 1 1 calc R U . . .
F1B F 0.13188(7) 0.76314(7) 0.28496(4) 0.0435(2) Uani 1 1 d . . . . .
F2B F 0.19190(6) 0.68732(6) 0.23174(4) 0.0363(2) Uani 1 1 d . . . . .
F3B F 0.05162(6) 0.70307(6) 0.20651(4) 0.0374(2) Uani 1 1 d . . . . .
F4B F 0.1358(10) 0.5823(8) 0.0665(6) 0.0557(19) Uani 0.50(4) 1 d D U P A 1
F5B F 0.1922(6) 0.6398(6) 0.0065(4) 0.0484(15) Uani 0.50(4) 1 d D U P A 1
F6B F 0.0541(6) 0.6325(9) -0.0137(5) 0.063(2) Uani 0.50(4) 1 d D U P A 1
N1B N 0.12813(8) 0.73931(7) 0.11179(5) 0.0240(2) Uani 1 1 d . . . . .
C1B C 0.12810(10) 0.74524(10) 0.22949(6) 0.0285(3) Uani 1 1 d . . . . .
C2B C 0.13510(9) 0.82695(9) 0.19630(5) 0.0261(3) Uani 1 1 d . . . . .
C3B C 0.14123(11) 0.90726(10) 0.22259(6) 0.0348(3) Uani 1 1 d . . . . .
H3B H 0.1442 0.9108 0.2626 0.042 Uiso 1 1 calc R U . . .
C4B C 0.14311(12) 0.98471(11) 0.19099(7) 0.0392(4) Uani 1 1 d . . . . .
H4B H 0.1482 1.0399 0.2100 0.047 Uiso 1 1 calc R U . . .
C5B C 0.13764(11) 0.98080(10) 0.13330(6) 0.0340(3) Uani 1 1 d . . . . .
H5B H 0.1380 1.0333 0.1121 0.041 Uiso 1 1 calc R U . . .
C6B C 0.13148(9) 0.89912(9) 0.10491(6) 0.0260(3) Uani 1 1 d . . . . .
C7B C 0.12498(10) 0.89249(9) 0.04444(6) 0.0273(3) Uani 1 1 d . . . . .
C8B C 0.12153(10) 0.81011(10) 0.02056(6) 0.0294(3) Uani 1 1 d . . . . .
H8B H 0.1173 0.8029 -0.0195 0.035 Uiso 1 1 calc R U . . .
C9B C 0.12433(9) 0.73708(9) 0.05640(6) 0.0254(3) Uani 1 1 d . . . . .
C10B C 0.13139(9) 0.82057(9) 0.13633(5) 0.0237(3) Uani 1 1 d . . . . .
C11B C 0.12486(10) 0.64733(10) 0.02983(6) 0.0302(3) Uani 1 1 d D . . . .
C12B C 0.12359(10) 0.96941(10) 0.01021(6) 0.0312(3) Uani 1 1 d . . . . .
C13B C 0.12400(10) 1.03327(10) -0.01844(6) 0.0312(3) Uani 1 1 d . . . . .
C14B C 0.12802(10) 1.10921(10) -0.05272(6) 0.0311(3) Uani 1 1 d . . . . .
H14B H 0.1265 1.1671 -0.0335 0.037 Uiso 1 1 calc R U . . .
C15B C 0.18459(11) 1.10481(11) -0.09388(7) 0.0355(3) Uani 1 1 d . . . . .
H15C H 0.2177 1.1581 -0.0982 0.043 Uiso 1 1 calc R U . . .
H15D H 0.2150 1.0489 -0.0962 0.043 Uiso 1 1 calc R U . . .
C16B C 0.08727(11) 1.10689(11) -0.11800(7) 0.0372(4) Uani 1 1 d . . . . .
H16C H 0.0572 1.0522 -0.1354 0.045 Uiso 1 1 calc R U . . .
H16D H 0.0599 1.1614 -0.1374 0.045 Uiso 1 1 calc R U . . .
F7B F 0.1993(7) 0.6327(8) 0.0190(9) 0.076(2) Uani 0.50(4) 1 d D U P A 2
F9B F 0.1112(17) 0.5834(9) 0.0629(6) 0.078(4) Uani 0.50(4) 1 d D U P A 2
F8B F 0.0629(7) 0.6404(8) -0.0201(3) 0.056(2) Uani 0.50(4) 1 d D U P A 2


_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 C10 1.3285(15) . ?
F2 C10 1.3267(17) . ?
F3 C10 1.3204(18) . ?
F4 C11 1.3327(17) . ?
F5 C11 1.3352(17) . ?
F6 C11 1.3456(15) . ?
N1 C1 1.3128(16) . ?
N1 C9 1.3623(17) . ?
C10 C1 1.5137(19) . ?
C1 C2 1.4004(19) . ?
C2 C3 1.380(2) . ?
C2 H3A 0.9500 . ?
C3 C4 1.4257(18) . ?
C3 C12 1.4342(19) . ?
C4 C5 1.4155(19) . ?
C4 C9 1.4215(18) . ?
C5 C6 1.359(2) . ?
C5 H6A 0.9500 . ?
C6 C7 1.411(2) . ?
C6 H7A 0.9500 . ?
C7 C8 1.367(2) . ?
C7 H8A 0.9500 . ?
C8 C9 1.4291(17) . ?
C8 C11 1.4994(19) . ?
C12 C13 1.182(2) . ?
C13 C14 1.434(2) . ?
C14 C16 1.493(2) . ?
C14 C15 1.497(2) . ?
C14 H14A 1.0000 . ?
C15 C16 1.467(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
F1B C1B 1.3435(15) . ?
F2B C1B 1.3321(17) . ?
F3B C1B 1.3403(18) . ?
F4B C11B 1.303(9) . ?
F5B C11B 1.347(6) . ?
F6B C11B 1.310(7) . ?
N1B C9B 1.3141(16) . ?
N1B C10B 1.3673(17) . ?
C1B C2B 1.501(2) . ?
C2B C3B 1.369(2) . ?
C2B C10B 1.4268(17) . ?
C3B C4B 1.409(2) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.364(2) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.4102(19) . ?
C5B H5B 0.9500 . ?
C6B C10B 1.4164(19) . ?
C6B C7B 1.4285(18) . ?
C7B C8B 1.376(2) . ?
C7B C12B 1.4293(19) . ?
C8B C9B 1.4006(19) . ?
C8B H8B 0.9500 . ?
C9B C11B 1.5119(19) . ?
C11B F7B 1.300(7) . ?
C11B F8B 1.313(6) . ?
C11B F9B 1.315(10) . ?
C12B C13B 1.194(2) . ?
C13B C14B 1.434(2) . ?
C14B C16B 1.511(2) . ?
C14B C15B 1.518(2) . ?
C14B H14B 1.0000 . ?
C15B C16B 1.481(2) . ?
C15B H15C 0.9900 . ?
C15B H15D 0.9900 . ?
C16B H16C 0.9900 . ?
C16B H16D 0.9900 . ?

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 C9 116.84(11) . . ?
F3 C10 F2 106.17(12) . . ?
F3 C10 F1 106.91(12) . . ?
F2 C10 F1 106.79(12) . . ?
F3 C10 C1 112.25(12) . . ?
F2 C10 C1 112.19(12) . . ?
F1 C10 C1 112.12(11) . . ?
N1 C1 C2 125.62(13) . . ?
N1 C1 C10 114.70(12) . . ?
C2 C1 C10 119.67(11) . . ?
C3 C2 C1 118.48(12) . . ?
C3 C2 H3A 120.8 . . ?
C1 C2 H3A 120.8 . . ?
C2 C3 C4 118.43(12) . . ?
C2 C3 C12 120.01(12) . . ?
C4 C3 C12 121.56(13) . . ?
C5 C4 C9 119.84(12) . . ?
C5 C4 C3 122.41(12) . . ?
C9 C4 C3 117.74(12) . . ?
C6 C5 C4 120.47(13) . . ?
C6 C5 H6A 119.8 . . ?
C4 C5 H6A 119.8 . . ?
C5 C6 C7 120.36(13) . . ?
C5 C6 H7A 119.8 . . ?
C7 C6 H7A 119.8 . . ?
C8 C7 C6 120.90(13) . . ?
C8 C7 H8A 119.5 . . ?
C6 C7 H8A 119.5 . . ?
C7 C8 C9 120.27(13) . . ?
C7 C8 C11 120.19(12) . . ?
C9 C8 C11 119.53(12) . . ?
N1 C9 C4 122.84(11) . . ?
N1 C9 C8 119.01(12) . . ?
C4 C9 C8 118.15(12) . . ?
F4 C11 F5 106.61(12) . . ?
F4 C11 F6 105.68(11) . . ?
F5 C11 F6 106.19(11) . . ?
F4 C11 C8 113.02(11) . . ?
F5 C11 C8 113.04(12) . . ?
F6 C11 C8 111.76(12) . . ?
C13 C12 C3 176.23(16) . . ?
C12 C13 C14 178.52(18) . . ?
C13 C14 C16 119.65(14) . . ?
C13 C14 C15 120.36(15) . . ?
C16 C14 C15 58.76(12) . . ?
C13 C14 H14A 115.4 . . ?
C16 C14 H14A 115.4 . . ?
C15 C14 H14A 115.4 . . ?
C16 C15 C14 60.49(12) . . ?
C16 C15 H15A 117.7 . . ?
C14 C15 H15A 117.7 . . ?
C16 C15 H15B 117.7 . . ?
C14 C15 H15B 117.7 . . ?
H15A C15 H15B 114.8 . . ?
C15 C16 C14 60.75(12) . . ?
C15 C16 H16A 117.7 . . ?
C14 C16 H16A 117.7 . . ?
C15 C16 H16B 117.7 . . ?
C14 C16 H16B 117.7 . . ?
H16A C16 H16B 114.8 . . ?
C9B N1B C10B 116.38(11) . . ?
F2B C1B F3B 106.42(12) . . ?
F2B C1B F1B 106.34(11) . . ?
F3B C1B F1B 106.16(11) . . ?
F2B C1B C2B 113.55(12) . . ?
F3B C1B C2B 112.25(11) . . ?
F1B C1B C2B 111.62(12) . . ?
C3B C2B C10B 120.18(13) . . ?
C3B C2B C1B 120.34(12) . . ?
C10B C2B C1B 119.42(12) . . ?
C2B C3B C4B 120.82(13) . . ?
C2B C3B H3B 119.6 . . ?
C4B C3B H3B 119.6 . . ?
C5B C4B C3B 120.33(14) . . ?
C5B C4B H4B 119.8 . . ?
C3B C4B H4B 119.8 . . ?
C4B C5B C6B 120.30(14) . . ?
C4B C5B H5B 119.9 . . ?
C6B C5B H5B 119.9 . . ?
C5B C6B C10B 120.07(12) . . ?
C5B C6B C7B 121.87(13) . . ?
C10B C6B C7B 118.06(12) . . ?
C8B C7B C6B 118.06(12) . . ?
C8B C7B C12B 121.24(12) . . ?
C6B C7B C12B 120.69(13) . . ?
C7B C8B C9B 118.73(12) . . ?
C7B C8B H8B 120.6 . . ?
C9B C8B H8B 120.6 . . ?
N1B C9B C8B 125.80(12) . . ?
N1B C9B C11B 116.50(12) . . ?
C8B C9B C11B 117.69(11) . . ?
N1B C10B C6B 122.93(11) . . ?
N1B C10B C2B 118.80(12) . . ?
C6B C10B C2B 118.27(12) . . ?
F4B C11B F6B 108.8(8) . . ?
F7B C11B F8B 106.5(8) . . ?
F7B C11B F9B 108.2(8) . . ?
F8B C11B F9B 106.3(9) . . ?
F4B C11B F5B 104.5(8) . . ?
F6B C11B F5B 104.5(7) . . ?
F7B C11B C9B 110.9(5) . . ?
F4B C11B C9B 114.9(7) . . ?
F6B C11B C9B 112.6(5) . . ?
F8B C11B C9B 111.3(5) . . ?
F9B C11B C9B 113.3(8) . . ?
F5B C11B C9B 110.8(4) . . ?
C13B C12B C7B 178.75(17) . . ?
C12B C13B C14B 177.75(17) . . ?
C13B C14B C16B 119.95(13) . . ?
C13B C14B C15B 118.16(13) . . ?
C16B C14B C15B 58.54(10) . . ?
C13B C14B H14B 116.0 . . ?
C16B C14B H14B 116.0 . . ?
C15B C14B H14B 116.0 . . ?
C16B C15B C14B 60.50(10) . . ?
C16B C15B H15C 117.7 . . ?
C14B C15B H15C 117.7 . . ?
C16B C15B H15D 117.7 . . ?
C14B C15B H15D 117.7 . . ?
H15C C15B H15D 114.8 . . ?
C15B C16B C14B 60.96(10) . . ?
C15B C16B H16C 117.7 . . ?
C14B C16B H16C 117.7 . . ?
C15B C16B H16D 117.7 . . ?
C14B C16B H16D 117.7 . . ?
H16C C16B H16D 114.8 . . ?

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
C9 N1 C1 C2 0.9(2) . . . . ?
C9 N1 C1 C10 -178.42(12) . . . . ?
F3 C10 C1 N1 -58.83(17) . . . . ?
F2 C10 C1 N1 60.64(17) . . . . ?
F1 C10 C1 N1 -179.20(12) . . . . ?
F3 C10 C1 C2 121.83(14) . . . . ?
F2 C10 C1 C2 -118.70(14) . . . . ?
F1 C10 C1 C2 1.46(19) . . . . ?
N1 C1 C2 C3 0.8(2) . . . . ?
C10 C1 C2 C3 -179.94(13) . . . . ?
C1 C2 C3 C4 -1.2(2) . . . . ?
C1 C2 C3 C12 179.37(13) . . . . ?
C2 C3 C4 C5 -178.80(14) . . . . ?
C12 C3 C4 C5 0.7(2) . . . . ?
C2 C3 C4 C9 0.0(2) . . . . ?
C12 C3 C4 C9 179.44(13) . . . . ?
C9 C4 C5 C6 -0.4(2) . . . . ?
C3 C4 C5 C6 178.39(14) . . . . ?
C4 C5 C6 C7 -0.5(2) . . . . ?
C5 C6 C7 C8 0.6(2) . . . . ?
C6 C7 C8 C9 0.1(2) . . . . ?
C6 C7 C8 C11 -178.56(14) . . . . ?
C1 N1 C9 C4 -2.2(2) . . . . ?
C1 N1 C9 C8 177.37(12) . . . . ?
C5 C4 C9 N1 -179.42(13) . . . . ?
C3 C4 C9 N1 1.8(2) . . . . ?
C5 C4 C9 C8 1.0(2) . . . . ?
C3 C4 C9 C8 -177.78(12) . . . . ?
C7 C8 C9 N1 179.53(13) . . . . ?
C11 C8 C9 N1 -1.8(2) . . . . ?
C7 C8 C9 C4 -0.9(2) . . . . ?
C11 C8 C9 C4 177.76(12) . . . . ?
C7 C8 C11 F4 122.38(15) . . . . ?
C9 C8 C11 F4 -56.29(17) . . . . ?
C7 C8 C11 F5 -116.41(15) . . . . ?
C9 C8 C11 F5 64.92(17) . . . . ?
C7 C8 C11 F6 3.32(19) . . . . ?
C9 C8 C11 F6 -175.35(12) . . . . ?
C13 C14 C15 C16 -108.37(18) . . . . ?
C13 C14 C16 C15 109.57(18) . . . . ?
F2B C1B C2B C3B -122.30(15) . . . . ?
F3B C1B C2B C3B 116.94(15) . . . . ?
F1B C1B C2B C3B -2.1(2) . . . . ?
F2B C1B C2B C10B 60.45(17) . . . . ?
F3B C1B C2B C10B -60.30(17) . . . . ?
F1B C1B C2B C10B -179.35(13) . . . . ?
C10B C2B C3B C4B 0.6(2) . . . . ?
C1B C2B C3B C4B -176.61(15) . . . . ?
C2B C3B C4B C5B 0.9(3) . . . . ?
C3B C4B C5B C6B -1.0(3) . . . . ?
C4B C5B C6B C10B -0.3(2) . . . . ?
C4B C5B C6B C7B 179.52(15) . . . . ?
C5B C6B C7B C8B 178.34(14) . . . . ?
C10B C6B C7B C8B -1.8(2) . . . . ?
C5B C6B C7B C12B -0.6(2) . . . . ?
C10B C6B C7B C12B 179.20(13) . . . . ?
C6B C7B C8B C9B 0.1(2) . . . . ?
C12B C7B C8B C9B 179.13(14) . . . . ?
C10B N1B C9B C8B -1.4(2) . . . . ?
C10B N1B C9B C11B 177.34(12) . . . . ?
C7B C8B C9B N1B 1.6(2) . . . . ?
C7B C8B C9B C11B -177.13(14) . . . . ?
C9B N1B C10B C6B -0.5(2) . . . . ?
C9B N1B C10B C2B 179.66(13) . . . . ?
C5B C6B C10B N1B -178.08(14) . . . . ?
C7B C6B C10B N1B 2.1(2) . . . . ?
C5B C6B C10B C2B 1.8(2) . . . . ?
C7B C6B C10B C2B -178.08(13) . . . . ?
C3B C2B C10B N1B 177.94(13) . . . . ?
C1B C2B C10B N1B -4.8(2) . . . . ?
C3B C2B C10B C6B -1.9(2) . . . . ?
C1B C2B C10B C6B 175.34(13) . . . . ?
N1B C9B C11B F7B -109.0(10) . . . . ?
C8B C9B C11B F7B 69.9(10) . . . . ?
N1B C9B C11B F4B -5.0(8) . . . . ?
C8B C9B C11B F4B 173.9(8) . . . . ?
N1B C9B C11B F6B 120.3(8) . . . . ?
C8B C9B C11B F6B -60.9(8) . . . . ?
N1B C9B C11B F8B 132.6(6) . . . . ?
C8B C9B C11B F8B -48.5(6) . . . . ?
N1B C9B C11B F9B 13.0(12) . . . . ?
C8B C9B C11B F9B -168.2(12) . . . . ?
N1B C9B C11B F5B -123.1(4) . . . . ?
C8B C9B C11B F5B 55.8(4) . . . . ?
C13B C14B C15B C16B 109.66(16) . . . . ?
C13B C14B C16B C15B -106.62(16) . . . . ?

_refine_diff_density_max         0.400
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.044

_shelxl_version_number           2014-3

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform'
####################################################################### 
# 
# 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_4M
_database_code_depnum_ccdc_archive 'CCDC 1585042'
_audit_update_record             
;
2017-11-10 deposited with the CCDC.
2018-03-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H11 F6 N'
_chemical_formula_sum            'C20 H11 F6 N'
_chemical_formula_weight         379.30

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6056(4)
_cell_length_b                   9.6645(3)
_cell_length_c                   18.9511(9)
_cell_angle_alpha                102.4830(10)
_cell_angle_beta                 100.815(2)
_cell_angle_gamma                90.058(3)
_cell_volume                     1685.61(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9985
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      28.26

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.134
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21236
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.160
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             6222
_reflns_number_gt                5114
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT-plus (Bruker, 2008)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2008)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 2012)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0714P)²+1.3703P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6222
_refine_ls_number_parameters     502
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1418
_refine_ls_wR_factor_gt          0.1321
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F7 F 1.45179(16) 0.92432(17) 1.20823(8) 0.0479(4) Uani 1 1 d . . . . .
F8 F 1.50604(18) 0.74129(16) 1.13173(12) 0.0732(6) Uani 1 1 d . . . . .
F9 F 1.50706(15) 0.94680(17) 1.10723(9) 0.0488(4) Uani 1 1 d . . . . .
F1 F 0.51879(15) 0.89102(15) 0.37561(9) 0.0463(4) Uani 1 1 d . . . . .
F6 F 1.54716(18) 0.54844(16) 0.85582(10) 0.0594(5) Uani 1 1 d . . . . .
F5 F 1.44729(16) 0.7238(2) 0.91565(7) 0.0546(5) Uani 1 1 d . . . . .
F2 F 0.74176(16) 0.93858(15) 0.40022(9) 0.0484(4) Uani 1 1 d . . . . .
F3 F 0.65052(19) 0.79254(16) 0.30130(8) 0.0529(4) Uani 1 1 d . . . . .
F4 F 1.59069(15) 0.75833(17) 0.84777(8) 0.0449(4) Uani 1 1 d . . . . .
C40 C 0.8820(2) 0.0565(2) 0.62991(12) 0.0310(5) Uani 1 1 d D . . . .
C37 C 0.9148(2) 0.1661(2) 0.70028(11) 0.0233(4) Uani 1 1 d . . . . .
C38 C 0.8192(2) 0.2715(2) 0.71572(12) 0.0271(5) Uani 1 1 d . . . . .
H38 H 0.7313 0.2712 0.6829 0.033 Uiso 1 1 calc R U . . .
C39 C 0.8536(2) 0.3766(2) 0.77933(12) 0.0266(5) Uani 1 1 d . . . . .
H39 H 0.7888 0.4489 0.7900 0.032 Uiso 1 1 calc R U . . .
C34 C 0.9820(2) 0.3777(2) 0.82801(11) 0.0229(4) Uani 1 1 d . . . . .
C33 C 1.0214(2) 0.4908(2) 0.89169(11) 0.0245(4) Uani 1 1 d . . . . .
C32 C 1.0567(2) 0.5878(2) 0.94375(11) 0.0235(4) Uani 1 1 d . . . . .
C23 C 1.1028(2) 0.7041(2) 1.00490(11) 0.0216(4) Uani 1 1 d . . . . .
C24 C 1.0056(2) 0.8076(2) 1.02949(11) 0.0207(4) Uani 1 1 d . . . . .
C25 C 0.8597(2) 0.7991(2) 0.99786(11) 0.0245(4) Uani 1 1 d . . . . .
H25 H 0.8216 0.7219 0.9585 0.029 Uiso 1 1 calc R U . . .
C26 C 0.7736(2) 0.9023(2) 1.02396(12) 0.0276(5) Uani 1 1 d . . . . .
H26 H 0.6753 0.8961 1.0028 0.033 Uiso 1 1 calc R U . . .
C27 C 0.8287(2) 1.0178(2) 1.08201(12) 0.0271(5) Uani 1 1 d . . . . .
H27 H 0.7666 1.0883 1.0990 0.033 Uiso 1 1 calc R U . . .
C30 C 1.4367(3) 0.8611(2) 1.13708(14) 0.0360(6) Uani 1 1 d . . . . .
C21 C 1.2836(2) 0.8374(2) 1.09877(12) 0.0252(4) Uani 1 1 d . . . . .
C22 C 1.2421(2) 0.7193(2) 1.04039(12) 0.0244(4) Uani 1 1 d . . . . .
H22 H 1.3088 0.6516 1.0258 0.029 Uiso 1 1 calc R U . . .
C29 C 1.0610(2) 0.9236(2) 1.08862(11) 0.0210(4) Uani 1 1 d . . . . .
N2 N 1.20006(18) 0.93691(17) 1.12269(9) 0.0232(4) Uani 1 1 d . . . . .
C28 C 0.9693(2) 1.0314(2) 1.11460(11) 0.0231(4) Uani 1 1 d . . . . .
C31 C 1.0290(2) 1.1546(2) 1.17628(12) 0.0292(5) Uani 1 1 d . . . . .
H31A H 0.9545 1.2217 1.1852 0.044 Uiso 1 1 calc R U . . .
H31B H 1.1070 1.2022 1.1628 0.044 Uiso 1 1 calc R U . . .
H31C H 1.0645 1.1202 1.2211 0.044 Uiso 1 1 calc R U . . .
C36 C 1.0417(2) 0.1642(2) 0.74915(11) 0.0229(4) Uani 1 1 d . . . . .
H36 H 1.1054 0.0908 0.7388 0.027 Uiso 1 1 calc R U . . .
C35 C 1.0758(2) 0.2689(2) 0.81289(11) 0.0233(4) Uani 1 1 d . . . . .
H35 H 1.1624 0.2671 0.8464 0.028 Uiso 1 1 calc R U . . .
C10 C 0.6431(2) 0.8336(2) 0.37237(12) 0.0277(5) Uani 1 1 d . . . . .
C1 C 0.6655(2) 0.7126(2) 0.41139(11) 0.0214(4) Uani 1 1 d . . . . .
C2 C 0.7836(2) 0.7158(2) 0.46772(11) 0.0213(4) Uani 1 1 d . . . . .
H2 H 0.8496 0.7947 0.4828 0.026 Uiso 1 1 calc R U . . .
C3 C 0.8019(2) 0.6018(2) 0.50083(11) 0.0198(4) Uani 1 1 d . . . . .
C12 C 0.9189(2) 0.6033(2) 0.56010(11) 0.0211(4) Uani 1 1 d . . . . .
C13 C 1.0165(2) 0.6122(2) 0.61101(11) 0.0213(4) Uani 1 1 d . . . . .
C14 C 1.1344(2) 0.6266(2) 0.67122(10) 0.0201(4) Uani 1 1 d . . . . .
C15 C 1.2261(2) 0.7465(2) 0.69013(11) 0.0227(4) Uani 1 1 d . . . . .
H15 H 1.2100 0.8189 0.6630 0.027 Uiso 1 1 calc R U . . .
C16 C 1.3403(2) 0.7606(2) 0.74821(11) 0.0239(4) Uani 1 1 d . . . . .
H16 H 1.4024 0.8425 0.7609 0.029 Uiso 1 1 calc R U . . .
C17 C 1.3639(2) 0.6550(2) 0.78779(11) 0.0236(4) Uani 1 1 d . . . . .
C20 C 1.4858(2) 0.6703(2) 0.85145(12) 0.0297(5) Uani 1 1 d . . . . .
N1 N 0.56793(18) 0.60912(17) 0.38683(9) 0.0218(4) Uani 1 1 d . . . . .
C9 C 0.5847(2) 0.4941(2) 0.41800(11) 0.0198(4) Uani 1 1 d . . . . .
C4 C 0.7018(2) 0.4842(2) 0.47520(10) 0.0193(4) Uani 1 1 d . . . . .
C5 C 0.7153(2) 0.3602(2) 0.50350(11) 0.0238(4) Uani 1 1 d . . . . .
H5 H 0.7936 0.3524 0.5412 0.029 Uiso 1 1 calc R U . . .
C6 C 0.6157(2) 0.2518(2) 0.47657(12) 0.0273(5) Uani 1 1 d . . . . .
H6 H 0.6249 0.1686 0.4958 0.033 Uiso 1 1 calc R U . . .
C7 C 0.4993(2) 0.2617(2) 0.42045(12) 0.0271(5) Uani 1 1 d . . . . .
H7 H 0.4314 0.1845 0.4027 0.032 Uiso 1 1 calc R U . . .
C8 C 0.4808(2) 0.3791(2) 0.39067(11) 0.0226(4) Uani 1 1 d . . . . .
C11 C 0.3572(2) 0.3890(2) 0.33076(12) 0.0288(5) Uani 1 1 d . . . . .
H11A H 0.3054 0.2968 0.3132 0.043 Uiso 1 1 calc R U . . .
H11B H 0.3916 0.4158 0.2899 0.043 Uiso 1 1 calc R U . . .
H11C H 0.2938 0.4607 0.3500 0.043 Uiso 1 1 calc R U . . .
C19 C 1.1600(2) 0.5205(2) 0.71142(11) 0.0240(4) Uani 1 1 d . . . . .
H19 H 1.0985 0.4382 0.6988 0.029 Uiso 1 1 calc R U . . .
C18 C 1.2738(2) 0.5350(2) 0.76907(11) 0.0251(4) Uani 1 1 d . . . . .
H18 H 1.2907 0.4626 0.7961 0.030 Uiso 1 1 calc R U . . .
F11A F 0.9239(2) 0.10730(19) 0.57348(9) 0.0492(6) Uani 0.850(4) 1 d . . P A 1
F10A F 0.74687(17) 0.0271(2) 0.60397(11) 0.0501(6) Uani 0.850(4) 1 d . . P A 1
F12A F 0.9549(2) -0.05697(18) 0.63041(10) 0.0589(7) Uani 0.850(4) 1 d . . P A 1
F10B F 0.8273(10) -0.0537(7) 0.6463(6) 0.065(4) Uiso 0.150(4) 1 d D . P A 2
F12B F 0.7881(8) 0.0890(11) 0.5779(4) 0.064(4) Uiso 0.150(4) 1 d D . P A 2
F11B F 0.9889(7) 0.0107(11) 0.5999(5) 0.070(4) Uiso 0.150(4) 1 d D . P A 2


_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
F7 C30 1.335(3) . ?
F8 C30 1.331(3) . ?
F9 C30 1.345(3) . ?
F1 C10 1.323(2) . ?
F6 C20 1.329(3) . ?
F5 C20 1.335(3) . ?
F2 C10 1.337(3) . ?
F3 C10 1.335(3) . ?
F4 C20 1.340(3) . ?
C40 F11B 1.298(2) . ?
C40 F12B 1.299(2) . ?
C40 F12A 1.302(3) . ?
C40 F10A 1.306(3) . ?
C40 F10B 1.307(2) . ?
C40 F11A 1.391(3) . ?
C40 C37 1.493(3) . ?
C37 C36 1.389(3) . ?
C37 C38 1.393(3) . ?
C38 C39 1.384(3) . ?
C38 H38 0.9500 . ?
C39 C34 1.394(3) . ?
C39 H39 0.9500 . ?
C34 C35 1.403(3) . ?
C34 C33 1.432(3) . ?
C33 C32 1.201(3) . ?
C32 C23 1.430(3) . ?
C23 C22 1.373(3) . ?
C23 C24 1.432(3) . ?
C24 C25 1.412(3) . ?
C24 C29 1.424(3) . ?
C25 C26 1.366(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.410(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.368(3) . ?
C27 H27 0.9500 . ?
C30 C21 1.506(3) . ?
C21 N2 1.313(3) . ?
C21 C22 1.405(3) . ?
C22 H22 0.9500 . ?
C29 N2 1.363(3) . ?
C29 C28 1.431(3) . ?
C28 C31 1.503(3) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C36 C35 1.383(3) . ?
C36 H36 0.9500 . ?
C35 H35 0.9500 . ?
C10 C1 1.508(3) . ?
C1 N1 1.315(3) . ?
C1 C2 1.400(3) . ?
C2 C3 1.377(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.427(3) . ?
C3 C12 1.430(3) . ?
C12 C13 1.201(3) . ?
C13 C14 1.432(3) . ?
C14 C15 1.395(3) . ?
C14 C19 1.400(3) . ?
C15 C16 1.384(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.388(3) . ?
C17 C20 1.497(3) . ?
N1 C9 1.364(3) . ?
C9 C4 1.428(3) . ?
C9 C8 1.433(3) . ?
C4 C5 1.411(3) . ?
C5 C6 1.363(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.411(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.370(3) . ?
C7 H7 0.9500 . ?
C8 C11 1.500(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C19 C18 1.376(3) . ?
C19 H19 0.9500 . ?
C18 H18 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
F11B C40 F12B 106.1(2) . . ?
F12A C40 F10A 112.6(2) . . ?
F11B C40 F10B 105.8(2) . . ?
F12B C40 F10B 105.7(2) . . ?
F12A C40 F11A 102.2(2) . . ?
F10A C40 F11A 101.8(2) . . ?
F11B C40 C37 116.6(5) . . ?
F12B C40 C37 115.9(5) . . ?
F12A C40 C37 113.97(19) . . ?
F10A C40 C37 114.70(18) . . ?
F10B C40 C37 105.8(5) . . ?
F11A C40 C37 110.11(18) . . ?
C36 C37 C38 120.37(19) . . ?
C36 C37 C40 119.86(18) . . ?
C38 C37 C40 119.76(19) . . ?
C39 C38 C37 119.4(2) . . ?
C39 C38 H38 120.3 . . ?
C37 C38 H38 120.3 . . ?
C38 C39 C34 120.80(19) . . ?
C38 C39 H39 119.6 . . ?
C34 C39 H39 119.6 . . ?
C39 C34 C35 119.34(18) . . ?
C39 C34 C33 120.89(18) . . ?
C35 C34 C33 119.73(19) . . ?
C32 C33 C34 177.9(2) . . ?
C33 C32 C23 178.1(2) . . ?
C22 C23 C32 120.22(18) . . ?
C22 C23 C24 118.89(18) . . ?
C32 C23 C24 120.89(19) . . ?
C25 C24 C29 119.41(18) . . ?
C25 C24 C23 123.08(19) . . ?
C29 C24 C23 117.51(18) . . ?
C26 C25 C24 119.80(19) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C25 C26 C27 120.7(2) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 H26 119.6 . . ?
C28 C27 C26 121.91(19) . . ?
C28 C27 H27 119.0 . . ?
C26 C27 H27 119.0 . . ?
F8 C30 F7 108.5(2) . . ?
F8 C30 F9 105.9(2) . . ?
F7 C30 F9 105.55(19) . . ?
F8 C30 C21 112.48(19) . . ?
F7 C30 C21 112.7(2) . . ?
F9 C30 C21 111.2(2) . . ?
N2 C21 C22 125.5(2) . . ?
N2 C21 C30 114.52(19) . . ?
C22 C21 C30 119.90(19) . . ?
C23 C22 C21 118.27(19) . . ?
C23 C22 H22 120.9 . . ?
C21 C22 H22 120.9 . . ?
N2 C29 C24 122.52(18) . . ?
N2 C29 C28 117.56(18) . . ?
C24 C29 C28 119.92(19) . . ?
C21 N2 C29 117.27(18) . . ?
C27 C28 C29 118.22(19) . . ?
C27 C28 C31 122.21(19) . . ?
C29 C28 C31 119.58(19) . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C35 C36 C37 120.26(18) . . ?
C35 C36 H36 119.9 . . ?
C37 C36 H36 119.9 . . ?
C36 C35 C34 119.84(19) . . ?
C36 C35 H35 120.1 . . ?
C34 C35 H35 120.1 . . ?
F1 C10 F3 107.28(19) . . ?
F1 C10 F2 106.58(17) . . ?
F3 C10 F2 105.34(18) . . ?
F1 C10 C1 112.78(18) . . ?
F3 C10 C1 111.84(17) . . ?
F2 C10 C1 112.55(18) . . ?
N1 C1 C2 125.53(19) . . ?
N1 C1 C10 114.21(18) . . ?
C2 C1 C10 120.25(18) . . ?
C3 C2 C1 118.43(18) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 118.78(18) . . ?
C2 C3 C12 119.93(18) . . ?
C4 C3 C12 121.28(18) . . ?
C13 C12 C3 176.6(2) . . ?
C12 C13 C14 178.3(2) . . ?
C15 C14 C19 119.16(19) . . ?
C15 C14 C13 120.20(18) . . ?
C19 C14 C13 120.64(18) . . ?
C16 C15 C14 120.34(19) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.87(19) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C18 120.19(19) . . ?
C16 C17 C20 120.31(19) . . ?
C18 C17 C20 119.49(19) . . ?
F6 C20 F5 108.3(2) . . ?
F6 C20 F4 104.75(18) . . ?
F5 C20 F4 105.17(18) . . ?
F6 C20 C17 112.80(18) . . ?
F5 C20 C17 112.17(18) . . ?
F4 C20 C17 113.11(19) . . ?
C1 N1 C9 117.18(17) . . ?
N1 C9 C4 122.44(18) . . ?
N1 C9 C8 117.82(18) . . ?
C4 C9 C8 119.73(18) . . ?
C5 C4 C3 122.78(19) . . ?
C5 C4 C9 119.62(18) . . ?
C3 C4 C9 117.60(18) . . ?
C6 C5 C4 119.8(2) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 120.8(2) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C6 122.1(2) . . ?
C8 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C7 C8 C9 118.03(19) . . ?
C7 C8 C11 121.96(19) . . ?
C9 C8 C11 120.01(19) . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C18 C19 C14 120.29(19) . . ?
C18 C19 H19 119.9 . . ?
C14 C19 H19 119.9 . . ?
C19 C18 C17 120.2(2) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F11B C40 C37 C36 -32.7(5) . . . . ?
F12B C40 C37 C36 -158.8(5) . . . . ?
F12A C40 C37 C36 20.2(3) . . . . ?
F10A C40 C37 C36 152.0(2) . . . . ?
F10B C40 C37 C36 84.5(5) . . . . ?
F11A C40 C37 C36 -93.9(2) . . . . ?
F11B C40 C37 C38 145.8(5) . . . . ?
F12B C40 C37 C38 19.7(5) . . . . ?
F12A C40 C37 C38 -161.2(2) . . . . ?
F10A C40 C37 C38 -29.4(3) . . . . ?
F10B C40 C37 C38 -97.0(5) . . . . ?
F11A C40 C37 C38 84.7(2) . . . . ?
C36 C37 C38 C39 1.7(3) . . . . ?
C40 C37 C38 C39 -176.9(2) . . . . ?
C37 C38 C39 C34 -0.2(3) . . . . ?
C38 C39 C34 C35 -1.5(3) . . . . ?
C38 C39 C34 C33 176.4(2) . . . . ?
C22 C23 C24 C25 -178.25(19) . . . . ?
C32 C23 C24 C25 2.7(3) . . . . ?
C22 C23 C24 C29 1.8(3) . . . . ?
C32 C23 C24 C29 -177.28(18) . . . . ?
C29 C24 C25 C26 0.3(3) . . . . ?
C23 C24 C25 C26 -179.63(19) . . . . ?
C24 C25 C26 C27 0.3(3) . . . . ?
C25 C26 C27 C28 -0.3(3) . . . . ?
F8 C30 C21 N2 157.4(2) . . . . ?
F7 C30 C21 N2 34.4(3) . . . . ?
F9 C30 C21 N2 -84.0(2) . . . . ?
F8 C30 C21 C22 -25.3(3) . . . . ?
F7 C30 C21 C22 -148.3(2) . . . . ?
F9 C30 C21 C22 93.4(2) . . . . ?
C32 C23 C22 C21 178.13(18) . . . . ?
C24 C23 C22 C21 -1.0(3) . . . . ?
N2 C21 C22 C23 -0.4(3) . . . . ?
C30 C21 C22 C23 -177.49(19) . . . . ?
C25 C24 C29 N2 178.64(18) . . . . ?
C23 C24 C29 N2 -1.4(3) . . . . ?
C25 C24 C29 C28 -1.0(3) . . . . ?
C23 C24 C29 C28 178.93(17) . . . . ?
C22 C21 N2 C29 0.9(3) . . . . ?
C30 C21 N2 C29 178.06(18) . . . . ?
C24 C29 N2 C21 0.1(3) . . . . ?
C28 C29 N2 C21 179.76(18) . . . . ?
C26 C27 C28 C29 -0.4(3) . . . . ?
C26 C27 C28 C31 179.71(19) . . . . ?
N2 C29 C28 C27 -178.60(18) . . . . ?
C24 C29 C28 C27 1.1(3) . . . . ?
N2 C29 C28 C31 1.3(3) . . . . ?
C24 C29 C28 C31 -179.08(18) . . . . ?
C38 C37 C36 C35 -1.4(3) . . . . ?
C40 C37 C36 C35 177.15(19) . . . . ?
C37 C36 C35 C34 -0.4(3) . . . . ?
C39 C34 C35 C36 1.8(3) . . . . ?
C33 C34 C35 C36 -176.11(18) . . . . ?
F1 C10 C1 N1 57.5(2) . . . . ?
F3 C10 C1 N1 -63.5(2) . . . . ?
F2 C10 C1 N1 178.11(17) . . . . ?
F1 C10 C1 C2 -123.5(2) . . . . ?
F3 C10 C1 C2 115.5(2) . . . . ?
F2 C10 C1 C2 -2.8(3) . . . . ?
N1 C1 C2 C3 0.4(3) . . . . ?
C10 C1 C2 C3 -178.57(17) . . . . ?
C1 C2 C3 C4 1.5(3) . . . . ?
C1 C2 C3 C12 -178.08(17) . . . . ?
C19 C14 C15 C16 -0.4(3) . . . . ?
C13 C14 C15 C16 -179.86(17) . . . . ?
C14 C15 C16 C17 0.1(3) . . . . ?
C15 C16 C17 C18 0.3(3) . . . . ?
C15 C16 C17 C20 -179.02(18) . . . . ?
C16 C17 C20 F6 -142.3(2) . . . . ?
C18 C17 C20 F6 38.3(3) . . . . ?
C16 C17 C20 F5 95.1(2) . . . . ?
C18 C17 C20 F5 -84.2(2) . . . . ?
C16 C17 C20 F4 -23.6(3) . . . . ?
C18 C17 C20 F4 157.01(18) . . . . ?
C2 C1 N1 C9 -1.3(3) . . . . ?
C10 C1 N1 C9 177.72(16) . . . . ?
C1 N1 C9 C4 0.3(3) . . . . ?
C1 N1 C9 C8 -178.66(16) . . . . ?
C2 C3 C4 C5 177.11(17) . . . . ?
C12 C3 C4 C5 -3.3(3) . . . . ?
C2 C3 C4 C9 -2.3(3) . . . . ?
C12 C3 C4 C9 177.28(16) . . . . ?
N1 C9 C4 C5 -177.99(17) . . . . ?
C8 C9 C4 C5 1.0(3) . . . . ?
N1 C9 C4 C3 1.4(3) . . . . ?
C8 C9 C4 C3 -179.63(16) . . . . ?
C3 C4 C5 C6 179.92(18) . . . . ?
C9 C4 C5 C6 -0.7(3) . . . . ?
C4 C5 C6 C7 0.2(3) . . . . ?
C5 C6 C7 C8 0.0(3) . . . . ?
C6 C7 C8 C9 0.2(3) . . . . ?
C6 C7 C8 C11 179.71(18) . . . . ?
N1 C9 C8 C7 178.29(17) . . . . ?
C4 C9 C8 C7 -0.7(3) . . . . ?
N1 C9 C8 C11 -1.2(3) . . . . ?
C4 C9 C8 C11 179.78(17) . . . . ?
C15 C14 C19 C18 0.3(3) . . . . ?
C13 C14 C19 C18 179.79(18) . . . . ?
C14 C19 C18 C17 0.1(3) . . . . ?
C16 C17 C18 C19 -0.4(3) . . . . ?
C20 C17 C18 C19 178.97(18) . . . . ?

_refine_diff_density_max         0.773
_refine_diff_density_min         -0.632
_refine_diff_density_rms         0.058

_shelxl_version_number           2014-3

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform'
####################################################################### 
# 
# 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_4N
_database_code_depnum_ccdc_archive 'CCDC 1585043'
_audit_update_record             
;
2017-11-10 deposited with the CCDC.
2018-03-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H12 F3 N'
_chemical_formula_sum            'C16 H12 F3 N'
_chemical_formula_weight         275.27

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5758(3)
_cell_length_b                   11.2809(5)
_cell_length_c                   16.6769(9)
_cell_angle_alpha                103.657(3)
_cell_angle_beta                 101.408(3)
_cell_angle_gamma                105.290(2)
_cell_volume                     1283.47(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9961
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      28.24

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.114
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17282
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.965
_diffrn_reflns_theta_max         28.429
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6132
_reflns_number_gt                4635
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT-plus (Bruker, 2008)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2008)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0595P)²+0.2560P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6132
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1159
_refine_ls_wR_factor_gt          0.1053
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.61242(16) 0.18803(11) 0.86462(8) 0.0171(3) Uani 1 1 d . . . . .
C2 C 0.63098(16) 0.31961(11) 0.88841(8) 0.0180(3) Uani 1 1 d . . . . .
H2 H 0.617158 0.361227 0.942281 0.022 Uiso 1 1 calc R U . . .
C3 C 0.66993(16) 0.38672(11) 0.83119(8) 0.0176(3) Uani 1 1 d . . . . .
C4 C 0.68635(16) 0.31877(11) 0.75080(8) 0.0167(2) Uani 1 1 d . . . . .
C5 C 0.72307(17) 0.37967(12) 0.68786(8) 0.0206(3) Uani 1 1 d . . . . .
H5 H 0.739433 0.468996 0.698770 0.025 Uiso 1 1 calc R U . . .
C6 C 0.73486(18) 0.30957(13) 0.61150(8) 0.0232(3) Uani 1 1 d . . . . .
H6 H 0.758314 0.350505 0.569201 0.028 Uiso 1 1 calc R U . . .
C7 C 0.71269(17) 0.17713(13) 0.59453(8) 0.0219(3) Uani 1 1 d . . . . .
H7 H 0.721424 0.130561 0.540807 0.026 Uiso 1 1 calc R U . . .
C8 C 0.67871(16) 0.11360(12) 0.65383(8) 0.0186(3) Uani 1 1 d . . . . .
C9 C 0.66367(16) 0.18493(11) 0.73357(8) 0.0164(2) Uani 1 1 d . . . . .
C10 C 0.57668(18) 0.11156(12) 0.92646(8) 0.0199(3) Uani 1 1 d . . . . .
C11 C 0.66012(18) -0.02659(12) 0.63616(8) 0.0225(3) Uani 1 1 d . . . . .
H11A H 0.646357 -0.064689 0.575094 0.034 Uiso 1 1 calc R U . . .
H11B H 0.547712 -0.071598 0.651083 0.034 Uiso 1 1 calc R U . . .
H11C H 0.774168 -0.034998 0.670770 0.034 Uiso 1 1 calc R U . . .
C12 C 0.69475(17) 0.52202(12) 0.85212(8) 0.0193(3) Uani 1 1 d . . . . .
C13 C 0.71938(17) 0.63523(12) 0.86759(8) 0.0202(3) Uani 1 1 d . . . . .
C14 C 0.75189(18) 0.77128(12) 0.88330(8) 0.0214(3) Uani 1 1 d . . . . .
H14 H 0.703674 0.813936 0.930001 0.026 Uiso 1 1 calc R U . . .
C16 C 0.74794(19) 0.82453(13) 0.80783(9) 0.0252(3) Uani 1 1 d . . . . .
H16A H 0.722145 0.763030 0.750299 0.030 Uiso 1 1 calc R U . . .
H16B H 0.695129 0.896068 0.808226 0.030 Uiso 1 1 calc R U . . .
C17 C 0.93390(19) 0.85273(13) 0.87155(9) 0.0266(3) Uani 1 1 d . . . . .
H17A H 0.995779 0.941630 0.911306 0.032 Uiso 1 1 calc R U . . .
H17B H 1.022799 0.808572 0.853370 0.032 Uiso 1 1 calc R U . . .
C18 C 0.75421(16) 0.66127(12) 0.37548(8) 0.0178(3) Uani 1 1 d . . . . .
C19 C 0.77786(17) 0.79357(12) 0.39981(8) 0.0188(3) Uani 1 1 d . . . . .
H19 H 0.768228 0.836385 0.454323 0.023 Uiso 1 1 calc R U . . .
C20 C 0.81563(16) 0.85940(11) 0.34178(8) 0.0176(3) Uani 1 1 d . . . . .
C21 C 0.83266(16) 0.79155(11) 0.26172(8) 0.0171(3) Uani 1 1 d . . . . .
C22 C 0.87065(17) 0.85128(12) 0.19826(8) 0.0206(3) Uani 1 1 d . . . . .
H22 H 0.885733 0.940306 0.208222 0.025 Uiso 1 1 calc R U . . .
C23 C 0.88547(18) 0.78035(13) 0.12280(9) 0.0234(3) Uani 1 1 d . . . . .
H23 H 0.910376 0.820523 0.080308 0.028 Uiso 1 1 calc R U . . .
C24 C 0.86428(17) 0.64823(13) 0.10711(8) 0.0223(3) Uani 1 1 d . . . . .
H24 H 0.875448 0.601138 0.054098 0.027 Uiso 1 1 calc R U . . .
C25 C 0.82789(17) 0.58585(12) 0.16651(8) 0.0192(3) Uani 1 1 d . . . . .
C26 C 0.80979(16) 0.65776(11) 0.24533(8) 0.0169(2) Uani 1 1 d . . . . .
C27 C 0.70551(18) 0.58314(12) 0.43513(9) 0.0221(3) Uani 1 1 d . . . . .
C29 C 0.80799(19) 0.44558(12) 0.15032(9) 0.0231(3) Uani 1 1 d . . . . .
H29A H 0.837238 0.413209 0.096296 0.035 Uiso 1 1 calc R U . . .
H29B H 0.677190 0.396651 0.146475 0.035 Uiso 1 1 calc R U . . .
H29C H 0.896569 0.435345 0.197625 0.035 Uiso 1 1 calc R U . . .
C30 C 0.83178(17) 0.99345(12) 0.36039(8) 0.0207(3) Uani 1 1 d . . . . .
C31 C 0.83590(17) 1.10295(12) 0.37057(8) 0.0211(3) Uani 1 1 d . . . . .
C32 C 0.83442(18) 1.23205(12) 0.37716(9) 0.0223(3) Uani 1 1 d . . . . .
H32 H 0.815326 1.281024 0.431320 0.027 Uiso 1 1 calc R U . . .
C33 C 0.7500(2) 1.25848(13) 0.29557(9) 0.0311(3) Uani 1 1 d . . . . .
H33A H 0.700267 1.185753 0.241559 0.037 Uiso 1 1 calc R U . . .
H33B H 0.678209 1.320359 0.300011 0.037 Uiso 1 1 calc R U . . .
C34 C 0.9585(2) 1.31022(13) 0.33466(9) 0.0269(3) Uani 1 1 d . . . . .
H34A H 1.016459 1.404335 0.363354 0.032 Uiso 1 1 calc R U . . .
H34B H 1.038513 1.269755 0.304913 0.032 Uiso 1 1 calc R U . . .
N1 N 0.62780(14) 0.12110(9) 0.79195(6) 0.0168(2) Uani 1 1 d . . . . .
N2 N 0.76922(14) 0.59370(9) 0.30288(7) 0.0177(2) Uani 1 1 d . . . . .
F1 F 0.54261(13) 0.17836(7) 0.99555(5) 0.0337(2) Uani 1 1 d . . . . .
F2 F 0.72666(12) 0.07606(9) 0.95472(6) 0.0359(2) Uani 1 1 d . . . . .
F3 F 0.42853(12) 0.00332(7) 0.89089(5) 0.0338(2) Uani 1 1 d . . . . .
F4 F 0.54606(11) 0.48181(8) 0.39746(5) 0.0322(2) Uani 1 1 d . . . . .
F5 F 0.68158(13) 0.65294(8) 0.50622(5) 0.0331(2) Uani 1 1 d . . . . .
F6 F 0.84356(11) 0.53447(7) 0.46038(5) 0.02687(19) 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
C1 N1 1.3124(16) . ?
C1 C2 1.4036(17) . ?
C1 C10 1.5128(17) . ?
C2 C3 1.3805(17) . ?
C3 C4 1.4253(17) . ?
C3 C12 1.4345(17) . ?
C4 C5 1.4165(17) . ?
C4 C9 1.4249(16) . ?
C5 C6 1.3644(19) . ?
C6 C7 1.4106(18) . ?
C7 C8 1.3770(17) . ?
C8 C9 1.4255(17) . ?
C8 C11 1.5012(17) . ?
C9 N1 1.3685(15) . ?
C10 F1 1.3313(15) . ?
C10 F3 1.3320(14) . ?
C10 F2 1.3382(15) . ?
C12 C13 1.1967(18) . ?
C13 C14 1.4387(17) . ?
C14 C16 1.5157(17) . ?
C14 C17 1.5191(18) . ?
C16 C17 1.4923(19) . ?
C18 N2 1.3132(16) . ?
C18 C19 1.4030(17) . ?
C18 C27 1.5133(17) . ?
C19 C20 1.3810(17) . ?
C20 C21 1.4223(17) . ?
C20 C30 1.4366(17) . ?
C21 C22 1.4184(17) . ?
C21 C26 1.4252(16) . ?
C22 C23 1.3654(19) . ?
C23 C24 1.4102(18) . ?
C24 C25 1.3738(18) . ?
C25 C26 1.4252(17) . ?
C25 C29 1.5020(17) . ?
C26 N2 1.3656(15) . ?
C27 F5 1.3334(15) . ?
C27 F4 1.3390(15) . ?
C27 F6 1.3455(14) . ?
C30 C31 1.1976(18) . ?
C31 C32 1.4377(17) . ?
C32 C34 1.5117(17) . ?
C32 C33 1.5158(19) . ?
C33 C34 1.479(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 126.01(11) . . ?
N1 C1 C10 114.05(10) . . ?
C2 C1 C10 119.93(11) . . ?
C3 C2 C1 118.01(11) . . ?
C2 C3 C4 118.51(11) . . ?
C2 C3 C12 120.94(11) . . ?
C4 C3 C12 120.54(11) . . ?
C5 C4 C9 119.34(11) . . ?
C5 C4 C3 122.21(11) . . ?
C9 C4 C3 118.45(11) . . ?
C6 C5 C4 119.76(12) . . ?
C5 C6 C7 120.87(11) . . ?
C8 C7 C6 121.69(12) . . ?
C7 C8 C9 118.22(11) . . ?
C7 C8 C11 121.37(12) . . ?
C9 C8 C11 120.41(11) . . ?
N1 C9 C4 121.85(11) . . ?
N1 C9 C8 118.03(11) . . ?
C4 C9 C8 120.11(11) . . ?
F1 C10 F3 106.74(10) . . ?
F1 C10 F2 106.80(10) . . ?
F3 C10 F2 106.32(10) . . ?
F1 C10 C1 112.44(10) . . ?
F3 C10 C1 112.67(10) . . ?
F2 C10 C1 111.46(10) . . ?
C13 C12 C3 177.66(13) . . ?
C12 C13 C14 177.73(13) . . ?
C13 C14 C16 118.48(11) . . ?
C13 C14 C17 118.21(11) . . ?
C16 C14 C17 58.91(9) . . ?
C17 C16 C14 60.66(8) . . ?
C16 C17 C14 60.43(9) . . ?
N2 C18 C19 126.03(11) . . ?
N2 C18 C27 113.93(11) . . ?
C19 C18 C27 120.04(11) . . ?
C20 C19 C18 117.70(12) . . ?
C19 C20 C21 119.01(11) . . ?
C19 C20 C30 120.83(12) . . ?
C21 C20 C30 120.13(11) . . ?
C22 C21 C20 122.83(11) . . ?
C22 C21 C26 119.21(11) . . ?
C20 C21 C26 117.96(11) . . ?
C23 C22 C21 119.76(12) . . ?
C22 C23 C24 120.85(12) . . ?
C25 C24 C23 121.70(12) . . ?
C24 C25 C26 118.35(11) . . ?
C24 C25 C29 121.71(12) . . ?
C26 C25 C29 119.93(11) . . ?
N2 C26 C25 117.66(11) . . ?
N2 C26 C21 122.23(11) . . ?
C25 C26 C21 120.11(11) . . ?
F5 C27 F4 107.35(10) . . ?
F5 C27 F6 106.87(10) . . ?
F4 C27 F6 106.02(10) . . ?
F5 C27 C18 112.45(10) . . ?
F4 C27 C18 112.21(11) . . ?
F6 C27 C18 111.56(10) . . ?
C31 C30 C20 175.45(14) . . ?
C30 C31 C32 176.38(14) . . ?
C31 C32 C34 118.48(11) . . ?
C31 C32 C33 117.59(11) . . ?
C34 C32 C33 58.49(9) . . ?
C34 C33 C32 60.62(9) . . ?
C33 C34 C32 60.89(9) . . ?
C1 N1 C9 117.16(10) . . ?
C18 N2 C26 117.05(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -0.34(18) . . . . ?
C10 C1 C2 C3 177.84(10) . . . . ?
C1 C2 C3 C4 0.92(17) . . . . ?
C1 C2 C3 C12 -178.65(11) . . . . ?
C2 C3 C4 C5 178.99(11) . . . . ?
C12 C3 C4 C5 -1.44(17) . . . . ?
C2 C3 C4 C9 -0.62(16) . . . . ?
C12 C3 C4 C9 178.95(10) . . . . ?
C9 C4 C5 C6 0.49(18) . . . . ?
C3 C4 C5 C6 -179.12(11) . . . . ?
C4 C5 C6 C7 -0.59(19) . . . . ?
C5 C6 C7 C8 -0.07(19) . . . . ?
C6 C7 C8 C9 0.80(18) . . . . ?
C6 C7 C8 C11 -178.45(11) . . . . ?
C5 C4 C9 N1 -179.93(10) . . . . ?
C3 C4 C9 N1 -0.31(17) . . . . ?
C5 C4 C9 C8 0.26(17) . . . . ?
C3 C4 C9 C8 179.88(10) . . . . ?
C7 C8 C9 N1 179.29(10) . . . . ?
C11 C8 C9 N1 -1.44(16) . . . . ?
C7 C8 C9 C4 -0.89(17) . . . . ?
C11 C8 C9 C4 178.38(10) . . . . ?
N1 C1 C10 F1 -173.60(10) . . . . ?
C2 C1 C10 F1 8.01(16) . . . . ?
N1 C1 C10 F3 -52.92(14) . . . . ?
C2 C1 C10 F3 128.69(12) . . . . ?
N1 C1 C10 F2 66.51(14) . . . . ?
C2 C1 C10 F2 -111.88(12) . . . . ?
C13 C14 C16 C17 -107.51(13) . . . . ?
C13 C14 C17 C16 107.97(13) . . . . ?
N2 C18 C19 C20 1.79(18) . . . . ?
C27 C18 C19 C20 -177.78(11) . . . . ?
C18 C19 C20 C21 -1.31(17) . . . . ?
C18 C19 C20 C30 176.76(11) . . . . ?
C19 C20 C21 C22 179.80(11) . . . . ?
C30 C20 C21 C22 1.72(17) . . . . ?
C19 C20 C21 C26 -0.05(16) . . . . ?
C30 C20 C21 C26 -178.13(10) . . . . ?
C20 C21 C22 C23 179.91(11) . . . . ?
C26 C21 C22 C23 -0.24(17) . . . . ?
C21 C22 C23 C24 -0.27(18) . . . . ?
C22 C23 C24 C25 0.09(19) . . . . ?
C23 C24 C25 C26 0.59(18) . . . . ?
C23 C24 C25 C29 -179.14(11) . . . . ?
C24 C25 C26 N2 178.50(10) . . . . ?
C29 C25 C26 N2 -1.76(17) . . . . ?
C24 C25 C26 C21 -1.10(17) . . . . ?
C29 C25 C26 C21 178.64(10) . . . . ?
C22 C21 C26 N2 -178.65(10) . . . . ?
C20 C21 C26 N2 1.21(17) . . . . ?
C22 C21 C26 C25 0.93(17) . . . . ?
C20 C21 C26 C25 -179.21(10) . . . . ?
N2 C18 C27 F5 -176.74(10) . . . . ?
C19 C18 C27 F5 2.88(17) . . . . ?
N2 C18 C27 F4 -55.60(14) . . . . ?
C19 C18 C27 F4 124.02(12) . . . . ?
N2 C18 C27 F6 63.20(14) . . . . ?
C19 C18 C27 F6 -117.18(12) . . . . ?
C31 C32 C33 C34 -108.10(13) . . . . ?
C31 C32 C34 C33 106.59(14) . . . . ?
C2 C1 N1 C9 -0.58(18) . . . . ?
C10 C1 N1 C9 -178.85(10) . . . . ?
C4 C9 N1 C1 0.89(16) . . . . ?
C8 C9 N1 C1 -179.29(10) . . . . ?
C19 C18 N2 C26 -0.67(18) . . . . ?
C27 C18 N2 C26 178.92(10) . . . . ?
C25 C26 N2 C18 179.55(10) . . . . ?
C21 C26 N2 C18 -0.87(17) . . . . ?

_refine_diff_density_max         0.355
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.055

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform'
####################################################################### 
# 
# 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_4S
_database_code_depnum_ccdc_archive 'CCDC 1585045'
_audit_update_record             
;
2017-11-10 deposited with the CCDC.
2018-03-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H10 F3 N'
_chemical_formula_sum            'C15 H10 F3 N'
_chemical_formula_weight         261.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.2655(4)
_cell_length_b                   17.2610(6)
_cell_length_c                   13.9511(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.431(2)
_cell_angle_gamma                90
_cell_volume                     2471.96(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8692
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      28.19

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.114
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38419
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.877
_diffrn_reflns_theta_max         28.363
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6163
_reflns_number_gt                4006
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT-plus (Bruker, 2008)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2008)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 2012)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0866P)²+1.2157P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6163
_refine_ls_number_parameters     398
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0623
_refine_ls_wR_factor_ref         0.1901
_refine_ls_wR_factor_gt          0.1643
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.33421(14) 0.92524(12) 0.41776(16) 0.0909(7) Uani 1 1 d . . . . .
F2 F 0.34498(16) 0.92667(14) 0.26844(18) 0.1086(9) Uani 1 1 d . . . . .
F3 F 0.32390(14) 0.82058(9) 0.34085(17) 0.0886(7) Uani 1 1 d . . . . .
F4 F 1.15067(16) 0.78110(13) 0.68106(18) 0.0979(7) Uani 1 1 d . . . . .
C8 C 0.79110(19) 1.01540(11) 0.37827(15) 0.0330(4) Uani 1 1 d . . . . .
H8 H 0.7440 1.0627 0.3817 0.040 Uiso 1 1 calc R U . . .
N1 N 0.59043(15) 0.94714(9) 0.35986(13) 0.0323(4) Uani 1 1 d . . . . .
N3 N 0.90030(14) 0.80269(8) 0.59798(11) 0.0271(3) Uani 1 1 d . . . . .
C14 C 0.8714(3) 0.52645(15) 0.3777(3) 0.0702(9) Uani 1 1 d . . . . .
H14A H 0.8160 0.5343 0.4347 0.084 Uiso 1 1 calc R U . . .
H14B H 0.8609 0.4756 0.3458 0.084 Uiso 1 1 calc R U . . .
C13 C 0.8991(3) 0.59532(14) 0.31592(18) 0.0553(7) Uani 1 1 d . . . . .
H13 H 0.9092 0.5832 0.2463 0.066 Uiso 1 1 calc R U . . .
C12 C 0.8395(2) 0.66951(12) 0.33543(15) 0.0406(5) Uani 1 1 d . . . . .
C11 C 0.7885(2) 0.73060(11) 0.34497(14) 0.0344(4) Uani 1 1 d . . . . .
C3 C 0.72331(18) 0.80404(10) 0.35100(13) 0.0280(4) Uani 1 1 d . . . . .
C4 C 0.79442(17) 0.87414(10) 0.36121(13) 0.0263(4) Uani 1 1 d . . . . .
C9 C 0.72338(17) 0.94449(10) 0.36575(13) 0.0276(4) Uani 1 1 d . . . . .
C7 C 0.92394(19) 1.01593(13) 0.38545(15) 0.0375(5) Uani 1 1 d . . . . .
H7 H 0.9689 1.0635 0.3946 0.045 Uiso 1 1 calc R U . . .
C10 C 0.3829(2) 0.88754(13) 0.3431(2) 0.0465(6) Uani 1 1 d . . . . .
C1 C 0.52961(18) 0.88080(11) 0.34979(15) 0.0327(4) Uani 1 1 d . . . . .
C6 C 0.99415(19) 0.94623(13) 0.37934(16) 0.0396(5) Uani 1 1 d . . . . .
H6 H 1.0865 0.9474 0.3834 0.048 Uiso 1 1 calc R U . . .
C5 C 0.93253(18) 0.87713(12) 0.36772(14) 0.0341(4) Uani 1 1 d . . . . .
H5 H 0.9819 0.8307 0.3639 0.041 Uiso 1 1 calc R U . . .
C2 C 0.58936(19) 0.80772(10) 0.34532(14) 0.0311(4) Uani 1 1 d . . . . .
H2 H 0.5387 0.7620 0.3386 0.037 Uiso 1 1 calc R U . . .
C15 C 0.9998(3) 0.56097(15) 0.3786(2) 0.0577(7) Uani 1 1 d . . . . .
H15A H 1.0711 0.5318 0.3477 0.069 Uiso 1 1 calc R U . . .
H15B H 1.0262 0.5905 0.4364 0.069 Uiso 1 1 calc R U . . .
C21 C 0.4962(2) 0.80409(13) 0.59686(17) 0.0424(5) Uani 1 1 d . . . . .
H21 H 0.4037 0.8058 0.5969 0.051 Uiso 1 1 calc R U . . .
C22 C 0.5672(2) 0.87361(12) 0.59247(16) 0.0388(5) Uani 1 1 d . . . . .
H22 H 0.5226 0.9218 0.5896 0.047 Uiso 1 1 calc R U . . .
C23 C 0.70032(18) 0.87213(10) 0.59237(14) 0.0304(4) Uani 1 1 d . . . . .
H23 H 0.7478 0.9193 0.5890 0.036 Uiso 1 1 calc R U . . .
C24 C 0.76749(17) 0.80086(10) 0.59726(13) 0.0243(4) Uani 1 1 d . . . . .
C16 C 0.96120(17) 0.73583(11) 0.60431(14) 0.0291(4) Uani 1 1 d . . . . .
C25 C 1.1078(2) 0.74226(14) 0.60585(19) 0.0470(6) Uani 1 1 d . . . . .
C20 C 0.55808(18) 0.73426(12) 0.60105(16) 0.0357(5) Uani 1 1 d . . . . .
H20 H 0.5085 0.6878 0.6036 0.043 Uiso 1 1 calc R U . . .
C19 C 0.69600(17) 0.73064(10) 0.60162(13) 0.0251(4) Uani 1 1 d . . . . .
C18 C 0.76669(18) 0.65996(10) 0.60768(13) 0.0274(4) Uani 1 1 d . . . . .
C26 C 0.7007(2) 0.58694(12) 0.61068(19) 0.0437(5) Uani 1 1 d . . . . .
C17 C 0.90067(18) 0.66311(10) 0.61006(14) 0.0292(4) Uani 1 1 d . . . . .
H17 H 0.9510 0.6171 0.6155 0.035 Uiso 1 1 calc R U . . .
C26A C 0.5988(5) 0.4473(3) 0.5773(4) 0.0500(16) Uani 0.544(8) 1 d . . P A 1
H26A H 0.5774 0.4347 0.5090 0.060 Uiso 0.544(8) 1 calc R U P A 1
C25A C 0.6578(5) 0.5233(3) 0.5927(5) 0.0346(11) Uani 0.544(8) 1 d . . P A 1
C27A C 0.5092(6) 0.4146(3) 0.6477(6) 0.063(2) Uani 0.544(8) 1 d . . P A 1
H27A H 0.4331 0.3852 0.6232 0.075 Uiso 0.544(8) 1 calc R U P A 1
H27B H 0.4925 0.4452 0.7064 0.075 Uiso 0.544(8) 1 calc R U P A 1
C28A C 0.6380(8) 0.3792(6) 0.6377(11) 0.076(4) Uani 0.544(8) 1 d . . P A 1
H28A H 0.6432 0.3279 0.6063 0.091 Uiso 0.544(8) 1 calc R U P A 1
H28B H 0.7027 0.3879 0.6897 0.091 Uiso 0.544(8) 1 calc R U P A 1
F5A F 1.1544(9) 0.7885(5) 0.5422(9) 0.089(3) Uani 0.544(8) 1 d . . P A 1
F6A F 1.1668(9) 0.6761(5) 0.5985(9) 0.077(3) Uani 0.544(8) 1 d . . P A 1
C26B C 0.5626(7) 0.4601(3) 0.6485(6) 0.069(2) Uani 0.456(8) 1 d . . P A 2
H26B H 0.4775 0.4678 0.6817 0.083 Uiso 0.456(8) 1 calc R U P A 2
C25B C 0.6355(7) 0.5308(4) 0.6347(5) 0.0406(15) Uani 0.456(8) 1 d . . P A 2
C27B C 0.5620(11) 0.3967(4) 0.5807(5) 0.070(3) Uani 0.456(8) 1 d . . P A 2
H27C H 0.4787 0.3692 0.5693 0.084 Uiso 0.456(8) 1 calc R U P A 2
H27D H 0.6187 0.4011 0.5238 0.084 Uiso 0.456(8) 1 calc R U P A 2
C28B C 0.6190(19) 0.3884(8) 0.6654(15) 0.128(9) Uani 0.456(8) 1 d . . P A 2
H28C H 0.7153 0.3860 0.6670 0.154 Uiso 0.456(8) 1 calc R U P A 2
H28D H 0.5758 0.3541 0.7124 0.154 Uiso 0.456(8) 1 calc R U P A 2
F6B F 1.1651(12) 0.6755(8) 0.6211(12) 0.099(4) Uani 0.456(8) 1 d . . P A 2
F5B F 1.1492(12) 0.7692(8) 0.5229(10) 0.112(5) Uani 0.456(8) 1 d . . P A 2


_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 C10 1.329(3) . ?
F2 C10 1.299(3) . ?
F3 C10 1.305(3) . ?
F4 C25 1.318(3) . ?
C8 C7 1.367(3) . ?
C8 C9 1.418(3) . ?
N1 C1 1.311(2) . ?
N1 C9 1.367(2) . ?
N3 C16 1.315(2) . ?
N3 C24 1.364(2) . ?
C14 C15 1.446(4) . ?
C14 C13 1.497(4) . ?
C13 C12 1.446(3) . ?
C13 C15 1.474(3) . ?
C12 C11 1.186(3) . ?
C11 C3 1.436(2) . ?
C3 C2 1.378(3) . ?
C3 C4 1.420(3) . ?
C4 C9 1.418(2) . ?
C4 C5 1.421(3) . ?
C7 C6 1.405(3) . ?
C10 C1 1.512(3) . ?
C1 C2 1.404(3) . ?
C6 C5 1.359(3) . ?
C21 C20 1.363(3) . ?
C21 C22 1.406(3) . ?
C22 C23 1.366(3) . ?
C23 C24 1.412(2) . ?
C24 C19 1.418(2) . ?
C16 C17 1.403(3) . ?
C16 C25 1.509(3) . ?
C25 F5A 1.288(8) . ?
C25 F6A 1.297(7) . ?
C25 F6B 1.311(11) . ?
C25 F5B 1.321(11) . ?
C20 C19 1.417(2) . ?
C19 C18 1.422(2) . ?
C18 C17 1.377(2) . ?
C18 C26 1.432(3) . ?
C26 C25A 1.210(5) . ?
C26 C25B 1.226(7) . ?
C26A C25A 1.460(7) . ?
C26A C27A 1.463(8) . ?
C26A C28A 1.500(13) . ?
C27A C28A 1.465(10) . ?
C26B C28B 1.385(16) . ?
C26B C25B 1.446(8) . ?
C26B C27B 1.447(10) . ?
C27B C28B 1.323(19) . ?

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
C7 C8 C9 120.20(18) . . ?
C1 N1 C9 116.84(15) . . ?
C16 N3 C24 117.06(15) . . ?
C15 C14 C13 60.08(19) . . ?
C12 C13 C15 122.7(2) . . ?
C12 C13 C14 120.9(2) . . ?
C15 C13 C14 58.24(18) . . ?
C11 C12 C13 175.5(2) . . ?
C12 C11 C3 176.6(2) . . ?
C2 C3 C4 118.58(16) . . ?
C2 C3 C11 120.15(18) . . ?
C4 C3 C11 121.26(17) . . ?
C9 C4 C3 118.04(16) . . ?
C9 C4 C5 118.64(17) . . ?
C3 C4 C5 123.32(16) . . ?
N1 C9 C8 117.83(16) . . ?
N1 C9 C4 122.64(16) . . ?
C8 C9 C4 119.52(17) . . ?
C8 C7 C6 120.11(19) . . ?
F2 C10 F3 107.7(2) . . ?
F2 C10 F1 105.1(2) . . ?
F3 C10 F1 106.0(2) . . ?
F2 C10 C1 112.5(2) . . ?
F3 C10 C1 113.28(18) . . ?
F1 C10 C1 111.70(19) . . ?
N1 C1 C2 125.55(17) . . ?
N1 C1 C10 114.36(16) . . ?
C2 C1 C10 120.09(17) . . ?
C5 C6 C7 121.33(18) . . ?
C6 C5 C4 120.18(18) . . ?
C3 C2 C1 118.35(17) . . ?
C14 C15 C13 61.7(2) . . ?
C20 C21 C22 120.99(19) . . ?
C23 C22 C21 120.20(18) . . ?
C22 C23 C24 120.28(17) . . ?
N3 C24 C23 117.92(16) . . ?
N3 C24 C19 122.48(16) . . ?
C23 C24 C19 119.61(16) . . ?
N3 C16 C17 125.33(17) . . ?
N3 C16 C25 114.20(17) . . ?
C17 C16 C25 120.47(17) . . ?
F5A C25 F6A 108.4(7) . . ?
F5A C25 F4 96.3(6) . . ?
F6A C25 F4 110.9(6) . . ?
F6B C25 F4 99.8(7) . . ?
F6B C25 F5B 107.8(9) . . ?
F4 C25 F5B 114.3(7) . . ?
F5A C25 C16 114.2(5) . . ?
F6A C25 C16 113.6(5) . . ?
F6B C25 C16 112.6(7) . . ?
F4 C25 C16 112.1(2) . . ?
F5B C25 C16 109.9(6) . . ?
C21 C20 C19 120.28(18) . . ?
C20 C19 C24 118.64(16) . . ?
C20 C19 C18 123.20(16) . . ?
C24 C19 C18 118.16(16) . . ?
C17 C18 C19 118.48(16) . . ?
C17 C18 C26 120.46(17) . . ?
C19 C18 C26 121.06(17) . . ?
C25A C26 C18 164.9(4) . . ?
C25B C26 C18 164.5(4) . . ?
C18 C17 C16 118.48(16) . . ?
C25A C26A C27A 120.7(5) . . ?
C25A C26A C28A 120.8(6) . . ?
C27A C26A C28A 59.2(5) . . ?
C26 C25A C26A 175.4(6) . . ?
C26A C27A C28A 61.6(6) . . ?
C27A C28A C26A 59.1(5) . . ?
C28B C26B C25B 124.1(10) . . ?
C28B C26B C27B 55.7(8) . . ?
C25B C26B C27B 123.4(6) . . ?
C26 C25B C26B 171.2(7) . . ?
C28B C27B C26B 59.8(9) . . ?
C27B C28B C26B 64.5(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
C15 C14 C13 C12 -111.7(3) . . . . ?
C2 C3 C4 C9 0.5(3) . . . . ?
C11 C3 C4 C9 179.40(17) . . . . ?
C2 C3 C4 C5 -179.99(18) . . . . ?
C11 C3 C4 C5 -1.1(3) . . . . ?
C1 N1 C9 C8 -178.97(18) . . . . ?
C1 N1 C9 C4 0.1(3) . . . . ?
C7 C8 C9 N1 179.41(18) . . . . ?
C7 C8 C9 C4 0.3(3) . . . . ?
C3 C4 C9 N1 -0.6(3) . . . . ?
C5 C4 C9 N1 179.84(17) . . . . ?
C3 C4 C9 C8 178.48(17) . . . . ?
C5 C4 C9 C8 -1.1(3) . . . . ?
C9 C8 C7 C6 0.7(3) . . . . ?
C9 N1 C1 C2 0.5(3) . . . . ?
C9 N1 C1 C10 -179.65(18) . . . . ?
F2 C10 C1 N1 62.7(3) . . . . ?
F3 C10 C1 N1 -174.8(2) . . . . ?
F1 C10 C1 N1 -55.3(3) . . . . ?
F2 C10 C1 C2 -117.4(2) . . . . ?
F3 C10 C1 C2 5.0(3) . . . . ?
F1 C10 C1 C2 124.6(2) . . . . ?
C8 C7 C6 C5 -1.0(3) . . . . ?
C7 C6 C5 C4 0.2(3) . . . . ?
C9 C4 C5 C6 0.9(3) . . . . ?
C3 C4 C5 C6 -178.68(19) . . . . ?
C4 C3 C2 C1 0.1(3) . . . . ?
C11 C3 C2 C1 -178.86(18) . . . . ?
N1 C1 C2 C3 -0.6(3) . . . . ?
C10 C1 C2 C3 179.56(19) . . . . ?
C12 C13 C15 C14 108.6(3) . . . . ?
C20 C21 C22 C23 0.0(4) . . . . ?
C21 C22 C23 C24 -0.4(3) . . . . ?
C16 N3 C24 C23 178.80(17) . . . . ?
C16 N3 C24 C19 -0.9(3) . . . . ?
C22 C23 C24 N3 -179.30(18) . . . . ?
C22 C23 C24 C19 0.4(3) . . . . ?
C24 N3 C16 C17 0.2(3) . . . . ?
C24 N3 C16 C25 -179.34(18) . . . . ?
N3 C16 C25 F5A -45.8(6) . . . . ?
C17 C16 C25 F5A 134.7(6) . . . . ?
N3 C16 C25 F6A -170.9(6) . . . . ?
C17 C16 C25 F6A 9.6(7) . . . . ?
N3 C16 C25 F6B 174.0(8) . . . . ?
C17 C16 C25 F6B -5.5(8) . . . . ?
N3 C16 C25 F4 62.4(3) . . . . ?
C17 C16 C25 F4 -117.1(2) . . . . ?
N3 C16 C25 F5B -65.8(8) . . . . ?
C17 C16 C25 F5B 114.7(7) . . . . ?
C22 C21 C20 C19 0.4(3) . . . . ?
C21 C20 C19 C24 -0.3(3) . . . . ?
C21 C20 C19 C18 178.8(2) . . . . ?
N3 C24 C19 C20 179.64(17) . . . . ?
C23 C24 C19 C20 -0.1(3) . . . . ?
N3 C24 C19 C18 0.5(3) . . . . ?
C23 C24 C19 C18 -179.23(17) . . . . ?
C20 C19 C18 C17 -178.43(18) . . . . ?
C24 C19 C18 C17 0.7(3) . . . . ?
C20 C19 C18 C26 2.0(3) . . . . ?
C24 C19 C18 C26 -178.94(19) . . . . ?
C17 C18 C26 C25A -67.5(12) . . . . ?
C19 C18 C26 C25A 112.1(12) . . . . ?
C17 C18 C26 C25B 111.4(15) . . . . ?
C19 C18 C26 C25B -69.0(15) . . . . ?
C19 C18 C17 C16 -1.3(3) . . . . ?
C26 C18 C17 C16 178.28(19) . . . . ?
N3 C16 C17 C18 1.0(3) . . . . ?
C25 C16 C17 C18 -179.53(19) . . . . ?
C25A C26A C27A C28A -109.9(8) . . . . ?
C25A C26A C28A C27A 109.6(7) . . . . ?
C25B C26B C27B C28B 111.2(13) . . . . ?
C25B C26B C28B C27B -110.1(10) . . . . ?

_refine_diff_density_max         0.531
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.056

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform'
####################################################################### 
# 
# 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_4K
_database_code_depnum_ccdc_archive 'CCDC 1585040'
_audit_update_record             
;
2017-11-10 deposited with the CCDC.
2018-03-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14 F3 N'
_chemical_formula_sum            'C20 H14 F3 N'
_chemical_formula_weight         325.32

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0038(2)
_cell_length_b                   9.5959(4)
_cell_length_c                   10.82930(10)
_cell_angle_alpha                71.6650(10)
_cell_angle_beta                 75.536(3)
_cell_angle_gamma                63.700(2)
_cell_volume                     789.48(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9944
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      25.29
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25836
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.998
_diffrn_reflns_theta_max         25.352
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2882
_reflns_number_gt                2394
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT-plus (Bruker, 2008)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2008)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0469P)²+0.3119P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2882
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0993
_refine_ls_wR_factor_gt          0.0922
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C17 C 0.26863(17) 1.11454(17) 0.42853(13) 0.0266(3) Uani 1 1 d . . . . .
C16 C 0.24418(18) 0.98837(17) 0.41231(14) 0.0284(3) Uani 1 1 d . . . . .
H16 H 0.155745 0.960535 0.465928 0.034 Uiso 1 1 calc R U . . .
C15 C 0.34584(18) 0.90260(17) 0.31982(14) 0.0272(3) Uani 1 1 d . . . . .
H15 H 0.327390 0.816100 0.311360 0.033 Uiso 1 1 calc R U . . .
C14 C 0.47526(17) 0.94226(16) 0.23888(13) 0.0224(3) Uani 1 1 d . . . . .
C19 C 0.49962(17) 1.06984(16) 0.25391(14) 0.0257(3) Uani 1 1 d . . . . .
H19 H 0.586392 1.099531 0.199194 0.031 Uiso 1 1 calc R U . . .
C18 C 0.39798(18) 1.15303(17) 0.34807(14) 0.0275(3) Uani 1 1 d . . . . .
H18 H 0.417191 1.238449 0.357847 0.033 Uiso 1 1 calc R U . . .
C13 C 0.58018(17) 0.85424(16) 0.14251(14) 0.0238(3) Uani 1 1 d . . . . .
C12 C 0.66718(17) 0.77684(16) 0.06376(13) 0.0235(3) Uani 1 1 d . . . . .
C3 C 0.76846(16) 0.68533(15) -0.03078(13) 0.0218(3) Uani 1 1 d . . . . .
C2 C 0.73229(17) 0.56747(16) -0.04712(13) 0.0232(3) Uani 1 1 d . . . . .
H2 H 0.641385 0.543209 0.005693 0.028 Uiso 1 1 calc R U . . .
C1 C 0.83306(17) 0.48434(16) -0.14364(13) 0.0235(3) Uani 1 1 d . . . . .
C9 C 1.00467(17) 0.61903(15) -0.20296(13) 0.0224(3) Uani 1 1 d . . . . .
C4 C 0.90883(17) 0.71437(15) -0.11068(13) 0.0223(3) Uani 1 1 d . . . . .
C5 C 0.95470(18) 0.83295(16) -0.10044(14) 0.0270(3) Uani 1 1 d . . . . .
H5 H 0.889650 0.898831 -0.040613 0.032 Uiso 1 1 calc R U . . .
C6 C 1.09227(19) 0.85234(17) -0.17656(15) 0.0316(3) Uani 1 1 d . . . . .
H6 H 1.122980 0.932098 -0.169561 0.038 Uiso 1 1 calc R U . . .
C7 C 1.18988(18) 0.75557(18) -0.26571(15) 0.0310(3) Uani 1 1 d . . . . .
H7 H 1.286762 0.770253 -0.316301 0.037 Uiso 1 1 calc R U . . .
C8 C 1.14954(17) 0.64065(16) -0.28187(14) 0.0267(3) Uani 1 1 d . . . . .
C11 C 1.25380(19) 0.53928(19) -0.37832(15) 0.0332(4) Uani 1 1 d . . . . .
H11A H 1.346943 0.570611 -0.423835 0.050 Uiso 1 1 calc R U . . .
H11B H 1.184756 0.554669 -0.442458 0.050 Uiso 1 1 calc R U . . .
H11C H 1.297673 0.426470 -0.331575 0.050 Uiso 1 1 calc R U . . .
C10 C 0.78977(19) 0.36361(17) -0.17166(14) 0.0300(3) Uani 1 1 d . . . . .
C20 C 0.1580(2) 1.2072(2) 0.52986(15) 0.0371(4) Uani 1 1 d . . . . .
H20A H 0.074203 1.163486 0.577139 0.056 Uiso 1 1 calc R U . . .
H20B H 0.226095 1.198570 0.591957 0.056 Uiso 1 1 calc R U . . .
H20C H 0.101859 1.319878 0.486385 0.056 Uiso 1 1 calc R U . . .
N1 N 0.96396(14) 0.50578(13) -0.21967(11) 0.0235(3) Uani 1 1 d . . . . .
F2 F 0.92127(12) 0.22898(11) -0.18402(10) 0.0432(3) Uani 1 1 d . . . . .
F3 F 0.67938(12) 0.32110(11) -0.07779(10) 0.0435(3) Uani 1 1 d . . . . .
F4 F 0.72328(17) 0.42145(13) -0.28385(11) 0.0608(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
C17 C18 1.387(2) . ?
C17 C16 1.391(2) . ?
C17 C20 1.5066(19) . ?
C16 C15 1.383(2) . ?
C16 H16 0.9500 . ?
C15 C14 1.394(2) . ?
C15 H15 0.9500 . ?
C14 C19 1.3980(19) . ?
C14 C13 1.4318(19) . ?
C19 C18 1.383(2) . ?
C19 H19 0.9500 . ?
C18 H18 0.9500 . ?
C13 C12 1.2007(19) . ?
C12 C3 1.4285(18) . ?
C3 C2 1.3775(19) . ?
C3 C4 1.4275(19) . ?
C2 C1 1.4005(19) . ?
C2 H2 0.9500 . ?
C1 N1 1.3164(18) . ?
C1 C10 1.5054(19) . ?
C9 N1 1.3630(18) . ?
C9 C4 1.4230(19) . ?
C9 C8 1.430(2) . ?
C4 C5 1.4129(19) . ?
C5 C6 1.359(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.408(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.374(2) . ?
C7 H7 0.9500 . ?
C8 C11 1.503(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C10 F2 1.3278(17) . ?
C10 F3 1.3347(17) . ?
C10 F4 1.3369(18) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 C17 C16 117.91(13) . . ?
C18 C17 C20 120.86(14) . . ?
C16 C17 C20 121.23(14) . . ?
C15 C16 C17 121.41(13) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C16 C15 C14 120.41(13) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C14 C19 118.47(12) . . ?
C15 C14 C13 120.55(12) . . ?
C19 C14 C13 120.98(13) . . ?
C18 C19 C14 120.31(13) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
C19 C18 C17 121.48(13) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C12 C13 C14 178.18(15) . . ?
C13 C12 C3 179.12(14) . . ?
C2 C3 C4 118.57(12) . . ?
C2 C3 C12 120.65(12) . . ?
C4 C3 C12 120.78(12) . . ?
C3 C2 C1 118.25(12) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
N1 C1 C2 125.73(13) . . ?
N1 C1 C10 114.35(12) . . ?
C2 C1 C10 119.86(12) . . ?
N1 C9 C4 122.36(12) . . ?
N1 C9 C8 117.85(12) . . ?
C4 C9 C8 119.79(12) . . ?
C5 C4 C9 119.71(12) . . ?
C5 C4 C3 122.28(12) . . ?
C9 C4 C3 118.01(12) . . ?
C6 C5 C4 119.70(13) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C7 120.78(14) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C6 122.13(13) . . ?
C8 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C7 C8 C9 117.86(13) . . ?
C7 C8 C11 121.61(13) . . ?
C9 C8 C11 120.53(13) . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
F2 C10 F3 106.15(12) . . ?
F2 C10 F4 106.30(12) . . ?
F3 C10 F4 106.93(13) . . ?
F2 C10 C1 113.18(12) . . ?
F3 C10 C1 112.75(12) . . ?
F4 C10 C1 111.08(12) . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1 N1 C9 117.04(11) . . ?

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
C18 C17 C16 C15 0.5(2) . . . . ?
C20 C17 C16 C15 -179.72(13) . . . . ?
C17 C16 C15 C14 -0.7(2) . . . . ?
C16 C15 C14 C19 0.2(2) . . . . ?
C16 C15 C14 C13 -179.65(13) . . . . ?
C15 C14 C19 C18 0.6(2) . . . . ?
C13 C14 C19 C18 -179.55(13) . . . . ?
C14 C19 C18 C17 -0.9(2) . . . . ?
C16 C17 C18 C19 0.3(2) . . . . ?
C20 C17 C18 C19 -179.46(13) . . . . ?
C4 C3 C2 C1 -1.44(19) . . . . ?
C12 C3 C2 C1 178.32(12) . . . . ?
C3 C2 C1 N1 1.7(2) . . . . ?
C3 C2 C1 C10 -175.30(12) . . . . ?
N1 C9 C4 C5 -178.24(12) . . . . ?
C8 C9 C4 C5 1.86(19) . . . . ?
N1 C9 C4 C3 1.97(19) . . . . ?
C8 C9 C4 C3 -177.94(12) . . . . ?
C2 C3 C4 C5 179.95(12) . . . . ?
C12 C3 C4 C5 0.2(2) . . . . ?
C2 C3 C4 C9 -0.26(18) . . . . ?
C12 C3 C4 C9 179.98(12) . . . . ?
C9 C4 C5 C6 -1.6(2) . . . . ?
C3 C4 C5 C6 178.20(13) . . . . ?
C4 C5 C6 C7 0.0(2) . . . . ?
C5 C6 C7 C8 1.3(2) . . . . ?
C6 C7 C8 C9 -1.0(2) . . . . ?
C6 C7 C8 C11 179.38(13) . . . . ?
N1 C9 C8 C7 179.54(12) . . . . ?
C4 C9 C8 C7 -0.6(2) . . . . ?
N1 C9 C8 C11 -0.87(19) . . . . ?
C4 C9 C8 C11 179.04(12) . . . . ?
N1 C1 C10 F2 46.92(17) . . . . ?
C2 C1 C10 F2 -135.72(13) . . . . ?
N1 C1 C10 F3 167.43(12) . . . . ?
C2 C1 C10 F3 -15.22(19) . . . . ?
N1 C1 C10 F4 -72.57(16) . . . . ?
C2 C1 C10 F4 104.79(15) . . . . ?
C2 C1 N1 C9 -0.1(2) . . . . ?
C10 C1 N1 C9 177.08(11) . . . . ?
C4 C9 N1 C1 -1.79(19) . . . . ?
C8 C9 N1 C1 178.12(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 F3 0.95 2.61 3.4066(16) 141.3 2_665

_refine_diff_density_max         0.254
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.037

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform'
####################################################################### 
# 
# 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_4L
_database_code_depnum_ccdc_archive 'CCDC 1585041'
_audit_update_record             
;
2017-11-10 deposited with the CCDC.
2018-03-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H20 F3 N'
_chemical_formula_sum            'C23 H20 F3 N'
_chemical_formula_weight         367.40

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.7741(5)
_cell_length_b                   16.4781(7)
_cell_length_c                   22.9605(10)
_cell_angle_alpha                109.808(2)
_cell_angle_beta                 90.168(2)
_cell_angle_gamma                90.052(2)
_cell_volume                     3835.1(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9930
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      28.56

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_F_000             1536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            59847
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.313
_diffrn_reflns_theta_max         29.136
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             18490
_reflns_number_gt                14779
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT-plus (Bruker, 2008)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2008)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0639P)²+2.1551P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         18490
_refine_ls_number_parameters     1033
_refine_ls_number_restraints     63
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1443
_refine_ls_wR_factor_gt          0.1317
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.152
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C11 C -0.0462(3) -0.12556(15) 0.21709(13) 0.0385(6) Uani 1 1 d . . . . .
H11A H -0.117732 -0.151603 0.190987 0.058 Uiso 1 1 calc R U . . .
H11B H -0.050762 -0.137657 0.255976 0.058 Uiso 1 1 calc R U . . .
H11C H 0.030569 -0.149931 0.195384 0.058 Uiso 1 1 calc R U . . .
F11A F 0.5498(4) 0.5978(2) 0.12515(18) 0.0788(10) Uani 0.715(4) 1 d . U P A 1
F10A F 0.7201(3) 0.5301(2) 0.10391(16) 0.0652(8) Uani 0.715(4) 1 d . U P A 1
F12A F 0.5640(4) 0.4841(2) 0.04796(12) 0.0793(12) Uani 0.715(4) 1 d . . P A 1
F7A F 0.0769(5) -0.12378(16) -0.01511(14) 0.0907(16) Uani 0.715(4) 1 d . . P A
1
F9A F 0.1803(3) -0.20268(18) 0.01899(15) 0.0752(10) Uani 0.715(4) 1 d . U P A 1
F8A F 0.0032(4) -0.1704(3) 0.05289(17) 0.0920(11) Uani 0.715(4) 1 d . U P A 1
F11B F 0.6924(6) 0.5785(5) 0.1343(3) 0.0582(19) Uani 0.285(4) 1 d D U P A 2
F12B F 0.5142(5) 0.5649(5) 0.0959(3) 0.0484(17) Uani 0.285(4) 1 d D U P A 2
F10B F 0.6532(9) 0.4749(5) 0.0531(4) 0.093(3) Uani 0.285(4) 1 d D U P A 2
F7B F 0.1638(8) -0.1583(5) -0.0123(4) 0.070(2) Uani 0.285(4) 1 d . U P A 2
F9B F 0.0939(7) -0.2078(4) 0.0520(3) 0.0459(16) Uani 0.285(4) 1 d . U P A 2
F8B F -0.0170(6) -0.1294(4) 0.0260(3) 0.0500(17) Uani 0.285(4) 1 d . U P A 2
C27 C 0.74095(19) 0.40648(13) 0.32993(10) 0.0205(4) Uani 1 1 d . . . . .
C50 C 0.23648(19) 0.07912(13) 0.18188(10) 0.0212(4) Uani 1 1 d . . . . .
C33 C 0.74993(19) 0.49268(12) 0.32995(9) 0.0195(4) Uani 1 1 d . . . . .
C55 C 0.2499(2) -0.00741(13) 0.18098(10) 0.0214(4) Uani 1 1 d . . . . .
C12 C 0.0798(2) 0.26229(14) 0.36707(10) 0.0268(5) Uani 1 1 d . . . . .
C32 C 0.7983(2) 0.50842(13) 0.27685(10) 0.0220(4) Uani 1 1 d . . . . .
C53 C 0.3553(2) 0.04563(15) 0.27950(11) 0.0271(5) Uani 1 1 d . . . . .
H53 H 0.396917 0.035453 0.312900 0.032 Uiso 1 1 calc R U . . .
C25 C 0.6540(2) 0.46425(14) 0.43239(10) 0.0236(4) Uani 1 1 d . . . . .
H25 H 0.620791 0.457891 0.468903 0.028 Uiso 1 1 calc R U . . .
C13 C 0.0870(2) 0.33809(14) 0.37720(10) 0.0260(5) Uani 1 1 d . . . . .
C31 C 0.8383(2) 0.43960(14) 0.22810(10) 0.0250(4) Uani 1 1 d . . . . .
H31 H 0.872349 0.449558 0.193004 0.030 Uiso 1 1 calc R U . . .
C49 C 0.1736(2) 0.09248(13) 0.13107(10) 0.0229(4) Uani 1 1 d . . . . .
C64 C 0.1180(2) 0.50657(13) 0.12847(10) 0.0230(4) Uani 1 1 d . . . . .
C24 C 0.6686(2) 0.54631(13) 0.42736(10) 0.0222(4) Uani 1 1 d . . . . .
C39 C 0.6399(2) 0.14493(14) 0.37497(11) 0.0259(5) Uani 1 1 d . . . . .
C54 C 0.3088(2) -0.02327(14) 0.23186(11) 0.0248(4) Uani 1 1 d . . . . .
C59 C 0.1352(2) 0.25120(14) 0.13396(10) 0.0245(4) Uani 1 1 d . . . . .
C17 C 0.1073(2) 0.60812(13) 0.40821(10) 0.0218(4) Uani 1 1 d . . . . .
C51 C 0.2834(2) 0.14777(13) 0.23287(10) 0.0233(4) Uani 1 1 d . . . . .
H51 H 0.273639 0.205694 0.234274 0.028 Uiso 1 1 calc R U . . .
C47 C 0.1513(2) -0.06009(13) 0.08725(10) 0.0249(5) Uani 1 1 d . . . . .
C4 C 0.0136(2) 0.11726(14) 0.29817(11) 0.0253(4) Uani 1 1 d . . . . .
C58 C 0.1521(2) 0.17855(13) 0.13169(10) 0.0251(5) Uani 1 1 d . . . . .
C9 C 0.0101(2) 0.02663(14) 0.28671(11) 0.0271(5) Uani 1 1 d . . . . .
C66 C 0.1874(2) 0.40487(13) 0.17737(10) 0.0246(4) Uani 1 1 d . . . . .
H66 H 0.233346 0.393694 0.209214 0.030 Uiso 1 1 calc R U . . .
C19 C 0.1168(2) 0.48804(14) 0.44719(10) 0.0257(5) Uani 1 1 d . . . . .
H19 H 0.127549 0.467870 0.481032 0.031 Uiso 1 1 calc R U . . .
C38 C 0.6530(2) 0.23432(14) 0.38045(10) 0.0259(5) Uani 1 1 d . . . . .
C36 C 0.8018(2) 0.59860(14) 0.27502(11) 0.0264(5) Uani 1 1 d . . . . .
H36A H 0.860200 0.601356 0.243115 0.040 Uiso 1 1 calc R U . . .
H36B H 0.828565 0.638490 0.315407 0.040 Uiso 1 1 calc R U . . .
H36C H 0.718737 0.614816 0.265341 0.040 Uiso 1 1 calc R U . . .
C60 C 0.1232(2) 0.33831(13) 0.13404(10) 0.0218(4) Uani 1 1 d . . . . .
C42 C 0.6304(2) -0.03014(14) 0.36583(12) 0.0303(5) Uani 1 1 d . . . . .
C28 C 0.7812(2) 0.33791(13) 0.27801(10) 0.0238(4) Uani 1 1 d . . . . .
H28 H 0.774044 0.280217 0.277521 0.029 Uiso 1 1 calc R U . . .
C48 C 0.1318(2) 0.02192(13) 0.08301(10) 0.0253(5) Uani 1 1 d . . . . .
H48 H 0.091036 0.028569 0.048155 0.030 Uiso 1 1 calc R U . . .
C15 C 0.0809(2) 0.46021(13) 0.33894(10) 0.0246(4) Uani 1 1 d . . . . .
H15 H 0.066864 0.420945 0.298281 0.030 Uiso 1 1 calc R U . . .
C26 C 0.6888(2) 0.39324(13) 0.38314(10) 0.0219(4) Uani 1 1 d . . . . .
C29 C 0.8304(2) 0.35400(14) 0.22830(11) 0.0261(5) Uani 1 1 d . . . . .
H29 H 0.859435 0.307604 0.193748 0.031 Uiso 1 1 calc R U . . .
C57 C 0.3168(2) -0.11333(15) 0.23345(13) 0.0337(5) Uani 1 1 d . . . . .
H57A H 0.369910 -0.113783 0.268072 0.051 Uiso 1 1 calc R U . . .
H57B H 0.352238 -0.151382 0.194517 0.051 Uiso 1 1 calc R U . . .
H57C H 0.233567 -0.133696 0.238802 0.051 Uiso 1 1 calc R U . . .
C16 C 0.0873(2) 0.54809(14) 0.34909(10) 0.0238(4) Uani 1 1 d . . . . .
H16 H 0.077827 0.567942 0.315020 0.029 Uiso 1 1 calc R U . . .
C52 C 0.3427(2) 0.13065(14) 0.27999(11) 0.0262(5) Uani 1 1 d . . . . .
H52 H 0.375994 0.176864 0.313559 0.031 Uiso 1 1 calc R U . . .
C40A C 0.6858(2) 0.08069(15) 0.32345(12) 0.0334(5) Uani 1 1 d . . . . .
H40A H 0.720896 0.095686 0.290568 0.040 Uiso 1 1 calc R U . . .
C37 C 0.6702(2) 0.30717(14) 0.38356(10) 0.0246(4) Uani 1 1 d . . . . .
C65 C 0.1850(2) 0.48781(13) 0.17448(10) 0.0257(5) Uani 1 1 d . . . . .
H65 H 0.229790 0.532565 0.204394 0.031 Uiso 1 1 calc R U . . .
C40 C 0.5841(2) 0.12083(14) 0.42126(11) 0.0305(5) Uani 1 1 d . . . . .
H40 H 0.548653 0.163337 0.456242 0.037 Uiso 1 1 calc R U . . .
C14 C 0.0949(2) 0.42925(13) 0.38798(10) 0.0239(4) Uani 1 1 d . . . . .
C18 C 0.1228(2) 0.57559(14) 0.45691(10) 0.0256(5) Uani 1 1 d . . . . .
H18 H 0.137760 0.614617 0.497543 0.031 Uiso 1 1 calc R U . . .
C62 C 0.0500(2) 0.43932(13) 0.08653(10) 0.0255(5) Uani 1 1 d . . . . .
H62 H 0.001362 0.450792 0.055628 0.031 Uiso 1 1 calc R U . . .
C20 C 0.1042(2) 0.70577(13) 0.42163(10) 0.0251(4) Uani 1 1 d . . . . .
C61 C 0.0519(2) 0.35648(14) 0.08904(10) 0.0267(5) Uani 1 1 d . . . . .
H61 H 0.004745 0.312028 0.060160 0.032 Uiso 1 1 calc R U . . .
C34 C 0.6238(2) 0.62513(14) 0.47895(11) 0.0286(5) Uani 1 1 d . . . . .
C3 C 0.0717(2) 0.17087(13) 0.35371(10) 0.0254(5) Uani 1 1 d . . . . .
C5 C -0.0387(2) 0.15030(15) 0.25403(11) 0.0293(5) Uani 1 1 d . . . . .
H5 H -0.034918 0.210390 0.260735 0.035 Uiso 1 1 calc R U . . .
C43 C 0.6811(2) -0.00473(15) 0.31928(14) 0.0380(6) Uani 1 1 d . . . . .
H43 H 0.713488 -0.047396 0.283472 0.046 Uiso 1 1 calc R U . . .
C7 C -0.0985(2) 0.00660(16) 0.19086(12) 0.0348(6) Uani 1 1 d . . . . .
H7 H -0.138322 -0.029897 0.154424 0.042 Uiso 1 1 calc R U . . .
C1 C 0.1144(2) 0.04299(14) 0.37707(11) 0.0308(5) Uani 1 1 d . . . . .
C2 C 0.1233(2) 0.13321(14) 0.39313(11) 0.0289(5) Uani 1 1 d . . . . .
H2 H 0.163823 0.167149 0.430205 0.035 Uiso 1 1 calc R U . . .
C56 C 0.1024(2) -0.13874(15) 0.03639(11) 0.0320(5) Uani 1 1 d . . . . .
C8 C -0.0470(2) -0.02950(15) 0.23079(11) 0.0306(5) Uani 1 1 d . . . . .
C41 C 0.5804(2) 0.03401(15) 0.41611(12) 0.0332(5) Uani 1 1 d . . . . .
H41 H 0.542375 0.018423 0.448093 0.040 Uiso 1 1 calc R U . . .
C67 C 0.1233(2) 0.59519(14) 0.12013(12) 0.0291(5) Uani 1 1 d . . . . .
C22 C 0.1041(2) 0.72885(14) 0.36243(11) 0.0298(5) Uani 1 1 d . . . . .
H22A H 0.180735 0.707896 0.339373 0.045 Uiso 1 1 calc R U . . .
H22B H 0.032453 0.701813 0.336764 0.045 Uiso 1 1 calc R U . . .
H22C H 0.099077 0.791615 0.373244 0.045 Uiso 1 1 calc R U . . .
C6 C -0.0944(2) 0.09567(16) 0.20179(12) 0.0332(5) Uani 1 1 d . . . . .
H6 H -0.130709 0.118212 0.172730 0.040 Uiso 1 1 calc R U . . .
C21 C 0.2157(3) 0.75042(14) 0.46164(12) 0.0352(6) Uani 1 1 d . . . . .
H21A H 0.292752 0.729009 0.439151 0.053 Uiso 1 1 calc R U . . .
H21B H 0.209885 0.812874 0.470861 0.053 Uiso 1 1 calc R U . . .
H21C H 0.215455 0.737832 0.500403 0.053 Uiso 1 1 calc R U . . .
C23 C -0.0163(3) 0.73915(16) 0.45669(13) 0.0366(6) Uani 1 1 d . . . . .
H23A H -0.017728 0.724883 0.494798 0.055 Uiso 1 1 calc R U . . .
H23B H -0.020769 0.801870 0.467110 0.055 Uiso 1 1 calc R U . . .
H23C H -0.087393 0.712068 0.430629 0.055 Uiso 1 1 calc R U . . .
C43A C 0.6388(3) -0.12484(15) 0.36256(15) 0.0404(6) Uani 1 1 d . . . . .
C70 C -0.0076(3) 0.62685(16) 0.11214(14) 0.0409(6) Uani 1 1 d . . . . .
H70A H -0.049515 0.583416 0.077512 0.061 Uiso 1 1 calc R U . . .
H70B H -0.055112 0.636226 0.150174 0.061 Uiso 1 1 calc R U . . .
H70C H -0.001547 0.681120 0.103629 0.061 Uiso 1 1 calc R U . . .
C10 C 0.1711(3) -0.00144(16) 0.41825(12) 0.0433(7) Uani 1 1 d . . . . .
C69 C 0.1972(3) 0.58399(18) 0.06038(14) 0.0451(7) Uani 1 1 d . . . . .
H69A H 0.156352 0.540577 0.025313 0.068 Uiso 1 1 calc R U . . .
H69B H 0.200240 0.639111 0.052948 0.068 Uiso 1 1 calc R U . . .
H69C H 0.281776 0.565166 0.064969 0.068 Uiso 1 1 calc R U . . .
C45 C 0.7723(3) -0.14088(17) 0.37833(13) 0.0424(6) Uani 1 1 d . . . . .
H45A H 0.828891 -0.129352 0.348710 0.064 Uiso 1 1 calc R U . . .
H45B H 0.792504 -0.102552 0.420275 0.064 Uiso 1 1 calc R U . . .
H45C H 0.781095 -0.201046 0.376108 0.064 Uiso 1 1 calc R U . . .
C44 C 0.5539(4) -0.1434(2) 0.4095(2) 0.0801(14) Uani 1 1 d . . . . .
H44A H 0.467456 -0.133544 0.400334 0.120 Uiso 1 1 calc R U . . .
H44B H 0.564129 -0.203543 0.407058 0.120 Uiso 1 1 calc R U . . .
H44C H 0.575538 -0.105049 0.451226 0.120 Uiso 1 1 calc R U . . .
C68 C 0.1879(4) 0.66246(17) 0.17368(16) 0.0567(9) Uani 1 1 d . . . . .
H68A H 0.271426 0.642378 0.178861 0.085 Uiso 1 1 calc R U . . .
H68B H 0.193788 0.716705 0.165134 0.085 Uiso 1 1 calc R U . . .
H68C H 0.140222 0.671811 0.211678 0.085 Uiso 1 1 calc R U . . .
C46 C 0.6105(4) -0.18681(17) 0.29706(19) 0.0757(13) Uani 1 1 d . . . . .
H46A H 0.665774 -0.174079 0.267438 0.114 Uiso 1 1 calc R U . . .
H46B H 0.623569 -0.246363 0.295492 0.114 Uiso 1 1 calc R U . . .
H46C H 0.524018 -0.179582 0.286413 0.114 Uiso 1 1 calc R U . . .
N2 N 0.71277(16) 0.56200(11) 0.37905(8) 0.0209(4) Uani 1 1 d . . . . .
N1 N 0.06030(19) -0.00920(11) 0.32664(9) 0.0290(4) Uani 1 1 d . . . . .
N3 N 0.20619(17) -0.07642(11) 0.13330(9) 0.0239(4) Uani 1 1 d . . . . .
F5 F 0.62267(17) 0.61237(10) 0.53333(7) 0.0457(4) Uani 1 1 d . . . . .
F6 F 0.50669(17) 0.64372(11) 0.46964(7) 0.0534(5) Uani 1 1 d . . . . .
F4 F 0.6905(2) 0.69461(10) 0.48610(9) 0.0701(7) Uani 1 1 d . . . . .
F2 F 0.24304(17) -0.06632(11) 0.38818(8) 0.0497(4) Uani 1 1 d . . . . .
F3 F 0.0849(2) -0.03413(14) 0.44526(10) 0.0746(7) Uani 1 1 d . . . . .
F1 F 0.2428(3) 0.05187(12) 0.46264(9) 0.0887(9) Uani 1 1 d . . . . .
C74 C 0.50369(19) 0.37211(13) 0.21741(10) 0.0202(4) Uani 1 1 d . . . . .
C80 C 0.48922(19) 0.46283(13) 0.23591(10) 0.0208(4) Uani 1 1 d . . . . .
C73 C 0.5555(2) 0.32870(13) 0.15800(10) 0.0246(4) Uani 1 1 d . . . . .
C84 C 0.5852(2) 0.16073(15) 0.12155(11) 0.0302(5) Uani 1 1 d . . . . .
C79 C 0.4374(2) 0.50939(13) 0.29521(10) 0.0227(4) Uani 1 1 d . . . . .
C89 C 0.5718(2) -0.06171(15) 0.12751(11) 0.0304(5) Uani 1 1 d . . . . .
H89 H 0.549634 -0.089010 0.156404 0.036 Uiso 1 1 calc R U . . .
C83 C 0.5733(2) 0.23710(14) 0.13749(10) 0.0284(5) Uani 1 1 d . . . . .
C78 C 0.3996(2) 0.46346(14) 0.33175(10) 0.0256(4) Uani 1 1 d . . . . .
H78 H 0.363040 0.493246 0.370740 0.031 Uiso 1 1 calc R U . . .
C86 C 0.6368(3) 0.01904(15) 0.04471(12) 0.0347(6) Uani 1 1 d . . . . .
H86 H 0.659699 0.046322 0.015916 0.042 Uiso 1 1 calc R U . . .
C90 C 0.5647(2) 0.02688(15) 0.14505(11) 0.0299(5) Uani 1 1 d . . . . .
H90 H 0.538015 0.059623 0.185618 0.036 Uiso 1 1 calc R U . . .
C88 C 0.6106(2) -0.11237(14) 0.06842(10) 0.0251(4) Uani 1 1 d . . . . .
C85 C 0.5964(2) 0.06862(14) 0.10367(11) 0.0276(5) Uani 1 1 d . . . . .
C91 C 0.6127(2) -0.21119(14) 0.05050(11) 0.0286(5) Uani 1 1 d . . . . .
C87 C 0.6436(2) -0.07019(15) 0.02794(11) 0.0329(5) Uani 1 1 d . . . . .
H87 H 0.671538 -0.103039 -0.012359 0.040 Uiso 1 1 calc R U . . .
C75 C 0.4660(2) 0.32848(13) 0.25778(10) 0.0230(4) Uani 1 1 d . . . . .
H75 H 0.477341 0.267907 0.246302 0.028 Uiso 1 1 calc R U . . .
C77 C 0.4135(2) 0.37339(14) 0.31320(10) 0.0253(4) Uani 1 1 d . . . . .
H77 H 0.385942 0.343549 0.339656 0.030 Uiso 1 1 calc R U . . .
C82 C 0.4277(2) 0.60564(14) 0.31596(11) 0.0298(5) Uani 1 1 d . . . . .
H82A H 0.374339 0.626017 0.352530 0.045 Uiso 1 1 calc R U . . .
H82B H 0.391875 0.622728 0.282579 0.045 Uiso 1 1 calc R U . . .
H82C H 0.510529 0.631159 0.326348 0.045 Uiso 1 1 calc R U . . .
C71 C 0.5669(2) 0.46572(15) 0.14472(11) 0.0285(5) Uani 1 1 d . . . . .
C72 C 0.5876(2) 0.37674(15) 0.12158(10) 0.0286(5) Uani 1 1 d . . . . .
H72 H 0.622931 0.350150 0.081782 0.034 Uiso 1 1 calc R U . . .
C92 C 0.4789(3) -0.24317(17) 0.05109(14) 0.0449(7) Uani 1 1 d . . . . .
H92A H 0.443194 -0.215875 0.092322 0.067 Uiso 1 1 calc R U . . .
H92B H 0.429194 -0.228095 0.020433 0.067 Uiso 1 1 calc R U . . .
H92C H 0.478925 -0.305936 0.040890 0.067 Uiso 1 1 calc R U . . .
C81 C 0.6019(3) 0.51930(18) 0.10549(13) 0.0398(6) Uani 1 1 d . . . . .
C93 C 0.6651(3) -0.25474(15) -0.01400(12) 0.0362(6) Uani 1 1 d . . . . .
H93A H 0.614354 -0.239526 -0.044270 0.054 Uiso 1 1 calc R U . . .
H93B H 0.750624 -0.235321 -0.015458 0.054 Uiso 1 1 calc R U . . .
H93C H 0.663904 -0.317437 -0.023843 0.054 Uiso 1 1 calc R U . . .
C94 C 0.6943(3) -0.23659(17) 0.09606(14) 0.0468(7) Uani 1 1 d . . . . .
H94A H 0.662653 -0.209330 0.138159 0.070 Uiso 1 1 calc R U . . .
H94B H 0.692980 -0.299417 0.085437 0.070 Uiso 1 1 calc R U . . .
H94C H 0.779700 -0.217300 0.093823 0.070 Uiso 1 1 calc R U . . .
N4 N 0.52124(18) 0.50914(11) 0.19884(9) 0.0246(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
C11 C8 1.506(3) . ?
F11A C81 1.341(4) . ?
F10A C81 1.287(4) . ?
F12A C81 1.314(4) . ?
F7A C56 1.316(4) . ?
F9A C56 1.301(3) . ?
F8A C56 1.301(4) . ?
F11B C81 1.377(6) . ?
F12B C81 1.272(6) . ?
F10B C81 1.303(7) . ?
F7B C56 1.246(8) . ?
F9B C56 1.307(6) . ?
F8B C56 1.326(7) . ?
C27 C28 1.406(3) . ?
C27 C33 1.423(3) . ?
C27 C26 1.429(3) . ?
C50 C51 1.416(3) . ?
C50 C55 1.426(3) . ?
C50 C49 1.428(3) . ?
C33 N2 1.366(3) . ?
C33 C32 1.430(3) . ?
C55 N3 1.366(3) . ?
C55 C54 1.428(3) . ?
C12 C13 1.193(3) . ?
C12 C3 1.434(3) . ?
C32 C31 1.366(3) . ?
C32 C36 1.501(3) . ?
C53 C54 1.375(3) . ?
C53 C52 1.404(3) . ?
C25 C26 1.377(3) . ?
C25 C24 1.405(3) . ?
C13 C14 1.440(3) . ?
C31 C29 1.415(3) . ?
C49 C48 1.378(3) . ?
C49 C58 1.433(3) . ?
C64 C65 1.396(3) . ?
C64 C62 1.401(3) . ?
C64 C67 1.537(3) . ?
C24 N2 1.312(3) . ?
C24 C34 1.512(3) . ?
C39 C40A 1.386(3) . ?
C39 C40 1.392(3) . ?
C39 C38 1.442(3) . ?
C54 C57 1.499(3) . ?
C59 C58 1.195(3) . ?
C59 C60 1.441(3) . ?
C17 C16 1.398(3) . ?
C17 C18 1.404(3) . ?
C17 C20 1.533(3) . ?
C51 C52 1.364(3) . ?
C47 N3 1.315(3) . ?
C47 C48 1.403(3) . ?
C47 C56 1.513(3) . ?
C4 C5 1.418(3) . ?
C4 C3 1.425(3) . ?
C4 C9 1.426(3) . ?
C9 N1 1.359(3) . ?
C9 C8 1.439(3) . ?
C66 C60 1.388(3) . ?
C66 C65 1.391(3) . ?
C19 C18 1.384(3) . ?
C19 C14 1.395(3) . ?
C38 C37 1.192(3) . ?
C60 C61 1.397(3) . ?
C42 C41 1.385(4) . ?
C42 C43 1.386(4) . ?
C42 C43A 1.539(3) . ?
C28 C29 1.365(3) . ?
C15 C16 1.388(3) . ?
C15 C14 1.393(3) . ?
C26 C37 1.435(3) . ?
C40A C43 1.379(3) . ?
C40 C41 1.395(3) . ?
C62 C61 1.386(3) . ?
C20 C23 1.530(3) . ?
C20 C22 1.531(3) . ?
C20 C21 1.537(3) . ?
C34 F4 1.313(3) . ?
C34 F6 1.333(3) . ?
C34 F5 1.335(3) . ?
C3 C2 1.375(3) . ?
C5 C6 1.369(3) . ?
C7 C8 1.367(4) . ?
C7 C6 1.403(4) . ?
C1 N1 1.319(3) . ?
C1 C2 1.408(3) . ?
C1 C10 1.506(4) . ?
C67 C68 1.515(4) . ?
C67 C70 1.536(4) . ?
C67 C69 1.544(4) . ?
C43A C44 1.523(5) . ?
C43A C45 1.527(4) . ?
C43A C46 1.534(4) . ?
C10 F2 1.313(3) . ?
C10 F3 1.329(4) . ?
C10 F1 1.340(3) . ?
C74 C75 1.412(3) . ?
C74 C80 1.418(3) . ?
C74 C73 1.424(3) . ?
C80 N4 1.367(3) . ?
C80 C79 1.432(3) . ?
C73 C72 1.377(3) . ?
C73 C83 1.434(3) . ?
C84 C83 1.193(3) . ?
C84 C85 1.437(3) . ?
C79 C78 1.369(3) . ?
C79 C82 1.497(3) . ?
C89 C90 1.379(3) . ?
C89 C88 1.396(3) . ?
C78 C77 1.407(3) . ?
C86 C87 1.390(3) . ?
C86 C85 1.394(3) . ?
C90 C85 1.392(3) . ?
C88 C87 1.383(3) . ?
C88 C91 1.539(3) . ?
C91 C93 1.520(3) . ?
C91 C94 1.528(4) . ?
C91 C92 1.537(4) . ?
C75 C77 1.361(3) . ?
C71 N4 1.304(3) . ?
C71 C72 1.398(3) . ?
C71 C81 1.508(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
C28 C27 C33 119.65(19) . . ?
C28 C27 C26 122.46(19) . . ?
C33 C27 C26 117.89(19) . . ?
C51 C50 C55 119.4(2) . . ?
C51 C50 C49 122.80(19) . . ?
C55 C50 C49 117.81(19) . . ?
N2 C33 C27 122.39(19) . . ?
N2 C33 C32 118.03(18) . . ?
C27 C33 C32 119.58(19) . . ?
N3 C55 C50 122.23(19) . . ?
N3 C55 C54 118.25(18) . . ?
C50 C55 C54 119.51(19) . . ?
C13 C12 C3 178.9(2) . . ?
C31 C32 C33 118.38(19) . . ?
C31 C32 C36 121.61(19) . . ?
C33 C32 C36 120.00(19) . . ?
C54 C53 C52 121.6(2) . . ?
C26 C25 C24 118.39(19) . . ?
C12 C13 C14 178.7(3) . . ?
C32 C31 C29 122.0(2) . . ?
C48 C49 C50 119.04(18) . . ?
C48 C49 C58 121.3(2) . . ?
C50 C49 C58 119.67(19) . . ?
C65 C64 C62 117.48(18) . . ?
C65 C64 C67 122.60(19) . . ?
C62 C64 C67 119.80(19) . . ?
N2 C24 C25 125.6(2) . . ?
N2 C24 C34 114.66(18) . . ?
C25 C24 C34 119.66(19) . . ?
C40A C39 C40 118.3(2) . . ?
C40A C39 C38 120.1(2) . . ?
C40 C39 C38 121.5(2) . . ?
C53 C54 C55 118.68(19) . . ?
C53 C54 C57 121.1(2) . . ?
C55 C54 C57 120.2(2) . . ?
C58 C59 C60 175.7(2) . . ?
C16 C17 C18 117.08(19) . . ?
C16 C17 C20 122.74(19) . . ?
C18 C17 C20 120.05(18) . . ?
C52 C51 C50 119.92(19) . . ?
N3 C47 C48 126.0(2) . . ?
N3 C47 C56 114.82(19) . . ?
C48 C47 C56 119.2(2) . . ?
C5 C4 C3 122.7(2) . . ?
C5 C4 C9 119.3(2) . . ?
C3 C4 C9 118.0(2) . . ?
C59 C58 C49 178.1(2) . . ?
N1 C9 C4 122.2(2) . . ?
N1 C9 C8 118.4(2) . . ?
C4 C9 C8 119.4(2) . . ?
C60 C66 C65 120.4(2) . . ?
C18 C19 C14 120.4(2) . . ?
C37 C38 C39 176.3(3) . . ?
C66 C60 C61 119.10(18) . . ?
C66 C60 C59 120.1(2) . . ?
C61 C60 C59 120.78(19) . . ?
C41 C42 C43 116.9(2) . . ?
C41 C42 C43A 122.6(2) . . ?
C43 C42 C43A 120.3(2) . . ?
C29 C28 C27 120.19(19) . . ?
C49 C48 C47 117.8(2) . . ?
C16 C15 C14 120.4(2) . . ?
C25 C26 C27 118.57(18) . . ?
C25 C26 C37 121.53(19) . . ?
C27 C26 C37 119.87(19) . . ?
C28 C29 C31 120.1(2) . . ?
C15 C16 C17 121.7(2) . . ?
C51 C52 C53 120.9(2) . . ?
C43 C40A C39 120.9(2) . . ?
C38 C37 C26 176.3(2) . . ?
C66 C65 C64 121.3(2) . . ?
C39 C40 C41 119.8(2) . . ?
C15 C14 C19 118.80(19) . . ?
C15 C14 C13 120.1(2) . . ?
C19 C14 C13 121.1(2) . . ?
C19 C18 C17 121.6(2) . . ?
C61 C62 C64 121.6(2) . . ?
C23 C20 C22 108.41(19) . . ?
C23 C20 C17 106.94(18) . . ?
C22 C20 C17 112.41(18) . . ?
C23 C20 C21 109.5(2) . . ?
C22 C20 C21 108.45(19) . . ?
C17 C20 C21 111.05(18) . . ?
C62 C61 C60 120.0(2) . . ?
F4 C34 F6 107.4(2) . . ?
F4 C34 F5 107.3(2) . . ?
F6 C34 F5 104.86(19) . . ?
F4 C34 C24 113.78(19) . . ?
F6 C34 C24 111.3(2) . . ?
F5 C34 C24 111.78(19) . . ?
C2 C3 C4 118.9(2) . . ?
C2 C3 C12 120.7(2) . . ?
C4 C3 C12 120.3(2) . . ?
C6 C5 C4 120.1(2) . . ?
C40A C43 C42 121.9(2) . . ?
C8 C7 C6 122.3(2) . . ?
N1 C1 C2 125.1(2) . . ?
N1 C1 C10 114.7(2) . . ?
C2 C1 C10 120.2(2) . . ?
C3 C2 C1 118.2(2) . . ?
F9A C56 F8A 105.0(3) . . ?
F7B C56 F9B 107.4(5) . . ?
F9A C56 F7A 103.7(3) . . ?
F8A C56 F7A 107.9(3) . . ?
F7B C56 F8B 111.5(6) . . ?
F9B C56 F8B 98.4(5) . . ?
F7B C56 C47 113.7(4) . . ?
F9A C56 C47 114.0(2) . . ?
F8A C56 C47 112.5(2) . . ?
F9B C56 C47 114.2(3) . . ?
F7A C56 C47 113.1(2) . . ?
F8B C56 C47 110.6(3) . . ?
C7 C8 C9 118.4(2) . . ?
C7 C8 C11 121.9(2) . . ?
C9 C8 C11 119.7(2) . . ?
C42 C41 C40 122.1(2) . . ?
C68 C67 C70 109.3(2) . . ?
C68 C67 C64 112.4(2) . . ?
C70 C67 C64 110.92(19) . . ?
C68 C67 C69 108.6(2) . . ?
C70 C67 C69 108.2(2) . . ?
C64 C67 C69 107.28(19) . . ?
C5 C6 C7 120.5(2) . . ?
C44 C43A C45 107.9(3) . . ?
C44 C43A C46 110.4(3) . . ?
C45 C43A C46 107.8(3) . . ?
C44 C43A C42 111.9(2) . . ?
C45 C43A C42 107.4(2) . . ?
C46 C43A C42 111.3(2) . . ?
F2 C10 F3 105.9(2) . . ?
F2 C10 F1 105.5(3) . . ?
F3 C10 F1 108.2(3) . . ?
F2 C10 C1 113.0(2) . . ?
F3 C10 C1 111.8(3) . . ?
F1 C10 C1 112.1(2) . . ?
C24 N2 C33 117.17(17) . . ?
C1 N1 C9 117.60(19) . . ?
C47 N3 C55 117.10(18) . . ?
C75 C74 C80 119.39(19) . . ?
C75 C74 C73 122.73(19) . . ?
C80 C74 C73 117.87(19) . . ?
N4 C80 C74 122.66(19) . . ?
N4 C80 C79 117.36(18) . . ?
C74 C80 C79 119.97(19) . . ?
C72 C73 C74 118.4(2) . . ?
C72 C73 C83 121.6(2) . . ?
C74 C73 C83 119.9(2) . . ?
C83 C84 C85 178.2(3) . . ?
C78 C79 C80 118.07(19) . . ?
C78 C79 C82 122.0(2) . . ?
C80 C79 C82 119.94(19) . . ?
C90 C89 C88 121.8(2) . . ?
C84 C83 C73 178.1(3) . . ?
C79 C78 C77 121.9(2) . . ?
C87 C86 C85 120.2(2) . . ?
C89 C90 C85 120.4(2) . . ?
C87 C88 C89 117.4(2) . . ?
C87 C88 C91 122.9(2) . . ?
C89 C88 C91 119.7(2) . . ?
C90 C85 C86 118.6(2) . . ?
C90 C85 C84 120.1(2) . . ?
C86 C85 C84 121.3(2) . . ?
C93 C91 C94 107.7(2) . . ?
C93 C91 C92 108.0(2) . . ?
C94 C91 C92 111.0(2) . . ?
C93 C91 C88 111.98(19) . . ?
C94 C91 C88 109.70(19) . . ?
C92 C91 C88 108.5(2) . . ?
C88 C87 C86 121.7(2) . . ?
C77 C75 C74 119.86(19) . . ?
C75 C77 C78 120.8(2) . . ?
N4 C71 C72 126.1(2) . . ?
N4 C71 C81 115.0(2) . . ?
C72 C71 C81 118.9(2) . . ?
C73 C72 C71 118.2(2) . . ?
F12B C81 F10B 109.8(5) . . ?
F10A C81 F12A 107.1(3) . . ?
F10A C81 F11A 107.4(3) . . ?
F12A C81 F11A 104.8(3) . . ?
F12B C81 F11B 104.1(4) . . ?
F10B C81 F11B 103.2(4) . . ?
F12B C81 C71 114.6(4) . . ?
F10A C81 C71 112.3(2) . . ?
F10B C81 C71 113.6(5) . . ?
F12A C81 C71 112.0(2) . . ?
F11A C81 C71 112.7(2) . . ?
F11B C81 C71 110.7(3) . . ?
C71 N4 C80 116.64(18) . . ?

_refine_diff_density_max         0.753
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.050

