# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013


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# 
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#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
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data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 917414'
#TrackingRef '16412_web_deposit_cif_file_0_SeiyaKobatake_1356406736.2c.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H26 F6 S'
_chemical_formula_sum            'C31 H26 F6 S'
_chemical_formula_weight         544.59
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a                   9.6357(10)
_cell_length_b                   11.1807(14)
_cell_length_c                   13.5907(18)
_cell_angle_alpha                96.222(4)
_cell_angle_beta                 107.826(3)
_cell_angle_gamma                108.034(3)
_cell_volume                     1291.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    10280
_cell_measurement_theta_min      3.18
_cell_measurement_theta_max      27.48
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             564
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 10.00
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11484
_diffrn_reflns_av_R_equivalents  0.1154
_diffrn_reflns_av_sigmaI/netI    0.0982
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.18
_diffrn_reflns_theta_max         27.48
_reflns_number_total             5599
_reflns_number_gt                3682
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       PROCESS-AUTO
_computing_cell_refinement       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEP-3
_computing_publication_material  'CrystalStructure 3.6.0'
_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^)+(0.1143P)^2^+3.9653P] 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    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5599
_refine_ls_number_parameters     348
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1325
_refine_ls_R_factor_gt           0.0882
_refine_ls_wR_factor_ref         0.2766
_refine_ls_wR_factor_gt          0.2434
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.76156(15) 0.65590(11) 1.05172(9) 0.0303(3) Uani 1 1 d . . .
F1 F 0.3707(4) 0.5476(3) 0.5394(2) 0.0426(8) Uani 1 1 d . . .
F2 F 0.1635(4) 0.5121(3) 0.5810(2) 0.0418(8) Uani 1 1 d . . .
F3 F 0.2654(4) 0.2976(3) 0.4979(2) 0.0483(9) Uani 1 1 d . . .
F4 F 0.1516(4) 0.2890(3) 0.6141(3) 0.0473(8) Uani 1 1 d . . .
F5 F 0.5350(4) 0.3399(3) 0.6413(3) 0.0492(9) Uani 1 1 d . . .
F6 F 0.3892(4) 0.2429(3) 0.7234(2) 0.0476(9) Uani 1 1 d . . .
C1 C 0.7833(6) 0.9388(5) 0.9848(4) 0.0354(11) Uani 1 1 d . . .
H1A H 0.8426 0.9002 1.0352 0.053 Uiso 1 1 calc R . .
H1B H 0.8048 1.0278 1.0188 0.053 Uiso 1 1 calc R . .
H1C H 0.8145 0.9387 0.9226 0.053 Uiso 1 1 calc R . .
C2 C 0.5509(7) 0.8577(5) 1.0446(4) 0.0374(12) Uani 1 1 d . . .
H2A H 0.4370 0.8140 1.0192 0.056 Uiso 1 1 calc R . .
H2B H 0.5795 0.9465 1.0825 0.056 Uiso 1 1 calc R . .
H2C H 0.6010 0.8115 1.0926 0.056 Uiso 1 1 calc R . .
C3 C 0.6058(6) 0.8594(4) 0.9496(4) 0.0299(10) Uani 1 1 d . . .
H3 H 0.5496 0.9048 0.9018 0.036 Uiso 1 1 calc R . .
C4 C 0.5598(5) 0.7230(4) 0.8851(4) 0.0255(9) Uani 1 1 d . . .
C5 C 0.4481(6) 0.6835(4) 0.7807(4) 0.0274(10) Uani 1 1 d . . .
C6 C 0.3603(6) 0.7623(4) 0.7276(4) 0.0289(10) Uani 1 1 d . . .
H6 H 0.2520 0.7343 0.7169 0.035 Uiso 1 1 calc R . .
C7 C 0.4181(6) 0.8683(4) 0.6934(4) 0.0280(10) Uani 1 1 d . . .
C8 C 0.5878(6) 0.9310(4) 0.7121(4) 0.0285(10) Uani 1 1 d . . .
C9 C 0.6761(6) 0.8619(5) 0.6863(4) 0.0296(10) Uani 1 1 d . . .
H9 H 0.6274 0.7720 0.6552 0.036 Uiso 1 1 calc R . .
C10 C 0.8356(6) 0.9245(5) 0.7062(4) 0.0359(11) Uani 1 1 d . . .
H10 H 0.8942 0.8767 0.6888 0.043 Uiso 1 1 calc R . .
C11 C 0.9080(6) 1.0551(5) 0.7508(4) 0.0346(11) Uani 1 1 d . . .
H11 H 1.0161 1.0973 0.7638 0.042 Uiso 1 1 calc R . .
C12 C 0.8208(6) 1.1250(5) 0.7767(4) 0.0329(11) Uani 1 1 d . . .
H12 H 0.8703 1.2149 0.8075 0.039 Uiso 1 1 calc R . .
C13 C 0.6641(6) 1.0643(5) 0.7579(4) 0.0326(11) Uani 1 1 d . . .
H13 H 0.6067 1.1129 0.7760 0.039 Uiso 1 1 calc R . .
C14 C 0.2855(9) 0.8787(8) 0.5083(5) 0.0588(18) Uani 1 1 d . . .
H14A H 0.3866 0.8906 0.5007 0.088 Uiso 1 1 calc R . .
H14B H 0.2336 0.9275 0.4644 0.088 Uiso 1 1 calc R . .
H14C H 0.2197 0.7868 0.4853 0.088 Uiso 1 1 calc R . .
C15 C 0.1578(7) 0.9033(6) 0.6403(5) 0.0475(14) Uani 1 1 d . . .
H15A H 0.0940 0.8110 0.6154 0.071 Uiso 1 1 calc R . .
H15B H 0.1023 0.9525 0.5998 0.071 Uiso 1 1 calc R . .
H15C H 0.1769 0.9306 0.7157 0.071 Uiso 1 1 calc R . .
C16 C 0.3116(6) 0.9274(5) 0.6247(4) 0.0371(12) Uani 1 1 d . . .
H16 H 0.3688 1.0229 0.6434 0.045 Uiso 1 1 calc R . .
C17 C 0.4114(6) 0.5574(4) 0.7221(4) 0.0288(10) Uani 1 1 d . . .
C18 C 0.3068(6) 0.4981(5) 0.6085(4) 0.0304(10) Uani 1 1 d . . .
C19 C 0.2838(6) 0.3533(5) 0.5963(4) 0.0353(11) Uani 1 1 d . . .
C20 C 0.4283(6) 0.3494(5) 0.6830(4) 0.0348(11) Uani 1 1 d . . .
C21 C 0.4819(5) 0.4734(4) 0.7623(4) 0.0267(9) Uani 1 1 d . . .
C22 C 0.6273(6) 0.6331(5) 0.9251(4) 0.0297(10) Uani 1 1 d . . .
C23 C 0.5929(6) 0.5098(4) 0.8654(4) 0.0276(10) Uani 1 1 d . . .
C24 C 0.6790(6) 0.4388(4) 0.9214(4) 0.0294(10) Uani 1 1 d . . .
H24 H 0.6701 0.3548 0.8912 0.035 Uiso 1 1 calc R . .
C25 C 0.7762(6) 0.5045(4) 1.0235(4) 0.0304(10) Uani 1 1 d . . .
C26 C 0.8825(6) 0.4631(5) 1.1024(4) 0.0306(10) Uani 1 1 d . . .
C27 C 0.9234(6) 0.3577(5) 1.0731(4) 0.0352(11) Uani 1 1 d . . .
H27 H 0.8789 0.3112 1.0013 0.042 Uiso 1 1 calc R . .
C28 C 1.0263(6) 0.3210(5) 1.1465(4) 0.0373(12) Uani 1 1 d . . .
H28 H 1.0488 0.2474 1.1257 0.045 Uiso 1 1 calc R . .
C29 C 1.0982(7) 0.3911(5) 1.2516(4) 0.0401(12) Uani 1 1 d . . .
H29 H 1.1737 0.3685 1.3015 0.048 Uiso 1 1 calc R . .
C30 C 1.0577(7) 0.4943(5) 1.2821(4) 0.0390(12) Uani 1 1 d . . .
H30 H 1.1032 0.5405 1.3540 0.047 Uiso 1 1 calc R . .
C31 C 0.9518(6) 0.5308(5) 1.2087(4) 0.0329(11) Uani 1 1 d . . .
H31 H 0.9261 0.6021 1.2307 0.040 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 0.0360(7) 0.0247(6) 0.0248(6) 0.0033(4) 0.0060(5) 0.0094(5)
F1 0.051(2) 0.0436(18) 0.0280(15) 0.0104(13) 0.0143(13) 0.0096(14)
F2 0.0355(17) 0.0382(17) 0.0395(17) -0.0009(13) 0.0026(13) 0.0111(13)
F3 0.067(2) 0.0438(18) 0.0265(16) -0.0050(13) 0.0067(15) 0.0242(16)
F4 0.0391(19) 0.0350(17) 0.053(2) 0.0048(14) 0.0114(15) 0.0014(13)
F5 0.050(2) 0.052(2) 0.0423(18) -0.0050(15) 0.0147(15) 0.0213(16)
F6 0.070(2) 0.0241(14) 0.0365(17) 0.0059(13) 0.0091(15) 0.0113(14)
C1 0.040(3) 0.026(2) 0.034(3) 0.005(2) 0.011(2) 0.007(2)
C2 0.048(3) 0.034(3) 0.034(3) 0.007(2) 0.018(2) 0.017(2)
C3 0.037(3) 0.023(2) 0.025(2) 0.0048(18) 0.0091(19) 0.0080(19)
C4 0.025(2) 0.024(2) 0.025(2) 0.0032(17) 0.0076(17) 0.0079(17)
C5 0.033(3) 0.023(2) 0.026(2) 0.0059(18) 0.0128(19) 0.0071(18)
C6 0.032(3) 0.028(2) 0.027(2) 0.0068(18) 0.0107(19) 0.0101(19)
C7 0.032(3) 0.025(2) 0.026(2) 0.0039(18) 0.0091(19) 0.0106(18)
C8 0.035(3) 0.023(2) 0.026(2) 0.0042(18) 0.0124(19) 0.0070(18)
C9 0.031(3) 0.026(2) 0.029(2) 0.0041(18) 0.0105(19) 0.0083(18)
C10 0.039(3) 0.031(2) 0.039(3) 0.006(2) 0.018(2) 0.012(2)
C11 0.030(3) 0.034(3) 0.028(2) 0.005(2) 0.007(2) 0.001(2)
C12 0.037(3) 0.024(2) 0.030(2) 0.0009(18) 0.013(2) 0.0017(19)
C13 0.041(3) 0.025(2) 0.030(2) 0.0059(19) 0.014(2) 0.010(2)
C14 0.073(5) 0.083(5) 0.035(3) 0.027(3) 0.019(3) 0.043(4)
C15 0.044(3) 0.055(4) 0.051(4) 0.019(3) 0.017(3) 0.028(3)
C16 0.038(3) 0.031(3) 0.041(3) 0.011(2) 0.011(2) 0.012(2)
C17 0.037(3) 0.026(2) 0.022(2) 0.0070(18) 0.0108(19) 0.0091(19)
C18 0.031(3) 0.031(2) 0.025(2) 0.0048(19) 0.0044(19) 0.0112(19)
C19 0.041(3) 0.031(3) 0.026(2) -0.0017(19) 0.008(2) 0.007(2)
C20 0.045(3) 0.026(2) 0.028(2) 0.0028(19) 0.012(2) 0.009(2)
C21 0.023(2) 0.025(2) 0.024(2) 0.0029(17) 0.0037(17) 0.0047(17)
C22 0.033(3) 0.029(2) 0.023(2) 0.0044(18) 0.0089(19) 0.0065(19)
C23 0.031(3) 0.023(2) 0.024(2) 0.0053(17) 0.0072(18) 0.0070(18)
C24 0.029(3) 0.025(2) 0.030(2) 0.0051(18) 0.0076(19) 0.0064(18)
C25 0.036(3) 0.024(2) 0.027(2) 0.0041(18) 0.011(2) 0.0065(19)
C26 0.033(3) 0.026(2) 0.029(2) 0.0065(19) 0.0094(19) 0.0066(19)
C27 0.043(3) 0.031(2) 0.030(3) 0.006(2) 0.013(2) 0.012(2)
C28 0.035(3) 0.033(3) 0.043(3) 0.011(2) 0.012(2) 0.013(2)
C29 0.041(3) 0.036(3) 0.039(3) 0.015(2) 0.008(2) 0.012(2)
C30 0.040(3) 0.038(3) 0.031(3) 0.007(2) 0.005(2) 0.012(2)
C31 0.040(3) 0.026(2) 0.027(2) 0.0032(18) 0.009(2) 0.008(2)
_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C22 1.743(5) . ?
S1 C25 1.753(5) . ?
F1 C18 1.349(6) . ?
F2 C18 1.379(6) . ?
F3 C19 1.347(6) . ?
F4 C19 1.363(6) . ?
F5 C20 1.342(6) . ?
F6 C20 1.361(6) . ?
C1 C3 1.553(7) . ?
C2 C3 1.537(7) . ?
C3 C4 1.531(6) . ?
C4 C5 1.415(6) . ?
C4 C22 1.427(7) . ?
C5 C17 1.422(6) . ?
C5 C6 1.496(6) . ?
C6 C7 1.341(6) . ?
C7 C8 1.492(7) . ?
C7 C16 1.526(7) . ?
C8 C9 1.405(7) . ?
C8 C13 1.411(6) . ?
C9 C10 1.401(7) . ?
C10 C11 1.380(7) . ?
C11 C12 1.404(8) . ?
C12 C13 1.377(7) . ?
C14 C16 1.533(8) . ?
C15 C16 1.508(8) . ?
C17 C21 1.385(6) . ?
C17 C18 1.500(6) . ?
C18 C19 1.547(7) . ?
C19 C20 1.541(7) . ?
C20 C21 1.498(7) . ?
C21 C23 1.401(6) . ?
C22 C23 1.406(7) . ?
C23 C24 1.432(7) . ?
C24 C25 1.378(7) . ?
C25 C26 1.463(7) . ?
C26 C31 1.402(7) . ?
C26 C27 1.409(7) . ?
C27 C28 1.372(7) . ?
C28 C29 1.396(8) . ?
C29 C30 1.389(8) . ?
C30 C31 1.387(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
C22 S1 C25 93.0(2) . . ?
C4 C3 C2 111.9(4) . . ?
C4 C3 C1 112.6(4) . . ?
C2 C3 C1 111.4(4) . . ?
C5 C4 C22 117.7(4) . . ?
C5 C4 C3 119.5(4) . . ?
C22 C4 C3 122.7(4) . . ?
C4 C5 C17 118.0(4) . . ?
C4 C5 C6 125.2(4) . . ?
C17 C5 C6 116.8(4) . . ?
C7 C6 C5 126.9(4) . . ?
C6 C7 C8 123.1(4) . . ?
C6 C7 C16 121.7(4) . . ?
C8 C7 C16 115.0(4) . . ?
C9 C8 C13 118.2(5) . . ?
C9 C8 C7 122.5(4) . . ?
C13 C8 C7 119.4(4) . . ?
C10 C9 C8 120.5(4) . . ?
C11 C10 C9 120.5(5) . . ?
C10 C11 C12 119.5(5) . . ?
C13 C12 C11 120.5(4) . . ?
C12 C13 C8 120.9(5) . . ?
C15 C16 C7 114.8(4) . . ?
C15 C16 C14 110.8(5) . . ?
C7 C16 C14 108.6(5) . . ?
C21 C17 C5 122.9(4) . . ?
C21 C17 C18 109.3(4) . . ?
C5 C17 C18 127.6(4) . . ?
F1 C18 F2 105.4(4) . . ?
F1 C18 C17 112.9(4) . . ?
F2 C18 C17 114.6(4) . . ?
F1 C18 C19 110.1(4) . . ?
F2 C18 C19 109.9(4) . . ?
C17 C18 C19 104.1(4) . . ?
F3 C19 F4 106.9(4) . . ?
F3 C19 C20 113.3(4) . . ?
F4 C19 C20 109.9(4) . . ?
F3 C19 C18 112.3(4) . . ?
F4 C19 C18 109.3(4) . . ?
C20 C19 C18 105.0(4) . . ?
F5 C20 F6 106.2(4) . . ?
F5 C20 C21 113.6(4) . . ?
F6 C20 C21 113.3(4) . . ?
F5 C20 C19 110.1(4) . . ?
F6 C20 C19 110.6(4) . . ?
C21 C20 C19 103.0(4) . . ?
C17 C21 C23 120.5(4) . . ?
C17 C21 C20 112.3(4) . . ?
C23 C21 C20 127.2(4) . . ?
C23 C22 C4 123.7(4) . . ?
C23 C22 S1 109.6(4) . . ?
C4 C22 S1 126.7(4) . . ?
C21 C23 C22 117.2(4) . . ?
C21 C23 C24 129.3(4) . . ?
C22 C23 C24 113.5(4) . . ?
C25 C24 C23 113.3(4) . . ?
C24 C25 C26 128.3(5) . . ?
C24 C25 S1 110.6(4) . . ?
C26 C25 S1 121.1(4) . . ?
C31 C26 C27 118.0(5) . . ?
C31 C26 C25 120.8(5) . . ?
C27 C26 C25 121.1(5) . . ?
C28 C27 C26 121.1(5) . . ?
C27 C28 C29 120.5(5) . . ?
C30 C29 C28 119.1(5) . . ?
C31 C30 C29 120.8(5) . . ?
C30 C31 C26 120.5(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
C2 C3 C4 C5 112.7(5) . . . . ?
C1 C3 C4 C5 -120.9(5) . . . . ?
C2 C3 C4 C22 -68.4(6) . . . . ?
C1 C3 C4 C22 57.9(6) . . . . ?
C22 C4 C5 C17 -0.5(7) . . . . ?
C3 C4 C5 C17 178.3(4) . . . . ?
C22 C4 C5 C6 177.1(4) . . . . ?
C3 C4 C5 C6 -4.0(7) . . . . ?
C4 C5 C6 C7 71.1(7) . . . . ?
C17 C5 C6 C7 -111.2(6) . . . . ?
C5 C6 C7 C8 -5.2(8) . . . . ?
C5 C6 C7 C16 169.9(5) . . . . ?
C6 C7 C8 C9 51.8(7) . . . . ?
C16 C7 C8 C9 -123.7(5) . . . . ?
C6 C7 C8 C13 -127.8(5) . . . . ?
C16 C7 C8 C13 56.7(6) . . . . ?
C13 C8 C9 C10 0.2(7) . . . . ?
C7 C8 C9 C10 -179.4(4) . . . . ?
C8 C9 C10 C11 -0.4(8) . . . . ?
C9 C10 C11 C12 0.3(8) . . . . ?
C10 C11 C12 C13 -0.1(8) . . . . ?
C11 C12 C13 C8 -0.1(7) . . . . ?
C9 C8 C13 C12 0.0(7) . . . . ?
C7 C8 C13 C12 179.6(4) . . . . ?
C6 C7 C16 C15 27.6(7) . . . . ?
C8 C7 C16 C15 -156.9(5) . . . . ?
C6 C7 C16 C14 -97.0(6) . . . . ?
C8 C7 C16 C14 78.5(6) . . . . ?
C4 C5 C17 C21 -1.1(7) . . . . ?
C6 C5 C17 C21 -178.9(4) . . . . ?
C4 C5 C17 C18 -175.1(5) . . . . ?
C6 C5 C17 C18 7.1(7) . . . . ?
C21 C17 C18 F1 -102.4(5) . . . . ?
C5 C17 C18 F1 72.4(6) . . . . ?
C21 C17 C18 F2 137.0(4) . . . . ?
C5 C17 C18 F2 -48.3(7) . . . . ?
C21 C17 C18 C19 17.0(5) . . . . ?
C5 C17 C18 C19 -168.3(5) . . . . ?
F1 C18 C19 F3 -27.0(6) . . . . ?
F2 C18 C19 F3 88.6(5) . . . . ?
C17 C18 C19 F3 -148.3(4) . . . . ?
F1 C18 C19 F4 -145.6(4) . . . . ?
F2 C18 C19 F4 -29.9(5) . . . . ?
C17 C18 C19 F4 93.2(5) . . . . ?
F1 C18 C19 C20 96.6(4) . . . . ?
F2 C18 C19 C20 -147.8(4) . . . . ?
C17 C18 C19 C20 -24.7(5) . . . . ?
F3 C19 C20 F5 24.6(6) . . . . ?
F4 C19 C20 F5 144.1(4) . . . . ?
C18 C19 C20 F5 -98.4(5) . . . . ?
F3 C19 C20 F6 -92.5(5) . . . . ?
F4 C19 C20 F6 27.0(6) . . . . ?
C18 C19 C20 F6 144.5(4) . . . . ?
F3 C19 C20 C21 146.1(4) . . . . ?
F4 C19 C20 C21 -94.4(4) . . . . ?
C18 C19 C20 C21 23.1(5) . . . . ?
C5 C17 C21 C23 1.0(7) . . . . ?
C18 C17 C21 C23 176.1(4) . . . . ?
C5 C17 C21 C20 -177.2(4) . . . . ?
C18 C17 C21 C20 -2.2(6) . . . . ?
F5 C20 C21 C17 105.5(5) . . . . ?
F6 C20 C21 C17 -133.1(5) . . . . ?
C19 C20 C21 C17 -13.5(5) . . . . ?
F5 C20 C21 C23 -72.6(6) . . . . ?
F6 C20 C21 C23 48.8(7) . . . . ?
C19 C20 C21 C23 168.3(5) . . . . ?
C5 C4 C22 C23 2.2(7) . . . . ?
C3 C4 C22 C23 -176.6(5) . . . . ?
C5 C4 C22 S1 -177.7(4) . . . . ?
C3 C4 C22 S1 3.5(7) . . . . ?
C25 S1 C22 C23 1.8(4) . . . . ?
C25 S1 C22 C4 -178.2(5) . . . . ?
C17 C21 C23 C22 0.6(7) . . . . ?
C20 C21 C23 C22 178.6(5) . . . . ?
C17 C21 C23 C24 -179.7(5) . . . . ?
C20 C21 C23 C24 -1.7(9) . . . . ?
C4 C22 C23 C21 -2.2(7) . . . . ?
S1 C22 C23 C21 177.7(4) . . . . ?
C4 C22 C23 C24 178.0(5) . . . . ?
S1 C22 C23 C24 -2.1(5) . . . . ?
C21 C23 C24 C25 -178.5(5) . . . . ?
C22 C23 C24 C25 1.3(6) . . . . ?
C23 C24 C25 C26 -178.8(5) . . . . ?
C23 C24 C25 S1 0.2(5) . . . . ?
C22 S1 C25 C24 -1.2(4) . . . . ?
C22 S1 C25 C26 177.9(4) . . . . ?
C24 C25 C26 C31 -168.1(5) . . . . ?
S1 C25 C26 C31 12.9(7) . . . . ?
C24 C25 C26 C27 14.5(8) . . . . ?
S1 C25 C26 C27 -164.4(4) . . . . ?
C31 C26 C27 C28 0.8(8) . . . . ?
C25 C26 C27 C28 178.2(5) . . . . ?
C26 C27 C28 C29 -2.7(8) . . . . ?
C27 C28 C29 C30 3.4(8) . . . . ?
C28 C29 C30 C31 -2.4(9) . . . . ?
C29 C30 C31 C26 0.6(8) . . . . ?
C27 C26 C31 C30 0.2(7) . . . . ?
C25 C26 C31 C30 -177.2(5) . . . . ?
_diffrn_measured_fraction_theta_max 0.944
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.944
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.102


data_shelxl2
_database_code_depnum_ccdc_archive 'CCDC 917415'
#TrackingRef '16413_web_deposit_cif_file_1_SeiyaKobatake_1356406736.2d.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H20 F6 S '
_chemical_formula_sum            'C28 H20 F6 S '
_chemical_formula_weight         502.51
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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   'P 1 21/c 1'
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                   6.720(3)
_cell_length_b                   21.116(12)
_cell_length_c                   16.274(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.32(4)
_cell_angle_gamma                90.00
_cell_volume                     2299(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    16977
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5
_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1032
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 10.00
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19825
_diffrn_reflns_av_R_equivalents  0.1086
_diffrn_reflns_av_sigmaI/netI    0.0890
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         27.48
_reflns_number_total             5266
_reflns_number_gt                3008
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       PROCESS-AUTO
_computing_cell_refinement       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_structure_solution    SIR92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEP-3
_computing_publication_material  'CrystalStructure 3.6.0'
_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^)+(0.0784P)^2^+0.0000P] 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         5273
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1080
_refine_ls_R_factor_gt           0.0613
_refine_ls_wR_factor_ref         0.1668
_refine_ls_wR_factor_gt          0.1509
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.64325(10) 0.11757(3) 0.43110(5) 0.0342(2) Uani 1 1 d . . .
F1 F 0.1394(3) 0.05130(9) 0.15899(14) 0.0671(7) Uani 1 1 d . . .
F2 F 0.2861(3) 0.13213(11) 0.11134(12) 0.0582(6) Uani 1 1 d . . .
F3 F -0.1949(3) 0.10541(10) 0.14876(14) 0.0606(6) Uani 1 1 d . . .
F4 F -0.0621(3) 0.17050(10) 0.06764(12) 0.0593(6) Uani 1 1 d . . .
F5 F -0.2475(2) 0.20190(9) 0.23529(12) 0.0441(5) Uani 1 1 d . . .
F6 F -0.0307(3) 0.25711(8) 0.17591(12) 0.0495(5) Uani 1 1 d . . .
C1 C 0.4251(4) 0.14808(13) 0.37860(18) 0.0301(6) Uani 1 1 d . . .
C2 C 0.3910(4) 0.11721(13) 0.30183(18) 0.0307(6) Uani 1 1 d . . .
C3 C 0.5369(4) 0.07064(13) 0.28818(19) 0.0324(7) Uani 1 1 d . . .
H3 H 0.5328 0.0461 0.2406 0.039 Uiso 1 1 calc R . .
C4 C 0.6822(4) 0.06545(13) 0.35105(19) 0.0328(7) Uani 1 1 d . . .
C5 C 0.8595(4) 0.02411(14) 0.35815(19) 0.0328(7) Uani 1 1 d . . .
C6 C 0.8586(4) -0.03221(15) 0.3133(2) 0.0398(8) Uani 1 1 d . . .
H6 H 0.7448 -0.0438 0.2798 0.048 Uiso 1 1 calc R . .
C7 C 1.0249(4) -0.07090(15) 0.3181(2) 0.0433(8) Uani 1 1 d . . .
H7 H 1.0230 -0.1083 0.2878 0.052 Uiso 1 1 calc R . .
C8 C 1.1944(4) -0.05405(15) 0.3681(2) 0.0410(8) Uani 1 1 d . . .
H8 H 1.3066 -0.0800 0.3712 0.049 Uiso 1 1 calc R . .
C9 C 1.1971(4) 0.00104(14) 0.4131(2) 0.0369(7) Uani 1 1 d . . .
H9 H 1.3113 0.0123 0.4466 0.044 Uiso 1 1 calc R . .
C10 C 1.0304(4) 0.03983(14) 0.40873(19) 0.0353(7) Uani 1 1 d . . .
H10 H 1.0328 0.0768 0.4399 0.042 Uiso 1 1 calc R . .
C11 C 0.2207(4) 0.13652(13) 0.25077(18) 0.0313(7) Uani 1 1 d . . .
C12 C 0.1569(4) 0.11485(15) 0.16625(19) 0.0373(7) Uani 1 1 d . . .
C13 C -0.0468(4) 0.14761(15) 0.14456(19) 0.0371(7) Uani 1 1 d . . .
C14 C -0.0609(4) 0.19945(14) 0.2102(2) 0.0363(7) Uani 1 1 d . . .
C15 C 0.0998(4) 0.18342(13) 0.27690(18) 0.0307(6) Uani 1 1 d . . .
C16 C 0.3009(4) 0.19498(13) 0.40690(18) 0.0319(7) Uani 1 1 d . . .
C17 C 0.1355(4) 0.21408(13) 0.35337(19) 0.0316(7) Uani 1 1 d . . .
C18 C 0.0008(4) 0.26634(14) 0.37424(19) 0.0363(7) Uani 1 1 d . . .
H18 H -0.1287 0.2552 0.3842 0.044 Uiso 1 1 calc R . .
C19 C 0.0477(4) 0.32749(15) 0.37997(19) 0.0375(7) Uani 1 1 d . . .
H19 H -0.0524 0.3543 0.3952 0.045 Uiso 1 1 calc R . .
C20 C 0.2375(4) 0.35808(14) 0.3653(2) 0.0368(7) Uani 1 1 d . . .
C21 C 0.2899(5) 0.41496(16) 0.4053(2) 0.0456(8) Uani 1 1 d . . .
H21 H 0.2047 0.4325 0.4410 0.055 Uiso 1 1 calc R . .
C22 C 0.4661(5) 0.44568(16) 0.3928(2) 0.0493(9) Uani 1 1 d . . .
H22 H 0.4985 0.4834 0.4205 0.059 Uiso 1 1 calc R . .
C23 C 0.5939(5) 0.42108(15) 0.3399(2) 0.0471(9) Uani 1 1 d . . .
H23 H 0.7127 0.4418 0.3318 0.057 Uiso 1 1 calc R . .
C24 C 0.5443(4) 0.36533(15) 0.2988(2) 0.0418(8) Uani 1 1 d . . .
H24 H 0.6297 0.3485 0.2626 0.050 Uiso 1 1 calc R . .
C25 C 0.3676(4) 0.33418(14) 0.3111(2) 0.0381(7) Uani 1 1 d . . .
H25 H 0.3357 0.2968 0.2828 0.046 Uiso 1 1 calc R . .
C26 C 0.3347(4) 0.22244(14) 0.4934(2) 0.0368(7) Uani 1 1 d . . .
H26 H 0.2343 0.2557 0.4970 0.044 Uiso 1 1 calc R . .
C27 C 0.2939(5) 0.17252(17) 0.5579(2) 0.0464(8) Uani 1 1 d . . .
H27A H 0.1569 0.1592 0.5494 0.070 Uiso 1 1 calc R . .
H27B H 0.3193 0.1903 0.6121 0.070 Uiso 1 1 calc R . .
H27C H 0.3799 0.1367 0.5526 0.070 Uiso 1 1 calc R . .
C28 C 0.5392(4) 0.25390(16) 0.5134(2) 0.0450(8) Uani 1 1 d . . .
H28A H 0.6415 0.2220 0.5175 0.068 Uiso 1 1 calc R . .
H28B H 0.5405 0.2761 0.5649 0.068 Uiso 1 1 calc R . .
H28C H 0.5635 0.2832 0.4704 0.068 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 0.0309(4) 0.0310(4) 0.0392(4) -0.0003(3) -0.0046(3) 0.0043(3)
F1 0.0882(15) 0.0330(11) 0.0717(15) -0.0082(10) -0.0382(12) 0.0054(11)
F2 0.0384(10) 0.0942(16) 0.0417(11) -0.0018(11) 0.0024(9) 0.0083(10)
F3 0.0418(10) 0.0640(14) 0.0766(15) -0.0236(12) 0.0081(10) -0.0164(10)
F4 0.0638(12) 0.0740(14) 0.0392(11) 0.0157(10) 0.0000(10) 0.0269(11)
F5 0.0296(8) 0.0463(11) 0.0554(12) 0.0014(9) -0.0013(8) 0.0048(8)
F6 0.0524(11) 0.0348(10) 0.0581(12) 0.0201(9) -0.0127(9) -0.0029(8)
C1 0.0268(13) 0.0243(14) 0.0384(17) 0.0057(13) -0.0021(12) 0.0005(11)
C2 0.0314(14) 0.0254(14) 0.0346(16) 0.0022(13) -0.0006(12) -0.0009(12)
C3 0.0326(14) 0.0247(14) 0.0394(17) 0.0006(13) 0.0004(13) -0.0008(12)
C4 0.0306(14) 0.0263(14) 0.0413(18) 0.0044(13) 0.0024(13) -0.0004(12)
C5 0.0288(14) 0.0306(15) 0.0387(17) 0.0049(13) 0.0013(13) 0.0019(12)
C6 0.0353(15) 0.0352(17) 0.0475(19) -0.0005(15) -0.0028(14) 0.0050(13)
C7 0.0447(17) 0.0339(17) 0.050(2) -0.0031(15) -0.0024(16) 0.0080(14)
C8 0.0361(16) 0.0386(18) 0.0483(19) 0.0082(15) 0.0034(15) 0.0099(14)
C9 0.0309(14) 0.0357(17) 0.0437(18) 0.0058(15) 0.0004(13) -0.0002(13)
C10 0.0351(15) 0.0259(15) 0.0442(18) 0.0037(14) 0.0001(13) -0.0010(12)
C11 0.0297(14) 0.0257(14) 0.0376(17) 0.0048(13) -0.0018(13) -0.0041(12)
C12 0.0366(16) 0.0342(16) 0.0398(18) 0.0042(14) -0.0039(14) -0.0003(14)
C13 0.0324(15) 0.0436(18) 0.0346(17) 0.0093(14) -0.0010(13) -0.0037(13)
C14 0.0315(15) 0.0318(16) 0.0442(18) 0.0104(14) -0.0033(13) -0.0020(13)
C15 0.0266(13) 0.0283(15) 0.0366(17) 0.0058(13) 0.0008(12) -0.0019(12)
C16 0.0313(14) 0.0269(15) 0.0368(17) 0.0037(13) -0.0009(13) -0.0033(12)
C17 0.0291(14) 0.0241(14) 0.0417(18) 0.0033(13) 0.0036(13) -0.0015(12)
C18 0.0297(14) 0.0389(17) 0.0399(18) 0.0030(15) 0.0007(13) 0.0025(13)
C19 0.0368(15) 0.0372(17) 0.0386(18) 0.0016(14) 0.0035(14) 0.0094(14)
C20 0.0383(16) 0.0284(15) 0.0424(18) 0.0031(14) -0.0024(14) 0.0057(13)
C21 0.0538(19) 0.0399(19) 0.043(2) -0.0011(16) 0.0021(16) 0.0071(16)
C22 0.061(2) 0.0316(17) 0.052(2) -0.0007(16) -0.0112(18) -0.0024(17)
C23 0.0443(17) 0.0333(17) 0.061(2) 0.0057(16) -0.0082(17) -0.0021(15)
C24 0.0372(16) 0.0372(17) 0.051(2) 0.0103(16) 0.0034(15) 0.0018(14)
C25 0.0415(16) 0.0255(15) 0.0464(19) 0.0028(14) -0.0004(15) 0.0011(13)
C26 0.0333(15) 0.0333(16) 0.0433(18) -0.0029(14) 0.0004(14) 0.0050(13)
C27 0.0522(19) 0.053(2) 0.0342(18) 0.0038(16) 0.0040(15) 0.0089(17)
C28 0.0373(16) 0.046(2) 0.051(2) -0.0136(16) -0.0027(15) 0.0016(15)
_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 C4 1.744(3) . ?
S1 C1 1.750(3) . ?
F1 C12 1.351(4) . ?
F2 C12 1.352(4) . ?
F3 C13 1.342(3) . ?
F4 C13 1.337(4) . ?
F5 C14 1.355(3) . ?
F6 C14 1.363(3) . ?
C1 C16 1.400(4) . ?
C1 C2 1.409(4) . ?
C2 C11 1.411(4) . ?
C2 C3 1.420(4) . ?
C3 C4 1.352(4) . ?
C4 C5 1.473(4) . ?
C5 C10 1.390(4) . ?
C5 C6 1.395(4) . ?
C6 C7 1.380(4) . ?
C7 C8 1.383(4) . ?
C8 C9 1.374(4) . ?
C9 C10 1.384(4) . ?
C11 C15 1.373(4) . ?
C11 C12 1.475(4) . ?
C12 C13 1.545(4) . ?
C13 C14 1.539(5) . ?
C14 C15 1.496(4) . ?
C15 C17 1.404(4) . ?
C16 C17 1.406(4) . ?
C16 C26 1.519(4) . ?
C17 C18 1.486(4) . ?
C18 C19 1.330(4) . ?
C19 C20 1.469(4) . ?
C20 C25 1.393(4) . ?
C20 C21 1.396(4) . ?
C21 C22 1.381(5) . ?
C22 C23 1.373(5) . ?
C23 C24 1.380(5) . ?
C24 C25 1.388(4) . ?
C26 C27 1.531(5) . ?
C26 C28 1.534(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
C4 S1 C1 92.56(14) . . ?
C16 C1 C2 124.5(3) . . ?
C16 C1 S1 126.7(2) . . ?
C2 C1 S1 108.8(2) . . ?
C1 C2 C11 116.4(3) . . ?
C1 C2 C3 113.7(2) . . ?
C11 C2 C3 129.9(3) . . ?
C4 C3 C2 113.5(3) . . ?
C3 C4 C5 129.0(3) . . ?
C3 C4 S1 111.5(2) . . ?
C5 C4 S1 119.5(2) . . ?
C10 C5 C6 118.5(3) . . ?
C10 C5 C4 121.5(3) . . ?
C6 C5 C4 120.0(3) . . ?
C7 C6 C5 120.7(3) . . ?
C6 C7 C8 119.9(3) . . ?
C9 C8 C7 120.1(3) . . ?
C8 C9 C10 120.2(3) . . ?
C9 C10 C5 120.6(3) . . ?
C15 C11 C2 119.8(3) . . ?
C15 C11 C12 112.5(3) . . ?
C2 C11 C12 127.5(3) . . ?
F1 C12 F2 105.4(3) . . ?
F1 C12 C11 113.9(3) . . ?
F2 C12 C11 112.6(2) . . ?
F1 C12 C13 110.9(2) . . ?
F2 C12 C13 109.7(2) . . ?
C11 C12 C13 104.4(3) . . ?
F4 C13 F3 107.1(2) . . ?
F4 C13 C14 112.9(3) . . ?
F3 C13 C14 110.1(3) . . ?
F4 C13 C12 111.5(3) . . ?
F3 C13 C12 109.7(2) . . ?
C14 C13 C12 105.7(2) . . ?
F5 C14 F6 105.4(2) . . ?
F5 C14 C15 114.6(3) . . ?
F6 C14 C15 112.0(2) . . ?
F5 C14 C13 110.7(2) . . ?
F6 C14 C13 109.2(3) . . ?
C15 C14 C13 104.8(2) . . ?
C11 C15 C17 123.4(3) . . ?
C11 C15 C14 110.3(3) . . ?
C17 C15 C14 126.2(3) . . ?
C1 C16 C17 117.4(3) . . ?
C1 C16 C26 122.1(2) . . ?
C17 C16 C26 120.4(3) . . ?
C15 C17 C16 118.5(3) . . ?
C15 C17 C18 119.2(2) . . ?
C16 C17 C18 122.3(3) . . ?
C19 C18 C17 126.2(3) . . ?
C18 C19 C20 128.3(3) . . ?
C25 C20 C21 117.4(3) . . ?
C25 C20 C19 123.3(3) . . ?
C21 C20 C19 119.2(3) . . ?
C22 C21 C20 121.2(3) . . ?
C23 C22 C21 120.6(3) . . ?
C22 C23 C24 119.3(3) . . ?
C23 C24 C25 120.4(3) . . ?
C24 C25 C20 121.1(3) . . ?
C16 C26 C27 110.6(3) . . ?
C16 C26 C28 114.6(3) . . ?
C27 C26 C28 111.5(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
C4 S1 C1 C16 179.4(3) . . . . ?
C4 S1 C1 C2 -0.1(2) . . . . ?
C16 C1 C2 C11 1.0(4) . . . . ?
S1 C1 C2 C11 -179.5(2) . . . . ?
C16 C1 C2 C3 -178.9(3) . . . . ?
S1 C1 C2 C3 0.5(3) . . . . ?
C1 C2 C3 C4 -0.9(4) . . . . ?
C11 C2 C3 C4 179.2(3) . . . . ?
C2 C3 C4 C5 -178.2(3) . . . . ?
C2 C3 C4 S1 0.8(3) . . . . ?
C1 S1 C4 C3 -0.4(2) . . . . ?
C1 S1 C4 C5 178.7(2) . . . . ?
C3 C4 C5 C10 154.8(3) . . . . ?
S1 C4 C5 C10 -24.1(4) . . . . ?
C3 C4 C5 C6 -25.0(5) . . . . ?
S1 C4 C5 C6 156.1(2) . . . . ?
C10 C5 C6 C7 -1.0(5) . . . . ?
C4 C5 C6 C7 178.8(3) . . . . ?
C5 C6 C7 C8 0.3(5) . . . . ?
C6 C7 C8 C9 0.2(5) . . . . ?
C7 C8 C9 C10 0.1(5) . . . . ?
C8 C9 C10 C5 -0.8(5) . . . . ?
C6 C5 C10 C9 1.3(4) . . . . ?
C4 C5 C10 C9 -178.5(3) . . . . ?
C1 C2 C11 C15 0.4(4) . . . . ?
C3 C2 C11 C15 -179.6(3) . . . . ?
C1 C2 C11 C12 176.3(3) . . . . ?
C3 C2 C11 C12 -3.8(5) . . . . ?
C15 C11 C12 F1 -129.7(3) . . . . ?
C2 C11 C12 F1 54.3(4) . . . . ?
C15 C11 C12 F2 110.4(3) . . . . ?
C2 C11 C12 F2 -65.7(4) . . . . ?
C15 C11 C12 C13 -8.5(3) . . . . ?
C2 C11 C12 C13 175.4(3) . . . . ?
F1 C12 C13 F4 -99.8(3) . . . . ?
F2 C12 C13 F4 16.2(4) . . . . ?
C11 C12 C13 F4 137.1(3) . . . . ?
F1 C12 C13 F3 18.6(4) . . . . ?
F2 C12 C13 F3 134.7(3) . . . . ?
C11 C12 C13 F3 -104.4(3) . . . . ?
F1 C12 C13 C14 137.2(3) . . . . ?
F2 C12 C13 C14 -106.7(3) . . . . ?
C11 C12 C13 C14 14.1(3) . . . . ?
F4 C13 C14 F5 99.1(3) . . . . ?
F3 C13 C14 F5 -20.5(3) . . . . ?
C12 C13 C14 F5 -138.8(2) . . . . ?
F4 C13 C14 F6 -16.6(3) . . . . ?
F3 C13 C14 F6 -136.2(2) . . . . ?
C12 C13 C14 F6 105.5(3) . . . . ?
F4 C13 C14 C15 -136.8(2) . . . . ?
F3 C13 C14 C15 103.6(3) . . . . ?
C12 C13 C14 C15 -14.7(3) . . . . ?
C2 C11 C15 C17 -0.2(4) . . . . ?
C12 C11 C15 C17 -176.6(3) . . . . ?
C2 C11 C15 C14 175.5(2) . . . . ?
C12 C11 C15 C14 -1.0(3) . . . . ?
F5 C14 C15 C11 131.7(3) . . . . ?
F6 C14 C15 C11 -108.3(3) . . . . ?
C13 C14 C15 C11 10.1(3) . . . . ?
F5 C14 C15 C17 -52.8(4) . . . . ?
F6 C14 C15 C17 67.2(4) . . . . ?
C13 C14 C15 C17 -174.4(3) . . . . ?
C2 C1 C16 C17 -2.6(4) . . . . ?
S1 C1 C16 C17 178.0(2) . . . . ?
C2 C1 C16 C26 174.4(3) . . . . ?
S1 C1 C16 C26 -5.0(4) . . . . ?
C11 C15 C17 C16 -1.5(4) . . . . ?
C14 C15 C17 C16 -176.4(3) . . . . ?
C11 C15 C17 C18 177.2(3) . . . . ?
C14 C15 C17 C18 2.3(4) . . . . ?
C1 C16 C17 C15 2.7(4) . . . . ?
C26 C16 C17 C15 -174.3(3) . . . . ?
C1 C16 C17 C18 -175.9(3) . . . . ?
C26 C16 C17 C18 7.1(4) . . . . ?
C15 C17 C18 C19 -110.1(4) . . . . ?
C16 C17 C18 C19 68.5(4) . . . . ?
C17 C18 C19 C20 1.8(5) . . . . ?
C18 C19 C20 C25 28.3(5) . . . . ?
C18 C19 C20 C21 -153.6(3) . . . . ?
C25 C20 C21 C22 -1.2(5) . . . . ?
C19 C20 C21 C22 -179.5(3) . . . . ?
C20 C21 C22 C23 0.5(5) . . . . ?
C21 C22 C23 C24 0.3(5) . . . . ?
C22 C23 C24 C25 -0.4(5) . . . . ?
C23 C24 C25 C20 -0.3(5) . . . . ?
C21 C20 C25 C24 1.1(4) . . . . ?
C19 C20 C25 C24 179.3(3) . . . . ?
C1 C16 C26 C27 -67.9(3) . . . . ?
C17 C16 C26 C27 109.0(3) . . . . ?
C1 C16 C26 C28 59.1(4) . . . . ?
C17 C16 C26 C28 -124.0(3) . . . . ?
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.065


data_shelxl3
_database_code_depnum_ccdc_archive 'CCDC 917416'
#TrackingRef '16414_web_deposit_cif_file_2_SeiyaKobatake_1356406736.2e.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H26 F6 S'
_chemical_formula_sum            'C31 H26 F6 S'
_chemical_formula_weight         544.59
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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   'C 1 2/c 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a                   38.047(4)
_cell_length_b                   6.0219(6)
_cell_length_c                   23.213(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.266(3)
_cell_angle_gamma                90.00
_cell_volume                     5216.0(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    13990
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.4
_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2256
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 10.00
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20530
_diffrn_reflns_av_R_equivalents  0.1255
_diffrn_reflns_av_sigmaI/netI    0.0996
_diffrn_reflns_limit_h_min       -47
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         27.44
_reflns_number_total             5934
_reflns_number_gt                3552
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       PROCESS-AUTO
_computing_cell_refinement       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEP-3
_computing_publication_material  'CrystalStructure 3.6.0'
_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^)+(0.0767P)^2^+20.8646P] 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    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5934
_refine_ls_number_parameters     348
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1300
_refine_ls_R_factor_gt           0.0786
_refine_ls_wR_factor_ref         0.2251
_refine_ls_wR_factor_gt          0.2012
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.54151(3) 0.8800(2) 0.46400(5) 0.0333(3) Uani 1 1 d . . .
F1 F 0.65558(7) 0.2226(5) 0.31633(11) 0.0422(7) Uani 1 1 d . . .
F2 F 0.63607(7) 0.4962(5) 0.25727(10) 0.0408(7) Uani 1 1 d . . .
F3 F 0.59526(8) 0.0371(5) 0.30091(15) 0.0554(8) Uani 1 1 d . . .
F4 F 0.58334(7) 0.2399(6) 0.22219(11) 0.0525(8) Uani 1 1 d . . .
F5 F 0.54340(7) 0.2306(4) 0.33091(12) 0.0429(7) Uani 1 1 d . . .
F6 F 0.54243(7) 0.4930(5) 0.26592(11) 0.0430(7) Uani 1 1 d . . .
C1 C 0.69850(11) 0.6867(7) 0.51452(19) 0.0321(10) Uani 1 1 d . . .
H1A H 0.6876 0.5420 0.5193 0.048 Uiso 1 1 calc R . .
H1B H 0.7104 0.7428 0.5530 0.048 Uiso 1 1 calc R . .
H1C H 0.7161 0.6707 0.4892 0.048 Uiso 1 1 calc R . .
C2 C 0.68613(12) 1.0621(7) 0.4662(2) 0.0350(10) Uani 1 1 d . . .
H2A H 0.7006 1.0222 0.4372 0.052 Uiso 1 1 calc R . .
H2B H 0.7014 1.1328 0.5001 0.052 Uiso 1 1 calc R . .
H2C H 0.6672 1.1655 0.4484 0.052 Uiso 1 1 calc R . .
C3 C 0.66910(10) 0.8514(6) 0.48629(17) 0.0235(8) Uani 1 1 d . . .
H3 H 0.6564 0.8986 0.5182 0.028 Uiso 1 1 calc R . .
C4 C 0.64068(10) 0.7498(6) 0.43807(17) 0.0236(8) Uani 1 1 d . . .
C5 C 0.64967(10) 0.6250(7) 0.39275(17) 0.0241(8) Uani 1 1 d . . .
C6 C 0.68743(11) 0.5948(7) 0.38413(18) 0.0273(9) Uani 1 1 d . . .
H6 H 0.7016 0.4829 0.4064 0.033 Uiso 1 1 calc R . .
C7 C 0.70236(11) 0.7154(7) 0.34716(18) 0.0279(9) Uani 1 1 d . . .
H7 H 0.6883 0.8307 0.3262 0.034 Uiso 1 1 calc R . .
C8 C 0.73899(11) 0.6841(7) 0.33613(17) 0.0261(9) Uani 1 1 d . . .
C9 C 0.75901(11) 0.4900(7) 0.35217(18) 0.0292(9) Uani 1 1 d . . .
H9 H 0.7485 0.3695 0.3692 0.035 Uiso 1 1 calc R . .
C10 C 0.79393(12) 0.4727(8) 0.3434(2) 0.0350(10) Uani 1 1 d . . .
H10 H 0.8073 0.3416 0.3551 0.042 Uiso 1 1 calc R . .
C11 C 0.80943(12) 0.6455(8) 0.3177(2) 0.0365(10) Uani 1 1 d . . .
H11 H 0.8335 0.6337 0.3123 0.044 Uiso 1 1 calc R . .
C12 C 0.78976(12) 0.8353(8) 0.2999(2) 0.0357(10) Uani 1 1 d . . .
H12 H 0.8001 0.9521 0.2813 0.043 Uiso 1 1 calc R . .
C13 C 0.75480(11) 0.8555(7) 0.30905(19) 0.0318(9) Uani 1 1 d . . .
H13 H 0.7415 0.9865 0.2969 0.038 Uiso 1 1 calc R . .
C14 C 0.62202(11) 0.5127(6) 0.35258(17) 0.0245(8) Uani 1 1 d . . .
C15 C 0.62829(11) 0.3710(7) 0.30249(18) 0.0283(9) Uani 1 1 d . . .
C16 C 0.59248(12) 0.2484(8) 0.28114(19) 0.0334(10) Uani 1 1 d . . .
C17 C 0.56489(11) 0.3760(7) 0.30934(17) 0.0295(9) Uani 1 1 d . . .
C18 C 0.58639(11) 0.5251(6) 0.35455(16) 0.0239(8) Uani 1 1 d . . .
C19 C 0.48182(13) 0.5134(10) 0.4110(3) 0.0560(15) Uani 1 1 d . . .
H19A H 0.4957 0.3873 0.4301 0.084 Uiso 1 1 calc R . .
H19B H 0.4594 0.4595 0.3870 0.084 Uiso 1 1 calc R . .
H19C H 0.4765 0.6155 0.4411 0.084 Uiso 1 1 calc R . .
C20 C 0.48266(13) 0.8349(9) 0.3423(2) 0.0484(13) Uani 1 1 d . . .
H20A H 0.4795 0.9435 0.3723 0.073 Uiso 1 1 calc R . .
H20B H 0.4592 0.7856 0.3210 0.073 Uiso 1 1 calc R . .
H20C H 0.4959 0.9036 0.3148 0.073 Uiso 1 1 calc R . .
C21 C 0.50361(11) 0.6355(8) 0.3718(2) 0.0359(10) Uani 1 1 d . . .
H21 H 0.5075 0.5307 0.3402 0.043 Uiso 1 1 calc R . .
C22 C 0.53988(11) 0.7051(7) 0.40588(19) 0.0298(9) Uani 1 1 d . . .
C23 C 0.57458(11) 0.6618(7) 0.39761(17) 0.0258(9) Uani 1 1 d . . .
C24 C 0.60248(10) 0.7776(6) 0.43967(17) 0.0229(8) Uani 1 1 d . . .
C25 C 0.58721(10) 0.9050(7) 0.47903(17) 0.0242(8) Uani 1 1 d . . .
C26 C 0.60077(10) 1.0604(7) 0.52795(18) 0.0258(9) Uani 1 1 d . . .
C27 C 0.59870(10) 1.0051(7) 0.58630(17) 0.0258(9) Uani 1 1 d . . .
H27 H 0.5903 0.8625 0.5946 0.031 Uiso 1 1 calc R . .
C28 C 0.60877(11) 1.1552(7) 0.63138(18) 0.0285(9) Uani 1 1 d . . .
H28 H 0.6072 1.1148 0.6704 0.034 Uiso 1 1 calc R . .
C29 C 0.62123(11) 1.3659(7) 0.62034(18) 0.0303(9) Uani 1 1 d . . .
H29 H 0.6283 1.4691 0.6514 0.036 Uiso 1 1 calc R . .
C30 C 0.62316(11) 1.4221(7) 0.56258(19) 0.0310(10) Uani 1 1 d . . .
H30 H 0.6316 1.5650 0.5545 0.037 Uiso 1 1 calc R . .
C31 C 0.61305(11) 1.2738(7) 0.51727(18) 0.0272(9) Uani 1 1 d . . .
H31 H 0.6144 1.3160 0.4783 0.033 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 0.0219(5) 0.0429(6) 0.0364(6) -0.0122(5) 0.0094(4) -0.0011(5)
F1 0.0367(15) 0.0474(16) 0.0396(15) -0.0125(13) 0.0005(12) 0.0161(13)
F2 0.0459(16) 0.0558(17) 0.0232(12) -0.0002(12) 0.0131(12) -0.0073(13)
F3 0.0526(18) 0.0304(15) 0.086(2) -0.0016(15) 0.0215(17) 0.0023(13)
F4 0.0403(16) 0.089(2) 0.0271(14) -0.0233(15) 0.0029(12) -0.0040(16)
F5 0.0400(15) 0.0442(15) 0.0481(16) -0.0136(13) 0.0173(13) -0.0167(13)
F6 0.0387(15) 0.0521(17) 0.0318(14) -0.0081(13) -0.0088(12) 0.0108(13)
C1 0.025(2) 0.038(2) 0.031(2) -0.0066(19) 0.0012(18) 0.0008(18)
C2 0.035(2) 0.032(2) 0.041(3) -0.005(2) 0.014(2) -0.0074(19)
C3 0.0216(19) 0.026(2) 0.0221(19) -0.0016(16) 0.0034(16) -0.0026(16)
C4 0.0230(19) 0.0236(19) 0.0243(19) 0.0003(16) 0.0050(16) -0.0016(16)
C5 0.0212(19) 0.026(2) 0.025(2) 0.0033(17) 0.0051(16) -0.0007(16)
C6 0.023(2) 0.032(2) 0.027(2) -0.0030(18) 0.0052(17) 0.0019(17)
C7 0.026(2) 0.027(2) 0.032(2) 0.0032(18) 0.0089(18) 0.0029(17)
C8 0.025(2) 0.031(2) 0.023(2) -0.0011(17) 0.0069(17) -0.0023(17)
C9 0.029(2) 0.031(2) 0.029(2) -0.0001(18) 0.0078(18) 0.0014(18)
C10 0.030(2) 0.039(2) 0.036(2) -0.002(2) 0.008(2) 0.008(2)
C11 0.026(2) 0.046(3) 0.039(3) -0.001(2) 0.010(2) 0.002(2)
C12 0.032(2) 0.042(3) 0.034(2) 0.004(2) 0.010(2) -0.008(2)
C13 0.029(2) 0.035(2) 0.031(2) 0.0010(19) 0.0074(19) 0.0004(19)
C14 0.028(2) 0.0245(19) 0.0225(19) 0.0005(16) 0.0079(16) 0.0006(17)
C15 0.026(2) 0.033(2) 0.025(2) -0.0007(18) 0.0046(17) 0.0023(18)
C16 0.035(2) 0.037(2) 0.029(2) -0.0066(19) 0.0071(19) 0.004(2)
C17 0.030(2) 0.035(2) 0.022(2) -0.0015(18) 0.0022(17) 0.0005(19)
C18 0.0260(19) 0.026(2) 0.0200(18) -0.0002(16) 0.0043(16) 0.0019(16)
C19 0.029(3) 0.065(4) 0.069(4) 0.014(3) -0.002(2) -0.016(3)
C20 0.032(3) 0.056(3) 0.051(3) 0.002(3) -0.008(2) -0.005(2)
C21 0.023(2) 0.044(3) 0.042(3) -0.009(2) 0.0083(19) -0.001(2)
C22 0.020(2) 0.038(2) 0.031(2) -0.0058(19) 0.0060(17) -0.0035(18)
C23 0.024(2) 0.028(2) 0.026(2) -0.0014(16) 0.0061(17) -0.0020(16)
C24 0.0205(18) 0.026(2) 0.0220(19) 0.0014(16) 0.0044(16) 0.0005(16)
C25 0.0218(19) 0.029(2) 0.0222(19) -0.0005(16) 0.0052(16) 0.0004(16)
C26 0.0201(19) 0.029(2) 0.029(2) -0.0032(17) 0.0084(17) 0.0019(16)
C27 0.024(2) 0.026(2) 0.029(2) 0.0012(17) 0.0082(17) 0.0005(16)
C28 0.028(2) 0.036(2) 0.022(2) 0.0020(18) 0.0065(17) 0.0015(18)
C29 0.030(2) 0.035(2) 0.026(2) -0.0070(18) 0.0060(18) 0.0028(19)
C30 0.033(2) 0.025(2) 0.038(2) -0.0024(18) 0.015(2) -0.0030(18)
C31 0.030(2) 0.030(2) 0.022(2) 0.0004(17) 0.0068(17) 0.0032(18)
_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 C22 1.703(4) . ?
S1 C25 1.712(4) . ?
F1 C15 1.360(5) . ?
F2 C15 1.371(5) . ?
F3 C16 1.349(5) . ?
F4 C16 1.345(5) . ?
F5 C17 1.359(5) . ?
F6 C17 1.381(5) . ?
C1 C3 1.542(6) . ?
C2 C3 1.538(6) . ?
C3 C4 1.524(5) . ?
C4 C5 1.389(5) . ?
C4 C24 1.471(5) . ?
C5 C14 1.432(6) . ?
C5 C6 1.500(5) . ?
C6 C7 1.333(6) . ?
C7 C8 1.477(5) . ?
C8 C13 1.403(6) . ?
C8 C9 1.405(6) . ?
C9 C10 1.387(6) . ?
C10 C11 1.387(6) . ?
C11 C12 1.384(7) . ?
C12 C13 1.393(6) . ?
C14 C18 1.367(5) . ?
C14 C15 1.498(5) . ?
C15 C16 1.544(6) . ?
C16 C17 1.545(6) . ?
C17 C18 1.497(6) . ?
C18 C23 1.433(5) . ?
C19 C21 1.534(7) . ?
C20 C21 1.527(7) . ?
C21 C22 1.510(6) . ?
C22 C23 1.395(5) . ?
C23 C24 1.470(6) . ?
C24 C25 1.403(5) . ?
C25 C26 1.484(5) . ?
C26 C31 1.406(6) . ?
C26 C27 1.412(5) . ?
C27 C28 1.379(6) . ?
C28 C29 1.396(6) . ?
C29 C30 1.399(6) . ?
C30 C31 1.376(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
C22 S1 C25 95.40(19) . . ?
C4 C3 C2 112.9(3) . . ?
C4 C3 C1 113.9(3) . . ?
C2 C3 C1 110.2(3) . . ?
C5 C4 C24 118.1(4) . . ?
C5 C4 C3 122.0(3) . . ?
C24 C4 C3 119.9(3) . . ?
C4 C5 C14 119.4(3) . . ?
C4 C5 C6 123.4(4) . . ?
C14 C5 C6 117.2(3) . . ?
C7 C6 C5 124.1(4) . . ?
C6 C7 C8 125.3(4) . . ?
C13 C8 C9 118.2(4) . . ?
C13 C8 C7 119.0(4) . . ?
C9 C8 C7 122.8(4) . . ?
C10 C9 C8 120.6(4) . . ?
C9 C10 C11 120.5(4) . . ?
C12 C11 C10 119.8(4) . . ?
C11 C12 C13 120.2(4) . . ?
C12 C13 C8 120.7(4) . . ?
C18 C14 C5 124.0(4) . . ?
C18 C14 C15 111.5(4) . . ?
C5 C14 C15 124.5(3) . . ?
F1 C15 F2 105.8(3) . . ?
F1 C15 C14 114.9(3) . . ?
F2 C15 C14 111.8(3) . . ?
F1 C15 C16 110.3(3) . . ?
F2 C15 C16 109.1(3) . . ?
C14 C15 C16 104.9(3) . . ?
F4 C16 F3 107.3(4) . . ?
F4 C16 C15 112.4(4) . . ?
F3 C16 C15 109.6(4) . . ?
F4 C16 C17 112.8(4) . . ?
F3 C16 C17 109.8(4) . . ?
C15 C16 C17 104.8(3) . . ?
F5 C17 F6 105.5(3) . . ?
F5 C17 C18 114.5(3) . . ?
F6 C17 C18 112.4(4) . . ?
F5 C17 C16 110.1(4) . . ?
F6 C17 C16 108.6(3) . . ?
C18 C17 C16 105.8(3) . . ?
C14 C18 C23 120.2(4) . . ?
C14 C18 C17 110.7(3) . . ?
C23 C18 C17 129.1(4) . . ?
C22 C21 C20 111.1(4) . . ?
C22 C21 C19 111.5(4) . . ?
C20 C21 C19 110.3(4) . . ?
C23 C22 C21 132.0(4) . . ?
C23 C22 S1 109.6(3) . . ?
C21 C22 S1 118.4(3) . . ?
C22 C23 C18 129.6(4) . . ?
C22 C23 C24 113.6(3) . . ?
C18 C23 C24 116.8(3) . . ?
C25 C24 C23 110.8(3) . . ?
C25 C24 C4 128.0(4) . . ?
C23 C24 C4 121.2(3) . . ?
C24 C25 C26 135.8(4) . . ?
C24 C25 S1 110.6(3) . . ?
C26 C25 S1 113.5(3) . . ?
C31 C26 C27 117.9(4) . . ?
C31 C26 C25 121.3(4) . . ?
C27 C26 C25 120.6(4) . . ?
C28 C27 C26 120.9(4) . . ?
C27 C28 C29 120.7(4) . . ?
C28 C29 C30 118.6(4) . . ?
C31 C30 C29 121.1(4) . . ?
C30 C31 C26 120.8(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
C2 C3 C4 C5 77.5(5) . . . . ?
C1 C3 C4 C5 -49.3(5) . . . . ?
C2 C3 C4 C24 -104.3(4) . . . . ?
C1 C3 C4 C24 129.0(4) . . . . ?
C24 C4 C5 C14 -5.4(6) . . . . ?
C3 C4 C5 C14 172.9(4) . . . . ?
C24 C4 C5 C6 176.4(4) . . . . ?
C3 C4 C5 C6 -5.3(6) . . . . ?
C4 C5 C6 C7 -96.9(5) . . . . ?
C14 C5 C6 C7 84.8(5) . . . . ?
C5 C6 C7 C8 -177.6(4) . . . . ?
C6 C7 C8 C13 -162.9(4) . . . . ?
C6 C7 C8 C9 16.4(7) . . . . ?
C13 C8 C9 C10 2.4(6) . . . . ?
C7 C8 C9 C10 -176.9(4) . . . . ?
C8 C9 C10 C11 -1.1(7) . . . . ?
C9 C10 C11 C12 -1.0(7) . . . . ?
C10 C11 C12 C13 1.7(7) . . . . ?
C11 C12 C13 C8 -0.3(7) . . . . ?
C9 C8 C13 C12 -1.7(6) . . . . ?
C7 C8 C13 C12 177.7(4) . . . . ?
C4 C5 C14 C18 2.1(6) . . . . ?
C6 C5 C14 C18 -179.6(4) . . . . ?
C4 C5 C14 C15 -179.2(4) . . . . ?
C6 C5 C14 C15 -0.9(6) . . . . ?
C18 C14 C15 F1 -134.3(4) . . . . ?
C5 C14 C15 F1 46.8(5) . . . . ?
C18 C14 C15 F2 105.0(4) . . . . ?
C5 C14 C15 F2 -73.9(5) . . . . ?
C18 C14 C15 C16 -13.1(5) . . . . ?
C5 C14 C15 C16 168.1(4) . . . . ?
F1 C15 C16 F4 -97.7(4) . . . . ?
F2 C15 C16 F4 18.1(5) . . . . ?
C14 C15 C16 F4 138.0(4) . . . . ?
F1 C15 C16 F3 21.5(5) . . . . ?
F2 C15 C16 F3 137.3(3) . . . . ?
C14 C15 C16 F3 -102.7(4) . . . . ?
F1 C15 C16 C17 139.4(3) . . . . ?
F2 C15 C16 C17 -104.8(4) . . . . ?
C14 C15 C16 C17 15.1(4) . . . . ?
F4 C16 C17 F5 100.8(4) . . . . ?
F3 C16 C17 F5 -18.8(5) . . . . ?
C15 C16 C17 F5 -136.6(3) . . . . ?
F4 C16 C17 F6 -14.2(5) . . . . ?
F3 C16 C17 F6 -133.8(4) . . . . ?
C15 C16 C17 F6 108.5(4) . . . . ?
F4 C16 C17 C18 -135.0(4) . . . . ?
F3 C16 C17 C18 105.3(4) . . . . ?
C15 C16 C17 C18 -12.4(4) . . . . ?
C5 C14 C18 C23 1.9(6) . . . . ?
C15 C14 C18 C23 -176.9(3) . . . . ?
C5 C14 C18 C17 -175.9(4) . . . . ?
C15 C14 C18 C17 5.3(5) . . . . ?
F5 C17 C18 C14 126.2(4) . . . . ?
F6 C17 C18 C14 -113.5(4) . . . . ?
C16 C17 C18 C14 4.8(5) . . . . ?
F5 C17 C18 C23 -51.3(6) . . . . ?
F6 C17 C18 C23 68.9(5) . . . . ?
C16 C17 C18 C23 -172.7(4) . . . . ?
C20 C21 C22 C23 -112.9(6) . . . . ?
C19 C21 C22 C23 123.6(5) . . . . ?
C20 C21 C22 S1 63.4(5) . . . . ?
C19 C21 C22 S1 -60.1(5) . . . . ?
C25 S1 C22 C23 0.6(3) . . . . ?
C25 S1 C22 C21 -176.5(4) . . . . ?
C21 C22 C23 C18 -3.5(8) . . . . ?
S1 C22 C23 C18 179.9(4) . . . . ?
C21 C22 C23 C24 175.9(4) . . . . ?
S1 C22 C23 C24 -0.7(5) . . . . ?
C14 C18 C23 C22 177.2(4) . . . . ?
C17 C18 C23 C22 -5.5(7) . . . . ?
C14 C18 C23 C24 -2.2(6) . . . . ?
C17 C18 C23 C24 175.1(4) . . . . ?
C22 C23 C24 C25 0.4(5) . . . . ?
C18 C23 C24 C25 179.9(3) . . . . ?
C22 C23 C24 C4 179.3(4) . . . . ?
C18 C23 C24 C4 -1.2(5) . . . . ?
C5 C4 C24 C25 -176.3(4) . . . . ?
C3 C4 C24 C25 5.4(6) . . . . ?
C5 C4 C24 C23 5.1(6) . . . . ?
C3 C4 C24 C23 -173.3(4) . . . . ?
C23 C24 C25 C26 -176.9(4) . . . . ?
C4 C24 C25 C26 4.4(8) . . . . ?
C23 C24 C25 S1 0.0(4) . . . . ?
C4 C24 C25 S1 -178.7(3) . . . . ?
C22 S1 C25 C24 -0.3(3) . . . . ?
C22 S1 C25 C26 177.3(3) . . . . ?
C24 C25 C26 C31 72.3(6) . . . . ?
S1 C25 C26 C31 -104.5(4) . . . . ?
C24 C25 C26 C27 -113.4(5) . . . . ?
S1 C25 C26 C27 69.8(4) . . . . ?
C31 C26 C27 C28 -0.6(6) . . . . ?
C25 C26 C27 C28 -175.1(4) . . . . ?
C26 C27 C28 C29 0.1(6) . . . . ?
C27 C28 C29 C30 0.3(6) . . . . ?
C28 C29 C30 C31 0.0(6) . . . . ?
C29 C30 C31 C26 -0.6(6) . . . . ?
C27 C26 C31 C30 0.9(6) . . . . ?
C25 C26 C31 C30 175.3(4) . . . . ?
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.44
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.086