# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_mo_d8v21842_0m
_audit_block_doi                 10.5517/ccdc.csd.cc29wy8f
_database_code_depnum_ccdc_archive 'CCDC 2142015'
loop_
_audit_author_name
_audit_author_address
'chaolai tong'
;Shanghai institute of Organic Chemistry,Chinese Academy of Sciences
China
;
_audit_update_record             
;
2022-01-14 deposited with the CCDC.	2022-07-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H8 F7 N O'
_chemical_formula_weight         339.21

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.1368(5)
_cell_length_b                   7.7148(3)
_cell_length_c                   15.2040(6)
_cell_angle_alpha                90
_cell_angle_beta                 111.4880(10)
_cell_angle_gamma                90
_cell_volume                     1433.79(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6818
_cell_measurement_theta_min      5.497
_cell_measurement_theta_max      50.164

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.161
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5292
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20585
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_av_R_equivalents  0.0665
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.748
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2799
_reflns_number_gt                1988
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1169P)²+0.5253P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.056(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2799
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0703
_refine_ls_wR_factor_ref         0.2310
_refine_ls_wR_factor_gt          0.2044
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

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 0.77615(18) 0.4000(4) 0.49158(15) 0.1220(9) Uani 1 1 d . . . . .
F2 F 0.7618(3) 0.0517(5) 0.4966(2) 0.1786(14) Uani 1 1 d . . . . .
F3 F 0.9137(3) 0.0390(5) 0.6099(2) 0.1774(15) Uani 1 1 d . . . . .
F4 F 0.9050(3) 0.1517(6) 0.4802(2) 0.1903(17) Uani 1 1 d . . . . .
F5 F 0.9910(2) 0.3388(6) 0.7073(2) 0.1721(16) Uani 1 1 d . . . . .
F6 F 0.9983(2) 0.4313(7) 0.5803(2) 0.2017(19) Uani 1 1 d . . . . .
F7 F 0.9051(4) 0.5707(6) 0.6453(4) 0.218(2) Uani 1 1 d . . . . .
O1 O 0.43754(15) 0.4123(3) 0.56262(13) 0.0861(7) Uani 1 1 d . . . . .
N1 N 0.65539(16) 0.3540(3) 0.59837(14) 0.0636(6) Uani 1 1 d . . . . .
H1 H 0.6237 0.4060 0.5453 0.076 Uiso 1 1 calc R U . . .
C1 C 0.7593(2) 0.2941(4) 0.63056(19) 0.0697(7) Uani 1 1 d . . . . .
C2 C 0.7796(2) 0.2179(4) 0.7172(2) 0.0808(9) Uani 1 1 d . . . . .
H2 H 0.8448 0.1658 0.7551 0.097 Uiso 1 1 calc R U . . .
C3 C 0.6856(2) 0.2326(4) 0.7379(2) 0.0734(8) Uani 1 1 d . . . . .
H3 H 0.6761 0.1919 0.7920 0.088 Uiso 1 1 calc R U . . .
C4 C 0.6082(2) 0.3193(3) 0.66313(17) 0.0609(7) Uani 1 1 d . . . . .
C5 C 0.4943(2) 0.3612(3) 0.64206(17) 0.0636(7) Uani 1 1 d . . . . .
C6 C 0.4455(2) 0.3347(3) 0.71491(19) 0.0657(7) Uani 1 1 d . . . . .
C7 C 0.5021(3) 0.3658(4) 0.81074(19) 0.0773(8) Uani 1 1 d . . . . .
H7 H 0.5744 0.4035 0.8317 0.093 Uiso 1 1 calc R U . . .
C8 C 0.4512(4) 0.3406(5) 0.8745(3) 0.0977(11) Uani 1 1 d . . . . .
H8 H 0.4895 0.3629 0.9382 0.117 Uiso 1 1 calc R U . . .
C9 C 0.3474(4) 0.2846(5) 0.8462(3) 0.1082(13) Uani 1 1 d . . . . .
H9 H 0.3149 0.2667 0.8905 0.130 Uiso 1 1 calc R U . . .
C10 C 0.2880(3) 0.2532(5) 0.7508(4) 0.1041(12) Uani 1 1 d . . . . .
H10 H 0.2162 0.2141 0.7312 0.125 Uiso 1 1 calc R U . . .
C11 C 0.3373(3) 0.2810(4) 0.6854(3) 0.0815(9) Uani 1 1 d . . . . .
H11 H 0.2976 0.2635 0.6215 0.098 Uiso 1 1 calc R U . . .
C12 C 0.8299(2) 0.3118(5) 0.5731(2) 0.0846(9) Uani 1 1 d . . . . .
C13 C 0.8538(4) 0.1349(8) 0.5402(3) 0.1235(16) Uani 1 1 d . . . . .
C14 C 0.9348(4) 0.4187(9) 0.6274(4) 0.1273(16) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C12 1.362(3) . ?
F2 C13 1.313(6) . ?
F3 C13 1.296(5) . ?
F4 C13 1.324(5) . ?
F5 C14 1.320(6) . ?
F6 C14 1.287(5) . ?
F7 C14 1.296(7) . ?
O1 C5 1.229(3) . ?
N1 C1 1.352(3) . ?
N1 C4 1.368(3) . ?
N1 H1 0.8600 . ?
C1 C2 1.377(4) . ?
C1 C12 1.495(4) . ?
C2 C3 1.387(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.447(4) . ?
C5 C6 1.484(4) . ?
C6 C11 1.388(4) . ?
C6 C7 1.393(4) . ?
C7 C8 1.378(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.342(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.394(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.387(5) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.526(6) . ?
C12 C14 1.558(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C4 109.6(2) . . ?
C1 N1 H1 125.2 . . ?
C4 N1 H1 125.2 . . ?
N1 C1 C2 108.0(3) . . ?
N1 C1 C12 121.1(2) . . ?
C2 C1 C12 130.8(3) . . ?
C1 C2 C3 107.8(2) . . ?
C1 C2 H2 126.1 . . ?
C3 C2 H2 126.1 . . ?
C2 C3 C4 107.4(3) . . ?
C2 C3 H3 126.3 . . ?
C4 C3 H3 126.3 . . ?
N1 C4 C3 107.2(2) . . ?
N1 C4 C5 120.1(2) . . ?
C3 C4 C5 132.5(3) . . ?
O1 C5 C4 119.7(2) . . ?
O1 C5 C6 120.3(2) . . ?
C4 C5 C6 119.9(2) . . ?
C11 C6 C7 118.7(3) . . ?
C11 C6 C5 118.2(3) . . ?
C7 C6 C5 123.1(3) . . ?
C8 C7 C6 120.0(3) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C9 C8 C7 121.2(4) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 120.3(4) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 119.3(4) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C6 120.4(3) . . ?
C10 C11 H11 119.8 . . ?
C6 C11 H11 119.8 . . ?
F1 C12 C1 110.6(2) . . ?
F1 C12 C13 104.4(3) . . ?
C1 C12 C13 110.8(3) . . ?
F1 C12 C14 106.3(3) . . ?
C1 C12 C14 110.8(3) . . ?
C13 C12 C14 113.5(4) . . ?
F3 C13 F2 107.8(5) . . ?
F3 C13 F4 108.1(4) . . ?
F2 C13 F4 107.8(4) . . ?
F3 C13 C12 112.2(4) . . ?
F2 C13 C12 110.0(3) . . ?
F4 C13 C12 110.8(5) . . ?
F6 C14 F7 110.8(5) . . ?
F6 C14 F5 106.8(4) . . ?
F7 C14 F5 109.9(5) . . ?
F6 C14 C12 111.9(4) . . ?
F7 C14 C12 108.3(4) . . ?
F5 C14 C12 109.2(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
C4 N1 C1 C2 0.6(3) . . . . ?
C4 N1 C1 C12 179.0(3) . . . . ?
N1 C1 C2 C3 -0.2(3) . . . . ?
C12 C1 C2 C3 -178.3(3) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C1 N1 C4 C3 -0.7(3) . . . . ?
C1 N1 C4 C5 -176.1(2) . . . . ?
C2 C3 C4 N1 0.6(3) . . . . ?
C2 C3 C4 C5 175.1(3) . . . . ?
N1 C4 C5 O1 7.0(4) . . . . ?
C3 C4 C5 O1 -166.9(3) . . . . ?
N1 C4 C5 C6 -175.8(2) . . . . ?
C3 C4 C5 C6 10.3(4) . . . . ?
O1 C5 C6 C11 32.6(4) . . . . ?
C4 C5 C6 C11 -144.6(3) . . . . ?
O1 C5 C6 C7 -145.6(3) . . . . ?
C4 C5 C6 C7 37.2(4) . . . . ?
C11 C6 C7 C8 0.9(4) . . . . ?
C5 C6 C7 C8 179.1(3) . . . . ?
C6 C7 C8 C9 0.7(5) . . . . ?
C7 C8 C9 C10 -1.0(6) . . . . ?
C8 C9 C10 C11 -0.2(6) . . . . ?
C9 C10 C11 C6 1.8(5) . . . . ?
C7 C6 C11 C10 -2.2(4) . . . . ?
C5 C6 C11 C10 179.5(3) . . . . ?
N1 C1 C12 F1 2.9(4) . . . . ?
C2 C1 C12 F1 -179.1(3) . . . . ?
N1 C1 C12 C13 -112.4(3) . . . . ?
C2 C1 C12 C13 65.6(4) . . . . ?
N1 C1 C12 C14 120.6(4) . . . . ?
C2 C1 C12 C14 -61.4(5) . . . . ?
F1 C12 C13 F3 174.3(4) . . . . ?
C1 C12 C13 F3 -66.6(5) . . . . ?
C14 C12 C13 F3 59.0(6) . . . . ?
F1 C12 C13 F2 -65.7(5) . . . . ?
C1 C12 C13 F2 53.4(4) . . . . ?
C14 C12 C13 F2 178.9(4) . . . . ?
F1 C12 C13 F4 53.4(4) . . . . ?
C1 C12 C13 F4 172.5(3) . . . . ?
C14 C12 C13 F4 -62.0(5) . . . . ?
F1 C12 C14 F6 -61.6(6) . . . . ?
C1 C12 C14 F6 178.1(4) . . . . ?
C13 C12 C14 F6 52.6(6) . . . . ?
F1 C12 C14 F7 60.8(5) . . . . ?
C1 C12 C14 F7 -59.5(5) . . . . ?
C13 C12 C14 F7 175.0(4) . . . . ?
F1 C12 C14 F5 -179.6(4) . . . . ?
C1 C12 C14 F5 60.1(5) . . . . ?
C13 C12 C14 F5 -65.4(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.86 2.08 2.923(3) 165.4 3_666

_refine_diff_density_max         0.329
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.044

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_mo_d8v21856_0m
_database_code_depnum_ccdc_archive 'CCDC 2142019'
loop_
_audit_author_name
_audit_author_address
'chaolai tong'
;Shanghai institute of Organic Chemistry,Chinese Academy of Sciences
China
;
_audit_update_record             
;
2022-01-14 deposited with the CCDC.	2022-07-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H5 F7 N2 O2'
_chemical_formula_weight         330.17

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.8411(4)
_cell_length_b                   7.4893(6)
_cell_length_c                   15.3251(11)
_cell_angle_alpha                93.549(2)
_cell_angle_beta                 99.686(2)
_cell_angle_gamma                103.603(2)
_cell_volume                     638.70(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3876
_cell_measurement_theta_min      5.424
_cell_measurement_theta_max      53.241

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.186
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6369
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8513
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.712
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             2226
_reflns_number_gt                1737
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1509P)²+0.3656P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2226
_refine_ls_number_parameters     199
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0803
_refine_ls_wR_factor_ref         0.2593
_refine_ls_wR_factor_gt          0.2404
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

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 0.9212(5) 0.6376(7) 0.3049(2) 0.1467(16) Uani 1 1 d . . . . .
F2 F 0.3991(8) 0.4284(8) 0.3744(3) 0.1724(19) Uani 1 1 d . U . . .
F3 F 0.6375(7) 0.3187(4) 0.3051(3) 0.1371(14) Uani 1 1 d . . . . .
F4 F 0.7707(9) 0.4487(5) 0.4367(2) 0.1606(18) Uani 1 1 d . . . . .
F5 F 0.5188(12) 0.8012(8) 0.4185(3) 0.179(2) Uani 1 1 d . U . . .
F6 F 0.7889(10) 0.9543(5) 0.3576(3) 0.188(2) Uani 1 1 d . . . . .
F7 F 0.8855(10) 0.7993(5) 0.4625(3) 0.193(3) Uani 1 1 d . . . . .
O1 O -0.3744(5) 1.1710(4) 0.08519(19) 0.0820(9) Uani 1 1 d . . . . .
O2 O 0.3908(4) 0.7684(3) 0.23626(16) 0.0660(7) Uani 1 1 d . . . . .
N1 N -0.2325(5) 0.9233(4) 0.05496(19) 0.0612(8) Uani 1 1 d . . . . .
H1 H -0.3483 0.8903 0.0099 0.073 Uiso 1 1 calc R U . . .
N2 N -0.0839(5) 0.8102(4) 0.06879(18) 0.0594(7) Uani 1 1 d . . . . .
C1 C -0.2191(6) 1.0844(5) 0.1047(2) 0.0648(9) Uani 1 1 d . . . . .
C2 C -0.0205(7) 1.1370(6) 0.1765(3) 0.0811(12) Uani 1 1 d . . . . .
H2 H 0.0062 1.2478 0.2120 0.097 Uiso 1 1 calc R U . . .
C3 C 0.1291(7) 1.0261(5) 0.1929(3) 0.0762(11) Uani 1 1 d . . . . .
H3 H 0.2561 1.0578 0.2412 0.091 Uiso 1 1 calc R U . . .
C4 C 0.0923(5) 0.8617(4) 0.1367(2) 0.0574(8) Uani 1 1 d . . . . .
C5 C 0.2520(6) 0.7380(5) 0.1537(2) 0.0587(8) Uani 1 1 d . . . . .
C6 C 0.2973(6) 0.5983(5) 0.1059(2) 0.0682(9) Uani 1 1 d . . . . .
H6 H 0.2265 0.5517 0.0474 0.082 Uiso 1 1 calc R U . . .
C7 C 0.4742(7) 0.5359(5) 0.1621(3) 0.0718(10) Uani 1 1 d . . . . .
H7 H 0.5423 0.4402 0.1477 0.086 Uiso 1 1 calc R U . . .
C8 C 0.5241(6) 0.6396(5) 0.2391(3) 0.0663(9) Uani 1 1 d . . . . .
C9 C 0.6886(7) 0.6396(6) 0.3243(3) 0.0806(11) Uani 1 1 d . . . . .
C10 C 0.6306(12) 0.4524(8) 0.3623(4) 0.1080(15) Uani 1 1 d . U . . .
C11 C 0.7288(14) 0.8018(8) 0.3909(4) 0.1247(18) Uani 1 1 d . 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 C9 1.442(5) . ?
F2 C10 1.367(8) . ?
F3 C10 1.301(6) . ?
F4 C10 1.293(6) . ?
F5 C11 1.362(9) . ?
F6 C11 1.278(7) . ?
F7 C11 1.310(6) . ?
O1 C1 1.242(4) . ?
O2 C5 1.357(4) . ?
O2 C8 1.374(4) . ?
N1 N2 1.350(3) . ?
N1 C1 1.365(5) . ?
N1 H1 0.8600 . ?
N2 C4 1.302(4) . ?
C1 C2 1.418(5) . ?
C2 C3 1.345(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.409(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.467(4) . ?
C5 C6 1.342(5) . ?
C6 C7 1.417(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.320(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.485(5) . ?
C9 C11 1.484(7) . ?
C9 C10 1.537(7) . ?

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
C5 O2 C8 105.9(3) . . ?
N2 N1 C1 127.2(3) . . ?
N2 N1 H1 116.4 . . ?
C1 N1 H1 116.4 . . ?
C4 N2 N1 116.1(3) . . ?
O1 C1 N1 119.7(3) . . ?
O1 C1 C2 125.7(3) . . ?
N1 C1 C2 114.5(3) . . ?
C3 C2 C1 119.8(4) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
N2 C4 C3 122.6(3) . . ?
N2 C4 C5 116.7(3) . . ?
C3 C4 C5 120.7(3) . . ?
C6 C5 O2 110.3(3) . . ?
C6 C5 C4 134.9(3) . . ?
O2 C5 C4 114.8(3) . . ?
C5 C6 C7 106.4(3) . . ?
C5 C6 H6 126.8 . . ?
C7 C6 H6 126.8 . . ?
C8 C7 C6 106.9(3) . . ?
C8 C7 H7 126.6 . . ?
C6 C7 H7 126.6 . . ?
C7 C8 O2 110.5(3) . . ?
C7 C8 C9 132.6(3) . . ?
O2 C8 C9 116.9(3) . . ?
F1 C9 C8 108.2(4) . . ?
F1 C9 C11 106.0(5) . . ?
C8 C9 C11 116.1(4) . . ?
F1 C9 C10 98.8(4) . . ?
C8 C9 C10 111.7(4) . . ?
C11 C9 C10 114.2(5) . . ?
F4 C10 F3 109.6(5) . . ?
F4 C10 F2 110.4(5) . . ?
F3 C10 F2 108.1(5) . . ?
F4 C10 C9 113.0(5) . . ?
F3 C10 C9 111.1(5) . . ?
F2 C10 C9 104.4(4) . . ?
F6 C11 F7 109.9(6) . . ?
F6 C11 F5 106.1(6) . . ?
F7 C11 F5 106.3(6) . . ?
F6 C11 C9 112.1(6) . . ?
F7 C11 C9 113.3(5) . . ?
F5 C11 C9 108.8(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
C1 N1 N2 C4 -0.6(5) . . . . ?
N2 N1 C1 O1 -177.7(3) . . . . ?
N2 N1 C1 C2 2.2(5) . . . . ?
O1 C1 C2 C3 176.9(4) . . . . ?
N1 C1 C2 C3 -3.0(6) . . . . ?
C1 C2 C3 C4 2.3(7) . . . . ?
N1 N2 C4 C3 -0.3(5) . . . . ?
N1 N2 C4 C5 178.7(3) . . . . ?
C2 C3 C4 N2 -0.6(6) . . . . ?
C2 C3 C4 C5 -179.6(4) . . . . ?
C8 O2 C5 C6 -0.8(4) . . . . ?
C8 O2 C5 C4 179.6(3) . . . . ?
N2 C4 C5 C6 17.4(6) . . . . ?
C3 C4 C5 C6 -163.6(4) . . . . ?
N2 C4 C5 O2 -163.2(3) . . . . ?
C3 C4 C5 O2 15.9(5) . . . . ?
O2 C5 C6 C7 0.5(4) . . . . ?
C4 C5 C6 C7 180.0(4) . . . . ?
C5 C6 C7 C8 0.0(4) . . . . ?
C6 C7 C8 O2 -0.5(4) . . . . ?
C6 C7 C8 C9 178.5(4) . . . . ?
C5 O2 C8 C7 0.8(4) . . . . ?
C5 O2 C8 C9 -178.4(3) . . . . ?
C7 C8 C9 F1 50.0(6) . . . . ?
O2 C8 C9 F1 -131.1(4) . . . . ?
C7 C8 C9 C11 168.9(6) . . . . ?
O2 C8 C9 C11 -12.2(6) . . . . ?
C7 C8 C9 C10 -57.8(7) . . . . ?
O2 C8 C9 C10 121.2(4) . . . . ?
F1 C9 C10 F4 66.5(6) . . . . ?
C8 C9 C10 F4 -179.8(5) . . . . ?
C11 C9 C10 F4 -45.6(7) . . . . ?
F1 C9 C10 F3 -57.2(5) . . . . ?
C8 C9 C10 F3 56.6(6) . . . . ?
C11 C9 C10 F3 -169.2(5) . . . . ?
F1 C9 C10 F2 -173.5(4) . . . . ?
C8 C9 C10 F2 -59.8(5) . . . . ?
C11 C9 C10 F2 74.5(6) . . . . ?
F1 C9 C11 F6 68.8(6) . . . . ?
C8 C9 C11 F6 -51.3(8) . . . . ?
C10 C9 C11 F6 176.5(5) . . . . ?
F1 C9 C11 F7 -56.2(7) . . . . ?
C8 C9 C11 F7 -176.4(5) . . . . ?
C10 C9 C11 F7 51.4(8) . . . . ?
F1 C9 C11 F5 -174.2(4) . . . . ?
C8 C9 C11 F5 65.7(6) . . . . ?
C10 C9 C11 F5 -66.5(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7 O1 0.93 2.37 3.275(4) 165.9 1_645
C3 H3 F3 0.93 2.59 3.366(5) 141.0 1_565
N1 H1 O1 0.86 1.93 2.788(4) 174.5 2_475
C7 H7 O1 0.93 2.37 3.275(4) 165.9 1_645
C3 H3 F3 0.93 2.59 3.366(5) 141.0 1_565
N1 H1 O1 0.86 1.93 2.788(4) 174.5 2_475
C7 H7 O1 0.93 2.37 3.275(4) 165.9 1_645
C3 H3 F3 0.93 2.59 3.366(5) 141.0 1_565
N1 H1 O1 0.86 1.93 2.788(4) 174.5 2_475
N1 H1 O1 0.86 1.93 2.788(4) 174.5 2_475
C3 H3 F3 0.93 2.59 3.366(5) 141.0 1_565
C7 H7 O1 0.93 2.37 3.275(4) 165.9 1_645
N1 H1 O1 0.86 1.93 2.788(4) 174.5 2_475
C3 H3 F3 0.93 2.59 3.366(5) 141.0 1_565
C7 H7 O1 0.93 2.37 3.275(4) 165.9 1_645
N1 H1 O1 0.86 1.93 2.788(4) 174.5 2_475
C3 H3 F3 0.93 2.59 3.366(5) 141.0 1_565
C7 H7 O1 0.93 2.37 3.275(4) 165.9 1_645
N1 H1 O1 0.86 1.93 2.788(4) 174.5 2_475
C3 H3 F3 0.93 2.59 3.366(5) 141.0 1_565
C7 H7 O1 0.93 2.37 3.275(4) 165.9 1_645

_refine_diff_density_max         0.523
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.059

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_mo_d8v21846_0m
_database_code_depnum_ccdc_archive 'CCDC 2142017'
loop_
_audit_author_name
_audit_author_address
'chaolai tong'
;Shanghai institute of Organic Chemistry,Chinese Academy of Sciences
China
;
_audit_update_record             
;
2022-01-14 deposited with the CCDC.	2022-07-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H5 F7 N2 O3'
_chemical_formula_weight         358.18

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.5625(6)
_cell_length_b                   6.7748(3)
_cell_length_c                   15.5762(6)
_cell_angle_alpha                90
_cell_angle_beta                 115.6730(10)
_cell_angle_gamma                90
_cell_volume                     1385.01(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7534
_cell_measurement_theta_min      5.264
_cell_measurement_theta_max      54.932

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.718
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.184
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5960
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18273
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.632
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.961
_reflns_number_total             2412
_reflns_number_gt                1934
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0666P)²+0.4655P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.041(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2412
_refine_ls_number_parameters     299
_refine_ls_number_restraints     137
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1436
_refine_ls_wR_factor_gt          0.1301
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.177
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.004

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.09908(18) 0.1255(4) 0.75968(18) 0.0765(7) Uani 1 1 d . . . . .
H1 H 0.0519 0.0610 0.7752 0.092 Uiso 1 1 calc R U . . .
C2 C 0.24014(16) 0.2089(3) 0.75917(15) 0.0659(6) Uani 1 1 d D . . . .
C3 C 0.16480(15) 0.3181(3) 0.69430(14) 0.0597(5) Uani 1 1 d . . . . .
C4 C 0.16449(15) 0.4739(3) 0.62851(13) 0.0586(5) Uani 1 1 d . . . . .
C5 C 0.10974(19) 0.6450(4) 0.62099(17) 0.0787(7) Uani 1 1 d . . . . .
H5 H 0.0754 0.6610 0.6588 0.094 Uiso 1 1 calc R U . . .
C6 C 0.1054(2) 0.7913(4) 0.55866(18) 0.0817(7) Uani 1 1 d . . . . .
H6 H 0.0698 0.9074 0.5550 0.098 Uiso 1 1 calc R U . . .
C7 C 0.15439(16) 0.7638(3) 0.50176(14) 0.0628(6) Uani 1 1 d . . . . .
C8 C 0.21013(19) 0.5979(4) 0.50776(16) 0.0728(6) Uani 1 1 d . . . . .
H8 H 0.2439 0.5830 0.4693 0.087 Uiso 1 1 calc R U . . .
C9 C 0.21544(19) 0.4532(3) 0.57170(16) 0.0718(6) Uani 1 1 d . . . . .
H9 H 0.2537 0.3400 0.5769 0.086 Uiso 1 1 calc R U . . .
C10 C 0.35316(19) 0.2059(4) 0.7982(2) 0.0887(7) Uani 1 1 d D U . . .
C11 C 0.3966(5) 0.0445(11) 0.7717(6) 0.0966(15) Uani 0.5 1 d D U P A 1
C12 C 0.4026(6) 0.2489(12) 0.9123(6) 0.0927(16) Uani 0.5 1 d D U P A 1
F1 F 0.3811(4) 0.3861(7) 0.7671(4) 0.0923(14) Uani 0.5 1 d . U P A 1
F2 F 0.3648(8) -0.1273(9) 0.7967(9) 0.187(4) Uani 0.6 1 d D U P A 1
F3 F 0.4960(5) 0.0466(11) 0.8082(7) 0.170(3) Uani 0.6 1 d D U P A 1
F4 F 0.3623(5) 0.0424(12) 0.6805(4) 0.174(2) Uani 0.6 1 d D U P A 1
F5 F 0.3968(4) 0.0833(12) 0.9520(5) 0.139(3) Uani 0.5 1 d D U P A 1
F6 F 0.3589(5) 0.3956(14) 0.9321(4) 0.139(2) Uani 0.5 1 d D U P A 1
F7 F 0.5000(9) 0.285(3) 0.9422(10) 0.128(3) Uani 0.5 1 d D U P A 1
C11' C 0.3903(6) -0.0307(15) 0.8063(7) 0.1006(17) Uani 0.5 1 d D U P A 2
C12' C 0.4087(7) 0.3045(13) 0.8893(6) 0.1024(19) Uani 0.5 1 d D U P A 2
F1' F 0.3821(5) 0.2738(15) 0.7333(5) 0.178(4) Uani 0.5 1 d . U P A 2
F2' F 0.3416(7) -0.118(2) 0.7258(8) 0.173(5) Uani 0.4 1 d D U P A 2
F3' F 0.4876(7) -0.0514(14) 0.8294(7) 0.131(3) Uani 0.4 1 d D U P A 2
F4' F 0.3811(5) -0.1147(12) 0.8796(7) 0.146(3) Uani 0.4 1 d D U P A 2
F5' F 0.5074(11) 0.304(4) 0.9170(12) 0.179(7) Uani 0.5 1 d D U P A 2
F6' F 0.3809(5) 0.4864(9) 0.8707(9) 0.238(5) Uani 0.5 1 d D U P A 2
F7' F 0.3811(7) 0.2321(19) 0.9524(5) 0.169(4) Uani 0.5 1 d D U P A 2
N1 N 0.07368(14) 0.2604(3) 0.69658(13) 0.0710(6) Uani 1 1 d . . . . .
N2 N 0.14574(16) 0.9146(3) 0.43124(14) 0.0770(6) Uani 1 1 d . . . . .
O1 O 0.19930(12) 0.0831(2) 0.80232(12) 0.0772(5) Uani 1 1 d . . . . .
O2 O 0.10971(18) 1.0739(3) 0.43568(15) 0.1045(7) Uani 1 1 d . . . . .
O3 O 0.17138(18) 0.8716(3) 0.36914(15) 0.1097(8) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.274(3) . ?
C1 O1 1.347(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.346(3) . ?
C2 O1 1.370(2) . ?
C2 C10 1.487(3) . ?
C3 N1 1.399(3) . ?
C3 C4 1.470(3) . ?
C4 C9 1.386(3) . ?
C4 C5 1.383(3) . ?
C5 C6 1.369(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.370(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.366(3) . ?
C7 N2 1.465(3) . ?
C8 C9 1.376(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 F1' 1.334(6) . ?
C10 C11 1.411(7) . ?
C10 F1 1.436(6) . ?
C10 C12' 1.456(9) . ?
C10 C12 1.629(10) . ?
C10 C11' 1.679(10) . ?
C11 F4 1.286(8) . ?
C11 F3 1.305(9) . ?
C11 F2 1.370(9) . ?
C12 F6 1.288(11) . ?
C12 F5 1.301(10) . ?
C12 F7 1.310(13) . ?
C11' F2' 1.287(11) . ?
C11' F3' 1.310(11) . ?
C11' F4' 1.334(12) . ?
C12' F6' 1.290(10) . ?
C12' F7' 1.309(10) . ?
C12' F5' 1.309(13) . ?
N2 O3 1.214(3) . ?
N2 O2 1.215(3) . ?

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
N1 C1 O1 115.07(19) . . ?
N1 C1 H1 122.5 . . ?
O1 C1 H1 122.5 . . ?
C3 C2 O1 108.92(18) . . ?
C3 C2 C10 135.4(2) . . ?
O1 C2 C10 115.46(18) . . ?
C2 C3 N1 107.50(18) . . ?
C2 C3 C4 132.34(19) . . ?
N1 C3 C4 120.16(18) . . ?
C9 C4 C5 118.6(2) . . ?
C9 C4 C3 122.09(19) . . ?
C5 C4 C3 119.25(18) . . ?
C6 C5 C4 121.0(2) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 118.9(2) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C8 C7 C6 121.9(2) . . ?
C8 C7 N2 118.73(19) . . ?
C6 C7 N2 119.4(2) . . ?
C7 C8 C9 118.8(2) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
C8 C9 C4 120.8(2) . . ?
C8 C9 H9 119.6 . . ?
C4 C9 H9 119.6 . . ?
C11 C10 F1 109.4(4) . . ?
F1' C10 C12' 110.8(6) . . ?
F1' C10 C2 110.0(3) . . ?
C11 C10 C2 116.6(4) . . ?
F1 C10 C2 106.0(3) . . ?
C12' C10 C2 116.2(4) . . ?
C11 C10 C12 114.5(5) . . ?
F1 C10 C12 99.2(4) . . ?
C2 C10 C12 109.3(3) . . ?
F1' C10 C11' 100.9(6) . . ?
C12' C10 C11' 109.9(5) . . ?
C2 C10 C11' 107.9(3) . . ?
F4 C11 F3 107.9(7) . . ?
F4 C11 F2 106.7(8) . . ?
F3 C11 F2 109.5(8) . . ?
F4 C11 C10 108.8(6) . . ?
F3 C11 C10 114.7(7) . . ?
F2 C11 C10 109.0(6) . . ?
F6 C12 F5 114.3(9) . . ?
F6 C12 F7 110.0(12) . . ?
F5 C12 F7 105.9(10) . . ?
F6 C12 C10 111.7(6) . . ?
F5 C12 C10 106.0(7) . . ?
F7 C12 C10 108.6(9) . . ?
F2' C11' F3' 107.0(9) . . ?
F2' C11' F4' 114.9(13) . . ?
F3' C11' F4' 102.5(8) . . ?
F2' C11' C10 110.0(9) . . ?
F3' C11' C10 113.4(8) . . ?
F4' C11' C10 108.8(6) . . ?
F6' C12' F7' 110.9(11) . . ?
F6' C12' F5' 105.8(13) . . ?
F7' C12' F5' 113.7(10) . . ?
F6' C12' C10 103.4(8) . . ?
F7' C12' C10 109.8(7) . . ?
F5' C12' C10 112.7(12) . . ?
C1 N1 C3 105.00(19) . . ?
O3 N2 O2 123.2(2) . . ?
O3 N2 C7 118.3(2) . . ?
O2 N2 C7 118.4(2) . . ?
C1 O1 C2 103.51(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 N1 0.2(2) . . . . ?
C10 C2 C3 N1 -173.9(3) . . . . ?
O1 C2 C3 C4 179.9(2) . . . . ?
C10 C2 C3 C4 5.8(5) . . . . ?
C2 C3 C4 C9 47.6(4) . . . . ?
N1 C3 C4 C9 -132.7(2) . . . . ?
C2 C3 C4 C5 -134.0(3) . . . . ?
N1 C3 C4 C5 45.7(3) . . . . ?
C9 C4 C5 C6 0.2(4) . . . . ?
C3 C4 C5 C6 -178.3(2) . . . . ?
C4 C5 C6 C7 1.5(4) . . . . ?
C5 C6 C7 C8 -2.3(4) . . . . ?
C5 C6 C7 N2 176.7(2) . . . . ?
C6 C7 C8 C9 1.2(4) . . . . ?
N2 C7 C8 C9 -177.8(2) . . . . ?
C7 C8 C9 C4 0.6(4) . . . . ?
C5 C4 C9 C8 -1.3(4) . . . . ?
C3 C4 C9 C8 177.1(2) . . . . ?
C3 C2 C10 F1' -28.4(7) . . . . ?
O1 C2 C10 F1' 157.8(6) . . . . ?
C3 C2 C10 C11 -109.6(5) . . . . ?
O1 C2 C10 C11 76.7(5) . . . . ?
C3 C2 C10 F1 12.4(5) . . . . ?
O1 C2 C10 F1 -161.3(3) . . . . ?
C3 C2 C10 C12' 98.5(5) . . . . ?
O1 C2 C10 C12' -75.3(5) . . . . ?
C3 C2 C10 C12 118.5(4) . . . . ?
O1 C2 C10 C12 -55.2(4) . . . . ?
C3 C2 C10 C11' -137.7(4) . . . . ?
O1 C2 C10 C11' 48.6(4) . . . . ?
F1' C10 C11 F4 -44.9(6) . . . . ?
F1 C10 C11 F4 -60.5(7) . . . . ?
C12' C10 C11 F4 -149.7(7) . . . . ?
C2 C10 C11 F4 59.7(7) . . . . ?
C12 C10 C11 F4 -170.8(6) . . . . ?
C11' C10 C11 F4 136.9(13) . . . . ?
F1' C10 C11 F3 76.1(7) . . . . ?
F1 C10 C11 F3 60.4(8) . . . . ?
C12' C10 C11 F3 -28.8(9) . . . . ?
C2 C10 C11 F3 -179.4(6) . . . . ?
C12 C10 C11 F3 -49.9(8) . . . . ?
C11' C10 C11 F3 -102.2(13) . . . . ?
F1' C10 C11 F2 -160.9(9) . . . . ?
F1 C10 C11 F2 -176.5(8) . . . . ?
C12' C10 C11 F2 94.3(9) . . . . ?
C2 C10 C11 F2 -56.3(9) . . . . ?
C12 C10 C11 F2 73.2(9) . . . . ?
C11' C10 C11 F2 20.9(10) . . . . ?
F1' C10 C12 F6 92.7(9) . . . . ?
C11 C10 C12 F6 -179.1(7) . . . . ?
F1 C10 C12 F6 64.6(8) . . . . ?
C12' C10 C12 F6 68.1(17) . . . . ?
C2 C10 C12 F6 -46.0(8) . . . . ?
C11' C10 C12 F6 -157.6(8) . . . . ?
F1' C10 C12 F5 -142.3(7) . . . . ?
C11 C10 C12 F5 -54.0(7) . . . . ?
F1 C10 C12 F5 -170.3(6) . . . . ?
C12' C10 C12 F5 -167(2) . . . . ?
C2 C10 C12 F5 79.0(6) . . . . ?
C11' C10 C12 F5 -32.6(7) . . . . ?
F1' C10 C12 F7 -28.8(13) . . . . ?
C11 C10 C12 F7 59.4(11) . . . . ?
F1 C10 C12 F7 -56.9(11) . . . . ?
C12' C10 C12 F7 -53.4(18) . . . . ?
C2 C10 C12 F7 -167.6(10) . . . . ?
C11' C10 C12 F7 80.9(11) . . . . ?
F1' C10 C11' F2' -62.7(10) . . . . ?
C11 C10 C11' F2' -61.0(11) . . . . ?
F1 C10 C11' F2' -84.5(11) . . . . ?
C12' C10 C11' F2' -179.7(10) . . . . ?
C2 C10 C11' F2' 52.7(10) . . . . ?
C12 C10 C11' F2' 165.4(10) . . . . ?
F1' C10 C11' F3' 57.1(9) . . . . ?
C11 C10 C11' F3' 58.9(11) . . . . ?
F1 C10 C11' F3' 35.3(11) . . . . ?
C12' C10 C11' F3' -59.9(9) . . . . ?
C2 C10 C11' F3' 172.5(7) . . . . ?
C12 C10 C11' F3' -74.8(8) . . . . ?
F1' C10 C11' F4' 170.5(6) . . . . ?
C11 C10 C11' F4' 172.3(14) . . . . ?
F1 C10 C11' F4' 148.7(6) . . . . ?
C12' C10 C11' F4' 53.5(8) . . . . ?
C2 C10 C11' F4' -74.1(6) . . . . ?
C12 C10 C11' F4' 38.7(7) . . . . ?
F1' C10 C12' F6' 63.2(9) . . . . ?
C11 C10 C12' F6' 145.9(8) . . . . ?
F1 C10 C12' F6' 39.5(8) . . . . ?
C2 C10 C12' F6' -63.4(9) . . . . ?
C12 C10 C12' F6' -137(2) . . . . ?
C11' C10 C12' F6' 173.8(8) . . . . ?
F1' C10 C12' F7' -178.4(9) . . . . ?
C11 C10 C12' F7' -95.7(10) . . . . ?
F1 C10 C12' F7' 157.9(9) . . . . ?
C2 C10 C12' F7' 55.1(10) . . . . ?
C12 C10 C12' F7' -18.6(14) . . . . ?
C11' C10 C12' F7' -67.7(10) . . . . ?
F1' C10 C12' F5' -50.6(12) . . . . ?
C11 C10 C12' F5' 32.1(13) . . . . ?
F1 C10 C12' F5' -74.3(11) . . . . ?
C2 C10 C12' F5' -177.1(11) . . . . ?
C12 C10 C12' F5' 109(2) . . . . ?
C11' C10 C12' F5' 60.1(12) . . . . ?
O1 C1 N1 C3 0.2(3) . . . . ?
C2 C3 N1 C1 -0.2(2) . . . . ?
C4 C3 N1 C1 -180.0(2) . . . . ?
C8 C7 N2 O3 13.8(3) . . . . ?
C6 C7 N2 O3 -165.2(2) . . . . ?
C8 C7 N2 O2 -168.9(2) . . . . ?
C6 C7 N2 O2 12.0(3) . . . . ?
N1 C1 O1 C2 -0.1(3) . . . . ?
C3 C2 O1 C1 0.0(3) . . . . ?
C10 C2 O1 C1 175.3(2) . . . . ?

_refine_diff_density_max         0.221
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.029

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_d8v21845
_database_code_depnum_ccdc_archive 'CCDC 2142020'
loop_
_audit_author_name
_audit_author_address
'chaolai tong'
;Shanghai institute of Organic Chemistry,Chinese Academy of Sciences
China
;
_audit_update_record             
;
2022-01-14 deposited with the CCDC.	2022-07-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H6 F7 N O4'
_chemical_formula_weight         361.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0659(7)
_cell_length_b                   11.0627(11)
_cell_length_c                   18.7151(18)
_cell_angle_alpha                94.470(3)
_cell_angle_beta                 99.704(3)
_cell_angle_gamma                90.033(3)
_cell_volume                     1437.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6398
_cell_measurement_theta_min      6.908
_cell_measurement_theta_max      50.511

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.181
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4198
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18644
_diffrn_reflns_av_unetI/netI     0.0582
_diffrn_reflns_av_R_equivalents  0.0631
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.847
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             5053
_reflns_number_gt                3091
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5053
_refine_ls_number_parameters     597
_refine_ls_number_restraints     280
_refine_ls_R_factor_all          0.1425
_refine_ls_R_factor_gt           0.1077
_refine_ls_wR_factor_ref         0.3479
_refine_ls_wR_factor_gt          0.2993
_refine_ls_goodness_of_fit_ref   1.250
_refine_ls_restrained_S_all      1.369
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7346(5) 0.9381(3) 0.4920(2) 0.0712(10) Uani 1 1 d . . . . .
C2 C 0.7975(5) 0.8545(3) 0.5438(2) 0.0708(10) Uani 1 1 d . . . . .
H2 H 0.7841 0.7704 0.5383 0.085 Uiso 1 1 calc R U . . .
C3 C 0.8818(6) 0.9241(3) 0.6032(2) 0.0713(10) Uani 1 1 d . . . . .
C4 C 0.9714(6) 0.9010(4) 0.6745(2) 0.0752(11) Uani 1 1 d . . . . .
C5 C 1.0255(6) 0.7973(4) 0.7080(2) 0.0842(12) Uani 1 1 d . . . . .
H5 H 1.0135 0.7186 0.6862 0.101 Uiso 1 1 calc R U . . .
C6 C 1.1012(7) 0.8308(5) 0.7802(3) 0.0989(14) Uani 1 1 d . . . . .
H6 H 1.1471 0.7797 0.8162 0.119 Uiso 1 1 calc R U . . .
C7 C 1.0943(7) 0.9539(5) 0.7871(3) 0.0959(14) Uani 1 1 d D . . . .
C8 C 0.6312(6) 0.9177(4) 0.4183(2) 0.0762(11) Uani 1 1 d . . . . .
C9 C 0.4664(7) 0.7757(5) 0.3300(3) 0.0968(14) Uani 1 1 d . . . . .
H9A H 0.3430 0.8131 0.3271 0.145 Uiso 1 1 calc R U . . .
H9B H 0.4496 0.6895 0.3209 0.145 Uiso 1 1 calc R U . . .
H9C H 0.5332 0.8061 0.2944 0.145 Uiso 1 1 calc R U . . .
C10 C 1.1470(10) 1.0495(7) 0.8487(4) 0.149(2) Uani 1 1 d D U . . .
C13 C 0.2319(5) 0.5599(3) 0.4900(2) 0.0705(10) Uani 1 1 d . . . . .
C14 C 0.2935(5) 0.6578(3) 0.5416(2) 0.0721(10) Uani 1 1 d . . . . .
H14 H 0.2791 0.7402 0.5360 0.086 Uiso 1 1 calc R U . . .
C15 C 0.3784(6) 0.6041(3) 0.6011(2) 0.0725(10) Uani 1 1 d . . . . .
C16 C 0.4702(6) 0.6464(3) 0.6729(2) 0.0731(10) Uani 1 1 d . . . . .
C17 C 0.5214(6) 0.7584(4) 0.7054(3) 0.0887(13) Uani 1 1 d . . . . .
H17 H 0.5063 0.8312 0.6834 0.106 Uiso 1 1 calc R U . . .
C18 C 0.6006(7) 0.7445(5) 0.7775(3) 0.0970(14) Uani 1 1 d . . . . .
H18 H 0.6486 0.8055 0.8130 0.116 Uiso 1 1 calc R U . . .
C19 C 0.5934(8) 0.6235(5) 0.7855(3) 0.1012(15) Uani 1 1 d D . . . .
C20 C 0.1275(6) 0.5599(4) 0.4152(2) 0.0768(11) Uani 1 1 d . . . . .
C21 C -0.0357(7) 0.6794(5) 0.3272(3) 0.1027(15) Uani 1 1 d . . . . .
H21A H 0.0401 0.6522 0.2912 0.154 Uiso 1 1 calc R U . . .
H21B H -0.0707 0.7623 0.3213 0.154 Uiso 1 1 calc R U . . .
H21C H -0.1498 0.6299 0.3214 0.154 Uiso 1 1 calc R U . . .
C22 C 0.6494(11) 0.5484(7) 0.8460(3) 0.154(2) Uani 1 1 d D U . . .
C11 C 1.303(2) 1.0197(14) 0.9104(8) 0.153(3) Uani 0.5 1 d D U P A 1
C12 C 0.977(2) 1.1204(16) 0.8671(9) 0.150(3) Uani 0.5 1 d D U P A 1
C23 C 0.462(2) 0.4987(16) 0.8746(9) 0.152(3) Uani 0.5 1 d D U P B 1
C24 C 0.860(3) 0.5733(15) 0.8863(8) 0.160(3) Uani 0.5 1 d D U P B 1
F1 F 1.291(2) 1.1408(14) 0.8251(10) 0.180(6) Uani 0.5 1 d D U P A 1
F2 F 1.4571(11) 0.9693(12) 0.8811(5) 0.150(4) Uani 0.5 1 d D U P A 1
F3 F 1.390(2) 1.1438(13) 0.9267(9) 0.199(6) Uani 0.5 1 d D U P A 1
F4 F 1.1978(19) 0.9310(12) 0.9339(5) 0.159(4) Uani 0.5 1 d D U P A 1
F5 F 1.018(2) 1.1802(12) 0.9339(6) 0.172(5) Uani 0.5 1 d D U P A 1
F6 F 0.844(2) 1.0408(16) 0.8762(11) 0.203(7) Uani 0.5 1 d D U P A 1
F7 F 0.944(3) 1.1899(17) 0.8115(10) 0.244(8) Uani 0.5 1 d D U P A 1
F8 F 0.6966(19) 0.4123(9) 0.8105(5) 0.141(4) Uani 0.5 1 d D U P B 1
F9 F 0.3394(19) 0.4440(13) 0.8198(6) 0.159(4) Uani 0.5 1 d D U P B 1
F10 F 0.398(2) 0.6041(15) 0.9036(6) 0.195(6) Uani 0.5 1 d D U P B 1
F11 F 0.570(3) 0.417(2) 0.9198(11) 0.236(10) Uani 0.5 1 d D U P B 1
F12 F 0.953(2) 0.5439(19) 0.8316(10) 0.244(6) Uani 0.5 1 d D U P B 1
F13 F 0.801(3) 0.6883(14) 0.9135(8) 0.211(6) Uani 0.5 1 d D U P B 1
F14 F 0.899(2) 0.4675(14) 0.9189(9) 0.239(7) Uani 0.5 1 d D U P B 1
C11' C 1.364(2) 1.0378(19) 0.8855(7) 0.154(3) Uani 0.5 1 d D U P A 2
C12' C 0.958(2) 1.0849(17) 0.8804(9) 0.150(3) Uani 0.5 1 d D U P A 2
C23' C 0.479(3) 0.4717(17) 0.8618(9) 0.153(3) Uani 0.5 1 d D U P B 2
C24' C 0.776(2) 0.6133(15) 0.9127(8) 0.158(3) Uani 0.5 1 d D U P B 2
F1' F 1.189(2) 1.1744(12) 0.8148(8) 0.157(5) Uani 0.5 1 d D U P A 2
F2' F 1.4523(19) 1.0440(18) 0.8276(9) 0.250(7) Uani 0.5 1 d D U P A 2
F3' F 1.315(3) 0.9300(17) 0.9109(10) 0.244(8) Uani 0.5 1 d D U P A 2
F4' F 1.350(2) 1.0882(14) 0.9597(6) 0.192(6) Uani 0.5 1 d D U P A 2
F5' F 1.026(6) 1.184(3) 0.9235(18) 0.376(19) Uani 0.5 1 d D U P A 2
F6' F 0.900(3) 0.9887(15) 0.9082(7) 0.184(6) Uani 0.5 1 d D U P A 2
F7' F 0.8409(16) 1.1373(12) 0.8276(6) 0.150(4) Uani 0.5 1 d D U P A 2
F8' F 0.809(2) 0.4608(15) 0.8299(8) 0.187(5) Uani 0.5 1 d D U P B 2
F9' F 0.478(3) 0.3840(12) 0.8090(7) 0.223(6) Uani 0.5 1 d D U P B 2
F10' F 0.471(3) 0.429(2) 0.9254(10) 0.202(7) Uani 0.5 1 d D U P B 2
F11' F 0.334(3) 0.541(2) 0.8621(13) 0.237(8) Uani 0.5 1 d D U P B 2
F12' F 0.9390(13) 0.6448(16) 0.8871(7) 0.179(5) Uani 0.5 1 d D U P B 2
F13' F 0.653(2) 0.6869(13) 0.9340(5) 0.195(5) Uani 0.5 1 d D U P B 2
F14' F 0.8288(18) 0.5377(14) 0.9607(6) 0.198(5) Uani 0.5 1 d D U P B 2
N1 N 0.7789(5) 1.0500(3) 0.5180(2) 0.0851(10) Uani 1 1 d . . . . .
N2 N 0.2765(5) 0.4542(3) 0.5163(2) 0.0846(10) Uani 1 1 d . . . . .
O1 O 0.8713(4) 1.0434(2) 0.58881(17) 0.0833(9) Uani 1 1 d . . . . .
O2 O 1.0151(5) 0.9987(3) 0.72414(17) 0.0906(9) Uani 1 1 d . . . . .
O3 O 0.5966(6) 0.9952(3) 0.37633(19) 0.1119(12) Uani 1 1 d . . . . .
O4 O 0.5764(4) 0.8035(2) 0.40156(15) 0.0825(9) Uani 1 1 d . . . . .
O5 O 0.3682(4) 0.4804(2) 0.58666(17) 0.0838(9) Uani 1 1 d . . . . .
O6 O 0.5132(5) 0.5620(3) 0.72165(17) 0.0922(9) Uani 1 1 d . . . . .
O7 O 0.0908(6) 0.4707(3) 0.37451(19) 0.1130(12) Uani 1 1 d . . . . .
O8 O 0.0744(4) 0.6699(2) 0.39882(15) 0.0838(9) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.312(5) . ?
C1 C2 1.410(5) . ?
C1 C8 1.449(6) . ?
C2 C3 1.351(5) . ?
C2 H2 0.9300 . ?
C3 O1 1.368(5) . ?
C3 C4 1.419(6) . ?
C4 O2 1.369(5) . ?
C4 C5 1.374(6) . ?
C5 C6 1.388(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.360(7) . ?
C6 H6 0.9300 . ?
C7 O2 1.348(6) . ?
C7 C10 1.501(7) . ?
C8 O3 1.205(5) . ?
C8 O4 1.320(5) . ?
C9 O4 1.441(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C12 1.506(16) . ?
C10 C11 1.510(15) . ?
C10 F1 1.571(14) . ?
C10 C11' 1.584(17) . ?
C10 C12' 1.589(16) . ?
C10 F1' 1.613(13) . ?
C13 N2 1.321(5) . ?
C13 C14 1.410(6) . ?
C13 C20 1.467(6) . ?
C14 C15 1.353(5) . ?
C14 H14 0.9300 . ?
C15 O5 1.373(5) . ?
C15 C16 1.433(6) . ?
C16 O6 1.355(5) . ?
C16 C17 1.358(6) . ?
C17 C18 1.392(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.360(7) . ?
C18 H18 0.9300 . ?
C19 O6 1.362(6) . ?
C19 C22 1.458(7) . ?
C20 O7 1.199(5) . ?
C20 O8 1.318(5) . ?
C21 O8 1.444(5) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C24' 1.533(16) . ?
C22 F8' 1.543(12) . ?
C22 C23' 1.553(16) . ?
C22 C24 1.562(17) . ?
C22 C23 1.618(17) . ?
C22 F8 1.655(11) . ?
C11 F4 1.371(16) . ?
C11 F2 1.400(14) . ?
C11 F3 1.494(15) . ?
C12 F7 1.330(16) . ?
C12 F6 1.330(16) . ?
C12 F5 1.354(15) . ?
C23 F9 1.331(16) . ?
C23 F10 1.358(17) . ?
C23 F11 1.421(17) . ?
C24 F12 1.327(17) . ?
C24 F14 1.370(15) . ?
C24 F13 1.420(16) . ?
C11' F2' 1.343(15) . ?
C11' F3' 1.384(17) . ?
C11' F4' 1.476(15) . ?
C12' F6' 1.315(17) . ?
C12' F7' 1.345(16) . ?
C12' F5' 1.347(18) . ?
C23' F11' 1.283(17) . ?
C23' F10' 1.323(16) . ?
C23' F9' 1.329(16) . ?
C24' F13' 1.283(16) . ?
C24' F14' 1.285(14) . ?
C24' F12' 1.376(15) . ?
N1 O1 1.383(5) . ?
N2 O5 1.375(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
N1 C1 C2 111.6(4) . . ?
N1 C1 C8 118.4(4) . . ?
C2 C1 C8 130.0(3) . . ?
C3 C2 C1 104.3(3) . . ?
C3 C2 H2 127.8 . . ?
C1 C2 H2 127.8 . . ?
C2 C3 O1 109.5(4) . . ?
C2 C3 C4 134.9(4) . . ?
O1 C3 C4 115.7(3) . . ?
O2 C4 C5 108.7(4) . . ?
O2 C4 C3 117.5(4) . . ?
C5 C4 C3 133.8(4) . . ?
C4 C5 C6 107.9(4) . . ?
C4 C5 H5 126.0 . . ?
C6 C5 H5 126.0 . . ?
C7 C6 C5 105.5(5) . . ?
C7 C6 H6 127.3 . . ?
C5 C6 H6 127.3 . . ?
O2 C7 C6 111.6(4) . . ?
O2 C7 C10 113.5(5) . . ?
C6 C7 C10 134.8(6) . . ?
O3 C8 O4 122.8(4) . . ?
O3 C8 C1 124.7(4) . . ?
O4 C8 C1 112.4(3) . . ?
O4 C9 H9A 109.5 . . ?
O4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 C12 113.2(8) . . ?
C7 C10 C11 117.3(8) . . ?
C12 C10 C11 118.2(9) . . ?
C7 C10 F1 107.5(8) . . ?
C12 C10 F1 107.8(11) . . ?
C11 C10 F1 88.7(9) . . ?
C7 C10 C11' 110.7(8) . . ?
C7 C10 C12' 108.1(8) . . ?
C11' C10 C12' 132.8(9) . . ?
C7 C10 F1' 108.0(7) . . ?
C11' C10 F1' 92.4(10) . . ?
C12' C10 F1' 100.2(10) . . ?
N2 C13 C14 111.8(4) . . ?
N2 C13 C20 118.1(4) . . ?
C14 C13 C20 130.0(3) . . ?
C15 C14 C13 104.1(3) . . ?
C15 C14 H14 127.9 . . ?
C13 C14 H14 127.9 . . ?
C14 C15 O5 109.4(4) . . ?
C14 C15 C16 135.0(4) . . ?
O5 C15 C16 115.6(3) . . ?
O6 C16 C17 109.8(4) . . ?
O6 C16 C15 117.0(3) . . ?
C17 C16 C15 133.2(4) . . ?
C16 C17 C18 107.6(4) . . ?
C16 C17 H17 126.2 . . ?
C18 C17 H17 126.2 . . ?
C19 C18 C17 105.9(5) . . ?
C19 C18 H18 127.1 . . ?
C17 C18 H18 127.1 . . ?
C18 C19 O6 110.5(4) . . ?
C18 C19 C22 134.4(6) . . ?
O6 C19 C22 115.1(5) . . ?
O7 C20 O8 124.0(4) . . ?
O7 C20 C13 124.4(4) . . ?
O8 C20 C13 111.6(3) . . ?
O8 C21 H21A 109.5 . . ?
O8 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O8 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 C24' 114.7(8) . . ?
C19 C22 F8' 110.3(7) . . ?
C24' C22 F8' 93.5(10) . . ?
C19 C22 C23' 112.6(9) . . ?
C24' C22 C23' 115.8(10) . . ?
F8' C22 C23' 108.0(11) . . ?
C19 C22 C24 113.4(8) . . ?
C19 C22 C23 110.8(8) . . ?
C24 C22 C23 131.0(9) . . ?
C19 C22 F8 106.9(6) . . ?
C24 C22 F8 94.3(9) . . ?
C23 C22 F8 92.4(9) . . ?
F4 C11 F2 110.6(13) . . ?
F4 C11 F3 146.2(14) . . ?
F2 C11 F3 95.1(13) . . ?
F4 C11 C10 95.0(10) . . ?
F2 C11 C10 108.7(11) . . ?
F3 C11 C10 97.3(12) . . ?
F7 C12 F6 119.6(19) . . ?
F7 C12 F5 115.7(17) . . ?
F6 C12 F5 102.0(16) . . ?
F7 C12 C10 100.8(14) . . ?
F6 C12 C10 107.4(13) . . ?
F5 C12 C10 111.3(12) . . ?
F9 C23 F10 114.5(16) . . ?
F9 C23 F11 113.6(18) . . ?
F10 C23 F11 120.7(17) . . ?
F9 C23 C22 110.8(12) . . ?
F10 C23 C22 100.1(13) . . ?
F11 C23 C22 93.4(12) . . ?
F12 C24 F14 95.0(17) . . ?
F12 C24 F13 130.3(18) . . ?
F14 C24 F13 131.5(17) . . ?
F12 C24 C22 99.2(13) . . ?
F14 C24 C22 101.4(13) . . ?
F13 C24 C22 88.9(12) . . ?
F2' C11' F3' 124(2) . . ?
F2' C11' F4' 146.7(18) . . ?
F3' C11' F4' 83.5(14) . . ?
F2' C11' C10 100.7(12) . . ?
F3' C11' C10 88.2(13) . . ?
F4' C11' C10 98.9(11) . . ?
F6' C12' F7' 120.3(18) . . ?
F6' C12' F5' 121(2) . . ?
F7' C12' F5' 100(2) . . ?
F6' C12' C10 107.6(14) . . ?
F7' C12' C10 106.5(12) . . ?
F5' C12' C10 99(2) . . ?
F11' C23' F10' 95.5(18) . . ?
F11' C23' F9' 120(2) . . ?
F10' C23' F9' 112.4(17) . . ?
F11' C23' C22 108.1(15) . . ?
F10' C23' C22 124.3(16) . . ?
F9' C23' C22 98.3(12) . . ?
F13' C24' F14' 110.4(15) . . ?
F13' C24' F12' 126.0(17) . . ?
F14' C24' F12' 106.0(14) . . ?
F13' C24' C22 99.6(12) . . ?
F14' C24' C22 110.0(13) . . ?
F12' C24' C22 103.8(12) . . ?
C1 N1 O1 106.3(3) . . ?
C13 N2 O5 106.0(3) . . ?
C3 O1 N1 108.3(3) . . ?
C7 O2 C4 106.3(4) . . ?
C8 O4 C9 116.3(3) . . ?
C15 O5 N2 108.7(3) . . ?
C16 O6 C19 106.3(4) . . ?
C20 O8 C21 116.1(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
N1 C1 C2 C3 0.5(4) . . . . ?
C8 C1 C2 C3 -178.7(4) . . . . ?
C1 C2 C3 O1 0.0(4) . . . . ?
C1 C2 C3 C4 178.6(4) . . . . ?
C2 C3 C4 O2 -170.2(4) . . . . ?
O1 C3 C4 O2 8.4(5) . . . . ?
C2 C3 C4 C5 8.5(8) . . . . ?
O1 C3 C4 C5 -172.9(4) . . . . ?
O2 C4 C5 C6 1.1(5) . . . . ?
C3 C4 C5 C6 -177.7(4) . . . . ?
C4 C5 C6 C7 -1.5(5) . . . . ?
C5 C6 C7 O2 1.4(6) . . . . ?
C5 C6 C7 C10 178.5(6) . . . . ?
N1 C1 C8 O3 6.8(6) . . . . ?
C2 C1 C8 O3 -174.0(4) . . . . ?
N1 C1 C8 O4 -172.8(3) . . . . ?
C2 C1 C8 O4 6.4(6) . . . . ?
O2 C7 C10 C12 61.0(11) . . . . ?
C6 C7 C10 C12 -116.1(11) . . . . ?
O2 C7 C10 C11 -155.9(8) . . . . ?
C6 C7 C10 C11 27.0(12) . . . . ?
O2 C7 C10 F1 -58.0(9) . . . . ?
C6 C7 C10 F1 124.8(10) . . . . ?
O2 C7 C10 C11' -127.0(9) . . . . ?
C6 C7 C10 C11' 55.9(11) . . . . ?
O2 C7 C10 C12' 80.4(9) . . . . ?
C6 C7 C10 C12' -96.7(10) . . . . ?
O2 C7 C10 F1' -27.2(9) . . . . ?
C6 C7 C10 F1' 155.7(9) . . . . ?
N2 C13 C14 C15 -0.1(4) . . . . ?
C20 C13 C14 C15 178.9(4) . . . . ?
C13 C14 C15 O5 -0.3(4) . . . . ?
C13 C14 C15 C16 -179.4(4) . . . . ?
C14 C15 C16 O6 170.2(4) . . . . ?
O5 C15 C16 O6 -8.8(5) . . . . ?
C14 C15 C16 C17 -7.3(8) . . . . ?
O5 C15 C16 C17 173.7(4) . . . . ?
O6 C16 C17 C18 0.2(5) . . . . ?
C15 C16 C17 C18 177.9(4) . . . . ?
C16 C17 C18 C19 -0.1(5) . . . . ?
C17 C18 C19 O6 -0.1(6) . . . . ?
C17 C18 C19 C22 -179.2(7) . . . . ?
N2 C13 C20 O7 -5.2(6) . . . . ?
C14 C13 C20 O7 175.9(4) . . . . ?
N2 C13 C20 O8 173.2(3) . . . . ?
C14 C13 C20 O8 -5.8(6) . . . . ?
C18 C19 C22 C24' -12.9(13) . . . . ?
O6 C19 C22 C24' 168.0(8) . . . . ?
C18 C19 C22 F8' -116.9(11) . . . . ?
O6 C19 C22 F8' 64.1(11) . . . . ?
C18 C19 C22 C23' 122.4(10) . . . . ?
O6 C19 C22 C23' -56.7(11) . . . . ?
C18 C19 C22 C24 -51.0(12) . . . . ?
O6 C19 C22 C24 129.9(9) . . . . ?
C18 C19 C22 C23 107.2(10) . . . . ?
O6 C19 C22 C23 -71.9(9) . . . . ?
C18 C19 C22 F8 -153.5(8) . . . . ?
O6 C19 C22 F8 27.4(9) . . . . ?
C7 C10 C11 F4 -66.8(11) . . . . ?
C12 C10 C11 F4 74.5(13) . . . . ?
F1 C10 C11 F4 -175.9(11) . . . . ?
C11' C10 C11 F4 -149(2) . . . . ?
C12' C10 C11 F4 56.5(12) . . . . ?
F1' C10 C11 F4 166.8(10) . . . . ?
C7 C10 C11 F2 46.9(14) . . . . ?
C12 C10 C11 F2 -171.8(12) . . . . ?
F1 C10 C11 F2 -62.2(13) . . . . ?
C11' C10 C11 F2 -35.4(17) . . . . ?
C12' C10 C11 F2 170.1(12) . . . . ?
F1' C10 C11 F2 -79.5(13) . . . . ?
C7 C10 C11 F3 144.8(10) . . . . ?
C12 C10 C11 F3 -73.9(14) . . . . ?
F1 C10 C11 F3 35.7(11) . . . . ?
C11' C10 C11 F3 63(2) . . . . ?
C12' C10 C11 F3 -91.9(13) . . . . ?
F1' C10 C11 F3 18.4(14) . . . . ?
C7 C10 C12 F7 -74.1(16) . . . . ?
C11 C10 C12 F7 143.1(14) . . . . ?
F1 C10 C12 F7 44.8(16) . . . . ?
C11' C10 C12 F7 116.6(18) . . . . ?
C12' C10 C12 F7 -152(4) . . . . ?
F1' C10 C12 F7 31.9(14) . . . . ?
C7 C10 C12 F6 51.8(17) . . . . ?
C11 C10 C12 F6 -91.0(16) . . . . ?
F1 C10 C12 F6 170.7(14) . . . . ?
C11' C10 C12 F6 -117.5(18) . . . . ?
C12' C10 C12 F6 -26(3) . . . . ?
F1' C10 C12 F6 157.8(15) . . . . ?
C7 C10 C12 F5 162.7(12) . . . . ?
C11 C10 C12 F5 19.9(19) . . . . ?
F1 C10 C12 F5 -78.4(16) . . . . ?
C11' C10 C12 F5 -7(2) . . . . ?
C12' C10 C12 F5 85(4) . . . . ?
F1' C10 C12 F5 -91.3(15) . . . . ?
C19 C22 C23 F9 52.8(16) . . . . ?
C24' C22 C23 F9 177.9(14) . . . . ?
F8' C22 C23 F9 -78.1(16) . . . . ?
C23' C22 C23 F9 -47(4) . . . . ?
C24 C22 C23 F9 -154.0(14) . . . . ?
F8 C22 C23 F9 -56.3(14) . . . . ?
C19 C22 C23 F10 -68.3(12) . . . . ?
C24' C22 C23 F10 56.7(13) . . . . ?
F8' C22 C23 F10 160.8(11) . . . . ?
C23' C22 C23 F10 -168(5) . . . . ?
C24 C22 C23 F10 84.8(15) . . . . ?
F8 C22 C23 F10 -177.4(10) . . . . ?
C19 C22 C23 F11 169.7(13) . . . . ?
C24' C22 C23 F11 -65.2(16) . . . . ?
F8' C22 C23 F11 38.8(17) . . . . ?
C23' C22 C23 F11 70(5) . . . . ?
C24 C22 C23 F11 -37(2) . . . . ?
F8 C22 C23 F11 60.6(14) . . . . ?
C19 C22 C24 F12 -61.1(14) . . . . ?
C24' C22 C24 F12 -161(2) . . . . ?
F8' C22 C24 F12 39.9(12) . . . . ?
C23' C22 C24 F12 127.2(16) . . . . ?
C23 C22 C24 F12 146.2(14) . . . . ?
F8 C22 C24 F12 49.3(13) . . . . ?
C19 C22 C24 F14 -158.2(12) . . . . ?
C24' C22 C24 F14 102(2) . . . . ?
F8' C22 C24 F14 -57.2(13) . . . . ?
C23' C22 C24 F14 30(2) . . . . ?
C23 C22 C24 F14 49.2(19) . . . . ?
F8 C22 C24 F14 -47.7(14) . . . . ?
C19 C22 C24 F13 69.6(13) . . . . ?
C24' C22 C24 F13 -30.5(13) . . . . ?
F8' C22 C24 F13 170.6(14) . . . . ?
C23' C22 C24 F13 -102.0(17) . . . . ?
C23 C22 C24 F13 -83.0(16) . . . . ?
F8 C22 C24 F13 -180.0(12) . . . . ?
C7 C10 C11' F2' 55.5(16) . . . . ?
C12 C10 C11' F2' -134.9(17) . . . . ?
C11 C10 C11' F2' 165(3) . . . . ?
F1 C10 C11' F2' -44.7(14) . . . . ?
C12' C10 C11' F2' -161.0(14) . . . . ?
F1' C10 C11' F2' -54.7(15) . . . . ?
C7 C10 C11' F3' -68.5(13) . . . . ?
C12 C10 C11' F3' 101.1(19) . . . . ?
C11 C10 C11' F3' 41.2(19) . . . . ?
F1 C10 C11' F3' -168.7(15) . . . . ?
C12' C10 C11' F3' 74.9(19) . . . . ?
F1' C10 C11' F3' -178.7(13) . . . . ?
C7 C10 C11' F4' -151.6(11) . . . . ?
C12 C10 C11' F4' 18(2) . . . . ?
C11 C10 C11' F4' -41.9(16) . . . . ?
F1 C10 C11' F4' 108.2(15) . . . . ?
C12' C10 C11' F4' -8(2) . . . . ?
F1' C10 C11' F4' 98.1(14) . . . . ?
C7 C10 C12' F6' 64.7(14) . . . . ?
C12 C10 C12' F6' 174(4) . . . . ?
C11 C10 C12' F6' -63.8(15) . . . . ?
F1 C10 C12' F6' -166.5(13) . . . . ?
C11' C10 C12' F6' -79(2) . . . . ?
F1' C10 C12' F6' 177.6(13) . . . . ?
C7 C10 C12' F7' -65.6(15) . . . . ?
C12 C10 C12' F7' 44(3) . . . . ?
C11 C10 C12' F7' 165.8(13) . . . . ?
F1 C10 C12' F7' 63.1(18) . . . . ?
C11' C10 C12' F7' 150.3(15) . . . . ?
F1' C10 C12' F7' 47.3(14) . . . . ?
C7 C10 C12' F5' -169(2) . . . . ?
C12 C10 C12' F5' -60(3) . . . . ?
C11 C10 C12' F5' 63(2) . . . . ?
F1 C10 C12' F5' -40(2) . . . . ?
C11' C10 C12' F5' 47(3) . . . . ?
F1' C10 C12' F5' -56(2) . . . . ?
C19 C22 C23' F11' -46.3(19) . . . . ?
C24' C22 C23' F11' 88.4(18) . . . . ?
F8' C22 C23' F11' -168.4(16) . . . . ?
C24 C22 C23' F11' 125.3(18) . . . . ?
C23 C22 C23' F11' 40(4) . . . . ?
F8 C22 C23' F11' -149.9(18) . . . . ?
C19 C22 C23' F10' -156.4(18) . . . . ?
C24' C22 C23' F10' -22(2) . . . . ?
F8' C22 C23' F10' 82(2) . . . . ?
C24 C22 C23' F10' 15(3) . . . . ?
C23 C22 C23' F10' -71(5) . . . . ?
F8 C22 C23' F10' 100(2) . . . . ?
C19 C22 C23' F9' 79.1(15) . . . . ?
C24' C22 C23' F9' -146.2(14) . . . . ?
F8' C22 C23' F9' -43.0(16) . . . . ?
C24 C22 C23' F9' -109.3(17) . . . . ?
C23 C22 C23' F9' 165(6) . . . . ?
F8 C22 C23' F9' -24.5(13) . . . . ?
C19 C22 C24' F13' 68.8(12) . . . . ?
F8' C22 C24' F13' -177.0(11) . . . . ?
C23' C22 C24' F13' -65.0(15) . . . . ?
C24 C22 C24' F13' 165(2) . . . . ?
C23 C22 C24' F13' -53.9(13) . . . . ?
F8 C22 C24' F13' -157.9(10) . . . . ?
C19 C22 C24' F14' -175.3(11) . . . . ?
F8' C22 C24' F14' -61.0(14) . . . . ?
C23' C22 C24' F14' 50.9(18) . . . . ?
C24 C22 C24' F14' -79(2) . . . . ?
C23 C22 C24' F14' 62.1(16) . . . . ?
F8 C22 C24' F14' -41.9(17) . . . . ?
C19 C22 C24' F12' -62.2(14) . . . . ?
F8' C22 C24' F12' 52.1(13) . . . . ?
C23' C22 C24' F12' 164.0(13) . . . . ?
C24 C22 C24' F12' 33.7(12) . . . . ?
C23 C22 C24' F12' 175.1(12) . . . . ?
F8 C22 C24' F12' 71.1(14) . . . . ?
C2 C1 N1 O1 -0.7(4) . . . . ?
C8 C1 N1 O1 178.6(3) . . . . ?
C14 C13 N2 O5 0.4(4) . . . . ?
C20 C13 N2 O5 -178.7(3) . . . . ?
C2 C3 O1 N1 -0.4(4) . . . . ?
C4 C3 O1 N1 -179.3(3) . . . . ?
C1 N1 O1 C3 0.7(4) . . . . ?
C6 C7 O2 C4 -0.7(5) . . . . ?
C10 C7 O2 C4 -178.6(4) . . . . ?
C5 C4 O2 C7 -0.2(5) . . . . ?
C3 C4 O2 C7 178.8(3) . . . . ?
O3 C8 O4 C9 -1.8(6) . . . . ?
C1 C8 O4 C9 177.9(3) . . . . ?
C14 C15 O5 N2 0.6(4) . . . . ?
C16 C15 O5 N2 179.8(3) . . . . ?
C13 N2 O5 C15 -0.6(4) . . . . ?
C17 C16 O6 C19 -0.3(5) . . . . ?
C15 C16 O6 C19 -178.4(3) . . . . ?
C18 C19 O6 C16 0.2(5) . . . . ?
C22 C19 O6 C16 179.5(5) . . . . ?
O7 C20 O8 C21 0.5(6) . . . . ?
C13 C20 O8 C21 -177.8(3) . . . . ?

_refine_diff_density_max         0.550
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.082

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_d8v21857
_database_code_depnum_ccdc_archive 'CCDC 2142018'
loop_
_audit_author_name
_audit_author_address
'chaolai tong'
;Shanghai institute of Organic Chemistry,Chinese Academy of Sciences
China
;
_audit_update_record             
;
2022-01-14 deposited with the CCDC.	2022-07-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H7 F7 N2 O2'
_chemical_formula_weight         308.17

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   13.3881(15)
_cell_length_b                   13.9966(16)
_cell_length_c                   7.0375(8)
_cell_angle_alpha                90
_cell_angle_beta                 111.114(4)
_cell_angle_gamma                90
_cell_volume                     1230.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5047
_cell_measurement_theta_min      4.371
_cell_measurement_theta_max      51.321

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.186
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6347
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8963
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         4.374
_diffrn_reflns_theta_max         25.969
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_point_group_measured_fraction_full 0.947
_reflns_number_total             2287
_reflns_number_gt                1913
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.919
_reflns_Friedel_fraction_max     0.907
_reflns_Friedel_fraction_full    0.914

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0860P)²+0.1960P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 811 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.5(3)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2287
_refine_ls_number_parameters     264
_refine_ls_number_restraints     92
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1412
_refine_ls_wR_factor_gt          0.1305
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.164
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3371(2) 0.7313(3) 0.4105(6) 0.0910(11) Uani 1 1 d . . . . .
O2 O 0.4944(3) 0.5125(3) 0.9048(6) 0.1005(12) Uani 1 1 d . . . . .
N1 N 0.4148(3) 0.6226(3) 0.6587(5) 0.0669(8) Uani 1 1 d . . . . .
N2 N 0.6003(3) 0.6104(3) 0.8046(5) 0.0711(9) Uani 1 1 d . . . . .
C1 C 0.4187(3) 0.6940(3) 0.5245(6) 0.0626(9) Uani 1 1 d . . . . .
C2 C 0.5016(4) 0.5774(3) 0.7955(6) 0.0687(10) Uani 1 1 d . . . . .
C3 C 0.6096(3) 0.6788(3) 0.6760(6) 0.0671(9) Uani 1 1 d . . . . .
H5 H 0.6778 0.6978 0.6855 0.081 Uiso 1 1 calc R U . . .
C4 C 0.5250(3) 0.7201(2) 0.5359(5) 0.0586(8) Uani 1 1 d . . . . .
C5 C 0.3092(5) 0.5876(5) 0.6462(10) 0.1054(18) Uani 1 1 d . . . . .
H5A H 0.3160 0.5238 0.6995 0.158 Uiso 1 1 calc R U . . .
H5B H 0.2614 0.5875 0.5066 0.158 Uiso 1 1 calc R U . . .
H5C H 0.2811 0.6285 0.7244 0.158 Uiso 1 1 calc R U . . .
C6 C 0.6967(5) 0.5671(5) 0.9548(10) 0.113(2) Uani 1 1 d . . . . .
H6A H 0.7488 0.5560 0.8928 0.170 Uiso 1 1 calc R U . . .
H6B H 0.6781 0.5075 1.0010 0.170 Uiso 1 1 calc R U . . .
H6C H 0.7260 0.6096 1.0686 0.170 Uiso 1 1 calc R U . . .
C7 C 0.5438(4) 0.7935(3) 0.3958(7) 0.0803(12) Uani 1 1 d D . . . .
F1 F 0.6473(5) 0.7699(6) 0.3811(12) 0.106(2) Uani 0.6 1 d . . P A 1
F2 F 0.4403(12) 0.6940(7) 0.112(2) 0.124(4) Uani 0.6 1 d D U P A 1
F3 F 0.3826(5) 0.8378(5) 0.1223(9) 0.1129(19) Uani 0.6 1 d D U P A 1
F4 F 0.5196(12) 0.8056(8) 0.0371(16) 0.133(3) Uani 0.6 1 d D U P A 1
F5 F 0.4646(9) 0.9170(8) 0.4892(18) 0.118(3) Uani 0.6 1 d D U P A 1
F6 F 0.5759(9) 0.9505(7) 0.3391(18) 0.134(3) Uani 0.6 1 d D U P A 1
F7 F 0.6330(5) 0.8977(4) 0.6454(10) 0.1117(19) Uani 0.6 1 d D U P A 1
C8 C 0.4701(12) 0.7830(9) 0.1659(17) 0.107(3) Uani 0.6 1 d D U P A 1
C9 C 0.5549(8) 0.8908(6) 0.4704(15) 0.099(3) Uani 0.6 1 d D U P A 1
F1' F 0.6497(8) 0.8311(11) 0.495(2) 0.126(4) Uani 0.4 1 d . . P A 2
F2' F 0.6004(13) 0.6992(11) 0.215(2) 0.160(4) Uani 0.4 1 d D U P A 2
F3' F 0.5382(18) 0.8424(11) 0.085(2) 0.134(5) Uani 0.4 1 d D U P A 2
F4' F 0.427(2) 0.7287(17) 0.107(4) 0.143(6) Uani 0.4 1 d D U P A 2
F5' F 0.4602(18) 0.9057(13) 0.571(2) 0.118(4) Uani 0.4 1 d D U P A 2
F6' F 0.3843(11) 0.8975(8) 0.245(2) 0.137(3) Uani 0.4 1 d D U P A 2
F7' F 0.5324(15) 0.9706(11) 0.381(3) 0.135(5) Uani 0.4 1 d D U P A 2
C8' C 0.524(2) 0.7650(17) 0.193(3) 0.136(5) Uani 0.4 1 d D U P A 2
C9' C 0.4786(19) 0.8933(13) 0.399(3) 0.125(4) Uani 0.4 1 d D U P A 2


_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
O1 C1 1.216(5) . ?
O2 C2 1.217(5) . ?
N1 C2 1.369(6) . ?
N1 C1 1.388(5) . ?
N1 C5 1.470(6) . ?
N2 C3 1.354(5) . ?
N2 C2 1.378(6) . ?
N2 C6 1.472(6) . ?
C1 C4 1.442(5) . ?
C3 C4 1.336(5) . ?
C3 H5 0.9300 . ?
C4 C7 1.507(6) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8' 1.414(19) . ?
C7 F1' 1.436(11) . ?
C7 C9 1.448(10) . ?
C7 F1 1.464(7) . ?
C7 C8 1.569(13) . ?
C7 C9' 1.65(2) . ?
F2 C8 1.322(16) . ?
F3 C8 1.339(15) . ?
F4 C8 1.339(16) . ?
F5 C9 1.315(15) . ?
F6 C9 1.349(13) . ?
F7 C9 1.301(11) . ?
F2' C8' 1.35(2) . ?
F3' C8' 1.38(2) . ?
F4' C8' 1.32(2) . ?
F5' C9' 1.33(2) . ?
F6' C9' 1.33(2) . ?
F7' C9' 1.33(2) . ?

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
C2 N1 C1 125.5(3) . . ?
C2 N1 C5 116.3(4) . . ?
C1 N1 C5 118.1(4) . . ?
C3 N2 C2 121.5(3) . . ?
C3 N2 C6 120.2(4) . . ?
C2 N2 C6 118.2(4) . . ?
O1 C1 N1 120.8(4) . . ?
O1 C1 C4 124.2(4) . . ?
N1 C1 C4 115.0(3) . . ?
O2 C2 N1 123.3(4) . . ?
O2 C2 N2 120.9(4) . . ?
N1 C2 N2 115.8(3) . . ?
C4 C3 N2 122.8(4) . . ?
C4 C3 H5 118.6 . . ?
N2 C3 H5 118.6 . . ?
C3 C4 C1 119.3(3) . . ?
C3 C4 C7 118.7(3) . . ?
C1 C4 C7 122.0(3) . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8' C7 F1' 113.0(12) . . ?
C9 C7 F1 105.2(7) . . ?
C8' C7 C4 117.0(10) . . ?
F1' C7 C4 107.4(5) . . ?
C9 C7 C4 115.1(6) . . ?
F1 C7 C4 106.1(4) . . ?
C9 C7 C8 114.0(7) . . ?
F1 C7 C8 99.5(7) . . ?
C4 C7 C8 114.8(6) . . ?
C8' C7 C9' 110.0(12) . . ?
F1' C7 C9' 96.8(11) . . ?
C4 C7 C9' 110.9(8) . . ?
F2 C8 F3 109.0(13) . . ?
F2 C8 F4 101.5(13) . . ?
F3 C8 F4 108.3(11) . . ?
F2 C8 C7 113.5(10) . . ?
F3 C8 C7 110.8(9) . . ?
F4 C8 C7 113.3(11) . . ?
F7 C9 F5 109.8(11) . . ?
F7 C9 F6 107.9(9) . . ?
F5 C9 F6 108.8(10) . . ?
F7 C9 C7 110.8(7) . . ?
F5 C9 C7 108.7(8) . . ?
F6 C9 C7 110.7(9) . . ?
F4' C8' F2' 112(2) . . ?
F4' C8' F3' 111.2(19) . . ?
F2' C8' F3' 110.5(17) . . ?
F4' C8' C7 111.7(18) . . ?
F2' C8' C7 102.5(16) . . ?
F3' C8' C7 108.8(16) . . ?
F7' C9' F5' 105.2(19) . . ?
F7' C9' F6' 106.0(17) . . ?
F5' C9' F6' 107(2) . . ?
F7' C9' C7 112.4(17) . . ?
F5' C9' C7 113.1(14) . . ?
F6' C9' C7 112.2(14) . . ?

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
C2 N1 C1 O1 -178.7(4) . . . . ?
C5 N1 C1 O1 5.4(6) . . . . ?
C2 N1 C1 C4 0.1(5) . . . . ?
C5 N1 C1 C4 -175.8(4) . . . . ?
C1 N1 C2 O2 -177.0(4) . . . . ?
C5 N1 C2 O2 -1.0(7) . . . . ?
C1 N1 C2 N2 3.5(6) . . . . ?
C5 N1 C2 N2 179.5(4) . . . . ?
C3 N2 C2 O2 176.1(4) . . . . ?
C6 N2 C2 O2 -1.9(7) . . . . ?
C3 N2 C2 N1 -4.3(6) . . . . ?
C6 N2 C2 N1 177.6(5) . . . . ?
C2 N2 C3 C4 1.5(6) . . . . ?
C6 N2 C3 C4 179.6(5) . . . . ?
N2 C3 C4 C1 2.4(6) . . . . ?
N2 C3 C4 C7 -178.3(4) . . . . ?
O1 C1 C4 C3 175.7(4) . . . . ?
N1 C1 C4 C3 -3.1(5) . . . . ?
O1 C1 C4 C7 -3.6(6) . . . . ?
N1 C1 C4 C7 177.6(4) . . . . ?
C3 C4 C7 C8' 105.4(12) . . . . ?
C1 C4 C7 C8' -75.3(12) . . . . ?
C3 C4 C7 F1' -22.8(9) . . . . ?
C1 C4 C7 F1' 156.5(8) . . . . ?
C3 C4 C7 C9 -89.0(6) . . . . ?
C1 C4 C7 C9 90.3(6) . . . . ?
C3 C4 C7 F1 26.9(6) . . . . ?
C1 C4 C7 F1 -153.8(5) . . . . ?
C3 C4 C7 C8 135.7(7) . . . . ?
C1 C4 C7 C8 -45.0(8) . . . . ?
C3 C4 C7 C9' -127.4(9) . . . . ?
C1 C4 C7 C9' 51.9(9) . . . . ?
C8' C7 C8 F2 72(3) . . . . ?
F1' C7 C8 F2 122.1(15) . . . . ?
C9 C7 C8 F2 -165.2(12) . . . . ?
F1 C7 C8 F2 83.4(13) . . . . ?
C4 C7 C8 F2 -29.4(15) . . . . ?
C9' C7 C8 F2 -141.1(15) . . . . ?
C8' C7 C8 F3 -165(3) . . . . ?
F1' C7 C8 F3 -114.9(13) . . . . ?
C9 C7 C8 F3 -42.2(13) . . . . ?
F1 C7 C8 F3 -153.6(9) . . . . ?
C4 C7 C8 F3 93.6(9) . . . . ?
C9' C7 C8 F3 -18.2(11) . . . . ?
C8' C7 C8 F4 -43(2) . . . . ?
F1' C7 C8 F4 7.1(18) . . . . ?
C9 C7 C8 F4 79.8(13) . . . . ?
F1 C7 C8 F4 -31.6(12) . . . . ?
C4 C7 C8 F4 -144.4(10) . . . . ?
C9' C7 C8 F4 103.8(13) . . . . ?
C8' C7 C9 F7 -138.3(14) . . . . ?
F1' C7 C9 F7 -39.4(9) . . . . ?
F1 C7 C9 F7 -58.7(10) . . . . ?
C4 C7 C9 F7 57.7(11) . . . . ?
C8 C7 C9 F7 -166.7(9) . . . . ?
C9' C7 C9 F7 148.8(18) . . . . ?
C8' C7 C9 F5 100.9(15) . . . . ?
F1' C7 C9 F5 -160.1(10) . . . . ?
F1 C7 C9 F5 -179.5(7) . . . . ?
C4 C7 C9 F5 -63.1(9) . . . . ?
C8 C7 C9 F5 72.5(11) . . . . ?
C9' C7 C9 F5 28.0(12) . . . . ?
C8' C7 C9 F6 -18.6(17) . . . . ?
F1' C7 C9 F6 80.4(10) . . . . ?
F1 C7 C9 F6 61.0(9) . . . . ?
C4 C7 C9 F6 177.4(7) . . . . ?
C8 C7 C9 F6 -46.9(13) . . . . ?
C9' C7 C9 F6 -91.4(15) . . . . ?
F1' C7 C8' F4' 178.5(18) . . . . ?
C9 C7 C8' F4' -110.8(19) . . . . ?
F1 C7 C8' F4' 153(2) . . . . ?
C4 C7 C8' F4' 53(2) . . . . ?
C8 C7 C8' F4' -39.3(18) . . . . ?
C9' C7 C8' F4' -75(2) . . . . ?
F1' C7 C8' F2' 58.6(17) . . . . ?
C9 C7 C8' F2' 129.4(13) . . . . ?
F1 C7 C8' F2' 32.8(12) . . . . ?
C4 C7 C8' F2' -66.9(17) . . . . ?
C8 C7 C8' F2' -159(3) . . . . ?
C9' C7 C8' F2' 165.5(13) . . . . ?
F1' C7 C8' F3' -58.4(19) . . . . ?
C9 C7 C8' F3' 12(2) . . . . ?
F1 C7 C8' F3' -84.2(16) . . . . ?
C4 C7 C8' F3' 176.1(13) . . . . ?
C8 C7 C8' F3' 84(3) . . . . ?
C9' C7 C8' F3' 48(2) . . . . ?
C8' C7 C9' F7' -85(2) . . . . ?
F1' C7 C9' F7' 32.9(18) . . . . ?
C9 C7 C9' F7' 40.1(15) . . . . ?
F1 C7 C9' F7' 1(2) . . . . ?
C4 C7 C9' F7' 144.5(15) . . . . ?
C8 C7 C9' F7' -100.0(17) . . . . ?
C8' C7 C9' F5' 156.5(19) . . . . ?
F1' C7 C9' F5' -86.0(19) . . . . ?
C9 C7 C9' F5' -79(2) . . . . ?
F1 C7 C9' F5' -118.1(17) . . . . ?
C4 C7 C9' F5' 26(2) . . . . ?
C8 C7 C9' F5' 141.1(19) . . . . ?
C8' C7 C9' F6' 34.8(19) . . . . ?
F1' C7 C9' F6' 152.3(14) . . . . ?
C9 C7 C9' F6' 160(2) . . . . ?
F1 C7 C9' F6' 120.2(14) . . . . ?
C4 C7 C9' F6' -96.1(13) . . . . ?
C8 C7 C9' F6' 19.4(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6C F2' 0.96 2.59 3.183(15) 120.2 1_556
C6 H6A F6' 0.96 2.48 3.377(17) 155.4 4_565
C5 H5B F7 0.96 2.51 3.469(8) 175.0 4_464
C3 H5 O1 0.93 2.37 3.157(4) 142.4 4_565
C6 H6C F2' 0.96 2.59 3.183(15) 120.2 1_556
C6 H6A F6' 0.96 2.48 3.377(17) 155.4 4_565
C6 H6A F5' 0.96 2.70 3.34(2) 124.6 4_565
C5 H5B F7 0.96 2.51 3.469(8) 175.0 4_464
C3 H5 O1 0.93 2.37 3.157(4) 142.4 4_565
C6 H6C F2' 0.96 2.59 3.183(15) 120.2 1_556
C6 H6A F6' 0.96 2.48 3.377(17) 155.4 4_565
C6 H6A F5' 0.96 2.70 3.34(2) 124.6 4_565
C6 H6A F5 0.96 2.74 3.514(14) 137.6 4_565
C5 H5B F7 0.96 2.51 3.469(8) 175.0 4_464
C3 H5 O1 0.93 2.37 3.157(4) 142.4 4_565
C6 H6C F2' 0.96 2.59 3.183(15) 120.2 1_556
C6 H6A F6' 0.96 2.48 3.377(17) 155.4 4_565
C6 H6A F5' 0.96 2.70 3.34(2) 124.6 4_565
C6 H6A F5 0.96 2.74 3.514(14) 137.6 4_565
C5 H5B F7 0.96 2.51 3.469(8) 175.0 4_464
C3 H5 O1 0.93 2.37 3.157(4) 142.4 4_565
C3 H5 O1 0.93 2.37 3.157(4) 142.4 4_565
C5 H5B F7 0.96 2.51 3.469(8) 175.0 4_464
C6 H6A F5 0.96 2.74 3.514(14) 137.6 4_565
C6 H6A F5' 0.96 2.70 3.34(2) 124.6 4_565
C6 H6A F6' 0.96 2.48 3.377(17) 155.4 4_565
C6 H6C F2' 0.96 2.59 3.183(15) 120.2 1_556
C3 H5 O1 0.93 2.37 3.157(4) 142.4 4_565
C5 H5B F7 0.96 2.51 3.469(8) 175.0 4_464
C6 H6A F6' 0.96 2.48 3.377(17) 155.4 4_565
C6 H6C F2' 0.96 2.59 3.183(15) 120.2 1_556
C3 H5 O1 0.93 2.37 3.157(4) 142.4 4_565
C5 H5B F7 0.96 2.51 3.469(8) 175.0 4_464
C6 H6A F6' 0.96 2.48 3.377(17) 155.4 4_565
C6 H6C F2' 0.96 2.59 3.183(15) 120.2 1_556

_refine_diff_density_max         0.161
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.038

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_mo_d8v21841_0m
_database_code_depnum_ccdc_archive 'CCDC 2142021'
loop_
_audit_author_name
_audit_author_address
'chaolai tong'
;Shanghai institute of Organic Chemistry,Chinese Academy of Sciences
China
;
_audit_update_record             
;
2022-01-14 deposited with the CCDC.	2022-07-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H11 F7 O3'
_chemical_formula_weight         372.24

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6131(4)
_cell_length_b                   8.0077(4)
_cell_length_c                   14.8609(7)
_cell_angle_alpha                101.045(2)
_cell_angle_beta                 94.103(2)
_cell_angle_gamma                118.1070(10)
_cell_volume                     770.51(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8086
_cell_measurement_theta_min      5.686
_cell_measurement_theta_max      55.080

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.165
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6121
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15172
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.843
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             2988
_reflns_number_gt                2474
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0564P)²+0.1679P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.047(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2988
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.1213
_refine_ls_wR_factor_gt          0.1122
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.46421(17) 0.92644(16) 0.90131(7) 0.0710(3) Uani 1 1 d . . . . .
F2 F 0.4229(2) 0.6092(2) 0.94756(9) 0.0989(5) Uani 1 1 d . . . . .
F3 F 0.7226(2) 0.8466(3) 1.00065(8) 0.1061(5) Uani 1 1 d . . . . .
F4 F 0.6655(2) 0.6110(2) 0.88482(9) 0.0899(4) Uani 1 1 d . . . . .
F5 F 0.8167(2) 1.15876(19) 0.91821(10) 0.1094(5) Uani 1 1 d . . . . .
F6 F 0.91333(17) 0.9673(2) 0.84923(9) 0.0885(4) Uani 1 1 d . . . . .
F7 F 0.7426(2) 1.05890(19) 0.76967(10) 0.0942(4) Uani 1 1 d . . . . .
O1 O 0.68753(18) 0.6891(2) 0.69910(9) 0.0739(4) Uani 1 1 d . . . . .
O2 O 0.39127(16) 0.51654(18) 0.60793(7) 0.0571(3) Uani 1 1 d . . . . .
O3 O -0.24453(18) 0.07362(19) 0.40811(9) 0.0693(4) Uani 1 1 d . . . . .
C1 C 0.5100(2) 0.6374(2) 0.69174(11) 0.0528(4) Uani 1 1 d . . . . .
C2 C 0.4128(2) 0.6886(2) 0.76497(10) 0.0483(4) Uani 1 1 d . . . . .
C3 C 0.2061(2) 0.6010(2) 0.75316(10) 0.0483(4) Uani 1 1 d . . . . .
C4 C 0.0868(2) 0.4681(2) 0.66374(10) 0.0475(4) Uani 1 1 d . . . . .
C5 C 0.1834(2) 0.4292(2) 0.59321(10) 0.0475(4) Uani 1 1 d . . . . .
C6 C 0.0835(2) 0.3017(2) 0.50663(11) 0.0526(4) Uani 1 1 d . . . . .
H6 H 0.1548 0.2807 0.4616 0.063 Uiso 1 1 calc R U . . .
C7 C -0.1263(2) 0.2059(2) 0.48880(12) 0.0560(4) Uani 1 1 d . . . . .
C8 C -0.2294(3) 0.2445(3) 0.55669(13) 0.0645(5) Uani 1 1 d . . . . .
H8 H -0.3702 0.1829 0.5438 0.077 Uiso 1 1 calc R U . . .
C9 C -0.1261(3) 0.3712(3) 0.64131(12) 0.0589(4) Uani 1 1 d . . . . .
H9 H -0.1980 0.3944 0.6855 0.071 Uiso 1 1 calc R U . . .
C10 C 0.0861(3) 0.6243(3) 0.82642(12) 0.0655(5) Uani 1 1 d . . . . .
H10A H 0.0292 0.7026 0.8119 0.098 Uiso 1 1 calc R U . . .
H10B H 0.1738 0.6873 0.8865 0.098 Uiso 1 1 calc R U . . .
H10C H -0.0211 0.4977 0.8274 0.098 Uiso 1 1 calc R U . . .
C11 C 0.5560(3) 0.8317(3) 0.85550(11) 0.0551(4) Uani 1 1 d . . . . .
C12 C 0.5940(3) 0.7238(3) 0.92322(13) 0.0721(5) Uani 1 1 d . . . . .
C13 C 0.7617(3) 1.0046(3) 0.84680(14) 0.0743(5) Uani 1 1 d . . . . .
C14 C -0.1491(3) 0.0138(3) 0.33941(12) 0.0614(4) Uani 1 1 d . . . . .
H14A H -0.0677 -0.0342 0.3665 0.074 Uiso 1 1 calc R U . . .
H14B H -0.0615 0.1234 0.3156 0.074 Uiso 1 1 calc R U . . .
C15 C -0.3144(3) -0.1457(3) 0.26228(14) 0.0769(6) Uani 1 1 d . . . . .
H15A H -0.2561 -0.1963 0.2170 0.115 Uiso 1 1 calc R U . . .
H15B H -0.3873 -0.0939 0.2330 0.115 Uiso 1 1 calc R U . . .
H15C H -0.4055 -0.2491 0.2875 0.115 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 C11 1.3770(18) . ?
F2 C12 1.319(3) . ?
F3 C12 1.322(2) . ?
F4 C12 1.322(2) . ?
F5 C13 1.332(2) . ?
F6 C13 1.321(2) . ?
F7 C13 1.323(3) . ?
O1 C1 1.2019(19) . ?
O2 C1 1.3630(19) . ?
O2 C5 1.3748(18) . ?
O3 C7 1.353(2) . ?
O3 C14 1.431(2) . ?
C1 C2 1.459(2) . ?
C2 C3 1.368(2) . ?
C2 C11 1.528(2) . ?
C3 C4 1.449(2) . ?
C3 C10 1.510(2) . ?
C4 C5 1.392(2) . ?
C4 C9 1.407(2) . ?
C5 C6 1.379(2) . ?
C6 C7 1.385(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.397(2) . ?
C8 C9 1.359(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.540(3) . ?
C11 C13 1.563(3) . ?
C14 C15 1.499(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
C1 O2 C5 122.17(12) . . ?
C7 O3 C14 118.26(13) . . ?
O1 C1 O2 116.05(13) . . ?
O1 C1 C2 125.65(14) . . ?
O2 C1 C2 118.28(13) . . ?
C3 C2 C1 120.66(14) . . ?
C3 C2 C11 123.73(13) . . ?
C1 C2 C11 115.46(13) . . ?
C2 C3 C4 118.46(13) . . ?
C2 C3 C10 126.06(15) . . ?
C4 C3 C10 115.45(14) . . ?
C5 C4 C9 115.73(15) . . ?
C5 C4 C3 119.76(13) . . ?
C9 C4 C3 124.51(14) . . ?
O2 C5 C6 115.44(13) . . ?
O2 C5 C4 120.35(14) . . ?
C6 C5 C4 124.19(14) . . ?
C5 C6 C7 117.89(14) . . ?
C5 C6 H6 121.1 . . ?
C7 C6 H6 121.1 . . ?
O3 C7 C6 124.52(15) . . ?
O3 C7 C8 115.64(14) . . ?
C6 C7 C8 119.84(15) . . ?
C9 C8 C7 120.70(15) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C4 121.61(15) . . ?
C8 C9 H9 119.2 . . ?
C4 C9 H9 119.2 . . ?
C3 C10 H10A 109.5 . . ?
C3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
F1 C11 C2 108.88(13) . . ?
F1 C11 C12 105.27(13) . . ?
C2 C11 C12 111.50(15) . . ?
F1 C11 C13 102.92(14) . . ?
C2 C11 C13 117.28(13) . . ?
C12 C11 C13 109.97(16) . . ?
F2 C12 F4 107.04(19) . . ?
F2 C12 F3 107.31(17) . . ?
F4 C12 F3 108.22(16) . . ?
F2 C12 C11 110.08(16) . . ?
F4 C12 C11 111.97(15) . . ?
F3 C12 C11 111.99(18) . . ?
F6 C13 F7 109.03(18) . . ?
F6 C13 F5 106.39(17) . . ?
F7 C13 F5 106.93(18) . . ?
F6 C13 C11 114.25(18) . . ?
F7 C13 C11 110.91(16) . . ?
F5 C13 C11 108.99(16) . . ?
O3 C14 C15 107.19(15) . . ?
O3 C14 H14A 110.3 . . ?
C15 C14 H14A 110.3 . . ?
O3 C14 H14B 110.3 . . ?
C15 C14 H14B 110.3 . . ?
H14A C14 H14B 108.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C5 O2 C1 O1 172.71(16) . . . . ?
C5 O2 C1 C2 -5.7(2) . . . . ?
O1 C1 C2 C3 -171.28(18) . . . . ?
O2 C1 C2 C3 6.9(2) . . . . ?
O1 C1 C2 C11 4.4(3) . . . . ?
O2 C1 C2 C11 -177.38(14) . . . . ?
C1 C2 C3 C4 -4.8(2) . . . . ?
C11 C2 C3 C4 179.90(14) . . . . ?
C1 C2 C3 C10 173.19(16) . . . . ?
C11 C2 C3 C10 -2.1(3) . . . . ?
C2 C3 C4 C5 1.4(2) . . . . ?
C10 C3 C4 C5 -176.76(15) . . . . ?
C2 C3 C4 C9 -178.64(15) . . . . ?
C10 C3 C4 C9 3.2(2) . . . . ?
C1 O2 C5 C6 -176.25(15) . . . . ?
C1 O2 C5 C4 2.4(2) . . . . ?
C9 C4 C5 O2 179.94(14) . . . . ?
C3 C4 C5 O2 -0.1(2) . . . . ?
C9 C4 C5 C6 -1.5(2) . . . . ?
C3 C4 C5 C6 178.42(14) . . . . ?
O2 C5 C6 C7 178.44(14) . . . . ?
C4 C5 C6 C7 -0.2(2) . . . . ?
C14 O3 C7 C6 6.2(3) . . . . ?
C14 O3 C7 C8 -174.09(16) . . . . ?
C5 C6 C7 O3 -178.40(15) . . . . ?
C5 C6 C7 C8 1.9(3) . . . . ?
O3 C7 C8 C9 178.35(17) . . . . ?
C6 C7 C8 C9 -1.9(3) . . . . ?
C7 C8 C9 C4 0.1(3) . . . . ?
C5 C4 C9 C8 1.5(3) . . . . ?
C3 C4 C9 C8 -178.43(16) . . . . ?
C3 C2 C11 F1 -28.5(2) . . . . ?
C1 C2 C11 F1 155.91(14) . . . . ?
C3 C2 C11 C12 87.17(19) . . . . ?
C1 C2 C11 C12 -88.38(18) . . . . ?
C3 C2 C11 C13 -144.79(17) . . . . ?
C1 C2 C11 C13 39.7(2) . . . . ?
F1 C11 C12 F2 55.3(2) . . . . ?
C2 C11 C12 F2 -62.62(19) . . . . ?
C13 C11 C12 F2 165.52(16) . . . . ?
F1 C11 C12 F4 174.23(16) . . . . ?
C2 C11 C12 F4 56.3(2) . . . . ?
C13 C11 C12 F4 -75.5(2) . . . . ?
F1 C11 C12 F3 -64.0(2) . . . . ?
C2 C11 C12 F3 178.08(15) . . . . ?
C13 C11 C12 F3 46.2(2) . . . . ?
F1 C11 C13 F6 148.09(15) . . . . ?
C2 C11 C13 F6 -92.45(19) . . . . ?
C12 C11 C13 F6 36.3(2) . . . . ?
F1 C11 C13 F7 -88.20(17) . . . . ?
C2 C11 C13 F7 31.3(2) . . . . ?
C12 C11 C13 F7 160.03(16) . . . . ?
F1 C11 C13 F5 29.3(2) . . . . ?
C2 C11 C13 F5 148.71(17) . . . . ?
C12 C11 C13 F5 -82.5(2) . . . . ?
C7 O3 C14 C15 174.55(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C14 H14B O1 0.97 2.57 3.357(2) 138.5 2_666

_refine_diff_density_max         0.211
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.030

_shelxl_version_number           2013-4

