# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'R. Stockman' 'D. Hughes' 'Stephen J. Roe' _publ_contact_author_name 'Robert Stockman' _publ_contact_author_address ; School of Chemistry University of Nottingham University Park Nottingham NG7 2RD UNITED KINGDOM ; _publ_contact_author_email ROBERT.STOCKMAN@NOTTINGHAM.AC.UK _publ_requested_journal 'Chemical Communications' _publ_section_title ; A Two-Directional Approach to the Anatoxin Alkaloids: Second Synthesis of Homoanatoxin and Efficient Synthesis of Anatoxin-a ; data_stephenr3 _database_code_depnum_ccdc_archive 'CCDC 681986' _audit_creation_method 'SHELXL-97 and CrysAlis RED' _chemical_name_systematic ; ? ; _chemical_name_common 'Compound 12' _chemical_melting_point ? _chemical_formula_moiety 'C17 H21 N O3 S' _chemical_formula_structural p-tolyl-SO2-NC8H11-COMe _chemical_formula_sum 'C17 H21 N O3 S' _chemical_formula_weight 319.41 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 8.1733(9) _cell_length_b 8.2597(13) _cell_length_c 12.6277(13) _cell_angle_alpha 84.340(10) _cell_angle_beta 80.847(9) _cell_angle_gamma 66.033(13) _cell_volume 768.52(17) _cell_formula_units_Z 2 _cell_measurement_temperature 140(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'irregular block' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.380 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 340 _exptl_absorpt_coefficient_mu 0.223 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.896 _exptl_absorpt_correction_T_max 1.094 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28c4 beta Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 140(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type Mo-K\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur 3/CCD' _diffrn_measurement_method 'Thin slice \f and \w scans' _diffrn_detector_area_resol_mean 16.0050 _diffrn_reflns_number 10373 _diffrn_reflns_av_R_equivalents 0.0524 _diffrn_reflns_av_sigmaI/netI 0.0426 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.99 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3504 _reflns_number_gt 2916 _reflns_threshold_expression I>2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.28c4 beta ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28c4 beta ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28c4 beta ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997a)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997b)' _computing_molecular_graphics 'ORTEP (Johnson, 1971)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997b)' _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^)+(0.0593P)^2^+0.2138P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3504 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0518 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.1086 _refine_ls_wR_factor_gt 0.1031 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 0.59734(5) 0.20083(5) 0.15139(3) 0.02145(12) Uani 1 1 d . . . O1 O 0.69925(15) 0.02857(14) 0.19532(10) 0.0274(3) Uani 1 1 d . . . O2 O 0.64292(16) 0.24718(16) 0.04160(9) 0.0291(3) Uani 1 1 d . . . N1 N 0.39012(17) 0.22075(17) 0.16299(10) 0.0215(3) Uani 1 1 d . . . C2 C 0.2968(2) 0.1893(2) 0.26718(12) 0.0205(3) Uani 1 1 d . . . H2 H 0.3825 0.1348 0.3194 0.025 Uiso 1 1 calc R . . C3 C 0.1971(2) 0.07349(19) 0.25467(13) 0.0206(3) Uani 1 1 d . . . C31 C 0.1712(2) -0.0308(2) 0.35423(13) 0.0240(3) Uani 1 1 d . . . O31 O 0.22148(18) -0.01181(17) 0.43681(10) 0.0336(3) Uani 1 1 d . . . C32 C 0.0847(2) -0.1604(2) 0.35354(15) 0.0316(4) Uani 1 1 d . . . H32A H 0.1630 -0.2571 0.3091 0.047 Uiso 1 1 calc R . . H32B H -0.0285 -0.1019 0.3256 0.047 Uiso 1 1 calc R . . H32C H 0.0646 -0.2048 0.4254 0.047 Uiso 1 1 calc R . . C4 C 0.1223(2) 0.0696(2) 0.16797(13) 0.0248(3) Uani 1 1 d . . . H4 H 0.0754 -0.0168 0.1743 0.030 Uiso 1 1 calc R . . C5 C 0.0978(3) 0.1741(2) 0.06317(14) 0.0310(4) Uani 1 1 d . . . H5A H -0.0282 0.2553 0.0681 0.037 Uiso 1 1 calc R . . H5B H 0.1168 0.0911 0.0086 0.037 Uiso 1 1 calc R . . C6 C 0.2078(2) 0.2818(2) 0.01992(14) 0.0295(4) Uani 1 1 d . . . H6A H 0.1404 0.3741 -0.0290 0.035 Uiso 1 1 calc R . . H6B H 0.3185 0.2050 -0.0213 0.035 Uiso 1 1 calc R . . C7 C 0.2569(2) 0.3679(2) 0.10400(13) 0.0268(4) Uani 1 1 d . . . H7 H 0.3117 0.4485 0.0690 0.032 Uiso 1 1 calc R . . C8 C 0.1017(2) 0.4648(2) 0.19186(14) 0.0306(4) Uani 1 1 d . . . H8A H 0.0778 0.5900 0.1893 0.037 Uiso 1 1 calc R . . H8B H -0.0079 0.4520 0.1823 0.037 Uiso 1 1 calc R . . C9 C 0.1657(2) 0.3771(2) 0.29901(13) 0.0250(3) Uani 1 1 d . . . H9A H 0.2265 0.4382 0.3286 0.030 Uiso 1 1 calc R . . H9B H 0.0655 0.3747 0.3510 0.030 Uiso 1 1 calc R . . C11 C 0.6112(2) 0.3572(2) 0.23185(12) 0.0203(3) Uani 1 1 d . . . C12 C 0.5701(2) 0.5314(2) 0.19214(13) 0.0225(3) Uani 1 1 d . . . H12 H 0.5324 0.5661 0.1247 0.027 Uiso 1 1 calc R . . C13 C 0.5862(2) 0.6520(2) 0.25460(13) 0.0237(3) Uani 1 1 d . . . H13 H 0.5601 0.7676 0.2280 0.028 Uiso 1 1 calc R . . C14 C 0.6405(2) 0.6034(2) 0.35633(13) 0.0234(3) Uani 1 1 d . . . C15 C 0.6757(2) 0.4300(2) 0.39508(13) 0.0260(3) Uani 1 1 d . . . H15 H 0.7085 0.3965 0.4637 0.031 Uiso 1 1 calc R . . C16 C 0.6630(2) 0.3063(2) 0.33380(13) 0.0242(3) Uani 1 1 d . . . H16 H 0.6889 0.1907 0.3605 0.029 Uiso 1 1 calc R . . C17 C 0.6623(3) 0.7341(2) 0.42259(15) 0.0316(4) Uani 1 1 d . . . H17A H 0.5559 0.7844 0.4733 0.047 Uiso 1 1 calc R . . H17B H 0.6797 0.8267 0.3763 0.047 Uiso 1 1 calc R . . H17C H 0.7652 0.6742 0.4603 0.047 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 0.0203(2) 0.0237(2) 0.0235(2) 0.00011(14) -0.00303(15) -0.01210(15) O1 0.0228(6) 0.0237(6) 0.0366(7) -0.0002(5) -0.0064(5) -0.0093(5) O2 0.0325(7) 0.0367(7) 0.0232(6) -0.0019(5) 0.0005(5) -0.0202(5) N1 0.0202(7) 0.0256(6) 0.0224(7) 0.0041(5) -0.0071(5) -0.0124(5) C2 0.0201(7) 0.0240(7) 0.0209(8) 0.0004(6) -0.0048(6) -0.0118(6) C3 0.0169(7) 0.0198(7) 0.0259(8) -0.0019(6) -0.0020(6) -0.0083(6) C31 0.0203(8) 0.0222(7) 0.0290(9) 0.0007(6) -0.0028(6) -0.0086(6) O31 0.0394(7) 0.0420(7) 0.0272(7) 0.0045(5) -0.0077(5) -0.0244(6) C32 0.0331(10) 0.0284(8) 0.0386(10) 0.0059(7) -0.0071(8) -0.0184(7) C4 0.0227(8) 0.0265(8) 0.0292(9) -0.0032(6) -0.0027(7) -0.0137(6) C5 0.0330(10) 0.0392(9) 0.0261(9) -0.0019(7) -0.0082(7) -0.0179(8) C6 0.0302(9) 0.0351(9) 0.0259(9) 0.0035(7) -0.0106(7) -0.0142(7) C7 0.0285(9) 0.0279(8) 0.0274(9) 0.0077(6) -0.0125(7) -0.0135(7) C8 0.0319(9) 0.0238(8) 0.0348(10) -0.0026(7) -0.0137(8) -0.0060(7) C9 0.0267(8) 0.0233(7) 0.0277(9) -0.0033(6) -0.0064(7) -0.0111(7) C11 0.0172(7) 0.0243(7) 0.0224(8) 0.0011(6) -0.0028(6) -0.0118(6) C12 0.0218(8) 0.0275(8) 0.0207(8) 0.0043(6) -0.0049(6) -0.0127(6) C13 0.0239(8) 0.0233(7) 0.0260(8) 0.0032(6) -0.0037(6) -0.0124(6) C14 0.0192(8) 0.0302(8) 0.0244(8) -0.0022(6) -0.0018(6) -0.0135(6) C15 0.0258(8) 0.0343(9) 0.0219(8) 0.0038(6) -0.0079(7) -0.0153(7) C16 0.0228(8) 0.0256(8) 0.0257(8) 0.0048(6) -0.0057(6) -0.0115(6) C17 0.0360(10) 0.0370(9) 0.0298(9) -0.0024(7) -0.0073(7) -0.0214(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 O2 1.4333(12) . ? S1 O1 1.4333(12) . ? S1 N1 1.6176(13) . ? S1 C11 1.7685(15) . ? N1 C2 1.468(2) . ? N1 C7 1.490(2) . ? C2 C3 1.5191(19) . ? C2 C9 1.534(2) . ? C2 H2 0.9800 . ? C3 C4 1.345(2) . ? C3 C31 1.489(2) . ? C31 O31 1.226(2) . ? C31 C32 1.504(2) . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C4 C5 1.502(2) . ? C4 H4 0.9300 . ? C5 C6 1.515(2) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.520(2) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.544(3) . ? C7 H7 0.9800 . ? C8 C9 1.534(2) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C11 C16 1.391(2) . ? C11 C12 1.398(2) . ? C12 C13 1.388(2) . ? C12 H12 0.9300 . ? C13 C14 1.394(2) . ? C13 H13 0.9300 . ? C14 C15 1.395(2) . ? C14 C17 1.510(2) . ? C15 C16 1.386(2) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S1 O1 119.92(7) . . ? O2 S1 N1 106.13(7) . . ? O1 S1 N1 106.81(7) . . ? O2 S1 C11 107.49(7) . . ? O1 S1 C11 106.87(7) . . ? N1 S1 C11 109.33(7) . . ? C2 N1 C7 108.33(12) . . ? C2 N1 S1 120.77(10) . . ? C7 N1 S1 120.04(10) . . ? N1 C2 C3 110.29(12) . . ? N1 C2 C9 102.66(12) . . ? C3 C2 C9 111.60(13) . . ? N1 C2 H2 110.7 . . ? C3 C2 H2 110.7 . . ? C9 C2 H2 110.7 . . ? C4 C3 C31 119.90(14) . . ? C4 C3 C2 126.35(14) . . ? C31 C3 C2 113.53(13) . . ? O31 C31 C3 119.88(14) . . ? O31 C31 C32 119.90(15) . . ? C3 C31 C32 120.22(14) . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C3 C4 C5 134.13(15) . . ? C3 C4 H4 112.9 . . ? C5 C4 H4 112.9 . . ? C4 C5 C6 122.39(14) . . ? C4 C5 H5A 106.7 . . ? C6 C5 H5A 106.7 . . ? C4 C5 H5B 106.7 . . ? C6 C5 H5B 106.7 . . ? H5A C5 H5B 106.6 . . ? C5 C6 C7 115.46(15) . . ? C5 C6 H6A 108.4 . . ? C7 C6 H6A 108.4 . . ? C5 C6 H6B 108.4 . . ? C7 C6 H6B 108.4 . . ? H6A C6 H6B 107.5 . . ? N1 C7 C6 106.33(13) . . ? N1 C7 C8 104.59(13) . . ? C6 C7 C8 115.76(14) . . ? N1 C7 H7 110.0 . . ? C6 C7 H7 110.0 . . ? C8 C7 H7 110.0 . . ? C9 C8 C7 105.88(13) . . ? C9 C8 H8A 110.6 . . ? C7 C8 H8A 110.6 . . ? C9 C8 H8B 110.6 . . ? C7 C8 H8B 110.6 . . ? H8A C8 H8B 108.7 . . ? C2 C9 C8 102.62(13) . . ? C2 C9 H9A 111.2 . . ? C8 C9 H9A 111.2 . . ? C2 C9 H9B 111.2 . . ? C8 C9 H9B 111.2 . . ? H9A C9 H9B 109.2 . . ? C16 C11 C12 120.51(14) . . ? C16 C11 S1 119.96(12) . . ? C12 C11 S1 119.52(12) . . ? C13 C12 C11 119.13(14) . . ? C13 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? C12 C13 C14 121.40(14) . . ? C12 C13 H13 119.3 . . ? C14 C13 H13 119.3 . . ? C13 C14 C15 118.20(14) . . ? C13 C14 C17 121.05(14) . . ? C15 C14 C17 120.75(15) . . ? C16 C15 C14 121.57(15) . . ? C16 C15 H15 119.2 . . ? C14 C15 H15 119.2 . . ? C15 C16 C11 119.16(15) . . ? C15 C16 H16 120.4 . . ? C11 C16 H16 120.4 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 S1 N1 C2 -177.78(11) . . . . ? O1 S1 N1 C2 53.18(13) . . . . ? C11 S1 N1 C2 -62.12(13) . . . . ? O2 S1 N1 C7 -37.68(14) . . . . ? O1 S1 N1 C7 -166.72(12) . . . . ? C11 S1 N1 C7 77.98(13) . . . . ? C7 N1 C2 C3 81.85(14) . . . . ? S1 N1 C2 C3 -133.96(12) . . . . ? C7 N1 C2 C9 -37.19(14) . . . . ? S1 N1 C2 C9 107.01(12) . . . . ? N1 C2 C3 C4 -31.8(2) . . . . ? C9 C2 C3 C4 81.7(2) . . . . ? N1 C2 C3 C31 153.73(13) . . . . ? C9 C2 C3 C31 -92.83(16) . . . . ? C4 C3 C31 O31 -171.72(16) . . . . ? C2 C3 C31 O31 3.2(2) . . . . ? C4 C3 C31 C32 8.8(2) . . . . ? C2 C3 C31 C32 -176.33(14) . . . . ? C31 C3 C4 C5 169.65(18) . . . . ? C2 C3 C4 C5 -4.5(3) . . . . ? C3 C4 C5 C6 18.6(3) . . . . ? C4 C5 C6 C7 -34.4(2) . . . . ? C2 N1 C7 C6 -103.27(14) . . . . ? S1 N1 C7 C6 112.23(13) . . . . ? C2 N1 C7 C8 19.70(15) . . . . ? S1 N1 C7 C8 -124.80(12) . . . . ? C5 C6 C7 N1 69.38(18) . . . . ? C5 C6 C7 C8 -46.3(2) . . . . ? N1 C7 C8 C9 5.75(16) . . . . ? C6 C7 C8 C9 122.38(15) . . . . ? N1 C2 C9 C8 39.11(15) . . . . ? C3 C2 C9 C8 -79.00(16) . . . . ? C7 C8 C9 C2 -27.44(16) . . . . ? O2 S1 C11 C16 -148.00(13) . . . . ? O1 S1 C11 C16 -18.05(15) . . . . ? N1 S1 C11 C16 97.21(14) . . . . ? O2 S1 C11 C12 31.87(15) . . . . ? O1 S1 C11 C12 161.82(12) . . . . ? N1 S1 C11 C12 -82.92(14) . . . . ? C16 C11 C12 C13 1.7(2) . . . . ? S1 C11 C12 C13 -178.21(12) . . . . ? C11 C12 C13 C14 -0.7(2) . . . . ? C12 C13 C14 C15 -1.1(2) . . . . ? C12 C13 C14 C17 178.40(15) . . . . ? C13 C14 C15 C16 2.0(2) . . . . ? C17 C14 C15 C16 -177.53(15) . . . . ? C14 C15 C16 C11 -1.0(2) . . . . ? C12 C11 C16 C15 -0.8(2) . . . . ? S1 C11 C16 C15 179.05(12) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.507 _refine_diff_density_min -0.410 _refine_diff_density_rms 0.054 #===END data_stephenr5 _database_code_depnum_ccdc_archive 'CCDC 681987' _audit_creation_method 'SHELXL-97 and CrysAlis RED' _chemical_name_systematic ; ? ; _chemical_name_common 'Compound 15' _chemical_melting_point ? _chemical_formula_structural p-tolyl-SO2-NC8H11-CO-Et _chemical_formula_moiety 'C18 H23 N O3 S' _chemical_formula_sum 'C18 H23 N O3 S' _chemical_formula_weight 333.43 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.1977(5) _cell_length_b 17.9533(11) _cell_length_c 11.3881(8) _cell_angle_alpha 90.00 _cell_angle_beta 97.878(5) _cell_angle_gamma 90.00 _cell_volume 1660.23(18) _cell_formula_units_Z 4 _cell_measurement_temperature 140(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.33 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.210 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.962 _exptl_absorpt_correction_T_max 1.035 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28c4 beta Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 140(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type Mo-K\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur 3/CCD' _diffrn_measurement_method 'Thin slice \f and \w scans' _diffrn_detector_area_resol_mean 16.0050 _diffrn_reflns_number 21735 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_sigmaI/netI 0.0170 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.48 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3810 _reflns_number_gt 3310 _reflns_threshold_expression I>2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.28c4 beta ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28c4 beta ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28c4 beta ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997a)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997b)' _computing_molecular_graphics 'ORTEP (Johnson, 1971)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997b)' _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^)+(0.0436P)^2^+0.5748P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3810 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0381 _refine_ls_R_factor_gt 0.0317 _refine_ls_wR_factor_ref 0.0855 _refine_ls_wR_factor_gt 0.0829 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 0.47974(4) 0.219878(17) 0.74248(3) 0.01835(9) Uani 1 1 d . . . O1 O 0.34277(11) 0.17229(5) 0.70259(9) 0.0249(2) Uani 1 1 d . . . O2 O 0.54841(12) 0.22022(5) 0.86545(8) 0.0256(2) Uani 1 1 d . . . N1 N 0.62888(12) 0.19604(6) 0.66842(9) 0.0171(2) Uani 1 1 d . . . C2 C 0.59134(15) 0.19546(7) 0.53715(10) 0.0186(2) Uani 1 1 d . . . H2 H 0.4722 0.2004 0.5140 0.022 Uiso 1 1 calc R . . C3 C 0.64999(15) 0.12352(7) 0.48721(10) 0.0193(2) Uani 1 1 d . . . C4 C 0.80446(15) 0.09777(7) 0.51083(11) 0.0225(3) Uani 1 1 d . . . H4 H 0.8246 0.0518 0.4779 0.027 Uiso 1 1 calc R . . C5 C 0.94930(16) 0.13438(8) 0.58434(12) 0.0263(3) Uani 1 1 d . . . H5A H 0.9900 0.1729 0.5362 0.032 Uiso 1 1 calc R . . H5B H 1.0357 0.0973 0.5999 0.032 Uiso 1 1 calc R . . C6 C 0.92451(15) 0.16948(8) 0.70300(12) 0.0245(3) Uani 1 1 d . . . H6A H 0.8958 0.1302 0.7549 0.029 Uiso 1 1 calc R . . H6B H 1.0290 0.1902 0.7387 0.029 Uiso 1 1 calc R . . C7 C 0.79425(15) 0.23048(7) 0.69938(11) 0.0208(2) Uani 1 1 d . . . H7 H 0.8014 0.2547 0.7771 0.025 Uiso 1 1 calc R . . C8 C 0.80414(17) 0.28961(7) 0.60261(13) 0.0265(3) Uani 1 1 d . . . H8A H 0.7764 0.3385 0.6305 0.032 Uiso 1 1 calc R . . H8B H 0.9143 0.2915 0.5806 0.032 Uiso 1 1 calc R . . C9 C 0.67873(17) 0.26544(7) 0.49622(12) 0.0263(3) Uani 1 1 d . . . H9A H 0.7343 0.2538 0.4286 0.032 Uiso 1 1 calc R . . H9B H 0.5996 0.3049 0.4740 0.032 Uiso 1 1 calc R . . C11 C 0.42096(15) 0.31191(7) 0.70087(11) 0.0188(2) Uani 1 1 d . . . C12 C 0.50846(15) 0.37149(7) 0.75666(11) 0.0221(3) Uani 1 1 d . . . H12 H 0.5910 0.3633 0.8200 0.026 Uiso 1 1 calc R . . C13 C 0.47075(16) 0.44313(7) 0.71642(12) 0.0251(3) Uani 1 1 d . . . H13 H 0.5291 0.4831 0.7533 0.030 Uiso 1 1 calc R . . C14 C 0.34713(17) 0.45664(7) 0.62169(12) 0.0252(3) Uani 1 1 d . . . C15 C 0.26073(17) 0.39603(7) 0.56800(12) 0.0260(3) Uani 1 1 d . . . H15 H 0.1775 0.4041 0.5051 0.031 Uiso 1 1 calc R . . C16 C 0.29669(15) 0.32373(7) 0.60678(11) 0.0227(3) Uani 1 1 d . . . H16 H 0.2383 0.2837 0.5702 0.027 Uiso 1 1 calc R . . C17 C 0.3091(2) 0.53512(8) 0.57954(14) 0.0359(3) Uani 1 1 d . . . H17A H 0.3971 0.5534 0.5399 0.054 Uiso 1 1 calc R . . H17B H 0.2977 0.5664 0.6463 0.054 Uiso 1 1 calc R . . H17C H 0.2082 0.5355 0.5256 0.054 Uiso 1 1 calc R . . C31 C 0.52452(16) 0.08474(7) 0.40060(11) 0.0223(3) Uani 1 1 d . . . O31 O 0.38556(13) 0.10966(6) 0.38063(11) 0.0421(3) Uani 1 1 d . . . C32 C 0.57062(17) 0.01566(7) 0.33613(12) 0.0248(3) Uani 1 1 d . . . H32A H 0.6726 0.0249 0.3043 0.030 Uiso 1 1 calc R . . H32B H 0.5895 -0.0251 0.3922 0.030 Uiso 1 1 calc R . . C33 C 0.4389(2) -0.00697(8) 0.23594(13) 0.0343(3) Uani 1 1 d . . . H33A H 0.4736 -0.0509 0.1982 0.051 Uiso 1 1 calc R . . H33B H 0.4216 0.0327 0.1790 0.051 Uiso 1 1 calc R . . H33C H 0.3381 -0.0170 0.2670 0.051 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 0.01601(15) 0.02118(16) 0.01839(15) 0.00179(11) 0.00424(11) 0.00148(11) O1 0.0178(4) 0.0236(5) 0.0341(5) 0.0014(4) 0.0068(4) -0.0024(3) O2 0.0265(5) 0.0335(5) 0.0174(4) 0.0036(4) 0.0048(4) 0.0064(4) N1 0.0146(5) 0.0205(5) 0.0163(5) -0.0004(4) 0.0027(4) 0.0004(4) C2 0.0185(6) 0.0212(6) 0.0159(6) 0.0004(4) 0.0014(4) 0.0023(4) C3 0.0198(6) 0.0216(6) 0.0165(5) 0.0000(4) 0.0025(4) 0.0001(5) C4 0.0215(6) 0.0243(6) 0.0217(6) -0.0024(5) 0.0031(5) 0.0025(5) C5 0.0169(6) 0.0322(7) 0.0294(7) -0.0055(5) 0.0016(5) 0.0036(5) C6 0.0158(6) 0.0325(7) 0.0244(6) -0.0030(5) -0.0005(5) 0.0009(5) C7 0.0154(6) 0.0257(6) 0.0211(6) -0.0043(5) 0.0022(4) -0.0030(5) C8 0.0241(6) 0.0232(6) 0.0337(7) -0.0005(5) 0.0095(5) -0.0038(5) C9 0.0330(7) 0.0241(6) 0.0230(6) 0.0039(5) 0.0082(5) 0.0003(5) C11 0.0167(6) 0.0206(6) 0.0195(6) -0.0001(5) 0.0040(4) 0.0021(4) C12 0.0182(6) 0.0273(6) 0.0203(6) -0.0040(5) 0.0012(5) 0.0013(5) C13 0.0246(6) 0.0235(6) 0.0277(7) -0.0060(5) 0.0052(5) -0.0027(5) C14 0.0297(7) 0.0229(6) 0.0241(6) 0.0003(5) 0.0077(5) 0.0022(5) C15 0.0266(7) 0.0272(7) 0.0226(6) 0.0003(5) -0.0025(5) 0.0044(5) C16 0.0200(6) 0.0234(6) 0.0237(6) -0.0034(5) -0.0008(5) 0.0001(5) C17 0.0489(9) 0.0240(7) 0.0349(8) 0.0040(6) 0.0065(7) 0.0034(6) C31 0.0226(6) 0.0240(6) 0.0194(6) 0.0005(5) 0.0000(5) 0.0006(5) O31 0.0265(5) 0.0456(6) 0.0492(7) -0.0202(5) -0.0132(5) 0.0110(5) C32 0.0271(7) 0.0236(6) 0.0235(6) -0.0020(5) 0.0023(5) -0.0003(5) C33 0.0413(9) 0.0264(7) 0.0317(8) -0.0065(6) -0.0076(6) 0.0010(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.4343(9) . ? S1 O2 1.4360(9) . ? S1 N1 1.6345(10) . ? S1 C11 1.7676(12) . ? N1 C2 1.4844(15) . ? N1 C7 1.4878(15) . ? C2 C3 1.5158(16) . ? C2 C9 1.5493(17) . ? C2 H2 0.9800 . ? C3 C4 1.3403(17) . ? C3 C31 1.4958(17) . ? C4 C5 1.5066(18) . ? C4 H4 0.9300 . ? C5 C6 1.5297(18) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.5262(17) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.5403(18) . ? C7 H7 0.9800 . ? C8 C9 1.5401(19) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C11 C16 1.3899(17) . ? C11 C12 1.3918(17) . ? C12 C13 1.3859(19) . ? C12 H12 0.9300 . ? C13 C14 1.3964(19) . ? C13 H13 0.9300 . ? C14 C15 1.3931(19) . ? C14 C17 1.5074(19) . ? C15 C16 1.3896(18) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C31 O31 1.2160(16) . ? C31 C32 1.5153(18) . ? C32 C33 1.5149(18) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 O2 119.78(6) . . ? O1 S1 N1 106.80(5) . . ? O2 S1 N1 106.46(5) . . ? O1 S1 C11 107.40(6) . . ? O2 S1 C11 108.27(6) . . ? N1 S1 C11 107.59(5) . . ? C2 N1 C7 107.33(9) . . ? C2 N1 S1 117.06(8) . . ? C7 N1 S1 119.38(8) . . ? N1 C2 C3 110.56(9) . . ? N1 C2 C9 104.88(10) . . ? C3 C2 C9 113.24(10) . . ? N1 C2 H2 109.3 . . ? C3 C2 H2 109.3 . . ? C9 C2 H2 109.3 . . ? C4 C3 C31 121.14(11) . . ? C4 C3 C2 123.93(11) . . ? C31 C3 C2 114.79(10) . . ? C3 C4 C5 127.74(12) . . ? C3 C4 H4 116.1 . . ? C5 C4 H4 116.1 . . ? C4 C5 C6 118.72(11) . . ? C4 C5 H5A 107.6 . . ? C6 C5 H5A 107.6 . . ? C4 C5 H5B 107.6 . . ? C6 C5 H5B 107.6 . . ? H5A C5 H5B 107.1 . . ? C7 C6 C5 116.68(11) . . ? C7 C6 H6A 108.1 . . ? C5 C6 H6A 108.1 . . ? C7 C6 H6B 108.1 . . ? C5 C6 H6B 108.1 . . ? H6A C6 H6B 107.3 . . ? N1 C7 C6 108.65(10) . . ? N1 C7 C8 104.63(10) . . ? C6 C7 C8 114.12(11) . . ? N1 C7 H7 109.8 . . ? C6 C7 H7 109.8 . . ? C8 C7 H7 109.8 . . ? C9 C8 C7 105.88(10) . . ? C9 C8 H8A 110.6 . . ? C7 C8 H8A 110.6 . . ? C9 C8 H8B 110.6 . . ? C7 C8 H8B 110.6 . . ? H8A C8 H8B 108.7 . . ? C8 C9 C2 106.15(10) . . ? C8 C9 H9A 110.5 . . ? C2 C9 H9A 110.5 . . ? C8 C9 H9B 110.5 . . ? C2 C9 H9B 110.5 . . ? H9A C9 H9B 108.7 . . ? C16 C11 C12 120.80(12) . . ? C16 C11 S1 119.57(9) . . ? C12 C11 S1 119.44(9) . . ? C13 C12 C11 118.99(12) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? C12 C13 C14 121.46(12) . . ? C12 C13 H13 119.3 . . ? C14 C13 H13 119.3 . . ? C15 C14 C13 118.35(12) . . ? C15 C14 C17 121.32(13) . . ? C13 C14 C17 120.33(13) . . ? C16 C15 C14 121.14(12) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C15 C16 C11 119.26(12) . . ? C15 C16 H16 120.4 . . ? C11 C16 H16 120.4 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O31 C31 C3 119.60(12) . . ? O31 C31 C32 120.00(12) . . ? C3 C31 C32 120.39(11) . . ? C33 C32 C31 112.65(11) . . ? C33 C32 H32A 109.1 . . ? C31 C32 H32A 109.1 . . ? C33 C32 H32B 109.1 . . ? C31 C32 H32B 109.1 . . ? H32A C32 H32B 107.8 . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 S1 N1 C2 54.10(10) . . . . ? O2 S1 N1 C2 -176.84(8) . . . . ? C11 S1 N1 C2 -60.95(10) . . . . ? O1 S1 N1 C7 -173.70(9) . . . . ? O2 S1 N1 C7 -44.64(10) . . . . ? C11 S1 N1 C7 71.24(10) . . . . ? C7 N1 C2 C3 90.82(11) . . . . ? S1 N1 C2 C3 -131.73(9) . . . . ? C7 N1 C2 C9 -31.57(12) . . . . ? S1 N1 C2 C9 105.88(10) . . . . ? N1 C2 C3 C4 -54.11(16) . . . . ? C9 C2 C3 C4 63.24(16) . . . . ? N1 C2 C3 C31 130.23(11) . . . . ? C9 C2 C3 C31 -112.43(12) . . . . ? C31 C3 C4 C5 172.58(12) . . . . ? C2 C3 C4 C5 -2.8(2) . . . . ? C3 C4 C5 C6 44.4(2) . . . . ? C4 C5 C6 C7 -58.19(17) . . . . ? C2 N1 C7 C6 -88.39(11) . . . . ? S1 N1 C7 C6 135.33(9) . . . . ? C2 N1 C7 C8 33.87(12) . . . . ? S1 N1 C7 C8 -102.41(10) . . . . ? C5 C6 C7 N1 69.46(14) . . . . ? C5 C6 C7 C8 -46.84(15) . . . . ? N1 C7 C8 C9 -22.31(13) . . . . ? C6 C7 C8 C9 96.30(12) . . . . ? C7 C8 C9 C2 3.51(14) . . . . ? N1 C2 C9 C8 16.62(13) . . . . ? C3 C2 C9 C8 -104.01(12) . . . . ? O1 S1 C11 C16 -23.68(12) . . . . ? O2 S1 C11 C16 -154.34(10) . . . . ? N1 S1 C11 C16 90.98(11) . . . . ? O1 S1 C11 C12 161.36(10) . . . . ? O2 S1 C11 C12 30.70(12) . . . . ? N1 S1 C11 C12 -83.99(11) . . . . ? C16 C11 C12 C13 -0.48(19) . . . . ? S1 C11 C12 C13 174.43(10) . . . . ? C11 C12 C13 C14 0.13(19) . . . . ? C12 C13 C14 C15 0.3(2) . . . . ? C12 C13 C14 C17 -179.81(13) . . . . ? C13 C14 C15 C16 -0.4(2) . . . . ? C17 C14 C15 C16 179.71(13) . . . . ? C14 C15 C16 C11 0.1(2) . . . . ? C12 C11 C16 C15 0.38(19) . . . . ? S1 C11 C16 C15 -174.52(10) . . . . ? C4 C3 C31 O31 -179.66(13) . . . . ? C2 C3 C31 O31 -3.86(18) . . . . ? C4 C3 C31 C32 -0.86(19) . . . . ? C2 C3 C31 C32 174.94(11) . . . . ? O31 C31 C32 C33 9.84(19) . . . . ? C3 C31 C32 C33 -168.96(12) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.350 _refine_diff_density_min -0.379 _refine_diff_density_rms 0.041