data_global #TrackingRef 'C0SC00335B_ccdc_780815_780821_cif.txt' _journal_name_full 'Chemical Science' _journal_coden_cambridge 1475 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Antonio M. Echavarren' _publ_contact_author_email aechavarren@iciq.es loop_ _publ_author_name 'Patricia Perez-Galan' 'Elena Herrero-Gomez' 'Daniel T. Hog' 'Nolwenn J. A. Martin' 'Feliu Maseras' ; A.M.Echavarren ; data_ehg145_0m #TrackingRef 'C0SC00335B_ccdc_780815_780821_cif.txt' _database_code_depnum_ccdc_archive 'CCDC 780815' #TrackingRef 'web_deposit_cif_file_0_AntonioM.Echavarren_1276529606.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25.50 H29.50 Cl1.50 N O2 S' _chemical_formula_weight 467.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 35.8601(11) _cell_length_b 6.0216(2) _cell_length_c 23.1924(6) _cell_angle_alpha 90.00 _cell_angle_beta 111.9790(10) _cell_angle_gamma 90.00 _cell_volume 4644.1(2) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3632 _cell_measurement_theta_min 3.44 _cell_measurement_theta_max 31.23 _exptl_crystal_description BLOCK _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.337 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1976 _exptl_absorpt_coefficient_mu 0.335 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9376 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details ; SADABS Version 2008/1 Bruker-Nonius Blessing, Acta Cryst. (1995) A51 33-38 ; _exptl_special_details ; It should be noted that the esd's of the cell dimensions are probably too low; they should be multiplied by a factor of 2 to 10 ; _diffrn_ambient_temperature 100(2) _diffrn_measurement_specimen_suppport 'magnetic support whith 10 micron nylon fiber cryoloop' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'rotating anode X-ray tube' _diffrn_source_type 'Bruker-Nonius FR 591' _diffrn_source_power 50 _diffrn_source_current 70 _diffrn_source_size '3 mm x 0.3 mm fine focus' _diffrn_radiation_monochromator 'Multilayer Montel 200 mirrors' _diffrn_detector_type '4K CCD area detector APEX II' _diffrn_measurement_device_type 'Kappa 4-axis goniometer bruker-nonius' _diffrn_measurement_method ; Fullsphere data collection, phi and omega scans ; _diffrn_detector_area_resol_mean 512 _diffrn_reflns_number 15608 _diffrn_reflns_av_R_equivalents 0.0315 _diffrn_reflns_av_sigmaI/netI 0.0460 _diffrn_reflns_limit_h_min -52 _diffrn_reflns_limit_h_max 42 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 3.44 _diffrn_reflns_theta_max 31.51 _reflns_number_total 7482 _reflns_number_gt 5749 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 v2009.1-0' _computing_cell_refinement 'Bruker APEX2 v2009.1-0' _computing_data_reduction 'Bruker SAINT V7.60A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXS-97 (Sheldrick, 2008)' _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. Ther is disorder in two carbon atoms with occupation ratio of 58:42. In the asymmetric unit there is half cloroform molecule on a special position. ; _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^)+(0.0934P)^2^+5.8201P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7482 _refine_ls_number_parameters 317 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0770 _refine_ls_R_factor_gt 0.0592 _refine_ls_wR_factor_ref 0.1786 _refine_ls_wR_factor_gt 0.1641 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 S1 S 0.155742(12) 0.58441(8) 1.166024(17) 0.01880(12) Uani 1 1 d . . . O1 O 0.15277(4) 0.7414(3) 1.21043(6) 0.0258(3) Uani 1 1 d . . . C1 C 0.20503(5) 0.6018(3) 1.16672(7) 0.0172(3) Uani 1 1 d . . . N1 N 0.12496(4) 0.6654(3) 1.09783(6) 0.0186(3) Uani 1 1 d . . . C1S C 0.23511(19) 0.8762(11) 0.0212(2) 0.0510(14) Uani 0.50 1 d P A -1 H1SA H 0.2370 0.8384 0.0642 0.061 Uiso 0.50 1 calc PR A -1 Cl1S Cl 0.27904(4) 1.0407(4) 0.02839(9) 0.0751(6) Uani 0.50 1 d P A -1 O2 O 0.14716(4) 0.3538(2) 1.17110(6) 0.0248(3) Uani 1 1 d . . . C2 C 0.22136(6) 0.4211(3) 1.14718(8) 0.0220(3) Uani 1 1 d . . . H2A H 0.2058 0.2912 1.1317 0.026 Uiso 1 1 calc R . . Cl2S Cl 0.19290(4) 1.0448(3) -0.01237(7) 0.0541(4) Uani 0.50 1 d P A -1 C3 C 0.26092(6) 0.4329(3) 1.15053(8) 0.0234(4) Uani 1 1 d . . . H3A H 0.2722 0.3093 1.1374 0.028 Uiso 1 1 calc R . . Cl3S Cl 0.23398(7) 0.6320(3) -0.01696(8) 0.0694(5) Uani 0.50 1 d P A -1 C4 C 0.28423(5) 0.6221(3) 1.17272(8) 0.0212(3) Uani 1 1 d . . . C5 C 0.26685(5) 0.8036(3) 1.19051(7) 0.0205(3) Uani 1 1 d . . . H5A H 0.2821 0.9354 1.2044 0.025 Uiso 1 1 calc R . . C6 C 0.22751(5) 0.7951(3) 1.18824(7) 0.0192(3) Uani 1 1 d . . . H6A H 0.2161 0.9189 1.2011 0.023 Uiso 1 1 calc R . . C7 C 0.32757(6) 0.6301(4) 1.17915(10) 0.0297(4) Uani 1 1 d . . . H7A H 0.3348 0.4898 1.1646 0.045 Uiso 1 1 calc R . . H7B H 0.3448 0.6530 1.2229 0.045 Uiso 1 1 calc R . . H7C H 0.3314 0.7529 1.1542 0.045 Uiso 1 1 calc R . . C8 C 0.12694(5) 0.8984(3) 1.07826(8) 0.0199(3) Uani 1 1 d . . . H81 H 0.1542 0.9363 1.0802 0.024 Uiso 1 1 calc R . . H82 H 0.1190 1.0041 1.1043 0.024 Uiso 1 1 calc R . . C9 C 0.09681(5) 0.8977(3) 1.01182(7) 0.0167(3) Uani 1 1 d . . . H10 H 0.0983 1.0155 0.9824 0.020 Uiso 1 1 calc R . . C10 C 0.05688(5) 0.7893(3) 1.00201(7) 0.0162(3) Uani 1 1 d . . . H13A H 0.0528 0.7486 1.0410 0.019 Uiso 1 1 calc R . . C11 C 0.08960(5) 0.6584(3) 0.99009(7) 0.0154(3) Uani 1 1 d . . . C12 C 0.11557(5) 0.5150(3) 1.04399(7) 0.0181(3) Uani 1 1 d . . . H12A H 0.1007 0.3824 1.0488 0.022 Uiso 1 1 calc R . . H12B H 0.1404 0.4668 1.0383 0.022 Uiso 1 1 calc R . . C13 C 0.01936(5) 0.8457(3) 0.94808(7) 0.0162(3) Uani 1 1 d . . . C14 C -0.01078(5) 0.6848(3) 0.92612(7) 0.0201(3) Uani 1 1 d . . . H14 H -0.0066 0.5420 0.9449 0.024 Uiso 1 1 calc R . . C15 C -0.04693(5) 0.7308(4) 0.87697(8) 0.0242(4) Uani 1 1 d . . . H15 H -0.0673 0.6203 0.8629 0.029 Uiso 1 1 calc R . . C16 C -0.05314(6) 0.9376(4) 0.84869(8) 0.0254(4) Uani 1 1 d . . . H16 H -0.0777 0.9692 0.8152 0.031 Uiso 1 1 calc R . . C17 C -0.02344(6) 1.0973(4) 0.86947(8) 0.0257(4) Uani 1 1 d . . . H17 H -0.0275 1.2384 0.8498 0.031 Uiso 1 1 calc R . . C18 C 0.01261(5) 1.0527(3) 0.91938(8) 0.0210(3) Uani 1 1 d . . . H18 H 0.0326 1.1648 0.9338 0.025 Uiso 1 1 calc R . . C19 C 0.08280(5) 0.5803(3) 0.92594(7) 0.0163(3) Uani 1 1 d . . . H19 H 0.0633 0.4546 0.9115 0.020 Uiso 1 1 calc R . . C20 C 0.11641(6) 0.5711(4) 0.90184(9) 0.0253(4) Uani 1 1 d . B . H20 H 0.1425 0.6365 0.9299 0.030 Uiso 1 1 calc R . . C21 C 0.11991(6) 0.3732(4) 0.86340(10) 0.0328(5) Uani 1 1 d . . . H213 H 0.1132 0.2357 0.8809 0.039 Uiso 0.572(7) 1 calc PR B 2 H214 H 0.1480 0.3606 0.8660 0.039 Uiso 0.572(7) 1 calc PR B 2 H211 H 0.1289 0.2469 0.8903 0.039 Uiso 0.428(7) 1 d PR B 1 H212 H 0.1398 0.4044 0.8461 0.039 Uiso 0.428(7) 1 d PR B 1 C22 C 0.08067(16) 0.3156(8) 0.8117(2) 0.0261(12) Uani 0.428(7) 1 d P B 1 H222 H 0.0603 0.2694 0.8287 0.031 Uiso 0.428(7) 1 calc PR B 1 H221 H 0.0844 0.1939 0.7857 0.031 Uiso 0.428(7) 1 calc PR B 1 C22' C 0.09073(13) 0.3960(9) 0.79229(19) 0.0348(11) Uani 0.572(7) 1 d P B 2 H224 H 0.1012 0.5122 0.7721 0.042 Uiso 0.572(7) 1 calc PR B 2 H223 H 0.0902 0.2538 0.7706 0.042 Uiso 0.572(7) 1 calc PR B 2 C23 C 0.06771(15) 0.5300(9) 0.77380(19) 0.0268(12) Uani 0.428(7) 1 d P B 1 H232 H 0.0465 0.4963 0.7329 0.032 Uiso 0.428(7) 1 calc PR B 1 H231 H 0.0909 0.5950 0.7666 0.032 Uiso 0.428(7) 1 calc PR B 1 C23' C 0.04833(12) 0.4561(8) 0.78629(16) 0.0339(11) Uani 0.572(7) 1 d P B 2 H233 H 0.0390 0.3567 0.8122 0.041 Uiso 0.572(7) 1 calc PR B 2 H234 H 0.0294 0.4444 0.7425 0.041 Uiso 0.572(7) 1 calc PR B 2 C24 C 0.05124(9) 0.7019(4) 0.80974(9) 0.0416(6) Uani 1 1 d . . . H253 H 0.0581 0.7990 0.7807 0.050 Uiso 0.572(7) 1 calc PR B 2 H254 H 0.0246 0.7485 0.8090 0.050 Uiso 0.572(7) 1 calc PR B 2 H251 H 0.0268 0.6461 0.8121 0.050 Uiso 0.428(7) 1 d PR B 1 H252 H 0.0455 0.8411 0.7880 0.050 Uiso 0.428(7) 1 d PR B 1 C25 C 0.08227(7) 0.7348(3) 0.87489(8) 0.0270(4) Uani 1 1 d . B . H25 H 0.0891 0.8929 0.8877 0.032 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 0.01746(19) 0.0233(2) 0.01259(17) -0.00013(14) 0.00214(13) -0.00215(15) O1 0.0241(6) 0.0357(8) 0.0164(5) -0.0061(5) 0.0062(5) -0.0013(6) C1 0.0172(7) 0.0185(8) 0.0127(6) 0.0011(5) 0.0018(5) -0.0008(6) N1 0.0209(6) 0.0170(7) 0.0132(5) -0.0010(5) 0.0011(5) -0.0005(5) C1S 0.050(3) 0.066(4) 0.029(2) 0.014(2) 0.004(2) 0.018(3) Cl1S 0.0316(7) 0.1014(16) 0.0775(11) -0.0367(11) 0.0036(6) -0.0035(8) O2 0.0225(6) 0.0263(7) 0.0205(6) 0.0055(5) 0.0024(5) -0.0052(5) C2 0.0256(8) 0.0195(8) 0.0190(7) -0.0023(6) 0.0060(6) -0.0024(7) Cl2S 0.0401(6) 0.0698(10) 0.0526(7) -0.0016(7) 0.0176(6) 0.0022(6) C3 0.0274(9) 0.0203(9) 0.0237(8) 0.0001(6) 0.0111(7) 0.0028(7) Cl3S 0.0892(14) 0.0557(10) 0.0514(8) 0.0052(7) 0.0127(8) 0.0136(9) C4 0.0215(8) 0.0252(9) 0.0170(7) 0.0037(6) 0.0071(6) 0.0005(7) C5 0.0220(8) 0.0214(9) 0.0153(6) -0.0011(6) 0.0038(6) -0.0042(6) C6 0.0220(8) 0.0187(8) 0.0147(6) -0.0012(6) 0.0043(5) -0.0009(6) C7 0.0240(9) 0.0379(12) 0.0303(9) 0.0048(8) 0.0137(7) 0.0012(8) C8 0.0204(8) 0.0174(8) 0.0173(7) -0.0022(6) 0.0017(6) -0.0013(6) C9 0.0174(7) 0.0158(8) 0.0152(6) -0.0013(5) 0.0039(5) -0.0024(6) C10 0.0164(7) 0.0174(8) 0.0143(6) 0.0002(5) 0.0053(5) -0.0015(6) C11 0.0163(7) 0.0159(7) 0.0127(6) -0.0001(5) 0.0040(5) -0.0008(6) C12 0.0201(7) 0.0174(8) 0.0133(6) -0.0015(5) 0.0023(5) 0.0002(6) C13 0.0157(7) 0.0206(8) 0.0128(6) 0.0007(5) 0.0058(5) 0.0006(6) C14 0.0192(7) 0.0222(9) 0.0174(7) 0.0033(6) 0.0051(6) -0.0022(6) C15 0.0176(7) 0.0338(10) 0.0191(7) 0.0001(7) 0.0045(6) -0.0035(7) C16 0.0198(8) 0.0374(11) 0.0164(7) 0.0024(7) 0.0037(6) 0.0062(7) C17 0.0287(9) 0.0255(10) 0.0213(8) 0.0057(7) 0.0076(7) 0.0063(7) C18 0.0220(8) 0.0194(9) 0.0210(7) 0.0029(6) 0.0072(6) 0.0010(6) C19 0.0176(7) 0.0178(8) 0.0131(6) -0.0021(5) 0.0051(5) -0.0028(6) C20 0.0224(8) 0.0315(10) 0.0252(8) -0.0109(7) 0.0126(7) -0.0081(7) C21 0.0276(9) 0.0406(13) 0.0324(9) -0.0144(9) 0.0138(8) 0.0019(9) C22 0.037(3) 0.022(2) 0.0205(19) -0.0041(16) 0.0133(18) -0.0055(19) C22' 0.037(2) 0.044(3) 0.0259(17) -0.0163(18) 0.0149(15) -0.0039(18) C23 0.031(2) 0.034(3) 0.0156(17) -0.0030(16) 0.0080(16) -0.001(2) C23' 0.032(2) 0.046(3) 0.0218(15) -0.0133(15) 0.0087(13) -0.0046(17) C24 0.0684(16) 0.0371(13) 0.0153(8) 0.0017(8) 0.0110(9) 0.0174(12) C25 0.0477(11) 0.0185(9) 0.0184(7) 0.0002(6) 0.0165(7) -0.0026(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.4310(14) . ? S1 O2 1.4369(15) . ? S1 N1 1.6282(14) . ? S1 C1 1.7645(18) . ? C1 C2 1.390(3) . ? C1 C6 1.397(2) . ? N1 C12 1.476(2) . ? N1 C8 1.484(2) . ? C1S Cl3S 1.708(7) . ? C1S Cl2S 1.745(6) . ? C1S Cl1S 1.815(7) . ? C2 C3 1.393(3) . ? C3 C4 1.393(3) . ? C4 C5 1.395(3) . ? C4 C7 1.506(3) . ? C5 C6 1.393(2) . ? C8 C9 1.515(2) . ? C9 C10 1.511(2) . ? C9 C11 1.516(2) . ? C10 C13 1.493(2) . ? C10 C11 1.522(2) . ? C11 C19 1.491(2) . ? C11 C12 1.518(2) . ? C13 C18 1.391(2) . ? C13 C14 1.398(2) . ? C14 C15 1.397(2) . ? C15 C16 1.386(3) . ? C16 C17 1.381(3) . ? C17 C18 1.401(2) . ? C19 C25 1.500(2) . ? C19 C20 1.507(2) . ? C20 C25 1.513(3) . ? C20 C21 1.521(3) . ? C21 C22 1.508(5) . ? C21 C22' 1.594(5) . ? C22 C23 1.533(7) . ? C22' C23' 1.518(6) . ? C23 C24 1.576(5) . ? C23' C24 1.567(5) . ? C24 C25 1.517(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 O1 S1 O2 120.25(9) . . ? O1 S1 N1 107.17(8) . . ? O2 S1 N1 106.32(8) . . ? O1 S1 C1 107.35(8) . . ? O2 S1 C1 107.53(9) . . ? N1 S1 C1 107.68(8) . . ? C2 C1 C6 120.75(16) . . ? C2 C1 S1 119.56(14) . . ? C6 C1 S1 119.67(14) . . ? C12 N1 C8 110.06(13) . . ? C12 N1 S1 119.68(12) . . ? C8 N1 S1 119.17(11) . . ? Cl3S C1S Cl2S 114.9(3) . . ? Cl3S C1S Cl1S 111.7(4) . . ? Cl2S C1S Cl1S 107.6(4) . . ? C1 C2 C3 119.11(17) . . ? C2 C3 C4 121.34(18) . . ? C3 C4 C5 118.51(17) . . ? C3 C4 C7 121.15(18) . . ? C5 C4 C7 120.32(18) . . ? C6 C5 C4 121.24(17) . . ? C5 C6 C1 119.01(17) . . ? N1 C8 C9 102.18(13) . . ? C10 C9 C8 115.41(14) . . ? C10 C9 C11 60.38(11) . . ? C8 C9 C11 107.96(14) . . ? C13 C10 C9 122.24(14) . . ? C13 C10 C11 118.66(13) . . ? C9 C10 C11 59.97(11) . . ? C19 C11 C9 125.13(14) . . ? C19 C11 C12 117.59(14) . . ? C9 C11 C12 106.93(13) . . ? C19 C11 C10 119.69(13) . . ? C9 C11 C10 59.65(11) . . ? C12 C11 C10 114.96(13) . . ? N1 C12 C11 102.89(14) . . ? C18 C13 C14 118.32(15) . . ? C18 C13 C10 123.07(16) . . ? C14 C13 C10 118.60(15) . . ? C15 C14 C13 120.97(17) . . ? C16 C15 C14 120.01(18) . . ? C17 C16 C15 119.62(16) . . ? C16 C17 C18 120.48(18) . . ? C13 C18 C17 120.59(18) . . ? C11 C19 C25 122.75(15) . . ? C11 C19 C20 121.79(14) . . ? C25 C19 C20 60.41(13) . . ? C19 C20 C25 59.56(12) . . ? C19 C20 C21 119.93(17) . . ? C25 C20 C21 119.97(16) . . ? C22 C21 C20 112.9(2) . . ? C22 C21 C22' 30.9(2) . . ? C20 C21 C22' 111.9(2) . . ? C21 C22 C23 104.8(4) . . ? C23' C22' C21 111.3(3) . . ? C22 C23 C24 110.0(3) . . ? C22' C23' C24 105.0(3) . . ? C25 C24 C23' 113.4(2) . . ? C25 C24 C23 109.4(2) . . ? C23' C24 C23 35.5(2) . . ? C19 C25 C20 60.04(12) . . ? C19 C25 C24 119.54(19) . . ? C20 C25 C24 120.32(17) . . ? 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 O1 S1 C1 C2 156.06(13) . . . . ? O2 S1 C1 C2 25.36(15) . . . . ? N1 S1 C1 C2 -88.84(15) . . . . ? O1 S1 C1 C6 -22.46(15) . . . . ? O2 S1 C1 C6 -153.17(13) . . . . ? N1 S1 C1 C6 92.63(14) . . . . ? O1 S1 N1 C12 -168.46(13) . . . . ? O2 S1 N1 C12 -38.68(16) . . . . ? C1 S1 N1 C12 76.32(15) . . . . ? O1 S1 N1 C8 51.16(15) . . . . ? O2 S1 N1 C8 -179.06(13) . . . . ? C1 S1 N1 C8 -64.06(15) . . . . ? C6 C1 C2 C3 1.4(2) . . . . ? S1 C1 C2 C3 -177.14(13) . . . . ? C1 C2 C3 C4 -0.3(3) . . . . ? C2 C3 C4 C5 -1.3(3) . . . . ? C2 C3 C4 C7 177.04(17) . . . . ? C3 C4 C5 C6 2.0(2) . . . . ? C7 C4 C5 C6 -176.35(16) . . . . ? C4 C5 C6 C1 -1.0(2) . . . . ? C2 C1 C6 C5 -0.7(2) . . . . ? S1 C1 C6 C5 177.82(12) . . . . ? C12 N1 C8 C9 31.31(18) . . . . ? S1 N1 C8 C9 175.17(12) . . . . ? N1 C8 C9 C10 46.86(19) . . . . ? N1 C8 C9 C11 -18.23(17) . . . . ? C8 C9 C10 C13 156.07(15) . . . . ? C11 C9 C10 C13 -106.88(17) . . . . ? C8 C9 C10 C11 -97.05(16) . . . . ? C10 C9 C11 C19 106.85(17) . . . . ? C8 C9 C11 C19 -143.61(16) . . . . ? C10 C9 C11 C12 -109.44(14) . . . . ? C8 C9 C11 C12 0.10(18) . . . . ? C8 C9 C11 C10 109.54(15) . . . . ? C13 C10 C11 C19 -3.0(2) . . . . ? C9 C10 C11 C19 -115.70(17) . . . . ? C13 C10 C11 C9 112.73(17) . . . . ? C13 C10 C11 C12 -151.55(15) . . . . ? C9 C10 C11 C12 95.72(15) . . . . ? C8 N1 C12 C11 -31.45(17) . . . . ? S1 N1 C12 C11 -175.10(11) . . . . ? C19 C11 C12 N1 165.13(14) . . . . ? C9 C11 C12 N1 18.23(17) . . . . ? C10 C11 C12 N1 -45.60(18) . . . . ? C9 C10 C13 C18 -28.9(2) . . . . ? C11 C10 C13 C18 -99.7(2) . . . . ? C9 C10 C13 C14 152.47(16) . . . . ? C11 C10 C13 C14 81.7(2) . . . . ? C18 C13 C14 C15 -0.5(3) . . . . ? C10 C13 C14 C15 178.18(16) . . . . ? C13 C14 C15 C16 0.8(3) . . . . ? C14 C15 C16 C17 -0.1(3) . . . . ? C15 C16 C17 C18 -0.9(3) . . . . ? C14 C13 C18 C17 -0.4(3) . . . . ? C10 C13 C18 C17 -179.09(16) . . . . ? C16 C17 C18 C13 1.2(3) . . . . ? C9 C11 C19 C25 -0.2(3) . . . . ? C12 C11 C19 C25 -140.47(18) . . . . ? C10 C11 C19 C25 71.8(2) . . . . ? C9 C11 C19 C20 72.8(2) . . . . ? C12 C11 C19 C20 -67.5(2) . . . . ? C10 C11 C19 C20 144.77(17) . . . . ? C11 C19 C20 C25 -112.33(19) . . . . ? C11 C19 C20 C21 138.38(19) . . . . ? C25 C19 C20 C21 -109.3(2) . . . . ? C19 C20 C21 C22 48.6(3) . . . . ? C25 C20 C21 C22 -21.4(4) . . . . ? C19 C20 C21 C22' 82.0(3) . . . . ? C25 C20 C21 C22' 12.0(3) . . . . ? C20 C21 C22 C23 56.1(4) . . . . ? C22' C21 C22 C23 -38.6(4) . . . . ? C22 C21 C22' C23' 49.4(5) . . . . ? C20 C21 C22' C23' -49.0(4) . . . . ? C21 C22 C23 C24 -74.9(5) . . . . ? C21 C22' C23' C24 70.2(4) . . . . ? C22' C23' C24 C25 -55.7(4) . . . . ? C22' C23' C24 C23 35.2(4) . . . . ? C22 C23 C24 C25 53.5(4) . . . . ? C22 C23 C24 C23' -49.9(4) . . . . ? C11 C19 C25 C20 110.80(18) . . . . ? C11 C19 C25 C24 -139.14(19) . . . . ? C20 C19 C25 C24 110.1(2) . . . . ? C21 C20 C25 C19 109.2(2) . . . . ? C19 C20 C25 C24 -108.8(2) . . . . ? C21 C20 C25 C24 0.4(3) . . . . ? C23' C24 C25 C19 -48.5(3) . . . . ? C23 C24 C25 C19 -86.5(3) . . . . ? C23' C24 C25 C20 22.0(3) . . . . ? C23 C24 C25 C20 -16.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 31.51 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 1.514 _refine_diff_density_min -0.781 _refine_diff_density_rms 0.081 # Attachment 'web_deposit_cif_file_1_AntonioM.Echavarren_1276529606.cif' # Attachment 'web_deposit_cif_file_1_AntonioM.Echavarren_1276529606.cif' data_nm087_0m _database_code_depnum_ccdc_archive 'CCDC 780816' #TrackingRef 'web_deposit_cif_file_1_AntonioM.Echavarren_1276529606.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H29 N O2 S' _chemical_formula_weight 443.58 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.9620(7) _cell_length_b 10.4716(7) _cell_length_c 12.3795(10) _cell_angle_alpha 90.00 _cell_angle_beta 100.903(3) _cell_angle_gamma 90.00 _cell_volume 1140.80(15) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5107 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 36.14 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.291 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.168 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.94 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details ; SADABS Version 2008/1 Bruker-Nonius Blessing, Acta Cryst. (1995) A51 33-38 ; _exptl_special_details ; It should be noted that the esd's of the cell dimensions are probably too low; they should be multiplied by a factor of 2 to 10 ; _diffrn_ambient_temperature 100(2) _diffrn_measurement_specimen_suppport 'magnetic support whith 10 micron nylon fiber cryoloop' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'rotating anode X-ray tube' _diffrn_source_type 'Bruker-Nonius FR 591' _diffrn_source_power 50 _diffrn_source_current 70 _diffrn_source_size '3 mm x 0.3 mm fine focus' _diffrn_radiation_monochromator 'Multilayer Montel 200 mirrors' _diffrn_detector_type '4K CCD area detector APEX II' _diffrn_measurement_device_type 'Kappa 4-axis goniometer bruker-nonius' _diffrn_measurement_method ; Fullsphere data collection, phi and omega scans ; _diffrn_detector_area_resol_mean 512 _diffrn_reflns_number 13699 _diffrn_reflns_av_R_equivalents 0.0306 _diffrn_reflns_av_sigmaI/netI 0.0416 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 36.43 _reflns_number_total 6325 _reflns_number_gt 5682 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 v2009.1-0' _computing_cell_refinement 'Bruker APEX2 v2009.1-0' _computing_data_reduction 'Bruker SAINT V7.60A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXS-97 (Sheldrick, 2008)' _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^)+(0.0855P)^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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _chemical_absolute_configuration ad _refine_ls_abs_structure_Flack 0.04(5) _refine_ls_number_reflns 6325 _refine_ls_number_parameters 291 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0493 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.1227 _refine_ls_wR_factor_gt 0.1153 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 C1 C 0.46930(19) 0.5719(2) 0.56317(15) 0.0262(3) Uani 1 1 d . . . H1A H 0.4920 0.5976 0.6407 0.039 Uiso 1 1 calc R . . H1B H 0.4254 0.4858 0.5571 0.039 Uiso 1 1 calc R . . H1C H 0.3966 0.6320 0.5215 0.039 Uiso 1 1 calc R . . C2 C 0.61342(16) 0.57215(18) 0.51752(12) 0.0188(3) Uani 1 1 d . . . C3 C 0.6782(2) 0.45853(16) 0.48907(15) 0.0200(3) Uani 1 1 d . . . H3 H 0.6294 0.3797 0.4980 0.024 Uiso 1 1 calc R . . C4 C 0.8120(2) 0.45818(14) 0.44820(13) 0.0185(3) Uani 1 1 d . . . H4 H 0.8548 0.3801 0.4295 0.022 Uiso 1 1 calc R . . C5 C 0.88273(15) 0.57419(15) 0.43493(10) 0.0141(2) Uani 1 1 d . . . C6 C 0.8211(2) 0.68958(15) 0.46254(13) 0.0171(3) Uani 1 1 d . . . H6 H 0.8700 0.7682 0.4534 0.021 Uiso 1 1 calc R . . C7 C 0.6874(2) 0.68753(15) 0.50342(14) 0.0183(3) Uani 1 1 d . . . H7 H 0.6450 0.7657 0.5223 0.022 Uiso 1 1 calc R . . C8 C 0.95770(18) 0.70905(14) 0.19865(12) 0.0159(3) Uani 1 1 d . . . H8A H 1.0390 0.7742 0.2140 0.019 Uiso 1 1 calc R . . H8B H 0.8662 0.7411 0.2240 0.019 Uiso 1 1 calc R . . C9 C 0.92206(17) 0.67425(14) 0.07693(12) 0.0143(3) Uani 1 1 d . . . C10 C 0.90983(18) 0.53028(14) 0.07024(12) 0.0152(3) Uani 1 1 d . . . H10 H 0.8334 0.4901 0.0106 0.018 Uiso 1 1 calc R . . C11 C 0.9290(2) 0.47923(14) 0.18675(12) 0.0170(3) Uani 1 1 d . . . H11A H 0.8296 0.4619 0.2075 0.020 Uiso 1 1 calc R . . H11B H 0.9911 0.4004 0.1962 0.020 Uiso 1 1 calc R . . C12 C 1.04813(17) 0.59459(13) 0.04165(11) 0.0148(3) Uani 1 1 d . . . H12 H 1.1419 0.5862 0.0996 0.018 Uiso 1 1 calc R . . C13 C 1.07809(18) 0.60287(14) -0.07250(12) 0.0154(3) Uani 1 1 d . . . C14 C 1.20813(19) 0.66827(16) -0.08866(14) 0.0201(3) Uani 1 1 d . . . H14 H 1.2729 0.7065 -0.0276 0.024 Uiso 1 1 calc R . . C15 C 1.2442(2) 0.67810(19) -0.19335(16) 0.0247(3) Uani 1 1 d . . . H15 H 1.3329 0.7228 -0.2032 0.030 Uiso 1 1 calc R . . C16 C 1.1496(2) 0.6221(2) -0.28351(15) 0.0265(4) Uani 1 1 d . . . H16 H 1.1737 0.6285 -0.3548 0.032 Uiso 1 1 calc R . . C17 C 1.0212(2) 0.55758(19) -0.26851(14) 0.0253(4) Uani 1 1 d . . . H17 H 0.9564 0.5197 -0.3298 0.030 Uiso 1 1 calc R . . C18 C 0.9857(2) 0.54742(16) -0.16372(13) 0.0208(3) Uani 1 1 d . . . H18 H 0.8972 0.5020 -0.1545 0.025 Uiso 1 1 calc R . . C19 C 0.83648(18) 0.76767(14) -0.00301(12) 0.0156(3) Uani 1 1 d . . . H19 H 0.9032 0.8348 -0.0263 0.019 Uiso 1 1 calc R . . C20 C 0.70501(18) 0.73218(15) -0.09241(12) 0.0177(3) Uani 1 1 d . . . H20 H 0.6691 0.6420 -0.0898 0.021 Uiso 1 1 calc R . . C21 C 0.67622(18) 0.81651(15) 0.00128(13) 0.0172(3) Uani 1 1 d . . . H21 H 0.6612 0.9084 -0.0201 0.021 Uiso 1 1 calc R . . C22 C 0.6935(2) 0.78680(18) -0.20633(14) 0.0227(3) Uani 1 1 d . . . H22A H 0.5869 0.7868 -0.2440 0.034 Uiso 1 1 calc R . . H22B H 0.7536 0.7346 -0.2480 0.034 Uiso 1 1 calc R . . H22C H 0.7324 0.8745 -0.2011 0.034 Uiso 1 1 calc R . . C23 C 0.58525(18) 0.77623(16) 0.08359(13) 0.0188(3) Uani 1 1 d . . . C24 C 0.5700(2) 0.64850(17) 0.11462(15) 0.0225(3) Uani 1 1 d . . . H24 H 0.6178 0.5828 0.0805 0.027 Uiso 1 1 calc R . . C25 C 0.4860(2) 0.6166(2) 0.19468(16) 0.0288(4) Uani 1 1 d . . . H25 H 0.4796 0.5301 0.2166 0.035 Uiso 1 1 calc R . . C26 C 0.4108(2) 0.7123(3) 0.24284(17) 0.0340(5) Uani 1 1 d . . . H26 H 0.3526 0.6910 0.2969 0.041 Uiso 1 1 calc R . . C27 C 0.4221(2) 0.8375(2) 0.21109(17) 0.0327(4) Uani 1 1 d . . . H27 H 0.3694 0.9023 0.2424 0.039 Uiso 1 1 calc R . . C28 C 0.5101(2) 0.8703(2) 0.13331(16) 0.0259(4) Uani 1 1 d . . . H28 H 0.5191 0.9574 0.1140 0.031 Uiso 1 1 calc R . . N1 N 1.00852(15) 0.58612(12) 0.25095(10) 0.0153(2) Uani 1 1 d . . . O1 O 1.13371(14) 0.69088(12) 0.42094(10) 0.0185(2) Uani 1 1 d . . . O2 O 1.12578(15) 0.45368(11) 0.40791(10) 0.0201(2) Uani 1 1 d . . . S1 S 1.05315(4) 0.57558(3) 0.38389(3) 0.01422(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0200(7) 0.0288(7) 0.0306(8) 0.0009(8) 0.0073(6) -0.0010(7) C2 0.0183(6) 0.0212(6) 0.0167(6) 0.0004(6) 0.0032(5) -0.0001(6) C3 0.0220(8) 0.0176(6) 0.0212(7) 0.0005(5) 0.0065(6) -0.0025(5) C4 0.0243(8) 0.0133(6) 0.0184(7) -0.0013(5) 0.0051(6) -0.0013(5) C5 0.0179(5) 0.0140(5) 0.0111(5) 0.0003(5) 0.0042(4) 0.0006(5) C6 0.0220(7) 0.0146(6) 0.0156(6) -0.0010(4) 0.0059(5) -0.0005(5) C7 0.0214(7) 0.0177(6) 0.0167(6) -0.0006(5) 0.0055(6) 0.0008(5) C8 0.0219(7) 0.0133(5) 0.0131(6) 0.0004(4) 0.0047(5) 0.0015(5) C9 0.0177(6) 0.0132(5) 0.0125(6) -0.0003(4) 0.0045(5) 0.0004(4) C10 0.0196(7) 0.0142(5) 0.0125(6) -0.0002(4) 0.0045(5) -0.0009(5) C11 0.0228(7) 0.0143(6) 0.0143(6) -0.0009(4) 0.0046(5) -0.0019(5) C12 0.0172(6) 0.0156(6) 0.0120(5) 0.0002(4) 0.0040(5) 0.0007(4) C13 0.0186(6) 0.0160(6) 0.0125(6) 0.0011(4) 0.0056(5) 0.0042(4) C14 0.0193(7) 0.0231(7) 0.0186(7) 0.0024(5) 0.0057(6) 0.0015(5) C15 0.0233(8) 0.0294(8) 0.0242(8) 0.0062(6) 0.0116(6) 0.0033(6) C16 0.0318(9) 0.0340(9) 0.0171(7) 0.0050(6) 0.0131(7) 0.0085(7) C17 0.0319(8) 0.0307(9) 0.0139(6) -0.0011(6) 0.0058(6) 0.0014(7) C18 0.0236(7) 0.0252(7) 0.0143(6) -0.0028(5) 0.0052(6) -0.0013(5) C19 0.0184(6) 0.0144(5) 0.0145(6) 0.0014(4) 0.0043(5) -0.0010(5) C20 0.0205(7) 0.0188(6) 0.0139(6) 0.0007(5) 0.0035(5) -0.0011(5) C21 0.0184(7) 0.0170(6) 0.0168(6) 0.0007(5) 0.0051(5) 0.0015(5) C22 0.0250(8) 0.0280(8) 0.0149(6) 0.0040(5) 0.0031(6) 0.0024(6) C23 0.0167(7) 0.0230(6) 0.0163(6) -0.0013(5) 0.0024(5) -0.0007(5) C24 0.0208(7) 0.0248(7) 0.0223(7) 0.0021(6) 0.0046(6) -0.0016(6) C25 0.0218(8) 0.0392(10) 0.0252(8) 0.0068(7) 0.0041(7) -0.0073(7) C26 0.0218(8) 0.0614(14) 0.0204(8) -0.0030(8) 0.0080(7) -0.0081(9) C27 0.0232(9) 0.0501(12) 0.0264(9) -0.0126(8) 0.0086(7) 0.0001(8) C28 0.0224(8) 0.0312(9) 0.0249(8) -0.0067(6) 0.0063(7) 0.0007(6) N1 0.0235(5) 0.0127(5) 0.0103(4) 0.0002(4) 0.0044(4) -0.0007(4) O1 0.0208(5) 0.0198(5) 0.0152(5) -0.0028(4) 0.0041(4) -0.0036(4) O2 0.0248(6) 0.0191(5) 0.0172(5) 0.0040(4) 0.0063(5) 0.0067(4) S1 0.01817(15) 0.01430(13) 0.01060(13) 0.00058(11) 0.00378(11) 0.00073(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 C1 C2 1.505(2) . ? C2 C3 1.398(2) . ? C2 C7 1.405(2) . ? C3 C4 1.387(3) . ? C4 C5 1.394(2) . ? C5 C6 1.398(2) . ? C5 S1 1.7599(15) . ? C6 C7 1.386(3) . ? C8 N1 1.4738(19) . ? C8 C9 1.524(2) . ? C9 C19 1.496(2) . ? C9 C10 1.513(2) . ? C9 C12 1.533(2) . ? C10 C12 1.510(2) . ? C10 C11 1.517(2) . ? C11 N1 1.4757(19) . ? C12 C13 1.490(2) . ? C13 C18 1.394(2) . ? C13 C14 1.398(2) . ? C14 C15 1.397(3) . ? C15 C16 1.396(3) . ? C16 C17 1.377(3) . ? C17 C18 1.397(2) . ? C19 C20 1.5027(19) . ? C19 C21 1.535(2) . ? C20 C22 1.507(2) . ? C20 C21 1.518(2) . ? C21 C23 1.482(3) . ? C23 C28 1.400(3) . ? C23 C24 1.405(2) . ? C24 C25 1.394(3) . ? C25 C26 1.402(3) . ? C26 C27 1.378(4) . ? C27 C28 1.398(3) . ? N1 S1 1.6222(12) . ? O1 S1 1.4368(12) . ? O2 S1 1.4381(12) . ? 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 C3 C2 C7 118.18(15) . . ? C3 C2 C1 121.32(17) . . ? C7 C2 C1 120.49(16) . . ? C4 C3 C2 121.54(15) . . ? C3 C4 C5 118.98(15) . . ? C4 C5 C6 120.98(14) . . ? C4 C5 S1 119.63(13) . . ? C6 C5 S1 119.39(13) . . ? C7 C6 C5 119.01(15) . . ? C6 C7 C2 121.31(15) . . ? N1 C8 C9 102.42(12) . . ? C19 C9 C10 126.35(12) . . ? C19 C9 C8 118.89(13) . . ? C10 C9 C8 106.97(12) . . ? C19 C9 C12 118.73(13) . . ? C10 C9 C12 59.45(10) . . ? C8 C9 C12 112.57(12) . . ? C12 C10 C9 60.94(10) . . ? C12 C10 C11 115.42(12) . . ? C9 C10 C11 107.76(12) . . ? N1 C11 C10 101.61(12) . . ? C13 C12 C10 123.46(12) . . ? C13 C12 C9 120.89(11) . . ? C10 C12 C9 59.61(10) . . ? C18 C13 C14 118.13(15) . . ? C18 C13 C12 123.91(15) . . ? C14 C13 C12 117.95(13) . . ? C15 C14 C13 120.92(15) . . ? C16 C15 C14 119.91(18) . . ? C17 C16 C15 119.64(17) . . ? C16 C17 C18 120.37(15) . . ? C13 C18 C17 121.03(16) . . ? C9 C19 C20 123.92(13) . . ? C9 C19 C21 124.13(14) . . ? C20 C19 C21 59.96(10) . . ? C19 C20 C22 120.05(14) . . ? C19 C20 C21 61.08(10) . . ? C22 C20 C21 120.17(14) . . ? C23 C21 C20 123.71(14) . . ? C23 C21 C19 124.69(13) . . ? C20 C21 C19 58.97(10) . . ? C28 C23 C24 118.04(18) . . ? C28 C23 C21 118.36(16) . . ? C24 C23 C21 123.60(16) . . ? C25 C24 C23 121.04(19) . . ? C24 C25 C26 119.9(2) . . ? C27 C26 C25 119.5(2) . . ? C26 C27 C28 120.7(2) . . ? C27 C28 C23 120.7(2) . . ? C8 N1 C11 110.38(11) . . ? C8 N1 S1 120.10(10) . . ? C11 N1 S1 119.73(10) . . ? O1 S1 O2 119.96(7) . . ? O1 S1 N1 106.22(7) . . ? O2 S1 N1 106.58(7) . . ? O1 S1 C5 108.07(8) . . ? O2 S1 C5 107.94(8) . . ? N1 S1 C5 107.49(7) . . ? 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 C7 C2 C3 C4 0.1(2) . . . . ? C1 C2 C3 C4 -179.22(14) . . . . ? C2 C3 C4 C5 -0.3(2) . . . . ? C3 C4 C5 C6 0.2(2) . . . . ? C3 C4 C5 S1 179.65(11) . . . . ? C4 C5 C6 C7 -0.1(2) . . . . ? S1 C5 C6 C7 -179.53(11) . . . . ? C5 C6 C7 C2 0.0(2) . . . . ? C3 C2 C7 C6 0.0(2) . . . . ? C1 C2 C7 C6 179.34(14) . . . . ? N1 C8 C9 C19 167.60(14) . . . . ? N1 C8 C9 C10 16.42(16) . . . . ? N1 C8 C9 C12 -46.93(16) . . . . ? C19 C9 C10 C12 104.99(18) . . . . ? C8 C9 C10 C12 -106.61(13) . . . . ? C19 C9 C10 C11 -145.27(16) . . . . ? C8 C9 C10 C11 3.13(18) . . . . ? C12 C9 C10 C11 109.74(13) . . . . ? C12 C10 C11 N1 44.38(17) . . . . ? C9 C10 C11 N1 -21.26(17) . . . . ? C9 C10 C12 C13 -109.01(15) . . . . ? C11 C10 C12 C13 153.97(13) . . . . ? C11 C10 C12 C9 -97.02(14) . . . . ? C19 C9 C12 C13 -4.3(2) . . . . ? C10 C9 C12 C13 113.20(15) . . . . ? C8 C9 C12 C13 -149.81(13) . . . . ? C19 C9 C12 C10 -117.48(14) . . . . ? C8 C9 C12 C10 96.99(14) . . . . ? C10 C12 C13 C18 -3.0(2) . . . . ? C9 C12 C13 C18 -74.87(19) . . . . ? C10 C12 C13 C14 178.16(13) . . . . ? C9 C12 C13 C14 106.30(17) . . . . ? C18 C13 C14 C15 0.2(2) . . . . ? C12 C13 C14 C15 179.09(14) . . . . ? C13 C14 C15 C16 0.0(3) . . . . ? C14 C15 C16 C17 0.0(3) . . . . ? C15 C16 C17 C18 -0.3(3) . . . . ? C14 C13 C18 C17 -0.4(2) . . . . ? C12 C13 C18 C17 -179.27(15) . . . . ? C16 C17 C18 C13 0.5(3) . . . . ? C10 C9 C19 C20 10.9(3) . . . . ? C8 C9 C19 C20 -134.16(17) . . . . ? C12 C9 C19 C20 82.5(2) . . . . ? C10 C9 C19 C21 85.1(2) . . . . ? C8 C9 C19 C21 -60.0(2) . . . . ? C12 C9 C19 C21 156.64(13) . . . . ? C9 C19 C20 C22 -136.81(17) . . . . ? C21 C19 C20 C22 110.10(17) . . . . ? C9 C19 C20 C21 113.09(18) . . . . ? C19 C20 C21 C23 -113.39(16) . . . . ? C22 C20 C21 C23 136.69(16) . . . . ? C22 C20 C21 C19 -109.92(17) . . . . ? C9 C19 C21 C23 -1.0(2) . . . . ? C20 C19 C21 C23 111.79(17) . . . . ? C9 C19 C21 C20 -112.75(16) . . . . ? C20 C21 C23 C28 -152.12(14) . . . . ? C19 C21 C23 C28 134.85(16) . . . . ? C20 C21 C23 C24 27.8(2) . . . . ? C19 C21 C23 C24 -45.2(2) . . . . ? C28 C23 C24 C25 -1.7(2) . . . . ? C21 C23 C24 C25 178.35(14) . . . . ? C23 C24 C25 C26 2.2(2) . . . . ? C24 C25 C26 C27 -0.6(3) . . . . ? C25 C26 C27 C28 -1.4(3) . . . . ? C26 C27 C28 C23 1.9(3) . . . . ? C24 C23 C28 C27 -0.3(2) . . . . ? C21 C23 C28 C27 179.65(15) . . . . ? C9 C8 N1 C11 -31.78(17) . . . . ? C9 C8 N1 S1 -177.58(11) . . . . ? C10 C11 N1 C8 33.52(17) . . . . ? C10 C11 N1 S1 179.46(11) . . . . ? C8 N1 S1 O1 -39.72(14) . . . . ? C11 N1 S1 O1 177.64(12) . . . . ? C8 N1 S1 O2 -168.72(12) . . . . ? C11 N1 S1 O2 48.65(14) . . . . ? C8 N1 S1 C5 75.76(13) . . . . ? C11 N1 S1 C5 -66.87(14) . . . . ? C4 C5 S1 O1 -155.75(11) . . . . ? C6 C5 S1 O1 23.66(12) . . . . ? C4 C5 S1 O2 -24.62(13) . . . . ? C6 C5 S1 O2 154.79(11) . . . . ? C4 C5 S1 N1 89.99(12) . . . . ? C6 C5 S1 N1 -90.59(12) . . . . ? _diffrn_measured_fraction_theta_max 0.879 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.952 _refine_diff_density_max 0.733 _refine_diff_density_min -0.401 _refine_diff_density_rms 0.068 # Attachment 'web_deposit_cif_file_2_AntonioM.Echavarren_1276529606.cif' data_ppg767_0m _database_code_depnum_ccdc_archive 'CCDC 780817' #TrackingRef 'web_deposit_cif_file_2_AntonioM.Echavarren_1276529606.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H27 N O2 S' _chemical_formula_weight 429.56 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 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 13.6368(12) _cell_length_b 7.9693(8) _cell_length_c 21.2530(17) _cell_angle_alpha 90.00 _cell_angle_beta 97.724(2) _cell_angle_gamma 90.00 _cell_volume 2288.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9834 _cell_measurement_theta_min 2.73 _cell_measurement_theta_max 33.16 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.60 _exptl_crystal_size_min 0.60 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.165 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9998 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details ; SADABS Version 2008/1 Bruker-Nonius Blessing, Acta Cryst. (1995) A51 33-38 ; _exptl_special_details ; It should be noted that the esd's of the cell dimensions are probably too low; they should be multiplied by a factor of 2 to 10 ; _diffrn_ambient_temperature 100(2) _diffrn_measurement_specimen_suppport 'magnetic support whith 10 micron nylon fiber cryoloop' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'rotating anode X-ray tube' _diffrn_source_type 'Bruker-Nonius FR 591' _diffrn_source_power 50 _diffrn_source_current 70 _diffrn_source_size '3 mm x 0.3 mm fine focus' _diffrn_radiation_monochromator 'Multilayer Montel 200 mirrors' _diffrn_detector_type '4K CCD area detector APEX II' _diffrn_measurement_device_type 'Kappa 4-axis goniometer bruker-nonius' _diffrn_measurement_method ; Fullsphere data collection, phi and omega scans ; _diffrn_detector_area_resol_mean 512 _diffrn_reflns_number 21425 _diffrn_reflns_av_R_equivalents 0.0234 _diffrn_reflns_av_sigmaI/netI 0.0303 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 33.17 _reflns_number_total 8536 _reflns_number_gt 7333 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 v2009.1-0' _computing_cell_refinement 'Bruker APEX2 v2009.1-0' _computing_data_reduction 'Bruker SAINT V7.60A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXS-97 (Sheldrick, 2008)' _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^)+(0.0621P)^2^+1.0488P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8536 _refine_ls_number_parameters 281 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0563 _refine_ls_R_factor_gt 0.0483 _refine_ls_wR_factor_ref 0.1393 _refine_ls_wR_factor_gt 0.1327 _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_restrained_S_all 1.109 _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 C1 C 0.48204(10) -0.19154(18) 0.23052(7) 0.0285(3) Uani 1 1 d . . . H1 H 0.5385 -0.2556 0.2240 0.034 Uiso 1 1 calc R . . C2 C 0.44895(10) -0.19057(17) 0.28937(7) 0.0279(3) Uani 1 1 d . . . H2 H 0.4829 -0.2541 0.3234 0.034 Uiso 1 1 calc R . . C3 C 0.36597(9) -0.09669(16) 0.29883(6) 0.0228(2) Uani 1 1 d . . . H3 H 0.3436 -0.0970 0.3393 0.027 Uiso 1 1 calc R . . C4 C 0.31529(8) -0.00209(14) 0.24950(6) 0.0179(2) Uani 1 1 d . . . C5 C 0.34923(9) -0.00432(16) 0.19035(6) 0.0207(2) Uani 1 1 d . . . H5 H 0.3155 0.0588 0.1562 0.025 Uiso 1 1 calc R . . C6 C 0.43204(9) -0.09816(17) 0.18108(7) 0.0252(2) Uani 1 1 d . . . H6 H 0.4546 -0.0984 0.1407 0.030 Uiso 1 1 calc R . . C7 C 0.23026(8) 0.10325(15) 0.26233(6) 0.0184(2) Uani 1 1 d . . . H7 H 0.2091 0.0856 0.3051 0.022 Uiso 1 1 calc R . . C8 C 0.14778(8) 0.15350(16) 0.21108(6) 0.0210(2) Uani 1 1 d . . . H8A H 0.1517 0.1142 0.1673 0.025 Uiso 1 1 calc R . . H8B H 0.0799 0.1598 0.2226 0.025 Uiso 1 1 calc R . . C9 C 0.22111(8) 0.28356(14) 0.23843(5) 0.01672(19) Uani 1 1 d . . . H9 H 0.2707 0.3164 0.2100 0.020 Uiso 1 1 calc R . . C10 C 0.19704(7) 0.41796(14) 0.28251(5) 0.01545(18) Uani 1 1 d . . . C11 C 0.12952(8) 0.56558(14) 0.26005(5) 0.01612(18) Uani 1 1 d . . . H11 H 0.1519 0.6760 0.2793 0.019 Uiso 1 1 calc R . . C12 C 0.08050(8) 0.57652(15) 0.19323(5) 0.0181(2) Uani 1 1 d . . . C13 C 0.11910(10) 0.69075(18) 0.15309(6) 0.0255(2) Uani 1 1 d . . . H13 H 0.1753 0.7561 0.1689 0.031 Uiso 1 1 calc R . . C14 C 0.07616(12) 0.7098(2) 0.09038(7) 0.0366(4) Uani 1 1 d . . . H14 H 0.1032 0.7877 0.0635 0.044 Uiso 1 1 calc R . . C15 C -0.00579(13) 0.6155(2) 0.06707(7) 0.0385(4) Uani 1 1 d . . . H15 H -0.0349 0.6285 0.0242 0.046 Uiso 1 1 calc R . . C16 C -0.04558(12) 0.5021(2) 0.10609(7) 0.0354(3) Uani 1 1 d . . . H16 H -0.1020 0.4375 0.0900 0.042 Uiso 1 1 calc R . . C17 C -0.00250(9) 0.48303(17) 0.16920(6) 0.0249(2) Uani 1 1 d . . . H17 H -0.0301 0.4056 0.1959 0.030 Uiso 1 1 calc R . . C18 C 0.09891(8) 0.43991(15) 0.30686(5) 0.01716(19) Uani 1 1 d . . . H18 H 0.0438 0.3599 0.2928 0.021 Uiso 1 1 calc R . . C19 C 0.11905(8) 0.48980(16) 0.37590(5) 0.0198(2) Uani 1 1 d . . . H19A H 0.0727 0.5781 0.3862 0.024 Uiso 1 1 calc R . . H19B H 0.1142 0.3921 0.4041 0.024 Uiso 1 1 calc R . . C20 C 0.27709(8) 0.46023(16) 0.33718(5) 0.0182(2) Uani 1 1 d . . . H20A H 0.3074 0.3572 0.3573 0.022 Uiso 1 1 calc R . . H20B H 0.3295 0.5306 0.3227 0.022 Uiso 1 1 calc R . . C21 C 0.30015(9) 0.41452(16) 0.49441(6) 0.0201(2) Uani 1 1 d . . . C22 C 0.39200(9) 0.33666(17) 0.49660(6) 0.0239(2) Uani 1 1 d . . . H22 H 0.4424 0.3854 0.4757 0.029 Uiso 1 1 calc R . . C23 C 0.40916(10) 0.18685(18) 0.52972(7) 0.0269(3) Uani 1 1 d . . . H23 H 0.4723 0.1351 0.5321 0.032 Uiso 1 1 calc R . . C24 C 0.33566(10) 0.11082(17) 0.55958(6) 0.0248(2) Uani 1 1 d . . . C25 C 0.35593(12) -0.0515(2) 0.59502(8) 0.0325(3) Uani 1 1 d . . . H25A H 0.3614 -0.0303 0.6408 0.049 Uiso 1 1 calc R . . H25B H 0.4180 -0.0997 0.5849 0.049 Uiso 1 1 calc R . . H25C H 0.3016 -0.1302 0.5825 0.049 Uiso 1 1 calc R . . C26 C 0.24356(10) 0.19013(18) 0.55624(6) 0.0250(2) Uani 1 1 d . . . H26 H 0.1926 0.1397 0.5761 0.030 Uiso 1 1 calc R . . C27 C 0.22552(9) 0.34152(18) 0.52430(6) 0.0229(2) Uani 1 1 d . . . H27 H 0.1630 0.3949 0.5228 0.027 Uiso 1 1 calc R . . N1 N 0.22193(7) 0.55393(14) 0.38137(5) 0.01822(18) Uani 1 1 d . . . O1 O 0.20741(8) 0.69905(13) 0.48112(5) 0.0272(2) Uani 1 1 d . . . O2 O 0.37146(7) 0.67380(13) 0.44287(5) 0.02542(19) Uani 1 1 d . . . S1 S 0.27750(2) 0.60289(4) 0.451504(13) 0.01963(7) 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 C1 0.0221(5) 0.0193(6) 0.0430(7) -0.0057(5) 0.0008(5) 0.0046(4) C2 0.0251(5) 0.0181(6) 0.0381(7) 0.0025(5) -0.0047(5) 0.0045(4) C3 0.0238(5) 0.0167(5) 0.0270(5) 0.0029(4) -0.0003(4) 0.0001(4) C4 0.0169(4) 0.0123(5) 0.0239(5) -0.0004(4) 0.0002(4) -0.0011(3) C5 0.0208(5) 0.0163(5) 0.0245(5) -0.0028(4) 0.0009(4) 0.0016(4) C6 0.0240(5) 0.0198(6) 0.0322(6) -0.0069(5) 0.0057(5) 0.0014(4) C7 0.0173(4) 0.0150(5) 0.0229(5) 0.0005(4) 0.0030(4) 0.0002(4) C8 0.0168(4) 0.0182(5) 0.0270(5) -0.0035(4) -0.0009(4) 0.0007(4) C9 0.0164(4) 0.0140(5) 0.0197(4) -0.0006(4) 0.0024(3) 0.0004(3) C10 0.0131(4) 0.0147(5) 0.0186(4) -0.0001(4) 0.0025(3) 0.0002(3) C11 0.0156(4) 0.0137(5) 0.0193(4) -0.0004(4) 0.0031(3) 0.0006(3) C12 0.0186(4) 0.0167(5) 0.0193(4) -0.0009(4) 0.0033(4) 0.0049(4) C13 0.0250(5) 0.0279(6) 0.0251(5) 0.0057(5) 0.0091(4) 0.0063(5) C14 0.0428(8) 0.0450(9) 0.0244(6) 0.0103(6) 0.0131(5) 0.0197(7) C15 0.0494(9) 0.0443(9) 0.0201(5) -0.0039(6) -0.0017(5) 0.0268(7) C16 0.0377(7) 0.0312(8) 0.0324(7) -0.0111(6) -0.0134(6) 0.0129(6) C17 0.0249(5) 0.0202(6) 0.0275(6) -0.0024(4) -0.0042(4) 0.0031(4) C18 0.0141(4) 0.0182(5) 0.0194(4) 0.0002(4) 0.0035(3) -0.0011(3) C19 0.0159(4) 0.0244(6) 0.0196(5) 0.0000(4) 0.0048(3) -0.0013(4) C20 0.0142(4) 0.0199(5) 0.0206(5) -0.0019(4) 0.0024(3) 0.0006(4) C21 0.0206(5) 0.0201(5) 0.0189(5) -0.0002(4) -0.0004(4) -0.0009(4) C22 0.0201(5) 0.0228(6) 0.0285(6) 0.0005(5) 0.0019(4) -0.0010(4) C23 0.0213(5) 0.0238(6) 0.0340(6) 0.0018(5) -0.0015(4) 0.0002(4) C24 0.0258(5) 0.0221(6) 0.0246(5) 0.0007(4) -0.0038(4) -0.0032(4) C25 0.0356(7) 0.0242(7) 0.0352(7) 0.0064(5) -0.0044(5) -0.0033(5) C26 0.0248(5) 0.0282(7) 0.0212(5) 0.0027(5) 0.0003(4) -0.0043(5) C27 0.0208(5) 0.0276(6) 0.0199(5) 0.0003(4) 0.0016(4) -0.0003(4) N1 0.0157(4) 0.0208(5) 0.0181(4) -0.0022(3) 0.0022(3) -0.0002(3) O1 0.0320(5) 0.0251(5) 0.0247(4) -0.0056(4) 0.0048(3) 0.0057(4) O2 0.0246(4) 0.0235(5) 0.0268(4) 0.0004(4) -0.0015(3) -0.0065(3) S1 0.02107(13) 0.01824(14) 0.01907(12) -0.00201(9) 0.00085(9) -0.00035(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.386(2) . ? C1 C6 1.389(2) . ? C2 C3 1.3936(18) . ? C3 C4 1.3966(17) . ? C4 C5 1.3969(17) . ? C4 C7 1.4861(16) . ? C5 C6 1.3903(17) . ? C7 C8 1.5107(16) . ? C7 C9 1.5236(16) . ? C8 C9 1.5020(16) . ? C9 C10 1.4884(16) . ? C10 C18 1.5084(15) . ? C10 C20 1.5212(15) . ? C10 C11 1.5302(16) . ? C11 C12 1.4888(16) . ? C11 C18 1.5095(16) . ? C12 C17 1.3934(17) . ? C12 C13 1.3979(17) . ? C13 C14 1.390(2) . ? C14 C15 1.382(3) . ? C15 C16 1.386(3) . ? C16 C17 1.3984(19) . ? C18 C19 1.5094(16) . ? C19 N1 1.4829(15) . ? C20 N1 1.4816(15) . ? C21 C22 1.3930(17) . ? C21 C27 1.3969(17) . ? C21 S1 1.7621(13) . ? C22 C23 1.3897(19) . ? C23 C24 1.3949(19) . ? C24 C26 1.3993(19) . ? C24 C25 1.503(2) . ? C26 C27 1.3900(19) . ? N1 S1 1.6263(10) . ? O1 S1 1.4348(10) . ? O2 S1 1.4345(10) . ? 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 C1 C6 119.56(12) . . ? C1 C2 C3 120.17(12) . . ? C2 C3 C4 120.73(12) . . ? C3 C4 C5 118.58(11) . . ? C3 C4 C7 119.12(11) . . ? C5 C4 C7 122.24(10) . . ? C6 C5 C4 120.53(12) . . ? C1 C6 C5 120.43(13) . . ? C4 C7 C8 122.76(10) . . ? C4 C7 C9 120.17(10) . . ? C8 C7 C9 59.34(8) . . ? C9 C8 C7 60.76(8) . . ? C10 C9 C8 123.27(9) . . ? C10 C9 C7 118.95(9) . . ? C8 C9 C7 59.90(8) . . ? C9 C10 C18 125.47(9) . . ? C9 C10 C20 116.35(9) . . ? C18 C10 C20 106.91(9) . . ? C9 C10 C11 122.09(9) . . ? C18 C10 C11 59.57(7) . . ? C20 C10 C11 114.07(9) . . ? C12 C11 C18 122.62(10) . . ? C12 C11 C10 121.12(9) . . ? C18 C11 C10 59.50(7) . . ? C17 C12 C13 118.59(12) . . ? C17 C12 C11 123.84(11) . . ? C13 C12 C11 117.56(11) . . ? C14 C13 C12 120.77(14) . . ? C15 C14 C13 120.02(15) . . ? C14 C15 C16 120.19(13) . . ? C15 C16 C17 119.81(15) . . ? C12 C17 C16 120.62(14) . . ? C10 C18 C19 108.07(9) . . ? C10 C18 C11 60.93(7) . . ? C19 C18 C11 115.82(10) . . ? N1 C19 C18 102.33(9) . . ? N1 C20 C10 102.85(8) . . ? C22 C21 C27 120.41(12) . . ? C22 C21 S1 119.41(10) . . ? C27 C21 S1 120.15(9) . . ? C23 C22 C21 119.28(12) . . ? C22 C23 C24 121.41(12) . . ? C23 C24 C26 118.40(12) . . ? C23 C24 C25 120.44(13) . . ? C26 C24 C25 121.16(13) . . ? C27 C26 C24 121.04(12) . . ? C26 C27 C21 119.44(12) . . ? C20 N1 C19 109.40(9) . . ? C20 N1 S1 119.22(7) . . ? C19 N1 S1 118.29(8) . . ? O2 S1 O1 120.32(6) . . ? O2 S1 N1 106.94(5) . . ? O1 S1 N1 105.93(6) . . ? O2 S1 C21 107.72(6) . . ? O1 S1 C21 107.98(6) . . ? N1 S1 C21 107.31(6) . . ? 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 C6 C1 C2 C3 0.1(2) . . . . ? C1 C2 C3 C4 -0.2(2) . . . . ? C2 C3 C4 C5 0.35(18) . . . . ? C2 C3 C4 C7 -176.88(11) . . . . ? C3 C4 C5 C6 -0.34(18) . . . . ? C7 C4 C5 C6 176.81(11) . . . . ? C2 C1 C6 C5 -0.1(2) . . . . ? C4 C5 C6 C1 0.21(19) . . . . ? C3 C4 C7 C8 -155.09(11) . . . . ? C5 C4 C7 C8 27.78(17) . . . . ? C3 C4 C7 C9 134.02(12) . . . . ? C5 C4 C7 C9 -43.11(16) . . . . ? C4 C7 C8 C9 -108.26(12) . . . . ? C7 C8 C9 C10 -106.79(12) . . . . ? C4 C7 C9 C10 -133.66(11) . . . . ? C8 C7 C9 C10 113.82(11) . . . . ? C4 C7 C9 C8 112.52(12) . . . . ? C8 C9 C10 C18 1.65(17) . . . . ? C7 C9 C10 C18 -69.53(14) . . . . ? C8 C9 C10 C20 140.37(11) . . . . ? C7 C9 C10 C20 69.18(13) . . . . ? C8 C9 C10 C11 -71.65(15) . . . . ? C7 C9 C10 C11 -142.84(10) . . . . ? C9 C10 C11 C12 3.17(15) . . . . ? C18 C10 C11 C12 -112.04(12) . . . . ? C20 C10 C11 C12 151.82(10) . . . . ? C9 C10 C11 C18 115.21(11) . . . . ? C20 C10 C11 C18 -96.15(10) . . . . ? C18 C11 C12 C17 5.56(17) . . . . ? C10 C11 C12 C17 77.05(14) . . . . ? C18 C11 C12 C13 -176.12(10) . . . . ? C10 C11 C12 C13 -104.64(13) . . . . ? C17 C12 C13 C14 -0.52(19) . . . . ? C11 C12 C13 C14 -178.93(12) . . . . ? C12 C13 C14 C15 0.1(2) . . . . ? C13 C14 C15 C16 0.2(2) . . . . ? C14 C15 C16 C17 -0.1(2) . . . . ? C13 C12 C17 C16 0.61(18) . . . . ? C11 C12 C17 C16 178.91(12) . . . . ? C15 C16 C17 C12 -0.3(2) . . . . ? C9 C10 C18 C19 140.19(11) . . . . ? C20 C10 C18 C19 -1.63(13) . . . . ? C11 C10 C18 C19 -110.05(11) . . . . ? C9 C10 C18 C11 -109.76(12) . . . . ? C20 C10 C18 C11 108.41(10) . . . . ? C12 C11 C18 C10 109.58(11) . . . . ? C12 C11 C18 C19 -153.23(10) . . . . ? C10 C11 C18 C19 97.19(10) . . . . ? C10 C18 C19 N1 19.95(12) . . . . ? C11 C18 C19 N1 -45.85(12) . . . . ? C9 C10 C20 N1 -163.25(9) . . . . ? C18 C10 C20 N1 -17.43(12) . . . . ? C11 C10 C20 N1 46.21(12) . . . . ? C27 C21 C22 C23 -1.05(19) . . . . ? S1 C21 C22 C23 -179.09(10) . . . . ? C21 C22 C23 C24 1.5(2) . . . . ? C22 C23 C24 C26 -0.8(2) . . . . ? C22 C23 C24 C25 179.87(13) . . . . ? C23 C24 C26 C27 -0.4(2) . . . . ? C25 C24 C26 C27 178.97(13) . . . . ? C24 C26 C27 C21 0.79(19) . . . . ? C22 C21 C27 C26 -0.08(19) . . . . ? S1 C21 C27 C26 177.94(10) . . . . ? C10 C20 N1 C19 31.48(12) . . . . ? C10 C20 N1 S1 172.08(8) . . . . ? C18 C19 N1 C20 -32.36(12) . . . . ? C18 C19 N1 S1 -173.37(8) . . . . ? C20 N1 S1 O2 47.58(11) . . . . ? C19 N1 S1 O2 -175.25(9) . . . . ? C20 N1 S1 O1 177.06(9) . . . . ? C19 N1 S1 O1 -45.77(11) . . . . ? C20 N1 S1 C21 -67.77(10) . . . . ? C19 N1 S1 C21 69.39(10) . . . . ? C22 C21 S1 O2 -19.07(12) . . . . ? C27 C21 S1 O2 162.88(10) . . . . ? C22 C21 S1 O1 -150.44(10) . . . . ? C27 C21 S1 O1 31.52(12) . . . . ? C22 C21 S1 N1 95.77(11) . . . . ? C27 C21 S1 N1 -82.28(11) . . . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 33.17 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.546 _refine_diff_density_min -0.362 _refine_diff_density_rms 0.065 # Attachment 'web_deposit_cif_file_3_AntonioM.Echavarren_1276529606.cif' data_ppg744_0m _database_code_depnum_ccdc_archive 'CCDC 780818' #TrackingRef 'web_deposit_cif_file_3_AntonioM.Echavarren_1276529606.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H31 N O2 S' _chemical_formula_weight 505.65 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 52.0309(19) _cell_length_b 6.2004(2) _cell_length_c 16.2321(6) _cell_angle_alpha 90.00 _cell_angle_beta 98.150(2) _cell_angle_gamma 90.00 _cell_volume 5183.8(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9950 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 28.35 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.296 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2144 _exptl_absorpt_coefficient_mu 0.157 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9845 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details ; SADABS Version 2008/1 Bruker-Nonius Blessing, Acta Cryst. (1995) A51 33-38 ; _exptl_special_details ; It should be noted that the esd's of the cell dimensions are probably too low; they should be multiplied by a factor of 2 to 10 ; _diffrn_ambient_temperature 100(2) _diffrn_measurement_specimen_suppport 'magnetic support whith 10 micron nylon fiber cryoloop' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'rotating anode X-ray tube' _diffrn_source_type 'Bruker-Nonius FR 591' _diffrn_source_power 50 _diffrn_source_current 70 _diffrn_source_size '3 mm x 0.3 mm fine focus' _diffrn_radiation_monochromator 'Multilayer Montel 200 mirrors' _diffrn_detector_type '4K CCD area detector APEX II' _diffrn_measurement_device_type 'Kappa 4-axis goniometer bruker-nonius' _diffrn_measurement_method ; Fullsphere data collection, phi and omega scans ; _diffrn_detector_area_resol_mean 512 _diffrn_reflns_number 59966 _diffrn_reflns_av_R_equivalents 0.0453 _diffrn_reflns_av_sigmaI/netI 0.0197 _diffrn_reflns_limit_h_min -67 _diffrn_reflns_limit_h_max 67 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 0.79 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5942 _reflns_number_gt 5272 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 v2009.1-0' _computing_cell_refinement 'Bruker APEX2 v2009.1-0' _computing_data_reduction 'Bruker SAINT V7.60A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXS-97 (Sheldrick, 2008)' _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^)+(0.0675P)^2^+4.3252P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5942 _refine_ls_number_parameters 335 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0464 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.1219 _refine_ls_wR_factor_gt 0.1089 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.103 _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 C1 C 0.12834(3) 0.8560(3) 0.27885(9) 0.0281(3) Uani 1 1 d . . . H1 H 0.1203 0.9935 0.2791 0.034 Uiso 1 1 calc R . . C2 C 0.15138(3) 0.8162(3) 0.33197(10) 0.0348(4) Uani 1 1 d . . . H2 H 0.1589 0.9266 0.3682 0.042 Uiso 1 1 calc R . . C3 C 0.16329(3) 0.6178(3) 0.33212(10) 0.0362(4) Uani 1 1 d . . . H3 H 0.1791 0.5923 0.3678 0.043 Uiso 1 1 calc R . . C4 C 0.15220(3) 0.4553(3) 0.28015(10) 0.0338(4) Uani 1 1 d . . . H4 H 0.1603 0.3180 0.2805 0.041 Uiso 1 1 calc R . . C5 C 0.12909(3) 0.4941(3) 0.22728(9) 0.0273(3) Uani 1 1 d . . . H5 H 0.1215 0.3820 0.1921 0.033 Uiso 1 1 calc R . . C6 C 0.11703(3) 0.6954(3) 0.22539(8) 0.0226(3) Uani 1 1 d . . . C7 C 0.09217(3) 0.7297(2) 0.16799(8) 0.0199(3) Uani 1 1 d . . . H7 H 0.0770 0.6483 0.1838 0.024 Uiso 1 1 calc R . . C8 C 0.08524(3) 0.9448(2) 0.12720(8) 0.0206(3) Uani 1 1 d . . . H8 H 0.0991 1.0571 0.1377 0.025 Uiso 1 1 calc R . . C9 C 0.05811(3) 1.0310(2) 0.11575(8) 0.0213(3) Uani 1 1 d . . . C10 C 0.05344(3) 1.2396(3) 0.08578(10) 0.0279(3) Uani 1 1 d . . . H10 H 0.0676 1.3263 0.0746 0.034 Uiso 1 1 calc R . . C11 C 0.02839(3) 1.3236(3) 0.07188(10) 0.0345(4) Uani 1 1 d . . . H11 H 0.0256 1.4658 0.0507 0.041 Uiso 1 1 calc R . . C12 C 0.00752(3) 1.2008(3) 0.08873(10) 0.0349(4) Uani 1 1 d . . . H12 H -0.0096 1.2581 0.0795 0.042 Uiso 1 1 calc R . . C13 C 0.01185(3) 0.9940(3) 0.11907(11) 0.0360(4) Uani 1 1 d . . . H13 H -0.0023 0.9089 0.1310 0.043 Uiso 1 1 calc R . . C14 C 0.03693(3) 0.9090(3) 0.13233(10) 0.0296(3) Uani 1 1 d . . . H14 H 0.0396 0.7662 0.1529 0.036 Uiso 1 1 calc R . . C15 C 0.09192(2) 0.7541(2) 0.07465(8) 0.0186(3) Uani 1 1 d . . . H15 H 0.0764 0.6872 0.0407 0.022 Uiso 1 1 calc R . . C16 C 0.11607(2) 0.7430(2) 0.03410(8) 0.0185(3) Uani 1 1 d . . . C17 C 0.11437(3) 0.6551(2) -0.05510(8) 0.0192(3) Uani 1 1 d . . . H17 H 0.1262 0.7278 -0.0901 0.023 Uiso 1 1 calc R . . C18 C 0.08887(3) 0.5841(2) -0.10171(8) 0.0212(3) Uani 1 1 d . . . C19 C 0.07384(3) 0.7342(3) -0.15190(9) 0.0267(3) Uani 1 1 d . . . H19 H 0.0802 0.8767 -0.1565 0.032 Uiso 1 1 calc R . . C20 C 0.04974(3) 0.6778(3) -0.19527(9) 0.0301(3) Uani 1 1 d . . . H20 H 0.0398 0.7815 -0.2290 0.036 Uiso 1 1 calc R . . C21 C 0.04033(3) 0.4710(3) -0.18920(10) 0.0310(3) Uani 1 1 d . . . H21 H 0.0237 0.4331 -0.2178 0.037 Uiso 1 1 calc R . . C22 C 0.05521(3) 0.3191(3) -0.14126(11) 0.0329(4) Uani 1 1 d . . . H22 H 0.0489 0.1761 -0.1377 0.039 Uiso 1 1 calc R . . C23 C 0.07944(3) 0.3756(3) -0.09806(10) 0.0274(3) Uani 1 1 d . . . H23 H 0.0896 0.2700 -0.0658 0.033 Uiso 1 1 calc R . . C24 C 0.12814(3) 0.5280(2) 0.01735(8) 0.0203(3) Uani 1 1 d . . . H24 H 0.1199 0.3928 0.0347 0.024 Uiso 1 1 calc R . . C25 C 0.15730(3) 0.5510(2) 0.03568(8) 0.0210(3) Uani 1 1 d . . . H25A H 0.1640 0.5007 0.0926 0.025 Uiso 1 1 calc R . . H25B H 0.1661 0.4707 -0.0051 0.025 Uiso 1 1 calc R . . C26 C 0.13860(2) 0.9004(2) 0.05700(8) 0.0197(3) Uani 1 1 d . . . H26A H 0.1351 1.0404 0.0282 0.024 Uiso 1 1 calc R . . H26B H 0.1420 0.9253 0.1178 0.024 Uiso 1 1 calc R . . C27 C 0.20332(2) 0.8462(2) 0.14512(8) 0.0203(3) Uani 1 1 d . . . C28 C 0.20192(3) 1.0083(2) 0.20349(9) 0.0233(3) Uani 1 1 d . . . H28 H 0.1939 1.1421 0.1872 0.028 Uiso 1 1 calc R . . C29 C 0.21250(3) 0.9725(3) 0.28624(9) 0.0271(3) Uani 1 1 d . . . H29 H 0.2116 1.0830 0.3263 0.033 Uiso 1 1 calc R . . C30 C 0.22431(3) 0.7768(3) 0.31099(9) 0.0272(3) Uani 1 1 d . . . C31 C 0.23588(3) 0.7381(4) 0.40039(10) 0.0382(4) Uani 1 1 d . . . H31A H 0.2260 0.6252 0.4242 0.057 Uiso 1 1 calc R . . H31B H 0.2352 0.8716 0.4323 0.057 Uiso 1 1 calc R . . H31C H 0.2540 0.6923 0.4027 0.057 Uiso 1 1 calc R . . C32 C 0.22526(3) 0.6160(3) 0.25152(9) 0.0268(3) Uani 1 1 d . . . H32 H 0.2331 0.4815 0.2680 0.032 Uiso 1 1 calc R . . C33 C 0.21499(3) 0.6485(2) 0.16850(9) 0.0241(3) Uani 1 1 d . . . H33 H 0.2159 0.5381 0.1284 0.029 Uiso 1 1 calc R . . N1 N 0.16059(2) 0.78648(19) 0.02741(7) 0.0195(2) Uani 1 1 d . . . O1 O 0.20450(2) 0.76205(19) -0.01092(6) 0.0273(2) Uani 1 1 d . . . O2 O 0.18680(2) 1.11576(17) 0.02707(7) 0.0260(2) Uani 1 1 d . . . S1 S 0.189781(6) 0.88762(6) 0.04015(2) 0.01992(11) 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 C1 0.0303(7) 0.0350(9) 0.0192(6) -0.0017(6) 0.0039(5) -0.0048(6) C2 0.0302(8) 0.0529(11) 0.0209(7) 0.0007(7) 0.0018(6) -0.0122(7) C3 0.0236(7) 0.0639(13) 0.0208(7) 0.0147(7) 0.0028(6) -0.0053(7) C4 0.0311(8) 0.0448(10) 0.0270(7) 0.0160(7) 0.0090(6) 0.0072(7) C5 0.0309(7) 0.0305(8) 0.0211(7) 0.0036(6) 0.0060(6) -0.0012(6) C6 0.0223(6) 0.0303(8) 0.0161(6) 0.0025(5) 0.0055(5) -0.0027(6) C7 0.0218(6) 0.0215(7) 0.0168(6) -0.0009(5) 0.0043(5) -0.0026(5) C8 0.0221(6) 0.0199(7) 0.0205(6) -0.0021(5) 0.0059(5) -0.0025(5) C9 0.0241(6) 0.0237(7) 0.0169(6) -0.0031(5) 0.0051(5) 0.0004(5) C10 0.0325(7) 0.0242(8) 0.0279(7) 0.0006(6) 0.0068(6) 0.0006(6) C11 0.0415(9) 0.0299(9) 0.0318(8) 0.0020(7) 0.0040(7) 0.0099(7) C12 0.0284(7) 0.0472(10) 0.0288(8) -0.0013(7) 0.0030(6) 0.0113(7) C13 0.0247(7) 0.0466(11) 0.0376(9) 0.0058(8) 0.0077(6) -0.0008(7) C14 0.0264(7) 0.0306(8) 0.0323(8) 0.0056(6) 0.0056(6) -0.0004(6) C15 0.0205(6) 0.0192(7) 0.0165(6) -0.0004(5) 0.0037(5) -0.0017(5) C16 0.0210(6) 0.0189(7) 0.0158(6) -0.0007(5) 0.0028(5) 0.0008(5) C17 0.0207(6) 0.0211(7) 0.0160(6) -0.0015(5) 0.0032(5) 0.0014(5) C18 0.0214(6) 0.0269(7) 0.0157(6) -0.0035(5) 0.0044(5) 0.0014(5) C19 0.0261(7) 0.0321(8) 0.0220(7) 0.0038(6) 0.0032(5) -0.0005(6) C20 0.0248(7) 0.0427(9) 0.0224(7) 0.0027(6) 0.0020(5) 0.0039(6) C21 0.0204(6) 0.0448(10) 0.0275(7) -0.0109(7) 0.0024(5) -0.0001(6) C22 0.0280(7) 0.0305(8) 0.0399(9) -0.0097(7) 0.0036(6) -0.0044(6) C23 0.0265(7) 0.0267(8) 0.0282(7) -0.0046(6) 0.0015(6) 0.0011(6) C24 0.0237(6) 0.0186(7) 0.0183(6) -0.0004(5) 0.0021(5) 0.0017(5) C25 0.0234(6) 0.0193(7) 0.0201(6) 0.0007(5) 0.0018(5) 0.0028(5) C26 0.0193(6) 0.0192(7) 0.0210(6) -0.0010(5) 0.0043(5) 0.0014(5) C27 0.0171(6) 0.0237(7) 0.0199(6) 0.0033(5) 0.0017(5) 0.0001(5) C28 0.0200(6) 0.0248(8) 0.0250(7) 0.0014(6) 0.0030(5) 0.0005(5) C29 0.0223(6) 0.0356(9) 0.0236(7) -0.0041(6) 0.0040(5) -0.0032(6) C30 0.0161(6) 0.0435(9) 0.0218(7) 0.0056(6) 0.0020(5) -0.0017(6) C31 0.0271(7) 0.0646(13) 0.0219(7) 0.0078(8) 0.0003(6) 0.0013(8) C32 0.0209(6) 0.0329(8) 0.0269(7) 0.0097(6) 0.0036(5) 0.0051(6) C33 0.0219(6) 0.0263(8) 0.0241(7) 0.0026(6) 0.0034(5) 0.0037(5) N1 0.0181(5) 0.0202(6) 0.0201(5) 0.0000(4) 0.0026(4) 0.0020(4) O1 0.0244(5) 0.0359(6) 0.0229(5) 0.0013(4) 0.0083(4) 0.0034(4) O2 0.0250(5) 0.0237(6) 0.0288(5) 0.0081(4) 0.0025(4) -0.0002(4) S1 0.01901(16) 0.0229(2) 0.01801(17) 0.00366(12) 0.00325(12) 0.00152(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 C1 C6 1.395(2) . ? C1 C2 1.396(2) . ? C2 C3 1.378(3) . ? C3 C4 1.386(3) . ? C4 C5 1.396(2) . ? C5 C6 1.396(2) . ? C6 C7 1.4986(19) . ? C7 C8 1.510(2) . ? C7 C15 1.5209(17) . ? C8 C9 1.4961(19) . ? C8 C15 1.5267(19) . ? C9 C10 1.391(2) . ? C9 C14 1.394(2) . ? C10 C11 1.392(2) . ? C11 C12 1.385(3) . ? C12 C13 1.381(3) . ? C13 C14 1.395(2) . ? C15 C16 1.5006(17) . ? C16 C24 1.5147(19) . ? C16 C26 1.5301(19) . ? C16 C17 1.5379(18) . ? C17 C18 1.4972(18) . ? C17 C24 1.5094(19) . ? C18 C23 1.387(2) . ? C18 C19 1.400(2) . ? C19 C20 1.393(2) . ? C20 C21 1.381(3) . ? C21 C22 1.386(2) . ? C22 C23 1.398(2) . ? C24 C25 1.5109(18) . ? C25 N1 1.4784(18) . ? C26 N1 1.4814(16) . ? C27 C28 1.390(2) . ? C27 C33 1.396(2) . ? C27 S1 1.7679(14) . ? C28 C29 1.395(2) . ? C29 C30 1.394(2) . ? C30 C32 1.393(2) . ? C30 C31 1.509(2) . ? C32 C33 1.392(2) . ? N1 S1 1.6289(11) . ? O1 S1 1.4351(11) . ? O2 S1 1.4356(11) . ? 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 C1 C2 120.52(16) . . ? C3 C2 C1 120.38(16) . . ? C2 C3 C4 119.96(15) . . ? C3 C4 C5 119.82(17) . . ? C6 C5 C4 120.86(15) . . ? C1 C6 C5 118.44(14) . . ? C1 C6 C7 122.44(14) . . ? C5 C6 C7 119.10(13) . . ? C6 C7 C8 121.96(12) . . ? C6 C7 C15 121.21(11) . . ? C8 C7 C15 60.49(9) . . ? C9 C8 C7 122.15(12) . . ? C9 C8 C15 119.51(12) . . ? C7 C8 C15 60.11(9) . . ? C10 C9 C14 117.93(14) . . ? C10 C9 C8 119.36(13) . . ? C14 C9 C8 122.70(14) . . ? C9 C10 C11 121.18(15) . . ? C12 C11 C10 120.30(16) . . ? C13 C12 C11 119.22(15) . . ? C12 C13 C14 120.50(16) . . ? C9 C14 C13 120.86(15) . . ? C16 C15 C7 122.89(11) . . ? C16 C15 C8 123.49(12) . . ? C7 C15 C8 59.39(9) . . ? C15 C16 C24 120.89(12) . . ? C15 C16 C26 121.63(11) . . ? C24 C16 C26 106.40(11) . . ? C15 C16 C17 119.29(11) . . ? C24 C16 C17 59.26(9) . . ? C26 C16 C17 113.25(11) . . ? C18 C17 C24 121.94(12) . . ? C18 C17 C16 120.57(11) . . ? C24 C17 C16 59.60(9) . . ? C23 C18 C19 118.19(13) . . ? C23 C18 C17 123.08(13) . . ? C19 C18 C17 118.73(13) . . ? C20 C19 C18 121.04(15) . . ? C21 C20 C19 120.01(15) . . ? C20 C21 C22 119.71(14) . . ? C21 C22 C23 120.23(16) . . ? C18 C23 C22 120.79(15) . . ? C17 C24 C25 117.17(12) . . ? C17 C24 C16 61.13(9) . . ? C25 C24 C16 108.16(11) . . ? N1 C25 C24 101.63(11) . . ? N1 C26 C16 102.56(11) . . ? C28 C27 C33 120.82(13) . . ? C28 C27 S1 119.96(11) . . ? C33 C27 S1 119.21(11) . . ? C27 C28 C29 119.30(14) . . ? C30 C29 C28 120.91(14) . . ? C32 C30 C29 118.73(13) . . ? C32 C30 C31 120.26(15) . . ? C29 C30 C31 121.01(15) . . ? C33 C32 C30 121.39(14) . . ? C32 C33 C27 118.84(14) . . ? C25 N1 C26 109.67(10) . . ? C25 N1 S1 119.12(9) . . ? C26 N1 S1 121.63(9) . . ? O1 S1 O2 120.30(7) . . ? O1 S1 N1 106.38(6) . . ? O2 S1 N1 106.33(6) . . ? O1 S1 C27 107.79(6) . . ? O2 S1 C27 107.80(7) . . ? N1 S1 C27 107.66(6) . . ? 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 C6 C1 C2 C3 0.2(2) . . . . ? C1 C2 C3 C4 -0.9(2) . . . . ? C2 C3 C4 C5 0.6(2) . . . . ? C3 C4 C5 C6 0.6(2) . . . . ? C2 C1 C6 C5 0.9(2) . . . . ? C2 C1 C6 C7 179.27(13) . . . . ? C4 C5 C6 C1 -1.3(2) . . . . ? C4 C5 C6 C7 -179.69(13) . . . . ? C1 C6 C7 C8 34.75(19) . . . . ? C5 C6 C7 C8 -146.90(13) . . . . ? C1 C6 C7 C15 107.25(16) . . . . ? C5 C6 C7 C15 -74.41(18) . . . . ? C6 C7 C8 C9 -141.54(13) . . . . ? C15 C7 C8 C9 108.05(14) . . . . ? C6 C7 C8 C15 110.41(14) . . . . ? C7 C8 C9 C10 173.27(13) . . . . ? C15 C8 C9 C10 -115.42(15) . . . . ? C7 C8 C9 C14 -8.1(2) . . . . ? C15 C8 C9 C14 63.24(19) . . . . ? C14 C9 C10 C11 -0.7(2) . . . . ? C8 C9 C10 C11 178.06(14) . . . . ? C9 C10 C11 C12 0.8(2) . . . . ? C10 C11 C12 C13 -0.3(3) . . . . ? C11 C12 C13 C14 -0.3(3) . . . . ? C10 C9 C14 C13 0.1(2) . . . . ? C8 C9 C14 C13 -178.58(14) . . . . ? C12 C13 C14 C9 0.4(3) . . . . ? C6 C7 C15 C16 0.8(2) . . . . ? C8 C7 C15 C16 112.39(14) . . . . ? C6 C7 C15 C8 -111.61(15) . . . . ? C9 C8 C15 C16 136.25(13) . . . . ? C7 C8 C15 C16 -111.42(14) . . . . ? C9 C8 C15 C7 -112.33(14) . . . . ? C7 C15 C16 C24 79.39(17) . . . . ? C8 C15 C16 C24 151.98(13) . . . . ? C7 C15 C16 C26 -59.63(18) . . . . ? C8 C15 C16 C26 12.96(19) . . . . ? C7 C15 C16 C17 149.07(13) . . . . ? C8 C15 C16 C17 -138.34(13) . . . . ? C15 C16 C17 C18 0.89(19) . . . . ? C24 C16 C17 C18 111.47(15) . . . . ? C26 C16 C17 C18 -152.68(13) . . . . ? C15 C16 C17 C24 -110.57(14) . . . . ? C26 C16 C17 C24 95.85(12) . . . . ? C24 C17 C18 C23 -17.8(2) . . . . ? C16 C17 C18 C23 -88.91(17) . . . . ? C24 C17 C18 C19 162.65(13) . . . . ? C16 C17 C18 C19 91.57(16) . . . . ? C23 C18 C19 C20 1.7(2) . . . . ? C17 C18 C19 C20 -178.71(13) . . . . ? C18 C19 C20 C21 -0.1(2) . . . . ? C19 C20 C21 C22 -1.4(2) . . . . ? C20 C21 C22 C23 1.1(2) . . . . ? C19 C18 C23 C22 -2.0(2) . . . . ? C17 C18 C23 C22 178.46(13) . . . . ? C21 C22 C23 C18 0.6(2) . . . . ? C18 C17 C24 C25 154.07(12) . . . . ? C16 C17 C24 C25 -96.72(13) . . . . ? C18 C17 C24 C16 -109.21(14) . . . . ? C15 C16 C24 C17 107.90(13) . . . . ? C26 C16 C24 C17 -107.68(11) . . . . ? C15 C16 C24 C25 -140.51(12) . . . . ? C26 C16 C24 C25 3.90(14) . . . . ? C17 C16 C24 C25 111.58(12) . . . . ? C17 C24 C25 N1 43.69(15) . . . . ? C16 C24 C25 N1 -22.56(13) . . . . ? C15 C16 C26 N1 160.52(11) . . . . ? C24 C16 C26 N1 16.43(13) . . . . ? C17 C16 C26 N1 -46.61(14) . . . . ? C33 C27 C28 C29 0.4(2) . . . . ? S1 C27 C28 C29 179.43(10) . . . . ? C27 C28 C29 C30 -0.2(2) . . . . ? C28 C29 C30 C32 -0.4(2) . . . . ? C28 C29 C30 C31 179.68(14) . . . . ? C29 C30 C32 C33 0.8(2) . . . . ? C31 C30 C32 C33 -179.28(14) . . . . ? C30 C32 C33 C27 -0.6(2) . . . . ? C28 C27 C33 C32 0.0(2) . . . . ? S1 C27 C33 C32 -179.05(11) . . . . ? C24 C25 N1 C26 34.61(13) . . . . ? C24 C25 N1 S1 -178.61(9) . . . . ? C16 C26 N1 C25 -32.44(13) . . . . ? C16 C26 N1 S1 -178.24(9) . . . . ? C25 N1 S1 O1 49.68(11) . . . . ? C26 N1 S1 O1 -167.61(10) . . . . ? C25 N1 S1 O2 179.03(10) . . . . ? C26 N1 S1 O2 -38.26(12) . . . . ? C25 N1 S1 C27 -65.65(11) . . . . ? C26 N1 S1 C27 77.06(12) . . . . ? C28 C27 S1 O1 150.36(11) . . . . ? C33 C27 S1 O1 -30.60(13) . . . . ? C28 C27 S1 O2 19.10(13) . . . . ? C33 C27 S1 O2 -161.87(11) . . . . ? C28 C27 S1 N1 -95.25(12) . . . . ? C33 C27 S1 N1 83.79(12) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.457 _refine_diff_density_min -0.440 _refine_diff_density_rms 0.121 # Attachment 'web_deposit_cif_file_4_AntonioM.Echavarren_1276529606.cif' data_nm086pccn _database_code_depnum_ccdc_archive 'CCDC 780819' #TrackingRef 'web_deposit_cif_file_4_AntonioM.Echavarren_1276529606.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H29 N O2 S' _chemical_formula_weight 443.58 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 Orthorhombic _symmetry_space_group_name_H-M Pccn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-x, y+1/2, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'x, -y-1/2, z-1/2' '-x-1/2, y, z-1/2' _cell_length_a 34.3459(17) _cell_length_b 11.0908(6) _cell_length_c 12.4392(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4738.4(4) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9979 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 35.84 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.244 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1888 _exptl_absorpt_coefficient_mu 0.162 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.99 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details ; SADABS Version 2008/1 Bruker-Nonius Blessing, Acta Cryst. (1995) A51 33-38 ; _exptl_special_details ; It should be noted that the esd's of the cell dimensions are probably too low; they should be multiplied by a factor of 2 to 10 ; _diffrn_ambient_temperature 100(2) _diffrn_measurement_specimen_suppport 'magnetic support whith 10 micron nylon fiber cryoloop' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'rotating anode X-ray tube' _diffrn_source_type 'Bruker-Nonius FR 591' _diffrn_source_power 50 _diffrn_source_current 70 _diffrn_source_size '3 mm x 0.3 mm fine focus' _diffrn_radiation_monochromator 'Multilayer Montel 200 mirrors' _diffrn_detector_type '4K CCD area detector APEX II' _diffrn_measurement_device_type 'Kappa 4-axis goniometer bruker-nonius' _diffrn_measurement_method ; Fullsphere data collection, phi and omega scans ; _diffrn_detector_area_resol_mean 512 _diffrn_reflns_number 43672 _diffrn_reflns_av_R_equivalents 0.0434 _diffrn_reflns_av_sigmaI/netI 0.0435 _diffrn_reflns_limit_h_min -56 _diffrn_reflns_limit_h_max 50 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.19 _diffrn_reflns_theta_max 36.38 _reflns_number_total 10549 _reflns_number_gt 8021 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 v2009.1-0' _computing_cell_refinement 'Bruker APEX2 v2009.1-0' _computing_data_reduction 'Bruker SAINT V7.60A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXS-97 (Sheldrick, 2008)' _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^)+(0.0710P)^2^+1.2450P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10549 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0676 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1386 _refine_ls_wR_factor_gt 0.1260 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.002 _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 C1 C 0.28107(4) 0.99712(17) 0.66928(12) 0.0407(4) Uani 1 1 d . . . H1A H 0.2777 0.9899 0.7473 0.061 Uiso 1 1 calc R . . H1B H 0.3044 1.0450 0.6539 0.061 Uiso 1 1 calc R . . H1C H 0.2839 0.9166 0.6377 0.061 Uiso 1 1 calc R . . C2 C 0.24600(3) 1.05823(13) 0.62171(9) 0.0239(2) Uani 1 1 d . . . C3 C 0.24530(3) 1.08736(12) 0.51220(9) 0.0227(2) Uani 1 1 d . . . H3 H 0.2671 1.0684 0.4685 0.027 Uiso 1 1 calc R . . C4 C 0.21320(3) 1.14342(11) 0.46666(8) 0.0191(2) Uani 1 1 d . . . H4 H 0.2130 1.1630 0.3923 0.023 Uiso 1 1 calc R . . C5 C 0.18113(3) 1.17084(10) 0.53120(7) 0.01536(17) Uani 1 1 d . . . C6 C 0.18108(3) 1.14196(12) 0.64002(8) 0.0199(2) Uani 1 1 d . . . H6 H 0.1591 1.1601 0.6835 0.024 Uiso 1 1 calc R . . C7 C 0.21363(3) 1.08620(13) 0.68426(9) 0.0247(2) Uani 1 1 d . . . H7 H 0.2138 1.0668 0.7587 0.030 Uiso 1 1 calc R . . C8 C 0.09711(3) 1.04086(11) 0.48277(7) 0.0194(2) Uani 1 1 d . . . H8A H 0.0810 1.0716 0.5429 0.023 Uiso 1 1 calc R . . H8B H 0.1179 0.9881 0.5118 0.023 Uiso 1 1 calc R . . C9 C 0.07247(3) 0.97513(11) 0.40060(7) 0.01683(18) Uani 1 1 d . . . H9 H 0.0648 0.8894 0.4139 0.020 Uiso 1 1 calc R . . C10 C 0.08659(3) 1.01203(10) 0.29048(7) 0.01361(17) Uani 1 1 d . . . C11 C 0.11994(3) 1.09981(10) 0.30712(7) 0.01536(18) Uani 1 1 d . . . H11A H 0.1455 1.0592 0.2993 0.018 Uiso 1 1 calc R . . H11B H 0.1185 1.1679 0.2558 0.018 Uiso 1 1 calc R . . C12 C 0.04702(3) 1.05383(11) 0.33133(7) 0.01615(18) Uani 1 1 d . . . H12 H 0.0455 1.1404 0.3534 0.019 Uiso 1 1 calc R . . C13 C 0.01123(3) 1.00451(11) 0.27875(8) 0.0194(2) Uani 1 1 d . . . C14 C -0.01105(3) 0.91304(12) 0.32492(10) 0.0243(2) Uani 1 1 d . . . H14 H -0.0035 0.8796 0.3921 0.029 Uiso 1 1 calc R . . C15 C -0.04443(3) 0.87005(14) 0.27329(11) 0.0308(3) Uani 1 1 d . . . H15 H -0.0593 0.8075 0.3054 0.037 Uiso 1 1 calc R . . C16 C -0.05589(4) 0.91804(16) 0.17586(13) 0.0388(4) Uani 1 1 d . . . H16 H -0.0787 0.8892 0.1413 0.047 Uiso 1 1 calc R . . C17 C -0.03388(4) 1.00839(16) 0.12897(13) 0.0404(4) Uani 1 1 d . . . H17 H -0.0416 1.0413 0.0618 0.048 Uiso 1 1 calc R . . C18 C -0.00044(4) 1.05145(14) 0.17974(10) 0.0293(3) Uani 1 1 d . . . H18 H 0.0145 1.1132 0.1467 0.035 Uiso 1 1 calc R . . C19 C 0.08833(3) 0.93101(11) 0.19479(8) 0.01695(18) Uani 1 1 d . . . H19 H 0.0819 0.9719 0.1254 0.020 Uiso 1 1 calc R . . C20 C 0.07661(4) 0.80094(12) 0.19890(9) 0.0254(2) Uani 1 1 d . . . H20 H 0.0697 0.7710 0.2723 0.030 Uiso 1 1 calc R . . C21 C 0.11927(3) 0.83521(11) 0.18505(8) 0.0198(2) Uani 1 1 d . . . H21 H 0.1352 0.8245 0.2516 0.024 Uiso 1 1 calc R . . C22 C 0.05309(4) 0.74610(15) 0.10939(11) 0.0334(3) Uani 1 1 d . . . H22A H 0.0258 0.7704 0.1168 0.050 Uiso 1 1 calc R . . H22B H 0.0550 0.6580 0.1130 0.050 Uiso 1 1 calc R . . H22C H 0.0632 0.7742 0.0401 0.050 Uiso 1 1 calc R . . C23 C 0.14141(3) 0.81467(11) 0.08320(8) 0.01870(19) Uani 1 1 d . . . C24 C 0.13905(3) 0.89101(13) -0.00535(9) 0.0235(2) Uani 1 1 d . . . H24 H 0.1215 0.9572 -0.0038 0.028 Uiso 1 1 calc R . . C25 C 0.16194(4) 0.87219(14) -0.09603(10) 0.0282(3) Uani 1 1 d . . . H25 H 0.1596 0.9246 -0.1561 0.034 Uiso 1 1 calc R . . C26 C 0.18808(4) 0.77745(14) -0.09913(11) 0.0303(3) Uani 1 1 d . . . H26 H 0.2040 0.7655 -0.1607 0.036 Uiso 1 1 calc R . . C27 C 0.19098(4) 0.70025(15) -0.01228(12) 0.0334(3) Uani 1 1 d . . . H27 H 0.2089 0.6349 -0.0142 0.040 Uiso 1 1 calc R . . C28 C 0.16764(4) 0.71815(13) 0.07823(10) 0.0263(2) Uani 1 1 d . . . H28 H 0.1696 0.6641 0.1372 0.032 Uiso 1 1 calc R . . N1 N 0.11361(2) 1.14074(9) 0.41850(6) 0.01497(16) Uani 1 1 d . . . O1 O 0.15372(2) 1.32027(8) 0.38946(6) 0.01983(15) Uani 1 1 d . . . O2 O 0.11819(2) 1.29240(8) 0.56176(6) 0.02050(16) Uani 1 1 d . . . S1 S 0.140323(6) 1.24276(2) 0.474369(18) 0.01436(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 C1 0.0288(6) 0.0543(11) 0.0391(7) -0.0111(7) -0.0128(5) 0.0203(6) C2 0.0180(4) 0.0273(7) 0.0264(5) -0.0074(4) -0.0074(3) 0.0055(4) C3 0.0145(4) 0.0272(7) 0.0263(5) -0.0064(4) 0.0008(3) 0.0016(4) C4 0.0162(4) 0.0226(6) 0.0186(4) -0.0030(4) 0.0018(3) -0.0006(3) C5 0.0136(3) 0.0177(5) 0.0147(3) -0.0025(3) -0.0013(3) -0.0004(3) C6 0.0170(4) 0.0275(7) 0.0152(4) -0.0013(4) -0.0015(3) 0.0040(3) C7 0.0232(5) 0.0320(8) 0.0187(4) -0.0019(4) -0.0053(3) 0.0079(4) C8 0.0215(4) 0.0246(6) 0.0121(3) 0.0029(3) -0.0006(3) -0.0058(4) C9 0.0187(4) 0.0186(6) 0.0132(3) 0.0021(3) 0.0007(3) -0.0038(3) C10 0.0136(3) 0.0150(5) 0.0122(3) -0.0010(3) 0.0008(3) -0.0015(3) C11 0.0151(3) 0.0196(6) 0.0114(3) -0.0024(3) 0.0013(3) -0.0038(3) C12 0.0137(3) 0.0181(5) 0.0166(4) -0.0030(3) 0.0005(3) -0.0012(3) C13 0.0147(4) 0.0210(6) 0.0226(4) -0.0059(4) -0.0003(3) -0.0015(3) C14 0.0183(4) 0.0265(7) 0.0280(5) -0.0084(4) 0.0053(4) -0.0060(4) C15 0.0179(4) 0.0311(8) 0.0433(7) -0.0153(6) 0.0062(4) -0.0082(4) C16 0.0215(5) 0.0421(10) 0.0527(8) -0.0163(7) -0.0116(5) -0.0053(5) C17 0.0326(6) 0.0424(10) 0.0463(8) -0.0021(7) -0.0223(6) -0.0052(6) C18 0.0244(5) 0.0312(8) 0.0323(6) 0.0002(5) -0.0109(4) -0.0043(5) C19 0.0176(4) 0.0177(6) 0.0155(4) -0.0035(3) 0.0009(3) -0.0010(3) C20 0.0309(5) 0.0211(7) 0.0242(5) -0.0061(4) 0.0094(4) -0.0079(4) C21 0.0243(4) 0.0172(6) 0.0179(4) -0.0001(4) 0.0016(3) 0.0015(4) C22 0.0329(6) 0.0326(8) 0.0346(6) -0.0171(5) 0.0110(5) -0.0153(5) C23 0.0188(4) 0.0171(6) 0.0203(4) -0.0042(4) 0.0012(3) -0.0001(3) C24 0.0249(5) 0.0235(7) 0.0221(4) 0.0010(4) 0.0049(4) 0.0050(4) C25 0.0304(5) 0.0318(8) 0.0223(5) -0.0024(5) 0.0074(4) 0.0011(5) C26 0.0255(5) 0.0361(8) 0.0294(5) -0.0115(5) 0.0072(4) 0.0004(5) C27 0.0300(6) 0.0309(8) 0.0392(7) -0.0105(6) 0.0021(5) 0.0121(5) C28 0.0306(5) 0.0195(7) 0.0288(5) -0.0028(4) -0.0010(4) 0.0068(4) N1 0.0160(3) 0.0188(5) 0.0101(3) -0.0010(3) 0.0000(2) -0.0040(3) O1 0.0244(3) 0.0173(4) 0.0178(3) 0.0022(3) -0.0020(3) -0.0039(3) O2 0.0212(3) 0.0246(5) 0.0157(3) -0.0064(3) -0.0010(2) 0.0056(3) S1 0.01529(10) 0.01587(14) 0.01192(9) -0.00180(8) -0.00156(7) 0.00024(7) _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 C1 C2 1.5035(17) . ? C2 C7 1.3920(16) . ? C2 C3 1.4002(17) . ? C3 C4 1.3869(15) . ? C4 C5 1.3965(13) . ? C5 C6 1.3911(14) . ? C5 S1 1.7608(10) . ? C6 C7 1.3909(15) . ? C8 N1 1.4790(14) . ? C8 C9 1.5141(14) . ? C9 C12 1.5061(15) . ? C9 C10 1.5096(13) . ? C10 C19 1.4926(14) . ? C10 C11 1.5174(14) . ? C10 C12 1.5231(13) . ? C11 N1 1.4740(12) . ? C12 C13 1.4961(14) . ? C13 C14 1.3943(17) . ? C13 C18 1.3958(17) . ? C14 C15 1.3981(16) . ? C15 C16 1.381(2) . ? C16 C17 1.384(2) . ? C17 C18 1.3949(17) . ? C19 C20 1.4986(18) . ? C19 C21 1.5076(16) . ? C20 C22 1.5041(17) . ? C20 C21 1.5236(16) . ? C21 C23 1.4951(14) . ? C23 C24 1.3916(17) . ? C23 C28 1.4005(17) . ? C24 C25 1.3908(15) . ? C25 C26 1.383(2) . ? C26 C27 1.382(2) . ? C27 C28 1.3963(18) . ? N1 S1 1.6140(9) . ? O1 S1 1.4374(8) . ? O2 S1 1.4363(8) . ? 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 C7 C2 C3 118.61(10) . . ? C7 C2 C1 121.35(11) . . ? C3 C2 C1 120.04(11) . . ? C4 C3 C2 120.96(10) . . ? C3 C4 C5 119.33(10) . . ? C6 C5 C4 120.68(9) . . ? C6 C5 S1 119.61(7) . . ? C4 C5 S1 119.71(8) . . ? C7 C6 C5 119.11(9) . . ? C6 C7 C2 121.31(10) . . ? N1 C8 C9 102.11(7) . . ? C12 C9 C10 60.67(6) . . ? C12 C9 C8 115.57(10) . . ? C10 C9 C8 107.61(8) . . ? C19 C10 C9 124.98(10) . . ? C19 C10 C11 117.69(8) . . ? C9 C10 C11 107.02(7) . . ? C19 C10 C12 119.02(8) . . ? C9 C10 C12 59.55(6) . . ? C11 C10 C12 115.64(9) . . ? N1 C11 C10 102.39(7) . . ? C13 C12 C9 121.00(10) . . ? C13 C12 C10 118.42(9) . . ? C9 C12 C10 59.78(6) . . ? C14 C13 C18 118.50(10) . . ? C14 C13 C12 122.46(10) . . ? C18 C13 C12 119.03(10) . . ? C13 C14 C15 120.59(12) . . ? C16 C15 C14 120.36(13) . . ? C15 C16 C17 119.55(11) . . ? C16 C17 C18 120.45(14) . . ? C17 C18 C13 120.54(13) . . ? C10 C19 C20 122.79(9) . . ? C10 C19 C21 121.11(9) . . ? C20 C19 C21 60.90(8) . . ? C19 C20 C22 120.55(12) . . ? C19 C20 C21 59.84(7) . . ? C22 C20 C21 122.25(9) . . ? C23 C21 C19 122.28(10) . . ? C23 C21 C20 123.16(9) . . ? C19 C21 C20 59.25(8) . . ? C24 C23 C28 117.88(10) . . ? C24 C23 C21 123.25(10) . . ? C28 C23 C21 118.75(11) . . ? C25 C24 C23 121.18(12) . . ? C26 C25 C24 120.25(13) . . ? C27 C26 C25 119.72(11) . . ? C26 C27 C28 120.06(13) . . ? C27 C28 C23 120.90(13) . . ? C11 N1 C8 109.50(8) . . ? C11 N1 S1 122.47(7) . . ? C8 N1 S1 120.67(6) . . ? O2 S1 O1 119.76(5) . . ? O2 S1 N1 107.08(5) . . ? O1 S1 N1 106.54(4) . . ? O2 S1 C5 106.93(4) . . ? O1 S1 C5 108.13(5) . . ? N1 S1 C5 107.92(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 C7 C2 C3 C4 0.3(2) . . . . ? C1 C2 C3 C4 179.81(13) . . . . ? C2 C3 C4 C5 -0.13(18) . . . . ? C3 C4 C5 C6 -0.32(17) . . . . ? C3 C4 C5 S1 179.65(9) . . . . ? C4 C5 C6 C7 0.58(18) . . . . ? S1 C5 C6 C7 -179.39(10) . . . . ? C5 C6 C7 C2 -0.4(2) . . . . ? C3 C2 C7 C6 0.0(2) . . . . ? C1 C2 C7 C6 -179.54(14) . . . . ? N1 C8 C9 C12 -46.10(11) . . . . ? N1 C8 C9 C10 19.20(11) . . . . ? C12 C9 C10 C19 -105.99(10) . . . . ? C8 C9 C10 C19 144.07(10) . . . . ? C12 C9 C10 C11 110.18(9) . . . . ? C8 C9 C10 C11 0.24(12) . . . . ? C8 C9 C10 C12 -109.94(10) . . . . ? C19 C10 C11 N1 -166.57(9) . . . . ? C9 C10 C11 N1 -19.67(11) . . . . ? C12 C10 C11 N1 44.17(11) . . . . ? C10 C9 C12 C13 107.01(10) . . . . ? C8 C9 C12 C13 -156.34(9) . . . . ? C8 C9 C12 C10 96.65(9) . . . . ? C19 C10 C12 C13 4.49(15) . . . . ? C9 C10 C12 C13 -111.26(11) . . . . ? C11 C10 C12 C13 153.33(9) . . . . ? C19 C10 C12 C9 115.75(11) . . . . ? C11 C10 C12 C9 -95.42(9) . . . . ? C9 C12 C13 C14 31.70(15) . . . . ? C10 C12 C13 C14 101.67(12) . . . . ? C9 C12 C13 C18 -148.29(11) . . . . ? C10 C12 C13 C18 -78.32(15) . . . . ? C18 C13 C14 C15 -0.38(18) . . . . ? C12 C13 C14 C15 179.63(11) . . . . ? C13 C14 C15 C16 -0.2(2) . . . . ? C14 C15 C16 C17 0.6(2) . . . . ? C15 C16 C17 C18 -0.4(2) . . . . ? C16 C17 C18 C13 -0.3(2) . . . . ? C14 C13 C18 C17 0.6(2) . . . . ? C12 C13 C18 C17 -179.36(13) . . . . ? C9 C10 C19 C20 -1.13(15) . . . . ? C11 C10 C19 C20 139.27(11) . . . . ? C12 C10 C19 C20 -72.52(14) . . . . ? C9 C10 C19 C21 -74.46(13) . . . . ? C11 C10 C19 C21 65.94(13) . . . . ? C12 C10 C19 C21 -145.85(10) . . . . ? C10 C19 C20 C22 137.88(11) . . . . ? C21 C19 C20 C22 -111.94(12) . . . . ? C10 C19 C20 C21 -110.17(11) . . . . ? C10 C19 C21 C23 -135.02(11) . . . . ? C20 C19 C21 C23 112.15(12) . . . . ? C10 C19 C21 C20 112.83(11) . . . . ? C19 C20 C21 C23 -110.70(12) . . . . ? C22 C20 C21 C23 -1.5(2) . . . . ? C22 C20 C21 C19 109.18(15) . . . . ? C19 C21 C23 C24 8.60(17) . . . . ? C20 C21 C23 C24 80.57(16) . . . . ? C19 C21 C23 C28 -175.35(11) . . . . ? C20 C21 C23 C28 -103.39(14) . . . . ? C28 C23 C24 C25 0.06(18) . . . . ? C21 C23 C24 C25 176.14(11) . . . . ? C23 C24 C25 C26 -0.9(2) . . . . ? C24 C25 C26 C27 1.0(2) . . . . ? C25 C26 C27 C28 -0.1(2) . . . . ? C26 C27 C28 C23 -0.8(2) . . . . ? C24 C23 C28 C27 0.78(19) . . . . ? C21 C23 C28 C27 -175.48(12) . . . . ? C10 C11 N1 C8 33.51(10) . . . . ? C10 C11 N1 S1 -176.40(7) . . . . ? C9 C8 N1 C11 -33.28(10) . . . . ? C9 C8 N1 S1 176.00(7) . . . . ? C11 N1 S1 O2 158.39(8) . . . . ? C8 N1 S1 O2 -54.74(9) . . . . ? C11 N1 S1 O1 29.12(10) . . . . ? C8 N1 S1 O1 176.00(8) . . . . ? C11 N1 S1 C5 -86.81(9) . . . . ? C8 N1 S1 C5 60.06(9) . . . . ? C6 C5 S1 O2 17.62(11) . . . . ? C4 C5 S1 O2 -162.35(9) . . . . ? C6 C5 S1 O1 147.82(9) . . . . ? C4 C5 S1 O1 -32.14(11) . . . . ? C6 C5 S1 N1 -97.29(10) . . . . ? C4 C5 S1 N1 82.74(10) . . . . ? _diffrn_measured_fraction_theta_max 0.913 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 0.695 _refine_diff_density_min -0.344 _refine_diff_density_rms 0.068 # Attachment 'web_deposit_cif_file_5_AntonioM.Echavarren_1276529606.cif' data_ehg163-05t _database_code_depnum_ccdc_archive 'CCDC 780820' #TrackingRef 'web_deposit_cif_file_5_AntonioM.Echavarren_1276529606.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H32 O4 S2' _chemical_formula_weight 544.70 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' 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 10.0661(9) _cell_length_b 11.2303(12) _cell_length_c 12.7093(12) _cell_angle_alpha 108.467(5) _cell_angle_beta 92.142(5) _cell_angle_gamma 102.893(5) _cell_volume 1319.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5163 _cell_measurement_theta_min 2.85 _cell_measurement_theta_max 36.26 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.240 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.94 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details ; TWINABS Version 2008/4 Bruker AXS Blessing, Acta Cryst. (1995) A51 33-38 ; _exptl_special_details ; It should be noted that the esd's of the cell dimensions are probably too low; they should be multiplied by a factor of 2 to 10 ; _diffrn_ambient_temperature 100(2) _diffrn_measurement_specimen_suppport 'magnetic support whith 10 micron nylon fiber cryoloop' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'rotating anode X-ray tube' _diffrn_source_type 'Bruker-Nonius FR 591' _diffrn_source_power 50 _diffrn_source_current 70 _diffrn_source_size '3 mm x 0.3 mm fine focus' _diffrn_radiation_monochromator 'Multilayer Montel 200 mirrors' _diffrn_detector_type '4K CCD area detector APEX II' _diffrn_measurement_device_type 'Kappa 4-axis goniometer bruker-nonius' _diffrn_measurement_method ; Fullsphere data collection, phi and omega scans ; _diffrn_detector_area_resol_mean 512 _diffrn_reflns_number 19756 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0424 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.78 _diffrn_reflns_theta_max 36.35 _reflns_number_total 19756 _reflns_number_gt 16892 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 v2009.1-0' _computing_cell_refinement 'Bruker APEX2 v2009.1-0' _computing_data_reduction 'Bruker SAINT V7.60A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXS-97 (Sheldrick, 2008)' _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^)+(0.0652P)^2^+0.1594P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 19756 _refine_ls_number_parameters 344 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0495 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.1158 _refine_ls_wR_factor_gt 0.1105 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 S1 S 0.879234(19) 0.72553(2) 0.250282(16) 0.01283(4) Uani 1 1 d . . . O1 O 0.80343(6) 0.74619(7) 0.16220(5) 0.01855(12) Uani 1 1 d . . . C1 C 0.76376(8) 0.70633(8) 0.35586(6) 0.01236(12) Uani 1 1 d . . . S2 S 0.591067(19) 0.60733(2) 0.293183(17) 0.01354(4) Uani 1 1 d . . . O2 O 0.99724(6) 0.82606(7) 0.31350(6) 0.01834(12) Uani 1 1 d . . . C2 C 0.76130(8) 0.84570(8) 0.43170(7) 0.01384(13) Uani 1 1 d . . . H2A H 0.8121 0.9113 0.4013 0.017 Uiso 1 1 calc R . . H2B H 0.6657 0.8541 0.4363 0.017 Uiso 1 1 calc R . . O3 O 0.60578(6) 0.49785(7) 0.20146(5) 0.01748(12) Uani 1 1 d . . . C3 C 0.82980(8) 0.86402(8) 0.54621(6) 0.01249(13) Uani 1 1 d . . . H3 H 0.8924 0.9498 0.5902 0.015 Uiso 1 1 calc R . . O4 O 0.52249(7) 0.58515(8) 0.38536(6) 0.02045(13) Uani 1 1 d . . . C4 C 0.86832(8) 0.74189(8) 0.54594(6) 0.01187(12) Uani 1 1 d . . . C5 C 0.82312(8) 0.63997(9) 0.43047(6) 0.01369(13) Uani 1 1 d . . . H5A H 0.7523 0.5654 0.4350 0.016 Uiso 1 1 calc R . . H5B H 0.9022 0.6083 0.3990 0.016 Uiso 1 1 calc R . . C6 C 0.74928(8) 0.78175(8) 0.60755(6) 0.01267(13) Uani 1 1 d . . . H6 H 0.6569 0.7297 0.5673 0.015 Uiso 1 1 calc R . . C7 C 0.75453(8) 0.82075(8) 0.73133(6) 0.01307(13) Uani 1 1 d . . . C8 C 0.66687(9) 0.73729(10) 0.77437(7) 0.01731(15) Uani 1 1 d . . . H8 H 0.6068 0.6604 0.7247 0.021 Uiso 1 1 calc R . . C9 C 0.66644(10) 0.76527(11) 0.88904(8) 0.02207(17) Uani 1 1 d . . . H9 H 0.6070 0.7069 0.9170 0.026 Uiso 1 1 calc R . . C10 C 0.75216(10) 0.87786(11) 0.96287(7) 0.02098(17) Uani 1 1 d . . . H10 H 0.7520 0.8968 1.0412 0.025 Uiso 1 1 calc R . . C11 C 0.83824(9) 0.96248(10) 0.92083(7) 0.01765(16) Uani 1 1 d . . . H11 H 0.8967 1.0401 0.9708 0.021 Uiso 1 1 calc R . . C12 C 0.83967(8) 0.93454(9) 0.80579(7) 0.01539(14) Uani 1 1 d . . . H12 H 0.8989 0.9933 0.7781 0.018 Uiso 1 1 calc R . . C13 C 0.99538(7) 0.73425(8) 0.60548(6) 0.01252(13) Uani 1 1 d . . . H13 H 0.9865 0.6565 0.6295 0.015 Uiso 1 1 calc R . . C14 C 1.09901(8) 0.85464(8) 0.67750(6) 0.01291(13) Uani 1 1 d . . . H14 H 1.0795 0.9411 0.6888 0.015 Uiso 1 1 calc R . . C15 C 1.20682(8) 0.84336(9) 0.75891(7) 0.01549(14) Uani 1 1 d . . . H15 H 1.1832 0.8587 0.8370 0.019 Uiso 1 1 calc R . . C16 C 1.34242(8) 0.93256(10) 0.74705(8) 0.01851(16) Uani 1 1 d . . . H16A H 1.4160 0.9434 0.8057 0.022 Uiso 1 1 calc R . . H16B H 1.3302 1.0189 0.7510 0.022 Uiso 1 1 calc R . . C17 C 1.37524(9) 0.85737(10) 0.62836(8) 0.02008(17) Uani 1 1 d . . . H17A H 1.3758 0.9086 0.5776 0.024 Uiso 1 1 calc R . . H17B H 1.4651 0.8360 0.6326 0.024 Uiso 1 1 calc R . . C18 C 1.25651(8) 0.73321(9) 0.58882(7) 0.01700(15) Uani 1 1 d . . . H18 H 1.2746 0.6588 0.5278 0.020 Uiso 1 1 calc R . . C19 C 1.13047(8) 0.77823(9) 0.56327(7) 0.01371(13) Uani 1 1 d . . . H19 H 1.1298 0.8161 0.5019 0.016 Uiso 1 1 calc R . . C20 C 1.23320(9) 0.70972(10) 0.70013(8) 0.01828(15) Uani 1 1 d . . . H20A H 1.3154 0.6965 0.7356 0.022 Uiso 1 1 calc R . . H20B H 1.1526 0.6374 0.6932 0.022 Uiso 1 1 calc R . . C21 C 0.93826(8) 0.58393(9) 0.19525(7) 0.01441(14) Uani 1 1 d . . . C22 C 1.06305(8) 0.57990(9) 0.24389(7) 0.01738(15) Uani 1 1 d . . . H22 H 1.1116 0.6498 0.3073 0.021 Uiso 1 1 calc R . . C23 C 1.11541(9) 0.47261(10) 0.19861(8) 0.02185(17) Uani 1 1 d . . . H23 H 1.1998 0.4684 0.2315 0.026 Uiso 1 1 calc R . . C24 C 1.04450(10) 0.37139(11) 0.10514(9) 0.02440(19) Uani 1 1 d . . . H24 H 1.0804 0.2980 0.0744 0.029 Uiso 1 1 calc R . . C25 C 0.92141(10) 0.37732(11) 0.05659(8) 0.02372(19) Uani 1 1 d . . . H25 H 0.8738 0.3080 -0.0076 0.028 Uiso 1 1 calc R . . C26 C 0.86702(9) 0.48373(10) 0.10096(7) 0.01848(16) Uani 1 1 d . . . H26 H 0.7829 0.4880 0.0676 0.022 Uiso 1 1 calc R . . C27 C 0.50219(8) 0.69897(9) 0.24089(7) 0.01519(14) Uani 1 1 d . . . C28 C 0.49823(8) 0.68630(10) 0.12823(7) 0.01802(16) Uani 1 1 d . . . H28 H 0.5467 0.6320 0.0801 0.022 Uiso 1 1 calc R . . C29 C 0.42212(9) 0.75461(11) 0.08756(8) 0.02297(18) Uani 1 1 d . . . H29 H 0.4174 0.7466 0.0107 0.028 Uiso 1 1 calc R . . C30 C 0.35270(9) 0.83482(11) 0.15907(9) 0.0259(2) Uani 1 1 d . . . H30 H 0.3034 0.8835 0.1311 0.031 Uiso 1 1 calc R . . C31 C 0.35454(9) 0.84447(11) 0.27018(9) 0.0252(2) Uani 1 1 d . . . H31 H 0.3052 0.8983 0.3178 0.030 Uiso 1 1 calc R . . C32 C 0.42848(8) 0.77557(10) 0.31242(8) 0.02016(17) Uani 1 1 d . . . H32 H 0.4290 0.7804 0.3884 0.024 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 0.01373(7) 0.01133(9) 0.01362(8) 0.00522(7) 0.00182(6) 0.00191(6) O1 0.0206(3) 0.0228(4) 0.0168(3) 0.0117(3) 0.0028(2) 0.0071(2) C1 0.0148(3) 0.0103(3) 0.0116(3) 0.0038(3) 0.0009(2) 0.0023(2) S2 0.01380(8) 0.01200(9) 0.01353(8) 0.00402(7) 0.00152(6) 0.00101(6) O2 0.0161(2) 0.0124(3) 0.0229(3) 0.0042(2) 0.0014(2) -0.0010(2) C2 0.0180(3) 0.0103(3) 0.0128(3) 0.0032(3) 0.0007(2) 0.0040(3) O3 0.0185(3) 0.0128(3) 0.0178(3) 0.0014(2) 0.0000(2) 0.0028(2) C3 0.0147(3) 0.0099(3) 0.0124(3) 0.0033(3) 0.0013(2) 0.0029(2) O4 0.0197(3) 0.0225(4) 0.0181(3) 0.0093(3) 0.0046(2) -0.0011(2) C4 0.0137(3) 0.0102(3) 0.0113(3) 0.0031(2) 0.0014(2) 0.0028(2) C5 0.0183(3) 0.0110(4) 0.0120(3) 0.0038(3) 0.0010(2) 0.0042(3) C6 0.0129(3) 0.0122(4) 0.0121(3) 0.0034(3) 0.0017(2) 0.0025(2) C7 0.0131(3) 0.0137(4) 0.0132(3) 0.0043(3) 0.0026(2) 0.0049(2) C8 0.0189(3) 0.0164(4) 0.0162(3) 0.0053(3) 0.0047(3) 0.0033(3) C9 0.0297(4) 0.0211(5) 0.0187(4) 0.0096(3) 0.0099(3) 0.0072(4) C10 0.0307(4) 0.0218(5) 0.0135(3) 0.0060(3) 0.0049(3) 0.0119(4) C11 0.0204(3) 0.0182(4) 0.0137(3) 0.0020(3) 0.0003(3) 0.0086(3) C12 0.0155(3) 0.0149(4) 0.0145(3) 0.0028(3) 0.0024(2) 0.0041(3) C13 0.0134(3) 0.0115(3) 0.0125(3) 0.0037(3) 0.0011(2) 0.0033(2) C14 0.0142(3) 0.0111(3) 0.0127(3) 0.0028(3) 0.0018(2) 0.0035(2) C15 0.0165(3) 0.0151(4) 0.0137(3) 0.0036(3) 0.0002(2) 0.0037(3) C16 0.0157(3) 0.0182(4) 0.0194(4) 0.0043(3) -0.0002(3) 0.0029(3) C17 0.0145(3) 0.0213(5) 0.0225(4) 0.0043(3) 0.0034(3) 0.0047(3) C18 0.0163(3) 0.0162(4) 0.0182(3) 0.0029(3) 0.0028(3) 0.0074(3) C19 0.0141(3) 0.0139(4) 0.0132(3) 0.0040(3) 0.0031(2) 0.0042(3) C20 0.0195(3) 0.0157(4) 0.0207(4) 0.0062(3) -0.0013(3) 0.0068(3) C21 0.0146(3) 0.0142(4) 0.0143(3) 0.0048(3) 0.0029(2) 0.0030(3) C22 0.0151(3) 0.0180(4) 0.0184(4) 0.0050(3) 0.0018(3) 0.0045(3) C23 0.0180(3) 0.0200(5) 0.0276(4) 0.0063(4) 0.0040(3) 0.0071(3) C24 0.0233(4) 0.0176(5) 0.0308(5) 0.0038(4) 0.0078(3) 0.0076(3) C25 0.0214(4) 0.0196(5) 0.0233(4) -0.0013(4) 0.0036(3) 0.0035(3) C26 0.0171(3) 0.0190(4) 0.0164(3) 0.0025(3) 0.0025(3) 0.0035(3) C27 0.0123(3) 0.0155(4) 0.0164(3) 0.0035(3) 0.0013(2) 0.0033(3) C28 0.0154(3) 0.0220(5) 0.0176(4) 0.0068(3) 0.0013(3) 0.0063(3) C29 0.0176(3) 0.0282(5) 0.0260(4) 0.0125(4) -0.0010(3) 0.0070(3) C30 0.0166(3) 0.0227(5) 0.0386(5) 0.0096(4) -0.0030(3) 0.0069(3) C31 0.0152(3) 0.0217(5) 0.0338(5) 0.0005(4) 0.0011(3) 0.0076(3) C32 0.0140(3) 0.0205(4) 0.0222(4) 0.0015(3) 0.0033(3) 0.0048(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.4383(6) . ? S1 O2 1.4445(7) . ? S1 C21 1.7661(9) . ? S1 C1 1.8402(8) . ? C1 C5 1.5542(11) . ? C1 C2 1.5629(12) . ? C1 S2 1.8345(8) . ? S2 O3 1.4418(7) . ? S2 O4 1.4421(7) . ? S2 C27 1.7610(9) . ? C2 C3 1.5191(11) . ? C3 C4 1.5052(12) . ? C3 C6 1.5125(12) . ? C4 C13 1.4945(10) . ? C4 C5 1.5245(11) . ? C4 C6 1.5286(10) . ? C6 C7 1.4888(11) . ? C7 C12 1.3955(12) . ? C7 C8 1.3957(13) . ? C8 C9 1.3905(12) . ? C9 C10 1.3873(15) . ? C10 C11 1.3886(15) . ? C11 C12 1.3962(12) . ? C13 C14 1.5064(12) . ? C13 C19 1.5177(11) . ? C14 C19 1.5201(11) . ? C14 C15 1.5248(11) . ? C15 C20 1.5373(13) . ? C15 C16 1.5461(13) . ? C16 C17 1.5660(13) . ? C17 C18 1.5469(14) . ? C18 C19 1.5265(11) . ? C18 C20 1.5360(13) . ? C21 C26 1.3920(12) . ? C21 C22 1.3954(11) . ? C22 C23 1.3884(13) . ? C23 C24 1.3899(15) . ? C24 C25 1.3878(14) . ? C25 C26 1.3907(14) . ? C27 C28 1.3914(12) . ? C27 C32 1.3987(12) . ? C28 C29 1.3881(13) . ? C29 C30 1.3912(14) . ? C30 C31 1.3807(16) . ? C31 C32 1.3898(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 O2 118.75(4) . . ? O1 S1 C21 109.51(4) . . ? O2 S1 C21 106.20(4) . . ? O1 S1 C1 108.21(4) . . ? O2 S1 C1 104.06(4) . . ? C21 S1 C1 109.82(4) . . ? C5 C1 C2 107.82(6) . . ? C5 C1 S2 108.00(6) . . ? C2 C1 S2 111.86(5) . . ? C5 C1 S1 109.76(5) . . ? C2 C1 S1 106.84(6) . . ? S2 C1 S1 112.47(4) . . ? O3 S2 O4 119.23(5) . . ? O3 S2 C27 108.76(4) . . ? O4 S2 C27 106.49(4) . . ? O3 S2 C1 107.74(4) . . ? O4 S2 C1 104.92(4) . . ? C27 S2 C1 109.41(4) . . ? C3 C2 C1 106.14(6) . . ? C4 C3 C6 60.87(5) . . ? C4 C3 C2 110.07(7) . . ? C6 C3 C2 114.81(7) . . ? C13 C4 C3 126.17(7) . . ? C13 C4 C5 114.88(6) . . ? C3 C4 C5 108.83(6) . . ? C13 C4 C6 122.24(6) . . ? C3 C4 C6 59.80(5) . . ? C5 C4 C6 113.71(6) . . ? C4 C5 C1 106.86(7) . . ? C7 C6 C3 124.25(7) . . ? C7 C6 C4 122.23(6) . . ? C3 C6 C4 59.33(5) . . ? C12 C7 C8 118.59(8) . . ? C12 C7 C6 124.43(8) . . ? C8 C7 C6 116.98(8) . . ? C9 C8 C7 120.80(9) . . ? C10 C9 C8 120.46(9) . . ? C9 C10 C11 119.16(8) . . ? C10 C11 C12 120.63(9) . . ? C7 C12 C11 120.34(8) . . ? C4 C13 C14 121.39(7) . . ? C4 C13 C19 117.01(7) . . ? C14 C13 C19 60.35(5) . . ? C13 C14 C19 60.19(5) . . ? C13 C14 C15 119.36(7) . . ? C19 C14 C15 104.07(6) . . ? C14 C15 C20 103.77(7) . . ? C14 C15 C16 105.08(7) . . ? C20 C15 C16 100.32(7) . . ? C15 C16 C17 102.71(7) . . ? C18 C17 C16 103.28(7) . . ? C19 C18 C20 103.13(6) . . ? C19 C18 C17 105.05(8) . . ? C20 C18 C17 100.57(7) . . ? C13 C19 C14 59.46(5) . . ? C13 C19 C18 120.82(8) . . ? C14 C19 C18 104.06(6) . . ? C18 C20 C15 94.78(7) . . ? C26 C21 C22 121.21(8) . . ? C26 C21 S1 120.59(6) . . ? C22 C21 S1 118.03(7) . . ? C23 C22 C21 119.25(8) . . ? C22 C23 C24 120.05(8) . . ? C25 C24 C23 120.17(9) . . ? C24 C25 C26 120.64(9) . . ? C25 C26 C21 118.68(8) . . ? C28 C27 C32 121.52(8) . . ? C28 C27 S2 119.57(6) . . ? C32 C27 S2 118.72(7) . . ? C29 C28 C27 118.68(8) . . ? C28 C29 C30 120.13(9) . . ? C31 C30 C29 120.79(9) . . ? C30 C31 C32 120.06(9) . . ? C31 C32 C27 118.74(9) . . ? 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 O1 S1 C1 C5 161.37(6) . . . . ? O2 S1 C1 C5 -71.45(6) . . . . ? C21 S1 C1 C5 41.88(7) . . . . ? O1 S1 C1 C2 -81.99(6) . . . . ? O2 S1 C1 C2 45.19(6) . . . . ? C21 S1 C1 C2 158.52(5) . . . . ? O1 S1 C1 S2 41.12(6) . . . . ? O2 S1 C1 S2 168.30(4) . . . . ? C21 S1 C1 S2 -78.37(5) . . . . ? C5 C1 S2 O3 -78.24(6) . . . . ? C2 C1 S2 O3 163.27(6) . . . . ? S1 C1 S2 O3 43.02(6) . . . . ? C5 C1 S2 O4 49.77(6) . . . . ? C2 C1 S2 O4 -68.72(7) . . . . ? S1 C1 S2 O4 171.03(5) . . . . ? C5 C1 S2 C27 163.68(5) . . . . ? C2 C1 S2 C27 45.19(7) . . . . ? S1 C1 S2 C27 -75.06(5) . . . . ? C5 C1 C2 C3 4.81(8) . . . . ? S2 C1 C2 C3 123.41(6) . . . . ? S1 C1 C2 C3 -113.11(6) . . . . ? C1 C2 C3 C4 -2.47(8) . . . . ? C1 C2 C3 C6 -68.76(8) . . . . ? C6 C3 C4 C13 -109.82(8) . . . . ? C2 C3 C4 C13 142.26(7) . . . . ? C6 C3 C4 C5 107.05(7) . . . . ? C2 C3 C4 C5 -0.87(9) . . . . ? C2 C3 C4 C6 -107.92(7) . . . . ? C13 C4 C5 C1 -143.86(7) . . . . ? C3 C4 C5 C1 3.87(8) . . . . ? C6 C4 C5 C1 68.36(9) . . . . ? C2 C1 C5 C4 -5.35(8) . . . . ? S2 C1 C5 C4 -126.40(6) . . . . ? S1 C1 C5 C4 110.67(6) . . . . ? C4 C3 C6 C7 110.26(8) . . . . ? C2 C3 C6 C7 -149.64(7) . . . . ? C2 C3 C6 C4 100.10(7) . . . . ? C13 C4 C6 C7 2.56(13) . . . . ? C3 C4 C6 C7 -113.56(9) . . . . ? C5 C4 C6 C7 147.68(8) . . . . ? C13 C4 C6 C3 116.12(9) . . . . ? C5 C4 C6 C3 -98.76(8) . . . . ? C3 C6 C7 C12 -3.59(12) . . . . ? C4 C6 C7 C12 68.94(11) . . . . ? C3 C6 C7 C8 175.85(7) . . . . ? C4 C6 C7 C8 -111.62(9) . . . . ? C12 C7 C8 C9 -1.44(12) . . . . ? C6 C7 C8 C9 179.09(8) . . . . ? C7 C8 C9 C10 0.84(14) . . . . ? C8 C9 C10 C11 0.15(14) . . . . ? C9 C10 C11 C12 -0.51(13) . . . . ? C8 C7 C12 C11 1.08(11) . . . . ? C6 C7 C12 C11 -179.49(7) . . . . ? C10 C11 C12 C7 -0.11(12) . . . . ? C3 C4 C13 C14 2.02(11) . . . . ? C5 C4 C13 C14 143.27(7) . . . . ? C6 C4 C13 C14 -71.98(11) . . . . ? C3 C4 C13 C19 -68.14(10) . . . . ? C5 C4 C13 C19 73.10(10) . . . . ? C6 C4 C13 C19 -142.14(8) . . . . ? C4 C13 C14 C19 -105.36(8) . . . . ? C4 C13 C14 C15 164.68(7) . . . . ? C19 C13 C14 C15 -89.95(7) . . . . ? C13 C14 C15 C20 32.03(9) . . . . ? C19 C14 C15 C20 -31.42(9) . . . . ? C13 C14 C15 C16 136.92(7) . . . . ? C19 C14 C15 C16 73.47(8) . . . . ? C14 C15 C16 C17 -70.42(8) . . . . ? C20 C15 C16 C17 37.02(8) . . . . ? C15 C16 C17 C18 -1.45(9) . . . . ? C16 C17 C18 C19 72.17(8) . . . . ? C16 C17 C18 C20 -34.65(8) . . . . ? C4 C13 C19 C14 112.49(8) . . . . ? C4 C13 C19 C18 -158.87(7) . . . . ? C14 C13 C19 C18 88.64(8) . . . . ? C15 C14 C19 C13 116.04(8) . . . . ? C13 C14 C19 C18 -117.75(8) . . . . ? C15 C14 C19 C18 -1.71(9) . . . . ? C20 C18 C19 C13 -28.31(10) . . . . ? C17 C18 C19 C13 -133.24(8) . . . . ? C20 C18 C19 C14 34.26(9) . . . . ? C17 C18 C19 C14 -70.67(8) . . . . ? C19 C18 C20 C15 -51.45(8) . . . . ? C17 C18 C20 C15 56.90(7) . . . . ? C14 C15 C20 C18 50.52(8) . . . . ? C16 C15 C20 C18 -57.95(7) . . . . ? O1 S1 C21 C26 -27.71(9) . . . . ? O2 S1 C21 C26 -157.07(7) . . . . ? C1 S1 C21 C26 90.99(8) . . . . ? O1 S1 C21 C22 147.60(7) . . . . ? O2 S1 C21 C22 18.23(8) . . . . ? C1 S1 C21 C22 -93.70(7) . . . . ? C26 C21 C22 C23 -1.37(14) . . . . ? S1 C21 C22 C23 -176.65(7) . . . . ? C21 C22 C23 C24 0.71(15) . . . . ? C22 C23 C24 C25 0.17(17) . . . . ? C23 C24 C25 C26 -0.42(17) . . . . ? C24 C25 C26 C21 -0.22(16) . . . . ? C22 C21 C26 C25 1.13(14) . . . . ? S1 C21 C26 C25 176.28(8) . . . . ? O3 S2 C27 C28 -20.58(9) . . . . ? O4 S2 C27 C28 -150.25(7) . . . . ? C1 S2 C27 C28 96.86(8) . . . . ? O3 S2 C27 C32 154.63(7) . . . . ? O4 S2 C27 C32 24.96(9) . . . . ? C1 S2 C27 C32 -87.93(8) . . . . ? C32 C27 C28 C29 1.84(14) . . . . ? S2 C27 C28 C29 176.92(8) . . . . ? C27 C28 C29 C30 0.61(15) . . . . ? C28 C29 C30 C31 -2.16(16) . . . . ? C29 C30 C31 C32 1.26(16) . . . . ? C30 C31 C32 C27 1.15(15) . . . . ? C28 C27 C32 C31 -2.73(15) . . . . ? S2 C27 C32 C31 -177.84(8) . . . . ? _diffrn_measured_fraction_theta_max 0.927 _diffrn_reflns_theta_full 36.35 _diffrn_measured_fraction_theta_full 0.927 _refine_diff_density_max 0.517 _refine_diff_density_min -0.443 _refine_diff_density_rms 0.071 # Attachment 'web_deposit_cif_file_6_AntonioM.Echavarren_1276529606.cif' data_dhog14_0m _database_code_depnum_ccdc_archive 'CCDC 780821' #TrackingRef 'web_deposit_cif_file_6_AntonioM.Echavarren_1276529606.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H34 O4 S2' _chemical_formula_weight 558.72 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' 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 10.7285(12) _cell_length_b 10.9833(12) _cell_length_c 13.0463(12) _cell_angle_alpha 111.389(5) _cell_angle_beta 92.772(5) _cell_angle_gamma 103.536(6) _cell_volume 1376.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 467 _cell_measurement_theta_min 2.79 _cell_measurement_theta_max 30.29 _exptl_crystal_description BLock _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.348 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.232 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9773 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details ; SADABS Version 2008/1 Bruker-Nonius Blessing, Acta Cryst. (1995) A51 33-38 ; _exptl_special_details ; It should be noted that the esd's of the cell dimensions are probably too low; they should be multiplied by a factor of 2 to 10 ; _diffrn_ambient_temperature 100(2) _diffrn_measurement_specimen_suppport 'magnetic support whith 10 micron nylon fiber cryoloop' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'rotating anode X-ray tube' _diffrn_source_type 'Bruker-Nonius FR 591' _diffrn_source_power 50 _diffrn_source_current 70 _diffrn_source_size '3 mm x 0.3 mm fine focus' _diffrn_radiation_monochromator 'Multilayer Montel 200 mirrors' _diffrn_detector_type '4K CCD area detector APEX II' _diffrn_measurement_device_type 'Kappa 4-axis goniometer bruker-nonius' _diffrn_measurement_method ; Fullsphere data collection, phi and omega scans ; _diffrn_detector_area_resol_mean 512 _diffrn_reflns_number 18615 _diffrn_reflns_av_R_equivalents 0.0825 _diffrn_reflns_av_sigmaI/netI 0.1115 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 30.29 _reflns_number_total 7467 _reflns_number_gt 5081 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 v2008.6-1' _computing_cell_refinement 'Bruker APEX2 v2008.6-1' _computing_data_reduction 'Bruker SAINT V7.60A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXS-97 (Sheldrick, 2008)' _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^)+(0.0856P)^2^+1.7473P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7467 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1108 _refine_ls_R_factor_gt 0.0729 _refine_ls_wR_factor_ref 0.2100 _refine_ls_wR_factor_gt 0.1838 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 0.64084(6) 0.76401(8) 0.25745(6) 0.01526(17) Uani 1 1 d . . . C1 C 0.7567(3) 0.7903(3) 0.1631(2) 0.0143(5) Uani 1 1 d . . . O1 O 0.5291(2) 0.6628(2) 0.18396(18) 0.0216(5) Uani 1 1 d . . . S2 S 0.92221(7) 0.88111(8) 0.23535(6) 0.01639(18) Uani 1 1 d . . . C2 C 0.7515(3) 0.6471(3) 0.0742(2) 0.0166(6) Uani 1 1 d . . . H2A H 0.8384 0.6380 0.0644 0.020 Uiso 1 1 calc R . . H2B H 0.7058 0.5762 0.0971 0.020 Uiso 1 1 calc R . . O2 O 0.7040(2) 0.7345(3) 0.34190(17) 0.0207(5) Uani 1 1 d . . . C3 C 0.6800(3) 0.6369(3) -0.0333(2) 0.0161(6) Uani 1 1 d . . . H3 H 0.6139 0.5528 -0.0786 0.019 Uiso 1 1 calc R . . O3 O 0.9170(2) 0.9996(2) 0.32919(18) 0.0218(5) Uani 1 1 d . . . C4 C 0.7556(3) 0.7223(3) -0.0900(2) 0.0155(6) Uani 1 1 d . . . H4 H 0.8455 0.7688 -0.0544 0.019 Uiso 1 1 calc R . . O4 O 0.9942(2) 0.8977(2) 0.14889(18) 0.0218(5) Uani 1 1 d . . . C5 C 0.6552(3) 0.7713(3) -0.0184(2) 0.0158(6) Uani 1 1 d . . . C6 C 0.7119(3) 0.8727(3) 0.1003(2) 0.0167(6) Uani 1 1 d . . . H6A H 0.6469 0.9143 0.1364 0.020 Uiso 1 1 calc R . . H6B H 0.7848 0.9437 0.0995 0.020 Uiso 1 1 calc R . . C7 C 0.5356(3) 0.7879(3) -0.0693(2) 0.0155(5) Uani 1 1 d . . . H7 H 0.5490 0.8737 -0.0798 0.019 Uiso 1 1 calc R . . C8 C 0.4301(3) 0.6725(3) -0.1538(2) 0.0165(6) Uani 1 1 d . . . H8 H 0.4432 0.5823 -0.1704 0.020 Uiso 1 1 calc R . . C9 C 0.3713(3) 0.6909(4) -0.2532(2) 0.0227(7) Uani 1 1 d . . . H9A H 0.4189 0.6593 -0.3145 0.027 Uiso 1 1 calc R . . H9B H 0.3817 0.7870 -0.2344 0.027 Uiso 1 1 calc R . . C10 C 0.2259(3) 0.6148(4) -0.2922(3) 0.0304(8) Uani 1 1 d . . . H10A H 0.2111 0.5709 -0.3727 0.037 Uiso 1 1 calc R . . H10B H 0.2041 0.5443 -0.2628 0.037 Uiso 1 1 calc R . . C11 C 0.1370(3) 0.7062(4) -0.2560(3) 0.0274(8) Uani 1 1 d . . . H11 H 0.0972 0.7260 -0.3106 0.033 Uiso 1 1 calc R . . C12 C 0.1107(3) 0.7606(4) -0.1538(3) 0.0235(7) Uani 1 1 d . . . H12 H 0.0531 0.8141 -0.1430 0.028 Uiso 1 1 calc R . . C13 C 0.1661(3) 0.7433(4) -0.0537(3) 0.0249(7) Uani 1 1 d . . . H13A H 0.1609 0.6481 -0.0725 0.030 Uiso 1 1 calc R . . H13B H 0.1149 0.7710 0.0056 0.030 Uiso 1 1 calc R . . C14 C 0.3100(3) 0.8286(4) -0.0120(3) 0.0221(7) Uani 1 1 d . . . H14A H 0.3304 0.8934 -0.0472 0.027 Uiso 1 1 calc R . . H14B H 0.3208 0.8793 0.0677 0.027 Uiso 1 1 calc R . . C15 C 0.4040(3) 0.7411(3) -0.0370(2) 0.0170(6) Uani 1 1 d . . . H15 H 0.4035 0.6877 0.0089 0.020 Uiso 1 1 calc R . . C16 C 0.5891(3) 0.9119(3) 0.3207(2) 0.0171(6) Uani 1 1 d . . . C17 C 0.4684(3) 0.9135(4) 0.2783(3) 0.0230(7) Uani 1 1 d . . . H17 H 0.4204 0.8409 0.2153 0.028 Uiso 1 1 calc R . . C18 C 0.4197(3) 1.0231(4) 0.3299(3) 0.0290(8) Uani 1 1 d . . . H18 H 0.3394 1.0250 0.3013 0.035 Uiso 1 1 calc R . . C19 C 0.4916(3) 1.1305(4) 0.4246(3) 0.0277(8) Uani 1 1 d . . . H19 H 0.4591 1.2043 0.4597 0.033 Uiso 1 1 calc R . . C20 C 0.6114(3) 1.1277(4) 0.4669(3) 0.0266(8) Uani 1 1 d . . . H20 H 0.6587 1.2001 0.5303 0.032 Uiso 1 1 calc R . . C21 C 0.6619(3) 1.0187(4) 0.4161(3) 0.0235(7) Uani 1 1 d . . . H21 H 0.7422 1.0169 0.4449 0.028 Uiso 1 1 calc R . . C22 C 0.9856(3) 0.7755(3) 0.2853(2) 0.0180(6) Uani 1 1 d . . . C23 C 0.9818(3) 0.7900(4) 0.3957(2) 0.0241(7) Uani 1 1 d . . . H23 H 0.9449 0.8539 0.4429 0.029 Uiso 1 1 calc R . . C24 C 1.0339(3) 0.7076(4) 0.4338(3) 0.0300(8) Uani 1 1 d . . . H24 H 1.0320 0.7165 0.5073 0.036 Uiso 1 1 calc R . . C25 C 1.0888(3) 0.6121(4) 0.3640(3) 0.0305(8) Uani 1 1 d . . . H25 H 1.1214 0.5561 0.3904 0.037 Uiso 1 1 calc R . . C26 C 1.0953(3) 0.5999(4) 0.2543(3) 0.0281(8) Uani 1 1 d . . . H26 H 1.1336 0.5369 0.2080 0.034 Uiso 1 1 calc R . . C27 C 1.0447(3) 0.6815(4) 0.2149(3) 0.0234(7) Uani 1 1 d . . . H27 H 1.0495 0.6746 0.1421 0.028 Uiso 1 1 calc R . . C28 C 0.7355(3) 0.6858(3) -0.2131(2) 0.0157(6) Uani 1 1 d . . . C29 C 0.6599(3) 0.5602(3) -0.2894(2) 0.0176(6) Uani 1 1 d . . . H29 H 0.6196 0.4938 -0.2643 0.021 Uiso 1 1 calc R . . C30 C 0.6447(3) 0.5336(3) -0.4030(2) 0.0188(6) Uani 1 1 d . . . H30 H 0.5921 0.4506 -0.4530 0.023 Uiso 1 1 calc R . . C31 C 0.7073(3) 0.6299(4) -0.4419(2) 0.0209(6) Uani 1 1 d . . . H31 H 0.6983 0.6111 -0.5178 0.025 Uiso 1 1 calc R . . C32 C 0.7837(3) 0.7547(4) -0.3666(2) 0.0217(6) Uani 1 1 d . . . H32 H 0.8259 0.8200 -0.3920 0.026 Uiso 1 1 calc R . . C33 C 0.7971(3) 0.7821(3) -0.2531(2) 0.0193(6) Uani 1 1 d . . . H33 H 0.8480 0.8661 -0.2033 0.023 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 0.0174(3) 0.0147(4) 0.0140(3) 0.0067(3) 0.0013(2) 0.0034(3) C1 0.0196(12) 0.0113(14) 0.0114(11) 0.0038(10) 0.0010(9) 0.0043(10) O1 0.0205(10) 0.0173(12) 0.0224(10) 0.0057(9) 0.0003(8) 0.0007(8) S2 0.0171(3) 0.0157(4) 0.0143(3) 0.0044(3) 0.0021(2) 0.0031(3) C2 0.0233(13) 0.0123(15) 0.0138(12) 0.0039(11) 0.0007(10) 0.0066(10) O2 0.0232(10) 0.0260(13) 0.0192(10) 0.0150(10) 0.0027(8) 0.0082(9) C3 0.0170(12) 0.0175(15) 0.0122(11) 0.0050(11) 0.0005(9) 0.0035(10) O3 0.0216(10) 0.0169(12) 0.0183(10) -0.0006(9) 0.0012(8) 0.0021(8) C4 0.0171(12) 0.0161(15) 0.0120(11) 0.0053(11) 0.0020(9) 0.0024(10) O4 0.0224(10) 0.0223(13) 0.0214(10) 0.0103(9) 0.0062(8) 0.0036(9) C5 0.0185(12) 0.0152(15) 0.0123(11) 0.0042(11) 0.0021(10) 0.0036(10) C6 0.0213(13) 0.0156(15) 0.0131(12) 0.0052(11) 0.0012(10) 0.0057(11) C7 0.0196(12) 0.0115(14) 0.0169(12) 0.0073(11) 0.0015(10) 0.0040(10) C8 0.0181(12) 0.0173(15) 0.0126(12) 0.0037(11) 0.0026(10) 0.0057(10) C9 0.0210(13) 0.033(2) 0.0150(13) 0.0081(13) 0.0028(10) 0.0099(12) C10 0.0241(15) 0.039(2) 0.0203(15) 0.0009(15) -0.0027(12) 0.0120(14) C11 0.0219(14) 0.034(2) 0.0243(15) 0.0079(15) -0.0033(12) 0.0113(13) C12 0.0174(13) 0.0255(19) 0.0286(16) 0.0108(14) 0.0012(11) 0.0074(12) C13 0.0220(14) 0.035(2) 0.0241(15) 0.0150(14) 0.0100(12) 0.0128(13) C14 0.0264(15) 0.0227(18) 0.0172(13) 0.0039(13) 0.0020(11) 0.0126(12) C15 0.0193(13) 0.0188(16) 0.0143(12) 0.0063(11) 0.0038(10) 0.0078(11) C16 0.0217(13) 0.0149(15) 0.0162(12) 0.0070(11) 0.0053(10) 0.0053(11) C17 0.0256(15) 0.0262(19) 0.0175(13) 0.0067(13) 0.0025(11) 0.0107(13) C18 0.0328(17) 0.033(2) 0.0277(16) 0.0121(15) 0.0089(14) 0.0189(15) C19 0.0349(17) 0.0235(19) 0.0308(17) 0.0126(15) 0.0162(14) 0.0137(14) C20 0.0290(16) 0.0200(18) 0.0255(15) 0.0043(14) 0.0099(13) 0.0030(13) C21 0.0216(14) 0.0243(18) 0.0205(14) 0.0068(13) 0.0053(11) 0.0014(12) C22 0.0161(12) 0.0190(16) 0.0182(13) 0.0072(12) -0.0005(10) 0.0041(11) C23 0.0189(13) 0.035(2) 0.0160(13) 0.0081(13) -0.0007(10) 0.0059(13) C24 0.0240(15) 0.048(3) 0.0218(15) 0.0176(16) -0.0008(12) 0.0101(15) C25 0.0260(16) 0.036(2) 0.0375(19) 0.0237(17) -0.0025(14) 0.0090(14) C26 0.0256(15) 0.032(2) 0.0289(16) 0.0112(15) 0.0015(13) 0.0136(14) C27 0.0215(14) 0.0283(19) 0.0205(14) 0.0074(13) 0.0023(11) 0.0105(12) C28 0.0165(12) 0.0190(16) 0.0133(12) 0.0074(11) 0.0028(9) 0.0062(10) C29 0.0196(13) 0.0183(16) 0.0153(12) 0.0067(12) 0.0038(10) 0.0050(11) C30 0.0216(13) 0.0191(16) 0.0133(12) 0.0021(12) -0.0003(10) 0.0088(11) C31 0.0266(14) 0.0286(19) 0.0136(12) 0.0093(12) 0.0064(11) 0.0160(13) C32 0.0269(14) 0.0246(18) 0.0195(14) 0.0129(13) 0.0072(11) 0.0097(12) C33 0.0176(12) 0.0207(16) 0.0180(13) 0.0061(12) 0.0034(10) 0.0043(11) _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 1.439(2) . ? S1 O1 1.442(2) . ? S1 C16 1.765(3) . ? S1 C1 1.840(3) . ? C1 C6 1.558(4) . ? C1 C2 1.563(4) . ? C1 S2 1.833(3) . ? S2 O4 1.439(2) . ? S2 O3 1.440(2) . ? S2 C22 1.764(4) . ? C2 C3 1.519(4) . ? C3 C5 1.506(5) . ? C3 C4 1.515(4) . ? C4 C28 1.498(4) . ? C4 C5 1.525(4) . ? C5 C7 1.494(4) . ? C5 C6 1.531(4) . ? C7 C8 1.515(4) . ? C7 C15 1.519(4) . ? C8 C15 1.507(4) . ? C8 C9 1.513(4) . ? C9 C10 1.547(4) . ? C10 C11 1.513(5) . ? C11 C12 1.323(4) . ? C12 C13 1.501(5) . ? C13 C14 1.558(5) . ? C14 C15 1.518(4) . ? C16 C17 1.390(4) . ? C16 C21 1.395(4) . ? C17 C18 1.383(5) . ? C18 C19 1.390(5) . ? C19 C20 1.386(5) . ? C20 C21 1.388(5) . ? C22 C23 1.394(4) . ? C22 C27 1.407(4) . ? C23 C24 1.384(6) . ? C24 C25 1.386(6) . ? C25 C26 1.394(5) . ? C26 C27 1.379(5) . ? C28 C33 1.392(4) . ? C28 C29 1.396(4) . ? C29 C30 1.396(4) . ? C30 C31 1.386(5) . ? C31 C32 1.389(5) . ? C32 C33 1.392(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S1 O1 118.63(15) . . ? O2 S1 C16 109.47(14) . . ? O1 S1 C16 105.86(14) . . ? O2 S1 C1 108.63(13) . . ? O1 S1 C1 103.94(12) . . ? C16 S1 C1 110.04(14) . . ? C6 C1 C2 107.4(2) . . ? C6 C1 S2 108.54(19) . . ? C2 C1 S2 111.1(2) . . ? C6 C1 S1 109.42(19) . . ? C2 C1 S1 107.14(19) . . ? S2 C1 S1 113.08(14) . . ? O4 S2 O3 119.28(14) . . ? O4 S2 C22 107.16(14) . . ? O3 S2 C22 108.42(15) . . ? O4 S2 C1 104.11(13) . . ? O3 S2 C1 108.34(13) . . ? C22 S2 C1 109.19(14) . . ? C3 C2 C1 106.2(3) . . ? C5 C3 C4 60.64(19) . . ? C5 C3 C2 109.8(2) . . ? C4 C3 C2 115.1(2) . . ? C28 C4 C3 123.6(2) . . ? C28 C4 C5 121.1(3) . . ? C3 C4 C5 59.40(19) . . ? C7 C5 C3 124.8(2) . . ? C7 C5 C4 120.6(2) . . ? C3 C5 C4 60.0(2) . . ? C7 C5 C6 116.3(3) . . ? C3 C5 C6 108.8(2) . . ? C4 C5 C6 114.4(2) . . ? C5 C6 C1 106.4(2) . . ? C5 C7 C8 124.5(3) . . ? C5 C7 C15 121.1(3) . . ? C8 C7 C15 59.55(18) . . ? C15 C8 C9 123.2(3) . . ? C15 C8 C7 60.39(18) . . ? C9 C8 C7 119.6(3) . . ? C8 C9 C10 114.0(3) . . ? C11 C10 C9 113.4(3) . . ? C12 C11 C10 126.0(3) . . ? C11 C12 C13 125.4(3) . . ? C12 C13 C14 111.8(3) . . ? C15 C14 C13 112.5(3) . . ? C8 C15 C14 121.6(3) . . ? C8 C15 C7 60.06(18) . . ? C14 C15 C7 122.0(3) . . ? C17 C16 C21 121.0(3) . . ? C17 C16 S1 117.8(2) . . ? C21 C16 S1 120.9(3) . . ? C18 C17 C16 119.9(3) . . ? C17 C18 C19 119.6(3) . . ? C20 C19 C18 120.2(3) . . ? C19 C20 C21 121.0(3) . . ? C20 C21 C16 118.3(3) . . ? C23 C22 C27 120.6(3) . . ? C23 C22 S2 119.6(3) . . ? C27 C22 S2 119.8(2) . . ? C24 C23 C22 118.7(3) . . ? C23 C24 C25 121.0(3) . . ? C24 C25 C26 120.2(4) . . ? C27 C26 C25 119.7(3) . . ? C26 C27 C22 119.7(3) . . ? C33 C28 C29 118.6(3) . . ? C33 C28 C4 117.9(3) . . ? C29 C28 C4 123.5(3) . . ? C28 C29 C30 120.3(3) . . ? C31 C30 C29 120.5(3) . . ? C30 C31 C32 119.4(3) . . ? C31 C32 C33 120.0(3) . . ? C32 C33 C28 121.1(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 S1 C1 C6 -159.12(19) . . . . ? O1 S1 C1 C6 73.7(2) . . . . ? C16 S1 C1 C6 -39.3(2) . . . . ? O2 S1 C1 C2 84.7(2) . . . . ? O1 S1 C1 C2 -42.5(2) . . . . ? C16 S1 C1 C2 -155.5(2) . . . . ? O2 S1 C1 S2 -38.0(2) . . . . ? O1 S1 C1 S2 -165.22(17) . . . . ? C16 S1 C1 S2 81.8(2) . . . . ? C6 C1 S2 O4 -55.1(2) . . . . ? C2 C1 S2 O4 62.8(2) . . . . ? S1 C1 S2 O4 -176.73(17) . . . . ? C6 C1 S2 O3 72.8(2) . . . . ? C2 C1 S2 O3 -169.3(2) . . . . ? S1 C1 S2 O3 -48.8(2) . . . . ? C6 C1 S2 C22 -169.30(18) . . . . ? C2 C1 S2 C22 -51.4(2) . . . . ? S1 C1 S2 C22 69.09(19) . . . . ? C6 C1 C2 C3 -10.9(3) . . . . ? S2 C1 C2 C3 -129.5(2) . . . . ? S1 C1 C2 C3 106.6(2) . . . . ? C1 C2 C3 C5 6.5(3) . . . . ? C1 C2 C3 C4 72.5(3) . . . . ? C5 C3 C4 C28 -109.1(3) . . . . ? C2 C3 C4 C28 151.3(3) . . . . ? C2 C3 C4 C5 -99.6(3) . . . . ? C4 C3 C5 C7 108.3(3) . . . . ? C2 C3 C5 C7 -143.4(3) . . . . ? C2 C3 C5 C4 108.4(2) . . . . ? C4 C3 C5 C6 -107.9(2) . . . . ? C2 C3 C5 C6 0.5(3) . . . . ? C28 C4 C5 C7 -1.8(4) . . . . ? C3 C4 C5 C7 -115.1(3) . . . . ? C28 C4 C5 C3 113.3(3) . . . . ? C28 C4 C5 C6 -148.3(3) . . . . ? C3 C4 C5 C6 98.4(3) . . . . ? C7 C5 C6 C1 140.0(2) . . . . ? C3 C5 C6 C1 -7.3(3) . . . . ? C4 C5 C6 C1 -72.1(3) . . . . ? C2 C1 C6 C5 11.2(3) . . . . ? S2 C1 C6 C5 131.42(19) . . . . ? S1 C1 C6 C5 -104.8(2) . . . . ? C3 C5 C7 C8 -7.7(4) . . . . ? C4 C5 C7 C8 65.0(4) . . . . ? C6 C5 C7 C8 -149.2(3) . . . . ? C3 C5 C7 C15 64.6(4) . . . . ? C4 C5 C7 C15 137.3(3) . . . . ? C6 C5 C7 C15 -76.9(4) . . . . ? C5 C7 C8 C15 108.8(3) . . . . ? C5 C7 C8 C9 -137.5(3) . . . . ? C15 C7 C8 C9 113.7(3) . . . . ? C15 C8 C9 C10 -74.3(4) . . . . ? C7 C8 C9 C10 -146.4(3) . . . . ? C8 C9 C10 C11 102.4(4) . . . . ? C9 C10 C11 C12 -73.1(5) . . . . ? C10 C11 C12 C13 1.0(6) . . . . ? C11 C12 C13 C14 74.6(5) . . . . ? C12 C13 C14 C15 -107.6(3) . . . . ? C9 C8 C15 C14 3.4(5) . . . . ? C7 C8 C15 C14 111.3(3) . . . . ? C9 C8 C15 C7 -107.9(3) . . . . ? C13 C14 C15 C8 71.4(4) . . . . ? C13 C14 C15 C7 143.6(3) . . . . ? C5 C7 C15 C8 -114.4(3) . . . . ? C5 C7 C15 C14 134.8(3) . . . . ? C8 C7 C15 C14 -110.7(3) . . . . ? O2 S1 C16 C17 -139.6(2) . . . . ? O1 S1 C16 C17 -10.6(3) . . . . ? C1 S1 C16 C17 101.1(3) . . . . ? O2 S1 C16 C21 35.0(3) . . . . ? O1 S1 C16 C21 163.9(2) . . . . ? C1 S1 C16 C21 -84.4(3) . . . . ? C21 C16 C17 C18 1.0(5) . . . . ? S1 C16 C17 C18 175.5(3) . . . . ? C16 C17 C18 C19 -0.6(5) . . . . ? C17 C18 C19 C20 0.2(5) . . . . ? C18 C19 C20 C21 0.0(5) . . . . ? C19 C20 C21 C16 0.3(5) . . . . ? C17 C16 C21 C20 -0.8(5) . . . . ? S1 C16 C21 C20 -175.1(2) . . . . ? O4 S2 C22 C23 150.4(2) . . . . ? O3 S2 C22 C23 20.4(3) . . . . ? C1 S2 C22 C23 -97.5(3) . . . . ? O4 S2 C22 C27 -26.8(3) . . . . ? O3 S2 C22 C27 -156.8(2) . . . . ? C1 S2 C22 C27 85.3(3) . . . . ? C27 C22 C23 C24 -1.8(5) . . . . ? S2 C22 C23 C24 -179.0(3) . . . . ? C22 C23 C24 C25 -0.1(5) . . . . ? C23 C24 C25 C26 1.6(5) . . . . ? C24 C25 C26 C27 -1.2(5) . . . . ? C25 C26 C27 C22 -0.7(5) . . . . ? C23 C22 C27 C26 2.2(5) . . . . ? S2 C22 C27 C26 179.4(3) . . . . ? C3 C4 C28 C33 170.7(3) . . . . ? C5 C4 C28 C33 98.9(3) . . . . ? C3 C4 C28 C29 -10.2(5) . . . . ? C5 C4 C28 C29 -81.9(4) . . . . ? C33 C28 C29 C30 -1.4(4) . . . . ? C4 C28 C29 C30 179.5(3) . . . . ? C28 C29 C30 C31 1.9(5) . . . . ? C29 C30 C31 C32 -1.3(5) . . . . ? C30 C31 C32 C33 0.1(5) . . . . ? C31 C32 C33 C28 0.4(5) . . . . ? C29 C28 C33 C32 0.2(5) . . . . ? C4 C28 C33 C32 179.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.905 _diffrn_reflns_theta_full 30.29 _diffrn_measured_fraction_theta_full 0.905 _refine_diff_density_max 0.539 _refine_diff_density_min -0.600 _refine_diff_density_rms 0.106