Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Mimoza Gjikaj' _publ_contact_author_address ; Institut of Inorganic and Analytical Chemistry TU Clausthal Paul-Ernst-Strasse 4 Clausthal-Zellerfeld 38678 GERMANY ; _publ_contact_author_email MIMOZA.GJIKAJ@TU-CLAUSTHAL.DE _publ_section_title ; Crown-ether enclosure generated by ionic liquid components- Synthesis, crystal structure and Raman spectra of compounds of imidazolium based salts and 18-crown-6 ; loop_ _publ_author_name 'Mimoza Gjikaj' 'Arnold Adam' 'Wolfgang Brockner' 'Jan Namyslo' data_1 _database_code_depnum_ccdc_archive 'CCDC 648112' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '1,3-dimethylimidazolium methylsulfate (18-crown-6)' _chemical_melting_point ? _chemical_formula_moiety 'C24 H48 N4 O14 S2' _chemical_formula_sum 'C24 H48 N4 O14 S2' _chemical_formula_weight 680.78 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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5511(18) _cell_length_b 9.298(2) _cell_length_c 10.774(3) _cell_angle_alpha 86.929(18) _cell_angle_beta 80.092(18) _cell_angle_gamma 82.061(17) _cell_volume 835.3(3) _cell_formula_units_Z 1 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 25.02 _exptl_crystal_description cubic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.353 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 364 _exptl_absorpt_coefficient_mu 0.228 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 'IPDS II (Stoe & Cie)' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean 'not measured' _diffrn_standards_number 'not measured' _diffrn_standards_interval_count 'not measured' _diffrn_standards_interval_time 'not measured' _diffrn_standards_decay_% 'not measured' _diffrn_reflns_number 8892 _diffrn_reflns_av_R_equivalents 0.0509 _diffrn_reflns_av_sigmaI/netI 0.0431 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2903 _reflns_number_gt 2183 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0893P)^2^+0.6952P] 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 0.006(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2903 _refine_ls_number_parameters 293 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0845 _refine_ls_R_factor_gt 0.0621 _refine_ls_wR_factor_ref 0.1682 _refine_ls_wR_factor_gt 0.1542 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 0.35824(11) 0.31940(9) 0.81850(8) 0.0412(3) Uani 1 1 d . . . O1 O 0.4028(5) 0.4384(4) 0.7427(4) 0.1051(15) Uani 1 1 d . . . O2 O 0.4772(5) 0.2414(4) 0.8802(4) 0.0990(13) Uani 1 1 d . . . O3 O 0.2901(5) 0.2222(5) 0.7502(4) 0.0985(13) Uani 1 1 d . . . O4 O 0.2070(4) 0.3764(4) 0.9169(3) 0.0837(11) Uani 1 1 d . . . O5 O 0.8723(3) 0.1121(3) 0.7355(2) 0.0505(7) Uani 1 1 d . . . O6 O 0.9257(3) 0.3046(3) 0.5185(3) 0.0530(7) Uani 1 1 d . . . O7 O 0.9678(3) 0.1787(3) 0.2744(3) 0.0579(7) Uani 1 1 d . . . N1 N 0.5054(3) -0.1455(3) 0.7328(3) 0.0402(7) Uani 1 1 d . . . N3 N 0.6688(3) -0.0943(3) 0.5659(3) 0.0348(6) Uani 1 1 d . . . C2 C 0.5884(4) -0.0436(4) 0.6738(3) 0.0375(8) Uani 1 1 d . . . C4 C 0.6342(5) -0.2323(4) 0.5543(4) 0.0451(9) Uani 1 1 d . . . C5 C 0.5336(5) -0.2647(4) 0.6582(4) 0.0486(9) Uani 1 1 d . . . C6 C 0.3989(6) -0.1294(7) 0.8549(4) 0.0626(12) Uani 1 1 d . . . C7 C 0.7799(5) -0.0176(5) 0.4753(4) 0.0442(8) Uani 1 1 d . . . C8 C 0.2371(11) 0.4827(7) 1.0031(6) 0.099(2) Uani 1 1 d . . . C9 C 0.8713(6) 0.2636(5) 0.7421(5) 0.0625(12) Uani 1 1 d . . . C10 C 0.8133(5) 0.3375(4) 0.6306(5) 0.0644(13) Uani 1 1 d . . . C11 C 0.8738(6) 0.3769(5) 0.4116(5) 0.0663(13) Uani 1 1 d . . . C12 C 0.9824(6) 0.3253(5) 0.2966(5) 0.0667(13) Uani 1 1 d . . . C13 C 0.9269(6) -0.1236(6) 0.8312(4) 0.0640(12) Uani 1 1 d . . . C14 C 0.9344(6) 0.0335(6) 0.8385(4) 0.0653(13) Uani 1 1 d . . . H2 H 0.590(4) 0.038(4) 0.702(3) 0.041(10) Uiso 1 1 d . . . H4 H 0.674(4) -0.282(4) 0.487(4) 0.041(10) Uiso 1 1 d . . . H5 H 0.494(6) -0.343(5) 0.678(4) 0.064(13) Uiso 1 1 d . . . H61 H 0.441(7) -0.190(6) 0.908(6) 0.090(18) Uiso 1 1 d . . . H62 H 0.297(8) -0.156(6) 0.850(5) 0.098(19) Uiso 1 1 d . . . H63 H 0.385(7) -0.028(8) 0.881(6) 0.11(2) Uiso 1 1 d . . . H71 H 0.746(8) -0.002(7) 0.409(6) 0.10(2) Uiso 1 1 d . . . H72 H 0.801(6) 0.065(6) 0.508(5) 0.080(15) Uiso 1 1 d . . . H73 H 0.879(8) -0.075(7) 0.457(6) 0.11(2) Uiso 1 1 d . . . H81 H 0.344(5) 0.461(4) 1.031(4) 0.040(11) Uiso 1 1 d . . . H82 H 0.2898 0.5780 0.9643 0.24(5) Uiso 1 1 d . . . H83 H 0.129(8) 0.517(7) 1.051(6) 0.10(2) Uiso 1 1 d . . . H91 H 0.984(6) 0.285(5) 0.746(4) 0.066(13) Uiso 1 1 d . . . H92 H 0.786(7) 0.303(6) 0.821(5) 0.097(17) Uiso 1 1 d . . . H101 H 0.716(6) 0.312(5) 0.627(4) 0.065(13) Uiso 1 1 d . . . H102 H 0.789(6) 0.439(6) 0.645(4) 0.072(13) Uiso 1 1 d . . . H111 H 0.764(6) 0.354(5) 0.402(4) 0.072(13) Uiso 1 1 d . . . H112 H 0.876(6) 0.484(6) 0.416(5) 0.090(16) Uiso 1 1 d . . . H121 H 0.969(7) 0.386(6) 0.225(6) 0.100(18) Uiso 1 1 d . . . H122 H 1.100(6) 0.328(5) 0.298(4) 0.065(12) Uiso 1 1 d . . . H131 H 0.950(6) -0.170(6) 0.911(5) 0.088(16) Uiso 1 1 d . . . H132 H 0.821(6) -0.145(5) 0.828(4) 0.073(14) Uiso 1 1 d . . . H141 H 0.882(6) 0.064(5) 0.911(5) 0.079(15) Uiso 1 1 d . . . H142 H 1.044(6) 0.056(5) 0.841(4) 0.059(12) 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 0.0450(5) 0.0398(5) 0.0385(5) 0.0018(3) -0.0077(4) -0.0047(4) O1 0.109(3) 0.075(2) 0.112(3) 0.040(2) 0.023(2) -0.013(2) O2 0.103(3) 0.098(3) 0.101(3) 0.003(2) -0.058(2) 0.020(2) O3 0.093(3) 0.111(3) 0.100(3) -0.044(2) -0.022(2) -0.022(2) O4 0.081(2) 0.079(2) 0.083(2) -0.0190(19) 0.0231(19) -0.0211(19) O5 0.0495(15) 0.0590(16) 0.0458(14) -0.0182(12) -0.0059(12) -0.0131(12) O6 0.0428(14) 0.0372(13) 0.0802(19) 0.0009(13) -0.0165(13) -0.0033(11) O7 0.0610(17) 0.0658(18) 0.0523(16) 0.0142(13) -0.0143(14) -0.0277(14) N1 0.0336(14) 0.0444(16) 0.0443(16) 0.0085(13) -0.0123(12) -0.0080(13) N3 0.0318(13) 0.0320(14) 0.0418(15) 0.0025(11) -0.0104(12) -0.0045(11) C2 0.0359(17) 0.0333(17) 0.0448(19) -0.0002(15) -0.0108(15) -0.0054(14) C4 0.047(2) 0.0355(18) 0.054(2) -0.0080(17) -0.0133(18) -0.0035(16) C5 0.043(2) 0.036(2) 0.071(3) 0.0109(18) -0.0212(19) -0.0133(17) C6 0.059(3) 0.075(3) 0.050(2) 0.016(2) 0.000(2) -0.016(3) C7 0.042(2) 0.046(2) 0.045(2) 0.0009(17) -0.0044(17) -0.0107(18) C8 0.134(6) 0.082(4) 0.075(4) -0.038(3) 0.014(4) -0.024(4) C9 0.054(2) 0.067(3) 0.068(3) -0.036(2) -0.004(2) -0.008(2) C10 0.046(2) 0.035(2) 0.111(4) -0.029(2) -0.004(2) -0.0014(18) C11 0.060(3) 0.037(2) 0.108(4) 0.017(2) -0.034(3) -0.007(2) C12 0.071(3) 0.053(2) 0.087(3) 0.038(2) -0.041(3) -0.027(2) C13 0.062(3) 0.094(4) 0.043(2) 0.018(2) -0.017(2) -0.032(3) C14 0.059(3) 0.113(4) 0.0276(19) -0.010(2) -0.0084(18) -0.019(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 1.396(4) . ? S1 O2 1.407(4) . ? S1 O3 1.435(4) . ? S1 O4 1.574(3) . ? O4 C8 1.469(7) . ? O5 C9 1.413(5) . ? O5 C14 1.434(5) . ? O6 C11 1.409(5) . ? O6 C10 1.426(5) . ? O7 C13 1.396(6) 2_756 ? O7 C12 1.422(5) . ? N1 C2 1.331(4) . ? N1 C5 1.374(5) . ? N1 C6 1.467(5) . ? N3 C2 1.320(4) . ? N3 C4 1.372(4) . ? N3 C7 1.469(5) . ? C2 H2 0.84(4) . ? C4 C5 1.338(6) . ? C4 H4 0.87(4) . ? C5 H5 0.85(5) . ? C6 H61 0.87(6) . ? C6 H62 0.95(6) . ? C6 H63 0.98(7) . ? C7 H71 0.82(7) . ? C7 H72 0.92(6) . ? C7 H73 0.93(7) . ? C8 H81 1.01(4) . ? C8 H82 1.081(7) . ? C8 H83 1.00(6) . ? C9 C10 1.478(7) . ? C9 H91 1.01(5) . ? C9 H92 1.06(6) . ? C10 H101 0.90(5) . ? C10 H102 0.95(5) . ? C11 C12 1.474(8) . ? C11 H111 1.02(5) . ? C11 H112 1.01(6) . ? C12 H121 0.94(6) . ? C12 H122 1.01(5) . ? C13 O7 1.396(6) 2_756 ? C13 C14 1.478(7) . ? C13 H131 0.97(6) . ? C13 H132 0.96(5) . ? C14 H141 0.87(5) . ? C14 H142 1.00(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 O2 116.2(3) . . ? O1 S1 O3 111.3(3) . . ? O2 S1 O3 110.1(3) . . ? O1 S1 O4 107.3(2) . . ? O2 S1 O4 110.5(3) . . ? O3 S1 O4 100.2(2) . . ? C8 O4 S1 114.0(4) . . ? C9 O5 C14 112.2(3) . . ? C11 O6 C10 111.7(3) . . ? C13 O7 C12 113.0(4) 2_756 . ? C2 N1 C5 108.2(3) . . ? C2 N1 C6 125.1(4) . . ? C5 N1 C6 126.6(4) . . ? C2 N3 C4 108.4(3) . . ? C2 N3 C7 125.7(3) . . ? C4 N3 C7 125.8(3) . . ? N3 C2 N1 108.7(3) . . ? N3 C2 H2 127(3) . . ? N1 C2 H2 125(3) . . ? C5 C4 N3 107.5(3) . . ? C5 C4 H4 131(2) . . ? N3 C4 H4 121(3) . . ? C4 C5 N1 107.1(3) . . ? C4 C5 H5 129(3) . . ? N1 C5 H5 124(3) . . ? N1 C6 H61 107(4) . . ? N1 C6 H62 111(3) . . ? H61 C6 H62 107(5) . . ? N1 C6 H63 110(4) . . ? H61 C6 H63 113(5) . . ? H62 C6 H63 108(5) . . ? N3 C7 H71 110(4) . . ? N3 C7 H72 111(3) . . ? H71 C7 H72 113(5) . . ? N3 C7 H73 110(4) . . ? H71 C7 H73 107(5) . . ? H72 C7 H73 105(5) . . ? O4 C8 H81 114(2) . . ? O4 C8 H82 119.1(5) . . ? H81 C8 H82 80(2) . . ? O4 C8 H83 104(4) . . ? H81 C8 H83 131(4) . . ? H82 C8 H83 107(4) . . ? O5 C9 C10 109.4(3) . . ? O5 C9 H91 109(3) . . ? C10 C9 H91 110(3) . . ? O5 C9 H92 109(3) . . ? C10 C9 H92 105(3) . . ? H91 C9 H92 113(4) . . ? O6 C10 C9 111.0(3) . . ? O6 C10 H101 113(3) . . ? C9 C10 H101 108(3) . . ? O6 C10 H102 114(3) . . ? C9 C10 H102 109(3) . . ? H101 C10 H102 102(4) . . ? O6 C11 C12 109.8(3) . . ? O6 C11 H111 111(3) . . ? C12 C11 H111 106(3) . . ? O6 C11 H112 110(3) . . ? C12 C11 H112 108(3) . . ? H111 C11 H112 112(4) . . ? O7 C12 C11 111.0(4) . . ? O7 C12 H121 111(3) . . ? C11 C12 H121 113(3) . . ? O7 C12 H122 106(3) . . ? C11 C12 H122 115(3) . . ? H121 C12 H122 100(4) . . ? O7 C13 C14 109.7(4) 2_756 . ? O7 C13 H131 114(3) 2_756 . ? C14 C13 H131 108(3) . . ? O7 C13 H132 110(3) 2_756 . ? C14 C13 H132 113(3) . . ? H131 C13 H132 103(4) . . ? O5 C14 C13 110.5(3) . . ? O5 C14 H141 111(3) . . ? C13 C14 H141 109(3) . . ? O5 C14 H142 110(3) . . ? C13 C14 H142 113(3) . . ? H141 C14 H142 103(4) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.573 _refine_diff_density_min -0.321 _refine_diff_density_rms 0.061 data_2 _database_code_depnum_ccdc_archive 'CCDC 648113' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '1-butyl-3-methylimidazolium methylsulfate (18-crown-6)' _chemical_melting_point ? _chemical_formula_moiety 'C30 H60 N4 O14 S2' _chemical_formula_sum 'C30 H60 N4 O14 S2' _chemical_formula_weight 764.94 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 P21/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 9.1227(11) _cell_length_b 16.1877(14) _cell_length_c 13.9387(16) _cell_angle_alpha 90.00 _cell_angle_beta 98.028(10) _cell_angle_gamma 90.00 _cell_volume 2038.2(4) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.94 _cell_measurement_theta_max 25.02 _exptl_crystal_description cubic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.246 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.194 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 'IPDS II (Stoe & Cie)' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean 'not measured' _diffrn_standards_number 'not measured' _diffrn_standards_interval_count 'not measured' _diffrn_standards_interval_time 'not measured' _diffrn_standards_decay_% 'not measured' _diffrn_reflns_number 21359 _diffrn_reflns_av_R_equivalents 0.0747 _diffrn_reflns_av_sigmaI/netI 0.0361 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3598 _reflns_number_gt 2898 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0681P)^2^+1.4560P] 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 0.015(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3598 _refine_ls_number_parameters 336 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0779 _refine_ls_R_factor_gt 0.0612 _refine_ls_wR_factor_ref 0.1591 _refine_ls_wR_factor_gt 0.1484 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _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 S S 0.70554(8) 0.22306(5) 0.15473(6) 0.0506(3) Uani 1 1 d . . . O1 O 0.6057(3) 0.27714(19) 0.1010(2) 0.0879(9) Uani 1 1 d . . . O2 O 0.8491(3) 0.2277(2) 0.1303(3) 0.1020(11) Uani 1 1 d . . . O3 O 0.7028(6) 0.2279(3) 0.2572(2) 0.1327(15) Uani 1 1 d . . . O4 O 0.6437(4) 0.1336(2) 0.1350(3) 0.1096(12) Uani 1 1 d . . . O5 O 0.1910(2) 0.41306(13) 0.14700(14) 0.0478(5) Uani 1 1 d . . . O6 O -0.0760(2) 0.48625(12) 0.19071(15) 0.0462(5) Uani 1 1 d . . . O7 O 0.2933(2) 0.47079(12) -0.02743(15) 0.0447(5) Uani 1 1 d . . . N1 N 0.3419(2) 0.14731(14) 0.38837(16) 0.0380(5) Uani 1 1 d . . . N3 N 0.2524(3) 0.18314(15) 0.24348(17) 0.0449(6) Uani 1 1 d . . . C2 C 0.3728(3) 0.15673(17) 0.2995(2) 0.0420(6) Uani 1 1 d . . . C4 C 0.1406(3) 0.1908(2) 0.2988(2) 0.0523(8) Uani 1 1 d . . . C5 C 0.1969(3) 0.16920(19) 0.3897(2) 0.0483(7) Uani 1 1 d . . . C6 C 0.4438(4) 0.1179(2) 0.4720(2) 0.0495(7) Uani 1 1 d . . . C7 C 0.2408(5) 0.2009(2) 0.1387(2) 0.0612(9) Uani 1 1 d . . . C8 C 0.1697(6) 0.1341(3) 0.0782(3) 0.0748(11) Uani 1 1 d . . . C9 C 0.1555(8) 0.1587(4) -0.0294(3) 0.1084(18) Uani 1 1 d . . . C10 C 0.0659(8) 0.1015(6) -0.0932(5) 0.169(4) Uani 1 1 d . . . H10A H 0.1184 0.0503 -0.0960 0.253 Uiso 1 1 calc R . . H10B H 0.0459 0.1249 -0.1570 0.253 Uiso 1 1 calc R . . H10C H -0.0258 0.0915 -0.0687 0.253 Uiso 1 1 calc R . . C11 C 0.6367(11) 0.1068(7) 0.0340(7) 0.136(3) Uani 1 1 d . . . C12 C 0.1610(4) 0.4285(2) 0.2421(2) 0.0537(8) Uani 1 1 d . . . C13 C -0.0016(4) 0.4205(2) 0.2446(2) 0.0547(8) Uani 1 1 d . . . C14 C -0.2317(3) 0.4816(2) 0.1894(2) 0.0516(8) Uani 1 1 d . . . C15 C -0.3043(3) 0.5478(2) 0.1253(2) 0.0497(7) Uani 1 1 d . . . C16 C 0.3665(3) 0.4106(2) 0.0360(3) 0.0507(8) Uani 1 1 d . . . C17 C 0.3417(3) 0.4274(2) 0.1373(3) 0.0520(8) Uani 1 1 d . . . H2 H 0.462(4) 0.148(2) 0.276(2) 0.060(10) Uiso 1 1 d . . . H4 H 0.045(4) 0.205(2) 0.272(3) 0.063(10) Uiso 1 1 d . . . H5 H 0.160(4) 0.168(2) 0.448(3) 0.055(9) Uiso 1 1 d . . . H61 H 0.407(4) 0.066(3) 0.497(3) 0.076(11) Uiso 1 1 d . . . H62 H 0.530(5) 0.108(3) 0.456(3) 0.088(14) Uiso 1 1 d . . . H63 H 0.454(5) 0.158(3) 0.519(3) 0.092(14) Uiso 1 1 d . . . H71 H 0.337(5) 0.218(3) 0.128(3) 0.088(14) Uiso 1 1 d . . . H72 H 0.175(5) 0.245(3) 0.132(3) 0.082(13) Uiso 1 1 d . . . H81 H 0.085(5) 0.111(3) 0.103(3) 0.092(15) Uiso 1 1 d . . . H82 H 0.243(4) 0.092(2) 0.085(3) 0.062(10) Uiso 1 1 d . . . H91 H 0.251(5) 0.143(3) -0.051(3) 0.091(15) Uiso 1 1 d . . . H92 H 0.037(6) 0.184(3) -0.057(4) 0.121(18) Uiso 1 1 d . . . H111 H 0.611(11) 0.143(6) -0.005(7) 0.21(5) Uiso 1 1 d . . . H112 H 0.615(8) 0.058(5) 0.034(6) 0.16(3) Uiso 1 1 d . . . H113 H 0.749(5) 0.139(3) 0.056(3) 0.077(12) Uiso 1 1 d . . . H121 H 0.216(4) 0.389(2) 0.283(3) 0.061(10) Uiso 1 1 d . . . H122 H 0.199(3) 0.483(2) 0.261(2) 0.053(9) Uiso 1 1 d . . . H131 H -0.017(4) 0.422(2) 0.311(3) 0.062(10) Uiso 1 1 d . . . H132 H -0.036(3) 0.362(2) 0.215(2) 0.053(9) Uiso 1 1 d . . . H141 H -0.265(3) 0.427(2) 0.168(2) 0.049(8) Uiso 1 1 d . . . H142 H -0.256(4) 0.492(2) 0.255(3) 0.063(10) Uiso 1 1 d . . . H151 H 0.412(4) 0.449(2) -0.135(2) 0.057(9) Uiso 1 1 d . . . H152 H 0.264(3) 0.398(2) -0.141(2) 0.043(8) Uiso 1 1 d . . . H161 H 0.333(3) 0.357(2) 0.015(2) 0.046(8) Uiso 1 1 d . . . H162 H 0.473(4) 0.410(2) 0.033(2) 0.058(9) Uiso 1 1 d . . . H171 H 0.409(3) 0.3933(18) 0.180(2) 0.042(8) Uiso 1 1 d . . . H172 H 0.369(4) 0.484(2) 0.152(3) 0.063(10) 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 S 0.0471(4) 0.0487(5) 0.0551(5) 0.0190(4) 0.0043(3) 0.0017(3) O1 0.0877(19) 0.0825(19) 0.089(2) 0.0218(16) -0.0033(15) 0.0324(15) O2 0.0507(15) 0.110(2) 0.145(3) 0.002(2) 0.0136(16) -0.0022(15) O3 0.214(5) 0.126(3) 0.0611(19) 0.021(2) 0.028(2) -0.010(3) O4 0.133(3) 0.0670(19) 0.127(3) 0.0183(19) 0.011(2) -0.0280(19) O5 0.0400(10) 0.0550(12) 0.0463(11) -0.0046(9) -0.0014(8) -0.0029(9) O6 0.0437(11) 0.0480(11) 0.0472(11) 0.0010(9) 0.0080(9) -0.0022(9) O7 0.0382(10) 0.0436(11) 0.0528(12) -0.0020(9) 0.0075(8) 0.0064(8) N1 0.0380(12) 0.0376(12) 0.0378(12) 0.0011(9) 0.0032(9) -0.0005(9) N3 0.0484(13) 0.0431(13) 0.0422(13) 0.0076(10) 0.0032(10) 0.0036(11) C2 0.0426(15) 0.0423(15) 0.0414(15) 0.0035(12) 0.0067(12) 0.0028(12) C4 0.0398(16) 0.0548(19) 0.061(2) 0.0088(15) 0.0006(14) 0.0060(13) C5 0.0435(16) 0.0521(17) 0.0507(18) -0.0007(14) 0.0111(14) 0.0002(13) C6 0.0471(18) 0.057(2) 0.0420(17) 0.0046(15) -0.0021(14) 0.0017(15) C7 0.078(3) 0.061(2) 0.0427(18) 0.0147(15) 0.0016(17) 0.0054(19) C8 0.090(3) 0.084(3) 0.049(2) 0.0025(19) 0.001(2) 0.004(3) C9 0.127(5) 0.137(5) 0.054(3) -0.002(3) -0.014(3) 0.015(4) C10 0.145(6) 0.277(11) 0.080(4) -0.045(5) 0.000(4) -0.009(7) C11 0.171(8) 0.108(6) 0.122(6) -0.052(5) -0.007(5) -0.023(5) C12 0.0578(19) 0.060(2) 0.0394(16) 0.0014(15) -0.0067(14) 0.0033(16) C13 0.064(2) 0.063(2) 0.0369(16) 0.0085(15) 0.0064(14) 0.0007(16) C14 0.0470(17) 0.061(2) 0.0495(18) -0.0050(15) 0.0171(14) -0.0087(15) C15 0.0388(15) 0.0523(18) 0.061(2) -0.0117(15) 0.0162(14) -0.0005(13) C16 0.0348(15) 0.0467(18) 0.069(2) 0.0014(15) 0.0036(14) 0.0092(13) C17 0.0380(15) 0.0527(19) 0.061(2) 0.0027(16) -0.0079(14) 0.0016(14) _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 S O2 1.400(3) . ? S O1 1.402(3) . ? S O3 1.434(3) . ? S O4 1.565(3) . ? O4 C11 1.465(9) . ? O5 C12 1.413(4) . ? O5 C17 1.419(4) . ? O6 C14 1.419(4) . ? O6 C13 1.420(4) . ? O7 C15 1.414(4) 3_565 ? O7 C16 1.418(4) . ? N1 C2 1.317(4) . ? N1 C5 1.373(4) . ? N1 C6 1.465(4) . ? N3 C2 1.327(4) . ? N3 C4 1.367(4) . ? N3 C7 1.477(4) . ? C2 H2 0.93(4) . ? C4 C5 1.345(5) . ? C4 H4 0.93(4) . ? C5 H5 0.92(4) . ? C6 H61 0.98(4) . ? C6 H62 0.86(5) . ? C6 H63 0.91(5) . ? C7 C8 1.466(6) . ? C7 H71 0.95(4) . ? C7 H72 0.93(4) . ? C8 C9 1.539(6) . ? C8 H81 0.96(5) . ? C8 H82 0.95(4) . ? C9 C10 1.454(9) . ? C9 H91 1.00(5) . ? C9 H92 1.17(6) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C10 H92 1.47(6) . ? C11 H111 0.81(9) . ? C11 H112 0.81(8) . ? C11 H113 1.15(4) . ? C12 C13 1.494(5) . ? C12 H121 0.96(4) . ? C12 H122 0.98(3) . ? C13 H131 0.96(4) . ? C13 H132 1.07(3) . ? C14 C15 1.490(5) . ? C14 H141 0.97(3) . ? C14 H142 0.98(4) . ? C15 O7 1.414(4) 3_565 ? C16 C17 1.486(5) . ? C16 H161 0.94(3) . ? C16 H162 0.98(3) . ? C17 H171 0.96(3) . ? C17 H172 0.97(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 O2 S O1 113.4(2) . . ? O2 S O3 112.7(3) . . ? O1 S O3 113.4(2) . . ? O2 S O4 109.4(2) . . ? O1 S O4 107.0(2) . . ? O3 S O4 99.8(2) . . ? C11 O4 S 114.2(5) . . ? C12 O5 C17 112.2(2) . . ? C14 O6 C13 111.8(2) . . ? C15 O7 C16 111.4(2) 3_565 . ? C2 N1 C5 108.4(2) . . ? C2 N1 C6 126.2(3) . . ? C5 N1 C6 125.3(3) . . ? C2 N3 C4 108.6(3) . . ? C2 N3 C7 125.7(3) . . ? C4 N3 C7 125.7(3) . . ? N1 C2 N3 108.8(3) . . ? N1 C2 H2 129(2) . . ? N3 C2 H2 123(2) . . ? C5 C4 N3 106.9(3) . . ? C5 C4 H4 131(2) . . ? N3 C4 H4 122(2) . . ? C4 C5 N1 107.2(3) . . ? C4 C5 H5 134(2) . . ? N1 C5 H5 119(2) . . ? N1 C6 H61 110(2) . . ? N1 C6 H62 111(3) . . ? H61 C6 H62 107(4) . . ? N1 C6 H63 109(3) . . ? H61 C6 H63 111(4) . . ? H62 C6 H63 108(4) . . ? C8 C7 N3 113.0(3) . . ? C8 C7 H71 118(3) . . ? N3 C7 H71 106(3) . . ? C8 C7 H72 106(3) . . ? N3 C7 H72 102(3) . . ? H71 C7 H72 110(4) . . ? C7 C8 C9 109.9(4) . . ? C7 C8 H81 113(3) . . ? C9 C8 H81 119(3) . . ? C7 C8 H82 103(2) . . ? C9 C8 H82 104(2) . . ? H81 C8 H82 107(4) . . ? C10 C9 C8 113.2(6) . . ? C10 C9 H91 95(3) . . ? C8 C9 H91 106(3) . . ? C10 C9 H92 67(3) . . ? C8 C9 H92 111(3) . . ? H91 C9 H92 143(4) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C10 H92 47(2) . . ? H10A C10 H92 156.2 . . ? H10B C10 H92 86.7 . . ? H10C C10 H92 79.8 . . ? O4 C11 H111 114(7) . . ? O4 C11 H112 105(6) . . ? H111 C11 H112 131(8) . . ? O4 C11 H113 72(2) . . ? H111 C11 H113 91(7) . . ? H112 C11 H113 130(6) . . ? O5 C12 C13 109.3(2) . . ? O5 C12 H121 107(2) . . ? C13 C12 H121 112(2) . . ? O5 C12 H122 107.7(19) . . ? C13 C12 H122 113.0(19) . . ? H121 C12 H122 108(3) . . ? O6 C13 C12 109.0(3) . . ? O6 C13 H131 112(2) . . ? C12 C13 H131 108(2) . . ? O6 C13 H132 111.7(17) . . ? C12 C13 H132 107.7(17) . . ? H131 C13 H132 109(3) . . ? O6 C14 C15 109.3(3) . . ? O6 C14 H141 108.9(18) . . ? C15 C14 H141 111.9(19) . . ? O6 C14 H142 109(2) . . ? C15 C14 H142 107(2) . . ? H141 C14 H142 110(3) . . ? O7 C15 C14 109.9(2) 3_565 . ? O7 C16 C17 110.3(3) . . ? O7 C16 H161 109.3(19) . . ? C17 C16 H161 112.0(19) . . ? O7 C16 H162 111(2) . . ? C17 C16 H162 109.2(19) . . ? H161 C16 H162 105(3) . . ? O5 C17 C16 109.8(3) . . ? O5 C17 H171 112.9(17) . . ? C16 C17 H171 108.1(17) . . ? O5 C17 H172 111(2) . . ? C16 C17 H172 108(2) . . ? H171 C17 H172 107(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.427 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.045 data_4 _database_code_depnum_ccdc_archive 'CCDC 648114' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ;1-ethyl-3-methylimidazolium trifluoromethanesulfonate (18- crown-6) ; _chemical_melting_point ? _chemical_formula_moiety 'C26 H46 F6 N4 O12 S2' _chemical_formula_sum 'C26 H46 F6 N4 O12 S2' _chemical_formula_weight 784.79 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.946(2) _cell_length_b 9.165(2) _cell_length_c 11.469(3) _cell_angle_alpha 92.604(18) _cell_angle_beta 98.722(18) _cell_angle_gamma 97.862(19) _cell_volume 918.6(4) _cell_formula_units_Z 1 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 16326 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 25.02 _exptl_crystal_description cubic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.419 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 412 _exptl_absorpt_coefficient_mu 0.236 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 'IPDS II (Stoe & Cie)' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean 'not measured' _diffrn_standards_number 'not measured' _diffrn_standards_interval_count 'not measured' _diffrn_standards_interval_time 'not measured' _diffrn_standards_decay_% 'not measured' _diffrn_reflns_number 9846 _diffrn_reflns_av_R_equivalents 0.0578 _diffrn_reflns_av_sigmaI/netI 0.0542 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3202 _reflns_number_gt 2141 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0316P)^2^+0.7699P] 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 0.0028(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3202 _refine_ls_number_parameters 319 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1016 _refine_ls_R_factor_gt 0.0612 _refine_ls_wR_factor_ref 0.1217 _refine_ls_wR_factor_gt 0.1080 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.009 _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 S S 0.39850(12) 0.16950(11) 0.19392(9) 0.0485(3) Uani 1 1 d . . . F1 F 0.3145(5) 0.0208(4) -0.0085(3) 0.1274(14) Uani 1 1 d . . . F2 F 0.1384(4) 0.0233(5) 0.0960(3) 0.1289(16) Uani 1 1 d . . . F3 F 0.2091(3) 0.2092(4) 0.0069(2) 0.0981(11) Uani 1 1 d . . . N1 N 0.5577(3) 0.6440(3) 0.2753(3) 0.0475(8) Uani 1 1 d . . . N2 N 0.6814(3) 0.5934(3) 0.4407(2) 0.0330(6) Uani 1 1 d . . . O1 O 0.4343(5) 0.0411(4) 0.2478(4) 0.1126(15) Uani 1 1 d . . . O2 O 0.5184(4) 0.2517(4) 0.1447(3) 0.0805(10) Uani 1 1 d . . . O3 O 0.3186(4) 0.2607(5) 0.2596(3) 0.0944(12) Uani 1 1 d . . . O4 O 1.0678(3) 0.8070(3) 0.4994(2) 0.0471(6) Uani 1 1 d . . . O5 O 1.0238(3) 0.6255(3) 0.2832(2) 0.0515(7) Uani 1 1 d . . . O6 O 0.8824(3) 0.3333(3) 0.2819(2) 0.0465(6) Uani 1 1 d . . . C2 C 0.6319(4) 0.5446(4) 0.3302(3) 0.0435(9) Uani 1 1 d . . . C4 C 0.6378(4) 0.7293(4) 0.4586(3) 0.0418(9) Uani 1 1 d . . . C5 C 0.5595(4) 0.7600(4) 0.3559(4) 0.0478(10) Uani 1 1 d . . . C6 C 0.4975(6) 0.6348(8) 0.1455(4) 0.0766(15) Uani 1 1 d . . . C7 C 0.3311(7) 0.6299(9) 0.1252(6) 0.100(2) Uani 1 1 d . . . C8 C 0.7776(5) 0.5182(5) 0.5283(4) 0.0478(10) Uani 1 1 d . . . C9 C 0.2586(5) 0.1008(5) 0.0657(4) 0.0584(11) Uani 1 1 d . . . C10 C 1.1146(5) 0.8521(5) 0.3928(4) 0.0574(12) Uani 1 1 d . . . C11 C 1.0088(5) 0.7776(5) 0.2892(4) 0.0555(11) Uani 1 1 d . . . C12 C 0.9411(5) 0.5472(5) 0.1792(3) 0.0578(12) Uani 1 1 d . . . C13 C 0.9510(6) 0.3860(5) 0.1871(3) 0.0554(11) Uani 1 1 d . . . C14 C 0.8844(6) 0.1790(5) 0.2903(4) 0.0631(13) Uani 1 1 d . . . C15 C 0.8269(5) 0.1317(5) 0.4003(4) 0.0587(12) Uani 1 1 d . . . H2 H 0.647(4) 0.456(4) 0.297(3) 0.037(9) Uiso 1 1 d . . . H4 H 0.664(4) 0.782(4) 0.528(3) 0.041(10) Uiso 1 1 d . . . H5 H 0.517(4) 0.834(4) 0.339(3) 0.049(11) Uiso 1 1 d . . . H61 H 0.516(6) 0.728(6) 0.104(5) 0.094(17) Uiso 1 1 d . . . H62 H 0.531(9) 0.563(9) 0.090(6) 0.18(3) Uiso 1 1 d . . . H71 H 0.303(6) 0.631(6) 0.033(5) 0.103(17) Uiso 1 1 d . . . H72 H 0.304(15) 0.733(15) 0.174(11) 0.34(7) Uiso 1 1 d . . . H73 H 0.384(6) 0.591(5) 0.185(4) 0.066(13) Uiso 1 1 d . . . H81 H 0.714(6) 0.492(6) 0.593(5) 0.095(17) Uiso 1 1 d . . . H82 H 0.869(6) 0.581(5) 0.555(4) 0.073(14) Uiso 1 1 d . . . H83 H 0.792(6) 0.430(6) 0.491(4) 0.096(18) Uiso 1 1 d . . . H101 H 1.216(4) 0.832(4) 0.391(3) 0.048(10) Uiso 1 1 d . . . H102 H 1.119(4) 0.952(5) 0.393(3) 0.058(11) Uiso 1 1 d . . . H111 H 1.032(5) 0.822(4) 0.216(4) 0.063(12) Uiso 1 1 d . . . H112 H 0.901(5) 0.790(5) 0.291(4) 0.070(13) Uiso 1 1 d . . . H121 H 0.983(4) 0.587(4) 0.110(3) 0.049(10) Uiso 1 1 d . . . H122 H 0.837(4) 0.560(4) 0.168(3) 0.047(10) Uiso 1 1 d . . . H131 H 1.056(5) 0.374(4) 0.198(3) 0.056(11) Uiso 1 1 d . . . H132 H 0.899(5) 0.330(5) 0.111(4) 0.069(13) Uiso 1 1 d . . . H141 H 0.817(5) 0.125(5) 0.222(4) 0.082(15) Uiso 1 1 d . . . H142 H 0.989(5) 0.160(4) 0.295(3) 0.063(12) Uiso 1 1 d . . . H41 H 0.722(5) 0.162(4) 0.406(3) 0.063(12) Uiso 1 1 d . . . H42 H 0.806(5) 0.025(5) 0.401(4) 0.072(13) 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 S 0.0510(6) 0.0510(6) 0.0425(5) 0.0014(4) -0.0059(4) 0.0195(5) F1 0.129(3) 0.141(3) 0.097(2) -0.074(2) -0.008(2) 0.020(2) F2 0.087(2) 0.165(4) 0.106(2) 0.050(2) -0.0178(19) -0.063(2) F3 0.087(2) 0.130(3) 0.0714(18) 0.0463(19) -0.0193(15) 0.0174(19) N1 0.0477(19) 0.0513(19) 0.0409(17) 0.0042(15) -0.0062(14) 0.0126(15) N2 0.0314(15) 0.0305(14) 0.0363(16) 0.0031(12) 0.0002(12) 0.0076(12) O1 0.134(4) 0.075(2) 0.115(3) 0.036(2) -0.046(3) 0.030(2) O2 0.0548(19) 0.087(2) 0.090(2) -0.0098(19) 0.0040(17) -0.0129(17) O3 0.094(3) 0.140(3) 0.0575(19) -0.023(2) 0.0109(18) 0.056(2) O4 0.0402(14) 0.0376(13) 0.0625(17) 0.0050(13) 0.0063(13) 0.0032(11) O5 0.0595(17) 0.0528(16) 0.0473(15) 0.0164(13) 0.0036(13) 0.0269(13) O6 0.0464(15) 0.0485(15) 0.0452(14) -0.0053(12) 0.0008(12) 0.0186(12) C2 0.046(2) 0.037(2) 0.046(2) -0.0009(18) -0.0011(17) 0.0120(17) C4 0.047(2) 0.0338(19) 0.043(2) -0.0013(17) 0.0022(18) 0.0075(16) C5 0.043(2) 0.039(2) 0.063(3) 0.0109(19) 0.0017(19) 0.0181(18) C6 0.069(3) 0.118(5) 0.042(3) 0.010(3) 0.001(2) 0.020(3) C7 0.067(4) 0.156(6) 0.069(4) 0.009(4) -0.024(3) 0.031(4) C8 0.047(2) 0.045(2) 0.049(2) 0.010(2) -0.006(2) 0.014(2) C9 0.055(3) 0.064(3) 0.051(3) 0.007(2) 0.001(2) -0.004(2) C10 0.047(2) 0.036(2) 0.095(4) 0.029(2) 0.020(2) 0.0091(19) C11 0.056(3) 0.053(3) 0.066(3) 0.034(2) 0.014(2) 0.022(2) C12 0.056(3) 0.089(3) 0.036(2) 0.019(2) 0.006(2) 0.034(3) C13 0.058(3) 0.077(3) 0.033(2) -0.006(2) -0.002(2) 0.031(2) C14 0.064(3) 0.044(2) 0.074(3) -0.023(2) -0.013(3) 0.017(2) C15 0.051(3) 0.034(2) 0.086(3) -0.005(2) 0.003(2) 0.0001(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 S O1 1.406(3) . ? S O2 1.428(3) . ? S O3 1.430(3) . ? S C9 1.808(4) . ? F1 C9 1.298(5) . ? F2 C9 1.307(5) . ? F3 C9 1.314(5) . ? N1 C2 1.326(4) . ? N1 C5 1.373(5) . ? N1 C6 1.499(5) . ? N2 C2 1.315(4) . ? N2 C4 1.370(4) . ? N2 C8 1.479(4) . ? O4 C10 1.412(5) . ? O4 C15 1.412(5) 2_766 ? O5 C12 1.413(5) . ? O5 C11 1.418(5) . ? O6 C13 1.400(5) . ? O6 C14 1.424(5) . ? C2 H2 0.91(3) . ? C4 C5 1.338(5) . ? C4 H4 0.90(4) . ? C5 H5 0.83(4) . ? C6 C7 1.465(8) . ? C6 H61 1.01(5) . ? C6 H62 1.00(8) . ? C6 H73 1.20(5) . ? C7 H71 1.05(5) . ? C7 H72 1.15(14) . ? C7 H73 0.89(5) . ? C8 H81 1.02(5) . ? C8 H82 0.93(5) . ? C8 H83 0.93(6) . ? C10 C11 1.477(6) . ? C10 H101 0.95(4) . ? C10 H102 0.91(4) . ? C11 H111 0.99(4) . ? C11 H112 0.99(5) . ? C12 C13 1.498(6) . ? C12 H121 0.99(4) . ? C12 H122 0.95(4) . ? C13 H131 0.95(4) . ? C13 H132 1.00(4) . ? C14 C15 1.493(7) . ? C14 H141 0.98(5) . ? C14 H142 0.97(4) . ? C15 O4 1.412(5) 2_766 ? C15 H41 1.02(4) . ? C15 H42 0.97(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 S O2 115.9(3) . . ? O1 S O3 115.0(3) . . ? O2 S O3 113.1(2) . . ? O1 S C9 104.0(2) . . ? O2 S C9 103.43(19) . . ? O3 S C9 103.4(2) . . ? C2 N1 C5 107.8(3) . . ? C2 N1 C6 124.8(4) . . ? C5 N1 C6 127.1(4) . . ? C2 N2 C4 108.7(3) . . ? C2 N2 C8 125.2(3) . . ? C4 N2 C8 125.9(3) . . ? C10 O4 C15 112.2(3) . 2_766 ? C12 O5 C11 113.3(3) . . ? C13 O6 C14 111.7(3) . . ? N2 C2 N1 109.0(3) . . ? N2 C2 H2 125(2) . . ? N1 C2 H2 126(2) . . ? C5 C4 N2 106.9(3) . . ? C5 C4 H4 131(2) . . ? N2 C4 H4 122(2) . . ? C4 C5 N1 107.5(3) . . ? C4 C5 H5 130(3) . . ? N1 C5 H5 123(3) . . ? C7 C6 N1 110.6(5) . . ? C7 C6 H61 94(3) . . ? N1 C6 H61 116(3) . . ? C7 C6 H62 112(5) . . ? N1 C6 H62 121(4) . . ? H61 C6 H62 100(5) . . ? C7 C6 H73 38(2) . . ? N1 C6 H73 78(2) . . ? H61 C6 H73 126(4) . . ? H62 C6 H73 116(5) . . ? C6 C7 H71 104(3) . . ? C6 C7 H72 108(7) . . ? H71 C7 H72 113(7) . . ? C6 C7 H73 55(3) . . ? H71 C7 H73 146(4) . . ? H72 C7 H73 100(6) . . ? N2 C8 H81 106(3) . . ? N2 C8 H82 109(3) . . ? H81 C8 H82 114(4) . . ? N2 C8 H83 107(3) . . ? H81 C8 H83 107(4) . . ? H82 C8 H83 113(4) . . ? F1 C9 F2 109.0(4) . . ? F1 C9 F3 106.3(4) . . ? F2 C9 F3 106.4(4) . . ? F1 C9 S 112.0(3) . . ? F2 C9 S 111.3(3) . . ? F3 C9 S 111.5(3) . . ? O4 C10 C11 111.1(3) . . ? O4 C10 H101 110(2) . . ? C11 C10 H101 111(2) . . ? O4 C10 H102 108(3) . . ? C11 C10 H102 111(2) . . ? H101 C10 H102 106(3) . . ? O5 C11 C10 108.8(3) . . ? O5 C11 H111 110(2) . . ? C10 C11 H111 111(2) . . ? O5 C11 H112 110(2) . . ? C10 C11 H112 113(3) . . ? H111 C11 H112 104(3) . . ? O5 C12 C13 109.2(3) . . ? O5 C12 H121 109(2) . . ? C13 C12 H121 112(2) . . ? O5 C12 H122 112(2) . . ? C13 C12 H122 109(2) . . ? H121 C12 H122 107(3) . . ? O6 C13 C12 109.8(3) . . ? O6 C13 H131 111(2) . . ? C12 C13 H131 108(2) . . ? O6 C13 H132 110(2) . . ? C12 C13 H132 110(2) . . ? H131 C13 H132 108(3) . . ? O6 C14 C15 109.6(4) . . ? O6 C14 H141 109(3) . . ? C15 C14 H141 108(3) . . ? O6 C14 H142 109(2) . . ? C15 C14 H142 108(2) . . ? H141 C14 H142 113(4) . . ? O4 C15 C14 109.9(4) 2_766 . ? O4 C15 H41 110(2) 2_766 . ? C14 C15 H41 112(2) . . ? O4 C15 H42 111(3) 2_766 . ? C14 C15 H42 112(3) . . ? H41 C15 H42 102(3) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.263 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.044 data_3 _database_code_depnum_ccdc_archive 'CCDC 648115' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '1-ethyl-3-methylimidazolium methanesulfanate (18-crown-6)' _chemical_melting_point ? _chemical_formula_moiety 'C12 H24 O6, (C6 H11 N2)2 (SO3 CH3)2' _chemical_formula_sum 'C26 H52 N4 O12 S2' _chemical_formula_weight 676.84 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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.751(5) _cell_length_b 9.126(4) _cell_length_c 11.357(6) _cell_angle_alpha 97.26(4) _cell_angle_beta 97.99(4) _cell_angle_gamma 97.76(4) _cell_volume 880.1(7) _cell_formula_units_Z 1 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 11401 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 25.02 _exptl_crystal_description cubic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 364 _exptl_absorpt_coefficient_mu 0.212 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 'IPDS II (Stoe & Cie)' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean 'not measured' _diffrn_standards_number 'not measured' _diffrn_standards_interval_count 'not measured' _diffrn_standards_interval_time 'not measured' _diffrn_standards_decay_% 'not measured' _diffrn_reflns_number 11401 _diffrn_reflns_av_R_equivalents 0.1755 _diffrn_reflns_av_sigmaI/netI 0.1189 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 25.03 _reflns_number_total 3085 _reflns_number_gt 1860 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0519P)^2^+0.4026P] 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 3085 _refine_ls_number_parameters 303 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1172 _refine_ls_R_factor_gt 0.0725 _refine_ls_wR_factor_ref 0.1638 _refine_ls_wR_factor_gt 0.1454 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.016 _refine_ls_shift/su_mean 0.001 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 S S 0.37461(14) 0.12605(14) 0.69039(11) 0.0486(4) Uani 1 1 d . . . O1 O 0.2872(5) 0.2331(5) 0.7406(4) 0.0954(15) Uani 1 1 d . . . O2 O 0.3923(6) 0.0085(5) 0.7611(4) 0.0990(16) Uani 1 1 d . . . O3 O 0.5198(5) 0.2007(5) 0.6652(4) 0.0856(13) Uani 1 1 d . . . O4 O 0.9332(4) 0.1909(3) 1.9894(3) 0.0502(8) Uani 1 1 d . . . O5 O 0.8826(4) 0.3322(3) 1.7777(3) 0.0537(9) Uani 1 1 d . . . O6 O 1.0310(4) 0.6293(4) 1.7783(3) 0.0553(9) Uani 1 1 d . . . N1 N 0.4854(5) 0.3793(5) 1.2030(3) 0.0542(10) Uani 1 1 d . . . N3 N 0.3264(4) 0.4119(4) 1.0509(3) 0.0416(9) Uani 1 1 d . . . C2 C 0.4039(5) 0.4768(6) 1.1567(4) 0.0496(12) Uani 1 1 d . . . C4 C 0.4578(6) 0.2489(6) 1.1247(5) 0.0515(12) Uani 1 1 d . . . C5 C 0.3603(5) 0.2691(5) 1.0297(5) 0.0462(11) Uani 1 1 d . . . C6 C 0.5921(9) 0.4079(9) 1.3175(6) 0.0793(19) Uani 1 1 d . . . C7 C 0.5209(12) 0.3215(10) 1.4051(7) 0.093(2) Uani 1 1 d . . . C8 C 0.2184(7) 0.4797(7) 0.9710(5) 0.0513(12) Uani 1 1 d . . . C9 C 0.2682(9) 0.0435(9) 0.5506(6) 0.0773(19) Uani 1 1 d . . . C10 C 0.8224(6) 0.1292(6) 1.8850(5) 0.0594(14) Uani 1 1 d . . . C11 C 0.8809(7) 0.1753(5) 1.7771(5) 0.0574(13) Uani 1 1 d . . . C12 C 0.9417(7) 0.3821(7) 1.6765(5) 0.0628(15) Uani 1 1 d . . . C13 C 0.9301(8) 0.5441(7) 1.6778(5) 0.0636(15) Uani 1 1 d . . . C14 C 0.9916(7) 0.2195(6) 2.2021(6) 0.0607(14) Uani 1 1 d . . . C15 C 0.8849(7) 0.1389(6) 2.0926(5) 0.0602(14) Uani 1 1 d . . . H2 H 0.408(6) 0.574(6) 1.189(5) 0.060(15) Uiso 1 1 d . . . H4 H 0.500(6) 0.168(6) 1.141(5) 0.065(15) Uiso 1 1 d . . . H5 H 0.329(6) 0.204(6) 0.958(5) 0.060(14) Uiso 1 1 d . . . H61 H 0.671(7) 0.365(6) 1.341(5) 0.069(17) Uiso 1 1 d . . . H62 H 0.599(7) 0.516(8) 1.347(6) 0.09(2) Uiso 1 1 d . . . H71 H 0.417(12) 0.338(11) 1.417(9) 0.17(4) Uiso 1 1 d . . . H72 H 0.589(8) 0.340(7) 1.485(7) 0.10(2) Uiso 1 1 d . . . H73 H 0.495(8) 0.186(9) 1.365(6) 0.12(2) Uiso 1 1 d . . . H81 H 0.245(7) 0.488(7) 0.901(6) 0.09(2) Uiso 1 1 d . . . H82 H 0.208(7) 0.573(8) 1.005(5) 0.08(2) Uiso 1 1 d . . . H83 H 0.117(9) 0.426(8) 0.956(6) 0.11(2) Uiso 1 1 d . . . H91 H 0.177(8) -0.016(7) 0.558(5) 0.08(2) Uiso 1 1 d . . . H92 H 0.311(13) -0.035(14) 0.512(11) 0.20(5) Uiso 1 1 d . . . H93 H 0.248(6) 0.120(6) 0.494(5) 0.075(17) Uiso 1 1 d . . . H101 H 0.812(6) 0.024(7) 1.881(5) 0.074(16) Uiso 1 1 d . . . H102 H 0.719(5) 0.162(5) 1.892(4) 0.044(12) Uiso 1 1 d . . . H111 H 0.987(6) 0.154(5) 1.773(4) 0.051(13) Uiso 1 1 d . . . H112 H 0.818(6) 0.114(6) 1.703(5) 0.065(15) Uiso 1 1 d . . . H121 H 0.878(6) 0.324(6) 1.607(5) 0.068(15) Uiso 1 1 d . . . H122 H 1.056(6) 0.374(5) 1.681(4) 0.057(14) Uiso 1 1 d . . . H131 H 0.831(6) 0.557(5) 1.678(4) 0.041(12) Uiso 1 1 d . . . H132 H 0.958(6) 0.582(6) 1.600(5) 0.074(16) Uiso 1 1 d . . . H141 H 0.978(5) 0.177(5) 2.270(4) 0.041(12) Uiso 1 1 d . . . H142 H 1.106(8) 0.225(7) 2.185(6) 0.09(2) Uiso 1 1 d . . . H151 H 0.781(6) 0.159(5) 2.103(4) 0.050(13) Uiso 1 1 d . . . H152 H 0.888(7) 0.029(7) 2.083(5) 0.084(18) 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 S 0.0469(7) 0.0530(7) 0.0415(6) 0.0003(5) -0.0047(5) 0.0107(6) O1 0.093(3) 0.113(3) 0.080(3) -0.016(3) -0.001(2) 0.058(3) O2 0.143(4) 0.070(3) 0.078(3) 0.028(2) -0.019(3) 0.019(3) O3 0.062(2) 0.111(3) 0.074(3) 0.004(2) 0.006(2) -0.010(2) O4 0.0461(17) 0.0420(17) 0.0577(19) 0.0022(15) 0.0015(15) 0.0019(14) O5 0.0512(19) 0.0483(18) 0.056(2) -0.0050(15) -0.0022(16) 0.0104(15) O6 0.057(2) 0.0499(18) 0.058(2) 0.0027(15) 0.0008(16) 0.0176(16) N1 0.051(2) 0.058(2) 0.049(2) 0.0051(19) -0.0078(19) 0.012(2) N3 0.0393(19) 0.040(2) 0.042(2) 0.0032(16) 0.0010(16) 0.0024(16) C2 0.050(3) 0.048(3) 0.047(3) 0.002(2) 0.001(2) 0.008(2) C4 0.050(3) 0.047(3) 0.059(3) 0.008(2) 0.007(2) 0.013(2) C5 0.045(3) 0.038(2) 0.053(3) 0.004(2) 0.004(2) 0.004(2) C6 0.088(5) 0.083(5) 0.060(4) 0.006(3) -0.018(3) 0.022(4) C7 0.114(7) 0.105(6) 0.065(4) 0.019(4) 0.014(4) 0.030(5) C8 0.048(3) 0.053(3) 0.052(3) 0.011(3) -0.004(2) 0.011(3) C9 0.076(4) 0.082(5) 0.057(3) -0.003(3) -0.016(3) -0.008(4) C10 0.050(3) 0.044(3) 0.073(4) -0.010(3) -0.005(3) 0.000(3) C11 0.059(3) 0.044(3) 0.062(3) -0.011(2) -0.003(3) 0.011(2) C12 0.063(4) 0.073(4) 0.046(3) -0.005(3) -0.009(3) 0.019(3) C13 0.067(4) 0.077(4) 0.048(3) 0.010(3) -0.001(3) 0.025(3) C14 0.067(4) 0.053(3) 0.071(4) 0.024(3) 0.018(3) 0.017(3) C15 0.053(3) 0.049(3) 0.078(4) 0.006(3) 0.010(3) 0.008(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 S O1 1.430(4) . ? S O2 1.431(4) . ? S O3 1.441(4) . ? S C9 1.747(6) . ? O4 C15 1.415(7) . ? O4 C10 1.423(6) . ? O5 C12 1.424(7) . ? O5 C11 1.429(6) . ? O6 C13 1.413(6) . ? O6 C14 1.414(6) 2_769 ? N1 C2 1.327(6) . ? N1 C4 1.364(6) . ? N1 C6 1.464(7) . ? N3 C2 1.318(6) . ? N3 C5 1.374(6) . ? N3 C8 1.470(6) . ? C2 H2 0.91(5) . ? C4 C5 1.327(7) . ? C4 H4 0.90(5) . ? C5 H5 0.93(5) . ? C6 C7 1.496(10) . ? C6 H61 0.87(6) . ? C6 H62 0.99(7) . ? C7 H61 1.61(6) . ? C7 H71 0.96(10) . ? C7 H72 0.99(7) . ? C7 H73 1.24(8) . ? C8 H81 0.86(7) . ? C8 H82 0.91(7) . ? C8 H83 0.94(8) . ? C9 H91 0.92(7) . ? C9 H92 0.94(13) . ? C9 H93 1.02(6) . ? C10 C11 1.479(8) . ? C10 H101 0.94(6) . ? C10 H102 1.00(5) . ? C11 H111 0.98(5) . ? C11 H112 1.00(5) . ? C12 C13 1.494(8) . ? C12 H121 0.95(6) . ? C12 H122 1.01(5) . ? C13 H131 0.89(5) . ? C13 H132 1.04(6) . ? C14 O6 1.414(6) 2_769 ? C14 C15 1.489(8) . ? C14 H141 0.92(5) . ? C14 H142 1.04(7) . ? C15 H151 0.97(5) . ? C15 H152 1.00(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S O2 112.6(3) . . ? O1 S O3 110.2(3) . . ? O2 S O3 114.0(3) . . ? O1 S C9 106.9(3) . . ? O2 S C9 107.0(3) . . ? O3 S C9 105.6(4) . . ? C15 O4 C10 110.5(4) . . ? C12 O5 C11 111.9(4) . . ? C13 O6 C14 113.3(4) . 2_769 ? C2 N1 C4 109.0(4) . . ? C2 N1 C6 125.8(5) . . ? C4 N1 C6 125.1(5) . . ? C2 N3 C5 108.5(4) . . ? C2 N3 C8 125.6(4) . . ? C5 N3 C8 125.9(4) . . ? N3 C2 N1 107.9(4) . . ? N3 C2 H2 126(3) . . ? N1 C2 H2 126(3) . . ? C5 C4 N1 107.1(4) . . ? C5 C4 H4 131(3) . . ? N1 C4 H4 122(3) . . ? C4 C5 N3 107.4(4) . . ? C4 C5 H5 127(3) . . ? N3 C5 H5 125(3) . . ? N1 C6 C7 108.9(6) . . ? N1 C6 H61 130(4) . . ? C7 C6 H61 81(4) . . ? N1 C6 H62 106(4) . . ? C7 C6 H62 108(4) . . ? H61 C6 H62 117(5) . . ? C6 C7 H61 32(2) . . ? C6 C7 H71 116(6) . . ? H61 C7 H71 147(6) . . ? C6 C7 H72 111(4) . . ? H61 C7 H72 90(5) . . ? H71 C7 H72 108(7) . . ? C6 C7 H73 110(3) . . ? H61 C7 H73 97(4) . . ? H71 C7 H73 101(7) . . ? H72 C7 H73 110(5) . . ? N3 C8 H81 115(4) . . ? N3 C8 H82 111(4) . . ? H81 C8 H82 107(6) . . ? N3 C8 H83 113(4) . . ? H81 C8 H83 106(6) . . ? H82 C8 H83 104(6) . . ? S C9 H91 112(4) . . ? S C9 H92 114(7) . . ? H91 C9 H92 95(7) . . ? S C9 H93 113(3) . . ? H91 C9 H93 112(5) . . ? H92 C9 H93 110(8) . . ? O4 C10 C11 109.7(4) . . ? O4 C10 H101 106(3) . . ? C11 C10 H101 110(4) . . ? O4 C10 H102 111(3) . . ? C11 C10 H102 111(2) . . ? H101 C10 H102 109(4) . . ? O5 C11 C10 110.1(4) . . ? O5 C11 H111 108(3) . . ? C10 C11 H111 112(3) . . ? O5 C11 H112 113(3) . . ? C10 C11 H112 110(3) . . ? H111 C11 H112 103(4) . . ? O5 C12 C13 109.3(5) . . ? O5 C12 H121 107(3) . . ? C13 C12 H121 110(3) . . ? O5 C12 H122 111(3) . . ? C13 C12 H122 106(3) . . ? H121 C12 H122 113(4) . . ? O6 C13 C12 109.7(4) . . ? O6 C13 H131 113(3) . . ? C12 C13 H131 109(3) . . ? O6 C13 H132 109(3) . . ? C12 C13 H132 112(3) . . ? H131 C13 H132 104(4) . . ? O6 C14 C15 110.0(4) 2_769 . ? O6 C14 H141 109(3) 2_769 . ? C15 C14 H141 113(3) . . ? O6 C14 H142 104(4) 2_769 . ? C15 C14 H142 108(4) . . ? H141 C14 H142 112(4) . . ? O4 C15 C14 109.5(5) . . ? O4 C15 H151 112(3) . . ? C14 C15 H151 106(3) . . ? O4 C15 H152 107(3) . . ? C14 C15 H152 111(3) . . ? H151 C15 H152 110(4) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.391 _refine_diff_density_min -0.282 _refine_diff_density_rms 0.057