# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2010


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Peng Li'
_publ_contact_author_email       paullee@sioc.ac.cn
_publ_author_name                'Peng Li'

data_cd29297
_database_code_depnum_ccdc_archive 'CCDC 790386'
#TrackingRef '001.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H20 F5 N O2 S'
_chemical_formula_weight         445.44

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'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   P4(3)2(1)2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   9.7065(7)
_cell_length_b                   9.7065(7)
_cell_length_c                   45.227(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4261.1(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1315
_cell_measurement_theta_min      4.567
_cell_measurement_theta_max      38.072

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.267
_exptl_crystal_size_mid          0.213
_exptl_crystal_size_min          0.075
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1840
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.79563
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22545
_diffrn_reflns_av_R_equivalents  0.1235
_diffrn_reflns_av_sigmaI/netI    0.1311
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -54
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3973
_reflns_number_gt                1455
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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
[0.00000+1.00000exp(3.00(sin\q/\l)^2^)]/
[\s^2^(Fo^2^)+0.0000+0.0000*P+(0.0138P)^2^+0.0000sin\q/\l]
where P = 0.33333Fo^2^ + 0.66667Fc^2^
;
_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_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.55(14)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3973
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1385
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.0781
_refine_ls_wR_factor_gt          0.0580
_refine_ls_goodness_of_fit_ref   0.874
_refine_ls_restrained_S_all      0.874
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.37070(13) 0.86670(12) 1.04413(2) 0.0719(3) Uani 1 1 d . . .
N1 N 0.3822(4) 0.9221(4) 1.00915(6) 0.0657(10) Uani 1 1 d . . .
O1 O 0.2526(4) 0.8807(3) 0.96584(6) 0.0844(9) Uani 1 1 d . . .
O2 O 0.2485(3) 0.7779(3) 1.04612(6) 0.0897(10) Uani 1 1 d . . .
F1 F 0.3132(3) 1.1741(3) 1.03500(6) 0.1211(11) Uani 1 1 d . . .
F2 F 0.5216(3) 1.1424(3) 1.04784(5) 0.1183(11) Uani 1 1 d . . .
F3 F 0.4750(3) 1.2809(3) 1.01329(5) 0.1086(9) Uani 1 1 d . . .
F4 F 0.6283(3) 0.8051(3) 1.03501(5) 0.0992(9) Uani 1 1 d . . .
F5 F 0.4893(3) 0.6327(3) 1.02852(5) 0.1020(9) Uani 1 1 d . . .
C1 C 0.3573(5) 0.8285(4) 0.98414(8) 0.0749(13) Uani 1 1 d . . .
H1 H 0.3318 0.7369 0.9914 0.090 Uiso 1 1 calc R . .
C2 C 0.4853(5) 0.8189(4) 0.96509(9) 0.0864(16) Uani 1 1 d . . .
H2A H 0.4673 0.7579 0.9485 0.104 Uiso 1 1 calc R . .
H2B H 0.5596 0.7793 0.9766 0.104 Uiso 1 1 calc R . .
C3 C 0.5302(4) 0.9596(5) 0.95334(8) 0.0771(13) Uani 1 1 d . . .
H3 H 0.6291 0.9523 0.9493 0.093 Uiso 1 1 calc R . .
C4 C 0.5152(4) 1.0658(4) 0.97683(8) 0.0697(13) Uani 1 1 d . . .
H4 H 0.5533 1.1521 0.9733 0.084 Uiso 1 1 calc R . .
C5 C 0.4517(4) 1.0471(5) 1.00243(9) 0.0641(12) Uani 1 1 d . . .
C6 C 0.4387(7) 1.1579(6) 1.02458(11) 0.0913(17) Uani 1 1 d . . .
C7 C 0.5176(5) 0.7390(5) 1.04648(10) 0.0771(13) Uani 1 1 d . . .
C8 C 0.5406(5) 0.6957(5) 1.07755(9) 0.0685(13) Uani 1 1 d . . .
C9 C 0.6216(5) 0.7756(5) 1.09533(10) 0.0900(15) Uani 1 1 d . . .
H9 H 0.6642 0.8538 1.0877 0.108 Uiso 1 1 calc R . .
C10 C 0.6402(6) 0.7397(6) 1.12465(11) 0.1035(18) Uani 1 1 d . . .
H10 H 0.6950 0.7942 1.1368 0.124 Uiso 1 1 calc R . .
C11 C 0.5797(6) 0.6271(7) 1.13558(11) 0.106(2) Uani 1 1 d . . .
H11 H 0.5935 0.6037 1.1553 0.127 Uiso 1 1 calc R . .
C12 C 0.4981(6) 0.5456(6) 1.11833(12) 0.109(2) Uani 1 1 d . . .
H12 H 0.4567 0.4675 1.1263 0.131 Uiso 1 1 calc R . .
C13 C 0.4772(5) 0.5801(5) 1.08882(11) 0.0973(17) Uani 1 1 d . . .
H13 H 0.4213 0.5259 1.0769 0.117 Uiso 1 1 calc R . .
C14 C 0.4626(5) 1.0013(5) 0.92443(8) 0.0670(12) Uani 1 1 d . . .
C15 C 0.4874(5) 0.9252(5) 0.89920(9) 0.0916(16) Uani 1 1 d . . .
H15 H 0.5442 0.8482 0.9000 0.110 Uiso 1 1 calc R . .
C16 C 0.4271(6) 0.9641(6) 0.87255(11) 0.0998(19) Uani 1 1 d . . .
H16 H 0.4456 0.9126 0.8557 0.120 Uiso 1 1 calc R . .
C17 C 0.3436(6) 1.0731(7) 0.87045(11) 0.107(2) Uani 1 1 d . . .
H17 H 0.3035 1.0967 0.8525 0.129 Uiso 1 1 calc R . .
C18 C 0.3184(5) 1.1485(6) 0.89510(10) 0.1093(19) Uani 1 1 d . . .
H18 H 0.2611 1.2252 0.8941 0.131 Uiso 1 1 calc R . .
C19 C 0.3778(5) 1.1117(5) 0.92197(9) 0.0930(15) Uani 1 1 d . . .
H19 H 0.3589 1.1642 0.9387 0.112 Uiso 1 1 calc R . .
C20 C 0.1201(6) 0.8778(5) 0.97795(9) 0.1053(17) Uani 1 1 d . . .
H20A H 0.1152 0.9402 0.9947 0.126 Uiso 1 1 calc R . .
H20B H 0.0990 0.7856 0.9849 0.126 Uiso 1 1 calc R . .
C21 C 0.0178(5) 0.9201(5) 0.95499(9) 0.132(2) Uani 1 1 d . . .
H21A H 0.0341 1.0142 0.9495 0.198 Uiso 1 1 calc R . .
H21B H -0.0737 0.9114 0.9628 0.198 Uiso 1 1 calc R . .
H21C H 0.0273 0.8620 0.9379 0.198 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0840(9) 0.0833(9) 0.0483(5) 0.0056(7) 0.0009(7) 0.0160(8)
N1 0.087(3) 0.067(3) 0.0440(18) 0.0061(18) -0.002(2) 0.007(2)
O1 0.102(3) 0.097(2) 0.0550(18) 0.0057(19) -0.014(2) 0.009(2)
O2 0.088(2) 0.108(3) 0.0732(19) 0.017(2) 0.0084(19) -0.001(2)
F1 0.128(3) 0.105(3) 0.131(2) -0.031(2) 0.048(2) 0.013(2)
F2 0.174(3) 0.123(2) 0.0583(15) -0.0087(17) -0.0269(18) -0.001(2)
F3 0.158(3) 0.073(2) 0.0940(19) -0.0067(16) 0.0013(19) 0.003(2)
F4 0.0914(19) 0.129(2) 0.0773(16) 0.0313(16) 0.0149(17) 0.0136(19)
F5 0.135(2) 0.100(2) 0.0706(16) -0.0083(17) -0.0160(17) 0.038(2)
C1 0.103(4) 0.059(3) 0.062(3) 0.001(2) -0.016(3) 0.008(3)
C2 0.119(4) 0.081(4) 0.059(3) -0.012(3) -0.006(3) 0.034(3)
C3 0.075(4) 0.098(4) 0.058(3) -0.004(3) -0.002(3) 0.014(3)
C4 0.076(3) 0.080(3) 0.053(3) 0.000(3) -0.009(3) -0.003(3)
C5 0.078(4) 0.068(3) 0.047(2) -0.001(3) -0.013(2) 0.005(3)
C6 0.136(5) 0.078(4) 0.059(3) 0.010(3) -0.006(3) 0.001(4)
C7 0.088(4) 0.082(4) 0.061(3) 0.010(3) 0.003(3) 0.011(3)
C8 0.076(4) 0.075(4) 0.055(3) 0.014(3) 0.005(3) 0.014(3)
C9 0.111(4) 0.088(4) 0.072(3) 0.015(3) 0.009(4) 0.006(4)
C10 0.119(5) 0.125(5) 0.066(4) 0.006(3) -0.017(4) 0.019(4)
C11 0.115(6) 0.146(6) 0.057(3) 0.026(4) 0.005(3) 0.028(5)
C12 0.119(5) 0.122(5) 0.086(5) 0.047(4) -0.003(4) -0.005(4)
C13 0.096(4) 0.105(4) 0.091(4) 0.028(3) -0.009(3) -0.002(3)
C14 0.075(3) 0.082(4) 0.044(2) -0.005(3) 0.009(2) 0.009(3)
C15 0.109(4) 0.107(4) 0.060(3) -0.007(3) 0.011(3) 0.003(3)
C16 0.113(5) 0.137(6) 0.050(3) -0.014(4) 0.010(3) -0.024(4)
C17 0.107(5) 0.158(7) 0.056(3) 0.009(4) -0.012(3) -0.013(4)
C18 0.133(5) 0.127(5) 0.068(3) 0.008(4) -0.007(4) 0.029(4)
C19 0.115(4) 0.108(4) 0.056(3) 0.002(3) -0.001(3) 0.018(4)
C20 0.103(4) 0.119(4) 0.095(4) 0.011(3) -0.009(4) 0.018(4)
C21 0.130(5) 0.147(6) 0.120(4) 0.007(4) -0.066(4) 0.008(4)

_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
S1 O2 1.469(3) . ?
S1 N1 1.675(3) . ?
S1 C7 1.892(5) . ?
N1 C5 1.421(5) . ?
N1 C1 1.471(4) . ?
O1 C20 1.398(5) . ?
O1 C1 1.405(4) . ?
F1 C6 1.316(6) . ?
F2 C6 1.333(5) . ?
F3 C6 1.346(5) . ?
F4 C7 1.355(5) . ?
F5 C7 1.341(5) . ?
C1 C2 1.515(5) . ?
C1 H1 0.9800 . ?
C2 C3 1.529(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.488(5) . ?
C3 C14 1.518(5) . ?
C3 H3 0.9800 . ?
C4 C5 1.324(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.475(6) . ?
C7 C8 1.484(5) . ?
C8 C9 1.367(5) . ?
C8 C13 1.377(5) . ?
C9 C10 1.383(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.336(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.364(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.391(5) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C19 1.355(5) . ?
C14 C15 1.381(5) . ?
C15 C16 1.392(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.337(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.356(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.392(5) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.494(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 N1 107.47(18) . . ?
O2 S1 C7 102.8(2) . . ?
N1 S1 C7 102.29(18) . . ?
C5 N1 C1 116.2(3) . . ?
C5 N1 S1 120.5(3) . . ?
C1 N1 S1 121.1(3) . . ?
C20 O1 C1 115.3(3) . . ?
O1 C1 N1 110.4(3) . . ?
O1 C1 C2 106.3(3) . . ?
N1 C1 C2 109.9(4) . . ?
O1 C1 H1 110.1 . . ?
N1 C1 H1 110.1 . . ?
C2 C1 H1 110.1 . . ?
C1 C2 C3 112.1(3) . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C4 C3 C14 112.8(4) . . ?
C4 C3 C2 110.1(3) . . ?
C14 C3 C2 114.5(4) . . ?
C4 C3 H3 106.3 . . ?
C14 C3 H3 106.3 . . ?
C2 C3 H3 106.3 . . ?
C5 C4 C3 125.1(4) . . ?
C5 C4 H4 117.5 . . ?
C3 C4 H4 117.5 . . ?
C4 C5 N1 121.7(4) . . ?
C4 C5 C6 122.2(5) . . ?
N1 C5 C6 115.9(4) . . ?
F1 C6 F2 106.9(4) . . ?
F1 C6 F3 105.8(5) . . ?
F2 C6 F3 103.9(4) . . ?
F1 C6 C5 114.2(5) . . ?
F2 C6 C5 113.7(5) . . ?
F3 C6 C5 111.5(4) . . ?
F5 C7 F4 107.1(4) . . ?
F5 C7 C8 112.7(4) . . ?
F4 C7 C8 112.2(4) . . ?
F5 C7 S1 108.4(3) . . ?
F4 C7 S1 105.4(3) . . ?
C8 C7 S1 110.6(3) . . ?
C9 C8 C13 120.1(4) . . ?
C9 C8 C7 118.9(5) . . ?
C13 C8 C7 120.9(5) . . ?
C8 C9 C10 119.7(5) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C11 C10 C9 120.2(6) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 121.2(5) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C11 C12 C13 119.6(5) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C8 C13 C12 119.1(5) . . ?
C8 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C19 C14 C15 117.4(4) . . ?
C19 C14 C3 123.0(4) . . ?
C15 C14 C3 119.6(4) . . ?
C14 C15 C16 119.8(5) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C17 C16 C15 122.1(6) . . ?
C17 C16 H16 119.0 . . ?
C15 C16 H16 119.0 . . ?
C16 C17 C18 118.6(6) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 H17 120.7 . . ?
C17 C18 C19 120.3(5) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C14 C19 C18 121.8(4) . . ?
C14 C19 H19 119.1 . . ?
C18 C19 H19 119.1 . . ?
O1 C20 C21 109.5(4) . . ?
O1 C20 H20A 109.8 . . ?
C21 C20 H20A 109.8 . . ?
O1 C20 H20B 109.8 . . ?
C21 C20 H20B 109.8 . . ?
H20A C20 H20B 108.2 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
O2 S1 N1 C5 155.0(3) . . . . ?
C7 S1 N1 C5 -97.2(3) . . . . ?
O2 S1 N1 C1 -42.3(4) . . . . ?
C7 S1 N1 C1 65.4(4) . . . . ?
C20 O1 C1 N1 -70.2(5) . . . . ?
C20 O1 C1 C2 170.6(4) . . . . ?
C5 N1 C1 O1 -73.1(5) . . . . ?
S1 N1 C1 O1 123.5(3) . . . . ?
C5 N1 C1 C2 43.9(5) . . . . ?
S1 N1 C1 C2 -119.5(3) . . . . ?
O1 C1 C2 C3 61.4(4) . . . . ?
N1 C1 C2 C3 -58.2(4) . . . . ?
C1 C2 C3 C4 40.8(5) . . . . ?
C1 C2 C3 C14 -87.5(4) . . . . ?
C14 C3 C4 C5 119.0(5) . . . . ?
C2 C3 C4 C5 -10.2(6) . . . . ?
C3 C4 C5 N1 -4.3(7) . . . . ?
C3 C4 C5 C6 -179.0(4) . . . . ?
C1 N1 C5 C4 -13.5(6) . . . . ?
S1 N1 C5 C4 150.0(3) . . . . ?
C1 N1 C5 C6 161.5(4) . . . . ?
S1 N1 C5 C6 -35.0(5) . . . . ?
C4 C5 C6 F1 131.3(5) . . . . ?
N1 C5 C6 F1 -43.8(6) . . . . ?
C4 C5 C6 F2 -105.7(5) . . . . ?
N1 C5 C6 F2 79.2(6) . . . . ?
C4 C5 C6 F3 11.4(7) . . . . ?
N1 C5 C6 F3 -163.6(4) . . . . ?
O2 S1 C7 F5 45.5(3) . . . . ?
N1 S1 C7 F5 -65.9(4) . . . . ?
O2 S1 C7 F4 159.9(3) . . . . ?
N1 S1 C7 F4 48.6(3) . . . . ?
O2 S1 C7 C8 -78.6(4) . . . . ?
N1 S1 C7 C8 170.0(4) . . . . ?
F5 C7 C8 C9 153.7(4) . . . . ?
F4 C7 C8 C9 32.7(6) . . . . ?
S1 C7 C8 C9 -84.7(5) . . . . ?
F5 C7 C8 C13 -28.9(6) . . . . ?
F4 C7 C8 C13 -149.9(4) . . . . ?
S1 C7 C8 C13 92.7(5) . . . . ?
C13 C8 C9 C10 0.2(7) . . . . ?
C7 C8 C9 C10 177.6(4) . . . . ?
C8 C9 C10 C11 0.3(8) . . . . ?
C9 C10 C11 C12 -0.4(9) . . . . ?
C10 C11 C12 C13 0.0(9) . . . . ?
C9 C8 C13 C12 -0.6(7) . . . . ?
C7 C8 C13 C12 -178.0(4) . . . . ?
C11 C12 C13 C8 0.5(8) . . . . ?
C4 C3 C14 C19 -10.8(7) . . . . ?
C2 C3 C14 C19 116.1(5) . . . . ?
C4 C3 C14 C15 169.0(4) . . . . ?
C2 C3 C14 C15 -64.1(5) . . . . ?
C19 C14 C15 C16 0.6(7) . . . . ?
C3 C14 C15 C16 -179.1(4) . . . . ?
C14 C15 C16 C17 -0.8(9) . . . . ?
C15 C16 C17 C18 0.7(9) . . . . ?
C16 C17 C18 C19 -0.6(9) . . . . ?
C15 C14 C19 C18 -0.5(8) . . . . ?
C3 C14 C19 C18 179.3(5) . . . . ?
C17 C18 C19 C14 0.4(8) . . . . ?
C1 O1 C20 C21 -173.3(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H4 O2 0.93 2.53 3.275(5) 137.4 7_567

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.115
_refine_diff_density_min         -0.111
_refine_diff_density_rms         0.029

# Attachment '002.cif'

data_cd29400
_database_code_depnum_ccdc_archive 'CCDC 790387'
#TrackingRef '002.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 Cl F7 N O2 S'
_chemical_formula_weight         425.75

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   12.1841(15)
_cell_length_b                   5.7816(7)
_cell_length_c                   24.406(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.492(2)
_cell_angle_gamma                90.00
_cell_volume                     1695.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2471
_cell_measurement_theta_min      5.170
_cell_measurement_theta_max      50.418

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.411
_exptl_crystal_size_mid          0.369
_exptl_crystal_size_min          0.223
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    0.430
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.76363
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8450
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_sigmaI/netI    0.0416
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3133
_reflns_number_gt                2317
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.1508P)^2^+0.4758P] where P=(Fo^2^+2Fc^2^)/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_extinction_coef       ?
_refine_ls_number_reflns         3133
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0732
_refine_ls_wR_factor_ref         0.2394
_refine_ls_wR_factor_gt          0.2257
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.002

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.19596(8) 0.05154(17) 0.10981(4) 0.0474(4) Uani 1 1 d . . .
Cl1 Cl 0.16353(16) 0.3050(3) -0.06205(5) 0.1074(7) Uani 1 1 d . . .
F1 F -0.0230(2) 0.2895(7) 0.22699(13) 0.0914(10) Uani 1 1 d . . .
F2 F -0.0142(3) 0.1198(11) 0.15129(18) 0.152(2) Uani 1 1 d . . .
F3 F 0.0099(3) 0.4786(9) 0.15767(18) 0.1378(19) Uani 1 1 d . . .
F4 F 0.0919(3) 0.3602(7) 0.04496(13) 0.1103(13) Uani 1 1 d . . .
F5 F 0.2657(3) 0.4173(6) 0.05811(11) 0.0959(11) Uani 1 1 d . . .
F6 F 0.3020(4) 0.0599(10) -0.00139(19) 0.152(2) Uani 1 1 d . . .
F7 F 0.1365(4) -0.0587(7) -0.00948(14) 0.1257(15) Uani 1 1 d . . .
N1 N 0.2200(2) 0.2542(5) 0.15902(12) 0.0427(7) Uani 1 1 d . . .
O1 O 0.3404(2) 0.5649(5) 0.18947(11) 0.0537(7) Uani 1 1 d . . .
H1 H 0.3127 0.6377 0.1618 0.081 Uiso 1 1 calc R . .
O2 O 0.2964(3) -0.0877(5) 0.10944(12) 0.0623(8) Uani 1 1 d . . .
C1 C 0.3373(3) 0.3289(7) 0.17731(14) 0.0415(8) Uani 1 1 d . . .
H1A H 0.3810 0.2976 0.1478 0.050 Uiso 1 1 calc R . .
C2 C 0.3863(3) 0.1982(7) 0.22949(14) 0.0416(8) Uani 1 1 d . . .
H2A H 0.4642 0.2384 0.2401 0.050 Uiso 1 1 calc R . .
H2B H 0.3814 0.0331 0.2224 0.050 Uiso 1 1 calc R . .
C3 C 0.3226(3) 0.2596(6) 0.27672(14) 0.0412(8) Uani 1 1 d . . .
H3 H 0.3434 0.4182 0.2882 0.049 Uiso 1 1 calc R . .
C4 C 0.1993(3) 0.2607(7) 0.25537(16) 0.0467(9) Uani 1 1 d . . .
H4 H 0.1516 0.2681 0.2814 0.056 Uiso 1 1 calc R . .
C5 C 0.1544(3) 0.2521(7) 0.20280(15) 0.0448(9) Uani 1 1 d . . .
C6 C 0.0324(4) 0.2837(12) 0.1848(2) 0.0778(16) Uani 1 1 d . . .
C7 C 0.3541(3) 0.1084(7) 0.32688(14) 0.0411(8) Uani 1 1 d . . .
C8 C 0.4359(3) 0.1787(8) 0.36942(15) 0.0515(10) Uani 1 1 d . . .
H8 H 0.4704 0.3210 0.3671 0.062 Uiso 1 1 calc R . .
C9 C 0.4676(4) 0.0399(10) 0.41566(17) 0.0667(13) Uani 1 1 d . . .
H9 H 0.5237 0.0880 0.4439 0.080 Uiso 1 1 calc R . .
C10 C 0.4157(4) -0.1687(10) 0.41953(18) 0.0714(14) Uani 1 1 d . . .
H10 H 0.4367 -0.2618 0.4506 0.086 Uiso 1 1 calc R . .
C11 C 0.3340(4) -0.2397(8) 0.37843(19) 0.0657(12) Uani 1 1 d . . .
H11 H 0.2983 -0.3802 0.3815 0.079 Uiso 1 1 calc R . .
C12 C 0.3039(3) -0.1023(7) 0.33176(16) 0.0521(10) Uani 1 1 d . . .
H12 H 0.2489 -0.1533 0.3033 0.063 Uiso 1 1 calc R . .
C13 C 0.1932(4) 0.2544(7) 0.04922(16) 0.0559(11) Uani 1 1 d . . .
C14 C 0.1917(6) 0.1248(12) -0.00441(19) 0.0857(17) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0569(6) 0.0419(6) 0.0408(6) 0.0000(4) 0.0001(4) -0.0046(4)
Cl1 0.1441(15) 0.1295(15) 0.0437(8) 0.0164(7) 0.0007(8) 0.0173(11)
F1 0.0443(14) 0.152(3) 0.080(2) 0.0084(19) 0.0149(13) 0.0211(16)
F2 0.0499(18) 0.260(6) 0.138(4) -0.102(4) -0.0066(19) -0.007(2)
F3 0.081(2) 0.202(5) 0.131(3) 0.095(3) 0.020(2) 0.072(3)
F4 0.119(3) 0.137(3) 0.076(2) 0.029(2) 0.0212(19) 0.077(2)
F5 0.142(3) 0.085(2) 0.0515(16) 0.0167(14) -0.0135(16) -0.055(2)
F6 0.158(4) 0.206(5) 0.106(3) 0.039(3) 0.061(3) 0.104(4)
F7 0.199(4) 0.089(3) 0.078(2) -0.0207(18) -0.009(2) -0.052(3)
N1 0.0418(16) 0.0480(18) 0.0367(16) -0.0005(13) 0.0012(13) 0.0000(13)
O1 0.0699(18) 0.0441(16) 0.0430(15) 0.0062(11) -0.0025(13) -0.0056(13)
O2 0.086(2) 0.0473(16) 0.0516(16) 0.0043(13) 0.0058(15) 0.0213(15)
C1 0.0413(18) 0.047(2) 0.0353(18) 0.0020(15) 0.0030(14) -0.0015(15)
C2 0.0402(18) 0.045(2) 0.0393(19) 0.0036(15) 0.0054(15) 0.0011(15)
C3 0.0441(19) 0.043(2) 0.0354(19) 0.0003(14) 0.0032(15) 0.0030(15)
C4 0.043(2) 0.052(2) 0.046(2) 0.0067(16) 0.0128(17) 0.0114(17)
C5 0.0398(18) 0.056(2) 0.038(2) 0.0037(16) 0.0035(15) 0.0066(16)
C6 0.051(3) 0.122(5) 0.060(3) 0.007(3) 0.005(2) 0.018(3)
C7 0.0435(18) 0.048(2) 0.0313(17) -0.0012(15) 0.0042(14) 0.0054(16)
C8 0.045(2) 0.066(3) 0.041(2) -0.0047(18) -0.0010(16) 0.0031(19)
C9 0.062(3) 0.096(4) 0.037(2) -0.001(2) -0.0042(19) 0.013(3)
C10 0.087(3) 0.085(4) 0.040(2) 0.014(2) 0.005(2) 0.029(3)
C11 0.089(3) 0.051(3) 0.061(3) 0.013(2) 0.023(3) 0.006(2)
C12 0.057(2) 0.055(2) 0.042(2) 0.0022(17) 0.0020(17) 0.0010(19)
C13 0.071(3) 0.051(2) 0.040(2) 0.0029(17) -0.0074(19) 0.001(2)
C14 0.123(5) 0.095(4) 0.038(2) -0.006(2) 0.011(3) -0.014(4)

_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
S1 O2 1.466(3) . ?
S1 N1 1.669(3) . ?
S1 C13 1.884(4) . ?
Cl1 C14 1.739(6) . ?
F1 C6 1.322(6) . ?
F2 C6 1.317(7) . ?
F3 C6 1.312(7) . ?
F4 C13 1.367(5) . ?
F5 C13 1.285(5) . ?
F6 C14 1.386(7) . ?
F7 C14 1.251(7) . ?
N1 C5 1.436(5) . ?
N1 C1 1.489(4) . ?
O1 C1 1.396(5) . ?
O1 H1 0.8200 . ?
C1 C2 1.516(5) . ?
C1 H1A 0.9800 . ?
C2 C3 1.534(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C7 1.502(5) . ?
C3 C4 1.506(5) . ?
C3 H3 0.9800 . ?
C4 C5 1.310(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.491(6) . ?
C7 C8 1.377(5) . ?
C7 C12 1.377(6) . ?
C8 C9 1.386(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.372(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.355(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.388(6) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.506(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
O2 S1 N1 110.03(17) . . ?
O2 S1 C13 104.11(19) . . ?
N1 S1 C13 96.10(17) . . ?
C5 N1 C1 113.8(3) . . ?
C5 N1 S1 118.5(2) . . ?
C1 N1 S1 117.7(2) . . ?
C1 O1 H1 109.5 . . ?
O1 C1 N1 109.8(3) . . ?
O1 C1 C2 108.4(3) . . ?
N1 C1 C2 109.4(3) . . ?
O1 C1 H1A 109.7 . . ?
N1 C1 H1A 109.7 . . ?
C2 C1 H1A 109.7 . . ?
C1 C2 C3 109.7(3) . . ?
C1 C2 H2A 109.7 . . ?
C3 C2 H2A 109.7 . . ?
C1 C2 H2B 109.7 . . ?
C3 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C7 C3 C4 113.0(3) . . ?
C7 C3 C2 112.6(3) . . ?
C4 C3 C2 109.9(3) . . ?
C7 C3 H3 107.0 . . ?
C4 C3 H3 107.0 . . ?
C2 C3 H3 107.0 . . ?
C5 C4 C3 124.8(3) . . ?
C5 C4 H4 117.6 . . ?
C3 C4 H4 117.6 . . ?
C4 C5 N1 122.3(3) . . ?
C4 C5 C6 121.3(4) . . ?
N1 C5 C6 115.5(3) . . ?
F3 C6 F2 105.8(5) . . ?
F3 C6 F1 106.3(5) . . ?
F2 C6 F1 106.2(5) . . ?
F3 C6 C5 111.7(5) . . ?
F2 C6 C5 113.7(5) . . ?
F1 C6 C5 112.7(4) . . ?
C8 C7 C12 118.2(4) . . ?
C8 C7 C3 119.9(4) . . ?
C12 C7 C3 121.9(3) . . ?
C7 C8 C9 120.8(4) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 119.7(4) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C11 C10 C9 120.4(4) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 119.8(5) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C7 C12 C11 121.1(4) . . ?
C7 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
F5 C13 F4 105.8(4) . . ?
F5 C13 C14 114.9(4) . . ?
F4 C13 C14 106.0(4) . . ?
F5 C13 S1 113.7(3) . . ?
F4 C13 S1 103.7(3) . . ?
C14 C13 S1 111.6(4) . . ?
F7 C14 F6 106.1(6) . . ?
F7 C14 C13 115.9(5) . . ?
F6 C14 C13 102.5(4) . . ?
F7 C14 Cl1 113.4(4) . . ?
F6 C14 Cl1 105.4(4) . . ?
C13 C14 Cl1 112.2(4) . . ?

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
O2 S1 N1 C5 -119.3(3) . . . . ?
C13 S1 N1 C5 133.2(3) . . . . ?
O2 S1 N1 C1 24.2(3) . . . . ?
C13 S1 N1 C1 -83.3(3) . . . . ?
C5 N1 C1 O1 -70.5(4) . . . . ?
S1 N1 C1 O1 144.4(2) . . . . ?
C5 N1 C1 C2 48.4(4) . . . . ?
S1 N1 C1 C2 -96.7(3) . . . . ?
O1 C1 C2 C3 56.4(4) . . . . ?
N1 C1 C2 C3 -63.3(4) . . . . ?
C1 C2 C3 C7 170.7(3) . . . . ?
C1 C2 C3 C4 43.7(4) . . . . ?
C7 C3 C4 C5 -138.1(4) . . . . ?
C2 C3 C4 C5 -11.3(5) . . . . ?
C3 C4 C5 N1 -3.8(6) . . . . ?
C3 C4 C5 C6 -172.2(4) . . . . ?
C1 N1 C5 C4 -15.4(5) . . . . ?
S1 N1 C5 C4 129.5(4) . . . . ?
C1 N1 C5 C6 153.7(4) . . . . ?
S1 N1 C5 C6 -61.5(5) . . . . ?
C4 C5 C6 F3 111.2(5) . . . . ?
N1 C5 C6 F3 -57.9(6) . . . . ?
C4 C5 C6 F2 -129.2(5) . . . . ?
N1 C5 C6 F2 61.6(6) . . . . ?
C4 C5 C6 F1 -8.3(7) . . . . ?
N1 C5 C6 F1 -177.5(4) . . . . ?
C4 C3 C7 C8 -141.1(4) . . . . ?
C2 C3 C7 C8 93.6(4) . . . . ?
C4 C3 C7 C12 39.3(5) . . . . ?
C2 C3 C7 C12 -85.9(4) . . . . ?
C12 C7 C8 C9 0.6(6) . . . . ?
C3 C7 C8 C9 -178.9(4) . . . . ?
C7 C8 C9 C10 -1.0(7) . . . . ?
C8 C9 C10 C11 0.1(7) . . . . ?
C9 C10 C11 C12 1.0(7) . . . . ?
C8 C7 C12 C11 0.5(6) . . . . ?
C3 C7 C12 C11 -179.9(4) . . . . ?
C10 C11 C12 C7 -1.3(7) . . . . ?
O2 S1 C13 F5 -74.0(4) . . . . ?
N1 S1 C13 F5 38.5(4) . . . . ?
O2 S1 C13 F4 171.6(3) . . . . ?
N1 S1 C13 F4 -75.9(3) . . . . ?
O2 S1 C13 C14 58.0(4) . . . . ?
N1 S1 C13 C14 170.4(4) . . . . ?
F5 C13 C14 F7 167.8(5) . . . . ?
F4 C13 C14 F7 -75.8(7) . . . . ?
S1 C13 C14 F7 36.5(7) . . . . ?
F5 C13 C14 F6 52.8(6) . . . . ?
F4 C13 C14 F6 169.3(4) . . . . ?
S1 C13 C14 F6 -78.5(5) . . . . ?
F5 C13 C14 Cl1 -59.7(6) . . . . ?
F4 C13 C14 Cl1 56.7(5) . . . . ?
S1 C13 C14 Cl1 168.9(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 S1 0.82 2.96 3.696(3) 150.6 1_565
O1 H1 O2 0.82 2.03 2.791(4) 154.9 1_565

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.928
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.085