# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2005 data_global _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Alan R. Katritzky' _publ_contact_author_address ; Department of Chemistry University of Florida Center for Heterocyclic Compounds Gainesville FL 32611 UNITED STATES OF AMERICA ; _publ_contact_author_email KATRITZKY@CHEM.UFL.EDU _publ_section_title ; Strategies Toward the Design of Energetic Ionic Liquids: Nitro- and Nitrile substituted N,N' Dialkylimidazolium Salts ; loop_ _publ_author_name 'Alan R. Katritzky' 'John Holbrey' 'Kostyantyn Kirichenko' 'W. Matthew Reichert' 'R. D. Rogers' ; M.Smiglak ; 'Hongfang Yang' 'Dazhi Zhang' data_3a _database_code_depnum_ccdc_archive 'CCDC 272562' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '1,3-dimethyl-4-nitroimidazolium methylsulfate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H11 N3 O6 S' _chemical_formula_weight 253.24 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 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 8.366(3) _cell_length_b 11.036(4) _cell_length_c 11.379(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.580(6) _cell_angle_gamma 90.00 _cell_volume 1032.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 781 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 23.24 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.86 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.629 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.334 _exptl_absorpt_correction_type sphere _exptl_absorpt_correction_T_min 0.5706 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '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 4636 _diffrn_reflns_av_R_equivalents 0.0497 _diffrn_reflns_av_sigmaI/netI 0.0540 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 23.31 _reflns_number_total 1490 _reflns_number_gt 1210 _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^)+(0.0545P)^2^+0.2935P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1490 _refine_ls_number_parameters 189 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0531 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.0992 _refine_ls_wR_factor_gt 0.0928 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.30772(8) 0.78152(6) 0.16212(6) 0.0193(3) Uani 1 1 d . . . O1 O -0.6021(2) 0.63795(19) -0.15964(17) 0.0297(5) Uani 1 1 d . . . O2 O -0.5355(2) 0.8288(2) -0.15323(17) 0.0300(5) Uani 1 1 d . . . O3 O 0.3916(2) 0.74255(18) 0.29499(16) 0.0265(5) Uani 1 1 d . . . O4 O 0.4304(2) 0.84388(19) 0.11285(17) 0.0316(5) Uani 1 1 d . . . O5 O 0.1763(2) 0.85703(17) 0.18534(16) 0.0259(5) Uani 1 1 d . . . O6 O 0.2535(2) 0.67088(19) 0.09973(18) 0.0341(6) Uani 1 1 d . . . N1 N -0.1691(2) 0.5961(2) 0.07029(18) 0.0176(5) Uani 1 1 d . . . N3 N -0.2568(3) 0.7772(2) 0.01513(18) 0.0178(5) Uani 1 1 d . . . N4 N -0.5125(3) 0.7232(2) -0.12264(19) 0.0211(6) Uani 1 1 d . . . C2 C -0.1372(3) 0.7146(3) 0.0810(2) 0.0194(7) Uani 1 1 d . . . H2A H -0.040(4) 0.749(3) 0.123(2) 0.026(8) Uiso 1 1 d . . . C4 C -0.3675(3) 0.6933(3) -0.0393(2) 0.0172(6) Uani 1 1 d . . . C5 C -0.3140(3) 0.5805(3) -0.0061(2) 0.0182(7) Uani 1 1 d . . . H5A H -0.351(3) 0.500(3) -0.029(2) 0.019(7) Uiso 1 1 d . . . C6 C -0.0683(4) 0.4983(3) 0.1341(3) 0.0231(7) Uani 1 1 d . . . H6A H -0.103(3) 0.475(2) 0.212(2) 0.022(7) Uiso 1 1 d . . . H6B H -0.083(3) 0.430(3) 0.082(3) 0.030(8) Uiso 1 1 d . . . H6C H 0.048(4) 0.526(3) 0.150(3) 0.038(9) Uiso 1 1 d . . . C7 C -0.2564(4) 0.9100(3) 0.0059(3) 0.0275(8) Uani 1 1 d . . . H7A H -0.153(4) 0.940(3) 0.058(3) 0.050(10) Uiso 1 1 d . . . H7B H -0.257(4) 0.931(3) -0.072(3) 0.047(10) Uiso 1 1 d . . . H7C H -0.354(4) 0.939(3) 0.028(3) 0.036(9) Uiso 1 1 d . . . C8 C 0.5304(4) 0.6636(4) 0.3029(3) 0.0388(9) Uani 1 1 d . . . H8A H 0.607(5) 0.700(3) 0.255(3) 0.061(12) Uiso 1 1 d . . . H8C H 0.509(4) 0.584(4) 0.268(3) 0.053(11) Uiso 1 1 d . . . H8B H 0.579(4) 0.655(3) 0.378(3) 0.054(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0193(4) 0.0204(5) 0.0180(4) -0.0020(3) 0.0032(3) -0.0013(3) O1 0.0228(11) 0.0338(14) 0.0295(12) 0.0041(9) -0.0030(9) -0.0066(10) O2 0.0379(13) 0.0254(14) 0.0245(11) 0.0073(9) -0.0002(9) 0.0086(10) O3 0.0262(12) 0.0330(13) 0.0197(11) 0.0021(8) 0.0029(8) 0.0046(9) O4 0.0304(12) 0.0338(14) 0.0337(12) 0.0071(9) 0.0145(9) -0.0017(10) O5 0.0214(11) 0.0277(13) 0.0284(11) -0.0042(9) 0.0040(8) 0.0024(9) O6 0.0344(13) 0.0262(13) 0.0384(13) -0.0144(10) -0.0023(9) -0.0011(10) N1 0.0180(12) 0.0183(14) 0.0160(12) 0.0012(10) 0.0018(9) 0.0007(10) N3 0.0196(13) 0.0179(14) 0.0165(12) -0.0003(10) 0.0047(9) -0.0008(11) N4 0.0201(13) 0.0258(17) 0.0180(12) 0.0007(11) 0.0053(10) -0.0003(12) C2 0.0183(15) 0.0239(19) 0.0163(14) 0.0008(13) 0.0036(11) -0.0005(14) C4 0.0166(14) 0.0225(18) 0.0121(13) 0.0005(11) 0.0021(11) -0.0015(13) C5 0.0186(15) 0.0201(18) 0.0160(14) -0.0026(12) 0.0035(11) -0.0039(13) C6 0.0238(17) 0.0196(18) 0.0236(17) 0.0029(14) -0.0013(13) 0.0042(14) C7 0.0266(19) 0.0184(19) 0.038(2) 0.0034(15) 0.0080(15) 0.0001(15) C8 0.037(2) 0.044(3) 0.033(2) 0.0069(18) -0.0018(17) 0.0155(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O4 1.433(2) . ? S1 O5 1.442(2) . ? S1 O6 1.443(2) . ? S1 O3 1.604(2) . ? O1 N4 1.228(3) . ? O2 N4 1.221(3) . ? O3 C8 1.441(4) . ? N1 C2 1.336(4) . ? N1 C5 1.367(3) . ? N1 C6 1.476(4) . ? N3 C2 1.328(3) . ? N3 C4 1.374(3) . ? N3 C7 1.469(4) . ? N4 C4 1.434(3) . ? C4 C5 1.353(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 S1 O5 114.78(13) . . ? O4 S1 O6 113.39(13) . . ? O5 S1 O6 113.44(12) . . ? O4 S1 O3 106.05(11) . . ? O5 S1 O3 101.46(11) . . ? O6 S1 O3 106.29(12) . . ? C8 O3 S1 115.4(2) . . ? C2 N1 C5 108.6(2) . . ? C2 N1 C6 125.8(2) . . ? C5 N1 C6 125.5(3) . . ? C2 N3 C4 106.3(2) . . ? C2 N3 C7 123.2(2) . . ? C4 N3 C7 130.5(2) . . ? O2 N4 O1 125.3(2) . . ? O2 N4 C4 118.5(2) . . ? O1 N4 C4 116.1(2) . . ? N3 C2 N1 109.9(2) . . ? C5 C4 N3 109.4(2) . . ? C5 C4 N4 126.3(3) . . ? N3 C4 N4 124.2(2) . . ? C4 C5 N1 105.8(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 C4 N4 O1 6.2(4) . . . . ? C5 C4 N4 O2 -172.2(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C2 H2A O5 0.94(3) 2.18(3) 3.101(4) 167(2) . C2 H2A O6 0.94(3) 2.66(3) 3.273(4) 123(2) . C2 H2A O2 0.94(3) 2.68(3) 3.025(3) 102(2) 4_676 C2 H2A S1 0.94(3) 2.89(3) 3.741(3) 151(2) . C5 H5A O6 0.96(3) 2.26(3) 3.048(4) 138(2) 3_565 C5 H5A O1 0.96(3) 2.71(3) 3.217(4) 113.3(18) 3_465 C7 H7C O4 0.95(3) 2.44(3) 3.170(4) 134(2) 1_455 C6 H6A O4 1.01(3) 2.67(3) 3.362(4) 125.8(19) 2_545 C6 H6A O1 1.01(3) 2.73(3) 3.201(4) 108.6(17) 3_465 C6 H6A O2 1.01(3) 2.65(3) 3.054(4) 103.7(17) 4_676 C6 H6B O6 0.95(3) 2.55(3) 3.384(4) 147(2) 3_565 C6 H6C O6 1.00(3) 2.49(3) 3.379(4) 147(2) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 23.31 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.234 _refine_diff_density_min -0.393 _refine_diff_density_rms 0.064 data_5a _database_code_depnum_ccdc_archive 'CCDC 272563' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '1-ethyl-3-methyl-4-nitroimidazolium triflate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H10 F3 N3 O5 S' _chemical_formula_weight 305.24 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.872(2) _cell_length_b 12.839(3) _cell_length_c 9.5949(19) _cell_angle_alpha 90.00 _cell_angle_beta 96.630(4) _cell_angle_gamma 90.00 _cell_volume 1207.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 854 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 23.27 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.64 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.678 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.329 _exptl_absorpt_correction_type sphere _exptl_absorpt_correction_T_min 0.8554 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '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 5328 _diffrn_reflns_av_R_equivalents 0.0152 _diffrn_reflns_av_sigmaI/netI 0.0143 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 23.27 _reflns_number_total 1735 _reflns_number_gt 1639 _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^)+(0.0314P)^2^+0.6003P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0126(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1735 _refine_ls_number_parameters 213 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0253 _refine_ls_R_factor_gt 0.0240 _refine_ls_wR_factor_ref 0.0631 _refine_ls_wR_factor_gt 0.0623 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.29912(4) 0.52677(3) 0.22786(4) 0.02341(16) Uani 1 1 d . . . F1 F 0.18418(11) 0.40660(9) 0.39881(11) 0.0464(3) Uani 1 1 d . . . F2 F 0.38884(12) 0.36262(8) 0.36985(12) 0.0479(3) Uani 1 1 d . . . F3 F 0.35345(11) 0.49412(8) 0.49908(10) 0.0401(3) Uani 1 1 d . . . O1 O 0.96694(14) 0.21775(12) -0.02272(15) 0.0525(4) Uani 1 1 d . . . O2 O 0.75099(14) 0.18906(10) -0.07722(13) 0.0416(3) Uani 1 1 d . . . O3 O 0.43910(12) 0.55381(10) 0.21967(13) 0.0372(3) Uani 1 1 d . . . O4 O 0.23887(13) 0.45892(10) 0.11863(12) 0.0384(3) Uani 1 1 d . . . O5 O 0.21502(11) 0.61251(9) 0.26062(12) 0.0321(3) Uani 1 1 d . . . N1 N 0.83329(13) 0.46750(10) 0.18809(13) 0.0222(3) Uani 1 1 d . . . N3 N 0.68957(13) 0.35142(10) 0.09765(13) 0.0230(3) Uani 1 1 d . . . N4 N 0.84671(16) 0.23648(11) -0.01561(15) 0.0331(4) Uani 1 1 d . . . C2 C 0.70302(16) 0.43937(13) 0.16972(16) 0.0225(4) Uani 1 1 d . . . H2A H 0.6323(18) 0.4723(13) 0.2007(17) 0.022(4) Uiso 1 1 d . . . C4 C 0.81855(16) 0.32336(12) 0.07015(16) 0.0242(4) Uani 1 1 d . . . C5 C 0.90789(17) 0.39539(13) 0.12644(16) 0.0250(4) Uani 1 1 d . . . H5A H 1.001(2) 0.4019(14) 0.1253(18) 0.029(5) Uiso 1 1 d . . . C6 C 0.88766(19) 0.56162(15) 0.2646(2) 0.0323(4) Uani 1 1 d . . . H6A H 0.8994(19) 0.5451(15) 0.361(2) 0.037(5) Uiso 1 1 d . . . H6B H 0.973(2) 0.5703(15) 0.236(2) 0.038(5) Uiso 1 1 d . . . C7 C 0.7964(2) 0.65392(16) 0.2346(3) 0.0424(5) Uani 1 1 d . . . H7A H 0.707(3) 0.6413(19) 0.266(2) 0.061(7) Uiso 1 1 d . . . H7B H 0.781(2) 0.6676(17) 0.139(3) 0.056(7) Uiso 1 1 d . . . H7C H 0.838(2) 0.7130(18) 0.281(2) 0.048(6) Uiso 1 1 d . . . C8 C 0.55788(19) 0.29746(16) 0.0632(2) 0.0323(4) Uani 1 1 d . . . H8A H 0.490(2) 0.3368(17) 0.103(2) 0.046(6) Uiso 1 1 d . . . H8B H 0.5607(19) 0.2293(17) 0.103(2) 0.039(5) Uiso 1 1 d . . . H8C H 0.537(2) 0.2938(15) -0.036(2) 0.043(5) Uiso 1 1 d . . . C9 C 0.30718(17) 0.44375(13) 0.38259(17) 0.0287(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0207(2) 0.0265(3) 0.0232(2) 0.00419(16) 0.00360(16) 0.00202(16) F1 0.0434(7) 0.0545(7) 0.0423(6) 0.0113(5) 0.0094(5) -0.0193(5) F2 0.0627(8) 0.0323(6) 0.0479(7) 0.0099(5) 0.0025(5) 0.0175(5) F3 0.0463(6) 0.0473(6) 0.0246(5) 0.0002(5) -0.0046(5) -0.0009(5) O1 0.0478(9) 0.0564(9) 0.0544(9) -0.0115(7) 0.0100(7) 0.0246(7) O2 0.0613(9) 0.0309(7) 0.0333(7) -0.0079(6) 0.0080(6) -0.0060(7) O3 0.0234(6) 0.0436(7) 0.0464(8) 0.0123(6) 0.0109(5) 0.0016(5) O4 0.0486(8) 0.0398(7) 0.0255(6) -0.0019(5) -0.0011(5) -0.0015(6) O5 0.0273(6) 0.0325(7) 0.0367(7) 0.0044(5) 0.0050(5) 0.0077(5) N1 0.0212(7) 0.0252(7) 0.0202(7) 0.0002(5) 0.0020(5) 0.0011(6) N3 0.0235(7) 0.0231(7) 0.0225(7) 0.0010(6) 0.0023(5) -0.0004(6) N4 0.0451(10) 0.0291(8) 0.0258(8) 0.0013(6) 0.0065(7) 0.0091(7) C2 0.0206(9) 0.0255(9) 0.0216(8) 0.0011(7) 0.0039(7) 0.0014(7) C4 0.0281(9) 0.0238(9) 0.0210(8) 0.0017(7) 0.0038(7) 0.0059(7) C5 0.0215(9) 0.0311(9) 0.0226(8) 0.0041(7) 0.0028(7) 0.0049(7) C6 0.0271(10) 0.0359(10) 0.0335(11) -0.0089(8) 0.0013(8) -0.0074(8) C7 0.0488(13) 0.0277(11) 0.0485(14) -0.0064(9) -0.0035(10) -0.0041(9) C8 0.0285(10) 0.0296(11) 0.0380(11) -0.0009(9) 0.0010(8) -0.0073(8) C9 0.0287(9) 0.0293(9) 0.0280(9) 0.0024(7) 0.0023(7) -0.0011(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O5 1.4353(12) . ? S1 O3 1.4358(12) . ? S1 O4 1.4377(13) . ? S1 C9 1.8218(17) . ? F1 C9 1.3303(19) . ? F2 C9 1.331(2) . ? F3 C9 1.3260(19) . ? O1 N4 1.221(2) . ? O2 N4 1.2183(19) . ? N1 C2 1.328(2) . ? N1 C5 1.360(2) . ? N1 C6 1.482(2) . ? N3 C2 1.323(2) . ? N3 C4 1.378(2) . ? N3 C8 1.476(2) . ? N4 C4 1.432(2) . ? C4 C5 1.347(2) . ? C6 C7 1.497(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O5 S1 O3 114.28(8) . . ? O5 S1 O4 115.04(8) . . ? O3 S1 O4 115.24(8) . . ? O5 S1 C9 104.01(7) . . ? O3 S1 C9 103.55(7) . . ? O4 S1 C9 102.42(8) . . ? C2 N1 C5 108.77(14) . . ? C2 N1 C6 125.26(14) . . ? C5 N1 C6 125.96(14) . . ? C2 N3 C4 106.50(13) . . ? C2 N3 C8 123.38(14) . . ? C4 N3 C8 130.08(14) . . ? O2 N4 O1 125.39(15) . . ? O2 N4 C4 118.48(14) . . ? O1 N4 C4 116.11(15) . . ? N3 C2 N1 109.81(14) . . ? C5 C4 N3 108.69(14) . . ? C5 C4 N4 127.11(15) . . ? N3 C4 N4 123.96(15) . . ? C4 C5 N1 106.22(14) . . ? N1 C6 C7 111.99(15) . . ? F3 C9 F1 107.85(13) . . ? F3 C9 F2 107.80(13) . . ? F1 C9 F2 107.50(14) . . ? F3 C9 S1 112.33(12) . . ? F1 C9 S1 110.52(11) . . ? F2 C9 S1 110.66(11) . . ? 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 C5 C4 N4 O1 10.7(2) . . . . ? C2 N1 C6 C7 -40.1(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C2 H2A O3 0.896(18) 2.201(19) 3.076(2) 165.4(15) . C6 H6B O5 0.93(2) 2.43(2) 3.302(2) 156.4(16) 1_655 C5 H5A O4 0.921(19) 2.471(19) 3.377(2) 168.0(15) 1_655 C8 H8C F2 0.95(2) 2.59(2) 3.120(2) 115.7(15) 4_565 C6 H6A F1 0.94(2) 2.61(2) 3.410(2) 142.8(15) 3_666 C8 H8C O3 0.95(2) 2.66(2) 3.322(2) 127.0(15) 3_665 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 23.27 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.271 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.038 data_7b _database_code_depnum_ccdc_archive 'CCDC 272564' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '1,2,3 trimethyl-4 nitroimidazolium NTf2' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H10 F6 N4 O6 S2' _chemical_formula_weight 436.32 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' S S 0.1246 0.1234 '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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.113(2) _cell_length_b 12.596(4) _cell_length_c 17.035(5) _cell_angle_alpha 70.065(5) _cell_angle_beta 81.042(5) _cell_angle_gamma 77.570(5) _cell_volume 1591.7(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1007 _cell_measurement_theta_min 2.98 _cell_measurement_theta_max 23.31 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.64 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.821 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.438 _exptl_absorpt_correction_type sphere _exptl_absorpt_correction_T_min 0.8238 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '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 6545 _diffrn_reflns_av_R_equivalents 0.0183 _diffrn_reflns_av_sigmaI/netI 0.0330 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.28 _diffrn_reflns_theta_max 23.36 _reflns_number_total 4389 _reflns_number_gt 3501 _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^)+(0.0415P)^2^+1.1244P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0007(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4389 _refine_ls_number_parameters 550 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0505 _refine_ls_R_factor_gt 0.0355 _refine_ls_wR_factor_ref 0.0924 _refine_ls_wR_factor_gt 0.0839 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S11 S 0.15896(9) 0.27828(6) 0.37888(5) 0.0305(2) Uani 1 1 d . . . S12 S 0.82953(9) 0.72942(6) 0.11806(5) 0.0286(2) Uani 1 1 d . . . S21 S 0.23246(9) 0.20003(6) 0.24034(5) 0.0290(2) Uani 1 1 d . . . S22 S 0.81588(9) 0.80378(6) 0.25588(5) 0.0285(2) Uani 1 1 d . . . F11 F 0.3370(3) 0.11150(17) 0.48918(13) 0.0620(6) Uani 1 1 d . . . F12 F 0.9299(3) 0.90229(18) -0.00281(14) 0.0694(7) Uani 1 1 d . . . F21 F 0.1362(3) 0.06193(17) 0.44932(14) 0.0683(7) Uani 1 1 d . . . F22 F 0.6969(3) 0.94928(15) 0.06292(12) 0.0551(6) Uani 1 1 d . . . F31 F 0.0805(3) 0.16038(19) 0.53329(13) 0.0636(6) Uani 1 1 d . . . F32 F 0.7037(3) 0.85762(18) -0.02155(13) 0.0707(7) Uani 1 1 d . . . F41 F 0.1265(3) 0.31474(18) 0.09364(12) 0.0613(6) Uani 1 1 d . . . F42 F 0.7013(3) 0.7033(2) 0.40820(13) 0.0738(7) Uani 1 1 d . . . F51 F 0.0917(3) 0.41408(15) 0.17610(13) 0.0549(6) Uani 1 1 d . . . F52 F 0.7033(3) 0.61088(18) 0.32553(13) 0.0717(7) Uani 1 1 d . . . F61 F 0.3400(3) 0.36931(16) 0.11873(12) 0.0524(5) Uani 1 1 d . . . F62 F 0.9347(3) 0.61280(19) 0.36987(14) 0.0743(8) Uani 1 1 d . . . O11 O 0.3035(3) 0.76689(19) 0.07132(13) 0.0418(6) Uani 1 1 d . . . O12 O 0.5874(3) 0.40896(18) 0.38463(13) 0.0374(5) Uani 1 1 d . . . O21 O 0.3565(3) 0.58253(18) 0.13052(14) 0.0404(6) Uani 1 1 d . . . O22 O 0.6445(3) 0.22312(18) 0.43358(13) 0.0419(6) Uani 1 1 d . . . O31 O 0.2299(3) 0.35473(17) 0.40370(14) 0.0421(6) Uani 1 1 d . . . O32 O 0.9535(3) 0.66044(18) 0.07858(14) 0.0421(6) Uani 1 1 d . . . O41 O -0.0166(3) 0.3055(2) 0.36595(16) 0.0526(7) Uani 1 1 d . . . O42 O 0.6674(3) 0.69681(17) 0.14574(13) 0.0385(5) Uani 1 1 d . . . O51 O 0.3790(3) 0.13341(17) 0.21114(14) 0.0401(6) Uani 1 1 d . . . O52 O 0.9267(3) 0.85523(18) 0.28320(14) 0.0394(5) Uani 1 1 d . . . O61 O 0.0772(3) 0.15828(18) 0.25834(14) 0.0423(6) Uani 1 1 d . . . O62 O 0.6470(3) 0.86291(18) 0.24250(14) 0.0390(5) Uani 1 1 d . . . N11 N 0.2945(3) 0.66120(19) 0.34778(14) 0.0256(6) Uani 1 1 d . . . N12 N 0.7099(3) 0.3607(2) 0.15646(14) 0.0277(6) Uani 1 1 d . . . N31 N 0.2993(3) 0.79645(18) 0.22823(14) 0.0230(5) Uani 1 1 d . . . N32 N 0.6967(3) 0.21349(18) 0.26889(14) 0.0238(5) Uani 1 1 d . . . N41 N 0.3237(3) 0.6812(2) 0.13253(15) 0.0297(6) Uani 1 1 d . . . N42 N 0.6294(3) 0.3136(2) 0.37594(15) 0.0293(6) Uani 1 1 d . . . N51 N 0.2854(3) 0.2423(2) 0.30869(15) 0.0313(6) Uani 1 1 d . . . N52 N 0.9163(3) 0.7578(2) 0.18345(15) 0.0291(6) Uani 1 1 d . . . C21 C 0.2914(3) 0.7748(2) 0.31141(17) 0.0237(6) Uani 1 1 d . . . C22 C 0.7251(3) 0.2458(2) 0.18491(18) 0.0277(7) Uani 1 1 d . . . C41 C 0.3090(3) 0.6941(2) 0.21400(17) 0.0243(7) Uani 1 1 d . . . C42 C 0.6631(3) 0.3112(2) 0.29127(17) 0.0241(7) Uani 1 1 d . . . C51 C 0.3063(4) 0.6101(3) 0.28788(19) 0.0273(7) Uani 1 1 d . . . H51A H 0.307(3) 0.536(2) 0.3011(17) 0.023(8) Uiso 1 1 d . . . C52 C 0.6712(4) 0.4027(3) 0.22214(18) 0.0271(7) Uani 1 1 d . . . H52A H 0.657(3) 0.482(3) 0.2140(18) 0.028(8) Uiso 1 1 d . . . C61 C 0.2854(5) 0.6009(3) 0.4391(2) 0.0369(8) Uani 1 1 d . . . H61A H 0.188(4) 0.635(3) 0.463(2) 0.043(10) Uiso 1 1 d . . . H61B H 0.286(5) 0.522(4) 0.448(2) 0.071(13) Uiso 1 1 d . . . H61C H 0.383(5) 0.606(3) 0.460(2) 0.057(11) Uiso 1 1 d . . . C62 C 0.7282(5) 0.4325(4) 0.0672(2) 0.0403(9) Uani 1 1 d . . . H62A H 0.825(6) 0.403(4) 0.042(3) 0.081(15) Uiso 1 1 d . . . H62B H 0.736(6) 0.504(4) 0.063(3) 0.095(17) Uiso 1 1 d . . . H62C H 0.636(5) 0.429(3) 0.045(3) 0.074(14) Uiso 1 1 d . . . C71 C 0.2801(4) 0.8590(3) 0.3547(2) 0.0322(7) Uani 1 1 d . . . H71A H 0.283(4) 0.824(3) 0.415(2) 0.053(10) Uiso 1 1 d . . . H71B H 0.178(5) 0.909(3) 0.349(2) 0.051(10) Uiso 1 1 d . . . H71C H 0.370(5) 0.904(3) 0.332(2) 0.071(12) Uiso 1 1 d . . . C72 C 0.7669(5) 0.1692(3) 0.1334(2) 0.0409(9) Uani 1 1 d . . . H72A H 0.859(6) 0.114(4) 0.149(3) 0.078(14) Uiso 1 1 d . . . H72B H 0.685(6) 0.130(4) 0.138(3) 0.080(15) Uiso 1 1 d . . . H72C H 0.793(5) 0.214(4) 0.074(3) 0.090(15) Uiso 1 1 d . . . C81 C 0.2917(5) 0.9119(3) 0.1668(2) 0.0348(8) Uani 1 1 d . . . H81A H 0.299(5) 0.961(3) 0.194(2) 0.058(12) Uiso 1 1 d . . . H81B H 0.394(5) 0.909(3) 0.121(3) 0.071(12) Uiso 1 1 d . . . H81C H 0.186(5) 0.934(3) 0.142(2) 0.062(11) Uiso 1 1 d . . . C82 C 0.7041(5) 0.0936(3) 0.3231(2) 0.0360(8) Uani 1 1 d . . . H82A H 0.601(4) 0.084(3) 0.363(2) 0.049(10) Uiso 1 1 d . . . H82B H 0.715(5) 0.049(3) 0.285(3) 0.066(12) Uiso 1 1 d . . . H82C H 0.797(5) 0.075(3) 0.350(2) 0.060(12) Uiso 1 1 d . . . C91 C 0.1813(4) 0.1449(3) 0.4674(2) 0.0412(8) Uani 1 1 d . . . C92 C 0.7885(4) 0.8673(3) 0.0348(2) 0.0368(8) Uani 1 1 d . . . C101 C 0.1967(4) 0.3326(3) 0.1525(2) 0.0351(8) Uani 1 1 d . . . C102 C 0.7898(4) 0.6734(3) 0.3442(2) 0.0413(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S11 0.0267(4) 0.0334(4) 0.0313(4) -0.0097(3) -0.0045(3) -0.0050(3) S12 0.0312(4) 0.0267(4) 0.0274(4) -0.0082(3) -0.0074(3) -0.0016(3) S21 0.0291(4) 0.0267(4) 0.0326(4) -0.0087(3) -0.0060(3) -0.0069(3) S22 0.0252(4) 0.0344(4) 0.0285(4) -0.0129(3) -0.0020(3) -0.0061(3) F11 0.0519(14) 0.0572(13) 0.0542(14) 0.0124(11) -0.0132(11) -0.0057(10) F12 0.0539(14) 0.0630(14) 0.0590(15) 0.0120(11) 0.0133(11) -0.0073(11) F21 0.1058(19) 0.0512(12) 0.0543(14) -0.0108(11) 0.0044(13) -0.0456(13) F22 0.0715(15) 0.0336(11) 0.0450(12) -0.0078(10) 0.0008(11) 0.0105(10) F31 0.0665(15) 0.0821(15) 0.0385(12) -0.0163(11) 0.0164(11) -0.0254(12) F32 0.110(2) 0.0555(13) 0.0462(13) -0.0074(11) -0.0440(14) -0.0008(13) F41 0.0762(16) 0.0697(14) 0.0432(12) -0.0163(11) -0.0309(12) -0.0082(11) F42 0.0779(17) 0.1026(19) 0.0364(12) -0.0170(13) 0.0129(12) -0.0273(14) F51 0.0640(14) 0.0360(11) 0.0534(13) -0.0092(10) -0.0118(11) 0.0112(10) F52 0.1026(19) 0.0660(14) 0.0536(14) 0.0019(11) -0.0183(13) -0.0558(14) F61 0.0573(13) 0.0475(11) 0.0443(12) -0.0007(10) 0.0017(10) -0.0195(10) F62 0.0498(14) 0.0737(15) 0.0672(16) 0.0209(12) -0.0165(12) -0.0066(11) O11 0.0539(15) 0.0456(14) 0.0242(12) -0.0057(11) -0.0100(11) -0.0089(11) O12 0.0421(13) 0.0383(13) 0.0362(13) -0.0179(11) -0.0056(10) -0.0052(10) O21 0.0512(14) 0.0384(13) 0.0401(13) -0.0224(11) -0.0115(11) -0.0040(10) O22 0.0574(15) 0.0425(13) 0.0242(12) -0.0027(11) -0.0057(11) -0.0172(11) O31 0.0534(15) 0.0366(12) 0.0403(13) -0.0124(10) -0.0081(11) -0.0131(10) O32 0.0486(14) 0.0386(12) 0.0407(13) -0.0217(11) -0.0098(11) 0.0082(10) O41 0.0258(13) 0.0746(17) 0.0609(17) -0.0315(14) -0.0080(12) 0.0035(11) O42 0.0379(13) 0.0429(13) 0.0381(13) -0.0093(11) -0.0104(10) -0.0148(10) O51 0.0359(13) 0.0335(12) 0.0500(14) -0.0156(11) -0.0057(11) 0.0009(10) O52 0.0371(13) 0.0468(13) 0.0445(14) -0.0231(11) -0.0018(11) -0.0160(10) O61 0.0366(13) 0.0447(13) 0.0515(14) -0.0152(11) -0.0074(11) -0.0171(10) O62 0.0254(12) 0.0494(13) 0.0420(13) -0.0202(11) -0.0021(10) 0.0026(10) N11 0.0253(13) 0.0275(13) 0.0230(13) -0.0064(11) -0.0047(11) -0.0032(10) N12 0.0259(14) 0.0338(14) 0.0215(14) -0.0055(12) -0.0060(11) -0.0037(11) N31 0.0224(13) 0.0252(13) 0.0197(13) -0.0053(10) -0.0033(10) -0.0028(10) N32 0.0218(13) 0.0250(13) 0.0237(14) -0.0067(11) -0.0043(10) -0.0023(10) N41 0.0305(15) 0.0348(15) 0.0267(15) -0.0109(13) -0.0073(11) -0.0067(11) N42 0.0274(14) 0.0364(16) 0.0254(14) -0.0062(13) -0.0067(11) -0.0113(11) N51 0.0246(14) 0.0386(14) 0.0307(14) -0.0080(12) -0.0036(11) -0.0096(11) N52 0.0237(13) 0.0356(14) 0.0290(14) -0.0127(12) -0.0010(11) -0.0043(11) C21 0.0176(15) 0.0270(16) 0.0261(16) -0.0096(13) -0.0030(12) -0.0007(11) C22 0.0211(16) 0.0361(18) 0.0284(17) -0.0134(14) -0.0049(13) -0.0030(13) C41 0.0210(15) 0.0284(16) 0.0253(16) -0.0108(14) -0.0053(12) -0.0017(12) C42 0.0220(15) 0.0303(16) 0.0216(16) -0.0072(13) -0.0061(12) -0.0067(12) C51 0.0292(17) 0.0247(17) 0.0299(18) -0.0100(15) -0.0054(13) -0.0045(13) C52 0.0236(16) 0.0305(18) 0.0271(17) -0.0081(15) -0.0042(13) -0.0046(13) C61 0.048(2) 0.037(2) 0.0202(17) -0.0043(15) -0.0030(16) -0.0044(17) C62 0.040(2) 0.050(2) 0.0220(18) -0.0012(16) -0.0022(16) -0.0054(18) C71 0.0317(19) 0.0352(18) 0.031(2) -0.0148(16) -0.0002(15) -0.0041(16) C72 0.041(2) 0.047(2) 0.039(2) -0.0246(19) -0.0008(18) -0.0028(19) C81 0.043(2) 0.0264(17) 0.033(2) -0.0049(16) -0.0075(17) -0.0060(15) C82 0.039(2) 0.0258(17) 0.038(2) -0.0063(16) -0.0037(18) -0.0025(15) C91 0.045(2) 0.046(2) 0.0333(19) -0.0108(16) 0.0084(17) -0.0209(17) C92 0.039(2) 0.0353(18) 0.0313(18) -0.0079(15) -0.0057(16) 0.0005(15) C101 0.0361(19) 0.0352(18) 0.0346(19) -0.0106(15) -0.0089(15) -0.0043(15) C102 0.039(2) 0.054(2) 0.0321(19) -0.0098(17) -0.0029(16) -0.0168(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S11 O31 1.424(2) . ? S11 O41 1.425(2) . ? S11 N51 1.573(3) . ? S11 C91 1.832(3) . ? S12 O42 1.424(2) . ? S12 O32 1.425(2) . ? S12 N52 1.577(2) . ? S12 C92 1.832(3) . ? S21 O61 1.418(2) . ? S21 O51 1.427(2) . ? S21 N51 1.581(3) . ? S21 C101 1.826(3) . ? S22 O62 1.423(2) . ? S22 O52 1.426(2) . ? S22 N52 1.579(3) . ? S22 C102 1.836(3) . ? F11 C91 1.312(4) . ? F12 C92 1.311(4) . ? F21 C91 1.320(4) . ? F22 C92 1.321(4) . ? F31 C91 1.326(4) . ? F32 C92 1.316(4) . ? F41 C101 1.330(4) . ? F42 C102 1.329(4) . ? F51 C101 1.319(4) . ? F52 C102 1.301(4) . ? F61 C101 1.319(4) . ? F62 C102 1.305(4) . ? O11 N41 1.220(3) . ? O12 N42 1.230(3) . ? O21 N41 1.226(3) . ? O22 N42 1.221(3) . ? N11 C21 1.348(3) . ? N11 C51 1.362(4) . ? N11 C61 1.478(4) . ? N12 C22 1.345(4) . ? N12 C52 1.361(4) . ? N12 C62 1.484(4) . ? N31 C21 1.342(4) . ? N31 C41 1.375(4) . ? N31 C81 1.469(4) . ? N32 C22 1.344(4) . ? N32 C42 1.370(4) . ? N32 C82 1.471(4) . ? N41 C41 1.435(4) . ? N42 C42 1.435(4) . ? C21 C71 1.466(4) . ? C22 C72 1.470(5) . ? C41 C51 1.341(4) . ? C42 C52 1.342(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O31 S11 O41 118.61(15) . . ? O31 S11 N51 108.02(14) . . ? O41 S11 N51 116.88(14) . . ? O31 S11 C91 104.34(15) . . ? O41 S11 C91 104.99(15) . . ? N51 S11 C91 101.74(15) . . ? O42 S12 O32 118.23(14) . . ? O42 S12 N52 116.04(13) . . ? O32 S12 N52 108.61(13) . . ? O42 S12 C92 104.70(14) . . ? O32 S12 C92 103.68(15) . . ? N52 S12 C92 103.64(14) . . ? O61 S21 O51 118.32(13) . . ? O61 S21 N51 116.98(14) . . ? O51 S21 N51 108.02(13) . . ? O61 S21 C101 104.97(14) . . ? O51 S21 C101 104.04(14) . . ? N51 S21 C101 102.35(14) . . ? O62 S22 O52 118.42(14) . . ? O62 S22 N52 116.39(13) . . ? O52 S22 N52 107.95(13) . . ? O62 S22 C102 103.95(15) . . ? O52 S22 C102 104.03(14) . . ? N52 S22 C102 104.25(15) . . ? C21 N11 C51 109.9(2) . . ? C21 N11 C61 125.2(3) . . ? C51 N11 C61 124.9(3) . . ? C22 N12 C52 109.7(2) . . ? C22 N12 C62 125.8(3) . . ? C52 N12 C62 124.5(3) . . ? C21 N31 C41 107.8(2) . . ? C21 N31 C81 123.7(3) . . ? C41 N31 C81 128.4(3) . . ? C22 N32 C42 107.2(2) . . ? C22 N32 C82 124.1(3) . . ? C42 N32 C82 128.8(3) . . ? O11 N41 O21 125.0(3) . . ? O11 N41 C41 119.0(2) . . ? O21 N41 C41 116.0(2) . . ? O22 N42 O12 124.7(3) . . ? O22 N42 C42 119.1(2) . . ? O12 N42 C42 116.2(2) . . ? S11 N51 S21 124.49(15) . . ? S12 N52 S22 124.13(15) . . ? N31 C21 N11 107.2(2) . . ? N31 C21 C71 126.5(3) . . ? N11 C21 C71 126.3(3) . . ? N32 C22 N12 107.8(3) . . ? N32 C22 C72 126.1(3) . . ? N12 C22 C72 126.1(3) . . ? C51 C41 N31 108.9(3) . . ? C51 C41 N41 126.5(3) . . ? N31 C41 N41 124.6(2) . . ? C52 C42 N32 109.4(3) . . ? C52 C42 N42 125.9(3) . . ? N32 C42 N42 124.7(2) . . ? C41 C51 N11 106.2(3) . . ? C42 C52 N12 106.0(3) . . ? F11 C91 F21 108.8(3) . . ? F11 C91 F31 107.9(3) . . ? F21 C91 F31 107.5(3) . . ? F11 C91 S11 112.0(2) . . ? F21 C91 S11 110.8(2) . . ? F31 C91 S11 109.7(2) . . ? F12 C92 F32 108.4(3) . . ? F12 C92 F22 107.3(3) . . ? F32 C92 F22 106.9(3) . . ? F12 C92 S12 111.4(2) . . ? F32 C92 S12 110.0(2) . . ? F22 C92 S12 112.7(2) . . ? F51 C101 F61 108.9(3) . . ? F51 C101 F41 107.1(3) . . ? F61 C101 F41 108.2(3) . . ? F51 C101 S21 111.3(2) . . ? F61 C101 S21 111.4(2) . . ? F41 C101 S21 109.8(2) . . ? F52 C102 F62 110.3(3) . . ? F52 C102 F42 106.5(3) . . ? F62 C102 F42 107.4(3) . . ? F52 C102 S22 111.3(2) . . ? F62 C102 S22 112.2(2) . . ? F42 C102 S22 108.8(2) . . ? 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 C51 C41 N41 O11 171.1(3) . . . . ? C51 C41 N41 O21 -8.9(4) . . . . ? N31 C41 N41 O11 -10.6(4) . . . . ? N31 C41 N41 O21 169.4(3) . . . . ? C52 C42 N42 O12 8.0(4) . . . . ? C52 C42 N42 O22 -171.8(3) . . . . ? N32 C42 N42 O12 -174.0(2) . . . . ? N32 C42 N42 O22 6.3(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C51 H51A O31 0.88(3) 2.49(3) 3.283(4) 149(2) . C61 H61B O31 0.96(4) 2.60(4) 3.485(5) 153(3) . C61 H61C O12 0.94(4) 2.64(4) 3.279(4) 126(3) 2_666 C71 H71A O22 0.96(4) 2.58(4) 3.510(4) 161(3) 2_666 C71 H71C O62 0.98(4) 2.57(4) 3.278(4) 130(3) . C81 H81A O51 0.89(4) 2.52(4) 3.363(4) 157(3) 1_565 C81 H81B F22 1.05(4) 2.59(4) 3.527(4) 149(3) . C81 H81C F12 0.96(4) 2.76(4) 3.501(4) 134(3) ? C52 H52A O42 0.94(3) 2.57(3) 3.478(4) 162(2) . C62 H62A F41 0.91(5) 2.61(4) 3.283(5) 131(4) 1_655 C62 H62C F61 0.91(4) 2.66(4) 3.326(5) 131(3) . C72 H72B O51 0.89(4) 2.59(4) 3.281(5) 135(4) . C72 H72C O11 0.99(5) 2.62(5) 3.412(4) 136(3) 2_665 C82 H82B O52 0.97(4) 2.67(4) 3.379(4) 130(3) 1_545 C72 H72C O11 0.99(5) 2.62(5) 3.412(4) 136(3) 2_665 C62 H62C F61 0.91(4) 2.66(4) 3.326(5) 131(3) . _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 23.36 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 0.384 _refine_diff_density_min -0.291 _refine_diff_density_rms 0.052 data_10a _database_code_depnum_ccdc_archive 'CCDC 272565' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '1,3-dimethyl-2-nitroimidazolium triflate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H8 F3 N3 O5 S' _chemical_formula_weight 291.21 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.882(3) _cell_length_b 11.924(5) _cell_length_c 13.324(6) _cell_angle_alpha 90.00 _cell_angle_beta 96.911(6) _cell_angle_gamma 90.00 _cell_volume 1085.4(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 941 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 23.27 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.86 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.782 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.362 _exptl_absorpt_correction_type sphere _exptl_absorpt_correction_T_min 0.7954 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '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 4726 _diffrn_reflns_av_R_equivalents 0.0265 _diffrn_reflns_av_sigmaI/netI 0.0286 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 23.31 _reflns_number_total 1561 _reflns_number_gt 1466 _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^)+(0.0336P)^2^+0.7883P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0062(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1561 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0328 _refine_ls_R_factor_gt 0.0308 _refine_ls_wR_factor_ref 0.0822 _refine_ls_wR_factor_gt 0.0808 _refine_ls_goodness_of_fit_ref 1.141 _refine_ls_restrained_S_all 1.141 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.76371(8) 0.26196(4) 0.13295(4) 0.0269(2) Uani 1 1 d . . . F1 F 0.3836(2) 0.24186(12) 0.08093(12) 0.0460(4) Uani 1 1 d . . . F2 F 0.5494(2) 0.09221(11) 0.06287(12) 0.0469(4) Uani 1 1 d . . . F3 F 0.5558(2) 0.22751(12) -0.04261(10) 0.0438(4) Uani 1 1 d . . . O1 O -0.0512(3) 0.62459(13) 0.10094(12) 0.0395(4) Uani 1 1 d . . . O2 O -0.2375(2) 0.61659(13) 0.22164(13) 0.0391(4) Uani 1 1 d . . . O3 O 0.7286(3) 0.23193(15) 0.23373(13) 0.0514(5) Uani 1 1 d . . . O4 O 0.9244(2) 0.20629(16) 0.09577(15) 0.0490(5) Uani 1 1 d . . . O5 O 0.7487(2) 0.38025(12) 0.11197(12) 0.0359(4) Uani 1 1 d . . . N1 N 0.2035(3) 0.47239(14) 0.20258(13) 0.0251(4) Uani 1 1 d . . . N3 N 0.0039(3) 0.45473(14) 0.31806(13) 0.0255(4) Uani 1 1 d . . . N4 N -0.0929(3) 0.58998(14) 0.18179(14) 0.0285(4) Uani 1 1 d . . . C2 C 0.0378(3) 0.50881(16) 0.23418(15) 0.0231(5) Uani 1 1 d . . . C4 C 0.1532(3) 0.37983(17) 0.33968(17) 0.0294(5) Uani 1 1 d . . . H4A H 0.153(3) 0.333(2) 0.3951(19) 0.029(6) Uiso 1 1 d . . . C5 C 0.2768(4) 0.39063(18) 0.26912(17) 0.0291(5) Uani 1 1 d . . . H5A H 0.392(4) 0.354(2) 0.2591(17) 0.028(6) Uiso 1 1 d . . . C6 C 0.3013(4) 0.5112(2) 0.1158(2) 0.0369(6) Uani 1 1 d . . . H6A H 0.318(3) 0.590(2) 0.1207(18) 0.034(6) Uiso 1 1 d . . . H6B H 0.430(4) 0.473(2) 0.119(2) 0.048(7) Uiso 1 1 d . . . H6C H 0.220(4) 0.492(2) 0.052(2) 0.053(8) Uiso 1 1 d . . . C7 C -0.1602(4) 0.4668(2) 0.3782(2) 0.0375(6) Uani 1 1 d . . . H7A H -0.134(4) 0.415(2) 0.435(2) 0.048(7) Uiso 1 1 d . . . H7B H -0.279(4) 0.448(2) 0.339(2) 0.046(7) Uiso 1 1 d . . . H7C H -0.162(4) 0.545(3) 0.403(2) 0.050(8) Uiso 1 1 d . . . C8 C 0.5522(3) 0.20383(18) 0.05468(17) 0.0288(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0310(4) 0.0176(3) 0.0302(3) 0.0007(2) -0.0047(2) -0.0009(2) F1 0.0276(8) 0.0464(9) 0.0649(10) -0.0158(7) 0.0085(7) -0.0006(6) F2 0.0542(9) 0.0199(7) 0.0665(10) -0.0095(6) 0.0067(7) -0.0106(6) F3 0.0509(9) 0.0488(9) 0.0296(8) -0.0050(6) -0.0040(6) -0.0078(7) O1 0.0539(11) 0.0285(9) 0.0346(10) 0.0081(7) -0.0014(8) 0.0041(7) O2 0.0351(10) 0.0316(9) 0.0497(10) -0.0054(8) 0.0007(8) 0.0096(7) O3 0.0787(14) 0.0416(11) 0.0313(9) 0.0067(8) -0.0042(9) -0.0152(9) O4 0.0301(10) 0.0419(10) 0.0733(13) -0.0101(9) -0.0016(9) 0.0055(8) O5 0.0456(10) 0.0164(8) 0.0426(10) 0.0007(7) -0.0069(8) -0.0039(6) N1 0.0306(10) 0.0174(9) 0.0268(9) -0.0031(7) 0.0012(8) -0.0007(7) N3 0.0308(10) 0.0179(9) 0.0271(9) -0.0014(7) 0.0009(8) -0.0045(8) N4 0.0335(11) 0.0160(9) 0.0336(11) -0.0038(8) -0.0053(9) 0.0000(8) C2 0.0276(12) 0.0145(10) 0.0257(11) -0.0026(8) -0.0023(9) -0.0014(8) C4 0.0404(14) 0.0150(11) 0.0302(12) 0.0015(10) -0.0061(11) -0.0017(9) C5 0.0318(13) 0.0190(11) 0.0344(12) -0.0034(9) -0.0053(10) 0.0045(10) C6 0.0456(16) 0.0304(14) 0.0368(14) 0.0004(11) 0.0131(12) 0.0014(12) C7 0.0352(15) 0.0397(15) 0.0384(14) 0.0003(13) 0.0080(12) -0.0069(11) C8 0.0300(13) 0.0220(11) 0.0344(12) -0.0048(9) 0.0047(10) -0.0019(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O4 1.4286(19) . ? S1 O3 1.4380(19) . ? S1 O5 1.4392(17) . ? S1 C8 1.823(2) . ? F1 C8 1.331(3) . ? F2 C8 1.336(3) . ? F3 C8 1.330(3) . ? O1 N4 1.220(2) . ? O2 N4 1.224(2) . ? N1 C2 1.335(3) . ? N1 C5 1.372(3) . ? N1 C6 1.480(3) . ? N3 C2 1.335(3) . ? N3 C4 1.366(3) . ? N3 C7 1.468(3) . ? N4 C2 1.443(3) . ? C4 C5 1.348(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 S1 O3 115.60(12) . . ? O4 S1 O5 115.38(11) . . ? O3 S1 O5 114.16(10) . . ? O4 S1 C8 102.89(11) . . ? O3 S1 C8 103.14(11) . . ? O5 S1 C8 103.16(10) . . ? C2 N1 C5 106.81(18) . . ? C2 N1 C6 129.10(19) . . ? C5 N1 C6 124.1(2) . . ? C2 N3 C4 106.84(18) . . ? C2 N3 C7 129.27(19) . . ? C4 N3 C7 123.9(2) . . ? O1 N4 O2 125.81(19) . . ? O1 N4 C2 117.06(18) . . ? O2 N4 C2 117.11(18) . . ? N1 C2 N3 110.42(18) . . ? N1 C2 N4 124.90(18) . . ? N3 C2 N4 124.58(18) . . ? C5 C4 N3 108.2(2) . . ? C4 C5 N1 107.7(2) . . ? F3 C8 F1 107.63(19) . . ? F3 C8 F2 107.06(17) . . ? F1 C8 F2 107.23(17) . . ? F3 C8 S1 111.70(15) . . ? F1 C8 S1 112.43(15) . . ? F2 C8 S1 110.53(16) . . ? 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 C2 N4 O1 2.6(3) . . . . ? N3 C2 N4 O1 -173.23(19) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C6 H6B O5 1.00(3) 2.46(3) 3.458(3) 175(2) . C7 H7C O4 0.99(3) 2.53(3) 3.282(3) 133(2) 2_655 C7 H7A O4 0.98(3) 2.58(3) 3.549(3) 174(2) 4_466 C4 H4A O1 0.92(2) 2.59(2) 3.243(3) 128.3(18) 2_545 C6 H6C O1 0.98(3) 2.62(3) 3.567(3) 161(2) 3_565 C6 H6A O3 0.94(3) 2.63(3) 3.330(3) 131.9(18) 2_655 C6 H6A F3 0.94(3) 2.61(3) 3.443(3) 147.5(19) 3_665 C6 H6B O5 1.00(3) 2.46(3) 3.458(3) 175(2) . C6 H6C O5 0.98(3) 2.70(3) 3.279(3) 118(2) 3_665 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 23.31 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.249 _refine_diff_density_min -0.355 _refine_diff_density_rms 0.049 data_13b _database_code_depnum_ccdc_archive 'CCDC 272566' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '1,3-dimethyl-4,5-dicyanoimidazolium methylsulfate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H10 N4 O4 S' _chemical_formula_weight 258.26 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 Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.4703(14) _cell_length_b 7.9000(13) _cell_length_c 8.9145(15) _cell_angle_alpha 90.00 _cell_angle_beta 111.568(3) _cell_angle_gamma 90.00 _cell_volume 554.75(16) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 822 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 23.28 _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.66 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.546 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.302 _exptl_absorpt_correction_type sphere _exptl_absorpt_correction_T_min 0.8358 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '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 2579 _diffrn_reflns_av_R_equivalents 0.0151 _diffrn_reflns_av_sigmaI/netI 0.0266 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 23.29 _reflns_number_total 1552 _reflns_number_gt 1438 _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 fullcycle _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0717P)^2^+0.0628P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.21(11) _refine_ls_number_reflns 1552 _refine_ls_number_parameters 209 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0379 _refine_ls_R_factor_gt 0.0340 _refine_ls_wR_factor_ref 0.0986 _refine_ls_wR_factor_gt 0.0965 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _refine_ls_shift/su_max 0.023 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.26141(8) 1.37136(11) 0.35585(9) 0.0307(3) Uani 1 1 d . . . O1 O 0.3120(6) 1.5210(6) 0.4298(6) 0.0348(12) Uani 0.50 1 d P A 1 O2 O 0.2197(7) 1.2348(6) 0.4506(6) 0.0382(13) Uani 0.50 1 d P A 1 O3 O 0.4300(6) 1.2779(6) 0.3394(6) 0.0329(12) Uani 0.50 1 d P A 1 O1A O 0.2200(6) 1.5283(7) 0.4345(6) 0.0339(12) Uani 0.50 1 d P A 2 O2A O 0.3303(7) 1.2451(6) 0.4715(6) 0.0370(13) Uani 0.50 1 d P A 2 O3A O 0.4213(6) 1.4594(6) 0.3223(5) 0.0265(10) Uani 0.50 1 d P A 2 O4 O 0.1395(3) 1.3553(5) 0.1968(3) 0.0516(8) Uani 1 1 d . A . N1 N 0.1415(3) 0.8615(4) 0.3195(3) 0.0236(6) Uani 1 1 d . . . N3 N 0.3299(3) 0.8523(4) 0.2099(3) 0.0226(6) Uani 1 1 d . . . N4 N 0.2039(5) 0.6009(5) -0.1347(5) 0.0505(11) Uani 1 1 d . . . N5 N -0.2140(5) 0.6174(5) 0.1078(4) 0.0391(9) Uani 1 1 d . . . C2 C 0.2965(4) 0.9100(4) 0.3335(4) 0.0225(8) Uani 1 1 d . . . H2A H 0.376(4) 0.982(4) 0.418(4) 0.008(7) Uiso 1 1 d . . . C4 C 0.1918(4) 0.7600(4) 0.1118(4) 0.0245(8) Uani 1 1 d . . . C5 C 0.0746(4) 0.7653(4) 0.1817(4) 0.0231(7) Uani 1 1 d . . . C6 C 0.0653(6) 0.8886(8) 0.4412(5) 0.0395(10) Uani 1 1 d . . . H6A H -0.032(5) 0.909(5) 0.395(5) 0.040(13) Uiso 1 1 d . . . H6B H 0.114(6) 0.805(6) 0.520(6) 0.055(15) Uiso 1 1 d . . . H6C H 0.138(8) 0.986(10) 0.495(8) 0.11(2) Uiso 1 1 d . . . C7 C 0.4892(4) 0.8792(8) 0.1823(5) 0.0386(9) Uani 1 1 d . . . H7A H 0.564(5) 0.938(5) 0.265(5) 0.037(11) Uiso 1 1 d . . . H7B H 0.534(7) 0.767(7) 0.175(6) 0.070(16) Uiso 1 1 d . . . H7C H 0.462(5) 0.936(5) 0.080(6) 0.045(12) Uiso 1 1 d . . . C8 C 0.1938(4) 0.6727(5) -0.0277(4) 0.0324(8) Uani 1 1 d . . . C9 C -0.0871(5) 0.6837(5) 0.1371(4) 0.0310(8) Uani 1 1 d . . . C10 C 0.5035(4) 1.3554(8) 0.2468(4) 0.0468(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0247(4) 0.0367(5) 0.0316(5) 0.0034(5) 0.0114(3) 0.0013(5) O1 0.039(3) 0.026(3) 0.036(3) -0.008(2) 0.010(3) -0.002(2) O2 0.053(3) 0.027(3) 0.050(3) 0.001(2) 0.037(3) 0.006(3) O3 0.037(3) 0.030(3) 0.038(3) 0.007(2) 0.021(2) 0.002(2) O1A 0.041(3) 0.028(3) 0.041(3) 0.008(2) 0.024(3) 0.012(2) O2A 0.051(3) 0.020(3) 0.048(3) 0.005(2) 0.029(3) 0.003(2) O3A 0.023(2) 0.027(2) 0.029(3) 0.000(2) 0.008(2) -0.005(2) O4 0.0269(12) 0.075(2) 0.0451(14) -0.0212(19) 0.0044(11) -0.005(2) N1 0.0240(12) 0.0254(14) 0.0210(12) 0.0027(15) 0.0078(10) 0.0048(17) N3 0.0196(12) 0.0235(14) 0.0235(13) 0.0003(14) 0.0064(10) -0.0051(15) N4 0.038(2) 0.072(3) 0.041(2) -0.024(2) 0.0142(18) 0.0068(19) N5 0.0242(19) 0.045(2) 0.046(2) -0.0010(17) 0.0104(17) -0.0082(16) C2 0.0236(17) 0.018(2) 0.0225(18) 0.0028(14) 0.0049(14) 0.0013(13) C4 0.0225(17) 0.0271(18) 0.0237(17) -0.0007(16) 0.0082(15) 0.0034(15) C5 0.0207(17) 0.0224(16) 0.0243(17) 0.0058(16) 0.0062(14) 0.0000(15) C6 0.030(2) 0.064(3) 0.027(2) 0.005(2) 0.0120(17) 0.009(3) C7 0.0219(16) 0.064(3) 0.033(2) -0.005(3) 0.0127(15) -0.008(2) C8 0.0191(17) 0.041(2) 0.033(2) -0.0028(19) 0.0057(15) 0.0055(16) C9 0.027(2) 0.034(2) 0.0299(19) -0.0011(16) 0.0079(15) 0.0022(18) C10 0.0355(18) 0.069(3) 0.042(2) -0.015(3) 0.0209(16) -0.012(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.345(5) . ? S1 O2A 1.399(5) . ? S1 O4 1.420(3) . ? S1 O2 1.490(5) . ? S1 O1A 1.527(5) . ? S1 O3A 1.645(4) . ? S1 O3 1.661(5) . ? O3 C10 1.350(6) . ? O3A C10 1.399(6) . ? N1 C2 1.329(4) . ? N1 C5 1.377(4) . ? N1 C6 1.468(4) . ? N3 C2 1.315(4) . ? N3 C4 1.383(4) . ? N3 C7 1.474(4) . ? N4 C8 1.140(5) . ? N5 C9 1.137(5) . ? C4 C5 1.353(4) . ? C4 C8 1.427(5) . ? C5 C9 1.432(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 O2A 107.1(2) . . ? O1 S1 O4 123.5(3) . . ? O2A S1 O4 128.7(3) . . ? O1 S1 O2 117.2(3) . . ? O2A S1 O2 35.7(2) . . ? O4 S1 O2 105.3(3) . . ? O1 S1 O1A 31.4(2) . . ? O2A S1 O1A 110.2(3) . . ? O4 S1 O1A 109.0(2) . . ? O2 S1 O1A 100.70(19) . . ? O1 S1 O3A 65.3(2) . . ? O2A S1 O3A 106.7(3) . . ? O4 S1 O3A 101.6(2) . . ? O2 S1 O3A 142.3(2) . . ? O1A S1 O3A 94.8(2) . . ? O1 S1 O3 107.8(3) . . ? O2A S1 O3 67.0(2) . . ? O4 S1 O3 101.8(2) . . ? O2 S1 O3 96.8(3) . . ? O1A S1 O3 138.69(19) . . ? O3A S1 O3 51.69(16) . . ? C10 O3 S1 117.2(4) . . ? C10 O3A S1 115.3(3) . . ? C2 N1 C5 108.2(2) . . ? C2 N1 C6 125.2(3) . . ? C5 N1 C6 126.2(3) . . ? C2 N3 C4 108.7(2) . . ? C2 N3 C7 125.6(3) . . ? C4 N3 C7 125.7(3) . . ? N3 C2 N1 109.3(3) . . ? C5 C4 N3 106.6(3) . . ? C5 C4 C8 131.4(3) . . ? N3 C4 C8 121.9(3) . . ? C4 C5 N1 107.3(3) . . ? C4 C5 C9 130.3(3) . . ? N1 C5 C9 122.3(3) . . ? N4 C8 C4 176.4(4) . . ? N5 C9 C5 177.3(4) . . ? O3 C10 O3A 63.2(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C2 H2A O2A 0.98(3) 2.20(3) 2.888(6) 126(2) . C2 H2A O1 0.98(3) 2.51(3) 3.328(6) 141(2) 2_646 C2 H2A O3 0.98(3) 2.53(3) 3.112(6) 118(2) . C2 H2A O3A 0.98(3) 2.33(3) 3.144(6) 140(2) 2_646 C2 H2A O2 0.98(3) 2.47(3) 2.931(6) 108.2(19) . C6 H6C O2 0.99(7) 2.17(8) 3.019(8) 143(6) . C6 H6A N4 0.79(4) 2.70(4) 3.301(7) 134(4) 2 C7 H7A O1 0.91(4) 2.61(4) 3.430(7) 150(3) 2_646 C7 H7C N5 0.96(5) 2.59(4) 3.351(6) 136(3) 2 C7 H7B N5 0.97(6) 2.69(6) 3.502(6) 141(4) 1_655 C2 H2A O2A 0.98(3) 2.20(3) 2.888(6) 126(2) . C6 H6B O1A 0.94(5) 2.59(5) 3.144(8) 118(4) 1_545 C7 H7A O2A 0.91(4) 2.67(4) 3.084(7) 109(3) 2_646 C6 H6C O2A 0.99(7) 2.67(7) 3.549(8) 147(5) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 23.29 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.346 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.049