# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_datosm _database_code_depnum_ccdc_archive 'CCDC 907949' #TrackingRef '14972_web_deposit_cif_file_0_MariaGarcia-Valverde_1351241367.datosm 3c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H17 N3 O3 S' _chemical_formula_sum 'C13 H17 N3 O3 S' _chemical_formula_weight 295.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.939(3) _cell_length_b 5.4586(9) _cell_length_c 16.280(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.807(3) _cell_angle_gamma 90.00 _cell_volume 1406.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2641 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 23.70 _exptl_crystal_description prism _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.90 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.241 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.614130 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details SADABS(SHELDRICK,2001) _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 13033 _diffrn_reflns_av_R_equivalents 0.0756 _diffrn_reflns_av_sigmaI/netI 0.0558 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.29 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2489 _reflns_number_gt 1910 _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^)+(0.0494P)^2^+0.6121P] 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 2489 _refine_ls_number_parameters 184 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0663 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.1280 _refine_ls_wR_factor_gt 0.1129 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 0.22789(4) 1.34663(13) 0.42421(5) 0.0483(3) Uani 1 1 d . . . O1 O 0.46199(12) 0.5958(4) 0.59447(11) 0.0553(5) Uani 1 1 d . . . O2 O 0.27357(13) 1.3260(4) 0.35409(13) 0.0693(7) Uani 1 1 d . . . O3 O 0.21364(14) 1.5873(4) 0.45490(15) 0.0717(7) Uani 1 1 d . . . N1 N 0.36311(12) 0.9050(4) 0.56535(12) 0.0354(5) Uani 1 1 d . . . N2 N 0.27036(13) 1.1911(4) 0.50339(13) 0.0399(5) Uani 1 1 d . . . N3 N 0.42901(15) 0.7589(4) 0.46437(13) 0.0511(6) Uani 1 1 d . . . H3 H 0.4632 0.6754 0.4383 0.061 Uiso 1 1 calc R . . C1 C 0.32859(15) 1.0303(4) 0.49784(14) 0.0342(6) Uani 1 1 d . . . C2 C 0.12125(17) 1.0009(5) 0.34925(16) 0.0470(7) Uani 1 1 d . . . H2 H 0.1682 0.9397 0.3272 0.056 Uiso 1 1 calc R . . C3 C 0.12907(16) 1.2041(5) 0.39962(15) 0.0385(6) Uani 1 1 d . . . C4 C 0.37178(17) 0.9407(5) 0.42576(15) 0.0440(7) Uani 1 1 d . . . H4A H 0.3316 0.8690 0.3831 0.053 Uiso 1 1 calc R . . H4B H 0.4020 1.0721 0.4020 0.053 Uiso 1 1 calc R . . C5 C -0.02630(17) 0.9728(5) 0.36306(16) 0.0457(7) Uani 1 1 d . . . C6 C 0.33839(16) 0.9377(5) 0.64950(15) 0.0417(6) Uani 1 1 d . . . H6 H 0.2960 1.0685 0.6463 0.050 Uiso 1 1 calc R . . C7 C 0.05885(18) 1.2936(6) 0.43091(19) 0.0558(8) Uani 1 1 d . . . H7 H 0.0631 1.4322 0.4643 0.067 Uiso 1 1 calc R . . C8 C 0.42308(16) 0.7344(5) 0.54489(16) 0.0409(6) Uani 1 1 d . . . C9 C 0.04413(18) 0.8882(5) 0.33147(17) 0.0500(7) Uani 1 1 d . . . H9 H 0.0397 0.7513 0.2972 0.060 Uiso 1 1 calc R . . C10 C -0.01761(18) 1.1781(6) 0.41277(19) 0.0597(8) Uani 1 1 d . . . H10 H -0.0647 1.2397 0.4345 0.072 Uiso 1 1 calc R . . C11 C -0.11033(18) 0.8468(7) 0.3439(2) 0.0688(9) Uani 1 1 d . . . H11A H -0.1432 0.8702 0.3890 0.103 Uiso 1 1 calc R . . H11B H -0.1015 0.6747 0.3361 0.103 Uiso 1 1 calc R . . H11C H -0.1399 0.9149 0.2943 0.103 Uiso 1 1 calc R . . C12 C 0.2969(2) 0.7086(6) 0.6778(2) 0.0715(10) Uani 1 1 d . . . H12A H 0.2525 0.6583 0.6362 0.107 Uiso 1 1 calc R . . H12B H 0.2737 0.7417 0.7285 0.107 Uiso 1 1 calc R . . H12C H 0.3382 0.5803 0.6868 0.107 Uiso 1 1 calc R . . C13 C 0.41329(19) 1.0234(7) 0.70842(17) 0.0644(9) Uani 1 1 d . . . H13A H 0.4547 0.8951 0.7159 0.097 Uiso 1 1 calc R . . H13B H 0.3949 1.0641 0.7608 0.097 Uiso 1 1 calc R . . H13C H 0.4378 1.1654 0.6859 0.097 Uiso 1 1 calc R . . 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 0.0418(4) 0.0433(4) 0.0575(5) 0.0161(3) -0.0044(3) -0.0019(3) O1 0.0562(12) 0.0631(13) 0.0468(11) 0.0050(10) 0.0068(9) 0.0291(10) O2 0.0482(12) 0.0962(17) 0.0636(13) 0.0386(12) 0.0073(10) -0.0041(11) O3 0.0674(14) 0.0328(11) 0.1062(18) 0.0089(11) -0.0256(13) 0.0002(10) N1 0.0317(11) 0.0406(12) 0.0337(11) -0.0001(9) 0.0032(9) 0.0079(9) N2 0.0364(12) 0.0396(12) 0.0429(12) 0.0039(10) 0.0007(10) 0.0048(10) N3 0.0504(14) 0.0633(16) 0.0413(13) -0.0001(11) 0.0124(10) 0.0208(12) C1 0.0291(13) 0.0363(14) 0.0364(13) 0.0009(11) 0.0007(11) -0.0051(11) C2 0.0394(15) 0.0543(17) 0.0475(16) -0.0018(13) 0.0065(13) 0.0111(13) C3 0.0380(14) 0.0386(15) 0.0377(13) 0.0069(11) -0.0007(11) 0.0048(11) C4 0.0420(15) 0.0506(16) 0.0396(14) 0.0031(12) 0.0062(12) 0.0040(13) C5 0.0408(15) 0.0550(18) 0.0400(14) 0.0019(13) -0.0010(12) 0.0011(13) C6 0.0388(14) 0.0509(16) 0.0361(14) 0.0011(12) 0.0079(12) 0.0123(12) C7 0.0499(18) 0.0534(18) 0.0640(19) -0.0215(15) 0.0068(15) 0.0026(14) C8 0.0351(14) 0.0451(16) 0.0427(15) -0.0020(12) 0.0049(12) 0.0064(12) C9 0.0496(17) 0.0519(17) 0.0472(16) -0.0120(13) -0.0002(13) 0.0019(14) C10 0.0400(16) 0.074(2) 0.066(2) -0.0161(17) 0.0123(14) 0.0049(16) C11 0.0465(18) 0.088(3) 0.070(2) -0.0097(19) -0.0010(16) -0.0096(17) C12 0.082(2) 0.070(2) 0.069(2) 0.0103(18) 0.0321(19) -0.0003(19) C13 0.0573(19) 0.087(2) 0.0458(17) -0.0176(16) -0.0062(15) 0.0161(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O2 1.429(2) . ? S1 O3 1.433(2) . ? S1 N2 1.623(2) . ? S1 C3 1.760(3) . ? O1 C8 1.221(3) . ? N1 C1 1.354(3) . ? N1 C8 1.403(3) . ? N1 C6 1.481(3) . ? N2 C1 1.289(3) . ? N3 C8 1.332(3) . ? N3 C4 1.441(3) . ? N3 H3 0.8600 . ? C1 C4 1.510(3) . ? C2 C9 1.374(4) . ? C2 C3 1.376(4) . ? C2 H2 0.9300 . ? C3 C7 1.373(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C9 1.369(4) . ? C5 C10 1.379(4) . ? C5 C11 1.505(4) . ? C6 C12 1.512(4) . ? C6 C13 1.514(4) . ? C6 H6 0.9800 . ? C7 C10 1.373(4) . ? C7 H7 0.9300 . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? 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 117.87(15) . . ? O2 S1 N2 112.90(12) . . ? O3 S1 N2 105.72(13) . . ? O2 S1 C3 108.08(13) . . ? O3 S1 C3 108.06(13) . . ? N2 S1 C3 103.13(11) . . ? C1 N1 C8 111.4(2) . . ? C1 N1 C6 124.3(2) . . ? C8 N1 C6 124.3(2) . . ? C1 N2 S1 122.47(18) . . ? C8 N3 C4 112.5(2) . . ? C8 N3 H3 123.7 . . ? C4 N3 H3 123.7 . . ? N2 C1 N1 120.9(2) . . ? N2 C1 C4 132.3(2) . . ? N1 C1 C4 106.8(2) . . ? C9 C2 C3 120.1(3) . . ? C9 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C7 C3 C2 119.2(3) . . ? C7 C3 S1 120.3(2) . . ? C2 C3 S1 120.5(2) . . ? N3 C4 C1 102.0(2) . . ? N3 C4 H4A 111.4 . . ? C1 C4 H4A 111.4 . . ? N3 C4 H4B 111.4 . . ? C1 C4 H4B 111.4 . . ? H4A C4 H4B 109.2 . . ? C9 C5 C10 117.7(3) . . ? C9 C5 C11 121.1(3) . . ? C10 C5 C11 121.2(3) . . ? N1 C6 C12 110.9(2) . . ? N1 C6 C13 110.3(2) . . ? C12 C6 C13 113.8(3) . . ? N1 C6 H6 107.2 . . ? C12 C6 H6 107.2 . . ? C13 C6 H6 107.2 . . ? C10 C7 C3 119.9(3) . . ? C10 C7 H7 120.0 . . ? C3 C7 H7 120.0 . . ? O1 C8 N3 128.5(2) . . ? O1 C8 N1 124.2(2) . . ? N3 C8 N1 107.3(2) . . ? C5 C9 C2 121.5(3) . . ? C5 C9 H9 119.3 . . ? C2 C9 H9 119.3 . . ? C7 C10 C5 121.6(3) . . ? C7 C10 H10 119.2 . . ? C5 C10 H10 119.2 . . ? C5 C11 H11A 109.5 . . ? C5 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C5 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C6 C12 H12A 109.5 . . ? C6 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C6 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C6 C13 H13A 109.5 . . ? C6 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C6 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 S1 N2 C1 -12.8(3) . . . . ? O3 S1 N2 C1 -143.0(2) . . . . ? C3 S1 N2 C1 103.6(2) . . . . ? S1 N2 C1 N1 179.51(18) . . . . ? S1 N2 C1 C4 -0.3(4) . . . . ? C8 N1 C1 N2 178.1(2) . . . . ? C6 N1 C1 N2 0.2(4) . . . . ? C8 N1 C1 C4 -2.1(3) . . . . ? C6 N1 C1 C4 -180.0(2) . . . . ? C9 C2 C3 C7 -0.7(4) . . . . ? C9 C2 C3 S1 178.9(2) . . . . ? O2 S1 C3 C7 -146.3(2) . . . . ? O3 S1 C3 C7 -17.7(3) . . . . ? N2 S1 C3 C7 94.0(2) . . . . ? O2 S1 C3 C2 34.1(2) . . . . ? O3 S1 C3 C2 162.7(2) . . . . ? N2 S1 C3 C2 -85.6(2) . . . . ? C8 N3 C4 C1 0.6(3) . . . . ? N2 C1 C4 N3 -179.3(3) . . . . ? N1 C1 C4 N3 0.9(3) . . . . ? C1 N1 C6 C12 114.0(3) . . . . ? C8 N1 C6 C12 -63.7(3) . . . . ? C1 N1 C6 C13 -119.1(3) . . . . ? C8 N1 C6 C13 63.3(3) . . . . ? C2 C3 C7 C10 1.0(4) . . . . ? S1 C3 C7 C10 -178.6(2) . . . . ? C4 N3 C8 O1 179.3(3) . . . . ? C4 N3 C8 N1 -1.8(3) . . . . ? C1 N1 C8 O1 -178.6(3) . . . . ? C6 N1 C8 O1 -0.7(4) . . . . ? C1 N1 C8 N3 2.5(3) . . . . ? C6 N1 C8 N3 -179.6(2) . . . . ? C10 C5 C9 C2 0.8(4) . . . . ? C11 C5 C9 C2 -179.4(3) . . . . ? C3 C2 C9 C5 -0.2(4) . . . . ? C3 C7 C10 C5 -0.3(5) . . . . ? C9 C5 C10 C7 -0.6(5) . . . . ? C11 C5 C10 C7 179.7(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.288 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.046 data_datosm3 _database_code_depnum_ccdc_archive 'CCDC 907950' #TrackingRef '14973_web_deposit_cif_file_1_MariaGarcia-Valverde_1351241367.DATOSm 4f.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H27 N3 O3 S' _chemical_formula_sum 'C23 H27 N3 O3 S' _chemical_formula_weight 425.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 13.1137(14) _cell_length_b 6.2475(7) _cell_length_c 14.2342(16) _cell_angle_alpha 90.00 _cell_angle_beta 113.906(2) _cell_angle_gamma 90.00 _cell_volume 1066.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4073 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 25.14 _exptl_crystal_description prism _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.9 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 452 _exptl_absorpt_coefficient_mu 0.182 _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 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10556 _diffrn_reflns_av_R_equivalents 0.1630 _diffrn_reflns_av_sigmaI/netI 0.1186 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3769 _reflns_number_gt 3267 _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^)+(0.0840P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983),2074 Friedel pairs, Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.42(11) _refine_ls_number_reflns 3769 _refine_ls_number_parameters 273 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0774 _refine_ls_R_factor_gt 0.0722 _refine_ls_wR_factor_ref 0.1536 _refine_ls_wR_factor_gt 0.1506 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.007 _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 0.62358(7) 0.38284(13) 0.48184(5) 0.0332(2) Uani 1 1 d . . . O1 O 0.2412(3) 0.1743(5) 0.0852(2) 0.0584(8) Uani 1 1 d . . . O2 O 0.5523(2) 0.5144(4) 0.51193(19) 0.0439(6) Uani 1 1 d . . . O3 O 0.6913(2) 0.2287(4) 0.55463(18) 0.0438(6) Uani 1 1 d . . . N1 N 0.3762(2) 0.4165(5) 0.3236(2) 0.0384(7) Uani 1 1 d . . . H1 H 0.3867 0.4993 0.3750 0.046 Uiso 1 1 calc R . . N2 N 0.4120(3) 0.1956(5) 0.2206(2) 0.0358(7) Uani 1 1 d . . . N3 N 0.5592(3) 0.2593(4) 0.3748(2) 0.0336(7) Uani 1 1 d . . . C1 C 0.1842(4) 0.2712(7) 0.2675(3) 0.0550(11) Uani 1 1 d . . . H1A H 0.1408 0.1784 0.2106 0.066 Uiso 1 1 calc R . . H1B H 0.2269 0.1790 0.3248 0.066 Uiso 1 1 calc R . . C2 C 0.1051(4) 0.3908(11) 0.2966(4) 0.0696(13) Uani 1 1 d . . . H2A H 0.1438 0.5103 0.3399 0.084 Uiso 1 1 calc R . . H2B H 0.0787 0.2982 0.3367 0.084 Uiso 1 1 calc R . . C3 C 0.0033(4) 0.4771(9) 0.2032(4) 0.0722(14) Uani 1 1 d . . . H3A H -0.0282 0.3593 0.1559 0.087 Uiso 1 1 calc R . . H3B H -0.0526 0.5221 0.2274 0.087 Uiso 1 1 calc R . . C4 C 0.0232(4) 0.6600(10) 0.1437(4) 0.0803(16) Uani 1 1 d . . . H4A H 0.0435 0.7850 0.1879 0.096 Uiso 1 1 calc R . . H4B H -0.0466 0.6920 0.0862 0.096 Uiso 1 1 calc R . . C5 C 0.1119(4) 0.6260(9) 0.1025(3) 0.0645(13) Uani 1 1 d . . . H5A H 0.0950 0.4955 0.0621 0.077 Uiso 1 1 calc R . . H5B H 0.1087 0.7436 0.0569 0.077 Uiso 1 1 calc R . . C6 C 0.2294(4) 0.6104(6) 0.1848(3) 0.0464(9) Uani 1 1 d . . . H6A H 0.2365 0.7132 0.2381 0.056 Uiso 1 1 calc R . . H6B H 0.2804 0.6543 0.1545 0.056 Uiso 1 1 calc R . . C7 C 0.2683(3) 0.3921(7) 0.2362(2) 0.0377(7) Uani 1 1 d . . . C8 C 0.3010(3) 0.2443(6) 0.1685(2) 0.0386(8) Uani 1 1 d . . . C9 C 0.4562(3) 0.2972(5) 0.3153(2) 0.0316(7) Uani 1 1 d . . . C10 C 0.7124(3) 0.5517(6) 0.4501(3) 0.0343(8) Uani 1 1 d . . . C11 C 0.6806(3) 0.7576(6) 0.4190(3) 0.0416(9) Uani 1 1 d . . . H11 H 0.6169 0.8146 0.4230 0.050 Uiso 1 1 calc R . . C12 C 0.7432(3) 0.8791(7) 0.3819(3) 0.0451(8) Uani 1 1 d . . . H12 H 0.7202 1.0177 0.3595 0.054 Uiso 1 1 calc R . . C13 C 0.8401(4) 0.8009(6) 0.3770(3) 0.0446(9) Uani 1 1 d . . . C14 C 0.8727(4) 0.5970(6) 0.4128(3) 0.0501(10) Uani 1 1 d . . . H14 H 0.9387 0.5429 0.4126 0.060 Uiso 1 1 calc R . . C15 C 0.8100(3) 0.4697(6) 0.4492(3) 0.0447(9) Uani 1 1 d . . . H15 H 0.8332 0.3317 0.4725 0.054 Uiso 1 1 calc R . . C16 C 0.9036(5) 0.9375(7) 0.3331(4) 0.0663(13) Uani 1 1 d . . . H16A H 0.8608 0.9554 0.2607 0.099 Uiso 1 1 calc R . . H16B H 0.9734 0.8699 0.3444 0.099 Uiso 1 1 calc R . . H16C H 0.9175 1.0750 0.3661 0.099 Uiso 1 1 calc R . . C17 C 0.4714(3) 0.0398(6) 0.1854(3) 0.0400(8) Uani 1 1 d . . . H17A H 0.4168 -0.0455 0.1314 0.048 Uiso 1 1 calc R . . H17B H 0.5117 -0.0558 0.2420 0.048 Uiso 1 1 calc R . . C18 C 0.5529(3) 0.1296(6) 0.1451(3) 0.0381(8) Uani 1 1 d . . . C19 C 0.5960(4) 0.3332(7) 0.1651(3) 0.0479(10) Uani 1 1 d . . . H19 H 0.5721 0.4272 0.2026 0.057 Uiso 1 1 calc R . . C20 C 0.6752(4) 0.3992(9) 0.1296(3) 0.0611(11) Uani 1 1 d . . . H20 H 0.7048 0.5365 0.1443 0.073 Uiso 1 1 calc R . . C21 C 0.7098(4) 0.2629(11) 0.0732(3) 0.0676(14) Uani 1 1 d . . . H21 H 0.7619 0.3078 0.0484 0.081 Uiso 1 1 calc R . . C22 C 0.6676(5) 0.0630(11) 0.0538(4) 0.0696(14) Uani 1 1 d . . . H22 H 0.6918 -0.0308 0.0163 0.084 Uiso 1 1 calc R . . C23 C 0.5884(4) -0.0046(8) 0.0891(3) 0.0554(11) Uani 1 1 d . . . H23 H 0.5595 -0.1424 0.0744 0.066 Uiso 1 1 calc R . . 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 0.0260(4) 0.0484(5) 0.0253(4) 0.0003(4) 0.0104(3) 0.0003(4) O1 0.0390(18) 0.0842(19) 0.0416(15) -0.0162(14) 0.0058(13) -0.0027(15) O2 0.0361(16) 0.0639(16) 0.0351(13) -0.0133(12) 0.0178(12) -0.0008(13) O3 0.0353(15) 0.0600(15) 0.0335(12) 0.0105(11) 0.0113(11) 0.0014(12) N1 0.0277(17) 0.0564(19) 0.0292(13) -0.0073(13) 0.0098(12) 0.0057(14) N2 0.0316(18) 0.0478(16) 0.0311(14) -0.0063(12) 0.0158(13) -0.0015(13) N3 0.0259(17) 0.0455(16) 0.0312(14) -0.0026(13) 0.0135(13) -0.0001(13) C1 0.042(3) 0.072(3) 0.057(2) 0.016(2) 0.026(2) 0.001(2) C2 0.051(3) 0.101(3) 0.063(2) -0.004(3) 0.030(2) -0.016(3) C3 0.033(3) 0.103(4) 0.080(3) -0.017(3) 0.023(3) 0.000(3) C4 0.037(3) 0.111(4) 0.085(4) 0.015(3) 0.017(3) 0.030(3) C5 0.055(3) 0.088(3) 0.042(2) 0.013(2) 0.011(2) 0.019(3) C6 0.037(2) 0.063(2) 0.041(2) 0.0038(17) 0.0180(18) 0.0015(19) C7 0.0261(18) 0.0571(19) 0.0298(15) 0.0006(18) 0.0112(14) -0.0002(19) C8 0.035(2) 0.050(2) 0.0306(18) -0.0009(15) 0.0131(17) -0.0053(17) C9 0.031(2) 0.0397(16) 0.0274(15) -0.0004(13) 0.0154(15) -0.0029(15) C10 0.030(2) 0.0424(18) 0.0302(17) -0.0006(14) 0.0114(15) 0.0003(15) C11 0.035(2) 0.048(2) 0.0433(19) -0.0009(16) 0.0173(17) 0.0037(17) C12 0.043(2) 0.0443(18) 0.0473(18) 0.0020(19) 0.0173(17) -0.003(2) C13 0.040(2) 0.054(2) 0.0421(19) -0.0037(16) 0.0184(18) -0.0084(18) C14 0.038(3) 0.060(3) 0.060(3) 0.002(2) 0.028(2) 0.000(2) C15 0.033(2) 0.048(2) 0.053(2) 0.0006(17) 0.0169(18) 0.0014(16) C16 0.059(3) 0.077(3) 0.070(3) 0.005(2) 0.033(3) -0.012(2) C17 0.041(2) 0.0431(18) 0.0377(18) -0.0077(15) 0.0174(17) -0.0034(16) C18 0.029(2) 0.057(2) 0.0266(16) -0.0022(15) 0.0098(15) 0.0037(17) C19 0.046(2) 0.060(3) 0.0443(19) 0.0019(17) 0.0246(18) 0.0028(19) C20 0.049(3) 0.080(3) 0.056(2) 0.012(3) 0.022(2) -0.008(3) C21 0.038(3) 0.128(4) 0.041(2) 0.011(3) 0.021(2) 0.005(3) C22 0.056(3) 0.110(4) 0.054(3) -0.011(3) 0.034(3) 0.010(3) C23 0.054(3) 0.073(3) 0.042(2) -0.0117(19) 0.023(2) 0.003(2) _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 O3 1.430(3) . ? S1 O2 1.434(3) . ? S1 N3 1.608(3) . ? S1 C10 1.760(4) . ? O1 C8 1.208(5) . ? N1 C9 1.332(4) . ? N1 C7 1.465(4) . ? N1 H1 0.8600 . ? N2 C8 1.373(5) . ? N2 C9 1.387(4) . ? N2 C17 1.456(4) . ? N3 C9 1.292(4) . ? C1 C2 1.468(6) . ? C1 C7 1.544(5) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.550(7) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.506(8) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.515(7) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.514(6) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.534(6) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.516(5) . ? C10 C11 1.369(5) . ? C10 C15 1.384(5) . ? C11 C12 1.371(5) . ? C11 H11 0.9300 . ? C12 C13 1.389(5) . ? C12 H12 0.9300 . ? C13 C14 1.374(6) . ? C13 C16 1.495(6) . ? C14 C15 1.386(5) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.511(5) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C23 1.363(5) . ? C18 C19 1.374(6) . ? C19 C20 1.388(6) . ? C19 H19 0.9300 . ? C20 C21 1.369(7) . ? C20 H20 0.9300 . ? C21 C22 1.349(8) . ? C21 H21 0.9300 . ? C22 C23 1.390(7) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? 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 O3 S1 O2 117.28(15) . . ? O3 S1 N3 107.25(15) . . ? O2 S1 N3 113.74(16) . . ? O3 S1 C10 107.95(17) . . ? O2 S1 C10 108.18(16) . . ? N3 S1 C10 101.09(15) . . ? C9 N1 C7 113.0(3) . . ? C9 N1 H1 123.5 . . ? C7 N1 H1 123.5 . . ? C8 N2 C9 111.0(3) . . ? C8 N2 C17 124.1(3) . . ? C9 N2 C17 124.7(3) . . ? C9 N3 S1 122.7(2) . . ? C2 C1 C7 120.1(4) . . ? C2 C1 H1A 107.3 . . ? C7 C1 H1A 107.3 . . ? C2 C1 H1B 107.3 . . ? C7 C1 H1B 107.3 . . ? H1A C1 H1B 106.9 . . ? C1 C2 C3 113.3(4) . . ? C1 C2 H2A 108.9 . . ? C3 C2 H2A 108.9 . . ? C1 C2 H2B 108.9 . . ? C3 C2 H2B 108.9 . . ? H2A C2 H2B 107.7 . . ? C4 C3 C2 117.4(4) . . ? C4 C3 H3A 107.9 . . ? C2 C3 H3A 107.9 . . ? C4 C3 H3B 107.9 . . ? C2 C3 H3B 107.9 . . ? H3A C3 H3B 107.2 . . ? C3 C4 C5 116.5(4) . . ? C3 C4 H4A 108.2 . . ? C5 C4 H4A 108.2 . . ? C3 C4 H4B 108.2 . . ? C5 C4 H4B 108.2 . . ? H4A C4 H4B 107.3 . . ? C6 C5 C4 114.2(4) . . ? C6 C5 H5A 108.7 . . ? C4 C5 H5A 108.7 . . ? C6 C5 H5B 108.7 . . ? C4 C5 H5B 108.7 . . ? H5A C5 H5B 107.6 . . ? C5 C6 C7 117.6(4) . . ? C5 C6 H6A 107.9 . . ? C7 C6 H6A 107.9 . . ? C5 C6 H6B 107.9 . . ? C7 C6 H6B 107.9 . . ? H6A C6 H6B 107.2 . . ? N1 C7 C8 100.4(3) . . ? N1 C7 C6 109.4(3) . . ? C8 C7 C6 111.3(3) . . ? N1 C7 C1 111.2(3) . . ? C8 C7 C1 107.7(3) . . ? C6 C7 C1 115.7(3) . . ? O1 C8 N2 125.1(3) . . ? O1 C8 C7 127.3(4) . . ? N2 C8 C7 107.6(3) . . ? N3 C9 N1 134.1(3) . . ? N3 C9 N2 117.9(3) . . ? N1 C9 N2 107.9(3) . . ? C11 C10 C15 120.4(4) . . ? C11 C10 S1 120.0(3) . . ? C15 C10 S1 119.5(3) . . ? C10 C11 C12 119.6(4) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C11 C12 C13 121.8(4) . . ? C11 C12 H12 119.1 . . ? C13 C12 H12 119.1 . . ? C14 C13 C12 117.5(4) . . ? C14 C13 C16 122.8(4) . . ? C12 C13 C16 119.7(4) . . ? C13 C14 C15 121.9(4) . . ? C13 C14 H14 119.1 . . ? C15 C14 H14 119.1 . . ? C10 C15 C14 118.8(4) . . ? C10 C15 H15 120.6 . . ? C14 C15 H15 120.6 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N2 C17 C18 116.2(3) . . ? N2 C17 H17A 108.2 . . ? C18 C17 H17A 108.2 . . ? N2 C17 H17B 108.2 . . ? C18 C17 H17B 108.2 . . ? H17A C17 H17B 107.4 . . ? C23 C18 C19 118.8(4) . . ? C23 C18 C17 117.1(3) . . ? C19 C18 C17 124.1(3) . . ? C18 C19 C20 120.3(4) . . ? C18 C19 H19 119.8 . . ? C20 C19 H19 119.8 . . ? C21 C20 C19 120.3(5) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? C22 C21 C20 119.3(5) . . ? C22 C21 H21 120.3 . . ? C20 C21 H21 120.3 . . ? C21 C22 C23 120.8(5) . . ? C21 C22 H22 119.6 . . ? C23 C22 H22 119.6 . . ? C18 C23 C22 120.5(5) . . ? C18 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 S1 N3 C9 140.0(3) . . . . ? O2 S1 N3 C9 8.6(3) . . . . ? C10 S1 N3 C9 -107.1(3) . . . . ? C7 C1 C2 C3 79.2(5) . . . . ? C1 C2 C3 C4 -71.5(6) . . . . ? C2 C3 C4 C5 55.4(7) . . . . ? C3 C4 C5 C6 -67.5(7) . . . . ? C4 C5 C6 C7 83.5(6) . . . . ? C9 N1 C7 C8 -3.9(4) . . . . ? C9 N1 C7 C6 -121.0(3) . . . . ? C9 N1 C7 C1 109.9(3) . . . . ? C5 C6 C7 N1 -171.1(3) . . . . ? C5 C6 C7 C8 78.9(4) . . . . ? C5 C6 C7 C1 -44.5(5) . . . . ? C2 C1 C7 N1 95.3(4) . . . . ? C2 C1 C7 C8 -155.7(4) . . . . ? C2 C1 C7 C6 -30.4(5) . . . . ? C9 N2 C8 O1 -178.3(4) . . . . ? C17 N2 C8 O1 -4.5(6) . . . . ? C9 N2 C8 C7 -0.5(4) . . . . ? C17 N2 C8 C7 173.3(3) . . . . ? N1 C7 C8 O1 -179.7(4) . . . . ? C6 C7 C8 O1 -64.0(5) . . . . ? C1 C7 C8 O1 63.8(5) . . . . ? N1 C7 C8 N2 2.5(3) . . . . ? C6 C7 C8 N2 118.2(3) . . . . ? C1 C7 C8 N2 -114.0(3) . . . . ? S1 N3 C9 N1 -6.6(6) . . . . ? S1 N3 C9 N2 174.3(2) . . . . ? C7 N1 C9 N3 -175.3(4) . . . . ? C7 N1 C9 N2 3.8(4) . . . . ? C8 N2 C9 N3 177.3(3) . . . . ? C17 N2 C9 N3 3.6(5) . . . . ? C8 N2 C9 N1 -2.0(4) . . . . ? C17 N2 C9 N1 -175.8(3) . . . . ? O3 S1 C10 C11 -152.6(3) . . . . ? O2 S1 C10 C11 -24.8(3) . . . . ? N3 S1 C10 C11 95.0(3) . . . . ? O3 S1 C10 C15 32.5(3) . . . . ? O2 S1 C10 C15 160.3(3) . . . . ? N3 S1 C10 C15 -79.9(3) . . . . ? C15 C10 C11 C12 3.2(5) . . . . ? S1 C10 C11 C12 -171.7(3) . . . . ? C10 C11 C12 C13 -1.4(5) . . . . ? C11 C12 C13 C14 -1.3(6) . . . . ? C11 C12 C13 C16 178.2(4) . . . . ? C12 C13 C14 C15 2.3(6) . . . . ? C16 C13 C14 C15 -177.2(4) . . . . ? C11 C10 C15 C14 -2.2(6) . . . . ? S1 C10 C15 C14 172.7(3) . . . . ? C13 C14 C15 C10 -0.6(6) . . . . ? C8 N2 C17 C18 107.5(4) . . . . ? C9 N2 C17 C18 -79.6(4) . . . . ? N2 C17 C18 C23 -164.2(3) . . . . ? N2 C17 C18 C19 18.5(5) . . . . ? C23 C18 C19 C20 -0.7(6) . . . . ? C17 C18 C19 C20 176.5(4) . . . . ? C18 C19 C20 C21 0.9(6) . . . . ? C19 C20 C21 C22 -1.0(7) . . . . ? C20 C21 C22 C23 1.0(7) . . . . ? C19 C18 C23 C22 0.6(6) . . . . ? C17 C18 C23 C22 -176.8(4) . . . . ? C21 C22 C23 C18 -0.8(7) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.482 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.066