# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 182/1393 data_6HSN2 _publ_requested_journal 'test' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 6-hexylsulfonyl-2-napthol ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H20 O3 S' _chemical_formula_weight 292.38 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' '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 Cc 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' _cell_length_a 5.6190(2) _cell_length_b 15.8672(6) _cell_length_c 17.1890(7) _cell_angle_alpha 90.00 _cell_angle_beta 96.581(2) _cell_angle_gamma 90.00 _cell_volume 1522.44(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.276 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.217 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.9167 _exptl_absorpt_correction_T_max 0.9869 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4774 _diffrn_reflns_av_R_equivalents 0.0486 _diffrn_reflns_av_sigmaI/netI 0.0791 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 28.24 _reflns_number_total 2387 _reflns_number_gt 1810 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0673P)^2^+0.1274P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0061(13) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.05(12) _refine_ls_number_reflns 2387 _refine_ls_number_parameters 197 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0829 _refine_ls_R_factor_gt 0.0565 _refine_ls_wR_factor_ref 0.1334 _refine_ls_wR_factor_gt 0.1211 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _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 0.54545(14) 0.05022(6) 0.09982(6) 0.0276(3) Uani 1 1 d . . . C1 C 0.3756(8) 0.1096(3) 0.1615(2) 0.0320(10) Uani 1 1 d . . . H1A H 0.3675 0.1668 0.1450 0.066(13) Uiso 1 1 calc R . . H1B H 0.2170 0.0881 0.1583 0.066(13) Uiso 1 1 calc R . . C2 C 0.4944(8) 0.1040(3) 0.2456(2) 0.0289(9) Uani 1 1 d . . . H2A H 0.4833 0.0478 0.2638 0.038(9) Uiso 1 1 calc R . . H2B H 0.6594 0.1176 0.2469 0.038(9) Uiso 1 1 calc R . . C3 C 0.3796(8) 0.1631(3) 0.3003(2) 0.0294(9) Uani 1 1 d . . . H3A H 0.2175 0.1470 0.3022 0.026(8) Uiso 1 1 calc R . . H3B H 0.3806 0.2189 0.2803 0.026(8) Uiso 1 1 calc R . . C4 C 0.5118(9) 0.1613(3) 0.3828(2) 0.0304(10) Uani 1 1 d . . . H4A H 0.5003 0.1063 0.4039 0.041(10) Uiso 1 1 calc R . . H4B H 0.6766 0.1728 0.3801 0.041(10) Uiso 1 1 calc R . . C5 C 0.4154(9) 0.2244(3) 0.4378(2) 0.0334(10) Uani 1 1 d . . . H5A H 0.2510 0.2126 0.4411 0.042(9) Uiso 1 1 calc R . . H5B H 0.4256 0.2794 0.4167 0.042(9) Uiso 1 1 calc R . . C6 C 0.5502(11) 0.2228(3) 0.5201(3) 0.0504(13) Uani 1 1 d . . . H6A H 0.5261 0.1699 0.5439 0.062(10) Uiso 1 1 calc R . . H6B H 0.4921 0.2666 0.5506 0.062(10) Uiso 1 1 calc R . . H6C H 0.7164 0.2309 0.5171 0.062(10) Uiso 1 1 calc R . . C7 C 0.3851(7) 0.0534(3) 0.0059(2) 0.0271(9) Uani 1 1 d . . . C8 C 0.4717(8) 0.1021(3) -0.0506(2) 0.0285(10) Uani 1 1 d . . . H8 H 0.6164 0.1328 -0.0387 0.054(16) Uiso 1 1 calc R . . C9 C 0.3464(7) 0.1065(3) -0.1262(2) 0.0264(9) Uani 1 1 d . . . C10 C 0.4276(9) 0.1568(3) -0.1862(2) 0.0333(10) Uani 1 1 d . . . H10 H 0.5741 0.1868 -0.1758 0.057(16) Uiso 1 1 calc R . . C11 C 0.2994(8) 0.1630(3) -0.2584(2) 0.0332(10) Uani 1 1 d . . . H11 H 0.3546 0.1981 -0.2973 0.037(13) Uiso 1 1 calc R . . C12 C 0.0853(8) 0.1171(3) -0.2748(2) 0.0305(10) Uani 1 1 d . . . C13 C 0.0014(7) 0.0670(3) -0.2195(2) 0.0304(9) Uani 1 1 d . . . H13 H -0.1436 0.0365 -0.2318 0.038(13) Uiso 1 1 calc R . . C14 C 0.1294(7) 0.0600(3) -0.1436(2) 0.0250(9) Uani 1 1 d . . . C15 C 0.0484(8) 0.0102(3) -0.0838(2) 0.0314(10) Uani 1 1 d . . . H15 H -0.0959 -0.0210 -0.0946 0.026(11) Uiso 1 1 calc R . . C16 C 0.1727(8) 0.0057(3) -0.0106(2) 0.0300(9) Uani 1 1 d . . . H16 H 0.1171 -0.0290 0.0286 0.029(11) Uiso 1 1 calc R . . O1 O 0.7745(5) 0.09111(19) 0.09753(17) 0.0360(8) Uani 1 1 d . . . O2 O 0.5476(6) -0.03624(17) 0.12716(17) 0.0348(7) Uani 1 1 d . . . O3 O -0.0335(6) 0.1280(2) -0.34808(18) 0.0447(9) Uani 1 1 d . . . H3 H -0.1714 0.0962 -0.3530 0.10(2) 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 0.0230(5) 0.0391(5) 0.0200(4) -0.0003(5) 0.0001(3) 0.0018(5) C1 0.029(2) 0.045(3) 0.021(2) -0.0011(18) -0.0013(16) 0.007(2) C2 0.027(2) 0.036(2) 0.023(2) 0.0009(18) 0.0005(17) 0.0057(19) C3 0.029(2) 0.035(2) 0.024(2) 0.0007(17) 0.0019(17) 0.0046(18) C4 0.035(3) 0.033(2) 0.023(2) 0.0005(17) 0.0021(18) 0.0018(19) C5 0.042(3) 0.032(2) 0.025(2) -0.0010(18) -0.0025(18) 0.001(2) C6 0.070(4) 0.046(3) 0.033(3) -0.005(2) -0.008(2) 0.005(3) C7 0.023(2) 0.035(2) 0.0237(19) -0.0073(17) 0.0025(16) -0.0005(18) C8 0.024(2) 0.038(2) 0.023(2) -0.0066(17) 0.0024(17) -0.0054(19) C9 0.023(2) 0.034(2) 0.021(2) -0.0041(16) -0.0003(16) -0.0015(17) C10 0.032(2) 0.044(3) 0.024(2) -0.0008(19) 0.0034(18) -0.011(2) C11 0.030(2) 0.042(3) 0.026(2) 0.0020(19) -0.0020(18) -0.009(2) C12 0.030(2) 0.038(2) 0.022(2) -0.0040(18) -0.0059(16) 0.0003(19) C13 0.024(2) 0.039(2) 0.027(2) -0.0043(18) -0.0044(16) -0.0046(18) C14 0.022(2) 0.030(2) 0.0219(19) -0.0076(16) 0.0012(16) 0.0001(16) C15 0.026(2) 0.040(2) 0.028(2) -0.0048(19) -0.0001(18) -0.0046(19) C16 0.024(2) 0.039(2) 0.028(2) -0.0004(18) 0.0049(17) -0.0036(18) O1 0.0223(16) 0.059(2) 0.0259(15) 0.0000(14) -0.0007(12) -0.0065(14) O2 0.0361(18) 0.0349(16) 0.0315(16) -0.0011(13) -0.0044(14) 0.0075(15) O3 0.0397(19) 0.061(2) 0.0292(17) 0.0083(15) -0.0150(14) -0.0141(17) _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 O1 1.446(3) . ? S1 O2 1.450(3) . ? S1 C7 1.756(4) . ? S1 C1 1.777(4) . ? C1 C2 1.524(5) . ? C2 C3 1.522(5) . ? C3 C4 1.525(5) . ? C4 C5 1.519(6) . ? C5 C6 1.526(6) . ? C7 C8 1.373(6) . ? C7 C16 1.415(6) . ? C8 C9 1.407(5) . ? C9 C10 1.420(6) . ? C9 C14 1.427(5) . ? C10 C11 1.365(6) . ? C11 C12 1.407(6) . ? C12 C13 1.365(6) . ? C12 O3 1.367(5) . ? C13 C14 1.419(5) . ? C14 C15 1.413(6) . ? C15 C16 1.369(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 O1 S1 O2 117.33(18) . . ? O1 S1 C7 109.04(17) . . ? O2 S1 C7 108.04(18) . . ? O1 S1 C1 108.6(2) . . ? O2 S1 C1 107.08(19) . . ? C7 S1 C1 106.2(2) . . ? C2 C1 S1 109.2(3) . . ? C3 C2 C1 112.3(3) . . ? C2 C3 C4 111.5(3) . . ? C5 C4 C3 113.3(4) . . ? C4 C5 C6 113.0(4) . . ? C8 C7 C16 121.2(4) . . ? C8 C7 S1 118.7(3) . . ? C16 C7 S1 120.1(3) . . ? C7 C8 C9 120.1(4) . . ? C8 C9 C10 122.0(4) . . ? C8 C9 C14 119.6(3) . . ? C10 C9 C14 118.4(4) . . ? C11 C10 C9 121.4(4) . . ? C10 C11 C12 119.7(4) . . ? C13 C12 O3 123.0(4) . . ? C13 C12 C11 121.2(4) . . ? O3 C12 C11 115.8(4) . . ? C12 C13 C14 120.4(4) . . ? C15 C14 C13 122.7(4) . . ? C15 C14 C9 118.4(4) . . ? C13 C14 C9 118.9(3) . . ? C16 C15 C14 121.6(4) . . ? C15 C16 C7 119.1(4) . . ? _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 28.24 _diffrn_measured_fraction_theta_full 0.956 _refine_diff_density_max 0.707 _refine_diff_density_min -0.486 _refine_diff_density_rms 0.065 #===END data_6FHSN2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 6-perfluorohexylsulfonyl-2napthol ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H7 F13 O3 S' _chemical_formula_weight 526.28 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 33.2913(10) _cell_length_b 9.9469(2) _cell_length_c 11.4174(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.1870(10) _cell_angle_gamma 90.00 _cell_volume 3732.32(17) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.873 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2080 _exptl_absorpt_coefficient_mu 0.319 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.9378 _exptl_absorpt_correction_T_max 0.9579 _exptl_absorpt_process_details 'Blessing, ActaCryst. (1995) A51 33-38.' _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 SMART CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18775 _diffrn_reflns_av_R_equivalents 0.0860 _diffrn_reflns_av_sigmaI/netI 0.1015 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 39 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 0.62 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6536 _reflns_number_gt 3497 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1325P)^2^+11.6145P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6536 _refine_ls_number_parameters 597 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1764 _refine_ls_R_factor_gt 0.0971 _refine_ls_wR_factor_ref 0.2844 _refine_ls_wR_factor_gt 0.2320 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.002 _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 0.40785(6) 0.7095(2) 0.0451(2) 0.0441(6) Uani 1 1 d . . . F1 F 0.35373(16) 0.5451(5) -0.0527(6) 0.0823(19) Uani 1 1 d . . . F2 F 0.35433(14) 0.7379(6) -0.1468(4) 0.0645(15) Uani 1 1 d . . . F3 F 0.31730(15) 0.6507(6) 0.1109(4) 0.0696(16) Uani 1 1 d . . . F4 F 0.32626(14) 0.8523(5) 0.0524(4) 0.0593(14) Uani 1 1 d . . . F5 F 0.27741(16) 0.6110(6) -0.1358(5) 0.0784(18) Uani 1 1 d . . . F6 F 0.27489(15) 0.8290(6) -0.1393(4) 0.0690(16) Uani 1 1 d . . . F7 F 0.23845(15) 0.5963(6) 0.0430(5) 0.0793(18) Uani 1 1 d . . . F8 F 0.24521(16) 0.8061(6) 0.0812(5) 0.0735(16) Uani 1 1 d . . . F9 F 0.19571(17) 0.8741(6) -0.1053(6) 0.094(2) Uani 1 1 d . . . F10 F 0.19915(16) 0.6818(8) -0.1910(5) 0.092(2) Uani 1 1 d . . . F11 F 0.16253(17) 0.7356(7) 0.0717(5) 0.0822(18) Uani 1 1 d . . . F12 F 0.12899(17) 0.7397(9) -0.1022(6) 0.122(3) Uani 1 1 d . . . F13 F 0.15953(18) 0.5609(7) -0.0375(6) 0.095(2) Uani 1 1 d . . . O1 O 0.40523(18) 0.6800(6) 0.1664(5) 0.0584(16) Uani 1 1 d . . . O2 O 0.43271(17) 0.6302(5) -0.0192(6) 0.0607(17) Uani 1 1 d . . . O3 O 0.47991(16) 1.4485(5) -0.1235(4) 0.0392(13) Uani 1 1 d . . . H3 H 0.4691 1.5050 -0.0729 0.047 Uiso 1 1 calc R . . C1 C 0.3557(2) 0.6784(8) -0.0398(7) 0.045(2) Uani 1 1 d . . . C2 C 0.3192(2) 0.7264(7) 0.0156(7) 0.0411(19) Uani 1 1 d . . . C3 C 0.2781(2) 0.7206(8) -0.0699(7) 0.0428(19) Uani 1 1 d . . . C4 C 0.2406(2) 0.7162(8) -0.0073(7) 0.0401(19) Uani 1 1 d . . . C5 C 0.1994(3) 0.7411(10) -0.0853(8) 0.053(2) Uani 1 1 d . . . C6 C 0.1616(3) 0.6934(11) -0.0381(8) 0.062(3) Uani 1 1 d . . . C7 C 0.4191(2) 0.8784(7) 0.0280(7) 0.0376(19) Uani 1 1 d . . . C8 C 0.4391(2) 0.9155(7) -0.0631(6) 0.0318(17) Uani 1 1 d . . . H8 H 0.4453 0.8495 -0.1177 0.038 Uiso 1 1 calc R . . C9 C 0.4503(2) 1.0485(6) -0.0765(5) 0.0257(15) Uani 1 1 d . . . C10 C 0.4723(2) 1.0897(7) -0.1685(6) 0.0328(17) Uani 1 1 d . . . H10 H 0.4803 1.0248 -0.2213 0.039 Uiso 1 1 calc R . . C11 C 0.4818(2) 1.2223(7) -0.1804(6) 0.0335(17) Uani 1 1 d . . . H11 H 0.4962 1.2491 -0.2418 0.040 Uiso 1 1 calc R . . C12 C 0.4702(2) 1.3201(6) -0.1018(6) 0.0279(16) Uani 1 1 d . . . C13 C 0.4498(2) 1.2832(7) -0.0114(6) 0.0309(16) Uani 1 1 d . . . H13 H 0.4427 1.3496 0.0413 0.037 Uiso 1 1 calc R . . C14 C 0.4395(2) 1.1481(7) 0.0039(6) 0.0286(16) Uani 1 1 d . . . C15 C 0.4193(2) 1.1036(7) 0.0973(6) 0.0327(17) Uani 1 1 d . . . H15 H 0.4121 1.1681 0.1518 0.039 Uiso 1 1 calc R . . C16 C 0.4099(2) 0.9738(7) 0.1119(6) 0.0334(17) Uani 1 1 d . . . H16 H 0.3973 0.9467 0.1771 0.040 Uiso 1 1 calc R . . S1' S 0.09353(6) 0.30974(19) 0.62753(18) 0.0417(5) Uani 1 1 d . . . F1' F 0.15195(15) 0.4670(5) 0.6023(6) 0.0749(17) Uani 1 1 d . . . F2' F 0.14778(15) 0.2925(6) 0.4880(4) 0.0718(17) Uani 1 1 d . . . F3' F 0.18229(19) 0.3258(9) 0.7892(5) 0.112(3) Uani 1 1 d . . . F4' F 0.17269(16) 0.1445(6) 0.6958(8) 0.120(3) Uani 1 1 d . . . F5' F 0.23052(17) 0.4013(6) 0.6159(8) 0.117(3) Uani 1 1 d . . . F6' F 0.22442(19) 0.2055(9) 0.5545(5) 0.113(3) Uani 1 1 d . . . F7' F 0.2646(2) 0.3162(9) 0.8359(6) 0.120(3) Uani 1 1 d . . . F8' F 0.25012(16) 0.1143(6) 0.7832(6) 0.095(2) Uani 1 1 d . . . F9' F 0.2998(2) 0.1348(11) 0.6158(7) 0.151(4) Uani 1 1 d . . . F10' F 0.30952(19) 0.3425(8) 0.6622(8) 0.144(4) Uani 1 1 d . . . F11' F 0.33101(19) 0.0700(8) 0.8412(8) 0.128(3) Uani 1 1 d . . . F12' F 0.3699(2) 0.1674(9) 0.7532(7) 0.134(3) Uani 1 1 d . . . F13' F 0.3457(3) 0.2706(11) 0.8763(10) 0.192(6) Uani 1 1 d . . . O1' O 0.07069(17) 0.3902(5) 0.5347(5) 0.0554(16) Uani 1 1 d . . . O2' O 0.09437(18) 0.3428(6) 0.7492(5) 0.0554(16) Uani 1 1 d . . . O3' O 0.01855(15) -0.4309(5) 0.3996(4) 0.0400(13) Uani 1 1 d . . . H3' H 0.0303 -0.4874 0.4591 0.048 Uiso 1 1 calc R . . C1' C 0.1466(2) 0.3350(7) 0.5965(7) 0.0371(18) Uani 1 1 d . . . C2' C 0.1815(2) 0.2683(7) 0.6820(7) 0.0392(19) Uani 1 1 d . . . C3' C 0.2242(2) 0.2828(8) 0.6515(7) 0.0412(19) Uani 1 1 d . . . C4' C 0.2598(3) 0.2302(8) 0.7426(7) 0.044(2) Uani 1 1 d . . . C5' C 0.3021(3) 0.2226(10) 0.7051(10) 0.065(3) Uani 1 1 d . . . C6' C 0.3367(3) 0.1822(10) 0.7951(10) 0.065(3) Uani 1 1 d . . . C7' C 0.0807(2) 0.1419(8) 0.6001(6) 0.0369(18) Uani 1 1 d . . . C8' C 0.06142(19) 0.1022(7) 0.4899(6) 0.0290(16) Uani 1 1 d . . . H8' H 0.0558 0.1665 0.4279 0.035 Uiso 1 1 calc R . . C9' C 0.0501(2) -0.0305(7) 0.4685(6) 0.0289(16) Uani 1 1 d . . . C10' C 0.0292(2) -0.0741(8) 0.3572(6) 0.0338(17) Uani 1 1 d . . . H10' H 0.0226 -0.0109 0.2947 0.041 Uiso 1 1 calc R . . C11' C 0.0185(2) -0.2038(7) 0.3386(6) 0.0319(16) Uani 1 1 d . . . H11' H 0.0039 -0.2304 0.2639 0.038 Uiso 1 1 calc R . . C12' C 0.0288(2) -0.3019(8) 0.4293(6) 0.0362(18) Uani 1 1 d . . . C13' C 0.0483(2) -0.2623(8) 0.5380(6) 0.0332(17) Uani 1 1 d . . . H13' H 0.0548 -0.3274 0.5990 0.040 Uiso 1 1 calc R . . C14' C 0.0590(2) -0.1269(7) 0.5621(6) 0.0307(17) Uani 1 1 d . . . C15' C 0.0784(2) -0.0835(8) 0.6743(6) 0.0365(18) Uani 1 1 d . . . H15' H 0.0840 -0.1470 0.7368 0.044 Uiso 1 1 calc R . . C16' C 0.0892(2) 0.0468(8) 0.6953(6) 0.0369(18) Uani 1 1 d . . . H16' H 0.1022 0.0745 0.7716 0.044 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 0.0374(11) 0.0272(11) 0.0650(14) 0.0083(10) 0.0000(10) 0.0050(8) F1 0.056(3) 0.031(3) 0.157(6) -0.032(3) 0.008(3) -0.005(2) F2 0.039(3) 0.106(4) 0.048(3) -0.009(3) 0.006(2) -0.004(3) F3 0.050(3) 0.088(4) 0.069(3) 0.044(3) 0.002(3) -0.003(3) F4 0.042(3) 0.049(3) 0.086(4) -0.027(3) 0.008(3) -0.005(2) F5 0.047(3) 0.088(4) 0.098(4) -0.054(3) 0.002(3) -0.007(3) F6 0.051(3) 0.084(4) 0.071(3) 0.041(3) 0.007(3) -0.003(3) F7 0.048(3) 0.066(4) 0.122(5) 0.053(3) 0.005(3) -0.004(2) F8 0.050(3) 0.101(5) 0.070(3) -0.031(3) 0.011(3) -0.009(3) F9 0.059(4) 0.090(5) 0.136(6) 0.064(4) 0.018(4) 0.026(3) F10 0.043(3) 0.183(7) 0.049(3) -0.008(4) 0.002(2) -0.014(4) F11 0.057(4) 0.129(6) 0.065(4) -0.007(4) 0.022(3) -0.008(3) F12 0.029(3) 0.230(9) 0.103(5) 0.078(5) 0.001(3) 0.006(4) F13 0.067(4) 0.082(5) 0.140(6) 0.001(4) 0.024(4) -0.024(3) O1 0.053(4) 0.055(4) 0.063(4) 0.029(3) -0.002(3) -0.001(3) O2 0.045(4) 0.027(3) 0.110(5) -0.006(3) 0.014(3) 0.012(2) O3 0.047(3) 0.029(3) 0.044(3) 0.000(2) 0.014(2) -0.002(2) C1 0.041(5) 0.034(5) 0.055(5) -0.006(4) -0.008(4) 0.001(3) C2 0.044(5) 0.026(4) 0.053(5) 0.001(4) 0.005(4) -0.004(3) C3 0.040(5) 0.033(5) 0.055(5) -0.006(4) 0.006(4) -0.007(3) C4 0.043(5) 0.034(5) 0.039(4) -0.001(4) -0.003(4) -0.008(3) C5 0.044(5) 0.060(6) 0.052(5) 0.020(5) 0.004(4) -0.001(4) C6 0.043(6) 0.086(8) 0.055(6) 0.027(6) -0.002(4) 0.009(5) C7 0.026(4) 0.037(5) 0.047(5) 0.002(4) -0.005(3) 0.007(3) C8 0.027(4) 0.035(4) 0.031(4) -0.006(3) -0.002(3) 0.014(3) C9 0.030(4) 0.021(4) 0.025(3) -0.003(3) 0.000(3) 0.001(3) C10 0.030(4) 0.040(5) 0.029(4) -0.009(3) 0.006(3) 0.010(3) C11 0.035(4) 0.036(5) 0.029(4) 0.000(3) 0.006(3) -0.001(3) C12 0.031(4) 0.021(4) 0.030(4) -0.003(3) -0.001(3) 0.000(3) C13 0.034(4) 0.034(4) 0.025(3) -0.010(3) 0.005(3) 0.004(3) C14 0.025(4) 0.031(4) 0.026(4) -0.007(3) -0.004(3) 0.005(3) C15 0.030(4) 0.037(5) 0.031(4) -0.009(3) 0.004(3) -0.003(3) C16 0.038(4) 0.027(4) 0.035(4) -0.001(3) 0.004(3) -0.002(3) S1' 0.0411(12) 0.0303(11) 0.0560(13) -0.0043(10) 0.0150(9) 0.0077(8) F1' 0.054(3) 0.028(3) 0.141(5) 0.021(3) 0.012(3) 0.003(2) F2' 0.039(3) 0.139(5) 0.039(3) -0.002(3) 0.010(2) 0.009(3) F3' 0.070(4) 0.218(9) 0.051(3) -0.022(4) 0.014(3) 0.030(5) F4' 0.040(3) 0.062(4) 0.244(9) 0.074(5) -0.016(4) -0.012(3) F5' 0.046(4) 0.076(4) 0.232(8) 0.102(5) 0.028(4) 0.013(3) F6' 0.057(4) 0.217(9) 0.061(4) -0.040(4) 0.000(3) 0.040(4) F7' 0.102(6) 0.177(8) 0.077(4) -0.060(5) 0.003(4) 0.016(5) F8' 0.050(4) 0.088(5) 0.140(5) 0.083(4) -0.004(3) -0.006(3) F9' 0.077(5) 0.247(11) 0.122(6) -0.076(7) -0.001(4) 0.048(6) F10' 0.048(4) 0.153(7) 0.231(9) 0.141(7) 0.020(5) 0.001(4) F11' 0.051(4) 0.125(6) 0.201(8) 0.098(6) 0.002(4) 0.005(4) F12' 0.045(4) 0.190(9) 0.167(7) 0.094(6) 0.016(4) 0.014(4) F13' 0.121(8) 0.179(9) 0.233(11) -0.125(8) -0.106(7) 0.056(6) O1' 0.048(4) 0.035(3) 0.082(4) 0.006(3) 0.007(3) 0.014(3) O2' 0.057(4) 0.054(4) 0.061(4) -0.021(3) 0.027(3) -0.002(3) O3' 0.041(3) 0.036(3) 0.042(3) 0.002(2) 0.005(2) -0.001(2) C1' 0.039(5) 0.027(5) 0.044(5) 0.003(3) 0.001(3) 0.004(3) C2' 0.047(5) 0.028(4) 0.043(5) -0.002(4) 0.007(4) -0.002(3) C3' 0.045(5) 0.039(5) 0.039(4) 0.003(4) 0.004(4) 0.009(4) C4' 0.056(6) 0.032(5) 0.047(5) 0.005(4) 0.015(4) 0.000(4) C5' 0.050(6) 0.053(6) 0.088(7) 0.014(6) 0.002(5) -0.001(4) C6' 0.045(6) 0.042(6) 0.105(8) 0.017(6) 0.007(6) -0.006(4) C7' 0.029(4) 0.044(5) 0.042(4) 0.006(4) 0.017(3) 0.009(3) C8' 0.023(4) 0.033(4) 0.032(4) 0.010(3) 0.008(3) 0.013(3) C9' 0.024(4) 0.032(4) 0.031(4) 0.009(3) 0.005(3) 0.009(3) C10' 0.031(4) 0.041(5) 0.029(4) 0.013(3) 0.004(3) 0.010(3) C11' 0.029(4) 0.040(5) 0.028(4) 0.006(3) 0.008(3) 0.005(3) C12' 0.028(4) 0.044(5) 0.039(4) -0.002(4) 0.015(3) 0.000(3) C13' 0.023(4) 0.044(5) 0.032(4) 0.010(3) 0.002(3) 0.000(3) C14' 0.021(4) 0.042(5) 0.031(4) 0.002(3) 0.010(3) 0.005(3) C15' 0.038(4) 0.041(5) 0.030(4) 0.009(4) 0.003(3) 0.005(3) C16' 0.030(4) 0.053(5) 0.029(4) -0.001(4) 0.005(3) 0.003(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 O1 1.432(6) . ? S1 O2 1.429(6) . ? S1 C7 1.738(8) . ? S1 C1 1.875(8) . ? F1 C1 1.334(9) . ? F2 C1 1.352(9) . ? F3 C2 1.333(9) . ? F4 C2 1.330(8) . ? F5 C3 1.323(9) . ? F6 C3 1.333(9) . ? F7 C4 1.331(8) . ? F8 C4 1.339(9) . ? F9 C5 1.345(10) . ? F10 C5 1.342(10) . ? F11 C6 1.318(10) . ? F12 C6 1.293(10) . ? F13 C6 1.319(11) . ? O3 C12 1.350(8) . ? C1 C2 1.530(11) . ? C2 C3 1.551(11) . ? C3 C4 1.536(11) . ? C4 C5 1.532(11) . ? C5 C6 1.522(12) . ? C7 C8 1.372(10) . ? C7 C16 1.417(10) . ? C8 C9 1.391(10) . ? C9 C10 1.432(9) . ? C9 C14 1.435(9) . ? C10 C11 1.368(10) . ? C11 C12 1.418(10) . ? C12 C13 1.371(9) . ? C13 C14 1.405(10) . ? C14 C15 1.420(10) . ? C15 C16 1.345(10) . ? S1' O2' 1.424(6) . ? S1' O1' 1.444(6) . ? S1' C7' 1.739(8) . ? S1' C1' 1.873(8) . ? F1' C1' 1.326(8) . ? F2' C1' 1.315(8) . ? F3' C2' 1.348(9) . ? F4' C2' 1.282(9) . ? F5' C3' 1.275(9) . ? F6' C3' 1.348(9) . ? F7' C4' 1.356(10) . ? F8' C4' 1.302(9) . ? F9' C5' 1.336(12) . ? F10' C5' 1.327(11) . ? F11' C6' 1.261(10) . ? F12' C6' 1.279(11) . ? F13' C6' 1.278(12) . ? O3' C12' 1.356(9) . ? C1' C2' 1.543(10) . ? C2' C3' 1.525(11) . ? C3' C4' 1.536(11) . ? C4' C5' 1.539(13) . ? C5' C6' 1.472(13) . ? C7' C8' 1.377(10) . ? C7' C16' 1.434(10) . ? C8' C9' 1.384(10) . ? C9' C10' 1.416(10) . ? C9' C14' 1.431(9) . ? C10' C11' 1.346(10) . ? C11' C12' 1.424(10) . ? C12' C13' 1.364(10) . ? C13' C14' 1.409(10) . ? C14' C15' 1.406(10) . ? C15' C16' 1.356(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 O1 S1 O2 120.9(4) . . ? O1 S1 C7 110.7(4) . . ? O2 S1 C7 108.9(4) . . ? O1 S1 C1 105.7(4) . . ? O2 S1 C1 102.0(4) . . ? C7 S1 C1 107.5(3) . . ? F1 C1 F2 109.9(7) . . ? F1 C1 C2 109.2(7) . . ? F2 C1 C2 108.9(6) . . ? F1 C1 S1 104.2(5) . . ? F2 C1 S1 106.8(5) . . ? C2 C1 S1 117.7(6) . . ? F4 C2 F3 107.6(7) . . ? F4 C2 C1 108.3(6) . . ? F3 C2 C1 107.8(6) . . ? F4 C2 C3 109.1(6) . . ? F3 C2 C3 109.8(6) . . ? C1 C2 C3 114.0(7) . . ? F5 C3 F6 109.7(7) . . ? F5 C3 C4 107.4(6) . . ? F6 C3 C4 107.8(6) . . ? F5 C3 C2 108.8(6) . . ? F6 C3 C2 108.8(6) . . ? C4 C3 C2 114.2(7) . . ? F7 C4 F8 106.3(6) . . ? F7 C4 C3 109.2(7) . . ? F8 C4 C3 109.1(6) . . ? F7 C4 C5 106.9(6) . . ? F8 C4 C5 108.4(7) . . ? C3 C4 C5 116.4(7) . . ? F10 C5 F9 107.0(7) . . ? F10 C5 C6 107.2(8) . . ? F9 C5 C6 108.0(8) . . ? F10 C5 C4 109.1(7) . . ? F9 C5 C4 107.8(7) . . ? C6 C5 C4 117.3(7) . . ? F12 C6 F13 108.7(9) . . ? F12 C6 F11 108.4(9) . . ? F13 C6 F11 107.9(8) . . ? F12 C6 C5 110.8(7) . . ? F13 C6 C5 111.1(8) . . ? F11 C6 C5 110.0(8) . . ? C8 C7 C16 121.1(7) . . ? C8 C7 S1 118.9(6) . . ? C16 C7 S1 119.8(6) . . ? C7 C8 C9 120.7(6) . . ? C8 C9 C10 122.0(6) . . ? C8 C9 C14 119.2(6) . . ? C10 C9 C14 118.8(6) . . ? C11 C10 C9 120.1(6) . . ? C10 C11 C12 120.5(7) . . ? O3 C12 C13 123.6(6) . . ? O3 C12 C11 115.8(6) . . ? C13 C12 C11 120.6(6) . . ? C12 C13 C14 120.7(6) . . ? C13 C14 C15 123.1(6) . . ? C13 C14 C9 119.3(6) . . ? C15 C14 C9 117.6(6) . . ? C16 C15 C14 122.7(7) . . ? C15 C16 C7 118.6(7) . . ? O2' S1' O1' 120.9(3) . . ? O2' S1' C7' 111.3(4) . . ? O1' S1' C7' 108.3(4) . . ? O2' S1' C1' 106.3(3) . . ? O1' S1' C1' 100.9(3) . . ? C7' S1' C1' 107.9(3) . . ? F2' C1' F1' 110.0(7) . . ? F2' C1' C2' 108.9(6) . . ? F1' C1' C2' 108.2(6) . . ? F2' C1' S1' 107.8(5) . . ? F1' C1' S1' 104.3(5) . . ? C2' C1' S1' 117.4(5) . . ? F4' C2' F3' 105.6(8) . . ? F4' C2' C3' 111.1(7) . . ? F3' C2' C3' 106.5(6) . . ? F4' C2' C1' 109.1(6) . . ? F3' C2' C1' 107.1(6) . . ? C3' C2' C1' 116.8(6) . . ? F5' C3' F6' 104.1(8) . . ? F5' C3' C2' 111.5(6) . . ? F6' C3' C2' 105.1(7) . . ? F5' C3' C4' 112.5(7) . . ? F6' C3' C4' 105.0(6) . . ? C2' C3' C4' 117.3(6) . . ? F8' C4' F7' 106.5(7) . . ? F8' C4' C3' 109.6(7) . . ? F7' C4' C3' 107.5(7) . . ? F8' C4' C5' 110.1(7) . . ? F7' C4' C5' 104.5(8) . . ? C3' C4' C5' 117.9(7) . . ? F10' C5' F9' 107.3(10) . . ? F10' C5' C6' 109.4(8) . . ? F9' C5' C6' 107.2(9) . . ? F10' C5' C4' 106.9(8) . . ? F9' C5' C4' 107.6(8) . . ? C6' C5' C4' 118.0(9) . . ? F11' C6' F13' 109.9(11) . . ? F11' C6' F12' 104.5(9) . . ? F13' C6' F12' 103.6(9) . . ? F11' C6' C5' 112.3(8) . . ? F13' C6' C5' 112.6(9) . . ? F12' C6' C5' 113.3(10) . . ? C8' C7' C16' 120.7(7) . . ? C8' C7' S1' 120.4(6) . . ? C16' C7' S1' 118.9(6) . . ? C7' C8' C9' 120.7(6) . . ? C8' C9' C10' 122.2(6) . . ? C8' C9' C14' 119.2(6) . . ? C10' C9' C14' 118.6(6) . . ? C11' C10' C9' 121.0(6) . . ? C10' C11' C12' 121.0(7) . . ? O3' C12' C13' 124.4(7) . . ? O3' C12' C11' 116.4(7) . . ? C13' C12' C11' 119.2(7) . . ? C12' C13' C14' 121.5(7) . . ? C13' C14' C15' 122.4(6) . . ? C13' C14' C9' 118.6(6) . . ? C15' C14' C9' 119.0(7) . . ? C16' C15' C14' 121.7(7) . . ? C15' C16' C7' 118.8(7) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.903 _refine_diff_density_min -0.600 _refine_diff_density_rms 0.097