# Electronic Supplementary Material (ESI) for Organic and Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Hosahudya Gopi' _publ_contact_author_email hn.gopi@iiserpune.ac.in _publ_section_title ; Synthesis of alpha, beta-unsaturated gamma-amino esters with unprecedented (E)-stereoselectivity and their conformational analysis in peptides ; loop_ _publ_author_name H.Gopi S.Mali A.Bandyopadhyay S.Jadhav 'M.Ganesh Kumar' # Attachment 'Boc-dgLeu.cif' data_anudgleu _database_code_depnum_ccdc_archive 'CCDC 802255' #TrackingRef 'Boc-dgLeu.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic '(S,E)-ethyl 4-(tert-butoxycarbonylamino)-6-methylhept-2-enoate' _chemical_name_common '(S,E)-ethyl 4-(tert-butoxycarbonylamino)-6-methylhept-2-enoate' _chemical_formula_moiety 'C30 H54 N2 O8' _chemical_formula_sum 'C30 H54 N2 O8' _chemical_compound_source Synthesis _exptl_crystal_recrystallization_method Methanol _chemical_melting_point ? _exptl_crystal_description 'Retangular block' _exptl_crystal_colour Colorless _diffrn_ambient_temperature 296(2) _diffrn_ambient_pressure 101.325 _chemical_formula_weight 570.75 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 monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_int_tables_number 4 _chemical_absolute_configuration syn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.340(3) _cell_length_b 9.733(3) _cell_length_c 18.073(5) _cell_angle_alpha 90.00 _cell_angle_beta 106.331(5) _cell_angle_gamma 90.00 _cell_volume 1745.5(8) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.086 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.969 _exptl_absorpt_correction_T_max 0.982 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Graphite Monochromator' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6755 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0372 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.17 _diffrn_reflns_theta_max 24.28 _reflns_number_total 2788 _reflns_number_gt 2413 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0504P)^2^+0.1961P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.7(13) _refine_ls_number_reflns 2788 _refine_ls_number_parameters 373 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0431 _refine_ls_R_factor_gt 0.0341 _refine_ls_wR_factor_ref 0.0896 _refine_ls_wR_factor_gt 0.0804 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.985 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 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 0.7778(2) 0.7444(2) 0.04948(13) 0.0539(7) Uani 1 1 d . . . O2 O 0.6406(3) 0.9322(3) 0.02612(15) 0.0640(8) Uani 1 1 d . . . O3 O 0.8851(2) 1.2986(3) -0.14578(13) 0.0583(7) Uani 1 1 d . . . O4 O 0.8935(3) 1.0896(3) -0.19697(15) 0.0681(8) Uani 1 1 d . . . O5 O 0.7330(2) 0.0041(2) 0.46498(12) 0.0502(7) Uani 1 1 d . . . O6 O 0.8562(3) 0.1951(3) 0.51297(15) 0.0622(8) Uani 1 1 d . . . O7 O 0.5688(2) 0.5365(3) 0.65936(13) 0.0549(7) Uani 1 1 d . . . O8 O 0.5622(2) 0.3225(3) 0.70562(13) 0.0570(7) Uani 1 1 d . . . N1 N 0.8674(3) 0.9524(3) 0.06586(16) 0.0480(8) Uani 1 1 d . . . H1 H 0.9425 0.9082 0.0785 0.058 Uiso 1 1 calc R . . N2 N 0.6337(3) 0.2078(3) 0.44880(15) 0.0434(7) Uani 1 1 d . . . H2 H 0.5615 0.1616 0.4286 0.052 Uiso 1 1 calc R . . C1 C 0.6663(4) 0.6451(4) 0.0267(2) 0.0522(10) Uani 1 1 d . . . C2 C 0.7399(5) 0.5081(4) 0.0387(3) 0.0932(16) Uani 1 1 d . . . H2A H 0.8036 0.5059 0.0089 0.140 Uiso 1 1 calc R . . H2B H 0.6760 0.4349 0.0224 0.140 Uiso 1 1 calc R . . H2C H 0.7867 0.4969 0.0923 0.140 Uiso 1 1 calc R . . C3 C 0.5756(4) 0.6571(4) 0.0788(2) 0.0661(12) Uani 1 1 d . . . H3A H 0.6289 0.6525 0.1316 0.099 Uiso 1 1 calc R . . H3B H 0.5116 0.5831 0.0683 0.099 Uiso 1 1 calc R . . H3C H 0.5285 0.7432 0.0696 0.099 Uiso 1 1 calc R . . C4 C 0.5890(4) 0.6645(5) -0.0569(2) 0.0781(14) Uani 1 1 d . . . H4A H 0.5438 0.7517 -0.0633 0.117 Uiso 1 1 calc R . . H4B H 0.5238 0.5923 -0.0726 0.117 Uiso 1 1 calc R . . H4C H 0.6503 0.6619 -0.0881 0.117 Uiso 1 1 calc R . . C5 C 0.7504(4) 0.8807(4) 0.0451(2) 0.0463(10) Uani 1 1 d . . . C6 C 0.8698(4) 1.1014(3) 0.0674(2) 0.0460(10) Uani 1 1 d . . . H6 H 0.7866 1.1331 0.0777 0.055 Uiso 1 1 calc R . . C7 C 0.9890(4) 1.1503(4) 0.13381(19) 0.0527(10) Uani 1 1 d . . . H7A H 1.0705 1.1065 0.1290 0.063 Uiso 1 1 calc R . . H7B H 0.9996 1.2486 0.1288 0.063 Uiso 1 1 calc R . . C8 C 0.9748(4) 1.1206(4) 0.2138(2) 0.0588(11) Uani 1 1 d . . . H8 H 0.9473 1.0245 0.2152 0.071 Uiso 1 1 calc R . . C9 C 0.8685(5) 1.2109(5) 0.2330(2) 0.0828(14) Uani 1 1 d . . . H9A H 0.8917 1.3058 0.2298 0.124 Uiso 1 1 calc R . . H9B H 0.8645 1.1909 0.2843 0.124 Uiso 1 1 calc R . . H9C H 0.7824 1.1930 0.1970 0.124 Uiso 1 1 calc R . . C10 C 1.1094(5) 1.1398(7) 0.2744(2) 0.1075(19) Uani 1 1 d . . . H10A H 1.1739 1.0763 0.2648 0.161 Uiso 1 1 calc R . . H10B H 1.0985 1.1230 0.3246 0.161 Uiso 1 1 calc R . . H10C H 1.1406 1.2321 0.2719 0.161 Uiso 1 1 calc R . . C11 C 0.8757(3) 1.1624(4) -0.00748(19) 0.0489(10) Uani 1 1 d . . . H11 H 0.8765 1.2578 -0.0095 0.059 Uiso 1 1 calc R . . C12 C 0.8799(3) 1.0980(4) -0.0712(2) 0.0495(10) Uani 1 1 d . . . H12 H 0.8785 1.0025 -0.0724 0.059 Uiso 1 1 calc R . . C13 C 0.8866(4) 1.1738(5) -0.1399(2) 0.0511(10) Uani 1 1 d . . . C14 C 0.8997(5) 1.1536(5) -0.2696(2) 0.0763(13) Uani 1 1 d . . . H14A H 0.8504 1.2396 -0.2773 0.092 Uiso 1 1 calc R . . H14B H 0.8586 1.0933 -0.3126 0.092 Uiso 1 1 calc R . . C15 C 1.0421(4) 1.1791(5) -0.2667(2) 0.0802(14) Uani 1 1 d . . . H15A H 1.0810 1.2423 -0.2257 0.120 Uiso 1 1 calc R . . H15B H 1.0465 1.2175 -0.3148 0.120 Uiso 1 1 calc R . . H15C H 1.0911 1.0941 -0.2576 0.120 Uiso 1 1 calc R . . C16 C 0.8506(3) -0.0881(4) 0.47744(18) 0.0440(9) Uani 1 1 d . . . C17 C 0.9292(4) -0.0920(4) 0.56240(19) 0.0600(11) Uani 1 1 d . . . H17A H 0.9734 -0.0054 0.5770 0.090 Uiso 1 1 calc R . . H17B H 0.9954 -0.1639 0.5709 0.090 Uiso 1 1 calc R . . H17C H 0.8684 -0.1092 0.5929 0.090 Uiso 1 1 calc R . . C18 C 0.7855(4) -0.2269(4) 0.4519(2) 0.0620(11) Uani 1 1 d . . . H18A H 0.7299 -0.2522 0.4843 0.093 Uiso 1 1 calc R . . H18B H 0.8543 -0.2950 0.4560 0.093 Uiso 1 1 calc R . . H18C H 0.7310 -0.2210 0.3993 0.093 Uiso 1 1 calc R . . C19 C 0.9369(4) -0.0431(4) 0.42729(18) 0.0553(11) Uani 1 1 d . . . H19A H 0.8827 -0.0374 0.3747 0.083 Uiso 1 1 calc R . . H19B H 1.0080 -0.1085 0.4312 0.083 Uiso 1 1 calc R . . H19C H 0.9751 0.0454 0.4440 0.083 Uiso 1 1 calc R . . C20 C 0.7506(4) 0.1405(4) 0.4785(2) 0.0456(9) Uani 1 1 d . . . C21 C 0.6269(4) 0.3572(3) 0.45010(19) 0.0428(9) Uani 1 1 d . . . H21 H 0.7123 0.3928 0.4445 0.051 Uiso 1 1 calc R . . C22 C 0.5139(4) 0.4074(4) 0.38061(18) 0.0474(9) Uani 1 1 d . . . H22A H 0.4309 0.3619 0.3816 0.057 Uiso 1 1 calc R . . H22B H 0.5015 0.5051 0.3867 0.057 Uiso 1 1 calc R . . C23 C 0.5358(4) 0.3837(4) 0.3018(2) 0.0546(10) Uani 1 1 d . . . H23 H 0.5539 0.2859 0.2968 0.066 Uiso 1 1 calc R . . C24 C 0.6547(4) 0.4654(5) 0.2920(2) 0.0764(13) Uani 1 1 d . . . H24A H 0.6400 0.5615 0.2986 0.115 Uiso 1 1 calc R . . H24B H 0.6641 0.4500 0.2413 0.115 Uiso 1 1 calc R . . H24C H 0.7354 0.4365 0.3298 0.115 Uiso 1 1 calc R . . C25 C 0.4097(5) 0.4230(6) 0.2379(2) 0.0863(15) Uani 1 1 d . . . H25A H 0.3341 0.3714 0.2439 0.129 Uiso 1 1 calc R . . H25B H 0.4233 0.4028 0.1887 0.129 Uiso 1 1 calc R . . H25C H 0.3924 0.5194 0.2411 0.129 Uiso 1 1 calc R . . C26 C 0.6092(3) 0.4131(4) 0.52406(19) 0.0466(9) Uani 1 1 d . . . H26 H 0.6100 0.5083 0.5286 0.056 Uiso 1 1 calc R . . C27 C 0.5925(3) 0.3432(4) 0.58356(19) 0.0448(9) Uani 1 1 d . . . H27 H 0.5929 0.2476 0.5822 0.054 Uiso 1 1 calc R . . C28 C 0.5735(3) 0.4137(5) 0.6518(2) 0.0464(9) Uani 1 1 d . . . C29 C 0.5445(4) 0.3812(5) 0.7764(2) 0.0652(12) Uani 1 1 d . . . H29A H 0.6005 0.4624 0.7902 0.078 Uiso 1 1 calc R . . H29B H 0.5734 0.3151 0.8179 0.078 Uiso 1 1 calc R . . C30 C 0.4000(4) 0.4192(5) 0.7669(2) 0.0656(11) Uani 1 1 d . . . H30A H 0.3744 0.4924 0.7300 0.098 Uiso 1 1 calc R . . H30B H 0.3897 0.4489 0.8156 0.098 Uiso 1 1 calc R . . H30C H 0.3436 0.3408 0.7490 0.098 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 0.0466(16) 0.0302(17) 0.0823(18) -0.0009(12) 0.0139(13) -0.0024(13) O2 0.0419(17) 0.0445(18) 0.099(2) 0.0046(15) 0.0098(14) 0.0091(15) O3 0.0591(17) 0.0479(19) 0.0641(17) -0.0001(14) 0.0111(13) -0.0012(15) O4 0.082(2) 0.0630(18) 0.0671(18) -0.0206(16) 0.0339(15) -0.0182(16) O5 0.0444(16) 0.0292(17) 0.0741(17) -0.0051(12) 0.0122(13) 0.0031(13) O6 0.0453(17) 0.0381(17) 0.096(2) -0.0156(15) 0.0081(15) -0.0055(15) O7 0.0604(17) 0.0414(19) 0.0595(16) -0.0077(13) 0.0113(13) 0.0009(14) O8 0.0695(18) 0.0516(18) 0.0537(15) 0.0083(14) 0.0236(13) 0.0107(14) N1 0.0411(19) 0.028(2) 0.074(2) -0.0002(15) 0.0149(16) 0.0023(16) N2 0.0389(18) 0.0247(18) 0.067(2) -0.0007(15) 0.0161(15) 0.0028(16) C1 0.057(3) 0.038(2) 0.063(3) -0.004(2) 0.017(2) -0.013(2) C2 0.090(4) 0.036(3) 0.154(5) -0.009(3) 0.036(3) -0.012(3) C3 0.074(3) 0.060(3) 0.066(3) -0.005(2) 0.022(2) -0.024(2) C4 0.095(3) 0.078(3) 0.065(3) -0.014(3) 0.029(2) -0.032(3) C5 0.055(3) 0.027(3) 0.058(3) 0.0026(18) 0.017(2) 0.004(2) C6 0.052(2) 0.027(2) 0.061(2) -0.0032(19) 0.019(2) -0.0002(18) C7 0.055(2) 0.038(2) 0.067(3) -0.006(2) 0.021(2) -0.004(2) C8 0.061(3) 0.047(2) 0.069(3) 0.004(2) 0.018(2) 0.001(2) C9 0.090(3) 0.087(4) 0.082(3) -0.002(3) 0.042(3) 0.009(3) C10 0.070(3) 0.172(6) 0.074(3) -0.007(3) 0.009(3) 0.002(4) C11 0.054(2) 0.026(2) 0.069(3) 0.000(2) 0.021(2) 0.0004(18) C12 0.052(2) 0.032(2) 0.066(3) -0.008(2) 0.019(2) -0.0093(19) C13 0.042(2) 0.049(3) 0.061(3) -0.011(2) 0.014(2) -0.010(2) C14 0.082(3) 0.090(4) 0.061(3) -0.011(3) 0.027(2) -0.004(3) C15 0.082(3) 0.085(4) 0.081(3) 0.012(3) 0.037(2) 0.003(3) C16 0.047(2) 0.031(2) 0.051(2) -0.0001(18) 0.0076(18) 0.009(2) C17 0.069(3) 0.053(3) 0.055(2) 0.000(2) 0.012(2) 0.011(2) C18 0.067(3) 0.035(3) 0.079(3) -0.001(2) 0.011(2) 0.009(2) C19 0.058(2) 0.048(3) 0.058(2) 0.002(2) 0.013(2) 0.011(2) C20 0.056(3) 0.022(2) 0.062(2) -0.0062(19) 0.023(2) -0.002(2) C21 0.049(2) 0.027(2) 0.057(2) 0.0021(17) 0.023(2) 0.0019(17) C22 0.050(2) 0.036(2) 0.061(2) 0.0077(19) 0.022(2) 0.0098(19) C23 0.066(3) 0.039(2) 0.065(3) 0.0040(19) 0.027(2) 0.003(2) C24 0.080(3) 0.085(4) 0.072(3) 0.015(2) 0.035(2) 0.005(3) C25 0.079(3) 0.107(4) 0.068(3) 0.012(3) 0.014(2) -0.001(3) C26 0.048(2) 0.029(2) 0.064(2) -0.002(2) 0.019(2) 0.0074(19) C27 0.045(2) 0.027(2) 0.061(2) 0.0009(19) 0.0130(19) 0.0048(18) C28 0.038(2) 0.041(3) 0.058(3) -0.005(2) 0.0118(19) 0.003(2) C29 0.070(3) 0.078(3) 0.049(2) -0.002(2) 0.020(2) 0.013(2) C30 0.064(3) 0.081(3) 0.056(2) -0.007(2) 0.023(2) 0.002(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 O1 C5 1.354(4) . ? O1 C1 1.472(4) . ? O2 C5 1.199(4) . ? O3 C13 1.218(4) . ? O4 C13 1.335(4) . ? O4 C14 1.471(5) . ? O5 C20 1.353(4) . ? O5 C16 1.478(4) . ? O6 C20 1.217(4) . ? O7 C28 1.206(4) . ? O8 C28 1.346(4) . ? O8 C29 1.458(4) . ? N1 C5 1.356(5) . ? N1 C6 1.450(4) . ? N2 C20 1.347(5) . ? N2 C21 1.456(4) . ? C1 C3 1.510(5) . ? C1 C4 1.509(5) . ? C1 C2 1.521(6) . ? C6 C11 1.495(5) . ? C6 C7 1.535(5) . ? C7 C8 1.522(5) . ? C8 C10 1.520(5) . ? C8 C9 1.521(5) . ? C11 C12 1.323(4) . ? C12 C13 1.462(5) . ? C14 C15 1.479(6) . ? C16 C19 1.505(5) . ? C16 C18 1.522(5) . ? C16 C17 1.522(4) . ? C21 C26 1.502(5) . ? C21 C22 1.535(5) . ? C22 C23 1.521(5) . ? C23 C24 1.516(5) . ? C23 C25 1.528(5) . ? C26 C27 1.324(4) . ? C27 C28 1.472(5) . ? C29 C30 1.501(5) . ? 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 O1 C1 119.5(3) . . ? C13 O4 C14 117.1(3) . . ? C20 O5 C16 120.3(3) . . ? C28 O8 C29 115.7(3) . . ? C5 N1 C6 121.9(3) . . ? C20 N2 C21 121.4(3) . . ? O1 C1 C3 110.5(3) . . ? O1 C1 C4 110.5(3) . . ? C3 C1 C4 111.6(3) . . ? O1 C1 C2 102.4(3) . . ? C3 C1 C2 110.6(3) . . ? C4 C1 C2 110.8(3) . . ? O2 C5 N1 124.4(3) . . ? O2 C5 O1 126.3(4) . . ? N1 C5 O1 109.3(3) . . ? N1 C6 C11 112.6(3) . . ? N1 C6 C7 109.3(3) . . ? C11 C6 C7 110.9(3) . . ? C8 C7 C6 114.4(3) . . ? C7 C8 C10 110.3(3) . . ? C7 C8 C9 112.0(3) . . ? C10 C8 C9 109.8(4) . . ? C12 C11 C6 128.3(3) . . ? C11 C12 C13 121.4(4) . . ? O3 C13 O4 123.1(4) . . ? O3 C13 C12 125.1(4) . . ? O4 C13 C12 111.8(4) . . ? O4 C14 C15 109.4(3) . . ? O5 C16 C19 109.5(3) . . ? O5 C16 C18 102.5(3) . . ? C19 C16 C18 111.3(3) . . ? O5 C16 C17 110.6(3) . . ? C19 C16 C17 112.1(3) . . ? C18 C16 C17 110.4(3) . . ? O6 C20 N2 124.5(3) . . ? O6 C20 O5 125.3(4) . . ? N2 C20 O5 110.2(4) . . ? N2 C21 C26 113.3(3) . . ? N2 C21 C22 109.5(3) . . ? C26 C21 C22 110.9(3) . . ? C23 C22 C21 116.0(3) . . ? C24 C23 C22 111.7(3) . . ? C24 C23 C25 109.2(3) . . ? C22 C23 C25 110.5(3) . . ? C27 C26 C21 127.8(3) . . ? C26 C27 C28 121.3(3) . . ? O7 C28 O8 123.8(3) . . ? O7 C28 C27 125.2(4) . . ? O8 C28 C27 111.0(4) . . ? O8 C29 C30 111.3(3) . . ? _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 24.28 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 0.110 _refine_diff_density_min -0.130 _refine_diff_density_rms 0.027 # Attachment 'Boc-Ala-dgVal-OEt.cif' data_hngbadgv _database_code_depnum_ccdc_archive 'CCDC 825100' #TrackingRef 'Boc-Ala-dgVal-OEt.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ;(S,E)-ethyl 4-((S)-2-(tert-butoxycarbonylamino)propanamido) -5-methylhex-2-enoate Chemical Formula: C17H30N2O5 ; _chemical_name_common 'alpha gamma mixed peptide' _chemical_formula_moiety 'C102 H180 N12 O30' _chemical_formula_sum 'C102 H180 N12 O30' _chemical_compound_source synthesis _exptl_crystal_recrystallization_method EtOAc/hexane _chemical_melting_point ? _exptl_crystal_description 'square block' _exptl_crystal_colour colorless _diffrn_ambient_temperature 100(2) _diffrn_ambient_pressure 101.325 _chemical_formula_weight 2054.58 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 triclinic _symmetry_space_group_name_H-M 'P 1' _symmetry_int_tables_number 1 _chemical_absolute_configuration syn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 13.3376(19) _cell_length_b 14.030(2) _cell_length_c 17.956(3) _cell_angle_alpha 88.064(5) _cell_angle_beta 70.670(4) _cell_angle_gamma 73.874(5) _cell_volume 3039.6(7) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.122 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1116 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.980 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Graphite monochromator' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 54826 _diffrn_reflns_av_R_equivalents 0.0718 _diffrn_reflns_av_sigmaI/netI 0.1482 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 28.28 _reflns_number_total 25408 _reflns_number_gt 12742 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1203P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1.1(10) _refine_ls_number_reflns 25408 _refine_ls_number_parameters 1339 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1817 _refine_ls_R_factor_gt 0.0881 _refine_ls_wR_factor_ref 0.2449 _refine_ls_wR_factor_gt 0.1946 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _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 0.6049(3) 0.6036(3) -0.1355(2) 0.0354(9) Uani 1 1 d . . . O2 O 0.7028(3) 0.6527(3) -0.0694(2) 0.0384(9) Uani 1 1 d . . . O3 O 0.4550(3) 0.7772(3) 0.06944(19) 0.0338(8) Uani 1 1 d . . . O4 O 0.4697(4) 1.1321(3) 0.2821(3) 0.0680(14) Uani 1 1 d . . . O5 O 0.5305(3) 1.1921(3) 0.1633(2) 0.0480(10) Uani 1 1 d . . . O6 O 0.9335(3) 0.5518(3) -0.0229(2) 0.0461(10) Uani 1 1 d . . . O7 O 1.0785(3) 0.6192(3) -0.0678(2) 0.0439(10) Uani 1 1 d . . . O8 O 0.7805(3) 0.8871(3) -0.0255(2) 0.0394(9) Uani 1 1 d . . . O9 O 0.8398(4) 1.2216(3) 0.1748(2) 0.0595(12) Uani 1 1 d . . . O10 O 0.7914(3) 1.0792(3) 0.1866(2) 0.0472(10) Uani 1 1 d . . . O11 O 0.9170(3) 0.9813(3) 0.4556(2) 0.0460(10) Uani 1 1 d . . . O12 O 0.7783(3) 0.9065(3) 0.4898(2) 0.0414(9) Uani 1 1 d . . . O13 O 1.0876(3) 0.6419(3) 0.4178(2) 0.0413(9) Uani 1 1 d . . . O14 O 1.0104(5) 0.3287(4) 0.6927(3) 0.0761(15) Uani 1 1 d . . . O15 O 1.0597(4) 0.4694(4) 0.6660(3) 0.0685(13) Uani 1 1 d . . . O16 O 0.2407(3) 0.9379(3) 0.1993(2) 0.0360(8) Uani 1 1 d . . . O17 O 0.1499(3) 0.8813(3) 0.3165(2) 0.0351(8) Uani 1 1 d . . . O18 O 0.4137(3) 0.7564(3) 0.32992(19) 0.0328(8) Uani 1 1 d . . . O19 O 0.4041(4) 0.4391(4) 0.5907(3) 0.0683(13) Uani 1 1 d . . . O20 O 0.3856(4) 0.3628(3) 0.4922(3) 0.0694(14) Uani 1 1 d . . . O21 O 0.2519(3) 0.9472(3) 0.6889(2) 0.0358(8) Uani 1 1 d . . . O22 O 0.1457(3) 0.9023(3) 0.8057(2) 0.0372(9) Uani 1 1 d . . . O23 O 0.3800(3) 0.7901(3) 0.8443(2) 0.0341(8) Uani 1 1 d . . . O24 O 0.3082(4) 0.4624(3) 1.1159(3) 0.0583(12) Uani 1 1 d . . . O25 O 0.3382(3) 0.3865(3) 1.0008(2) 0.0467(10) Uani 1 1 d . . . O26 O 0.6301(3) 0.5670(3) 0.3637(2) 0.0384(9) Uani 1 1 d . . . O27 O 0.7298(3) 0.6191(3) 0.4271(2) 0.0360(9) Uani 1 1 d . . . O28 O 0.4763(3) 0.7496(3) 0.5710(2) 0.0342(8) Uani 1 1 d . . . O29 O 0.5291(4) 1.0871(3) 0.7865(2) 0.0513(11) Uani 1 1 d . . . O30 O 0.5148(4) 1.1606(3) 0.6761(2) 0.0502(11) Uani 1 1 d . . . N1 N 0.5621(3) 0.7621(3) -0.0974(2) 0.0287(10) Uani 1 1 d . . . H1 H 0.5189 0.7737 -0.1251 0.034 Uiso 1 1 calc R . . N2 N 0.5910(3) 0.8395(3) 0.0785(2) 0.0308(10) Uani 1 1 d . . . H2 H 0.6479 0.8583 0.0515 0.037 Uiso 1 1 calc R . . N3 N 0.9107(4) 0.6947(3) -0.0787(3) 0.0399(11) Uani 1 1 d . . . H3 H 0.8436 0.6915 -0.0658 0.048 Uiso 1 1 calc R . . N4 N 0.9197(4) 0.9495(3) -0.0918(2) 0.0356(10) Uani 1 1 d . . . H4 H 0.9877 0.9371 -0.1220 0.043 Uiso 1 1 calc R . . N5 N 0.9509(4) 0.8287(3) 0.4085(3) 0.0376(11) Uani 1 1 d . . . H5 H 1.0180 0.8320 0.3890 0.045 Uiso 1 1 calc R . . N6 N 0.9551(4) 0.5685(3) 0.4249(3) 0.0371(11) Uani 1 1 d . . . H6 H 0.8896 0.5764 0.4231 0.045 Uiso 1 1 calc R . . N7 N 0.2924(3) 0.7784(3) 0.2215(2) 0.0298(10) Uani 1 1 d . . . H7 H 0.3330 0.7684 0.1724 0.036 Uiso 1 1 calc R . . N8 N 0.2723(3) 0.7055(3) 0.4145(2) 0.0292(10) Uani 1 1 d . . . H8 H 0.2158 0.6851 0.4184 0.035 Uiso 1 1 calc R . . N9 N 0.2926(3) 0.7905(3) 0.7213(2) 0.0288(10) Uani 1 1 d . . . H9 H 0.3387 0.7766 0.6739 0.035 Uiso 1 1 calc R . . N10 N 0.2443(3) 0.7256(3) 0.9210(2) 0.0317(10) Uani 1 1 d . . . H10 H 0.1929 0.6999 0.9210 0.038 Uiso 1 1 calc R . . N11 N 0.5848(3) 0.7250(3) 0.4036(2) 0.0298(10) Uani 1 1 d . . . H11 H 0.5399 0.7346 0.3773 0.036 Uiso 1 1 calc R . . N12 N 0.6136(3) 0.8121(3) 0.5769(2) 0.0296(10) Uani 1 1 d . . . H12 H 0.6652 0.8376 0.5499 0.036 Uiso 1 1 calc R . . C1 C 0.6536(5) 0.4991(4) -0.1300(3) 0.0411(14) Uani 1 1 d . . . C2 C 0.6221(5) 0.4755(5) -0.0419(4) 0.0495(15) Uani 1 1 d . . . H2A H 0.5429 0.4951 -0.0180 0.074 Uiso 1 1 calc R . . H2B H 0.6533 0.5114 -0.0152 0.074 Uiso 1 1 calc R . . H2C H 0.6505 0.4055 -0.0379 0.074 Uiso 1 1 calc R . . C3 C 0.7789(5) 0.4691(5) -0.1709(4) 0.0596(18) Uani 1 1 d . . . H3A H 0.8125 0.4966 -0.1405 0.089 Uiso 1 1 calc R . . H3B H 0.7959 0.4940 -0.2228 0.089 Uiso 1 1 calc R . . H3C H 0.8070 0.3980 -0.1753 0.089 Uiso 1 1 calc R . . C4 C 0.5987(6) 0.4493(5) -0.1719(4) 0.0550(17) Uani 1 1 d . . . H4A H 0.6137 0.4692 -0.2253 0.082 Uiso 1 1 calc R . . H4B H 0.5202 0.4686 -0.1447 0.082 Uiso 1 1 calc R . . H4C H 0.6274 0.3784 -0.1724 0.082 Uiso 1 1 calc R . . C5 C 0.6284(4) 0.6722(4) -0.0991(3) 0.0303(12) Uani 1 1 d . . . C6 C 0.5635(4) 0.8407(4) -0.0478(3) 0.0307(12) Uani 1 1 d . . . H6A H 0.6381 0.8491 -0.0649 0.037 Uiso 1 1 calc R . . C7 C 0.4824(5) 0.9377(4) -0.0527(3) 0.0413(14) Uani 1 1 d . . . H7A H 0.4118 0.9270 -0.0457 0.062 Uiso 1 1 calc R . . H7B H 0.5091 0.9632 -0.1035 0.062 Uiso 1 1 calc R . . H7C H 0.4744 0.9846 -0.0120 0.062 Uiso 1 1 calc R . . C8 C 0.5317(4) 0.8136(4) 0.0397(3) 0.0299(11) Uani 1 1 d . . . C9 C 0.5647(4) 0.8376(4) 0.1646(3) 0.0349(13) Uani 1 1 d . . . H9A H 0.5002 0.8120 0.1859 0.042 Uiso 1 1 calc R . . C10 C 0.6600(4) 0.7683(4) 0.1867(3) 0.0406(14) Uani 1 1 d . . . H10A H 0.6391 0.7738 0.2445 0.049 Uiso 1 1 calc R . . C11 C 0.7689(4) 0.7947(5) 0.1524(3) 0.0442(14) Uani 1 1 d . . . H11A H 0.7971 0.7808 0.0961 0.066 Uiso 1 1 calc R . . H11B H 0.8215 0.7558 0.1753 0.066 Uiso 1 1 calc R . . H11C H 0.7567 0.8640 0.1642 0.066 Uiso 1 1 calc R . . C12 C 0.6764(5) 0.6621(5) 0.1626(4) 0.0607(18) Uani 1 1 d . . . H12A H 0.7029 0.6531 0.1059 0.091 Uiso 1 1 calc R . . H12B H 0.6071 0.6463 0.1833 0.091 Uiso 1 1 calc R . . H12C H 0.7295 0.6190 0.1830 0.091 Uiso 1 1 calc R . . C13 C 0.5336(4) 0.9414(5) 0.2010(3) 0.0403(14) Uani 1 1 d . . . H13 H 0.5055 0.9478 0.2560 0.048 Uiso 1 1 calc R . . C14 C 0.5406(4) 1.0245(5) 0.1658(3) 0.0399(13) Uani 1 1 d . . . H14 H 0.5667 1.0222 0.1108 0.048 Uiso 1 1 calc R . . C15 C 0.5093(4) 1.1193(5) 0.2093(4) 0.0452(15) Uani 1 1 d . . . C16 C 0.5016(6) 1.2908(5) 0.2009(4) 0.0547(17) Uani 1 1 d . . . H16A H 0.5221 1.2864 0.2482 0.066 Uiso 1 1 calc R . . H16B H 0.4224 1.3215 0.2158 0.066 Uiso 1 1 calc R . . C17 C 0.5640(5) 1.3523(5) 0.1419(4) 0.0593(18) Uani 1 1 d . . . H17A H 0.5411 1.3582 0.0962 0.089 Uiso 1 1 calc R . . H17B H 0.6421 1.3203 0.1264 0.089 Uiso 1 1 calc R . . H17C H 0.5481 1.4173 0.1660 0.089 Uiso 1 1 calc R . . C18 C 0.9900(5) 0.4662(4) 0.0120(4) 0.0450(15) Uani 1 1 d . . . C19 C 0.9009(6) 0.4129(5) 0.0435(5) 0.0630(18) Uani 1 1 d . . . H19A H 0.8866 0.3879 0.0001 0.094 Uiso 1 1 calc R . . H19B H 0.8341 0.4585 0.0772 0.094 Uiso 1 1 calc R . . H19C H 0.9256 0.3586 0.0732 0.094 Uiso 1 1 calc R . . C20 C 1.0163(5) 0.5026(5) 0.0803(4) 0.0538(16) Uani 1 1 d . . . H20A H 0.9506 0.5478 0.1156 0.081 Uiso 1 1 calc R . . H20B H 1.0727 0.5361 0.0601 0.081 Uiso 1 1 calc R . . H20C H 1.0421 0.4469 0.1084 0.081 Uiso 1 1 calc R . . C21 C 1.0888(6) 0.4017(5) -0.0487(4) 0.0606(18) Uani 1 1 d . . . H21A H 1.1433 0.4371 -0.0689 0.091 Uiso 1 1 calc R . . H21B H 1.0678 0.3831 -0.0911 0.091 Uiso 1 1 calc R . . H21C H 1.1192 0.3430 -0.0254 0.091 Uiso 1 1 calc R . . C22 C 0.9826(5) 0.6222(4) -0.0579(3) 0.0385(13) Uani 1 1 d . . . C23 C 0.9368(5) 0.7769(4) -0.1207(3) 0.0383(13) Uani 1 1 d . . . H23 H 1.0164 0.7677 -0.1336 0.046 Uiso 1 1 calc R . . C24 C 0.9128(7) 0.7790(5) -0.1990(3) 0.065(2) Uani 1 1 d . . . H24A H 0.8346 0.7923 -0.1880 0.098 Uiso 1 1 calc R . . H24B H 0.9507 0.7159 -0.2282 0.098 Uiso 1 1 calc R . . H24C H 0.9383 0.8303 -0.2297 0.098 Uiso 1 1 calc R . . C25 C 0.8773(5) 0.8732(4) -0.0747(3) 0.0368(13) Uani 1 1 d . . . C26 C 0.8609(5) 1.0516(4) -0.0639(3) 0.0402(14) Uani 1 1 d . . . H26 H 0.9107 1.0918 -0.0899 0.048 Uiso 1 1 calc R . . C27 C 0.7531(5) 1.0926(4) -0.0856(3) 0.0447(14) Uani 1 1 d . . . H27 H 0.6997 1.0574 -0.0560 0.054 Uiso 1 1 calc R . . C28 C 0.7018(7) 1.2011(5) -0.0625(5) 0.073(2) Uani 1 1 d . . . H28A H 0.6411 1.2256 -0.0820 0.110 Uiso 1 1 calc R . . H28B H 0.7562 1.2362 -0.0848 0.110 Uiso 1 1 calc R . . H28C H 0.6754 1.2112 -0.0059 0.110 Uiso 1 1 calc R . . C29 C 0.7744(6) 1.0743(6) -0.1730(4) 0.070(2) Uani 1 1 d . . . H29A H 0.8292 1.1056 -0.2034 0.105 Uiso 1 1 calc R . . H29B H 0.7069 1.1016 -0.1842 0.105 Uiso 1 1 calc R . . H29C H 0.8008 1.0041 -0.1867 0.105 Uiso 1 1 calc R . . C30 C 0.8377(4) 1.0645(4) 0.0245(3) 0.0377(13) Uani 1 1 d . . . H30 H 0.8044 1.0208 0.0566 0.045 Uiso 1 1 calc R . . C31 C 0.8609(5) 1.1321(4) 0.0589(3) 0.0442(14) Uani 1 1 d . . . H31 H 0.8996 1.1723 0.0264 0.053 Uiso 1 1 calc R . . C32 C 0.8310(5) 1.1500(4) 0.1449(3) 0.0443(14) Uani 1 1 d . . . C33 C 0.7562(5) 1.0952(5) 0.2726(3) 0.0505(16) Uani 1 1 d . . . H33A H 0.6891 1.1500 0.2913 0.061 Uiso 1 1 calc R . . H33B H 0.8134 1.1115 0.2875 0.061 Uiso 1 1 calc R . . C34 C 0.7358(7) 1.0029(5) 0.3083(4) 0.0654(19) Uani 1 1 d . . . H34A H 0.8031 0.9495 0.2907 0.098 Uiso 1 1 calc R . . H34B H 0.6801 0.9867 0.2924 0.098 Uiso 1 1 calc R . . H34C H 0.7109 1.0124 0.3649 0.098 Uiso 1 1 calc R . . C35 C 0.8547(5) 1.0685(4) 0.5122(3) 0.0409(13) Uani 1 1 d . . . C36 C 0.7496(5) 1.1248(5) 0.4953(4) 0.0524(16) Uani 1 1 d . . . H36A H 0.6981 1.0857 0.5088 0.079 Uiso 1 1 calc R . . H36B H 0.7678 1.1372 0.4402 0.079 Uiso 1 1 calc R . . H36C H 0.7168 1.1869 0.5264 0.079 Uiso 1 1 calc R . . C37 C 0.9355(5) 1.1315(5) 0.4923(4) 0.0583(18) Uani 1 1 d . . . H37A H 0.9494 1.1494 0.4385 0.087 Uiso 1 1 calc R . . H37B H 1.0038 1.0941 0.4989 0.087 Uiso 1 1 calc R . . H37C H 0.9042 1.1906 0.5270 0.087 Uiso 1 1 calc R . . C38 C 0.8322(5) 1.0373(5) 0.5961(3) 0.0518(16) Uani 1 1 d . . . H38A H 0.9006 1.0004 0.6029 0.078 Uiso 1 1 calc R . . H38B H 0.7827 0.9963 0.6067 0.078 Uiso 1 1 calc R . . H38C H 0.7990 1.0953 0.6321 0.078 Uiso 1 1 calc R . . C39 C 0.8760(4) 0.9046(4) 0.4540(3) 0.0342(12) Uani 1 1 d . . . C40 C 0.9268(5) 0.7398(4) 0.3896(3) 0.0382(13) Uani 1 1 d . . . H40 H 0.8483 0.7460 0.4177 0.046 Uiso 1 1 calc R . . C41 C 0.9486(7) 0.7283(5) 0.3006(4) 0.066(2) Uani 1 1 d . . . H41A H 1.0236 0.7279 0.2720 0.099 Uiso 1 1 calc R . . H41B H 0.8987 0.7829 0.2856 0.099 Uiso 1 1 calc R . . H41C H 0.9370 0.6670 0.2883 0.099 Uiso 1 1 calc R . . C42 C 0.9958(4) 0.6468(4) 0.4138(3) 0.0372(13) Uani 1 1 d . . . C43 C 1.0168(5) 0.4693(4) 0.4399(4) 0.0480(16) Uani 1 1 d . . . H43 H 0.9704 0.4254 0.4417 0.058 Uiso 1 1 calc R . . C44 C 1.1284(5) 0.4234(5) 0.3735(4) 0.0543(17) Uani 1 1 d . . . H44 H 1.1760 0.4663 0.3710 0.065 Uiso 1 1 calc R . . C45 C 1.1866(6) 0.3214(5) 0.3917(5) 0.071(2) Uani 1 1 d . . . H45A H 1.2514 0.2924 0.3472 0.106 Uiso 1 1 calc R . . H45B H 1.1375 0.2801 0.4025 0.106 Uiso 1 1 calc R . . H45C H 1.2079 0.3269 0.4371 0.106 Uiso 1 1 calc R . . C46 C 1.1121(6) 0.4231(7) 0.2933(4) 0.077(2) Uani 1 1 d . . . H46A H 1.0712 0.3769 0.2920 0.116 Uiso 1 1 calc R . . H46B H 1.1830 0.4036 0.2522 0.116 Uiso 1 1 calc R . . H46C H 1.0717 0.4885 0.2853 0.116 Uiso 1 1 calc R . . C47 C 1.0309(5) 0.4683(4) 0.5189(4) 0.0450(15) Uani 1 1 d . . . H47 H 1.0611 0.5156 0.5308 0.054 Uiso 1 1 calc R . . C48 C 1.0037(5) 0.4052(5) 0.5736(4) 0.0531(16) Uani 1 1 d . . . H48 H 0.9685 0.3614 0.5627 0.064 Uiso 1 1 calc R . . C49 C 1.0238(5) 0.3975(5) 0.6499(4) 0.0547(17) Uani 1 1 d . . . C50 C 1.0813(7) 0.4672(7) 0.7411(4) 0.079(2) Uani 1 1 d . . . H50A H 1.0121 0.4920 0.7844 0.094 Uiso 1 1 calc R . . H50B H 1.1161 0.3994 0.7503 0.094 Uiso 1 1 calc R . . C51 C 1.1539(6) 0.5291(6) 0.7371(4) 0.0639(19) Uani 1 1 d . . . H51A H 1.1225 0.5941 0.7225 0.096 Uiso 1 1 calc R . . H51B H 1.2252 0.4997 0.6984 0.096 Uiso 1 1 calc R . . H51C H 1.1620 0.5344 0.7879 0.096 Uiso 1 1 calc R . . C52 C 0.1786(5) 1.0417(4) 0.2220(3) 0.0427(14) Uani 1 1 d . . . C53 C 0.0552(5) 1.0554(5) 0.2373(4) 0.0545(16) Uani 1 1 d . . . H53A H 0.0241 1.0276 0.2863 0.082 Uiso 1 1 calc R . . H53B H 0.0467 1.0221 0.1949 0.082 Uiso 1 1 calc R . . H53C H 0.0175 1.1250 0.2404 0.082 Uiso 1 1 calc R . . C54 C 0.2281(6) 1.0932(4) 0.1486(4) 0.0535(16) Uani 1 1 d . . . H54A H 0.2131 1.0703 0.1047 0.080 Uiso 1 1 calc R . . H54B H 0.3067 1.0780 0.1369 0.080 Uiso 1 1 calc R . . H54C H 0.1956 1.1638 0.1580 0.080 Uiso 1 1 calc R . . C55 C 0.2008(5) 1.0764(5) 0.2931(4) 0.0542(17) Uani 1 1 d . . . H55A H 0.2791 1.0638 0.2813 0.081 Uiso 1 1 calc R . . H55B H 0.1718 1.0410 0.3381 0.081 Uiso 1 1 calc R . . H55C H 0.1653 1.1464 0.3047 0.081 Uiso 1 1 calc R . . C56 C 0.2234(4) 0.8669(4) 0.2504(3) 0.0326(12) Uani 1 1 d . . . C57 C 0.2975(4) 0.6981(4) 0.2752(3) 0.0302(11) Uani 1 1 d . . . H57 H 0.2235 0.6886 0.2975 0.036 Uiso 1 1 calc R . . C58 C 0.3774(5) 0.6009(4) 0.2312(3) 0.0374(13) Uani 1 1 d . . . H58A H 0.4507 0.6085 0.2094 0.056 Uiso 1 1 calc R . . H58B H 0.3544 0.5842 0.1893 0.056 Uiso 1 1 calc R . . H58C H 0.3776 0.5488 0.2672 0.056 Uiso 1 1 calc R . . C59 C 0.3320(4) 0.7235(4) 0.3431(3) 0.0275(11) Uani 1 1 d . . . C60 C 0.2953(4) 0.7176(4) 0.4869(3) 0.0315(12) Uani 1 1 d . . . H60 H 0.3589 0.7449 0.4720 0.038 Uiso 1 1 calc R . . C61 C 0.1983(4) 0.7955(5) 0.5464(3) 0.0411(14) Uani 1 1 d . . . H61 H 0.2209 0.8054 0.5915 0.049 Uiso 1 1 calc R . . C62 C 0.0933(5) 0.7605(5) 0.5777(3) 0.0511(16) Uani 1 1 d . . . H62A H 0.0674 0.7533 0.5349 0.077 Uiso 1 1 calc R . . H62B H 0.0370 0.8087 0.6172 0.077 Uiso 1 1 calc R . . H62C H 0.1100 0.6977 0.6006 0.077 Uiso 1 1 calc R . . C63 C 0.1739(5) 0.8946(5) 0.5096(4) 0.0507(16) Uani 1 1 d . . . H63A H 0.1460 0.8882 0.4677 0.076 Uiso 1 1 calc R . . H63B H 0.2407 0.9144 0.4886 0.076 Uiso 1 1 calc R . . H63C H 0.1196 0.9439 0.5491 0.076 Uiso 1 1 calc R . . C64 C 0.3293(4) 0.6223(4) 0.5204(3) 0.0391(13) Uani 1 1 d . . . H64 H 0.3486 0.6251 0.5654 0.047 Uiso 1 1 calc R . . C65 C 0.3358(5) 0.5346(5) 0.4952(3) 0.0440(14) Uani 1 1 d . . . H65 H 0.3145 0.5294 0.4515 0.053 Uiso 1 1 calc R . . C66 C 0.3759(6) 0.4410(5) 0.5326(4) 0.0571(17) Uani 1 1 d . . . C67 C 0.4355(8) 0.2677(5) 0.5195(5) 0.081(2) Uani 1 1 d . . . H67A H 0.5013 0.2707 0.5302 0.097 Uiso 1 1 calc R . . H67B H 0.3835 0.2540 0.5681 0.097 Uiso 1 1 calc R . . C68 C 0.4636(9) 0.1920(5) 0.4614(4) 0.088(3) Uani 1 1 d . . . H68A H 0.3984 0.1898 0.4507 0.132 Uiso 1 1 calc R . . H68B H 0.4949 0.1294 0.4798 0.132 Uiso 1 1 calc R . . H68C H 0.5167 0.2048 0.4140 0.132 Uiso 1 1 calc R . . C69 C 0.1935(5) 1.0534(4) 0.7046(3) 0.0427(14) Uani 1 1 d . . . C70 C 0.2543(6) 1.0973(5) 0.6304(4) 0.0585(17) Uani 1 1 d . . . H70A H 0.2440 1.0720 0.5853 0.088 Uiso 1 1 calc R . . H70B H 0.3319 1.0793 0.6235 0.088 Uiso 1 1 calc R . . H70C H 0.2254 1.1685 0.6356 0.088 Uiso 1 1 calc R . . C71 C 0.0729(5) 1.0734(5) 0.7114(4) 0.0491(15) Uani 1 1 d . . . H71A H 0.0354 1.0431 0.7569 0.074 Uiso 1 1 calc R . . H71B H 0.0686 1.0458 0.6647 0.074 Uiso 1 1 calc R . . H71C H 0.0384 1.1438 0.7168 0.074 Uiso 1 1 calc R . . C72 C 0.2068(6) 1.0922(5) 0.7783(4) 0.0595(18) Uani 1 1 d . . . H72A H 0.2835 1.0713 0.7740 0.089 Uiso 1 1 calc R . . H72B H 0.1642 1.0662 0.8243 0.089 Uiso 1 1 calc R . . H72C H 0.1809 1.1635 0.7828 0.089 Uiso 1 1 calc R . . C73 C 0.2256(4) 0.8804(4) 0.7431(3) 0.0320(12) Uani 1 1 d . . . C74 C 0.2878(4) 0.7149(4) 0.7783(3) 0.0293(11) Uani 1 1 d . . . H74 H 0.2145 0.7035 0.7941 0.035 Uiso 1 1 calc R . . C75 C 0.3747(4) 0.6192(4) 0.7428(3) 0.0375(13) Uani 1 1 d . . . H75A H 0.4469 0.6286 0.7308 0.056 Uiso 1 1 calc R . . H75B H 0.3662 0.5993 0.6951 0.056 Uiso 1 1 calc R . . H75C H 0.3667 0.5685 0.7797 0.056 Uiso 1 1 calc R . . C76 C 0.3069(4) 0.7484(4) 0.8521(3) 0.0277(11) Uani 1 1 d . . . C77 C 0.2576(4) 0.7416(4) 0.9969(3) 0.0370(13) Uani 1 1 d . . . H77 H 0.3249 0.7630 0.9850 0.044 Uiso 1 1 calc R . . C78 C 0.1609(4) 0.8267(4) 1.0503(3) 0.0414(14) Uani 1 1 d . . . H78 H 0.1788 0.8369 1.0976 0.050 Uiso 1 1 calc R . . C79 C 0.1503(5) 0.9224(4) 1.0096(3) 0.0446(14) Uani 1 1 d . . . H79A H 0.1273 0.9164 0.9651 0.067 Uiso 1 1 calc R . . H79B H 0.2206 0.9366 0.9918 0.067 Uiso 1 1 calc R . . H79C H 0.0963 0.9753 1.0460 0.067 Uiso 1 1 calc R . . C80 C 0.0502(5) 0.7990(5) 1.0780(3) 0.0509(16) Uani 1 1 d . . . H80A H 0.0255 0.7968 1.0337 0.076 Uiso 1 1 calc R . . H80B H -0.0046 0.8480 1.1175 0.076 Uiso 1 1 calc R . . H80C H 0.0609 0.7350 1.0998 0.076 Uiso 1 1 calc R . . C81 C 0.2769(4) 0.6473(4) 1.0363(3) 0.0387(13) Uani 1 1 d . . . H81 H 0.2762 0.6517 1.0881 0.046 Uiso 1 1 calc R . . C82 C 0.2950(4) 0.5586(4) 1.0056(3) 0.0392(13) Uani 1 1 d . . . H82 H 0.2963 0.5531 0.9538 0.047 Uiso 1 1 calc R . . C83 C 0.3135(4) 0.4666(4) 1.0472(4) 0.0420(14) Uani 1 1 d . . . C84 C 0.3560(7) 0.2908(5) 1.0344(4) 0.0651(19) Uani 1 1 d . . . H84A H 0.2926 0.2907 1.0806 0.078 Uiso 1 1 calc R . . H84B H 0.4209 0.2774 1.0506 0.078 Uiso 1 1 calc R . . C85 C 0.3719(8) 0.2132(5) 0.9744(4) 0.079(2) Uani 1 1 d . . . H85A H 0.4420 0.2053 0.9333 0.118 Uiso 1 1 calc R . . H85B H 0.3135 0.2326 0.9523 0.118 Uiso 1 1 calc R . . H85C H 0.3708 0.1514 0.9989 0.118 Uiso 1 1 calc R . . C86 C 0.6929(5) 0.4629(4) 0.3540(4) 0.0428(14) Uani 1 1 d . . . C87 C 0.6303(6) 0.4175(5) 0.3150(4) 0.0620(19) Uani 1 1 d . . . H87A H 0.6241 0.4526 0.2691 0.093 Uiso 1 1 calc R . . H87B H 0.5576 0.4225 0.3516 0.093 Uiso 1 1 calc R . . H87C H 0.6695 0.3488 0.2995 0.093 Uiso 1 1 calc R . . C88 C 0.6873(6) 0.4217(5) 0.4350(4) 0.0610(18) Uani 1 1 d . . . H88A H 0.6123 0.4429 0.4706 0.091 Uiso 1 1 calc R . . H88B H 0.7339 0.4460 0.4557 0.091 Uiso 1 1 calc R . . H88C H 0.7121 0.3504 0.4295 0.091 Uiso 1 1 calc R . . C89 C 0.8119(5) 0.4483(5) 0.3003(4) 0.0541(17) Uani 1 1 d . . . H89A H 0.8488 0.4799 0.3252 0.081 Uiso 1 1 calc R . . H89B H 0.8125 0.4772 0.2510 0.081 Uiso 1 1 calc R . . H89C H 0.8497 0.3785 0.2906 0.081 Uiso 1 1 calc R . . C90 C 0.6539(4) 0.6354(4) 0.4004(3) 0.0322(12) Uani 1 1 d . . . C91 C 0.5840(4) 0.8069(4) 0.4510(3) 0.0279(11) Uani 1 1 d . . . H91 H 0.6583 0.8161 0.4328 0.033 Uiso 1 1 calc R . . C92 C 0.5035(4) 0.9018(4) 0.4425(3) 0.0347(12) Uani 1 1 d . . . H92A H 0.4312 0.8924 0.4559 0.052 Uiso 1 1 calc R . . H92B H 0.5267 0.9203 0.3888 0.052 Uiso 1 1 calc R . . H92C H 0.5012 0.9535 0.4772 0.052 Uiso 1 1 calc R . . C93 C 0.5543(4) 0.7846(4) 0.5392(3) 0.0282(11) Uani 1 1 d . . . C94 C 0.5965(4) 0.8017(4) 0.6613(3) 0.0318(12) Uani 1 1 d . . . H94 H 0.5307 0.7780 0.6834 0.038 Uiso 1 1 calc R . . C95 C 0.6933(4) 0.7229(4) 0.6746(3) 0.0368(13) Uani 1 1 d . . . H95 H 0.6754 0.7173 0.7318 0.044 Uiso 1 1 calc R . . C96 C 0.7082(5) 0.6218(4) 0.6381(3) 0.0435(14) Uani 1 1 d . . . H96A H 0.7239 0.6254 0.5821 0.065 Uiso 1 1 calc R . . H96B H 0.6415 0.6022 0.6610 0.065 Uiso 1 1 calc R . . H96C H 0.7686 0.5738 0.6482 0.065 Uiso 1 1 calc R . . C97 C 0.8026(4) 0.7504(5) 0.6436(3) 0.0433(14) Uani 1 1 d . . . H97A H 0.8234 0.7547 0.5874 0.065 Uiso 1 1 calc R . . H97B H 0.8594 0.7004 0.6560 0.065 Uiso 1 1 calc R . . H97C H 0.7936 0.8135 0.6681 0.065 Uiso 1 1 calc R . . C98 C 0.5711(4) 0.9012(4) 0.7024(3) 0.0365(13) Uani 1 1 d . . . H98 H 0.5671 0.9008 0.7551 0.044 Uiso 1 1 calc R . . C99 C 0.5538(4) 0.9889(4) 0.6727(3) 0.0335(12) Uani 1 1 d . . . H99 H 0.5558 0.9923 0.6205 0.040 Uiso 1 1 calc R . . C100 C 0.5314(5) 1.0821(5) 0.7188(3) 0.0419(14) Uani 1 1 d . . . C101 C 0.4952(7) 1.2584(5) 0.7131(4) 0.066(2) Uani 1 1 d . . . H10B H 0.5153 1.3036 0.6724 0.079 Uiso 1 1 calc R . . H10C H 0.5413 1.2529 0.7458 0.079 Uiso 1 1 calc R . . C102 C 0.3769(7) 1.2987(6) 0.7624(5) 0.081(2) Uani 1 1 d . . . H10D H 0.3558 1.2519 0.8004 0.121 Uiso 1 1 calc R . . H10E H 0.3318 1.3099 0.7291 0.121 Uiso 1 1 calc R . . H10F H 0.3668 1.3603 0.7894 0.121 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 0.032(2) 0.045(2) 0.0303(19) 0.0017(17) -0.0100(17) -0.0143(18) O2 0.029(2) 0.050(2) 0.041(2) 0.0078(18) -0.0153(18) -0.0154(18) O3 0.0247(19) 0.055(2) 0.0241(18) 0.0016(16) 0.0006(15) -0.0244(18) O4 0.084(4) 0.075(3) 0.035(3) -0.013(2) 0.003(2) -0.034(3) O5 0.052(3) 0.058(3) 0.035(2) -0.001(2) -0.013(2) -0.017(2) O6 0.032(2) 0.046(2) 0.063(3) 0.007(2) -0.011(2) -0.0195(19) O7 0.023(2) 0.074(3) 0.043(2) 0.006(2) -0.0097(17) -0.0269(19) O8 0.025(2) 0.057(2) 0.030(2) 0.0053(17) 0.0053(16) -0.0184(18) O9 0.076(3) 0.062(3) 0.046(3) -0.004(2) -0.016(2) -0.032(3) O10 0.051(3) 0.058(3) 0.030(2) -0.0001(19) -0.0048(19) -0.023(2) O11 0.029(2) 0.055(2) 0.048(2) -0.0010(19) 0.0073(18) -0.0258(19) O12 0.024(2) 0.067(3) 0.031(2) 0.0077(18) 0.0020(16) -0.0244(19) O13 0.025(2) 0.067(3) 0.036(2) 0.0061(19) -0.0061(17) -0.0248(19) O14 0.094(4) 0.059(3) 0.069(3) 0.015(3) -0.015(3) -0.029(3) O15 0.085(4) 0.083(3) 0.057(3) 0.028(2) -0.028(3) -0.050(3) O16 0.031(2) 0.046(2) 0.0263(19) 0.0046(17) -0.0020(16) -0.0134(18) O17 0.0237(19) 0.053(2) 0.0246(19) 0.0038(16) 0.0004(16) -0.0152(17) O18 0.0252(19) 0.055(2) 0.0243(18) 0.0074(16) -0.0063(15) -0.0235(17) O19 0.074(3) 0.071(3) 0.049(3) 0.018(2) -0.016(3) -0.012(3) O20 0.095(4) 0.053(3) 0.046(3) 0.009(2) -0.006(3) -0.020(3) O21 0.028(2) 0.043(2) 0.031(2) 0.0069(17) -0.0010(16) -0.0134(17) O22 0.0200(19) 0.060(2) 0.0255(19) 0.0015(17) 0.0018(16) -0.0130(18) O23 0.0288(19) 0.053(2) 0.0300(19) 0.0133(16) -0.0120(16) -0.0252(18) O24 0.079(3) 0.060(3) 0.048(3) 0.014(2) -0.031(3) -0.030(2) O25 0.055(3) 0.040(2) 0.035(2) 0.0090(18) -0.005(2) -0.011(2) O26 0.030(2) 0.058(3) 0.033(2) -0.0049(17) -0.0110(17) -0.0188(19) O27 0.0222(19) 0.054(2) 0.034(2) -0.0027(17) -0.0080(16) -0.0142(17) O28 0.0211(18) 0.054(2) 0.0279(19) -0.0002(16) 0.0003(15) -0.0213(17) O29 0.065(3) 0.060(3) 0.031(2) -0.0020(19) -0.017(2) -0.020(2) O30 0.062(3) 0.048(3) 0.036(2) 0.001(2) -0.012(2) -0.012(2) N1 0.023(2) 0.042(3) 0.018(2) -0.0001(18) -0.0012(18) -0.011(2) N2 0.024(2) 0.057(3) 0.0146(19) 0.0056(18) -0.0009(17) -0.023(2) N3 0.027(3) 0.049(3) 0.040(3) 0.002(2) -0.006(2) -0.010(2) N4 0.024(2) 0.048(3) 0.029(2) 0.006(2) -0.0005(19) -0.014(2) N5 0.028(2) 0.047(3) 0.039(3) 0.001(2) -0.006(2) -0.017(2) N6 0.026(2) 0.042(3) 0.042(3) -0.003(2) -0.006(2) -0.013(2) N7 0.024(2) 0.045(3) 0.021(2) 0.0022(19) -0.0040(18) -0.014(2) N8 0.021(2) 0.048(3) 0.022(2) 0.0045(19) -0.0054(18) -0.017(2) N9 0.024(2) 0.045(3) 0.019(2) 0.0055(19) -0.0037(18) -0.015(2) N10 0.028(2) 0.055(3) 0.019(2) 0.0088(19) -0.0082(18) -0.022(2) N11 0.028(2) 0.048(3) 0.017(2) 0.0009(18) -0.0034(18) -0.020(2) N12 0.021(2) 0.054(3) 0.016(2) 0.0015(18) 0.0000(17) -0.023(2) C1 0.034(3) 0.044(4) 0.043(3) 0.001(3) -0.011(3) -0.009(3) C2 0.055(4) 0.048(4) 0.044(4) 0.013(3) -0.014(3) -0.016(3) C3 0.042(4) 0.061(4) 0.061(4) 0.003(3) -0.010(3) 0.000(3) C4 0.061(4) 0.046(4) 0.059(4) -0.006(3) -0.025(4) -0.010(3) C5 0.028(3) 0.041(3) 0.022(3) 0.000(2) -0.002(2) -0.017(3) C6 0.034(3) 0.043(3) 0.014(2) 0.003(2) -0.002(2) -0.019(3) C7 0.056(4) 0.045(3) 0.029(3) 0.007(2) -0.015(3) -0.021(3) C8 0.024(3) 0.043(3) 0.022(3) 0.000(2) -0.005(2) -0.012(2) C9 0.028(3) 0.063(4) 0.016(2) 0.004(2) -0.001(2) -0.024(3) C10 0.026(3) 0.064(4) 0.028(3) 0.011(3) -0.003(2) -0.013(3) C11 0.029(3) 0.074(4) 0.030(3) 0.004(3) -0.003(2) -0.025(3) C12 0.029(3) 0.076(5) 0.070(5) 0.025(4) -0.006(3) -0.018(3) C13 0.026(3) 0.072(4) 0.025(3) -0.005(3) -0.004(2) -0.020(3) C14 0.030(3) 0.059(4) 0.029(3) -0.001(3) -0.007(2) -0.014(3) C15 0.024(3) 0.066(4) 0.043(4) -0.009(3) -0.009(3) -0.009(3) C16 0.050(4) 0.055(4) 0.049(4) -0.014(3) -0.011(3) -0.003(3) C17 0.047(4) 0.068(5) 0.056(4) -0.008(3) -0.012(3) -0.010(3) C18 0.037(3) 0.038(3) 0.062(4) 0.015(3) -0.020(3) -0.011(3) C19 0.065(5) 0.053(4) 0.076(5) 0.020(4) -0.020(4) -0.030(4) C20 0.044(4) 0.077(5) 0.041(4) 0.012(3) -0.006(3) -0.029(4) C21 0.057(4) 0.056(4) 0.065(5) 0.002(3) -0.021(4) -0.007(4) C22 0.037(3) 0.044(3) 0.033(3) 0.000(3) -0.005(3) -0.017(3) C23 0.036(3) 0.037(3) 0.033(3) 0.008(3) -0.002(3) -0.008(3) C24 0.105(6) 0.062(4) 0.022(3) 0.000(3) -0.009(4) -0.025(4) C25 0.038(3) 0.049(3) 0.027(3) 0.012(2) -0.008(3) -0.024(3) C26 0.038(3) 0.055(4) 0.028(3) 0.007(3) -0.002(2) -0.025(3) C27 0.035(3) 0.048(4) 0.044(3) -0.001(3) -0.008(3) -0.007(3) C28 0.082(6) 0.070(5) 0.068(5) 0.000(4) -0.036(4) -0.007(4) C29 0.057(5) 0.096(6) 0.045(4) -0.010(4) -0.019(4) 0.000(4) C30 0.036(3) 0.044(3) 0.034(3) 0.003(2) -0.007(3) -0.018(3) C31 0.040(3) 0.052(4) 0.036(3) 0.005(3) -0.008(3) -0.011(3) C32 0.037(3) 0.049(4) 0.043(3) -0.006(3) -0.005(3) -0.014(3) C33 0.042(4) 0.068(4) 0.039(3) -0.005(3) -0.007(3) -0.018(3) C34 0.079(5) 0.071(5) 0.042(4) 0.010(3) -0.014(4) -0.022(4) C35 0.035(3) 0.045(3) 0.039(3) -0.002(3) -0.004(3) -0.015(3) C36 0.040(4) 0.063(4) 0.045(4) 0.002(3) -0.004(3) -0.012(3) C37 0.047(4) 0.047(4) 0.069(4) -0.009(3) 0.001(3) -0.017(3) C38 0.046(4) 0.070(4) 0.039(3) 0.004(3) -0.011(3) -0.019(3) C39 0.029(3) 0.042(3) 0.035(3) 0.007(3) -0.012(3) -0.014(3) C40 0.031(3) 0.049(3) 0.040(3) 0.005(3) -0.016(3) -0.016(3) C41 0.092(6) 0.072(5) 0.050(4) 0.010(3) -0.042(4) -0.028(4) C42 0.025(3) 0.055(4) 0.030(3) -0.008(3) 0.001(2) -0.020(3) C43 0.027(3) 0.044(4) 0.070(4) -0.010(3) -0.006(3) -0.015(3) C44 0.032(3) 0.060(4) 0.059(4) -0.016(3) 0.005(3) -0.016(3) C45 0.057(5) 0.064(5) 0.070(5) -0.016(4) -0.012(4) 0.008(4) C46 0.044(4) 0.109(6) 0.057(5) -0.020(4) 0.007(4) -0.014(4) C47 0.029(3) 0.038(3) 0.064(4) 0.009(3) -0.008(3) -0.012(3) C48 0.052(4) 0.055(4) 0.054(4) 0.002(3) -0.009(3) -0.028(3) C49 0.046(4) 0.048(4) 0.062(4) 0.003(3) -0.011(3) -0.009(3) C50 0.080(6) 0.127(7) 0.047(4) 0.032(4) -0.028(4) -0.053(5) C51 0.053(4) 0.091(5) 0.045(4) -0.001(4) -0.013(3) -0.020(4) C52 0.037(3) 0.044(4) 0.042(3) 0.004(3) -0.003(3) -0.014(3) C53 0.038(4) 0.058(4) 0.061(4) 0.009(3) -0.012(3) -0.009(3) C54 0.056(4) 0.041(4) 0.058(4) 0.011(3) -0.010(3) -0.016(3) C55 0.052(4) 0.058(4) 0.042(4) -0.008(3) 0.006(3) -0.024(3) C56 0.031(3) 0.044(3) 0.028(3) 0.010(3) -0.011(3) -0.019(3) C57 0.022(3) 0.050(3) 0.022(2) 0.004(2) -0.005(2) -0.017(2) C58 0.038(3) 0.045(3) 0.027(3) -0.001(2) -0.006(2) -0.012(3) C59 0.020(3) 0.039(3) 0.026(3) 0.003(2) -0.008(2) -0.011(2) C60 0.022(3) 0.050(3) 0.021(3) 0.001(2) -0.003(2) -0.013(2) C61 0.032(3) 0.071(4) 0.024(3) -0.004(3) -0.014(2) -0.013(3) C62 0.039(4) 0.080(5) 0.027(3) 0.004(3) 0.001(3) -0.020(3) C63 0.035(3) 0.060(4) 0.055(4) -0.011(3) -0.011(3) -0.015(3) C64 0.033(3) 0.053(4) 0.028(3) 0.004(3) 0.000(2) -0.019(3) C65 0.031(3) 0.060(4) 0.027(3) 0.013(3) 0.004(2) -0.009(3) C66 0.056(4) 0.054(4) 0.039(4) -0.003(3) 0.005(3) -0.005(3) C67 0.121(7) 0.052(5) 0.055(5) 0.017(4) -0.014(5) -0.020(5) C68 0.141(8) 0.055(5) 0.049(4) 0.007(4) -0.019(5) -0.014(5) C69 0.036(3) 0.046(4) 0.038(3) 0.002(3) 0.003(3) -0.020(3) C70 0.050(4) 0.053(4) 0.063(4) 0.016(3) -0.004(3) -0.019(3) C71 0.035(3) 0.053(4) 0.056(4) 0.004(3) -0.012(3) -0.012(3) C72 0.064(4) 0.057(4) 0.055(4) -0.005(3) -0.003(4) -0.033(4) C73 0.022(3) 0.044(3) 0.033(3) 0.003(3) -0.010(2) -0.012(3) C74 0.024(3) 0.043(3) 0.025(3) 0.007(2) -0.009(2) -0.016(2) C75 0.032(3) 0.049(3) 0.033(3) 0.007(3) -0.006(2) -0.021(3) C76 0.020(3) 0.042(3) 0.022(3) 0.006(2) -0.007(2) -0.012(2) C77 0.036(3) 0.060(4) 0.024(3) 0.005(3) -0.015(2) -0.024(3) C78 0.030(3) 0.065(4) 0.030(3) -0.005(3) -0.007(2) -0.016(3) C79 0.040(3) 0.052(4) 0.040(3) 0.000(3) -0.008(3) -0.017(3) C80 0.038(3) 0.085(5) 0.029(3) -0.001(3) -0.003(3) -0.025(3) C81 0.032(3) 0.057(4) 0.035(3) 0.003(3) -0.013(3) -0.023(3) C82 0.032(3) 0.056(4) 0.028(3) 0.011(3) -0.007(2) -0.015(3) C83 0.030(3) 0.057(4) 0.040(3) 0.002(3) -0.009(3) -0.018(3) C84 0.074(5) 0.055(4) 0.055(4) 0.005(3) -0.019(4) -0.006(4) C85 0.110(7) 0.048(4) 0.062(5) 0.004(4) -0.015(5) -0.011(4) C86 0.036(3) 0.044(4) 0.047(4) -0.004(3) -0.009(3) -0.016(3) C87 0.057(4) 0.053(4) 0.079(5) -0.014(4) -0.020(4) -0.021(3) C88 0.064(5) 0.062(4) 0.067(5) 0.017(4) -0.024(4) -0.034(4) C89 0.036(3) 0.070(4) 0.050(4) -0.014(3) -0.004(3) -0.015(3) C90 0.027(3) 0.045(3) 0.024(3) -0.001(2) -0.003(2) -0.017(3) C91 0.021(3) 0.043(3) 0.020(2) 0.004(2) -0.004(2) -0.014(2) C92 0.037(3) 0.039(3) 0.032(3) 0.004(2) -0.014(3) -0.014(3) C93 0.020(3) 0.043(3) 0.019(2) -0.005(2) -0.003(2) -0.009(2) C94 0.030(3) 0.052(3) 0.014(2) 0.009(2) -0.003(2) -0.020(3) C95 0.028(3) 0.058(4) 0.026(3) 0.006(2) -0.007(2) -0.016(3) C96 0.035(3) 0.059(4) 0.035(3) 0.006(3) -0.009(3) -0.015(3) C97 0.032(3) 0.071(4) 0.034(3) 0.013(3) -0.014(3) -0.025(3) C98 0.032(3) 0.054(4) 0.021(3) -0.003(3) -0.002(2) -0.017(3) C99 0.023(3) 0.049(4) 0.028(3) -0.005(3) -0.007(2) -0.011(3) C100 0.031(3) 0.053(4) 0.035(3) -0.004(3) -0.005(3) -0.009(3) C101 0.076(5) 0.053(4) 0.055(4) 0.003(3) -0.015(4) -0.005(4) C102 0.076(6) 0.085(6) 0.076(6) -0.004(5) -0.021(5) -0.019(5) _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 1.340(5) . ? O1 C1 1.444(7) . ? O2 C5 1.239(6) . ? O3 C8 1.225(5) . ? O4 C15 1.235(7) . ? O5 C15 1.325(7) . ? O5 C16 1.453(7) . ? O6 C22 1.358(6) . ? O6 C18 1.471(7) . ? O7 C22 1.221(6) . ? O8 C25 1.265(6) . ? O9 C32 1.206(6) . ? O10 C32 1.344(7) . ? O10 C33 1.464(7) . ? O11 C39 1.340(6) . ? O11 C35 1.477(7) . ? O12 C39 1.241(6) . ? O13 C42 1.234(6) . ? O14 C49 1.228(8) . ? O15 C49 1.307(7) . ? O15 C50 1.467(8) . ? O16 C56 1.346(6) . ? O16 C52 1.456(7) . ? O17 C56 1.244(6) . ? O18 C59 1.248(5) . ? O19 C66 1.219(8) . ? O20 C66 1.288(8) . ? O20 C67 1.464(9) . ? O21 C73 1.358(6) . ? O21 C69 1.465(7) . ? O22 C73 1.242(6) . ? O23 C76 1.237(5) . ? O24 C83 1.213(7) . ? O25 C83 1.320(7) . ? O25 C84 1.445(8) . ? O26 C90 1.344(6) . ? O26 C86 1.452(7) . ? O27 C90 1.222(6) . ? O28 C93 1.234(6) . ? O29 C100 1.211(7) . ? O30 C100 1.330(7) . ? O30 C101 1.462(8) . ? N1 C5 1.318(6) . ? N1 C6 1.449(6) . ? N1 H1 0.8600 . ? N2 C8 1.337(6) . ? N2 C9 1.469(6) . ? N2 H2 0.8600 . ? N3 C22 1.328(7) . ? N3 C23 1.418(7) . ? N3 H3 0.8600 . ? N4 C25 1.326(6) . ? N4 C26 1.444(7) . ? N4 H4 0.8600 . ? N5 C39 1.314(7) . ? N5 C40 1.449(7) . ? N5 H5 0.8600 . ? N6 C42 1.335(6) . ? N6 C43 1.474(7) . ? N6 H6 0.8600 . ? N7 C56 1.323(7) . ? N7 C57 1.460(7) . ? N7 H7 0.8600 . ? N8 C59 1.326(6) . ? N8 C60 1.456(6) . ? N8 H8 0.8600 . ? N9 C73 1.311(7) . ? N9 C74 1.447(6) . ? N9 H9 0.8600 . ? N10 C76 1.330(6) . ? N10 C77 1.463(6) . ? N10 H10 0.8600 . ? N11 C90 1.327(7) . ? N11 C91 1.448(6) . ? N11 H11 0.8600 . ? N12 C93 1.331(5) . ? N12 C94 1.465(6) . ? N12 H12 0.8600 . ? C1 C4 1.508(8) . ? C1 C3 1.526(8) . ? C1 C2 1.545(8) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C6 C7 1.505(8) . ? C6 C8 1.550(7) . ? C6 H6A 0.9800 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C9 C13 1.507(8) . ? C9 C10 1.530(8) . ? C9 H9A 0.9800 . ? C10 C12 1.502(9) . ? C10 C11 1.521(7) . ? C10 H10A 0.9800 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.319(8) . ? C13 H13 0.9300 . ? C14 C15 1.449(8) . ? C14 H14 0.9300 . ? C16 C17 1.521(9) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 C21 1.483(9) . ? C18 C19 1.521(8) . ? C18 C20 1.521(8) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C23 C25 1.478(8) . ? C23 C24 1.539(8) . ? C23 H23 0.9800 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C26 C30 1.520(7) . ? C26 C27 1.565(8) . ? C26 H26 0.9800 . ? C27 C28 1.494(9) . ? C27 C29 1.516(8) . ? C27 H27 0.9800 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 C31 1.306(7) . ? C30 H30 0.9300 . ? C31 C32 1.472(8) . ? C31 H31 0.9300 . ? C33 C34 1.479(9) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C35 C38 1.511(8) . ? C35 C37 1.525(8) . ? C35 C36 1.526(8) . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9600 . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 0.9600 . ? C40 C42 1.516(8) . ? C40 C41 1.533(8) . ? C40 H40 0.9800 . ? C41 H41A 0.9600 . ? C41 H41B 0.9600 . ? C41 H41C 0.9600 . ? C43 C47 1.491(9) . ? C43 C44 1.548(8) . ? C43 H43 0.9800 . ? C44 C45 1.509(10) . ? C44 C46 1.526(10) . ? C44 H44 0.9800 . ? C45 H45A 0.9600 . ? C45 H45B 0.9600 . ? C45 H45C 0.9600 . ? C46 H46A 0.9600 . ? C46 H46B 0.9600 . ? C46 H46C 0.9600 . ? C47 C48 1.328(8) . ? C47 H47 0.9300 . ? C48 C49 1.477(9) . ? C48 H48 0.9300 . ? C50 C51 1.455(10) . ? C50 H50A 0.9700 . ? C50 H50B 0.9700 . ? C51 H51A 0.9600 . ? C51 H51B 0.9600 . ? C51 H51C 0.9600 . ? C52 C54 1.523(8) . ? C52 C55 1.524(8) . ? C52 C53 1.534(8) . ? C53 H53A 0.9600 . ? C53 H53B 0.9600 . ? C53 H53C 0.9600 . ? C54 H54A 0.9600 . ? C54 H54B 0.9600 . ? C54 H54C 0.9600 . ? C55 H55A 0.9600 . ? C55 H55B 0.9600 . ? C55 H55C 0.9600 . ? C57 C59 1.521(6) . ? C57 C58 1.526(7) . ? C57 H57 0.9800 . ? C58 H58A 0.9600 . ? C58 H58B 0.9600 . ? C58 H58C 0.9600 . ? C60 C64 1.464(8) . ? C60 C61 1.545(7) . ? C60 H60 0.9800 . ? C61 C63 1.519(9) . ? C61 C62 1.536(8) . ? C61 H61 0.9800 . ? C62 H62A 0.9600 . ? C62 H62B 0.9600 . ? C62 H62C 0.9600 . ? C63 H63A 0.9600 . ? C63 H63B 0.9600 . ? C63 H63C 0.9600 . ? C64 C65 1.296(8) . ? C64 H64 0.9300 . ? C65 C66 1.499(9) . ? C65 H65 0.9300 . ? C67 C68 1.396(10) . ? C67 H67A 0.9700 . ? C67 H67B 0.9700 . ? C68 H68A 0.9600 . ? C68 H68B 0.9600 . ? C68 H68C 0.9600 . ? C69 C71 1.518(8) . ? C69 C70 1.523(8) . ? C69 C72 1.527(8) . ? C70 H70A 0.9600 . ? C70 H70B 0.9600 . ? C70 H70C 0.9600 . ? C71 H71A 0.9600 . ? C71 H71B 0.9600 . ? C71 H71C 0.9600 . ? C72 H72A 0.9600 . ? C72 H72B 0.9600 . ? C72 H72C 0.9600 . ? C74 C75 1.503(7) . ? C74 C76 1.541(6) . ? C74 H74 0.9800 . ? C75 H75A 0.9600 . ? C75 H75B 0.9600 . ? C75 H75C 0.9600 . ? C77 C81 1.478(8) . ? C77 C78 1.553(8) . ? C77 H77 0.9800 . ? C78 C79 1.500(8) . ? C78 C80 1.549(8) . ? C78 H78 0.9800 . ? C79 H79A 0.9600 . ? C79 H79B 0.9600 . ? C79 H79C 0.9600 . ? C80 H80A 0.9600 . ? C80 H80B 0.9600 . ? C80 H80C 0.9600 . ? C81 C82 1.306(7) . ? C81 H81 0.9300 . ? C82 C83 1.470(8) . ? C82 H82 0.9300 . ? C84 C85 1.479(10) . ? C84 H84A 0.9700 . ? C84 H84B 0.9700 . ? C85 H85A 0.9600 . ? C85 H85B 0.9600 . ? C85 H85C 0.9600 . ? C86 C87 1.519(8) . ? C86 C89 1.521(8) . ? C86 C88 1.533(9) . ? C87 H87A 0.9600 . ? C87 H87B 0.9600 . ? C87 H87C 0.9600 . ? C88 H88A 0.9600 . ? C88 H88B 0.9600 . ? C88 H88C 0.9600 . ? C89 H89A 0.9600 . ? C89 H89B 0.9600 . ? C89 H89C 0.9600 . ? C91 C92 1.500(7) . ? C91 C93 1.544(7) . ? C91 H91 0.9800 . ? C92 H92A 0.9600 . ? C92 H92B 0.9600 . ? C92 H92C 0.9600 . ? C94 C98 1.500(7) . ? C94 C95 1.530(8) . ? C94 H94 0.9800 . ? C95 C96 1.517(8) . ? C95 C97 1.532(7) . ? C95 H95 0.9800 . ? C96 H96A 0.9600 . ? C96 H96B 0.9600 . ? C96 H96C 0.9600 . ? C97 H97A 0.9600 . ? C97 H97B 0.9600 . ? C97 H97C 0.9600 . ? C98 C99 1.315(7) . ? C98 H98 0.9300 . ? C99 C100 1.475(8) . ? C99 H99 0.9300 . ? C101 C102 1.485(11) . ? C101 H10B 0.9700 . ? C101 H10C 0.9700 . ? C102 H10D 0.9600 . ? C102 H10E 0.9600 . ? C102 H10F 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 O1 C1 120.3(4) . . ? C15 O5 C16 117.9(5) . . ? C22 O6 C18 122.5(4) . . ? C32 O10 C33 115.5(4) . . ? C39 O11 C35 121.8(4) . . ? C49 O15 C50 116.6(6) . . ? C56 O16 C52 120.7(4) . . ? C66 O20 C67 115.8(6) . . ? C73 O21 C69 121.4(4) . . ? C83 O25 C84 118.3(5) . . ? C90 O26 C86 121.8(4) . . ? C100 O30 C101 117.7(5) . . ? C5 N1 C6 118.7(4) . . ? C5 N1 H1 120.6 . . ? C6 N1 H1 120.6 . . ? C8 N2 C9 123.8(4) . . ? C8 N2 H2 118.1 . . ? C9 N2 H2 118.1 . . ? C22 N3 C23 124.6(5) . . ? C22 N3 H3 117.7 . . ? C23 N3 H3 117.7 . . ? C25 N4 C26 125.3(5) . . ? C25 N4 H4 117.4 . . ? C26 N4 H4 117.4 . . ? C39 N5 C40 123.7(4) . . ? C39 N5 H5 118.2 . . ? C40 N5 H5 118.2 . . ? C42 N6 C43 123.3(4) . . ? C42 N6 H6 118.3 . . ? C43 N6 H6 118.3 . . ? C56 N7 C57 118.2(4) . . ? C56 N7 H7 120.9 . . ? C57 N7 H7 120.9 . . ? C59 N8 C60 124.9(4) . . ? C59 N8 H8 117.5 . . ? C60 N8 H8 117.5 . . ? C73 N9 C74 119.0(4) . . ? C73 N9 H9 120.5 . . ? C74 N9 H9 120.5 . . ? C76 N10 C77 124.1(4) . . ? C76 N10 H10 118.0 . . ? C77 N10 H10 118.0 . . ? C90 N11 C91 120.8(4) . . ? C90 N11 H11 119.6 . . ? C91 N11 H11 119.6 . . ? C93 N12 C94 124.1(4) . . ? C93 N12 H12 118.0 . . ? C94 N12 H12 118.0 . . ? O1 C1 C4 103.2(4) . . ? O1 C1 C3 111.4(5) . . ? C4 C1 C3 111.0(5) . . ? O1 C1 C2 109.0(5) . . ? C4 C1 C2 110.4(5) . . ? C3 C1 C2 111.6(5) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O2 C5 N1 124.1(4) . . ? O2 C5 O1 123.6(5) . . ? N1 C5 O1 112.3(4) . . ? N1 C6 C7 111.5(4) . . ? N1 C6 C8 110.0(4) . . ? C7 C6 C8 108.0(4) . . ? N1 C6 H6A 109.1 . . ? C7 C6 H6A 109.1 . . ? C8 C6 H6A 109.1 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O3 C8 N2 125.0(4) . . ? O3 C8 C6 121.6(4) . . ? N2 C8 C6 113.3(4) . . ? N2 C9 C13 110.3(4) . . ? N2 C9 C10 111.7(4) . . ? C13 C9 C10 111.3(4) . . ? N2 C9 H9A 107.8 . . ? C13 C9 H9A 107.8 . . ? C10 C9 H9A 107.8 . . ? C12 C10 C11 109.8(5) . . ? C12 C10 C9 110.6(4) . . ? C11 C10 C9 113.7(5) . . ? C12 C10 H10A 107.5 . . ? C11 C10 H10A 107.5 . . ? C9 C10 H10A 107.5 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C9 129.0(5) . . ? C14 C13 H13 115.5 . . ? C9 C13 H13 115.5 . . ? C13 C14 C15 122.6(5) . . ? C13 C14 H14 118.7 . . ? C15 C14 H14 118.7 . . ? O4 C15 O5 122.3(6) . . ? O4 C15 C14 124.4(6) . . ? O5 C15 C14 113.2(5) . . ? O5 C16 C17 107.8(5) . . ? O5 C16 H16A 110.1 . . ? C17 C16 H16A 110.1 . . ? O5 C16 H16B 110.1 . . ? C17 C16 H16B 110.1 . . ? H16A C16 H16B 108.5 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O6 C18 C21 111.4(5) . . ? O6 C18 C19 101.7(4) . . ? C21 C18 C19 110.6(5) . . ? O6 C18 C20 109.6(5) . . ? C21 C18 C20 113.1(5) . . ? C19 C18 C20 109.8(5) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C18 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C18 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O7 C22 N3 125.4(5) . . ? O7 C22 O6 124.6(5) . . ? N3 C22 O6 110.0(5) . . ? N3 C23 C25 113.2(4) . . ? N3 C23 C24 110.0(5) . . ? C25 C23 C24 110.0(5) . . ? N3 C23 H23 107.8 . . ? C25 C23 H23 107.8 . . ? C24 C23 H23 107.8 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O8 C25 N4 119.2(5) . . ? O8 C25 C23 120.6(4) . . ? N4 C25 C23 119.7(5) . . ? N4 C26 C30 110.0(4) . . ? N4 C26 C27 113.8(4) . . ? C30 C26 C27 111.7(4) . . ? N4 C26 H26 107.0 . . ? C30 C26 H26 107.0 . . ? C27 C26 H26 107.0 . . ? C28 C27 C29 109.6(6) . . ? C28 C27 C26 111.5(5) . . ? C29 C27 C26 111.9(5) . . ? C28 C27 H27 107.9 . . ? C29 C27 H27 107.9 . . ? C26 C27 H27 107.9 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C27 C29 H29A 109.5 . . ? C27 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C27 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C31 C30 C26 125.2(5) . . ? C31 C30 H30 117.4 . . ? C26 C30 H30 117.4 . . ? C30 C31 C32 125.5(6) . . ? C30 C31 H31 117.3 . . ? C32 C31 H31 117.3 . . ? O9 C32 O10 123.4(5) . . ? O9 C32 C31 123.5(6) . . ? O10 C32 C31 113.1(5) . . ? O10 C33 C34 108.2(5) . . ? O10 C33 H33A 110.1 . . ? C34 C33 H33A 110.1 . . ? O10 C33 H33B 110.1 . . ? C34 C33 H33B 110.1 . . ? H33A C33 H33B 108.4 . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? O11 C35 C38 110.4(5) . . ? O11 C35 C37 101.8(4) . . ? C38 C35 C37 111.1(5) . . ? O11 C35 C36 110.6(4) . . ? C38 C35 C36 113.0(5) . . ? C37 C35 C36 109.4(5) . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C35 C37 H37A 109.5 . . ? C35 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C35 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C35 C38 H38A 109.5 . . ? C35 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C35 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? O12 C39 N5 124.4(5) . . ? O12 C39 O11 123.8(5) . . ? N5 C39 O11 111.9(4) . . ? N5 C40 C42 112.2(4) . . ? N5 C40 C41 110.4(5) . . ? C42 C40 C41 108.6(5) . . ? N5 C40 H40 108.6 . . ? C42 C40 H40 108.6 . . ? C41 C40 H40 108.6 . . ? C40 C41 H41A 109.5 . . ? C40 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C40 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? O13 C42 N6 122.1(6) . . ? O13 C42 C40 121.6(5) . . ? N6 C42 C40 116.2(4) . . ? N6 C43 C47 111.9(4) . . ? N6 C43 C44 114.2(5) . . ? C47 C43 C44 111.5(5) . . ? N6 C43 H43 106.2 . . ? C47 C43 H43 106.2 . . ? C44 C43 H43 106.2 . . ? C45 C44 C46 112.3(6) . . ? C45 C44 C43 111.7(6) . . ? C46 C44 C43 110.8(5) . . ? C45 C44 H44 107.3 . . ? C46 C44 H44 107.3 . . ? C43 C44 H44 107.3 . . ? C44 C45 H45A 109.5 . . ? C44 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C44 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C44 C46 H46A 109.5 . . ? C44 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C44 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? C48 C47 C43 125.2(5) . . ? C48 C47 H47 117.4 . . ? C43 C47 H47 117.4 . . ? C47 C48 C49 126.5(6) . . ? C47 C48 H48 116.7 . . ? C49 C48 H48 116.7 . . ? O14 C49 O15 123.9(6) . . ? O14 C49 C48 122.7(6) . . ? O15 C49 C48 113.3(6) . . ? C51 C50 O15 108.6(6) . . ? C51 C50 H50A 110.0 . . ? O15 C50 H50A 110.0 . . ? C51 C50 H50B 110.0 . . ? O15 C50 H50B 110.0 . . ? H50A C50 H50B 108.3 . . ? C50 C51 H51A 109.5 . . ? C50 C51 H51B 109.5 . . ? H51A C51 H51B 109.5 . . ? C50 C51 H51C 109.5 . . ? H51A C51 H51C 109.5 . . ? H51B C51 H51C 109.5 . . ? O16 C52 C54 102.1(4) . . ? O16 C52 C55 109.9(5) . . ? C54 C52 C55 110.9(5) . . ? O16 C52 C53 110.0(4) . . ? C54 C52 C53 110.7(5) . . ? C55 C52 C53 112.8(5) . . ? C52 C53 H53A 109.5 . . ? C52 C53 H53B 109.5 . . ? H53A C53 H53B 109.5 . . ? C52 C53 H53C 109.5 . . ? H53A C53 H53C 109.5 . . ? H53B C53 H53C 109.5 . . ? C52 C54 H54A 109.5 . . ? C52 C54 H54B 109.5 . . ? H54A C54 H54B 109.5 . . ? C52 C54 H54C 109.5 . . ? H54A C54 H54C 109.5 . . ? H54B C54 H54C 109.5 . . ? C52 C55 H55A 109.5 . . ? C52 C55 H55B 109.5 . . ? H55A C55 H55B 109.5 . . ? C52 C55 H55C 109.5 . . ? H55A C55 H55C 109.5 . . ? H55B C55 H55C 109.5 . . ? O17 C56 N7 123.3(5) . . ? O17 C56 O16 124.5(5) . . ? N7 C56 O16 112.2(4) . . ? N7 C57 C59 111.3(4) . . ? N7 C57 C58 110.9(4) . . ? C59 C57 C58 109.7(4) . . ? N7 C57 H57 108.3 . . ? C59 C57 H57 108.3 . . ? C58 C57 H57 108.3 . . ? C57 C58 H58A 109.5 . . ? C57 C58 H58B 109.5 . . ? H58A C58 H58B 109.5 . . ? C57 C58 H58C 109.5 . . ? H58A C58 H58C 109.5 . . ? H58B C58 H58C 109.5 . . ? O18 C59 N8 123.7(4) . . ? O18 C59 C57 120.6(4) . . ? N8 C59 C57 115.7(4) . . ? N8 C60 C64 112.1(4) . . ? N8 C60 C61 111.2(4) . . ? C64 C60 C61 113.7(4) . . ? N8 C60 H60 106.4 . . ? C64 C60 H60 106.4 . . ? C61 C60 H60 106.4 . . ? C63 C61 C62 110.4(5) . . ? C63 C61 C60 110.7(5) . . ? C62 C61 C60 112.2(5) . . ? C63 C61 H61 107.8 . . ? C62 C61 H61 107.8 . . ? C60 C61 H61 107.8 . . ? C61 C62 H62A 109.5 . . ? C61 C62 H62B 109.5 . . ? H62A C62 H62B 109.5 . . ? C61 C62 H62C 109.5 . . ? H62A C62 H62C 109.5 . . ? H62B C62 H62C 109.5 . . ? C61 C63 H63A 109.5 . . ? C61 C63 H63B 109.5 . . ? H63A C63 H63B 109.5 . . ? C61 C63 H63C 109.5 . . ? H63A C63 H63C 109.5 . . ? H63B C63 H63C 109.5 . . ? C65 C64 C60 128.0(5) . . ? C65 C64 H64 116.0 . . ? C60 C64 H64 116.0 . . ? C64 C65 C66 123.6(6) . . ? C64 C65 H65 118.2 . . ? C66 C65 H65 118.2 . . ? O19 C66 O20 124.0(7) . . ? O19 C66 C65 123.9(6) . . ? O20 C66 C65 111.9(6) . . ? C68 C67 O20 109.4(7) . . ? C68 C67 H67A 109.8 . . ? O20 C67 H67A 109.8 . . ? C68 C67 H67B 109.8 . . ? O20 C67 H67B 109.8 . . ? H67A C67 H67B 108.2 . . ? C67 C68 H68A 109.5 . . ? C67 C68 H68B 109.5 . . ? H68A C68 H68B 109.5 . . ? C67 C68 H68C 109.5 . . ? H68A C68 H68C 109.5 . . ? H68B C68 H68C 109.5 . . ? O21 C69 C71 111.2(4) . . ? O21 C69 C70 102.2(4) . . ? C71 C69 C70 109.6(5) . . ? O21 C69 C72 109.6(5) . . ? C71 C69 C72 112.4(5) . . ? C70 C69 C72 111.5(5) . . ? C69 C70 H70A 109.5 . . ? C69 C70 H70B 109.5 . . ? H70A C70 H70B 109.5 . . ? C69 C70 H70C 109.5 . . ? H70A C70 H70C 109.5 . . ? H70B C70 H70C 109.5 . . ? C69 C71 H71A 109.5 . . ? C69 C71 H71B 109.5 . . ? H71A C71 H71B 109.5 . . ? C69 C71 H71C 109.5 . . ? H71A C71 H71C 109.5 . . ? H71B C71 H71C 109.5 . . ? C69 C72 H72A 109.5 . . ? C69 C72 H72B 109.5 . . ? H72A C72 H72B 109.5 . . ? C69 C72 H72C 109.5 . . ? H72A C72 H72C 109.5 . . ? H72B C72 H72C 109.5 . . ? O22 C73 N9 124.1(5) . . ? O22 C73 O21 123.4(5) . . ? N9 C73 O21 112.5(4) . . ? N9 C74 C75 110.5(4) . . ? N9 C74 C76 110.5(4) . . ? C75 C74 C76 108.6(4) . . ? N9 C74 H74 109.0 . . ? C75 C74 H74 109.0 . . ? C76 C74 H74 109.0 . . ? C74 C75 H75A 109.5 . . ? C74 C75 H75B 109.5 . . ? H75A C75 H75B 109.5 . . ? C74 C75 H75C 109.5 . . ? H75A C75 H75C 109.5 . . ? H75B C75 H75C 109.5 . . ? O23 C76 N10 124.5(4) . . ? O23 C76 C74 119.8(4) . . ? N10 C76 C74 115.7(4) . . ? N10 C77 C81 110.8(4) . . ? N10 C77 C78 112.2(4) . . ? C81 C77 C78 113.3(5) . . ? N10 C77 H77 106.7 . . ? C81 C77 H77 106.7 . . ? C78 C77 H77 106.7 . . ? C79 C78 C80 111.4(5) . . ? C79 C78 C77 111.1(5) . . ? C80 C78 C77 111.8(5) . . ? C79 C78 H78 107.4 . . ? C80 C78 H78 107.4 . . ? C77 C78 H78 107.4 . . ? C78 C79 H79A 109.5 . . ? C78 C79 H79B 109.5 . . ? H79A C79 H79B 109.5 . . ? C78 C79 H79C 109.5 . . ? H79A C79 H79C 109.5 . . ? H79B C79 H79C 109.5 . . ? C78 C80 H80A 109.5 . . ? C78 C80 H80B 109.5 . . ? H80A C80 H80B 109.5 . . ? C78 C80 H80C 109.5 . . ? H80A C80 H80C 109.5 . . ? H80B C80 H80C 109.5 . . ? C82 C81 C77 126.4(5) . . ? C82 C81 H81 116.8 . . ? C77 C81 H81 116.8 . . ? C81 C82 C83 124.6(5) . . ? C81 C82 H82 117.7 . . ? C83 C82 H82 117.7 . . ? O24 C83 O25 122.4(6) . . ? O24 C83 C82 125.3(5) . . ? O25 C83 C82 112.3(5) . . ? O25 C84 C85 109.0(6) . . ? O25 C84 H84A 109.9 . . ? C85 C84 H84A 109.9 . . ? O25 C84 H84B 109.9 . . ? C85 C84 H84B 109.9 . . ? H84A C84 H84B 108.3 . . ? C84 C85 H85A 109.5 . . ? C84 C85 H85B 109.5 . . ? H85A C85 H85B 109.5 . . ? C84 C85 H85C 109.5 . . ? H85A C85 H85C 109.5 . . ? H85B C85 H85C 109.5 . . ? O26 C86 C87 101.3(5) . . ? O26 C86 C89 111.1(5) . . ? C87 C86 C89 111.0(5) . . ? O26 C86 C88 110.1(5) . . ? C87 C86 C88 111.3(5) . . ? C89 C86 C88 111.6(5) . . ? C86 C87 H87A 109.5 . . ? C86 C87 H87B 109.5 . . ? H87A C87 H87B 109.5 . . ? C86 C87 H87C 109.5 . . ? H87A C87 H87C 109.5 . . ? H87B C87 H87C 109.5 . . ? C86 C88 H88A 109.5 . . ? C86 C88 H88B 109.5 . . ? H88A C88 H88B 109.5 . . ? C86 C88 H88C 109.5 . . ? H88A C88 H88C 109.5 . . ? H88B C88 H88C 109.5 . . ? C86 C89 H89A 109.5 . . ? C86 C89 H89B 109.5 . . ? H89A C89 H89B 109.5 . . ? C86 C89 H89C 109.5 . . ? H89A C89 H89C 109.5 . . ? H89B C89 H89C 109.5 . . ? O27 C90 N11 123.2(4) . . ? O27 C90 O26 125.4(5) . . ? N11 C90 O26 111.4(4) . . ? N11 C91 C92 111.5(4) . . ? N11 C91 C93 111.0(4) . . ? C92 C91 C93 109.1(4) . . ? N11 C91 H91 108.4 . . ? C92 C91 H91 108.4 . . ? C93 C91 H91 108.4 . . ? C91 C92 H92A 109.5 . . ? C91 C92 H92B 109.5 . . ? H92A C92 H92B 109.5 . . ? C91 C92 H92C 109.5 . . ? H92A C92 H92C 109.5 . . ? H92B C92 H92C 109.5 . . ? O28 C93 N12 124.7(4) . . ? O28 C93 C91 120.3(4) . . ? N12 C93 C91 114.9(4) . . ? N12 C94 C98 110.2(4) . . ? N12 C94 C95 111.4(4) . . ? C98 C94 C95 113.8(4) . . ? N12 C94 H94 107.0 . . ? C98 C94 H94 107.0 . . ? C95 C94 H94 107.0 . . ? C96 C95 C94 111.4(4) . . ? C96 C95 C97 109.7(5) . . ? C94 C95 C97 113.0(5) . . ? C96 C95 H95 107.5 . . ? C94 C95 H95 107.5 . . ? C97 C95 H95 107.5 . . ? C95 C96 H96A 109.5 . . ? C95 C96 H96B 109.5 . . ? H96A C96 H96B 109.5 . . ? C95 C96 H96C 109.5 . . ? H96A C96 H96C 109.5 . . ? H96B C96 H96C 109.5 . . ? C95 C97 H97A 109.5 . . ? C95 C97 H97B 109.5 . . ? H97A C97 H97B 109.5 . . ? C95 C97 H97C 109.5 . . ? H97A C97 H97C 109.5 . . ? H97B C97 H97C 109.5 . . ? C99 C98 C94 127.7(5) . . ? C99 C98 H98 116.1 . . ? C94 C98 H98 116.1 . . ? C98 C99 C100 122.8(5) . . ? C98 C99 H99 118.6 . . ? C100 C99 H99 118.6 . . ? O29 C100 O30 123.9(5) . . ? O29 C100 C99 124.7(6) . . ? O30 C100 C99 111.3(5) . . ? O30 C101 C102 110.6(6) . . ? O30 C101 H10B 109.5 . . ? C102 C101 H10B 109.5 . . ? O30 C101 H10C 109.5 . . ? C102 C101 H10C 109.5 . . ? H10B C101 H10C 108.1 . . ? C101 C102 H10D 109.5 . . ? C101 C102 H10E 109.5 . . ? H10D C102 H10E 109.5 . . ? C101 C102 H10F 109.5 . . ? H10D C102 H10F 109.5 . . ? H10E C102 H10F 109.5 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.587 _refine_diff_density_min -0.334 _refine_diff_density_rms 0.084 # Attachment 'Boc-dgAib.cif' data_mo_anu_aibdg_1_0m _database_code_depnum_ccdc_archive 'CCDC 825101' #TrackingRef 'Boc-dgAib.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic '(E)-ethyl 4-(tert-butoxycarbonylamino)-4-methylpent-2-enoate' _chemical_name_common Boc-dgAib-OEt _chemical_formula_moiety 'C13 H24 N O4' _chemical_formula_sum 'C13 H24 N O4' _chemical_compound_source Synthesis _exptl_crystal_recrystallization_method MeOH _chemical_melting_point ? _exptl_crystal_description Rectangular _exptl_crystal_colour Colorless _diffrn_ambient_temperature 296(2) _diffrn_ambient_pressure 101.325 _chemical_formula_weight 258.33 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 monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_int_tables_number 14 _chemical_absolute_configuration syn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.669(2) _cell_length_b 9.092(2) _cell_length_c 15.882(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.923(5) _cell_angle_gamma 90.00 _cell_volume 1540.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1853 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 21.06 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.114 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 564 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.970 _exptl_absorpt_correction_T_max 0.982 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Graphite monochromator' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 16600 _diffrn_reflns_av_R_equivalents 0.0579 _diffrn_reflns_av_sigmaI/netI 0.0563 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 30.28 _reflns_number_total 4448 _reflns_number_gt 1713 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1201P)^2^+0.0056P] 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 4448 _refine_ls_number_parameters 169 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1649 _refine_ls_R_factor_gt 0.0651 _refine_ls_wR_factor_ref 0.2427 _refine_ls_wR_factor_gt 0.1879 _refine_ls_goodness_of_fit_ref 0.986 _refine_ls_restrained_S_all 1.031 _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 -0.2593(2) 0.6560(3) 0.95965(13) 0.1027(7) Uani 1 1 d . . . O2 O -0.2944(2) 0.5430(3) 0.83821(14) 0.1103(8) Uani 1 1 d . . . O3 O 0.14799(18) 0.74120(19) 0.83030(11) 0.0784(6) Uani 1 1 d . . . O4 O 0.26227(16) 0.69316(18) 0.94912(11) 0.0729(6) Uani 1 1 d . . . N1 N 0.17749(18) 0.5081(2) 0.87952(12) 0.0619(6) Uani 1 1 d . . . H1 H 0.2191 0.4569 0.9159 0.074 Uiso 1 1 calc R . . C1 C 0.1466(3) 0.9118(4) 0.9930(2) 0.0972(10) Uani 1 1 d . . . H1A H 0.1568 1.0098 1.0144 0.146 Uiso 1 1 calc R . . H1B H 0.1046 0.8525 1.0339 0.146 Uiso 1 1 calc R . . H1C H 0.0977 0.9144 0.9418 0.146 Uiso 1 1 calc R . . C2 C 0.2739(2) 0.8464(3) 0.97565(17) 0.0717(7) Uani 1 1 d . . . C3 C 0.3423(3) 0.9355(4) 0.9106(2) 0.1027(11) Uani 1 1 d . . . H3A H 0.4248 0.8958 0.9035 0.154 Uiso 1 1 calc R . . H3B H 0.3486 1.0358 0.9291 0.154 Uiso 1 1 calc R . . H3C H 0.2970 0.9315 0.8580 0.154 Uiso 1 1 calc R . . C4 C 0.3499(4) 0.8353(4) 1.0572(2) 0.1100(12) Uani 1 1 d . . . H4A H 0.4295 0.7906 1.0462 0.165 Uiso 1 1 calc R . . H4B H 0.3052 0.7764 1.0969 0.165 Uiso 1 1 calc R . . H4C H 0.3630 0.9320 1.0800 0.165 Uiso 1 1 calc R . . C5 C 0.1915(2) 0.6553(3) 0.88119(15) 0.0597(6) Uani 1 1 d . . . C6 C 0.0956(2) 0.4293(2) 0.81939(14) 0.0594(6) Uani 1 1 d . . . C7 C 0.1358(3) 0.4554(3) 0.72846(16) 0.0796(8) Uani 1 1 d . . . H7A H 0.2212 0.4247 0.7222 0.119 Uiso 1 1 calc R . . H7B H 0.1286 0.5582 0.7153 0.119 Uiso 1 1 calc R . . H7C H 0.0827 0.3998 0.6909 0.119 Uiso 1 1 calc R . . C8 C 0.1098(3) 0.2660(3) 0.83960(19) 0.0812(8) Uani 1 1 d . . . H8A H 0.0917 0.2495 0.8979 0.122 Uiso 1 1 calc R . . H8B H 0.1941 0.2354 0.8286 0.122 Uiso 1 1 calc R . . H8C H 0.0525 0.2102 0.8050 0.122 Uiso 1 1 calc R . . C9 C -0.0406(2) 0.4709(3) 0.82933(16) 0.0629(6) Uani 1 1 d . . . H9 H -0.0961 0.4380 0.7876 0.075 Uiso 1 1 calc R . . C10 C -0.0894(2) 0.5489(3) 0.89081(15) 0.0661(7) Uani 1 1 d . . . H10 H -0.0340 0.5825 0.9323 0.079 Uiso 1 1 calc R . . C11 C -0.2198(3) 0.5875(3) 0.90035(18) 0.0750(8) Uani 1 1 d . . . C12 C -0.4292(4) 0.5756(8) 0.8491(3) 0.186(3) Uani 1 1 d D . . H12A H -0.4690 0.4926 0.8763 0.223 Uiso 1 1 calc R . . H12B H -0.4377 0.6605 0.8856 0.223 Uiso 1 1 calc R . . C13 C -0.4862(5) 0.6018(12) 0.7775(4) 0.271(5) Uani 1 1 d D . . H13A H -0.4329 0.6598 0.7425 0.407 Uiso 1 1 calc R . . H13B H -0.5626 0.6544 0.7874 0.407 Uiso 1 1 calc R . . H13C H -0.5051 0.5104 0.7498 0.407 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 0.1031(17) 0.1243(18) 0.0810(14) 0.0016(13) 0.0107(12) 0.0377(13) O2 0.0672(14) 0.173(2) 0.0907(16) -0.0139(14) -0.0107(11) 0.0194(13) O3 0.0952(15) 0.0637(11) 0.0758(12) 0.0120(9) -0.0164(10) -0.0070(9) O4 0.0757(12) 0.0643(11) 0.0779(11) -0.0014(8) -0.0196(9) -0.0078(8) N1 0.0681(13) 0.0561(12) 0.0611(12) 0.0051(9) -0.0090(10) -0.0017(9) C1 0.077(2) 0.108(2) 0.108(2) -0.0226(19) 0.0187(17) 0.0014(17) C2 0.0670(17) 0.0645(15) 0.0835(17) -0.0093(13) 0.0007(13) -0.0156(12) C3 0.095(2) 0.088(2) 0.126(3) -0.0115(19) 0.027(2) -0.0324(17) C4 0.109(3) 0.112(3) 0.108(3) -0.022(2) -0.034(2) -0.019(2) C5 0.0626(15) 0.0582(14) 0.0581(14) 0.0034(11) -0.0029(11) -0.0046(11) C6 0.0646(16) 0.0583(14) 0.0553(13) -0.0033(10) -0.0033(11) -0.0046(11) C7 0.082(2) 0.0944(19) 0.0627(16) -0.0075(14) 0.0052(13) -0.0022(15) C8 0.095(2) 0.0570(15) 0.0913(19) -0.0066(13) -0.0014(15) -0.0023(14) C9 0.0669(16) 0.0655(14) 0.0562(14) 0.0010(11) -0.0044(11) -0.0065(12) C10 0.0680(17) 0.0731(15) 0.0570(14) 0.0011(12) -0.0065(12) 0.0007(13) C11 0.0741(19) 0.090(2) 0.0607(16) 0.0090(14) 0.0006(14) 0.0138(15) C12 0.088(3) 0.338(8) 0.132(4) -0.008(4) -0.016(3) 0.082(4) C13 0.104(4) 0.561(16) 0.148(5) -0.063(7) -0.003(4) 0.111(6) _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 C11 1.211(3) . ? O2 C11 1.321(3) . ? O2 C12 1.482(5) . ? O3 C5 1.211(3) . ? O4 C5 1.351(3) . ? O4 C2 1.460(3) . ? N1 C5 1.347(3) . ? N1 C6 1.470(3) . ? C1 C2 1.512(4) . ? C2 C3 1.510(4) . ? C2 C4 1.520(4) . ? C6 C9 1.513(3) . ? C6 C8 1.527(3) . ? C6 C7 1.531(4) . ? C9 C10 1.320(3) . ? C10 C11 1.445(4) . ? C12 C13 1.303(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 O2 C12 115.2(3) . . ? C5 O4 C2 121.14(19) . . ? C5 N1 C6 124.15(19) . . ? O4 C2 C3 110.7(2) . . ? O4 C2 C1 110.8(2) . . ? C3 C2 C1 111.1(3) . . ? O4 C2 C4 103.0(2) . . ? C3 C2 C4 111.2(3) . . ? C1 C2 C4 109.8(3) . . ? O3 C5 N1 125.9(2) . . ? O3 C5 O4 124.9(2) . . ? N1 C5 O4 109.21(19) . . ? N1 C6 C9 111.86(19) . . ? N1 C6 C8 106.3(2) . . ? C9 C6 C8 108.3(2) . . ? N1 C6 C7 111.4(2) . . ? C9 C6 C7 110.1(2) . . ? C8 C6 C7 108.7(2) . . ? C10 C9 C6 127.0(2) . . ? C9 C10 C11 126.8(2) . . ? O1 C11 O2 121.7(3) . . ? O1 C11 C10 123.7(3) . . ? O2 C11 C10 114.6(2) . . ? C13 C12 O2 112.0(4) . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 30.28 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.303 _refine_diff_density_min -0.283 _refine_diff_density_rms 0.037 # Attachment 'Boc-dgIle.cif' data_mgk _database_code_depnum_ccdc_archive 'CCDC 825102' #TrackingRef 'Boc-dgIle.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic '(4S,5S,E)-ethyl 4-(tert-butoxycarbonylamino)-5-methylhept-2-enoate' _chemical_name_common Boc-dgI-OEt _chemical_formula_moiety 'C15 H27 N O4' _chemical_formula_sum 'C15 H27 N O4' _chemical_compound_source Synthesis _exptl_crystal_recrystallization_method EtOAc/Hexane _chemical_melting_point ? _exptl_crystal_description 'Rectangular block' _exptl_crystal_colour Colorless _diffrn_ambient_temperature 200(2) _diffrn_ambient_pressure 101.325 _chemical_formula_weight 285.38 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 orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_int_tables_number 19 _chemical_absolute_configuration syn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 10.153(3) _cell_length_b 10.273(3) _cell_length_c 16.191(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1688.8(9) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.122 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.961 _exptl_absorpt_correction_T_max 0.975 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Graphite monochromator' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 30707 _diffrn_reflns_av_R_equivalents 0.0265 _diffrn_reflns_av_sigmaI/netI 0.0166 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 28.60 _reflns_number_total 4302 _reflns_number_gt 3750 _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^)+(0.0460P)^2^+0.2308P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.6(9) _refine_ls_number_reflns 4302 _refine_ls_number_parameters 188 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0455 _refine_ls_R_factor_gt 0.0378 _refine_ls_wR_factor_ref 0.0961 _refine_ls_wR_factor_gt 0.0912 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 C1 C 0.27512(16) 0.49741(13) 0.22488(11) 0.0525(4) Uani 1 1 d . . . H1A H 0.2009 0.5047 0.2613 0.079 Uiso 1 1 calc R . . H1B H 0.3306 0.4273 0.2429 0.079 Uiso 1 1 calc R . . H1C H 0.2448 0.4804 0.1698 0.079 Uiso 1 1 calc R . . C2 C 0.39333(17) 0.65858(16) 0.31258(9) 0.0519(4) Uani 1 1 d . . . H2A H 0.4429 0.7381 0.3118 0.078 Uiso 1 1 calc R . . H2B H 0.4467 0.5900 0.3350 0.078 Uiso 1 1 calc R . . H2C H 0.3162 0.6698 0.3462 0.078 Uiso 1 1 calc R . . C3 C 0.46893(15) 0.61572(14) 0.16819(9) 0.0478(3) Uani 1 1 d . . . H3A H 0.4382 0.6023 0.1128 0.072 Uiso 1 1 calc R . . H3B H 0.5244 0.5443 0.1842 0.072 Uiso 1 1 calc R . . H3C H 0.5182 0.6954 0.1708 0.072 Uiso 1 1 calc R . . C4 C 0.35277(13) 0.62377(12) 0.22598(8) 0.0380(3) Uani 1 1 d . . . C5 C 0.29026(12) 0.84539(11) 0.18790(8) 0.0339(2) Uani 1 1 d . . . C6 C 0.19671(13) 1.05684(11) 0.15448(9) 0.0381(3) Uani 1 1 d . . . H6 H 0.2907 1.0777 0.1504 0.046 Uiso 1 1 calc R . . C7 C 0.13166(13) 1.10986(12) 0.07587(9) 0.0411(3) Uani 1 1 d . . . H7 H 0.1538 1.2026 0.0726 0.049 Uiso 1 1 calc R . . C8 C 0.18915(18) 1.04569(16) -0.00010(10) 0.0547(4) Uani 1 1 d . . . H8A H 0.2836 1.0485 0.0027 0.082 Uiso 1 1 calc R . . H8B H 0.1599 1.0911 -0.0486 0.082 Uiso 1 1 calc R . . H8C H 0.1605 0.9567 -0.0027 0.082 Uiso 1 1 calc R . . C9 C -0.01792(14) 1.10062(15) 0.07761(10) 0.0487(3) Uani 1 1 d . . . H9A H -0.0434 1.0098 0.0736 0.058 Uiso 1 1 calc R . . H9B H -0.0495 1.1334 0.1302 0.058 Uiso 1 1 calc R . . C10 C 0.14649(13) 1.12448(12) 0.22992(9) 0.0409(3) Uani 1 1 d . . . H10 H 0.1493 1.2150 0.2296 0.049 Uiso 1 1 calc R . . C11 C 0.09900(14) 1.06918(13) 0.29631(9) 0.0423(3) Uani 1 1 d . . . H11 H 0.0940 0.9789 0.2989 0.051 Uiso 1 1 calc R . . C12 C 0.05335(14) 1.14716(15) 0.36688(10) 0.0471(3) Uani 1 1 d . . . C26 C -0.08346(18) 1.17589(17) 0.00871(12) 0.0627(5) Uani 1 1 d . . . H26A H -0.0545 1.2648 0.0102 0.094 Uiso 1 1 calc R . . H26B H -0.1773 1.1728 0.0156 0.094 Uiso 1 1 calc R . . H26C H -0.0602 1.1379 -0.0435 0.094 Uiso 1 1 calc R . . C30 C -0.0293(2) 1.1338(2) 0.50397(12) 0.0778(6) Uani 1 1 d . . . H30A H 0.0129 1.0909 0.5503 0.093 Uiso 1 1 calc R . . H30B H -0.0009 1.2239 0.5034 0.093 Uiso 1 1 calc R . . C31 C -0.1692(2) 1.1287(3) 0.51436(13) 0.0852(7) Uani 1 1 d . . . H31A H -0.2111 1.1751 0.4701 0.128 Uiso 1 1 calc R . . H31B H -0.1927 1.1679 0.5661 0.128 Uiso 1 1 calc R . . H31C H -0.1978 1.0396 0.5138 0.128 Uiso 1 1 calc R . . N2 N 0.18751(10) 0.91597(9) 0.16081(7) 0.0368(2) Uani 1 1 d . . . H2 H 0.1156 0.8774 0.1471 0.044 Uiso 1 1 d R . . O1 O 0.25545(9) 0.71940(8) 0.19546(6) 0.0381(2) Uani 1 1 d . . . O2 O 0.39821(9) 0.88964(9) 0.20223(7) 0.0474(2) Uani 1 1 d . . . O3 O 0.05497(11) 1.26476(10) 0.36965(8) 0.0594(3) Uani 1 1 d . . . O4 O 0.01107(12) 1.07091(12) 0.42757(7) 0.0606(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0564(9) 0.0355(7) 0.0656(10) 0.0072(6) -0.0021(7) 0.0036(6) C2 0.0561(9) 0.0598(9) 0.0397(7) 0.0027(6) -0.0058(6) 0.0111(7) C3 0.0493(8) 0.0461(7) 0.0479(8) 0.0052(6) 0.0051(6) 0.0139(6) C4 0.0389(7) 0.0345(6) 0.0406(7) 0.0035(5) -0.0032(5) 0.0086(5) C5 0.0336(6) 0.0309(5) 0.0372(6) -0.0035(5) -0.0036(5) 0.0001(5) C6 0.0318(6) 0.0268(5) 0.0557(8) 0.0013(5) -0.0052(6) -0.0022(5) C7 0.0397(7) 0.0324(6) 0.0512(7) 0.0058(5) 0.0011(6) -0.0029(5) C8 0.0569(10) 0.0498(8) 0.0573(9) 0.0004(7) 0.0063(8) 0.0000(7) C9 0.0401(7) 0.0505(8) 0.0554(8) 0.0151(7) -0.0040(6) 0.0024(6) C10 0.0370(7) 0.0285(5) 0.0573(8) -0.0044(5) -0.0116(6) 0.0022(5) C11 0.0413(7) 0.0329(6) 0.0527(8) -0.0057(6) -0.0094(6) 0.0058(5) C12 0.0347(7) 0.0504(8) 0.0562(8) -0.0150(7) -0.0152(6) 0.0111(6) C26 0.0574(10) 0.0617(10) 0.0690(11) 0.0180(8) -0.0092(8) 0.0135(8) C30 0.0703(12) 0.1055(16) 0.0575(10) -0.0291(11) 0.0019(9) 0.0078(11) C31 0.0682(13) 0.128(2) 0.0596(11) -0.0118(12) 0.0084(9) -0.0061(13) N2 0.0293(5) 0.0274(5) 0.0536(6) -0.0018(4) -0.0063(5) -0.0011(4) O1 0.0355(4) 0.0289(4) 0.0498(5) 0.0010(4) -0.0083(4) 0.0025(3) O2 0.0352(5) 0.0390(5) 0.0680(7) -0.0001(4) -0.0143(5) -0.0020(4) O3 0.0512(6) 0.0472(6) 0.0800(8) -0.0241(5) -0.0161(6) 0.0124(5) O4 0.0628(7) 0.0679(7) 0.0511(6) -0.0122(6) 0.0021(6) 0.0084(6) _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 C1 C4 1.519(2) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C4 1.504(2) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 C4 1.508(2) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 O1 1.4784(15) . ? C5 O2 1.2090(15) . ? C5 N2 1.3440(16) . ? C5 O1 1.3473(15) . ? C6 N2 1.4538(15) . ? C6 C10 1.495(2) . ? C6 C7 1.534(2) . ? C6 H6 0.9800 . ? C7 C8 1.513(2) . ? C7 C9 1.522(2) . ? C7 H7 0.9800 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C26 1.512(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.308(2) . ? C10 H10 0.9300 . ? C11 C12 1.470(2) . ? C11 H11 0.9300 . ? C12 O3 1.2091(18) . ? C12 O4 1.328(2) . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C30 C31 1.431(3) . ? C30 O4 1.454(2) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? N2 H2 0.8600 . ? 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 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 . . ? O1 C4 C2 109.66(11) . . ? O1 C4 C3 110.60(10) . . ? C2 C4 C3 112.17(13) . . ? O1 C4 C1 102.54(11) . . ? C2 C4 C1 110.86(12) . . ? C3 C4 C1 110.60(12) . . ? O2 C5 N2 124.30(11) . . ? O2 C5 O1 125.56(11) . . ? N2 C5 O1 110.14(10) . . ? N2 C6 C10 112.54(12) . . ? N2 C6 C7 112.60(11) . . ? C10 C6 C7 111.47(11) . . ? N2 C6 H6 106.6 . . ? C10 C6 H6 106.6 . . ? C7 C6 H6 106.6 . . ? C8 C7 C9 111.90(13) . . ? C8 C7 C6 110.72(12) . . ? C9 C7 C6 113.09(12) . . ? C8 C7 H7 106.9 . . ? C9 C7 H7 106.9 . . ? C6 C7 H7 106.9 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C26 C9 C7 113.18(13) . . ? C26 C9 H9A 108.9 . . ? C7 C9 H9A 108.9 . . ? C26 C9 H9B 108.9 . . ? C7 C9 H9B 108.9 . . ? H9A C9 H9B 107.8 . . ? C11 C10 C6 126.53(11) . . ? C11 C10 H10 116.7 . . ? C6 C10 H10 116.7 . . ? C10 C11 C12 121.21(13) . . ? C10 C11 H11 119.4 . . ? C12 C11 H11 119.4 . . ? O3 C12 O4 124.50(15) . . ? O3 C12 C11 124.68(16) . . ? O4 C12 C11 110.82(13) . . ? C9 C26 H26A 109.5 . . ? C9 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C9 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C31 C30 O4 111.33(18) . . ? C31 C30 H30A 109.4 . . ? O4 C30 H30A 109.4 . . ? C31 C30 H30B 109.4 . . ? O4 C30 H30B 109.4 . . ? H30A C30 H30B 108.0 . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C5 N2 C6 120.67(11) . . ? C5 N2 H2 119.6 . . ? C6 N2 H2 119.7 . . ? C5 O1 C4 119.57(10) . . ? C12 O4 C30 117.30(15) . . ? 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 N2 C6 C7 C8 -55.61(15) . . . . ? C10 C6 C7 C8 176.81(12) . . . . ? N2 C6 C7 C9 70.88(16) . . . . ? C10 C6 C7 C9 -56.70(15) . . . . ? C8 C7 C9 C26 -65.47(17) . . . . ? C6 C7 C9 C26 168.67(13) . . . . ? N2 C6 C10 C11 0.30(19) . . . . ? C7 C6 C10 C11 127.92(14) . . . . ? C6 C10 C11 C12 179.62(12) . . . . ? C10 C11 C12 O3 0.3(2) . . . . ? C10 C11 C12 O4 -179.12(13) . . . . ? O2 C5 N2 C6 -6.2(2) . . . . ? O1 C5 N2 C6 174.60(12) . . . . ? C10 C6 N2 C5 -93.85(15) . . . . ? C7 C6 N2 C5 139.13(12) . . . . ? O2 C5 O1 C4 1.93(19) . . . . ? N2 C5 O1 C4 -178.88(10) . . . . ? C2 C4 O1 C5 62.24(15) . . . . ? C3 C4 O1 C5 -61.98(15) . . . . ? C1 C4 O1 C5 -179.93(12) . . . . ? O3 C12 O4 C30 -3.4(2) . . . . ? C11 C12 O4 C30 176.07(14) . . . . ? C31 C30 O4 C12 108.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.60 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.185 _refine_diff_density_min -0.190 _refine_diff_density_rms 0.030 # Attachment 'Boc-dgL-dgl-OEt.cif' data_mo_sm_dgldi_0m _database_code_depnum_ccdc_archive 'CCDC 825103' #TrackingRef 'Boc-dgL-dgl-OEt.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C23 H40 N2 O5' _chemical_formula_sum 'C23 H40 N2 O5' _chemical_compound_source Synthesis _exptl_crystal_recrystallization_method EtOAc _chemical_melting_point ? _exptl_crystal_description 'Rectangular block' _exptl_crystal_colour Colorless _diffrn_ambient_temperature 100(2) _diffrn_ambient_pressure 101.325 _chemical_formula_weight 424.57 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 triclinic _symmetry_space_group_name_H-M 'P 1' _symmetry_int_tables_number 1 _chemical_absolute_configuration syn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 5.053(2) _cell_length_b 9.812(5) _cell_length_c 13.498(6) _cell_angle_alpha 73.640(9) _cell_angle_beta 84.653(9) _cell_angle_gamma 78.566(9) _cell_volume 628.8(5) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.121 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 232 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.976 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Graphite monchromator' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11459 _diffrn_reflns_av_R_equivalents 0.0613 _diffrn_reflns_av_sigmaI/netI 0.0936 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 29.13 _reflns_number_total 5271 _reflns_number_gt 3557 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0800P)^2^+0.0635P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1.8(15) _refine_ls_number_reflns 5271 _refine_ls_number_parameters 279 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1066 _refine_ls_R_factor_gt 0.0663 _refine_ls_wR_factor_ref 0.1751 _refine_ls_wR_factor_gt 0.1509 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.002 _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 0.0387(4) 0.6464(2) 0.33627(18) 0.0305(6) Uani 1 1 d . . . O2 O -0.2078(4) 0.4762(2) 0.33104(19) 0.0327(6) Uani 1 1 d . . . O3 O 0.6435(4) -0.0169(2) 0.59298(17) 0.0277(5) Uani 1 1 d . . . O4 O 0.0490(9) -0.5851(4) 0.8331(3) 0.0779(12) Uani 1 1 d . . . O5 O -0.1553(6) -0.5235(3) 0.6829(2) 0.0445(7) Uani 1 1 d . . . N1 N 0.2510(5) 0.4350(3) 0.3174(2) 0.0263(6) Uani 1 1 d . . . H1 H 0.3923 0.4734 0.3122 0.032 Uiso 1 1 calc R . . N2 N 0.2312(5) -0.0787(3) 0.64294(19) 0.0262(6) Uani 1 1 d . . . H2 H 0.0692 -0.0716 0.6249 0.031 Uiso 1 1 calc R . . C1 C -0.2002(6) 0.7560(3) 0.3456(3) 0.0285(7) Uani 1 1 d . . . C2 C -0.3691(7) 0.7022(4) 0.4428(3) 0.0343(8) Uani 1 1 d . . . H2A H -0.4767 0.6383 0.4309 0.051 Uiso 1 1 calc R . . H2B H -0.4854 0.7829 0.4601 0.051 Uiso 1 1 calc R . . H2C H -0.2521 0.6514 0.4986 0.051 Uiso 1 1 calc R . . C3 C -0.0725(7) 0.8790(4) 0.3567(3) 0.0401(9) Uani 1 1 d . . . H3A H 0.0421 0.8446 0.4148 0.060 Uiso 1 1 calc R . . H3B H -0.2120 0.9561 0.3673 0.060 Uiso 1 1 calc R . . H3C H 0.0329 0.9136 0.2951 0.060 Uiso 1 1 calc R . . C4 C -0.3567(7) 0.8031(4) 0.2478(3) 0.0310(8) Uani 1 1 d . . . H4A H -0.2345 0.8240 0.1889 0.047 Uiso 1 1 calc R . . H4B H -0.4884 0.8882 0.2483 0.047 Uiso 1 1 calc R . . H4C H -0.4463 0.7272 0.2441 0.047 Uiso 1 1 calc R . . C5 C 0.0108(7) 0.5141(3) 0.3287(3) 0.0278(7) Uani 1 1 d . . . C6 C 0.2855(6) 0.2852(3) 0.3134(2) 0.0244(7) Uani 1 1 d . . . H6 H 0.1072 0.2638 0.3072 0.029 Uiso 1 1 calc R . . C7 C 0.4641(7) 0.2607(3) 0.2196(2) 0.0278(7) Uani 1 1 d . . . H7A H 0.5463 0.1594 0.2344 0.033 Uiso 1 1 calc R . . H7B H 0.6086 0.3157 0.2101 0.033 Uiso 1 1 calc R . . C8 C 0.3159(11) 0.3029(5) 0.1184(3) 0.0609(13) Uani 1 1 d . . . H8 H 0.1850 0.2383 0.1276 0.073 Uiso 1 1 calc R . . C9 C 0.1687(14) 0.4470(6) 0.0867(4) 0.0835(19) Uani 1 1 d . . . H9A H 0.0392 0.4647 0.1404 0.125 Uiso 1 1 calc R . . H9B H 0.0763 0.4594 0.0249 0.125 Uiso 1 1 calc R . . H9C H 0.2915 0.5138 0.0735 0.125 Uiso 1 1 calc R . . C10 C 0.5270(13) 0.2678(6) 0.0331(3) 0.0787(18) Uani 1 1 d . . . H10A H 0.4355 0.2775 -0.0284 0.118 Uiso 1 1 calc R . . H10B H 0.6234 0.1707 0.0570 0.118 Uiso 1 1 calc R . . H10C H 0.6520 0.3337 0.0182 0.118 Uiso 1 1 calc R . . C11 C 0.4015(6) 0.1873(3) 0.4120(2) 0.0233(6) Uani 1 1 d . . . H11 H 0.5740 0.1938 0.4268 0.028 Uiso 1 1 calc R . . C12 C 0.2751(6) 0.0914(3) 0.4804(2) 0.0234(6) Uani 1 1 d . . . H12 H 0.1011 0.0845 0.4677 0.028 Uiso 1 1 calc R . . C13 C 0.4031(6) -0.0041(3) 0.5757(2) 0.0231(6) Uani 1 1 d . . . C14 C 0.3122(7) -0.1704(4) 0.7447(2) 0.0282(7) Uani 1 1 d . . . H14 H 0.5101 -0.1926 0.7432 0.034 Uiso 1 1 calc R . . C15 C 0.2202(7) -0.0836(4) 0.8247(3) 0.0327(8) Uani 1 1 d . . . H15A H 0.3082 0.0000 0.8058 0.039 Uiso 1 1 calc R . . H15B H 0.0274 -0.0481 0.8190 0.039 Uiso 1 1 calc R . . C16 C 0.2743(7) -0.1622(4) 0.9384(3) 0.0361(9) Uani 1 1 d . . . H16 H 0.1687 -0.2401 0.9597 0.043 Uiso 1 1 calc R . . C17 C 0.1783(10) -0.0588(6) 1.0052(3) 0.0556(12) Uani 1 1 d . . . H17A H 0.1967 -0.1107 1.0767 0.083 Uiso 1 1 calc R . . H17B H -0.0080 -0.0163 0.9928 0.083 Uiso 1 1 calc R . . H17C H 0.2855 0.0158 0.9881 0.083 Uiso 1 1 calc R . . C18 C 0.5719(8) -0.2297(5) 0.9547(3) 0.0507(12) Uani 1 1 d . . . H18A H 0.6804 -0.1560 0.9307 0.076 Uiso 1 1 calc R . . H18B H 0.6240 -0.3008 0.9167 0.076 Uiso 1 1 calc R . . H18C H 0.5984 -0.2749 1.0269 0.076 Uiso 1 1 calc R . . C19 C 0.2133(7) -0.3107(4) 0.7712(3) 0.0339(8) Uani 1 1 d . . . H19 H 0.2591 -0.3738 0.8354 0.041 Uiso 1 1 calc R . . C20 C 0.0678(7) -0.3557(4) 0.7140(3) 0.0340(8) Uani 1 1 d . . . H20 H 0.0138 -0.2965 0.6495 0.041 Uiso 1 1 calc R . . C21 C -0.0080(9) -0.4993(4) 0.7524(3) 0.0426(10) Uani 1 1 d . . . C22 C -0.2461(11) -0.6628(4) 0.7115(3) 0.0528(12) Uani 1 1 d . . . H22A H -0.3669 -0.6706 0.7723 0.063 Uiso 1 1 calc R . . H22B H -0.0926 -0.7413 0.7268 0.063 Uiso 1 1 calc R . . C23 C -0.3899(13) -0.6702(5) 0.6219(4) 0.0653(15) Uani 1 1 d . . . H23A H -0.5325 -0.5878 0.6040 0.098 Uiso 1 1 calc R . . H23B H -0.4651 -0.7569 0.6402 0.098 Uiso 1 1 calc R . . H23C H -0.2647 -0.6705 0.5639 0.098 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 0.0197(12) 0.0203(11) 0.0591(17) -0.0206(11) -0.0055(10) -0.0049(9) O2 0.0223(12) 0.0318(13) 0.0518(15) -0.0180(11) -0.0044(10) -0.0121(10) O3 0.0241(12) 0.0293(12) 0.0336(13) -0.0077(10) -0.0042(9) -0.0135(9) O4 0.137(3) 0.054(2) 0.0499(18) 0.0152(15) -0.0461(19) -0.057(2) O5 0.0711(19) 0.0289(13) 0.0405(15) -0.0063(11) -0.0176(13) -0.0225(13) N1 0.0208(14) 0.0188(13) 0.0434(16) -0.0102(12) -0.0031(11) -0.0097(10) N2 0.0261(14) 0.0330(15) 0.0238(14) -0.0077(11) -0.0031(10) -0.0140(12) C1 0.0246(17) 0.0225(17) 0.044(2) -0.0142(15) -0.0056(14) -0.0082(13) C2 0.0314(19) 0.038(2) 0.039(2) -0.0167(16) -0.0067(14) -0.0068(15) C3 0.0256(19) 0.032(2) 0.074(3) -0.0308(19) -0.0064(17) -0.0055(15) C4 0.0285(18) 0.0280(18) 0.038(2) -0.0086(14) -0.0011(14) -0.0079(14) C5 0.0290(17) 0.0251(17) 0.0354(18) -0.0106(14) -0.0066(13) -0.0132(14) C6 0.0296(17) 0.0147(14) 0.0324(17) -0.0074(13) -0.0058(13) -0.0089(12) C7 0.0360(19) 0.0210(17) 0.0286(17) -0.0074(13) -0.0030(14) -0.0086(14) C8 0.082(4) 0.060(3) 0.039(2) -0.019(2) -0.014(2) 0.005(3) C9 0.106(5) 0.094(5) 0.040(3) -0.013(3) -0.016(3) 0.005(4) C10 0.116(5) 0.081(4) 0.032(2) -0.026(2) -0.010(3) 0.019(3) C11 0.0222(15) 0.0218(16) 0.0310(17) -0.0124(13) -0.0048(12) -0.0064(12) C12 0.0205(15) 0.0243(16) 0.0306(17) -0.0119(13) -0.0010(12) -0.0092(12) C13 0.0256(17) 0.0254(16) 0.0225(15) -0.0108(13) -0.0024(12) -0.0073(13) C14 0.0257(17) 0.0323(18) 0.0299(18) -0.0068(14) -0.0054(13) -0.0133(14) C15 0.0331(19) 0.039(2) 0.0318(18) -0.0088(15) -0.0023(14) -0.0199(16) C16 0.0291(19) 0.056(2) 0.0317(19) -0.0145(17) -0.0031(14) -0.0236(17) C17 0.057(3) 0.083(3) 0.042(2) -0.033(2) 0.006(2) -0.028(2) C18 0.037(2) 0.088(4) 0.033(2) -0.016(2) -0.0038(16) -0.022(2) C19 0.042(2) 0.0328(19) 0.0272(18) -0.0023(15) -0.0064(14) -0.0137(16) C20 0.039(2) 0.0323(19) 0.0317(18) -0.0053(15) -0.0077(14) -0.0112(15) C21 0.063(3) 0.036(2) 0.033(2) -0.0031(17) -0.0134(18) -0.0221(19) C22 0.086(3) 0.030(2) 0.048(2) -0.0050(18) -0.015(2) -0.025(2) C23 0.111(4) 0.047(3) 0.056(3) -0.020(2) -0.010(3) -0.045(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 O1 C5 1.365(4) . ? O1 C1 1.471(4) . ? O2 C5 1.228(4) . ? O3 C13 1.233(4) . ? O4 C21 1.194(5) . ? O5 C21 1.347(5) . ? O5 C22 1.465(4) . ? N1 C5 1.326(4) . ? N1 C6 1.461(4) . ? N1 H1 0.8600 . ? N2 C13 1.358(4) . ? N2 C14 1.458(4) . ? N2 H2 0.8600 . ? C1 C4 1.512(5) . ? C1 C2 1.519(5) . ? C1 C3 1.525(5) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C6 C11 1.497(5) . ? C6 C7 1.531(5) . ? C6 H6 0.9800 . ? C7 C8 1.533(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.427(7) . ? C8 C10 1.559(7) . ? C8 H8 0.9800 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.336(4) . ? C11 H11 0.9300 . ? C12 C13 1.479(4) . ? C12 H12 0.9300 . ? C14 C19 1.494(5) . ? C14 C15 1.542(5) . ? C14 H14 0.9800 . ? C15 C16 1.534(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.521(6) . ? C16 C18 1.527(6) . ? C16 H16 0.9800 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.326(5) . ? C19 H19 0.9300 . ? C20 C21 1.472(5) . ? C20 H20 0.9300 . ? C22 C23 1.493(7) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 O1 C1 120.7(2) . . ? C21 O5 C22 116.4(3) . . ? C5 N1 C6 122.7(2) . . ? C5 N1 H1 118.6 . . ? C6 N1 H1 118.6 . . ? C13 N2 C14 122.2(3) . . ? C13 N2 H2 118.9 . . ? C14 N2 H2 118.9 . . ? O1 C1 C4 110.1(3) . . ? O1 C1 C2 110.8(3) . . ? C4 C1 C2 113.6(3) . . ? O1 C1 C3 102.0(2) . . ? C4 C1 C3 110.3(3) . . ? C2 C1 C3 109.4(3) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O2 C5 N1 125.6(3) . . ? O2 C5 O1 124.1(3) . . ? N1 C5 O1 110.4(3) . . ? N1 C6 C11 109.2(2) . . ? N1 C6 C7 111.2(2) . . ? C11 C6 C7 111.2(3) . . ? N1 C6 H6 108.4 . . ? C11 C6 H6 108.4 . . ? C7 C6 H6 108.4 . . ? C6 C7 C8 114.7(3) . . ? C6 C7 H7A 108.6 . . ? C8 C7 H7A 108.6 . . ? C6 C7 H7B 108.6 . . ? C8 C7 H7B 108.6 . . ? H7A C7 H7B 107.6 . . ? C9 C8 C7 116.8(4) . . ? C9 C8 C10 111.6(4) . . ? C7 C8 C10 107.4(4) . . ? C9 C8 H8 106.9 . . ? C7 C8 H8 106.9 . . ? C10 C8 H8 106.9 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C6 124.7(3) . . ? C12 C11 H11 117.6 . . ? C6 C11 H11 117.6 . . ? C11 C12 C13 122.1(3) . . ? C11 C12 H12 119.0 . . ? C13 C12 H12 119.0 . . ? O3 C13 N2 122.6(3) . . ? O3 C13 C12 123.8(3) . . ? N2 C13 C12 113.6(3) . . ? N2 C14 C19 112.4(3) . . ? N2 C14 C15 108.6(3) . . ? C19 C14 C15 113.3(3) . . ? N2 C14 H14 107.4 . . ? C19 C14 H14 107.4 . . ? C15 C14 H14 107.4 . . ? C16 C15 C14 117.3(3) . . ? C16 C15 H15A 108.0 . . ? C14 C15 H15A 108.0 . . ? C16 C15 H15B 108.0 . . ? C14 C15 H15B 108.0 . . ? H15A C15 H15B 107.2 . . ? C17 C16 C18 110.9(3) . . ? C17 C16 C15 109.9(4) . . ? C18 C16 C15 112.0(3) . . ? C17 C16 H16 108.0 . . ? C18 C16 H16 108.0 . . ? C15 C16 H16 108.0 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 C14 127.6(3) . . ? C20 C19 H19 116.2 . . ? C14 C19 H19 116.2 . . ? C19 C20 C21 120.0(3) . . ? C19 C20 H20 120.0 . . ? C21 C20 H20 120.0 . . ? O4 C21 O5 123.0(3) . . ? O4 C21 C20 126.5(3) . . ? O5 C21 C20 110.5(3) . . ? O5 C22 C23 107.4(3) . . ? O5 C22 H22A 110.2 . . ? C23 C22 H22A 110.2 . . ? O5 C22 H22B 110.2 . . ? C23 C22 H22B 110.2 . . ? H22A C22 H22B 108.5 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 29.13 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.575 _refine_diff_density_min -0.373 _refine_diff_density_rms 0.059 # Attachment 'Boc-dgVal.cif' data_anudgval _database_code_depnum_ccdc_archive 'CCDC 825104' #TrackingRef 'Boc-dgVal.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic '(S,E)-ethyl 4-(tert-butoxycarbonylamino)-5-methylhex-2-enoate' _chemical_name_common Boc-dgV-OEt _chemical_formula_moiety 'C14 H25 N O4' _chemical_formula_sum 'C14 H25 N O4' _chemical_compound_source Synthesis _exptl_crystal_recrystallization_method Methanol _chemical_melting_point ? _exptl_crystal_description 'Retangular block' _exptl_crystal_colour Colorless _diffrn_ambient_temperature 200(2) _diffrn_ambient_pressure 101.325 _chemical_formula_weight 271.35 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 orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_int_tables_number 19 _chemical_absolute_configuration syn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.978(4) _cell_length_b 10.083(3) _cell_length_c 16.904(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1700.7(10) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.060 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.968 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Graphite Monochromator' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6738 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0460 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 27.92 _reflns_number_total 3650 _reflns_number_gt 1978 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1055P)^2^+0.0466P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(2) _refine_ls_number_reflns 3650 _refine_ls_number_parameters 178 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1149 _refine_ls_R_factor_gt 0.0581 _refine_ls_wR_factor_ref 0.1950 _refine_ls_wR_factor_gt 0.1589 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.028 _refine_ls_shift/su_mean 0.001 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 0.7383(2) 0.23515(18) 0.81612(14) 0.0717(6) Uani 1 1 d . . . O2 O 0.5956(2) 0.4107(2) 0.81259(17) 0.0834(7) Uani 1 1 d . . . O3 O 0.9845(4) 0.5727(3) 0.5878(2) 0.1163(10) Uani 1 1 d . . . O4 O 0.9354(3) 0.7733(3) 0.6367(2) 0.1093(10) Uani 1 1 d . . . N1 N 0.8124(2) 0.4336(2) 0.85101(16) 0.0653(7) Uani 1 1 d . . . H1 H 0.8835 0.3923 0.8659 0.078 Uiso 1 1 calc R . . C1 C 0.6390(3) 0.1420(3) 0.7809(2) 0.0674(8) Uani 1 1 d . . . C2 C 0.5176(4) 0.1286(4) 0.8342(3) 0.0940(12) Uani 1 1 d . . . H2A H 0.5459 0.1016 0.8860 0.141 Uiso 1 1 calc R . . H2B H 0.4578 0.0634 0.8127 0.141 Uiso 1 1 calc R . . H2C H 0.4724 0.2125 0.8376 0.141 Uiso 1 1 calc R . . C3 C 0.7191(4) 0.0130(3) 0.7788(3) 0.0946(12) Uani 1 1 d . . . H3A H 0.7994 0.0259 0.7485 0.142 Uiso 1 1 calc R . . H3B H 0.6660 -0.0555 0.7549 0.142 Uiso 1 1 calc R . . H3C H 0.7424 -0.0125 0.8318 0.142 Uiso 1 1 calc R . . C4 C 0.6040(4) 0.1849(4) 0.6986(2) 0.0874(10) Uani 1 1 d . . . H4A H 0.5657 0.2722 0.7001 0.131 Uiso 1 1 calc R . . H4B H 0.5404 0.1240 0.6763 0.131 Uiso 1 1 calc R . . H4C H 0.6836 0.1860 0.6666 0.131 Uiso 1 1 calc R . . C5 C 0.7057(3) 0.3640(3) 0.82536(18) 0.0589(7) Uani 1 1 d . . . C6 C 0.8088(3) 0.5780(3) 0.8537(2) 0.0721(9) Uani 1 1 d . . . H6 H 0.7142 0.6025 0.8593 0.086 Uiso 1 1 calc R . . C7 C 0.8803(5) 0.6332(4) 0.9274(3) 0.1063(13) Uani 1 1 d . . . H7 H 0.8672 0.7295 0.9265 0.128 Uiso 1 1 calc R . . C8 C 1.0256(5) 0.6109(6) 0.9260(4) 0.147(2) Uani 1 1 d . . . H8A H 1.0657 0.6517 0.9716 0.220 Uiso 1 1 calc R . . H8B H 1.0628 0.6491 0.8789 0.220 Uiso 1 1 calc R . . H8C H 1.0435 0.5174 0.9268 0.220 Uiso 1 1 calc R . . C9 C 0.8166(8) 0.5836(7) 1.0038(3) 0.161(2) Uani 1 1 d . . . H9A H 0.8310 0.4898 1.0087 0.242 Uiso 1 1 calc R . . H9B H 0.7221 0.6014 1.0028 0.242 Uiso 1 1 calc R . . H9C H 0.8565 0.6283 1.0481 0.242 Uiso 1 1 calc R . . C10 C 0.8557(3) 0.6408(3) 0.7790(2) 0.0753(10) Uani 1 1 d . . . H10 H 0.8551 0.7330 0.7777 0.090 Uiso 1 1 calc R . . C11 C 0.8981(3) 0.5809(3) 0.7146(2) 0.0748(9) Uani 1 1 d . . . H11 H 0.9017 0.4887 0.7141 0.090 Uiso 1 1 calc R . . C12 C 0.9397(4) 0.6535(5) 0.6437(3) 0.0869(11) Uani 1 1 d . . . C13 C 1.0259(8) 0.6337(8) 0.5136(4) 0.173(3) Uani 1 1 d D . . H13A H 0.9553 0.6227 0.4747 0.207 Uiso 1 1 calc R . . H13B H 1.0392 0.7280 0.5218 0.207 Uiso 1 1 calc R . . C14 C 1.1428(8) 0.5784(10) 0.4850(4) 0.202(4) Uani 1 1 d D . . H14A H 1.2039 0.5636 0.5280 0.303 Uiso 1 1 calc R . . H14B H 1.1830 0.6377 0.4474 0.303 Uiso 1 1 calc R . . H14C H 1.1229 0.4955 0.4596 0.303 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 0.0662(12) 0.0520(10) 0.0970(17) -0.0016(10) -0.0223(12) -0.0014(9) O2 0.0682(13) 0.0610(10) 0.121(2) -0.0049(13) -0.0212(13) 0.0054(10) O3 0.139(3) 0.117(2) 0.093(2) 0.0188(19) 0.0047(19) -0.006(2) O4 0.0924(19) 0.0828(17) 0.153(3) 0.0449(18) -0.0108(17) -0.0094(14) N1 0.0587(14) 0.0505(12) 0.0866(19) 0.0004(12) -0.0122(13) -0.0018(11) C1 0.0643(17) 0.0527(14) 0.085(2) -0.0026(17) -0.0128(17) -0.0075(13) C2 0.092(2) 0.087(2) 0.103(3) -0.005(2) 0.008(2) -0.029(2) C3 0.101(3) 0.0557(16) 0.127(3) -0.015(2) -0.020(2) -0.0049(18) C4 0.094(2) 0.087(2) 0.081(3) -0.004(2) -0.015(2) -0.0059(19) C5 0.0618(16) 0.0505(13) 0.0643(19) 0.0034(14) -0.0089(15) 0.0008(13) C6 0.0691(18) 0.0522(14) 0.095(3) -0.0106(17) -0.0054(18) -0.0019(14) C7 0.118(3) 0.086(2) 0.115(4) -0.026(2) -0.014(3) -0.014(2) C8 0.110(4) 0.155(5) 0.175(6) -0.051(4) -0.038(4) -0.014(3) C9 0.195(7) 0.186(6) 0.103(4) -0.028(4) 0.003(4) -0.030(5) C10 0.0690(19) 0.0494(14) 0.108(3) -0.002(2) -0.0145(19) -0.0018(15) C11 0.0719(19) 0.0556(15) 0.097(3) 0.0107(19) -0.0126(19) -0.0112(15) C12 0.063(2) 0.093(3) 0.105(3) 0.010(3) -0.0152(19) -0.0063(19) C13 0.198(7) 0.213(6) 0.107(4) 0.066(5) 0.032(4) 0.019(6) C14 0.170(7) 0.330(12) 0.106(4) 0.039(6) 0.031(4) 0.040(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 1.349(3) . ? O1 C1 1.489(3) . ? O2 C5 1.215(4) . ? O3 C12 1.325(5) . ? O3 C13 1.457(6) . ? O4 C12 1.214(5) . ? N1 C5 1.346(4) . ? N1 C6 1.458(4) . ? C1 C4 1.499(5) . ? C1 C2 1.515(5) . ? C1 C3 1.527(4) . ? C6 C10 1.489(5) . ? C6 C7 1.539(6) . ? C7 C8 1.467(7) . ? C7 C9 1.524(8) . ? C10 C11 1.314(5) . ? C11 C12 1.465(6) . ? C13 C14 1.381(9) . ? 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 O1 C1 119.6(2) . . ? C12 O3 C13 116.7(4) . . ? C5 N1 C6 120.7(3) . . ? O1 C1 C4 110.1(3) . . ? O1 C1 C2 110.5(3) . . ? C4 C1 C2 113.1(3) . . ? O1 C1 C3 101.4(2) . . ? C4 C1 C3 110.3(3) . . ? C2 C1 C3 110.9(3) . . ? O2 C5 N1 124.8(3) . . ? O2 C5 O1 124.8(3) . . ? N1 C5 O1 110.4(2) . . ? N1 C6 C10 112.9(3) . . ? N1 C6 C7 112.0(3) . . ? C10 C6 C7 112.8(3) . . ? C8 C7 C9 112.0(5) . . ? C8 C7 C6 113.0(4) . . ? C9 C7 C6 111.9(4) . . ? C11 C10 C6 127.5(3) . . ? C10 C11 C12 122.6(3) . . ? O4 C12 O3 123.7(5) . . ? O4 C12 C11 124.5(5) . . ? O3 C12 C11 111.8(4) . . ? C14 C13 O3 111.8(6) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.92 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.344 _refine_diff_density_min -0.160 _refine_diff_density_rms 0.036