# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

####################################################################### 
# 
# 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_sad
_database_code_depnum_ccdc_archive 'CCDC 1033310'
_audit_update_record             
;
2014-11-07 deposited with the CCDC.
2016-06-01 downloaded from the CCDC.
;

_audit_creation_date             2013-06-27T09:58:31-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#------------------ CHEMICAL INFORMATION ------------------------------------#

_chemical_formula_moiety         'C21 H5 F10 N1 O1'
_chemical_formula_sum            'C21 H5 F10 N O'
_chemical_formula_weight         477.26

#------------------ UNIT CELL INFORMATION -----------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.495(1)
_cell_length_b                   8.509(1)
_cell_length_c                   16.398(3)
_cell_angle_alpha                91.72(2)
_cell_angle_beta                 101.45(1)
_cell_angle_gamma                116.12(1)
_cell_volume                     912.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    2770
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      25.98

#------------------ CRYSTAL INFORMATION -------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.738
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.857
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   
;
 '(SADABS (Sheldrick, Bruker, 2008))'
;

#------------------ DATA COLLECTION INFORMATION -----------------------------#

_diffrn_ambient_temperature      250(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            25979
_diffrn_reflns_av_R_equivalents  0.1678
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_full        25.98
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_reflns_number_total             3563
_reflns_number_gt                1595
_reflns_threshold_expression     >2sigma(I)

#------------------ COMPUTER PROGRAMS USED ----------------------------------#

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND 3.2i (Crystal Impact GbR 2005)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#------------------ REFINEMENT INFORMATION ----------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0145P)²+1.1243P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3563
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1915
_refine_ls_R_factor_gt           0.0735
_refine_ls_wR_factor_gt          0.097
_refine_ls_wR_factor_ref         0.128
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_restrained_S_all      1.04
_refine_ls_shift/su_max          0
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.236

#------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
_atom_site_disorder_assembly
C1 C 0.0014(7) -0.2121(6) 0.7440(3) 0.0514(12) Uani 1 d . . .
C2 C -0.0200(7) -0.3772(6) 0.7249(3) 0.0599(13) Uani 1 d . . .
H2 H 0.0178 -0.4442 0.7617 0.072 Uiso 1 calc R . .
C3 C -0.1104(7) -0.4262(6) 0.6386(3) 0.0629(14) Uani 1 d . . .
H3 H -0.1431 -0.5322 0.6073 0.075 Uiso 1 calc R . .
C4 C -0.1417(6) -0.2907(6) 0.6091(3) 0.0515(12) Uani 1 d . . .
C5 C -0.2284(7) -0.2638(6) 0.5280(3) 0.0595(13) Uani 1 d . . .
H5 H -0.2787 -0.3542 0.4836 0.071 Uiso 1 calc R . .
C6 C -0.2405(6) -0.1131(6) 0.5128(3) 0.0552(12) Uani 1 d . . .
H6 H -0.1865 -0.0256 0.5587 0.066 Uiso 1 calc R . .
C7 C -0.3275(6) -0.0688(6) 0.4336(3) 0.0521(12) Uani 1 d . . .
C8 C -0.3265(7) 0.0946(6) 0.4310(3) 0.0555(12) Uani 1 d . . .
C9 C -0.4079(7) 0.1473(7) 0.3606(3) 0.0609(13) Uani 1 d . . .
C10 C -0.4973(7) 0.0308(7) 0.2873(3) 0.0614(13) Uani 1 d . . .
C11 C -0.5036(7) -0.1327(7) 0.2862(3) 0.0580(13) Uani 1 d . . .
C12 C -0.4192(7) -0.1799(6) 0.3577(3) 0.0527(12) Uani 1 d . . .
C13 C 0.0874(6) -0.0960(6) 0.8220(3) 0.0477(11) Uani 1 d . . .
H13 H 0.135 -0.1405 0.8678 0.057 Uiso 1 calc R . .
C14 C 0.1088(6) 0.0688(6) 0.8381(3) 0.0470(11) Uani 1 d . . .
C15 C 0.0437(7) 0.1568(6) 0.7739(3) 0.0532(12) Uani 1 d . . .
C16 C 0.2057(7) 0.1706(5) 0.9240(3) 0.0480(11) Uani 1 d . . .
C17 C 0.3928(7) 0.1897(6) 0.9697(3) 0.0504(12) Uani 1 d . . .
C18 C 0.4837(8) 0.2856(6) 1.0481(3) 0.0568(13) Uani 1 d . . .
C19 C 0.3900(8) 0.3670(6) 1.0843(3) 0.0560(13) Uani 1 d . . .
C20 C 0.2070(7) 0.3529(6) 1.0413(3) 0.0530(12) Uani 1 d . . .
C21 C 0.1161(7) 0.2540(6) 0.9626(3) 0.0505(12) Uani 1 d . . .
F1 F -0.2389(4) 0.2129(3) 0.50192(16) 0.0778(9) Uani 1 d . . .
F2 F -0.3991(5) 0.3079(4) 0.36198(18) 0.0857(9) Uani 1 d . . .
F3 F -0.5790(5) 0.0780(4) 0.21715(17) 0.0868(9) Uani 1 d . . .
F4 F -0.5936(4) -0.2480(4) 0.21506(16) 0.0828(9) Uani 1 d . . .
F5 F -0.4282(4) -0.3419(3) 0.35207(15) 0.0689(8) Uani 1 d . . .
F6 F 0.4932(4) 0.1152(4) 0.93694(15) 0.0679(8) Uani 1 d . . .
F7 F 0.6685(4) 0.3066(4) 1.08936(16) 0.0830(9) Uani 1 d . . .
F8 F 0.4813(5) 0.4621(4) 1.16085(16) 0.0865(10) Uani 1 d . . .
F9 F 0.1138(4) 0.4319(4) 1.07515(17) 0.0811(9) Uani 1 d . . .
F10 F -0.0656(4) 0.2395(4) 0.92267(17) 0.0778(9) Uani 1 d . . .
N1 N -0.0059(7) 0.2297(5) 0.7236(3) 0.0768(13) Uani 1 d . . .
O1 O -0.0735(4) -0.1557(4) 0.67373(17) 0.0516(8) Uani 1 d . . .



#------------------ MOLECULAR GEOMETRY --------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.361(6) . ?
C1 O1 1.374(5) . ?
C1 C13 1.436(5) . ?
C2 C3 1.404(6) . ?
C2 H2 0.93 . ?
C3 C4 1.358(6) . ?
C3 H3 0.93 . ?
C4 O1 1.378(5) . ?
C4 C5 1.431(6) . ?
C5 C6 1.351(6) . ?
C5 H5 0.93 . ?
C6 C7 1.471(6) . ?
C6 H6 0.93 . ?
C7 C8 1.389(6) . ?
C7 C12 1.391(6) . ?
C8 F1 1.358(5) . ?
C8 C9 1.377(6) . ?
C9 F2 1.339(5) . ?
C9 C10 1.379(6) . ?
C10 F3 1.350(5) . ?
C10 C11 1.371(6) . ?
C11 F4 1.347(5) . ?
C11 C12 1.375(6) . ?
C12 F5 1.350(5) . ?
C13 C14 1.351(5) . ?
C13 H13 0.93 . ?
C14 C15 1.439(6) . ?
C14 C16 1.494(5) . ?
C15 N1 1.147(5) . ?
C16 C21 1.383(6) . ?
C16 C17 1.390(6) . ?
C17 F6 1.348(5) . ?
C17 C18 1.372(6) . ?
C18 F7 1.345(5) . ?
C18 C19 1.377(6) . ?
C19 F8 1.344(5) . ?
C19 C20 1.364(6) . ?
C20 F9 1.339(5) . ?
C20 C21 1.386(6) . ?
C21 F10 1.338(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 O1 110.4(4) . . ?
C2 C1 C13 130.9(4) . . ?
O1 C1 C13 118.7(4) . . ?
C1 C2 C3 106.4(4) . . ?
C1 C2 H2 126.8 . . ?
C3 C2 H2 126.8 . . ?
C4 C3 C2 107.6(4) . . ?
C4 C3 H3 126.2 . . ?
C2 C3 H3 126.2 . . ?
C3 C4 O1 109.6(4) . . ?
C3 C4 C5 133.5(4) . . ?
O1 C4 C5 116.9(4) . . ?
C6 C5 C4 123.0(4) . . ?
C6 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
C5 C6 C7 128.8(4) . . ?
C5 C6 H6 115.6 . . ?
C7 C6 H6 115.6 . . ?
C8 C7 C12 114.3(4) . . ?
C8 C7 C6 120.1(4) . . ?
C12 C7 C6 125.6(4) . . ?
F1 C8 C9 116.7(4) . . ?
F1 C8 C7 118.7(4) . . ?
C9 C8 C7 124.6(4) . . ?
F2 C9 C8 121.6(5) . . ?
F2 C9 C10 120.0(5) . . ?
C8 C9 C10 118.3(5) . . ?
F3 C10 C11 120.4(4) . . ?
F3 C10 C9 119.9(5) . . ?
C11 C10 C9 119.7(5) . . ?
F4 C11 C10 119.9(4) . . ?
F4 C11 C12 119.9(4) . . ?
C10 C11 C12 120.2(4) . . ?
F5 C12 C11 117.2(4) . . ?
F5 C12 C7 119.8(4) . . ?
C11 C12 C7 122.9(5) . . ?
C14 C13 C1 129.0(4) . . ?
C14 C13 H13 115.5 . . ?
C1 C13 H13 115.5 . . ?
C13 C14 C15 122.4(4) . . ?
C13 C14 C16 121.2(4) . . ?
C15 C14 C16 116.5(4) . . ?
N1 C15 C14 178.8(5) . . ?
C21 C16 C17 115.8(4) . . ?
C21 C16 C14 122.1(4) . . ?
C17 C16 C14 122.1(4) . . ?
F6 C17 C18 117.7(4) . . ?
F6 C17 C16 120.2(4) . . ?
C18 C17 C16 122.1(4) . . ?
F7 C18 C17 120.5(4) . . ?
F7 C18 C19 119.1(4) . . ?
C17 C18 C19 120.3(4) . . ?
F8 C19 C20 120.8(4) . . ?
F8 C19 C18 119.8(4) . . ?
C20 C19 C18 119.4(4) . . ?
F9 C20 C19 120.4(4) . . ?
F9 C20 C21 120.0(4) . . ?
C19 C20 C21 119.6(4) . . ?
F10 C21 C16 119.2(4) . . ?
F10 C21 C20 118.1(4) . . ?
C16 C21 C20 122.7(4) . . ?
C1 O1 C4 106.0(3) . . ?

####################################################################### 
# 
# 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_sads1s3
_database_code_depnum_ccdc_archive 'CCDC 1033328'
_audit_update_record             
;
2014-11-07 deposited with the CCDC.
2016-06-01 downloaded from the CCDC.
;

_audit_creation_date             2013-04-11T16:33:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#------------------ CHEMICAL INFORMATION ------------------------------------#

_chemical_formula_moiety         'C14 H4 F5 N1 O2'
_chemical_formula_sum            'C14 H4 F5 N O2'
_chemical_formula_weight         313.18
_chemical_absolute_configuration unk

#------------------ UNIT CELL INFORMATION -----------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.414(2)
_cell_length_b                   12.582(1)
_cell_length_c                   13.338(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.00(2)
_cell_angle_gamma                90
_cell_volume                     1244.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4867
_cell_measurement_theta_min      3.17
_cell_measurement_theta_max      27.52

#------------------ CRYSTAL INFORMATION -------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_exptl_crystal_density_diffrn    1.672
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.834
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   
;
 '(SADABS (Sheldrick, Bruker, 2008))'
;

#------------------ DATA COLLECTION INFORMATION -----------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            12916
_diffrn_reflns_av_R_equivalents  0.0706
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.17
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_full        27.52
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_reflns_number_total             2942
_reflns_number_gt                1697
_reflns_threshold_expression     >2sigma(I)

#------------------ COMPUTER PROGRAMS USED ----------------------------------#

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND 3.2i (Crystal Impact GbR 2005)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#------------------ REFINEMENT INFORMATION ----------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
Because of insufficient anomalous scattering effets (only C, H, N, O atoms in
the structure and data collected with MoKa radiation), Friedel pairs have
been merged with MERG4 instruction, that is why the Flack parameter is not
here reported.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0871P)²+1.5846P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2942
_refine_ls_number_parameters     397
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1418
_refine_ls_R_factor_gt           0.0734
_refine_ls_wR_factor_gt          0.1706
_refine_ls_wR_factor_ref         0.2047
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.287

#------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
_atom_site_disorder_assembly
C1 C 0.224(2) 0.1424(11) 0.3147(9) 0.090(4) Uani 1 d . . .
H1 H 0.1927 0.1555 0.248 0.108 Uiso 1 calc R . .
C2 C 0.0770(15) 0.1344(8) 0.3861(7) 0.065(3) Uani 1 d . . .
C3 C -0.1043(17) 0.1412(8) 0.3755(8) 0.077(3) Uani 1 d . . .
H3 H -0.1671 0.1523 0.3155 0.092 Uiso 1 calc R . .
C4 C -0.1810(13) 0.1289(7) 0.4683(7) 0.057(2) Uani 1 d . . .
H4 H -0.3029 0.1299 0.4835 0.068 Uiso 1 calc R . .
C5 C -0.0379(10) 0.1149(7) 0.5331(6) 0.0476(19) Uani 1 d . . .
C6 C -0.0359(11) 0.0986(7) 0.6395(6) 0.0457(18) Uani 1 d . . .
H6 H -0.1479 0.0955 0.6697 0.055 Uiso 1 calc R . .
C7 C 0.1112(11) 0.0871(6) 0.7018(6) 0.0455(18) Uani 1 d . . .
C8 C 0.2903(12) 0.1000(7) 0.6670(5) 0.0459(19) Uani 1 d . . .
C9 C 0.0953(10) 0.0553(6) 0.8071(6) 0.0453(19) Uani 1 d . . .
C10 C 0.0165(11) -0.0371(8) 0.8356(6) 0.056(2) Uani 1 d . . .
C11 C 0.0040(13) -0.0702(8) 0.9354(7) 0.061(2) Uani 1 d . . .
C12 C 0.0732(13) -0.0040(9) 1.0083(8) 0.067(3) Uani 1 d . . .
C13 C 0.1599(12) 0.0918(9) 0.9830(6) 0.059(2) Uani 1 d . . .
C14 C 0.1673(11) 0.1174(6) 0.8851(6) 0.0455(18) Uani 1 d . . .
C15 C 0.3786(13) 0.7816(9) -0.1666(6) 0.063(2) Uani 1 d . . .
H15 H 0.3887 0.7926 -0.2353 0.075 Uiso 1 calc R . .
C16 C 0.4565(11) 0.8628(7) -0.0986(5) 0.050(2) Uani 1 d . . .
C17 C 0.5340(12) 0.9534(8) -0.1188(6) 0.053(2) Uani 1 d . . .
H17 H 0.5525 0.9817 -0.1822 0.063 Uiso 1 calc R . .
C18 C 0.5862(11) 1.0021(7) -0.0225(6) 0.050(2) Uani 1 d . . .
H18 H 0.6465 1.0659 -0.0113 0.06 Uiso 1 calc R . .
C19 C 0.5251(10) 0.9312(6) 0.0465(5) 0.0432(18) Uani 1 d . . .
C20 C 0.5379(10) 0.9352(6) 0.1535(5) 0.0417(17) Uani 1 d . . .
H20 H 0.6024 0.992 0.1807 0.05 Uiso 1 calc R . .
C21 C 0.4659(9) 0.8648(6) 0.2213(5) 0.0393(16) Uani 1 d . . .
C22 C 0.3521(11) 0.7765(7) 0.1891(5) 0.0438(19) Uani 1 d . . .
C23 C 0.5080(9) 0.8734(6) 0.3288(5) 0.0407(16) Uani 1 d . . .
C24 C 0.3713(9) 0.8743(7) 0.3999(5) 0.0435(17) Uani 1 d . . .
C25 C 0.4045(10) 0.8759(7) 0.5005(5) 0.0419(17) Uani 1 d . . .
C26 C 0.5828(11) 0.8765(7) 0.5349(5) 0.0479(18) Uani 1 d . . .
C27 C 0.7190(10) 0.8745(7) 0.4700(6) 0.0449(17) Uani 1 d . . .
C28 C 0.6816(9) 0.8720(7) 0.3665(5) 0.0436(17) Uani 1 d . . .
F1 F -0.0535(9) -0.1058(5) 0.7660(4) 0.0869(19) Uani 1 d . . .
F2 F -0.0721(9) -0.1595(5) 0.9615(5) 0.091(2) Uani 1 d . . .
F3 F 0.0633(9) -0.0299(6) 1.1079(4) 0.096(2) Uani 1 d . . .
F4 F 0.2330(9) 0.1517(5) 1.0567(4) 0.0860(19) Uani 1 d . . .
F5 F 0.2481(8) 0.2095(4) 0.8623(4) 0.0733(16) Uani 1 d . . .
F6 F 0.1968(5) 0.8742(5) 0.3664(3) 0.0647(14) Uani 1 d . . .
F7 F 0.2698(6) 0.8812(5) 0.5666(3) 0.0670(14) Uani 1 d . . .
F8 F 0.6197(7) 0.8799(5) 0.6347(3) 0.0669(14) Uani 1 d . . .
F9 F 0.8916(6) 0.8698(5) 0.5040(4) 0.0635(13) Uani 1 d . . .
F10 F 0.8216(5) 0.8678(5) 0.3056(3) 0.0650(14) Uani 1 d . . .
N1 N 0.4403(11) 0.1076(7) 0.6449(6) 0.065(2) Uani 1 d . . .
N2 N 0.2629(11) 0.7057(7) 0.1685(6) 0.067(2) Uani 1 d . . .
O1 O 0.1213(7) 0.1198(5) 0.4841(4) 0.0518(14) Uani 1 d . . .
O2 O 0.3837(16) 0.1334(8) 0.3358(7) 0.106(3) Uani 1 d . . .
O3 O 0.4464(7) 0.8426(4) 0.0025(4) 0.0478(13) Uani 1 d . . .
O4 O 0.3024(11) 0.7017(6) -0.1394(5) 0.075(2) Uani 1 d . . .



#------------------ MOLECULAR GEOMETRY --------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.219(16) . ?
C1 C2 1.462(17) . ?
C1 H1 0.93 . ?
C2 C3 1.352(15) . ?
C2 O1 1.353(10) . ?
C3 C4 1.380(14) . ?
C3 H3 0.93 . ?
C4 C5 1.368(12) . ?
C4 H4 0.93 . ?
C5 O1 1.361(10) . ?
C5 C6 1.434(11) . ?
C6 C7 1.367(11) . ?
C6 H6 0.93 . ?
C7 C8 1.423(12) . ?
C7 C9 1.467(11) . ?
C8 N1 1.159(11) . ?
C9 C10 1.358(12) . ?
C9 C14 1.399(11) . ?
C10 F1 1.364(10) . ?
C10 C11 1.400(13) . ?
C11 F2 1.308(11) . ?
C11 C12 1.372(15) . ?
C12 F3 1.372(11) . ?
C12 C13 1.410(15) . ?
C13 F4 1.345(11) . ?
C13 C14 1.348(11) . ?
C14 F5 1.342(9) . ?
C15 O4 1.212(12) . ?
C15 C16 1.478(13) . ?
C15 H15 0.93 . ?
C16 C17 1.306(13) . ?
C16 O3 1.376(9) . ?
C17 C18 1.468(12) . ?
C17 H17 0.93 . ?
C18 C19 1.364(11) . ?
C18 H18 0.93 . ?
C19 O3 1.384(9) . ?
C19 C20 1.430(11) . ?
C20 C21 1.380(10) . ?
C20 H20 0.93 . ?
C21 C22 1.455(11) . ?
C21 C23 1.465(10) . ?
C22 N2 1.140(10) . ?
C23 C28 1.374(10) . ?
C23 C24 1.400(10) . ?
C24 C25 1.360(9) . ?
C24 F6 1.362(8) . ?
C25 F7 1.345(8) . ?
C25 C26 1.392(10) . ?
C26 C27 1.341(11) . ?
C26 F8 1.356(8) . ?
C27 F9 1.351(9) . ?
C27 C28 1.404(10) . ?
C28 F10 1.329(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 C2 125.1(11) . . ?
O2 C1 H1 117.5 . . ?
C2 C1 H1 117.5 . . ?
C3 C2 O1 109.5(9) . . ?
C3 C2 C1 132.6(10) . . ?
O1 C2 C1 117.9(10) . . ?
C2 C3 C4 108.9(9) . . ?
C2 C3 H3 125.6 . . ?
C4 C3 H3 125.6 . . ?
C5 C4 C3 104.7(9) . . ?
C5 C4 H4 127.7 . . ?
C3 C4 H4 127.7 . . ?
O1 C5 C4 111.1(7) . . ?
O1 C5 C6 119.2(6) . . ?
C4 C5 C6 129.6(8) . . ?
C7 C6 C5 127.7(7) . . ?
C7 C6 H6 116.2 . . ?
C5 C6 H6 116.2 . . ?
C6 C7 C8 121.9(7) . . ?
C6 C7 C9 122.3(7) . . ?
C8 C7 C9 115.8(7) . . ?
N1 C8 C7 175.2(8) . . ?
C10 C9 C14 115.5(7) . . ?
C10 C9 C7 122.9(8) . . ?
C14 C9 C7 121.5(7) . . ?
C9 C10 F1 120.8(7) . . ?
C9 C10 C11 123.8(9) . . ?
F1 C10 C11 115.4(8) . . ?
F2 C11 C12 119.4(9) . . ?
F2 C11 C10 123.0(10) . . ?
C12 C11 C10 117.6(9) . . ?
F3 C12 C11 121.1(10) . . ?
F3 C12 C13 117.8(10) . . ?
C11 C12 C13 121.1(8) . . ?
F4 C13 C14 123.5(9) . . ?
F4 C13 C12 119.0(8) . . ?
C14 C13 C12 117.5(9) . . ?
F5 C14 C13 116.8(8) . . ?
F5 C14 C9 118.7(7) . . ?
C13 C14 C9 124.5(8) . . ?
O4 C15 C16 124.7(8) . . ?
O4 C15 H15 117.7 . . ?
C16 C15 H15 117.7 . . ?
C17 C16 O3 113.3(8) . . ?
C17 C16 C15 130.2(8) . . ?
O3 C16 C15 116.6(8) . . ?
C16 C17 C18 107.1(7) . . ?
C16 C17 H17 126.5 . . ?
C18 C17 H17 126.5 . . ?
C19 C18 C17 103.4(7) . . ?
C19 C18 H18 128.3 . . ?
C17 C18 H18 128.3 . . ?
C18 C19 O3 112.5(7) . . ?
C18 C19 C20 129.3(8) . . ?
O3 C19 C20 118.1(6) . . ?
C21 C20 C19 127.7(7) . . ?
C21 C20 H20 116.1 . . ?
C19 C20 H20 116.1 . . ?
C20 C21 C22 121.7(6) . . ?
C20 C21 C23 121.0(6) . . ?
C22 C21 C23 117.2(6) . . ?
N2 C22 C21 176.8(8) . . ?
C28 C23 C24 115.9(6) . . ?
C28 C23 C21 122.6(6) . . ?
C24 C23 C21 121.3(6) . . ?
C25 C24 F6 118.6(6) . . ?
C25 C24 C23 123.3(6) . . ?
F6 C24 C23 118.2(6) . . ?
F7 C25 C24 121.6(7) . . ?
F7 C25 C26 119.7(6) . . ?
C24 C25 C26 118.6(7) . . ?
C27 C26 F8 119.6(7) . . ?
C27 C26 C25 120.6(7) . . ?
F8 C26 C25 119.9(7) . . ?
C26 C27 F9 120.2(7) . . ?
C26 C27 C28 119.8(7) . . ?
F9 C27 C28 119.9(7) . . ?
F10 C28 C23 120.9(6) . . ?
F10 C28 C27 117.3(6) . . ?
C23 C28 C27 121.8(6) . . ?
C2 O1 C5 105.8(7) . . ?
C16 O3 C19 103.7(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_sad
_database_code_depnum_ccdc_archive 'CCDC 1440461'
_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2016-06-01 downloaded from the CCDC.
;

_audit_creation_date             2015-03-31T10:04:49-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#------------------ CHEMICAL INFORMATION ------------------------------------#

_chemical_formula_moiety         'C13 H5 F5 O2'
_chemical_formula_sum            'C13 H5 F5 O2'
_chemical_formula_weight         288.17
_chemical_absolute_configuration ad

#------------------ UNIT CELL INFORMATION -----------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.634(2)
_cell_length_b                   4.733(2)
_cell_length_c                   18.468(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.01(3)
_cell_angle_gamma                90
_cell_volume                     579.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1488
_cell_measurement_theta_min      4.42
_cell_measurement_theta_max      26.61

#------------------ CRYSTAL INFORMATION -------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.842
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   
;
 '(SADABS (Sheldrick, Bruker, 2008))'
;

#------------------ DATA COLLECTION INFORMATION -----------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            5878
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.42
_diffrn_reflns_theta_max         26.61
_diffrn_reflns_theta_full        26
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.973
_reflns_number_total             2266
_reflns_number_gt                1395
_reflns_threshold_expression     >2sigma(I)

#------------------ COMPUTER PROGRAMS USED ----------------------------------#

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND 3.2i (Crystal Impact GbR 2005)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#------------------ REFINEMENT INFORMATION ----------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0490P)²+0.0659P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.071(8)
_refine_ls_number_reflns         2266
_refine_ls_number_parameters     182
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1208
_refine_ls_R_factor_gt           0.0591
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1239
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.4(13)
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.178

#------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
_atom_site_disorder_assembly
C1 C 0.6300(6) 0.2128(9) 0.0538(2) 0.0535(11) Uani 1 d . . .
H1 H 0.6713 0.095 0.0169 0.064 Uiso 1 calc R . .
C2 C 0.7838(5) 0.3798(8) 0.08975(19) 0.0422(9) Uani 1 d . . .
C3 C 0.9854(5) 0.3781(10) 0.0847(2) 0.0485(10) Uani 1 d . . .
H3 H 1.0591 0.2702 0.0529 0.058 Uiso 1 calc R . .
C4 C 1.0641(6) 0.5705(9) 0.1365(2) 0.0530(10) Uani 1 d . . .
H4 H 1.1995 0.6138 0.1454 0.064 Uiso 1 calc R . .
C5 C 0.9050(6) 0.6805(9) 0.1711(2) 0.0482(10) Uani 1 d . . .
C6 C 0.8919(6) 0.8870(9) 0.2277(2) 0.0509(10) Uani 1 d . . .
H6 H 1.0111 0.9473 0.2508 0.061 Uiso 1 calc R . .
C7 C 0.7176(6) 0.9983(8) 0.2494(2) 0.0467(10) Uani 1 d . . .
H7 H 0.6005 0.9346 0.2255 0.056 Uiso 1 calc R . .
C8 C 0.6920(6) 1.2084(9) 0.3062(2) 0.0499(10) Uani 1 d . . .
C9 C 0.8369(7) 1.2868(8) 0.3599(2) 0.0592(12) Uani 1 d . . .
C10 C 0.8035(10) 1.4856(9) 0.4117(3) 0.0688(14) Uani 1 d . . .
C11 C 0.6210(11) 1.6197(9) 0.4122(3) 0.0742(16) Uani 1 d . . .
C12 C 0.4720(8) 1.5541(11) 0.3607(3) 0.0732(14) Uani 1 d . . .
C13 C 0.5077(7) 1.3504(10) 0.3097(3) 0.0630(13) Uani 1 d . . .
F1 F 1.0161(4) 1.1577(6) 0.36262(14) 0.0807(9) Uani 1 d . . .
F2 F 0.9455(6) 1.5525(7) 0.46130(16) 0.1030(10) Uani 1 d . . .
F3 F 0.5830(5) 1.8205(6) 0.46166(15) 0.1047(12) Uani 1 d . . .
F4 F 0.2924(5) 1.6895(7) 0.3585(2) 0.1197(13) Uani 1 d . . .
F5 F 0.3615(4) 1.2921(7) 0.25974(17) 0.0926(10) Uani 1 d . . .
O1 O 0.7292(4) 0.5671(5) 0.14282(13) 0.0448(7) Uani 1 d . . .
O2 O 0.4522(4) 0.2088(8) 0.06652(17) 0.0714(9) Uani 1 d . . .



#------------------ MOLECULAR GEOMETRY --------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.211(4) . ?
C1 C2 1.435(5) . ?
C1 H1 0.93 . ?
C2 C3 1.344(5) . ?
C2 O1 1.379(4) . ?
C3 C4 1.408(6) . ?
C3 H3 0.93 . ?
C4 C5 1.357(5) . ?
C4 H4 0.93 . ?
C5 O1 1.371(4) . ?
C5 C6 1.436(6) . ?
C6 C7 1.344(5) . ?
C6 H6 0.93 . ?
C7 C8 1.461(6) . ?
C7 H7 0.93 . ?
C8 C13 1.399(6) . ?
C8 C9 1.406(6) . ?
C9 F1 1.336(5) . ?
C9 C10 1.366(6) . ?
C10 F2 1.329(6) . ?
C10 C11 1.367(7) . ?
C11 F3 1.348(5) . ?
C11 C12 1.383(7) . ?
C12 F4 1.352(6) . ?
C12 C13 1.375(7) . ?
C13 F5 1.343(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 C2 127.0(4) . . ?
O2 C1 H1 116.5 . . ?
C2 C1 H1 116.5 . . ?
C3 C2 O1 109.9(3) . . ?
C3 C2 C1 131.1(4) . . ?
O1 C2 C1 118.8(3) . . ?
C2 C3 C4 107.2(3) . . ?
C2 C3 H3 126.4 . . ?
C4 C3 H3 126.4 . . ?
C5 C4 C3 107.0(3) . . ?
C5 C4 H4 126.5 . . ?
C3 C4 H4 126.5 . . ?
C4 C5 O1 109.6(3) . . ?
C4 C5 C6 132.2(4) . . ?
O1 C5 C6 118.2(3) . . ?
C7 C6 C5 123.9(4) . . ?
C7 C6 H6 118 . . ?
C5 C6 H6 118 . . ?
C6 C7 C8 127.1(4) . . ?
C6 C7 H7 116.4 . . ?
C8 C7 H7 116.4 . . ?
C13 C8 C9 114.7(4) . . ?
C13 C8 C7 118.9(4) . . ?
C9 C8 C7 126.3(4) . . ?
F1 C9 C10 117.1(5) . . ?
F1 C9 C8 119.4(4) . . ?
C10 C9 C8 123.5(4) . . ?
F2 C10 C9 121.2(5) . . ?
F2 C10 C11 119.4(5) . . ?
C9 C10 C11 119.4(5) . . ?
F3 C11 C10 121.2(6) . . ?
F3 C11 C12 118.5(5) . . ?
C10 C11 C12 120.2(5) . . ?
F4 C12 C13 119.0(6) . . ?
F4 C12 C11 121.5(5) . . ?
C13 C12 C11 119.5(5) . . ?
F5 C13 C12 118.5(5) . . ?
F5 C13 C8 118.8(4) . . ?
C12 C13 C8 122.7(5) . . ?
C5 O1 C2 106.4(3) . . ?

