# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_C:\Users\ZHOUGR~1\Desktop\2711\OLEX2_~1\1\p
_database_code_depnum_ccdc_archive 'CCDC 1936148'
_audit_update_record             
;
2019-06-23 deposited with the CCDC.	2019-08-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H18 F6 N2 O'
_chemical_formula_weight         380.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_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                   8.7596(10)
_cell_length_b                   9.7743(19)
_cell_length_c                   11.1698(19)
_cell_angle_alpha                89.020(15)
_cell_angle_beta                 76.945(12)
_cell_angle_gamma                68.226(15)
_cell_volume                     862.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1274
_cell_measurement_theta_min      7.6920
_cell_measurement_theta_max      68.9300

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.200
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5482
_diffrn_reflns_av_unetI/netI     0.0576
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.074
_diffrn_reflns_theta_max         71.264
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3221
_reflns_number_gt                2248
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1274P)²+1.0887P]
 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         3221
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1104
_refine_ls_R_factor_gt           0.0858
_refine_ls_wR_factor_ref         0.2588
_refine_ls_wR_factor_gt          0.2326
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0934(3) 0.2584(3) 0.0379(2) 0.0331(6) Uani 1 1 d . . . . .
N2 N 0.3523(4) 0.1178(3) -0.0858(3) 0.0341(7) Uani 1 1 d . . . . .
N1 N 0.3038(4) 0.0942(4) 0.1213(3) 0.0397(8) Uani 1 1 d . . . . .
H1 H 0.3978 0.0151 0.1079 0.048 Uiso 1 1 calc R U . . .
C9 C 0.2506(4) 0.1545(4) 0.0228(3) 0.0324(8) Uani 1 1 d . . . . .
C8 C 0.4195(4) 0.1850(4) -0.2908(3) 0.0337(8) Uani 1 1 d . . . . .
H8 H 0.5299 0.1676 -0.2808 0.040 Uiso 1 1 calc R U . . .
C6 C 0.1404(5) 0.1860(4) -0.2138(3) 0.0354(8) Uani 1 1 d . . . . .
H6 H 0.0579 0.1689 -0.1507 0.043 Uiso 1 1 calc R U . . .
C4 C 0.1034(5) 0.2309(4) -0.3255(4) 0.0367(8) Uani 1 1 d . . . . .
C3 C 0.2207(5) 0.2546(4) -0.4211(4) 0.0388(9) Uani 1 1 d . . . . .
H3 H 0.1931 0.2870 -0.4970 0.047 Uiso 1 1 calc R U . . .
F5 F 0.5823(4) 0.3346(4) -0.4711(3) 0.0799(10) Uani 1 1 d . . . . .
C2 C 0.3795(5) 0.2292(4) -0.4020(4) 0.0376(9) Uani 1 1 d . . . . .
C12 C -0.0228(4) 0.2982(4) 0.1604(3) 0.0349(8) Uani 1 1 d . . . . .
F1 F -0.1718(4) 0.2331(6) -0.2525(3) 0.1126(17) Uani 1 1 d . . . . .
C7 C 0.2996(4) 0.1657(4) -0.1934(3) 0.0324(8) Uani 1 1 d . . . . .
F4 F 0.4585(5) 0.3007(6) -0.6002(3) 0.126(2) Uani 1 1 d . . . . .
C13 C -0.1483(5) 0.4519(4) 0.1513(4) 0.0403(9) Uani 1 1 d . . . . .
H13A H -0.0854 0.5172 0.1243 0.048 Uiso 1 1 calc R U . . .
H13B H -0.2222 0.4912 0.2342 0.048 Uiso 1 1 calc R U . . .
F2 F -0.1394(4) 0.3818(4) -0.3862(5) 0.1061(15) Uani 1 1 d . . . . .
C14 C -0.2584(5) 0.4573(5) 0.0626(4) 0.0441(10) Uani 1 1 d . . . . .
H14A H -0.1870 0.4310 -0.0224 0.053 Uiso 1 1 calc R U . . .
H14B H -0.3427 0.5590 0.0658 0.053 Uiso 1 1 calc R U . . .
F3 F -0.0575(4) 0.1603(5) -0.4353(4) 0.1039(14) Uani 1 1 d . . . . .
C17 C -0.1097(5) 0.1871(5) 0.1850(4) 0.0428(10) Uani 1 1 d . . . . .
H17A H -0.0220 0.0862 0.1765 0.051 Uiso 1 1 calc R U . . .
H17B H -0.1780 0.2059 0.2710 0.051 Uiso 1 1 calc R U . . .
C5 C -0.0671(5) 0.2532(5) -0.3469(4) 0.0455(10) Uani 1 1 d . . . . .
C10 C 0.2201(5) 0.1480(5) 0.2480(4) 0.0423(9) Uani 1 1 d . . . . .
H10A H 0.3032 0.1549 0.2924 0.051 Uiso 1 1 calc R U . . .
H10B H 0.1707 0.0783 0.2891 0.051 Uiso 1 1 calc R U . . .
C16 C -0.2238(5) 0.1938(5) 0.0990(5) 0.0491(11) Uani 1 1 d . . . . .
H16A H -0.2868 0.1287 0.1267 0.059 Uiso 1 1 calc R U . . .
H16B H -0.1532 0.1562 0.0149 0.059 Uiso 1 1 calc R U . . .
C11 C 0.0816(5) 0.2989(5) 0.2521(4) 0.0433(9) Uani 1 1 d . . . . .
H11A H 0.1328 0.3739 0.2319 0.052 Uiso 1 1 calc R U . . .
H11B H 0.0074 0.3258 0.3362 0.052 Uiso 1 1 calc R U . . .
F6 F 0.6441(5) 0.1211(4) -0.5384(4) 0.1193(18) Uani 1 1 d . . . . .
C1 C 0.5120(6) 0.2469(5) -0.5035(4) 0.0491(11) Uani 1 1 d . . . . .
C15 C -0.3498(5) 0.3507(5) 0.0949(5) 0.0519(11) Uani 1 1 d . . . . .
H15A H -0.4308 0.3835 0.1761 0.062 Uiso 1 1 calc R U . . .
H15B H -0.4145 0.3515 0.0326 0.062 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
O1 C9 1.349(4) . ?
O1 C12 1.468(4) . ?
N2 C9 1.296(5) . ?
N2 C7 1.396(5) . ?
N1 C9 1.334(5) . ?
N1 C10 1.445(5) . ?
C8 C2 1.385(5) . ?
C8 C7 1.395(5) . ?
C6 C4 1.383(5) . ?
C6 C7 1.405(5) . ?
C4 C3 1.387(5) . ?
C4 C5 1.501(5) . ?
C3 C2 1.386(5) . ?
F5 C1 1.322(5) . ?
C2 C1 1.487(6) . ?
C12 C13 1.516(5) . ?
C12 C11 1.521(5) . ?
C12 C17 1.530(5) . ?
F1 C5 1.297(5) . ?
F4 C1 1.299(5) . ?
C13 C14 1.519(6) . ?
F2 C5 1.300(5) . ?
C14 C15 1.527(6) . ?
F3 C5 1.320(5) . ?
C17 C16 1.520(6) . ?
C10 C11 1.517(5) . ?
C16 C15 1.528(6) . ?
F6 C1 1.326(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
C9 O1 C12 120.5(3) . . ?
C9 N2 C7 122.7(3) . . ?
C9 N1 C10 125.5(3) . . ?
N2 C9 N1 120.0(3) . . ?
N2 C9 O1 120.5(3) . . ?
N1 C9 O1 119.4(3) . . ?
C2 C8 C7 120.8(3) . . ?
C4 C6 C7 120.2(3) . . ?
C6 C4 C3 122.0(3) . . ?
C6 C4 C5 120.1(4) . . ?
C3 C4 C5 117.9(3) . . ?
C2 C3 C4 117.5(4) . . ?
C8 C2 C3 121.6(3) . . ?
C8 C2 C1 118.8(3) . . ?
C3 C2 C1 119.6(4) . . ?
O1 C12 C13 104.5(3) . . ?
O1 C12 C11 107.1(3) . . ?
C13 C12 C11 111.4(3) . . ?
O1 C12 C17 108.3(3) . . ?
C13 C12 C17 111.4(3) . . ?
C11 C12 C17 113.6(3) . . ?
N2 C7 C8 116.8(3) . . ?
N2 C7 C6 125.2(3) . . ?
C8 C7 C6 117.8(3) . . ?
C12 C13 C14 113.6(3) . . ?
C13 C14 C15 111.1(3) . . ?
C16 C17 C12 113.6(3) . . ?
F1 C5 F2 108.9(4) . . ?
F1 C5 F3 104.4(4) . . ?
F2 C5 F3 103.1(4) . . ?
F1 C5 C4 114.5(3) . . ?
F2 C5 C4 112.7(4) . . ?
F3 C5 C4 112.3(4) . . ?
N1 C10 C11 109.5(3) . . ?
C17 C16 C15 112.1(4) . . ?
C10 C11 C12 110.3(3) . . ?
F4 C1 F5 105.4(4) . . ?
F4 C1 F6 108.6(5) . . ?
F5 C1 F6 102.1(4) . . ?
F4 C1 C2 114.2(4) . . ?
F5 C1 C2 113.5(4) . . ?
F6 C1 C2 112.1(4) . . ?
C16 C15 C14 110.9(3) . . ?

_refine_diff_density_max         0.731
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.075

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_C:\Users\win7\Desktop\2648\OLEX2_~1\exp_2648
_database_code_depnum_ccdc_archive 'CCDC 1936149'
_audit_update_record             
;
2019-06-23 deposited with the CCDC.	2019-08-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H18 F6 N2 O'
_chemical_formula_weight         380.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   9.8103(17)
_cell_length_b                   21.4003(18)
_cell_length_c                   9.3414(10)
_cell_angle_alpha                90
_cell_angle_beta                 115.226(17)
_cell_angle_gamma                90
_cell_volume                     1774.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1321
_cell_measurement_theta_min      5.6190
_cell_measurement_theta_max      70.3400

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.167
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6485
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.132
_diffrn_reflns_theta_max         70.582
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3343
_reflns_number_gt                2218
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1036P)²+0.9343P] 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         3343
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0656
_refine_ls_wR_factor_ref         0.2148
_refine_ls_wR_factor_gt          0.1826
_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
O1 O 0.0461(3) 0.70346(9) 0.3499(2) 0.0536(6) Uani 1 1 d . . . . .
N1 N 0.0855(3) 0.75411(11) 0.1549(2) 0.0498(6) Uani 1 1 d . . . . .
H12 H 0.0618 0.7552 0.0528 0.060 Uiso 1 1 calc R U . . .
F5 F 0.3045(3) 0.95266(10) 0.0495(3) 0.0918(8) Uani 1 1 d . . . . .
C9 C 0.0261(4) 0.70638(12) 0.2093(3) 0.0458(7) Uani 1 1 d . . . . .
F2 F 0.4551(3) 0.77775(13) 0.7248(2) 0.0987(9) Uani 1 1 d . . . . .
N2 N -0.0547(3) 0.66266(11) 0.1050(3) 0.0508(7) Uani 1 1 d . . . . .
C10 C 0.1810(4) 0.80106(13) 0.2496(3) 0.0478(7) Uani 1 1 d . . . . .
F3 F 0.5812(3) 0.85792(15) 0.7288(3) 0.1108(10) Uani 1 1 d . . . . .
C15 C 0.1898(4) 0.85696(13) 0.1773(3) 0.0506(8) Uani 1 1 d . . . . .
H18 H 0.1312 0.8625 0.0669 0.061 Uiso 1 1 calc R U . . .
C11 C 0.2700(4) 0.79380(14) 0.4117(3) 0.0519(8) Uani 1 1 d . . . . .
H14 H 0.2697 0.7553 0.4623 0.062 Uiso 1 1 calc R U . . .
C14 C 0.3670(4) 0.89873(16) 0.4270(3) 0.0593(9) Uani 1 1 d . . . . .
H16 H 0.4284 0.9321 0.4877 0.071 Uiso 1 1 calc R U . . .
C16 C 0.2837(4) 0.90444(14) 0.2658(3) 0.0546(8) Uani 1 1 d . . . . .
F4 F 0.4017(4) 1.00014(13) 0.2676(3) 0.1414(15) Uani 1 1 d . . . . .
F6 F 0.1659(4) 0.99690(12) 0.1364(4) 0.1127(10) Uani 1 1 d . . . . .
C8 C -0.1067(4) 0.60730(15) 0.1620(4) 0.0607(9) Uani 1 1 d . . . . .
H9A H -0.1808 0.6191 0.2034 0.073 Uiso 1 1 calc R U . . .
H9B H -0.0211 0.5854 0.2461 0.073 Uiso 1 1 calc R U . . .
C12 C 0.3586(4) 0.84295(15) 0.4980(3) 0.0560(8) Uani 1 1 d . . . . .
F1 F 0.3788(4) 0.86676(19) 0.7497(3) 0.1388(14) Uani 1 1 d . . . . .
C17 C 0.2899(5) 0.96358(16) 0.1814(4) 0.0688(10) Uani 1 1 d . . . . .
C4 C -0.0850(4) 0.65700(15) -0.0626(3) 0.0559(8) Uani 1 1 d . . . . .
H2 H 0.0034 0.6729 -0.0787 0.067 Uiso 1 1 calc R U . . .
C13 C 0.4443(5) 0.83687(19) 0.6740(4) 0.0721(11) Uani 1 1 d . . . . .
C7 C -0.1793(5) 0.56684(16) 0.0144(4) 0.0710(10) Uani 1 1 d . . . . .
H8A H -0.1647 0.5219 0.0417 0.085 Uiso 1 1 calc R U . . .
H8B H -0.2886 0.5755 -0.0421 0.085 Uiso 1 1 calc R U . . .
C3 C -0.2250(5) 0.69185(18) -0.1690(4) 0.0703(10) Uani 1 1 d . . . . .
H3A H -0.2046 0.7373 -0.1587 0.084 Uiso 1 1 calc R U . . .
H3B H -0.3066 0.6832 -0.1360 0.084 Uiso 1 1 calc R U . . .
C6 C -0.0972(5) 0.58570(16) -0.0853(4) 0.0657(9) Uani 1 1 d . . . . .
H7 H 0.0069 0.5679 -0.0347 0.079 Uiso 1 1 calc R U . . .
C5 C -0.1686(6) 0.5657(2) -0.2589(4) 0.0859(13) Uani 1 1 d . . . . .
H6A H -0.0936 0.5710 -0.3029 0.103 Uiso 1 1 calc R U . . .
H6B H -0.1942 0.5208 -0.2649 0.103 Uiso 1 1 calc R U . . .
C1 C -0.3071(6) 0.6015(2) -0.3586(4) 0.0916(15) Uani 1 1 d . . . . .
H5A H -0.3881 0.5915 -0.3257 0.110 Uiso 1 1 calc R U . . .
H5B H -0.3418 0.5890 -0.4707 0.110 Uiso 1 1 calc R U . . .
C2 C -0.2761(6) 0.6721(2) -0.3424(4) 0.0909(14) Uani 1 1 d . . . . .
H4A H -0.1967 0.6825 -0.3774 0.109 Uiso 1 1 calc R U . . .
H4B H -0.3687 0.6952 -0.4104 0.109 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
O1 C9 1.244(3) . ?
N1 C9 1.376(4) . ?
N1 C10 1.401(4) . ?
F5 C17 1.320(4) . ?
C9 N2 1.340(4) . ?
F2 C13 1.339(5) . ?
N2 C4 1.469(3) . ?
N2 C8 1.476(4) . ?
C10 C15 1.395(4) . ?
C10 C11 1.397(4) . ?
F3 C13 1.297(4) . ?
C15 C16 1.384(4) . ?
C11 C12 1.384(4) . ?
C14 C16 1.379(4) . ?
C14 C12 1.385(5) . ?
C16 C17 1.506(4) . ?
F4 C17 1.308(4) . ?
F6 C17 1.315(5) . ?
C8 C7 1.524(4) . ?
C12 C13 1.499(4) . ?
F1 C13 1.308(5) . ?
C4 C3 1.506(5) . ?
C4 C6 1.538(4) . ?
C7 C6 1.523(5) . ?
C3 C2 1.537(5) . ?
C6 C5 1.528(4) . ?
C5 C1 1.490(6) . ?
C1 C2 1.537(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
C9 N1 C10 124.9(2) . . ?
O1 C9 N2 120.7(3) . . ?
O1 C9 N1 121.8(2) . . ?
N2 C9 N1 117.5(2) . . ?
C9 N2 C4 128.4(2) . . ?
C9 N2 C8 119.1(2) . . ?
C4 N2 C8 112.0(2) . . ?
C15 C10 C11 118.8(3) . . ?
C15 C10 N1 118.1(2) . . ?
C11 C10 N1 123.1(3) . . ?
C16 C15 C10 120.2(3) . . ?
C12 C11 C10 119.6(3) . . ?
C16 C14 C12 118.1(3) . . ?
C14 C16 C15 121.4(3) . . ?
C14 C16 C17 120.6(3) . . ?
C15 C16 C17 118.0(3) . . ?
N2 C8 C7 103.3(2) . . ?
C11 C12 C14 121.8(3) . . ?
C11 C12 C13 119.5(3) . . ?
C14 C12 C13 118.7(3) . . ?
F4 C17 F6 106.9(3) . . ?
F4 C17 F5 106.5(4) . . ?
F6 C17 F5 104.5(3) . . ?
F4 C17 C16 113.0(3) . . ?
F6 C17 C16 112.7(4) . . ?
F5 C17 C16 112.6(3) . . ?
N2 C4 C3 112.0(3) . . ?
N2 C4 C6 101.4(2) . . ?
C3 C4 C6 113.9(3) . . ?
F3 C13 F1 106.3(4) . . ?
F3 C13 F2 106.0(3) . . ?
F1 C13 F2 104.6(3) . . ?
F3 C13 C12 113.9(3) . . ?
F1 C13 C12 112.0(3) . . ?
F2 C13 C12 113.1(3) . . ?
C6 C7 C8 103.8(3) . . ?
C4 C3 C2 110.8(3) . . ?
C7 C6 C5 116.9(3) . . ?
C7 C6 C4 102.1(3) . . ?
C5 C6 C4 113.4(3) . . ?
C1 C5 C6 113.8(3) . . ?
C5 C1 C2 110.8(4) . . ?
C3 C2 C1 109.6(3) . . ?

_refine_diff_density_max         0.339
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.053

_shelxl_version_number           2013-4

