# Electronic Supplementary Material for PCCP # This journal is © The Owner Societies 2009 data_global _journal_coden_Cambridge 1326 loop_ _publ_author_name 'Iwona Olejniczak' _publ_contact_author_name 'Iwona Olejniczak' _publ_contact_author_email YWY@IFMPAN.POZNAN.PL _publ_section_title ; Infrared and Raman spectra of beta''-(BEDT-TTF)2RCH2SO3 (R = SF5, CF3): dimerization related to hydrogen bonding ; # Attachment 'ETCF3CH2SO3150K.cif' data_ETCF3CH2SO3150K _database_code_depnum_ccdc_archive 'CCDC 713195' _chemical_name_systematic ; bis(ethylenedithio)tetrathiafulvalene trifluorofluoromethylsulfonate ; _chemical_name_common ; bis(ethylenedithio)tetrathiafulvalene trifluorofluoromethylsulfonate ; _chemical_melting_point ? _chemical_formula_moiety '2(C10 H8 S8), C2 H2 F3 O3 S' _chemical_formula_sum 'C22 H18 F3 O3 S17' _chemical_formula_weight 932.38 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' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7924(4) _cell_length_b 11.6205(6) _cell_length_c 17.1222(8) _cell_angle_alpha 77.617(2) _cell_angle_beta 87.597(2) _cell_angle_gamma 77.705(2) _cell_volume 1669.51(14) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1959 _cell_measurement_theta_min 2.724 _cell_measurement_theta_max 28.186 _exptl_crystal_description plate _exptl_crystal_colour black _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.52 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.855 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 946 _exptl_absorpt_coefficient_mu 1.145 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.498 _exptl_absorpt_correction_T_max 0.756 _exptl_absorpt_process_details ; (Sheldrick, 2001) ; _exptl_special_details ; The data collection nominally covered over a hemisphere of reciprocal space by a combination of five sets of exposures; each set had a different \f angle for the crystal and each exposure covered 0.3\% in \w. The crystal-to-detector distance was 5.025 cm. ; _diffrn_ambient_temperature 150(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 'Siemens SMART CCD' _diffrn_measurement_method 'area detector \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 16010 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0299 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 28.28 _diffrn_measured_fraction_theta_max 0.934 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.987 _reflns_number_total 7748 _reflns_number_gt 6813 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Siemens, 1997-1998)' _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_reduction 'SAINT (Bruker, 2001)' _computing_structure_solution 'SHELXTL (Sheldrick, 2001)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2001)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2001)' _computing_publication_material ; SHELXTL (Sheldrick, 2001), PLATON (Spek, 2003) ; _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^)+(0.0381P)^2^+0.9150P] 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 SHELXL _refine_ls_extinction_coef 0.0141(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7748 _refine_ls_number_parameters 431 _refine_ls_number_restraints 20 _refine_ls_R_factor_all 0.0338 _refine_ls_R_factor_gt 0.0294 _refine_ls_wR_factor_ref 0.0821 _refine_ls_wR_factor_gt 0.0783 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.707 _refine_diff_density_min -0.426 _refine_diff_density_rms 0.082 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 0.24059(5) 0.45785(3) 0.37157(2) 0.01975(9) Uani 1 1 d . . . S2 S 0.44249(5) 0.22657(3) 0.36225(2) 0.02039(9) Uani 1 1 d . . . S3 S 0.11950(5) 0.33918(3) 0.54488(2) 0.02057(9) Uani 1 1 d . . . S4 S 0.33122(4) 0.11028(3) 0.53838(2) 0.01984(9) Uani 1 1 d . . . S5 S 0.28934(5) 0.57965(3) 0.20598(2) 0.02308(10) Uani 1 1 d . . . S6 S 0.53749(5) 0.30058(3) 0.19476(2) 0.02266(10) Uani 1 1 d . . . S7 S -0.02039(5) 0.25093(4) 0.69969(2) 0.02430(10) Uani 1 1 d . . . S8 S 0.24570(5) -0.02089(4) 0.69404(2) 0.02441(10) Uani 1 1 d . . . C1 C 0.30901(17) 0.30875(13) 0.41692(9) 0.0177(3) Uani 1 1 d . . . C2 C 0.25875(17) 0.25855(13) 0.49144(9) 0.0176(3) Uani 1 1 d . . . C3 C 0.33286(18) 0.44808(13) 0.27988(9) 0.0181(3) Uani 1 1 d . A . C4 C 0.42791(18) 0.33985(13) 0.27593(9) 0.0186(3) Uani 1 1 d . A . C5 C 0.11402(18) 0.21936(13) 0.62545(9) 0.0187(3) Uani 1 1 d . . . C6 C 0.21453(18) 0.11354(13) 0.62308(9) 0.0182(3) Uani 1 1 d . . . C7A C 0.3707(4) 0.5267(3) 0.1180(2) 0.0261(3) Uiso 0.517(2) 1 d PD A 1 H7AA H 0.3032 0.4781 0.1013 0.031 Uiso 0.517(2) 1 calc PR A 1 H7AB H 0.3737 0.5967 0.0737 0.031 Uiso 0.517(2) 1 calc PR A 1 C8A C 0.5335(4) 0.4512(3) 0.1341(2) 0.0261(3) Uiso 0.517(2) 1 d PD A 1 H8AA H 0.5939 0.4934 0.1618 0.031 Uiso 0.517(2) 1 calc PR A 1 H8AB H 0.5852 0.4435 0.0824 0.031 Uiso 0.517(2) 1 calc PR A 1 C7B C 0.4363(5) 0.5433(3) 0.1312(2) 0.0261(3) Uiso 0.483(2) 1 d PD A 2 H7BA H 0.4099 0.6029 0.0804 0.031 Uiso 0.483(2) 1 calc PR A 2 H7BB H 0.5386 0.5505 0.1494 0.031 Uiso 0.483(2) 1 calc PR A 2 C8B C 0.4494(4) 0.4196(3) 0.1160(2) 0.0261(3) Uiso 0.483(2) 1 d PD A 2 H8BA H 0.5107 0.4134 0.0667 0.031 Uiso 0.483(2) 1 calc PR A 2 H8BB H 0.3438 0.4085 0.1062 0.031 Uiso 0.483(2) 1 calc PR A 2 C9 C 0.0607(2) 0.13219(15) 0.78304(10) 0.0249(3) Uani 1 1 d . . . H9A H 0.1603 0.1472 0.7993 0.030 Uiso 1 1 calc R . . H9B H -0.0115 0.1345 0.8289 0.030 Uiso 1 1 calc R . . C10 C 0.08963(19) 0.00778(15) 0.76401(10) 0.0237(3) Uani 1 1 d . . . H10A H -0.0074 -0.0031 0.7419 0.028 Uiso 1 1 calc R . . H10B H 0.1137 -0.0530 0.8145 0.028 Uiso 1 1 calc R . . S11 S 0.45399(5) 0.71502(3) 0.36328(2) 0.02205(9) Uani 1 1 d . . . S12 S 0.25442(5) 0.95140(3) 0.37093(2) 0.02120(9) Uani 1 1 d . . . S13 S 0.33209(5) 0.60381(3) 0.54047(2) 0.02115(9) Uani 1 1 d . . . S14 S 0.11801(5) 0.83866(3) 0.54021(2) 0.02224(9) Uani 1 1 d . . . S15 S 0.55479(5) 0.78807(4) 0.19634(3) 0.02622(10) Uani 1 1 d . . . S16 S 0.31611(5) 1.07032(4) 0.20610(2) 0.02479(10) Uani 1 1 d . . . S17 S 0.24432(6) 0.48478(4) 0.69929(3) 0.03260(11) Uani 1 1 d . . . S18 S -0.02596(5) 0.75680(4) 0.69572(3) 0.02577(10) Uani 1 1 d . . . C11 C 0.31495(17) 0.79942(14) 0.41666(9) 0.0184(3) Uani 1 1 d . . . C12 C 0.26027(18) 0.75238(13) 0.48910(9) 0.0185(3) Uani 1 1 d . . . C13 C 0.44060(18) 0.82937(14) 0.27591(9) 0.0202(3) Uani 1 1 d . . . C14 C 0.34889(18) 0.93739(14) 0.27961(9) 0.0200(3) Uani 1 1 d . . . C15 C 0.21151(19) 0.61509(14) 0.62413(9) 0.0203(3) Uani 1 1 d . . . C16 C 0.11124(19) 0.72140(14) 0.62298(9) 0.0206(3) Uani 1 1 d . . . C17 C 0.4913(2) 0.91687(15) 0.11587(10) 0.0258(3) Uani 1 1 d . . . H17A H 0.5656 0.9124 0.0710 0.031 Uiso 1 1 calc R . . H17B H 0.3884 0.9130 0.0964 0.031 Uiso 1 1 calc R . . C18 C 0.47876(19) 1.03680(15) 0.13993(10) 0.0243(3) Uani 1 1 d . . . H18A H 0.4670 1.1017 0.0912 0.029 Uiso 1 1 calc R . . H18B H 0.5765 1.0360 0.1669 0.029 Uiso 1 1 calc R . . C19 C 0.0928(2) 0.51878(16) 0.77022(11) 0.0301(4) Uani 1 1 d . . . H19A H -0.0042 0.5019 0.7523 0.036 Uiso 1 1 calc R . . H19B H 0.1221 0.4637 0.8225 0.036 Uiso 1 1 calc R . . C20 C 0.0595(2) 0.64695(17) 0.78223(10) 0.0304(4) Uani 1 1 d . . . H20A H 0.1580 0.6665 0.7959 0.036 Uiso 1 1 calc R . . H20B H -0.0120 0.6529 0.8281 0.036 Uiso 1 1 calc R . . S21 S -0.17772(4) 0.17060(3) 1.01223(2) 0.02197(10) Uani 1 1 d . . . O1 O -0.19262(14) 0.19717(11) 0.92604(7) 0.0281(3) Uani 1 1 d . . . O2 O -0.19820(15) 0.05014(11) 1.04987(7) 0.0313(3) Uani 1 1 d . . . O3 O -0.26819(17) 0.26355(13) 1.04966(9) 0.0421(3) Uani 1 1 d . . . C21 C 0.0225(2) 0.16583(15) 1.03274(10) 0.0274(3) Uani 1 1 d D B . H21A H 0.0355 0.1527 1.0914 0.033 Uiso 1 1 calc R . . H21B H 0.0872 0.0950 1.0153 0.033 Uiso 1 1 calc R . . C22 C 0.0849(2) 0.27405(16) 0.99462(11) 0.0315(4) Uani 1 1 d D . . F1A F -0.0045(6) 0.3791(4) 0.9979(7) 0.0567(15) Uani 0.70(3) 1 d PD B 1 F2A F 0.1146(9) 0.2775(5) 0.9177(3) 0.0455(11) Uani 0.70(3) 1 d PD B 1 F3A F 0.2194(10) 0.2748(8) 1.0286(5) 0.0621(16) Uani 0.70(3) 1 d PD B 1 F1B F 0.064(3) 0.311(3) 0.9163(8) 0.069(5) Uani 0.30(3) 1 d PD B 2 F2B F 0.2401(13) 0.2553(17) 1.0057(15) 0.061(4) Uani 0.30(3) 1 d PD B 2 F3B F 0.016(2) 0.3683(14) 1.0272(14) 0.082(4) Uani 0.30(3) 1 d PD B 2 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 0.02507(19) 0.01706(18) 0.01471(18) -0.00246(14) 0.00478(14) -0.00090(14) S2 0.02302(19) 0.01838(18) 0.01621(18) -0.00163(14) 0.00543(14) 0.00043(14) S3 0.0246(2) 0.01724(18) 0.01692(18) -0.00244(14) 0.00581(14) -0.00007(15) S4 0.02200(19) 0.01849(18) 0.01526(18) -0.00133(14) 0.00498(14) 0.00090(14) S5 0.0305(2) 0.01657(18) 0.01826(19) -0.00072(14) 0.00962(15) -0.00117(15) S6 0.0296(2) 0.01717(18) 0.01906(19) -0.00336(14) 0.01059(15) -0.00257(15) S7 0.0279(2) 0.02180(19) 0.0212(2) -0.00557(15) 0.01113(16) -0.00196(16) S8 0.0316(2) 0.01915(19) 0.01779(19) 0.00052(15) 0.00707(15) -0.00073(16) C1 0.0192(7) 0.0178(7) 0.0151(7) -0.0030(5) 0.0020(5) -0.0030(6) C2 0.0198(7) 0.0173(7) 0.0143(7) -0.0019(5) 0.0023(5) -0.0026(6) C3 0.0228(7) 0.0169(7) 0.0140(7) -0.0022(5) 0.0041(5) -0.0049(6) C4 0.0226(7) 0.0177(7) 0.0154(7) -0.0034(6) 0.0057(6) -0.0051(6) C5 0.0217(7) 0.0186(7) 0.0154(7) -0.0042(6) 0.0039(5) -0.0034(6) C6 0.0218(7) 0.0185(7) 0.0136(7) -0.0028(5) 0.0027(5) -0.0035(6) C9 0.0271(8) 0.0307(8) 0.0170(7) -0.0069(6) 0.0037(6) -0.0052(7) C10 0.0240(8) 0.0271(8) 0.0181(7) 0.0005(6) 0.0053(6) -0.0072(6) S11 0.0244(2) 0.01967(18) 0.01826(19) -0.00093(14) 0.00399(14) -0.00011(15) S12 0.0259(2) 0.01868(18) 0.01625(18) -0.00114(14) 0.00245(14) -0.00154(15) S13 0.02337(19) 0.01849(19) 0.01787(19) -0.00145(14) 0.00461(14) 0.00050(15) S14 0.0266(2) 0.01759(18) 0.01877(19) -0.00190(15) 0.00374(15) 0.00098(15) S15 0.0301(2) 0.0230(2) 0.0227(2) -0.00226(16) 0.01070(16) -0.00372(16) S16 0.0253(2) 0.02193(19) 0.0218(2) 0.00292(15) 0.00657(15) -0.00191(15) S17 0.0492(3) 0.0181(2) 0.0231(2) 0.00156(16) 0.01263(19) 0.00085(18) S18 0.0293(2) 0.02092(19) 0.0259(2) -0.00633(16) 0.01193(16) -0.00357(16) C11 0.0185(7) 0.0183(7) 0.0171(7) -0.0021(6) 0.0008(5) -0.0027(6) C12 0.0206(7) 0.0182(7) 0.0154(7) -0.0025(6) 0.0017(5) -0.0029(6) C13 0.0204(7) 0.0220(7) 0.0176(7) -0.0020(6) 0.0042(6) -0.0062(6) C14 0.0209(7) 0.0211(7) 0.0171(7) -0.0011(6) 0.0025(6) -0.0060(6) C15 0.0259(8) 0.0172(7) 0.0171(7) -0.0026(6) 0.0039(6) -0.0048(6) C16 0.0254(8) 0.0177(7) 0.0192(7) -0.0051(6) 0.0057(6) -0.0051(6) C17 0.0307(9) 0.0264(8) 0.0195(8) -0.0034(6) 0.0018(6) -0.0060(7) C18 0.0264(8) 0.0244(8) 0.0203(8) -0.0009(6) 0.0053(6) -0.0060(6) C19 0.0294(9) 0.0293(9) 0.0262(9) 0.0051(7) 0.0066(7) -0.0067(7) C20 0.0296(9) 0.0387(10) 0.0212(8) -0.0085(7) 0.0033(7) -0.0016(7) S21 0.02250(19) 0.02296(19) 0.01797(19) -0.00345(14) 0.00482(14) -0.00112(15) O1 0.0298(6) 0.0335(6) 0.0180(6) -0.0017(5) -0.0005(5) -0.0036(5) O2 0.0316(6) 0.0298(6) 0.0295(7) 0.0029(5) 0.0036(5) -0.0098(5) O3 0.0447(8) 0.0385(8) 0.0398(8) -0.0163(6) 0.0168(6) 0.0036(6) C21 0.0308(9) 0.0259(8) 0.0232(8) 0.0011(6) -0.0028(7) -0.0069(7) C22 0.0400(10) 0.0294(9) 0.0266(9) -0.0031(7) -0.0015(7) -0.0129(8) F1A 0.070(2) 0.0244(11) 0.078(4) -0.0175(17) 0.022(2) -0.0123(12) F2A 0.064(3) 0.048(2) 0.0283(15) -0.0027(13) 0.0136(14) -0.0285(16) F3A 0.067(3) 0.065(3) 0.059(3) 0.0097(19) -0.0232(19) -0.043(2) F1B 0.092(11) 0.091(11) 0.030(4) 0.021(5) -0.013(5) -0.066(9) F2B 0.031(3) 0.069(5) 0.087(9) -0.011(6) -0.006(4) -0.027(3) F3B 0.161(11) 0.047(5) 0.061(7) -0.034(5) 0.044(6) -0.054(6) _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 C1 1.7277(15) . ? S1 C3 1.7512(15) . ? S2 C1 1.7261(15) . ? S2 C4 1.7445(15) . ? S3 C2 1.7318(15) . ? S3 C5 1.7445(16) . ? S4 C2 1.7326(15) . ? S4 C6 1.7434(15) . ? S5 C3 1.7454(15) . ? S5 C7A 1.811(3) . ? S5 C7B 1.830(4) . ? S6 C4 1.7437(15) . ? S6 C8B 1.779(4) . ? S6 C8A 1.827(3) . ? S7 C5 1.7426(15) . ? S7 C9 1.8086(17) . ? S8 C6 1.7387(15) . ? S8 C10 1.8079(16) . ? C1 C2 1.381(2) . ? C3 C4 1.367(2) . ? C5 C6 1.360(2) . ? C7A C8A 1.513(4) . ? C7A H7AA 0.9900 . ? C7A H7AB 0.9900 . ? C8A H8AA 0.9900 . ? C8A H8AB 0.9900 . ? C7B C8B 1.496(5) . ? C7B H7BA 0.9900 . ? C7B H7BB 0.9900 . ? C8B H8BA 0.9900 . ? C8B H8BB 0.9900 . ? C9 C10 1.516(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? S11 C11 1.7526(16) . ? S11 C13 1.7644(16) . ? S12 C11 1.7484(16) . ? S12 C14 1.7618(16) . ? S13 C12 1.7562(16) . ? S13 C15 1.7571(16) . ? S14 C16 1.7516(16) . ? S14 C12 1.7567(15) . ? S15 C13 1.7478(16) . ? S15 C17 1.8096(17) . ? S16 C14 1.7493(16) . ? S16 C18 1.8157(17) . ? S17 C15 1.7440(16) . ? S17 C19 1.8032(18) . ? S18 C16 1.7487(16) . ? S18 C20 1.8061(19) . ? C11 C12 1.356(2) . ? C13 C14 1.352(2) . ? C15 C16 1.353(2) . ? C17 C18 1.517(2) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.512(3) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? S21 O1 1.4471(12) . ? S21 O3 1.4485(13) . ? S21 O2 1.4553(12) . ? S21 C21 1.7969(18) . ? C21 C22 1.490(2) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 F1A 1.315(4) . ? C22 F1B 1.326(11) . ? C22 F2A 1.326(5) . ? C22 F3A 1.342(6) . ? C22 F2B 1.350(11) . ? C22 F3B 1.352(10) . ? 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 C1 S1 C3 95.63(7) . . ? C1 S2 C4 95.75(7) . . ? C2 S3 C5 95.72(7) . . ? C2 S4 C6 95.75(7) . . ? C3 S5 C7A 101.57(12) . . ? C3 S5 C7B 100.52(13) . . ? C4 S6 C8B 100.53(13) . . ? C4 S6 C8A 99.28(12) . . ? C5 S7 C9 100.45(7) . . ? C6 S8 C10 102.20(7) . . ? C2 C1 S2 122.36(12) . . ? C2 C1 S1 122.17(12) . . ? S2 C1 S1 115.46(9) . . ? C1 C2 S3 122.51(12) . . ? C1 C2 S4 122.32(12) . . ? S3 C2 S4 115.18(8) . . ? C4 C3 S5 129.15(12) . . ? C4 C3 S1 116.21(11) . . ? S5 C3 S1 114.64(8) . . ? C3 C4 S6 127.89(12) . . ? C3 C4 S2 116.55(11) . . ? S6 C4 S2 115.56(9) . . ? C6 C5 S7 127.96(12) . . ? C6 C5 S3 116.63(12) . . ? S7 C5 S3 115.41(9) . . ? C5 C6 S8 128.92(12) . . ? C5 C6 S4 116.65(12) . . ? S8 C6 S4 114.43(8) . . ? C8A C7A S5 111.2(2) . . ? C8A C7A H7AA 109.4 . . ? S5 C7A H7AA 109.4 . . ? C8A C7A H7AB 109.4 . . ? S5 C7A H7AB 109.4 . . ? H7AA C7A H7AB 108.0 . . ? C7A C8A S6 113.4(2) . . ? C7A C8A H8AA 108.9 . . ? S6 C8A H8AA 108.9 . . ? C7A C8A H8AB 108.9 . . ? S6 C8A H8AB 108.9 . . ? H8AA C8A H8AB 107.7 . . ? C8B C7B S5 113.3(3) . . ? C8B C7B H7BA 108.9 . . ? S5 C7B H7BA 108.9 . . ? C8B C7B H7BB 108.9 . . ? S5 C7B H7BB 108.9 . . ? H7BA C7B H7BB 107.7 . . ? C7B C8B S6 114.8(3) . . ? C7B C8B H8BA 108.6 . . ? S6 C8B H8BA 108.6 . . ? C7B C8B H8BB 108.6 . . ? S6 C8B H8BB 108.6 . . ? H8BA C8B H8BB 107.5 . . ? C10 C9 S7 113.11(11) . . ? C10 C9 H9A 109.0 . . ? S7 C9 H9A 109.0 . . ? C10 C9 H9B 109.0 . . ? S7 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C9 C10 S8 114.65(11) . . ? C9 C10 H10A 108.6 . . ? S8 C10 H10A 108.6 . . ? C9 C10 H10B 108.6 . . ? S8 C10 H10B 108.6 . . ? H10A C10 H10B 107.6 . . ? C11 S11 C13 95.06(7) . . ? C11 S12 C14 95.00(7) . . ? C12 S13 C15 94.92(7) . . ? C16 S14 C12 95.06(7) . . ? C13 S15 C17 101.93(8) . . ? C14 S16 C18 100.42(8) . . ? C15 S17 C19 102.70(8) . . ? C16 S18 C20 100.23(8) . . ? C12 C11 S12 121.81(12) . . ? C12 C11 S11 123.12(13) . . ? S12 C11 S11 115.05(9) . . ? C11 C12 S13 122.71(12) . . ? C11 C12 S14 122.01(12) . . ? S13 C12 S14 115.22(8) . . ? C14 C13 S15 128.52(12) . . ? C14 C13 S11 116.76(12) . . ? S15 C13 S11 114.68(9) . . ? C13 C14 S16 128.52(12) . . ? C13 C14 S12 117.26(12) . . ? S16 C14 S12 114.16(9) . . ? C16 C15 S17 129.18(13) . . ? C16 C15 S13 117.33(12) . . ? S17 C15 S13 113.46(9) . . ? C15 C16 S18 127.35(13) . . ? C15 C16 S14 117.38(12) . . ? S18 C16 S14 115.27(9) . . ? C18 C17 S15 113.53(12) . . ? C18 C17 H17A 108.9 . . ? S15 C17 H17A 108.9 . . ? C18 C17 H17B 108.9 . . ? S15 C17 H17B 108.9 . . ? H17A C17 H17B 107.7 . . ? C17 C18 S16 113.02(11) . . ? C17 C18 H18A 109.0 . . ? S16 C18 H18A 109.0 . . ? C17 C18 H18B 109.0 . . ? S16 C18 H18B 109.0 . . ? H18A C18 H18B 107.8 . . ? C20 C19 S17 115.18(12) . . ? C20 C19 H19A 108.5 . . ? S17 C19 H19A 108.5 . . ? C20 C19 H19B 108.5 . . ? S17 C19 H19B 108.5 . . ? H19A C19 H19B 107.5 . . ? C19 C20 S18 113.60(12) . . ? C19 C20 H20A 108.8 . . ? S18 C20 H20A 108.8 . . ? C19 C20 H20B 108.8 . . ? S18 C20 H20B 108.8 . . ? H20A C20 H20B 107.7 . . ? O1 S21 O3 113.75(8) . . ? O1 S21 O2 113.49(8) . . ? O3 S21 O2 113.17(8) . . ? O1 S21 C21 106.05(8) . . ? O3 S21 C21 105.87(9) . . ? O2 S21 C21 103.35(8) . . ? C22 C21 S21 116.49(12) . . ? C22 C21 H21A 108.2 . . ? S21 C21 H21A 108.2 . . ? C22 C21 H21B 108.2 . . ? S21 C21 H21B 108.2 . . ? H21A C21 H21B 107.3 . . ? F1A C22 F2A 105.6(4) . . ? F1A C22 F3A 104.6(4) . . ? F2A C22 F3A 106.5(4) . . ? F1B C22 F2B 105.2(9) . . ? F1B C22 F3B 106.0(9) . . ? F2B C22 F3B 108.0(9) . . ? F1A C22 C21 116.3(3) . . ? F1B C22 C21 116.1(8) . . ? F2A C22 C21 111.7(3) . . ? F3A C22 C21 111.5(3) . . ? F2B C22 C21 111.6(8) . . ? F3B C22 C21 109.6(7) . . ? 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 S2 C1 C2 173.17(14) . . . . ? C4 S2 C1 S1 -6.08(10) . . . . ? C3 S1 C1 C2 -172.94(14) . . . . ? C3 S1 C1 S2 6.31(10) . . . . ? S2 C1 C2 S3 -177.54(8) . . . . ? S1 C1 C2 S3 1.7(2) . . . . ? S2 C1 C2 S4 2.7(2) . . . . ? S1 C1 C2 S4 -178.09(8) . . . . ? C5 S3 C2 C1 177.83(14) . . . . ? C5 S3 C2 S4 -2.41(10) . . . . ? C6 S4 C2 C1 -178.65(14) . . . . ? C6 S4 C2 S3 1.59(10) . . . . ? C7A S5 C3 C4 10.9(2) . . . . ? C7B S5 C3 C4 -11.8(2) . . . . ? C7A S5 C3 S1 -169.02(14) . . . . ? C7B S5 C3 S1 168.24(14) . . . . ? C1 S1 C3 C4 -4.09(14) . . . . ? C1 S1 C3 S5 175.88(9) . . . . ? S5 C3 C4 S6 0.7(2) . . . . ? S1 C3 C4 S6 -179.34(9) . . . . ? S5 C3 C4 S2 -179.40(9) . . . . ? S1 C3 C4 S2 0.56(17) . . . . ? C8B S6 C4 C3 -15.74(19) . . . . ? C8A S6 C4 C3 16.26(19) . . . . ? C8B S6 C4 S2 164.35(14) . . . . ? C8A S6 C4 S2 -163.65(13) . . . . ? C1 S2 C4 C3 3.28(14) . . . . ? C1 S2 C4 S6 -176.80(9) . . . . ? C9 S7 C5 C6 20.70(17) . . . . ? C9 S7 C5 S3 -159.03(9) . . . . ? C2 S3 C5 C6 2.61(14) . . . . ? C2 S3 C5 S7 -177.63(9) . . . . ? S7 C5 C6 S8 -2.5(2) . . . . ? S3 C5 C6 S8 177.22(9) . . . . ? S7 C5 C6 S4 178.32(9) . . . . ? S3 C5 C6 S4 -1.96(18) . . . . ? C10 S8 C6 C5 8.87(17) . . . . ? C10 S8 C6 S4 -171.94(9) . . . . ? C2 S4 C6 C5 0.21(14) . . . . ? C2 S4 C6 S8 -179.08(9) . . . . ? C3 S5 C7A C8A -47.0(2) . . . . ? S5 C7A C8A S6 74.6(3) . . . . ? C4 S6 C8A C7A -53.9(2) . . . . ? C3 S5 C7B C8B 45.8(3) . . . . ? S5 C7B C8B S6 -71.9(3) . . . . ? C4 S6 C8B C7B 51.2(3) . . . . ? C5 S7 C9 C10 -52.97(13) . . . . ? S7 C9 C10 S8 69.40(14) . . . . ? C6 S8 C10 C9 -42.11(14) . . . . ? C14 S12 C11 C12 -172.45(14) . . . . ? C14 S12 C11 S11 9.20(10) . . . . ? C13 S11 C11 C12 172.54(14) . . . . ? C13 S11 C11 S12 -9.13(10) . . . . ? S12 C11 C12 S13 -174.00(8) . . . . ? S11 C11 C12 S13 4.2(2) . . . . ? S12 C11 C12 S14 3.1(2) . . . . ? S11 C11 C12 S14 -178.72(8) . . . . ? C15 S13 C12 C11 178.74(14) . . . . ? C15 S13 C12 S14 1.49(10) . . . . ? C16 S14 C12 C11 -179.86(14) . . . . ? C16 S14 C12 S13 -2.60(10) . . . . ? C17 S15 C13 C14 -9.94(17) . . . . ? C17 S15 C13 S11 172.44(9) . . . . ? C11 S11 C13 C14 5.36(14) . . . . ? C11 S11 C13 S15 -176.73(9) . . . . ? S15 C13 C14 S16 -0.3(2) . . . . ? S11 C13 C14 S16 177.25(9) . . . . ? S15 C13 C14 S12 -177.38(9) . . . . ? S11 C13 C14 S12 0.19(18) . . . . ? C18 S16 C14 C13 -16.71(17) . . . . ? C18 S16 C14 S12 160.42(9) . . . . ? C11 S12 C14 C13 -5.65(14) . . . . ? C11 S12 C14 S16 176.87(9) . . . . ? C19 S17 C15 C16 7.56(19) . . . . ? C19 S17 C15 S13 -174.37(9) . . . . ? C12 S13 C15 C16 0.70(15) . . . . ? C12 S13 C15 S17 -177.62(9) . . . . ? S17 C15 C16 S18 -4.3(3) . . . . ? S13 C15 C16 S18 177.72(9) . . . . ? S17 C15 C16 S14 175.30(10) . . . . ? S13 C15 C16 S14 -2.71(19) . . . . ? C20 S18 C16 C15 23.57(17) . . . . ? C20 S18 C16 S14 -156.02(10) . . . . ? C12 S14 C16 C15 3.17(14) . . . . ? C12 S14 C16 S18 -177.21(9) . . . . ? C13 S15 C17 C18 45.18(14) . . . . ? S15 C17 C18 S16 -71.27(14) . . . . ? C14 S16 C18 C17 51.58(13) . . . . ? C15 S17 C19 C20 -39.17(15) . . . . ? S17 C19 C20 S18 67.76(16) . . . . ? C16 S18 C20 C19 -54.29(14) . . . . ? O1 S21 C21 C22 54.58(15) . . . . ? O3 S21 C21 C22 -66.58(15) . . . . ? O2 S21 C21 C22 174.22(13) . . . . ? S21 C21 C22 F1A 44.7(6) . . . . ? S21 C21 C22 F1B -51.9(18) . . . . ? S21 C21 C22 F2A -76.6(4) . . . . ? S21 C21 C22 F3A 164.5(6) . . . . ? S21 C21 C22 F2B -172.3(12) . . . . ? S21 C21 C22 F3B 68.1(13) . . . . ? # Attachment 'ETCF3CH2SO3RT.cif' data_ETCF3CH2SO3RT _database_code_depnum_ccdc_archive 'CCDC 713196' _chemical_name_systematic ; bis(ethylenedithio)tetrathiafulvalene trifluorofluoromethylsulfonate ; _chemical_name_common ; bis(ethylenedithio)tetrathiafulvalene trifluorofluoromethylsulfonate ; _chemical_formula_moiety '2(C10 H8 S8), C2 H2 F3 O3 S' _chemical_formula_sum 'C22 H18 F3 O3 S17' _chemical_formula_weight 932.38 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' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8890(5) _cell_length_b 11.7375(6) _cell_length_c 17.2190(9) _cell_angle_alpha 77.299(2) _cell_angle_beta 86.942(2) _cell_angle_gamma 77.239(2) _cell_volume 1709.27(16) _cell_formula_units_Z 2 _cell_measurement_temperature 568(2) _cell_measurement_reflns_used 1764 _cell_measurement_theta_min 2.394 _cell_measurement_theta_max 28.138 _exptl_crystal_description plate _exptl_crystal_colour black _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.52 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.812 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 946 _exptl_absorpt_coefficient_mu 1.119 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.503 _exptl_absorpt_correction_T_max 0.760 _exptl_absorpt_process_details ; (Sheldrick, 2001) ; _exptl_special_details ; The data collection nominally covered over a hemisphere of reciprocal space by a combination of five sets of exposures; each set had a different \f angle for the crystal and each exposure covered 0.3\% in \w. The crystal-to-detector distance was 5.025 cm. ; _diffrn_ambient_temperature 298(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 'Siemens SMART CCD' _diffrn_measurement_method 'area detector \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 16451 _diffrn_reflns_av_R_equivalents 0.0282 _diffrn_reflns_av_sigmaI/netI 0.0340 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 28.29 _diffrn_measured_fraction_theta_max 0.933 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.987 _reflns_number_total 7926 _reflns_number_gt 6044 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Siemens, 1997-1998)' _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_reduction 'SAINT (Bruker, 2001)' _computing_structure_solution 'SHELXTL (Sheldrick, 2001)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2001)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2001)' _computing_publication_material ; SHELXTL (Sheldrick, 2001), PLATON (Spek, 2003) ; _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^)+(0.0548P)^2^+1.6214P] 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 SHELXL _refine_ls_extinction_coef 0.0489(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7926 _refine_ls_number_parameters 403 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0585 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1290 _refine_ls_wR_factor_gt 0.1162 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.633 _refine_diff_density_min -0.742 _refine_diff_density_rms 0.082 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 0.24408(8) 0.45401(6) 0.37235(4) 0.03968(17) Uani 1 1 d . . . S2 S 0.44110(8) 0.22374(6) 0.36220(4) 0.03999(17) Uani 1 1 d . . . S3 S 0.12109(8) 0.33756(6) 0.54421(4) 0.04247(17) Uani 1 1 d . . . S4 S 0.32963(8) 0.10963(6) 0.53890(4) 0.03897(16) Uani 1 1 d . . . S5 S 0.29462(9) 0.57556(6) 0.20782(4) 0.04567(19) Uani 1 1 d . . . S6 S 0.53852(9) 0.29839(6) 0.19580(4) 0.04448(19) Uani 1 1 d . . . S7 S -0.01868(9) 0.25298(7) 0.69881(4) 0.0523(2) Uani 1 1 d . . . S8 S 0.24459(10) -0.01737(6) 0.69541(4) 0.0497(2) Uani 1 1 d . . . C1 C 0.3102(3) 0.3059(2) 0.41734(13) 0.0331(5) Uani 1 1 d . . . C2 C 0.2598(3) 0.2567(2) 0.49183(13) 0.0331(5) Uani 1 1 d . . . C3 C 0.3366(3) 0.4451(2) 0.28138(14) 0.0333(5) Uani 1 1 d . A . C4 C 0.4294(3) 0.3373(2) 0.27696(14) 0.0335(5) Uani 1 1 d . A . C5 C 0.1153(3) 0.2203(2) 0.62539(14) 0.0357(5) Uani 1 1 d . . . C6 C 0.2144(3) 0.1145(2) 0.62329(13) 0.0333(5) Uani 1 1 d . . . C7A C 0.4385(6) 0.5411(4) 0.1332(3) 0.0469(7) Uiso 0.625(4) 1 d P A 1 H7A1 H 0.4129 0.6001 0.0841 0.056 Uiso 0.625(4) 1 calc PR A 1 H7A2 H 0.5379 0.5470 0.1507 0.056 Uiso 0.625(4) 1 calc PR A 1 C8A C 0.4512(6) 0.4171(4) 0.1170(3) 0.0469(7) Uiso 0.625(4) 1 d P A 1 H8A1 H 0.5112 0.4114 0.0687 0.056 Uiso 0.625(4) 1 calc PR A 1 H8A2 H 0.3487 0.4070 0.1077 0.056 Uiso 0.625(4) 1 calc PR A 1 C7B C 0.3727(10) 0.5220(7) 0.1196(5) 0.0469(7) Uiso 0.375(4) 1 d P A 2 H7B1 H 0.3045 0.4769 0.1041 0.056 Uiso 0.375(4) 1 calc PR A 2 H7B2 H 0.3757 0.5902 0.0763 0.056 Uiso 0.375(4) 1 calc PR A 2 C8B C 0.5270(9) 0.4467(7) 0.1314(5) 0.0469(7) Uiso 0.375(4) 1 d P A 2 H8B1 H 0.5910 0.4882 0.1540 0.056 Uiso 0.375(4) 1 calc PR A 2 H8B2 H 0.5702 0.4367 0.0798 0.056 Uiso 0.375(4) 1 calc PR A 2 C9 C 0.0575(4) 0.1348(3) 0.78168(17) 0.0522(7) Uani 1 1 d . . . H9A H 0.1527 0.1492 0.7986 0.063 Uiso 1 1 calc R . . H9B H -0.0152 0.1374 0.8256 0.063 Uiso 1 1 calc R . . C10 C 0.0889(3) 0.0122(3) 0.76416(17) 0.0493(7) Uani 1 1 d . . . H10A H -0.0042 0.0007 0.7429 0.059 Uiso 1 1 calc R . . H10B H 0.1119 -0.0461 0.8138 0.059 Uiso 1 1 calc R . . S11 S 0.45383(8) 0.71719(6) 0.36389(4) 0.04300(17) Uani 1 1 d . . . S12 S 0.25461(8) 0.95163(6) 0.37159(4) 0.04172(17) Uani 1 1 d . . . S13 S 0.33202(8) 0.60600(6) 0.54008(4) 0.04271(17) Uani 1 1 d . . . S14 S 0.12217(9) 0.83962(6) 0.54156(4) 0.04542(18) Uani 1 1 d . . . S15 S 0.55317(9) 0.78989(6) 0.19745(4) 0.0498(2) Uani 1 1 d . . . S16 S 0.31347(9) 1.06882(6) 0.20680(4) 0.04842(19) Uani 1 1 d . . . S17 S 0.23998(12) 0.48629(7) 0.69699(5) 0.0661(3) Uani 1 1 d . . . S18 S -0.02088(10) 0.75725(7) 0.69622(5) 0.0545(2) Uani 1 1 d . . . C11 C 0.3159(3) 0.8008(2) 0.41736(14) 0.0346(5) Uani 1 1 d . . . C12 C 0.2625(3) 0.7540(2) 0.48980(14) 0.0348(5) Uani 1 1 d . . . C13 C 0.4400(3) 0.8306(2) 0.27703(15) 0.0371(5) Uani 1 1 d . . . C14 C 0.3483(3) 0.9379(2) 0.28068(14) 0.0362(5) Uani 1 1 d . . . C15 C 0.2119(3) 0.6165(2) 0.62294(15) 0.0384(5) Uani 1 1 d . . . C16 C 0.1145(3) 0.7223(2) 0.62334(15) 0.0377(5) Uani 1 1 d . . . C17 C 0.4907(4) 0.9173(3) 0.11774(18) 0.0571(8) Uani 1 1 d . . . H17A H 0.5650 0.9135 0.0745 0.068 Uiso 1 1 calc R . . H17B H 0.3929 0.9117 0.0980 0.068 Uiso 1 1 calc R . . C18 C 0.4717(4) 1.0354(3) 0.13934(18) 0.0549(8) Uani 1 1 d . . . H18A H 0.4563 1.0972 0.0910 0.066 Uiso 1 1 calc R . . H18B H 0.5665 1.0384 0.1635 0.066 Uiso 1 1 calc R . . C19 C 0.0974(5) 0.5224(3) 0.7690(2) 0.0730(11) Uani 1 1 d . . . H19A H 0.0036 0.5022 0.7552 0.088 Uiso 1 1 calc R . . H19B H 0.1313 0.4708 0.8199 0.088 Uiso 1 1 calc R . . C20 C 0.0578(5) 0.6448(4) 0.7800(2) 0.0708(10) Uani 1 1 d . . . H20A H 0.1501 0.6643 0.7964 0.085 Uiso 1 1 calc R . . H20B H -0.0159 0.6483 0.8235 0.085 Uiso 1 1 calc R . . S21 S -0.17955(8) 0.17351(6) 1.01092(4) 0.04478(19) Uani 1 1 d . . . O1 O -0.1965(3) 0.1995(2) 0.92577(12) 0.0586(6) Uani 1 1 d . . . O2 O -0.1986(3) 0.0548(2) 1.04932(14) 0.0657(6) Uani 1 1 d . . . O3 O -0.2670(3) 0.2664(3) 1.04787(18) 0.0927(9) Uani 1 1 d . . . C21 C 0.0188(4) 0.1687(3) 1.02772(19) 0.0559(8) Uani 1 1 d . . . H21A H 0.0347 0.1512 1.0848 0.067 Uiso 1 1 calc R . . H21B H 0.0806 0.1021 1.0076 0.067 Uiso 1 1 calc R . . C22 C 0.0794(5) 0.2755(3) 0.9928(2) 0.0663(9) Uani 1 1 d . . . F1 F 0.0048(5) 0.3728(3) 1.0107(3) 0.1749(19) Uani 1 1 d . . . F2 F 0.0830(5) 0.2993(3) 0.91705(15) 0.1551(16) Uani 1 1 d . . . F3 F 0.2197(4) 0.2689(3) 1.0146(3) 0.1700(18) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0507(4) 0.0339(3) 0.0271(3) -0.0035(2) 0.0102(3) 0.0009(3) S2 0.0465(4) 0.0346(3) 0.0302(3) -0.0016(2) 0.0115(3) 0.0015(3) S3 0.0515(4) 0.0344(3) 0.0322(3) -0.0029(3) 0.0126(3) 0.0031(3) S4 0.0444(4) 0.0356(3) 0.0279(3) -0.0019(2) 0.0102(2) 0.0030(3) S5 0.0601(4) 0.0333(3) 0.0338(3) -0.0001(3) 0.0174(3) -0.0006(3) S6 0.0580(4) 0.0337(3) 0.0360(3) -0.0057(3) 0.0211(3) -0.0043(3) S7 0.0610(5) 0.0454(4) 0.0430(4) -0.0098(3) 0.0264(3) -0.0018(3) S8 0.0669(5) 0.0380(4) 0.0333(3) 0.0024(3) 0.0142(3) -0.0016(3) C1 0.0365(12) 0.0357(12) 0.0240(11) -0.0046(9) 0.0049(9) -0.0039(10) C2 0.0360(12) 0.0351(12) 0.0243(11) -0.0043(9) 0.0046(9) -0.0026(10) C3 0.0417(13) 0.0306(11) 0.0256(11) -0.0040(9) 0.0097(9) -0.0077(10) C4 0.0397(13) 0.0319(11) 0.0278(11) -0.0057(9) 0.0103(9) -0.0086(10) C5 0.0420(13) 0.0350(12) 0.0279(11) -0.0074(10) 0.0106(10) -0.0057(10) C6 0.0398(13) 0.0336(12) 0.0241(11) -0.0044(9) 0.0050(9) -0.0058(10) C9 0.0556(17) 0.069(2) 0.0326(14) -0.0156(13) 0.0114(12) -0.0128(15) C10 0.0499(16) 0.0585(17) 0.0345(14) 0.0031(12) 0.0090(12) -0.0161(14) S11 0.0488(4) 0.0382(3) 0.0337(3) -0.0022(3) 0.0087(3) 0.0004(3) S12 0.0520(4) 0.0363(3) 0.0300(3) -0.0022(3) 0.0065(3) -0.0013(3) S13 0.0487(4) 0.0359(3) 0.0341(3) -0.0020(3) 0.0105(3) 0.0027(3) S14 0.0572(4) 0.0337(3) 0.0358(3) -0.0026(3) 0.0110(3) 0.0026(3) S15 0.0598(4) 0.0431(4) 0.0422(4) -0.0071(3) 0.0212(3) -0.0088(3) S16 0.0524(4) 0.0420(4) 0.0400(4) 0.0047(3) 0.0135(3) -0.0039(3) S17 0.0984(7) 0.0366(4) 0.0463(4) 0.0046(3) 0.0262(4) 0.0017(4) S18 0.0634(5) 0.0434(4) 0.0501(4) -0.0100(3) 0.0267(4) -0.0036(3) C11 0.0359(12) 0.0370(12) 0.0279(11) -0.0043(10) 0.0021(9) -0.0049(10) C12 0.0384(12) 0.0352(12) 0.0274(11) -0.0047(9) 0.0033(9) -0.0037(10) C13 0.0392(13) 0.0399(13) 0.0314(12) -0.0052(10) 0.0088(10) -0.0116(11) C14 0.0391(13) 0.0387(13) 0.0295(12) -0.0031(10) 0.0057(10) -0.0115(10) C15 0.0474(14) 0.0335(12) 0.0312(12) -0.0043(10) 0.0073(10) -0.0067(11) C16 0.0450(14) 0.0334(12) 0.0321(12) -0.0066(10) 0.0103(10) -0.0061(10) C17 0.069(2) 0.0619(19) 0.0383(15) -0.0088(14) 0.0074(14) -0.0131(16) C18 0.0628(19) 0.0535(17) 0.0413(16) -0.0002(13) 0.0146(13) -0.0107(14) C19 0.079(2) 0.064(2) 0.057(2) 0.0139(17) 0.0219(18) -0.0063(18) C20 0.077(2) 0.086(3) 0.0411(17) -0.0142(17) 0.0103(16) -0.002(2) S21 0.0462(4) 0.0471(4) 0.0329(3) -0.0044(3) 0.0099(3) 0.0005(3) O1 0.0584(13) 0.0756(15) 0.0349(11) -0.0003(10) -0.0044(9) -0.0105(11) O2 0.0637(14) 0.0611(14) 0.0634(14) 0.0103(11) 0.0071(11) -0.0200(11) O3 0.097(2) 0.0828(18) 0.088(2) -0.0347(15) 0.0403(16) 0.0089(15) C21 0.064(2) 0.0527(17) 0.0459(17) 0.0028(13) -0.0069(14) -0.0137(15) C22 0.083(3) 0.063(2) 0.056(2) -0.0033(16) -0.0052(18) -0.0297(19) F1 0.215(4) 0.0727(19) 0.261(5) -0.074(2) 0.097(4) -0.066(2) F2 0.247(4) 0.193(3) 0.0587(16) 0.0181(18) 0.004(2) -0.165(3) F3 0.136(3) 0.152(3) 0.222(4) 0.043(3) -0.074(3) -0.097(3) _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 C1 1.724(2) . ? S1 C3 1.743(2) . ? S2 C1 1.724(2) . ? S2 C4 1.743(2) . ? S3 C2 1.725(2) . ? S3 C5 1.740(2) . ? S4 C2 1.729(2) . ? S4 C6 1.737(2) . ? S5 C3 1.742(2) . ? S5 C7A 1.809(5) . ? S5 C7B 1.816(8) . ? S6 C4 1.744(2) . ? S6 C8A 1.786(5) . ? S6 C8B 1.832(8) . ? S7 C5 1.736(2) . ? S7 C9 1.799(3) . ? S8 C6 1.737(2) . ? S8 C10 1.797(3) . ? C1 C2 1.381(3) . ? C3 C4 1.364(3) . ? C5 C6 1.361(3) . ? C7A C8A 1.521(7) . ? C7A H7A1 0.9700 . ? C7A H7A2 0.9700 . ? C8A H8A1 0.9700 . ? C8A H8A2 0.9700 . ? C7B C8B 1.455(11) . ? C7B H7B1 0.9700 . ? C7B H7B2 0.9700 . ? C8B H8B1 0.9700 . ? C8B H8B2 0.9700 . ? C9 C10 1.497(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? S11 C11 1.749(2) . ? S11 C13 1.760(3) . ? S12 C11 1.749(3) . ? S12 C14 1.756(2) . ? S13 C15 1.745(3) . ? S13 C12 1.753(2) . ? S14 C16 1.750(3) . ? S14 C12 1.755(2) . ? S15 C13 1.746(2) . ? S15 C17 1.800(3) . ? S16 C14 1.746(3) . ? S16 C18 1.807(3) . ? S17 C15 1.741(3) . ? S17 C19 1.775(4) . ? S18 C16 1.743(2) . ? S18 C20 1.782(4) . ? C11 C12 1.354(3) . ? C13 C14 1.352(3) . ? C15 C16 1.349(3) . ? C17 C18 1.486(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.454(5) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? S21 O1 1.439(2) . ? S21 O3 1.440(2) . ? S21 O2 1.447(2) . ? S21 C21 1.789(3) . ? C21 C22 1.469(5) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 F2 1.272(4) . ? C22 F1 1.279(5) . ? C22 F3 1.302(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 C1 S1 C3 95.94(11) . . ? C1 S2 C4 95.71(11) . . ? C2 S3 C5 95.86(11) . . ? C2 S4 C6 95.80(11) . . ? C3 S5 C7A 101.26(17) . . ? C3 S5 C7B 101.6(3) . . ? C4 S6 C8A 100.74(17) . . ? C4 S6 C8B 100.2(3) . . ? C5 S7 C9 100.65(13) . . ? C6 S8 C10 102.42(13) . . ? C2 C1 S2 122.67(19) . . ? C2 C1 S1 122.04(19) . . ? S2 C1 S1 115.28(13) . . ? C1 C2 S3 122.31(19) . . ? C1 C2 S4 122.50(19) . . ? S3 C2 S4 115.19(13) . . ? C4 C3 S5 128.93(18) . . ? C4 C3 S1 116.12(18) . . ? S5 C3 S1 114.94(13) . . ? C3 C4 S2 116.65(17) . . ? C3 C4 S6 127.87(18) . . ? S2 C4 S6 115.48(13) . . ? C6 C5 S7 128.05(19) . . ? C6 C5 S3 116.44(18) . . ? S7 C5 S3 115.50(14) . . ? C5 C6 S4 116.68(18) . . ? C5 C6 S8 128.45(19) . . ? S4 C6 S8 114.86(13) . . ? C8A C7A S5 113.1(4) . . ? C8A C7A H7A1 109.0 . . ? S5 C7A H7A1 109.0 . . ? C8A C7A H7A2 109.0 . . ? S5 C7A H7A2 109.0 . . ? H7A1 C7A H7A2 107.8 . . ? C7A C8A S6 113.9(4) . . ? C7A C8A H8A1 108.8 . . ? S6 C8A H8A1 108.8 . . ? C7A C8A H8A2 108.8 . . ? S6 C8A H8A2 108.8 . . ? H8A1 C8A H8A2 107.7 . . ? C8B C7B S5 113.1(6) . . ? C8B C7B H7B1 109.0 . . ? S5 C7B H7B1 109.0 . . ? C8B C7B H7B2 109.0 . . ? S5 C7B H7B2 109.0 . . ? H7B1 C7B H7B2 107.8 . . ? C7B C8B S6 115.5(6) . . ? C7B C8B H8B1 108.4 . . ? S6 C8B H8B1 108.4 . . ? C7B C8B H8B2 108.4 . . ? S6 C8B H8B2 108.4 . . ? H8B1 C8B H8B2 107.5 . . ? C10 C9 S7 114.2(2) . . ? C10 C9 H9A 108.7 . . ? S7 C9 H9A 108.7 . . ? C10 C9 H9B 108.7 . . ? S7 C9 H9B 108.7 . . ? H9A C9 H9B 107.6 . . ? C9 C10 S8 115.1(2) . . ? C9 C10 H10A 108.5 . . ? S8 C10 H10A 108.5 . . ? C9 C10 H10B 108.5 . . ? S8 C10 H10B 108.5 . . ? H10A C10 H10B 107.5 . . ? C11 S11 C13 95.00(12) . . ? C11 S12 C14 95.01(12) . . ? C15 S13 C12 94.95(12) . . ? C16 S14 C12 94.94(11) . . ? C13 S15 C17 102.11(14) . . ? C14 S16 C18 100.69(13) . . ? C15 S17 C19 103.11(14) . . ? C16 S18 C20 100.42(15) . . ? C12 C11 S12 121.9(2) . . ? C12 C11 S11 123.0(2) . . ? S12 C11 S11 115.05(13) . . ? C11 C12 S13 122.8(2) . . ? C11 C12 S14 122.0(2) . . ? S13 C12 S14 115.14(13) . . ? C14 C13 S15 128.4(2) . . ? C14 C13 S11 116.92(19) . . ? S15 C13 S11 114.69(14) . . ? C13 C14 S16 128.43(19) . . ? C13 C14 S12 117.18(19) . . ? S16 C14 S12 114.36(14) . . ? C16 C15 S17 128.3(2) . . ? C16 C15 S13 117.70(19) . . ? S17 C15 S13 113.94(14) . . ? C15 C16 S18 127.7(2) . . ? C15 C16 S14 117.20(19) . . ? S18 C16 S14 115.13(14) . . ? C18 C17 S15 115.1(2) . . ? C18 C17 H17A 108.5 . . ? S15 C17 H17A 108.5 . . ? C18 C17 H17B 108.5 . . ? S15 C17 H17B 108.5 . . ? H17A C17 H17B 107.5 . . ? C17 C18 S16 114.6(2) . . ? C17 C18 H18A 108.6 . . ? S16 C18 H18A 108.6 . . ? C17 C18 H18B 108.6 . . ? S16 C18 H18B 108.6 . . ? H18A C18 H18B 107.6 . . ? C20 C19 S17 118.4(3) . . ? C20 C19 H19A 107.7 . . ? S17 C19 H19A 107.7 . . ? C20 C19 H19B 107.7 . . ? S17 C19 H19B 107.7 . . ? H19A C19 H19B 107.1 . . ? C19 C20 S18 116.7(3) . . ? C19 C20 H20A 108.1 . . ? S18 C20 H20A 108.1 . . ? C19 C20 H20B 108.1 . . ? S18 C20 H20B 108.1 . . ? H20A C20 H20B 107.3 . . ? O1 S21 O3 113.45(16) . . ? O1 S21 O2 113.56(15) . . ? O3 S21 O2 113.69(16) . . ? O1 S21 C21 105.51(14) . . ? O3 S21 C21 105.86(18) . . ? O2 S21 C21 103.55(14) . . ? C22 C21 S21 117.8(2) . . ? C22 C21 H21A 107.9 . . ? S21 C21 H21A 107.9 . . ? C22 C21 H21B 107.9 . . ? S21 C21 H21B 107.9 . . ? H21A C21 H21B 107.2 . . ? F2 C22 F1 104.2(4) . . ? F2 C22 F3 105.2(4) . . ? F1 C22 F3 103.1(4) . . ? F2 C22 C21 114.0(3) . . ? F1 C22 C21 115.4(4) . . ? F3 C22 C21 113.7(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 S2 C1 C2 174.0(2) . . . . ? C4 S2 C1 S1 -5.16(17) . . . . ? C3 S1 C1 C2 -173.7(2) . . . . ? C3 S1 C1 S2 5.41(17) . . . . ? S2 C1 C2 S3 -176.40(14) . . . . ? S1 C1 C2 S3 2.7(3) . . . . ? S2 C1 C2 S4 3.0(3) . . . . ? S1 C1 C2 S4 -177.92(14) . . . . ? C5 S3 C2 C1 178.1(2) . . . . ? C5 S3 C2 S4 -1.32(17) . . . . ? C6 S4 C2 C1 -178.8(2) . . . . ? C6 S4 C2 S3 0.65(17) . . . . ? C7A S5 C3 C4 -12.5(3) . . . . ? C7B S5 C3 C4 11.4(4) . . . . ? C7A S5 C3 S1 168.6(2) . . . . ? C7B S5 C3 S1 -167.5(3) . . . . ? C1 S1 C3 C4 -3.6(2) . . . . ? C1 S1 C3 S5 175.47(15) . . . . ? S5 C3 C4 S2 -178.30(16) . . . . ? S1 C3 C4 S2 0.6(3) . . . . ? S5 C3 C4 S6 1.5(4) . . . . ? S1 C3 C4 S6 -179.63(15) . . . . ? C1 S2 C4 C3 2.7(2) . . . . ? C1 S2 C4 S6 -177.08(15) . . . . ? C8A S6 C4 C3 -16.7(3) . . . . ? C8B S6 C4 C3 12.3(4) . . . . ? C8A S6 C4 S2 163.1(2) . . . . ? C8B S6 C4 S2 -167.9(3) . . . . ? C9 S7 C5 C6 20.2(3) . . . . ? C9 S7 C5 S3 -160.55(17) . . . . ? C2 S3 C5 C6 1.7(2) . . . . ? C2 S3 C5 S7 -177.56(16) . . . . ? S7 C5 C6 S4 177.61(16) . . . . ? S3 C5 C6 S4 -1.6(3) . . . . ? S7 C5 C6 S8 -3.8(4) . . . . ? S3 C5 C6 S8 176.98(15) . . . . ? C2 S4 C6 C5 0.6(2) . . . . ? C2 S4 C6 S8 -178.21(15) . . . . ? C10 S8 C6 C5 10.2(3) . . . . ? C10 S8 C6 S4 -171.16(16) . . . . ? C3 S5 C7A C8A 46.2(4) . . . . ? C7B S5 C7A C8A -47.0(7) . . . . ? S5 C7A C8A S6 -71.7(5) . . . . ? C4 S6 C8A C7A 51.2(4) . . . . ? C3 S5 C7B C8B -46.7(7) . . . . ? S5 C7B C8B S6 71.0(8) . . . . ? C4 S6 C8B C7B -49.2(7) . . . . ? C5 S7 C9 C10 -51.6(2) . . . . ? S7 C9 C10 S8 68.2(3) . . . . ? C6 S8 C10 C9 -42.1(3) . . . . ? C14 S12 C11 C12 -172.6(2) . . . . ? C14 S12 C11 S11 8.99(17) . . . . ? C13 S11 C11 C12 172.7(2) . . . . ? C13 S11 C11 S12 -8.88(17) . . . . ? S12 C11 C12 S13 -175.33(14) . . . . ? S11 C11 C12 S13 3.0(3) . . . . ? S12 C11 C12 S14 2.5(3) . . . . ? S11 C11 C12 S14 -179.18(14) . . . . ? C15 S13 C12 C11 180.0(2) . . . . ? C15 S13 C12 S14 1.98(17) . . . . ? C16 S14 C12 C11 179.3(2) . . . . ? C16 S14 C12 S13 -2.64(17) . . . . ? C17 S15 C13 C14 -9.6(3) . . . . ? C17 S15 C13 S11 172.60(16) . . . . ? C11 S11 C13 C14 5.2(2) . . . . ? C11 S11 C13 S15 -176.73(15) . . . . ? S15 C13 C14 S16 0.4(4) . . . . ? S11 C13 C14 S16 178.23(16) . . . . ? S15 C13 C14 S12 -177.51(16) . . . . ? S11 C13 C14 S12 0.3(3) . . . . ? C18 S16 C14 C13 -16.4(3) . . . . ? C18 S16 C14 S12 161.65(16) . . . . ? C11 S12 C14 C13 -5.6(2) . . . . ? C11 S12 C14 S16 176.18(15) . . . . ? C19 S17 C15 C16 5.0(3) . . . . ? C19 S17 C15 S13 -177.2(2) . . . . ? C12 S13 C15 C16 -0.2(3) . . . . ? C12 S13 C15 S17 -178.30(16) . . . . ? S17 C15 C16 S18 -4.1(4) . . . . ? S13 C15 C16 S18 178.17(16) . . . . ? S17 C15 C16 S14 176.12(17) . . . . ? S13 C15 C16 S14 -1.6(3) . . . . ? C20 S18 C16 C15 22.4(3) . . . . ? C20 S18 C16 S14 -157.79(19) . . . . ? C12 S14 C16 C15 2.6(2) . . . . ? C12 S14 C16 S18 -177.27(16) . . . . ? C13 S15 C17 C18 43.2(3) . . . . ? S15 C17 C18 S16 -68.5(3) . . . . ? C14 S16 C18 C17 49.6(3) . . . . ? C15 S17 C19 C20 -33.9(4) . . . . ? S17 C19 C20 S18 61.7(4) . . . . ? C16 S18 C20 C19 -50.4(3) . . . . ? O1 S21 C21 C22 57.8(3) . . . . ? O3 S21 C21 C22 -62.7(3) . . . . ? O2 S21 C21 C22 177.4(3) . . . . ? S21 C21 C22 F2 -66.0(5) . . . . ? S21 C21 C22 F1 54.5(5) . . . . ? S21 C21 C22 F3 173.4(3) . . . . ? # End