# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Mark Moloney' 'Muhammed Anwar' 'Jonathan H. Bailey' 'Laura C. Dickinson' 'Hermia J. Edwards' 'Rajesh Goswami' _publ_contact_author_name 'Dr Mark Moloney' _publ_contact_author_address ; Chemistry University of Oxford Dyson Perrins Laboratory South Parks Rd Oxford OX1 3QY UNITED KINGDOM ; _publ_contact_author_email MARK.MOLONEY@CHEM.OX.AC.UK _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Pyrrolidinones Derived from (S)-Pyroglutamic Acid: Part 5. Penmacric Acid and Analogues ; _publ_section_references ; # SIR92 # Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 # Chebychev Weights # Carruthers, J.R. and Watkin, D.J. (1979), Acta Cryst, A35, 698-699 # Denzo # Otwinowski, Z. & Minor, W. (1996), Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press. # Extinction correction # Larson, A.C. (1970), Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294 # Azimutal absorption correction # North, A.C.T., Phillips, D.C. and Mathews, F.S., (1968), Acta Cryst, A24, 351-359 # SHELXS 86 # Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of Gottingen, Federal Republic of Germany. # DIFABS # Walker, N., and Stuart, D. Acta Cryst, (1983) A39, 158-166 # CRYSTALS # Watkin, D.J., Prout, C.K. Carruthers, J.R. & Betteridge, P.W. (1996) CRYSTALS Issue 10. Chemical Crystallography Laboratory, OXFORD, UK. #CAMERON # Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. # RC93 # Watkin, D.J., Prout, C.K., Lilley, P.M.deQ. (1994), RC93, Chemical Crystallography Laboratory, Oxford, UK. ; data_CRYSTALS_cif _database_code_CSD 208237 _audit_creation_date 99-07-12 _audit_creation_method CRYSTALS_ver_12-03-99 #========================================================================== # Diffractometer details #========================================================================== # choose from: #++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++ CAD4 _diffrn_measurement_device_type ' Enraf-nonius CAD4 ' _diffrn_radiation_monochromator graphite _computing_data_collection 'CAD-4 software (Enraf-Nonius, 1989)' _computing_data_reduction ; RC93 (Watkin, D.J., Prout, C.K., Lilley, P.M.deQ. 1994) ; _computing_cell_refinement 'CAD-4 software (Enraf-Nonius, 1989)' # or #++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++ DIP 2000 #++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++ STOE IPDS #_diffrn_measurement_device-type 'Stoe IPDS ' #_computing_data_collection 'Stoe IPDS software (Stoe, 1996)' #_computing_data_reduction 'XRED (Stoe, 1.08, 1996)' #_computing_cell_refinement 'Stoe IPDS software (Stoe, 1996)' # end_choice #========================================================================== # General computing #========================================================================== _computing_structure_refinement ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) ; _computing_publication_material ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) ; _computing_molecular_graphics ; CAMERON (Watkin, Prout & Pearce, 1996) ; # choose one of the following two lines # _computing_structure_solution 'SHELXS86 (Sheldrick, 1986)' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' #========================================================================== _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point 'not measured' # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment noref #**************************************************************************** _cell_length_a 14.089(3) _cell_angle_alpha 90 _cell_length_b 6.305(2) _cell_angle_beta 90 _cell_length_c 25.875(5) _cell_angle_gamma 90 _cell_volume 2298.5 _symmetry_cell_setting 'Orthorhombic ' _symmetry_space_group_name_H-M 'P 21 21 21 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0170 0.0090 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0290 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0470 0.0320 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B 'S ' 0.3190 0.5570 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 International_Tables_Vol_IV_Table_2.2B _chemical_formula_sum ' C26 H26 N2 O4 S1 ' _chemical_formula_moiety ' C26 H26 N2 O4 S1 ' _chemical_compound_source ; ? ; _chemical_formula_weight 462.56 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 20 _cell_measurement_theta_max 38 _cell_measurement_temperature 150 _cell_formula_units_Z 4 _exptl_crystal_description ' needle ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.12 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_max 0.64 _exptl_crystal_density_diffrn 1.34 _exptl_crystal_density_meas 'not measured' _exptl_crystal_F_000 979.89 _exptl_absorpt_coefficient_mu 1.55 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '\y scan,(North et al, 1968)' _exptl_absorpt_correction_T_min 0.75 _exptl_absorpt_correction_T_max 0.83 # Sheldrick geometric definitions 0.78 0.83 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 3 _diffrn_standards_decay_% 3.14 _diffrn_ambient_temperature 150 _diffrn_reflns_number 5235 _reflns_number_total 2699 _diffrn_reflns_av_R_equivalents 0.03 # Number of reflections with Friedels Law is 2699 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2345 _diffrn_measured_fraction_theta_max 1.000 _reflns_number_gt 2160 _diffrn_reflns_theta_min 0.00 _diffrn_reflns_theta_max 74.33 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 32 _reflns_limit_h_min 0 _reflns_limit_h_max 17 _reflns_limit_k_min 0 _reflns_limit_k_max 7 _reflns_limit_l_min 0 _reflns_limit_l_max 32 _refine_diff_density_min -0.87 _refine_diff_density_max 1.25 _reflns_threshold_expression >3.00\s(I) _refine_ls_number_reflns 2160 _refine_ls_number_parameters 298 _refine_ls_R_factor_gt 0.1136 _refine_ls_wR_factor_ref 0.1407 _refine_ls_goodness_of_fit_ref 0.9854 _refine_ls_shift/su_max 0.081033 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 4 parameters, Carruthers & Watkin , 1979, 6.64 1.19 4.10 -1.19 ; _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54180 _diffrn_measurement_method \w/2\q # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 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_adp_type S1 1.23069(18) -0.0396(4) 0.26245(9) 0.0524 1.0000 Uani O2 1.0448(4) 0.6463(8) 0.17667(19) 0.0341 1.0000 Uani N3 0.9779(4) 0.434(1) 0.1157(2) 0.0326 1.0000 Uani O4 1.2341(6) -0.2604(13) 0.2695(3) 0.0662 1.0000 Uani O5 0.8526(4) 0.4593(16) 0.0612(2) 0.0672 1.0000 Uani C6 1.0160(5) 0.4726(11) 0.1617(2) 0.0287 1.0000 Uani C7 0.9922(6) 0.6494(15) 0.0365(3) 0.0427 1.0000 Uani C9 1.1827(6) 0.0427(15) 0.1102(3) 0.0435 1.0000 Uani C10 1.1822(5) 0.2092(13) 0.1454(2) 0.0330 1.0000 Uani N11 1.1427(6) 0.0033(12) 0.2230(3) 0.0509 1.0000 Uani C12 1.2354(6) 0.3903(13) 0.1349(3) 0.0377 1.0000 Uani C13 1.1296(5) 0.2047(13) 0.1957(3) 0.0336 1.0000 Uani C14 1.2375(7) 0.0583(17) 0.0668(3) 0.0522 1.0000 Uani C15 1.0766(7) 0.5506(19) 0.0243(4) 0.0584 1.0000 Uani C16 1.4957(6) 0.1636(18) 0.1720(3) 0.0489 1.0000 Uani C17 0.9410(7) 0.2123(15) 0.1115(4) 0.0527 1.0000 Uani C18 1.0229(6) 0.2680(13) 0.1923(3) 0.0352 1.0000 Uani C19 0.8418(7) 0.274(2) 0.0924(4) 0.0592 1.0000 Uani C20 1.4601(7) 0.3063(18) 0.2093(4) 0.0536 1.0000 Uani C21 1.3362(6) 0.047(2) 0.2281(3) 0.0579 1.0000 Uani C22 1.0158(7) 0.8953(17) -0.0335(4) 0.0554 1.0000 Uani C23 1.2902(7) 0.3994(16) 0.0904(3) 0.0480 1.0000 Uani C24 1.2916(7) 0.2350(18) 0.0562(3) 0.0536 1.0000 Uani C25 0.9614(7) 0.8217(17) 0.0077(4) 0.0531 1.0000 Uani C26 0.9302(6) 0.5816(14) 0.0817(3) 0.0416 1.0000 Uani C27 0.9569(7) 0.1146(14) 0.1630(5) 0.0596 1.0000 Uani C28 1.1010(7) 0.794(2) -0.0450(4) 0.0600 1.0000 Uani C29 1.3710(6) -0.0767(18) 0.1930(3) 0.0519 1.0000 Uani C30 1.3770(9) 0.247(2) 0.2372(3) 0.0765 1.0000 Uani C31 1.4501(7) -0.0214(14) 0.1654(3) 0.0461 1.0000 Uani C32 1.1322(8) 0.629(2) -0.0168(4) 0.0671 1.0000 Uani C33 1.5843(8) 0.225(3) 0.1424(5) 0.0849 1.0000 Uani O8 1.2283(6) 0.1207(14) 0.2930(6) 0.1172 1.0000 Uani H91 1.1420 -0.0869 0.1175 0.0493 1.0000 Uiso H121 1.2351 0.5140 0.1604 0.0444 1.0000 Uiso H131 1.1583 0.3180 0.2187 0.0469 1.0000 Uiso H141 1.2381 -0.0639 0.0409 0.0524 1.0000 Uiso H151 1.0998 0.4352 0.0484 0.0648 1.0000 Uiso H171 0.9670 0.1033 0.0876 0.0541 1.0000 Uiso H181 1.0033 0.2672 0.2296 0.0489 1.0000 Uiso H191 0.7992 0.3015 0.1229 0.0664 1.0000 Uiso H192 0.8139 0.1503 0.0723 0.0664 1.0000 Uiso H201 1.4927 0.4477 0.2160 0.0630 1.0000 Uiso H221 0.9967 1.0192 -0.0551 0.0699 1.0000 Uiso H231 1.3298 0.5273 0.0828 0.0564 1.0000 Uiso H241 1.3310 0.2422 0.0239 0.0575 1.0000 Uiso H251 0.8975 0.8870 0.0154 0.0610 1.0000 Uiso H261 0.9123 0.7174 0.1005 0.0473 1.0000 Uiso H271 0.9866 -0.0262 0.1587 0.0464 1.0000 Uiso H272 0.8950 0.1017 0.1816 0.0464 1.0000 Uiso H281 1.1407 0.8394 -0.0763 0.0682 1.0000 Uiso H291 1.3414 -0.2220 0.1865 0.0647 1.0000 Uiso H301 1.3476 0.3475 0.2647 0.0677 1.0000 Uiso H311 1.4733 -0.1256 0.1392 0.0644 1.0000 Uiso H321 1.1943 0.5538 -0.0241 0.0834 1.0000 Uiso H331 1.6006 0.1063 0.1167 0.0866 1.0000 Uiso H332 1.6400 0.2367 0.1668 0.0866 1.0000 Uiso H333 1.5775 0.3589 0.1228 0.0866 1.0000 Uiso H111 1.0955 -0.1144 0.2165 0.0604 1.0000 Uiso 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 0.0563(13) 0.0529(13) 0.0479(11) 0.003(1) -0.003(1) 0.0058(12) O2 0.050(3) 0.020(3) 0.032(3) -0.0073(19) -0.004(2) -0.003(2) N3 0.032(3) 0.025(3) 0.041(3) -0.009(3) -0.011(2) 0.002(3) O4 0.066(4) 0.063(5) 0.070(4) 0.026(4) -0.014(4) -0.005(4) O5 0.036(3) 0.118(7) 0.047(3) -0.008(4) -0.020(3) 0.003(4) C6 0.034(3) 0.022(3) 0.029(3) -0.003(3) -0.003(3) 0.002(3) C7 0.047(4) 0.056(5) 0.026(3) -0.006(4) -0.010(3) 0.017(4) C9 0.044(4) 0.039(4) 0.048(4) 0.003(4) -0.007(3) 0.005(4) C10 0.032(3) 0.043(4) 0.024(3) 0.003(3) -0.005(3) 0.010(3) N11 0.046(4) 0.035(4) 0.072(5) 0.013(4) 0.008(4) -0.001(3) C12 0.037(4) 0.036(4) 0.040(4) 0.000(3) -0.005(3) 0.005(3) C13 0.035(4) 0.033(4) 0.033(3) 0.005(3) 0.007(3) 0.012(3) C14 0.059(5) 0.061(6) 0.037(4) -0.015(4) -0.010(4) 0.022(5) C15 0.058(5) 0.067(6) 0.050(5) 0.005(5) -0.001(4) 0.031(6) C16 0.029(4) 0.072(6) 0.045(4) 0.008(5) -0.000(3) -0.013(4) C17 0.042(5) 0.035(5) 0.081(6) -0.032(5) 0.010(4) -0.009(4) C18 0.037(4) 0.033(4) 0.035(3) 0.006(3) 0.005(3) 0.007(3) C19 0.042(5) 0.086(8) 0.050(5) -0.039(6) 0.007(4) -0.013(5) C20 0.042(5) 0.062(6) 0.056(5) 0.006(5) -0.030(4) -0.013(4) C21 0.042(5) 0.092(8) 0.040(4) 0.014(5) -0.011(3) -0.011(6) C22 0.060(5) 0.055(6) 0.050(5) 0.003(4) -0.007(4) 0.014(5) C23 0.050(5) 0.056(6) 0.037(4) 0.011(4) 0.002(3) -0.002(4) C24 0.056(5) 0.066(7) 0.038(4) 0.004(4) -0.003(4) 0.002(5) C25 0.056(5) 0.053(6) 0.050(5) 0.000(4) -0.018(4) 0.007(5) C26 0.037(4) 0.048(5) 0.039(4) -0.012(4) -0.022(3) 0.011(4) C27 0.043(5) 0.019(4) 0.117(9) 0.005(5) 0.005(5) -0.004(4) C28 0.046(5) 0.086(8) 0.048(5) 0.004(5) -0.005(4) -0.002(5) C29 0.050(5) 0.063(6) 0.043(4) 0.001(4) 0.003(4) -0.021(5) C30 0.088(8) 0.11(1) 0.032(4) -0.025(6) -0.023(5) 0.061(8) C31 0.052(5) 0.044(5) 0.043(4) -0.011(4) -0.014(4) 0.002(4) C32 0.063(6) 0.079(8) 0.059(6) 0.006(6) 0.007(5) 0.031(6) C33 0.054(6) 0.132(12) 0.068(7) 0.044(8) 0.007(5) -0.008(7) O8 0.041(4) 0.058(5) 0.253(14) -0.082(7) -0.056(6) 0.014(4) _refine_ls_extinction_coef 72.977 _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 . O4 . 1.405(8) yes S1 . N11 . 1.628(9) yes S1 . C21 . 1.82(1) yes S1 . O8 . 1.284(9) yes O2 . C6 . 1.230(8) yes N3 . C6 . 1.330(9) yes N3 . C17 . 1.493(11) yes N3 . C26 . 1.45(1) yes O5 . C19 . 1.427(15) yes O5 . C26 . 1.44(1) yes C6 . C18 . 1.52(1) yes C7 . C15 . 1.380(12) yes C7 . C25 . 1.387(13) yes C7 . C26 . 1.520(12) yes C9 . C10 . 1.390(11) yes C9 . C14 . 1.365(12) yes C9 . H91 . 1.016(9) no C10 . C12 . 1.392(11) yes C10 . C13 . 1.50(1) yes N11 . C13 . 1.46(1) yes N11 . H111 . 1.011(8) no C12 . C23 . 1.388(11) yes C12 . H121 . 1.021(8) no C13 . C18 . 1.56(1) yes C13 . H131 . 1.013(8) no C14 . C24 . 1.378(15) yes C14 . H141 . 1.022(9) no C15 . C32 . 1.410(15) yes C15 . H151 . 1.01(1) no C16 . C20 . 1.411(15) yes C16 . C31 . 1.343(13) yes C16 . C33 . 1.515(13) yes C17 . C19 . 1.533(15) yes C17 . C27 . 1.486(17) yes C17 . H171 . 0.994(8) no C18 . C27 . 1.541(13) yes C18 . H181 . 1.002(7) no C19 . H191 . 1.005(9) no C19 . H192 . 1.019(9) no C20 . C30 . 1.426(17) yes C20 . H201 . 1.02(1) no C21 . C29 . 1.296(15) yes C21 . C30 . 1.402(18) yes C22 . C25 . 1.394(15) yes C22 . C28 . 1.392(15) yes C22 . H221 . 1.00(1) no C23 . C24 . 1.364(14) yes C23 . H231 . 1.001(9) no C24 . H241 . 1.003(9) no C25 . H251 . 1.01(1) no C26 . H261 . 1.017(8) no C27 . H271 . 0.988(9) no C27 . H272 . 1.00(1) no C28 . C32 . 1.343(16) yes C28 . H281 . 1.02(1) no C29 . C31 . 1.369(13) yes C29 . H291 . 1.02(1) no C30 . H301 . 1.04(1) no C31 . H311 . 0.998(9) no C32 . H321 . 1.012(11) no C33 . H331 . 1.028(17) no C33 . H332 . 1.010(12) no C33 . H333 . 0.990(14) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O4 . S1 . N11 . 105.8(5) yes O4 . S1 . C21 . 109.6(6) yes N11 . S1 . C21 . 105.4(4) yes O4 . S1 . O8 . 134.6(8) yes N11 . S1 . O8 . 103.6(5) yes C21 . S1 . O8 . 94.9(7) yes C6 . N3 . C17 . 112.2(7) yes C6 . N3 . C26 . 127.8(6) yes C17 . N3 . C26 . 113.4(7) yes C19 . O5 . C26 . 108.1(6) yes O2 . C6 . N3 . 125.3(7) yes O2 . C6 . C18 . 124.9(6) yes N3 . C6 . C18 . 109.7(6) yes C15 . C7 . C25 . 120.0(9) yes C15 . C7 . C26 . 123.0(8) yes C25 . C7 . C26 . 117.0(8) yes C10 . C9 . C14 . 119.1(9) yes C10 . C9 . H91 . 118.8(8) no C14 . C9 . H91 . 122.1(9) no C9 . C10 . C12 . 119.3(7) yes C9 . C10 . C13 . 123.9(8) yes C12 . C10 . C13 . 116.8(7) yes S1 . N11 . C13 . 122.8(6) yes S1 . N11 . H111 . 118.9(6) no C13 . N11 . H111 . 118.3(8) no C10 . C12 . C23 . 119.6(8) yes C10 . C12 . H121 . 119.9(7) no C23 . C12 . H121 . 120.4(8) no C10 . C13 . N11 . 111.9(7) yes C10 . C13 . C18 . 115.1(6) yes N11 . C13 . C18 . 111.8(7) yes C10 . C13 . H131 . 107.4(7) no N11 . C13 . H131 . 106.2(6) no C18 . C13 . H131 . 103.7(6) no C9 . C14 . C24 . 122.4(8) yes C9 . C14 . H141 . 119.4(10) no C24 . C14 . H141 . 118.2(9) no C7 . C15 . C32 . 119.6(9) yes C7 . C15 . H151 . 117.5(9) no C32 . C15 . H151 . 122.5(10) no C20 . C16 . C31 . 118.1(8) yes C20 . C16 . C33 . 118.4(10) yes C31 . C16 . C33 . 123.5(11) yes N3 . C17 . C19 . 95.9(8) yes N3 . C17 . C27 . 105.7(7) yes C19 . C17 . C27 . 122.1(8) yes N3 . C17 . H171 . 124.3(9) no C19 . C17 . H171 . 108.1(9) no C27 . C17 . H171 . 102.5(9) no C6 . C18 . C13 . 108.0(6) yes C6 . C18 . C27 . 103.8(6) yes C13 . C18 . C27 . 116.7(7) yes C6 . C18 . H181 . 119.2(7) no C13 . C18 . H181 . 102.2(6) no C27 . C18 . H181 . 107.6(8) no O5 . C19 . C17 . 107.1(8) yes O5 . C19 . H191 . 111.5(10) no C17 . C19 . H191 . 109.6(9) no O5 . C19 . H192 . 112.2(9) no C17 . C19 . H192 . 108.8(10) no H191 . C19 . H192 . 107.6(9) no C16 . C20 . C30 . 118.0(9) yes C16 . C20 . H201 . 121.0(10) no C30 . C20 . H201 . 121.0(11) no S1 . C21 . C29 . 118.0(9) yes S1 . C21 . C30 . 121.6(9) yes C29 . C21 . C30 . 120.3(9) yes C25 . C22 . C28 . 119.0(9) yes C25 . C22 . H221 . 122.7(10) no C28 . C22 . H221 . 118.3(10) no C12 . C23 . C24 . 121.1(9) yes C12 . C23 . H231 . 120.5(9) no C24 . C23 . H231 . 118.4(8) no C14 . C24 . C23 . 118.4(8) yes C14 . C24 . H241 . 120.6(10) no C23 . C24 . H241 . 121.0(10) no C7 . C25 . C22 . 120.0(9) yes C7 . C25 . H251 . 119.5(10) no C22 . C25 . H251 . 120.4(9) no N3 . C26 . O5 . 103.4(7) yes N3 . C26 . C7 . 112.4(6) yes O5 . C26 . C7 . 107.7(6) yes N3 . C26 . H261 . 111.5(6) no O5 . C26 . H261 . 116.0(7) no C7 . C26 . H261 . 105.9(8) no C17 . C27 . C18 . 105.8(7) yes C17 . C27 . H271 . 109.5(11) no C18 . C27 . H271 . 111.4(9) no C17 . C27 . H272 . 109.6(9) no C18 . C27 . H272 . 110.0(10) no H271 . C27 . H272 . 110.6(9) no C22 . C28 . C32 . 121.5(10) yes C22 . C28 . H281 . 120.7(11) no C32 . C28 . H281 . 117.8(11) no C21 . C29 . C31 . 121.3(10) yes C21 . C29 . H291 . 120.1(9) no C31 . C29 . H291 . 118.5(9) no C20 . C30 . C21 . 119.1(9) yes C20 . C30 . H301 . 120.9(14) no C21 . C30 . H301 . 120.0(14) no C16 . C31 . C29 . 123.0(9) yes C16 . C31 . H311 . 120.1(9) no C29 . C31 . H311 . 116.9(9) no C15 . C32 . C28 . 119.9(10) yes C15 . C32 . H321 . 117.1(11) no C28 . C32 . H321 . 122.9(11) no C16 . C33 . H331 . 109.0(12) no C16 . C33 . H332 . 110.1(9) no H331 . C33 . H332 . 106.5(12) no C16 . C33 . H333 . 113.5(11) no H331 . C33 . H333 . 108.1(10) no H332 . C33 . H333 . 109.5(14) no