# 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_201912122
_database_code_depnum_ccdc_archive 'CCDC 1966094'
loop_
_audit_author_name
_audit_author_address
'Shouxiong Chen'
;CHOF
China
;
_audit_update_record             
;
2019-12-12 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
_audit_creation_date             2019-12-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C13 H6 F6 O2'
_chemical_formula_sum            'C13 H6 F6 O2'
_chemical_formula_weight         308.18
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-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                   14.9423(17)
_cell_length_b                   14.9112(15)
_cell_length_c                   11.9436(12)
_cell_angle_alpha                90
_cell_angle_beta                 116.421(4)
_cell_angle_gamma                90
_cell_volume                     2383.2(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3920
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.015
_cell_measurement_theta_min      2.287
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5615
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1419 before and 0.0680 after correction.
The Ratio of minimum to maximum transmission is 0.7535.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.718
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15018
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.099
_diffrn_reflns_theta_min         2.287
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1571
_reflns_number_total             2130
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         2130
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0454
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0431P)²+3.8612P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1134
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F2 F 0.48256(12) 0.12161(11) 0.36526(15) 0.0501(5) Uani 1 1 d . . . . .
F3 F 0.32318(12) 0.11069(10) 0.26556(14) 0.0485(4) Uani 1 1 d . . . . .
O1 O 0.38311(13) 0.14069(11) 0.51117(15) 0.0329(4) Uani 1 1 d . . . . .
O2 O 0.38150(14) 0.49019(11) 0.42453(16) 0.0393(5) Uani 1 1 d . . . . .
F1 F 0.39653(14) 0.23084(10) 0.24896(14) 0.0514(5) Uani 1 1 d . . . . .
C6 C 0.37950(16) 0.32581(16) 0.5716(2) 0.0262(5) Uani 1 1 d . . . . .
F4 F 0.40331(16) 0.64666(11) 0.54096(19) 0.0693(6) Uani 1 1 d . . . . .
F6 F 0.3862(2) 0.58516(11) 0.69050(16) 0.0914(8) Uani 1 1 d . . . . .
C9 C 0.38623(18) 0.29537(16) 0.4608(2) 0.0292(5) Uani 1 1 d . . . . .
C10 C 0.37611(17) 0.16417(16) 0.6189(2) 0.0289(5) Uani 1 1 d . . . . .
C11 C 0.36846(17) 0.26879(17) 0.7657(2) 0.0291(6) Uani 1 1 d . . . . .
C12 C 0.37484(16) 0.25391(16) 0.6530(2) 0.0269(5) Uani 1 1 d . . . . .
C13 C 0.36185(19) 0.19826(17) 0.8363(2) 0.0338(6) Uani 1 1 d . . . . .
C14 C 0.37485(18) 0.48958(16) 0.5225(2) 0.0304(6) Uani 1 1 d . . . . .
F5 F 0.26123(16) 0.60080(13) 0.5156(2) 0.0832(7) Uani 1 1 d . . . . .
C16 C 0.38828(18) 0.20806(16) 0.4383(2) 0.0293(6) Uani 1 1 d . . . . .
C17 C 0.37604(18) 0.41425(16) 0.5991(2) 0.0298(6) Uani 1 1 d . . . . .
C18 C 0.3620(2) 0.10989(18) 0.7978(3) 0.0379(6) Uani 1 1 d . . . . .
C19 C 0.36948(19) 0.09247(18) 0.6894(2) 0.0342(6) Uani 1 1 d . . . . .
C20 C 0.3974(2) 0.16859(17) 0.3283(2) 0.0365(6) Uani 1 1 d . . . . .
C21 C 0.3582(2) 0.58118(17) 0.5695(2) 0.0398(7) Uani 1 1 d . . . . .
H17 H 0.3719(16) 0.4284(15) 0.672(2) 0.022(6) Uiso 1 1 d . . . . .
H13 H 0.3564(18) 0.2112(17) 0.912(2) 0.036(7) Uiso 1 1 d . . . . .
H9 H 0.389(2) 0.3364(19) 0.400(3) 0.045(8) Uiso 1 1 d . . . . .
H18 H 0.3576(19) 0.0588(19) 0.847(2) 0.042(7) Uiso 1 1 d . . . . .
H11 H 0.3671(19) 0.3302(18) 0.795(2) 0.040(7) Uiso 1 1 d . . . . .
H19 H 0.3723(19) 0.034(2) 0.662(2) 0.042(8) Uiso 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
F2 C20 1.343(3) . ?
F3 C20 1.341(3) . ?
O1 C10 1.381(3) . ?
O1 C16 1.354(3) . ?
O2 C14 1.218(3) . ?
F1 C20 1.322(3) . ?
C6 C9 1.444(3) . ?
C6 C12 1.470(3) . ?
C6 C17 1.366(3) . ?
F4 C21 1.315(3) . ?
F6 C21 1.315(3) . ?
C9 C16 1.332(3) . ?
C10 C12 1.401(3) . ?
C10 C19 1.392(3) . ?
C11 C12 1.408(3) . ?
C11 C13 1.379(3) . ?
C13 C18 1.396(4) . ?
C14 C17 1.444(3) . ?
C14 C21 1.538(3) . ?
F5 C21 1.330(3) . ?
C16 C20 1.501(3) . ?
C18 C19 1.373(4) . ?

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
C16 O1 C10 117.42(18) . . ?
C9 C6 C12 114.8(2) . . ?
C17 C6 C9 123.3(2) . . ?
C17 C6 C12 121.8(2) . . ?
C16 C9 C6 120.6(2) . . ?
O1 C10 C12 122.0(2) . . ?
O1 C10 C19 115.1(2) . . ?
C19 C10 C12 122.9(2) . . ?
C13 C11 C12 121.2(2) . . ?
C10 C12 C6 119.6(2) . . ?
C10 C12 C11 116.3(2) . . ?
C11 C12 C6 124.1(2) . . ?
C11 C13 C18 120.5(2) . . ?
O2 C14 C17 129.2(2) . . ?
O2 C14 C21 116.1(2) . . ?
C17 C14 C21 114.7(2) . . ?
O1 C16 C20 109.0(2) . . ?
C9 C16 O1 125.6(2) . . ?
C9 C16 C20 125.4(2) . . ?
C6 C17 C14 126.1(2) . . ?
C19 C18 C13 120.1(2) . . ?
C18 C19 C10 118.9(2) . . ?
F2 C20 C16 111.0(2) . . ?
F3 C20 F2 106.0(2) . . ?
F3 C20 C16 111.5(2) . . ?
F1 C20 F2 108.0(2) . . ?
F1 C20 F3 108.0(2) . . ?
F1 C20 C16 112.1(2) . . ?
F4 C21 C14 112.3(2) . . ?
F4 C21 F5 106.6(2) . . ?
F6 C21 F4 107.6(2) . . ?
F6 C21 C14 114.6(2) . . ?
F6 C21 F5 105.5(3) . . ?
F5 C21 C14 109.7(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_11
_database_code_depnum_ccdc_archive 'CCDC 2122313'
loop_
_audit_author_name
_audit_author_address
Chen
;Minjiang University
China
;
_audit_update_record             
;
2021-11-16 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
_audit_creation_date             2021-11-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H8 F3 N O4'
_chemical_formula_sum            'C11 H8 F3 N O4'
_chemical_formula_weight         275.18
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   6.9523(6)
_cell_length_b                   17.6379(13)
_cell_length_c                   18.5809(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2278.5(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3938
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.631
_cell_measurement_theta_min      2.557
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.956
_exptl_absorpt_coefficient_mu    0.153
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5860
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1592 before and 0.0781 after correction.
The Ratio of minimum to maximum transmission is 0.7864.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1120
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0838
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            20651
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.023
_diffrn_reflns_theta_max         25.023
_diffrn_reflns_theta_min         2.309
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1514
_reflns_number_total             2019
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       lb20201022
_computing_data_collection       ?
_computing_data_reduction        lb20201022
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2019
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0512
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0731P)²+0.9188P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1377
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00C(H00C), C00E(H00E), C00G(H00G)
2.b Idealised Me refined as rotating group:
 C00J(H00A,H00D,H00F)
2.c Idealised tetrahedral OH refined as rotating group:
 O005(H005)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F001 F 0.4740(2) 0.55608(9) 0.58025(9) 0.0446(5) Uani 1 1 d . . . . .
F002 F 0.6367(3) 0.65053(8) 0.62218(9) 0.0472(5) Uani 1 1 d . . . . .
O003 O 0.7360(2) 0.51898(8) 0.68260(8) 0.0248(4) Uani 1 1 d . . . . .
F004 F 0.6917(2) 0.60977(9) 0.51509(8) 0.0475(5) Uani 1 1 d . . . . .
O005 O 0.9801(2) 0.56898(9) 0.61165(9) 0.0294(5) Uani 1 1 d . . . . .
H005 H 0.973794 0.607719 0.635932 0.044 Uiso 1 1 calc GR . . . .
O006 O 0.9865(3) 0.19760(10) 0.78721(11) 0.0445(5) Uani 1 1 d . . . . .
N1 N 0.9194(3) 0.25070(12) 0.82183(13) 0.0352(6) Uani 1 1 d . . . . .
O7 O 0.8923(4) 0.24766(12) 0.88650(12) 0.0665(8) Uani 1 1 d . . . . .
C009 C 0.7868(3) 0.45184(12) 0.71429(12) 0.0187(5) Uani 1 1 d . . . . .
C00A C 0.8325(3) 0.38808(12) 0.67309(12) 0.0201(5) Uani 1 1 d . . . . .
C00B C 0.7824(3) 0.45055(13) 0.78875(12) 0.0221(5) Uani 1 1 d . . . . .
H00B H 0.750795 0.494007 0.814507 0.026 Uiso 1 1 calc R . . . .
C00C C 0.8773(3) 0.32159(13) 0.70952(13) 0.0221(5) Uani 1 1 d . . . . .
H00C H 0.909874 0.278020 0.684110 0.027 Uiso 1 1 calc R . . . .
C00D C 0.8729(3) 0.32082(13) 0.78389(13) 0.0248(6) Uani 1 1 d . . . . .
C00E C 0.8251(3) 0.38430(14) 0.82411(13) 0.0266(6) Uani 1 1 d . . . . .
H00E H 0.822088 0.382048 0.874104 0.032 Uiso 1 1 calc R . . . .
C00F C 0.8332(3) 0.39485(13) 0.59422(13) 0.0242(6) Uani 1 1 d . . . . .
C00G C 0.8142(4) 0.46356(13) 0.56578(13) 0.0276(6) Uani 1 1 d . . . . .
H00G H 0.809373 0.468369 0.515968 0.033 Uiso 1 1 calc R . . . .
C00H C 0.8003(4) 0.53316(13) 0.61091(13) 0.0249(6) Uani 1 1 d . . . . .
C00I C 0.6474(4) 0.58745(15) 0.58234(14) 0.0334(6) Uani 1 1 d . . . . .
C00J C 0.8580(4) 0.32531(14) 0.54903(14) 0.0385(7) Uani 1 1 d . . . . .
H00A H 0.981646 0.303223 0.558456 0.058 Uiso 1 1 calc GR . . . .
H00D H 0.849218 0.338723 0.499063 0.058 Uiso 1 1 calc GR . . . .
H00F H 0.758987 0.289362 0.560569 0.058 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F001 C00I 1.327(3) . ?
F002 C00I 1.338(3) . ?
O003 C009 1.369(3) . ?
O003 C00H 1.427(3) . ?
F004 C00I 1.346(3) . ?
O005 H005 0.8200 . ?
O005 C00H 1.401(3) . ?
O006 N1 1.228(3) . ?
N1 O7 1.218(3) . ?
N1 C00D 1.460(3) . ?
C009 C00A 1.397(3) . ?
C009 C00B 1.384(3) . ?
C00A C00C 1.389(3) . ?
C00A C00F 1.470(3) . ?
C00B H00B 0.9300 . ?
C00B C00E 1.373(3) . ?
C00C H00C 0.9300 . ?
C00C C00D 1.382(3) . ?
C00D C00E 1.386(3) . ?
C00E H00E 0.9300 . ?
C00F C00G 1.329(3) . ?
C00F C00J 1.496(3) . ?
C00G H00G 0.9300 . ?
C00G C00H 1.490(3) . ?
C00H C00I 1.526(4) . ?
C00J H00A 0.9600 . ?
C00J H00D 0.9600 . ?
C00J H00F 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
C009 O003 C00H 118.19(17) . . ?
C00H O005 H005 109.5 . . ?
O006 N1 C00D 118.5(2) . . ?
O7 N1 O006 122.8(2) . . ?
O7 N1 C00D 118.7(2) . . ?
O003 C009 C00A 121.3(2) . . ?
O003 C009 C00B 116.00(19) . . ?
C00B C009 C00A 122.7(2) . . ?
C009 C00A C00F 118.8(2) . . ?
C00C C00A C009 117.6(2) . . ?
C00C C00A C00F 123.6(2) . . ?
C009 C00B H00B 120.4 . . ?
C00E C00B C009 119.2(2) . . ?
C00E C00B H00B 120.4 . . ?
C00A C00C H00C 120.3 . . ?
C00D C00C C00A 119.4(2) . . ?
C00D C00C H00C 120.3 . . ?
C00C C00D N1 119.1(2) . . ?
C00C C00D C00E 122.4(2) . . ?
C00E C00D N1 118.5(2) . . ?
C00B C00E C00D 118.8(2) . . ?
C00B C00E H00E 120.6 . . ?
C00D C00E H00E 120.6 . . ?
C00A C00F C00J 119.5(2) . . ?
C00G C00F C00A 118.0(2) . . ?
C00G C00F C00J 122.4(2) . . ?
C00F C00G H00G 118.9 . . ?
C00F C00G C00H 122.3(2) . . ?
C00H C00G H00G 118.9 . . ?
O003 C00H C00G 113.66(19) . . ?
O003 C00H C00I 102.51(19) . . ?
O005 C00H O003 110.44(18) . . ?
O005 C00H C00G 108.6(2) . . ?
O005 C00H C00I 110.01(19) . . ?
C00G C00H C00I 111.5(2) . . ?
F001 C00I F002 108.2(2) . . ?
F001 C00I F004 107.6(2) . . ?
F001 C00I C00H 112.4(2) . . ?
F002 C00I F004 106.4(2) . . ?
F002 C00I C00H 111.6(2) . . ?
F004 C00I C00H 110.3(2) . . ?
C00F C00J H00A 109.5 . . ?
C00F C00J H00D 109.5 . . ?
C00F C00J H00F 109.5 . . ?
H00A C00J H00D 109.5 . . ?
H00A C00J H00F 109.5 . . ?
H00D C00J H00F 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
O003 C009 C00A C00C -178.22(19) . . . . ?
O003 C009 C00A C00F 2.6(3) . . . . ?
O003 C009 C00B C00E 177.8(2) . . . . ?
O003 C00H C00I F001 -62.8(2) . . . . ?
O003 C00H C00I F002 59.0(2) . . . . ?
O003 C00H C00I F004 177.10(18) . . . . ?
O005 C00H C00I F001 179.73(19) . . . . ?
O005 C00H C00I F002 -58.5(3) . . . . ?
O005 C00H C00I F004 59.6(3) . . . . ?
O006 N1 C00D C00C 9.9(3) . . . . ?
O006 N1 C00D C00E -170.3(2) . . . . ?
N1 C00D C00E C00B 179.6(2) . . . . ?
O7 N1 C00D C00C -171.0(2) . . . . ?
O7 N1 C00D C00E 8.8(4) . . . . ?
C009 O003 C00H O005 -89.3(2) . . . . ?
C009 O003 C00H C00G 33.0(3) . . . . ?
C009 O003 C00H C00I 153.48(19) . . . . ?
C009 C00A C00C C00D 0.7(3) . . . . ?
C009 C00A C00F C00G 8.3(3) . . . . ?
C009 C00A C00F C00J -172.6(2) . . . . ?
C009 C00B C00E C00D 0.5(3) . . . . ?
C00A C009 C00B C00E 0.3(3) . . . . ?
C00A C00C C00D N1 179.8(2) . . . . ?
C00A C00C C00D C00E 0.0(3) . . . . ?
C00A C00F C00G C00H 2.5(4) . . . . ?
C00B C009 C00A C00C -0.9(3) . . . . ?
C00B C009 C00A C00F 179.9(2) . . . . ?
C00C C00A C00F C00G -170.8(2) . . . . ?
C00C C00A C00F C00J 8.2(3) . . . . ?
C00C C00D C00E C00B -0.6(3) . . . . ?
C00F C00A C00C C00D 179.9(2) . . . . ?
C00F C00G C00H O003 -22.7(3) . . . . ?
C00F C00G C00H O005 100.7(3) . . . . ?
C00F C00G C00H C00I -138.0(2) . . . . ?
C00G C00H C00I F001 59.2(3) . . . . ?
C00G C00H C00I F002 -179.1(2) . . . . ?
C00G C00H C00I F004 -61.0(3) . . . . ?
C00H O003 C009 C00A -24.2(3) . . . . ?
C00H O003 C009 C00B 158.27(19) . . . . ?
C00J C00F C00G C00H -176.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
