# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Dr Animesh Pramanik' _publ_contact_author_address ; Chemistry University of Calcutta 92, A. P. C. Road, Kolkata-700009 Kolkata India Kolkata-700 009 ; _publ_contact_author_email 'ANIMESH IN2001@YAHOO.CO.IN' _publ_section_title ; Remarkable fibrillation through b-sheet mediated self-assembly of dipeptides of w-amino acids ; loop_ _publ_author_name 'Animesh Pramanik' 'Michael G.B. Drew' 'Anita Dutt' data_Peptide_I _database_code_depnum_ccdc_archive 'CCDC 263795' _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety (Boc-?-Ala-mABA-OMe) _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C16 H22 N2 O5' _chemical_formula_weight 322.36 _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' 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 5.108(7) _cell_length_b 5.710(7) _cell_length_c 14.903(16) _cell_angle_alpha 79.659(10) _cell_angle_beta 81.128(10) _cell_angle_gamma 89.620(10) _cell_volume 422.4(9) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour white _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_method ? _exptl_crystal_F_000 172 _exptl_absorpt_coefficient_mu 0.095 _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_standards_interval_count ? _diffrn_measurement_device 'Marresearch Image Plate' _diffrn_measurement_method '95 frames at 2^o intervals, counting time 2 min.' _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2247 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0426 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 25.67 _reflns_number_total 2247 _reflns_number_observed 1886 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'XDS (Kabsch, 1991)' _computing_cell_refinement XDS _computing_data_reduction XDS _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics PLATON(Spek,1994) _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 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^)+(0.0594P)^2^+0.0631P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0626(118) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(153) _refine_ls_number_reflns 2246 _refine_ls_number_parameters 213 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0670 _refine_ls_R_factor_obs 0.0520 _refine_ls_wR_factor_all 0.1329 _refine_ls_wR_factor_obs 0.1146 _refine_ls_goodness_of_fit_all 1.109 _refine_ls_goodness_of_fit_obs 1.165 _refine_ls_restrained_S_all 1.226 _refine_ls_restrained_S_obs 1.164 _refine_ls_shift/esd_max 0.013 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.5233(4) -0.9542(4) 0.6413(2) 0.0474(7) Uani 1 d . . C101 C 0.6799(6) -1.0978(6) 0.7068(2) 0.0381(8) Uani 1 d . . C102 C 0.4726(9) -1.2629(10) 0.7719(3) 0.0784(15) Uani 1 d . . H10A H 0.3407(33) -1.1697(10) 0.8016(15) 0.094 Uiso 1 calc R . H10B H 0.5562(13) -1.3630(39) 0.8177(13) 0.094 Uiso 1 calc R . H10C H 0.3903(43) -1.3599(38) 0.7373(5) 0.094 Uiso 1 calc R . C103 C 0.8801(8) -1.2432(7) 0.6569(3) 0.0534(10) Uani 1 d . . H10D H 0.9471(35) -1.3631(27) 0.7010(3) 0.064 Uiso 1 calc R . H10E H 1.0237(24) -1.1414(9) 0.6225(13) 0.064 Uiso 1 calc R . H10F H 0.7973(14) -1.3180(35) 0.6154(12) 0.064 Uiso 1 calc R . C104 C 0.8046(9) -0.9345(7) 0.7589(3) 0.0595(11) Uani 1 d . . H10G H 0.9465(35) -0.8429(34) 0.7183(6) 0.071 Uiso 1 calc R . H10H H 0.8729(47) -1.0282(8) 0.8100(11) 0.071 Uiso 1 calc R . H10I H 0.6734(15) -0.8291(32) 0.7814(16) 0.071 Uiso 1 calc R . C2 C 0.6455(6) -0.7923(6) 0.5704(2) 0.0330(7) Uani 1 d . . O2 O 0.8829(4) -0.7549(5) 0.5505(2) 0.0487(6) Uani 1 d . . N3 N 0.4635(5) -0.6702(5) 0.5249(2) 0.0428(7) Uani 1 d . . H3 H 0.2977(5) -0.6992(5) 0.5450(2) 0.051 Uiso 1 calc R . C4 C 0.5427(7) -0.4903(6) 0.4425(2) 0.0404(8) Uani 1 d . . H4A H 0.5314(7) -0.5590(6) 0.3882(2) 0.048 Uiso 1 calc R . H4B H 0.7259(7) -0.4425(6) 0.4401(2) 0.048 Uiso 1 calc R . C5 C 0.3737(7) -0.2752(6) 0.4405(2) 0.0454(9) Uani 1 d . . H5A H 0.3678(7) -0.2168(6) 0.4980(2) 0.054 Uiso 1 calc R . H5B H 0.1943(7) -0.3187(6) 0.4351(2) 0.054 Uiso 1 calc R . C6 C 0.4804(6) -0.0795(6) 0.3604(2) 0.0349(7) Uani 1 d . . O6 O 0.7195(4) -0.0386(5) 0.3375(2) 0.0550(7) Uani 1 d . . N7 N 0.2950(5) 0.0506(5) 0.3180(2) 0.0390(7) Uani 1 d . . H7 H 0.1313(5) 0.0116(5) 0.3381(2) 0.047 Uiso 1 calc R . C8 C 0.3495(6) 0.2459(5) 0.2430(2) 0.0331(7) Uani 1 d . . C9 C 0.1835(7) 0.4385(7) 0.2400(3) 0.0492(9) Uani 1 d . . H9 H 0.0379(7) 0.4383(7) 0.2859(3) 0.059 Uiso 1 calc R . C10 C 0.2349(9) 0.6344(8) 0.1673(3) 0.0583(11) Uani 1 d . . H10 H 0.1223(9) 0.7633(8) 0.1652(3) 0.070 Uiso 1 calc R . C11 C 0.4497(8) 0.6369(7) 0.0997(3) 0.0541(10) Uani 1 d . . H11 H 0.4860(8) 0.7694(7) 0.0530(3) 0.065 Uiso 1 calc R . C12 C 0.6138(7) 0.4414(6) 0.1008(2) 0.0403(8) Uani 1 d . . C13 C 0.5639(6) 0.2456(6) 0.1728(2) 0.0356(7) Uani 1 d . . H13 H 0.6739(6) 0.1150(6) 0.1738(2) 0.043 Uiso 1 calc R . C14 C 0.8348(8) 0.4413(7) 0.0220(2) 0.0504(10) Uani 1 d . . O14 O 0.8974(7) 0.6085(6) -0.0389(2) 0.0836(10) Uani 1 d . . O15 O 0.9567(5) 0.2331(5) 0.0276(2) 0.0618(8) Uani 1 d . . C16 C 1.1720(9) 0.2126(10) -0.0470(3) 0.0708(13) Uani 1 d . . H16A H 1.2124(38) 0.0478(10) -0.0459(12) 0.085 Uiso 1 calc R . H16B H 1.3261(20) 0.2972(44) -0.0391(11) 0.085 Uiso 1 calc R . H16C H 1.1191(23) 0.2793(45) -0.1052(3) 0.085 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 O1 0.0241(14) 0.058(2) 0.0481(14) 0.0203(12) -0.0047(10) -0.0016(10) C101 0.027(2) 0.041(2) 0.040(2) 0.0086(15) -0.0081(13) 0.0041(14) C102 0.046(3) 0.088(4) 0.078(3) 0.046(3) -0.010(2) -0.001(2) C103 0.054(3) 0.041(2) 0.067(2) -0.014(2) -0.010(2) 0.003(2) C104 0.079(3) 0.056(3) 0.048(2) -0.007(2) -0.026(2) 0.022(2) C2 0.023(2) 0.038(2) 0.034(2) 0.0009(14) -0.0023(12) -0.0058(12) O2 0.0238(14) 0.060(2) 0.0531(14) 0.0115(12) -0.0019(10) -0.0092(10) N3 0.021(2) 0.054(2) 0.044(2) 0.0156(14) -0.0030(11) -0.0074(12) C4 0.040(2) 0.046(2) 0.030(2) 0.004(2) -0.0003(14) -0.003(2) C5 0.034(2) 0.051(2) 0.042(2) 0.007(2) 0.0056(15) -0.005(2) C6 0.023(2) 0.043(2) 0.033(2) 0.0043(14) 0.0022(12) -0.0043(13) O6 0.0254(15) 0.068(2) 0.056(2) 0.0263(13) -0.0025(10) -0.0086(11) N7 0.0224(15) 0.047(2) 0.0428(15) 0.0001(13) 0.0004(11) -0.0048(11) C8 0.030(2) 0.032(2) 0.039(2) -0.0056(14) -0.0107(13) 0.0004(13) C9 0.038(2) 0.053(3) 0.060(2) -0.012(2) -0.017(2) 0.009(2) C10 0.067(3) 0.040(2) 0.073(3) -0.009(2) -0.029(2) 0.018(2) C11 0.069(3) 0.039(2) 0.052(2) 0.007(2) -0.022(2) 0.002(2) C12 0.047(2) 0.036(2) 0.037(2) 0.005(2) -0.0160(14) -0.0071(15) C13 0.034(2) 0.032(2) 0.039(2) 0.0025(14) -0.0114(13) 0.0018(13) C14 0.054(2) 0.061(3) 0.033(2) 0.009(2) -0.015(2) -0.013(2) O14 0.094(3) 0.080(2) 0.055(2) 0.038(2) 0.000(2) -0.001(2) O15 0.072(2) 0.059(2) 0.0431(15) 0.0031(14) 0.0135(12) -0.0020(15) C16 0.072(3) 0.091(4) 0.042(2) -0.010(2) 0.013(2) -0.004(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 C2 1.347(4) . ? O1 C101 1.487(4) . ? C101 C103 1.505(5) . ? C101 C104 1.516(5) . ? C101 C102 1.523(5) . ? C2 O2 1.214(4) . ? C2 N3 1.351(4) . ? N3 C4 1.459(4) . ? C4 C5 1.495(5) . ? C5 C6 1.517(4) . ? C6 O6 1.229(4) . ? C6 N7 1.362(4) . ? N7 C8 1.425(4) . ? C8 C9 1.383(5) . ? C8 C13 1.394(5) . ? C9 C10 1.405(6) . ? C10 C11 1.369(6) . ? C11 C12 1.390(6) . ? C12 C13 1.398(5) . ? C12 C14 1.498(5) . ? C14 O14 1.200(5) . ? C14 O15 1.333(5) . ? O15 C16 1.459(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 C2 O1 C101 120.2(3) . . ? O1 C101 C103 110.7(3) . . ? O1 C101 C104 109.3(3) . . ? C103 C101 C104 112.9(3) . . ? O1 C101 C102 103.4(3) . . ? C103 C101 C102 109.5(4) . . ? C104 C101 C102 110.6(3) . . ? O2 C2 O1 125.9(3) . . ? O2 C2 N3 124.2(3) . . ? O1 C2 N3 109.9(3) . . ? C2 N3 C4 121.3(3) . . ? N3 C4 C5 112.4(3) . . ? C4 C5 C6 111.3(3) . . ? O6 C6 N7 122.7(3) . . ? O6 C6 C5 121.4(3) . . ? N7 C6 C5 115.8(3) . . ? C6 N7 C8 125.5(3) . . ? C9 C8 C13 119.6(3) . . ? C9 C8 N7 118.9(3) . . ? C13 C8 N7 121.5(3) . . ? C8 C9 C10 119.9(3) . . ? C11 C10 C9 120.4(4) . . ? C10 C11 C12 120.1(4) . . ? C11 C12 C13 119.8(3) . . ? C11 C12 C14 118.9(3) . . ? C13 C12 C14 121.3(3) . . ? C8 C13 C12 120.1(3) . . ? O14 C14 O15 123.5(4) . . ? O14 C14 C12 124.4(4) . . ? O15 C14 C12 112.0(3) . . ? C14 O15 C16 116.4(3) . . ? 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 C2 O1 C101 C103 -60.2(4) . . . . ? C2 O1 C101 C104 64.8(4) . . . . ? C2 O1 C101 C102 -177.4(3) . . . . ? C101 O1 C2 O2 3.4(5) . . . . ? C101 O1 C2 N3 -174.9(3) . . . . ? O2 C2 N3 C4 4.3(5) . . . . ? O1 C2 N3 C4 -177.4(3) . . . . ? C2 N3 C4 C5 -139.2(3) . . . . ? N3 C4 C5 C6 173.1(3) . . . . ? C4 C5 C6 O6 -39.1(4) . . . . ? C4 C5 C6 N7 142.8(3) . . . . ? O6 C6 N7 C8 0.3(5) . . . . ? C5 C6 N7 C8 178.4(3) . . . . ? C6 N7 C8 C9 -142.7(3) . . . . ? C6 N7 C8 C13 37.9(4) . . . . ? C13 C8 C9 C10 -1.4(5) . . . . ? N7 C8 C9 C10 179.2(3) . . . . ? C8 C9 C10 C11 -0.4(5) . . . . ? C9 C10 C11 C12 2.2(6) . . . . ? C10 C11 C12 C13 -2.1(5) . . . . ? C10 C11 C12 C14 175.3(4) . . . . ? C9 C8 C13 C12 1.4(4) . . . . ? N7 C8 C13 C12 -179.2(3) . . . . ? C11 C12 C13 C8 0.3(4) . . . . ? C14 C12 C13 C8 -177.0(3) . . . . ? C11 C12 C14 O14 7.2(5) . . . . ? C13 C12 C14 O14 -175.5(4) . . . . ? C11 C12 C14 O15 -173.3(3) . . . . ? C13 C12 C14 O15 4.0(4) . . . . ? O14 C14 O15 C16 -1.7(6) . . . . ? C12 C14 O15 C16 178.8(3) . . . . ? _refine_diff_density_max 0.131 _refine_diff_density_min -0.139 _refine_diff_density_rms 0.032 data_Peptide_II _database_code_depnum_ccdc_archive 'CCDC 263796' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety (Boc-??Abu-mABA-OMe) _chemical_formula_sum 'C17 H24 N2 O5' _chemical_formula_weight 336.38 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.448(6) _cell_length_b 11.674(12) _cell_length_c 14.810(14) _cell_angle_alpha 79.936(10) _cell_angle_beta 79.890(10) _cell_angle_gamma 85.346(10) _cell_volume 911.8(16) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour white _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.225 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_standards_number ? _diffrn_measurement_device 'Marresearch Image Plate' _diffrn_measurement_method '95 frames at 2^o intervals, counting time 2 min.' _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5224 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.1475 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.42 _diffrn_reflns_theta_max 26.35 _reflns_number_total 3040 _reflns_number_gt 1305 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XDS (Kabsch, 1991)' _computing_cell_refinement XDS _computing_data_reduction XDS _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics PLATON(Spek,1994) _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 ; w=1/[\s^2^(Fo^2^)+(0.1205P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.051(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3040 _refine_ls_number_parameters 222 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1709 _refine_ls_R_factor_gt 0.0931 _refine_ls_wR_factor_ref 0.2686 _refine_ls_wR_factor_gt 0.2465 _refine_ls_goodness_of_fit_ref 0.988 _refine_ls_restrained_S_all 0.988 _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 0.6949(10) 0.2651(5) 0.0132(4) 0.0439(14) Uani 1 1 d . . . C2 C 0.7041(10) 0.3693(5) 0.0502(4) 0.0456(14) Uani 1 1 d . . . H2 H 0.8421 0.4145 0.0295 0.055 Uiso 1 1 calc R . . C3 C 0.5164(9) 0.4049(4) 0.1151(4) 0.0406(13) Uani 1 1 d . . . C4 C 0.3109(10) 0.3389(4) 0.1468(4) 0.0442(14) Uani 1 1 d . . . H4 H 0.1804 0.3633 0.1899 0.053 Uiso 1 1 calc R . . C5 C 0.3009(11) 0.2369(5) 0.1142(4) 0.0574(17) Uani 1 1 d . . . H5 H 0.1632 0.1922 0.1379 0.069 Uiso 1 1 calc R . . C6 C 0.4777(10) 0.1974(5) 0.0499(4) 0.0475(15) Uani 1 1 d . . . H6 H 0.4609 0.1280 0.0294 0.057 Uiso 1 1 calc R . . N11 N 0.8980(8) 0.2295(4) -0.0523(3) 0.0481(12) Uani 1 1 d . . . H11 H 1.0161 0.2773 -0.0672 0.058 Uiso 1 1 calc R . . C12 C 0.9422(12) 0.1345(5) -0.0960(4) 0.0559(16) Uani 1 1 d . . . C13 C 1.1677(11) 0.1302(5) -0.1625(4) 0.0611(17) Uani 1 1 d . . . H13A H 1.3082 0.1373 -0.1320 0.073 Uiso 1 1 calc R . . H13B H 1.1631 0.1968 -0.2116 0.073 Uiso 1 1 calc R . . C15 C 1.2130(10) 0.0169(5) -0.2072(4) 0.0450(14) Uani 1 1 d . . . H15A H 1.2137 -0.0505 -0.1585 0.054 Uiso 1 1 calc R . . H15B H 1.0778 0.0108 -0.2406 0.054 Uiso 1 1 calc R . . O14 O 0.7848(7) 0.0553(4) -0.0786(3) 0.0629(12) Uani 1 1 d . . . C31 C 0.5549(11) 0.5158(5) 0.1491(4) 0.0466(14) Uani 1 1 d . . . C16 C 1.4656(10) 0.0176(5) -0.2752(4) 0.0490(15) Uani 1 1 d . . . H16A H 1.5976 0.0351 -0.2443 0.059 Uiso 1 1 calc R . . H16B H 1.5046 -0.0590 -0.2925 0.059 Uiso 1 1 calc R . . O32 O 0.3491(8) 0.5394(4) 0.2134(3) 0.0689(13) Uani 1 1 d . . . N17 N 1.4549(9) 0.1036(4) -0.3584(3) 0.0552(13) Uani 1 1 d . . . H17 H 1.3126 0.1254 -0.3751 0.066 Uiso 1 1 calc R . . C33 C 0.3768(15) 0.6399(7) 0.2621(6) 0.096(3) Uani 1 1 d . . . H33A H 0.5444 0.6652 0.2448 0.116 Uiso 1 1 calc R . . H33B H 0.3419 0.6152 0.3282 0.116 Uiso 1 1 calc R . . H33C H 0.2618 0.7031 0.2444 0.116 Uiso 1 1 calc R . . C18 C 1.6675(14) 0.1506(5) -0.4110(5) 0.0590(17) Uani 1 1 d . . . O19 O 1.8711(9) 0.1344(4) -0.3891(3) 0.0663(13) Uani 1 1 d . . . O34 O 0.7280(8) 0.5750(4) 0.1291(3) 0.0641(12) Uani 1 1 d . . . O20 O 1.6163(7) 0.2185(3) -0.4897(3) 0.0598(12) Uani 1 1 d . . . C21 C 1.8153(11) 0.2700(5) -0.5630(4) 0.0494(14) Uani 1 1 d . . . C22 C 1.6765(14) 0.3303(7) -0.6369(6) 0.101(3) Uani 1 1 d . . . H22A H 1.5185 0.3615 -0.6090 0.121 Uiso 1 1 calc R . . H22B H 1.6494 0.2758 -0.6754 0.121 Uiso 1 1 calc R . . H22C H 1.7717 0.3924 -0.6742 0.121 Uiso 1 1 calc R . . C23 C 2.0020(13) 0.1763(6) -0.5950(5) 0.081(2) Uani 1 1 d . . . H23A H 2.1397 0.2119 -0.6373 0.097 Uiso 1 1 calc R . . H23B H 1.9229 0.1273 -0.6259 0.097 Uiso 1 1 calc R . . H23C H 2.0619 0.1301 -0.5422 0.097 Uiso 1 1 calc R . . C24 C 1.9481(14) 0.3545(6) -0.5266(5) 0.087(2) Uani 1 1 d . . . H24A H 1.8289 0.4103 -0.5009 0.104 Uiso 1 1 calc R . . H24B H 2.0642 0.3941 -0.5763 0.104 Uiso 1 1 calc R . . H24C H 2.0367 0.3134 -0.4791 0.104 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 C1 0.042(3) 0.040(3) 0.051(4) -0.009(3) -0.007(3) -0.004(2) C2 0.049(4) 0.040(3) 0.049(4) -0.009(3) -0.007(3) -0.005(2) C3 0.037(3) 0.035(3) 0.048(3) -0.001(3) -0.007(3) -0.004(2) C4 0.043(3) 0.040(3) 0.049(4) -0.006(3) -0.009(3) -0.003(2) C5 0.053(4) 0.054(4) 0.065(4) -0.012(3) -0.005(3) -0.007(3) C6 0.046(4) 0.040(3) 0.058(4) -0.008(3) -0.011(3) -0.011(3) N11 0.047(3) 0.044(3) 0.056(3) -0.009(2) -0.011(2) -0.007(2) C12 0.064(4) 0.045(4) 0.059(4) -0.012(3) -0.010(3) -0.001(3) C13 0.057(4) 0.062(4) 0.066(4) -0.009(3) -0.015(3) -0.008(3) C15 0.051(4) 0.038(3) 0.045(3) -0.005(3) -0.006(3) -0.007(2) O14 0.062(3) 0.054(3) 0.076(3) -0.017(2) -0.008(2) -0.015(2) C31 0.045(4) 0.045(4) 0.048(4) -0.006(3) -0.006(3) -0.002(3) C16 0.050(4) 0.039(3) 0.057(4) -0.008(3) -0.005(3) -0.003(2) O32 0.074(3) 0.062(3) 0.072(3) -0.018(2) -0.006(2) -0.006(2) N17 0.051(3) 0.057(3) 0.057(3) -0.007(3) -0.009(2) -0.002(2) C33 0.109(6) 0.087(6) 0.090(6) -0.023(5) 0.006(5) -0.016(5) C18 0.065(5) 0.054(4) 0.060(4) -0.015(3) -0.011(4) -0.004(3) O19 0.062(3) 0.067(3) 0.070(3) -0.006(2) -0.016(2) -0.004(2) O34 0.062(3) 0.056(3) 0.073(3) -0.010(2) -0.003(2) -0.013(2) O20 0.051(3) 0.061(3) 0.064(3) -0.004(2) -0.008(2) -0.0019(19) C21 0.048(3) 0.046(3) 0.054(4) -0.005(3) -0.008(3) -0.004(3) C22 0.084(6) 0.119(7) 0.091(6) 0.005(5) -0.013(5) -0.007(5) C23 0.074(5) 0.092(6) 0.074(5) -0.008(4) -0.013(4) -0.002(4) C24 0.085(5) 0.088(6) 0.088(6) -0.008(4) -0.011(4) -0.021(4) _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 N11 1.423(7) . ? C1 C2 1.427(7) . ? C1 C6 1.448(7) . ? C2 C3 1.367(8) . ? C3 C4 1.377(7) . ? C3 C31 1.510(8) . ? C4 C5 1.370(8) . ? C5 C6 1.344(8) . ? N11 C12 1.364(7) . ? C12 O14 1.275(7) . ? C12 C13 1.436(8) . ? C13 C15 1.564(8) . ? C15 C16 1.556(7) . ? C31 O34 1.180(6) . ? C31 O32 1.381(7) . ? C16 N17 1.453(7) . ? O32 C33 1.511(8) . ? N17 C18 1.374(8) . ? C18 O19 1.201(7) . ? C18 O20 1.349(7) . ? O20 C21 1.476(7) . ? C21 C22 1.484(9) . ? C21 C24 1.492(9) . ? C21 C23 1.513(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 N11 C1 C2 120.2(5) . . ? N11 C1 C6 123.5(5) . . ? C2 C1 C6 116.2(5) . . ? C3 C2 C1 122.1(5) . . ? C2 C3 C4 119.7(5) . . ? C2 C3 C31 116.0(5) . . ? C4 C3 C31 124.2(5) . . ? C5 C4 C3 119.2(5) . . ? C6 C5 C4 124.0(6) . . ? C5 C6 C1 118.7(5) . . ? C12 N11 C1 132.7(5) . . ? O14 C12 N11 120.2(6) . . ? O14 C12 C13 122.7(6) . . ? N11 C12 C13 117.1(5) . . ? C12 C13 C15 114.6(5) . . ? C16 C15 C13 111.1(4) . . ? O34 C31 O32 122.4(6) . . ? O34 C31 C3 129.0(6) . . ? O32 C31 C3 108.6(5) . . ? N17 C16 C15 111.1(4) . . ? C31 O32 C33 114.1(5) . . ? C18 N17 C16 121.3(5) . . ? O19 C18 O20 124.7(6) . . ? O19 C18 N17 124.3(6) . . ? O20 C18 N17 111.0(6) . . ? C18 O20 C21 121.9(5) . . ? O20 C21 C22 103.3(5) . . ? O20 C21 C24 109.9(5) . . ? C22 C21 C24 111.1(6) . . ? O20 C21 C23 110.6(5) . . ? C22 C21 C23 112.9(6) . . ? C24 C21 C23 108.9(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 N11 C1 C2 C3 -178.1(5) . . . . ? C6 C1 C2 C3 -1.4(8) . . . . ? C1 C2 C3 C4 0.2(8) . . . . ? C1 C2 C3 C31 178.9(5) . . . . ? C2 C3 C4 C5 1.5(8) . . . . ? C31 C3 C4 C5 -177.0(5) . . . . ? C3 C4 C5 C6 -2.1(9) . . . . ? C4 C5 C6 C1 0.9(9) . . . . ? N11 C1 C6 C5 177.5(5) . . . . ? C2 C1 C6 C5 0.8(8) . . . . ? C2 C1 N11 C12 177.8(5) . . . . ? C6 C1 N11 C12 1.3(9) . . . . ? C1 N11 C12 O14 -1.7(10) . . . . ? C1 N11 C12 C13 177.1(6) . . . . ? O14 C12 C13 C15 -3.6(9) . . . . ? N11 C12 C13 C15 177.6(5) . . . . ? C12 C13 C15 C16 -177.8(5) . . . . ? C2 C3 C31 O34 -2.1(9) . . . . ? C4 C3 C31 O34 176.5(6) . . . . ? C2 C3 C31 O32 179.6(5) . . . . ? C4 C3 C31 O32 -1.7(7) . . . . ? C13 C15 C16 N17 -70.1(6) . . . . ? O34 C31 O32 C33 -5.7(8) . . . . ? C3 C31 O32 C33 172.7(5) . . . . ? C15 C16 N17 C18 155.8(5) . . . . ? C16 N17 C18 O19 -7.4(9) . . . . ? C16 N17 C18 O20 173.4(5) . . . . ? O19 C18 O20 C21 7.0(9) . . . . ? N17 C18 O20 C21 -173.7(5) . . . . ? C18 O20 C21 C22 176.8(6) . . . . ? C18 O20 C21 C24 -64.6(7) . . . . ? C18 O20 C21 C23 55.7(7) . . . . ? _diffrn_measured_fraction_theta_max 0.820 _diffrn_reflns_theta_full 26.35 _diffrn_measured_fraction_theta_full 0.820 _refine_diff_density_max 0.262 _refine_diff_density_min -0.284 _refine_diff_density_rms 0.064