# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# 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_d-14
_database_code_depnum_ccdc_archive 'CCDC 2170109'
loop_
_audit_author_name
_audit_author_address
dd
;ergg
China
;
_audit_update_record             
;
2022-05-03 deposited with the CCDC.	2022-09-19 downloaded from the CCDC.
;
_audit_creation_date             2022-01-27
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H21 F N4 O6'
_chemical_formula_sum            'C26 H21 F N4 O6'
_chemical_formula_weight         504.47
_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                   12.3686(8)
_cell_length_b                   8.7434(7)
_cell_length_c                   21.3869(12)
_cell_angle_alpha                90
_cell_angle_beta                 90.743(6)
_cell_angle_gamma                90
_cell_volume                     2312.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3600
_cell_measurement_temperature    199.99(10)
_cell_measurement_theta_max      27.9520
_cell_measurement_theta_min      2.9920
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51158
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10333
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.502
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      199.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -31.00  69.00   1.00    3.00    --  -11.35  19.00   0.00  100
  2  ω    -42.00  63.00   1.00    3.00    --  -11.35  77.00-120.00  105
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0564561000
_diffrn_orient_matrix_UB_12      -0.0130238000
_diffrn_orient_matrix_UB_13      0.0021668000
_diffrn_orient_matrix_UB_21      0.0058446000
_diffrn_orient_matrix_UB_22      -0.0700701000
_diffrn_orient_matrix_UB_23      -0.0162468000
_diffrn_orient_matrix_UB_31      0.0084825000
_diffrn_orient_matrix_UB_32      -0.0386651000
_diffrn_orient_matrix_UB_33      0.0288310000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3224
_reflns_number_total             4067
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         4067
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0426
_refine_ls_restrained_S_all      1.040
_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)+(0.0429P)²+0.4714P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.0994
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C14(H14), C15(H15), C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C)
;
_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 0.39773(10) 0.60806(14) 0.45385(5) 0.0516(3) Uani 1 1 d . . . . .
O1 O 0.26569(9) 0.10461(14) 0.56365(5) 0.0306(3) Uani 1 1 d . . . . .
O2 O 0.07597(12) 0.5561(2) 0.61664(7) 0.0557(4) Uani 1 1 d . . . . .
O3 O 0.14207(11) 0.06025(17) 0.69126(6) 0.0451(4) Uani 1 1 d . . . . .
O4 O 0.48918(9) 0.42685(15) 0.72916(6) 0.0356(3) Uani 1 1 d . . . . .
O5 O 0.49288(11) 0.07818(17) 0.60119(6) 0.0457(4) Uani 1 1 d . . . . .
O6 O 0.66182(11) 0.06174(18) 0.62813(7) 0.0511(4) Uani 1 1 d . . . . .
N1 N 0.32647(11) 0.33196(16) 0.52359(6) 0.0249(3) Uani 1 1 d . . . . .
N2 N 0.18625(11) 0.38678(18) 0.71984(6) 0.0311(4) Uani 1 1 d . . . . .
N3 N 0.57211(12) 0.12042(18) 0.63148(7) 0.0306(4) Uani 1 1 d . . . . .
N4 N 0.60355(12) 0.4456(2) 0.73297(7) 0.0403(4) Uani 1 1 d . . . . .
C1 C 0.34211(12) 0.4812(2) 0.54608(7) 0.0227(4) Uani 1 1 d . . . . .
C2 C 0.31834(12) 0.4890(2) 0.60987(7) 0.0223(4) Uani 1 1 d . . . . .
C3 C 0.32740(14) 0.6254(2) 0.64174(8) 0.0317(4) Uani 1 1 d . . . . .
H3 H 0.311990 0.629817 0.684151 0.038 Uiso 1 1 calc R U . . .
C4 C 0.35956(15) 0.7556(2) 0.61034(9) 0.0372(5) Uani 1 1 d . . . . .
H4 H 0.365214 0.848043 0.631667 0.045 Uiso 1 1 calc R U . . .
C5 C 0.38329(15) 0.7491(2) 0.54756(9) 0.0355(5) Uani 1 1 d . . . . .
H5 H 0.404798 0.836923 0.526565 0.043 Uiso 1 1 calc R U . . .
C6 C 0.37504(14) 0.6127(2) 0.51622(8) 0.0308(4) Uani 1 1 d . . . . .
C7 C 0.28383(13) 0.33190(19) 0.63042(7) 0.0214(4) Uani 1 1 d . . . . .
C8 C 0.29135(13) 0.2380(2) 0.57013(7) 0.0222(4) Uani 1 1 d . . . . .
C9 C 0.16643(13) 0.3263(2) 0.65749(7) 0.0271(4) Uani 1 1 d . . . . .
C10 C 0.11826(14) 0.1629(2) 0.65574(8) 0.0315(4) Uani 1 1 d . . . . .
C11 C 0.03121(14) 0.1607(3) 0.60779(8) 0.0358(5) Uani 1 1 d . . . . .
C12 C 0.01368(14) 0.3071(3) 0.58511(8) 0.0387(5) Uani 1 1 d . . . . .
C13 C 0.08381(15) 0.4189(3) 0.61820(8) 0.0361(5) Uani 1 1 d . . . . .
C14 C -0.06332(16) 0.3333(3) 0.53830(9) 0.0561(7) Uani 1 1 d . . . . .
H14 H -0.075629 0.431108 0.522694 0.067 Uiso 1 1 calc R U . . .
C15 C -0.12055(17) 0.2097(4) 0.51590(11) 0.0681(9) Uani 1 1 d . . . . .
H15 H -0.171136 0.224240 0.483900 0.082 Uiso 1 1 calc R U . . .
C16 C -0.10480(17) 0.0651(4) 0.53970(11) 0.0646(8) Uani 1 1 d . . . . .
H16 H -0.146592 -0.015370 0.524363 0.078 Uiso 1 1 calc R U . . .
C17 C -0.02843(16) 0.0367(3) 0.58577(9) 0.0487(6) Uani 1 1 d . . . . .
H17 H -0.017285 -0.061256 0.601480 0.058 Uiso 1 1 calc R U . . .
C18 C 0.34842(13) 0.2627(2) 0.68704(7) 0.0235(4) Uani 1 1 d . . . . .
H18 H 0.345469 0.151124 0.683211 0.028 Uiso 1 1 calc R U . . .
C19 C 0.28182(14) 0.3081(2) 0.74489(7) 0.0317(4) Uani 1 1 d . . . . .
H19A H 0.261073 0.218064 0.768368 0.038 Uiso 1 1 calc R U . . .
H19B H 0.323279 0.375345 0.772150 0.038 Uiso 1 1 calc R U . . .
C20 C 0.09442(16) 0.3878(3) 0.76189(9) 0.0504(6) Uani 1 1 d . . . . .
H20A H 0.035676 0.443382 0.742869 0.076 Uiso 1 1 calc R U . . .
H20B H 0.115054 0.436177 0.800537 0.076 Uiso 1 1 calc R U . . .
H20C H 0.072061 0.284632 0.769941 0.076 Uiso 1 1 calc R U . . .
C21 C 0.46485(13) 0.3076(2) 0.69252(7) 0.0239(4) Uani 1 1 d . . . . .
C22 C 0.55960(13) 0.2479(2) 0.67240(7) 0.0230(4) Uani 1 1 d . . . . .
C23 C 0.64465(14) 0.3365(2) 0.69920(8) 0.0288(4) Uani 1 1 d . . . . .
C24 C 0.76396(15) 0.3201(3) 0.69463(9) 0.0425(5) Uani 1 1 d . . . . .
H24A H 0.798612 0.405408 0.714830 0.064 Uiso 1 1 calc R U . . .
H24B H 0.783911 0.317439 0.651416 0.064 Uiso 1 1 calc R U . . .
H24C H 0.786376 0.226948 0.714699 0.064 Uiso 1 1 calc R U . . .
C25 C 0.33243(16) 0.2801(2) 0.45866(8) 0.0361(5) Uani 1 1 d . . . . .
H25A H 0.341107 0.169814 0.458004 0.043 Uiso 1 1 calc R U . . .
H25B H 0.395441 0.325054 0.439355 0.043 Uiso 1 1 calc R U . . .
C26 C 0.2325(2) 0.3230(3) 0.42111(9) 0.0574(7) Uani 1 1 d . . . . .
H26A H 0.237559 0.281303 0.379723 0.086 Uiso 1 1 calc R U . . .
H26B H 0.227005 0.432343 0.418668 0.086 Uiso 1 1 calc R U . . .
H26C H 0.169646 0.282554 0.441104 0.086 Uiso 1 1 calc R U . . .


_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 C6 1.3673(19) . ?
O1 C8 1.216(2) . ?
O2 C13 1.204(3) . ?
O3 C10 1.210(2) . ?
O4 N4 1.4254(18) . ?
O4 C21 1.336(2) . ?
O5 N3 1.2248(18) . ?
O6 N3 1.2254(19) . ?
N1 C1 1.403(2) . ?
N1 C8 1.366(2) . ?
N1 C25 1.464(2) . ?
N2 C9 1.452(2) . ?
N2 C19 1.463(2) . ?
N2 C20 1.458(2) . ?
N3 C22 1.427(2) . ?
N4 C23 1.304(2) . ?
C1 C2 1.401(2) . ?
C1 C6 1.379(2) . ?
C2 C3 1.377(2) . ?
C2 C7 1.506(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.379(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.372(3) . ?
C7 C8 1.533(2) . ?
C7 C9 1.571(2) . ?
C7 C18 1.564(2) . ?
C9 C10 1.548(3) . ?
C9 C13 1.544(3) . ?
C10 C11 1.477(2) . ?
C11 C12 1.385(3) . ?
C11 C17 1.390(3) . ?
C12 C13 1.481(3) . ?
C12 C14 1.392(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.374(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.377(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.378(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9800 . ?
C18 C19 1.547(2) . ?
C18 C21 1.496(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.358(2) . ?
C22 C23 1.421(2) . ?
C23 C24 1.487(3) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C26 1.512(3) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

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
C21 O4 N4 109.83(13) . . ?
C1 N1 C25 127.23(14) . . ?
C8 N1 C1 110.69(13) . . ?
C8 N1 C25 121.69(15) . . ?
C9 N2 C19 106.90(14) . . ?
C9 N2 C20 116.42(15) . . ?
C20 N2 C19 114.16(14) . . ?
O5 N3 O6 124.18(16) . . ?
O5 N3 C22 117.88(15) . . ?
O6 N3 C22 117.93(15) . . ?
C23 N4 O4 106.13(14) . . ?
C2 C1 N1 110.45(14) . . ?
C6 C1 N1 131.04(15) . . ?
C6 C1 C2 118.51(16) . . ?
C1 C2 C7 107.67(14) . . ?
C3 C2 C1 120.51(16) . . ?
C3 C2 C7 131.81(15) . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.63(16) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.32(18) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.75(18) . . ?
C6 C5 H5 120.1 . . ?
F1 C6 C1 119.53(17) . . ?
F1 C6 C5 119.18(16) . . ?
C5 C6 C1 121.27(16) . . ?
C2 C7 C8 102.87(12) . . ?
C2 C7 C9 113.77(14) . . ?
C2 C7 C18 115.78(13) . . ?
C8 C7 C9 111.09(13) . . ?
C8 C7 C18 114.10(14) . . ?
C18 C7 C9 99.67(12) . . ?
O1 C8 N1 125.36(15) . . ?
O1 C8 C7 126.23(15) . . ?
N1 C8 C7 108.32(14) . . ?
N2 C9 C7 100.43(12) . . ?
N2 C9 C10 114.75(14) . . ?
N2 C9 C13 114.28(16) . . ?
C10 C9 C7 112.16(14) . . ?
C13 C9 C7 113.03(13) . . ?
C13 C9 C10 102.67(14) . . ?
O3 C10 C9 125.37(15) . . ?
O3 C10 C11 126.55(18) . . ?
C11 C10 C9 107.79(16) . . ?
C12 C11 C10 109.90(17) . . ?
C12 C11 C17 121.47(18) . . ?
C17 C11 C10 128.6(2) . . ?
C11 C12 C13 110.79(16) . . ?
C11 C12 C14 120.4(2) . . ?
C14 C12 C13 128.8(2) . . ?
O2 C13 C9 126.18(19) . . ?
O2 C13 C12 126.74(19) . . ?
C12 C13 C9 107.03(18) . . ?
C12 C14 H14 121.1 . . ?
C15 C14 C12 117.8(3) . . ?
C15 C14 H14 121.1 . . ?
C14 C15 H15 119.2 . . ?
C14 C15 C16 121.6(2) . . ?
C16 C15 H15 119.2 . . ?
C15 C16 H16 119.3 . . ?
C15 C16 C17 121.4(2) . . ?
C17 C16 H16 119.3 . . ?
C11 C17 H17 121.4 . . ?
C16 C17 C11 117.3(2) . . ?
C16 C17 H17 121.4 . . ?
C7 C18 H18 107.6 . . ?
C19 C18 C7 104.37(13) . . ?
C19 C18 H18 107.6 . . ?
C21 C18 C7 116.18(13) . . ?
C21 C18 H18 107.6 . . ?
C21 C18 C19 113.10(13) . . ?
N2 C19 C18 105.29(13) . . ?
N2 C19 H19A 110.7 . . ?
N2 C19 H19B 110.7 . . ?
C18 C19 H19A 110.7 . . ?
C18 C19 H19B 110.7 . . ?
H19A C19 H19B 108.8 . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O4 C21 C18 117.37(14) . . ?
O4 C21 C22 107.28(14) . . ?
C22 C21 C18 135.11(16) . . ?
C21 C22 N3 126.55(15) . . ?
C21 C22 C23 107.46(15) . . ?
C23 C22 N3 125.99(15) . . ?
N4 C23 C22 109.30(15) . . ?
N4 C23 C24 120.08(16) . . ?
C22 C23 C24 130.62(17) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N1 C25 H25A 109.2 . . ?
N1 C25 H25B 109.2 . . ?
N1 C25 C26 112.09(16) . . ?
H25A C25 H25B 107.9 . . ?
C26 C25 H25A 109.2 . . ?
C26 C25 H25B 109.2 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

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
O3 C10 C11 C12 167.90(18) . . . . ?
O3 C10 C11 C17 -12.1(3) . . . . ?
O4 N4 C23 C22 1.0(2) . . . . ?
O4 N4 C23 C24 -178.20(16) . . . . ?
O4 C21 C22 N3 -179.04(15) . . . . ?
O4 C21 C22 C23 0.50(18) . . . . ?
O5 N3 C22 C21 15.9(2) . . . . ?
O5 N3 C22 C23 -163.55(16) . . . . ?
O6 N3 C22 C21 -165.24(17) . . . . ?
O6 N3 C22 C23 15.3(3) . . . . ?
N1 C1 C2 C3 -179.57(15) . . . . ?
N1 C1 C2 C7 -0.31(18) . . . . ?
N1 C1 C6 F1 0.3(3) . . . . ?
N1 C1 C6 C5 178.92(17) . . . . ?
N2 C9 C10 O3 -37.7(2) . . . . ?
N2 C9 C10 C11 136.47(15) . . . . ?
N2 C9 C13 O2 39.5(3) . . . . ?
N2 C9 C13 C12 -138.18(15) . . . . ?
N3 C22 C23 N4 178.58(16) . . . . ?
N3 C22 C23 C24 -2.4(3) . . . . ?
N4 O4 C21 C18 175.30(14) . . . . ?
N4 O4 C21 C22 0.08(18) . . . . ?
C1 N1 C8 O1 175.94(15) . . . . ?
C1 N1 C8 C7 -0.85(18) . . . . ?
C1 N1 C25 C26 -76.8(2) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C1 C2 C7 C8 -0.18(16) . . . . ?
C1 C2 C7 C9 -120.44(14) . . . . ?
C1 C2 C7 C18 124.95(15) . . . . ?
C2 C1 C6 F1 -179.41(15) . . . . ?
C2 C1 C6 C5 -0.8(3) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C2 C7 C8 O1 -176.13(16) . . . . ?
C2 C7 C8 N1 0.62(16) . . . . ?
C2 C7 C9 N2 -78.30(16) . . . . ?
C2 C7 C9 C10 159.37(13) . . . . ?
C2 C7 C9 C13 43.9(2) . . . . ?
C2 C7 C18 C19 93.13(16) . . . . ?
C2 C7 C18 C21 -32.1(2) . . . . ?
C3 C2 C7 C8 178.96(18) . . . . ?
C3 C2 C7 C9 58.7(2) . . . . ?
C3 C2 C7 C18 -55.9(2) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 F1 179.34(16) . . . . ?
C4 C5 C6 C1 0.8(3) . . . . ?
C6 C1 C2 C3 0.2(2) . . . . ?
C6 C1 C2 C7 179.49(14) . . . . ?
C7 C2 C3 C4 -178.62(16) . . . . ?
C7 C9 C10 O3 76.0(2) . . . . ?
C7 C9 C10 C11 -109.75(15) . . . . ?
C7 C9 C13 O2 -74.6(2) . . . . ?
C7 C9 C13 C12 107.76(16) . . . . ?
C7 C18 C19 N2 3.16(18) . . . . ?
C7 C18 C21 O4 94.20(17) . . . . ?
C7 C18 C21 C22 -92.3(2) . . . . ?
C8 N1 C1 C2 0.75(19) . . . . ?
C8 N1 C1 C6 -179.02(17) . . . . ?
C8 N1 C25 C26 95.3(2) . . . . ?
C8 C7 C9 N2 166.19(14) . . . . ?
C8 C7 C9 C10 43.87(18) . . . . ?
C8 C7 C9 C13 -71.63(19) . . . . ?
C8 C7 C18 C19 -147.73(14) . . . . ?
C8 C7 C18 C21 87.01(18) . . . . ?
C9 N2 C19 C18 27.45(18) . . . . ?
C9 C7 C8 O1 -54.0(2) . . . . ?
C9 C7 C8 N1 122.71(15) . . . . ?
C9 C7 C18 C19 -29.30(16) . . . . ?
C9 C7 C18 C21 -154.56(14) . . . . ?
C9 C10 C11 C12 -6.23(19) . . . . ?
C9 C10 C11 C17 173.77(17) . . . . ?
C10 C9 C13 O2 164.40(19) . . . . ?
C10 C9 C13 C12 -13.28(17) . . . . ?
C10 C11 C12 C13 -2.7(2) . . . . ?
C10 C11 C12 C14 178.61(16) . . . . ?
C10 C11 C17 C16 -179.05(18) . . . . ?
C11 C12 C13 O2 -167.19(19) . . . . ?
C11 C12 C13 C9 10.5(2) . . . . ?
C11 C12 C14 C15 0.1(3) . . . . ?
C12 C11 C17 C16 0.9(3) . . . . ?
C12 C14 C15 C16 1.6(3) . . . . ?
C13 C9 C10 O3 -162.33(18) . . . . ?
C13 C9 C10 C11 11.89(17) . . . . ?
C13 C12 C14 C15 -178.34(19) . . . . ?
C14 C12 C13 O2 11.4(3) . . . . ?
C14 C12 C13 C9 -170.93(17) . . . . ?
C14 C15 C16 C17 -2.1(3) . . . . ?
C15 C16 C17 C11 0.7(3) . . . . ?
C17 C11 C12 C13 177.33(16) . . . . ?
C17 C11 C12 C14 -1.4(3) . . . . ?
C18 C7 C8 O1 57.6(2) . . . . ?
C18 C7 C8 N1 -125.60(14) . . . . ?
C18 C7 C9 N2 45.55(16) . . . . ?
C18 C7 C9 C10 -76.77(15) . . . . ?
C18 C7 C9 C13 167.73(15) . . . . ?
C18 C21 C22 N3 7.0(3) . . . . ?
C18 C21 C22 C23 -173.48(17) . . . . ?
C19 N2 C9 C7 -46.38(16) . . . . ?
C19 N2 C9 C10 74.10(17) . . . . ?
C19 N2 C9 C13 -167.68(15) . . . . ?
C19 C18 C21 O4 -26.5(2) . . . . ?
C19 C18 C21 C22 147.04(19) . . . . ?
C20 N2 C9 C7 -175.33(16) . . . . ?
C20 N2 C9 C10 -54.8(2) . . . . ?
C20 N2 C9 C13 63.4(2) . . . . ?
C20 N2 C19 C18 157.69(17) . . . . ?
C21 O4 N4 C23 -0.68(19) . . . . ?
C21 C18 C19 N2 130.35(15) . . . . ?
C21 C22 C23 N4 -1.0(2) . . . . ?
C21 C22 C23 C24 178.10(18) . . . . ?
C25 N1 C1 C2 173.62(15) . . . . ?
C25 N1 C1 C6 -6.1(3) . . . . ?
C25 N1 C8 O1 2.6(3) . . . . ?
C25 N1 C8 C7 -174.18(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.771
_oxdiff_exptl_absorpt_empirical_full_min 0.460
####################################################################### 
# 
# 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_d-15
_database_code_depnum_ccdc_archive 'CCDC 2170112'
loop_
_audit_author_name
_audit_author_address
dd
;ergg
China
;
_audit_update_record             
;
2022-05-03 deposited with the CCDC.	2022-09-19 downloaded from the CCDC.
;
_audit_creation_date             2022-01-27
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H19 F N4 O6'
_chemical_formula_sum            'C25 H19 F N4 O6'
_chemical_formula_weight         490.44
_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      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                   12.6086(7)
_cell_length_b                   8.8642(5)
_cell_length_c                   20.3547(14)
_cell_angle_alpha                90
_cell_angle_beta                 92.860(5)
_cell_angle_gamma                90
_cell_volume                     2272.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3969
_cell_measurement_temperature    199.92(16)
_cell_measurement_theta_max      28.9840
_cell_measurement_theta_min      2.8070
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74417
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9504
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.004
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      199.92(16)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      8.00  35.00   1.00    2.00    --   12.05 -37.00  60.00   27
  2  ω     -4.00  21.00   1.00    2.00    --  -11.51 -99.00  30.00   25
  3  ω    -12.00  87.00   1.00    2.00    --   12.05  37.00-120.00   99
  4  ω    -53.00  -9.00   1.00    2.00    --   12.05 -37.00  60.00   44
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0106234000
_diffrn_orient_matrix_UB_12      0.0773980000
_diffrn_orient_matrix_UB_13      -0.0055571000
_diffrn_orient_matrix_UB_21      0.0199015000
_diffrn_orient_matrix_UB_22      -0.0181365000
_diffrn_orient_matrix_UB_23      -0.0310044000
_diffrn_orient_matrix_UB_31      -0.0516289000
_diffrn_orient_matrix_UB_32      0.0088812000
_diffrn_orient_matrix_UB_33      -0.0150135000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3227
_reflns_number_total             3994
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         3994
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0490
_refine_ls_restrained_S_all      1.062
_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)+(0.0617P)²+0.8723P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1309
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C12(H12), C13(H13), C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
;
_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 0.59872(12) 0.40056(15) 0.54602(6) 0.0560(4) Uani 1 1 d . . . . .
O1 O 0.35201(13) 0.93057(19) 0.38050(9) 0.0548(5) Uani 1 1 d . . . . .
O2 O 0.52178(13) 0.91957(18) 0.40165(8) 0.0500(4) Uani 1 1 d . . . . .
O3 O 0.75094(12) 0.88347(16) 0.43557(7) 0.0401(4) Uani 1 1 d . . . . .
O4 O 0.92088(15) 0.4259(2) 0.36210(11) 0.0699(6) Uani 1 1 d . . . . .
O5 O 0.86409(14) 0.92807(19) 0.30236(9) 0.0560(5) Uani 1 1 d . . . . .
O6 O 0.50800(11) 0.57754(16) 0.26628(7) 0.0363(4) Uani 1 1 d . . . . .
N1 N 0.68350(13) 0.66407(18) 0.47576(8) 0.0317(4) Uani 1 1 d . . . . .
N2 N 0.80185(14) 0.6164(2) 0.26526(9) 0.0386(4) Uani 1 1 d . . . . .
N3 N 0.43956(14) 0.87616(19) 0.37299(9) 0.0345(4) Uani 1 1 d . . . . .
N4 N 0.39606(13) 0.5570(2) 0.26623(9) 0.0405(5) Uani 1 1 d . . . . .
C1 C 0.68489(15) 0.5099(2) 0.38514(9) 0.0282(4) Uani 1 1 d . . . . .
C2 C 0.67275(18) 0.3758(2) 0.35131(11) 0.0384(5) Uani 1 1 d . . . . .
H2 H 0.688481 0.369747 0.307229 0.046 Uiso 1 1 calc R U . . .
C3 C 0.63664(19) 0.2498(2) 0.38408(12) 0.0446(6) Uani 1 1 d . . . . .
H3 H 0.629356 0.158389 0.361856 0.054 Uiso 1 1 calc R U . . .
C4 C 0.61161(18) 0.2583(2) 0.44875(12) 0.0418(6) Uani 1 1 d . . . . .
H4 H 0.586764 0.173551 0.470101 0.050 Uiso 1 1 calc R U . . .
C5 C 0.62347(16) 0.3931(2) 0.48186(10) 0.0354(5) Uani 1 1 d . . . . .
C6 C 0.66153(14) 0.5191(2) 0.45117(9) 0.0279(4) Uani 1 1 d . . . . .
C7 C 0.72116(15) 0.7542(2) 0.42796(10) 0.0294(5) Uani 1 1 d . . . . .
C8 C 0.72169(15) 0.6636(2) 0.36384(9) 0.0276(4) Uani 1 1 d . . . . .
C9 C 0.83160(16) 0.6644(2) 0.33133(11) 0.0356(5) Uani 1 1 d . . . . .
C10 C 0.88474(17) 0.8218(3) 0.33758(11) 0.0417(6) Uani 1 1 d . . . . .
C11 C 0.97174(17) 0.8087(3) 0.38967(11) 0.0475(6) Uani 1 1 d . . . . .
C12 C 1.03030(19) 0.9235(4) 0.41974(13) 0.0614(8) Uani 1 1 d . . . . .
H12 H 1.019905 1.024094 0.408197 0.074 Uiso 1 1 calc R U . . .
C13 C 1.1071(2) 0.8790(5) 0.46920(14) 0.0717(10) Uani 1 1 d . . . . .
H13 H 1.148352 0.951983 0.491156 0.086 Uiso 1 1 calc R U . . .
C14 C 1.1216(2) 0.7292(5) 0.48516(17) 0.0809(10) Uani 1 1 d . . . . .
H14 H 1.171259 0.703773 0.518621 0.097 Uiso 1 1 calc R U . . .
C15 C 1.0662(2) 0.6186(4) 0.45403(14) 0.0677(8) Uani 1 1 d . . . . .
H15 H 1.079703 0.517856 0.464104 0.081 Uiso 1 1 calc R U . . .
C16 C 0.98834(17) 0.6584(3) 0.40635(12) 0.0503(6) Uani 1 1 d . . . . .
C17 C 0.91588(18) 0.5606(3) 0.36713(12) 0.0478(6) Uani 1 1 d . . . . .
C18 C 0.65083(15) 0.7388(2) 0.30703(9) 0.0280(4) Uani 1 1 d . . . . .
H18 H 0.654689 0.848380 0.313212 0.034 Uiso 1 1 calc R U . . .
C19 C 0.70703(16) 0.7007(3) 0.24354(10) 0.0366(5) Uani 1 1 d . . . . .
H19A H 0.661444 0.639945 0.214262 0.044 Uiso 1 1 calc R U . . .
H19B H 0.726104 0.792021 0.220701 0.044 Uiso 1 1 calc R U . . .
C20 C 0.8848(2) 0.6170(3) 0.21807(13) 0.0595(7) Uani 1 1 d . . . . .
H20A H 0.908595 0.718495 0.211644 0.089 Uiso 1 1 calc R U . . .
H20B H 0.857122 0.576566 0.176927 0.089 Uiso 1 1 calc R U . . .
H20C H 0.943254 0.556153 0.234481 0.089 Uiso 1 1 calc R U . . .
C21 C 0.53667(15) 0.6954(2) 0.30425(9) 0.0274(4) Uani 1 1 d . . . . .
C22 C 0.44667(15) 0.7517(2) 0.32867(9) 0.0281(4) Uani 1 1 d . . . . .
C23 C 0.36016(16) 0.6631(2) 0.30322(10) 0.0332(5) Uani 1 1 d . . . . .
C24 C 0.24418(18) 0.6758(3) 0.31245(13) 0.0515(6) Uani 1 1 d . . . . .
H24A H 0.218950 0.771433 0.296026 0.077 Uiso 1 1 calc R U . . .
H24B H 0.231259 0.667978 0.358406 0.077 Uiso 1 1 calc R U . . .
H24C H 0.207507 0.596022 0.288869 0.077 Uiso 1 1 calc R U . . .
C25 C 0.6778(2) 0.7143(3) 0.54370(11) 0.0490(6) Uani 1 1 d . . . . .
H25A H 0.610788 0.684819 0.560134 0.073 Uiso 1 1 calc R U . . .
H25B H 0.684333 0.822166 0.545556 0.073 Uiso 1 1 calc R U . . .
H25C H 0.734382 0.669115 0.570135 0.073 Uiso 1 1 calc R U . . .


_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 C5 1.359(2) . ?
O1 N3 1.221(2) . ?
O2 N3 1.226(2) . ?
O3 C7 1.213(2) . ?
O4 C17 1.201(3) . ?
O5 C10 1.205(3) . ?
O6 N4 1.423(2) . ?
O6 C21 1.338(2) . ?
N1 C6 1.402(2) . ?
N1 C7 1.362(3) . ?
N1 C25 1.458(3) . ?
N2 C9 1.442(3) . ?
N2 C19 1.459(3) . ?
N2 C20 1.454(3) . ?
N3 C22 1.431(3) . ?
N4 C23 1.300(3) . ?
C1 C2 1.379(3) . ?
C1 C6 1.393(3) . ?
C1 C8 1.509(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.390(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.371(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.376(3) . ?
C5 C6 1.378(3) . ?
C7 C8 1.533(3) . ?
C8 C9 1.565(3) . ?
C8 C18 1.574(3) . ?
C9 C10 1.550(3) . ?
C9 C17 1.559(3) . ?
C10 C11 1.492(3) . ?
C11 C12 1.382(4) . ?
C11 C16 1.388(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.418(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.377(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.344(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.392(4) . ?
C16 C17 1.467(4) . ?
C18 H18 0.9800 . ?
C18 C19 1.542(3) . ?
C18 C21 1.488(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.357(3) . ?
C22 C23 1.421(3) . ?
C23 C24 1.488(3) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

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
C21 O6 N4 109.84(14) . . ?
C6 N1 C25 126.90(17) . . ?
C7 N1 C6 110.63(16) . . ?
C7 N1 C25 122.25(17) . . ?
C9 N2 C19 107.60(16) . . ?
C9 N2 C20 116.92(19) . . ?
C20 N2 C19 113.77(19) . . ?
O1 N3 O2 124.38(18) . . ?
O1 N3 C22 117.97(18) . . ?
O2 N3 C22 117.64(17) . . ?
C23 N4 O6 106.33(15) . . ?
C2 C1 C6 120.57(18) . . ?
C2 C1 C8 131.52(18) . . ?
C6 C1 C8 107.92(16) . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 119.0(2) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.9(2) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.57(19) . . ?
C5 C4 H4 120.2 . . ?
F1 C5 C4 119.23(19) . . ?
F1 C5 C6 119.86(19) . . ?
C4 C5 C6 120.9(2) . . ?
C1 C6 N1 110.50(16) . . ?
C5 C6 N1 130.43(18) . . ?
C5 C6 C1 119.06(18) . . ?
O3 C7 N1 125.40(19) . . ?
O3 C7 C8 126.10(18) . . ?
N1 C7 C8 108.49(16) . . ?
C1 C8 C7 102.35(15) . . ?
C1 C8 C9 114.66(16) . . ?
C1 C8 C18 114.98(15) . . ?
C7 C8 C9 113.51(16) . . ?
C7 C8 C18 112.14(15) . . ?
C9 C8 C18 99.74(15) . . ?
N2 C9 C8 101.44(16) . . ?
N2 C9 C10 115.69(18) . . ?
N2 C9 C17 113.65(19) . . ?
C10 C9 C8 110.98(17) . . ?
C10 C9 C17 102.18(18) . . ?
C17 C9 C8 113.37(17) . . ?
O5 C10 C9 125.1(2) . . ?
O5 C10 C11 127.8(2) . . ?
C11 C10 C9 106.7(2) . . ?
C12 C11 C10 128.0(3) . . ?
C12 C11 C16 121.8(3) . . ?
C16 C11 C10 110.2(2) . . ?
C11 C12 H12 121.9 . . ?
C11 C12 C13 116.2(3) . . ?
C13 C12 H12 121.9 . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.9(3) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 118.9 . . ?
C15 C14 C13 122.2(3) . . ?
C15 C14 H14 118.9 . . ?
C14 C15 H15 120.8 . . ?
C14 C15 C16 118.4(3) . . ?
C16 C15 H15 120.8 . . ?
C11 C16 C15 120.4(3) . . ?
C11 C16 C17 110.6(2) . . ?
C15 C16 C17 128.9(3) . . ?
O4 C17 C9 125.8(2) . . ?
O4 C17 C16 126.9(2) . . ?
C16 C17 C9 107.3(2) . . ?
C8 C18 H18 107.6 . . ?
C19 C18 C8 104.77(15) . . ?
C19 C18 H18 107.6 . . ?
C21 C18 C8 115.50(15) . . ?
C21 C18 H18 107.6 . . ?
C21 C18 C19 113.28(16) . . ?
N2 C19 C18 105.20(16) . . ?
N2 C19 H19A 110.7 . . ?
N2 C19 H19B 110.7 . . ?
C18 C19 H19A 110.7 . . ?
C18 C19 H19B 110.7 . . ?
H19A C19 H19B 108.8 . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O6 C21 C18 117.18(16) . . ?
O6 C21 C22 106.99(16) . . ?
C22 C21 C18 135.70(17) . . ?
C21 C22 N3 126.51(17) . . ?
C21 C22 C23 107.68(17) . . ?
C23 C22 N3 125.80(18) . . ?
N4 C23 C22 109.14(18) . . ?
N4 C23 C24 120.04(19) . . ?
C22 C23 C24 130.8(2) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N1 C25 H25A 109.5 . . ?
N1 C25 H25B 109.5 . . ?
N1 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

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
F1 C5 C6 N1 1.7(3) . . . . ?
F1 C5 C6 C1 -179.00(17) . . . . ?
O1 N3 C22 C21 166.44(19) . . . . ?
O1 N3 C22 C23 -14.8(3) . . . . ?
O2 N3 C22 C21 -14.6(3) . . . . ?
O2 N3 C22 C23 164.18(19) . . . . ?
O3 C7 C8 C1 175.70(19) . . . . ?
O3 C7 C8 C9 51.6(3) . . . . ?
O3 C7 C8 C18 -60.5(2) . . . . ?
O5 C10 C11 C12 17.2(4) . . . . ?
O5 C10 C11 C16 -163.3(2) . . . . ?
O6 N4 C23 C22 -1.0(2) . . . . ?
O6 N4 C23 C24 178.67(19) . . . . ?
O6 C21 C22 N3 178.43(18) . . . . ?
O6 C21 C22 C23 -0.5(2) . . . . ?
N1 C7 C8 C1 -3.1(2) . . . . ?
N1 C7 C8 C9 -127.20(18) . . . . ?
N1 C7 C8 C18 120.69(17) . . . . ?
N2 C9 C10 O5 33.9(3) . . . . ?
N2 C9 C10 C11 -140.18(19) . . . . ?
N2 C9 C17 O4 -36.7(3) . . . . ?
N2 C9 C17 C16 141.96(19) . . . . ?
N3 C22 C23 N4 -177.96(19) . . . . ?
N3 C22 C23 C24 2.4(4) . . . . ?
N4 O6 C21 C18 -176.62(16) . . . . ?
N4 O6 C21 C22 -0.1(2) . . . . ?
C1 C2 C3 C4 1.1(3) . . . . ?
C1 C8 C9 N2 80.26(19) . . . . ?
C1 C8 C9 C10 -156.28(17) . . . . ?
C1 C8 C9 C17 -42.0(2) . . . . ?
C1 C8 C18 C19 -96.27(19) . . . . ?
C1 C8 C18 C21 29.1(2) . . . . ?
C2 C1 C6 N1 177.80(18) . . . . ?
C2 C1 C6 C5 -1.6(3) . . . . ?
C2 C1 C8 C7 -176.9(2) . . . . ?
C2 C1 C8 C9 -53.5(3) . . . . ?
C2 C1 C8 C18 61.3(3) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C3 C4 C5 F1 -179.85(19) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C4 C5 C6 N1 -177.3(2) . . . . ?
C4 C5 C6 C1 2.0(3) . . . . ?
C6 N1 C7 O3 -176.81(18) . . . . ?
C6 N1 C7 C8 2.0(2) . . . . ?
C6 C1 C2 C3 0.1(3) . . . . ?
C6 C1 C8 C7 3.09(19) . . . . ?
C6 C1 C8 C9 126.46(17) . . . . ?
C6 C1 C8 C18 -118.75(17) . . . . ?
C7 N1 C6 C1 0.1(2) . . . . ?
C7 N1 C6 C5 179.5(2) . . . . ?
C7 C8 C9 N2 -162.57(16) . . . . ?
C7 C8 C9 C10 -39.1(2) . . . . ?
C7 C8 C9 C17 75.2(2) . . . . ?
C7 C8 C18 C19 147.35(16) . . . . ?
C7 C8 C18 C21 -87.3(2) . . . . ?
C8 C1 C2 C3 -180.0(2) . . . . ?
C8 C1 C6 N1 -2.2(2) . . . . ?
C8 C1 C6 C5 178.41(17) . . . . ?
C8 C9 C10 O5 -81.0(3) . . . . ?
C8 C9 C10 C11 104.98(19) . . . . ?
C8 C9 C17 O4 78.4(3) . . . . ?
C8 C9 C17 C16 -102.9(2) . . . . ?
C8 C18 C19 N2 -1.7(2) . . . . ?
C8 C18 C21 O6 -91.7(2) . . . . ?
C8 C18 C21 C22 93.0(3) . . . . ?
C9 N2 C19 C18 -27.4(2) . . . . ?
C9 C8 C18 C19 26.90(18) . . . . ?
C9 C8 C18 C21 152.25(16) . . . . ?
C9 C10 C11 C12 -169.0(2) . . . . ?
C9 C10 C11 C16 10.5(3) . . . . ?
C10 C9 C17 O4 -162.1(2) . . . . ?
C10 C9 C17 C16 16.6(2) . . . . ?
C10 C11 C12 C13 178.6(2) . . . . ?
C10 C11 C16 C15 179.8(2) . . . . ?
C10 C11 C16 C17 0.5(3) . . . . ?
C11 C12 C13 C14 0.4(4) . . . . ?
C11 C16 C17 O4 167.4(2) . . . . ?
C11 C16 C17 C9 -11.3(3) . . . . ?
C12 C11 C16 C15 -0.7(4) . . . . ?
C12 C11 C16 C17 -180.0(2) . . . . ?
C12 C13 C14 C15 1.7(5) . . . . ?
C13 C14 C15 C16 -3.2(4) . . . . ?
C14 C15 C16 C11 2.7(4) . . . . ?
C14 C15 C16 C17 -178.1(3) . . . . ?
C15 C16 C17 O4 -11.9(4) . . . . ?
C15 C16 C17 C9 169.5(2) . . . . ?
C16 C11 C12 C13 -0.9(3) . . . . ?
C17 C9 C10 O5 157.9(2) . . . . ?
C17 C9 C10 C11 -16.2(2) . . . . ?
C18 C8 C9 N2 -43.12(18) . . . . ?
C18 C8 C9 C10 80.33(19) . . . . ?
C18 C8 C9 C17 -165.35(18) . . . . ?
C18 C21 C22 N3 -6.0(4) . . . . ?
C18 C21 C22 C23 175.1(2) . . . . ?
C19 N2 C9 C8 45.2(2) . . . . ?
C19 N2 C9 C10 -75.0(2) . . . . ?
C19 N2 C9 C17 167.22(17) . . . . ?
C19 C18 C21 O6 29.1(2) . . . . ?
C19 C18 C21 C22 -146.1(2) . . . . ?
C20 N2 C9 C8 174.63(19) . . . . ?
C20 N2 C9 C10 54.5(3) . . . . ?
C20 N2 C9 C17 -63.3(3) . . . . ?
C20 N2 C19 C18 -158.63(19) . . . . ?
C21 O6 N4 C23 0.7(2) . . . . ?
C21 C18 C19 N2 -128.47(18) . . . . ?
C21 C22 C23 N4 1.0(2) . . . . ?
C21 C22 C23 C24 -178.6(2) . . . . ?
C25 N1 C6 C1 -174.60(19) . . . . ?
C25 N1 C6 C5 4.8(3) . . . . ?
C25 N1 C7 O3 -1.8(3) . . . . ?
C25 N1 C7 C8 176.96(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.297
_oxdiff_exptl_absorpt_empirical_full_min 0.668
