#Supplementary Material (ESI) for Chemical Communications #This journal is © the Royal Society of Chemistry 2006 data_global _audit_creation_method SHELXL-97 _journal_coden_Cambridge 182 loop_ _publ_author_name 'T. Back' 'Mitchell H.Weston' 'Masood Parvez' 'Katsumasa Nakajima' _publ_contact_author_name 'T.G. Back' _publ_contact_author_address ; Department of Chemistry University of Calgary 2500 University Drive NW Calgary Alberta T2N 1N4 CANADA ; _publ_contact_author_email TGBACK@UCALGARY.CA _publ_requested_journal 'Chemical Communications' _publ_section_title ; Ring-Expansion of Tertiary Cyclic a-Vinylamines by Tandem Conjugate Addition to (p-Toluenesulfonyl)ethyne and Formal 3-Aza-Cope Rearrangement ; #------------------------------------------------------------------------------ data_Compound_I _database_code_depnum_ccdc_archive 'CCDC 609578' #----------------------------------------------------------------------------- _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'HKL DENZO (Otwinowski & Minor, 1997)' _computing_data_reduction 'SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SAPI91 (Fan, 1991)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' #----------------------------------------------------------------------------- _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H27 N O2 S' _chemical_formula_weight 381.52 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 'P b c a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 17.003(4) _cell_length_b 11.331(4) _cell_length_c 21.365(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4116(2) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8795 _cell_measurement_theta_min 3.9 _cell_measurement_theta_max 27.4 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.231 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1632 _exptl_absorpt_coefficient_mu 0.175 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9693 _exptl_absorpt_correction_T_max 0.9794 _exptl_absorpt_process_details 'SORTAV: (Blessing, 1997)' _diffrn_ambient_temperature 173(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 'Nonius KappaCCD' _diffrn_measurement_method ' \w and \f ' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8795 _diffrn_reflns_av_R_equivalents 0.0224 _diffrn_reflns_av_sigmaI/netI 0.0330 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.91 _diffrn_reflns_theta_max 27.44 _reflns_number_total 4661 _reflns_number_gt 3640 _reflns_threshold_expression >2sigma(I) _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^)+(0.0560P)^2^+2.2000P] 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 4661 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0610 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.1181 _refine_ls_wR_factor_gt 0.1052 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.985 _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 S11 S 0.09142(2) 0.30732(3) 0.347884(18) 0.02786(12) Uani 1 1 d . . . O1 O 0.06258(7) 0.35107(11) 0.28857(5) 0.0351(3) Uani 1 1 d . . . O2 O 0.09247(7) 0.38849(10) 0.40000(6) 0.0361(3) Uani 1 1 d . . . N1 N 0.27167(8) 0.19189(14) 0.24890(6) 0.0350(3) Uani 1 1 d . . . C2 C 0.20812(9) 0.23754(16) 0.27778(8) 0.0312(4) Uani 1 1 d . . . H2 H 0.1679 0.2763 0.2538 0.037 Uiso 1 1 d R . . C3 C 0.18373(9) 0.24331(15) 0.33876(7) 0.0293(3) Uani 1 1 d . . . C4 C 0.21845(9) 0.19882(16) 0.39999(8) 0.0329(4) Uani 1 1 d . . . H4A H 0.1852 0.2221 0.4341 0.039 Uiso 1 1 d R . . H4B H 0.2219 0.1143 0.3987 0.039 Uiso 1 1 d R . . C5 C 0.29893(10) 0.24621(17) 0.41241(8) 0.0353(4) Uani 1 1 d . . . H5 H 0.3072 0.3299 0.4147 0.042 Uiso 1 1 d R . . C6 C 0.36171(10) 0.17684(17) 0.41971(8) 0.0367(4) Uani 1 1 d . . . H6 H 0.3544 0.0972 0.4338 0.044 Uiso 1 1 d R . . C7 C 0.44371(11) 0.21354(19) 0.40789(9) 0.0431(4) Uani 1 1 d . . . H7A H 0.4486 0.2971 0.4141 0.052 Uiso 1 1 d R . . H7B H 0.4780 0.1728 0.4363 0.052 Uiso 1 1 d R . . C8 C 0.46563(10) 0.18174(17) 0.34013(8) 0.0355(4) Uani 1 1 d . . . H8A H 0.5156 0.2159 0.3296 0.043 Uiso 1 1 d R . . H8B H 0.4685 0.0975 0.3359 0.043 Uiso 1 1 d R . . C9 C 0.40533(9) 0.22567(15) 0.29207(8) 0.0315(4) Uani 1 1 d . . . H9A H 0.3818 0.2974 0.3069 0.038 Uiso 1 1 d R . . H9B H 0.4314 0.2404 0.2530 0.038 Uiso 1 1 d R . . C10 C 0.33890(9) 0.13756(15) 0.28005(8) 0.0315(4) Uani 1 1 d . . . H10A H 0.3229 0.1054 0.3196 0.038 Uiso 1 1 d R . . H10B H 0.3595 0.0756 0.2541 0.038 Uiso 1 1 d R . . C12 C 0.02965(9) 0.18830(14) 0.37040(7) 0.0268(3) Uani 1 1 d . . . C13 C 0.01790(10) 0.09461(15) 0.32938(8) 0.0312(4) Uani 1 1 d . . . H13 H 0.0443 0.0935 0.2897 0.037 Uiso 1 1 d R . . C14 C -0.03168(10) 0.00324(15) 0.34645(8) 0.0340(4) Uani 1 1 d . . . H14 H -0.0402 -0.0617 0.3184 0.041 Uiso 1 1 d R . . C15 C -0.07003(10) 0.00352(15) 0.40394(8) 0.0347(4) Uani 1 1 d . . . C16 C -0.12414(11) -0.09636(18) 0.42203(11) 0.0478(5) Uani 1 1 d . . . H16A H -0.1261 -0.1543 0.3880 0.072 Uiso 0.50 1 calc PR . . H16B H -0.1771 -0.0653 0.4297 0.072 Uiso 0.50 1 calc PR . . H16C H -0.1044 -0.1343 0.4602 0.072 Uiso 0.50 1 calc PR . . H16D H -0.1457 -0.0816 0.4639 0.072 Uiso 0.50 1 calc PR . . H16E H -0.0946 -0.1707 0.4222 0.072 Uiso 0.50 1 calc PR . . H16F H -0.1673 -0.1017 0.3917 0.072 Uiso 0.50 1 calc PR . . C17 C -0.05718(11) 0.09747(16) 0.44438(9) 0.0390(4) Uani 1 1 d . . . H17 H -0.0835 0.0992 0.4841 0.047 Uiso 1 1 d R . . C18 C -0.00764(10) 0.18981(15) 0.42824(8) 0.0345(4) Uani 1 1 d . . . H18 H 0.0020 0.2539 0.4566 0.041 Uiso 1 1 d R . . C19 C 0.27690(10) 0.20587(18) 0.18115(8) 0.0378(4) Uani 1 1 d . . . H19A H 0.2626 0.2852 0.1702 0.045 Uiso 1 1 d R . . H19B H 0.3298 0.1906 0.1678 0.045 Uiso 1 1 d R . . C20 C 0.22406(9) 0.12496(15) 0.14380(8) 0.0308(4) Uani 1 1 d . . . C21 C 0.22283(11) 0.13750(16) 0.07887(8) 0.0376(4) Uani 1 1 d . . . H21 H 0.2566 0.1946 0.0594 0.045 Uiso 1 1 d R . . C22 C 0.17329(13) 0.06895(18) 0.04263(9) 0.0499(5) Uani 1 1 d . . . H22 H 0.1736 0.0771 -0.0021 0.060 Uiso 1 1 d R . . C23 C 0.12450(13) -0.01279(19) 0.07052(10) 0.0524(5) Uani 1 1 d . . . H23 H 0.0892 -0.0589 0.0454 0.063 Uiso 1 1 d R . . C24 C 0.12535(11) -0.02687(17) 0.13442(10) 0.0455(5) Uani 1 1 d . . . H24 H 0.0918 -0.0842 0.1539 0.055 Uiso 1 1 d R . . C25 C 0.17532(10) 0.04150(16) 0.17125(9) 0.0367(4) Uani 1 1 d . . . H25 H 0.1764 0.0315 0.2159 0.044 Uiso 1 1 d 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 S11 0.0287(2) 0.0273(2) 0.0276(2) 0.00006(15) -0.00282(15) -0.00006(15) O1 0.0347(6) 0.0373(7) 0.0333(6) 0.0075(5) -0.0056(5) 0.0012(5) O2 0.0406(7) 0.0301(6) 0.0375(7) -0.0077(5) -0.0039(5) -0.0006(5) N1 0.0286(7) 0.0525(9) 0.0237(7) -0.0023(6) -0.0005(5) -0.0012(6) C2 0.0281(7) 0.0382(9) 0.0272(8) 0.0015(7) -0.0039(6) -0.0044(7) C3 0.0264(7) 0.0323(8) 0.0292(8) 0.0020(7) -0.0016(6) -0.0008(6) C4 0.0319(8) 0.0389(9) 0.0277(8) 0.0027(7) 0.0003(6) 0.0042(7) C5 0.0365(9) 0.0439(10) 0.0255(8) -0.0040(7) -0.0031(7) 0.0012(8) C6 0.0404(9) 0.0442(10) 0.0255(8) 0.0026(7) -0.0032(7) 0.0035(8) C7 0.0400(10) 0.0538(12) 0.0356(10) -0.0032(9) -0.0062(8) 0.0061(9) C8 0.0274(8) 0.0410(10) 0.0382(9) -0.0013(8) -0.0015(7) -0.0003(7) C9 0.0281(8) 0.0349(9) 0.0316(8) -0.0001(7) 0.0010(6) -0.0018(7) C10 0.0302(8) 0.0352(9) 0.0290(8) -0.0048(7) 0.0021(6) 0.0004(7) C12 0.0255(7) 0.0286(8) 0.0262(8) -0.0004(6) -0.0024(6) 0.0014(6) C13 0.0353(8) 0.0326(9) 0.0258(8) -0.0026(7) -0.0007(6) 0.0011(7) C14 0.0378(9) 0.0290(8) 0.0352(9) -0.0037(7) -0.0059(7) 0.0001(7) C15 0.0288(8) 0.0336(9) 0.0416(10) 0.0056(8) -0.0031(7) 0.0007(7) C16 0.0388(10) 0.0395(10) 0.0650(13) 0.0075(9) 0.0031(9) -0.0066(8) C17 0.0399(9) 0.0433(10) 0.0337(9) 0.0002(8) 0.0083(7) -0.0020(8) C18 0.0377(9) 0.0358(9) 0.0300(8) -0.0059(7) 0.0022(7) -0.0012(7) C19 0.0333(9) 0.0544(11) 0.0256(8) -0.0006(8) 0.0015(7) -0.0079(8) C20 0.0283(8) 0.0351(9) 0.0288(8) -0.0024(7) -0.0010(6) 0.0062(7) C21 0.0465(10) 0.0363(9) 0.0302(9) -0.0011(7) -0.0029(7) 0.0063(8) C22 0.0691(13) 0.0468(11) 0.0339(10) -0.0063(9) -0.0152(9) 0.0076(10) C23 0.0557(12) 0.0455(11) 0.0559(13) -0.0139(10) -0.0187(10) 0.0004(10) C24 0.0402(10) 0.0374(10) 0.0589(13) -0.0091(9) 0.0001(9) -0.0020(8) C25 0.0342(9) 0.0398(10) 0.0360(9) -0.0021(8) 0.0013(7) 0.0026(7) 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 S11 O2 1.4443(12) . ? S11 O1 1.4465(12) . ? S11 C3 1.7400(16) . ? S11 C12 1.7758(17) . ? N1 C2 1.348(2) . ? N1 C10 1.459(2) . ? N1 C19 1.459(2) . ? C2 C3 1.369(2) . ? C2 H2 0.9599 . ? C3 C4 1.521(2) . ? C4 C5 1.494(2) . ? C4 H4A 0.9599 . ? C4 H4B 0.9601 . ? C5 C6 1.335(2) . ? C5 H5 0.9600 . ? C6 C7 1.477(3) . ? C6 H6 0.9600 . ? C7 C8 1.538(2) . ? C7 H7A 0.9600 . ? C7 H7B 0.9601 . ? C8 C9 1.534(2) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C9 C10 1.529(2) . ? C9 H9A 0.9600 . ? C9 H9B 0.9599 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C12 C18 1.389(2) . ? C12 C13 1.391(2) . ? C13 C14 1.384(2) . ? C13 H13 0.9601 . ? C14 C15 1.391(2) . ? C14 H14 0.9600 . ? C15 C17 1.388(3) . ? C15 C16 1.509(2) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C16 H16D 0.9800 . ? C16 H16E 0.9800 . ? C16 H16F 0.9800 . ? C17 C18 1.387(2) . ? C17 H17 0.9599 . ? C18 H18 0.9600 . ? C19 C20 1.511(2) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C20 C25 1.387(2) . ? C20 C21 1.395(2) . ? C21 C22 1.383(3) . ? C21 H21 0.9601 . ? C22 C23 1.379(3) . ? C22 H22 0.9601 . ? C23 C24 1.375(3) . ? C23 H23 0.9600 . ? C24 C25 1.393(3) . ? C24 H24 0.9599 . ? C25 H25 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 S11 O1 117.48(8) . . ? O2 S11 C3 109.91(8) . . ? O1 S11 C3 110.52(8) . . ? O2 S11 C12 106.39(8) . . ? O1 S11 C12 107.29(7) . . ? C3 S11 C12 104.32(8) . . ? C2 N1 C10 125.55(14) . . ? C2 N1 C19 117.48(14) . . ? C10 N1 C19 116.78(13) . . ? N1 C2 C3 134.20(16) . . ? N1 C2 H2 120.1 . . ? C3 C2 H2 105.7 . . ? C2 C3 C4 133.24(15) . . ? C2 C3 S11 113.57(12) . . ? C4 C3 S11 113.07(11) . . ? C5 C4 C3 112.90(14) . . ? C5 C4 H4A 107.8 . . ? C3 C4 H4A 109.5 . . ? C5 C4 H4B 107.9 . . ? C3 C4 H4B 109.2 . . ? H4A C4 H4B 109.5 . . ? C6 C5 C4 122.80(17) . . ? C6 C5 H5 117.3 . . ? C4 C5 H5 119.9 . . ? C5 C6 C7 124.70(18) . . ? C5 C6 H6 119.1 . . ? C7 C6 H6 116.2 . . ? C6 C7 C8 108.89(15) . . ? C6 C7 H7A 109.7 . . ? C8 C7 H7A 109.9 . . ? C6 C7 H7B 109.3 . . ? C8 C7 H7B 109.6 . . ? H7A C7 H7B 109.5 . . ? C9 C8 C7 113.08(14) . . ? C9 C8 H8A 107.7 . . ? C7 C8 H8A 109.9 . . ? C9 C8 H8B 107.1 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C10 C9 C8 113.22(14) . . ? C10 C9 H9A 107.5 . . ? C8 C9 H9A 109.4 . . ? C10 C9 H9B 108.0 . . ? C8 C9 H9B 109.2 . . ? H9A C9 H9B 109.5 . . ? N1 C10 C9 112.32(14) . . ? N1 C10 H10A 109.9 . . ? C9 C10 H10A 108.0 . . ? N1 C10 H10B 109.3 . . ? C9 C10 H10B 107.8 . . ? H10A C10 H10B 109.5 . . ? C18 C12 C13 120.30(15) . . ? C18 C12 S11 120.10(12) . . ? C13 C12 S11 119.59(12) . . ? C14 C13 C12 119.49(15) . . ? C14 C13 H13 120.5 . . ? C12 C13 H13 120.0 . . ? C13 C14 C15 121.10(16) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 118.8 . . ? C17 C15 C14 118.54(16) . . ? C17 C15 C16 120.77(17) . . ? C14 C15 C16 120.69(17) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C16 H16D 109.5 . . ? H16A C16 H16D 141.1 . . ? H16B C16 H16D 56.3 . . ? H16C C16 H16D 56.3 . . ? C15 C16 H16E 109.5 . . ? H16A C16 H16E 56.3 . . ? H16B C16 H16E 141.1 . . ? H16C C16 H16E 56.3 . . ? H16D C16 H16E 109.5 . . ? C15 C16 H16F 109.5 . . ? H16A C16 H16F 56.3 . . ? H16B C16 H16F 56.3 . . ? H16C C16 H16F 141.1 . . ? H16D C16 H16F 109.5 . . ? H16E C16 H16F 109.5 . . ? C18 C17 C15 121.29(16) . . ? C18 C17 H17 119.2 . . ? C15 C17 H17 119.5 . . ? C17 C18 C12 119.28(16) . . ? C17 C18 H18 121.1 . . ? C12 C18 H18 119.6 . . ? N1 C19 C20 114.95(14) . . ? N1 C19 H19A 109.1 . . ? C20 C19 H19A 106.8 . . ? N1 C19 H19B 109.5 . . ? C20 C19 H19B 106.9 . . ? H19A C19 H19B 109.5 . . ? C25 C20 C21 118.75(16) . . ? C25 C20 C19 123.04(15) . . ? C21 C20 C19 118.18(16) . . ? C22 C21 C20 120.59(18) . . ? C22 C21 H21 120.0 . . ? C20 C21 H21 119.4 . . ? C23 C22 C21 120.12(19) . . ? C23 C22 H22 119.9 . . ? C21 C22 H22 120.0 . . ? C24 C23 C22 120.05(19) . . ? C24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C23 C24 C25 120.2(2) . . ? C23 C24 H24 120.2 . . ? C25 C24 H24 119.6 . . ? C20 C25 C24 120.29(18) . . ? C20 C25 H25 119.3 . . ? C24 C25 H25 120.4 . . ? 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 C10 N1 C2 C3 -4.0(3) . . . . ? C19 N1 C2 C3 -178.98(19) . . . . ? N1 C2 C3 C4 -0.7(3) . . . . ? N1 C2 C3 S11 -176.44(16) . . . . ? O2 S11 C3 C2 -136.41(13) . . . . ? O1 S11 C3 C2 -5.15(16) . . . . ? C12 S11 C3 C2 109.87(13) . . . . ? O2 S11 C3 C4 46.98(14) . . . . ? O1 S11 C3 C4 178.24(12) . . . . ? C12 S11 C3 C4 -66.74(14) . . . . ? C2 C3 C4 C5 57.8(3) . . . . ? S11 C3 C4 C5 -126.50(14) . . . . ? C3 C4 C5 C6 -120.69(18) . . . . ? C4 C5 C6 C7 155.23(17) . . . . ? C5 C6 C7 C8 -92.8(2) . . . . ? C6 C7 C8 C9 50.6(2) . . . . ? C7 C8 C9 C10 -88.48(19) . . . . ? C2 N1 C10 C9 -93.34(19) . . . . ? C19 N1 C10 C9 81.63(18) . . . . ? C8 C9 C10 N1 163.74(14) . . . . ? O2 S11 C12 C18 1.72(15) . . . . ? O1 S11 C12 C18 -124.80(14) . . . . ? C3 S11 C12 C18 117.92(14) . . . . ? O2 S11 C12 C13 -179.29(12) . . . . ? O1 S11 C12 C13 54.18(15) . . . . ? C3 S11 C12 C13 -63.09(14) . . . . ? C18 C12 C13 C14 0.5(2) . . . . ? S11 C12 C13 C14 -178.53(13) . . . . ? C12 C13 C14 C15 0.0(2) . . . . ? C13 C14 C15 C17 -0.4(3) . . . . ? C13 C14 C15 C16 179.83(16) . . . . ? C14 C15 C17 C18 0.3(3) . . . . ? C16 C15 C17 C18 -179.94(17) . . . . ? C15 C17 C18 C12 0.2(3) . . . . ? C13 C12 C18 C17 -0.6(2) . . . . ? S11 C12 C18 C17 178.43(13) . . . . ? C2 N1 C19 C20 -75.8(2) . . . . ? C10 N1 C19 C20 108.77(17) . . . . ? N1 C19 C20 C25 -1.4(2) . . . . ? N1 C19 C20 C21 176.71(15) . . . . ? C25 C20 C21 C22 0.7(3) . . . . ? C19 C20 C21 C22 -177.46(17) . . . . ? C20 C21 C22 C23 0.0(3) . . . . ? C21 C22 C23 C24 -0.4(3) . . . . ? C22 C23 C24 C25 0.1(3) . . . . ? C21 C20 C25 C24 -1.0(2) . . . . ? C19 C20 C25 C24 177.10(17) . . . . ? C23 C24 C25 C20 0.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.420 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.042