# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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 1961424'
loop_
_audit_author_name
_audit_author_address
'Pinhua Li'
;Huaibei Normal University
China
;
_audit_update_record             
;
2019-10-25 deposited with the CCDC.	2020-03-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H13 F3 N2 O2'
_chemical_formula_sum            'C17 H13 F3 N2 O2'
_chemical_formula_weight         334.29

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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.3548(11)
_cell_length_b                   22.501(3)
_cell_length_c                   18.552(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.135(3)
_cell_angle_gamma                90
_cell_volume                     3065.5(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3218
_cell_measurement_theta_min      2.3780
_cell_measurement_theta_max      22.8182

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_F_000             1376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    0.121
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_process_details   SADABS

_exptl_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 APEX II area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16770
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.378
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5998
_reflns_number_gt                3580
_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 SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0550P)²+1.8037P] 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         5998
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1032
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1529
_refine_ls_wR_factor_gt          0.1259
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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 1.0214(5) 0.00453(14) 0.1547(2) 0.0843(11) Uani 1 1 d . . . . .
H1A H 1.1378 -0.0070 0.1383 0.126 Uiso 1 1 calc R U . . .
H1B H 0.9938 -0.0189 0.1959 0.126 Uiso 1 1 calc R U . . .
H1C H 0.9294 -0.0017 0.1167 0.126 Uiso 1 1 calc R U . . .
C2 C 0.8717(4) 0.09040(12) 0.19875(14) 0.0496(7) Uani 1 1 d . . . . .
C3 C 0.7074(4) 0.06157(12) 0.20284(15) 0.0541(7) Uani 1 1 d . . . . .
H3A H 0.6951 0.0223 0.1877 0.065 Uiso 1 1 calc R U . . .
C4 C 0.5610(4) 0.09130(12) 0.22955(14) 0.0500(7) Uani 1 1 d . . . . .
H4A H 0.4500 0.0719 0.2322 0.060 Uiso 1 1 calc R U . . .
C5 C 0.5781(4) 0.14922(11) 0.25222(13) 0.0434(6) Uani 1 1 d . . . . .
C6 C 0.7428(4) 0.17821(11) 0.24683(14) 0.0478(7) Uani 1 1 d . . . . .
H6A H 0.7550 0.2175 0.2617 0.057 Uiso 1 1 calc R U . . .
C7 C 0.8877(4) 0.14930(12) 0.21968(14) 0.0522(7) Uani 1 1 d . . . . .
H7A H 0.9972 0.1693 0.2153 0.063 Uiso 1 1 calc R U . . .
C8 C 0.4253(4) 0.18221(12) 0.28379(15) 0.0531(7) Uani 1 1 d . . . . .
C9 C 0.4780(4) 0.20930(12) 0.35704(14) 0.0461(6) Uani 1 1 d . . . . .
C10 C 0.5143(4) 0.16640(13) 0.41615(15) 0.0548(7) Uani 1 1 d . . . . .
C11 C 0.5975(6) 0.15165(16) 0.54319(18) 0.0880(12) Uani 1 1 d . . . . .
H11A H 0.6324 0.1744 0.5855 0.132 Uiso 1 1 calc R U . . .
H11B H 0.4878 0.1300 0.5512 0.132 Uiso 1 1 calc R U . . .
H11C H 0.6929 0.1242 0.5333 0.132 Uiso 1 1 calc R U . . .
C12 C 0.5903(4) 0.25277(13) 0.48921(14) 0.0494(7) Uani 1 1 d . . . . .
C13 C 0.5554(4) 0.28899(12) 0.42857(14) 0.0462(6) Uani 1 1 d . . . . .
C14 C 0.6493(4) 0.27917(16) 0.55434(16) 0.0634(8) Uani 1 1 d . . . . .
H14A H 0.6723 0.2557 0.5951 0.076 Uiso 1 1 calc R U . . .
C15 C 0.6738(4) 0.33930(17) 0.55881(18) 0.0707(9) Uani 1 1 d . . . . .
H15A H 0.7137 0.3568 0.6022 0.085 Uiso 1 1 calc R U . . .
C16 C 0.6385(5) 0.37356(14) 0.49822(19) 0.0678(9) Uani 1 1 d . . . . .
C17 C 0.5804(4) 0.35039(13) 0.43344(16) 0.0558(7) Uani 1 1 d . . . . .
H17A H 0.5579 0.3747 0.3934 0.067 Uiso 1 1 calc R U . . .
C18 C 0.5002(8) 0.53817(18) 0.0966(3) 0.142(2) Uani 1 1 d . . . . .
H18A H 0.6132 0.5502 0.0774 0.213 Uiso 1 1 calc R U . . .
H18B H 0.4061 0.5381 0.0586 0.213 Uiso 1 1 calc R U . . .
H18C H 0.4688 0.5654 0.1337 0.213 Uiso 1 1 calc R U . . .
C19 C 0.3712(5) 0.45534(14) 0.15613(16) 0.0621(8) Uani 1 1 d . . . . .
C20 C 0.2001(5) 0.48029(13) 0.15618(16) 0.0683(9) Uani 1 1 d . . . . .
H20A H 0.1766 0.5164 0.1331 0.082 Uiso 1 1 calc R U . . .
C21 C 0.0636(5) 0.45139(12) 0.19068(15) 0.0584(8) Uani 1 1 d . . . . .
H21A H -0.0522 0.4681 0.1900 0.070 Uiso 1 1 calc R U . . .
C22 C 0.0962(4) 0.39849(11) 0.22592(13) 0.0451(6) Uani 1 1 d . . . . .
C23 C 0.2691(4) 0.37373(12) 0.22463(15) 0.0513(7) Uani 1 1 d . . . . .
H23A H 0.2935 0.3378 0.2481 0.062 Uiso 1 1 calc R U . . .
C24 C 0.4041(4) 0.40149(13) 0.18928(15) 0.0570(8) Uani 1 1 d . . . . .
H24A H 0.5182 0.3839 0.1877 0.068 Uiso 1 1 calc R U . . .
C25 C -0.0485(4) 0.36650(12) 0.26321(15) 0.0528(7) Uani 1 1 d . . . . .
C26 C 0.0026(3) 0.34687(12) 0.34019(14) 0.0443(6) Uani 1 1 d . . . . .
C27 C 0.0445(4) 0.39552(12) 0.39211(14) 0.0468(7) Uani 1 1 d . . . . .
C28 C 0.1452(5) 0.42263(14) 0.51434(17) 0.0693(9) Uani 1 1 d . . . . .
H28A H 0.1785 0.4041 0.5598 0.104 Uiso 1 1 calc R U . . .
H28B H 0.2462 0.4453 0.4986 0.104 Uiso 1 1 calc R U . . .
H28C H 0.0430 0.4485 0.5199 0.104 Uiso 1 1 calc R U . . .
C29 C 0.0986(3) 0.31701(12) 0.47952(13) 0.0441(6) Uani 1 1 d . . . . .
C30 C 0.0535(4) 0.27499(12) 0.42586(14) 0.0455(6) Uani 1 1 d . . . . .
C31 C 0.1421(4) 0.29807(14) 0.54985(15) 0.0580(8) Uani 1 1 d . . . . .
H31A H 0.1707 0.3257 0.5859 0.070 Uiso 1 1 calc R U . . .
C32 C 0.1427(4) 0.23893(16) 0.56569(18) 0.0698(9) Uani 1 1 d . . . . .
H32A H 0.1721 0.2261 0.6125 0.084 Uiso 1 1 calc R U . . .
C33 C 0.0996(5) 0.19843(14) 0.51222(19) 0.0697(9) Uani 1 1 d . . . . .
C34 C 0.0542(4) 0.21438(13) 0.44239(17) 0.0588(8) Uani 1 1 d . . . . .
H34A H 0.0249 0.1860 0.4072 0.071 Uiso 1 1 calc R U . . .
F1 F 0.3658(3) 0.22669(8) 0.23803(9) 0.0775(6) Uani 1 1 d . . . . .
F2 F 0.2759(2) 0.14662(8) 0.29040(10) 0.0785(6) Uani 1 1 d . . . . .
F3 F 0.6653(3) 0.43315(9) 0.50367(12) 0.0996(7) Uani 1 1 d . . . . .
F4 F -0.1014(3) 0.31731(8) 0.22419(9) 0.0849(6) Uani 1 1 d . . . . .
F5 F -0.2042(2) 0.40027(9) 0.26565(10) 0.0815(6) Uani 1 1 d . . . . .
F6 F 0.1021(4) 0.13959(9) 0.52894(12) 0.1075(8) Uani 1 1 d . . . . .
N1 N 0.4974(3) 0.26578(10) 0.36203(11) 0.0475(5) Uani 1 1 d . . . . .
N2 N 0.5657(3) 0.19191(10) 0.48142(12) 0.0546(6) Uani 1 1 d . . . . .
N3 N 0.0960(3) 0.37677(9) 0.46051(11) 0.0455(5) Uani 1 1 d . . . . .
N4 N 0.0067(3) 0.29128(10) 0.35510(11) 0.0470(5) Uani 1 1 d . . . . .
O1 O 1.0259(3) 0.06560(9) 0.17402(12) 0.0735(6) Uani 1 1 d . . . . .
O2 O 0.5001(4) 0.11280(10) 0.40820(12) 0.0826(7) Uani 1 1 d . . . . .
O3 O 0.5189(4) 0.48058(11) 0.12587(15) 0.0986(9) Uani 1 1 d . . . . .
O4 O 0.0353(3) 0.44812(9) 0.37568(11) 0.0659(6) 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 O1 1.420(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O1 1.365(3) . ?
C2 C3 1.377(4) . ?
C2 C7 1.384(4) . ?
C3 C4 1.382(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.373(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.384(4) . ?
C5 C8 1.493(4) . ?
C6 C7 1.368(4) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9300 . ?
C8 F1 1.368(3) . ?
C8 F2 1.371(3) . ?
C8 C9 1.520(4) . ?
C9 N1 1.282(3) . ?
C9 C10 1.474(4) . ?
C10 O2 1.219(3) . ?
C10 N2 1.374(4) . ?
C11 N2 1.470(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 N2 1.388(3) . ?
C12 C14 1.394(4) . ?
C12 C13 1.402(4) . ?
C13 N1 1.386(3) . ?
C13 C17 1.396(4) . ?
C14 C15 1.367(4) . ?
C14 H14A 0.9300 . ?
C15 C16 1.376(5) . ?
C15 H15A 0.9300 . ?
C16 C17 1.357(4) . ?
C16 F3 1.358(3) . ?
C17 H17A 0.9300 . ?
C18 O3 1.409(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 O3 1.373(4) . ?
C19 C24 1.374(4) . ?
C19 C20 1.378(5) . ?
C20 C21 1.382(4) . ?
C20 H20A 0.9300 . ?
C21 C22 1.373(4) . ?
C21 H21A 0.9300 . ?
C22 C23 1.390(4) . ?
C22 C25 1.487(4) . ?
C23 C24 1.370(4) . ?
C23 H23A 0.9300 . ?
C24 H24A 0.9300 . ?
C25 F4 1.367(3) . ?
C25 F5 1.377(3) . ?
C25 C26 1.522(4) . ?
C26 N4 1.281(3) . ?
C26 C27 1.479(4) . ?
C27 O4 1.223(3) . ?
C27 N3 1.371(3) . ?
C28 N3 1.467(3) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 N3 1.390(3) . ?
C29 C31 1.393(4) . ?
C29 C30 1.400(4) . ?
C30 N4 1.388(3) . ?
C30 C34 1.398(4) . ?
C31 C32 1.363(4) . ?
C31 H31A 0.9300 . ?
C32 C33 1.371(5) . ?
C32 H32A 0.9300 . ?
C33 F6 1.360(3) . ?
C33 C34 1.368(4) . ?
C34 H34A 0.9300 . ?

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
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 125.0(3) . . ?
O1 C2 C7 115.2(3) . . ?
C3 C2 C7 119.8(3) . . ?
C2 C3 C4 119.6(3) . . ?
C2 C3 H3A 120.2 . . ?
C4 C3 H3A 120.2 . . ?
C5 C4 C3 120.6(3) . . ?
C5 C4 H4A 119.7 . . ?
C3 C4 H4A 119.7 . . ?
C4 C5 C6 119.4(3) . . ?
C4 C5 C8 122.3(3) . . ?
C6 C5 C8 118.3(2) . . ?
C7 C6 C5 120.3(2) . . ?
C7 C6 H6A 119.8 . . ?
C5 C6 H6A 119.8 . . ?
C6 C7 C2 120.2(3) . . ?
C6 C7 H7A 119.9 . . ?
C2 C7 H7A 119.9 . . ?
F1 C8 F2 104.6(2) . . ?
F1 C8 C5 110.0(2) . . ?
F2 C8 C5 111.7(2) . . ?
F1 C8 C9 108.6(2) . . ?
F2 C8 C9 108.7(2) . . ?
C5 C8 C9 112.9(2) . . ?
N1 C9 C10 125.5(3) . . ?
N1 C9 C8 119.0(2) . . ?
C10 C9 C8 115.4(2) . . ?
O2 C10 N2 122.5(3) . . ?
O2 C10 C9 123.2(3) . . ?
N2 C10 C9 114.3(2) . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C14 122.9(3) . . ?
N2 C12 C13 118.2(2) . . ?
C14 C12 C13 118.8(3) . . ?
N1 C13 C17 117.6(2) . . ?
N1 C13 C12 122.0(2) . . ?
C17 C13 C12 120.4(3) . . ?
C15 C14 C12 120.5(3) . . ?
C15 C14 H14A 119.7 . . ?
C12 C14 H14A 119.7 . . ?
C14 C15 C16 119.1(3) . . ?
C14 C15 H15A 120.4 . . ?
C16 C15 H15A 120.4 . . ?
C17 C16 F3 118.8(3) . . ?
C17 C16 C15 123.0(3) . . ?
F3 C16 C15 118.2(3) . . ?
C16 C17 C13 118.1(3) . . ?
C16 C17 H17A 120.9 . . ?
C13 C17 H17A 120.9 . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C19 C24 115.1(3) . . ?
O3 C19 C20 125.1(3) . . ?
C24 C19 C20 119.8(3) . . ?
C19 C20 C21 119.7(3) . . ?
C19 C20 H20A 120.2 . . ?
C21 C20 H20A 120.2 . . ?
C22 C21 C20 121.1(3) . . ?
C22 C21 H21A 119.5 . . ?
C20 C21 H21A 119.5 . . ?
C21 C22 C23 118.4(3) . . ?
C21 C22 C25 122.1(3) . . ?
C23 C22 C25 119.5(2) . . ?
C24 C23 C22 120.9(3) . . ?
C24 C23 H23A 119.6 . . ?
C22 C23 H23A 119.6 . . ?
C23 C24 C19 120.1(3) . . ?
C23 C24 H24A 119.9 . . ?
C19 C24 H24A 119.9 . . ?
F4 C25 F5 104.5(2) . . ?
F4 C25 C22 109.6(2) . . ?
F5 C25 C22 111.5(2) . . ?
F4 C25 C26 108.1(2) . . ?
F5 C25 C26 107.0(2) . . ?
C22 C25 C26 115.5(2) . . ?
N4 C26 C27 125.5(2) . . ?
N4 C26 C25 119.2(2) . . ?
C27 C26 C25 115.4(2) . . ?
O4 C27 N3 122.5(2) . . ?
O4 C27 C26 123.2(2) . . ?
N3 C27 C26 114.3(2) . . ?
N3 C28 H28A 109.5 . . ?
N3 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
N3 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N3 C29 C31 122.2(2) . . ?
N3 C29 C30 118.3(2) . . ?
C31 C29 C30 119.5(3) . . ?
N4 C30 C34 117.6(2) . . ?
N4 C30 C29 122.1(2) . . ?
C34 C30 C29 120.4(2) . . ?
C32 C31 C29 119.9(3) . . ?
C32 C31 H31A 120.0 . . ?
C29 C31 H31A 120.0 . . ?
C31 C32 C33 119.7(3) . . ?
C31 C32 H32A 120.2 . . ?
C33 C32 H32A 120.2 . . ?
F6 C33 C34 118.1(3) . . ?
F6 C33 C32 118.8(3) . . ?
C34 C33 C32 123.1(3) . . ?
C33 C34 C30 117.5(3) . . ?
C33 C34 H34A 121.3 . . ?
C30 C34 H34A 121.3 . . ?
C9 N1 C13 117.8(2) . . ?
C10 N2 C12 122.1(2) . . ?
C10 N2 C11 117.0(3) . . ?
C12 N2 C11 120.9(3) . . ?
C27 N3 C29 122.1(2) . . ?
C27 N3 C28 117.3(2) . . ?
C29 N3 C28 120.5(2) . . ?
C26 N4 C30 117.6(2) . . ?
C2 O1 C1 118.2(3) . . ?
C19 O3 C18 118.4(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
O1 C2 C3 C4 179.4(2) . . . . ?
C7 C2 C3 C4 -1.6(4) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C3 C4 C5 C6 1.2(4) . . . . ?
C3 C4 C5 C8 -177.8(2) . . . . ?
C4 C5 C6 C7 -0.5(4) . . . . ?
C8 C5 C6 C7 178.6(2) . . . . ?
C5 C6 C7 C2 -1.3(4) . . . . ?
O1 C2 C7 C6 -178.5(2) . . . . ?
C3 C2 C7 C6 2.4(4) . . . . ?
C4 C5 C8 F1 -112.2(3) . . . . ?
C6 C5 C8 F1 68.7(3) . . . . ?
C4 C5 C8 F2 3.4(3) . . . . ?
C6 C5 C8 F2 -175.6(2) . . . . ?
C4 C5 C8 C9 126.3(3) . . . . ?
C6 C5 C8 C9 -52.8(3) . . . . ?
F1 C8 C9 N1 -14.2(4) . . . . ?
F2 C8 C9 N1 -127.5(3) . . . . ?
C5 C8 C9 N1 108.1(3) . . . . ?
F1 C8 C9 C10 169.7(2) . . . . ?
F2 C8 C9 C10 56.4(3) . . . . ?
C5 C8 C9 C10 -68.1(3) . . . . ?
N1 C9 C10 O2 -177.3(3) . . . . ?
C8 C9 C10 O2 -1.5(4) . . . . ?
N1 C9 C10 N2 2.7(4) . . . . ?
C8 C9 C10 N2 178.6(2) . . . . ?
N2 C12 C13 N1 0.1(4) . . . . ?
C14 C12 C13 N1 179.6(2) . . . . ?
N2 C12 C13 C17 -179.1(3) . . . . ?
C14 C12 C13 C17 0.3(4) . . . . ?
N2 C12 C14 C15 179.1(3) . . . . ?
C13 C12 C14 C15 -0.4(4) . . . . ?
C12 C14 C15 C16 0.3(5) . . . . ?
C14 C15 C16 C17 -0.2(5) . . . . ?
C14 C15 C16 F3 -179.4(3) . . . . ?
F3 C16 C17 C13 179.3(3) . . . . ?
C15 C16 C17 C13 0.1(5) . . . . ?
N1 C13 C17 C16 -179.5(3) . . . . ?
C12 C13 C17 C16 -0.2(4) . . . . ?
O3 C19 C20 C21 -177.8(3) . . . . ?
C24 C19 C20 C21 1.1(5) . . . . ?
C19 C20 C21 C22 1.0(4) . . . . ?
C20 C21 C22 C23 -1.6(4) . . . . ?
C20 C21 C22 C25 -179.8(3) . . . . ?
C21 C22 C23 C24 0.2(4) . . . . ?
C25 C22 C23 C24 178.5(2) . . . . ?
C22 C23 C24 C19 1.8(4) . . . . ?
O3 C19 C24 C23 176.5(3) . . . . ?
C20 C19 C24 C23 -2.4(4) . . . . ?
C21 C22 C25 F4 107.1(3) . . . . ?
C23 C22 C25 F4 -71.1(3) . . . . ?
C21 C22 C25 F5 -8.2(3) . . . . ?
C23 C22 C25 F5 173.6(2) . . . . ?
C21 C22 C25 C26 -130.6(3) . . . . ?
C23 C22 C25 C26 51.2(3) . . . . ?
F4 C25 C26 N4 6.4(4) . . . . ?
F5 C25 C26 N4 118.5(3) . . . . ?
C22 C25 C26 N4 -116.7(3) . . . . ?
F4 C25 C26 C27 -173.7(2) . . . . ?
F5 C25 C26 C27 -61.6(3) . . . . ?
C22 C25 C26 C27 63.2(3) . . . . ?
N4 C26 C27 O4 -178.5(3) . . . . ?
C25 C26 C27 O4 1.6(4) . . . . ?
N4 C26 C27 N3 1.9(4) . . . . ?
C25 C26 C27 N3 -178.0(2) . . . . ?
N3 C29 C30 N4 -0.1(4) . . . . ?
C31 C29 C30 N4 179.1(2) . . . . ?
N3 C29 C30 C34 -180.0(2) . . . . ?
C31 C29 C30 C34 -0.8(4) . . . . ?
N3 C29 C31 C32 180.0(3) . . . . ?
C30 C29 C31 C32 0.8(4) . . . . ?
C29 C31 C32 C33 -0.3(5) . . . . ?
C31 C32 C33 F6 179.6(3) . . . . ?
C31 C32 C33 C34 -0.3(5) . . . . ?
F6 C33 C34 C30 -179.5(3) . . . . ?
C32 C33 C34 C30 0.4(5) . . . . ?
N4 C30 C34 C33 -179.7(3) . . . . ?
C29 C30 C34 C33 0.2(4) . . . . ?
C10 C9 N1 C13 -0.7(4) . . . . ?
C8 C9 N1 C13 -176.4(2) . . . . ?
C17 C13 N1 C9 178.5(3) . . . . ?
C12 C13 N1 C9 -0.8(4) . . . . ?
O2 C10 N2 C12 176.8(3) . . . . ?
C9 C10 N2 C12 -3.3(4) . . . . ?
O2 C10 N2 C11 -2.1(5) . . . . ?
C9 C10 N2 C11 177.8(3) . . . . ?
C14 C12 N2 C10 -177.4(3) . . . . ?
C13 C12 N2 C10 2.1(4) . . . . ?
C14 C12 N2 C11 1.4(4) . . . . ?
C13 C12 N2 C11 -179.1(3) . . . . ?
O4 C27 N3 C29 177.2(3) . . . . ?
C26 C27 N3 C29 -3.2(4) . . . . ?
O4 C27 N3 C28 -1.4(4) . . . . ?
C26 C27 N3 C28 178.1(2) . . . . ?
C31 C29 N3 C27 -176.7(3) . . . . ?
C30 C29 N3 C27 2.5(4) . . . . ?
C31 C29 N3 C28 1.9(4) . . . . ?
C30 C29 N3 C28 -178.9(3) . . . . ?
C27 C26 N4 C30 0.3(4) . . . . ?
C25 C26 N4 C30 -179.9(2) . . . . ?
C34 C30 N4 C26 178.7(3) . . . . ?
C29 C30 N4 C26 -1.3(4) . . . . ?
C3 C2 O1 C1 -3.7(4) . . . . ?
C7 C2 O1 C1 177.2(3) . . . . ?
C24 C19 O3 C18 -174.4(3) . . . . ?
C20 C19 O3 C18 4.5(5) . . . . ?

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
C24 H24A F5 0.93 2.46 3.140(3) 129.6 1_655
C20 H20A O2 0.93 2.62 3.506(4) 159.1 2
C15 H15A O1 0.93 2.63 3.254(4) 124.7 4_566
C7 H7A F2 0.93 2.47 3.077(3) 123.2 1_655
C3 H3A O4 0.93 2.61 3.397(3) 142.5 2_545
C1 H1A O4 0.96 2.63 3.572(4) 166.0 2_645
C24 H24A F5 0.93 2.46 3.140(3) 129.6 1_655
C20 H20A O2 0.93 2.62 3.506(4) 159.1 2
C15 H15A O1 0.93 2.63 3.254(4) 124.7 4_566
C7 H7A F2 0.93 2.47 3.077(3) 123.2 1_655
C3 H3A O4 0.93 2.61 3.397(3) 142.5 2_545
C1 H1A O4 0.96 2.63 3.572(4) 166.0 2_645
C24 H24A F5 0.93 2.46 3.140(3) 129.6 1_655
C20 H20A O2 0.93 2.62 3.506(4) 159.1 2
C15 H15A O1 0.93 2.63 3.254(4) 124.7 4_566
C7 H7A F2 0.93 2.47 3.077(3) 123.2 1_655
C3 H3A O4 0.93 2.61 3.397(3) 142.5 2_545
C1 H1A O4 0.96 2.63 3.572(4) 166.0 2_645
C1 H1A O4 0.96 2.63 3.572(4) 166.0 2_645
C3 H3A O4 0.93 2.61 3.397(3) 142.5 2_545
C7 H7A F2 0.93 2.47 3.077(3) 123.2 1_655
C15 H15A O1 0.93 2.63 3.254(4) 124.7 4_566
C20 H20A O2 0.93 2.62 3.506(4) 159.1 2
C24 H24A F5 0.93 2.46 3.140(3) 129.6 1_655

_refine_diff_density_max         0.317
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.042

_shelxl_version_number           2014-3

