# 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 2019

####################################################################### 
# 
# 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_compound1
_database_code_depnum_ccdc_archive 'CCDC 1583010'
loop_
_audit_author_name
_audit_author_address
'Angel Alvarez-Larena' 'Universidad Aut?noma de Barcelona'
_audit_update_record             
;
2017-10-30 deposited with the CCDC.	2019-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
;
4-nitrobenzyl 2,3,4,5,6-pentafluorophenyl sulfide
;
_chemical_formula_moiety         'C13 H6 F5 N O2 S'
_chemical_formula_sum            'C13 H6 F5 N O2 S'
_chemical_formula_weight         335.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.0477(4)
_cell_length_b                   6.1732(5)
_cell_length_c                   41.665(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1298.30(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2203
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      22.46

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.715
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.640
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.317
_shelx_estimated_absorpt_T_min   0.823
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.908
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'SADABS, 2.05'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker SMART-APEX diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.13
_diffrn_reflns_number            10392
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -54
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_theta_min         1.955
_diffrn_reflns_theta_max         28.726
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3149
_reflns_number_gt                2194
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.622
_reflns_Friedel_fraction_max     0.905
_reflns_Friedel_fraction_full    1.000

_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       'SMART 5.6 (Bruker)'
_computing_cell_refinement       'SAINT 5.0 (Bruker)'
_computing_data_reduction        'SAINT 5.0 (Bruker)'
_computing_structure_solution    'SHELXTL-NT 6.1 (Bruker)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0470P)²+0.2681P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_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 648 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(5)
_chemical_absolute_configuration .
_refine_ls_number_reflns         3149
_refine_ls_number_parameters     199
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1122
_refine_ls_wR_factor_gt          0.1006
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
C1 C 0.6826(6) 0.0801(5) 0.16469(7) 0.0453(9) Uani 1 1 d D . . . .
C2 C 0.5407(6) -0.1102(5) 0.16303(8) 0.0519(9) Uani 1 1 d D . . . .
C3 C 0.3449(7) -0.1601(6) 0.18487(8) 0.0614(11) Uani 1 1 d D . . . .
C4 C 0.2887(8) -0.0163(6) 0.20921(8) 0.0661(13) Uani 1 1 d D . . . .
C5 C 0.4258(7) 0.1759(7) 0.21154(8) 0.0655(12) Uani 1 1 d D . . . .
C6 C 0.6212(7) 0.2200(6) 0.18938(8) 0.0560(10) Uani 1 1 d D . . . .
C7 C 0.7687(8) 0.2438(7) 0.10286(8) 0.0534(10) Uani 1 1 d . . . . .
H7A H 0.687230 0.127034 0.090814 0.064 Uiso 1 1 calc R U . . .
H7B H 0.631428 0.344530 0.109424 0.064 Uiso 1 1 calc R U . . .
C8 C 0.9729(6) 0.3571(6) 0.08280(7) 0.0411(8) Uani 1 1 d . . . . .
C9 C 1.0633(8) 0.5602(6) 0.09173(8) 0.0519(9) Uani 1 1 d . . . . .
H9 H 0.991870 0.626625 0.109801 0.062 Uiso 1 1 calc R U . . .
C10 C 1.2559(7) 0.6659(6) 0.07447(8) 0.0486(9) Uani 1 1 d . . . . .
H10 H 1.315145 0.802334 0.080627 0.058 Uiso 1 1 calc R U . . .
C11 C 1.3589(6) 0.5643(5) 0.04784(7) 0.0365(7) Uani 1 1 d . . . . .
C12 C 1.2738(7) 0.3637(6) 0.03802(8) 0.0433(8) Uani 1 1 d . . . . .
H12 H 1.345833 0.298199 0.019912 0.052 Uiso 1 1 calc R U . . .
C13 C 1.0784(7) 0.2612(6) 0.05567(7) 0.0455(9) Uani 1 1 d . . . . .
H13 H 1.017172 0.125939 0.049205 0.055 Uiso 1 1 calc R U . . .
F2 F 0.5861(6) -0.2513(4) 0.13957(7) 0.0929(9) Uani 1 1 d . . . . .
F3 F 0.2080(6) -0.3415(5) 0.18215(9) 0.1147(11) Uani 1 1 d . . . . .
F4 F 0.0983(6) -0.0616(6) 0.23011(6) 0.1126(12) Uani 1 1 d . . . . .
F5 F 0.3728(7) 0.3102(6) 0.23526(7) 0.1216(13) Uani 1 1 d . . . . .
F6 F 0.7513(6) 0.4055(5) 0.19274(8) 0.1016(10) Uani 1 1 d . . . . .
N1 N 1.5704(6) 0.6740(5) 0.02970(7) 0.0446(7) Uani 1 1 d . . . . .
O1 O 1.6685(5) 0.5800(5) 0.00699(6) 0.0592(7) Uani 1 1 d . . . . .
O2 O 1.6383(6) 0.8552(5) 0.03861(7) 0.0642(8) Uani 1 1 d . . . . .
S1 S 0.9418(2) 0.1377(2) 0.13772(2) 0.0673(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
C1 C2 1.3778(13) . ?
C1 C6 1.3785(13) . ?
C1 S1 1.761(3) . ?
C2 F2 1.329(4) . ?
C2 C3 1.3781(13) . ?
C3 F3 1.321(4) . ?
C3 C4 1.3774(13) . ?
C4 F4 1.327(4) . ?
C4 C5 1.3771(13) . ?
C5 F5 1.317(4) . ?
C5 C6 1.3780(13) . ?
C6 F6 1.327(4) . ?
C7 C8 1.500(5) . ?
C7 S1 1.817(4) . ?
C8 C13 1.383(5) . ?
C8 C9 1.385(5) . ?
C9 C10 1.374(5) . ?
C10 C11 1.377(5) . ?
C11 C12 1.373(5) . ?
C11 N1 1.473(4) . ?
C12 C13 1.384(5) . ?
N1 O1 1.216(4) . ?
N1 O2 1.228(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 C6 117.1(3) . . ?
C2 C1 S1 121.8(2) . . ?
C6 C1 S1 121.1(2) . . ?
F2 C2 C1 120.4(3) . . ?
F2 C2 C3 117.6(3) . . ?
C1 C2 C3 122.0(3) . . ?
F3 C3 C4 120.1(3) . . ?
F3 C3 C2 120.5(3) . . ?
C4 C3 C2 119.4(3) . . ?
F4 C4 C5 120.0(3) . . ?
F4 C4 C3 119.8(3) . . ?
C5 C4 C3 120.2(3) . . ?
F5 C5 C4 119.5(3) . . ?
F5 C5 C6 121.6(3) . . ?
C4 C5 C6 118.9(3) . . ?
F6 C6 C5 117.0(3) . . ?
F6 C6 C1 120.5(3) . . ?
C5 C6 C1 122.5(3) . . ?
C8 C7 S1 106.4(2) . . ?
C13 C8 C9 118.7(3) . . ?
C13 C8 C7 121.4(3) . . ?
C9 C8 C7 119.9(3) . . ?
C10 C9 C8 121.5(3) . . ?
C9 C10 C11 118.2(3) . . ?
C12 C11 C10 122.2(3) . . ?
C12 C11 N1 119.2(3) . . ?
C10 C11 N1 118.6(3) . . ?
C11 C12 C13 118.5(3) . . ?
C8 C13 C12 120.9(3) . . ?
O1 N1 O2 123.8(3) . . ?
O1 N1 C11 118.4(3) . . ?
O2 N1 C11 117.8(3) . . ?
C1 S1 C7 103.04(16) . . ?

_refine_diff_density_max         0.299
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_compound2
_database_code_depnum_ccdc_archive 'CCDC 1583011'
loop_
_audit_author_name
_audit_author_address
'Angel Alvarez-Larena' 'Universidad Aut?noma de Barcelona'
_audit_update_record             
;
2017-10-30 deposited with the CCDC.	2019-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
;
4-nitrophenyl 2,3,4,5,6-pentafluorobenzyl sulfide
;
_chemical_formula_moiety         'C13 H6 F5 N O2 S'
_chemical_formula_sum            'C13 H6 F5 N O2 S'
_chemical_formula_weight         335.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.5057(3)
_cell_length_b                   14.4111(9)
_cell_length_c                   16.1789(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1283.69(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4078
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      23.13

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.735
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.320
_shelx_estimated_absorpt_T_min   0.841
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.912
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'SADABS, 2.05'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker SMART-APEX diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.13
_diffrn_reflns_number            10280
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.892
_diffrn_reflns_theta_max         28.787
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3114
_reflns_number_gt                2615
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_max     0.952
_reflns_Friedel_fraction_full    1.000

_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       'SMART 5.6 (Bruker)'
_computing_cell_refinement       'SAINT 5.0 (Bruker)'
_computing_data_reduction        'SAINT 5.0 (Bruker)'
_computing_structure_solution    'SHELXTL-NT 6.1 (Bruker)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0443P)²+0.1152P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.42(11)
_chemical_absolute_configuration .
_refine_ls_number_reflns         3114
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0833
_refine_ls_wR_factor_gt          0.0785
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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
C1 C -0.0940(5) 0.73177(16) 0.29836(14) 0.0428(5) Uani 1 1 d . . . . .
C2 C 0.0935(5) 0.79569(16) 0.29502(15) 0.0439(5) Uani 1 1 d . . . . .
C3 C 0.1186(5) 0.86605(16) 0.35149(16) 0.0473(6) Uani 1 1 d . . . . .
C4 C -0.0479(5) 0.87515(18) 0.41431(17) 0.0499(6) Uani 1 1 d . . . . .
C5 C -0.2375(5) 0.81454(18) 0.41936(17) 0.0498(6) Uani 1 1 d . . . . .
C6 C -0.2593(5) 0.74398(17) 0.36195(16) 0.0461(6) Uani 1 1 d . . . . .
C7 C -0.1193(5) 0.65607(17) 0.23492(16) 0.0523(6) Uani 1 1 d . . . . .
H7A H -0.139636 0.684674 0.181096 0.063 Uiso 1 1 calc R U . . .
H7B H -0.266263 0.621451 0.246788 0.063 Uiso 1 1 calc R U . . .
S1 S 0.13175(15) 0.57500(4) 0.22905(4) 0.05509(19) Uani 1 1 d . . . . .
C8 C 0.1144(5) 0.50622(16) 0.31859(14) 0.0438(5) Uani 1 1 d . . . . .
C9 C -0.0670(5) 0.50977(18) 0.37771(17) 0.0515(6) Uani 1 1 d . . . . .
H9 H -0.198362 0.549566 0.370639 0.062 Uiso 1 1 calc R U . . .
C10 C -0.0535(5) 0.45443(19) 0.44707(17) 0.0521(6) Uani 1 1 d . . . . .
H10 H -0.175142 0.456953 0.486890 0.063 Uiso 1 1 calc R U . . .
C11 C 0.1392(5) 0.39593(16) 0.45701(14) 0.0456(6) Uani 1 1 d . . . . .
C12 C 0.3188(5) 0.38880(18) 0.39826(17) 0.0522(6) Uani 1 1 d . . . . .
H12 H 0.446852 0.347442 0.405182 0.063 Uiso 1 1 calc R U . . .
C13 C 0.3053(5) 0.44393(18) 0.32919(17) 0.0519(6) Uani 1 1 d . . . . .
H13 H 0.425304 0.439614 0.288921 0.062 Uiso 1 1 calc R U . . .
F2 F 0.2567(3) 0.79065(11) 0.23376(10) 0.0630(4) Uani 1 1 d . . . . .
F3 F 0.3058(3) 0.92580(11) 0.34596(11) 0.0657(5) Uani 1 1 d . . . . .
F4 F -0.0247(4) 0.94330(13) 0.46943(11) 0.0744(5) Uani 1 1 d . . . . .
F5 F -0.4020(4) 0.82262(13) 0.47980(12) 0.0742(5) Uani 1 1 d . . . . .
F6 F -0.4506(3) 0.68668(11) 0.36999(12) 0.0637(5) Uani 1 1 d . . . . .
N1 N 0.1592(5) 0.34263(16) 0.53368(13) 0.0575(6) Uani 1 1 d . . . . .
O1 O 0.3433(6) 0.29871(18) 0.54630(14) 0.0893(8) Uani 1 1 d . . . . .
O2 O -0.0108(5) 0.34538(18) 0.58207(13) 0.0780(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.385(4) . ?
C1 C2 1.385(3) . ?
C1 C7 1.504(3) . ?
C2 F2 1.340(3) . ?
C2 C3 1.372(3) . ?
C3 F3 1.346(3) . ?
C3 C4 1.375(4) . ?
C4 F4 1.333(3) . ?
C4 C5 1.363(4) . ?
C5 F5 1.338(3) . ?
C5 C6 1.382(4) . ?
C6 F6 1.345(3) . ?
C7 S1 1.812(3) . ?
S1 C8 1.758(2) . ?
C8 C9 1.384(3) . ?
C8 C13 1.393(4) . ?
C9 C10 1.379(4) . ?
C10 C11 1.365(4) . ?
C11 C12 1.375(4) . ?
C11 N1 1.463(3) . ?
C12 C13 1.373(4) . ?
N1 O1 1.212(4) . ?
N1 O2 1.221(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 C1 C2 115.7(2) . . ?
C6 C1 C7 122.6(2) . . ?
C2 C1 C7 121.6(2) . . ?
F2 C2 C3 117.7(2) . . ?
F2 C2 C1 119.5(2) . . ?
C3 C2 C1 122.7(2) . . ?
F3 C3 C2 120.4(2) . . ?
F3 C3 C4 119.9(2) . . ?
C2 C3 C4 119.7(2) . . ?
F4 C4 C5 120.3(2) . . ?
F4 C4 C3 120.1(3) . . ?
C5 C4 C3 119.6(2) . . ?
F5 C5 C4 120.4(2) . . ?
F5 C5 C6 119.7(2) . . ?
C4 C5 C6 119.8(2) . . ?
F6 C6 C5 117.0(2) . . ?
F6 C6 C1 120.6(2) . . ?
C5 C6 C1 122.4(2) . . ?
C1 C7 S1 115.65(18) . . ?
C8 S1 C7 106.19(13) . . ?
C9 C8 C13 118.9(2) . . ?
C9 C8 S1 126.0(2) . . ?
C13 C8 S1 115.08(19) . . ?
C10 C9 C8 120.1(2) . . ?
C11 C10 C9 119.7(2) . . ?
C10 C11 C12 121.6(2) . . ?
C10 C11 N1 118.9(2) . . ?
C12 C11 N1 119.5(2) . . ?
C13 C12 C11 118.7(2) . . ?
C12 C13 C8 120.9(2) . . ?
O1 N1 O2 123.3(2) . . ?
O1 N1 C11 118.7(3) . . ?
O2 N1 C11 118.0(3) . . ?

_refine_diff_density_max         0.180
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.033

