Supplementary Material (ESI) for Green Chemistry This journal is © The Royal Society of Chemistry 2007 data_global _journal_name_full 'Green Chemistry' _journal_coden_cambridge 1048 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Francine Agbossou-Niedercorn' _publ_contact_author_email FRANCINE.AGBOSSOU@ENSC-LILLE.FR loop_ _publ_author_name F.Agbossou-Niedercorn L.Leclercq G.Nowogrocki I.Suisse # Attachment 'B703096G_Agbossou_compound_16_Green_Chem_070523.txt' data_ionicim _database_code_depnum_ccdc_archive 'CCDC 290114' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; 3-methyl-1-(tetrahydro-2H-pyran-2-ylmethyl)-1H-imidazol-3-ium trifluoromethanesulfonate ; _chemical_melting_point 85 _chemical_formula_moiety ? _chemical_formula_sum 'C11 H17 F3 N2 O4 S' _chemical_formula_weight 330.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 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 8.5166(14) _cell_length_b 10.8790(18) _cell_length_c 16.006(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.000(3) _cell_angle_gamma 90.00 _cell_volume 1445.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'irregular prismatic' _exptl_crystal_colour colorless _exptl_crystal_size_max .6 _exptl_crystal_size_mid .5 _exptl_crystal_size_min .3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.518 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.275 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11172 _diffrn_reflns_av_R_equivalents 0.0234 _diffrn_reflns_av_sigmaI/netI 0.0208 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 28.21 _reflns_number_total 3237 _reflns_number_gt 2885 _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^)+(0.0542P)^2^+0.6207P] 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 3237 _refine_ls_number_parameters 258 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0394 _refine_ls_R_factor_gt 0.0350 _refine_ls_wR_factor_ref 0.0968 _refine_ls_wR_factor_gt 0.0933 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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 N1 N 1.28363(14) 0.81826(11) 0.36757(7) 0.0192(2) Uani 1 1 d . . . C2 C 1.20537(17) 0.71337(13) 0.34726(9) 0.0202(3) Uani 1 1 d . . . H2 H 1.220(2) 0.6623(18) 0.3043(12) 0.029(5) Uiso 1 1 d . . . N3 N 1.10417(14) 0.69768(11) 0.39883(7) 0.0188(2) Uani 1 1 d . . . C4 C 1.11841(17) 0.79707(13) 0.45353(9) 0.0212(3) Uani 1 1 d . . . H4 H 1.056(2) 0.8009(16) 0.4933(12) 0.023(4) Uiso 1 1 d . . . C5 C 1.23064(17) 0.87236(14) 0.43404(9) 0.0216(3) Uani 1 1 d . . . H5 H 1.270(2) 0.9454(17) 0.4566(11) 0.022(4) Uiso 1 1 d . . . C6 C 0.99218(18) 0.59429(14) 0.39631(9) 0.0234(3) Uani 1 1 d . . . H6A H 1.054(2) 0.5164(18) 0.3947(11) 0.027(5) Uiso 1 1 d . . . H6B H 0.956(2) 0.5955(17) 0.4494(12) 0.026(4) Uiso 1 1 d . . . C7 C 0.84944(17) 0.60207(13) 0.32081(9) 0.0205(3) Uani 1 1 d . . . H7 H 0.787(2) 0.6785(19) 0.3226(12) 0.033(5) Uiso 1 1 d . . . O O 0.91393(12) 0.60625(10) 0.24666(6) 0.0231(2) Uani 1 1 d . . . C8 C 0.7905(2) 0.61832(16) 0.16987(10) 0.0285(3) Uani 1 1 d . . . H8A H 0.735(2) 0.6922(19) 0.1720(12) 0.027(5) Uiso 1 1 d . . . H8B H 0.843(3) 0.621(2) 0.1229(14) 0.042(6) Uiso 1 1 d . . . C9 C 0.67297(18) 0.51168(15) 0.15845(10) 0.0255(3) Uani 1 1 d . . . H9A H 0.588(2) 0.5269(17) 0.1069(12) 0.028(5) Uiso 1 1 d . . . H9B H 0.730(2) 0.4339(19) 0.1482(12) 0.032(5) Uiso 1 1 d . . . C10 C 0.60354(18) 0.49681(16) 0.23719(10) 0.0275(3) Uani 1 1 d . . . H10A H 0.531(3) 0.565(2) 0.2401(13) 0.039(5) Uiso 1 1 d . . . H10B H 0.542(2) 0.422(2) 0.2330(13) 0.035(5) Uiso 1 1 d . . . C11 C 0.73879(19) 0.49240(16) 0.31791(10) 0.0273(3) Uani 1 1 d . . . H11A H 0.802(2) 0.417(2) 0.3192(13) 0.035(5) Uiso 1 1 d . . . H11B H 0.695(3) 0.494(2) 0.3688(14) 0.044(6) Uiso 1 1 d . . . C12 C 1.41100(18) 0.86673(16) 0.32858(10) 0.0251(3) Uani 1 1 d . . . H12A H 1.413(2) 0.8224(18) 0.2791(13) 0.030(5) Uiso 1 1 d . . . H12B H 1.514(2) 0.8571(18) 0.3682(12) 0.029(5) Uiso 1 1 d . . . H12C H 1.392(2) 0.9520(19) 0.3178(12) 0.032(5) Uiso 1 1 d . . . S1 S 0.26757(4) 0.72618(3) 0.08521(2) 0.01943(11) Uani 1 1 d . . . O1 O 0.23066(14) 0.66058(11) 0.15618(7) 0.0289(3) Uani 1 1 d . . . O2 O 0.42108(13) 0.78852(10) 0.10351(8) 0.0300(3) Uani 1 1 d . . . O3 O 0.23060(15) 0.66237(11) 0.00456(7) 0.0313(3) Uani 1 1 d . . . C(T) C 0.12503(17) 0.85358(14) 0.06873(10) 0.0242(3) Uani 1 1 d . . . F1 F 0.14247(12) 0.92312(10) 0.13866(7) 0.0403(3) Uani 1 1 d . . . F2 F -0.02706(11) 0.81495(10) 0.04871(7) 0.0363(2) Uani 1 1 d . . . F3 F 0.14808(14) 0.92613(10) 0.00588(8) 0.0449(3) 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 N1 0.0179(6) 0.0213(6) 0.0182(6) 0.0006(4) 0.0037(4) -0.0007(4) C2 0.0199(7) 0.0219(7) 0.0186(7) -0.0012(5) 0.0041(5) -0.0011(5) N3 0.0182(5) 0.0217(6) 0.0165(6) 0.0003(4) 0.0041(4) -0.0019(4) C4 0.0215(7) 0.0243(7) 0.0182(7) -0.0023(5) 0.0056(5) 0.0015(5) C5 0.0237(7) 0.0207(7) 0.0200(7) -0.0022(5) 0.0041(5) -0.0006(5) C6 0.0236(7) 0.0249(7) 0.0214(7) 0.0020(6) 0.0046(6) -0.0063(6) C7 0.0199(7) 0.0222(7) 0.0203(7) -0.0014(5) 0.0062(5) -0.0021(5) O 0.0190(5) 0.0314(6) 0.0187(5) 0.0021(4) 0.0042(4) -0.0041(4) C8 0.0267(8) 0.0339(9) 0.0222(7) 0.0059(6) -0.0003(6) -0.0083(7) C9 0.0229(7) 0.0299(8) 0.0224(7) -0.0013(6) 0.0021(6) -0.0051(6) C10 0.0200(7) 0.0339(8) 0.0291(8) -0.0048(6) 0.0068(6) -0.0073(6) C11 0.0275(8) 0.0323(8) 0.0235(7) -0.0005(6) 0.0086(6) -0.0113(6) C12 0.0214(7) 0.0318(8) 0.0233(7) 0.0003(6) 0.0074(6) -0.0067(6) S1 0.02103(19) 0.01950(19) 0.01906(19) 0.00029(12) 0.00726(13) 0.00234(12) O1 0.0347(6) 0.0294(6) 0.0253(6) 0.0066(4) 0.0125(5) 0.0033(5) O2 0.0193(5) 0.0301(6) 0.0424(7) -0.0013(5) 0.0108(5) 0.0010(4) O3 0.0427(7) 0.0283(6) 0.0225(6) -0.0041(4) 0.0068(5) 0.0066(5) C(T) 0.0198(7) 0.0227(7) 0.0318(8) 0.0006(6) 0.0093(6) 0.0004(5) F1 0.0350(6) 0.0346(5) 0.0530(7) -0.0183(5) 0.0138(5) 0.0061(4) F2 0.0179(4) 0.0346(5) 0.0544(6) 0.0003(5) 0.0042(4) 0.0008(4) F3 0.0438(6) 0.0383(6) 0.0590(7) 0.0270(5) 0.0253(5) 0.0165(5) _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 N1 C2 1.3246(19) . ? N1 C5 1.3777(18) . ? N1 C12 1.4658(18) . ? C2 N3 1.3317(18) . ? N3 C4 1.3793(18) . ? N3 C6 1.4694(18) . ? C4 C5 1.348(2) . ? C6 C7 1.511(2) . ? C7 O 1.4162(17) . ? C7 C11 1.515(2) . ? O C8 1.4326(18) . ? C8 C9 1.516(2) . ? C9 C10 1.516(2) . ? C10 C11 1.526(2) . ? S1 O1 1.4351(11) . ? S1 O3 1.4370(11) . ? S1 O2 1.4432(12) . ? S1 C(T) 1.8221(15) . ? C(T) F3 1.3275(18) . ? C(T) F2 1.3305(17) . ? C(T) F1 1.3313(18) . ? 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 C2 N1 C5 108.86(12) . . ? C2 N1 C12 125.82(13) . . ? C5 N1 C12 125.27(13) . . ? N1 C2 N3 108.57(13) . . ? C2 N3 C4 108.44(12) . . ? C2 N3 C6 125.99(12) . . ? C4 N3 C6 125.54(12) . . ? C5 C4 N3 107.17(13) . . ? C4 C5 N1 106.96(13) . . ? N3 C6 C7 112.30(12) . . ? O C7 C6 106.15(11) . . ? O C7 C11 110.83(12) . . ? C6 C7 C11 111.31(12) . . ? C7 O C8 111.96(11) . . ? O C8 C9 111.74(13) . . ? C8 C9 C10 110.59(13) . . ? C9 C10 C11 110.23(13) . . ? C7 C11 C10 110.31(13) . . ? O1 S1 O3 115.35(7) . . ? O1 S1 O2 115.01(7) . . ? O3 S1 O2 114.51(7) . . ? O1 S1 C(T) 103.62(7) . . ? O3 S1 C(T) 103.48(7) . . ? O2 S1 C(T) 102.45(7) . . ? F3 C(T) F2 107.89(13) . . ? F3 C(T) F1 106.96(13) . . ? F2 C(T) F1 107.48(12) . . ? F3 C(T) S1 110.77(10) . . ? F2 C(T) S1 112.05(10) . . ? F1 C(T) S1 111.45(11) . . ? _diffrn_measured_fraction_theta_max 0.908 _diffrn_reflns_theta_full 28.21 _diffrn_measured_fraction_theta_full 0.908 _refine_diff_density_max 0.427 _refine_diff_density_min -0.386 _refine_diff_density_rms 0.054 # Attachment 'B703096G_Agbossou_compound_3_Green_Chem_070523.txt' data_ionicm _database_code_depnum_ccdc_archive 'CCDC 290115' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; 3-methyl-1-(4-(1-methyl-1H-imidazol-3-ium-3-yl)butyl)-1H- imidazol-3-ium bis(trifluoromethanesulfonate) ; _chemical_melting_point 71 _chemical_formula_moiety ? _chemical_formula_sum 'C14 H20 F6 N4 O6 S2' _chemical_formula_weight 518.46 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 8.6516(15) _cell_length_b 10.1699(17) _cell_length_c 12.195(2) _cell_angle_alpha 87.354(3) _cell_angle_beta 85.474(3) _cell_angle_gamma 83.360(3) _cell_volume 1061.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max .45 _exptl_crystal_size_mid .15 _exptl_crystal_size_min .15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.622 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 532 _exptl_absorpt_coefficient_mu 0.343 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8258 _diffrn_reflns_av_R_equivalents 0.0192 _diffrn_reflns_av_sigmaI/netI 0.0289 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 27.94 _reflns_number_total 4396 _reflns_number_gt 3867 _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^)+(0.0482P)^2^+0.5380P] 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 4396 _refine_ls_number_parameters 369 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0394 _refine_ls_R_factor_gt 0.0341 _refine_ls_wR_factor_ref 0.0927 _refine_ls_wR_factor_gt 0.0890 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.001 _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 N1 N 0.29175(17) 0.44445(14) 1.10653(11) 0.0188(3) Uani 1 1 d . . . C2 C 0.1738(2) 0.37738(17) 1.08859(13) 0.0194(3) Uani 1 1 d . . . H2 H 0.072(3) 0.408(2) 1.0990(17) 0.025(5) Uiso 1 1 d . . . N3 N 0.23112(16) 0.25822(14) 1.05426(11) 0.0179(3) Uani 1 1 d . . . C4 C 0.3917(2) 0.24902(18) 1.04934(15) 0.0222(4) Uani 1 1 d . . . H4 H 0.451(3) 0.175(2) 1.0269(18) 0.032(6) Uiso 1 1 d . . . C5 C 0.4294(2) 0.36561(18) 1.08198(14) 0.0219(4) Uani 1 1 d . . . H5 H 0.527(3) 0.396(2) 1.0910(19) 0.036(6) Uiso 1 1 d . . . N1' N 0.24335(17) 0.35487(14) 0.49174(11) 0.0205(3) Uani 1 1 d . . . C2' C 0.3002(2) 0.27718(17) 0.57363(14) 0.0195(3) Uani 1 1 d . . . H2' H 0.404(3) 0.266(2) 0.5948(18) 0.033(6) Uiso 1 1 d . . . N3' N 0.18509(16) 0.21532(14) 0.62266(11) 0.0177(3) Uani 1 1 d . . . C4' C 0.0500(2) 0.25522(17) 0.57106(14) 0.0206(3) Uani 1 1 d . . . H4' H -0.042(2) 0.225(2) 0.5926(17) 0.024(5) Uiso 1 1 d . . . C5' C 0.0868(2) 0.34209(17) 0.48915(14) 0.0212(3) Uani 1 1 d . . . H5' H 0.025(3) 0.388(2) 0.4357(18) 0.030(6) Uiso 1 1 d . . . C6 C 0.1348(2) 0.15245(18) 1.03234(15) 0.0209(3) Uani 1 1 d . . . H6A H 0.026(2) 0.195(2) 1.0339(16) 0.024(5) Uiso 1 1 d . . . H6B H 0.147(2) 0.087(2) 1.0916(18) 0.028(5) Uiso 1 1 d . . . C7 C 0.1835(2) 0.09106(17) 0.92201(14) 0.0199(3) Uani 1 1 d . . . H7A H 0.286(3) 0.046(2) 0.9227(17) 0.027(5) Uiso 1 1 d . . . H7B H 0.118(3) 0.025(2) 0.9138(17) 0.028(5) Uiso 1 1 d . . . C8 C 0.1737(2) 0.19190(17) 0.82560(14) 0.0190(3) Uani 1 1 d . . . H8A H 0.252(2) 0.251(2) 0.8277(16) 0.020(5) Uiso 1 1 d . . . H8B H 0.069(2) 0.243(2) 0.8304(17) 0.024(5) Uiso 1 1 d . . . C9 C 0.2002(2) 0.12137(17) 0.71779(14) 0.0196(3) Uani 1 1 d . . . H9A H 0.129(2) 0.062(2) 0.7120(16) 0.020(5) Uiso 1 1 d . . . H9B H 0.301(2) 0.077(2) 0.7111(16) 0.021(5) Uiso 1 1 d . . . C10 C 0.2753(2) 0.58162(18) 1.14222(16) 0.0242(4) Uani 1 1 d . . . H10A H 0.261(2) 0.642(2) 1.0762(18) 0.026(5) Uiso 1 1 d . . . H10B H 0.365(3) 0.592(2) 1.1784(17) 0.025(5) Uiso 1 1 d . . . H10C H 0.186(3) 0.597(2) 1.1914(19) 0.033(6) Uiso 1 1 d . . . C11 C 0.3349(3) 0.4360(2) 0.41517(17) 0.0312(4) Uani 1 1 d . . . H11A H 0.332(3) 0.405(3) 0.344(2) 0.052(7) Uiso 1 1 d . . . H11B H 0.292(3) 0.529(3) 0.421(2) 0.048(7) Uiso 1 1 d . . . H11C H 0.445(3) 0.426(3) 0.437(2) 0.047(7) Uiso 1 1 d . . . S1 S 0.22250(5) 0.56152(4) 0.76453(3) 0.01679(11) Uani 1 1 d . . . O1 O 0.09000(14) 0.51598(12) 0.71861(10) 0.0218(3) Uani 1 1 d . . . O2 O 0.37278(14) 0.49428(12) 0.73041(11) 0.0245(3) Uani 1 1 d . . . O3 O 0.19899(14) 0.58563(13) 0.88115(10) 0.0241(3) Uani 1 1 d . . . C1T C 0.2280(2) 0.72823(18) 0.70245(15) 0.0251(4) Uani 1 1 d . . . F1 F 0.09360(14) 0.80359(11) 0.72486(11) 0.0376(3) Uani 1 1 d . . . F2 F 0.25258(15) 0.72445(13) 0.59300(10) 0.0394(3) Uani 1 1 d . . . F3 F 0.34236(14) 0.78753(11) 0.73950(11) 0.0389(3) Uani 1 1 d . . . S2 S 0.32051(5) 0.89265(4) 1.25541(3) 0.01970(11) Uani 1 1 d . . . O4 O 0.16719(14) 0.88977(13) 1.21758(11) 0.0249(3) Uani 1 1 d . . . O5 O 0.37030(17) 0.78170(13) 1.32747(12) 0.0337(3) Uani 1 1 d . . . O6 O 0.43597(16) 0.93131(15) 1.17275(12) 0.0346(3) Uani 1 1 d . . . C2T C 0.2935(2) 1.03047(18) 1.34872(15) 0.0241(4) Uani 1 1 d . . . F4 F 0.25009(14) 1.14541(11) 1.29544(10) 0.0338(3) Uani 1 1 d . . . F5 F 0.18335(16) 1.01192(12) 1.42862(10) 0.0407(3) Uani 1 1 d . . . F6 F 0.42446(15) 1.04434(12) 1.39561(10) 0.0400(3) 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 N1 0.0201(7) 0.0201(7) 0.0163(7) -0.0017(5) -0.0018(5) -0.0020(6) C2 0.0183(8) 0.0228(8) 0.0166(8) 0.0013(6) 0.0003(6) -0.0019(7) N3 0.0167(7) 0.0202(7) 0.0172(7) 0.0000(5) -0.0024(5) -0.0027(5) C4 0.0183(8) 0.0222(9) 0.0259(9) -0.0020(7) -0.0028(7) -0.0004(7) C5 0.0189(9) 0.0245(9) 0.0229(9) -0.0013(7) -0.0053(7) -0.0023(7) N1' 0.0231(8) 0.0217(7) 0.0168(7) -0.0017(5) -0.0007(6) -0.0033(6) C2' 0.0201(9) 0.0199(8) 0.0184(8) -0.0031(6) -0.0013(6) -0.0016(6) N3' 0.0185(7) 0.0177(7) 0.0171(7) -0.0015(5) -0.0026(5) -0.0010(5) C4' 0.0180(8) 0.0223(8) 0.0221(9) -0.0034(7) -0.0033(7) -0.0024(7) C5' 0.0213(9) 0.0230(9) 0.0196(8) -0.0031(7) -0.0056(7) -0.0006(7) C6 0.0191(9) 0.0232(9) 0.0219(9) 0.0025(7) -0.0030(7) -0.0087(7) C7 0.0227(9) 0.0178(8) 0.0200(8) 0.0013(6) -0.0041(7) -0.0047(7) C8 0.0216(9) 0.0171(8) 0.0188(8) 0.0008(6) -0.0034(6) -0.0034(7) C9 0.0216(9) 0.0165(8) 0.0203(8) 0.0018(6) -0.0019(7) -0.0015(7) C10 0.0283(10) 0.0212(9) 0.0234(9) -0.0051(7) -0.0027(8) -0.0023(7) C11 0.0398(12) 0.0336(11) 0.0208(10) 0.0053(8) 0.0017(8) -0.0125(9) S1 0.0160(2) 0.0172(2) 0.0172(2) 0.00010(15) -0.00176(15) -0.00200(15) O1 0.0214(6) 0.0235(6) 0.0215(6) -0.0006(5) -0.0049(5) -0.0049(5) O2 0.0187(6) 0.0238(6) 0.0304(7) -0.0030(5) 0.0007(5) 0.0001(5) O3 0.0217(6) 0.0349(7) 0.0165(6) -0.0027(5) -0.0025(5) -0.0044(5) C1T 0.0247(9) 0.0224(9) 0.0288(10) 0.0034(7) -0.0068(7) -0.0035(7) F1 0.0302(6) 0.0220(6) 0.0597(8) 0.0009(5) -0.0089(6) 0.0039(5) F2 0.0428(7) 0.0446(7) 0.0302(6) 0.0174(5) -0.0032(5) -0.0098(6) F3 0.0350(7) 0.0260(6) 0.0597(8) 0.0066(5) -0.0171(6) -0.0148(5) S2 0.0167(2) 0.0199(2) 0.0227(2) -0.00485(16) -0.00267(16) -0.00040(15) O4 0.0193(6) 0.0270(7) 0.0294(7) -0.0004(5) -0.0066(5) -0.0046(5) O5 0.0414(8) 0.0222(7) 0.0382(8) -0.0034(6) -0.0185(7) 0.0050(6) O6 0.0263(7) 0.0418(8) 0.0365(8) -0.0150(6) 0.0113(6) -0.0115(6) C2T 0.0277(9) 0.0220(9) 0.0222(9) -0.0034(7) -0.0008(7) -0.0012(7) F4 0.0459(7) 0.0193(5) 0.0351(6) -0.0023(4) -0.0034(5) 0.0013(5) F5 0.0522(8) 0.0366(7) 0.0306(6) -0.0086(5) 0.0168(5) -0.0046(6) F6 0.0447(7) 0.0390(7) 0.0401(7) -0.0153(5) -0.0182(6) -0.0051(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.328(2) . ? N1 C5 1.377(2) . ? N1 C10 1.468(2) . ? C2 N3 1.328(2) . ? N3 C4 1.378(2) . ? N3 C6 1.480(2) . ? C4 C5 1.351(3) . ? N1' C2' 1.334(2) . ? N1' C5' 1.379(2) . ? N1' C11 1.464(2) . ? C2' N3' 1.327(2) . ? N3' C4' 1.382(2) . ? N3' C9 1.473(2) . ? C4' C5' 1.346(3) . ? C6 C7 1.518(2) . ? C7 C8 1.525(2) . ? C8 C9 1.516(2) . ? S1 O2 1.4375(13) . ? S1 O1 1.4458(12) . ? S1 O3 1.4488(12) . ? S1 C1T 1.8288(19) . ? C1T F1 1.333(2) . ? C1T F3 1.334(2) . ? C1T F2 1.336(2) . ? S2 O6 1.4366(14) . ? S2 O4 1.4422(13) . ? S2 O5 1.4445(14) . ? S2 C2T 1.8285(18) . ? C2T F5 1.331(2) . ? C2T F6 1.333(2) . ? C2T F4 1.340(2) . ? 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 C2 N1 C5 108.53(14) . . ? C2 N1 C10 124.86(15) . . ? C5 N1 C10 126.56(15) . . ? N1 C2 N3 108.72(15) . . ? C2 N3 C4 108.61(15) . . ? C2 N3 C6 124.36(15) . . ? C4 N3 C6 126.93(15) . . ? C5 C4 N3 106.95(16) . . ? C4 C5 N1 107.18(16) . . ? C2' N1' C5' 108.78(14) . . ? C2' N1' C11 125.06(16) . . ? C5' N1' C11 126.12(16) . . ? N3' C2' N1' 108.21(15) . . ? C2' N3' C4' 108.92(14) . . ? C2' N3' C9 124.97(15) . . ? C4' N3' C9 126.10(15) . . ? C5' C4' N3' 106.96(15) . . ? C4' C5' N1' 107.13(15) . . ? N3 C6 C7 112.02(14) . . ? C6 C7 C8 112.94(14) . . ? C9 C8 C7 109.97(14) . . ? N3' C9 C8 111.53(14) . . ? O2 S1 O1 116.06(8) . . ? O2 S1 O3 114.63(8) . . ? O1 S1 O3 114.08(7) . . ? O2 S1 C1T 103.62(8) . . ? O1 S1 C1T 103.22(8) . . ? O3 S1 C1T 102.84(8) . . ? F1 C1T F3 108.17(15) . . ? F1 C1T F2 107.57(15) . . ? F3 C1T F2 107.64(15) . . ? F1 C1T S1 111.11(13) . . ? F3 C1T S1 111.19(12) . . ? F2 C1T S1 111.00(13) . . ? O6 S2 O4 114.92(9) . . ? O6 S2 O5 115.90(9) . . ? O4 S2 O5 114.29(8) . . ? O6 S2 C2T 103.52(9) . . ? O4 S2 C2T 103.43(8) . . ? O5 S2 C2T 102.28(8) . . ? F5 C2T F6 107.86(15) . . ? F5 C2T F4 107.55(15) . . ? F6 C2T F4 107.38(15) . . ? F5 C2T S2 110.87(13) . . ? F6 C2T S2 111.65(12) . . ? F4 C2T S2 111.34(12) . . ? _diffrn_measured_fraction_theta_max 0.861 _diffrn_reflns_theta_full 27.94 _diffrn_measured_fraction_theta_full 0.861 _refine_diff_density_max 0.419 _refine_diff_density_min -0.398 _refine_diff_density_rms 0.057 data_ionicjjm _database_code_depnum_ccdc_archive 'CCDC 621900' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; 1-methyl-3-(tetrahydrofuran-3-ylmethyl)-1H-imidazol-3-ium trifluoromethanesulfonate / tetrabuthylammonium trifluoromethanesulfonate ; _chemical_melting_point 95 _chemical_formula_moiety ? _chemical_formula_sum 'C27 H51 F6 N3 O7 S2' _chemical_formula_weight 707.83 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 9.5883(13) _cell_length_b 9.7729(13) _cell_length_c 19.198(3) _cell_angle_alpha 85.627(2) _cell_angle_beta 88.693(2) _cell_angle_gamma 88.563(2) _cell_volume 1792.7(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description irregular _exptl_crystal_colour colorless _exptl_crystal_size_max .4 _exptl_crystal_size_mid .35 _exptl_crystal_size_min .25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.223 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14089 _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_sigmaI/netI 0.0491 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 28.93 _reflns_number_total 7772 _reflns_number_gt 5727 _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^)+(0.0935P)^2^+0.3212P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7772 _refine_ls_number_parameters 411 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0786 _refine_ls_R_factor_gt 0.0578 _refine_ls_wR_factor_ref 0.1722 _refine_ls_wR_factor_gt 0.1570 _refine_ls_goodness_of_fit_ref 1.124 _refine_ls_restrained_S_all 1.124 _refine_ls_shift/su_max 0.003 _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 N1 N 0.8410(2) 0.6397(2) 0.31297(11) 0.0247(5) Uani 1 1 d . . . C1 C 0.7362(3) 0.6509(3) 0.26892(13) 0.0250(5) Uani 1 1 d . . . H1 H 0.6741 0.5822 0.2613 0.030 Uiso 1 1 calc R . . N2 N 0.7346(2) 0.7771(2) 0.23733(11) 0.0223(4) Uani 1 1 d . . . C2 C 0.8415(3) 0.8492(3) 0.26275(13) 0.0237(5) Uani 1 1 d . . . H2 H 0.8634 0.9399 0.2499 0.028 Uiso 1 1 calc R . . C3 C 0.9088(3) 0.7628(3) 0.31000(13) 0.0243(5) Uani 1 1 d . . . H3 H 0.9860 0.7828 0.3356 0.029 Uiso 1 1 calc R . . C4 C 0.6440(3) 0.8242(3) 0.17904(13) 0.0232(5) Uani 1 1 d . . . H4A H 0.6017 0.9127 0.1877 0.028 Uiso 1 1 calc R . . H4B H 0.5699 0.7596 0.1755 0.028 Uiso 1 1 calc R . . C5 C 0.7276(3) 0.8365(3) 0.11158(14) 0.0297(6) Uani 1 1 d . . . H5 H 0.8017 0.9027 0.1151 0.036 Uiso 1 1 calc R . . C6 C 0.6383(3) 0.8805(4) 0.04841(16) 0.0486(9) Uani 1 1 d . . . H6A H 0.5418 0.8558 0.0576 0.058 Uiso 1 1 calc R . . H6B H 0.6419 0.9790 0.0377 0.058 Uiso 1 1 calc R . . O O 0.6962(3) 0.8089(3) -0.00876(12) 0.0659(8) Uani 1 1 d . . . C7 C 0.8144(4) 0.7254(4) 0.01459(19) 0.0595(10) Uani 1 1 d . . . H7A H 0.9007 0.7734 0.0044 0.071 Uiso 1 1 calc R . . H7B H 0.8184 0.6398 -0.0079 0.071 Uiso 1 1 calc R . . C8 C 0.7917(3) 0.7002(3) 0.09017(17) 0.0385(7) Uani 1 1 d . . . H8A H 0.8790 0.6788 0.1136 0.046 Uiso 1 1 calc R . . H8B H 0.7282 0.6253 0.1008 0.046 Uiso 1 1 calc R . . C9 C 0.8768(3) 0.5158(3) 0.35815(15) 0.0338(6) Uani 1 1 d . . . H9A H 0.8230 0.5159 0.4010 0.051 Uiso 1 1 calc R . . H9B H 0.9744 0.5150 0.3683 0.051 Uiso 1 1 calc R . . H9C H 0.8562 0.4356 0.3347 0.051 Uiso 1 1 calc R . . N3 N 0.30201(19) 0.17855(19) 0.27804(10) 0.0165(4) Uani 1 1 d . . . C10 C 0.2538(2) 0.3103(2) 0.23664(12) 0.0182(5) Uani 1 1 d . . . H10A H 0.1607 0.2971 0.2200 0.022 Uiso 1 1 calc R . . H10B H 0.2476 0.3835 0.2680 0.022 Uiso 1 1 calc R . . C11 C 0.3468(3) 0.3560(2) 0.17456(13) 0.0231(5) Uani 1 1 d . . . H11A H 0.3438 0.2896 0.1396 0.028 Uiso 1 1 calc R . . H11B H 0.4424 0.3604 0.1895 0.028 Uiso 1 1 calc R . . C12 C 0.2988(3) 0.4965(3) 0.14275(13) 0.0263(5) Uani 1 1 d . . . H12A H 0.2037 0.4915 0.1272 0.032 Uiso 1 1 calc R . . H12B H 0.3001 0.5624 0.1780 0.032 Uiso 1 1 calc R . . C13 C 0.3926(3) 0.5449(3) 0.08124(14) 0.0309(6) Uani 1 1 d . . . H13A H 0.4865 0.5515 0.0968 0.046 Uiso 1 1 calc R . . H13B H 0.3601 0.6333 0.0621 0.046 Uiso 1 1 calc R . . H13C H 0.3905 0.4804 0.0460 0.046 Uiso 1 1 calc R . . C14 C 0.4352(2) 0.2068(2) 0.31484(12) 0.0184(5) Uani 1 1 d . . . H14A H 0.4161 0.2802 0.3452 0.022 Uiso 1 1 calc R . . H14B H 0.5037 0.2396 0.2799 0.022 Uiso 1 1 calc R . . C15 C 0.4995(2) 0.0853(2) 0.35823(13) 0.0214(5) Uani 1 1 d . . . H15A H 0.5406 0.0202 0.3275 0.026 Uiso 1 1 calc R . . H15B H 0.4275 0.0391 0.3868 0.026 Uiso 1 1 calc R . . C16 C 0.6111(3) 0.1351(3) 0.40492(14) 0.0277(6) Uani 1 1 d . . . H16A H 0.6790 0.1868 0.3762 0.033 Uiso 1 1 calc R . . H16B H 0.5681 0.1964 0.4370 0.033 Uiso 1 1 calc R . . C17 C 0.6858(3) 0.0177(3) 0.44653(14) 0.0323(6) Uani 1 1 d . . . H17A H 0.6183 -0.0388 0.4718 0.048 Uiso 1 1 calc R . . H17B H 0.7474 0.0541 0.4788 0.048 Uiso 1 1 calc R . . H17C H 0.7388 -0.0365 0.4152 0.048 Uiso 1 1 calc R . . C18 C 0.1873(2) 0.1340(2) 0.33045(12) 0.0196(5) Uani 1 1 d . . . H18A H 0.0997 0.1348 0.3062 0.024 Uiso 1 1 calc R . . H18B H 0.2073 0.0401 0.3481 0.024 Uiso 1 1 calc R . . C19 C 0.1691(2) 0.2218(2) 0.39220(12) 0.0213(5) Uani 1 1 d . . . H19A H 0.1639 0.3181 0.3756 0.026 Uiso 1 1 calc R . . H19B H 0.2487 0.2079 0.4224 0.026 Uiso 1 1 calc R . . C20 C 0.0352(3) 0.1828(3) 0.43327(13) 0.0262(5) Uani 1 1 d . . . H20A H -0.0445 0.2027 0.4036 0.031 Uiso 1 1 calc R . . H20B H 0.0378 0.0849 0.4463 0.031 Uiso 1 1 calc R . . C21 C 0.0173(3) 0.2600(3) 0.49863(14) 0.0348(6) Uani 1 1 d . . . H21A H 0.0964 0.2411 0.5279 0.052 Uiso 1 1 calc R . . H21B H -0.0661 0.2310 0.5236 0.052 Uiso 1 1 calc R . . H21C H 0.0103 0.3567 0.4858 0.052 Uiso 1 1 calc R . . C22 C 0.3312(2) 0.0641(2) 0.23016(12) 0.0182(5) Uani 1 1 d . . . H22A H 0.3603 -0.0176 0.2585 0.022 Uiso 1 1 calc R . . H22B H 0.4088 0.0903 0.1991 0.022 Uiso 1 1 calc R . . C23 C 0.2098(2) 0.0281(3) 0.18614(13) 0.0241(5) Uani 1 1 d . . . H23A H 0.1776 0.1092 0.1582 0.029 Uiso 1 1 calc R . . H23B H 0.1332 -0.0043 0.2163 0.029 Uiso 1 1 calc R . . C24 C 0.2556(3) -0.0831(3) 0.13839(14) 0.0266(6) Uani 1 1 d . . . H24A H 0.3304 -0.0490 0.1074 0.032 Uiso 1 1 calc R . . H24B H 0.2916 -0.1623 0.1665 0.032 Uiso 1 1 calc R . . C25 C 0.1360(3) -0.1269(3) 0.09493(17) 0.0430(8) Uani 1 1 d . . . H25A H 0.0634 -0.1644 0.1254 0.064 Uiso 1 1 calc R . . H25B H 0.1693 -0.1952 0.0648 0.064 Uiso 1 1 calc R . . H25C H 0.0997 -0.0487 0.0672 0.064 Uiso 1 1 calc R . . S1 S 0.31319(6) 0.68312(6) 0.34276(3) 0.02263(16) Uani 1 1 d . . . O1 O 0.2180(2) 0.57359(18) 0.33684(10) 0.0328(4) Uani 1 1 d . . . O2 O 0.2491(2) 0.80572(18) 0.36758(11) 0.0345(5) Uani 1 1 d . . . O3 O 0.4113(2) 0.7065(2) 0.28596(11) 0.0442(5) Uani 1 1 d . . . C1S C 0.4227(3) 0.6182(3) 0.41454(15) 0.0354(7) Uani 1 1 d . . . F1 F 0.5181(2) 0.7076(2) 0.42887(11) 0.0558(5) Uani 1 1 d . . . F2 F 0.4934(2) 0.50442(19) 0.39851(11) 0.0583(6) Uani 1 1 d . . . F3 F 0.3489(2) 0.5896(2) 0.47257(10) 0.0656(6) Uani 1 1 d . . . S2 S 0.77734(6) 0.24286(6) 0.20184(3) 0.02279(16) Uani 1 1 d . . . O4 O 0.67820(19) 0.13913(19) 0.19259(11) 0.0350(5) Uani 1 1 d . . . O5 O 0.7175(2) 0.37127(19) 0.22137(11) 0.0363(5) Uani 1 1 d . . . O6 O 0.8985(2) 0.1945(2) 0.23961(11) 0.0423(5) Uani 1 1 d . . . C2S C 0.8460(3) 0.2832(3) 0.11414(15) 0.0347(6) Uani 1 1 d . . . F4 F 0.9024(2) 0.17141(19) 0.08795(10) 0.0528(5) Uani 1 1 d . . . F5 F 0.9459(2) 0.3769(2) 0.11367(11) 0.0578(6) Uani 1 1 d . . . F6 F 0.7487(2) 0.3338(2) 0.07133(10) 0.0659(6) 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 N1 0.0270(11) 0.0227(11) 0.0243(11) -0.0006(8) -0.0005(9) 0.0013(9) C1 0.0234(12) 0.0221(12) 0.0297(13) -0.0027(10) -0.0024(11) -0.0005(10) N2 0.0222(10) 0.0222(10) 0.0228(10) -0.0028(8) -0.0019(8) 0.0010(8) C2 0.0234(12) 0.0228(12) 0.0252(12) -0.0027(10) -0.0009(10) -0.0029(10) C3 0.0262(13) 0.0254(13) 0.0216(12) -0.0031(10) -0.0004(10) -0.0022(10) C4 0.0212(12) 0.0239(12) 0.0248(12) -0.0035(10) -0.0048(10) 0.0042(10) C5 0.0236(13) 0.0409(16) 0.0252(13) -0.0068(11) -0.0026(11) 0.0024(11) C6 0.0329(16) 0.081(3) 0.0299(16) 0.0053(16) 0.0002(13) 0.0029(16) O 0.0717(18) 0.091(2) 0.0371(13) -0.0170(13) -0.0095(13) 0.0021(16) C7 0.061(2) 0.069(3) 0.050(2) -0.0182(19) 0.0046(19) -0.001(2) C8 0.0260(14) 0.0460(18) 0.0465(17) -0.0227(14) 0.0026(13) -0.0045(13) C9 0.0394(16) 0.0247(14) 0.0363(15) 0.0055(12) -0.0101(13) 0.0028(12) N3 0.0149(9) 0.0159(9) 0.0188(9) -0.0024(7) 0.0005(8) -0.0006(7) C10 0.0173(11) 0.0181(11) 0.0189(11) 0.0000(9) -0.0010(9) 0.0016(9) C11 0.0236(12) 0.0234(12) 0.0216(12) 0.0014(10) 0.0002(10) 0.0009(10) C12 0.0322(14) 0.0219(12) 0.0242(12) 0.0020(10) 0.0024(11) 0.0006(11) C13 0.0351(15) 0.0280(14) 0.0280(13) 0.0093(11) -0.0010(12) -0.0028(11) C14 0.0166(11) 0.0178(11) 0.0208(11) -0.0013(9) -0.0022(9) -0.0018(9) C15 0.0221(12) 0.0199(11) 0.0221(12) -0.0008(9) -0.0018(10) 0.0014(9) C16 0.0252(13) 0.0287(14) 0.0292(13) 0.0020(11) -0.0069(11) -0.0040(11) C17 0.0269(14) 0.0379(16) 0.0313(14) 0.0048(12) -0.0096(12) -0.0004(12) C18 0.0175(11) 0.0185(11) 0.0225(12) 0.0007(9) 0.0017(9) -0.0014(9) C19 0.0228(12) 0.0213(12) 0.0195(11) 0.0000(9) 0.0015(10) 0.0005(9) C20 0.0233(12) 0.0302(14) 0.0242(12) 0.0012(10) 0.0048(10) 0.0028(10) C21 0.0369(15) 0.0427(17) 0.0241(13) -0.0018(12) 0.0053(12) 0.0096(13) C22 0.0169(11) 0.0159(11) 0.0221(11) -0.0047(9) 0.0021(9) 0.0009(9) C23 0.0180(11) 0.0271(13) 0.0283(13) -0.0093(10) -0.0018(10) -0.0004(10) C24 0.0239(13) 0.0281(13) 0.0288(13) -0.0103(11) -0.0042(11) 0.0037(10) C25 0.0332(15) 0.0499(19) 0.0501(18) -0.0308(15) -0.0144(14) 0.0090(14) S1 0.0242(3) 0.0212(3) 0.0220(3) 0.0007(2) -0.0002(2) 0.0015(2) O1 0.0343(10) 0.0228(9) 0.0423(11) -0.0075(8) -0.0059(9) -0.0020(8) O2 0.0344(10) 0.0206(9) 0.0480(12) -0.0015(8) 0.0002(9) 0.0026(8) O3 0.0328(11) 0.0677(15) 0.0299(11) 0.0053(10) 0.0077(9) 0.0046(10) C1S 0.0478(17) 0.0269(14) 0.0318(15) -0.0013(11) -0.0134(13) 0.0034(13) F1 0.0554(12) 0.0487(11) 0.0666(13) -0.0176(10) -0.0323(10) -0.0010(9) F2 0.0682(13) 0.0359(10) 0.0721(14) -0.0100(9) -0.0353(11) 0.0232(9) F3 0.0903(17) 0.0768(15) 0.0273(10) 0.0146(9) -0.0080(10) -0.0043(13) S2 0.0197(3) 0.0223(3) 0.0261(3) -0.0013(2) -0.0012(2) 0.0015(2) O4 0.0270(10) 0.0279(10) 0.0511(12) -0.0111(9) 0.0078(9) -0.0061(8) O5 0.0358(11) 0.0263(10) 0.0480(12) -0.0123(9) 0.0057(9) -0.0003(8) O6 0.0287(11) 0.0548(14) 0.0413(12) 0.0110(10) -0.0103(9) 0.0047(10) C2S 0.0396(16) 0.0329(15) 0.0307(14) 0.0019(12) -0.0005(13) 0.0045(13) F4 0.0683(13) 0.0470(11) 0.0429(10) -0.0102(9) 0.0208(10) 0.0059(10) F5 0.0615(13) 0.0483(12) 0.0618(13) 0.0052(10) 0.0233(11) -0.0185(10) F6 0.0833(16) 0.0762(15) 0.0359(10) 0.0097(10) -0.0182(11) 0.0158(12) _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 N1 C1 1.325(3) . ? N1 C3 1.379(3) . ? N1 C9 1.473(3) . ? C1 N2 1.332(3) . ? C1 H1 0.9300 . ? N2 C2 1.377(3) . ? N2 C4 1.471(3) . ? C2 C3 1.354(4) . ? C2 H2 0.9300 . ? C3 H3 0.9300 . ? C4 C5 1.506(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.529(4) . ? C5 C8 1.534(4) . ? C5 H5 0.9800 . ? C6 O 1.440(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? O C7 1.439(5) . ? C7 C8 1.465(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? N3 C14 1.515(3) . ? N3 C22 1.518(3) . ? N3 C18 1.522(3) . ? N3 C10 1.528(3) . ? C10 C11 1.518(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.524(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.521(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C15 1.523(3) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.524(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.521(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 C19 1.520(3) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.532(3) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.517(4) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 C23 1.518(3) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.524(3) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.523(4) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? S1 O3 1.433(2) . ? S1 O1 1.4368(19) . ? S1 O2 1.4413(19) . ? S1 C1S 1.817(3) . ? C1S F3 1.321(4) . ? C1S F1 1.328(3) . ? C1S F2 1.340(3) . ? S2 O4 1.4305(19) . ? S2 O6 1.434(2) . ? S2 O5 1.4388(19) . ? S2 C2S 1.812(3) . ? C2S F6 1.319(3) . ? C2S F4 1.334(3) . ? C2S F5 1.341(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 C1 N1 C3 108.8(2) . . ? C1 N1 C9 125.1(2) . . ? C3 N1 C9 126.1(2) . . ? N1 C1 N2 108.6(2) . . ? N1 C1 H1 125.7 . . ? N2 C1 H1 125.7 . . ? C1 N2 C2 108.7(2) . . ? C1 N2 C4 124.8(2) . . ? C2 N2 C4 126.1(2) . . ? C3 C2 N2 107.0(2) . . ? C3 C2 H2 126.5 . . ? N2 C2 H2 126.5 . . ? C2 C3 N1 106.9(2) . . ? C2 C3 H3 126.5 . . ? N1 C3 H3 126.5 . . ? N2 C4 C5 110.2(2) . . ? N2 C4 H4A 109.6 . . ? C5 C4 H4A 109.6 . . ? N2 C4 H4B 109.6 . . ? C5 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? C4 C5 C6 112.8(2) . . ? C4 C5 C8 114.1(2) . . ? C6 C5 C8 101.4(2) . . ? C4 C5 H5 109.4 . . ? C6 C5 H5 109.4 . . ? C8 C5 H5 109.4 . . ? O C6 C5 106.1(3) . . ? O C6 H6A 110.5 . . ? C5 C6 H6A 110.5 . . ? O C6 H6B 110.5 . . ? C5 C6 H6B 110.5 . . ? H6A C6 H6B 108.7 . . ? C7 O C6 109.7(2) . . ? O C7 C8 104.8(3) . . ? O C7 H7A 110.8 . . ? C8 C7 H7A 110.8 . . ? O C7 H7B 110.8 . . ? C8 C7 H7B 110.8 . . ? H7A C7 H7B 108.9 . . ? C7 C8 C5 103.2(3) . . ? C7 C8 H8A 111.1 . . ? C5 C8 H8A 111.1 . . ? C7 C8 H8B 111.1 . . ? C5 C8 H8B 111.1 . . ? H8A C8 H8B 109.1 . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C14 N3 C22 108.67(17) . . ? C14 N3 C18 110.98(17) . . ? C22 N3 C18 108.78(17) . . ? C14 N3 C10 108.56(17) . . ? C22 N3 C10 111.11(17) . . ? C18 N3 C10 108.76(17) . . ? C11 C10 N3 115.15(18) . . ? C11 C10 H10A 108.5 . . ? N3 C10 H10A 108.5 . . ? C11 C10 H10B 108.5 . . ? N3 C10 H10B 108.5 . . ? H10A C10 H10B 107.5 . . ? C10 C11 C12 110.5(2) . . ? C10 C11 H11A 109.5 . . ? C12 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? C13 C12 C11 111.1(2) . . ? C13 C12 H12A 109.4 . . ? C11 C12 H12A 109.4 . . ? C13 C12 H12B 109.4 . . ? C11 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N3 C14 C15 115.72(18) . . ? N3 C14 H14A 108.3 . . ? C15 C14 H14A 108.3 . . ? N3 C14 H14B 108.3 . . ? C15 C14 H14B 108.3 . . ? H14A C14 H14B 107.4 . . ? C14 C15 C16 109.8(2) . . ? C14 C15 H15A 109.7 . . ? C16 C15 H15A 109.7 . . ? C14 C15 H15B 109.7 . . ? C16 C15 H15B 109.7 . . ? H15A C15 H15B 108.2 . . ? C17 C16 C15 112.5(2) . . ? C17 C16 H16A 109.1 . . ? C15 C16 H16A 109.1 . . ? C17 C16 H16B 109.1 . . ? C15 C16 H16B 109.1 . . ? H16A C16 H16B 107.8 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 N3 115.12(19) . . ? C19 C18 H18A 108.5 . . ? N3 C18 H18A 108.5 . . ? C19 C18 H18B 108.5 . . ? N3 C18 H18B 108.5 . . ? H18A C18 H18B 107.5 . . ? C18 C19 C20 109.7(2) . . ? C18 C19 H19A 109.7 . . ? C20 C19 H19A 109.7 . . ? C18 C19 H19B 109.7 . . ? C20 C19 H19B 109.7 . . ? H19A C19 H19B 108.2 . . ? C21 C20 C19 111.9(2) . . ? C21 C20 H20A 109.2 . . ? C19 C20 H20A 109.2 . . ? C21 C20 H20B 109.2 . . ? C19 C20 H20B 109.2 . . ? H20A C20 H20B 107.9 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N3 C22 C23 115.46(18) . . ? N3 C22 H22A 108.4 . . ? C23 C22 H22A 108.4 . . ? N3 C22 H22B 108.4 . . ? C23 C22 H22B 108.4 . . ? H22A C22 H22B 107.5 . . ? C22 C23 C24 109.82(19) . . ? C22 C23 H23A 109.7 . . ? C24 C23 H23A 109.7 . . ? C22 C23 H23B 109.7 . . ? C24 C23 H23B 109.7 . . ? H23A C23 H23B 108.2 . . ? C25 C24 C23 112.0(2) . . ? C25 C24 H24A 109.2 . . ? C23 C24 H24A 109.2 . . ? C25 C24 H24B 109.2 . . ? C23 C24 H24B 109.2 . . ? H24A C24 H24B 107.9 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? O3 S1 O1 116.03(13) . . ? O3 S1 O2 114.77(13) . . ? O1 S1 O2 114.05(12) . . ? O3 S1 C1S 103.05(14) . . ? O1 S1 C1S 103.02(13) . . ? O2 S1 C1S 103.52(13) . . ? F3 C1S F1 107.2(2) . . ? F3 C1S F2 108.5(2) . . ? F1 C1S F2 106.1(3) . . ? F3 C1S S1 111.9(2) . . ? F1 C1S S1 112.1(2) . . ? F2 C1S S1 110.81(19) . . ? O4 S2 O6 114.22(13) . . ? O4 S2 O5 114.72(11) . . ? O6 S2 O5 115.49(13) . . ? O4 S2 C2S 103.24(13) . . ? O6 S2 C2S 103.11(13) . . ? O5 S2 C2S 103.79(13) . . ? F6 C2S F4 108.2(2) . . ? F6 C2S F5 107.0(2) . . ? F4 C2S F5 107.5(2) . . ? F6 C2S S2 112.1(2) . . ? F4 C2S S2 110.74(19) . . ? F5 C2S S2 111.1(2) . . ? _diffrn_measured_fraction_theta_max 0.820 _diffrn_reflns_theta_full 28.93 _diffrn_measured_fraction_theta_full 0.820 _refine_diff_density_max 1.781 _refine_diff_density_min -0.414 _refine_diff_density_rms 0.073