# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Al-sehemi, Abdullah G.' 'Atkinson, Robert S.' 'Fawcett, John' _publ_contact_author_name 'Dr Robert S Atkinson' _publ_contact_author_address ; Dr Robert S Atkinson Department of Chemistry Leicester University Leicester LE1 7RH UNITED KINGDOM ; _publ_contact_author_email 'CHEMADMISS@LE.AC.UK' _publ_section_title ; Title Kinetic resolution of amines with enantiopure 3-N,N-diacylaminoquinazolin-4(3H)-ones ; data_10a _database_code_CSD 167260 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H29 N3 O7' _chemical_formula_weight 555.57 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 11.315(3) _cell_length_b 14.210(2) _cell_length_c 17.368(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2792.4(11) _cell_formula_units_Z 4 _cell_measurement_temperature 190(2) _cell_measurement_reflns_used 41 _cell_measurement_theta_min 5.40 _cell_measurement_theta_max 12.45 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.31 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type 'not applied' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 190(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 'Siemens P4 diffractometer' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <2 _diffrn_reflns_number 3891 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0372 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3692 _reflns_number_gt 2817 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XSCANS (Fait, 1991)' _computing_cell_refinement 'XSCANS (Fait, 1991)' _computing_data_reduction 'XSCANS (Fait, 1991)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0676P)^2^+1.9182P] 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 0.0128(15) _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 0.9(19) _refine_ls_number_reflns 3692 _refine_ls_number_parameters 342 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0784 _refine_ls_R_factor_gt 0.0537 _refine_ls_wR_factor_ref 0.1462 _refine_ls_wR_factor_gt 0.1270 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.000 _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 0.1243(2) 0.2368(2) 0.67648(17) 0.0449(7) Uani 1 1 d . . . O2 O 0.1359(2) 0.3472(2) 0.86275(15) 0.0404(7) Uani 1 1 d . . . O3 O 0.3192(3) 0.2525(2) 0.92988(15) 0.0416(7) Uani 1 1 d . . . O4 O 0.4009(3) 0.3934(2) 0.90802(18) 0.0539(8) Uani 1 1 d . . . O5 O 0.1690(3) 0.4473(2) 0.64789(16) 0.0435(7) Uani 1 1 d . . . O6 O 0.1942(2) 0.53588(19) 0.82809(15) 0.0376(7) Uani 1 1 d . . . O7 O 0.0452(3) 0.5552(3) 0.91170(17) 0.0533(9) Uani 1 1 d . . . N1 N 0.4672(3) 0.2870(2) 0.6183(2) 0.0380(8) Uani 1 1 d . . . N2 N 0.2414(3) 0.3663(2) 0.75061(17) 0.0320(7) Uani 1 1 d . . . N3 N 0.3002(3) 0.3104(2) 0.69665(17) 0.0304(7) Uani 1 1 d . . . C1 C 0.4787(3) 0.4103(3) 0.7160(2) 0.0339(9) Uani 1 1 d . . . H1B H 0.4391 0.4163 0.7660 0.041 Uiso 1 1 calc R . . C2 C 0.4167(3) 0.3313(3) 0.6739(2) 0.0319(9) Uani 1 1 d . . . C4 C 0.2271(3) 0.2454(3) 0.6573(2) 0.0336(9) Uani 1 1 d . . . C5 C 0.2878(4) 0.1930(3) 0.5975(2) 0.0337(9) Uani 1 1 d . . . C6 C 0.2294(4) 0.1212(3) 0.5578(2) 0.0456(11) Uani 1 1 d . . . H6A H 0.1515 0.1063 0.5695 0.055 Uiso 1 1 calc R . . C7 C 0.2892(4) 0.0728(3) 0.5007(3) 0.0510(12) Uani 1 1 d . . . H7A H 0.2524 0.0234 0.4750 0.061 Uiso 1 1 calc R . . C8 C 0.4043(5) 0.0980(3) 0.4818(3) 0.0527(12) Uani 1 1 d . . . H8A H 0.4434 0.0654 0.4429 0.063 Uiso 1 1 calc R . . C9 C 0.4615(4) 0.1698(3) 0.5191(3) 0.0470(11) Uani 1 1 d . . . H9A H 0.5375 0.1872 0.5044 0.056 Uiso 1 1 calc R . . C10 C 0.4044(4) 0.2168(3) 0.5795(2) 0.0352(9) Uani 1 1 d . . . C11 C 0.61154(18) 0.3936(2) 0.73370(15) 0.0366(9) Uani 1 1 d G . . C12 C 0.6491(2) 0.4148(2) 0.80793(14) 0.0470(11) Uani 1 1 d G . . H12A H 0.5965 0.4409 0.8431 0.056 Uiso 1 1 calc R . . C13 C 0.7652(2) 0.3968(2) 0.82960(13) 0.0559(13) Uani 1 1 d G . . H13A H 0.7902 0.4110 0.8793 0.067 Uiso 1 1 calc R . . C14 C 0.84374(19) 0.3577(2) 0.77704(18) 0.0558(13) Uani 1 1 d G . . H14A H 0.9214 0.3457 0.7915 0.067 Uiso 1 1 calc R . . C15 C 0.8062(2) 0.3366(2) 0.70282(16) 0.0559(13) Uani 1 1 d G . . H15A H 0.8588 0.3105 0.6677 0.067 Uiso 1 1 calc R . . C16 C 0.6901(2) 0.3546(2) 0.68115(12) 0.0475(11) Uani 1 1 d G . . H16A H 0.6650 0.3404 0.6315 0.057 Uiso 1 1 calc R . . C17 C 0.4575(2) 0.50339(14) 0.67335(14) 0.0344(9) Uani 1 1 d G . . C18 C 0.4187(3) 0.58065(18) 0.71547(12) 0.0442(11) Uani 1 1 d G . . H18A H 0.4090 0.5758 0.7685 0.053 Uiso 1 1 calc R . . C19 C 0.3947(3) 0.66516(15) 0.67834(18) 0.0555(13) Uani 1 1 d G . . H19A H 0.3688 0.7168 0.7065 0.067 Uiso 1 1 calc R . . C20 C 0.4093(3) 0.67241(14) 0.59910(18) 0.0532(12) Uani 1 1 d G . . H20A H 0.3932 0.7290 0.5743 0.064 Uiso 1 1 calc R . . C21 C 0.4480(3) 0.59515(19) 0.55698(12) 0.0490(11) Uani 1 1 d G . . H21A H 0.4578 0.6000 0.5040 0.059 Uiso 1 1 calc R . . C22 C 0.4721(2) 0.51064(15) 0.59411(14) 0.0390(10) Uani 1 1 d G . . H22A H 0.4980 0.4590 0.5659 0.047 Uiso 1 1 calc R . . C23 C 0.2180(3) 0.3226(3) 0.8227(2) 0.0329(9) Uani 1 1 d . . . C24 C 0.3013(4) 0.2442(3) 0.8473(2) 0.0352(9) Uani 1 1 d . . . H24A H 0.3770 0.2504 0.8203 0.042 Uiso 1 1 calc R . . C25 C 0.2513(4) 0.1471(3) 0.8351(3) 0.0508(12) Uani 1 1 d . . . H25A H 0.3086 0.1010 0.8506 0.076 Uiso 1 1 calc R . . H25B H 0.2327 0.1387 0.7816 0.076 Uiso 1 1 calc R . . H25C H 0.1809 0.1399 0.8653 0.076 Uiso 1 1 calc R . . C26 C 0.3750(4) 0.3315(4) 0.9515(3) 0.0472(11) Uani 1 1 d . . . C27 C 0.3995(5) 0.3319(4) 1.0361(2) 0.0651(15) Uani 1 1 d . . . H27A H 0.4389 0.3894 1.0497 0.098 Uiso 1 1 calc R . . H27B H 0.4489 0.2793 1.0489 0.098 Uiso 1 1 calc R . . H27C H 0.3263 0.3274 1.0638 0.098 Uiso 1 1 calc R . . C28 C 0.1724(3) 0.4391(3) 0.7173(2) 0.0347(9) Uani 1 1 d . . . C29 C 0.1088(4) 0.5073(3) 0.7703(2) 0.0354(9) Uani 1 1 d . . . H29A H 0.0425 0.4752 0.7953 0.043 Uiso 1 1 calc R . . C31 C 0.1487(4) 0.5606(3) 0.8973(3) 0.0425(10) Uani 1 1 d . . . C32 C 0.2425(5) 0.5954(4) 0.9497(3) 0.0620(14) Uani 1 1 d . . . H32A H 0.2081 0.6125 0.9982 0.093 Uiso 1 1 calc R . . H32B H 0.2800 0.6494 0.9272 0.093 Uiso 1 1 calc R . . H32C H 0.3001 0.5467 0.9575 0.093 Uiso 1 1 calc R . . C30 C 0.0642(4) 0.5925(3) 0.7281(3) 0.0520(12) Uiso 1 1 d . . . H30A H 0.0247 0.6336 0.7636 0.078 Uiso 1 1 calc R . . H30B H 0.0098 0.5732 0.6887 0.078 Uiso 1 1 calc R . . H30C H 0.1295 0.6250 0.7050 0.078 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0329(15) 0.0535(17) 0.0482(17) -0.0073(16) 0.0059(14) -0.0121(14) O2 0.0348(15) 0.0492(16) 0.0373(14) 0.0062(14) 0.0044(13) 0.0077(14) O3 0.0413(16) 0.0537(17) 0.0299(14) 0.0028(14) -0.0041(13) 0.0016(16) O4 0.055(2) 0.0588(19) 0.0477(18) -0.0070(17) 0.0001(17) -0.0117(18) O5 0.0462(17) 0.0516(17) 0.0328(15) 0.0017(13) -0.0029(14) 0.0081(16) O6 0.0340(14) 0.0412(15) 0.0377(15) -0.0066(13) 0.0003(14) -0.0023(13) O7 0.0401(17) 0.079(2) 0.0408(17) -0.0004(17) 0.0065(15) 0.0129(18) N1 0.0307(17) 0.0408(18) 0.0426(19) -0.0030(16) 0.0061(16) 0.0016(16) N2 0.0299(16) 0.0346(16) 0.0315(16) -0.0031(14) 0.0029(15) 0.0004(15) N3 0.0243(15) 0.0354(16) 0.0315(16) -0.0012(14) 0.0012(14) -0.0009(14) C1 0.0275(19) 0.039(2) 0.035(2) -0.0018(18) 0.0021(18) -0.0041(17) C2 0.0270(18) 0.0341(19) 0.035(2) 0.0052(18) 0.0009(17) 0.0003(17) C4 0.029(2) 0.038(2) 0.033(2) -0.0006(18) -0.0007(17) -0.0047(18) C5 0.034(2) 0.035(2) 0.0324(19) 0.0022(17) -0.0034(17) -0.0027(18) C6 0.047(3) 0.046(2) 0.044(2) -0.004(2) -0.001(2) -0.003(2) C7 0.055(3) 0.047(3) 0.051(3) -0.012(2) -0.007(2) -0.004(2) C8 0.054(3) 0.055(3) 0.049(3) -0.018(2) -0.003(2) 0.012(3) C9 0.039(2) 0.056(3) 0.046(2) -0.011(2) 0.002(2) 0.010(2) C10 0.033(2) 0.035(2) 0.038(2) 0.0008(18) -0.0036(19) 0.0017(18) C11 0.033(2) 0.034(2) 0.043(2) 0.0060(19) -0.006(2) -0.0067(18) C12 0.046(2) 0.043(2) 0.052(3) -0.005(2) -0.014(2) -0.008(2) C13 0.049(3) 0.052(3) 0.067(3) -0.006(3) -0.024(3) -0.006(2) C14 0.041(2) 0.047(3) 0.080(3) 0.011(3) -0.021(3) -0.013(2) C15 0.034(2) 0.065(3) 0.069(3) 0.008(3) 0.003(2) -0.006(2) C16 0.031(2) 0.063(3) 0.048(2) 0.011(2) 0.000(2) -0.004(2) C17 0.0244(18) 0.036(2) 0.043(2) -0.0021(19) 0.0017(19) -0.0034(17) C18 0.037(2) 0.040(2) 0.056(3) -0.006(2) 0.009(2) -0.006(2) C19 0.045(3) 0.035(2) 0.087(4) -0.011(3) 0.010(3) -0.005(2) C20 0.041(3) 0.035(2) 0.084(4) 0.008(3) -0.004(3) -0.003(2) C21 0.051(3) 0.047(2) 0.050(3) 0.009(2) -0.006(2) -0.007(2) C22 0.042(2) 0.037(2) 0.039(2) -0.0012(19) 0.000(2) 0.000(2) C23 0.032(2) 0.034(2) 0.0330(19) 0.0013(17) -0.0004(19) -0.0045(18) C24 0.0289(19) 0.043(2) 0.0336(19) 0.0030(18) -0.0020(17) 0.0019(19) C25 0.054(3) 0.042(2) 0.057(3) 0.004(2) -0.006(2) 0.002(2) C26 0.038(2) 0.063(3) 0.040(2) -0.003(2) -0.001(2) 0.004(2) C27 0.062(3) 0.095(4) 0.038(2) -0.005(3) -0.013(2) -0.002(3) C28 0.0264(18) 0.042(2) 0.036(2) -0.0004(18) 0.0001(18) -0.0018(19) C29 0.032(2) 0.042(2) 0.0328(19) 0.0002(18) -0.0065(18) 0.0025(19) C31 0.043(3) 0.045(2) 0.039(2) -0.005(2) 0.003(2) 0.012(2) C32 0.060(3) 0.072(3) 0.054(3) -0.024(3) -0.007(3) 0.001(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 C4 1.216(5) . ? O2 C23 1.211(5) . ? O3 C26 1.341(6) . ? O3 C24 1.454(5) . ? O4 C26 1.196(5) . ? O5 C28 1.212(5) . ? O6 C31 1.354(5) . ? O6 C29 1.451(5) . ? O7 C31 1.199(5) . ? N1 C2 1.286(5) . ? N1 C10 1.398(5) . ? N2 N3 1.397(4) . ? N2 C28 1.420(5) . ? N2 C23 1.423(5) . ? N3 C2 1.407(5) . ? N3 C4 1.416(5) . ? C1 C2 1.513(6) . ? C1 C17 1.536(4) . ? C1 C11 1.552(4) . ? C4 C5 1.451(6) . ? C5 C10 1.397(6) . ? C5 C6 1.398(6) . ? C6 C7 1.384(6) . ? C7 C8 1.390(7) . ? C8 C9 1.371(6) . ? C9 C10 1.403(6) . ? C11 C12 1.3900 . ? C11 C16 1.3900 . ? C12 C13 1.3900 . ? C13 C14 1.3900 . ? C14 C15 1.3900 . ? C15 C16 1.3900 . ? C17 C18 1.3900 . ? C17 C22 1.3900 . ? C18 C19 1.3900 . ? C19 C20 1.3900 . ? C20 C21 1.3900 . ? C21 C22 1.3900 . ? C23 C24 1.521(5) . ? C24 C25 1.506(6) . ? C26 C27 1.494(6) . ? C28 C29 1.517(6) . ? C29 C30 1.503(6) . ? C31 C32 1.482(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 C26 O3 C24 114.2(3) . . ? C31 O6 C29 115.7(3) . . ? C2 N1 C10 119.0(3) . . ? N3 N2 C28 113.8(3) . . ? N3 N2 C23 115.6(3) . . ? C28 N2 C23 125.0(3) . . ? N2 N3 C2 121.0(3) . . ? N2 N3 C4 114.6(3) . . ? C2 N3 C4 123.3(3) . . ? C2 C1 C17 109.4(3) . . ? C2 C1 C11 115.6(3) . . ? C17 C1 C11 112.2(3) . . ? N1 C2 N3 121.6(4) . . ? N1 C2 C1 121.3(3) . . ? N3 C2 C1 117.0(3) . . ? O1 C4 N3 119.5(4) . . ? O1 C4 C5 126.7(4) . . ? N3 C4 C5 113.8(3) . . ? C10 C5 C6 120.8(4) . . ? C10 C5 C4 118.9(4) . . ? C6 C5 C4 120.3(4) . . ? C7 C6 C5 119.1(4) . . ? C6 C7 C8 119.9(5) . . ? C9 C8 C7 121.5(5) . . ? C8 C9 C10 119.4(4) . . ? C5 C10 N1 123.0(4) . . ? C5 C10 C9 119.2(4) . . ? N1 C10 C9 117.8(4) . . ? C12 C11 C16 120.0 . . ? C12 C11 C1 116.5(2) . . ? C16 C11 C1 123.4(2) . . ? C11 C12 C13 120.0 . . ? C14 C13 C12 120.0 . . ? C13 C14 C15 120.0 . . ? C14 C15 C16 120.0 . . ? C15 C16 C11 120.0 . . ? C18 C17 C22 120.0 . . ? C18 C17 C1 118.4(2) . . ? C22 C17 C1 121.6(2) . . ? C17 C18 C19 120.0 . . ? C18 C19 C20 120.0 . . ? C21 C20 C19 120.0 . . ? C20 C21 C22 120.0 . . ? C21 C22 C17 120.0 . . ? O2 C23 N2 121.5(4) . . ? O2 C23 C24 121.7(4) . . ? N2 C23 C24 116.8(3) . . ? O3 C24 C25 105.4(3) . . ? O3 C24 C23 107.7(3) . . ? C25 C24 C23 113.5(3) . . ? O4 C26 O3 123.6(4) . . ? O4 C26 C27 124.9(5) . . ? O3 C26 C27 111.5(4) . . ? O5 C28 N2 119.4(4) . . ? O5 C28 C29 121.9(4) . . ? N2 C28 C29 118.6(3) . . ? O6 C29 C30 109.6(3) . . ? O6 C29 C28 106.4(3) . . ? C30 C29 C28 112.2(3) . . ? O7 C31 O6 122.7(4) . . ? O7 C31 C32 126.3(4) . . ? O6 C31 C32 111.0(4) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.230 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.051 data_15 _database_code_CSD 167261 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C27 H35 N3 O4 Si' _chemical_formula_weight 493.67 _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' 'Si' 'Si' 0.0817 0.0704 '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 9.649(2) _cell_length_b 9.283(6) _cell_length_c 15.152(5) _cell_angle_alpha 90.00 _cell_angle_beta 96.690(10) _cell_angle_gamma 90.00 _cell_volume 1347.9(10) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 22 _cell_measurement_theta_min 5.2 _cell_measurement_theta_max 12.12 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.216 _exptl_crystal_density_method ? _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_type 'not applied' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 'Siemens P4 Diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 3369 _diffrn_reflns_av_R_equivalents 0.0203 _diffrn_reflns_av_sigmaI/netI 0.0509 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2842 _reflns_number_observed 2231 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'XSCANS (Fait, 1991)' _computing_cell_refinement 'XSCANS (Fait, 1991)' _computing_data_reduction 'XSCANS (Fait, 1991)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'SHELXL-96 (Sheldrick, 1996)' _computing_publication_material 'SHELXL-96 (Sheldrick, 1996)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 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^)+(0.0385P)^2^+0.6550P] 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 'riding model' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0022(12) _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 0.13(22) _refine_ls_number_reflns 2842 _refine_ls_number_parameters 316 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0698 _refine_ls_R_factor_obs 0.0450 _refine_ls_wR_factor_all 0.0994 _refine_ls_wR_factor_obs 0.0883 _refine_ls_goodness_of_fit_all 1.031 _refine_ls_goodness_of_fit_obs 1.050 _refine_ls_restrained_S_all 1.031 _refine_ls_restrained_S_obs 1.050 _refine_ls_shift/esd_max 0.002 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Si1 Si 0.48944(11) 0.3152 0.28477(7) 0.0267(3) Uani 1 d . . O1 O -0.0829(3) 0.0904(4) 0.1312(2) 0.0360(8) Uani 1 d . . O2 O 0.3506(3) 0.4058(3) 0.2380(2) 0.0255(7) Uani 1 d . . O3 O -0.0935(3) 0.4178(4) 0.0972(2) 0.0446(9) Uani 1 d . . O4 O 0.2434(3) 0.0862(4) 0.1266(2) 0.0320(7) Uani 1 d . . N1 N 0.1132(3) 0.2627(4) 0.3592(2) 0.0253(8) Uani 1 d . . N2 N 0.1068(3) 0.2890(4) 0.1203(2) 0.0246(9) Uani 1 d . . N3 N 0.0714(3) 0.2480(4) 0.2040(2) 0.0247(8) Uani 1 d . . C1 C 0.2288(4) 0.4402(5) 0.2792(3) 0.0255(10) Uani 1 d . . H1B H 0.2611(4) 0.4646(5) 0.3411(3) 0.031 Uiso 1 calc R . C2 C 0.1342(4) 0.3100(6) 0.2818(2) 0.0252(9) Uani 1 d . . C3 C 0.1575(4) 0.5753(5) 0.2374(3) 0.0285(10) Uani 1 d . . H3A H 0.1352(4) 0.5581(5) 0.1735(3) 0.034 Uiso 1 calc R . C4 C -0.0266(4) 0.1343(5) 0.2014(3) 0.0284(11) Uani 1 d . . C5 C -0.0510(4) 0.0838(5) 0.2898(3) 0.0280(10) Uani 1 d . . C6 C -0.1450(5) -0.0283(5) 0.2983(3) 0.0338(11) Uani 1 d . . H6A H -0.1954(5) -0.0684(5) 0.2482(3) 0.041 Uiso 1 calc R . C7 C -0.1624(5) -0.0788(6) 0.3818(3) 0.0404(12) Uani 1 d . . H7A H -0.2249(5) -0.1533(6) 0.3882(3) 0.048 Uiso 1 calc R . C8 C -0.0868(5) -0.0188(6) 0.4565(3) 0.0415(13) Uani 1 d . . H8A H -0.0984(5) -0.0544(6) 0.5125(3) 0.050 Uiso 1 calc R . C9 C 0.0047(4) 0.0924(6) 0.4487(3) 0.0336(11) Uani 1 d . . H9A H 0.0543(4) 0.1319(6) 0.4992(3) 0.040 Uiso 1 calc R . C10 C 0.0237(4) 0.1466(5) 0.3643(3) 0.0256(10) Uani 1 d . . C11 C 0.0216(5) 0.6033(6) 0.2765(3) 0.0467(14) Uani 1 d . . H11A H -0.0376(5) 0.5202(6) 0.2677(3) 0.070 Uiso 1 calc R . H11B H -0.0247(5) 0.6850(6) 0.2476(3) 0.070 Uiso 1 calc R . H11C H 0.0416(5) 0.6225(6) 0.3390(3) 0.070 Uiso 1 calc R . C12 C 0.2545(5) 0.7050(6) 0.2499(3) 0.0434(13) Uani 1 d . . H12A H 0.3391(5) 0.6847(6) 0.2247(3) 0.065 Uiso 1 calc R . H12B H 0.2759(5) 0.7249(6) 0.3122(3) 0.065 Uiso 1 calc R . H12C H 0.2095(5) 0.7873(6) 0.2208(3) 0.065 Uiso 1 calc R . C13 C 0.6055(4) 0.3108(7) 0.1952(3) 0.0442(12) Uani 1 d . . H13A H 0.6294(4) 0.4075(7) 0.1802(3) 0.066 Uiso 1 calc R . H13B H 0.5581(4) 0.2643(7) 0.1437(3) 0.066 Uiso 1 calc R . H13C H 0.6889(4) 0.2583(7) 0.2153(3) 0.066 Uiso 1 calc R . C14 C 0.4415(5) 0.1288(6) 0.3150(3) 0.0423(13) Uani 1 d . . H14A H 0.3816(5) 0.1325(6) 0.3613(3) 0.063 Uiso 1 calc R . H14B H 0.5245(5) 0.0758(6) 0.3354(3) 0.063 Uiso 1 calc R . H14C H 0.3936(5) 0.0818(6) 0.2638(3) 0.063 Uiso 1 calc R . C15 C 0.5790(5) 0.4073(6) 0.3879(3) 0.0380(12) Uani 1 d . . C16 C 0.4949(6) 0.3971(9) 0.4675(3) 0.070(2) Uani 1 d . . H16A H 0.4749(6) 0.2979(9) 0.4786(3) 0.105 Uiso 1 calc R . H16B H 0.4091(6) 0.4494(9) 0.4548(3) 0.105 Uiso 1 calc R . H16C H 0.5482(6) 0.4377(9) 0.5190(3) 0.105 Uiso 1 calc R . C17 C 0.7178(5) 0.3295(8) 0.4121(4) 0.069(2) Uani 1 d . . H17A H 0.7005(5) 0.2297(8) 0.4233(4) 0.103 Uiso 1 calc R . H17B H 0.7666(5) 0.3725(8) 0.4643(4) 0.103 Uiso 1 calc R . H17C H 0.7734(5) 0.3373(8) 0.3637(4) 0.103 Uiso 1 calc R . C18 C 0.6104(6) 0.5646(7) 0.3706(4) 0.062(2) Uani 1 d . . H18A H 0.5246(6) 0.6158(7) 0.3552(4) 0.094 Uiso 1 calc R . H18B H 0.6667(6) 0.5711(7) 0.3224(4) 0.094 Uiso 1 calc R . H18C H 0.6599(6) 0.6062(7) 0.4231(4) 0.094 Uiso 1 calc R . C19 C -0.0106(4) 0.3451(5) 0.0640(3) 0.0321(11) Uani 1 d . . C20 C -0.0243(4) 0.3091(6) -0.0330(2) 0.0366(11) Uani 1 d . . H20A H 0.0529(4) 0.2501(6) -0.0451(2) 0.055 Uiso 1 calc R . H20B H -0.0248(4) 0.3964(6) -0.0670(2) 0.055 Uiso 1 calc R . H20C H -0.1099(4) 0.2578(6) -0.0489(2) 0.055 Uiso 1 calc R . C21 C 0.2112(4) 0.1989(5) 0.0901(3) 0.0256(10) Uani 1 d . . C22 C 0.2843(4) 0.2580(6) 0.0170(3) 0.0280(11) Uani 1 d . . C23 C 0.3391(5) 0.1620(6) -0.0396(3) 0.0386(13) Uani 1 d . . H23A H 0.3223(5) 0.0638(6) -0.0349(3) 0.046 Uiso 1 calc R . C24 C 0.4194(6) 0.2125(7) -0.1036(3) 0.052(2) Uani 1 d . . H24A H 0.4576(6) 0.1483(7) -0.1413(3) 0.062 Uiso 1 calc R . C25 C 0.4417(6) 0.3575(7) -0.1106(3) 0.050(2) Uani 1 d . . H25A H 0.4957(6) 0.3912(7) -0.1533(3) 0.060 Uiso 1 calc R . C26 C 0.3860(5) 0.4543(6) -0.0559(3) 0.0431(14) Uani 1 d . . H26A H 0.4009(5) 0.5525(6) -0.0620(3) 0.052 Uiso 1 calc R . C27 C 0.3075(5) 0.4043(6) 0.0083(3) 0.0321(11) Uani 1 d . . H27A H 0.2701(5) 0.4691(6) 0.0459(3) 0.039 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 Si1 0.0238(6) 0.0257(6) 0.0305(6) -0.0031(7) 0.0031(5) 0.0015(7) O1 0.035(2) 0.042(2) 0.031(2) -0.008(2) 0.0040(14) -0.011(2) O2 0.0206(14) 0.027(2) 0.0292(14) 0.0018(14) 0.0049(12) 0.0021(15) O3 0.038(2) 0.049(2) 0.045(2) -0.005(2) -0.001(2) 0.015(2) O4 0.037(2) 0.029(2) 0.031(2) 0.004(2) 0.0096(14) 0.003(2) N1 0.024(2) 0.029(2) 0.024(2) 0.000(2) 0.0060(14) 0.003(2) N2 0.029(2) 0.028(2) 0.018(2) 0.002(2) 0.0058(14) -0.002(2) N3 0.025(2) 0.027(2) 0.023(2) 0.002(2) 0.0060(14) 0.001(2) C1 0.027(2) 0.025(3) 0.025(2) -0.005(2) 0.006(2) -0.002(2) C2 0.022(2) 0.030(2) 0.023(2) -0.006(2) 0.003(2) 0.006(2) C3 0.035(2) 0.022(2) 0.030(2) -0.002(2) 0.009(2) 0.004(2) C4 0.025(2) 0.027(3) 0.034(3) -0.003(2) 0.005(2) -0.001(2) C5 0.025(2) 0.027(2) 0.033(2) -0.002(2) 0.009(2) -0.001(2) C6 0.032(2) 0.029(3) 0.041(3) -0.004(2) 0.009(2) -0.004(2) C7 0.043(3) 0.027(3) 0.054(3) 0.009(3) 0.017(2) -0.007(3) C8 0.051(3) 0.038(3) 0.040(3) 0.013(3) 0.020(2) 0.006(3) C9 0.035(2) 0.035(3) 0.032(2) 0.005(2) 0.008(2) 0.003(3) C10 0.021(2) 0.027(2) 0.030(2) 0.000(2) 0.010(2) 0.001(2) C11 0.042(3) 0.042(3) 0.059(3) -0.002(3) 0.017(2) 0.012(3) C12 0.053(3) 0.026(3) 0.051(3) 0.004(2) 0.004(2) 0.002(3) C13 0.035(2) 0.055(3) 0.044(2) 0.001(3) 0.009(2) 0.019(3) C14 0.047(3) 0.029(3) 0.049(3) 0.006(3) -0.003(2) 0.000(3) C15 0.030(2) 0.038(3) 0.045(3) -0.012(3) 0.000(2) 0.001(3) C16 0.066(4) 0.108(6) 0.034(3) -0.019(4) -0.004(3) -0.016(4) C17 0.054(3) 0.062(4) 0.081(4) -0.029(4) -0.029(3) 0.014(4) C18 0.064(4) 0.043(4) 0.076(4) -0.018(3) -0.015(3) -0.011(3) C19 0.031(2) 0.033(3) 0.031(2) 0.000(2) 0.002(2) 0.000(2) C20 0.034(2) 0.041(3) 0.032(2) 0.003(3) -0.008(2) 0.005(3) C21 0.026(2) 0.025(3) 0.025(2) -0.002(2) 0.000(2) -0.002(2) C22 0.022(2) 0.038(3) 0.024(2) -0.002(2) 0.004(2) -0.001(2) C23 0.039(3) 0.042(3) 0.038(3) -0.001(2) 0.015(2) -0.007(3) C24 0.056(4) 0.056(4) 0.048(3) -0.008(3) 0.027(3) -0.009(3) C25 0.051(3) 0.068(5) 0.036(3) 0.012(3) 0.020(2) -0.008(3) C26 0.039(3) 0.044(3) 0.046(3) 0.013(3) 0.005(2) -0.010(3) C27 0.033(2) 0.031(3) 0.033(3) 0.005(2) 0.007(2) 0.001(2) _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 Si1 O2 1.669(3) . ? Si1 C13 1.858(4) . ? Si1 C14 1.862(5) . ? Si1 C15 1.898(5) . ? O1 C4 1.207(5) . ? O2 C1 1.429(5) . ? O3 C19 1.201(5) . ? O4 C21 1.207(5) . ? N1 C2 1.290(5) . ? N1 C10 1.389(6) . ? N2 N3 1.403(4) . ? N2 C21 1.425(5) . ? N2 C19 1.435(5) . ? N3 C2 1.386(5) . ? N3 C4 1.415(6) . ? C1 C2 1.518(6) . ? C1 C3 1.531(6) . ? C3 C11 1.523(6) . ? C3 C12 1.524(7) . ? C4 C5 1.464(6) . ? C5 C10 1.394(6) . ? C5 C6 1.397(6) . ? C6 C7 1.377(6) . ? C7 C8 1.389(7) . ? C8 C9 1.372(7) . ? C9 C10 1.405(5) . ? C15 C18 1.520(8) . ? C15 C17 1.528(7) . ? C15 C16 1.534(7) . ? C19 C20 1.497(5) . ? C21 C22 1.486(6) . ? C22 C27 1.385(7) . ? C22 C23 1.384(6) . ? C23 C24 1.391(6) . ? C24 C25 1.370(8) . ? C25 C26 1.374(7) . ? C26 C27 1.381(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 O2 Si1 C13 102.9(2) . . ? O2 Si1 C14 111.3(2) . . ? C13 Si1 C14 110.3(3) . . ? O2 Si1 C15 112.9(2) . . ? C13 Si1 C15 110.9(2) . . ? C14 Si1 C15 108.6(2) . . ? C1 O2 Si1 125.9(2) . . ? C2 N1 C10 118.7(4) . . ? N3 N2 C21 112.8(3) . . ? N3 N2 C19 112.2(3) . . ? C21 N2 C19 124.1(3) . . ? C2 N3 N2 121.8(3) . . ? C2 N3 C4 123.9(3) . . ? N2 N3 C4 114.2(3) . . ? O2 C1 C2 111.1(3) . . ? O2 C1 C3 110.8(3) . . ? C2 C1 C3 114.8(3) . . ? N1 C2 N3 122.1(4) . . ? N1 C2 C1 116.9(4) . . ? N3 C2 C1 120.9(3) . . ? C11 C3 C12 111.1(4) . . ? C11 C3 C1 110.1(4) . . ? C12 C3 C1 110.8(3) . . ? O1 C4 N3 120.4(4) . . ? O1 C4 C5 126.5(4) . . ? N3 C4 C5 113.1(4) . . ? C10 C5 C6 121.1(4) . . ? C10 C5 C4 119.0(4) . . ? C6 C5 C4 119.9(4) . . ? C7 C6 C5 119.2(4) . . ? C6 C7 C8 120.2(4) . . ? C9 C8 C7 120.9(4) . . ? C8 C9 C10 120.1(5) . . ? N1 C10 C5 123.0(4) . . ? N1 C10 C9 118.5(4) . . ? C5 C10 C9 118.5(4) . . ? C18 C15 C17 108.0(5) . . ? C18 C15 C16 109.2(5) . . ? C17 C15 C16 108.1(5) . . ? C18 C15 Si1 111.8(4) . . ? C17 C15 Si1 106.7(3) . . ? C16 C15 Si1 112.8(3) . . ? O3 C19 N2 118.2(4) . . ? O3 C19 C20 123.4(4) . . ? N2 C19 C20 118.4(4) . . ? O4 C21 N2 121.0(4) . . ? O4 C21 C22 122.9(4) . . ? N2 C21 C22 115.9(4) . . ? C27 C22 C23 119.7(5) . . ? C27 C22 C21 121.9(4) . . ? C23 C22 C21 118.2(4) . . ? C22 C23 C24 119.9(5) . . ? C25 C24 C23 119.4(6) . . ? C24 C25 C26 121.3(5) . . ? C25 C26 C27 119.4(5) . . ? C26 C27 C22 120.3(5) . . ? _refine_diff_density_max 0.206 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.047 data_17 _database_code_CSD 167262 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C23 H29 N3 O3 Si' _chemical_formula_weight 423.58 _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' 'Si' 'Si' 0.0817 0.0704 '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 8.889(2) _cell_length_b 11.391(2) _cell_length_c 23.399(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2369.1(8) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 38 _cell_measurement_theta_min 5.37 _cell_measurement_theta_max 12.57 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.64 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.188 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.126 _exptl_absorpt_correction_type 'not applied' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'Siemens P4 diffractometer' _diffrn_measurement_method 'omega scan' _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 2759 _diffrn_reflns_av_R_equivalents 0.0148 _diffrn_reflns_av_sigmaI/netI 0.0509 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2687 _reflns_number_observed 1899 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'XSCANS (Fait, 1991)' _computing_cell_refinement 'XSCANS (Fait, 1991)' _computing_data_reduction 'XSCANS (Fait, 1991)' _computing_structure_solution 'SHELXTL/PC ver5.0 (Sheldrick, 1996)' _computing_structure_refinement 'SHELXTL/PC ver5.0 (Sheldrick, 1996)' _computing_molecular_graphics 'SHELXTL/PC ver5.0 (Sheldrick, 1996)' _computing_publication_material 'SHELXTL/PC ver5.0 (Sheldrick, 1996)' _refine_special_details ; Refinement on F^2^ for ALL reflections. 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^)+(0.0667P)^2^+1.4067P] 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 'riding model' _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 0.05(33) _refine_ls_number_reflns 2687 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0867 _refine_ls_R_factor_obs 0.0537 _refine_ls_wR_factor_all 0.1387 _refine_ls_wR_factor_obs 0.1186 _refine_ls_goodness_of_fit_all 0.955 _refine_ls_goodness_of_fit_obs 0.991 _refine_ls_restrained_S_all 0.955 _refine_ls_restrained_S_obs 0.991 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Si1 Si 0.1514(2) 0.54287(15) 0.82774(6) 0.0521(4) Uani 1 d . . O1 O -0.0040(4) 0.7163(3) 1.08654(15) 0.0519(10) Uani 1 d . . O2 O 0.1466(4) 0.5167(3) 0.89730(12) 0.0435(8) Uani 1 d . . O3 O 0.3213(4) 0.7910(3) 1.03530(15) 0.0450(9) Uani 1 d . . N1 N 0.2057(4) 0.4254(3) 1.0232(2) 0.0366(9) Uani 1 d . . N2 N 0.1229(4) 0.7241(3) 0.9849(2) 0.0353(9) Uani 1 d . . H2A H 0.0633(4) 0.7327(3) 0.9563(2) 0.042 Uiso 1 calc R . N3 N 0.1273(4) 0.6209(3) 1.0166(2) 0.0335(9) Uani 1 d . . C1 C 0.2706(5) 0.5340(4) 0.9366(2) 0.0348(10) Uani 1 d . . H1B H 0.3111(5) 0.6134(4) 0.9318(2) 0.042 Uiso 1 calc R . C2 C 0.1995(5) 0.5227(4) 0.9954(2) 0.0347(11) Uani 1 d . . C3 C 0.2190(5) 0.8116(4) 1.0021(2) 0.0359(11) Uani 1 d . . C4 C 0.0565(5) 0.6261(4) 1.0706(2) 0.0390(12) Uani 1 d . . C5 C 0.0604(5) 0.5151(4) 1.1007(2) 0.0389(12) Uani 1 d . . C6 C -0.0103(6) 0.5031(5) 1.1536(2) 0.0505(14) Uani 1 d . . H6A H -0.0603(6) 0.5668(5) 1.1696(2) 0.061 Uiso 1 calc R . C7 C -0.0066(7) 0.3974(5) 1.1825(2) 0.060(2) Uani 1 d . . H7A H -0.0539(7) 0.3893(5) 1.2177(2) 0.072 Uiso 1 calc R . C8 C 0.0688(7) 0.3037(5) 1.1580(2) 0.059(2) Uani 1 d . . H8A H 0.0721(7) 0.2324(5) 1.1774(2) 0.070 Uiso 1 calc R . C9 C 0.1387(6) 0.3131(4) 1.1061(2) 0.0494(13) Uani 1 d . . H9A H 0.1880(6) 0.2486(4) 1.0905(2) 0.059 Uiso 1 calc R . C10 C 0.1360(5) 0.4195(4) 1.0766(2) 0.0368(11) Uani 1 d . . C11 C 0.3946(5) 0.4452(5) 0.9274(2) 0.0464(12) Uani 1 d . . H11A H 0.4365(5) 0.4551(5) 0.8899(2) 0.070 Uiso 1 calc R . H11B H 0.3543(5) 0.3673(5) 0.9310(2) 0.070 Uiso 1 calc R . H11C H 0.4719(5) 0.4567(5) 0.9556(2) 0.070 Uiso 1 calc R . C12 C 0.2503(9) 0.6828(6) 0.8135(3) 0.086(2) Uani 1 d . . H12A H 0.3519(9) 0.6775(6) 0.8271(3) 0.129 Uiso 1 calc R . H12B H 0.1994(9) 0.7456(6) 0.8329(3) 0.129 Uiso 1 calc R . H12C H 0.2508(9) 0.6979(6) 0.7731(3) 0.129 Uiso 1 calc R . C13 C 0.2535(9) 0.4213(7) 0.7897(3) 0.101(3) Uani 1 d . . H13A H 0.2032(9) 0.3481(7) 0.7968(3) 0.152 Uiso 1 calc R . H13B H 0.3550(9) 0.4168(7) 0.8036(3) 0.152 Uiso 1 calc R . H13C H 0.2544(9) 0.4368(7) 0.7494(3) 0.152 Uiso 1 calc R . C14 C -0.0470(7) 0.5427(8) 0.8032(3) 0.081(2) Uani 1 d . . C15 C -0.1266(9) 0.6549(10) 0.8270(3) 0.132(4) Uani 1 d . . H15A H -0.0750(9) 0.7236(10) 0.8136(3) 0.199 Uiso 1 calc R . H15B H -0.1246(9) 0.6533(10) 0.8680(3) 0.199 Uiso 1 calc R . H15C H -0.2291(9) 0.6566(10) 0.8141(3) 0.199 Uiso 1 calc R . C16 C -0.0543(8) 0.5461(8) 0.7373(2) 0.099(3) Uani 1 d . . H16A H -0.0058(8) 0.6160(8) 0.7237(2) 0.149 Uiso 1 calc R . H16B H -0.1576(8) 0.5459(8) 0.7253(2) 0.149 Uiso 1 calc R . H16C H -0.0041(8) 0.4784(8) 0.7220(2) 0.149 Uiso 1 calc R . C17 C -0.1248(11) 0.4309(11) 0.8233(3) 0.178(6) Uani 1 d . . H17A H -0.1216(11) 0.4271(11) 0.8643(3) 0.267 Uiso 1 calc R . H17B H -0.0743(11) 0.3639(11) 0.8075(3) 0.267 Uiso 1 calc R . H17C H -0.2277(11) 0.4314(11) 0.8108(3) 0.267 Uiso 1 calc R . C18 C 0.1914(5) 0.9305(4) 0.9769(2) 0.0379(11) Uani 1 d . . C19 C 0.2783(5) 1.0224(4) 0.9974(2) 0.0444(12) Uani 1 d . . H19A H 0.3521(5) 1.0085(4) 1.0247(2) 0.053 Uiso 1 calc R . C20 C 0.2549(6) 1.1351(4) 0.9769(3) 0.0522(15) Uani 1 d . . H20A H 0.3132(6) 1.1967(4) 0.9907(3) 0.063 Uiso 1 calc R . C21 C 0.1472(7) 1.1568(5) 0.9369(3) 0.0565(15) Uani 1 d . . H21A H 0.1325(7) 1.2329(5) 0.9236(3) 0.068 Uiso 1 calc R . C22 C 0.0597(6) 1.0662(5) 0.9157(2) 0.0506(14) Uani 1 d . . H22A H -0.0139(6) 1.0815(5) 0.8884(2) 0.061 Uiso 1 calc R . C23 C 0.0821(6) 0.9523(5) 0.9352(2) 0.0445(12) Uani 1 d . . H23A H 0.0247(6) 0.8909(5) 0.9207(2) 0.053 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 Si1 0.0559(9) 0.0586(9) 0.0417(8) 0.0041(8) -0.0039(7) -0.0100(9) O1 0.056(2) 0.045(2) 0.055(2) -0.002(2) 0.009(2) 0.016(2) O2 0.043(2) 0.048(2) 0.040(2) 0.001(2) -0.004(2) -0.005(2) O3 0.032(2) 0.046(2) 0.058(2) 0.000(2) -0.005(2) 0.003(2) N1 0.038(2) 0.027(2) 0.045(2) -0.001(2) -0.002(2) -0.001(2) N2 0.036(2) 0.029(2) 0.041(2) 0.002(2) -0.003(2) 0.001(2) N3 0.037(2) 0.026(2) 0.037(2) 0.002(2) 0.003(2) 0.001(2) C1 0.036(2) 0.031(2) 0.037(2) -0.004(2) -0.001(2) -0.005(2) C2 0.032(2) 0.031(2) 0.042(3) -0.001(2) -0.002(2) -0.005(2) C3 0.029(2) 0.035(3) 0.043(3) -0.004(2) 0.009(2) 0.005(2) C4 0.033(3) 0.041(3) 0.043(3) 0.000(2) -0.003(2) 0.003(2) C5 0.035(2) 0.046(3) 0.036(3) 0.004(2) -0.002(2) -0.002(2) C6 0.048(3) 0.056(3) 0.047(3) -0.001(3) 0.005(3) 0.005(3) C7 0.060(4) 0.073(4) 0.046(3) 0.011(3) 0.004(3) 0.000(3) C8 0.066(4) 0.053(3) 0.057(4) 0.017(3) -0.008(3) -0.011(3) C9 0.059(3) 0.038(3) 0.051(3) 0.009(2) 0.001(3) 0.000(3) C10 0.033(2) 0.037(3) 0.040(3) 0.002(2) -0.005(2) -0.007(2) C11 0.043(3) 0.052(3) 0.044(3) -0.003(3) 0.005(2) 0.000(3) C12 0.115(6) 0.091(5) 0.053(4) 0.015(4) -0.005(4) -0.044(5) C13 0.124(7) 0.124(6) 0.056(4) -0.013(4) 0.007(4) 0.043(6) C14 0.067(4) 0.128(6) 0.047(3) 0.012(4) -0.009(3) -0.011(5) C15 0.078(5) 0.241(12) 0.078(5) -0.012(7) -0.003(5) 0.067(7) C16 0.088(5) 0.161(7) 0.049(4) 0.002(5) -0.019(3) -0.012(6) C17 0.156(9) 0.302(15) 0.076(5) 0.036(8) -0.041(6) -0.173(10) C18 0.031(2) 0.034(2) 0.049(3) -0.004(2) 0.013(2) 0.003(2) C19 0.036(2) 0.036(3) 0.062(3) -0.008(3) 0.006(3) -0.006(2) C20 0.050(3) 0.037(3) 0.070(4) -0.007(3) 0.019(3) -0.009(3) C21 0.066(4) 0.037(3) 0.067(4) 0.006(3) 0.019(4) 0.000(3) C22 0.055(3) 0.043(3) 0.053(3) 0.008(3) 0.002(3) 0.005(3) C23 0.048(3) 0.040(3) 0.046(3) -0.003(3) 0.008(3) -0.005(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 Si1 O2 1.655(3) . ? Si1 C12 1.850(7) . ? Si1 C14 1.854(6) . ? Si1 C13 1.880(7) . ? O1 C4 1.218(5) . ? O2 C1 1.448(5) . ? O3 C3 1.219(5) . ? N1 C2 1.287(6) . ? N1 C10 1.396(6) . ? N2 C3 1.372(6) . ? N2 N3 1.390(5) . ? N3 C2 1.381(5) . ? N3 C4 1.414(6) . ? C1 C11 1.512(6) . ? C1 C2 1.520(6) . ? C3 C18 1.498(7) . ? C4 C5 1.447(6) . ? C5 C6 1.394(7) . ? C5 C10 1.399(6) . ? C6 C7 1.381(7) . ? C7 C8 1.385(8) . ? C8 C9 1.368(7) . ? C9 C10 1.394(7) . ? C14 C17 1.524(11) . ? C14 C16 1.542(8) . ? C14 C15 1.563(11) . ? C18 C19 1.387(6) . ? C18 C23 1.398(7) . ? C19 C20 1.386(7) . ? C20 C21 1.362(8) . ? C21 C22 1.384(7) . ? C22 C23 1.390(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 O2 Si1 C12 110.1(2) . . ? O2 Si1 C14 106.3(2) . . ? C12 Si1 C14 113.4(4) . . ? O2 Si1 C13 110.2(3) . . ? C12 Si1 C13 108.7(4) . . ? C14 Si1 C13 108.2(4) . . ? C1 O2 Si1 125.5(3) . . ? C2 N1 C10 118.4(4) . . ? C3 N2 N3 116.2(4) . . ? C2 N3 N2 120.5(3) . . ? C2 N3 C4 124.1(4) . . ? N2 N3 C4 115.4(3) . . ? O2 C1 C11 112.0(4) . . ? O2 C1 C2 104.3(3) . . ? C11 C1 C2 112.0(4) . . ? N1 C2 N3 122.4(4) . . ? N1 C2 C1 120.8(4) . . ? N3 C2 C1 116.7(4) . . ? O3 C3 N2 120.7(4) . . ? O3 C3 C18 123.2(4) . . ? N2 C3 C18 116.1(4) . . ? O1 C4 N3 120.3(4) . . ? O1 C4 C5 126.8(4) . . ? N3 C4 C5 112.9(4) . . ? C6 C5 C10 119.8(5) . . ? C6 C5 C4 120.5(5) . . ? C10 C5 C4 119.7(4) . . ? C7 C6 C5 120.6(5) . . ? C6 C7 C8 118.8(5) . . ? C9 C8 C7 121.7(5) . . ? C8 C9 C10 120.0(5) . . ? C9 C10 N1 118.5(4) . . ? C9 C10 C5 119.1(5) . . ? N1 C10 C5 122.4(4) . . ? C17 C14 C16 108.1(7) . . ? C17 C14 C15 111.5(7) . . ? C16 C14 C15 108.5(6) . . ? C17 C14 Si1 109.7(6) . . ? C16 C14 Si1 110.5(5) . . ? C15 C14 Si1 108.6(5) . . ? C19 C18 C23 119.6(5) . . ? C19 C18 C3 117.1(4) . . ? C23 C18 C3 123.3(4) . . ? C20 C19 C18 119.7(5) . . ? C21 C20 C19 120.7(5) . . ? C20 C21 C22 120.4(5) . . ? C21 C22 C23 119.8(5) . . ? C22 C23 C18 119.6(5) . . ? _refine_diff_density_max 0.198 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.044 data_19a _database_code_CSD 167263 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H25 N3 O5' _chemical_formula_weight 483.51 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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.167(2) _cell_length_b 25.688(3) _cell_length_c 10.311(2) _cell_angle_alpha 90.00 _cell_angle_beta 115.860(10) _cell_angle_gamma 90.00 _cell_volume 2423.3(7) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 41 _cell_measurement_theta_min 5.37 _cell_measurement_theta_max 12.76 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.57 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type 'not applied' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'Siemens P4 diffractometer' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 1000 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 11 _diffrn_reflns_number 5740 _diffrn_reflns_av_R_equivalents 0.0498 _diffrn_reflns_av_sigmaI/netI 0.0923 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4685 _reflns_number_gt 2032 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XSCANS (Fait, 1991)' _computing_cell_refinement 'XSCANS (Fait, 1991)' _computing_data_reduction 'XSCANS (Fait, 1991)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1000P)^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_number_reflns 4685 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2507 _refine_ls_R_factor_gt 0.1069 _refine_ls_wR_factor_ref 0.3598 _refine_ls_wR_factor_gt 0.2588 _refine_ls_goodness_of_fit_ref 1.760 _refine_ls_restrained_S_all 1.760 _refine_ls_shift/su_max 0.000 _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 0.2494(5) 0.2080(2) 0.5569(5) 0.0531(15) Uani 1 1 d . . . O2 O 0.3187(6) 0.1713(2) 0.9553(5) 0.0648(17) Uani 1 1 d . . . O3 O 0.2575(5) 0.0835(2) 0.6034(5) 0.0480(13) Uani 1 1 d . . . O4 O 0.0641(5) 0.05334(19) 0.6981(5) 0.0478(13) Uani 1 1 d . . . O5 O -0.0346(5) 0.1272(2) 0.5817(5) 0.0547(15) Uani 1 1 d . . . N1 N 0.6328(6) 0.1370(2) 0.6241(5) 0.0351(13) Uani 1 1 d . . . N2 N 0.3739(6) 0.1445(2) 0.7745(5) 0.0382(14) Uani 1 1 d . . . N3 N 0.4449(5) 0.1557(2) 0.6908(5) 0.0333(13) Uani 1 1 d . . . C1 C 0.6397(7) 0.0921(2) 0.8343(6) 0.0350(16) Uani 1 1 d . . . H1B H 0.5648 0.0852 0.8678 0.042 Uiso 1 1 calc R . . C2 C 0.5717(6) 0.1300(2) 0.7071(6) 0.0308(15) Uani 1 1 d . . . C4 C 0.3650(7) 0.1903(3) 0.5700(6) 0.0371(16) Uani 1 1 d . . . C5 C 0.4368(7) 0.1967(3) 0.4779(6) 0.0360(16) Uani 1 1 d . . . C6 C 0.3750(8) 0.2308(3) 0.3577(6) 0.0430(18) Uani 1 1 d . . . H6A H 0.2866 0.2473 0.3366 0.052 Uiso 1 1 calc R . . C7 C 0.4449(9) 0.2393(3) 0.2740(7) 0.051(2) Uani 1 1 d . . . H7A H 0.4030 0.2610 0.1941 0.061 Uiso 1 1 calc R . . C8 C 0.5790(8) 0.2158(3) 0.3066(7) 0.048(2) Uani 1 1 d . . . H8A H 0.6270 0.2225 0.2496 0.058 Uiso 1 1 calc R . . C9 C 0.6417(8) 0.1824(3) 0.4235(7) 0.0432(18) Uani 1 1 d . . . H9A H 0.7308 0.1665 0.4443 0.052 Uiso 1 1 calc R . . C10 C 0.5701(7) 0.1729(3) 0.5091(6) 0.0365(17) Uani 1 1 d . . . C11 C 0.7690(7) 0.1187(3) 0.9610(6) 0.0358(16) Uani 1 1 d . . . C12 C 0.7700(8) 0.1183(3) 1.0959(7) 0.050(2) Uani 1 1 d . . . H12A H 0.6926 0.1035 1.1079 0.060 Uiso 1 1 calc R . . C13 C 0.8876(9) 0.1401(3) 1.2140(7) 0.055(2) Uani 1 1 d . . . H13A H 0.8873 0.1408 1.3040 0.066 Uiso 1 1 calc R . . C14 C 1.0016(9) 0.1602(3) 1.1967(7) 0.055(2) Uani 1 1 d . . . H14A H 1.0818 0.1729 1.2766 0.066 Uiso 1 1 calc R . . C15 C 1.0016(8) 0.1622(3) 1.0627(8) 0.053(2) Uani 1 1 d . . . H15A H 1.0792 0.1774 1.0517 0.063 Uiso 1 1 calc R . . C16 C 0.8829(8) 0.1411(3) 0.9437(7) 0.0446(18) Uani 1 1 d . . . H16A H 0.8813 0.1423 0.8529 0.053 Uiso 1 1 calc R . . C17 C 0.6765(7) 0.0397(3) 0.7880(6) 0.0387(17) Uani 1 1 d . . . C18 C 0.8198(8) 0.0229(3) 0.8299(7) 0.049(2) Uani 1 1 d . . . H18A H 0.8978 0.0448 0.8830 0.058 Uiso 1 1 calc R . . C19 C 0.8458(9) -0.0271(3) 0.7916(7) 0.057(2) Uani 1 1 d . . . H19A H 0.9413 -0.0389 0.8234 0.068 Uiso 1 1 calc R . . C20 C 0.7325(9) -0.0586(3) 0.7081(7) 0.056(2) Uani 1 1 d . . . H20A H 0.7510 -0.0911 0.6797 0.067 Uiso 1 1 calc R . . C21 C 0.5901(10) -0.0424(3) 0.6657(8) 0.065(3) Uani 1 1 d . . . H21A H 0.5125 -0.0643 0.6123 0.079 Uiso 1 1 calc R . . C22 C 0.5641(8) 0.0073(3) 0.7037(7) 0.054(2) Uani 1 1 d . . . H22A H 0.4682 0.0188 0.6711 0.065 Uiso 1 1 calc R . . C23 C 0.4746(9) 0.2255(3) 0.9045(7) 0.052(2) Uani 1 1 d . . . H23A H 0.4727 0.2466 0.9805 0.077 Uiso 1 1 calc R . . H23B H 0.4382 0.2453 0.8168 0.077 Uiso 1 1 calc R . . H23C H 0.5732 0.2148 0.9295 0.077 Uiso 1 1 calc R . . C24 C 0.3833(8) 0.1798(3) 0.8844(7) 0.0389(17) Uani 1 1 d . . . C25 C 0.2666(7) 0.1032(3) 0.7125(6) 0.0362(17) Uani 1 1 d . . . C26 C 0.1853(7) 0.0842(3) 0.7957(7) 0.0442(18) Uani 1 1 d . . . H26A H 0.1514 0.1134 0.8343 0.053 Uiso 1 1 calc R . . C27 C 0.2813(9) 0.0473(4) 0.9158(8) 0.073(3) Uani 1 1 d . . . H27A H 0.2283 0.0355 0.9678 0.110 Uiso 1 1 calc R . . H27B H 0.3680 0.0653 0.9804 0.110 Uiso 1 1 calc R . . H27C H 0.3079 0.0179 0.8747 0.110 Uiso 1 1 calc R . . C28 C -0.0427(7) 0.0813(3) 0.5916(7) 0.0462(19) Uani 1 1 d . . . C29 C -0.1609(8) 0.0466(3) 0.4906(8) 0.060(2) Uani 1 1 d . . . H29A H -0.2340 0.0672 0.4165 0.090 Uiso 1 1 calc R . . H29B H -0.2045 0.0280 0.5428 0.090 Uiso 1 1 calc R . . H29C H -0.1200 0.0222 0.4476 0.090 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.031(3) 0.075(4) 0.039(3) 0.019(3) 0.002(2) 0.009(3) O2 0.077(4) 0.080(4) 0.046(3) -0.026(3) 0.033(3) -0.027(3) O3 0.046(3) 0.053(3) 0.037(3) -0.012(2) 0.010(2) -0.013(2) O4 0.043(3) 0.045(3) 0.040(3) 0.001(2) 0.004(2) -0.006(2) O5 0.043(3) 0.047(3) 0.053(3) 0.002(3) 0.002(2) 0.000(3) N1 0.033(3) 0.039(3) 0.026(3) 0.004(2) 0.006(2) 0.006(3) N2 0.037(3) 0.044(3) 0.021(2) 0.002(2) 0.002(2) 0.006(3) N3 0.028(3) 0.041(3) 0.022(2) 0.000(2) 0.003(2) 0.003(3) C1 0.037(4) 0.036(4) 0.021(3) 0.002(3) 0.002(3) 0.003(3) C2 0.019(3) 0.037(4) 0.028(3) -0.005(3) 0.003(3) 0.001(3) C4 0.029(4) 0.041(4) 0.025(3) -0.001(3) -0.003(3) 0.005(3) C5 0.031(4) 0.040(4) 0.024(3) -0.004(3) 0.001(3) 0.001(3) C6 0.049(4) 0.041(4) 0.027(3) 0.002(3) 0.005(3) 0.010(4) C7 0.062(5) 0.049(5) 0.026(3) 0.004(3) 0.004(4) 0.001(4) C8 0.048(5) 0.068(5) 0.029(3) 0.005(3) 0.017(3) 0.008(4) C9 0.044(4) 0.048(4) 0.031(3) 0.002(3) 0.010(3) 0.001(4) C10 0.035(4) 0.041(4) 0.022(3) -0.002(3) 0.002(3) -0.006(3) C11 0.033(4) 0.039(4) 0.027(3) 0.004(3) 0.005(3) 0.007(3) C12 0.058(5) 0.052(5) 0.029(3) 0.004(3) 0.008(3) 0.001(4) C13 0.052(5) 0.075(6) 0.024(3) 0.000(4) 0.003(3) 0.007(5) C14 0.048(5) 0.052(5) 0.036(4) -0.007(4) -0.008(3) 0.016(4) C15 0.040(4) 0.039(4) 0.054(5) 0.003(4) -0.003(4) 0.003(4) C16 0.043(4) 0.049(4) 0.030(3) 0.002(3) 0.004(3) 0.003(4) C17 0.039(4) 0.037(4) 0.026(3) 0.001(3) 0.001(3) 0.003(3) C18 0.053(5) 0.048(5) 0.033(3) -0.006(3) 0.008(3) 0.009(4) C19 0.061(5) 0.053(5) 0.039(4) 0.003(4) 0.006(4) 0.012(4) C20 0.072(6) 0.038(4) 0.038(4) -0.007(3) 0.005(4) 0.008(4) C21 0.056(5) 0.043(5) 0.060(5) -0.007(4) -0.010(4) -0.003(4) C22 0.044(4) 0.045(5) 0.046(4) -0.001(4) -0.007(3) 0.011(4) C23 0.061(5) 0.040(4) 0.039(4) -0.007(3) 0.008(4) -0.002(4) C24 0.037(4) 0.044(4) 0.026(3) -0.006(3) 0.005(3) 0.004(3) C25 0.030(4) 0.040(4) 0.026(3) -0.001(3) 0.000(3) 0.005(3) C26 0.039(4) 0.052(5) 0.032(3) 0.004(3) 0.007(3) -0.002(4) C27 0.067(6) 0.083(7) 0.044(4) 0.031(4) 0.000(4) -0.012(5) C28 0.029(4) 0.066(6) 0.040(4) -0.005(4) 0.011(3) 0.004(4) C29 0.049(5) 0.067(6) 0.045(4) -0.009(4) 0.003(4) 0.001(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 O1 C4 1.212(8) . ? O2 C24 1.196(8) . ? O3 C25 1.200(7) . ? O4 C28 1.364(8) . ? O4 C26 1.442(8) . ? O5 C28 1.189(9) . ? N1 C2 1.271(8) . ? N1 C10 1.416(8) . ? N2 N3 1.377(7) . ? N2 C24 1.422(8) . ? N2 C25 1.453(8) . ? N3 C2 1.392(8) . ? N3 C4 1.455(8) . ? C1 C17 1.528(9) . ? C1 C2 1.535(8) . ? C1 C11 1.551(8) . ? C4 C5 1.437(10) . ? C5 C10 1.390(9) . ? C5 C6 1.421(8) . ? C6 C7 1.354(10) . ? C7 C8 1.391(10) . ? C8 C9 1.386(9) . ? C9 C10 1.389(10) . ? C11 C16 1.373(10) . ? C11 C12 1.386(9) . ? C12 C13 1.399(10) . ? C13 C14 1.349(11) . ? C14 C15 1.383(11) . ? C15 C16 1.401(9) . ? C17 C22 1.374(9) . ? C17 C18 1.395(10) . ? C18 C19 1.403(10) . ? C19 C20 1.363(11) . ? C20 C21 1.382(11) . ? C21 C22 1.394(11) . ? C23 C24 1.454(10) . ? C25 C26 1.509(10) . ? C26 C27 1.526(9) . ? C28 C29 1.495(10) . ? 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 C28 O4 C26 114.2(6) . . ? C2 N1 C10 118.9(6) . . ? N3 N2 C24 119.6(6) . . ? N3 N2 C25 112.0(5) . . ? C24 N2 C25 126.4(6) . . ? N2 N3 C2 122.4(5) . . ? N2 N3 C4 114.5(5) . . ? C2 N3 C4 122.3(5) . . ? C17 C1 C2 111.8(5) . . ? C17 C1 C11 114.8(5) . . ? C2 C1 C11 109.9(5) . . ? N1 C2 N3 123.3(6) . . ? N1 C2 C1 119.7(6) . . ? N3 C2 C1 116.9(6) . . ? O1 C4 C5 129.0(6) . . ? O1 C4 N3 118.5(6) . . ? C5 C4 N3 112.4(6) . . ? C10 C5 C6 119.2(6) . . ? C10 C5 C4 121.4(6) . . ? C6 C5 C4 119.2(6) . . ? C7 C6 C5 120.0(7) . . ? C6 C7 C8 120.5(7) . . ? C9 C8 C7 120.6(7) . . ? C8 C9 C10 119.4(7) . . ? C9 C10 C5 120.3(6) . . ? C9 C10 N1 118.5(6) . . ? C5 C10 N1 121.2(6) . . ? C16 C11 C12 119.7(6) . . ? C16 C11 C1 121.9(6) . . ? C12 C11 C1 118.3(7) . . ? C11 C12 C13 120.0(8) . . ? C14 C13 C12 119.7(7) . . ? C13 C14 C15 121.4(7) . . ? C14 C15 C16 119.0(8) . . ? C11 C16 C15 120.1(7) . . ? C22 C17 C18 118.5(7) . . ? C22 C17 C1 118.8(6) . . ? C18 C17 C1 122.7(6) . . ? C17 C18 C19 119.7(7) . . ? C20 C19 C18 120.7(8) . . ? C19 C20 C21 120.1(7) . . ? C20 C21 C22 119.3(7) . . ? C17 C22 C21 121.6(7) . . ? O2 C24 N2 120.4(7) . . ? O2 C24 C23 123.2(7) . . ? N2 C24 C23 116.5(7) . . ? O3 C25 N2 117.2(6) . . ? O3 C25 C26 123.9(6) . . ? N2 C25 C26 118.6(5) . . ? O4 C26 C25 107.2(5) . . ? O4 C26 C27 105.9(6) . . ? C25 C26 C27 110.3(6) . . ? O5 C28 O4 122.1(7) . . ? O5 C28 C29 126.7(7) . . ? O4 C28 C29 111.2(7) . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.643 _refine_diff_density_min -0.651 _refine_diff_density_rms 0.123 data_19b _database_code_CSD 167264 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H25 N3 O5' _chemical_formula_weight 483.51 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 9.280(2) _cell_length_b 14.826(1) _cell_length_c 18.246(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2510.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 37 _cell_measurement_theta_min 5.41 _cell_measurement_theta_max 12.49 _exptl_crystal_description ovoid _exptl_crystal_colour colourless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.279 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type 'not applied' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'Siemens P4 diffractometer' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 1000 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <2 _diffrn_reflns_number 3166 _diffrn_reflns_av_R_equivalents 0.0211 _diffrn_reflns_av_sigmaI/netI 0.0791 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 25.99 _reflns_number_total 3088 _reflns_number_gt 1838 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XSCANS (Fait, 1991)' _computing_cell_refinement 'XSCANS (Fait, 1991)' _computing_data_reduction 'XSCANS (Fait, 1991)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0638P)^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 9(3) _refine_ls_number_reflns 3088 _refine_ls_number_parameters 301 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1188 _refine_ls_R_factor_gt 0.0588 _refine_ls_wR_factor_ref 0.1444 _refine_ls_wR_factor_gt 0.1180 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.002 _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 0.4370(4) 0.3540(2) 0.9136(2) 0.0506(10) Uani 1 1 d . . . O2 O 0.6856(4) 0.5075(3) 0.7922(2) 0.0563(11) Uani 1 1 d . . . O3 O 0.4064(4) 0.5724(2) 0.95766(19) 0.0436(9) Uani 1 1 d . . . O4 O 0.6468(4) 0.6762(2) 0.96726(19) 0.0455(9) Uani 1 1 d . . . O5 O 0.5228(4) 0.7364(3) 0.8742(2) 0.0521(10) Uani 1 1 d . . . N1 N 0.0826(4) 0.4817(3) 0.8325(2) 0.0337(10) Uani 1 1 d . . . N2 N 0.4673(4) 0.5099(3) 0.8492(2) 0.0311(9) Uani 1 1 d . . . N3 N 0.3310(4) 0.4695(3) 0.8514(2) 0.0305(9) Uani 1 1 d . . . C1 C 0.2330(5) 0.6100(3) 0.7978(2) 0.0302(11) Uani 1 1 d . . . H1B H 0.3120 0.6371 0.8259 0.036 Uiso 1 1 calc R . . C2 C 0.2080(5) 0.5164(3) 0.8298(2) 0.0305(11) Uani 1 1 d . . . C4 C 0.3263(6) 0.3858(3) 0.8895(3) 0.0373(13) Uani 1 1 d . . . C5 C 0.1830(6) 0.3472(3) 0.8924(3) 0.0332(12) Uani 1 1 d . . . C6 C 0.1600(6) 0.2636(3) 0.9263(3) 0.0418(13) Uani 1 1 d . . . H6A H 0.2361 0.2333 0.9485 0.050 Uiso 1 1 calc R . . C7 C 0.0238(7) 0.2267(3) 0.9265(3) 0.0483(15) Uani 1 1 d . . . H7A H 0.0079 0.1710 0.9485 0.058 Uiso 1 1 calc R . . C8 C -0.0890(6) 0.2722(3) 0.8940(3) 0.0475(15) Uani 1 1 d . . . H8A H -0.1803 0.2464 0.8937 0.057 Uiso 1 1 calc R . . C9 C -0.0686(6) 0.3554(4) 0.8621(3) 0.0458(14) Uani 1 1 d . . . H9A H -0.1459 0.3855 0.8406 0.055 Uiso 1 1 calc R . . C10 C 0.0684(5) 0.3948(3) 0.8618(3) 0.0348(12) Uani 1 1 d . . . C11 C 0.2861(3) 0.6013(2) 0.71843(13) 0.0328(11) Uani 1 1 d G . . C12 C 0.4130(3) 0.6447(2) 0.69851(18) 0.0442(14) Uani 1 1 d G . . H12A H 0.4628 0.6792 0.7327 0.053 Uiso 1 1 calc R . . C13 C 0.4654(3) 0.6365(2) 0.6275(2) 0.0604(17) Uani 1 1 d G . . H13A H 0.5503 0.6655 0.6141 0.072 Uiso 1 1 calc R . . C14 C 0.3909(4) 0.5850(3) 0.57632(14) 0.0634(19) Uani 1 1 d G . . H14A H 0.4259 0.5795 0.5288 0.076 Uiso 1 1 calc R . . C15 C 0.2640(4) 0.5416(2) 0.59624(16) 0.0533(16) Uani 1 1 d G . . H15A H 0.2141 0.5072 0.5620 0.064 Uiso 1 1 calc R . . C16 C 0.2116(3) 0.5498(2) 0.66730(18) 0.0414(13) Uani 1 1 d G . . H16A H 0.1267 0.5208 0.6806 0.050 Uiso 1 1 calc R . . C17 C 0.1039(3) 0.67493(19) 0.80420(19) 0.0330(12) Uani 1 1 d G . . C18 C -0.0312(3) 0.65652(18) 0.77493(18) 0.0414(13) Uani 1 1 d G . . H18A H -0.0476 0.6023 0.7507 0.050 Uiso 1 1 calc R . . C19 C -0.1418(3) 0.7192(2) 0.78184(18) 0.0442(14) Uani 1 1 d G . . H19A H -0.2322 0.7069 0.7623 0.053 Uiso 1 1 calc R . . C20 C -0.1173(3) 0.8002(2) 0.8180(2) 0.0525(16) Uani 1 1 d G . . H20A H -0.1913 0.8422 0.8226 0.063 Uiso 1 1 calc R . . C21 C 0.0179(4) 0.81866(18) 0.8473(2) 0.0582(16) Uani 1 1 d G . . H21A H 0.0343 0.8729 0.8715 0.070 Uiso 1 1 calc R . . C22 C 0.1284(3) 0.7560(2) 0.8404(2) 0.0469(15) Uani 1 1 d G . . H22A H 0.2189 0.7683 0.8600 0.056 Uiso 1 1 calc R . . C23 C 0.5100(6) 0.4118(3) 0.7408(3) 0.0450(14) Uani 1 1 d . . . H23A H 0.5851 0.3966 0.7068 0.068 Uiso 1 1 calc R . . H23B H 0.4293 0.4363 0.7146 0.068 Uiso 1 1 calc R . . H23C H 0.4804 0.3585 0.7667 0.068 Uiso 1 1 calc R . . C24 C 0.5645(5) 0.4797(4) 0.7940(3) 0.0378(12) Uani 1 1 d . . . C25 C 0.5003(5) 0.5600(3) 0.9131(3) 0.0337(12) Uani 1 1 d . . . C26 C 0.6531(5) 0.5927(3) 0.9254(3) 0.0412(13) Uani 1 1 d . . . H26A H 0.7019 0.6025 0.8784 0.049 Uiso 1 1 calc R . . C27 C 0.7341(7) 0.5251(4) 0.9708(4) 0.071(2) Uani 1 1 d . . . H27A H 0.8308 0.5460 0.9785 0.106 Uiso 1 1 calc R . . H27B H 0.7363 0.4682 0.9457 0.106 Uiso 1 1 calc R . . H27C H 0.6869 0.5179 1.0173 0.106 Uiso 1 1 calc R . . C28 C 0.5798(6) 0.7453(4) 0.9335(3) 0.0457(14) Uani 1 1 d . . . C29 C 0.5830(8) 0.8281(4) 0.9789(4) 0.0668(19) Uani 1 1 d . . . H29A H 0.5346 0.8760 0.9535 0.100 Uiso 1 1 calc R . . H29B H 0.6813 0.8451 0.9879 0.100 Uiso 1 1 calc R . . H29C H 0.5354 0.8168 1.0247 0.100 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.046(2) 0.045(2) 0.061(2) 0.014(2) -0.011(2) 0.002(2) O2 0.034(2) 0.076(3) 0.059(2) -0.022(2) 0.0077(19) 0.000(2) O3 0.040(2) 0.048(2) 0.043(2) -0.0040(19) 0.0095(19) -0.0053(19) O4 0.049(2) 0.043(2) 0.045(2) -0.004(2) -0.006(2) -0.005(2) O5 0.048(2) 0.054(2) 0.054(2) 0.007(2) -0.010(2) -0.007(2) N1 0.030(2) 0.031(2) 0.040(2) 0.005(2) 0.004(2) -0.0043(19) N2 0.024(2) 0.032(2) 0.037(2) -0.003(2) -0.0008(18) -0.0039(19) N3 0.024(2) 0.030(2) 0.037(2) -0.001(2) -0.0007(19) -0.0014(18) C1 0.024(2) 0.032(3) 0.034(3) 0.000(2) -0.002(2) -0.004(2) C2 0.037(3) 0.030(3) 0.024(2) -0.003(2) 0.001(2) 0.003(2) C4 0.040(3) 0.035(3) 0.038(3) 0.005(3) -0.005(3) 0.001(3) C5 0.040(3) 0.031(3) 0.029(3) -0.001(2) 0.006(2) -0.004(2) C6 0.054(3) 0.031(3) 0.041(3) 0.003(3) -0.001(3) -0.001(3) C7 0.070(4) 0.030(3) 0.045(3) 0.006(3) 0.010(3) -0.009(3) C8 0.052(4) 0.032(3) 0.059(4) -0.002(3) 0.012(3) -0.014(3) C9 0.037(3) 0.043(3) 0.057(4) -0.005(3) 0.007(3) -0.001(3) C10 0.037(3) 0.030(3) 0.037(3) -0.004(2) 0.004(2) -0.005(2) C11 0.034(3) 0.030(2) 0.034(3) 0.001(2) -0.001(2) 0.006(2) C12 0.040(3) 0.036(3) 0.056(3) 0.004(3) 0.008(3) -0.007(3) C13 0.063(4) 0.058(4) 0.060(4) 0.017(3) 0.021(3) 0.002(4) C14 0.093(5) 0.057(4) 0.040(3) 0.008(3) 0.016(4) 0.032(4) C15 0.062(4) 0.049(3) 0.048(3) -0.005(3) -0.010(3) 0.019(3) C16 0.039(3) 0.042(3) 0.043(3) 0.002(3) -0.007(3) 0.006(3) C17 0.037(3) 0.030(3) 0.032(3) 0.007(2) -0.001(2) 0.002(2) C18 0.032(3) 0.038(3) 0.054(3) 0.002(3) -0.001(3) 0.003(3) C19 0.036(3) 0.045(3) 0.051(3) 0.011(3) 0.004(3) 0.004(3) C20 0.051(4) 0.049(4) 0.058(4) 0.006(3) 0.006(3) 0.017(3) C21 0.068(4) 0.035(3) 0.072(4) -0.010(3) -0.007(4) 0.011(3) C22 0.048(3) 0.035(3) 0.058(4) -0.002(3) 0.002(3) 0.004(3) C23 0.046(3) 0.036(3) 0.053(3) -0.014(3) 0.002(3) 0.006(3) C24 0.028(3) 0.044(3) 0.041(3) -0.003(3) 0.001(2) 0.005(3) C25 0.035(3) 0.026(2) 0.040(3) 0.010(2) -0.004(3) 0.001(2) C26 0.035(3) 0.046(3) 0.043(3) -0.009(3) -0.006(3) -0.001(3) C27 0.061(4) 0.050(4) 0.100(5) -0.020(4) -0.030(4) 0.011(3) C28 0.048(3) 0.040(3) 0.050(3) 0.004(3) -0.004(3) -0.015(3) C29 0.087(5) 0.039(3) 0.074(4) -0.004(3) -0.010(4) -0.001(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 O1 C4 1.212(6) . ? O2 C24 1.197(6) . ? O3 C25 1.206(6) . ? O4 C28 1.348(6) . ? O4 C26 1.456(6) . ? O5 C28 1.211(6) . ? N1 C2 1.273(6) . ? N1 C10 1.402(6) . ? N2 N3 1.400(5) . ? N2 C25 1.416(6) . ? N2 C24 1.424(6) . ? N3 C2 1.393(6) . ? N3 C4 1.423(6) . ? C1 C2 1.523(7) . ? C1 C11 1.535(5) . ? C1 C17 1.541(5) . ? C4 C5 1.449(7) . ? C5 C10 1.392(7) . ? C5 C6 1.401(7) . ? C6 C7 1.377(7) . ? C7 C8 1.379(8) . ? C8 C9 1.378(7) . ? C9 C10 1.399(7) . ? C11 C12 1.3900 . ? C11 C16 1.3900 . ? C12 C13 1.3900 . ? C13 C14 1.3900 . ? C14 C15 1.3900 . ? C15 C16 1.3900 . ? C17 C18 1.3900 . ? C17 C22 1.3900 . ? C18 C19 1.3900 . ? C19 C20 1.3900 . ? C20 C21 1.3900 . ? C21 C22 1.3900 . ? C23 C24 1.487(7) . ? C25 C26 1.515(7) . ? C26 C27 1.502(8) . ? C28 C29 1.481(8) . ? 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 C28 O4 C26 115.1(4) . . ? C2 N1 C10 118.1(4) . . ? N3 N2 C25 113.3(4) . . ? N3 N2 C24 117.2(4) . . ? C25 N2 C24 127.6(4) . . ? C2 N3 N2 121.2(4) . . ? C2 N3 C4 123.3(4) . . ? N2 N3 C4 114.5(4) . . ? C2 C1 C11 109.5(4) . . ? C2 C1 C17 114.9(4) . . ? C11 C1 C17 111.9(3) . . ? N1 C2 N3 122.4(4) . . ? N1 C2 C1 121.5(4) . . ? N3 C2 C1 116.0(4) . . ? O1 C4 N3 119.4(5) . . ? O1 C4 C5 127.6(5) . . ? N3 C4 C5 113.0(4) . . ? C10 C5 C6 120.6(5) . . ? C10 C5 C4 119.1(4) . . ? C6 C5 C4 120.3(5) . . ? C7 C6 C5 119.5(5) . . ? C6 C7 C8 120.1(5) . . ? C9 C8 C7 121.0(5) . . ? C8 C9 C10 119.9(5) . . ? C5 C10 C9 118.8(5) . . ? C5 C10 N1 123.2(4) . . ? C9 C10 N1 118.0(5) . . ? C12 C11 C16 120.0 . . ? C12 C11 C1 118.7(3) . . ? C16 C11 C1 121.3(3) . . ? C11 C12 C13 120.0 . . ? C14 C13 C12 120.0 . . ? C13 C14 C15 120.0 . . ? C16 C15 C14 120.0 . . ? C15 C16 C11 120.0 . . ? C18 C17 C22 120.0 . . ? C18 C17 C1 123.4(3) . . ? C22 C17 C1 116.6(3) . . ? C17 C18 C19 120.0 . . ? C20 C19 C18 120.0 . . ? C19 C20 C21 120.0 . . ? C20 C21 C22 120.0 . . ? C21 C22 C17 120.0 . . ? O2 C24 N2 120.4(5) . . ? O2 C24 C23 122.3(5) . . ? N2 C24 C23 117.3(4) . . ? O3 C25 N2 118.7(4) . . ? O3 C25 C26 121.8(5) . . ? N2 C25 C26 119.5(5) . . ? O4 C26 C27 107.3(4) . . ? O4 C26 C25 108.2(4) . . ? C27 C26 C25 109.7(5) . . ? O5 C28 O4 121.8(5) . . ? O5 C28 C29 126.8(6) . . ? O4 C28 C29 111.4(5) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.203 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.049