# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_FI
_database_code_depnum_ccdc_archive 'CCDC 1886184'
_audit_update_record             
;
2019-01-29 deposited with the CCDC.
2019-02-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H10 F6 N2 O2'
_chemical_formula_weight         376.26

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                   5.0637(4)
_cell_length_b                   4.9677(4)
_cell_length_c                   29.092(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.332(2)
_cell_angle_gamma                90
_cell_volume                     729.71(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    7945
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      30.46

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.712
_exptl_crystal_F_000             380
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.165
_shelx_estimated_absorpt_T_min   0.934
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7001
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS-2014/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture CMOS PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11752
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         2.809
_diffrn_reflns_theta_max         30.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2200
_reflns_number_gt                1975
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'PLATON(Spek, 2009) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'WINGX (Farrugia, 2014) and PLATON'
_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)+(0.0568P)²+0.2622P] 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         2200
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.1021
_refine_ls_wR_factor_gt          0.0984
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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 0.87649(16) 0.30288(19) 0.77387(2) 0.0333(2) Uani 1 1 d . . . . .
F1 F 0.54912(14) 0.27661(16) 0.81664(2) 0.02596(18) Uani 1 1 d . . . . .
F3 F 0.64294(15) 0.65449(16) 0.78537(3) 0.0309(2) Uani 1 1 d . . . . .
O1 O 0.71473(14) 0.11002(18) 0.96744(3) 0.02103(19) Uani 1 1 d . . . . .
N1 N 1.15019(16) 0.22240(17) 0.96186(3) 0.01401(17) Uani 1 1 d . . . . .
H1 H 1.309474 0.201454 0.975696 0.017 Uiso 1 1 calc R U . . .
C7 C 0.7495(2) 0.4350(2) 0.80586(3) 0.0192(2) Uani 1 1 d . . . . .
C3 C 0.93494(18) 0.5028(2) 0.84701(3) 0.01459(19) Uani 1 1 d . . . . .
C2 C 0.93868(18) 0.3415(2) 0.88600(3) 0.01446(19) Uani 1 1 d . . . . .
H2 H 0.814574 0.199264 0.887844 0.017 Uiso 1 1 calc R U . . .
C1 C 1.12734(18) 0.39147(19) 0.92242(3) 0.01282(18) Uani 1 1 d . . . . .
C8 C 0.95119(18) 0.09218(19) 0.97985(3) 0.01361(19) Uani 1 1 d . . . . .
C4 C 1.1127(2) 0.7146(2) 0.84389(3) 0.0180(2) Uani 1 1 d . . . . .
H3 H 1.106819 0.824809 0.817148 0.022 Uiso 1 1 calc R U . . .
C5 C 1.2989(2) 0.7619(2) 0.88056(4) 0.0189(2) Uani 1 1 d . . . . .
H4 H 1.421046 0.906060 0.878861 0.023 Uiso 1 1 calc R U . . .
C6 C 1.30846(19) 0.6007(2) 0.91972(3) 0.0159(2) Uani 1 1 d . . . . .
H5 H 1.437794 0.633042 0.944483 0.019 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
F2 C7 1.3418(13) . ?
F1 C7 1.3398(13) . ?
F3 C7 1.3370(13) . ?
O1 C8 1.2274(11) . ?
N1 C8 1.3369(12) . ?
N1 C1 1.4196(12) . ?
N1 H1 0.8800 . ?
C7 C3 1.5026(14) . ?
C3 C2 1.3877(13) . ?
C3 C4 1.3918(15) . ?
C2 C1 1.3942(13) . ?
C2 H2 0.9500 . ?
C1 C6 1.3921(13) . ?
C8 C8 1.5398(18) 3_757 ?
C4 C5 1.3894(15) . ?
C4 H3 0.9500 . ?
C5 C6 1.3905(14) . ?
C5 H4 0.9500 . ?
C6 H5 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
C8 N1 C1 125.79(8) . . ?
C8 N1 H1 117.1 . . ?
C1 N1 H1 117.1 . . ?
F3 C7 F1 107.20(9) . . ?
F3 C7 F2 106.73(9) . . ?
F1 C7 F2 106.63(9) . . ?
F3 C7 C3 112.28(9) . . ?
F1 C7 C3 112.59(8) . . ?
F2 C7 C3 111.05(8) . . ?
C2 C3 C4 121.38(9) . . ?
C2 C3 C7 119.39(9) . . ?
C4 C3 C7 119.07(9) . . ?
C3 C2 C1 118.99(9) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C6 C1 C2 120.43(9) . . ?
C6 C1 N1 118.25(8) . . ?
C2 C1 N1 121.22(9) . . ?
O1 C8 N1 126.68(9) . . ?
O1 C8 C8 121.12(11) . 3_757 ?
N1 C8 C8 112.20(10) . 3_757 ?
C5 C4 C3 118.85(9) . . ?
C5 C4 H3 120.6 . . ?
C3 C4 H3 120.6 . . ?
C4 C5 C6 120.74(10) . . ?
C4 C5 H4 119.6 . . ?
C6 C5 H4 119.6 . . ?
C5 C6 C1 119.59(9) . . ?
C5 C6 H5 120.2 . . ?
C1 C6 H5 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F3 C7 C3 C2 141.34(10) . . . . ?
F1 C7 C3 C2 20.23(13) . . . . ?
F2 C7 C3 C2 -99.25(11) . . . . ?
F3 C7 C3 C4 -43.32(13) . . . . ?
F1 C7 C3 C4 -164.43(9) . . . . ?
F2 C7 C3 C4 76.08(12) . . . . ?
C4 C3 C2 C1 -0.89(15) . . . . ?
C7 C3 C2 C1 174.33(9) . . . . ?
C3 C2 C1 C6 0.23(14) . . . . ?
C3 C2 C1 N1 -176.10(9) . . . . ?
C8 N1 C1 C6 151.12(10) . . . . ?
C8 N1 C1 C2 -32.48(15) . . . . ?
C1 N1 C8 O1 -5.21(17) . . . . ?
C1 N1 C8 C8 175.21(10) . . . 3_757 ?
C2 C3 C4 C5 0.71(15) . . . . ?
C7 C3 C4 C5 -174.53(9) . . . . ?
C3 C4 C5 C6 0.13(16) . . . . ?
C4 C5 C6 C1 -0.77(16) . . . . ?
C2 C1 C6 C5 0.59(15) . . . . ?
N1 C1 C6 C5 177.02(9) . . . . ?

_refine_diff_density_max         0.406
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.070

####################################################################### 
# 
# 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_FII
_database_code_depnum_ccdc_archive 'CCDC 1886185'
_audit_update_record             
;
2018-12-19 deposited with the CCDC.
2019-02-07 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H10 F6 N2 O2'
_chemical_formula_weight         376.26

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                   4.9806(4)
_cell_length_b                   11.5051(8)
_cell_length_c                   14.8528(12)
_cell_angle_alpha                68.367(5)
_cell_angle_beta                 80.383(4)
_cell_angle_gamma                78.374(4)
_cell_volume                     770.89(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6745
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      29.98

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_F_000             380
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.157
_shelx_estimated_absorpt_T_min   0.926
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6829
_exptl_absorpt_correction_T_max  0.7460
_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 D8 Venture CMOS PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25315
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_av_R_equivalents  0.0658
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.810
_diffrn_reflns_theta_max         30.146
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4468
_reflns_number_gt                3138
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'PLATON(Spek, 2009) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'WINGX (Farrugia, 2014) and PLATON'
_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)+(0.0458P)²+0.5515P] 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         4468
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1217
_refine_ls_wR_factor_gt          0.1071
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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 0.1861(3) 0.65949(15) 0.12315(11) 0.0152(3) Uani 1 1 d . . . . .
C2 C 0.3251(3) 0.62977(16) 0.20416(12) 0.0164(3) Uani 1 1 d . . . . .
H2 H 0.474079 0.561852 0.218274 0.020 Uiso 1 1 calc R U . . .
C3 C 0.2417(3) 0.70158(16) 0.26427(12) 0.0175(3) Uani 1 1 d . . . . .
C4 C 0.0285(4) 0.80251(17) 0.24407(13) 0.0217(4) Uani 1 1 d . . . . .
H4 H -0.023791 0.851330 0.285421 0.026 Uiso 1 1 calc R U . . .
C5 C -0.1071(4) 0.83111(18) 0.16284(14) 0.0268(4) Uani 1 1 d . . . . .
H5 H -0.253569 0.900127 0.148048 0.032 Uiso 1 1 calc R U . . .
C6 C -0.0296(4) 0.75909(17) 0.10262(13) 0.0225(4) Uani 1 1 d . . . . .
H6 H -0.124957 0.778331 0.047337 0.027 Uiso 1 1 calc R U . . .
C7 C 0.3718(4) 0.66542(19) 0.35604(13) 0.0254(4) Uani 1 1 d . . . . .
C9 C 0.5091(3) 1.18151(15) 0.39564(11) 0.0148(3) Uani 1 1 d . . . . .
C14 C 0.3337(3) 1.28538(15) 0.40992(12) 0.0184(3) Uani 1 1 d . . . . .
H9 H 0.352679 1.310747 0.462299 0.022 Uiso 1 1 calc R U . . .
C13 C 0.1321(4) 1.35176(16) 0.34831(13) 0.0215(4) Uani 1 1 d . . . . .
H10 H 0.013736 1.422578 0.358575 0.026 Uiso 1 1 calc R U . . .
C12 C 0.1012(3) 1.31569(16) 0.27148(12) 0.0200(3) Uani 1 1 d . . . . .
H11 H -0.035724 1.361701 0.228574 0.024 Uiso 1 1 calc R U . . .
C11 C 0.2743(3) 1.21131(15) 0.25881(11) 0.0168(3) Uani 1 1 d . . . . .
C10 C 0.4785(3) 1.14321(15) 0.31975(11) 0.0161(3) Uani 1 1 d . . . . .
H13 H 0.595047 1.071791 0.309812 0.019 Uiso 1 1 calc R U . . .
C15 C 0.2499(4) 1.17058(17) 0.17608(12) 0.0200(3) Uani 1 1 d . . . . .
C8 C 0.5019(3) 0.52998(15) 0.03842(11) 0.0142(3) Uani 1 1 d . . . . .
C16 C 0.9038(3) 1.01717(15) 0.46019(11) 0.0140(3) Uani 1 1 d . . . . .
F1 F 0.6013(3) 0.58125(12) 0.36139(9) 0.0372(3) Uani 1 1 d . . . . .
F2 F 0.2003(3) 0.61459(14) 0.43520(8) 0.0462(4) Uani 1 1 d . . . . .
F3 F 0.4398(2) 0.76559(12) 0.36872(9) 0.0354(3) Uani 1 1 d . . . . .
F4 F 0.3032(3) 1.04581(11) 0.19826(9) 0.0418(3) Uani 1 1 d . . . . .
F5 F 0.4277(3) 1.21672(14) 0.09877(8) 0.0449(4) Uani 1 1 d . . . . .
F6 F 0.0018(3) 1.20727(16) 0.14498(10) 0.0515(4) Uani 1 1 d . . . . .
N1 N 0.2532(3) 0.58780(13) 0.06050(10) 0.0150(3) Uani 1 1 d . . . . .
H1 H 0.116189 0.580706 0.033294 0.018 Uiso 1 1 calc R U . . .
N2 N 0.7124(3) 1.11814(13) 0.46023(10) 0.0154(3) Uani 1 1 d . . . . .
H2A H 0.714427 1.148482 0.506477 0.018 Uiso 1 1 calc R U . . .
O1 O 0.7164(2) 0.52252(12) 0.07198(9) 0.0207(3) Uani 1 1 d . . . . .
O2 O 0.9315(2) 0.95588(11) 0.40642(9) 0.0197(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
C1 C6 1.384(2) . ?
C1 C2 1.387(2) . ?
C1 N1 1.4173(19) . ?
C2 C3 1.391(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.385(2) . ?
C3 C7 1.490(2) . ?
C4 C5 1.382(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 F1 1.333(2) . ?
C7 F2 1.346(2) . ?
C7 F3 1.348(2) . ?
C9 C10 1.393(2) . ?
C9 C14 1.393(2) . ?
C9 N2 1.410(2) . ?
C14 C13 1.383(2) . ?
C14 H9 0.9500 . ?
C13 C12 1.390(2) . ?
C13 H10 0.9500 . ?
C12 C11 1.384(2) . ?
C12 H11 0.9500 . ?
C11 C10 1.390(2) . ?
C11 C15 1.497(2) . ?
C10 H13 0.9500 . ?
C15 F6 1.325(2) . ?
C15 F4 1.329(2) . ?
C15 F5 1.336(2) . ?
C8 O1 1.2277(19) . ?
C8 N1 1.333(2) . ?
C8 C8 1.540(3) 2_665 ?
C16 O2 1.2220(19) . ?
C16 N2 1.346(2) . ?
C16 C16 1.534(3) 2_776 ?
N1 H1 0.8800 . ?
N2 H2A 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 120.46(14) . . ?
C6 C1 N1 117.81(14) . . ?
C2 C1 N1 121.71(14) . . ?
C1 C2 C3 118.54(15) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 121.69(15) . . ?
C4 C3 C7 118.50(14) . . ?
C2 C3 C7 119.71(15) . . ?
C5 C4 C3 118.99(15) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 120.20(16) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 120.11(16) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
F1 C7 F2 106.45(16) . . ?
F1 C7 F3 106.40(15) . . ?
F2 C7 F3 105.38(14) . . ?
F1 C7 C3 113.75(14) . . ?
F2 C7 C3 111.84(15) . . ?
F3 C7 C3 112.44(16) . . ?
C10 C9 C14 119.77(15) . . ?
C10 C9 N2 122.33(14) . . ?
C14 C9 N2 117.89(14) . . ?
C13 C14 C9 120.39(15) . . ?
C13 C14 H9 119.8 . . ?
C9 C14 H9 119.8 . . ?
C14 C13 C12 120.51(16) . . ?
C14 C13 H10 119.7 . . ?
C12 C13 H10 119.7 . . ?
C11 C12 C13 118.58(15) . . ?
C11 C12 H11 120.7 . . ?
C13 C12 H11 120.7 . . ?
C12 C11 C10 121.92(15) . . ?
C12 C11 C15 120.15(15) . . ?
C10 C11 C15 117.92(15) . . ?
C11 C10 C9 118.81(15) . . ?
C11 C10 H13 120.6 . . ?
C9 C10 H13 120.6 . . ?
F6 C15 F4 106.47(15) . . ?
F6 C15 F5 106.32(15) . . ?
F4 C15 F5 105.11(15) . . ?
F6 C15 C11 113.10(15) . . ?
F4 C15 C11 113.01(14) . . ?
F5 C15 C11 112.24(14) . . ?
O1 C8 N1 127.01(14) . . ?
O1 C8 C8 121.01(17) . 2_665 ?
N1 C8 C8 111.98(16) . 2_665 ?
O2 C16 N2 127.36(15) . . ?
O2 C16 C16 121.25(17) . 2_776 ?
N2 C16 C16 111.39(16) . 2_776 ?
C8 N1 C1 126.89(13) . . ?
C8 N1 H1 116.6 . . ?
C1 N1 H1 116.6 . . ?
C16 N2 C9 128.30(13) . . ?
C16 N2 H2A 115.8 . . ?
C9 N2 H2A 115.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.4(2) . . . . ?
N1 C1 C2 C3 -177.77(15) . . . . ?
C1 C2 C3 C4 -1.2(3) . . . . ?
C1 C2 C3 C7 175.04(16) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C7 C3 C4 C5 -175.33(18) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C2 C1 C6 C5 0.6(3) . . . . ?
N1 C1 C6 C5 178.87(17) . . . . ?
C4 C5 C6 C1 -0.9(3) . . . . ?
C4 C3 C7 F1 -169.90(16) . . . . ?
C2 C3 C7 F1 13.7(2) . . . . ?
C4 C3 C7 F2 69.5(2) . . . . ?
C2 C3 C7 F2 -106.94(19) . . . . ?
C4 C3 C7 F3 -48.9(2) . . . . ?
C2 C3 C7 F3 134.73(17) . . . . ?
C10 C9 C14 C13 -1.0(3) . . . . ?
N2 C9 C14 C13 179.45(16) . . . . ?
C9 C14 C13 C12 0.1(3) . . . . ?
C14 C13 C12 C11 0.7(3) . . . . ?
C13 C12 C11 C10 -0.8(3) . . . . ?
C13 C12 C11 C15 -179.18(16) . . . . ?
C12 C11 C10 C9 0.0(2) . . . . ?
C15 C11 C10 C9 178.39(15) . . . . ?
C14 C9 C10 C11 0.9(2) . . . . ?
N2 C9 C10 C11 -179.53(15) . . . . ?
C12 C11 C15 F6 -24.6(2) . . . . ?
C10 C11 C15 F6 156.95(16) . . . . ?
C12 C11 C15 F4 -145.65(16) . . . . ?
C10 C11 C15 F4 35.9(2) . . . . ?
C12 C11 C15 F5 95.69(19) . . . . ?
C10 C11 C15 F5 -82.76(19) . . . . ?
O1 C8 N1 C1 4.1(3) . . . . ?
C8 C8 N1 C1 -175.52(16) 2_665 . . . ?
C6 C1 N1 C8 148.59(17) . . . . ?
C2 C1 N1 C8 -33.2(3) . . . . ?
O2 C16 N2 C9 -3.8(3) . . . . ?
C16 C16 N2 C9 176.64(16) 2_776 . . . ?
C10 C9 N2 C16 0.9(3) . . . . ?
C14 C9 N2 C16 -179.52(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2 O1 0.95 2.45 2.9520(19) 112.7 . yes
N1 H1 O1 0.88 2.15 2.8814(17) 140.4 1_455 yes
N2 H2A F3 0.88 2.36 3.2051(17) 160.9 2_676 yes
N2 H2A O2 0.88 2.23 2.6675(18) 110.1 2_776 yes

_refine_diff_density_max         0.580
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.064

