Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2003 data_global _publ_contact_author_email rajesh@sil.ncl.res.in _publ_contact_author_name 'Rajesh Gonnade' _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name 'Krishna Ganesh' 'Nagendra K. Sharma' _publ_requested_journal 'Chemical Communications' _publ_section_title ; Expanding the repertoire of pyrrolidyl PNA analogues for DNA/RNA hybridization selectivity: aminoethylpyrrolidinone PNA(aepone-PNA) ; data_3 _database_code_CSD 213533 _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1-(N-Boc-aminoethyl)-4R-O-mesyl-5-one-proline methyl ester' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H24 N2 O8 S' _chemical_formula_sum 'C14 H24 N2 O8 S' _chemical_formula_weight 380.41 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 Monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.739(5) _cell_length_b 9.294(4) _cell_length_c 15.994(6) _cell_angle_alpha 90.00 _cell_angle_beta 103.419(8) _cell_angle_gamma 90.00 _cell_volume 1841.9(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1710 _cell_measurement_theta_min 2.327 _cell_measurement_theta_max 22.512 _exptl_crystal_description 'Thin Plate' _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.61 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.372 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.219 _exptl_absorpt_correction_type Multiscan _exptl_absorpt_correction_T_min 0.8780 _exptl_absorpt_correction_T_max 0.9885 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD Area Detector' _diffrn_measurement_device 'Bruker Smart APEX' _diffrn_measurement_method 'Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9094 _diffrn_reflns_av_R_equivalents 0.0354 _diffrn_reflns_av_sigmaI/netI 0.0708 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6134 _reflns_number_gt 5029 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SAINT' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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^)+(0.0430P)^2^+0.0000P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(9) _refine_ls_number_reflns 6134 _refine_ls_number_parameters 469 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0816 _refine_ls_R_factor_gt 0.0652 _refine_ls_wR_factor_ref 0.1283 _refine_ls_wR_factor_gt 0.1213 _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_restrained_S_all 1.109 _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 0.31709(9) 1.00915(13) 1.17186(7) 0.0431(3) Uani 1 1 d . . . S2 S -0.19179(12) 0.97935(16) 0.67419(8) 0.0588(4) Uani 1 1 d . . . N1 N -0.0993(2) 0.9720(4) 0.3955(2) 0.0364(8) Uani 1 1 d . . . N1' N 0.4204(3) 1.0374(3) 0.9037(2) 0.0342(8) Uani 1 1 d . . . N2' N 0.6349(3) 0.9159(4) 0.8993(3) 0.0463(10) Uani 1 1 d . . . N2 N 0.1212(3) 0.8539(5) 0.4083(2) 0.0469(10) Uani 1 1 d . . . O1 O -0.0315(2) 1.1272(3) 0.50616(19) 0.0564(9) Uani 1 1 d . . . O1' O 0.4734(2) 1.1807(3) 1.02271(18) 0.0541(8) Uani 1 1 d . . . O3 O -0.1197(5) 1.0623(5) 0.7344(3) 0.1213(19) Uani 1 1 d . . . O8 O -0.2937(3) 1.0347(6) 0.6354(3) 0.1063(17) Uani 1 1 d . . . O3' O 0.3847(3) 1.1192(4) 1.2150(2) 0.0762(11) Uani 1 1 d . . . O8' O 0.2068(3) 1.0412(4) 1.1405(2) 0.0681(11) Uani 1 1 d . . . O4' O 0.2339(3) 1.1051(4) 0.7793(2) 0.0659(10) Uani 1 1 d . . . O5' O 0.2115(3) 0.8744(4) 0.7449(2) 0.0666(10) Uani 1 1 d . . . O2' O 0.3653(2) 0.9528(3) 1.09477(17) 0.0517(9) Uani 1 1 d . . . O2 O -0.1305(3) 0.9391(5) 0.60286(19) 0.0749(12) Uani 1 1 d . . . O6 O 0.2585(2) 1.0075(4) 0.40627(19) 0.0599(9) Uani 1 1 d . . . O7 O 0.2722(2) 0.8302(3) 0.50632(18) 0.0501(8) Uani 1 1 d . . . O7' O 0.7835(2) 0.8856(3) 0.99952(18) 0.0508(8) Uani 1 1 d . . . O6' O 0.7631(3) 1.0861(4) 0.9153(2) 0.0696(10) Uani 1 1 d . . . O5 O -0.2609(2) 0.9665(4) 0.2455(2) 0.0578(9) Uani 1 1 d . . . O4 O -0.3677(3) 0.8502(4) 0.3138(2) 0.0710(10) Uani 1 1 d . . . C5' C 0.4160(3) 1.0874(5) 0.9808(2) 0.0383(10) Uani 1 1 d . . . C8' C 0.7314(4) 0.9728(5) 0.9361(3) 0.0433(11) Uani 1 1 d . . . C8 C 0.2205(4) 0.9073(5) 0.4372(3) 0.0426(11) Uani 1 1 d . . . C13 C -0.2793(4) 0.8919(5) 0.3101(3) 0.0450(11) Uani 1 1 d . . . C6 C -0.0284(3) 1.0158(5) 0.3413(2) 0.0413(10) Uani 1 1 d . . . H6A H 0.0118 1.1000 0.3665 0.050 Uiso 1 1 calc R . . H6B H -0.0721 1.0435 0.2856 0.050 Uiso 1 1 calc R . . C5 C -0.0926(3) 1.0310(4) 0.4727(2) 0.0375(10) Uani 1 1 d . . . C9' C 0.8990(3) 0.9090(6) 1.0386(3) 0.0521(12) Uani 1 1 d . . . C2 C -0.1778(3) 0.8542(4) 0.3765(3) 0.0406(10) Uani 1 1 d . . . H2 H -0.1437 0.7708 0.3563 0.049 Uiso 1 1 calc R . . C2' C 0.3409(3) 0.9276(5) 0.8696(3) 0.0400(10) Uani 1 1 d . . . H2' H 0.3772 0.8434 0.8525 0.048 Uiso 1 1 calc R . . C6' C 0.4906(3) 1.0970(5) 0.8524(3) 0.0400(10) Uani 1 1 d . . . H6'A H 0.5347 1.1723 0.8850 0.048 Uiso 1 1 calc R . . H6'B H 0.4466 1.1403 0.8009 0.048 Uiso 1 1 calc R . . C4' C 0.3255(3) 1.0093(5) 1.0095(2) 0.0459(11) Uani 1 1 d . . . H4' H 0.2644 1.0742 1.0079 0.055 Uiso 1 1 calc R . . C15' C 0.3362(4) 0.8547(6) 1.2340(3) 0.0648(14) Uani 1 1 d . . . H15D H 0.4113 0.8294 1.2476 0.097 Uiso 1 1 calc R . . H15E H 0.2948 0.7775 1.2026 0.097 Uiso 1 1 calc R . . H15F H 0.3130 0.8715 1.2861 0.097 Uiso 1 1 calc R . . C7' C 0.5637(3) 0.9848(5) 0.8268(2) 0.0425(10) Uani 1 1 d . . . H7'A H 0.5194 0.9119 0.7920 0.051 Uiso 1 1 calc R . . H7'B H 0.6068 1.0303 0.7916 0.051 Uiso 1 1 calc R . . C9 C 0.3874(3) 0.8538(5) 0.5471(3) 0.0510(12) Uani 1 1 d . . . C13' C 0.2569(3) 0.9812(5) 0.7938(3) 0.0428(10) Uani 1 1 d . . . C7 C 0.0507(3) 0.9010(6) 0.3286(3) 0.0513(12) Uani 1 1 d . . . H7A H 0.0108 0.8188 0.3002 0.062 Uiso 1 1 calc R . . H7B H 0.0943 0.9383 0.2912 0.062 Uiso 1 1 calc R . . C11 C 0.4018(4) 1.0009(6) 0.5887(3) 0.0649(14) Uani 1 1 d . . . H11A H 0.3875 1.0737 0.5450 0.097 Uiso 1 1 calc R . . H11B H 0.4745 1.0107 0.6221 0.097 Uiso 1 1 calc R . . H11C H 0.3525 1.0115 0.6255 0.097 Uiso 1 1 calc R . . C11' C 0.9154(4) 1.0479(6) 1.0883(3) 0.0668(15) Uani 1 1 d . . . H13D H 0.9007 1.1275 1.0491 0.100 Uiso 1 1 calc R . . H13E H 0.9886 1.0534 1.1212 0.100 Uiso 1 1 calc R . . H13F H 0.8673 1.0513 1.1264 0.100 Uiso 1 1 calc R . . C4 C -0.1769(3) 0.9593(5) 0.5123(2) 0.0440(12) Uani 1 1 d . . . H4 H -0.2421 1.0187 0.5037 0.053 Uiso 1 1 calc R . . C3 C -0.2006(4) 0.8189(5) 0.4641(3) 0.0514(12) Uani 1 1 d . . . H3A H -0.2752 0.7903 0.4583 0.062 Uiso 1 1 calc R . . H3B H -0.1537 0.7427 0.4927 0.062 Uiso 1 1 calc R . . C3' C 0.2930(4) 0.8878(5) 0.9462(3) 0.0569(13) Uani 1 1 d . . . H3'A H 0.2151 0.8799 0.9285 0.068 Uiso 1 1 calc R . . H3'B H 0.3222 0.7970 0.9712 0.068 Uiso 1 1 calc R . . C10' C 0.9628(4) 0.9040(7) 0.9692(3) 0.0791(17) Uani 1 1 d . . . H10F H 0.9490 0.8146 0.9385 0.119 Uiso 1 1 calc R . . H10D H 1.0385 0.9116 0.9952 0.119 Uiso 1 1 calc R . . H10E H 0.9413 0.9825 0.9300 0.119 Uiso 1 1 calc R . . C10 C 0.4560(4) 0.8389(7) 0.4815(3) 0.0823(19) Uani 1 1 d . . . H10A H 0.4358 0.7529 0.4484 0.123 Uiso 1 1 calc R . . H10B H 0.5307 0.8335 0.5107 0.123 Uiso 1 1 calc R . . H10C H 0.4447 0.9208 0.4439 0.123 Uiso 1 1 calc R . . C14' C 0.1259(5) 0.9120(7) 0.6712(3) 0.094(2) Uani 1 1 d . . . H14F H 0.0644 0.9459 0.6905 0.140 Uiso 1 1 calc R . . H14E H 0.1060 0.8287 0.6356 0.140 Uiso 1 1 calc R . . H14D H 0.1506 0.9862 0.6387 0.140 Uiso 1 1 calc R . . C14 C -0.3527(4) 0.9984(7) 0.1752(3) 0.0693(15) Uani 1 1 d . . . H14A H -0.3835 0.9101 0.1494 0.104 Uiso 1 1 calc R . . H14B H -0.3294 1.0556 0.1329 0.104 Uiso 1 1 calc R . . H14C H -0.4059 1.0506 0.1967 0.104 Uiso 1 1 calc R . . C15 C -0.2009(6) 0.8116(7) 0.7196(4) 0.103(2) Uani 1 1 d . . . H15A H -0.1302 0.7701 0.7371 0.154 Uiso 1 1 calc R . . H15B H -0.2461 0.7500 0.6781 0.154 Uiso 1 1 calc R . . H15C H -0.2315 0.8218 0.7688 0.154 Uiso 1 1 calc R . . C12' C 0.9259(4) 0.7816(7) 1.0982(4) 0.0833(19) Uani 1 1 d . . . H12E H 0.8854 0.7873 1.1417 0.125 Uiso 1 1 calc R . . H12F H 1.0017 0.7821 1.1248 0.125 Uiso 1 1 calc R . . H12D H 0.9078 0.6943 1.0659 0.125 Uiso 1 1 calc R . . C12 C 0.4104(4) 0.7357(6) 0.6144(4) 0.0822(18) Uani 1 1 d . . . H12A H 0.3588 0.7407 0.6495 0.123 Uiso 1 1 calc R . . H12B H 0.4818 0.7479 0.6498 0.123 Uiso 1 1 calc R . . H12C H 0.4053 0.6436 0.5865 0.123 Uiso 1 1 calc R . . H3 H 0.093(3) 0.786(5) 0.436(2) 0.045(13) Uiso 1 1 d . . . H3' H 0.617(3) 0.841(5) 0.921(3) 0.045(14) 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 S1' 0.0451(6) 0.0456(7) 0.0402(6) -0.0040(5) 0.0135(5) 0.0070(6) S2 0.0772(9) 0.0601(10) 0.0481(7) 0.0026(7) 0.0327(7) -0.0001(7) N1 0.0331(18) 0.044(2) 0.0316(17) -0.0013(16) 0.0069(14) 0.0025(16) N1' 0.0367(18) 0.027(2) 0.0374(18) 0.0005(15) 0.0057(15) -0.0005(15) N2' 0.045(2) 0.036(2) 0.054(2) 0.009(2) 0.0028(19) -0.0045(19) N2 0.035(2) 0.060(3) 0.045(2) 0.013(2) 0.0086(18) 0.0011(19) O1 0.051(2) 0.061(2) 0.0552(18) -0.0230(17) 0.0089(16) -0.0140(17) O1' 0.056(2) 0.057(2) 0.0486(18) -0.0212(16) 0.0115(16) -0.0152(17) O3 0.185(5) 0.099(4) 0.083(3) -0.037(3) 0.038(3) -0.057(3) O8 0.098(3) 0.148(5) 0.089(3) 0.033(3) 0.054(3) 0.061(3) O3' 0.093(3) 0.057(2) 0.077(2) -0.026(2) 0.016(2) -0.009(2) O8' 0.050(2) 0.088(3) 0.069(2) -0.0037(19) 0.0200(17) 0.0216(19) O4' 0.071(2) 0.046(2) 0.068(2) 0.0064(19) -0.0101(18) 0.0035(18) O5' 0.064(2) 0.056(2) 0.064(2) -0.0114(19) -0.0149(18) -0.0137(18) O2' 0.0563(19) 0.065(2) 0.0345(15) 0.0105(14) 0.0123(14) 0.0179(16) O2 0.0451(19) 0.139(4) 0.0400(17) 0.010(2) 0.0087(15) 0.017(2) O6 0.063(2) 0.066(2) 0.0506(18) 0.0208(18) 0.0117(16) -0.0102(19) O7 0.0453(18) 0.053(2) 0.0469(17) 0.0108(15) -0.0005(15) 0.0024(15) O7' 0.0418(17) 0.049(2) 0.0543(18) 0.0165(16) -0.0030(15) -0.0032(15) O6' 0.065(2) 0.061(2) 0.073(2) 0.032(2) -0.0054(18) -0.0182(19) O5 0.0403(17) 0.068(2) 0.0574(18) 0.0222(18) -0.0040(15) -0.0012(16) O4 0.041(2) 0.099(3) 0.068(2) 0.010(2) 0.0019(17) -0.0121(19) C5' 0.036(2) 0.043(3) 0.032(2) 0.002(2) 0.0008(19) 0.012(2) C8' 0.048(3) 0.041(3) 0.042(2) 0.000(2) 0.010(2) 0.004(2) C8 0.049(3) 0.049(3) 0.034(2) 0.001(2) 0.017(2) 0.013(2) C13 0.046(3) 0.042(3) 0.048(3) -0.011(2) 0.010(2) -0.004(2) C6 0.037(2) 0.052(3) 0.034(2) 0.003(2) 0.0056(18) -0.008(2) C5 0.032(2) 0.038(3) 0.039(2) -0.006(2) 0.0028(18) 0.006(2) C9' 0.037(3) 0.065(3) 0.051(3) 0.004(3) 0.002(2) 0.000(2) C2 0.043(2) 0.031(2) 0.048(2) 0.000(2) 0.010(2) -0.0017(19) C2' 0.041(2) 0.034(2) 0.044(2) -0.0038(19) 0.008(2) -0.0026(19) C6' 0.040(2) 0.040(3) 0.040(2) 0.005(2) 0.0088(19) 0.001(2) C4' 0.042(2) 0.057(3) 0.037(2) 0.007(2) 0.0043(19) 0.005(2) C15' 0.080(4) 0.066(4) 0.054(3) 0.003(3) 0.028(3) 0.006(3) C7' 0.041(2) 0.050(3) 0.034(2) 0.007(2) 0.0037(19) -0.002(2) C9 0.040(3) 0.055(3) 0.051(3) -0.002(2) -0.004(2) 0.004(2) C13' 0.044(3) 0.044(3) 0.040(2) -0.001(2) 0.010(2) -0.003(2) C7 0.044(3) 0.072(4) 0.037(2) 0.002(2) 0.008(2) 0.004(2) C11 0.070(3) 0.059(3) 0.060(3) -0.012(3) 0.003(3) 0.004(3) C11' 0.060(3) 0.071(4) 0.065(3) -0.010(3) 0.004(3) -0.003(3) C4 0.032(2) 0.062(3) 0.036(2) 0.006(2) 0.0051(19) 0.007(2) C3 0.052(3) 0.047(3) 0.052(3) 0.015(2) 0.007(2) -0.009(2) C3' 0.062(3) 0.066(3) 0.040(2) 0.000(2) 0.006(2) -0.022(3) C10' 0.064(4) 0.101(5) 0.075(4) -0.002(3) 0.022(3) 0.008(3) C10 0.045(3) 0.111(5) 0.088(4) -0.029(4) 0.008(3) 0.009(3) C14' 0.081(4) 0.107(5) 0.071(4) -0.007(4) -0.026(3) -0.022(4) C14 0.057(3) 0.087(4) 0.055(3) 0.013(3) -0.006(2) -0.005(3) C15 0.151(6) 0.073(5) 0.111(5) 0.011(4) 0.085(5) -0.010(4) C12' 0.054(3) 0.086(4) 0.093(4) 0.030(4) -0.018(3) 0.006(3) C12 0.072(4) 0.067(4) 0.088(4) 0.014(3) -0.022(3) 0.008(3) _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' O8' 1.410(3) . ? S1' O3' 1.410(4) . ? S1' O2' 1.588(3) . ? S1' C15' 1.730(5) . ? S2 O3 1.398(5) . ? S2 O8 1.400(4) . ? S2 O2 1.570(3) . ? S2 C15 1.736(6) . ? N1 C5 1.336(5) . ? N1 C6 1.448(5) . ? N1 C2 1.466(5) . ? N1' C5' 1.331(5) . ? N1' C2' 1.452(5) . ? N1' C6' 1.456(5) . ? N2' C8' 1.342(5) . ? N2' C7' 1.446(5) . ? N2 C8 1.337(6) . ? N2 C7 1.447(5) . ? O1 C5 1.224(5) . ? O1' C5' 1.229(5) . ? O4' C13' 1.197(5) . ? O5' C13' 1.313(5) . ? O5' C14' 1.450(6) . ? O2' C4' 1.440(5) . ? O2 C4 1.443(5) . ? O6 C8 1.207(5) . ? O7 C8 1.353(5) . ? O7 C9 1.477(5) . ? O7' C8' 1.346(5) . ? O7' C9' 1.476(5) . ? O6' C8' 1.202(5) . ? O5 C13 1.310(5) . ? O5 C14 1.453(5) . ? O4 C13 1.206(5) . ? C5' C4' 1.521(6) . ? C13 C2 1.511(6) . ? C6 C7 1.514(6) . ? C5 C4 1.521(6) . ? C9' C11' 1.505(7) . ? C9' C12' 1.509(7) . ? C9' C10' 1.522(6) . ? C2 C3 1.531(5) . ? C2' C13' 1.504(6) . ? C2' C3' 1.534(6) . ? C6' C7' 1.516(6) . ? C4' C3' 1.509(6) . ? C9 C11 1.513(7) . ? C9 C12 1.518(7) . ? C9 C10 1.519(6) . ? C4 C3 1.511(6) . ? 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 O8' S1' O3' 117.8(2) . . ? O8' S1' O2' 109.05(18) . . ? O3' S1' O2' 108.5(2) . . ? O8' S1' C15' 112.0(3) . . ? O3' S1' C15' 109.4(2) . . ? O2' S1' C15' 98.3(2) . . ? O3 S2 O8 119.8(3) . . ? O3 S2 O2 105.9(3) . . ? O8 S2 O2 109.3(2) . . ? O3 S2 C15 107.7(3) . . ? O8 S2 C15 111.7(3) . . ? O2 S2 C15 100.6(3) . . ? C5 N1 C6 121.5(3) . . ? C5 N1 C2 113.1(3) . . ? C6 N1 C2 125.2(3) . . ? C5' N1' C2' 114.6(3) . . ? C5' N1' C6' 123.5(3) . . ? C2' N1' C6' 121.5(3) . . ? C8' N2' C7' 121.2(4) . . ? C8 N2 C7 122.4(4) . . ? C13' O5' C14' 116.5(4) . . ? C4' O2' S1' 120.0(3) . . ? C4 O2 S2 122.8(3) . . ? C8 O7 C9 121.8(4) . . ? C8' O7' C9' 119.9(3) . . ? C13 O5 C14 117.4(4) . . ? O1' C5' N1' 127.2(4) . . ? O1' C5' C4' 124.7(4) . . ? N1' C5' C4' 108.1(4) . . ? O6' C8' N2' 123.7(4) . . ? O6' C8' O7' 126.7(4) . . ? N2' C8' O7' 109.5(4) . . ? O6 C8 N2 125.6(4) . . ? O6 C8 O7 125.3(4) . . ? N2 C8 O7 109.1(4) . . ? O4 C13 O5 123.2(4) . . ? O4 C13 C2 123.2(4) . . ? O5 C13 C2 113.4(4) . . ? N1 C6 C7 114.2(4) . . ? O1 C5 N1 127.0(4) . . ? O1 C5 C4 125.2(4) . . ? N1 C5 C4 107.8(4) . . ? O7' C9' C11' 110.7(4) . . ? O7' C9' C12' 102.1(4) . . ? C11' C9' C12' 110.9(4) . . ? O7' C9' C10' 109.6(4) . . ? C11' C9' C10' 112.3(4) . . ? C12' C9' C10' 110.8(4) . . ? N1 C2 C13 113.8(3) . . ? N1 C2 C3 103.6(3) . . ? C13 C2 C3 112.3(4) . . ? N1' C2' C13' 111.9(3) . . ? N1' C2' C3' 104.0(3) . . ? C13' C2' C3' 112.6(4) . . ? N1' C6' C7' 112.7(3) . . ? O2' C4' C3' 110.1(4) . . ? O2' C4' C5' 109.5(3) . . ? C3' C4' C5' 105.3(3) . . ? N2' C7' C6' 113.5(3) . . ? O7 C9 C11 109.5(4) . . ? O7 C9 C12 102.4(4) . . ? C11 C9 C12 110.9(4) . . ? O7 C9 C10 110.7(3) . . ? C11 C9 C10 110.9(5) . . ? C12 C9 C10 112.1(5) . . ? O4' C13' O5' 123.9(4) . . ? O4' C13' C2' 124.9(4) . . ? O5' C13' C2' 111.3(4) . . ? N2 C7 C6 113.0(3) . . ? O2 C4 C3 112.8(4) . . ? O2 C4 C5 108.1(3) . . ? C3 C4 C5 104.1(3) . . ? C4 C3 C2 102.9(3) . . ? C4' C3' C2' 104.9(3) . . ? 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 O8' S1' O2' C4' 33.7(4) . . . . ? O3' S1' O2' C4' -95.7(4) . . . . ? C15' S1' O2' C4' 150.6(4) . . . . ? O3 S2 O2 C4 -130.2(4) . . . . ? O8 S2 O2 C4 0.1(5) . . . . ? C15 S2 O2 C4 117.8(5) . . . . ? C2' N1' C5' O1' -179.3(4) . . . . ? C6' N1' C5' O1' -5.6(6) . . . . ? C2' N1' C5' C4' 0.2(5) . . . . ? C6' N1' C5' C4' 173.9(3) . . . . ? C7' N2' C8' O6' 3.9(7) . . . . ? C7' N2' C8' O7' -177.5(4) . . . . ? C9' O7' C8' O6' -13.4(7) . . . . ? C9' O7' C8' N2' 168.0(4) . . . . ? C7 N2 C8 O6 7.6(7) . . . . ? C7 N2 C8 O7 -171.9(4) . . . . ? C9 O7 C8 O6 -5.9(6) . . . . ? C9 O7 C8 N2 173.6(3) . . . . ? C14 O5 C13 O4 -0.4(7) . . . . ? C14 O5 C13 C2 175.4(4) . . . . ? C5 N1 C6 C7 112.6(4) . . . . ? C2 N1 C6 C7 -62.3(5) . . . . ? C6 N1 C5 O1 1.9(6) . . . . ? C2 N1 C5 O1 177.3(4) . . . . ? C6 N1 C5 C4 -179.2(3) . . . . ? C2 N1 C5 C4 -3.8(5) . . . . ? C8' O7' C9' C11' 67.5(5) . . . . ? C8' O7' C9' C12' -174.5(4) . . . . ? C8' O7' C9' C10' -57.0(5) . . . . ? C5 N1 C2 C13 107.8(4) . . . . ? C6 N1 C2 C13 -77.0(5) . . . . ? C5 N1 C2 C3 -14.5(4) . . . . ? C6 N1 C2 C3 160.7(4) . . . . ? O4 C13 C2 N1 -142.7(4) . . . . ? O5 C13 C2 N1 41.4(5) . . . . ? O4 C13 C2 C3 -25.4(6) . . . . ? O5 C13 C2 C3 158.8(4) . . . . ? C5' N1' C2' C13' 110.9(4) . . . . ? C6' N1' C2' C13' -62.9(5) . . . . ? C5' N1' C2' C3' -10.8(5) . . . . ? C6' N1' C2' C3' 175.3(4) . . . . ? C5' N1' C6' C7' 124.6(4) . . . . ? C2' N1' C6' C7' -62.1(5) . . . . ? S1' O2' C4' C3' -128.0(3) . . . . ? S1' O2' C4' C5' 116.7(3) . . . . ? O1' C5' C4' O2' -51.3(6) . . . . ? N1' C5' C4' O2' 129.2(4) . . . . ? O1' C5' C4' C3' -169.7(4) . . . . ? N1' C5' C4' C3' 10.8(5) . . . . ? C8' N2' C7' C6' -87.2(5) . . . . ? N1' C6' C7' N2' -60.2(5) . . . . ? C8 O7 C9 C11 67.3(5) . . . . ? C8 O7 C9 C12 -174.9(4) . . . . ? C8 O7 C9 C10 -55.2(6) . . . . ? C14' O5' C13' O4' -2.4(7) . . . . ? C14' O5' C13' C2' 177.7(4) . . . . ? N1' C2' C13' O4' -23.5(6) . . . . ? C3' C2' C13' O4' 93.2(5) . . . . ? N1' C2' C13' O5' 156.4(4) . . . . ? C3' C2' C13' O5' -86.8(4) . . . . ? C8 N2 C7 C6 -96.5(5) . . . . ? N1 C6 C7 N2 -59.4(5) . . . . ? S2 O2 C4 C3 -112.2(4) . . . . ? S2 O2 C4 C5 133.3(4) . . . . ? O1 C5 C4 O2 -40.2(6) . . . . ? N1 C5 C4 O2 140.9(4) . . . . ? O1 C5 C4 C3 -160.3(4) . . . . ? N1 C5 C4 C3 20.8(4) . . . . ? O2 C4 C3 C2 -145.3(3) . . . . ? C5 C4 C3 C2 -28.4(4) . . . . ? N1 C2 C3 C4 26.2(4) . . . . ? C13 C2 C3 C4 -97.1(4) . . . . ? O2' C4' C3' C2' -134.7(4) . . . . ? C5' C4' C3' C2' -16.6(5) . . . . ? N1' C2' C3' C4' 16.6(4) . . . . ? C13' C2' C3' C4' -104.8(4) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.238 _refine_diff_density_min -0.163 _refine_diff_density_rms 0.046