# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Jose Mascarenas' _publ_contact_author_email JOSELUIS.MASCARENAS@USC.ES _publ_section_title ; Palladium-Catalyzed [3C+2C+2C] Cycloaddition of Enynilydenecyclopropanes: Efficient Construction of Fused 5-7-5 Tricyclic Systems ; loop_ _publ_author_name 'Jose Mascarenas' 'Marisel Araya' 'Gaurav Bhargava' 'Luis Castedoa' 'Fernando Lopez' 'Beatriz Trillo' # Attachment 'ccdc_deposit_mascarenas.cif' data_lm05bt1n _database_code_depnum_ccdc_archive 'CCDC 748242' #TrackingRef 'ccdc_deposit_mascarenas.cif' _audit_creation_date 2009-06-24T16:45:29-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C19 H23 N O3 S' _chemical_formula_sum 'C19 H23 N O3 S' _chemical_formula_weight 345.45 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'R -3' _symmetry_space_group_name_Hall '-R 3' _symmetry_Int_Tables_number 148 loop_ _space_group_symop_operation_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 23.895(2) _cell_length_b 23.895(2) _cell_length_c 15.255(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_volume 7543.4(17) _cell_formula_units_Z 18 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 937 _cell_measurement_theta_min 2.84 _cell_measurement_theta_max 23.01 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.16 _exptl_crystal_density_diffrn 1.369 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3312 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.21 _exptl_absorpt_correction_T_max 0.967 _exptl_absorpt_correction_T_min 0.808 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'BRUKER SADABS' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_probe x-ray _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromador graphite _diffrn_measurement_device_type 'Smart-CCD-1000 BRUKER' _diffrn_measurement_method 'omega scans' _diffrn_reflns_av_R_equivalents 0.0752 _diffrn_reflns_av_unetI/netI 0.0557 _diffrn_reflns_number 24562 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.98 _diffrn_measured_fraction_theta_max 0.98 _reflns_number_total 3373 _reflns_number_gt 2224 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection "'BRUKER Smart" _computing_cell_refinement "'BRUKER Smart" _computing_data_reduction "'BRUKER Saint" _computing_structure_solution 'SIR97 (Altomare et all, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(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^)+(0.0450P)^2^+1.6767P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3373 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0788 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.1113 _refine_ls_wR_factor_gt 0.0948 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.315 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.057 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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 0.13931(11) 0.14558(11) 0.23928(15) 0.0238(5) Uani 1 1 d . . . H1 H 0.1755 0.1914 0.2378 0.029 Uiso 1 1 calc R . . C2 C 0.13325(11) 0.12137(11) 0.33234(15) 0.0237(5) Uani 1 1 d . . . C3 C 0.19307(11) 0.12572(12) 0.37249(16) 0.0284(5) Uani 1 1 d . . . H3A H 0.1845 0.1144 0.4354 0.034 Uiso 1 1 calc R . . H3B H 0.2285 0.1712 0.369 0.034 Uiso 1 1 calc R . . C4 C 0.21652(11) 0.08290(11) 0.33094(15) 0.0256(5) Uani 1 1 d . . . H4A H 0.1795 0.0384 0.3257 0.031 Uiso 1 1 calc R . . H4B H 0.2487 0.0815 0.3703 0.031 Uiso 1 1 calc R . . C5 C 0.24693(10) 0.10602(11) 0.24039(15) 0.0231(5) Uani 1 1 d . . . H5 H 0.2775 0.1537 0.2428 0.028 Uiso 1 1 calc R . . C6 C 0.19795(10) 0.09204(10) 0.16870(14) 0.0196(5) Uani 1 1 d . . . C7 C 0.15250(10) 0.10841(10) 0.16908(15) 0.0208(5) Uani 1 1 d . . . C8 C 0.10582(11) 0.09592(11) 0.09559(16) 0.0258(5) Uani 1 1 d . . . H8A H 0.1278 0.1038 0.0381 0.031 Uiso 1 1 calc R . . H8B H 0.0696 0.0507 0.0974 0.031 Uiso 1 1 calc R . . O9 O 0.08280(8) 0.14009(8) 0.10936(11) 0.0306(4) Uani 1 1 d . . . C10 C 0.07897(12) 0.14421(13) 0.20233(15) 0.0300(6) Uani 1 1 d . . . H10A H 0.0393 0.1064 0.2251 0.036 Uiso 1 1 calc R . . H10B H 0.0784 0.184 0.2188 0.036 Uiso 1 1 calc R . . C11 C 0.08019(13) 0.09980(14) 0.37978(19) 0.0356(6) Uani 1 1 d . . . C12 C 0.20746(10) 0.05485(10) 0.09603(14) 0.0202(5) Uani 1 1 d . . . H12A H 0.1751 0.0082 0.0993 0.024 Uiso 1 1 calc R . . H12B H 0.2048 0.0716 0.0378 0.024 Uiso 1 1 calc R . . N13 N 0.27360(8) 0.06664(8) 0.11356(12) 0.0210(4) Uani 1 1 d . . . C14 C 0.28367(11) 0.07255(11) 0.20974(15) 0.0251(5) Uani 1 1 d . . . H14A H 0.3302 0.0988 0.2241 0.03 Uiso 1 1 calc R . . H14B H 0.266 0.0295 0.2373 0.03 Uiso 1 1 calc R . . S15 S 0.29531(3) 0.02065(3) 0.06133(4) 0.02292(16) Uani 1 1 d . . . O16 O 0.27102(8) 0.01394(8) -0.02633(10) 0.0292(4) Uani 1 1 d . . . O17 O 0.36306(7) 0.04766(7) 0.07570(11) 0.0293(4) Uani 1 1 d . . . C18 C 0.25495(10) -0.05528(10) 0.11326(15) 0.0211(5) Uani 1 1 d . . . C19 C 0.28480(10) -0.06839(11) 0.18224(15) 0.0221(5) Uani 1 1 d . . . H19 H 0.3277 -0.0376 0.1988 0.027 Uiso 1 1 calc R . . C20 C 0.25163(11) -0.12658(11) 0.22650(15) 0.0238(5) Uani 1 1 d . . . H20 H 0.2726 -0.1357 0.2725 0.029 Uiso 1 1 calc R . . C21 C 0.18808(11) -0.17205(11) 0.20493(15) 0.0239(5) Uani 1 1 d . . . C22 C 0.15878(11) -0.15769(11) 0.13649(16) 0.0272(5) Uani 1 1 d . . . H22 H 0.1155 -0.1881 0.121 0.033 Uiso 1 1 calc R . . C23 C 0.19132(11) -0.10018(11) 0.09048(16) 0.0252(5) Uani 1 1 d . . . H23 H 0.1706 -0.0913 0.0438 0.03 Uiso 1 1 calc R . . C24 C 0.15324(12) -0.23465(12) 0.25402(17) 0.0330(6) Uani 1 1 d . . . H24A H 0.1075 -0.2474 0.2599 0.049 Uiso 1 1 calc R . . H24B H 0.1724 -0.2293 0.3124 0.049 Uiso 1 1 calc R . . H24C H 0.1569 -0.2682 0.2219 0.049 Uiso 1 1 calc R . . H11A H 0.0817(13) 0.0889(13) 0.442(2) 0.046(8) Uiso 1 1 d . . . H11B H 0.0405(13) 0.0973(13) 0.3593(17) 0.041(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 C1 0.0262(12) 0.0247(12) 0.0236(13) -0.0015(10) 0.0009(10) 0.0148(10) C2 0.0279(12) 0.0243(12) 0.0235(13) -0.0040(10) -0.0017(10) 0.0164(10) C3 0.0301(13) 0.0371(14) 0.0228(13) -0.0062(11) -0.0055(10) 0.0203(11) C4 0.0254(12) 0.0320(13) 0.0229(13) -0.0021(10) -0.0051(10) 0.0170(11) C5 0.0193(11) 0.0237(11) 0.0263(13) -0.0051(10) -0.0034(9) 0.0107(10) C6 0.0213(11) 0.0182(11) 0.0186(12) 0.0003(9) 0.0017(9) 0.0093(9) C7 0.0233(11) 0.0199(11) 0.0188(12) 0.0005(9) 0.0005(9) 0.0105(9) C8 0.0283(12) 0.0300(13) 0.0257(13) -0.0006(10) -0.0014(10) 0.0196(11) O9 0.0402(10) 0.0462(10) 0.0222(9) -0.0026(8) -0.0029(7) 0.0341(9) C10 0.0366(14) 0.0416(15) 0.0233(14) -0.0005(11) -0.0004(11) 0.0280(12) C11 0.0343(15) 0.0515(17) 0.0287(16) 0.0070(12) 0.0035(12) 0.0272(13) C12 0.0214(11) 0.0205(11) 0.0193(12) 0.0005(9) 0.0004(9) 0.0111(9) N13 0.0197(9) 0.0215(9) 0.0238(11) -0.0028(8) 0.0002(8) 0.0117(8) C14 0.0243(12) 0.0303(13) 0.0242(13) -0.0059(10) -0.0044(10) 0.0162(11) S15 0.0236(3) 0.0226(3) 0.0252(3) -0.0009(2) 0.0040(2) 0.0135(3) O16 0.0413(10) 0.0313(9) 0.0201(9) -0.0014(7) 0.0027(7) 0.0220(8) O17 0.0219(8) 0.0264(9) 0.0400(11) 0.0015(7) 0.0079(7) 0.0123(7) C18 0.0221(11) 0.0189(11) 0.0249(13) -0.0032(9) 0.0031(9) 0.0122(9) C19 0.0160(11) 0.0258(12) 0.0242(12) -0.0044(10) -0.0002(9) 0.0101(10) C20 0.0248(12) 0.0288(13) 0.0192(12) -0.0023(10) -0.0003(9) 0.0144(10) C21 0.0231(12) 0.0237(12) 0.0241(13) -0.0039(10) 0.0044(9) 0.0110(10) C22 0.0199(11) 0.0242(12) 0.0345(15) -0.0094(10) -0.0030(10) 0.0089(10) C23 0.0252(12) 0.0256(12) 0.0289(14) -0.0081(10) -0.0060(10) 0.0157(10) C24 0.0342(14) 0.0313(14) 0.0290(15) -0.0031(11) 0.0031(11) 0.0131(12) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.512(3) . ? C1 C7 1.522(3) . ? C1 C10 1.533(3) . ? C1 H1 1 . ? C2 C11 1.320(3) . ? C2 C3 1.510(3) . ? C3 C4 1.528(3) . ? C3 H3A 0.99 . ? C3 H3B 0.99 . ? C4 C5 1.530(3) . ? C4 H4A 0.99 . ? C4 H4B 0.99 . ? C5 C6 1.512(3) . ? C5 C14 1.527(3) . ? C5 H5 1 . ? C6 C7 1.325(3) . ? C6 C12 1.508(3) . ? C7 C8 1.502(3) . ? C8 O9 1.429(3) . ? C8 H8A 0.99 . ? C8 H8B 0.99 . ? O9 C10 1.428(3) . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C11 H11A 0.99(3) . ? C11 H11B 0.97(3) . ? C12 N13 1.485(3) . ? C12 H12A 0.99 . ? C12 H12B 0.99 . ? N13 C14 1.482(3) . ? N13 S15 1.6376(18) . ? C14 H14A 0.99 . ? C14 H14B 0.99 . ? S15 O17 1.4284(17) . ? S15 O16 1.4345(17) . ? S15 C18 1.761(2) . ? C18 C19 1.392(3) . ? C18 C23 1.397(3) . ? C19 C20 1.384(3) . ? C19 H19 0.95 . ? C20 C21 1.395(3) . ? C20 H20 0.95 . ? C21 C22 1.392(3) . ? C21 C24 1.499(3) . ? C22 C23 1.385(3) . ? C22 H22 0.95 . ? C23 H23 0.95 . ? C24 H24A 0.98 . ? C24 H24B 0.98 . ? C24 H24C 0.98 . ? 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 C7 116.45(18) . . ? C2 C1 C10 115.33(19) . . ? C7 C1 C10 101.29(18) . . ? C2 C1 H1 107.7 . . ? C7 C1 H1 107.7 . . ? C10 C1 H1 107.7 . . ? C11 C2 C3 119.7(2) . . ? C11 C2 C1 123.6(2) . . ? C3 C2 C1 116.62(19) . . ? C2 C3 C4 115.91(19) . . ? C2 C3 H3A 108.3 . . ? C4 C3 H3A 108.3 . . ? C2 C3 H3B 108.3 . . ? C4 C3 H3B 108.3 . . ? H3A C3 H3B 107.4 . . ? C3 C4 C5 113.56(19) . . ? C3 C4 H4A 108.9 . . ? C5 C4 H4A 108.9 . . ? C3 C4 H4B 108.9 . . ? C5 C4 H4B 108.9 . . ? H4A C4 H4B 107.7 . . ? C6 C5 C14 104.31(18) . . ? C6 C5 C4 113.44(18) . . ? C14 C5 C4 112.40(19) . . ? C6 C5 H5 108.8 . . ? C14 C5 H5 108.8 . . ? C4 C5 H5 108.8 . . ? C7 C6 C12 124.4(2) . . ? C7 C6 C5 126.1(2) . . ? C12 C6 C5 109.51(17) . . ? C6 C7 C8 125.1(2) . . ? C6 C7 C1 127.9(2) . . ? C8 C7 C1 106.93(18) . . ? O9 C8 C7 105.39(18) . . ? O9 C8 H8A 110.7 . . ? C7 C8 H8A 110.7 . . ? O9 C8 H8B 110.7 . . ? C7 C8 H8B 110.7 . . ? H8A C8 H8B 108.8 . . ? C10 O9 C8 104.99(17) . . ? O9 C10 C1 105.94(18) . . ? O9 C10 H10A 110.5 . . ? C1 C10 H10A 110.5 . . ? O9 C10 H10B 110.5 . . ? C1 C10 H10B 110.5 . . ? H10A C10 H10B 108.7 . . ? C2 C11 H11A 118.3(16) . . ? C2 C11 H11B 124.4(16) . . ? H11A C11 H11B 117(2) . . ? N13 C12 C6 102.46(17) . . ? N13 C12 H12A 111.3 . . ? C6 C12 H12A 111.3 . . ? N13 C12 H12B 111.3 . . ? C6 C12 H12B 111.3 . . ? H12A C12 H12B 109.2 . . ? C14 N13 C12 107.64(16) . . ? C14 N13 S15 117.06(14) . . ? C12 N13 S15 116.71(14) . . ? N13 C14 C5 104.17(17) . . ? N13 C14 H14A 110.9 . . ? C5 C14 H14A 110.9 . . ? N13 C14 H14B 110.9 . . ? C5 C14 H14B 110.9 . . ? H14A C14 H14B 108.9 . . ? O17 S15 O16 119.83(10) . . ? O17 S15 N13 106.85(9) . . ? O16 S15 N13 106.40(10) . . ? O17 S15 C18 108.04(10) . . ? O16 S15 C18 108.77(10) . . ? N13 S15 C18 106.16(10) . . ? C19 C18 C23 119.9(2) . . ? C19 C18 S15 119.59(17) . . ? C23 C18 S15 120.30(18) . . ? C20 C19 C18 119.6(2) . . ? C20 C19 H19 120.2 . . ? C18 C19 H19 120.2 . . ? C19 C20 C21 121.4(2) . . ? C19 C20 H20 119.3 . . ? C21 C20 H20 119.3 . . ? C22 C21 C20 118.1(2) . . ? C22 C21 C24 121.6(2) . . ? C20 C21 C24 120.3(2) . . ? C23 C22 C21 121.5(2) . . ? C23 C22 H22 119.2 . . ? C21 C22 H22 119.2 . . ? C22 C23 C18 119.4(2) . . ? C22 C23 H23 120.3 . . ? C18 C23 H23 120.3 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 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 C7 C1 C2 C11 -118.0(3) . . . . ? C10 C1 C2 C11 0.5(3) . . . . ? C7 C1 C2 C3 64.9(3) . . . . ? C10 C1 C2 C3 -176.5(2) . . . . ? C11 C2 C3 C4 116.7(3) . . . . ? C1 C2 C3 C4 -66.1(3) . . . . ? C2 C3 C4 C5 72.1(3) . . . . ? C3 C4 C5 C6 -75.3(2) . . . . ? C3 C4 C5 C14 166.68(19) . . . . ? C14 C5 C6 C7 175.9(2) . . . . ? C4 C5 C6 C7 53.3(3) . . . . ? C14 C5 C6 C12 -2.9(2) . . . . ? C4 C5 C6 C12 -125.6(2) . . . . ? C12 C6 C7 C8 -3.5(3) . . . . ? C5 C6 C7 C8 177.8(2) . . . . ? C12 C6 C7 C1 179.9(2) . . . . ? C5 C6 C7 C1 1.2(4) . . . . ? C2 C1 C7 C6 -50.7(3) . . . . ? C10 C1 C7 C6 -176.7(2) . . . . ? C2 C1 C7 C8 132.2(2) . . . . ? C10 C1 C7 C8 6.3(2) . . . . ? C6 C7 C8 O9 -159.9(2) . . . . ? C1 C7 C8 O9 17.3(2) . . . . ? C7 C8 O9 C10 -35.7(2) . . . . ? C8 O9 C10 C1 40.5(2) . . . . ? C2 C1 C10 O9 -154.69(19) . . . . ? C7 C1 C10 O9 -28.0(2) . . . . ? C7 C6 C12 N13 163.6(2) . . . . ? C5 C6 C12 N13 -17.6(2) . . . . ? C6 C12 N13 C14 32.5(2) . . . . ? C6 C12 N13 S15 166.51(14) . . . . ? C12 N13 C14 C5 -35.1(2) . . . . ? S15 N13 C14 C5 -168.88(14) . . . . ? C6 C5 C14 N13 22.5(2) . . . . ? C4 C5 C14 N13 145.77(18) . . . . ? C14 N13 S15 O17 -60.47(18) . . . . ? C12 N13 S15 O17 169.88(15) . . . . ? C14 N13 S15 O16 170.42(16) . . . . ? C12 N13 S15 O16 40.77(18) . . . . ? C14 N13 S15 C18 54.66(18) . . . . ? C12 N13 S15 C18 -74.98(17) . . . . ? O17 S15 C18 C19 23.2(2) . . . . ? O16 S15 C18 C19 154.78(17) . . . . ? N13 S15 C18 C19 -91.08(19) . . . . ? O17 S15 C18 C23 -162.07(17) . . . . ? O16 S15 C18 C23 -30.5(2) . . . . ? N13 S15 C18 C23 83.61(19) . . . . ? C23 C18 C19 C20 1.5(3) . . . . ? S15 C18 C19 C20 176.19(17) . . . . ? C18 C19 C20 C21 -1.6(3) . . . . ? C19 C20 C21 C22 0.8(3) . . . . ? C19 C20 C21 C24 -179.9(2) . . . . ? C20 C21 C22 C23 0.2(3) . . . . ? C24 C21 C22 C23 -179.2(2) . . . . ? C21 C22 C23 C18 -0.2(3) . . . . ? C19 C18 C23 C22 -0.6(3) . . . . ? S15 C18 C23 C22 -175.25(17) . . . . ? # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF