# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2008 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr John Holbrey' _publ_contact_author_email J.HOLBREY@QUB.AC.UK _publ_section_title ; Influence of electron-withdrawing groups on the ionic liquid characteristics of 1-alkyl-n-cyanopyridinium and 1-alkyl-n-(trifluoromethyl)pyridinium salts ; loop_ _publ_author_name 'John Holbrey' 'Chris Hardacre' 'Claire L. Mullan' 'Mark Nieuwenhuyzen' 'W. Matthew Reichert' ; K.Seddon ; 'Simon J. Teat' # Attachment 'B805063E_renumbered_structures.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 646907' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-Methyl-4-cyanopyridinium methylsulfate ; _chemical_name_common '1-Methyl-4-cyanopyridinium methylsulfate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H10 N2 O4 S' _chemical_formula_weight 230.24 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' 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 Orthorhombic _symmetry_space_group_name_H-M Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 19.4965(15) _cell_length_b 8.5428(7) _cell_length_c 6.2274(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1037.20(14) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.474 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.308 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9409 _exptl_absorpt_correction_T_max 0.9908 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.77490 _diffrn_radiation_type 'synchrotron radiation' _diffrn_radiation_source 'advanced light source station 11.3.1' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker Platinum 200 CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24308 _diffrn_reflns_av_R_equivalents 0.0653 _diffrn_reflns_av_sigmaI/netI 0.0374 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 33.64 _reflns_number_total 3147 _reflns_number_gt 3079 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT v7.34a' _computing_data_reduction 'Bruker SAINT v7.34a' _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 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^)+(0.0827P)^2^+0.0583P] 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 geom _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.05(7) _refine_ls_number_reflns 3147 _refine_ls_number_parameters 137 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0422 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_ref 0.1177 _refine_ls_wR_factor_gt 0.1016 _refine_ls_goodness_of_fit_ref 1.150 _refine_ls_restrained_S_all 1.150 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 33.64 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.844 _refine_diff_density_min -0.999 _refine_diff_density_rms 0.289 loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags N1 N Uani 0.45673 0.42500 -0.01180 1.000 0.0521 . . N2 N Uani 0.31525 0.43311 0.71578 1.000 0.0249 . . C2 C Uani 0.42776 0.42730 0.14760 1.000 0.0390 . . C3 C Uani 0.38968 0.42994 0.34590 1.000 0.0301 . . C4 C Uani 0.36421 0.29061 0.42920 1.000 0.0312 . . C5 C Uani 0.32682 0.29589 0.61700 1.000 0.0286 . . C6 C Uani 0.33920 0.56829 0.63580 1.000 0.0309 . . C7 C Uani 0.37688 0.57100 0.44930 1.000 0.0335 . . C8 C Uani 0.27313 0.43518 0.91260 1.000 0.0318 . . S1 S Uani 0.14568 0.44291 0.45484 1.000 0.0256 . . O1 O Uani 0.07354 0.49207 0.55480 1.000 0.0462 . . O2 O Uani 0.16422 0.29509 0.55290 1.000 0.0369 . . O3 O Uani 0.18761 0.57264 0.52270 1.000 0.0395 . . O4 O Uani 0.13626 0.43232 0.22520 1.000 0.0392 . . C1 C Uani 0.01801 0.38330 0.52270 1.000 0.0550 . . H4 H Uiso 0.39370 0.66680 0.39270 1.000 0.0402 . . H5 H Uiso 0.33000 0.66350 0.70910 1.000 0.0370 . . H6 H Uiso 0.26890 0.54300 0.96470 1.000 0.0477 . . H7 H Uiso 0.22750 0.39330 0.88070 1.000 0.0477 . . H8 H Uiso 0.29510 0.37060 1.02300 1.000 0.0477 . . H9 H Uiso 0.30910 0.20190 0.67680 1.000 0.0344 . . H10 H Uiso 0.37240 0.19390 0.35830 1.000 0.0374 . . H1 H Uiso -0.02550 0.43410 0.55920 1.000 0.0825 . . H2 H Uiso 0.02470 0.29170 0.61490 1.000 0.0825 . . H3 H Uiso 0.01710 0.35030 0.37200 1.000 0.0825 . . 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 N1 0.0378 0.0785 0.0401 0.0010 0.0080 -0.0040 N2 0.0264 0.0240 0.0242 0.0003 -0.0036 0.0009 C2 0.0284 0.0550 0.0336 0.0023 -0.0003 -0.0023 C3 0.0238 0.0387 0.0278 0.0023 -0.0033 -0.0005 C4 0.0338 0.0289 0.0309 -0.0055 -0.0011 0.0002 C5 0.0329 0.0232 0.0298 -0.0002 -0.0020 -0.0010 C6 0.0351 0.0228 0.0347 0.0002 -0.0008 -0.0008 C7 0.0339 0.0301 0.0365 0.0055 -0.0003 -0.0042 C8 0.0343 0.0368 0.0243 -0.0002 0.0010 0.0033 S1 0.0272 0.0234 0.0262 -0.0001 -0.0021 0.0002 O1 0.0355 0.0470 0.0560 -0.0137 0.0083 0.0028 O2 0.0456 0.0258 0.0392 0.0038 -0.0089 0.0023 O3 0.0445 0.0297 0.0443 0.0024 -0.0128 -0.0086 O4 0.0535 0.0380 0.0262 0.0002 -0.0032 0.0007 C1 0.0314 0.0627 0.0709 0.0000 0.0039 -0.0050 _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O3 1.4405 . . yes S1 O1 1.5944 . . yes S1 O2 1.4485 . . yes S1 O4 1.4446 . . yes O1 C1 1.4407 . . yes N1 C2 1.1423 . . yes N2 C5 1.3429 . . yes N2 C6 1.3415 . . yes N2 C8 1.4755 . . yes C2 C3 1.4411 . . no C3 C4 1.3901 . . no C3 C7 1.3889 . . no C4 C5 1.3788 . . no C6 C7 1.3744 . . no C4 H10 0.9500 . . no C5 H9 0.9500 . . no C6 H5 0.9500 . . no C7 H4 0.9500 . . no C8 H7 0.9800 . . no C8 H8 0.9800 . . no C8 H6 0.9800 . . no C1 H1 0.9800 . . no C1 H2 0.9800 . . no C1 H3 0.9800 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 S1 O4 114.25 . . . yes O1 S1 O3 100.57 . . . yes O1 S1 O4 106.91 . . . yes O1 S1 O2 106.57 . . . yes O2 S1 O4 113.23 . . . yes O2 S1 O3 113.92 . . . yes S1 O1 C1 116.03 . . . yes C6 N2 C8 119.46 . . . yes C5 N2 C8 118.98 . . . yes C5 N2 C6 121.53 . . . yes N1 C2 C3 178.62 . . . yes C2 C3 C4 119.37 . . . no C2 C3 C7 120.23 . . . no C4 C3 C7 120.38 . . . no C3 C4 C5 118.51 . . . no N2 C5 C4 120.39 . . . yes N2 C6 C7 120.95 . . . yes C3 C7 C6 118.24 . . . no C5 C4 H10 121.00 . . . no C3 C4 H10 121.00 . . . no N2 C5 H9 120.00 . . . no C4 C5 H9 120.00 . . . no C7 C6 H5 120.00 . . . no N2 C6 H5 120.00 . . . no C3 C7 H4 121.00 . . . no C6 C7 H4 121.00 . . . no N2 C8 H6 109.00 . . . no N2 C8 H7 109.00 . . . no N2 C8 H8 109.00 . . . no H6 C8 H7 110.00 . . . no H6 C8 H8 109.00 . . . no H7 C8 H8 109.00 . . . no O1 C1 H1 109.00 . . . no O1 C1 H2 110.00 . . . no O1 C1 H3 109.00 . . . no H1 C1 H2 109.00 . . . no H1 C1 H3 110.00 . . . no H2 C1 H3 110.00 . . . no 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 O2 S1 O1 C1 -59.17 . . . . no O3 S1 O1 C1 -178.23 . . . . no O4 S1 O1 C1 62.20 . . . . no C5 N2 C6 C7 -0.27 . . . . no C8 N2 C6 C7 -178.07 . . . . no C8 N2 C5 C4 178.02 . . . . no C6 N2 C5 C4 0.21 . . . . no C2 C3 C7 C6 178.74 . . . . no C2 C3 C4 C5 -178.82 . . . . no C7 C3 C4 C5 -0.69 . . . . no C4 C3 C7 C6 0.63 . . . . no C3 C4 C5 N2 0.27 . . . . no N2 C6 C7 C3 -0.15 . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag S1 H9 2.9400 . 3_554 no S1 H5 2.8700 . 3_544 no S1 H7 3.1200 . . no O2 C7 3.2250 . 3_545 no O2 C8 3.3104 . . no O2 C5 3.1952 . . no O2 C6 3.2412 . 3_544 no O3 C6 3.0385 . . no O3 N2 3.0099 . . no O3 C8 3.2631 . 3_554 no O3 C8 3.1709 . . no O3 C5 3.1780 . 3_554 no O3 C4 3.3009 . 3_555 no O4 C6 3.1953 . 3_544 no O4 C5 3.2586 . 3_554 no O4 C8 3.3032 . 1_554 no O1 H10 2.7700 . 3_555 no O2 H7 2.5300 . . no O2 H5 2.4200 . 3_544 no O2 H4 2.6400 . 3_545 no O2 H2 2.7500 . . no O2 H6 2.5800 . 3_544 no O3 H7 2.8100 . . no O3 H10 2.6100 . 3_555 no O3 H8 2.5700 . 3_554 no O3 H9 2.4200 . 3_554 no O4 H3 2.5900 . . no O4 H9 2.5600 . 3_554 no O4 H5 2.3900 . 3_544 no O4 H1 2.6500 . 2_564 no O4 H7 2.8100 . 1_554 no N1 C2 3.3411 . 2_664 no N1 N2 3.2390 . 1_554 no N1 C6 3.4007 . 1_554 no N1 C3 3.3597 . 2_664 no N1 C7 3.2532 . 2_664 no N2 O3 3.0099 . . no N2 N1 3.2390 . 1_556 no C1 C4 3.3967 . 4_455 no C2 C8 3.3518 . 1_554 no C2 N1 3.3411 . 2_665 no C3 C8 3.5279 . 1_554 no C3 N1 3.3597 . 2_665 no C4 C1 3.3967 . 4_555 no C4 O3 3.3009 . 3_544 no C5 O4 3.2586 . 3_545 no C5 O3 3.1780 . 3_545 no C5 O2 3.1952 . . no C6 O2 3.2412 . 3_555 no C6 N1 3.4007 . 1_556 no C6 O3 3.0385 . . no C6 O4 3.1953 . 3_555 no C7 N1 3.2532 . 2_665 no C7 O2 3.2250 . 3_554 no C8 O3 3.1709 . . no C8 O4 3.3032 . 1_556 no C8 C3 3.5279 . 1_556 no C8 O3 3.2631 . 3_545 no C8 C2 3.3518 . 1_556 no C8 O2 3.3104 . . no C1 H10 3.0900 . 4_455 no C2 H8 2.7400 . 1_554 no C3 H8 2.7800 . 1_554 no C4 H8 2.9500 . 1_554 no C4 H1 2.9900 . 4_555 no C5 H6 3.0100 . 3_544 no H1 H10 2.5900 . 4_455 no H1 O4 2.6500 . 2_565 no H1 C4 2.9900 . 4_455 no H2 H4 2.5800 . 3_545 no H2 O2 2.7500 . . no H3 O4 2.5900 . . no H4 O2 2.6400 . 3_554 no H4 H2 2.5800 . 3_554 no H5 S1 2.8700 . 3_555 no H5 O2 2.4200 . 3_555 no H5 O4 2.3900 . 3_555 no H5 H6 2.2400 . . no H6 H5 2.2400 . . no H6 O2 2.5800 . 3_555 no H6 H9 2.4300 . 3_555 no H6 C5 3.0100 . 3_555 no H7 S1 3.1200 . . no H7 O2 2.5300 . . no H7 O3 2.8100 . . no H7 O4 2.8100 . 1_556 no H8 C2 2.7400 . 1_556 no H8 C3 2.7800 . 1_556 no H8 C4 2.9500 . 1_556 no H8 O3 2.5700 . 3_545 no H9 O3 2.4200 . 3_545 no H9 O4 2.5600 . 3_545 no H9 H6 2.4300 . 3_544 no H9 S1 2.9400 . 3_545 no H10 O1 2.7700 . 3_544 no H10 C1 3.0900 . 4_555 no H10 H1 2.5900 . 4_555 no H10 O3 2.6100 . 3_544 no #===END data_37 _database_code_depnum_ccdc_archive 'CCDC 646908' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-Ethyl-3-(trifluoromethyl)pyridinium bis{(trifluoromethyl)sulfonyl}amide ; _chemical_name_common ;1-Ethyl-3-(trifluoromethyl)pyridinium bis((trifluoromethyl)sulfonyl)amide ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H9 F9 N2 O4 S2' _chemical_formula_weight 456.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C -0.0020 0.0020 '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 -0.0031 0.0040 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O -0.0042 0.0074 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F -0.0053 0.0125 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1206 0.1480 '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 10.8446(15) _cell_length_b 12.866(2) _cell_length_c 13.2369(19) _cell_angle_alpha 90.366(5) _cell_angle_beta 90.689(4) _cell_angle_gamma 114.836(3) _cell_volume 1675.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.809 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.544 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9476 _exptl_absorpt_correction_T_max 0.9786 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.77490 _diffrn_radiation_type 'synchrotron radiation' _diffrn_radiation_source 'advanced light source station 11.3.1' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker Platinum 200 CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19285 _diffrn_reflns_av_R_equivalents 0.0656 _diffrn_reflns_av_sigmaI/netI 0.0780 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 31.18 _reflns_number_total 8319 _reflns_number_gt 6004 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT v7.34a' _computing_data_reduction 'Bruker SAINT v7.34a' _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 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^)+(0.1286P)^2^+2.5580P] 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 geom _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8319 _refine_ls_number_parameters 487 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1033 _refine_ls_R_factor_gt 0.0792 _refine_ls_wR_factor_ref 0.2397 _refine_ls_wR_factor_gt 0.2184 _refine_ls_goodness_of_fit_ref 0.992 _refine_ls_restrained_S_all 0.993 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 31.18 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.272 _refine_diff_density_min -0.719 _refine_diff_density_rms 0.109 loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags F13 F Uiso 0.67650 -0.19430 0.80180 0.504 0.0660 . . F14 F Uiso 0.88470 -0.10570 0.76660 0.504 0.0740 . . F15 F Uiso 0.80420 -0.03900 0.88300 0.504 0.0880 . . N3 N Uani 0.79560 0.09680 0.57750 1.000 0.0334 . . C5 C Uani 0.77870 -0.08970 0.79310 0.504 0.0562 . . C6 C Uani 0.73860 -0.02170 0.71870 1.000 0.0410 . . C7 C Uani 0.83010 0.03720 0.64600 1.000 0.0380 . . C8 C Uani 0.67440 0.10150 0.57900 1.000 0.0375 . . C9 C Uani 0.58120 0.04440 0.65080 1.000 0.0432 . . C10 C Uani 0.61340 -0.01890 0.72200 1.000 0.0444 . . C11 C Uani 0.89400 0.15960 0.49820 1.000 0.0420 . . C12 C Uani 0.96700 0.28410 0.52560 1.000 0.0590 . . F16 F Uani 0.10450 0.59820 0.24850 1.000 0.0827 . . F17 F Uani 0.30030 0.67200 0.31570 1.000 0.0772 . . F18 F Uani 0.15400 0.51290 0.36550 1.000 0.0916 . . N4 N Uani 0.20760 0.39750 0.06500 1.000 0.0451 . . C13 C Uani 0.20260 0.57430 0.28500 1.000 0.0505 . . C14 C Uani 0.25150 0.51430 0.20890 1.000 0.0393 . . C15 C Uani 0.16480 0.45190 0.13330 1.000 0.0426 . . C16 C Uani 0.33230 0.39970 0.07130 1.000 0.0425 . . C17 C Uani 0.42090 0.46130 0.14560 1.000 0.0474 . . C18 C Uani 0.38100 0.52030 0.21530 1.000 0.0479 . . C19 C Uani 0.11430 0.33860 -0.02370 1.000 0.0589 . . C20 C Uani 0.03750 0.21710 0.00270 1.000 0.0779 . . S1 S Uani 0.69843 0.31759 0.06226 1.000 0.0349 . . S2 S Uani 0.75298 0.28533 0.26344 1.000 0.0389 . . F1 F Uani 0.61850 0.39610 0.33280 1.000 0.0864 . . F2 F Uani 0.81450 0.44300 0.40320 1.000 0.0888 . . F3 F Uani 0.79880 0.50060 0.25470 1.000 0.0742 . . F4 F Uani 0.70850 0.12850 0.00280 1.000 0.0992 . . F5 F Uani 0.65270 0.21730 -0.11140 1.000 0.1009 . . F6 F Uani 0.50960 0.12370 0.00040 1.000 0.0882 . . O1 O Uani 0.61400 0.37180 0.03300 1.000 0.0558 . . O2 O Uani 0.84070 0.37740 0.04280 1.000 0.0492 . . O3 O Uani 0.68610 0.19870 0.33560 1.000 0.0558 . . O4 O Uani 0.89230 0.31640 0.24560 1.000 0.0525 . . N1 N Uani 0.65840 0.26150 0.16840 1.000 0.0454 . . C1 C Uani 0.74650 0.41380 0.31720 1.000 0.0547 . . C2 C Uani 0.63840 0.18860 -0.01600 1.000 0.0586 . . S3 S Uani 0.25800 0.19152 0.76552 1.000 0.0400 . . S4 S Uani 0.31499 0.18072 0.56155 1.000 0.0358 . . F7 F Uani 0.49540 0.38760 0.52750 1.000 0.0690 . . F8 F Uani 0.29640 0.37490 0.55940 1.000 0.0871 . . F9 F Uani 0.33760 0.31990 0.41580 1.000 0.0897 . . F10 F Uani 0.16040 -0.02970 0.74130 1.000 0.0703 . . F11 F Uani 0.34620 0.04040 0.82500 1.000 0.0734 . . F12 F Uani 0.16270 0.02710 0.89470 1.000 0.0752 . . O5 O Uani 0.33230 0.26710 0.84610 1.000 0.0591 . . O6 O Uani 0.12540 0.18180 0.74040 1.000 0.0509 . . O7 O Uani 0.17320 0.12090 0.53830 1.000 0.0476 . . O8 O Uani 0.40560 0.14210 0.51470 1.000 0.0514 . . N2 N Uani 0.35680 0.20750 0.67540 1.000 0.0446 . . C3 C Uani 0.36420 0.32390 0.51310 1.000 0.0521 . . C4 C Uani 0.23130 0.04970 0.80940 1.000 0.0503 . . H1 H Uiso 0.55020 -0.05970 0.77230 1.000 0.0532 . . H2 H Uiso 0.49560 0.04810 0.65180 1.000 0.0518 . . H3 H Uiso 0.65290 0.14500 0.52970 1.000 0.0450 . . H4 H Uiso 1.02970 0.32440 0.47170 1.000 0.0886 . . H5 H Uiso 0.90080 0.31690 0.53410 1.000 0.0886 . . H6 H Uiso 1.01830 0.29260 0.58900 1.000 0.0886 . . H7 H Uiso 0.96070 0.12630 0.49030 1.000 0.0504 . . H8 H Uiso 0.84510 0.15120 0.43290 1.000 0.0504 . . H9 H Uiso 0.91700 0.03580 0.64440 1.000 0.0457 . . H10 H Uiso 0.44210 0.56460 0.26720 1.000 0.0575 . . H11 H Uiso 0.50960 0.46370 0.14930 1.000 0.0568 . . H12 H Uiso 0.35880 0.35780 0.02350 1.000 0.0510 . . H13 H Uiso -0.02600 0.17700 -0.05250 1.000 0.1168 . . H14 H Uiso 0.10090 0.18180 0.01360 1.000 0.1168 . . H15 H Uiso -0.01320 0.21200 0.06470 1.000 0.1168 . . H16 H Uiso 0.16800 0.34490 -0.08510 1.000 0.0707 . . H17 H Uiso 0.05110 0.37460 -0.03700 1.000 0.0707 . . H18 H Uiso 0.07500 0.44710 0.12910 1.000 0.0511 . . 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 N3 0.0311 0.0285 0.0386 -0.0022 -0.0014 0.0105 C5 0.0480 0.0560 0.0590 0.0140 0.0020 0.0160 C6 0.0370 0.0336 0.0450 -0.0013 -0.0056 0.0079 C7 0.0349 0.0345 0.0440 -0.0037 -0.0073 0.0141 C8 0.0356 0.0337 0.0440 -0.0033 -0.0062 0.0157 C9 0.0321 0.0430 0.0550 -0.0010 0.0023 0.0164 C10 0.0380 0.0430 0.0480 0.0007 0.0007 0.0130 C11 0.0400 0.0440 0.0420 0.0045 0.0050 0.0174 C12 0.0610 0.0400 0.0640 0.0080 0.0100 0.0090 F16 0.0760 0.1040 0.0860 -0.0350 -0.0016 0.0560 F17 0.0680 0.0528 0.0920 -0.0342 0.0110 0.0073 F18 0.1320 0.0670 0.0587 -0.0020 0.0480 0.0240 N4 0.0363 0.0470 0.0499 -0.0122 0.0018 0.0157 C13 0.0500 0.0430 0.0480 -0.0093 0.0103 0.0090 C14 0.0400 0.0344 0.0377 0.0023 0.0067 0.0098 C15 0.0336 0.0450 0.0460 -0.0071 0.0054 0.0134 C16 0.0420 0.0380 0.0480 0.0008 0.0074 0.0170 C17 0.0370 0.0500 0.0550 0.0021 0.0013 0.0182 C18 0.0400 0.0510 0.0480 -0.0054 -0.0026 0.0146 C19 0.0530 0.0550 0.0700 -0.0100 0.0060 0.0240 C20 0.0840 0.0560 0.0830 -0.0040 0.0020 0.0190 S1 0.0344 0.0304 0.0376 0.0031 0.0040 0.0111 S2 0.0365 0.0360 0.0395 0.0024 -0.0003 0.0106 F1 0.0810 0.1050 0.0910 -0.0080 0.0215 0.0560 F2 0.1250 0.0860 0.0620 -0.0316 -0.0300 0.0520 F3 0.1010 0.0402 0.0810 0.0014 0.0051 0.0291 F4 0.1390 0.0530 0.1220 -0.0020 0.0220 0.0560 F5 0.1530 0.0710 0.0450 -0.0093 0.0140 0.0140 F6 0.0820 0.0590 0.0780 -0.0092 -0.0105 -0.0147 O1 0.0555 0.0580 0.0650 0.0176 0.0106 0.0343 O2 0.0375 0.0467 0.0561 0.0135 0.0109 0.0102 O3 0.0560 0.0526 0.0461 0.0141 -0.0015 0.0101 O4 0.0394 0.0600 0.0592 0.0014 -0.0022 0.0219 N1 0.0347 0.0480 0.0393 0.0043 0.0012 0.0034 C1 0.0640 0.0600 0.0450 -0.0020 0.0010 0.0310 C2 0.0740 0.0400 0.0500 -0.0001 0.0100 0.0120 S3 0.0353 0.0372 0.0406 -0.0054 0.0035 0.0086 S4 0.0360 0.0321 0.0385 -0.0044 -0.0020 0.0138 F7 0.0585 0.0501 0.0800 0.0119 0.0124 0.0044 F8 0.0880 0.0468 0.1410 0.0084 0.0290 0.0416 F9 0.0990 0.0920 0.0690 0.0323 -0.0111 0.0310 F10 0.0810 0.0398 0.0790 -0.0099 -0.0035 0.0149 F11 0.0700 0.0880 0.0760 0.0138 -0.0010 0.0466 F12 0.0930 0.0660 0.0643 0.0194 0.0328 0.0300 O5 0.0560 0.0536 0.0498 -0.0200 0.0018 0.0058 O6 0.0444 0.0507 0.0598 -0.0014 0.0066 0.0219 O7 0.0405 0.0455 0.0518 -0.0090 -0.0094 0.0137 O8 0.0549 0.0540 0.0534 -0.0140 -0.0040 0.0311 N2 0.0347 0.0530 0.0368 -0.0026 0.0021 0.0094 C3 0.0520 0.0470 0.0600 0.0100 0.0070 0.0230 C4 0.0540 0.0510 0.0460 0.0015 0.0068 0.0220 #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C2 1.8181 . . yes S1 O1 1.4164 . . yes S1 O2 1.4331 . . yes S1 N1 1.5645 . . yes S2 O4 1.4145 . . yes S2 N1 1.5584 . . yes S2 C1 1.8240 . . yes S2 O3 1.4254 . . yes S3 C4 1.8233 . . yes S3 O6 1.4251 . . yes S3 O5 1.4284 . . yes S3 N2 1.5691 . . yes S4 C3 1.8130 . . yes S4 N2 1.5624 . . yes S4 O7 1.4293 . . yes S4 O8 1.4205 . . yes F13 C5 1.3434 . . yes F14 C5 1.3017 . . yes F15 C5 1.3224 . . yes F16 C13 1.3131 . . yes F17 C13 1.3161 . . yes F18 C13 1.3084 . . yes F1 C1 1.3279 . . yes F2 C1 1.3124 . . yes F3 C1 1.3207 . . yes F4 C2 1.3151 . . yes F5 C2 1.3106 . . yes F6 C2 1.3135 . . yes F7 C3 1.3207 . . yes F8 C3 1.3258 . . yes F9 C3 1.3124 . . yes F10 C4 1.3263 . . yes F11 C4 1.3149 . . yes F12 C4 1.3250 . . yes N3 C7 1.3386 . . yes N3 C8 1.3413 . . yes N3 C11 1.4856 . . yes N4 C15 1.3407 . . yes N4 C16 1.3422 . . yes N4 C19 1.5141 . . yes C5 C6 1.4982 . . no C6 C7 1.3732 . . no C6 C10 1.3745 . . no C8 C9 1.3685 . . no C9 C10 1.3836 . . no C11 C12 1.4982 . . no C7 H9 0.9500 . . no C8 H3 0.9500 . . no C9 H2 0.9500 . . no C10 H1 0.9500 . . no C11 H8 0.9900 . . no C11 H7 0.9900 . . no C12 H6 0.9800 . . no C12 H4 0.9800 . . no C12 H5 0.9800 . . no C13 C14 1.4962 . . no C14 C15 1.3649 . . no C14 C18 1.3753 . . no C16 C17 1.3588 . . no C17 C18 1.3752 . . no C19 C20 1.4764 . . no C15 H18 0.9500 . . no C16 H12 0.9500 . . no C17 H11 0.9500 . . no C18 H10 0.9500 . . no C19 H16 0.9900 . . no C19 H17 0.9900 . . no C20 H15 0.9800 . . no C20 H14 0.9800 . . no C20 H13 0.9800 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 S1 C2 99.29 . . . yes O1 S1 C2 103.97 . . . yes O1 S1 O2 117.11 . . . yes O1 S1 N1 111.02 . . . yes O2 S1 N1 116.91 . . . yes O2 S1 C2 105.80 . . . yes O3 S2 N1 108.26 . . . yes O3 S2 O4 118.48 . . . yes O4 S2 C1 104.89 . . . yes O3 S2 C1 104.23 . . . yes O4 S2 N1 116.56 . . . yes N1 S2 C1 102.28 . . . yes N2 S3 C4 101.26 . . . yes O6 S3 N2 116.74 . . . yes O6 S3 C4 104.72 . . . yes O5 S3 O6 118.80 . . . yes O5 S3 N2 108.54 . . . yes O5 S3 C4 104.35 . . . yes N2 S4 C3 101.00 . . . yes O8 S4 C3 104.05 . . . yes O7 S4 N2 117.16 . . . yes O8 S4 N2 108.82 . . . yes O7 S4 O8 117.99 . . . yes O7 S4 C3 105.40 . . . yes C8 N3 C11 119.20 . . . yes C7 N3 C11 119.27 . . . yes C7 N3 C8 121.53 . . . yes C16 N4 C19 120.27 . . . yes C15 N4 C16 121.46 . . . yes C15 N4 C19 118.17 . . . yes S1 N1 S2 126.79 . . . yes S3 N2 S4 126.19 . . . yes F14 C5 C6 113.64 . . . yes F15 C5 C6 110.60 . . . yes F13 C5 F14 106.36 . . . yes F13 C5 F15 108.45 . . . yes F13 C5 C6 109.41 . . . yes F14 C5 F15 108.18 . . . yes C7 C6 C10 120.61 . . . no C5 C6 C7 118.13 . . . no C5 C6 C10 121.26 . . . no N3 C7 C6 119.23 . . . yes N3 C8 C9 120.73 . . . yes C8 C9 C10 119.07 . . . no C6 C10 C9 118.82 . . . no N3 C11 C12 110.68 . . . yes C6 C7 H9 120.00 . . . no N3 C7 H9 120.00 . . . no C9 C8 H3 120.00 . . . no N3 C8 H3 120.00 . . . no C8 C9 H2 121.00 . . . no C10 C9 H2 120.00 . . . no C9 C10 H1 121.00 . . . no C6 C10 H1 121.00 . . . no N3 C11 H8 109.00 . . . no N3 C11 H7 109.00 . . . no H7 C11 H8 108.00 . . . no C12 C11 H7 110.00 . . . no C12 C11 H8 109.00 . . . no C11 C12 H6 109.00 . . . no C11 C12 H4 109.00 . . . no H4 C12 H5 109.00 . . . no C11 C12 H5 110.00 . . . no H4 C12 H6 109.00 . . . no H5 C12 H6 109.00 . . . no F16 C13 F17 106.74 . . . yes F18 C13 C14 112.56 . . . yes F16 C13 F18 106.08 . . . yes F16 C13 C14 112.08 . . . yes F17 C13 C14 111.88 . . . yes F17 C13 F18 107.09 . . . yes C13 C14 C18 120.86 . . . no C13 C14 C15 118.93 . . . no C15 C14 C18 120.20 . . . no N4 C15 C14 119.34 . . . yes N4 C16 C17 120.46 . . . yes C16 C17 C18 119.35 . . . no C14 C18 C17 119.13 . . . no N4 C19 C20 107.44 . . . yes N4 C15 H18 120.00 . . . no C14 C15 H18 120.00 . . . no C17 C16 H12 120.00 . . . no N4 C16 H12 120.00 . . . no C16 C17 H11 120.00 . . . no C18 C17 H11 120.00 . . . no C14 C18 H10 120.00 . . . no C17 C18 H10 120.00 . . . no H16 C19 H17 109.00 . . . no N4 C19 H17 110.00 . . . no C20 C19 H16 110.00 . . . no C20 C19 H17 110.00 . . . no N4 C19 H16 110.00 . . . no H13 C20 H14 110.00 . . . no H13 C20 H15 110.00 . . . no H14 C20 H15 109.00 . . . no C19 C20 H14 109.00 . . . no C19 C20 H15 109.00 . . . no C19 C20 H13 109.00 . . . no S2 C1 F3 110.78 . . . yes F1 C1 F2 108.96 . . . yes S2 C1 F1 110.19 . . . yes S2 C1 F2 111.04 . . . yes F2 C1 F3 108.36 . . . yes F1 C1 F3 107.42 . . . yes F5 C2 F6 108.88 . . . yes F4 C2 F6 108.38 . . . yes S1 C2 F4 111.03 . . . yes S1 C2 F5 109.22 . . . yes S1 C2 F6 110.83 . . . yes F4 C2 F5 108.44 . . . yes S4 C3 F7 111.38 . . . yes S4 C3 F8 110.23 . . . yes S4 C3 F9 110.49 . . . yes F7 C3 F8 108.08 . . . yes F7 C3 F9 108.10 . . . yes F8 C3 F9 108.46 . . . yes S3 C4 F10 110.45 . . . yes S3 C4 F11 112.38 . . . yes S3 C4 F12 109.83 . . . yes F10 C4 F11 107.00 . . . yes F10 C4 F12 108.37 . . . yes F11 C4 F12 108.68 . . . yes loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 S1 N1 S2 127.69 . . . . no O1 S1 C2 F5 60.32 . . . . no O2 S1 C2 F5 -63.62 . . . . no N1 S1 C2 F5 174.86 . . . . no O1 S1 C2 F6 -59.63 . . . . no O1 S1 N1 S2 -123.35 . . . . no O2 S1 N1 S2 14.59 . . . . no O2 S1 C2 F4 55.92 . . . . no N1 S1 C2 F4 -65.60 . . . . no O2 S1 C2 F6 176.43 . . . . no N1 S1 C2 F6 54.91 . . . . no O1 S1 C2 F4 179.86 . . . . no O3 S2 C1 F3 -176.44 . . . . no O4 S2 C1 F3 58.36 . . . . no N1 S2 C1 F3 -63.74 . . . . no N1 S2 C1 F2 175.80 . . . . no O3 S2 N1 S1 -166.82 . . . . no O4 S2 C1 F2 -62.10 . . . . no C1 S2 N1 S1 83.51 . . . . no O3 S2 C1 F1 -57.72 . . . . no O4 S2 N1 S1 -30.25 . . . . no O3 S2 C1 F2 63.10 . . . . no N1 S2 C1 F1 54.98 . . . . no O4 S2 C1 F1 177.09 . . . . no O5 S3 C4 F11 -61.68 . . . . no C4 S3 N2 S4 94.96 . . . . no O5 S3 C4 F12 59.43 . . . . no O6 S3 C4 F11 172.77 . . . . no N2 S3 C4 F11 50.99 . . . . no O5 S3 N2 S4 -155.58 . . . . no O6 S3 N2 S4 -18.03 . . . . no N2 S3 C4 F10 -68.41 . . . . no O6 S3 C4 F12 -66.11 . . . . no N2 S3 C4 F12 172.11 . . . . no O6 S3 C4 F10 53.37 . . . . no O5 S3 C4 F10 178.91 . . . . no C3 S4 N2 S3 104.15 . . . . no O7 S4 C3 F7 -178.23 . . . . no O8 S4 N2 S3 -146.73 . . . . no N2 S4 C3 F8 -60.60 . . . . no O8 S4 C3 F7 -53.43 . . . . no O8 S4 C3 F9 66.74 . . . . no N2 S4 C3 F9 179.53 . . . . no O7 S4 C3 F9 -58.06 . . . . no O7 S4 C3 F8 61.81 . . . . no O8 S4 C3 F8 -173.40 . . . . no O7 S4 N2 S3 -9.67 . . . . no N2 S4 C3 F7 59.36 . . . . no C11 N3 C8 C9 179.80 . . . . no C7 N3 C11 C12 -99.55 . . . . no C8 N3 C11 C12 80.21 . . . . no C11 N3 C7 C6 -179.39 . . . . no C7 N3 C8 C9 -0.44 . . . . no C8 N3 C7 C6 0.85 . . . . no C15 N4 C16 C17 -2.53 . . . . no C19 N4 C16 C17 173.90 . . . . no C16 N4 C19 C20 88.18 . . . . no C15 N4 C19 C20 -95.27 . . . . no C19 N4 C15 C14 -174.14 . . . . no C16 N4 C15 C14 2.37 . . . . no F15 C5 C6 C7 107.39 . . . . no F13 C5 C6 C10 46.12 . . . . no F13 C5 C6 C7 -133.22 . . . . no F14 C5 C6 C10 164.82 . . . . no F15 C5 C6 C10 -73.28 . . . . no F14 C5 C6 C7 -14.51 . . . . no C5 C6 C10 C9 -179.37 . . . . no C10 C6 C7 N3 -0.60 . . . . no C5 C6 C7 N3 178.74 . . . . no C7 C6 C10 C9 -0.04 . . . . no N3 C8 C9 C10 -0.22 . . . . no C8 C9 C10 C6 0.45 . . . . no F17 C13 C14 C18 35.02 . . . . no F18 C13 C14 C15 93.52 . . . . no F17 C13 C14 C15 -145.82 . . . . no F16 C13 C14 C15 -25.97 . . . . no F18 C13 C14 C18 -85.63 . . . . no F16 C13 C14 C18 154.88 . . . . no C18 C14 C15 N4 -0.59 . . . . no C13 C14 C18 C17 178.15 . . . . no C13 C14 C15 N4 -179.75 . . . . no C15 C14 C18 C17 -0.99 . . . . no N4 C16 C17 C18 0.87 . . . . no C16 C17 C18 C14 0.85 . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag S1 F3 3.3048 . . no F1 F9 3.0055 . . no F1 O3 2.9247 . . no F1 F8 3.0330 . 2_666 no F1 N1 2.9199 . . no F1 F7 2.8983 . . no F2 O3 2.9794 . . no F2 F18 3.0988 . 2_666 no F2 F8 3.0899 . 2_666 no F2 O4 2.9783 . . no F3 O4 2.9457 . . no F3 S1 3.3048 . . no F3 F16 3.0141 . 1_655 no F3 N1 3.0108 . . no F4 O2 2.9486 . . no F4 C20 3.2577 . 1_655 no F4 F11 3.0467 . 2_656 no F4 F6 3.1102 . 2_655 no F4 N1 2.9648 . . no F5 O2 2.9806 . . no F5 F17 3.0123 . 2_665 no F5 O1 2.9073 . . no F6 N1 2.8553 . . no F6 F6 3.1013 . 2_655 no F6 F11 2.8201 . 1_554 no F6 F4 3.1102 . 2_655 no F6 O1 2.9312 . . no F7 F7 2.9481 . 2_666 no F7 O8 2.8912 . . no F7 F1 2.8983 . . no F7 N2 2.9435 . . no F8 F1 3.0330 . 2_666 no F8 C12 3.2825 . 1_455 no F8 C1 3.3614 . 2_666 no F8 O7 2.9756 . . no F8 N2 2.9375 . . no F8 F2 3.0899 . 2_666 no F9 O7 2.9413 . . no F9 O8 2.9871 . . no F9 F1 3.0055 . . no F10 O6 2.9012 . . no F10 N2 3.0380 . . no F10 F14 2.7532 . 1_455 no F11 N2 2.8998 . . no F11 F6 2.8201 . 1_556 no F11 O5 2.9947 . . no F11 F4 3.0467 . 2_656 no F12 C20 3.2901 . 2_556 no F12 O5 2.9350 . . no F12 F15 2.9553 . 2_657 no F12 O6 3.0009 . . no F13 C16 3.1086 . 2_656 no F13 C17 3.2251 . 2_656 no F14 F10 2.7532 . 1_655 no F15 F12 2.9553 . 2_657 no F16 F3 3.0141 . 1_455 no F17 C8 3.1269 . 2_666 no F17 F5 3.0123 . 2_665 no F17 C9 3.3449 . 2_666 no F18 F2 3.0988 . 2_666 no F2 H5 2.7900 . . no F4 H15 2.8500 . 1_655 no F4 H13 2.7900 . 1_655 no F7 H10 2.7900 . 2_666 no F8 H6 2.7800 . 1_455 no F10 H8 2.7600 . 2_656 no F11 H2 2.8000 . . no F12 H14 2.8300 . 1_556 no F12 H15 2.8700 . 2_556 no F13 H1 2.6500 . . no F14 H9 2.3600 . . no F15 H13 2.7300 . 1_656 no F15 H14 2.8100 . 2_656 no F16 H18 2.4100 . . no F17 H10 2.5500 . . no F18 H4 2.6500 . 1_455 no F18 H5 2.8300 . 2_666 no O1 C17 3.1641 . . no O1 C16 3.2672 . . no O1 N4 3.0857 . 2_665 no O1 C16 3.0856 . 2_665 no O1 C17 3.3271 . 2_665 no O1 C15 3.3712 . 2_665 no O1 F5 2.9073 . . no O1 F6 2.9312 . . no O2 O4 2.9146 . . no O2 F4 2.9486 . . no O2 C15 3.2300 . 2_665 no O2 C19 3.3360 . 1_655 no O2 F5 2.9806 . . no O3 C11 3.2892 . . no O3 C10 3.1762 . 2_656 no O3 F1 2.9247 . . no O3 F2 2.9794 . . no O3 C9 3.2590 . 2_656 no O4 O2 2.9146 . . no O4 F3 2.9457 . . no O4 F2 2.9783 . . no O4 C15 3.1294 . 1_655 no O5 C19 3.3631 . 1_556 no O5 F11 2.9947 . . no O5 F12 2.9350 . . no O5 C17 3.3938 . 2_666 no O5 C18 3.2794 . 2_666 no O6 O7 2.8960 . . no O6 F12 3.0009 . . no O6 F10 2.9012 . . no O6 C7 3.1855 . 1_455 no O7 F9 2.9413 . . no O7 C7 3.1565 . 2_656 no O7 F8 2.9756 . . no O7 C11 3.3058 . 1_455 no O7 O6 2.8960 . . no O7 C11 3.3983 . 2_656 no O8 C7 3.3516 . 2_656 no O8 C8 3.1232 . 2_656 no O8 N3 3.1547 . 2_656 no O8 C9 3.2873 . 2_656 no O8 C9 3.2263 . . no O8 F9 2.9871 . . no O8 C8 3.2741 . . no O8 F7 2.8912 . . no O1 H12 2.7000 . . no O1 H11 2.4900 . . no O2 H17 2.5400 . 1_655 no O2 H18 2.5600 . 1_655 no O2 H17 2.9000 . 2_665 no O3 H3 2.6500 . . no O3 H1 2.8000 . 2_656 no O3 H8 2.4200 . . no O4 H18 2.5400 . 1_655 no O5 H16 2.5600 . 1_556 no O5 H12 2.5700 . 1_556 no O6 H9 2.5700 . 1_455 no O7 H7 2.9100 . 2_656 no O7 H7 2.4100 . 1_455 no O7 H9 2.9100 . 1_455 no O8 H3 2.6700 . . no O8 H2 2.5900 . . no N1 F6 2.8553 . . no N1 F1 2.9199 . . no N1 F3 3.0108 . . no N1 F4 2.9648 . . no N2 F7 2.9435 . . no N2 F10 3.0380 . . no N2 F11 2.8998 . . no N2 F8 2.9375 . . no N3 O8 3.1547 . 2_656 no N4 O1 3.0857 . 2_665 no N1 H1 2.7600 . 2_656 no N2 H10 2.9100 . 2_666 no C1 F8 3.3614 . 2_666 no C7 O7 3.1565 . 2_656 no C7 O8 3.3516 . 2_656 no C7 O6 3.1855 . 1_655 no C8 F17 3.1269 . 2_666 no C8 O8 3.2741 . . no C8 O8 3.1232 . 2_656 no C9 O3 3.2590 . 2_656 no C9 O8 3.2873 . 2_656 no C9 O8 3.2263 . . no C9 F17 3.3449 . 2_666 no C10 O3 3.1762 . 2_656 no C11 O3 3.2892 . . no C11 O7 3.3058 . 1_655 no C11 O7 3.3983 . 2_656 no C12 F8 3.2825 . 1_655 no C15 O1 3.3712 . 2_665 no C15 O4 3.1294 . 1_455 no C15 O2 3.2300 . 2_665 no C16 O1 3.2672 . . no C16 F13 3.1086 . 2_656 no C16 O1 3.0856 . 2_665 no C17 O1 3.1641 . . no C17 F13 3.2251 . 2_656 no C17 O1 3.3271 . 2_665 no C17 O5 3.3938 . 2_666 no C18 O5 3.2794 . 2_666 no C19 O2 3.3360 . 1_455 no C19 O5 3.3631 . 1_554 no C20 F4 3.2577 . 1_455 no C20 F12 3.2901 . 2_556 no C8 H5 2.9000 . . no C15 H15 3.0000 . . no C16 H14 2.9600 . . no H1 O3 2.8000 . 2_656 no H1 F13 2.6500 . . no H1 N1 2.7600 . 2_656 no H2 O8 2.5900 . . no H2 F11 2.8000 . . no H3 O3 2.6500 . . no H3 O8 2.6700 . . no H3 H8 2.4300 . . no H4 F18 2.6500 . 1_655 no H5 F2 2.7900 . . no H5 C8 2.9000 . . no H5 F18 2.8300 . 2_666 no H6 F8 2.7800 . 1_655 no H7 H9 2.3100 . . no H7 O7 2.9100 . 2_656 no H7 O7 2.4100 . 1_655 no H8 H3 2.4300 . . no H8 O3 2.4200 . . no H8 F10 2.7600 . 2_656 no H9 H7 2.3100 . . no H9 F14 2.3600 . . no H9 O7 2.9100 . 1_655 no H9 O6 2.5700 . 1_655 no H10 F7 2.7900 . 2_666 no H10 F17 2.5500 . . no H10 N2 2.9100 . 2_666 no H11 O1 2.4900 . . no H12 O1 2.7000 . . no H12 O5 2.5700 . 1_554 no H12 H16 2.4500 . . no H13 F15 2.7300 . 1_454 no H13 F4 2.7900 . 1_455 no H14 C16 2.9600 . . no H14 F15 2.8100 . 2_656 no H14 F12 2.8300 . 1_554 no H15 F12 2.8700 . 2_556 no H15 F4 2.8500 . 1_455 no H15 C15 3.0000 . . no H16 H12 2.4500 . . no H16 O5 2.5600 . 1_554 no H17 O2 2.9000 . 2_665 no H17 O2 2.5400 . 1_455 no H17 H18 2.3500 . . no H18 H17 2.3500 . . no H18 F16 2.4100 . . no H18 O2 2.5600 . 1_455 no H18 O4 2.5400 . 1_455 no #===END #===END data_2 _database_code_depnum_ccdc_archive 'CCDC 690235' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-Methyl-4-cyanopyridinium bis{(trifluoromethyl)sulfonyl}amide ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H7 F6 N3 O4 S2' _chemical_formula_weight 399.30 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' 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 11.4431(11) _cell_length_b 11.8766(11) _cell_length_c 12.1955(11) _cell_angle_alpha 90.00 _cell_angle_beta 114.779(2) _cell_angle_gamma 90.00 _cell_volume 1504.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.762 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.444 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8971 _exptl_absorpt_correction_T_max 0.9781 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.77490 _diffrn_radiation_type 'synchrotron radiation' _diffrn_radiation_source 'advanced light source station 11.3.1' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker Platinum 200 CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9483 _diffrn_reflns_av_R_equivalents 0.0708 _diffrn_reflns_av_sigmaI/netI 0.0755 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2032 _reflns_number_gt 1916 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT v7.34a' _computing_data_reduction 'Bruker SAINT v7.34a' _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 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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment geom _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.065(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2032 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1064 _refine_ls_R_factor_gt 0.0990 _refine_ls_wR_factor_ref 0.3582 _refine_ls_wR_factor_gt 0.3419 _refine_ls_goodness_of_fit_ref 1.782 _refine_ls_restrained_S_all 1.782 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.981 _refine_diff_density_min -0.812 _refine_diff_density_rms 0.207 loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags N2 N Uani 0.58350 0.06290 0.29730 1.000 0.0383 . . N3 N Uani 0.83610 0.44870 0.44310 1.000 0.0577 . . C3 C Uani 0.59160 0.13360 0.21480 1.000 0.0414 . . C4 C Uani 0.65750 0.23320 0.24950 1.000 0.0448 . . C5 C Uani 0.71340 0.25840 0.37080 1.000 0.0343 . . C6 C Uani 0.78200 0.36520 0.41060 1.000 0.0425 . . C7 C Uani 0.70480 0.18740 0.45480 1.000 0.0382 . . C8 C Uani 0.63750 0.08800 0.41410 1.000 0.0381 . . C9 C Uani 0.51100 -0.04340 0.25880 1.000 0.0521 . . S1 S Uani 0.30584 0.21208 0.34653 1.000 0.0448 . . S2 S Uani 0.10777 0.16478 0.41466 1.000 0.0502 . . F1 F Uani 0.00090 -0.02970 0.39310 1.000 0.2075 . . F2 F Uani -0.04690 0.05100 0.22740 1.000 0.1963 . . F3 F Uani 0.12550 -0.02120 0.31220 1.000 0.1603 . . F4 F Uani 0.37860 0.32120 0.54840 1.000 0.1400 . . F5 F Uani 0.49700 0.34650 0.45340 1.000 0.1131 . . F6 F Uani 0.32060 0.42700 0.39470 1.000 0.1142 . . O1 O Uani 0.31460 0.23360 0.23710 1.000 0.0799 . . O2 O Uani 0.37720 0.11930 0.41540 1.000 0.0638 . . O3 O Uani 0.00450 0.22890 0.41460 1.000 0.1062 . . O4 O Uani 0.19880 0.12500 0.52680 1.000 0.0518 . . N1 N Uani 0.16360 0.22150 0.33040 1.000 0.0542 . . C1 C Uani 0.03450 0.03450 0.33300 1.000 0.0887 . . C2 C Uani 0.37840 0.33430 0.44020 1.000 0.0727 . . H1 H Uiso 0.62970 0.03690 0.47060 1.000 0.0457 . . H2 H Uiso 0.74370 0.20550 0.53840 1.000 0.0458 . . H3 H Uiso 0.66440 0.28320 0.19170 1.000 0.0537 . . H4 H Uiso 0.55120 0.11440 0.13160 1.000 0.0497 . . H5 H Uiso 0.56370 -0.10580 0.30680 1.000 0.0781 . . H6 H Uiso 0.48950 -0.05660 0.17310 1.000 0.0781 . . H7 H Uiso 0.43170 -0.03840 0.27070 1.000 0.0781 . . 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 N2 0.0313 0.0390 0.0410 0.0006 0.0116 0.0063 N3 0.0510 0.0470 0.0740 -0.0050 0.0250 -0.0060 C3 0.0420 0.0470 0.0340 0.0029 0.0147 0.0010 C4 0.0470 0.0430 0.0450 0.0075 0.0200 0.0013 C5 0.0260 0.0330 0.0410 -0.0002 0.0113 0.0007 C6 0.0350 0.0480 0.0440 0.0020 0.0160 0.0010 C7 0.0350 0.0420 0.0340 0.0000 0.0110 0.0027 C8 0.0370 0.0400 0.0370 0.0070 0.0152 0.0050 C9 0.0470 0.0470 0.0590 -0.0050 0.0190 -0.0070 S1 0.0506 0.0473 0.0442 0.0075 0.0273 0.0041 S2 0.0403 0.0464 0.0689 0.0101 0.0279 0.0058 F1 0.3490 0.1630 0.1320 -0.0570 0.1220 -0.1900 F2 0.1790 0.1750 0.1170 0.0340 -0.0540 -0.0970 F3 0.2670 0.1040 0.1310 -0.0690 0.1040 -0.0560 F4 0.1810 0.1550 0.0910 -0.0640 0.0640 -0.0630 F5 0.0480 0.0990 0.1820 -0.0320 0.0380 -0.0106 F6 0.0720 0.0500 0.2220 -0.0230 0.0630 -0.0002 O1 0.1100 0.0830 0.0620 0.0120 0.0510 -0.0040 O2 0.0630 0.0590 0.0880 0.0262 0.0500 0.0197 O3 0.0740 0.0690 0.2030 0.0360 0.0850 0.0280 O4 0.0570 0.0600 0.0437 0.0060 0.0263 0.0058 N1 0.0520 0.0560 0.0510 0.0187 0.0180 0.0028 C1 0.1190 0.0820 0.0570 0.0060 0.0290 -0.0400 C2 0.0540 0.0710 0.0950 -0.0120 0.0330 -0.0040 _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 N1 1.5595 . . yes S1 O1 1.4030 . . yes S1 O2 1.4183 . . yes S1 C2 1.8183 . . yes S2 N1 1.5710 . . yes S2 O3 1.4056 . . yes S2 O4 1.4087 . . yes S2 C1 1.8409 . . yes F1 C1 1.2258 . . yes F2 C1 1.2486 . . yes F3 C1 1.3445 . . yes F4 C2 1.3277 . . yes F5 C2 1.3060 . . yes F6 C2 1.2845 . . yes N2 C3 1.3432 . . yes N2 C8 1.3274 . . yes N2 C9 1.4752 . . yes N3 C6 1.1481 . . yes C3 C4 1.3710 . . no C4 C5 1.3762 . . no C5 C7 1.3619 . . no C5 C6 1.4633 . . no C7 C8 1.3830 . . no C3 H4 0.9500 . . no C4 H3 0.9500 . . no C7 H2 0.9500 . . no C8 H1 0.9500 . . no C9 H7 0.9800 . . no C9 H5 0.9800 . . no C9 H6 0.9800 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 S1 C2 101.51 . . . yes O1 S1 N1 110.72 . . . yes O1 S1 C2 104.85 . . . yes O1 S1 O2 116.86 . . . yes O2 S1 C2 104.49 . . . yes O2 S1 N1 116.22 . . . yes O3 S2 C1 105.24 . . . yes O3 S2 N1 109.85 . . . yes O3 S2 O4 117.49 . . . yes N1 S2 C1 102.97 . . . yes O4 S2 N1 116.16 . . . yes O4 S2 C1 103.13 . . . yes C3 N2 C8 121.08 . . . yes C3 N2 C9 120.18 . . . yes C8 N2 C9 118.72 . . . yes S1 N1 S2 125.15 . . . yes N2 C3 C4 120.66 . . . yes C3 C4 C5 117.85 . . . no C4 C5 C7 121.76 . . . no C6 C5 C7 119.02 . . . no C4 C5 C6 119.22 . . . no N3 C6 C5 179.26 . . . yes C5 C7 C8 117.61 . . . no N2 C8 C7 121.04 . . . yes N2 C3 H4 120.00 . . . no C4 C3 H4 120.00 . . . no C5 C4 H3 121.00 . . . no C3 C4 H3 121.00 . . . no C8 C7 H2 121.00 . . . no C5 C7 H2 121.00 . . . no C7 C8 H1 120.00 . . . no N2 C8 H1 119.00 . . . no H6 C9 H7 109.00 . . . no H5 C9 H7 110.00 . . . no N2 C9 H5 110.00 . . . no N2 C9 H6 109.00 . . . no N2 C9 H7 109.00 . . . no H5 C9 H6 109.00 . . . no S2 C1 F1 112.66 . . . yes S2 C1 F2 113.57 . . . yes S2 C1 F3 107.61 . . . yes F1 C1 F2 115.40 . . . yes F1 C1 F3 105.58 . . . yes F2 C1 F3 100.64 . . . yes S1 C2 F4 109.93 . . . yes S1 C2 F5 110.08 . . . yes S1 C2 F6 113.33 . . . yes F4 C2 F5 108.76 . . . yes F4 C2 F6 108.41 . . . yes F5 C2 F6 106.17 . . . yes 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 O1 S1 C2 F6 60.33 . . . . no O2 S1 C2 F6 -176.21 . . . . no N1 S1 C2 F6 -54.99 . . . . no O1 S1 N1 S2 157.65 . . . . no O2 S1 N1 S2 21.19 . . . . no C2 S1 N1 S2 -91.45 . . . . no O1 S1 C2 F5 -58.39 . . . . no O2 S1 C2 F5 65.07 . . . . no N1 S1 C2 F5 -173.71 . . . . no O2 S1 C2 F4 -54.72 . . . . no N1 S1 C2 F4 66.50 . . . . no O1 S1 C2 F4 -178.19 . . . . no N1 S2 C1 F3 54.47 . . . . no N1 S2 C1 F1 170.44 . . . . no O3 S2 C1 F3 169.56 . . . . no O4 S2 C1 F3 -66.74 . . . . no O3 S2 C1 F1 -74.48 . . . . no O4 S2 C1 F1 49.22 . . . . no O3 S2 C1 F2 59.09 . . . . no O4 S2 C1 F2 -177.21 . . . . no N1 S2 C1 F2 -55.99 . . . . no O3 S2 N1 S1 151.56 . . . . no O4 S2 N1 S1 15.16 . . . . no C1 S2 N1 S1 -96.73 . . . . no C9 N2 C8 C7 -178.98 . . . . no C9 N2 C3 C4 179.25 . . . . no C3 N2 C8 C7 -0.53 . . . . no C8 N2 C3 C4 0.83 . . . . no N2 C3 C4 C5 -0.67 . . . . no C3 C4 C5 C7 0.24 . . . . no C3 C4 C5 C6 -178.65 . . . . no C6 C5 C7 C8 178.94 . . . . no C4 C5 C7 C8 0.05 . . . . no C5 C7 C8 N2 0.09 . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag S1 F3 3.3743 . . no S2 F4 3.3881 . . no F1 O4 3.0543 . 3_556 no F1 O3 3.0813 . . no F1 O4 2.8403 . . no F1 F1 2.7095 . 3_556 no F2 N1 2.9907 . . no F2 O3 2.9827 . . no F2 C6 3.3383 . 2_545 no F2 F4 2.4972 . 4_454 no F3 O2 3.1025 . . no F3 S1 3.3743 . . no F3 C7 3.3341 . 3_656 no F3 O4 2.9543 . . no F3 N1 2.9098 . . no F3 F6 2.9035 . 2_545 no F3 O1 3.1076 . 2_545 no F4 S2 3.3881 . . no F4 F2 2.4972 . 4_555 no F4 O4 3.0460 . . no F4 N1 3.0067 . . no F4 O2 2.8912 . . no F5 C7 3.0317 . . no F5 C5 3.2144 . . no F5 O1 2.9151 . . no F5 O2 2.9737 . . no F6 N1 2.9357 . . no F6 O1 2.9773 . . no F6 F3 2.9035 . 2_555 no F1 H3 2.8200 . 2_545 no F3 H2 2.8400 . 3_656 no F6 H7 2.7700 . 2_555 no O1 F5 2.9151 . . no O1 F6 2.9773 . . no O1 F3 3.1076 . 2_555 no O1 C7 3.2689 . 4_454 no O2 C8 3.2721 . 3_656 no O2 F3 3.1025 . . no O2 F4 2.8912 . . no O2 O4 2.8884 . . no O2 C8 3.0084 . . no O2 F5 2.9737 . . no O3 C5 3.1643 . 1_455 no O3 C6 3.0002 . 1_455 no O3 F2 2.9827 . . no O3 F1 3.0813 . . no O3 C9 3.3915 . 2_555 no O4 C4 3.3929 . 4_455 no O4 C9 3.3949 . 3_656 no O4 F1 2.8403 . . no O4 F3 2.9543 . . no O4 F1 3.0543 . 3_556 no O4 C8 3.0490 . 3_656 no O4 O2 2.8884 . . no O4 F4 3.0460 . . no O1 H2 2.3200 . 4_454 no O2 H7 2.8200 . . no O2 H1 2.8500 . . no O2 H1 2.3400 . 3_656 no O3 H6 2.7700 . 2_555 no O4 H1 2.7400 . 3_656 no O4 H3 2.4600 . 4_455 no O4 H5 2.6300 . 3_656 no N1 F4 3.0067 . . no N1 F2 2.9907 . . no N1 F3 2.9098 . . no N1 F6 2.9357 . . no N1 C9 3.3391 . 2_555 no N3 C3 3.2482 . 2_655 no N3 H6 2.8900 . 2_655 no N3 H4 2.6800 . 4_555 no N3 H4 2.7100 . 2_655 no N3 H6 2.9100 . 4_555 no C3 N3 3.2482 . 2_645 no C4 O4 3.3929 . 4_554 no C5 F5 3.2144 . . no C5 O3 3.1643 . 1_655 no C6 F2 3.3383 . 2_555 no C6 O3 3.0002 . 1_655 no C7 O1 3.2689 . 4_555 no C7 F3 3.3341 . 3_656 no C7 F5 3.0317 . . no C8 O2 3.2721 . 3_656 no C8 O4 3.0490 . 3_656 no C8 O2 3.0084 . . no C9 N1 3.3391 . 2_545 no C9 O4 3.3949 . 3_656 no C9 O3 3.3915 . 2_545 no H1 O2 2.3400 . 3_656 no H1 O4 2.7400 . 3_656 no H1 O2 2.8500 . . no H1 H5 2.4800 . . no H2 F3 2.8400 . 3_656 no H2 O1 2.3200 . 4_555 no H3 F1 2.8200 . 2_555 no H3 O4 2.4600 . 4_554 no H4 N3 2.6800 . 4_454 no H4 N3 2.7100 . 2_645 no H4 H6 2.2800 . . no H5 H1 2.4800 . . no H5 O4 2.6300 . 3_656 no H6 H4 2.2800 . . no H6 O3 2.7700 . 2_545 no H6 N3 2.9100 . 4_454 no H6 N3 2.8900 . 2_645 no H7 F6 2.7700 . 2_545 no H7 O2 2.8200 . . no #===END data_4 _database_code_depnum_ccdc_archive 'CCDC 690236' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-Ethyl-4-cyanopyridinium bis{(trifluoromethyl)sulfonyl}amide ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H10 F6 N3 O4 S2' _chemical_formula_weight 414.33 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' 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 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 9.7224(12) _cell_length_b 10.7874(14) _cell_length_c 16.190(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.573(2) _cell_angle_gamma 90.00 _cell_volume 1650.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.667 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 836 _exptl_absorpt_coefficient_mu 0.408 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9413 _exptl_absorpt_correction_T_max 0.9604 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.77490 _diffrn_radiation_type 'synchrotron radiation' _diffrn_radiation_source 'advanced light source station 11.3.1' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker Platinum 200 CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11460 _diffrn_reflns_av_R_equivalents 0.0644 _diffrn_reflns_av_sigmaI/netI 0.0849 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 33.66 _reflns_number_total 4950 _reflns_number_gt 4268 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT v7.34a' _computing_data_reduction 'Bruker SAINT v7.34a' _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 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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment geom _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.04(17) _refine_ls_number_reflns 4950 _refine_ls_number_parameters 215 _refine_ls_number_restraints 70 _refine_ls_R_factor_all 0.1203 _refine_ls_R_factor_gt 0.1118 _refine_ls_wR_factor_ref 0.3166 _refine_ls_wR_factor_gt 0.3035 _refine_ls_goodness_of_fit_ref 1.275 _refine_ls_restrained_S_all 1.370 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 33.66 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.755 _refine_diff_density_min -0.749 _refine_diff_density_rms 0.161 loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags S1 S Uani 0.79674 0.11023 0.26013 0.600 0.0518 . . S2 S Uani 0.53763 0.13680 0.14076 0.600 0.0557 . . F1 F Uiso 0.49910 0.11510 -0.02170 0.600 0.0940 . . F2 F Uiso 0.67590 0.23540 0.03930 0.600 0.1030 . . F3 F Uiso 0.70070 0.04760 0.05010 0.600 0.0810 . . F4 F Uiso 0.84820 0.02230 0.41360 0.600 0.0743 . . F5 F Uiso 0.62820 0.02560 0.35190 0.600 0.0910 . . F6 F Uiso 0.72010 0.19110 0.39440 0.600 0.0970 . . O1 O Uiso 0.81490 -0.00770 0.22870 0.600 0.0585 . . O2 O Uiso 0.92470 0.18620 0.28590 0.600 0.0640 . . O3 O Uiso 0.43930 0.23700 0.12600 0.600 0.0554 . . O4 O Uiso 0.50270 0.01890 0.15470 0.600 0.0591 . . N1 N Uiso 0.67430 0.19340 0.20890 0.600 0.0407 . . C1 C Uani 0.60060 0.13930 0.04560 0.600 0.0876 . . C2 C Uani 0.74470 0.08030 0.35900 0.600 0.0754 . . S3 S Uani 0.79674 0.11023 0.26013 0.400 0.0518 . . S4 S Uani 0.53763 0.13680 0.14076 0.400 0.0557 . . F7 F Uiso 0.72970 0.09110 0.04770 0.400 0.0810 . . F8 F Uiso 0.53500 0.06900 -0.01420 0.400 0.1240 . . F9 F Uiso 0.62810 0.25650 0.02690 0.400 0.0790 . . F10 F Uiso 0.67120 -0.03310 0.34830 0.400 0.1000 . . F11 F Uiso 0.85520 0.07840 0.42210 0.400 0.0760 . . F12 F Uiso 0.65010 0.15050 0.37250 0.400 0.0950 . . O5 O Uiso 0.87100 0.01100 0.24040 0.400 0.1060 . . O6 O Uiso 0.90200 0.21200 0.28980 0.400 0.0920 . . O7 O Uiso 0.50400 0.23400 0.18050 0.400 0.0930 . . O8 O Uiso 0.40600 0.03400 0.11620 0.400 0.1060 . . N2 N Uiso 0.64900 0.03700 0.18460 0.400 0.0740 . . C3 C Uani 0.60060 0.13930 0.04560 0.400 0.0876 . . C4 C Uani 0.74470 0.08030 0.35900 0.400 0.0754 . . N3 N Uani 0.21190 0.06400 0.24630 1.000 0.0448 . . N4 N Uani -0.06580 0.26210 -0.04500 1.000 0.0915 . . C5 C Uani 0.21390 0.18630 0.23930 1.000 0.0597 . . C6 C Uani 0.14250 0.24320 0.16450 1.000 0.0627 . . C7 C Uani 0.06970 0.16900 0.09890 1.000 0.0495 . . C8 C Uani -0.00560 0.22270 0.01970 1.000 0.0695 . . C9 C Uani 0.06540 0.04260 0.11030 1.000 0.0590 . . C10 C Uani 0.14040 -0.00750 0.18580 1.000 0.0598 . . C11 C Uani 0.28710 0.00530 0.32860 1.000 0.0567 . . C12 C Uani 0.18700 -0.00910 0.38550 1.000 0.0781 . . H1 H Uiso 0.14030 -0.09470 0.19410 1.000 0.0718 . . H2 H Uiso 0.01180 -0.00900 0.06690 1.000 0.0708 . . H3 H Uiso 0.14360 0.33080 0.15860 1.000 0.0752 . . H4 H Uiso 0.26410 0.23510 0.28550 1.000 0.0716 . . H5 H Uiso 0.23690 -0.04620 0.43950 1.000 0.1171 . . H6 H Uiso 0.10820 -0.06280 0.35810 1.000 0.1171 . . H7 H Uiso 0.15020 0.07250 0.39630 1.000 0.1171 . . H8 H Uiso 0.32410 -0.07690 0.31740 1.000 0.0680 . . H9 H Uiso 0.36810 0.05770 0.35680 1.000 0.0680 . . 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 0.0498 0.0541 0.0546 0.0111 0.0187 0.0102 S2 0.0488 0.0564 0.0628 -0.0001 0.0149 0.0110 C1 0.1040 0.1130 0.0470 -0.0130 0.0200 -0.0180 C2 0.0590 0.1150 0.0550 0.0300 0.0190 0.0120 S3 0.0498 0.0541 0.0546 0.0111 0.0187 0.0102 S4 0.0488 0.0564 0.0628 -0.0001 0.0149 0.0110 C3 0.1040 0.1130 0.0470 -0.0130 0.0200 -0.0180 C4 0.0590 0.1150 0.0550 0.0300 0.0190 0.0120 N3 0.0427 0.0380 0.0530 -0.0092 0.0095 -0.0023 N4 0.0760 0.1080 0.0870 0.0540 0.0120 0.0010 C5 0.0660 0.0340 0.0800 -0.0130 0.0190 -0.0094 C6 0.0700 0.0370 0.0830 -0.0020 0.0220 0.0030 C7 0.0500 0.0430 0.0600 0.0060 0.0220 0.0016 C8 0.0770 0.0630 0.0770 0.0180 0.0350 0.0090 C9 0.0800 0.0420 0.0490 0.0001 0.0030 -0.0010 C10 0.0690 0.0344 0.0620 0.0015 -0.0130 -0.0064 C11 0.0510 0.0590 0.0530 -0.0080 -0.0020 0.0090 C12 0.0590 0.1000 0.0730 0.0230 0.0110 0.0060 _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.3967 . . yes S1 O2 1.4662 . . yes S1 N1 1.5641 . . yes S1 C2 1.8173 . . yes S2 O3 1.4255 . . yes S2 O4 1.3490 . . yes S2 N1 1.6332 . . yes S2 C1 1.7866 . . yes S3 O6 1.5009 . . yes S3 N2 1.8325 . . yes S3 C4 1.8173 . . yes S3 O5 1.3702 . . yes S4 O8 1.6694 . . yes S4 N2 1.5731 . . yes S4 O7 1.3111 . . yes S4 C3 1.7866 . . yes F1 C1 1.3132 . . yes F2 C1 1.2869 . . yes F3 C1 1.3776 . . yes F4 C2 1.3296 . . yes F5 C2 1.2583 . . yes F6 C2 1.3706 . . yes F7 C3 1.3516 . . yes F8 C3 1.2765 . . yes F9 C3 1.3415 . . yes F10 C4 1.4068 . . yes F11 C4 1.2973 . . yes F12 C4 1.2496 . . yes N3 C5 1.3247 . . yes N3 C10 1.3107 . . yes N3 C11 1.5012 . . yes N4 C8 1.1544 . . yes C5 C6 1.3895 . . no C6 C7 1.3845 . . no C7 C8 1.4405 . . no C7 C9 1.3779 . . no C9 C10 1.3782 . . no C11 C12 1.4969 . . no C5 H4 0.9500 . . no C6 H3 0.9500 . . no C9 H2 0.9500 . . no C10 H1 0.9500 . . no C11 H8 0.9900 . . no C11 H9 0.9900 . . no C12 H5 0.9800 . . no C12 H6 0.9800 . . no C12 H7 0.9800 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 O2 116.19 . . . yes O1 S1 N1 118.35 . . . yes O1 S1 C2 104.14 . . . yes O2 S1 N1 108.64 . . . yes O2 S1 C2 103.99 . . . yes N1 S1 C2 103.56 . . . yes O3 S2 O4 123.89 . . . yes O3 S2 N1 103.71 . . . yes O3 S2 C1 101.31 . . . yes O4 S2 N1 115.87 . . . yes O4 S2 C1 108.01 . . . yes N1 S2 C1 100.82 . . . yes O5 S3 C4 109.72 . . . yes O6 S3 N2 153.86 . . . yes O6 S3 C4 99.09 . . . yes N2 S3 C4 100.05 . . . yes O5 S3 N2 83.17 . . . yes O5 S3 O6 106.80 . . . yes O7 S4 N2 123.40 . . . yes O7 S4 O8 112.50 . . . yes O8 S4 C3 101.73 . . . yes N2 S4 C3 93.47 . . . yes O7 S4 C3 125.91 . . . yes O8 S4 N2 93.49 . . . yes S1 N1 S2 122.75 . . . yes S3 N2 S4 110.78 . . . yes C10 N3 C11 118.52 . . . yes C5 N3 C11 118.83 . . . yes C5 N3 C10 122.55 . . . yes F1 C1 F2 115.16 . . . yes S2 C1 F3 108.93 . . . yes F2 C1 F3 100.06 . . . yes F1 C1 F3 106.57 . . . yes S2 C1 F2 113.39 . . . yes S2 C1 F1 111.69 . . . yes F5 C2 F6 101.86 . . . yes F4 C2 F6 108.15 . . . yes F4 C2 F5 111.39 . . . yes S1 C2 F6 108.99 . . . yes S1 C2 F4 110.21 . . . yes S1 C2 F5 115.69 . . . yes S4 C3 F8 115.71 . . . yes F7 C3 F9 97.77 . . . yes S4 C3 F9 109.61 . . . yes F7 C3 F8 94.95 . . . yes S4 C3 F7 118.47 . . . yes F8 C3 F9 118.64 . . . yes S3 C4 F12 114.51 . . . yes F10 C4 F12 100.08 . . . yes F11 C4 F12 112.29 . . . yes F10 C4 F11 112.71 . . . yes S3 C4 F10 106.52 . . . yes S3 C4 F11 110.25 . . . yes N3 C5 C6 120.01 . . . yes C5 C6 C7 118.30 . . . no C6 C7 C8 120.79 . . . no C6 C7 C9 119.70 . . . no C8 C7 C9 119.48 . . . no N4 C8 C7 177.81 . . . yes C7 C9 C10 118.72 . . . no N3 C10 C9 120.63 . . . yes N3 C11 C12 109.78 . . . yes N3 C5 H4 120.00 . . . no C6 C5 H4 120.00 . . . no C5 C6 H3 121.00 . . . no C7 C6 H3 121.00 . . . no C7 C9 H2 121.00 . . . no C10 C9 H2 121.00 . . . no N3 C10 H1 120.00 . . . no C9 C10 H1 120.00 . . . no N3 C11 H8 110.00 . . . no N3 C11 H9 110.00 . . . no C12 C11 H8 110.00 . . . no C12 C11 H9 110.00 . . . no H8 C11 H9 108.00 . . . no C11 C12 H5 110.00 . . . no C11 C12 H6 110.00 . . . no C11 C12 H7 109.00 . . . no H5 C12 H6 109.00 . . . no H5 C12 H7 109.00 . . . no H6 C12 H7 109.00 . . . no 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 O1 S1 N1 S2 20.97 . . . . no O2 S1 N1 S2 156.31 . . . . no C2 S1 N1 S2 -93.59 . . . . no O1 S1 C2 F5 -64.35 . . . . no O2 S1 C2 F5 173.52 . . . . no N1 S1 C2 F5 60.01 . . . . no O1 S1 C2 F6 -178.35 . . . . no O2 S1 C2 F6 59.52 . . . . no N1 S1 C2 F6 -53.99 . . . . no O2 S1 C2 F4 -59.01 . . . . no N1 S1 C2 F4 -172.52 . . . . no O1 S1 C2 F4 63.12 . . . . no N1 S2 C1 F2 -38.05 . . . . no O4 S2 C1 F3 -49.55 . . . . no N1 S2 C1 F3 72.41 . . . . no O3 S2 C1 F3 178.92 . . . . no O3 S2 C1 F2 68.47 . . . . no O4 S2 C1 F2 -160.00 . . . . no O3 S2 N1 S1 165.94 . . . . no O4 S2 N1 S1 26.80 . . . . no C1 S2 N1 S1 -89.46 . . . . no O3 S2 C1 F1 -63.64 . . . . no O4 S2 C1 F1 67.89 . . . . no N1 S2 C1 F1 -170.15 . . . . no C10 N3 C5 C6 -2.36 . . . . no C11 N3 C5 C6 -178.56 . . . . no C11 N3 C10 C9 177.61 . . . . no C5 N3 C11 C12 91.22 . . . . no C10 N3 C11 C12 -85.13 . . . . no C5 N3 C10 C9 1.41 . . . . no N3 C5 C6 C7 0.41 . . . . no C5 C6 C7 C8 -179.65 . . . . no C5 C6 C7 C9 2.39 . . . . no C8 C7 C9 C10 178.69 . . . . no C6 C7 C9 C10 -3.33 . . . . no C7 C9 C10 N3 1.48 . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag S1 F3 3.3765 . . no S3 S2 2.8068 . . no S3 F7 3.3532 . . no S3 C1 3.5622 . . no S4 C2 3.6837 . . no S4 S1 2.8068 . . no S2 H1 3.1200 . 3_555 no S4 H1 3.1200 . 3_555 no F1 O4 3.0311 . . no F1 O3 2.9048 . . no F1 C12 3.2607 . 2_554 no F1 F5 3.0451 . 2_554 no F1 C11 3.0765 . 2_554 no F2 O3 2.9627 . . no F2 N1 2.7866 . . no F2 N4 3.1402 . 1_655 no F2 C8 3.1890 . 1_655 no F3 N1 3.0756 . . no F3 F4 2.9994 . 2_554 no F3 O1 2.9056 . . no F3 O4 2.8635 . . no F3 S1 3.3765 . . no F4 O1 2.9523 . . no F4 O2 2.9454 . . no F4 C8 3.2879 . 2_655 no F4 F3 2.9994 . 2_555 no F4 N4 3.2090 . 2_655 no F5 O1 3.0169 . . no F5 C11 3.2559 . . no F5 O4 3.1399 . . no F5 N1 3.0536 . . no F5 F1 3.0451 . 2_555 no F6 N1 2.9310 . . no F6 C12 3.2499 . 3_555 no F6 O2 2.9471 . . no F6 N4 3.1975 . 4_555 no F7 C7 3.3218 . 1_655 no F7 C9 3.2250 . 1_655 no F7 S1 3.3532 . . no F7 S2 2.7057 . . no F7 N2 2.5855 . . no F7 C8 3.0645 . 1_655 no F8 S2 2.6076 . . no F8 N2 3.1674 . . no F8 C11 3.1701 . 2_554 no F8 F10 2.8710 . 2_554 no F8 O8 2.7231 . . no F9 S2 2.5691 . . no F9 O7 3.0178 . . no F10 F8 2.8710 . 2_555 no F10 N2 2.7155 . . no F10 O5 2.9401 . . no F10 S1 2.5953 . . no F11 S1 2.5725 . . no F11 O6 2.7073 . . no F11 O5 3.0689 . . no F12 O6 3.1257 . . no F12 S1 2.5978 . . no F12 N4 2.8974 . 4_555 no F1 H9 2.7900 . 2_554 no F1 H5 2.5900 . 2_554 no F1 H8 2.7900 . 2_554 no F4 H2 2.6200 . 2_655 no F5 H9 2.5700 . . no F8 H5 2.8300 . 2_554 no F8 H9 2.7000 . 2_554 no F9 H7 2.8500 . 4_554 no F11 H2 2.5900 . 2_655 no O1 F5 3.0169 . . no O1 O4 3.0040 . . no O1 C10 3.3954 . 1_655 no O1 C6 3.2082 . 3_545 no O1 F3 2.9056 . . no O1 F4 2.9523 . . no O2 C5 3.0774 . 1_655 no O2 C12 3.4076 . 1_655 no O2 F4 2.9454 . . no O2 F6 2.9471 . . no O2 C6 3.2678 . 1_655 no O3 C10 3.3865 . 3_555 no O3 C5 3.2176 . . no O3 F2 2.9627 . . no O3 C6 3.0926 . . no O3 F1 2.9048 . . no O4 F3 2.8635 . . no O4 F1 3.0311 . . no O4 O1 3.0040 . . no O4 C6 3.2583 . 3_545 no O4 F5 3.1399 . . no O5 C12 3.4084 . 1_655 no O5 F10 2.9401 . . no O5 C9 3.1613 . 1_655 no O5 C2 2.6192 . . no O5 F11 3.0689 . . no O5 C10 2.9611 . 1_655 no O6 F12 3.1257 . . no O6 F11 2.7073 . . no O6 C2 2.5331 . . no O6 C5 3.3324 . 1_655 no O7 C5 3.2228 . . no O7 C10 3.0804 . 3_555 no O7 C1 2.7674 . . no O7 S1 3.1342 . . no O7 F9 3.0178 . . no O8 N3 3.1572 . . no O8 F8 2.7231 . . no O8 C9 3.2917 . . no O8 C10 3.0829 . . no O8 C1 2.6817 . . no O1 H3 2.4900 . 3_545 no O2 H7 2.7700 . 1_655 no O2 H8 2.8300 . 3_555 no O3 H1 2.7100 . 3_555 no O4 H3 2.4400 . 3_545 no O5 H6 2.7400 . 1_655 no O6 H8 2.4700 . 3_555 no O7 H1 2.2500 . 3_555 no N1 F5 3.0536 . . no N1 F3 3.0756 . . no N1 F2 2.7866 . . no N1 F6 2.9310 . . no N1 C10 3.2559 . 3_555 no N2 C6 3.1851 . 3_545 no N2 F7 2.5855 . . no N2 F8 3.1674 . . no N2 F10 2.7155 . . no N2 C1 2.4508 . . no N2 C2 2.7970 . . no N3 O8 3.1572 . . no N4 F6 3.1975 . 4_454 no N4 F2 3.1402 . 1_455 no N4 F4 3.2090 . 2_454 no N4 C11 3.3400 . 4_454 no N4 F12 2.8974 . 4_454 no N1 H1 2.3100 . 3_555 no N2 H3 2.2600 . 3_545 no N4 H9 2.5000 . 4_454 no N4 H4 2.8500 . 4_454 no C3 S1 3.5622 . . no C4 S2 3.6837 . . no C5 O2 3.0774 . 1_455 no C5 O3 3.2176 . . no C5 O6 3.3324 . 1_455 no C5 O7 3.2228 . . no C6 N2 3.1851 . 3_455 no C6 O2 3.2678 . 1_455 no C6 O3 3.0926 . . no C6 O1 3.2082 . 3_455 no C6 O4 3.2583 . 3_455 no C7 F7 3.3218 . 1_455 no C8 F7 3.0645 . 1_455 no C8 F2 3.1890 . 1_455 no C8 F4 3.2879 . 2_454 no C9 O8 3.2917 . . no C9 F7 3.2250 . 1_455 no C9 O5 3.1613 . 1_455 no C10 O1 3.3954 . 1_455 no C10 O8 3.0829 . . no C10 O3 3.3865 . 3_445 no C10 O5 2.9611 . 1_455 no C10 O7 3.0804 . 3_445 no C10 N1 3.2559 . 3_445 no C11 F1 3.0764 . 2_555 no C11 F5 3.2559 . . no C11 N4 3.3400 . 4_555 no C11 F8 3.1701 . 2_555 no C12 O2 3.4076 . 1_455 no C12 F6 3.2499 . 3_445 no C12 O5 3.4084 . 1_455 no C12 F1 3.2607 . 2_555 no C5 H7 3.0200 . . no C10 H6 2.9400 . . no H1 H8 2.3500 . . no H1 S2 3.1200 . 3_445 no H1 O3 2.7100 . 3_445 no H1 N1 2.3100 . 3_445 no H1 S4 3.1200 . 3_445 no H1 O7 2.2500 . 3_445 no H2 F4 2.6200 . 2_454 no H2 F11 2.5900 . 2_454 no H3 O1 2.4900 . 3_455 no H3 O4 2.4400 . 3_455 no H3 N2 2.2600 . 3_455 no H4 H9 2.3400 . . no H4 N4 2.8500 . 4_555 no H5 F1 2.5900 . 2_555 no H5 F8 2.8300 . 2_555 no H6 C10 2.9400 . . no H6 O5 2.7400 . 1_455 no H7 O2 2.7700 . 1_455 no H7 C5 3.0200 . . no H7 F9 2.8500 . 4_455 no H8 H1 2.3500 . . no H8 F1 2.7900 . 2_555 no H8 O2 2.8300 . 3_445 no H8 O6 2.4700 . 3_445 no H9 F5 2.5700 . . no H9 H4 2.3400 . . no H9 F1 2.7900 . 2_555 no H9 F8 2.7000 . 2_555 no H9 N4 2.5000 . 4_555 no #===END data_22 _database_code_depnum_ccdc_archive 'CCDC 690237' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-Methyl-3-cyanopyridinium bis{(trifluoromethyl)sulfonyl}amide ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H7 F6 N3 O4 S2' _chemical_formula_weight 399.30 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' 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 7.4620(6) _cell_length_b 26.715(2) _cell_length_c 7.8762(7) _cell_angle_alpha 90.00 _cell_angle_beta 113.876(2) _cell_angle_gamma 90.00 _cell_volume 1435.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.847 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.465 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8358 _exptl_absorpt_correction_T_max 0.9816 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.77490 _diffrn_radiation_type 'synchrotron radiation' _diffrn_radiation_source 'advanced light source station 11.3.1' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker Platinum 200 CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15064 _diffrn_reflns_av_R_equivalents 0.0332 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -38 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 33.63 _reflns_number_total 4287 _reflns_number_gt 3934 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT v7.34a' _computing_data_reduction 'Bruker SAINT v7.34a' _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 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^)+(0.0879P)^2^+0.4492P] 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 geom _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4287 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0530 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1504 _refine_ls_wR_factor_gt 0.1349 _refine_ls_goodness_of_fit_ref 1.154 _refine_ls_restrained_S_all 1.154 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 33.63 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.663 _refine_diff_density_min -0.560 _refine_diff_density_rms 0.188 loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags N2 N Uani 0.76310 -0.00497 0.51350 1.000 0.0453 . . N3 N Uani 0.78200 0.09740 0.02480 1.000 0.0330 . . C3 C Uani 0.76120 0.01146 0.37870 1.000 0.0347 . . C4 C Uani 0.76150 0.02970 0.20730 1.000 0.0298 . . C5 C Uani 0.77730 0.08041 0.18400 1.000 0.0320 . . C6 C Uani 0.76970 0.06592 -0.11220 1.000 0.0387 . . C7 C Uani 0.75160 0.01522 -0.09510 1.000 0.0409 . . C8 C Uani 0.74820 -0.00370 0.06750 1.000 0.0350 . . C9 C Uani 0.80020 0.15177 0.00040 1.000 0.0468 . . S1 S Uani 0.18755 0.12980 0.62679 1.000 0.0283 . . S2 S Uani 0.34289 0.12393 0.35462 1.000 0.0318 . . F1 F Uani 0.27040 0.21644 0.23830 1.000 0.0691 . . F2 F Uani 0.52210 0.20729 0.49330 1.000 0.0744 . . F3 F Uani 0.53490 0.18568 0.23710 1.000 0.0705 . . F4 F Uani 0.12740 0.19879 0.82920 1.000 0.0677 . . F5 F Uani 0.29280 0.22362 0.68050 1.000 0.0951 . . F6 F Uani -0.01430 0.21225 0.53830 1.000 0.0951 . . O1 O Uani 0.37200 0.11650 0.76890 1.000 0.0440 . . O2 O Uani 0.01750 0.10496 0.62530 1.000 0.0461 . . O3 O Uani 0.51640 0.10041 0.47940 1.000 0.0548 . . O4 O Uani 0.25550 0.10564 0.16860 1.000 0.0497 . . N1 N Uani 0.17490 0.13243 0.42360 1.000 0.0302 . . C1 C Uani 0.41910 0.18747 0.32910 1.000 0.0462 . . C2 C Uani 0.14610 0.19501 0.67060 1.000 0.0473 . . H1 H Uiso 0.73700 -0.03870 0.08300 1.000 0.0420 . . H2 H Uiso 0.74140 -0.00670 -0.19370 1.000 0.0490 . . H3 H Uiso 0.77370 0.07890 -0.22290 1.000 0.0464 . . H4 H Uiso 0.80190 0.15800 -0.12150 1.000 0.0703 . . H5 H Uiso 0.92220 0.16410 0.09780 1.000 0.0703 . . H6 H Uiso 0.68850 0.16920 0.00870 1.000 0.0703 . . H7 H Uiso 0.78470 0.10320 0.27940 1.000 0.0383 . . 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 N2 0.0641 0.0460 0.0338 0.0018 0.0280 -0.0010 N3 0.0247 0.0438 0.0273 0.0088 0.0071 -0.0006 C3 0.0408 0.0372 0.0299 -0.0004 0.0182 -0.0012 C4 0.0272 0.0399 0.0224 0.0021 0.0101 -0.0002 C5 0.0286 0.0408 0.0244 0.0007 0.0086 -0.0032 C6 0.0340 0.0568 0.0258 0.0095 0.0127 0.0061 C7 0.0462 0.0542 0.0257 0.0009 0.0182 0.0069 C8 0.0387 0.0403 0.0283 0.0008 0.0159 0.0037 C9 0.0399 0.0456 0.0474 0.0157 0.0098 -0.0053 S1 0.0269 0.0313 0.0263 0.0009 0.0104 -0.0008 S2 0.0337 0.0323 0.0330 0.0036 0.0171 0.0032 F1 0.0889 0.0422 0.0877 0.0243 0.0476 0.0131 F2 0.0817 0.0783 0.0711 -0.0277 0.0392 -0.0457 F3 0.0888 0.0656 0.0891 0.0037 0.0692 -0.0138 F4 0.1047 0.0592 0.0602 -0.0107 0.0549 0.0064 F5 0.1437 0.0459 0.1440 -0.0364 0.1080 -0.0369 F6 0.1240 0.0785 0.0750 0.0126 0.0322 0.0648 O1 0.0371 0.0598 0.0291 0.0036 0.0071 0.0096 O2 0.0414 0.0593 0.0438 -0.0038 0.0238 -0.0153 O3 0.0410 0.0704 0.0584 0.0249 0.0258 0.0231 O4 0.0634 0.0510 0.0430 -0.0129 0.0300 -0.0061 N1 0.0277 0.0365 0.0258 0.0012 0.0102 0.0012 C1 0.0542 0.0426 0.0526 -0.0008 0.0328 -0.0101 C2 0.0666 0.0381 0.0476 -0.0013 0.0338 0.0056 _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 N1 1.5661 . . yes S1 O1 1.4235 . . yes S1 O2 1.4278 . . yes S1 C2 1.8265 . . yes S2 N1 1.5714 . . yes S2 O3 1.4167 . . yes S2 O4 1.4273 . . yes S2 C1 1.8269 . . yes F1 C1 1.3036 . . yes F2 C1 1.3187 . . yes F3 C1 1.3345 . . yes F4 C2 1.3157 . . yes F5 C2 1.3113 . . yes F6 C2 1.3118 . . yes N2 C3 1.1436 . . yes N3 C9 1.4786 . . yes N3 C5 1.3473 . . yes N3 C6 1.3416 . . yes C3 C4 1.4361 . . no C4 C8 1.3892 . . no C4 C5 1.3785 . . no C6 C7 1.3732 . . no C7 C8 1.3866 . . no C5 H7 0.9500 . . no C6 H3 0.9500 . . no C7 H2 0.9500 . . no C8 H1 0.9500 . . no C9 H6 0.9800 . . no C9 H4 0.9800 . . no C9 H5 0.9800 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 S1 C2 101.86 . . . yes O1 S1 N1 116.99 . . . yes O1 S1 C2 105.86 . . . yes O1 S1 O2 117.63 . . . yes O2 S1 C2 103.12 . . . yes O2 S1 N1 109.07 . . . yes O3 S2 C1 104.52 . . . yes O3 S2 N1 117.21 . . . yes O3 S2 O4 118.02 . . . yes N1 S2 C1 103.37 . . . yes O4 S2 N1 107.90 . . . yes O4 S2 C1 103.79 . . . yes C5 N3 C6 121.22 . . . yes C5 N3 C9 119.36 . . . yes C6 N3 C9 119.42 . . . yes S1 N1 S2 128.33 . . . yes N2 C3 C4 177.17 . . . yes C5 C4 C8 120.54 . . . no C3 C4 C8 120.02 . . . no C3 C4 C5 119.43 . . . no N3 C5 C4 119.39 . . . yes N3 C6 C7 121.12 . . . yes C6 C7 C8 119.30 . . . no C4 C8 C7 118.41 . . . no N3 C5 H7 120.00 . . . no C4 C5 H7 120.00 . . . no C7 C6 H3 119.00 . . . no N3 C6 H3 119.00 . . . no C8 C7 H2 120.00 . . . no C6 C7 H2 120.00 . . . no C7 C8 H1 121.00 . . . no C4 C8 H1 121.00 . . . no H5 C9 H6 110.00 . . . no H4 C9 H6 109.00 . . . no N3 C9 H4 109.00 . . . no N3 C9 H5 109.00 . . . no N3 C9 H6 109.00 . . . no H4 C9 H5 109.00 . . . no S2 C1 F1 112.23 . . . yes S2 C1 F2 110.43 . . . yes S2 C1 F3 108.98 . . . yes F1 C1 F2 109.17 . . . yes F1 C1 F3 108.53 . . . yes F2 C1 F3 107.36 . . . yes S1 C2 F4 110.10 . . . yes S1 C2 F5 111.47 . . . yes S1 C2 F6 110.77 . . . yes F4 C2 F5 107.79 . . . yes F4 C2 F6 108.30 . . . yes F5 C2 F6 108.30 . . . yes 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 O1 S1 C2 F6 175.18 . . . . no O2 S1 C2 F6 -60.68 . . . . no N1 S1 C2 F6 52.38 . . . . no O1 S1 N1 S2 -2.22 . . . . no O2 S1 N1 S2 -138.82 . . . . no C2 S1 N1 S2 112.64 . . . . no O1 S1 C2 F5 54.52 . . . . no O2 S1 C2 F5 178.66 . . . . no N1 S1 C2 F5 -68.28 . . . . no O2 S1 C2 F4 59.08 . . . . no N1 S1 C2 F4 172.14 . . . . no O1 S1 C2 F4 -65.06 . . . . no N1 S2 C1 F3 -168.08 . . . . no N1 S2 C1 F1 -47.84 . . . . no O3 S2 C1 F3 68.77 . . . . no O4 S2 C1 F3 -55.52 . . . . no O3 S2 C1 F1 -170.99 . . . . no O4 S2 C1 F1 64.72 . . . . no O3 S2 C1 F2 -48.93 . . . . no O4 S2 C1 F2 -173.22 . . . . no N1 S2 C1 F2 74.22 . . . . no O3 S2 N1 S1 15.42 . . . . no O4 S2 N1 S1 151.58 . . . . no C1 S2 N1 S1 -98.90 . . . . no C9 N3 C5 C4 -179.62 . . . . no C5 N3 C6 C7 0.09 . . . . no C6 N3 C5 C4 0.65 . . . . no C9 N3 C6 C7 -179.65 . . . . no C3 C4 C5 N3 178.52 . . . . no C5 C4 C8 C7 0.12 . . . . no C3 C4 C8 C7 -179.14 . . . . no C8 C4 C5 N3 -0.75 . . . . no N3 C6 C7 C8 -0.72 . . . . no C6 C7 C8 C4 0.60 . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag S2 N2 3.5312 . 3_656 no S2 H5 3.1600 . 1_455 no F1 O4 3.0043 . . no F1 N1 2.9184 . . no F1 F2 2.9007 . 4_454 no F1 F4 2.9933 . 1_554 no F2 F5 2.7082 . . no F2 F4 3.0668 . 4_554 no F2 F1 2.9007 . 4_555 no F2 O3 2.8571 . . no F2 N1 3.1404 . . no F3 O3 3.0106 . . no F3 C9 3.3471 . . no F3 O4 2.8809 . . no F3 F6 3.0914 . 4_554 no F4 F2 3.0668 . 4_455 no F4 O2 2.9101 . . no F4 F1 2.9933 . 1_556 no F4 O1 3.0152 . . no F5 N1 3.0597 . . no F5 F2 2.7082 . . no F5 F6 3.1089 . 4_555 no F5 O1 2.9479 . . no F6 F3 3.0914 . 4_455 no F6 N1 2.8964 . . no F6 F5 3.1089 . 4_454 no F6 O2 2.9342 . . no F1 H5 2.7600 . 1_455 no F3 H6 2.5300 . . no F3 H7 2.8200 . . no F4 H4 2.8300 . 1_456 no O1 F4 3.0152 . . no O1 C6 3.0430 . 1_556 no O1 C9 3.1154 . 1_556 no O1 F5 2.9479 . . no O1 O3 2.9213 . . no O1 N3 2.9480 . 1_556 no O2 C5 3.2681 . 1_455 no O2 F6 2.9342 . . no O2 F4 2.9101 . . no O2 C3 3.2653 . 1_455 no O3 C6 3.1379 . 1_556 no O3 C3 3.2841 . . no O3 F2 2.8571 . . no O3 O1 2.9213 . . no O3 F3 3.0106 . . no O4 C9 3.3426 . 1_455 no O4 N3 3.2520 . 1_455 no O4 C8 3.2915 . 3_655 no O4 F3 2.8809 . . no O4 F1 3.0043 . . no O4 C7 3.2769 . 3_655 no O1 H1 2.6700 . 3_656 no O1 H6 2.7400 . 1_556 no O2 H1 2.8900 . 3_656 no O2 H3 2.6400 . 1_456 no O2 H7 2.5700 . 1_455 no O3 H3 2.4200 . 1_556 no O4 H2 2.6500 . 3_655 no O4 H5 2.8000 . 1_455 no O4 H1 2.6900 . 3_655 no N1 F1 2.9184 . . no N1 F2 3.1404 . . no N1 C5 3.1245 . 1_455 no N1 C9 3.4133 . 1_455 no N1 F5 3.0597 . . no N1 F6 2.8964 . . no N2 S2 3.5312 . 3_656 no N2 C7 3.1648 . 1_556 no N2 C3 3.3032 . 3_756 no N2 C4 3.3973 . 3_756 no N3 O1 2.9480 . 1_554 no N3 O4 3.2520 . 1_655 no N1 H7 2.7700 . 1_455 no N1 H5 2.6300 . 1_455 no N2 H2 2.3800 . 1_556 no C3 O3 3.2841 . . no C3 O2 3.2653 . 1_655 no C3 N2 3.3032 . 3_756 no C3 C3 3.3488 . 3_756 no C4 N2 3.3973 . 3_756 no C5 O2 3.2681 . 1_655 no C5 N1 3.1245 . 1_655 no C6 O1 3.0430 . 1_554 no C6 O3 3.1379 . 1_554 no C7 C7 3.4861 . 3_755 no C7 O4 3.2769 . 3_655 no C7 N2 3.1648 . 1_554 no C8 O4 3.2915 . 3_655 no C8 C8 3.4208 . 3_655 no C9 F3 3.3471 . . no C9 N1 3.4133 . 1_655 no C9 O1 3.1154 . 1_554 no C9 O4 3.3426 . 1_655 no H1 O4 2.6900 . 3_655 no H1 O1 2.6700 . 3_656 no H1 O2 2.8900 . 3_656 no H2 N2 2.3800 . 1_554 no H2 O4 2.6500 . 3_655 no H3 O2 2.6400 . 1_654 no H3 O3 2.4200 . 1_554 no H3 H4 2.2400 . . no H4 H3 2.2400 . . no H4 F4 2.8300 . 1_654 no H5 F1 2.7600 . 1_655 no H5 S2 3.1600 . 1_655 no H5 O4 2.8000 . 1_655 no H5 N1 2.6300 . 1_655 no H6 F3 2.5300 . . no H6 O1 2.7400 . 1_554 no H7 N1 2.7700 . 1_655 no H7 F3 2.8200 . . no H7 O2 2.5700 . 1_655 no #===END data_24 _database_code_depnum_ccdc_archive 'CCDC 690238' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-Ethyl-3-cyanopyridinium bis{(trifluoromethyl)sulfonyl}amide ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H9 F6 N3 O4 S2' _chemical_formula_weight 413.32 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' 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 8.226(8) _cell_length_b 15.886(15) _cell_length_c 12.553(12) _cell_angle_alpha 90.00 _cell_angle_beta 91.871(18) _cell_angle_gamma 90.00 _cell_volume 1639(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2605 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 22.77 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.675 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.410 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details SADABS _exptl_special_details ; Ratio of minimum to maximum transmission: 0.812289 ; _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15495 _diffrn_reflns_av_R_equivalents 0.0635 _diffrn_reflns_av_sigmaI/netI 0.0956 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 24.98 _reflns_number_total 2873 _reflns_number_gt 1738 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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 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^)+(0.1327P)^2^+4.5618P] 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 calc _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2873 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1343 _refine_ls_R_factor_gt 0.0909 _refine_ls_wR_factor_ref 0.2954 _refine_ls_wR_factor_gt 0.2428 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.974 _refine_diff_density_min -0.431 _refine_diff_density_rms 0.098 loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags N2 N Uani 0.19760 0.34820 0.80120 1.000 0.1123 . . N3 N Uani 0.26310 0.11620 0.57300 1.000 0.0542 . . C3 C Uani 0.21150 0.28200 0.76890 1.000 0.0725 . . C4 C Uani 0.23240 0.20000 0.72560 1.000 0.0528 . . C5 C Uani 0.24240 0.19160 0.61570 1.000 0.0550 . . C6 C Uani 0.27140 0.04750 0.63240 1.000 0.0567 . . C7 C Uani 0.26030 0.05250 0.73990 1.000 0.0576 . . C8 C Uani 0.24090 0.12890 0.78830 1.000 0.0584 . . C9 C Uani 0.27730 0.11080 0.45360 1.000 0.0744 . . C10 C Uani 0.11360 0.10880 0.40430 1.000 0.0970 . . S1 S Uani 0.24010 0.36396 0.14673 1.000 0.0542 . . S2 S Uani 0.23060 0.36556 0.36848 1.000 0.0671 . . F1 F Uani 0.28630 0.48440 0.50240 1.000 0.1748 . . F2 F Uani 0.11590 0.51640 0.38420 1.000 0.1839 . . F3 F Uani 0.36350 0.51140 0.34930 1.000 0.1516 . . F4 F Uani 0.09520 0.22120 0.11600 1.000 0.1599 . . F5 F Uani 0.32370 0.20950 0.18590 1.000 0.1285 . . F6 F Uani 0.29960 0.23800 0.02530 1.000 0.1495 . . O1 O Uani 0.13170 0.39920 0.06920 1.000 0.0919 . . O2 O Uani 0.40190 0.38890 0.14730 1.000 0.0902 . . O3 O Uani 0.10820 0.33540 0.43560 1.000 0.1289 . . O4 O Uani 0.38390 0.33090 0.38020 1.000 0.1225 . . N1 N Uani 0.14680 0.36840 0.25520 1.000 0.0791 . . C1 C Uani 0.24770 0.47510 0.40260 1.000 0.0959 . . C2 C Uani 0.23770 0.25330 0.11730 1.000 0.0773 . . H1 H Uiso 0.23360 0.13270 0.86190 1.000 0.0701 . . H2 H Uiso 0.26580 0.00370 0.78090 1.000 0.0691 . . H3 H Uiso 0.28500 -0.00460 0.60030 1.000 0.0680 . . H4 H Uiso 0.12110 0.10380 0.32840 1.000 0.1455 . . H5 H Uiso 0.05510 0.06150 0.43120 1.000 0.1455 . . H6 H Uiso 0.05720 0.15980 0.42090 1.000 0.1455 . . H7 H Uiso 0.33640 0.06040 0.43510 1.000 0.0893 . . H8 H Uiso 0.33640 0.15920 0.42800 1.000 0.0893 . . H9 H Uiso 0.23460 0.23890 0.57210 1.000 0.0660 . . 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 N2 0.1990 0.0530 0.0840 -0.0160 -0.0110 0.0000 N3 0.0620 0.0480 0.0530 0.0000 0.0060 0.0030 C3 0.0980 0.0550 0.0640 -0.0060 -0.0040 -0.0040 C4 0.0590 0.0450 0.0540 -0.0040 -0.0050 -0.0090 C5 0.0670 0.0450 0.0530 0.0000 0.0020 -0.0060 C6 0.0620 0.0410 0.0670 0.0010 0.0020 0.0030 C7 0.0740 0.0410 0.0580 0.0080 0.0050 0.0020 C8 0.0670 0.0530 0.0550 0.0010 -0.0020 0.0020 C9 0.1050 0.0620 0.0570 0.0030 0.0140 0.0080 C10 0.1190 0.1060 0.0660 -0.0130 0.0020 -0.0150 S1 0.0556 0.0527 0.0544 0.0035 0.0036 0.0003 S2 0.0900 0.0586 0.0532 0.0101 0.0102 0.0028 F1 0.2830 0.1530 0.0880 -0.0480 0.0010 -0.0460 F2 0.2080 0.0870 0.2540 -0.0420 -0.0330 0.0480 F3 0.2230 0.1030 0.1310 -0.0110 0.0390 -0.0720 F4 0.1050 0.0760 0.2980 -0.0490 -0.0020 -0.0190 F5 0.1760 0.0690 0.1380 0.0000 -0.0330 0.0350 F6 0.2420 0.1110 0.0980 -0.0390 0.0460 0.0180 O1 0.0840 0.0880 0.1020 0.0100 -0.0220 0.0110 O2 0.0600 0.0910 0.1200 0.0040 0.0100 -0.0160 O3 0.1440 0.1110 0.1350 0.0170 0.0560 -0.0300 O4 0.1130 0.1360 0.1170 0.0100 -0.0210 0.0380 N1 0.0730 0.0870 0.0780 -0.0050 0.0140 0.0040 C1 0.1390 0.0900 0.0590 -0.0060 0.0080 -0.0030 C2 0.0860 0.0740 0.0720 -0.0070 0.0050 0.0010 _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C2 1.7963 . . yes S1 O1 1.4139 . . yes S1 O2 1.3885 . . yes S1 N1 1.5863 . . yes S2 O3 1.4173 . . yes S2 O4 1.3795 . . yes S2 N1 1.5605 . . yes S2 C1 1.7965 . . yes F1 C1 1.2908 . . yes F2 C1 1.2818 . . yes F3 C1 1.3150 . . yes F4 C2 1.2779 . . yes F5 C2 1.2986 . . yes F6 C2 1.3002 . . yes N2 C3 1.1342 . . yes N3 C9 1.5096 . . yes N3 C6 1.3223 . . yes N3 C5 1.3255 . . yes C3 C4 1.4241 . . no C4 C8 1.3771 . . no C4 C5 1.3911 . . no C6 C7 1.3578 . . no C7 C8 1.3689 . . no C9 C10 1.4639 . . no C5 H9 0.9300 . . no C6 H3 0.9300 . . no C7 H2 0.9300 . . no C8 H1 0.9300 . . no C9 H7 0.9700 . . no C9 H8 0.9700 . . no C10 H6 0.9600 . . no C10 H4 0.9600 . . no C10 H5 0.9600 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 O2 118.26 . . . yes O1 S1 N1 105.15 . . . yes O1 S1 C2 104.09 . . . yes O2 S1 N1 118.26 . . . yes O2 S1 C2 106.52 . . . yes N1 S1 C2 102.57 . . . yes O3 S2 O4 117.80 . . . yes O3 S2 N1 104.49 . . . yes O3 S2 C1 103.73 . . . yes O4 S2 N1 118.93 . . . yes O4 S2 C1 107.28 . . . yes N1 S2 C1 102.60 . . . yes C6 N3 C9 120.58 . . . yes C5 N3 C6 121.52 . . . yes C5 N3 C9 117.90 . . . yes S1 N1 S2 124.69 . . . yes N2 C3 C4 178.04 . . . yes C3 C4 C8 122.45 . . . no C5 C4 C8 118.98 . . . no C3 C4 C5 118.56 . . . no N3 C5 C4 120.02 . . . yes N3 C6 C7 120.55 . . . yes C6 C7 C8 120.37 . . . no C4 C8 C7 118.55 . . . no N3 C9 C10 108.73 . . . yes N3 C5 H9 120.00 . . . no C4 C5 H9 120.00 . . . no C7 C6 H3 120.00 . . . no N3 C6 H3 120.00 . . . no C8 C7 H2 120.00 . . . no C6 C7 H2 120.00 . . . no C4 C8 H1 121.00 . . . no C7 C8 H1 121.00 . . . no N3 C9 H8 110.00 . . . no C10 C9 H7 110.00 . . . no N3 C9 H7 110.00 . . . no H7 C9 H8 108.00 . . . no C10 C9 H8 110.00 . . . no H5 C10 H6 109.00 . . . no H4 C10 H6 109.00 . . . no C9 C10 H4 109.00 . . . no C9 C10 H5 109.00 . . . no C9 C10 H6 110.00 . . . no H4 C10 H5 109.00 . . . no S2 C1 F1 110.92 . . . yes S2 C1 F2 113.18 . . . yes S2 C1 F3 110.85 . . . yes F1 C1 F2 107.23 . . . yes F1 C1 F3 106.52 . . . yes F2 C1 F3 107.84 . . . yes S1 C2 F4 113.39 . . . yes S1 C2 F5 112.70 . . . yes S1 C2 F6 111.32 . . . yes F4 C2 F5 105.92 . . . yes F4 C2 F6 107.44 . . . yes F5 C2 F6 105.56 . . . yes 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 O2 S1 C2 F5 58.54 . . . . no N1 S1 C2 F5 -66.36 . . . . no O1 S1 C2 F6 65.86 . . . . no O2 S1 C2 F6 -59.84 . . . . no N1 S1 C2 F6 175.26 . . . . no O1 S1 N1 S2 -158.78 . . . . no O2 S1 N1 S2 -24.16 . . . . no C2 S1 N1 S2 92.63 . . . . no O1 S1 C2 F5 -175.75 . . . . no N1 S1 C2 F4 53.96 . . . . no O1 S1 C2 F4 -55.43 . . . . no O2 S1 C2 F4 178.86 . . . . no O3 S2 C1 F3 177.21 . . . . no O4 S2 C1 F3 51.85 . . . . no N1 S2 C1 F3 -74.21 . . . . no N1 S2 C1 F1 167.67 . . . . no O4 S2 N1 S1 -21.87 . . . . no C1 S2 N1 S1 96.25 . . . . no O3 S2 C1 F1 59.10 . . . . no O4 S2 C1 F1 -66.27 . . . . no O3 S2 C1 F2 -61.48 . . . . no O4 S2 C1 F2 173.16 . . . . no N1 S2 C1 F2 47.10 . . . . no O3 S2 N1 S1 -155.76 . . . . no C9 N3 C5 C4 -178.53 . . . . no C5 N3 C9 C10 -83.95 . . . . no C6 N3 C9 C10 96.13 . . . . no C5 N3 C6 C7 -0.60 . . . . no C9 N3 C6 C7 179.32 . . . . no C6 N3 C5 C4 1.39 . . . . no C3 C4 C5 N3 179.48 . . . . no C3 C4 C8 C7 179.67 . . . . no C5 C4 C8 C7 0.54 . . . . no C8 C4 C5 N3 -1.35 . . . . no N3 C6 C7 C8 -0.23 . . . . no C6 C7 C8 C4 0.23 . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag F1 O3 2.8935 . . no F1 O4 3.0041 . . no F2 N1 2.8708 . . no F2 O3 2.9480 . . no F3 N1 3.0977 . . no F3 O4 2.8977 . . no F4 C5 3.2157 . 4_454 no F4 N1 2.9416 . . no F4 O1 2.9056 . . no F5 C3 3.3261 . 4_554 no F5 O4 3.1360 . . no F5 N1 3.0543 . . no F5 O2 2.9650 . . no F6 C3 3.3497 . 1_554 no F6 O1 2.9696 . . no F6 O3 3.0428 . 4_554 no F6 O2 2.9523 . . no F1 H2 2.7800 . 2_556 no F3 H4 2.6800 . 2_555 no F6 H1 2.6900 . 1_554 no O1 F6 2.9696 . . no O1 N3 3.0439 . 4_454 no O1 F4 2.9056 . . no O1 C6 3.2069 . 4_454 no O1 C9 3.2177 . 4_454 no O2 C4 3.1902 . 4_554 no O2 N3 3.1441 . 4_554 no O2 C8 3.2660 . 4_554 no O2 F5 2.9650 . . no O2 F6 2.9523 . . no O2 O4 3.0735 . . no O2 C7 3.2689 . 4_554 no O2 C5 3.1162 . 4_554 no O2 C6 3.2143 . 4_554 no O3 F2 2.9480 . . no O3 F1 2.8935 . . no O3 C5 3.3742 . . no O3 F6 3.0428 . 4_455 no O4 F5 3.1360 . . no O4 F3 2.8977 . . no O4 O2 3.0735 . . no O4 F1 3.0041 . . no O4 C8 3.2533 . 4_554 no O1 H7 2.5700 . 2_555 no O1 H3 2.7300 . 2_555 no O3 H9 2.5000 . . no O3 H6 2.8300 . . no O4 H8 2.8200 . . no N1 C7 3.4182 . 4_454 no N1 F3 3.0977 . . no N1 C8 3.3784 . 4_454 no N1 F2 2.8708 . . no N1 F4 2.9416 . . no N1 F5 3.0543 . . no N2 C6 3.2818 . 2_556 no N2 C7 3.3062 . 2_556 no N3 O2 3.1441 . 4_455 no N3 O1 3.0439 . 4_555 no N2 H3 2.6500 . 2_556 no N2 H2 2.7000 . 2_556 no C3 F6 3.3497 . 1_556 no C3 F5 3.3261 . 4_455 no C4 O2 3.1902 . 4_455 no C5 O3 3.3742 . . no C5 F4 3.2157 . 4_555 no C5 O2 3.1162 . 4_455 no C6 O2 3.2143 . 4_455 no C6 O1 3.2069 . 4_555 no C6 N2 3.2818 . 2_546 no C7 O2 3.2689 . 4_455 no C7 N2 3.3062 . 2_546 no C7 N1 3.4182 . 4_555 no C8 O4 3.2533 . 4_455 no C8 O2 3.2660 . 4_455 no C8 N1 3.3784 . 4_555 no C9 O1 3.2177 . 4_555 no C5 H6 2.8800 . . no C6 H5 3.0500 . . no C10 H9 3.0900 . . no H1 F6 2.6900 . 1_556 no H2 F1 2.7800 . 2_546 no H2 N2 2.7000 . 2_546 no H3 N2 2.6500 . 2_546 no H3 H7 2.3700 . . no H3 O1 2.7300 . 2_545 no H4 F3 2.6800 . 2_545 no H5 C6 3.0500 . . no H6 C5 2.8800 . . no H6 O3 2.8300 . . no H7 O1 2.5700 . 2_545 no H7 H3 2.3700 . . no H8 O4 2.8200 . . no H8 H9 2.3800 . . no H9 C10 3.0900 . . no H9 H8 2.3800 . . no H9 O3 2.5000 . . no #===END data_32 _database_code_depnum_ccdc_archive 'CCDC 690239' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-Ethyl-2-cyanopyridinium bis{(trifluoromethyl)sulfonyl}amide ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H9 F6 N3 O4 S2' _chemical_formula_weight 413.32 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' 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) 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' _cell_length_a 12.290(16) _cell_length_b 13.837(20) _cell_length_c 19.51(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3317(8) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.655 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1664 _exptl_absorpt_coefficient_mu 0.406 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details SADABS _exptl_special_details ; Ratio of minimum to maximum transmission: 0.774606 ; _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 31744 _diffrn_reflns_av_R_equivalents 0.1213 _diffrn_reflns_av_sigmaI/netI 0.1241 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5837 _reflns_number_gt 2862 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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 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^)+(0.1022P)^2^+4.3509P] 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 calc _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.027(3) _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 0.08(19) _refine_ls_number_reflns 5837 _refine_ls_number_parameters 452 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1624 _refine_ls_R_factor_gt 0.0775 _refine_ls_wR_factor_ref 0.2581 _refine_ls_wR_factor_gt 0.1819 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.540 _refine_diff_density_min -0.338 _refine_diff_density_rms 0.109 loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags N3 N Uani -0.03450 0.43310 0.48250 1.000 0.0963 . . N4 N Uani 0.13720 0.24180 0.52010 1.000 0.0663 . . C5 C Uani 0.02370 0.36980 0.47760 1.000 0.0750 . . C6 C Uani 0.09640 0.29050 0.46520 1.000 0.0663 . . C7 C Uani 0.20440 0.16660 0.51050 1.000 0.0807 . . C8 C Uani 0.23280 0.13870 0.44470 1.000 0.0867 . . C9 C Uani 0.19690 0.18750 0.39010 1.000 0.0840 . . C10 C Uani 0.12700 0.26470 0.39870 1.000 0.0760 . . C11 C Uani 0.10550 0.26960 0.59210 1.000 0.0793 . . C12 C Uani 0.00110 0.22470 0.61450 1.000 0.0943 . . N5 N Uani 0.20340 0.28760 0.23590 1.000 0.1197 . . N6 N Uani 0.17030 0.17630 0.08000 1.000 0.0677 . . C13 C Uani 0.22530 0.25020 0.18570 1.000 0.0830 . . C14 C Uani 0.25270 0.20330 0.12140 1.000 0.0630 . . C15 C Uani 0.19300 0.13370 0.01880 1.000 0.0790 . . C16 C Uani 0.29420 0.11560 -0.00010 1.000 0.0860 . . C17 C Uani 0.38000 0.13970 0.04180 1.000 0.0897 . . C18 C Uani 0.35720 0.18520 0.10460 1.000 0.0837 . . C19 C Uani 0.05280 0.19760 0.09750 1.000 0.0923 . . C20 C Uani 0.01200 0.12640 0.14930 1.000 0.0977 . . S1 S Uani 0.75490 0.45313 0.27978 1.000 0.0724 . . S2 S Uani 0.59580 0.39540 0.18657 1.000 0.0957 . . F1 F Uani 0.51280 0.55870 0.21910 1.000 0.2203 . . F2 F Uani 0.42230 0.47930 0.14430 1.000 0.1683 . . F3 F Uani 0.41730 0.44190 0.24890 1.000 0.1700 . . F4 F Uani 0.86190 0.29360 0.28880 1.000 0.1873 . . F5 F Uani 0.87420 0.35950 0.19200 1.000 0.1603 . . F6 F Uani 0.96120 0.41360 0.27780 1.000 0.1270 . . O1 O Uani 0.77350 0.54120 0.24220 1.000 0.0943 . . O2 O Uani 0.75980 0.45860 0.35440 1.000 0.1060 . . O3 O Uani 0.54830 0.30590 0.17480 1.000 0.1803 . . O4 O Uani 0.65500 0.43860 0.13300 1.000 0.1610 . . N1 N Uani 0.65410 0.39210 0.25890 1.000 0.0800 . . C1 C Uani 0.48440 0.47300 0.19910 1.000 0.1093 . . C2 C Uani 0.86460 0.37600 0.25870 1.000 0.0953 . . S3 S Uani 0.23130 0.43082 -0.00976 1.000 0.0754 . . S4 S Uani 0.11680 0.58142 0.05086 1.000 0.0712 . . F7 F Uani 0.20920 0.58680 0.17300 1.000 0.1213 . . F8 F Uani 0.03630 0.58950 0.17510 1.000 0.1203 . . F9 F Uani 0.11890 0.45960 0.15300 1.000 0.1453 . . F10 F Uani 0.27460 0.51240 -0.12780 1.000 0.1400 . . F11 F Uani 0.21860 0.37060 -0.13600 1.000 0.1333 . . F12 F Uani 0.10520 0.47910 -0.11200 1.000 0.1390 . . O5 O Uani 0.34150 0.39810 -0.00650 1.000 0.1047 . . O6 O Uani 0.14480 0.36620 0.01020 1.000 0.0993 . . O7 O Uani 0.12980 0.68370 0.05040 1.000 0.0867 . . O8 O Uani 0.01610 0.54460 0.02610 1.000 0.0930 . . N2 N Uani 0.22400 0.53470 0.02220 1.000 0.0647 . . C3 C Uani 0.12110 0.55130 0.14210 1.000 0.0837 . . C4 C Uani 0.20830 0.45220 -0.09980 1.000 0.0957 . . H1 H Uiso 0.10080 0.29870 0.36110 1.000 0.0912 . . H2 H Uiso 0.21900 0.16960 0.34630 1.000 0.1008 . . H3 H Uiso 0.27760 0.08520 0.43840 1.000 0.1040 . . H4 H Uiso 0.23200 0.13320 0.54810 1.000 0.0968 . . H5 H Uiso -0.01530 0.24500 0.66040 1.000 0.1415 . . H6 H Uiso 0.00780 0.15560 0.61320 1.000 0.1415 . . H7 H Uiso -0.05630 0.24470 0.58430 1.000 0.1415 . . H8 H Uiso 0.16290 0.25010 0.62330 1.000 0.0952 . . H9 H Uiso 0.09880 0.33930 0.59470 1.000 0.0952 . . H10 H Uiso 0.41320 0.20240 0.13410 1.000 0.1004 . . H11 H Uiso 0.45130 0.12640 0.02880 1.000 0.1076 . . H12 H Uiso 0.30750 0.08610 -0.04210 1.000 0.1032 . . H13 H Uiso 0.13610 0.11710 -0.01040 1.000 0.0948 . . H14 H Uiso -0.06250 0.14050 0.16010 1.000 0.1465 . . H15 H Uiso 0.05530 0.13070 0.19020 1.000 0.1465 . . H16 H Uiso 0.01720 0.06220 0.13080 1.000 0.1465 . . H17 H Uiso 0.04680 0.26250 0.11590 1.000 0.1108 . . H18 H Uiso 0.00860 0.19380 0.05640 1.000 0.1108 . . 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 N3 0.0870 0.0900 0.1120 0.0050 0.0130 0.0180 N4 0.0660 0.0660 0.0670 -0.0060 -0.0160 -0.0110 C5 0.0670 0.0710 0.0870 0.0090 0.0010 -0.0040 C6 0.0600 0.0630 0.0760 0.0030 -0.0080 0.0010 C7 0.0830 0.0610 0.0980 0.0080 -0.0200 0.0090 C8 0.0770 0.0680 0.1150 -0.0060 0.0010 -0.0110 C9 0.0760 0.0870 0.0890 -0.0120 0.0110 0.0060 C10 0.0790 0.0820 0.0670 0.0010 -0.0040 0.0050 C11 0.0910 0.0780 0.0690 0.0010 -0.0060 0.0020 C12 0.0900 0.1170 0.0760 0.0070 0.0080 -0.0100 N5 0.1740 0.1040 0.0810 -0.0120 0.0050 0.0130 N6 0.0590 0.0780 0.0660 0.0020 0.0000 -0.0080 C13 0.0940 0.0830 0.0720 0.0030 0.0020 -0.0030 C14 0.0720 0.0590 0.0580 -0.0020 0.0020 -0.0010 C15 0.0890 0.0820 0.0660 -0.0070 0.0060 -0.0080 C16 0.1050 0.0790 0.0740 -0.0050 0.0140 0.0000 C17 0.0700 0.0880 0.1110 0.0170 0.0170 0.0020 C18 0.0740 0.0890 0.0880 -0.0020 -0.0110 0.0070 C19 0.0750 0.1010 0.1010 0.0090 0.0000 -0.0030 C20 0.0840 0.0900 0.1190 0.0110 0.0000 0.0040 S1 0.0767 0.0677 0.0728 0.0067 -0.0036 -0.0068 S2 0.0850 0.1120 0.0900 -0.0224 -0.0091 -0.0015 F1 0.2210 0.1170 0.3230 -0.0270 -0.0780 0.0540 F2 0.1300 0.2520 0.1230 0.0270 -0.0330 0.0500 F3 0.1170 0.2730 0.1200 0.0130 0.0160 0.0410 F4 0.1640 0.1010 0.2970 0.0750 0.0290 0.0460 F5 0.1340 0.2110 0.1360 -0.0600 0.0170 0.0430 F6 0.0900 0.1410 0.1500 0.0090 0.0040 0.0110 O1 0.1210 0.0550 0.1070 0.0310 -0.0050 -0.0140 O2 0.1060 0.1580 0.0540 -0.0020 0.0000 -0.0010 O3 0.1410 0.1030 0.2970 -0.0700 -0.1030 -0.0120 O4 0.1080 0.3140 0.0610 -0.0040 0.0210 -0.0390 N1 0.0730 0.0900 0.0770 0.0090 -0.0180 -0.0240 C1 0.0900 0.1500 0.0880 0.0090 -0.0120 0.0360 C2 0.0730 0.1010 0.1120 0.0000 0.0110 0.0010 S3 0.0701 0.0674 0.0888 0.0020 0.0052 0.0061 S4 0.0641 0.0645 0.0850 0.0054 -0.0005 0.0019 F7 0.1130 0.1610 0.0900 0.0060 -0.0170 0.0090 F8 0.1250 0.1320 0.1040 0.0080 0.0360 0.0260 F9 0.2340 0.0770 0.1250 0.0310 0.0610 0.0300 F10 0.1880 0.1400 0.0920 0.0240 0.0240 -0.0430 F11 0.1500 0.1410 0.1090 -0.0410 0.0000 -0.0030 F12 0.1200 0.2000 0.0970 0.0050 -0.0200 0.0340 O5 0.0690 0.1170 0.1280 -0.0060 -0.0010 0.0380 O6 0.0920 0.0690 0.1370 0.0070 0.0250 -0.0220 O7 0.0970 0.0430 0.1200 0.0090 -0.0060 0.0030 O8 0.0570 0.0960 0.1260 -0.0130 -0.0200 -0.0080 N2 0.0610 0.0520 0.0810 -0.0060 0.0070 0.0060 C3 0.0820 0.0810 0.0880 0.0090 0.0220 0.0020 C4 0.1010 0.0950 0.0910 -0.0060 0.0100 0.0130 _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.4407 . . yes S1 O2 1.4590 . . yes S1 N1 1.5537 . . yes S1 C2 1.7681 . . yes S2 O3 1.3885 . . yes S2 O4 1.4068 . . yes S2 N1 1.5833 . . yes S2 C1 1.7572 . . yes S3 O6 1.4428 . . yes S3 N2 1.5697 . . yes S3 C4 1.8037 . . yes S3 O5 1.4295 . . yes S4 O7 1.4246 . . yes S4 O8 1.4229 . . yes S4 C3 1.8290 . . yes S4 N2 1.5705 . . yes F1 C1 1.2965 . . yes F2 C1 1.3165 . . yes F3 C1 1.3451 . . yes F4 C2 1.2832 . . yes F5 C2 1.3265 . . yes F6 C2 1.3488 . . yes F7 C3 1.3331 . . yes F8 C3 1.3342 . . yes F9 C3 1.2871 . . yes F10 C4 1.2871 . . yes F11 C4 1.3380 . . yes F12 C4 1.3419 . . yes N3 C5 1.1350 . . yes N4 C7 1.3418 . . yes N4 C6 1.3612 . . yes N4 C11 1.5077 . . yes N5 C13 1.1400 . . yes N6 C14 1.3482 . . yes N6 C15 1.3606 . . yes N6 C19 1.5129 . . yes C5 C6 1.4357 . . no C6 C10 1.3972 . . no C7 C8 1.3853 . . no C8 C9 1.3363 . . no C9 C10 1.3812 . . no C11 C12 1.4911 . . no C7 H4 0.9300 . . no C8 H3 0.9300 . . no C9 H2 0.9300 . . no C10 H1 0.9300 . . no C11 H8 0.9700 . . no C11 H9 0.9700 . . no C12 H6 0.9600 . . no C12 H7 0.9600 . . no C12 H5 0.9600 . . no C13 C14 1.4521 . . no C14 C18 1.3489 . . no C15 C16 1.3212 . . no C16 C17 1.3753 . . no C17 C18 1.4058 . . no C19 C20 1.4979 . . no C15 H13 0.9300 . . no C16 H12 0.9300 . . no C17 H11 0.9300 . . no C18 H10 0.9300 . . no C19 H17 0.9700 . . no C19 H18 0.9700 . . no C20 H16 0.9600 . . no C20 H15 0.9600 . . no C20 H14 0.9600 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 N1 116.94 . . . yes O1 S1 C2 105.75 . . . yes O2 S1 N1 108.83 . . . yes O2 S1 C2 103.41 . . . yes N1 S1 C2 102.64 . . . yes O1 S1 O2 117.22 . . . yes O3 S2 O4 118.28 . . . yes O3 S2 C1 103.93 . . . yes O4 S2 N1 116.13 . . . yes O3 S2 N1 108.18 . . . yes N1 S2 C1 104.25 . . . yes O4 S2 C1 104.27 . . . yes O5 S3 C4 104.11 . . . yes O6 S3 N2 114.74 . . . yes N2 S3 C4 103.16 . . . yes O5 S3 N2 109.06 . . . yes O6 S3 C4 104.42 . . . yes O5 S3 O6 119.32 . . . yes O7 S4 O8 116.83 . . . yes O8 S4 C3 105.90 . . . yes N2 S4 C3 103.20 . . . yes O7 S4 C3 103.26 . . . yes O8 S4 N2 117.47 . . . yes O7 S4 N2 108.23 . . . yes C7 N4 C11 119.15 . . . yes C6 N4 C7 120.06 . . . yes C6 N4 C11 120.77 . . . yes C14 N6 C19 121.86 . . . yes C15 N6 C19 118.57 . . . yes C14 N6 C15 119.46 . . . yes S1 N1 S2 125.37 . . . yes S3 N2 S4 124.51 . . . yes N3 C5 C6 175.13 . . . yes N4 C6 C5 118.37 . . . yes C5 C6 C10 121.29 . . . no N4 C6 C10 120.33 . . . yes N4 C7 C8 120.04 . . . yes C7 C8 C9 120.98 . . . no C8 C9 C10 119.97 . . . no C6 C10 C9 118.55 . . . no N4 C11 C12 112.90 . . . yes N4 C7 H4 120.00 . . . no C8 C7 H4 120.00 . . . no C9 C8 H3 119.00 . . . no C7 C8 H3 120.00 . . . no C8 C9 H2 120.00 . . . no C10 C9 H2 120.00 . . . no C6 C10 H1 121.00 . . . no C9 C10 H1 121.00 . . . no N4 C11 H9 109.00 . . . no C12 C11 H9 109.00 . . . no C12 C11 H8 109.00 . . . no H8 C11 H9 108.00 . . . no N4 C11 H8 109.00 . . . no H5 C12 H7 110.00 . . . no C11 C12 H7 109.00 . . . no H5 C12 H6 110.00 . . . no H6 C12 H7 110.00 . . . no C11 C12 H5 109.00 . . . no C11 C12 H6 109.00 . . . no N5 C13 C14 179.46 . . . yes N6 C14 C18 121.21 . . . yes N6 C14 C13 117.86 . . . yes C13 C14 C18 120.91 . . . no N6 C15 C16 121.34 . . . yes C15 C16 C17 120.66 . . . no C16 C17 C18 118.29 . . . no C14 C18 C17 119.00 . . . no N6 C19 C20 110.10 . . . yes N6 C15 H13 119.00 . . . no C16 C15 H13 119.00 . . . no C17 C16 H12 120.00 . . . no C15 C16 H12 120.00 . . . no C16 C17 H11 121.00 . . . no C18 C17 H11 121.00 . . . no C14 C18 H10 121.00 . . . no C17 C18 H10 120.00 . . . no H17 C19 H18 108.00 . . . no N6 C19 H18 110.00 . . . no C20 C19 H17 110.00 . . . no C20 C19 H18 110.00 . . . no N6 C19 H17 110.00 . . . no H14 C20 H15 109.00 . . . no H14 C20 H16 110.00 . . . no H15 C20 H16 109.00 . . . no C19 C20 H15 110.00 . . . no C19 C20 H16 109.00 . . . no C19 C20 H14 109.00 . . . no S2 C1 F3 112.49 . . . yes F1 C1 F2 109.87 . . . yes S2 C1 F1 113.03 . . . yes S2 C1 F2 112.28 . . . yes F2 C1 F3 104.62 . . . yes F1 C1 F3 103.91 . . . yes F5 C2 F6 105.02 . . . yes F4 C2 F6 103.84 . . . yes S1 C2 F4 114.23 . . . yes S1 C2 F5 113.58 . . . yes S1 C2 F6 111.96 . . . yes F4 C2 F5 107.35 . . . yes S4 C3 F7 112.31 . . . yes S4 C3 F8 110.90 . . . yes S4 C3 F9 112.64 . . . yes F7 C3 F8 105.67 . . . yes F7 C3 F9 107.80 . . . yes F8 C3 F9 107.13 . . . yes S3 C4 F10 114.86 . . . yes S3 C4 F11 111.15 . . . yes S3 C4 F12 111.48 . . . yes F10 C4 F11 105.22 . . . yes F10 C4 F12 110.05 . . . yes F11 C4 F12 103.29 . . . yes 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 N1 S1 C2 F5 65.75 . . . . no O1 S1 C2 F6 61.42 . . . . no O2 S1 C2 F6 -62.34 . . . . no N1 S1 C2 F6 -175.51 . . . . no O2 S1 C2 F4 55.32 . . . . no N1 S1 C2 F4 -57.85 . . . . no O1 S1 C2 F5 -57.32 . . . . no O2 S1 C2 F5 178.92 . . . . no C2 S1 N1 S2 -92.06 . . . . no O1 S1 N1 S2 23.16 . . . . no O1 S1 C2 F4 179.09 . . . . no O2 S1 N1 S2 158.82 . . . . no O4 S2 C1 F3 179.40 . . . . no N1 S2 C1 F3 -58.36 . . . . no O3 S2 C1 F2 -62.82 . . . . no C1 S2 N1 S1 -98.00 . . . . no O3 S2 C1 F1 172.19 . . . . no O4 S2 C1 F1 -63.29 . . . . no N1 S2 C1 F1 58.95 . . . . no O4 S2 C1 F2 61.70 . . . . no N1 S2 C1 F2 -176.06 . . . . no O3 S2 C1 F3 54.88 . . . . no O3 S2 N1 S1 151.83 . . . . no O4 S2 N1 S1 16.08 . . . . no O5 S3 C4 F12 176.88 . . . . no O6 S3 C4 F12 51.00 . . . . no O5 S3 N2 S4 -158.44 . . . . no O6 S3 N2 S4 -21.57 . . . . no C4 S3 N2 S4 91.34 . . . . no O6 S3 C4 F11 -63.65 . . . . no N2 S3 C4 F11 176.09 . . . . no O6 S3 C4 F10 177.05 . . . . no N2 S3 C4 F10 56.80 . . . . no O5 S3 C4 F10 -57.07 . . . . no N2 S3 C4 F12 -69.25 . . . . no O5 S3 C4 F11 62.23 . . . . no O8 S4 C3 F9 61.71 . . . . no O7 S4 N2 S3 -157.67 . . . . no N2 S4 C3 F9 -62.32 . . . . no C3 S4 N2 S3 93.34 . . . . no O7 S4 C3 F7 -53.03 . . . . no O8 S4 N2 S3 -22.70 . . . . no O8 S4 C3 F7 -176.34 . . . . no N2 S4 C3 F7 59.63 . . . . no O7 S4 C3 F8 64.96 . . . . no O8 S4 C3 F8 -58.36 . . . . no N2 S4 C3 F8 177.62 . . . . no O7 S4 C3 F9 -174.98 . . . . no C7 N4 C6 C5 179.24 . . . . no C11 N4 C6 C5 0.87 . . . . no C7 N4 C6 C10 -2.17 . . . . no C11 N4 C6 C10 179.46 . . . . no C11 N4 C7 C8 178.72 . . . . no C6 N4 C7 C8 0.32 . . . . no C7 N4 C11 C12 -94.12 . . . . no C6 N4 C11 C12 84.27 . . . . no C19 N6 C14 C13 2.76 . . . . no C15 N6 C19 C20 104.85 . . . . no C15 N6 C14 C13 178.85 . . . . no C19 N6 C15 C16 178.23 . . . . no C14 N6 C19 C20 -79.03 . . . . no C15 N6 C14 C18 -2.83 . . . . no C19 N6 C14 C18 -178.91 . . . . no C14 N6 C15 C16 2.02 . . . . no C5 C6 C10 C9 -179.78 . . . . no N4 C6 C10 C9 1.67 . . . . no N4 C7 C8 C9 2.09 . . . . no C7 C8 C9 C10 -2.56 . . . . no C8 C9 C10 C6 0.69 . . . . no C13 C14 C18 C17 -179.97 . . . . no N6 C14 C18 C17 1.77 . . . . no N6 C15 C16 C17 -0.15 . . . . no C15 C16 C17 C18 -0.90 . . . . no C16 C17 C18 C14 0.10 . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag S2 F5 3.4590 . . no F1 N1 2.9892 . . no F1 O4 2.9392 . . no F2 O4 2.9232 . . no F2 F7 3.0637 . . no F2 O3 2.9174 . . no F3 N1 2.9971 . . no F3 F12 2.9388 . 2_565 no F3 O3 2.8679 . . no F4 N1 2.9531 . . no F4 F7 3.0839 . 4_645 no F4 O2 2.9030 . . no F5 O4 3.1274 . . no F5 S2 3.4590 . . no F5 O1 2.9690 . . no F5 N1 3.0372 . . no F6 O1 2.9871 . . no F6 C20 3.2871 . 4_655 no F6 O2 2.9577 . . no F7 N2 3.0346 . . no F7 F4 3.0839 . 4_655 no F7 O7 2.9107 . . no F7 F2 3.0637 . . no F8 O7 2.9898 . . no F8 O8 2.9830 . . no F9 N2 3.0432 . . no F9 O6 3.0878 . . no F9 O8 3.0182 . . no F9 C13 3.2428 . . no F9 N5 3.0596 . . no F10 N2 3.0077 . . no F10 O5 2.9630 . . no F10 C10 3.3536 . 2_564 no F11 O6 2.9937 . . no F11 O5 2.9681 . . no F12 N2 3.0950 . . no F12 F3 2.9389 . 2_564 no F12 O8 3.0464 . . no F12 O6 2.8918 . . no F2 H9 2.7000 . 2_564 no F6 H1 2.8500 . 1_655 no F6 H16 2.7300 . 4_655 no F11 H14 2.7400 . 3_555 no F12 H6 2.8100 . 4_555 no O1 F5 2.9690 . . no O1 C9 3.3007 . 4_655 no O1 C13 3.2165 . 4_655 no O1 F6 2.9871 . . no O1 O4 2.9456 . . no O2 F6 2.9577 . . no O2 C7 3.2270 . 3_556 no O2 F4 2.9030 . . no O3 C18 3.1910 . . no O3 F2 2.9174 . . no O3 F3 2.8679 . . no O4 C15 3.1608 . 3_555 no O4 C16 3.1957 . 3_555 no O4 F2 2.9232 . . no O4 F5 3.1274 . . no O4 O1 2.9456 . . no O4 F1 2.9392 . . no O5 F10 2.9630 . . no O5 C19 3.4132 . 3_555 no O5 F11 2.9681 . . no O6 O8 2.9486 . . no O6 F11 2.9937 . . no O6 F12 2.8918 . . no O6 F9 3.0878 . . no O6 C19 3.1023 . . no O6 C14 3.3983 . . no O6 C17 3.4098 . 3_455 no O6 N6 2.9766 . . no O6 C15 3.2762 . . no O7 C6 3.1632 . 4_555 no O7 C5 3.2390 . 4_555 no O7 C7 3.0084 . 2_564 no O7 F7 2.9107 . . no O7 C11 3.4151 . 2_564 no O7 F8 2.9898 . . no O7 N4 3.1004 . 2_564 no O8 F12 3.0464 . . no O8 C17 3.3255 . 3_455 no O8 O6 2.9486 . . no O8 F9 3.0182 . . no O8 C8 3.3731 . 4_555 no O8 C7 3.2718 . 4_555 no O8 F8 2.9830 . . no O1 H15 2.7800 . 4_655 no O1 H2 2.4800 . 4_655 no O2 H4 2.3100 . 3_556 no O3 H10 2.3300 . . no O4 H3 2.6000 . 4_655 no O4 H13 2.5200 . 3_555 no O4 H12 2.6000 . 3_555 no O5 H18 2.6000 . 3_555 no O6 H11 2.5000 . 3_455 no O6 H17 2.7900 . . no O7 H7 2.9000 . 4_555 no O8 H11 2.7200 . 3_455 no N1 F5 3.0372 . . no N1 F1 2.9892 . . no N1 F3 2.9971 . . no N1 F4 2.9531 . . no N2 F7 3.0346 . . no N2 F9 3.0432 . . no N2 F10 3.0077 . . no N2 F12 3.0950 . . no N3 C8 3.3442 . 3_456 no N3 C15 3.3916 . 4_555 no N4 O7 3.1004 . 2_565 no N5 C10 3.3272 . . no N5 F9 3.0596 . . no N5 C9 3.3131 . . no N6 O6 2.9766 . . no N3 H13 2.8900 . 4_555 no N3 H3 2.7900 . 3_456 no N3 H16 2.8500 . 4_555 no N5 H2 2.7100 . . no N5 H1 2.7500 . . no C5 O7 3.2390 . 4_545 no C5 C12 3.3532 . . no C6 O7 3.1632 . 4_545 no C7 O2 3.2270 . 3_456 no C7 O7 3.0084 . 2_565 no C7 O8 3.2718 . 4_545 no C8 N3 3.3442 . 3_556 no C8 O8 3.3731 . 4_545 no C9 O1 3.3007 . 4_645 no C9 N5 3.3131 . . no C10 N5 3.3272 . . no C10 F10 3.3536 . 2_565 no C11 O7 3.4151 . 2_565 no C12 C5 3.3532 . . no C13 C20 3.2112 . . no C13 F9 3.2428 . . no C13 O1 3.2165 . 4_645 no C14 O6 3.3983 . . no C15 N3 3.3916 . 4_545 no C15 O4 3.1608 . 3_455 no C15 O6 3.2762 . . no C16 O4 3.1957 . 3_455 no C17 O6 3.4098 . 3_555 no C17 O8 3.3255 . 3_555 no C18 O3 3.1910 . . no C19 O6 3.1023 . . no C19 O5 3.4132 . 3_455 no C20 C13 3.2112 . . no C20 F6 3.2871 . 4_645 no C5 H9 2.5000 . . no C5 H7 2.8800 . . no C6 H7 3.0500 . . no C13 H15 2.6700 . . no C13 H17 2.5900 . . no C14 H15 2.9500 . . no H1 N5 2.7500 . . no H1 F6 2.8500 . 1_455 no H2 O1 2.4800 . 4_645 no H2 N5 2.7100 . . no H3 N3 2.7900 . 3_556 no H3 O4 2.6000 . 4_645 no H4 O2 2.3100 . 3_456 no H4 H8 2.3400 . . no H6 F12 2.8100 . 4_545 no H7 C6 3.0500 . . no H7 O7 2.9000 . 4_545 no H7 C5 2.8800 . . no H8 H4 2.3400 . . no H9 F2 2.7000 . 2_565 no H9 C5 2.5000 . . no H10 O3 2.3300 . . no H11 O6 2.5000 . 3_555 no H11 O8 2.7200 . 3_555 no H12 O4 2.6000 . 3_455 no H13 H18 2.3000 . . no H13 N3 2.8900 . 4_545 no H13 O4 2.5200 . 3_455 no H14 F11 2.7400 . 3_455 no H15 C13 2.6700 . . no H15 O1 2.7800 . 4_645 no H15 C14 2.9500 . . no H16 F6 2.7300 . 4_645 no H16 N3 2.8500 . 4_545 no H17 C13 2.5900 . . no H17 O6 2.7900 . . no H18 O5 2.6000 . 3_455 no H18 H13 2.3000 . . no