# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Ana I. Jimenez' _publ_contact_author_email anisjim@unizar.es loop_ _publ_author_name P.Fatas A.Jimenez I.M.Calaza C.Cativiela data_Piv-(S,S)-(betaPh)Pro-L-Phe-NHMe_compound_1 _database_code_depnum_ccdc_archive 'CCDC 842881' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '(2S,3S)-N-(tert-butylcarbonyl)-3-phenylprolyl-(S)-N'-methylphenylalaninamide' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H33 N3 O3' _chemical_formula_sum 'C26 H33 N3 O3' _chemical_formula_weight 435.55 _chemical_absolute_configuration syn 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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.7243(3) _cell_length_b 18.0071(8) _cell_length_c 11.1680(5) _cell_angle_alpha 90.00 _cell_angle_beta 96.429(4) _cell_angle_gamma 90.00 _cell_volume 1143.94(9) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Xcalibur, Sapphire3' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11168 _diffrn_reflns_av_R_equivalents 0.0331 _diffrn_reflns_av_sigmaI/netI 0.0634 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4431 _reflns_number_gt 3232 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0272P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0149(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4431 _refine_ls_number_parameters 291 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0543 _refine_ls_R_factor_gt 0.0325 _refine_ls_wR_factor_ref 0.0594 _refine_ls_wR_factor_gt 0.0558 _refine_ls_goodness_of_fit_ref 0.892 _refine_ls_restrained_S_all 0.892 _refine_ls_shift/su_max 0.001 _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 O1 O 1.4005(2) 0.35472(6) 0.64594(10) 0.0269(3) Uani 1 1 d . . . O2 O 1.1150(2) 0.50210(6) 0.74854(10) 0.0244(3) Uani 1 1 d . . . O3 O 0.8818(2) 0.40061(7) 0.97378(11) 0.0289(3) Uani 1 1 d . . . N1 N 1.3866(3) 0.46562(7) 0.55711(12) 0.0229(4) Uani 1 1 d . . . N2 N 1.4235(2) 0.45895(7) 0.87282(11) 0.0192(3) Uani 1 1 d . . . H2 H 1.5817 0.4433 0.8867 0.023 Uiso 1 1 d R . . N3 N 1.0978(2) 0.34527(7) 0.84301(12) 0.0232(3) Uani 1 1 d . . . H3 H 1.2294 0.3510 0.7975 0.028 Uiso 1 1 d R . . C1 C 1.2536(4) 0.27024(10) 0.45702(18) 0.0417(6) Uani 1 1 d . . . H1A H 1.2047 0.2536 0.5340 0.063 Uiso 1 1 calc R . . H1B H 1.4212 0.2597 0.4554 0.063 Uiso 1 1 calc R . . H1C H 1.1622 0.2439 0.3907 0.063 Uiso 1 1 calc R . . C2 C 0.9461(3) 0.36863(11) 0.44426(17) 0.0383(5) Uani 1 1 d . . . H2A H 0.8984 0.3531 0.5220 0.057 Uiso 1 1 calc R . . H2B H 0.8573 0.3403 0.3795 0.057 Uiso 1 1 calc R . . H2C H 0.9139 0.4217 0.4322 0.057 Uiso 1 1 calc R . . C3 C 1.2895(3) 0.37818(10) 0.32168(15) 0.0340(5) Uani 1 1 d . . . H3A H 1.1981 0.3511 0.2562 0.051 Uiso 1 1 calc R . . H3B H 1.4569 0.3671 0.3209 0.051 Uiso 1 1 calc R . . H3C H 1.2637 0.4317 0.3106 0.051 Uiso 1 1 calc R . . C4 C 1.2109(3) 0.35415(10) 0.44281(15) 0.0250(4) Uani 1 1 d . . . C5 C 1.3417(3) 0.39219(10) 0.55415(15) 0.0229(4) Uani 1 1 d . . . C6 C 1.3094(4) 0.52290(9) 0.46665(16) 0.0323(5) Uani 1 1 d . . . H6A H 1.1514 0.5114 0.4254 0.039 Uiso 1 1 calc R . . H6B H 1.4216 0.5274 0.4057 0.039 Uiso 1 1 calc R . . C7 C 1.3053(4) 0.59352(9) 0.54140(15) 0.0300(5) Uani 1 1 d . . . H7A H 1.1547 0.5985 0.5765 0.036 Uiso 1 1 calc R . . H7B H 1.3290 0.6380 0.4921 0.036 Uiso 1 1 calc R . . C8 C 1.5099(3) 0.58285(9) 0.63957(15) 0.0246(4) Uani 1 1 d . . . H8A H 1.6584 0.5896 0.6014 0.030 Uiso 1 1 calc R . . C9 C 1.4905(3) 0.49916(9) 0.67121(13) 0.0217(4) Uani 1 1 d . . . H9A H 1.6492 0.4776 0.6969 0.026 Uiso 1 1 calc R . . C10 C 1.5207(3) 0.63484(9) 0.74674(15) 0.0233(4) Uani 1 1 d . . . C11 C 1.3418(4) 0.68297(11) 0.76520(17) 0.0352(5) Uani 1 1 d . . . H11A H 1.2036 0.6833 0.7095 0.042 Uiso 1 1 calc R . . C12 C 1.3572(4) 0.73104(11) 0.86264(18) 0.0386(5) Uani 1 1 d . . . H12A H 1.2317 0.7641 0.8729 0.046 Uiso 1 1 calc R . . C13 C 1.5559(4) 0.73049(10) 0.94445(17) 0.0355(5) Uani 1 1 d . . . H13A H 1.5685 0.7629 1.0120 0.043 Uiso 1 1 calc R . . C14 C 1.7355(4) 0.68254(11) 0.92707(17) 0.0411(5) Uani 1 1 d . . . H14A H 1.8731 0.6819 0.9832 0.049 Uiso 1 1 calc R . . C15 C 1.7187(4) 0.63526(10) 0.82906(17) 0.0353(5) Uani 1 1 d . . . H15A H 1.8451 0.6027 0.8183 0.042 Uiso 1 1 calc R . . C16 C 1.3266(3) 0.48700(9) 0.76729(14) 0.0200(4) Uani 1 1 d . . . C17 C 1.2806(3) 0.44407(9) 0.96978(14) 0.0204(4) Uani 1 1 d . . . H17A H 1.3800 0.4142 1.0314 0.024 Uiso 1 1 calc R . . C18 C 1.2123(3) 0.51434(10) 1.03250(15) 0.0264(4) Uani 1 1 d . . . H18A H 1.1586 0.5514 0.9699 0.032 Uiso 1 1 calc R . . H18B H 1.0765 0.5027 1.0769 0.032 Uiso 1 1 calc R . . C19 C 1.4012(3) 0.55005(9) 1.11987(14) 0.0207(4) Uani 1 1 d . . . C20 C 1.6194(3) 0.51842(10) 1.15295(15) 0.0253(4) Uani 1 1 d . . . H20A H 1.6583 0.4724 1.1188 0.030 Uiso 1 1 calc R . . C21 C 1.7813(3) 0.55349(10) 1.23549(15) 0.0281(4) Uani 1 1 d . . . H21A H 1.9296 0.5309 1.2582 0.034 Uiso 1 1 calc R . . C22 C 1.7299(4) 0.62083(10) 1.28516(16) 0.0300(5) Uani 1 1 d . . . H22A H 1.8421 0.6443 1.3419 0.036 Uiso 1 1 calc R . . C23 C 1.5158(3) 0.65387(10) 1.25224(16) 0.0289(5) Uani 1 1 d . . . H23A H 1.4791 0.7005 1.2854 0.035 Uiso 1 1 calc R . . C24 C 1.3540(3) 0.61824(9) 1.16992(15) 0.0245(4) Uani 1 1 d . . . H24A H 1.2063 0.6412 1.1471 0.029 Uiso 1 1 calc R . . C25 C 1.0668(3) 0.39626(9) 0.92650(15) 0.0212(4) Uani 1 1 d . . . C26 C 0.9081(3) 0.29648(10) 0.79675(17) 0.0317(5) Uani 1 1 d . . . H26A H 0.8347 0.2751 0.8641 0.048 Uiso 1 1 calc R . . H26B H 0.9704 0.2565 0.7500 0.048 Uiso 1 1 calc R . . H26C H 0.7907 0.3248 0.7448 0.048 Uiso 1 1 calc 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 O1 0.0319(8) 0.0272(7) 0.0211(7) 0.0005(6) 0.0005(6) 0.0046(6) O2 0.0206(7) 0.0293(7) 0.0226(6) 0.0018(5) -0.0009(6) 0.0014(6) O3 0.0216(7) 0.0327(7) 0.0331(7) -0.0019(6) 0.0058(6) -0.0001(6) N1 0.0263(9) 0.0248(9) 0.0169(7) -0.0006(6) -0.0006(7) 0.0012(7) N2 0.0152(8) 0.0237(8) 0.0182(7) 0.0006(6) -0.0007(7) 0.0042(7) N3 0.0205(9) 0.0220(8) 0.0272(8) -0.0011(7) 0.0027(7) -0.0012(7) C1 0.0575(17) 0.0277(11) 0.0367(12) -0.0090(9) -0.0094(11) -0.0009(10) C2 0.0322(12) 0.0465(13) 0.0348(11) -0.0022(10) -0.0019(10) -0.0057(10) C3 0.0347(12) 0.0465(13) 0.0204(10) -0.0062(9) 0.0012(9) 0.0013(10) C4 0.0243(10) 0.0265(10) 0.0234(10) -0.0012(8) -0.0013(8) 0.0003(9) C5 0.0200(10) 0.0262(11) 0.0234(10) -0.0013(8) 0.0060(8) 0.0032(9) C6 0.0433(13) 0.0294(11) 0.0229(10) 0.0051(8) -0.0015(9) -0.0035(10) C7 0.0393(12) 0.0258(10) 0.0237(10) 0.0036(8) -0.0014(10) -0.0031(10) C8 0.0257(11) 0.0256(10) 0.0223(10) 0.0003(8) 0.0021(8) -0.0055(9) C9 0.0196(10) 0.0257(9) 0.0188(9) -0.0023(8) -0.0019(8) -0.0006(8) C10 0.0241(11) 0.0223(10) 0.0235(10) 0.0044(8) 0.0027(9) -0.0049(9) C11 0.0296(12) 0.0373(12) 0.0369(11) -0.0062(9) -0.0041(10) 0.0011(10) C12 0.0397(13) 0.0350(12) 0.0414(13) -0.0080(10) 0.0068(11) 0.0026(11) C13 0.0502(15) 0.0263(11) 0.0300(11) -0.0061(9) 0.0042(11) -0.0099(11) C14 0.0396(13) 0.0457(13) 0.0343(12) -0.0053(10) -0.0123(10) -0.0029(12) C15 0.0328(12) 0.0351(12) 0.0363(11) -0.0019(9) -0.0041(10) 0.0041(10) C16 0.0225(11) 0.0143(9) 0.0219(9) -0.0056(7) -0.0037(8) -0.0011(8) C17 0.0181(10) 0.0261(10) 0.0164(9) 0.0025(7) -0.0002(8) 0.0027(8) C18 0.0222(10) 0.0325(11) 0.0243(10) -0.0065(8) 0.0022(8) 0.0052(9) C19 0.0208(10) 0.0248(10) 0.0172(9) 0.0017(7) 0.0047(8) -0.0012(8) C20 0.0262(11) 0.0289(11) 0.0209(9) -0.0049(8) 0.0036(8) 0.0050(9) C21 0.0223(11) 0.0390(11) 0.0225(10) -0.0029(8) 0.0001(9) 0.0031(10) C22 0.0314(12) 0.0348(11) 0.0229(10) -0.0033(8) -0.0009(9) -0.0079(10) C23 0.0347(12) 0.0239(10) 0.0276(10) -0.0035(8) 0.0006(10) -0.0013(9) C24 0.0250(11) 0.0233(10) 0.0247(10) 0.0031(8) 0.0012(9) 0.0041(9) C25 0.0189(10) 0.0224(9) 0.0218(9) 0.0040(8) 0.0006(8) 0.0025(9) C26 0.0295(12) 0.0284(11) 0.0364(11) -0.0034(8) -0.0002(10) -0.0047(10) _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 O1 C5 1.2419(19) . ? O2 C16 1.236(2) . ? O3 C25 1.238(2) . ? N1 C5 1.347(2) . ? N1 C9 1.474(2) . ? N1 C6 1.476(2) . ? N2 C16 1.344(2) . ? N2 C17 1.453(2) . ? N2 H2 0.9448 . ? N3 C25 1.335(2) . ? N3 C26 1.446(2) . ? N3 H3 0.9603 . ? C1 C4 1.536(2) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C4 1.540(2) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.535(2) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C5 1.538(2) . ? C6 C7 1.523(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.524(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C10 1.515(2) . ? C8 C9 1.555(2) . ? C8 H8A 1.0000 . ? C9 C16 1.518(2) . ? C9 H9A 1.0000 . ? C10 C11 1.375(3) . ? C10 C15 1.377(3) . ? C11 C12 1.386(3) . ? C11 H11A 0.9500 . ? C12 C13 1.377(3) . ? C12 H12A 0.9500 . ? C13 C14 1.373(3) . ? C13 H13A 0.9500 . ? C14 C15 1.381(3) . ? C14 H14A 0.9500 . ? C15 H15A 0.9500 . ? C17 C18 1.518(2) . ? C17 C25 1.529(2) . ? C17 H17A 1.0000 . ? C18 C19 1.516(2) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.385(2) . ? C19 C24 1.388(2) . ? C20 C21 1.384(2) . ? C20 H20A 0.9500 . ? C21 C22 1.379(2) . ? C21 H21A 0.9500 . ? C22 C23 1.375(3) . ? C22 H22A 0.9500 . ? C23 C24 1.387(2) . ? C23 H23A 0.9500 . ? C24 H24A 0.9500 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? 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 C5 N1 C9 118.75(13) . . ? C5 N1 C6 128.87(13) . . ? C9 N1 C6 111.48(13) . . ? C16 N2 C17 120.76(14) . . ? C16 N2 H2 123.4 . . ? C17 N2 H2 115.6 . . ? C25 N3 C26 120.96(15) . . ? C25 N3 H3 118.0 . . ? C26 N3 H3 118.5 . . ? C4 C1 H1A 109.5 . . ? C4 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C4 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C4 C2 H2A 109.5 . . ? C4 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C4 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C4 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C3 C4 C1 108.02(15) . . ? C3 C4 C5 115.02(15) . . ? C1 C4 C5 107.29(14) . . ? C3 C4 C2 110.33(15) . . ? C1 C4 C2 108.10(17) . . ? C5 C4 C2 107.85(14) . . ? O1 C5 N1 118.67(15) . . ? O1 C5 C4 119.19(16) . . ? N1 C5 C4 122.08(14) . . ? N1 C6 C7 103.30(13) . . ? N1 C6 H6A 111.1 . . ? C7 C6 H6A 111.1 . . ? N1 C6 H6B 111.1 . . ? C7 C6 H6B 111.1 . . ? H6A C6 H6B 109.1 . . ? C6 C7 C8 103.38(15) . . ? C6 C7 H7A 111.1 . . ? C8 C7 H7A 111.1 . . ? C6 C7 H7B 111.1 . . ? C8 C7 H7B 111.1 . . ? H7A C7 H7B 109.1 . . ? C10 C8 C7 116.79(15) . . ? C10 C8 C9 114.64(14) . . ? C7 C8 C9 102.53(13) . . ? C10 C8 H8A 107.4 . . ? C7 C8 H8A 107.4 . . ? C9 C8 H8A 107.4 . . ? N1 C9 C16 109.30(13) . . ? N1 C9 C8 103.46(13) . . ? C16 C9 C8 111.47(14) . . ? N1 C9 H9A 110.8 . . ? C16 C9 H9A 110.8 . . ? C8 C9 H9A 110.8 . . ? C11 C10 C15 117.87(17) . . ? C11 C10 C8 122.85(16) . . ? C15 C10 C8 119.27(17) . . ? C10 C11 C12 121.92(18) . . ? C10 C11 H11A 119.0 . . ? C12 C11 H11A 119.0 . . ? C13 C12 C11 119.5(2) . . ? C13 C12 H12A 120.3 . . ? C11 C12 H12A 120.3 . . ? C14 C13 C12 119.12(18) . . ? C14 C13 H13A 120.4 . . ? C12 C13 H13A 120.4 . . ? C13 C14 C15 120.84(18) . . ? C13 C14 H14A 119.6 . . ? C15 C14 H14A 119.6 . . ? C10 C15 C14 120.77(19) . . ? C10 C15 H15A 119.6 . . ? C14 C15 H15A 119.6 . . ? O2 C16 N2 122.11(16) . . ? O2 C16 C9 121.32(15) . . ? N2 C16 C9 116.57(15) . . ? N2 C17 C18 112.68(14) . . ? N2 C17 C25 111.43(13) . . ? C18 C17 C25 112.13(14) . . ? N2 C17 H17A 106.7 . . ? C18 C17 H17A 106.7 . . ? C25 C17 H17A 106.7 . . ? C19 C18 C17 116.64(14) . . ? C19 C18 H18A 108.1 . . ? C17 C18 H18A 108.1 . . ? C19 C18 H18B 108.1 . . ? C17 C18 H18B 108.1 . . ? H18A C18 H18B 107.3 . . ? C20 C19 C24 117.83(16) . . ? C20 C19 C18 123.66(15) . . ? C24 C19 C18 118.52(16) . . ? C21 C20 C19 120.44(16) . . ? C21 C20 H20A 119.8 . . ? C19 C20 H20A 119.8 . . ? C22 C21 C20 120.80(18) . . ? C22 C21 H21A 119.6 . . ? C20 C21 H21A 119.6 . . ? C23 C22 C21 119.79(18) . . ? C23 C22 H22A 120.1 . . ? C21 C22 H22A 120.1 . . ? C22 C23 C24 119.09(17) . . ? C22 C23 H23A 120.5 . . ? C24 C23 H23A 120.5 . . ? C23 C24 C19 122.03(17) . . ? C23 C24 H24A 119.0 . . ? C19 C24 H24A 119.0 . . ? O3 C25 N3 121.90(16) . . ? O3 C25 C17 121.47(15) . . ? N3 C25 C17 116.37(15) . . ? N3 C26 H26A 109.5 . . ? N3 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N3 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 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 C9 N1 C5 O1 -3.7(2) . . . . ? C6 N1 C5 O1 -171.75(17) . . . . ? C9 N1 C5 C4 173.70(15) . . . . ? C6 N1 C5 C4 5.6(3) . . . . ? C3 C4 C5 O1 -138.80(16) . . . . ? C1 C4 C5 O1 -18.6(2) . . . . ? C2 C4 C5 O1 97.62(18) . . . . ? C3 C4 C5 N1 43.9(2) . . . . ? C1 C4 C5 N1 164.04(17) . . . . ? C2 C4 C5 N1 -79.7(2) . . . . ? C5 N1 C6 C7 152.87(17) . . . . ? C9 N1 C6 C7 -15.9(2) . . . . ? N1 C6 C7 C8 34.48(19) . . . . ? C6 C7 C8 C10 -166.06(15) . . . . ? C6 C7 C8 C9 -39.84(18) . . . . ? C5 N1 C9 C16 -59.93(19) . . . . ? C6 N1 C9 C16 110.13(16) . . . . ? C5 N1 C9 C8 -178.79(15) . . . . ? C6 N1 C9 C8 -8.73(19) . . . . ? C10 C8 C9 N1 157.37(15) . . . . ? C7 C8 C9 N1 29.78(17) . . . . ? C10 C8 C9 C16 40.0(2) . . . . ? C7 C8 C9 C16 -87.57(16) . . . . ? C7 C8 C10 C11 8.6(3) . . . . ? C9 C8 C10 C11 -111.3(2) . . . . ? C7 C8 C10 C15 -170.42(17) . . . . ? C9 C8 C10 C15 69.6(2) . . . . ? C15 C10 C11 C12 0.3(3) . . . . ? C8 C10 C11 C12 -178.77(18) . . . . ? C10 C11 C12 C13 -0.6(3) . . . . ? C11 C12 C13 C14 0.5(3) . . . . ? C12 C13 C14 C15 0.0(3) . . . . ? C11 C10 C15 C14 0.2(3) . . . . ? C8 C10 C15 C14 179.28(17) . . . . ? C13 C14 C15 C10 -0.3(3) . . . . ? C17 N2 C16 O2 0.9(2) . . . . ? C17 N2 C16 C9 -178.92(14) . . . . ? N1 C9 C16 O2 -49.7(2) . . . . ? C8 C9 C16 O2 64.01(19) . . . . ? N1 C9 C16 N2 130.07(15) . . . . ? C8 C9 C16 N2 -116.17(16) . . . . ? C16 N2 C17 C18 -74.78(18) . . . . ? C16 N2 C17 C25 52.3(2) . . . . ? N2 C17 C18 C19 -76.54(18) . . . . ? C25 C17 C18 C19 156.77(15) . . . . ? C17 C18 C19 C20 -6.4(2) . . . . ? C17 C18 C19 C24 173.60(15) . . . . ? C24 C19 C20 C21 1.5(2) . . . . ? C18 C19 C20 C21 -178.48(18) . . . . ? C19 C20 C21 C22 -0.8(3) . . . . ? C20 C21 C22 C23 -0.2(3) . . . . ? C21 C22 C23 C24 0.5(3) . . . . ? C22 C23 C24 C19 0.2(3) . . . . ? C20 C19 C24 C23 -1.2(3) . . . . ? C18 C19 C24 C23 178.77(17) . . . . ? C26 N3 C25 O3 5.1(2) . . . . ? C26 N3 C25 C17 179.29(15) . . . . ? N2 C17 C25 O3 -151.15(15) . . . . ? C18 C17 C25 O3 -23.8(2) . . . . ? N2 C17 C25 N3 34.68(19) . . . . ? C18 C17 C25 N3 162.03(15) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3 O1 0.96 2.05 2.9547(18) 156.4 . N2 H2 O3 0.94 2.03 2.9320(17) 159.5 1_655 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.155 _refine_diff_density_min -0.142 _refine_diff_density_rms 0.031 # Attachment '2.cif' data_Piv-(S,S)-(betaPh)Pro-D-Phe-NHMe_compound_2 _database_code_depnum_ccdc_archive 'CCDC 842882' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '(2S,3S)-N-(tert-butylcarbonyl)-3-phenylprolyl-(R)-N'-methylphenylalaninamide' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H33 N3 O3' _chemical_formula_sum 'C26 H33 N3 O3' _chemical_formula_weight 435.55 _chemical_absolute_configuration syn 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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.7726(6) _cell_length_b 17.590(2) _cell_length_c 11.5824(14) _cell_angle_alpha 90.00 _cell_angle_beta 96.205(10) _cell_angle_gamma 90.00 _cell_volume 1169.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.237 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Xcalibur, Sapphire3' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20298 _diffrn_reflns_av_R_equivalents 0.1037 _diffrn_reflns_av_sigmaI/netI 0.1384 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 25.04 _reflns_number_total 4111 _reflns_number_gt 2339 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0415P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4111 _refine_ls_number_parameters 290 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1006 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.0966 _refine_ls_wR_factor_gt 0.0871 _refine_ls_goodness_of_fit_ref 0.860 _refine_ls_restrained_S_all 0.860 _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 O1 O 0.1341(4) 0.20209(14) 0.82087(19) 0.0323(6) Uani 1 1 d . . . O2 O 0.4401(4) 0.36042(13) 0.77037(18) 0.0309(6) Uani 1 1 d . . . O3 O 0.7288(4) 0.25516(13) 0.54871(18) 0.0336(7) Uani 1 1 d . . . N1 N 0.1197(4) 0.31011(15) 0.9210(2) 0.0244(7) Uani 1 1 d . . . N2 N 0.1782(4) 0.32543(15) 0.6217(2) 0.0240(7) Uani 1 1 d . . . H2 H 0.0103 0.3116 0.5897 0.029 Uiso 1 1 d R . . N3 N 0.4602(4) 0.19854(16) 0.6468(2) 0.0285(7) Uani 1 1 d . . . H3 H 0.3032 0.2031 0.6850 0.034 Uiso 1 1 d R . . C1 C 0.5450(5) 0.2090(2) 1.0328(3) 0.0452(10) Uani 1 1 d . . . H1A H 0.5711 0.2629 1.0516 0.068 Uiso 1 1 calc R . . H1B H 0.6073 0.1974 0.9594 0.068 Uiso 1 1 calc R . . H1C H 0.6242 0.1776 1.0949 0.068 Uiso 1 1 calc R . . C2 C 0.2477(7) 0.1072(2) 0.9971(3) 0.0577(12) Uani 1 1 d . . . H2A H 0.3097 0.0941 0.9242 0.087 Uiso 1 1 calc R . . H2B H 0.0811 0.0952 0.9910 0.087 Uiso 1 1 calc R . . H2C H 0.3300 0.0779 1.0609 0.087 Uiso 1 1 calc R . . C3 C 0.1907(6) 0.2088(2) 1.1365(3) 0.0480(11) Uani 1 1 d . . . H3A H 0.2474 0.2586 1.1651 0.072 Uiso 1 1 calc R . . H3B H 0.2453 0.1696 1.1931 0.072 Uiso 1 1 calc R . . H3C H 0.0199 0.2091 1.1260 0.072 Uiso 1 1 calc R . . C4 C 0.2828(6) 0.1921(2) 1.0210(3) 0.0302(9) Uani 1 1 d . . . C5 C 0.1699(5) 0.2358(2) 0.9164(3) 0.0219(8) Uani 1 1 d . . . C6 C 0.1712(6) 0.3644(2) 1.0162(3) 0.0382(10) Uani 1 1 d . . . H6A H 0.3242 0.3534 1.0603 0.046 Uiso 1 1 calc R . . H6B H 0.0493 0.3630 1.0701 0.046 Uiso 1 1 calc R . . C7 C 0.1740(6) 0.4402(2) 0.9559(3) 0.0381(10) Uani 1 1 d . . . H7A H 0.3312 0.4517 0.9339 0.046 Uiso 1 1 calc R . . H7B H 0.1260 0.4814 1.0064 0.046 Uiso 1 1 calc R . . C8 C -0.0011(6) 0.4310(2) 0.8486(3) 0.0297(9) Uani 1 1 d . . . H8A H -0.1599 0.4319 0.8756 0.036 Uiso 1 1 calc R . . C9 C 0.0438(5) 0.34895(19) 0.8107(3) 0.0266(8) Uani 1 1 d . . . H9A H -0.1023 0.3255 0.7721 0.032 Uiso 1 1 calc R . . C10 C -0.0011(6) 0.48900(19) 0.7527(3) 0.0303(9) Uani 1 1 d . . . C11 C -0.1958(6) 0.4961(2) 0.6722(3) 0.0401(10) Uani 1 1 d . . . H11A H -0.3291 0.4658 0.6809 0.048 Uiso 1 1 calc R . . C12 C -0.2015(7) 0.5458(2) 0.5801(3) 0.0486(12) Uani 1 1 d . . . H12A H -0.3357 0.5488 0.5251 0.058 Uiso 1 1 calc R . . C13 C -0.0093(7) 0.5916(2) 0.5683(3) 0.0443(11) Uani 1 1 d . . . H13A H -0.0106 0.6261 0.5052 0.053 Uiso 1 1 calc R . . C14 C 0.1809(7) 0.5862(2) 0.6483(4) 0.0472(11) Uani 1 1 d . . . H14A H 0.3116 0.6180 0.6412 0.057 Uiso 1 1 calc R . . C15 C 0.1873(6) 0.5359(2) 0.7389(3) 0.0401(10) Uani 1 1 d . . . H15A H 0.3228 0.5330 0.7931 0.048 Uiso 1 1 calc R . . C16 C 0.2378(6) 0.34522(19) 0.7321(3) 0.0248(8) Uani 1 1 d . . . C17 C 0.3578(6) 0.31710(19) 0.5443(2) 0.0256(9) Uani 1 1 d . . . H17A H 0.4429 0.3665 0.5415 0.031 Uiso 1 1 calc R . . C18 C 0.2526(6) 0.29700(18) 0.4220(3) 0.0281(9) Uani 1 1 d . . . H18A H 0.3817 0.2896 0.3733 0.034 Uiso 1 1 calc R . . H18B H 0.1710 0.2477 0.4253 0.034 Uiso 1 1 calc R . . C19 C 0.0830(6) 0.35411(19) 0.3615(3) 0.0244(8) Uani 1 1 d . . . C20 C 0.1411(6) 0.4288(2) 0.3467(3) 0.0354(9) Uani 1 1 d . . . H20A H 0.2898 0.4465 0.3786 0.042 Uiso 1 1 calc R . . C21 C -0.0125(7) 0.4788(2) 0.2861(3) 0.0410(10) Uani 1 1 d . . . H21A H 0.0332 0.5300 0.2755 0.049 Uiso 1 1 calc R . . C22 C -0.2297(6) 0.4550(2) 0.2413(3) 0.0355(10) Uani 1 1 d . . . H22A H -0.3365 0.4892 0.2005 0.043 Uiso 1 1 calc R . . C23 C -0.2886(6) 0.3805(2) 0.2571(3) 0.0385(10) Uani 1 1 d . . . H23A H -0.4385 0.3630 0.2265 0.046 Uiso 1 1 calc R . . C24 C -0.1364(6) 0.3306(2) 0.3161(3) 0.0303(9) Uani 1 1 d . . . H24A H -0.1822 0.2793 0.3259 0.036 Uiso 1 1 calc R . . C25 C 0.5337(6) 0.25479(19) 0.5824(3) 0.0291(9) Uani 1 1 d . . . C26 C 0.6137(6) 0.1363(2) 0.6860(3) 0.0360(10) Uani 1 1 d . . . H26A H 0.7548 0.1566 0.7300 0.054 Uiso 1 1 calc R . . H26B H 0.6564 0.1079 0.6186 0.054 Uiso 1 1 calc R . . H26C H 0.5337 0.1024 0.7358 0.054 Uiso 1 1 calc 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 O1 0.0323(14) 0.0369(16) 0.0285(15) -0.0022(12) 0.0074(11) -0.0056(13) O2 0.0177(13) 0.0394(17) 0.0358(14) -0.0012(12) 0.0040(10) -0.0017(12) O3 0.0175(14) 0.0468(19) 0.0379(14) 0.0027(12) 0.0092(11) 0.0020(12) N1 0.0240(16) 0.0271(19) 0.0224(16) -0.0050(13) 0.0037(12) 0.0013(14) N2 0.0156(15) 0.0346(19) 0.0222(16) -0.0028(13) 0.0036(12) 0.0022(13) N3 0.0246(16) 0.0230(18) 0.0387(17) 0.0056(15) 0.0071(13) 0.0039(15) C1 0.036(2) 0.057(3) 0.042(2) 0.010(2) 0.0026(18) 0.011(2) C2 0.079(3) 0.041(3) 0.051(3) 0.011(2) -0.002(2) -0.004(2) C3 0.048(3) 0.051(3) 0.045(3) 0.006(2) 0.005(2) 0.004(2) C4 0.031(2) 0.031(3) 0.029(2) -0.0003(17) 0.0051(16) 0.0001(18) C5 0.0135(19) 0.033(2) 0.0194(19) -0.0034(17) 0.0050(15) -0.0079(16) C6 0.035(2) 0.039(3) 0.041(2) -0.0077(19) 0.0034(18) 0.012(2) C7 0.053(3) 0.029(2) 0.032(2) -0.0065(18) 0.0008(18) 0.013(2) C8 0.029(2) 0.030(2) 0.030(2) -0.0009(18) 0.0047(16) 0.0056(18) C9 0.0137(18) 0.040(2) 0.0265(19) 0.0009(18) 0.0050(14) -0.0044(17) C10 0.027(2) 0.027(2) 0.037(2) -0.0060(18) 0.0064(18) 0.0125(19) C11 0.029(2) 0.045(3) 0.047(3) 0.006(2) 0.0052(19) 0.002(2) C12 0.038(3) 0.064(3) 0.043(3) 0.012(2) 0.0004(19) 0.008(2) C13 0.053(3) 0.035(3) 0.047(3) 0.007(2) 0.016(2) 0.013(2) C14 0.051(3) 0.037(3) 0.055(3) 0.003(2) 0.012(2) -0.002(2) C15 0.029(2) 0.043(3) 0.048(3) 0.002(2) 0.0021(18) -0.002(2) C16 0.019(2) 0.023(2) 0.033(2) 0.0028(17) 0.0031(16) -0.0002(17) C17 0.025(2) 0.025(2) 0.028(2) -0.0024(16) 0.0072(16) 0.0005(17) C18 0.028(2) 0.027(2) 0.0279(19) 0.0004(16) -0.0006(16) -0.0041(17) C19 0.025(2) 0.023(2) 0.0259(19) -0.0008(16) 0.0055(15) -0.0013(18) C20 0.032(2) 0.030(3) 0.043(2) -0.0016(19) -0.0016(18) -0.008(2) C21 0.046(3) 0.022(2) 0.054(3) 0.0070(19) 0.003(2) -0.003(2) C22 0.028(2) 0.037(3) 0.041(2) 0.0033(19) 0.0021(18) 0.007(2) C23 0.027(2) 0.054(3) 0.032(2) 0.002(2) -0.0061(17) -0.005(2) C24 0.034(2) 0.031(2) 0.0260(19) 0.0001(18) 0.0027(17) -0.006(2) C25 0.034(2) 0.031(3) 0.0226(19) -0.0028(17) 0.0016(18) 0.006(2) C26 0.028(2) 0.042(3) 0.038(2) 0.0028(19) 0.0026(17) 0.004(2) _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 O1 C5 1.253(4) . ? O2 C16 1.233(4) . ? O3 C25 1.231(4) . ? N1 C5 1.341(4) . ? N1 C6 1.465(4) . ? N1 C9 1.473(4) . ? N2 C16 1.334(4) . ? N2 C17 1.449(4) . ? N2 H2 1.0289 . ? N3 C25 1.336(4) . ? N3 C26 1.450(4) . ? N3 H3 1.0538 . ? C1 C4 1.534(4) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C4 1.528(5) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.521(4) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C5 1.520(4) . ? C6 C7 1.505(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.524(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C10 1.508(4) . ? C8 C9 1.538(5) . ? C8 H8A 1.0000 . ? C9 C16 1.519(4) . ? C9 H9A 1.0000 . ? C10 C11 1.386(4) . ? C10 C15 1.387(4) . ? C11 C12 1.377(5) . ? C11 H11A 0.9500 . ? C12 C13 1.389(5) . ? C12 H12A 0.9500 . ? C13 C14 1.361(5) . ? C13 H13A 0.9500 . ? C14 C15 1.371(5) . ? C14 H14A 0.9500 . ? C15 H15A 0.9500 . ? C17 C18 1.521(4) . ? C17 C25 1.526(4) . ? C17 H17A 1.0000 . ? C18 C19 1.520(4) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.371(4) . ? C19 C24 1.381(4) . ? C20 C21 1.385(5) . ? C20 H20A 0.9500 . ? C21 C22 1.369(4) . ? C21 H21A 0.9500 . ? C22 C23 1.372(5) . ? C22 H22A 0.9500 . ? C23 C24 1.371(4) . ? C23 H23A 0.9500 . ? C24 H24A 0.9500 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? 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 C5 N1 C6 129.7(3) . . ? C5 N1 C9 117.6(3) . . ? C6 N1 C9 111.6(3) . . ? C16 N2 C17 119.4(3) . . ? C16 N2 H2 122.8 . . ? C17 N2 H2 117.6 . . ? C25 N3 C26 120.9(3) . . ? C25 N3 H3 121.2 . . ? C26 N3 H3 116.7 . . ? C4 C1 H1A 109.5 . . ? C4 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C4 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C4 C2 H2A 109.5 . . ? C4 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C4 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C4 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C5 C4 C3 116.3(3) . . ? C5 C4 C2 108.2(3) . . ? C3 C4 C2 107.2(3) . . ? C5 C4 C1 107.9(3) . . ? C3 C4 C1 108.7(3) . . ? C2 C4 C1 108.4(3) . . ? O1 C5 N1 118.7(3) . . ? O1 C5 C4 118.7(3) . . ? N1 C5 C4 122.5(3) . . ? N1 C6 C7 103.9(3) . . ? N1 C6 H6A 111.0 . . ? C7 C6 H6A 111.0 . . ? N1 C6 H6B 111.0 . . ? C7 C6 H6B 111.0 . . ? H6A C6 H6B 109.0 . . ? C6 C7 C8 104.2(3) . . ? C6 C7 H7A 110.9 . . ? C8 C7 H7A 110.9 . . ? C6 C7 H7B 110.9 . . ? C8 C7 H7B 110.9 . . ? H7A C7 H7B 108.9 . . ? C10 C8 C7 118.4(3) . . ? C10 C8 C9 114.3(3) . . ? C7 C8 C9 102.4(3) . . ? C10 C8 H8A 107.0 . . ? C7 C8 H8A 107.0 . . ? C9 C8 H8A 107.0 . . ? N1 C9 C16 109.3(2) . . ? N1 C9 C8 103.4(2) . . ? C16 C9 C8 111.7(3) . . ? N1 C9 H9A 110.8 . . ? C16 C9 H9A 110.8 . . ? C8 C9 H9A 110.8 . . ? C11 C10 C15 117.3(3) . . ? C11 C10 C8 119.4(3) . . ? C15 C10 C8 123.3(3) . . ? C12 C11 C10 121.9(4) . . ? C12 C11 H11A 119.1 . . ? C10 C11 H11A 119.1 . . ? C11 C12 C13 119.4(3) . . ? C11 C12 H12A 120.3 . . ? C13 C12 H12A 120.3 . . ? C14 C13 C12 119.2(4) . . ? C14 C13 H13A 120.4 . . ? C12 C13 H13A 120.4 . . ? C13 C14 C15 121.2(4) . . ? C13 C14 H14A 119.4 . . ? C15 C14 H14A 119.4 . . ? C14 C15 C10 121.0(3) . . ? C14 C15 H15A 119.5 . . ? C10 C15 H15A 119.5 . . ? O2 C16 N2 122.5(3) . . ? O2 C16 C9 120.4(3) . . ? N2 C16 C9 117.1(3) . . ? N2 C17 C18 111.0(3) . . ? N2 C17 C25 113.1(3) . . ? C18 C17 C25 106.8(3) . . ? N2 C17 H17A 108.6 . . ? C18 C17 H17A 108.6 . . ? C25 C17 H17A 108.6 . . ? C19 C18 C17 116.6(3) . . ? C19 C18 H18A 108.1 . . ? C17 C18 H18A 108.1 . . ? C19 C18 H18B 108.1 . . ? C17 C18 H18B 108.1 . . ? H18A C18 H18B 107.3 . . ? C20 C19 C24 117.8(3) . . ? C20 C19 C18 122.4(3) . . ? C24 C19 C18 119.7(3) . . ? C19 C20 C21 121.3(3) . . ? C19 C20 H20A 119.3 . . ? C21 C20 H20A 119.3 . . ? C22 C21 C20 120.5(3) . . ? C22 C21 H21A 119.8 . . ? C20 C21 H21A 119.8 . . ? C21 C22 C23 118.1(3) . . ? C21 C22 H22A 120.9 . . ? C23 C22 H22A 120.9 . . ? C24 C23 C22 121.5(3) . . ? C24 C23 H23A 119.2 . . ? C22 C23 H23A 119.2 . . ? C23 C24 C19 120.7(3) . . ? C23 C24 H24A 119.7 . . ? C19 C24 H24A 119.7 . . ? O3 C25 N3 122.5(3) . . ? O3 C25 C17 120.5(3) . . ? N3 C25 C17 116.9(3) . . ? N3 C26 H26A 109.5 . . ? N3 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N3 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 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 C6 N1 C5 O1 -171.4(3) . . . . ? C9 N1 C5 O1 -5.0(4) . . . . ? C6 N1 C5 C4 4.6(5) . . . . ? C9 N1 C5 C4 170.9(3) . . . . ? C3 C4 C5 O1 -141.6(3) . . . . ? C2 C4 C5 O1 -20.9(4) . . . . ? C1 C4 C5 O1 96.2(3) . . . . ? C3 C4 C5 N1 42.4(4) . . . . ? C2 C4 C5 N1 163.1(3) . . . . ? C1 C4 C5 N1 -79.8(4) . . . . ? C5 N1 C6 C7 155.2(3) . . . . ? C9 N1 C6 C7 -11.8(3) . . . . ? N1 C6 C7 C8 31.2(3) . . . . ? C6 C7 C8 C10 -165.3(3) . . . . ? C6 C7 C8 C9 -38.6(3) . . . . ? C5 N1 C9 C16 -61.8(4) . . . . ? C6 N1 C9 C16 106.9(3) . . . . ? C5 N1 C9 C8 179.1(3) . . . . ? C6 N1 C9 C8 -12.1(3) . . . . ? C10 C8 C9 N1 160.1(3) . . . . ? C7 C8 C9 N1 30.7(3) . . . . ? C10 C8 C9 C16 42.7(4) . . . . ? C7 C8 C9 C16 -86.7(3) . . . . ? C7 C8 C10 C11 -160.8(3) . . . . ? C9 C8 C10 C11 78.4(4) . . . . ? C7 C8 C10 C15 20.2(5) . . . . ? C9 C8 C10 C15 -100.6(4) . . . . ? C15 C10 C11 C12 1.9(5) . . . . ? C8 C10 C11 C12 -177.2(3) . . . . ? C10 C11 C12 C13 -1.5(6) . . . . ? C11 C12 C13 C14 0.0(6) . . . . ? C12 C13 C14 C15 1.0(6) . . . . ? C13 C14 C15 C10 -0.6(6) . . . . ? C11 C10 C15 C14 -0.9(5) . . . . ? C8 C10 C15 C14 178.2(4) . . . . ? C17 N2 C16 O2 3.5(5) . . . . ? C17 N2 C16 C9 -176.8(3) . . . . ? N1 C9 C16 O2 -46.5(4) . . . . ? C8 C9 C16 O2 67.2(4) . . . . ? N1 C9 C16 N2 133.8(3) . . . . ? C8 C9 C16 N2 -112.4(3) . . . . ? C16 N2 C17 C18 -178.1(3) . . . . ? C16 N2 C17 C25 61.9(4) . . . . ? N2 C17 C18 C19 60.5(4) . . . . ? C25 C17 C18 C19 -175.8(3) . . . . ? C17 C18 C19 C20 55.7(4) . . . . ? C17 C18 C19 C24 -126.2(3) . . . . ? C24 C19 C20 C21 -1.4(5) . . . . ? C18 C19 C20 C21 176.7(3) . . . . ? C19 C20 C21 C22 1.4(5) . . . . ? C20 C21 C22 C23 -0.7(5) . . . . ? C21 C22 C23 C24 0.2(5) . . . . ? C22 C23 C24 C19 -0.2(5) . . . . ? C20 C19 C24 C23 0.8(5) . . . . ? C18 C19 C24 C23 -177.3(3) . . . . ? C26 N3 C25 O3 3.4(5) . . . . ? C26 N3 C25 C17 179.2(3) . . . . ? N2 C17 C25 O3 -158.3(3) . . . . ? C18 C17 C25 O3 79.3(4) . . . . ? N2 C17 C25 N3 25.8(4) . . . . ? C18 C17 C25 N3 -96.6(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3 O1 1.05 1.94 2.904(3) 150.6 . N2 H2 O3 1.03 1.92 2.915(3) 162.0 1_455 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.210 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.046 # Attachment '3.cif' data_Piv-(S,R)-(betaPh)Pro-L-Phe-NHMe_compound_3 _database_code_depnum_ccdc_archive 'CCDC 842883' #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '(2S,3R)-N-(tert-butylcarbonyl)-3-phenylprolyl-(S)-N'-methylphenylalaninamide' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H33 N3 O3' _chemical_formula_sum 'C26 H33 N3 O3' _chemical_formula_weight 435.55 _chemical_absolute_configuration syn 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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.5504(3) _cell_length_b 25.2883(7) _cell_length_c 10.0653(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.733(3) _cell_angle_gamma 90.00 _cell_volume 2361.41(12) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.225 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Xcalibur, Sapphire3' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 57501 _diffrn_reflns_av_R_equivalents 0.0442 _diffrn_reflns_av_sigmaI/netI 0.0647 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 27.50 _reflns_number_total 10806 _reflns_number_gt 7431 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0310P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10806 _refine_ls_number_parameters 579 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0490 _refine_ls_R_factor_gt 0.0313 _refine_ls_wR_factor_ref 0.0584 _refine_ls_wR_factor_gt 0.0567 _refine_ls_goodness_of_fit_ref 0.851 _refine_ls_restrained_S_all 0.851 _refine_ls_shift/su_max 0.001 _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 O1 O 0.29190(10) 0.31439(3) 0.11519(9) 0.0284(2) Uani 1 1 d . . . O2 O 0.57226(9) 0.24116(3) 0.18425(9) 0.0236(2) Uani 1 1 d . . . O3 O 0.57924(12) 0.25955(4) 0.57630(10) 0.0414(3) Uani 1 1 d . . . N1 N 0.36503(12) 0.27632(4) -0.05572(11) 0.0232(3) Uani 1 1 d . . . N2 N 0.38250(11) 0.20588(4) 0.25143(10) 0.0213(3) Uani 1 1 d . . . H2 H 0.2899 0.2003 0.2251 0.026 Uiso 1 1 d R . . N3 N 0.42658(13) 0.29951(4) 0.40114(12) 0.0310(3) Uani 1 1 d . . . H3 H 0.3819 0.2962 0.3139 0.037 Uiso 1 1 d R . . C1 C 0.3247(2) 0.41553(6) 0.05856(18) 0.0466(5) Uani 1 1 d . . . H1A H 0.3357 0.4515 0.0265 0.070 Uiso 1 1 calc R . . H1B H 0.3948 0.4096 0.1456 0.070 Uiso 1 1 calc R . . H1C H 0.2269 0.4110 0.0715 0.070 Uiso 1 1 calc R . . C2 C 0.23829(19) 0.38629(6) -0.18178(17) 0.0447(4) Uani 1 1 d . . . H2A H 0.2521 0.4219 -0.2147 0.067 Uiso 1 1 calc R . . H2B H 0.1412 0.3833 -0.1660 0.067 Uiso 1 1 calc R . . H2C H 0.2500 0.3602 -0.2504 0.067 Uiso 1 1 calc R . . C3 C 0.50319(17) 0.38381(6) -0.06740(19) 0.0449(4) Uani 1 1 d . . . H3A H 0.5120 0.4195 -0.1023 0.067 Uiso 1 1 calc R . . H3B H 0.5219 0.3577 -0.1331 0.067 Uiso 1 1 calc R . . H3C H 0.5733 0.3792 0.0203 0.067 Uiso 1 1 calc R . . C4 C 0.35058(16) 0.37590(5) -0.04722(16) 0.0319(4) Uani 1 1 d . . . C5 C 0.33296(14) 0.32008(5) 0.00890(14) 0.0242(3) Uani 1 1 d . . . C6 C 0.41188(18) 0.27080(5) -0.18398(14) 0.0316(4) Uani 1 1 d . . . H6A H 0.5151 0.2799 -0.1708 0.038 Uiso 1 1 calc R . . H6B H 0.3540 0.2935 -0.2567 0.038 Uiso 1 1 calc R . . C7 C 0.38560(18) 0.21295(5) -0.21794(14) 0.0339(4) Uani 1 1 d . . . H7A H 0.4470 0.2002 -0.2779 0.041 Uiso 1 1 calc R . . H7B H 0.2832 0.2063 -0.2631 0.041 Uiso 1 1 calc R . . C8 C 0.42709(15) 0.18675(5) -0.07748(13) 0.0226(3) Uani 1 1 d . . . H8A H 0.5341 0.1896 -0.0439 0.027 Uiso 1 1 calc R . . C9 C 0.35796(14) 0.22462(5) 0.00990(13) 0.0209(3) Uani 1 1 d . . . H9A H 0.2559 0.2144 0.0057 0.025 Uiso 1 1 calc R . . C10 C 0.38803(14) 0.12940(5) -0.07248(12) 0.0213(3) Uani 1 1 d . . . C11 C 0.25262(16) 0.10981(5) -0.13648(14) 0.0296(4) Uani 1 1 d . . . H11A H 0.1791 0.1336 -0.1806 0.036 Uiso 1 1 calc R . . C12 C 0.22384(17) 0.05657(6) -0.13675(15) 0.0347(4) Uani 1 1 d . . . H12A H 0.1314 0.0438 -0.1826 0.042 Uiso 1 1 calc R . . C13 C 0.32816(17) 0.02148(6) -0.07100(15) 0.0317(4) Uani 1 1 d . . . H13A H 0.3084 -0.0154 -0.0722 0.038 Uiso 1 1 calc R . . C14 C 0.46063(17) 0.04041(5) -0.00402(14) 0.0305(4) Uani 1 1 d . . . H14A H 0.5321 0.0166 0.0438 0.037 Uiso 1 1 calc R . . C15 C 0.49111(15) 0.09379(5) -0.00541(13) 0.0243(3) Uani 1 1 d . . . H15A H 0.5839 0.1062 0.0402 0.029 Uiso 1 1 calc R . . C16 C 0.44722(15) 0.22531(5) 0.15709(13) 0.0192(3) Uani 1 1 d . . . C17 C 0.45462(14) 0.20315(5) 0.39600(13) 0.0237(3) Uani 1 1 d . . . H17A H 0.3817 0.1880 0.4421 0.028 Uiso 1 1 calc R . . C18 C 0.58259(15) 0.16414(5) 0.42733(14) 0.0287(3) Uani 1 1 d . . . H18A H 0.6270 0.1631 0.3479 0.034 Uiso 1 1 calc R . . H18B H 0.6561 0.1775 0.5068 0.034 Uiso 1 1 calc R . . C19 C 0.54101(14) 0.10908(5) 0.45760(14) 0.0255(3) Uani 1 1 d . . . C20 C 0.53780(17) 0.09416(6) 0.58920(15) 0.0331(4) Uani 1 1 d . . . H20A H 0.5594 0.1196 0.6605 0.040 Uiso 1 1 calc R . . C21 C 0.50408(18) 0.04332(6) 0.61929(17) 0.0433(4) Uani 1 1 d . . . H21A H 0.5017 0.0341 0.7102 0.052 Uiso 1 1 calc R . . C22 C 0.47386(18) 0.00598(6) 0.5170(2) 0.0472(5) Uani 1 1 d . . . H22A H 0.4521 -0.0293 0.5373 0.057 Uiso 1 1 calc R . . C23 C 0.47525(18) 0.01995(7) 0.38603(19) 0.0480(5) Uani 1 1 d . . . H23A H 0.4534 -0.0057 0.3151 0.058 Uiso 1 1 calc R . . C24 C 0.50815(17) 0.07096(6) 0.35653(15) 0.0368(4) Uani 1 1 d . . . H24A H 0.5083 0.0801 0.2650 0.044 Uiso 1 1 calc R . . C25 C 0.49535(16) 0.25711(6) 0.46387(14) 0.0279(3) Uani 1 1 d . . . C26 C 0.45651(18) 0.35154(6) 0.46196(17) 0.0400(4) Uani 1 1 d . . . H26A H 0.4188 0.3538 0.5442 0.060 Uiso 1 1 calc R . . H26B H 0.4101 0.3785 0.3962 0.060 Uiso 1 1 calc R . . H26C H 0.5609 0.3575 0.4866 0.060 Uiso 1 1 calc R . . O1' O 0.81631(9) 0.12672(3) 0.20692(9) 0.0249(2) Uani 1 1 d . . . O2' O 1.05990(9) 0.20160(3) 0.13181(9) 0.0229(2) Uani 1 1 d . . . O3' O 0.91481(12) 0.16939(4) -0.24557(10) 0.0384(3) Uani 1 1 d . . . N1' N 0.96480(12) 0.17245(4) 0.37005(10) 0.0208(3) Uani 1 1 d . . . N2' N 0.83434(11) 0.23305(4) 0.04769(10) 0.0204(3) Uani 1 1 d . . . H2' H 0.7599 0.2384 0.0762 0.025 Uiso 1 1 d R . . N3' N 0.82500(13) 0.13554(4) -0.07602(12) 0.0271(3) Uani 1 1 d . . . H3' H 0.8073 0.1411 0.0050 0.032 Uiso 1 1 d R . . C1' C 0.8997(2) 0.02870(6) 0.28484(16) 0.0427(4) Uani 1 1 d . . . H1D H 0.9319 0.0328 0.1999 0.064 Uiso 1 1 calc R . . H1E H 0.7943 0.0304 0.2646 0.064 Uiso 1 1 calc R . . H1F H 0.9322 -0.0056 0.3265 0.064 Uiso 1 1 calc R . . C2' C 0.91186(18) 0.06487(6) 0.51563(15) 0.0372(4) Uani 1 1 d . . . H2D H 0.9507 0.0930 0.5810 0.056 Uiso 1 1 calc R . . H2E H 0.9456 0.0305 0.5556 0.056 Uiso 1 1 calc R . . H2F H 0.8063 0.0659 0.4944 0.056 Uiso 1 1 calc R . . C3' C 1.12796(18) 0.06988(7) 0.41445(19) 0.0518(5) Uani 1 1 d . . . H3D H 1.1700 0.0984 0.4771 0.078 Uiso 1 1 calc R . . H3E H 1.1594 0.0734 0.3290 0.078 Uiso 1 1 calc R . . H3F H 1.1599 0.0357 0.4567 0.078 Uiso 1 1 calc R . . C4' C 0.96360(16) 0.07312(5) 0.38401(14) 0.0272(3) Uani 1 1 d . . . C5' C 0.90931(14) 0.12592(5) 0.31526(13) 0.0204(3) Uani 1 1 d . . . C6' C 1.06171(15) 0.18444(5) 0.50356(13) 0.0254(3) Uani 1 1 d . . . H6D H 1.1638 0.1787 0.5019 0.030 Uiso 1 1 calc R . . H6E H 1.0383 0.1626 0.5770 0.030 Uiso 1 1 calc R . . C7' C 1.03177(16) 0.24197(6) 0.52240(13) 0.0278(3) Uani 1 1 d . . . H7D H 1.1142 0.2592 0.5860 0.033 Uiso 1 1 calc R . . H7E H 0.9441 0.2466 0.5575 0.033 Uiso 1 1 calc R . . C8' C 1.01001(15) 0.26431(5) 0.37729(13) 0.0221(3) Uani 1 1 d . . . H8D H 1.1058 0.2639 0.3533 0.026 Uiso 1 1 calc R . . C9' C 0.91661(14) 0.22101(5) 0.29257(12) 0.0193(3) Uani 1 1 d . . . H9D H 0.8122 0.2276 0.2872 0.023 Uiso 1 1 calc R . . C10' C 0.95541(15) 0.32025(5) 0.36203(13) 0.0243(3) Uani 1 1 d . . . C11' C 0.81196(17) 0.33402(6) 0.33160(15) 0.0336(4) Uani 1 1 d . . . H11D H 0.7403 0.3072 0.3148 0.040 Uiso 1 1 calc R . . C12' C 0.77090(18) 0.38691(6) 0.32517(16) 0.0374(4) Uani 1 1 d . . . H12D H 0.6714 0.3957 0.3023 0.045 Uiso 1 1 calc R . . C13' C 0.87118(19) 0.42622(6) 0.35116(16) 0.0414(4) Uani 1 1 d . . . H13D H 0.8425 0.4623 0.3481 0.050 Uiso 1 1 calc R . . C14' C 1.0134(2) 0.41289(7) 0.3816(2) 0.0616(6) Uani 1 1 d . . . H14D H 1.0846 0.4399 0.4003 0.074 Uiso 1 1 calc R . . C15' C 1.05496(19) 0.36049(6) 0.3856(2) 0.0510(5) Uani 1 1 d . . . H15D H 1.1547 0.3521 0.4052 0.061 Uiso 1 1 calc R . . C16' C 0.94379(15) 0.21706(5) 0.15018(13) 0.0190(3) Uani 1 1 d . . . C17' C 0.84259(15) 0.23158(5) -0.09483(13) 0.0225(3) Uani 1 1 d . . . H17D H 0.7462 0.2431 -0.1502 0.027 Uiso 1 1 calc R . . C18' C 0.95270(16) 0.27093(5) -0.12549(14) 0.0268(3) Uani 1 1 d . . . H18D H 1.0437 0.2672 -0.0545 0.032 Uiso 1 1 calc R . . H18E H 0.9732 0.2616 -0.2145 0.032 Uiso 1 1 calc R . . C19' C 0.90544(15) 0.32789(5) -0.13053(14) 0.0254(3) Uani 1 1 d . . . C20' C 0.83799(16) 0.35082(6) -0.25413(15) 0.0326(4) Uani 1 1 d . . . H20D H 0.8153 0.3297 -0.3345 0.039 Uiso 1 1 calc R . . C21' C 0.80320(18) 0.40394(6) -0.26225(16) 0.0394(4) Uani 1 1 d . . . H21D H 0.7581 0.4192 -0.3479 0.047 Uiso 1 1 calc R . . C22' C 0.83396(17) 0.43472(6) -0.14594(17) 0.0380(4) Uani 1 1 d . . . H22D H 0.8104 0.4713 -0.1512 0.046 Uiso 1 1 calc R . . C23' C 0.89880(17) 0.41237(6) -0.02252(16) 0.0368(4) Uani 1 1 d . . . H23D H 0.9192 0.4334 0.0579 0.044 Uiso 1 1 calc R . . C24' C 0.93466(16) 0.35909(6) -0.01474(15) 0.0311(4) Uani 1 1 d . . . H24D H 0.9798 0.3439 0.0711 0.037 Uiso 1 1 calc R . . C25' C 0.86760(15) 0.17542(6) -0.14362(14) 0.0260(3) Uani 1 1 d . . . C26' C 0.84568(18) 0.08098(6) -0.11016(15) 0.0367(4) Uani 1 1 d . . . H26D H 0.8377 0.0779 -0.2087 0.055 Uiso 1 1 calc R . . H26E H 0.7719 0.0589 -0.0846 0.055 Uiso 1 1 calc R . . H26F H 0.9414 0.0691 -0.0603 0.055 Uiso 1 1 calc 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 O1 0.0279(6) 0.0232(5) 0.0352(6) -0.0002(4) 0.0097(5) 0.0044(4) O2 0.0192(5) 0.0233(5) 0.0278(5) 0.0010(4) 0.0047(4) -0.0022(4) O3 0.0474(7) 0.0466(7) 0.0259(6) -0.0047(5) 0.0001(5) -0.0053(5) N1 0.0245(7) 0.0181(7) 0.0266(6) 0.0026(5) 0.0054(5) 0.0017(5) N2 0.0159(6) 0.0227(7) 0.0250(6) -0.0004(5) 0.0046(5) -0.0026(5) N3 0.0351(8) 0.0282(8) 0.0293(7) -0.0085(6) 0.0070(6) 0.0003(6) C1 0.0520(11) 0.0188(9) 0.0748(13) -0.0011(8) 0.0268(10) -0.0015(8) C2 0.0459(11) 0.0297(9) 0.0616(11) 0.0223(8) 0.0189(9) 0.0095(8) C3 0.0369(10) 0.0253(9) 0.0769(13) -0.0030(8) 0.0223(9) -0.0074(8) C4 0.0274(9) 0.0182(8) 0.0523(10) 0.0062(7) 0.0140(7) -0.0005(7) C5 0.0161(8) 0.0206(8) 0.0331(9) 0.0006(6) 0.0007(6) 0.0009(6) C6 0.0424(10) 0.0256(9) 0.0277(8) 0.0045(6) 0.0100(7) 0.0000(7) C7 0.0521(11) 0.0241(9) 0.0258(8) 0.0016(6) 0.0100(7) 0.0010(7) C8 0.0234(8) 0.0213(8) 0.0224(7) -0.0011(6) 0.0039(6) 0.0000(6) C9 0.0195(7) 0.0160(7) 0.0269(7) 0.0034(6) 0.0050(6) 0.0011(6) C10 0.0255(8) 0.0193(8) 0.0201(7) -0.0013(6) 0.0073(6) 0.0015(6) C11 0.0254(9) 0.0263(9) 0.0339(8) -0.0006(6) 0.0007(7) 0.0030(6) C12 0.0297(9) 0.0304(10) 0.0424(9) -0.0065(7) 0.0056(7) -0.0081(7) C13 0.0403(10) 0.0179(8) 0.0386(9) -0.0016(7) 0.0129(7) -0.0024(7) C14 0.0348(10) 0.0255(9) 0.0311(8) 0.0053(6) 0.0078(7) 0.0074(7) C15 0.0238(8) 0.0234(9) 0.0250(8) -0.0018(6) 0.0041(6) -0.0005(6) C16 0.0184(8) 0.0110(7) 0.0280(7) -0.0007(6) 0.0052(6) 0.0034(6) C17 0.0207(8) 0.0286(8) 0.0230(7) 0.0036(6) 0.0076(6) -0.0034(6) C18 0.0239(8) 0.0325(9) 0.0296(8) 0.0038(7) 0.0059(6) -0.0007(7) C19 0.0195(8) 0.0293(9) 0.0270(8) 0.0019(6) 0.0042(6) 0.0024(6) C20 0.0408(10) 0.0317(10) 0.0260(8) 0.0014(7) 0.0061(7) 0.0045(7) C21 0.0457(11) 0.0431(11) 0.0437(10) 0.0160(8) 0.0156(8) 0.0046(8) C22 0.0392(11) 0.0283(10) 0.0738(14) 0.0074(9) 0.0128(9) 0.0008(8) C23 0.0433(11) 0.0418(12) 0.0587(12) -0.0182(9) 0.0117(9) -0.0067(8) C24 0.0365(10) 0.0447(11) 0.0285(8) -0.0045(7) 0.0064(7) -0.0038(8) C25 0.0259(8) 0.0349(10) 0.0250(8) -0.0014(7) 0.0102(7) -0.0048(7) C26 0.0403(10) 0.0337(10) 0.0476(10) -0.0143(7) 0.0133(8) -0.0066(8) O1' 0.0264(5) 0.0239(5) 0.0228(5) -0.0008(4) 0.0024(4) -0.0032(4) O2' 0.0184(5) 0.0269(5) 0.0240(5) 0.0010(4) 0.0065(4) 0.0028(4) O3' 0.0573(8) 0.0342(6) 0.0307(6) -0.0026(5) 0.0245(5) 0.0042(5) N1' 0.0203(6) 0.0242(7) 0.0169(5) 0.0001(5) 0.0027(5) -0.0008(5) N2' 0.0183(6) 0.0252(7) 0.0190(6) 0.0000(5) 0.0066(5) 0.0023(5) N3' 0.0333(7) 0.0263(7) 0.0246(6) -0.0068(5) 0.0125(5) -0.0038(6) C1' 0.0682(13) 0.0186(8) 0.0408(9) -0.0040(7) 0.0118(8) 0.0022(8) C2' 0.0499(11) 0.0258(9) 0.0351(9) 0.0043(7) 0.0087(8) 0.0006(7) C3' 0.0352(11) 0.0385(11) 0.0840(13) 0.0062(9) 0.0185(10) 0.0112(8) C4' 0.0289(9) 0.0185(8) 0.0342(8) 0.0013(6) 0.0076(7) 0.0033(6) C5' 0.0210(8) 0.0208(8) 0.0221(7) -0.0021(6) 0.0106(6) -0.0007(6) C6' 0.0265(8) 0.0264(9) 0.0213(7) 0.0006(6) 0.0019(6) -0.0019(6) C7' 0.0300(8) 0.0302(9) 0.0215(7) -0.0030(6) 0.0025(6) -0.0020(7) C8' 0.0216(8) 0.0235(8) 0.0212(7) -0.0023(6) 0.0052(6) -0.0014(6) C9' 0.0180(7) 0.0178(7) 0.0222(7) 0.0003(5) 0.0052(6) 0.0012(6) C10' 0.0302(9) 0.0236(9) 0.0191(7) -0.0050(6) 0.0060(6) -0.0028(7) C11' 0.0304(9) 0.0253(9) 0.0458(10) -0.0055(7) 0.0106(7) -0.0043(7) C12' 0.0349(10) 0.0306(10) 0.0453(10) -0.0017(7) 0.0065(7) 0.0074(8) C13' 0.0536(12) 0.0259(10) 0.0443(10) -0.0023(7) 0.0108(9) 0.0035(8) C14' 0.0497(13) 0.0246(11) 0.1072(17) -0.0147(10) 0.0121(11) -0.0112(9) C15' 0.0299(10) 0.0270(10) 0.0904(15) -0.0096(9) 0.0031(9) -0.0036(8) C16' 0.0192(8) 0.0142(7) 0.0237(7) -0.0039(6) 0.0053(6) -0.0048(6) C17' 0.0200(7) 0.0272(8) 0.0200(7) -0.0009(6) 0.0043(6) 0.0027(6) C18' 0.0275(8) 0.0293(9) 0.0249(7) 0.0014(6) 0.0090(6) 0.0022(7) C19' 0.0220(8) 0.0275(9) 0.0283(8) 0.0032(6) 0.0089(6) 0.0006(6) C20' 0.0364(10) 0.0272(10) 0.0321(9) -0.0009(7) 0.0041(7) 0.0003(7) C21' 0.0388(10) 0.0406(11) 0.0364(9) 0.0094(8) 0.0041(7) 0.0033(8) C22' 0.0371(10) 0.0261(9) 0.0529(11) 0.0038(8) 0.0153(8) 0.0041(7) C23' 0.0354(10) 0.0374(10) 0.0407(10) -0.0093(8) 0.0150(8) -0.0020(8) C24' 0.0290(9) 0.0371(10) 0.0286(8) 0.0006(7) 0.0092(7) 0.0014(7) C25' 0.0237(8) 0.0300(9) 0.0229(7) -0.0021(6) 0.0028(6) 0.0027(7) C26' 0.0443(11) 0.0293(10) 0.0382(9) -0.0056(7) 0.0135(8) -0.0020(7) _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 O1 C5 1.2321(16) . ? O2 C16 1.2273(15) . ? O3 C25 1.2230(16) . ? N1 C5 1.3548(17) . ? N1 C6 1.4699(17) . ? N1 C9 1.4736(16) . ? N2 C16 1.3431(16) . ? N2 C17 1.4563(16) . ? N2 H2 0.8719 . ? N3 C25 1.3353(18) . ? N3 C26 1.4508(18) . ? N3 H3 0.8841 . ? C1 C4 1.525(2) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C4 1.538(2) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.532(2) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C5 1.544(2) . ? C6 C7 1.5098(19) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.5261(18) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C10 1.5012(19) . ? C8 C9 1.5499(18) . ? C8 H8A 1.0000 . ? C9 C16 1.5239(18) . ? C9 H9A 1.0000 . ? C10 C15 1.3857(18) . ? C10 C11 1.3919(19) . ? C11 C12 1.374(2) . ? C11 H11A 0.9500 . ? C12 C13 1.380(2) . ? C12 H12A 0.9500 . ? C13 C14 1.371(2) . ? C13 H13A 0.9500 . ? C14 C15 1.3819(19) . ? C14 H14A 0.9500 . ? C15 H15A 0.9500 . ? C17 C25 1.5340(19) . ? C17 C18 1.5438(19) . ? C17 H17A 1.0000 . ? C18 C19 1.4989(19) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C24 1.383(2) . ? C19 C20 1.3846(19) . ? C20 C21 1.377(2) . ? C20 H20A 0.9500 . ? C21 C22 1.376(2) . ? C21 H21A 0.9500 . ? C22 C23 1.368(2) . ? C22 H22A 0.9500 . ? C23 C24 1.377(2) . ? C23 H23A 0.9500 . ? C24 H24A 0.9500 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? O1' C5' 1.2323(15) . ? O2' C16' 1.2305(15) . ? O3' C25' 1.2244(16) . ? N1' C5' 1.3532(17) . ? N1' C9' 1.4687(16) . ? N1' C6' 1.4711(16) . ? N2' C16' 1.3448(16) . ? N2' C17' 1.4557(15) . ? N2' H2' 0.8387 . ? N3' C25' 1.3331(17) . ? N3' C26' 1.4467(18) . ? N3' H3' 0.8830 . ? C1' C4' 1.530(2) . ? C1' H1D 0.9800 . ? C1' H1E 0.9800 . ? C1' H1F 0.9800 . ? C2' C4' 1.534(2) . ? C2' H2D 0.9800 . ? C2' H2E 0.9800 . ? C2' H2F 0.9800 . ? C3' C4' 1.528(2) . ? C3' H3D 0.9800 . ? C3' H3E 0.9800 . ? C3' H3F 0.9800 . ? C4' C5' 1.5362(19) . ? C6' C7' 1.503(2) . ? C6' H6D 0.9900 . ? C6' H6E 0.9900 . ? C7' C8' 1.5335(18) . ? C7' H7D 0.9900 . ? C7' H7E 0.9900 . ? C8' C10' 1.5030(19) . ? C8' C9' 1.5365(18) . ? C8' H8D 1.0000 . ? C9' C16' 1.5192(17) . ? C9' H9D 1.0000 . ? C10' C15' 1.374(2) . ? C10' C11' 1.376(2) . ? C11' C12' 1.391(2) . ? C11' H11D 0.9500 . ? C12' C13' 1.362(2) . ? C12' H12D 0.9500 . ? C13' C14' 1.362(2) . ? C13' H13D 0.9500 . ? C14' C15' 1.381(2) . ? C14' H14D 0.9500 . ? C15' H15D 0.9500 . ? C17' C18' 1.5316(19) . ? C17' C25' 1.540(2) . ? C17' H17D 1.0000 . ? C18' C19' 1.507(2) . ? C18' H18D 0.9900 . ? C18' H18E 0.9900 . ? C19' C24' 1.3799(19) . ? C19' C20' 1.3850(19) . ? C20' C21' 1.382(2) . ? C20' H20D 0.9500 . ? C21' C22' 1.378(2) . ? C21' H21D 0.9500 . ? C22' C23' 1.371(2) . ? C22' H22D 0.9500 . ? C23' C24' 1.388(2) . ? C23' H23D 0.9500 . ? C24' H24D 0.9500 . ? C26' H26D 0.9800 . ? C26' H26E 0.9800 . ? C26' H26F 0.9800 . ? 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 C5 N1 C6 130.53(11) . . ? C5 N1 C9 118.02(11) . . ? C6 N1 C9 111.42(10) . . ? C16 N2 C17 122.40(11) . . ? C16 N2 H2 116.6 . . ? C17 N2 H2 120.0 . . ? C25 N3 C26 120.22(12) . . ? C25 N3 H3 117.5 . . ? C26 N3 H3 120.3 . . ? C4 C1 H1A 109.5 . . ? C4 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C4 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C4 C2 H2A 109.5 . . ? C4 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C4 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C4 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C1 C4 C3 108.91(13) . . ? C1 C4 C2 107.93(13) . . ? C3 C4 C2 110.34(13) . . ? C1 C4 C5 107.19(13) . . ? C3 C4 C5 110.95(12) . . ? C2 C4 C5 111.39(12) . . ? O1 C5 N1 118.45(12) . . ? O1 C5 C4 120.59(12) . . ? N1 C5 C4 120.94(13) . . ? N1 C6 C7 102.83(11) . . ? N1 C6 H6A 111.2 . . ? C7 C6 H6A 111.2 . . ? N1 C6 H6B 111.2 . . ? C7 C6 H6B 111.2 . . ? H6A C6 H6B 109.1 . . ? C6 C7 C8 102.61(11) . . ? C6 C7 H7A 111.2 . . ? C8 C7 H7A 111.2 . . ? C6 C7 H7B 111.2 . . ? C8 C7 H7B 111.2 . . ? H7A C7 H7B 109.2 . . ? C10 C8 C7 116.01(11) . . ? C10 C8 C9 115.80(11) . . ? C7 C8 C9 101.86(10) . . ? C10 C8 H8A 107.5 . . ? C7 C8 H8A 107.5 . . ? C9 C8 H8A 107.5 . . ? N1 C9 C16 110.54(10) . . ? N1 C9 C8 102.88(10) . . ? C16 C9 C8 110.08(10) . . ? N1 C9 H9A 111.0 . . ? C16 C9 H9A 111.0 . . ? C8 C9 H9A 111.0 . . ? C15 C10 C11 117.95(13) . . ? C15 C10 C8 119.38(12) . . ? C11 C10 C8 122.64(12) . . ? C12 C11 C10 120.88(13) . . ? C12 C11 H11A 119.6 . . ? C10 C11 H11A 119.6 . . ? C11 C12 C13 120.51(14) . . ? C11 C12 H12A 119.7 . . ? C13 C12 H12A 119.7 . . ? C14 C13 C12 119.23(14) . . ? C14 C13 H13A 120.4 . . ? C12 C13 H13A 120.4 . . ? C13 C14 C15 120.54(13) . . ? C13 C14 H14A 119.7 . . ? C15 C14 H14A 119.7 . . ? C14 C15 C10 120.85(13) . . ? C14 C15 H15A 119.6 . . ? C10 C15 H15A 119.6 . . ? O2 C16 N2 123.28(12) . . ? O2 C16 C9 120.70(12) . . ? N2 C16 C9 115.97(12) . . ? N2 C17 C25 114.38(11) . . ? N2 C17 C18 113.45(11) . . ? C25 C17 C18 111.88(11) . . ? N2 C17 H17A 105.4 . . ? C25 C17 H17A 105.4 . . ? C18 C17 H17A 105.4 . . ? C19 C18 C17 113.58(11) . . ? C19 C18 H18A 108.8 . . ? C17 C18 H18A 108.8 . . ? C19 C18 H18B 108.8 . . ? C17 C18 H18B 108.8 . . ? H18A C18 H18B 107.7 . . ? C24 C19 C20 117.46(13) . . ? C24 C19 C18 121.54(13) . . ? C20 C19 C18 120.98(13) . . ? C21 C20 C19 121.64(14) . . ? C21 C20 H20A 119.2 . . ? C19 C20 H20A 119.2 . . ? C22 C21 C20 119.66(15) . . ? C22 C21 H21A 120.2 . . ? C20 C21 H21A 120.2 . . ? C23 C22 C21 119.70(16) . . ? C23 C22 H22A 120.1 . . ? C21 C22 H22A 120.1 . . ? C22 C23 C24 120.31(15) . . ? C22 C23 H23A 119.8 . . ? C24 C23 H23A 119.8 . . ? C23 C24 C19 121.22(14) . . ? C23 C24 H24A 119.4 . . ? C19 C24 H24A 119.4 . . ? O3 C25 N3 122.52(13) . . ? O3 C25 C17 119.88(13) . . ? N3 C25 C17 117.35(12) . . ? N3 C26 H26A 109.5 . . ? N3 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N3 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C5' N1' C9' 117.88(10) . . ? C5' N1' C6' 130.70(11) . . ? C9' N1' C6' 111.26(10) . . ? C16' N2' C17' 122.29(11) . . ? C16' N2' H2' 110.7 . . ? C17' N2' H2' 126.2 . . ? C25' N3' C26' 121.65(12) . . ? C25' N3' H3' 120.0 . . ? C26' N3' H3' 116.0 . . ? C4' C1' H1D 109.5 . . ? C4' C1' H1E 109.5 . . ? H1D C1' H1E 109.5 . . ? C4' C1' H1F 109.5 . . ? H1D C1' H1F 109.5 . . ? H1E C1' H1F 109.5 . . ? C4' C2' H2D 109.5 . . ? C4' C2' H2E 109.5 . . ? H2D C2' H2E 109.5 . . ? C4' C2' H2F 109.5 . . ? H2D C2' H2F 109.5 . . ? H2E C2' H2F 109.5 . . ? C4' C3' H3D 109.5 . . ? C4' C3' H3E 109.5 . . ? H3D C3' H3E 109.5 . . ? C4' C3' H3F 109.5 . . ? H3D C3' H3F 109.5 . . ? H3E C3' H3F 109.5 . . ? C3' C4' C1' 108.83(13) . . ? C3' C4' C2' 110.22(13) . . ? C1' C4' C2' 107.66(13) . . ? C3' C4' C5' 110.96(12) . . ? C1' C4' C5' 107.73(12) . . ? C2' C4' C5' 111.33(11) . . ? O1' C5' N1' 118.46(12) . . ? O1' C5' C4' 120.55(12) . . ? N1' C5' C4' 120.97(11) . . ? N1' C6' C7' 102.55(10) . . ? N1' C6' H6D 111.3 . . ? C7' C6' H6D 111.3 . . ? N1' C6' H6E 111.3 . . ? C7' C6' H6E 111.3 . . ? H6D C6' H6E 109.2 . . ? C6' C7' C8' 102.90(10) . . ? C6' C7' H7D 111.2 . . ? C8' C7' H7D 111.2 . . ? C6' C7' H7E 111.2 . . ? C8' C7' H7E 111.2 . . ? H7D C7' H7E 109.1 . . ? C10' C8' C7' 114.17(10) . . ? C10' C8' C9' 118.20(11) . . ? C7' C8' C9' 101.28(10) . . ? C10' C8' H8D 107.5 . . ? C7' C8' H8D 107.5 . . ? C9' C8' H8D 107.5 . . ? N1' C9' C16' 110.11(10) . . ? N1' C9' C8' 103.51(10) . . ? C16' C9' C8' 111.33(11) . . ? N1' C9' H9D 110.6 . . ? C16' C9' H9D 110.6 . . ? C8' C9' H9D 110.6 . . ? C15' C10' C11' 117.55(14) . . ? C15' C10' C8' 118.05(13) . . ? C11' C10' C8' 124.33(13) . . ? C10' C11' C12' 120.57(14) . . ? C10' C11' H11D 119.7 . . ? C12' C11' H11D 119.7 . . ? C13' C12' C11' 121.02(15) . . ? C13' C12' H12D 119.5 . . ? C11' C12' H12D 119.5 . . ? C14' C13' C12' 118.73(15) . . ? C14' C13' H13D 120.6 . . ? C12' C13' H13D 120.6 . . ? C13' C14' C15' 120.56(17) . . ? C13' C14' H14D 119.7 . . ? C15' C14' H14D 119.7 . . ? C10' C15' C14' 121.54(16) . . ? C10' C15' H15D 119.2 . . ? C14' C15' H15D 119.2 . . ? O2' C16' N2' 122.98(11) . . ? O2' C16' C9' 121.64(11) . . ? N2' C16' C9' 115.35(12) . . ? N2' C17' C18' 112.48(10) . . ? N2' C17' C25' 112.74(11) . . ? C18' C17' C25' 111.66(11) . . ? N2' C17' H17D 106.5 . . ? C18' C17' H17D 106.5 . . ? C25' C17' H17D 106.5 . . ? C19' C18' C17' 114.42(11) . . ? C19' C18' H18D 108.7 . . ? C17' C18' H18D 108.7 . . ? C19' C18' H18E 108.7 . . ? C17' C18' H18E 108.7 . . ? H18D C18' H18E 107.6 . . ? C24' C19' C20' 118.49(13) . . ? C24' C19' C18' 121.28(13) . . ? C20' C19' C18' 120.14(12) . . ? C21' C20' C19' 120.94(14) . . ? C21' C20' H20D 119.5 . . ? C19' C20' H20D 119.5 . . ? C22' C21' C20' 119.94(14) . . ? C22' C21' H21D 120.0 . . ? C20' C21' H21D 120.0 . . ? C23' C22' C21' 119.73(15) . . ? C23' C22' H22D 120.1 . . ? C21' C22' H22D 120.1 . . ? C22' C23' C24' 120.24(14) . . ? C22' C23' H23D 119.9 . . ? C24' C23' H23D 119.9 . . ? C19' C24' C23' 120.64(14) . . ? C19' C24' H24D 119.7 . . ? C23' C24' H24D 119.7 . . ? O3' C25' N3' 123.46(13) . . ? O3' C25' C17' 119.87(12) . . ? N3' C25' C17' 116.47(12) . . ? N3' C26' H26D 109.5 . . ? N3' C26' H26E 109.5 . . ? H26D C26' H26E 109.5 . . ? N3' C26' H26F 109.5 . . ? H26D C26' H26F 109.5 . . ? H26E C26' H26F 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 C6 N1 C5 O1 178.11(13) . . . . ? C9 N1 C5 O1 -3.92(17) . . . . ? C6 N1 C5 C4 -3.2(2) . . . . ? C9 N1 C5 C4 174.72(12) . . . . ? C1 C4 C5 O1 5.88(18) . . . . ? C3 C4 C5 O1 124.68(14) . . . . ? C2 C4 C5 O1 -111.98(15) . . . . ? C1 C4 C5 N1 -172.73(12) . . . . ? C3 C4 C5 N1 -53.94(17) . . . . ? C2 C4 C5 N1 69.41(17) . . . . ? C5 N1 C6 C7 -163.72(13) . . . . ? C9 N1 C6 C7 18.21(15) . . . . ? N1 C6 C7 C8 -37.52(15) . . . . ? C6 C7 C8 C10 169.38(12) . . . . ? C6 C7 C8 C9 42.70(14) . . . . ? C5 N1 C9 C16 -52.52(15) . . . . ? C6 N1 C9 C16 125.82(12) . . . . ? C5 N1 C9 C8 -170.03(11) . . . . ? C6 N1 C9 C8 8.31(14) . . . . ? C10 C8 C9 N1 -157.92(10) . . . . ? C7 C8 C9 N1 -31.11(13) . . . . ? C10 C8 C9 C16 84.24(14) . . . . ? C7 C8 C9 C16 -148.94(11) . . . . ? C7 C8 C10 C15 131.26(13) . . . . ? C9 C8 C10 C15 -109.41(14) . . . . ? C7 C8 C10 C11 -46.70(19) . . . . ? C9 C8 C10 C11 72.64(17) . . . . ? C15 C10 C11 C12 -2.1(2) . . . . ? C8 C10 C11 C12 175.91(13) . . . . ? C10 C11 C12 C13 1.3(2) . . . . ? C11 C12 C13 C14 0.7(2) . . . . ? C12 C13 C14 C15 -1.8(2) . . . . ? C13 C14 C15 C10 1.0(2) . . . . ? C11 C10 C15 C14 0.91(19) . . . . ? C8 C10 C15 C14 -177.14(12) . . . . ? C17 N2 C16 O2 1.62(19) . . . . ? C17 N2 C16 C9 179.07(11) . . . . ? N1 C9 C16 O2 -50.27(16) . . . . ? C8 C9 C16 O2 62.72(15) . . . . ? N1 C9 C16 N2 132.21(11) . . . . ? C8 C9 C16 N2 -114.80(12) . . . . ? C16 N2 C17 C25 63.56(16) . . . . ? C16 N2 C17 C18 -66.42(16) . . . . ? N2 C17 C18 C19 -90.17(14) . . . . ? C25 C17 C18 C19 138.60(12) . . . . ? C17 C18 C19 C24 94.09(16) . . . . ? C17 C18 C19 C20 -87.63(16) . . . . ? C24 C19 C20 C21 0.4(2) . . . . ? C18 C19 C20 C21 -178.00(14) . . . . ? C19 C20 C21 C22 0.6(2) . . . . ? C20 C21 C22 C23 -1.1(2) . . . . ? C21 C22 C23 C24 0.7(3) . . . . ? C22 C23 C24 C19 0.3(3) . . . . ? C20 C19 C24 C23 -0.8(2) . . . . ? C18 C19 C24 C23 177.56(14) . . . . ? C26 N3 C25 O3 3.9(2) . . . . ? C26 N3 C25 C17 178.02(12) . . . . ? N2 C17 C25 O3 -166.23(12) . . . . ? C18 C17 C25 O3 -35.48(18) . . . . ? N2 C17 C25 N3 19.44(17) . . . . ? C18 C17 C25 N3 150.20(12) . . . . ? C9' N1' C5' O1' -3.50(17) . . . . ? C6' N1' C5' O1' 171.54(12) . . . . ? C9' N1' C5' C4' 174.82(11) . . . . ? C6' N1' C5' C4' -10.1(2) . . . . ? C3' C4' C5' O1' 127.23(14) . . . . ? C1' C4' C5' O1' 8.20(18) . . . . ? C2' C4' C5' O1' -109.62(14) . . . . ? C3' C4' C5' N1' -51.05(17) . . . . ? C1' C4' C5' N1' -170.08(12) . . . . ? C2' C4' C5' N1' 72.10(16) . . . . ? C5' N1' C6' C7' -157.45(13) . . . . ? C9' N1' C6' C7' 17.84(14) . . . . ? N1' C6' C7' C8' -37.35(13) . . . . ? C6' C7' C8' C10' 171.01(11) . . . . ? C6' C7' C8' C9' 42.87(13) . . . . ? C5' N1' C9' C16' -55.99(14) . . . . ? C6' N1' C9' C16' 128.05(11) . . . . ? C5' N1' C9' C8' -175.09(11) . . . . ? C6' N1' C9' C8' 8.95(14) . . . . ? C10' C8' C9' N1' -156.88(11) . . . . ? C7' C8' C9' N1' -31.39(12) . . . . ? C10' C8' C9' C16' 84.86(14) . . . . ? C7' C8' C9' C16' -149.65(11) . . . . ? C7' C8' C10' C15' 88.85(16) . . . . ? C9' C8' C10' C15' -152.21(14) . . . . ? C7' C8' C10' C11' -88.26(16) . . . . ? C9' C8' C10' C11' 30.68(19) . . . . ? C15' C10' C11' C12' 0.1(2) . . . . ? C8' C10' C11' C12' 177.19(13) . . . . ? C10' C11' C12' C13' -1.2(2) . . . . ? C11' C12' C13' C14' 1.0(2) . . . . ? C12' C13' C14' C15' 0.2(3) . . . . ? C11' C10' C15' C14' 1.2(2) . . . . ? C8' C10' C15' C14' -176.14(16) . . . . ? C13' C14' C15' C10' -1.3(3) . . . . ? C17' N2' C16' O2' 2.24(18) . . . . ? C17' N2' C16' C9' -179.70(11) . . . . ? N1' C9' C16' O2' -46.92(16) . . . . ? C8' C9' C16' O2' 67.30(15) . . . . ? N1' C9' C16' N2' 134.99(11) . . . . ? C8' C9' C16' N2' -110.79(12) . . . . ? C16' N2' C17' C18' -67.40(15) . . . . ? C16' N2' C17' C25' 59.95(15) . . . . ? N2' C17' C18' C19' -73.77(15) . . . . ? C25' C17' C18' C19' 158.31(11) . . . . ? C17' C18' C19' C24' 89.82(16) . . . . ? C17' C18' C19' C20' -93.65(15) . . . . ? C24' C19' C20' C21' 1.3(2) . . . . ? C18' C19' C20' C21' -175.33(14) . . . . ? C19' C20' C21' C22' -0.8(2) . . . . ? C20' C21' C22' C23' -0.1(2) . . . . ? C21' C22' C23' C24' 0.6(2) . . . . ? C20' C19' C24' C23' -0.8(2) . . . . ? C18' C19' C24' C23' 175.79(13) . . . . ? C22' C23' C24' C19' -0.2(2) . . . . ? C26' N3' C25' O3' 6.7(2) . . . . ? C26' N3' C25' C17' -178.56(12) . . . . ? N2' C17' C25' O3' -160.39(12) . . . . ? C18' C17' C25' O3' -32.61(18) . . . . ? N2' C17' C25' N3' 24.62(17) . . . . ? C18' C17' C25' N3' 152.40(12) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3 O1 0.88 2.03 2.8848(15) 161.3 . N3' H3' O1' 0.88 2.05 2.8773(14) 156.5 . N2' H2' O2 0.84 2.31 3.1352(14) 169.3 . N2 H2 O2' 0.87 2.17 3.0319(13) 167.4 1_455 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.143 _refine_diff_density_min -0.178 _refine_diff_density_rms 0.033 # Attachment '4.cif' data_Piv-(S,R)-(betaPh)Pro-D-Phe-NHMe_compound_4 _database_code_depnum_ccdc_archive 'CCDC 842884' #TrackingRef '4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '(2S,3R)-N-(tert-butylcarbonyl)-3-phenylprolyl-(R)-N'-methylphenylalaninamide' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H33 N3 O3' _chemical_formula_sum 'C26 H33 N3 O3' _chemical_formula_weight 435.55 _chemical_absolute_configuration syn 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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.6700(3) _cell_length_b 12.4890(5) _cell_length_c 19.8078(7) _cell_angle_alpha 90.00 _cell_angle_beta 93.060(3) _cell_angle_gamma 90.00 _cell_volume 2388.77(15) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.211 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.78435 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Xcalibur, Sapphire3' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17815 _diffrn_reflns_av_R_equivalents 0.0378 _diffrn_reflns_av_sigmaI/netI 0.0764 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 26.50 _reflns_number_total 9060 _reflns_number_gt 6679 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0342P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0037(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 9060 _refine_ls_number_parameters 580 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0856 _refine_ls_R_factor_gt 0.0546 _refine_ls_wR_factor_ref 0.1037 _refine_ls_wR_factor_gt 0.0912 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 O1 O 0.70025(17) -0.06511(16) 0.82621(9) 0.0313(5) Uani 1 1 d . . . O2 O 0.42451(15) 0.04265(16) 0.73809(9) 0.0290(4) Uani 1 1 d . . . O3 O 0.4587(2) 0.27664(19) 0.88894(9) 0.0483(6) Uani 1 1 d . . . N1 N 0.6220(2) -0.13576(19) 0.72865(11) 0.0279(5) Uani 1 1 d . . . N2 N 0.61815(19) 0.14415(17) 0.74981(10) 0.0216(5) Uani 1 1 d . . . H2 H 0.7111 0.1450 0.7403 0.026 Uiso 1 1 d R . . N3 N 0.5617(2) 0.1156(2) 0.88262(10) 0.0303(6) Uani 1 1 d . . . H3 H 0.6062 0.0637 0.8528 0.036 Uiso 1 1 d R . . C1 C 0.5128(3) -0.3086(3) 0.81770(18) 0.0601(10) Uani 1 1 d . . . H1A H 0.4988 -0.3229 0.7692 0.090 Uiso 1 1 calc R . . H1B H 0.4385 -0.2621 0.8324 0.090 Uiso 1 1 calc R . . H1C H 0.5116 -0.3763 0.8427 0.090 Uiso 1 1 calc R . . C2 C 0.6704(4) -0.2323(3) 0.90711(16) 0.0581(10) Uani 1 1 d . . . H2A H 0.7595 -0.1968 0.9171 0.087 Uiso 1 1 calc R . . H2B H 0.6684 -0.3004 0.9317 0.087 Uiso 1 1 calc R . . H2C H 0.5953 -0.1862 0.9213 0.087 Uiso 1 1 calc R . . C3 C 0.7688(4) -0.3276(3) 0.81085(19) 0.0674(11) Uani 1 1 d . . . H3A H 0.8583 -0.2923 0.8203 0.101 Uiso 1 1 calc R . . H3B H 0.7570 -0.3434 0.7624 0.101 Uiso 1 1 calc R . . H3C H 0.7660 -0.3945 0.8366 0.101 Uiso 1 1 calc R . . C4 C 0.6519(3) -0.2536(3) 0.83153(15) 0.0377(7) Uani 1 1 d . . . C5 C 0.6596(2) -0.1457(2) 0.79502(14) 0.0275(6) Uani 1 1 d . . . C6 C 0.5903(3) -0.2190(3) 0.67659(14) 0.0407(8) Uani 1 1 d . . . H6A H 0.4914 -0.2399 0.6756 0.049 Uiso 1 1 calc R . . H6B H 0.6484 -0.2835 0.6848 0.049 Uiso 1 1 calc R . . C7 C 0.6251(3) -0.1633(3) 0.61141(15) 0.0407(8) Uani 1 1 d . . . H7A H 0.7256 -0.1666 0.6044 0.049 Uiso 1 1 calc R . . H7B H 0.5735 -0.1950 0.5718 0.049 Uiso 1 1 calc R . . C8 C 0.5786(3) -0.0490(2) 0.62394(13) 0.0304(7) Uani 1 1 d . . . H8A H 0.4752 -0.0498 0.6241 0.036 Uiso 1 1 calc R . . C9 C 0.6337(2) -0.0298(2) 0.69698(12) 0.0239(6) Uani 1 1 d . . . H9A H 0.7332 -0.0077 0.6976 0.029 Uiso 1 1 calc R . . C10 C 0.6184(2) 0.0399(3) 0.57703(13) 0.0312(7) Uani 1 1 d . . . C11 C 0.7344(3) 0.0347(3) 0.53921(14) 0.0411(8) Uani 1 1 d . . . H11A H 0.7888 -0.0287 0.5402 0.049 Uiso 1 1 calc R . . C12 C 0.7725(3) 0.1206(3) 0.49991(15) 0.0524(10) Uani 1 1 d . . . H12A H 0.8515 0.1155 0.4736 0.063 Uiso 1 1 calc R . . C13 C 0.6954(3) 0.2131(3) 0.49917(15) 0.0524(10) Uani 1 1 d . . . H13A H 0.7220 0.2723 0.4727 0.063 Uiso 1 1 calc R . . C14 C 0.5805(3) 0.2204(3) 0.53639(14) 0.0468(9) Uani 1 1 d . . . H14A H 0.5277 0.2846 0.5360 0.056 Uiso 1 1 calc R . . C15 C 0.5417(3) 0.1336(3) 0.57458(13) 0.0373(8) Uani 1 1 d . . . H15A H 0.4609 0.1385 0.5996 0.045 Uiso 1 1 calc R . . C16 C 0.5493(2) 0.0555(2) 0.73101(12) 0.0229(6) Uani 1 1 d . . . C17 C 0.5534(2) 0.2338(2) 0.78353(12) 0.0248(6) Uani 1 1 d . . . H17A H 0.4645 0.2509 0.7577 0.030 Uiso 1 1 calc R . . C18 C 0.6469(3) 0.3325(2) 0.78167(13) 0.0314(7) Uani 1 1 d . . . H18A H 0.6132 0.3861 0.8137 0.038 Uiso 1 1 calc R . . H18B H 0.7415 0.3114 0.7981 0.038 Uiso 1 1 calc R . . C19 C 0.6561(3) 0.3855(2) 0.71362(14) 0.0299(7) Uani 1 1 d . . . C20 C 0.7750(3) 0.3802(3) 0.67779(15) 0.0437(8) Uani 1 1 d . . . H20A H 0.8515 0.3392 0.6953 0.052 Uiso 1 1 calc R . . C21 C 0.7845(3) 0.4333(3) 0.61716(17) 0.0526(9) Uani 1 1 d . . . H21A H 0.8669 0.4280 0.5934 0.063 Uiso 1 1 calc R . . C22 C 0.6754(3) 0.4940(3) 0.59073(16) 0.0491(9) Uani 1 1 d . . . H22A H 0.6829 0.5320 0.5495 0.059 Uiso 1 1 calc R . . C23 C 0.5557(3) 0.4987(3) 0.62494(16) 0.0453(8) Uani 1 1 d . . . H23A H 0.4790 0.5391 0.6069 0.054 Uiso 1 1 calc R . . C24 C 0.5461(3) 0.4447(3) 0.68586(15) 0.0381(8) Uani 1 1 d . . . H24A H 0.4626 0.4484 0.7089 0.046 Uiso 1 1 calc R . . C25 C 0.5198(2) 0.2091(2) 0.85713(13) 0.0282(6) Uani 1 1 d . . . C26 C 0.5267(3) 0.0814(3) 0.94962(14) 0.0475(9) Uani 1 1 d . . . H26A H 0.6039 0.0975 0.9821 0.071 Uiso 1 1 calc R . . H26B H 0.5088 0.0042 0.9493 0.071 Uiso 1 1 calc R . . H26C H 0.4436 0.1196 0.9627 0.071 Uiso 1 1 calc R . . O1' O 1.20865(17) 0.29244(15) 0.77499(9) 0.0287(4) Uani 1 1 d . . . O2' O 0.92293(16) 0.14459(16) 0.73974(8) 0.0312(5) Uani 1 1 d . . . O3' O 1.1200(2) 0.1715(2) 0.53424(10) 0.0512(6) Uani 1 1 d . . . N1' N 1.0916(2) 0.22193(19) 0.85794(10) 0.0253(5) Uani 1 1 d . . . N2' N 1.12782(19) 0.07897(19) 0.70798(9) 0.0239(5) Uani 1 1 d . . . H2' H 1.2207 0.0748 0.7187 0.029 Uiso 1 1 d R . . N3' N 1.1668(2) 0.2584(2) 0.63277(11) 0.0363(6) Uani 1 1 d . . . H3' H 1.1647 0.2549 0.6806 0.044 Uiso 1 1 d R . . C1' C 1.0102(3) 0.4695(3) 0.84600(15) 0.0398(7) Uani 1 1 d . . . H1D H 1.0088 0.5411 0.8662 0.060 Uiso 1 1 calc R . . H1E H 0.9385 0.4251 0.8651 0.060 Uiso 1 1 calc R . . H1F H 0.9924 0.4752 0.7970 0.060 Uiso 1 1 calc R . . C2' C 1.2602(3) 0.4853(3) 0.82639(16) 0.0413(8) Uani 1 1 d . . . H2D H 1.3522 0.4538 0.8353 0.062 Uiso 1 1 calc R . . H2E H 1.2597 0.5586 0.8441 0.062 Uiso 1 1 calc R . . H2F H 1.2380 0.4866 0.7775 0.062 Uiso 1 1 calc R . . C3' C 1.1911(3) 0.4188(3) 0.93697(14) 0.0459(8) Uani 1 1 d . . . H3D H 1.2827 0.3862 0.9451 0.069 Uiso 1 1 calc R . . H3E H 1.1224 0.3778 0.9608 0.069 Uiso 1 1 calc R . . H3F H 1.1932 0.4927 0.9536 0.069 Uiso 1 1 calc R . . C4' C 1.1521(3) 0.4183(2) 0.86114(14) 0.0316(7) Uani 1 1 d . . . C5' C 1.1537(2) 0.3058(2) 0.82908(13) 0.0242(6) Uani 1 1 d . . . C6' C 1.0069(3) 0.2186(3) 0.91714(14) 0.0395(8) Uani 1 1 d . . . H6D H 0.9442 0.2813 0.9180 0.047 Uiso 1 1 calc R . . H6E H 1.0656 0.2168 0.9596 0.047 Uiso 1 1 calc R . . C7' C 0.9258(3) 0.1157(3) 0.90721(16) 0.0444(8) Uani 1 1 d . . . H7D H 0.8385 0.1287 0.8800 0.053 Uiso 1 1 calc R . . H7E H 0.9029 0.0851 0.9514 0.053 Uiso 1 1 calc R . . C8' C 1.0192(2) 0.0399(2) 0.87026(13) 0.0303(7) Uani 1 1 d . . . H8D H 0.9593 -0.0056 0.8392 0.036 Uiso 1 1 calc R . . C9' C 1.1038(2) 0.1161(2) 0.82649(12) 0.0230(6) Uani 1 1 d . . . H9D H 1.2030 0.0932 0.8278 0.028 Uiso 1 1 calc R . . C10' C 1.1093(3) -0.0336(2) 0.91472(13) 0.0312(7) Uani 1 1 d . . . C11' C 1.1708(3) -0.0013(3) 0.97625(18) 0.0576(10) Uani 1 1 d . . . H11D H 1.1542 0.0691 0.9921 0.069 Uiso 1 1 calc R . . C12' C 1.2558(3) -0.0691(3) 1.01509(19) 0.0612(11) Uani 1 1 d . . . H12D H 1.2976 -0.0447 1.0568 0.073 Uiso 1 1 calc R . . C13' C 1.2792(4) -0.1697(4) 0.99384(19) 0.0672(12) Uani 1 1 d . . . H13D H 1.3390 -0.2158 1.0200 0.081 Uiso 1 1 calc R . . C14' C 1.2176(5) -0.2044(4) 0.9356(2) 0.1015(18) Uani 1 1 d . . . H14D H 1.2320 -0.2759 0.9212 0.122 Uiso 1 1 calc R . . C15' C 1.1323(5) -0.1361(3) 0.89575(17) 0.0764(13) Uani 1 1 d . . . H15D H 1.0897 -0.1621 0.8546 0.092 Uiso 1 1 calc R . . C16' C 1.0433(2) 0.1166(2) 0.75379(12) 0.0223(6) Uani 1 1 d . . . C17' C 1.0898(2) 0.0724(2) 0.63604(12) 0.0277(7) Uani 1 1 d . . . H17D H 0.9871 0.0629 0.6309 0.033 Uiso 1 1 calc R . . C18' C 1.1573(3) -0.0257(3) 0.60455(13) 0.0331(7) Uani 1 1 d . . . H18D H 1.1333 -0.0256 0.5553 0.040 Uiso 1 1 calc R . . H18E H 1.2591 -0.0182 0.6107 0.040 Uiso 1 1 calc R . . C19' C 1.1163(3) -0.1326(3) 0.63313(13) 0.0295(7) Uani 1 1 d . . . C20' C 1.1792(3) -0.1716(3) 0.69263(15) 0.0429(8) Uani 1 1 d . . . H20D H 1.2482 -0.1302 0.7165 0.052 Uiso 1 1 calc R . . C21' C 1.1425(3) -0.2702(3) 0.71754(16) 0.0508(9) Uani 1 1 d . . . H21D H 1.1869 -0.2961 0.7582 0.061 Uiso 1 1 calc R . . C22' C 1.0414(3) -0.3321(3) 0.68392(15) 0.0462(8) Uani 1 1 d . . . H22D H 1.0156 -0.3996 0.7015 0.055 Uiso 1 1 calc R . . C23' C 0.9790(3) -0.2934(3) 0.62423(15) 0.0397(8) Uani 1 1 d . . . H23D H 0.9098 -0.3346 0.6003 0.048 Uiso 1 1 calc R . . C24' C 1.0171(3) -0.1952(3) 0.59960(13) 0.0330(7) Uani 1 1 d . . . H24D H 0.9740 -0.1699 0.5584 0.040 Uiso 1 1 calc R . . C25' C 1.1273(3) 0.1730(3) 0.59624(14) 0.0331(7) Uani 1 1 d . . . C26' C 1.1998(3) 0.3592(3) 0.59973(16) 0.0513(9) Uani 1 1 d . . . H26D H 1.2823 0.3496 0.5737 0.077 Uiso 1 1 calc R . . H26E H 1.2175 0.4147 0.6341 0.077 Uiso 1 1 calc R . . H26F H 1.1216 0.3808 0.5692 0.077 Uiso 1 1 calc 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 O1 0.0325(10) 0.0262(13) 0.0348(11) 0.0018(9) -0.0018(8) 0.0016(9) O2 0.0181(9) 0.0312(12) 0.0376(11) -0.0021(9) 0.0013(7) -0.0031(8) O3 0.0566(12) 0.0531(16) 0.0352(12) -0.0043(11) 0.0042(10) 0.0279(12) N1 0.0258(11) 0.0214(14) 0.0364(14) -0.0009(11) 0.0006(10) -0.0020(10) N2 0.0175(10) 0.0209(14) 0.0267(12) -0.0016(10) 0.0036(8) -0.0007(9) N3 0.0344(12) 0.0302(15) 0.0268(12) 0.0011(11) 0.0052(10) 0.0030(11) C1 0.054(2) 0.048(3) 0.078(3) 0.013(2) 0.0064(18) -0.0198(18) C2 0.075(2) 0.049(3) 0.050(2) 0.0237(19) -0.0016(17) -0.007(2) C3 0.065(2) 0.048(3) 0.091(3) 0.025(2) 0.018(2) 0.025(2) C4 0.0343(15) 0.0295(19) 0.049(2) 0.0072(15) 0.0031(13) 0.0010(14) C5 0.0189(13) 0.0256(18) 0.0380(17) 0.0008(14) 0.0032(11) 0.0013(12) C6 0.0411(17) 0.0275(19) 0.053(2) -0.0139(16) -0.0024(14) -0.0026(14) C7 0.0425(17) 0.039(2) 0.0401(18) -0.0124(16) 0.0000(13) -0.0004(15) C8 0.0242(13) 0.0364(19) 0.0305(15) -0.0065(14) 0.0010(11) 0.0024(12) C9 0.0187(12) 0.0246(16) 0.0286(14) -0.0003(13) 0.0035(10) -0.0030(11) C10 0.0250(13) 0.044(2) 0.0237(15) -0.0076(14) -0.0045(11) -0.0013(13) C11 0.0378(16) 0.052(2) 0.0339(17) -0.0061(16) 0.0063(13) 0.0028(16) C12 0.0443(18) 0.077(3) 0.0371(18) 0.001(2) 0.0142(15) -0.008(2) C13 0.061(2) 0.061(3) 0.0351(18) 0.0128(19) 0.0042(16) -0.009(2) C14 0.0539(19) 0.052(2) 0.0346(17) 0.0086(17) 0.0006(14) 0.0068(17) C15 0.0347(15) 0.048(2) 0.0296(16) 0.0039(15) 0.0041(12) 0.0023(15) C16 0.0202(13) 0.0259(17) 0.0223(14) 0.0014(12) -0.0017(10) 0.0017(11) C17 0.0234(13) 0.0225(17) 0.0281(14) -0.0016(12) -0.0015(11) 0.0062(11) C18 0.0340(15) 0.0224(17) 0.0370(16) -0.0028(13) -0.0061(12) -0.0019(12) C19 0.0311(15) 0.0209(17) 0.0375(16) -0.0049(13) 0.0001(12) -0.0042(12) C20 0.0353(16) 0.045(2) 0.050(2) 0.0044(17) -0.0005(14) 0.0016(15) C21 0.0472(18) 0.056(3) 0.055(2) 0.0082(19) 0.0104(16) -0.0073(18) C22 0.060(2) 0.042(2) 0.0446(19) 0.0114(17) 0.0008(16) -0.0123(18) C23 0.0505(18) 0.033(2) 0.051(2) 0.0046(16) -0.0114(16) 0.0032(16) C24 0.0388(16) 0.033(2) 0.0423(18) 0.0004(15) -0.0007(14) 0.0004(14) C25 0.0213(13) 0.0321(18) 0.0307(15) -0.0067(14) -0.0010(11) 0.0035(12) C26 0.066(2) 0.043(2) 0.0344(17) 0.0057(16) 0.0147(15) -0.0045(18) O1' 0.0334(9) 0.0267(12) 0.0265(10) -0.0034(9) 0.0060(8) -0.0055(9) O2' 0.0207(9) 0.0375(13) 0.0350(10) 0.0028(9) -0.0020(7) 0.0028(9) O3' 0.0665(14) 0.0602(18) 0.0258(11) 0.0070(11) -0.0069(10) -0.0086(13) N1' 0.0253(11) 0.0271(14) 0.0240(12) -0.0008(10) 0.0066(9) 0.0000(10) N2' 0.0173(10) 0.0292(14) 0.0249(12) 0.0006(10) -0.0009(9) 0.0015(10) N3' 0.0443(14) 0.0367(17) 0.0277(13) 0.0055(12) -0.0015(11) -0.0111(12) C1' 0.0346(15) 0.0314(19) 0.0532(19) 0.0005(16) 0.0008(13) 0.0087(14) C2' 0.0376(16) 0.0235(18) 0.063(2) -0.0050(16) 0.0071(14) -0.0026(14) C3' 0.0464(17) 0.048(2) 0.0429(19) -0.0157(17) -0.0035(14) 0.0116(17) C4' 0.0306(14) 0.0292(18) 0.0348(16) -0.0050(14) -0.0004(12) 0.0087(13) C5' 0.0216(13) 0.0260(17) 0.0245(15) 0.0001(12) -0.0020(11) 0.0030(12) C6' 0.0420(16) 0.044(2) 0.0343(16) 0.0060(15) 0.0179(13) 0.0131(15) C7' 0.0306(15) 0.054(2) 0.0507(19) 0.0198(18) 0.0172(13) 0.0073(15) C8' 0.0255(13) 0.0315(18) 0.0333(16) 0.0085(14) -0.0031(11) -0.0092(13) C9' 0.0189(12) 0.0240(16) 0.0261(14) 0.0021(12) -0.0003(10) -0.0002(11) C10' 0.0293(14) 0.0311(19) 0.0340(16) 0.0121(14) 0.0078(12) -0.0036(13) C11' 0.067(2) 0.036(2) 0.065(2) 0.0083(19) -0.0305(18) -0.0041(18) C12' 0.047(2) 0.069(3) 0.065(2) 0.025(2) -0.0173(17) -0.008(2) C13' 0.062(2) 0.086(4) 0.055(3) 0.033(2) 0.0190(19) 0.033(2) C14' 0.176(5) 0.069(4) 0.059(3) 0.003(2) 0.008(3) 0.072(3) C15' 0.136(4) 0.055(3) 0.037(2) -0.010(2) -0.008(2) 0.037(3) C16' 0.0182(13) 0.0196(15) 0.0289(14) 0.0020(12) -0.0012(11) -0.0024(11) C17' 0.0219(13) 0.0383(19) 0.0226(14) -0.0031(13) -0.0032(10) -0.0022(12) C18' 0.0272(14) 0.044(2) 0.0278(15) -0.0086(15) 0.0030(11) -0.0001(14) C19' 0.0269(14) 0.0368(19) 0.0249(15) -0.0084(14) 0.0028(11) 0.0024(13) C20' 0.0468(18) 0.038(2) 0.0423(19) -0.0075(16) -0.0127(15) 0.0032(15) C21' 0.070(2) 0.044(2) 0.0367(18) -0.0006(17) -0.0104(16) 0.0049(19) C22' 0.061(2) 0.036(2) 0.0420(19) -0.0018(17) 0.0087(16) -0.0007(17) C23' 0.0370(16) 0.041(2) 0.0418(18) -0.0084(16) 0.0059(14) -0.0013(14) C24' 0.0313(14) 0.040(2) 0.0272(15) -0.0048(14) -0.0009(12) 0.0013(14) C25' 0.0290(15) 0.042(2) 0.0274(16) 0.0030(14) -0.0030(12) -0.0031(14) C26' 0.062(2) 0.046(2) 0.0449(19) 0.0108(17) -0.0031(15) -0.0168(18) _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 O1 C5 1.234(3) . ? O2 C16 1.233(3) . ? O3 C25 1.223(3) . ? N1 C5 1.351(3) . ? N1 C9 1.471(3) . ? N1 C6 1.485(3) . ? N2 C16 1.335(3) . ? N2 C17 1.461(3) . ? N2 H2 0.9277 . ? N3 C25 1.327(4) . ? N3 C26 1.451(3) . ? N3 H3 0.9908 . ? C1 C4 1.522(4) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C4 1.522(4) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.534(4) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C5 1.533(4) . ? C6 C7 1.520(4) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.520(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C10 1.511(4) . ? C8 C9 1.534(3) . ? C8 H8A 1.0000 . ? C9 C16 1.521(4) . ? C9 H9A 1.0000 . ? C10 C11 1.383(4) . ? C10 C15 1.385(4) . ? C11 C12 1.387(5) . ? C11 H11A 0.9500 . ? C12 C13 1.375(5) . ? C12 H12A 0.9500 . ? C13 C14 1.369(4) . ? C13 H13A 0.9500 . ? C14 C15 1.385(4) . ? C14 H14A 0.9500 . ? C15 H15A 0.9500 . ? C17 C18 1.531(4) . ? C17 C25 1.541(3) . ? C17 H17A 1.0000 . ? C18 C19 1.509(4) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C24 1.384(4) . ? C19 C20 1.385(4) . ? C20 C21 1.379(4) . ? C20 H20A 0.9500 . ? C21 C22 1.380(5) . ? C21 H21A 0.9500 . ? C22 C23 1.374(4) . ? C22 H22A 0.9500 . ? C23 C24 1.390(4) . ? C23 H23A 0.9500 . ? C24 H24A 0.9500 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? O1' C5' 1.232(3) . ? O2' C16' 1.233(3) . ? O3' C25' 1.227(3) . ? N1' C5' 1.350(3) . ? N1' C6' 1.467(3) . ? N1' C9' 1.469(3) . ? N2' C16' 1.339(3) . ? N2' C17' 1.455(3) . ? N2' H2' 0.9130 . ? N3' C25' 1.333(4) . ? N3' C26' 1.462(4) . ? N3' H3' 0.9490 . ? C1' C4' 1.529(4) . ? C1' H1D 0.9800 . ? C1' H1E 0.9800 . ? C1' H1F 0.9800 . ? C2' C4' 1.531(4) . ? C2' H2D 0.9800 . ? C2' H2E 0.9800 . ? C2' H2F 0.9800 . ? C3' C4' 1.529(4) . ? C3' H3D 0.9800 . ? C3' H3E 0.9800 . ? C3' H3F 0.9800 . ? C4' C5' 1.542(4) . ? C6' C7' 1.513(4) . ? C6' H6D 0.9900 . ? C6' H6E 0.9900 . ? C7' C8' 1.523(4) . ? C7' H7D 0.9900 . ? C7' H7E 0.9900 . ? C8' C10' 1.515(4) . ? C8' C9' 1.550(3) . ? C8' H8D 1.0000 . ? C9' C16' 1.525(3) . ? C9' H9D 1.0000 . ? C10' C15' 1.356(5) . ? C10' C11' 1.387(4) . ? C11' C12' 1.385(5) . ? C11' H11D 0.9500 . ? C12' C13' 1.348(6) . ? C12' H12D 0.9500 . ? C13' C14' 1.342(6) . ? C13' H13D 0.9500 . ? C14' C15' 1.400(5) . ? C14' H14D 0.9500 . ? C15' H15D 0.9500 . ? C17' C18' 1.536(4) . ? C17' C25' 1.537(4) . ? C17' H17D 1.0000 . ? C18' C19' 1.511(4) . ? C18' H18D 0.9900 . ? C18' H18E 0.9900 . ? C19' C24' 1.380(4) . ? C19' C20' 1.386(4) . ? C20' C21' 1.380(5) . ? C20' H20D 0.9500 . ? C21' C22' 1.387(4) . ? C21' H21D 0.9500 . ? C22' C23' 1.386(4) . ? C22' H22D 0.9500 . ? C23' C24' 1.378(4) . ? C23' H23D 0.9500 . ? C24' H24D 0.9500 . ? C26' H26D 0.9800 . ? C26' H26E 0.9800 . ? C26' H26F 0.9800 . ? 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 C5 N1 C9 118.3(2) . . ? C5 N1 C6 130.3(2) . . ? C9 N1 C6 110.6(2) . . ? C16 N2 C17 122.92(19) . . ? C16 N2 H2 115.2 . . ? C17 N2 H2 121.8 . . ? C25 N3 C26 121.7(2) . . ? C25 N3 H3 118.9 . . ? C26 N3 H3 118.9 . . ? C4 C1 H1A 109.5 . . ? C4 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C4 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C4 C2 H2A 109.5 . . ? C4 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C4 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C4 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C2 C4 C1 108.2(3) . . ? C2 C4 C5 107.8(3) . . ? C1 C4 C5 112.1(2) . . ? C2 C4 C3 108.5(3) . . ? C1 C4 C3 109.7(3) . . ? C5 C4 C3 110.4(2) . . ? O1 C5 N1 118.3(3) . . ? O1 C5 C4 120.2(2) . . ? N1 C5 C4 121.5(3) . . ? N1 C6 C7 102.8(2) . . ? N1 C6 H6A 111.2 . . ? C7 C6 H6A 111.2 . . ? N1 C6 H6B 111.2 . . ? C7 C6 H6B 111.2 . . ? H6A C6 H6B 109.1 . . ? C8 C7 C6 102.1(2) . . ? C8 C7 H7A 111.3 . . ? C6 C7 H7A 111.3 . . ? C8 C7 H7B 111.3 . . ? C6 C7 H7B 111.3 . . ? H7A C7 H7B 109.2 . . ? C10 C8 C7 120.1(2) . . ? C10 C8 C9 112.2(2) . . ? C7 C8 C9 102.1(2) . . ? C10 C8 H8A 107.2 . . ? C7 C8 H8A 107.2 . . ? C9 C8 H8A 107.2 . . ? N1 C9 C16 112.7(2) . . ? N1 C9 C8 103.3(2) . . ? C16 C9 C8 111.1(2) . . ? N1 C9 H9A 109.9 . . ? C16 C9 H9A 109.9 . . ? C8 C9 H9A 109.9 . . ? C11 C10 C15 117.9(3) . . ? C11 C10 C8 122.6(3) . . ? C15 C10 C8 119.3(2) . . ? C10 C11 C12 121.0(3) . . ? C10 C11 H11A 119.5 . . ? C12 C11 H11A 119.5 . . ? C13 C12 C11 119.7(3) . . ? C13 C12 H12A 120.1 . . ? C11 C12 H12A 120.1 . . ? C14 C13 C12 120.4(3) . . ? C14 C13 H13A 119.8 . . ? C12 C13 H13A 119.8 . . ? C13 C14 C15 119.6(3) . . ? C13 C14 H14A 120.2 . . ? C15 C14 H14A 120.2 . . ? C14 C15 C10 121.4(3) . . ? C14 C15 H15A 119.3 . . ? C10 C15 H15A 119.3 . . ? O2 C16 N2 123.6(2) . . ? O2 C16 C9 120.7(2) . . ? N2 C16 C9 115.7(2) . . ? N2 C17 C18 109.76(19) . . ? N2 C17 C25 113.4(2) . . ? C18 C17 C25 109.8(2) . . ? N2 C17 H17A 107.9 . . ? C18 C17 H17A 107.9 . . ? C25 C17 H17A 107.9 . . ? C19 C18 C17 116.0(2) . . ? C19 C18 H18A 108.3 . . ? C17 C18 H18A 108.3 . . ? C19 C18 H18B 108.3 . . ? C17 C18 H18B 108.3 . . ? H18A C18 H18B 107.4 . . ? C24 C19 C20 117.6(3) . . ? C24 C19 C18 120.6(2) . . ? C20 C19 C18 121.8(3) . . ? C21 C20 C19 121.2(3) . . ? C21 C20 H20A 119.4 . . ? C19 C20 H20A 119.4 . . ? C20 C21 C22 120.6(3) . . ? C20 C21 H21A 119.7 . . ? C22 C21 H21A 119.7 . . ? C23 C22 C21 118.9(3) . . ? C23 C22 H22A 120.5 . . ? C21 C22 H22A 120.5 . . ? C22 C23 C24 120.3(3) . . ? C22 C23 H23A 119.9 . . ? C24 C23 H23A 119.9 . . ? C19 C24 C23 121.3(3) . . ? C19 C24 H24A 119.4 . . ? C23 C24 H24A 119.4 . . ? O3 C25 N3 123.8(3) . . ? O3 C25 C17 118.8(3) . . ? N3 C25 C17 117.4(2) . . ? N3 C26 H26A 109.5 . . ? N3 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N3 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C5' N1' C6' 129.9(2) . . ? C5' N1' C9' 118.11(19) . . ? C6' N1' C9' 112.0(2) . . ? C16' N2' C17' 123.5(2) . . ? C16' N2' H2' 119.4 . . ? C17' N2' H2' 114.8 . . ? C25' N3' C26' 120.6(2) . . ? C25' N3' H3' 119.0 . . ? C26' N3' H3' 120.1 . . ? C4' C1' H1D 109.5 . . ? C4' C1' H1E 109.5 . . ? H1D C1' H1E 109.5 . . ? C4' C1' H1F 109.5 . . ? H1D C1' H1F 109.5 . . ? H1E C1' H1F 109.5 . . ? C4' C2' H2D 109.5 . . ? C4' C2' H2E 109.5 . . ? H2D C2' H2E 109.5 . . ? C4' C2' H2F 109.5 . . ? H2D C2' H2F 109.5 . . ? H2E C2' H2F 109.5 . . ? C4' C3' H3D 109.5 . . ? C4' C3' H3E 109.5 . . ? H3D C3' H3E 109.5 . . ? C4' C3' H3F 109.5 . . ? H3D C3' H3F 109.5 . . ? H3E C3' H3F 109.5 . . ? C3' C4' C1' 111.3(2) . . ? C3' C4' C2' 107.5(2) . . ? C1' C4' C2' 108.1(2) . . ? C3' C4' C5' 113.6(2) . . ? C1' C4' C5' 109.2(2) . . ? C2' C4' C5' 106.9(2) . . ? O1' C5' N1' 119.0(2) . . ? O1' C5' C4' 119.7(2) . . ? N1' C5' C4' 121.2(2) . . ? N1' C6' C7' 103.2(2) . . ? N1' C6' H6D 111.1 . . ? C7' C6' H6D 111.1 . . ? N1' C6' H6E 111.1 . . ? C7' C6' H6E 111.1 . . ? H6D C6' H6E 109.1 . . ? C6' C7' C8' 105.9(2) . . ? C6' C7' H7D 110.6 . . ? C8' C7' H7D 110.6 . . ? C6' C7' H7E 110.6 . . ? C8' C7' H7E 110.6 . . ? H7D C7' H7E 108.7 . . ? C10' C8' C7' 115.8(2) . . ? C10' C8' C9' 113.12(19) . . ? C7' C8' C9' 103.4(2) . . ? C10' C8' H8D 108.1 . . ? C7' C8' H8D 108.1 . . ? C9' C8' H8D 108.1 . . ? N1' C9' C16' 111.2(2) . . ? N1' C9' C8' 105.0(2) . . ? C16' C9' C8' 110.1(2) . . ? N1' C9' H9D 110.2 . . ? C16' C9' H9D 110.2 . . ? C8' C9' H9D 110.2 . . ? C15' C10' C11' 116.7(3) . . ? C15' C10' C8' 120.6(3) . . ? C11' C10' C8' 122.8(3) . . ? C12' C11' C10' 121.6(4) . . ? C12' C11' H11D 119.2 . . ? C10' C11' H11D 119.2 . . ? C13' C12' C11' 120.1(4) . . ? C13' C12' H12D 119.9 . . ? C11' C12' H12D 119.9 . . ? C14' C13' C12' 119.7(4) . . ? C14' C13' H13D 120.2 . . ? C12' C13' H13D 120.2 . . ? C13' C14' C15' 120.6(4) . . ? C13' C14' H14D 119.7 . . ? C15' C14' H14D 119.7 . . ? C10' C15' C14' 121.3(4) . . ? C10' C15' H15D 119.4 . . ? C14' C15' H15D 119.4 . . ? O2' C16' N2' 123.4(2) . . ? O2' C16' C9' 121.6(2) . . ? N2' C16' C9' 114.9(2) . . ? N2' C17' C18' 110.6(2) . . ? N2' C17' C25' 113.7(2) . . ? C18' C17' C25' 109.0(2) . . ? N2' C17' H17D 107.8 . . ? C18' C17' H17D 107.8 . . ? C25' C17' H17D 107.8 . . ? C19' C18' C17' 115.2(2) . . ? C19' C18' H18D 108.5 . . ? C17' C18' H18D 108.5 . . ? C19' C18' H18E 108.5 . . ? C17' C18' H18E 108.5 . . ? H18D C18' H18E 107.5 . . ? C24' C19' C20' 118.2(3) . . ? C24' C19' C18' 120.6(3) . . ? C20' C19' C18' 121.2(3) . . ? C21' C20' C19' 120.5(3) . . ? C21' C20' H20D 119.7 . . ? C19' C20' H20D 119.7 . . ? C20' C21' C22' 120.9(3) . . ? C20' C21' H21D 119.6 . . ? C22' C21' H21D 119.6 . . ? C23' C22' C21' 118.6(3) . . ? C23' C22' H22D 120.7 . . ? C21' C22' H22D 120.7 . . ? C24' C23' C22' 120.0(3) . . ? C24' C23' H23D 120.0 . . ? C22' C23' H23D 120.0 . . ? C23' C24' C19' 121.8(3) . . ? C23' C24' H24D 119.1 . . ? C19' C24' H24D 119.1 . . ? O3' C25' N3' 123.7(3) . . ? O3' C25' C17' 119.9(3) . . ? N3' C25' C17' 116.4(2) . . ? N3' C26' H26D 109.5 . . ? N3' C26' H26E 109.5 . . ? H26D C26' H26E 109.5 . . ? N3' C26' H26F 109.5 . . ? H26D C26' H26F 109.5 . . ? H26E C26' H26F 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 C9 N1 C5 O1 1.0(3) . . . . ? C6 N1 C5 O1 169.5(2) . . . . ? C9 N1 C5 C4 -179.3(2) . . . . ? C6 N1 C5 C4 -10.8(4) . . . . ? C2 C4 C5 O1 11.9(3) . . . . ? C1 C4 C5 O1 130.9(3) . . . . ? C3 C4 C5 O1 -106.5(3) . . . . ? C2 C4 C5 N1 -167.8(2) . . . . ? C1 C4 C5 N1 -48.8(3) . . . . ? C3 C4 C5 N1 73.8(3) . . . . ? C5 N1 C6 C7 -153.3(2) . . . . ? C9 N1 C6 C7 16.0(3) . . . . ? N1 C6 C7 C8 -36.6(3) . . . . ? C6 C7 C8 C10 168.5(2) . . . . ? C6 C7 C8 C9 43.6(2) . . . . ? C5 N1 C9 C16 -58.3(3) . . . . ? C6 N1 C9 C16 131.0(2) . . . . ? C5 N1 C9 C8 -178.3(2) . . . . ? C6 N1 C9 C8 11.0(2) . . . . ? C10 C8 C9 N1 -163.6(2) . . . . ? C7 C8 C9 N1 -33.6(2) . . . . ? C10 C8 C9 C16 75.4(3) . . . . ? C7 C8 C9 C16 -154.6(2) . . . . ? C7 C8 C10 C11 -25.3(4) . . . . ? C9 C8 C10 C11 94.6(3) . . . . ? C7 C8 C10 C15 159.0(3) . . . . ? C9 C8 C10 C15 -81.0(3) . . . . ? C15 C10 C11 C12 -0.2(4) . . . . ? C8 C10 C11 C12 -175.9(3) . . . . ? C10 C11 C12 C13 1.0(5) . . . . ? C11 C12 C13 C14 -0.7(5) . . . . ? C12 C13 C14 C15 -0.4(5) . . . . ? C13 C14 C15 C10 1.2(5) . . . . ? C11 C10 C15 C14 -0.9(4) . . . . ? C8 C10 C15 C14 174.9(3) . . . . ? C17 N2 C16 O2 2.7(4) . . . . ? C17 N2 C16 C9 -179.6(2) . . . . ? N1 C9 C16 O2 -54.5(3) . . . . ? C8 C9 C16 O2 60.9(3) . . . . ? N1 C9 C16 N2 127.7(2) . . . . ? C8 C9 C16 N2 -116.9(2) . . . . ? C16 N2 C17 C18 -165.4(2) . . . . ? C16 N2 C17 C25 71.5(3) . . . . ? N2 C17 C18 C19 71.6(3) . . . . ? C25 C17 C18 C19 -163.2(2) . . . . ? C17 C18 C19 C24 73.1(3) . . . . ? C17 C18 C19 C20 -109.2(3) . . . . ? C24 C19 C20 C21 1.0(5) . . . . ? C18 C19 C20 C21 -176.8(3) . . . . ? C19 C20 C21 C22 0.5(5) . . . . ? C20 C21 C22 C23 -1.6(5) . . . . ? C21 C22 C23 C24 1.2(5) . . . . ? C20 C19 C24 C23 -1.3(4) . . . . ? C18 C19 C24 C23 176.5(3) . . . . ? C22 C23 C24 C19 0.3(5) . . . . ? C26 N3 C25 O3 5.8(4) . . . . ? C26 N3 C25 C17 -175.5(2) . . . . ? N2 C17 C25 O3 -176.2(2) . . . . ? C18 C17 C25 O3 60.7(3) . . . . ? N2 C17 C25 N3 5.0(3) . . . . ? C18 C17 C25 N3 -118.1(3) . . . . ? C6' N1' C5' O1' -172.5(2) . . . . ? C9' N1' C5' O1' 5.6(3) . . . . ? C6' N1' C5' C4' 5.1(4) . . . . ? C9' N1' C5' C4' -176.8(2) . . . . ? C3' C4' C5' O1' -134.8(2) . . . . ? C1' C4' C5' O1' 100.3(3) . . . . ? C2' C4' C5' O1' -16.4(3) . . . . ? C3' C4' C5' N1' 47.6(3) . . . . ? C1' C4' C5' N1' -77.3(3) . . . . ? C2' C4' C5' N1' 166.0(2) . . . . ? C5' N1' C6' C7' 159.0(3) . . . . ? C9' N1' C6' C7' -19.3(3) . . . . ? N1' C6' C7' C8' 31.3(3) . . . . ? C6' C7' C8' C10' 92.8(3) . . . . ? C6' C7' C8' C9' -31.5(3) . . . . ? C5' N1' C9' C16' -59.6(3) . . . . ? C6' N1' C9' C16' 118.8(2) . . . . ? C5' N1' C9' C8' -178.6(2) . . . . ? C6' N1' C9' C8' -0.1(3) . . . . ? C10' C8' C9' N1' -106.6(3) . . . . ? C7' C8' C9' N1' 19.4(3) . . . . ? C10' C8' C9' C16' 133.7(2) . . . . ? C7' C8' C9' C16' -100.3(3) . . . . ? C7' C8' C10' C15' 141.8(3) . . . . ? C9' C8' C10' C15' -99.1(4) . . . . ? C7' C8' C10' C11' -37.5(4) . . . . ? C9' C8' C10' C11' 81.5(3) . . . . ? C15' C10' C11' C12' 2.4(5) . . . . ? C8' C10' C11' C12' -178.2(3) . . . . ? C10' C11' C12' C13' -0.8(5) . . . . ? C11' C12' C13' C14' -1.3(6) . . . . ? C12' C13' C14' C15' 1.8(7) . . . . ? C11' C10' C15' C14' -2.0(6) . . . . ? C8' C10' C15' C14' 178.7(4) . . . . ? C13' C14' C15' C10' -0.1(7) . . . . ? C17' N2' C16' O2' 3.5(4) . . . . ? C17' N2' C16' C9' 179.8(2) . . . . ? N1' C9' C16' O2' -55.9(3) . . . . ? C8' C9' C16' O2' 60.0(3) . . . . ? N1' C9' C16' N2' 127.7(2) . . . . ? C8' C9' C16' N2' -116.4(2) . . . . ? C16' N2' C17' C18' -146.3(2) . . . . ? C16' N2' C17' C25' 90.6(3) . . . . ? N2' C17' C18' C19' 61.1(3) . . . . ? C25' C17' C18' C19' -173.2(2) . . . . ? C17' C18' C19' C24' 99.6(3) . . . . ? C17' C18' C19' C20' -81.9(3) . . . . ? C24' C19' C20' C21' -0.4(4) . . . . ? C18' C19' C20' C21' -178.9(3) . . . . ? C19' C20' C21' C22' -0.4(5) . . . . ? C20' C21' C22' C23' 0.7(5) . . . . ? C21' C22' C23' C24' -0.3(4) . . . . ? C22' C23' C24' C19' -0.5(4) . . . . ? C20' C19' C24' C23' 0.8(4) . . . . ? C18' C19' C24' C23' 179.3(2) . . . . ? C26' N3' C25' O3' 2.3(4) . . . . ? C26' N3' C25' C17' -177.7(2) . . . . ? N2' C17' C25' O3' 169.0(2) . . . . ? C18' C17' C25' O3' 45.1(3) . . . . ? N2' C17' C25' N3' -11.0(3) . . . . ? C18' C17' C25' N3' -134.9(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3 O1 0.99 1.93 2.880(3) 158.7 . N3' H3' O1' 0.95 1.95 2.856(3) 158.4 . N2 H2 O2' 0.93 2.05 2.965(2) 168.6 . N2' H2' O2 0.91 2.03 2.934(2) 171.5 1_655 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.189 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.039 # Attachment '4a.cif' data_Boc-(S,R)-(betaPh)Pro-D-Phe-NHMe_compound_4a _database_code_depnum_ccdc_archive 'CCDC 842885' #TrackingRef '4a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '(2S,3R)-N-(tert-butoxycarbonyl)-3-phenylprolyl-(R)-N'-methylphenylalaninamide' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H33 N3 O4' _chemical_formula_sum 'C26 H33 N3 O4' _chemical_formula_weight 451.55 _chemical_absolute_configuration syn 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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 13.539(2) _cell_length_b 13.615(2) _cell_length_c 13.6874(17) _cell_angle_alpha 90.00 _cell_angle_beta 97.1390(12) _cell_angle_gamma 90.00 _cell_volume 2503.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.59 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.198 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Xcalibur, Sapphire3' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14654 _diffrn_reflns_av_R_equivalents 0.0766 _diffrn_reflns_av_sigmaI/netI 0.1553 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 25.25 _reflns_number_total 7271 _reflns_number_gt 3686 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0414P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7271 _refine_ls_number_parameters 597 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1341 _refine_ls_R_factor_gt 0.0558 _refine_ls_wR_factor_ref 0.1083 _refine_ls_wR_factor_gt 0.0906 _refine_ls_goodness_of_fit_ref 0.873 _refine_ls_restrained_S_all 0.873 _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 O0 O 0.1576(2) 0.5791(2) 0.2490(2) 0.0367(8) Uani 1 1 d . . . O1 O 0.2848(2) 0.6836(2) 0.3017(2) 0.0404(9) Uani 1 1 d . . . O2 O 0.4479(2) 0.5405(2) 0.4400(2) 0.0418(9) Uani 1 1 d . . . O3 O 0.6527(2) 0.7550(2) 0.3457(2) 0.0382(8) Uani 1 1 d . . . N1 N 0.2308(3) 0.5707(3) 0.4040(3) 0.0302(10) Uani 1 1 d . . . N2 N 0.4487(2) 0.6998(3) 0.4849(2) 0.0269(9) Uani 1 1 d . . . H2 H 0.4082 0.7622 0.4912 0.032 Uiso 1 1 d R . . N3 N 0.4863(3) 0.7561(3) 0.3030(2) 0.0354(10) Uani 1 1 d . . . H3 H 0.4143 0.7421 0.3182 0.042 Uiso 1 1 d R . . C1 C 0.2517(4) 0.5616(4) 0.1108(3) 0.0589(16) Uani 1 1 d . . . H1A H 0.2547 0.4908 0.1238 0.088 Uiso 1 1 calc R . . H1B H 0.3100 0.5935 0.1469 0.088 Uiso 1 1 calc R . . H1C H 0.2512 0.5732 0.0401 0.088 Uiso 1 1 calc R . . C2 C 0.0664(4) 0.5503(4) 0.0958(3) 0.0553(16) Uani 1 1 d . . . H2A H 0.0746 0.4795 0.1069 0.083 Uiso 1 1 calc R . . H2B H 0.0580 0.5637 0.0249 0.083 Uiso 1 1 calc R . . H2C H 0.0075 0.5732 0.1241 0.083 Uiso 1 1 calc R . . C3 C 0.1466(4) 0.7137(4) 0.1263(3) 0.0560(16) Uani 1 1 d . . . H3A H 0.0844 0.7366 0.1482 0.084 Uiso 1 1 calc R . . H3B H 0.1455 0.7272 0.0558 0.084 Uiso 1 1 calc R . . H3C H 0.2029 0.7481 0.1632 0.084 Uiso 1 1 calc R . . C4 C 0.1576(3) 0.6037(4) 0.1443(3) 0.0372(13) Uani 1 1 d . . . C5 C 0.2287(4) 0.6158(4) 0.3167(3) 0.0360(12) Uani 1 1 d . . . C6 C 0.1680(3) 0.4886(3) 0.4288(3) 0.0334(12) Uani 1 1 d . . . H6A H 0.1934 0.4250 0.4072 0.040 Uiso 1 1 calc R . . H6B H 0.0982 0.4972 0.3987 0.040 Uiso 1 1 calc R . . C7 C 0.1768(3) 0.4951(3) 0.5391(3) 0.0339(12) Uani 1 1 d . . . H7A H 0.1671 0.4299 0.5685 0.041 Uiso 1 1 calc R . . H7B H 0.1271 0.5414 0.5601 0.041 Uiso 1 1 calc R . . C8 C 0.2820(3) 0.5323(3) 0.5692(3) 0.0297(12) Uani 1 1 d . . . H8A H 0.3280 0.4763 0.5611 0.036 Uiso 1 1 calc R . . C9 C 0.2965(3) 0.6078(3) 0.4881(3) 0.0284(11) Uani 1 1 d . . . H9A H 0.2739 0.6742 0.5072 0.034 Uiso 1 1 calc R . . C10 C 0.3050(3) 0.5679(4) 0.6744(3) 0.0304(12) Uani 1 1 d . . . C11 C 0.3268(4) 0.4983(4) 0.7471(3) 0.0438(14) Uani 1 1 d . . . H11A H 0.3287 0.4308 0.7299 0.053 Uiso 1 1 calc R . . C12 C 0.3460(4) 0.5261(4) 0.8456(3) 0.0538(16) Uani 1 1 d . . . H12A H 0.3590 0.4776 0.8954 0.065 Uiso 1 1 calc R . . C13 C 0.3463(4) 0.6236(4) 0.8705(3) 0.0450(14) Uani 1 1 d . . . H13A H 0.3624 0.6432 0.9371 0.054 Uiso 1 1 calc R . . C14 C 0.3231(4) 0.6925(4) 0.7983(3) 0.0506(15) Uani 1 1 d . . . H14A H 0.3211 0.7600 0.8157 0.061 Uiso 1 1 calc R . . C15 C 0.3030(3) 0.6657(4) 0.7018(3) 0.0397(13) Uani 1 1 d . . . H15A H 0.2874 0.7147 0.6528 0.048 Uiso 1 1 calc R . . C16 C 0.4041(3) 0.6122(4) 0.4674(3) 0.0317(12) Uani 1 1 d . . . C17 C 0.5519(3) 0.7161(3) 0.4725(3) 0.0271(11) Uani 1 1 d . . . H17A H 0.5886 0.6533 0.4887 0.033 Uiso 1 1 calc R . . C18 C 0.5977(3) 0.7939(3) 0.5439(3) 0.0322(12) Uani 1 1 d . . . H18A H 0.6686 0.8020 0.5347 0.039 Uiso 1 1 calc R . . H18B H 0.5639 0.8573 0.5272 0.039 Uiso 1 1 calc R . . C19 C 0.5914(3) 0.7720(3) 0.6500(3) 0.0296(12) Uani 1 1 d . . . C20 C 0.5852(3) 0.6778(4) 0.6858(3) 0.0370(13) Uani 1 1 d . . . H20A H 0.5823 0.6242 0.6412 0.044 Uiso 1 1 calc R . . C21 C 0.5832(3) 0.6591(4) 0.7854(3) 0.0472(14) Uani 1 1 d . . . H21A H 0.5778 0.5935 0.8079 0.057 Uiso 1 1 calc R . . C22 C 0.5890(3) 0.7356(4) 0.8513(4) 0.0466(14) Uani 1 1 d . . . H22A H 0.5909 0.7228 0.9197 0.056 Uiso 1 1 calc R . . C23 C 0.5920(3) 0.8306(4) 0.8179(4) 0.0434(14) Uani 1 1 d . . . H23A H 0.5923 0.8840 0.8626 0.052 Uiso 1 1 calc R . . C24 C 0.5946(3) 0.8478(4) 0.7183(4) 0.0366(12) Uani 1 1 d . . . H24A H 0.5987 0.9137 0.6961 0.044 Uiso 1 1 calc R . . C25 C 0.5669(4) 0.7442(3) 0.3666(3) 0.0298(11) Uani 1 1 d . . . C26 C 0.4930(4) 0.7800(4) 0.2007(3) 0.0518(15) Uani 1 1 d . . . H26A H 0.5497 0.7452 0.1787 0.078 Uiso 1 1 calc R . . H26B H 0.5024 0.8509 0.1941 0.078 Uiso 1 1 calc R . . H26C H 0.4316 0.7599 0.1601 0.078 Uiso 1 1 calc R . . O0' O 0.9759(2) 0.7360(3) 0.6851(2) 0.0474(9) Uani 1 1 d . . . O1' O 0.8326(2) 0.6736(2) 0.6046(2) 0.0379(8) Uani 1 1 d . . . O2' O 0.9354(2) 0.5374(2) 0.4437(2) 0.0418(9) Uani 1 1 d . . . O3' O 0.6854(2) 0.3507(2) 0.4744(2) 0.0471(9) Uani 1 1 d . . . N1' N 0.9540(3) 0.7340(3) 0.5217(3) 0.0339(10) Uani 1 1 d . . . N2' N 0.7760(3) 0.5819(3) 0.3890(2) 0.0264(9) Uani 1 1 d . . . H2' H 0.7331 0.6445 0.3682 0.032 Uiso 1 1 d R . . N3' N 0.7287(3) 0.4897(3) 0.5578(3) 0.0326(10) Uani 1 1 d . . . H3' H 0.7557 0.5615 0.5513 0.039 Uiso 1 1 d R . . C1' C 0.9378(5) 0.6139(5) 0.8038(4) 0.098(3) Uani 1 1 d . . . H1D H 0.8821 0.5867 0.7596 0.147 Uiso 1 1 calc R . . H1E H 0.9254 0.6049 0.8723 0.147 Uiso 1 1 calc R . . H1F H 0.9994 0.5799 0.7932 0.147 Uiso 1 1 calc R . . C2' C 1.0328(4) 0.7678(4) 0.8485(3) 0.0618(17) Uani 1 1 d . . . H2D H 1.0373 0.8379 0.8331 0.093 Uiso 1 1 calc R . . H2E H 1.0950 0.7351 0.8379 0.093 Uiso 1 1 calc R . . H2F H 1.0215 0.7600 0.9174 0.093 Uiso 1 1 calc R . . C3' C 0.8529(4) 0.7783(4) 0.7935(3) 0.0641(17) Uani 1 1 d . . . H3D H 0.7975 0.7485 0.7508 0.096 Uiso 1 1 calc R . . H3E H 0.8604 0.8470 0.7745 0.096 Uiso 1 1 calc R . . H3F H 0.8394 0.7752 0.8621 0.096 Uiso 1 1 calc R . . C4' C 0.9481(4) 0.7228(4) 0.7829(3) 0.0416(13) Uani 1 1 d . . . C5' C 0.9153(4) 0.7118(4) 0.6049(3) 0.0353(12) Uani 1 1 d . . . C6' C 1.0518(3) 0.7781(3) 0.5157(3) 0.0440(14) Uani 1 1 d . . . H6D H 1.1056 0.7288 0.5284 0.053 Uiso 1 1 calc R . . H6E H 1.0650 0.8330 0.5630 0.053 Uiso 1 1 calc R . . C7' C 1.0423(3) 0.8141(4) 0.4112(3) 0.0442(14) Uani 1 1 d . . . H7D H 1.1080 0.8156 0.3866 0.053 Uiso 1 1 calc R . . H7E H 1.0130 0.8808 0.4059 0.053 Uiso 1 1 calc R . . C8' C 0.9732(3) 0.7396(3) 0.3535(3) 0.0346(12) Uani 1 1 d . . . H8D H 1.0138 0.6801 0.3426 0.042 Uiso 1 1 calc R . . C9' C 0.8994(3) 0.7106(3) 0.4269(3) 0.0301(12) Uani 1 1 d . . . H9D H 0.8376 0.7514 0.4150 0.036 Uiso 1 1 calc R . . C10' C 0.9212(3) 0.7708(4) 0.2556(3) 0.0359(13) Uani 1 1 d . . . C11' C 0.8640(4) 0.7045(4) 0.1965(4) 0.0467(14) Uani 1 1 d . . . H11D H 0.8598 0.6385 0.2182 0.056 Uiso 1 1 calc R . . C12' C 0.8130(4) 0.7312(5) 0.1075(4) 0.0606(16) Uani 1 1 d . . . H12D H 0.7745 0.6836 0.0687 0.073 Uiso 1 1 calc R . . C13' C 0.8171(5) 0.8269(5) 0.0737(4) 0.0637(17) Uani 1 1 d . . . H13D H 0.7819 0.8462 0.0123 0.076 Uiso 1 1 calc R . . C14' C 0.8733(5) 0.8921(5) 0.1315(4) 0.074(2) Uani 1 1 d . . . H14D H 0.8772 0.9579 0.1094 0.088 Uiso 1 1 calc R . . C15' C 0.9248(4) 0.8664(4) 0.2208(4) 0.0593(17) Uani 1 1 d . . . H15D H 0.9631 0.9144 0.2590 0.071 Uiso 1 1 calc R . . C16' C 0.8729(4) 0.6011(4) 0.4212(3) 0.0301(12) Uani 1 1 d . . . C17' C 0.7389(3) 0.4816(3) 0.3801(3) 0.0300(12) Uani 1 1 d . . . H17D H 0.7925 0.4405 0.3568 0.036 Uiso 1 1 calc R . . C18' C 0.6484(3) 0.4738(3) 0.3031(3) 0.0361(13) Uani 1 1 d . . . H18D H 0.5997 0.5244 0.3174 0.043 Uiso 1 1 calc R . . H18E H 0.6171 0.4089 0.3101 0.043 Uiso 1 1 calc R . . C19' C 0.6675(4) 0.4856(4) 0.1964(3) 0.0369(12) Uani 1 1 d . . . C20' C 0.7544(4) 0.4550(4) 0.1631(4) 0.0513(15) Uani 1 1 d . . . H20D H 0.8073 0.4317 0.2095 0.062 Uiso 1 1 calc R . . C21' C 0.7671(4) 0.4571(4) 0.0641(4) 0.0592(16) Uani 1 1 d . . . H21D H 0.8281 0.4367 0.0429 0.071 Uiso 1 1 calc R . . C22' C 0.6892(5) 0.4895(4) -0.0027(4) 0.0672(18) Uani 1 1 d . . . H22D H 0.6959 0.4900 -0.0710 0.081 Uiso 1 1 calc R . . C23' C 0.6018(5) 0.5210(4) 0.0289(4) 0.0690(19) Uani 1 1 d . . . H23D H 0.5485 0.5441 -0.0172 0.083 Uiso 1 1 calc R . . C24' C 0.5925(4) 0.5188(4) 0.1273(4) 0.0577(16) Uani 1 1 d . . . H24D H 0.5322 0.5410 0.1487 0.069 Uiso 1 1 calc R . . C25' C 0.7153(3) 0.4371(4) 0.4767(3) 0.0339(12) Uani 1 1 d . . . C26' C 0.7073(4) 0.4485(4) 0.6507(3) 0.0484(14) Uani 1 1 d . . . H26D H 0.7424 0.3858 0.6624 0.073 Uiso 1 1 calc R . . H26E H 0.6355 0.4376 0.6482 0.073 Uiso 1 1 calc R . . H26F H 0.7295 0.4942 0.7043 0.073 Uiso 1 1 calc 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 O0 0.034(2) 0.046(2) 0.0286(18) -0.0046(16) 0.0007(15) -0.0081(17) O1 0.041(2) 0.042(2) 0.0369(18) 0.0052(17) 0.0007(16) -0.0136(19) O2 0.033(2) 0.027(2) 0.069(2) -0.0097(18) 0.0209(17) -0.0037(16) O3 0.031(2) 0.037(2) 0.049(2) 0.0118(17) 0.0106(16) 0.0047(17) N1 0.028(2) 0.038(3) 0.025(2) 0.0018(19) 0.0036(18) -0.0057(19) N2 0.022(2) 0.020(3) 0.039(2) -0.0023(18) 0.0087(17) 0.0053(18) N3 0.027(2) 0.041(3) 0.037(2) 0.008(2) 0.002(2) 0.002(2) C1 0.058(4) 0.071(5) 0.050(3) -0.007(3) 0.018(3) 0.009(3) C2 0.058(4) 0.064(4) 0.039(3) 0.000(3) -0.012(3) 0.001(3) C3 0.068(4) 0.045(4) 0.053(3) 0.013(3) -0.001(3) 0.005(3) C4 0.037(3) 0.043(4) 0.030(3) 0.001(3) -0.002(2) 0.001(3) C5 0.031(3) 0.040(4) 0.037(3) -0.010(3) 0.005(3) 0.012(3) C6 0.024(3) 0.037(3) 0.040(3) -0.005(2) 0.005(2) -0.008(2) C7 0.032(3) 0.031(3) 0.039(3) 0.000(2) 0.005(2) 0.001(2) C8 0.033(3) 0.029(3) 0.027(3) 0.001(2) 0.006(2) 0.003(2) C9 0.024(3) 0.031(3) 0.030(3) -0.002(2) 0.003(2) 0.001(2) C10 0.026(3) 0.033(3) 0.033(3) 0.004(3) 0.007(2) -0.002(2) C11 0.063(4) 0.032(3) 0.036(3) 0.002(3) 0.006(3) 0.003(3) C12 0.075(4) 0.048(4) 0.038(3) 0.010(3) 0.005(3) -0.008(3) C13 0.051(4) 0.054(4) 0.032(3) -0.012(3) 0.010(3) -0.012(3) C14 0.067(4) 0.042(4) 0.044(3) 0.001(3) 0.012(3) 0.002(3) C15 0.050(4) 0.037(4) 0.032(3) 0.001(3) 0.007(2) 0.000(3) C16 0.039(3) 0.025(3) 0.031(3) -0.004(2) 0.005(2) -0.008(3) C17 0.021(3) 0.026(3) 0.036(3) 0.003(2) 0.009(2) 0.004(2) C18 0.027(3) 0.026(3) 0.042(3) 0.000(2) 0.001(2) 0.002(2) C19 0.031(3) 0.022(3) 0.035(3) -0.004(3) 0.001(2) -0.002(2) C20 0.031(3) 0.038(4) 0.041(3) -0.002(3) 0.003(2) 0.002(2) C21 0.052(4) 0.039(4) 0.051(4) 0.007(3) 0.006(3) -0.002(3) C22 0.051(3) 0.050(4) 0.037(3) 0.004(3) 0.001(3) -0.001(3) C23 0.036(3) 0.049(4) 0.045(3) -0.009(3) 0.006(3) 0.004(3) C24 0.029(3) 0.032(3) 0.049(3) -0.001(3) 0.004(2) -0.001(2) C25 0.033(3) 0.016(3) 0.042(3) 0.004(2) 0.009(3) 0.005(2) C26 0.057(4) 0.058(4) 0.039(3) 0.017(3) 0.003(3) 0.000(3) O0' 0.033(2) 0.070(3) 0.037(2) -0.0104(18) -0.0038(17) -0.0009(19) O1' 0.034(2) 0.037(2) 0.0423(19) -0.0059(16) 0.0061(16) -0.0077(17) O2' 0.033(2) 0.028(2) 0.064(2) 0.0090(18) 0.0020(17) 0.0056(17) O3' 0.055(2) 0.029(2) 0.061(2) 0.0001(19) 0.0242(18) -0.0093(19) N1' 0.028(2) 0.034(3) 0.039(2) -0.003(2) 0.005(2) -0.007(2) N2' 0.022(2) 0.017(2) 0.040(2) 0.0045(18) 0.0063(18) -0.0023(18) N3' 0.043(3) 0.016(2) 0.041(2) 0.005(2) 0.0143(19) -0.0017(19) C1' 0.142(7) 0.057(5) 0.082(5) 0.019(4) -0.038(4) -0.006(5) C2' 0.052(4) 0.089(5) 0.041(3) -0.013(3) -0.008(3) 0.006(3) C3' 0.060(4) 0.086(5) 0.045(3) -0.013(3) 0.002(3) 0.006(4) C4' 0.041(3) 0.042(4) 0.037(3) 0.002(3) -0.014(3) 0.004(3) C5' 0.027(3) 0.034(3) 0.043(3) 0.000(3) -0.004(3) 0.001(3) C6' 0.030(3) 0.032(3) 0.068(4) -0.008(3) 0.002(3) -0.007(3) C7' 0.028(3) 0.044(4) 0.061(3) 0.004(3) 0.007(3) -0.006(3) C8' 0.034(3) 0.020(3) 0.053(3) -0.004(3) 0.018(2) 0.002(2) C9' 0.026(3) 0.028(3) 0.037(3) -0.004(2) 0.006(2) -0.003(2) C10' 0.033(3) 0.038(4) 0.040(3) 0.001(3) 0.018(2) -0.003(3) C11' 0.055(4) 0.041(4) 0.046(3) 0.003(3) 0.015(3) -0.007(3) C12' 0.072(4) 0.064(5) 0.045(4) 0.007(3) 0.009(3) -0.012(4) C13' 0.078(5) 0.068(5) 0.046(3) 0.008(4) 0.014(3) 0.007(4) C14' 0.114(6) 0.044(4) 0.061(4) 0.017(4) 0.004(4) -0.009(4) C15' 0.088(5) 0.039(4) 0.052(4) 0.002(3) 0.013(3) -0.012(3) C16' 0.034(3) 0.032(4) 0.027(3) -0.005(2) 0.014(2) -0.004(3) C17' 0.030(3) 0.024(3) 0.037(3) 0.000(2) 0.008(2) 0.002(2) C18' 0.034(3) 0.024(3) 0.051(3) -0.005(2) 0.006(2) -0.006(2) C19' 0.032(3) 0.029(3) 0.047(3) -0.003(3) -0.002(3) -0.005(2) C20' 0.057(4) 0.047(4) 0.050(4) 0.005(3) 0.006(3) 0.011(3) C21' 0.074(5) 0.058(4) 0.046(3) 0.001(3) 0.008(3) 0.002(3) C22' 0.081(5) 0.075(5) 0.043(3) 0.007(3) -0.003(4) -0.005(4) C23' 0.061(5) 0.081(5) 0.059(4) 0.023(4) -0.017(3) -0.014(4) C24' 0.043(4) 0.053(4) 0.074(4) 0.005(3) -0.001(3) -0.006(3) C25' 0.033(3) 0.032(4) 0.037(3) 0.000(3) 0.008(2) 0.001(3) C26' 0.054(4) 0.045(4) 0.048(3) 0.011(3) 0.017(3) 0.009(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 O0 C5 1.347(5) . ? O0 C4 1.471(5) . ? O1 C5 1.229(5) . ? O2 C16 1.225(5) . ? O3 C25 1.240(5) . ? N1 C5 1.341(5) . ? N1 C9 1.454(5) . ? N1 C6 1.470(5) . ? N2 C16 1.344(5) . ? N2 C17 1.446(5) . ? N2 H2 1.0209 . ? N3 C25 1.318(5) . ? N3 C26 1.452(5) . ? N3 H3 1.0393 . ? C1 C4 1.520(6) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C4 1.513(6) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.522(6) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C6 C7 1.503(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.519(6) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C10 1.515(5) . ? C8 C9 1.543(5) . ? C8 H8A 1.0000 . ? C9 C16 1.520(6) . ? C9 H9A 1.0000 . ? C10 C11 1.380(6) . ? C10 C15 1.384(6) . ? C11 C12 1.393(6) . ? C11 H11A 0.9500 . ? C12 C13 1.370(6) . ? C12 H12A 0.9500 . ? C13 C14 1.371(6) . ? C13 H13A 0.9500 . ? C14 C15 1.365(5) . ? C14 H14A 0.9500 . ? C15 H15A 0.9500 . ? C17 C18 1.520(5) . ? C17 C25 1.537(5) . ? C17 H17A 1.0000 . ? C18 C19 1.495(5) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.380(6) . ? C19 C24 1.390(6) . ? C20 C21 1.391(6) . ? C20 H20A 0.9500 . ? C21 C22 1.373(6) . ? C21 H21A 0.9500 . ? C22 C23 1.374(6) . ? C22 H22A 0.9500 . ? C23 C24 1.389(6) . ? C23 H23A 0.9500 . ? C24 H24A 0.9500 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? O0' C5' 1.328(5) . ? O0' C4' 1.446(5) . ? O1' C5' 1.233(5) . ? O2' C16' 1.223(5) . ? O3' C25' 1.243(5) . ? N1' C5' 1.346(5) . ? N1' C9' 1.447(5) . ? N1' C6' 1.466(5) . ? N2' C16' 1.357(5) . ? N2' C17' 1.455(5) . ? N2' H2' 1.0505 . ? N3' C25' 1.314(5) . ? N3' C26' 1.452(5) . ? N3' H3' 1.0519 . ? C1' C4' 1.520(7) . ? C1' H1D 0.9800 . ? C1' H1E 0.9800 . ? C1' H1F 0.9800 . ? C2' C4' 1.497(6) . ? C2' H2D 0.9800 . ? C2' H2E 0.9800 . ? C2' H2F 0.9800 . ? C3' C4' 1.517(6) . ? C3' H3D 0.9800 . ? C3' H3E 0.9800 . ? C3' H3F 0.9800 . ? C6' C7' 1.502(6) . ? C6' H6D 0.9900 . ? C6' H6E 0.9900 . ? C7' C8' 1.531(6) . ? C7' H7D 0.9900 . ? C7' H7E 0.9900 . ? C8' C10' 1.496(6) . ? C8' C9' 1.553(6) . ? C8' H8D 1.0000 . ? C9' C16' 1.534(6) . ? C9' H9D 1.0000 . ? C10' C11' 1.383(6) . ? C10' C15' 1.390(6) . ? C11' C12' 1.373(6) . ? C11' H11D 0.9500 . ? C12' C13' 1.386(7) . ? C12' H12D 0.9500 . ? C13' C14' 1.357(7) . ? C13' H13D 0.9500 . ? C14' C15' 1.375(7) . ? C14' H14D 0.9500 . ? C15' H15D 0.9500 . ? C17' C18' 1.517(5) . ? C17' C25' 1.524(6) . ? C17' H17D 1.0000 . ? C18' C19' 1.523(6) . ? C18' H18D 0.9900 . ? C18' H18E 0.9900 . ? C19' C24' 1.375(6) . ? C19' C20' 1.378(6) . ? C20' C21' 1.387(6) . ? C20' H20D 0.9500 . ? C21' C22' 1.380(7) . ? C21' H21D 0.9500 . ? C22' C23' 1.378(7) . ? C22' H22D 0.9500 . ? C23' C24' 1.369(7) . ? C23' H23D 0.9500 . ? C24' H24D 0.9500 . ? C26' H26D 0.9800 . ? C26' H26E 0.9800 . ? C26' H26F 0.9800 . ? 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 C5 O0 C4 120.0(4) . . ? C5 N1 C9 119.3(4) . . ? C5 N1 C6 127.2(4) . . ? C9 N1 C6 113.4(3) . . ? C16 N2 C17 122.3(4) . . ? C16 N2 H2 121.3 . . ? C17 N2 H2 114.8 . . ? C25 N3 C26 121.3(4) . . ? C25 N3 H3 124.4 . . ? C26 N3 H3 114.0 . . ? C4 C1 H1A 109.5 . . ? C4 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C4 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C4 C2 H2A 109.5 . . ? C4 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C4 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C4 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? O0 C4 C2 102.7(4) . . ? O0 C4 C1 108.0(4) . . ? C2 C4 C1 110.8(4) . . ? O0 C4 C3 111.7(4) . . ? C2 C4 C3 110.1(4) . . ? C1 C4 C3 113.0(4) . . ? O1 C5 N1 123.2(4) . . ? O1 C5 O0 124.5(4) . . ? N1 C5 O0 112.2(5) . . ? N1 C6 C7 102.1(3) . . ? N1 C6 H6A 111.3 . . ? C7 C6 H6A 111.3 . . ? N1 C6 H6B 111.3 . . ? C7 C6 H6B 111.3 . . ? H6A C6 H6B 109.2 . . ? C6 C7 C8 104.3(3) . . ? C6 C7 H7A 110.9 . . ? C8 C7 H7A 110.9 . . ? C6 C7 H7B 110.9 . . ? C8 C7 H7B 110.9 . . ? H7A C7 H7B 108.9 . . ? C10 C8 C7 116.1(3) . . ? C10 C8 C9 116.2(4) . . ? C7 C8 C9 103.0(3) . . ? C10 C8 H8A 107.0 . . ? C7 C8 H8A 107.0 . . ? C9 C8 H8A 107.0 . . ? N1 C9 C16 111.9(3) . . ? N1 C9 C8 102.6(3) . . ? C16 C9 C8 111.8(3) . . ? N1 C9 H9A 110.1 . . ? C16 C9 H9A 110.1 . . ? C8 C9 H9A 110.1 . . ? C11 C10 C15 118.4(4) . . ? C11 C10 C8 117.8(4) . . ? C15 C10 C8 123.8(4) . . ? C10 C11 C12 120.6(5) . . ? C10 C11 H11A 119.7 . . ? C12 C11 H11A 119.7 . . ? C13 C12 C11 119.9(5) . . ? C13 C12 H12A 120.1 . . ? C11 C12 H12A 120.1 . . ? C12 C13 C14 119.4(5) . . ? C12 C13 H13A 120.3 . . ? C14 C13 H13A 120.3 . . ? C15 C14 C13 121.0(5) . . ? C15 C14 H14A 119.5 . . ? C13 C14 H14A 119.5 . . ? C14 C15 C10 120.7(5) . . ? C14 C15 H15A 119.6 . . ? C10 C15 H15A 119.6 . . ? O2 C16 N2 122.5(4) . . ? O2 C16 C9 122.5(4) . . ? N2 C16 C9 114.9(4) . . ? N2 C17 C18 110.7(3) . . ? N2 C17 C25 113.1(3) . . ? C18 C17 C25 110.0(4) . . ? N2 C17 H17A 107.6 . . ? C18 C17 H17A 107.6 . . ? C25 C17 H17A 107.6 . . ? C19 C18 C17 114.7(4) . . ? C19 C18 H18A 108.6 . . ? C17 C18 H18A 108.6 . . ? C19 C18 H18B 108.6 . . ? C17 C18 H18B 108.6 . . ? H18A C18 H18B 107.6 . . ? C20 C19 C24 116.7(4) . . ? C20 C19 C18 123.0(4) . . ? C24 C19 C18 120.3(4) . . ? C19 C20 C21 121.9(5) . . ? C19 C20 H20A 119.0 . . ? C21 C20 H20A 119.0 . . ? C22 C21 C20 119.9(5) . . ? C22 C21 H21A 120.1 . . ? C20 C21 H21A 120.1 . . ? C21 C22 C23 119.8(5) . . ? C21 C22 H22A 120.1 . . ? C23 C22 H22A 120.1 . . ? C22 C23 C24 119.4(5) . . ? C22 C23 H23A 120.3 . . ? C24 C23 H23A 120.3 . . ? C23 C24 C19 122.2(5) . . ? C23 C24 H24A 118.9 . . ? C19 C24 H24A 118.9 . . ? O3 C25 N3 123.7(4) . . ? O3 C25 C17 119.0(4) . . ? N3 C25 C17 117.3(4) . . ? N3 C26 H26A 109.5 . . ? N3 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N3 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C5' O0' C4' 122.0(4) . . ? C5' N1' C9' 120.0(4) . . ? C5' N1' C6' 126.1(4) . . ? C9' N1' C6' 113.9(4) . . ? C16' N2' C17' 121.2(4) . . ? C16' N2' H2' 114.3 . . ? C17' N2' H2' 124.5 . . ? C25' N3' C26' 120.5(4) . . ? C25' N3' H3' 116.6 . . ? C26' N3' H3' 122.9 . . ? C4' C1' H1D 109.5 . . ? C4' C1' H1E 109.5 . . ? H1D C1' H1E 109.5 . . ? C4' C1' H1F 109.5 . . ? H1D C1' H1F 109.5 . . ? H1E C1' H1F 109.5 . . ? C4' C2' H2D 109.5 . . ? C4' C2' H2E 109.5 . . ? H2D C2' H2E 109.5 . . ? C4' C2' H2F 109.5 . . ? H2D C2' H2F 109.5 . . ? H2E C2' H2F 109.5 . . ? C4' C3' H3D 109.5 . . ? C4' C3' H3E 109.5 . . ? H3D C3' H3E 109.5 . . ? C4' C3' H3F 109.5 . . ? H3D C3' H3F 109.5 . . ? H3E C3' H3F 109.5 . . ? O0' C4' C2' 103.7(4) . . ? O0' C4' C3' 110.4(4) . . ? C2' C4' C3' 109.6(4) . . ? O0' C4' C1' 109.7(4) . . ? C2' C4' C1' 111.6(4) . . ? C3' C4' C1' 111.6(5) . . ? O1' C5' O0' 125.0(4) . . ? O1' C5' N1' 122.8(4) . . ? O0' C5' N1' 112.2(4) . . ? N1' C6' C7' 102.4(4) . . ? N1' C6' H6D 111.3 . . ? C7' C6' H6D 111.3 . . ? N1' C6' H6E 111.3 . . ? C7' C6' H6E 111.3 . . ? H6D C6' H6E 109.2 . . ? C6' C7' C8' 104.5(4) . . ? C6' C7' H7D 110.9 . . ? C8' C7' H7D 110.9 . . ? C6' C7' H7E 110.9 . . ? C8' C7' H7E 110.9 . . ? H7D C7' H7E 108.9 . . ? C10' C8' C7' 117.6(4) . . ? C10' C8' C9' 112.5(4) . . ? C7' C8' C9' 103.6(3) . . ? C10' C8' H8D 107.6 . . ? C7' C8' H8D 107.6 . . ? C9' C8' H8D 107.6 . . ? N1' C9' C16' 110.4(3) . . ? N1' C9' C8' 103.0(3) . . ? C16' C9' C8' 112.3(3) . . ? N1' C9' H9D 110.3 . . ? C16' C9' H9D 110.3 . . ? C8' C9' H9D 110.3 . . ? C11' C10' C15' 116.8(5) . . ? C11' C10' C8' 120.4(5) . . ? C15' C10' C8' 122.7(5) . . ? C12' C11' C10' 122.0(5) . . ? C12' C11' H11D 119.0 . . ? C10' C11' H11D 119.0 . . ? C11' C12' C13' 120.5(5) . . ? C11' C12' H12D 119.7 . . ? C13' C12' H12D 119.7 . . ? C14' C13' C12' 117.6(5) . . ? C14' C13' H13D 121.2 . . ? C12' C13' H13D 121.2 . . ? C13' C14' C15' 122.5(6) . . ? C13' C14' H14D 118.7 . . ? C15' C14' H14D 118.7 . . ? C14' C15' C10' 120.5(5) . . ? C14' C15' H15D 119.7 . . ? C10' C15' H15D 119.7 . . ? O2' C16' N2' 123.7(4) . . ? O2' C16' C9' 121.8(4) . . ? N2' C16' C9' 114.5(4) . . ? N2' C17' C18' 111.4(4) . . ? N2' C17' C25' 114.1(4) . . ? C18' C17' C25' 109.7(4) . . ? N2' C17' H17D 107.1 . . ? C18' C17' H17D 107.1 . . ? C25' C17' H17D 107.1 . . ? C17' C18' C19' 116.1(4) . . ? C17' C18' H18D 108.2 . . ? C19' C18' H18D 108.2 . . ? C17' C18' H18E 108.2 . . ? C19' C18' H18E 108.2 . . ? H18D C18' H18E 107.4 . . ? C24' C19' C20' 117.4(5) . . ? C24' C19' C18' 119.6(5) . . ? C20' C19' C18' 122.6(4) . . ? C19' C20' C21' 122.1(5) . . ? C19' C20' H20D 119.0 . . ? C21' C20' H20D 119.0 . . ? C22' C21' C20' 118.5(6) . . ? C22' C21' H21D 120.8 . . ? C20' C21' H21D 120.8 . . ? C23' C22' C21' 120.5(5) . . ? C23' C22' H22D 119.8 . . ? C21' C22' H22D 119.8 . . ? C24' C23' C22' 119.3(5) . . ? C24' C23' H23D 120.4 . . ? C22' C23' H23D 120.4 . . ? C23' C24' C19' 122.2(6) . . ? C23' C24' H24D 118.9 . . ? C19' C24' H24D 118.9 . . ? O3' C25' N3' 123.2(4) . . ? O3' C25' C17' 117.2(4) . . ? N3' C25' C17' 119.6(4) . . ? N3' C26' H26D 109.5 . . ? N3' C26' H26E 109.5 . . ? H26D C26' H26E 109.5 . . ? N3' C26' H26F 109.5 . . ? H26D C26' H26F 109.5 . . ? H26E C26' H26F 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 C5 O0 C4 C2 -178.9(4) . . . . ? C5 O0 C4 C1 64.0(5) . . . . ? C5 O0 C4 C3 -61.0(5) . . . . ? C9 N1 C5 O1 5.1(7) . . . . ? C6 N1 C5 O1 -179.2(4) . . . . ? C9 N1 C5 O0 -173.9(3) . . . . ? C6 N1 C5 O0 1.8(6) . . . . ? C4 O0 C5 O1 14.2(7) . . . . ? C4 O0 C5 N1 -166.8(4) . . . . ? C5 N1 C6 C7 -160.0(4) . . . . ? C9 N1 C6 C7 15.8(5) . . . . ? N1 C6 C7 C8 -33.1(4) . . . . ? C6 C7 C8 C10 166.7(4) . . . . ? C6 C7 C8 C9 38.5(5) . . . . ? C5 N1 C9 C16 -56.0(5) . . . . ? C6 N1 C9 C16 127.7(4) . . . . ? C5 N1 C9 C8 -176.0(4) . . . . ? C6 N1 C9 C8 7.8(5) . . . . ? C10 C8 C9 N1 -156.1(4) . . . . ? C7 C8 C9 N1 -28.0(4) . . . . ? C10 C8 C9 C16 83.9(5) . . . . ? C7 C8 C9 C16 -148.0(4) . . . . ? C7 C8 C10 C11 80.6(5) . . . . ? C9 C8 C10 C11 -158.0(4) . . . . ? C7 C8 C10 C15 -97.7(5) . . . . ? C9 C8 C10 C15 23.7(6) . . . . ? C15 C10 C11 C12 0.1(7) . . . . ? C8 C10 C11 C12 -178.3(4) . . . . ? C10 C11 C12 C13 -1.9(8) . . . . ? C11 C12 C13 C14 2.9(8) . . . . ? C12 C13 C14 C15 -2.1(8) . . . . ? C13 C14 C15 C10 0.3(7) . . . . ? C11 C10 C15 C14 0.7(7) . . . . ? C8 C10 C15 C14 179.0(4) . . . . ? C17 N2 C16 O2 0.2(6) . . . . ? C17 N2 C16 C9 177.8(3) . . . . ? N1 C9 C16 O2 -55.1(6) . . . . ? C8 C9 C16 O2 59.3(5) . . . . ? N1 C9 C16 N2 127.2(4) . . . . ? C8 C9 C16 N2 -118.4(4) . . . . ? C16 N2 C17 C18 -149.6(4) . . . . ? C16 N2 C17 C25 86.4(5) . . . . ? N2 C17 C18 C19 56.8(5) . . . . ? C25 C17 C18 C19 -177.5(4) . . . . ? C17 C18 C19 C20 26.1(6) . . . . ? C17 C18 C19 C24 -155.8(4) . . . . ? C24 C19 C20 C21 -0.6(7) . . . . ? C18 C19 C20 C21 177.6(4) . . . . ? C19 C20 C21 C22 -1.0(7) . . . . ? C20 C21 C22 C23 3.1(7) . . . . ? C21 C22 C23 C24 -3.5(7) . . . . ? C22 C23 C24 C19 1.9(7) . . . . ? C20 C19 C24 C23 0.2(7) . . . . ? C18 C19 C24 C23 -178.0(4) . . . . ? C26 N3 C25 O3 2.3(7) . . . . ? C26 N3 C25 C17 -178.3(4) . . . . ? N2 C17 C25 O3 -176.2(4) . . . . ? C18 C17 C25 O3 59.4(5) . . . . ? N2 C17 C25 N3 4.3(6) . . . . ? C18 C17 C25 N3 -120.1(4) . . . . ? C5' O0' C4' C2' -174.9(4) . . . . ? C5' O0' C4' C3' -57.6(6) . . . . ? C5' O0' C4' C1' 65.9(6) . . . . ? C4' O0' C5' O1' -2.4(7) . . . . ? C4' O0' C5' N1' 177.3(4) . . . . ? C9' N1' C5' O1' -1.8(7) . . . . ? C6' N1' C5' O1' -179.2(5) . . . . ? C9' N1' C5' O0' 178.5(4) . . . . ? C6' N1' C5' O0' 1.1(6) . . . . ? C5' N1' C6' C7' -163.3(4) . . . . ? C9' N1' C6' C7' 19.2(5) . . . . ? N1' C6' C7' C8' -32.8(5) . . . . ? C6' C7' C8' C10' 159.8(4) . . . . ? C6' C7' C8' C9' 35.0(5) . . . . ? C5' N1' C9' C16' -55.1(5) . . . . ? C6' N1' C9' C16' 122.5(4) . . . . ? C5' N1' C9' C8' -175.2(4) . . . . ? C6' N1' C9' C8' 2.4(5) . . . . ? C10' C8' C9' N1' -150.8(4) . . . . ? C7' C8' C9' N1' -22.8(4) . . . . ? C10' C8' C9' C16' 90.3(5) . . . . ? C7' C8' C9' C16' -141.6(4) . . . . ? C7' C8' C10' C11' 175.0(4) . . . . ? C9' C8' C10' C11' -64.7(5) . . . . ? C7' C8' C10' C15' -7.1(6) . . . . ? C9' C8' C10' C15' 113.1(5) . . . . ? C15' C10' C11' C12' 0.2(7) . . . . ? C8' C10' C11' C12' 178.2(4) . . . . ? C10' C11' C12' C13' -0.2(8) . . . . ? C11' C12' C13' C14' 0.2(9) . . . . ? C12' C13' C14' C15' -0.2(9) . . . . ? C13' C14' C15' C10' 0.2(9) . . . . ? C11' C10' C15' C14' -0.1(8) . . . . ? C8' C10' C15' C14' -178.1(5) . . . . ? C17' N2' C16' O2' 0.9(6) . . . . ? C17' N2' C16' C9' -179.6(3) . . . . ? N1' C9' C16' O2' -49.9(5) . . . . ? C8' C9' C16' O2' 64.5(5) . . . . ? N1' C9' C16' N2' 130.6(4) . . . . ? C8' C9' C16' N2' -115.0(4) . . . . ? C16' N2' C17' C18' -153.9(4) . . . . ? C16' N2' C17' C25' 81.2(5) . . . . ? N2' C17' C18' C19' 70.6(5) . . . . ? C25' C17' C18' C19' -162.1(4) . . . . ? C17' C18' C19' C24' -153.8(4) . . . . ? C17' C18' C19' C20' 32.9(7) . . . . ? C24' C19' C20' C21' 0.0(8) . . . . ? C18' C19' C20' C21' 173.5(5) . . . . ? C19' C20' C21' C22' -1.1(8) . . . . ? C20' C21' C22' C23' 1.5(9) . . . . ? C21' C22' C23' C24' -0.8(9) . . . . ? C22' C23' C24' C19' -0.3(9) . . . . ? C20' C19' C24' C23' 0.7(8) . . . . ? C18' C19' C24' C23' -172.9(5) . . . . ? C26' N3' C25' O3' -0.9(7) . . . . ? C26' N3' C25' C17' -179.6(4) . . . . ? N2' C17' C25' O3' -178.4(4) . . . . ? C18' C17' C25' O3' 55.8(5) . . . . ? N2' C17' C25' N3' 0.4(6) . . . . ? C18' C17' C25' N3' -125.4(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3 O1 1.04 1.91 2.900(5) 157.2 . N3' H3' O1' 1.05 1.94 2.905(5) 151.2 . N2' H2' O3 1.05 1.86 2.906(4) 173.5 . N2 H2 O3' 1.02 1.85 2.842(5) 162.8 2_656 _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.158 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.040