# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1570123'
_audit_update_record             
;
2017-08-22 deposited with the CCDC.
2018-01-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H17 F6 N O2'
_chemical_formula_sum            'C21 H17 F6 N O2'
_chemical_formula_weight         429.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0070 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0130 0.0070 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0210 0.0120 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0330 0.0200 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.0952(18)
_cell_length_b                   10.010(2)
_cell_length_c                   10.595(2)
_cell_angle_alpha                95.63(3)
_cell_angle_beta                 93.85(3)
_cell_angle_gamma                103.51(3)
_cell_volume                     929.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    600
_cell_measurement_theta_min      3.8
_cell_measurement_theta_max      38.0

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.307
_shelx_estimated_absorpt_T_min   0.936
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_process_details   'Scala (Evans, 2005)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.96990
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  'MAR CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14805
_diffrn_reflns_av_unetI/netI     0.1171
_diffrn_reflns_av_R_equivalents  0.0823
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.722
_diffrn_reflns_theta_max         38.365
_diffrn_reflns_theta_full        35.587
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             3812
_reflns_number_gt                2997
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       Automar
_computing_cell_refinement       iMosflm
_computing_data_reduction        iMosflm
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0143P)²+0.3P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.023(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3812
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1458
_refine_ls_wR_factor_gt          0.1351
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.19144(12) 0.20933(11) 0.16647(11) 0.0282(3) Uani 1 1 d . . . . .
F2 F 0.33791(12) 0.35998(12) 0.07037(10) 0.0289(3) Uani 1 1 d . . . . .
F3 F 0.22111(13) 0.42609(12) 0.22650(12) 0.0306(3) Uani 1 1 d . . . . .
F4 F 0.60752(13) 0.27931(12) 0.02995(10) 0.0300(3) Uani 1 1 d . . . . .
F5 F 0.43450(13) 0.11100(12) 0.07838(11) 0.0297(3) Uani 1 1 d . . . . .
F6 F 0.67157(13) 0.11838(12) 0.12448(11) 0.0315(3) Uani 1 1 d . . . . .
O1 O 0.65293(13) 0.47822(12) 0.39420(12) 0.0165(3) Uani 1 1 d . . . . .
O2 O 0.51463(13) 0.25125(12) 0.46626(11) 0.0164(3) Uani 1 1 d . . . . .
C1 C 0.72819(19) 0.15960(18) 0.40524(18) 0.0181(4) Uani 1 1 d . . . . .
H1A H 0.7230 0.1115 0.4827 0.022 Uiso 1 1 calc R U . . .
H1B H 0.7606 0.1008 0.3372 0.022 Uiso 1 1 calc R U . . .
N2 N 0.84185(16) 0.29286(15) 0.43189(14) 0.0171(4) Uani 1 1 d . . . . .
C3 C 0.8556(2) 0.37365(18) 0.32334(17) 0.0177(4) Uani 1 1 d . . . . .
H3A H 0.8851 0.3198 0.2499 0.021 Uiso 1 1 calc R U . . .
H3B H 0.9362 0.4599 0.3459 0.021 Uiso 1 1 calc R U . . .
C3A C 0.7066(2) 0.40897(18) 0.28674(17) 0.0170(4) Uani 1 1 d . . . . .
C4 C 0.6955(2) 0.50886(19) 0.18813(18) 0.0213(4) Uani 1 1 d . . . . .
H4 H 0.7607 0.5309 0.1229 0.026 Uiso 1 1 calc R U . . .
C5 C 0.5760(2) 0.55839(19) 0.21260(19) 0.0222(4) Uani 1 1 d . . . . .
H5 H 0.5368 0.6217 0.1673 0.027 Uiso 1 1 calc R U . . .
C6 C 0.5141(2) 0.49259(18) 0.32897(18) 0.0174(4) Uani 1 1 d . . . . .
H6 H 0.4550 0.5467 0.3807 0.021 Uiso 1 1 calc R U . . .
C6A C 0.4286(2) 0.33534(18) 0.28428(17) 0.0167(4) Uani 1 1 d . . . . .
C7 C 0.3724(2) 0.25109(18) 0.39939(17) 0.0174(4) Uani 1 1 d . . . . .
H7 H 0.3018 0.2904 0.4520 0.021 Uiso 1 1 calc R U . . .
C8 C 0.3147(2) 0.09702(18) 0.35022(18) 0.0210(4) Uani 1 1 d . . . . .
H8 H 0.2121 0.0451 0.3368 0.025 Uiso 1 1 calc R U . . .
C9 C 0.4384(2) 0.05128(19) 0.33034(18) 0.0208(4) Uani 1 1 d . . . . .
H9 H 0.4426 -0.0404 0.3012 0.025 Uiso 1 1 calc R U . . .
C9A C 0.5723(2) 0.17751(17) 0.36437(17) 0.0167(4) Uani 1 1 d . . . . .
C9B C 0.5688(2) 0.27514(18) 0.25359(17) 0.0159(4) Uani 1 1 d . . . . .
C10 C 0.9880(2) 0.27150(19) 0.48143(18) 0.0191(4) Uani 1 1 d . . . . .
H10A H 1.0678 0.3576 0.4807 0.023 Uiso 1 1 calc R U . . .
H10B H 1.0145 0.1977 0.4248 0.023 Uiso 1 1 calc R U . . .
C11 C 0.9852(2) 0.23135(18) 0.61640(18) 0.0185(4) Uani 1 1 d . . . . .
C12 C 1.0818(2) 0.15262(19) 0.66006(19) 0.0220(4) Uani 1 1 d . . . . .
H12 H 1.1460 0.1199 0.6037 0.026 Uiso 1 1 calc R U . . .
C13 C 1.0854(2) 0.1213(2) 0.7860(2) 0.0265(5) Uani 1 1 d . . . . .
H13 H 1.1530 0.0691 0.8150 0.032 Uiso 1 1 calc R U . . .
C14 C 0.9898(2) 0.1667(2) 0.86851(19) 0.0275(5) Uani 1 1 d . . . . .
H14 H 0.9912 0.1449 0.9538 0.033 Uiso 1 1 calc R U . . .
C15 C 0.8921(2) 0.2442(2) 0.8254(2) 0.0266(5) Uani 1 1 d . . . . .
H15 H 0.8266 0.2753 0.8815 0.032 Uiso 1 1 calc R U . . .
C16 C 0.8899(2) 0.27639(19) 0.70079(19) 0.0220(4) Uani 1 1 d . . . . .
H16 H 0.8229 0.3296 0.6725 0.026 Uiso 1 1 calc R U . . .
C17 C 0.2969(2) 0.33048(19) 0.18580(18) 0.0201(4) Uani 1 1 d . . . . .
C18 C 0.5700(2) 0.19733(19) 0.12221(18) 0.0219(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C17 1.347(2) . ?
F2 C17 1.343(2) . ?
F3 C17 1.358(2) . ?
F4 C18 1.348(2) . ?
F5 C18 1.352(2) . ?
F6 C18 1.349(2) . ?
O1 C6 1.442(2) . ?
O1 C3A 1.447(2) . ?
O2 C7 1.432(2) . ?
O2 C9A 1.444(2) . ?
C1 N2 1.473(2) . ?
C1 C9A 1.510(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
N2 C3 1.465(2) . ?
N2 C10 1.466(2) . ?
C3 C3A 1.514(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3A C4 1.529(2) . ?
C3A C9B 1.598(2) . ?
C4 C5 1.326(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.533(2) . ?
C5 H5 0.9500 . ?
C6 C6A 1.594(3) . ?
C6 H6 1.0000 . ?
C6A C17 1.524(3) . ?
C6A C9B 1.572(3) . ?
C6A C7 1.595(2) . ?
C7 C8 1.534(3) . ?
C7 H7 1.0000 . ?
C8 C9 1.331(3) . ?
C8 H8 0.9500 . ?
C9 C9A 1.531(2) . ?
C9 H9 0.9500 . ?
C9A C9B 1.603(2) . ?
C9B C18 1.529(3) . ?
C10 C11 1.523(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.396(3) . ?
C11 C16 1.401(3) . ?
C12 C13 1.400(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.392(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.389(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?

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
C6 O1 C3A 97.01(14) . . ?
C7 O2 C9A 97.11(14) . . ?
N2 C1 C9A 112.22(14) . . ?
N2 C1 H1A 109.2 . . ?
C9A C1 H1A 109.2 . . ?
N2 C1 H1B 109.2 . . ?
C9A C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
C3 N2 C10 112.51(13) . . ?
C3 N2 C1 113.33(14) . . ?
C10 N2 C1 110.32(13) . . ?
N2 C3 C3A 110.50(13) . . ?
N2 C3 H3A 109.6 . . ?
C3A C3 H3A 109.6 . . ?
N2 C3 H3B 109.6 . . ?
C3A C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
O1 C3A C3 111.50(15) . . ?
O1 C3A C4 99.99(14) . . ?
C3 C3A C4 121.11(14) . . ?
O1 C3A C9B 100.19(12) . . ?
C3 C3A C9B 112.79(14) . . ?
C4 C3A C9B 108.57(15) . . ?
C5 C4 C3A 105.76(15) . . ?
C5 C4 H4 127.1 . . ?
C3A C4 H4 127.1 . . ?
C4 C5 C6 105.97(16) . . ?
C4 C5 H5 127.0 . . ?
C6 C5 H5 127.0 . . ?
O1 C6 C5 100.30(14) . . ?
O1 C6 C6A 101.77(13) . . ?
C5 C6 C6A 108.39(15) . . ?
O1 C6 H6 114.9 . . ?
C5 C6 H6 114.9 . . ?
C6A C6 H6 114.9 . . ?
C17 C6A C9B 123.26(16) . . ?
C17 C6A C6 109.17(14) . . ?
C9B C6A C6 99.53(13) . . ?
C17 C6A C7 111.20(14) . . ?
C9B C6A C7 99.91(13) . . ?
C6 C6A C7 113.25(14) . . ?
O2 C7 C8 100.66(14) . . ?
O2 C7 C6A 100.93(12) . . ?
C8 C7 C6A 109.39(14) . . ?
O2 C7 H7 114.7 . . ?
C8 C7 H7 114.7 . . ?
C6A C7 H7 114.7 . . ?
C9 C8 C7 105.68(15) . . ?
C9 C8 H8 127.2 . . ?
C7 C8 H8 127.2 . . ?
C8 C9 C9A 105.56(16) . . ?
C8 C9 H9 127.2 . . ?
C9A C9 H9 127.2 . . ?
O2 C9A C1 110.82(15) . . ?
O2 C9A C9 100.20(13) . . ?
C1 C9A C9 120.47(15) . . ?
O2 C9A C9B 101.49(13) . . ?
C1 C9A C9B 114.50(13) . . ?
C9 C9A C9B 106.86(15) . . ?
C18 C9B C6A 119.43(16) . . ?
C18 C9B C3A 113.34(14) . . ?
C6A C9B C3A 101.83(14) . . ?
C18 C9B C9A 111.69(14) . . ?
C6A C9B C9A 101.04(12) . . ?
C3A C9B C9A 108.22(15) . . ?
N2 C10 C11 112.39(14) . . ?
N2 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
N2 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
C12 C11 C16 118.51(17) . . ?
C12 C11 C10 120.50(16) . . ?
C16 C11 C10 120.95(16) . . ?
C11 C12 C13 120.79(18) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 119.99(19) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 119.58(18) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 120.35(18) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C11 120.78(18) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
F2 C17 F1 106.28(16) . . ?
F2 C17 F3 106.02(14) . . ?
F1 C17 F3 105.22(14) . . ?
F2 C17 C6A 114.66(15) . . ?
F1 C17 C6A 114.85(15) . . ?
F3 C17 C6A 109.06(16) . . ?
F4 C18 F6 105.57(14) . . ?
F4 C18 F5 105.49(15) . . ?
F6 C18 F5 106.27(15) . . ?
F4 C18 C9B 114.51(15) . . ?
F6 C18 C9B 111.08(16) . . ?
F5 C18 C9B 113.26(15) . . ?

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
C9A C1 N2 C3 -57.59(19) . . . . ?
C9A C1 N2 C10 175.22(14) . . . . ?
C10 N2 C3 C3A -172.55(15) . . . . ?
C1 N2 C3 C3A 61.41(19) . . . . ?
C6 O1 C3A C3 -178.71(13) . . . . ?
C6 O1 C3A C4 52.00(14) . . . . ?
C6 O1 C3A C9B -59.12(14) . . . . ?
N2 C3 C3A O1 54.63(18) . . . . ?
N2 C3 C3A C4 171.73(15) . . . . ?
N2 C3 C3A C9B -57.19(19) . . . . ?
O1 C3A C4 C5 -33.81(18) . . . . ?
C3 C3A C4 C5 -156.55(17) . . . . ?
C9B C3A C4 C5 70.59(19) . . . . ?
C3A C4 C5 C6 1.4(2) . . . . ?
C3A O1 C6 C5 -51.12(15) . . . . ?
C3A O1 C6 C6A 60.31(14) . . . . ?
C4 C5 C6 O1 31.49(19) . . . . ?
C4 C5 C6 C6A -74.70(19) . . . . ?
O1 C6 C6A C17 -166.19(13) . . . . ?
C5 C6 C6A C17 -61.02(18) . . . . ?
O1 C6 C6A C9B -35.86(15) . . . . ?
C5 C6 C6A C9B 69.31(17) . . . . ?
O1 C6 C6A C7 69.33(17) . . . . ?
C5 C6 C6A C7 174.50(14) . . . . ?
C9A O2 C7 C8 51.19(14) . . . . ?
C9A O2 C7 C6A -61.18(14) . . . . ?
C17 C6A C7 O2 171.07(14) . . . . ?
C9B C6A C7 O2 39.39(16) . . . . ?
C6 C6A C7 O2 -65.56(17) . . . . ?
C17 C6A C7 C8 65.54(19) . . . . ?
C9B C6A C7 C8 -66.13(17) . . . . ?
C6 C6A C7 C8 -171.09(14) . . . . ?
O2 C7 C8 C9 -31.70(17) . . . . ?
C6A C7 C8 C9 74.00(18) . . . . ?
C7 C8 C9 C9A -1.19(19) . . . . ?
C7 O2 C9A C1 179.85(12) . . . . ?
C7 O2 C9A C9 -51.86(15) . . . . ?
C7 O2 C9A C9B 57.85(14) . . . . ?
N2 C1 C9A O2 -64.55(18) . . . . ?
N2 C1 C9A C9 179.13(15) . . . . ?
N2 C1 C9A C9B 49.5(2) . . . . ?
C8 C9 C9A O2 33.39(18) . . . . ?
C8 C9 C9A C1 155.05(16) . . . . ?
C8 C9 C9A C9B -72.03(18) . . . . ?
C17 C6A C9B C18 -5.0(2) . . . . ?
C6 C6A C9B C18 -125.58(16) . . . . ?
C7 C6A C9B C18 118.60(16) . . . . ?
C17 C6A C9B C3A 120.64(17) . . . . ?
C6 C6A C9B C3A 0.08(15) . . . . ?
C7 C6A C9B C3A -115.74(14) . . . . ?
C17 C6A C9B C9A -127.87(16) . . . . ?
C6 C6A C9B C9A 111.57(14) . . . . ?
C7 C6A C9B C9A -4.25(16) . . . . ?
O1 C3A C9B C18 164.94(14) . . . . ?
C3 C3A C9B C18 -76.42(19) . . . . ?
C4 C3A C9B C18 60.67(19) . . . . ?
O1 C3A C9B C6A 35.36(16) . . . . ?
C3 C3A C9B C6A 154.00(14) . . . . ?
C4 C3A C9B C6A -68.91(16) . . . . ?
O1 C3A C9B C9A -70.59(16) . . . . ?
C3 C3A C9B C9A 48.05(18) . . . . ?
C4 C3A C9B C9A -174.86(14) . . . . ?
O2 C9A C9B C18 -159.57(14) . . . . ?
C1 C9A C9B C18 81.02(19) . . . . ?
C9 C9A C9B C18 -55.06(18) . . . . ?
O2 C9A C9B C6A -31.51(16) . . . . ?
C1 C9A C9B C6A -150.93(15) . . . . ?
C9 C9A C9B C6A 72.99(16) . . . . ?
O2 C9A C9B C3A 74.99(15) . . . . ?
C1 C9A C9B C3A -44.42(19) . . . . ?
C9 C9A C9B C3A 179.49(13) . . . . ?
C3 N2 C10 C11 161.11(15) . . . . ?
C1 N2 C10 C11 -71.25(19) . . . . ?
N2 C10 C11 C12 152.86(16) . . . . ?
N2 C10 C11 C16 -29.4(2) . . . . ?
C16 C11 C12 C13 -1.1(3) . . . . ?
C10 C11 C12 C13 176.72(16) . . . . ?
C11 C12 C13 C14 1.2(3) . . . . ?
C12 C13 C14 C15 -0.6(3) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
C14 C15 C16 C11 0.1(3) . . . . ?
C12 C11 C16 C15 0.4(3) . . . . ?
C10 C11 C16 C15 -177.37(17) . . . . ?
C9B C6A C17 F2 -41.9(2) . . . . ?
C6 C6A C17 F2 74.02(19) . . . . ?
C7 C6A C17 F2 -160.31(14) . . . . ?
C9B C6A C17 F1 81.6(2) . . . . ?
C6 C6A C17 F1 -162.43(14) . . . . ?
C7 C6A C17 F1 -36.8(2) . . . . ?
C9B C6A C17 F3 -160.61(14) . . . . ?
C6 C6A C17 F3 -44.65(17) . . . . ?
C7 C6A C17 F3 81.02(17) . . . . ?
C6A C9B C18 F4 79.36(19) . . . . ?
C3A C9B C18 F4 -40.6(2) . . . . ?
C9A C9B C18 F4 -163.19(14) . . . . ?
C6A C9B C18 F6 -161.18(14) . . . . ?
C3A C9B C18 F6 78.84(18) . . . . ?
C9A C9B C18 F6 -43.73(19) . . . . ?
C6A C9B C18 F5 -41.7(2) . . . . ?
C3A C9B C18 F5 -161.66(15) . . . . ?
C9A C9B C18 F5 75.78(19) . . . . ?

_refine_diff_density_max         0.406
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.079

_shelxl_version_number           2014/6


####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1570126'
_audit_update_record             
;
2017-08-22 deposited with the CCDC.
2018-01-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H10 F6 O2 S'
_chemical_formula_sum            'C14 H10 F6 O2 S'
_chemical_formula_weight         356.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0070 0.0030 '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'
O O 0.0210 0.0120 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0330 0.0200 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1970 0.2290 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.0313(16)
_cell_length_b                   7.9300(16)
_cell_length_c                   20.946(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.56(3)
_cell_angle_gamma                90
_cell_volume                     1315.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    600
_cell_measurement_theta_min      3.6
_cell_measurement_theta_max      36.0

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.799
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.763
_shelx_estimated_absorpt_T_min   0.790
_shelx_estimated_absorpt_T_max   0.852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.777
_exptl_absorpt_correction_T_max  0.848
_exptl_absorpt_process_details   'Scala (Evans, 2005)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.96990
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  'MAR CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16395
_diffrn_reflns_av_unetI/netI     0.1274
_diffrn_reflns_av_R_equivalents  0.1366
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.511
_diffrn_reflns_theta_max         38.330
_diffrn_reflns_theta_full        35.587
_diffrn_measured_fraction_theta_max 0.900
_diffrn_measured_fraction_theta_full 0.950
_diffrn_reflns_Laue_measured_fraction_max 0.900
_diffrn_reflns_Laue_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_point_group_measured_fraction_full 0.950
_reflns_number_total             2599
_reflns_number_gt                2102
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       Automar
_computing_cell_refinement       iMosflm
_computing_data_reduction        iMosflm
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.063P)²+5.65P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.052(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2599
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1032
_refine_ls_R_factor_gt           0.0887
_refine_ls_wR_factor_ref         0.2283
_refine_ls_wR_factor_gt          0.2121
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.2981(5) 0.6025(5) 0.27345(19) 0.0289(6) Uani 0.8 1 d . . P A 1
F2 F 0.4148(5) 0.3616(5) 0.26179(19) 0.0289(6) Uani 0.8 1 d . . P A 1
F3 F 0.5604(5) 0.5650(5) 0.31406(18) 0.0289(6) Uani 0.8 1 d . . P A 1
F1' F 0.268(2) 0.539(2) 0.2634(8) 0.0289(6) Uani 0.2 1 d . . P A 2
F2' F 0.488(2) 0.386(2) 0.2717(8) 0.0289(6) Uani 0.2 1 d . . P A 2
F3' F 0.510(2) 0.627(2) 0.3171(7) 0.0289(6) Uani 0.2 1 d . . P A 2
F4 F 0.0726(5) 0.3225(4) 0.27156(18) 0.0275(6) Uani 0.8 1 d . . P B 1
F5 F -0.0093(5) 0.1328(5) 0.33396(18) 0.0275(6) Uani 0.8 1 d . . P B 1
F6 F 0.2088(5) 0.0884(5) 0.28927(18) 0.0275(6) Uani 0.8 1 d . . P B 1
F4' F 0.010(2) 0.3051(18) 0.2840(8) 0.0275(6) Uani 0.2 1 d . . P B 2
F5' F 0.0437(19) 0.0713(19) 0.3350(7) 0.0275(6) Uani 0.2 1 d . . P B 2
F6' F 0.228(2) 0.1484(19) 0.2756(8) 0.0275(6) Uani 0.2 1 d . . P B 2
O1 O 0.4689(4) 0.2644(4) 0.46189(15) 0.0208(8) Uani 1 1 d . . . . .
O2 O 0.2428(4) 0.4934(4) 0.46004(15) 0.0210(7) Uani 1 1 d . . . . .
C1 C 0.0290(6) 0.2783(5) 0.4655(2) 0.0248(11) Uani 1 1 d . . . . .
H1A H -0.0514 0.2027 0.4382 0.030 Uiso 1 1 calc R U . . .
H1B H -0.0373 0.3528 0.4898 0.030 Uiso 1 1 calc R U . . .
S2 S 0.16979(15) 0.15191(13) 0.52259(6) 0.0250(4) Uani 1 1 d . . . . .
C3 C 0.2653(6) 0.0362(5) 0.4634(2) 0.0225(10) Uani 1 1 d . . . . .
H3A H 0.3479 -0.0454 0.4860 0.027 Uiso 1 1 calc R U . . .
H3B H 0.1768 -0.0282 0.4349 0.027 Uiso 1 1 calc R U . . .
C3A C 0.3544(6) 0.1536(5) 0.4219(2) 0.0208(10) Uani 1 1 d . . . . .
C4 C 0.4751(6) 0.0774(6) 0.3794(2) 0.0270(11) Uani 1 1 d . . . . .
H4 H 0.4714 -0.0331 0.3617 0.032 Uiso 1 1 calc R U . . .
C5 C 0.5849(6) 0.1984(6) 0.3727(2) 0.0274(11) Uani 1 1 d . . . . .
H5 H 0.6759 0.1927 0.3490 0.033 Uiso 1 1 calc R U . . .
C6 C 0.5348(6) 0.3486(5) 0.4109(2) 0.0231(10) Uani 1 1 d . . . . .
H6 H 0.6278 0.4305 0.4257 0.028 Uiso 1 1 calc R U . . .
C6A C 0.3684(6) 0.4293(5) 0.3702(2) 0.0212(10) Uani 1 1 d . . . . .
C7 C 0.2965(6) 0.5826(5) 0.4072(2) 0.0221(10) Uani 1 1 d . . . . .
H7 H 0.3786 0.6761 0.4203 0.027 Uiso 1 1 calc R U . . .
C8 C 0.1266(6) 0.6381(5) 0.3691(2) 0.0263(11) Uani 1 1 d . . . . .
H8 H 0.1035 0.7383 0.3443 0.032 Uiso 1 1 calc R U . . .
C9 C 0.0177(6) 0.5175(6) 0.3776(2) 0.0251(10) Uani 1 1 d . . . . .
H9 H -0.0991 0.5133 0.3599 0.030 Uiso 1 1 calc R U . . .
C9A C 0.1194(6) 0.3867(5) 0.4216(2) 0.0217(10) Uani 1 1 d . . . . .
C9B C 0.2360(6) 0.2873(5) 0.3781(2) 0.0194(9) Uani 1 1 d . . . . .
C10 C 0.4075(6) 0.4884(6) 0.3044(2) 0.0261(11) Uani 1 1 d . . . . .
C11 C 0.1306(6) 0.2084(5) 0.3184(2) 0.0221(10) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C10 1.350(6) . ?
F2 C10 1.352(6) . ?
F3 C10 1.355(6) . ?
F1' C10 1.351(18) . ?
F2' C10 1.303(16) . ?
F3' C10 1.371(16) . ?
F4 C11 1.359(6) . ?
F5 C11 1.360(6) . ?
F6 C11 1.341(5) . ?
F4' C11 1.348(16) . ?
F5' C11 1.368(15) . ?
F6' C11 1.367(15) . ?
O1 C6 1.432(5) . ?
O1 C3A 1.436(5) . ?
O2 C7 1.438(5) . ?
O2 C9A 1.443(6) . ?
C1 C9A 1.528(6) . ?
C1 S2 1.806(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
S2 C3 1.812(4) . ?
C3 C3A 1.530(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3A C4 1.544(6) . ?
C3A C9B 1.606(6) . ?
C4 C5 1.326(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.527(6) . ?
C5 H5 0.9500 . ?
C6 C6A 1.595(7) . ?
C6 H6 1.0000 . ?
C6A C10 1.536(6) . ?
C6A C9B 1.576(6) . ?
C6A C7 1.601(6) . ?
C7 C8 1.527(7) . ?
C7 H7 1.0000 . ?
C8 C9 1.327(7) . ?
C8 H8 0.9500 . ?
C9 C9A 1.531(6) . ?
C9 H9 0.9500 . ?
C9A C9B 1.616(6) . ?
C9B C11 1.525(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O1 C3A 97.5(3) . . ?
C7 O2 C9A 97.2(3) . . ?
C9A C1 S2 113.7(3) . . ?
C9A C1 H1A 108.8 . . ?
S2 C1 H1A 108.8 . . ?
C9A C1 H1B 108.8 . . ?
S2 C1 H1B 108.8 . . ?
H1A C1 H1B 107.7 . . ?
C1 S2 C3 96.7(2) . . ?
C3A C3 S2 111.8(3) . . ?
C3A C3 H3A 109.3 . . ?
S2 C3 H3A 109.3 . . ?
C3A C3 H3B 109.3 . . ?
S2 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
O1 C3A C3 110.8(4) . . ?
O1 C3A C4 100.0(3) . . ?
C3 C3A C4 119.2(3) . . ?
O1 C3A C9B 101.0(3) . . ?
C3 C3A C9B 115.9(4) . . ?
C4 C3A C9B 107.3(4) . . ?
C5 C4 C3A 105.7(4) . . ?
C5 C4 H4 127.2 . . ?
C3A C4 H4 127.2 . . ?
C4 C5 C6 105.7(4) . . ?
C4 C5 H5 127.2 . . ?
C6 C5 H5 127.2 . . ?
O1 C6 C5 100.9(3) . . ?
O1 C6 C6A 101.9(3) . . ?
C5 C6 C6A 107.6(4) . . ?
O1 C6 H6 114.9 . . ?
C5 C6 H6 114.9 . . ?
C6A C6 H6 114.9 . . ?
C10 C6A C9B 123.7(4) . . ?
C10 C6A C6 109.0(3) . . ?
C9B C6A C6 100.2(3) . . ?
C10 C6A C7 110.3(3) . . ?
C9B C6A C7 100.8(3) . . ?
C6 C6A C7 112.5(4) . . ?
O2 C7 C8 100.8(3) . . ?
O2 C7 C6A 100.2(3) . . ?
C8 C7 C6A 109.2(4) . . ?
O2 C7 H7 114.9 . . ?
C8 C7 H7 114.9 . . ?
C6A C7 H7 114.9 . . ?
C9 C8 C7 105.9(4) . . ?
C9 C8 H8 127.1 . . ?
C7 C8 H8 127.1 . . ?
C8 C9 C9A 105.8(4) . . ?
C8 C9 H9 127.1 . . ?
C9A C9 H9 127.1 . . ?
O2 C9A C1 110.2(4) . . ?
O2 C9A C9 100.8(3) . . ?
C1 C9A C9 119.0(4) . . ?
O2 C9A C9B 101.0(3) . . ?
C1 C9A C9B 116.3(3) . . ?
C9 C9A C9B 107.0(4) . . ?
C11 C9B C6A 119.9(4) . . ?
C11 C9B C3A 113.1(3) . . ?
C6A C9B C3A 100.7(3) . . ?
C11 C9B C9A 111.6(4) . . ?
C6A C9B C9A 100.1(3) . . ?
C3A C9B C9A 110.1(3) . . ?
F2' C10 F1' 106.3(10) . . ?
F1 C10 F2 106.1(4) . . ?
F1 C10 F3 105.8(4) . . ?
F2 C10 F3 107.1(4) . . ?
F2' C10 F3' 105.6(10) . . ?
F1' C10 F3' 107.0(10) . . ?
F2' C10 C6A 118.3(8) . . ?
F1 C10 C6A 115.0(4) . . ?
F1' C10 C6A 113.0(7) . . ?
F2 C10 C6A 113.8(4) . . ?
F3 C10 C6A 108.5(4) . . ?
F3' C10 C6A 106.0(7) . . ?
F6 C11 F4 106.0(4) . . ?
F6 C11 F5 105.3(4) . . ?
F4 C11 F5 105.6(4) . . ?
F4' C11 F6' 106.8(10) . . ?
F4' C11 F5' 103.6(10) . . ?
F6' C11 F5' 105.2(9) . . ?
F6 C11 C9B 115.2(4) . . ?
F4' C11 C9B 117.2(7) . . ?
F4 C11 C9B 113.3(4) . . ?
F5 C11 C9B 110.6(4) . . ?
F6' C11 C9B 112.4(8) . . ?
F5' C11 C9B 110.7(7) . . ?

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
C9A C1 S2 C3 -58.7(3) . . . . ?
C1 S2 C3 C3A 60.3(4) . . . . ?
C6 O1 C3A C3 177.6(3) . . . . ?
C6 O1 C3A C4 51.0(4) . . . . ?
C6 O1 C3A C9B -59.0(3) . . . . ?
S2 C3 C3A O1 51.6(4) . . . . ?
S2 C3 C3A C4 166.8(4) . . . . ?
S2 C3 C3A C9B -62.6(5) . . . . ?
O1 C3A C4 C5 -32.4(5) . . . . ?
C3 C3A C4 C5 -153.2(4) . . . . ?
C9B C3A C4 C5 72.5(5) . . . . ?
C3A C4 C5 C6 0.4(5) . . . . ?
C3A O1 C6 C5 -51.3(4) . . . . ?
C3A O1 C6 C6A 59.6(3) . . . . ?
C4 C5 C6 O1 32.0(5) . . . . ?
C4 C5 C6 C6A -74.3(5) . . . . ?
O1 C6 C6A C10 -166.3(3) . . . . ?
C5 C6 C6A C10 -60.6(4) . . . . ?
O1 C6 C6A C9B -35.2(4) . . . . ?
C5 C6 C6A C9B 70.5(4) . . . . ?
O1 C6 C6A C7 71.0(4) . . . . ?
C5 C6 C6A C7 176.7(3) . . . . ?
C9A O2 C7 C8 50.6(3) . . . . ?
C9A O2 C7 C6A -61.3(4) . . . . ?
C10 C6A C7 O2 170.5(4) . . . . ?
C9B C6A C7 O2 38.2(4) . . . . ?
C6 C6A C7 O2 -67.6(4) . . . . ?
C10 C6A C7 C8 65.1(5) . . . . ?
C9B C6A C7 C8 -67.2(4) . . . . ?
C6 C6A C7 C8 -173.0(3) . . . . ?
O2 C7 C8 C9 -32.5(4) . . . . ?
C6A C7 C8 C9 72.5(4) . . . . ?
C7 C8 C9 C9A 0.4(5) . . . . ?
C7 O2 C9A C1 -176.9(3) . . . . ?
C7 O2 C9A C9 -50.3(3) . . . . ?
C7 O2 C9A C9B 59.5(3) . . . . ?
S2 C1 C9A O2 -56.1(4) . . . . ?
S2 C1 C9A C9 -171.7(3) . . . . ?
S2 C1 C9A C9B 58.1(5) . . . . ?
C8 C9 C9A O2 31.6(4) . . . . ?
C8 C9 C9A C1 152.1(4) . . . . ?
C8 C9 C9A C9B -73.6(4) . . . . ?
C10 C6A C9B C11 -3.8(6) . . . . ?
C6 C6A C9B C11 -124.9(4) . . . . ?
C7 C6A C9B C11 119.6(4) . . . . ?
C10 C6A C9B C3A 120.9(4) . . . . ?
C6 C6A C9B C3A -0.1(4) . . . . ?
C7 C6A C9B C3A -115.6(3) . . . . ?
C10 C6A C9B C9A -126.1(4) . . . . ?
C6 C6A C9B C9A 112.8(4) . . . . ?
C7 C6A C9B C9A -2.7(4) . . . . ?
O1 C3A C9B C11 164.5(3) . . . . ?
C3 C3A C9B C11 -75.7(5) . . . . ?
C4 C3A C9B C11 60.3(4) . . . . ?
O1 C3A C9B C6A 35.2(4) . . . . ?
C3 C3A C9B C6A 155.0(4) . . . . ?
C4 C3A C9B C6A -69.0(4) . . . . ?
O1 C3A C9B C9A -69.8(4) . . . . ?
C3 C3A C9B C9A 50.0(5) . . . . ?
C4 C3A C9B C9A -174.1(3) . . . . ?
O2 C9A C9B C11 -161.4(3) . . . . ?
C1 C9A C9B C11 79.3(5) . . . . ?
C9 C9A C9B C11 -56.4(4) . . . . ?
O2 C9A C9B C6A -33.4(4) . . . . ?
C1 C9A C9B C6A -152.7(4) . . . . ?
C9 C9A C9B C6A 71.6(4) . . . . ?
O2 C9A C9B C3A 72.1(4) . . . . ?
C1 C9A C9B C3A -47.2(5) . . . . ?
C9 C9A C9B C3A 177.1(3) . . . . ?
C9B C6A C10 F2' -69.9(10) . . . . ?
C6 C6A C10 F2' 47.0(10) . . . . ?
C7 C6A C10 F2' 171.0(9) . . . . ?
C9B C6A C10 F1 82.3(5) . . . . ?
C6 C6A C10 F1 -160.7(4) . . . . ?
C7 C6A C10 F1 -36.8(5) . . . . ?
C9B C6A C10 F1' 55.1(9) . . . . ?
C6 C6A C10 F1' 172.0(8) . . . . ?
C7 C6A C10 F1' -64.0(9) . . . . ?
C9B C6A C10 F2 -40.3(6) . . . . ?
C6 C6A C10 F2 76.6(5) . . . . ?
C7 C6A C10 F2 -159.4(4) . . . . ?
C9B C6A C10 F3 -159.4(4) . . . . ?
C6 C6A C10 F3 -42.5(5) . . . . ?
C7 C6A C10 F3 81.5(4) . . . . ?
C9B C6A C10 F3' 172.0(8) . . . . ?
C6 C6A C10 F3' -71.1(8) . . . . ?
C7 C6A C10 F3' 52.9(8) . . . . ?
C6A C9B C11 F6 80.5(5) . . . . ?
C3A C9B C11 F6 -38.1(5) . . . . ?
C9A C9B C11 F6 -163.0(4) . . . . ?
C6A C9B C11 F4' -70.9(9) . . . . ?
C3A C9B C11 F4' 170.4(8) . . . . ?
C9A C9B C11 F4' 45.6(9) . . . . ?
C6A C9B C11 F4 -41.8(5) . . . . ?
C3A C9B C11 F4 -160.5(4) . . . . ?
C9A C9B C11 F4 74.7(4) . . . . ?
C6A C9B C11 F5 -160.2(4) . . . . ?
C3A C9B C11 F5 81.2(4) . . . . ?
C9A C9B C11 F5 -43.7(5) . . . . ?
C6A C9B C11 F6' 53.3(8) . . . . ?
C3A C9B C11 F6' -65.4(8) . . . . ?
C9A C9B C11 F6' 169.7(8) . . . . ?
C6A C9B C11 F5' 170.6(8) . . . . ?
C3A C9B C11 F5' 51.9(8) . . . . ?
C9A C9B C11 F5' -73.0(8) . . . . ?

_refine_diff_density_max         0.590
_refine_diff_density_min         -0.640
_refine_diff_density_rms         0.141

_shelxl_version_number           2014/6


####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1570125'
_audit_update_record             
;
2017-08-22 deposited with the CCDC.
2018-01-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H10 F9 N O3, 0.5(C4 H8 O2)'
_chemical_formula_sum            'C18 H14 F9 N O4'
_chemical_formula_weight         479.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0070 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0130 0.0070 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0210 0.0120 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0330 0.0200 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   10.190(2)
_cell_length_b                   12.170(2)
_cell_length_c                   15.440(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.72(3)
_cell_angle_gamma                90
_cell_volume                     1851.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    500
_cell_measurement_theta_min      3.6
_cell_measurement_theta_max      36.0

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.719
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.404
_shelx_estimated_absorpt_T_min   0.898
_shelx_estimated_absorpt_T_max   0.937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.890
_exptl_absorpt_correction_T_max  0.930
_exptl_absorpt_process_details   'Scala (Evans, 2005)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.96990
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  'MAR CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23131
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.630
_diffrn_reflns_theta_max         38.415
_diffrn_reflns_theta_full        35.587
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             3791
_reflns_number_gt                3350
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       Automar
_computing_cell_refinement       iMosflm
_computing_data_reduction        iMosflm
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0449P)²+0.9139P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0108(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3791
_refine_ls_number_parameters     317
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.1037
_refine_ls_wR_factor_gt          0.0982
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.06331(9) 0.77344(8) 0.23741(7) 0.0297(3) Uani 1 1 d . . . . .
F2 F 0.12766(10) 0.85017(9) 0.36840(7) 0.0318(3) Uani 1 1 d . . . . .
F3 F -0.00492(9) 0.93702(9) 0.25851(8) 0.0377(3) Uani 1 1 d . . . . .
F4 F 0.91887(9) 0.83904(8) 0.47344(7) 0.0291(2) Uani 1 1 d . . . . .
F5 F 0.85199(10) 0.72214(8) 0.55767(7) 0.0323(3) Uani 1 1 d . . . . .
F6 F 0.86844(10) 0.89330(9) 0.59439(7) 0.0342(3) Uani 1 1 d . . . . .
F7 F 0.61265(9) 0.68701(8) 0.25632(7) 0.0282(2) Uani 1 1 d . . . . .
F8 F 0.77009(9) 0.65970(8) 0.37767(7) 0.0284(2) Uani 1 1 d . . . . .
F9 F 0.78570(9) 0.79428(8) 0.29097(7) 0.0276(2) Uani 1 1 d . . . . .
O1 O 0.45336(10) 0.81020(8) 0.45994(7) 0.0186(2) Uani 1 1 d . . . . .
O2 O 0.53340(10) 0.98475(8) 0.39822(7) 0.0170(2) Uani 1 1 d . . . . .
O3 O 0.20527(12) 1.01321(9) 0.21770(9) 0.0293(3) Uani 1 1 d . . . . .
C1 C 0.45727(14) 0.91871(12) 0.24533(10) 0.0192(3) Uani 1 1 d . . . . .
H1A H 0.4310 0.9931 0.2211 0.023 Uiso 1 1 calc R U . . .
H1B H 0.4852 0.8754 0.1988 0.023 Uiso 1 1 calc R U . . .
N2 N 0.34049(12) 0.86519(10) 0.26827(9) 0.0179(3) Uani 1 1 d . . . . .
C3 C 0.36359(14) 0.75285(12) 0.30545(11) 0.0190(3) Uani 1 1 d . . . . .
H3A H 0.3807 0.7025 0.2592 0.023 Uiso 1 1 calc R U . . .
H3B H 0.2812 0.7271 0.3222 0.023 Uiso 1 1 calc R U . . .
C3A C 0.48361(14) 0.74977(11) 0.38719(10) 0.0168(3) Uani 1 1 d . . . . .
C4 C 0.52988(14) 0.63989(12) 0.43347(11) 0.0202(3) Uani 1 1 d . . . . .
H4 H 0.5177 0.5686 0.4076 0.024 Uiso 1 1 calc R U . . .
C5 C 0.59094(15) 0.66600(12) 0.51802(11) 0.0228(3) Uani 1 1 d . . . . .
H5 H 0.6327 0.6170 0.5648 0.027 Uiso 1 1 calc R U . . .
C6 C 0.57996(15) 0.79153(12) 0.52420(10) 0.0203(3) Uani 1 1 d . . . . .
H6 H 0.5847 0.8203 0.5856 0.024 Uiso 1 1 calc R U . . .
C6A C 0.68221(14) 0.84823(12) 0.47513(10) 0.0171(3) Uani 1 1 d . . . . .
C7 C 0.66158(14) 0.97811(12) 0.46424(10) 0.0187(3) Uani 1 1 d . . . . .
H7 H 0.6655 1.0187 0.5212 0.022 Uiso 1 1 calc R U . . .
C8 C 0.75694(15) 1.02175(12) 0.40986(11) 0.0223(3) Uani 1 1 d . . . . .
H8 H 0.8381 1.0625 0.4319 0.027 Uiso 1 1 calc R U . . .
C9 C 0.70292(14) 0.99105(12) 0.32539(11) 0.0203(3) Uani 1 1 d . . . . .
H9 H 0.7368 1.0057 0.2746 0.024 Uiso 1 1 calc R U . . .
C9A C 0.57437(14) 0.92702(11) 0.32797(10) 0.0162(3) Uani 1 1 d . . . . .
C9B C 0.61707(13) 0.81154(11) 0.37541(10) 0.0152(3) Uani 1 1 d . . . . .
C10 C 0.22366(14) 0.92232(12) 0.25304(10) 0.0194(3) Uani 1 1 d . . . . .
C11 C 0.10094(15) 0.86954(13) 0.27994(11) 0.0236(3) Uani 1 1 d . . . . .
C12 C 0.82997(15) 0.82437(13) 0.52342(11) 0.0229(3) Uani 1 1 d . . . . .
C13 C 0.69781(14) 0.73920(12) 0.32593(10) 0.0197(3) Uani 1 1 d . . . . .
O4 O 0.8999(3) 0.4483(2) 0.39952(16) 0.0376(6) Uani 0.5 1 d D . P . .
O5 O 1.0152(2) 0.51602(19) 0.53415(17) 0.0271(5) Uani 0.5 1 d D . P . .
C14 C 0.9197(4) 0.4519(3) 0.47962(18) 0.0235(8) Uani 0.5 1 d D . P . .
C15 C 0.8391(4) 0.3905(3) 0.5329(3) 0.0388(9) Uani 0.5 1 d D . P . .
H15A H 0.7812 0.3444 0.4865 0.058 Uiso 0.5 1 d R U P . .
H15B H 0.7829 0.4444 0.5541 0.058 Uiso 0.5 1 d R U P . .
H15C H 0.8867 0.3442 0.5830 0.058 Uiso 0.5 1 d R U P . .
C16 C 1.1020(4) 0.5755(3) 0.4889(2) 0.0266(9) Uani 0.5 1 d D . P . .
H16A H 1.0472 0.6244 0.4422 0.032 Uiso 0.5 1 d R U P . .
H16B H 1.1521 0.5233 0.4600 0.032 Uiso 0.5 1 d R U P . .
C17 C 1.2011(3) 0.6423(3) 0.5595(2) 0.0364(8) Uani 0.5 1 d D . P . .
H17A H 1.2618 0.6835 0.5313 0.055 Uiso 0.5 1 d R U P . .
H17B H 1.1503 0.6937 0.5875 0.055 Uiso 0.5 1 d R U P . .
H17C H 1.2547 0.5930 0.6052 0.055 Uiso 0.5 1 d R U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C11 1.3484(19) . ?
F2 C11 1.344(2) . ?
F3 C11 1.3289(18) . ?
F4 C12 1.3428(19) . ?
F5 C12 1.3481(19) . ?
F6 C12 1.3564(19) . ?
F7 C13 1.3556(18) . ?
F8 C13 1.3481(18) . ?
F9 C13 1.3373(17) . ?
O1 C6 1.4317(19) . ?
O1 C3A 1.4400(18) . ?
O2 C9A 1.4403(17) . ?
O2 C7 1.4404(18) . ?
O3 C10 1.2265(19) . ?
C1 N2 1.4764(18) . ?
C1 C9A 1.513(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
N2 C10 1.3467(19) . ?
N2 C3 1.4784(18) . ?
C3 C3A 1.518(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3A C4 1.533(2) . ?
C3A C9B 1.6042(19) . ?
C4 C5 1.334(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.537(2) . ?
C5 H5 0.9500 . ?
C6 C6A 1.593(2) . ?
C6 H6 1.0000 . ?
C6A C12 1.529(2) . ?
C6A C9B 1.578(2) . ?
C6A C7 1.598(2) . ?
C7 C8 1.532(2) . ?
C7 H7 1.0000 . ?
C8 C9 1.334(2) . ?
C8 H8 0.9500 . ?
C9 C9A 1.5334(19) . ?
C9 H9 0.9500 . ?
C9A C9B 1.5935(19) . ?
C9B C13 1.5346(19) . ?
C10 C11 1.553(2) . ?
O4 C14 1.202(3) . ?
O5 C14 1.359(3) . ?
O5 C16 1.452(3) . ?
C14 C15 1.501(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9799 . ?
C15 H15C 0.9799 . ?
C16 C17 1.520(3) . ?
C16 H16A 0.9901 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9801 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9798 . ?

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
C6 O1 C3A 97.23(10) . . ?
C9A O2 C7 96.97(10) . . ?
N2 C1 C9A 109.77(12) . . ?
N2 C1 H1A 109.7 . . ?
C9A C1 H1A 109.7 . . ?
N2 C1 H1B 109.7 . . ?
C9A C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
C10 N2 C1 117.45(12) . . ?
C10 N2 C3 126.28(12) . . ?
C1 N2 C3 116.27(11) . . ?
N2 C3 C3A 111.14(12) . . ?
N2 C3 H3A 109.4 . . ?
C3A C3 H3A 109.4 . . ?
N2 C3 H3B 109.4 . . ?
C3A C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
O1 C3A C3 110.42(11) . . ?
O1 C3A C4 100.56(11) . . ?
C3 C3A C4 119.76(12) . . ?
O1 C3A C9B 101.81(11) . . ?
C3 C3A C9B 114.91(12) . . ?
C4 C3A C9B 107.00(11) . . ?
C5 C4 C3A 105.07(13) . . ?
C5 C4 H4 127.5 . . ?
C3A C4 H4 127.5 . . ?
C4 C5 C6 105.93(13) . . ?
C4 C5 H5 127.0 . . ?
C6 C5 H5 127.0 . . ?
O1 C6 C5 100.47(12) . . ?
O1 C6 C6A 100.65(11) . . ?
C5 C6 C6A 109.53(12) . . ?
O1 C6 H6 114.8 . . ?
C5 C6 H6 114.8 . . ?
C6A C6 H6 114.8 . . ?
C12 C6A C9B 122.68(12) . . ?
C12 C6A C6 111.60(12) . . ?
C9B C6A C6 100.24(11) . . ?
C12 C6A C7 109.04(11) . . ?
C9B C6A C7 99.54(11) . . ?
C6 C6A C7 113.21(11) . . ?
O2 C7 C8 100.38(12) . . ?
O2 C7 C6A 101.62(10) . . ?
C8 C7 C6A 108.42(12) . . ?
O2 C7 H7 114.9 . . ?
C8 C7 H7 114.9 . . ?
C6A C7 H7 114.9 . . ?
C9 C8 C7 106.09(13) . . ?
C9 C8 H8 127.0 . . ?
C7 C8 H8 127.0 . . ?
C8 C9 C9A 105.07(13) . . ?
C8 C9 H9 127.5 . . ?
C9A C9 H9 127.5 . . ?
O2 C9A C1 110.51(11) . . ?
O2 C9A C9 100.64(11) . . ?
C1 C9A C9 120.53(13) . . ?
O2 C9A C9B 100.46(11) . . ?
C1 C9A C9B 113.17(11) . . ?
C9 C9A C9B 108.96(11) . . ?
C13 C9B C6A 120.14(12) . . ?
C13 C9B C9A 113.29(12) . . ?
C6A C9B C9A 101.36(11) . . ?
C13 C9B C3A 111.39(11) . . ?
C6A C9B C3A 100.40(11) . . ?
C9A C9B C3A 108.97(10) . . ?
O3 C10 N2 124.86(14) . . ?
O3 C10 C11 116.71(13) . . ?
N2 C10 C11 118.41(13) . . ?
F3 C11 F2 107.67(13) . . ?
F3 C11 F1 107.60(12) . . ?
F2 C11 F1 107.57(13) . . ?
F3 C11 C10 109.61(13) . . ?
F2 C11 C10 112.04(13) . . ?
F1 C11 C10 112.15(12) . . ?
F4 C12 F5 106.19(12) . . ?
F4 C12 F6 106.46(12) . . ?
F5 C12 F6 105.59(13) . . ?
F4 C12 C6A 114.78(13) . . ?
F5 C12 C6A 114.31(12) . . ?
F6 C12 C6A 108.85(12) . . ?
F9 C13 F8 106.13(11) . . ?
F9 C13 F7 105.92(12) . . ?
F8 C13 F7 106.07(12) . . ?
F9 C13 C9B 114.33(12) . . ?
F8 C13 C9B 113.45(12) . . ?
F7 C13 C9B 110.32(11) . . ?
C14 O5 C16 114.6(3) . . ?
O4 C14 O5 124.4(4) . . ?
O4 C14 C15 125.0(3) . . ?
O5 C14 C15 110.6(3) . . ?
C14 C15 H15A 101.4 . . ?
C14 C15 H15B 107.3 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 119.3 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O5 C16 C17 107.2(3) . . ?
O5 C16 H16A 110.5 . . ?
C17 C16 H16A 110.5 . . ?
O5 C16 H16B 110.2 . . ?
C17 C16 H16B 110.0 . . ?
H16A C16 H16B 108.5 . . ?
C16 C17 H17A 109.6 . . ?
C16 C17 H17B 109.2 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.7 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C9A C1 N2 C10 120.97(14) . . . . ?
C9A C1 N2 C3 -59.45(16) . . . . ?
C10 N2 C3 C3A -125.26(15) . . . . ?
C1 N2 C3 C3A 55.20(17) . . . . ?
C6 O1 C3A C3 179.43(11) . . . . ?
C6 O1 C3A C4 51.97(12) . . . . ?
C6 O1 C3A C9B -58.08(12) . . . . ?
N2 C3 C3A O1 67.12(15) . . . . ?
N2 C3 C3A C4 -176.89(12) . . . . ?
N2 C3 C3A C9B -47.33(16) . . . . ?
O1 C3A C4 C5 -33.26(14) . . . . ?
C3 C3A C4 C5 -154.30(14) . . . . ?
C9B C3A C4 C5 72.69(15) . . . . ?
C3A C4 C5 C6 1.01(15) . . . . ?
C3A O1 C6 C5 -51.11(12) . . . . ?
C3A O1 C6 C6A 61.27(12) . . . . ?
C4 C5 C6 O1 31.72(15) . . . . ?
C4 C5 C6 C6A -73.64(15) . . . . ?
O1 C6 C6A C12 -170.99(11) . . . . ?
C5 C6 C6A C12 -65.75(16) . . . . ?
O1 C6 C6A C9B -39.57(12) . . . . ?
C5 C6 C6A C9B 65.67(14) . . . . ?
O1 C6 C6A C7 65.54(14) . . . . ?
C5 C6 C6A C7 170.78(12) . . . . ?
C9A O2 C7 C8 51.25(12) . . . . ?
C9A O2 C7 C6A -60.20(12) . . . . ?
C12 C6A C7 O2 164.85(12) . . . . ?
C9B C6A C7 O2 35.26(12) . . . . ?
C6 C6A C7 O2 -70.29(14) . . . . ?
C12 C6A C7 C8 59.64(16) . . . . ?
C9B C6A C7 C8 -69.95(13) . . . . ?
C6 C6A C7 C8 -175.50(12) . . . . ?
O2 C7 C8 C9 -32.06(14) . . . . ?
C6A C7 C8 C9 74.01(15) . . . . ?
C7 C8 C9 C9A -0.61(15) . . . . ?
C7 O2 C9A C1 179.66(11) . . . . ?
C7 O2 C9A C9 -51.86(12) . . . . ?
C7 O2 C9A C9B 59.91(11) . . . . ?
N2 C1 C9A O2 -56.26(15) . . . . ?
N2 C1 C9A C9 -172.97(12) . . . . ?
N2 C1 C9A C9B 55.51(15) . . . . ?
C8 C9 C9A O2 33.15(14) . . . . ?
C8 C9 C9A C1 154.80(14) . . . . ?
C8 C9 C9A C9B -71.91(15) . . . . ?
C12 C6A C9B C13 6.2(2) . . . . ?
C6 C6A C9B C13 -117.83(13) . . . . ?
C7 C6A C9B C13 126.29(13) . . . . ?
C12 C6A C9B C9A -119.43(14) . . . . ?
C6 C6A C9B C9A 116.50(11) . . . . ?
C7 C6A C9B C9A 0.62(12) . . . . ?
C12 C6A C9B C3A 128.61(13) . . . . ?
C6 C6A C9B C3A 4.54(12) . . . . ?
C7 C6A C9B C3A -111.34(11) . . . . ?
O2 C9A C9B C13 -166.32(11) . . . . ?
C1 C9A C9B C13 75.87(15) . . . . ?
C9 C9A C9B C13 -61.13(15) . . . . ?
O2 C9A C9B C6A -36.21(12) . . . . ?
C1 C9A C9B C6A -154.03(12) . . . . ?
C9 C9A C9B C6A 68.97(14) . . . . ?
O2 C9A C9B C3A 69.07(13) . . . . ?
C1 C9A C9B C3A -48.74(15) . . . . ?
C9 C9A C9B C3A 174.26(11) . . . . ?
O1 C3A C9B C13 159.69(11) . . . . ?
C3 C3A C9B C13 -80.95(15) . . . . ?
C4 C3A C9B C13 54.63(15) . . . . ?
O1 C3A C9B C6A 31.36(12) . . . . ?
C3 C3A C9B C6A 150.72(12) . . . . ?
C4 C3A C9B C6A -73.70(13) . . . . ?
O1 C3A C9B C9A -74.59(13) . . . . ?
C3 C3A C9B C9A 44.77(15) . . . . ?
C4 C3A C9B C9A -179.65(11) . . . . ?
C1 N2 C10 O3 3.6(2) . . . . ?
C3 N2 C10 O3 -175.93(14) . . . . ?
C1 N2 C10 C11 -177.73(13) . . . . ?
C3 N2 C10 C11 2.7(2) . . . . ?
O3 C10 C11 F3 -0.2(2) . . . . ?
N2 C10 C11 F3 -179.00(13) . . . . ?
O3 C10 C11 F2 -119.70(15) . . . . ?
N2 C10 C11 F2 61.54(18) . . . . ?
O3 C10 C11 F1 119.21(15) . . . . ?
N2 C10 C11 F1 -59.56(18) . . . . ?
C9B C6A C12 F4 41.60(19) . . . . ?
C6 C6A C12 F4 160.36(12) . . . . ?
C7 C6A C12 F4 -73.84(16) . . . . ?
C9B C6A C12 F5 -81.46(18) . . . . ?
C6 C6A C12 F5 37.30(17) . . . . ?
C7 C6A C12 F5 163.10(13) . . . . ?
C9B C6A C12 F6 160.77(13) . . . . ?
C6 C6A C12 F6 -80.48(15) . . . . ?
C7 C6A C12 F6 45.33(16) . . . . ?
C6A C9B C13 F9 -81.70(16) . . . . ?
C9A C9B C13 F9 38.17(17) . . . . ?
C3A C9B C13 F9 161.45(12) . . . . ?
C6A C9B C13 F8 40.21(18) . . . . ?
C9A C9B C13 F8 160.08(11) . . . . ?
C3A C9B C13 F8 -76.64(15) . . . . ?
C6A C9B C13 F7 159.05(12) . . . . ?
C9A C9B C13 F7 -81.08(15) . . . . ?
C3A C9B C13 F7 42.21(16) . . . . ?
C16 O5 C14 O4 -4.9(6) . . . . ?
C16 O5 C14 C15 177.7(3) . . . . ?
C14 O5 C16 C17 179.9(3) . . . . ?

_refine_diff_density_max         0.377
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.057

_shelxl_version_number           2014/6


####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1570127'
_audit_update_record             
;
2017-08-22 deposited with the CCDC.
2018-01-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H10 F6 O2 S'
_chemical_formula_sum            'C14 H10 F6 O2 S'
_chemical_formula_weight         356.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0070 0.0030 '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'
O O 0.0210 0.0120 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0330 0.0200 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1970 0.2290 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   5.3500(11)
_cell_length_b                   9.6550(19)
_cell_length_c                   13.985(3)
_cell_angle_alpha                97.81(3)
_cell_angle_beta                 98.93(3)
_cell_angle_gamma                102.32(3)
_cell_volume                     686.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    600
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      33.0

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.731
_shelx_estimated_absorpt_T_min   0.810
_shelx_estimated_absorpt_T_max   0.867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.800
_exptl_absorpt_correction_T_max  0.850
_exptl_absorpt_process_details   'Scala (Evans, 2005)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.96990
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  'MAR CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13089
_diffrn_reflns_av_unetI/netI     0.1176
_diffrn_reflns_av_R_equivalents  0.1246
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.316
_diffrn_reflns_theta_max         38.490
_diffrn_reflns_theta_full        35.587
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.925
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             2813
_reflns_number_gt                2348
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       Automar
_computing_cell_refinement       iMosflm
_computing_data_reduction        iMosflm
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0406P)²+1.4P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.115(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2813
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0710
_refine_ls_wR_factor_ref         0.1835
_refine_ls_wR_factor_gt          0.1736
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.8812(4) 0.4895(2) 0.23946(16) 0.0346(5) Uani 1 1 d . . . . .
F2 F 0.5265(5) 0.3766(2) 0.27520(18) 0.0395(6) Uani 1 1 d . . . . .
F3 F 0.8538(5) 0.4800(3) 0.39135(16) 0.0463(7) Uani 1 1 d . . . . .
F4 F 0.6853(5) 0.6326(2) 0.53439(15) 0.0421(6) Uani 1 1 d . . . . .
F5 F 0.6745(5) 0.8559(3) 0.54593(15) 0.0443(7) Uani 1 1 d . . . . .
F6 F 1.0105(4) 0.7876(3) 0.50887(15) 0.0395(6) Uani 1 1 d . . . . .
O1 O 0.3337(4) 0.7581(2) 0.25748(16) 0.0219(5) Uani 1 1 d . . . . .
O2 O 0.4983(5) 0.9719(2) 0.15292(17) 0.0257(6) Uani 1 1 d . . . . .
C1 C 0.5559(7) 0.7926(4) 0.0207(2) 0.0269(7) Uani 1 1 d . . . . .
H1A H 0.6837 0.7399 0.0000 0.032 Uiso 1 1 calc R U . . .
H1B H 0.5178 0.8527 -0.0292 0.032 Uiso 1 1 calc R U . . .
S2 S 0.25680(16) 0.66328(9) 0.02503(6) 0.0264(3) Uani 1 1 d . . . . .
C3 C 0.3835(7) 0.5775(3) 0.1242(2) 0.0241(7) Uani 1 1 d . . . . .
H3A H 0.2387 0.5051 0.1382 0.029 Uiso 1 1 calc R U . . .
H3B H 0.5122 0.5263 0.1024 0.029 Uiso 1 1 calc R U . . .
C3A C 0.5116(6) 0.6841(3) 0.2175(2) 0.0203(7) Uani 1 1 d . . . . .
C4 C 0.6241(6) 0.6283(3) 0.3100(2) 0.0217(7) Uani 1 1 d . . . . .
C5 C 0.6264(7) 0.7289(3) 0.3866(2) 0.0231(7) Uani 1 1 d . . . . .
C6 C 0.5145(7) 0.8449(3) 0.3416(2) 0.0236(7) Uani 1 1 d . . . . .
H6 H 0.4384 0.9063 0.3869 0.028 Uiso 1 1 calc R U . . .
C6A C 0.7378(7) 0.9282(3) 0.2966(2) 0.0229(7) Uani 1 1 d . . . . .
H6A H 0.9084 0.9586 0.3437 0.028 Uiso 1 1 calc R U . . .
C7 C 0.6747(7) 1.0517(4) 0.2423(3) 0.0284(8) Uani 1 1 d . . . . .
H7 H 0.6083 1.1258 0.2814 0.034 Uiso 1 1 calc R U . . .
C8 C 0.9190(8) 1.1093(4) 0.2028(3) 0.0338(8) Uani 1 1 d . . . . .
H8 H 1.0442 1.1980 0.2270 0.041 Uiso 1 1 calc R U . . .
C9 C 0.9205(7) 1.0093(4) 0.1270(3) 0.0298(8) Uani 1 1 d . . . . .
H9 H 1.0477 1.0118 0.0864 0.036 Uiso 1 1 calc R U . . .
C9A C 0.6753(7) 0.8897(3) 0.1191(2) 0.0233(7) Uani 1 1 d . . . . .
C9B C 0.7384(6) 0.8115(3) 0.2073(2) 0.0213(7) Uani 1 1 d . . . . .
H9B H 0.9092 0.7842 0.2106 0.026 Uiso 1 1 calc R U . . .
C10 C 0.7252(7) 0.4954(3) 0.3053(2) 0.0259(7) Uani 1 1 d . . . . .
C11 C 0.7474(8) 0.7477(4) 0.4934(2) 0.0298(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C10 1.338(4) . ?
F2 C10 1.353(4) . ?
F3 C10 1.334(4) . ?
F4 C11 1.322(4) . ?
F5 C11 1.356(4) . ?
F6 C11 1.352(5) . ?
O1 C6 1.433(4) . ?
O1 C3A 1.441(4) . ?
O2 C9A 1.452(4) . ?
O2 C7 1.452(4) . ?
C1 C9A 1.517(5) . ?
C1 S2 1.822(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
S2 C3 1.824(3) . ?
C3 C3A 1.513(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3A C4 1.553(4) . ?
C3A C9B 1.572(4) . ?
C4 C5 1.341(4) . ?
C4 C10 1.493(4) . ?
C5 C11 1.503(5) . ?
C5 C6 1.539(4) . ?
C6 C6A 1.559(5) . ?
C6 H6 1.0000 . ?
C6A C9B 1.565(4) . ?
C6A C7 1.565(5) . ?
C6A H6A 1.0000 . ?
C7 C8 1.523(5) . ?
C7 H7 1.0000 . ?
C8 C9 1.336(5) . ?
C8 H8 0.9500 . ?
C9 C9A 1.530(5) . ?
C9 H9 0.9500 . ?
C9A C9B 1.561(4) . ?
C9B H9B 1.0000 . ?

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
C6 O1 C3A 97.5(2) . . ?
C9A O2 C7 96.4(2) . . ?
C9A C1 S2 112.5(2) . . ?
C9A C1 H1A 109.1 . . ?
S2 C1 H1A 109.1 . . ?
C9A C1 H1B 109.1 . . ?
S2 C1 H1B 109.1 . . ?
H1A C1 H1B 107.8 . . ?
C1 S2 C3 98.85(16) . . ?
C3A C3 S2 112.6(2) . . ?
C3A C3 H3A 109.1 . . ?
S2 C3 H3A 109.1 . . ?
C3A C3 H3B 109.1 . . ?
S2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
O1 C3A C3 112.8(3) . . ?
O1 C3A C4 99.8(2) . . ?
C3 C3A C4 119.3(3) . . ?
O1 C3A C9B 102.7(2) . . ?
C3 C3A C9B 115.9(3) . . ?
C4 C3A C9B 104.0(2) . . ?
C5 C4 C10 131.0(3) . . ?
C5 C4 C3A 105.4(3) . . ?
C10 C4 C3A 123.4(3) . . ?
C4 C5 C11 130.7(3) . . ?
C4 C5 C6 105.4(3) . . ?
C11 C5 C6 123.2(3) . . ?
O1 C6 C5 100.7(2) . . ?
O1 C6 C6A 103.7(2) . . ?
C5 C6 C6A 105.0(3) . . ?
O1 C6 H6 115.2 . . ?
C5 C6 H6 115.2 . . ?
C6A C6 H6 115.2 . . ?
C6 C6A C9B 100.4(2) . . ?
C6 C6A C7 116.3(3) . . ?
C9B C6A C7 100.8(2) . . ?
C6 C6A H6A 112.7 . . ?
C9B C6A H6A 112.7 . . ?
C7 C6A H6A 112.7 . . ?
O2 C7 C8 101.4(3) . . ?
O2 C7 C6A 102.2(2) . . ?
C8 C7 C6A 105.1(3) . . ?
O2 C7 H7 115.4 . . ?
C8 C7 H7 115.4 . . ?
C6A C7 H7 115.4 . . ?
C9 C8 C7 105.7(3) . . ?
C9 C8 H8 127.2 . . ?
C7 C8 H8 127.2 . . ?
C8 C9 C9A 105.8(3) . . ?
C8 C9 H9 127.1 . . ?
C9A C9 H9 127.1 . . ?
O2 C9A C1 111.8(3) . . ?
O2 C9A C9 101.1(3) . . ?
C1 C9A C9 119.2(3) . . ?
O2 C9A C9B 102.1(2) . . ?
C1 C9A C9B 115.8(3) . . ?
C9 C9A C9B 104.6(3) . . ?
C9A C9B C6A 101.4(2) . . ?
C9A C9B C3A 114.9(3) . . ?
C6A C9B C3A 101.5(2) . . ?
C9A C9B H9B 112.6 . . ?
C6A C9B H9B 112.6 . . ?
C3A C9B H9B 112.6 . . ?
F3 C10 F1 108.2(3) . . ?
F3 C10 F2 106.4(3) . . ?
F1 C10 F2 105.6(3) . . ?
F3 C10 C4 113.8(3) . . ?
F1 C10 C4 111.9(3) . . ?
F2 C10 C4 110.5(3) . . ?
F4 C11 F6 107.0(3) . . ?
F4 C11 F5 107.1(3) . . ?
F6 C11 F5 105.4(3) . . ?
F4 C11 C5 114.9(3) . . ?
F6 C11 C5 112.1(3) . . ?
F5 C11 C5 109.8(3) . . ?

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
C9A C1 S2 C3 -56.3(3) . . . . ?
C1 S2 C3 C3A 56.1(3) . . . . ?
C6 O1 C3A C3 179.6(2) . . . . ?
C6 O1 C3A C4 52.0(3) . . . . ?
C6 O1 C3A C9B -55.0(3) . . . . ?
S2 C3 C3A O1 62.0(3) . . . . ?
S2 C3 C3A C4 178.6(2) . . . . ?
S2 C3 C3A C9B -56.0(3) . . . . ?
O1 C3A C4 C5 -32.8(3) . . . . ?
C3 C3A C4 C5 -156.1(3) . . . . ?
C9B C3A C4 C5 73.0(3) . . . . ?
O1 C3A C4 C10 152.0(3) . . . . ?
C3 C3A C4 C10 28.8(5) . . . . ?
C9B C3A C4 C10 -102.1(3) . . . . ?
C10 C4 C5 C11 4.6(6) . . . . ?
C3A C4 C5 C11 -170.0(3) . . . . ?
C10 C4 C5 C6 175.0(3) . . . . ?
C3A C4 C5 C6 0.4(3) . . . . ?
C3A O1 C6 C5 -52.2(3) . . . . ?
C3A O1 C6 C6A 56.3(3) . . . . ?
C4 C5 C6 O1 32.4(3) . . . . ?
C11 C5 C6 O1 -156.2(3) . . . . ?
C4 C5 C6 C6A -75.0(3) . . . . ?
C11 C5 C6 C6A 96.3(4) . . . . ?
O1 C6 C6A C9B -34.6(3) . . . . ?
C5 C6 C6A C9B 70.7(3) . . . . ?
O1 C6 C6A C7 73.0(3) . . . . ?
C5 C6 C6A C7 178.3(3) . . . . ?
C9A O2 C7 C8 50.6(3) . . . . ?
C9A O2 C7 C6A -57.8(3) . . . . ?
C6 C6A C7 O2 -72.3(3) . . . . ?
C9B C6A C7 O2 35.1(3) . . . . ?
C6 C6A C7 C8 -177.8(3) . . . . ?
C9B C6A C7 C8 -70.4(3) . . . . ?
O2 C7 C8 C9 -32.6(3) . . . . ?
C6A C7 C8 C9 73.5(3) . . . . ?
C7 C8 C9 C9A 0.4(4) . . . . ?
C7 O2 C9A C1 -178.0(3) . . . . ?
C7 O2 C9A C9 -50.2(3) . . . . ?
C7 O2 C9A C9B 57.6(3) . . . . ?
S2 C1 C9A O2 -59.7(3) . . . . ?
S2 C1 C9A C9 -177.1(2) . . . . ?
S2 C1 C9A C9B 56.7(3) . . . . ?
C8 C9 C9A O2 31.9(3) . . . . ?
C8 C9 C9A C1 154.8(3) . . . . ?
C8 C9 C9A C9B -73.8(3) . . . . ?
O2 C9A C9B C6A -34.9(3) . . . . ?
C1 C9A C9B C6A -156.6(3) . . . . ?
C9 C9A C9B C6A 70.1(3) . . . . ?
O2 C9A C9B C3A 73.6(3) . . . . ?
C1 C9A C9B C3A -48.0(4) . . . . ?
C9 C9A C9B C3A 178.7(3) . . . . ?
C6 C6A C9B C9A 119.4(3) . . . . ?
C7 C6A C9B C9A -0.1(3) . . . . ?
C6 C6A C9B C3A 0.8(3) . . . . ?
C7 C6A C9B C3A -118.8(3) . . . . ?
O1 C3A C9B C9A -75.7(3) . . . . ?
C3 C3A C9B C9A 47.7(4) . . . . ?
C4 C3A C9B C9A -179.3(2) . . . . ?
O1 C3A C9B C6A 32.8(3) . . . . ?
C3 C3A C9B C6A 156.2(3) . . . . ?
C4 C3A C9B C6A -70.9(3) . . . . ?
C5 C4 C10 F3 -4.8(5) . . . . ?
C3A C4 C10 F3 168.9(3) . . . . ?
C5 C4 C10 F1 -127.9(4) . . . . ?
C3A C4 C10 F1 45.9(4) . . . . ?
C5 C4 C10 F2 114.8(4) . . . . ?
C3A C4 C10 F2 -71.5(4) . . . . ?
C4 C5 C11 F4 -52.3(5) . . . . ?
C6 C5 C11 F4 138.7(3) . . . . ?
C4 C5 C11 F6 70.1(5) . . . . ?
C6 C5 C11 F6 -98.9(4) . . . . ?
C4 C5 C11 F5 -173.1(3) . . . . ?
C6 C5 C11 F5 17.9(5) . . . . ?

_refine_diff_density_max         0.539
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.110

_shelxl_version_number           2014/6


####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1570128'
_audit_update_record             
;
2017-08-22 deposited with the CCDC.
2018-01-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H10 F9 N O3'
_chemical_formula_sum            'C16 H10 F9 N O3'
_chemical_formula_weight         435.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0070 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0130 0.0070 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0210 0.0120 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0330 0.0200 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.470(2)
_cell_length_b                   18.010(4)
_cell_length_c                   17.040(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.15(3)
_cell_angle_gamma                90
_cell_volume                     3344.9(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    500
_cell_measurement_theta_min      3.5
_cell_measurement_theta_max      35.0

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.729
_exptl_crystal_F_000             1744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.417
_shelx_estimated_absorpt_T_min   0.935
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_process_details   'Scala (Evans, 2005)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.96990
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  'MAR CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48650
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.533
_diffrn_reflns_theta_max         38.459
_diffrn_reflns_theta_full        35.587
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             7081
_reflns_number_gt                5513
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       Automar
_computing_cell_refinement       iMosflm
_computing_data_reduction        iMosflm
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0681P)²+1.36P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0031(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7081
_refine_ls_number_parameters     524
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1288
_refine_ls_wR_factor_gt          0.1187
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.60945(10) 0.35139(6) 0.66378(7) 0.0336(3) Uani 1 1 d . . . . .
F2 F 0.60301(13) 0.23316(7) 0.67731(7) 0.0463(3) Uani 1 1 d . . . . .
F3 F 0.74653(10) 0.28326(9) 0.63865(8) 0.0540(4) Uani 1 1 d . . . . .
F4 F 0.05074(11) 0.35488(8) 0.57239(8) 0.0465(3) Uani 1 1 d . . . . .
F5 F 0.20319(11) 0.33062(8) 0.67918(8) 0.0471(3) Uani 1 1 d . . . . .
F6 F 0.09788(13) 0.42972(8) 0.67544(9) 0.0531(4) Uani 1 1 d . . . . .
F7 F 0.05714(11) 0.55695(8) 0.58195(10) 0.0532(4) Uani 1 1 d . . . . .
F8 F 0.22009(13) 0.57963(8) 0.68356(8) 0.0530(4) Uani 1 1 d . . . . .
F9 F 0.19852(13) 0.62537(7) 0.56240(10) 0.0536(4) Uani 1 1 d . . . . .
O1 O 0.40693(10) 0.43959(7) 0.55983(8) 0.0247(3) Uani 1 1 d . . . . .
O2 O 0.40393(11) 0.41108(7) 0.40269(8) 0.0270(3) Uani 1 1 d . . . . .
O3 O 0.60919(12) 0.26172(10) 0.49046(9) 0.0426(4) Uani 1 1 d . . . . .
C1 C 0.35796(16) 0.28251(11) 0.42649(11) 0.0251(4) Uani 1 1 d . . . . .
H1A H 0.2903 0.2462 0.4175 0.030 Uiso 1 1 calc R U . . .
H1B H 0.4122 0.2660 0.3946 0.030 Uiso 1 1 calc R U . . .
N2 N 0.42848(13) 0.28605(9) 0.51548(9) 0.0229(3) Uani 1 1 d . . . . .
C3 C 0.35717(15) 0.30827(10) 0.56996(11) 0.0233(4) Uani 1 1 d . . . . .
H3A H 0.4099 0.3071 0.6283 0.028 Uiso 1 1 calc R U . . .
H3B H 0.2880 0.2735 0.5636 0.028 Uiso 1 1 calc R U . . .
C3A C 0.30847(15) 0.38661(10) 0.54655(11) 0.0226(4) Uani 1 1 d . . . . .
C4 C 0.22829(15) 0.42608(11) 0.59183(11) 0.0251(4) Uani 1 1 d . . . . .
C5 C 0.24184(16) 0.49843(11) 0.57998(12) 0.0276(4) Uani 1 1 d . . . . .
C6 C 0.33119(16) 0.50338(11) 0.52857(12) 0.0270(4) Uani 1 1 d . . . . .
H6 H 0.3762 0.5515 0.5328 0.032 Uiso 1 1 calc R U . . .
C6A C 0.25445(16) 0.47971(11) 0.43889(11) 0.0261(4) Uani 1 1 d . . . . .
H6A H 0.1748 0.5070 0.4177 0.031 Uiso 1 1 calc R U . . .
C7 C 0.32591(16) 0.47511(11) 0.37406(12) 0.0295(4) Uani 1 1 d . . . . .
H7 H 0.3693 0.5216 0.3670 0.035 Uiso 1 1 calc R U . . .
C8 C 0.23405(17) 0.44427(13) 0.29491(12) 0.0336(5) Uani 1 1 d . . . . .
H8 H 0.1934 0.4712 0.2461 0.040 Uiso 1 1 calc R U . . .
C9 C 0.22266(16) 0.37223(12) 0.30838(11) 0.0291(4) Uani 1 1 d . . . . .
H9 H 0.1736 0.3368 0.2712 0.035 Uiso 1 1 calc R U . . .
C9A C 0.30601(15) 0.35885(11) 0.39696(11) 0.0234(4) Uani 1 1 d . . . . .
C9B C 0.23752(15) 0.39565(10) 0.45312(10) 0.0225(4) Uani 1 1 d . . . . .
H9B H 0.1495 0.3805 0.4385 0.027 Uiso 1 1 calc R U . . .
C10 C 0.55153(16) 0.27798(11) 0.53738(11) 0.0281(4) Uani 1 1 d . . . . .
C11 C 0.62707(16) 0.28677(11) 0.63014(12) 0.0291(4) Uani 1 1 d . . . . .
C12 C 0.14518(17) 0.38628(12) 0.62999(11) 0.0290(4) Uani 1 1 d . . . . .
C13 C 0.17948(18) 0.56471(12) 0.60230(13) 0.0354(5) Uani 1 1 d . . . . .
F10 F 0.92708(10) 0.36441(7) 0.78805(6) 0.0330(3) Uani 1 1 d . . . . .
F11 F 0.92037(13) 0.24405(7) 0.78923(8) 0.0489(3) Uani 1 1 d . . . . .
F12 F 1.09381(11) 0.30088(9) 0.81727(8) 0.0527(4) Uani 1 1 d . . . . .
F13 F 0.49757(10) 0.32934(7) 0.80038(7) 0.0369(3) Uani 1 1 d . . . . .
F14 F 0.43612(11) 0.38491(7) 0.89193(8) 0.0406(3) Uani 1 1 d . . . . .
F15 F 0.40570(11) 0.43517(8) 0.77226(9) 0.0531(4) Uani 1 1 d . . . . .
F16 F 0.50618(14) 0.59246(9) 0.77529(8) 0.0564(4) Uani 1 1 d . . . . .
F17 F 0.43915(13) 0.56120(8) 0.87352(10) 0.0578(4) Uani 1 1 d . . . . .
F18 F 0.59494(14) 0.63240(8) 0.89820(12) 0.0748(6) Uani 1 1 d . . . . .
O4 O 0.81468(10) 0.45395(7) 0.89174(7) 0.0215(3) Uani 1 1 d . . . . .
O5 O 0.96245(10) 0.43201(7) 1.04903(7) 0.0227(3) Uani 1 1 d . . . . .
O6 O 1.10073(12) 0.29456(9) 0.96943(8) 0.0349(3) Uani 1 1 d . . . . .
C14 C 0.90405(16) 0.30182(11) 1.03143(11) 0.0253(4) Uani 1 1 d . . . . .
H14A H 0.9887 0.2876 1.0640 0.030 Uiso 1 1 calc R U . . .
H14B H 0.8469 0.2644 1.0413 0.030 Uiso 1 1 calc R U . . .
N15 N 0.89251(13) 0.30403(9) 0.94223(9) 0.0235(3) Uani 1 1 d . . . . .
C16 C 0.76736(15) 0.32165(11) 0.88696(11) 0.0246(4) Uani 1 1 d . . . . .
H16A H 0.7078 0.2849 0.8949 0.030 Uiso 1 1 calc R U . . .
H16B H 0.7657 0.3198 0.8286 0.030 Uiso 1 1 calc R U . . .
C16A C 0.73335(15) 0.39908(10) 0.90800(10) 0.0215(4) Uani 1 1 d . . . . .
C17 C 0.60798(15) 0.43575(11) 0.86327(10) 0.0237(4) Uani 1 1 d . . . . .
C18 C 0.62842(15) 0.50897(11) 0.87313(11) 0.0252(4) Uani 1 1 d . . . . .
C19 C 0.76526(15) 0.51765(10) 0.92178(11) 0.0236(4) Uani 1 1 d . . . . .
H19 H 0.8027 0.5665 0.9154 0.028 Uiso 1 1 calc R U . . .
C19A C 0.77522(15) 0.49542(10) 1.01243(10) 0.0234(4) Uani 1 1 d . . . . .
H19A H 0.7143 0.5219 1.0335 0.028 Uiso 1 1 calc R U . . .
C20 C 0.90721(16) 0.49560(11) 1.07557(10) 0.0250(4) Uani 1 1 d . . . . .
H20 H 0.9533 0.5433 1.0799 0.030 Uiso 1 1 calc R U . . .
C21 C 0.89360(17) 0.46624(12) 1.15666(11) 0.0303(4) Uani 1 1 d . . . . .
H21 H 0.8980 0.4943 1.2047 0.036 Uiso 1 1 calc R U . . .
C22 C 0.87420(16) 0.39314(12) 1.14624(11) 0.0285(4) Uani 1 1 d . . . . .
H22 H 0.8629 0.3584 1.1852 0.034 Uiso 1 1 calc R U . . .
C22A C 0.87424(15) 0.37775(10) 1.05809(10) 0.0225(4) Uani 1 1 d . . . . .
C22B C 0.75031(15) 0.41070(10) 1.00160(10) 0.0214(4) Uani 1 1 d . . . . .
H22B H 0.6777 0.3944 1.0178 0.026 Uiso 1 1 calc R U . . .
C23 C 0.99629(16) 0.30190(11) 0.92121(11) 0.0265(4) Uani 1 1 d . . . . .
C24 C 0.98348(17) 0.30345(12) 0.82775(12) 0.0314(4) Uani 1 1 d . . . . .
C25 C 0.48696(16) 0.39680(11) 0.83171(11) 0.0276(4) Uani 1 1 d . . . . .
C26 C 0.54126(17) 0.57352(12) 0.85432(12) 0.0319(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C11 1.340(2) . ?
F2 C11 1.339(2) . ?
F3 C11 1.334(2) . ?
F4 C12 1.339(2) . ?
F5 C12 1.343(2) . ?
F6 C12 1.330(2) . ?
F7 C13 1.344(2) . ?
F8 C13 1.343(3) . ?
F9 C13 1.340(3) . ?
O1 C6 1.439(2) . ?
O1 C3A 1.441(2) . ?
O2 C9A 1.445(2) . ?
O2 C7 1.448(2) . ?
O3 C10 1.222(2) . ?
C1 N2 1.481(2) . ?
C1 C9A 1.520(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
N2 C10 1.351(2) . ?
N2 C3 1.471(2) . ?
C3 C3A 1.524(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3A C4 1.546(2) . ?
C3A C9B 1.554(2) . ?
C4 C5 1.335(3) . ?
C4 C12 1.494(3) . ?
C5 C13 1.500(3) . ?
C5 C6 1.544(3) . ?
C6 C6A 1.567(3) . ?
C6 H6 1.0000 . ?
C6A C9B 1.555(3) . ?
C6A C7 1.569(3) . ?
C6A H6A 1.0000 . ?
C7 C8 1.534(3) . ?
C7 H7 1.0000 . ?
C8 C9 1.331(3) . ?
C8 H8 0.9500 . ?
C9 C9A 1.533(2) . ?
C9 H9 0.9500 . ?
C9A C9B 1.562(2) . ?
C9B H9B 1.0000 . ?
C10 C11 1.556(3) . ?
F10 C24 1.345(2) . ?
F11 C24 1.343(3) . ?
F12 C24 1.333(2) . ?
F13 C25 1.348(2) . ?
F14 C25 1.346(2) . ?
F15 C25 1.336(2) . ?
F16 C26 1.324(2) . ?
F17 C26 1.329(2) . ?
F18 C26 1.333(3) . ?
O4 C19 1.442(2) . ?
O4 C16A 1.444(2) . ?
O5 C20 1.448(2) . ?
O5 C22A 1.449(2) . ?
O6 C23 1.231(2) . ?
C14 N15 1.485(2) . ?
C14 C22A 1.513(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
N15 C23 1.346(2) . ?
N15 C16 1.485(2) . ?
C16 C16A 1.521(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16A C17 1.550(2) . ?
C16A C22B 1.560(2) . ?
C17 C18 1.341(3) . ?
C17 C25 1.498(2) . ?
C18 C26 1.501(3) . ?
C18 C19 1.538(2) . ?
C19 C19A 1.565(2) . ?
C19 H19 1.0000 . ?
C19A C22B 1.553(3) . ?
C19A C20 1.560(2) . ?
C19A H19A 1.0000 . ?
C20 C21 1.532(3) . ?
C20 H20 1.0000 . ?
C21 C22 1.338(3) . ?
C21 H21 0.9500 . ?
C22 C22A 1.528(2) . ?
C22 H22 0.9500 . ?
C22A C22B 1.564(2) . ?
C22B H22B 1.0000 . ?
C23 C24 1.553(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O1 C3A 96.74(12) . . ?
C9A O2 C7 96.31(13) . . ?
N2 C1 C9A 109.43(15) . . ?
N2 C1 H1A 109.8 . . ?
C9A C1 H1A 109.8 . . ?
N2 C1 H1B 109.8 . . ?
C9A C1 H1B 109.8 . . ?
H1A C1 H1B 108.2 . . ?
C10 N2 C3 126.40(15) . . ?
C10 N2 C1 117.95(15) . . ?
C3 N2 C1 115.09(13) . . ?
N2 C3 C3A 108.50(14) . . ?
N2 C3 H3A 110.0 . . ?
C3A C3 H3A 110.0 . . ?
N2 C3 H3B 110.0 . . ?
C3A C3 H3B 110.0 . . ?
H3A C3 H3B 108.4 . . ?
O1 C3A C3 111.49(13) . . ?
O1 C3A C4 100.14(14) . . ?
C3 C3A C4 121.45(15) . . ?
O1 C3A C9B 103.06(13) . . ?
C3 C3A C9B 113.41(15) . . ?
C4 C3A C9B 105.07(13) . . ?
C5 C4 C12 130.87(17) . . ?
C5 C4 C3A 104.96(15) . . ?
C12 C4 C3A 123.79(17) . . ?
C4 C5 C13 130.62(18) . . ?
C4 C5 C6 105.74(16) . . ?
C13 C5 C6 123.43(17) . . ?
O1 C6 C5 100.06(14) . . ?
O1 C6 C6A 103.58(14) . . ?
C5 C6 C6A 105.49(14) . . ?
O1 C6 H6 115.3 . . ?
C5 C6 H6 115.3 . . ?
C6A C6 H6 115.3 . . ?
C9B C6A C6 99.93(14) . . ?
C9B C6A C7 100.15(14) . . ?
C6 C6A C7 116.30(14) . . ?
C9B C6A H6A 113.0 . . ?
C6 C6A H6A 113.0 . . ?
C7 C6A H6A 113.0 . . ?
O2 C7 C8 101.01(16) . . ?
O2 C7 C6A 102.03(14) . . ?
C8 C7 C6A 105.77(14) . . ?
O2 C7 H7 115.4 . . ?
C8 C7 H7 115.4 . . ?
C6A C7 H7 115.4 . . ?
C9 C8 C7 106.18(17) . . ?
C9 C8 H8 126.9 . . ?
C7 C8 H8 126.9 . . ?
C8 C9 C9A 104.97(17) . . ?
C8 C9 H9 127.5 . . ?
C9A C9 H9 127.5 . . ?
O2 C9A C1 110.49(14) . . ?
O2 C9A C9 101.39(14) . . ?
C1 C9A C9 121.85(16) . . ?
O2 C9A C9B 102.18(14) . . ?
C1 C9A C9B 113.64(14) . . ?
C9 C9A C9B 104.95(14) . . ?
C3A C9B C6A 102.17(14) . . ?
C3A C9B C9A 112.35(14) . . ?
C6A C9B C9A 101.92(14) . . ?
C3A C9B H9B 113.1 . . ?
C6A C9B H9B 113.1 . . ?
C9A C9B H9B 113.1 . . ?
O3 C10 N2 125.25(17) . . ?
O3 C10 C11 116.47(16) . . ?
N2 C10 C11 118.23(16) . . ?
F3 C11 F2 107.31(16) . . ?
F3 C11 F1 106.34(16) . . ?
F2 C11 F1 106.43(15) . . ?
F3 C11 C10 109.49(15) . . ?
F2 C11 C10 112.51(16) . . ?
F1 C11 C10 114.35(15) . . ?
F6 C12 F4 106.95(16) . . ?
F6 C12 F5 106.76(16) . . ?
F4 C12 F5 105.83(17) . . ?
F6 C12 C4 113.74(17) . . ?
F4 C12 C4 111.33(15) . . ?
F5 C12 C4 111.76(15) . . ?
F9 C13 F8 107.51(17) . . ?
F9 C13 F7 106.02(17) . . ?
F8 C13 F7 106.60(17) . . ?
F9 C13 C5 110.74(17) . . ?
F8 C13 C5 112.39(17) . . ?
F7 C13 C5 113.20(17) . . ?
C19 O4 C16A 97.32(12) . . ?
C20 O5 C22A 96.43(12) . . ?
N15 C14 C22A 109.07(14) . . ?
N15 C14 H14A 109.9 . . ?
C22A C14 H14A 109.9 . . ?
N15 C14 H14B 109.9 . . ?
C22A C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?
C23 N15 C14 117.87(15) . . ?
C23 N15 C16 126.68(15) . . ?
C14 N15 C16 114.53(13) . . ?
N15 C16 C16A 108.34(14) . . ?
N15 C16 H16A 110.0 . . ?
C16A C16 H16A 110.0 . . ?
N15 C16 H16B 110.0 . . ?
C16A C16 H16B 110.0 . . ?
H16A C16 H16B 108.4 . . ?
O4 C16A C16 110.73(13) . . ?
O4 C16A C17 99.78(13) . . ?
C16 C16A C17 122.80(15) . . ?
O4 C16A C22B 102.84(13) . . ?
C16 C16A C22B 113.88(14) . . ?
C17 C16A C22B 104.29(13) . . ?
C18 C17 C25 127.73(16) . . ?
C18 C17 C16A 104.97(15) . . ?
C25 C17 C16A 126.24(17) . . ?
C17 C18 C26 131.00(17) . . ?
C17 C18 C19 106.07(15) . . ?
C26 C18 C19 122.43(17) . . ?
O4 C19 C18 100.12(14) . . ?
O4 C19 C19A 103.35(14) . . ?
C18 C19 C19A 104.74(14) . . ?
O4 C19 H19 115.6 . . ?
C18 C19 H19 115.6 . . ?
C19A C19 H19 115.6 . . ?
C22B C19A C20 100.78(14) . . ?
C22B C19A C19 100.37(13) . . ?
C20 C19A C19 115.91(14) . . ?
C22B C19A H19A 112.8 . . ?
C20 C19A H19A 112.8 . . ?
C19 C19A H19A 112.8 . . ?
O5 C20 C21 100.74(15) . . ?
O5 C20 C19A 102.00(13) . . ?
C21 C20 C19A 105.76(14) . . ?
O5 C20 H20 115.5 . . ?
C21 C20 H20 115.5 . . ?
C19A C20 H20 115.5 . . ?
C22 C21 C20 106.22(16) . . ?
C22 C21 H21 126.9 . . ?
C20 C21 H21 126.9 . . ?
C21 C22 C22A 104.96(16) . . ?
C21 C22 H22 127.5 . . ?
C22A C22 H22 127.5 . . ?
O5 C22A C14 110.29(13) . . ?
O5 C22A C22 101.33(14) . . ?
C14 C22A C22 121.90(15) . . ?
O5 C22A C22B 102.09(13) . . ?
C14 C22A C22B 113.90(14) . . ?
C22 C22A C22B 104.93(14) . . ?
C19A C22B C16A 102.31(13) . . ?
C19A C22B C22A 101.62(13) . . ?
C16A C22B C22A 112.23(13) . . ?
C19A C22B H22B 113.2 . . ?
C16A C22B H22B 113.2 . . ?
C22A C22B H22B 113.2 . . ?
O6 C23 N15 125.66(17) . . ?
O6 C23 C24 116.61(16) . . ?
N15 C23 C24 117.59(16) . . ?
F12 C24 F11 107.26(16) . . ?
F12 C24 F10 106.79(17) . . ?
F11 C24 F10 107.64(15) . . ?
F12 C24 C23 110.26(15) . . ?
F11 C24 C23 110.57(17) . . ?
F10 C24 C23 114.04(15) . . ?
F15 C25 F14 107.15(15) . . ?
F15 C25 F13 107.09(15) . . ?
F14 C25 F13 105.81(16) . . ?
F15 C25 C17 112.32(17) . . ?
F14 C25 C17 111.96(15) . . ?
F13 C25 C17 112.12(14) . . ?
F16 C26 F17 106.34(16) . . ?
F16 C26 F18 107.84(19) . . ?
F17 C26 F18 106.45(18) . . ?
F16 C26 C18 112.82(16) . . ?
F17 C26 C18 113.41(17) . . ?
F18 C26 C18 109.62(16) . . ?

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
C9A C1 N2 C10 -111.17(18) . . . . ?
C9A C1 N2 C3 60.86(19) . . . . ?
C10 N2 C3 C3A 109.1(2) . . . . ?
C1 N2 C3 C3A -62.13(19) . . . . ?
C6 O1 C3A C3 177.16(14) . . . . ?
C6 O1 C3A C4 -53.04(15) . . . . ?
C6 O1 C3A C9B 55.18(15) . . . . ?
N2 C3 C3A O1 -63.09(18) . . . . ?
N2 C3 C3A C4 179.36(14) . . . . ?
N2 C3 C3A C9B 52.71(18) . . . . ?
O1 C3A C4 C5 33.81(17) . . . . ?
C3 C3A C4 C5 156.88(16) . . . . ?
C9B C3A C4 C5 -72.80(17) . . . . ?
O1 C3A C4 C12 -152.61(16) . . . . ?
C3 C3A C4 C12 -29.5(2) . . . . ?
C9B C3A C4 C12 100.77(19) . . . . ?
C12 C4 C5 C13 1.2(3) . . . . ?
C3A C4 C5 C13 174.10(18) . . . . ?
C12 C4 C5 C6 -173.61(18) . . . . ?
C3A C4 C5 C6 -0.68(18) . . . . ?
C3A O1 C6 C5 52.48(15) . . . . ?
C3A O1 C6 C6A -56.31(15) . . . . ?
C4 C5 C6 O1 -32.70(17) . . . . ?
C13 C5 C6 O1 152.04(17) . . . . ?
C4 C5 C6 C6A 74.55(18) . . . . ?
C13 C5 C6 C6A -100.7(2) . . . . ?
O1 C6 C6A C9B 34.89(16) . . . . ?
C5 C6 C6A C9B -69.79(16) . . . . ?
O1 C6 C6A C7 -71.73(19) . . . . ?
C5 C6 C6A C7 -176.42(16) . . . . ?
C9A O2 C7 C8 -50.33(15) . . . . ?
C9A O2 C7 C6A 58.60(15) . . . . ?
C9B C6A C7 O2 -36.83(16) . . . . ?
C6 C6A C7 O2 69.66(19) . . . . ?
C9B C6A C7 C8 68.43(17) . . . . ?
C6 C6A C7 C8 174.92(16) . . . . ?
O2 C7 C8 C9 31.47(18) . . . . ?
C6A C7 C8 C9 -74.53(19) . . . . ?
C7 C8 C9 C9A 1.09(19) . . . . ?
C7 O2 C9A C1 -178.13(14) . . . . ?
C7 O2 C9A C9 51.33(15) . . . . ?
C7 O2 C9A C9B -56.89(15) . . . . ?
N2 C1 C9A O2 64.61(17) . . . . ?
N2 C1 C9A C9 -176.69(14) . . . . ?
N2 C1 C9A C9B -49.57(18) . . . . ?
C8 C9 C9A O2 -33.48(18) . . . . ?
C8 C9 C9A C1 -156.54(16) . . . . ?
C8 C9 C9A C9B 72.58(17) . . . . ?
O1 C3A C9B C6A -33.13(16) . . . . ?
C3 C3A C9B C6A -153.81(13) . . . . ?
C4 C3A C9B C6A 71.32(16) . . . . ?
O1 C3A C9B C9A 75.36(17) . . . . ?
C3 C3A C9B C9A -45.33(19) . . . . ?
C4 C3A C9B C9A 179.81(14) . . . . ?
C6 C6A C9B C3A -0.90(15) . . . . ?
C7 C6A C9B C3A 118.33(14) . . . . ?
C6 C6A C9B C9A -117.20(14) . . . . ?
C7 C6A C9B C9A 2.03(15) . . . . ?
O2 C9A C9B C3A -75.32(17) . . . . ?
C1 C9A C9B C3A 43.7(2) . . . . ?
C9 C9A C9B C3A 179.21(14) . . . . ?
O2 C9A C9B C6A 33.33(15) . . . . ?
C1 C9A C9B C6A 152.37(14) . . . . ?
C9 C9A C9B C6A -72.14(16) . . . . ?
C3 N2 C10 O3 -177.6(2) . . . . ?
C1 N2 C10 O3 -6.5(3) . . . . ?
C3 N2 C10 C11 5.1(3) . . . . ?
C1 N2 C10 C11 176.08(16) . . . . ?
O3 C10 C11 F3 7.6(3) . . . . ?
N2 C10 C11 F3 -174.74(18) . . . . ?
O3 C10 C11 F2 -111.6(2) . . . . ?
N2 C10 C11 F2 66.0(2) . . . . ?
O3 C10 C11 F1 126.8(2) . . . . ?
N2 C10 C11 F1 -55.5(2) . . . . ?
C5 C4 C12 F6 -17.0(3) . . . . ?
C3A C4 C12 F6 171.18(16) . . . . ?
C5 C4 C12 F4 103.9(2) . . . . ?
C3A C4 C12 F4 -67.9(2) . . . . ?
C5 C4 C12 F5 -138.0(2) . . . . ?
C3A C4 C12 F5 50.2(2) . . . . ?
C4 C5 C13 F9 -165.39(19) . . . . ?
C6 C5 C13 F9 8.6(3) . . . . ?
C4 C5 C13 F8 74.4(3) . . . . ?
C6 C5 C13 F8 -111.7(2) . . . . ?
C4 C5 C13 F7 -46.5(3) . . . . ?
C6 C5 C13 F7 127.48(19) . . . . ?
C22A C14 N15 C23 107.70(18) . . . . ?
C22A C14 N15 C16 -62.09(19) . . . . ?
C23 N15 C16 C16A -106.3(2) . . . . ?
C14 N15 C16 C16A 62.41(19) . . . . ?
C19 O4 C16A C16 -176.60(13) . . . . ?
C19 O4 C16A C17 52.64(14) . . . . ?
C19 O4 C16A C22B -54.59(14) . . . . ?
N15 C16 C16A O4 63.36(17) . . . . ?
N15 C16 C16A C17 -179.26(14) . . . . ?
N15 C16 C16A C22B -51.93(18) . . . . ?
O4 C16A C17 C18 -33.79(16) . . . . ?
C16 C16A C17 C18 -156.36(16) . . . . ?
C22B C16A C17 C18 72.26(17) . . . . ?
O4 C16A C17 C25 157.29(16) . . . . ?
C16 C16A C17 C25 34.7(2) . . . . ?
C22B C16A C17 C25 -96.66(19) . . . . ?
C25 C17 C18 C26 -2.0(3) . . . . ?
C16A C17 C18 C26 -170.75(18) . . . . ?
C25 C17 C18 C19 169.83(16) . . . . ?
C16A C17 C18 C19 1.13(18) . . . . ?
C16A O4 C19 C18 -52.04(14) . . . . ?
C16A O4 C19 C19A 55.90(14) . . . . ?
C17 C18 C19 O4 31.93(17) . . . . ?
C26 C18 C19 O4 -155.33(15) . . . . ?
C17 C18 C19 C19A -74.89(17) . . . . ?
C26 C18 C19 C19A 97.85(19) . . . . ?
O4 C19 C19A C22B -34.67(15) . . . . ?
C18 C19 C19A C22B 69.77(16) . . . . ?
O4 C19 C19A C20 72.81(18) . . . . ?
C18 C19 C19A C20 177.24(15) . . . . ?
C22A O5 C20 C21 50.55(14) . . . . ?
C22A O5 C20 C19A -58.29(14) . . . . ?
C22B C19A C20 O5 36.64(15) . . . . ?
C19 C19A C20 O5 -70.59(18) . . . . ?
C22B C19A C20 C21 -68.31(16) . . . . ?
C19 C19A C20 C21 -175.54(16) . . . . ?
O5 C20 C21 C22 -31.88(18) . . . . ?
C19A C20 C21 C22 73.99(18) . . . . ?
C20 C21 C22 C22A -0.72(19) . . . . ?
C20 O5 C22A C14 178.09(13) . . . . ?
C20 O5 C22A C22 -51.47(15) . . . . ?
C20 O5 C22A C22B 56.69(14) . . . . ?
N15 C14 C22A O5 -63.33(17) . . . . ?
N15 C14 C22A C22 178.19(14) . . . . ?
N15 C14 C22A C22B 50.76(18) . . . . ?
C21 C22 C22A O5 33.17(17) . . . . ?
C21 C22 C22A C14 155.94(16) . . . . ?
C21 C22 C22A C22B -72.77(17) . . . . ?
C20 C19A C22B C16A -118.01(13) . . . . ?
C19 C19A C22B C16A 1.13(15) . . . . ?
C20 C19A C22B C22A -1.90(15) . . . . ?
C19 C19A C22B C22A 117.25(13) . . . . ?
O4 C16A C22B C19A 32.53(15) . . . . ?
C16 C16A C22B C19A 152.39(14) . . . . ?
C17 C16A C22B C19A -71.22(15) . . . . ?
O4 C16A C22B C22A -75.64(17) . . . . ?
C16 C16A C22B C22A 44.22(19) . . . . ?
C17 C16A C22B C22A -179.40(14) . . . . ?
O5 C22A C22B C19A -33.25(15) . . . . ?
C14 C22A C22B C19A -152.13(14) . . . . ?
C22 C22A C22B C19A 72.11(16) . . . . ?
O5 C22A C22B C16A 75.35(17) . . . . ?
C14 C22A C22B C16A -43.52(19) . . . . ?
C22 C22A C22B C16A -179.28(15) . . . . ?
C14 N15 C23 O6 3.8(3) . . . . ?
C16 N15 C23 O6 172.23(19) . . . . ?
C14 N15 C23 C24 179.41(16) . . . . ?
C16 N15 C23 C24 -12.2(3) . . . . ?
O6 C23 C24 F12 -3.9(3) . . . . ?
N15 C23 C24 F12 -179.87(17) . . . . ?
O6 C23 C24 F11 114.55(19) . . . . ?
N15 C23 C24 F11 -61.4(2) . . . . ?
O6 C23 C24 F10 -124.01(19) . . . . ?
N15 C23 C24 F10 60.0(2) . . . . ?
C18 C17 C25 F15 35.9(3) . . . . ?
C16A C17 C25 F15 -157.69(16) . . . . ?
C18 C17 C25 F14 -84.7(2) . . . . ?
C16A C17 C25 F14 81.7(2) . . . . ?
C18 C17 C25 F13 156.54(17) . . . . ?
C16A C17 C25 F13 -37.0(2) . . . . ?
C17 C18 C26 F16 -80.5(3) . . . . ?
C19 C18 C26 F16 108.7(2) . . . . ?
C17 C18 C26 F17 40.5(3) . . . . ?
C19 C18 C26 F17 -130.29(19) . . . . ?
C17 C18 C26 F18 159.3(2) . . . . ?
C19 C18 C26 F18 -11.5(3) . . . . ?

_refine_diff_density_max         0.422
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.061

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1570124'
_audit_update_record             
;
2017-08-22 deposited with the CCDC.
2018-01-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H17 F6 N O2'
_chemical_formula_sum            'C21 H17 F6 N O2'
_chemical_formula_weight         429.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0070 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0130 0.0070 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0210 0.0120 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0330 0.0200 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

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

_cell_length_a                   18.903(4)
_cell_length_b                   5.5733(11)
_cell_length_c                   36.080(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3801.1(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    600
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      33.0

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_F_000             1760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.300
_shelx_estimated_absorpt_T_min   0.937
_shelx_estimated_absorpt_T_max   0.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_process_details   'Scala (Evans, 2005)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.96990
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  'MAR CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32286
_diffrn_reflns_av_unetI/netI     0.1216
_diffrn_reflns_av_R_equivalents  0.1078
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         3.321
_diffrn_reflns_theta_max         36.000
_diffrn_reflns_theta_full        35.587
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measured_fraction_theta_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_point_group_measured_fraction_full 0.944
_reflns_number_total             6705
_reflns_number_gt                4745
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.938
_reflns_Friedel_fraction_max     0.930
_reflns_Friedel_fraction_full    0.930

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

_computing_data_collection       'Marccd (Doyle, 2011)'
_computing_cell_refinement       'iMosflm (Battye et al., 2011)'
_computing_data_reduction        iMosflm
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  SHELXTL
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+20P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1846 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6705
_refine_ls_number_parameters     529
_refine_ls_number_restraints     45
_refine_ls_R_factor_all          0.1426
_refine_ls_R_factor_gt           0.1099
_refine_ls_wR_factor_ref         0.2601
_refine_ls_wR_factor_gt          0.2352
_refine_ls_goodness_of_fit_ref   0.915
_refine_ls_restrained_S_all      0.915
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.2313(3) 0.5655(14) 0.38288(15) 0.072(2) Uani 1 1 d D . . . .
F2 F 0.2341(3) 0.6304(15) 0.44230(13) 0.082(3) Uani 1 1 d D . . . .
F3 F 0.2863(3) 0.8780(10) 0.4045(2) 0.084(3) Uani 1 1 d D . . . .
F4 F 0.3304(6) 0.6040(18) 0.4959(3) 0.116(3) Uani 0.75 1 d D . P A 1
F5 F 0.2973(5) 0.234(2) 0.4863(3) 0.116(3) Uani 0.75 1 d D . P A 1
F6 F 0.4053(4) 0.312(2) 0.5043(3) 0.116(3) Uani 0.75 1 d D . P A 1
F4' F 0.3849(14) 0.558(4) 0.5031(7) 0.116(3) Uani 0.25 1 d D . P A 2
F5' F 0.2836(6) 0.381(6) 0.4942(8) 0.116(3) Uani 0.25 1 d D . P A 2
F6' F 0.3816(15) 0.175(3) 0.4911(8) 0.116(3) Uani 0.25 1 d D . P A 2
O1 O 0.4284(3) 0.2649(11) 0.3903(2) 0.0394(16) Uani 1 1 d . . . . .
O2 O 0.5531(4) 0.4768(11) 0.3701(2) 0.0337(16) Uani 1 1 d . . . . .
C1 C 0.4828(7) 0.692(3) 0.3237(4) 0.068(4) Uani 1 1 d . . . . .
H1A H 0.4565 0.8425 0.3190 0.081 Uiso 1 1 calc R U . . .
H1B H 0.5229 0.6848 0.3061 0.081 Uiso 1 1 calc R U . . .
N2 N 0.4372(6) 0.493(3) 0.3173(3) 0.074(4) Uani 1 1 d D . . . .
C3 C 0.3727(6) 0.501(3) 0.3417(3) 0.057(3) Uani 1 1 d . . . . .
H3A H 0.3414 0.3635 0.3361 0.068 Uiso 1 1 calc R U . . .
H3B H 0.3460 0.6510 0.3372 0.068 Uiso 1 1 calc R U . . .
C3A C 0.3963(5) 0.4906(16) 0.3816(3) 0.033(2) Uani 1 1 d . . . . .
C4 C 0.3418(5) 0.5008(16) 0.4132(3) 0.033(2) Uani 1 1 d . . . . .
C5 C 0.3721(6) 0.398(2) 0.4419(3) 0.046(2) Uani 1 1 d . . . . .
C6 C 0.4443(5) 0.326(2) 0.4281(3) 0.044(2) Uani 1 1 d . . . . .
H6 H 0.4668 0.1928 0.4425 0.053 Uiso 1 1 calc R U . . .
C6A C 0.4891(6) 0.554(2) 0.4256(3) 0.051(3) Uani 1 1 d . . . . .
H6A H 0.4881 0.6512 0.4489 0.061 Uiso 1 1 calc R U . . .
C7 C 0.5670(6) 0.526(2) 0.4087(4) 0.048(3) Uani 1 1 d . . . . .
H7 H 0.5986 0.4086 0.4217 0.058 Uiso 1 1 calc R U . . .
C8 C 0.5958(6) 0.780(2) 0.4047(4) 0.059(3) Uani 1 1 d . . . . .
H8 H 0.6312 0.8527 0.4196 0.071 Uiso 1 1 calc R U . . .
C9 C 0.5616(6) 0.8792(19) 0.3764(4) 0.054(3) Uani 1 1 d . . . . .
H9 H 0.5681 1.0368 0.3670 0.065 Uiso 1 1 calc R U . . .
C9A C 0.5108(5) 0.6947(17) 0.3624(3) 0.044(2) Uani 1 1 d . . . . .
C9B C 0.4506(5) 0.6855(17) 0.3914(3) 0.031(2) Uani 1 1 d . . . . .
H9B H 0.4295 0.8452 0.3975 0.037 Uiso 1 1 calc R U . . .
C10 C 0.4148(10) 0.485(5) 0.2783(6) 0.127(9) Uani 1 1 d . . . . .
H10A H 0.4007 0.6481 0.2703 0.152 Uiso 1 1 calc R U . . .
H10B H 0.3728 0.3797 0.2761 0.152 Uiso 1 1 calc R U . . .
C11 C 0.4706(8) 0.396(4) 0.2533(3) 0.091(5) Uani 1 1 d D . . . .
C12 C 0.5169(8) 0.202(3) 0.2568(5) 0.096(6) Uani 1 1 d . . . . .
H12 H 0.5177 0.1191 0.2798 0.115 Uiso 1 1 calc R U . . .
C13 C 0.5601(9) 0.125(3) 0.2302(6) 0.086(5) Uani 1 1 d . . . . .
H13 H 0.5936 0.0029 0.2355 0.103 Uiso 1 1 calc R U . . .
C14 C 0.5572(8) 0.213(4) 0.1975(5) 0.091(6) Uani 1 1 d . . . . .
H14 H 0.5820 0.1386 0.1777 0.109 Uiso 1 1 calc R U . . .
C15 C 0.5194(10) 0.408(5) 0.1916(5) 0.121(9) Uani 1 1 d . . . . .
H15 H 0.5215 0.4845 0.1681 0.145 Uiso 1 1 calc R U . . .
C16 C 0.4754(13) 0.507(5) 0.2200(9) 0.148(11) Uani 1 1 d . . . . .
H16 H 0.4495 0.6504 0.2155 0.178 Uiso 1 1 calc R U . . .
C17 C 0.2724(3) 0.6444(12) 0.41088(16) 0.065(3) Uani 1 1 d D . . . .
C18 C 0.3516(4) 0.3886(18) 0.4831(2) 0.065(3) Uani 1 1 d D . . . .
F7 F 0.5480(3) 0.3992(10) 0.5959(2) 0.078(2) Uani 1 1 d D . . . .
F8 F 0.4940(4) 0.1717(15) 0.55587(14) 0.088(3) Uani 1 1 d D . . . .
F9 F 0.4913(3) 0.0809(13) 0.61446(15) 0.074(2) Uani 1 1 d D . . . .
F10 F 0.6014(5) 0.0927(16) 0.4977(3) 0.098(2) Uani 0.75 1 d D . P B 1
F11 F 0.6402(4) -0.2759(18) 0.4957(3) 0.098(2) Uani 0.75 1 d D . P B 1
F12 F 0.5326(4) -0.202(2) 0.5139(3) 0.098(2) Uani 0.75 1 d D . P B 1
F10' F 0.5712(13) 0.047(4) 0.4928(7) 0.098(2) Uani 0.25 1 d D . P B 2
F11' F 0.6610(8) -0.194(5) 0.4993(8) 0.098(2) Uani 0.25 1 d D . P B 2
F12' F 0.5556(12) -0.310(4) 0.5161(8) 0.098(2) Uani 0.25 1 d D . P B 2
O3 O 0.6873(4) -0.2214(13) 0.6052(2) 0.0414(17) Uani 1 1 d . . . . .
O4 O 0.8119(4) -0.0294(12) 0.6228(2) 0.0395(17) Uani 1 1 d . . . . .
C19 C 0.7489(7) 0.197(2) 0.6710(4) 0.062(4) Uani 1 1 d . . . . .
H19A H 0.7267 0.3561 0.6751 0.075 Uiso 1 1 calc R U . . .
H19B H 0.7892 0.1827 0.6884 0.075 Uiso 1 1 calc R U . . .
N20 N 0.6940(6) -0.001(3) 0.6798(2) 0.076(4) Uani 1 1 d D . . . .
C21 C 0.6329(6) 0.021(3) 0.6541(4) 0.053(3) Uani 1 1 d . . . . .
H21A H 0.6093 0.1770 0.6584 0.064 Uiso 1 1 calc R U . . .
H21B H 0.5983 -0.1076 0.6597 0.064 Uiso 1 1 calc R U . . .
C21A C 0.6543(5) 0.0037(18) 0.6142(3) 0.038(2) Uani 1 1 d . . . . .
C22 C 0.5988(5) 0.0232(19) 0.5831(3) 0.039(2) Uani 1 1 d . . . . .
C23 C 0.6275(6) -0.081(2) 0.5536(3) 0.051(3) Uani 1 1 d . . . . .
C24 C 0.7029(6) -0.173(2) 0.5675(3) 0.054(3) Uani 1 1 d . . . . .
H24 H 0.7235 -0.3094 0.5532 0.065 Uiso 1 1 calc R U . . .
C24A C 0.7488(5) 0.052(2) 0.5695(3) 0.040(2) Uani 1 1 d . . . . .
H24A H 0.7477 0.1492 0.5462 0.048 Uiso 1 1 calc R U . . .
C25 C 0.8251(5) 0.0179(19) 0.5852(3) 0.038(2) Uani 1 1 d . . . . .
H25 H 0.8546 -0.1044 0.5721 0.046 Uiso 1 1 calc R U . . .
C26 C 0.8574(6) 0.274(2) 0.5871(5) 0.065(4) Uani 1 1 d . . . . .
H26 H 0.8907 0.3443 0.5707 0.078 Uiso 1 1 calc R U . . .
C27 C 0.8271(6) 0.375(2) 0.6176(5) 0.066(4) Uani 1 1 d . . . . .
H27 H 0.8357 0.5291 0.6277 0.079 Uiso 1 1 calc R U . . .
C27A C 0.7764(6) 0.1841(18) 0.6317(3) 0.045(3) Uani 1 1 d . . . . .
C27B C 0.7135(5) 0.1847(18) 0.6034(3) 0.036(2) Uani 1 1 d . . . . .
H27B H 0.6955 0.3488 0.5973 0.044 Uiso 1 1 calc R U . . .
C28 C 0.6748(10) 0.005(5) 0.7163(4) 0.133(11) Uani 1 1 d . . . . .
H28A H 0.6322 -0.0964 0.7197 0.160 Uiso 1 1 calc R U . . .
H28B H 0.6618 0.1713 0.7229 0.160 Uiso 1 1 calc R U . . .
C29 C 0.7328(7) -0.083(3) 0.7435(2) 0.088(5) Uani 1 1 d D . . . .
C30 C 0.7749(8) -0.280(3) 0.7350(4) 0.093(6) Uani 1 1 d D . . . .
H30 H 0.7734 -0.3462 0.7108 0.111 Uiso 1 1 calc R U . . .
C31 C 0.8191(9) -0.380(3) 0.7615(4) 0.097(6) Uani 1 1 d D . . . .
H31 H 0.8483 -0.5127 0.7552 0.117 Uiso 1 1 calc R U . . .
C32 C 0.8209(7) -0.288(3) 0.7972(3) 0.083(5) Uani 1 1 d D . . . .
H32 H 0.8499 -0.3625 0.8154 0.099 Uiso 1 1 calc R U . . .
C33 C 0.7811(8) -0.089(3) 0.8069(4) 0.101(6) Uani 1 1 d D . . . .
H33 H 0.7842 -0.0181 0.8308 0.121 Uiso 1 1 calc R U . . .
C34 C 0.7365(8) 0.002(3) 0.7797(3) 0.089(6) Uani 1 1 d D . . . .
H34 H 0.7063 0.1318 0.7863 0.106 Uiso 1 1 calc R U . . .
C35 C 0.5327(3) 0.1701(12) 0.58727(15) 0.051(3) Uani 1 1 d D . . . .
C36 C 0.5999(4) -0.1214(17) 0.5149(2) 0.081(5) Uani 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C17 1.348(4) . ?
F2 C17 1.347(4) . ?
F3 C17 1.348(4) . ?
F4 C18 1.346(4) . ?
F5 C18 1.343(4) . ?
F6 C18 1.340(4) . ?
F4' C18 1.346(4) . ?
F5' C18 1.345(4) . ?
F6' C18 1.348(4) . ?
O1 C3A 1.431(11) . ?
O1 C6 1.436(13) . ?
O2 C7 1.445(14) . ?
O2 C9A 1.481(11) . ?
C1 N2 1.422(19) . ?
C1 C9A 1.493(17) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
N2 C10 1.47(2) . ?
N2 C3 1.505(15) . ?
C3 C3A 1.509(16) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3A C9B 1.535(13) . ?
C3A C4 1.538(13) . ?
C4 C5 1.316(15) . ?
C4 C17 1.539(11) . ?
C5 C6 1.508(15) . ?
C5 C18 1.539(13) . ?
C6 C6A 1.532(15) . ?
C6 H6 1.0000 . ?
C6A C7 1.601(16) . ?
C6A C9B 1.611(15) . ?
C6A H6A 1.0000 . ?
C7 C8 1.524(16) . ?
C7 H7 1.0000 . ?
C8 C9 1.329(19) . ?
C8 H8 0.9500 . ?
C9 C9A 1.495(15) . ?
C9 H9 0.9500 . ?
C9A C9B 1.546(14) . ?
C9B H9B 1.0000 . ?
C10 C11 1.47(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C16 1.36(3) . ?
C11 C12 1.40(2) . ?
C12 C13 1.33(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.28(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.32(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.43(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
F7 C35 1.346(4) . ?
F8 C35 1.348(4) . ?
F9 C35 1.349(4) . ?
F10 C36 1.346(4) . ?
F11 C36 1.342(4) . ?
F12 C36 1.350(4) . ?
F10' C36 1.346(4) . ?
F11' C36 1.348(4) . ?
F12' C36 1.346(4) . ?
O3 C24 1.417(14) . ?
O3 C21A 1.439(12) . ?
O4 C27A 1.403(12) . ?
O4 C25 1.404(14) . ?
C19 C27A 1.515(18) . ?
C19 N20 1.551(19) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
N20 C28 1.366(19) . ?
N20 C21 1.486(13) . ?
C21 C21A 1.500(16) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21A C22 1.541(14) . ?
C21A C27B 1.556(15) . ?
C22 C23 1.328(16) . ?
C22 C35 1.501(12) . ?
C23 C36 1.505(13) . ?
C23 C24 1.595(16) . ?
C24 C24A 1.527(17) . ?
C24 H24 1.0000 . ?
C24A C25 1.560(13) . ?
C24A C27B 1.576(15) . ?
C24A H24A 1.0000 . ?
C25 C26 1.553(17) . ?
C25 H25 1.0000 . ?
C26 C27 1.36(2) . ?
C26 H26 0.9500 . ?
C27 C27A 1.518(17) . ?
C27 H27 0.9500 . ?
C27A C27B 1.568(13) . ?
C27B H27B 1.0000 . ?
C28 C29 1.55(2) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.389(4) . ?
C29 C34 1.391(4) . ?
C30 C31 1.390(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.387(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.385(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.390(4) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?

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
C3A O1 C6 95.2(7) . . ?
C7 O2 C9A 97.2(8) . . ?
N2 C1 C9A 112.0(10) . . ?
N2 C1 H1A 109.2 . . ?
C9A C1 H1A 109.2 . . ?
N2 C1 H1B 109.2 . . ?
C9A C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
C1 N2 C10 110.8(14) . . ?
C1 N2 C3 111.9(11) . . ?
C10 N2 C3 109.1(12) . . ?
N2 C3 C3A 108.5(9) . . ?
N2 C3 H3A 110.0 . . ?
C3A C3 H3A 110.0 . . ?
N2 C3 H3B 110.0 . . ?
C3A C3 H3B 110.0 . . ?
H3A C3 H3B 108.4 . . ?
O1 C3A C3 111.6(9) . . ?
O1 C3A C9B 106.8(7) . . ?
C3 C3A C9B 112.9(9) . . ?
O1 C3A C4 98.9(7) . . ?
C3 C3A C4 120.5(9) . . ?
C9B C3A C4 104.6(8) . . ?
C5 C4 C3A 106.0(8) . . ?
C5 C4 C17 129.9(9) . . ?
C3A C4 C17 123.4(8) . . ?
C4 C5 C6 104.5(9) . . ?
C4 C5 C18 131.7(10) . . ?
C6 C5 C18 122.7(9) . . ?
O1 C6 C5 100.8(8) . . ?
O1 C6 C6A 104.9(8) . . ?
C5 C6 C6A 107.3(9) . . ?
O1 C6 H6 114.2 . . ?
C5 C6 H6 114.2 . . ?
C6A C6 H6 114.2 . . ?
C6 C6A C7 116.5(11) . . ?
C6 C6A C9B 99.9(8) . . ?
C7 C6A C9B 99.7(8) . . ?
C6 C6A H6A 113.0 . . ?
C7 C6A H6A 113.0 . . ?
C9B C6A H6A 113.0 . . ?
O2 C7 C8 98.5(10) . . ?
O2 C7 C6A 102.7(8) . . ?
C8 C7 C6A 105.8(9) . . ?
O2 C7 H7 115.9 . . ?
C8 C7 H7 115.9 . . ?
C6A C7 H7 115.9 . . ?
C9 C8 C7 106.7(10) . . ?
C9 C8 H8 126.7 . . ?
C7 C8 H8 126.7 . . ?
C8 C9 C9A 106.6(9) . . ?
C8 C9 H9 126.7 . . ?
C9A C9 H9 126.7 . . ?
O2 C9A C1 111.0(10) . . ?
O2 C9A C9 98.8(8) . . ?
C1 C9A C9 123.5(11) . . ?
O2 C9A C9B 104.1(8) . . ?
C1 C9A C9B 111.8(9) . . ?
C9 C9A C9B 105.4(9) . . ?
C3A C9B C9A 111.1(8) . . ?
C3A C9B C6A 99.0(8) . . ?
C9A C9B C6A 101.7(7) . . ?
C3A C9B H9B 114.5 . . ?
C9A C9B H9B 114.5 . . ?
C6A C9B H9B 114.5 . . ?
N2 C10 C11 112.9(13) . . ?
N2 C10 H10A 109.0 . . ?
C11 C10 H10A 109.0 . . ?
N2 C10 H10B 109.0 . . ?
C11 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C16 C11 C12 113.2(15) . . ?
C16 C11 C10 115.7(19) . . ?
C12 C11 C10 130.9(17) . . ?
C13 C12 C11 124.6(14) . . ?
C13 C12 H12 117.7 . . ?
C11 C12 H12 117.7 . . ?
C14 C13 C12 121.1(17) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 119.2(17) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C14 C15 C16 121.2(17) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C11 C16 C15 119.7(19) . . ?
C11 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
F2 C17 F3 107.7(4) . . ?
F2 C17 F1 107.6(4) . . ?
F3 C17 F1 107.5(4) . . ?
F2 C17 C4 112.5(6) . . ?
F3 C17 C4 110.2(6) . . ?
F1 C17 C4 111.3(6) . . ?
F6 C18 F5 109.0(5) . . ?
F5' C18 F4' 108.2(5) . . ?
F6 C18 F4 108.3(5) . . ?
F5 C18 F4 108.3(4) . . ?
F5' C18 F6' 108.0(5) . . ?
F4' C18 F6' 107.9(5) . . ?
F6 C18 C5 111.8(8) . . ?
F5 C18 C5 107.2(8) . . ?
F5' C18 C5 121.9(14) . . ?
F4' C18 C5 112.2(12) . . ?
F4 C18 C5 112.1(8) . . ?
F6' C18 C5 97.4(13) . . ?
C24 O3 C21A 98.0(8) . . ?
C27A O4 C25 98.4(8) . . ?
C27A C19 N20 112.8(9) . . ?
C27A C19 H19A 109.0 . . ?
N20 C19 H19A 109.0 . . ?
C27A C19 H19B 109.0 . . ?
N20 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
C28 N20 C21 113.2(12) . . ?
C28 N20 C19 110.9(15) . . ?
C21 N20 C19 109.4(10) . . ?
N20 C21 C21A 112.7(9) . . ?
N20 C21 H21A 109.1 . . ?
C21A C21 H21A 109.1 . . ?
N20 C21 H21B 109.1 . . ?
C21A C21 H21B 109.1 . . ?
H21A C21 H21B 107.8 . . ?
O3 C21A C21 112.9(9) . . ?
O3 C21A C22 101.1(8) . . ?
C21 C21A C22 120.8(8) . . ?
O3 C21A C27B 101.3(8) . . ?
C21 C21A C27B 113.1(9) . . ?
C22 C21A C27B 105.2(8) . . ?
C23 C22 C35 131.3(10) . . ?
C23 C22 C21A 106.0(9) . . ?
C35 C22 C21A 122.1(8) . . ?
C22 C23 C36 131.8(10) . . ?
C22 C23 C24 104.6(9) . . ?
C36 C23 C24 123.6(9) . . ?
O3 C24 C24A 103.3(9) . . ?
O3 C24 C23 100.3(9) . . ?
C24A C24 C23 105.1(9) . . ?
O3 C24 H24 115.4 . . ?
C24A C24 H24 115.4 . . ?
C23 C24 H24 115.4 . . ?
C24 C24A C25 116.2(9) . . ?
C24 C24A C27B 100.4(8) . . ?
C25 C24A C27B 99.7(8) . . ?
C24 C24A H24A 113.0 . . ?
C25 C24A H24A 113.0 . . ?
C27B C24A H24A 113.0 . . ?
O4 C25 C26 101.5(9) . . ?
O4 C25 C24A 102.2(8) . . ?
C26 C25 C24A 105.4(8) . . ?
O4 C25 H25 115.3 . . ?
C26 C25 H25 115.3 . . ?
C24A C25 H25 115.3 . . ?
C27 C26 C25 104.4(10) . . ?
C27 C26 H26 127.8 . . ?
C25 C26 H26 127.8 . . ?
C26 C27 C27A 104.3(11) . . ?
C26 C27 H27 127.8 . . ?
C27A C27 H27 127.8 . . ?
O4 C27A C19 114.8(10) . . ?
O4 C27A C27 102.4(10) . . ?
C19 C27A C27 119.8(11) . . ?
O4 C27A C27B 102.5(8) . . ?
C19 C27A C27B 110.5(9) . . ?
C27 C27A C27B 105.0(9) . . ?
C21A C27B C27A 112.4(9) . . ?
C21A C27B C24A 101.3(8) . . ?
C27A C27B C24A 100.5(8) . . ?
C21A C27B H27B 113.7 . . ?
C27A C27B H27B 113.7 . . ?
C24A C27B H27B 113.8 . . ?
N20 C28 C29 114.5(14) . . ?
N20 C28 H28A 108.6 . . ?
C29 C28 H28A 108.6 . . ?
N20 C28 H28B 108.6 . . ?
C29 C28 H28B 108.6 . . ?
H28A C28 H28B 107.6 . . ?
C30 C29 C34 116.6(10) . . ?
C30 C29 C28 120.9(12) . . ?
C34 C29 C28 121.5(12) . . ?
C29 C30 C31 120.7(11) . . ?
C29 C30 H30 119.7 . . ?
C31 C30 H30 119.7 . . ?
C32 C31 C30 120.3(12) . . ?
C32 C31 H31 119.8 . . ?
C30 C31 H31 119.8 . . ?
C33 C32 C31 121.2(13) . . ?
C33 C32 H32 119.4 . . ?
C31 C32 H32 119.4 . . ?
C32 C33 C34 116.3(13) . . ?
C32 C33 H33 121.8 . . ?
C34 C33 H33 121.8 . . ?
C33 C34 C29 124.7(11) . . ?
C33 C34 H34 117.7 . . ?
C29 C34 H34 117.7 . . ?
F7 C35 F8 107.7(4) . . ?
F7 C35 F9 107.8(4) . . ?
F8 C35 F9 107.4(4) . . ?
F7 C35 C22 111.2(6) . . ?
F8 C35 C22 111.7(7) . . ?
F9 C35 C22 110.8(7) . . ?
F11 C36 F10 108.5(5) . . ?
F12' C36 F10' 108.2(5) . . ?
F12' C36 F11' 108.1(5) . . ?
F10' C36 F11' 107.9(5) . . ?
F11 C36 F12 107.8(5) . . ?
F10 C36 F12 107.7(5) . . ?
F11 C36 C23 112.2(8) . . ?
F12' C36 C23 107.7(14) . . ?
F10 C36 C23 106.7(8) . . ?
F10' C36 C23 125.7(15) . . ?
F11' C36 C23 97.9(13) . . ?
F12 C36 C23 113.6(8) . . ?

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
C9A C1 N2 C10 -175.8(11) . . . . ?
C9A C1 N2 C3 62.3(14) . . . . ?
C1 N2 C3 C3A -61.3(15) . . . . ?
C10 N2 C3 C3A 175.8(14) . . . . ?
C6 O1 C3A C3 178.6(9) . . . . ?
C6 O1 C3A C9B 54.8(9) . . . . ?
C6 O1 C3A C4 -53.5(8) . . . . ?
N2 C3 C3A O1 -66.0(13) . . . . ?
N2 C3 C3A C9B 54.3(14) . . . . ?
N2 C3 C3A C4 178.8(10) . . . . ?
O1 C3A C4 C5 34.4(10) . . . . ?
C3 C3A C4 C5 156.1(11) . . . . ?
C9B C3A C4 C5 -75.6(10) . . . . ?
O1 C3A C4 C17 -154.6(8) . . . . ?
C3 C3A C4 C17 -33.0(14) . . . . ?
C9B C3A C4 C17 95.4(10) . . . . ?
C3A C4 C5 C6 0.1(11) . . . . ?
C17 C4 C5 C6 -170.0(9) . . . . ?
C3A C4 C5 C18 167.8(10) . . . . ?
C17 C4 C5 C18 -2.3(19) . . . . ?
C3A O1 C6 C5 55.0(8) . . . . ?
C3A O1 C6 C6A -56.4(9) . . . . ?
C4 C5 C6 O1 -34.7(11) . . . . ?
C18 C5 C6 O1 156.2(9) . . . . ?
C4 C5 C6 C6A 74.8(11) . . . . ?
C18 C5 C6 C6A -94.3(11) . . . . ?
O1 C6 C6A C7 -69.2(11) . . . . ?
C5 C6 C6A C7 -175.8(9) . . . . ?
O1 C6 C6A C9B 36.9(10) . . . . ?
C5 C6 C6A C9B -69.7(10) . . . . ?
C9A O2 C7 C8 -51.9(9) . . . . ?
C9A O2 C7 C6A 56.5(9) . . . . ?
C6 C6A C7 O2 69.9(11) . . . . ?
C9B C6A C7 O2 -36.4(10) . . . . ?
C6 C6A C7 C8 172.7(10) . . . . ?
C9B C6A C7 C8 66.4(11) . . . . ?
O2 C7 C8 C9 33.2(11) . . . . ?
C6A C7 C8 C9 -72.7(12) . . . . ?
C7 C8 C9 C9A 0.5(12) . . . . ?
C7 O2 C9A C1 -176.0(9) . . . . ?
C7 O2 C9A C9 52.9(9) . . . . ?
C7 O2 C9A C9B -55.6(9) . . . . ?
N2 C1 C9A O2 61.4(12) . . . . ?
N2 C1 C9A C9 178.1(10) . . . . ?
N2 C1 C9A C9B -54.4(13) . . . . ?
C8 C9 C9A O2 -33.2(11) . . . . ?
C8 C9 C9A C1 -155.6(11) . . . . ?
C8 C9 C9A C9B 74.2(10) . . . . ?
O1 C3A C9B C9A 74.5(10) . . . . ?
C3 C3A C9B C9A -48.5(11) . . . . ?
C4 C3A C9B C9A 178.7(7) . . . . ?
O1 C3A C9B C6A -31.8(9) . . . . ?
C3 C3A C9B C6A -154.8(9) . . . . ?
C4 C3A C9B C6A 72.4(8) . . . . ?
O2 C9A C9B C3A -73.1(10) . . . . ?
C1 C9A C9B C3A 46.8(12) . . . . ?
C9 C9A C9B C3A -176.5(8) . . . . ?
O2 C9A C9B C6A 31.5(10) . . . . ?
C1 C9A C9B C6A 151.4(10) . . . . ?
C9 C9A C9B C6A -72.0(10) . . . . ?
C6 C6A C9B C3A -3.1(9) . . . . ?
C7 C6A C9B C3A 116.2(8) . . . . ?
C6 C6A C9B C9A -117.0(9) . . . . ?
C7 C6A C9B C9A 2.3(10) . . . . ?
C1 N2 C10 C11 76(2) . . . . ?
C3 N2 C10 C11 -160.5(18) . . . . ?
N2 C10 C11 C16 -141(2) . . . . ?
N2 C10 C11 C12 44(3) . . . . ?
C16 C11 C12 C13 -2(3) . . . . ?
C10 C11 C12 C13 172(2) . . . . ?
C11 C12 C13 C14 -7(3) . . . . ?
C12 C13 C14 C15 11(3) . . . . ?
C13 C14 C15 C16 -7(3) . . . . ?
C12 C11 C16 C15 6(3) . . . . ?
C10 C11 C16 C15 -169(2) . . . . ?
C14 C15 C16 C11 -2(4) . . . . ?
C5 C4 C17 F2 -9.9(13) . . . . ?
C3A C4 C17 F2 -178.5(7) . . . . ?
C5 C4 C17 F3 110.2(11) . . . . ?
C3A C4 C17 F3 -58.4(10) . . . . ?
C5 C4 C17 F1 -130.6(11) . . . . ?
C3A C4 C17 F1 60.7(10) . . . . ?
C4 C5 C18 F6 -165.4(12) . . . . ?
C6 C5 C18 F6 0.5(13) . . . . ?
C4 C5 C18 F5 75.2(14) . . . . ?
C6 C5 C18 F5 -118.9(10) . . . . ?
C4 C5 C18 F5' 35(2) . . . . ?
C6 C5 C18 F5' -159.2(17) . . . . ?
C4 C5 C18 F4' -95.6(19) . . . . ?
C6 C5 C18 F4' 70.3(18) . . . . ?
C4 C5 C18 F4 -43.6(14) . . . . ?
C6 C5 C18 F4 122.3(10) . . . . ?
C4 C5 C18 F6' 151.6(18) . . . . ?
C6 C5 C18 F6' -42.6(17) . . . . ?
C27A C19 N20 C28 175.1(13) . . . . ?
C27A C19 N20 C21 -59.4(14) . . . . ?
C28 N20 C21 C21A -177.6(17) . . . . ?
C19 N20 C21 C21A 58.1(14) . . . . ?
C24 O3 C21A C21 -177.5(9) . . . . ?
C24 O3 C21A C22 52.0(9) . . . . ?
C24 O3 C21A C27B -56.1(9) . . . . ?
N20 C21 C21A O3 60.4(14) . . . . ?
N20 C21 C21A C22 -179.8(11) . . . . ?
N20 C21 C21A C27B -53.9(14) . . . . ?
O3 C21A C22 C23 -32.9(11) . . . . ?
C21 C21A C22 C23 -158.3(12) . . . . ?
C27B C21A C22 C23 72.2(11) . . . . ?
O3 C21A C22 C35 155.7(9) . . . . ?
C21 C21A C22 C35 30.3(15) . . . . ?
C27B C21A C22 C35 -99.2(10) . . . . ?
C35 C22 C23 C36 -10(2) . . . . ?
C21A C22 C23 C36 179.4(12) . . . . ?
C35 C22 C23 C24 171.6(10) . . . . ?
C21A C22 C23 C24 1.2(12) . . . . ?
C21A O3 C24 C24A 57.9(9) . . . . ?
C21A O3 C24 C23 -50.4(10) . . . . ?
C22 C23 C24 O3 31.2(12) . . . . ?
C36 C23 C24 O3 -147.2(10) . . . . ?
C22 C23 C24 C24A -75.7(11) . . . . ?
C36 C23 C24 C24A 105.9(12) . . . . ?
O3 C24 C24A C25 71.2(11) . . . . ?
C23 C24 C24A C25 175.9(9) . . . . ?
O3 C24 C24A C27B -35.1(9) . . . . ?
C23 C24 C24A C27B 69.6(9) . . . . ?
C27A O4 C25 C26 49.5(9) . . . . ?
C27A O4 C25 C24A -59.3(9) . . . . ?
C24 C24A C25 O4 -69.9(11) . . . . ?
C27B C24A C25 O4 36.8(9) . . . . ?
C24 C24A C25 C26 -175.6(10) . . . . ?
C27B C24A C25 C26 -68.9(11) . . . . ?
O4 C25 C26 C27 -29.3(11) . . . . ?
C24A C25 C26 C27 76.9(11) . . . . ?
C25 C26 C27 C27A -2.3(12) . . . . ?
C25 O4 C27A C19 176.7(9) . . . . ?
C25 O4 C27A C27 -51.8(9) . . . . ?
C25 O4 C27A C27B 57.0(9) . . . . ?
N20 C19 C27A O4 -61.3(12) . . . . ?
N20 C19 C27A C27 176.1(10) . . . . ?
N20 C19 C27A C27B 53.9(13) . . . . ?
C26 C27 C27A O4 33.6(11) . . . . ?
C26 C27 C27A C19 162.0(11) . . . . ?
C26 C27 C27A C27B -73.2(11) . . . . ?
O3 C21A C27B C27A -73.4(10) . . . . ?
C21 C21A C27B C27A 47.8(12) . . . . ?
C22 C21A C27B C27A -178.3(8) . . . . ?
O3 C21A C27B C24A 33.0(9) . . . . ?
C21 C21A C27B C24A 154.2(9) . . . . ?
C22 C21A C27B C24A -71.9(8) . . . . ?
O4 C27A C27B C21A 75.2(10) . . . . ?
C19 C27A C27B C21A -47.6(12) . . . . ?
C27 C27A C27B C21A -178.1(10) . . . . ?
O4 C27A C27B C24A -31.8(10) . . . . ?
C19 C27A C27B C24A -154.5(10) . . . . ?
C27 C27A C27B C24A 74.9(11) . . . . ?
C24 C24A C27B C21A 0.7(9) . . . . ?
C25 C24A C27B C21A -118.5(9) . . . . ?
C24 C24A C27B C27A 116.3(8) . . . . ?
C25 C24A C27B C27A -2.8(10) . . . . ?
C21 N20 C28 C29 164.9(17) . . . . ?
C19 N20 C28 C29 -72(2) . . . . ?
N20 C28 C29 C30 -40(3) . . . . ?
N20 C28 C29 C34 152(2) . . . . ?
C34 C29 C30 C31 -1(3) . . . . ?
C28 C29 C30 C31 -170.1(19) . . . . ?
C29 C30 C31 C32 1(3) . . . . ?
C30 C31 C32 C33 -3(3) . . . . ?
C31 C32 C33 C34 4(3) . . . . ?
C32 C33 C34 C29 -4(3) . . . . ?
C30 C29 C34 C33 3(3) . . . . ?
C28 C29 C34 C33 172(2) . . . . ?
C23 C22 C35 F7 -112.9(13) . . . . ?
C21A C22 C35 F7 56.1(11) . . . . ?
C23 C22 C35 F8 7.5(15) . . . . ?
C21A C22 C35 F8 176.5(8) . . . . ?
C23 C22 C35 F9 127.2(12) . . . . ?
C21A C22 C35 F9 -63.8(10) . . . . ?
C22 C23 C36 F11 -167.5(13) . . . . ?
C24 C23 C36 F11 10.4(14) . . . . ?
C22 C23 C36 F12' -78.6(19) . . . . ?
C24 C23 C36 F12' 99.3(17) . . . . ?
C22 C23 C36 F10 73.7(15) . . . . ?
C24 C23 C36 F10 -108.4(12) . . . . ?
C22 C23 C36 F10' 51(2) . . . . ?
C24 C23 C36 F10' -131.5(18) . . . . ?
C22 C23 C36 F11' 169.5(19) . . . . ?
C24 C23 C36 F11' -12.7(18) . . . . ?
C22 C23 C36 F12 -44.8(17) . . . . ?
C24 C23 C36 F12 133.1(10) . . . . ?

_refine_diff_density_max         0.461
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.085

_shelxl_version_number           2014/6


