# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_publication_text _journal_name_full Org.Biomol.Chem. #TrackingRef 'Ala-Val-ol.gus' _journal_coden_Cambridge 0177 _publ_contact_author_name 'Hosahudya N. Gopi' _publ_contact_author_address ;Department of Chemistry Indian Institute of Science Education and Research Garware Circle, Pashan Pune-411021 India ; _publ_contact_author_email hn.gopi@iiserpune.ac.in _publ_contact_author_phone 91(20)25908075 _publ_contact_author_fax 91(20)25899790 loop_ _publ_author_name _publ_author_address 'G.Hosahudya ' ;Department of Chemistry Indian Institute of Science Education and Research Garware Circle, Pashan Pune-411021 India ; S.Jadhav ;Department of Chemistry Indian Institute of Science Education and Research Garware Circle, Pashan Pune-411021 India ; A.Bandyopadhyay ;Department of Chemistry Indian Institute of Science Education and Research Garware Circle, Pashan Pune-411021 India ; S.Benke ;Department of Chemistry Indian Institute of Science Education and Research Garware Circle, Pashan Pune-411021 India ; S.Mali ;Department of Chemistry Indian Institute of Science Education and Research Garware Circle, Pashan Pune-411021 India ; # Attachment 'SVJ1-FVOL.cif' data_svj1 _database_code_depnum_ccdc_archive 'CCDC 794215' _audit_creation_method SHELXL-97 _chemical_name_systematic Fmoc-Val-CH2OH _chemical_name_common Fmoc-Val-CH2OH _chemical_formula_moiety 'C20 H23 N O3' _chemical_formula_sum 'C20 H23 N O3' _chemical_compound_source synthesis _exptl_crystal_recrystallization_method MeOH _chemical_melting_point 394(1) _exptl_crystal_description 'rod shape' _exptl_crystal_colour Colourless _diffrn_ambient_temperature 296(2) _diffrn_ambient_pressure '101.325 ' _chemical_formula_weight 325.39 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 4.942(4) _cell_length_b 11.622(11) _cell_length_c 15.783(14) _cell_angle_alpha 90.00 _cell_angle_beta 93.573(14) _cell_angle_gamma 90.00 _cell_volume 904.7(14) _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 ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.195 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 9389 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_av_sigmaI/netI 0.0383 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4239 _reflns_number_gt 2760 _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^)+(0.0000P)^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 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(8) _refine_ls_number_reflns 4239 _refine_ls_number_parameters 220 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0758 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.0548 _refine_ls_wR_factor_gt 0.0508 _refine_ls_goodness_of_fit_ref 1.456 _refine_ls_restrained_S_all 1.456 _refine_ls_shift/su_max 0.097 _refine_ls_shift/su_mean 0.009 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 0.9182(3) 0.46288(14) 0.59694(10) 0.0500(5) Uani 1 1 d . . . H1 H 0.7312 0.4557 0.5730 0.060 Uiso 1 1 calc R . . C2 C 0.9430(3) 0.56126(15) 0.65902(10) 0.0496(4) Uani 1 1 d . . . C3 C 0.8118(3) 0.57898(19) 0.73282(12) 0.0683(5) Uani 1 1 d . . . H3 H 0.6829 0.5269 0.7498 0.082 Uiso 1 1 calc R . . C4 C 0.8766(4) 0.6760(2) 0.78087(12) 0.0821(6) Uani 1 1 d . . . H4 H 0.7876 0.6896 0.8301 0.099 Uiso 1 1 calc R . . C5 C 1.0689(4) 0.75209(19) 0.75727(14) 0.0831(7) Uani 1 1 d . . . H5 H 1.1128 0.8154 0.7915 0.100 Uiso 1 1 calc R . . C6 C 1.1986(3) 0.73606(17) 0.68329(14) 0.0693(5) Uani 1 1 d . . . H6 H 1.3276 0.7884 0.6669 0.083 Uiso 1 1 calc R . . C7 C 1.1327(3) 0.64040(15) 0.63398(11) 0.0522(5) Uani 1 1 d . . . C8 C 1.2300(3) 0.60328(15) 0.55311(11) 0.0514(4) Uani 1 1 d . . . C9 C 1.4141(3) 0.65396(18) 0.50185(13) 0.0721(6) Uani 1 1 d . . . H9 H 1.5009 0.7223 0.5178 0.087 Uiso 1 1 calc R . . C10 C 1.4651(4) 0.6004(2) 0.42661(14) 0.0802(6) Uani 1 1 d . . . H10 H 1.5872 0.6334 0.3912 0.096 Uiso 1 1 calc R . . C11 C 1.3390(4) 0.4992(2) 0.40294(12) 0.0787(6) Uani 1 1 d . . . H11 H 1.3758 0.4648 0.3517 0.094 Uiso 1 1 calc R . . C12 C 1.1569(3) 0.44764(18) 0.45469(12) 0.0687(5) Uani 1 1 d . . . H12 H 1.0731 0.3786 0.4389 0.082 Uiso 1 1 calc R . . C13 C 1.1027(3) 0.50063(16) 0.52985(10) 0.0498(4) Uani 1 1 d . . . C14 C 1.0175(3) 0.34977(14) 0.63449(10) 0.0554(5) Uani 1 1 d . . . H14A H 1.0241 0.2921 0.5903 0.066 Uiso 1 1 calc R . . H14B H 1.1985 0.3588 0.6612 0.066 Uiso 1 1 calc R . . C15 C 0.9282(3) 0.23880(15) 0.75545(10) 0.0496(4) Uani 1 1 d . . . C16 C 0.7823(3) 0.12876(15) 0.87748(10) 0.0505(5) Uani 1 1 d . . . H16 H 0.9784 0.1241 0.8906 0.061 Uiso 1 1 calc R . . C17 C 0.6567(3) 0.17525(18) 0.95598(12) 0.0709(6) Uani 1 1 d . . . H17 H 0.4642 0.1904 0.9415 0.085 Uiso 1 1 calc R . . C18 C 0.6780(4) 0.0881(2) 1.02822(12) 0.1101(8) Uani 1 1 d . . . H18A H 0.8639 0.0658 1.0390 0.165 Uiso 1 1 calc R . . H18B H 0.5709 0.0216 1.0127 0.165 Uiso 1 1 calc R . . H18C H 0.6125 0.1222 1.0785 0.165 Uiso 1 1 calc R . . C19 C 0.7914(5) 0.2879(2) 0.98418(14) 0.1131(8) Uani 1 1 d . . . H19A H 0.7754 0.3424 0.9384 0.170 Uiso 1 1 calc R . . H19B H 0.9796 0.2744 0.9998 0.170 Uiso 1 1 calc R . . H19C H 0.7041 0.3180 1.0321 0.170 Uiso 1 1 calc R . . C20 C 0.6874(3) 0.01056(16) 0.85019(11) 0.0628(5) Uani 1 1 d . . . H20A H 0.7691 -0.0094 0.7978 0.075 Uiso 1 1 calc R . . H20B H 0.7504 -0.0447 0.8931 0.075 Uiso 1 1 calc R . . N1 N 0.7381(2) 0.21004(12) 0.80771(8) 0.0563(4) Uani 1 1 d . . . H1A H 0.5806 0.2411 0.7999 0.068 Uiso 1 1 calc R . . O1 O 0.83160(18) 0.31451(10) 0.69671(7) 0.0572(3) Uani 1 1 d . . . O2 O 1.16121(18) 0.20355(10) 0.75997(7) 0.0650(4) Uani 1 1 d . . . O3 O 0.3992(2) 0.00119(11) 0.83721(8) 0.0801(4) Uani 1 1 d . . . H3A H 0.3419 0.0532 0.8059 0.120 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 0.0449(8) 0.0465(12) 0.0575(11) 0.0074(10) -0.0048(8) -0.0032(8) C2 0.0487(9) 0.0485(12) 0.0506(11) 0.0028(10) -0.0039(8) 0.0056(8) C3 0.0642(10) 0.0710(16) 0.0695(14) 0.0042(13) 0.0023(10) 0.0028(11) C4 0.0881(13) 0.0872(19) 0.0709(14) -0.0117(14) 0.0031(11) 0.0177(14) C5 0.0933(16) 0.0659(17) 0.0869(17) -0.0184(14) -0.0207(13) 0.0125(13) C6 0.0666(11) 0.0526(14) 0.0865(15) 0.0011(13) -0.0124(11) -0.0019(10) C7 0.0517(9) 0.0422(12) 0.0613(12) 0.0068(10) -0.0096(8) 0.0029(9) C8 0.0458(8) 0.0477(12) 0.0600(12) 0.0150(10) -0.0019(8) 0.0028(9) C9 0.0647(10) 0.0673(15) 0.0840(15) 0.0259(13) 0.0010(10) -0.0013(10) C10 0.0740(12) 0.0917(19) 0.0759(16) 0.0335(15) 0.0130(11) 0.0172(14) C11 0.0859(13) 0.0950(19) 0.0554(12) 0.0098(15) 0.0048(11) 0.0274(14) C12 0.0742(12) 0.0715(15) 0.0591(13) 0.0024(12) -0.0067(10) 0.0087(11) C13 0.0477(9) 0.0509(12) 0.0498(11) 0.0070(10) -0.0067(8) 0.0046(9) C14 0.0472(8) 0.0525(13) 0.0667(12) 0.0123(10) 0.0055(8) -0.0031(8) C15 0.0403(8) 0.0502(12) 0.0573(11) 0.0037(10) -0.0037(7) -0.0039(8) C16 0.0365(7) 0.0599(13) 0.0549(11) 0.0045(10) 0.0019(7) 0.0024(8) C17 0.0581(9) 0.0881(17) 0.0671(13) -0.0120(13) 0.0086(9) 0.0015(11) C18 0.1353(16) 0.138(2) 0.0588(13) 0.0034(16) 0.0224(12) -0.0274(18) C19 0.1369(19) 0.096(2) 0.1057(19) -0.0397(16) 0.0033(14) 0.0088(17) C20 0.0621(10) 0.0612(13) 0.0642(12) 0.0053(11) -0.0023(8) 0.0119(10) N1 0.0331(6) 0.0637(11) 0.0722(10) 0.0203(9) 0.0045(6) 0.0059(7) O1 0.0399(6) 0.0542(8) 0.0774(8) 0.0218(7) 0.0034(5) 0.0007(6) O2 0.0339(5) 0.0811(10) 0.0801(8) 0.0256(7) 0.0047(5) 0.0076(6) O3 0.0672(7) 0.0618(10) 0.1091(11) 0.0143(8) -0.0127(6) -0.0123(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 C1 C13 1.505(2) . ? C1 C2 1.506(2) . ? C1 C14 1.511(2) . ? C2 C7 1.388(2) . ? C2 C3 1.383(2) . ? C3 C4 1.385(3) . ? C4 C5 1.367(3) . ? C5 C6 1.379(3) . ? C6 C7 1.384(2) . ? C7 C8 1.457(2) . ? C8 C9 1.386(2) . ? C8 C13 1.387(2) . ? C9 C10 1.378(3) . ? C10 C11 1.372(3) . ? C11 C12 1.388(2) . ? C12 C13 1.378(2) . ? C14 O1 1.4453(19) . ? C15 O2 1.2201(19) . ? C15 N1 1.3307(18) . ? C15 O1 1.3441(18) . ? C16 N1 1.457(2) . ? C16 C20 1.506(3) . ? C16 C17 1.519(2) . ? C17 C18 1.523(3) . ? C17 C19 1.523(3) . ? C20 O3 1.431(2) . ? 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 C13 C1 C2 102.02(14) . . ? C13 C1 C14 109.48(14) . . ? C2 C1 C14 113.21(14) . . ? C7 C2 C3 120.09(18) . . ? C7 C2 C1 110.28(15) . . ? C3 C2 C1 129.62(17) . . ? C2 C3 C4 118.53(19) . . ? C5 C4 C3 121.2(2) . . ? C4 C5 C6 120.7(2) . . ? C5 C6 C7 118.63(19) . . ? C6 C7 C2 120.76(18) . . ? C6 C7 C8 130.64(18) . . ? C2 C7 C8 108.60(16) . . ? C9 C8 C13 120.95(18) . . ? C9 C8 C7 130.55(18) . . ? C13 C8 C7 108.50(16) . . ? C10 C9 C8 118.2(2) . . ? C11 C10 C9 121.2(2) . . ? C10 C11 C12 120.7(2) . . ? C13 C12 C11 118.79(19) . . ? C12 C13 C8 120.19(17) . . ? C12 C13 C1 129.37(18) . . ? C8 C13 C1 110.43(16) . . ? O1 C14 C1 107.97(13) . . ? O2 C15 N1 125.42(16) . . ? O2 C15 O1 123.60(14) . . ? N1 C15 O1 110.97(14) . . ? N1 C16 C20 110.24(14) . . ? N1 C16 C17 109.65(16) . . ? C20 C16 C17 114.96(15) . . ? C18 C17 C16 111.19(18) . . ? C18 C17 C19 110.13(18) . . ? C16 C17 C19 110.54(16) . . ? O3 C20 C16 113.57(14) . . ? C15 N1 C16 123.57(13) . . ? C15 O1 C14 116.16(12) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.107 _refine_diff_density_min -0.161 _refine_diff_density_rms 0.028 # Attachment 'SVJ15.cif' data_svj15 _database_code_depnum_ccdc_archive 'CCDC 794216' _audit_creation_method SHELXL-97 _chemical_name_systematic Boc-Aib-Ala-Leu-CH2OH _chemical_name_common Boc-Aib-Ala-Leu-CH2OH _chemical_formula_moiety 'C18 H35 N3 O5' _chemical_formula_sum 'C19 H36 Cl3 N3 O5' _chemical_compound_source synthesis _exptl_crystal_recrystallization_method CHCl3 _chemical_melting_point 410(1) _exptl_crystal_description rectangular _exptl_crystal_colour Colourless _diffrn_ambient_temperature 296(2) _diffrn_ambient_pressure 101.325 _chemical_formula_weight 492.86 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' Cl Cl 0.1484 0.1585 '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 10.578(4) _cell_length_b 11.206(4) _cell_length_c 23.306(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2762.7(17) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.185 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 0.361 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 12526 _diffrn_reflns_av_R_equivalents 0.0992 _diffrn_reflns_av_sigmaI/netI 0.3083 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 3 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 28.28 _reflns_number_total 6526 _reflns_number_gt 1573 _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^)+(0.0883P)^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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.22(17) _refine_ls_number_reflns 6526 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2755 _refine_ls_R_factor_gt 0.0673 _refine_ls_wR_factor_ref 0.2113 _refine_ls_wR_factor_gt 0.1608 _refine_ls_goodness_of_fit_ref 0.715 _refine_ls_restrained_S_all 0.715 _refine_ls_shift/su_max 0.087 _refine_ls_shift/su_mean 0.006 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 0.2804(8) 0.6105(7) 0.3519(3) 0.127(3) Uani 1 1 d . . . H1A H 0.2654 0.6932 0.3602 0.190 Uiso 1 1 calc R . . H1B H 0.3211 0.5735 0.3841 0.190 Uiso 1 1 calc R . . H1C H 0.2013 0.5714 0.3446 0.190 Uiso 1 1 calc R . . C2 C 0.4865(6) 0.6734(6) 0.3042(3) 0.109(3) Uani 1 1 d . . . H2A H 0.4685 0.7503 0.3205 0.163 Uiso 1 1 calc R . . H2B H 0.5218 0.6834 0.2666 0.163 Uiso 1 1 calc R . . H2C H 0.5460 0.6321 0.3282 0.163 Uiso 1 1 calc R . . C3 C 0.3963(7) 0.4728(6) 0.2849(3) 0.118(3) Uani 1 1 d . . . H3A H 0.4588 0.4433 0.3113 0.177 Uiso 1 1 calc R . . H3B H 0.4293 0.4699 0.2466 0.177 Uiso 1 1 calc R . . H3C H 0.3218 0.4242 0.2873 0.177 Uiso 1 1 calc R . . C4 C 0.3635(6) 0.6003(6) 0.3001(3) 0.0716(18) Uani 1 1 d . . . C5 C 0.2461(6) 0.7511(6) 0.2433(3) 0.0577(15) Uani 1 1 d . . . C6 C 0.1274(6) 0.8791(5) 0.1785(2) 0.0565(16) Uani 1 1 d . . . C7 C 0.2361(6) 0.9588(5) 0.1612(3) 0.0799(19) Uani 1 1 d . . . H7A H 0.2038 1.0343 0.1483 0.120 Uiso 1 1 calc R . . H7B H 0.2827 0.9217 0.1307 0.120 Uiso 1 1 calc R . . H7C H 0.2908 0.9711 0.1935 0.120 Uiso 1 1 calc R . . C8 C 0.0392(6) 0.8606(6) 0.1271(2) 0.0768(18) Uani 1 1 d . . . H8A H -0.0304 0.8107 0.1383 0.115 Uiso 1 1 calc R . . H8B H 0.0850 0.8230 0.0965 0.115 Uiso 1 1 calc R . . H8C H 0.0077 0.9364 0.1144 0.115 Uiso 1 1 calc R . . C9 C 0.0485(5) 0.9390(6) 0.2253(2) 0.0450(14) Uani 1 1 d . . . C10 C -0.0977(5) 0.9146(5) 0.3063(2) 0.0541(16) Uani 1 1 d . . . H10 H -0.1618 0.9654 0.2883 0.065 Uiso 1 1 calc R . . C11 C -0.1665(6) 0.8100(5) 0.3359(3) 0.0783(19) Uani 1 1 d . . . H11A H -0.2228 0.7726 0.3091 0.117 Uiso 1 1 calc R . . H11B H -0.2139 0.8395 0.3681 0.117 Uiso 1 1 calc R . . H11C H -0.1055 0.7527 0.3491 0.117 Uiso 1 1 calc R . . C12 C -0.0266(6) 0.9902(5) 0.3502(2) 0.0514(15) Uani 1 1 d . . . C13 C 0.1858(6) 1.0407(5) 0.3896(2) 0.0590(16) Uani 1 1 d . . . H13 H 0.1359 1.0996 0.4109 0.071 Uiso 1 1 calc R . . C14 C 0.2738(6) 1.1081(6) 0.3483(3) 0.082(2) Uani 1 1 d . . . H14A H 0.3302 1.1584 0.3704 0.098 Uiso 1 1 calc R . . H14B H 0.3252 1.0507 0.3276 0.098 Uiso 1 1 calc R . . C15 C 0.2603(6) 0.9700(6) 0.4315(3) 0.082(2) Uani 1 1 d . . . H15A H 0.3103 1.0256 0.4539 0.098 Uiso 1 1 calc R . . H15B H 0.3192 0.9211 0.4099 0.098 Uiso 1 1 calc R . . C16 C 0.1917(11) 0.8884(8) 0.4735(4) 0.129(3) Uani 1 1 d . . . H16 H 0.1486 0.8268 0.4509 0.155 Uiso 1 1 calc R . . C17 C 0.0895(11) 0.9575(11) 0.5070(3) 0.174(5) Uani 1 1 d . . . H17A H 0.0988 0.9421 0.5473 0.261 Uiso 1 1 calc R . . H17B H 0.0072 0.9320 0.4947 0.261 Uiso 1 1 calc R . . H17C H 0.0987 1.0415 0.5000 0.261 Uiso 1 1 calc R . . C18 C 0.2818(10) 0.8255(8) 0.5141(4) 0.187(5) Uani 1 1 d . . . H18A H 0.3277 0.8838 0.5359 0.280 Uiso 1 1 calc R . . H18B H 0.3401 0.7779 0.4923 0.280 Uiso 1 1 calc R . . H18C H 0.2346 0.7751 0.5396 0.280 Uiso 1 1 calc R . . C19 C 0.7010(7) 0.1008(7) 0.4657(4) 0.114(3) Uani 1 1 d . . . H19 H 0.7681 0.0795 0.4386 0.137 Uiso 1 1 calc R . . Cl1 Cl 0.7657(4) 0.1786(4) 0.52128(17) 0.272(2) Uani 1 1 d . . . Cl2 Cl 0.6344(4) -0.0240(3) 0.49040(14) 0.2126(16) Uani 1 1 d . . . Cl3 Cl 0.5977(4) 0.1927(4) 0.4326(2) 0.308(3) Uani 1 1 d . . . N1 N 0.1730(4) 0.7626(4) 0.19708(18) 0.0497(12) Uani 1 1 d . . . H1 H 0.1524 0.7001 0.1778 0.060 Uiso 1 1 calc R . . N2 N -0.0173(4) 0.8658(4) 0.26078(18) 0.0535(12) Uani 1 1 d . . . H2 H -0.0118 0.7898 0.2565 0.064 Uiso 1 1 calc R . . N3 N 0.0985(5) 0.9671(4) 0.35559(16) 0.0518(12) Uani 1 1 d . . . H3 H 0.1287 0.9058 0.3381 0.062 Uiso 1 1 calc R . . O1 O 0.2938(4) 0.6399(4) 0.24811(16) 0.0671(11) Uani 1 1 d . . . O2 O 0.2682(3) 0.8306(4) 0.27766(16) 0.0642(11) Uani 1 1 d . . . O3 O 0.0406(4) 1.0488(4) 0.22948(14) 0.0602(11) Uani 1 1 d . . . O4 O -0.0819(4) 1.0642(3) 0.37831(15) 0.0639(12) Uani 1 1 d . . . O5 O 0.2066(5) 1.1810(4) 0.30755(19) 0.0922(15) Uani 1 1 d . . . H5 H 0.1649 1.1381 0.2862 0.138 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 0.125(7) 0.173(8) 0.082(5) 0.056(5) -0.010(6) 0.008(6) C2 0.081(6) 0.083(5) 0.162(7) 0.001(5) -0.039(5) -0.003(5) C3 0.111(6) 0.065(5) 0.179(7) 0.019(5) -0.049(6) 0.011(5) C4 0.057(5) 0.070(5) 0.088(5) 0.025(4) -0.018(4) 0.005(4) C5 0.055(4) 0.055(4) 0.063(4) -0.010(4) 0.006(4) 0.003(4) C6 0.064(4) 0.057(4) 0.049(4) -0.001(3) 0.001(3) 0.004(4) C7 0.074(5) 0.067(4) 0.099(5) 0.001(4) 0.037(4) -0.009(4) C8 0.099(5) 0.086(5) 0.045(3) -0.012(3) -0.010(4) 0.013(4) C9 0.040(4) 0.051(4) 0.044(3) -0.001(3) -0.010(3) 0.001(3) C10 0.039(4) 0.068(4) 0.055(3) -0.006(3) 0.003(3) -0.002(3) C11 0.077(5) 0.073(4) 0.085(4) -0.010(4) 0.037(4) -0.024(4) C12 0.048(4) 0.060(4) 0.046(4) 0.007(3) 0.006(3) 0.000(4) C13 0.065(4) 0.062(4) 0.050(3) 0.004(3) -0.016(3) -0.006(4) C14 0.079(5) 0.082(5) 0.084(4) 0.001(4) -0.005(4) -0.007(4) C15 0.090(5) 0.091(5) 0.065(4) -0.007(4) -0.022(4) -0.004(4) C16 0.192(10) 0.108(7) 0.088(6) 0.014(6) -0.022(7) -0.013(7) C17 0.178(10) 0.254(13) 0.090(6) 0.049(8) 0.011(7) -0.034(10) C18 0.265(13) 0.165(9) 0.131(7) 0.065(7) -0.111(9) -0.059(9) C19 0.081(5) 0.113(7) 0.148(7) -0.006(6) 0.037(5) 0.005(5) Cl1 0.276(5) 0.313(5) 0.227(4) -0.127(4) 0.038(3) -0.047(4) Cl2 0.253(4) 0.138(2) 0.247(4) 0.021(2) 0.054(3) -0.011(3) Cl3 0.153(3) 0.317(5) 0.453(7) 0.202(5) 0.001(4) 0.016(3) N1 0.058(3) 0.046(3) 0.045(3) -0.006(2) -0.007(3) -0.002(3) N2 0.050(3) 0.051(3) 0.059(3) -0.002(3) 0.011(3) 0.002(3) N3 0.052(3) 0.056(3) 0.048(3) -0.006(2) -0.004(2) 0.005(3) O1 0.069(3) 0.061(3) 0.071(3) -0.002(2) -0.007(2) 0.006(2) O2 0.059(3) 0.071(3) 0.062(2) -0.012(2) -0.012(2) 0.006(2) O3 0.074(3) 0.053(3) 0.053(2) 0.005(2) 0.005(2) 0.009(2) O4 0.068(3) 0.063(3) 0.060(2) -0.013(2) 0.008(2) 0.009(2) O5 0.112(4) 0.073(3) 0.091(3) 0.025(3) -0.023(3) -0.013(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 C1 C4 1.498(9) . ? C2 C4 1.540(9) . ? C3 C4 1.513(8) . ? C4 O1 1.486(6) . ? C5 O2 1.221(6) . ? C5 N1 1.333(6) . ? C5 O1 1.349(6) . ? C6 N1 1.457(6) . ? C6 C7 1.511(7) . ? C6 C9 1.528(7) . ? C6 C8 1.533(7) . ? C9 O3 1.236(6) . ? C9 N2 1.358(6) . ? C10 N2 1.466(6) . ? C10 C12 1.525(7) . ? C10 C11 1.543(7) . ? C12 O4 1.209(6) . ? C12 N3 1.354(6) . ? C13 N3 1.470(6) . ? C13 C15 1.484(7) . ? C13 C14 1.538(7) . ? C14 O5 1.440(6) . ? C15 C16 1.523(10) . ? C16 C18 1.516(11) . ? C16 C17 1.543(12) . ? C19 Cl2 1.670(8) . ? C19 Cl3 1.687(8) . ? C19 Cl1 1.705(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 O1 C4 C1 110.0(5) . . ? O1 C4 C3 101.8(5) . . ? C1 C4 C3 113.3(6) . . ? O1 C4 C2 108.2(5) . . ? C1 C4 C2 113.9(6) . . ? C3 C4 C2 108.9(6) . . ? O2 C5 N1 124.8(6) . . ? O2 C5 O1 123.3(6) . . ? N1 C5 O1 111.9(5) . . ? N1 C6 C7 110.9(5) . . ? N1 C6 C9 111.3(4) . . ? C7 C6 C9 110.3(5) . . ? N1 C6 C8 108.2(5) . . ? C7 C6 C8 109.5(5) . . ? C9 C6 C8 106.5(5) . . ? O3 C9 N2 121.2(5) . . ? O3 C9 C6 122.0(5) . . ? N2 C9 C6 116.7(5) . . ? N2 C10 C12 113.9(4) . . ? N2 C10 C11 108.3(4) . . ? C12 C10 C11 110.8(4) . . ? O4 C12 N3 123.6(6) . . ? O4 C12 C10 120.3(5) . . ? N3 C12 C10 116.0(5) . . ? N3 C13 C15 112.9(5) . . ? N3 C13 C14 108.5(4) . . ? C15 C13 C14 110.7(5) . . ? O5 C14 C13 113.1(5) . . ? C13 C15 C16 119.3(7) . . ? C18 C16 C15 112.3(9) . . ? C18 C16 C17 111.0(8) . . ? C15 C16 C17 111.0(7) . . ? Cl2 C19 Cl3 113.3(5) . . ? Cl2 C19 Cl1 109.6(5) . . ? Cl3 C19 Cl1 107.2(5) . . ? C5 N1 C6 121.3(5) . . ? C9 N2 C10 120.9(5) . . ? C12 N3 C13 123.9(5) . . ? C5 O1 C4 121.9(5) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.444 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.049 data_mo_svj_boc_av_alcohol_0m _database_code_depnum_ccdc_archive 'CCDC 805264' #TrackingRef 'Ala-Val-ol.gus' _audit_creation_method SHELXL-97 _chemical_name_systematic 'Dipeptide alcohol' _chemical_name_common 'Dipeptide alcohol' _chemical_formula_moiety 'C13 H26 N2 O4' _chemical_formula_sum 'C13 H26 N2 O4' _chemical_compound_source Synthesis _exptl_crystal_recrystallization_method Chloroform _chemical_melting_point ? _exptl_crystal_description cubic _exptl_crystal_colour colourless _diffrn_ambient_temperature 200 _diffrn_ambient_pressure 101.325 _chemical_formula_weight 274.36 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 9.704(3) _cell_length_b 13.077(3) _cell_length_c 25.661(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3256.3(15) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.119 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 37822 _diffrn_reflns_av_R_equivalents 0.1342 _diffrn_reflns_av_sigmaI/netI 0.0756 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 22.02 _reflns_number_total 3995 _reflns_number_gt 2585 _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^)+(0.0000P)^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 0.0016(3) _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 1(2) _refine_ls_number_reflns 3995 _refine_ls_number_parameters 358 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1186 _refine_ls_R_factor_gt 0.0653 _refine_ls_wR_factor_ref 0.1069 _refine_ls_wR_factor_gt 0.0964 _refine_ls_goodness_of_fit_ref 1.592 _refine_ls_restrained_S_all 1.592 _refine_ls_shift/su_max 2.947 _refine_ls_shift/su_mean 0.082 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 0.4670(6) 0.9866(4) 0.0548(2) 0.079(2) Uani 1 1 d . . . H1A H 0.4409 0.9160 0.0519 0.118 Uiso 1 1 calc R . . H1B H 0.4848 1.0140 0.0208 0.118 Uiso 1 1 calc R . . H1C H 0.3936 1.0244 0.0709 0.118 Uiso 1 1 calc R . . C2 C 0.7155(6) 0.9428(4) 0.0602(2) 0.085(2) Uani 1 1 d . . . H2A H 0.7954 0.9452 0.0822 0.127 Uiso 1 1 calc R . . H2B H 0.7346 0.9774 0.0280 0.127 Uiso 1 1 calc R . . H2C H 0.6921 0.8728 0.0532 0.127 Uiso 1 1 calc R . . C3 C 0.5949(6) 0.9952(4) 0.0876(2) 0.0534(17) Uani 1 1 d . . . C4 C 0.6291(6) 1.1032(4) 0.1010(2) 0.071(2) Uani 1 1 d . . . H4A H 0.5533 1.1335 0.1194 0.106 Uiso 1 1 calc R . . H4B H 0.6459 1.1410 0.0695 0.106 Uiso 1 1 calc R . . H4C H 0.7100 1.1048 0.1225 0.106 Uiso 1 1 calc R . . C5 C 0.4792(6) 0.9509(5) 0.1701(2) 0.0472(15) Uani 1 1 d . . . C6 C 0.3783(5) 0.8803(4) 0.2472(2) 0.0432(15) Uani 1 1 d . . . H6 H 0.2911 0.9084 0.2344 0.052 Uiso 1 1 calc R . . C7 C 0.3520(6) 0.7705(4) 0.2674(2) 0.0599(18) Uani 1 1 d . . . H7A H 0.3174 0.7289 0.2395 0.090 Uiso 1 1 calc R . . H7B H 0.2856 0.7726 0.2952 0.090 Uiso 1 1 calc R . . H7C H 0.4367 0.7420 0.2802 0.090 Uiso 1 1 calc R . . C8 C 0.4287(6) 0.9465(4) 0.2922(2) 0.0437(15) Uani 1 1 d . . . C9 C 0.3453(5) 1.0517(4) 0.3661(2) 0.0446(15) Uani 1 1 d . . . H9 H 0.2522 1.0701 0.3775 0.053 Uiso 1 1 calc R . . C10 C 0.4121(6) 0.9965(4) 0.4116(2) 0.0589(17) Uani 1 1 d . . . H10 H 0.5089 0.9839 0.4028 0.071 Uiso 1 1 calc R . . C11 C 0.3439(8) 0.8953(4) 0.4222(2) 0.106(3) Uani 1 1 d . . . H11A H 0.2464 0.9052 0.4261 0.159 Uiso 1 1 calc R . . H11B H 0.3808 0.8666 0.4537 0.159 Uiso 1 1 calc R . . H11C H 0.3610 0.8496 0.3937 0.159 Uiso 1 1 calc R . . C12 C 0.4069(7) 1.0616(5) 0.4614(2) 0.085(2) Uani 1 1 d . . . H12A H 0.3127 1.0717 0.4716 0.128 Uiso 1 1 calc R . . H12B H 0.4493 1.1267 0.4549 0.128 Uiso 1 1 calc R . . H12C H 0.4556 1.0271 0.4888 0.128 Uiso 1 1 calc R . . C13 C 0.4160(6) 1.1502(4) 0.3518(2) 0.0541(17) Uani 1 1 d . . . H13A H 0.4091 1.1971 0.3810 0.065 Uiso 1 1 calc R . . H13B H 0.5130 1.1365 0.3460 0.065 Uiso 1 1 calc R . . C14 C -0.0097(5) 0.7131(4) 0.0650(2) 0.0677(18) Uani 1 1 d . . . H14A H -0.0141 0.6404 0.0603 0.102 Uiso 1 1 calc R . . H14B H -0.0003 0.7458 0.0317 0.102 Uiso 1 1 calc R . . H14C H -0.0927 0.7364 0.0816 0.102 Uiso 1 1 calc R . . C15 C 0.1168(6) 0.8531(4) 0.1121(2) 0.070(2) Uani 1 1 d . . . H15A H 0.0306 0.8733 0.1274 0.106 Uiso 1 1 calc R . . H15B H 0.1329 0.8922 0.0811 0.106 Uiso 1 1 calc R . . H15C H 0.1900 0.8653 0.1366 0.106 Uiso 1 1 calc R . . C16 C 0.1120(6) 0.7393(5) 0.0985(2) 0.0512(16) Uani 1 1 d . . . C17 C 0.2460(5) 0.7039(5) 0.0731(2) 0.084(2) Uani 1 1 d . . . H17A H 0.3227 0.7246 0.0943 0.126 Uiso 1 1 calc R . . H17B H 0.2542 0.7340 0.0392 0.126 Uiso 1 1 calc R . . H17C H 0.2455 0.6307 0.0700 0.126 Uiso 1 1 calc R . . C18 C 0.0056(7) 0.6874(5) 0.1804(2) 0.0503(16) Uani 1 1 d . . . C19 C 0.1211(6) 0.5418(4) 0.2246(2) 0.0534(16) Uani 1 1 d . . . H19 H 0.2101 0.5643 0.2107 0.064 Uiso 1 1 calc R . . C20 C 0.1387(6) 0.5113(5) 0.2818(2) 0.086(2) Uani 1 1 d . . . H20A H 0.0514 0.4901 0.2957 0.128 Uiso 1 1 calc R . . H20B H 0.1723 0.5688 0.3013 0.128 Uiso 1 1 calc R . . H20C H 0.2033 0.4560 0.2843 0.128 Uiso 1 1 calc R . . C21 C 0.0709(6) 0.4509(4) 0.1937(2) 0.0500(16) Uani 1 1 d . . . C22 C 0.1345(6) 0.2900(4) 0.1529(3) 0.0624(18) Uani 1 1 d . . . H22 H 0.0419 0.2754 0.1662 0.075 Uiso 1 1 calc R . . C23 C 0.1118(16) 0.3063(10) 0.0924(5) 0.238(8) Uani 1 1 d . . . H23 H 0.0516 0.3653 0.0863 0.286 Uiso 1 1 calc R . . C24 C 0.2459(10) 0.3237(8) 0.0692(4) 0.205(6) Uani 1 1 d . . . H25A H 0.2873 0.3831 0.0847 0.308 Uiso 1 1 calc R . . H25B H 0.2356 0.3344 0.0324 0.308 Uiso 1 1 calc R . . H25C H 0.3036 0.2653 0.0752 0.308 Uiso 1 1 calc R . . C25 C 0.2257(7) 0.2157(5) 0.1821(5) 0.164(5) Uani 1 1 d . . . H26A H 0.3055 0.2026 0.1604 0.196 Uiso 1 1 calc R . . H26B H 0.2586 0.2505 0.2130 0.196 Uiso 1 1 calc R . . C26 C 0.0639(19) 0.2282(13) 0.0704(5) 0.425(15) Uani 1 1 d . . . H50A H 0.1331 0.1986 0.0483 0.637 Uiso 1 1 calc R . . H50B H -0.0147 0.2470 0.0498 0.637 Uiso 1 1 calc R . . H50C H 0.0366 0.1792 0.0963 0.637 Uiso 1 1 calc R . . N1 N 0.4742(4) 0.8766(3) 0.20489(17) 0.0437(12) Uani 1 1 d . . . H1 H 0.5291 0.8253 0.2021 0.052 Uiso 1 1 calc R . . N2 N 0.3288(4) 0.9876(3) 0.32008(15) 0.0367(11) Uani 1 1 d . . . H2 H 0.2458 0.9754 0.3101 0.044 Uiso 1 1 calc R . . N3 N 0.0234(5) 0.6260(4) 0.22195(18) 0.0531(13) Uani 1 1 d . . . H3 H -0.0268 0.6375 0.2490 0.064 Uiso 1 1 calc R . . N4 N 0.1668(4) 0.3886(4) 0.17475(17) 0.0538(13) Uani 1 1 d . . . H4 H 0.2515 0.4079 0.1755 0.065 Uiso 1 1 calc R . . O1 O 0.5815(4) 0.9315(3) 0.13468(14) 0.0509(11) Uani 1 1 d . . . O2 O 0.4080(4) 1.0267(3) 0.16894(15) 0.0705(14) Uani 1 1 d . . . O3 O 0.5523(4) 0.9555(3) 0.30254(14) 0.0565(11) Uani 1 1 d . . . O4 O 0.3613(3) 1.1989(3) 0.30668(15) 0.0539(11) Uani 1 1 d . . . H4D H 0.2774 1.2037 0.3095 0.081 Uiso 1 1 calc R . . O5 O 0.1098(4) 0.6776(3) 0.14661(14) 0.0528(11) Uani 1 1 d . . . O6 O -0.0902(4) 0.7472(3) 0.17561(15) 0.0604(12) Uani 1 1 d . . . O7 O -0.0533(4) 0.4343(3) 0.18817(16) 0.0727(14) Uani 1 1 d . . . O8 O 0.1815(5) 0.1341(4) 0.1957(2) 0.116(2) Uani 1 1 d . . . H8 H 0.2423 0.0909 0.1933 0.174 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 0.075(5) 0.085(5) 0.076(5) 0.012(4) -0.022(4) -0.017(4) C2 0.097(6) 0.083(5) 0.075(5) 0.019(4) 0.039(4) 0.028(4) C3 0.069(5) 0.046(4) 0.045(4) 0.006(3) 0.003(4) 0.003(4) C4 0.084(5) 0.054(5) 0.074(5) -0.007(4) 0.009(4) -0.004(4) C5 0.047(4) 0.043(4) 0.052(4) -0.003(4) 0.004(4) -0.004(3) C6 0.037(4) 0.047(4) 0.045(4) -0.005(3) 0.002(3) 0.001(3) C7 0.071(4) 0.041(4) 0.068(5) -0.008(3) 0.015(4) -0.016(3) C8 0.038(4) 0.045(4) 0.048(4) -0.008(3) 0.009(3) -0.004(3) C9 0.035(3) 0.048(4) 0.051(4) -0.003(3) -0.002(3) -0.003(3) C10 0.064(4) 0.064(5) 0.048(4) -0.002(4) -0.005(3) 0.014(4) C11 0.191(9) 0.058(5) 0.068(5) 0.029(4) -0.033(5) -0.029(6) C12 0.120(6) 0.097(5) 0.039(4) -0.007(4) -0.010(4) 0.008(5) C13 0.056(4) 0.060(4) 0.046(4) -0.010(3) -0.001(3) -0.006(3) C14 0.057(4) 0.086(5) 0.060(5) -0.002(4) -0.018(4) 0.010(4) C15 0.072(5) 0.072(5) 0.068(5) -0.004(4) -0.008(4) -0.017(4) C16 0.045(4) 0.062(5) 0.047(4) 0.004(4) -0.004(3) 0.001(4) C17 0.054(4) 0.128(6) 0.069(5) 0.013(4) 0.018(4) 0.028(5) C18 0.045(4) 0.046(4) 0.060(5) -0.004(4) 0.003(4) -0.010(4) C19 0.037(4) 0.058(4) 0.065(5) 0.006(4) -0.002(3) -0.009(4) C20 0.093(5) 0.103(6) 0.061(5) 0.016(4) -0.037(4) -0.004(4) C21 0.048(4) 0.053(4) 0.049(4) -0.007(3) 0.004(4) -0.002(4) C22 0.049(4) 0.036(4) 0.103(6) 0.010(4) 0.009(4) 0.007(4) C23 0.335(18) 0.229(14) 0.151(12) -0.146(10) 0.156(12) -0.190(13) C24 0.227(13) 0.247(12) 0.141(9) -0.072(9) 0.080(9) -0.135(11) C25 0.047(5) 0.051(6) 0.393(16) 0.083(8) 0.014(7) 0.004(4) C26 0.66(4) 0.45(3) 0.162(14) -0.124(16) 0.177(18) -0.29(3) N1 0.051(3) 0.035(3) 0.045(3) 0.001(3) 0.008(3) 0.015(3) N2 0.027(2) 0.043(3) 0.041(3) -0.004(2) 0.000(2) -0.004(2) N3 0.049(3) 0.063(4) 0.047(3) -0.004(3) 0.018(3) 0.004(3) N4 0.029(3) 0.060(4) 0.072(4) 0.006(3) 0.000(3) 0.005(3) O1 0.054(3) 0.048(3) 0.051(3) 0.004(2) 0.017(2) 0.012(2) O2 0.077(3) 0.051(3) 0.083(3) 0.011(2) 0.024(3) 0.034(2) O3 0.027(2) 0.068(3) 0.075(3) -0.018(2) 0.003(2) 0.001(2) O4 0.048(2) 0.048(2) 0.066(3) 0.001(2) -0.002(2) -0.009(2) O5 0.036(2) 0.075(3) 0.048(3) 0.010(2) 0.005(2) 0.014(2) O6 0.052(3) 0.051(3) 0.078(3) 0.002(2) 0.005(2) 0.014(2) O7 0.019(2) 0.069(3) 0.129(4) -0.009(3) -0.006(2) 0.003(2) O8 0.104(4) 0.131(5) 0.113(4) 0.064(4) 0.064(4) 0.065(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 C3 1.504(7) . ? C2 C3 1.528(7) . ? C3 O1 1.472(6) . ? C3 C4 1.491(7) . ? C5 O2 1.208(6) . ? C5 N1 1.320(6) . ? C5 O1 1.370(6) . ? C6 N1 1.431(6) . ? C6 C7 1.547(6) . ? C6 C8 1.523(7) . ? C8 O3 1.234(5) . ? C8 N2 1.320(6) . ? C9 N2 1.457(6) . ? C9 C13 1.506(6) . ? C9 C10 1.516(7) . ? C10 C11 1.505(7) . ? C10 C12 1.537(7) . ? C13 O4 1.423(5) . ? C14 C16 1.501(7) . ? C15 C16 1.530(7) . ? C16 O5 1.474(6) . ? C16 C17 1.527(7) . ? C18 O6 1.221(6) . ? C18 N3 1.346(6) . ? C18 O5 1.337(6) . ? C19 N3 1.455(6) . ? C19 C20 1.531(6) . ? C19 C21 1.509(7) . ? C21 O7 1.233(6) . ? C21 N4 1.330(6) . ? C22 N4 1.440(6) . ? C22 C25 1.512(8) . ? C22 C23 1.583(13) . ? C23 C26 1.258(13) . ? C23 C24 1.448(13) . ? C25 O8 1.201(7) . ? 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 C3 C4 111.6(5) . . ? O1 C3 C2 101.0(4) . . ? C4 C3 C2 111.1(5) . . ? O1 C3 C1 110.1(5) . . ? C4 C3 C1 112.5(5) . . ? C2 C3 C1 109.9(5) . . ? O2 C5 N1 126.9(6) . . ? O2 C5 O1 123.3(6) . . ? N1 C5 O1 109.8(5) . . ? N1 C6 C7 109.3(4) . . ? N1 C6 C8 112.7(4) . . ? C7 C6 C8 109.0(4) . . ? O3 C8 N2 124.0(5) . . ? O3 C8 C6 122.0(5) . . ? N2 C8 C6 114.0(5) . . ? N2 C9 C13 110.1(4) . . ? N2 C9 C10 113.4(4) . . ? C13 C9 C10 113.6(5) . . ? C11 C10 C9 111.7(5) . . ? C11 C10 C12 108.8(5) . . ? C9 C10 C12 111.3(5) . . ? O4 C13 C9 114.3(4) . . ? O5 C16 C14 110.1(5) . . ? O5 C16 C17 101.7(4) . . ? C14 C16 C17 110.9(5) . . ? O5 C16 C15 110.0(4) . . ? C14 C16 C15 112.2(5) . . ? C17 C16 C15 111.5(5) . . ? O6 C18 N3 123.9(6) . . ? O6 C18 O5 124.9(6) . . ? N3 C18 O5 111.1(6) . . ? N3 C19 C20 108.3(5) . . ? N3 C19 C21 111.2(5) . . ? C20 C19 C21 109.6(5) . . ? O7 C21 N4 122.3(6) . . ? O7 C21 C19 121.0(6) . . ? N4 C21 C19 116.7(5) . . ? N4 C22 C25 104.8(6) . . ? N4 C22 C23 106.9(6) . . ? C25 C22 C23 130.8(8) . . ? C26 C23 C24 106.0(12) . . ? C26 C23 C22 112.5(14) . . ? C24 C23 C22 107.4(12) . . ? O8 C25 C22 120.4(7) . . ? C5 N1 C6 120.8(5) . . ? C8 N2 C9 126.3(4) . . ? C18 N3 C19 124.9(5) . . ? C21 N4 C22 122.6(5) . . ? C5 O1 C3 120.2(4) . . ? C18 O5 C16 120.0(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 22.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.320 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.054