# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 data_23 _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'A. Boa' 'Patrick D. Bailey' 'Neill Bannister' 'Marine Bernad' 'Sophie Blanchard' _publ_contact_author_name 'Prof. Patrick D. Bailey' _publ_contact_author_address ; Department of Chemistry Heriot-Watt University Edinburgh EH14 4AS ; _publ_contact_author_email 'P.D.Bailey@hw.ac.uk' _publ_section_title ; Synthesis of conformationally constrained amino acid and peptide derivatives ; _database_code_CSD 135218 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C20 H22 N2 O3' _chemical_formula_weight 338.40 _chemical_melting_point ? _chemical_compound_source ? 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' 'O' 'O' 0.0106 0.0060 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 8.8130(10) _cell_length_b 11.418(2) _cell_length_c 18.102(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.540(10) _cell_angle_gamma 90.00 _cell_volume 1770.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 42 _cell_measurement_theta_min 9.378 _cell_measurement_theta_max 25.021 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.52 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.269 _exptl_crystal_density_method ? _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4173 _diffrn_reflns_av_R_equivalents 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0336 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3115 _reflns_number_observed 2579 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens XSCANS' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0409P)^2^+0.5440P] 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 3115 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0476 _refine_ls_R_factor_obs 0.0372 _refine_ls_wR_factor_all 0.1010 _refine_ls_wR_factor_obs 0.0933 _refine_ls_goodness_of_fit_all 1.022 _refine_ls_goodness_of_fit_obs 1.046 _refine_ls_restrained_S_all 1.022 _refine_ls_restrained_S_obs 1.046 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N1 N 0.26157(14) 0.39963(10) 0.12165(6) 0.0242(3) Uani 1 d . . N2 N 0.04310(14) 0.24514(10) 0.16142(6) 0.0246(3) Uani 1 d . . O2 O 0.36076(12) 0.25168(9) 0.06510(6) 0.0299(3) Uani 1 d . . O3 O 0.1558(2) 0.54351(10) 0.17931(7) 0.0461(3) Uani 1 d . . O4 O -0.04774(13) 0.39581(10) 0.22044(6) 0.0368(3) Uani 1 d . . C1 C 0.1622(2) 0.19323(12) 0.12595(8) 0.0245(3) Uani 1 d . . C2 C 0.2679(2) 0.28356(12) 0.10082(7) 0.0230(3) Uani 1 d . . C3 C 0.1589(2) 0.44188(13) 0.16259(8) 0.0288(3) Uani 1 d . . C4 C 0.0432(2) 0.35650(13) 0.18498(8) 0.0263(3) Uani 1 d . . C5 C 0.0822(2) 0.12315(13) 0.05427(8) 0.0284(3) Uani 1 d . . H5A H 0.1617(2) 0.08453(13) 0.03401(8) 0.034 Uiso 1 calc R . H5B H 0.0170(2) 0.06289(13) 0.06864(8) 0.034 Uiso 1 calc R . C6 C -0.0164(2) 0.19790(13) -0.00683(9) 0.0304(3) Uani 1 d . . H6A H -0.0956(2) 0.24162(13) 0.00582(9) 0.037 Uiso 1 calc R . C7 C 0.0009(2) 0.20626(15) -0.07690(9) 0.0373(4) Uani 1 d . . H7A H 0.0789(2) 0.16386(15) -0.09169(9) 0.045 Uiso 1 calc R . H7B H -0.0648(2) 0.25457(15) -0.11162(9) 0.045 Uiso 1 calc R . C8 C 0.3755(2) 0.48209(13) 0.10250(8) 0.0299(3) Uani 1 d . . H8A H 0.4747(2) 0.44226(13) 0.10822(8) 0.036 Uiso 1 calc R . H8B H 0.3908(2) 0.54651(13) 0.13842(8) 0.036 Uiso 1 calc R . C9 C 0.3274(2) 0.53069(13) 0.02362(9) 0.0311(3) Uani 1 d . . H9A H 0.3910(2) 0.58876(13) 0.01104(9) 0.037 Uiso 1 calc R . C10 C 0.2057(2) 0.50034(14) -0.02956(9) 0.0367(4) Uani 1 d . . H10A H 0.1383(2) 0.44268(14) -0.02000(9) 0.044 Uiso 1 calc R . H10B H 0.1867(2) 0.53644(14) -0.07689(9) 0.044 Uiso 1 calc R . C11 C -0.0735(2) 0.16683(14) 0.18309(9) 0.0325(3) Uani 1 d . . H11A H -0.0872(2) 0.18986(14) 0.23270(9) 0.039 Uiso 1 calc R . H11B H -0.0339(2) 0.08723(14) 0.18708(9) 0.039 Uiso 1 calc R . C12 C -0.2287(2) 0.1696(2) 0.12733(10) 0.0382(4) Uani 1 d . . H12A H -0.2691(2) 0.2424(2) 0.10969(10) 0.046 Uiso 1 calc R . C13 C -0.3114(2) 0.0764(2) 0.10172(12) 0.0508(5) Uani 1 d . . H13A H -0.2743(2) 0.0024(2) 0.11821(12) 0.061 Uiso 1 calc R . H13B H -0.4070(2) 0.0844(2) 0.06708(12) 0.061 Uiso 1 calc R . C14 C 0.2731(2) 0.11218(13) 0.18403(8) 0.0290(3) Uani 1 d . . H14A H 0.2118(2) 0.05114(13) 0.20038(8) 0.035 Uiso 1 calc R . H14B H 0.3462(2) 0.07478(13) 0.15893(8) 0.035 Uiso 1 calc R . C15 C 0.3634(2) 0.17745(13) 0.25301(8) 0.0280(3) Uani 1 d . . C16 C 0.5039(2) 0.23203(14) 0.25159(9) 0.0328(4) Uani 1 d . . H16A H 0.5434(2) 0.22594(14) 0.20837(9) 0.039 Uiso 1 calc R . C17 C 0.5861(2) 0.29534(15) 0.31352(10) 0.0410(4) Uani 1 d . . H17A H 0.6792(2) 0.33218(15) 0.31147(10) 0.049 Uiso 1 calc R . C18 C 0.5294(2) 0.3035(2) 0.37810(10) 0.0461(5) Uani 1 d . . H18A H 0.5843(2) 0.3457(2) 0.41979(10) 0.055 Uiso 1 calc R . C19 C 0.3915(2) 0.2491(2) 0.38085(9) 0.0464(5) Uani 1 d . . H19A H 0.3539(2) 0.2542(2) 0.42468(9) 0.056 Uiso 1 calc R . C20 C 0.3078(2) 0.1867(2) 0.31860(9) 0.0370(4) Uani 1 d . . H20A H 0.2141(2) 0.1509(2) 0.32084(9) 0.044 Uiso 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 N1 0.0285(6) 0.0218(6) 0.0225(6) -0.0018(5) 0.0066(5) -0.0023(5) N2 0.0282(6) 0.0226(6) 0.0243(6) 0.0035(5) 0.0089(5) 0.0016(5) O2 0.0321(6) 0.0318(6) 0.0275(5) -0.0011(4) 0.0106(4) 0.0049(5) O3 0.0644(8) 0.0250(6) 0.0579(8) -0.0140(6) 0.0323(7) -0.0058(6) O4 0.0438(6) 0.0358(6) 0.0367(6) -0.0027(5) 0.0213(5) 0.0045(5) C1 0.0298(7) 0.0198(7) 0.0239(7) 0.0000(6) 0.0064(6) 0.0033(6) C2 0.0256(7) 0.0243(7) 0.0172(6) 0.0000(5) 0.0013(5) 0.0032(6) C3 0.0360(8) 0.0252(8) 0.0259(7) -0.0044(6) 0.0089(6) 0.0006(6) C4 0.0314(7) 0.0273(7) 0.0209(7) 0.0003(6) 0.0072(6) 0.0051(6) C5 0.0344(8) 0.0218(7) 0.0286(7) -0.0041(6) 0.0068(6) -0.0007(6) C6 0.0301(8) 0.0270(8) 0.0317(8) -0.0043(6) 0.0023(6) -0.0004(6) C7 0.0372(8) 0.0386(9) 0.0335(8) 0.0013(7) 0.0030(7) -0.0044(7) C8 0.0303(8) 0.0287(8) 0.0310(8) -0.0043(6) 0.0079(6) -0.0073(6) C9 0.0354(8) 0.0250(7) 0.0355(8) 0.0008(6) 0.0136(7) -0.0028(6) C10 0.0426(9) 0.0316(8) 0.0350(8) 0.0079(7) 0.0071(7) -0.0001(7) C11 0.0383(8) 0.0280(8) 0.0353(8) 0.0073(7) 0.0166(7) -0.0005(7) C12 0.0349(8) 0.0368(9) 0.0472(9) 0.0071(8) 0.0180(7) 0.0025(7) C13 0.0381(10) 0.0505(11) 0.0661(13) -0.0046(10) 0.0169(9) -0.0041(9) C14 0.0345(8) 0.0230(7) 0.0295(7) 0.0032(6) 0.0071(6) 0.0055(6) C15 0.0319(8) 0.0257(7) 0.0251(7) 0.0068(6) 0.0040(6) 0.0102(6) C16 0.0336(8) 0.0340(8) 0.0300(8) 0.0070(7) 0.0061(6) 0.0075(7) C17 0.0387(9) 0.0337(9) 0.0436(10) 0.0052(8) -0.0047(8) 0.0041(7) C18 0.0523(11) 0.0414(10) 0.0350(9) -0.0080(8) -0.0091(8) 0.0158(9) C19 0.0542(11) 0.0592(12) 0.0246(8) 0.0009(8) 0.0067(7) 0.0252(9) C20 0.0373(8) 0.0448(10) 0.0288(8) 0.0093(7) 0.0076(7) 0.0125(8) _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 N1 C2 1.383(2) . ? N1 C3 1.384(2) . ? N1 C8 1.475(2) . ? N2 C4 1.341(2) . ? N2 C1 1.477(2) . ? N2 C11 1.482(2) . ? O2 C2 1.212(2) . ? O3 C3 1.201(2) . ? O4 C4 1.224(2) . ? C1 C2 1.528(2) . ? C1 C5 1.547(2) . ? C1 C14 1.561(2) . ? C3 C4 1.532(2) . ? C5 C6 1.502(2) . ? C6 C7 1.316(2) . ? C8 C9 1.498(2) . ? C9 C10 1.309(2) . ? C11 C12 1.498(2) . ? C12 C13 1.312(3) . ? C14 C15 1.511(2) . ? C15 C20 1.391(2) . ? C15 C16 1.392(2) . ? C16 C17 1.387(2) . ? C17 C18 1.378(3) . ? C18 C19 1.376(3) . ? C19 C20 1.390(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C3 123.59(12) . . ? C2 N1 C8 118.34(12) . . ? C3 N1 C8 118.00(12) . . ? C4 N2 C1 124.83(12) . . ? C4 N2 C11 115.90(12) . . ? C1 N2 C11 118.69(11) . . ? N2 C1 C2 113.78(11) . . ? N2 C1 C5 109.96(11) . . ? C2 C1 C5 106.82(11) . . ? N2 C1 C14 109.99(11) . . ? C2 C1 C14 105.74(11) . . ? C5 C1 C14 110.43(11) . . ? O2 C2 N1 120.57(13) . . ? O2 C2 C1 119.40(13) . . ? N1 C2 C1 119.97(12) . . ? O3 C3 N1 121.89(14) . . ? O3 C3 C4 119.47(14) . . ? N1 C3 C4 118.62(12) . . ? O4 C4 N2 124.25(14) . . ? O4 C4 C3 117.62(13) . . ? N2 C4 C3 118.04(12) . . ? C6 C5 C1 113.28(12) . . ? C7 C6 C5 125.00(15) . . ? N1 C8 C9 113.86(12) . . ? C10 C9 C8 127.08(14) . . ? N2 C11 C12 112.87(12) . . ? C13 C12 C11 124.4(2) . . ? C15 C14 C1 112.95(12) . . ? C20 C15 C16 118.35(15) . . ? C20 C15 C14 121.37(14) . . ? C16 C15 C14 120.27(14) . . ? C17 C16 C15 121.1(2) . . ? C18 C17 C16 119.8(2) . . ? C19 C18 C17 120.0(2) . . ? C18 C19 C20 120.5(2) . . ? C19 C20 C15 120.3(2) . . ? _refine_diff_density_max 0.187 _refine_diff_density_min -0.165 _refine_diff_density_rms 0.036