# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1834749'
loop_
_audit_author_name
_audit_author_address
'wang rui'
;Northeast university 
China
;
_audit_update_record             
;
2018-04-04 deposited with the CCDC.	2019-09-05 downloaded from the CCDC.
;
_audit_creation_date             2018-04-04
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H12 F7 N3 O'
_chemical_formula_sum            'C9 H12 F7 N3 O'
_chemical_formula_weight         311.22
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

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

_cell_length_a                   11.7613(10)
_cell_length_b                   7.2600(4)
_cell_length_c                   15.9064(13)
_cell_angle_alpha                90
_cell_angle_beta                 101.506(4)
_cell_angle_gamma                90
_cell_volume                     1330.91(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3471
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.82
_cell_measurement_theta_min      3.10
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0859
_diffrn_reflns_av_unetI/netI     0.0730
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12981
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.743
_diffrn_reflns_theta_min         2.398
_diffrn_ambient_temperature      296.58
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1684
_reflns_number_total             2523
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.109
_refine_ls_extinction_coef       0.13(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.566
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2523
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1570
_refine_ls_R_factor_gt           0.1231
_refine_ls_restrained_S_all      1.566
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3689
_refine_ls_wR_factor_ref         0.4095
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Me refined with riding coordinates:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.7550(5) 0.6486(4) 0.5024(2) 0.1221(19) Uani 1 1 d . . . . .
F2 F 0.6117(3) 0.4849(6) 0.4418(3) 0.1083(16) Uani 1 1 d . . . . .
F3 F 0.9013(4) 0.3881(9) 0.4455(4) 0.159(2) Uani 1 1 d . . . . .
F4 F 0.7469(6) 0.2649(6) 0.3742(3) 0.156(3) Uani 1 1 d . . . . .
F5 F 0.8443(7) 0.4970(11) 0.2810(4) 0.188(3) Uani 1 1 d . . . . .
F6 F 0.8342(9) 0.7116(9) 0.3621(4) 0.218(4) Uani 1 1 d . . . . .
F7 F 0.6855(6) 0.5920(10) 0.2965(4) 0.185(3) Uani 1 1 d . . . . .
C1 C 0.8470(5) -0.1148(7) 0.7102(4) 0.0803(17) Uani 1 1 d . . . . .
H1A H 0.9252 -0.1589 0.7165 0.120 Uiso 1 1 calc R . . . .
H1B H 0.8422 -0.0303 0.7558 0.120 Uiso 1 1 calc R . . . .
H1C H 0.7958 -0.2169 0.7124 0.120 Uiso 1 1 calc R . . . .
C2 C 0.9020(5) 0.0089(8) 0.5784(5) 0.0858(19) Uani 1 1 d . . . . .
H2A H 0.9720 -0.0534 0.6049 0.129 Uiso 1 1 calc R . . . .
H2B H 0.8757 -0.0382 0.5215 0.129 Uiso 1 1 calc R . . . .
H2C H 0.9169 0.1385 0.5757 0.129 Uiso 1 1 calc R . . . .
C3 C 0.6036(5) -0.1974(7) 0.6569(4) 0.0807(17) Uani 1 1 d . . . . .
H3A H 0.5305 -0.2105 0.6743 0.121 Uiso 1 1 calc R . . . .
H3B H 0.6065 -0.2798 0.6101 0.121 Uiso 1 1 calc R . . . .
H3C H 0.6654 -0.2264 0.7043 0.121 Uiso 1 1 calc R . . . .
C4 C 0.5093(5) 0.1033(9) 0.6157(4) 0.0774(16) Uani 1 1 d . . . . .
H4A H 0.4518 0.0390 0.6395 0.116 Uiso 1 1 calc R . . . .
H4B H 0.5247 0.2207 0.6434 0.116 Uiso 1 1 calc R . . . .
H4C H 0.4813 0.1214 0.5553 0.116 Uiso 1 1 calc R . . . .
C5 C 0.7076(4) 0.0551(5) 0.6017(3) 0.0481(11) Uani 1 1 d . . . . .
C6 C 0.7471(4) 0.3470(6) 0.5578(3) 0.0549(12) Uani 1 1 d . . . . .
C7 C 0.7266(5) 0.4752(6) 0.4783(3) 0.0641(14) Uani 1 1 d . . . . .
C8 C 0.7895(6) 0.4253(8) 0.4095(4) 0.0784(16) Uani 1 1 d . . . . .
C9 C 0.7915(8) 0.5567(11) 0.3355(5) 0.100(2) Uani 1 1 d . . . . .
N1 N 0.8135(3) -0.0219(5) 0.6286(3) 0.0588(11) Uani 1 1 d . . . . .
N2 N 0.6168(3) -0.0058(5) 0.6291(2) 0.0581(11) Uani 1 1 d . . . . .
N3 N 0.6920(3) 0.1914(5) 0.5417(2) 0.0565(11) Uani 1 1 d . . . . .
O1 O 0.8076(4) 0.4070(5) 0.6233(2) 0.0850(14) 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 C7 1.338(5) . ?
F2 C7 1.362(6) . ?
F3 C8 1.353(7) . ?
F4 C8 1.346(7) . ?
F5 C9 1.240(9) . ?
F6 C9 1.269(9) . ?
F7 C9 1.302(10) . ?
C1 N1 1.445(7) . ?
C2 N1 1.450(7) . ?
C3 N2 1.476(6) . ?
C4 N2 1.471(6) . ?
C5 N1 1.354(5) . ?
C5 N2 1.308(5) . ?
C5 N3 1.362(5) . ?
C6 C7 1.549(7) . ?
C6 N3 1.302(5) . ?
C6 O1 1.219(6) . ?
C7 C8 1.483(8) . ?
C8 C9 1.518(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C5 N3 120.5(4) . . ?
N2 C5 N1 121.1(4) . . ?
N2 C5 N3 118.3(4) . . ?
N3 C6 C7 111.7(4) . . ?
O1 C6 C7 116.9(4) . . ?
O1 C6 N3 131.3(4) . . ?
F1 C7 F2 104.1(4) . . ?
F1 C7 C6 110.0(4) . . ?
F1 C7 C8 108.0(4) . . ?
F2 C7 C6 111.0(4) . . ?
F2 C7 C8 107.2(5) . . ?
C8 C7 C6 115.9(4) . . ?
F3 C8 C7 108.8(5) . . ?
F3 C8 C9 106.8(6) . . ?
F4 C8 F3 104.7(6) . . ?
F4 C8 C7 108.7(5) . . ?
F4 C8 C9 106.4(5) . . ?
C7 C8 C9 120.4(5) . . ?
F5 C9 F6 108.8(8) . . ?
F5 C9 F7 107.5(8) . . ?
F5 C9 C8 114.1(7) . . ?
F6 C9 F7 105.2(9) . . ?
F6 C9 C8 111.4(7) . . ?
F7 C9 C8 109.3(6) . . ?
C1 N1 C2 118.0(5) . . ?
C5 N1 C1 123.0(4) . . ?
C5 N1 C2 118.6(4) . . ?
C4 N2 C3 114.4(5) . . ?
C5 N2 C3 124.0(4) . . ?
C5 N2 C4 120.3(4) . . ?
C6 N3 C5 120.0(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_test
_database_code_depnum_ccdc_archive 'CCDC 1841627'
loop_
_audit_author_name
_audit_author_address
'wang rui'
;Northeast university 
China
;
_audit_update_record             
;
2018-05-06 deposited with the CCDC.	2019-09-05 downloaded from the CCDC.
;
_audit_creation_date             2018-05-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H8 F7 N3 O'
_chemical_formula_sum            'C7 H8 F7 N3 O'
_chemical_formula_weight         283.16
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.986(18)
_cell_length_b                   9.949(16)
_cell_length_c                   10.414(17)
_cell_angle_alpha                90
_cell_angle_beta                 98.87(2)
_cell_angle_gamma                90
_cell_volume                     1125(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293
_cell_measurement_reflns_used    1763
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.5
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.672
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    "'not measured'"
_exptl_crystal_description       Prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0654
_diffrn_reflns_av_unetI/netI     0.0610
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8201
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.645
_diffrn_reflns_theta_min         3.239
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1213
_reflns_number_total             2594
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2594
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1485
_refine_ls_R_factor_gt           0.0681
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1687
_refine_ls_wR_factor_ref         0.2164
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(F6A)=1-FVAR(1)
 Sof(F6)=FVAR(1)
3.a X=CH2 refined with riding coordinates:
 N2(H2D,H2E)
3.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2263(5) -0.2963(5) -0.4620(5) 0.0921(15) Uani 1 1 d . . . . .
H1A H 0.252557 -0.261506 -0.376247 0.138 Uiso 1 1 calc GR . . . .
H1B H 0.209929 -0.390791 -0.456879 0.138 Uiso 1 1 calc GR . . . .
H1C H 0.152733 -0.250710 -0.500783 0.138 Uiso 1 1 calc GR . . . .
C2 C 0.3709(4) -0.1409(4) -0.5471(5) 0.0836(13) Uani 1 1 d . . . . .
H2A H 0.327853 -0.081205 -0.497245 0.125 Uiso 1 1 calc GR . . . .
H2B H 0.360025 -0.111443 -0.635893 0.125 Uiso 1 1 calc GR . . . .
H2C H 0.457081 -0.140651 -0.512178 0.125 Uiso 1 1 calc GR . . . .
C3 C 0.3675(3) -0.3772(3) -0.6038(3) 0.0517(8) Uani 1 1 d . . . . .
C4 C 0.3531(3) -0.6029(3) -0.6552(4) 0.0564(9) Uani 1 1 d . . . . .
C5 C 0.2791(3) -0.7302(3) -0.6334(4) 0.0583(9) Uani 1 1 d . . . . .
C6 C 0.1403(4) -0.7223(3) -0.6865(4) 0.0608(9) Uani 1 1 d . . . . .
C7 C 0.0696(4) -0.8551(5) -0.7069(5) 0.0803(13) Uani 1 1 d . . . . .
F1 F 0.2914(2) -0.7620(3) -0.5077(2) 0.0937(9) Uani 1 1 d . . . . .
F2 F 0.3230(2) -0.83675(19) -0.6948(3) 0.0930(9) Uani 1 1 d . . . . .
F3 F 0.0836(2) -0.6487(2) -0.6053(3) 0.0880(8) Uani 1 1 d . . . . .
F4 F 0.1259(2) -0.6573(3) -0.8016(2) 0.0924(8) Uani 1 1 d . . . . .
F5 F 0.0881(3) -0.9275(3) -0.6010(4) 0.1239(12) Uani 1 1 d . . . . .
F6 F 0.105(2) -0.912(4) -0.811(3) 0.133(7) Uani 0.50(15) 1 d . . P A 1
F7 F -0.0498(3) -0.8326(3) -0.7359(3) 0.1193(11) Uani 1 1 d . . . . .
N1 N 0.3227(3) -0.2751(3) -0.5409(3) 0.0620(8) Uani 1 1 d . . . . .
N2 N 0.4565(3) -0.3548(3) -0.6743(3) 0.0676(9) Uani 1 1 d . . . . .
H2D H 0.485327 -0.275013 -0.679686 0.081 Uiso 1 1 calc R . . . .
H2E H 0.485238 -0.420204 -0.714618 0.081 Uiso 1 1 calc R . . . .
N3 N 0.3158(3) -0.4993(3) -0.5936(3) 0.0549(7) Uani 1 1 d . . . . .
O1 O 0.4343(3) -0.6155(2) -0.7266(3) 0.0816(9) Uani 1 1 d . . . . .
F6A F 0.1035(15) -0.936(4) -0.791(5) 0.125(8) Uani 0.50(15) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 N1 1.452(5) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C2 N1 1.442(5) . ?
C3 N1 1.343(4) . ?
C3 N2 1.329(4) . ?
C3 N3 1.352(4) . ?
C4 C5 1.540(5) . ?
C4 N3 1.313(4) . ?
C4 O1 1.253(4) . ?
C5 C6 1.543(6) . ?
C5 F1 1.332(5) . ?
C5 F2 1.364(4) . ?
C6 C7 1.530(6) . ?
C6 F3 1.342(4) . ?
C6 F4 1.350(5) . ?
C7 F5 1.306(6) . ?
C7 F6 1.33(2) . ?
C7 F7 1.319(6) . ?
C7 F6A 1.29(2) . ?
N2 H2D 0.8600 . ?
N2 H2E 0.8600 . ?

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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
N1 C3 N3 116.8(3) . . ?
N2 C3 N1 120.0(3) . . ?
N2 C3 N3 123.2(3) . . ?
N3 C4 C5 111.3(3) . . ?
O1 C4 C5 116.4(3) . . ?
O1 C4 N3 132.3(3) . . ?
C4 C5 C6 114.8(3) . . ?
F1 C5 C4 111.3(3) . . ?
F1 C5 C6 108.0(3) . . ?
F1 C5 F2 106.7(3) . . ?
F2 C5 C4 109.7(3) . . ?
F2 C5 C6 105.8(3) . . ?
C7 C6 C5 117.3(3) . . ?
F3 C6 C5 109.3(3) . . ?
F3 C6 C7 106.5(3) . . ?
F3 C6 F4 107.2(3) . . ?
F4 C6 C5 108.5(3) . . ?
F4 C6 C7 107.6(4) . . ?
F5 C7 C6 110.4(4) . . ?
F5 C7 F6 115(2) . . ?
F5 C7 F7 107.9(4) . . ?
F6 C7 C6 106.3(18) . . ?
F7 C7 C6 110.5(4) . . ?
F7 C7 F6 106.7(11) . . ?
F6A C7 C6 116(2) . . ?
F6A C7 F5 102(3) . . ?
F6A C7 F7 109.4(11) . . ?
C2 N1 C1 117.7(3) . . ?
C3 N1 C1 121.4(3) . . ?
C3 N1 C2 120.9(3) . . ?
C3 N2 H2D 120.0 . . ?
C3 N2 H2E 120.0 . . ?
H2D N2 H2E 120.0 . . ?
C4 N3 C3 120.1(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
C4 C5 C6 C7 161.4(4) . . . . ?
C4 C5 C6 F3 -77.3(4) . . . . ?
C4 C5 C6 F4 39.3(4) . . . . ?
C5 C4 N3 C3 -178.2(3) . . . . ?
C5 C6 C7 F5 52.5(5) . . . . ?
C5 C6 C7 F6 -72.8(17) . . . . ?
C5 C6 C7 F7 171.7(4) . . . . ?
C5 C6 C7 F6A -63(2) . . . . ?
F1 C5 C6 C7 -73.7(4) . . . . ?
F1 C5 C6 F3 47.6(4) . . . . ?
F1 C5 C6 F4 164.2(3) . . . . ?
F2 C5 C6 C7 40.3(5) . . . . ?
F2 C5 C6 F3 161.6(3) . . . . ?
F2 C5 C6 F4 -81.8(4) . . . . ?
F3 C6 C7 F5 -70.3(5) . . . . ?
F3 C6 C7 F6 164.4(16) . . . . ?
F3 C6 C7 F7 49.0(5) . . . . ?
F3 C6 C7 F6A 174(2) . . . . ?
F4 C6 C7 F5 175.0(4) . . . . ?
F4 C6 C7 F6 49.7(16) . . . . ?
F4 C6 C7 F7 -65.7(5) . . . . ?
F4 C6 C7 F6A 60(2) . . . . ?
N1 C3 N3 C4 178.3(3) . . . . ?
N2 C3 N1 C1 -179.4(4) . . . . ?
N2 C3 N1 C2 -0.9(5) . . . . ?
N2 C3 N3 C4 0.0(5) . . . . ?
N3 C3 N1 C1 2.2(5) . . . . ?
N3 C3 N1 C2 -179.3(3) . . . . ?
N3 C4 C5 C6 63.1(4) . . . . ?
N3 C4 C5 F1 -60.0(4) . . . . ?
N3 C4 C5 F2 -177.9(3) . . . . ?
O1 C4 C5 C6 -116.4(4) . . . . ?
O1 C4 C5 F1 120.5(4) . . . . ?
O1 C4 C5 F2 2.7(5) . . . . ?
O1 C4 N3 C3 1.1(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
