# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_x_a
_database_code_depnum_ccdc_archive 'CCDC 2088784'
loop_
_audit_author_name
_audit_author_address
'Chun-Jiang Wang'
;Wuhan University
China
;
_audit_update_record             
;
2021-06-08 deposited with the CCDC.	2021-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H17 F3 N2 O2'
_chemical_formula_weight         314.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   8.6836(12)
_cell_length_b                   9.4176(13)
_cell_length_c                   19.321(3)
_cell_angle_alpha                83.076(3)
_cell_angle_beta                 83.623(3)
_cell_angle_gamma                89.078(3)
_cell_volume                     1558.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4725
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      26.58

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.113
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6760
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS-2012/1 (Bruker,2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa APEX-Duo CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20868
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.068
_diffrn_reflns_theta_max         28.312
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             7582
_reflns_number_gt                4504
_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    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0763P)²+0.6887P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7582
_refine_ls_number_parameters     495
_refine_ls_number_restraints     41
_refine_ls_R_factor_all          0.1089
_refine_ls_R_factor_gt           0.0620
_refine_ls_wR_factor_ref         0.1864
_refine_ls_wR_factor_gt          0.1591
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.017
_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 0.6568(3) 0.0800(3) 1.13813(12) 0.1335(10) Uani 1 1 d . . . . .
H1 H 0.952(3) 0.221(3) 0.7714(15) 0.073(9) Uiso 1 1 d . . . . .
O1 O 0.6405(2) 0.54645(19) 0.91871(9) 0.0596(5) Uani 1 1 d . . . . .
N1 N 0.7821(2) 0.3931(2) 0.85251(10) 0.0497(5) Uani 1 1 d . . . . .
C1 C 0.8816(3) 0.1707(4) 0.80298(15) 0.0643(8) Uani 1 1 d . . . . .
F2 F 0.6542(3) 0.2976(3) 1.14745(10) 0.1199(9) Uani 1 1 d . . . . .
H2N H 0.556(3) 0.321(3) 1.0372(13) 0.046(7) Uiso 1 1 d . . . . .
H2 H 0.934(4) -0.032(4) 0.7781(19) 0.105(11) Uiso 1 1 d . . . . .
O2 O 0.8549(2) 0.3450(3) 1.01667(12) 0.0826(7) Uani 1 1 d . . . . .
N2 N 0.6009(2) 0.2591(2) 1.01436(9) 0.0428(4) Uani 1 1 d . . . . .
C2 C 0.8650(4) 0.0261(4) 0.80931(17) 0.0766(9) Uani 1 1 d . . . . .
C3 C 0.7578(4) -0.0453(4) 0.85957(17) 0.0744(9) Uani 1 1 d . . . . .
H3 H 0.747(3) -0.146(3) 0.8632(16) 0.082(10) Uiso 1 1 d . . . . .
F3 F 0.8665(2) 0.1871(3) 1.14199(10) 0.1061(7) Uani 1 1 d . . . . .
N3 N 0.2947(2) 0.1749(2) 0.35465(9) 0.0445(4) Uani 1 1 d . . . . .
O3 O 0.15330(18) -0.01101(17) 0.41754(9) 0.0510(4) Uani 1 1 d . . . . .
F5 F 0.1649(3) 0.0998(2) 0.64561(9) 0.1051(7) Uani 1 1 d . . . . .
C5 C 0.6779(2) 0.1757(3) 0.89891(11) 0.0446(5) Uani 1 1 d . . . . .
C4 C 0.6622(3) 0.0301(3) 0.90442(14) 0.0552(6) Uani 1 1 d . . . . .
H4 H 0.595(3) -0.016(3) 0.9379(14) 0.060(8) Uiso 1 1 d . . . . .
H4N H 0.056(2) 0.146(2) 0.5343(11) 0.036(6) Uiso 1 1 d . . . . .
F4 F 0.1375(2) 0.3219(2) 0.64510(9) 0.0999(7) Uani 1 1 d . . . . .
N4 N 0.09932(19) 0.2247(2) 0.51499(9) 0.0367(4) Uani 1 1 d . . . . .
O4 O 0.35813(17) 0.1434(2) 0.51563(10) 0.0614(5) Uani 1 1 d . . . . .
C6 C 0.5910(2) 0.2850(2) 0.93859(11) 0.0411(5) Uani 1 1 d . . . . .
F6 F 0.3615(2) 0.2288(2) 0.64443(9) 0.0918(6) Uani 1 1 d . . . . .
C7 C 0.6713(2) 0.4261(3) 0.90389(12) 0.0453(5) Uani 1 1 d . . . . .
C8 C 0.8870(4) 0.4978(4) 0.81243(18) 0.0688(8) Uani 1 1 d . . . . .
H8C H 0.897(4) 0.496(4) 0.765(2) 0.113(13) Uiso 1 1 d . . . . .
H8A H 0.852(3) 0.594(3) 0.8207(15) 0.071(9) Uiso 1 1 d . . . . .
H8B H 0.989(4) 0.488(4) 0.8272(17) 0.098(11) Uiso 1 1 d . . . . .
C9 C 0.4164(3) 0.2938(3) 0.92907(13) 0.0515(6) Uani 1 1 d D . . . .
H9B H 0.367(3) 0.364(3) 0.9569(14) 0.064(8) Uiso 1 1 d . . . . .
H9A H 0.376(3) 0.202(3) 0.9487(13) 0.052(7) Uiso 1 1 d . . . . .
C00I C 0.2961(2) 0.3245(2) 0.35252(11) 0.0422(5) Uani 1 1 d . . . . .
C00O C 0.7873(2) 0.2451(3) 0.84873(11) 0.0469(5) Uani 1 1 d . . . . .
C14 C 1.0122(3) 0.2998(6) 0.9966(2) 0.1272(18) Uani 1 1 d . . . . .
H14A H 1.010201 0.216586 0.972521 0.191 Uiso 1 1 calc R U . . .
H14B H 1.064471 0.277368 1.037841 0.191 Uiso 1 1 calc R U . . .
H14C H 1.066149 0.375524 0.966212 0.191 Uiso 1 1 calc R U . . .
C10A C 0.3833(10) 0.3438(8) 0.8556(3) 0.0574(18) Uani 0.674(11) 1 d D U P A 1
H10A H 0.427689 0.429312 0.833934 0.069 Uiso 0.674(11) 1 calc R U P A 1
C11A C 0.2976(6) 0.2761(10) 0.8210(3) 0.079(2) Uani 0.674(11) 1 d D U P A 1
H11A H 0.251630 0.190290 0.841287 0.095 Uiso 0.674(11) 1 calc R U P A 1
H11B H 0.281269 0.312595 0.775449 0.095 Uiso 0.674(11) 1 calc R U P A 1
C10B C 0.3829(18) 0.2827(14) 0.8534(6) 0.047(3) Uani 0.326(11) 1 d D U P A 2
H10B H 0.421544 0.206822 0.830030 0.057 Uiso 0.326(11) 1 calc R U P A 2
C11B C 0.2989(11) 0.3824(15) 0.8229(5) 0.064(3) Uani 0.326(11) 1 d D U P A 2
H11C H 0.260945 0.457743 0.846881 0.077 Uiso 0.326(11) 1 calc R U P A 2
H11D H 0.277063 0.378069 0.777179 0.077 Uiso 0.326(11) 1 calc R U P A 2
C13 C 0.7318(3) 0.2003(3) 1.11612(15) 0.0621(7) Uani 1 1 d . . . . .
C12 C 0.7498(3) 0.2313(3) 1.03664(12) 0.0496(6) Uani 1 1 d . . . . .
H12 H 0.808(3) 0.145(2) 1.0173(12) 0.045(6) Uiso 1 1 d . . . . .
C16 C 0.3688(3) 0.5661(3) 0.31783(14) 0.0618(7) Uani 1 1 d . . . . .
H16 H 0.427(3) 0.641(3) 0.2880(15) 0.076(9) Uiso 1 1 d . . . . .
C17 C 0.2551(3) 0.6109(3) 0.36585(14) 0.0580(7) Uani 1 1 d . . . . .
H17 H 0.241(3) 0.709(3) 0.3692(13) 0.062(8) Uiso 1 1 d . . . . .
C18 C 0.1599(3) 0.5107(3) 0.40838(12) 0.0470(5) Uani 1 1 d . . . . .
H18 H 0.076(3) 0.548(3) 0.4420(14) 0.064(8) Uiso 1 1 d . . . . .
C19 C 0.1805(2) 0.3685(2) 0.40151(10) 0.0379(5) Uani 1 1 d . . . . .
C20 C 0.0944(2) 0.2388(2) 0.43897(10) 0.0353(4) Uani 1 1 d . . . . .
C21 C 0.1817(2) 0.1161(2) 0.40431(11) 0.0397(5) Uani 1 1 d . . . . .
C22 C 0.4053(3) 0.0917(3) 0.31437(15) 0.0657(7) Uani 1 1 d . . . . .
H22A H 0.404122 0.122993 0.265272 0.099 Uiso 1 1 calc R U . . .
H22B H 0.377897 -0.007669 0.323704 0.099 Uiso 1 1 calc R U . . .
H22C H 0.507157 0.104592 0.327454 0.099 Uiso 1 1 calc R U . . .
C23 C -0.0771(2) 0.2363(3) 0.42580(12) 0.0430(5) Uani 1 1 d . . . . .
H23B H -0.132(3) 0.316(2) 0.4460(12) 0.044(6) Uiso 1 1 d . . . . .
H23A H -0.120(3) 0.147(3) 0.4530(13) 0.051(6) Uiso 1 1 d . . . . .
C24 C -0.1026(3) 0.2435(3) 0.35049(13) 0.0570(6) Uani 1 1 d . . . . .
H24 H -0.051944 0.175026 0.325349 0.068 Uiso 1 1 calc R U . . .
C25 C -0.1862(4) 0.3333(4) 0.31689(17) 0.0848(10) Uani 1 1 d . . . . .
H25A H -0.239442 0.404079 0.339553 0.102 Uiso 1 1 calc R U . . .
H25B H -0.194187 0.328215 0.269651 0.102 Uiso 1 1 calc R U . . .
C26 C 0.2464(2) 0.2414(3) 0.53898(12) 0.0428(5) Uani 1 1 d . . . . .
H26 H 0.279(2) 0.335(2) 0.5268(11) 0.036(6) Uiso 1 1 d . . . . .
C27 C 0.2268(3) 0.2225(3) 0.61847(13) 0.0548(6) Uani 1 1 d . . . . .
C28 C 0.5127(3) 0.1980(4) 0.49810(18) 0.0892(11) Uani 1 1 d . . . . .
H28A H 0.574483 0.131813 0.472691 0.134 Uiso 1 1 calc R U . . .
H28B H 0.557156 0.210041 0.540319 0.134 Uiso 1 1 calc R U . . .
H28C H 0.509737 0.288540 0.469544 0.134 Uiso 1 1 calc R U . . .
C15 C 0.3920(3) 0.4224(3) 0.30998(13) 0.0547(6) Uani 1 1 d . . . . .
H15 H 0.470(3) 0.393(3) 0.2741(14) 0.062(7) 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
F1 C13 1.317(3) . ?
O1 C7 1.221(3) . ?
N1 C7 1.364(3) . ?
N1 C00O 1.405(3) . ?
N1 C8 1.446(3) . ?
C1 C2 1.361(5) . ?
C1 C00O 1.383(3) . ?
C1 H1 0.91(3) . ?
F2 C13 1.298(3) . ?
O2 C12 1.408(3) . ?
O2 C14 1.449(4) . ?
N2 C12 1.418(3) . ?
N2 C6 1.467(3) . ?
N2 H2N 0.84(2) . ?
C2 C3 1.387(5) . ?
C2 H2 1.00(4) . ?
C3 C4 1.383(4) . ?
C3 H3 0.95(3) . ?
F3 C13 1.321(3) . ?
N3 C21 1.367(3) . ?
N3 C00I 1.404(3) . ?
N3 C22 1.449(3) . ?
O3 C21 1.217(3) . ?
F5 C27 1.308(3) . ?
C5 C4 1.371(4) . ?
C5 C00O 1.390(3) . ?
C5 C6 1.501(3) . ?
C4 H4 0.90(3) . ?
F4 C27 1.321(3) . ?
N4 C26 1.424(3) . ?
N4 C20 1.464(3) . ?
N4 H4N 0.86(2) . ?
O4 C26 1.404(3) . ?
O4 C28 1.435(3) . ?
C6 C9 1.547(3) . ?
C6 C7 1.553(3) . ?
F6 C27 1.328(3) . ?
C8 H8C 0.91(4) . ?
C8 H8A 0.98(3) . ?
C8 H8B 0.96(4) . ?
C9 C10A 1.497(7) . ?
C9 C10B 1.537(11) . ?
C9 H9B 0.97(3) . ?
C9 H9A 0.96(3) . ?
C00I C15 1.382(3) . ?
C00I C19 1.395(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C13 C12 1.519(4) . ?
C12 H12 1.04(2) . ?
C16 C17 1.375(4) . ?
C16 C15 1.389(4) . ?
C16 H16 0.96(3) . ?
C17 C18 1.391(3) . ?
C17 H17 0.94(3) . ?
C18 C19 1.369(3) . ?
C18 H18 1.01(3) . ?
C19 C20 1.507(3) . ?
C20 C23 1.539(3) . ?
C20 C21 1.550(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.489(3) . ?
C23 H23B 0.98(2) . ?
C23 H23A 0.99(2) . ?
C24 C25 1.271(4) . ?
C24 H24 0.9300 . ?
C25 H25A 0.9300 . ?
C25 H25B 0.9300 . ?
C26 C27 1.515(3) . ?
C26 H26 0.93(2) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C15 H15 0.98(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C00O 110.93(18) . . ?
C7 N1 C8 123.1(2) . . ?
C00O N1 C8 125.7(2) . . ?
C2 C1 C00O 117.5(3) . . ?
C2 C1 H1 124.2(18) . . ?
C00O C1 H1 118.3(19) . . ?
C12 O2 C14 114.0(3) . . ?
C12 N2 C6 117.34(17) . . ?
C12 N2 H2N 109.4(16) . . ?
C6 N2 H2N 114.1(16) . . ?
C1 C2 C3 121.8(3) . . ?
C1 C2 H2 120(2) . . ?
C3 C2 H2 118(2) . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 118.9(19) . . ?
C2 C3 H3 120.8(19) . . ?
C21 N3 C00I 110.84(17) . . ?
C21 N3 C22 123.8(2) . . ?
C00I N3 C22 125.16(19) . . ?
C4 C5 C00O 120.1(2) . . ?
C4 C5 C6 130.9(2) . . ?
C00O C5 C6 109.0(2) . . ?
C5 C4 C3 118.6(3) . . ?
C5 C4 H4 120.7(17) . . ?
C3 C4 H4 120.6(17) . . ?
C26 N4 C20 116.91(16) . . ?
C26 N4 H4N 111.2(14) . . ?
C20 N4 H4N 110.1(14) . . ?
C26 O4 C28 115.7(2) . . ?
N2 C6 C5 112.83(18) . . ?
N2 C6 C9 106.44(16) . . ?
C5 C6 C9 113.7(2) . . ?
N2 C6 C7 112.88(18) . . ?
C5 C6 C7 101.82(16) . . ?
C9 C6 C7 109.28(19) . . ?
O1 C7 N1 125.3(2) . . ?
O1 C7 C6 126.6(2) . . ?
N1 C7 C6 108.1(2) . . ?
N1 C8 H8C 116(2) . . ?
N1 C8 H8A 110.0(17) . . ?
H8C C8 H8A 106(3) . . ?
N1 C8 H8B 111(2) . . ?
H8C C8 H8B 107(3) . . ?
H8A C8 H8B 106(3) . . ?
C6 C9 H9B 109.6(16) . . ?
C6 C9 H9A 104.7(14) . . ?
H9B C9 H9A 108(2) . . ?
C15 C00I C19 121.2(2) . . ?
C15 C00I N3 128.7(2) . . ?
C19 C00I N3 110.13(18) . . ?
C1 C00O C5 121.6(3) . . ?
C1 C00O N1 128.2(2) . . ?
C5 C00O N1 110.15(19) . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
F2 C13 F1 105.3(3) . . ?
F2 C13 F3 106.8(2) . . ?
F1 C13 F3 106.2(2) . . ?
F2 C13 C12 113.7(2) . . ?
F1 C13 C12 112.0(2) . . ?
F3 C13 C12 112.4(2) . . ?
O2 C12 N2 113.9(2) . . ?
O2 C12 C13 108.5(2) . . ?
N2 C12 C13 108.38(19) . . ?
O2 C12 H12 103.7(12) . . ?
N2 C12 H12 115.0(12) . . ?
C13 C12 H12 107.0(12) . . ?
C17 C16 C15 121.9(2) . . ?
C17 C16 H16 115.9(17) . . ?
C15 C16 H16 122.1(17) . . ?
C16 C17 C18 119.9(3) . . ?
C16 C17 H17 119.9(16) . . ?
C18 C17 H17 120.2(16) . . ?
C19 C18 C17 119.3(2) . . ?
C19 C18 H18 123.4(15) . . ?
C17 C18 H18 117.3(15) . . ?
C18 C19 C00I 120.3(2) . . ?
C18 C19 C20 130.75(19) . . ?
C00I C19 C20 108.92(18) . . ?
N4 C20 C19 112.57(17) . . ?
N4 C20 C23 107.45(15) . . ?
C19 C20 C23 113.50(17) . . ?
N4 C20 C21 112.63(16) . . ?
C19 C20 C21 101.66(15) . . ?
C23 C20 C21 109.03(17) . . ?
O3 C21 N3 125.3(2) . . ?
O3 C21 C20 126.25(18) . . ?
N3 C21 C20 108.43(18) . . ?
N3 C22 H22A 109.5 . . ?
N3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C20 114.37(18) . . ?
C24 C23 H23B 109.0(13) . . ?
C20 C23 H23B 109.6(13) . . ?
C24 C23 H23A 111.5(14) . . ?
C20 C23 H23A 105.5(13) . . ?
H23B C23 H23A 106.6(19) . . ?
C25 C24 C23 127.0(3) . . ?
C25 C24 H24 116.5 . . ?
C23 C24 H24 116.5 . . ?
C24 C25 H25A 120.0 . . ?
C24 C25 H25B 120.0 . . ?
H25A C25 H25B 120.0 . . ?
O4 C26 N4 113.41(18) . . ?
O4 C26 C27 108.70(19) . . ?
N4 C26 C27 108.66(18) . . ?
O4 C26 H26 112.1(13) . . ?
N4 C26 H26 109.2(13) . . ?
C27 C26 H26 104.4(13) . . ?
F5 C27 F4 106.0(2) . . ?
F5 C27 F6 106.2(2) . . ?
F4 C27 F6 106.3(2) . . ?
F5 C27 C26 113.2(2) . . ?
F4 C27 C26 112.8(2) . . ?
F6 C27 C26 111.8(2) . . ?
O4 C28 H28A 109.5 . . ?
O4 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O4 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C00I C15 C16 117.5(2) . . ?
C00I C15 H15 121.8(16) . . ?
C16 C15 H15 120.6(16) . . ?

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
C00O C1 C2 C3 0.0(5) . . . . ?
C1 C2 C3 C4 1.0(5) . . . . ?
C00O C5 C4 C3 0.4(4) . . . . ?
C6 C5 C4 C3 178.9(2) . . . . ?
C2 C3 C4 C5 -1.2(4) . . . . ?
C12 N2 C6 C5 48.0(3) . . . . ?
C12 N2 C6 C9 173.3(2) . . . . ?
C12 N2 C6 C7 -66.8(3) . . . . ?
C4 C5 C6 N2 59.0(3) . . . . ?
C00O C5 C6 N2 -122.5(2) . . . . ?
C4 C5 C6 C9 -62.4(3) . . . . ?
C00O C5 C6 C9 116.2(2) . . . . ?
C4 C5 C6 C7 -179.8(2) . . . . ?
C00O C5 C6 C7 -1.2(2) . . . . ?
C00O N1 C7 O1 -179.6(2) . . . . ?
C8 N1 C7 O1 5.3(4) . . . . ?
C00O N1 C7 C6 -0.6(2) . . . . ?
C8 N1 C7 C6 -175.7(2) . . . . ?
N2 C6 C7 O1 -58.7(3) . . . . ?
C5 C6 C7 O1 -179.9(2) . . . . ?
C9 C6 C7 O1 59.6(3) . . . . ?
N2 C6 C7 N1 122.3(2) . . . . ?
C5 C6 C7 N1 1.1(2) . . . . ?
C9 C6 C7 N1 -119.5(2) . . . . ?
C21 N3 C00I C15 179.9(2) . . . . ?
C22 N3 C00I C15 4.9(4) . . . . ?
C21 N3 C00I C19 -0.5(2) . . . . ?
C22 N3 C00I C19 -175.6(2) . . . . ?
C2 C1 C00O C5 -0.8(4) . . . . ?
C2 C1 C00O N1 -179.8(2) . . . . ?
C4 C5 C00O C1 0.6(4) . . . . ?
C6 C5 C00O C1 -178.2(2) . . . . ?
C4 C5 C00O N1 179.7(2) . . . . ?
C6 C5 C00O N1 1.0(2) . . . . ?
C7 N1 C00O C1 178.8(2) . . . . ?
C8 N1 C00O C1 -6.2(4) . . . . ?
C7 N1 C00O C5 -0.2(3) . . . . ?
C8 N1 C00O C5 174.7(2) . . . . ?
C14 O2 C12 N2 -142.2(3) . . . . ?
C14 O2 C12 C13 96.9(3) . . . . ?
C6 N2 C12 O2 61.9(3) . . . . ?
C6 N2 C12 C13 -177.2(2) . . . . ?
F2 C13 C12 O2 71.9(3) . . . . ?
F1 C13 C12 O2 -169.0(2) . . . . ?
F3 C13 C12 O2 -49.6(3) . . . . ?
F2 C13 C12 N2 -52.3(3) . . . . ?
F1 C13 C12 N2 66.9(3) . . . . ?
F3 C13 C12 N2 -173.7(2) . . . . ?
C15 C16 C17 C18 0.2(4) . . . . ?
C16 C17 C18 C19 -0.3(4) . . . . ?
C17 C18 C19 C00I 0.2(3) . . . . ?
C17 C18 C19 C20 -178.8(2) . . . . ?
C15 C00I C19 C18 0.0(3) . . . . ?
N3 C00I C19 C18 -179.62(19) . . . . ?
C15 C00I C19 C20 179.2(2) . . . . ?
N3 C00I C19 C20 -0.4(2) . . . . ?
C26 N4 C20 C19 -47.1(2) . . . . ?
C26 N4 C20 C23 -172.78(19) . . . . ?
C26 N4 C20 C21 67.1(2) . . . . ?
C18 C19 C20 N4 -59.1(3) . . . . ?
C00I C19 C20 N4 121.78(18) . . . . ?
C18 C19 C20 C23 63.2(3) . . . . ?
C00I C19 C20 C23 -115.9(2) . . . . ?
C18 C19 C20 C21 -179.9(2) . . . . ?
C00I C19 C20 C21 1.0(2) . . . . ?
C00I N3 C21 O3 179.7(2) . . . . ?
C22 N3 C21 O3 -5.2(4) . . . . ?
C00I N3 C21 C20 1.2(2) . . . . ?
C22 N3 C21 C20 176.3(2) . . . . ?
N4 C20 C21 O3 59.5(3) . . . . ?
C19 C20 C21 O3 -179.8(2) . . . . ?
C23 C20 C21 O3 -59.7(3) . . . . ?
N4 C20 C21 N3 -122.03(18) . . . . ?
C19 C20 C21 N3 -1.3(2) . . . . ?
C23 C20 C21 N3 118.80(18) . . . . ?
N4 C20 C23 C24 -177.6(2) . . . . ?
C19 C20 C23 C24 57.3(3) . . . . ?
C21 C20 C23 C24 -55.2(3) . . . . ?
C20 C23 C24 C25 -125.4(3) . . . . ?
C28 O4 C26 N4 142.7(2) . . . . ?
C28 O4 C26 C27 -96.4(3) . . . . ?
C20 N4 C26 O4 -58.8(3) . . . . ?
C20 N4 C26 C27 -179.81(19) . . . . ?
O4 C26 C27 F5 -67.2(3) . . . . ?
N4 C26 C27 F5 56.6(3) . . . . ?
O4 C26 C27 F4 172.4(2) . . . . ?
N4 C26 C27 F4 -63.8(3) . . . . ?
O4 C26 C27 F6 52.6(3) . . . . ?
N4 C26 C27 F6 176.4(2) . . . . ?
C19 C00I C15 C16 0.0(3) . . . . ?
N3 C00I C15 C16 179.5(2) . . . . ?
C17 C16 C15 C00I -0.1(4) . . . . ?

_refine_diff_density_max         0.423
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.040

