# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Dr Sandeep Verma' _publ_contact_author_address ; Department of Chemistry Indian Institute of Technology-Kanpur Kanpur UP 208016 INDIA ; _publ_contact_author_email SVERMA@IITK.AC.IN _publ_section_title ; Enforcing Solution Phase Nanoscopic Aggregation in a Palindromic Tripeptide ; loop_ _publ_author_name 'Sandeep Verma' 'Alok Jain' P.K.Krishna C.S.Purohit R.Sankararamakrishnan data_BocGPGOMe _database_code_depnum_ccdc_archive 'CCDC 249980' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Boc-glycilprolylglycine methylester' _chemical_melting_point 181 _chemical_formula_moiety 'C15 H25 N3 O6' _chemical_formula_sum 'C15 H25 N3 O6' _chemical_formula_weight 343.38 _chemical_absolute_configuration rmad 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+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 5.9752(4) _cell_length_b 9.0939(7) _cell_length_c 32.092(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1743.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used all _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 28.3 _exptl_crystal_description 'Plate like' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.9800 _exptl_absorpt_correction_T_max 0.9899 _exptl_absorpt_process_details '(North et al., 1968)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area Detector' _diffrn_measurement_method 'Phi-Omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <0.05 _diffrn_reflns_number 11645 _diffrn_reflns_av_R_equivalents 0.0348 _diffrn_reflns_av_sigmaI/netI 0.0466 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -42 _diffrn_reflns_limit_l_max 42 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 28.29 _reflns_number_total 4294 _reflns_number_gt 3854 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 5.628 (Bruker, 2003)' _computing_cell_refinement 'SMART 5.628 (Bruker, 2003)' _computing_data_reduction 'SAINT+ 6.45 (Bruker, 2003)' _computing_structure_solution Sir92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 2.1 e' _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^)+(0.0621P)^2^+0.0133P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_number_reflns 4294 _refine_ls_number_parameters 220 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0539 _refine_ls_R_factor_gt 0.0476 _refine_ls_wR_factor_ref 0.1111 _refine_ls_wR_factor_gt 0.1079 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 0.8700(2) 0.65918(14) 0.63329(4) 0.0207(3) Uani 1 1 d . . . O2 O 0.6237(2) 0.46815(14) 0.63034(4) 0.0251(3) Uani 1 1 d . . . O3 O 0.52361(19) 0.72769(13) 0.75908(4) 0.0196(3) Uani 1 1 d . . . O4 O 0.3970(2) 0.44676(13) 0.83711(4) 0.0232(3) Uani 1 1 d . . . O5 O 0.4977(2) 0.5572(2) 0.97753(4) 0.0455(5) Uani 1 1 d . . . N1 N 0.6055(2) 0.64061(16) 0.68086(4) 0.0193(3) Uani 1 1 d . . . H1 H 0.6636 0.7194 0.6910 0.023 Uiso 1 1 calc R . . N2 N 0.2130(2) 0.58936(16) 0.76637(4) 0.0175(3) Uani 1 1 d . . . N3 N 0.3952(2) 0.66421(16) 0.87089(4) 0.0193(3) Uani 1 1 d . . . H3 H 0.3524 0.7545 0.8703 0.023 Uiso 1 1 calc R . . C1 C 1.1396(3) 0.7532(2) 0.58835(6) 0.0302(4) Uani 1 1 d . . . H1A H 1.2476 0.7406 0.6102 0.045 Uiso 1 1 calc R . . H1B H 1.0689 0.8475 0.5912 0.045 Uiso 1 1 calc R . . H1C H 1.2133 0.7476 0.5618 0.045 Uiso 1 1 calc R . . C2 C 1.0723(3) 0.4818(2) 0.58884(6) 0.0278(4) Uani 1 1 d . . . H2A H 0.9591 0.4073 0.5910 0.042 Uiso 1 1 calc R . . H2B H 1.1773 0.4710 0.6113 0.042 Uiso 1 1 calc R . . H2C H 1.1489 0.4719 0.5627 0.042 Uiso 1 1 calc R . . C3 C 0.7837(3) 0.6542(2) 0.55855(5) 0.0276(4) Uani 1 1 d . . . H3A H 0.7138 0.7483 0.5624 0.041 Uiso 1 1 calc R . . H3B H 0.6734 0.5780 0.5612 0.041 Uiso 1 1 calc R . . H3C H 0.8498 0.6499 0.5313 0.041 Uiso 1 1 calc R . . C4 C 0.9638(3) 0.6328(2) 0.59128(5) 0.0218(4) Uani 1 1 d . . . C5 C 0.6933(3) 0.58046(18) 0.64655(5) 0.0169(3) Uani 1 1 d . . . C6 C 0.4142(3) 0.57477(19) 0.70112(5) 0.0173(3) Uani 1 1 d . . . H6A H 0.4335 0.4690 0.7026 0.021 Uiso 1 1 calc R . . H6B H 0.2798 0.5951 0.6852 0.021 Uiso 1 1 calc R . . C7 C 0.3907(3) 0.63743(18) 0.74475(5) 0.0155(3) Uani 1 1 d . . . C8 C 0.0447(3) 0.4814(2) 0.75268(5) 0.0208(4) Uani 1 1 d . . . H8A H 0.1156 0.3928 0.7422 0.025 Uiso 1 1 calc R . . H8B H -0.0504 0.5221 0.7311 0.025 Uiso 1 1 calc R . . C9 C -0.0896(3) 0.4494(2) 0.79226(5) 0.0234(4) Uani 1 1 d . . . H9A H -0.2453 0.4299 0.7857 0.028 Uiso 1 1 calc R . . H9B H -0.0282 0.3658 0.8071 0.028 Uiso 1 1 calc R . . C10 C -0.0657(3) 0.5905(2) 0.81775(5) 0.0211(4) Uani 1 1 d . . . H10A H -0.0850 0.5708 0.8472 0.025 Uiso 1 1 calc R . . H10B H -0.1749 0.6632 0.8091 0.025 Uiso 1 1 calc R . . C11 C 0.1732(3) 0.64334(19) 0.80853(5) 0.0160(3) Uani 1 1 d . . . H11 H 0.1817 0.7509 0.8094 0.019 Uiso 1 1 calc R . . C12 C 0.3360(3) 0.57484(18) 0.83951(5) 0.0155(3) Uani 1 1 d . . . C13 C 0.5276(3) 0.6137(2) 0.90535(5) 0.0213(4) Uani 1 1 d . . . H13A H 0.6440 0.6858 0.9106 0.026 Uiso 1 1 calc R . . H13B H 0.6008 0.5230 0.8972 0.026 Uiso 1 1 calc R . . C14 C 0.4041(3) 0.5866(2) 0.94565(5) 0.0209(4) Uani 1 1 d . . . O6 O 0.1831(2) 0.59692(17) 0.94244(4) 0.0299(3) Uani 1 1 d . . . C15 C 0.0621(3) 0.5711(3) 0.98072(6) 0.0369(5) Uani 1 1 d . . . H15A H -0.0956 0.5806 0.9757 0.055 Uiso 1 1 calc R . . H15B H 0.1077 0.6417 1.0013 0.055 Uiso 1 1 calc R . . H15C H 0.0939 0.4737 0.9906 0.055 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0203(6) 0.0234(6) 0.0184(5) -0.0047(5) 0.0058(5) -0.0042(5) O2 0.0306(7) 0.0190(7) 0.0257(6) -0.0054(5) 0.0074(6) -0.0059(6) O3 0.0192(6) 0.0199(6) 0.0198(6) -0.0014(5) 0.0007(5) -0.0043(5) O4 0.0241(7) 0.0165(6) 0.0291(6) -0.0012(5) -0.0047(5) 0.0031(5) O5 0.0211(7) 0.0933(14) 0.0220(7) 0.0166(8) -0.0016(6) 0.0041(9) N1 0.0226(7) 0.0171(7) 0.0182(6) -0.0035(5) 0.0060(6) -0.0047(6) N2 0.0167(7) 0.0200(7) 0.0159(6) -0.0008(5) 0.0015(5) -0.0030(6) N3 0.0242(7) 0.0165(7) 0.0172(7) 0.0002(5) -0.0026(6) 0.0043(6) C1 0.0252(10) 0.0370(11) 0.0283(9) -0.0015(9) 0.0073(8) -0.0069(9) C2 0.0252(10) 0.0313(10) 0.0267(9) -0.0045(8) 0.0077(8) 0.0044(8) C3 0.0258(10) 0.0341(11) 0.0228(9) 0.0032(8) -0.0002(7) 0.0018(9) C4 0.0221(9) 0.0269(9) 0.0163(8) -0.0020(7) 0.0064(7) -0.0007(7) C5 0.0174(8) 0.0155(8) 0.0178(7) 0.0036(6) 0.0006(6) 0.0018(7) C6 0.0188(8) 0.0167(8) 0.0163(7) 0.0008(6) 0.0020(6) -0.0014(7) C7 0.0145(7) 0.0144(8) 0.0177(7) 0.0029(6) -0.0008(6) 0.0026(6) C8 0.0167(9) 0.0232(9) 0.0224(9) -0.0019(7) -0.0016(7) -0.0028(7) C9 0.0158(8) 0.0277(10) 0.0265(9) 0.0029(8) 0.0003(7) -0.0042(7) C10 0.0153(8) 0.0276(10) 0.0205(8) 0.0033(7) 0.0029(6) 0.0021(7) C11 0.0159(8) 0.0166(8) 0.0154(7) 0.0013(6) 0.0023(6) 0.0016(6) C12 0.0137(8) 0.0169(8) 0.0160(7) 0.0014(6) 0.0040(6) -0.0013(6) C13 0.0195(9) 0.0255(9) 0.0188(8) 0.0016(7) -0.0014(7) 0.0003(7) C14 0.0184(8) 0.0247(9) 0.0194(8) -0.0013(7) -0.0030(7) 0.0008(7) O6 0.0173(7) 0.0526(9) 0.0198(6) 0.0028(6) -0.0009(5) 0.0033(6) C15 0.0190(10) 0.0670(16) 0.0248(9) 0.0012(10) 0.0026(8) 0.0018(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C5 1.345(2) . ? O1 C4 1.4798(19) . ? O2 C5 1.219(2) . ? O3 C7 1.2311(19) . ? O4 C12 1.223(2) . ? O5 C14 1.196(2) . ? N1 C5 1.337(2) . ? N1 C6 1.445(2) . ? N1 H1 0.8600 . ? N2 C7 1.342(2) . ? N2 C11 1.459(2) . ? N2 C8 1.473(2) . ? N3 C12 1.341(2) . ? N3 C13 1.435(2) . ? N3 H3 0.8600 . ? C1 C4 1.520(3) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C4 1.520(3) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 C4 1.516(3) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C6 C7 1.518(2) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C8 C9 1.530(2) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.528(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.535(2) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.524(2) . ? C11 H11 0.9800 . ? C13 C14 1.509(2) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 O6 1.328(2) . ? O6 C15 1.445(2) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 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 C4 119.98(13) . . ? C5 N1 C6 120.77(14) . . ? C5 N1 H1 119.6 . . ? C6 N1 H1 119.6 . . ? C7 N2 C11 119.92(14) . . ? C7 N2 C8 127.12(14) . . ? C11 N2 C8 112.95(13) . . ? C12 N3 C13 122.01(14) . . ? C12 N3 H3 119.0 . . ? C13 N3 H3 119.0 . . ? C4 C1 H1A 109.5 . . ? C4 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C4 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C4 C2 H2A 109.5 . . ? C4 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C4 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C4 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? O1 C4 C3 109.95(14) . . ? O1 C4 C1 101.62(13) . . ? C3 C4 C1 110.80(15) . . ? O1 C4 C2 110.78(14) . . ? C3 C4 C2 112.51(16) . . ? C1 C4 C2 110.66(15) . . ? O2 C5 N1 124.07(16) . . ? O2 C5 O1 125.37(15) . . ? N1 C5 O1 110.55(14) . . ? N1 C6 C7 109.42(13) . . ? N1 C6 H6A 109.8 . . ? C7 C6 H6A 109.8 . . ? N1 C6 H6B 109.8 . . ? C7 C6 H6B 109.8 . . ? H6A C6 H6B 108.2 . . ? O3 C7 N2 122.31(15) . . ? O3 C7 C6 122.36(15) . . ? N2 C7 C6 115.31(14) . . ? N2 C8 C9 103.71(13) . . ? N2 C8 H8A 111.0 . . ? C9 C8 H8A 111.0 . . ? N2 C8 H8B 111.0 . . ? C9 C8 H8B 111.0 . . ? H8A C8 H8B 109.0 . . ? C10 C9 C8 103.64(14) . . ? C10 C9 H9A 111.0 . . ? C8 C9 H9A 111.0 . . ? C10 C9 H9B 111.0 . . ? C8 C9 H9B 111.0 . . ? H9A C9 H9B 109.0 . . ? C9 C10 C11 104.30(14) . . ? C9 C10 H10A 110.9 . . ? C11 C10 H10A 110.9 . . ? C9 C10 H10B 110.9 . . ? C11 C10 H10B 110.9 . . ? H10A C10 H10B 108.9 . . ? N2 C11 C12 111.32(13) . . ? N2 C11 C10 102.99(13) . . ? C12 C11 C10 109.86(13) . . ? N2 C11 H11 110.8 . . ? C12 C11 H11 110.8 . . ? C10 C11 H11 110.8 . . ? O4 C12 N3 123.09(15) . . ? O4 C12 C11 122.57(15) . . ? N3 C12 C11 114.22(14) . . ? N3 C13 C14 116.28(14) . . ? N3 C13 H13A 108.2 . . ? C14 C13 H13A 108.2 . . ? N3 C13 H13B 108.2 . . ? C14 C13 H13B 108.2 . . ? H13A C13 H13B 107.4 . . ? O5 C14 O6 123.17(16) . . ? O5 C14 C13 122.74(16) . . ? O6 C14 C13 114.09(14) . . ? C14 O6 C15 114.84(14) . . ? O6 C15 H15A 109.5 . . ? O6 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O6 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 O1 C4 C3 57.3(2) . . . . ? C5 O1 C4 C1 174.70(14) . . . . ? C5 O1 C4 C2 -67.70(19) . . . . ? C6 N1 C5 O2 -0.9(3) . . . . ? C6 N1 C5 O1 -179.61(13) . . . . ? C4 O1 C5 O2 14.4(2) . . . . ? C4 O1 C5 N1 -166.95(14) . . . . ? C5 N1 C6 C7 164.12(15) . . . . ? C11 N2 C7 O3 -0.5(2) . . . . ? C8 N2 C7 O3 -179.46(16) . . . . ? C11 N2 C7 C6 -179.51(14) . . . . ? C8 N2 C7 C6 1.6(2) . . . . ? N1 C6 C7 O3 -1.6(2) . . . . ? N1 C6 C7 N2 177.40(14) . . . . ? C7 N2 C8 C9 170.06(15) . . . . ? C11 N2 C8 C9 -8.91(18) . . . . ? N2 C8 C9 C10 27.23(17) . . . . ? C8 C9 C10 C11 -35.63(17) . . . . ? C7 N2 C11 C12 -74.47(18) . . . . ? C8 N2 C11 C12 104.59(16) . . . . ? C7 N2 C11 C10 167.87(14) . . . . ? C8 N2 C11 C10 -13.07(17) . . . . ? C9 C10 C11 N2 29.81(16) . . . . ? C9 C10 C11 C12 -88.87(16) . . . . ? C13 N3 C12 O4 -2.9(3) . . . . ? C13 N3 C12 C11 173.16(14) . . . . ? N2 C11 C12 O4 -37.4(2) . . . . ? C10 C11 C12 O4 76.0(2) . . . . ? N2 C11 C12 N3 146.45(14) . . . . ? C10 C11 C12 N3 -100.13(17) . . . . ? C12 N3 C13 C14 -103.75(19) . . . . ? N3 C13 C14 O5 -173.15(19) . . . . ? N3 C13 C14 O6 7.5(2) . . . . ? O5 C14 O6 C15 0.6(3) . . . . ? C13 C14 O6 C15 179.91(17) . . . . ? 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 H1 O4 0.86 2.28 2.8433(19) 122.7 4_656 N3 H3 O2 0.86 1.95 2.7666(19) 158.5 4_656 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.324 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.053