# Electronic Supplementary Material (ESI) for Analyst # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'The Analyst' _journal_coden_cambridge 0091 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email wschung@nctu.edu.tw _publ_contact_author_name 'Wen-Sheng Chung' loop_ _publ_author_name 'I-Ting Ho' 'Ting-Ling Lai' 'Ren-Tsung Wu' 'Ming-Tsung Tsai' ; Chun-Ming Wu ; 'Gene-Hsiang Lee' 'Wen-Sheng Chung' data_110634lt_0m _database_code_depnum_ccdc_archive 'CCDC 870923' #TrackingRef '- L1 (110634) WSChung_20120310.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H23 N3 O4' _chemical_formula_weight 405.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.933(3) _cell_length_b 11.085(6) _cell_length_c 15.588(8) _cell_angle_alpha 93.50(2) _cell_angle_beta 92.85(2) _cell_angle_gamma 93.01(2) _cell_volume 1020.4(9) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3774 _cell_measurement_theta_min 3.1080 _cell_measurement_theta_max 25.1832 _exptl_crystal_description Tabullar _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 428 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7632 _exptl_absorpt_correction_T_max 0.9486 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 13644 _diffrn_reflns_av_R_equivalents 0.0764 _diffrn_reflns_av_sigmaI/netI 0.0933 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.31 _diffrn_reflns_theta_max 26.56 _reflns_number_total 4137 _reflns_number_gt 2093 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.34A (Bruker AXS, 2006)' _computing_data_reduction 'SAINT V7.34A (Bruker AXS, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _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^)+(0.1530P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4137 _refine_ls_number_parameters 275 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1373 _refine_ls_R_factor_gt 0.0763 _refine_ls_wR_factor_ref 0.2611 _refine_ls_wR_factor_gt 0.2076 _refine_ls_goodness_of_fit_ref 0.973 _refine_ls_restrained_S_all 0.973 _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 1.0562(4) 0.5826(2) 0.21645(14) 0.0527(7) Uani 1 1 d . . . O2 O -0.1334(5) 1.0107(2) -0.28530(17) 0.0677(8) Uani 1 1 d . . . O3 O 0.2671(4) 0.73820(19) -0.13394(14) 0.0478(6) Uani 1 1 d . . . O4 O 0.4214(4) 0.6001(2) -0.06034(16) 0.0555(7) Uani 1 1 d . . . N1 N 0.7927(4) 0.7605(2) 0.00172(16) 0.0389(7) Uani 1 1 d . . . N2 N 1.1200(5) 0.7815(3) 0.06581(18) 0.0501(8) Uani 1 1 d . . . N3 N 0.9814(5) 0.8359(2) 0.01617(18) 0.0480(8) Uani 1 1 d . . . C1 C 1.4977(9) 0.3311(4) 0.5281(3) 0.0857(15) Uani 1 1 d . . . H1A H 1.6168 0.3845 0.5070 0.129 Uiso 1 1 calc R . . H1B H 1.5646 0.2784 0.5695 0.129 Uiso 1 1 calc R . . H1C H 1.3865 0.3801 0.5563 0.129 Uiso 1 1 calc R . . C2 C 1.3804(6) 0.2531(3) 0.4520(2) 0.0552(10) Uani 1 1 d . . . C3 C 1.2950(6) 0.3373(3) 0.3863(2) 0.0440(9) Uani 1 1 d . . . C4 C 1.1001(6) 0.4004(3) 0.3980(2) 0.0541(10) Uani 1 1 d . . . H4 H 1.0175 0.3879 0.4477 0.065 Uiso 1 1 calc R . . C5 C 1.0242(6) 0.4789(3) 0.3410(2) 0.0537(9) Uani 1 1 d . . . H5 H 0.8888 0.5187 0.3504 0.064 Uiso 1 1 calc R . . C6 C 1.1435(6) 0.5008(3) 0.2693(2) 0.0440(8) Uani 1 1 d . . . C7 C 1.1494(6) 0.5880(3) 0.1345(2) 0.0523(9) Uani 1 1 d . . . H7A H 1.1392 0.5065 0.1045 0.063 Uiso 1 1 calc R . . H7B H 1.3109 0.6160 0.1416 0.063 Uiso 1 1 calc R . . C8 C 1.0254(6) 0.6716(3) 0.0834(2) 0.0437(8) Uani 1 1 d . . . C9 C 0.8155(6) 0.6576(3) 0.0431(2) 0.0446(9) Uani 1 1 d . . . H9 H 0.7091 0.5907 0.0439 0.054 Uiso 1 1 calc R . . C10 C 0.6134(6) 0.7960(3) -0.0522(2) 0.0391(8) Uani 1 1 d . . . C11 C 0.6091(6) 0.9095(3) -0.07854(19) 0.0404(8) Uani 1 1 d . . . H11 H 0.7282 0.9675 -0.0604 0.048 Uiso 1 1 calc R . . C12 C 0.4273(6) 0.9428(3) -0.1332(2) 0.0403(8) Uani 1 1 d . . . C13 C 0.4052(6) 1.0589(3) -0.1621(2) 0.0467(9) Uani 1 1 d . . . H13 H 0.5196 1.1204 -0.1459 0.056 Uiso 1 1 calc R . . C14 C 0.2236(6) 1.0858(3) -0.2129(2) 0.0479(9) Uani 1 1 d . . . H14 H 0.2105 1.1652 -0.2318 0.058 Uiso 1 1 calc R . . C15 C 0.0567(6) 0.9945(3) -0.2369(2) 0.0487(9) Uani 1 1 d . . . C16 C -0.1691(8) 1.1290(4) -0.3127(3) 0.0725(12) Uani 1 1 d . . . H16A H -0.1691 1.1863 -0.2623 0.109 Uiso 1 1 calc R . . H16B H -0.3149 1.1284 -0.3452 0.109 Uiso 1 1 calc R . . H16C H -0.0478 1.1536 -0.3495 0.109 Uiso 1 1 calc R . . C17 C 1.5484(7) 0.1680(4) 0.4155(3) 0.0655(11) Uani 1 1 d . . . H17A H 1.4805 0.1235 0.3635 0.098 Uiso 1 1 calc R . . H17B H 1.5888 0.1106 0.4584 0.098 Uiso 1 1 calc R . . H17C H 1.6846 0.2148 0.4011 0.098 Uiso 1 1 calc R . . C18 C 0.2577(6) 0.8540(3) -0.1594(2) 0.0420(8) Uani 1 1 d . . . C19 C 0.4338(6) 0.7029(3) -0.0795(2) 0.0422(8) Uani 1 1 d . . . C20 C 0.0739(6) 0.8779(3) -0.2109(2) 0.0496(9) Uani 1 1 d . . . H20 H -0.0389 0.8161 -0.2284 0.059 Uiso 1 1 calc R . . C21 C 1.3391(6) 0.4427(3) 0.2569(2) 0.0533(10) Uani 1 1 d . . . H21 H 1.4243 0.4577 0.2083 0.064 Uiso 1 1 calc R . . C22 C 1.4110(6) 0.3629(3) 0.3149(2) 0.0529(9) Uani 1 1 d . . . H22 H 1.5470 0.3237 0.3053 0.064 Uiso 1 1 calc R . . C23 C 1.1823(8) 0.1749(4) 0.4836(3) 0.0808(14) Uani 1 1 d . . . H23A H 1.0767 0.2273 0.5120 0.121 Uiso 1 1 calc R . . H23B H 1.2407 0.1190 0.5246 0.121 Uiso 1 1 calc R . . H23C H 1.1036 0.1286 0.4344 0.121 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 0.0586(16) 0.0543(15) 0.0477(13) 0.0128(11) 0.0022(12) 0.0180(12) O2 0.0682(18) 0.0631(18) 0.0694(17) 0.0086(14) -0.0278(15) 0.0061(14) O3 0.0480(15) 0.0358(13) 0.0577(14) 0.0060(11) -0.0110(12) -0.0052(11) O4 0.0589(17) 0.0310(13) 0.0748(16) 0.0100(11) -0.0109(13) -0.0104(11) N1 0.0408(16) 0.0309(15) 0.0446(15) 0.0073(11) -0.0016(13) -0.0049(12) N2 0.0436(18) 0.0486(18) 0.0576(18) 0.0136(14) -0.0089(14) -0.0030(14) N3 0.0387(17) 0.0453(17) 0.0585(17) 0.0103(14) -0.0073(14) -0.0100(14) C1 0.112(4) 0.078(3) 0.064(3) 0.002(2) -0.041(3) 0.027(3) C2 0.051(2) 0.058(2) 0.057(2) 0.0108(18) -0.0107(18) 0.0059(19) C3 0.039(2) 0.045(2) 0.0465(19) 0.0071(15) -0.0133(16) 0.0021(16) C4 0.049(2) 0.065(3) 0.051(2) 0.0155(18) 0.0016(18) 0.0113(19) C5 0.044(2) 0.063(2) 0.057(2) 0.0139(18) 0.0016(18) 0.0132(18) C6 0.044(2) 0.042(2) 0.0459(19) 0.0078(15) -0.0084(16) 0.0081(16) C7 0.058(2) 0.051(2) 0.049(2) 0.0096(16) -0.0043(18) 0.0083(18) C8 0.047(2) 0.0396(19) 0.0442(18) 0.0038(15) 0.0011(17) -0.0003(16) C9 0.052(2) 0.0326(18) 0.0494(19) 0.0082(14) -0.0008(18) -0.0002(15) C10 0.042(2) 0.0336(18) 0.0414(17) 0.0049(14) 0.0021(15) -0.0016(15) C11 0.041(2) 0.0338(18) 0.0450(18) 0.0044(14) 0.0003(16) -0.0074(14) C12 0.042(2) 0.0389(19) 0.0398(17) 0.0059(14) 0.0003(16) -0.0020(15) C13 0.050(2) 0.0386(19) 0.0501(19) 0.0073(15) -0.0022(17) -0.0078(16) C14 0.054(2) 0.043(2) 0.0470(19) 0.0113(15) -0.0075(18) 0.0022(17) C15 0.055(2) 0.053(2) 0.0369(18) 0.0026(16) -0.0069(17) 0.0041(18) C16 0.081(3) 0.068(3) 0.069(3) 0.023(2) -0.021(2) 0.009(2) C17 0.055(2) 0.060(3) 0.082(3) 0.020(2) -0.012(2) 0.010(2) C18 0.047(2) 0.0407(19) 0.0382(17) 0.0033(14) 0.0018(16) -0.0015(16) C19 0.040(2) 0.0367(19) 0.0488(19) 0.0033(15) -0.0007(16) -0.0009(15) C20 0.050(2) 0.048(2) 0.049(2) -0.0010(16) -0.0097(17) -0.0014(17) C21 0.053(2) 0.061(2) 0.048(2) 0.0123(18) 0.0027(18) 0.0112(19) C22 0.046(2) 0.060(2) 0.055(2) 0.0079(18) -0.0035(18) 0.0171(18) C23 0.073(3) 0.088(3) 0.088(3) 0.041(3) 0.012(3) 0.018(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 O1 C6 1.366(4) . ? O1 C7 1.421(4) . ? O2 C15 1.352(4) . ? O2 C16 1.427(5) . ? O3 C19 1.360(4) . ? O3 C18 1.370(4) . ? O4 C19 1.195(4) . ? N1 C9 1.353(4) . ? N1 N3 1.363(3) . ? N1 C10 1.410(4) . ? N2 N3 1.298(4) . ? N2 C8 1.362(4) . ? C1 C2 1.540(5) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.513(5) . ? C2 C17 1.515(6) . ? C2 C23 1.543(5) . ? C3 C22 1.373(5) . ? C3 C4 1.396(5) . ? C4 C5 1.359(5) . ? C4 H4 0.9500 . ? C5 C6 1.379(5) . ? C5 H5 0.9500 . ? C6 C21 1.373(5) . ? C7 C8 1.462(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.364(5) . ? C9 H9 0.9500 . ? C10 C11 1.349(4) . ? C10 C19 1.472(4) . ? C11 C12 1.419(4) . ? C11 H11 0.9500 . ? C12 C18 1.398(4) . ? C12 C13 1.400(5) . ? C13 C14 1.362(5) . ? C13 H13 0.9500 . ? C14 C15 1.399(5) . ? C14 H14 0.9500 . ? C15 C20 1.385(5) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C20 1.368(5) . ? C20 H20 0.9500 . ? C21 C22 1.372(5) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? 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 C6 O1 C7 116.3(3) . . ? C15 O2 C16 118.2(3) . . ? C19 O3 C18 123.1(2) . . ? C9 N1 N3 110.7(3) . . ? C9 N1 C10 130.3(3) . . ? N3 N1 C10 119.0(3) . . ? N3 N2 C8 109.8(3) . . ? N2 N3 N1 106.6(3) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 C17 112.2(3) . . ? C3 C2 C1 108.0(3) . . ? C17 C2 C1 108.7(3) . . ? C3 C2 C23 110.4(3) . . ? C17 C2 C23 107.5(3) . . ? C1 C2 C23 109.9(4) . . ? C22 C3 C4 115.8(3) . . ? C22 C3 C2 122.5(3) . . ? C4 C3 C2 121.5(3) . . ? C5 C4 C3 122.4(3) . . ? C5 C4 H4 118.8 . . ? C3 C4 H4 118.8 . . ? C4 C5 C6 120.0(4) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? O1 C6 C21 125.1(3) . . ? O1 C6 C5 115.8(3) . . ? C21 C6 C5 119.1(3) . . ? O1 C7 C8 109.5(3) . . ? O1 C7 H7A 109.8 . . ? C8 C7 H7A 109.8 . . ? O1 C7 H7B 109.8 . . ? C8 C7 H7B 109.8 . . ? H7A C7 H7B 108.2 . . ? N2 C8 C9 108.4(3) . . ? N2 C8 C7 121.5(3) . . ? C9 C8 C7 130.0(3) . . ? N1 C9 C8 104.5(3) . . ? N1 C9 H9 127.7 . . ? C8 C9 H9 127.7 . . ? C11 C10 N1 121.4(3) . . ? C11 C10 C19 121.7(3) . . ? N1 C10 C19 116.9(3) . . ? C10 C11 C12 120.3(3) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C18 C12 C13 117.7(3) . . ? C18 C12 C11 117.9(3) . . ? C13 C12 C11 124.4(3) . . ? C14 C13 C12 121.6(3) . . ? C14 C13 H13 119.2 . . ? C12 C13 H13 119.2 . . ? C13 C14 C15 118.8(3) . . ? C13 C14 H14 120.6 . . ? C15 C14 H14 120.6 . . ? O2 C15 C20 114.2(3) . . ? O2 C15 C14 124.3(3) . . ? C20 C15 C14 121.5(3) . . ? O2 C16 H16A 109.5 . . ? O2 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O2 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C2 C17 H17A 109.5 . . ? C2 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C2 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C20 C18 O3 116.6(3) . . ? C20 C18 C12 122.2(3) . . ? O3 C18 C12 121.2(3) . . ? O4 C19 O3 117.0(3) . . ? O4 C19 C10 127.2(3) . . ? O3 C19 C10 115.8(3) . . ? C18 C20 C15 118.3(3) . . ? C18 C20 H20 120.9 . . ? C15 C20 H20 120.9 . . ? C22 C21 C6 119.8(3) . . ? C22 C21 H21 120.1 . . ? C6 C21 H21 120.1 . . ? C21 C22 C3 122.8(4) . . ? C21 C22 H22 118.6 . . ? C3 C22 H22 118.6 . . ? C2 C23 H23A 109.5 . . ? C2 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C2 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 26.56 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.373 _refine_diff_density_min -0.455 _refine_diff_density_rms 0.132 # Attachment '- L3 (IC12713)_WSChung.cif' data_ic12713 _database_code_depnum_ccdc_archive 'CCDC 870924' #TrackingRef '- L3 (IC12713)_WSChung.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H25 N3 O5' _chemical_formula_weight 447.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.7298(4) _cell_length_b 11.4420(8) _cell_length_c 17.7012(13) _cell_angle_alpha 96.531(2) _cell_angle_beta 96.165(2) _cell_angle_gamma 93.056(2) _cell_volume 1143.77(14) _cell_formula_units_Z 2 _cell_measurement_temperature 220(2) _cell_measurement_reflns_used 1336 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 21.24 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.299 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9470 _exptl_absorpt_correction_T_max 0.9963 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 220(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 'BRUKER SMART APEXCCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10379 _diffrn_reflns_av_R_equivalents 0.0393 _diffrn_reflns_av_sigmaI/netI 0.0551 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.17 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4027 _reflns_number_gt 2811 _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 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0969P)^2^+0.5312P] 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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.037(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4027 _refine_ls_number_parameters 303 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1129 _refine_ls_R_factor_gt 0.0805 _refine_ls_wR_factor_ref 0.2179 _refine_ls_wR_factor_gt 0.1918 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.106 _refine_ls_shift/su_max 0.004 _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 0.3687(5) 0.3449(2) 0.50779(16) 0.0569(8) Uani 1 1 d . . . O2 O 0.5572(4) 0.1089(2) 0.33060(14) 0.0481(7) Uani 1 1 d . . . O3 O 0.8496(4) 0.23070(19) 0.31243(13) 0.0431(6) Uani 1 1 d . . . O4 O 1.4483(5) 0.4791(3) 0.24715(18) 0.0674(9) Uani 1 1 d . . . O5 O -0.0048(5) 0.2112(2) 0.75264(14) 0.0538(7) Uani 1 1 d . . . N1 N 0.1765(5) 0.1347(2) 0.52257(15) 0.0336(7) Uani 1 1 d . . . N2 N -0.0556(5) 0.1458(2) 0.51108(17) 0.0409(7) Uani 1 1 d . . . N3 N -0.1388(5) 0.1355(3) 0.57619(18) 0.0450(8) Uani 1 1 d . . . C1 C 0.2418(6) 0.1180(3) 0.59557(19) 0.0375(8) Uani 1 1 d . . . H1 H 0.3945 0.1083 0.6182 0.045 Uiso 1 1 calc R . . C2 C 0.0414(6) 0.1183(3) 0.6298(2) 0.0377(8) Uani 1 1 d . . . C3 C 0.3189(6) 0.1431(3) 0.46090(19) 0.0401(8) Uani 1 1 d . . . H3A H 0.2217 0.1196 0.4120 0.048 Uiso 1 1 calc R . . H3B H 0.4448 0.0887 0.4653 0.048 Uiso 1 1 calc R . . C4 C 0.4261(6) 0.2670(3) 0.46185(19) 0.0371(8) Uani 1 1 d . . . C5 C 0.6599(6) 0.2033(3) 0.35085(19) 0.0372(8) Uani 1 1 d . . . C6 C 0.6049(6) 0.2923(3) 0.41103(18) 0.0349(8) Uani 1 1 d . . . C7 C 0.7237(7) 0.3987(3) 0.42182(19) 0.0416(9) Uani 1 1 d . . . H7 H 0.6818 0.4563 0.4593 0.050 Uiso 1 1 calc R . . C8 C 0.9087(6) 0.4274(3) 0.37908(19) 0.0377(8) Uani 1 1 d . . . C9 C 0.9714(6) 0.3400(3) 0.32485(19) 0.0386(8) Uani 1 1 d . . . C10 C 1.1506(6) 0.3581(3) 0.2818(2) 0.0485(9) Uani 1 1 d . . . H10 H 1.1906 0.2973 0.2461 0.058 Uiso 1 1 calc R . . C11 C 1.2733(6) 0.4679(3) 0.2916(2) 0.0467(9) Uani 1 1 d . . . C12 C 1.2174(7) 0.5572(3) 0.3449(2) 0.0483(9) Uani 1 1 d . . . H12 H 1.3013 0.6312 0.3514 0.058 Uiso 1 1 calc R . . C13 C 1.0385(7) 0.5363(3) 0.3878(2) 0.0469(9) Uani 1 1 d . . . H13 H 1.0014 0.5968 0.4243 0.056 Uiso 1 1 calc R . . C14 C 1.5780(8) 0.5904(4) 0.2528(3) 0.0743(14) Uani 1 1 d . . . H14A H 1.4749 0.6486 0.2350 0.111 Uiso 1 1 calc R . . H14B H 1.7066 0.5834 0.2214 0.111 Uiso 1 1 calc R . . H14C H 1.6405 0.6148 0.3057 0.111 Uiso 1 1 calc R . . C15 C 0.0008(7) 0.0992(3) 0.7084(2) 0.0495(10) Uani 1 1 d . . . H15A H -0.1489 0.0532 0.7078 0.059 Uiso 1 1 calc R . . H15B H 0.1271 0.0552 0.7310 0.059 Uiso 1 1 calc R . . C16 C -0.0759(7) 0.2137(3) 0.8245(2) 0.0462(9) Uani 1 1 d . . . C17 C -0.1326(10) 0.1172(4) 0.8590(3) 0.0753(15) Uani 1 1 d . . . H17 H -0.1207 0.0410 0.8342 0.090 Uiso 1 1 calc R . . C18 C -0.2078(11) 0.1323(4) 0.9309(3) 0.0843(16) Uani 1 1 d . . . H18 H -0.2461 0.0646 0.9538 0.101 Uiso 1 1 calc R . . C19 C -0.2297(7) 0.2395(4) 0.9706(2) 0.0526(10) Uani 1 1 d . . . C20 C -0.1673(7) 0.3360(4) 0.9346(2) 0.0556(11) Uani 1 1 d . . . H20 H -0.1787 0.4123 0.9595 0.067 Uiso 1 1 calc R . . C21 C -0.0889(7) 0.3233(3) 0.8634(2) 0.0532(10) Uani 1 1 d . . . H21 H -0.0439 0.3906 0.8412 0.064 Uiso 1 1 calc R . . C22 C -0.3238(8) 0.2548(5) 1.0486(3) 0.0708(13) Uani 1 1 d . . . C23 C -0.5748(10) 0.2441(12) 1.0397(4) 0.249(7) Uani 1 1 d . . . H23A H -0.6300 0.2300 1.0879 0.374 Uiso 1 1 calc R . . H23B H -0.6300 0.1787 1.0010 0.374 Uiso 1 1 calc R . . H23C H -0.6348 0.3164 1.0240 0.374 Uiso 1 1 calc R . . C24 C -0.2115(12) 0.3583(6) 1.0992(3) 0.116(2) Uani 1 1 d . . . H24A H -0.2727 0.4295 1.0822 0.174 Uiso 1 1 calc R . . H24B H -0.0427 0.3608 1.0974 0.174 Uiso 1 1 calc R . . H24C H -0.2453 0.3527 1.1512 0.174 Uiso 1 1 calc R . . C25 C -0.2398(17) 0.1532(6) 1.0964(4) 0.145(3) Uani 1 1 d . . . H25A H -0.2765 0.1703 1.1486 0.217 Uiso 1 1 calc R . . H25B H -0.0713 0.1482 1.0965 0.217 Uiso 1 1 calc R . . H25C H -0.3200 0.0787 1.0735 0.217 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 0.081(2) 0.0285(14) 0.0643(18) -0.0068(12) 0.0350(15) 0.0022(12) O2 0.0616(16) 0.0341(14) 0.0461(15) -0.0080(11) 0.0128(12) -0.0047(12) O3 0.0537(15) 0.0340(13) 0.0404(14) -0.0059(10) 0.0119(12) -0.0002(11) O4 0.0560(17) 0.0623(19) 0.084(2) 0.0002(15) 0.0248(16) -0.0078(14) O5 0.0808(19) 0.0381(15) 0.0438(16) -0.0029(11) 0.0244(14) -0.0021(13) N1 0.0380(16) 0.0273(14) 0.0347(16) -0.0001(11) 0.0054(12) 0.0018(11) N2 0.0397(17) 0.0362(16) 0.0447(19) 0.0008(13) 0.0002(14) 0.0004(13) N3 0.0410(17) 0.0372(17) 0.056(2) -0.0024(14) 0.0099(15) 0.0006(13) C1 0.044(2) 0.0308(18) 0.037(2) -0.0019(14) 0.0038(16) 0.0059(14) C2 0.044(2) 0.0268(17) 0.042(2) 0.0001(14) 0.0093(17) 0.0020(14) C3 0.054(2) 0.0327(18) 0.0343(19) 0.0013(14) 0.0106(17) 0.0026(16) C4 0.049(2) 0.0272(17) 0.0341(19) 0.0004(14) -0.0002(16) 0.0081(15) C5 0.048(2) 0.0290(18) 0.0336(19) 0.0004(14) 0.0030(16) 0.0029(15) C6 0.0459(19) 0.0258(17) 0.0326(18) 0.0031(13) 0.0031(15) 0.0049(14) C7 0.061(2) 0.0298(18) 0.0340(19) 0.0010(14) 0.0062(17) 0.0094(16) C8 0.047(2) 0.0305(18) 0.036(2) 0.0036(14) 0.0043(16) 0.0055(15) C9 0.0412(19) 0.0339(19) 0.039(2) 0.0040(15) -0.0009(16) 0.0025(15) C10 0.049(2) 0.048(2) 0.047(2) -0.0023(17) 0.0092(18) 0.0029(18) C11 0.038(2) 0.052(2) 0.051(2) 0.0082(18) 0.0078(18) 0.0024(17) C12 0.046(2) 0.040(2) 0.058(2) 0.0080(18) 0.0012(19) -0.0029(17) C13 0.058(2) 0.0295(19) 0.051(2) 0.0005(16) 0.0059(19) -0.0013(16) C14 0.057(3) 0.069(3) 0.100(4) 0.016(3) 0.021(3) -0.008(2) C15 0.065(3) 0.036(2) 0.048(2) -0.0025(16) 0.0191(19) 0.0013(17) C16 0.055(2) 0.044(2) 0.040(2) 0.0019(16) 0.0128(18) 0.0005(17) C17 0.135(5) 0.037(2) 0.058(3) 0.0002(19) 0.041(3) -0.002(2) C18 0.145(5) 0.050(3) 0.060(3) 0.002(2) 0.041(3) -0.019(3) C19 0.053(2) 0.061(3) 0.042(2) -0.0067(18) 0.0140(18) -0.0110(19) C20 0.063(3) 0.049(2) 0.051(2) -0.0119(18) 0.013(2) -0.0006(19) C21 0.070(3) 0.041(2) 0.048(2) -0.0015(17) 0.017(2) -0.0073(19) C22 0.071(3) 0.090(4) 0.049(3) -0.007(2) 0.023(2) -0.023(3) C23 0.048(4) 0.61(2) 0.079(5) -0.045(8) 0.033(3) 0.003(7) C24 0.143(6) 0.141(6) 0.058(3) -0.020(3) 0.040(4) -0.023(5) C25 0.244(10) 0.125(6) 0.076(4) 0.017(4) 0.063(5) 0.000(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 C4 1.219(4) . ? O2 C5 1.200(4) . ? O3 C9 1.382(4) . ? O3 C5 1.384(4) . ? O4 C11 1.349(4) . ? O4 C14 1.428(5) . ? O5 C16 1.375(4) . ? O5 C15 1.428(4) . ? N1 N2 1.339(4) . ? N1 C1 1.344(4) . ? N1 C3 1.440(4) . ? N2 N3 1.308(4) . ? N3 C2 1.363(4) . ? C1 C2 1.355(5) . ? C2 C15 1.474(5) . ? C3 C4 1.512(4) . ? C4 C6 1.472(5) . ? C5 C6 1.460(5) . ? C6 C7 1.347(5) . ? C7 C8 1.413(5) . ? C8 C9 1.395(5) . ? C8 C13 1.401(5) . ? C9 C10 1.363(5) . ? C10 C11 1.390(5) . ? C11 C12 1.385(5) . ? C12 C13 1.367(5) . ? C16 C17 1.362(5) . ? C16 C21 1.370(5) . ? C17 C18 1.382(6) . ? C18 C19 1.361(6) . ? C19 C20 1.385(6) . ? C19 C22 1.530(5) . ? C20 C21 1.379(5) . ? C22 C23 1.427(7) . ? C22 C24 1.474(7) . ? C22 C25 1.580(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 C9 O3 C5 122.6(3) . . ? C11 O4 C14 118.6(3) . . ? C16 O5 C15 118.1(3) . . ? N2 N1 C1 110.5(3) . . ? N2 N1 C3 120.2(3) . . ? C1 N1 C3 129.3(3) . . ? N3 N2 N1 107.1(3) . . ? N2 N3 C2 109.1(3) . . ? N1 C1 C2 105.6(3) . . ? C1 C2 N3 107.7(3) . . ? C1 C2 C15 130.5(3) . . ? N3 C2 C15 121.7(3) . . ? N1 C3 C4 111.6(3) . . ? O1 C4 C6 120.5(3) . . ? O1 C4 C3 118.6(3) . . ? C6 C4 C3 120.8(3) . . ? O2 C5 O3 116.2(3) . . ? O2 C5 C6 127.0(3) . . ? O3 C5 C6 116.7(3) . . ? C7 C6 C5 119.6(3) . . ? C7 C6 C4 119.1(3) . . ? C5 C6 C4 121.3(3) . . ? C6 C7 C8 122.7(3) . . ? C9 C8 C13 117.1(3) . . ? C9 C8 C7 117.7(3) . . ? C13 C8 C7 125.2(3) . . ? C10 C9 O3 117.4(3) . . ? C10 C9 C8 122.2(3) . . ? O3 C9 C8 120.3(3) . . ? C9 C10 C11 118.9(4) . . ? O4 C11 C12 123.7(3) . . ? O4 C11 C10 115.5(3) . . ? C12 C11 C10 120.8(4) . . ? C13 C12 C11 119.1(3) . . ? C12 C13 C8 121.9(4) . . ? O5 C15 C2 108.7(3) . . ? C17 C16 C21 118.7(4) . . ? C17 C16 O5 125.4(4) . . ? C21 C16 O5 115.9(3) . . ? C16 C17 C18 119.4(4) . . ? C19 C18 C17 123.8(4) . . ? C18 C19 C20 115.5(4) . . ? C18 C19 C22 123.2(4) . . ? C20 C19 C22 121.3(4) . . ? C21 C20 C19 121.8(4) . . ? C16 C21 C20 120.7(4) . . ? C23 C22 C24 116.3(6) . . ? C23 C22 C19 110.7(4) . . ? C24 C22 C19 112.9(4) . . ? C23 C22 C25 106.5(7) . . ? C24 C22 C25 99.9(5) . . ? C19 C22 C25 109.6(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 0.784 _refine_diff_density_min -0.377 _refine_diff_density_rms 0.124