# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_123_sq
_database_code_depnum_ccdc_archive 'CCDC 2013786'
loop_
_audit_author_name
_audit_author_address
HEXAFLUOROACETYLACETONE-V-two
;Fuzhou University
China
;
_audit_update_record             
;
2020-07-03 deposited with the CCDC.	2020-10-02 downloaded from the CCDC.
;
_audit_creation_date             2020-07-01
_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         'C15 H9 F9 N2 O2'
_chemical_formula_sum            'C15 H9 F9 N2 O2'
_chemical_formula_weight         420.24
_chemical_absolute_configuration syn
_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           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   11.1311(12)
_cell_length_b                   25.229(3)
_cell_length_c                   13.9728(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3923.9(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3579
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.543
_cell_measurement_theta_min      2.475
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.0676 before and 0.0367 after correction.
The Ratio of minimum to maximum transmission is 0.9281.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11913
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.579
_diffrn_reflns_theta_min         2.000
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.989
_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         0.777
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                2900
_reflns_number_total             4458
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 1035 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4458
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0375
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0615P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1108
_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:
 C10(H10), C4(H4), C7(H7), C6(H6), C3(H3)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F5 F 0.6115(3) 0.34933(8) 0.17872(16) 0.0883(7) Uani 1 1 d . . . . .
N2 N 0.6563(2) 0.17299(10) 0.06745(16) 0.0471(6) Uani 1 1 d . . . . .
F4 F 0.4559(2) 0.31732(8) 0.11085(16) 0.0791(6) Uani 1 1 d . . . . .
N1 N 0.7250(2) 0.16244(9) 0.14116(16) 0.0481(6) Uani 1 1 d . . . . .
F1 F 0.7732(2) 0.13641(8) 0.34442(13) 0.0699(6) Uani 1 1 d . . . . .
C9 C 0.7533(2) 0.20007(11) 0.21828(19) 0.0439(6) Uani 1 1 d . . . . .
C12 C 0.6054(3) 0.21886(11) 0.05546(18) 0.0438(6) Uani 1 1 d . . . . .
F2 F 0.7163(2) 0.21420(9) 0.38321(13) 0.0763(6) Uani 1 1 d . . . . .
O2 O 0.4747(2) 0.25948(10) -0.05574(17) 0.0731(7) Uani 1 1 d . . . . .
F6 F 0.6098(2) 0.33836(7) 0.02736(14) 0.0795(6) Uani 1 1 d . . . . .
F3 F 0.59690(18) 0.16238(10) 0.30956(16) 0.0852(7) Uani 1 1 d . . . . .
O1 O 0.87624(18) 0.20624(10) 0.23190(16) 0.0609(6) Uani 1 1 d . . . . .
H1 H 0.906349 0.218980 0.183524 0.091 Uiso 1 1 calc GR . . . .
C11 C 0.6259(3) 0.26169(11) 0.12296(19) 0.0450(6) Uani 1 1 d . . . . .
C10 C 0.6925(3) 0.25166(12) 0.1994(2) 0.0497(7) Uani 1 1 d . . . . .
H10 H 0.701885 0.278576 0.244295 0.060 Uiso 1 1 calc R . . . .
F9 F 0.6153(3) 0.15470(13) -0.12790(19) 0.1295(13) Uani 1 1 d . . . . .
C14 C 0.5291(3) 0.22142(13) -0.0288(2) 0.0543(8) Uani 1 1 d . . . . .
C5 C 0.7679(3) 0.10815(13) 0.1423(2) 0.0600(9) Uani 1 1 d . . . . .
C13 C 0.5760(3) 0.31704(13) 0.1096(2) 0.0601(9) Uani 1 1 d . . . . .
C8 C 0.7104(3) 0.17712(13) 0.3149(2) 0.0530(8) Uani 1 1 d . . . . .
F8 F 0.4343(3) 0.17871(11) -0.15716(19) 0.1308(12) Uani 1 1 d . . . . .
F7 F 0.4699(3) 0.13040(11) -0.0349(3) 0.1278(12) Uani 1 1 d . . . . .
C4 C 0.8900(4) 0.09756(17) 0.1433(3) 0.0880(12) Uani 1 1 d . . . . .
H4 H 0.947096 0.124461 0.145245 0.106 Uiso 1 1 calc R . . . .
C15 C 0.5143(5) 0.17056(18) -0.0881(3) 0.0866(13) Uani 1 1 d . . . . .
C2 C 0.8410(7) 0.0029(2) 0.1361(3) 0.112(2) Uani 1 1 d . . . . .
C7 C 0.7238(6) 0.01583(17) 0.1342(5) 0.121(2) Uani 1 1 d . . . . .
H7 H 0.667066 -0.011096 0.129808 0.145 Uiso 1 1 calc R . . . .
C1 C 0.8836(8) -0.0542(2) 0.1316(5) 0.173(4) Uani 1 1 d . . . . .
H1A H 0.853769 -0.073197 0.186228 0.259 Uiso 1 1 calc GR . . . .
H1B H 0.969802 -0.055022 0.131761 0.259 Uiso 1 1 calc GR . . . .
H1C H 0.854134 -0.070464 0.074142 0.259 Uiso 1 1 calc GR . . . .
C6 C 0.6842(4) 0.06867(16) 0.1387(4) 0.0918(14) Uani 1 1 d . . . . .
H6 H 0.602638 0.076572 0.139235 0.110 Uiso 1 1 calc R . . . .
C3 C 0.9229(6) 0.0433(2) 0.1412(4) 0.122(2) Uani 1 1 d . . . . .
H3 H 1.004056 0.034660 0.143506 0.147 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F5 C13 1.324(4) . ?
N2 N1 1.310(3) . ?
N2 C12 1.300(4) . ?
F4 C13 1.337(4) . ?
N1 C9 1.470(4) . ?
N1 C5 1.451(4) . ?
F1 C8 1.309(4) . ?
C9 O1 1.391(3) . ?
C9 C10 1.491(4) . ?
C9 C8 1.545(4) . ?
C12 C11 1.452(4) . ?
C12 C14 1.453(4) . ?
F2 C8 1.338(4) . ?
O2 C14 1.196(4) . ?
F6 C13 1.323(4) . ?
F3 C8 1.319(4) . ?
C11 C10 1.325(4) . ?
C11 C13 1.515(4) . ?
F9 C15 1.316(6) . ?
C14 C15 1.537(5) . ?
C5 C4 1.385(6) . ?
C5 C6 1.365(6) . ?
F8 C15 1.329(4) . ?
F7 C15 1.351(6) . ?
C4 C3 1.418(7) . ?
C2 C7 1.344(9) . ?
C2 C1 1.517(7) . ?
C2 C3 1.369(9) . ?
C7 C6 1.405(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
C12 N2 N1 122.5(2) . . ?
N2 N1 C9 124.8(2) . . ?
N2 N1 C5 113.1(2) . . ?
C5 N1 C9 122.1(2) . . ?
N1 C9 C10 109.7(2) . . ?
N1 C9 C8 109.4(2) . . ?
O1 C9 N1 112.5(2) . . ?
O1 C9 C10 111.9(2) . . ?
O1 C9 C8 103.1(2) . . ?
C10 C9 C8 110.0(2) . . ?
N2 C12 C11 120.7(2) . . ?
N2 C12 C14 113.5(3) . . ?
C11 C12 C14 125.8(2) . . ?
C12 C11 C13 123.2(3) . . ?
C10 C11 C12 118.0(2) . . ?
C10 C11 C13 118.7(3) . . ?
C11 C10 C9 124.3(3) . . ?
C12 C14 C15 117.6(3) . . ?
O2 C14 C12 125.9(3) . . ?
O2 C14 C15 116.5(3) . . ?
C4 C5 N1 120.4(3) . . ?
C6 C5 N1 117.6(3) . . ?
C6 C5 C4 122.0(4) . . ?
F5 C13 F4 106.6(3) . . ?
F5 C13 C11 111.6(3) . . ?
F4 C13 C11 111.7(3) . . ?
F6 C13 F5 107.4(3) . . ?
F6 C13 F4 107.1(3) . . ?
F6 C13 C11 112.2(3) . . ?
F1 C8 C9 113.9(3) . . ?
F1 C8 F2 107.3(2) . . ?
F1 C8 F3 107.9(3) . . ?
F2 C8 C9 110.2(3) . . ?
F3 C8 C9 110.6(2) . . ?
F3 C8 F2 106.6(3) . . ?
C5 C4 C3 116.0(5) . . ?
F9 C15 C14 113.0(4) . . ?
F9 C15 F8 108.2(4) . . ?
F9 C15 F7 108.5(4) . . ?
F8 C15 C14 109.5(3) . . ?
F8 C15 F7 105.7(4) . . ?
F7 C15 C14 111.6(3) . . ?
C7 C2 C1 122.2(7) . . ?
C7 C2 C3 117.8(5) . . ?
C3 C2 C1 120.0(7) . . ?
C2 C7 C6 122.3(6) . . ?
C5 C6 C7 118.7(5) . . ?
C2 C3 C4 123.3(6) . . ?

_platon_squeeze_details          ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.500 -0.004 388 97 ' '
2 0.500 0.000 -0.011 388 97 ' '

_platon_squeeze_void_probe_radius 1.20
_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_exp_10432
_database_code_depnum_ccdc_archive 'CCDC 2013787'
loop_
_audit_author_name
_audit_author_address
HEXAFLUOROACETYLACETONE-V-seven
;Fuzhou University
China
;
_audit_update_record             
;
2020-07-03 deposited with the CCDC.	2020-10-02 downloaded from the CCDC.
;
_audit_creation_date             2020-07-01
_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         'C13 H5 Cl F9 N3 O2'
_chemical_formula_sum            'C13 H5 Cl F9 N3 O2'
_chemical_formula_weight         441.65
_chemical_absolute_configuration syn
_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 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   14.7807(17)
_cell_length_b                   15.297(2)
_cell_length_c                   7.5433(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1705.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    652
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      48.8800
_cell_measurement_theta_min      4.1340
_shelx_estimated_absorpt_T_max   0.730
_shelx_estimated_absorpt_T_min   0.657
_exptl_absorpt_coefficient_mu    3.054
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.720
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0769
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            4010
_diffrn_reflns_point_group_measured_fraction_full 0.687
_diffrn_reflns_point_group_measured_fraction_max 0.671
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.439
_diffrn_reflns_theta_min         4.159
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1281
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      0.00  34.00   1.00    1.00    --  -33.50  57.00  30.00   34
  2  ω    -50.00 -13.00   1.00    1.00    --  -33.50  57.00  30.00   37
  3  ω      6.00  34.00   1.00    1.00    --  -33.50  57.00  60.00   28
  4  ω     12.00  58.00   1.00    1.00    --   36.37 -99.00-180.00   46
  5  ω     19.00  44.00   1.00    1.00    --   36.37  77.00 -90.00   25
  6  ω     47.00  94.00   1.00    1.00    --   36.37  77.00 -90.00   47
  7  ω     47.00 104.00   1.00    1.00    --  108.00 -61.00 -90.00   57
  8  ω     40.00  66.00   1.00    1.00    --  108.00 -45.00 -90.00   26
  9  ω     48.00 109.00   1.00    1.00    --  108.00 -94.00 120.00   61
 10  ω     92.00 121.00   1.00    1.00    --  108.00 -45.00 -90.00   29
 11  ω     39.00  88.00   1.00    1.00    --  108.00 -94.00-150.00   49
 12  ω     76.00 176.00   1.00    1.00    --  108.00  15.00 -90.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0583163000
_diffrn_orient_matrix_UB_12      0.0817849000
_diffrn_orient_matrix_UB_13      -0.0338795000
_diffrn_orient_matrix_UB_21      -0.0831095000
_diffrn_orient_matrix_UB_22      0.0586755000
_diffrn_orient_matrix_UB_23      0.0322836000
_diffrn_orient_matrix_UB_31      0.0233872000
_diffrn_orient_matrix_UB_32      0.0043718000
_diffrn_orient_matrix_UB_33      0.1987939000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.254
_reflns_Friedel_fraction_full    0.317
_reflns_Friedel_fraction_max     0.295
_reflns_number_gt                1237
_reflns_number_total             2219
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 
;
 Flack x determined using 211 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.15(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         2219
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1106
_refine_ls_R_factor_gt           0.0538
_refine_ls_restrained_S_all      1.015
_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)+(0.0346P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.1219
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C5(H5), C8(H8)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.69758(9) 0.14735(11) 0.1428(3) 0.0921(5) Uani 1 1 d . . . . .
F1 F 0.4911(2) 0.5448(2) 0.4301(7) 0.1419(19) Uani 1 1 d . . . . .
F2 F 0.3922(3) 0.5426(2) 0.2304(5) 0.1242(16) Uani 1 1 d . . . . .
F3 F 0.4070(2) 0.65581(19) 0.3869(6) 0.1186(16) Uani 1 1 d . . . . .
F4 F 0.1335(2) 0.5090(2) 0.5536(5) 0.0992(13) Uani 1 1 d . . . . .
F5 F 0.0932(2) 0.4030(2) 0.7245(6) 0.1065(15) Uani 1 1 d . . . . .
F6 F 0.1782(2) 0.50264(19) 0.8234(5) 0.0933(12) Uani 1 1 d . . . . .
F7 F 0.3066(2) 0.1806(2) 0.8403(5) 0.1060(13) Uani 1 1 d . . . . .
F8 F 0.4130(2) 0.2753(3) 0.8063(5) 0.1361(16) Uani 1 1 d . . . . .
F9 F 0.4187(2) 0.1515(2) 0.6736(6) 0.1201(14) Uani 1 1 d . . . . .
N1 N 0.6111(2) 0.2578(3) 0.3366(6) 0.0586(13) Uani 1 1 d . . . . .
N2 N 0.3806(2) 0.3946(2) 0.4531(6) 0.0515(12) Uani 1 1 d . . . . .
O1 O 0.2994(3) 0.5890(2) 0.6126(6) 0.0920(15) Uani 1 1 d . . . . .
O2 O 0.2759(2) 0.18582(18) 0.4737(5) 0.0643(12) Uani 1 1 d . . . . .
H2 H 0.226961 0.199962 0.431422 0.096 Uiso 1 1 calc GR . . . .
C1 C 0.5998(3) 0.1915(3) 0.2270(8) 0.0635(17) Uani 1 1 d . . . . .
C2 C 0.5157(3) 0.1595(3) 0.1794(8) 0.0689(18) Uani 1 1 d . . . . .
H2A H 0.510379 0.113183 0.100250 0.083 Uiso 1 1 calc R . . . .
C3 C 0.4398(3) 0.1979(3) 0.2521(8) 0.0671(18) Uani 1 1 d . . . . .
H3 H 0.382258 0.179246 0.219915 0.081 Uiso 1 1 calc R . . . .
C4 C 0.4509(3) 0.2646(3) 0.3737(7) 0.0509(14) Uani 1 1 d . . . . .
C5 C 0.5374(3) 0.2938(3) 0.4094(7) 0.0542(15) Uani 1 1 d . . . . .
H5 H 0.544802 0.340448 0.487200 0.065 Uiso 1 1 calc R . . . .
N3 N 0.3765(2) 0.3065(2) 0.4559(6) 0.0509(12) Uani 1 1 d . . . . .
C7 C 0.3119(3) 0.2558(3) 0.5679(7) 0.0560(15) Uani 1 1 d . . . . .
C8 C 0.2403(3) 0.3155(3) 0.6370(7) 0.0557(15) Uani 1 1 d . . . . .
H8 H 0.190537 0.290627 0.692953 0.067 Uiso 1 1 calc R . . . .
C9 C 0.2433(3) 0.4023(3) 0.6234(7) 0.0504(14) Uani 1 1 d . . . . .
C10 C 0.3195(3) 0.4415(3) 0.5329(8) 0.0536(15) Uani 1 1 d . . . . .
C11 C 0.3372(3) 0.5369(3) 0.5247(8) 0.0621(17) Uani 1 1 d . . . . .
C12 C 0.4080(4) 0.5676(3) 0.3927(10) 0.089(2) Uani 1 1 d . . . . .
C13 C 0.1631(4) 0.4537(3) 0.6776(9) 0.080(2) Uani 1 1 d . . . . .
C14 C 0.3638(3) 0.2149(4) 0.7256(9) 0.082(2) 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
Cl1 C1 1.717(5) . ?
F1 C12 1.307(6) . ?
F2 C12 1.304(8) . ?
F3 C12 1.350(5) . ?
F4 C13 1.334(7) . ?
F5 C13 1.339(6) . ?
F6 C13 1.349(7) . ?
F7 C14 1.319(6) . ?
F8 C14 1.324(7) . ?
F9 C14 1.324(6) . ?
N1 C1 1.319(6) . ?
N1 C5 1.338(6) . ?
N2 N3 1.349(5) . ?
N2 C10 1.301(6) . ?
O1 C11 1.178(6) . ?
O2 C7 1.391(6) . ?
C1 C2 1.384(6) . ?
C2 C3 1.379(7) . ?
C3 C4 1.381(7) . ?
C4 C5 1.381(6) . ?
C4 N3 1.416(6) . ?
N3 C7 1.492(6) . ?
C7 C8 1.492(6) . ?
C7 C14 1.547(8) . ?
C8 C9 1.333(6) . ?
C9 C10 1.447(6) . ?
C9 C13 1.480(7) . ?
C10 C11 1.483(6) . ?
C11 C12 1.519(8) . ?

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 C5 118.1(4) . . ?
C10 N2 N3 120.9(4) . . ?
N1 C1 Cl1 115.3(4) . . ?
N1 C1 C2 123.2(5) . . ?
C2 C1 Cl1 121.4(4) . . ?
C3 C2 C1 118.5(5) . . ?
C2 C3 C4 118.8(5) . . ?
C3 C4 N3 122.2(4) . . ?
C5 C4 C3 118.6(5) . . ?
C5 C4 N3 119.2(4) . . ?
N1 C5 C4 122.7(4) . . ?
N2 N3 C4 114.2(4) . . ?
N2 N3 C7 123.8(4) . . ?
C4 N3 C7 120.7(4) . . ?
O2 C7 N3 110.8(4) . . ?
O2 C7 C8 112.2(4) . . ?
O2 C7 C14 105.7(4) . . ?
N3 C7 C8 109.5(4) . . ?
N3 C7 C14 109.2(4) . . ?
C8 C7 C14 109.3(5) . . ?
C9 C8 C7 124.0(4) . . ?
C8 C9 C10 118.4(4) . . ?
C8 C9 C13 118.8(4) . . ?
C10 C9 C13 122.3(4) . . ?
N2 C10 C9 122.0(4) . . ?
N2 C10 C11 113.6(4) . . ?
C9 C10 C11 124.4(4) . . ?
O1 C11 C10 123.9(5) . . ?
O1 C11 C12 119.1(5) . . ?
C10 C11 C12 117.0(5) . . ?
F1 C12 F3 106.5(4) . . ?
F1 C12 C11 115.1(6) . . ?
F2 C12 F1 107.0(6) . . ?
F2 C12 F3 105.1(6) . . ?
F2 C12 C11 113.7(5) . . ?
F3 C12 C11 108.8(5) . . ?
F4 C13 F5 107.4(5) . . ?
F4 C13 F6 105.9(4) . . ?
F4 C13 C9 113.9(5) . . ?
F5 C13 F6 103.5(5) . . ?
F5 C13 C9 112.5(4) . . ?
F6 C13 C9 112.8(5) . . ?
F7 C14 F8 109.2(5) . . ?
F7 C14 F9 107.2(5) . . ?
F7 C14 C7 110.3(4) . . ?
F8 C14 F9 108.2(4) . . ?
F8 C14 C7 110.1(5) . . ?
F9 C14 C7 111.9(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.751
_oxdiff_exptl_absorpt_empirical_full_min 0.634
####################################################################### 
# 
# 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_1a
_database_code_depnum_ccdc_archive 'CCDC 2032426'
loop_
_audit_author_name
_audit_author_address
Pyridazine-w
;Fuzhou University
China
;
_audit_update_record             
;
2020-09-17 deposited with the CCDC.	2020-10-02 downloaded from the CCDC.
;
_audit_creation_date             2020-09-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H21 F9 N2 O2'
_chemical_formula_sum            'C25 H21 F9 N2 O2'
_chemical_formula_weight         552.44
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.2442(6)
_cell_length_b                   11.5216(7)
_cell_length_c                   12.9048(8)
_cell_angle_alpha                73.201(2)
_cell_angle_beta                 71.124(2)
_cell_angle_gamma                89.954(2)
_cell_volume                     1238.51(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9664
_cell_measurement_temperature    150
_cell_measurement_theta_max      25.035
_cell_measurement_theta_min      2.404
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1648 before and 0.0785 after correction.
The Ratio of minimum to maximum transmission is 0.8289.
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    1.481
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            38453
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.341
_diffrn_ambient_temperature      150
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3811
_reflns_number_total             4380
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         4380
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0377
_refine_ls_restrained_S_all      1.036
_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)+(0.0531P)²+0.4212P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0959
_refine_ls_wR_factor_ref         0.0998
_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:
 C00I(H00I), C00K(H00K), C00M(H00M), C00N(H00N), C00V(H00V), C00Y(H00Y),
 C010(H010), C011(H011)
2.b Idealised Me refined as rotating group:
 C00U(H00A,H00B,H00C), C00X(H00D,H00E,H00F), C00Z(H00G,H00H,H00J), C012(H01A,
 H01B,H01C)
2.c Idealised tetrahedral OH refined as rotating group:
 O009(H009)
;
_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 0.87216(10) 0.92294(8) -0.01590(8) 0.0319(2) Uani 1 1 d . . . . .
F002 F 0.99125(10) 0.82709(8) 0.09620(8) 0.0319(2) Uani 1 1 d . . . . .
F003 F 0.76748(11) 0.72172(9) 0.47615(8) 0.0363(2) Uani 1 1 d . . . . .
F004 F 0.81729(11) 0.94015(8) 0.15365(9) 0.0364(2) Uani 1 1 d . . . . .
F005 F 0.64205(11) 0.54622(9) 0.51926(8) 0.0371(2) Uani 1 1 d . . . . .
F006 F 0.88616(12) 0.56194(10) 0.47928(9) 0.0410(3) Uani 1 1 d . . . . .
F007 F 0.34758(11) 0.89621(10) 0.06704(8) 0.0393(3) Uani 1 1 d . . . . .
F008 F 0.30567(13) 0.98193(10) 0.19917(10) 0.0451(3) Uani 1 1 d . . . . .
O009 O 0.81677(13) 0.37624(10) -0.06736(9) 0.0295(3) Uani 1 1 d . . . . .
H009 H 0.897502 0.393449 -0.125021 0.044 Uiso 1 1 calc R U . . .
F00A F 0.20102(11) 0.80121(11) 0.23816(10) 0.0482(3) Uani 1 1 d . . . . .
O00B O 0.90956(12) 0.59672(10) 0.26932(10) 0.0307(3) Uani 1 1 d . . . . .
N00C N 0.57411(14) 0.73211(11) 0.34879(11) 0.0233(3) Uani 1 1 d . . . . .
N00D N 0.46459(14) 0.79340(12) 0.31809(11) 0.0267(3) Uani 1 1 d . . . . .
C00E C 0.76691(16) 0.65226(13) 0.08507(12) 0.0202(3) Uani 1 1 d . . . . .
C00F C 0.69147(16) 0.44461(13) 0.09408(13) 0.0210(3) Uani 1 1 d . . . . .
C00G C 0.80123(17) 0.46662(14) -0.01615(13) 0.0216(3) Uani 1 1 d . . . . .
C00H C 0.69194(16) 0.70828(13) 0.27263(13) 0.0217(3) Uani 1 1 d . . . . .
C00I C 0.89185(17) 0.57647(14) -0.07225(13) 0.0241(3) Uani 1 1 d . . . . .
H00I H 0.966143 0.588402 -0.146251 0.029 Uiso 1 1 calc R U . . .
C00J C 0.79921(17) 0.63756(14) 0.32206(13) 0.0233(3) Uani 1 1 d . . . . .
C00K C 0.67721(16) 0.54108(13) 0.14046(12) 0.0216(3) Uani 1 1 d . . . . .
H00K H 0.602058 0.530156 0.213937 0.026 Uiso 1 1 calc R U . . .
C00L C 0.46789(17) 0.82401(13) 0.20371(13) 0.0237(3) Uani 1 1 d . . . . .
C00M C 0.58647(17) 0.80524(13) 0.12164(13) 0.0226(3) Uani 1 1 d . . . . .
H00M H 0.582132 0.825183 0.046012 0.027 Uiso 1 1 calc R U . . .
C00N C 0.87644(17) 0.66963(14) -0.02262(13) 0.0227(3) Uani 1 1 d . . . . .
H00N H 0.940117 0.744504 -0.061858 0.027 Uiso 1 1 calc R U . . .
C00O C 0.72827(16) 0.75367(13) 0.14242(13) 0.0213(3) Uani 1 1 d . . . . .
C00P C 0.34873(17) 0.82425(14) 0.40967(13) 0.0251(3) Uani 1 1 d . . . . .
C00Q C 0.59240(17) 0.32256(14) 0.15889(13) 0.0255(3) Uani 1 1 d . . . . .
C00R C 0.77172(18) 0.61677(15) 0.45137(14) 0.0274(3) Uani 1 1 d . . . . .
C00S C 0.85489(18) 0.86065(14) 0.09314(14) 0.0256(3) Uani 1 1 d . . . . .
C00T C 0.1274(2) 0.88948(18) 0.58186(14) 0.0369(4) Uani 1 1 d . . . . .
C00U C 0.49180(19) 0.30111(16) 0.09094(16) 0.0348(4) Uani 1 1 d . . . . .
H00A H 0.426375 0.367608 0.081603 0.052 Uiso 1 1 calc R U . . .
H00B H 0.427186 0.223521 0.132661 0.052 Uiso 1 1 calc R U . . .
H00C H 0.557519 0.298485 0.015086 0.052 Uiso 1 1 calc R U . . .
C00V C 0.3740(2) 0.93147(16) 0.43128(15) 0.0350(4) Uani 1 1 d . . . . .
H00V H 0.466854 0.983086 0.387652 0.042 Uiso 1 1 calc R U . . .
C00W C 0.32984(19) 0.87590(15) 0.17710(14) 0.0304(4) Uani 1 1 d . . . . .
C00X C 0.6952(2) 0.21817(15) 0.17435(16) 0.0361(4) Uani 1 1 d . . . . .
H00D H 0.762119 0.215818 0.098743 0.054 Uiso 1 1 calc R U . . .
H00E H 0.630555 0.140503 0.215431 0.054 Uiso 1 1 calc R U . . .
H00F H 0.758240 0.231768 0.218728 0.054 Uiso 1 1 calc R U . . .
C00Y C 0.2159(2) 0.74795(16) 0.47418(15) 0.0368(4) Uani 1 1 d . . . . .
H00Y H 0.199596 0.673312 0.460179 0.044 Uiso 1 1 calc R U . . .
C00Z C 0.4861(2) 0.31948(16) 0.27835(15) 0.0396(4) Uani 1 1 d . . . . .
H00G H 0.547725 0.331934 0.324083 0.059 Uiso 1 1 calc R U . . .
H00H H 0.424362 0.240253 0.316434 0.059 Uiso 1 1 calc R U . . .
H00J H 0.417893 0.384296 0.271196 0.059 Uiso 1 1 calc R U . . .
C010 C 0.2630(2) 0.96313(17) 0.51686(16) 0.0408(4) Uani 1 1 d . . . . .
H010 H 0.280370 1.037267 0.531379 0.049 Uiso 1 1 calc R U . . .
C011 C 0.1063(2) 0.78137(19) 0.55981(16) 0.0419(5) Uani 1 1 d . . . . .
H011 H 0.014450 0.728784 0.604466 0.050 Uiso 1 1 calc R U . . .
C012 C 0.0059(3) 0.9275(2) 0.67263(17) 0.0578(6) Uani 1 1 d . . . . .
H01A H 0.052923 0.951778 0.722223 0.087 Uiso 1 1 calc R U . . .
H01B H -0.073202 0.859027 0.719059 0.087 Uiso 1 1 calc R U . . .
H01C H -0.040981 0.996399 0.635642 0.087 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F001 C00S 1.3385(18) . ?
F002 C00S 1.3276(18) . ?
F003 C00R 1.3347(18) . ?
F004 C00S 1.3442(17) . ?
F005 C00R 1.3325(19) . ?
F006 C00R 1.3274(18) . ?
F007 C00W 1.3251(19) . ?
F008 C00W 1.3353(19) . ?
O009 H009 0.8400 . ?
O009 C00G 1.3704(17) . ?
F00A C00W 1.335(2) . ?
O00B C00J 1.2085(18) . ?
N00C N00D 1.3332(18) . ?
N00C C00H 1.3003(19) . ?
N00D C00L 1.405(2) . ?
N00D C00P 1.4469(19) . ?
C00E C00K 1.389(2) . ?
C00E C00N 1.388(2) . ?
C00E C00O 1.5390(19) . ?
C00F C00G 1.406(2) . ?
C00F C00K 1.394(2) . ?
C00F C00Q 1.530(2) . ?
C00G C00I 1.381(2) . ?
C00H C00J 1.470(2) . ?
C00H C00O 1.529(2) . ?
C00I H00I 0.9500 . ?
C00I C00N 1.386(2) . ?
C00J C00R 1.550(2) . ?
C00K H00K 0.9500 . ?
C00L C00M 1.323(2) . ?
C00L C00W 1.506(2) . ?
C00M H00M 0.9500 . ?
C00M C00O 1.509(2) . ?
C00N H00N 0.9500 . ?
C00O C00S 1.537(2) . ?
C00P C00V 1.378(2) . ?
C00P C00Y 1.375(2) . ?
C00Q C00U 1.532(2) . ?
C00Q C00X 1.540(2) . ?
C00Q C00Z 1.527(2) . ?
C00T C010 1.380(3) . ?
C00T C011 1.383(3) . ?
C00T C012 1.506(2) . ?
C00U H00A 0.9800 . ?
C00U H00B 0.9800 . ?
C00U H00C 0.9800 . ?
C00V H00V 0.9500 . ?
C00V C010 1.380(2) . ?
C00X H00D 0.9800 . ?
C00X H00E 0.9800 . ?
C00X H00F 0.9800 . ?
C00Y H00Y 0.9500 . ?
C00Y C011 1.385(3) . ?
C00Z H00G 0.9800 . ?
C00Z H00H 0.9800 . ?
C00Z H00J 0.9800 . ?
C010 H010 0.9500 . ?
C011 H011 0.9500 . ?
C012 H01A 0.9800 . ?
C012 H01B 0.9800 . ?
C012 H01C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00G O009 H009 109.5 . . ?
C00H N00C N00D 121.02(13) . . ?
N00C N00D C00L 120.15(12) . . ?
N00C N00D C00P 115.05(12) . . ?
C00L N00D C00P 124.80(12) . . ?
C00K C00E C00O 117.46(12) . . ?
C00N C00E C00K 118.78(13) . . ?
C00N C00E C00O 123.51(13) . . ?
C00G C00F C00Q 122.05(13) . . ?
C00K C00F C00G 115.97(13) . . ?
C00K C00F C00Q 121.97(13) . . ?
O009 C00G C00F 118.45(13) . . ?
O009 C00G C00I 120.36(13) . . ?
C00I C00G C00F 121.19(13) . . ?
N00C C00H C00J 113.63(13) . . ?
N00C C00H C00O 125.70(13) . . ?
C00J C00H C00O 120.55(13) . . ?
C00G C00I H00I 119.4 . . ?
C00G C00I C00N 121.25(13) . . ?
C00N C00I H00I 119.4 . . ?
O00B C00J C00H 125.25(14) . . ?
O00B C00J C00R 117.18(13) . . ?
C00H C00J C00R 117.55(13) . . ?
C00E C00K C00F 123.56(13) . . ?
C00E C00K H00K 118.2 . . ?
C00F C00K H00K 118.2 . . ?
N00D C00L C00W 118.04(13) . . ?
C00M C00L N00D 121.49(14) . . ?
C00M C00L C00W 120.45(14) . . ?
C00L C00M H00M 118.4 . . ?
C00L C00M C00O 123.14(14) . . ?
C00O C00M H00M 118.4 . . ?
C00E C00N H00N 120.4 . . ?
C00I C00N C00E 119.22(14) . . ?
C00I C00N H00N 120.4 . . ?
C00H C00O C00E 113.37(12) . . ?
C00H C00O C00S 107.52(12) . . ?
C00M C00O C00E 107.96(11) . . ?
C00M C00O C00H 107.02(12) . . ?
C00M C00O C00S 106.76(12) . . ?
C00S C00O C00E 113.81(12) . . ?
C00V C00P N00D 118.81(14) . . ?
C00Y C00P N00D 120.65(14) . . ?
C00Y C00P C00V 120.55(15) . . ?
C00F C00Q C00U 109.21(13) . . ?
C00F C00Q C00X 110.21(13) . . ?
C00U C00Q C00X 109.81(13) . . ?
C00Z C00Q C00F 112.19(12) . . ?
C00Z C00Q C00U 107.79(14) . . ?
C00Z C00Q C00X 107.58(14) . . ?
F003 C00R C00J 111.78(13) . . ?
F005 C00R F003 108.38(13) . . ?
F005 C00R C00J 112.49(12) . . ?
F006 C00R F003 106.96(12) . . ?
F006 C00R F005 107.22(13) . . ?
F006 C00R C00J 109.76(13) . . ?
F001 C00S F004 106.43(12) . . ?
F001 C00S C00O 111.93(12) . . ?
F002 C00S F001 107.61(12) . . ?
F002 C00S F004 107.05(12) . . ?
F002 C00S C00O 113.56(12) . . ?
F004 C00S C00O 109.90(12) . . ?
C010 C00T C011 117.95(16) . . ?
C010 C00T C012 120.58(19) . . ?
C011 C00T C012 121.46(19) . . ?
C00Q C00U H00A 109.5 . . ?
C00Q C00U H00B 109.5 . . ?
C00Q C00U H00C 109.5 . . ?
H00A C00U H00B 109.5 . . ?
H00A C00U H00C 109.5 . . ?
H00B C00U H00C 109.5 . . ?
C00P C00V H00V 120.3 . . ?
C00P C00V C010 119.38(16) . . ?
C010 C00V H00V 120.3 . . ?
F007 C00W F008 107.08(13) . . ?
F007 C00W F00A 107.11(13) . . ?
F007 C00W C00L 111.08(13) . . ?
F008 C00W C00L 111.95(13) . . ?
F00A C00W F008 107.00(13) . . ?
F00A C00W C00L 112.32(14) . . ?
C00Q C00X H00D 109.5 . . ?
C00Q C00X H00E 109.5 . . ?
C00Q C00X H00F 109.5 . . ?
H00D C00X H00E 109.5 . . ?
H00D C00X H00F 109.5 . . ?
H00E C00X H00F 109.5 . . ?
C00P C00Y H00Y 120.4 . . ?
C00P C00Y C011 119.10(17) . . ?
C011 C00Y H00Y 120.4 . . ?
C00Q C00Z H00G 109.5 . . ?
C00Q C00Z H00H 109.5 . . ?
C00Q C00Z H00J 109.5 . . ?
H00G C00Z H00H 109.5 . . ?
H00G C00Z H00J 109.5 . . ?
H00H C00Z H00J 109.5 . . ?
C00T C010 H010 119.3 . . ?
C00V C010 C00T 121.46(17) . . ?
C00V C010 H010 119.3 . . ?
C00T C011 C00Y 121.54(17) . . ?
C00T C011 H011 119.2 . . ?
C00Y C011 H011 119.2 . . ?
C00T C012 H01A 109.5 . . ?
C00T C012 H01B 109.5 . . ?
C00T C012 H01C 109.5 . . ?
H01A C012 H01B 109.5 . . ?
H01A C012 H01C 109.5 . . ?
H01B C012 H01C 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
O009 C00G C00I C00N 179.09(13) . . . . ?
O00B C00J C00R F003 122.68(15) . . . . ?
O00B C00J C00R F005 -115.11(15) . . . . ?
O00B C00J C00R F006 4.2(2) . . . . ?
N00C N00D C00L C00M -7.4(2) . . . . ?
N00C N00D C00L C00W 170.82(13) . . . . ?
N00C N00D C00P C00V 87.81(18) . . . . ?
N00C N00D C00P C00Y -92.09(18) . . . . ?
N00C C00H C00J O00B 173.76(14) . . . . ?
N00C C00H C00J C00R -8.15(19) . . . . ?
N00C C00H C00O C00E -131.54(15) . . . . ?
N00C C00H C00O C00M -12.62(19) . . . . ?
N00C C00H C00O C00S 101.77(16) . . . . ?
N00D N00C C00H C00J -178.63(13) . . . . ?
N00D N00C C00H C00O 5.3(2) . . . . ?
N00D C00L C00M C00O -1.8(2) . . . . ?
N00D C00L C00W F007 -177.83(13) . . . . ?
N00D C00L C00W F008 62.52(19) . . . . ?
N00D C00L C00W F00A -57.88(19) . . . . ?
N00D C00P C00V C010 178.71(16) . . . . ?
N00D C00P C00Y C011 -178.87(16) . . . . ?
C00E C00O C00S F001 66.71(16) . . . . ?
C00E C00O C00S F002 -55.39(17) . . . . ?
C00E C00O C00S F004 -175.26(12) . . . . ?
C00F C00G C00I C00N -0.9(2) . . . . ?
C00G C00F C00K C00E -1.7(2) . . . . ?
C00G C00F C00Q C00U -62.56(18) . . . . ?
C00G C00F C00Q C00X 58.15(19) . . . . ?
C00G C00F C00Q C00Z 178.00(15) . . . . ?
C00G C00I C00N C00E -0.5(2) . . . . ?
C00H N00C N00D C00L 5.7(2) . . . . ?
C00H N00C N00D C00P -173.95(14) . . . . ?
C00H C00J C00R F003 -55.56(18) . . . . ?
C00H C00J C00R F005 66.64(17) . . . . ?
C00H C00J C00R F006 -174.07(13) . . . . ?
C00H C00O C00S F001 -166.86(12) . . . . ?
C00H C00O C00S F002 71.05(15) . . . . ?
C00H C00O C00S F004 -48.82(16) . . . . ?
C00J C00H C00O C00E 52.68(18) . . . . ?
C00J C00H C00O C00M 171.61(12) . . . . ?
C00J C00H C00O C00S -74.01(16) . . . . ?
C00K C00E C00N C00I 0.8(2) . . . . ?
C00K C00E C00O C00H 42.25(17) . . . . ?
C00K C00E C00O C00M -76.13(16) . . . . ?
C00K C00E C00O C00S 165.55(13) . . . . ?
C00K C00F C00G O009 -178.02(13) . . . . ?
C00K C00F C00G C00I 2.0(2) . . . . ?
C00K C00F C00Q C00U 116.83(15) . . . . ?
C00K C00F C00Q C00X -122.46(15) . . . . ?
C00K C00F C00Q C00Z -2.6(2) . . . . ?
C00L N00D C00P C00V -91.78(19) . . . . ?
C00L N00D C00P C00Y 88.3(2) . . . . ?
C00L C00M C00O C00E 132.83(15) . . . . ?
C00L C00M C00O C00H 10.46(19) . . . . ?
C00L C00M C00O C00S -104.43(17) . . . . ?
C00M C00L C00W F007 0.4(2) . . . . ?
C00M C00L C00W F008 -119.20(16) . . . . ?
C00M C00L C00W F00A 120.39(16) . . . . ?
C00M C00O C00S F001 -52.30(15) . . . . ?
C00M C00O C00S F002 -174.40(12) . . . . ?
C00M C00O C00S F004 65.73(15) . . . . ?
C00N C00E C00K C00F 0.4(2) . . . . ?
C00N C00E C00O C00H -143.61(14) . . . . ?
C00N C00E C00O C00M 98.01(16) . . . . ?
C00N C00E C00O C00S -20.3(2) . . . . ?
C00O C00E C00K C00F 174.83(13) . . . . ?
C00O C00E C00N C00I -173.28(13) . . . . ?
C00O C00H C00J O00B -10.0(2) . . . . ?
C00O C00H C00J C00R 168.11(13) . . . . ?
C00P N00D C00L C00M 172.13(15) . . . . ?
C00P N00D C00L C00W -9.6(2) . . . . ?
C00P C00V C010 C00T 0.3(3) . . . . ?
C00P C00Y C011 C00T 0.0(3) . . . . ?
C00Q C00F C00G O009 1.4(2) . . . . ?
C00Q C00F C00G C00I -178.60(14) . . . . ?
C00Q C00F C00K C00E 178.82(13) . . . . ?
C00V C00P C00Y C011 1.2(3) . . . . ?
C00W C00L C00M C00O 179.94(14) . . . . ?
C00Y C00P C00V C010 -1.4(3) . . . . ?
C010 C00T C011 C00Y -1.0(3) . . . . ?
C011 C00T C010 C00V 0.9(3) . . . . ?
C012 C00T C010 C00V -178.27(18) . . . . ?
C012 C00T C011 C00Y 178.10(18) . . . . ?

_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_ww21
_database_code_depnum_ccdc_archive 'CCDC 2013788'
loop_
_audit_author_name
_audit_author_address
HEXAFLUOROACETYLACETONE-CWYY-two
;Fuzhou University
China
;
_audit_update_record             
;
2020-07-03 deposited with the CCDC.	2020-10-02 downloaded from the CCDC.
;
_audit_creation_date             2020-07-01
_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         'C35 H33 F9 N2 O2'
_chemical_formula_sum            'C35 H33 F9 N2 O2'
_chemical_formula_weight         684.63
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.239(5)
_cell_length_b                   11.002(5)
_cell_length_c                   16.085(8)
_cell_angle_alpha                72.990(6)
_cell_angle_beta                 87.195(6)
_cell_angle_gamma                72.246(6)
_cell_volume                     1648.6(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2003
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.024
_cell_measurement_theta_min      2.432
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6573
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.0739 before and 0.0475 after correction.
The Ratio of minimum to maximum transmission is 0.8816.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             708
_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  0.0477
_diffrn_reflns_av_unetI/netI     0.0891
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11422
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.032
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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                3130
_reflns_number_total             5748
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     472
_refine_ls_number_reflns         5748
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.1268
_refine_ls_R_factor_gt           0.0668
_refine_ls_restrained_S_all      0.981
_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)+(0.1300P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2051
_refine_ls_wR_factor_ref         0.2280
_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. Uiso/Uaniso restraints and constraints
Uanis(C33) \\sim Ueq, Uanis(C38) \\sim Ueq, Uanis(C37) \\sim Ueq, Uanis(C36)
\\sim Ueq, Uanis(C35) \\sim Ueq, Uanis(C34) \\sim Ueq: with sigma of 0.02 and
sigma for terminal atoms of 0.04
3. Others
 Sof(C38)=Sof(H38A)=Sof(H38B)=Sof(H38C)=Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(H36C)=
 Sof(C34)=Sof(H34A)=Sof(H34B)=Sof(H34C)=1-FVAR(1)
 Sof(C37)=Sof(H37A)=Sof(H37B)=Sof(H37C)=Sof(C33)=Sof(H33A)=Sof(H33B)=Sof(H33C)=
 Sof(C35)=Sof(H35A)=Sof(H35B)=Sof(H35C)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C15(H15), C27(H27), C10(H10), C17(H17), C29(H29), C4(H4), C30(H30),
 C6(H6), C7(H7), C3(H3)
4.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C1(H1A,H1B,
 H1C), C37(H37A,H37B,H37C), C33(H33A,H33B,H33C), C35(H35A,H35B,H35C), C38(H38A,
 H38B,H38C), C36(H36A,H36B,H36C), C34(H34A,H34B,H34C)
4.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3173(2) 0.6751(2) 0.13535(16) 0.0356(7) Uani 1 1 d . . . . .
F8 F 0.0797(2) 0.9970(2) 0.07322(15) 0.0527(7) Uani 1 1 d . . . . .
F9 F 0.2569(3) 0.9062(2) 0.01319(17) 0.0610(8) Uani 1 1 d . . . . .
F6 F 0.4087(3) 0.6554(3) 0.31007(19) 0.0700(8) Uani 1 1 d . . . . .
F7 F 0.2764(3) 0.9328(2) 0.13797(17) 0.0622(8) Uani 1 1 d . . . . .
C12 C 0.1369(4) 0.7549(3) 0.2244(2) 0.0313(9) Uani 1 1 d . . . . .
F4 F 0.2512(3) 0.7369(3) 0.38694(18) 0.0716(8) Uani 1 1 d . . . . .
O2 O 0.2494(3) 0.6846(3) -0.03156(19) 0.0509(8) Uani 1 1 d . . . . .
H2 H 0.295310 0.710907 -0.004432 0.076 Uiso 1 1 calc GR . . . .
N2 N 0.0455(3) 0.8555(3) 0.2379(2) 0.0356(8) Uani 1 1 d . . . . .
F5 F 0.3435(3) 0.5265(3) 0.41926(17) 0.0737(9) Uani 1 1 d . . . . .
N1 N -0.0178(3) 0.8407(3) 0.3145(2) 0.0400(8) Uani 1 1 d . . . . .
C14 C 0.2628(4) 0.5115(3) 0.2559(3) 0.0344(9) Uani 1 1 d . . . . .
F3 F -0.2610(3) 0.7880(3) 0.3770(2) 0.0886(10) Uani 1 1 d . . . . .
C24 C 0.1802(3) 0.7649(3) 0.1330(2) 0.0328(9) Uani 1 1 d . . . . .
C31 C 0.1213(4) 0.6988(4) 0.0024(3) 0.0392(10) Uani 1 1 d . . . . .
C19 C 0.3265(4) 0.5430(3) 0.1785(3) 0.0342(9) Uani 1 1 d . . . . .
C11 C 0.1924(4) 0.6233(3) 0.2956(2) 0.0364(9) Uani 1 1 d . . . . .
C28 C -0.1441(4) 0.7155(4) 0.0590(3) 0.0381(10) Uani 1 1 d . . . . .
C26 C 0.0842(4) 0.7333(3) 0.0791(2) 0.0314(9) Uani 1 1 d . . . . .
C18 C 0.4036(4) 0.4454(4) 0.1447(3) 0.0394(10) Uani 1 1 d . . . . .
H18 H 0.449131 0.467283 0.093650 0.047 Uiso 1 1 calc R . . . .
C5 C -0.0981(4) 0.9638(4) 0.3290(3) 0.0395(10) Uani 1 1 d . . . . .
F1 F -0.1603(3) 0.5789(3) 0.4213(2) 0.0882(10) Uani 1 1 d . . . . .
C15 C 0.2736(4) 0.3792(4) 0.2962(3) 0.0404(10) Uani 1 1 d . . . . .
H15 H 0.230148 0.357404 0.348094 0.048 Uiso 1 1 calc R . . . .
C27 C -0.0497(3) 0.7402(3) 0.1042(2) 0.0349(9) Uani 1 1 d . . . . .
H27 H -0.076675 0.763016 0.155095 0.042 Uiso 1 1 calc R . . . .
C10 C 0.0706(4) 0.6060(4) 0.3465(3) 0.0432(10) Uani 1 1 d . . . . .
H10 H 0.060611 0.521547 0.369576 0.052 Uiso 1 1 calc R . . . .
C17 C 0.4139(4) 0.3140(4) 0.1866(3) 0.0441(10) Uani 1 1 d . . . . .
H17 H 0.467445 0.248088 0.163185 0.053 Uiso 1 1 calc R . . . .
C9 C -0.0244(4) 0.7132(4) 0.3589(3) 0.0395(10) Uani 1 1 d . . . . .
C20 C 0.3495(4) 0.1340(4) 0.3071(3) 0.0479(11) Uani 1 1 d . . . . .
C16 C 0.3476(4) 0.2770(4) 0.2617(3) 0.0392(10) Uani 1 1 d . . . . .
C25 C 0.1983(4) 0.9008(4) 0.0895(3) 0.0412(10) Uani 1 1 d . . . . .
C32 C -0.2859(4) 0.7188(4) 0.0942(3) 0.0455(11) Uani 1 1 d . . . . .
C29 C -0.1019(4) 0.6830(4) -0.0165(3) 0.0481(11) Uani 1 1 d . . . . .
H29 H -0.162991 0.666052 -0.049292 0.058 Uiso 1 1 calc R . . . .
F2 F -0.1321(3) 0.7038(3) 0.4921(2) 0.0914(11) Uani 1 1 d . . . . .
C4 C -0.1046(4) 0.9780(4) 0.4108(3) 0.0501(11) Uani 1 1 d . . . . .
H4 H -0.057170 0.907296 0.457270 0.060 Uiso 1 1 calc R . . . .
C30 C 0.0286(4) 0.6751(4) -0.0444(3) 0.0461(11) Uani 1 1 d . . . . .
H30 H 0.054212 0.653348 -0.095756 0.055 Uiso 1 1 calc R . . . .
C6 C -0.1616(4) 1.0709(4) 0.2597(3) 0.0464(11) Uani 1 1 d . . . . .
H6 H -0.154420 1.063335 0.203430 0.056 Uiso 1 1 calc R . . . .
C13 C 0.3000(4) 0.6353(4) 0.3529(3) 0.0489(11) Uani 1 1 d . . . . .
C7 C -0.2358(4) 1.1892(4) 0.2744(3) 0.0553(12) Uani 1 1 d . . . . .
H7 H -0.279388 1.261235 0.227403 0.066 Uiso 1 1 calc R . . . .
C2 C -0.2473(4) 1.2042(4) 0.3566(3) 0.0525(12) Uani 1 1 d . . . . .
C23 C 0.4419(6) 0.0375(4) 0.2616(4) 0.0718(15) Uani 1 1 d . . . . .
H23A H 0.409710 0.062557 0.202115 0.108 Uiso 1 1 calc GR . . . .
H23B H 0.439722 -0.051476 0.290617 0.108 Uiso 1 1 calc GR . . . .
H23C H 0.534265 0.040823 0.263494 0.108 Uiso 1 1 calc GR . . . .
C3 C -0.1816(5) 1.0973(5) 0.4247(3) 0.0560(12) Uani 1 1 d . . . . .
H3 H -0.188800 1.104772 0.480964 0.067 Uiso 1 1 calc R . . . .
C21 C 0.4070(6) 0.0916(5) 0.4000(3) 0.0791(17) Uani 1 1 d . . . . .
H21A H 0.495992 0.103736 0.399709 0.119 Uiso 1 1 calc GR . . . .
H21B H 0.414770 -0.000754 0.426819 0.119 Uiso 1 1 calc GR . . . .
H21C H 0.346606 0.144912 0.432296 0.119 Uiso 1 1 calc GR . . . .
C22 C 0.2057(5) 0.1241(5) 0.3066(4) 0.0897(19) Uani 1 1 d . . . . .
H22A H 0.147756 0.181382 0.337406 0.135 Uiso 1 1 calc GR . . . .
H22B H 0.207238 0.033578 0.334336 0.135 Uiso 1 1 calc GR . . . .
H22C H 0.170551 0.150943 0.247559 0.135 Uiso 1 1 calc GR . . . .
C1 C -0.3331(6) 1.3343(5) 0.3721(4) 0.0909(19) Uani 1 1 d . . . . .
H1A H -0.274124 1.384247 0.378654 0.136 Uiso 1 1 calc GR . . . .
H1B H -0.383013 1.315537 0.423947 0.136 Uiso 1 1 calc GR . . . .
H1C H -0.396604 1.385383 0.323345 0.136 Uiso 1 1 calc GR . . . .
C8 C -0.1450(5) 0.6975(5) 0.4110(4) 0.0616(13) Uani 1 1 d . . . . .
C37 C -0.3530(17) 0.8403(15) 0.1218(14) 0.089(6) Uani 0.62(3) 1 d . U P A 1
H37A H -0.295244 0.845508 0.165047 0.133 Uiso 0.62(3) 1 calc GR . P A 1
H37B H -0.439763 0.835872 0.145725 0.133 Uiso 0.62(3) 1 calc GR . P A 1
H37C H -0.367386 0.918014 0.072351 0.133 Uiso 0.62(3) 1 calc GR . P A 1
C33 C -0.2704(18) 0.5951(18) 0.1733(12) 0.100(6) Uani 0.62(3) 1 d . U P A 1
H33A H -0.209691 0.517919 0.160210 0.150 Uiso 0.62(3) 1 calc GR . P A 1
H33B H -0.358689 0.582345 0.186276 0.150 Uiso 0.62(3) 1 calc GR . P A 1
H33C H -0.233348 0.607921 0.222603 0.150 Uiso 0.62(3) 1 calc GR . P A 1
C35 C -0.3831(12) 0.715(3) 0.0271(9) 0.097(6) Uani 0.62(3) 1 d . U P A 1
H35A H -0.383830 0.783463 -0.026134 0.145 Uiso 0.62(3) 1 calc GR . P A 1
H35B H -0.474042 0.729731 0.048642 0.145 Uiso 0.62(3) 1 calc GR . P A 1
H35C H -0.352897 0.629412 0.016607 0.145 Uiso 0.62(3) 1 calc GR . P A 1
C38 C -0.319(3) 0.791(4) 0.164(2) 0.102(11) Uani 0.38(3) 1 d . U P A 2
H38A H -0.255866 0.742484 0.213442 0.153 Uiso 0.38(3) 1 calc GR . P A 2
H38B H -0.410909 0.797481 0.181873 0.153 Uiso 0.38(3) 1 calc GR . P A 2
H38C H -0.310216 0.879260 0.141043 0.153 Uiso 0.38(3) 1 calc GR . P A 2
C36 C -0.3899(16) 0.812(3) 0.0184(14) 0.090(8) Uani 0.38(3) 1 d . U P A 2
H36A H -0.369931 0.895032 -0.003854 0.135 Uiso 0.38(3) 1 calc GR . P A 2
H36B H -0.481272 0.828163 0.039264 0.135 Uiso 0.38(3) 1 calc GR . P A 2
H36C H -0.383000 0.770275 -0.027054 0.135 Uiso 0.38(3) 1 calc GR . P A 2
C34 C -0.297(3) 0.587(2) 0.121(2) 0.089(10) Uani 0.38(3) 1 d . U P A 2
H34A H -0.241101 0.535494 0.086467 0.134 Uiso 0.38(3) 1 calc GR . P A 2
H34B H -0.391250 0.591020 0.114323 0.134 Uiso 0.38(3) 1 calc GR . P A 2
H34C H -0.267259 0.545716 0.181390 0.134 Uiso 0.38(3) 1 calc GR . 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 C24 1.444(4) . ?
O1 C19 1.391(4) . ?
F8 C25 1.323(4) . ?
F9 C25 1.333(5) . ?
F6 C13 1.322(5) . ?
F7 C25 1.328(5) . ?
C12 N2 1.281(4) . ?
C12 C24 1.497(5) . ?
C12 C11 1.524(5) . ?
F4 C13 1.337(5) . ?
O2 C31 1.378(4) . ?
N2 N1 1.353(4) . ?
F5 C13 1.321(5) . ?
N1 C5 1.433(5) . ?
N1 C9 1.396(5) . ?
C14 C19 1.379(5) . ?
C14 C11 1.520(5) . ?
C14 C15 1.381(5) . ?
F3 C8 1.314(5) . ?
C24 C26 1.519(5) . ?
C24 C25 1.517(5) . ?
C31 C26 1.397(5) . ?
C31 C30 1.367(5) . ?
C19 C18 1.363(5) . ?
C11 C10 1.488(5) . ?
C11 C13 1.530(6) . ?
C28 C27 1.371(5) . ?
C28 C32 1.526(5) . ?
C28 C29 1.379(6) . ?
C26 C27 1.397(5) . ?
C18 C17 1.378(5) . ?
C5 C4 1.365(6) . ?
C5 C6 1.374(5) . ?
F1 C8 1.323(5) . ?
C15 C16 1.396(5) . ?
C10 C9 1.340(5) . ?
C17 C16 1.374(6) . ?
C9 C8 1.484(6) . ?
C20 C16 1.523(5) . ?
C20 C23 1.527(6) . ?
C20 C21 1.519(6) . ?
C20 C22 1.511(7) . ?
C32 C37 1.488(17) . ?
C32 C33 1.539(14) . ?
C32 C35 1.521(10) . ?
C32 C38 1.53(3) . ?
C32 C36 1.550(18) . ?
C32 C34 1.43(2) . ?
C29 C30 1.373(6) . ?
F2 C8 1.341(6) . ?
C4 C3 1.385(6) . ?
C6 C7 1.374(5) . ?
C7 C2 1.375(6) . ?
C2 C3 1.368(6) . ?
C2 C1 1.517(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
C19 O1 C24 112.7(3) . . ?
N2 C12 C24 117.7(3) . . ?
N2 C12 C11 122.5(4) . . ?
C24 C12 C11 119.6(3) . . ?
C12 N2 N1 119.3(3) . . ?
N2 N1 C5 114.1(3) . . ?
N2 N1 C9 117.3(3) . . ?
C9 N1 C5 126.7(3) . . ?
C19 C14 C11 118.1(3) . . ?
C19 C14 C15 118.4(3) . . ?
C15 C14 C11 123.3(4) . . ?
O1 C24 C12 108.8(3) . . ?
O1 C24 C26 109.6(3) . . ?
O1 C24 C25 102.8(3) . . ?
C12 C24 C26 113.2(3) . . ?
C12 C24 C25 110.3(3) . . ?
C25 C24 C26 111.5(3) . . ?
O2 C31 C26 124.4(3) . . ?
C30 C31 O2 115.1(4) . . ?
C30 C31 C26 120.5(4) . . ?
C14 C19 O1 120.4(3) . . ?
C18 C19 O1 118.8(3) . . ?
C18 C19 C14 120.7(3) . . ?
C12 C11 C13 109.2(3) . . ?
C14 C11 C12 110.4(3) . . ?
C14 C11 C13 107.5(3) . . ?
C10 C11 C12 104.4(3) . . ?
C10 C11 C14 114.9(3) . . ?
C10 C11 C13 110.3(3) . . ?
C27 C28 C32 120.6(4) . . ?
C27 C28 C29 116.6(4) . . ?
C29 C28 C32 122.8(3) . . ?
C31 C26 C24 123.4(3) . . ?
C27 C26 C24 120.3(3) . . ?
C27 C26 C31 116.2(3) . . ?
C19 C18 C17 119.6(4) . . ?
C4 C5 N1 120.2(4) . . ?
C4 C5 C6 119.7(4) . . ?
C6 C5 N1 119.9(4) . . ?
C14 C15 C16 122.4(4) . . ?
C28 C27 C26 124.5(4) . . ?
C9 C10 C11 119.5(3) . . ?
C16 C17 C18 122.2(4) . . ?
N1 C9 C8 119.8(3) . . ?
C10 C9 N1 119.6(4) . . ?
C10 C9 C8 120.2(4) . . ?
C16 C20 C23 111.1(4) . . ?
C21 C20 C16 109.9(3) . . ?
C21 C20 C23 107.1(4) . . ?
C22 C20 C16 109.5(4) . . ?
C22 C20 C23 108.9(4) . . ?
C22 C20 C21 110.3(4) . . ?
C15 C16 C20 119.6(4) . . ?
C17 C16 C15 116.5(4) . . ?
C17 C16 C20 123.9(4) . . ?
F8 C25 F9 106.2(3) . . ?
F8 C25 F7 107.1(3) . . ?
F8 C25 C24 112.1(3) . . ?
F9 C25 C24 111.9(3) . . ?
F7 C25 F9 106.9(3) . . ?
F7 C25 C24 112.2(3) . . ?
C28 C32 C33 108.6(7) . . ?
C28 C32 C38 111.4(10) . . ?
C28 C32 C36 105.7(8) . . ?
C37 C32 C28 112.6(8) . . ?
C37 C32 C33 108.7(10) . . ?
C37 C32 C35 106.9(9) . . ?
C35 C32 C28 112.0(5) . . ?
C35 C32 C33 107.8(8) . . ?
C38 C32 C36 103.3(12) . . ?
C34 C32 C28 109.8(10) . . ?
C34 C32 C38 114.2(15) . . ?
C34 C32 C36 111.9(12) . . ?
C30 C29 C28 121.4(4) . . ?
C5 C4 C3 120.2(4) . . ?
C31 C30 C29 120.9(4) . . ?
C7 C6 C5 119.3(4) . . ?
F6 C13 F4 105.9(4) . . ?
F6 C13 C11 112.8(4) . . ?
F4 C13 C11 112.6(3) . . ?
F5 C13 F6 107.5(4) . . ?
F5 C13 F4 106.4(4) . . ?
F5 C13 C11 111.1(4) . . ?
C6 C7 C2 121.8(4) . . ?
C7 C2 C1 121.2(4) . . ?
C3 C2 C7 118.1(4) . . ?
C3 C2 C1 120.7(5) . . ?
C2 C3 C4 120.7(5) . . ?
F3 C8 F1 107.7(4) . . ?
F3 C8 C9 113.6(4) . . ?
F3 C8 F2 106.4(4) . . ?
F1 C8 C9 111.3(4) . . ?
F1 C8 F2 104.9(4) . . ?
F2 C8 C9 112.6(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
