# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

####################################################################### 
# 
# 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_2T1F
_database_code_depnum_ccdc_archive 'CCDC 981582'
_audit_update_record             
;
2016-03-09 deposited with the CCDC.
2016-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 F4 N O'
_chemical_formula_sum            'C14 H9 F4 N O'
_chemical_formula_weight         283.22

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.6922(3)
_cell_length_b                   8.9547(2)
_cell_length_c                   21.1831(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2407.56(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2585
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      32.76

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.141
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12867
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.505
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2118
_reflns_number_gt                1721
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR 92'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2013)'
_computing_molecular_graphics    Mercury
_computing_publication_material  Mercury
_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)+(0.0461P)²+1.1375P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0061(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2118
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1070
_refine_ls_wR_factor_gt          0.0953
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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
F2 F 1.22185(10) 0.58895(15) 0.64047(6) 0.0449(4) Uani 1 1 d . . . . .
F4 F 1.25138(9) 0.54470(15) 0.54216(6) 0.0455(4) Uani 1 1 d . . . . .
F3 F 1.17958(9) 0.37723(13) 0.60059(6) 0.0372(3) Uani 1 1 d . . . . .
N1 N 0.80047(12) 0.51762(17) 0.62204(7) 0.0245(4) Uani 1 1 d . . . . .
H1 H 0.8104 0.4244 0.6338 0.029 Uiso 1 1 calc R U . . .
O1 O 0.67605(11) 0.70173(15) 0.61946(7) 0.0356(4) Uani 1 1 d . . . . .
F1A F 0.76028(15) 0.3703(2) 0.73568(9) 0.0360(4) Uani 0.577(2) 1 d . . P A -1
C1A C 0.63181(14) 0.4741(2) 0.67025(8) 0.0226(4) Uani 0.577(2) 1 d . . P A -1
C2A C 0.52427(15) 0.4759(2) 0.65611(9) 0.0256(4) Uani 0.577(2) 1 d . . P A -1
H2A H 0.4992 0.5430 0.6248 0.031 Uiso 0.577(2) 1 calc R U P A -1
C3A C 0.45355(16) 0.3837(2) 0.68610(10) 0.0310(5) Uani 0.577(2) 1 d . . P A -1
H3A H 0.3811 0.3860 0.6748 0.037 Uiso 0.577(2) 1 calc R U P A -1
C4A C 0.48831(17) 0.2874(2) 0.73282(10) 0.0358(5) Uani 0.577(2) 1 d . . P A -1
H4A H 0.4398 0.2234 0.7536 0.043 Uiso 0.577(2) 1 calc R U P A -1
C5A C 0.59387(18) 0.2846(2) 0.74918(9) 0.0362(5) Uani 0.577(2) 1 d . . P A -1
H5A H 0.6181 0.2198 0.7816 0.043 Uiso 0.577(2) 1 calc R U P A -1
C6A C 0.66355(15) 0.3769(2) 0.71784(9) 0.0291(5) Uani 0.577(2) 1 d . . P A -1
F1B F 0.4884(2) 0.5614(3) 0.61329(13) 0.0360(4) Uani 0.423(2) 1 d . . P A -2
C1B C 0.63181(14) 0.4741(2) 0.67025(8) 0.0226(4) Uani 0.423(2) 1 d . . P A -2
C6B C 0.52427(15) 0.4759(2) 0.65611(9) 0.0256(4) Uani 0.423(2) 1 d . . P A -2
C5B C 0.45355(16) 0.3837(2) 0.68610(10) 0.0310(5) Uani 0.423(2) 1 d . . P A -2
H5B H 0.3811 0.3860 0.6748 0.037 Uiso 0.423(2) 1 calc R U P A -2
C4B C 0.48831(17) 0.2874(2) 0.73282(10) 0.0358(5) Uani 0.423(2) 1 d . . P A -2
H4B H 0.4398 0.2234 0.7536 0.043 Uiso 0.423(2) 1 calc R U P A -2
C3B C 0.59387(18) 0.2846(2) 0.74918(9) 0.0362(5) Uani 0.423(2) 1 d . . P A -2
H3B H 0.6181 0.2198 0.7816 0.043 Uiso 0.423(2) 1 calc R U P A -2
C2B C 0.66355(15) 0.3769(2) 0.71784(9) 0.0291(5) Uani 0.423(2) 1 d . . P A -2
H2B H 0.7359 0.3740 0.7292 0.035 Uiso 0.423(2) 1 calc R U P A -2
C7 C 0.88718(15) 0.5876(2) 0.59186(8) 0.0223(4) Uani 1 1 d . . . . .
C8 C 0.87661(15) 0.7087(2) 0.55085(8) 0.0252(4) Uani 1 1 d . . . . .
H8 H 0.8093 0.7513 0.5431 0.030 Uiso 1 1 calc R U . . .
C9 C 0.96554(15) 0.7662(2) 0.52145(9) 0.0279(5) Uani 1 1 d . . . . .
H9 H 0.9583 0.8484 0.4934 0.033 Uiso 1 1 calc R U . . .
C10 C 1.06449(16) 0.7067(2) 0.53208(9) 0.0276(5) Uani 1 1 d . . . . .
H10 H 1.1247 0.7475 0.5118 0.033 Uiso 1 1 calc R U . . .
C11 C 1.07418(15) 0.5858(2) 0.57293(9) 0.0251(4) Uani 1 1 d . . . . .
C12 C 0.98613(15) 0.5259(2) 0.60247(8) 0.0236(4) Uani 1 1 d . . . . .
H12 H 0.9935 0.4427 0.6299 0.028 Uiso 1 1 calc R U . . .
C13 C 0.70446(15) 0.5758(2) 0.63510(8) 0.0231(4) Uani 1 1 d . . . . .
C14 C 1.18048(16) 0.5237(2) 0.58835(9) 0.0301(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F2 C14 1.355(2) . ?
F4 C14 1.342(2) . ?
F3 C14 1.337(2) . ?
N1 C13 1.354(2) . ?
N1 C7 1.419(2) . ?
N1 H1 0.8800 . ?
O1 C13 1.229(2) . ?
F1A C6A 1.286(3) . ?
C1A C6A 1.391(3) . ?
C1A C2A 1.398(3) . ?
C1A C13 1.494(3) . ?
C2A C3A 1.375(3) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.385(3) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.384(3) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.381(3) . ?
C5A H5A 0.9500 . ?
F1B C6B 1.272(3) . ?
C1B C2B 1.391(3) . ?
C1B C6B 1.398(3) . ?
C1B C13 1.494(3) . ?
C6B C5B 1.375(3) . ?
C5B C4B 1.385(3) . ?
C5B H5B 0.9500 . ?
C4B C3B 1.384(3) . ?
C4B H4B 0.9500 . ?
C3B C2B 1.381(3) . ?
C3B H3B 0.9500 . ?
C2B H2B 0.9500 . ?
C7 C12 1.390(3) . ?
C7 C8 1.396(3) . ?
C8 C9 1.388(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.383(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.391(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(3) . ?
C11 C14 1.495(3) . ?
C12 H12 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
C13 N1 C7 128.34(16) . . ?
C13 N1 H1 115.8 . . ?
C7 N1 H1 115.8 . . ?
C6A C1A C2A 116.44(18) . . ?
C6A C1A C13 124.29(17) . . ?
C2A C1A C13 119.26(16) . . ?
C3A C2A C1A 122.11(18) . . ?
C3A C2A H2A 118.9 . . ?
C1A C2A H2A 118.9 . . ?
C2A C3A C4A 119.74(19) . . ?
C2A C3A H3A 120.1 . . ?
C4A C3A H3A 120.1 . . ?
C5A C4A C3A 119.91(19) . . ?
C5A C4A H4A 120.0 . . ?
C3A C4A H4A 120.0 . . ?
C6A C5A C4A 119.25(19) . . ?
C6A C5A H5A 120.4 . . ?
C4A C5A H5A 120.4 . . ?
F1A C6A C5A 116.27(19) . . ?
F1A C6A C1A 121.21(19) . . ?
C5A C6A C1A 122.52(19) . . ?
C2B C1B C6B 116.44(18) . . ?
C2B C1B C13 124.29(17) . . ?
C6B C1B C13 119.26(16) . . ?
F1B C6B C5B 117.2(2) . . ?
F1B C6B C1B 120.7(2) . . ?
C5B C6B C1B 122.11(18) . . ?
C6B C5B C4B 119.74(19) . . ?
C6B C5B H5B 120.1 . . ?
C4B C5B H5B 120.1 . . ?
C3B C4B C5B 119.91(19) . . ?
C3B C4B H4B 120.0 . . ?
C5B C4B H4B 120.0 . . ?
C2B C3B C4B 119.25(19) . . ?
C2B C3B H3B 120.4 . . ?
C4B C3B H3B 120.4 . . ?
C3B C2B C1B 122.52(19) . . ?
C3B C2B H2B 118.7 . . ?
C1B C2B H2B 118.7 . . ?
C12 C7 C8 119.74(17) . . ?
C12 C7 N1 116.90(16) . . ?
C8 C7 N1 123.30(17) . . ?
C9 C8 C7 119.30(18) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C10 C9 C8 121.48(18) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C11 118.80(18) . . ?
C9 C10 H10 120.6 . . ?
C11 C10 H10 120.6 . . ?
C12 C11 C10 120.64(18) . . ?
C12 C11 C14 118.95(17) . . ?
C10 C11 C14 120.33(17) . . ?
C11 C12 C7 120.04(17) . . ?
C11 C12 H12 120.0 . . ?
C7 C12 H12 120.0 . . ?
O1 C13 N1 124.18(18) . . ?
O1 C13 C1B 120.81(17) . . ?
N1 C13 C1B 115.01(16) . . ?
O1 C13 C1A 120.81(17) . . ?
N1 C13 C1A 115.01(16) . . ?
F3 C14 F4 106.52(16) . . ?
F3 C14 F2 105.56(16) . . ?
F4 C14 F2 105.88(16) . . ?
F3 C14 C11 113.55(16) . . ?
F4 C14 C11 113.17(16) . . ?
F2 C14 C11 111.55(17) . . ?

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
C6A C1A C2A C3A -1.9(3) . . . . ?
C13 C1A C2A C3A 179.08(17) . . . . ?
C1A C2A C3A C4A 1.3(3) . . . . ?
C2A C3A C4A C5A 0.1(3) . . . . ?
C3A C4A C5A C6A -0.9(3) . . . . ?
C4A C5A C6A F1A 179.2(2) . . . . ?
C4A C5A C6A C1A 0.3(3) . . . . ?
C2A C1A C6A F1A -177.84(19) . . . . ?
C13 C1A C6A F1A 1.2(3) . . . . ?
C2A C1A C6A C5A 1.1(3) . . . . ?
C13 C1A C6A C5A -179.95(18) . . . . ?
C2B C1B C6B F1B 180.0(2) . . . . ?
C13 C1B C6B F1B 0.9(3) . . . . ?
C2B C1B C6B C5B -1.9(3) . . . . ?
C13 C1B C6B C5B 179.08(17) . . . . ?
F1B C6B C5B C4B 179.5(2) . . . . ?
C1B C6B C5B C4B 1.3(3) . . . . ?
C6B C5B C4B C3B 0.1(3) . . . . ?
C5B C4B C3B C2B -0.9(3) . . . . ?
C4B C3B C2B C1B 0.3(3) . . . . ?
C6B C1B C2B C3B 1.1(3) . . . . ?
C13 C1B C2B C3B -179.95(18) . . . . ?
C13 N1 C7 C12 158.84(18) . . . . ?
C13 N1 C7 C8 -24.0(3) . . . . ?
C12 C7 C8 C9 -0.3(3) . . . . ?
N1 C7 C8 C9 -177.40(17) . . . . ?
C7 C8 C9 C10 -0.3(3) . . . . ?
C8 C9 C10 C11 0.4(3) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C9 C10 C11 C14 -176.63(18) . . . . ?
C10 C11 C12 C7 -0.6(3) . . . . ?
C14 C11 C12 C7 176.10(17) . . . . ?
C8 C7 C12 C11 0.8(3) . . . . ?
N1 C7 C12 C11 178.03(16) . . . . ?
C7 N1 C13 O1 3.4(3) . . . . ?
C7 N1 C13 C1B -177.29(16) . . . . ?
C7 N1 C13 C1A -177.29(16) . . . . ?
C2B C1B C13 O1 -142.8(2) . . . . ?
C6B C1B C13 O1 36.2(3) . . . . ?
C2B C1B C13 N1 37.8(3) . . . . ?
C6B C1B C13 N1 -143.21(18) . . . . ?
C6A C1A C13 O1 -142.8(2) . . . . ?
C2A C1A C13 O1 36.2(3) . . . . ?
C6A C1A C13 N1 37.8(3) . . . . ?
C2A C1A C13 N1 -143.21(18) . . . . ?
C12 C11 C14 F3 33.8(2) . . . . ?
C10 C11 C14 F3 -149.43(17) . . . . ?
C12 C11 C14 F4 155.41(17) . . . . ?
C10 C11 C14 F4 -27.8(3) . . . . ?
C12 C11 C14 F2 -85.3(2) . . . . ?
C10 C11 C14 F2 91.4(2) . . . . ?

_refine_diff_density_max         0.232
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_2T1F_w
_database_code_depnum_ccdc_archive 'CCDC 981583'
_audit_update_record             
;
2016-03-09 deposited with the CCDC.
2016-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 F4 N O1, 0.5(H2 O)'
_chemical_formula_sum            'C14 H10 F4 N O1.50'
_chemical_formula_weight         292.23

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_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+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   7.3568(17)
_cell_length_b                   27.672(6)
_cell_length_c                   12.434(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2531.2(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2952
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      28.24

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_F_000             1192
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.140
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13907
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.202
_diffrn_reflns_theta_max         28.240
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2952
_reflns_number_gt                2733
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR 92'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2013)'
_computing_molecular_graphics    Mercury
_computing_publication_material  Mercury
_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)+(0.0614P)²+1.9260P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2952
_refine_ls_number_parameters     222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_ref         0.1425
_refine_ls_wR_factor_gt          0.1396
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.108
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.19891(18) 0.30303(5) 0.43920(11) 0.0212(3) Uani 1 1 d . . . . .
H1 H 0.1574 0.2890 0.3807 0.025 Uiso 1 1 calc R U . . .
O1 O 0.29268(17) 0.28763(4) 0.61055(9) 0.0265(3) Uani 1 1 d . . . . .
F1A F 0.11540(17) 0.20153(4) 0.66116(9) 0.0291(3) Uani 0.822(2) 1 d . . P A 1
F1B F 0.3695(8) 0.2249(2) 0.3288(4) 0.0291(3) Uani 0.178(2) 1 d . . P A 2
F2A F 0.2666(7) 0.51181(8) 0.5869(2) 0.0678(16) Uani 0.626(9) 1 d . . P B 1
F3A F 0.1535(6) 0.45841(15) 0.6846(3) 0.0697(16) Uani 0.626(9) 1 d . . P B 1
F4A F 0.4350(5) 0.45736(18) 0.6501(4) 0.0849(18) Uani 0.626(9) 1 d . . P B 1
F2B F 0.2582(15) 0.43831(19) 0.7078(3) 0.086(3) Uani 0.374(9) 1 d . . P B 2
F3B F 0.4037(11) 0.4893(3) 0.6187(4) 0.080(4) Uani 0.374(9) 1 d . . P B 2
F4B F 0.1220(11) 0.4927(3) 0.6223(6) 0.108(5) Uani 0.374(9) 1 d . . P B 2
C1A C 0.2408(2) 0.22043(6) 0.49331(13) 0.0229(3) Uani 0.822(2) 1 d . . P A 1
C2A C 0.1793(2) 0.18664(6) 0.56732(14) 0.0267(4) Uani 0.822(2) 1 d . . P A 1
C3A C 0.1768(3) 0.13756(7) 0.54571(17) 0.0337(4) Uani 0.822(2) 1 d . . P A 1
H3A H 0.1331 0.1152 0.5977 0.040 Uiso 0.822(2) 1 calc R U P A 1
C4A C 0.2396(3) 0.12164(7) 0.44651(18) 0.0375(5) Uani 0.822(2) 1 d . . P A 1
H4A H 0.2395 0.0881 0.4306 0.045 Uiso 0.822(2) 1 calc R U P A 1
C5A C 0.3020(3) 0.15416(7) 0.37073(16) 0.0351(4) Uani 0.822(2) 1 d . . P A 1
H5A H 0.3446 0.1430 0.3030 0.042 Uiso 0.822(2) 1 calc R U P A 1
C6A C 0.3024(2) 0.20317(7) 0.39381(14) 0.0282(4) Uani 0.822(2) 1 d . . P A 1
H6A H 0.3452 0.2254 0.3414 0.034 Uiso 0.822(2) 1 calc R U P A 1
C1B C 0.2408(2) 0.22043(6) 0.49331(13) 0.0229(3) Uani 0.178(2) 1 d . . P A 2
C2B C 0.3024(2) 0.20317(7) 0.39381(14) 0.0282(4) Uani 0.178(2) 1 d . . P A 2
C3B C 0.3020(3) 0.15416(7) 0.37073(16) 0.0351(4) Uani 0.178(2) 1 d . . P A 2
H3B H 0.3446 0.1430 0.3030 0.042 Uiso 0.178(2) 1 calc R U P A 2
C4B C 0.2396(3) 0.12164(7) 0.44651(18) 0.0375(5) Uani 0.178(2) 1 d . . P A 2
H4B H 0.2395 0.0881 0.4306 0.045 Uiso 0.178(2) 1 calc R U P A 2
C5B C 0.1768(3) 0.13756(7) 0.54571(17) 0.0337(4) Uani 0.178(2) 1 d . . P A 2
H5B H 0.1331 0.1152 0.5977 0.040 Uiso 0.178(2) 1 calc R U P A 2
C6B C 0.1793(2) 0.18664(6) 0.56732(14) 0.0267(4) Uani 0.178(2) 1 d . . P A 2
H6B H 0.1375 0.1976 0.6354 0.032 Uiso 0.178(2) 1 calc R U P A 2
C7 C 0.2084(2) 0.35403(6) 0.43675(13) 0.0222(3) Uani 1 1 d . . . . .
C8 C 0.2341(2) 0.38286(6) 0.52708(13) 0.0239(3) Uani 1 1 d . . . . .
H8 H 0.2462 0.3687 0.5964 0.029 Uiso 1 1 calc R U . . .
C9 C 0.2419(2) 0.43277(6) 0.51416(14) 0.0283(4) Uani 1 1 d . . . . .
C10 C 0.2257(3) 0.45416(7) 0.41456(18) 0.0435(5) Uani 1 1 d . . . . .
H10 H 0.2318 0.4883 0.4073 0.052 Uiso 1 1 calc R U . . .
C11 C 0.2005(4) 0.42506(7) 0.32537(17) 0.0558(7) Uani 1 1 d . . . . .
H11 H 0.1897 0.4393 0.2561 0.067 Uiso 1 1 calc R U . . .
C12 C 0.1910(3) 0.37537(7) 0.33639(15) 0.0395(5) Uani 1 1 d . . . . .
H12 H 0.1724 0.3557 0.2747 0.047 Uiso 1 1 calc R U . . .
C13 C 0.2464(2) 0.27325(6) 0.52117(13) 0.0209(3) Uani 1 1 d . . . . .
C14 C 0.2687(3) 0.46368(7) 0.61160(16) 0.0367(4) Uani 1 1 d . . . . .
O2 O 0.0000 0.26695(6) 0.2500 0.0205(3) Uani 1 2 d S T P . .
H1W H 0.066(3) 0.2487(8) 0.2103(18) 0.036(6) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C13 1.356(2) . ?
N1 C7 1.413(2) . ?
N1 H1 0.8800 . ?
O1 C13 1.229(2) . ?
F1A C2A 1.324(2) . ?
F1B C2B 1.122(6) . ?
F2A C14 1.367(3) . ?
F3A C14 1.251(3) . ?
F4A C14 1.325(3) . ?
F2B C14 1.389(5) . ?
F3B C14 1.223(5) . ?
F4B C14 1.352(5) . ?
C1A C2A 1.388(2) . ?
C1A C6A 1.402(2) . ?
C1A C13 1.503(2) . ?
C2A C3A 1.384(3) . ?
C3A C4A 1.389(3) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.382(3) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.386(3) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C1B C6B 1.388(2) . ?
C1B C2B 1.402(2) . ?
C1B C13 1.503(2) . ?
C2B C3B 1.386(3) . ?
C3B C4B 1.382(3) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.389(3) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.384(3) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
C7 C12 1.387(2) . ?
C7 C8 1.391(2) . ?
C8 C9 1.392(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.378(3) . ?
C9 C14 1.496(2) . ?
C10 C11 1.383(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
O2 H1W 0.86(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
C13 N1 C7 127.60(13) . . ?
C13 N1 H1 116.2 . . ?
C7 N1 H1 116.2 . . ?
C2A C1A C6A 117.46(16) . . ?
C2A C1A C13 120.77(15) . . ?
C6A C1A C13 121.74(15) . . ?
F1A C2A C3A 118.15(16) . . ?
F1A C2A C1A 119.36(15) . . ?
C3A C2A C1A 122.46(17) . . ?
C2A C3A C4A 118.63(18) . . ?
C2A C3A H3A 120.7 . . ?
C4A C3A H3A 120.7 . . ?
C5A C4A C3A 120.64(17) . . ?
C5A C4A H4A 119.7 . . ?
C3A C4A H4A 119.7 . . ?
C4A C5A C6A 119.79(18) . . ?
C4A C5A H5A 120.1 . . ?
C6A C5A H5A 120.1 . . ?
C5A C6A C1A 121.03(18) . . ?
C5A C6A H6A 119.5 . . ?
C1A C6A H6A 119.5 . . ?
C6B C1B C2B 117.46(16) . . ?
C6B C1B C13 120.77(15) . . ?
C2B C1B C13 121.74(15) . . ?
F1B C2B C3B 112.1(3) . . ?
F1B C2B C1B 126.5(3) . . ?
C3B C2B C1B 121.03(18) . . ?
C4B C3B C2B 119.79(18) . . ?
C4B C3B H3B 120.1 . . ?
C2B C3B H3B 120.1 . . ?
C3B C4B C5B 120.64(17) . . ?
C3B C4B H4B 119.7 . . ?
C5B C4B H4B 119.7 . . ?
C6B C5B C4B 118.63(18) . . ?
C6B C5B H5B 120.7 . . ?
C4B C5B H5B 120.7 . . ?
C5B C6B C1B 122.46(17) . . ?
C5B C6B H6B 118.8 . . ?
C1B C6B H6B 118.8 . . ?
C12 C7 C8 119.67(15) . . ?
C12 C7 N1 116.12(14) . . ?
C8 C7 N1 124.21(15) . . ?
C7 C8 C9 118.80(16) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
C10 C9 C8 121.77(16) . . ?
C10 C9 C14 119.59(17) . . ?
C8 C9 C14 118.64(17) . . ?
C9 C10 C11 118.84(17) . . ?
C9 C10 H10 120.6 . . ?
C11 C10 H10 120.6 . . ?
C10 C11 C12 120.40(19) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C7 120.52(17) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?
O1 C13 N1 123.67(15) . . ?
O1 C13 C1B 122.07(15) . . ?
N1 C13 C1B 114.25(14) . . ?
O1 C13 C1A 122.07(15) . . ?
N1 C13 C1A 114.25(14) . . ?
F3A C14 F4A 110.4(3) . . ?
F3B C14 F4B 107.3(5) . . ?
F3A C14 F2A 105.6(3) . . ?
F4A C14 F2A 102.7(3) . . ?
F3B C14 F2B 106.0(4) . . ?
F4B C14 F2B 99.8(5) . . ?
F3B C14 C9 119.8(3) . . ?
F3A C14 C9 115.6(2) . . ?
F4A C14 C9 109.80(19) . . ?
F4B C14 C9 108.3(3) . . ?
F2A C14 C9 111.96(19) . . ?
F2B C14 C9 113.7(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6A C1A C2A F1A -178.20(15) . . . . ?
C13 C1A C2A F1A 3.9(2) . . . . ?
C6A C1A C2A C3A -0.3(2) . . . . ?
C13 C1A C2A C3A -178.19(15) . . . . ?
F1A C2A C3A C4A 178.49(16) . . . . ?
C1A C2A C3A C4A 0.5(3) . . . . ?
C2A C3A C4A C5A -0.4(3) . . . . ?
C3A C4A C5A C6A 0.1(3) . . . . ?
C4A C5A C6A C1A 0.2(3) . . . . ?
C2A C1A C6A C5A -0.1(2) . . . . ?
C13 C1A C6A C5A 177.80(15) . . . . ?
C6B C1B C2B F1B -173.2(4) . . . . ?
C13 C1B C2B F1B 4.7(5) . . . . ?
C6B C1B C2B C3B -0.1(2) . . . . ?
C13 C1B C2B C3B 177.80(15) . . . . ?
F1B C2B C3B C4B 174.2(4) . . . . ?
C1B C2B C3B C4B 0.2(3) . . . . ?
C2B C3B C4B C5B 0.1(3) . . . . ?
C3B C4B C5B C6B -0.4(3) . . . . ?
C4B C5B C6B C1B 0.5(3) . . . . ?
C2B C1B C6B C5B -0.3(2) . . . . ?
C13 C1B C6B C5B -178.19(15) . . . . ?
C13 N1 C7 C12 165.99(17) . . . . ?
C13 N1 C7 C8 -13.8(3) . . . . ?
C12 C7 C8 C9 0.0(3) . . . . ?
N1 C7 C8 C9 179.73(15) . . . . ?
C7 C8 C9 C10 -0.4(3) . . . . ?
C7 C8 C9 C14 179.72(16) . . . . ?
C8 C9 C10 C11 0.2(3) . . . . ?
C14 C9 C10 C11 -179.8(2) . . . . ?
C9 C10 C11 C12 0.3(4) . . . . ?
C10 C11 C12 C7 -0.6(4) . . . . ?
C8 C7 C12 C11 0.5(3) . . . . ?
N1 C7 C12 C11 -179.3(2) . . . . ?
C7 N1 C13 O1 6.0(3) . . . . ?
C7 N1 C13 C1B -173.05(14) . . . . ?
C7 N1 C13 C1A -173.05(14) . . . . ?
C6B C1B C13 O1 39.3(2) . . . . ?
C2B C1B C13 O1 -138.49(17) . . . . ?
C6B C1B C13 N1 -141.58(16) . . . . ?
C2B C1B C13 N1 40.6(2) . . . . ?
C2A C1A C13 O1 39.3(2) . . . . ?
C6A C1A C13 O1 -138.49(17) . . . . ?
C2A C1A C13 N1 -141.58(16) . . . . ?
C6A C1A C13 N1 40.6(2) . . . . ?
C10 C9 C14 F3B -61.6(6) . . . . ?
C8 C9 C14 F3B 118.3(6) . . . . ?
C10 C9 C14 F3A 123.3(3) . . . . ?
C8 C9 C14 F3A -56.8(4) . . . . ?
C10 C9 C14 F4A -111.0(4) . . . . ?
C8 C9 C14 F4A 68.9(4) . . . . ?
C10 C9 C14 F4B 61.8(6) . . . . ?
C8 C9 C14 F4B -118.3(6) . . . . ?
C10 C9 C14 F2A 2.4(3) . . . . ?
C8 C9 C14 F2A -177.7(3) . . . . ?
C10 C9 C14 F2B 171.7(5) . . . . ?
C8 C9 C14 F2B -8.3(6) . . . . ?

_refine_diff_density_max         0.426
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_3T1F
_database_code_depnum_ccdc_archive 'CCDC 981584'
_audit_update_record             
;
2016-03-09 deposited with the CCDC.
2016-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 F4 N O'
_chemical_formula_sum            'C14 H9 F4 N O'
_chemical_formula_weight         283.22

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_Hall  'P -2n 2a'
_symmetry_space_group_name_H-M   'P 21 c n'
_symmetry_Int_Tables_number      33

_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, -z'
'x, -y+1/2, z+1/2'
'x+1/2, y+1/2, -z+1/2'

_cell_length_a                   27.3179(14)
_cell_length_b                   5.2070(2)
_cell_length_c                   8.3017(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1180.87(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2072
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      28.11

_exptl_crystal_description       ROD
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.144
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5144
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.983
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2072
_reflns_number_gt                1876
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.953
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.996

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR 92'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2013)'
_computing_molecular_graphics    Mercury
_computing_publication_material  Mercury
_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)+(0.0521P)²+0.5451P] 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         2072
_refine_ls_number_parameters     181
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1246
_refine_ls_wR_factor_gt          0.1201
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.46289(12) -0.2941(6) 0.6051(4) 0.0311(8) Uani 1 1 d . . . . .
F2 F 0.75511(14) -0.0453(9) 0.9020(5) 0.0517(11) Uani 1 1 d . . . . .
F3 F 0.73458(13) -0.1025(8) 1.1496(5) 0.0452(10) Uani 1 1 d . . . . .
F4 F 0.73743(14) 0.2740(7) 1.0499(5) 0.0423(10) Uani 1 1 d . . . . .
N1 N 0.52574(16) -0.0598(8) 0.8211(5) 0.0196(10) Uani 1 1 d . . . . .
H1 H 0.5156 -0.2146 0.7949 0.023 Uiso 1 1 calc R U . . .
O1 O 0.50415(15) 0.3586(7) 0.8465(5) 0.0323(10) Uani 1 1 d . . . . .
C1 C 0.4419(2) 0.0697(10) 0.7644(6) 0.0204(11) Uani 1 1 d . . . . .
C2 C 0.4043(2) 0.2276(11) 0.8190(7) 0.0256(13) Uani 1 1 d . . . . .
H2 H 0.4122 0.3715 0.8844 0.031 Uiso 1 1 calc R U . . .
C3 C 0.3554(2) 0.1808(11) 0.7805(7) 0.0264(13) Uani 1 1 d . . . . .
H3 H 0.3305 0.2923 0.8189 0.032 Uiso 1 1 calc R U . . .
C4 C 0.3435(2) -0.0282(11) 0.6865(7) 0.0260(13) Uani 1 1 d . . . . .
H4 H 0.3102 -0.0634 0.6623 0.031 Uiso 1 1 calc R U . . .
C5 C 0.3799(2) -0.1871(11) 0.6272(7) 0.0265(13) Uani 1 1 d . . . . .
H5 H 0.3720 -0.3278 0.5591 0.032 Uiso 1 1 calc R U . . .
C6 C 0.4279(2) -0.1374(11) 0.6687(6) 0.0237(12) Uani 1 1 d . . . . .
C7 C 0.57472(18) -0.0313(10) 0.8705(6) 0.0173(12) Uani 1 1 d . . . . .
C8 C 0.6033(2) 0.1734(10) 0.8166(6) 0.0218(12) Uani 1 1 d . . . . .
H8 H 0.5897 0.2998 0.7474 0.026 Uiso 1 1 calc R U . . .
C9 C 0.6516(2) 0.1912(10) 0.8647(6) 0.0219(12) Uani 1 1 d . . . . .
H9 H 0.6712 0.3298 0.8275 0.026 Uiso 1 1 calc R U . . .
C10 C 0.6719(2) 0.0076(10) 0.9673(6) 0.0179(11) Uani 1 1 d . . . . .
C11 C 0.6433(2) -0.1974(10) 1.0208(7) 0.0202(12) Uani 1 1 d . . . . .
H11 H 0.6570 -0.3239 1.0900 0.024 Uiso 1 1 calc R U . . .
C12 C 0.5949(2) -0.2152(10) 0.9724(6) 0.0206(11) Uani 1 1 d . . . . .
H12 H 0.5753 -0.3541 1.0091 0.025 Uiso 1 1 calc R U . . .
C13 C 0.4935(2) 0.1355(10) 0.8113(6) 0.0217(12) Uani 1 1 d . . . . .
C14 C 0.7246(2) 0.0314(11) 1.0164(7) 0.0248(13) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C6 1.363(6) . ?
F2 C14 1.326(7) . ?
F3 C14 1.335(7) . ?
F4 C14 1.340(7) . ?
N1 C13 1.348(7) . ?
N1 C7 1.407(7) . ?
N1 H1 0.8800 . ?
O1 C13 1.233(6) . ?
C1 C2 1.392(8) . ?
C1 C6 1.394(7) . ?
C1 C13 1.500(8) . ?
C2 C3 1.396(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.378(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.380(8) . ?
C5 H5 0.9500 . ?
C7 C12 1.391(8) . ?
C7 C8 1.395(8) . ?
C8 C9 1.382(8) . ?
C8 H8 0.9500 . ?
C9 C10 1.395(8) . ?
C9 H9 0.9500 . ?
C10 C11 1.395(8) . ?
C10 C14 1.501(8) . ?
C11 C12 1.387(8) . ?
C11 H11 0.9500 . ?
C12 H12 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
C13 N1 C7 124.0(5) . . ?
C13 N1 H1 118.0 . . ?
C7 N1 H1 118.0 . . ?
C2 C1 C6 116.1(5) . . ?
C2 C1 C13 118.2(5) . . ?
C6 C1 C13 125.7(5) . . ?
C1 C2 C3 121.9(5) . . ?
C1 C2 H2 119.0 . . ?
C3 C2 H2 119.0 . . ?
C4 C3 C2 119.6(6) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.2(5) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 118.8(5) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
F1 C6 C5 117.2(5) . . ?
F1 C6 C1 119.4(5) . . ?
C5 C6 C1 123.3(5) . . ?
C12 C7 C8 119.9(5) . . ?
C12 C7 N1 118.7(5) . . ?
C8 C7 N1 121.3(5) . . ?
C9 C8 C7 119.6(5) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C10 120.6(5) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C9 119.8(5) . . ?
C11 C10 C14 120.9(5) . . ?
C9 C10 C14 119.3(5) . . ?
C12 C11 C10 119.5(5) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C7 120.5(5) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?
O1 C13 N1 122.8(5) . . ?
O1 C13 C1 119.9(5) . . ?
N1 C13 C1 117.2(5) . . ?
F2 C14 F3 107.9(5) . . ?
F2 C14 F4 105.5(5) . . ?
F3 C14 F4 105.5(5) . . ?
F2 C14 C10 112.5(5) . . ?
F3 C14 C10 112.2(5) . . ?
F4 C14 C10 112.6(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
C6 C1 C2 C3 0.2(8) . . . . ?
C13 C1 C2 C3 179.8(5) . . . . ?
C1 C2 C3 C4 0.4(9) . . . . ?
C2 C3 C4 C5 -1.6(8) . . . . ?
C3 C4 C5 C6 2.3(8) . . . . ?
C4 C5 C6 F1 -178.5(5) . . . . ?
C4 C5 C6 C1 -1.8(8) . . . . ?
C2 C1 C6 F1 177.2(5) . . . . ?
C13 C1 C6 F1 -2.4(8) . . . . ?
C2 C1 C6 C5 0.6(8) . . . . ?
C13 C1 C6 C5 -179.0(5) . . . . ?
C13 N1 C7 C12 138.6(5) . . . . ?
C13 N1 C7 C8 -42.8(7) . . . . ?
C12 C7 C8 C9 0.2(8) . . . . ?
N1 C7 C8 C9 -178.4(5) . . . . ?
C7 C8 C9 C10 -0.5(8) . . . . ?
C8 C9 C10 C11 0.6(8) . . . . ?
C8 C9 C10 C14 179.6(5) . . . . ?
C9 C10 C11 C12 -0.5(8) . . . . ?
C14 C10 C11 C12 -179.5(5) . . . . ?
C10 C11 C12 C7 0.3(8) . . . . ?
C8 C7 C12 C11 -0.2(8) . . . . ?
N1 C7 C12 C11 178.5(5) . . . . ?
C7 N1 C13 O1 -0.5(8) . . . . ?
C7 N1 C13 C1 -177.0(5) . . . . ?
C2 C1 C13 O1 -24.5(8) . . . . ?
C6 C1 C13 O1 155.1(5) . . . . ?
C2 C1 C13 N1 152.1(5) . . . . ?
C6 C1 C13 N1 -28.3(8) . . . . ?
C11 C10 C14 F2 101.1(6) . . . . ?
C9 C10 C14 F2 -77.9(6) . . . . ?
C11 C10 C14 F3 -20.8(7) . . . . ?
C9 C10 C14 F3 160.2(5) . . . . ?
C11 C10 C14 F4 -139.7(5) . . . . ?
C9 C10 C14 F4 41.3(7) . . . . ?

_refine_diff_density_max         0.228
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_1T2F
_database_code_depnum_ccdc_archive 'CCDC 981585'
_audit_update_record             
;
2016-03-09 deposited with the CCDC.
2016-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 F4 N O'
_chemical_formula_sum            'C14 H9 F4 N O'
_chemical_formula_weight         283.22

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.02180(10)
_cell_length_b                   39.7347(6)
_cell_length_c                   7.88660(10)
_cell_angle_alpha                90
_cell_angle_beta                 103.9420(10)
_cell_angle_gamma                90
_cell_volume                     2439.75(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5220
_cell_measurement_theta_min      2.05
_cell_measurement_theta_max      30.06

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.139
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28739
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -56
_diffrn_reflns_limit_k_max       56
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.050
_diffrn_reflns_theta_max         30.463
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             7341
_reflns_number_gt                5220
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR 92'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2013)'
_computing_molecular_graphics    Mercury
_computing_publication_material  Mercury
_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)+(0.0444P)²+1.0254P] 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         7341
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0541
_refine_ls_wR_factor_ref         0.1210
_refine_ls_wR_factor_gt          0.1104
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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 0.04122(17) 0.24815(3) 0.20359(15) 0.0404(3) Uani 1 1 d . . . . .
F2 F -0.07837(14) 0.04689(2) 0.34609(12) 0.0272(2) Uani 1 1 d . . . . .
F3 F 0.14902(15) 0.01932(2) 0.47157(13) 0.0297(2) Uani 1 1 d . . . . .
F4 F 0.16916(14) 0.07083(2) 0.39628(12) 0.0264(2) Uani 1 1 d . . . . .
O1 O 0.14648(15) 0.15185(3) 0.61479(14) 0.0220(2) Uani 1 1 d . . . . .
N1 N -0.06565(19) 0.11450(3) 0.51269(16) 0.0197(3) Uani 1 1 d . . . . .
H1N H -0.1543 0.1090 0.4274 0.024 Uiso 1 1 calc R U . . .
C1 C -0.0466(2) 0.16486(4) 0.34325(19) 0.0189(3) Uani 1 1 d . . . . .
C2 C 0.0225(2) 0.19715(4) 0.3473(2) 0.0225(3) Uani 1 1 d . . . . .
H2 H 0.1009 0.2054 0.4491 0.027 Uiso 1 1 calc R U . . .
C3 C -0.0258(3) 0.21682(4) 0.1999(2) 0.0264(4) Uani 1 1 d . . . . .
C4 C -0.1385(3) 0.20608(4) 0.0492(2) 0.0267(4) Uani 1 1 d . . . . .
H4 H -0.1673 0.2201 -0.0511 0.032 Uiso 1 1 calc R U . . .
C5 C -0.2086(2) 0.17423(4) 0.0481(2) 0.0254(4) Uani 1 1 d . . . . .
H5 H -0.2884 0.1665 -0.0538 0.030 Uiso 1 1 calc R U . . .
C6 C -0.1642(2) 0.15351(4) 0.1935(2) 0.0213(3) Uani 1 1 d . . . . .
H6 H -0.2134 0.1317 0.1913 0.026 Uiso 1 1 calc R U . . .
C7 C -0.0142(2) 0.09246(4) 0.65962(19) 0.0181(3) Uani 1 1 d . . . . .
C8 C -0.0349(2) 0.10263(4) 0.8217(2) 0.0229(3) Uani 1 1 d . . . . .
H8 H -0.0780 0.1245 0.8356 0.027 Uiso 1 1 calc R U . . .
C9 C 0.0075(2) 0.08094(4) 0.9631(2) 0.0254(4) Uani 1 1 d . . . . .
H9 H -0.0076 0.0879 1.0737 0.030 Uiso 1 1 calc R U . . .
C10 C 0.0715(2) 0.04924(4) 0.9437(2) 0.0253(4) Uani 1 1 d . . . . .
H10 H 0.1000 0.0344 1.0409 0.030 Uiso 1 1 calc R U . . .
C11 C 0.0941(2) 0.03912(4) 0.7828(2) 0.0228(3) Uani 1 1 d . . . . .
H11 H 0.1391 0.0174 0.7700 0.027 Uiso 1 1 calc R U . . .
C12 C 0.0512(2) 0.06062(4) 0.64011(19) 0.0183(3) Uani 1 1 d . . . . .
C13 C 0.0188(2) 0.14343(4) 0.50223(19) 0.0176(3) Uani 1 1 d . . . . .
C14 C 0.0734(2) 0.04937(4) 0.4654(2) 0.0217(3) Uani 1 1 d . . . . .
F5 F 0.63810(19) -0.00093(3) 0.78716(16) 0.0479(3) Uani 1 1 d . . . . .
F6 F 0.48205(14) 0.19820(2) 0.65902(12) 0.0290(2) Uani 1 1 d . . . . .
F7 F 0.64616(16) 0.22917(2) 0.54666(14) 0.0362(3) Uani 1 1 d . . . . .
F8 F 0.71068(14) 0.17735(3) 0.60490(12) 0.0293(2) Uani 1 1 d . . . . .
O2 O 0.58855(16) 0.09577(3) 0.37207(14) 0.0221(3) Uani 1 1 d . . . . .
N2 N 0.42488(19) 0.13356(3) 0.47317(17) 0.0204(3) Uani 1 1 d . . . . .
H2N H 0.3733 0.1385 0.5567 0.025 Uiso 1 1 calc R U . . .
C15 C 0.5272(2) 0.08431(4) 0.6473(2) 0.0200(3) Uani 1 1 d . . . . .
C16 C 0.5756(2) 0.05078(4) 0.6425(2) 0.0248(4) Uani 1 1 d . . . . .
H16 H 0.5954 0.0412 0.5388 0.030 Uiso 1 1 calc R U . . .
C17 C 0.5942(3) 0.03197(4) 0.7924(2) 0.0295(4) Uani 1 1 d . . . . .
C18 C 0.5718(3) 0.04490(5) 0.9474(2) 0.0311(4) Uani 1 1 d . . . . .
H18 H 0.5889 0.0313 1.0491 0.037 Uiso 1 1 calc R U . . .
C19 C 0.5237(2) 0.07832(5) 0.9509(2) 0.0283(4) Uani 1 1 d . . . . .
H19 H 0.5067 0.0878 1.0560 0.034 Uiso 1 1 calc R U . . .
C20 C 0.5002(2) 0.09803(4) 0.8015(2) 0.0244(4) Uani 1 1 d . . . . .
H20 H 0.4657 0.1209 0.8043 0.029 Uiso 1 1 calc R U . . .
C21 C 0.4095(2) 0.15642(4) 0.33092(19) 0.0189(3) Uani 1 1 d . . . . .
C22 C 0.3201(2) 0.14753(4) 0.1640(2) 0.0265(4) Uani 1 1 d . . . . .
H22 H 0.2741 0.1255 0.1420 0.032 Uiso 1 1 calc R U . . .
C23 C 0.2975(3) 0.17067(5) 0.0288(2) 0.0325(4) Uani 1 1 d . . . . .
H23 H 0.2365 0.1645 -0.0857 0.039 Uiso 1 1 calc R U . . .
C24 C 0.3636(3) 0.20281(5) 0.0607(2) 0.0338(4) Uani 1 1 d . . . . .
H24 H 0.3464 0.2187 -0.0318 0.041 Uiso 1 1 calc R U . . .
C25 C 0.4546(3) 0.21193(4) 0.2263(2) 0.0271(4) Uani 1 1 d . . . . .
H25 H 0.5006 0.2340 0.2474 0.033 Uiso 1 1 calc R U . . .
C26 C 0.4786(2) 0.18867(4) 0.3620(2) 0.0200(3) Uani 1 1 d . . . . .
C27 C 0.5152(2) 0.10468(4) 0.48500(19) 0.0191(3) Uani 1 1 d . . . . .
C28 C 0.5787(2) 0.19824(4) 0.5413(2) 0.0219(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
F1 C3 1.3537(19) . ?
F2 C14 1.351(2) . ?
F3 C14 1.3348(18) . ?
F4 C14 1.3479(19) . ?
O1 C13 1.2291(19) . ?
N1 C13 1.347(2) . ?
N1 C7 1.4316(19) . ?
N1 H1N 0.8800 . ?
C1 C2 1.395(2) . ?
C1 C6 1.397(2) . ?
C1 C13 1.502(2) . ?
C2 C3 1.377(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.376(3) . ?
C4 C5 1.384(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.388(2) . ?
C7 C12 1.392(2) . ?
C8 C9 1.386(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.382(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.384(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(2) . ?
C11 H11 0.9500 . ?
C12 C14 1.499(2) . ?
F5 C17 1.357(2) . ?
F6 C28 1.345(2) . ?
F7 C28 1.3395(18) . ?
F8 C28 1.344(2) . ?
O2 C27 1.2319(19) . ?
N2 C27 1.348(2) . ?
N2 C21 1.426(2) . ?
N2 H2N 0.8800 . ?
C15 C16 1.391(2) . ?
C15 C20 1.396(2) . ?
C15 C27 1.498(2) . ?
C16 C17 1.376(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.377(3) . ?
C18 C19 1.385(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.389(2) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.385(2) . ?
C21 C26 1.394(2) . ?
C22 C23 1.386(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.382(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.382(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.392(2) . ?
C25 H25 0.9500 . ?
C26 C28 1.497(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
C13 N1 C7 121.37(13) . . ?
C13 N1 H1N 119.3 . . ?
C7 N1 H1N 119.3 . . ?
C2 C1 C6 120.01(14) . . ?
C2 C1 C13 116.43(14) . . ?
C6 C1 C13 123.49(14) . . ?
C3 C2 C1 118.22(15) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
F1 C3 C4 118.60(15) . . ?
F1 C3 C2 118.29(16) . . ?
C4 C3 C2 123.11(16) . . ?
C3 C4 C5 118.07(15) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
C4 C5 C6 120.94(16) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 119.63(15) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C8 C7 C12 119.88(14) . . ?
C8 C7 N1 119.48(14) . . ?
C12 C7 N1 120.61(13) . . ?
C9 C8 C7 119.97(15) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C10 C9 C8 120.22(15) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 120.02(15) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C12 120.18(15) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C7 119.71(14) . . ?
C11 C12 C14 120.03(14) . . ?
C7 C12 C14 120.25(13) . . ?
O1 C13 N1 122.13(14) . . ?
O1 C13 C1 120.77(14) . . ?
N1 C13 C1 117.08(13) . . ?
F3 C14 F4 106.40(14) . . ?
F3 C14 F2 106.59(12) . . ?
F4 C14 F2 105.67(12) . . ?
F3 C14 C12 112.75(13) . . ?
F4 C14 C12 112.85(13) . . ?
F2 C14 C12 112.05(14) . . ?
C27 N2 C21 122.68(14) . . ?
C27 N2 H2N 118.7 . . ?
C21 N2 H2N 118.7 . . ?
C16 C15 C20 120.04(15) . . ?
C16 C15 C27 117.07(14) . . ?
C20 C15 C27 122.82(14) . . ?
C17 C16 C15 118.03(16) . . ?
C17 C16 H16 121.0 . . ?
C15 C16 H16 121.0 . . ?
F5 C17 C16 118.17(16) . . ?
F5 C17 C18 118.49(15) . . ?
C16 C17 C18 123.34(16) . . ?
C17 C18 C19 118.18(16) . . ?
C17 C18 H18 120.9 . . ?
C19 C18 H18 120.9 . . ?
C18 C19 C20 120.35(16) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C20 C15 120.04(16) . . ?
C19 C20 H20 120.0 . . ?
C15 C20 H20 120.0 . . ?
C22 C21 C26 119.64(15) . . ?
C22 C21 N2 120.83(14) . . ?
C26 C21 N2 119.47(13) . . ?
C21 C22 C23 120.26(16) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C24 C23 C22 119.96(16) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 120.41(16) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C24 C25 C26 119.75(17) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C25 C26 C21 119.97(15) . . ?
C25 C26 C28 120.05(14) . . ?
C21 C26 C28 119.97(13) . . ?
O2 C27 N2 122.48(14) . . ?
O2 C27 C15 121.27(15) . . ?
N2 C27 C15 116.22(14) . . ?
F7 C28 F8 106.18(14) . . ?
F7 C28 F6 105.97(13) . . ?
F8 C28 F6 105.95(13) . . ?
F7 C28 C26 112.57(13) . . ?
F8 C28 C26 112.99(13) . . ?
F6 C28 C26 112.62(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.3(3) . . . . ?
C13 C1 C2 C3 175.89(16) . . . . ?
C1 C2 C3 F1 -179.99(16) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
F1 C3 C4 C5 -178.80(16) . . . . ?
C2 C3 C4 C5 1.3(3) . . . . ?
C3 C4 C5 C6 -1.2(3) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C2 C1 C6 C5 1.4(3) . . . . ?
C13 C1 C6 C5 -175.53(16) . . . . ?
C13 N1 C7 C8 68.3(2) . . . . ?
C13 N1 C7 C12 -113.68(18) . . . . ?
C12 C7 C8 C9 -0.9(3) . . . . ?
N1 C7 C8 C9 177.18(16) . . . . ?
C7 C8 C9 C10 0.5(3) . . . . ?
C8 C9 C10 C11 0.2(3) . . . . ?
C9 C10 C11 C12 -0.6(3) . . . . ?
C10 C11 C12 C7 0.2(3) . . . . ?
C10 C11 C12 C14 -179.07(16) . . . . ?
C8 C7 C12 C11 0.5(2) . . . . ?
N1 C7 C12 C11 -177.49(15) . . . . ?
C8 C7 C12 C14 179.78(16) . . . . ?
N1 C7 C12 C14 1.7(2) . . . . ?
C7 N1 C13 O1 2.2(2) . . . . ?
C7 N1 C13 C1 -179.49(14) . . . . ?
C2 C1 C13 O1 -12.2(2) . . . . ?
C6 C1 C13 O1 164.85(16) . . . . ?
C2 C1 C13 N1 169.50(15) . . . . ?
C6 C1 C13 N1 -13.5(2) . . . . ?
C11 C12 C14 F3 -5.4(2) . . . . ?
C7 C12 C14 F3 175.37(15) . . . . ?
C11 C12 C14 F4 -125.99(16) . . . . ?
C7 C12 C14 F4 54.8(2) . . . . ?
C11 C12 C14 F2 114.88(17) . . . . ?
C7 C12 C14 F2 -64.36(19) . . . . ?
C20 C15 C16 C17 0.5(3) . . . . ?
C27 C15 C16 C17 177.44(16) . . . . ?
C15 C16 C17 F5 178.71(17) . . . . ?
C15 C16 C17 C18 -1.9(3) . . . . ?
F5 C17 C18 C19 -178.76(18) . . . . ?
C16 C17 C18 C19 1.8(3) . . . . ?
C17 C18 C19 C20 -0.4(3) . . . . ?
C18 C19 C20 C15 -0.8(3) . . . . ?
C16 C15 C20 C19 0.8(3) . . . . ?
C27 C15 C20 C19 -175.95(16) . . . . ?
C27 N2 C21 C22 67.1(2) . . . . ?
C27 N2 C21 C26 -115.92(17) . . . . ?
C26 C21 C22 C23 -0.8(3) . . . . ?
N2 C21 C22 C23 176.20(17) . . . . ?
C21 C22 C23 C24 -0.3(3) . . . . ?
C22 C23 C24 C25 1.0(3) . . . . ?
C23 C24 C25 C26 -0.5(3) . . . . ?
C24 C25 C26 C21 -0.6(3) . . . . ?
C24 C25 C26 C28 179.33(17) . . . . ?
C22 C21 C26 C25 1.2(3) . . . . ?
N2 C21 C26 C25 -175.80(16) . . . . ?
C22 C21 C26 C28 -178.68(16) . . . . ?
N2 C21 C26 C28 4.3(2) . . . . ?
C21 N2 C27 O2 -1.2(2) . . . . ?
C21 N2 C27 C15 176.72(14) . . . . ?
C16 C15 C27 O2 -19.7(2) . . . . ?
C20 C15 C27 O2 157.14(16) . . . . ?
C16 C15 C27 N2 162.38(15) . . . . ?
C20 C15 C27 N2 -20.8(2) . . . . ?
C25 C26 C28 F7 -4.3(2) . . . . ?
C21 C26 C28 F7 175.65(15) . . . . ?
C25 C26 C28 F8 -124.55(17) . . . . ?
C21 C26 C28 F8 55.4(2) . . . . ?
C25 C26 C28 F6 115.45(17) . . . . ?
C21 C26 C28 F6 -64.6(2) . . . . ?

_refine_diff_density_max         0.370
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_2T2F
_database_code_depnum_ccdc_archive 'CCDC 981586'
_audit_update_record             
;
2016-03-09 deposited with the CCDC.
2016-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 F4 N O'
_chemical_formula_sum            'C14 H9 F4 N O'
_chemical_formula_weight         283.22

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 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'

_cell_length_a                   7.156(3)
_cell_length_b                   7.072(3)
_cell_length_c                   23.277(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.651(6)
_cell_angle_gamma                90
_cell_volume                     1177.4(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2382
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      28.12

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.144
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3918
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.750
_diffrn_reflns_theta_max         27.829
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.847
_diffrn_reflns_point_group_measured_fraction_full 0.950
_reflns_number_total             2382
_reflns_number_gt                2182
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.822
_reflns_Friedel_fraction_max     0.766
_reflns_Friedel_fraction_full    0.903

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR 92'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2013)'
_computing_molecular_graphics    Mercury
_computing_publication_material  Mercury
_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)+(0.0661P)²+0.0797P] 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         2382
_refine_ls_number_parameters     185
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.0959
_refine_ls_wR_factor_gt          0.0944
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
F1A F 1.1554(3) 0.9801(3) -0.06656(9) 0.0246(5) Uani 0.944(4) 1 d . . P A 1
F1B F 1.245(5) 0.376(5) -0.1128(15) 0.0246(5) Uani 0.056(4) 1 d . . P A 2
F2 F 0.6798(3) 0.6022(3) 0.26951(8) 0.0259(5) Uani 1 1 d . . . . .
F3 F 0.8457(3) 0.4135(3) 0.32268(9) 0.0301(5) Uani 1 1 d . . . . .
F4 F 0.5514(2) 0.3608(3) 0.30935(8) 0.0271(5) Uani 1 1 d . . . . .
N1 N 0.9620(3) 0.3420(3) 0.08841(11) 0.0155(5) Uani 1 1 d . . . . .
H1 H 1.0488 0.2728 0.0726 0.019 Uiso 1 1 calc R U . . .
O1 O 0.8010(3) 0.6195(3) 0.08141(9) 0.0206(5) Uani 1 1 d . . . . .
C1A C 1.0284(4) 0.5574(4) 0.01069(13) 0.0154(6) Uani 0.944(4) 1 d . . P A 1
C2A C 1.0483(4) 0.7497(4) -0.00316(13) 0.0155(6) Uani 0.944(4) 1 d . . P A 1
H2A H 1.0010 0.8457 0.0210 0.019 Uiso 0.944(4) 1 calc R U P A 1
C3A C 1.1386(4) 0.7946(5) -0.05282(14) 0.0197(7) Uani 0.944(4) 1 d . . P A 1
C4A C 1.2102(4) 0.6614(5) -0.08921(14) 0.0205(7) Uani 0.944(4) 1 d . . P A 1
H4A H 1.2726 0.6978 -0.1230 0.025 Uiso 0.944(4) 1 calc R U P A 1
C5A C 1.1884(4) 0.4720(5) -0.07504(13) 0.0207(7) Uani 0.944(4) 1 d . . P A 1
H5A H 1.2349 0.3774 -0.0998 0.025 Uiso 0.944(4) 1 calc R U P A 1
C6A C 1.0996(4) 0.4187(5) -0.02521(13) 0.0170(6) Uani 0.944(4) 1 d . . P A 1
H6A H 1.0874 0.2887 -0.0157 0.020 Uiso 0.944(4) 1 calc R U P A 1
C1B C 1.0284(4) 0.5574(4) 0.01069(13) 0.0154(6) Uani 0.056(4) 1 d . . P A 2
C2B C 1.0996(4) 0.4187(5) -0.02521(13) 0.0170(6) Uani 0.056(4) 1 d . . P A 2
H2B H 1.0874 0.2887 -0.0157 0.020 Uiso 0.056(4) 1 calc R U P A 2
C3B C 1.1884(4) 0.4720(5) -0.07504(13) 0.0207(7) Uani 0.056(4) 1 d . . P A 2
C4B C 1.2102(4) 0.6614(5) -0.08921(14) 0.0205(7) Uani 0.056(4) 1 d . . P A 2
H4B H 1.2726 0.6978 -0.1230 0.025 Uiso 0.056(4) 1 calc R U P A 2
C5B C 1.1386(4) 0.7946(5) -0.05282(14) 0.0197(7) Uani 0.056(4) 1 d . . P A 2
H5B H 1.1520 0.9244 -0.0624 0.024 Uiso 0.056(4) 1 calc R U P A 2
C6B C 1.0483(4) 0.7497(4) -0.00316(13) 0.0155(6) Uani 0.056(4) 1 d . . P A 2
H6B H 1.0010 0.8457 0.0210 0.019 Uiso 0.056(4) 1 calc R U P A 2
C7 C 0.8769(4) 0.2669(4) 0.13828(13) 0.0151(6) Uani 1 1 d . . . . .
C8 C 0.8220(4) 0.3826(4) 0.18297(13) 0.0153(6) Uani 1 1 d . . . . .
H8 H 0.8344 0.5160 0.1805 0.018 Uiso 1 1 calc R U . . .
C9 C 0.7478(4) 0.2978(5) 0.23175(13) 0.0156(6) Uani 1 1 d . . . . .
C10 C 0.7285(4) 0.1030(4) 0.23600(14) 0.0194(7) Uani 1 1 d . . . . .
H10 H 0.6779 0.0480 0.2694 0.023 Uiso 1 1 calc R U . . .
C11 C 0.7841(4) -0.0106(4) 0.19084(14) 0.0196(7) Uani 1 1 d . . . . .
H11 H 0.7701 -0.1440 0.1931 0.024 Uiso 1 1 calc R U . . .
C12 C 0.8599(4) 0.0703(5) 0.14261(14) 0.0180(6) Uani 1 1 d . . . . .
H12 H 0.9006 -0.0081 0.1123 0.022 Uiso 1 1 calc R U . . .
C13 C 0.9208(4) 0.5100(4) 0.06341(13) 0.0149(6) Uani 1 1 d . . . . .
C14 C 0.7058(4) 0.4194(5) 0.28268(13) 0.0194(6) 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
F1A C3A 1.356(4) . ?
F1B C3B 1.19(4) . ?
F2 C14 1.340(4) . ?
F3 C14 1.348(4) . ?
F4 C14 1.348(4) . ?
N1 C13 1.352(4) . ?
N1 C7 1.428(4) . ?
N1 H1 0.8800 . ?
O1 C13 1.237(3) . ?
C1A C6A 1.394(4) . ?
C1A C2A 1.406(4) . ?
C1A C13 1.505(4) . ?
C2A C3A 1.377(4) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.376(5) . ?
C4A C5A 1.389(5) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.391(4) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C1B C2B 1.394(4) . ?
C1B C6B 1.406(4) . ?
C1B C13 1.505(4) . ?
C2B C3B 1.391(4) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.389(5) . ?
C4B C5B 1.376(5) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.377(4) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
C7 C8 1.389(4) . ?
C7 C12 1.400(4) . ?
C8 C9 1.401(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.388(4) . ?
C9 C14 1.502(4) . ?
C10 C11 1.390(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(5) . ?
C11 H11 0.9500 . ?
C12 H12 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
C13 N1 C7 125.7(2) . . ?
C13 N1 H1 117.1 . . ?
C7 N1 H1 117.1 . . ?
C6A C1A C2A 120.1(3) . . ?
C6A C1A C13 122.4(3) . . ?
C2A C1A C13 117.4(2) . . ?
C3A C2A C1A 117.9(3) . . ?
C3A C2A H2A 121.0 . . ?
C1A C2A H2A 121.0 . . ?
F1A C3A C4A 118.7(3) . . ?
F1A C3A C2A 117.9(3) . . ?
C4A C3A C2A 123.4(3) . . ?
C3A C4A C5A 117.9(3) . . ?
C3A C4A H4A 121.1 . . ?
C5A C4A H4A 121.1 . . ?
C4A C5A C6A 121.1(3) . . ?
C4A C5A H5A 119.4 . . ?
C6A C5A H5A 119.4 . . ?
C5A C6A C1A 119.5(3) . . ?
C5A C6A H6A 120.2 . . ?
C1A C6A H6A 120.2 . . ?
C2B C1B C6B 120.1(3) . . ?
C2B C1B C13 122.4(3) . . ?
C6B C1B C13 117.4(2) . . ?
C3B C2B C1B 119.5(3) . . ?
C3B C2B H2B 120.2 . . ?
C1B C2B H2B 120.2 . . ?
F1B C3B C4B 109.4(16) . . ?
F1B C3B C2B 129.3(16) . . ?
C4B C3B C2B 121.1(3) . . ?
C5B C4B C3B 117.9(3) . . ?
C5B C4B H4B 121.1 . . ?
C3B C4B H4B 121.1 . . ?
C4B C5B C6B 123.4(3) . . ?
C4B C5B H5B 118.3 . . ?
C6B C5B H5B 118.3 . . ?
C5B C6B C1B 117.9(3) . . ?
C5B C6B H6B 121.0 . . ?
C1B C6B H6B 121.0 . . ?
C8 C7 C12 120.2(3) . . ?
C8 C7 N1 121.8(3) . . ?
C12 C7 N1 117.9(3) . . ?
C7 C8 C9 118.5(3) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
C10 C9 C8 121.5(3) . . ?
C10 C9 C14 119.3(3) . . ?
C8 C9 C14 118.9(3) . . ?
C9 C10 C11 119.2(3) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C12 C11 C10 120.1(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C7 120.4(3) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
O1 C13 N1 123.3(3) . . ?
O1 C13 C1B 120.8(3) . . ?
N1 C13 C1B 115.9(2) . . ?
O1 C13 C1A 120.8(3) . . ?
N1 C13 C1A 115.9(2) . . ?
F2 C14 F4 107.0(2) . . ?
F2 C14 F3 106.4(3) . . ?
F4 C14 F3 105.9(2) . . ?
F2 C14 C9 113.7(3) . . ?
F4 C14 C9 111.9(3) . . ?
F3 C14 C9 111.5(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6A C1A C2A C3A 0.2(4) . . . . ?
C13 C1A C2A C3A -176.9(3) . . . . ?
C1A C2A C3A F1A 179.1(3) . . . . ?
C1A C2A C3A C4A -0.2(5) . . . . ?
F1A C3A C4A C5A -178.7(3) . . . . ?
C2A C3A C4A C5A 0.6(5) . . . . ?
C3A C4A C5A C6A -1.0(5) . . . . ?
C4A C5A C6A C1A 1.0(5) . . . . ?
C2A C1A C6A C5A -0.7(4) . . . . ?
C13 C1A C6A C5A 176.3(3) . . . . ?
C6B C1B C2B C3B -0.7(4) . . . . ?
C13 C1B C2B C3B 176.3(3) . . . . ?
C1B C2B C3B F1B -174(2) . . . . ?
C1B C2B C3B C4B 1.0(5) . . . . ?
F1B C3B C4B C5B 174.8(19) . . . . ?
C2B C3B C4B C5B -1.0(5) . . . . ?
C3B C4B C5B C6B 0.6(5) . . . . ?
C4B C5B C6B C1B -0.2(5) . . . . ?
C2B C1B C6B C5B 0.2(4) . . . . ?
C13 C1B C6B C5B -176.9(3) . . . . ?
C13 N1 C7 C8 -35.0(4) . . . . ?
C13 N1 C7 C12 148.6(3) . . . . ?
C12 C7 C8 C9 -0.7(4) . . . . ?
N1 C7 C8 C9 -176.9(3) . . . . ?
C7 C8 C9 C10 -0.1(4) . . . . ?
C7 C8 C9 C14 174.0(3) . . . . ?
C8 C9 C10 C11 0.0(5) . . . . ?
C14 C9 C10 C11 -174.0(3) . . . . ?
C9 C10 C11 C12 0.8(5) . . . . ?
C10 C11 C12 C7 -1.6(5) . . . . ?
C8 C7 C12 C11 1.5(4) . . . . ?
N1 C7 C12 C11 177.9(3) . . . . ?
C7 N1 C13 O1 -0.4(5) . . . . ?
C7 N1 C13 C1B -179.4(3) . . . . ?
C7 N1 C13 C1A -179.4(3) . . . . ?
C2B C1B C13 O1 -151.4(3) . . . . ?
C6B C1B C13 O1 25.6(4) . . . . ?
C2B C1B C13 N1 27.6(4) . . . . ?
C6B C1B C13 N1 -155.3(3) . . . . ?
C6A C1A C13 O1 -151.4(3) . . . . ?
C2A C1A C13 O1 25.6(4) . . . . ?
C6A C1A C13 N1 27.6(4) . . . . ?
C2A C1A C13 N1 -155.3(3) . . . . ?
C10 C9 C14 F2 -162.9(3) . . . . ?
C8 C9 C14 F2 22.9(4) . . . . ?
C10 C9 C14 F4 -41.6(4) . . . . ?
C8 C9 C14 F4 144.2(3) . . . . ?
C10 C9 C14 F3 76.8(3) . . . . ?
C8 C9 C14 F3 -97.4(3) . . . . ?

_refine_diff_density_max         0.297
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_1T3F
_database_code_depnum_ccdc_archive 'CCDC 981587'
_audit_update_record             
;
2016-03-09 deposited with the CCDC.
2016-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 F4 N O'
_chemical_formula_sum            'C14 H9 F4 N O'
_chemical_formula_weight         283.22

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   15.4221(4)
_cell_length_b                   7.9238(2)
_cell_length_c                   19.9518(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.9210(10)
_cell_angle_gamma                90
_cell_volume                     2437.83(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4283
_cell_measurement_theta_min      1.86
_cell_measurement_theta_max      25.00

_exptl_crystal_description       ROD
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.139
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19707
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.656
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4283
_reflns_number_gt                3343
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR 92'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2013)'
_computing_molecular_graphics    Mercury
_computing_publication_material  Mercury
_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)+(0.0944P)²+0.3527P] 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         4283
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_ref         0.1492
_refine_ls_wR_factor_gt          0.1361
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_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 0.45910(7) 0.09476(16) 0.44441(6) 0.0375(3) Uani 1 1 d . . . . .
F2 F 0.72677(7) 0.29374(15) 0.03870(5) 0.0329(3) Uani 1 1 d . . . . .
F3 F 0.67125(7) 0.09570(14) 0.09811(5) 0.0282(3) Uani 1 1 d . . . . .
F4 F 0.69409(7) 0.34074(14) 0.14121(5) 0.0297(3) Uani 1 1 d . . . . .
N1 N 0.75943(10) 0.08124(19) 0.22933(7) 0.0212(4) Uani 1 1 d . . . . .
H1 H 0.7175 0.0112 0.2178 0.025 Uiso 1 1 calc R U . . .
O1 O 0.81114(8) 0.26463(16) 0.30658(6) 0.0238(3) Uani 1 1 d . . . . .
C1 C 0.67442(12) 0.1378(2) 0.32795(9) 0.0199(4) Uani 1 1 d . . . . .
C2 C 0.67758(12) 0.1876(2) 0.39503(10) 0.0243(4) Uani 1 1 d . . . . .
H2 H 0.7297 0.2332 0.4135 0.029 Uiso 1 1 calc R U . . .
C3 C 0.60524(13) 0.1712(3) 0.43508(10) 0.0287(5) Uani 1 1 d . . . . .
H3 H 0.6075 0.2020 0.4811 0.034 Uiso 1 1 calc R U . . .
C4 C 0.53019(12) 0.1089(3) 0.40627(10) 0.0268(5) Uani 1 1 d . . . . .
C5 C 0.52437(12) 0.0598(2) 0.33996(10) 0.0259(5) Uani 1 1 d . . . . .
H5 H 0.4715 0.0179 0.3214 0.031 Uiso 1 1 calc R U . . .
C6 C 0.59758(12) 0.0733(2) 0.30128(10) 0.0223(4) Uani 1 1 d . . . . .
H6 H 0.5953 0.0379 0.2558 0.027 Uiso 1 1 calc R U . . .
C7 C 0.83052(11) 0.1015(2) 0.18546(9) 0.0208(4) Uani 1 1 d . . . . .
C8 C 0.91271(12) 0.0479(2) 0.20498(10) 0.0254(4) Uani 1 1 d . . . . .
H8 H 0.9224 0.0026 0.2486 0.030 Uiso 1 1 calc R U . . .
C9 C 0.98057(12) 0.0604(2) 0.16077(10) 0.0265(5) Uani 1 1 d . . . . .
H9 H 1.0368 0.0233 0.1741 0.032 Uiso 1 1 calc R U . . .
C10 C 0.96730(13) 0.1267(3) 0.09717(10) 0.0284(5) Uani 1 1 d . . . . .
H10 H 1.0141 0.1339 0.0670 0.034 Uiso 1 1 calc R U . . .
C11 C 0.88564(12) 0.1825(3) 0.07776(10) 0.0247(4) Uani 1 1 d . . . . .
H11 H 0.8766 0.2296 0.0344 0.030 Uiso 1 1 calc R U . . .
C12 C 0.81711(12) 0.1695(2) 0.12152(9) 0.0214(4) Uani 1 1 d . . . . .
C13 C 0.75385(11) 0.1649(2) 0.28773(9) 0.0199(4) Uani 1 1 d . . . . .
C14 C 0.72818(12) 0.2255(2) 0.10004(9) 0.0236(4) Uani 1 1 d . . . . .
F5 F -0.02348(7) -0.15998(16) 0.44974(6) 0.0380(3) Uani 1 1 d . . . . .
F6 F 0.22601(7) 0.05195(15) 0.03318(6) 0.0363(3) Uani 1 1 d . . . . .
F7 F 0.17174(7) -0.14386(14) 0.09399(6) 0.0294(3) Uani 1 1 d . . . . .
F8 F 0.19578(6) 0.10092(14) 0.13607(6) 0.0303(3) Uani 1 1 d . . . . .
N2 N 0.26380(10) -0.15628(19) 0.22423(7) 0.0207(4) Uani 1 1 d . . . . .
H2A H 0.2213 -0.2258 0.2136 0.025 Uiso 1 1 calc R U . . .
O2 O 0.31768(7) 0.02907(16) 0.30012(6) 0.0235(3) Uani 1 1 d . . . . .
C15 C 0.18341(11) -0.1002(2) 0.32534(9) 0.0205(4) Uani 1 1 d . . . . .
C16 C 0.18798(12) -0.0449(2) 0.39152(9) 0.0249(4) Uani 1 1 d . . . . .
H16 H 0.2397 0.0069 0.4079 0.030 Uiso 1 1 calc R U . . .
C17 C 0.11856(13) -0.0642(2) 0.43378(10) 0.0274(5) Uani 1 1 d . . . . .
H17 H 0.1219 -0.0267 0.4790 0.033 Uiso 1 1 calc R U . . .
C18 C 0.04460(12) -0.1389(2) 0.40867(10) 0.0254(5) Uani 1 1 d . . . . .
C19 C 0.03659(12) -0.1947(2) 0.34353(10) 0.0243(4) Uani 1 1 d . . . . .
H19 H -0.0158 -0.2449 0.3276 0.029 Uiso 1 1 calc R U . . .
C20 C 0.10684(12) -0.1756(2) 0.30177(9) 0.0224(4) Uani 1 1 d . . . . .
H20 H 0.1029 -0.2141 0.2567 0.027 Uiso 1 1 calc R U . . .
C21 C 0.33366(11) -0.1371(2) 0.17906(9) 0.0188(4) Uani 1 1 d . . . . .
C22 C 0.41659(12) -0.1875(2) 0.19756(10) 0.0242(4) Uani 1 1 d . . . . .
H22 H 0.4272 -0.2314 0.2412 0.029 Uiso 1 1 calc R U . . .
C23 C 0.48395(12) -0.1748(3) 0.15331(10) 0.0284(5) Uani 1 1 d . . . . .
H23 H 0.5407 -0.2089 0.1665 0.034 Uiso 1 1 calc R U . . .
C24 C 0.46853(12) -0.1119(3) 0.08941(10) 0.0285(5) Uani 1 1 d . . . . .
H24 H 0.5147 -0.1042 0.0586 0.034 Uiso 1 1 calc R U . . .
C25 C 0.38600(12) -0.0602(2) 0.07044(9) 0.0251(5) Uani 1 1 d . . . . .
H25 H 0.3757 -0.0163 0.0267 0.030 Uiso 1 1 calc R U . . .
C26 C 0.31849(11) -0.0722(2) 0.11489(9) 0.0200(4) Uani 1 1 d . . . . .
C27 C 0.26044(11) -0.0714(2) 0.28289(9) 0.0198(4) Uani 1 1 d . . . . .
C28 C 0.22873(12) -0.0155(2) 0.09480(9) 0.0237(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C4 1.349(2) . ?
F2 C14 1.338(2) . ?
F3 C14 1.352(2) . ?
F4 C14 1.341(2) . ?
N1 C13 1.344(2) . ?
N1 C7 1.423(2) . ?
N1 H1 0.8800 . ?
O1 C13 1.239(2) . ?
C1 C6 1.389(2) . ?
C1 C2 1.395(3) . ?
C1 C13 1.491(3) . ?
C2 C3 1.389(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.375(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(3) . ?
C5 C6 1.382(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.387(3) . ?
C7 C12 1.397(3) . ?
C8 C9 1.383(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.384(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(3) . ?
C11 H11 0.9500 . ?
C12 C14 1.497(2) . ?
F5 C18 1.353(2) . ?
F6 C28 1.341(2) . ?
F7 C28 1.344(2) . ?
F8 C28 1.342(2) . ?
N2 C27 1.351(2) . ?
N2 C21 1.424(2) . ?
N2 H2A 0.8800 . ?
O2 C27 1.234(2) . ?
C15 C16 1.392(3) . ?
C15 C20 1.398(3) . ?
C15 C27 1.488(3) . ?
C16 C17 1.382(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.373(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.376(3) . ?
C19 C20 1.386(3) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.384(3) . ?
C21 C26 1.396(3) . ?
C22 C23 1.378(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.386(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.384(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.382(3) . ?
C25 H25 0.9500 . ?
C26 C28 1.504(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
C13 N1 C7 122.57(15) . . ?
C13 N1 H1 118.7 . . ?
C7 N1 H1 118.7 . . ?
C6 C1 C2 119.21(17) . . ?
C6 C1 C13 123.38(17) . . ?
C2 C1 C13 117.34(16) . . ?
C3 C2 C1 120.62(17) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 118.13(18) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
F1 C4 C3 118.69(18) . . ?
F1 C4 C5 118.43(17) . . ?
C3 C4 C5 122.88(18) . . ?
C4 C5 C6 118.17(17) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C5 C6 C1 120.95(18) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
C8 C7 C12 119.73(17) . . ?
C8 C7 N1 120.15(17) . . ?
C12 C7 N1 120.07(16) . . ?
C9 C8 C7 119.76(18) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 120.62(18) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C9 119.84(19) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 119.99(18) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C7 120.05(17) . . ?
C11 C12 C14 120.14(16) . . ?
C7 C12 C14 119.80(16) . . ?
O1 C13 N1 121.47(17) . . ?
O1 C13 C1 121.09(16) . . ?
N1 C13 C1 117.40(15) . . ?
F2 C14 F4 106.50(15) . . ?
F2 C14 F3 106.28(14) . . ?
F4 C14 F3 105.94(14) . . ?
F2 C14 C12 112.52(15) . . ?
F4 C14 C12 113.11(15) . . ?
F3 C14 C12 111.98(15) . . ?
C27 N2 C21 122.35(15) . . ?
C27 N2 H2A 118.8 . . ?
C21 N2 H2A 118.8 . . ?
C16 C15 C20 118.89(17) . . ?
C16 C15 C27 117.60(16) . . ?
C20 C15 C27 123.49(17) . . ?
C17 C16 C15 121.08(17) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C18 C17 C16 118.19(18) . . ?
C18 C17 H17 120.9 . . ?
C16 C17 H17 120.9 . . ?
F5 C18 C17 118.73(17) . . ?
F5 C18 C19 118.28(17) . . ?
C17 C18 C19 122.99(18) . . ?
C18 C19 C20 118.27(17) . . ?
C18 C19 H19 120.9 . . ?
C20 C19 H19 120.9 . . ?
C19 C20 C15 120.57(17) . . ?
C19 C20 H20 119.7 . . ?
C15 C20 H20 119.7 . . ?
C22 C21 C26 119.43(17) . . ?
C22 C21 N2 120.38(17) . . ?
C26 C21 N2 120.16(16) . . ?
C23 C22 C21 120.72(18) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C24 119.73(17) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C25 C24 C23 120.09(18) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C26 C25 C24 120.22(18) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C21 119.80(16) . . ?
C25 C26 C28 120.56(16) . . ?
C21 C26 C28 119.64(16) . . ?
O2 C27 N2 121.68(17) . . ?
O2 C27 C15 120.98(16) . . ?
N2 C27 C15 117.32(15) . . ?
F6 C28 F8 106.39(15) . . ?
F6 C28 F7 106.25(14) . . ?
F8 C28 F7 105.88(14) . . ?
F6 C28 C26 112.24(15) . . ?
F8 C28 C26 113.45(14) . . ?
F7 C28 C26 112.09(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.8(3) . . . . ?
C13 C1 C2 C3 177.99(18) . . . . ?
C1 C2 C3 C4 -1.7(3) . . . . ?
C2 C3 C4 F1 -179.00(17) . . . . ?
C2 C3 C4 C5 1.2(3) . . . . ?
F1 C4 C5 C6 -179.48(17) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C4 C5 C6 C1 -1.3(3) . . . . ?
C2 C1 C6 C5 0.8(3) . . . . ?
C13 C1 C6 C5 -176.24(17) . . . . ?
C13 N1 C7 C8 66.4(2) . . . . ?
C13 N1 C7 C12 -116.10(19) . . . . ?
C12 C7 C8 C9 -0.7(3) . . . . ?
N1 C7 C8 C9 176.83(17) . . . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
C8 C9 C10 C11 0.6(3) . . . . ?
C9 C10 C11 C12 -1.0(3) . . . . ?
C10 C11 C12 C7 0.5(3) . . . . ?
C10 C11 C12 C14 -178.38(17) . . . . ?
C8 C7 C12 C11 0.3(3) . . . . ?
N1 C7 C12 C11 -177.21(17) . . . . ?
C8 C7 C12 C14 179.23(17) . . . . ?
N1 C7 C12 C14 1.7(3) . . . . ?
C7 N1 C13 O1 -0.2(3) . . . . ?
C7 N1 C13 C1 177.65(15) . . . . ?
C6 C1 C13 O1 158.80(17) . . . . ?
C2 C1 C13 O1 -18.3(2) . . . . ?
C6 C1 C13 N1 -19.1(3) . . . . ?
C2 C1 C13 N1 163.86(16) . . . . ?
C11 C12 C14 F2 -3.6(2) . . . . ?
C7 C12 C14 F2 177.46(16) . . . . ?
C11 C12 C14 F4 -124.35(19) . . . . ?
C7 C12 C14 F4 56.7(2) . . . . ?
C11 C12 C14 F3 116.04(19) . . . . ?
C7 C12 C14 F3 -62.9(2) . . . . ?
C20 C15 C16 C17 0.3(3) . . . . ?
C27 C15 C16 C17 178.80(17) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C16 C17 C18 F5 179.35(17) . . . . ?
C16 C17 C18 C19 -0.2(3) . . . . ?
F5 C18 C19 C20 -178.95(17) . . . . ?
C17 C18 C19 C20 0.6(3) . . . . ?
C18 C19 C20 C15 -0.6(3) . . . . ?
C16 C15 C20 C19 0.2(3) . . . . ?
C27 C15 C20 C19 -178.29(17) . . . . ?
C27 N2 C21 C22 64.8(2) . . . . ?
C27 N2 C21 C26 -117.19(19) . . . . ?
C26 C21 C22 C23 -0.2(3) . . . . ?
N2 C21 C22 C23 177.76(17) . . . . ?
C21 C22 C23 C24 -0.4(3) . . . . ?
C22 C23 C24 C25 0.8(3) . . . . ?
C23 C24 C25 C26 -0.5(3) . . . . ?
C24 C25 C26 C21 -0.2(3) . . . . ?
C24 C25 C26 C28 179.68(17) . . . . ?
C22 C21 C26 C25 0.5(3) . . . . ?
N2 C21 C26 C25 -177.45(16) . . . . ?
C22 C21 C26 C28 -179.34(17) . . . . ?
N2 C21 C26 C28 2.7(3) . . . . ?
C21 N2 C27 O2 0.8(3) . . . . ?
C21 N2 C27 C15 179.09(15) . . . . ?
C16 C15 C27 O2 -15.9(3) . . . . ?
C20 C15 C27 O2 162.60(17) . . . . ?
C16 C15 C27 N2 165.84(16) . . . . ?
C20 C15 C27 N2 -15.7(3) . . . . ?
C25 C26 C28 F6 -3.3(2) . . . . ?
C21 C26 C28 F6 176.59(16) . . . . ?
C25 C26 C28 F8 -123.93(18) . . . . ?
C21 C26 C28 F8 55.9(2) . . . . ?
C25 C26 C28 F7 116.21(19) . . . . ?
C21 C26 C28 F7 -63.9(2) . . . . ?

_refine_diff_density_max         0.560
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_3T3F
_database_code_depnum_ccdc_archive 'CCDC 981588'
_audit_update_record             
;
2016-03-09 deposited with the CCDC.
2016-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H9 F4 N O'
_chemical_formula_weight         283.22

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   12.9475(16)
_cell_length_b                   9.5928(11)
_cell_length_c                   10.0791(12)
_cell_angle_alpha                90
_cell_angle_beta                 106.428(7)
_cell_angle_gamma                90
_cell_volume                     1200.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2086
_cell_measurement_theta_min      1.86
_cell_measurement_theta_max      27.11

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.603
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.106
_exptl_absorpt_coefficient_mu    0.141
_shelx_estimated_absorpt_T_min   0.920
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10174
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.640
_diffrn_reflns_theta_max         28.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             2974
_reflns_number_gt                2282
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR 92'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2013)'
_computing_molecular_graphics    Mercury
_computing_publication_material  Mercury
_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)+(0.1357P)²+0.0381P] 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         2974
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0609
_refine_ls_wR_factor_ref         0.2121
_refine_ls_wR_factor_gt          0.1868
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.112
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.34440(15) 0.5576(2) 0.1032(2) 0.0179(4) Uani 1 1 d . . . . .
C2 C 0.40766(15) 0.4743(2) 0.2079(2) 0.0200(5) Uani 1 1 d . . . . .
H2 H 0.4189 0.5000 0.3020 0.024 Uiso 1 1 calc R U . . .
C3 C 0.45454(17) 0.3533(2) 0.1754(2) 0.0225(5) Uani 1 1 d . . . . .
H3 H 0.4981 0.2960 0.2462 0.027 Uiso 1 1 calc R U . . .
C4 C 0.43635(16) 0.3188(2) 0.0389(2) 0.0211(5) Uani 1 1 d . . . . .
C5 C 0.37416(17) 0.3977(2) -0.0671(2) 0.0225(5) Uani 1 1 d . . . . .
H5 H 0.3628 0.3702 -0.1607 0.027 Uiso 1 1 calc R U . . .
C6 C 0.32805(16) 0.5192(2) -0.0340(2) 0.0203(4) Uani 1 1 d . . . . .
H6 H 0.2851 0.5762 -0.1057 0.024 Uiso 1 1 calc R U . . .
C7 C 0.21094(15) 0.9128(2) 0.0597(2) 0.0178(4) Uani 1 1 d . . . . .
C8 C 0.14216(15) 0.9266(2) 0.1435(2) 0.0194(5) Uani 1 1 d . . . . .
H8 H 0.1290 0.8491 0.1952 0.023 Uiso 1 1 calc R U . . .
C9 C 0.09300(16) 1.0542(2) 0.1511(2) 0.0214(5) Uani 1 1 d . . . . .
H9 H 0.0464 1.0641 0.2083 0.026 Uiso 1 1 calc R U . . .
C10 C 0.11187(16) 1.1667(2) 0.0754(2) 0.0204(5) Uani 1 1 d . . . . .
C11 C 0.17849(17) 1.1530(2) -0.0106(2) 0.0253(5) Uani 1 1 d . . . . .
H11 H 0.1900 1.2300 -0.0640 0.030 Uiso 1 1 calc R U . . .
C12 C 0.22801(17) 1.0258(2) -0.0175(2) 0.0264(5) Uani 1 1 d . . . . .
H12 H 0.2739 1.0161 -0.0757 0.032 Uiso 1 1 calc R U . . .
C13 C 0.29361(15) 0.6855(2) 0.1446(2) 0.0172(4) Uani 1 1 d . . . . .
C14 C 0.06072(17) 1.3063(2) 0.0806(2) 0.0233(5) Uani 1 1 d . . . . .
N1 N 0.26217(13) 0.78558(17) 0.04603(18) 0.0189(4) Uani 1 1 d . . . . .
H1 H 0.2749 0.7697 -0.0339 0.023 Uiso 1 1 calc R U . . .
O1 O 0.28447(11) 0.69758(15) 0.26225(15) 0.0219(4) Uani 1 1 d . . . . .
F1 F 0.48210(10) 0.20013(13) 0.00688(14) 0.0293(4) Uani 1 1 d . . . . .
F2 F 0.01548(13) 1.35795(15) -0.04518(15) 0.0422(4) Uani 1 1 d . . . . .
F3 F -0.01698(12) 1.30185(15) 0.14422(17) 0.0405(4) Uani 1 1 d . . . . .
F4 F 0.13184(11) 1.40126(14) 0.14828(17) 0.0396(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
C1 C6 1.388(3) . ?
C1 C2 1.391(3) . ?
C1 C13 1.505(3) . ?
C2 C3 1.391(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.369(3) . ?
C3 H3 0.9500 . ?
C4 F1 1.364(2) . ?
C4 C5 1.370(3) . ?
C5 C6 1.393(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.388(3) . ?
C7 C8 1.397(2) . ?
C7 N1 1.415(2) . ?
C8 C9 1.392(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.382(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.391(2) . ?
C10 C14 1.502(3) . ?
C11 C12 1.390(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 O1 1.230(2) . ?
C13 N1 1.358(3) . ?
C14 F2 1.333(3) . ?
C14 F4 1.337(3) . ?
C14 F3 1.338(2) . ?
N1 H1 0.8800 . ?

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
C6 C1 C2 119.64(18) . . ?
C6 C1 C13 122.43(19) . . ?
C2 C1 C13 117.91(18) . . ?
C3 C2 C1 120.20(19) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 118.4(2) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
F1 C4 C3 118.49(19) . . ?
F1 C4 C5 118.35(19) . . ?
C3 C4 C5 123.15(19) . . ?
C4 C5 C6 118.2(2) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C1 C6 C5 120.4(2) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C12 C7 C8 119.71(18) . . ?
C12 C7 N1 117.77(16) . . ?
C8 C7 N1 122.49(17) . . ?
C9 C8 C7 119.71(18) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C10 C9 C8 120.10(17) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 120.52(18) . . ?
C9 C10 C14 121.89(17) . . ?
C11 C10 C14 117.59(18) . . ?
C12 C11 C10 119.38(19) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C7 C12 C11 120.55(17) . . ?
C7 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
O1 C13 N1 123.21(17) . . ?
O1 C13 C1 120.80(18) . . ?
N1 C13 C1 115.96(17) . . ?
F2 C14 F4 106.62(18) . . ?
F2 C14 F3 106.26(17) . . ?
F4 C14 F3 106.26(17) . . ?
F2 C14 C10 112.19(18) . . ?
F4 C14 C10 112.25(18) . . ?
F3 C14 C10 112.77(17) . . ?
C13 N1 C7 126.21(16) . . ?
C13 N1 H1 116.9 . . ?
C7 N1 H1 116.9 . . ?

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
C6 C1 C2 C3 0.2(3) . . . . ?
C13 C1 C2 C3 178.63(16) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C3 C4 F1 -179.88(16) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
F1 C4 C5 C6 -179.67(16) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
C13 C1 C6 C5 -178.09(17) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C12 C7 C8 C9 -1.3(3) . . . . ?
N1 C7 C8 C9 -179.10(19) . . . . ?
C7 C8 C9 C10 0.3(3) . . . . ?
C8 C9 C10 C11 1.1(3) . . . . ?
C8 C9 C10 C14 -179.9(2) . . . . ?
C9 C10 C11 C12 -1.4(3) . . . . ?
C14 C10 C11 C12 179.5(2) . . . . ?
C8 C7 C12 C11 0.9(3) . . . . ?
N1 C7 C12 C11 178.9(2) . . . . ?
C10 C11 C12 C7 0.4(4) . . . . ?
C6 C1 C13 O1 160.06(19) . . . . ?
C2 C1 C13 O1 -18.3(3) . . . . ?
C6 C1 C13 N1 -21.6(3) . . . . ?
C2 C1 C13 N1 159.97(18) . . . . ?
C9 C10 C14 F2 -131.1(2) . . . . ?
C11 C10 C14 F2 48.0(3) . . . . ?
C9 C10 C14 F4 108.8(2) . . . . ?
C11 C10 C14 F4 -72.1(3) . . . . ?
C9 C10 C14 F3 -11.2(3) . . . . ?
C11 C10 C14 F3 167.93(19) . . . . ?
O1 C13 N1 C7 -3.1(3) . . . . ?
C1 C13 N1 C7 178.66(17) . . . . ?
C12 C7 N1 C13 151.0(2) . . . . ?
C8 C7 N1 C13 -31.2(3) . . . . ?

_refine_diff_density_max         0.451
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.089

####################################################################### 
# 
# 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_1F1T
_database_code_depnum_ccdc_archive 'CCDC 981589'
_audit_update_record             
;
2016-03-09 deposited with the CCDC.
2016-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 F4 N O'
_chemical_formula_sum            'C14 H9 F4 N O'
_chemical_formula_weight         283.22

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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'

_cell_length_a                   8.9068(13)
_cell_length_b                   14.315(2)
_cell_length_c                   9.8311(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1253.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2451
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      28.21

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.136
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7120
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.513
_diffrn_reflns_theta_max         28.206
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.795
_diffrn_reflns_point_group_measured_fraction_full 0.863
_reflns_number_total             2451
_reflns_number_gt                2426
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.572
_reflns_Friedel_fraction_max     0.614
_reflns_Friedel_fraction_full    0.707

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR 92'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2013)'
_computing_molecular_graphics    Mercury
_computing_publication_material  Mercury
_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)+(0.0391P)²+0.3276P] 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         2451
_refine_ls_number_parameters     185
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0763
_refine_ls_wR_factor_gt          0.0759
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.095
_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
F1A F 0.21166(17) 0.29497(9) 0.55136(18) 0.0292(4) Uani 0.873(3) 1 d . . P A 1
F1B F -0.0382(12) 0.0512(6) 0.3400(12) 0.0292(4) Uani 0.127(3) 1 d . . P A 2
F2 F 0.05240(17) 0.27065(10) -0.16067(16) 0.0381(3) Uani 1 1 d . . . . .
F3 F 0.09826(14) 0.20422(8) 0.03117(16) 0.0301(3) Uani 1 1 d . . . . .
F4 F 0.24379(15) 0.31292(10) -0.04278(19) 0.0374(4) Uani 1 1 d . . . . .
N1 N 0.00614(17) 0.24037(11) 0.34992(19) 0.0191(3) Uani 1 1 d . . . . .
H1 H -0.0926 0.2405 0.3465 0.023 Uiso 1 1 calc R U . A 1
O1 O 0.21795(16) 0.31211(11) 0.27021(18) 0.0260(3) Uani 1 1 d . . . . .
C1 C -0.0151(2) 0.35996(13) 0.1784(2) 0.0176(4) Uani 1 1 d . . . . .
C2 C 0.0026(2) 0.35897(12) 0.0371(2) 0.0191(4) Uani 1 1 d . . . . .
C3 C -0.0723(2) 0.42393(13) -0.0428(2) 0.0209(4) Uani 1 1 d . . . . .
H3 H -0.0597 0.4234 -0.1388 0.025 Uiso 1 1 calc R U . . .
C4 C -0.1659(2) 0.48996(13) 0.0175(2) 0.0251(5) Uani 1 1 d . . . . .
H4 H -0.2142 0.5358 -0.0370 0.030 Uiso 1 1 calc R U . . .
C5 C -0.1885(2) 0.48871(14) 0.1562(2) 0.0240(5) Uani 1 1 d . . . . .
H5 H -0.2551 0.5325 0.1966 0.029 Uiso 1 1 calc R U . . .
C6 C -0.1145(2) 0.42394(13) 0.2375(2) 0.0204(4) Uani 1 1 d . . . . .
H6 H -0.1314 0.4231 0.3329 0.024 Uiso 1 1 calc R U . . .
C7A C 0.07795(19) 0.17628(13) 0.4390(2) 0.0187(4) Uani 0.873(3) 1 d . . P A 1
C8A C 0.1803(2) 0.20398(13) 0.5367(2) 0.0222(4) Uani 0.873(3) 1 d . . P A 1
C9A C 0.2504(2) 0.14107(15) 0.6225(3) 0.0281(4) Uani 0.873(3) 1 d . . P A 1
H9A H 0.3221 0.1619 0.6874 0.034 Uiso 0.873(3) 1 calc R U P A 1
C10A C 0.2141(2) 0.04672(15) 0.6123(3) 0.0295(5) Uani 0.873(3) 1 d . . P A 1
H10A H 0.2618 0.0026 0.6700 0.035 Uiso 0.873(3) 1 calc R U P A 1
C11A C 0.1088(2) 0.01707(14) 0.5182(3) 0.0281(5) Uani 0.873(3) 1 d . . P A 1
H11A H 0.0819 -0.0471 0.5134 0.034 Uiso 0.873(3) 1 calc R U P A 1
C12A C 0.0424(2) 0.08129(13) 0.4306(2) 0.0232(4) Uani 0.873(3) 1 d . . P A 1
H12A H -0.0278 0.0604 0.3645 0.028 Uiso 0.873(3) 1 calc R U P A 1
C7B C 0.07795(19) 0.17628(13) 0.4390(2) 0.0187(4) Uani 0.127(3) 1 d . . P A 2
C8B C 0.0424(2) 0.08129(13) 0.4306(2) 0.0232(4) Uani 0.127(3) 1 d . . P A 2
C9B C 0.1088(2) 0.01707(14) 0.5182(3) 0.0281(5) Uani 0.127(3) 1 d . . P A 2
H9B H 0.0819 -0.0471 0.5134 0.034 Uiso 0.127(3) 1 calc R U P A 2
C10B C 0.2141(2) 0.04672(15) 0.6123(3) 0.0295(5) Uani 0.127(3) 1 d . . P A 2
H10B H 0.2618 0.0026 0.6700 0.035 Uiso 0.127(3) 1 calc R U P A 2
C11B C 0.2504(2) 0.14107(15) 0.6225(3) 0.0281(4) Uani 0.127(3) 1 d . . P A 2
H11B H 0.3221 0.1619 0.6874 0.034 Uiso 0.127(3) 1 calc R U P A 2
C12B C 0.1803(2) 0.20398(13) 0.5367(2) 0.0222(4) Uani 0.127(3) 1 d . . P A 2
H12B H 0.2034 0.2685 0.5451 0.027 Uiso 0.127(3) 1 calc R U P A 2
C13 C 0.0815(2) 0.30098(13) 0.2705(2) 0.0189(4) Uani 1 1 d . . . . .
C14 C 0.0996(2) 0.28682(14) -0.0330(2) 0.0241(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
F1A C8A 1.340(2) . ?
F1B C8B 1.223(10) . ?
F2 C14 1.344(3) . ?
F3 C14 1.340(2) . ?
F4 C14 1.341(2) . ?
N1 C13 1.346(3) . ?
N1 C7A 1.421(3) . ?
N1 C7B 1.421(3) . ?
N1 H1 0.8800 . ?
O1 C13 1.226(2) . ?
C1 C2 1.398(3) . ?
C1 C6 1.400(3) . ?
C1 C13 1.507(3) . ?
C2 C3 1.388(3) . ?
C2 C14 1.513(3) . ?
C3 C4 1.393(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7A C8A 1.382(3) . ?
C7A C12A 1.399(3) . ?
C8A C9A 1.383(3) . ?
C9A C10A 1.392(3) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.384(4) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.391(3) . ?
C11A H11A 0.9500 . ?
C12A H12A 0.9500 . ?
C7B C12B 1.382(3) . ?
C7B C8B 1.399(3) . ?
C8B C9B 1.391(3) . ?
C9B C10B 1.384(4) . ?
C9B H9B 0.9500 . ?
C10B C11B 1.392(3) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.383(3) . ?
C11B H11B 0.9500 . ?
C12B H12B 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
C13 N1 C7A 123.33(15) . . ?
C13 N1 C7B 123.33(15) . . ?
C13 N1 H1 118.3 . . ?
C7A N1 H1 118.3 . . ?
C2 C1 C6 119.33(18) . . ?
C2 C1 C13 121.82(18) . . ?
C6 C1 C13 118.55(19) . . ?
C3 C2 C1 120.10(18) . . ?
C3 C2 C14 118.32(19) . . ?
C1 C2 C14 121.57(18) . . ?
C2 C3 C4 120.1(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 119.97(19) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.5(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 119.9(2) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C8A C7A C12A 117.98(18) . . ?
C8A C7A N1 122.68(17) . . ?
C12A C7A N1 119.32(18) . . ?
F1A C8A C7A 119.42(18) . . ?
F1A C8A C9A 118.23(19) . . ?
C7A C8A C9A 122.34(18) . . ?
C8A C9A C10A 118.8(2) . . ?
C8A C9A H9A 120.6 . . ?
C10A C9A H9A 120.6 . . ?
C11A C10A C9A 120.2(2) . . ?
C11A C10A H10A 119.9 . . ?
C9A C10A H10A 119.9 . . ?
C10A C11A C12A 119.93(19) . . ?
C10A C11A H11A 120.0 . . ?
C12A C11A H11A 120.0 . . ?
C11A C12A C7A 120.6(2) . . ?
C11A C12A H12A 119.7 . . ?
C7A C12A H12A 119.7 . . ?
C12B C7B C8B 117.98(18) . . ?
C12B C7B N1 122.68(17) . . ?
C8B C7B N1 119.32(18) . . ?
F1B C8B C9B 117.9(5) . . ?
F1B C8B C7B 121.2(5) . . ?
C9B C8B C7B 120.6(2) . . ?
C10B C9B C8B 119.93(19) . . ?
C10B C9B H9B 120.0 . . ?
C8B C9B H9B 120.0 . . ?
C9B C10B C11B 120.2(2) . . ?
C9B C10B H10B 119.9 . . ?
C11B C10B H10B 119.9 . . ?
C12B C11B C10B 118.8(2) . . ?
C12B C11B H11B 120.6 . . ?
C10B C11B H11B 120.6 . . ?
C7B C12B C11B 122.34(18) . . ?
C7B C12B H12B 118.8 . . ?
C11B C12B H12B 118.8 . . ?
O1 C13 N1 125.41(19) . . ?
O1 C13 C1 119.41(18) . . ?
N1 C13 C1 115.17(16) . . ?
F3 C14 F4 106.77(17) . . ?
F3 C14 F2 106.54(17) . . ?
F4 C14 F2 106.29(18) . . ?
F3 C14 C2 112.52(18) . . ?
F4 C14 C2 112.94(17) . . ?
F2 C14 C2 111.34(18) . . ?

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
C6 C1 C2 C3 3.2(3) . . . . ?
C13 C1 C2 C3 -170.44(16) . . . . ?
C6 C1 C2 C14 -175.45(17) . . . . ?
C13 C1 C2 C14 10.9(3) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C14 C2 C3 C4 178.30(17) . . . . ?
C2 C3 C4 C5 -2.3(3) . . . . ?
C3 C4 C5 C6 2.2(3) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C2 C1 C6 C5 -3.3(3) . . . . ?
C13 C1 C6 C5 170.50(17) . . . . ?
C13 N1 C7A C8A 54.6(3) . . . . ?
C13 N1 C7A C12A -126.8(2) . . . . ?
C12A C7A C8A F1A -177.02(18) . . . . ?
N1 C7A C8A F1A 1.6(3) . . . . ?
C12A C7A C8A C9A 1.7(3) . . . . ?
N1 C7A C8A C9A -179.6(2) . . . . ?
F1A C8A C9A C10A 177.3(2) . . . . ?
C7A C8A C9A C10A -1.4(4) . . . . ?
C8A C9A C10A C11A -0.5(4) . . . . ?
C9A C10A C11A C12A 2.0(4) . . . . ?
C10A C11A C12A C7A -1.7(3) . . . . ?
C8A C7A C12A C11A -0.1(3) . . . . ?
N1 C7A C12A C11A -178.82(19) . . . . ?
C13 N1 C7B C12B 54.6(3) . . . . ?
C13 N1 C7B C8B -126.8(2) . . . . ?
C12B C7B C8B F1B -174.3(7) . . . . ?
N1 C7B C8B F1B 7.0(7) . . . . ?
C12B C7B C8B C9B -0.1(3) . . . . ?
N1 C7B C8B C9B -178.82(19) . . . . ?
F1B C8B C9B C10B 172.6(7) . . . . ?
C7B C8B C9B C10B -1.7(3) . . . . ?
C8B C9B C10B C11B 2.0(4) . . . . ?
C9B C10B C11B C12B -0.5(4) . . . . ?
C8B C7B C12B C11B 1.7(3) . . . . ?
N1 C7B C12B C11B -179.6(2) . . . . ?
C10B C11B C12B C7B -1.4(4) . . . . ?
C7A N1 C13 O1 -4.2(3) . . . . ?
C7B N1 C13 O1 -4.2(3) . . . . ?
C7A N1 C13 C1 177.24(18) . . . . ?
C7B N1 C13 C1 177.24(18) . . . . ?
C2 C1 C13 O1 59.9(3) . . . . ?
C6 C1 C13 O1 -113.8(2) . . . . ?
C2 C1 C13 N1 -121.5(2) . . . . ?
C6 C1 C13 N1 64.9(2) . . . . ?
C3 C2 C14 F3 -145.64(18) . . . . ?
C1 C2 C14 F3 33.0(3) . . . . ?
C3 C2 C14 F4 93.4(2) . . . . ?
C1 C2 C14 F4 -88.0(2) . . . . ?
C3 C2 C14 F2 -26.1(2) . . . . ?
C1 C2 C14 F2 152.53(17) . . . . ?

_refine_diff_density_max         0.259
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_2F1T
_database_code_depnum_ccdc_archive 'CCDC 981590'
_audit_update_record             
;
2016-03-09 deposited with the CCDC.
2016-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 F4 N O'
_chemical_formula_sum            'C14 H9 F4 N O'
_chemical_formula_weight         283.22

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   11.0809(3)
_cell_length_b                   21.8822(5)
_cell_length_c                   15.3792(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.2810(10)
_cell_angle_gamma                90
_cell_volume                     3729.02(16)
_cell_formula_units_Z            12
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6524
_cell_measurement_theta_min      1.62
_cell_measurement_theta_max      25.00

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_F_000             1728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.137
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            69240
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.618
_diffrn_reflns_theta_max         30.611
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             11225
_reflns_number_gt                8192
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR 92'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2013)'
_computing_molecular_graphics    Mercury
_computing_publication_material  Mercury
_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)+(0.0431P)²+0.8903P] 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         11225
_refine_ls_number_parameters     565
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1077
_refine_ls_wR_factor_gt          0.0981
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
F1A F 0.15132(14) 0.48407(7) 0.53024(9) 0.0578(4) Uani 0.6729(17) 1 d . . P A 1
F1B F -0.1078(3) 0.33969(14) 0.56609(19) 0.0578(4) Uani 0.3271(17) 1 d . . P A
2
F2 F 0.12415(9) 0.12290(4) 0.25920(6) 0.0476(2) Uani 1 1 d . . . . .
F3 F 0.24864(8) 0.17694(4) 0.33434(5) 0.0441(2) Uani 1 1 d . . . . .
F4 F 0.31429(10) 0.11191(4) 0.24141(6) 0.0605(3) Uani 1 1 d . . . . .
N1 N 0.15112(10) 0.32537(5) 0.32427(6) 0.0266(2) Uani 1 1 d . . . . .
H1 H 0.2141 0.3440 0.3018 0.032 Uiso 1 1 calc R U . A 1
O1 O 0.02458(8) 0.24419(4) 0.30439(6) 0.03034(19) Uani 1 1 d . . . . .
C1 C 0.17848(11) 0.26002(5) 0.19971(8) 0.0247(2) Uani 1 1 d . . . . .
C2 C 0.22863(12) 0.20201(6) 0.18571(8) 0.0287(3) Uani 1 1 d . . . . .
C3 C 0.28321(12) 0.18891(6) 0.10671(9) 0.0328(3) Uani 1 1 d . . . . .
H3 H 0.3182 0.1498 0.0975 0.039 Uiso 1 1 calc R U . . .
C4 C 0.28701(13) 0.23240(6) 0.04131(9) 0.0348(3) Uani 1 1 d . . . . .
H4 H 0.3238 0.2229 -0.0127 0.042 Uiso 1 1 calc R U . . .
C5 C 0.23761(13) 0.28937(6) 0.05440(8) 0.0322(3) Uani 1 1 d . . . . .
H5 H 0.2399 0.3191 0.0094 0.039 Uiso 1 1 calc R U . . .
C6 C 0.18447(12) 0.30325(6) 0.13365(8) 0.0284(3) Uani 1 1 d . . . . .
H6 H 0.1518 0.3428 0.1428 0.034 Uiso 1 1 calc R U . . .
C7A C 0.10334(12) 0.35140(6) 0.40126(8) 0.0293(3) Uani 0.6729(17) 1 d . . P A 1
C8A C 0.01285(14) 0.32429(7) 0.44976(9) 0.0374(3) Uani 0.6729(17) 1 d . . P A 1
H8A H -0.0211 0.2863 0.4326 0.045 Uiso 0.6729(17) 1 calc R U P A 1
C9A C -0.02674(16) 0.35383(9) 0.52361(10) 0.0509(4) Uani 0.6729(17) 1 d . . P A
1
H9A H -0.0891 0.3354 0.5567 0.061 Uiso 0.6729(17) 1 calc R U P A 1
C10A C 0.01977(17) 0.40852(9) 0.55128(10) 0.0532(4) Uani 0.6729(17) 1 d . . P A
1
H10A H -0.0090 0.4281 0.6022 0.064 Uiso 0.6729(17) 1 calc R U P A 1
C11A C 0.10953(16) 0.43352(8) 0.50211(10) 0.0496(4) Uani 0.6729(17) 1 d . . P A
1
C12A C 0.15315(13) 0.40668(6) 0.42718(9) 0.0354(3) Uani 0.6729(17) 1 d . . P A
1
H12A H 0.2154 0.4255 0.3944 0.042 Uiso 0.6729(17) 1 calc R U P A 1
C7B C 0.10334(12) 0.35140(6) 0.40126(8) 0.0293(3) Uani 0.3271(17) 1 d . . P A 2
C8B C 0.01285(14) 0.32429(7) 0.44976(9) 0.0374(3) Uani 0.3271(17) 1 d . . P A 2
H8B H -0.0211 0.2863 0.4326 0.045 Uiso 0.3271(17) 1 calc R U P A 2
C9B C -0.02674(16) 0.35383(9) 0.52361(10) 0.0509(4) Uani 0.3271(17) 1 d . . P A
2
C10B C 0.01977(17) 0.40852(9) 0.55128(10) 0.0532(4) Uani 0.3271(17) 1 d . . P A
2
H10B H -0.0090 0.4281 0.6022 0.064 Uiso 0.3271(17) 1 calc R U P A 2
C11B C 0.10953(16) 0.43352(8) 0.50211(10) 0.0496(4) Uani 0.3271(17) 1 d . . P A
2
H11B H 0.1437 0.4713 0.5203 0.060 Uiso 0.3271(17) 1 calc R U P A 2
C12B C 0.15315(13) 0.40668(6) 0.42718(9) 0.0354(3) Uani 0.3271(17) 1 d . . P A
2
H12B H 0.2154 0.4255 0.3944 0.042 Uiso 0.3271(17) 1 calc R U P A 2
C13 C 0.11122(11) 0.27544(5) 0.28152(8) 0.0251(2) Uani 1 1 d . . . . .
C14 C 0.22822(14) 0.15376(6) 0.25484(9) 0.0372(3) Uani 1 1 d . . . . .
F5A F 0.17498(10) 0.00438(5) 0.50464(8) 0.0427(4) Uani 0.749(3) 1 d . . P B 1
F5B F 0.5136(3) 0.07349(18) 0.3568(2) 0.0478(12) Uani 0.251(3) 1 d . . P B 2
F6 F 0.56922(8) 0.03707(4) 0.81366(6) 0.0448(2) Uani 1 1 d . . . . .
F7 F 0.64636(9) 0.05280(5) 0.94016(6) 0.0564(3) Uani 1 1 d . . . . .
F8 F 0.45410(9) 0.04818(4) 0.92469(6) 0.0507(2) Uani 1 1 d . . . . .
N2 N 0.47645(10) 0.12202(4) 0.65279(6) 0.0257(2) Uani 1 1 d . . . . .
H2 H 0.5436 0.1427 0.6449 0.031 Uiso 1 1 calc R U . B 1
O2 O 0.33854(8) 0.09590(4) 0.75621(6) 0.02877(19) Uani 1 1 d . . . . .
C15 C 0.49799(11) 0.16174(6) 0.79830(8) 0.0265(2) Uani 1 1 d . . . . .
C16 C 0.55228(12) 0.13663(6) 0.87250(8) 0.0311(3) Uani 1 1 d . . . . .
C17 C 0.60606(13) 0.17491(7) 0.93324(9) 0.0384(3) Uani 1 1 d . . . . .
H17 H 0.6449 0.1579 0.9828 0.046 Uiso 1 1 calc R U . . .
C18 C 0.60365(14) 0.23759(7) 0.92234(9) 0.0407(3) Uani 1 1 d . . . . .
H18 H 0.6394 0.2634 0.9649 0.049 Uiso 1 1 calc R U . . .
C19 C 0.54958(14) 0.26263(6) 0.84992(9) 0.0368(3) Uani 1 1 d . . . . .
H19 H 0.5475 0.3057 0.8427 0.044 Uiso 1 1 calc R U . . .
C20 C 0.49800(12) 0.22478(6) 0.78740(8) 0.0303(3) Uani 1 1 d . . . . .
H20 H 0.4624 0.2422 0.7368 0.036 Uiso 1 1 calc R U . . .
C21A C 0.42879(11) 0.09149(5) 0.57899(8) 0.0252(2) Uani 0.749(3) 1 d . . P B 1
C22A C 0.32120(12) 0.05878(5) 0.58015(8) 0.0285(3) Uani 0.749(3) 1 d . . P B 1
H22A H 0.2760 0.0546 0.6321 0.034 Uiso 0.749(3) 1 calc R U P B 1
C23A C 0.28223(13) 0.03261(6) 0.50334(9) 0.0327(3) Uani 0.749(3) 1 d . . P B 1
C24A C 0.34444(13) 0.03608(6) 0.42664(9) 0.0346(3) Uani 0.749(3) 1 d . . P B 1
H24A H 0.3151 0.0172 0.3751 0.042 Uiso 0.749(3) 1 calc R U P B 1
C25A C 0.45182(14) 0.06825(6) 0.42777(9) 0.0346(3) Uani 0.749(3) 1 d . . P B 1
H25A H 0.4975 0.0712 0.3758 0.042 Uiso 0.749(3) 1 calc R U P B 1
C26A C 0.49444(12) 0.09616(6) 0.50232(8) 0.0301(3) Uani 0.749(3) 1 d . . P B 1
H26A H 0.5680 0.1184 0.5013 0.036 Uiso 0.749(3) 1 calc R U P B 1
C21B C 0.42879(11) 0.09149(5) 0.57899(8) 0.0252(2) Uani 0.251(3) 1 d . . P B 2
C22B C 0.32120(12) 0.05878(5) 0.58015(8) 0.0285(3) Uani 0.251(3) 1 d . . P B 2
H22B H 0.2760 0.0546 0.6321 0.034 Uiso 0.251(3) 1 calc R U P B 2
C23B C 0.28223(13) 0.03261(6) 0.50334(9) 0.0327(3) Uani 0.251(3) 1 d . . P B 2
H23B H 0.2080 0.0109 0.5036 0.039 Uiso 0.251(3) 1 calc R U P B 2
C24B C 0.34444(13) 0.03608(6) 0.42664(9) 0.0346(3) Uani 0.251(3) 1 d . . P B 2
H24B H 0.3151 0.0172 0.3751 0.042 Uiso 0.251(3) 1 calc R U P B 2
C25B C 0.45182(14) 0.06825(6) 0.42777(9) 0.0346(3) Uani 0.251(3) 1 d . . P B 2
C26B C 0.49444(12) 0.09616(6) 0.50232(8) 0.0301(3) Uani 0.251(3) 1 d . . P B 2
H26B H 0.5680 0.1184 0.5013 0.036 Uiso 0.251(3) 1 calc R U P B 2
C27 C 0.43061(11) 0.12288(5) 0.73353(8) 0.0251(2) Uani 1 1 d . . . . .
C28 C 0.55515(14) 0.06882(7) 0.88758(10) 0.0393(3) Uani 1 1 d . . . . .
F9A F 0.83703(15) 0.45863(6) 0.81406(11) 0.0461(5) Uani 0.563(2) 1 d . . P C 1
F9B F 0.51997(17) 0.41120(8) 0.61666(12) 0.0376(6) Uani 0.437(2) 1 d . . P C 2
F10 F 0.79292(8) 0.12618(4) 0.48449(5) 0.03818(19) Uani 1 1 d . . . . .
F11 F 0.98479(8) 0.11348(4) 0.48540(5) 0.0471(2) Uani 1 1 d . . . . .
F12 F 0.90899(8) 0.19944(4) 0.52511(5) 0.0411(2) Uani 1 1 d . . . . .
N3 N 0.80310(10) 0.25806(4) 0.71016(7) 0.0258(2) Uani 1 1 d . . . . .
H3A H 0.8685 0.2528 0.7419 0.031 Uiso 1 1 calc R U . C 1
O3 O 0.67352(8) 0.20663(4) 0.61983(5) 0.02750(18) Uani 1 1 d . . . . .
C29 C 0.83352(11) 0.15100(5) 0.68664(8) 0.0247(2) Uani 1 1 d . . . . .
C30 C 0.88931(11) 0.11653(5) 0.62185(8) 0.0266(2) Uani 1 1 d . . . . .
C31 C 0.94491(13) 0.06146(6) 0.64316(9) 0.0344(3) Uani 1 1 d . . . . .
H31 H 0.9847 0.0384 0.5994 0.041 Uiso 1 1 calc R U . . .
C32 C 0.94244(14) 0.04012(6) 0.72792(10) 0.0394(3) Uani 1 1 d . . . . .
H32 H 0.9781 0.0018 0.7417 0.047 Uiso 1 1 calc R U . . .
C33 C 0.88869(14) 0.07404(6) 0.79214(9) 0.0372(3) Uani 1 1 d . . . . .
H33 H 0.8878 0.0594 0.8503 0.045 Uiso 1 1 calc R U . . .
C34 C 0.83574(12) 0.12965(6) 0.77190(8) 0.0303(3) Uani 1 1 d . . . . .
H34 H 0.8005 0.1535 0.8167 0.036 Uiso 1 1 calc R U . . .
C35A C 0.75429(12) 0.31788(5) 0.71072(8) 0.0265(2) Uani 0.563(2) 1 d . . P C 1
C36A C 0.65304(12) 0.33515(6) 0.66314(8) 0.0290(3) Uani 0.563(2) 1 d . . P C 1
H36A H 0.6107 0.3063 0.6283 0.035 Uiso 0.563(2) 1 calc R U P C 1
C37A C 0.61519(13) 0.39538(6) 0.66769(9) 0.0330(3) Uani 0.563(2) 1 d . . P C 1
H37A H 0.5465 0.4075 0.6347 0.040 Uiso 0.563(2) 1 calc R U P C 1
C38A C 0.67335(14) 0.43851(6) 0.71824(10) 0.0383(3) Uani 0.563(2) 1 d . . P C 1
H38A H 0.6462 0.4797 0.7205 0.046 Uiso 0.563(2) 1 calc R U P C 1
C39A C 0.77240(14) 0.41929(6) 0.76533(10) 0.0377(3) Uani 0.563(2) 1 d . . P C 1
C40A C 0.81458(13) 0.36008(6) 0.76274(9) 0.0321(3) Uani 0.563(2) 1 d . . P C 1
H40A H 0.8834 0.3483 0.7958 0.039 Uiso 0.563(2) 1 calc R U P C 1
C35B C 0.75429(12) 0.31788(5) 0.71072(8) 0.0265(2) Uani 0.437(2) 1 d . . P C 2
C36B C 0.65304(12) 0.33515(6) 0.66314(8) 0.0290(3) Uani 0.437(2) 1 d . . P C 2
H36B H 0.6107 0.3063 0.6283 0.035 Uiso 0.437(2) 1 calc R U P C 2
C37B C 0.61519(13) 0.39538(6) 0.66769(9) 0.0330(3) Uani 0.437(2) 1 d . . P C 2
C38B C 0.67335(14) 0.43851(6) 0.71824(10) 0.0383(3) Uani 0.437(2) 1 d . . P C 2
H38B H 0.6462 0.4797 0.7205 0.046 Uiso 0.437(2) 1 calc R U P C 2
C39B C 0.77240(14) 0.41929(6) 0.76533(10) 0.0377(3) Uani 0.437(2) 1 d . . P C 2
H39B H 0.8133 0.4481 0.8011 0.045 Uiso 0.437(2) 1 calc R U P C 2
C40B C 0.81458(13) 0.36008(6) 0.76274(9) 0.0321(3) Uani 0.437(2) 1 d . . P C 2
H40B H 0.8834 0.3483 0.7958 0.039 Uiso 0.437(2) 1 calc R U P C 2
C41 C 0.76300(11) 0.20821(5) 0.66766(7) 0.0241(2) Uani 1 1 d . . . . .
C42 C 0.89379(12) 0.13858(6) 0.52963(8) 0.0312(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
F1A C11A 1.274(2) . ?
F1B C9B 1.155(3) . ?
F2 C14 1.3383(18) . ?
F3 C14 1.3418(16) . ?
F4 C14 1.3390(16) . ?
N1 C13 1.3486(15) . ?
N1 C7A 1.4188(15) . ?
N1 C7B 1.4188(15) . ?
N1 H1 0.8800 . ?
O1 C13 1.2314(15) . ?
C1 C6 1.3899(17) . ?
C1 C2 1.4027(17) . ?
C1 C13 1.5039(17) . ?
C2 C3 1.3897(18) . ?
C2 C14 1.4985(19) . ?
C3 C4 1.385(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.3897(18) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7A C8A 1.386(2) . ?
C7A C12A 1.3873(19) . ?
C8A C9A 1.380(2) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.370(3) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.367(3) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.383(2) . ?
C12A H12A 0.9500 . ?
C7B C8B 1.386(2) . ?
C7B C12B 1.3873(19) . ?
C8B C9B 1.380(2) . ?
C8B H8B 0.9500 . ?
C9B C10B 1.370(3) . ?
C10B C11B 1.367(3) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.383(2) . ?
C11B H11B 0.9500 . ?
C12B H12B 0.9500 . ?
F5A C23A 1.3397(17) . ?
F5B C25B 1.297(3) . ?
F6 C28 1.3420(18) . ?
F7 C28 1.3380(16) . ?
F8 C28 1.3378(18) . ?
N2 C27 1.3439(16) . ?
N2 C21A 1.4170(15) . ?
N2 C21B 1.4170(15) . ?
N2 H2 0.8800 . ?
O2 C27 1.2307(15) . ?
C15 C20 1.3896(17) . ?
C15 C16 1.3998(17) . ?
C15 C27 1.5053(17) . ?
C16 C17 1.3870(19) . ?
C16 C28 1.502(2) . ?
C17 C18 1.382(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.376(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.3898(18) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21A C22A 1.3908(18) . ?
C21A C26A 1.3923(18) . ?
C22A C23A 1.3801(18) . ?
C22A H22A 0.9500 . ?
C23A C24A 1.371(2) . ?
C24A C25A 1.382(2) . ?
C24A H24A 0.9500 . ?
C25A C26A 1.3804(19) . ?
C25A H25A 0.9500 . ?
C26A H26A 0.9500 . ?
C21B C22B 1.3908(18) . ?
C21B C26B 1.3923(18) . ?
C22B C23B 1.3801(18) . ?
C22B H22B 0.9500 . ?
C23B C24B 1.371(2) . ?
C23B H23B 0.9500 . ?
C24B C25B 1.382(2) . ?
C24B H24B 0.9500 . ?
C25B C26B 1.3804(19) . ?
C26B H26B 0.9500 . ?
F9A C39A 1.3455(19) . ?
F9B C37B 1.357(2) . ?
F10 C42 1.3406(16) . ?
F11 C42 1.3371(15) . ?
F12 C42 1.3442(15) . ?
N3 C41 1.3459(15) . ?
N3 C35A 1.4164(15) . ?
N3 C35B 1.4164(15) . ?
N3 H3A 0.8800 . ?
O3 C41 1.2323(14) . ?
C29 C34 1.3921(17) . ?
C29 C30 1.3964(17) . ?
C29 C41 1.5037(16) . ?
C30 C31 1.3917(17) . ?
C30 C42 1.4991(18) . ?
C31 C32 1.385(2) . ?
C31 H31 0.9500 . ?
C32 C33 1.374(2) . ?
C32 H32 0.9500 . ?
C33 C34 1.3856(19) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C35A C36A 1.3889(18) . ?
C35A C40A 1.3907(17) . ?
C36A C37A 1.3849(18) . ?
C36A H36A 0.9500 . ?
C37A C38A 1.380(2) . ?
C37A H37A 0.9500 . ?
C38A C39A 1.378(2) . ?
C38A H38A 0.9500 . ?
C39A C40A 1.3780(18) . ?
C40A H40A 0.9500 . ?
C35B C36B 1.3889(18) . ?
C35B C40B 1.3907(17) . ?
C36B C37B 1.3849(18) . ?
C36B H36B 0.9500 . ?
C37B C38B 1.380(2) . ?
C38B C39B 1.378(2) . ?
C38B H38B 0.9500 . ?
C39B C40B 1.3780(18) . ?
C39B H39B 0.9500 . ?
C40B H40B 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
C13 N1 C7A 127.55(11) . . ?
C13 N1 C7B 127.55(11) . . ?
C13 N1 H1 116.2 . . ?
C7A N1 H1 116.2 . . ?
C6 C1 C2 118.90(11) . . ?
C6 C1 C13 118.98(11) . . ?
C2 C1 C13 121.99(11) . . ?
C3 C2 C1 119.69(12) . . ?
C3 C2 C14 118.54(12) . . ?
C1 C2 C14 121.75(11) . . ?
C4 C3 C2 120.52(12) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C5 C4 C3 120.15(12) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 119.77(12) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C1 120.95(12) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
C8A C7A C12A 120.44(12) . . ?
C8A C7A N1 123.44(12) . . ?
C12A C7A N1 116.12(12) . . ?
C9A C8A C7A 118.42(15) . . ?
C9A C8A H8A 120.8 . . ?
C7A C8A H8A 120.8 . . ?
C10A C9A C8A 122.97(16) . . ?
C10A C9A H9A 118.5 . . ?
C8A C9A H9A 118.5 . . ?
C11A C10A C9A 116.84(14) . . ?
C11A C10A H10A 121.6 . . ?
C9A C10A H10A 121.6 . . ?
F1A C11A C10A 115.08(15) . . ?
F1A C11A C12A 121.59(18) . . ?
C10A C11A C12A 123.33(16) . . ?
C11A C12A C7A 118.00(15) . . ?
C11A C12A H12A 121.0 . . ?
C7A C12A H12A 121.0 . . ?
C8B C7B C12B 120.44(12) . . ?
C8B C7B N1 123.44(12) . . ?
C12B C7B N1 116.12(12) . . ?
C9B C8B C7B 118.42(15) . . ?
C9B C8B H8B 120.8 . . ?
C7B C8B H8B 120.8 . . ?
F1B C9B C10B 110.53(19) . . ?
F1B C9B C8B 126.2(2) . . ?
C10B C9B C8B 122.97(16) . . ?
C11B C10B C9B 116.84(14) . . ?
C11B C10B H10B 121.6 . . ?
C9B C10B H10B 121.6 . . ?
C10B C11B C12B 123.33(16) . . ?
C10B C11B H11B 118.3 . . ?
C12B C11B H11B 118.3 . . ?
C11B C12B C7B 118.00(15) . . ?
C11B C12B H12B 121.0 . . ?
C7B C12B H12B 121.0 . . ?
O1 C13 N1 124.38(11) . . ?
O1 C13 C1 120.32(11) . . ?
N1 C13 C1 115.28(10) . . ?
F2 C14 F4 106.09(12) . . ?
F2 C14 F3 106.66(12) . . ?
F4 C14 F3 106.38(11) . . ?
F2 C14 C2 113.37(11) . . ?
F4 C14 C2 111.58(12) . . ?
F3 C14 C2 112.28(11) . . ?
C27 N2 C21A 127.27(11) . . ?
C27 N2 C21B 127.27(11) . . ?
C27 N2 H2 116.4 . . ?
C21A N2 H2 116.4 . . ?
C20 C15 C16 119.20(11) . . ?
C20 C15 C27 118.77(11) . . ?
C16 C15 C27 121.84(11) . . ?
C17 C16 C15 119.57(13) . . ?
C17 C16 C28 118.94(12) . . ?
C15 C16 C28 121.48(12) . . ?
C18 C17 C16 120.64(13) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C19 C18 C17 120.10(13) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 119.91(13) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C15 C20 C19 120.55(12) . . ?
C15 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C22A C21A C26A 120.01(11) . . ?
C22A C21A N2 123.27(11) . . ?
C26A C21A N2 116.71(11) . . ?
C23A C22A C21A 117.85(12) . . ?
C23A C22A H22A 121.1 . . ?
C21A C22A H22A 121.1 . . ?
F5A C23A C24A 119.22(12) . . ?
F5A C23A C22A 116.89(13) . . ?
C24A C23A C22A 123.84(13) . . ?
C23A C24A C25A 116.97(12) . . ?
C23A C24A H24A 121.5 . . ?
C25A C24A H24A 121.5 . . ?
C26A C25A C24A 121.79(13) . . ?
C26A C25A H25A 119.1 . . ?
C24A C25A H25A 119.1 . . ?
C25A C26A C21A 119.53(13) . . ?
C25A C26A H26A 120.2 . . ?
C21A C26A H26A 120.2 . . ?
C22B C21B C26B 120.01(11) . . ?
C22B C21B N2 123.27(11) . . ?
C26B C21B N2 116.71(11) . . ?
C23B C22B C21B 117.85(12) . . ?
C23B C22B H22B 121.1 . . ?
C21B C22B H22B 121.1 . . ?
C24B C23B C22B 123.84(13) . . ?
C24B C23B H23B 118.1 . . ?
C22B C23B H23B 118.1 . . ?
C23B C24B C25B 116.97(12) . . ?
C23B C24B H24B 121.5 . . ?
C25B C24B H24B 121.5 . . ?
F5B C25B C26B 118.7(2) . . ?
F5B C25B C24B 119.5(2) . . ?
C26B C25B C24B 121.79(13) . . ?
C25B C26B C21B 119.53(13) . . ?
C25B C26B H26B 120.2 . . ?
C21B C26B H26B 120.2 . . ?
O2 C27 N2 124.95(11) . . ?
O2 C27 C15 119.51(11) . . ?
N2 C27 C15 115.51(11) . . ?
F8 C28 F7 106.56(11) . . ?
F8 C28 F6 106.71(12) . . ?
F7 C28 F6 106.60(12) . . ?
F8 C28 C16 112.47(12) . . ?
F7 C28 C16 111.56(12) . . ?
F6 C28 C16 112.53(11) . . ?
C41 N3 C35A 128.82(11) . . ?
C41 N3 C35B 128.82(11) . . ?
C41 N3 H3A 115.6 . . ?
C35A N3 H3A 115.6 . . ?
C34 C29 C30 119.02(11) . . ?
C34 C29 C41 117.97(11) . . ?
C30 C29 C41 122.87(11) . . ?
C31 C30 C29 119.78(12) . . ?
C31 C30 C42 119.00(12) . . ?
C29 C30 C42 121.20(11) . . ?
C32 C31 C30 120.18(13) . . ?
C32 C31 H31 119.9 . . ?
C30 C31 H31 119.9 . . ?
C33 C32 C31 120.34(12) . . ?
C33 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
C32 C33 C34 119.84(13) . . ?
C32 C33 H33 120.1 . . ?
C34 C33 H33 120.1 . . ?
C33 C34 C29 120.78(13) . . ?
C33 C34 H34 119.6 . . ?
C29 C34 H34 119.6 . . ?
C36A C35A C40A 120.46(11) . . ?
C36A C35A N3 123.76(11) . . ?
C40A C35A N3 115.78(11) . . ?
C37A C36A C35A 118.45(12) . . ?
C37A C36A H36A 120.8 . . ?
C35A C36A H36A 120.8 . . ?
C38A C37A C36A 122.57(13) . . ?
C38A C37A H37A 118.7 . . ?
C36A C37A H37A 118.7 . . ?
C39A C38A C37A 117.12(12) . . ?
C39A C38A H38A 121.4 . . ?
C37A C38A H38A 121.4 . . ?
F9A C39A C38A 121.20(13) . . ?
F9A C39A C40A 115.97(14) . . ?
C38A C39A C40A 122.77(12) . . ?
C39A C40A C35A 118.62(12) . . ?
C39A C40A H40A 120.7 . . ?
C35A C40A H40A 120.7 . . ?
C36B C35B C40B 120.46(11) . . ?
C36B C35B N3 123.76(11) . . ?
C40B C35B N3 115.78(11) . . ?
C37B C36B C35B 118.45(12) . . ?
C37B C36B H36B 120.8 . . ?
C35B C36B H36B 120.8 . . ?
F9B C37B C38B 120.72(13) . . ?
F9B C37B C36B 116.65(13) . . ?
C38B C37B C36B 122.57(13) . . ?
C39B C38B C37B 117.12(12) . . ?
C39B C38B H38B 121.4 . . ?
C37B C38B H38B 121.4 . . ?
C38B C39B C40B 122.77(12) . . ?
C38B C39B H39B 118.6 . . ?
C40B C39B H39B 118.6 . . ?
C39B C40B C35B 118.62(12) . . ?
C39B C40B H40B 120.7 . . ?
C35B C40B H40B 120.7 . . ?
O3 C41 N3 125.12(11) . . ?
O3 C41 C29 120.56(10) . . ?
N3 C41 C29 114.24(10) . . ?
F11 C42 F10 106.40(10) . . ?
F11 C42 F12 106.59(11) . . ?
F10 C42 F12 106.15(11) . . ?
F11 C42 C30 112.18(11) . . ?
F10 C42 C30 113.17(11) . . ?
F12 C42 C30 111.87(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
C6 C1 C2 C3 0.13(18) . . . . ?
C13 C1 C2 C3 175.91(12) . . . . ?
C6 C1 C2 C14 178.40(12) . . . . ?
C13 C1 C2 C14 -5.82(19) . . . . ?
C1 C2 C3 C4 -0.9(2) . . . . ?
C14 C2 C3 C4 -179.21(13) . . . . ?
C2 C3 C4 C5 0.7(2) . . . . ?
C3 C4 C5 C6 0.3(2) . . . . ?
C4 C5 C6 C1 -1.11(19) . . . . ?
C2 C1 C6 C5 0.87(18) . . . . ?
C13 C1 C6 C5 -175.04(11) . . . . ?
C13 N1 C7A C8A 7.0(2) . . . . ?
C13 N1 C7A C12A -173.43(12) . . . . ?
C12A C7A C8A C9A 0.5(2) . . . . ?
N1 C7A C8A C9A -179.97(13) . . . . ?
C7A C8A C9A C10A -0.3(2) . . . . ?
C8A C9A C10A C11A -0.2(3) . . . . ?
C9A C10A C11A F1A -179.39(17) . . . . ?
C9A C10A C11A C12A 0.6(3) . . . . ?
F1A C11A C12A C7A 179.58(16) . . . . ?
C10A C11A C12A C7A -0.4(2) . . . . ?
C8A C7A C12A C11A -0.2(2) . . . . ?
N1 C7A C12A C11A -179.73(12) . . . . ?
C13 N1 C7B C8B 7.0(2) . . . . ?
C13 N1 C7B C12B -173.43(12) . . . . ?
C12B C7B C8B C9B 0.5(2) . . . . ?
N1 C7B C8B C9B -179.97(13) . . . . ?
C7B C8B C9B F1B 172.9(3) . . . . ?
C7B C8B C9B C10B -0.3(2) . . . . ?
F1B C9B C10B C11B -174.4(2) . . . . ?
C8B C9B C10B C11B -0.2(3) . . . . ?
C9B C10B C11B C12B 0.6(3) . . . . ?
C10B C11B C12B C7B -0.4(2) . . . . ?
C8B C7B C12B C11B -0.2(2) . . . . ?
N1 C7B C12B C11B -179.73(12) . . . . ?
C7A N1 C13 O1 -0.2(2) . . . . ?
C7B N1 C13 O1 -0.2(2) . . . . ?
C7A N1 C13 C1 178.17(11) . . . . ?
C7B N1 C13 C1 178.17(11) . . . . ?
C6 C1 C13 O1 120.40(13) . . . . ?
C2 C1 C13 O1 -55.37(17) . . . . ?
C6 C1 C13 N1 -58.06(15) . . . . ?
C2 C1 C13 N1 126.17(12) . . . . ?
C3 C2 C14 F2 -99.20(15) . . . . ?
C1 C2 C14 F2 82.51(15) . . . . ?
C3 C2 C14 F4 20.51(18) . . . . ?
C1 C2 C14 F4 -157.78(12) . . . . ?
C3 C2 C14 F3 139.84(13) . . . . ?
C1 C2 C14 F3 -38.45(18) . . . . ?
C20 C15 C16 C17 -0.66(19) . . . . ?
C27 C15 C16 C17 -175.53(12) . . . . ?
C20 C15 C16 C28 -179.88(13) . . . . ?
C27 C15 C16 C28 5.25(19) . . . . ?
C15 C16 C17 C18 1.8(2) . . . . ?
C28 C16 C17 C18 -178.99(14) . . . . ?
C16 C17 C18 C19 -1.2(2) . . . . ?
C17 C18 C19 C20 -0.4(2) . . . . ?
C16 C15 C20 C19 -1.0(2) . . . . ?
C27 C15 C20 C19 174.06(12) . . . . ?
C18 C19 C20 C15 1.5(2) . . . . ?
C27 N2 C21A C22A 2.45(18) . . . . ?
C27 N2 C21A C26A -178.48(11) . . . . ?
C26A C21A C22A C23A -1.05(18) . . . . ?
N2 C21A C22A C23A 177.99(11) . . . . ?
C21A C22A C23A F5A -176.19(11) . . . . ?
C21A C22A C23A C24A 1.2(2) . . . . ?
F5A C23A C24A C25A 176.93(12) . . . . ?
C22A C23A C24A C25A -0.5(2) . . . . ?
C23A C24A C25A C26A -0.6(2) . . . . ?
C24A C25A C26A C21A 0.7(2) . . . . ?
C22A C21A C26A C25A 0.12(18) . . . . ?
N2 C21A C26A C25A -178.98(11) . . . . ?
C27 N2 C21B C22B 2.45(18) . . . . ?
C27 N2 C21B C26B -178.48(11) . . . . ?
C26B C21B C22B C23B -1.05(18) . . . . ?
N2 C21B C22B C23B 177.99(11) . . . . ?
C21B C22B C23B C24B 1.2(2) . . . . ?
C22B C23B C24B C25B -0.5(2) . . . . ?
C23B C24B C25B F5B -179.3(2) . . . . ?
C23B C24B C25B C26B -0.6(2) . . . . ?
F5B C25B C26B C21B 179.5(2) . . . . ?
C24B C25B C26B C21B 0.7(2) . . . . ?
C22B C21B C26B C25B 0.12(18) . . . . ?
N2 C21B C26B C25B -178.98(11) . . . . ?
C21A N2 C27 O2 0.93(19) . . . . ?
C21B N2 C27 O2 0.93(19) . . . . ?
C21A N2 C27 C15 -177.32(11) . . . . ?
C21B N2 C27 C15 -177.32(11) . . . . ?
C20 C15 C27 O2 -111.04(14) . . . . ?
C16 C15 C27 O2 63.85(16) . . . . ?
C20 C15 C27 N2 67.31(15) . . . . ?
C16 C15 C27 N2 -117.80(13) . . . . ?
C17 C16 C28 F8 96.35(15) . . . . ?
C15 C16 C28 F8 -84.43(16) . . . . ?
C17 C16 C28 F7 -23.33(19) . . . . ?
C15 C16 C28 F7 155.90(12) . . . . ?
C17 C16 C28 F6 -143.10(13) . . . . ?
C15 C16 C28 F6 36.13(18) . . . . ?
C34 C29 C30 C31 0.61(18) . . . . ?
C41 C29 C30 C31 -174.86(12) . . . . ?
C34 C29 C30 C42 -177.59(12) . . . . ?
C41 C29 C30 C42 6.95(18) . . . . ?
C29 C30 C31 C32 1.58(19) . . . . ?
C42 C30 C31 C32 179.81(13) . . . . ?
C30 C31 C32 C33 -2.2(2) . . . . ?
C31 C32 C33 C34 0.6(2) . . . . ?
C32 C33 C34 C29 1.7(2) . . . . ?
C30 C29 C34 C33 -2.23(19) . . . . ?
C41 C29 C34 C33 173.46(12) . . . . ?
C41 N3 C35A C36A -1.4(2) . . . . ?
C41 N3 C35A C40A 178.71(12) . . . . ?
C40A C35A C36A C37A 1.08(19) . . . . ?
N3 C35A C36A C37A -178.77(12) . . . . ?
C35A C36A C37A C38A -0.7(2) . . . . ?
C36A C37A C38A C39A -0.2(2) . . . . ?
C37A C38A C39A F9A 177.73(15) . . . . ?
C37A C38A C39A C40A 0.7(2) . . . . ?
F9A C39A C40A C35A -177.50(14) . . . . ?
C38A C39A C40A C35A -0.3(2) . . . . ?
C36A C35A C40A C39A -0.6(2) . . . . ?
N3 C35A C40A C39A 179.26(12) . . . . ?
C41 N3 C35B C36B -1.4(2) . . . . ?
C41 N3 C35B C40B 178.71(12) . . . . ?
C40B C35B C36B C37B 1.08(19) . . . . ?
N3 C35B C36B C37B -178.77(12) . . . . ?
C35B C36B C37B F9B 176.54(14) . . . . ?
C35B C36B C37B C38B -0.7(2) . . . . ?
F9B C37B C38B C39B -177.29(16) . . . . ?
C36B C37B C38B C39B -0.2(2) . . . . ?
C37B C38B C39B C40B 0.7(2) . . . . ?
C38B C39B C40B C35B -0.3(2) . . . . ?
C36B C35B C40B C39B -0.6(2) . . . . ?
N3 C35B C40B C39B 179.26(12) . . . . ?
C35A N3 C41 O3 0.4(2) . . . . ?
C35B N3 C41 O3 0.4(2) . . . . ?
C35A N3 C41 C29 -176.40(11) . . . . ?
C35B N3 C41 C29 -176.40(11) . . . . ?
C34 C29 C41 O3 -115.29(13) . . . . ?
C30 C29 C41 O3 60.22(17) . . . . ?
C34 C29 C41 N3 61.66(15) . . . . ?
C30 C29 C41 N3 -122.83(12) . . . . ?
C31 C30 C42 F11 -21.61(17) . . . . ?
C29 C30 C42 F11 156.60(11) . . . . ?
C31 C30 C42 F10 98.80(14) . . . . ?
C29 C30 C42 F10 -83.00(14) . . . . ?
C31 C30 C42 F12 -141.35(12) . . . . ?
C29 C30 C42 F12 36.86(17) . . . . ?

_refine_diff_density_max         0.469
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_1F2T
_database_code_depnum_ccdc_archive 'CCDC 981591'
_audit_update_record             
;
2016-03-09 deposited with the CCDC.
2016-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 F4 N O'
_chemical_formula_sum            'C14 H9 F4 N O'
_chemical_formula_weight         283.22

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   4.8913(3)
_cell_length_b                   25.8497(15)
_cell_length_c                   9.6013(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.165(7)
_cell_angle_gamma                90
_cell_volume                     1213.97(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2582
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      29.13

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.140
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5372
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.643
_diffrn_reflns_theta_max         24.990
_diffrn_reflns_theta_full        24.990
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measured_fraction_theta_full 0.913
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_Laue_measured_fraction_full 0.913
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_point_group_measured_fraction_full 0.913
_reflns_number_total             1951
_reflns_number_gt                1656
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR 92'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2013)'
_computing_molecular_graphics    Mercury
_computing_publication_material  Mercury
_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)+(0.0479P)²+0.4431P] 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         1951
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.1021
_refine_ls_wR_factor_gt          0.0966
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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 -0.2236(2) 0.33170(4) 0.37955(13) 0.0341(3) Uani 1 1 d . . . . .
F2 F 0.2259(3) 0.03076(4) 0.55849(15) 0.0438(4) Uani 1 1 d . . . . .
F3 F 0.5772(3) 0.03118(4) 0.69036(14) 0.0429(4) Uani 1 1 d . . . . .
F4 F 0.2022(3) 0.06399(4) 0.76275(14) 0.0494(4) Uani 1 1 d . . . . .
N1 N 0.1977(3) 0.28774(5) 0.52845(16) 0.0210(4) Uani 1 1 d . . . . .
H1 H 0.2296 0.2798 0.4409 0.025 Uiso 1 1 calc R U . . .
O1 O 0.1749(3) 0.25640(5) 0.74979(13) 0.0260(3) Uani 1 1 d . . . . .
C1 C 0.3848(4) 0.20340(7) 0.57708(19) 0.0197(4) Uani 1 1 d . . . . .
C2 C 0.3127(4) 0.15595(6) 0.6357(2) 0.0209(4) Uani 1 1 d . . . . .
H2 H 0.1740 0.1543 0.7046 0.025 Uiso 1 1 calc R U . . .
C3 C 0.4448(4) 0.11125(7) 0.5927(2) 0.0220(4) Uani 1 1 d . . . . .
C4 C 0.6523(4) 0.11323(7) 0.4940(2) 0.0256(5) Uani 1 1 d . . . . .
H4 H 0.7421 0.0824 0.4654 0.031 Uiso 1 1 calc R U . . .
C5 C 0.7270(4) 0.16062(7) 0.4378(2) 0.0258(5) Uani 1 1 d . . . . .
H5 H 0.8705 0.1624 0.3715 0.031 Uiso 1 1 calc R U . . .
C6 C 0.5926(4) 0.20557(7) 0.4782(2) 0.0227(4) Uani 1 1 d . . . . .
H6 H 0.6426 0.2378 0.4383 0.027 Uiso 1 1 calc R U . . .
C7 C 0.1011(4) 0.33840(6) 0.5598(2) 0.0210(4) Uani 1 1 d . . . . .
C8 C 0.2195(4) 0.36803(7) 0.6643(2) 0.0271(5) Uani 1 1 d . . . . .
H8 H 0.3651 0.3542 0.7183 0.032 Uiso 1 1 calc R U . . .
C9 C 0.1261(5) 0.41799(7) 0.6903(2) 0.0354(6) Uani 1 1 d . . . . .
H9 H 0.2071 0.4379 0.7626 0.042 Uiso 1 1 calc R U . . .
C10 C -0.0841(5) 0.43873(7) 0.6114(2) 0.0386(6) Uani 1 1 d . . . . .
H10 H -0.1463 0.4729 0.6293 0.046 Uiso 1 1 calc R U . . .
C11 C -0.2036(4) 0.40982(7) 0.5067(2) 0.0345(5) Uani 1 1 d . . . . .
H11 H -0.3480 0.4237 0.4519 0.041 Uiso 1 1 calc R U . . .
C12 C -0.1084(4) 0.36018(7) 0.4835(2) 0.0245(5) Uani 1 1 d . . . . .
C13 C 0.2427(4) 0.25120(6) 0.6269(2) 0.0203(4) Uani 1 1 d . . . . .
C14 C 0.3625(4) 0.05974(7) 0.6507(2) 0.0283(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C12 1.361(2) . ?
F2 C14 1.337(2) . ?
F3 C14 1.338(2) . ?
F4 C14 1.338(2) . ?
N1 C13 1.354(2) . ?
N1 C7 1.425(2) . ?
N1 H1 0.8800 . ?
O1 C13 1.234(2) . ?
C1 C6 1.394(3) . ?
C1 C2 1.395(2) . ?
C1 C13 1.497(2) . ?
C2 C3 1.387(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(3) . ?
C3 C14 1.499(3) . ?
C4 C5 1.388(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.379(3) . ?
C7 C8 1.387(3) . ?
C8 C9 1.393(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.383(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.381(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(3) . ?
C11 H11 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
C13 N1 C7 123.16(15) . . ?
C13 N1 H1 118.4 . . ?
C7 N1 H1 118.4 . . ?
C6 C1 C2 119.74(16) . . ?
C6 C1 C13 121.63(15) . . ?
C2 C1 C13 118.58(16) . . ?
C3 C2 C1 119.56(18) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 120.89(17) . . ?
C2 C3 C14 120.22(17) . . ?
C4 C3 C14 118.88(16) . . ?
C5 C4 C3 119.38(17) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.26(18) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 120.16(17) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C12 C7 C8 117.85(16) . . ?
C12 C7 N1 120.62(17) . . ?
C8 C7 N1 121.50(18) . . ?
C7 C8 C9 120.4(2) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C10 C9 C8 120.3(2) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 120.09(18) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 118.5(2) . . ?
C10 C11 H11 120.7 . . ?
C12 C11 H11 120.7 . . ?
F1 C12 C7 118.33(16) . . ?
F1 C12 C11 118.78(19) . . ?
C7 C12 C11 122.9(2) . . ?
O1 C13 N1 123.23(16) . . ?
O1 C13 C1 121.45(17) . . ?
N1 C13 C1 115.32(16) . . ?
F2 C14 F4 106.58(17) . . ?
F2 C14 F3 105.65(15) . . ?
F4 C14 F3 106.15(17) . . ?
F2 C14 C3 112.68(17) . . ?
F4 C14 C3 112.62(15) . . ?
F3 C14 C3 112.61(17) . . ?

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
C6 C1 C2 C3 -1.4(3) . . . . ?
C13 C1 C2 C3 -178.98(17) . . . . ?
C1 C2 C3 C4 1.4(3) . . . . ?
C1 C2 C3 C14 -177.71(18) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C14 C3 C4 C5 178.91(19) . . . . ?
C3 C4 C5 C6 -1.0(3) . . . . ?
C4 C5 C6 C1 1.0(3) . . . . ?
C2 C1 C6 C5 0.2(3) . . . . ?
C13 C1 C6 C5 177.72(18) . . . . ?
C13 N1 C7 C12 -133.60(19) . . . . ?
C13 N1 C7 C8 48.6(3) . . . . ?
C12 C7 C8 C9 0.4(3) . . . . ?
N1 C7 C8 C9 178.22(17) . . . . ?
C7 C8 C9 C10 -0.6(3) . . . . ?
C8 C9 C10 C11 0.4(3) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C8 C7 C12 F1 179.13(15) . . . . ?
N1 C7 C12 F1 1.3(3) . . . . ?
C8 C7 C12 C11 0.0(3) . . . . ?
N1 C7 C12 C11 -177.82(17) . . . . ?
C10 C11 C12 F1 -179.35(17) . . . . ?
C10 C11 C12 C7 -0.3(3) . . . . ?
C7 N1 C13 O1 8.6(3) . . . . ?
C7 N1 C13 C1 -170.81(16) . . . . ?
C6 C1 C13 O1 -141.93(19) . . . . ?
C2 C1 C13 O1 35.6(3) . . . . ?
C6 C1 C13 N1 37.5(2) . . . . ?
C2 C1 C13 N1 -144.90(17) . . . . ?
C2 C3 C14 F2 107.3(2) . . . . ?
C4 C3 C14 F2 -71.8(2) . . . . ?
C2 C3 C14 F4 -13.3(3) . . . . ?
C4 C3 C14 F4 167.58(18) . . . . ?
C2 C3 C14 F3 -133.31(19) . . . . ?
C4 C3 C14 F3 47.6(3) . . . . ?

_refine_diff_density_max         0.163
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_2F2T
_database_code_depnum_ccdc_archive 'CCDC 981592'
_audit_update_record             
;
2016-03-09 deposited with the CCDC.
2016-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 F4 N O'
_chemical_formula_sum            'C14 H9 F4 N O'
_chemical_formula_weight         283.22

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_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'
'-x, y, -z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
'x-1/2, y-1/2, -z-1/2'

_cell_length_a                   26.9156(8)
_cell_length_b                   9.6838(3)
_cell_length_c                   9.6832(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2523.88(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2519
_cell_measurement_theta_min      1.51
_cell_measurement_theta_max      30.46

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.135
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25196
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.513
_diffrn_reflns_theta_max         30.464
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3793
_reflns_number_gt                1991
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR 92'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2013)'
_computing_molecular_graphics    Mercury
_computing_publication_material  Mercury
_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)+(0.0815P)²+0.2596P] 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         3793
_refine_ls_number_parameters     213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1226
_refine_ls_R_factor_gt           0.0591
_refine_ls_wR_factor_ref         0.1777
_refine_ls_wR_factor_gt          0.1514
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
N1 N 0.14654(5) 0.42524(17) 0.26926(16) 0.0422(4) Uani 1 1 d . . . . .
H1 H 0.1359 0.4330 0.3549 0.051 Uiso 1 1 calc R U . A 1
O1 O 0.14720(5) 0.52793(15) 0.05814(14) 0.0529(4) Uani 1 1 d . . . . .
C1 C 0.10892(7) 0.6490(2) 0.2437(2) 0.0468(5) Uani 1 1 d . . . . .
C2 C 0.11897(8) 0.7801(2) 0.1923(3) 0.0606(6) Uani 1 1 d . . . . .
H2 H 0.1417 0.7910 0.1180 0.073 Uiso 1 1 calc R U . . .
C3 C 0.09605(9) 0.8944(2) 0.2485(3) 0.0726(7) Uani 1 1 d . . . . .
H3 H 0.1034 0.9840 0.2140 0.087 Uiso 1 1 calc R U . . .
C4 C 0.06234(9) 0.8785(2) 0.3556(3) 0.0710(7) Uani 1 1 d . . . . .
H4 H 0.0463 0.9571 0.3937 0.085 Uiso 1 1 calc R U . . .
C5 C 0.05206(7) 0.7478(2) 0.4070(3) 0.0560(6) Uani 1 1 d . . . . .
C6 C 0.07507(7) 0.6328(2) 0.3505(2) 0.0472(5) Uani 1 1 d . . . . .
H6 H 0.0677 0.5432 0.3849 0.057 Uiso 1 1 calc R U . . .
F1A F 0.26699(7) 0.0905(2) 0.38363(19) 0.0619(5) Uani 0.589(2) 1 d . . P B 1
C7A C 0.17391(6) 0.30451(19) 0.23445(18) 0.0396(4) Uani 0.589(2) 1 d . . P B 1
C8A C 0.16673(7) 0.2368(2) 0.11020(19) 0.0451(5) Uani 0.589(2) 1 d . . P B 1
H8A H 0.1432 0.2700 0.0451 0.054 Uiso 0.589(2) 1 calc R U P B 1
C9A C 0.19438(7) 0.1206(2) 0.0829(2) 0.0517(5) Uani 0.589(2) 1 d . . P B 1
H9A H 0.1895 0.0741 -0.0024 0.062 Uiso 0.589(2) 1 calc R U P B 1
C10A C 0.22898(7) 0.0690(2) 0.1744(2) 0.0513(5) Uani 0.589(2) 1 d . . P B 1
H10A H 0.2479 -0.0113 0.1536 0.062 Uiso 0.589(2) 1 calc R U P B 1
C11A C 0.23490(6) 0.1384(2) 0.2965(2) 0.0475(5) Uani 0.589(2) 1 d . . P B 1
C12A C 0.20797(7) 0.2553(2) 0.32973(19) 0.0439(5) Uani 0.589(2) 1 d . . P B 1
H12A H 0.2127 0.3006 0.4157 0.053 Uiso 0.589(2) 1 calc R U P B 1
F1B F 0.18579(10) 0.0504(3) -0.0232(3) 0.0619(5) Uani 0.411(2) 1 d . . P B 2
C7B C 0.17391(6) 0.30451(19) 0.23445(18) 0.0396(4) Uani 0.411(2) 1 d . . P B 2
C8B C 0.20797(7) 0.2553(2) 0.32973(19) 0.0439(5) Uani 0.411(2) 1 d . . P B 2
H8B H 0.2127 0.3006 0.4157 0.053 Uiso 0.411(2) 1 calc R U P B 2
C9B C 0.23490(6) 0.1384(2) 0.2965(2) 0.0475(5) Uani 0.411(2) 1 d . . P B 2
H9B H 0.2585 0.1048 0.3611 0.057 Uiso 0.411(2) 1 calc R U P B 2
C10B C 0.22898(7) 0.0690(2) 0.1744(2) 0.0513(5) Uani 0.411(2) 1 d . . P B 2
H10B H 0.2479 -0.0113 0.1536 0.062 Uiso 0.411(2) 1 calc R U P B 2
C11B C 0.19438(7) 0.1206(2) 0.0829(2) 0.0517(5) Uani 0.411(2) 1 d . . P B 2
C12B C 0.16673(7) 0.2368(2) 0.11020(19) 0.0451(5) Uani 0.411(2) 1 d . . P B 2
H12B H 0.1432 0.2700 0.0451 0.054 Uiso 0.411(2) 1 calc R U P B 2
C13 C 0.13557(6) 0.5290(2) 0.1808(2) 0.0438(5) Uani 1 1 d . . . . .
C14 C 0.01758(8) 0.7298(3) 0.5278(3) 0.0672(7) Uani 1 1 d . . . . .
F2A F 0.0215(5) 0.8392(7) 0.6142(6) 0.109(3) Uani 0.515(18) 1 d . . P C 2
F3A F 0.0299(4) 0.6279(12) 0.6140(10) 0.127(3) Uani 0.515(18) 1 d . . P C 2
F4A F -0.02830(18) 0.7168(17) 0.5007(7) 0.107(3) Uani 0.515(18) 1 d . . P C 2
F2B F -0.0075(5) 0.8403(6) 0.5584(19) 0.146(6) Uani 0.485(18) 1 d . . P C 1
F3B F 0.0360(3) 0.6611(14) 0.6223(8) 0.115(4) Uani 0.485(18) 1 d . . P C 1
F4B F -0.0206(3) 0.6444(10) 0.4844(8) 0.0820(18) Uani 0.485(18) 1 d . . P C 1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C13 1.353(2) . ?
N1 C7A 1.422(2) . ?
N1 C7B 1.422(2) . ?
N1 H1 0.8800 . ?
O1 C13 1.229(2) . ?
C1 C6 1.387(3) . ?
C1 C2 1.390(3) . ?
C1 C13 1.495(3) . ?
C2 C3 1.380(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(3) . ?
C5 C14 1.503(4) . ?
C6 H6 0.9500 . ?
F1A C11A 1.294(2) . ?
C7A C8A 1.384(3) . ?
C7A C12A 1.385(3) . ?
C8A C9A 1.375(3) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.379(3) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.370(3) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.382(3) . ?
C12A H12A 0.9500 . ?
F1B C11B 1.254(3) . ?
C7B C12B 1.384(3) . ?
C7B C8B 1.385(3) . ?
C8B C9B 1.382(3) . ?
C8B H8B 0.9500 . ?
C9B C10B 1.370(3) . ?
C9B H9B 0.9500 . ?
C10B C11B 1.379(3) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.375(3) . ?
C12B H12B 0.9500 . ?
C14 F3B 1.235(9) . ?
C14 F4A 1.269(6) . ?
C14 F2B 1.300(5) . ?
C14 F3A 1.334(10) . ?
C14 F2A 1.354(5) . ?
C14 F4B 1.383(6) . ?

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
C13 N1 C7A 125.00(15) . . ?
C13 N1 C7B 125.00(15) . . ?
C13 N1 H1 117.5 . . ?
C7A N1 H1 117.5 . . ?
C6 C1 C2 119.9(2) . . ?
C6 C1 C13 122.04(17) . . ?
C2 C1 C13 118.07(19) . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 119.9(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.0(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.1(2) . . ?
C6 C5 C14 119.3(2) . . ?
C4 C5 C14 120.5(2) . . ?
C5 C6 C1 119.8(2) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C8A C7A C12A 120.57(18) . . ?
C8A C7A N1 121.53(16) . . ?
C12A C7A N1 117.90(17) . . ?
C9A C8A C7A 118.64(18) . . ?
C9A C8A H8A 120.7 . . ?
C7A C8A H8A 120.7 . . ?
C8A C9A C10A 122.60(19) . . ?
C8A C9A H9A 118.7 . . ?
C10A C9A H9A 118.7 . . ?
C11A C10A C9A 117.05(19) . . ?
C11A C10A H10A 121.5 . . ?
C9A C10A H10A 121.5 . . ?
F1A C11A C10A 117.7(2) . . ?
F1A C11A C12A 119.47(19) . . ?
C10A C11A C12A 122.85(18) . . ?
C11A C12A C7A 118.29(18) . . ?
C11A C12A H12A 120.9 . . ?
C7A C12A H12A 120.9 . . ?
C12B C7B C8B 120.57(18) . . ?
C12B C7B N1 121.53(16) . . ?
C8B C7B N1 117.90(17) . . ?
C9B C8B C7B 118.29(18) . . ?
C9B C8B H8B 120.9 . . ?
C7B C8B H8B 120.9 . . ?
C10B C9B C8B 122.85(18) . . ?
C10B C9B H9B 118.6 . . ?
C8B C9B H9B 118.6 . . ?
C9B C10B C11B 117.05(19) . . ?
C9B C10B H10B 121.5 . . ?
C11B C10B H10B 121.5 . . ?
F1B C11B C12B 120.1(2) . . ?
F1B C11B C10B 117.0(2) . . ?
C12B C11B C10B 122.60(19) . . ?
C11B C12B C7B 118.64(18) . . ?
C11B C12B H12B 120.7 . . ?
C7B C12B H12B 120.7 . . ?
O1 C13 N1 123.39(18) . . ?
O1 C13 C1 121.49(18) . . ?
N1 C13 C1 115.11(16) . . ?
F3B C14 F2B 118.9(8) . . ?
F4A C14 F3A 107.4(6) . . ?
F4A C14 F2A 106.3(4) . . ?
F3A C14 F2A 100.0(5) . . ?
F3B C14 F4B 101.6(6) . . ?
F2B C14 F4B 100.1(5) . . ?
F3B C14 C5 113.0(4) . . ?
F4A C14 C5 116.8(4) . . ?
F2B C14 C5 113.7(4) . . ?
F3A C14 C5 114.8(4) . . ?
F2A C14 C5 110.0(4) . . ?
F4B C14 C5 106.9(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.1(3) . . . . ?
C13 C1 C2 C3 -178.76(19) . . . . ?
C1 C2 C3 C4 -0.9(4) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C3 C4 C5 C14 176.9(2) . . . . ?
C4 C5 C6 C1 0.9(3) . . . . ?
C14 C5 C6 C1 -176.68(18) . . . . ?
C2 C1 C6 C5 -1.1(3) . . . . ?
C13 C1 C6 C5 178.76(17) . . . . ?
C13 N1 C7A C8A -40.7(3) . . . . ?
C13 N1 C7A C12A 139.84(18) . . . . ?
C12A C7A C8A C9A -0.6(3) . . . . ?
N1 C7A C8A C9A -179.98(17) . . . . ?
C7A C8A C9A C10A 0.0(3) . . . . ?
C8A C9A C10A C11A 0.3(3) . . . . ?
C9A C10A C11A F1A 179.5(2) . . . . ?
C9A C10A C11A C12A 0.1(3) . . . . ?
F1A C11A C12A C7A 179.89(19) . . . . ?
C10A C11A C12A C7A -0.6(3) . . . . ?
C8A C7A C12A C11A 0.9(3) . . . . ?
N1 C7A C12A C11A -179.69(16) . . . . ?
C13 N1 C7B C12B -40.7(3) . . . . ?
C13 N1 C7B C8B 139.84(18) . . . . ?
C12B C7B C8B C9B 0.9(3) . . . . ?
N1 C7B C8B C9B -179.69(16) . . . . ?
C7B C8B C9B C10B -0.6(3) . . . . ?
C8B C9B C10B C11B 0.1(3) . . . . ?
C9B C10B C11B F1B -173.8(2) . . . . ?
C9B C10B C11B C12B 0.3(3) . . . . ?
F1B C11B C12B C7B 173.9(2) . . . . ?
C10B C11B C12B C7B 0.0(3) . . . . ?
C8B C7B C12B C11B -0.6(3) . . . . ?
N1 C7B C12B C11B -179.98(17) . . . . ?
C7A N1 C13 O1 2.1(3) . . . . ?
C7B N1 C13 O1 2.1(3) . . . . ?
C7A N1 C13 C1 -176.56(15) . . . . ?
C7B N1 C13 C1 -176.56(15) . . . . ?
C6 C1 C13 O1 147.58(18) . . . . ?
C2 C1 C13 O1 -32.6(3) . . . . ?
C6 C1 C13 N1 -33.8(2) . . . . ?
C2 C1 C13 N1 146.07(18) . . . . ?
C6 C5 C14 F3B 50.5(7) . . . . ?
C4 C5 C14 F3B -127.1(7) . . . . ?
C6 C5 C14 F4A -93.9(9) . . . . ?
C4 C5 C14 F4A 88.6(9) . . . . ?
C6 C5 C14 F2B -170.0(11) . . . . ?
C4 C5 C14 F2B 12.4(11) . . . . ?
C6 C5 C14 F3A 33.1(7) . . . . ?
C4 C5 C14 F3A -144.4(7) . . . . ?
C6 C5 C14 F2A 144.9(6) . . . . ?
C4 C5 C14 F2A -32.7(7) . . . . ?
C6 C5 C14 F4B -60.5(5) . . . . ?
C4 C5 C14 F4B 121.9(5) . . . . ?

_refine_diff_density_max         0.352
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_2F3T
_database_code_depnum_ccdc_archive 'CCDC 981593'
_audit_update_record             
;
2016-03-09 deposited with the CCDC.
2016-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 F4 N O'
_chemical_formula_sum            'C14 H9 F4 N O'
_chemical_formula_weight         283.22

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   28.214(7)
_cell_length_b                   5.1860(12)
_cell_length_c                   16.020(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.70(2)
_cell_angle_gamma                90
_cell_volume                     2317.1(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1835
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      28.27

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.147
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18364
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.572
_diffrn_reflns_theta_max         28.255
_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             2856
_reflns_number_gt                2360
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR 92'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2013)'
_computing_molecular_graphics    Mercury
_computing_publication_material  Mercury
_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)+(0.0444P)²+2.0826P] 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         2856
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.0973
_refine_ls_wR_factor_gt          0.0918
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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 1.12692(3) 1.10512(16) 0.79693(5) 0.0237(2) Uani 1 1 d . . . . .
F4 F 0.73225(3) 0.85494(19) 0.87700(7) 0.0362(3) Uani 1 1 d . . . . .
F3 F 0.73991(3) 0.5275(2) 0.79904(6) 0.0355(3) Uani 1 1 d . . . . .
F2 F 0.75326(3) 0.4907(2) 0.93373(6) 0.0370(3) Uani 1 1 d . . . . .
O1 O 0.97197(3) 1.11862(18) 0.88689(6) 0.0218(2) Uani 1 1 d . . . . .
N1 N 0.98985(4) 0.6914(2) 0.88013(7) 0.0163(2) Uani 1 1 d . . . . .
H1 H 0.9777 0.5349 0.8786 0.020 Uiso 1 1 calc R U . . .
C9 C 1.10811(5) 0.9146(3) 0.83955(8) 0.0176(3) Uani 1 1 d . . . . .
C8 C 1.05916(5) 0.9136(3) 0.83841(8) 0.0167(3) Uani 1 1 d . . . . .
H8 H 1.0394 1.0449 0.8102 0.020 Uiso 1 1 calc R U . . .
C7 C 1.03972(4) 0.7132(2) 0.88015(8) 0.0148(3) Uani 1 1 d . . . . .
C13 C 0.95916(4) 0.8920(2) 0.88230(8) 0.0158(3) Uani 1 1 d . . . . .
C1 C 0.90765(4) 0.8190(2) 0.87905(8) 0.0150(3) Uani 1 1 d . . . . .
C6 C 0.88780(5) 0.6041(2) 0.83453(8) 0.0165(3) Uani 1 1 d . . . . .
H6 H 0.9075 0.4930 0.8075 0.020 Uiso 1 1 calc R U . . .
C5 C 0.83937(5) 0.5526(3) 0.82975(8) 0.0172(3) Uani 1 1 d . . . . .
H5 H 0.8256 0.4081 0.7986 0.021 Uiso 1 1 calc R U . . .
C4 C 0.81107(4) 0.7137(3) 0.87072(8) 0.0167(3) Uani 1 1 d . . . . .
C14 C 0.75932(5) 0.6480(3) 0.86960(9) 0.0213(3) Uani 1 1 d . . . . .
C2 C 0.87886(5) 0.9804(2) 0.91924(8) 0.0169(3) Uani 1 1 d . . . . .
H2 H 0.8924 1.1276 0.9491 0.020 Uiso 1 1 calc R U . . .
C3 C 0.83057(5) 0.9270(3) 0.91579(8) 0.0183(3) Uani 1 1 d . . . . .
H3 H 0.8109 1.0354 0.9440 0.022 Uiso 1 1 calc R U . . .
C12 C 1.06925(5) 0.5220(3) 0.92079(8) 0.0170(3) Uani 1 1 d . . . . .
H12 H 1.0558 0.3847 0.9487 0.020 Uiso 1 1 calc R U . . .
C11 C 1.11837(5) 0.5326(3) 0.92041(8) 0.0191(3) Uani 1 1 d . . . . .
H11 H 1.1384 0.4020 0.9483 0.023 Uiso 1 1 calc R U . . .
C10 C 1.13845(5) 0.7308(3) 0.87991(8) 0.0188(3) Uani 1 1 d . . . . .
H10 H 1.1721 0.7398 0.8799 0.023 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
F1 C9 1.3539(15) . ?
F4 C14 1.3326(17) . ?
F3 C14 1.3346(16) . ?
F2 C14 1.3428(17) . ?
O1 C13 1.2284(16) . ?
N1 C13 1.3575(17) . ?
N1 C7 1.4116(16) . ?
N1 H1 0.8800 . ?
C9 C10 1.3756(19) . ?
C9 C8 1.3786(18) . ?
C8 C7 1.3925(18) . ?
C8 H8 0.9500 . ?
C7 C12 1.3918(18) . ?
C13 C1 1.4952(18) . ?
C1 C2 1.3902(18) . ?
C1 C6 1.3942(18) . ?
C6 C5 1.3831(18) . ?
C6 H6 0.9500 . ?
C5 C4 1.3872(18) . ?
C5 H5 0.9500 . ?
C4 C3 1.3887(18) . ?
C4 C14 1.4966(18) . ?
C2 C3 1.3833(18) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C12 C11 1.3877(19) . ?
C12 H12 0.9500 . ?
C11 C10 1.3818(19) . ?
C11 H11 0.9500 . ?
C10 H10 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N1 C7 125.32(11) . . ?
C13 N1 H1 117.3 . . ?
C7 N1 H1 117.3 . . ?
F1 C9 C10 118.65(12) . . ?
F1 C9 C8 117.66(12) . . ?
C10 C9 C8 123.68(12) . . ?
C9 C8 C7 117.58(12) . . ?
C9 C8 H8 121.2 . . ?
C7 C8 H8 121.2 . . ?
C12 C7 C8 120.33(11) . . ?
C12 C7 N1 117.98(11) . . ?
C8 C7 N1 121.65(11) . . ?
O1 C13 N1 123.49(12) . . ?
O1 C13 C1 121.32(12) . . ?
N1 C13 C1 115.18(11) . . ?
C2 C1 C6 120.05(12) . . ?
C2 C1 C13 117.66(11) . . ?
C6 C1 C13 122.23(11) . . ?
C5 C6 C1 119.97(12) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
C6 C5 C4 119.48(12) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C4 C3 120.98(12) . . ?
C5 C4 C14 119.19(12) . . ?
C3 C4 C14 119.77(12) . . ?
F4 C14 F3 106.56(11) . . ?
F4 C14 F2 106.26(11) . . ?
F3 C14 F2 106.25(12) . . ?
F4 C14 C4 112.77(12) . . ?
F3 C14 C4 113.04(11) . . ?
F2 C14 C4 111.46(11) . . ?
C3 C2 C1 120.13(12) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 119.38(12) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C11 C12 C7 119.83(12) . . ?
C11 C12 H12 120.1 . . ?
C7 C12 H12 120.1 . . ?
C10 C11 C12 120.80(12) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C9 C10 C11 117.78(12) . . ?
C9 C10 H10 121.1 . . ?
C11 C10 H10 121.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C9 C8 C7 178.11(11) . . . . ?
C10 C9 C8 C7 -0.50(19) . . . . ?
C9 C8 C7 C12 -0.31(18) . . . . ?
C9 C8 C7 N1 -177.93(11) . . . . ?
C13 N1 C7 C12 146.64(12) . . . . ?
C13 N1 C7 C8 -35.69(18) . . . . ?
C7 N1 C13 O1 -2.0(2) . . . . ?
C7 N1 C13 C1 178.18(11) . . . . ?
O1 C13 C1 C2 -29.59(18) . . . . ?
N1 C13 C1 C2 150.18(12) . . . . ?
O1 C13 C1 C6 147.56(13) . . . . ?
N1 C13 C1 C6 -32.66(17) . . . . ?
C2 C1 C6 C5 0.54(19) . . . . ?
C13 C1 C6 C5 -176.55(12) . . . . ?
C1 C6 C5 C4 -1.11(19) . . . . ?
C6 C5 C4 C3 0.60(19) . . . . ?
C6 C5 C4 C14 -176.37(12) . . . . ?
C5 C4 C14 F4 -152.92(12) . . . . ?
C3 C4 C14 F4 30.07(17) . . . . ?
C5 C4 C14 F3 -31.95(18) . . . . ?
C3 C4 C14 F3 151.04(12) . . . . ?
C5 C4 C14 F2 87.66(15) . . . . ?
C3 C4 C14 F2 -89.35(15) . . . . ?
C6 C1 C2 C3 0.56(19) . . . . ?
C13 C1 C2 C3 177.78(11) . . . . ?
C1 C2 C3 C4 -1.07(19) . . . . ?
C5 C4 C3 C2 0.50(19) . . . . ?
C14 C4 C3 C2 177.45(12) . . . . ?
C8 C7 C12 C11 0.62(18) . . . . ?
N1 C7 C12 C11 178.33(11) . . . . ?
C7 C12 C11 C10 -0.14(19) . . . . ?
F1 C9 C10 C11 -177.63(11) . . . . ?
C8 C9 C10 C11 0.96(19) . . . . ?
C12 C11 C10 C9 -0.62(19) . . . . ?

_refine_diff_density_max         0.300
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_3F3T
_database_code_depnum_ccdc_archive 'CCDC 981594'
_audit_update_record             
;
2016-03-09 deposited with the CCDC.
2016-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 F4 N O'
_chemical_formula_sum            'C14 H9 F4 N O'
_chemical_formula_weight         283.22

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   5.353(2)
_cell_length_b                   6.963(3)
_cell_length_c                   16.666(6)
_cell_angle_alpha                80.519(6)
_cell_angle_beta                 88.584(6)
_cell_angle_gamma                71.932(6)
_cell_volume                     582.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2055
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      25.00

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_F_000             288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.146
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6430
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.479
_diffrn_reflns_theta_max         28.054
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2578
_reflns_number_gt                2085
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR 92'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2013)'
_computing_molecular_graphics    Mercury
_computing_publication_material  Mercury
_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)+(0.0563P)²+0.2230P] 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         2578
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1198
_refine_ls_wR_factor_gt          0.1142
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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 1.22864(19) -0.44732(15) 0.98109(7) 0.0267(3) Uani 1 1 d . . . . .
F2 F 0.7263(2) 1.31935(16) 0.59924(7) 0.0340(3) Uani 1 1 d . . . . .
F3 F 0.3220(2) 1.36265(16) 0.56995(7) 0.0376(3) Uani 1 1 d . . . . .
F4 F 0.6279(2) 1.21053(15) 0.49552(6) 0.0250(3) Uani 1 1 d . . . . .
N1 N 0.9038(2) 0.3299(2) 0.79897(8) 0.0145(3) Uani 1 1 d . . . . .
H1 H 1.0319 0.3825 0.7860 0.017 Uiso 1 1 calc R U . . .
O1 O 0.4594(2) 0.39538(17) 0.78588(7) 0.0187(3) Uani 1 1 d . . . . .
C1 C 0.6428(3) 0.6492(2) 0.71986(10) 0.0144(3) Uani 1 1 d . . . . .
C2 C 0.4099(3) 0.8111(2) 0.72088(10) 0.0151(3) Uani 1 1 d . . . . .
H2 H 0.2703 0.7913 0.7541 0.018 Uiso 1 1 calc R U . . .
C3 C 0.3823(3) 1.0003(2) 0.67354(10) 0.0158(3) Uani 1 1 d . . . . .
H3 H 0.2251 1.1108 0.6747 0.019 Uiso 1 1 calc R U . . .
C4 C 0.5858(3) 1.0272(2) 0.62442(10) 0.0151(3) Uani 1 1 d . . . . .
C5 C 0.8182(3) 0.8660(2) 0.62272(10) 0.0169(3) Uani 1 1 d . . . . .
H5 H 0.9563 0.8851 0.5886 0.020 Uiso 1 1 calc R U . . .
C6 C 0.8465(3) 0.6783(2) 0.67091(10) 0.0160(3) Uani 1 1 d . . . . .
H6 H 1.0054 0.5690 0.6706 0.019 Uiso 1 1 calc R U . . .
C7 C 0.9743(3) 0.1313(2) 0.84695(9) 0.0139(3) Uani 1 1 d . . . . .
C8 C 0.8386(3) -0.0072(2) 0.84067(10) 0.0148(3) Uani 1 1 d . . . . .
H8 H 0.6885 0.0316 0.8053 0.018 Uiso 1 1 calc R U . . .
C9 C 0.9247(3) -0.2030(2) 0.88666(10) 0.0168(3) Uani 1 1 d . . . . .
H9 H 0.8329 -0.2985 0.8835 0.020 Uiso 1 1 calc R U . . .
C10 C 1.1446(3) -0.2561(2) 0.93682(10) 0.0175(4) Uani 1 1 d . . . . .
C11 C 1.2815(3) -0.1215(3) 0.94407(10) 0.0186(4) Uani 1 1 d . . . . .
H11 H 1.4322 -0.1616 0.9793 0.022 Uiso 1 1 calc R U . . .
C12 C 1.1946(3) 0.0737(2) 0.89888(10) 0.0159(3) Uani 1 1 d . . . . .
H12 H 1.2857 0.1691 0.9033 0.019 Uiso 1 1 calc R U . . .
C13 C 0.6569(3) 0.4472(2) 0.77104(10) 0.0144(3) Uani 1 1 d . . . . .
C14 C 0.5632(3) 1.2296(2) 0.57252(10) 0.0183(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C10 1.3569(18) . ?
F2 C14 1.342(2) . ?
F3 C14 1.3324(19) . ?
F4 C14 1.338(2) . ?
N1 C13 1.366(2) . ?
N1 C7 1.422(2) . ?
N1 H1 0.8800 . ?
O1 C13 1.226(2) . ?
C1 C6 1.391(2) . ?
C1 C2 1.400(2) . ?
C1 C13 1.501(2) . ?
C2 C3 1.387(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.397(2) . ?
C4 C14 1.499(2) . ?
C5 C6 1.383(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.392(2) . ?
C7 C12 1.394(2) . ?
C8 C9 1.394(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.378(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.378(2) . ?
C11 C12 1.385(2) . ?
C11 H11 0.9500 . ?
C12 H12 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
C13 N1 C7 126.52(13) . . ?
C13 N1 H1 116.7 . . ?
C7 N1 H1 116.7 . . ?
C6 C1 C2 119.78(14) . . ?
C6 C1 C13 122.80(14) . . ?
C2 C1 C13 117.40(14) . . ?
C3 C2 C1 120.23(15) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 119.51(14) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 120.60(15) . . ?
C3 C4 C14 121.03(14) . . ?
C5 C4 C14 118.37(15) . . ?
C6 C5 C4 119.71(15) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C1 120.16(14) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C8 C7 C12 120.06(15) . . ?
C8 C7 N1 122.20(14) . . ?
C12 C7 N1 117.67(14) . . ?
C7 C8 C9 119.50(14) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C10 C9 C8 119.10(15) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
F1 C10 C11 118.75(14) . . ?
F1 C10 C9 118.89(14) . . ?
C11 C10 C9 122.36(15) . . ?
C10 C11 C12 118.51(15) . . ?
C10 C11 H11 120.7 . . ?
C12 C11 H11 120.7 . . ?
C11 C12 C7 120.45(15) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
O1 C13 N1 123.81(14) . . ?
O1 C13 C1 121.51(14) . . ?
N1 C13 C1 114.69(13) . . ?
F3 C14 F4 106.85(13) . . ?
F3 C14 F2 106.83(14) . . ?
F4 C14 F2 105.73(13) . . ?
F3 C14 C4 113.16(14) . . ?
F4 C14 C4 112.12(13) . . ?
F2 C14 C4 111.68(13) . . ?

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
C6 C1 C2 C3 -0.3(2) . . . . ?
C13 C1 C2 C3 -178.58(14) . . . . ?
C1 C2 C3 C4 0.8(2) . . . . ?
C2 C3 C4 C5 -0.4(2) . . . . ?
C2 C3 C4 C14 -179.90(14) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
C14 C4 C5 C6 178.99(14) . . . . ?
C4 C5 C6 C1 1.0(2) . . . . ?
C2 C1 C6 C5 -0.7(2) . . . . ?
C13 C1 C6 C5 177.56(15) . . . . ?
C13 N1 C7 C8 31.2(2) . . . . ?
C13 N1 C7 C12 -151.74(15) . . . . ?
C12 C7 C8 C9 0.0(2) . . . . ?
N1 C7 C8 C9 177.08(14) . . . . ?
C7 C8 C9 C10 -0.7(2) . . . . ?
C8 C9 C10 F1 -179.58(14) . . . . ?
C8 C9 C10 C11 0.8(3) . . . . ?
F1 C10 C11 C12 -179.86(14) . . . . ?
C9 C10 C11 C12 -0.3(3) . . . . ?
C10 C11 C12 C7 -0.4(2) . . . . ?
C8 C7 C12 C11 0.5(2) . . . . ?
N1 C7 C12 C11 -176.64(14) . . . . ?
C7 N1 C13 O1 1.6(3) . . . . ?
C7 N1 C13 C1 -178.55(14) . . . . ?
C6 C1 C13 O1 -149.11(16) . . . . ?
C2 C1 C13 O1 29.2(2) . . . . ?
C6 C1 C13 N1 31.0(2) . . . . ?
C2 C1 C13 N1 -150.69(14) . . . . ?
C3 C4 C14 F3 -9.5(2) . . . . ?
C5 C4 C14 F3 171.07(15) . . . . ?
C3 C4 C14 F4 -130.41(15) . . . . ?
C5 C4 C14 F4 50.12(19) . . . . ?
C3 C4 C14 F2 111.13(17) . . . . ?
C5 C4 C14 F2 -68.34(19) . . . . ?

_refine_diff_density_max         0.350
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.060

