# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2211108'
loop_
_audit_author_name
_audit_author_address
'Zhang gan'
;Huaibei Normal University
China
;
_audit_update_record             
;
2022-10-05 deposited with the CCDC.	2024-01-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H19 F3 N2 O2'
_chemical_formula_weight         388.38

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.150(10)
_cell_length_b                   12.826(11)
_cell_length_c                   14.113(12)
_cell_angle_alpha                70.080(15)
_cell_angle_beta                 84.051(16)
_cell_angle_gamma                76.432(15)
_cell_volume                     1844(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2038
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      24.48

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9717
_exptl_absorpt_correction_T_max  0.9814
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8798
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_sigmaI/netI    0.0767
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.54
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6330
_reflns_number_gt                2990
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0100P)²+3.3000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6330
_refine_ls_number_parameters     511
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1545
_refine_ls_R_factor_gt           0.0841
_refine_ls_wR_factor_ref         0.1917
_refine_ls_wR_factor_gt          0.1624
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.5815(4) 0.2205(4) 0.4946(3) 0.0683(13) Uani 1 1 d . . .
N2 N 0.6150(7) 0.0034(5) 0.6310(3) 0.0953(19) Uani 1 1 d . . .
N3 N 0.7975(4) 0.8809(3) 0.1234(3) 0.0574(11) Uani 1 1 d . . .
N4 N 0.7840(4) 1.0710(3) -0.0468(3) 0.0577(11) Uani 1 1 d . . .
O1 O 0.8205(5) -0.0033(4) 0.6208(3) 0.1031(15) Uani 1 1 d . . .
O2 O 0.7393(4) 0.4950(3) 0.4901(3) 0.0982(14) Uani 1 1 d . . .
O3 O 0.6874(3) 0.9881(3) -0.1239(3) 0.0728(10) Uani 1 1 d . . .
O4 O 0.5025(3) 0.7107(3) 0.2701(3) 0.0726(10) Uani 1 1 d . . .
C1 C 0.3958(9) 0.0099(8) 0.6282(6) 0.125(4) Uani 1 1 d . . .
H1 H 0.4041 -0.0632 0.6740 0.150 Uiso 1 1 calc R . .
C2 C 0.2843(9) 0.0695(9) 0.5905(8) 0.129(4) Uani 1 1 d . . .
H2 H 0.2160 0.0365 0.6118 0.155 Uiso 1 1 calc R . .
C3 C 0.2686(7) 0.1773(9) 0.5217(7) 0.130(3) Uani 1 1 d . . .
H3 H 0.1912 0.2157 0.4959 0.156 Uiso 1 1 calc R . .
C4 C 0.3685(6) 0.2278(6) 0.4913(5) 0.096(2) Uani 1 1 d . . .
H4 H 0.3586 0.3015 0.4464 0.115 Uiso 1 1 calc R . .
C5 C 0.4835(6) 0.1680(6) 0.5281(4) 0.0739(17) Uani 1 1 d . . .
C6 C 0.4988(7) 0.0595(6) 0.5974(5) 0.080(2) Uani 1 1 d . . .
C7 C 0.6342(8) -0.1098(6) 0.7057(4) 0.130(3) Uani 1 1 d . . .
H7A H 0.5812 -0.1084 0.7636 0.195 Uiso 1 1 calc R . .
H7B H 0.7187 -0.1337 0.7256 0.195 Uiso 1 1 calc R . .
H7C H 0.6153 -0.1620 0.6772 0.195 Uiso 1 1 calc R . .
C10 C 0.7963(5) 0.2264(5) 0.4834(4) 0.0689(15) Uani 1 1 d . . .
C11 C 0.8794(5) 0.1631(5) 0.4175(5) 0.0840(18) Uani 1 1 d . . .
H11A H 0.8993 0.0834 0.4546 0.126 Uiso 1 1 calc R . .
H11B H 0.9540 0.1912 0.3991 0.126 Uiso 1 1 calc R . .
H11C H 0.8368 0.1751 0.3577 0.126 Uiso 1 1 calc R . .
C12 C 0.8711(6) 0.2254(5) 0.5704(4) 0.098(2) Uani 1 1 d . . .
H12A H 0.8172 0.2605 0.6137 0.148 Uiso 1 1 calc R . .
H12B H 0.9352 0.2666 0.5430 0.148 Uiso 1 1 calc R . .
H12C H 0.9072 0.1484 0.6085 0.148 Uiso 1 1 calc R . .
C13 C 0.7448(5) 0.3481(4) 0.4188(4) 0.0606(14) Uani 1 1 d . . .
H13 H 0.6956 0.3478 0.3653 0.073 Uiso 1 1 calc R . .
C14 C 0.6648(5) 0.4218(5) 0.4792(4) 0.0764(16) Uani 1 1 d . . .
H14A H 0.5904 0.4667 0.4432 0.092 Uiso 1 1 calc R . .
H14B H 0.6414 0.3740 0.5448 0.092 Uiso 1 1 calc R . .
C15 C 0.8309(6) 0.4983(5) 0.4184(4) 0.0774(17) Uani 1 1 d . . .
C16 C 0.8402(5) 0.4181(5) 0.3726(4) 0.0674(15) Uani 1 1 d . . .
C17 C 0.9259(5) 0.4154(5) 0.2970(4) 0.0729(16) Uani 1 1 d . . .
H17 H 0.9333 0.3622 0.2643 0.088 Uiso 1 1 calc R . .
C18 C 1.0023(5) 0.4931(5) 0.2691(4) 0.0748(16) Uani 1 1 d . . .
C19 C 0.9923(6) 0.5694(5) 0.3176(5) 0.092(2) Uani 1 1 d . . .
H19 H 1.0453 0.6196 0.2991 0.111 Uiso 1 1 calc R . .
C20 C 0.9062(6) 0.5744(5) 0.3931(5) 0.096(2) Uani 1 1 d . . .
H20 H 0.8992 0.6274 0.4260 0.115 Uiso 1 1 calc R . .
C21 C 1.0924(8) 0.4898(8) 0.1887(7) 0.117(3) Uani 1 1 d . . .
C22 C 0.8495(4) 1.0610(4) 0.0359(4) 0.0537(12) Uani 1 1 d . . .
C23 C 0.9071(5) 1.1481(4) 0.0355(4) 0.0676(15) Uani 1 1 d . . .
H23 H 0.9024 1.2139 -0.0200 0.081 Uiso 1 1 calc R . .
C24 C 0.9705(5) 1.1331(5) 0.1197(5) 0.0777(17) Uani 1 1 d . . .
H24 H 1.0091 1.1896 0.1205 0.093 Uiso 1 1 calc R . .
C25 C 0.9782(5) 1.0363(5) 0.2026(5) 0.0714(15) Uani 1 1 d . . .
H25 H 1.0228 1.0268 0.2582 0.086 Uiso 1 1 calc R . .
C26 C 0.9194(5) 0.9551(5) 0.2018(4) 0.0687(15) Uani 1 1 d . . .
H26 H 0.9226 0.8905 0.2582 0.082 Uiso 1 1 calc R . .
C27 C 0.8555(4) 0.9659(4) 0.1199(4) 0.0559(13) Uani 1 1 d . . .
C28 C 0.7712(5) 1.1720(5) -0.1353(4) 0.0778(16) Uani 1 1 d . . .
H28A H 0.7296 1.1614 -0.1864 0.117 Uiso 1 1 calc R . .
H28B H 0.8514 1.1856 -0.1604 0.117 Uiso 1 1 calc R . .
H28C H 0.7240 1.2359 -0.1175 0.117 Uiso 1 1 calc R . .
C29 C 0.7352(4) 0.9829(4) -0.0482(4) 0.0548(12) Uani 1 1 d . . .
C30 C 0.7407(4) 0.8887(4) 0.0464(4) 0.0520(12) Uani 1 1 d . . .
C31 C 0.6797(4) 0.7909(4) 0.0527(3) 0.0537(12) Uani 1 1 d . . .
C32 C 0.7516(5) 0.7305(4) -0.0182(4) 0.0706(16) Uani 1 1 d . . .
H32A H 0.7586 0.7850 -0.0839 0.106 Uiso 1 1 calc R . .
H32B H 0.7090 0.6756 -0.0230 0.106 Uiso 1 1 calc R . .
H32C H 0.8325 0.6928 0.0073 0.106 Uiso 1 1 calc R . .
C33 C 0.5447(4) 0.8351(4) 0.0219(4) 0.0658(14) Uani 1 1 d . . .
H33A H 0.5411 0.8781 -0.0487 0.099 Uiso 1 1 calc R . .
H33B H 0.5027 0.8828 0.0601 0.099 Uiso 1 1 calc R . .
H33C H 0.5057 0.7722 0.0350 0.099 Uiso 1 1 calc R . .
C34 C 0.6840(4) 0.7099(4) 0.1614(3) 0.0535(12) Uani 1 1 d . . .
H34 H 0.7702 0.6811 0.1817 0.064 Uiso 1 1 calc R . .
C35 C 0.6105(5) 0.7612(4) 0.2386(4) 0.0644(14) Uani 1 1 d . . .
H35A H 0.6606 0.7447 0.2962 0.077 Uiso 1 1 calc R . .
H35B H 0.5852 0.8429 0.2086 0.077 Uiso 1 1 calc R . .
C36 C 0.5213(4) 0.6207(4) 0.2373(4) 0.0593(13) Uani 1 1 d . . .
C37 C 0.6248(4) 0.6113(4) 0.1768(3) 0.0565(13) Uani 1 1 d . . .
C38 C 0.6562(5) 0.5202(4) 0.1428(4) 0.0595(13) Uani 1 1 d . . .
H38 H 0.7279 0.5103 0.1039 0.071 Uiso 1 1 calc R . .
C39 C 0.5801(5) 0.4426(4) 0.1668(4) 0.0664(14) Uani 1 1 d . . .
C40 C 0.4743(5) 0.4577(5) 0.2245(4) 0.0754(16) Uani 1 1 d . . .
H40 H 0.4229 0.4064 0.2390 0.090 Uiso 1 1 calc R . .
C41 C 0.4435(5) 0.5470(5) 0.2608(4) 0.0721(15) Uani 1 1 d . . .
H41 H 0.3722 0.5572 0.3001 0.087 Uiso 1 1 calc R . .
C42 C 0.6100(8) 0.3496(6) 0.1277(6) 0.096(2) Uani 1 1 d . . .
F1 F 1.0515(5) 0.4967(9) 0.1070(5) 0.269(5) Uani 1 1 d . . .
F2 F 1.1765(6) 0.3966(5) 0.2068(5) 0.201(3) Uani 1 1 d . . .
F3 F 1.1592(5) 0.5640(5) 0.1649(5) 0.193(3) Uani 1 1 d . . .
F4 F 0.6571(7) 0.3664(4) 0.0419(4) 0.204(3) Uani 1 1 d . . .
F5 F 0.6849(7) 0.2640(5) 0.1842(5) 0.211(3) Uani 1 1 d . . .
F6 F 0.5194(5) 0.3034(5) 0.1276(5) 0.203(3) Uani 1 1 d . . .
C9 C 0.6907(6) 0.1671(5) 0.5241(4) 0.0648(15) Uani 1 1 d . . .
C8 C 0.7157(7) 0.0504(6) 0.5964(4) 0.0808(19) 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
N1 C9 1.282(7) . ?
N1 C5 1.376(6) . ?
N2 C8 1.367(7) . ?
N2 C6 1.371(8) . ?
N2 C7 1.458(8) . ?
N3 C30 1.277(5) . ?
N3 C27 1.377(5) . ?
N4 C29 1.370(6) . ?
N4 C22 1.394(6) . ?
N4 C28 1.451(6) . ?
O1 C8 1.226(7) . ?
O2 C15 1.359(6) . ?
O2 C14 1.444(6) . ?
O3 C29 1.217(5) . ?
O4 C36 1.350(5) . ?
O4 C35 1.458(5) . ?
C1 C2 1.352(12) . ?
C1 C6 1.401(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.376(12) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(8) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C10 C9 1.510(6) . ?
C10 C13 1.522(7) . ?
C10 C11 1.538(7) . ?
C10 C12 1.549(7) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C16 1.505(6) . ?
C13 C14 1.553(7) . ?
C13 H13 0.9800 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C20 1.368(7) . ?
C15 C16 1.369(7) . ?
C16 C17 1.361(6) . ?
C17 C18 1.391(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.352(8) . ?
C18 C21 1.441(9) . ?
C19 C20 1.366(8) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 F1 1.251(10) . ?
C21 F3 1.280(8) . ?
C21 F2 1.299(9) . ?
C22 C27 1.376(7) . ?
C22 C23 1.412(6) . ?
C23 C24 1.380(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.378(8) . ?
C24 H24 0.9300 . ?
C25 C26 1.358(7) . ?
C25 H25 0.9300 . ?
C26 C27 1.371(7) . ?
C26 H26 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C30 1.459(7) . ?
C30 C31 1.535(6) . ?
C31 C32 1.522(6) . ?
C31 C34 1.530(6) . ?
C31 C33 1.530(7) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 C37 1.503(6) . ?
C34 C35 1.530(6) . ?
C34 H34 0.9800 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 C41 1.366(6) . ?
C36 C37 1.370(6) . ?
C37 C38 1.368(6) . ?
C38 C39 1.390(6) . ?
C38 H38 0.9300 . ?
C39 C40 1.376(7) . ?
C39 C42 1.437(8) . ?
C40 C41 1.367(7) . ?
C40 H40 0.9300 . ?
C41 H41 0.9300 . ?
C42 F4 1.237(7) . ?
C42 F5 1.285(8) . ?
C42 F6 1.285(7) . ?
C9 C8 1.477(8) . ?

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 C5 120.0(5) . . ?
C8 N2 C6 121.9(6) . . ?
C8 N2 C7 117.9(7) . . ?
C6 N2 C7 120.2(6) . . ?
C30 N3 C27 119.6(4) . . ?
C29 N4 C22 120.5(4) . . ?
C29 N4 C28 118.4(4) . . ?
C22 N4 C28 121.0(4) . . ?
C15 O2 C14 106.9(4) . . ?
C36 O4 C35 107.1(3) . . ?
C2 C1 C6 119.3(9) . . ?
C2 C1 H1 120.4 . . ?
C6 C1 H1 120.4 . . ?
C1 C2 C3 122.0(7) . . ?
C1 C2 H2 119.0 . . ?
C3 C2 H2 119.0 . . ?
C4 C3 C2 119.5(9) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 119.4(8) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 117.7(6) . . ?
N1 C5 C6 121.4(6) . . ?
C4 C5 C6 120.9(6) . . ?
N2 C6 C5 118.7(5) . . ?
N2 C6 C1 122.4(8) . . ?
C5 C6 C1 118.9(8) . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C10 C13 108.9(5) . . ?
C9 C10 C11 107.5(4) . . ?
C13 C10 C11 109.4(4) . . ?
C9 C10 C12 110.9(4) . . ?
C13 C10 C12 110.0(4) . . ?
C11 C10 C12 110.1(5) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C16 C13 C10 114.9(4) . . ?
C16 C13 C14 99.9(4) . . ?
C10 C13 C14 113.7(4) . . ?
C16 C13 H13 109.3 . . ?
C10 C13 H13 109.3 . . ?
C14 C13 H13 109.3 . . ?
O2 C14 C13 106.8(4) . . ?
O2 C14 H14A 110.4 . . ?
C13 C14 H14A 110.4 . . ?
O2 C14 H14B 110.4 . . ?
C13 C14 H14B 110.4 . . ?
H14A C14 H14B 108.6 . . ?
O2 C15 C20 123.8(5) . . ?
O2 C15 C16 113.3(5) . . ?
C20 C15 C16 122.9(5) . . ?
C17 C16 C15 118.8(5) . . ?
C17 C16 C13 132.1(5) . . ?
C15 C16 C13 109.1(4) . . ?
C16 C17 C18 119.3(5) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C19 C18 C17 120.2(5) . . ?
C19 C18 C21 121.0(6) . . ?
C17 C18 C21 118.8(6) . . ?
C18 C19 C20 121.6(5) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
C19 C20 C15 117.2(6) . . ?
C19 C20 H20 121.4 . . ?
C15 C20 H20 121.4 . . ?
F1 C21 F3 104.9(8) . . ?
F1 C21 F2 101.6(9) . . ?
F3 C21 F2 101.0(7) . . ?
F1 C21 C18 115.9(8) . . ?
F3 C21 C18 116.4(8) . . ?
F2 C21 C18 114.9(7) . . ?
C27 C22 N4 119.3(4) . . ?
C27 C22 C23 119.7(5) . . ?
N4 C22 C23 121.0(5) . . ?
C24 C23 C22 118.2(5) . . ?
C24 C23 H23 120.9 . . ?
C22 C23 H23 120.9 . . ?
C25 C24 C23 121.7(5) . . ?
C25 C24 H24 119.2 . . ?
C23 C24 H24 119.2 . . ?
C26 C25 C24 118.8(6) . . ?
C26 C25 H25 120.6 . . ?
C24 C25 H25 120.6 . . ?
C25 C26 C27 121.8(5) . . ?
C25 C26 H26 119.1 . . ?
C27 C26 H26 119.1 . . ?
C26 C27 C22 119.9(4) . . ?
C26 C27 N3 119.2(5) . . ?
C22 C27 N3 120.9(5) . . ?
N4 C28 H28A 109.5 . . ?
N4 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
N4 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O3 C29 N4 120.3(5) . . ?
O3 C29 C30 124.1(4) . . ?
N4 C29 C30 115.6(4) . . ?
N3 C30 C29 123.6(4) . . ?
N3 C30 C31 117.9(4) . . ?
C29 C30 C31 118.5(4) . . ?
C32 C31 C34 110.8(4) . . ?
C32 C31 C33 109.8(4) . . ?
C34 C31 C33 108.6(4) . . ?
C32 C31 C30 107.6(3) . . ?
C34 C31 C30 109.0(4) . . ?
C33 C31 C30 111.1(4) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C37 C34 C31 113.5(4) . . ?
C37 C34 C35 100.7(3) . . ?
C31 C34 C35 115.0(4) . . ?
C37 C34 H34 109.1 . . ?
C31 C34 H34 109.1 . . ?
C35 C34 H34 109.1 . . ?
O4 C35 C34 107.5(3) . . ?
O4 C35 H35A 110.2 . . ?
C34 C35 H35A 110.2 . . ?
O4 C35 H35B 110.2 . . ?
C34 C35 H35B 110.2 . . ?
H35A C35 H35B 108.5 . . ?
O4 C36 C41 123.3(4) . . ?
O4 C36 C37 113.6(4) . . ?
C41 C36 C37 123.2(5) . . ?
C38 C37 C36 118.7(4) . . ?
C38 C37 C34 132.2(4) . . ?
C36 C37 C34 109.1(4) . . ?
C37 C38 C39 119.5(5) . . ?
C37 C38 H38 120.3 . . ?
C39 C38 H38 120.3 . . ?
C40 C39 C38 119.9(5) . . ?
C40 C39 C42 120.4(5) . . ?
C38 C39 C42 119.6(5) . . ?
C41 C40 C39 121.1(5) . . ?
C41 C40 H40 119.4 . . ?
C39 C40 H40 119.4 . . ?
C36 C41 C40 117.6(5) . . ?
C36 C41 H41 121.2 . . ?
C40 C41 H41 121.2 . . ?
F4 C42 F5 104.8(8) . . ?
F4 C42 F6 104.9(7) . . ?
F5 C42 F6 100.2(6) . . ?
F4 C42 C39 118.1(6) . . ?
F5 C42 C39 111.9(7) . . ?
F6 C42 C39 114.9(7) . . ?
N1 C9 C8 122.2(5) . . ?
N1 C9 C10 118.5(5) . . ?
C8 C9 C10 119.4(6) . . ?
O1 C8 N2 121.7(7) . . ?
O1 C8 C9 122.5(6) . . ?
N2 C8 C9 115.8(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.8(11) . . . . ?
C1 C2 C3 C4 -1.4(11) . . . . ?
C2 C3 C4 C5 2.0(9) . . . . ?
C9 N1 C5 C4 -177.8(5) . . . . ?
C9 N1 C5 C6 3.1(7) . . . . ?
C3 C4 C5 N1 178.8(5) . . . . ?
C3 C4 C5 C6 -2.1(8) . . . . ?
C8 N2 C6 C5 -1.5(8) . . . . ?
C7 N2 C6 C5 178.5(5) . . . . ?
C8 N2 C6 C1 176.5(5) . . . . ?
C7 N2 C6 C1 -3.5(8) . . . . ?
N1 C5 C6 N2 -1.4(7) . . . . ?
C4 C5 C6 N2 179.5(5) . . . . ?
N1 C5 C6 C1 -179.5(5) . . . . ?
C4 C5 C6 C1 1.5(8) . . . . ?
C2 C1 C6 N2 -178.7(6) . . . . ?
C2 C1 C6 C5 -0.8(9) . . . . ?
C9 C10 C13 C16 -179.9(4) . . . . ?
C11 C10 C13 C16 -62.6(5) . . . . ?
C12 C10 C13 C16 58.4(6) . . . . ?
C9 C10 C13 C14 65.8(5) . . . . ?
C11 C10 C13 C14 -176.9(4) . . . . ?
C12 C10 C13 C14 -55.9(6) . . . . ?
C15 O2 C14 C13 19.4(6) . . . . ?
C16 C13 C14 O2 -18.8(6) . . . . ?
C10 C13 C14 O2 104.2(5) . . . . ?
C14 O2 C15 C20 167.6(6) . . . . ?
C14 O2 C15 C16 -11.9(7) . . . . ?
O2 C15 C16 C17 177.8(5) . . . . ?
C20 C15 C16 C17 -1.7(10) . . . . ?
O2 C15 C16 C13 -1.0(7) . . . . ?
C20 C15 C16 C13 179.5(6) . . . . ?
C10 C13 C16 C17 71.4(8) . . . . ?
C14 C13 C16 C17 -166.5(6) . . . . ?
C10 C13 C16 C15 -109.9(5) . . . . ?
C14 C13 C16 C15 12.2(6) . . . . ?
C15 C16 C17 C18 0.7(9) . . . . ?
C13 C16 C17 C18 179.2(6) . . . . ?
C16 C17 C18 C19 0.8(9) . . . . ?
C16 C17 C18 C21 -179.8(7) . . . . ?
C17 C18 C19 C20 -1.5(10) . . . . ?
C21 C18 C19 C20 179.1(7) . . . . ?
C18 C19 C20 C15 0.5(11) . . . . ?
O2 C15 C20 C19 -178.4(6) . . . . ?
C16 C15 C20 C19 1.1(10) . . . . ?
C19 C18 C21 F1 -125.6(10) . . . . ?
C17 C18 C21 F1 55.0(12) . . . . ?
C19 C18 C21 F3 -1.6(13) . . . . ?
C17 C18 C21 F3 179.0(7) . . . . ?
C19 C18 C21 F2 116.2(9) . . . . ?
C17 C18 C21 F2 -63.2(11) . . . . ?
C29 N4 C22 C27 -5.6(6) . . . . ?
C28 N4 C22 C27 177.5(4) . . . . ?
C29 N4 C22 C23 175.8(4) . . . . ?
C28 N4 C22 C23 -1.1(7) . . . . ?
C27 C22 C23 C24 1.5(7) . . . . ?
N4 C22 C23 C24 -180.0(4) . . . . ?
C22 C23 C24 C25 -0.1(8) . . . . ?
C23 C24 C25 C26 -1.4(8) . . . . ?
C24 C25 C26 C27 1.6(8) . . . . ?
C25 C26 C27 C22 -0.2(8) . . . . ?
C25 C26 C27 N3 -179.9(5) . . . . ?
N4 C22 C27 C26 -179.9(4) . . . . ?
C23 C22 C27 C26 -1.3(7) . . . . ?
N4 C22 C27 N3 -0.3(7) . . . . ?
C23 C22 C27 N3 178.3(4) . . . . ?
C30 N3 C27 C26 -178.0(4) . . . . ?
C30 N3 C27 C22 2.3(7) . . . . ?
C22 N4 C29 O3 -173.7(4) . . . . ?
C28 N4 C29 O3 3.3(7) . . . . ?
C22 N4 C29 C30 8.7(6) . . . . ?
C28 N4 C29 C30 -174.3(4) . . . . ?
C27 N3 C30 C29 1.3(7) . . . . ?
C27 N3 C30 C31 178.7(4) . . . . ?
O3 C29 C30 N3 175.7(5) . . . . ?
N4 C29 C30 N3 -6.8(7) . . . . ?
O3 C29 C30 C31 -1.7(7) . . . . ?
N4 C29 C30 C31 175.8(4) . . . . ?
N3 C30 C31 C32 -111.1(5) . . . . ?
C29 C30 C31 C32 66.4(6) . . . . ?
N3 C30 C31 C34 9.0(6) . . . . ?
C29 C30 C31 C34 -173.4(4) . . . . ?
N3 C30 C31 C33 128.6(5) . . . . ?
C29 C30 C31 C33 -53.8(5) . . . . ?
C32 C31 C34 C37 -62.6(5) . . . . ?
C33 C31 C34 C37 58.0(5) . . . . ?
C30 C31 C34 C37 179.2(4) . . . . ?
C32 C31 C34 C35 -177.9(4) . . . . ?
C33 C31 C34 C35 -57.2(5) . . . . ?
C30 C31 C34 C35 63.9(5) . . . . ?
C36 O4 C35 C34 13.3(5) . . . . ?
C37 C34 C35 O4 -13.9(5) . . . . ?
C31 C34 C35 O4 108.5(4) . . . . ?
C35 O4 C36 C41 174.1(5) . . . . ?
C35 O4 C36 C37 -6.9(6) . . . . ?
O4 C36 C37 C38 177.1(5) . . . . ?
C41 C36 C37 C38 -3.9(8) . . . . ?
O4 C36 C37 C34 -2.5(6) . . . . ?
C41 C36 C37 C34 176.4(5) . . . . ?
C31 C34 C37 C38 67.1(7) . . . . ?
C35 C34 C37 C38 -169.5(6) . . . . ?
C31 C34 C37 C36 -113.4(5) . . . . ?
C35 C34 C37 C36 10.1(5) . . . . ?
C36 C37 C38 C39 2.7(8) . . . . ?
C34 C37 C38 C39 -177.8(5) . . . . ?
C37 C38 C39 C40 -0.1(8) . . . . ?
C37 C38 C39 C42 177.3(6) . . . . ?
C38 C39 C40 C41 -1.4(9) . . . . ?
C42 C39 C40 C41 -178.8(6) . . . . ?
O4 C36 C41 C40 -178.7(5) . . . . ?
C37 C36 C41 C40 2.4(9) . . . . ?
C39 C40 C41 C36 0.3(9) . . . . ?
C40 C39 C42 F4 142.0(8) . . . . ?
C38 C39 C42 F4 -35.4(11) . . . . ?
C40 C39 C42 F5 -96.2(9) . . . . ?
C38 C39 C42 F5 86.4(8) . . . . ?
C40 C39 C42 F6 17.3(10) . . . . ?
C38 C39 C42 F6 -160.1(7) . . . . ?
C5 N1 C9 C8 -1.8(7) . . . . ?
C5 N1 C9 C10 178.3(4) . . . . ?
C13 C10 C9 N1 5.1(6) . . . . ?
C11 C10 C9 N1 -113.4(6) . . . . ?
C12 C10 C9 N1 126.2(5) . . . . ?
C13 C10 C9 C8 -174.8(4) . . . . ?
C11 C10 C9 C8 66.7(6) . . . . ?
C12 C10 C9 C8 -53.7(6) . . . . ?
C6 N2 C8 O1 -174.4(6) . . . . ?
C7 N2 C8 O1 5.6(8) . . . . ?
C6 N2 C8 C9 2.6(7) . . . . ?
C7 N2 C8 C9 -177.4(5) . . . . ?
N1 C9 C8 O1 176.0(6) . . . . ?
C10 C9 C8 O1 -4.1(8) . . . . ?
N1 C9 C8 N2 -1.0(7) . . . . ?
C10 C9 C8 N2 178.9(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.065
