Supplementary Material for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Nathaniel Finney' 'Judith M. Mitchell' _publ_contact_author_name 'Nathaniel Finney' _publ_contact_author_address ; Organisch-Chemisches Institut Universitat Zurich Winterthurerstrasse 190 Zurich CH-8057 SWITZERLAND ; _publ_contact_author_email FINNEY@UNIZH.CH _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Synthetic studies of pseurotin A: Preparation of an advanced lactam aldehyde intermediate. ; data_jmich01 _database_code_depnum_ccdc_archive 'CCDC 283232' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H27 N O7 S' _chemical_formula_weight 473.53 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.9592(7) _cell_length_b 9.2569(6) _cell_length_c 15.3512(11) _cell_angle_alpha 79.4720(10) _cell_angle_beta 83.1290(10) _cell_angle_gamma 69.3510(10) _cell_volume 1169.19(15) _cell_formula_units_Z 2 _cell_measurement_temperature 218(2) _cell_measurement_reflns_used 4557 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 28.24 _exptl_crystal_description blocks _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 500 _exptl_absorpt_coefficient_mu 0.183 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.9303 _exptl_absorpt_correction_T_max 0.9819 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 218(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7140 _diffrn_reflns_av_R_equivalents 0.0196 _diffrn_reflns_av_sigmaI/netI 0.0366 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.35 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4097 _reflns_number_gt 3434 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0772P)^2^+1.0148P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4097 _refine_ls_number_parameters 302 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0713 _refine_ls_R_factor_gt 0.0596 _refine_ls_wR_factor_ref 0.1614 _refine_ls_wR_factor_gt 0.1529 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N -0.0628(3) 0.9094(3) 0.10731(15) 0.0333(6) Uani 1 1 d . . . S1 S 0.52235(10) 0.52304(10) 0.22728(6) 0.0516(3) Uani 1 1 d . . . O1 O -0.1913(3) 1.0899(2) 0.22976(14) 0.0432(5) Uani 1 1 d . . . O2 O -0.2796(2) 0.8156(2) 0.14434(13) 0.0358(5) Uani 1 1 d . . . O3 O 0.0109(2) 0.72829(19) 0.29644(11) 0.0286(4) Uani 1 1 d . . . O4 O 0.0584(3) 0.3994(2) 0.15292(15) 0.0467(6) Uani 1 1 d . . . O5 O 0.2591(5) 0.2674(4) 0.0694(2) 0.1124(15) Uani 1 1 d . . . O6 O 0.1642(3) 0.8141(2) 0.02128(14) 0.0513(6) Uani 1 1 d . . . O7 O 0.2402(2) 0.5671(2) 0.17795(13) 0.0329(4) Uani 1 1 d . . . C1 C -0.1613(3) 0.8560(3) 0.17716(17) 0.0290(6) Uani 1 1 d . . . C2 C -0.0451(3) 0.7007(3) 0.22177(16) 0.0276(6) Uani 1 1 d . . . H2A H -0.0999 0.6229 0.2395 0.033 Uiso 1 1 calc R . . C3 C 0.0864(3) 0.6489(3) 0.14783(17) 0.0307(6) Uani 1 1 d . . . C4 C 0.0705(3) 0.8002(3) 0.08400(18) 0.0359(7) Uani 1 1 d . . . C5 C -0.2376(3) 0.9809(3) 0.23856(18) 0.0296(6) Uani 1 1 d . . . C6 C -0.3707(3) 0.9686(3) 0.30330(17) 0.0302(6) Uani 1 1 d . . . C7 C -0.4671(4) 1.1029(3) 0.3362(2) 0.0411(7) Uani 1 1 d . . . H7A H -0.4463 1.1968 0.3176 0.049 Uiso 1 1 calc R . . C8 C -0.5931(4) 1.0993(4) 0.3961(2) 0.0504(8) Uani 1 1 d . . . H8A H -0.6585 1.1911 0.4179 0.061 Uiso 1 1 calc R . . C9 C -0.6240(4) 0.9629(4) 0.4242(2) 0.0479(8) Uani 1 1 d . . . H9A H -0.7091 0.9605 0.4661 0.058 Uiso 1 1 calc R . . C10 C -0.5311(4) 0.8310(4) 0.3913(2) 0.0476(8) Uani 1 1 d . . . H10A H -0.5529 0.7376 0.4102 0.057 Uiso 1 1 calc R . . C11 C -0.4054(4) 0.8327(3) 0.3305(2) 0.0417(7) Uani 1 1 d . . . H11A H -0.3430 0.7412 0.3076 0.050 Uiso 1 1 calc R . . C12 C -0.3892(4) 0.9397(4) 0.0908(2) 0.0494(8) Uani 1 1 d . . . H12A H -0.4663 0.9024 0.0713 0.074 Uiso 1 1 calc R . . H12B H -0.3317 0.9779 0.0394 0.074 Uiso 1 1 calc R . . H12C H -0.4445 1.0237 0.1249 0.074 Uiso 1 1 calc R . . C13 C 0.0601(4) 0.5924(3) 0.36191(18) 0.0355(6) Uani 1 1 d . . . H13A H 0.1522 0.5121 0.3381 0.043 Uiso 1 1 calc R . . H13B H -0.0270 0.5499 0.3781 0.043 Uiso 1 1 calc R . . C14 C 0.1040(3) 0.6359(3) 0.44180(17) 0.0311(6) Uani 1 1 d . . . C15 C 0.2448(3) 0.5474(3) 0.48129(19) 0.0368(7) Uani 1 1 d . . . H15A H 0.3161 0.4616 0.4561 0.044 Uiso 1 1 calc R . . C16 C 0.2818(4) 0.5839(3) 0.5574(2) 0.0401(7) Uani 1 1 d . . . H16A H 0.3778 0.5224 0.5839 0.048 Uiso 1 1 calc R . . C17 C 0.1802(4) 0.7080(4) 0.59443(19) 0.0415(7) Uani 1 1 d . . . H17A H 0.2053 0.7322 0.6465 0.050 Uiso 1 1 calc R . . C18 C 0.0404(4) 0.7978(4) 0.5550(2) 0.0492(8) Uani 1 1 d . . . H18A H -0.0300 0.8841 0.5800 0.059 Uiso 1 1 calc R . . C19 C 0.0032(4) 0.7623(4) 0.4797(2) 0.0448(8) Uani 1 1 d . . . H19A H -0.0926 0.8249 0.4533 0.054 Uiso 1 1 calc R . . C20 C 0.0503(4) 0.5413(4) 0.0961(2) 0.0426(7) Uani 1 1 d . . . H20A H -0.0566 0.5915 0.0735 0.051 Uiso 1 1 calc R . . H20B H 0.1280 0.5197 0.0454 0.051 Uiso 1 1 calc R . . C21 C 0.1669(4) 0.2690(4) 0.1328(2) 0.0557(9) Uani 1 1 d . . . C22 C 0.1689(5) 0.1322(4) 0.2014(3) 0.0641(10) Uani 1 1 d . . . H22A H 0.2509 0.0392 0.1844 0.096 Uiso 1 1 calc R . . H22B H 0.0656 0.1184 0.2066 0.096 Uiso 1 1 calc R . . H22C H 0.1913 0.1499 0.2581 0.096 Uiso 1 1 calc R . . C23 C 0.3322(4) 0.6553(3) 0.1955(2) 0.0423(7) Uani 1 1 d . . . H23A H 0.2786 0.7159 0.2433 0.051 Uiso 1 1 calc R . . H23B H 0.3443 0.7279 0.1424 0.051 Uiso 1 1 calc R . . C24 C 0.6098(5) 0.4628(5) 0.1236(3) 0.0806(13) Uani 1 1 d . . . H24A H 0.7169 0.3884 0.1316 0.121 Uiso 1 1 calc R . . H24B H 0.6149 0.5530 0.0814 0.121 Uiso 1 1 calc R . . H24C H 0.5453 0.4142 0.1013 0.121 Uiso 1 1 calc R . . H1A H -0.099(4) 0.994(4) 0.079(2) 0.034(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0321(13) 0.0309(12) 0.0259(12) 0.0065(10) -0.0003(10) -0.0030(10) S1 0.0432(5) 0.0525(5) 0.0582(6) 0.0014(4) -0.0169(4) -0.0155(4) O1 0.0463(12) 0.0376(11) 0.0501(13) -0.0096(10) 0.0079(10) -0.0215(10) O2 0.0336(11) 0.0417(11) 0.0325(10) -0.0060(8) -0.0100(8) -0.0107(9) O3 0.0355(10) 0.0281(9) 0.0217(9) 0.0002(7) -0.0053(8) -0.0107(8) O4 0.0489(13) 0.0403(11) 0.0560(14) -0.0214(10) 0.0097(11) -0.0185(10) O5 0.139(3) 0.0673(19) 0.068(2) -0.0069(16) 0.027(2) 0.0300(19) O6 0.0449(13) 0.0497(12) 0.0354(12) 0.0104(10) 0.0141(10) -0.0002(10) O7 0.0303(10) 0.0283(9) 0.0373(11) -0.0014(8) -0.0042(8) -0.0075(8) C1 0.0303(14) 0.0328(13) 0.0238(13) -0.0008(11) -0.0024(11) -0.0121(11) C2 0.0311(14) 0.0284(13) 0.0226(13) -0.0020(10) -0.0024(11) -0.0101(11) C3 0.0302(14) 0.0320(13) 0.0255(14) -0.0004(11) -0.0015(11) -0.0071(11) C4 0.0352(16) 0.0382(15) 0.0273(15) 0.0025(12) -0.0016(12) -0.0075(12) C5 0.0285(14) 0.0281(13) 0.0300(14) -0.0005(11) -0.0049(11) -0.0078(11) C6 0.0300(14) 0.0318(13) 0.0276(14) -0.0027(11) -0.0046(11) -0.0087(11) C7 0.0415(17) 0.0358(15) 0.0464(18) -0.0091(13) 0.0010(14) -0.0132(13) C8 0.0426(18) 0.0442(17) 0.058(2) -0.0181(16) 0.0102(16) -0.0058(14) C9 0.0329(16) 0.058(2) 0.0425(18) -0.0008(15) 0.0094(14) -0.0101(14) C10 0.0433(18) 0.0394(16) 0.054(2) 0.0039(14) 0.0084(15) -0.0150(14) C11 0.0417(17) 0.0322(15) 0.0453(18) -0.0041(13) 0.0082(14) -0.0099(13) C12 0.0364(17) 0.064(2) 0.0422(18) -0.0032(16) -0.0171(14) -0.0070(15) C13 0.0487(17) 0.0315(14) 0.0249(14) 0.0049(11) -0.0084(12) -0.0143(13) C14 0.0350(15) 0.0344(14) 0.0231(13) 0.0036(11) -0.0025(11) -0.0145(12) C15 0.0350(15) 0.0362(15) 0.0361(16) -0.0028(12) -0.0047(12) -0.0090(12) C16 0.0379(16) 0.0415(16) 0.0396(17) 0.0021(13) -0.0155(13) -0.0118(13) C17 0.0500(18) 0.0516(18) 0.0281(15) -0.0021(13) -0.0093(13) -0.0234(15) C18 0.052(2) 0.0499(18) 0.0388(18) -0.0147(15) -0.0047(15) -0.0037(15) C19 0.0372(17) 0.0510(18) 0.0351(17) -0.0071(14) -0.0102(13) 0.0015(14) C20 0.0450(18) 0.0499(18) 0.0334(16) -0.0140(14) -0.0025(13) -0.0129(14) C21 0.055(2) 0.051(2) 0.048(2) -0.0197(16) -0.0091(17) 0.0044(16) C22 0.061(2) 0.051(2) 0.082(3) -0.0120(19) -0.006(2) -0.0194(18) C23 0.0401(17) 0.0333(15) 0.0546(19) -0.0046(14) -0.0054(14) -0.0139(13) C24 0.060(3) 0.078(3) 0.082(3) -0.011(2) 0.014(2) -0.004(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C4 1.325(4) . ? N1 C1 1.435(3) . ? S1 C23 1.774(3) . ? S1 C24 1.782(4) . ? O1 C5 1.200(3) . ? O2 C1 1.412(3) . ? O2 C12 1.419(4) . ? O3 C2 1.402(3) . ? O3 C13 1.428(3) . ? O4 C21 1.317(4) . ? O4 C20 1.421(4) . ? O5 C21 1.197(5) . ? O6 C4 1.219(3) . ? O7 C3 1.405(3) . ? O7 C23 1.424(3) . ? C1 C2 1.541(4) . ? C1 C5 1.542(4) . ? C2 C3 1.545(4) . ? C3 C20 1.519(4) . ? C3 C4 1.527(4) . ? C5 C6 1.481(4) . ? C6 C11 1.380(4) . ? C6 C7 1.384(4) . ? C7 C8 1.373(4) . ? C8 C9 1.370(5) . ? C9 C10 1.359(5) . ? C10 C11 1.376(4) . ? C13 C14 1.493(4) . ? C14 C15 1.379(4) . ? C14 C19 1.378(4) . ? C15 C16 1.380(4) . ? C16 C17 1.360(4) . ? C17 C18 1.374(5) . ? C18 C19 1.365(4) . ? C21 C22 1.488(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 N1 C1 115.1(2) . . ? C23 S1 C24 100.88(19) . . ? C1 O2 C12 114.7(2) . . ? C2 O3 C13 112.69(19) . . ? C21 O4 C20 118.2(3) . . ? C3 O7 C23 118.1(2) . . ? O2 C1 N1 112.3(2) . . ? O2 C1 C2 105.3(2) . . ? N1 C1 C2 103.3(2) . . ? O2 C1 C5 110.8(2) . . ? N1 C1 C5 110.0(2) . . ? C2 C1 C5 114.9(2) . . ? O3 C2 C1 108.7(2) . . ? O3 C2 C3 113.7(2) . . ? C1 C2 C3 103.6(2) . . ? O7 C3 C20 105.8(2) . . ? O7 C3 C4 115.0(2) . . ? C20 C3 C4 106.4(2) . . ? O7 C3 C2 114.7(2) . . ? C20 C3 C2 111.2(2) . . ? C4 C3 C2 103.6(2) . . ? O6 C4 N1 126.8(3) . . ? O6 C4 C3 124.7(3) . . ? N1 C4 C3 108.4(2) . . ? O1 C5 C6 121.6(2) . . ? O1 C5 C1 118.5(2) . . ? C6 C5 C1 119.8(2) . . ? C11 C6 C7 118.8(3) . . ? C11 C6 C5 123.8(2) . . ? C7 C6 C5 117.4(2) . . ? C8 C7 C6 120.2(3) . . ? C9 C8 C7 120.5(3) . . ? C10 C9 C8 119.6(3) . . ? C9 C10 C11 120.7(3) . . ? C10 C11 C6 120.2(3) . . ? O3 C13 C14 108.9(2) . . ? C15 C14 C19 118.2(3) . . ? C15 C14 C13 120.6(3) . . ? C19 C14 C13 121.1(3) . . ? C14 C15 C16 120.5(3) . . ? C17 C16 C15 120.5(3) . . ? C16 C17 C18 119.4(3) . . ? C19 C18 C17 120.4(3) . . ? C18 C19 C14 121.0(3) . . ? O4 C20 C3 109.1(2) . . ? O5 C21 O4 122.1(4) . . ? O5 C21 C22 125.6(3) . . ? O4 C21 C22 112.1(3) . . ? O7 C23 S1 108.14(18) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A O6 0.80(3) 2.08(3) 2.867(3) 166(3) 2_575 N1 H1A N1 0.80(3) 3.17(3) 3.655(5) 122(2) 2_575 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.775 _refine_diff_density_min -0.453 _refine_diff_density_rms 0.054