# Supplementary Material (ESI) for Perkin Transactions
# This journal is © The Royal Society of Chemistry 2000
# CCDC Number: 207/445

data_global

_publ_contact_author
;
   Alexander Kolomeitsev
   Institut of Organic Chemistry
   Ukrainian Academy of Sciences
   Kiev
   Ukraine
;
_publ_contact_author_fax     '049 421 218 4267'

_publ_requested_journal      'Perkins Transactions'

_publ_section_title
;
Synthesis, Structure and Reactivity of a Trifluoromethyl
Sulfide Anionic Salt Stabilized with Tetrakis(dimethyamino)-
ethylene Dication (TDAE2+)
;

loop_
_publ_author_name
_publ_author_address
  'Alexander Kolomeitsev'
;  Institut of Organic Chemistry 
   Ukrainian Academy of Sciences 
   Kiev 
   Ukraine 
;
  'Medebilee, Maurice'
;  Universite Paris, Electrochimie Moleculaire
   2,Place Jussieu
   F-75251 Paris  
   France 
;
  'Kirsch, Peer'
;  Merck KGaA
   Liquid Crystals Division
   Frankfurter Strasse 250
   D-64271 Darmstadt
   Germany
;
  'Dr. Lork, Enno'
;  Institut of Inorganic and Physical Chemistry
   University of Bremen
   Leobener Str.
   D-28359 Bremen
   Germany
;
  'Prof. Dr. R\"oschenthaler, Gerd Volker'
;  Institut of Inorganic and Physical Chemistry
   University of Bremen
   Leobener Str.
   D-28359 Bremen
   Germany
;

 
data_ak17 
  
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C12 H24 F6 N4 S2' 
_chemical_formula_weight          402.47 
  
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' 
 '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            orthorhombic 
_symmetry_space_group_name_H-M    Pbca 
  
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x+1/2, -y, z+1/2' 
 '-x, y+1/2, -z+1/2' 
 'x+1/2, -y+1/2, -z' 
 '-x, -y, -z' 
 'x-1/2, y, -z-1/2' 
 'x, -y-1/2, z-1/2' 
 '-x-1/2, y-1/2, z' 
  
_cell_length_a                    14.3400(10) 
_cell_length_b                    11.7810(10) 
_cell_length_c                    22.0320(10) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      3722.1(4) 
_cell_formula_units_Z             8 
_cell_measurement_temperature     173(2) 
_cell_measurement_reflns_used     82 
_cell_measurement_theta_min       2.840
_cell_measurement_theta_max       12.662
  
_exptl_crystal_description        blocks 
_exptl_crystal_colour             colorless 
_exptl_crystal_size_max           0.40 
_exptl_crystal_size_mid           0.30 
_exptl_crystal_size_min           0.30 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.436 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1680 
_exptl_absorpt_coefficient_mu     0.345 
_exptl_absorpt_correction_type    none 
_exptl_absorpt_correction_T_min   0.8744 
_exptl_absorpt_correction_T_max   0.9036 
_exptl_absorpt_process_details    ? 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       173(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'normal-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Siemens P4'
_diffrn_measurement_method        '2\q/\w scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          3 
_diffrn_standards_interval_count  197 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         'random variation +/-2.0' 
_diffrn_reflns_number             12961 
_diffrn_reflns_av_R_equivalents   0.0609 
_diffrn_reflns_av_sigmaI/netI     0.0409 
_diffrn_reflns_limit_h_min        -13 
_diffrn_reflns_limit_h_max        13 
_diffrn_reflns_limit_k_min        -11 
_diffrn_reflns_limit_k_max        11 
_diffrn_reflns_limit_l_min        -21 
_diffrn_reflns_limit_l_max        21 
_diffrn_reflns_theta_min          2.84 
_diffrn_reflns_theta_max          20.00 
_reflns_number_total              1730 
_reflns_number_gt                 1367 
_reflns_threshold_expression      >2sigma(I) 
  
_computing_data_collection        'Siemens XSCANS' 
_computing_cell_refinement        'Siemens XSCANS' 
_computing_data_reduction         'Siemens XSCANS' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'Siemens SHELXTL' 
_computing_publication_material   SHELXL-97 
  
_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^)+(0.0284P)^2^+6.2869P] 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     refU
_refine_ls_extinction_method      SHELXL 
_refine_ls_extinction_coef        0.0010(2) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' 
_refine_ls_number_reflns          1730 
_refine_ls_number_parameters      227 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0592 
_refine_ls_R_factor_gt            0.0416 
_refine_ls_wR_factor_ref          0.0933 
_refine_ls_wR_factor_gt           0.0854 
_refine_ls_goodness_of_fit_ref    1.039 
_refine_ls_restrained_S_all       1.039 
_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_symetry_multiplicity 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
C1 C 0.4256(3) 0.2705(4) 0.59681(18) 0.0219(11) Uani 1 1 d . . . 
N1 N 0.3820(2) 0.3284(3) 0.55408(15) 0.0259(9) Uani 1 1 d . . . 
C10 C 0.4202(3) 0.3483(4) 0.49253(18) 0.0373(13) Uani 1 1 d . . . 
H10A H 0.4878 0.3368 0.4931 0.044(3) Uiso 1 1 calc R . . 
H10B H 0.4063 0.4262 0.4799 0.044(3) Uiso 1 1 calc R . . 
H10C H 0.3916 0.2949 0.4639 0.044(3) Uiso 1 1 calc R . . 
C11 C 0.2901(3) 0.3809(4) 0.56394(19) 0.0338(12) Uani 1 1 d . . . 
H11A H 0.2694 0.3658 0.6055 0.044(3) Uiso 1 1 calc R . . 
H11B H 0.2451 0.3488 0.5352 0.044(3) Uiso 1 1 calc R . . 
H11C H 0.2948 0.4630 0.5576 0.044(3) Uiso 1 1 calc R . . 
N2 N 0.4924(2) 0.1967(3) 0.58928(14) 0.0254(9) Uani 1 1 d . . . 
C20 C 0.5104(3) 0.1357(4) 0.53226(19) 0.0371(12) Uani 1 1 d . . . 
H20A H 0.4542 0.1370 0.5070 0.044(3) Uiso 1 1 calc R . . 
H20B H 0.5274 0.0569 0.5413 0.044(3) Uiso 1 1 calc R . . 
H20C H 0.5618 0.1726 0.5105 0.044(3) Uiso 1 1 calc R . . 
C21 C 0.5544(3) 0.1628(4) 0.63899(19) 0.0343(12) Uani 1 1 d . . . 
H21A H 0.5430 0.2115 0.6743 0.044(3) Uiso 1 1 calc R . . 
H21B H 0.6194 0.1707 0.6260 0.044(3) Uiso 1 1 calc R . . 
H21C H 0.5420 0.0836 0.6499 0.044(3) Uiso 1 1 calc R . . 
C2 C 0.3936(3) 0.2895(4) 0.66136(18) 0.0243(11) Uani 1 1 d . . . 
N3 N 0.3477(2) 0.2049(3) 0.68661(14) 0.0264(9) Uani 1 1 d . . . 
C30 C 0.3395(3) 0.1855(4) 0.75216(19) 0.0397(13) Uani 1 1 d . . . 
H30A H 0.3897 0.2257 0.7733 0.044(3) Uiso 1 1 calc R . . 
H30B H 0.3441 0.1041 0.7606 0.044(3) Uiso 1 1 calc R . . 
H30C H 0.2791 0.2139 0.7664 0.044(3) Uiso 1 1 calc R . . 
C31 C 0.3015(3) 0.1167(3) 0.64982(19) 0.0322(12) Uani 1 1 d . . . 
H31A H 0.3085 0.1349 0.6067 0.044(3) Uiso 1 1 calc R . . 
H31B H 0.2351 0.1138 0.6602 0.044(3) Uiso 1 1 calc R . . 
H31C H 0.3302 0.0429 0.6582 0.044(3) Uiso 1 1 calc R . . 
N4 N 0.4149(2) 0.3872(3) 0.68670(15) 0.0264(9) Uani 1 1 d . . . 
C40 C 0.3695(3) 0.4329(4) 0.74108(19) 0.0373(13) Uani 1 1 d . . . 
H40A H 0.3061 0.4025 0.7442 0.044(3) Uiso 1 1 calc R . . 
H40B H 0.3669 0.5159 0.7383 0.044(3) Uiso 1 1 calc R . . 
H40C H 0.4053 0.4111 0.7771 0.044(3) Uiso 1 1 calc R . . 
C41 C 0.4889(3) 0.4598(4) 0.6616(2) 0.0376(12) Uani 1 1 d . . . 
H41A H 0.5182 0.4214 0.6270 0.044(3) Uiso 1 1 calc R . . 
H41B H 0.5359 0.4743 0.6929 0.044(3) Uiso 1 1 calc R . . 
H41C H 0.4619 0.5319 0.6481 0.044(3) Uiso 1 1 calc R . . 
S1 S 0.61087(9) 0.18688(11) 0.28890(5) 0.0418(4) Uani 1 1 d . . . 
C3 C 0.5635(3) 0.1998(4) 0.3603(2) 0.0342(12) Uani 1 1 d . . . 
F1 F 0.60635(18) 0.2736(2) 0.39821(11) 0.0488(8) Uani 1 1 d . . . 
F2 F 0.5630(2) 0.1019(2) 0.39346(12) 0.0603(9) Uani 1 1 d . . . 
F3 F 0.47382(18) 0.2346(3) 0.36224(12) 0.0640(9) Uani 1 1 d . . . 
S2 S 0.69150(10) 0.35741(10) 0.53104(6) 0.0491(4) Uani 1 1 d . . . 
C4 C 0.7437(4) 0.4157(4) 0.5925(2) 0.0463(14) Uani 1 1 d . . . 
F4 F 0.8347(2) 0.4339(3) 0.58957(19) 0.1085(14) Uani 1 1 d . . . 
F5 F 0.7119(3) 0.5161(3) 0.61105(17) 0.1108(15) Uani 1 1 d . . . 
F6 F 0.7369(3) 0.3553(4) 0.64362(17) 0.146(2) 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 
C1 0.019(3) 0.023(3) 0.024(3) -0.002(2) -0.004(2) -0.004(2) 
N1 0.027(2) 0.029(2) 0.021(2) -0.0015(18) 0.0005(18) 0.0022(18) 
C10 0.043(3) 0.045(3) 0.024(3) 0.007(2) 0.007(2) 0.005(3) 
C11 0.033(3) 0.040(3) 0.029(3) 0.001(2) 0.000(2) 0.006(2) 
N2 0.028(2) 0.028(2) 0.021(2) -0.0024(18) -0.0012(18) 0.005(2) 
C20 0.048(3) 0.032(3) 0.031(3) -0.009(2) 0.002(2) 0.008(2) 
C21 0.034(3) 0.036(3) 0.033(3) -0.003(2) -0.004(2) 0.008(2) 
C2 0.026(3) 0.024(3) 0.023(3) -0.003(2) -0.001(2) 0.004(2) 
N3 0.031(2) 0.027(2) 0.022(2) -0.0014(19) 0.0015(18) -0.0001(19) 
C30 0.050(3) 0.044(3) 0.026(3) 0.009(2) -0.001(2) 0.001(2) 
C31 0.035(3) 0.026(3) 0.036(3) 0.000(2) 0.001(2) -0.006(2) 
N4 0.029(2) 0.028(2) 0.022(2) -0.0050(19) -0.0007(18) 0.0046(19) 
C40 0.045(3) 0.038(3) 0.029(3) -0.010(2) -0.005(3) 0.009(2) 
C41 0.041(3) 0.032(3) 0.039(3) 0.002(2) -0.009(2) -0.006(3) 
S1 0.0375(8) 0.0618(9) 0.0261(7) -0.0002(6) 0.0032(6) -0.0021(7) 
C3 0.032(3) 0.040(3) 0.031(3) 0.000(3) -0.004(2) -0.001(3) 
F1 0.0528(18) 0.0574(19) 0.0363(15) -0.0127(14) -0.0057(14) -0.0115(15) 
F2 0.096(2) 0.0404(18) 0.0444(17) 0.0108(15) 0.0239(16) -0.0009(16) 
F3 0.0296(18) 0.119(3) 0.0434(17) -0.0138(18) -0.0009(14) 0.0150(17) 
S2 0.0649(10) 0.0377(8) 0.0447(8) 0.0028(7) -0.0128(7) -0.0059(7) 
C4 0.040(4) 0.043(3) 0.056(4) 0.014(3) -0.011(3) -0.006(3) 
F4 0.043(2) 0.129(3) 0.154(4) -0.050(3) -0.005(2) -0.025(2) 
F5 0.114(3) 0.107(3) 0.112(3) -0.066(3) -0.050(3) 0.042(3) 
F6 0.198(5) 0.169(4) 0.072(3) 0.054(3) -0.074(3) -0.094(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 
C1 N2 1.305(5) . ? 
C1 N1 1.320(5) . ? 
C1 C2 1.511(6) . ? 
N1 C11 1.471(5) . ? 
N1 C10 1.481(5) . ? 
N2 C21 1.465(5) . ? 
N2 C20 1.470(5) . ? 
C2 N4 1.315(5) . ? 
C2 N3 1.318(5) . ? 
N3 C30 1.467(5) . ? 
N3 C31 1.474(5) . ? 
N4 C40 1.466(5) . ? 
N4 C41 1.471(5) . ? 
S1 C3 1.720(5) . ? 
C3 F3 1.351(5) . ? 
C3 F1 1.353(5) . ? 
C3 F2 1.366(5) . ? 
S2 C4 1.692(5) . ? 
C4 F4 1.325(6) . ? 
C4 F5 1.333(6) . ? 
C4 F6 1.336(5) . ? 
  
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 
N2 C1 N1 127.0(4) . . ? 
N2 C1 C2 116.2(4) . . ? 
N1 C1 C2 116.8(4) . . ? 
C1 N1 C11 122.4(3) . . ? 
C1 N1 C10 124.1(3) . . ? 
C11 N1 C10 113.5(3) . . ? 
C1 N2 C21 122.1(3) . . ? 
C1 N2 C20 124.3(3) . . ? 
C21 N2 C20 113.5(3) . . ? 
N4 C2 N3 126.8(4) . . ? 
N4 C2 C1 117.3(4) . . ? 
N3 C2 C1 115.9(4) . . ? 
C2 N3 C30 125.0(4) . . ? 
C2 N3 C31 121.7(3) . . ? 
C30 N3 C31 113.3(3) . . ? 
C2 N4 C40 124.5(4) . . ? 
C2 N4 C41 121.1(3) . . ? 
C40 N4 C41 114.4(3) . . ? 
F3 C3 F1 102.5(4) . . ? 
F3 C3 F2 103.6(4) . . ? 
F1 C3 F2 102.4(3) . . ? 
F3 C3 S1 115.6(3) . . ? 
F1 C3 S1 116.2(3) . . ? 
F2 C3 S1 114.6(3) . . ? 
F4 C4 F5 102.0(4) . . ? 
F4 C4 F6 101.5(4) . . ? 
F5 C4 F6 100.8(5) . . ? 
F4 C4 S2 117.6(4) . . ? 
F5 C4 S2 117.1(4) . . ? 
F6 C4 S2 115.3(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 
N2 C1 N1 C11 160.1(4) . . . . ? 
C2 C1 N1 C11 -18.5(5) . . . . ? 
N2 C1 N1 C10 -20.7(6) . . . . ? 
C2 C1 N1 C10 160.7(4) . . . . ? 
N1 C1 N2 C21 161.4(4) . . . . ? 
C2 C1 N2 C21 -20.0(6) . . . . ? 
N1 C1 N2 C20 -21.8(6) . . . . ? 
C2 C1 N2 C20 156.8(4) . . . . ? 
N2 C1 C2 N4 109.3(4) . . . . ? 
N1 C1 C2 N4 -71.9(5) . . . . ? 
N2 C1 C2 N3 -70.0(5) . . . . ? 
N1 C1 C2 N3 108.8(4) . . . . ? 
N4 C2 N3 C30 -22.4(6) . . . . ? 
C1 C2 N3 C30 156.8(4) . . . . ? 
N4 C2 N3 C31 159.8(4) . . . . ? 
C1 C2 N3 C31 -21.0(5) . . . . ? 
N3 C2 N4 C40 -18.2(6) . . . . ? 
C1 C2 N4 C40 162.5(4) . . . . ? 
N3 C2 N4 C41 161.3(4) . . . . ? 
C1 C2 N4 C41 -17.9(5) . . . . ? 
  
_diffrn_measured_fraction_theta_max    0.998 
_diffrn_reflns_theta_full              20.00 
_diffrn_measured_fraction_theta_full   0.998 
_refine_diff_density_max    0.406 
_refine_diff_density_min   -0.265 
_refine_diff_density_rms    0.044 

#===END