# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1550944'
_audit_update_record             
;
2017-05-18 deposited with the CCDC.
2017-08-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'triphenylsulfonium trifluoromethanesulfonate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H15 F3 O3 S2'
_chemical_formula_weight         412.43

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'
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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7640(8)
_cell_length_b                   10.0110(8)
_cell_length_c                   11.2134(10)
_cell_angle_alpha                99.004(4)
_cell_angle_beta                 91.663(5)
_cell_angle_gamma                98.870(4)
_cell_volume                     958.65(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9328
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      23.5

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_absorpt_coefficient_mu    0.322
_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      296(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  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            31848
_diffrn_reflns_av_R_equivalents  0.0682
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         27.78
_reflns_number_total             4457
_reflns_number_gt                3508
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_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 F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4457
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1572
_refine_ls_R_factor_gt           0.1377
_refine_ls_wR_factor_ref         0.4205
_refine_ls_wR_factor_gt          0.4083
_refine_ls_goodness_of_fit_ref   3.083
_refine_ls_restrained_S_all      3.083
_refine_ls_shift/su_max          0.029
_refine_ls_shift/su_mean         0.012

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
C1 C 0.5777(7) 0.7064(6) 0.7569(5) 0.0454(13) Uani 1 1 d . . .
C2 C 0.6768(9) 0.6974(8) 0.8523(7) 0.0664(18) Uani 1 1 d . . .
H2A H 0.6436 0.6465 0.9120 0.080 Uiso 1 1 calc R . .
C3 C 0.6261(8) 0.7820(7) 0.6706(7) 0.0616(17) Uani 1 1 d . . .
H3A H 0.5590 0.7890 0.6070 0.074 Uiso 1 1 calc R . .
C4 C 0.7821(10) 0.8505(8) 0.6799(9) 0.081(2) Uani 1 1 d . . .
H4A H 0.8183 0.9019 0.6213 0.097 Uiso 1 1 calc R . .
C5 C 0.8279(10) 0.7670(10) 0.8566(10) 0.091(3) Uani 1 1 d . . .
H5A H 0.8965 0.7612 0.9197 0.109 Uiso 1 1 calc R . .
C6 C 0.8761(9) 0.8409(8) 0.7730(11) 0.082(3) Uani 1 1 d . . .
H6A H 0.9774 0.8870 0.7791 0.099 Uiso 1 1 calc R . .
C7 C 0.2858(6) 0.6357(6) 0.6263(5) 0.0414(12) Uani 1 1 d . . .
C8 C 0.2611(8) 0.5248(7) 0.5316(6) 0.0580(16) Uani 1 1 d . . .
H8A H 0.2977 0.4439 0.5391 0.070 Uiso 1 1 calc R . .
C9 C 0.2306(8) 0.7569(7) 0.6183(6) 0.0602(16) Uani 1 1 d . . .
H9A H 0.2478 0.8303 0.6818 0.072 Uiso 1 1 calc R . .
C10 C 0.1486(9) 0.7652(8) 0.5124(7) 0.0664(18) Uani 1 1 d . . .
H10A H 0.1093 0.8449 0.5049 0.080 Uiso 1 1 calc R . .
C11 C 0.1821(9) 0.5369(8) 0.4274(6) 0.070(2) Uani 1 1 d . . .
H11A H 0.1666 0.4650 0.3626 0.084 Uiso 1 1 calc R . .
C12 C 0.1253(8) 0.6578(9) 0.4197(6) 0.0670(19) Uani 1 1 d . . .
H12A H 0.0703 0.6654 0.3495 0.080 Uiso 1 1 calc R . .
C13 C 0.3065(6) 0.6889(5) 0.8834(5) 0.0402(11) Uani 1 1 d . . .
C14 C 0.2182(8) 0.6038(7) 0.9485(6) 0.0560(15) Uani 1 1 d . . .
H14A H 0.2044 0.5092 0.9251 0.067 Uiso 1 1 calc R . .
C15 C 0.3313(8) 0.8330(6) 0.9191(6) 0.0563(15) Uani 1 1 d . . .
H15A H 0.3941 0.8895 0.8758 0.068 Uiso 1 1 calc R . .
C16 C 0.1494(9) 0.6620(8) 1.0509(6) 0.068(2) Uani 1 1 d . . .
H16A H 0.0888 0.6064 1.0963 0.082 Uiso 1 1 calc R . .
C17 C 0.2626(8) 0.8861(7) 1.0163(6) 0.0627(17) Uani 1 1 d . . .
H17A H 0.2753 0.9807 1.0392 0.075 Uiso 1 1 calc R . .
C18 C 0.1721(8) 0.8014(8) 1.0838(6) 0.0654(18) Uani 1 1 d . . .
H18A H 0.1266 0.8402 1.1519 0.078 Uiso 1 1 calc R . .
C19 C -0.4280(10) 0.7963(11) 0.2752(12) 0.100(3) Uani 1 1 d . . .
S1 S 0.39023(16) 0.60720(13) 0.75493(12) 0.0417(5) Uani 1 1 d . . .
S2 S -0.2269(2) 0.81967(17) 0.2562(2) 0.0673(6) Uani 1 1 d . . .
O1 O -0.2056(11) 0.9124(11) 0.1755(12) 0.175(5) Uani 1 1 d . . .
O2 O -0.1628(11) 0.8982(11) 0.3646(12) 0.183(6) Uani 1 1 d . . .
O3 O -0.1810(7) 0.6964(6) 0.2253(9) 0.110(3) Uani 1 1 d . . .
F1 F -0.4877(8) 0.9025(7) 0.2909(11) 0.176(4) Uani 1 1 d . . .
F2 F -0.4669(9) 0.7163(8) 0.3595(8) 0.155(3) Uani 1 1 d . . .
F3 F -0.4985(10) 0.7066(10) 0.1766(12) 0.201(5) 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 C3 1.357(9) . ?
C1 C2 1.381(9) . ?
C1 S1 1.782(6) . ?
C2 C5 1.394(12) . ?
C2 H2A 0.9300 . ?
C3 C4 1.424(10) . ?
C3 H3A 0.9300 . ?
C4 C6 1.335(14) . ?
C4 H4A 0.9300 . ?
C5 C6 1.322(14) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C9 1.388(8) . ?
C7 C8 1.397(8) . ?
C7 S1 1.770(5) . ?
C8 C11 1.372(10) . ?
C8 H8A 0.9300 . ?
C9 C10 1.391(10) . ?
C9 H9A 0.9300 . ?
C10 C12 1.360(11) . ?
C10 H10A 0.9300 . ?
C11 C12 1.392(11) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
C13 C14 1.372(8) . ?
C13 C15 1.416(8) . ?
C13 S1 1.778(5) . ?
C14 C16 1.401(10) . ?
C14 H14A 0.9300 . ?
C15 C17 1.338(10) . ?
C15 H15A 0.9300 . ?
C16 C18 1.368(11) . ?
C16 H16A 0.9300 . ?
C17 C18 1.396(10) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
C19 F1 1.247(11) . ?
C19 F3 1.375(15) . ?
C19 F2 1.350(12) . ?
C19 S2 1.765(9) . ?
S2 O3 1.354(6) . ?
S2 O2 1.391(10) . ?
S2 O1 1.391(9) . ?

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
C3 C1 C2 120.8(6) . . ?
C3 C1 S1 124.3(5) . . ?
C2 C1 S1 114.8(5) . . ?
C1 C2 C5 118.1(8) . . ?
C1 C2 H2A 121.0 . . ?
C5 C2 H2A 121.0 . . ?
C1 C3 C4 118.5(7) . . ?
C1 C3 H3A 120.8 . . ?
C4 C3 H3A 120.8 . . ?
C6 C4 C3 119.9(8) . . ?
C6 C4 H4A 120.1 . . ?
C3 C4 H4A 120.0 . . ?
C6 C5 C2 121.6(8) . . ?
C6 C5 H5A 119.2 . . ?
C2 C5 H5A 119.2 . . ?
C4 C6 C5 121.2(7) . . ?
C4 C6 H6A 119.4 . . ?
C5 C6 H6A 119.4 . . ?
C9 C7 C8 121.7(5) . . ?
C9 C7 S1 123.8(4) . . ?
C8 C7 S1 114.5(4) . . ?
C11 C8 C7 119.0(6) . . ?
C11 C8 H8A 120.5 . . ?
C7 C8 H8A 120.5 . . ?
C10 C9 C7 117.9(6) . . ?
C10 C9 H9A 121.0 . . ?
C7 C9 H9A 121.0 . . ?
C9 C10 C12 120.5(7) . . ?
C9 C10 H10A 119.7 . . ?
C12 C10 H10A 119.7 . . ?
C12 C11 C8 119.4(6) . . ?
C12 C11 H11A 120.3 . . ?
C8 C11 H11A 120.3 . . ?
C11 C12 C10 121.5(6) . . ?
C11 C12 H12A 119.3 . . ?
C10 C12 H12A 119.3 . . ?
C14 C13 C15 121.4(5) . . ?
C14 C13 S1 116.0(4) . . ?
C15 C13 S1 122.6(4) . . ?
C13 C14 C16 118.7(6) . . ?
C13 C14 H14A 120.6 . . ?
C16 C14 H14A 120.7 . . ?
C17 C15 C13 118.7(6) . . ?
C17 C15 H15A 120.7 . . ?
C13 C15 H15A 120.6 . . ?
C18 C16 C14 119.5(6) . . ?
C18 C16 H16A 120.2 . . ?
C14 C16 H16A 120.2 . . ?
C15 C17 C18 120.8(6) . . ?
C15 C17 H17A 119.6 . . ?
C18 C17 H17A 119.6 . . ?
C16 C18 C17 120.8(6) . . ?
C16 C18 H18A 119.6 . . ?
C17 C18 H18A 119.6 . . ?
F1 C19 F3 110.6(10) . . ?
F1 C19 F2 112.2(11) . . ?
F3 C19 F2 97.4(9) . . ?
F1 C19 S2 116.0(8) . . ?
F3 C19 S2 107.6(9) . . ?
F2 C19 S2 111.4(7) . . ?
C7 S1 C13 106.6(2) . . ?
C7 S1 C1 106.4(3) . . ?
C13 S1 C1 103.7(2) . . ?
O3 S2 O2 116.4(7) . . ?
O3 S2 O1 118.2(7) . . ?
O2 S2 O1 102.7(8) . . ?
O3 S2 C19 109.7(5) . . ?
O2 S2 C19 104.3(6) . . ?
O1 S2 C19 103.9(6) . . ?

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
C3 C1 C2 C5 -0.7(10) . . . . ?
S1 C1 C2 C5 176.9(6) . . . . ?
C2 C1 C3 C4 0.9(10) . . . . ?
S1 C1 C3 C4 -176.6(5) . . . . ?
C1 C3 C4 C6 -1.0(11) . . . . ?
C1 C2 C5 C6 0.7(13) . . . . ?
C3 C4 C6 C5 1.0(12) . . . . ?
C2 C5 C6 C4 -0.9(14) . . . . ?
C9 C7 C8 C11 1.0(10) . . . . ?
S1 C7 C8 C11 -179.6(5) . . . . ?
C8 C7 C9 C10 0.1(10) . . . . ?
S1 C7 C9 C10 -179.3(5) . . . . ?
C7 C9 C10 C12 -0.6(11) . . . . ?
C7 C8 C11 C12 -1.6(11) . . . . ?
C8 C11 C12 C10 1.1(12) . . . . ?
C9 C10 C12 C11 0.0(12) . . . . ?
C15 C13 C14 C16 1.3(10) . . . . ?
S1 C13 C14 C16 179.8(5) . . . . ?
C14 C13 C15 C17 -2.2(10) . . . . ?
S1 C13 C15 C17 179.4(5) . . . . ?
C13 C14 C16 C18 -0.3(11) . . . . ?
C13 C15 C17 C18 2.0(11) . . . . ?
C14 C16 C18 C17 0.1(12) . . . . ?
C15 C17 C18 C16 -1.1(12) . . . . ?
C9 C7 S1 C13 37.2(6) . . . . ?
C8 C7 S1 C13 -142.2(5) . . . . ?
C9 C7 S1 C1 -73.0(6) . . . . ?
C8 C7 S1 C1 107.6(5) . . . . ?
C14 C13 S1 C7 107.0(5) . . . . ?
C15 C13 S1 C7 -74.5(5) . . . . ?
C14 C13 S1 C1 -140.9(5) . . . . ?
C15 C13 S1 C1 37.6(6) . . . . ?
C3 C1 S1 C7 -2.7(6) . . . . ?
C2 C1 S1 C7 179.8(5) . . . . ?
C3 C1 S1 C13 -114.9(6) . . . . ?
C2 C1 S1 C13 67.6(5) . . . . ?
F1 C19 S2 O3 -172.5(11) . . . . ?
F3 C19 S2 O3 -48.0(9) . . . . ?
F2 C19 S2 O3 57.6(11) . . . . ?
F1 C19 S2 O2 62.1(13) . . . . ?
F3 C19 S2 O2 -173.5(9) . . . . ?
F2 C19 S2 O2 -67.8(11) . . . . ?
F1 C19 S2 O1 -45.1(13) . . . . ?
F3 C19 S2 O1 79.3(10) . . . . ?
F2 C19 S2 O1 -175.1(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        27.78
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         1.347
_refine_diff_density_min         -1.123
_refine_diff_density_rms         0.158

####################################################################### 
# 
# 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_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1550940'
_audit_update_record             
;
2017-05-18 deposited with the CCDC.
2017-08-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'bis(4-methoxyphenyl)(phenyl)sulfonium trifluoromethanesulfonate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H19 F3 O5 S2'
_chemical_formula_weight         472.48

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'
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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   8.9672(3)
_cell_length_b                   22.0738(6)
_cell_length_c                   11.2978(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.418(2)
_cell_angle_gamma                90.00
_cell_volume                     2206.14(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9885
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      21.5

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_absorpt_coefficient_mu    0.296
_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      296(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  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            74064
_diffrn_reflns_av_R_equivalents  0.0732
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         27.58
_reflns_number_total             5097
_reflns_number_gt                3178
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_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 F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5097
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1481
_refine_ls_R_factor_gt           0.1026
_refine_ls_wR_factor_ref         0.3336
_refine_ls_wR_factor_gt          0.3042
_refine_ls_goodness_of_fit_ref   2.152
_refine_ls_restrained_S_all      2.152
_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 0.94937(13) 0.22731(5) 0.72934(9) 0.0681(4) Uani 1 1 d . . .
S2 S 1.6541(2) 0.38748(8) 0.78209(15) 0.1117(6) Uani 1 1 d . . .
O3 O 1.2229(4) 0.38368(14) 0.4022(3) 0.0882(10) Uani 1 1 d . . .
C9 C 1.0887(5) 0.17077(17) 0.7663(3) 0.0581(9) Uani 1 1 d . . .
C1 C 1.0195(5) 0.27521(17) 0.6259(4) 0.0659(11) Uani 1 1 d . . .
C11 C 1.1119(5) 0.14957(17) 0.8822(3) 0.0602(10) Uani 1 1 d . . .
H11A H 1.0570 0.1658 0.9377 0.072 Uiso 1 1 calc R . .
O4 O 1.3911(3) 0.03440(14) 0.8726(3) 0.0818(9) Uani 1 1 d . . .
C6 C 1.1573(5) 0.34959(19) 0.4810(4) 0.0709(11) Uani 1 1 d . . .
C13 C 1.2151(5) 0.10479(18) 0.9166(4) 0.0662(11) Uani 1 1 d . . .
H13A H 1.2320 0.0912 0.9956 0.079 Uiso 1 1 calc R . .
C14 C 1.2954(4) 0.07940(18) 0.8324(4) 0.0616(10) Uani 1 1 d . . .
C12 C 1.2750(5) 0.1030(2) 0.7163(4) 0.0725(12) Uani 1 1 d . . .
H12A H 1.3307 0.0873 0.6608 0.087 Uiso 1 1 calc R . .
C3 C 1.0973(6) 0.3254(2) 0.6729(4) 0.0830(14) Uani 1 1 d . . .
H3A H 1.1037 0.3342 0.7540 0.100 Uiso 1 1 calc R . .
C2 C 1.0042(6) 0.26257(18) 0.5034(3) 0.0701(12) Uani 1 1 d . . .
H2A H 0.9478 0.2295 0.4704 0.084 Uiso 1 1 calc R . .
C4 C 1.0747(6) 0.30007(19) 0.4329(4) 0.0773(13) Uani 1 1 d . . .
H4A H 1.0666 0.2920 0.3513 0.093 Uiso 1 1 calc R . .
C10 C 1.1747(5) 0.1486(2) 0.6832(3) 0.0722(12) Uani 1 1 d . . .
H10A H 1.1636 0.1648 0.6063 0.087 Uiso 1 1 calc R . .
C16 C 0.7913(5) 0.1885(2) 0.6424(4) 0.0739(13) Uani 1 1 d . . .
C5 C 1.1657(6) 0.3628(2) 0.6011(4) 0.0858(14) Uani 1 1 d . . .
H5A H 1.2178 0.3970 0.6333 0.103 Uiso 1 1 calc R . .
O1 O 1.6914(6) 0.3440(2) 0.8675(4) 0.1335(16) Uani 1 1 d . . .
F1 F 1.4085(6) 0.4048(4) 0.8561(6) 0.258(4) Uani 1 1 d . . .
C19 C 0.6613(7) 0.2223(3) 0.6111(5) 0.1016(18) Uani 1 1 d . . .
H19A H 0.6553 0.2626 0.6341 0.122 Uiso 1 1 calc R . .
C18 C 0.6711(9) 0.1022(4) 0.5435(6) 0.120(2) Uani 1 1 d . . .
H18A H 0.6755 0.0617 0.5215 0.144 Uiso 1 1 calc R . .
C17 C 0.7979(6) 0.1297(3) 0.6116(5) 0.0899(15) Uani 1 1 d . . .
H17A H 0.8859 0.1075 0.6354 0.108 Uiso 1 1 calc R . .
C22 C 1.5313(11) 0.4372(4) 0.8395(6) 0.136(3) Uani 1 1 d . . .
C8 C 1.3019(7) 0.4365(2) 0.4462(5) 0.0978(16) Uani 1 1 d . . .
H8A H 1.3414 0.4561 0.3821 0.147 Uiso 1 1 calc R . .
H8B H 1.3836 0.4257 0.5086 0.147 Uiso 1 1 calc R . .
H8C H 1.2342 0.4635 0.4777 0.147 Uiso 1 1 calc R . .
C15 C 1.4679(6) 0.0045(2) 0.7892(6) 0.1012(17) Uani 1 1 d . . .
H15A H 1.5321 -0.0264 0.8297 0.152 Uiso 1 1 calc R . .
H15B H 1.5280 0.0333 0.7542 0.152 Uiso 1 1 calc R . .
H15C H 1.3954 -0.0135 0.7273 0.152 Uiso 1 1 calc R . .
O2 O 1.5731(7) 0.3712(3) 0.6664(4) 0.180(3) Uani 1 1 d . . .
F2 F 1.4850(8) 0.4813(3) 0.7742(6) 0.218(3) Uani 1 1 d . . .
F3 F 1.5915(10) 0.4565(3) 0.9484(5) 0.247(4) Uani 1 1 d . . .
C20 C 0.5367(7) 0.1919(4) 0.5411(6) 0.122(3) Uani 1 1 d . . .
H20A H 0.4473 0.2130 0.5163 0.147 Uiso 1 1 calc R . .
C21 C 0.5459(8) 0.1333(4) 0.5105(6) 0.123(3) Uani 1 1 d . . .
H21A H 0.4626 0.1145 0.4654 0.148 Uiso 1 1 calc R . .
O6 O 1.7767(8) 0.4288(5) 0.7732(11) 0.311(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
S1 C9 1.767(4) . ?
S1 C1 1.766(4) . ?
S1 C16 1.803(5) . ?
S2 O1 1.364(4) . ?
S2 O6 1.444(7) . ?
S2 O2 1.433(5) . ?
S2 C22 1.753(8) . ?
O3 C6 1.370(5) . ?
O3 C8 1.411(6) . ?
C9 C11 1.374(5) . ?
C9 C10 1.397(5) . ?
C1 C3 1.370(6) . ?
C1 C2 1.396(5) . ?
C11 C13 1.366(6) . ?
C11 H11A 0.9300 . ?
O4 C14 1.343(5) . ?
O4 C15 1.417(6) . ?
C6 C5 1.377(6) . ?
C6 C4 1.381(6) . ?
C13 C14 1.400(6) . ?
C13 H13A 0.9300 . ?
C14 C12 1.394(6) . ?
C12 C10 1.361(6) . ?
C12 H12A 0.9300 . ?
C3 C5 1.370(7) . ?
C3 H3A 0.9300 . ?
C2 C4 1.372(6) . ?
C2 H2A 0.9300 . ?
C4 H4A 0.9300 . ?
C10 H10A 0.9300 . ?
C16 C17 1.348(7) . ?
C16 C19 1.381(7) . ?
C5 H5A 0.9300 . ?
F1 C22 1.350(10) . ?
C19 C20 1.427(9) . ?
C19 H19A 0.9300 . ?
C18 C21 1.317(10) . ?
C18 C17 1.402(8) . ?
C18 H18A 0.9300 . ?
C17 H17A 0.9300 . ?
C22 F2 1.251(8) . ?
C22 F3 1.330(8) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C20 C21 1.345(10) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?

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
C9 S1 C1 105.34(18) . . ?
C9 S1 C16 104.8(2) . . ?
C1 S1 C16 104.9(2) . . ?
O1 S2 O6 113.1(4) . . ?
O1 S2 O2 119.9(4) . . ?
O6 S2 O2 111.9(6) . . ?
O1 S2 C22 106.0(3) . . ?
O6 S2 C22 99.4(6) . . ?
O2 S2 C22 103.8(4) . . ?
C6 O3 C8 118.0(4) . . ?
C11 C9 C10 120.4(4) . . ?
C11 C9 S1 117.2(3) . . ?
C10 C9 S1 122.4(3) . . ?
C3 C1 C2 120.5(4) . . ?
C3 C1 S1 116.2(3) . . ?
C2 C1 S1 123.3(3) . . ?
C13 C11 C9 120.5(4) . . ?
C13 C11 H11A 119.8 . . ?
C9 C11 H11A 119.8 . . ?
C14 O4 C15 118.2(4) . . ?
O3 C6 C5 124.3(4) . . ?
O3 C6 C4 116.0(4) . . ?
C5 C6 C4 119.6(4) . . ?
C11 C13 C14 119.7(4) . . ?
C11 C13 H13A 120.1 . . ?
C14 C13 H13A 120.1 . . ?
O4 C14 C12 124.9(4) . . ?
O4 C14 C13 115.9(3) . . ?
C12 C14 C13 119.1(4) . . ?
C10 C12 C14 120.9(4) . . ?
C10 C12 H12A 119.6 . . ?
C14 C12 H12A 119.6 . . ?
C5 C3 C1 120.4(4) . . ?
C5 C3 H3A 119.8 . . ?
C1 C3 H3A 119.8 . . ?
C4 C2 C1 118.4(4) . . ?
C4 C2 H2A 120.8 . . ?
C1 C2 H2A 120.8 . . ?
C2 C4 C6 121.1(4) . . ?
C2 C4 H4A 119.4 . . ?
C6 C4 H4A 119.4 . . ?
C12 C10 C9 119.2(4) . . ?
C12 C10 H10A 120.4 . . ?
C9 C10 H10A 120.4 . . ?
C17 C16 C19 121.7(5) . . ?
C17 C16 S1 122.3(4) . . ?
C19 C16 S1 116.0(5) . . ?
C3 C5 C6 119.9(5) . . ?
C3 C5 H5A 120.1 . . ?
C6 C5 H5A 120.1 . . ?
C16 C19 C20 116.1(6) . . ?
C16 C19 H19A 122.0 . . ?
C20 C19 H19A 122.0 . . ?
C21 C18 C17 120.5(7) . . ?
C21 C18 H18A 119.8 . . ?
C17 C18 H18A 119.8 . . ?
C16 C17 C18 119.5(6) . . ?
C16 C17 H17A 120.2 . . ?
C18 C17 H17A 120.2 . . ?
F2 C22 F3 110.0(8) . . ?
F2 C22 F1 107.1(9) . . ?
F3 C22 F1 104.9(8) . . ?
F2 C22 S2 115.9(6) . . ?
F3 C22 S2 111.0(7) . . ?
F1 C22 S2 107.2(6) . . ?
O3 C8 H8A 109.5 . . ?
O3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 C20 C19 121.4(6) . . ?
C21 C20 H20A 119.3 . . ?
C19 C20 H20A 119.3 . . ?
C18 C21 C20 120.9(7) . . ?
C18 C21 H21A 119.6 . . ?
C20 C21 H21A 119.6 . . ?

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
C1 S1 C9 C11 144.5(3) . . . . ?
C16 S1 C9 C11 -105.1(3) . . . . ?
C1 S1 C9 C10 -34.4(4) . . . . ?
C16 S1 C9 C10 76.0(4) . . . . ?
C9 S1 C1 C3 -94.5(4) . . . . ?
C16 S1 C1 C3 155.2(4) . . . . ?
C9 S1 C1 C2 82.8(4) . . . . ?
C16 S1 C1 C2 -27.5(4) . . . . ?
C10 C9 C11 C13 -2.7(6) . . . . ?
S1 C9 C11 C13 178.4(3) . . . . ?
C8 O3 C6 C5 -1.3(7) . . . . ?
C8 O3 C6 C4 176.8(4) . . . . ?
C9 C11 C13 C14 -1.4(6) . . . . ?
C15 O4 C14 C12 -6.1(6) . . . . ?
C15 O4 C14 C13 176.0(4) . . . . ?
C11 C13 C14 O4 -178.0(4) . . . . ?
C11 C13 C14 C12 3.9(6) . . . . ?
O4 C14 C12 C10 179.8(4) . . . . ?
C13 C14 C12 C10 -2.4(7) . . . . ?
C2 C1 C3 C5 -2.3(7) . . . . ?
S1 C1 C3 C5 175.0(4) . . . . ?
C3 C1 C2 C4 2.9(7) . . . . ?
S1 C1 C2 C4 -174.3(3) . . . . ?
C1 C2 C4 C6 -0.7(7) . . . . ?
O3 C6 C4 C2 179.8(4) . . . . ?
C5 C6 C4 C2 -2.0(7) . . . . ?
C14 C12 C10 C9 -1.6(7) . . . . ?
C11 C9 C10 C12 4.2(7) . . . . ?
S1 C9 C10 C12 -176.9(4) . . . . ?
C9 S1 C16 C17 -4.1(4) . . . . ?
C1 S1 C16 C17 106.6(4) . . . . ?
C9 S1 C16 C19 174.6(3) . . . . ?
C1 S1 C16 C19 -74.7(3) . . . . ?
C1 C3 C5 C6 -0.5(8) . . . . ?
O3 C6 C5 C3 -179.4(4) . . . . ?
C4 C6 C5 C3 2.6(7) . . . . ?
C17 C16 C19 C20 -2.0(7) . . . . ?
S1 C16 C19 C20 179.3(3) . . . . ?
C19 C16 C17 C18 1.6(8) . . . . ?
S1 C16 C17 C18 -179.8(4) . . . . ?
C21 C18 C17 C16 -0.6(9) . . . . ?
O1 S2 C22 F2 179.2(7) . . . . ?
O6 S2 C22 F2 61.8(9) . . . . ?
O2 S2 C22 F2 -53.7(9) . . . . ?
O1 S2 C22 F3 52.8(8) . . . . ?
O6 S2 C22 F3 -64.7(8) . . . . ?
O2 S2 C22 F3 179.9(7) . . . . ?
O1 S2 C22 F1 -61.3(6) . . . . ?
O6 S2 C22 F1 -178.7(6) . . . . ?
O2 S2 C22 F1 65.8(6) . . . . ?
C16 C19 C20 C21 1.4(8) . . . . ?
C17 C18 C21 C20 0.0(10) . . . . ?
C19 C20 C21 C18 -0.5(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.58
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.313
_refine_diff_density_min         -0.703
_refine_diff_density_rms         0.077

