Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2002 data_global _audit_creation_method SHELXL-97 _journal_coden_Cambridge 182 loop_ _publ_author_name 'Henrik Birkedal' 'Philip Pattison' 'Dieter Schwarzenback' _publ_contact_author_name 'Dr Henrik Birkedal' _publ_contact_author_address ; Department of Chemistry and Biochemistry University of California Santa Barbara California 93106 UNITED STATES OF AMERICA ; _publ_contact_author_email 'HBIRKEDAL@CHEM.UCSB.EDU' _publ_requested_journal 'Chemical Communications' _publ_section_title ; FGFG: a fully extended natural peptide ; data_fgfg _database_code_CSD 192545 _chemical_name_systematic ; ? ; _chemical_name_common 'PheGlyPheGly' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H26 N4 O5' _chemical_formula_weight 426.47 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' 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 5.0630(10) _cell_length_b 15.379(3) _cell_length_c 28.912(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2251.2(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.191(5) _exptl_crystal_size_mid 0.0134(10) _exptl_crystal_size_min 0.0134(10) _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.258 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.80080 _diffrn_radiation_type synchrotron _diffrn_radiation_source ; Swiss Norwegian Beam Line, European Synchrotron Radiation Facility ; _diffrn_radiation_monochromator ; Si(111) double crystal monochromator with bent second crystal for sagital focusing ; _diffrn_measurement_device_type 'MAR345' _diffrn_measurement_method '\f-scans' _diffrn_detector_area_resol_mean 6.667 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12283 _diffrn_reflns_av_R_equivalents 0.041 _diffrn_reflns_av_sigmaI/netI 0.0312 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 26.40 _reflns_number_total 1920 _reflns_number_gt 1795 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'HKL (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (Siemens, 1996)' _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^)+(0.048P)^2^+0.2933P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Fixed by known peptide conformation' _refine_ls_abs_structure_Flack 0.8(14) _refine_ls_number_reflns 1920 _refine_ls_number_parameters 281 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0329 _refine_ls_R_factor_gt 0.0298 _refine_ls_wR_factor_ref 0.0840 _refine_ls_wR_factor_gt 0.0810 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 0.1790(3) 1.08683(12) 0.42989(5) 0.0482(4) Uani 1 1 d . . . N1 N 0.4509(4) 1.15226(11) 0.50121(5) 0.0350(4) Uani 1 1 d . . . H11 H 0.2891 1.1309 0.5052 0.052 Uiso 1 1 calc R . . H12 H 0.4402 1.2058 0.4897 0.052 Uiso 1 1 calc R . . H13 H 0.5344 1.1537 0.5283 0.052 Uiso 1 1 calc R . . C1 C 0.4187(4) 1.07853(14) 0.42747(7) 0.0346(5) Uani 1 1 d . . . C1A C 0.5989(4) 1.09614(13) 0.46867(7) 0.0324(5) Uani 1 1 d . . . H1A H 0.7549 1.1279 0.4578 0.039 Uiso 1 1 calc R . . C1B C 0.6901(5) 1.01153(14) 0.49186(8) 0.0439(6) Uani 1 1 d . . . H1B1 H 0.7945 0.9788 0.4698 0.053 Uiso 1 1 calc R . . H1B2 H 0.8045 1.0263 0.5176 0.053 Uiso 1 1 calc R . . C1G C 0.4715(5) 0.95385(15) 0.50949(8) 0.0475(6) Uani 1 1 d . . . C1D1 C 0.3552(6) 0.89145(16) 0.48155(10) 0.0598(7) Uani 1 1 d . . . H1D1 H 0.4137 0.8847 0.4513 0.072 Uiso 1 1 calc R . . C1D2 C 0.3788(5) 0.96146(18) 0.55442(9) 0.0564(7) Uani 1 1 d . . . H1D2 H 0.4533 1.0027 0.5740 0.068 Uiso 1 1 calc R . . C1E1 C 0.1529(6) 0.83870(17) 0.49795(12) 0.0708(9) Uani 1 1 d . . . H1E1 H 0.0767 0.7973 0.4787 0.085 Uiso 1 1 calc R . . C1E2 C 0.1771(7) 0.9088(2) 0.57077(10) 0.0701(8) Uani 1 1 d . . . H1E2 H 0.1173 0.9149 0.6010 0.084 Uiso 1 1 calc R . . C1Z C 0.0663(6) 0.84766(19) 0.54232(12) 0.0710(9) Uani 1 1 d . . . H1Z H -0.0684 0.8122 0.5533 0.085 Uiso 1 1 calc R . . O2 O 0.8116(3) 0.96774(14) 0.32353(6) 0.0610(5) Uani 1 1 d . . . N2 N 0.5407(4) 1.04905(14) 0.38966(6) 0.0486(5) Uani 1 1 d . . . H2 H 0.7105 1.0478 0.3889 0.058 Uiso 1 1 calc R . . C2 C 0.5718(5) 0.96871(17) 0.31812(7) 0.0436(6) Uani 1 1 d . . . C2A C 0.3929(5) 1.0193(2) 0.35007(8) 0.0549(7) Uani 1 1 d . . . H2A1 H 0.3191 1.0687 0.3337 0.066 Uiso 1 1 calc R . . H2A2 H 0.2483 0.9825 0.3602 0.066 Uiso 1 1 calc R . . O3 O 0.1848(3) 0.87383(13) 0.20824(5) 0.0530(5) Uani 1 1 d . . . N3 N 0.4497(4) 0.92710(12) 0.28369(5) 0.0408(5) Uani 1 1 d . . . H3 H 0.2804 0.9296 0.2817 0.049 Uiso 1 1 calc R . . C3 C 0.4262(4) 0.86669(15) 0.20673(7) 0.0376(5) Uani 1 1 d . . . C3A C 0.5974(4) 0.87760(15) 0.24949(7) 0.0374(5) Uani 1 1 d . . . H3A H 0.7544 0.9112 0.2409 0.045 Uiso 1 1 calc R . . C3B C 0.6886(5) 0.78877(16) 0.26858(8) 0.0482(6) Uani 1 1 d . . . H3B1 H 0.7919 0.7597 0.2449 0.058 Uiso 1 1 calc R . . H3B2 H 0.8042 0.7990 0.2948 0.058 Uiso 1 1 calc R . . C3G C 0.4696(5) 0.72833(16) 0.28369(9) 0.0520(6) Uani 1 1 d . . . C3D1 C 0.3546(6) 0.66994(18) 0.25313(11) 0.0687(8) Uani 1 1 d . . . H3D1 H 0.4105 0.6684 0.2225 0.082 Uiso 1 1 calc R . . C3D2 C 0.3792(6) 0.7283(2) 0.32902(9) 0.0689(8) Uani 1 1 d . . . H3D2 H 0.4528 0.7667 0.3503 0.083 Uiso 1 1 calc R . . C3E1 C 0.1569(8) 0.6138(2) 0.26790(15) 0.0853(10) Uani 1 1 d . . . H3E1 H 0.0809 0.5753 0.2470 0.102 Uiso 1 1 calc R . . C3E2 C 0.1813(8) 0.6721(3) 0.34322(13) 0.0895(11) Uani 1 1 d . . . H3E2 H 0.1220 0.6735 0.3737 0.107 Uiso 1 1 calc R . . C3Z C 0.0732(8) 0.6146(2) 0.31256(16) 0.0905(11) Uani 1 1 d . . . H3Z H -0.0572 0.5761 0.3222 0.109 Uiso 1 1 calc R . . O4' O 0.8377(3) 0.84601(15) 0.09014(5) 0.0652(6) Uani 1 1 d . . . N4 N 0.5578(4) 0.84494(14) 0.16863(5) 0.0485(5) Uani 1 1 d . . . H4 H 0.7275 0.8432 0.1695 0.058 Uiso 1 1 calc R . . O4" O 0.5043(3) 0.80500(10) 0.04620(4) 0.0434(4) Uani 1 1 d . . . C4 C 0.6047(4) 0.82525(15) 0.08458(7) 0.0380(5) Uani 1 1 d . . . C4A C 0.4238(5) 0.8239(2) 0.12561(7) 0.0566(7) Uani 1 1 d . . . H4A1 H 0.2822 0.8654 0.1206 0.068 Uiso 1 1 calc R . . H4A2 H 0.3451 0.7666 0.1283 0.068 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 0.0272(9) 0.0790(12) 0.0385(8) -0.0118(8) -0.0004(7) 0.0040(9) N1 0.0305(9) 0.0488(10) 0.0257(8) -0.0013(7) -0.0008(8) 0.0021(8) C1 0.0302(13) 0.0434(11) 0.0303(11) -0.0029(9) 0.0038(9) -0.0013(10) C1A 0.0255(10) 0.0429(11) 0.0290(10) -0.0029(8) 0.0024(9) 0.0005(10) C1B 0.0315(12) 0.0493(12) 0.0509(13) 0.0016(10) -0.0010(12) 0.0045(11) C1G 0.0357(13) 0.0443(12) 0.0624(14) 0.0100(11) -0.0041(12) 0.0090(11) C1D1 0.0513(16) 0.0483(13) 0.0796(18) -0.0025(13) 0.0060(15) 0.0053(14) C1D2 0.0469(15) 0.0639(15) 0.0584(14) 0.0174(13) -0.0066(13) -0.0051(14) C1E1 0.0583(18) 0.0433(14) 0.111(3) -0.0012(15) -0.0013(19) -0.0049(14) C1E2 0.0616(18) 0.081(2) 0.0671(17) 0.0247(16) 0.0030(16) -0.0079(18) C1Z 0.0552(18) 0.0566(16) 0.101(2) 0.0284(16) 0.0030(19) -0.0036(15) O2 0.0296(10) 0.1046(14) 0.0489(9) -0.0304(10) -0.0017(8) -0.0005(10) N2 0.0269(10) 0.0823(14) 0.0366(10) -0.0221(9) 0.0018(9) -0.0028(11) C2 0.0327(14) 0.0672(15) 0.0309(11) -0.0094(11) 0.0037(11) -0.0007(11) C2A 0.0383(14) 0.0872(18) 0.0393(12) -0.0268(12) -0.0022(11) 0.0026(14) O3 0.0298(9) 0.0957(13) 0.0334(8) -0.0102(8) 0.0014(8) 0.0043(9) N3 0.0278(10) 0.0653(12) 0.0293(9) -0.0119(8) -0.0009(8) -0.0009(9) C3 0.0301(13) 0.0537(13) 0.0288(11) -0.0030(10) 0.0025(10) 0.0002(11) C3A 0.0291(11) 0.0561(12) 0.0271(10) -0.0074(9) 0.0028(10) 0.0008(10) C3B 0.0371(12) 0.0673(15) 0.0402(12) -0.0010(11) -0.0015(11) 0.0066(13) C3G 0.0431(14) 0.0576(15) 0.0554(14) 0.0079(12) -0.0034(13) 0.0116(13) C3D1 0.0647(19) 0.0592(16) 0.0823(19) -0.0081(15) 0.0048(17) 0.0044(16) C3D2 0.0600(18) 0.094(2) 0.0522(15) 0.0190(15) -0.0039(14) -0.0043(18) C3E1 0.078(2) 0.0580(18) 0.120(3) -0.0049(19) -0.010(2) 0.0022(18) C3E2 0.073(2) 0.118(3) 0.078(2) 0.041(2) 0.0015(19) -0.008(2) C3Z 0.068(2) 0.076(2) 0.127(3) 0.036(2) -0.001(2) -0.0037(19) O4' 0.0342(10) 0.1317(18) 0.0298(8) -0.0078(9) 0.0006(8) -0.0125(11) N4 0.0284(10) 0.0902(15) 0.0270(9) -0.0121(9) 0.0013(8) 0.0003(11) O4" 0.0436(9) 0.0608(9) 0.0258(7) -0.0093(6) -0.0069(7) 0.0061(8) C4 0.0347(12) 0.0513(12) 0.0280(11) -0.0020(9) -0.0031(9) 0.0035(11) C4A 0.0400(13) 0.103(2) 0.0264(11) -0.0155(13) 0.0007(11) -0.0095(15) _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 C1 1.222(3) . ? N1 C1A 1.481(3) . ? C1 N2 1.335(3) . ? C1 C1A 1.525(3) . ? C1A C1B 1.535(3) . ? C1B C1G 1.507(3) . ? C1G C1D1 1.386(4) . ? C1G C1D2 1.386(4) . ? C1D1 C1E1 1.390(4) . ? C1D2 C1E2 1.386(4) . ? C1E1 C1Z 1.363(4) . ? C1E2 C1Z 1.369(4) . ? O2 C2 1.224(3) . ? N2 C2A 1.442(3) . ? C2 N3 1.335(3) . ? C2 C2A 1.509(3) . ? O3 C3 1.228(3) . ? N3 C3A 1.455(3) . ? C3 N4 1.330(3) . ? C3 C3A 1.519(3) . ? C3A C3B 1.544(3) . ? C3B C3G 1.512(4) . ? C3G C3D1 1.388(4) . ? C3G C3D2 1.388(4) . ? C3D1 C3E1 1.389(4) . ? C3D2 C3E2 1.386(5) . ? C3E1 C3Z 1.359(5) . ? C3E2 C3Z 1.366(5) . ? O4' C4 1.232(3) . ? N4 C4A 1.453(3) . ? O4" C4 1.260(2) . ? C4 C4A 1.499(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 O1 C1 N2 122.8(2) . . ? O1 C1 C1A 122.08(19) . . ? N2 C1 C1A 115.01(19) . . ? N1 C1A C1 107.27(17) . . ? N1 C1A C1B 111.63(16) . . ? C1 C1A C1B 111.75(18) . . ? C1G C1B C1A 115.22(19) . . ? C1D1 C1G C1D2 117.4(2) . . ? C1D1 C1G C1B 121.5(2) . . ? C1D2 C1G C1B 121.1(2) . . ? C1G C1D1 C1E1 121.2(3) . . ? C1G C1D2 C1E2 121.3(3) . . ? C1Z C1E1 C1D1 119.9(3) . . ? C1Z C1E2 C1D2 119.9(3) . . ? C1E1 C1Z C1E2 120.2(3) . . ? C1 N2 C2A 121.2(2) . . ? O2 C2 N3 123.3(2) . . ? O2 C2 C2A 121.5(2) . . ? N3 C2 C2A 115.2(2) . . ? N2 C2A C2 109.8(2) . . ? C2 N3 C3A 121.28(19) . . ? O3 C3 N4 123.4(2) . . ? O3 C3 C3A 121.94(19) . . ? N4 C3 C3A 114.58(19) . . ? N3 C3A C3 108.50(18) . . ? N3 C3A C3B 111.95(17) . . ? C3 C3A C3B 111.33(19) . . ? C3G C3B C3A 115.3(2) . . ? C3D1 C3G C3D2 117.6(3) . . ? C3D1 C3G C3B 121.4(2) . . ? C3D2 C3G C3B 121.0(3) . . ? C3G C3D1 C3E1 120.6(3) . . ? C3E2 C3D2 C3G 121.2(3) . . ? C3Z C3E1 C3D1 120.8(4) . . ? C3Z C3E2 C3D2 120.1(3) . . ? C3E1 C3Z C3E2 119.8(4) . . ? C3 N4 C4A 122.1(2) . . ? O4' C4 O4" 124.4(2) . . ? O4' C4 C4A 119.02(19) . . ? O4" C4 C4A 116.6(2) . . ? N4 C4A C4 112.90(19) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H11 O1 0.89 2.35 2.676(2) 101.9 . N2 H2 O2 0.86 2.31 2.665(2) 104.7 . N3 H3 O3 0.86 2.34 2.688(2) 104.5 . N4 H4 O4' 0.86 2.36 2.675(2) 102.0 . N1 H13 O4' 0.89 1.90 2.785(2) 171.4 2_675 N1 H13 O4" 0.89 2.47 3.119(3) 129.7 2_675 N1 H11 O4" 0.89 2.14 2.727(2) 122.7 2_575 N1 H12 O4" 0.89 1.87 2.729(2) 162.7 3_655 C1A H1A O1 0.98 2.38 3.147(3) 134.7 1_655 C3A H3A O3 0.98 2.44 3.205(3) 134.3 1_655 C2A H2A2 O2 0.97 2.46 3.143(3) 127.0 1_455 C4A H4A1 O4' 0.97 2.44 3.158(3) 131.0 1_455 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.40 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.162 _refine_diff_density_min -0.119 _refine_diff_density_rms 0.026 #===END