# 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. 
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data_190925_bk_4_94a_0m
_database_code_depnum_ccdc_archive 'CCDC 1998157'
loop_
_audit_author_name
_audit_author_address
'Rong Sheng'
;Zhejiang University
China
;
_audit_update_record             
;
2020-04-21 deposited with the CCDC.	2020-06-25 downloaded from the CCDC.
;
_audit_creation_date             2019-09-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H21 F5 N2 O'
_chemical_formula_sum            'C25 H21 F5 N2 O'
_chemical_formula_weight         460.44
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6898(10)
_cell_length_b                   11.1725(11)
_cell_length_c                   12.0639(13)
_cell_angle_alpha                76.082(4)
_cell_angle_beta                 73.273(4)
_cell_angle_gamma                77.314(4)
_cell_volume                     1074.4(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5161
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.25
_cell_measurement_theta_min      2.48
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1344 before and 0.0833 after correction.
The Ratio of minimum to maximum transmission is 0.7650.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_unetI/netI     0.0635
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11994
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.421
_diffrn_reflns_theta_min         2.356
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.984
_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                3386
_reflns_number_total             4333
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.564
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4333
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0663
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0849P)²+1.1044P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1787
_refine_ls_wR_factor_ref         0.1915
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C11(H11A,H11B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
;
_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
F1 F 0.3348(3) 0.9892(2) 0.2950(4) 0.1270(16) Uani 1 1 d . . . . .
F2 F 0.1244(3) 0.92760(19) 0.40312(19) 0.0712(8) Uani 1 1 d . . . . .
F3 F 0.1590(4) 0.9576(2) 0.2217(2) 0.1039(12) Uani 1 1 d . . . . .
F4 F 1.1588(2) 0.33307(17) 0.53092(15) 0.0424(5) Uani 1 1 d . . . . .
F5 F 1.1771(2) 0.18497(15) 0.43662(17) 0.0413(5) Uani 1 1 d . . . . .
O1 O 0.78940(19) 0.43015(16) 0.29223(16) 0.0249(4) Uani 1 1 d . . . . .
N1 N 0.7397(2) 0.23592(19) 0.34148(19) 0.0247(5) Uani 1 1 d . . . . .
N2 N 0.5212(2) 0.40002(19) 0.32877(18) 0.0222(4) Uani 1 1 d . . . . .
C1 C 0.6725(3) 0.3581(2) 0.3224(2) 0.0202(5) Uani 1 1 d . . . . .
C2 C 0.9157(3) 0.2203(2) 0.3004(2) 0.0265(5) Uani 1 1 d . . . . .
H2A H 0.953520 0.196820 0.221704 0.032 Uiso 1 1 calc R . . . .
H2B H 0.968689 0.156623 0.356459 0.032 Uiso 1 1 calc R . . . .
C3 C 0.9482(3) 0.3522(2) 0.2951(2) 0.0217(5) Uani 1 1 d . . . . .
C4 C 0.4636(3) 0.5292(2) 0.3196(2) 0.0208(5) Uani 1 1 d . . . . .
C5 C 0.5122(3) 0.6084(2) 0.3722(2) 0.0254(5) Uani 1 1 d . . . . .
H5 H 0.595414 0.576709 0.413217 0.031 Uiso 1 1 calc R . . . .
C6 C 0.4409(3) 0.7318(3) 0.3651(2) 0.0281(6) Uani 1 1 d . . . . .
H6 H 0.476107 0.784500 0.400762 0.034 Uiso 1 1 calc R . . . .
C7 C 0.3178(3) 0.7806(2) 0.3065(2) 0.0288(6) Uani 1 1 d . . . . .
C8 C 0.2685(3) 0.7029(3) 0.2536(2) 0.0291(6) Uani 1 1 d . . . . .
H8 H 0.185084 0.735087 0.212808 0.035 Uiso 1 1 calc R . . . .
C9 C 0.3402(3) 0.5791(2) 0.2601(2) 0.0266(5) Uani 1 1 d . . . . .
H9 H 0.305344 0.526892 0.223638 0.032 Uiso 1 1 calc R . . . .
C10 C 0.2368(4) 0.9121(3) 0.3047(3) 0.0364(7) Uani 1 1 d . . . . .
C11 C 0.6501(3) 0.1328(2) 0.3652(2) 0.0279(6) Uani 1 1 d . . . . .
H11A H 0.532067 0.164519 0.388679 0.034 Uiso 1 1 calc R . . . .
H11B H 0.679271 0.069828 0.432299 0.034 Uiso 1 1 calc R . . . .
C12 C 0.6840(3) 0.0703(2) 0.2608(2) 0.0273(6) Uani 1 1 d . . . . .
C13 C 0.6431(4) 0.1364(3) 0.1573(3) 0.0391(7) Uani 1 1 d . . . . .
H13 H 0.595392 0.222022 0.151988 0.047 Uiso 1 1 calc R . . . .
C14 C 0.6706(5) 0.0798(4) 0.0624(3) 0.0550(9) Uani 1 1 d . . . . .
H14 H 0.642841 0.126274 -0.008162 0.066 Uiso 1 1 calc R . . . .
C15 C 0.7384(6) -0.0440(4) 0.0700(3) 0.0668(12) Uani 1 1 d . . . . .
H15 H 0.756828 -0.083405 0.004776 0.080 Uiso 1 1 calc R . . . .
C16 C 0.7795(6) -0.1110(4) 0.1712(4) 0.0664(12) Uani 1 1 d . . . . .
H16 H 0.826199 -0.196798 0.176028 0.080 Uiso 1 1 calc R . . . .
C17 C 0.7531(4) -0.0536(3) 0.2675(3) 0.0433(8) Uani 1 1 d . . . . .
H17 H 0.782725 -0.100043 0.337357 0.052 Uiso 1 1 calc R . . . .
C18 C 0.9819(3) 0.3678(2) 0.4087(2) 0.0241(5) Uani 1 1 d . . . . .
H18A H 0.963677 0.458198 0.409800 0.029 Uiso 1 1 calc R . . . .
H18B H 0.901395 0.329424 0.476845 0.029 Uiso 1 1 calc R . . . .
C19 C 1.1502(3) 0.3119(2) 0.4254(2) 0.0269(5) Uani 1 1 d . . . . .
H19 H 1.235021 0.349770 0.358816 0.032 Uiso 1 1 calc R . . . .
C20 C 1.0687(3) 0.4033(2) 0.1846(2) 0.0218(5) Uani 1 1 d . . . . .
C21 C 1.2077(3) 0.3263(3) 0.1344(2) 0.0292(6) Uani 1 1 d . . . . .
H21 H 1.227343 0.240205 0.168600 0.035 Uiso 1 1 calc R . . . .
C22 C 1.3178(3) 0.3761(3) 0.0336(2) 0.0361(7) Uani 1 1 d . . . . .
H22 H 1.412223 0.323452 -0.001001 0.043 Uiso 1 1 calc R . . . .
C23 C 1.2909(3) 0.5015(3) -0.0164(2) 0.0346(6) Uani 1 1 d . . . . .
H23 H 1.367048 0.534762 -0.084704 0.042 Uiso 1 1 calc R . . . .
C24 C 1.1537(3) 0.5780(3) 0.0329(2) 0.0322(6) Uani 1 1 d . . . . .
H24 H 1.134781 0.664096 -0.001604 0.039 Uiso 1 1 calc R . . . .
C25 C 1.0428(3) 0.5292(2) 0.1334(2) 0.0260(5) Uani 1 1 d . . . . .
H25 H 0.948506 0.582438 0.167302 0.031 Uiso 1 1 calc R . . . .


_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 C10 1.303(4) . ?
F2 C10 1.324(3) . ?
F3 C10 1.308(4) . ?
F4 C19 1.375(3) . ?
F5 C19 1.365(3) . ?
O1 C1 1.349(3) . ?
O1 C3 1.466(3) . ?
N1 C1 1.354(3) . ?
N1 C2 1.450(3) . ?
N1 C11 1.457(3) . ?
N2 C1 1.281(3) . ?
N2 C4 1.408(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.544(3) . ?
C3 C18 1.537(3) . ?
C3 C20 1.514(3) . ?
C4 C5 1.398(4) . ?
C4 C9 1.401(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.375(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.391(4) . ?
C7 C8 1.390(4) . ?
C7 C10 1.481(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.380(4) . ?
C9 H9 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.510(4) . ?
C12 C13 1.387(4) . ?
C12 C17 1.376(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.376(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.371(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.368(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.397(5) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.509(3) . ?
C19 H19 1.0000 . ?
C20 C21 1.393(3) . ?
C20 C25 1.391(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.393(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.382(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.377(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.391(4) . ?
C25 H25 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C3 110.31(18) . . ?
C1 N1 C2 111.1(2) . . ?
C1 N1 C11 124.2(2) . . ?
C2 N1 C11 122.2(2) . . ?
C1 N2 C4 120.0(2) . . ?
O1 C1 N1 109.86(19) . . ?
N2 C1 O1 124.6(2) . . ?
N2 C1 N1 125.6(2) . . ?
N1 C2 H2A 111.5 . . ?
N1 C2 H2B 111.5 . . ?
N1 C2 C3 101.57(19) . . ?
H2A C2 H2B 109.3 . . ?
C3 C2 H2A 111.5 . . ?
C3 C2 H2B 111.5 . . ?
O1 C3 C2 102.77(18) . . ?
O1 C3 C18 104.36(18) . . ?
O1 C3 C20 106.73(18) . . ?
C18 C3 C2 113.5(2) . . ?
C20 C3 C2 115.0(2) . . ?
C20 C3 C18 113.0(2) . . ?
C5 C4 N2 124.8(2) . . ?
C5 C4 C9 118.1(2) . . ?
C9 C4 N2 116.9(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.7(2) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C7 121.0(2) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 C10 120.2(3) . . ?
C8 C7 C6 119.0(2) . . ?
C8 C7 C10 120.8(2) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.3(2) . . ?
C9 C8 H8 119.9 . . ?
C4 C9 H9 119.5 . . ?
C8 C9 C4 121.0(2) . . ?
C8 C9 H9 119.5 . . ?
F1 C10 F2 103.7(3) . . ?
F1 C10 F3 107.0(3) . . ?
F1 C10 C7 114.0(3) . . ?
F2 C10 C7 112.8(2) . . ?
F3 C10 F2 104.1(3) . . ?
F3 C10 C7 114.3(3) . . ?
N1 C11 H11A 108.9 . . ?
N1 C11 H11B 108.9 . . ?
N1 C11 C12 113.2(2) . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C13 C12 C11 120.5(2) . . ?
C17 C12 C11 120.5(2) . . ?
C17 C12 C13 119.0(3) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.0(3) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.7(3) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.3(3) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.2(3) . . ?
C17 C16 H16 119.9 . . ?
C12 C17 C16 119.8(3) . . ?
C12 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C3 C18 H18A 108.3 . . ?
C3 C18 H18B 108.3 . . ?
H18A C18 H18B 107.4 . . ?
C19 C18 C3 115.7(2) . . ?
C19 C18 H18A 108.3 . . ?
C19 C18 H18B 108.3 . . ?
F4 C19 C18 108.1(2) . . ?
F4 C19 H19 110.7 . . ?
F5 C19 F4 105.3(2) . . ?
F5 C19 C18 111.3(2) . . ?
F5 C19 H19 110.7 . . ?
C18 C19 H19 110.7 . . ?
C21 C20 C3 120.9(2) . . ?
C25 C20 C3 120.0(2) . . ?
C25 C20 C21 119.2(2) . . ?
C20 C21 H21 120.1 . . ?
C20 C21 C22 119.7(3) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 H22 119.7 . . ?
C23 C22 C21 120.6(3) . . ?
C23 C22 H22 119.7 . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 120.0(3) . . ?
C24 C23 H23 120.0 . . ?
C23 C24 H24 120.0 . . ?
C23 C24 C25 119.9(3) . . ?
C25 C24 H24 120.0 . . ?
C20 C25 H25 119.7 . . ?
C24 C25 C20 120.7(2) . . ?
C24 C25 H25 119.7 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
