data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'E. Thomas' 'Alison M. Baylis' 'Michael. P. H. Davies' _publ_contact_author_address ; Department of Chemistry University of Manchester MANCHESTER M13 9PL UNITED KINGDOM ; _publ_contact_author_email E.J.THOMAS@MAN.AC.UK _publ_contact_author_name 'E. Thomas' _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Synthetic approaches to the polycyclic alkaloid stemofoline ; data_S108/EJT/MD _database_code_depnum_ccdc_archive 'CCDC 650400' #------------------------------------------------------------------------------ _audit_creation_date 19106-11-21 _audit_creation_method 'by teXsan v1.7' _audit_update_record ; ? ; _publ_section_references ; Molecular Structure Corporation. (1995). teXsan. Single Crystal Structure Analysis Software. Version 1.7. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Walker, N. & Stuart. D. (1983). Acta Cryst. A39, 158-166. ; #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1995)' _computing_structure_solution ? _computing_structure_refinement 'teXsan (MSC, 1995)' _computing_publication_material 'teXsan (MSC, 1995)' #------------------------------------------------------------------------------ _cell_length_a 10.716(1) _cell_length_b 20.066(2) _cell_length_c 10.835(1) _cell_angle_alpha 90 _cell_angle_beta 91.767(9) _cell_angle_gamma 90 _cell_volume 2328.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296.2 _cell_measurement_reflns_used 20 _cell_measurement_theta_min 31.8 _cell_measurement_theta_max 37.9 #------------------------------------------------------------------------------ _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x,1/2+y,1/2-z' ' -x, -y, -z' ' +x,1/2-y,1/2+z' #------------------------------------------------------------------------------ _exptl_crystal_description acicular _exptl_crystal_colour colourlessacicular _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.01 _exptl_crystal_density_diffrn 1.417 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 496.83 _chemical_formula_analytical ? _chemical_formula_sum 'C20 H24 Cl3 N O5 S ' _chemical_formula_moiety 'C20 H24 Cl3 N O5 S ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 1032.00 _exptl_absorpt_coefficient_mu 4.730 _exptl_absorpt_correction_type ; \DF (DIFABS; Walker & Stuart, 1983) ; _exptl_absorpt_correction_T_max 1.217 _exptl_absorpt_correction_T_min 0.736 _exptl_special_details ; The scan width was (1.21+0.30tan\q)\% with an \w scan speed of 16\% per minute (up to 4 scans to achieve I/\s(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. ; #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 296.2 _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku AFC5R' _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% -13.00 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? ? ? ? ? ? ? _diffrn_reflns_number 2963 _reflns_number_total 2804 _reflns_number_observed 1853 _reflns_observed_criterion >3.00\s(I) _diffrn_reflns_av_R_equivalents 0.04634 _diffrn_reflns_av_sigmaI/netI ? _diffrn_reflns_limit_h_min 100 _diffrn_reflns_limit_h_max -100 _diffrn_reflns_limit_k_min 100 _diffrn_reflns_limit_k_max -100 _diffrn_reflns_limit_l_min 100 _diffrn_reflns_limit_l_max -100 _diffrn_reflns_theta_min 0.00 _diffrn_reflns_theta_max 60.12 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.00321 _diffrn_orient_matrix_UB_12 0.04882 _diffrn_orient_matrix_UB_13 0.01832 _diffrn_orient_matrix_UB_21 -0.07872 _diffrn_orient_matrix_UB_22 0.00670 _diffrn_orient_matrix_UB_23 -0.05045 _diffrn_orient_matrix_UB_31 -0.05009 _diffrn_orient_matrix_UB_32 -0.00740 _diffrn_orient_matrix_UB_33 0.07514 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 80 0.018 0.009 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 96 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; Cl 0 12 0.364 0.702 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; N 0 4 0.031 0.018 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O 0 20 0.049 0.032 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; S 0 4 0.333 0.557 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom Cl1 0.0272(3) 0.3023(2) -0.1280(3) 0.148(1) 1.000 . Uani d ? Cl2 0.0847(4) 0.4318(2) -0.0301(4) 0.178(2) 1.000 . Uani d ? Cl3 0.0199(3) 0.3247(3) 0.1289(4) 0.175(2) 1.000 . Uani d ? S1 0.5036(2) 0.24682(9) 0.1889(2) 0.0552(6) 1.000 . Uani d ? O1 0.4138(6) 0.4205(3) -0.0096(6) 0.076(2) 1.000 . Uani d ? O2 0.3884(5) 0.2182(3) 0.2259(5) 0.067(2) 1.000 . Uani d ? O3 0.5108(5) 0.2737(3) 0.0652(5) 0.066(2) 1.000 . Uani d ? O4 0.7725(6) 0.3182(3) 0.3107(6) 0.081(2) 1.000 . Uani d ? O5 0.2909(5) 0.3563(3) 0.1088(5) 0.064(2) 1.000 . Uani d ? N1 0.4549(6) 0.4105(3) 0.1973(6) 0.057(2) 1.000 . Uani d ? C1 0.3909(8) 0.3971(4) 0.0902(9) 0.056(3) 1.000 . Uani d ? C2 0.5756(9) 0.4444(4) 0.1893(8) 0.071(3) 1.000 . Uani d ? C3 0.6778(8) 0.3933(4) 0.1658(8) 0.068(3) 1.000 . Uani d ? C4 0.6785(9) 0.3380(4) 0.2613(8) 0.062(3) 1.000 . Uani d ? C5 0.5522(7) 0.3119(3) 0.2953(7) 0.049(2) 1.000 . Uani d ? C6 0.4603(8) 0.3716(4) 0.3136(7) 0.057(3) 1.000 . Uani d ? C7 0.5286(8) 0.4223(4) 0.4000(8) 0.068(3) 1.000 . Uani d ? C8 0.5890(9) 0.4739(4) 0.3184(10) 0.083(3) 1.000 . Uani d ? C9 0.3355(8) 0.3524(4) 0.3673(8) 0.063(3) 1.000 . Uani d ? C10 0.2441(9) 0.4087(4) 0.3742(9) 0.075(3) 1.000 . Uani d ? C11 0.129(2) 0.3894(6) 0.446(2) 0.132(6) 1.000 . Uani d ? C12 0.161(2) 0.388(1) 0.575(3) 0.23(1) 1.000 . Uani d ? C13 0.2323(8) 0.3268(4) 0.0035(8) 0.072(3) 1.000 . Uani d ? C14 0.096(1) 0.3453(5) -0.0034(10) 0.098(4) 1.000 . Uani d ? C15 0.6224(9) 0.1865(4) 0.2043(8) 0.056(3) 1.000 . Uani d ? C16 0.7217(9) 0.1881(5) 0.1299(9) 0.072(3) 1.000 . Uani d ? C17 0.8092(9) 0.1371(6) 0.140(1) 0.088(4) 1.000 . Uani d ? C18 0.797(1) 0.0881(5) 0.228(1) 0.086(4) 1.000 . Uani d ? C19 0.698(1) 0.0873(4) 0.303(1) 0.087(4) 1.000 . Uani d ? C20 0.6072(8) 0.1367(4) 0.2923(8) 0.068(3) 1.000 . Uani d ? H2 0.5731 0.4781 0.1279 0.085 1.000 . Uiso c ? H31 0.6639 0.3745 0.0862 0.082 1.000 . Uiso c ? H32 0.7566 0.4151 0.1692 0.082 1.000 . Uiso c ? H5 0.5633 0.2912 0.3738 0.058 1.000 . Uiso c ? H71 0.4706 0.4432 0.4521 0.082 1.000 . Uiso c ? H72 0.5907 0.4001 0.4493 0.082 1.000 . Uiso c ? H81 0.6745 0.4799 0.3417 0.100 1.000 . Uiso c ? H82 0.5467 0.5154 0.3228 0.100 1.000 . Uiso c ? H91 0.2991 0.3183 0.3172 0.076 1.000 . Uiso c ? H92 0.3508 0.3358 0.4485 0.076 1.000 . Uiso c ? H101 0.2839 0.4455 0.4138 0.090 1.000 . Uiso c ? H102 0.2181 0.4210 0.2927 0.090 1.000 . Uiso c ? H111 0.0651 0.4212 0.4309 0.158 1.000 . Uiso c ? H112 0.1012 0.3466 0.4203 0.158 1.000 . Uiso c ? H121 0.0893 0.3753 0.6193 0.274 1.000 . Uiso c ? H122 0.2257 0.3564 0.5901 0.274 1.000 . Uiso c ? H123 0.1879 0.4308 0.6010 0.274 1.000 . Uiso c ? H131 0.2715 0.3421 -0.0686 0.087 1.000 . Uiso c ? H132 0.2400 0.2797 0.0089 0.087 1.000 . Uiso c ? H16 0.7313 0.2232 0.0721 0.086 1.000 . Uiso c ? H17 0.8777 0.1361 0.0868 0.105 1.000 . Uiso c ? H18 0.8591 0.0544 0.2355 0.103 1.000 . Uiso c ? H19 0.6908 0.0530 0.3629 0.105 1.000 . Uiso c ? H20 0.5368 0.1365 0.3435 0.081 1.000 . Uiso c ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl1 0.151(3) 0.132(2) 0.157(3) 0.011(2) -0.076(2) -0.020(2) Cl2 0.185(3) 0.088(2) 0.257(5) 0.057(2) -0.084(3) -0.020(2) Cl3 0.095(2) 0.275(5) 0.156(4) -0.034(3) 0.032(2) -0.017(3) S1 0.060(1) 0.058(1) 0.048(1) 0.005(1) 0.008(1) -0.008(1) O1 0.101(5) 0.079(4) 0.049(4) -0.004(3) 0.011(4) 0.016(3) O2 0.052(3) 0.069(3) 0.079(4) -0.010(3) 0.019(3) -0.009(3) O3 0.082(4) 0.075(3) 0.040(4) 0.007(3) 0.002(3) -0.002(3) O4 0.066(4) 0.096(4) 0.082(5) -0.002(3) -0.003(4) 0.005(3) O5 0.064(4) 0.070(3) 0.058(4) 0.003(3) 0.009(3) -0.003(3) N1 0.070(5) 0.054(4) 0.047(5) 0.001(3) 0.011(4) -0.001(3) C1 0.074(6) 0.052(5) 0.045(6) 0.014(5) 0.019(5) -0.004(4) C2 0.083(6) 0.062(5) 0.068(7) -0.014(5) 0.000(5) 0.007(5) C3 0.057(5) 0.085(6) 0.064(6) -0.009(5) 0.021(5) 0.008(5) C4 0.063(6) 0.070(5) 0.054(6) -0.001(5) 0.002(5) -0.004(4) C5 0.058(5) 0.058(4) 0.030(5) 0.011(4) 0.014(4) -0.005(4) C6 0.079(6) 0.052(4) 0.039(5) 0.003(4) 0.007(5) -0.002(4) C7 0.093(6) 0.058(5) 0.055(6) 0.009(5) 0.010(5) -0.011(4) C8 0.099(7) 0.051(5) 0.099(8) -0.014(5) -0.002(6) -0.003(5) C9 0.077(6) 0.054(4) 0.060(6) 0.016(5) 0.029(5) 0.002(4) C10 0.080(6) 0.071(6) 0.078(8) 0.009(5) 0.049(6) 0.014(5) C11 0.19(2) 0.096(8) 0.12(1) 0.033(9) 0.04(1) -0.001(8) C12 0.17(2) 0.25(2) 0.27(3) -0.03(2) 0.07(2) -0.05(2) C13 0.072(6) 0.072(5) 0.073(7) 0.008(5) -0.004(5) -0.008(5) C14 0.108(8) 0.085(6) 0.098(8) 0.021(6) -0.022(7) -0.008(6) C15 0.063(6) 0.056(5) 0.049(6) 0.002(4) 0.009(5) -0.011(4) C16 0.054(6) 0.091(6) 0.071(7) 0.004(5) 0.015(6) -0.014(5) C17 0.058(6) 0.128(9) 0.077(8) 0.015(7) 0.021(6) -0.034(7) C18 0.087(8) 0.079(7) 0.092(9) 0.025(6) -0.013(7) -0.017(6) C19 0.117(9) 0.063(6) 0.083(8) 0.013(6) 0.011(7) 0.002(5) C20 0.074(6) 0.061(5) 0.069(7) 0.010(5) 0.020(5) -0.011(5) #------------------------------------------------------------------------------ _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme 'w = 1/[\s^2^(Fo) + 0.00022|Fo|^2^]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1853 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all ? _refine_ls_R_factor_obs 0.0774 _refine_ls_wR_factor_all ? _refine_ls_wR_factor_obs 0.0956 _refine_ls_goodness_of_fit_all ? _refine_ls_goodness_of_fit_obs 3.081 _refine_ls_shift/esd_max 0.0415 _refine_ls_shift/esd_mean 0.0000 _refine_diff_density_min -0.36 _refine_diff_density_max 0.75 #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag CL1 C14 1.75(1) . . yes CL2 C14 1.76(1) . . yes CL3 C14 1.72(1) . . yes S1 O2 1.431(5) . . yes S1 O3 1.448(5) . . yes S1 C5 1.807(7) . . yes S1 C15 1.760(9) . . yes O1 C1 1.21(1) . . yes O4 C4 1.19(1) . . yes O5 C1 1.37(1) . . yes O5 C13 1.41(1) . . yes N1 C1 1.36(1) . . yes N1 C2 1.47(1) . . yes N1 C6 1.482(10) . . yes C2 C3 1.53(1) . . yes C2 C8 1.52(1) . . yes C2 H2 0.95 . . no C3 C4 1.52(1) . . yes C3 H31 0.95 . . no C3 H32 0.95 . . no C4 C5 1.51(1) . . yes C5 C6 1.57(1) . . yes C5 H5 0.95 . . no C6 C7 1.55(1) . . yes C6 C9 1.52(1) . . yes C7 C8 1.52(1) . . yes C7 H71 0.95 . . no C7 H72 0.95 . . no C8 H81 0.95 . . no C8 H82 0.95 . . no C9 C10 1.50(1) . . yes C9 H91 0.95 . . no C9 H92 0.95 . . no C10 C11 1.53(2) . . yes C10 H101 0.95 . . no C10 H102 0.95 . . no C11 C12 1.42(3) . . yes C11 H111 0.95 . . no C11 H112 0.95 . . no C12 H121 0.95 . . no C12 H122 0.95 . . no C12 H123 0.95 . . no C13 C14 1.51(1) . . yes C13 H131 0.95 . . no C13 H132 0.95 . . no C15 C16 1.35(1) . . yes C15 C20 1.39(1) . . yes C16 C17 1.39(1) . . yes C16 H16 0.95 . . no C17 C18 1.37(2) . . yes C17 H17 0.95 . . no C18 C19 1.36(2) . . yes C18 H18 0.95 . . no C19 C20 1.39(1) . . yes C19 H19 0.95 . . no C20 H20 0.95 . . no #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S1 O3 118.6(3) . . . yes O2 S1 C5 110.2(3) . . . yes O2 S1 C15 109.0(4) . . . yes O3 S1 C5 107.4(3) . . . yes O3 S1 C15 106.6(4) . . . yes C5 S1 C15 104.1(4) . . . yes C1 O5 C13 117.5(7) . . . yes C1 N1 C2 117.8(7) . . . yes C1 N1 C6 128.9(6) . . . yes C2 N1 C6 106.4(6) . . . yes O1 C1 O5 123.0(8) . . . yes O1 C1 N1 125.1(8) . . . yes O5 C1 N1 111.8(7) . . . yes N1 C2 C3 109.8(6) . . . yes N1 C2 C8 100.6(7) . . . yes N1 C2 H2 111.5 . . . no C3 C2 C8 111.5(7) . . . yes C3 C2 H2 111.5 . . . no C8 C2 H2 111.5 . . . no C2 C3 C4 111.4(7) . . . yes C2 C3 H31 109.0 . . . no C2 C3 H32 109.0 . . . no C4 C3 H31 109.0 . . . no C4 C3 H32 109.0 . . . no H31 C3 H32 109.5 . . . no O4 C4 C3 122.3(8) . . . yes O4 C4 C5 121.8(7) . . . yes C3 C4 C5 115.8(7) . . . yes S1 C5 C4 109.8(5) . . . yes S1 C5 C6 117.6(5) . . . yes S1 C5 H5 106.4 . . . no C4 C5 C6 109.7(6) . . . yes C4 C5 H5 106.4 . . . no C6 C5 H5 106.4 . . . no N1 C6 C5 107.6(6) . . . yes N1 C6 C7 100.0(6) . . . yes N1 C6 C9 116.5(7) . . . yes C5 C6 C7 106.9(6) . . . yes C5 C6 C9 114.6(6) . . . yes C7 C6 C9 109.8(6) . . . yes C6 C7 C8 107.3(7) . . . yes C6 C7 H71 110.0 . . . no C6 C7 H72 110.0 . . . no C8 C7 H71 110.0 . . . no C8 C7 H72 110.0 . . . no H71 C7 H72 109.5 . . . no C2 C8 C7 103.9(7) . . . yes C2 C8 H81 110.8 . . . no C2 C8 H82 110.8 . . . no C7 C8 H81 110.9 . . . no C7 C8 H82 110.9 . . . no H81 C8 H82 109.5 . . . no C6 C9 C10 114.3(7) . . . yes C6 C9 H91 108.3 . . . no C6 C9 H92 108.3 . . . no C10 C9 H91 108.3 . . . no C10 C9 H92 108.3 . . . no H91 C9 H92 109.5 . . . no C9 C10 C11 111.8(8) . . . yes C9 C10 H101 108.9 . . . no C9 C10 H102 108.9 . . . no C11 C10 H101 108.9 . . . no C11 C10 H102 108.9 . . . no H101 C10 H102 109.4 . . . no C10 C11 C12 109(1) . . . yes C10 C11 H111 109.4 . . . no C10 C11 H112 109.4 . . . no C12 C11 H111 109.4 . . . no C12 C11 H112 109.4 . . . no H111 C11 H112 109.5 . . . no C11 C12 H121 109.4 . . . no C11 C12 H122 109.4 . . . no C11 C12 H123 109.4 . . . no H121 C12 H122 109.6 . . . no H121 C12 H123 109.5 . . . no H122 C12 H123 109.5 . . . no O5 C13 C14 110.0(7) . . . yes O5 C13 H131 109.3 . . . no O5 C13 H132 109.4 . . . no C14 C13 H131 109.3 . . . no C14 C13 H132 109.3 . . . no H131 C13 H132 109.5 . . . no CL1 C14 CL2 109.6(6) . . . yes CL1 C14 CL3 109.0(6) . . . yes CL1 C14 C13 107.6(7) . . . yes CL2 C14 CL3 109.9(6) . . . yes CL2 C14 C13 108.3(7) . . . yes CL3 C14 C13 112.5(7) . . . yes S1 C15 C16 120.4(7) . . . yes S1 C15 C20 117.3(7) . . . yes C16 C15 C20 122.3(8) . . . yes C15 C16 C17 118.3(9) . . . yes C15 C16 H16 120.8 . . . no C17 C16 H16 120.9 . . . no C16 C17 C18 120.4(10) . . . yes C16 C17 H17 119.8 . . . no C18 C17 H17 119.8 . . . no C17 C18 C19 120.9(10) . . . yes C17 C18 H18 119.5 . . . no C19 C18 H18 119.5 . . . no C18 C19 C20 119.9(9) . . . yes C18 C19 H19 120.0 . . . no C20 C19 H19 120.0 . . . no C15 C20 C19 118.1(9) . . . yes C15 C20 H20 120.9 . . . no C19 C20 H20 120.9 . . . no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 C20 3.24(1) . 4_554 no #------------------------------------------------------------------------------ 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 CL1 C14 C13 O5 . . . . -175.5(6) no CL1 C14 C13 H131 . . . . 64.4(9) no CL1 C14 C13 H132 . . . . -55.4(10) no CL2 C14 C13 O5 . . . . 66.2(8) no CL2 C14 C13 H131 . . . . -53.9(9) no CL2 C14 C13 H132 . . . . -173.7(7) no CL3 C14 C13 O5 . . . . -55.5(9) no CL3 C14 C13 H131 . . . . -175.6(7) no CL3 C14 C13 H132 . . . . 64.6(10) no S1 C5 C4 O4 . . . . -96.5(8) no S1 C5 C4 C3 . . . . 86.7(7) no S1 C5 C6 N1 . . . . -68.8(7) no S1 C5 C6 C7 . . . . -175.5(5) no S1 C5 C6 C9 . . . . 62.6(8) no S1 C15 C16 C17 . . . . -176.1(7) no S1 C15 C16 H16 . . . . 3(1) no S1 C15 C20 C19 . . . . 177.9(7) no S1 C15 C20 H20 . . . . -2(1) no O1 C1 O5 C13 . . . . 16(1) no O1 C1 N1 C2 . . . . -13(1) no O1 C1 N1 C6 . . . . -160.1(8) no O2 S1 C5 C4 . . . . 175.5(5) no O2 S1 C5 C6 . . . . -58.1(6) no O2 S1 C5 H5 . . . . 60.9(6) no O2 S1 C15 C16 . . . . 150.9(7) no O2 S1 C15 C20 . . . . -27.0(8) no O3 S1 C5 C4 . . . . -53.9(6) no O3 S1 C5 C6 . . . . 72.5(6) no O3 S1 C5 H5 . . . . -168.5(5) no O3 S1 C15 C16 . . . . 21.7(8) no O3 S1 C15 C20 . . . . -156.1(6) no O4 C4 C3 C2 . . . . -134.6(8) no O4 C4 C3 H31 . . . . 105.1(9) no O4 C4 C3 H32 . . . . -14(1) no O4 C4 C5 C6 . . . . 132.9(8) no O4 C4 C5 H5 . . . . 18(1) no O5 C1 N1 C2 . . . . 170.1(6) no O5 C1 N1 C6 . . . . 23(1) no N1 C1 O5 C13 . . . . -166.7(6) no N1 C2 C3 C4 . . . . -53.8(9) no N1 C2 C3 H31 . . . . 66.5(9) no N1 C2 C3 H32 . . . . -174.1(7) no N1 C2 C8 C7 . . . . 34.5(8) no N1 C2 C8 H81 . . . . 153.6(7) no N1 C2 C8 H82 . . . . -84.7(9) no N1 C6 C5 C4 . . . . 57.6(8) no N1 C6 C5 H5 . . . . 172.2(6) no N1 C6 C7 C8 . . . . -17.0(8) no N1 C6 C7 H71 . . . . 102.7(8) no N1 C6 C7 H72 . . . . -136.6(7) no N1 C6 C9 C10 . . . . -47.9(9) no N1 C6 C9 H91 . . . . 72.8(8) no N1 C6 C9 H92 . . . . -168.6(6) no C1 O5 C13 C14 . . . . -122.6(8) no C1 O5 C13 H131 . . . . -2(1) no C1 O5 C13 H132 . . . . 117.3(8) no C1 N1 C2 C3 . . . . -84.0(8) no C1 N1 C2 C8 . . . . 158.4(7) no C1 N1 C2 H2 . . . . 40(1) no C1 N1 C6 C5 . . . . 78.5(10) no C1 N1 C6 C7 . . . . -170.0(8) no C1 N1 C6 C9 . . . . -51(1) no C2 N1 C6 C5 . . . . -71.0(7) no C2 N1 C6 C7 . . . . 40.5(7) no C2 N1 C6 C9 . . . . 158.7(6) no C2 C3 C4 C5 . . . . 42.2(9) no C2 C8 C7 C6 . . . . -10.7(9) no C2 C8 C7 H71 . . . . -130.3(8) no C2 C8 C7 H72 . . . . 109.0(8) no C3 C2 N1 C6 . . . . 69.5(8) no C3 C2 C8 C7 . . . . -81.9(8) no C3 C2 C8 H81 . . . . 37.2(10) no C3 C2 C8 H82 . . . . 159.0(8) no C3 C4 C5 C6 . . . . -44.0(9) no C3 C4 C5 H5 . . . . -158.6(7) no C4 C3 C2 C8 . . . . 56.8(9) no C4 C3 C2 H2 . . . . -177.9(7) no C4 C5 S1 C15 . . . . 58.9(6) no C4 C5 C6 C7 . . . . -49.1(8) no C4 C5 C6 C9 . . . . -171.0(6) no C5 S1 C15 C16 . . . . -91.6(8) no C5 S1 C15 C20 . . . . 90.5(7) no C5 C4 C3 H31 . . . . -78.1(9) no C5 C4 C3 H32 . . . . 162.5(7) no C5 C6 C7 C8 . . . . 95.1(7) no C5 C6 C7 H71 . . . . -145.3(7) no C5 C6 C7 H72 . . . . -24.6(9) no C5 C6 C9 C10 . . . . -174.9(7) no C5 C6 C9 H91 . . . . -54.2(9) no C5 C6 C9 H92 . . . . 64.4(9) no C6 N1 C2 C8 . . . . -48.1(7) no C6 N1 C2 H2 . . . . -166.5(7) no C6 C5 S1 C15 . . . . -174.8(6) no C6 C7 C8 H81 . . . . -129.8(8) no C6 C7 C8 H82 . . . . 108.4(9) no C6 C9 C10 C11 . . . . -171.3(9) no C6 C9 C10 H101 . . . . -50(1) no C6 C9 C10 H102 . . . . 68.4(10) no C7 C6 C5 H5 . . . . 65.5(8) no C7 C6 C9 C10 . . . . 64.8(9) no C7 C6 C9 H91 . . . . -174.5(7) no C7 C6 C9 H92 . . . . -55.9(8) no C7 C8 C2 H2 . . . . 152.8(8) no C8 C2 C3 H31 . . . . 177.1(7) no C8 C2 C3 H32 . . . . -63.5(10) no C8 C7 C6 C9 . . . . -140.0(7) no C9 C6 C5 H5 . . . . -56.4(9) no C9 C6 C7 H71 . . . . -20.3(9) no C9 C6 C7 H72 . . . . 100.3(8) no C9 C10 C11 C12 . . . . 74(1) no C9 C10 C11 H111 . . . . -165(1) no C9 C10 C11 H112 . . . . -45(1) no C10 C11 C12 H121 . . . . -179(1) no C10 C11 C12 H122 . . . . -59(2) no C10 C11 C12 H123 . . . . 60(1) no C11 C10 C9 H91 . . . . 68(1) no C11 C10 C9 H92 . . . . -50(1) no C12 C11 C10 H101 . . . . -45(1) no C12 C11 C10 H102 . . . . -164(1) no C15 S1 C5 H5 . . . . -55.8(7) no C15 C16 C17 C18 . . . . -2(1) no C15 C16 C17 H17 . . . . 177.3(10) no C15 C20 C19 C18 . . . . 0(1) no C15 C20 C19 H19 . . . . 179.2(9) no C16 C15 C20 C19 . . . . 0(1) no C16 C15 C20 H20 . . . . -179.9(9) no C16 C17 C18 C19 . . . . 1(1) no C16 C17 C18 H18 . . . . -178(1) no C17 C16 C15 C20 . . . . 1(1) no C17 C18 C19 C20 . . . . 0(1) no C17 C18 C19 H19 . . . . 179(1) no C18 C17 C16 H16 . . . . 177(1) no C18 C19 C20 H20 . . . . 179.2(10) no C19 C18 C17 H17 . . . . -178(1) no C20 C15 C16 H16 . . . . -178.3(9) no C20 C19 C18 H18 . . . . 179(1) no H2 C2 C3 H31 . . . . -57(1) no H2 C2 C3 H32 . . . . 61(1) no H2 C2 C8 H81 . . . . -88.1(10) no H2 C2 C8 H82 . . . . 33(1) no H71 C7 C8 H81 . . . . 110.6(9) no H71 C7 C8 H82 . . . . -11(1) no H72 C7 C8 H81 . . . . -10(1) no H72 C7 C8 H82 . . . . -131.9(9) no H91 C9 C10 H101 . . . . -171.6(8) no H91 C9 C10 H102 . . . . -52(1) no H92 C9 C10 H101 . . . . 69(1) no H92 C9 C10 H102 . . . . -170.9(8) no H101 C10 C11 H111 . . . . 74(1) no H101 C10 C11 H112 . . . . -165(1) no H102 C10 C11 H111 . . . . -44(1) no H102 C10 C11 H112 . . . . 75(1) no H111 C11 C12 H121 . . . . 60(2) no H111 C11 C12 H122 . . . . -179(1) no H111 C11 C12 H123 . . . . -59(2) no H112 C11 C12 H121 . . . . -59(2) no H112 C11 C12 H122 . . . . 60(2) no H112 C11 C12 H123 . . . . -179(1) no H16 C16 C17 H17 . . . . -2(1) no H17 C17 C18 H18 . . . . 1(1) no H18 C18 C19 H19 . . . . 0(1) no H19 C19 C20 H20 . . . . 0(1) no #------------------------------------------------------------------------------