# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2008 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Robin Rogers' _publ_contact_author_email R.ROGERS@QUB.AC.UK _publ_section_title ; Ionic Liquids with Dual Biological Function: Sweet and Anti-microbial, Hydrophobic Quaternary Ammonium-based Salts ; loop_ _publ_author_name 'Robin D Rogers' 'Teresa Adamska' 'Scott Griffin' 'Whitney Hough-Troutman' ; J.Jodynis-Liebert ; 'Ilona Mirska' 'Jan Nawrot' 'Juliusz Pernak' 'W. Matthew Reichert' 'Marcin Smiglak' ; M.Stasiewicz ; # Attachment '[1-_OctOMe_-3-OH-Py][Sac].cif' data_s1 _database_code_depnum_ccdc_archive 'CCDC 687477' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H28 N2 O5 S' _chemical_formula_weight 420.51 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 8.1626(15) _cell_length_b 8.7141(16) _cell_length_c 16.756(3) _cell_angle_alpha 81.872(3) _cell_angle_beta 80.780(3) _cell_angle_gamma 62.850(3) _cell_volume 1043.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 970 _cell_measurement_theta_min 2.88 _cell_measurement_theta_max 23.27 _exptl_crystal_description Rectangular _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.338 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.190 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9010 _exptl_absorpt_correction_T_max 0.9775 _exptl_absorpt_process_details '(SADABS, Sheldrick 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4561 _diffrn_reflns_av_R_equivalents 0.0170 _diffrn_reflns_av_sigmaI/netI 0.0318 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 23.27 _reflns_number_total 2969 _reflns_number_gt 2514 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0482P)^2^+0.4846P] 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 refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0065(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2969 _refine_ls_number_parameters 375 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0472 _refine_ls_R_factor_gt 0.0362 _refine_ls_wR_factor_ref 0.0937 _refine_ls_wR_factor_gt 0.0871 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.007 _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 S1 S 0.39183(7) 0.27884(7) 0.35697(3) 0.02629(19) Uani 1 1 d . . . O1 O 0.8208(2) 0.1934(2) 0.22377(9) 0.0393(4) Uani 1 1 d . . . O2 O 0.2627(2) 0.4506(2) 0.37834(10) 0.0376(4) Uani 1 1 d . . . O3 O 0.3871(2) 0.1435(2) 0.41670(9) 0.0322(4) Uani 1 1 d . . . O4 O -0.2239(2) 0.82226(19) 0.31650(9) 0.0299(4) Uani 1 1 d . . . O5 O 0.2161(2) 0.6352(2) 0.59064(9) 0.0388(4) Uani 1 1 d . . . H5O H 0.289(4) 0.669(3) 0.6132(16) 0.047(8) Uiso 1 1 d . . . N1 N 0.6001(2) 0.2580(2) 0.33374(11) 0.0293(4) Uani 1 1 d . . . N2 N -0.0454(2) 0.8023(2) 0.42162(10) 0.0235(4) Uani 1 1 d . . . C1 C -0.9026(4) 0.6724(5) -0.00403(18) 0.0485(7) Uani 1 1 d . . . H1B H -0.882(4) 0.560(4) -0.0241(19) 0.070(9) Uiso 1 1 d . . . H1A H -0.885(4) 0.750(4) -0.048(2) 0.072(10) Uiso 1 1 d . . . H1C H -1.030(4) 0.720(4) 0.0163(18) 0.058(9) Uiso 1 1 d . . . C2 C -0.8238(3) 0.8024(3) 0.10088(15) 0.0340(6) Uani 1 1 d . . . H2B H -0.797(3) 0.887(3) 0.0602(15) 0.038(6) Uiso 1 1 d . . . H2A H -0.956(4) 0.863(3) 0.1219(15) 0.047(7) Uiso 1 1 d . . . C3 C -0.7814(4) 0.6399(3) 0.06239(16) 0.0392(6) Uani 1 1 d . . . H3B H -0.799(3) 0.558(3) 0.1057(16) 0.040(7) Uiso 1 1 d . . . H3A H -0.648(4) 0.587(4) 0.0419(17) 0.057(8) Uiso 1 1 d . . . C4 C 0.1843(3) 0.8991(3) 0.39872(13) 0.0299(5) Uani 1 1 d . . . H4 H 0.238(3) 0.966(3) 0.3662(15) 0.039(7) Uiso 1 1 d . . . C5 C -0.4161(3) 0.7089(3) 0.22445(14) 0.0324(6) Uani 1 1 d . . . H5A H -0.423(3) 0.618(3) 0.2652(15) 0.039(7) Uiso 1 1 d . . . H5B H -0.492(3) 0.819(3) 0.2476(15) 0.037(7) Uiso 1 1 d . . . C6 C 0.3864(3) 0.1731(3) 0.10467(14) 0.0353(6) Uani 1 1 d . . . H6 H 0.392(4) 0.152(3) 0.0514(17) 0.050(8) Uiso 1 1 d . . . C7 C -0.5085(3) 0.7148(4) 0.15156(14) 0.0322(5) Uani 1 1 d . . . H7B H -0.452(3) 0.601(3) 0.1332(15) 0.039(7) Uiso 1 1 d . . . H7A H -0.492(3) 0.799(3) 0.1103(15) 0.041(7) Uiso 1 1 d . . . C8 C 0.5382(3) 0.1740(3) 0.13157(14) 0.0327(6) Uani 1 1 d . . . H8 H 0.650(4) 0.153(3) 0.0967(16) 0.043(7) Uiso 1 1 d . . . C9 C -0.7161(3) 0.7716(4) 0.17285(15) 0.0335(6) Uani 1 1 d . . . H9A H -0.732(3) 0.684(3) 0.2087(15) 0.039(7) Uiso 1 1 d . . . H9B H -0.767(3) 0.876(3) 0.2023(15) 0.038(7) Uiso 1 1 d . . . C10 C 0.6650(3) 0.2188(3) 0.25500(13) 0.0279(5) Uani 1 1 d . . . C11 C -0.2187(3) 0.8050(3) 0.39889(13) 0.0295(5) Uani 1 1 d . . . H11C H -0.219(3) 0.696(3) 0.4234(13) 0.024(5) Uiso 1 1 d . . . H11B H -0.316(3) 0.904(3) 0.4209(13) 0.027(6) Uiso 1 1 d . . . C12 C 0.0348(3) 0.8926(3) 0.37403(14) 0.0277(5) Uani 1 1 d . . . H12 H -0.020(3) 0.952(3) 0.3264(15) 0.034(6) Uiso 1 1 d . . . C13 C 0.3603(3) 0.2415(3) 0.26119(12) 0.0236(5) Uani 1 1 d . . . C14 C 0.2094(3) 0.2390(3) 0.23514(14) 0.0272(5) Uani 1 1 d . . . H14 H 0.107(3) 0.257(3) 0.2705(14) 0.029(6) Uiso 1 1 d . . . C15 C 0.5232(3) 0.2094(3) 0.21106(12) 0.0264(5) Uani 1 1 d . . . C16 C 0.1646(3) 0.7230(3) 0.51916(13) 0.0260(5) Uani 1 1 d . . . C17 C 0.2244(3) 0.2046(3) 0.15548(14) 0.0325(6) Uani 1 1 d . . . H17 H 0.118(3) 0.200(3) 0.1352(14) 0.033(6) Uiso 1 1 d . . . C18 C -0.1220(3) 0.6616(3) 0.27710(14) 0.0301(5) Uani 1 1 d . . . H18A H -0.127(3) 0.568(3) 0.3159(13) 0.026(6) Uiso 1 1 d . . . H18B H 0.014(4) 0.644(3) 0.2627(15) 0.042(7) Uiso 1 1 d . . . C19 C -0.2148(3) 0.6771(4) 0.20356(14) 0.0318(5) Uani 1 1 d . . . H19B H -0.210(3) 0.770(3) 0.1656(15) 0.036(6) Uiso 1 1 d . . . H19A H -0.146(4) 0.575(4) 0.1785(16) 0.045(7) Uiso 1 1 d . . . C20 C 0.2509(3) 0.8150(3) 0.47138(13) 0.0291(5) Uani 1 1 d . . . H20 H 0.352(3) 0.821(3) 0.4878(14) 0.032(6) Uiso 1 1 d . . . C21 C 0.0165(3) 0.7182(3) 0.49184(13) 0.0242(5) Uani 1 1 d . . . H21 H -0.045(3) 0.656(3) 0.5212(12) 0.019(5) 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 0.0212(3) 0.0313(3) 0.0237(3) -0.0064(2) -0.0018(2) -0.0084(2) O1 0.0259(9) 0.0583(11) 0.0334(9) -0.0013(8) 0.0017(7) -0.0205(8) O2 0.0317(9) 0.0332(9) 0.0403(10) -0.0157(7) -0.0035(7) -0.0043(7) O3 0.0270(9) 0.0402(9) 0.0241(8) -0.0006(7) 0.0006(7) -0.0118(7) O4 0.0314(9) 0.0309(8) 0.0254(8) -0.0032(7) -0.0079(7) -0.0103(7) O5 0.0475(11) 0.0524(11) 0.0309(9) 0.0101(8) -0.0177(8) -0.0339(9) N1 0.0241(10) 0.0382(11) 0.0264(10) -0.0039(8) -0.0034(8) -0.0138(9) N2 0.0200(9) 0.0257(9) 0.0217(10) -0.0060(8) -0.0010(8) -0.0069(8) C1 0.0484(19) 0.074(2) 0.0376(16) -0.0056(16) -0.0065(14) -0.0391(17) C2 0.0278(14) 0.0380(14) 0.0359(14) -0.0025(11) -0.0060(11) -0.0138(12) C3 0.0377(16) 0.0463(15) 0.0380(15) -0.0045(13) -0.0080(12) -0.0208(13) C4 0.0334(13) 0.0325(13) 0.0255(12) -0.0044(10) 0.0030(10) -0.0175(11) C5 0.0303(13) 0.0412(15) 0.0282(13) -0.0044(12) -0.0020(10) -0.0180(12) C6 0.0448(16) 0.0382(14) 0.0224(13) -0.0041(11) -0.0085(11) -0.0160(12) C7 0.0306(13) 0.0388(15) 0.0293(13) -0.0069(11) -0.0032(10) -0.0162(12) C8 0.0330(14) 0.0363(13) 0.0243(12) -0.0037(10) 0.0006(11) -0.0123(11) C9 0.0303(13) 0.0400(15) 0.0329(14) -0.0058(12) -0.0020(11) -0.0174(12) C10 0.0243(13) 0.0299(12) 0.0267(12) 0.0006(9) -0.0018(10) -0.0106(10) C11 0.0229(13) 0.0363(14) 0.0257(13) -0.0069(11) -0.0029(10) -0.0087(12) C12 0.0272(12) 0.0268(12) 0.0241(12) -0.0025(10) -0.0022(10) -0.0077(10) C13 0.0242(12) 0.0211(11) 0.0217(11) -0.0018(9) -0.0021(9) -0.0068(9) C14 0.0230(12) 0.0267(12) 0.0291(13) -0.0013(10) -0.0028(10) -0.0089(10) C15 0.0270(12) 0.0264(12) 0.0232(12) -0.0010(9) -0.0027(9) -0.0099(10) C16 0.0271(12) 0.0267(12) 0.0237(12) -0.0038(9) -0.0033(9) -0.0109(10) C17 0.0350(14) 0.0314(13) 0.0334(13) -0.0007(10) -0.0138(11) -0.0139(11) C18 0.0259(13) 0.0305(13) 0.0320(13) -0.0047(11) -0.0047(10) -0.0097(11) C19 0.0266(13) 0.0384(14) 0.0287(13) -0.0077(12) -0.0011(10) -0.0123(11) C20 0.0280(13) 0.0352(13) 0.0282(13) -0.0075(10) -0.0027(10) -0.0163(11) C21 0.0236(12) 0.0251(11) 0.0223(11) -0.0051(9) 0.0007(9) -0.0097(10) _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 O2 1.4389(16) . ? S1 O3 1.4452(16) . ? S1 N1 1.6129(19) . ? S1 C13 1.762(2) . ? O1 C10 1.226(3) . ? O4 C11 1.373(3) . ? O4 C18 1.453(3) . ? O5 C16 1.343(3) . ? N1 C10 1.370(3) . ? N2 C21 1.336(3) . ? N2 C12 1.345(3) . ? N2 C11 1.512(3) . ? C1 C3 1.518(4) . ? C2 C3 1.510(4) . ? C2 C9 1.527(3) . ? C4 C12 1.376(3) . ? C4 C20 1.383(3) . ? C5 C7 1.518(3) . ? C5 C19 1.525(3) . ? C6 C17 1.387(3) . ? C6 C8 1.388(3) . ? C7 C9 1.529(3) . ? C8 C15 1.383(3) . ? C10 C15 1.505(3) . ? C13 C14 1.381(3) . ? C13 C15 1.386(3) . ? C14 C17 1.383(3) . ? C16 C21 1.379(3) . ? C16 C20 1.390(3) . ? C18 C19 1.506(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 O2 S1 O3 113.96(10) . . ? O2 S1 N1 112.35(10) . . ? O3 S1 N1 111.07(9) . . ? O2 S1 C13 111.04(9) . . ? O3 S1 C13 110.18(10) . . ? N1 S1 C13 97.01(10) . . ? C11 O4 C18 114.59(17) . . ? C10 N1 S1 111.99(15) . . ? C21 N2 C12 121.88(19) . . ? C21 N2 C11 118.23(18) . . ? C12 N2 C11 119.75(18) . . ? C3 C2 C9 114.2(2) . . ? C2 C3 C1 113.0(2) . . ? C12 C4 C20 120.7(2) . . ? C7 C5 C19 113.6(2) . . ? C17 C6 C8 121.7(2) . . ? C5 C7 C9 111.8(2) . . ? C15 C8 C6 118.0(2) . . ? C2 C9 C7 115.2(2) . . ? O1 C10 N1 124.1(2) . . ? O1 C10 C15 123.7(2) . . ? N1 C10 C15 112.23(18) . . ? O4 C11 N2 112.50(18) . . ? N2 C12 C4 118.9(2) . . ? C14 C13 C15 122.5(2) . . ? C14 C13 S1 130.17(17) . . ? C15 C13 S1 107.33(15) . . ? C13 C14 C17 117.5(2) . . ? C8 C15 C13 119.9(2) . . ? C8 C15 C10 128.7(2) . . ? C13 C15 C10 111.42(18) . . ? O5 C16 C21 116.64(19) . . ? O5 C16 C20 124.8(2) . . ? C21 C16 C20 118.6(2) . . ? C14 C17 C6 120.5(2) . . ? O4 C18 C19 108.00(18) . . ? C18 C19 C5 112.9(2) . . ? C4 C20 C16 118.9(2) . . ? N2 C21 C16 121.0(2) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 23.27 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.180 _refine_diff_density_min -0.337 _refine_diff_density_rms 0.042 # Attachment 'B813213P_[HEX][Ace] Revised 08-07-08.cif' data_w1 _database_code_depnum_ccdc_archive 'CCDC 687478' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '1-hexadecylyridinium acesulfame' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H42 N2 O4 S' _chemical_formula_weight 466.67 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 7.921(3) _cell_length_b 13.374(5) _cell_length_c 25.689(10) _cell_angle_alpha 76.755(7) _cell_angle_beta 82.225(7) _cell_angle_gamma 89.260(7) _cell_volume 2624.2(17) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 900 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 23.21 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 1.42 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.181 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 0.155 _exptl_absorpt_correction_type sphere _exptl_absorpt_correction_T_min 0.7162 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11913 _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_sigmaI/netI 0.0427 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 23.32 _reflns_number_total 7459 _reflns_number_gt 5755 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0871P)^2^+0.5202P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7459 _refine_ls_number_parameters 913 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0641 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1411 _refine_ls_wR_factor_gt 0.1208 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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 0.8308(3) 0.54899(15) -0.05656(8) 0.0319(5) Uani 1 1 d . . . N2 N 1.3311(3) 0.24520(15) -0.10443(9) 0.0334(5) Uani 1 1 d . . . S1 S 1.52717(9) 0.25036(5) -0.12268(3) 0.0361(2) Uani 1 1 d . . . O1 O 1.5909(3) 0.15038(14) -0.12417(9) 0.0542(6) Uani 1 1 d . . . O2 O 1.6188(2) 0.30880(14) -0.09500(8) 0.0416(5) Uani 1 1 d . . . O3 O 1.5553(2) 0.31382(14) -0.18556(7) 0.0405(5) Uani 1 1 d . . . O4 O 1.0891(2) 0.33614(14) -0.10062(7) 0.0406(5) Uani 1 1 d . . . C2 C 0.8369(4) 0.4491(2) -0.03123(11) 0.0342(6) Uani 1 1 d . . . H2C H 0.904(3) 0.410(2) -0.0509(11) 0.038(8) Uiso 1 1 d . . . C3 C 0.7550(4) 0.4146(2) 0.01974(11) 0.0370(7) Uani 1 1 d . . . H3A H 0.753(3) 0.342(2) 0.0368(10) 0.035(7) Uiso 1 1 d . . . C4 C 0.6624(4) 0.4811(2) 0.04550(11) 0.0385(7) Uani 1 1 d . . . H4A H 0.600(4) 0.462(2) 0.0809(12) 0.041(8) Uiso 1 1 d . . . C5 C 0.6551(4) 0.5824(2) 0.01876(12) 0.0405(7) Uani 1 1 d . . . H5A H 0.592(4) 0.629(2) 0.0339(11) 0.044(8) Uiso 1 1 d . . . C6 C 0.7393(4) 0.6151(2) -0.03234(12) 0.0380(7) Uani 1 1 d . . . H6A H 0.743(4) 0.681(2) -0.0542(12) 0.049(9) Uiso 1 1 d . . . C7 C 0.9259(4) 0.5856(3) -0.11147(11) 0.0422(7) Uani 1 1 d . . . H7A H 1.033(4) 0.540(2) -0.1108(12) 0.059(9) Uiso 1 1 d . . . H7B H 0.942(4) 0.651(3) -0.1137(12) 0.055(10) Uiso 1 1 d . . . C8 C 0.8285(4) 0.5694(2) -0.15541(11) 0.0351(6) Uani 1 1 d . . . H8A H 0.722(4) 0.594(2) -0.1506(10) 0.032(7) Uiso 1 1 d . . . H8B H 0.802(4) 0.496(2) -0.1520(11) 0.045(8) Uiso 1 1 d . . . C9 C 0.9261(4) 0.6201(2) -0.21093(11) 0.0346(6) Uani 1 1 d . . . H9A H 1.047(4) 0.5933(19) -0.2132(10) 0.033(7) Uiso 1 1 d . . . H9B H 0.871(4) 0.592(2) -0.2400(12) 0.054(8) Uiso 1 1 d . . . C10 C 0.9193(4) 0.7368(2) -0.22460(11) 0.0335(6) Uani 1 1 d . . . H10A H 0.954(4) 0.762(2) -0.1936(12) 0.050(8) Uiso 1 1 d . . . H10B H 0.802(4) 0.754(2) -0.2267(11) 0.042(8) Uiso 1 1 d . . . C11 C 1.0334(4) 0.7863(2) -0.27678(11) 0.0330(6) Uani 1 1 d . . . H11A H 1.147(4) 0.759(2) -0.2732(10) 0.034(7) Uiso 1 1 d . . . H11B H 0.993(3) 0.763(2) -0.3089(11) 0.043(8) Uiso 1 1 d . . . C12 C 1.0327(4) 0.9031(2) -0.28848(11) 0.0349(6) Uani 1 1 d . . . H12A H 1.080(4) 0.929(2) -0.2605(12) 0.047(8) Uiso 1 1 d . . . H12B H 0.902(4) 0.925(2) -0.2868(11) 0.050(8) Uiso 1 1 d . . . C13 C 1.1300(4) 0.9559(2) -0.34303(11) 0.0367(7) Uani 1 1 d . . . H13A H 1.243(4) 0.937(2) -0.3446(11) 0.045(8) Uiso 1 1 d . . . H13B H 1.089(4) 0.926(2) -0.3724(12) 0.051(8) Uiso 1 1 d . . . C14 C 1.1158(4) 1.0726(2) -0.35578(11) 0.0359(6) Uani 1 1 d . . . H14A H 0.986(4) 1.092(2) -0.3508(11) 0.047(8) Uiso 1 1 d . . . H14B H 1.160(3) 1.099(2) -0.3274(11) 0.034(7) Uiso 1 1 d . . . C15 C 1.2010(4) 1.1259(2) -0.41160(12) 0.0380(7) Uani 1 1 d . . . H15A H 1.154(4) 1.097(2) -0.4384(11) 0.042(8) Uiso 1 1 d . . . H15B H 1.319(4) 1.108(2) -0.4160(12) 0.051(9) Uiso 1 1 d . . . C16 C 1.1811(4) 1.2422(2) -0.42372(12) 0.0376(7) Uani 1 1 d . . . H16A H 1.061(4) 1.254(2) -0.4194(12) 0.054(9) Uiso 1 1 d . . . H16B H 1.226(4) 1.270(2) -0.3940(12) 0.048(8) Uiso 1 1 d . . . C17 C 1.2641(4) 1.2965(2) -0.47985(12) 0.0393(7) Uani 1 1 d . . . H17A H 1.215(4) 1.270(2) -0.5072(12) 0.047(8) Uiso 1 1 d . . . H17B H 1.384(4) 1.278(2) -0.4842(11) 0.043(8) Uiso 1 1 d . . . C18 C 1.2435(4) 1.4130(2) -0.49218(12) 0.0382(7) Uani 1 1 d . . . H18A H 1.118(4) 1.433(2) -0.4868(11) 0.046(8) Uiso 1 1 d . . . H18B H 1.288(4) 1.443(2) -0.4645(13) 0.054(9) Uiso 1 1 d . . . C19 C 1.3265(4) 1.4668(2) -0.54837(12) 0.0392(7) Uani 1 1 d . . . H19A H 1.281(4) 1.436(2) -0.5756(12) 0.052(9) Uiso 1 1 d . . . H19B H 1.445(4) 1.447(2) -0.5508(11) 0.046(8) Uiso 1 1 d . . . C20 C 1.3105(4) 1.5830(2) -0.56155(12) 0.0388(7) Uani 1 1 d . . . H20A H 1.182(5) 1.601(2) -0.5586(12) 0.065(10) Uiso 1 1 d . . . H20B H 1.350(4) 1.614(2) -0.5354(13) 0.053(9) Uiso 1 1 d . . . C21 C 1.3948(5) 1.6346(2) -0.61754(13) 0.0492(8) Uani 1 1 d . . . H21A H 1.510(4) 1.617(2) -0.6209(12) 0.052(9) Uiso 1 1 d . . . H21B H 1.347(4) 1.607(2) -0.6459(13) 0.054(9) Uiso 1 1 d . . . C22 C 1.3825(6) 1.7503(3) -0.63163(18) 0.0607(10) Uani 1 1 d . . . H22A H 1.436(5) 1.775(3) -0.6716(18) 0.095(13) Uiso 1 1 d . . . H22B H 1.426(5) 1.776(3) -0.6095(16) 0.073(14) Uiso 1 1 d . . . H22C H 1.253(6) 1.776(3) -0.6350(17) 0.106(15) Uiso 1 1 d . . . C23 C 1.4597(3) 0.4018(2) -0.19663(11) 0.0361(7) Uani 1 1 d . . . C24 C 1.3168(4) 0.4123(2) -0.16595(11) 0.0339(6) Uani 1 1 d . . . H24A H 1.255(3) 0.467(2) -0.1742(10) 0.030(7) Uiso 1 1 d . . . C25 C 1.2378(3) 0.33039(19) -0.12110(10) 0.0310(6) Uani 1 1 d . . . C26 C 1.5375(5) 0.4767(3) -0.24601(14) 0.0530(9) Uani 1 1 d . . . H26A H 1.478(5) 0.526(3) -0.2514(14) 0.059(13) Uiso 1 1 d . . . H26B H 1.530(5) 0.445(3) -0.2777(17) 0.091(13) Uiso 1 1 d . . . H26C H 1.666(6) 0.480(3) -0.2454(17) 0.111(15) Uiso 1 1 d . . . N1A N 0.9225(3) 1.00636(15) 0.07716(8) 0.0298(5) Uani 1 1 d . . . N2A N 1.5002(3) 1.24701(15) 0.12413(9) 0.0354(5) Uani 1 1 d . . . S1A S 1.64385(9) 1.23985(5) 0.16088(3) 0.0351(2) Uani 1 1 d . . . O1A O 1.6588(3) 1.33345(14) 0.17781(8) 0.0520(6) Uani 1 1 d . . . O2A O 1.7984(2) 1.19967(14) 0.13926(8) 0.0432(5) Uani 1 1 d . . . O3A O 1.5770(2) 1.15601(14) 0.21706(7) 0.0413(5) Uani 1 1 d . . . O4A O 1.3317(3) 1.15657(14) 0.08688(8) 0.0488(5) Uani 1 1 d . . . C2A C 1.0324(4) 1.0796(2) 0.04651(11) 0.0357(7) Uani 1 1 d . . . H2B H 1.139(4) 1.072(2) 0.0571(12) 0.050(9) Uiso 1 1 d . . . C3A C 0.9813(4) 1.1538(2) 0.00648(11) 0.0431(7) Uani 1 1 d . . . H3B H 1.063(5) 1.207(3) -0.0173(14) 0.081(11) Uiso 1 1 d . . . C4A C 0.8148(5) 1.1554(2) -0.00293(12) 0.0472(8) Uani 1 1 d . . . H4B H 0.771(4) 1.203(3) -0.0315(13) 0.061(9) Uiso 1 1 d . . . C5A C 0.7015(4) 1.0819(2) 0.02985(13) 0.0475(8) Uani 1 1 d . . . H5B H 0.585(5) 1.084(3) 0.0262(13) 0.066(10) Uiso 1 1 d . . . C6A C 0.7570(4) 1.0080(2) 0.06964(12) 0.0395(7) Uani 1 1 d . . . H6B H 0.686(4) 0.950(2) 0.0965(12) 0.058(9) Uiso 1 1 d . . . C7A C 0.9856(4) 0.9249(2) 0.11935(11) 0.0401(7) Uani 1 1 d . . . H7D H 1.106(4) 0.909(2) 0.1065(12) 0.061(10) Uiso 1 1 d . . . H7C H 0.927(4) 0.862(3) 0.1222(12) 0.060(9) Uiso 1 1 d . . . C8A C 0.9720(4) 0.9538(2) 0.17272(11) 0.0356(6) Uani 1 1 d . . . H8D H 0.853(3) 0.9663(18) 0.1829(9) 0.028(7) Uiso 1 1 d . . . H8C H 1.037(4) 1.014(2) 0.1691(11) 0.044(8) Uiso 1 1 d . . . C9A C 1.0424(4) 0.8706(2) 0.21486(12) 0.0352(7) Uani 1 1 d . . . H9D H 1.165(4) 0.851(2) 0.2008(10) 0.040(7) Uiso 1 1 d . . . H9C H 1.051(3) 0.890(2) 0.2441(11) 0.032(7) Uiso 1 1 d . . . C10A C 0.9353(4) 0.7721(2) 0.23310(12) 0.0384(7) Uani 1 1 d . . . H10D H 0.930(3) 0.742(2) 0.2042(11) 0.033(7) Uiso 1 1 d . . . H10C H 0.820(4) 0.784(2) 0.2465(11) 0.042(8) Uiso 1 1 d . . . C11A C 1.0042(4) 0.6928(2) 0.27716(12) 0.0367(7) Uani 1 1 d . . . H11D H 1.015(4) 0.718(2) 0.3049(12) 0.040(8) Uiso 1 1 d . . . H11C H 1.122(4) 0.674(2) 0.2634(11) 0.048(8) Uiso 1 1 d . . . C12A C 0.8925(4) 0.5965(2) 0.29786(12) 0.0388(7) Uani 1 1 d . . . H12D H 0.889(4) 0.567(3) 0.2702(14) 0.062(10) Uiso 1 1 d . . . H12C H 0.773(4) 0.6167(19) 0.3086(10) 0.030(7) Uiso 1 1 d . . . C13A C 0.9543(4) 0.5185(2) 0.34421(12) 0.0380(7) Uani 1 1 d . . . H13D H 1.070(4) 0.494(2) 0.3317(11) 0.041(8) Uiso 1 1 d . . . H13C H 0.966(4) 0.552(2) 0.3696(13) 0.051(9) Uiso 1 1 d . . . C14A C 0.8357(4) 0.4259(2) 0.36695(12) 0.0383(7) Uani 1 1 d . . . H14D H 0.824(3) 0.393(2) 0.3377(11) 0.037(7) Uiso 1 1 d . . . H14C H 0.727(5) 0.453(3) 0.3777(13) 0.063(10) Uiso 1 1 d . . . C15A C 0.8944(4) 0.3502(2) 0.41453(12) 0.0398(7) Uani 1 1 d . . . H15D H 1.011(4) 0.325(2) 0.4020(10) 0.037(7) Uiso 1 1 d . . . H15C H 0.912(4) 0.384(2) 0.4421(13) 0.054(9) Uiso 1 1 d . . . C16A C 0.7758(4) 0.2574(2) 0.43742(12) 0.0376(7) Uani 1 1 d . . . H16D H 0.770(3) 0.221(2) 0.4086(11) 0.040(7) Uiso 1 1 d . . . H16C H 0.660(4) 0.282(2) 0.4483(12) 0.052(9) Uiso 1 1 d . . . C17A C 0.8315(4) 0.1824(2) 0.48556(13) 0.0406(7) Uani 1 1 d . . . H17D H 0.844(4) 0.212(2) 0.5153(13) 0.051(9) Uiso 1 1 d . . . H17C H 0.948(4) 0.160(2) 0.4748(11) 0.041(8) Uiso 1 1 d . . . C18A C 0.7126(4) 0.0889(2) 0.50813(12) 0.0384(7) Uani 1 1 d . . . H18D H 0.596(4) 0.113(2) 0.5198(11) 0.041(8) Uiso 1 1 d . . . H18C H 0.701(4) 0.051(2) 0.4802(12) 0.053(9) Uiso 1 1 d . . . C19A C 0.7673(4) 0.0146(2) 0.55629(13) 0.0424(7) Uani 1 1 d . . . H19D H 0.776(4) 0.048(2) 0.5836(12) 0.046(8) Uiso 1 1 d . . . H19C H 0.888(4) -0.006(2) 0.5434(12) 0.056(9) Uiso 1 1 d . . . C20A C 0.6498(4) -0.0793(2) 0.57934(13) 0.0399(7) Uani 1 1 d . . . H20C H 0.542(4) -0.055(2) 0.5898(12) 0.058(10) Uiso 1 1 d . . . H20D H 0.645(4) -0.115(3) 0.5515(13) 0.059(10) Uiso 1 1 d . . . C21A C 0.7103(5) -0.1533(2) 0.62616(14) 0.0480(8) Uani 1 1 d . . . H21C H 0.728(4) -0.119(3) 0.6549(14) 0.070(11) Uiso 1 1 d . . . H21D H 0.829(5) -0.171(3) 0.6121(14) 0.076(11) Uiso 1 1 d . . . C22A C 0.5952(6) -0.2475(3) 0.65025(17) 0.0607(10) Uani 1 1 d . . . H22D H 0.647(4) -0.295(3) 0.6759(14) 0.060(10) Uiso 1 1 d . . . H22E H 0.591(5) -0.293(3) 0.6224(17) 0.097(14) Uiso 1 1 d . . . H22F H 0.489(6) -0.229(3) 0.6624(17) 0.097(16) Uiso 1 1 d . . . C23A C 1.4988(3) 1.0682(2) 0.21044(12) 0.0393(7) Uani 1 1 d . . . C24A C 1.4309(4) 1.0673(2) 0.16659(12) 0.0383(7) Uani 1 1 d . . . H24B H 1.381(4) 1.006(2) 0.1632(11) 0.042(8) Uiso 1 1 d . . . C25A C 1.4200(3) 1.15832(19) 0.12300(11) 0.0356(6) Uani 1 1 d . . . C26A C 1.4970(5) 0.9822(3) 0.25888(16) 0.0572(9) Uani 1 1 d . . . H26F H 1.427(5) 0.913(3) 0.2488(16) 0.099(13) Uiso 1 1 d . . . H26E H 1.437(5) 0.995(3) 0.2891(15) 0.065(11) Uiso 1 1 d . . . H26D H 1.604(4) 0.964(2) 0.2654(12) 0.052(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 N1 0.0326(12) 0.0279(12) 0.0330(12) -0.0020(10) -0.0052(9) -0.0100(10) N2 0.0292(12) 0.0254(12) 0.0421(13) -0.0033(10) 0.0011(10) -0.0049(9) S1 0.0329(4) 0.0284(4) 0.0451(4) -0.0075(3) 0.0002(3) -0.0019(3) O1 0.0472(13) 0.0337(11) 0.0803(15) -0.0167(11) 0.0022(11) 0.0068(9) O2 0.0364(11) 0.0411(11) 0.0480(11) -0.0094(9) -0.0088(9) -0.0064(9) O3 0.0376(11) 0.0443(12) 0.0383(11) -0.0123(9) 0.0050(8) -0.0040(9) O4 0.0330(11) 0.0387(11) 0.0453(11) -0.0049(9) 0.0034(9) -0.0019(8) C2 0.0385(16) 0.0262(15) 0.0367(16) -0.0059(13) -0.0025(13) -0.0041(12) C3 0.0429(17) 0.0284(15) 0.0352(16) -0.0005(13) 0.0000(13) -0.0098(13) C4 0.0375(16) 0.0454(18) 0.0326(16) -0.0100(14) -0.0017(13) -0.0084(13) C5 0.0420(17) 0.0409(17) 0.0464(19) -0.0219(15) -0.0124(14) 0.0028(14) C6 0.0446(17) 0.0283(16) 0.0437(18) -0.0060(14) -0.0179(14) -0.0049(13) C7 0.0445(19) 0.0417(19) 0.0337(16) 0.0053(14) -0.0038(13) -0.0161(15) C8 0.0362(18) 0.0297(16) 0.0357(16) -0.0013(12) -0.0013(12) -0.0115(13) C9 0.0448(18) 0.0263(14) 0.0305(15) -0.0021(11) -0.0042(13) -0.0074(13) C10 0.0374(17) 0.0283(15) 0.0308(15) -0.0001(12) -0.0015(12) -0.0047(12) C11 0.0355(16) 0.0281(14) 0.0310(15) 0.0009(12) -0.0024(12) -0.0021(12) C12 0.0425(18) 0.0283(15) 0.0307(15) -0.0011(12) -0.0025(12) -0.0095(13) C13 0.0393(18) 0.0278(15) 0.0374(16) 0.0002(12) 0.0021(13) -0.0051(13) C14 0.0423(18) 0.0280(14) 0.0322(15) 0.0012(12) -0.0001(13) -0.0074(13) C15 0.0408(18) 0.0277(15) 0.0402(17) -0.0012(13) 0.0022(14) -0.0055(13) C16 0.0392(18) 0.0307(15) 0.0380(17) -0.0002(12) -0.0008(13) -0.0041(13) C17 0.0426(19) 0.0278(15) 0.0403(17) 0.0020(13) 0.0033(14) -0.0046(13) C18 0.0407(18) 0.0301(15) 0.0388(17) -0.0008(13) 0.0010(13) -0.0050(13) C19 0.0414(18) 0.0292(15) 0.0412(17) -0.0006(13) 0.0023(14) -0.0043(13) C20 0.0424(18) 0.0306(15) 0.0385(17) -0.0006(13) -0.0001(13) -0.0079(13) C21 0.055(2) 0.0384(18) 0.0446(19) 0.0048(14) 0.0043(16) -0.0058(16) C22 0.070(3) 0.0387(19) 0.061(3) 0.0128(18) -0.007(2) -0.0076(18) C23 0.0392(17) 0.0345(16) 0.0344(15) -0.0080(12) -0.0029(13) -0.0122(13) C24 0.0391(17) 0.0242(14) 0.0366(16) -0.0023(12) -0.0066(13) -0.0033(13) C25 0.0335(16) 0.0276(14) 0.0323(14) -0.0079(11) -0.0033(12) -0.0043(12) C26 0.054(2) 0.056(2) 0.040(2) 0.0035(17) 0.0029(16) -0.020(2) N1A 0.0346(13) 0.0220(11) 0.0314(12) -0.0026(9) -0.0047(9) -0.0060(9) N2A 0.0410(13) 0.0237(11) 0.0393(13) 0.0003(10) -0.0097(10) -0.0073(10) S1A 0.0398(4) 0.0246(4) 0.0393(4) -0.0013(3) -0.0084(3) -0.0112(3) O1A 0.0687(15) 0.0300(11) 0.0616(13) -0.0125(10) -0.0191(11) -0.0149(10) O2A 0.0332(11) 0.0395(11) 0.0546(12) -0.0060(9) -0.0057(9) -0.0084(9) O3A 0.0519(12) 0.0352(11) 0.0332(10) 0.0010(8) -0.0072(9) -0.0112(9) O4A 0.0537(13) 0.0351(11) 0.0608(13) -0.0045(10) -0.0298(11) -0.0057(9) C2A 0.0352(17) 0.0340(16) 0.0388(16) -0.0104(13) -0.0039(13) -0.0108(13) C3A 0.067(2) 0.0274(15) 0.0328(16) -0.0036(13) -0.0028(15) -0.0122(15) C4A 0.076(2) 0.0310(16) 0.0380(18) -0.0079(14) -0.0197(16) 0.0098(16) C5A 0.0408(19) 0.051(2) 0.059(2) -0.0221(17) -0.0199(16) 0.0095(15) C6A 0.0345(16) 0.0373(16) 0.0472(17) -0.0118(14) -0.0024(13) -0.0073(13) C7A 0.052(2) 0.0296(16) 0.0381(16) -0.0031(13) -0.0130(14) 0.0026(14) C8A 0.0396(17) 0.0308(15) 0.0342(16) -0.0049(12) -0.0008(12) -0.0038(13) C9A 0.0457(18) 0.0306(15) 0.0273(15) -0.0021(12) -0.0051(13) -0.0059(13) C10A 0.0419(18) 0.0328(16) 0.0373(17) -0.0002(13) -0.0071(14) -0.0051(13) C11A 0.0427(18) 0.0318(15) 0.0325(16) -0.0007(13) -0.0044(13) -0.0067(13) C12A 0.0459(19) 0.0296(15) 0.0378(17) -0.0015(13) -0.0057(14) -0.0041(13) C13A 0.0469(19) 0.0290(15) 0.0363(17) -0.0032(13) -0.0064(14) -0.0052(13) C14A 0.0482(19) 0.0289(15) 0.0344(16) -0.0019(13) -0.0018(14) -0.0040(13) C15A 0.0489(19) 0.0287(15) 0.0389(17) -0.0025(13) -0.0050(14) -0.0036(13) C16A 0.0482(19) 0.0276(15) 0.0346(16) -0.0039(13) -0.0021(13) -0.0031(13) C17A 0.048(2) 0.0305(16) 0.0400(17) -0.0012(13) -0.0055(14) -0.0052(14) C18A 0.0461(19) 0.0270(15) 0.0395(17) -0.0028(13) -0.0043(13) -0.0082(13) C19A 0.052(2) 0.0289(15) 0.0441(18) -0.0024(14) -0.0097(15) -0.0096(14) C20A 0.0452(19) 0.0308(16) 0.0405(17) -0.0013(13) -0.0063(14) -0.0045(14) C21A 0.057(2) 0.0357(17) 0.0465(19) 0.0021(15) -0.0079(16) -0.0120(15) C22A 0.067(3) 0.042(2) 0.062(2) 0.0133(19) -0.012(2) -0.0150(18) C23A 0.0353(16) 0.0269(15) 0.0471(17) 0.0047(12) 0.0022(13) -0.0066(12) C24A 0.0384(16) 0.0230(14) 0.0511(18) -0.0010(13) -0.0097(14) -0.0087(12) C25A 0.0336(15) 0.0271(14) 0.0463(17) -0.0066(12) -0.0088(13) -0.0032(12) C26A 0.054(2) 0.050(2) 0.052(2) 0.0180(17) -0.0066(19) -0.0061(18) _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 C6 1.344(3) . ? N1 C2 1.349(3) . ? N1 C7 1.484(3) . ? N2 C25 1.367(3) . ? N2 S1 1.558(2) . ? S1 O1 1.430(2) . ? S1 O2 1.433(2) . ? S1 O3 1.630(2) . ? O3 C23 1.386(3) . ? O4 C25 1.232(3) . ? C2 C3 1.360(4) . ? C2 H2C 0.93(3) . ? C3 C4 1.374(4) . ? C3 H3A 0.97(3) . ? C4 C5 1.375(4) . ? C4 H4A 0.96(3) . ? C5 C6 1.366(4) . ? C5 H5A 0.92(3) . ? C6 H6A 0.93(3) . ? C7 C8 1.506(4) . ? C7 H7A 1.03(3) . ? C7 H7B 0.87(3) . ? C8 C9 1.538(4) . ? C8 H8A 0.90(3) . ? C8 H8B 0.99(3) . ? C9 C10 1.521(4) . ? C9 H9A 1.02(3) . ? C9 H9B 1.06(3) . ? C10 C11 1.527(4) . ? C10 H10A 1.00(3) . ? C10 H10B 0.96(3) . ? C11 C12 1.521(4) . ? C11 H11A 0.97(3) . ? C11 H11B 1.04(3) . ? C12 C13 1.525(4) . ? C12 H12A 0.98(3) . ? C12 H12B 1.07(3) . ? C13 C14 1.525(4) . ? C13 H13A 0.93(3) . ? C13 H13B 1.02(3) . ? C14 C15 1.517(4) . ? C14 H14A 1.05(3) . ? C14 H14B 0.99(3) . ? C15 C16 1.525(4) . ? C15 H15A 0.98(3) . ? C15 H15B 0.96(3) . ? C16 C17 1.521(4) . ? C16 H16A 0.96(3) . ? C16 H16B 1.03(3) . ? C17 C18 1.528(4) . ? C17 H17A 0.98(3) . ? C17 H17B 0.98(3) . ? C18 C19 1.521(4) . ? C18 H18A 1.03(3) . ? C18 H18B 1.00(3) . ? C19 C20 1.521(4) . ? C19 H19A 1.00(3) . ? C19 H19B 0.97(3) . ? C20 C21 1.513(4) . ? C20 H20A 1.04(3) . ? C20 H20B 0.95(3) . ? C21 C22 1.511(5) . ? C21 H21A 0.94(3) . ? C21 H21B 1.00(3) . ? C22 H22A 1.04(4) . ? C22 H22B 0.84(4) . ? C22 H22C 1.09(5) . ? C23 C24 1.315(4) . ? C23 C26 1.488(4) . ? C24 C25 1.471(4) . ? C24 H24A 0.87(3) . ? C26 H26A 0.80(4) . ? C26 H26B 1.01(4) . ? C26 H26C 1.02(5) . ? N1A C2A 1.349(3) . ? N1A C6A 1.350(4) . ? N1A C7A 1.484(3) . ? N2A C25A 1.361(3) . ? N2A S1A 1.563(2) . ? S1A O2A 1.426(2) . ? S1A O1A 1.427(2) . ? S1A O3A 1.6395(19) . ? O3A C23A 1.389(3) . ? O4A C25A 1.239(3) . ? C2A C3A 1.356(4) . ? C2A H2B 0.92(3) . ? C3A C4A 1.372(5) . ? C3A H3B 1.00(4) . ? C4A C5A 1.385(5) . ? C4A H4B 0.96(3) . ? C5A C6A 1.365(4) . ? C5A H5B 0.94(4) . ? C6A H6B 1.03(3) . ? C7A C8A 1.498(4) . ? C7A H7D 1.00(3) . ? C7A H7C 0.95(3) . ? C8A C9A 1.522(4) . ? C8A H8D 0.97(3) . ? C8A H8C 0.94(3) . ? C9A C10A 1.521(4) . ? C9A H9D 1.04(3) . ? C9A H9C 0.86(3) . ? C10A C11A 1.518(4) . ? C10A H10D 0.93(3) . ? C10A H10C 0.96(3) . ? C11A C12A 1.521(4) . ? C11A H11D 0.87(3) . ? C11A H11C 1.01(3) . ? C12A C13A 1.523(4) . ? C12A H12D 0.90(3) . ? C12A H12C 1.00(3) . ? C13A C14A 1.519(4) . ? C13A H13D 1.00(3) . ? C13A H13C 0.89(3) . ? C14A C15A 1.520(4) . ? C14A H14D 0.97(3) . ? C14A H14C 0.96(3) . ? C15A C16A 1.522(4) . ? C15A H15D 1.02(3) . ? C15A H15C 0.95(3) . ? C16A C17A 1.516(4) . ? C16A H16D 0.98(3) . ? C16A H16C 1.00(3) . ? C17A C18A 1.529(4) . ? C17A H17D 0.95(3) . ? C17A H17C 0.99(3) . ? C18A C19A 1.509(4) . ? C18A H18D 1.00(3) . ? C18A H18C 0.99(3) . ? C19A C20A 1.528(4) . ? C19A H19D 0.93(3) . ? C19A H19C 1.02(3) . ? C20A C21A 1.502(4) . ? C20A H20C 0.94(3) . ? C20A H20D 0.95(3) . ? C21A C22A 1.523(4) . ? C21A H21C 0.98(4) . ? C21A H21D 1.01(4) . ? C22A H22D 0.94(4) . ? C22A H22E 1.05(4) . ? C22A H22F 0.91(4) . ? C23A C24A 1.315(4) . ? C23A C26A 1.487(4) . ? C24A C25A 1.464(4) . ? C24A H24B 0.95(3) . ? C26A H26F 1.18(4) . ? C26A H26E 0.90(4) . ? C26A H26D 0.90(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 C6 N1 C2 120.4(2) . . ? C6 N1 C7 120.1(2) . . ? C2 N1 C7 119.5(2) . . ? C25 N2 S1 118.59(17) . . ? O1 S1 O2 115.84(13) . . ? O1 S1 N2 110.67(12) . . ? O2 S1 N2 113.63(12) . . ? O1 S1 O3 104.48(12) . . ? O2 S1 O3 104.92(11) . . ? N2 S1 O3 106.21(11) . . ? C23 O3 S1 114.88(16) . . ? N1 C2 C3 120.4(3) . . ? N1 C2 H2C 113.9(17) . . ? C3 C2 H2C 125.6(17) . . ? C2 C3 C4 120.1(3) . . ? C2 C3 H3A 119.9(15) . . ? C4 C3 H3A 119.7(15) . . ? C3 C4 C5 118.7(3) . . ? C3 C4 H4A 124.4(17) . . ? C5 C4 H4A 116.9(17) . . ? C6 C5 C4 120.0(3) . . ? C6 C5 H5A 118.3(18) . . ? C4 C5 H5A 121.7(18) . . ? N1 C6 C5 120.4(3) . . ? N1 C6 H6A 112.3(18) . . ? C5 C6 H6A 127.4(18) . . ? N1 C7 C8 113.0(2) . . ? N1 C7 H7A 103.4(17) . . ? C8 C7 H7A 109.4(18) . . ? N1 C7 H7B 103(2) . . ? C8 C7 H7B 111(2) . . ? H7A C7 H7B 117(3) . . ? C7 C8 C9 109.8(2) . . ? C7 C8 H8A 109.9(17) . . ? C9 C8 H8A 112.1(17) . . ? C7 C8 H8B 111.9(16) . . ? C9 C8 H8B 112.4(15) . . ? H8A C8 H8B 100(2) . . ? C10 C9 C8 113.8(2) . . ? C10 C9 H9A 113.1(14) . . ? C8 C9 H9A 108.8(14) . . ? C10 C9 H9B 108.7(16) . . ? C8 C9 H9B 107.1(16) . . ? H9A C9 H9B 105(2) . . ? C9 C10 C11 113.0(2) . . ? C9 C10 H10A 108.1(17) . . ? C11 C10 H10A 110.2(17) . . ? C9 C10 H10B 106.4(17) . . ? C11 C10 H10B 111.6(17) . . ? H10A C10 H10B 107(2) . . ? C12 C11 C10 112.5(2) . . ? C12 C11 H11A 112.6(15) . . ? C10 C11 H11A 106.5(15) . . ? C12 C11 H11B 108.6(15) . . ? C10 C11 H11B 109.5(15) . . ? H11A C11 H11B 107(2) . . ? C11 C12 C13 114.3(2) . . ? C11 C12 H12A 111.8(17) . . ? C13 C12 H12A 107.8(16) . . ? C11 C12 H12B 106.6(16) . . ? C13 C12 H12B 109.5(15) . . ? H12A C12 H12B 107(2) . . ? C12 C13 C14 113.3(2) . . ? C12 C13 H13A 109.7(18) . . ? C14 C13 H13A 110.5(18) . . ? C12 C13 H13B 109.0(17) . . ? C14 C13 H13B 111.3(17) . . ? H13A C13 H13B 102(2) . . ? C15 C14 C13 114.1(2) . . ? C15 C14 H14A 110.2(15) . . ? C13 C14 H14A 109.1(16) . . ? C15 C14 H14B 111.5(15) . . ? C13 C14 H14B 109.2(15) . . ? H14A C14 H14B 102(2) . . ? C14 C15 C16 113.0(2) . . ? C14 C15 H15A 108.6(16) . . ? C16 C15 H15A 110.6(16) . . ? C14 C15 H15B 109.8(18) . . ? C16 C15 H15B 111.3(18) . . ? H15A C15 H15B 103(2) . . ? C17 C16 C15 113.5(2) . . ? C17 C16 H16A 110.6(18) . . ? C15 C16 H16A 106.5(18) . . ? C17 C16 H16B 111.9(16) . . ? C15 C16 H16B 108.9(16) . . ? H16A C16 H16B 105(2) . . ? C16 C17 C18 113.6(2) . . ? C16 C17 H17A 110.0(17) . . ? C18 C17 H17A 108.0(17) . . ? C16 C17 H17B 108.8(16) . . ? C18 C17 H17B 111.5(16) . . ? H17A C17 H17B 105(2) . . ? C19 C18 C17 113.3(2) . . ? C19 C18 H18A 109.6(16) . . ? C17 C18 H18A 112.1(16) . . ? C19 C18 H18B 110.0(18) . . ? C17 C18 H18B 111.0(18) . . ? H18A C18 H18B 100(2) . . ? C20 C19 C18 114.5(2) . . ? C20 C19 H19A 111.2(17) . . ? C18 C19 H19A 109.3(17) . . ? C20 C19 H19B 111.6(17) . . ? C18 C19 H19B 106.1(17) . . ? H19A C19 H19B 103(2) . . ? C21 C20 C19 113.4(3) . . ? C21 C20 H20A 108.2(18) . . ? C19 C20 H20A 109.1(18) . . ? C21 C20 H20B 110.2(18) . . ? C19 C20 H20B 112.8(19) . . ? H20A C20 H20B 103(2) . . ? C22 C21 C20 114.7(3) . . ? C22 C21 H21A 109.1(19) . . ? C20 C21 H21A 108.8(19) . . ? C22 C21 H21B 108.2(18) . . ? C20 C21 H21B 111.3(17) . . ? H21A C21 H21B 104(3) . . ? C21 C22 H22A 107(2) . . ? C21 C22 H22B 110(3) . . ? H22A C22 H22B 116(4) . . ? C21 C22 H22C 113(2) . . ? H22A C22 H22C 100(3) . . ? H22B C22 H22C 112(4) . . ? C24 C23 O3 121.3(2) . . ? C24 C23 C26 126.7(3) . . ? O3 C23 C26 112.0(3) . . ? C23 C24 C25 123.7(3) . . ? C23 C24 H24A 120.4(17) . . ? C25 C24 H24A 115.3(17) . . ? O4 C25 N2 120.7(2) . . ? O4 C25 C24 121.1(2) . . ? N2 C25 C24 118.1(2) . . ? C23 C26 H26A 109(3) . . ? C23 C26 H26B 107(2) . . ? H26A C26 H26B 104(3) . . ? C23 C26 H26C 108(3) . . ? H26A C26 H26C 125(4) . . ? H26B C26 H26C 102(3) . . ? C2A N1A C6A 120.1(2) . . ? C2A N1A C7A 119.2(2) . . ? C6A N1A C7A 120.7(2) . . ? C25A N2A S1A 117.91(19) . . ? O2A S1A O1A 116.25(12) . . ? O2A S1A N2A 113.21(12) . . ? O1A S1A N2A 110.66(12) . . ? O2A S1A O3A 105.32(11) . . ? O1A S1A O3A 103.71(11) . . ? N2A S1A O3A 106.60(11) . . ? C23A O3A S1A 115.01(17) . . ? N1A C2A C3A 121.2(3) . . ? N1A C2A H2B 111.2(19) . . ? C3A C2A H2B 127.6(19) . . ? C2A C3A C4A 119.7(3) . . ? C2A C3A H3B 122(2) . . ? C4A C3A H3B 119(2) . . ? C3A C4A C5A 118.7(3) . . ? C3A C4A H4B 124(2) . . ? C5A C4A H4B 117(2) . . ? C6A C5A C4A 120.1(3) . . ? C6A C5A H5B 119(2) . . ? C4A C5A H5B 121(2) . . ? N1A C6A C5A 120.0(3) . . ? N1A C6A H6B 112.7(17) . . ? C5A C6A H6B 127.3(18) . . ? N1A C7A C8A 112.3(2) . . ? N1A C7A H7D 109.0(18) . . ? C8A C7A H7D 111.4(18) . . ? N1A C7A H7C 109.6(19) . . ? C8A C7A H7C 111.5(18) . . ? H7D C7A H7C 102(3) . . ? C7A C8A C9A 111.4(2) . . ? C7A C8A H8D 106.7(14) . . ? C9A C8A H8D 112.3(14) . . ? C7A C8A H8C 109.4(17) . . ? C9A C8A H8C 106.8(18) . . ? H8D C8A H8C 110(2) . . ? C10A C9A C8A 114.7(3) . . ? C10A C9A H9D 107.6(15) . . ? C8A C9A H9D 111.0(15) . . ? C10A C9A H9C 104.7(18) . . ? C8A C9A H9C 112.6(18) . . ? H9D C9A H9C 106(2) . . ? C11A C10A C9A 113.4(2) . . ? C11A C10A H10D 107.6(16) . . ? C9A C10A H10D 110.0(16) . . ? C11A C10A H10C 106.9(17) . . ? C9A C10A H10C 112.2(17) . . ? H10D C10A H10C 106(2) . . ? C10A C11A C12A 113.8(3) . . ? C10A C11A H11D 111.3(19) . . ? C12A C11A H11D 106.7(19) . . ? C10A C11A H11C 109.2(16) . . ? C12A C11A H11C 109.8(17) . . ? H11D C11A H11C 106(3) . . ? C11A C12A C13A 114.5(3) . . ? C11A C12A H12D 108(2) . . ? C13A C12A H12D 109(2) . . ? C11A C12A H12C 109.0(15) . . ? C13A C12A H12C 110.3(15) . . ? H12D C12A H12C 106(3) . . ? C14A C13A C12A 114.0(3) . . ? C14A C13A H13D 109.0(16) . . ? C12A C13A H13D 109.2(16) . . ? C14A C13A H13C 110(2) . . ? C12A C13A H13C 106(2) . . ? H13D C13A H13C 108(3) . . ? C13A C14A C15A 113.9(3) . . ? C13A C14A H14D 107.5(16) . . ? C15A C14A H14D 110.9(16) . . ? C13A C14A H14C 106(2) . . ? C15A C14A H14C 110(2) . . ? H14D C14A H14C 108(3) . . ? C14A C15A C16A 114.0(3) . . ? C14A C15A H15D 107.9(15) . . ? C16A C15A H15D 108.5(15) . . ? C14A C15A H15C 110.7(19) . . ? C16A C15A H15C 110.3(19) . . ? H15D C15A H15C 105(2) . . ? C17A C16A C15A 114.4(3) . . ? C17A C16A H16D 108.5(16) . . ? C15A C16A H16D 107.7(16) . . ? C17A C16A H16C 108.7(17) . . ? C15A C16A H16C 108.6(18) . . ? H16D C16A H16C 109(2) . . ? C16A C17A C18A 114.2(3) . . ? C16A C17A H17D 114.3(18) . . ? C18A C17A H17D 106.2(18) . . ? C16A C17A H17C 108.3(16) . . ? C18A C17A H17C 110.0(16) . . ? H17D C17A H17C 103(2) . . ? C19A C18A C17A 114.2(3) . . ? C19A C18A H18D 107.3(16) . . ? C17A C18A H18D 108.8(16) . . ? C19A C18A H18C 108.1(18) . . ? C17A C18A H18C 111.0(18) . . ? H18D C18A H18C 107(2) . . ? C18A C19A C20A 114.9(3) . . ? C18A C19A H19D 109.9(18) . . ? C20A C19A H19D 108.3(19) . . ? C18A C19A H19C 105.0(17) . . ? C20A C19A H19C 111.9(18) . . ? H19D C19A H19C 107(3) . . ? C21A C20A C19A 113.6(3) . . ? C21A C20A H20C 110(2) . . ? C19A C20A H20C 107(2) . . ? C21A C20A H20D 108(2) . . ? C19A C20A H20D 108(2) . . ? H20C C20A H20D 110(3) . . ? C20A C21A C22A 114.9(3) . . ? C20A C21A H21C 111(2) . . ? C22A C21A H21C 109(2) . . ? C20A C21A H21D 105(2) . . ? C22A C21A H21D 113(2) . . ? H21C C21A H21D 103(3) . . ? C21A C22A H22D 111(2) . . ? C21A C22A H22E 111(2) . . ? H22D C22A H22E 98(3) . . ? C21A C22A H22F 111(3) . . ? H22D C22A H22F 115(3) . . ? H22E C22A H22F 111(4) . . ? C24A C23A O3A 121.6(2) . . ? C24A C23A C26A 126.6(3) . . ? O3A C23A C26A 111.7(3) . . ? C23A C24A C25A 123.7(3) . . ? C23A C24A H24B 119.2(17) . . ? C25A C24A H24B 117.0(17) . . ? O4A C25A N2A 120.1(2) . . ? O4A C25A C24A 120.6(2) . . ? N2A C25A C24A 119.2(2) . . ? C23A C26A H26F 105(2) . . ? C23A C26A H26E 114(2) . . ? H26F C26A H26E 107(3) . . ? C23A C26A H26D 111(2) . . ? H26F C26A H26D 110(3) . . ? H26E C26A H26D 109(3) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 23.32 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.259 _refine_diff_density_min -0.429 _refine_diff_density_rms 0.057