# Electronic Supplementary Material (ESI) for Organic and Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'G Sanjayan' _publ_contact_author_email GJ.SANJAYAN@NCL.RES.IN _publ_section_title ; Concurrent Display of Both alpha- and beta-Turns in a Semi Synthetic Peptide ; loop_ _publ_author_name 'G Sanjayan' 'Rajesh Gonnade' 'Usha D Phalgune' 'Pattuparambil R Rajamohanan' 'Deekonda Srinivas' # Attachment '2.cif' data_shrini _database_code_depnum_ccdc_archive 'CCDC 663336' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H37 N5 O7 . H2O' _chemical_formula_sum 'C21 H39 N5 O8' _chemical_formula_weight 489.57 _chemical_absolute_configuration syn 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 P2(1)2(1)2(1) 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 9.0917(8) _cell_length_b 9.8531(9) _cell_length_c 29.228(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2618.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 1225 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 21.37 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.242 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9501 _exptl_absorpt_correction_T_max 0.9938 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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_device 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13265 _diffrn_reflns_av_R_equivalents 0.0376 _diffrn_reflns_av_sigmaI/netI 0.0442 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 24.99 _reflns_number_total 4607 _reflns_number_gt 3636 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SAINT' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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^)+(0.0627P)^2^+0.2392P] 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 0.4(17) _refine_ls_number_reflns 4607 _refine_ls_number_parameters 321 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0855 _refine_ls_R_factor_gt 0.0641 _refine_ls_wR_factor_ref 0.1411 _refine_ls_wR_factor_gt 0.1324 _refine_ls_goodness_of_fit_ref 1.116 _refine_ls_restrained_S_all 1.116 _refine_ls_shift/su_max 0.069 _refine_ls_shift/su_mean 0.003 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 0.5663(2) 0.3748(2) 0.01549(7) 0.0513(6) Uani 1 1 d . . . O3 O 0.3046(2) 0.5397(2) -0.04994(8) 0.0540(6) Uani 1 1 d . . . N2 N 0.5256(3) 0.1390(3) 0.06496(8) 0.0500(7) Uani 1 1 d . . . H2 H 0.6071 0.0955 0.0676 0.060 Uiso 1 1 calc R . . C1 C 0.5033(3) 0.2804(3) -0.00395(10) 0.0414(7) Uani 1 1 d . . . N1 N 0.4667(3) 0.2880(2) -0.04831(8) 0.0415(6) Uani 1 1 d . . . N4 N 0.4946(3) 0.6676(3) 0.04583(9) 0.0542(7) Uani 1 1 d . . . H4 H 0.5619 0.6180 0.0337 0.065 Uiso 1 1 calc R . . C2 C 0.4392(3) 0.5343(3) -0.05640(9) 0.0401(7) Uani 1 1 d . . . N3 N 0.5267(3) 0.6382(2) -0.04846(8) 0.0452(6) Uani 1 1 d . . . H3 H 0.6190 0.6315 -0.0544 0.054 Uiso 1 1 calc R . . O4 O 0.3355(3) 0.8381(3) 0.03517(10) 0.0795(8) Uani 1 1 d . . . O7 O 0.3449(3) 0.2473(3) 0.10288(8) 0.0760(8) Uani 1 1 d . . . C3 C 1.0002(4) 0.7285(4) 0.18788(12) 0.0652(10) Uani 1 1 d . . . O8 O 0.5516(3) 0.1727(3) 0.13879(7) 0.0707(7) Uani 1 1 d . . . C4 C 0.4525(5) 0.3734(4) -0.12342(11) 0.0655(10) Uani 1 1 d . . . H4A H 0.3567 0.4140 -0.1285 0.079 Uiso 1 1 calc R . . H4B H 0.5200 0.4062 -0.1466 0.079 Uiso 1 1 calc R . . O6 O 0.8879(3) 0.7707(3) 0.15516(9) 0.0759(8) Uani 1 1 d . . . O2 O 0.2122(3) 0.4555(3) 0.04654(13) 0.0888(9) Uani 1 1 d . . . C5 C 0.4690(4) 0.7641(3) -0.02975(12) 0.0573(9) Uani 1 1 d . . . H5A H 0.3834 0.7905 -0.0475 0.069 Uiso 1 1 calc R . . H5B H 0.5426 0.8344 -0.0335 0.069 Uiso 1 1 calc R . . C6 C 0.5095(4) 0.4063(3) -0.07519(9) 0.0450(8) Uani 1 1 d . . . H6 H 0.6168 0.4155 -0.0755 0.054 Uiso 1 1 calc R . . C7 C 0.4260(3) 0.7579(3) 0.01992(13) 0.0514(8) Uani 1 1 d . . . C8 C 0.4645(4) 0.1924(3) 0.10221(11) 0.0515(8) Uani 1 1 d . . . C9 C 0.5082(4) 0.7665(5) 0.12354(13) 0.0743(12) Uani 1 1 d . . . H9A H 0.4641 0.8491 0.1118 0.089 Uiso 1 1 calc R . . H9B H 0.4711 0.7523 0.1543 0.089 Uiso 1 1 calc R . . N5 N 0.6665(3) 0.7846(4) 0.12573(10) 0.0695(9) Uani 1 1 d . . . H5 H 0.7095 0.8299 0.1044 0.083 Uiso 1 1 calc R . . C10 C 0.7474(4) 0.7336(5) 0.15945(13) 0.0696(11) Uani 1 1 d . . . C11 C 0.4430(5) 0.2241(4) -0.12435(12) 0.0744(11) Uani 1 1 d . . . H11A H 0.5370 0.1851 -0.1329 0.089 Uiso 1 1 calc R . . H11B H 0.3695 0.1949 -0.1463 0.089 Uiso 1 1 calc R . . C12 C 0.4606(5) 0.6490(4) 0.09386(12) 0.0723(11) Uani 1 1 d . . . H12A H 0.5084 0.5670 0.1046 0.087 Uiso 1 1 calc R . . H12B H 0.3553 0.6364 0.0972 0.087 Uiso 1 1 calc R . . O5 O 0.6993(4) 0.6668(5) 0.18941(10) 0.1422(18) Uani 1 1 d . . . C13 C 0.4604(4) 0.1517(3) 0.02056(10) 0.0510(8) Uani 1 1 d . . . H13A H 0.3542 0.1492 0.0237 0.061 Uiso 1 1 calc R . . H13B H 0.4895 0.0745 0.0021 0.061 Uiso 1 1 calc R . . C14 C 0.4968(4) 0.1958(4) 0.18543(11) 0.0703(11) Uani 1 1 d . . . C15 C 0.4005(4) 0.1800(3) -0.07671(11) 0.0546(9) Uani 1 1 d . . . H15A H 0.2945 0.1770 -0.0731 0.065 Uiso 1 1 calc R . . H15B H 0.4414 0.0918 -0.0693 0.065 Uiso 1 1 calc R . . C16 C 0.9636(6) 0.7828(11) 0.2331(2) 0.202(5) Uani 1 1 d . . . H16A H 0.9055 0.8635 0.2297 0.302 Uiso 1 1 calc R . . H16B H 1.0525 0.8041 0.2493 0.302 Uiso 1 1 calc R . . H16C H 0.9087 0.7163 0.2500 0.302 Uiso 1 1 calc R . . C17 C 0.6263(6) 0.1490(7) 0.21432(14) 0.122(2) Uani 1 1 d . . . H17A H 0.6517 0.0576 0.2062 0.184 Uiso 1 1 calc R . . H17B H 0.6000 0.1526 0.2461 0.184 Uiso 1 1 calc R . . H17C H 0.7090 0.2074 0.2089 0.184 Uiso 1 1 calc R . . C18 C 0.3687(5) 0.1063(5) 0.19404(13) 0.0963(15) Uani 1 1 d . . . H18A H 0.2872 0.1354 0.1756 0.144 Uiso 1 1 calc R . . H18B H 0.3421 0.1111 0.2258 0.144 Uiso 1 1 calc R . . H18C H 0.3938 0.0145 0.1863 0.144 Uiso 1 1 calc R . . C19 C 1.1355(5) 0.7942(8) 0.1710(2) 0.149(3) Uani 1 1 d . . . H19A H 1.1535 0.7667 0.1400 0.223 Uiso 1 1 calc R . . H19B H 1.2171 0.7676 0.1899 0.223 Uiso 1 1 calc R . . H19C H 1.1241 0.8910 0.1723 0.223 Uiso 1 1 calc R . . C20 C 0.4611(8) 0.3430(5) 0.19261(16) 0.128(2) Uani 1 1 d . . . H20A H 0.5443 0.3974 0.1841 0.192 Uiso 1 1 calc R . . H20B H 0.4383 0.3583 0.2243 0.192 Uiso 1 1 calc R . . H20C H 0.3780 0.3674 0.1741 0.192 Uiso 1 1 calc R . . C21 C 1.0124(11) 0.5822(6) 0.1875(3) 0.248(6) Uani 1 1 d . . . H21A H 0.9310 0.5442 0.1710 0.372 Uiso 1 1 calc R . . H21B H 1.0115 0.5489 0.2184 0.372 Uiso 1 1 calc R . . H21C H 1.1028 0.5563 0.1730 0.372 Uiso 1 1 calc R . . H42 H 0.288(8) 0.399(8) 0.067(2) 0.21(3) Uiso 1 1 d . . . H41 H 0.284(10) 0.478(9) 0.013(3) 0.23(3) Uiso 1 1 d . . . 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 0.0640(14) 0.0405(12) 0.0494(12) -0.0040(10) -0.0123(11) -0.0020(11) O3 0.0370(13) 0.0486(13) 0.0765(15) 0.0049(12) -0.0038(11) -0.0011(10) N2 0.0561(16) 0.0536(16) 0.0403(14) 0.0030(12) 0.0033(12) 0.0129(14) C1 0.0417(17) 0.0386(16) 0.0438(18) -0.0019(13) 0.0024(13) 0.0054(14) N1 0.0510(14) 0.0358(13) 0.0378(14) 0.0010(11) -0.0041(12) 0.0021(12) N4 0.0526(16) 0.0513(17) 0.0588(17) -0.0068(14) 0.0085(14) 0.0045(14) C2 0.0388(18) 0.0429(17) 0.0385(17) 0.0110(13) -0.0051(13) -0.0047(14) N3 0.0383(13) 0.0413(14) 0.0558(15) 0.0035(12) -0.0028(12) -0.0031(12) O4 0.0475(14) 0.0637(16) 0.127(2) -0.0193(16) 0.0127(15) 0.0081(13) O7 0.0612(16) 0.105(2) 0.0621(15) -0.0048(15) 0.0019(12) 0.0267(16) C3 0.067(2) 0.070(2) 0.059(2) 0.0062(18) -0.0045(18) -0.003(2) O8 0.0574(14) 0.115(2) 0.0399(13) 0.0055(13) -0.0008(11) 0.0080(15) C4 0.082(3) 0.070(3) 0.045(2) -0.0009(17) 0.0039(18) -0.003(2) O6 0.0561(16) 0.097(2) 0.0746(17) 0.0232(16) 0.0027(13) -0.0116(14) O2 0.0630(17) 0.088(2) 0.115(2) 0.0068(19) 0.0041(18) -0.0053(16) C5 0.0537(19) 0.0418(18) 0.076(2) 0.0092(16) -0.0104(17) -0.0039(16) C6 0.0438(18) 0.0500(19) 0.0413(17) 0.0029(14) 0.0011(13) -0.0037(15) C7 0.0346(17) 0.0379(17) 0.082(2) -0.0064(18) -0.0022(16) -0.0051(15) C8 0.051(2) 0.056(2) 0.0472(19) 0.0021(16) 0.0029(16) 0.0010(17) C9 0.052(2) 0.105(3) 0.066(2) -0.022(2) 0.0171(17) -0.020(2) N5 0.0557(19) 0.092(2) 0.0610(19) 0.0074(17) 0.0091(15) -0.0157(17) C10 0.072(3) 0.097(3) 0.040(2) 0.002(2) 0.0032(18) -0.031(2) C11 0.103(3) 0.069(3) 0.052(2) -0.0115(18) -0.018(2) 0.000(2) C12 0.070(2) 0.077(3) 0.070(2) -0.008(2) 0.015(2) -0.021(2) O5 0.108(3) 0.247(5) 0.072(2) 0.067(3) -0.0179(18) -0.095(3) C13 0.063(2) 0.0451(18) 0.0453(18) -0.0028(14) -0.0001(16) 0.0006(16) C14 0.079(3) 0.092(3) 0.0401(19) -0.0089(18) 0.0063(18) -0.008(2) C15 0.063(2) 0.045(2) 0.056(2) -0.0087(16) -0.0089(16) 0.0009(17) C16 0.082(4) 0.403(13) 0.120(5) -0.126(7) -0.008(3) -0.028(6) C17 0.099(4) 0.222(7) 0.046(2) 0.018(3) -0.011(2) -0.007(4) C18 0.105(4) 0.126(4) 0.058(3) -0.003(3) 0.023(2) -0.021(3) C19 0.054(3) 0.225(8) 0.167(6) 0.097(5) -0.006(3) 0.010(4) C20 0.207(7) 0.101(4) 0.076(3) -0.024(3) 0.005(4) -0.015(4) C21 0.278(11) 0.064(4) 0.402(14) 0.014(6) -0.211(11) 0.011(5) _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 1.231(3) . ? O3 C2 1.239(4) . ? N2 C8 1.331(4) . ? N2 C13 1.432(4) . ? C1 N1 1.340(4) . ? C1 C13 1.508(4) . ? N1 C6 1.458(4) . ? N1 C15 1.478(4) . ? N4 C7 1.324(4) . ? N4 C12 1.449(4) . ? C2 N3 1.317(4) . ? C2 C6 1.517(4) . ? N3 C5 1.454(4) . ? O4 C7 1.225(4) . ? O7 C8 1.214(4) . ? C3 C21 1.446(7) . ? C3 O6 1.459(4) . ? C3 C16 1.464(7) . ? C3 C19 1.475(6) . ? O8 C8 1.345(4) . ? O8 C14 1.469(4) . ? C4 C11 1.474(5) . ? C4 C6 1.537(4) . ? O6 C10 1.335(4) . ? C5 C7 1.505(5) . ? C9 N5 1.452(5) . ? C9 C12 1.510(5) . ? N5 C10 1.328(5) . ? C10 O5 1.179(4) . ? C11 C15 1.509(5) . ? C14 C18 1.483(6) . ? C14 C20 1.501(7) . ? C14 C17 1.520(6) . ? 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 C8 N2 C13 122.3(3) . . ? O1 C1 N1 121.3(3) . . ? O1 C1 C13 122.4(3) . . ? N1 C1 C13 116.2(3) . . ? C1 N1 C6 120.0(2) . . ? C1 N1 C15 127.2(2) . . ? C6 N1 C15 112.4(2) . . ? C7 N4 C12 122.6(3) . . ? O3 C2 N3 122.4(3) . . ? O3 C2 C6 120.5(3) . . ? N3 C2 C6 117.1(3) . . ? C2 N3 C5 120.8(3) . . ? C21 C3 O6 109.4(4) . . ? C21 C3 C16 112.8(7) . . ? O6 C3 C16 109.2(4) . . ? C21 C3 C19 111.8(6) . . ? O6 C3 C19 103.9(3) . . ? C16 C3 C19 109.3(5) . . ? C8 O8 C14 121.1(3) . . ? C11 C4 C6 104.3(3) . . ? C10 O6 C3 122.0(3) . . ? N3 C5 C7 115.0(3) . . ? N1 C6 C2 110.9(2) . . ? N1 C6 C4 103.6(2) . . ? C2 C6 C4 111.4(3) . . ? O4 C7 N4 122.8(4) . . ? O4 C7 C5 120.0(3) . . ? N4 C7 C5 117.2(3) . . ? O7 C8 N2 124.3(3) . . ? O7 C8 O8 125.4(3) . . ? N2 C8 O8 110.3(3) . . ? N5 C9 C12 113.8(3) . . ? C10 N5 C9 122.3(3) . . ? O5 C10 N5 123.8(4) . . ? O5 C10 O6 125.3(4) . . ? N5 C10 O6 110.9(3) . . ? C4 C11 C15 106.6(3) . . ? N4 C12 C9 113.5(3) . . ? N2 C13 C1 113.4(3) . . ? O8 C14 C18 109.4(3) . . ? O8 C14 C20 110.7(3) . . ? C18 C14 C20 112.4(4) . . ? O8 C14 C17 101.9(3) . . ? C18 C14 C17 109.5(4) . . ? C20 C14 C17 112.5(4) . . ? N1 C15 C11 101.9(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 O1 C1 N1 C6 3.8(4) . . . . ? C13 C1 N1 C6 -177.3(3) . . . . ? O1 C1 N1 C15 175.5(3) . . . . ? C13 C1 N1 C15 -5.6(4) . . . . ? O3 C2 N3 C5 2.5(4) . . . . ? C6 C2 N3 C5 -179.0(2) . . . . ? C21 C3 O6 C10 62.0(7) . . . . ? C16 C3 O6 C10 -62.0(6) . . . . ? C19 C3 O6 C10 -178.5(5) . . . . ? C2 N3 C5 C7 72.5(4) . . . . ? C1 N1 C6 C2 -62.2(3) . . . . ? C15 N1 C6 C2 124.9(3) . . . . ? C1 N1 C6 C4 178.1(3) . . . . ? C15 N1 C6 C4 5.3(3) . . . . ? O3 C2 C6 N1 -52.3(4) . . . . ? N3 C2 C6 N1 129.1(3) . . . . ? O3 C2 C6 C4 62.6(4) . . . . ? N3 C2 C6 C4 -116.0(3) . . . . ? C11 C4 C6 N1 -23.8(4) . . . . ? C11 C4 C6 C2 -143.1(3) . . . . ? C12 N4 C7 O4 4.7(5) . . . . ? C12 N4 C7 C5 -178.3(3) . . . . ? N3 C5 C7 O4 -156.3(3) . . . . ? N3 C5 C7 N4 26.6(4) . . . . ? C13 N2 C8 O7 5.5(5) . . . . ? C13 N2 C8 O8 -176.5(3) . . . . ? C14 O8 C8 O7 10.9(5) . . . . ? C14 O8 C8 N2 -167.0(3) . . . . ? C12 C9 N5 C10 -95.9(4) . . . . ? C9 N5 C10 O5 2.3(7) . . . . ? C9 N5 C10 O6 -176.4(3) . . . . ? C3 O6 C10 O5 1.2(7) . . . . ? C3 O6 C10 N5 179.8(3) . . . . ? C6 C4 C11 C15 34.0(4) . . . . ? C7 N4 C12 C9 -69.9(4) . . . . ? N5 C9 C12 N4 -65.7(5) . . . . ? C8 N2 C13 C1 86.5(4) . . . . ? O1 C1 C13 N2 -12.0(4) . . . . ? N1 C1 C13 N2 169.1(2) . . . . ? C8 O8 C14 C18 59.2(5) . . . . ? C8 O8 C14 C20 -65.1(5) . . . . ? C8 O8 C14 C17 175.1(4) . . . . ? C1 N1 C15 C11 -157.4(3) . . . . ? C6 N1 C15 C11 14.8(4) . . . . ? C4 C11 C15 N1 -30.0(4) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.221 _refine_diff_density_min -0.142 _refine_diff_density_rms 0.039 # Attachment '1a.CIF' data_dsbzp _database_code_depnum_ccdc_archive 'CCDC 680778' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H24 N4 O4' _chemical_formula_sum 'C18 H24 N4 O4' _chemical_formula_weight 360.41 _chemical_absolute_configuration syn 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 P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 4.7957(14) _cell_length_b 19.605(6) _cell_length_c 9.913(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.076(4) _cell_angle_gamma 90.00 _cell_volume 917.7(5) _cell_formula_units_Z 2 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 3211 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 26.63 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.76 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.970 _exptl_absorpt_correction_T_max 0.983 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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_device 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10080 _diffrn_reflns_av_R_equivalents 0.0163 _diffrn_reflns_av_sigmaI/netI 0.0199 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4092 _reflns_number_gt 3811 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SAINT' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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^)+(0.0769P)^2^+0.1468P] 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 -0.5(13) _refine_ls_number_reflns 4092 _refine_ls_number_parameters 248 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0537 _refine_ls_R_factor_gt 0.0505 _refine_ls_wR_factor_ref 0.1377 _refine_ls_wR_factor_gt 0.1348 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.005 _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 0.3828(4) 0.13376(8) 0.32095(15) 0.0546(4) Uani 1 1 d . . . O2 O 0.0828(3) -0.01514(11) 0.2805(2) 0.0684(5) Uani 1 1 d . . . O3 O -0.0360(5) -0.01094(11) -0.1263(2) 0.0822(6) Uani 1 1 d . . . O4 O -0.0775(6) 0.30256(11) -0.0298(2) 0.0907(7) Uani 1 1 d . . . N1 N 0.3959(4) 0.06388(9) 0.49933(17) 0.0458(4) Uani 1 1 d . . . N2 N 0.4767(4) -0.01638(10) 0.18731(19) 0.0499(4) Uani 1 1 d . . . N3 N 0.1381(5) 0.07422(12) 0.0133(3) 0.0717(7) Uani 1 1 d . . . N4 N 0.0494(5) 0.21614(11) 0.1138(2) 0.0584(5) Uani 1 1 d . . . C1 C 0.3081(6) 0.03951(13) 0.6262(2) 0.0572(5) Uani 1 1 d . . . H1A H 0.1178 0.0546 0.6318 0.069 Uiso 1 1 calc R . . H1B H 0.4371 0.0553 0.7066 0.069 Uiso 1 1 calc R . . C2 C 0.3209(8) -0.03688(16) 0.6124(4) 0.0846(9) Uani 1 1 d . . . H2A H 0.3693 -0.0581 0.7019 0.102 Uiso 1 1 calc R . . H2B H 0.1396 -0.0546 0.5672 0.102 Uiso 1 1 calc R . . C3 C 0.5392(7) -0.05044(16) 0.5305(3) 0.0760(8) Uani 1 1 d . . . H3A H 0.5041 -0.0935 0.4825 0.091 Uiso 1 1 calc R . . H3B H 0.7248 -0.0521 0.5881 0.091 Uiso 1 1 calc R . . C4 C 0.5214(4) 0.00907(12) 0.4284(2) 0.0494(5) Uani 1 1 d . . . H4A H 0.7120 0.0222 0.4152 0.059 Uiso 1 1 calc R . . C5 C 0.3393(4) -0.00784(11) 0.2914(2) 0.0475(4) Uani 1 1 d . . . C6 C 0.3344(5) -0.03991(13) 0.0547(3) 0.0582(6) Uani 1 1 d . . . H6A H 0.2335 -0.0816 0.0679 0.070 Uiso 1 1 calc R . . H6B H 0.4772 -0.0513 0.0002 0.070 Uiso 1 1 calc R . . C7 C 0.1287(5) 0.00907(12) -0.0257(2) 0.0548(5) Uani 1 1 d . . . C8 C -0.0661(8) 0.12426(16) -0.0516(3) 0.0814(9) Uani 1 1 d . . . H8A H -0.2271 0.1006 -0.1040 0.098 Uiso 1 1 calc R . . H8B H 0.0203 0.1514 -0.1151 0.098 Uiso 1 1 calc R . . C9 C -0.1672(6) 0.17022(15) 0.0476(3) 0.0703(7) Uani 1 1 d . . . H9A H -0.3255 0.1967 0.0003 0.084 Uiso 1 1 calc R . . H9B H -0.2351 0.1430 0.1169 0.084 Uiso 1 1 calc R . . C10 C 0.0765(6) 0.27955(13) 0.0702(3) 0.0602(6) Uani 1 1 d . . . C11 C 0.3099(8) 0.32033(16) 0.1542(4) 0.0859(9) Uani 1 1 d . . . H11A H 0.4650 0.3245 0.1053 0.129 Uiso 1 1 calc R . . H11B H 0.3732 0.2976 0.2399 0.129 Uiso 1 1 calc R . . H11C H 0.2404 0.3649 0.1711 0.129 Uiso 1 1 calc R . . C12 C 0.3430(4) 0.12416(11) 0.4388(2) 0.0453(4) Uani 1 1 d . . . C13 C 0.2433(5) 0.18140(11) 0.5189(2) 0.0490(5) Uani 1 1 d . . . C14 C 0.0105(5) 0.21953(14) 0.4611(3) 0.0598(6) Uani 1 1 d . . . H14 H -0.0955 0.2068 0.3773 0.072 Uiso 1 1 calc R . . C15 C -0.0642(8) 0.27648(17) 0.5280(4) 0.0810(9) Uani 1 1 d . . . H15 H -0.2225 0.3016 0.4890 0.097 Uiso 1 1 calc R . . C16 C 0.0906(8) 0.29693(15) 0.6511(3) 0.0802(8) Uani 1 1 d . . . H16 H 0.0386 0.3357 0.6949 0.096 Uiso 1 1 calc R . . C17 C 0.3206(8) 0.25993(16) 0.7082(3) 0.0811(9) Uani 1 1 d . . . H17 H 0.4262 0.2736 0.7916 0.097 Uiso 1 1 calc R . . C18 C 0.4001(7) 0.20212(15) 0.6439(3) 0.0702(7) Uani 1 1 d . . . H18 H 0.5579 0.1772 0.6842 0.084 Uiso 1 1 calc R . . H2 H 0.651(6) -0.0150(12) 0.202(2) 0.040(5) Uiso 1 1 d . . . H3 H 0.256(7) 0.0851(18) 0.079(3) 0.071(9) Uiso 1 1 d . . . H4 H 0.139(6) 0.2049(15) 0.185(3) 0.056(7) Uiso 1 1 d . . . 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 0.0677(9) 0.0528(9) 0.0419(7) 0.0038(6) 0.0054(6) 0.0079(7) O2 0.0315(7) 0.0936(13) 0.0810(11) -0.0262(10) 0.0120(7) -0.0070(8) O3 0.1067(15) 0.0708(12) 0.0603(10) -0.0182(9) -0.0098(10) -0.0166(11) O4 0.135(2) 0.0585(11) 0.0699(12) 0.0146(10) -0.0063(12) 0.0162(12) N1 0.0464(9) 0.0479(9) 0.0424(8) 0.0006(7) 0.0053(7) 0.0019(7) N2 0.0314(8) 0.0552(10) 0.0633(10) -0.0141(9) 0.0088(7) -0.0002(7) N3 0.0706(14) 0.0585(12) 0.0750(15) -0.0163(11) -0.0177(12) -0.0024(10) N4 0.0687(12) 0.0487(10) 0.0522(10) 0.0054(8) -0.0051(9) 0.0025(9) C1 0.0704(15) 0.0582(13) 0.0427(11) 0.0034(9) 0.0094(9) -0.0037(11) C2 0.114(3) 0.0640(17) 0.0821(19) 0.0236(15) 0.0339(18) 0.0152(17) C3 0.0862(19) 0.0599(15) 0.0833(19) 0.0161(13) 0.0191(15) 0.0169(13) C4 0.0400(10) 0.0520(11) 0.0562(11) 0.0024(9) 0.0080(8) 0.0067(8) C5 0.0335(8) 0.0453(10) 0.0634(12) -0.0095(9) 0.0079(8) 0.0010(8) C6 0.0541(12) 0.0561(13) 0.0669(13) -0.0237(11) 0.0171(10) -0.0037(10) C7 0.0548(12) 0.0585(13) 0.0517(11) -0.0123(10) 0.0111(10) -0.0144(10) C8 0.098(2) 0.0627(15) 0.0698(16) -0.0068(13) -0.0243(15) 0.0006(15) C9 0.0608(15) 0.0562(14) 0.0861(18) 0.0072(12) -0.0087(12) -0.0015(11) C10 0.0840(17) 0.0469(11) 0.0493(12) 0.0026(9) 0.0108(11) 0.0107(11) C11 0.100(2) 0.0554(15) 0.100(2) -0.0024(14) 0.0101(18) -0.0116(15) C12 0.0412(10) 0.0484(11) 0.0424(9) -0.0002(8) -0.0030(7) -0.0016(8) C13 0.0587(12) 0.0428(11) 0.0445(10) -0.0018(8) 0.0063(9) -0.0019(9) C14 0.0615(13) 0.0597(13) 0.0564(13) -0.0062(10) 0.0056(10) 0.0055(11) C15 0.088(2) 0.0711(18) 0.085(2) -0.0070(15) 0.0177(16) 0.0231(16) C16 0.115(3) 0.0556(15) 0.0755(17) -0.0153(13) 0.0312(17) 0.0056(16) C17 0.118(3) 0.0672(17) 0.0545(14) -0.0168(12) 0.0042(15) -0.0074(17) C18 0.0867(18) 0.0662(16) 0.0510(13) -0.0067(11) -0.0064(12) 0.0061(13) _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 C12 1.230(3) . ? O2 C5 1.224(2) . ? O3 C7 1.223(3) . ? O4 C10 1.215(3) . ? N1 C12 1.330(3) . ? N1 C1 1.474(3) . ? N1 C4 1.470(3) . ? N2 C5 1.329(3) . ? N2 C6 1.446(3) . ? N3 C8 1.454(4) . ? N4 C10 1.330(3) . ? N4 C9 1.443(3) . ? C1 C2 1.506(4) . ? C2 C3 1.457(5) . ? C4 C3 1.537(4) . ? C5 C4 1.517(3) . ? C7 N3 1.333(3) . ? C7 C6 1.502(4) . ? C9 C8 1.477(5) . ? C10 C11 1.503(4) . ? C12 C13 1.501(3) . ? C13 C14 1.382(3) . ? C13 C18 1.393(3) . ? C14 C15 1.377(4) . ? C15 C16 1.373(5) . ? C16 C17 1.358(5) . ? C18 C17 1.386(4) . ? 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 C12 N1 121.03(19) . . ? O1 C12 C13 120.33(19) . . ? O2 C5 N2 123.0(2) . . ? O2 C5 C4 121.10(19) . . ? O3 C7 N3 121.9(3) . . ? O3 C7 C6 119.9(2) . . ? O4 C10 N4 122.2(3) . . ? O4 C10 C11 122.8(3) . . ? N1 C12 C13 118.60(18) . . ? N1 C4 C5 111.59(16) . . ? N1 C4 C3 102.72(19) . . ? N1 C1 C2 102.9(2) . . ? N2 C5 C4 115.89(17) . . ? N2 C6 C7 116.10(19) . . ? N3 C7 C6 118.2(2) . . ? N3 C8 C9 113.0(2) . . ? N4 C9 C8 112.9(3) . . ? N4 C10 C11 115.0(2) . . ? C1 N1 C4 111.92(18) . . ? C2 C3 C4 105.4(2) . . ? C3 C2 C1 106.1(3) . . ? C5 N2 C6 121.78(18) . . ? C5 C4 C3 112.4(2) . . ? C7 N3 C8 122.2(2) . . ? C10 N4 C9 122.6(2) . . ? C12 N1 C1 127.81(18) . . ? C12 N1 C4 119.71(17) . . ? C13 C14 C15 119.9(2) . . ? C14 C13 C18 118.8(2) . . ? C14 C13 C12 119.60(19) . . ? C16 C15 C14 121.3(3) . . ? C16 C17 C18 120.9(3) . . ? C17 C18 C13 119.9(3) . . ? C17 C16 C15 119.2(3) . . ? C18 C13 C12 121.1(2) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.269 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.040 # Attachment 'shrini1.cif' data_shrini1 _database_code_depnum_ccdc_archive 'CCDC 680779' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C21 H37 N5 O7 . H2O' _chemical_formula_sum 'C21 H39 N5 O8' _chemical_formula_weight 489.57 _chemical_absolute_configuration syn 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 P2(1)2(1)2(1) 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 9.056(5) _cell_length_b 9.842(4) _cell_length_c 29.153(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2598(2) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 1533 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 18.64 _exptl_crystal_description 'THIN PLATE' _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.252 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9653 _exptl_absorpt_correction_T_max 0.9981 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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_device 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15967 _diffrn_reflns_av_R_equivalents 0.0827 _diffrn_reflns_av_sigmaI/netI 0.0807 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4566 _reflns_number_gt 3295 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SAINT' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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^)+(0.0452P)^2^+0.8291P] 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 1(2) _refine_ls_number_reflns 4566 _refine_ls_number_parameters 347 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1032 _refine_ls_R_factor_gt 0.0711 _refine_ls_wR_factor_ref 0.1512 _refine_ls_wR_factor_gt 0.1383 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _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 0.5665(3) 0.6251(2) 0.98452(8) 0.0456(7) Uani 1 1 d . . . O2 O 0.3448(4) 0.7517(4) 0.89705(10) 0.0702(9) Uani 1 1 d . . . O3 O 0.5515(3) 0.8260(4) 0.86133(9) 0.0654(9) Uani 1 1 d . . . O4 O 0.3038(3) 0.4604(3) 1.04991(10) 0.0491(7) Uani 1 1 d . . . O5 O 0.3349(3) 0.1623(3) 0.96460(12) 0.0737(10) Uani 1 1 d . . . O6 O 0.6987(5) 0.3331(6) 0.81043(13) 0.140(2) Uani 1 1 d . . . O7 O 0.8874(3) 0.2287(3) 0.84483(11) 0.0704(9) Uani 1 1 d . . . O8 O 0.2131(4) 0.5457(4) 0.95329(15) 0.0853(11) Uani 1 1 d D . . N1 N 0.4671(3) 0.7115(3) 1.04842(10) 0.0372(7) Uani 1 1 d . . . N2 N 0.5263(4) 0.8607(3) 0.93513(10) 0.0460(8) Uani 1 1 d . . . H2 H 0.6087 0.9035 0.9325 0.055 Uiso 1 1 calc R . . N3 N 0.5272(3) 0.3621(3) 1.04857(10) 0.0407(8) Uani 1 1 d . . . H3 H 0.6199 0.3688 1.0545 0.049 Uiso 1 1 calc R . . N4 N 0.4955(4) 0.3324(4) 0.95407(12) 0.0494(9) Uani 1 1 d . . . N5 N 0.6662(4) 0.2146(5) 0.87457(14) 0.0649(12) Uani 1 1 d . . . C1 C 0.4002(6) 0.8191(5) 1.07705(14) 0.0490(11) Uani 1 1 d . . . C2 C 0.4433(6) 0.7770(5) 1.12441(14) 0.0681(14) Uani 1 1 d . . . H2A H 0.5380 0.8162 1.1327 0.082 Uiso 1 1 calc R . . H2B H 0.3700 0.8068 1.1465 0.082 Uiso 1 1 calc R . . C3 C 0.4527(6) 0.6263(4) 1.12368(13) 0.0608(12) Uani 1 1 d . . . H3A H 0.3565 0.5857 1.1288 0.073 Uiso 1 1 calc R . . H3B H 0.5206 0.5935 1.1469 0.073 Uiso 1 1 calc R . . C4 C 0.5096(4) 0.5939(4) 1.07535(11) 0.0391(9) Uani 1 1 d . . . H4A H 0.6173 0.5843 1.0757 0.047 Uiso 1 1 calc R . . C5 C 0.5028(4) 0.7204(4) 1.00410(13) 0.0391(9) Uani 1 1 d . . . C6 C 0.4601(6) 0.8487(4) 0.97942(14) 0.0463(10) Uani 1 1 d . . . C7 C 0.4644(5) 0.8079(4) 0.89778(13) 0.0465(10) Uani 1 1 d . . . C8 C 0.4966(6) 0.8041(5) 0.81433(14) 0.0657(14) Uani 1 1 d . . . C22 C 0.4590(9) 0.6583(6) 0.80731(18) 0.117(2) Uani 1 1 d . . . H22A H 0.5433 0.6031 0.8145 0.175 Uiso 1 1 calc R . . H22B H 0.4311 0.6439 0.7759 0.175 Uiso 1 1 calc R . . H22C H 0.3783 0.6339 0.8270 0.175 Uiso 1 1 calc R . . C23 C 0.6258(7) 0.8495(9) 0.78553(16) 0.119(3) Uani 1 1 d . . . H23A H 0.6514 0.9412 0.7934 0.178 Uiso 1 1 calc R . . H23B H 0.5996 0.8449 0.7537 0.178 Uiso 1 1 calc R . . H23C H 0.7087 0.7911 0.7912 0.178 Uiso 1 1 calc R . . C24 C 0.3669(7) 0.8949(6) 0.80566(16) 0.0883(18) Uani 1 1 d . . . H24A H 0.2843 0.8645 0.8236 0.133 Uiso 1 1 calc R . . H24B H 0.3416 0.8921 0.7737 0.133 Uiso 1 1 calc R . . H24C H 0.3915 0.9864 0.8142 0.133 Uiso 1 1 calc R . . C12 C 0.4383(4) 0.4661(4) 1.05640(12) 0.0356(9) Uani 1 1 d . . . C13 C 0.4679(5) 0.2366(4) 1.03004(15) 0.0509(11) Uani 1 1 d . . . C14 C 0.4260(5) 0.2431(4) 0.97980(16) 0.0481(11) Uani 1 1 d . . . C15 C 0.4609(6) 0.3524(5) 0.90613(14) 0.0640(13) Uani 1 1 d . . . H15A H 0.5099 0.4340 0.8953 0.077 Uiso 1 1 calc R . . H15B H 0.3553 0.3657 0.9029 0.077 Uiso 1 1 calc R . . C16 C 0.5085(5) 0.2325(6) 0.87637(16) 0.0754(16) Uani 1 1 d . . . H16A H 0.4639 0.1501 0.8883 0.090 Uiso 1 1 calc R . . H16B H 0.4717 0.2461 0.8455 0.090 Uiso 1 1 calc R . . C17 C 0.7472(6) 0.2661(6) 0.84061(16) 0.0664(14) Uani 1 1 d . . . C18 C 0.9998(5) 0.2709(5) 0.81181(16) 0.0626(12) Uani 1 1 d . . . C27 C 1.1351(7) 0.2059(9) 0.8292(2) 0.137(3) Uani 1 1 d . . . H27A H 1.1550 0.2378 0.8597 0.205 Uiso 1 1 calc R . . H27B H 1.2165 0.2285 0.8096 0.205 Uiso 1 1 calc R . . H27C H 1.1220 0.1092 0.8297 0.205 Uiso 1 1 calc R . . C26 C 0.9635(8) 0.2146(12) 0.7673(2) 0.194(5) Uani 1 1 d . . . H26A H 1.0515 0.1805 0.7531 0.291 Uiso 1 1 calc R . . H26B H 0.9209 0.2841 0.7484 0.291 Uiso 1 1 calc R . . H26C H 0.8939 0.1419 0.7711 0.291 Uiso 1 1 calc R . . C25 C 1.0146(13) 0.4178(6) 0.8124(4) 0.227(6) Uani 1 1 d . . . H25A H 0.9524 0.4549 0.8360 0.340 Uiso 1 1 calc R . . H25B H 0.9856 0.4540 0.7832 0.340 Uiso 1 1 calc R . . H25C H 1.1155 0.4417 0.8185 0.340 Uiso 1 1 calc R . . H1B H 0.432(4) 0.900(4) 1.0678(12) 0.037(11) Uiso 1 1 d . . . H1A H 0.287(6) 0.833(5) 1.0688(16) 0.089(17) Uiso 1 1 d . . . H4 H 0.541(4) 0.394(3) 0.9655(11) 0.026(10) Uiso 1 1 d . . . H5 H 0.713(5) 0.166(5) 0.8956(16) 0.069(15) Uiso 1 1 d . . . H6A H 0.361(4) 0.847(3) 0.9763(10) 0.020(9) Uiso 1 1 d . . . H6B H 0.499(4) 0.928(4) 0.9976(12) 0.048(11) Uiso 1 1 d . . . H13A H 0.541(4) 0.172(4) 1.0325(11) 0.032(10) Uiso 1 1 d . . . H13B H 0.375(2) 0.205(3) 1.0465(7) 0.040(10) Uiso 1 1 d . . . H16 H 0.2603 0.5317 0.9772 0.66(19) Uiso 1 1 d RD . . H17 H 0.2728 0.5918 0.9386 0.8(3) Uiso 1 1 d RD . . 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 0.0567(18) 0.0371(14) 0.0431(14) -0.0012(12) 0.0122(13) -0.0012(14) O2 0.058(2) 0.094(2) 0.0593(19) -0.0052(18) -0.0023(16) -0.028(2) O3 0.0511(19) 0.106(2) 0.0387(16) 0.0029(16) 0.0005(14) -0.0081(19) O4 0.0321(17) 0.0446(16) 0.0706(19) 0.0022(14) 0.0030(15) -0.0016(14) O5 0.0449(19) 0.0575(19) 0.119(3) -0.0186(19) -0.0137(19) -0.0055(17) O6 0.110(3) 0.242(6) 0.070(2) 0.063(3) 0.020(2) 0.108(4) O7 0.049(2) 0.087(2) 0.075(2) 0.0254(19) -0.0007(17) 0.0114(18) O8 0.058(2) 0.084(2) 0.114(3) 0.003(2) -0.005(2) 0.009(2) N1 0.0454(19) 0.0327(16) 0.0334(16) -0.0009(13) 0.0034(15) -0.0008(15) N2 0.050(2) 0.0513(19) 0.0370(18) 0.0048(15) -0.0022(16) -0.0146(18) N3 0.0290(17) 0.0343(16) 0.0589(19) 0.0007(15) -0.0002(16) 0.0055(15) N4 0.052(2) 0.037(2) 0.059(2) -0.0096(18) -0.0039(19) -0.0066(19) N5 0.050(3) 0.086(3) 0.058(3) 0.008(2) -0.008(2) 0.017(2) C1 0.058(3) 0.040(3) 0.049(3) -0.008(2) 0.006(2) -0.001(2) C2 0.095(4) 0.061(3) 0.048(3) -0.011(2) 0.017(3) -0.007(3) C3 0.081(3) 0.061(3) 0.040(2) 0.000(2) 0.000(2) 0.006(3) C4 0.034(2) 0.047(2) 0.037(2) 0.0032(17) -0.0033(17) 0.002(2) C5 0.039(2) 0.035(2) 0.043(2) -0.0050(17) -0.0022(18) -0.0011(18) C6 0.054(3) 0.042(2) 0.043(2) -0.0003(19) 0.000(2) -0.007(2) C7 0.049(3) 0.049(2) 0.042(2) 0.0020(19) -0.003(2) -0.001(2) C8 0.073(3) 0.088(4) 0.036(2) -0.007(2) -0.001(2) 0.013(3) C22 0.195(8) 0.086(4) 0.070(4) -0.023(3) -0.012(4) 0.020(5) C23 0.096(5) 0.218(8) 0.042(3) 0.016(4) 0.015(3) 0.008(5) C24 0.101(5) 0.109(4) 0.056(3) -0.004(3) -0.023(3) 0.029(4) C12 0.030(2) 0.040(2) 0.037(2) 0.0087(17) 0.0030(17) 0.0010(19) C13 0.045(3) 0.034(2) 0.074(3) 0.004(2) 0.012(2) 0.001(2) C14 0.033(2) 0.031(2) 0.080(3) -0.009(2) 0.000(2) 0.004(2) C15 0.062(3) 0.071(3) 0.060(3) -0.007(2) -0.011(2) 0.018(3) C16 0.051(3) 0.103(4) 0.072(3) -0.031(3) -0.019(2) 0.029(3) C17 0.066(3) 0.089(4) 0.044(3) 0.004(3) -0.002(3) 0.035(3) C18 0.063(3) 0.064(3) 0.061(3) 0.008(2) 0.002(2) 0.003(3) C27 0.058(4) 0.193(8) 0.159(7) 0.089(6) 0.007(4) 0.000(5) C26 0.081(5) 0.385(15) 0.116(6) -0.128(8) 0.003(4) 0.031(8) C25 0.238(12) 0.058(4) 0.385(15) 0.001(6) 0.187(12) -0.027(6) _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 1.240(4) . ? O2 C7 1.216(5) . ? O3 C7 1.335(5) . ? O3 C8 1.473(5) . ? O4 C12 1.234(4) . ? O5 C14 1.229(5) . ? O6 C17 1.184(5) . ? O7 C17 1.327(5) . ? O7 C18 1.461(5) . ? N1 C5 1.335(5) . ? N1 C4 1.451(4) . ? N1 C1 1.478(5) . ? N2 C7 1.331(5) . ? N2 C6 1.428(5) . ? N3 C12 1.322(5) . ? N3 C13 1.451(5) . ? N4 C14 1.316(5) . ? N4 C15 1.446(5) . ? N5 C17 1.333(6) . ? N5 C16 1.440(6) . ? C1 C2 1.494(6) . ? C2 C3 1.486(6) . ? C3 C4 1.534(5) . ? C4 C12 1.518(5) . ? C5 C6 1.504(5) . ? C8 C22 1.490(8) . ? C8 C24 1.498(7) . ? C8 C23 1.507(7) . ? C13 C14 1.514(6) . ? C15 C16 1.527(6) . ? C18 C26 1.448(8) . ? C18 C25 1.452(8) . ? C18 C27 1.473(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 C7 O3 C8 121.4(4) . . ? C17 O7 C18 121.8(4) . . ? C5 N1 C4 120.8(3) . . ? C5 N1 C1 126.8(3) . . ? C4 N1 C1 112.0(3) . . ? C7 N2 C6 122.1(4) . . ? C12 N3 C13 119.9(3) . . ? C14 N4 C15 122.6(4) . . ? C17 N5 C16 121.8(4) . . ? N1 C1 C2 102.5(4) . . ? C3 C2 C1 106.1(4) . . ? C2 C3 C4 103.9(3) . . ? N1 C4 C12 110.6(3) . . ? N1 C4 C3 104.0(3) . . ? C12 C4 C3 111.3(3) . . ? O1 C5 N1 120.6(3) . . ? O1 C5 C6 122.3(3) . . ? N1 C5 C6 117.1(3) . . ? N2 C6 C5 113.2(4) . . ? O2 C7 N2 124.5(4) . . ? O2 C7 O3 124.9(4) . . ? N2 C7 O3 110.5(4) . . ? O3 C8 C22 110.2(4) . . ? O3 C8 C24 109.5(4) . . ? C22 C8 C24 111.8(5) . . ? O3 C8 C23 102.3(4) . . ? C22 C8 C23 112.7(5) . . ? C24 C8 C23 109.8(5) . . ? O4 C12 N3 122.6(4) . . ? O4 C12 C4 120.9(3) . . ? N3 C12 C4 116.5(3) . . ? N3 C13 C14 114.6(3) . . ? O5 C14 N4 123.2(5) . . ? O5 C14 C13 119.3(4) . . ? N4 C14 C13 117.4(4) . . ? N4 C15 C16 112.5(4) . . ? N5 C16 C15 113.3(4) . . ? O6 C17 O7 125.3(5) . . ? O6 C17 N5 124.1(5) . . ? O7 C17 N5 110.6(4) . . ? C26 C18 C25 114.4(8) . . ? C26 C18 O7 108.8(5) . . ? C25 C18 O7 109.8(5) . . ? C26 C18 C27 109.3(6) . . ? C25 C18 C27 110.6(7) . . ? O7 C18 C27 103.2(4) . . ? 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 N1 C1 C2 -157.1(4) . . . . ? C4 N1 C1 C2 15.6(5) . . . . ? N1 C1 C2 C3 -30.7(5) . . . . ? C1 C2 C3 C4 34.3(6) . . . . ? C5 N1 C4 C12 -62.2(4) . . . . ? C1 N1 C4 C12 124.6(4) . . . . ? C5 N1 C4 C3 178.2(3) . . . . ? C1 N1 C4 C3 5.0(5) . . . . ? C2 C3 C4 N1 -23.8(5) . . . . ? C2 C3 C4 C12 -142.9(4) . . . . ? C4 N1 C5 O1 3.7(5) . . . . ? C1 N1 C5 O1 175.8(4) . . . . ? C4 N1 C5 C6 -177.3(4) . . . . ? C1 N1 C5 C6 -5.3(6) . . . . ? C7 N2 C6 C5 87.2(5) . . . . ? O1 C5 C6 N2 -12.2(6) . . . . ? N1 C5 C6 N2 168.8(3) . . . . ? C6 N2 C7 O2 4.0(6) . . . . ? C6 N2 C7 O3 -176.4(4) . . . . ? C8 O3 C7 O2 12.9(7) . . . . ? C8 O3 C7 N2 -166.6(4) . . . . ? C7 O3 C8 C22 -65.3(6) . . . . ? C7 O3 C8 C24 58.2(6) . . . . ? C7 O3 C8 C23 174.6(5) . . . . ? C13 N3 C12 O4 2.3(6) . . . . ? C13 N3 C12 C4 -179.4(3) . . . . ? N1 C4 C12 O4 -52.5(4) . . . . ? C3 C4 C12 O4 62.6(5) . . . . ? N1 C4 C12 N3 129.2(3) . . . . ? C3 C4 C12 N3 -115.7(4) . . . . ? C12 N3 C13 C14 73.3(5) . . . . ? C15 N4 C14 O5 5.9(6) . . . . ? C15 N4 C14 C13 -177.3(4) . . . . ? N3 C13 C14 O5 -156.9(4) . . . . ? N3 C13 C14 N4 26.1(5) . . . . ? C14 N4 C15 C16 -70.2(5) . . . . ? C17 N5 C16 C15 -95.6(5) . . . . ? N4 C15 C16 N5 -65.8(6) . . . . ? C18 O7 C17 O6 1.3(8) . . . . ? C18 O7 C17 N5 179.7(4) . . . . ? C16 N5 C17 O6 2.5(9) . . . . ? C16 N5 C17 O7 -175.9(4) . . . . ? C17 O7 C18 C26 -63.1(7) . . . . ? C17 O7 C18 C25 62.8(8) . . . . ? C17 O7 C18 C27 -179.2(5) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.188 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.041