# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_fz01
_database_code_depnum_ccdc_archive 'CCDC 2133310'
loop_
_audit_author_name
_audit_author_address
'fang zheng'
;Fuzhou University
China
;
_audit_update_record             
;
2022-01-11 deposited with the CCDC.	2022-04-06 downloaded from the CCDC.
;
_audit_creation_date             2022-01-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C34 H25 F3 N2 O5, C H Cl3'
_chemical_formula_sum            'C35 H26 Cl3 F3 N2 O5'
_chemical_formula_weight         717.93
_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'
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'
Cl Cl 0.1484 0.1585 '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                   23.784(3)
_cell_length_b                   18.643(2)
_cell_length_c                   7.3210(9)
_cell_angle_alpha                90
_cell_angle_beta                 90.762(3)
_cell_angle_gamma                90
_cell_volume                     3245.9(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3056
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.128
_cell_measurement_theta_min      2.570
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.346
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6807
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1516 before and 0.0652 after correction.
The Ratio of minimum to maximum transmission is 0.9134.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.0
_exptl_crystal_size_mid          0.0
_exptl_crystal_size_min          0.0
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1314
_diffrn_reflns_av_unetI/netI     0.1246
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            37502
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.071
_diffrn_reflns_theta_max         25.071
_diffrn_reflns_theta_min         2.031
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2473
_reflns_number_total             5732
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.905
_refine_diff_density_min         -0.739
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.00105(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         5732
_refine_ls_number_restraints     152
_refine_ls_R_factor_all          0.2177
_refine_ls_R_factor_gt           0.0888
_refine_ls_restrained_S_all      1.211
_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)+(0.0020P)²+7.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1412
_refine_ls_wR_factor_ref         0.1706
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C35-Cl2
 1.73 with sigma of 0.02
 C35-Cl1
 1.73 with sigma of 0.02
 C35-Cl3
 1.73 with sigma of 0.02
 C35A-Cl1A
 1.73 with sigma of 0.02
 C35A-Cl2A
 1.73 with sigma of 0.02
 C35A-Cl3A
 1.73 with sigma of 0.02
 Cl3-Cl1
 2.6 with sigma of 0.02
 Cl1-Cl3
 2.8 with sigma of 0.02
2. Rigid bond restraints
 Cl3A, C35A, Cl2A, Cl1A, Cl1, Cl3, C35, Cl2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
Cl3A \\sim C35A \\sim Cl2A \\sim Cl1A \\sim Cl1 \\sim Cl3 \\sim C35 \\sim Cl2:
within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
Uanis(Cl3A) \\sim Ueq, Uanis(C35A) \\sim Ueq, Uanis(Cl2A) \\sim Ueq,
Uanis(Cl1A) \\sim Ueq, Uanis(Cl1) \\sim Ueq, Uanis(Cl3) \\sim Ueq, Uanis(C35)
\\sim Ueq, Uanis(Cl2) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(C35) \\sim Ueq, Uanis(Cl1) \\sim Ueq, Uanis(Cl3) \\sim Ueq, Uanis(Cl2)
\\sim Ueq, Uanis(Cl2A) \\sim Ueq, Uanis(Cl3A) \\sim Ueq, Uanis(C35A) \\sim Ueq,
Uanis(Cl1A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: Cl3A(0.5) Cl2A(0.5) Cl1A(0.5) Cl1(0.5) C35A(0.5) H35A(0.5)
 Cl3(0.5) Cl2(0.5) C35(0.5) H35(0.5)
5.a Ternary CH refined with riding coordinates:
 C35A(H35A), C35(H35)
5.b Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C21(H21), C28(H28), C19(H19), C22(H22), C24(H24), C18(H18), C27(H27),
 C14(H14), C12(H12), C11(H11), C26(H26), C5(H5), C25(H25), C2(H2), C1(H1A),
 C4(H4), C9(H9), C3(H3), C8(H8)
5.d Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C)
;
_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
F3 F 0.34472(14) 0.3339(2) 0.8313(6) 0.0857(12) Uani 1 1 d . . . . .
O2 O 0.37235(15) 0.5469(2) 1.1438(5) 0.0624(12) Uani 1 1 d . . . . .
F1 F 0.33817(15) 0.3458(2) 1.1233(6) 0.0935(14) Uani 1 1 d . . . . .
O1 O 0.19422(16) 0.6259(2) 0.8420(5) 0.0623(12) Uani 1 1 d . . . . .
O4 O 0.14590(16) 0.3470(3) 0.8036(6) 0.0743(14) Uani 1 1 d . . . . .
O3 O 0.15599(16) 0.4675(3) 0.8105(6) 0.0717(14) Uani 1 1 d . . . . .
F2 F 0.32837(15) 0.2419(2) 0.9987(7) 0.1043(15) Uani 1 1 d . . . . .
O5 O 0.22412(17) 0.2715(3) 0.9930(7) 0.0780(14) Uani 1 1 d . . . . .
N2 N 0.27069(19) 0.4438(3) 0.9265(6) 0.0520(13) Uani 1 1 d . . . . .
N1 N 0.25841(18) 0.5120(3) 0.8927(6) 0.0534(14) Uani 1 1 d . . . . .
H1 H 0.2258 0.5244 0.8512 0.064 Uiso 1 1 calc R . . . .
C20 C 0.4574(2) 0.4166(3) 0.6120(7) 0.0362(13) Uani 1 1 d . . . . .
C21 C 0.4715(2) 0.4203(3) 0.7955(7) 0.0410(14) Uani 1 1 d . . . . .
H21 H 0.5034 0.3965 0.8379 0.049 Uiso 1 1 calc R . . . .
C28 C 0.5498(2) 0.3721(3) 0.5017(8) 0.0419(14) Uani 1 1 d . . . . .
H28 H 0.5674 0.3950 0.5998 0.050 Uiso 1 1 calc R . . . .
C23 C 0.4913(2) 0.3755(3) 0.4807(7) 0.0378(13) Uani 1 1 d . . . . .
C17 C 0.3913(2) 0.4937(3) 0.8563(8) 0.0418(14) Uani 1 1 d . . . . .
C19 C 0.4090(2) 0.4524(3) 0.5524(7) 0.0412(14) Uani 1 1 d . . . . .
H19 H 0.3984 0.4503 0.4298 0.049 Uiso 1 1 calc R . . . .
C22 C 0.4396(2) 0.4581(3) 0.9164(8) 0.0458(15) Uani 1 1 d . . . . .
H22 H 0.4502 0.4600 1.0390 0.055 Uiso 1 1 calc R . . . .
C24 C 0.4668(2) 0.3394(3) 0.3338(8) 0.0460(15) Uani 1 1 d . . . . .
H24 H 0.4279 0.3404 0.3173 0.055 Uiso 1 1 calc R . . . .
C18 C 0.3768(2) 0.4907(3) 0.6730(8) 0.0465(15) Uani 1 1 d . . . . .
H18 H 0.3449 0.5149 0.6308 0.056 Uiso 1 1 calc R . . . .
C15 C 0.3002(2) 0.5626(4) 0.9268(7) 0.0492(16) Uani 1 1 d . . . . .
C16 C 0.3572(2) 0.5337(3) 0.9878(8) 0.0510(16) Uani 1 1 d . . . . .
C10 C 0.2291(2) 0.7448(4) 0.8715(7) 0.0538(17) Uani 1 1 d . . . . .
C7 C 0.2090(2) 0.8938(4) 0.8577(7) 0.0501(16) Uani 1 1 d . . . . .
C27 C 0.5815(2) 0.3347(3) 0.3765(8) 0.0520(16) Uani 1 1 d . . . . .
H27 H 0.6204 0.3333 0.3912 0.062 Uiso 1 1 calc R . . . .
C31 C 0.2325(2) 0.3944(4) 0.9031(8) 0.0537(17) Uani 1 1 d . . . . .
C6 C 0.1984(2) 0.9722(4) 0.8460(7) 0.0521(16) Uani 1 1 d . . . . .
C14 C 0.2904(2) 0.6336(4) 0.9135(7) 0.0528(16) Uani 1 1 d . . . . .
H14 H 0.3207 0.6644 0.9323 0.063 Uiso 1 1 calc R . . . .
C13 C 0.2357(3) 0.6655(4) 0.8716(8) 0.0568(17) Uani 1 1 d . . . . .
C32 C 0.1743(3) 0.4075(5) 0.8364(8) 0.063(2) Uani 1 1 d . . . . .
C12 C 0.2634(3) 0.8661(4) 0.8556(8) 0.0609(18) Uani 1 1 d . . . . .
H12 H 0.2939 0.8972 0.8492 0.073 Uiso 1 1 calc R . . . .
C11 C 0.2728(2) 0.7928(4) 0.8630(7) 0.0595(18) Uani 1 1 d . . . . .
H11 H 0.3096 0.7756 0.8623 0.071 Uiso 1 1 calc R . . . .
C26 C 0.5571(3) 0.2998(3) 0.2319(9) 0.0593(17) Uani 1 1 d . . . . .
H26 H 0.5790 0.2751 0.1487 0.071 Uiso 1 1 calc R . . . .
C5 C 0.1482(2) 0.9990(4) 0.7760(8) 0.0598(18) Uani 1 1 d . . . . .
H5 H 0.1211 0.9672 0.7323 0.072 Uiso 1 1 calc R . . . .
C25 C 0.4999(3) 0.3019(3) 0.2115(8) 0.0575(17) Uani 1 1 d . . . . .
H25 H 0.4829 0.2778 0.1142 0.069 Uiso 1 1 calc R . . . .
C30 C 0.2527(2) 0.3218(4) 0.9573(8) 0.0587(18) Uani 1 1 d . . . . .
C2 C 0.2273(3) 1.0951(4) 0.9024(8) 0.0652(19) Uani 1 1 d . . . . .
H2 H 0.2543 1.1272 0.9449 0.078 Uiso 1 1 calc R . . . .
C1 C 0.2377(3) 1.0224(4) 0.9071(8) 0.0657(19) Uani 1 1 d . . . . .
H1A H 0.2722 1.0064 0.9525 0.079 Uiso 1 1 calc R . . . .
C4 C 0.1374(3) 1.0718(4) 0.7694(8) 0.0645(19) Uani 1 1 d . . . . .
H4 H 0.1035 1.0884 0.7208 0.077 Uiso 1 1 calc R . . . .
C9 C 0.1749(2) 0.7718(4) 0.8754(8) 0.0639(19) Uani 1 1 d . . . . .
H9 H 0.1446 0.7404 0.8824 0.077 Uiso 1 1 calc R . . . .
C3 C 0.1767(3) 1.1199(4) 0.8347(8) 0.0618(18) Uani 1 1 d . . . . .
H3 H 0.1692 1.1688 0.8330 0.074 Uiso 1 1 calc R . . . .
C8 C 0.1653(3) 0.8444(4) 0.8689(8) 0.0646(19) Uani 1 1 d . . . . .
H8 H 0.1285 0.8610 0.8722 0.078 Uiso 1 1 calc R . . . .
C29 C 0.3171(3) 0.3123(4) 0.9773(11) 0.074(2) Uani 1 1 d . . . . .
C33 C 0.0893(2) 0.3553(5) 0.7277(9) 0.092(3) Uani 1 1 d . . . . .
H33A H 0.0896 0.3872 0.6230 0.110 Uiso 1 1 calc R . . . .
H33B H 0.0644 0.3752 0.8185 0.110 Uiso 1 1 calc R . . . .
C34 C 0.0699(3) 0.2823(5) 0.6717(11) 0.124(4) Uani 1 1 d . . . . .
H34A H 0.0338 0.2859 0.6121 0.186 Uiso 1 1 calc GR . . . .
H34B H 0.0669 0.2524 0.7778 0.186 Uiso 1 1 calc GR . . . .
H34C H 0.0964 0.2618 0.5891 0.186 Uiso 1 1 calc GR . . . .
Cl3A Cl 0.0501(2) 0.6496(3) 1.0022(8) 0.1027(17) Uani 0.5 1 d D U P A 2
Cl2A Cl 0.02132(19) 0.5236(3) 0.9271(8) 0.1354(18) Uani 0.5 1 d D U P A 2
Cl1A Cl 0.0288(3) 0.6150(6) 0.6271(10) 0.197(3) Uani 0.5 1 d D U P A 2
Cl1 Cl 0.0528(2) 0.6953(4) 0.6755(10) 0.197(3) Uani 0.5 1 d D U P B 1
C35A C 0.0631(7) 0.5862(8) 0.8065(19) 0.105(4) Uani 0.5 1 d D U P A 2
H35A H 0.1023 0.5725 0.7874 0.126 Uiso 0.5 1 calc R . P A 2
Cl3 Cl 0.0451(5) 0.6151(7) 0.9615(16) 0.288(6) Uani 0.5 1 d D U P B 1
Cl2 Cl 0.0291(2) 0.5448(3) 0.6074(9) 0.135(2) Uani 0.5 1 d D U P B 1
C35 C 0.0679(10) 0.6090(9) 0.734(2) 0.175(6) Uani 0.5 1 d D U P B 1
H35 H 0.1084 0.5995 0.7291 0.210 Uiso 0.5 1 calc R . P B 1


_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
F3 C29 1.325(7) . ?
O2 C16 1.218(6) . ?
F1 C29 1.329(8) . ?
O1 C13 1.248(7) . ?
O4 C32 1.335(8) . ?
O4 C33 1.459(6) . ?
O3 C32 1.216(8) . ?
F2 C29 1.350(8) . ?
O5 C30 1.189(7) . ?
N2 N1 1.327(6) . ?
N2 C31 1.304(7) . ?
N1 H1 0.8600 . ?
N1 C15 1.390(7) . ?
C20 C21 1.382(7) . ?
C20 C23 1.478(7) . ?
C20 C19 1.395(6) . ?
C21 H21 0.9300 . ?
C21 C22 1.369(7) . ?
C28 H28 0.9300 . ?
C28 C23 1.400(7) . ?
C28 C27 1.381(7) . ?
C23 C24 1.390(7) . ?
C17 C22 1.392(7) . ?
C17 C18 1.382(7) . ?
C17 C16 1.471(7) . ?
C19 H19 0.9300 . ?
C19 C18 1.377(7) . ?
C22 H22 0.9300 . ?
C24 H24 0.9300 . ?
C24 C25 1.389(7) . ?
C18 H18 0.9300 . ?
C15 C16 1.522(7) . ?
C15 C14 1.346(8) . ?
C10 C13 1.486(8) . ?
C10 C11 1.374(8) . ?
C10 C9 1.385(7) . ?
C7 C6 1.485(8) . ?
C7 C12 1.394(7) . ?
C7 C8 1.393(8) . ?
C27 H27 0.9300 . ?
C27 C26 1.366(7) . ?
C31 C32 1.481(8) . ?
C31 C30 1.489(8) . ?
C6 C5 1.385(7) . ?
C6 C1 1.394(8) . ?
C14 H14 0.9300 . ?
C14 C13 1.460(8) . ?
C12 H12 0.9300 . ?
C12 C11 1.386(8) . ?
C11 H11 0.9300 . ?
C26 H26 0.9300 . ?
C26 C25 1.367(8) . ?
C5 H5 0.9300 . ?
C5 C4 1.383(8) . ?
C25 H25 0.9300 . ?
C30 C29 1.546(8) . ?
C2 H2 0.9300 . ?
C2 C1 1.378(8) . ?
C2 C3 1.374(8) . ?
C1 H1A 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.376(8) . ?
C9 H9 0.9300 . ?
C9 C8 1.373(8) . ?
C3 H3 0.9300 . ?
C8 H8 0.9300 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C33 C34 1.492(10) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
Cl3A C35A 1.886(15) . ?
Cl2A Cl2A 1.723(9) 3_567 ?
Cl2A C35A 1.776(14) . ?
Cl1A C35A 1.627(14) . ?
Cl1 C35 1.704(17) . ?
C35A H35A 0.9800 . ?
Cl3 C35 1.759(17) . ?
Cl2 C35 1.768(16) . ?
C35 H35 0.9800 . ?

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
C32 O4 C33 116.3(6) . . ?
C31 N2 N1 120.1(5) . . ?
N2 N1 H1 121.2 . . ?
N2 N1 C15 117.5(5) . . ?
C15 N1 H1 121.2 . . ?
C21 C20 C23 122.1(5) . . ?
C21 C20 C19 117.9(5) . . ?
C19 C20 C23 120.0(5) . . ?
C20 C21 H21 119.2 . . ?
C22 C21 C20 121.7(5) . . ?
C22 C21 H21 119.2 . . ?
C23 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C27 C28 C23 120.0(5) . . ?
C28 C23 C20 120.2(5) . . ?
C24 C23 C20 121.8(5) . . ?
C24 C23 C28 118.0(5) . . ?
C22 C17 C16 119.6(5) . . ?
C18 C17 C22 118.9(5) . . ?
C18 C17 C16 121.5(5) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 C20 120.8(5) . . ?
C18 C19 H19 119.6 . . ?
C21 C22 C17 120.2(5) . . ?
C21 C22 H22 119.9 . . ?
C17 C22 H22 119.9 . . ?
C23 C24 H24 119.8 . . ?
C25 C24 C23 120.4(5) . . ?
C25 C24 H24 119.8 . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.5(5) . . ?
C19 C18 H18 119.7 . . ?
N1 C15 C16 116.3(6) . . ?
C14 C15 N1 122.2(5) . . ?
C14 C15 C16 121.4(6) . . ?
O2 C16 C17 123.9(5) . . ?
O2 C16 C15 117.1(5) . . ?
C17 C16 C15 119.0(5) . . ?
C11 C10 C13 124.6(6) . . ?
C11 C10 C9 118.0(6) . . ?
C9 C10 C13 117.4(6) . . ?
C12 C7 C6 121.5(6) . . ?
C8 C7 C6 121.9(5) . . ?
C8 C7 C12 116.6(6) . . ?
C28 C27 H27 119.2 . . ?
C26 C27 C28 121.7(6) . . ?
C26 C27 H27 119.2 . . ?
N2 C31 C32 124.9(7) . . ?
N2 C31 C30 112.7(5) . . ?
C32 C31 C30 122.4(6) . . ?
C5 C6 C7 121.4(6) . . ?
C5 C6 C1 116.6(6) . . ?
C1 C6 C7 122.0(6) . . ?
C15 C14 H14 117.7 . . ?
C15 C14 C13 124.6(6) . . ?
C13 C14 H14 117.7 . . ?
O1 C13 C10 120.3(6) . . ?
O1 C13 C14 119.7(6) . . ?
C14 C13 C10 120.0(6) . . ?
O4 C32 C31 112.9(7) . . ?
O3 C32 O4 124.7(6) . . ?
O3 C32 C31 122.4(7) . . ?
C7 C12 H12 119.5 . . ?
C11 C12 C7 121.0(6) . . ?
C11 C12 H12 119.5 . . ?
C10 C11 C12 121.4(6) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C27 C26 H26 120.6 . . ?
C27 C26 C25 118.9(6) . . ?
C25 C26 H26 120.6 . . ?
C6 C5 H5 119.1 . . ?
C4 C5 C6 121.7(6) . . ?
C4 C5 H5 119.1 . . ?
C24 C25 H25 119.5 . . ?
C26 C25 C24 121.1(6) . . ?
C26 C25 H25 119.5 . . ?
O5 C30 C31 126.2(6) . . ?
O5 C30 C29 117.3(7) . . ?
C31 C30 C29 116.4(6) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C3 C2 C1 119.8(6) . . ?
C6 C1 H1A 118.9 . . ?
C2 C1 C6 122.1(6) . . ?
C2 C1 H1A 118.9 . . ?
C5 C4 H4 119.9 . . ?
C3 C4 C5 120.1(6) . . ?
C3 C4 H4 119.9 . . ?
C10 C9 H9 119.6 . . ?
C8 C9 C10 120.8(6) . . ?
C8 C9 H9 119.6 . . ?
C2 C3 C4 119.6(7) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C7 C8 H8 119.0 . . ?
C9 C8 C7 122.1(6) . . ?
C9 C8 H8 119.0 . . ?
F3 C29 F1 108.7(6) . . ?
F3 C29 F2 106.8(6) . . ?
F3 C29 C30 112.9(6) . . ?
F1 C29 F2 107.0(6) . . ?
F1 C29 C30 112.7(6) . . ?
F2 C29 C30 108.4(6) . . ?
O4 C33 H33A 110.4 . . ?
O4 C33 H33B 110.4 . . ?
O4 C33 C34 106.8(6) . . ?
H33A C33 H33B 108.6 . . ?
C34 C33 H33A 110.4 . . ?
C34 C33 H33B 110.4 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
Cl2A Cl2A C35A 168.8(8) 3_567 . ?
Cl3A C35A H35A 116.0 . . ?
Cl2A C35A Cl3A 86.3(7) . . ?
Cl2A C35A H35A 116.0 . . ?
Cl1A C35A Cl3A 108.8(9) . . ?
Cl1A C35A Cl2A 109.9(10) . . ?
Cl1A C35A H35A 116.0 . . ?
Cl1 C35 Cl3 96.4(10) . . ?
Cl1 C35 Cl2 113.6(12) . . ?
Cl1 C35 H35 111.3 . . ?
Cl3 C35 Cl2 112.0(12) . . ?
Cl3 C35 H35 111.3 . . ?
Cl2 C35 H35 111.3 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_pl
_database_code_depnum_ccdc_archive 'CCDC 2155007'
loop_
_audit_author_name
_audit_author_address
'zheng fang'
;Fuzhou University, Fuzhou City, Fujian Province
China
;
_audit_update_record             
;
2022-02-27 deposited with the CCDC.	2022-04-06 downloaded from the CCDC.
;
_audit_creation_date             2022-02-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H13 F3 N6 O2'
_chemical_formula_sum            'C24 H13 F3 N6 O2'
_chemical_formula_weight         474.40
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.582(3)
_cell_length_b                   12.447(3)
_cell_length_c                   22.472(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4358.4(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2636
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.23
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1021 before and 0.0443 after correction.
The Ratio of minimum to maximum transmission is 0.8031.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1742
_diffrn_reflns_av_unetI/netI     0.1298
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            20284
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         2.235
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1801
_reflns_number_total             3984
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         3984
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2218
_refine_ls_R_factor_gt           0.1079
_refine_ls_restrained_S_all      1.098
_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)+(0.0830P)²+7.7766P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2230
_refine_ls_wR_factor_ref         0.2615
_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 Secondary CH2 refined with riding coordinates:
 C072(H07A,H07B)
2.b Aromatic/amide H refined with riding coordinates:
 C00Z(H00Z), C04H(H04H), C05E(H05E), C05K(H05K), C06B(H06B), C06T(H06T),
 C06Z(H06Z), C070(H070)
2.c Idealised Me refined as rotating group:
 C07O(H07C,H07D,H07E)
;
_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
F001 F -1.0947(2) -0.5012(3) 0.97524(17) 0.0622(11) Uani 1 1 d . . . . .
F00D F -1.1646(2) -0.6443(3) 0.95197(18) 0.0700(12) Uani 1 1 d . . . . .
F00O F -1.0852(3) -0.6411(4) 1.02992(17) 0.0740(13) Uani 1 1 d . . . . .
O00A O -1.0811(3) -0.8529(4) 0.9866(2) 0.0644(14) Uani 1 1 d . . . . .
O044 O -0.9632(3) -0.8401(4) 1.0452(3) 0.0795(17) Uani 1 1 d . . . . .
N013 N -0.8942(4) -0.7692(5) 0.9335(3) 0.0651(17) Uani 1 1 d . . . . .
N015 N -0.9548(3) -0.4284(4) 0.8300(2) 0.0480(14) Uani 1 1 d . . . . .
N02B N -0.8532(3) -0.7069(4) 0.8961(3) 0.0575(16) Uani 1 1 d . . . . .
N02W N -0.4177(4) -0.6366(6) 0.7727(3) 0.080(2) Uani 1 1 d . . . . .
N036 N -0.8694(3) -0.4508(4) 0.8235(2) 0.0483(14) Uani 1 1 d . . . . .
N053 N -1.4230(4) -0.3265(5) 0.8347(3) 0.0710(19) Uani 1 1 d . . . . .
C00N C -1.0978(4) -0.4586(5) 0.8551(3) 0.0437(16) Uani 1 1 d . . . . .
C00T C -0.9717(4) -0.7386(5) 0.9544(3) 0.0464(17) Uani 1 1 d . . . . .
C00Z C -0.6048(4) -0.4977(6) 0.8150(3) 0.0550(19) Uani 1 1 d . . . . .
H00Z H -0.566053 -0.441038 0.816635 0.066 Uiso 1 1 calc R U . . .
C01R C -1.2666(4) -0.3918(6) 0.8418(3) 0.0492(17) Uani 1 1 d . . . . .
C027 C -0.9746(4) -0.5842(4) 0.8912(3) 0.0378(15) Uani 1 1 d . . . . .
C03C C -1.0905(4) -0.6071(7) 0.9725(3) 0.0564(19) Uani 1 1 d . . . . .
C03N C -1.0038(5) -0.8165(6) 1.0014(4) 0.0556(18) Uani 1 1 d . . . . .
C03P C -0.5779(4) -0.6008(6) 0.7988(3) 0.0461(17) Uani 1 1 d . . . . .
C03R C -0.4873(5) -0.6204(6) 0.7839(3) 0.061(2) Uani 1 1 d . . . . .
C04H C -0.6898(4) -0.4823(5) 0.8284(3) 0.0463(17) Uani 1 1 d . . . . .
H04H H -0.708488 -0.414163 0.839434 0.056 Uiso 1 1 calc R U . . .
C04X C -1.0063(4) -0.4914(5) 0.8601(3) 0.0420(16) Uani 1 1 d . . . . .
C054 C -0.8908(4) -0.6176(5) 0.8753(3) 0.0398(16) Uani 1 1 d . . . . .
C05E C -0.6347(4) -0.6839(5) 0.7955(3) 0.0458(17) Uani 1 1 d . . . . .
H05E H -0.615496 -0.752044 0.784954 0.055 Uiso 1 1 calc R U . . .
C05K C -1.2039(4) -0.3183(5) 0.8587(3) 0.058(2) Uani 1 1 d . . . . .
H05K H -1.218414 -0.247125 0.866119 0.069 Uiso 1 1 calc R U . . .
C05M C -0.7491(4) -0.5670(5) 0.8258(3) 0.0405(16) Uani 1 1 d . . . . .
C068 C -1.3546(5) -0.3563(6) 0.8375(3) 0.0558(19) Uani 1 1 d . . . . .
C06B C -1.2447(4) -0.4971(6) 0.8317(3) 0.0484(17) Uani 1 1 d . . . . .
H06B H -1.286565 -0.546034 0.820117 0.058 Uiso 1 1 calc R U . . .
C06O C -1.0129(4) -0.6466(5) 0.9374(3) 0.0432(16) Uani 1 1 d . . . . .
C06T C -1.1612(4) -0.5305(5) 0.8387(3) 0.0434(16) Uani 1 1 d . . . . .
H06T H -1.147287 -0.602234 0.832364 0.052 Uiso 1 1 calc R U . . .
C06Z C -0.7199(4) -0.6674(5) 0.8075(3) 0.0462(17) Uani 1 1 d . . . . .
H06Z H -0.758555 -0.723850 0.803445 0.055 Uiso 1 1 calc R U . . .
C070 C -1.1206(4) -0.3519(6) 0.8642(3) 0.059(2) Uani 1 1 d . . . . .
H070 H -1.078391 -0.302333 0.874292 0.071 Uiso 1 1 calc R U . . .
C072 C -1.1219(5) -0.9233(7) 1.0318(4) 0.085(3) Uani 1 1 d . . . . .
H07A H -1.084951 -0.983955 1.040727 0.102 Uiso 1 1 calc R U . . .
H07B H -1.132151 -0.883652 1.068225 0.102 Uiso 1 1 calc R U . . .
C07M C -0.8397(4) -0.5450(5) 0.8410(3) 0.0421(16) Uani 1 1 d . . . . .
C07O C -1.2028(6) -0.9604(10) 1.0064(4) 0.137(5) Uani 1 1 d . . . . .
H07C H -1.191764 -0.998256 0.969996 0.206 Uiso 1 1 calc R U . . .
H07D H -1.239081 -0.899695 0.998454 0.206 Uiso 1 1 calc R U . . .
H07E H -1.230822 -1.007484 1.034082 0.206 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
F001 C03C 1.321(8) . ?
F00D C03C 1.327(7) . ?
F00O C03C 1.361(8) . ?
O00A C03N 1.329(8) . ?
O00A C072 1.484(8) . ?
O044 C03N 1.207(8) . ?
N013 N02B 1.310(7) . ?
N013 C00T 1.350(8) . ?
N015 N036 1.369(7) . ?
N015 C04X 1.310(7) . ?
N02B C054 1.341(7) . ?
N02W C03R 1.131(8) . ?
N036 C07M 1.320(7) . ?
N053 C068 1.131(8) . ?
C00N C04X 1.488(8) . ?
C00N C06T 1.383(8) . ?
C00N C070 1.390(9) . ?
C00T C03N 1.519(9) . ?
C00T C06O 1.367(8) . ?
C00Z H00Z 0.9300 . ?
C00Z C03P 1.398(9) . ?
C00Z C04H 1.371(8) . ?
C01R C05K 1.391(9) . ?
C01R C068 1.442(9) . ?
C01R C06B 1.373(9) . ?
C027 C04X 1.437(8) . ?
C027 C054 1.416(8) . ?
C027 C06O 1.428(8) . ?
C03C C06O 1.524(9) . ?
C03P C03R 1.472(10) . ?
C03P C05E 1.362(8) . ?
C04H H04H 0.9300 . ?
C04H C05M 1.403(8) . ?
C054 C07M 1.431(8) . ?
C05E H05E 0.9300 . ?
C05E C06Z 1.370(8) . ?
C05K H05K 0.9300 . ?
C05K C070 1.370(9) . ?
C05M C06Z 1.393(8) . ?
C05M C07M 1.478(8) . ?
C06B H06B 0.9300 . ?
C06B C06T 1.374(8) . ?
C06T H06T 0.9300 . ?
C06Z H06Z 0.9300 . ?
C070 H070 0.9300 . ?
C072 H07A 0.9700 . ?
C072 H07B 0.9700 . ?
C072 C07O 1.459(10) . ?
C07O H07C 0.9600 . ?
C07O H07D 0.9600 . ?
C07O H07E 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
C03N O00A C072 114.8(6) . . ?
N02B N013 C00T 119.5(6) . . ?
C04X N015 N036 121.9(5) . . ?
N013 N02B C054 120.1(5) . . ?
C07M N036 N015 119.3(5) . . ?
C06T C00N C04X 121.9(5) . . ?
C06T C00N C070 118.3(6) . . ?
C070 C00N C04X 119.7(6) . . ?
N013 C00T C03N 110.8(6) . . ?
N013 C00T C06O 124.1(6) . . ?
C06O C00T C03N 125.1(6) . . ?
C03P C00Z H00Z 120.8 . . ?
C04H C00Z H00Z 120.8 . . ?
C04H C00Z C03P 118.4(6) . . ?
C05K C01R C068 119.0(6) . . ?
C06B C01R C05K 119.8(6) . . ?
C06B C01R C068 121.2(6) . . ?
C054 C027 C04X 115.5(5) . . ?
C054 C027 C06O 114.2(5) . . ?
C06O C027 C04X 130.3(6) . . ?
F001 C03C F00D 108.8(6) . . ?
F001 C03C F00O 105.5(6) . . ?
F001 C03C C06O 112.7(6) . . ?
F00D C03C F00O 105.9(5) . . ?
F00D C03C C06O 113.5(6) . . ?
F00O C03C C06O 110.0(6) . . ?
O00A C03N C00T 110.0(6) . . ?
O044 C03N O00A 126.6(7) . . ?
O044 C03N C00T 123.4(7) . . ?
C00Z C03P C03R 119.9(6) . . ?
C05E C03P C00Z 121.1(6) . . ?
C05E C03P C03R 118.9(6) . . ?
N02W C03R C03P 179.2(8) . . ?
C00Z C04H H04H 119.3 . . ?
C00Z C04H C05M 121.4(6) . . ?
C05M C04H H04H 119.3 . . ?
N015 C04X C00N 112.5(5) . . ?
N015 C04X C027 121.4(5) . . ?
C027 C04X C00N 126.0(5) . . ?
N02B C054 C027 124.0(5) . . ?
N02B C054 C07M 117.9(6) . . ?
C027 C054 C07M 117.6(5) . . ?
C03P C05E H05E 119.9 . . ?
C03P C05E C06Z 120.3(6) . . ?
C06Z C05E H05E 119.9 . . ?
C01R C05K H05K 120.3 . . ?
C070 C05K C01R 119.4(6) . . ?
C070 C05K H05K 120.3 . . ?
C04H C05M C07M 118.7(6) . . ?
C06Z C05M C04H 118.1(5) . . ?
C06Z C05M C07M 123.1(6) . . ?
N053 C068 C01R 178.5(8) . . ?
C01R C06B H06B 119.8 . . ?
C01R C06B C06T 120.4(6) . . ?
C06T C06B H06B 119.8 . . ?
C00T C06O C027 117.5(6) . . ?
C00T C06O C03C 119.9(6) . . ?
C027 C06O C03C 122.1(6) . . ?
C00N C06T H06T 119.6 . . ?
C06B C06T C00N 120.7(6) . . ?
C06B C06T H06T 119.6 . . ?
C05E C06Z C05M 120.6(6) . . ?
C05E C06Z H06Z 119.7 . . ?
C05M C06Z H06Z 119.7 . . ?
C00N C070 H070 119.3 . . ?
C05K C070 C00N 121.4(6) . . ?
C05K C070 H070 119.3 . . ?
O00A C072 H07A 110.3 . . ?
O00A C072 H07B 110.3 . . ?
H07A C072 H07B 108.6 . . ?
C07O C072 O00A 106.9(7) . . ?
C07O C072 H07A 110.3 . . ?
C07O C072 H07B 110.3 . . ?
N036 C07M C054 121.8(6) . . ?
N036 C07M C05M 115.5(5) . . ?
C054 C07M C05M 122.7(6) . . ?
C072 C07O H07C 109.5 . . ?
C072 C07O H07D 109.5 . . ?
C072 C07O H07E 109.5 . . ?
H07C C07O H07D 109.5 . . ?
H07C C07O H07E 109.5 . . ?
H07D C07O H07E 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
F001 C03C C06O C00T 144.7(6) . . . . ?
F001 C03C C06O C027 -27.5(9) . . . . ?
F00D C03C C06O C00T -91.1(8) . . . . ?
F00D C03C C06O C027 96.7(8) . . . . ?
F00O C03C C06O C00T 27.3(8) . . . . ?
F00O C03C C06O C027 -144.9(6) . . . . ?
N013 N02B C054 C027 0.1(10) . . . . ?
N013 N02B C054 C07M 171.8(6) . . . . ?
N013 C00T C03N O00A -125.1(6) . . . . ?
N013 C00T C03N O044 54.8(9) . . . . ?
N013 C00T C06O C027 5.3(10) . . . . ?
N013 C00T C06O C03C -167.3(6) . . . . ?
N015 N036 C07M C054 -10.3(9) . . . . ?
N015 N036 C07M C05M 173.1(5) . . . . ?
N02B N013 C00T C03N -174.4(6) . . . . ?
N02B N013 C00T C06O 2.4(10) . . . . ?
N02B C054 C07M N036 -173.7(6) . . . . ?
N02B C054 C07M C05M 2.7(9) . . . . ?
N036 N015 C04X C00N -172.9(5) . . . . ?
N036 N015 C04X C027 4.2(9) . . . . ?
C00T N013 N02B C054 -5.1(10) . . . . ?
C00Z C03P C05E C06Z 0.5(10) . . . . ?
C00Z C04H C05M C06Z -1.8(9) . . . . ?
C00Z C04H C05M C07M 179.8(6) . . . . ?
C01R C05K C070 C00N -2.0(11) . . . . ?
C01R C06B C06T C00N -1.0(10) . . . . ?
C027 C054 C07M N036 -1.4(9) . . . . ?
C027 C054 C07M C05M 174.9(6) . . . . ?
C03N O00A C072 C07O -176.5(8) . . . . ?
C03N C00T C06O C027 -178.3(6) . . . . ?
C03N C00T C06O C03C 9.1(10) . . . . ?
C03P C00Z C04H C05M -0.4(10) . . . . ?
C03P C05E C06Z C05M -2.8(10) . . . . ?
C03R C03P C05E C06Z -178.2(6) . . . . ?
C04H C00Z C03P C03R 179.7(6) . . . . ?
C04H C00Z C03P C05E 1.0(10) . . . . ?
C04H C05M C06Z C05E 3.3(9) . . . . ?
C04H C05M C07M N036 37.2(8) . . . . ?
C04H C05M C07M C054 -139.3(6) . . . . ?
C04X N015 N036 C07M 9.1(9) . . . . ?
C04X C00N C06T C06B -177.0(6) . . . . ?
C04X C00N C070 C05K 178.6(6) . . . . ?
C04X C027 C054 N02B -174.7(6) . . . . ?
C04X C027 C054 C07M 13.6(8) . . . . ?
C04X C027 C06O C00T 172.9(6) . . . . ?
C04X C027 C06O C03C -14.8(10) . . . . ?
C054 C027 C04X N015 -15.3(8) . . . . ?
C054 C027 C04X C00N 161.3(6) . . . . ?
C054 C027 C06O C00T -9.4(8) . . . . ?
C054 C027 C06O C03C 163.0(6) . . . . ?
C05K C01R C06B C06T 0.5(10) . . . . ?
C068 C01R C05K C070 178.5(6) . . . . ?
C068 C01R C06B C06T -177.0(6) . . . . ?
C06B C01R C05K C070 0.9(10) . . . . ?
C06O C00T C03N O00A 58.1(9) . . . . ?
C06O C00T C03N O044 -121.9(8) . . . . ?
C06O C027 C04X N015 162.4(6) . . . . ?
C06O C027 C04X C00N -20.9(10) . . . . ?
C06O C027 C054 N02B 7.2(9) . . . . ?
C06O C027 C054 C07M -164.5(5) . . . . ?
C06T C00N C04X N015 128.3(6) . . . . ?
C06T C00N C04X C027 -48.7(9) . . . . ?
C06T C00N C070 C05K 1.5(10) . . . . ?
C06Z C05M C07M N036 -141.1(6) . . . . ?
C06Z C05M C07M C054 42.3(9) . . . . ?
C070 C00N C04X N015 -48.7(8) . . . . ?
C070 C00N C04X C027 134.4(7) . . . . ?
C070 C00N C06T C06B 0.0(10) . . . . ?
C072 O00A C03N O044 4.6(11) . . . . ?
C072 O00A C03N C00T -175.4(6) . . . . ?
C07M C05M C06Z C05E -178.3(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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 2102384'
loop_
_audit_author_name
_audit_author_address
'fang zheng'
;Fuzhou University
China
;
_audit_update_record             
;
2022-01-11 deposited with the CCDC.	2022-04-06 downloaded from the CCDC.
;
_audit_creation_date             2022-01-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H15 F3 N2 O4'
_chemical_formula_sum            'C22 H15 F3 N2 O4'
_chemical_formula_weight         428.36
_chemical_absolute_configuration ?
_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           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   28.4017(14)
_cell_length_b                   10.6516(5)
_cell_length_c                   14.9143(8)
_cell_angle_alpha                90
_cell_angle_beta                 116.751(2)
_cell_angle_gamma                90
_cell_volume                     4029.0(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9958
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.763
_cell_measurement_theta_min      2.353
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0739 before and 0.0623 after correction.
The Ratio of minimum to maximum transmission is 0.9320.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0691
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            63913
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.064
_diffrn_reflns_theta_max         25.064
_diffrn_reflns_theta_min         2.074
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.996
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                6492
_reflns_number_total             7127
_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       lb20201022
_computing_data_collection       ?
_computing_data_reduction        lb20201022
_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    ?
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 2888 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     561
_refine_ls_number_reflns         7127
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0376
_refine_ls_restrained_S_all      1.048
_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)+(0.0671P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1007
_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 Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B), C48(H48A,H48B)
2.b Aromatic/amide H refined with riding coordinates:
 C31(H31), C32(H32), C34(H34), C35(H35), C41(H41), C42(H42), C45(H45),
 C46(H46), C47(H47), C49(H49), C50(H50), C51(H51), C52(H52), C53(H53), C54(H54),
  C56(H56), C57(H57), C58(H58), C60(H60), C61(H61)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.43540(9) 0.41883(19) 0.33519(15) 0.0436(5) Uani 1 1 d . . . . .
F4 F 0.02505(9) 1.5289(2) 0.14532(15) 0.0443(5) Uani 1 1 d . . . . .
F5 F -0.03270(8) 1.4842(2) 0.19485(17) 0.0481(5) Uani 1 1 d . . . . .
F2 F 0.49188(8) 0.4451(2) 0.27871(17) 0.0484(6) Uani 1 1 d . . . . .
F6 F 0.02816(9) 1.61792(19) 0.27705(17) 0.0470(5) Uani 1 1 d . . . . .
F3 F 0.42690(9) 0.32062(17) 0.20271(17) 0.0478(5) Uani 1 1 d . . . . .
O4 O 0.13953(12) 1.5629(2) 0.2740(2) 0.0448(7) Uani 1 1 d . . . . .
O6 O 0.21029(10) 1.3163(2) 0.3674(2) 0.0458(7) Uani 1 1 d . . . . .
O2 O 0.31960(11) 0.3934(2) 0.2052(2) 0.0440(6) Uani 1 1 d . . . . .
O1 O 0.25323(10) 0.6500(2) 0.1148(2) 0.0431(6) Uani 1 1 d . . . . .
O3 O 0.51444(10) 0.6486(3) 0.1572(2) 0.0488(7) Uani 1 1 d . . . . .
O5 O -0.04753(10) 1.2711(3) 0.3313(2) 0.0497(7) Uani 1 1 d . . . . .
O7 O -0.01178(9) 1.4572(2) 0.39931(18) 0.0366(6) Uani 1 1 d . . . . .
O8 O 0.46999(10) 0.4827(2) 0.06409(19) 0.0385(6) Uani 1 1 d . . . . .
N2 N 0.40070(12) 0.7086(3) 0.0758(2) 0.0365(7) Uani 1 1 d . . . . .
N1 N 0.06303(11) 1.2259(3) 0.3961(2) 0.0337(7) Uani 1 1 d . . . . .
C15 C 0.33518(14) 0.4973(3) 0.2383(3) 0.0305(7) Uani 1 1 d . . . . .
C16 C 0.17922(14) 1.2310(3) 0.3503(3) 0.0332(8) Uani 1 1 d . . . . .
C17 C 0.36162(13) 0.5746(3) 0.1874(2) 0.0288(7) Uani 1 1 d . . . . .
N4 N 0.35657(11) 0.7474(3) 0.0783(2) 0.0351(7) Uani 1 1 d . . . . .
C19 C 0.33786(13) 0.6832(3) 0.1320(2) 0.0279(7) Uani 1 1 d . . . . .
C20 C 0.40860(12) 0.5382(3) 0.1872(2) 0.0276(7) Uani 1 1 d . . . . .
C21 C 0.12495(13) 1.4595(3) 0.2387(3) 0.0323(8) Uani 1 1 d . . . . .
C22 C 0.01879(14) 1.5095(3) 0.2271(3) 0.0356(8) Uani 1 1 d . . . . .
C23 C 0.12912(13) 1.4109(3) 0.1500(3) 0.0296(7) Uani 1 1 d . . . . .
C24 C 0.05318(13) 1.4040(3) 0.2895(2) 0.0286(7) Uani 1 1 d . . . . .
N3 N 0.10773(11) 1.1941(3) 0.3921(2) 0.0348(7) Uani 1 1 d . . . . .
C27 C 0.42591(13) 0.6090(3) 0.1291(3) 0.0303(7) Uani 1 1 d . . . . .
C28 C 0.32986(13) 0.5523(3) 0.3242(2) 0.0272(7) Uani 1 1 d . . . . .
C29 C 0.47578(14) 0.5827(3) 0.1201(3) 0.0322(8) Uani 1 1 d . . . . .
C30 C 0.10019(13) 1.3759(3) 0.2892(2) 0.0262(7) Uani 1 1 d . . . . .
C31 C 0.22470(14) 0.9046(4) 0.0975(3) 0.0404(9) Uani 1 1 d . . . . .
H31 H 0.197751 0.845486 0.077002 0.049 Uiso 1 1 calc R . . . .
C32 C 0.35888(13) 0.6568(3) 0.3748(2) 0.0298(7) Uani 1 1 d . . . . .
H32 H 0.381522 0.695157 0.353492 0.036 Uiso 1 1 calc R . . . .
C33 C 0.51485(16) 0.4393(4) 0.0492(3) 0.0428(9) Uani 1 1 d . . . . .
H33A H 0.543989 0.497767 0.079724 0.051 Uiso 1 1 calc R . . . .
H33B H 0.505007 0.434127 -0.022012 0.051 Uiso 1 1 calc R . . . .
C34 C 0.35412(14) 0.7038(3) 0.4565(3) 0.0336(8) Uani 1 1 d . . . . .
H34 H 0.373877 0.773136 0.490928 0.040 Uiso 1 1 calc R . . . .
C35 C 0.31609(14) 0.9544(3) 0.1585(3) 0.0386(8) Uani 1 1 d . . . . .
H35 H 0.350596 0.929338 0.176950 0.046 Uiso 1 1 calc R . . . .
C36 C 0.12584(13) 1.2670(3) 0.3416(2) 0.0288(7) Uani 1 1 d . . . . .
C37 C 0.27615(13) 0.8655(3) 0.1264(2) 0.0315(7) Uani 1 1 d . . . . .
C38 C 0.28566(13) 0.7294(3) 0.1233(2) 0.0300(7) Uani 1 1 d . . . . .
C39 C 0.19212(13) 1.0993(3) 0.3406(2) 0.0322(7) Uani 1 1 d . . . . .
C41 C 0.10141(13) 1.3040(3) 0.0992(3) 0.0332(8) Uani 1 1 d . . . . .
H41 H 0.080973 1.259960 0.122869 0.040 Uiso 1 1 calc R . . . .
C42 C 0.10444(15) 1.2637(3) 0.0136(3) 0.0376(8) Uani 1 1 d . . . . .
H42 H 0.085572 1.193389 -0.020977 0.045 Uiso 1 1 calc R . . . .
C43 C -0.01299(13) 1.3477(3) 0.3572(3) 0.0313(7) Uani 1 1 d . . . . .
C44 C 0.03667(13) 1.3270(3) 0.3463(3) 0.0291(7) Uani 1 1 d . . . . .
C45 C 0.16022(14) 1.4751(3) 0.1144(3) 0.0364(8) Uani 1 1 d . . . . .
H45 H 0.178794 1.546370 0.147685 0.044 Uiso 1 1 calc R . . . .
C46 C 0.30511(17) 1.0796(3) 0.1634(3) 0.0470(10) Uani 1 1 d . . . . .
H46 H 0.332253 1.138316 0.187213 0.056 Uiso 1 1 calc R . . . .
C47 C 0.29579(13) 0.4947(3) 0.3554(3) 0.0326(8) Uani 1 1 d . . . . .
H47 H 0.276733 0.423832 0.322345 0.039 Uiso 1 1 calc R . . . .
C48 C -0.05879(15) 1.4908(4) 0.4102(3) 0.0453(9) Uani 1 1 d . . . . .
H48A H -0.059129 1.447263 0.467027 0.054 Uiso 1 1 calc R . . . .
H48B H -0.090387 1.468306 0.350163 0.054 Uiso 1 1 calc R . . . .
C49 C 0.31983(13) 0.6474(3) 0.4873(3) 0.0342(8) Uani 1 1 d . . . . .
H49 H 0.316518 0.679033 0.542303 0.041 Uiso 1 1 calc R . . . .
C50 C 0.16337(15) 1.4331(4) 0.0302(3) 0.0402(9) Uani 1 1 d . . . . .
H50 H 0.184368 1.475799 0.007173 0.048 Uiso 1 1 calc R . . . .
C51 C 0.29066(14) 0.5445(3) 0.4364(3) 0.0349(8) Uani 1 1 d . . . . .
H51 H 0.267249 0.508049 0.456619 0.042 Uiso 1 1 calc R . . . .
C52 C 0.21306(17) 1.0309(4) 0.0989(3) 0.0519(11) Uani 1 1 d . . . . .
H52 H 0.178386 1.056948 0.077174 0.062 Uiso 1 1 calc R . . . .
C53 C 0.13579(14) 1.3287(4) -0.0203(3) 0.0426(9) Uani 1 1 d . . . . .
H53 H 0.138108 1.301312 -0.077393 0.051 Uiso 1 1 calc R . . . .
C54 C 0.22124(18) 0.8563(4) 0.3219(3) 0.0534(11) Uani 1 1 d . . . . .
H54 H 0.230942 0.774834 0.314926 0.064 Uiso 1 1 calc R . . . .
C55 C 0.44085(15) 0.4302(3) 0.2507(3) 0.0352(8) Uani 1 1 d . . . . .
C56 C 0.25907(17) 0.9475(4) 0.3622(3) 0.0541(11) Uani 1 1 d . . . . .
H56 H 0.294359 0.927149 0.383729 0.065 Uiso 1 1 calc R . . . .
C57 C 0.15402(15) 1.0060(3) 0.3008(3) 0.0375(8) Uani 1 1 d . . . . .
H57 H 0.118709 1.025079 0.280444 0.045 Uiso 1 1 calc R . . . .
C58 C 0.16870(17) 0.8846(4) 0.2916(3) 0.0477(10) Uani 1 1 d . . . . .
H58 H 0.143249 0.822055 0.264946 0.057 Uiso 1 1 calc R . . . .
C60 C 0.25363(17) 1.1175(4) 0.1329(3) 0.0529(11) Uani 1 1 d . . . . .
H60 H 0.246200 1.202095 0.135177 0.064 Uiso 1 1 calc R . . . .
C61 C 0.24517(15) 1.0696(4) 0.3711(3) 0.0424(9) Uani 1 1 d . . . . .
H61 H 0.270884 1.131607 0.397213 0.051 Uiso 1 1 calc R . . . .
C1 C 0.53073(18) 0.3144(4) 0.0959(4) 0.0553(11) Uani 1 1 d . . . . .
H1A H 0.501642 0.257246 0.065442 0.083 Uiso 1 1 calc GR . . . .
H1B H 0.540919 0.320607 0.166487 0.083 Uiso 1 1 calc GR . . . .
H1C H 0.559948 0.284080 0.086253 0.083 Uiso 1 1 calc GR . . . .
C2 C -0.0564(3) 1.6299(5) 0.4264(5) 0.0789(16) Uani 1 1 d . . . . .
H2A H -0.064390 1.672067 0.364313 0.118 Uiso 1 1 calc GR . . . .
H2B H -0.021606 1.652968 0.475614 0.118 Uiso 1 1 calc GR . . . .
H2C H -0.081571 1.653791 0.449709 0.118 Uiso 1 1 calc GR . . . .


_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 C55 1.342(4) . ?
F4 C22 1.326(4) . ?
F5 C22 1.345(4) . ?
F2 C55 1.325(4) . ?
F6 C22 1.334(4) . ?
F3 C55 1.333(4) . ?
O4 C21 1.210(4) . ?
O6 C16 1.211(4) . ?
O2 C15 1.211(4) . ?
O1 C38 1.214(4) . ?
O3 C29 1.207(4) . ?
O5 C43 1.199(4) . ?
O7 C43 1.317(4) . ?
O7 C48 1.460(4) . ?
O8 C29 1.317(4) . ?
O8 C33 1.464(4) . ?
N2 N4 1.336(4) . ?
N2 C27 1.326(5) . ?
N1 N3 1.341(4) . ?
N1 C44 1.331(4) . ?
C15 C17 1.527(4) . ?
C15 C28 1.478(5) . ?
C16 C36 1.512(5) . ?
C16 C39 1.473(5) . ?
C17 C19 1.405(5) . ?
C17 C20 1.391(5) . ?
N4 C19 1.332(4) . ?
C19 C38 1.511(5) . ?
C20 C27 1.394(5) . ?
C20 C55 1.510(5) . ?
C21 C23 1.475(5) . ?
C21 C30 1.527(4) . ?
C22 C24 1.505(5) . ?
C23 C41 1.398(5) . ?
C23 C45 1.397(5) . ?
C24 C30 1.370(5) . ?
C24 C44 1.402(5) . ?
N3 C36 1.335(4) . ?
C27 C29 1.508(5) . ?
C28 C32 1.388(5) . ?
C28 C47 1.390(5) . ?
C30 C36 1.406(5) . ?
C31 C37 1.388(5) . ?
C31 C52 1.388(6) . ?
C32 C34 1.380(5) . ?
C33 C1 1.475(6) . ?
C34 C49 1.386(5) . ?
C35 C37 1.387(5) . ?
C35 C46 1.379(5) . ?
C37 C38 1.479(5) . ?
C39 C57 1.391(5) . ?
C39 C61 1.400(5) . ?
C41 C42 1.386(5) . ?
C42 C53 1.391(5) . ?
C43 C44 1.507(5) . ?
C45 C50 1.373(5) . ?
C46 C60 1.381(6) . ?
C47 C51 1.386(5) . ?
C48 C2 1.498(7) . ?
C49 C51 1.377(5) . ?
C50 C53 1.374(5) . ?
C52 C60 1.382(7) . ?
C54 C56 1.371(6) . ?
C54 C58 1.384(6) . ?
C56 C61 1.383(6) . ?
C57 C58 1.385(5) . ?

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
C43 O7 C48 116.2(3) . . ?
C29 O8 C33 118.9(3) . . ?
C27 N2 N4 119.4(3) . . ?
C44 N1 N3 119.0(3) . . ?
O2 C15 C17 117.4(3) . . ?
O2 C15 C28 123.7(3) . . ?
C28 C15 C17 118.9(3) . . ?
O6 C16 C36 115.8(3) . . ?
O6 C16 C39 123.0(3) . . ?
C39 C16 C36 121.1(3) . . ?
C19 C17 C15 121.5(3) . . ?
C20 C17 C15 122.5(3) . . ?
C20 C17 C19 115.8(3) . . ?
C19 N4 N2 119.4(3) . . ?
C17 C19 C38 120.8(3) . . ?
N4 C19 C17 124.0(3) . . ?
N4 C19 C38 115.0(3) . . ?
C17 C20 C27 117.2(3) . . ?
C17 C20 C55 121.5(3) . . ?
C27 C20 C55 121.2(3) . . ?
O4 C21 C23 124.0(3) . . ?
O4 C21 C30 117.3(3) . . ?
C23 C21 C30 118.6(3) . . ?
F4 C22 F5 106.1(3) . . ?
F4 C22 F6 107.6(3) . . ?
F4 C22 C24 111.5(3) . . ?
F5 C22 C24 111.7(3) . . ?
F6 C22 F5 106.6(3) . . ?
F6 C22 C24 112.9(3) . . ?
C41 C23 C21 121.2(3) . . ?
C45 C23 C21 119.3(3) . . ?
C45 C23 C41 119.4(3) . . ?
C30 C24 C22 121.6(3) . . ?
C30 C24 C44 117.7(3) . . ?
C44 C24 C22 120.6(3) . . ?
C36 N3 N1 119.4(3) . . ?
N2 C27 C20 124.0(3) . . ?
N2 C27 C29 111.7(3) . . ?
C20 C27 C29 124.3(3) . . ?
C32 C28 C15 121.4(3) . . ?
C32 C28 C47 120.3(3) . . ?
C47 C28 C15 118.2(3) . . ?
O3 C29 O8 126.1(3) . . ?
O3 C29 C27 123.2(3) . . ?
O8 C29 C27 110.6(3) . . ?
C24 C30 C21 122.7(3) . . ?
C24 C30 C36 116.1(3) . . ?
C36 C30 C21 121.1(3) . . ?
C52 C31 C37 120.7(4) . . ?
C34 C32 C28 120.0(3) . . ?
O8 C33 C1 108.4(3) . . ?
C32 C34 C49 119.9(3) . . ?
C46 C35 C37 120.6(4) . . ?
N3 C36 C16 115.5(3) . . ?
N3 C36 C30 124.0(3) . . ?
C30 C36 C16 120.4(3) . . ?
C31 C37 C38 117.7(3) . . ?
C35 C37 C31 119.1(3) . . ?
C35 C37 C38 123.2(3) . . ?
O1 C38 C19 116.8(3) . . ?
O1 C38 C37 123.0(3) . . ?
C37 C38 C19 120.1(3) . . ?
C57 C39 C16 122.9(3) . . ?
C57 C39 C61 119.6(3) . . ?
C61 C39 C16 117.5(3) . . ?
C42 C41 C23 119.9(3) . . ?
C41 C42 C53 119.8(3) . . ?
O5 C43 O7 126.8(3) . . ?
O5 C43 C44 122.3(3) . . ?
O7 C43 C44 110.9(3) . . ?
N1 C44 C24 123.6(3) . . ?
N1 C44 C43 112.1(3) . . ?
C24 C44 C43 124.3(3) . . ?
C50 C45 C23 120.0(3) . . ?
C35 C46 C60 119.7(4) . . ?
C51 C47 C28 118.9(3) . . ?
O7 C48 C2 106.4(4) . . ?
C51 C49 C34 120.0(3) . . ?
C45 C50 C53 120.6(3) . . ?
C49 C51 C47 120.8(3) . . ?
C60 C52 C31 119.2(4) . . ?
C50 C53 C42 120.3(3) . . ?
C56 C54 C58 120.4(4) . . ?
F1 C55 C20 111.3(3) . . ?
F2 C55 F1 106.7(3) . . ?
F2 C55 F3 107.0(3) . . ?
F2 C55 C20 112.0(3) . . ?
F3 C55 F1 107.1(3) . . ?
F3 C55 C20 112.3(3) . . ?
C54 C56 C61 120.5(4) . . ?
C58 C57 C39 119.9(4) . . ?
C54 C58 C57 120.0(4) . . ?
C46 C60 C52 120.7(4) . . ?
C56 C61 C39 119.6(4) . . ?

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
F4 C22 C24 C30 28.7(4) . . . . ?
F4 C22 C24 C44 -148.1(3) . . . . ?
F5 C22 C24 C30 147.2(3) . . . . ?
F5 C22 C24 C44 -29.6(4) . . . . ?
F6 C22 C24 C30 -92.7(4) . . . . ?
F6 C22 C24 C44 90.5(4) . . . . ?
O4 C21 C23 C41 -165.4(4) . . . . ?
O4 C21 C23 C45 12.8(6) . . . . ?
O4 C21 C30 C24 65.9(5) . . . . ?
O4 C21 C30 C36 -111.7(4) . . . . ?
O6 C16 C36 N3 -133.6(3) . . . . ?
O6 C16 C36 C30 42.1(5) . . . . ?
O6 C16 C39 C57 -166.1(4) . . . . ?
O6 C16 C39 C61 12.3(5) . . . . ?
O2 C15 C17 C19 111.8(4) . . . . ?
O2 C15 C17 C20 -64.0(5) . . . . ?
O2 C15 C28 C32 164.2(3) . . . . ?
O2 C15 C28 C47 -14.2(5) . . . . ?
O5 C43 C44 N1 -59.3(5) . . . . ?
O5 C43 C44 C24 120.0(4) . . . . ?
O7 C43 C44 N1 119.7(3) . . . . ?
O7 C43 C44 C24 -61.0(4) . . . . ?
N2 N4 C19 C17 -0.3(5) . . . . ?
N2 N4 C19 C38 -175.6(3) . . . . ?
N2 C27 C29 O3 70.5(4) . . . . ?
N2 C27 C29 O8 -107.2(3) . . . . ?
N1 N3 C36 C16 173.9(3) . . . . ?
N1 N3 C36 C30 -1.6(5) . . . . ?
C15 C17 C19 N4 -173.4(3) . . . . ?
C15 C17 C19 C38 1.7(5) . . . . ?
C15 C17 C20 C27 173.2(3) . . . . ?
C15 C17 C20 C55 -9.5(5) . . . . ?
C15 C28 C32 C34 -178.2(3) . . . . ?
C15 C28 C47 C51 179.5(3) . . . . ?
C16 C39 C57 C58 178.4(4) . . . . ?
C16 C39 C61 C56 -179.2(4) . . . . ?
C17 C15 C28 C32 -15.9(5) . . . . ?
C17 C15 C28 C47 165.7(3) . . . . ?
C17 C19 C38 O1 -38.3(4) . . . . ?
C17 C19 C38 C37 141.1(3) . . . . ?
C17 C20 C27 N2 0.9(5) . . . . ?
C17 C20 C27 C29 -179.9(3) . . . . ?
C17 C20 C55 F1 -30.6(4) . . . . ?
C17 C20 C55 F2 -150.0(3) . . . . ?
C17 C20 C55 F3 89.5(4) . . . . ?
N4 N2 C27 C20 1.6(5) . . . . ?
N4 N2 C27 C29 -177.8(3) . . . . ?
N4 C19 C38 O1 137.1(3) . . . . ?
N4 C19 C38 C37 -43.5(4) . . . . ?
C19 C17 C20 C27 -2.8(4) . . . . ?
C19 C17 C20 C55 174.5(3) . . . . ?
C20 C17 C19 N4 2.7(5) . . . . ?
C20 C17 C19 C38 177.7(3) . . . . ?
C20 C27 C29 O3 -108.8(4) . . . . ?
C20 C27 C29 O8 73.5(4) . . . . ?
C21 C23 C41 C42 177.3(3) . . . . ?
C21 C23 C45 C50 -178.2(3) . . . . ?
C21 C30 C36 C16 0.8(5) . . . . ?
C21 C30 C36 N3 176.0(3) . . . . ?
C22 C24 C30 C21 9.1(5) . . . . ?
C22 C24 C30 C36 -173.2(3) . . . . ?
C22 C24 C44 N1 174.0(3) . . . . ?
C22 C24 C44 C43 -5.2(5) . . . . ?
C23 C21 C30 C24 -113.4(4) . . . . ?
C23 C21 C30 C36 69.0(4) . . . . ?
C23 C41 C42 C53 1.1(5) . . . . ?
C23 C45 C50 C53 0.6(6) . . . . ?
C24 C30 C36 C16 -177.0(3) . . . . ?
C24 C30 C36 N3 -1.7(5) . . . . ?
N3 N1 C44 C24 -0.5(5) . . . . ?
N3 N1 C44 C43 178.9(3) . . . . ?
C27 N2 N4 C19 -1.8(5) . . . . ?
C27 C20 C55 F1 146.6(3) . . . . ?
C27 C20 C55 F2 27.2(4) . . . . ?
C27 C20 C55 F3 -93.3(4) . . . . ?
C28 C15 C17 C19 -68.1(4) . . . . ?
C28 C15 C17 C20 116.2(4) . . . . ?
C28 C32 C34 C49 -0.8(5) . . . . ?
C28 C47 C51 C49 -1.8(5) . . . . ?
C29 O8 C33 C1 115.1(4) . . . . ?
C30 C21 C23 C41 13.8(5) . . . . ?
C30 C21 C23 C45 -168.0(3) . . . . ?
C30 C24 C44 N1 -2.8(5) . . . . ?
C30 C24 C44 C43 177.9(3) . . . . ?
C31 C37 C38 O1 -13.8(5) . . . . ?
C31 C37 C38 C19 166.9(3) . . . . ?
C31 C52 C60 C46 1.2(7) . . . . ?
C32 C28 C47 C51 1.1(5) . . . . ?
C32 C34 C49 C51 0.1(5) . . . . ?
C33 O8 C29 O3 4.5(6) . . . . ?
C33 O8 C29 C27 -177.9(3) . . . . ?
C34 C49 C51 C47 1.2(5) . . . . ?
C35 C37 C38 O1 164.8(4) . . . . ?
C35 C37 C38 C19 -14.5(5) . . . . ?
C35 C46 C60 C52 1.0(7) . . . . ?
C36 C16 C39 C57 15.3(5) . . . . ?
C36 C16 C39 C61 -166.2(3) . . . . ?
C37 C31 C52 C60 -2.3(6) . . . . ?
C37 C35 C46 C60 -2.2(6) . . . . ?
C39 C16 C36 N3 45.1(4) . . . . ?
C39 C16 C36 C30 -139.3(3) . . . . ?
C39 C57 C58 C54 0.0(6) . . . . ?
C41 C23 C45 C50 0.0(5) . . . . ?
C41 C42 C53 C50 -0.5(6) . . . . ?
C43 O7 C48 C2 -161.7(4) . . . . ?
C44 N1 N3 C36 2.6(4) . . . . ?
C44 C24 C30 C21 -174.0(3) . . . . ?
C44 C24 C30 C36 3.7(4) . . . . ?
C45 C23 C41 C42 -0.8(5) . . . . ?
C45 C50 C53 C42 -0.3(6) . . . . ?
C46 C35 C37 C31 1.1(6) . . . . ?
C46 C35 C37 C38 -177.5(4) . . . . ?
C47 C28 C32 C34 0.2(5) . . . . ?
C48 O7 C43 O5 -3.6(5) . . . . ?
C48 O7 C43 C44 177.5(3) . . . . ?
C52 C31 C37 C35 1.2(6) . . . . ?
C52 C31 C37 C38 179.8(4) . . . . ?
C54 C56 C61 C39 1.4(6) . . . . ?
C55 C20 C27 N2 -176.5(3) . . . . ?
C55 C20 C27 C29 2.8(5) . . . . ?
C56 C54 C58 C57 0.7(7) . . . . ?
C57 C39 C61 C56 -0.6(6) . . . . ?
C58 C54 C56 C61 -1.4(7) . . . . ?
C61 C39 C57 C58 0.0(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
